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#$Date: 2023-05-05 04:17:41 +0300 (Fri, 05 May 2023) $
#$Revision: 283195 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/65/7246571.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_7246571
loop_
_publ_author_name
'Hosseinpoor, Saeed'
'Pourayoubi, Mehrdad'
'Abrishami, Mozhgan'
'Sobati, Marjan'
'Karimi Ahmadabad, Fatemeh'
'Sabbaghi, Fahimeh'
'Nečas, Marek'
'Dušek, Michal'
'Kučeráková, Monika'
'Kaur, Manpreet'
_publ_section_title
;
 Competing and directing interactions in new
 phosphoramide/thiophosphoramide structures: energy considerations and
 evidence for CH⋯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 ω-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/[σ²(Fo²)+(0.0377P)²+0.3432P] where P=(Fo²+2Fc²)/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 > 2σ(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_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   0.943
_shelx_estimated_absorpt_t_max   0.971
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
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
S1 S 0.19802(6) 0.53719(5) -0.02748(5) 0.02186(16) Uani 1 1 d . . . . .
P1 P 0.34535(6) 0.49876(5) 0.05848(5) 0.01612(15) Uani 1 1 d . . . . .
N1 N 0.4637(2) 0.59925(16) 0.06486(16) 0.0193(4) Uani 1 1 d . . . . .
H1A H 0.431594 0.666261 0.054211 0.023 Uiso 1 1 calc R U . . .
N2 N 0.4270(2) 0.38133(17) 0.03542(14) 0.0183(5) Uani 1 1 d . . . . .
H2A H 0.442254 0.336723 0.081850 0.022 Uiso 1 1 calc R U . . .
N3 N 0.3002(2) 0.47901(18) 0.16682(16) 0.0196(5) Uani 1 1 d . . . . .
H3A H 0.346130 0.519064 0.207307 0.023 Uiso 1 1 calc R U . . .
N4 N 0.8407(2) 0.66891(17) 0.06064(18) 0.0222(4) Uani 1 1 d . . . . .
N5 N 0.5727(3) 0.38598(19) -0.19758(16) 0.0271(5) Uani 1 1 d . . . . .
N6 N 0.0321(2) 0.25805(18) 0.18044(15) 0.0217(5) Uani 1 1 d . . . . .
C1 C 0.6093(2) 0.5914(2) 0.08516(17) 0.0180(5) Uani 1 1 d . . . . .
C2 C 0.7006(3) 0.6687(2) 0.04719(18) 0.0191(5) Uani 1 1 d . . . . .
H2B H 0.661337 0.724688 0.009450 0.023 Uiso 1 1 calc R U . . .
C3 C 0.8950(3) 0.5883(2) 0.1129(2) 0.0238(5) Uani 1 1 d . . . . .
H3B H 0.994531 0.585665 0.121730 0.029 Uiso 1 1 calc R U . . .
C4 C 0.8117(3) 0.5090(2) 0.1542(2) 0.0246(6) Uani 1 1 d . . . . .
H4B H 0.853908 0.453618 0.191275 0.029 Uiso 1 1 calc R U . . .
C5 C 0.6664(3) 0.5105(2) 0.14144(19) 0.0218(6) Uani 1 1 d . . . . .
H5B H 0.607330 0.457478 0.170405 0.026 Uiso 1 1 calc R U . . .
C6 C 0.4748(3) 0.34510(19) -0.05030(17) 0.0185(5) Uani 1 1 d . . . . .
C7 C 0.5191(3) 0.4183(2) -0.11736(18) 0.0222(6) Uani 1 1 d . . . . .
H7A H 0.511055 0.495237 -0.105710 0.027 Uiso 1 1 calc R U . . .
C8 C 0.5838(4) 0.2778(3) -0.2136(2) 0.0375(8) Uani 1 1 d . . . . .
H8A H 0.623695 0.254042 -0.269785 0.045 Uiso 1 1 calc R U . . .
C9 C 0.5398(4) 0.1994(2) -0.1518(2) 0.0394(8) Uani 1 1 d . . . . .
H9A H 0.547799 0.123027 -0.165941 0.047 Uiso 1 1 calc R U . . .
C10 C 0.4838(3) 0.2326(2) -0.06904(18) 0.0278(6) Uani 1 1 d . . . . .
H10A H 0.452128 0.179683 -0.025738 0.033 Uiso 1 1 calc R U . . .
C11 C 0.1980(2) 0.4064(2) 0.20185(17) 0.0168(5) Uani 1 1 d . . . . .
C12 C 0.1298(3) 0.3282(2) 0.14803(18) 0.0195(5) Uani 1 1 d . . . . .
H12A H 0.153528 0.324261 0.085069 0.023 Uiso 1 1 calc R U . . .
C13 C 0.0005(3) 0.2622(2) 0.26957(19) 0.0242(6) Uani 1 1 d . . . . .
H13A H -0.068392 0.212676 0.293114 0.029 Uiso 1 1 calc R U . . .
