#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/55/2215542.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2215542
loop_
_publ_author_name
'Wan, Rong'
'Han, Feng'
'Zhang, Jin-jun'
'Yin, Li-he'
'Wang, Jin-tang'
_publ_section_title
;(S)-Diethyl
 {(4-fluorophenyl)[5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-ylamino]methyl}phosphonate
;
_journal_coeditor_code           HK2321
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4158
_journal_page_last               o4158
_journal_paper_doi               10.1107/S1600536807046521
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C20 H23 F N3 O4 P S'
_chemical_formula_moiety         'C20 H23 F N3 O4 P S'
_chemical_formula_sum            'C20 H23 F N3 O4 P S'
_chemical_formula_weight         451.44
_chemical_melting_point          465
_chemical_name_systematic
;
(S)-Diethyl {(4-fluorophenyl)[5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-
ylamino]methyl}phosphonate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                110.44(3)
_cell_angle_beta                 98.80(3)
_cell_angle_gamma                100.58(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4140(19)
_cell_length_b                   10.227(2)
_cell_length_c                   12.923(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     1113.7(5)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Siemens, 1996)'
_computing_publication_material  'SHELXTL (Siemens, 1996)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4656
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         1.73
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  0.9505
_exptl_absorpt_correction_T_min  0.9271
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.316
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.823
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4374
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.828
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.088P)²+2.5493P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1568
_reflns_number_gt                3276
_reflns_number_total             4374
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2321.cif
_cod_data_source_block           I
_cod_database_code               2215542
_cod_database_fobs_code          2215542
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P 0.43635(9) 0.67087(8) -0.10499(7) 0.0491(2) Uani d . 1 . .
S S 0.87296(9) 0.75456(8) 0.24611(7) 0.0517(2) Uani d . 1 . .
F F 0.9354(3) 0.4665(3) -0.3671(2) 0.1057(9) Uani d . 1 . .
N N1 0.6691(3) 0.7228(3) 0.0607(2) 0.0522(6) Uani d . 1 . .
H H1 0.6079 0.6613 0.0747 0.063 Uiso calc R 1 . .
N N2 0.8756(3) 0.9250(3) 0.1405(2) 0.0606(7) Uani d . 1 . .
N N3 0.9991(3) 0.9880(3) 0.2313(2) 0.0616(7) Uani d . 1 . .
O O1 0.3723(3) 0.7941(3) -0.0351(2) 0.0662(6) Uani d . 1 A .
O O2 0.4072(3) 0.6740(2) -0.22638(19) 0.0637(6) Uani d . 1 A .
O O3 0.3799(2) 0.5289(2) -0.1037(2) 0.0634(6) Uani d . 1 A .
O O4 1.4759(3) 1.0977(3) 0.6845(2) 0.0969(10) Uani d . 1 . .
C C1 0.1394(13) 0.7103(15) 0.0092(13) 0.100(4) Uani d P 0.66(2) A 1
H H1A 0.1483 0.6129 -0.0121 0.150 Uiso calc PR 0.66(2) A 1
H H1B 0.0362 0.7101 -0.0028 0.150 Uiso calc PR 0.66(2) A 1
H H1C 0.1875 0.7645 0.0880 0.150 Uiso calc PR 0.66(2) A 1
C C1' 0.146(4) 0.794(6) 0.024(3) 0.102(17) Uani d P 0.34(2) A 2
H H1A' 0.1728 0.7332 0.0620 0.153 Uiso calc PR 0.34(2) A 2
H H1B' 0.0400 0.7665 -0.0049 0.153 Uiso calc PR 0.34(2) A 2
H H1C' 0.1771 0.8926 0.0761 0.153 Uiso calc PR 0.34(2) A 2
C C2 0.2111(4) 0.7775(5) -0.0612(4) 0.0870(13) Uani d . 1 . .
