data_Gandelman80R
_audit_creation_date               2023-07-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number       '2014/7'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Bourhis, L.J., Dolomanov, O.V., Gildea, R.J., Howard, J.A.K., Puschmann, H.
 (2015). Acta Cryst. A71, 59-75.

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. C71, 3-8.
;
_chemical_name_common              'Gandelman80R (Aleksandr Koronatov)'
_chemical_name_systematic          ?
_chemical_formula_moiety           'C19 H24 F2 N2, 2(Cl) [+ solvent]'
_chemical_formula_sum              'C19 H24 Cl2 F2 N2 [+ solvent]'
_chemical_formula_weight           389.30
_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' 0.0181 0.0091 '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'
 'Cl' 'Cl' 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'F' 'F' 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0311 0.0180 '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             15
_space_group_name_H-M_alt          'C 1 2/c 1'
_space_group_name_Hall             '-C 2yc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                     30.0058(15)
_cell_length_b                     16.2260(5)
_cell_length_c                     9.7741(2)
_cell_angle_alpha                  90
_cell_angle_beta                   92.873(3)
_cell_angle_gamma                  90
_cell_volume                       4752.8(3)
_cell_formula_units_Z              8
_cell_measurement_reflns_used      4999
_cell_measurement_temperature      100.15
_cell_measurement_theta_max        80.244
_cell_measurement_theta_min        3.097
_shelx_estimated_absorpt_T_max     0.744
_shelx_estimated_absorpt_T_min     0.479
_exptl_absorpt_coefficient_mu      2.617
_exptl_absorpt_correction_T_max    0.724
_exptl_absorpt_correction_T_min    0.459
_exptl_absorpt_correction_type     analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.54a (Rigaku Oxford Diffraction, 2022)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colorless
_exptl_crystal_density_diffrn      1.088
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         needle
_exptl_crystal_F_000               1632
_exptl_crystal_size_max            0.33
_exptl_crystal_size_mid            0.15
_exptl_crystal_size_min            0.12
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0905
_diffrn_reflns_av_unetI/netI       0.0986
_diffrn_reflns_Laue_measured_fraction_full  0.983
_diffrn_reflns_Laue_measured_fraction_max  0.983
_diffrn_reflns_limit_h_max         37
_diffrn_reflns_limit_h_min         -38
_diffrn_reflns_limit_k_max         20
_diffrn_reflns_limit_k_min         -20
_diffrn_reflns_limit_l_max         12
_diffrn_reflns_limit_l_min         -7
_diffrn_reflns_number              22642
_diffrn_reflns_point_group_measured_fraction_full  0.983
_diffrn_reflns_point_group_measured_fraction_max  0.983
_diffrn_reflns_theta_full          67.684
_diffrn_reflns_theta_max           80.244
_diffrn_reflns_theta_min           3.097
_diffrn_ambient_temperature        100.15
_diffrn_detector_area_resol_mean   95
_diffrn_measured_fraction_theta_full  0.983
_diffrn_measured_fraction_theta_max  0.959
_diffrn_measurement_device_type    'XtaLAB Synergy-S'
_diffrn_measurement_method          'ω scans'
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54184
_diffrn_source                     ?
