data_240401cx
_audit_creation_date               2024-04-01
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C20 H16 Br N O2'
_chemical_formula_sum              'C20 H16 Br N O2'
_chemical_formula_weight           382.25
_chemical_absolute_configuration   rmad
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0137 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Br' 'Br' -0.9338 1.0006
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             4
_space_group_name_H-M_alt          'P 1 21 1'
_space_group_name_Hall             'P 2yb'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z'

_cell_length_a                     7.1741(4)
_cell_length_b                     10.3025(6)
_cell_length_c                     22.7770(11)
_cell_angle_alpha                  90
_cell_angle_beta                   92.447(2)
_cell_angle_gamma                  90
_cell_volume                       1681.94(16)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      9904
_cell_measurement_temperature      170.00
_cell_measurement_theta_max        54.855
_cell_measurement_theta_min        3.381
_shelx_estimated_absorpt_T_max     0.896
_shelx_estimated_absorpt_T_min     0.700
_exptl_absorpt_coefficient_mu      2.257
_exptl_absorpt_correction_T_max    0.7508
_exptl_absorpt_correction_T_min    0.4593
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1434 before and 0.0794 after correction.
The Ratio of minimum to maximum transmission is 0.6117.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.510
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               776
_exptl_crystal_size_max            0.17
_exptl_crystal_size_mid            0.17
_exptl_crystal_size_min            0.05
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0579
_diffrn_reflns_av_unetI/netI       0.0613
_diffrn_reflns_Laue_measured_fraction_full  0.996
_diffrn_reflns_Laue_measured_fraction_max  0.992
_diffrn_reflns_limit_h_max         8
_diffrn_reflns_limit_h_min         -8
_diffrn_reflns_limit_k_max         12
_diffrn_reflns_limit_k_min         -12
_diffrn_reflns_limit_l_max         27
_diffrn_reflns_limit_l_min         -26
_diffrn_reflns_number              16379
_diffrn_reflns_point_group_measured_fraction_full  0.942
_diffrn_reflns_point_group_measured_fraction_max  0.930
_diffrn_reflns_theta_full          53.594
_diffrn_reflns_theta_max           54.972
_diffrn_reflns_theta_min           3.379
_diffrn_ambient_temperature        170.00
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.996
_diffrn_measured_fraction_theta_max  0.992
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             GaK\a
_diffrn_radiation_wavelength       1.34139
_diffrn_source                     ?
_diffrn_source_current             2.86
_diffrn_source_power               0.1995708
_diffrn_source_voltage             69.78
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.772
_reflns_Friedel_fraction_full      0.881
_reflns_Friedel_fraction_max       0.861
_reflns_number_gt                  5134
_reflns_number_total               5997
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT V8.40B (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics      'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max           1.398
_refine_diff_density_min           -0.819
_refine_diff_density_rms           0.113
_refine_ls_abs_structure_details
;
 Flack x determined using 1816 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.061(17)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.098
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       476
_refine_ls_number_reflns           5997
_refine_ls_number_restraints       190
_refine_ls_R_factor_all            0.0740
_refine_ls_R_factor_gt             0.0630
_refine_ls_restrained_S_all        1.086
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.1093P)²+1.9741P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1806
_refine_ls_wR_factor_ref           0.1883
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
 C14A-C15A \\sim C14A-C15B
 with sigma of 0.02
 C15A-C16A \\sim C15B-C16B
 with sigma of 0.02
 C15A-C20A \\sim C15B-C20B
 with sigma of 0.02
 C16A-C17A \\sim C16B-C17B
 with sigma of 0.02
 C17A-C18A \\sim C17B-C18B
 with sigma of 0.02
 C18A-C19A \\sim C18B-C19B
 with sigma of 0.02
 C19A-C20A \\sim C19B-C20B
 with sigma of 0.02
 C14A-C16A \\sim C14A-C16B
 with sigma of 0.04
 C14A-C20A \\sim C14A-C20B
 with sigma of 0.04
 C15A-C17A \\sim C15B-C17B
 with sigma of 0.04
 C15A-C19A \\sim C15B-C19B
 with sigma of 0.04
 C16A-C18A \\sim C16B-C18B
 with sigma of 0.04
 C16A-C20A \\sim C16B-C20B
 with sigma of 0.04
 C17A-C19A \\sim C17B-C19B
 with sigma of 0.04
 C18A-C20A \\sim C18B-C20B
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C15B \\sim C15A \\sim C16B \\sim C16A \\sim C17A \\sim C17B \\sim C18A \\sim
C18B \\sim C19B \\sim C19A \\sim C20A \\sim C20B: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(H14C)=Sof(H14D)=Sof(C15B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=Sof(H17B)=
 Sof(C18B)=Sof(H18B)=Sof(C19B)=Sof(H19B)=Sof(C20B)=Sof(H20B)=1-FVAR(1)
 Sof(H14A)=Sof(H14B)=Sof(C15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17A)=
 Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C13(H13C,H13D), C14(H14E,H14F), C4A(H4AA,H4AB), C13A(H13A,H13B),
 C14A(H14A,H14B), C14A(H14C,H14D)
5.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20),
 C8A(H8A), C9A(H9A), C11A(H11A), C16A(H16A), C17A(H17A), C18A(H18A), C19A(H19A),
  C20A(H20A), C16B(H16B), C17B(H17B), C18B(H18B), C19B(H19B), C20B(H20B)
5.c Fitted hexagon refined as free rotating group:
 C15B(C16B,C17B,C18B,C19B,C20B)
5.d X=CH2 refined with riding coordinates:
 C3(H3A,H3B), C3A(H3AA,H3AB)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 Br1 Br -0.07816(16) 0.44708(15) 0.32098(5) 0.0630(4) Uani 1 1 d . . . . .
