#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/93/2239385.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_2239385
loop_
_publ_author_name
'Hussain, Saghir'
'Deli, Yang'
'Parveen, Shagufta'
'Hao, Xin'
'Zhu, Changjin'
_publ_section_title
;
 Bis[5-methoxy-2-(methoxycarbonyl)phenyl] methylphosphonate
;
_journal_coeditor_code           BH2491
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o269
_journal_paper_doi               10.1107/S1600536814002542
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C19 H21 O9 P'
_chemical_formula_moiety         'C19 H21 O9 P'
_chemical_formula_sum            'C19 H21 O9 P'
_chemical_formula_weight         424.33
_chemical_name_systematic
;
Bis[5-methoxy-2-(methoxycarbonyl)phenyl] methylphosphonate
;
_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-97
_cell_angle_alpha                70.774(9)
_cell_angle_beta                 77.800(9)
_cell_angle_gamma                84.172(10)
_cell_formula_units_Z            2
_cell_length_a                   7.852(2)
_cell_length_b                   10.616(3)
_cell_length_c                   12.200(3)
_cell_measurement_reflns_used    3814
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      31.507
_cell_measurement_theta_min      2.249
_cell_volume                     938.0(4)
_computing_cell_refinement       'CrystalClear (Rigaku, 2008)'
_computing_data_collection       'CrystalClear (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear (Rigaku, 2008)'
_computing_molecular_graphics
;
CrystalStructure (Rigaku, 2008) and DIAMOND (Brandenburg,
1999)
;
_computing_publication_material  'CrystalStructure (Rigaku, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Rigaku AFC10/Saturn724+'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13574
_diffrn_reflns_theta_full        31.00
_diffrn_reflns_theta_max         31.00
_diffrn_reflns_theta_min         2.25
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.9547
_exptl_absorpt_correction_T_min  0.8898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.496
_refine_ls_extinction_coef       0.018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     268
_refine_ls_number_reflns         5875
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0463P)²+0.36P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1024
_reflns_number_gt                5141
_reflns_number_total             5875
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2491sup1.cif
_cod_data_source_block           I
_cod_database_code               2239385
_cod_database_fobs_code          2239385
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_symmetry_multiplicity
P P1 0.33809(4) 0.27109(3) 0.77167(3) 0.01429(8) Uani d . 1 1
O O1 0.32051(13) 0.73969(9) 0.92979(9) 0.0254(2) Uani d . 1 1
O O2 0.05122(13) 0.15477(9) 1.15552(9) 0.0245(2) Uani d . 1 1
O O3 0.29370(14) 0.10828(9) 1.03853(9) 0.0278(2) Uani d . 1 1
O O4 0.42225(11) 0.33306(9) 0.85008(8) 0.01764(17) Uani d . 1 1
O O5 0.40476(11) 0.36743(9) 0.64092(8) 0.01864(18) Uani d . 1 1
O O6 0.14807(11) 0.26036(9) 0.80413(8) 0.01992(18) Uani d . 1 1
O O7 0.12590(14) 0.79574(10) 0.48656(9) 0.0291(2) Uani d . 1 1