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  3333
_reflns_number_total               4999
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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         'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_collection         'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_reduction          'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution      'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max           0.893
_refine_diff_density_min           -0.384
_refine_diff_density_rms           0.081
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.042
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       361
_refine_ls_number_reflns           4999
_refine_ls_number_restraints       706
_refine_ls_R_factor_all            0.1058
_refine_ls_R_factor_gt             0.0822
_refine_ls_restrained_S_all        0.984
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.1398P)²+1.8495P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.2243
_refine_ls_wR_factor_ref           0.2499
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups, All N(H,H,H,H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
Uanis(C12A) = Uanis(C7)
4. Others
 Sof(C1A)=Sof(H1AA)=Sof(C2A)=Sof(H2AC)=Sof(H2AD)=Sof(C3A)=Sof(H3A)=Sof(C4A)=
 Sof(H4AA)=Sof(H4AB)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=1-FVAR(1)
 Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4A)=
 Sof(H4B)=Sof(C5)=Sof(H5A)=Sof(H5B)=FVAR(1)
 Sof(F2A)=Sof(H2BC)=Sof(H2BD)=Sof(C14A)=Sof(C19A)=Sof(H19A)=Sof(C18A)=
 Sof(H18A)=Sof(C17A)=Sof(C16A)=Sof(H16A)=Sof(C15A)=Sof(H15A)=1-FVAR(2)
 Sof(F2)=Sof(H2AA)=Sof(H2AB)=Sof(C14)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=
 Sof(C17)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=FVAR(2)
 Sof(F1A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(C11A)=Sof(H11A)=
 Sof(C12A)=Sof(H12A)=1-FVAR(3)
 Sof(F1)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(C11)=Sof(H11)=Sof(C12)=
 Sof(H12)=FVAR(3)
5.a Ternary CH refined with riding coordinates:
 C1(H1), C1A(H1AA), C3(H3), C3A(H3A)
5.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2AA,H2AB), N2(H2BC,H2BD), C2(H2A,H2B), C2A(H2AC,H2AD),
 C4(H4A,H4B), C4A(H4AA,H4AB), C5(H5A,H5B), C5A(H5AA,H5AB), C6(H6A,H6B),
 C13(H13A,H13B)
5.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C12(H12), C8A(H8A), C9A(H9A), C11A(H11A),
 C12A(H12A), C19A(H19A), C18A(H18A), C16A(H16A), C15A(H15A), C15(H15), C16(H16),
  C18(H18), C19(H19)
5.d Fitted hexagon refined as free rotating group:
 C7(C8,C9,C10,C11,C12), C14A(C19A,C18A,C17A,C16A,C15A)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       iterative
_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
 Cl1 Cl 0.34197(4) 0.25150(5) 0.25890(8) 0.0730(4) Uani 1 1 d . . . . .
 Cl2 Cl 0.25124(3) 0.50199(5) 0.30977(8) 0.0625(3) Uani 1 1 d . . . . .
 F1 F 0.4648(5) 0.4291(11) 0.1469(19) 0.145(5) Uani 0.67(3) 1 d . U P A 1
 F1A F 0.4654(10) 0.410(2) 0.085(5) 0.160(11) Uani 0.33(3) 1 d . U P A 2
 F2 F 0.4601(4) 1.0775(10) 0.403(2) 0.143(5) Uani 0.62(3) 1 d . U P B 1
 F2A F 0.4592(7) 1.0975(12) 0.493(4) 0.152(9) Uani 0.38(3) 1 d . U P B 2
 N1 N 0.31971(10) 0.60943(15) -0.0429(2) 0.0515(6) Uani 1 1 d . U . . .
 H1A H 0.3004 0.5770 -0.0933 0.062 Uiso 1 1 calc R U . . .
 H1B H 0.3290 0.6501 -0.0989 0.062 Uiso 1 1 calc R U . . .
 N2 N 0.31737(10) 0.88949(15) 0.5585(2) 0.0508(6) Uani 1 1 d . U . . .
 H2AA H 0.3277 0.8486 0.6153 0.061 Uiso 0.62(3) 1 calc R U P B 1
 H2AB H 0.2977 0.9201 0.6050 0.061 Uiso 0.62(3) 1 calc R U P B 1
