#------------------------------------------------------------------------------
#$Date: 2025-08-21 00:01:10 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301838 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/05/4320592.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_4320592
loop_
_publ_author_name
'A. Chandrasekaran'
'Roberta O. Day'
'Robert R. Holmes'
_publ_section_title
;
 Coordination of Carbonyl and Carboxyl Oxygen Atoms with Phosphorus in the
 Presence of Hydrogen Bonding. P-O Donor Action
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              6229
_journal_page_last               6238
_journal_paper_doi               10.1021/ic010600e
_journal_volume                  40
_journal_year                    2001
_chemical_formula_sum            'C22 H15 Cl2 O6 P'
_chemical_formula_weight         477.21
_space_group_IT_number           1
_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                99.1945(10)
_cell_angle_beta                 108.7476(11)
_cell_angle_gamma                110.6167(14)
_cell_formula_units_Z            1
_cell_length_a                   7.9711(2)
_cell_length_b                   8.3909(2)
_cell_length_c                   9.5169(3)
_cell_measurement_temperature    293(2)
_cell_volume                     536.74(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Nonius KappaCCD area detector'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3383
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         4.52
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_T_max  0.8196
_exptl_absorpt_correction_T_min  0.7603
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.10(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.414
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3383
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.414
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0401
_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)+(0.0620P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1143
_reflns_number_gt                3300
_reflns_number_total             3383
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic010600e_2.cif
_cod_data_source_block           acp41b(1B)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        536.74(2)
_cod_database_code               4320592
loop_
_symmetry_equiv_pos_as_xyz
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P P 0.52598(6) 0.15927(6) 0.05015(5) 0.03437(18) Uani 1 1 d . . .
O1 O 0.6956(2) 0.1424(2) 0.22052(19) 0.0385(4) Uani 1 1 d . . .
O2 O 0.7624(3) 0.1531(3) 0.4673(2) 0.0529(5) Uani 1 1 d . . .
O3 O 0.3694(3) 0.1768(3) -0.1162(2) 0.0436(4) Uani 1 1 d . . .
O4 O 0.1423(4) 0.0204(4) -0.3593(3) 0.0722(7) Uani 1 1 d . . .
O5 O 0.6888(5) 0.1241(3) -0.1870(3) 0.0889(11) Uani 1 1 d . . .
O6 O 0.8537(5) 0.3463(4) -0.2507(3) 0.0902(10) Uani 1 1 d . . .
H6 H 0.8725 0.2717 -0.3027 0.135 Uiso 1 1 calc R . .
C1 C 0.3850(4) 0.1797(3) 0.1615(3) 0.0381(5) Uani 1 1 d . . .
C2 C 0.2128(4) 0.2010(4) 0.1126(4) 0.0510(7) Uani 1 1 d . . .
H2 H 0.1596 0.2137 0.0149 0.061 Uiso 1 1 calc R . .
C3 C 0.1220(5) 0.2027(5) 0.2166(5) 0.0632(9) Uani 1 1 d . . .
H3 H 0.0043 0.2134 0.1855 0.076 Uiso 1 1 calc R . .
C4 C 0.1999(5) 0.1894(4) 0.3605(4) 0.0568(8) Uani 1 1 d . . .
H4 H 0.1359 0.1925 0.4265 0.068 Uiso 1 1 calc R . .
C5 C 0.3734(4) 0.1712(4) 0.4113(3) 0.0496(7) Uani 1 1 d . . .
H5 H 0.4263 0.1607 0.5099 0.060 Uiso 1 1 calc R . .
C6 C 0.4664(3) 0.1691(3) 0.3109(3) 0.0370(5) Uani 1 1 d . . .
C7 C 0.6527(4) 0.1531(3) 0.3434(3) 0.0372(5) Uani 1 1 d . . .
C11 C 0.4540(4) -0.0693(4) -0.0545(3) 0.0406(5) Uani 1 1 d . . .
C12 C 0.5167(5) -0.1929(4) -0.0047(4) 0.0535(7) Uani 1 1 d . . .
H12 H 0.6136 -0.1608 0.0946 0.064 Uiso 1 1 calc R . .
C13 C 0.4327(6) -0.3648(5) -0.1051(5) 0.0686(9) Uani 1 1 d . . .
H13 H 0.4769 -0.4474 -0.0737 0.082 Uiso 1 1 calc R . .
C14 C 0.2842(6) -0.4166(5) -0.2514(5) 0.0725(10) Uani 1 1 d . . .
H14 H 0.2265 -0.5341 -0.3157 0.087 Uiso 1 1 calc R . .
C15 C 0.2221(5) -0.2947(5) -0.3015(4) 0.0669(9) Uani 1 1 d . . .
H15 H 0.1237 -0.3282 -0.4004 0.080 Uiso 1 1 calc R . .
C16 C 0.3075(4) -0.1209(4) -0.2032(3) 0.0460(6) Uani 1 1 d . . .
C17 C 0.2602(4) 0.0267(4) -0.2385(3) 0.0493(6) Uani 1 1 d . . .
C21 C 0.7235(3) 0.3744(3) 0.0801(3) 0.0388(5) Uani 1 1 d . . .
C22 C 0.7729(4) 0.5110(4) 0.2115(3) 0.0495(6) Uani 1 1 d . . .
H22 H 0.7092 0.4863 0.2773 0.059 Uiso 1 1 calc R . .
C23 C 0.9127(5) 0.6807(4) 0.2463(4) 0.0604(8) Uani 1 1 d . . .
H23 H 0.9424 0.7692 0.3348 0.073 Uiso 1 1 calc R . .