H H2A 0.1692 0.7176 -0.1410 0.104 Uiso calc R 1 A 1
H H2B 0.1914 0.8713 -0.0466 0.104 Uiso calc R 1 A 1
C C3 0.287(3) 0.5362(15) -0.4207(9) 0.121(8) Uani d P 0.66(2) A 1
H H3A 0.1913 0.5461 -0.4063 0.160 Uiso calc PR 0.66(2) A 1
H H3B 0.2747 0.4448 -0.4812 0.160 Uiso calc PR 0.66(2) A 1
H H3C 0.3300 0.6126 -0.4421 0.160 Uiso calc PR 0.66(2) A 1
C C3' 0.3900(4) 0.5599(19) -0.4201(13) 0.100(8) Uani d P 0.34(2) A 2
H H3A' 0.3191 0.4835 -0.4836 0.150 Uiso calc PR 0.34(2) A 2
H H3B' 0.4887 0.5582 -0.4299 0.150 Uiso calc PR 0.34(2) A 2
H H3C' 0.3724 0.6510 -0.4156 0.150 Uiso calc PR 0.34(2) A 2
C C4 0.3732(8) 0.5430(6) -0.3294(4) 0.098(2) Uani d . 1 . .
H H4A 0.4667 0.5280 -0.3475 0.118 Uiso calc R 1 A 1
H H4B 0.3287 0.4625 -0.3116 0.118 Uiso calc R 1 A 1
C C5 0.6343(3) 0.7417(3) -0.0464(3) 0.0478(7) Uani d . 1 A .
H H5A 0.6603 0.8452 -0.0307 0.057 Uiso calc R 1 . .
C C6 0.7176(3) 0.6676(3) -0.1318(3) 0.0508(7) Uani d . 1 . .
C C7 0.7093(4) 0.5201(4) -0.1631(3) 0.0686(10) Uani d . 1 . .
H H7A 0.6543 0.4677 -0.1300 0.082 Uiso calc R 1 . .
C C8 0.7820(5) 0.4521(4) -0.2427(4) 0.0788(11) Uani d . 1 . .
H H8A 0.7770 0.3543 -0.2638 0.095 Uiso calc R 1 . .
C C9 0.8619(4) 0.5325(4) -0.2896(3) 0.0707(10) Uani d . 1 . .
C C10 0.8720(4) 0.6766(4) -0.2615(3) 0.0625(9) Uani d . 1 . .
H H10A 0.9266 0.7281 -0.2954 0.075 Uiso calc R 1 . .
C C11 0.7994(3) 0.7430(3) -0.1818(3) 0.0530(8) Uani d . 1 . .
H H11A 0.8057 0.8410 -0.1613 0.064 Uiso calc R 1 . .
C C12 0.7997(3) 0.8036(3) 0.1388(3) 0.0476(7) Uani d . 1 . .
C C13 1.0132(3) 0.9141(3) 0.2943(3) 0.0495(7) Uani d . 1 . .
C C14 1.1326(3) 0.9586(3) 0.3959(3) 0.0520(7) Uani d . 1 . .
C C15 1.2501(4) 1.0796(4) 0.4250(3) 0.0669(9) Uani d . 1 . .
H H15A 1.2531 1.1326 0.3794 0.080 Uiso calc R 1 . .
C C16 1.3619(4) 1.1212(4) 0.5212(3) 0.0740(11) Uani d . 1 . .
H H16A 1.4403 1.2015 0.5391 0.089 Uiso calc R 1 . .
C C17 1.3596(4) 1.0462(4) 0.5914(3) 0.0668(10) Uani d . 1 . .
C C18 1.2444(4) 0.9278(4) 0.5645(3) 0.0672(9) Uani d . 1 . .
H H18A 1.2419 0.8754 0.6105 0.081 Uiso calc R 1 . .
C C19 1.1308(4) 0.8862(4) 0.4678(3) 0.0598(8) Uani d . 1 . .
H H19A 1.0515 0.8072 0.4513 0.072 Uiso calc R 1 . .
C C20 1.4839(6) 1.0152(6) 0.7528(4) 0.1139(18) Uani d . 1 . .
H H20A 1.5718 1.0605 0.8136 0.171 Uiso calc R 1 . .
H H20B 1.4877 0.9196 0.7071 0.171 Uiso calc R 1 . .
