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_1558827
_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         'C17 H21 N3 O4 S2'
_chemical_formula_sum            'C17 H21 N3 O4 S2'
_chemical_formula_weight         395.49
_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                66.73(6)
_cell_angle_beta                 84.29(5)
_cell_angle_gamma                75.73(5)
_cell_formula_units_Z            6
_cell_length_a                   11.823(11)
_cell_length_b                   14.91(2)
_cell_length_c                   17.77(3)
_cell_measurement_reflns_used    9806
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      67.45
_cell_measurement_theta_min      2.70
_cell_volume                     2789(7)
_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 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          neutron
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            30314
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.658
_diffrn_reflns_theta_max         67.658
_diffrn_reflns_theta_min         2.706
_exptl_absorpt_coefficient_mu    2.843
_exptl_absorpt_correction_T_max  0.9528
_exptl_absorpt_correction_T_min  0.7386
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker APEX3'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       needle
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.240
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     706
_refine_ls_number_reflns         9707
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0605
_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^)+(0.1152P)^2^+1.6099P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1656
_refine_ls_wR_factor_ref         0.1779
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7902
_reflns_number_total             9707
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc03339a2.cif
_cod_data_source_block           2
_cod_database_code               1558827
_shelx_estimated_absorpt_t_min   0.554
_shelx_estimated_absorpt_t_max   0.946
_shelx_res_checksum              55891