#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/06/2210658.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_2210658
loop_
_publ_author_name
'Shan Liu'
'Jing Heng'
'Hong-Jun Zhu'
_publ_section_title
;
 2,5-Dibenzoylterephthalic acid pyridine tetrasolvate
;
_journal_coeditor_code           HK2121
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4631
_journal_page_last               o4633
_journal_paper_doi               10.1107/S1600536806038256
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C22 H14 O6, 4C5 H5 N'
_chemical_formula_moiety         'C22 H14 O6, 4C5 H5 N'
_chemical_formula_sum            'C42 H34 N4 O6'
_chemical_formula_weight         690.73
_chemical_name_systematic
;
2,5-Dibenzoylterephthalic acid pyridine tetrasolvate
;
_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                 90.75(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.990(3)
_cell_length_b                   8.3130(10)
_cell_length_c                   21.437(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      10
_cell_volume                     1780.1(6)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_sigmaI/netI    0.1068
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            3678
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.90
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9827
_exptl_absorpt_correction_T_min  0.9743
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.190
_refine_ls_extinction_coef       0.023(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.2057
_refine_ls_R_factor_gt           0.0757
_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)+(0.05P)²+0.8P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1877
_reflns_number_gt                1385
_reflns_number_total             3476
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2121.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2210658
_cod_database_fobs_code          2210658
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
N N1 0.5613(4) 0.7254(5) 0.43709(19) 0.0666(11) Uani d . 1
N N2 -0.2947(6) 0.2783(6) 0.8317(3) 0.0996(16) Uani d . 1
O O1 -0.0527(3) 0.5204(4) 0.66736(14) 0.0711(10) Uani d . 1
O O2 -0.3107(3) 0.5272(4) 0.58761(15) 0.0744(10) Uani d . 1
O O3 -0.3352(3) 0.3417(4) 0.51340(13) 0.0706(10) Uani d . 1
H H3B -0.4104 0.3332 0.5278 0.106 Uiso calc R 1
C C1 0.6377(6) 0.8460(8) 0.4551(2) 0.0884(17) Uani d . 1
H H1B 0.6122 0.9073 0.4892 0.106 Uiso calc R 1
C C2 0.6015(5) 0.6388(7) 0.3903(3) 0.0896(18) Uani d . 1
H H2A 0.5488 0.5522 0.3776 0.107 Uiso calc R 1
C C3 0.7149(7) 0.6678(10) 0.3592(3) 0.122(3) Uani d . 1
H H3A 0.7384 0.6038 0.3255 0.147 Uiso calc R 1
C C4 0.7930(6) 0.7885(11) 0.3771(3) 0.114(3) Uani d . 1
H H4A 0.8734 0.8073 0.3570 0.137 Uiso calc R 1
C C5 0.7552(6) 0.8845(8) 0.4247(3) 0.101(2) Uani d . 1
H H5A 0.8062 0.9731 0.4367 0.121 Uiso calc R 1
C C6 -0.4843(7) 0.4756(9) 0.7819(3) 0.108(2) Uani d . 1
H H6A -0.5488 0.5440 0.7649 0.129 Uiso calc R 1
C C7 -0.5115(6) 0.3858(8) 0.8325(3) 0.0902(18) Uani d . 1
