Competing and directing interactions in new phosphoramide/thiophosphoramide structures: energy considerations and evidence for CH⋯HC contacts and aliphatic–aromatic stacking
Hosseinpoor, Saeed; Pourayoubi, Mehrdad; Abrishami, Mozhgan; Sobati, Marjan; Karimi Ahmadabad, Fatemeh; Sabbaghi, Fahimeh; Nečas, Marek; Dušek, Michal; Kučeráková, Monika; Kaur, Manpreet; CrystEngComm 25 (2023) 2557–2569; doi:10.1039/D3CE00204G

data_7246571
_publ_section_title
;
 Competing and directing interactions in new
 phosphoramide/thiophosphoramide structures: energy considerations and
 evidence for CH&#x22EF;HC contacts and aliphatic--aromatic stacking
;
_journal_issue                   17
_journal_name_full               CrystEngComm
_journal_page_first              2557
_journal_page_last               2569
_journal_paper_doi               10.1039/D3CE00204G
_journal_volume                  25
_journal_year                    2023
_chemical_formula_sum            'C15 H15 N6 P S'
_chemical_formula_weight         342.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-09-18 deposited with the CCDC.	2023-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4456(2)
_cell_length_b                   12.1063(2)
_cell_length_c                   14.6424(3)
_cell_measurement_reflns_used    7478
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.6500
_cell_measurement_theta_min      3.8900
_cell_volume                     1674.38(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection
;
Rigaku CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)
MSCServDetCCD = {5.7.3.4}
;
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'AFC11 (Right): Eulerian 3 circle CCD'
_diffrn_measurement_method       'Profile data from \w-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9054
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.344
_diffrn_reflns_theta_min         3.069
_diffrn_source                   'Rotating Anode MicroMax-007HF DW 1.2 kW'
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85058
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1337 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2985
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0246
_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^)+(0.0377P)^2^+0.3432P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0628
_refine_ls_wR_factor_ref         0.0636
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_full    0.952
_reflns_Friedel_fraction_max     0.953
_reflns_number_gt                2917
_reflns_number_total             2985
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00204g2.cif
_cod_data_source_block           mpsab
_cod_depositor_comments
'Adding full bibliography for 7246569--7246573.cif.'
_cod_database_code               7246571
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.943
_shelx_estimated_absorpt_t_max   0.971
_shelx_res_checksum              79419
_shelx_hkl_checksum              2064