data_251101wsh
_audit_creation_date               2025-11-03
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_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           'C14 H14 Br N O2'
_chemical_formula_sum              'C14 H14 Br N O2'
_chemical_formula_weight           308.17
_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        'orthorhombic'
_space_group_IT_number             19
_space_group_name_H-M_alt          'P 21 21 21'
_space_group_name_Hall             'P 2ac 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'

_cell_length_a                     5.71060(10)
_cell_length_b                     10.4678(2)
_cell_length_c                     21.2022(3)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       1267.41(4)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      9965
_cell_measurement_temperature      170.00
_cell_measurement_theta_max        68.69
_cell_measurement_theta_min        3.63
_shelx_estimated_absorpt_T_max     0.865
_shelx_estimated_absorpt_T_min     0.616
_exptl_absorpt_coefficient_mu      2.979
_exptl_absorpt_correction_T_max    0.7531
_exptl_absorpt_correction_T_min    0.5124
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1168 before and 0.0688 after correction.
The Ratio of minimum to maximum transmission is 0.6804.
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      1.615
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         prism
_exptl_crystal_F_000               624
_exptl_crystal_size_max            0.18
_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    0.0481
_diffrn_reflns_av_unetI/netI       0.0340
_diffrn_reflns_Laue_measured_fraction_full  0.996
_diffrn_reflns_Laue_measured_fraction_max  0.997
_diffrn_reflns_limit_h_max         7
_diffrn_reflns_limit_h_min         -7
_diffrn_reflns_limit_k_max         13
_diffrn_reflns_limit_k_min         -14
_diffrn_reflns_limit_l_max         26
_diffrn_reflns_limit_l_min         -29
_diffrn_reflns_number              18279
_diffrn_reflns_point_group_measured_fraction_full  0.996
_diffrn_reflns_point_group_measured_fraction_max  0.997
_diffrn_reflns_theta_full          53.594
_diffrn_reflns_theta_max           68.650
_diffrn_reflns_theta_min           3.627
_diffrn_ambient_temperature        170.00
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.996
_diffrn_measured_fraction_theta_max  0.997
_diffrn_measurement_device_type    'Bruker D8 Venture'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             GaK\a
_diffrn_radiation_wavelength       1.34139
_diffrn_source                     ?
_diffrn_source_current             3.57
_diffrn_source_power               0.2491146
_diffrn_source_voltage             69.78
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.719
_reflns_Friedel_fraction_full      0.996
_reflns_Friedel_fraction_max       0.997
_reflns_number_gt                  3500
_reflns_number_total               3549
_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 V8.41 (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.41 (?, 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  (Sheldrick, 2015)'
_refine_diff_density_max           0.360
_refine_diff_density_min           -0.244
_refine_diff_density_rms           0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1452 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     -0.005(6)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.035
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       165
_refine_ls_number_reflns           3549
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0203
_refine_ls_R_factor_gt             0.0201
_refine_ls_restrained_S_all        1.035
_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)+(0.0274P)²+0.1191P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0534
_refine_ls_wR_factor_ref           0.0535
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C9(H9), C11(H11), C12(H12)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.86366(4) 0.43576(2) 0.52720(2) 0.02834(7) Uani 1 1 d . . . . .
 O1 O 0.6588(2) 0.34622(12) 0.82207(7) 0.0258(3) Uani 1 1 d . . . . .
 O2 O 0.0998(2) 0.31975(13) 0.77512(6) 0.0257(3) Uani 1 1 d . . . . .
 H2 H -0.030961 0.333493 0.791969 0.039 Uiso 1 1 calc R U . . .
 N1 N 0.3895(3) 0.37201(14) 0.89866(7) 0.0223(3) Uani 1 1 d . . . . .
 C1 C 0.3618(3) 0.50516(13) 0.80296(7) 0.0171(3) Uani 1 1 d . . . . .
 C2 C 0.1960(3) 0.43648(17) 0.75379(8) 0.0193(3) Uani 1 1 d . . . . .
 H2A H 0.064756 0.495757 0.742885 0.023 Uiso 1 1 calc R U . . .
 C3 C 0.4824(3) 0.40162(15) 0.84197(8) 0.0182(3) Uani 1 1 d . . . . .
 C4 C 0.1780(3) 0.42901(19) 0.92471(8) 0.0267(3) Uani 1 1 d . . . . .
 H4A H 0.194948 0.436348 0.971039 0.032 Uiso 1 1 calc R U . . .
 H4B H 0.043404 0.372040 0.916065 0.032 Uiso 1 1 calc R U . . .
 C5 C 0.1284(4) 0.55827(18) 0.89778(9) 0.0281(3) Uani 1 1 d . . . . .
 H5 H 0.029827 0.615506 0.920232 0.034 Uiso 1 1 calc R U . . .