H H7A -0.5953 0.3903 0.8508 0.108 Uiso calc R 1
C C8 -0.4157(7) 0.2897(7) 0.8559(3) 0.0944(19) Uani d . 1
H H8A -0.4351 0.2281 0.8908 0.113 Uiso calc R 1
C C9 -0.3609(7) 0.4650(8) 0.7562(3) 0.0965(19) Uani d . 1
H H9A -0.3398 0.5247 0.7209 0.116 Uiso calc R 1
C C10 -0.2709(6) 0.3671(8) 0.7825(3) 0.0921(19) Uani d . 1
H H10A -0.1863 0.3615 0.7650 0.111 Uiso calc R 1
C C11 -0.1501(5) 1.1053(6) 0.6513(2) 0.0700(14) Uani d . 1
H H11A -0.1700 1.2134 0.6574 0.084 Uiso calc R 1
C C12 -0.1417(5) 1.0457(6) 0.5919(2) 0.0738(15) Uani d . 1
H H12A -0.1547 1.1132 0.5578 0.089 Uiso calc R 1
C C13 -0.1138(4) 0.8855(5) 0.5831(2) 0.0585(12) Uani d . 1
H H13A -0.1082 0.8445 0.5428 0.070 Uiso calc R 1
C C14 -0.0942(4) 0.7857(5) 0.63338(19) 0.0446(10) Uani d . 1
C C15 -0.1029(4) 0.8473(6) 0.6928(2) 0.0570(12) Uani d . 1
H H15A -0.0906 0.7804 0.7272 0.068 Uiso calc R 1
C C16 -0.1297(5) 1.0079(6) 0.7012(2) 0.0665(14) Uani d . 1
H H16A -0.1339 1.0500 0.7413 0.080 Uiso calc R 1
C C17 -0.0644(4) 0.6116(5) 0.62380(19) 0.0475(11) Uani d . 1
C C18 -0.0358(4) 0.5550(5) 0.55887(17) 0.0420(10) Uani d . 1
C C19 -0.1288(4) 0.4738(5) 0.52174(17) 0.0407(10) Uani d . 1
C C20 -0.2679(4) 0.4501(5) 0.54476(19) 0.0490(11) Uani d . 1
C C21 -0.0917(4) 0.4184(5) 0.46372(18) 0.0462(11) Uani d . 1
H H21A -0.1535 0.3621 0.4393 0.055 Uiso calc R 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'
N N 0.0061 0.0033 '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'
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
C2 N1 C1 . . 117.6(5) yes
C10 N2 C8 . . 116.7(6) yes
N1 C1 C5 . . 122.0(6) yes
N1 C1 H1B . . 119.0 ?
C5 C1 H1B . . 119.0 ?
N1 C2 C3 . . 123.6(6) yes
N1 C2 H2A . . 118.2 ?
C3 C2 H2A . . 118.2 ?
C4 C3 C2 . . 119.4(7) ?
C4 C3 H3A . . 120.3 ?
C2 C3 H3A . . 120.3 ?
C3 C4 C5 . . 119.7(6) ?
C3 C4 H4A . . 120.2 ?
C5 C4 H4A . . 120.2 ?
C4 C5 C1 . . 117.7(6) ?
C4 C5 H5A . . 121.2 ?
C1 C5 H5A . . 121.2 ?
C20 O3 H3B . . 109.5 ?
N2 C8 C7 . . 123.2(6) yes
N2 C10 C9 . . 123.8(6) yes
C16 C11 C12 . . 120.5(5) ?
C16 C11 H11A . . 119.8 ?
C12 C11 H11A . . 119.8 ?
C11 C12 C13 . . 119.6(5) ?
C11 C12 H12A . . 120.2 ?
C13 C12 H12A . . 120.2 ?
C12 C13 C14 . . 120.3(4) ?
C12 C13 H13A . . 119.9 ?
C14 C13 H13A . . 119.9 ?
C15 C14 C13 . . 119.5(4) ?
C15 C14 C17 . . 120.2(4) ?
C13 C14 C17 . . 120.3(4) ?
C14 C15 C16 . . 119.8(5) ?
C14 C15 H15A . . 120.1 ?
C16 C15 H15A . . 120.1 ?
C11 C16 C15 . . 120.3(5) ?
C11 C16 H16A . . 119.8 ?
C15 C16 H16A . . 119.8 ?
O1 C17 C14 . . 121.3(4) yes
O1 C17 C18 . . 120.2(4) yes
C14 C17 C18 . . 118.2(4) ?
C21 C18 C19 3_566 . 119.2(3) ?
C21 C18 C17 3_566 . 117.4(4) ?
C19 C18 C17 . . 123.4(3) ?
C21 C19 C18 . . 119.5(3) ?
C21 C19 C20 . . 121.0(4) ?
C18 C19 C20 . . 119.5(3) ?
O2 C20 O3 . . 125.2(4) yes
O2 C20 C19 . . 121.5(4) yes
O3 C20 C19 . . 113.3(4) yes
C19 C21 C18 . 3_566 121.3(4) ?
C19 C21 H21A . . 119.3 ?
C18 C21 H21A 3_566 . 119.3 ?
C10 C9 C6 . . 118.5(6) ?
C10 C9 H9A . . 120.8 ?
C6 C9 H9A . . 120.8 ?
N2 C8 H8A . . 118.4 ?
C7 C8 H8A . . 118.4 ?
