#------------------------------------------------------------------------------
#$Date: 2020-06-18 02:48:28 +0300 (Thu, 18 Jun 2020) $
#$Revision: 253220 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/83/1558332.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_1558332
loop_
_publ_author_name
'Sinclair, Geoffrey S.'
'Kukor, Andrew J.'
'Imperial, Kevin Karl G.'
'Schipper, Derek J.'
_publ_section_title
;
 Transition-Metal-Free ipso-Arylative Condensation
;
_journal_name_full               Macromolecules
_journal_paper_doi               10.1021/acs.macromol.0c00726
_journal_year                    2020
_chemical_formula_moiety         'C20 H16 N2 O S2'
_chemical_formula_sum            'C20 H16 N2 O S2'
_chemical_formula_weight         364.47
_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
_cell_angle_alpha                115.5107(10)
_cell_angle_beta                 101.2094(16)
_cell_angle_gamma                106.8613(11)
_cell_formula_units_Z            2
_cell_length_a                   9.7982(2)
_cell_length_b                   9.8590(2)
_cell_length_c                   11.1142(3)
_cell_measurement_reflns_used    899
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      1.5
_cell_volume                     861.61(4)
_computing_cell_refinement       'Bruker APEX II'
_computing_data_collection       'Bruker KAPPA APEXII'
_computing_data_reduction        'Bruker APEX II'
_computing_molecular_graphics    Mercury
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       'Omega and Phi scan '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17393
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.993
_diffrn_reflns_theta_min         2.329
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  90
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_T_max  0.745658
_exptl_absorpt_correction_T_min  0.673612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       needle
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.005
_refine_diff_density_max         1.226
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.354
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4164
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.354
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0588
_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)+(0.0368P)²+0.4399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1349
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2876
_reflns_number_total             4164
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ma0c00726_si_001.cif
_cod_data_source_block           twin4a
_cod_original_cell_volume        861.61(3)
_cod_database_code               1558332
_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   0.905
_shelx_estimated_absorpt_t_max   0.998
_shelxl_version_number           2014-3
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 0.52122(8) 0.12161(9) 0.30899(7) 0.0361(2) Uani 1 1 d . . . . .
S2 S 0.45088(9) 0.36215(9) 0.71258(8) 0.0379(2) Uani 1 1 d . . . . .
N1 N 0.3489(3) 0.3160(3) 0.4653(2) 0.0363(5) Uani 1 1 d . . . . .
N2 N 0.6448(3) 0.1934(3) 0.5681(3) 0.0375(6) Uani 1 1 d . . . . .
O1 O 0.3252(3) 0.2689(3) 0.3330(2) 0.0632(7) Uani 1 1 d . . . . .
C1 C 0.4475(3) 0.2890(3) 0.5421(3) 0.0331(6) Uani 1 1 d . . . . .
C2 C 0.3125(3) 0.4306(3) 0.6764(3) 0.0328(6) Uani 1 1 d . . . . .
C3 C 0.2704(3) 0.3981(3) 0.5396(3) 0.0348(6) Uani 1 1 d . . . . .
C4 C 0.6682(3) 0.0648(3) 0.3470(3) 0.0318(6) Uani 1 1 d . . . . .
C5 C 0.7195(3) 0.1130(3) 0.4894(3) 0.0354(6) Uani 1 1 d . . . . .
C6 C 0.5398(3) 0.2070(3) 0.4861(3) 0.0349(6) Uani 1 1 d . . . . .
C7 C 0.1567(4) 0.4309(4) 0.4597(3) 0.0461(8) Uani 1 1 d . . . . .
H7A H 0.1556 0.3916 0.3639 0.069 Uiso 1 1 calc R U . . .
H7B H 0.0566 0.3744 0.4560 0.069 Uiso 1 1 calc R U . . .
H7C H 0.1844 0.5479 0.5076 0.069 Uiso 1 1 calc R U . . .
C8 C 0.8412(4) 0.0861(4) 0.5670(3) 0.0454(8) Uani 1 1 d . . . . .
H8A H 0.8521 0.1336 0.6659 0.068 Uiso 1 1 calc R U . . .
H8B H 0.8133 -0.0306 0.5243 0.068 Uiso 1 1 calc R U . . .
H8C H 0.9367 0.1381 0.5607 0.068 Uiso 1 1 calc R U . . .
C9 C 0.2590(3) 0.5138(3) 0.7912(3) 0.0341(6) Uani 1 1 d . . . . .
C10 C 0.2557(3) 0.4701(4) 0.8946(3) 0.0431(7) Uani 1 1 d . . . . .
H10A H 0.2842 0.3861 0.8892 0.052 Uiso 1 1 calc R U . . .
C11 C 0.2108(4) 0.5500(4) 1.0048(4) 0.0511(8) Uani 1 1 d . . . . .
H11A H 0.2092 0.5196 1.0732 0.061 Uiso 1 1 calc R U . . .
C12 C 0.1684(4) 0.6740(4) 1.0147(4) 0.0533(9) Uani 1 1 d . . . . .
H12A H 0.1382 0.7276 1.0894 0.064 Uiso 1 1 calc R U . . .
C13 C 0.1707(4) 0.7189(4) 0.9130(4) 0.0497(8) Uani 1 1 d . . . . .
H13A H 0.1420 0.8030 0.9192 0.060 Uiso 1 1 calc R U . . .