O O8 0.33993(14) 0.27659(10) 0.35051(9) 0.0279(2) Uani d . 1 1
O O9 0.32347(16) 0.17592(10) 0.54559(9) 0.0318(2) Uani d . 1 1
C C1 0.33063(15) 0.40112(12) 0.92554(10) 0.0156(2) Uani d . 1 1
C C2 0.36082(15) 0.53541(12) 0.89291(11) 0.0180(2) Uani d . 1 1
H H2 0.4363 0.5776 0.8207 0.022 Uiso calc R 1 1
C C3 0.27920(15) 0.60907(12) 0.96717(11) 0.0177(2) Uani d . 1 1
C C4 0.16437(16) 0.54847(12) 1.07129(11) 0.0183(2) Uani d . 1 1
H H4 0.1058 0.5987 1.1206 0.022 Uiso calc R 1 1
C C5 0.13718(16) 0.41317(12) 1.10167(11) 0.0184(2) Uani d . 1 1
H H5 0.0588 0.3718 1.1728 0.022 Uiso calc R 1 1
C C6 0.22035(15) 0.33527(12) 1.03192(10) 0.0165(2) Uani d . 1 1
C C7 0.24992(19) 0.81449(14) 1.00919(13) 0.0268(3) Uani d . 1 1
H H7A 0.1223 0.8166 1.0222 0.032 Uiso calc R 1 1
H H7B 0.2911 0.9059 0.9747 0.032 Uiso calc R 1 1
H H7C 0.2882 0.7720 1.0848 0.032 Uiso calc R 1 1
C C8 0.19625(16) 0.18952(12) 1.07215(11) 0.0182(2) Uani d . 1 1
C C9 0.0165(2) 0.01386(14) 1.19956(14) 0.0306(3) Uani d . 1 1
H H9A 0.0128 -0.0178 1.1332 0.037 Uiso calc R 1 1
H H9B -0.0959 -0.0006 1.2544 0.037 Uiso calc R 1 1
H H9C 0.1090 -0.0355 1.2409 0.037 Uiso calc R 1 1
C C10 0.47462(17) 0.12702(12) 0.77410(12) 0.0216(2) Uani d . 1 1
H H10A 0.4780 0.0735 0.8562 0.026 Uiso calc R 1 1
H H10B 0.5927 0.1540 0.7321 0.026 Uiso calc R 1 1
H H10C 0.4286 0.0739 0.7354 0.026 Uiso calc R 1 1
C C11 0.30478(14) 0.45119(12) 0.56325(10) 0.0167(2) Uani d . 1 1
C C12 0.25839(15) 0.57749(13) 0.57246(11) 0.0192(2) Uani d . 1 1
H H12 0.2823 0.6012 0.6361 0.023 Uiso calc R 1 1
C C13 0.17609(16) 0.66892(13) 0.48675(12) 0.0210(2) Uani d . 1 1
C C14 0.14194(16) 0.63410(14) 0.39278(12) 0.0225(2) Uani d . 1 1
H H14 0.0855 0.6965 0.3346 0.027 Uiso calc R 1 1
C C15 0.19083(16) 0.50850(13) 0.38535(11) 0.0215(2) Uani d . 1 1
H H15 0.1691 0.4857 0.3206 0.026 Uiso calc R 1 1
C C16 0.27195(15) 0.41295(13) 0.47087(11) 0.0186(2) Uani d . 1 1
C C17 0.1721(2) 0.83997(16) 0.57463(14) 0.0350(3) Uani d . 1 1
H H17A 0.1159 0.7847 0.6532 0.042 Uiso calc R 1 1
H H17B 0.1331 0.9334 0.5626 0.042 Uiso calc R 1 1
H H17C 0.2989 0.8321 0.5686 0.042 Uiso calc R 1 1
C C18 0.31427(16) 0.27628(13) 0.46351(11) 0.0210(2) Uani d . 1 1
C C19 0.3690(2) 0.14795(15) 0.33229(14) 0.0308(3) Uani d . 1 1
H H19A 0.4530 0.0945 0.3797 0.037 Uiso calc R 1 1
H H19B 0.4152 0.1601 0.2484 0.037 Uiso calc R 1 1
H H19C 0.2586 0.1019 0.3564 0.037 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
O6 P1 O5 113.96(5)
O6 P1 O4 114.87(5)
O5 P1 O4 102.31(5)
O6 P1 C10 120.38(6)
O5 P1 C10 101.53(6)
O4 P1 C10 101.30(6)
C3 O1 C7 116.45(10)
C8 O2 C9 115.46(10)
C1 O4 P1 125.45(8)
C11 O5 P1 127.58(8)
C13 O7 C17 117.67(11)
C18 O8 C19 116.33(11)
C2 C1 O4 116.28(10)
C2 C1 C6 121.84(11)
O4 C1 C6 121.81(11)
C1 C2 C3 119.46(11)
C1 C2 H2 120.3
C3 C2 H2 120.3
O1 C3 C4 124.13(11)
O1 C3 C2 115.46(11)
C4 C3 C2 120.41(11)
C5 C4 C3 118.65(11)
C5 C4 H4 120.7
C3 C4 H4 120.7
C4 C5 C6 122.68(11)
C4 C5 H5 118.7
C6 C5 H5 118.7
C5 C6 C1 116.89(11)
C5 C6 C8 120.60(11)
C1 C6 C8 122.47(10)
O1 C7 H7A 109.5
O1 C7 H7B 109.5
H7A C7 H7B 109.5
O1 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
