#------------------------------------------------------------------------------
#$Date: 2019-11-08 03:53:47 +0200 (Fri, 08 Nov 2019) $
#$Revision: 225218 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/66/7156667.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_7156667
loop_
_publ_author_name
'Miao, Jiankang'
'Zhang, Yahui'
'Sang, Xiaoyan'
'Hao, Wenyan'
_publ_section_title
;
 A silver(i)-catalyzed cascade bicyclization strategy for synthesis of
 5H-benzo[d]tetrazolo[5,1-b][1,3]thiazines.
;
_journal_issue                   9
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2336
_journal_page_last               2340
_journal_paper_doi               10.1039/c8ob03220c
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C12 H10 N4 S'
_chemical_formula_sum            'C12 H0.12 N4 S'
_chemical_formula_weight         232.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-12-03 deposited with the CCDC.
2019-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.8813(8)
_cell_length_b                   8.3305(5)
_cell_length_c                   18.5422(12)
_cell_measurement_temperature    293(2)
_cell_volume                     2298.7(2)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17077
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.246
_diffrn_reflns_theta_min         3.511
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             929
_refine_diff_density_max         0.677
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0615
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0740P)²+1.2719P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1565
_refine_ls_wR_factor_ref         0.1756
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1953
_reflns_number_total             2896
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ob03220c2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7156666--7156667.cif.'
_cod_database_code               7156667
_shelxl_version_number           2014-1
_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, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C1(H1), C4(H4), C2(H2), C3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
S1 S 0.73088(5) 0.57073(9) 0.60404(4) 0.0554(3) Uani 1 1 d .
N1 N 0.84768(12) 0.6751(2) 0.70615(13) 0.0516(5) Uani 1 1 d .
N4 N 0.88861(16) 0.7376(3) 0.59760(16) 0.0732(8) Uani 1 1 d .
N2 N 0.92693(15) 0.7540(3) 0.71155(19) 0.0754(8) Uani 1 1 d .
N3 N 0.95023(17) 0.7884(4) 0.6462(2) 0.0892(10) Uani 1 1 d .
C7 C 0.82553(16) 0.6684(3) 0.63606(16) 0.0511(6) Uani 1 1 d .
C5 C 0.80520(18) 0.6064(3) 0.76721(14) 0.0515(6) Uani 1 1 d .
C9 C 0.64796(15) 0.6815(3) 0.65416(15) 0.0494(6) Uani 1 1 d .
C6 C 0.71161(18) 0.6097(3) 0.77494(14) 0.0503(6) Uani 1 1 d .
C8 C 0.64915(15) 0.6849(3) 0.72479(15) 0.0504(6) Uani 1 1 d .
H8 H 0.6033 0.7440 0.7461 0.060 Uiso 1 1 calc R
C10 C 0.5756(2) 0.7605(4) 0.61192(17) 0.0674(8) Uani 1 1 d .
H10 H 0.5322 0.8203 0.6413 0.081 Uiso 1 1 calc R
C1 C 0.6771(3) 0.5419(4) 0.83819(16) 0.0723(9) Uani 1 1 d .
H1 H 0.6154 0.5440 0.8460 0.087 Uiso 1 1 calc R
C4 C 0.8598(2) 0.5383(4) 0.81986(18) 0.0737(9) Uani 1 1 d .
H4 H 0.9219 0.5388 0.8141 0.088 Uiso 1 1 calc R
C12 C 0.5912(2) 0.8294(4) 0.53983(19) 0.0808(10) Uani 1 1 d .
H12A H 0.5607 0.9288 0.5279 0.097 Uiso 1 1 calc R
H12B H 0.6507 0.8181 0.5191 0.097 Uiso 1 1 calc R
C11 C 0.5364(2) 0.6840(4) 0.54753(18) 0.0784(10) Uani 1 1 d .
H11A H 0.5621 0.5831 0.5316 0.094 Uiso 1 1 calc R
H11B H 0.4720 0.6938 0.5403 0.094 Uiso 1 1 calc R
C2 C 0.7319(3) 0.4724(5) 0.88899(18) 0.0889(13) Uani 1 1 d .
H2 H 0.7067 0.4262 0.9299 0.107 Uiso 1 1 calc R
C3 C 0.8228(4) 0.4705(5) 0.8799(2) 0.0931(12) Uani 1 1 d .
H3 H 0.8594 0.4233 0.9146 0.112 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 0.0033 0.0016 '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'
H H 0.0000 0.0000 '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
C7 S1 C9 98.03(12)
N2 N1 C5 121.7(2)
C7 N1 N2 107.8(2)
C7 N1 C5 130.3(2)
C7 N4 N3 105.1(3)
N3 N2 N1 105.8(3)
N2 N3 N4 111.9(2)
N1 C7 S1 123.46(19)
N4 C7 S1 127.0(2)
N4 C7 N1 109.4(2)
C6 C5 N1 121.2(2)
C4 C5 N1 117.7(3)
C4 C5 C6 121.1(3)
C8 C9 S1 121.19(19)
C8 C9 C10 121.8(2)
C10 C9 S1 116.9(2)
C5 C6 C8 125.3(2)
C1 C6 C5 116.3(3)
C1 C6 C8 118.3(3)
C9 C8 C6 129.6(2)
C12 C10 C9 122.4(3)
C12 C10 C11 59.8(2)
C11 C10 C9 121.5(3)
C2 C1 C6 121.8(3)
C3 C4 C5 120.4(3)
C11 C12 C10 60.1(2)
C12 C11 C10 60.1(2)
C3 C2 C1 120.6(3)
C2 C3 C4 119.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C7 1.732(3)
S1 C9 1.800(3)
N1 N2 1.354(3)
N1 C7 1.342(3)
N1 C5 1.417(4)
N4 N3 1.354(4)
N4 C7 1.312(3)
N2 N3 1.292(4)
C5 C6 1.400(4)
C5 C4 1.391(4)
C9 C8 1.310(4)
C9 C10 1.486(4)
C6 C8 1.456(3)
C6 C1 1.399(4)
C10 C12 1.474(4)
C10 C11 1.474(4)
C1 C2 1.374(5)
C4 C3 1.365(5)
C12 C11 1.468(4)
C2 C3 1.363(6)