C14 C 0.0648(3) 0.3364(2) 0.32864(19) 0.0244(6) Uani 1 1 d . . . . .
H14A H 0.041370 0.336589 0.391742 0.029 Uiso 1 1 calc R U . . .
C15 C 0.1637(3) 0.4102(2) 0.29433(19) 0.0215(5) Uani 1 1 d . . . . .
H15A H 0.207467 0.462644 0.333427 0.026 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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
N2 P1 N1 109.18(10) . . ?
N2 P1 N3 101.02(11) . . ?
N1 P1 N3 103.02(11) . . ?
N2 P1 S1 114.22(9) . . ?
N1 P1 S1 110.25(8) . . ?
N3 P1 S1 118.17(8) . . ?
C1 N1 P1 128.41(16) . . ?
C1 N1 H1A 115.8 . . ?
P1 N1 H1A 115.8 . . ?
C6 N2 P1 126.97(17) . . ?
C6 N2 H2A 116.5 . . ?
P1 N2 H2A 116.5 . . ?
C11 N3 P1 128.05(18) . . ?
C11 N3 H3A 116.0 . . ?
P1 N3 H3A 116.0 . . ?
C2 N4 C3 117.4(2) . . ?
C8 N5 C7 118.1(2) . . ?
C13 N6 C12 118.3(2) . . ?
C2 C1 C5 118.1(2) . . ?
C2 C1 N1 118.4(2) . . ?
C5 C1 N1 123.4(2) . . ?
N4 C2 C1 123.8(2) . . ?
N4 C2 H2B 118.1 . . ?
C1 C2 H2B 118.1 . . ?
N4 C3 C4 122.6(2) . . ?
N4 C3 H3B 118.7 . . ?
C4 C3 H3B 118.7 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4B 120.1 . . ?
C5 C4 H4B 120.1 . . ?
C4 C5 C1 118.3(2) . . ?
C4 C5 H5B 120.9 . . ?
C1 C5 H5B 120.9 . . ?
C7 C6 C10 117.8(2) . . ?
C7 C6 N2 122.0(2) . . ?
C10 C6 N2 120.1(2) . . ?
N5 C7 C6 123.3(2) . . ?
N5 C7 H7A 118.4 . . ?
C6 C7 H7A 118.4 . . ?
N5 C8 C9 122.6(3) . . ?
N5 C8 H8A 118.7 . . ?
C9 C8 H8A 118.7 . . ?
C8 C9 C10 119.4(3) . . ?
C8 C9 H9A 120.3 . . ?
C10 C9 H9A 120.3 . . ?
C9 C10 C6 118.8(3) . . ?
C9 C10 H10A 120.6 . . ?
C6 C10 H10A 120.6 . . ?
C12 C11 C15 117.7(2) . . ?
C12 C11 N3 122.6(2) . . ?
C15 C11 N3 119.7(2) . . ?
N6 C12 C11 123.4(2) . . ?
N6 C12 H12A 118.3 . . ?
C11 C12 H12A 118.3 . . ?
N6 C13 C14 122.3(2) . . ?
N6 C13 H13A 118.8 . . ?
C14 C13 H13A 118.8 . . ?
C13 C14 C15 119.1(2) . . ?
C13 C14 H14A 120.5 . . ?
C15 C14 H14A 120.5 . . ?
C14 C15 C11 119.2(3) . . ?
C14 C15 H15A 120.4 . . ?
C11 C15 H15A 120.4 . . ?
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
S1 P1 1.9331(9) . ?
P1 N2 1.652(2) . ?
P1 N1 1.655(2) . ?
P1 N3 1.660(2) . ?
N1 C1 1.410(3) . ?
N1 H1A 0.8800 . ?
N2 C6 1.404(3) . ?
N2 H2A 0.8800 . ?
N3 C11 1.403(3) . ?
N3 H3A 0.8800 . ?
N4 C2 1.338(3) . ?
N4 C3 1.341(4) . ?
N5 C8 1.334(4) . ?
N5 C7 1.338(3) . ?
N6 C13 1.340(3) . ?
N6 C12 1.340(3) . ?
C1 C2 1.389(4) . ?
C1 C5 1.390(4) . ?
C2 H2B 0.9500 . ?
C3 C4 1.381(4) . ?
C3 H3B 0.9500 . ?
C4 C5 1.385(4) . ?
C4 H4B 0.9500 . ?
C5 H5B 0.9500 . ?
C6 C7 1.387(4) . ?
C6 C10 1.392(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.375(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.382(4) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C12 1.391(4) . ?
C11 C15 1.393(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.386(4) . ?
C13 H13A 0.9500 . ?
C14 C15 1.387(4) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A N4 0.88 2.17 3.038(3) 167.0 3_465 yes
N2 H2A N6 0.88 2.03 2.888(3) 164.7 3 yes
N3 H3A N5 0.88 1.96 2.838(3) 173.5 2_665 yes