 O1 O 0.5385(13) 0.5124(11) 0.5892(3) 0.076(3) Uani 1 1 d . . . . .
 O2 O 0.7965(10) 0.5565(6) 0.4586(3) 0.0420(15) Uani 1 1 d . . . . .
 N1 N 0.8347(12) 0.4249(8) 0.5880(3) 0.0414(18) Uani 1 1 d . . . . .
 C1 C 0.6330(12) 0.3787(9) 0.5066(3) 0.0333(17) Uani 1 1 d . . . . .
 C2 C 0.7973(11) 0.2855(8) 0.5074(3) 0.0286(16) Uani 1 1 d . . . . .
 C3 C 0.8165(14) 0.1798(9) 0.4753(4) 0.040(2) Uani 1 1 d . . . . .
 H3A H 0.926133 0.128486 0.480104 0.048 Uiso 1 1 calc R U . . .
 H3B H 0.720775 0.155221 0.447400 0.048 Uiso 1 1 calc R U . . .
 C4 C 0.9407(12) 0.3337(9) 0.5531(4) 0.0352(19) Uani 1 1 d . . . . .
 H4A H 0.990765 0.261387 0.577647 0.042 Uiso 1 1 calc R U . . .
 H4B H 1.045329 0.377939 0.534356 0.042 Uiso 1 1 calc R U . . .
 C5 C 0.6593(14) 0.4456(11) 0.5665(4) 0.045(2) Uani 1 1 d . . . . .
 C6 C 0.6622(11) 0.4869(7) 0.4610(3) 0.0271(16) Uani 1 1 d . . . . .
 C7 C 0.4880(11) 0.4939(7) 0.4231(3) 0.0277(16) Uani 1 1 d . . . . .
 C8 C 0.4465(15) 0.5772(9) 0.3759(4) 0.039(2) Uani 1 1 d . . . . .
 H8 H 0.533499 0.641000 0.364488 0.047 Uiso 1 1 calc R U . . .
 C9 C 0.2754(15) 0.5641(10) 0.3463(4) 0.044(2) Uani 1 1 d . . . . .
 H9 H 0.241767 0.619526 0.314204 0.053 Uiso 1 1 calc R U . . .
 C10 C 0.1544(14) 0.4695(10) 0.3639(4) 0.044(2) Uani 1 1 d . . . . .
 C11 C 0.1910(13) 0.3861(10) 0.4116(4) 0.040(2) Uani 1 1 d . . . . .
 H11 H 0.102877 0.323296 0.423253 0.048 Uiso 1 1 calc R U . . .
 C12 C 0.3622(12) 0.4003(9) 0.4406(4) 0.0333(18) Uani 1 1 d . . . . .
 C13 C 0.4408(12) 0.3226(11) 0.4924(4) 0.044(2) Uani 1 1 d . . . . .
 H13C H 0.449706 0.229540 0.482069 0.053 Uiso 1 1 calc R U . . .
 H13D H 0.360505 0.331398 0.526502 0.053 Uiso 1 1 calc R U . . .
 C14 C 0.9126(18) 0.4888(9) 0.6394(4) 0.050(3) Uani 1 1 d . . . . .
 H14E H 0.830990 0.562481 0.649103 0.060 Uiso 1 1 calc R U . . .
 H14F H 1.036002 0.524744 0.630201 0.060 Uiso 1 1 calc R U . . .
 C15 C 0.936(2) 0.4022(10) 0.6925(4) 0.055(3) Uani 1 1 d . . . . .
 C16 C 1.099(2) 0.3413(13) 0.7079(6) 0.073(4) Uani 1 1 d . . . . .
 H16 H 1.205773 0.351704 0.684987 0.087 Uiso 1 1 calc R U . . .
 C17 C 1.107(3) 0.2610(14) 0.7595(8) 0.099(7) Uani 1 1 d . . . . .
 H17 H 1.219911 0.217690 0.770957 0.119 Uiso 1 1 calc R U . . .
 C18 C 0.954(4) 0.2469(15) 0.7919(7) 0.097(7) Uani 1 1 d . . . . .
