#------------------------------------------------------------------------------
#$Date: 2017-11-07 02:45:42 +0200 (Tue, 07 Nov 2017) $
#$Revision: 202696 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/28/4032894.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_4032894
loop_
_publ_author_name
'Seo, Boram'
'Kim, Hyunseok'
'Kim, Ya Gob'
'Baek, Yonghyeon'
'Um, Kyusik'
'Lee, Phil Ho'
_publ_section_title
;
 Synthesis of Bicyclic Isothiazoles through an Intramolecular
 Rhodium-Catalyzed Transannulation of Cyanothiadiazoles.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10574
_journal_page_last               10582
_journal_paper_doi               10.1021/acs.joc.7b02077
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C12 H9 N O2 S'
_chemical_formula_weight         231.26
_chemical_name_common            JBK-477
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 105.4655(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2740(4)
_cell_length_b                   11.8466(4)
_cell_length_c                   7.7264(2)
_cell_measurement_reflns_used    9086
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      28.1334
_cell_measurement_theta_min      2.4329
_cell_volume                     1082.78(6)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            21368
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.248
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1905
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0690
_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)+(0.1000P)²+1.1411P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1822
_refine_ls_wR_factor_ref         0.1914
_reflns_number_gt                1660
_reflns_number_total             1905
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b02077_si_001.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 4032893--4032894.cif.'
_cod_database_code               4032894
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
C C1 0.3310(3) 0.1213(3) 0.0514(4) 0.0535(8) Uani d . . 1
C C2 0.2885(3) 0.0037(3) 0.0510(5) 0.0680(10) Uani d . . 1
H H2A 0.2971 -0.0222 0.173 0.082 Uiso calc U R 1
H H2B 0.3305 -0.0466 -0.0067 0.082 Uiso calc U R 1
C C3 0.1651(3) 0.0053(3) -0.0516(5) 0.0666(9) Uani d . . 1
H H3A 0.1585 0.0246 -0.1759 0.08 Uiso calc U R 1
H H3B 0.1334 -0.0695 -0.0491 0.08 Uiso calc U R 1
C C4 0.1412(3) 0.1903(3) 0.0672(4) 0.0497(7) Uani d . . 1
C C5 0.2562(2) 0.2132(2) 0.0500(4) 0.0451(7) Uani d . . 1
C C6 0.3097(2) 0.3155(3) 0.0486(4) 0.0468(7) Uani d . . 1
C C7 0.2689(2) 0.4326(2) 0.0400(4) 0.0448(7) Uani d . . 1
C C8 0.3406(3) 0.5201(3) 0.1214(5) 0.0603(9) Uani d . . 1
H H8 0.4143 0.5039 0.1864 0.072 Uiso calc U R 1
C C9 0.3035(3) 0.6294(3) 0.1064(6) 0.0757(11) Uani d . . 1
H H9 0.3527 0.6868 0.16 0.091 Uiso calc U R 1
C C10 0.1942(3) 0.6559(3) 0.0129(6) 0.0753(11) Uani d . . 1
H H10 0.169 0.7302 0.0046 0.09 Uiso calc U R 1
C C11 0.1233(3) 0.5701(3) -0.0676(5) 0.0594(9) Uani d . . 1
H H11 0.0498 0.5874 -0.1322 0.071 Uiso calc U R 1
C C12 0.1579(2) 0.4601(3) -0.0554(4) 0.0474(7) Uani d . . 1
H H12 0.108 0.4035 -0.1102 0.057 Uiso calc U R 1
N N1 0.4353(2) 0.1482(3) 0.0481(4) 0.0645(8) Uani d . . 1
O O1 0.1011(2) 0.08584(19) 0.0237(3) 0.0629(7) Uani d . . 1
O O2 0.08477(19) 0.2565(2) 0.1248(4) 0.0635(7) Uani d . . 1
S S1 0.44509(7) 0.28707(8) 0.04464(13) 0.0649(4) Uani d . . 1
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
N1 C1 C5 116.1(3)
N1 C1 C2 124.4(3)
C5 C1 C2 119.5(3)
C1 C2 C3 107.0(3)
C1 C2 H2A 110.3
C3 C2 H2A 110.3
C1 C2 H2B 110.3
C3 C2 H2B 110.3
H2A C2 H2B 108.6
O1 C3 C2 111.8(3)
O1 C3 H3A 109.3
C2 C3 H3A 109.3
O1 C3 H3B 109.3
C2 C3 H3B 109.3
H3A C3 H3B 107.9
O2 C4 O1 118.9(3)
O2 C4 C5 124.7(3)
O1 C4 C5 116.3(3)
C6 C5 C1 111.4(3)
C6 C5 C4 129.1(3)
C1 C5 C4 119.2(3)
C5 C6 C7 132.3(3)
C5 C6 S1 107.2(2)
C7 C6 S1 120.5(2)
C8 C7 C12 118.2(3)
C8 C7 C6 120.9(3)
C12 C7 C6 120.9(3)
C9 C8 C7 120.6(3)
C9 C8 H8 119.7
C7 C8 H8 119.7
C8 C9 C10 121.0(3)
C8 C9 H9 119.5
C10 C9 H9 119.5
C11 C10 C9 118.6(3)
C11 C10 H10 120.7
C9 C10 H10 120.7
C12 C11 C10 121.8(3)
C12 C11 H11 119.1
C10 C11 H11 119.1
C11 C12 C7 119.9(3)
C11 C12 H12 120.1
C7 C12 H12 120.1
C1 N1 S1 108.4(2)
C4 O1 C3 120.3(3)
N1 S1 C6 96.93(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.325(4)
C1 C5 1.423(4)
C1 C2 1.487(5)
C2 C3 1.511(5)
C2 H2A 0.97
C2 H2B 0.97
C3 O1 1.453(4)
C3 H3A 0.97
C3 H3B 0.97
C4 O2 1.208(4)
C4 O1 1.341(4)
C4 C5 1.478(4)
C5 C6 1.379(4)
C6 C7 1.471(4)
C6 S1 1.704(3)
C7 C8 1.396(4)
C7 C12 1.403(4)
C8 C9 1.367(5)
C8 H8 0.93
C9 C10 1.379(6)
C9 H9 0.93
C10 C11 1.374(5)
C10 H10 0.93
C11 C12 1.366(4)
C11 H11 0.93
C12 H12 0.93
N1 S1 1.651(4)
