#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/12/2211233.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_2211233
loop_
_publ_author_name
'Zuo, Na'
'He, Hong-Wu'
_publ_section_title
2-[(4-Chlorophenyl)hydroxymethyl]-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinan-2-one
_journal_coeditor_code           WN2074
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4864
_journal_page_last               o4865
_journal_paper_doi               10.1107/S1600536806039948
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C18 H20 Cl O4 P'
_chemical_formula_moiety         'C18 H20 Cl O4 P'
_chemical_formula_sum            'C18 H20 Cl O4 P'
_chemical_formula_weight         366.76
_chemical_name_systematic
;
2-[(4-Chlorophenyl)hydroxymethyl]-5,5-dimethyl-4-phenyl-1,3,2-
dioxaphosphorinan-2-one
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 110.475(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.5609(14)
_cell_length_b                   6.4450(9)
_cell_length_c                   14.1161(19)
_cell_measurement_reflns_used    1701
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      19.21
_cell_measurement_theta_min      2.97
_cell_volume                     900.1(2)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART APEX 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  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0630
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6763
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.54
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.229
_refine_ls_abs_structure_details 'Flack (1983), 1711 Friedel pairs'
_refine_ls_abs_structure_Flack   0.11(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3837
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0543
_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)+(0.0477P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1124
_reflns_number_gt                2940
_reflns_number_total             3837
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn2074.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'
_cod_database_code               2211233
_cod_database_fobs_code          2211233
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
C C1 0.7869(4) 0.4345(7) 0.3121(3) 0.0733(12) Uani d . 1
H H1 0.7661 0.3308 0.2632 0.088 Uiso calc R 1
C C2 0.7837(5) 0.3911(11) 0.4070(5) 0.111(2) Uani d . 1
H H2 0.7619 0.2585 0.4223 0.133 Uiso calc R 1
C C3 0.8128(6) 0.5450(14) 0.4785(4) 0.123(3) Uani d . 1
H H3 0.8111 0.5164 0.5426 0.148 Uiso calc R 1
C C4 0.8446(5) 0.7423(12) 0.4556(4) 0.110(2) Uani d . 1
H H4 0.8626 0.8468 0.5040 0.132 Uiso calc R 1
C C5 0.8497(4) 0.7845(8) 0.3611(3) 0.0722(12) Uani d . 1
H H5 0.8727 0.9166 0.3461 0.087 Uiso calc R 1
C C6 0.8206(3) 0.6293(6) 0.2890(3) 0.0522(9) Uani d . 1
C C7 0.8224(3) 0.6693(5) 0.1847(2) 0.0422(8) Uani d . 1
H H7 0.7634 0.5668 0.1390 0.051 Uiso calc R 1
C C8 0.9611(3) 0.6594(5) 0.1718(2) 0.0421(8) Uani d . 1
C C9 1.0204(3) 0.4411(6) 0.1976(3) 0.0562(9) Uani d . 1
H H9A 0.9561 0.3408 0.1586 0.084 Uiso calc R 1
H H9B 1.0407 0.4148 0.2683 0.084 Uiso calc R 1
H H9C 1.1018 0.4309 0.1821 0.084 Uiso calc R 1
C C10 1.0617(3) 0.8184(6) 0.2361(3) 0.0616(11) Uani d . 1
