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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/7/70/65/7706520.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_7706520
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         'C14 H9 O P S2, C6 H2 Cl4 O2'
_chemical_formula_sum            'C20 H11 Cl4 O3 P S2'
_chemical_formula_weight         536.18
_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
_atom_sites_solution_primary     difmap
_audit_creation_date             2020-09-10
_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                116.199(3)
_cell_angle_beta                 104.509(3)
_cell_angle_gamma                91.081(3)
_cell_formula_units_Z            2
_cell_length_a                   7.4476(7)
_cell_length_b                   12.5959(13)
_cell_length_c                   13.2064(13)
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.54
_cell_measurement_theta_min      2.86
_cell_volume                     1064.13(19)
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0720
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            46942
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         30.568
_diffrn_reflns_theta_min         2.857
_exptl_absorpt_coefficient_mu    0.850
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_description       Hexagonal
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         6527
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0306
_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)+(0.0321P)²+0.5391P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0831
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5723
_reflns_number_total             6527
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt00062d2.cif
_cod_data_source_block           na_p3_27a_0m_a
_cod_depositor_comments
'Adding full bibliography for 7706518--7706522.cif.'
_cod_original_cell_volume        1064.13(18)
_cod_database_code               7706520
_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   0.959
_shelx_estimated_absorpt_t_min   0.816
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00J(H00J), C00M(H00M), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00T(H00T), C00U(H00U)
2.b Idealised tetrahedral OH refined as rotating group:
 O009(H009), O00A(H00A)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
P001 P 0.40067(5) 0.61284(3) 0.77717(3) 0.02140(7) Uani 1 1 d . . . . .
Cl02 Cl 0.16553(6) 0.22060(4) 0.16956(3) 0.03819(9) Uani 1 1 d . . . . .
S003 S 0.42022(6) 0.64529(4) 1.10958(3) 0.03348(9) Uani 1 1 d . . . . .
Cl04 Cl 0.16671(7) -0.12713(3) 0.30454(4) 0.04284(10) Uani 1 1 d . . . . .
Cl05 Cl 0.12401(6) -0.05284(4) 0.10325(3) 0.04304(10) Uani 1 1 d . . . . .
Cl06 Cl 0.31780(7) 0.07044(3) 0.56804(3) 0.04189(10) Uani 1 1 d . . . . .
S007 S -0.02951(6) 0.47639(4) 0.85849(4) 0.04162(10) Uani 1 1 d . . . . .
O008 O 0.50987(14) 0.54296(8) 0.69454(8) 0.02652(19) Uani 1 1 d . . . . .
O009 O 0.32163(16) 0.38146(9) 0.42934(9) 0.0310(2) Uani 1 1 d . . . . .
H009 H 0.357401 0.392527 0.378811 0.047 Uiso 1 1 calc GR . . . .
O00A O 0.39660(17) 0.30865(9) 0.59859(8) 0.0323(2) Uani 1 1 d . . . . .
H00A H 0.416373 0.377158 0.604155 0.048 Uiso 1 1 calc GR . . . .
C00B C 0.32442(18) 0.22843(11) 0.48433(11) 0.0237(2) Uani 1 1 d . . . . .
C00C C 0.34453(18) 0.74462(11) 0.76392(11) 0.0241(2) Uani 1 1 d . . . . .
C00D C 0.48725(18) 0.65187(11) 0.93084(11) 0.0233(2) Uani 1 1 d . . . . .
C00E C 0.28882(18) 0.26262(11) 0.39428(11) 0.0239(2) Uani 1 1 d . . . . .
C00F C 0.34833(19) 0.61206(12) 0.96430(12) 0.0256(2) Uani 1 1 d . . . . .
C00G C 0.18470(18) 0.53267(12) 0.76045(12) 0.0257(2) Uani 1 1 d . . . . .
C00H C 0.6542(2) 0.70895(12) 1.02519(12) 0.0269(2) Uani 1 1 d . . . . .
H00H H 0.764278 0.741351 1.018412 0.032 Uiso 1 1 calc R . . . .
C00I C 0.2839(2) 0.10837(12) 0.45527(12) 0.0264(2) Uani 1 1 d . . . . .
C00J C 0.6374(2) 0.71161(13) 1.12714(12) 0.0314(3) Uani 1 1 d . . . . .
H00J H 0.734848 0.746223 1.199505 0.038 Uiso 1 1 calc R . . . .
C00K C 0.2197(2) 0.02065(11) 0.33795(12) 0.0275(3) Uani 1 1 d . . . . .
C00L C 0.19316(19) 0.05399(12) 0.24866(11) 0.0278(3) Uani 1 1 d . . . . .
C00M C 0.3470(2) 0.85210(13) 0.86144(13) 0.0324(3) Uani 1 1 d . . . . .
H00M H 0.381860 0.857756 0.938149 0.039 Uiso 1 1 calc R . . . .
C00N C 0.17793(19) 0.54624(12) 0.86860(13) 0.0268(2) Uani 1 1 d . . . . .
C00O C 0.22059(19) 0.17488(12) 0.27758(11) 0.0262(2) Uani 1 1 d . . . . .
C00P C 0.2915(2) 0.73636(14) 0.65090(13) 0.0319(3) Uani 1 1 d . . . . .
H00P H 0.289398 0.663139 0.584164 0.038 Uiso 1 1 calc R . . . .
