#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/06/2240645.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_2240645
loop_
_publ_author_name
'Gao, Lei'
'Ma, Zongshan'
'Yan, Hong'
_publ_section_title
;
 Crystal structure of dimethyl
 2,5-bis[(diphenoxyphosphoryl)oxy]cyclohexa-1,4-diene-1,4-dicarboxylate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o401
_journal_page_last               o402
_journal_paper_doi               10.1107/S2056989015008658
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C34 H30 O12 P2'
_chemical_formula_moiety         'C34 H30 O12 P2'
_chemical_formula_sum            'C34 H30 O12 P2'
_chemical_formula_weight         692.52
_chemical_melting_point_gt       391
_chemical_melting_point_lt       393
_chemical_name_common
1,4-Bis(methoxycarbonyl)-2,5-bis(diphenyloxyphosphoryloxy)cyclohexa-1,4-diene
_chemical_name_systematic
;
Dimethyl
2,5-bis[(diphenoxyphosphoryl)oxy]cyclohexa-1,4-diene-1,4-dicarboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 113.644(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.272(10)
_cell_length_b                   10.629(8)
_cell_length_c                   13.174(10)
_cell_measurement_reflns_used    5446
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      1.7
_cell_volume                     1574(2)
_computing_cell_refinement
;
CrystalClear (Rigaku, 2005)
;
_computing_data_collection
;
CrystalClear (Rigaku, 2005)
;
_computing_data_reduction
;
CrystalClear (Rigaku, 2005)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
CrystalStructure (Rigaku, 2005)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.22
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0999
_diffrn_reflns_av_sigmaI/netI    0.1007
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15948
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.81
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  0.9757
_exptl_absorpt_correction_T_min  0.9600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrystalClear; Rigaku, 2005)
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.616
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3758
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0120P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.0991
_reflns_number_gt                2264
_reflns_number_total             3758
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2331sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2240645
_cod_database_fobs_code          2240645
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y+1/2, z+1/2'
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
_atom_site_symmetry_multiplicity
P P1 0.17401(5) 0.72276(5) 0.24500(4) 0.01714(15) Uani d . 1 1
O O1 0.12748(11) 0.81381(12) 0.31240(10) 0.0189(3) Uani d . 1 1
O O2 0.26861(12) 0.64338(12) 0.34149(11) 0.0211(3) Uani d . 1 1
O O3 0.21532(12) 0.77428(12) 0.16508(10) 0.0194(3) Uani d . 1 1
O O4 0.06126(12) 0.63451(12) 0.19634(10) 0.0187(3) Uani d . 1 1
O O5 -0.16106(13) 0.79217(13) -0.10725(11) 0.0285(4) Uani d . 1 1
O O6 -0.06056(12) 0.82652(13) 0.07360(11) 0.0259(4) Uani d . 1 1
C C1 0.20189(18) 0.91573(18) 0.36916(16) 0.0181(5) Uani d . 1 1