 H18 H 0.960805 0.194196 0.826192 0.117 Uiso 1 1 calc R U . . .
 C19 C 0.796(3) 0.3056(13) 0.7764(6) 0.090(6) Uani 1 1 d . . . . .
 H19 H 0.691210 0.293433 0.799837 0.108 Uiso 1 1 calc R U . . .
 C20 C 0.778(3) 0.3859(11) 0.7263(5) 0.070(4) Uani 1 1 d . . . . .
 H20 H 0.662685 0.427306 0.715774 0.084 Uiso 1 1 calc R U . . .
 Br1A Br -0.52010(16) 0.51613(14) 1.17797(5) 0.0615(4) Uani 1 1 d . . . . .
 O1A O 0.0087(11) 0.4970(9) 0.9078(3) 0.062(2) Uani 1 1 d . . . . .
 O2A O 0.3111(9) 0.4421(6) 1.0349(3) 0.0403(13) Uani 1 1 d . . . . .
 N1A N 0.3036(12) 0.5863(8) 0.9089(3) 0.0408(18) Uani 1 1 d . . . . .
 C1A C 0.1296(12) 0.6238(9) 0.9918(3) 0.0307(17) Uani 1 1 d . . . . .
 C2A C 0.2943(11) 0.7150(7) 0.9921(3) 0.0268(16) Uani 1 1 d . . . . .
 C3A C 0.3214(13) 0.8190(8) 1.0251(4) 0.0372(19) Uani 1 1 d . . . . .
 H3AA H 0.231415 0.843234 1.052474 0.045 Uiso 1 1 calc R U . . .
 H3AB H 0.431048 0.869607 1.021543 0.045 Uiso 1 1 calc R U . . .
 C4A C 0.4231(12) 0.6672(8) 0.9459(4) 0.0321(17) Uani 1 1 d . . . . .
 H4AA H 0.473839 0.740410 0.923466 0.038 Uiso 1 1 calc R U . . .
 H4AB H 0.527914 0.616498 0.963961 0.038 Uiso 1 1 calc R U . . .
 C5A C 0.1327(14) 0.5623(9) 0.9309(4) 0.040(2) Uani 1 1 d . . . . .
 C6A C 0.1737(11) 0.5094(8) 1.0348(3) 0.0289(15) Uani 1 1 d . . . . .
 C7A C 0.0138(12) 0.4986(8) 1.0727(3) 0.0285(16) Uani 1 1 d . . . . .
 C8A C -0.0094(14) 0.4073(8) 1.1185(3) 0.0351(19) Uani 1 1 d . . . . .
 H8A H 0.083450 0.343974 1.127882 0.042 Uiso 1 1 calc R U . . .
 C9A C -0.1710(13) 0.4138(9) 1.1490(4) 0.038(2) Uani 1 1 d . . . . .
 H9A H -0.191248 0.354885 1.180197 0.045 Uiso 1 1 calc R U . . .
 C10A C -0.3035(13) 0.5070(10) 1.1337(4) 0.041(2) Uani 1 1 d . . . . .
 C11A C -0.2825(13) 0.5984(9) 1.0887(4) 0.0372(19) Uani 1 1 d . . . . .
 H11A H -0.374938 0.662088 1.079363 0.045 Uiso 1 1 calc R U . . .
 C12A C -0.1184(11) 0.5901(8) 1.0586(3) 0.0283(16) Uani 1 1 d . . . . .
 C13A C -0.0596(12) 0.6755(10) 1.0085(4) 0.039(2) Uani 1 1 d . . . . .
 H13A H -0.049636 0.767196 1.021166 0.046 Uiso 1 1 calc R U . . .
 H13B H -0.150949 0.669596 0.974755 0.046 Uiso 1 1 calc R U . . .
 C14A C 0.3729(18) 0.5084(11) 0.8603(4) 0.054(3) Uani 1 1 d D . . . .