N2 C10 H10A . . 118.1 ?
C9 C10 H10A . . 118.1 ?
C7 C6 C9 . . 119.0(6) ?
C7 C6 H6A . . 120.5 ?
C9 C6 H6A . . 120.5 ?
C8 C7 C6 . . 118.8(6) ?
C8 C7 H7A . . 120.6 ?
C6 C7 H7A . . 120.6 ?
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
N1 C1 . 1.315(6) yes
N1 C2 . 1.303(6) yes
C1 C5 . 1.387(7) ?
C1 H1B . 0.9300 ?
C2 C3 . 1.344(7) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.324(9) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.354(8) ?
C4 H4A . 0.9300 ?
C5 H5A . 0.9300 ?
O1 C17 . 1.207(4) yes
O2 C20 . 1.203(4) yes
O3 C20 . 1.305(5) yes
O3 H3B . 0.8200 ?
C11 C16 . 1.355(6) ?
C11 C12 . 1.368(6) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.374(6) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.372(5) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.377(5) ?
C14 C17 . 1.492(6) ?
C15 C16 . 1.374(6) ?
C15 H15A . 0.9300 ?
C16 H16A . 0.9300 ?
C17 C18 . 1.500(5) ?
C18 C21 3_566 1.386(5) ?
C18 C19 . 1.390(5) ?
C19 C21 . 1.382(5) ?
C19 C20 . 1.494(5) ?
C21 C18 3_566 1.386(5) ?
C21 H21A . 0.9300 ?
C9 C10 . 1.333(7) ?
C9 C6 . 1.360(7) ?
C9 H9A . 0.9300 ?
N2 C8 . 1.325(7) yes
N2 C10 . 1.312(7) yes
C8 C7 . 1.339(7) ?
C8 H8A . 0.9300 ?
C10 H10A . 0.9300 ?
C6 C7 . 1.347(7) ?
C6 H6A . 0.9300 ?
C7 H7A . 0.9300 ?
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
O3 H3B N1 3_566 0.8200 1.7600 2.569(5) 168. yes
C2 H2A O2 3_566 0.9300 2.5900 3.256(6) 129 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_4
_geom_torsion
C2 N1 C1 C5 . . 1.9(8)
C1 N1 C2 C3 . . -1.0(9)
N1 C2 C3 C4 . . 1.3(10)
C2 C3 C4 C5 . . -2.4(11)
C3 C4 C5 C1 . . 3.3(10)
N1 C1 C5 C4 . . -3.0(9)
C16 C11 C12 C13 . . 0.8(8)
C11 C12 C13 C14 . . -0.2(7)
C12 C13 C14 C15 . . 0.1(7)
C12 C13 C14 C17 . . 179.8(4)
C13 C14 C15 C16 . . -0.6(6)
C17 C14 C15 C16 . . 179.7(4)
C12 C11 C16 C15 . . -1.3(7)
C14 C15 C16 C11 . . 1.2(7)
C15 C14 C17 O1 . . 3.0(6)
C13 C14 C17 O1 . . -176.7(4)
C15 C14 C17 C18 . . -171.1(4)
C13 C14 C17 C18 . . 9.2(6)
O1 C17 C18 C21 . 3_566 -94.4(5)
C14 C17 C18 C21 . 3_566 79.8(5)
O1 C17 C18 C19 . . 83.6(5)
C14 C17 C18 C19 . . -102.3(5)
C21 C18 C19 C21 3_566 . 1.4(6)
C17 C18 C19 C21 . . -176.5(4)
C21 C18 C19 C20 3_566 . -177.7(4)
C17 C18 C19 C20 . . 4.4(6)
C21 C19 C20 O2 . . -162.8(4)
C18 C19 C20 O2 . . 16.3(6)
C21 C19 C20 O3 . . 16.3(5)
C18 C19 C20 O3 . . -164.6(3)
C18 C19 C21 C18 . 3_566 -1.4(6)
C20 C19 C21 C18 . 3_566 177.7(4)
C10 N2 C8 C7 . . 0.1(9)
C8 N2 C10 C9 . . -0.5(9)
C6 C9 C10 N2 . . 0.8(10)
C10 C9 C6 C7 . . -0.8(9)
N2 C8 C7 C6 . . -0.1(10)
C9 C6 C7 C8 . . 0.5(10)
