#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/63/2206341.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2206341
loop_
_publ_author_name
'Yulya V. Nelubina'
'Diana V. Alexanyan'
'Vladimir A. Kozlov'
'Konstantin A. Lyssenko'
'Irina L. Odinets'
_publ_section_title
;
 A monoclinic polymorph of α-diphenylphosphoryl-o-cresol
;
_journal_coeditor_code           BH6014
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2539
_journal_page_last               o2541
_journal_paper_doi               10.1107/S1600536805021811
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C19 H17 O2 P'
_chemical_formula_moiety         'C19 H17 O2 P'
_chemical_formula_sum            'C19 H17 O2 P'
_chemical_formula_weight         308.30
_chemical_melting_point          429.0
_chemical_name_common            α-Diphenylphosphoryl-o-cresol
_chemical_name_systematic        2-[(diphenylphosphoryl)methyl]phenol
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.43(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.092(2)
_cell_length_b                   10.521(2)
_cell_length_c                   14.699(3)
_cell_measurement_reflns_used    48
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      12.20
_cell_measurement_theta_min      4.20
_cell_volume                     1560.7(5)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'PROFIT (Strel'tsov & Zavodnik, 1989)'
_computing_molecular_graphics    SHELXTL-Plus
_computing_publication_material  SHELXTL-Plus
_computing_structure_refinement  SHELXTL-Plus
_computing_structure_solution    'SHELXTL-Plus (Sheldrick, 1994)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4817
_diffrn_reflns_theta_full        29.96
_diffrn_reflns_theta_max         29.96
_diffrn_reflns_theta_min         2.38
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 98
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.269
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4519
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0403
_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)+(0.0705P)²+0.2609P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1194
_reflns_number_gt                3352
_reflns_number_total             4519
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh6014.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2206341
_cod_database_fobs_code          2206341
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_type_symbol
P1 0.54374(3) 0.26801(3) 0.14859(2) 0.03072(11) Uani d 1 P
O1 0.43072(10) 0.32461(11) 0.09655(7) 0.0385(2) Uani d 1 O
O2 0.63300(11) 0.54052(11) 0.04973(7) 0.0405(2) Uani d 1 O
H2O 0.612(2) 0.587(2) 0.0082(17) 0.074(7) Uiso d 1 H
C1 0.65700(14) 0.38394(15) 0.19982(11) 0.0379(3) Uani d 1 C
H2 0.7326(18) 0.3865(18) 0.1627(12) 0.045(5) Uiso d 1 H
H1A 0.679(2) 0.351(2) 0.2596(14) 0.056(5) Uiso d 1 H
C2 0.59881(13) 0.51492(14) 0.20688(9) 0.0330(3) Uani d 1 C
C3 0.58598(13) 0.58942(13) 0.12852(9) 0.0325(3) Uani d 1 C
C4 0.53058(16) 0.71019(15) 0.13393(11) 0.0398(3) Uani d 1 C
H4 0.5192(17) 0.7589(17) 0.0772(12) 0.038(4) Uiso d 1 H
