#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/24/2212485.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_2212485
loop_
_publ_author_name
'Samas, Brian'
'Groendyke, Todd'
'Blackburn, Anthony C'
'Godrej, Delara B'
_publ_section_title
;
 2-Hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinan-2-one
 monohydrate
;
_journal_coeditor_code           BT2265
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1276
_journal_page_last               o1278
_journal_paper_doi               10.1107/S1600536807006496
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C11 H15 O4 P, H2 O'
_chemical_formula_moiety         'C11 H15 O4 P, H2 O'
_chemical_formula_sum            'C11 H17 O5 P'
_chemical_formula_weight         260.22
_chemical_melting_point          86.5
_chemical_name_common            '(S)-phencyphos monohydrate'
_chemical_name_systematic
;
2-Hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinan-2-one monohydrate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.017(2)
_cell_length_b                   8.219(3)
_cell_length_c                   25.475(10)
_cell_measurement_reflns_used    983
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.32
_cell_measurement_theta_min      2.60
_cell_volume                     1259.8(8)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'MERCURY (Bruno et al.,  2002)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            23045
_diffrn_reflns_theta_full        28.20
_diffrn_reflns_theta_max         28.20
_diffrn_reflns_theta_min         1.60
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_correction_T_min  0.8611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       columnar
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.227
_refine_ls_abs_structure_details 'Flack (1983), 1213 friedel pairs'
_refine_ls_abs_structure_Flack   -0.03(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3004
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0336
_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)+(0.0515P)²+0.1668P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0846
_reflns_number_gt                2899
_reflns_number_total             3004
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2265.cif
_cod_data_source_block           I
_cod_original_cell_volume        1259.7(8)
_cod_database_code               2212485
_cod_database_fobs_code          2212485
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_type_symbol
_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_refinement_flags
_atom_site_occupancy
P P1 0.04332(6) 0.02404(5) 0.062277(15) 0.02174(11) Uani d . 1
O O4 0.13990(18) 0.06124(12) 0.11859(4) 0.0216(2) Uani d . 1
O O5 0.1019(2) 0.17828(14) 0.02882(4) 0.0273(3) Uani d . 1
O O1 0.5676(2) 0.77298(15) 0.05308(5) 0.0285(2) Uani d . 1
O O2 0.1509(2) -0.12296(15) 0.03994(5) 0.0303(3) Uani d . 1
O O3 -0.20975(18) 0.01727(15) 0.06703(5) 0.0334(3) Uani d D 1
H H99C -0.277(4) -0.0890(17) 0.0584(9) 0.050 Uiso d D 1
C C1 0.0706(3) 0.52093(19) 0.12726(6) 0.0287(3) Uani d . 1
H H1A 0.1057 0.6075 0.1022 0.043 Uiso calc R 1
H H1B 0.1422 0.5445 0.1610 0.043 Uiso calc R 1
H H1C -0.0908 0.5150 0.1322 0.043 Uiso calc R 1
C C2 0.0789(2) 0.21820(17) 0.14251(5) 0.0191(3) Uani d . 1
H H2 -0.0867 0.2230 0.1454 0.023 Uiso calc R 1
C C3 0.0473(3) 0.33505(18) 0.05212(5) 0.0259(3) Uani d . 1
H H3A -0.1161 0.3439 0.0558 0.031 Uiso calc R 1
H H3B 0.0974 0.4230 0.0284 0.031 Uiso calc R 1
C C4 0.1558(3) 0.35813(18) 0.10614(6) 0.0207(3) Uani d . 1
C C5 0.0658(3) 0.30463(19) 0.23693(6) 0.0283(3) Uani d . 1