H H10A 1.1420 0.8163 0.2189 0.092 Uiso calc R 1
H H10B 1.0844 0.7848 0.3063 0.092 Uiso calc R 1
H H10C 1.0219 0.9542 0.2234 0.092 Uiso calc R 1
C C11 0.9365(3) 0.6936(5) 0.0603(3) 0.0510(9) Uani d . 1
H H11A 1.0221 0.6851 0.0493 0.061 Uiso calc R 1
H H11B 0.8787 0.5837 0.0214 0.061 Uiso calc R 1
C C12 0.6008(3) 0.8405(5) -0.0450(2) 0.0401(7) Uani d . 1
H H12 0.6069 0.6901 -0.0339 0.048 Uiso calc R 1
C C13 0.5934(3) 0.8872(5) -0.1514(2) 0.0413(7) Uani d . 1
C C14 0.6288(3) 0.7374(6) -0.2082(3) 0.0521(9) Uani d . 1
H H14 0.6537 0.6056 -0.1813 0.062 Uiso calc R 1
C C15 0.6274(4) 0.7821(7) -0.3047(3) 0.0617(10) Uani d . 1
H H15 0.6503 0.6806 -0.3427 0.074 Uiso calc R 1
C C16 0.5921(3) 0.9767(8) -0.3434(3) 0.0604(9) Uani d . 1
C C17 0.5519(4) 1.1255(6) -0.2902(3) 0.0602(10) Uani d . 1
H H17 0.5242 1.2554 -0.3185 0.072 Uiso calc R 1
C C18 0.5530(3) 1.0800(6) -0.1943(2) 0.0517(8) Uani d . 1
H H18 0.5263 1.1807 -0.1580 0.062 Uiso calc R 1
Cl Cl1 0.59736(12) 1.0368(2) -0.46172(8) 0.0987(5) Uani d . 1
O O1 0.8739(2) 0.8931(4) 0.02358(17) 0.0492(6) Uani d . 1
O O2 0.7628(2) 0.8759(3) 0.15361(15) 0.0449(6) Uani d . 1
O O3 0.7338(2) 1.1924(3) 0.04441(18) 0.0519(6) Uani d . 1
O O4 0.4888(2) 0.9201(3) -0.02239(18) 0.0487(6) Uani d D 1
H H4A 0.434(3) 0.830(4) -0.025(3) 0.073 Uiso d D 1
P P1 0.74643(7) 0.96582(13) 0.04676(6) 0.0385(2) Uani 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'
Cl Cl 0.1484 0.1585 '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
C6 C1 C2 120.7(5) ?
C6 C1 H1 119.6 ?
C2 C1 H1 119.6 ?
C3 C2 C1 119.5(5) ?
C3 C2 H2 120.2 ?
C1 C2 H2 120.2 ?
C2 C3 C4 120.3(5) ?
C2 C3 H3 119.9 ?
C4 C3 H3 119.9 ?
C5 C4 C3 120.1(6) ?
C5 C4 H4 119.9 ?
C3 C4 H4 119.9 ?
C4 C5 C6 119.7(5) ?
C4 C5 H5 120.2 ?
C6 C5 H5 120.2 ?
C1 C6 C5 119.7(4) ?
C1 C6 C7 118.9(4) ?
C5 C6 C7 121.5(3) ?
O2 C7 C6 107.3(2) ?
O2 C7 C8 109.1(2) ?
C6 C7 C8 116.6(2) ?
O2 C7 H7 107.8 ?
C6 C7 H7 107.8 ?
C8 C7 H7 107.8 ?
C11 C8 C10 110.5(3) ?
C11 C8 C9 106.7(3) ?
C10 C8 C9 109.5(3) ?
C11 C8 C7 107.0(2) ?
C10 C8 C7 113.3(3) ?
C9 C8 C7 109.7(3) ?
C8 C9 H9A 109.5 ?
C8 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
C8 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
C8 C10 H10A 109.5 ?
C8 C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
C8 C10 H10C 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
O1 C11 C8 112.9(3) ?
O1 C11 H11A 109.0 ?
C8 C11 H11A 109.0 ?
O1 C11 H11B 109.0 ?
C8 C11 H11B 109.0 ?
H11A C11 H11B 107.8 ?
O4 C12 C13 113.2(2) ?
O4 C12 P1 104.02(19) ?
C13 C12 P1 111.0(2) ?
O4 C12 H12 109.5 ?
C13 C12 H12 109.5 ?
P1 C12 H12 109.5 ?
C18 C13 C14 118.4(3) ?
C18 C13 C12 121.1(3) ?
C14 C13 C12 120.4(3) ?
C13 C14 C15 120.7(4) ?
C13 C14 H14 119.7 ?
C15 C14 H14 119.7 ?
C16 C15 C14 119.4(4) ?
C16 C15 H15 120.3 ?
C14 C15 H15 120.3 ?
C15 C16 C17 121.0(3) ?
C15 C16 Cl1 119.6(3) ?
C17 C16 Cl1 119.4(4) ?
C16 C17 C18 119.3(4) ?
C16 C17 H17 120.4 ?
C18 C17 H17 120.4 ?
C17 C18 C13 121.1(4) ?
C17 C18 H18 119.5 ?
C13 C18 H18 119.5 ?
C11 O1 P1 120.48(19) ?
C7 O2 P1 120.84(18) ?
C12 O4 H4A 112(3) ?
O3 P1 O1 111.83(13) yes
O3 P1 O2 111.64(13) yes
O1 P1 O2 106.09(11) yes
O3 P1 C12 112.29(14) yes
O1 P1 C12 107.05(13) yes
O2 P1 C12 107.60(13) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 1.375(6) ?
