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#$Date: 2025-08-23 01:57:28 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301878 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/65/7706518.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_7706518
loop_
_publ_author_name
'Asok, Nayanthara'
'Gaffen, Joshua R.'
'Pradhan, Ekadashi'
'Zeng, Tao'
'Baumgartner, Thomas'
_publ_section_title
;
 Structure-reactivity studies on hypervalent square-pyramidal
 dithieno[3,2-b:2',3'-d]phospholes.
;
_journal_issue                   6
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2243
_journal_page_last               2252
_journal_paper_doi               10.1039/d1dt00062d
_journal_volume                  50
_journal_year                    2021
_chemical_formula_moiety         'C20 H9 Cl4 O2 P S2'
_chemical_formula_sum            'C20 H9 Cl4 O2 P S2'
_chemical_formula_weight         518.16
_chemical_properties_physical    Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-11-13 deposited with the CCDC.	2021-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.1160(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6769(3)
_cell_length_b                   8.6815(2)
_cell_length_c                   20.2009(5)
_cell_measurement_reflns_used    9971
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.88
_cell_volume                     2027.32(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker Apex2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 QUEST ECO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0983
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            35560
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.515
_diffrn_reflns_theta_min         2.558
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.885
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_description       cube
_exptl_crystal_F_000             1040
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.804
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4659
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0458
_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/[σ²(Fo²)+(0.0140P)²+4.2553P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0928
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3784
_reflns_number_total             4659
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt00062d2.cif
_cod_data_source_block           na001_0m_a
_cod_depositor_comments
'Adding full bibliography for 7706518--7706522.cif.'
_cod_database_code               7706518
_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_max   0.917
_shelx_estimated_absorpt_t_min   0.917
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21),
 C22(H22)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.84309(6) 0.03549(9) 0.21532(3) 0.02901(17) Uani 1 1 d . . . . .
P2 P 1.11148(5) -0.05230(8) 0.09875(3) 0.01817(15) Uani 1 1 d . . . . .
Cl3 Cl 1.46217(6) 0.34168(9) -0.05898(4) 0.03162(17) Uani 1 1 d . . . . .
S4 S 0.85203(6) -0.36582(9) 0.14110(3) 0.02839(17) Uani 1 1 d . . . . .
Cl5 Cl 1.30999(6) -0.25051(8) -0.07278(3) 0.02898(17) Uani 1 1 d . . . . .
Cl6 Cl 1.47076(6) 0.01100(9) -0.11860(3) 0.03228(18) Uani 1 1 d . . . . .
Cl7 Cl 1.30266(7) 0.40836(8) 0.05156(4) 0.03423(18) Uani 1 1 d . . . . .
O1 O 1.15681(15) -0.1252(2) 0.02678(8) 0.0231(4) Uani 1 1 d . . . . .
O2 O 1.15335(15) 0.1271(2) 0.07386(9) 0.0225(4) Uani 1 1 d . . . . .
C3 C 1.3785(2) 0.0506(3) -0.06134(12) 0.0219(5) Uani 1 1 d . . . . .
C4 C 1.3071(2) -0.0661(3) -0.04226(12) 0.0213(5) Uani 1 1 d . . . . .
C5 C 0.9318(2) -0.2018(3) 0.13563(12) 0.0215(5) Uani 1 1 d . . . . .
C6 C 1.3765(2) 0.1981(3) -0.03406(12) 0.0221(6) Uani 1 1 d . . . . .
C7 C 1.2336(2) -0.0296(3) 0.00297(12) 0.0204(5) Uani 1 1 d . . . . .
C8 C 1.0109(2) 0.0487(3) 0.14627(12) 0.0206(5) Uani 1 1 d . . . . .
C9 C 1.0179(2) -0.3740(3) 0.07013(13) 0.0256(6) Uani 1 1 d . . . . .
H9 H 1.070963 -0.408929 0.041838 0.031 Uiso 1 1 calc R . . . .
C10 C 1.2766(2) 0.0102(4) 0.20850(13) 0.0273(6) Uani 1 1 d . . . . .
H10 H 1.245636 0.111587 0.206170 0.033 Uiso 1 1 calc R . . . .
C11 C 1.2329(2) -0.0991(3) 0.16160(12) 0.0209(5) Uani 1 1 d . . . . .
C12 C 1.0042(2) 0.1974(3) 0.17478(13) 0.0250(6) Uani 1 1 d . . . . .
H12 H 1.054471 0.280263 0.168122 0.030 Uiso 1 1 calc R . . . .
C13 C 0.9286(2) -0.0498(3) 0.16400(12) 0.0216(5) Uani 1 1 d . . . . .
C14 C 1.3035(2) 0.2309(3) 0.01338(13) 0.0233(6) Uani 1 1 d . . . . .
C15 C 1.2317(2) 0.1165(3) 0.03040(12) 0.0198(5) Uani 1 1 d . . . . .
C16 C 1.0180(2) -0.2227(3) 0.09668(12) 0.0210(5) Uani 1 1 d . . . . .
C17 C 1.2805(2) -0.2464(3) 0.16487(15) 0.0289(6) Uani 1 1 d . . . . .
H17 H 1.251932 -0.321825 0.132624 0.035 Uiso 1 1 calc R . . . .
C18 C 0.9173(2) 0.2066(3) 0.21272(14) 0.0277(6) Uani 1 1 d . . . . .
