#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/32/05/4320595.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_4320595
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 O P'
_chemical_formula_weight         290.28
_chemical_name_systematic
;
  ?
;
_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                107.1977(11)
_cell_angle_beta                 105.9256(13)
_cell_angle_gamma                107.9488(12)
_cell_formula_units_Z            2
_cell_length_a                   8.5843(2)
_cell_length_b                   10.1422(2)
_cell_length_c                   10.6614(3)
_cell_measurement_temperature    293(2)
_cell_volume                     772.33(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4885
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         4.12
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.9661
_exptl_absorpt_correction_T_min  0.8881
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.577
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2694
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.577
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0394
_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)+(0.0500P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1208
_reflns_number_gt                2296
_reflns_number_total             2694
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic010600e_5.cif
_cod_data_source_block           aco1a(4)
_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        772.33(3)
_cod_database_code               4320595
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P P 0.48363(6) 0.85834(5) 0.14527(4) 0.05282(19) Uani 1 1 d . . .
O O 0.1837(3) 0.5913(2) -0.07078(18) 0.1024(6) Uani 1 1 d . . .
C1 C 0.2885(2) 0.8944(2) 0.15350(19) 0.0600(4) Uani 1 1 d . . .
C2 C 0.3069(3) 1.0305(2) 0.2504(2) 0.0768(6) Uani 1 1 d . . .
H2 H 0.4201 1.1032 0.3174 0.092 Uiso 1 1 calc R . .
C3 C 0.1581(4) 1.0597(4) 0.2488(3) 0.1036(9) Uani 1 1 d . . .
H3 H 0.1732 1.1519 0.3139 0.124 Uiso 1 1 calc R . .
C4 C -0.0098(4) 0.9539(5) 0.1523(4) 0.1188(12) Uani 1 1 d . . .
H4 H -0.1086 0.9739 0.1518 0.143 Uiso 1 1 calc R . .
C5 C -0.0316(3) 0.8189(4) 0.0566(3) 0.1090(10) Uani 1 1 d . . .
H5 H -0.1462 0.7469 -0.0083 0.131 Uiso 1 1 calc R . .
C6 C 0.1145(3) 0.7869(3) 0.0543(2) 0.0760(6) Uani 1 1 d . . .
C7 C 0.0776(3) 0.6403(3) -0.0538(3) 0.0977(8) Uani 1 1 d . . .
H7 H -0.0414 0.5784 -0.1161 0.117 Uiso 1 1 calc R . .
C8 C 0.4716(2) 0.71660(17) 0.22045(17) 0.0530(4) Uani 1 1 d . . .
C9 C 0.5498(3) 0.6187(2) 0.1812(2) 0.0671(5) Uani 1 1 d . . .
H9 H 0.6087 0.6294 0.1210 0.080 Uiso 1 1 calc R . .
C10 C 0.5415(3) 0.5063(2) 0.2298(2) 0.0858(7) Uani 1 1 d . . .
H10 H 0.5946 0.4418 0.2027 0.103 Uiso 1 1 calc R . .
C11 C 0.4537(3) 0.4899(2) 0.3191(2) 0.0878(7) Uani 1 1 d . . .
H11 H 0.4456 0.4127 0.3506 0.105 Uiso 1 1 calc R . .
C12 C 0.3787(3) 0.5872(2) 0.3612(2) 0.0788(6) Uani 1 1 d . . .
H12 H 0.3227 0.5779 0.4234 0.095 Uiso 1 1 calc R . .
C13 C 0.3863(3) 0.6989(2) 0.31144(19) 0.0640(5) Uani 1 1 d . . .
H13 H 0.3333 0.7634 0.3393 0.077 Uiso 1 1 calc R . .
C14 C 0.6703(2) 1.03069(18) 0.29313(17) 0.0528(4) Uani 1 1 d . . .
C15 C 0.7665(3) 1.0368(2) 0.42444(19) 0.0644(5) Uani 1 1 d . . .
H15 H 0.7281 0.9530 0.4458 0.077 Uiso 1 1 calc R . .
C16 C 0.9188(3) 1.1661(2) 0.5238(2) 0.0787(6) Uani 1 1 d . . .
H16 H 0.9821 1.1684 0.6112 0.094 Uiso 1 1 calc R . .
C17 C 0.9775(3) 1.2915(2) 0.4943(3) 0.0870(7) Uani 1 1 d . . .
H17 H 1.0806 1.3780 0.5609 0.104 Uiso 1 1 calc R . .
C18 C 0.8815(3) 1.2875(2) 0.3643(3) 0.0865(7) Uani 1 1 d . . .
H18 H 0.9189 1.3724 0.3443 0.104 Uiso 1 1 calc R . .
C19 C 0.7309(3) 1.1585(2) 0.2649(2) 0.0700(5) Uani 1 1 d . . .
H19 H 0.6685 1.1565 0.1774 0.084 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
C1 P C8 101.84(8) . . ?
C1 P C14 102.22(8) . . ?
C8 P C14 102.04(7) . . ?
C8 P O 76.06(6) . . ?
C14 P O 176.23(7) . . ?
C1 P O 75.17(8) . . ?
C7 O P 94.26(15) . . ?
C2 C1 C6 117.72(18) . . ?
C2 C1 P 121.87(15) . . ?
C6 C1 P 120.30(15) . . ?
C1 C2 C3 121.0(2) . . ?
C4 C3 C2 120.5(3) . . ?
C5 C4 C3 119.6(2) . . ?
C4 C5 C6 121.3(3) . . ?
C5 C6 C1 119.8(2) . . ?
C5 C6 C7 117.2(2) . . ?
C1 C6 C7 123.0(2) . . ?
O C7 C6 127.1(2) . . ?
C13 C8 C9 118.07(17) . . ?
C13 C8 P 124.11(13) . . ?
C9 C8 P 117.80(14) . . ?
C10 C9 C8 121.2(2) . . ?
C9 C10 C11 119.7(2) . . ?
C12 C11 C10 120.0(2) . . ?
C11 C12 C13 120.1(2) . . ?
C12 C13 C8 120.99(18) . . ?
C15 C14 C19 118.19(17) . . ?
C15 C14 P 124.35(14) . . ?
C19 C14 P 117.05(14) . . ?
C16 C15 C14 120.71(19) . . ?
C17 C16 C15 120.5(2) . . ?
C16 C17 C18 119.4(2) . . ?
C19 C18 C17 120.2(2) . . ?
C18 C19 C14 121.0(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 C1 1.8399(17) . ?
P C8 1.8317(18) . ?
P C14 1.8347(17) . ?
P O 2.8337(17) . ?
O C7 1.194(3) . ?
C1 C2 1.389(3) . ?
C1 C6 1.409(3) . ?
C2 C3 1.394(3) . ?
C3 C4 1.366(5) . ?
C4 C5 1.364(4) . ?
C5 C6 1.394(3) . ?
C6 C7 1.461(3) . ?
C8 C13 1.386(2) . ?
C8 C9 1.389(2) . ?
C9 C10 1.375(3) . ?
C10 C11 1.382(4) . ?
C11 C12 1.371(3) . ?
C12 C13 1.377(3) . ?
C14 C15 1.389(2) . ?
C14 C19 1.394(3) . ?
C15 C16 1.383(3) . ?
C16 C17 1.379(3) . ?
C17 C18 1.386(3) . ?
C18 C19 1.376(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2035266
