#------------------------------------------------------------------------------
#$Date: 2019-11-24 19:07:18 +0200 (Sun, 24 Nov 2019) $
#$Revision: 239122 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/57/1555792.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_1555792
loop_
_publ_author_name
'Seo, Boram'
'Kim, Ya Gob'
'Lee, Phil Ho'
_publ_section_title
;
 Synthesis of Isothiazole via the Rhodium-Catalyzed Transannulation of
 1,2,3-Thiadiazoles with Nitriles.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5050
_journal_page_last               5053
_journal_paper_doi               10.1021/acs.orglett.6b02499
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         C30H24N2O4S2
_chemical_formula_sum            'C30 H24 N2 O4 S2'
_chemical_formula_weight         540.63
_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-2013
_cell_angle_alpha                90
_cell_angle_beta                 92.7628(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.4528(3)
_cell_length_b                   14.3902(4)
_cell_length_c                   8.7251(3)
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.2556
_cell_measurement_theta_min      2.4101
_cell_volume                     1310.89(7)
_computing_cell_refinement       'Bruker APEX II'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker APEX II'
_computing_molecular_graphics    'SHELXL-2013 (Sheldrick, 2013)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.883
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measurement_device_type  multi-scan
_diffrn_measurement_method       'not measured'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.883
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            25532
_diffrn_reflns_point_group_measured_fraction_full 0.883
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.497
_diffrn_reflns_theta_min         1.951
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       needle
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.867
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2434
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1038
_refine_ls_R_factor_gt           0.0913
_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)+(0.1791P)²+1.3952P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2390
_refine_ls_wR_factor_ref         0.2587
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1914
_reflns_number_total             2434
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol6b02499_si_002.cif
_cod_data_source_block           SBR-2182
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1555792
_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   0.868
_shelx_estimated_absorpt_t_max   0.981
_shelxl_version_number           2013-4
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
C1 C 0.7455(4) 0.6971(3) -0.2627(4) 0.0445(8) Uani 1 1 d . .
H1 H 0.7754 0.7529 -0.2206 0.053 Uiso 1 1 calc R U
C2 C 0.6770(4) 0.6965(3) -0.4028(4) 0.0541(10) Uani 1 1 d . .
H2 H 0.6594 0.7520 -0.4541 0.065 Uiso 1 1 calc R U
C3 C 0.6347(4) 0.6131(4) -0.4661(5) 0.0610(12) Uani 1 1 d . .
H3 H 0.5912 0.6128 -0.5616 0.073 Uiso 1 1 calc R U
C4 C 0.6560(4) 0.5322(3) -0.3910(5) 0.0595(11) Uani 1 1 d . .
H4 H 0.6268 0.4768 -0.4352 0.071 Uiso 1 1 calc R U
C5 C 0.7217(4) 0.5308(3) -0.2473(4) 0.0509(9) Uani 1 1 d . .
H5 H 0.7333 0.4752 -0.1940 0.061 Uiso 1 1 calc R U
C6 C 0.7692(3) 0.6134(3) -0.1853(4) 0.0409(8) Uani 1 1 d . .
C7 C 0.8536(3) 0.6133(2) -0.0432(4) 0.0389(7) Uani 1 1 d . .
C8 C 0.8377(3) 0.5591(2) 0.0913(4) 0.0380(7) Uani 1 1 d . .
C9 C 0.9354(3) 0.5726(2) 0.1994(4) 0.0400(7) Uani 1 1 d . .
C10 C 0.7148(3) 0.5090(3) 0.1180(4) 0.0415(8) Uani 1 1 d . .
C11 C 0.6142(5) 0.3644(4) 0.1605(6) 0.0673(12) Uani 1 1 d . U
H11A H 0.5811 0.3840 0.2574 0.081 Uiso 1 1 calc R U
H11B H 0.5481 0.3743 0.0802 0.081 Uiso 1 1 calc R U
C13 C 0.9642(3) 0.5350(2) 0.3538(3) 0.0345(7) Uani 1 1 d . .
C14 C 1.0073(4) 0.5944(2) 0.4726(4) 0.0409(8) Uani 1 1 d . .
