#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:58:23 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230678 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/64/7156497.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_7156497
loop_
_publ_author_name
'Dahiya, Anjali'
'Ali, Wajid'
'Alam, Tipu'
'Patel, Bhisma K.'
_publ_section_title
;
 A cascade synthesis of S-allyl benzoylcarbamothioates via Mumm-type
 rearrangement.
;
_journal_issue                   42
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7787
_journal_page_last               7791
_journal_paper_doi               10.1039/c8ob02293c
_journal_volume                  16
_journal_year                    2018
_chemical_formula_sum            'C21 H21 N O4 S'
_chemical_formula_weight         383.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-05-21 deposited with the CCDC.
2018-10-08 downloaded from the CCDC.
;
_cell_angle_alpha                73.896(14)
_cell_angle_beta                 89.385(10)
_cell_angle_gamma                80.113(11)
_cell_formula_units_Z            2
_cell_length_a                   5.2634(5)
_cell_length_b                   12.909(2)
_cell_length_c                   14.964(2)
_cell_measurement_reflns_used    1617
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4220
_cell_measurement_theta_min      3.6550
_cell_volume                     961.6(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0891
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6090
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.047
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_min         2.860
_exptl_absorpt_coefficient_mu    0.195
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3376
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.1253
_refine_ls_R_factor_gt           0.0786
_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)+3.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1960
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2129
_reflns_number_total             3376
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ob02293c2.cif
_cod_data_source_block           exp_4416
_cod_depositor_comments          'Adding full bibliography for 7156497.cif.'
_cod_database_code               7156497
_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.
;
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
S10 S 0.7594(3) 0.80340(12) 0.35469(10) 0.0482(4) Uani 1 1 d . .
O15 O 0.4512(7) 0.9505(3) 0.4137(3) 0.0560(11) Uani 1 1 d . .
O14 O 1.1404(7) 0.7496(3) 0.4871(3) 0.0585(11) Uani 1 1 d . .
N12 N 0.8128(8) 0.8795(3) 0.5027(3) 0.0419(10) Uani 1 1 d . .
H12 H 0.7596 0.9233 0.5357 0.050 Uiso 1 1 calc R U
O17 O 0.7425(9) 0.8144(4) 0.0526(3) 0.0733(14) Uani 1 1 d . .
O19 O 0.7336(11) 0.9505(4) 0.1176(3) 0.0873(17) Uani 1 1 d . .
C20 C 1.1706(10) 0.8131(4) 0.6199(4) 0.0435(13) Uani 1 1 d . .
C11 C 0.6546(10) 0.8877(4) 0.4273(4) 0.0423(12) Uani 1 1 d . .
C13 C 1.0434(10) 0.8111(4) 0.5320(4) 0.0446(13) Uani 1 1 d . .
C6 C 0.3513(11) 0.6040(5) 0.3448(4) 0.0530(15) Uani 1 1 d . .
H6 H 0.4657 0.6355 0.3713 0.064 Uiso 1 1 calc R U
C21 C 1.0747(11) 0.8851(5) 0.6710(4) 0.0548(15) Uani 1 1 d . .
H21 H 0.9227 0.9350 0.6512 0.066 Uiso 1 1 calc R U
C9 C 0.4773(10) 0.8483(5) 0.2747(4) 0.0464(13) Uani 1 1 d . .
H9A H 0.3275 0.8244 0.3068 0.056 Uiso 1 1 calc R U
H9B H 0.4427 0.9276 0.2524 0.056 Uiso 1 1 calc R U
C7 C 0.4420(11) 0.7135(5) 0.1841(4) 0.0557(16) Uani 1 1 d . .
H7 H 0.4758 0.6991 0.1272 0.067 Uiso 1 1 calc R U
C8 C 0.5276(10) 0.7998(5) 0.1927(4) 0.0487(14) Uani 1 1 d . .