 H2BC H 0.2975 0.9205 0.6035 0.061 Uiso 0.38(3) 1 calc R U P B 2
 H2BD H 0.3267 0.8481 0.6160 0.061 Uiso 0.38(3) 1 calc R U P B 2
 C1 C 0.3251(3) 0.7148(5) 0.1395(9) 0.049(2) Uani 0.504(5) 1 d . U P C 1
 H1 H 0.3450 0.7401 0.0719 0.059 Uiso 0.504(5) 1 calc R U P C 1
 C1A C 0.3222(3) 0.6917(5) 0.1832(9) 0.0458(18) Uani 0.496(5) 1 d . U P C 2
 H1AA H 0.3468 0.6550 0.2191 0.055 Uiso 0.496(5) 1 calc R U P C 2
 C2 C 0.2965(2) 0.7798(4) 0.2021(6) 0.0536(16) Uani 0.504(5) 1 d . U P C 1
 H2A H 0.2672 0.7564 0.2244 0.064 Uiso 0.504(5) 1 calc R U P C 1
 H2B H 0.2913 0.8263 0.1378 0.064 Uiso 0.504(5) 1 calc R U P C 1
 C2A C 0.2943(2) 0.7220(4) 0.3027(6) 0.0514(15) Uani 0.496(5) 1 d . U P C 2
 H2AC H 0.2655 0.7454 0.2679 0.062 Uiso 0.496(5) 1 calc R U P C 2
 H2AD H 0.2885 0.6764 0.3667 0.062 Uiso 0.496(5) 1 calc R U P C 2
 C3 C 0.3218(4) 0.8084(7) 0.3306(10) 0.049(2) Uani 0.504(5) 1 d . U P C 1
 H3 H 0.3466 0.8458 0.3057 0.059 Uiso 0.504(5) 1 calc R U P C 1
 C3A C 0.3237(4) 0.7883(6) 0.3731(10) 0.047(2) Uani 0.496(5) 1 d . U P C 2
 H3A H 0.3443 0.7631 0.4450 0.056 Uiso 0.496(5) 1 calc R U P C 2
 C4 C 0.3416(3) 0.7268(4) 0.3895(6) 0.0535(16) Uani 0.504(5) 1 d . U P C 1
 H4A H 0.3687 0.7375 0.4491 0.064 Uiso 0.504(5) 1 calc R U P C 1
 H4B H 0.3195 0.6973 0.4432 0.064 Uiso 0.504(5) 1 calc R U P C 1
 C4A C 0.3504(3) 0.8269(4) 0.2596(7) 0.0597(18) Uani 0.496(5) 1 d . U P C 2
 H4AA H 0.3826 0.8275 0.2866 0.072 Uiso 0.496(5) 1 calc R U P C 2
 H4AB H 0.3404 0.8841 0.2412 0.072 Uiso 0.496(5) 1 calc R U P C 2
 C5 C 0.3532(3) 0.6765(4) 0.2617(6) 0.0597(18) Uani 0.504(5) 1 d . U P C 1
 H5A H 0.3454 0.6177 0.2734 0.072 Uiso 0.504(5) 1 calc R U P C 1
 H5B H 0.3855 0.6806 0.2460 0.072 Uiso 0.504(5) 1 calc R U P C 1
 C5A C 0.3414(3) 0.7726(4) 0.1320(6) 0.0558(17) Uani 0.496(5) 1 d . U P C 2
 H5AA H 0.3199 0.7998 0.0665 0.067 Uiso 0.496(5) 1 calc R U P C 2
 H5AB H 0.3694 0.7624 0.0855 0.067 Uiso 0.496(5) 1 calc R U P C 2
 C6 C 0.29493(12) 0.6483(2) 0.0699(3) 0.0563(8) Uani 1 1 d . U . . .
 H6A H 0.2871 0.6060 0.1376 0.068 Uiso 1 1 calc R U . C 1
 H6B H 0.2670 0.6737 0.0319 0.068 Uiso 1 1 calc R U . C 1
 C7 C 0.35830(12) 0.55979(18) 0.0005(3) 0.0530(7) Uani 1 1 d G U . . .
 C8 C 0.40073(16) 0.5932(5) -0.0080(8) 0.066(2) Uani 0.67(3) 1 d G U P A 1
 H8 H 0.4044 0.6459 -0.0481 0.079 Uiso 0.67(3) 1 calc R U P A 1
 C9 C 0.43787(12) 0.5493(9) 0.0420(13) 0.082(3) Uani 0.67(3) 1 d G U P A 1
 H9 H 0.4669 0.5721 0.0361 0.099 Uiso 0.67(3) 1 calc R U P A 1
 C10 C 0.4326(3) 0.4721(9) 0.1005(15) 0.089(4) Uani 0.67(3) 1 d G U P A 1
 C11 C 0.3901(3) 0.4387(5) 0.1091(13) 0.066(3) Uani 0.67(3) 1 d G U P A 1
 H11 H 0.3865 0.3860 0.1492 0.079 Uiso 0.67(3) 1 calc R U P A 1
 C12 C 0.3530(2) 0.4826(3) 0.0591(8) 0.0553(16) Uani 0.67(3) 1 d G U P A 1
 H12 H 0.3240 0.4598 0.0650 0.066 Uiso 0.67(3) 1 calc R U P A 1
 C8A C 0.3993(7) 0.5819(14) -0.038(3) 0.078(5) Uani 0.33(3) 1 d . U P A 2
 H8A H 0.4029 0.6322 -0.0862 0.094 Uiso 0.33(3) 1 calc R U P A 2
 C9A C 0.4355(7) 0.5330(15) -0.009(4) 0.092(6) Uani 0.33(3) 1 d . U P A 2
 H9A H 0.4650 0.5469 -0.0316 0.111 Uiso 0.33(3) 1 calc R U P A 2
 C10A C 0.4244(9) 0.4601(13) 0.058(3) 0.081(5) Uani 0.33(3) 1 d . U P A 2
 C11A C 0.3821(10) 0.4313(12) 0.080(3) 0.067(5) Uani 0.33(3) 1 d . U P A 2
 H11A H 0.3771 0.3763 0.1089 0.080 Uiso 0.33(3) 1 calc R U P A 2
 C12A C 0.3473(8) 0.4864(9) 0.0577(19) 0.0530(7) Uani 0.33(3) 1 d . U P A 2
 H12A H 0.3177 0.4739 0.0808 0.064 Uiso 0.33(3) 1 calc R U P A 2
 C13 C 0.29319(12) 0.8515(2) 0.4369(3) 0.0543(7) Uani 1 1 d . U . . .
