#------------------------------------------------------------------------------
#$Date: 2022-06-25 03:28:54 +0300 (Sat, 25 Jun 2022) $
#$Revision: 276265 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/87/7158738.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_7158738
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      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                 107.614(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.2756(7)
_cell_length_b                   5.8934(3)
_cell_length_c                   15.8085(6)
_cell_measurement_reflns_used    9129
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.17
_cell_measurement_theta_min      5.37
_cell_volume                     1534.04(12)
_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  0.0603
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            31455
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.160
_diffrn_reflns_theta_min         2.683
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.033
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6327
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1133 before and 0.0813 after correction.
The Ratio of minimum to maximum transmission is 0.8396.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3024
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.183
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0297
_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)+(0.0277P)²+1.1439P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0793
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2771
_reflns_number_total             3024
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01048h2.cif
_cod_data_source_block           11_CCDC2
_cod_database_code               7158738
_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:
 C009(H009)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F), C00H(H00H), C00J(H00J),
 C00K(H00K), C00L(H00L)
2.c Idealised Me refined as rotating group:
 C00M(H00A,H00C,H00G)
;
_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
Br01 Br 0.62995(2) 0.27451(5) 1.00222(2) 0.03787(10) Uani 1 1 d . . . . .
S002 S 0.19582(4) 0.18153(10) 0.50696(4) 0.03498(15) Uani 1 1 d . . . . .
O003 O 0.29360(9) 0.3693(3) 0.65050(10) 0.0310(3) Uani 1 1 d . . . . .
O004 O 0.25631(10) 0.8415(3) 0.76954(12) 0.0329(4) Uani 1 1 d . . . . .
O005 O 0.21003(10) 0.4859(3) 0.77236(11) 0.0334(4) Uani 1 1 d . . . . .
N006 N 0.18254(11) 0.5853(3) 0.56991(12) 0.0276(4) Uani 1 1 d . . . . .
C007 C 0.39574(13) 0.4899(4) 0.77987(14) 0.0251(4) Uani 1 1 d . . . . .
C008 C 0.11644(13) 0.5577(4) 0.49361(14) 0.0273(4) Uani 1 1 d . . . . .
C009 C 0.31915(13) 0.5603(4) 0.70940(14) 0.0267(4) Uani 1 1 d . . . . .
H009 H 0.330221 0.694046 0.675856 0.032 Uiso 1 1 calc R . . . .
C00A C 0.25358(12) 0.6198(4) 0.75274(14) 0.0262(4) Uani 1 1 d . . . . .
C00B C 0.39931(14) 0.2816(4) 0.82259(16) 0.0291(5) Uani 1 1 d . . . . .
H00B H 0.353914 0.182182 0.805827 0.035 Uiso 1 1 calc R . . . .
C00C C 0.53404(13) 0.3657(4) 0.91255(14) 0.0280(4) Uani 1 1 d . . . . .
C00D C 0.53201(13) 0.5738(4) 0.87181(15) 0.0299(5) Uani 1 1 d . . . . .
H00D H 0.577433 0.673006 0.889174 0.036 Uiso 1 1 calc R . . . .
C00E C 0.46215(13) 0.6354(4) 0.80483(14) 0.0281(4) Uani 1 1 d . . . . .
H00E H 0.459809 0.777773 0.775975 0.034 Uiso 1 1 calc R . . . .
C00F C 0.46866(14) 0.2183(4) 0.88940(15) 0.0296(5) Uani 1 1 d . . . . .
H00F H 0.471212 0.076442 0.918685 0.035 Uiso 1 1 calc R . . . .
C00G C 0.11343(14) 0.3493(4) 0.44980(15) 0.0298(5) Uani 1 1 d . . . . .
C00H C 0.05122(15) 0.2975(4) 0.37272(16) 0.0346(5) Uani 1 1 d . . . . .
H00H H 0.049992 0.156401 0.343312 0.041 Uiso 1 1 calc R . . . .