C1 C2 1.380(6) ?
C1 H1 0.9300 ?
C2 C3 1.371(9) ?
C2 H2 0.9300 ?
C3 C4 1.382(10) ?
C3 H3 0.9300 ?
C4 C5 1.380(6) ?
C4 H4 0.9300 ?
C5 C6 1.383(5) ?
C5 H5 0.9300 ?
C6 C7 1.502(4) ?
C7 O2 1.472(4) ?
C7 C8 1.539(4) ?
C7 H7 0.9800 ?
C8 C11 1.519(4) ?
C8 C10 1.526(5) ?
C8 C9 1.532(5) ?
C9 H9A 0.9600 ?
C9 H9B 0.9600 ?
C9 H9C 0.9600 ?
C10 H10A 0.9600 ?
C10 H10B 0.9600 ?
C10 H10C 0.9600 ?
C11 O1 1.456(4) ?
C11 H11A 0.9700 ?
C11 H11B 0.9700 ?
C12 O4 1.425(3) ?
C12 C13 1.507(4) ?
C12 P1 1.817(3) yes
C12 H12 0.9800 ?
C13 C18 1.383(5) ?
C13 C14 1.387(5) ?
C14 C15 1.388(5) ?
C14 H14 0.9300 ?
C15 C16 1.366(6) ?
C15 H15 0.9300 ?
C16 C17 1.374(5) ?
C16 Cl1 1.735(3) ?
C17 C18 1.380(5) ?
C17 H17 0.9300 ?
C18 H18 0.9300 ?
O1 P1 1.564(2) yes
O2 P1 1.568(2) yes
O3 P1 1.466(2) yes
O4 H4A 0.814(10) ?
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
C11 H11A O1 2_745 0.97 2.57 3.290(4) 131
C12 H12 O4 2_645 0.98 2.29 3.126(4) 143
C9 H9A O3 1_545 0.96 2.52 3.439(4) 159
O4 H4A O3 2_645 0.814(10) 1.913(16) 2.696(3) 161(4)
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
C6 C1 C2 C3 0.8(7)
C1 C2 C3 C4 0.3(8)
C2 C3 C4 C5 -1.2(8)
C3 C4 C5 C6 1.1(7)
C2 C1 C6 C5 -0.9(6)
C2 C1 C6 C7 -179.9(3)
C4 C5 C6 C1 -0.1(6)
C4 C5 C6 C7 178.9(3)
C1 C6 C7 O2 139.3(3)
C5 C6 C7 O2 -39.6(4)
C1 C6 C7 C8 -98.0(4)
C5 C6 C7 C8 83.0(4)
O2 C7 C8 C11 -61.2(3)
C6 C7 C8 C11 177.1(3)
O2 C7 C8 C10 60.8(3)
C6 C7 C8 C10 -60.9(4)
O2 C7 C8 C9 -176.5(2)
C6 C7 C8 C9 61.8(4)
C10 C8 C11 O1 -63.7(3)
C9 C8 C11 O1 177.4(2)
C7 C8 C11 O1 60.0(3)
O4 C12 C13 C18 42.4(4)
P1 C12 C13 C18 -74.1(3)
O4 C12 C13 C14 -138.5(3)
P1 C12 C13 C14 105.0(3)
C18 C13 C14 C15 1.8(5)
C12 C13 C14 C15 -177.3(3)
C13 C14 C15 C16 0.7(5)
C14 C15 C16 C17 -3.1(5)
C14 C15 C16 Cl1 177.2(3)
C15 C16 C17 C18 2.9(5)
Cl1 C16 C17 C18 -177.4(2)
C16 C17 C18 C13 -0.3(5)
C14 C13 C18 C17 -2.0(5)
C12 C13 C18 C17 177.1(3)
C8 C11 O1 P1 -48.8(3)
C6 C7 O2 P1 -178.86(19)
C8 C7 O2 P1 54.0(3)
C11 O1 P1 O3 155.1(2)
C11 O1 P1 O2 33.2(3)
C11 O1 P1 C12 -81.5(3)
C7 O2 P1 O3 -158.9(2)
C7 O2 P1 O1 -36.8(2)
C7 O2 P1 C12 77.5(2)
O4 C12 P1 O3 -54.5(2)
C13 C12 P1 O3 67.5(3)
O4 C12 P1 O1 -177.56(18)
C13 C12 P1 O1 -55.6(2)
O4 C12 P1 O2 68.8(2)
C13 C12 P1 O2 -169.2(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21178380