C25 C 1.3934(11) 0.7385(5) 0.6520(5) 0.0611(17) Uani 1 1 d . .
H25 H 1.4585 0.6899 0.6183 0.073 Uiso 1 1 calc R U
C1 C 0.3026(10) 0.6347(5) 0.2470(4) 0.0472(13) Uani 1 1 d . .
C16 C 0.6762(12) 0.8621(6) 0.1178(4) 0.0604(17) Uani 1 1 d . .
C5 C 0.2221(12) 0.5251(5) 0.3996(5) 0.0638(18) Uani 1 1 d . .
H5 H 0.2610 0.5002 0.4633 0.077 Uiso 1 1 calc R U
C4 C 0.0402(12) 0.4829(5) 0.3632(5) 0.0640(18) Uani 1 1 d . .
H4 H -0.0502 0.4336 0.4022 0.077 Uiso 1 1 calc R U
C22 C 1.2047(12) 0.8825(5) 0.7510(4) 0.0606(16) Uani 1 1 d . .
H22 H 1.1426 0.9321 0.7842 0.073 Uiso 1 1 calc R U
C2 C 0.1218(12) 0.5911(5) 0.2120(5) 0.0640(17) Uani 1 1 d . .
H2 H 0.0842 0.6138 0.1482 0.077 Uiso 1 1 calc R U
C3 C -0.0088(12) 0.5138(5) 0.2684(5) 0.0680(19) Uani 1 1 d . .
H3 H -0.1273 0.4835 0.2425 0.082 Uiso 1 1 calc R U
C24 C 1.5204(13) 0.7346(6) 0.7323(5) 0.076(2) Uani 1 1 d . .
H24 H 1.6698 0.6835 0.7534 0.091 Uiso 1 1 calc R U
C23 C 1.4238(13) 0.8078(6) 0.7821(5) 0.0699(19) Uani 1 1 d . .
H23 H 1.5087 0.8059 0.8369 0.084 Uiso 1 1 calc R U
C18 C 0.8925(15) 0.8701(7) -0.0213(5) 0.094(3) Uani 1 1 d . .
H18A H 0.9183 0.8307 -0.0674 0.140 Uiso 1 1 calc R U
H18B H 1.0569 0.8734 0.0040 0.140 Uiso 1 1 calc R U
H18C H 0.8019 0.9430 -0.0494 0.140 Uiso 1 1 calc R U
C10 C 0.3650(17) 0.5302(7) 0.9802(6) 0.106(3) Uani 1 1 d . .
H10A H 0.3652 0.5463 0.9129 0.127 Uiso 1 1 calc R U
H10B H 0.3313 0.5995 0.9953 0.127 Uiso 1 1 calc R U
C12 C 0.1405(17) 0.4672(7) 1.0156(6) 0.108(3) Uani 1 1 d . .
H12A H 0.1530 0.4437 1.0831 0.129 Uiso 1 1 calc R U
H12B H 0.1645 0.4018 0.9944 0.129 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
C11 S10 C9 96.8(2) . .
C13 N12 C11 128.7(5) . .
C13 N12 H12 115.6 . .
C11 N12 H12 115.6 . .
C16 O17 C18 116.9(6) . .
C25 C20 C21 118.8(6) . .
C25 C20 C13 117.8(5) . .
C21 C20 C13 123.4(5) . .
O15 C11 N12 119.8(5) . .
O15 C11 S10 122.5(4) . .
N12 C11 S10 117.6(4) . .
O14 C13 N12 120.3(5) . .
O14 C13 C20 121.2(5) . .
N12 C13 C20 118.4(5) . .
C5 C6 C1 117.8(6) . .
C5 C6 H6 121.1 . .
C1 C6 H6 121.1 . .
C22 C21 C20 119.9(5) . .
C22 C21 H21 120.1 . .
C20 C21 H21 120.1 . .
C8 C9 S10 109.4(4) . .