C00I C 0.22597(13) 0.4043(4) 0.58271(14) 0.0282(4) Uani 1 1 d . . . . .
C00J C 0.05537(14) 0.7173(4) 0.45975(16) 0.0312(5) Uani 1 1 d . . . . .
H00J H 0.056293 0.859172 0.488586 0.037 Uiso 1 1 calc R . . . .
C00K C -0.00678(14) 0.6654(4) 0.38322(17) 0.0358(5) Uani 1 1 d . . . . .
H00K H -0.048710 0.773065 0.359671 0.043 Uiso 1 1 calc R . . . .
C00L C -0.00871(15) 0.4587(5) 0.34046(16) 0.0377(6) Uani 1 1 d . . . . .
H00L H -0.051948 0.427310 0.288129 0.045 Uiso 1 1 calc R . . . .
C00M C 0.19887(16) 0.9240(5) 0.8127(2) 0.0424(6) Uani 1 1 d . . . . .
H00A H 0.143468 0.903623 0.773064 0.064 Uiso 1 1 calc GR . . . .
H00C H 0.208806 1.085481 0.826613 0.064 Uiso 1 1 calc GR . . . .
H00G H 0.205477 0.838789 0.867680 0.064 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
C00G S002 C00I 87.50(11) . . ?
C00I O003 C009 114.74(17) . . ?
C00A O004 C00M 115.83(18) . . ?
C00I N006 C008 108.99(19) . . ?
C00B C007 C009 120.07(19) . . ?
C00E C007 C009 120.28(19) . . ?
C00E C007 C00B 119.6(2) . . ?
N006 C008 C00G 115.2(2) . . ?
C00J C008 N006 125.4(2) . . ?
C00J C008 C00G 119.4(2) . . ?
O003 C009 C007 106.91(17) . . ?
O003 C009 C00A 110.13(17) . . ?
C007 C009 C00A 109.57(17) . . ?
O004 C00A C009 109.12(17) . . ?
O005 C00A O004 125.7(2) . . ?
O005 C00A C009 125.1(2) . . ?
C00F C00B C007 120.5(2) . . ?
C00D C00C Br01 119.45(17) . . ?
C00D C00C C00F 122.1(2) . . ?
C00F C00C Br01 118.48(18) . . ?
C00C C00D C00E 118.7(2) . . ?
C007 C00E C00D 120.4(2) . . ?
C00C C00F C00B 118.7(2) . . ?
C008 C00G S002 109.75(17) . . ?
C00H C00G S002 128.44(19) . . ?
C00H C00G C008 121.8(2) . . ?
C00L C00H C00G 117.7(2) . . ?
O003 C00I S002 116.07(16) . . ?
N006 C00I S002 118.51(17) . . ?
N006 C00I O003 125.4(2) . . ?
C00K C00J C008 118.8(2) . . ?
C00J C00K C00L 121.1(2) . . ?
C00H C00L C00K 121.2(2) . . ?
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
Br01 C00C 1.903(2) . ?
S002 C00G 1.744(2) . ?
S002 C00I 1.747(2) . ?
O003 C009 1.442(3) . ?
O003 C00I 1.341(3) . ?
O004 C00A 1.331(3) . ?
O004 C00M 1.448(3) . ?
O005 C00A 1.194(3) . ?
N006 C008 1.397(3) . ?
N006 C00I 1.284(3) . ?
C007 C009 1.507(3) . ?
C007 C00B 1.393(3) . ?
C007 C00E 1.390(3) . ?
C008 C00G 1.403(3) . ?
C008 C00J 1.394(3) . ?
C009 C00A 1.531(3) . ?
C00B C00F 1.387(3) . ?
C00C C00D 1.381(3) . ?
C00C C00F 1.384(3) . ?
C00D C00E 1.391(3) . ?
C00G C00H 1.393(3) . ?
C00H C00L 1.383(4) . ?
C00J C00K 1.387(4) . ?
C00K C00L 1.389(4) . ?
