Competition among weak C–H⋯O/S/H interactions in the crystal structure of {(C2H5O)2P(S)}2N2C4H8 bis(thiophosphoramide): experimental/computational studies
Khorramaki, Maliheh; Pourayoubi, Mehrdad; Darugar, Vahidreza; Vakili, Mohammad; Nečas, Marek; Akbari, Mahmood; Maaza, Malik; RSC Advances 15 (2025) 22671–22681; doi:10.1039/D5RA01306B

data_7250613
_publ_section_title
;
 Competition among weak C--H&#x22EF;O/S/H interactions in the crystal
 structure of {(C2H5O)2P(S)}2N2C4H8 bis(thiophosphoramide):
 experimental/computational studies
;
_journal_issue                   28
_journal_name_full               'RSC Advances'
_journal_page_first              22671
_journal_page_last               22681
_journal_paper_doi               10.1039/D5RA01306B
_journal_volume                  15
_journal_year                    2025
_chemical_formula_sum            'C12 H28 N2 O4 P2 S2'
_chemical_formula_weight         390.42
_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
;
2025-05-14 deposited with the CCDC.	2025-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                84.974(5)
_cell_angle_beta                 77.633(5)
_cell_angle_gamma                87.946(5)
_cell_formula_units_Z            1
_cell_length_a                   6.8399(4)
_cell_length_b                   8.3288(6)
_cell_length_c                   8.5473(5)
_cell_measurement_reflns_used    3071
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.8870
_cell_measurement_theta_min      2.4300
_cell_volume                     473.72(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection
;
Rigaku CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)
MSCServDetCCD = {5.7.3.4}
;
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4327
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         2.448
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.466
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       block
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1725
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0311
_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/[\s^2^(Fo^2^)+(0.0428P)^2^+0.2172P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0860
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1493
_reflns_number_total             1725
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra01306b2.cif
_cod_data_source_block           mkh11_a
_cod_database_code               7250613
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.913
_shelx_estimated_absorpt_t_max   0.933
_shelx_res_checksum              14935