 H14A H 0.270868 0.452063 0.844483 0.065 Uiso 0.51(2) 1 calc R U P A 1
 H14B H 0.474860 0.451501 0.875675 0.065 Uiso 0.51(2) 1 calc R U P A 1
 H14C H 0.269170 0.455661 0.842951 0.065 Uiso 0.49(2) 1 calc R U P A 2
 H14D H 0.470289 0.448134 0.875945 0.065 Uiso 0.49(2) 1 calc R U P A 2
 C15A C 0.444(3) 0.589(3) 0.8113(9) 0.036(3) Uani 0.51(2) 1 d D U P A 1
 C16A C 0.619(3) 0.642(2) 0.8076(9) 0.043(3) Uani 0.51(2) 1 d D U P A 1
 H16A H 0.705241 0.630157 0.840030 0.051 Uiso 0.51(2) 1 calc R U P A 1
 C17A C 0.678(3) 0.711(2) 0.7591(9) 0.046(3) Uani 0.51(2) 1 d D U P A 1
 H17A H 0.802381 0.741174 0.756154 0.056 Uiso 0.51(2) 1 calc R U P A 1
 C18A C 0.542(4) 0.733(2) 0.7157(8) 0.046(4) Uani 0.51(2) 1 d D U P A 1
 H18A H 0.570953 0.786492 0.683482 0.056 Uiso 0.51(2) 1 calc R U P A 1
 C19A C 0.364(4) 0.681(2) 0.7167(9) 0.050(4) Uani 0.51(2) 1 d D U P A 1
 H19A H 0.279017 0.692747 0.684135 0.060 Uiso 0.51(2) 1 calc R U P A 1
 C20A C 0.311(3) 0.611(2) 0.7655(10) 0.045(3) Uani 0.51(2) 1 d D U P A 1
 H20A H 0.187370 0.578276 0.767662 0.054 Uiso 0.51(2) 1 calc R U P A 1
 C15B C 0.453(3) 0.591(2) 0.8128(8) 0.035(3) Uani 0.49(2) 1 d DG U P A 2
 C16B C 0.642(3) 0.616(2) 0.8215(7) 0.043(3) Uani 0.49(2) 1 d DG U P A 2
 H16B H 0.707219 0.587374 0.856374 0.052 Uiso 0.49(2) 1 calc R U P A 2
 C17B C 0.737(2) 0.6842(18) 0.7793(8) 0.049(4) Uani 0.49(2) 1 d DG U P A 2
 H17B H 0.866568 0.701690 0.785262 0.058 Uiso 0.49(2) 1 calc R U P A 2
 C18B C 0.642(3) 0.7264(16) 0.7283(7) 0.048(4) Uani 0.49(2) 1 d DG U P A 2
 H18B H 0.707124 0.772810 0.699439 0.058 Uiso 0.49(2) 1 calc R U P A 2
 C19B C 0.453(3) 0.7007(17) 0.7196(6) 0.048(3) Uani 0.49(2) 1 d DG U P A 2
 H19B H 0.388329 0.729615 0.684728 0.057 Uiso 0.49(2) 1 calc R U P A 2
 C20B C 0.358(2) 0.633(2) 0.7618(8) 0.042(3) Uani 0.49(2) 1 d DG U P A 2
 H20B H 0.228976 0.615299 0.755840 0.051 Uiso 0.49(2) 1 calc R U P A 2


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 Br1 C10 1.911(9) . ?
 O1 C5 1.237(12) . ?
 O2 C6 1.204(10) . ?
 N1 C4 1.465(11) . ?
 N1 C5 1.348(12) . ?
 N1 C14 1.434(12) . ?
 C1 C2 1.520(11) . ?
 C1 C5 1.532(12) . ?
 C1 C6 1.544(11) . ?
 C1 C13 1.517(13) . ?
 C2 C3 1.322(13) . ?
 C2 C4 1.516(11) . ?
 C3 H3A 0.9500 . ?
 C3 H3B 0.9500 . ?
 C4 H4A 0.9900 . ?
 C4 H4B 0.9900 . ?
 C6 C7 1.490(10) . ?
 C7 C8 1.397(12) . ?
 C7 C12 1.391(12) . ?
 C8 H8 0.9500 . ?
 C8 C9 1.382(14) . ?
 C9 H9 0.9500 . ?
 C9 C10 1.376(16) . ?
 C10 C11 1.402(13) . ?
 C11 H11 0.9500 . ?
 C11 C12 1.377(13) . ?
 C12 C13 1.515(12) . ?
 C13 H13C 0.9900 . ?
 C13 H13D 0.9900 . ?
 C14 H14E 0.9900 . ?
 C14 H14F 0.9900 . ?
 C14 C15 1.507(14) . ?
 C15 C16 1.361(19) . ?
 C15 C20 1.41(2) . ?
 C16 H16 0.9500 . ?
 C16 C17 1.44(2) . ?
 C17 H17 0.9500 . ?
 C17 C18 1.36(3) . ?
 C18 H18 0.9500 . ?
 C18 C19 1.32(3) . ?
 C19 H19 0.9500 . ?
 C19 C20 1.411(18) . ?
 C20 H20 0.9500 . ?
 Br1A C10A 1.890(9) . ?
 O1A C5A 1.217(12) . ?
 O2A C6A 1.205(10) . ?
 N1A C4A 1.442(11) . ?
 N1A C5A 1.367(13) . ?
 N1A C14A 1.471(12) . ?
 C1A C2A 1.510(11) . ?
 C1A C5A 1.525(12) . ?
 C1A C6A 1.556(11) . ?
 C1A C13A 1.522(13) . ?
 C2A C3A 1.318(12) . ?
 C2A C4A 1.512(12) . ?
 C3A H3AA 0.9500 . ?
 C3A H3AB 0.9500 . ?
 C4A H4AA 0.9900 . ?