 C6 C 0.2195(3) 0.59426(16) 0.84318(9) 0.0239(3) Uani 1 1 d . . . . .
 H6 H 0.194047 0.679206 0.828971 0.029 Uiso 1 1 calc R U . . .
 C7 C 0.5444(3) 0.57433(15) 0.76081(7) 0.0195(3) Uani 1 1 d . . . . .
 H7A H 0.497802 0.664116 0.753201 0.023 Uiso 1 1 calc R U . . .
 H7B H 0.701160 0.573154 0.780716 0.023 Uiso 1 1 calc R U . . .
 C8 C 0.5446(3) 0.49906(14) 0.70002(7) 0.0172(3) Uani 1 1 d . . . . .
 C9 C 0.7033(3) 0.50476(15) 0.65029(8) 0.0192(3) Uani 1 1 d . . . . .
 H9 H 0.837649 0.558113 0.652126 0.023 Uiso 1 1 calc R U . . .
 C10 C 0.6570(3) 0.42903(15) 0.59767(7) 0.0200(3) Uani 1 1 d . . . . .
 C11 C 0.4633(4) 0.34963(17) 0.59346(8) 0.0238(3) Uani 1 1 d . . . . .
 H11 H 0.437941 0.299037 0.556896 0.029 Uiso 1 1 calc R U . . .
 C12 C 0.3058(3) 0.34523(17) 0.64388(8) 0.0233(3) Uani 1 1 d . . . . .
 H12 H 0.171523 0.291798 0.642113 0.028 Uiso 1 1 calc R U . . .
 C13 C 0.3491(3) 0.42024(15) 0.69655(7) 0.0187(3) Uani 1 1 d . . . . .
 C14 C 0.4889(4) 0.26664(18) 0.93497(9) 0.0294(4) Uani 1 1 d . . . . .
 H14A H 0.367231 0.202771 0.943184 0.044 Uiso 1 1 calc R U . . .
 H14B H 0.549640 0.299135 0.975120 0.044 Uiso 1 1 calc R U . . .
 H14C H 0.616678 0.227292 0.910987 0.044 Uiso 1 1 calc R U . . .


_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 1.9051(16) . ?
 O1 C3 1.237(2) . ?
 O2 H2 0.8400 . ?
 O2 C2 1.414(2) . ?
 N1 C3 1.350(2) . ?
 N1 C4 1.456(2) . ?
 N1 C14 1.460(2) . ?
 C1 C2 1.581(2) . ?
 C1 C3 1.527(2) . ?
 C1 C6 1.502(2) . ?
 C1 C7 1.552(2) . ?
 C2 H2A 1.0000 . ?
 C2 C13 1.505(2) . ?
 C4 H4A 0.9900 . ?
 C4 H4B 0.9900 . ?
 C4 C5 1.496(3) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.324(3) . ?
 C6 H6 0.9500 . ?
 C7 H7A 0.9900 . ?
 C7 H7B 0.9900 . ?
 C7 C8 1.511(2) . ?
 C8 C9 1.392(2) . ?
 C8 C13 1.390(2) . ?
 C9 H9 0.9500 . ?
 C9 C10 1.394(2) . ?
 C10 C11 1.387(2) . ?
 C11 H11 0.9500 . ?
 C11 C12 1.397(3) . ?
 C12 H12 0.9500 . ?
 C12 C13 1.387(2) . ?
 C14 H14A 0.9800 . ?
 C14 H14B 0.9800 . ?
 C14 H14C 0.9800 . ?

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
 C2 O2 H2 109.5 . . ?
 C3 N1 C4 124.71(15) . . ?
 C3 N1 C14 119.36(16) . . ?
 C4 N1 C14 115.60(15) . . ?
 C3 C1 C2 107.72(12) . . ?
 C3 C1 C7 109.87(14) . . ?
 C6 C1 C2 109.43(15) . . ?
 C6 C1 C3 112.15(13) . . ?
 C6 C1 C7 113.60(13) . . ?
 C7 C1 C2 103.57(12) . . ?
 O2 C2 C1 114.49(13) . . ?
 O2 C2 H2A 108.6 . . ?
 O2 C2 C13 112.71(14) . . ?
 C1 C2 H2A 108.6 . . ?
 C13 C2 C1 103.60(13) . . ?
 C13 C2 H2A 108.6 . . ?
 O1 C3 N1 121.07(16) . . ?
 O1 C3 C1 121.02(15) . . ?
 N1 C3 C1 117.91(15) . . ?
 N1 C4 H4A 109.1 . . ?
 N1 C4 H4B 109.1 . . ?
 N1 C4 C5 112.52(15) . . ?
 H4A C4 H4B 107.8 . . ?
 C5 C4 H4A 109.1 . . ?
 C5 C4 H4B 109.1 . . ?
