#------------------------------------------------------------------------------
#$Date: 2022-06-25 03:28:54 +0300 (Sat, 25 Jun 2022) $
#$Revision: 276265 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/87/7158737.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_7158737
loop_
_publ_author_name
'Jin, Lvnan'
'Zhou, Xuan'
'Zhao, Yunbo'
'Guo, Jing'
'Stephan, Douglas W.'
_publ_section_title
;
 Catalyst-dependent chemoselective insertion of diazoalkanes into
 N-HΧ-HΟ-HΧ-O bonds of 2-hydroxybenzothiazoles
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01048H
_journal_year                    2022
_chemical_formula_moiety         'C16 H12 Br N O3 S'
_chemical_formula_sum            'C16 H12 Br N O3 S'
_chemical_formula_weight         378.24
_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
_audit_creation_date             2022-04-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-04-26 deposited with the CCDC.	2022-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8174(2)
_cell_length_b                   8.2527(3)
_cell_length_c                   31.1764(10)
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.34
_cell_measurement_theta_min      5.55
_cell_volume                     1496.76(9)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            18325
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.356
_diffrn_reflns_theta_min         2.835
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.158
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1368 before and 0.0727 after correction.
The Ratio of minimum to maximum transmission is 0.7389.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_description       Block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1053 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.052(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2710
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0242
_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)+(0.0243P)²+0.8394P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0606
_refine_ls_wR_factor_ref         0.0609
_reflns_Friedel_coverage         0.674
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                2678
_reflns_number_total             2710
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01048h2.cif
_cod_data_source_block           11_CCDC1
_cod_database_code               7158737
_shelx_shelxl_version_number     2018/3
_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   0.820
_shelx_estimated_absorpt_t_min   0.425
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C16(H16), C6(H6), C7(H7), C12(H12), C13(H13), C15(H15)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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 -0.02956(7) 0.87261(6) 0.81934(2) 0.04394(14) Uani 1 1 d . . . . .
S1 S -0.09691(15) 0.67738(10) 0.53064(3) 0.0340(2) Uani 1 1 d . . . . .
O2 O 0.7812(4) 0.9436(3) 0.60802(9) 0.0396(6) Uani 1 1 d . . . . .
O3 O 0.4766(5) 1.0725(3) 0.63353(9) 0.0455(7) Uani 1 1 d . . . . .
O1 O -0.2262(5) 0.4232(3) 0.48401(9) 0.0453(7) Uani 1 1 d . . . . .
N1 N 0.0753(5) 0.3911(3) 0.53085(9) 0.0328(6) Uani 1 1 d . . . . .
H1 H 0.104218 0.288952 0.524793 0.039 Uiso 1 1 calc R . . . .
C9 C 0.5905(5) 0.9524(4) 0.63108(10) 0.0250(7) Uani 1 1 d . . . . .
C8 C 0.5369(6) 0.7900(4) 0.65227(9) 0.0271(7) Uani 1 1 d . . . . .
H8 H 0.686287 0.738060 0.660154 0.033 Uiso 1 1 calc R . . . .
C11 C 0.3984(6) 0.8113(4) 0.69311(10) 0.0259(7) Uani 1 1 d . . . . .
C3 C 0.1328(5) 0.6362(4) 0.56521(10) 0.0262(6) Uani 1 1 d . . . . .
C4 C 0.2425(6) 0.7404(4) 0.59362(10) 0.0272(7) Uani 1 1 d . . . . .
H4 H 0.197662 0.850869 0.595467 0.033 Uiso 1 1 calc R . . . .
C5 C 0.4183(6) 0.6811(4) 0.61926(10) 0.0245(7) Uani 1 1 d . . . . .
C16 C 0.4800(6) 0.7493(4) 0.73179(10) 0.0282(7) Uani 1 1 d . . . . .
H16 H 0.623119 0.693819 0.732246 0.034 Uiso 1 1 calc R . . . .
C2 C 0.2025(6) 0.4763(4) 0.56143(10) 0.0269(7) Uani 1 1 d . . . . .
C6 C 0.4833(7) 0.5188(4) 0.61580(10) 0.0298(7) Uani 1 1 d . . . . .
H6 H 0.602950 0.478452 0.633582 0.036 Uiso 1 1 calc R . . . .