 C4A H4AB 0.9900 . ?
 C6A C7A 1.469(11) . ?
 C7A C8A 1.420(11) . ?
 C7A C12A 1.366(12) . ?
 C8A H8A 0.9500 . ?
 C8A C9A 1.378(14) . ?
 C9A H9A 0.9500 . ?
 C9A C10A 1.385(15) . ?
 C10A C11A 1.406(13) . ?
 C11A H11A 0.9500 . ?
 C11A C12A 1.390(13) . ?
 C12A C13A 1.515(12) . ?
 C13A H13A 0.9900 . ?
 C13A H13B 0.9900 . ?
 C14A H14A 0.9900 . ?
 C14A H14B 0.9900 . ?
 C14A H14C 0.9900 . ?
 C14A H14D 0.9900 . ?
 C14A C15A 1.496(17) . ?
 C14A C15B 1.506(14) . ?
 C15A C16A 1.38(2) . ?
 C15A C20A 1.400(19) . ?
 C16A H16A 0.9500 . ?
 C16A C17A 1.40(2) . ?
 C17A H17A 0.9500 . ?
 C17A C18A 1.38(2) . ?
 C18A H18A 0.9500 . ?
 C18A C19A 1.38(2) . ?
 C19A H19A 0.9500 . ?
 C19A C20A 1.39(2) . ?
 C20A H20A 0.9500 . ?
 C15B C16B 1.3900 . ?
 C15B C20B 1.3900 . ?
 C16B H16B 0.9500 . ?
 C16B C17B 1.3900 . ?
 C17B H17B 0.9500 . ?
 C17B C18B 1.3900 . ?
 C18B H18B 0.9500 . ?
 C18B C19B 1.3900 . ?
 C19B H19B 0.9500 . ?
 C19B C20B 1.3900 . ?
 C20B H20B 0.9500 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C5 N1 C4 113.7(7) . . ?
 C5 N1 C14 123.3(8) . . ?
 C14 N1 C4 122.9(8) . . ?
 C2 C1 C5 102.0(6) . . ?
 C2 C1 C6 109.7(7) . . ?
 C5 C1 C6 105.0(8) . . ?
 C13 C1 C2 117.3(8) . . ?
 C13 C1 C5 115.9(8) . . ?
 C13 C1 C6 106.3(7) . . ?
 C3 C2 C1 127.8(8) . . ?
 C3 C2 C4 124.5(8) . . ?
 C4 C2 C1 107.7(7) . . ?
 C2 C3 H3A 120.0 . . ?
 C2 C3 H3B 120.0 . . ?
 H3A C3 H3B 120.0 . . ?
 N1 C4 C2 103.3(7) . . ?
 N1 C4 H4A 111.1 . . ?
 N1 C4 H4B 111.1 . . ?
 C2 C4 H4A 111.1 . . ?
 C2 C4 H4B 111.1 . . ?
 H4A C4 H4B 109.1 . . ?
 O1 C5 N1 126.5(9) . . ?
 O1 C5 C1 124.1(9) . . ?
 N1 C5 C1 109.3(7) . . ?
 O2 C6 C1 126.3(7) . . ?
 O2 C6 C7 126.7(7) . . ?
 C7 C6 C1 106.9(7) . . ?
 C8 C7 C6 128.4(8) . . ?
 C12 C7 C6 109.7(7) . . ?
 C12 C7 C8 121.9(8) . . ?
 C7 C8 H8 121.0 . . ?
 C9 C8 C7 118.1(9) . . ?
 C9 C8 H8 121.0 . . ?
 C8 C9 H9 120.5 . . ?
 C10 C9 C8 119.0(8) . . ?
 C10 C9 H9 120.5 . . ?
 C9 C10 Br1 119.0(7) . . ?
 C9 C10 C11 124.1(9) . . ?
 C11 C10 Br1 116.9(8) . . ?
 C10 C11 H11 121.9 . . ?
 C12 C11 C10 116.1(9) . . ?
 C12 C11 H11 121.9 . . ?
 C7 C12 C13 111.5(8) . . ?
 C11 C12 C7 120.8(8) . . ?
 C11 C12 C13 127.7(8) . . ?
 C1 C13 H13C 110.6 . . ?
 C1 C13 H13D 110.6 . . ?
 C12 C13 C1 105.6(7) . . ?
 C12 C13 H13C 110.6 . . ?
 C12 C13 H13D 110.6 . . ?
 H13C C13 H13D 108.8 . . ?
 N1 C14 H14E 108.7 . . ?
 N1 C14 H14F 108.7 . . ?
 N1 C14 C15 114.2(8) . . ?
 H14E C14 H14F 107.6 . . ?
 C15 C14 H14E 108.7 . . ?
 C15 C14 H14F 108.7 . . ?
 C16 C15 C14 123.1(14) . . ?
 C16 C15 C20 120.6(12) . . ?
 C20 C15 C14 116.4(11) . . ?