 H13A H 0.2755 0.8952 0.3889 0.065 Uiso 1 1 calc R U . C 1
 H13B H 0.2719 0.8105 0.4705 0.065 Uiso 1 1 calc R U . C 1
 C14 C 0.3563(5) 0.9439(10) 0.523(2) 0.053(3) Uani 0.62(3) 1 d . U P B 1
 C14A C 0.3531(6) 0.9375(16) 0.535(3) 0.049(4) Uani 0.38(3) 1 d G U P B 2
 C19A C 0.3464(7) 1.0119(18) 0.466(3) 0.053(4) Uani 0.38(3) 1 d G U P B 2
 H19A H 0.3176 1.0256 0.4285 0.063 Uiso 0.38(3) 1 calc R U P B 2
 C18A C 0.3817(8) 1.0661(13) 0.454(3) 0.079(6) Uani 0.38(3) 1 d G U P B 2
 H18A H 0.3771 1.1170 0.4068 0.095 Uiso 0.38(3) 1 calc R U P B 2
 C17A C 0.4239(7) 1.0460(11) 0.509(3) 0.099(6) Uani 0.38(3) 1 d G U P B 2
 C16A C 0.4307(6) 0.9717(12) 0.578(3) 0.104(6) Uani 0.38(3) 1 d G U P B 2
 H16A H 0.4595 0.9579 0.6155 0.125 Uiso 0.38(3) 1 calc R U P B 2
 C15A C 0.3953(7) 0.9174(11) 0.590(3) 0.073(5) Uani 0.38(3) 1 d G U P B 2
 H15A H 0.3999 0.8665 0.6372 0.088 Uiso 0.38(3) 1 calc R U P B 2
 C15 C 0.3989(5) 0.9128(8) 0.5439(17) 0.073(3) Uani 0.62(3) 1 d . U P B 1
 H15 H 0.4033 0.8604 0.5858 0.087 Uiso 0.62(3) 1 calc R U P B 1
 C16 C 0.4346(4) 0.9572(9) 0.505(2) 0.095(4) Uani 0.62(3) 1 d . U P B 1
 H16 H 0.4642 0.9368 0.5180 0.115 Uiso 0.62(3) 1 calc R U P B 1
 C17 C 0.4260(5) 1.0332(9) 0.4454(19) 0.094(4) Uani 0.62(3) 1 d . U P B 1
 C18 C 0.3842(6) 1.0649(9) 0.426(2) 0.075(3) Uani 0.62(3) 1 d . U P B 1
 H18 H 0.3800 1.1178 0.3862 0.089 Uiso 0.62(3) 1 calc R U P B 1
 C19 C 0.3483(6) 1.0202(12) 0.465(2) 0.059(3) Uani 0.62(3) 1 d . U P B 1
 H19 H 0.3188 1.0412 0.4521 0.071 Uiso 0.62(3) 1 calc R U P B 1


_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
 F1 C10 1.259(14) . ?
 F1A C10A 1.49(4) . ?
 F2 C17 1.335(16) . ?
 F2A C17A 1.37(2) . ?
 N1 H1A 0.9100 . ?
 N1 H1B 0.9100 . ?
 N1 C6 1.499(4) . ?
 N1 C7 1.456(4) . ?
 N2 H2AA 0.9100 . ?
 N2 H2AB 0.9100 . ?
 N2 H2BC 0.9100 . ?
 N2 H2BD 0.9100 . ?
 N2 C13 1.494(4) . ?
 N2 C14 1.518(14) . ?
 N2 C14A 1.355(16) . ?
