Conformation control through concurrent N–H···S and N–H···O=C hydrogen bonding and hyperconjugation effects
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.; Chemical Science  (2020) –; doi:10.1039/D0SC03339A

data_1558828
_publ_section_title
;
 Conformation control through concurrent N--H&#x00B7;&#x00B7;&#x00B7;S and
 N--H&#x00B7;&#x00B7;&#x00B7;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       '\f and \w 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/[\s^2^(Fo^2^)+(0.0520P)^2^+0.1831P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(I)'
_cod_data_source_file            d0sc03339a2.cif
_cod_data_source_block           1
_cod_database_code               1558828
_shelx_estimated_absorpt_t_min   0.971
_shelx_estimated_absorpt_t_max   0.993
_shelx_res_checksum              15559