 C15 C16 H16 120.6 . . ?
 C15 C16 C17 118.7(18) . . ?
 C17 C16 H16 120.6 . . ?
 C16 C17 H17 119.9 . . ?
 C18 C17 C16 120.1(17) . . ?
 C18 C17 H17 119.9 . . ?
 C17 C18 H18 119.7 . . ?
 C19 C18 C17 120.7(15) . . ?
 C19 C18 H18 119.6 . . ?
 C18 C19 H19 118.8 . . ?
 C18 C19 C20 122(2) . . ?
 C20 C19 H19 118.8 . . ?
 C15 C20 C19 117.5(16) . . ?
 C15 C20 H20 121.3 . . ?
 C19 C20 H20 121.3 . . ?
 C4A N1A C14A 123.0(9) . . ?
 C5A N1A C4A 114.1(7) . . ?
 C5A N1A C14A 121.0(8) . . ?
 C2A C1A C5A 102.7(7) . . ?
 C2A C1A C6A 109.3(7) . . ?
 C2A C1A C13A 119.2(8) . . ?
 C5A C1A C6A 104.4(7) . . ?
 C13A C1A C5A 114.8(8) . . ?
 C13A C1A C6A 105.5(6) . . ?
 C1A C2A C4A 107.2(7) . . ?
 C3A C2A C1A 127.2(8) . . ?
 C3A C2A C4A 125.6(8) . . ?
 C2A C3A H3AA 120.0 . . ?
 C2A C3A H3AB 120.0 . . ?
 H3AA C3A H3AB 120.0 . . ?
 N1A C4A C2A 103.3(7) . . ?
 N1A C4A H4AA 111.1 . . ?
 N1A C4A H4AB 111.1 . . ?
 C2A C4A H4AA 111.1 . . ?
 C2A C4A H4AB 111.1 . . ?
 H4AA C4A H4AB 109.1 . . ?
 O1A C5A N1A 126.3(9) . . ?
 O1A C5A C1A 125.7(9) . . ?
 N1A C5A C1A 107.9(7) . . ?
 O2A C6A C1A 125.5(7) . . ?
 O2A C6A C7A 128.0(8) . . ?
 C7A C6A C1A 106.5(7) . . ?
 C8A C7A C6A 126.9(8) . . ?
 C12A C7A C6A 111.2(7) . . ?
 C12A C7A C8A 121.9(8) . . ?
 C7A C8A H8A 121.1 . . ?
 C9A C8A C7A 117.7(8) . . ?
 C9A C8A H8A 121.1 . . ?
 C8A C9A H9A 120.3 . . ?
 C8A C9A C10A 119.4(8) . . ?
 C10A C9A H9A 120.3 . . ?
 C9A C10A Br1A 118.2(7) . . ?
 C9A C10A C11A 123.6(9) . . ?
 C11A C10A Br1A 118.1(8) . . ?
 C10A C11A H11A 122.0 . . ?
 C12A C11A C10A 116.0(9) . . ?
 C12A C11A H11A 122.0 . . ?
 C7A C12A C11A 121.4(8) . . ?
 C7A C12A C13A 111.4(7) . . ?
 C11A C12A C13A 127.2(8) . . ?
 C1A C13A H13A 110.7 . . ?
 C1A C13A H13B 110.7 . . ?
 C12A C13A C1A 105.4(7) . . ?
 C12A C13A H13A 110.7 . . ?
 C12A C13A H13B 110.7 . . ?
 H13A C13A H13B 108.8 . . ?
 N1A C14A H14A 108.9 . . ?
 N1A C14A H14B 108.9 . . ?
 N1A C14A H14C 109.1 . . ?
 N1A C14A H14D 109.1 . . ?
 N1A C14A C15A 113.2(15) . . ?
 N1A C14A C15B 112.7(13) . . ?
 H14A C14A H14B 107.7 . . ?
 H14C C14A H14D 107.8 . . ?
 C15A C14A H14A 108.9 . . ?
 C15A C14A H14B 108.9 . . ?
 C15B C14A H14C 109.1 . . ?
 C15B C14A H14D 109.1 . . ?
 C16A C15A C14A 127.2(17) . . ?
 C16A C15A C20A 119.1(15) . . ?
 C20A C15A C14A 113.7(17) . . ?
 C15A C16A H16A 118.0 . . ?
 C15A C16A C17A 123.9(17) . . ?
 C17A C16A H16A 118.0 . . ?
 C16A C17A H17A 122.6 . . ?
 C18A C17A C16A 114.9(18) . . ?
 C18A C17A H17A 122.6 . . ?
 C17A C18A H18A 118.3 . . ?
 C17A C18A C19A 123.4(17) . . ?
 C19A C18A H18A 118.3 . . ?
 C18A C19A H19A 120.0 . . ?
 C18A C19A C20A 120.0(17) . . ?
 C20A C19A H19A 120.0 . . ?