C C2 0.20083(19) 1.02272(19) 0.30979(17) 0.0229(5) Uani d . 1 1
H H2 0.1545 1.0266 0.2323 0.027 Uiso calc R 1 1
C C3 0.2684(2) 1.1239(2) 0.36526(18) 0.0288(6) Uani d . 1 1
H H3 0.2690 1.1986 0.3259 0.035 Uiso calc R 1 1
C C4 0.3353(2) 1.1172(2) 0.47791(18) 0.0310(6) Uani d . 1 1
H H4 0.3818 1.1873 0.5159 0.037 Uiso calc R 1 1
C C5 0.3350(2) 1.0088(2) 0.53572(18) 0.0298(6) Uani d . 1 1
H H5 0.3816 1.0046 0.6132 0.036 Uiso calc R 1 1
C C6 0.26714(19) 0.90613(19) 0.48111(17) 0.0237(5) Uani d . 1 1
H H6 0.2659 0.8313 0.5201 0.028 Uiso calc R 1 1
C C7 0.37059(18) 0.58701(19) 0.33647(16) 0.0193(5) Uani d . 1 1
C C8 0.45474(17) 0.6591(2) 0.31964(15) 0.0221(5) Uani d . 1 1
H H8 0.4432 0.7469 0.3063 0.027 Uiso calc R 1 1
C C9 0.55660(19) 0.6006(2) 0.32263(17) 0.0294(6) Uani d . 1 1
H H9 0.6158 0.6483 0.3105 0.035 Uiso calc R 1 1
C C10 0.5728(2) 0.4722(2) 0.34328(17) 0.0317(6) Uani d . 1 1
H H10 0.6431 0.4326 0.3455 0.038 Uiso calc R 1 1
C C11 0.4874(2) 0.4024(2) 0.36046(17) 0.0290(6) Uani d . 1 1
H H11 0.4987 0.3147 0.3747 0.035 Uiso calc R 1 1
C C12 0.38516(19) 0.46028(19) 0.35698(17) 0.0247(5) Uani d . 1 1
H H12 0.3256 0.4128 0.3687 0.030 Uiso calc R 1 1
C C13 0.02855(17) 0.57494(18) 0.09354(16) 0.0173(5) Uani d . 1 1
C C14 -0.04157(18) 0.62776(18) -0.00080(16) 0.0167(5) Uani d . 1 1
C C15 -0.07850(18) 0.55461(17) -0.10704(15) 0.0186(5) Uani d . 1 1
H H15A -0.1664 0.5490 -0.1412 0.022 Uiso calc R 1 1
H H15B -0.0532 0.6015 -0.1588 0.022 Uiso calc R 1 1
C C16 -0.09356(18) 0.75651(19) -0.01748(16) 0.0196(5) Uani d . 1 1
C C17 -0.11425(19) 0.95035(18) 0.05728(18) 0.0302(6) Uani d . 1 1
H H17A -0.0905 0.9985 0.0061 0.045 Uiso calc R 1 1
H H17B -0.0876 0.9943 0.1286 0.045 Uiso calc R 1 1
H H17C -0.2011 0.9420 0.0262 0.045 Uiso calc R 1 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 P1 O2 . . 101.02(7) no
O1 P1 O3 . . 119.47(8) no
O1 P1 O4 . . 97.92(8) no
O2 P1 O3 . . 115.41(9) no
O2 P1 O4 . . 104.54(8) no
O3 P1 O4 . . 115.79(8) no
P1 O1 C1 . . 117.75(13) no
P1 O2 C7 . . 124.62(13) no
P1 O4 C13 . . 121.73(14) no
C16 O6 C17 . . 114.76(16) no
O1 C1 C2 . . 118.23(17) no
O1 C1 C6 . . 118.96(17) no
C2 C1 C6 . . 122.74(19) no
C1 C2 C3 . . 118.52(19) no
C2 C3 C4 . . 120.2(2) no
C3 C4 C5 . . 120.3(2) no
C4 C5 C6 . . 120.3(2) no
C1 C6 C5 . . 118.03(19) no
O2 C7 C8 . . 120.56(18) no
O2 C7 C12 . . 117.1(2) no
C8 C7 C12 . . 122.2(2) no
C7 C8 C9 . . 118.3(2) no
C8 C9 C10 . . 120.3(2) no
C9 C10 C11 . . 120.2(2) no
C10 C11 C12 . . 119.8(2) no
C7 C12 C11 . . 119.3(2) no
O4 C13 C14 . . 122.97(18) no
O4 C13 C15 . 3_565 110.99(16) no
C14 C13 C15 . 3_565 125.99(18) no
C13 C14 C15 . . 119.73(18) no
C13 C14 C16 . . 127.52(18) no
C15 C14 C16 . . 112.75(16) no
C13 C15 C14 3_565 . 114.28(16) no
O5 C16 O6 . . 123.51(19) no
O5 C16 C14 . . 121.40(18) no
O6 C16 C14 . . 115.08(17) no
C1 C2 H2 . . 121.00 no
C3 C2 H2 . . 121.00 no
C2 C3 H3 . . 120.00 no
C4 C3 H3 . . 120.00 no
C3 C4 H4 . . 120.00 no
C5 C4 H4 . . 120.00 no
C4 C5 H5 . . 120.00 no
C6 C5 H5 . . 120.00 no
C1 C6 H6 . . 121.00 no
C5 C6 H6 . . 121.00 no
C7 C8 H8 . . 121.00 no
C9 C8 H8 . . 121.00 no
C8 C9 H9 . . 120.00 no
C10 C9 H9 . . 120.00 no
C9 C10 H10 . . 120.00 no
