#------------------------------------------------------------------------------
#$Date: 2025-03-04 20:32:55 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298037 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/41/7134183.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7134183
loop_
_publ_author_name
'Fang, Yi-Jun'
'Wu, Xiao-Bao'
'Wang, Qi-Ming'
'Xie, Zu-Kui'
'Yao, Chuan-Zhi'
'Jiang, Hua-Jie'
'Yu, Jie'
_publ_section_title
;
 High-performance anionic stereogenic-at-cobalt(III) complex/halide
 salts/oxone catalytic system for enantioselective halocyclization of
 olefins.
;
_journal_issue                   13
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2814
_journal_page_last               2817
_journal_paper_doi               10.1039/d4cc06610c
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C24 H24 Br N O2 S'
_chemical_formula_sum            'C24 H24 Br N O2 S'
_chemical_formula_weight         470.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-08-08 deposited with the CCDC.	2025-01-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8681(2)
_cell_length_b                   10.6446(2)
_cell_length_c                   21.1836(4)
_cell_measurement_reflns_used    9869
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      54.96
_cell_measurement_theta_min      3.63
_cell_volume                     2225.17(7)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_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_reflns_av_R_equivalents  0.0871
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            23732
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.978
_diffrn_reflns_theta_min         3.631
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.397
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.2054 before and 0.0980 after correction. The Ratio of minimum to maximum transmission is 0.5800. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.774
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 1525 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.021(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4220
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0520P)²+0.0224P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0966
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3884
_reflns_number_total             4220
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc06610c2.cif
_cod_data_source_block           210831fyj_2_0m
_cod_depositor_comments
'Adding full bibliography for 7134183--7134186.cif.'
_cod_database_code               7134183
_shelx_shelxl_version_number     2016/6
_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.
;
_shelx_estimated_absorpt_t_max   0.890
_shelx_estimated_absorpt_t_min   0.831
_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 Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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'
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 0.44991(5) 0.66174(4) 0.43687(2) 0.05860(17) Uani 1 1 d . . . . .
S1 S 0.52746(10) 0.74070(8) 0.63030(4) 0.0447(2) Uani 1 1 d . . . . .
O1 O 0.6478(3) 0.6742(3) 0.64650(14) 0.0590(7) Uani 1 1 d . . . . .
O2 O 0.5359(3) 0.8556(2) 0.59512(13) 0.0601(7) Uani 1 1 d . . . . .
N1 N 0.4363(3) 0.6450(3) 0.58863(13) 0.0410(7) Uani 1 1 d . . . . .
C1 C 0.3116(4) 0.6868(3) 0.55638(15) 0.0385(7) Uani 1 1 d . . . . .
H1 H 0.260251 0.741607 0.584874 0.046 Uiso 1 1 calc R . . . .
C2 C 0.2325(4) 0.5636(3) 0.54694(17) 0.0432(8) Uani 1 1 d . . . . .
H2A H 0.135828 0.578157 0.550901 0.052 Uiso 1 1 calc R . . . .
H2B H 0.250575 0.528672 0.505493 0.052 Uiso 1 1 calc R . . . .
C3 C 0.2820(4) 0.4738(3) 0.59882(16) 0.0392(8) Uani 1 1 d . . . . .
C4 C 0.4325(4) 0.5093(3) 0.60282(17) 0.0412(8) Uani 1 1 d . . . . .
H4A H 0.468018 0.492711 0.644696 0.049 Uiso 1 1 calc R . . . .
H4B H 0.485245 0.462291 0.572230 0.049 Uiso 1 1 calc R . . . .
C5 C 0.3384(4) 0.7568(4) 0.49505(17) 0.0474(9) Uani 1 1 d . . . . .
H5A H 0.383124 0.835712 0.504551 0.057 Uiso 1 1 calc R . . . .
H5B H 0.252602 0.775961 0.474929 0.057 Uiso 1 1 calc R . . . .
C6 C 0.2602(4) 0.3364(3) 0.57935(16) 0.0439(8) Uani 1 1 d . . . . .
