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#$Date: 2025-08-21 00:01:10 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301838 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/05/4320593.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_4320593
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            'C19 H15 O3 P'
_chemical_formula_weight         322.28
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 131.4570(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.1056(6)
_cell_length_b                   8.5047(3)
_cell_length_c                   19.1412(6)
_cell_measurement_temperature    293(2)
_cell_volume                     3184.98(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5252
_diffrn_reflns_theta_full        25.11
_diffrn_reflns_theta_max         25.11
_diffrn_reflns_theta_min         4.28
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  0.9908
_exptl_absorpt_correction_T_min  0.8739
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.503
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2800
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.503
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0610P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1400
_reflns_number_gt                2213
_reflns_number_total             2800
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic010600e_3.cif
_cod_data_source_block           aco2(2)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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        3184.97(16)
_cod_database_code               4320593
loop_
_symmetry_equiv_pos_as_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'
'-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P P 0.10552(3) 0.22214(7) 0.98107(4) 0.0578(2) Uani 1 1 d . . .
O1 O 0.13851(8) 0.3321(2) 0.96070(11) 0.0719(5) Uani 1 1 d . . .
O2 O 0.24963(8) 0.1025(3) 1.07535(11) 0.0877(6) Uani 1 1 d . . .
O3 O 0.24410(9) 0.0267(2) 0.96022(13) 0.0831(6) Uani 1 1 d . . .
H1 H 0.2860(18) 0.090(4) 0.992(2) 0.125 Uiso 1 1 d . . .
C1 C 0.10083(10) 0.0220(3) 0.94438(14) 0.0606(6) Uani 1 1 d . . .
C2 C 0.04228(13) -0.0685(4) 0.90421(18) 0.0824(8) Uani 1 1 d . . .
H2 H 0.0063 -0.0250 0.8969 0.099 Uiso 1 1 calc R . .
C3 C 0.03692(17) -0.2210(4) 0.8753(2) 0.0979(10) Uani 1 1 d . . .
H3 H -0.0019 -0.2801 0.8501 0.118 Uiso 1 1 calc R . .
C4 C 0.08912(17) -0.2854(4) 0.8838(2) 0.0922(9) Uani 1 1 d . . .
H4 H 0.0858 -0.3884 0.8649 0.111 Uiso 1 1 calc R . .
C5 C 0.14638(13) -0.1973(3) 0.92049(18) 0.0747(7) Uani 1 1 d . . .
H5 H 0.1807 -0.2401 0.9237 0.090 Uiso 1 1 calc R . .
C6 C 0.15356(10) -0.0455(3) 0.95274(13) 0.0595(6) Uani 1 1 d . . .
C7 C 0.22044(10) 0.0376(3) 1.00260(14) 0.0580(5) Uani 1 1 d . . .
C8 C 0.01726(11) 0.2773(3) 0.91635(16) 0.0656(6) Uani 1 1 d . . .
C9 C -0.01124(12) 0.3038(3) 0.95387(18) 0.0712(6) Uani 1 1 d . . .
H9 H 0.0153 0.2959 1.0180 0.085 Uiso 1 1 calc R . .
C10 C -0.07992(13) 0.3427(4) 0.8973(2) 0.0898(9) Uani 1 1 d . . .
H10 H -0.0993 0.3588 0.9235 0.108 Uiso 1 1 calc R . .
C11 C -0.11910(13) 0.3575(3) 0.8032(2) 0.0838(8) Uani 1 1 d . . .
H11 H -0.1648 0.3860 0.7655 0.101 Uiso 1 1 calc R . .
C12 C -0.09136(16) 0.3307(6) 0.7652(2) 0.1281(15) Uani 1 1 d . . .
H12 H -0.1181 0.3378 0.7011 0.154 Uiso 1 1 calc R . .
C13 C -0.02372(16) 0.2931(7) 0.8214(2) 0.152(2) Uani 1 1 d . . .
H13 H -0.0047 0.2776 0.7945 0.182 Uiso 1 1 calc R . .
C14 C 0.14637(10) 0.2139(2) 1.10214(14) 0.0527(5) Uani 1 1 d . . .