 C1 H1 1.0000 . ?
 C1 C2 1.509(11) . ?
 C1 C5 1.557(10) . ?
 C1 C6 1.543(10) . ?
 C1A H1AA 1.0000 . ?
 C1A C2A 1.549(10) . ?
 C1A C5A 1.528(11) . ?
 C1A C6 1.517(9) . ?
 C2 H2A 0.9900 . ?
 C2 H2B 0.9900 . ?
 C2 C3 1.509(12) . ?
 C2A H2AC 0.9900 . ?
 C2A H2AD 0.9900 . ?
 C2A C3A 1.532(13) . ?
 C3 H3 1.0000 . ?
 C3 C4 1.549(11) . ?
 C3 C13 1.548(12) . ?
 C3A H3A 1.0000 . ?
 C3A C4A 1.534(11) . ?
 C3A C13 1.528(11) . ?
 C4 H4A 0.9900 . ?
 C4 H4B 0.9900 . ?
 C4 C5 1.547(8) . ?
 C4A H4AA 0.9900 . ?
 C4A H4AB 0.9900 . ?
 C4A C5A 1.540(9) . ?
 C5 H5A 0.9900 . ?
 C5 H5B 0.9900 . ?
 C5A H5AA 0.9900 . ?
 C5A H5AB 0.9900 . ?
 C6 H6A 0.9900 . ?
 C6 H6B 0.9900 . ?
 C7 C8 1.3900 . ?
 C7 C12 1.3900 . ?
 C7 C8A 1.353(19) . ?
 C7 C12A 1.363(14) . ?
 C8 H8 0.9500 . ?
 C8 C9 1.3900 . ?
 C9 H9 0.9500 . ?
 C9 C10 1.3900 . ?
 C10 C11 1.3900 . ?
 C11 H11 0.9500 . ?
 C11 C12 1.3900 . ?
 C12 H12 0.9500 . ?
 C8A H8A 0.9500 . ?
 C8A C9A 1.36(2) . ?
 C9A H9A 0.9500 . ?
 C9A C10A 1.40(2) . ?
 C10A C11A 1.38(2) . ?
 C11A H11A 0.9500 . ?
 C11A C12A 1.38(2) . ?
 C12A H12A 0.9500 . ?
 C13 H13A 0.9900 . ?
 C13 H13B 0.9900 . ?
 C14 C15 1.382(13) . ?
 C14 C19 1.376(9) . ?
 C14A C19A 1.3900 . ?
 C14A C15A 1.3900 . ?
 C19A H19A 0.9500 . ?
 C19A C18A 1.3900 . ?
 C18A H18A 0.9500 . ?
 C18A C17A 1.3900 . ?
 C17A C16A 1.3900 . ?
 C16A H16A 0.9500 . ?
 C16A C15A 1.3900 . ?
 C15A H15A 0.9500 . ?
 C15 H15 0.9500 . ?
 C15 C16 1.360(13) . ?
 C16 H16 0.9500 . ?
 C16 C17 1.383(13) . ?
 C17 C18 1.358(15) . ?
 C18 H18 0.9500 . ?
 C18 C19 1.367(12) . ?
 C19 H19 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
 H1A N1 H1B 107.4 . . ?
 C6 N1 H1A 108.3 . . ?
 C6 N1 H1B 108.3 . . ?
 C7 N1 H1A 108.3 . . ?
 C7 N1 H1B 108.3 . . ?
 C7 N1 C6 115.8(2) . . ?
 H2AA N2 H2AB 107.7 . . ?
 H2BC N2 H2BD 107.2 . . ?
 C13 N2 H2AA 108.8 . . ?
 C13 N2 H2AB 108.8 . . ?
 C13 N2 H2BC 108.0 . . ?
 C13 N2 H2BD 108.0 . . ?
 C13 N2 C14 113.8(8) . . ?
 C14 N2 H2AA 108.8 . . ?
 C14 N2 H2AB 108.8 . . ?
 C14A N2 H2BC 108.0 . . ?
 C14A N2 H2BD 108.0 . . ?
 C14A N2 C13 117.3(13) . . ?
 C2 C1 H1 110.6 . . ?
 C2 C1 C5 105.4(6) . . ?
 C2 C1 C6 109.5(7) . . ?
 C5 C1 H1 110.6 . . ?
 C6 C1 H1 110.6 . . ?
 C6 C1 C5 110.1(6) . . ?
