#------------------------------------------------------------------------------
#$Date: 2022-04-15 01:15:14 +0300 (Fri, 15 Apr 2022) $
#$Revision: 274534 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/68/1566802.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_1566802
loop_
_publ_author_name
'Begam, Hasina Mamataj'
'Nandi, Shantanu'
'Jana, Ranjan'
_publ_section_title
;
 Directing group switch in copper-catalyzed electrophilic C--H
 amination/migratory annulation cascade: divergent access to
 benzimidazolone/benzimidazole
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC01420C
_journal_year                    2022
_chemical_compound_source        synthetic
_chemical_formula_moiety         'C16 H12 N2 S'
_chemical_formula_sum            'C16 H12 N2 S'
_chemical_formula_weight         264.34
_chemical_melting_point          398
_chemical_name_common            HM
_chemical_name_systematic        HM-643S
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2020-07-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2020-08-25 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.2550(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1282(2)
_cell_length_b                   14.1422(4)
_cell_length_c                   14.4603(4)
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      66.819
_cell_measurement_theta_min      4.382
_cell_volume                     1247.95(6)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0469
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19122
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.813
_diffrn_reflns_theta_max         66.813
_diffrn_reflns_theta_min         4.382
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.167
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1175 before and 0.0649 after correction. The Ratio of minimum to maximum transmission is 0.8791. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       chloroform
_exptl_crystal_F_000             552
_exptl_crystal_preparation       'in CHCl3'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2213
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0361
_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)+(0.0416P)²+0.8469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0929
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2132
_reflns_number_total             2213
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc01420c2.cif
_cod_data_source_block           hm_643s_0m_a
_cod_database_code               1566802
_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   0.671
_shelx_estimated_absorpt_t_min   0.671
_exptl_absorpt_special_details   Nothing
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N002(H002), C008(H008), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D),
 C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J)
;
_olex2_submission_original_sample_id HM-643S
_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
S001 S 0.32381(7) 0.73439(3) 0.51266(3) 0.02613(16) Uani 1 1 d . . . . .
N002 N 0.2431(2) 0.67280(9) 0.68340(9) 0.0175(3) Uani 1 1 d . . . . .
H002 H 0.297589 0.673681 0.741861 0.021 Uiso 1 1 calc R . . . .
N003 N 0.5461(2) 0.76710(9) 0.77541(9) 0.0189(3) Uani 1 1 d . . . . .
C004 C 0.5528(3) 0.76989(11) 0.68265(11) 0.0177(3) Uani 1 1 d . . . . .
C005 C 0.0489(2) 0.62000(11) 0.66875(11) 0.0173(3) Uani 1 1 d . . . . .
C006 C -0.2565(3) 0.54361(11) 0.73852(11) 0.0195(3) Uani 1 1 d . . . . .
C007 C -0.0531(2) 0.59302(11) 0.75054(11) 0.0175(3) Uani 1 1 d . . . . .
C008 C -0.2426(3) 0.54441(12) 0.57237(12) 0.0235(4) Uani 1 1 d . . . . .
H008 H -0.304769 0.527077 0.512158 0.028 Uiso 1 1 calc R . . . .
C009 C 0.3634(3) 0.72223(11) 0.62712(11) 0.0178(3) Uani 1 1 d . . . . .
C00A C -0.0713(3) 0.58789(12) 0.91763(11) 0.0232(4) Uani 1 1 d . . . . .
H00A H -0.008155 0.602099 0.978500 0.028 Uiso 1 1 calc R . . . .
C00B C 0.0356(3) 0.61339(11) 0.84234(11) 0.0192(3) Uani 1 1 d . . . . .
H00B H 0.172125 0.645399 0.851838 0.023 Uiso 1 1 calc R . . . .
C00C C 0.7223(3) 0.81233(11) 0.64053(11) 0.0204(4) Uani 1 1 d . . . . .
H00C H 0.722396 0.812882 0.574836 0.024 Uiso 1 1 calc R . . . .
C00D C 0.7109(3) 0.80709(12) 0.82845(11) 0.0212(4) Uani 1 1 d . . . . .
H00D H 0.707890 0.805109 0.893992 0.025 Uiso 1 1 calc R . . . .
C00E C -0.3481(3) 0.51976(12) 0.64809(12) 0.0223(4) Uani 1 1 d . . . . .
H00E H -0.483197 0.486515 0.640022 0.027 Uiso 1 1 calc R . . . .
C00F C -0.0449(3) 0.59469(12) 0.58160(11) 0.0213(4) Uani 1 1 d . . . . .
H00F H 0.025001 0.611432 0.527931 0.026 Uiso 1 1 calc R . . . .
C00G C 0.8865(3) 0.85145(12) 0.79209(12) 0.0231(4) Uani 1 1 d . . . . .