C14 C 0.2158(3) 0.6391(4) 0.8019(3) 0.0417(7) Uani 1 1 d . . . . .
H14A H 0.2170 0.6700 0.7338 0.050 Uiso 1 1 calc R U . . .
C15 C 0.7222(3) -0.0155(3) 0.2313(3) 0.0323(6) Uani 1 1 d . . . . .
C16 C 0.6207(3) -0.1165(4) 0.0883(3) 0.0376(7) Uani 1 1 d . . . . .
H16A H 0.5170 -0.1402 0.0666 0.045 Uiso 1 1 calc R U . . .
C17 C 0.6724(4) -0.1812(4) -0.0206(3) 0.0422(7) Uani 1 1 d . . . . .
H17A H 0.6033 -0.2476 -0.1151 0.051 Uiso 1 1 calc R U . . .
C18 C 0.8254(4) -0.1488(4) 0.0088(3) 0.0441(7) Uani 1 1 d . . . . .
H18A H 0.8597 -0.1927 -0.0654 0.053 Uiso 1 1 calc R U . . .
C19 C 0.9270(4) -0.0508(4) 0.1491(3) 0.0436(7) Uani 1 1 d . . . . .
H19A H 1.0303 -0.0293 0.1696 0.052 Uiso 1 1 calc R U . . .
C20 C 0.8766(3) 0.0163(4) 0.2604(3) 0.0373(6) Uani 1 1 d . . . . .
H20A H 0.9463 0.0827 0.3547 0.045 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
C6 S1 C4 88.92(13) . . ?
C1 S2 C2 90.66(13) . . ?
O1 N1 C1 123.0(2) . . ?
O1 N1 C3 122.5(2) . . ?
C1 N1 C3 114.5(2) . . ?
C6 N2 C5 110.4(2) . . ?
N1 C1 C6 123.3(2) . . ?
N1 C1 S2 112.10(19) . . ?
C6 C1 S2 124.6(2) . . ?
C3 C2 C9 129.5(2) . . ?
C3 C2 S2 111.5(2) . . ?
C9 C2 S2 119.0(2) . . ?
C2 C3 N1 111.3(2) . . ?
C2 C3 C7 131.3(3) . . ?
N1 C3 C7 117.5(2) . . ?
C5 C4 C15 131.1(2) . . ?
C5 C4 S1 110.2(2) . . ?
C15 C4 S1 118.6(2) . . ?
C4 C5 N2 114.8(2) . . ?
C4 C5 C8 128.2(3) . . ?
N2 C5 C8 116.9(2) . . ?
N2 C6 C1 121.7(2) . . ?
N2 C6 S1 115.7(2) . . ?
C1 C6 S1 122.6(2) . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 118.4(3) . . ?
C14 C9 C2 121.6(3) . . ?
C10 C9 C2 120.0(2) . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 H10A 119.7 . . ?
C9 C10 H10A 119.7 . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11A 119.7 . . ?
C10 C11 H11A 119.7 . . ?
C11 C12 C13 119.6(3) . . ?
C11 C12 H12A 120.2 . . ?
C13 C12 H12A 120.2 . . ?
C12 C13 C14 120.2(3) . . ?
C12 C13 H13A 119.9 . . ?
C14 C13 H13A 119.9 . . ?
C13 C14 C9 120.6(3) . . ?
C13 C14 H14A 119.7 . . ?
C9 C14 H14A 119.7 . . ?
C20 C15 C16 118.2(3) . . ?
C20 C15 C4 121.1(3) . . ?
C16 C15 C4 120.6(2) . . ?
C17 C16 C15 120.9(3) . . ?
C17 C16 H16A 119.6 . . ?
C15 C16 H16A 119.6 . . ?
C16 C17 C18 120.7(3) . . ?
C16 C17 H17A 119.6 . . ?
C18 C17 H17A 119.6 . . ?
C19 C18 C17 119.4(3) . . ?
C19 C18 H18A 120.3 . . ?
C17 C18 H18A 120.3 . . ?
C18 C19 C20 120.6(3) . . ?
C18 C19 H19A 119.7 . . ?
C20 C19 H19A 119.7 . . ?
C19 C20 C15 120.3(3) . . ?
C19 C20 H20A 119.9 . . ?
C15 C20 H20A 119.9 . . ?
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 C6 1.721(3) . ?
S1 C4 1.733(3) . ?
S2 C1 1.702(3) . ?
S2 C2 1.735(3) . ?
N1 O1 1.284(3) . ?
N1 C1 1.326(3) . ?
N1 C3 1.401(3) . ?
N2 C6 1.314(3) . ?
N2 C5 1.384(3) . ?
C1 C6 1.438(4) . ?
C2 C3 1.358(4) . ?
C2 C9 1.477(4) . ?
C3 C7 1.485(4) . ?
C4 C5 1.374(4) . ?
C4 C15 1.480(4) . ?
C5 C8 1.488(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C14 1.385(4) . ?
C9 C10 1.393(4) . ?
C10 C11 1.377(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.369(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.382(5) . ?
C12 H12A 0.9300 . ?
C13 C14 1.384(4) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 C20 1.393(4) . ?
C15 C16 1.398(4) . ?
C16 C17 1.374(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.378(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.377(4) . ?
C18 H18A 0.9300 . ?
C19 C20 1.391(4) . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?