 C2A C1A H1AA 110.0 . . ?
 C5A C1A H1AA 110.0 . . ?
 C5A C1A C2A 101.6(6) . . ?
 C6 C1A H1AA 110.0 . . ?
 C6 C1A C2A 114.0(7) . . ?
 C6 C1A C5A 111.0(6) . . ?
 C1 C2 H2A 110.5 . . ?
 C1 C2 H2B 110.5 . . ?
 C1 C2 C3 106.2(7) . . ?
 H2A C2 H2B 108.7 . . ?
 C3 C2 H2A 110.5 . . ?
 C3 C2 H2B 110.5 . . ?
 C1A C2A H2AC 111.0 . . ?
 C1A C2A H2AD 111.0 . . ?
 H2AC C2A H2AD 109.0 . . ?
 C3A C2A C1A 104.0(7) . . ?
 C3A C2A H2AC 111.0 . . ?
 C3A C2A H2AD 111.0 . . ?
 C2 C3 H3 109.5 . . ?
 C2 C3 C4 102.4(7) . . ?
 C2 C3 C13 115.0(8) . . ?
 C4 C3 H3 109.5 . . ?
 C13 C3 H3 109.5 . . ?
 C13 C3 C4 110.6(6) . . ?
 C2A C3A H3A 110.4 . . ?
 C2A C3A C4A 105.7(7) . . ?
 C4A C3A H3A 110.4 . . ?
 C13 C3A C2A 108.2(8) . . ?
 C13 C3A H3A 110.4 . . ?
 C13 C3A C4A 111.5(7) . . ?
 C3 C4 H4A 110.9 . . ?
 C3 C4 H4B 110.9 . . ?
 H4A C4 H4B 108.9 . . ?
 C5 C4 C3 104.4(6) . . ?
 C5 C4 H4A 110.9 . . ?
 C5 C4 H4B 110.9 . . ?
 C3A C4A H4AA 110.5 . . ?
 C3A C4A H4AB 110.5 . . ?
 C3A C4A C5A 106.1(6) . . ?
 H4AA C4A H4AB 108.7 . . ?
 C5A C4A H4AA 110.5 . . ?
 C5A C4A H4AB 110.5 . . ?
 C1 C5 H5A 110.6 . . ?
 C1 C5 H5B 110.6 . . ?
 C4 C5 C1 105.9(6) . . ?
 C4 C5 H5A 110.6 . . ?
 C4 C5 H5B 110.6 . . ?
 H5A C5 H5B 108.7 . . ?
 C1A C5A C4A 106.2(6) . . ?
 C1A C5A H5AA 110.5 . . ?
 C1A C5A H5AB 110.5 . . ?
 C4A C5A H5AA 110.5 . . ?
 C4A C5A H5AB 110.5 . . ?
 H5AA C5A H5AB 108.7 . . ?
 N1 C6 C1 108.5(5) . . ?
 N1 C6 C1A 117.6(4) . . ?
 N1 C6 H6A 110.0 . . ?
 N1 C6 H6B 110.0 . . ?
 C1 C6 H6A 110.0 . . ?
 C1 C6 H6B 110.0 . . ?
 H6A C6 H6B 108.4 . . ?
 C8 C7 N1 119.0(4) . . ?
 C8 C7 C12 120.0 . . ?
 C12 C7 N1 120.9(3) . . ?
 C8A C7 N1 119.5(9) . . ?
 C8A C7 C12A 126.0(13) . . ?
 C12A C7 N1 113.5(10) . . ?
 C7 C8 H8 120.0 . . ?
 C7 C8 C9 120.0 . . ?
 C9 C8 H8 120.0 . . ?
 C8 C9 H9 120.0 . . ?
 C8 C9 C10 120.0 . . ?
 C10 C9 H9 120.0 . . ?
 F1 C10 C9 123.1(12) . . ?
 F1 C10 C11 116.9(12) . . ?
 C11 C10 C9 120.0 . . ?
 C10 C11 H11 120.0 . . ?
 C10 C11 C12 120.0 . . ?
 C12 C11 H11 120.0 . . ?
 C7 C12 H12 120.0 . . ?
 C11 C12 C7 120.0 . . ?
 C11 C12 H12 120.0 . . ?
 C7 C8A H8A 119.5 . . ?
 C7 C8A C9A 121.0(14) . . ?
 C9A C8A H8A 119.5 . . ?