H00G H 1.000605 0.879434 0.831873 0.028 Uiso 1 1 calc R . . . .
C00H C -0.2747(3) 0.54061(13) 0.90530(12) 0.0259(4) Uani 1 1 d . . . . .
H00H H -0.349349 0.523932 0.957702 0.031 Uiso 1 1 calc R . . . .
C00I C -0.3637(3) 0.51894(12) 0.81809(12) 0.0233(4) Uani 1 1 d . . . . .
H00I H -0.500179 0.486699 0.810366 0.028 Uiso 1 1 calc R . . . .
C00J C 0.8915(3) 0.85395(12) 0.69657(12) 0.0230(4) Uani 1 1 d . . . . .
H00J H 1.009464 0.883802 0.669731 0.028 Uiso 1 1 calc R . . . .
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'
N N 0.0311 0.0180 '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
C005 N002 H002 113.2 . . ?
C009 N002 H002 113.2 . . ?
C009 N002 C005 133.60(14) . . ?
C00D N003 C004 117.99(14) . . ?
N003 C004 C009 115.17(14) . . ?
N003 C004 C00C 122.82(15) . . ?
C00C C004 C009 122.01(14) . . ?
N002 C005 C007 116.29(14) . . ?
C00F C005 N002 123.39(14) . . ?
C00F C005 C007 120.32(15) . . ?
C00E C006 C007 119.84(15) . . ?
C00E C006 C00I 121.09(15) . . ?
C00I C006 C007 119.07(15) . . ?
C006 C007 C005 118.07(14) . . ?
C00B C007 C005 123.89(15) . . ?
C00B C007 C006 118.04(14) . . ?
C00E C008 H008 119.3 . . ?
C00E C008 C00F 121.44(16) . . ?
C00F C008 H008 119.3 . . ?
N002 C009 S001 128.33(13) . . ?
N002 C009 C004 110.37(13) . . ?
C004 C009 S001 121.30(12) . . ?
C00B C00A H00A 119.8 . . ?
C00B C00A C00H 120.38(16) . . ?
C00H C00A H00A 119.8 . . ?
C007 C00B H00B 119.3 . . ?
C00A C00B C007 121.37(15) . . ?
C00A C00B H00B 119.3 . . ?
C004 C00C H00C 120.8 . . ?
C00J C00C C004 118.47(15) . . ?
C00J C00C H00C 120.8 . . ?
N003 C00D H00D 118.5 . . ?
N003 C00D C00G 122.98(15) . . ?
C00G C00D H00D 118.5 . . ?
C006 C00E H00E 119.9 . . ?
C008 C00E C006 120.18(15) . . ?
C008 C00E H00E 119.9 . . ?
C005 C00F C008 120.10(15) . . ?
C005 C00F H00F 119.9 . . ?
C008 C00F H00F 119.9 . . ?
C00D C00G H00G 120.7 . . ?
C00J C00G C00D 118.52(15) . . ?
C00J C00G H00G 120.7 . . ?
C00A C00H H00H 120.1 . . ?
C00I C00H C00A 119.84(15) . . ?
C00I C00H H00H 120.1 . . ?
C006 C00I H00I 119.4 . . ?
C00H C00I C006 121.28(16) . . ?
C00H C00I H00I 119.4 . . ?
C00C C00J H00J 120.4 . . ?
C00G C00J C00C 119.22(15) . . ?
C00G C00J H00J 120.4 . . ?
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
S001 C009 1.6595(16) . ?
N002 H002 0.8800 . ?
N002 C005 1.405(2) . ?
N002 C009 1.343(2) . ?
N003 C004 1.346(2) . ?
N003 C00D 1.336(2) . ?
C004 C009 1.509(2) . ?
C004 C00C 1.388(2) . ?
C005 C007 1.439(2) . ?
C005 C00F 1.383(2) . ?
C006 C007 1.426(2) . ?
C006 C00E 1.416(2) . ?
C006 C00I 1.420(2) . ?
C007 C00B 1.417(2) . ?
C008 H008 0.9500 . ?
C008 C00E 1.367(2) . ?
C008 C00F 1.401(2) . ?
C00A H00A 0.9500 . ?
C00A C00B 1.369(2) . ?
C00A C00H 1.411(2) . ?
C00B H00B 0.9500 . ?
C00C H00C 0.9500 . ?
C00C C00J 1.387(2) . ?
C00D H00D 0.9500 . ?
C00D C00G 1.390(2) . ?
C00E H00E 0.9500 . ?
C00F H00F 0.9500 . ?
C00G H00G 0.9500 . ?
C00G C00J 1.385(2) . ?
C00H H00H 0.9500 . ?
C00H C00I 1.362(3) . ?
C00I H00I 0.9500 . ?
C00J H00J 0.9500 . ?
