#------------------------------------------------------------------------------
#$Date: 2022-06-25 03:28:54 +0300 (Sat, 25 Jun 2022) $
#$Revision: 276265 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/87/7158739.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_7158739
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 H11 Br Cl N O3 S'
_chemical_formula_sum            'C16 H11 Br Cl N O3 S'
_chemical_formula_weight         412.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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                 96.1360(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1958(3)
_cell_length_b                   15.7734(5)
_cell_length_c                   9.1550(3)
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.57
_cell_measurement_theta_min      3.97
_cell_volume                     1607.47(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      100.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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  0.0557
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            29115
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.561
_diffrn_reflns_theta_min         3.971
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.355
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6268
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1261 before and 0.0633 after correction.
The Ratio of minimum to maximum transmission is 0.8317.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3180
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0234
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0317P)²+0.6734P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0593
_refine_ls_wR_factor_ref         0.0607
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2894
_reflns_number_total             3180
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01048h2.cif
_cod_data_source_block           11_CCDC3
_cod_database_code               7158739
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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:
 C15(H15), C16(H16), C13(H13), C12(H12), C2(H2), C4(H4), C3(H3)
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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.27928(2) 0.75492(2) 1.14519(2) 0.02219(7) Uani 1 1 d . . . . .
Cl1 Cl 0.13321(4) 0.56051(3) 0.42301(5) 0.02221(11) Uani 1 1 d . . . . .
S1 S 0.47322(4) 0.32975(3) 0.58425(5) 0.02044(11) Uani 1 1 d . . . . .
O1 O 0.38566(11) 0.35622(9) 0.83865(13) 0.0194(3) Uani 1 1 d . . . . .
O3 O 0.14150(12) 0.30801(8) 0.71190(14) 0.0203(3) Uani 1 1 d . . . . .
O2 O 0.11625(12) 0.37990(8) 0.91904(14) 0.0206(3) Uani 1 1 d . . . . .
N1 N 0.29613(13) 0.42755(10) 0.63702(15) 0.0152(3) Uani 1 1 d . . . . .
C6 C 0.30140(15) 0.43348(11) 0.48452(19) 0.0148(3) Uani 1 1 d . . . . .
C14 C 0.25547(16) 0.66411(11) 1.00855(18) 0.0161(3) Uani 1 1 d . . . . .
C15 C 0.35415(16) 0.62351(11) 0.96184(19) 0.0168(3) Uani 1 1 d . . . . .
H15 H 0.433343 0.641585 0.995099 0.020 Uiso 1 1 calc R . . . .
C16 C 0.33490(16) 0.55563(11) 0.86513(19) 0.0157(3) Uani 1 1 d . . . . .
H16 H 0.401812 0.527272 0.831926 0.019 Uiso 1 1 calc R . . . .
C9 C 0.14870(15) 0.37659(11) 0.79908(19) 0.0164(3) Uani 1 1 d . . . . .
C13 C 0.13915(16) 0.63974(12) 0.95993(19) 0.0174(4) Uani 1 1 d . . . . .
H13 H 0.072495 0.669140 0.991648 0.021 Uiso 1 1 calc R . . . .
C11 C 0.21926(16) 0.52867(11) 0.81633(18) 0.0145(3) Uani 1 1 d . . . . .
C8 C 0.19478(15) 0.45298(11) 0.71616(18) 0.0148(3) Uani 1 1 d . . . . .
H8 H 0.128231 0.469779 0.640047 0.018 Uiso 1 1 calc R . . . .
C12 C 0.12167(16) 0.57179(11) 0.86429(19) 0.0174(4) Uani 1 1 d . . . . .
H12 H 0.042257 0.554251 0.830844 0.021 Uiso 1 1 calc R . . . .
C7 C 0.37987(16) 0.37297(11) 0.70876(19) 0.0163(3) Uani 1 1 d . . . . .
C2 C 0.25163(17) 0.47409(12) 0.2313(2) 0.0196(4) Uani 1 1 d . . . . .
H2 H 0.204294 0.506790 0.159652 0.024 Uiso 1 1 calc R . . . .