H H20C 1.3977 1.0099 0.7839 0.171 Uiso calc R 1 . .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
C2 C1 H1A 109.5
C2 C1 H1B 109.5
C2 C1 H1C 109.5
C2 C1' H1A' 109.5
C2 C1' H1B' 109.5
H1A' C1' H1B' 109.5
C2 C1' H1C' 109.5
H1A' C1' H1C' 109.5
H1B' C1' H1C' 109.5
C1' C2 O1 116.8(13)
O1 C2 C1 110.7(6)
C1' C2 H2A 128.0
O1 C2 H2A 109.5
C1 C2 H2A 109.5
C1' C2 H2B 78.1
O1 C2 H2B 109.5
C1 C2 H2B 109.5
H2A C2 H2B 108.1
C4 C3 H3A 109.5
C4 C3 H3B 109.5
C4 C3 H3C 109.5
C4 C3' H3A' 109.5
C4 C3' H3B' 111.0
H3A' C3' H3B' 109.5
C4 C3' H3C' 109.5
H3A' C3' H3C' 109.5
H3B' C3' H3C' 109.5
C3' C4 O2 116.7(10)
C3 C4 O2 118.7(7)
C3' C4 H4A 67.0
C3 C4 H4A 107.6
O2 C4 H4A 107.6
C3' C4 H4B 135.0
C3 C4 H4B 107.6
O2 C4 H4B 107.6
H4A C4 H4B 107.1
N1 C5 C6 113.1(2)
N1 C5 P 107.85(19)
C6 C5 P 109.9(2)
N1 C5 H5A 108.6
C6 C5 H5A 108.6
P C5 H5A 108.6
C11 C6 C7 118.8(3)
C11 C6 C5 120.6(3)
C7 C6 C5 120.6(3)
C8 C7 C6 120.5(3)
C8 C7 H7A 119.7
C6 C7 H7A 119.7
C9 C8 C7 118.1(3)
C9 C8 H8A 120.9
C7 C8 H8A 120.9
F C9 C10 118.7(3)
F C9 C8 118.4(4)
C10 C9 C8 122.9(4)
C9 C10 C11 118.3(3)
C9 C10 H10A 120.9
C11 C10 H10A 120.9
C10 C11 C6 121.3(3)
C10 C11 H11A 119.4
C6 C11 H11A 119.4
N2 C12 N1 123.2(3)
N2 C12 S 114.8(2)
N1 C12 S 122.0(2)
N3 C13 C14 124.2(3)
N3 C13 S 113.0(2)
C14 C13 S 122.8(2)
C19 C14 C15 117.7(3)
C19 C14 C13 121.5(3)
C15 C14 C13 120.7(3)
C16 C15 C14 120.3(4)
C16 C15 H15A 119.9
C14 C15 H15A 119.9
C15 C16 C17 121.3(3)
C15 C16 H16A 119.4
C17 C16 H16A 119.4
O4 C17 C18 124.7(4)
O4 C17 C16 116.1(4)
C18 C17 C16 119.2(3)
C17 C18 C19 119.7(4)
C17 C18 H18A 120.2
C19 C18 H18A 120.2
C14 C19 C18 121.8(3)
C14 C19 H19A 119.1
C18 C19 H19A 119.1
O4 C20 H20A 109.5
O4 C20 H20B 109.5
H20A C20 H20B 109.5
O4 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C12 N1 C5 119.7(2)
C12 N1 H1 120.1
C5 N1 H1 120.1
C12 N2 N3 111.4(3)
C13 N3 N2 113.8(2)
C2 O1 P 119.1(3)
C4 O2 P 122.2(3)
C17 O4 C20 117.4(4)
O3 P O1 116.31(15)
O3 P O2 113.80(14)
O1 P O2 103.59(14)
O3 P C5 112.94(14)
O1 P C5 102.91(14)
O2 P C5 106.07(14)
C12 S C13 87.04(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.487(13)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C1' C2 1.31(3)
C1' H1A' 0.9600
C1' H1B' 0.9600
C1' H1C' 0.9600
C2 O1 1.468(4)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.299(10)
C3 H3A 0.9600