C5 0.49068(18) 0.75807(16) 0.21731(12) 0.0461(4) Uani d 1 C
H5 0.4537(19) 0.843(2) 0.2205(13) 0.051(5) Uiso d 1 H
C14 0.48213(13) 0.16999(13) 0.23957(9) 0.0313(3) Uani d 1 C
C6 0.50678(17) 0.68697(18) 0.29543(12) 0.0464(4) Uani d 1 C
H6 0.483(2) 0.719(2) 0.3561(14) 0.056(6) Uiso d 1 H
C19 0.56449(15) 0.12126(16) 0.30764(10) 0.0393(3) Uani d 1 C
H19 0.6536(18) 0.1403(18) 0.3072(11) 0.042(5) Uiso d 1 H
C7 0.55956(15) 0.56553(17) 0.28973(10) 0.0403(3) Uani d 1 C
H7 0.5688(18) 0.5105(18) 0.3445(13) 0.043(5) Uiso d 1 H
C8 0.64706(14) 0.16822(15) 0.07898(9) 0.0353(3) Uani d 1 C
C16 0.29732(17) 0.05968(17) 0.30573(12) 0.0449(4) Uani d 1 C
H16 0.208(2) 0.042(2) 0.3074(14) 0.057(6) Uiso d 1 H
C15 0.34838(14) 0.13939(16) 0.23964(10) 0.0381(3) Uani d 1 C
H15 0.2941(19) 0.1708(19) 0.1949(13) 0.048(5) Uiso d 1 H
C18 0.51217(18) 0.04203(18) 0.37391(11) 0.0465(4) Uani d 1 C
H18 0.572(2) 0.011(2) 0.4166(15) 0.072(7) Uiso d 1 H
C9 0.73272(18) 0.22591(19) 0.01746(12) 0.0489(4) Uani d 1 C
H9 0.736(2) 0.325(3) 0.0153(15) 0.068(6) Uiso d 1 H
C17 0.37949(18) 0.01132(17) 0.37272(11) 0.0459(4) Uani d 1 C
H17 0.343(2) -0.043(2) 0.4181(14) 0.053(5) Uiso d 1 H
C13 0.63801(18) 0.03653(17) 0.08029(12) 0.0478(4) Uani d 1 C
H13 0.576(2) -0.005(2) 0.1227(14) 0.053(5) Uiso d 1 H
C10 0.8080(2) 0.1529(2) -0.04071(13) 0.0584(5) Uani d 1 C
H10 0.868(2) 0.190(3) -0.0853(17) 0.083(8) Uiso d 1 H
C12 0.7131(2) -0.0360(2) 0.02158(16) 0.0635(5) Uani d 1 C
H12 0.710(2) -0.133(2) 0.0254(16) 0.079(7) Uiso d 1 H
C11 0.7978(2) 0.0225(2) -0.03846(14) 0.0601(5) Uani d 1 C
H11 0.845(3) -0.020(3) -0.0789(18) 0.082(8) Uiso d 1 H
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_publ_flag
O1 P1 C14 109.99(6) yes
O1 P1 C8 112.60(7) yes
C14 P1 C8 106.97(7) ?
O1 P1 C1 114.68(7) yes
C14 P1 C1 107.09(7) ?
C8 P1 C1 105.04(7) ?
C3 O2 H2O 108.6(17) ?
C2 C1 P1 113.37(10) ?
C2 C1 H2 109.4(12) ?
P1 C1 H2 106.7(11) ?
C2 C1 H1A 110.5(13) ?
P1 C1 H1A 105.9(13) ?
H2 C1 H1A 110.9(17) ?
C7 C2 C3 118.81(14) ?
C7 C2 C1 121.77(14) ?
C3 C2 C1 119.41(13) ?
O2 C3 C4 122.60(13) ?
O2 C3 C2 117.38(13) ?
C4 C3 C2 119.99(13) ?
C5 C4 C3 120.11(15) ?
C5 C4 H4 121.7(11) ?
C3 C4 H4 118.1(11) ?
C6 C5 C4 120.36(16) ?
C6 C5 H5 120.2(11) ?
C4 C5 H5 119.4(11) ?
C15 C14 C19 119.27(13) ?
C15 C14 P1 118.30(11) ?
C19 C14 P1 122.40(11) ?
C5 C6 C7 119.49(15) ?
C5 C6 H6 122.8(13) ?
C7 C6 H6 117.7(13) ?
C18 C19 C14 119.76(14) ?
C18 C19 H19 120.8(11) ?
C14 C19 H19 119.5(11) ?
C6 C7 C2 121.20(15) ?
C6 C7 H7 121.4(11) ?
C2 C7 H7 117.4(11) ?
C13 C8 C9 118.97(15) ?
C13 C8 P1 122.32(11) ?
C9 C8 P1 118.57(13) ?
C17 C16 C15 119.92(15) ?
C17 C16 H16 119.3(13) ?
C15 C16 H16 120.7(13) ?
C16 C15 C14 120.52(14) ?
C16 C15 H15 119.9(12) ?
C14 C15 H15 119.6(12) ?
C17 C18 C19 120.42(15) ?
C17 C18 H18 123.6(14) ?
C19 C18 H18 116.0(14) ?
C10 C9 C8 120.38(18) ?
C10 C9 H9 121.3(12) ?
C8 C9 H9 118.3(12) ?
C18 C17 C16 120.11(15) ?
C18 C17 H17 120.8(12) ?
C16 C17 H17 119.1(12) ?
C12 C13 C8 120.36(17) ?
C12 C13 H13 119.9(13) ?
C8 C13 H13 119.7(12) ?
C11 C10 C9 119.86(18) ?