H H5 -0.0710 0.3579 0.2297 0.034 Uiso calc R 1
C C6 0.4105(3) 0.3620(2) 0.10073(6) 0.0265(3) Uani d . 1
H H6A 0.4532 0.4477 0.0760 0.040 Uiso calc R 1
H H6B 0.4631 0.2566 0.0877 0.040 Uiso calc R 1
H H6C 0.4775 0.3842 0.1351 0.040 Uiso calc R 1
C C7 0.1749(3) 0.21961(19) 0.19719(6) 0.0220(3) Uani d . 1
C C8 0.3730(3) 0.1395(2) 0.20878(6) 0.0297(4) Uani d . 1
H H8 0.4478 0.0799 0.1822 0.036 Uiso calc R 1
C C9 0.1567(4) 0.3118(2) 0.28727(6) 0.0352(4) Uani d . 1
H H9 0.0820 0.3706 0.3141 0.042 Uiso calc R 1
C C10 0.4618(3) 0.1465(2) 0.25917(6) 0.0367(4) Uani d . 1
H H10 0.5965 0.0911 0.2668 0.044 Uiso calc R 1
C C11 0.3549(4) 0.2338(2) 0.29832(6) 0.0378(4) Uani d . 1
H H11 0.4174 0.2400 0.3325 0.045 Uiso calc R 1
H H99A 0.588(4) 0.725(3) 0.0258(9) 0.050(7) Uiso d . 1
H H99B 0.435(5) 0.802(3) 0.0525(9) 0.056(7) Uiso d . 1
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
O2 P1 O3 115.80(7)
O2 P1 O5 110.59(7)
O3 P1 O5 107.25(7)
O2 P1 O4 110.23(7)
O3 P1 O4 107.58(7)
O5 P1 O4 104.76(6)
C2 O4 P1 117.00(9)
C3 O5 P1 116.29(9)
H99A O1 H99B 106(2)
P1 O3 H99C 115.1(14)
C4 C1 H1A 109.5
C4 C1 H1B 109.5
H1A C1 H1B 109.5
C4 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
O4 C2 C7 107.06(11)
O4 C2 C4 109.18(11)
C7 C2 C4 115.63(12)
O4 C2 H2 108.3
C7 C2 H2 108.3
C4 C2 H2 108.3
O5 C3 C4 112.25(12)
O5 C3 H3A 109.2
C4 C3 H3A 109.2
O5 C3 H3B 109.2
C4 C3 H3B 109.2
H3A C3 H3B 107.9
C1 C4 C3 106.29(12)
C1 C4 C6 110.31(12)
C3 C4 C6 110.24(12)
C1 C4 C2 109.81(12)
C3 C4 C2 108.52(12)
C6 C4 C2 111.52(12)
C7 C5 C9 120.26(17)
C7 C5 H5 119.9
C9 C5 H5 119.9
C4 C6 H6A 109.5
C4 C6 H6B 109.5
H6A C6 H6B 109.5
C4 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C8 C7 C5 119.06(15)
C8 C7 C2 121.32(13)
C5 C7 C2 119.61(14)
C10 C8 C7 120.29(16)
C10 C8 H8 119.9
C7 C8 H8 119.9
C11 C9 C5 120.37(16)
C11 C9 H9 119.8
C5 C9 H9 119.8
C11 C10 C8 120.46(18)
C11 C10 H10 119.8
C8 C10 H10 119.8
C9 C11 C10 119.55(16)
C9 C11 H11 120.2
C10 C11 H11 120.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O2 1.4841(13)
P1 O3 1.5284(13)
P1 O5 1.5678(12)
P1 O4 1.5778(12)
O4 C2 1.4731(17)
O5 C3 1.4564(18)
O1 H99A 0.81(3)
O1 H99B 0.83(3)
O3 H99C 0.988(10)
C1 C4 1.531(2)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C7 1.5080(19)
C2 C4 1.548(2)
C2 H2 1.0000
C3 C4 1.535(2)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C6 1.539(2)
C5 C7 1.394(2)
C5 C9 1.395(2)
C5 H5 0.9500
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C7 C8 1.393(2)
C8 C10 1.392(2)
C8 H8 0.9500
C9 C11 1.383(3)
C9 H9 0.9500
C10 C11 1.387(3)
C10 H10 0.9500
C11 H11 0.9500
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
O1 H99B O2 1_565 0.83(3) 1.85(3) 2.670(2) 171(2)
O1 H99A O2 4 0.81(3) 1.91(3) 2.7179(19) 176(2)
C9 H9 O4 3 0.95 2.68 3.625(2) 173.5
O3 H99C O1 1_445 0.988(10) 1.475(11) 2.4395(18) 164(2)
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
O2 P1 O4 C2 169.94(10)
O3 P1 O4 C2 -62.95(11)
O5 P1 O4 C2 50.95(11)
O2 P1 O5 C3 -167.49(10)
O3 P1 O5 C3 65.40(12)
O4 P1 O5 C3 -48.74(12)
P1 O4 C2 C7 175.61(10)
P1 O4 C2 C4 -58.53(14)
P1 O5 C3 C4 56.37(16)
O5 C3 C4 C1 -175.98(13)
O5 C3 C4 C6 64.48(16)
O5 C3 C4 C2 -57.92(16)
O4 C2 C4 C1 173.59(12)
C7 C2 C4 C1 -65.65(17)
O4 C2 C4 C3 57.79(15)
C7 C2 C4 C3 178.55(12)
O4 C2 C4 C6 -63.82(14)
C7 C2 C4 C6 56.93(16)
C9 C5 C7 C8 1.3(2)
C9 C5 C7 C2 -177.73(15)
O4 C2 C7 C8 32.12(19)
C4 C2 C7 C8 -89.78(18)
O4 C2 C7 C5 -148.88(13)
C4 C2 C7 C5 89.22(17)
C5 C7 C8 C10 -0.9(3)
C2 C7 C8 C10 178.12(15)
C7 C5 C9 C11 -0.5(3)
C7 C8 C10 C11 -0.4(3)
C5 C9 C11 C10 -0.8(3)
C8 C10 C11 C9 1.2(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24765067