 C8A C9A H9A 123.8 . . ?
 C8A C9A C10A 112.4(17) . . ?
 C10A C9A H9A 123.8 . . ?
 C9A C10A F1A 109(2) . . ?
 C11A C10A F1A 123(2) . . ?
 C11A C10A C9A 127.1(16) . . ?
 C10A C11A H11A 121.7 . . ?
 C10A C11A C12A 116.7(14) . . ?
 C12A C11A H11A 121.7 . . ?
 C7 C12A C11A 115.7(14) . . ?
 C7 C12A H12A 122.1 . . ?
 C11A C12A H12A 122.1 . . ?
 N2 C13 C3 117.1(5) . . ?
 N2 C13 C3A 108.9(5) . . ?
 N2 C13 H13A 108.0 . . ?
 N2 C13 H13B 108.0 . . ?
 C3 C13 H13A 108.0 . . ?
 C3 C13 H13B 108.0 . . ?
 H13A C13 H13B 107.3 . . ?
 C15 C14 N2 118.0(11) . . ?
 C19 C14 N2 119.9(11) . . ?
 C19 C14 C15 122.0(8) . . ?
 N2 C14A C19A 118.9(16) . . ?
 N2 C14A C15A 120.8(16) . . ?
 C19A C14A C15A 120.0 . . ?
 C14A C19A H19A 120.0 . . ?
 C18A C19A C14A 120.0 . . ?
 C18A C19A H19A 120.0 . . ?
 C19A C18A H18A 120.0 . . ?
 C17A C18A C19A 120.0 . . ?
 C17A C18A H18A 120.0 . . ?
 F2A C17A C18A 120.5(16) . . ?
 F2A C17A C16A 119.4(16) . . ?
 C18A C17A C16A 120.0 . . ?
 C17A C16A H16A 120.0 . . ?
 C17A C16A C15A 120.0 . . ?
 C15A C16A H16A 120.0 . . ?
 C14A C15A H15A 120.0 . . ?
 C16A C15A C14A 120.0 . . ?
 C16A C15A H15A 120.0 . . ?
 C14 C15 H15 120.0 . . ?
 C16 C15 C14 120.0(8) . . ?
 C16 C15 H15 120.0 . . ?
 C15 C16 H16 121.4 . . ?
 C15 C16 C17 117.2(9) . . ?
 C17 C16 H16 121.4 . . ?
 F2 C17 C16 118.8(12) . . ?
 F2 C17 C18 118.1(11) . . ?
 C18 C17 C16 123.2(9) . . ?
 C17 C18 H18 120.1 . . ?
 C17 C18 C19 119.7(8) . . ?
 C19 C18 H18 120.1 . . ?
 C14 C19 H19 121.1 . . ?
 C18 C19 C14 117.9(8) . . ?
 C18 C19 H19 121.1 . . ?

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
 F1 C10 C11 C12 -179.6(10) . . . . ?
 F1A C10A C11A C12A 176(2) . . . . ?
 F2 C17 C18 C19 178.0(12) . . . . ?
 F2A C17A C16A C15A -177.6(19) . . . . ?
 N1 C7 C8 C9 175.3(5) . . . . ?
 N1 C7 C12 C11 -175.2(5) . . . . ?
 N1 C7 C8A C9A -174.4(19) . . . . ?
 N1 C7 C12A C11A 169.7(14) . . . . ?
 N2 C14 C15 C16 175.7(13) . . . . ?
 N2 C14 C19 C18 -176.0(16) . . . . ?
 N2 C14A C19A C18A 173(2) . . . . ?
 N2 C14A C15A C16A -173(2) . . . . ?
 C1 C2 C3 C4 -39.7(9) . . . . ?
 C1 C2 C3 C13 -159.8(7) . . . . ?
 C1A C2A C3A C4A 30.8(9) . . . . ?
 C1A C2A C3A C13 150.4(6) . . . . ?
 C2 C1 C5 C4 -4.1(9) . . . . ?
 C2 C1 C6 N1 153.5(5) . . . . ?
 C2 C3 C4 C5 36.2(9) . . . . ?
 C2 C3 C13 N2 -173.2(5) . . . . ?
 C2A C1A C5A C4A 35.1(8) . . . . ?
 C2A C1A C6 N1 -173.9(5) . . . . ?
 C2A C3A C4A C5A -9.0(9) . . . . ?
 C2A C3A C13 N2 151.7(5) . . . . ?