 C15A C20A H20A 120.8 . . ?
 C19A C20A C15A 118.3(17) . . ?
 C19A C20A H20A 120.8 . . ?
 C16B C15B C14A 113.9(13) . . ?
 C16B C15B C20B 120.0 . . ?
 C20B C15B C14A 126.0(13) . . ?
 C15B C16B H16B 120.0 . . ?
 C15B C16B C17B 120.0 . . ?
 C17B C16B H16B 120.0 . . ?
 C16B C17B H17B 120.0 . . ?
 C18B C17B C16B 120.0 . . ?
 C18B C17B H17B 120.0 . . ?
 C17B C18B H18B 120.0 . . ?
 C17B C18B C19B 120.0 . . ?
 C19B C18B H18B 120.0 . . ?
 C18B C19B H19B 120.0 . . ?
 C20B C19B C18B 120.0 . . ?
 C20B C19B H19B 120.0 . . ?
 C15B C20B H20B 120.0 . . ?
 C19B C20B C15B 120.0 . . ?
 C19B C20B H20B 120.0 . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 Br1 C10 C11 C12 177.7(7) . . . . ?
 O2 C6 C7 C8 3.0(13) . . . . ?
 O2 C6 C7 C12 -177.7(8) . . . . ?
 N1 C14 C15 C16 95.7(14) . . . . ?
 N1 C14 C15 C20 -83.9(12) . . . . ?
 C1 C2 C4 N1 16.4(9) . . . . ?
 C1 C6 C7 C8 179.5(8) . . . . ?
 C1 C6 C7 C12 -1.2(9) . . . . ?
 C2 C1 C5 O1 -166.2(11) . . . . ?
 C2 C1 C5 N1 16.7(11) . . . . ?
 C2 C1 C6 O2 -54.2(11) . . . . ?
 C2 C1 C6 C7 129.3(7) . . . . ?
 C2 C1 C13 C12 -124.4(8) . . . . ?
 C3 C2 C4 N1 -163.0(9) . . . . ?
 C4 N1 C5 O1 175.9(12) . . . . ?
 C4 N1 C5 C1 -7.1(12) . . . . ?
 C4 N1 C14 C15 -74.2(14) . . . . ?
 C5 N1 C4 C2 -5.9(11) . . . . ?
 C5 N1 C14 C15 107.7(12) . . . . ?
 C5 C1 C2 C3 159.5(10) . . . . ?
 C5 C1 C2 C4 -20.0(9) . . . . ?
 C5 C1 C6 O2 54.7(10) . . . . ?
 C5 C1 C6 C7 -121.8(7) . . . . ?
 C5 C1 C13 C12 114.9(9) . . . . ?
 C6 C1 C2 C3 -89.6(11) . . . . ?
 C6 C1 C2 C4 91.0(8) . . . . ?
 C6 C1 C5 O1 79.4(13) . . . . ?
 C6 C1 C5 N1 -97.7(9) . . . . ?
 C6 C1 C13 C12 -1.3(10) . . . . ?
 C6 C7 C8 C9 178.8(8) . . . . ?
 C6 C7 C12 C11 -178.9(8) . . . . ?
 C6 C7 C12 C13 0.4(10) . . . . ?
 C7 C8 C9 C10 -0.6(14) . . . . ?
 C7 C12 C13 C1 0.6(11) . . . . ?
 C8 C7 C12 C11 0.4(13) . . . . ?
 C8 C7 C12 C13 179.7(8) . . . . ?
 C8 C9 C10 Br1 -177.6(7) . . . . ?
 C8 C9 C10 C11 1.8(15) . . . . ?
 C9 C10 C11 C12 -1.8(14) . . . . ?
 C10 C11 C12 C7 0.6(13) . . . . ?
 C10 C11 C12 C13 -178.6(9) . . . . ?
 C11 C12 C13 C1 179.9(9) . . . . ?
 C12 C7 C8 C9 -0.4(13) . . . . ?
 C13 C1 C2 C3 31.7(13) . . . . ?
 C13 C1 C2 C4 -147.7(8) . . . . ?
 C13 C1 C5 O1 -37.5(15) . . . . ?
 C13 C1 C5 N1 145.4(9) . . . . ?
 C13 C1 C6 O2 178.1(8) . . . . ?
 C13 C1 C6 C7 1.6(9) . . . . ?
 C14 N1 C4 C2 175.9(8) . . . . ?
 C14 N1 C5 O1 -5.9(18) . . . . ?
 C14 N1 C5 C1 171.2(9) . . . . ?
 C14 C15 C16 C17 179.9(11) . . . . ?
 C14 C15 C20 C19 -179.8(10) . . . . ?
 C15 C16 C17 C18 0(2) . . . . ?
 C16 C15 C20 C19 0.6(17) . . . . ?
 C16 C17 C18 C19 0(2) . . . . ?
 C17 C18 C19 C20 0(2) . . . . ?
