#------------------------------------------------------------------------------
#$Date: 2020-07-01 02:21:34 +0300 (Wed, 01 Jul 2020) $
#$Revision: 253579 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/85/4038536.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_4038536
loop_
_publ_author_name
'Xiong, Wei'
'Zhang, Shengjun'
'Li, Huijun'
'Zhang, Zhifeng'
'Xu, Tongyu'
_publ_section_title
;
 Pd-Catalyzed Decarboxylative Cycloaddition of Vinylethylene Carbonates
 with Isothiocyanates.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00243
_journal_year                    2020
_chemical_formula_moiety         'C17 H15 N O S'
_chemical_formula_sum            'C17 H15 N O S'
_chemical_formula_weight         281.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 112.258(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5914(19)
_cell_length_b                   16.819(3)
_cell_length_c                   9.9640(19)
_cell_measurement_reflns_used    2563
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.86
_cell_measurement_theta_min      2.51
_cell_volume                     1487.6(5)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.982
_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  0.0247
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7262
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.095
_diffrn_reflns_theta_min         2.511
_exptl_absorpt_coefficient_mu    0.212
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.354
_exptl_crystal_size_mid          0.268
_exptl_crystal_size_min          0.149
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0364
_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)+(0.0399P)²+0.3613P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0973
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2091
_reflns_number_total             2634
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00243_si_002.cif
_cod_data_source_block           xb2545_0m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4038536
_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   0.929
_shelx_estimated_absorpt_t_max   0.969
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
S1 S 0.80037(6) 0.08786(3) 0.11104(6) 0.0645(2) Uani 1 1 d . . . . .
N1 N 0.57932(15) 0.13835(8) 0.19471(15) 0.0414(3) Uani 1 1 d . . . . .
O1 O 0.61609(16) 0.00957(7) 0.19900(16) 0.0626(4) Uani 1 1 d . . . . .
C1 C 0.59062(19) 0.22048(9) 0.16225(18) 0.0405(4) Uani 1 1 d . . . . .
C2 C 0.5378(2) 0.24428(12) 0.0195(2) 0.0543(5) Uani 1 1 d . . . . .
H2 H 0.4964 0.2073 -0.0544 0.065 Uiso 1 1 calc R U . . .
C3 C 0.5464(2) 0.32316(14) -0.0131(2) 0.0678(6) Uani 1 1 d . . . . .
H3 H 0.5118 0.3395 -0.1094 0.081 Uiso 1 1 calc R U . . .
C4 C 0.6059(3) 0.37751(13) 0.0958(3) 0.0688(6) Uani 1 1 d . . . . .
H4 H 0.6116 0.4307 0.0731 0.083 Uiso 1 1 calc R U . . .
C5 C 0.6571(2) 0.35420(12) 0.2378(2) 0.0631(6) Uani 1 1 d . . . . .
H5 H 0.6969 0.3916 0.3112 0.076 Uiso 1 1 calc R U . . .
C6 C 0.6499(2) 0.27515(10) 0.2723(2) 0.0501(5) Uani 1 1 d . . . . .
H6 H 0.6846 0.2590 0.3687 0.060 Uiso 1 1 calc R U . . .
C7 C 0.6607(2) 0.08041(10) 0.16794(19) 0.0474(4) Uani 1 1 d . . . . .
C8 C 0.4857(2) 0.01874(11) 0.2357(2) 0.0564(5) Uani 1 1 d . . . . .
H8A H 0.4979 -0.0109 0.3229 0.068 Uiso 1 1 calc R U . . .
H8B H 0.3961 -0.0003 0.1574 0.068 Uiso 1 1 calc R U . . .
C9 C 0.47255(19) 0.10835(9) 0.26035(19) 0.0429(4) Uani 1 1 d . . . . .
C10 C 0.3176(2) 0.14193(12) 0.1790(2) 0.0528(5) Uani 1 1 d . . . . .
H10 H 0.3118 0.1967 0.1647 0.063 Uiso 1 1 calc R U . . .
C11 C 0.1921(3) 0.10345(16) 0.1268(3) 0.0862(8) Uani 1 1 d . . . . .
H11A H 0.1911 0.0486 0.1379 0.103 Uiso 1 1 calc R U . . .
H11B H 0.1026 0.1306 0.0782 0.103 Uiso 1 1 calc R U . . .
C12 C 0.5325(2) 0.12935(10) 0.42158(19) 0.0443(4) Uani 1 1 d . . . . .
C13 C 0.6783(2) 0.10840(12) 0.5105(2) 0.0578(5) Uani 1 1 d . . . . .
H13 H 0.7387 0.0811 0.4716 0.069 Uiso 1 1 calc R U . . .
C14 C 0.7347(3) 0.12772(14) 0.6563(2) 0.0674(6) Uani 1 1 d . . . . .
H14 H 0.8324 0.1131 0.7150 0.081 Uiso 1 1 calc R U . . .
C15 C 0.6474(3) 0.16831(13) 0.7145(2) 0.0704(7) Uani 1 1 d . . . . .
H15 H 0.6860 0.1817 0.8123 0.084 Uiso 1 1 calc R U . . .