 C3 C4 C5 C1 -19.8(9) . . . . ?
 C3A C4A C5A C1A -16.7(9) . . . . ?
 C4 C3 C13 N2 71.4(9) . . . . ?
 C4A C3A C13 N2 -92.4(7) . . . . ?
 C5 C1 C2 C3 27.5(9) . . . . ?
 C5 C1 C6 N1 -91.1(7) . . . . ?
 C5A C1A C2A C3A -40.5(8) . . . . ?
 C5A C1A C6 N1 72.1(7) . . . . ?
 C6 N1 C7 C8 -101.6(5) . . . . ?
 C6 N1 C7 C12 73.7(5) . . . . ?
 C6 N1 C7 C8A -118.2(18) . . . . ?
 C6 N1 C7 C12A 72.7(10) . . . . ?
 C6 C1 C2 C3 145.8(7) . . . . ?
 C6 C1 C5 C4 -122.1(7) . . . . ?
 C6 C1A C2A C3A -159.9(7) . . . . ?
 C6 C1A C5A C4A 156.7(6) . . . . ?
 C7 N1 C6 C1 68.0(5) . . . . ?
 C7 N1 C6 C1A 46.5(5) . . . . ?
 C7 C8 C9 C10 0.0 . . . . ?
 C7 C8A C9A C10A 2(4) . . . . ?
 C8 C7 C12 C11 0.0 . . . . ?
 C8 C9 C10 F1 179.6(11) . . . . ?
 C8 C9 C10 C11 0.0 . . . . ?
 C9 C10 C11 C12 0.0 . . . . ?
 C10 C11 C12 C7 0.0 . . . . ?
 C12 C7 C8 C9 0.0 . . . . ?
 C8A C7 C12A C11A 1(2) . . . . ?
 C8A C9A C10A F1A 180(2) . . . . ?
 C8A C9A C10A C11A 8(4) . . . . ?
 C9A C10A C11A C12A -13(4) . . . . ?
 C10A C11A C12A C7 8(2) . . . . ?
 C12A C7 C8A C9A -7(3) . . . . ?
 C13 N2 C14 C15 -103.5(13) . . . . ?
 C13 N2 C14 C19 73.6(10) . . . . ?
 C13 N2 C14A C19A 67.3(14) . . . . ?
 C13 N2 C14A C15A -119.4(17) . . . . ?
 C13 C3 C4 C5 159.3(7) . . . . ?
 C13 C3A C4A C5A -126.3(8) . . . . ?
 C14 N2 C13 C3 48.9(9) . . . . ?
 C14 C15 C16 C17 0.5(19) . . . . ?
 C14A N2 C13 C3A 67.0(14) . . . . ?
 C14A C19A C18A C17A 0.0 . . . . ?
 C19A C14A C15A C16A 0.0 . . . . ?
 C19A C18A C17A F2A 177.5(19) . . . . ?
 C19A C18A C17A C16A 0.0 . . . . ?
 C18A C17A C16A C15A 0.0 . . . . ?
 C17A C16A C15A C14A 0.0 . . . . ?
 C15A C14A C19A C18A 0.0 . . . . ?
 C15 C14 C19 C18 1.0(13) . . . . ?
 C15 C16 C17 F2 -178.3(12) . . . . ?
 C15 C16 C17 C18 1(2) . . . . ?
 C16 C17 C18 C19 -1(2) . . . . ?
 C17 C18 C19 C14 0.1(15) . . . . ?
 C19 C14 C15 C16 -1.4(16) . . . . ?

_smtbx_masks_special_details       ?
loop_
  _smtbx_masks_void_nr
  _smtbx_masks_void_average_x
  _smtbx_masks_void_average_y
  _smtbx_masks_void_average_z
  _smtbx_masks_void_volume
  _smtbx_masks_void_count_electrons
  _smtbx_masks_void_content
 1 0.000 0.255 -0.867 197.0 62.0 '0.25 Dichloroethane'
 2 0.000 0.745 -0.382 197.0 62.0 '0.25 Dichloroethane'
 3 0.500 0.245 -0.403 197.0 62.0 '0.25 Dichloroethane'
 4 0.500 0.755 -0.971 197.0 62.0 '0.25 Dichloroethane'

_smtbx_masks_void_probe_radius     1.2
_smtbx_masks_void_truncation_radius  1.2
_olex2_submission_special_instructions  'No special instructions were received'