C7 C 0.1325(5) 0.2972(4) 0.5613(2) 0.0551(10) Uani 1 1 d . . . . .
H7 H 0.061838 0.354912 0.560032 0.066 Uiso 1 1 calc R . . . .
C8 C 0.1081(5) 0.1728(4) 0.5452(2) 0.0674(12) Uani 1 1 d . . . . .
H8 H 0.021263 0.147398 0.533913 0.081 Uiso 1 1 calc R . . . .
C9 C 0.2119(6) 0.0879(4) 0.5458(2) 0.0700(14) Uani 1 1 d . . . . .
H9 H 0.196052 0.004847 0.534335 0.084 Uiso 1 1 calc R . . . .
C10 C 0.3386(5) 0.1249(4) 0.5631(3) 0.0694(13) Uani 1 1 d . . . . .
H10 H 0.409030 0.066842 0.563713 0.083 Uiso 1 1 calc R . . . .
C11 C 0.3633(5) 0.2488(4) 0.5799(2) 0.0596(11) Uani 1 1 d . . . . .
H11 H 0.450189 0.273086 0.591692 0.072 Uiso 1 1 calc R . . . .
C12 C 0.2111(4) 0.4932(3) 0.66315(16) 0.0408(8) Uani 1 1 d . . . . .
C13 C 0.2434(4) 0.4141(4) 0.71324(19) 0.0529(10) Uani 1 1 d . . . . .
H13 H 0.308725 0.352063 0.707832 0.063 Uiso 1 1 calc R . . . .
C14 C 0.1796(5) 0.4266(5) 0.7707(2) 0.0658(12) Uani 1 1 d . . . . .
H14 H 0.200894 0.371989 0.803530 0.079 Uiso 1 1 calc R . . . .
C15 C 0.0847(5) 0.5191(5) 0.7799(2) 0.0677(13) Uani 1 1 d . . . . .
H15 H 0.042383 0.527232 0.818936 0.081 Uiso 1 1 calc R . . . .
C16 C 0.0528(6) 0.5984(5) 0.7324(2) 0.0665(12) Uani 1 1 d . . . . .
H16 H -0.011183 0.661271 0.738755 0.080 Uiso 1 1 calc R . . . .
C17 C 0.1162(4) 0.5859(4) 0.6737(2) 0.0544(10) Uani 1 1 d . . . . .
H17 H 0.094021 0.641019 0.641226 0.065 Uiso 1 1 calc R . . . .
C18 C 0.4383(4) 0.7732(4) 0.70048(17) 0.0482(9) Uani 1 1 d . . . . .
C19 C 0.4448(5) 0.6894(5) 0.74954(18) 0.0638(11) Uani 1 1 d . . . . .
H19 H 0.499203 0.618285 0.746850 0.077 Uiso 1 1 calc R . . . .
C20 C 0.3681(6) 0.7131(7) 0.8037(2) 0.0825(18) Uani 1 1 d . . . . .
H20 H 0.369983 0.656264 0.836994 0.099 Uiso 1 1 calc R . . . .
C21 C 0.2889(6) 0.8206(8) 0.8083(3) 0.092(2) Uani 1 1 d . . . . .
C22 C 0.2859(6) 0.9016(6) 0.7588(3) 0.0866(18) Uani 1 1 d . . . . .
H22 H 0.233351 0.973964 0.761562 0.104 Uiso 1 1 calc R . . . .
C23 C 0.3587(5) 0.8791(5) 0.7048(2) 0.0690(13) Uani 1 1 d . . . . .
H23 H 0.354232 0.935102 0.671143 0.083 Uiso 1 1 calc R . . . .
C24 C 0.2043(9) 0.8412(10) 0.8680(3) 0.148(4) Uani 1 1 d . . . . .
H24A H 0.218508 0.925019 0.883309 0.222 Uiso 1 1 calc GR . . . .
H24B H 0.231326 0.781899 0.899708 0.222 Uiso 1 1 calc GR . . . .