C16 C 0.5040(3) 0.18899(13) 0.6291(3) 0.0713(6) Uani 1 1 d . . . . .
H16 H 0.4445 0.2164 0.6689 0.086 Uiso 1 1 calc R U . . .
C17 C 0.4462(2) 0.16945(11) 0.4835(2) 0.0579(5) Uani 1 1 d . . . . .
H17 H 0.3477 0.1835 0.4264 0.070 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'
O O 0.0106 0.0060 '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
C7 N1 C1 123.93(14) . . ?
C7 N1 C9 112.91(14) . . ?
C1 N1 C9 123.15(13) . . ?
C7 O1 C8 110.32(13) . . ?
C2 C1 C6 120.51(16) . . ?
C2 C1 N1 118.96(15) . . ?
C6 C1 N1 120.51(15) . . ?
C1 C2 C3 119.55(19) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 120.08(19) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.52(19) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.27(18) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
N1 C7 O1 109.90(15) . . ?
N1 C7 S1 128.77(14) . . ?
O1 C7 S1 121.30(13) . . ?
O1 C8 C9 106.08(14) . . ?
O1 C8 H8A 110.5 . . ?
C9 C8 H8A 110.5 . . ?
O1 C8 H8B 110.5 . . ?
C9 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
N1 C9 C10 109.69(14) . . ?
N1 C9 C12 109.52(13) . . ?
C10 C9 C12 112.38(14) . . ?
N1 C9 C8 98.60(13) . . ?
C10 C9 C8 113.85(15) . . ?
C12 C9 C8 111.89(15) . . ?
C11 C10 C9 127.5(2) . . ?
C11 C10 H10 116.3 . . ?
C9 C10 H10 116.3 . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
C17 C12 C13 117.94(18) . . ?
C17 C12 C9 122.12(17) . . ?
C13 C12 C9 119.94(16) . . ?
C14 C13 C12 120.6(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 120.2(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 119.9(2) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.2(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 121.0(2) . . ?
C12 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
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 C7 1.6456(19) . ?
N1 C7 1.337(2) . ?
N1 C1 1.432(2) . ?
N1 C9 1.496(2) . ?
O1 C7 1.341(2) . ?
O1 C8 1.439(2) . ?
C1 C2 1.376(2) . ?
C1 C6 1.378(2) . ?
C2 C3 1.376(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C9 1.540(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.507(3) . ?
C9 C12 1.529(2) . ?
C10 C11 1.290(3) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9300 . ?
C11 H11B 0.9300 . ?
C12 C17 1.381(2) . ?
C12 C13 1.388(3) . ?
C13 C14 1.384(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.368(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.360(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 C1 C2 69.9(2) . . . . ?
C9 N1 C1 C2 -109.11(18) . . . . ?
C7 N1 C1 C6 -111.83(19) . . . . ?
C9 N1 C1 C6 69.2(2) . . . . ?
C6 C1 C2 C3 1.0(3) . . . . ?
N1 C1 C2 C3 179.30(17) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C2 C1 C6 C5 -0.7(3) . . . . ?
N1 C1 C6 C5 -178.95(16) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C1 N1 C7 O1 -174.90(15) . . . . ?
C9 N1 C7 O1 4.2(2) . . . . ?
C1 N1 C7 S1 7.1(3) . . . . ?
C9 N1 C7 S1 -173.82(13) . . . . ?
C8 O1 C7 N1 6.1(2) . . . . ?
C8 O1 C7 S1 -175.71(13) . . . . ?
C7 O1 C8 C9 -13.4(2) . . . . ?
C7 N1 C9 C10 -130.70(16) . . . . ?
C1 N1 C9 C10 48.4(2) . . . . ?
C7 N1 C9 C12 105.52(16) . . . . ?
C1 N1 C9 C12 -75.41(19) . . . . ?
C7 N1 C9 C8 -11.46(18) . . . . ?
C1 N1 C9 C8 167.61(15) . . . . ?
O1 C8 C9 N1 14.06(18) . . . . ?
O1 C8 C9 C10 130.13(16) . . . . ?
O1 C8 C9 C12 -101.09(17) . . . . ?
N1 C9 C10 C11 129.7(2) . . . . ?
C12 C9 C10 C11 -108.2(2) . . . . ?
C8 C9 C10 C11 20.3(3) . . . . ?
N1 C9 C12 C17 126.81(17) . . . . ?
C10 C9 C12 C17 4.6(2) . . . . ?
C8 C9 C12 C17 -124.92(18) . . . . ?
N1 C9 C12 C13 -52.8(2) . . . . ?
C10 C9 C12 C13 -175.02(16) . . . . ?
C8 C9 C12 C13 55.4(2) . . . . ?
C17 C12 C13 C14 -0.3(3) . . . . ?
C9 C12 C13 C14 179.33(16) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C13 C14 C15 C16 0.7(3) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C13 C12 C17 C16 0.8(3) . . . . ?
C9 C12 C17 C16 -178.85(17) . . . . ?
C15 C16 C17 C12 -0.5(3) . . . . ?