C15 C 0.19747(12) 0.3204(3) 1.16349(16) 0.0676(6) Uani 1 1 d . . .
H15 H 0.2106 0.3943 1.1422 0.081 Uiso 1 1 calc R . .
C16 C 0.22933(13) 0.3172(3) 1.25738(17) 0.0762(7) Uani 1 1 d . . .
H16 H 0.2637 0.3892 1.2987 0.091 Uiso 1 1 calc R . .
C17 C 0.21031(14) 0.2092(3) 1.28866(17) 0.0751(7) Uani 1 1 d . . .
H17 H 0.2318 0.2077 1.3514 0.090 Uiso 1 1 calc R . .
C18 C 0.15974(14) 0.1024(3) 1.22868(17) 0.0767(7) Uani 1 1 d . . .
H18 H 0.1471 0.0288 1.2508 0.092 Uiso 1 1 calc R . .
C19 C 0.12746(12) 0.1042(3) 1.13520(15) 0.0644(6) Uani 1 1 d . . .
H19 H 0.0931 0.0319 1.0945 0.077 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'
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
O1 P C1 113.02(10) . . ?
O1 P C8 110.65(10) . . ?
O1 P C14 114.18(10) . . ?
C1 P C8 104.40(11) . . ?
C1 P C14 107.01(10) . . ?
C8 P C14 106.95(10) . . ?
O1 P O2 70.51(8) . . ?
C1 P O2 70.10(8) . . ?
C8 P O2 174.07(10) . . ?
C14 P O2 77.28(7) . . ?
C7 O2 P 83.11(13) . . ?
C6 C1 C2 118.1(2) . . ?
C6 C1 P 122.08(16) . . ?
C2 C1 P 119.83(19) . . ?
C3 C2 C1 121.3(3) . . ?
C4 C3 C2 119.8(3) . . ?
C3 C4 C5 120.0(3) . . ?
C4 C5 C6 120.9(3) . . ?
C5 C6 C1 119.8(2) . . ?
C5 C6 C7 118.6(2) . . ?
C1 C6 C7 121.5(2) . . ?
O2 C7 O3 123.9(2) . . ?
O2 C7 C6 122.4(2) . . ?
O3 C7 C6 113.61(19) . . ?
C9 C8 C13 117.8(2) . . ?
C9 C8 P 125.30(18) . . ?
C13 C8 P 116.9(2) . . ?
C8 C9 C10 120.4(2) . . ?
C11 C10 C9 120.2(3) . . ?
C12 C11 C10 119.8(2) . . ?
C11 C12 C13 119.6(3) . . ?
C12 C13 C8 122.1(3) . . ?
C15 C14 C19 119.2(2) . . ?
C15 C14 P 119.01(17) . . ?
C19 C14 P 121.78(16) . . ?
C14 C15 C16 120.0(2) . . ?
C17 C16 C15 120.1(2) . . ?
C16 C17 C18 120.6(2) . . ?
C17 C18 C19 120.0(2) . . ?
C18 C19 C14 120.1(2) . . ?
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 O1 1.4878(16) . ?
P C1 1.814(3) . ?
P C8 1.812(2) . ?
P C14 1.800(2) . ?
P O2 3.0750(19) . ?
O2 C7 1.191(3) . ?
O3 C7 1.308(3) . ?
C1 C2 1.401(3) . ?
C1 C6 1.399(3) . ?
C2 C3 1.381(4) . ?
C3 C4 1.374(5) . ?
C4 C5 1.378(4) . ?
C5 C6 1.390(4) . ?
C6 C7 1.501(3) . ?
C8 C9 1.352(3) . ?
C8 C13 1.376(4) . ?
C9 C10 1.388(3) . ?
C10 C11 1.367(4) . ?
C11 C12 1.341(4) . ?
C12 C13 1.365(4) . ?
C14 C15 1.380(3) . ?
C14 C19 1.388(3) . ?
C15 C16 1.394(3) . ?
C16 C17 1.357(4) . ?
C17 C18 1.371(4) . ?
C18 C19 1.384(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4247056
2 PubChem 5070268
