#------------------------------------------------------------------------------
#$Date: 2022-06-25 03:28:54 +0300 (Sat, 25 Jun 2022) $
#$Revision: 276265 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/87/7158736.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_7158736
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 O2 S2'
_chemical_formula_sum            'C16 H12 Br N O2 S2'
_chemical_formula_weight         394.30
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                91.0830(10)
_cell_angle_beta                 93.0320(10)
_cell_angle_gamma                116.6810(10)
_cell_formula_units_Z            2
_cell_length_a                   7.8787(3)
_cell_length_b                   8.2497(4)
_cell_length_c                   13.2573(6)
_cell_measurement_reflns_used    9832
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      65.32
_cell_measurement_theta_min      3.34
_cell_volume                     767.98(6)
_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 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0473
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16708
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        65.317
_diffrn_reflns_theta_max         65.317
_diffrn_reflns_theta_min         3.342
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.242
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.5566
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1035 before and 0.0732 after correction.
The Ratio of minimum to maximum transmission is 0.7396.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.652
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0315
_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)+(0.0326P)²+1.0817P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0813
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2587
_reflns_number_total             2587
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01048h2.cif
_cod_data_source_block           11
_cod_original_cell_volume        767.97(6)
_cod_database_code               7158736
_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:
 C00B(H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L)
2.c Idealised Me refined as rotating group:
 C00M(H00A,H00D,H00H)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
Br01 Br -0.20278(4) 0.71650(4) 1.00744(2) 0.02924(13) Uani 1 1 d . . . . .
S002 S 0.26727(9) 0.29213(8) 0.54840(4) 0.02161(16) Uani 1 1 d . . . . .
S003 S 0.40462(9) 0.24515(8) 0.75466(5) 0.02308(16) Uani 1 1 d . . . . .
O004 O 0.7390(2) 0.7710(2) 0.72874(14) 0.0257(4) Uani 1 1 d . . . . .
O005 O 0.6483(3) 0.9637(2) 0.80228(14) 0.0279(4) Uani 1 1 d . . . . .
N006 N 0.3652(3) 0.5373(3) 0.68937(15) 0.0179(4) Uani 1 1 d . . . . .
C007 C 0.3507(3) 0.3677(3) 0.67363(18) 0.0185(5) Uani 1 1 d . . . . .
C008 C 0.2593(3) 0.4934(3) 0.51873(19) 0.0204(5) Uani 1 1 d . . . . .
C009 C 0.6167(3) 0.8126(3) 0.77424(18) 0.0192(5) Uani 1 1 d . . . . .
C00A C 0.3161(3) 0.6123(3) 0.60530(18) 0.0176(5) Uani 1 1 d . . . . .
C00B C 0.4323(3) 0.6373(3) 0.78745(18) 0.0185(5) Uani 1 1 d . . . . .
H00B H 0.469183 0.560384 0.832114 0.022 Uiso 1 1 calc R . . . .
C00C C 0.2746(4) 0.8323(3) 0.5074(2) 0.0238(5) Uani 1 1 d . . . . .
H00C H 0.276416 0.947810 0.502459 0.029 Uiso 1 1 calc R . . . .
C00D C 0.2771(3) 0.6624(3) 0.83852(18) 0.0195(5) Uani 1 1 d . . . . .
C00E C 0.2149(4) 0.5450(3) 0.42738(19) 0.0235(5) Uani 1 1 d . . . . .
H00E H 0.177792 0.464855 0.369139 0.028 Uiso 1 1 calc R . . . .
C00F C -0.0578(4) 0.5671(4) 0.85790(19) 0.0230(5) Uani 1 1 d . . . . .
H00F H -0.187618 0.492480 0.836453 0.028 Uiso 1 1 calc R . . . .
C00G C 0.0865(4) 0.5538(3) 0.80886(19) 0.0221(5) Uani 1 1 d . . . . .
H00G H 0.054291 0.468275 0.753438 0.026 Uiso 1 1 calc R . . . .
C00H C -0.0087(4) 0.6914(3) 0.93886(18) 0.0216(5) Uani 1 1 d . . . . .