C11 C10 H10 . . 120.00 no
C10 C11 H11 . . 120.00 no
C12 C11 H11 . . 120.00 no
C7 C12 H12 . . 120.00 no
C11 C12 H12 . . 120.00 no
C14 C15 H15A . . 109.00 no
C14 C15 H15B . . 109.00 no
H15A C15 H15B . . 108.00 no
C13 C15 H15A 3_565 . 109.00 no
C13 C15 H15B 3_565 . 109.00 no
O6 C17 H17A . . 109.00 no
O6 C17 H17B . . 109.00 no
O6 C17 H17C . . 109.00 no
H17A C17 H17B . . 109.00 no
H17A C17 H17C . . 109.00 no
H17B C17 H17C . . 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O1 . 1.5677(19) no
P1 O2 . 1.5785(19) no
P1 O3 . 1.4469(19) no
P1 O4 . 1.579(2) no
O1 C1 . 1.421(3) no
O2 C7 . 1.413(3) no
O4 C13 . 1.400(3) no
O5 C16 . 1.201(3) no
O6 C16 . 1.330(3) no
O6 C17 . 1.449(3) no
C1 C2 . 1.377(3) no
C1 C6 . 1.371(3) no
C2 C3 . 1.376(3) no
C3 C4 . 1.380(3) no
C4 C5 . 1.382(3) no
C5 C6 . 1.386(3) no
C7 C8 . 1.374(3) no
C7 C12 . 1.371(3) no
C8 C9 . 1.383(3) no
C9 C10 . 1.390(3) no
C10 C11 . 1.375(4) no
C11 C12 . 1.382(4) no
C13 C14 . 1.320(3) no
C13 C15 3_565 1.489(3) no
C14 C15 . 1.503(3) no
C14 C16 . 1.489(3) no
C2 H2 . 0.9500 no
C3 H3 . 0.9500 no
C4 H4 . 0.9500 no
C5 H5 . 0.9500 no
C6 H6 . 0.9500 no
C8 H8 . 0.9500 no
C9 H9 . 0.9500 no
C10 H10 . 0.9500 no
C11 H11 . 0.9500 no
C12 H12 . 0.9500 no
C15 H15A . 0.9900 no
C15 H15B . 0.9900 no
C17 H17A . 0.9800 no
C17 H17B . 0.9800 no
C17 H17C . 0.9800 no
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
C2 H2 O5 3_575 0.95 2.56 3.191(4) 124 no
C6 H6 O3 4_565 0.95 2.50 3.345(4) 148 yes
C9 H9 O5 4_665 0.95 2.59 3.405(4) 144 yes
C10 H10 O3 2_645 0.95 2.46 3.381(4) 163 yes
C15 H15B O1 4_564 0.99 2.56 3.409(4) 144 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_site_symmetry_1
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 P1 O1 C1 . . . 75.66(14) no
O3 P1 O1 C1 . . . -52.09(15) no
O4 P1 O1 C1 . . . -177.76(12) no
O1 P1 O2 C7 . . . -151.58(15) no
O3 P1 O2 C7 . . . -21.23(17) no
O4 P1 O2 C7 . . . 107.15(15) no
O1 P1 O4 C13 . . . 149.57(14) no
O2 P1 O4 C13 . . . -106.81(14) no
O3 P1 O4 C13 . . . 21.34(17) no
P1 O1 C1 C2 . . . 81.9(2) no
P1 O1 C1 C6 . . . -101.1(2) no
P1 O2 C7 C8 . . . 59.5(2) no
P1 O2 C7 C12 . . . -125.04(17) no
P1 O4 C13 C14 . . . -88.2(2) no
P1 O4 C13 C15 . . 3_565 94.39(18) no
C17 O6 C16 O5 . . . 1.1(3) no
C17 O6 C16 C14 . . . -178.27(19) no
O1 C1 C2 C3 . . . 177.0(2) no
C6 C1 C2 C3 . . . 0.2(4) no
O1 C1 C6 C5 . . . -177.2(2) no
C2 C1 C6 C5 . . . -0.4(4) no
C1 C2 C3 C4 . . . 0.0(4) no
C2 C3 C4 C5 . . . 0.1(4) no
C3 C4 C5 C6 . . . -0.3(4) no
C4 C5 C6 C1 . . . 0.4(4) no
O2 C7 C8 C9 . . . 175.83(17) no
C12 C7 C8 C9 . . . 0.6(3) no
O2 C7 C12 C11 . . . -175.66(18) no
C8 C7 C12 C11 . . . -0.3(3) no
C7 C8 C9 C10 . . . -0.6(3) no
C8 C9 C10 C11 . . . 0.3(3) no
C9 C10 C11 C12 . . . 0.1(3) no
C10 C11 C12 C7 . . . -0.1(3) no
O4 C13 C14 C15 . . . -176.33(19) no
O4 C13 C14 C16 . . . 2.7(4) no
C15 C13 C14 C15 3_565 . . 0.7(4) no
C15 C13 C14 C16 3_565 . . 179.7(2) no
O4 C13 C15 C14 . 3_565 3_565 176.67(18) no
C14 C13 C15 C14 . 3_565 3_565 -0.7(3) no
C13 C14 C15 C13 . . 3_565 -0.6(3) no
C16 C14 C15 C13 . . 3_565 -179.77(19) no
C13 C14 C16 O5 . . . -176.4(2) no
C13 C14 C16 O6 . . . 2.9(4) no
C15 C14 C16 O5 . . . 2.7(3) no
C15 C14 C16 O6 . . . -177.98(19) no
