#------------------------------------------------------------------------------
#$Date: 2019-11-04 11:48:55 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222648 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/40/4034087.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_4034087
loop_
_publ_author_name
'Lee, Woohyeong'
'Shin, Changhoon'
'Park, Soo Eun'
'Joo, Jung Min'
_publ_section_title
;
 Regio- and Stereoselective Synthesis of Thiazole-Containing
 Triarylethylenes by Hydroarylation of Alkynes.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12913
_journal_page_last               12924
_journal_paper_doi               10.1021/acs.joc.9b01619
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C17 H13 N S'
_chemical_formula_weight         263.34
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   9.7128(17)
_cell_length_b                   9.7128(17)
_cell_length_c                   12.1114(18)
_cell_measurement_reflns_used    8356
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.42
_cell_volume                     989.5(3)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_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 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Breeze CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12439
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.490
_diffrn_reflns_theta_min         2.421
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       block
_exptl_crystal_F_000             414
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.03(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3233
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0291
_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)+(0.0364P)²+0.1476P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0727
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                3076
_reflns_number_total             3233
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b01619_si_002.cif
_cod_data_source_block           ss
_cod_original_cell_volume        989.5(4)
_cod_database_code               4034087
_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   0.951
_shelx_estimated_absorpt_t_max   0.960
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
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
S1 S -0.15732(6) -0.22141(6) 0.14000(4) 0.03598(14) Uani 1 1 d . .
N1 N -0.3492(2) -0.1372(2) 0.06177(16) 0.0414(4) Uani 1 1 d . .
C1 C 0.4613(3) 0.1048(3) 0.18913(19) 0.0375(5) Uani 1 1 d . .
H1A H 0.4229 0.0012 0.1598 0.045 Uiso 1 1 calc R U
C2 C 0.6172(3) 0.1916(3) 0.2245(2) 0.0460(6) Uani 1 1 d . .
H2A H 0.6851 0.1479 0.2181 0.055 Uiso 1 1 calc R U
C3 C 0.6749(3) 0.3410(3) 0.2691(2) 0.0436(5) Uani 1 1 d . .
H3A H 0.7819 0.4002 0.2937 0.052 Uiso 1 1 calc R U
C4 C 0.5746(3) 0.4040(3) 0.2775(2) 0.0402(5) Uani 1 1 d . .
H4A H 0.6131 0.5066 0.3086 0.048 Uiso 1 1 calc R U
C5 C 0.4197(3) 0.3185(3) 0.24101(19) 0.0352(4) Uani 1 1 d . .
H5A H 0.3527 0.3634 0.2467 0.042 Uiso 1 1 calc R U
C6 C 0.3597(2) 0.1672(2) 0.19586(18) 0.0308(4) Uani 1 1 d . .
C7 C 0.1929(3) 0.0637(2) 0.16316(18) 0.0322(4) Uani 1 1 d . .
H7A H 0.1596 -0.0463 0.1588 0.039 Uiso 1 1 calc R U
C8 C 0.0805(3) 0.1010(2) 0.13844(18) 0.0282(4) Uani 1 1 d . .
C9 C 0.1146(2) 0.2682(2) 0.12784(16) 0.0290(4) Uani 1 1 d . .
C10 C 0.2024(3) 0.3603(3) 0.03819(17) 0.0352(5) Uani 1 1 d . .
H10A H 0.2359 0.3148 -0.0177 0.042 Uiso 1 1 calc R U
C11 C 0.2410(3) 0.5179(3) 0.0302(2) 0.0438(5) Uani 1 1 d . .
H11A H 0.2998 0.5797 -0.0315 0.053 Uiso 1 1 calc R U
C12 C 0.1949(3) 0.5847(3) 0.1106(2) 0.0462(6) Uani 1 1 d . .
H12A H 0.2234 0.6934 0.1051 0.055 Uiso 1 1 calc R U
C13 C 0.1065(3) 0.4952(3) 0.2006(2) 0.0435(5) Uani 1 1 d . .
H13A H 0.0749 0.5423 0.2564 0.052 Uiso 1 1 calc R U
C14 C 0.0649(3) 0.3365(3) 0.20805(19) 0.0355(4) Uani 1 1 d . .
H14A H 0.0021 0.2741 0.2683 0.043 Uiso 1 1 calc R U
C15 C -0.0841(2) -0.0214(2) 0.11617(16) 0.0302(4) Uani 1 1 d . .
C16 C -0.2039(3) -0.0022(3) 0.07500(18) 0.0354(4) Uani 1 1 d . .
H16A H -0.1877 0.0998 0.0563 0.042 Uiso 1 1 calc R U
C17 C -0.3402(3) -0.2604(3) 0.09291(18) 0.0398(5) Uani 1 1 d . .
