#------------------------------------------------------------------------------
#$Date: 2020-08-12 03:52:39 +0300 (Wed, 12 Aug 2020) $
#$Revision: 255242 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/88/1558828.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_1558828
loop_
_publ_author_name
'Imani, Zeynab'
'Mundlapati, V. Rao'
'Goldsztejn, Gildas'
'Brenner, Valerie'
'Gloaguen, Eric'
'Guillot, Régis'
'Baltaze, Jean-Pierre'
'Le Barbu-Debus, Katia'
'Robin, Sylvie'
'Zehnacker, Anne'
'MONS, Michel'
'Aitken, David J.'
_publ_section_title
;
 Conformation control through concurrent N--H···S and
 N--H···O=C hydrogen bonding and hyperconjugation
 effects
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC03339A
_journal_year                    2020
_chemical_formula_moiety         'C13 H16 N2 O3 S'
_chemical_formula_sum            'C13 H16 N2 O3 S'
_chemical_formula_weight         280.34
_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-2018/3
_audit_update_record
;
2020-02-20 deposited with the CCDC.	2020-08-11 downloaded from the CCDC.
;
_cell_angle_alpha                93.793(12)
_cell_angle_beta                 115.772(9)
_cell_angle_gamma                100.572(12)
_cell_formula_units_Z            2
_cell_length_a                   8.685(3)
_cell_length_b                   8.736(4)
_cell_length_c                   9.845(4)
_cell_measurement_reflns_used    9340
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      31.53
_cell_measurement_theta_min      2.33
_cell_volume                     652.2(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            52952
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         31.562
_diffrn_reflns_theta_min         2.329
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  0.9462
_exptl_absorpt_correction_T_min  0.9163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker APEX3'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_description       plate
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         4369
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0520P)²+0.1831P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0990
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3437
_reflns_number_total             4369
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc03339a2.cif
_cod_data_source_block           1
_cod_database_code               1558828
_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   0.971
_shelx_estimated_absorpt_t_max   0.993
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
C1 C 1.61601(15) 0.84144(15) 0.66960(13) 0.0163(2) Uani 1 1 d . . . . .
H1 H 1.527667 0.768327 0.679828 0.020 Uiso 1 1 calc R U . . .
C2 C 1.73800(16) 0.95599(15) 0.79376(14) 0.0184(2) Uani 1 1 d . . . . .
H2 H 1.731636 0.961178 0.887821 0.022 Uiso 1 1 calc R U . . .
C3 C 1.86879(16) 1.06259(15) 0.78083(14) 0.0182(2) Uani 1 1 d . . . . .
H3 H 1.951985 1.140442 0.865723 0.022 Uiso 1 1 calc R U . . .
C4 C 1.87720(16) 1.05465(15) 0.64287(14) 0.0180(2) Uani 1 1 d . . . . .
H4 H 1.966787 1.126946 0.633513 0.022 Uiso 1 1 calc R U . . .
C5 C 1.75482(15) 0.94114(15) 0.51848(13) 0.0175(2) Uani 1 1 d . . . . .
H5 H 1.760998 0.936725 0.424346 0.021 Uiso 1 1 calc R U . . .
C6 C 1.62273(14) 0.83344(14) 0.53075(13) 0.0136(2) Uani 1 1 d . . . . .
C7 C 1.49225(14) 0.71546(15) 0.39156(13) 0.0159(2) Uani 1 1 d . . . . .
H7A H 1.429647 0.770956 0.307008 0.019 Uiso 1 1 calc R U . . .
H7B H 1.553975 0.648852 0.357802 0.019 Uiso 1 1 calc R U . . .
C8 C 1.21508(14) 0.53927(13) 0.31178(12) 0.0120(2) Uani 1 1 d . . . . .
C9 C 0.92831(14) 0.37844(13) 0.26225(12) 0.0111(2) Uani 1 1 d . . . . .
C10 C 0.85371(15) 0.25473(14) 0.33540(13) 0.0144(2) Uani 1 1 d . . . . .
H10A H 0.785094 0.293795 0.382466 0.017 Uiso 1 1 calc R U . . .
H10B H 0.943285 0.205627 0.408057 0.017 Uiso 1 1 calc R U . . .
C11 C 0.89276(15) 0.25956(14) 0.12329(13) 0.0148(2) Uani 1 1 d . . . . .
H11A H 0.992824 0.211776 0.138511 0.018 Uiso 1 1 calc R U . . .