C3 H3B 0.9600
C3 H3C 0.9600
C3' C4 1.269(14)
C3' H3A' 0.9600
C3' H3B' 0.9600
C3' H3C' 0.9600
C4 O2 1.462(5)
C4 H4A 0.9700
C4 H4B 0.9700
C5 N1 1.460(4)
C5 C6 1.518(4)
C5 P 1.806(3)
C5 H5A 0.9800
C6 C11 1.375(4)
C6 C7 1.402(4)
C7 C8 1.378(5)
C7 H7A 0.9300
C8 C9 1.368(5)
C8 H8A 0.9300
C9 F 1.359(4)
C9 C10 1.369(5)
C10 C11 1.373(5)
C10 H10A 0.9300
C11 H11A 0.9300
C12 N2 1.305(4)
C12 N1 1.371(4)
C12 S 1.723(3)
C13 N3 1.299(4)
C13 C14 1.462(4)
C13 S 1.743(3)
C14 C19 1.376(5)
C14 C15 1.393(4)
C15 C16 1.378(5)
C15 H15A 0.9300
C16 C17 1.377(5)
C16 H16A 0.9300
C17 O4 1.366(4)
C17 C18 1.368(5)
C18 C19 1.392(5)
C18 H18A 0.9300
C19 H19A 0.9300
C20 O4 1.421(6)
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
N1 H1 0.8600
N2 N3 1.387(4)
O1 P 1.555(3)
O2 P 1.563(2)
O3 P 1.459(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O3 2_665 0.86 2.13 2.795(5) 133 yes
C19 H19A S . 0.93 2.73 3.142(4) 108 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
N1 C5 C6 C11 -127.1(3)
P C5 C6 C11 112.3(3)
N1 C5 C6 C7 54.6(4)
P C5 C6 C7 -66.0(3)
C11 C6 C7 C8 0.0(5)
C5 C6 C7 C8 178.4(3)
C6 C7 C8 C9 0.0(6)
C7 C8 C9 F 179.2(4)
C7 C8 C9 C10 -0.3(7)
F C9 C10 C11 -179.0(3)
C8 C9 C10 C11 0.5(6)
C9 C10 C11 C6 -0.5(5)
C7 C6 C11 C10 0.2(5)
C5 C6 C11 C10 -178.2(3)
N3 C13 C14 C19 171.1(3)
S C13 C14 C19 -8.4(4)
N3 C13 C14 C15 -6.7(5)
S C13 C14 C15 173.7(3)
C19 C14 C15 C16 1.8(5)
C13 C14 C15 C16 179.7(3)
C14 C15 C16 C17 -0.8(6)
C15 C16 C17 O4 -179.7(4)
C15 C16 C17 C18 0.3(6)
O4 C17 C18 C19 179.3(3)
C16 C17 C18 C19 -0.7(6)
C15 C14 C19 C18 -2.3(5)
C13 C14 C19 C18 179.8(3)
C17 C18 C19 C14 1.8(5)
N2 C12 N1 C5 21.0(5)
S C12 N1 C5 -161.4(2)
C6 C5 N1 C12 77.7(3)
P C5 N1 C12 -160.5(2)
N1 C12 N2 N3 177.1(3)
S C12 N2 N3 -0.7(4)
C14 C13 N3 N2 -179.0(3)
S C13 N3 N2 0.6(4)
C12 N2 N3 C13 0.1(4)
C1' C2 O1 P 126(3)
C1 C2 O1 P 91.2(8)
C3' C4 O2 P -162.0(5)
C3 C4 O2 P 148.3(14)
C18 C17 O4 C20 5.6(6)
C16 C17 O4 C20 -174.4(4)
C2 O1 P O3 -57.8(3)
C2 O1 P O2 67.8(3)
C2 O1 P C5 178.2(3)
C4 O2 P O3 -19.2(4)
C4 O2 P O1 -146.4(4)
C4 O2 P C5 105.6(4)
N1 C5 P O3 -47.2(3)
C6 C5 P O3 76.5(2)
N1 C5 P O1 79.0(2)
C6 C5 P O1 -157.3(2)
N1 C5 P O2 -172.5(2)
C6 C5 P O2 -48.8(2)
N2 C12 S C13 0.9(3)
N1 C12 S C13 -177.0(3)
N3 C13 S C12 -0.8(3)
C14 C13 S C12 178.8(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139073162
