#------------------------------------------------------------------------------
#$Date: 2016-03-23 14:49:44 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179308 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/05/4320594.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_4320594
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 O2 P'
_chemical_formula_weight         306.28
_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
_cell_angle_alpha                95.596(3)
_cell_angle_beta                 100.257(3)
_cell_angle_gamma                100.286(3)
_cell_formula_units_Z            2
_cell_length_a                   5.6355(3)
_cell_length_b                   11.1435(6)
_cell_length_c                   13.2057(7)
_cell_measurement_temperature    293(2)
_cell_volume                     795.75(7)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       '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  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4821
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         4.35
_exptl_absorpt_coefficient_mu    0.177
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.468
_refine_ls_goodness_of_fit_obs   1.523
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2813
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.469
_refine_ls_restrained_S_obs      1.523
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_obs          0.0399
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0430P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1142
_refine_ls_wR_factor_obs         0.1049
_reflns_number_observed          2253
_reflns_number_total             2814
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic010600e_4.cif
_cod_data_source_block           aco3(3)
_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 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0430P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0430P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4320594
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
P P 0.04827(8) 0.81816(5) 0.19704(4) 0.0490(2) Uani 1 d . .
O1 O 0.2953(3) 0.91878(13) 0.39943(11) 0.0656(4) Uani 1 d . .
O2 O 0.3162(3) 1.11049(15) 0.46931(12) 0.0788(5) Uani 1 d . .
H1 H 0.4453(55) 1.0933(27) 0.5160(24) 0.108(10) Uiso 1 d . .
C1 C -0.0987(3) 0.9473(2) 0.23335(14) 0.0486(4) Uani 1 d . .
C2 C -0.2982(4) 0.9734(2) 0.1667(2) 0.0602(5) Uani 1 d . .
H2 H -0.3607(4) 0.9231(2) 0.1037(2) 0.072 Uiso 1 calc R .
C3 C -0.4070(4) 1.0716(2) 0.1911(2) 0.0690(6) Uani 1 d . .
H3 H -0.5409(4) 1.0860(2) 0.1449(2) 0.083 Uiso 1 calc R .
C4 C -0.3168(4) 1.1480(2) 0.2835(2) 0.0706(6) Uani 1 d . .
H4 H -0.3921(4) 1.2128(2) 0.3008(2) 0.085 Uiso 1 calc R .
C5 C -0.1151(4) 1.1280(2) 0.3500(2) 0.0618(5) Uani 1 d . .
H5 H -0.0520(4) 1.1809(2) 0.4116(2) 0.074 Uiso 1 calc R .
C6 C -0.0032(4) 1.0294(2) 0.32647(14) 0.0518(5) Uani 1 d . .
C7 C 0.2131(4) 1.0131(2) 0.40110(14) 0.0552(5) Uani 1 d . .
C8 C -0.0723(3) 0.7003(2) 0.27252(13) 0.0472(4) Uani 1 d . .
C9 C -0.2544(4) 0.7080(2) 0.3295(2) 0.0639(5) Uani 1 d . .
H9 H -0.3304(4) 0.7756(2) 0.3285(2) 0.077 Uiso 1 calc R .
C10 C -0.3244(5) 0.6159(2) 0.3880(2) 0.0748(7) Uani 1 d . .
H10 H -0.4448(5) 0.6228(2) 0.4269(2) 0.090 Uiso 1 calc R .
C11 C -0.2169(5) 0.5148(2) 0.3887(2) 0.0759(7) Uani 1 d . .
H11 H -0.2636(5) 0.4535(2) 0.4284(2) 0.091 Uiso 1 calc R .
C12 C -0.0410(5) 0.5043(2) 0.3312(2) 0.0800(7) Uani 1 d . .
H12 H 0.0300(5) 0.4351(2) 0.3304(2) 0.096 Uiso 1 calc R .
C13 C 0.0304(4) 0.5965(2) 0.2743(2) 0.0661(6) Uani 1 d . .
H13 H 0.1513(4) 0.5888(2) 0.2359(2) 0.079 Uiso 1 calc R .