C00Q C 0.0207(2) 0.46407(14) 0.66822(14) 0.0341(3) Uani 1 1 d . . . . .
H00Q H 0.001654 0.446089 0.588123 0.041 Uiso 1 1 calc R . . . .
C00R C 0.2981(3) 0.95114(14) 0.84597(16) 0.0400(3) Uani 1 1 d . . . . .
H00R H 0.300577 1.024847 0.912265 0.048 Uiso 1 1 calc R . . . .
C00S C 0.2462(2) 0.94230(15) 0.73443(17) 0.0402(4) Uani 1 1 d . . . . .
H00S H 0.212826 1.010282 0.724538 0.048 Uiso 1 1 calc R . . . .
C00T C -0.1063(2) 0.42711(16) 0.70880(17) 0.0407(4) Uani 1 1 d . . . . .
H00T H -0.224245 0.379431 0.659841 0.049 Uiso 1 1 calc R . . . .
C00U C 0.2419(2) 0.83619(16) 0.63696(16) 0.0403(4) Uani 1 1 d . . . . .
H00U H 0.205139 0.831225 0.560543 0.048 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'
Cl Cl 0.1484 0.1585 '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'
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
O008 P001 C00C 111.61(6) . . ?
O008 P001 C00D 119.61(6) . . ?
O008 P001 C00G 115.44(6) . . ?
C00C P001 C00D 108.74(6) . . ?
C00C P001 C00G 106.87(6) . . ?
C00G P001 C00D 92.64(6) . . ?
C00F S003 C00J 91.57(7) . . ?
C00N S007 C00T 91.52(7) . . ?
O00A C00B C00E 121.86(11) . . ?
O00A C00B C00I 118.82(11) . . ?
C00I C00B C00E 119.32(12) . . ?
C00M C00C P001 121.98(10) . . ?
C00M C00C C00P 119.99(13) . . ?
C00P C00C P001 118.00(10) . . ?
C00F C00D P001 108.90(10) . . ?
C00F C00D C00H 112.40(12) . . ?
C00H C00D P001 138.69(10) . . ?
O009 C00E C00B 116.12(11) . . ?
O009 C00E C00O 124.79(12) . . ?
C00O C00E C00B 119.08(12) . . ?
C00D C00F S003 111.80(10) . . ?
C00D C00F C00N 114.45(12) . . ?
C00N C00F S003 133.65(10) . . ?
C00N C00G P001 109.49(10) . . ?
C00N C00G C00Q 113.08(13) . . ?
C00Q C00G P001 137.40(12) . . ?
C00J C00H C00D 111.77(13) . . ?
C00B C00I Cl06 118.17(10) . . ?
C00B C00I C00K 121.15(12) . . ?
C00K C00I Cl06 120.67(10) . . ?
C00H C00J S003 112.46(11) . . ?
C00I C00K Cl04 120.16(11) . . ?
C00L C00K Cl04 120.41(10) . . ?
C00L C00K C00I 119.40(12) . . ?
C00K C00L Cl05 120.38(11) . . ?
C00K C00L C00O 119.53(12) . . ?
C00O C00L Cl05 120.09(11) . . ?
C00R C00M C00C 119.67(14) . . ?
C00F C00N S007 134.36(11) . . ?
C00G C00N S007 111.38(11) . . ?
C00G C00N C00F 114.22(12) . . ?
C00E C00O Cl02 117.89(10) . . ?
C00E C00O C00L 121.26(12) . . ?
C00L C00O Cl02 120.83(10) . . ?
C00U C00P C00C 119.57(14) . . ?
C00T C00Q C00G 111.53(15) . . ?
C00S C00R C00M 119.99(15) . . ?
C00R C00S C00U 120.97(14) . . ?
C00Q C00T S007 112.49(12) . . ?
C00S C00U C00P 119.81(15) . . ?
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
P001 O008 1.5002(10) . ?
P001 C00C 1.7907(13) . ?
P001 C00D 1.7964(13) . ?
P001 C00G 1.7943(13) . ?
Cl02 C00O 1.7251(14) . ?
S003 C00F 1.7062(14) . ?
S003 C00J 1.7200(16) . ?
Cl04 C00K 1.7250(14) . ?
Cl05 C00L 1.7206(13) . ?
Cl06 C00I 1.7187(14) . ?
S007 C00N 1.7089(14) . ?
S007 C00T 1.720(2) . ?
O009 C00E 1.3536(16) . ?
O00A C00B 1.3468(15) . ?
C00B C00E 1.4030(18) . ?
C00B C00I 1.3921(18) . ?
C00C C00M 1.3926(19) . ?
C00C C00P 1.4002(19) . ?
C00D C00F 1.3865(18) . ?
C00D C00H 1.4195(18) . ?
C00E C00O 1.3919(18) . ?
C00F C00N 1.4583(19) . ?
C00G C00N 1.3758(19) . ?
C00G C00Q 1.4170(19) . ?
C00H C00J 1.3692(19) . ?
C00I C00K 1.3954(18) . ?
C00K C00L 1.389(2) . ?
C00L C00O 1.3935(19) . ?
C00M C00R 1.391(2) . ?
C00P C00U 1.393(2) . ?
C00Q C00T 1.363(2) . ?
C00R C00S 1.378(3) . ?
C00S C00U 1.379(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168343837