H14 H 1.0126 0.6579 0.4543 0.049 Uiso 1 1 calc R U
C15 C 0.9581(3) 0.4396(2) 0.3850(4) 0.0410(8) Uani 1 1 d . .
H15 H 0.9302 0.3988 0.3077 0.049 Uiso 1 1 calc R U
N1 N 0.9584(3) 0.6656(2) -0.0397(4) 0.0425(7) Uani 1 1 d . .
O1 O 0.6148(3) 0.5509(2) 0.1330(5) 0.0704(10) Uani 1 1 d . .
O2 O 0.7279(3) 0.4181(2) 0.1283(4) 0.0566(8) Uani 1 1 d . .
S1 S 1.03887(8) 0.65154(6) 0.12459(10) 0.0443(4) Uani 1 1 d . .
C12 C 0.6487(8) 0.2682(6) 0.1677(8) 0.105(2) Uiso 1 1 d . .
H12A H 0.7102 0.2552 0.0922 0.157 Uiso 1 1 calc R U
H12B H 0.5738 0.2307 0.1478 0.157 Uiso 1 1 calc R U
H12C H 0.6854 0.2541 0.2680 0.157 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
C2 C1 C6 119.5(4) .
C2 C1 H1 120.2 .
C6 C1 H1 120.2 .
C3 C2 C1 119.9(4) .
C3 C2 H2 120.0 .
C1 C2 H2 120.0 .
C4 C3 C2 120.8(4) .
C4 C3 H3 119.6 .
C2 C3 H3 119.6 .
C3 C4 C5 120.7(4) .
C3 C4 H4 119.7 .
C5 C4 H4 119.7 .
C6 C5 C4 119.1(4) .
C6 C5 H5 120.4 .
C4 C5 H5 120.4 .
C5 C6 C1 119.9(3) .
C5 C6 C7 120.7(3) .
C1 C6 C7 119.2(3) .
N1 C7 C8 114.8(3) .
N1 C7 C6 118.3(3) .
C8 C7 C6 126.8(3) .
C9 C8 C7 112.1(3) .
C9 C8 C10 125.2(3) .
C7 C8 C10 121.7(3) .
C8 C9 C13 133.8(3) .
C8 C9 S1 107.1(2) .
C13 C9 S1 119.1(3) .
O1 C10 O2 124.8(3) .
O1 C10 C8 121.5(3) .
O2 C10 C8 113.6(3) .
C12 C11 O2 108.4(5) .
C12 C11 H11A 110.0 .
O2 C11 H11A 110.0 .
C12 C11 H11B 110.0 .
O2 C11 H11B 110.0 .
H11A C11 H11B 108.4 .
C14 C13 C15 118.0(3) .
C14 C13 C9 119.9(3) .
C15 C13 C9 122.0(3) .
C15 C14 C13 121.1(3) 3_766
C15 C14 H14 119.5 3_766
C13 C14 H14 119.5 .
C14 C15 C13 120.9(3) 3_766
C14 C15 H15 119.5 3_766
C13 C15 H15 119.5 .
C7 N1 S1 109.8(2) .
C10 O2 C11 117.2(3) .
N1 S1 C9 96.21(16) .
C11 C12 H12A 109.5 .
C11 C12 H12B 109.5 .
H12A C12 H12B 109.5 .
C11 C12 H12C 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.386(5) .
C1 C6 1.398(5) .
C1 H1 0.9300 .
C2 C3 1.385(7) .
C2 H2 0.9300 .
C3 C4 1.349(7) .
C3 H3 0.9300 .
C4 C5 1.401(5) .
C4 H4 0.9300 .
C5 C6 1.389(5) .
C5 H5 0.9300 .
C6 C7 1.487(4) .
C7 N1 1.328(5) .
C7 C8 1.426(4) .
C8 C9 1.370(4) .
C8 C10 1.502(5) .
C9 C13 1.469(4) .
C9 S1 1.719(4) .
C10 O1 1.219(5) .
C10 O2 1.317(5) .
C11 C12 1.432(9) .
C11 O2 1.457(6) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C13 C14 1.401(4) .
C13 C15 1.402(5) .
C14 C15 1.368(5) 3_766
C14 H14 0.9300 .
C15 C14 1.368(5) 3_766
C15 H15 0.9300 .
N1 S1 1.639(3) .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
