data_240827wsh
_audit_creation_date               2025-10-11
_audit_creation_method
;
Olex2 1.5
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_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 H12 Br N O2'
_chemical_formula_sum              'C14 H12 Br N O2'
_chemical_formula_weight           306.16
_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                     7.13760(10)
_cell_length_b                     7.65440(10)
_cell_length_c                     22.3119(4)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       1218.99(3)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      9223
_cell_measurement_temperature      170.00
_cell_measurement_theta_max        54.90
_cell_measurement_theta_min        3.45
_shelx_estimated_absorpt_T_max     0.864
_shelx_estimated_absorpt_T_min     0.629
_exptl_absorpt_coefficient_mu      3.001
_exptl_absorpt_correction_T_max    0.7508
_exptl_absorpt_correction_T_min    0.5422
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1504 before and 0.0741 after correction.
The Ratio of minimum to maximum transmission is 0.7222.
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      1.668
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               616
_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    0.0544
_diffrn_reflns_av_unetI/netI       0.0371
_diffrn_reflns_Laue_measured_fraction_full  0.992
_diffrn_reflns_Laue_measured_fraction_max  0.989
_diffrn_reflns_limit_h_max         8
_diffrn_reflns_limit_h_min         -8
_diffrn_reflns_limit_k_max         9
_diffrn_reflns_limit_k_min         -9
_diffrn_reflns_limit_l_max         27
_diffrn_reflns_limit_l_min         -25
_diffrn_reflns_number              11484
_diffrn_reflns_point_group_measured_fraction_full  0.992
_diffrn_reflns_point_group_measured_fraction_max  0.988
_diffrn_reflns_theta_full          53.594
_diffrn_reflns_theta_max           54.947
_diffrn_reflns_theta_min           3.447
_diffrn_ambient_temperature        170.00
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.992
_diffrn_measured_fraction_theta_max  0.989
_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           0.686
_reflns_Friedel_fraction_full      0.993
_reflns_Friedel_fraction_max       0.985
_reflns_number_gt                  2174
_reflns_number_total               2298
_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           0.337
_refine_diff_density_min           -0.766
_refine_diff_density_rms           0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 863 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.024(13)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.053
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       164
_refine_ls_number_reflns           2298
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0298
_refine_ls_R_factor_gt             0.0260
_refine_ls_restrained_S_all        1.053
_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)+(0.0344P)²+0.4591P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0649
_refine_ls_wR_factor_ref           0.0672
_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
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_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 0.72978(6) 0.78142(5) 0.62567(2) 0.03020(14) Uani 1 1 d . . . . .
 O1 O 0.7300(4) 0.5719(3) 0.32093(9) 0.0238(5) Uani 1 1 d . . . . .
 O2 O 0.9938(3) 0.2221(4) 0.36100(11) 0.0283(6) Uani 1 1 d . . . . .
 N1 N 0.7726(4) 0.0954(3) 0.30332(11) 0.0194(6) Uani 1 1 d . . . . .
 C1 C 0.6800(5) 0.3076(4) 0.38150(14) 0.0176(6) Uani 1 1 d . . . . .
 C2 C 0.7177(4) 0.5059(3) 0.36991(13) 0.0170(7) Uani 1 1 d . . . . .
 C3 C 0.7262(5) 0.5934(4) 0.42863(13) 0.0179(7) Uani 1 1 d . . . . .
 C4 C 0.7155(5) 0.4709(4) 0.47470(14) 0.0176(7) Uani 1 1 d . . . . .
 C5 C 0.7068(5) 0.2869(4) 0.45033(13) 0.0194(7) Uani 1 1 d . . . . .
 H5A H 0.600406 0.222237 0.468147 0.023 Uiso 1 1 calc R U . . .
 H5B H 0.824214 0.223093 0.459250 0.023 Uiso 1 1 calc R U . . .
 C6 C 0.7148(5) 0.5230(4) 0.53416(14) 0.0186(7) Uani 1 1 d . . . . .
 H6 H 0.704815 0.440767 0.565874 0.022 Uiso 1 1 calc R U . . .
 C7 C 0.7294(5) 0.7012(4) 0.54530(13) 0.0191(6) Uani 1 1 d . . . . .
 C8 C 0.7411(5) 0.8257(4) 0.49990(14) 0.0233(7) Uani 1 1 d . . . . .
 H8 H 0.750647 0.946262 0.509507 0.028 Uiso 1 1 calc R U . . .