C1 C -0.0944(7) 0.4741(4) 0.51107(11) 0.0328(8) Uani 1 1 d . . . . .
C14 C 0.1490(6) 0.8469(4) 0.76833(10) 0.0294(7) Uani 1 1 d . . . . .
C7 C 0.3770(6) 0.4154(4) 0.58700(11) 0.0335(8) Uani 1 1 d . . . . .
H7 H 0.422815 0.305238 0.584818 0.040 Uiso 1 1 calc R . . . .
C12 C 0.1873(6) 0.8925(5) 0.69336(10) 0.0318(7) Uani 1 1 d . . . . .
H12 H 0.128889 0.936041 0.667347 0.038 Uiso 1 1 calc R . . . .
C13 C 0.0619(6) 0.9105(4) 0.73084(10) 0.0320(7) Uani 1 1 d . . . . .
H13 H -0.081396 0.965720 0.730687 0.038 Uiso 1 1 calc R . . . .
C15 C 0.3571(6) 0.7667(4) 0.76969(11) 0.0319(8) Uani 1 1 d . . . . .
H15 H 0.414754 0.724401 0.795913 0.038 Uiso 1 1 calc R . . . .
C10 C 0.8380(7) 1.0870(5) 0.58350(13) 0.0431(9) Uani 1 1 d . . . . .
H10A H 0.711881 1.112028 0.563744 0.065 Uiso 1 1 calc GR . . . .
H10B H 0.979067 1.067640 0.567098 0.065 Uiso 1 1 calc GR . . . .
H10C H 0.861556 1.178519 0.603052 0.065 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 0.0181 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'
Br Br -0.6763 1.2805 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C3 S1 C1 91.24(17) . . ?
C9 O2 C10 115.7(3) . . ?
C1 N1 C2 116.3(3) . . ?
O2 C9 C8 111.0(3) . . ?
O3 C9 O2 123.0(3) . . ?
O3 C9 C8 126.0(3) . . ?
C9 C8 C5 108.5(2) . . ?
C11 C8 C9 111.7(3) . . ?
C11 C8 C5 113.2(3) . . ?
C16 C11 C8 120.2(3) . . ?
C16 C11 C12 118.1(3) . . ?
C12 C11 C8 121.8(3) . . ?
C4 C3 S1 128.5(3) . . ?
C2 C3 S1 110.9(3) . . ?
C2 C3 C4 120.6(3) . . ?
C5 C4 C3 119.2(3) . . ?
C4 C5 C8 120.8(3) . . ?
C4 C5 C6 119.6(3) . . ?
C6 C5 C8 119.6(3) . . ?
C15 C16 C11 121.5(3) . . ?
C3 C2 N1 112.5(3) . . ?
C7 C2 N1 126.8(3) . . ?
C7 C2 C3 120.7(3) . . ?
C7 C6 C5 121.4(3) . . ?
O1 C1 S1 123.9(3) . . ?
O1 C1 N1 127.1(3) . . ?
N1 C1 S1 109.1(2) . . ?
C13 C14 Br1 117.6(3) . . ?
C13 C14 C15 122.1(3) . . ?
C15 C14 Br1 120.3(3) . . ?
C6 C7 C2 118.5(3) . . ?
C13 C12 C11 121.2(3) . . ?
C14 C13 C12 118.7(3) . . ?
C14 C15 C16 118.4(3) . . ?
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 C14 1.911(3) . ?
S1 C3 1.750(3) . ?
S1 C1 1.785(3) . ?
O2 C9 1.324(4) . ?
O2 C10 1.447(4) . ?
O3 C9 1.195(4) . ?
O1 C1 1.215(4) . ?
N1 C2 1.396(4) . ?
N1 C1 1.351(5) . ?
C9 C8 1.526(4) . ?
C8 C11 1.517(4) . ?
C8 C5 1.531(5) . ?
C11 C16 1.394(4) . ?
C11 C12 1.399(5) . ?
C3 C4 1.390(5) . ?
C3 C2 1.385(5) . ?
C4 C5 1.387(5) . ?
C5 C6 1.396(5) . ?
C16 C15 1.389(5) . ?
C2 C7 1.385(5) . ?
C6 C7 1.384(5) . ?
C14 C13 1.378(5) . ?
C14 C15 1.380(5) . ?
C12 C13 1.386(5) . ?