O3 C8 O2 122.46(12)
O3 C8 C6 125.90(12)
O2 C8 C6 111.62(10)
O2 C9 H9A 109.5
O2 C9 H9B 109.5
H9A C9 H9B 109.5
O2 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
P1 C10 H10A 109.5
P1 C10 H10B 109.5
H10A C10 H10B 109.5
P1 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
O5 C11 C12 117.91(11)
O5 C11 C16 119.54(11)
C12 C11 C16 122.11(11)
C11 C12 C13 118.90(12)
C11 C12 H12 120.6
C13 C12 H12 120.6
O7 C13 C12 123.89(12)
O7 C13 C14 115.62(12)
C12 C13 C14 120.48(12)
C15 C14 C13 119.34(12)
C15 C14 H14 120.3
C13 C14 H14 120.3
C14 C15 C16 121.86(12)
C14 C15 H15 119.1
C16 C15 H15 119.1
C11 C16 C15 117.30(12)
C11 C16 C18 122.28(11)
C15 C16 C18 120.39(11)
O7 C17 H17A 109.5
O7 C17 H17B 109.5
H17A C17 H17B 109.5
O7 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
O9 C18 O8 122.93(12)
O9 C18 C16 126.15(12)
O8 C18 C16 110.91(11)
O8 C19 H19A 109.5
O8 C19 H19B 109.5
H19A C19 H19B 109.5
O8 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O6 1.4667(10)
P1 O5 1.5956(10)
P1 O4 1.5984(9)
P1 C10 1.7720(13)
O1 C3 1.3596(15)
O1 C7 1.4375(16)
O2 C8 1.3476(15)
O2 C9 1.4465(16)
O3 C8 1.2099(15)
O4 C1 1.3927(14)
O5 C11 1.3865(14)
O7 C13 1.3633(16)
O7 C17 1.4275(19)
O8 C18 1.3494(16)
O8 C19 1.4428(17)
O9 C18 1.2063(17)
C1 C2 1.3791(17)
C1 C6 1.4048(17)
C2 C3 1.4009(17)
C2 H2 0.9500
C3 C4 1.3914(17)
C4 C5 1.3872(17)
C4 H4 0.9500
C5 C6 1.3977(16)
C5 H5 0.9500
C6 C8 1.4801(17)
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 C12 1.3878(17)
C11 C16 1.3953(17)
C12 C13 1.3939(18)
C12 H12 0.9500
C13 C14 1.3971(19)
C14 C15 1.3764(19)
C14 H14 0.9500
C15 C16 1.4057(18)
C15 H15 0.9500
C16 C18 1.4829(18)
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
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
C7 H7B O3 1_565 0.98 2.52 3.3134(18) 138.1 no
C9 H9A O6 2_557 0.98 2.79 3.3198(18) 114.8 no
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
O6 P1 O4 C1 -14.43(11)
O5 P1 O4 C1 109.57(10)
C10 P1 O4 C1 -145.81(10)
O6 P1 O5 C11 8.28(12)
O4 P1 O5 C11 -116.33(10)
C10 P1 O5 C11 139.24(10)
P1 O4 C1 C2 -112.42(11)
P1 O4 C1 C6 70.66(14)
O4 C1 C2 C3 -177.17(10)
C6 C1 C2 C3 -0.26(18)
C7 O1 C3 C4 5.11(18)
C7 O1 C3 C2 -174.95(11)
C1 C2 C3 O1 178.09(11)
C1 C2 C3 C4 -1.97(18)
O1 C3 C4 C5 -177.96(12)
C2 C3 C4 C5 2.11(18)
C3 C4 C5 C6 -0.03(19)
C4 C5 C6 C1 -2.08(18)
C4 C5 C6 C8 175.82(11)
C2 C1 C6 C5 2.22(17)
O4 C1 C6 C5 178.97(10)
C2 C1 C6 C8 -175.63(11)
O4 C1 C6 C8 1.11(17)
C9 O2 C8 O3 -1.95(18)
C9 O2 C8 C6 179.59(11)
C5 C6 C8 O3 -158.23(13)
C1 C6 C8 O3 19.6(2)
C5 C6 C8 O2 20.16(16)
C1 C6 C8 O2 -162.06(11)
P1 O5 C11 C12 85.25(13)
P1 O5 C11 C16 -102.25(12)
O5 C11 C12 C13 172.42(10)
C16 C11 C12 C13 0.12(18)
C17 O7 C13 C12 4.73(19)
C17 O7 C13 C14 -174.46(12)
C11 C12 C13 O7 -179.55(11)
C11 C12 C13 C14 -0.39(18)
O7 C13 C14 C15 179.04(11)
C12 C13 C14 C15 -0.18(19)
C13 C14 C15 C16 1.06(19)
O5 C11 C16 C15 -171.47(10)
C12 C11 C16 C15 0.71(17)
O5 C11 C16 C18 10.56(17)
C12 C11 C16 C18 -177.27(11)
C14 C15 C16 C11 -1.30(18)
C14 C15 C16 C18 176.71(12)
C19 O8 C18 O9 3.7(2)
C19 O8 C18 C16 -175.42(11)
C11 C16 C18 O9 26.3(2)
C15 C16 C18 O9 -151.63(14)
C11 C16 C18 O8 -154.61(11)
C15 C16 C18 O8 27.48(16)