H24C H 0.110127 0.829548 0.858286 0.222 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 -0.9502 1.0410 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2924 0.4247 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O1 S1 O2 120.05(19) . . ?
O1 S1 N1 106.35(16) . . ?
O1 S1 C18 108.08(19) . . ?
O2 S1 N1 106.56(16) . . ?
O2 S1 C18 107.46(19) . . ?
N1 S1 C18 107.82(17) . . ?
C1 N1 S1 121.7(2) . . ?
C4 N1 S1 121.2(2) . . ?
C4 N1 C1 111.6(3) . . ?
N1 C1 H1 109.0 . . ?
N1 C1 C2 103.0(3) . . ?
N1 C1 C5 113.4(3) . . ?
C2 C1 H1 109.0 . . ?
C5 C1 H1 109.0 . . ?
C5 C1 C2 113.2(3) . . ?
C1 C2 H2A 110.5 . . ?
C1 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
C3 C2 C1 106.0(3) . . ?
C3 C2 H2A 110.5 . . ?
C3 C2 H2B 110.5 . . ?
C2 C3 C12 113.8(3) . . ?
C4 C3 C2 101.2(3) . . ?
C4 C3 C12 110.9(3) . . ?
C6 C3 C2 110.8(3) . . ?
C6 C3 C4 112.7(3) . . ?
C6 C3 C12 107.5(3) . . ?
N1 C4 C3 104.8(3) . . ?
N1 C4 H4A 110.8 . . ?
N1 C4 H4B 110.8 . . ?
C3 C4 H4A 110.8 . . ?
C3 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
Br1 C5 H5A 109.0 . . ?
Br1 C5 H5B 109.0 . . ?
C1 C5 Br1 112.8(3) . . ?
C1 C5 H5A 109.0 . . ?
C1 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 C3 119.4(3) . . ?
C7 C6 C11 118.1(4) . . ?
C11 C6 C3 122.5(4) . . ?
C6 C7 H7 119.5 . . ?
C6 C7 C8 121.0(4) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 119.9(5) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(4) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.3(4) . . ?
C11 C10 H10 119.8 . . ?
C6 C11 C10 120.7(4) . . ?
C6 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C3 119.2(3) . . ?
C17 C12 C3 123.1(3) . . ?
C17 C12 C13 117.7(4) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.7(4) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(4) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.1(4) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 119.9(4) . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 121.0(4) . . ?
C12 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C19 C18 S1 119.3(4) . . ?
C19 C18 C23 120.6(4) . . ?
C23 C18 S1 120.1(3) . . ?
C18 C19 H19 120.7 . . ?
C18 C19 C20 118.7(5) . . ?
C20 C19 H19 120.7 . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.7(5) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 C24 118.9(8) . . ?
C22 C21 C20 118.8(5) . . ?
C22 C21 C24 122.3(8) . . ?
C21 C22 H22 119.3 . . ?
C21 C22 C23 121.4(6) . . ?
C23 C22 H22 119.3 . . ?
C18 C23 H23 120.1 . . ?
C22 C23 C18 119.8(5) . . ?
C22 C23 H23 120.1 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
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 C5 1.937(4) . ?
S1 O1 1.425(3) . ?
S1 O2 1.434(3) . ?
S1 N1 1.620(3) . ?
S1 C18 1.762(4) . ?
N1 C1 1.477(5) . ?
N1 C4 1.476(4) . ?
C1 H1 0.9800 . ?
C1 C2 1.540(5) . ?
C1 C5 1.521(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.536(5) . ?
C3 C4 1.535(5) . ?
C3 C6 1.535(5) . ?
C3 C12 1.546(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.381(6) . ?
C6 C11 1.380(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.388(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.366(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.361(8) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.392(5) . ?
C12 C17 1.378(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.372(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.351(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.399(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.371(6) . ?
C18 C23 1.377(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.397(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.389(9) . ?
C21 C22 1.358(9) . ?
C21 C24 1.531(8) . ?
C22 H22 0.9300 . ?
C22 C23 1.373(7) . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