C24 C 1.0093(5) 0.7213(4) 0.1513(4) 0.0612(8) Uani 1 1 d . . .
H24 H 1.1049 0.8365 0.1755 0.073 Uiso 1 1 calc R . .
C25 C 0.9630(5) 0.5890(4) 0.0194(4) 0.0557(8) Uani 1 1 d . . .
H25 H 1.0277 0.6161 -0.0454 0.067 Uiso 1 1 calc R . .
C26 C 0.8205(4) 0.4151(4) -0.0179(3) 0.0394(5) Uani 1 1 d . . .
C27 C 0.7796(4) 0.2783(4) -0.1600(3) 0.0418(6) Uani 1 1 d . . .
C1S C 0.6542(7) -0.2054(6) -0.4431(6) 0.0835(11) Uani 1 1 d . . .
H1S1 H 0.7660 -0.1157 -0.4495 0.100 Uiso 1 1 calc R . .
H1S2 H 0.6178 -0.1463 -0.3695 0.100 Uiso 1 1 calc R . .
Cl1S Cl 0.7187(2) -0.36639(17) -0.37758(17) 0.1004(4) Uani 1 1 d . . .
Cl2S Cl 0.4573(2) -0.3039(2) -0.6266(2) 0.1235(6) Uani 1 1 d . . .
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'
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
O3 P C11 89.17(11) . . ?
O3 P C1 94.46(10) . . ?
C11 P C1 113.11(11) . . ?
O3 P O1 177.95(9) . . ?
C11 P O1 90.50(11) . . ?
C1 P O1 87.53(10) . . ?
O3 P C21 91.35(10) . . ?
C11 P C21 133.86(11) . . ?
C1 P C21 112.84(11) . . ?
O1 P C21 87.42(9) . . ?
O3 P O5 73.71(10) . . ?
C11 P O5 66.31(9) . . ?
C1 P O5 168.10(12) . . ?
O1 P O5 104.31(9) . . ?
C21 P O5 69.65(9) . . ?
C7 O1 P 115.68(16) . . ?
C17 O3 P 116.32(18) . . ?
C27 O5 P 95.92(16) . . ?
C2 C1 C6 120.3(2) . . ?
C2 C1 P 127.3(2) . . ?
C6 C1 P 112.38(19) . . ?
C1 C2 C3 117.2(3) . . ?
C4 C3 C2 122.2(3) . . ?
C3 C4 C5 121.0(3) . . ?
C4 C5 C6 118.1(3) . . ?
C5 C6 C1 121.2(3) . . ?
C5 C6 C7 126.4(2) . . ?
C1 C6 C7 112.4(2) . . ?
O2 C7 O1 121.3(2) . . ?
O2 C7 C6 126.8(2) . . ?
O1 C7 C6 111.9(2) . . ?
C12 C11 C16 119.6(3) . . ?
C12 C11 P 129.4(2) . . ?
C16 C11 P 110.9(2) . . ?
C13 C12 C11 118.8(3) . . ?
C12 C13 C14 121.4(3) . . ?
C15 C14 C13 120.0(3) . . ?
C14 C15 C16 119.3(3) . . ?
C15 C16 C11 120.9(3) . . ?
C15 C16 C17 126.4(3) . . ?
C11 C16 C17 112.7(2) . . ?
O4 C17 O3 122.7(3) . . ?
O4 C17 C16 126.6(3) . . ?
O3 C17 C16 110.7(2) . . ?
C22 C21 C26 118.1(2) . . ?
C22 C21 P 114.99(19) . . ?
C26 C21 P 126.86(18) . . ?
C23 C22 C21 121.8(3) . . ?
C22 C23 C24 120.5(3) . . ?
C23 C24 C25 119.3(3) . . ?
C24 C25 C26 121.0(3) . . ?
C25 C26 C21 119.4(2) . . ?
C25 C26 C27 118.4(2) . . ?
C21 C26 C27 122.2(2) . . ?
O5 C27 O6 123.5(2) . . ?
O5 C27 C26 123.3(2) . . ?
O6 C27 C26 113.2(2) . . ?
Cl1S C1S Cl2S 110.5(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
P O3 1.7374(18) . ?
P C11 1.802(3) . ?
P C1 1.805(2) . ?
P O1 1.8102(18) . ?
P C21 1.834(3) . ?
P O5 2.967(2) . ?
O1 C7 1.319(3) . ?
O2 C7 1.221(3) . ?
O3 C17 1.344(3) . ?
O4 C17 1.207(4) . ?
O5 C27 1.174(4) . ?
O6 C27 1.291(4) . ?
C1 C2 1.387(4) . ?
C1 C6 1.392(3) . ?
C2 C3 1.403(4) . ?
C3 C4 1.351(5) . ?
C4 C5 1.383(5) . ?
C5 C6 1.386(4) . ?
C6 C7 1.476(4) . ?
C11 C12 1.386(4) . ?
C11 C16 1.393(4) . ?
C12 C13 1.382(5) . ?
C13 C14 1.383(6) . ?
C14 C15 1.371(6) . ?
C15 C16 1.386(5) . ?
C16 C17 1.473(5) . ?
C21 C22 1.393(4) . ?
C21 C26 1.402(3) . ?
C22 C23 1.369(4) . ?
C23 C24 1.374(5) . ?
C24 C25 1.383(5) . ?
C25 C26 1.397(4) . ?
C26 C27 1.487(3) . ?
C1S Cl1S 1.741(5) . ?
C1S Cl2S 1.749(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139133964