C00I C 0.3214(4) 0.7821(3) 0.60066(19) 0.0225(5) Uani 1 1 d . . . . .
H00I H 0.355823 0.861701 0.659046 0.027 Uiso 1 1 calc R . . . .
C00J C 0.2254(4) 0.7172(4) 0.4219(2) 0.0251(5) Uani 1 1 d . . . . .
H00J H 0.198509 0.756458 0.358765 0.030 Uiso 1 1 calc R . . . .
C00K C 0.1781(4) 0.7961(4) 0.9730(2) 0.0284(6) Uani 1 1 d . . . . .
H00K H 0.208901 0.877879 1.030129 0.034 Uiso 1 1 calc R . . . .
C00L C 0.3210(4) 0.7811(4) 0.9232(2) 0.0274(6) Uani 1 1 d . . . . .
H00L H 0.450246 0.852278 0.946932 0.033 Uiso 1 1 calc R . . . .
C00M C 0.9275(4) 0.9216(4) 0.7211(2) 0.0305(6) Uani 1 1 d . . . . .
H00A H 0.918684 1.008618 0.674379 0.046 Uiso 1 1 calc GR . . . .
H00D H 1.012925 0.875451 0.695827 0.046 Uiso 1 1 calc GR . . . .
H00H H 0.977528 0.982125 0.787995 0.046 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
C008 S002 C007 93.03(12) . . ?
C009 O004 C00M 115.2(2) . . ?
C007 N006 C00A 115.98(19) . . ?
C007 N006 C00B 122.1(2) . . ?
C00A N006 C00B 121.92(19) . . ?
S003 C007 S002 122.60(14) . . ?
N006 C007 S002 109.24(17) . . ?
N006 C007 S003 128.15(19) . . ?
C00A C008 S002 109.69(18) . . ?
C00E C008 S002 129.2(2) . . ?
C00E C008 C00A 121.0(2) . . ?
O004 C009 C00B 109.38(19) . . ?
O005 C009 O004 124.6(2) . . ?
O005 C009 C00B 126.0(2) . . ?
N006 C00A C008 112.0(2) . . ?
C00I C00A N006 127.4(2) . . ?
C00I C00A C008 120.5(2) . . ?
N006 C00B C009 108.66(19) . . ?
N006 C00B C00D 112.72(19) . . ?
C00D C00B C009 115.77(19) . . ?
C00J C00C C00I 121.4(2) . . ?
C00G C00D C00B 120.6(2) . . ?
C00G C00D C00L 118.1(2) . . ?
C00L C00D C00B 120.9(2) . . ?
C008 C00E C00J 118.5(2) . . ?
C00H C00F C00G 118.4(2) . . ?
C00F C00G C00D 121.7(2) . . ?
C00F C00H Br01 119.84(19) . . ?
C00K C00H Br01 118.62(19) . . ?
C00K C00H C00F 121.5(2) . . ?
C00A C00I C00C 117.8(2) . . ?
C00C C00J C00E 120.7(2) . . ?
C00H C00K C00L 119.3(2) . . ?
C00K C00L C00D 120.7(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 C00H 1.906(2) . ?
S002 C007 1.748(2) . ?
S002 C008 1.741(2) . ?
S003 C007 1.654(3) . ?
O004 C009 1.327(3) . ?
O004 C00M 1.457(3) . ?
O005 C009 1.204(3) . ?
N006 C007 1.363(3) . ?
N006 C00A 1.403(3) . ?
N006 C00B 1.465(3) . ?
C008 C00A 1.410(3) . ?
C008 C00E 1.371(4) . ?
C009 C00B 1.543(3) . ?
C00A C00I 1.386(3) . ?
C00B C00D 1.518(3) . ?
C00C C00I 1.394(4) . ?
C00C C00J 1.386(4) . ?
C00D C00G 1.389(4) . ?
C00D C00L 1.398(4) . ?
C00E C00J 1.389(4) . ?
C00F C00G 1.383(4) . ?
C00F C00H 1.383(4) . ?
C00H C00K 1.375(4) . ?
C00K C00L 1.385(4) . ?