 C9 C 0.7388(5) 0.7720(4) 0.44064(14) 0.0216(7) Uani 1 1 d . . . . .
 H9 H 0.745680 0.854684 0.408955 0.026 Uiso 1 1 calc R U . . .
 C10 C 0.8276(5) 0.2037(4) 0.34716(14) 0.0186(7) Uani 1 1 d . . . . .
 C11 C 0.9124(6) -0.0041(5) 0.26985(17) 0.0275(9) Uani 1 1 d . . . . .
 H11A H 1.014775 0.073719 0.257781 0.041 Uiso 1 1 calc R U . . .
 H11B H 0.854226 -0.054845 0.234087 0.041 Uiso 1 1 calc R U . . .
 H11C H 0.962138 -0.097739 0.295212 0.041 Uiso 1 1 calc R U . . .
 C12 C 0.5793(5) 0.0610(5) 0.28493(17) 0.0277(8) Uani 1 1 d . . . . .
 H12A H 0.553705 -0.065514 0.289156 0.033 Uiso 1 1 calc R U . . .
 H12B H 0.565440 0.091440 0.242029 0.033 Uiso 1 1 calc R U . . .
 C13 C 0.4378(5) 0.1599(5) 0.32010(16) 0.0229(8) Uani 1 1 d . . . . .
 H13 H 0.309145 0.142978 0.310813 0.027 Uiso 1 1 calc R U . . .
 C14 C 0.4806(5) 0.2698(4) 0.36341(15) 0.0207(7) Uani 1 1 d . . . . .
 H14 H 0.381961 0.327427 0.384064 0.025 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 C7 1.895(3) . ?
 O1 C2 1.207(4) . ?
 O2 C10 1.234(4) . ?
 N1 C10 1.341(4) . ?
 N1 C11 1.461(4) . ?
 N1 C12 1.464(5) . ?
 C1 C2 1.563(4) . ?
 C1 C5 1.556(4) . ?
 C1 C10 1.526(4) . ?
 C1 C14 1.508(5) . ?
 C2 C3 1.473(4) . ?
 C3 C4 1.393(4) . ?
 C3 C9 1.396(4) . ?
 C4 C5 1.511(4) . ?
 C4 C6 1.385(4) . ?
 C5 H5A 0.9900 . ?
 C5 H5B 0.9900 . ?
 C6 H6 0.9500 . ?
 C6 C7 1.390(4) . ?
 C7 C8 1.393(4) . ?
 C8 H8 0.9500 . ?
 C8 C9 1.384(5) . ?
 C9 H9 0.9500 . ?
 C11 H11A 0.9800 . ?
 C11 H11B 0.9800 . ?
 C11 H11C 0.9800 . ?
 C12 H12A 0.9900 . ?
 C12 H12B 0.9900 . ?
 C12 C13 1.487(5) . ?
 C13 H13 0.9500 . ?
 C13 C14 1.317(5) . ?
 C14 H14 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
 C10 N1 C11 119.7(3) . . ?
 C10 N1 C12 126.3(3) . . ?
 C11 N1 C12 114.0(3) . . ?
 C5 C1 C2 104.0(2) . . ?
 C10 C1 C2 107.7(3) . . ?
 C10 C1 C5 110.9(3) . . ?
 C14 C1 C2 107.8(3) . . ?
 C14 C1 C5 111.2(3) . . ?
 C14 C1 C10 114.7(3) . . ?
 O1 C2 C1 124.6(3) . . ?
 O1 C2 C3 127.8(3) . . ?
 C3 C2 C1 107.5(2) . . ?
 C4 C3 C2 110.4(3) . . ?
 C4 C3 C9 121.4(3) . . ?
 C9 C3 C2 128.2(3) . . ?
 C3 C4 C5 111.3(3) . . ?
 C6 C4 C3 120.9(3) . . ?
 C6 C4 C5 127.8(3) . . ?
 C1 C5 H5A 110.7 . . ?
 C1 C5 H5B 110.7 . . ?
 C4 C5 C1 105.4(2) . . ?
 C4 C5 H5A 110.7 . . ?
 C4 C5 H5B 110.7 . . ?
 H5A C5 H5B 108.8 . . ?
 C4 C6 H6 121.5 . . ?
 C4 C6 C7 117.0(3) . . ?
 C7 C6 H6 121.5 . . ?
 C6 C7 Br1 119.1(2) . . ?
