#------------------------------------------------------------------------------
#$Date: 2020-10-04 06:36:40 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257136 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/87/4038774.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_4038774
loop_
_publ_author_name
'Geng, Xinyu'
'Liu, Siyuan'
'Wang, Wenyao'
'Qu, Jingping'
'Wang, Baomin'
_publ_section_title
;
 tert-Amino Effect-Promoted Rearrangement of Aryl Isothiocyanate: A
 Versatile Approach to Benzimidazothiazepines and Benzimidazothioethers.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12635
_journal_page_last               12643
_journal_paper_doi               10.1021/acs.joc.0c01806
_journal_volume                  85
_journal_year                    2020
_chemical_formula_sum            'C11 H12 N2 S'
_chemical_formula_weight         204.29
_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_method           SHELXL-2014/7
_cell_angle_alpha                89.0396(17)
_cell_angle_beta                 72.6274(16)
_cell_angle_gamma                80.7426(17)
_cell_formula_units_Z            2
_cell_length_a                   6.5847(7)
_cell_length_b                   8.4285(9)
_cell_length_c                   9.4274(11)
_cell_measurement_reflns_used    8370
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.36
_cell_measurement_theta_min      2.45
_cell_volume                     492.57(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9526
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.450
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       needle
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_transmission_factor_max   0.7456
_exptl_transmission_factor_min   0.5917
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    'riding mode'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1725
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0303
_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)+(0.0365P)²+0.3392P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0815
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1590
_reflns_number_total             1725
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01806_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 4038774.cif.'
_cod_database_code               4038774
_shelx_shelxl_version_number     2014/7
_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_min   0.904
_shelx_estimated_absorpt_t_max   0.989
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
S1 S 0.25623(6) 0.77713(5) 0.20915(4) 0.02344(15) Uani 1 1 d . . . . .
N1 N 0.6429(2) 0.78347(15) -0.00169(14) 0.0184(3) Uani 1 1 d . . . . .
N2 N 0.3552(2) 0.81990(15) -0.08878(15) 0.0206(3) Uani 1 1 d . . . . .
C3 C 0.7683(2) 0.75986(19) 0.10359(18) 0.0215(3) Uani 1 1 d . . . . .
H3A H 0.7046 0.8411 0.1860 0.026 Uiso 1 1 calc R U . . .
H3B H 0.9173 0.7778 0.0527 0.026 Uiso 1 1 calc R U . . .
C4 C 0.3705(3) 0.57667(19) 0.25197(19) 0.0254(4) Uani 1 1 d . . . . .
H4A H 0.2612 0.5360 0.3348 0.030 Uiso 1 1 calc R U . . .
H4B H 0.3994 0.5042 0.1642 0.030 Uiso 1 1 calc R U . . .
C5 C 0.4240(2) 0.79406(18) 0.02879(17) 0.0189(3) Uani 1 1 d . . . . .
C6 C 0.9333(2) 0.79935(19) -0.24659(18) 0.0224(4) Uani 1 1 d . . . . .
H6A H 1.0542 0.7838 -0.2097 0.027 Uiso 1 1 calc R U . . .
C7 C 0.7765(3) 0.5924(2) 0.16815(18) 0.0244(4) Uani 1 1 d . . . . .
H7A H 0.7979 0.5126 0.0870 0.029 Uiso 1 1 calc R U . . .
H7B H 0.9039 0.5700 0.2050 0.029 Uiso 1 1 calc R U . . .
C8 C 0.7227(2) 0.80325(17) -0.15319(17) 0.0183(3) Uani 1 1 d . . . . .
C9 C 0.9548(3) 0.8195(2) -0.39602(18) 0.0264(4) Uani 1 1 d . . . . .
H9A H 1.0949 0.8171 -0.4639 0.032 Uiso 1 1 calc R U . . .
C10 C 0.5773(3) 0.5672(2) 0.29452(18) 0.0262(4) Uani 1 1 d . . . . .
H10A H 0.5533 0.6491 0.3744 0.031 Uiso 1 1 calc R U . . .
H10B H 0.6075 0.4604 0.3360 0.031 Uiso 1 1 calc R U . . .
C11 C 0.5418(2) 0.82727(18) -0.20498(17) 0.0194(3) Uani 1 1 d . . . . .
C12 C 0.5687(3) 0.84865(19) -0.35702(18) 0.0239(4) Uani 1 1 d . . . . .
H12A H 0.4484 0.8662 -0.3945 0.029 Uiso 1 1 calc R U . . .
C13 C 0.7764(3) 0.8433(2) -0.45023(18) 0.0269(4) Uani 1 1 d . . . . .
H13A H 0.7987 0.8560 -0.5538 0.032 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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 C4 100.46(7) . . ?
C5 N1 C8 106.08(12) . . ?
C5 N1 C3 127.52(13) . . ?
C8 N1 C3 126.38(12) . . ?
C5 N2 C11 104.07(12) . . ?
N1 C3 C7 113.23(12) . . ?
C10 C4 S1 115.25(11) . . ?
N2 C5 N1 113.95(13) . . ?
N2 C5 S1 124.29(12) . . ?
N1 C5 S1 121.76(12) . . ?
C9 C6 C8 115.94(15) . . ?
C10 C7 C3 115.41(14) . . ?
N1 C8 C6 131.56(14) . . ?
N1 C8 C11 105.40(13) . . ?
C6 C8 C11 123.02(14) . . ?
C6 C9 C13 121.99(15) . . ?
C7 C10 C4 115.41(14) . . ?
N2 C11 C12 129.77(14) . . ?
N2 C11 C8 110.49(13) . . ?
C12 C11 C8 119.71(14) . . ?
C13 C12 C11 117.62(15) . . ?
C12 C13 C9 121.72(15) . . ?
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
S1 C5 1.7473(15) . ?
S1 C4 1.8256(17) . ?
N1 C5 1.371(2) . ?
N1 C8 1.384(2) . ?
N1 C3 1.4616(19) . ?
N2 C5 1.320(2) . ?
N2 C11 1.390(2) . ?
C3 C7 1.527(2) . ?
C4 C10 1.521(2) . ?
C6 C9 1.383(2) . ?
C6 C8 1.398(2) . ?
C7 C10 1.527(2) . ?
C8 C11 1.402(2) . ?
C9 C13 1.400(2) . ?
C11 C12 1.403(2) . ?
C12 C13 1.381(2) . ?