C4 C 0.40881(17) 0.37208(12) 0.2904(2) 0.0209(4) Uani 1 1 d . . . . .
H4 H 0.469326 0.335339 0.261555 0.025 Uiso 1 1 calc R . . . .
C5 C 0.39060(16) 0.38081(12) 0.4372(2) 0.0175(4) Uani 1 1 d . . . . .
C3 C 0.33649(18) 0.41831(13) 0.1867(2) 0.0222(4) Uani 1 1 d . . . . .
H3 H 0.345040 0.411798 0.085231 0.027 Uiso 1 1 calc R . . . .
C1 C 0.23460(16) 0.48301(11) 0.3785(2) 0.0167(3) Uani 1 1 d . . . . .
C10 C 0.1017(2) 0.23137(13) 0.7790(3) 0.0276(4) Uani 1 1 d . . . . .
H10A H 0.109964 0.183180 0.713289 0.041 Uiso 1 1 calc GR . . . .
H10B H 0.017277 0.237488 0.796568 0.041 Uiso 1 1 calc GR . . . .
H10C H 0.150827 0.221559 0.872628 0.041 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'
Cl Cl 0.3639 0.7018 '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
C5 S1 C7 91.06(8) . . ?
C9 O3 C10 114.99(15) . . ?
C6 N1 C8 126.09(14) . . ?
C7 N1 C6 114.44(14) . . ?
C7 N1 C8 117.12(14) . . ?
C5 C6 N1 111.96(15) . . ?
C1 C6 N1 130.51(16) . . ?
C1 C6 C5 117.52(16) . . ?
C15 C14 Br1 119.44(13) . . ?
C15 C14 C13 121.78(16) . . ?
C13 C14 Br1 118.78(13) . . ?
C14 C15 C16 118.58(16) . . ?
C11 C16 C15 121.03(16) . . ?
O3 C9 C8 109.83(14) . . ?
O2 C9 O3 125.28(17) . . ?
O2 C9 C8 124.70(16) . . ?
C12 C13 C14 118.85(17) . . ?
C16 C11 C8 122.58(16) . . ?
C16 C11 C12 118.86(16) . . ?
C12 C11 C8 118.54(15) . . ?
N1 C8 C9 110.30(14) . . ?
N1 C8 C11 114.58(14) . . ?
C11 C8 C9 111.52(14) . . ?
C13 C12 C11 120.88(16) . . ?
O1 C7 S1 125.17(14) . . ?
O1 C7 N1 124.23(16) . . ?
N1 C7 S1 110.58(12) . . ?
C3 C2 C1 121.25(17) . . ?
C3 C4 C5 118.35(17) . . ?
C6 C5 S1 111.75(13) . . ?
C4 C5 S1 125.48(15) . . ?
C4 C5 C6 122.77(17) . . ?
C4 C3 C2 120.04(17) . . ?
C6 C1 Cl1 122.83(14) . . ?
C2 C1 Cl1 117.23(14) . . ?
C2 C1 C6 119.87(17) . . ?
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 1.9017(17) . ?
Cl1 C1 1.7457(19) . ?
S1 C7 1.7638(18) . ?
S1 C5 1.7467(18) . ?
O1 C7 1.213(2) . ?
O3 C9 1.342(2) . ?
O3 C10 1.448(2) . ?
O2 C9 1.194(2) . ?
N1 C6 1.407(2) . ?
N1 C8 1.466(2) . ?
N1 C7 1.386(2) . ?
C6 C5 1.403(3) . ?
C6 C1 1.399(2) . ?
C14 C15 1.384(3) . ?
C14 C13 1.385(3) . ?
C15 C16 1.391(3) . ?
C16 C11 1.390(2) . ?
C9 C8 1.542(2) . ?
C13 C12 1.385(3) . ?
C11 C8 1.513(2) . ?
C11 C12 1.397(2) . ?
C2 C3 1.388(3) . ?
C2 C1 1.389(3) . ?
C4 C5 1.388(3) . ?
C4 C3 1.387(3) . ?