 C6 C7 C8 123.0(3) . . ?
 C8 C7 Br1 117.8(2) . . ?
 C7 C8 H8 120.3 . . ?
 C9 C8 C7 119.4(3) . . ?
 C9 C8 H8 120.3 . . ?
 C3 C9 H9 120.8 . . ?
 C8 C9 C3 118.3(3) . . ?
 C8 C9 H9 120.8 . . ?
 O2 C10 N1 122.3(3) . . ?
 O2 C10 C1 118.6(3) . . ?
 N1 C10 C1 119.1(3) . . ?
 N1 C11 H11A 109.5 . . ?
 N1 C11 H11B 109.5 . . ?
 N1 C11 H11C 109.5 . . ?
 H11A C11 H11B 109.5 . . ?
 H11A C11 H11C 109.5 . . ?
 H11B C11 H11C 109.5 . . ?
 N1 C12 H12A 108.8 . . ?
 N1 C12 H12B 108.8 . . ?
 N1 C12 C13 113.6(3) . . ?
 H12A C12 H12B 107.7 . . ?
 C13 C12 H12A 108.8 . . ?
 C13 C12 H12B 108.8 . . ?
 C12 C13 H13 118.1 . . ?
 C14 C13 C12 123.7(3) . . ?
 C14 C13 H13 118.1 . . ?
 C1 C14 H14 118.7 . . ?
 C13 C14 C1 122.6(3) . . ?
 C13 C14 H14 118.7 . . ?

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 C7 C8 C9 -179.2(3) . . . . ?
 O1 C2 C3 C4 -177.1(3) . . . . ?
 O1 C2 C3 C9 4.2(6) . . . . ?
 N1 C12 C13 C14 0.6(5) . . . . ?
 C1 C2 C3 C4 5.5(4) . . . . ?
 C1 C2 C3 C9 -173.2(4) . . . . ?
 C2 C1 C5 C4 11.6(3) . . . . ?
 C2 C1 C10 O2 62.9(4) . . . . ?
 C2 C1 C10 N1 -117.4(3) . . . . ?
 C2 C1 C14 C13 117.8(3) . . . . ?
 C2 C3 C4 C5 2.4(4) . . . . ?
 C2 C3 C4 C6 -178.0(3) . . . . ?
 C2 C3 C9 C8 178.7(3) . . . . ?
 C3 C4 C5 C1 -9.1(4) . . . . ?
 C3 C4 C6 C7 -1.4(5) . . . . ?
 C4 C3 C9 C8 0.2(6) . . . . ?
 C4 C6 C7 Br1 -179.9(2) . . . . ?
 C4 C6 C7 C8 1.1(5) . . . . ?
 C5 C1 C2 O1 171.9(3) . . . . ?
 C5 C1 C2 C3 -10.6(3) . . . . ?
 C5 C1 C10 O2 -50.2(4) . . . . ?
 C5 C1 C10 N1 129.5(3) . . . . ?
 C5 C1 C14 C13 -128.9(3) . . . . ?
 C5 C4 C6 C7 178.2(3) . . . . ?
 C6 C4 C5 C1 171.2(3) . . . . ?
 C6 C7 C8 C9 -0.1(5) . . . . ?
 C7 C8 C9 C3 -0.5(5) . . . . ?
 C9 C3 C4 C5 -178.9(3) . . . . ?
 C9 C3 C4 C6 0.8(5) . . . . ?
 C10 N1 C12 C13 0.0(5) . . . . ?
 C10 C1 C2 O1 54.1(4) . . . . ?
 C10 C1 C2 C3 -128.4(3) . . . . ?
 C10 C1 C5 C4 127.1(3) . . . . ?
 C10 C1 C14 C13 -2.1(5) . . . . ?
 C11 N1 C10 O2 -0.7(5) . . . . ?
 C11 N1 C10 C1 179.6(3) . . . . ?
 C11 N1 C12 C13 178.8(3) . . . . ?
 C12 N1 C10 O2 178.1(3) . . . . ?
 C12 N1 C10 C1 -1.6(5) . . . . ?
 C12 C13 C14 C1 0.5(5) . . . . ?
 C14 C1 C2 O1 -70.1(4) . . . . ?
 C14 C1 C2 C3 107.4(3) . . . . ?
 C14 C1 C5 C4 -104.1(3) . . . . ?
 C14 C1 C10 O2 -177.1(3) . . . . ?
 C14 C1 C10 N1 2.6(4) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