C14 C -0.1330(3) 0.7553(2) 0.06695(14) 0.0493(4) Uani 1 d . .
C15 C -0.3701(4) 0.6844(2) 0.0452(2) 0.0653(6) Uani 1 d . .
H15 H -0.4539(4) 0.6708(2) 0.0990(2) 0.078 Uiso 1 calc R .
C16 C -0.4825(5) 0.6340(2) -0.0553(2) 0.0757(7) Uani 1 d . .
H16 H -0.6413(5) 0.5870(2) -0.0689(2) 0.091 Uiso 1 calc R .
C17 C -0.3599(5) 0.6532(2) -0.1352(2) 0.0806(7) Uani 1 d . .
H17 H -0.4335(5) 0.6169(2) -0.2025(2) 0.097 Uiso 1 calc R .
C18 C -0.1304(5) 0.7255(3) -0.1158(2) 0.0931(9) Uani 1 d . .
H18 H -0.0498(5) 0.7410(3) -0.1702(2) 0.112 Uiso 1 calc R .
C19 C -0.0178(4) 0.7755(2) -0.0155(2) 0.0717(6) Uani 1 d . .
H19 H 0.1395(4) 0.8240(2) -0.0030(2) 0.086 Uiso 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
C8 P C1 102.66(8) . . ?
C14 P C1 102.22(9) . . ?
C1 P O1 74.36(7) . . ?
C8 P C14 100.31(8) . . ?
C8 P O1 78.59(6) . . ?
C14 P O1 175.97(7) . . ?
C7 O1 H1 122.0(10) . 2_676 ?
C7 O1 P 96.08(12) . . ?
H1 O1 P 137.8(9) 2_676 . ?
C2 C1 C6 116.9(2) . . ?
C2 C1 P 121.26(14) . . ?
C6 C1 P 121.73(15) . . ?
C3 C2 C1 122.3(2) . . ?
C4 C3 C2 120.0(2) . . ?
C5 C4 C3 119.6(2) . . ?
C4 C5 C6 121.0(2) . . ?
C5 C6 C1 120.1(2) . . ?
C5 C6 C7 118.3(2) . . ?
C1 C6 C7 121.5(2) . . ?
O1 C7 O2 122.0(2) . . ?
O1 C7 C6 123.7(2) . . ?
O2 C7 C6 114.3(2) . . ?
C13 C8 C9 117.5(2) . . ?
C13 C8 P 117.27(15) . . ?
C9 C8 P 125.2(2) . . ?
C8 C9 C10 120.6(2) . . ?
C11 C10 C9 120.3(2) . . ?
C12 C11 C10 120.0(2) . . ?
C11 C12 C13 119.6(2) . . ?
C12 C13 C8 122.0(2) . . ?
C19 C14 C15 117.7(2) . . ?
C19 C14 P 116.65(15) . . ?
C15 C14 P 125.60(15) . . ?
C16 C15 C14 120.7(2) . . ?
C17 C16 C15 120.1(2) . . ?
C18 C17 C16 120.0(2) . . ?
C17 C18 C19 119.9(2) . . ?
C18 C19 C14 121.6(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 1.849(2) . ?
P C8 1.833(2) . ?
P C14 1.836(2) . ?
P O1 2.8057(14) . ?
O1 C7 1.222(2) . ?
O1 H1 1.71(3) 2_676 ?
O2 C7 1.313(2) . ?
C1 C2 1.392(3) . ?
C1 C6 1.417(3) . ?
C2 C3 1.385(3) . ?
C3 C4 1.376(3) . ?
C4 C5 1.373(3) . ?
C5 C6 1.397(3) . ?
C6 C7 1.475(3) . ?
C8 C13 1.383(3) . ?
C8 C9 1.386(3) . ?
C9 C10 1.388(3) . ?
C10 C11 1.371(4) . ?
C11 C12 1.366(3) . ?
C12 C13 1.375(3) . ?
C14 C19 1.379(3) . ?
C14 C15 1.391(3) . ?
C15 C16 1.381(3) . ?
C16 C17 1.373(4) . ?
C17 C18 1.362(4) . ?
C18 C19 1.378(3) . ?