 C18 C19 C20 C15 0(2) . . . . ?
 C20 C15 C16 C17 -0.5(18) . . . . ?
 Br1A C10A C11A C12A 178.1(6) . . . . ?
 O2A C6A C7A C8A 1.6(14) . . . . ?
 O2A C6A C7A C12A -178.2(8) . . . . ?
 N1A C14A C15A C16A 85(3) . . . . ?
 N1A C14A C15A C20A -95.1(19) . . . . ?
 N1A C14A C15B C16B 89.5(15) . . . . ?
 N1A C14A C15B C20B -94.8(16) . . . . ?
 C1A C2A C4A N1A 19.7(9) . . . . ?
 C1A C6A C7A C8A 179.6(7) . . . . ?
 C1A C6A C7A C12A -0.2(9) . . . . ?
 C2A C1A C5A O1A -168.1(10) . . . . ?
 C2A C1A C5A N1A 16.0(10) . . . . ?
 C2A C1A C6A O2A -52.0(11) . . . . ?
 C2A C1A C6A C7A 130.0(7) . . . . ?
 C2A C1A C13A C12A -124.1(8) . . . . ?
 C3A C2A C4A N1A -159.1(8) . . . . ?
 C4A N1A C5A O1A -179.9(10) . . . . ?
 C4A N1A C5A C1A -4.0(11) . . . . ?
 C4A N1A C14A C15A -66.2(16) . . . . ?
 C4A N1A C14A C15B -63.1(15) . . . . ?
 C5A N1A C4A C2A -9.8(10) . . . . ?
 C5A N1A C14A C15A 130.2(13) . . . . ?
 C5A N1A C14A C15B 133.3(12) . . . . ?
 C5A C1A C2A C3A 157.0(9) . . . . ?
 C5A C1A C2A C4A -21.7(9) . . . . ?
 C5A C1A C6A O2A 57.4(11) . . . . ?
 C5A C1A C6A C7A -120.7(7) . . . . ?
 C5A C1A C13A C12A 113.5(8) . . . . ?
 C6A C1A C2A C3A -92.6(10) . . . . ?
 C6A C1A C2A C4A 88.7(8) . . . . ?
 C6A C1A C5A O1A 77.8(12) . . . . ?
 C6A C1A C5A N1A -98.1(8) . . . . ?
 C6A C1A C13A C12A -0.9(9) . . . . ?
 C6A C7A C8A C9A 180.0(8) . . . . ?
 C6A C7A C12A C11A 180.0(8) . . . . ?
 C6A C7A C12A C13A -0.3(10) . . . . ?
 C7A C8A C9A C10A 0.5(12) . . . . ?
 C7A C12A C13A C1A 0.8(10) . . . . ?
 C8A C7A C12A C11A 0.1(12) . . . . ?
 C8A C7A C12A C13A 179.8(7) . . . . ?
 C8A C9A C10A Br1A -178.2(6) . . . . ?
 C8A C9A C10A C11A -0.8(13) . . . . ?
 C9A C10A C11A C12A 0.8(13) . . . . ?
 C10A C11A C12A C7A -0.4(12) . . . . ?
 C10A C11A C12A C13A 180.0(8) . . . . ?
 C11A C12A C13A C1A -179.6(8) . . . . ?
 C12A C7A C8A C9A -0.2(12) . . . . ?
 C13A C1A C2A C3A 28.7(12) . . . . ?
 C13A C1A C2A C4A -150.0(7) . . . . ?
 C13A C1A C5A O1A -37.1(14) . . . . ?
 C13A C1A C5A N1A 146.9(8) . . . . ?
 C13A C1A C6A O2A 178.8(8) . . . . ?
 C13A C1A C6A C7A 0.7(9) . . . . ?
 C14A N1A C4A C2A -174.4(8) . . . . ?
 C14A N1A C5A O1A -15.0(16) . . . . ?
 C14A N1A C5A C1A 160.9(9) . . . . ?
 C14A C15A C16A C17A 177(3) . . . . ?
 C14A C15A C20A C19A -178(2) . . . . ?
 C14A C15B C16B C17B 176(2) . . . . ?
 C14A C15B C20B C19B -175(2) . . . . ?
 C15A C16A C17A C18A 5(3) . . . . ?
 C16A C15A C20A C19A 2(3) . . . . ?
 C16A C17A C18A C19A -6(3) . . . . ?
 C17A C18A C19A C20A 5(3) . . . . ?
 C18A C19A C20A C15A -3(3) . . . . ?
 C20A C15A C16A C17A -3(3) . . . . ?
 C15B C16B C17B C18B 0.0 . . . . ?
 C16B C15B C20B C19B 0.0 . . . . ?
 C16B C17B C18B C19B 0.0 . . . . ?
 C17B C18B C19B C20B 0.0 . . . . ?
 C18B C19B C20B C15B 0.0 . . . . ?
 C20B C15B C16B C17B 0.0 . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