C8 C9 H9A 109.8 . .
S10 C9 H9A 109.8 . .
C8 C9 H9B 109.8 . .
S10 C9 H9B 109.8 . .
H9A C9 H9B 108.2 . .
C8 C7 C1 132.5(6) . .
C8 C7 H7 113.7 . .
C1 C7 H7 113.7 . .
C7 C8 C16 120.7(6) . .
C7 C8 C9 124.8(5) . .
C16 C8 C9 114.4(5) . .
C24 C25 C20 121.4(7) . .
C24 C25 H25 119.3 . .
C20 C25 H25 119.3 . .
C2 C1 C6 118.8(5) . .
C2 C1 C7 120.2(6) . .
C6 C1 C7 120.9(5) . .
O19 C16 O17 122.8(6) . .
O19 C16 C8 123.0(6) . .
O17 C16 C8 114.3(6) . .
C4 C5 C6 122.3(6) . .
C4 C5 H5 118.9 . .
C6 C5 H5 118.9 . .
C5 C4 C3 119.7(6) . .
C5 C4 H4 120.1 . .
C3 C4 H4 120.1 . .
C23 C22 C21 120.6(6) . .
C23 C22 H22 119.7 . .
C21 C22 H22 119.7 . .
C1 C2 C3 122.3(6) . .
C1 C2 H2 118.9 . .
C3 C2 H2 118.9 . .
C4 C3 C2 118.9(6) . .
C4 C3 H3 120.5 . .
C2 C3 H3 120.5 . .
C25 C24 C23 119.2(6) . .
C25 C24 H24 120.4 . .
C23 C24 H24 120.4 . .
C22 C23 C24 120.2(6) . .
C22 C23 H23 119.9 . .
C24 C23 H23 119.9 . .
O17 C18 H18A 109.5 . .
O17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
O17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C10 C10 C12 115.3(9) 2_667 .
C10 C10 H10A 108.5 2_667 .
C12 C10 H10A 108.5 . .
C10 C10 H10B 108.5 2_667 .
C12 C10 H10B 108.5 . .
H10A C10 H10B 107.5 . .
C10 C12 C12 116.0(9) . 2_567
C10 C12 H12A 108.3 . .
C12 C12 H12A 108.3 2_567 .
C10 C12 H12B 108.3 . .
C12 C12 H12B 108.3 2_567 .
H12A C12 H12B 107.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S10 C11 1.763(5) .
S10 C9 1.825(5) .
O15 C11 1.208(6) .
O14 C13 1.221(6) .
N12 C13 1.369(6) .
N12 C11 1.378(6) .
N12 H12 0.8600 .
O17 C16 1.306(8) .
O17 C18 1.448(7) .
O19 C16 1.229(7) .
C20 C25 1.379(8) .
C20 C21 1.388(8) .
C20 C13 1.491(8) .
C6 C5 1.391(8) .
C6 C1 1.420(8) .
C6 H6 0.9300 .
C21 C22 1.375(8) .
C21 H21 0.9300 .
C9 C8 1.527(8) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C7 C8 1.309(8) .
C7 C1 1.472(7) .
C7 H7 0.9300 .
C8 C16 1.486(7) .
C25 C24 1.366(9) .
C25 H25 0.9300 .
C1 C2 1.362(8) .
C5 C4 1.365(9) .
C5 H5 0.9300 .
C4 C3 1.377(9) .
C4 H4 0.9300 .
C22 C23 1.362(9) .
C22 H22 0.9300 .
C2 C3 1.391(8) .
C2 H2 0.9300 .
C3 H3 0.9300 .
C24 C23 1.387(10) .
C24 H24 0.9300 .
C23 H23 0.9300 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C10 C10 1.536(17) 2_667
C10 C12 1.554(12) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C12 C12 1.577(17) 2_567
C12 H12A 0.9700 .
C12 H12B 0.9700 .