H18 H 0.899365 0.297482 0.235372 0.033 Uiso 1 1 calc R . . . .
C19 C 0.9333(2) -0.4632(3) 0.08978(14) 0.0283(6) Uani 1 1 d . . . . .
H19 H 0.920443 -0.567628 0.076708 0.034 Uiso 1 1 calc R . . . .
C20 C 1.3698(3) -0.2830(4) 0.21533(17) 0.0382(8) Uani 1 1 d . . . . .
H20 H 1.402340 -0.383508 0.217554 0.046 Uiso 1 1 calc R . . . .
C21 C 1.4115(3) -0.1742(4) 0.26209(16) 0.0403(8) Uani 1 1 d . . . . .
H21 H 1.472090 -0.200089 0.296774 0.048 Uiso 1 1 calc R . . . .
C22 C 1.3657(2) -0.0281(4) 0.25885(14) 0.0375(8) Uani 1 1 d . . . . .
H22 H 1.395038 0.046776 0.291135 0.045 Uiso 1 1 calc R . . . .
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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 '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
C13 S1 C18 90.88(13) . . ?
O1 P2 C8 154.58(10) . . ?
O1 P2 C11 101.80(10) . . ?
O1 P2 C16 86.45(10) . . ?
O2 P2 O1 87.29(9) . . ?
O2 P2 C8 87.13(10) . . ?
O2 P2 C11 100.41(11) . . ?
O2 P2 C16 155.71(11) . . ?
C11 P2 C8 103.60(11) . . ?
C11 P2 C16 103.85(12) . . ?
C16 P2 C8 88.52(12) . . ?
C5 S4 C19 91.06(13) . . ?
C7 O1 P2 111.64(16) . . ?
C15 O2 P2 111.77(16) . . ?
C4 C3 Cl6 119.5(2) . . ?
C6 C3 Cl6 119.7(2) . . ?
C6 C3 C4 120.8(2) . . ?
C3 C4 Cl5 122.2(2) . . ?
C7 C4 Cl5 119.9(2) . . ?
C7 C4 C3 117.9(2) . . ?
C13 C5 S4 133.67(19) . . ?
C16 C5 S4 112.0(2) . . ?
C16 C5 C13 114.3(2) . . ?
C3 C6 Cl3 120.51(19) . . ?
C3 C6 C14 120.2(2) . . ?
C14 C6 Cl3 119.3(2) . . ?
O1 C7 C4 126.8(2) . . ?
O1 C7 C15 111.7(2) . . ?
C4 C7 C15 121.5(2) . . ?
C12 C8 P2 136.0(2) . . ?
C13 C8 P2 111.2(2) . . ?
C13 C8 C12 112.3(2) . . ?
C19 C9 C16 112.3(2) . . ?
C11 C10 C22 120.1(3) . . ?
C10 C11 P2 120.1(2) . . ?
C10 C11 C17 119.3(3) . . ?
C17 C11 P2 120.5(2) . . ?
C18 C12 C8 111.8(3) . . ?
C5 C13 S1 133.5(2) . . ?
C8 C13 S1 112.3(2) . . ?
C8 C13 C5 114.1(2) . . ?
C6 C14 Cl7 122.1(2) . . ?
C15 C14 Cl7 119.5(2) . . ?
C15 C14 C6 118.5(2) . . ?
O2 C15 C7 111.8(2) . . ?
O2 C15 C14 127.1(2) . . ?
C14 C15 C7 121.1(2) . . ?
C5 C16 P2 111.2(2) . . ?
C5 C16 C9 112.2(2) . . ?
C9 C16 P2 136.3(2) . . ?
C20 C17 C11 119.9(3) . . ?
C12 C18 S1 112.6(2) . . ?
C9 C19 S4 112.4(2) . . ?
C21 C20 C17 120.2(3) . . ?
C22 C21 C20 120.3(3) . . ?
C21 C22 C10 120.2(3) . . ?
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 C13 1.707(3) . ?
S1 C18 1.725(3) . ?
P2 O1 1.7352(18) . ?
P2 O2 1.7285(19) . ?
P2 C8 1.841(3) . ?
P2 C11 1.810(3) . ?
P2 C16 1.836(3) . ?
Cl3 C6 1.717(3) . ?
S4 C5 1.714(3) . ?
S4 C19 1.723(3) . ?
Cl5 C4 1.718(3) . ?
Cl6 C3 1.723(3) . ?
Cl7 C14 1.723(3) . ?
O1 C7 1.358(3) . ?
O2 C15 1.358(3) . ?
C3 C4 1.400(4) . ?
C3 C6 1.395(4) . ?
C4 C7 1.377(3) . ?
C5 C13 1.441(4) . ?
C5 C16 1.374(3) . ?
C6 C14 1.399(4) . ?
C7 C15 1.386(4) . ?
C8 C12 1.420(4) . ?
C8 C13 1.371(4) . ?
C9 C16 1.419(4) . ?
C9 C19 1.357(4) . ?
C10 C11 1.387(4) . ?
C10 C22 1.389(4) . ?
C11 C17 1.393(4) . ?
C12 C18 1.358(4) . ?
C14 C15 1.374(4) . ?
C17 C20 1.388(4) . ?
C20 C21 1.375(5) . ?
C21 C22 1.374(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168343835