 C4 C5 H5 119.4 . . ?
 C6 C5 C4 121.12(16) . . ?
 C6 C5 H5 119.4 . . ?
 C1 C6 H6 118.9 . . ?
 C5 C6 C1 122.15(16) . . ?
 C5 C6 H6 118.9 . . ?
 C1 C7 H7A 110.9 . . ?
 C1 C7 H7B 110.9 . . ?
 H7A C7 H7B 108.9 . . ?
 C8 C7 C1 104.39(13) . . ?
 C8 C7 H7A 110.9 . . ?
 C8 C7 H7B 110.9 . . ?
 C9 C8 C7 128.67(15) . . ?
 C13 C8 C7 110.73(14) . . ?
 C13 C8 C9 120.55(15) . . ?
 C8 C9 H9 121.3 . . ?
 C8 C9 C10 117.32(16) . . ?
 C10 C9 H9 121.3 . . ?
 C9 C10 Br1 119.30(13) . . ?
 C11 C10 Br1 117.78(12) . . ?
 C11 C10 C9 122.91(16) . . ?
 C10 C11 H11 120.5 . . ?
 C10 C11 C12 118.94(15) . . ?
 C12 C11 H11 120.5 . . ?
 C11 C12 H12 120.6 . . ?
 C13 C12 C11 118.86(16) . . ?
 C13 C12 H12 120.6 . . ?
 C8 C13 C2 110.90(14) . . ?
 C12 C13 C2 127.56(16) . . ?
 C12 C13 C8 121.42(16) . . ?
 N1 C14 H14A 109.5 . . ?
 N1 C14 H14B 109.5 . . ?
 N1 C14 H14C 109.5 . . ?
 H14A C14 H14B 109.5 . . ?
 H14A C14 H14C 109.5 . . ?
 H14B C14 H14C 109.5 . . ?

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 -178.47(13) . . . . ?
 O2 C2 C13 C8 -141.05(14) . . . . ?
 O2 C2 C13 C12 42.9(2) . . . . ?
 N1 C4 C5 C6 20.8(3) . . . . ?
 C1 C2 C13 C8 -16.74(17) . . . . ?
 C1 C2 C13 C12 167.18(16) . . . . ?
 C1 C7 C8 C9 -167.46(16) . . . . ?
 C1 C7 C8 C13 15.34(17) . . . . ?
 C2 C1 C3 O1 82.45(19) . . . . ?
 C2 C1 C3 N1 -97.18(16) . . . . ?
 C2 C1 C6 C5 92.5(2) . . . . ?
 C2 C1 C7 C8 -24.40(16) . . . . ?
 C3 N1 C4 C5 -24.4(2) . . . . ?
 C3 C1 C2 O2 31.71(19) . . . . ?
 C3 C1 C2 C13 -91.42(15) . . . . ?
 C3 C1 C6 C5 -27.0(3) . . . . ?
 C3 C1 C7 C8 90.44(15) . . . . ?
 C4 N1 C3 O1 -177.70(16) . . . . ?
 C4 N1 C3 C1 1.9(2) . . . . ?
 C4 C5 C6 C1 4.7(3) . . . . ?
 C6 C1 C2 O2 -90.45(16) . . . . ?
 C6 C1 C2 C13 146.41(13) . . . . ?
 C6 C1 C3 O1 -157.08(16) . . . . ?
 C6 C1 C3 N1 23.3(2) . . . . ?
 C6 C1 C7 C8 -143.02(15) . . . . ?
 C7 C1 C2 O2 148.08(13) . . . . ?
 C7 C1 C2 C13 24.95(16) . . . . ?
 C7 C1 C3 O1 -29.7(2) . . . . ?
 C7 C1 C3 N1 150.65(14) . . . . ?
 C7 C1 C6 C5 -152.31(19) . . . . ?
 C7 C8 C9 C10 -176.85(16) . . . . ?
 C7 C8 C13 C2 1.13(18) . . . . ?
 C7 C8 C13 C12 177.49(15) . . . . ?
 C8 C9 C10 Br1 178.49(12) . . . . ?
 C8 C9 C10 C11 -0.3(2) . . . . ?
 C9 C8 C13 C2 -176.34(14) . . . . ?
 C9 C8 C13 C12 0.0(2) . . . . ?
 C9 C10 C11 C12 0.3(3) . . . . ?
 C10 C11 C12 C13 -0.2(3) . . . . ?
 C11 C12 C13 C2 175.72(16) . . . . ?
 C11 C12 C13 C8 0.0(3) . . . . ?
 C13 C8 C9 C10 0.1(2) . . . . ?
 C14 N1 C3 O1 -4.5(3) . . . . ?
 C14 N1 C3 C1 175.16(15) . . . . ?
 C14 N1 C4 C5 162.14(16) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