H17A H -0.4290 -0.3651 0.0899 0.048 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
C17 S1 C15 89.50(11)
C17 N1 C16 109.6(2)
C2 C1 C6 120.9(2)
C2 C1 H1A 119.5
C6 C1 H1A 119.5
C3 C2 C1 120.6(2)
C3 C2 H2A 119.7
C1 C2 H2A 119.7
C2 C3 C4 119.2(2)
C2 C3 H3A 120.4
C4 C3 H3A 120.4
C5 C4 C3 120.4(2)
C5 C4 H4A 119.8
C3 C4 H4A 119.8
C4 C5 C6 121.1(2)
C4 C5 H5A 119.5
C6 C5 H5A 119.5
C5 C6 C1 117.8(2)
C5 C6 C7 124.31(18)
C1 C6 C7 117.65(19)
C8 C7 C6 129.86(19)
C8 C7 H7A 115.1
C6 C7 H7A 115.1
C7 C8 C15 121.78(19)
C7 C8 C9 122.93(19)
C15 C8 C9 115.25(18)
C14 C9 C10 119.0(2)
C14 C9 C8 121.18(19)
C10 C9 C8 119.83(19)
C11 C10 C9 120.3(2)
C11 C10 H10A 119.9
C9 C10 H10A 119.9
C12 C11 C10 120.3(2)
C12 C11 H11A 119.8
C10 C11 H11A 119.8
C11 C12 C13 120.6(2)
C11 C12 H12A 119.7
C13 C12 H12A 119.7
C14 C13 C12 119.5(2)
C14 C13 H13A 120.3
C12 C13 H13A 120.3
C13 C14 C9 120.4(2)
C13 C14 H14A 119.8
C9 C14 H14A 119.8
C16 C15 C8 128.13(19)
C16 C15 S1 108.40(15)
C8 C15 S1 123.47(16)
C15 C16 N1 116.9(2)
C15 C16 H16A 121.6
N1 C16 H16A 121.6
N1 C17 S1 115.57(18)
N1 C17 H17A 122.2
S1 C17 H17A 122.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C17 1.718(2)
S1 C15 1.727(2)
N1 C17 1.298(3)
N1 C16 1.374(3)
C1 C2 1.382(3)
C1 C6 1.395(3)
C1 H1A 0.9500
C2 C3 1.377(4)
C2 H2A 0.9500
C3 C4 1.389(3)
C3 H3A 0.9500
C4 C5 1.378(3)
C4 H4A 0.9500
C5 C6 1.393(3)
C5 H5A 0.9500
C6 C7 1.471(3)
C7 C8 1.345(3)
C7 H7A 0.9500
C8 C15 1.463(3)
C8 C9 1.492(3)
C9 C14 1.392(3)
C9 C10 1.394(3)
C10 C11 1.385(3)
C10 H10A 0.9500
C11 C12 1.364(4)
C11 H11A 0.9500
C12 C13 1.391(4)
C12 H12A 0.9500
C13 C14 1.387(3)
C13 H13A 0.9500
C14 H14A 0.9500
C15 C16 1.362(3)
C16 H16A 0.9500
C17 H17A 0.9500
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 C3 1.1(4)
C1 C2 C3 C4 -0.3(4)
C2 C3 C4 C5 -0.5(4)
C3 C4 C5 C6 0.5(4)
C4 C5 C6 C1 0.2(3)
C4 C5 C6 C7 175.0(2)
C2 C1 C6 C5 -1.0(3)
C2 C1 C6 C7 -176.2(2)
C5 C6 C7 C8 21.5(4)
C1 C6 C7 C8 -163.7(2)
C6 C7 C8 C15 -174.9(2)
C6 C7 C8 C9 7.3(4)
C7 C8 C9 C14 -107.3(3)
C15 C8 C9 C14 74.8(2)
C7 C8 C9 C10 70.5(3)
C15 C8 C9 C10 -107.4(2)
C14 C9 C10 C11 0.8(3)
C8 C9 C10 C11 -177.0(2)
C9 C10 C11 C12 0.7(3)
C10 C11 C12 C13 -1.1(4)
C11 C12 C13 C14 -0.1(3)
C12 C13 C14 C9 1.7(3)
C10 C9 C14 C13 -2.0(3)
C8 C9 C14 C13 175.8(2)
C7 C8 C15 C16 -169.6(2)
C9 C8 C15 C16 8.4(3)
C7 C8 C15 S1 10.5(3)
C9 C8 C15 S1 -171.53(16)
C17 S1 C15 C16 0.01(17)
C17 S1 C15 C8 179.93(18)
C8 C15 C16 N1 -179.9(2)
S1 C15 C16 N1 0.0(2)
C17 N1 C16 C15 -0.1(3)
C16 N1 C17 S1 0.1(3)
C15 S1 C17 N1 -0.06(19)