C11 C10 H10 117.5(16) ?
C9 C10 H10 122.6(16) ?
C11 C12 C13 119.94(19) ?
C11 C12 H12 120.0(14) ?
C13 C12 H12 119.9(14) ?
C10 C11 C12 120.48(18) ?
C10 C11 H11 116.5(17) ?
C12 C11 H11 123.0(17) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O1 1.4925(11) yes
P1 C14 1.8031(14) yes
P1 C8 1.8035(15) yes
P1 C1 1.8298(16) yes
O2 C3 1.3561(17) ?
O2 H2O 0.81(3) ?
C1 C2 1.502(2) ?
C1 H2 0.941(19) ?
C1 H1A 0.97(2) ?
C2 C7 1.389(2) ?
C2 C3 1.398(2) ?
C3 C4 1.391(2) ?
C4 C5 1.388(2) ?
C4 H4 0.984(18) ?
C5 C6 1.379(3) ?
C5 H5 0.97(2) ?
C14 C15 1.388(2) ?
C14 C19 1.394(2) ?
C6 C7 1.387(3) ?
C6 H6 0.98(2) ?
C19 C18 1.389(2) ?
C19 H19 0.921(18) ?
C7 H7 0.995(18) ?
C8 C13 1.389(2) ?
C8 C9 1.395(2) ?
C16 C17 1.380(3) ?
C16 C15 1.386(2) ?
C16 H16 0.92(2) ?
C15 H15 0.914(19) ?
C18 C17 1.377(3) ?
C18 H18 0.93(2) ?
C9 C10 1.381(3) ?
C9 H9 1.04(3) ?
C17 H17 0.96(2) ?
C13 C12 1.382(2) ?
C13 H13 0.99(2) ?
C10 C11 1.377(3) ?
C10 H10 0.98(3) ?
C12 C11 1.378(3) ?
C12 H12 1.02(3) ?
C11 H11 0.89(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2O O1 3_665 0.81(2) 1.84(3) 2.6513(16) 172(2) yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
O1 P1 C1 C2 17.83(13) yes
C14 P1 C1 C2 -104.50(11) ?
C8 P1 C1 C2 142.00(11) ?
P1 C1 C2 C7 106.83(14) ?
P1 C1 C2 C3 -74.49(15) ?
C7 C2 C3 O2 175.85(12) ?
C1 C2 C3 O2 -2.87(19) ?
C7 C2 C3 C4 -2.2(2) ?
C1 C2 C3 C4 179.12(13) ?
O2 C3 C4 C5 -176.46(14) ?
C2 C3 C4 C5 1.4(2) ?
C3 C4 C5 C6 0.6(2) ?
O1 P1 C14 C15 12.19(14) yes
C8 P1 C14 C15 -110.40(12) ?
C1 P1 C14 C15 137.42(12) ?
O1 P1 C14 C19 -169.79(12) ?
C8 P1 C14 C19 67.62(14) ?
C1 P1 C14 C19 -44.57(14) ?
C4 C5 C6 C7 -1.9(3) ?
C15 C14 C19 C18 0.6(2) ?
P1 C14 C19 C18 -177.39(13) ?
C5 C6 C7 C2 1.2(2) ?
C3 C2 C7 C6 0.9(2) ?
C1 C2 C7 C6 179.56(14) ?
O1 P1 C8 C13 -101.06(15) ?
C14 P1 C8 C13 19.89(16) ?
C1 P1 C8 C13 133.47(15) ?
O1 P1 C8 C9 74.65(14) yes
C14 P1 C8 C9 -164.41(13) ?
C1 P1 C8 C9 -50.82(14) ?
C17 C16 C15 C14 0.7(3) ?
C19 C14 C15 C16 -1.0(2) ?
P1 C14 C15 C16 177.08(12) ?
C14 C19 C18 C17 0.0(3) ?
C13 C8 C9 C10 -0.5(3) ?
P1 C8 C9 C10 -176.30(15) ?
C19 C18 C17 C16 -0.3(3) ?
C15 C16 C17 C18 -0.1(3) ?
C9 C8 C13 C12 0.2(3) ?
P1 C8 C13 C12 175.84(16) ?
C8 C9 C10 C11 0.4(3) ?
C8 C13 C12 C11 0.2(3) ?
C9 C10 C11 C12 -0.1(4) ?
C13 C12 C11 C10 -0.2(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 696995