H11B H 0.850213 0.301797 0.025939 0.018 Uiso 1 1 calc R U . . .
C12 C 0.81960(13) 0.50524(13) 0.22502(12) 0.0114(2) Uani 1 1 d . . . . .
C13 C 0.67136(16) 0.67179(14) 0.04747(14) 0.0171(2) Uani 1 1 d . . . . .
H13A H 0.625643 0.672424 -0.062659 0.026 Uiso 1 1 calc R U . . .
H13B H 0.745834 0.776093 0.103640 0.026 Uiso 1 1 calc R U . . .
H13C H 0.572951 0.646396 0.072433 0.026 Uiso 1 1 calc R U . . .
N1 N 1.11098(12) 0.45655(11) 0.36323(10) 0.01221(18) Uani 1 1 d . . . . .
H10 H 1.154699 0.449412 0.461067 0.015 Uiso 1 1 calc R U . . .
N2 N 0.77506(12) 0.55337(11) 0.09062(10) 0.01295(19) Uani 1 1 d . . . . .
H2A H 0.808651 0.513168 0.026571 0.016 Uiso 1 1 calc R U . . .
O1 O 1.36837(10) 0.61842(10) 0.42984(9) 0.01528(17) Uani 1 1 d . . . . .
O2 O 1.17682(11) 0.54332(10) 0.17707(9) 0.01604(17) Uani 1 1 d . . . . .
O3 O 0.78196(11) 0.56237(10) 0.32199(9) 0.01813(18) Uani 1 1 d . . . . .
S1 S 0.71649(4) 0.13009(4) 0.14779(3) 0.01856(9) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0114 0.0062 '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 C1 C2 120.42(11) . . ?
C6 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C3 C2 C1 120.39(11) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.55(11) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.17(11) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.57(11) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.91(11) . . ?
C1 C6 C7 122.96(10) . . ?
C5 C6 C7 118.12(10) . . ?
O1 C7 C6 108.58(9) . . ?
O1 C7 H7A 110.0 . . ?
C6 C7 H7A 110.0 . . ?
O1 C7 H7B 110.0 . . ?
C6 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
O2 C8 N1 125.23(10) . . ?
O2 C8 O1 124.47(10) . . ?
N1 C8 O1 110.31(10) . . ?
N1 C9 C10 111.88(9) . . ?
N1 C9 C11 116.83(9) . . ?
C10 C9 C11 94.48(9) . . ?
N1 C9 C12 108.32(9) . . ?
C10 C9 C12 109.48(9) . . ?
C11 C9 C12 115.11(9) . . ?
C9 C10 S1 90.52(7) . . ?
C9 C10 H10A 113.6 . . ?
S1 C10 H10A 113.6 . . ?
C9 C10 H10B 113.5 . . ?
S1 C10 H10B 113.6 . . ?
H10A C10 H10B 110.8 . . ?
C9 C11 S1 89.95(7) . . ?
C9 C11 H11A 113.7 . . ?
S1 C11 H11A 113.7 . . ?
C9 C11 H11B 113.7 . . ?
S1 C11 H11B 113.7 . . ?
H11A C11 H11B 110.9 . . ?
O3 C12 N2 122.17(10) . . ?
O3 C12 C9 119.60(9) . . ?
N2 C12 C9 118.18(10) . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 N1 C9 122.00(9) . . ?
C8 N1 H10 119.0 . . ?
C9 N1 H10 119.0 . . ?
C12 N2 C13 121.10(10) . . ?
C12 N2 H2A 119.5 . . ?
C13 N2 H2A 119.5 . . ?
C8 O1 C7 116.42(9) . . ?
C10 S1 C11 75.76(6) . . ?
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
C1 C6 1.3912(17) . ?
C1 C2 1.3932(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.3882(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3893(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3905(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3983(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.5028(17) . ?
C7 O1 1.4417(14) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O2 1.2239(14) . ?
C8 N1 1.3428(15) . ?
C8 O1 1.3460(14) . ?
C9 N1 1.4534(15) . ?
C9 C10 1.5355(16) . ?
C9 C11 1.5403(16) . ?
C9 C12 1.5457(16) . ?
C10 S1 1.8333(13) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 S1 1.8446(13) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O3 1.2393(14) . ?
C12 N2 1.3286(14) . ?
C13 N2 1.4591(15) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N1 H10 0.8800 . ?
N2 H2A 0.8800 . ?
