#------------------------------------------------------------------------------
#$Date: 2020-05-04 05:45:07 +0300 (Mon, 04 May 2020) $
#$Revision: 251473 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/81/4038192.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_4038192
loop_
_publ_author_name
'Chen, Jin-Yu'
'Selvaraju, Manikandan'
'Lin, Yen-Tzu'
'Dhole, Sandip'
'Lin, Chih-Yu'
'Sun, Chung-Ming'
_publ_section_title
;
 Molecular Iodine-Promoted [3 + 2] Oxidative Cyclization for the Synthesis
 of Heteroarene-Fused [1,2,4] Thiadiazoles/Selenadiazoles.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5570
_journal_page_last               5579
_journal_paper_doi               10.1021/acs.joc.0c00421
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C16 H16 N2 S'
_chemical_formula_sum            'C16 H16 N2 S'
_chemical_formula_weight         268.37
_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_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 98.536(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6027(2)
_cell_length_b                   14.3253(6)
_cell_length_c                   17.1845(7)
_cell_measurement_reflns_used    5927
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.1064
_cell_measurement_theta_min      2.3969
_cell_volume                     1363.96(9)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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  0.0373
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22423
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.414
_diffrn_reflns_theta_min         1.859
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       columnar
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2777
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0309
_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)+(0.0346P)²+0.5562P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0725
_refine_ls_wR_factor_ref         0.0777
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2322
_reflns_number_total             2777
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00421_si_012.cif
_cod_data_source_block           9'cc
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4038187--4038192.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4038192
_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.
;
_shelxl_version_number           2014/6
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
C1 C 0.3603(2) 0.24088(10) 0.59107(8) 0.0162(3) Uani 1 1 d . . . . .
C2 C 0.3620(3) 0.14648(10) 0.60917(8) 0.0195(3) Uani 1 1 d . . . . .
H2 H 0.2530 0.1217 0.6412 0.023 Uiso 1 1 calc R U . . .
C3 C 0.5256(3) 0.08938(10) 0.57951(8) 0.0206(3) Uani 1 1 d . . . . .
H3 H 0.5298 0.0246 0.5914 0.025 Uiso 1 1 calc R U . . .
C4 C 0.6844(3) 0.12593(10) 0.53235(8) 0.0195(3) Uani 1 1 d . . . . .
H4 H 0.7964 0.0857 0.5127 0.023 Uiso 1 1 calc R U . . .
C5 C 0.6817(2) 0.22024(10) 0.51347(8) 0.0177(3) Uani 1 1 d . . . . .
H5 H 0.7898 0.2444 0.4808 0.021 Uiso 1 1 calc R U . . .
C6 C 0.5183(2) 0.27894(9) 0.54307(8) 0.0153(3) Uani 1 1 d . . . . .
C7 C 0.3301(2) 0.40945(10) 0.56809(8) 0.0172(3) Uani 1 1 d . . . . .
C8 C 0.0958(3) 0.54109(10) 0.61077(8) 0.0202(3) Uani 1 1 d . . . . .
H8A H -0.0413 0.4976 0.6114 0.024 Uiso 1 1 calc R U . . .
H8B H 0.0316 0.5993 0.5845 0.024 Uiso 1 1 calc R U . . .
C9 C 0.2047(3) 0.56350(10) 0.69520(8) 0.0212(3) Uani 1 1 d . . . . .
H9A H 0.3626 0.5946 0.6954 0.025 Uiso 1 1 calc R U . . .
H9B H 0.2329 0.5047 0.7254 0.025 Uiso 1 1 calc R U . . .
C10 C 0.0395(3) 0.62702(10) 0.73521(8) 0.0215(3) Uani 1 1 d . . . . .
H10A H -0.1259 0.6009 0.7269 0.026 Uiso 1 1 calc R U . . .
H10B H 0.0967 0.6279 0.7925 0.026 Uiso 1 1 calc R U . . .
C11 C 0.0317(3) 0.72574(10) 0.70431(8) 0.0185(3) Uani 1 1 d . . . . .
C12 C 0.2230(3) 0.78655(11) 0.72823(9) 0.0254(3) Uani 1 1 d . . . . .
H12 H 0.3564 0.7655 0.7646 0.030 Uiso 1 1 calc R U . . .
C13 C 0.2221(3) 0.87675(11) 0.69999(10) 0.0281(4) Uani 1 1 d . . . . .
H13 H 0.3535 0.9172 0.7173 0.034 Uiso 1 1 calc R U . . .
C14 C 0.0297(3) 0.90832(11) 0.64647(9) 0.0254(3) Uani 1 1 d . . . . .
H14 H 0.0285 0.9704 0.6271 0.031 Uiso 1 1 calc R U . . .
C15 C -0.1603(3) 0.84883(11) 0.62153(9) 0.0253(3) Uani 1 1 d . . . . .
H15 H -0.2919 0.8700 0.5844 0.030 Uiso 1 1 calc R U . . .
C16 C -0.1600(3) 0.75839(10) 0.65039(9) 0.0213(3) Uani 1 1 d . . . . .
H16 H -0.2923 0.7183 0.6331 0.026 Uiso 1 1 calc R U . . .
N1 N 0.4972(2) 0.37463(8) 0.53041(7) 0.0177(3) Uani 1 1 d . . . . .
N2 N 0.2677(2) 0.49959(8) 0.56549(7) 0.0221(3) Uani 1 1 d . . . . .
H2A H 0.3356 0.5364 0.5341 0.027 Uiso 1 1 calc R U . . .
S1 S 0.18202(6) 0.32916(2) 0.62228(2) 0.01840(11) Uani 1 1 d . . . . .
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
C2 C1 C6 121.70(13) . . ?
C2 C1 S1 128.52(11) . . ?
C6 C1 S1 109.77(10) . . ?
C3 C2 C1 118.51(13) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 120.57(13) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 121.09(13) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119.11(13) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
N1 C6 C5 125.68(12) . . ?
N1 C6 C1 115.31(12) . . ?
C5 C6 C1 119.01(12) . . ?
N1 C7 N2 123.54(13) . . ?
N1 C7 S1 116.00(10) . . ?
N2 C7 S1 120.44(10) . . ?
N2 C8 C9 113.14(12) . . ?
N2 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N2 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 C10 111.68(12) . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 112.75(11) . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C16 C11 C12 118.01(14) . . ?
C16 C11 C10 121.92(13) . . ?
C12 C11 C10 120.05(13) . . ?
C13 C12 C11 121.23(14) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 120.09(14) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 119.51(15) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 120.35(14) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 120.80(14) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C7 N1 C6 110.36(12) . . ?
C7 N2 C8 124.65(12) . . ?
C7 N2 H2A 117.7 . . ?
C8 N2 H2A 117.7 . . ?
C1 S1 C7 88.55(7) . . ?
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
C1 C2 1.387(2) . ?
C1 C6 1.4064(19) . ?
C1 S1 1.7446(14) . ?
C2 C3 1.381(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3935(19) . ?
C5 H5 0.9500 . ?
C6 N1 1.3902(17) . ?
C7 N1 1.3131(18) . ?
C7 N2 1.3368(18) . ?
C7 S1 1.7629(14) . ?
C8 N2 1.4523(17) . ?
C8 C9 1.523(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5319(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.509(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.391(2) . ?
C11 C12 1.395(2) . ?
C12 C13 1.380(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
N2 H2A 0.8800 . ?
