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#$Date: 2016-03-26 16:50:14 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180358 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/27/7202764.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7202764
loop_
_publ_author_name
'Wang, Jing'
'Ding, Liyu'
'Yang, Caiqin'
_publ_section_title
;
 Three concomitant polymorphs of 1?:?1
 4,4?-dihydroxybenzophenone/1,2-bis(4-pyridyl)-ethylene: applications
 of hydrothermal method in searching polymorphs
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              591
_journal_paper_doi               10.1039/b701746d
_journal_volume                  9
_journal_year                    2007
_chemical_formula_sum            'C25 H20 N2 O3'
_chemical_formula_weight         396.43
_chemical_name_systematic
;
?
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/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                 96.236(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.9100(16)
_cell_length_b                   5.9777(6)
_cell_length_c                   17.2465(17)
_cell_measurement_temperature    90(1)
_cell_volume                     1938.0(3)
_computing_cell_refinement       SMART
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    XP
_computing_publication_material  XCIF
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90(1)
_diffrn_measured_fraction_theta_full 0.871
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measurement_device_type  'SMART CCD 1000'
_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  0.0468
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17139
_diffrn_reflns_theta_full        32.21
_diffrn_reflns_theta_max         32.21
_diffrn_reflns_theta_min         1.08
_exptl_absorpt_coefficient_mu    0.090
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       0.024(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5965
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0495
_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)+(0.0680P)²+0.4249P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1337
_reflns_number_gt                4270
_reflns_number_total             5965
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b701746d.txt
_cod_data_source_block           p2c
_cod_original_sg_symbol_H-M      P2/c
_cod_database_code               7202764
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.25824(5) 0.68587(16) 0.36289(6) 0.0221(2) Uani 1 1 d . . .
O2 O 0.5000 1.2719(2) 0.2500 0.0383(4) Uani 1 2 d S . .
O3 O 0.23740(5) 0.28203(16) 0.13526(6) 0.0256(2) Uani 1 1 d . . .
O4 O 0.00873(18) -0.3204(3) 0.27159(14) 0.0371(8) Uani 0.50 1 d P . .
H2 H 0.2687(11) 0.165(4) 0.1245(12) 0.056(6) Uiso 1 1 d . . .
C1 C 0.40292(6) 1.0713(2) 0.33378(8) 0.0186(2) Uani 1 1 d . . .
C2 C 0.34336(6) 0.9846(2) 0.36271(7) 0.0189(3) Uani 1 1 d . . .
H2A H 0.3179(8) 1.072(3) 0.3998(9) 0.024(4) Uiso 1 1 d . . .
C3 C 0.31819(6) 0.7738(2) 0.33842(7) 0.0168(2) Uani 1 1 d . . .
C4 C 0.35483(6) 0.6480(2) 0.28738(7) 0.0171(2) Uani 1 1 d . . .
H4A H 0.3363(8) 0.505(3) 0.2699(9) 0.019(4) Uiso 1 1 d . . .
C5 C 0.41590(6) 0.7348(2) 0.26029(7) 0.0160(2) Uani 1 1 d . . .
H5A H 0.4402(7) 0.645(3) 0.2243(8) 0.018(4) Uiso 1 1 d . . .
C6 C 0.44042(6) 0.9487(2) 0.28230(7) 0.0164(2) Uani 1 1 d . . .
C7 C 0.5000 1.0662(3) 0.2500 0.0205(4) Uani 1 2 d S . .
C8 C 0.05974(6) 0.2167(2) 0.19365(7) 0.0174(2) Uani 1 1 d . . .
H8A H 0.0170(7) 0.306(2) 0.1902(8) 0.016(4) Uiso 1 1 d . . .
C9 C 0.11896(7) 0.3098(2) 0.16501(8) 0.0192(3) Uani 1 1 d . . .
H9A H 0.1173(8) 0.458(3) 0.1415(9) 0.019(4) Uiso 1 1 d . . .
C10 C 0.18197(6) 0.1871(2) 0.16644(7) 0.0183(2) Uani 1 1 d . . .
C11 C 0.18574(7) -0.0274(2) 0.19884(7) 0.0188(3) Uani 1 1 d . . .
H11A H 0.2307(8) -0.115(3) 0.2017(9) 0.024(4) Uiso 1 1 d . . .
C12 C 0.12636(7) -0.1186(2) 0.22673(8) 0.0206(3) Uani 1 1 d . . .
H12A H 0.1289(8) -0.268(3) 0.2482(10) 0.031(4) Uiso 1 1 d . . .
C13 C 0.06222(7) 0.0004(2) 0.22429(7) 0.0189(3) Uani 1 1 d . . .
C14 C 0.0000 -0.1170(3) 0.2500 0.0353(5) Uani 1 2 d S . .
C15 C 0.30037(7) 0.7584(2) 0.05883(8) 0.0212(3) Uani 1 1 d . . .
H15A H 0.2503(8) 0.723(3) 0.0601(9) 0.024(4) Uiso 1 1 d . . .
C16 C 0.34461(6) 0.6048(2) 0.02814(8) 0.0196(3) Uani 1 1 d . . .
H16A H 0.3243(8) 0.461(3) 0.0083(9) 0.024(4) Uiso 1 1 d . . .
C17 C 0.41678(6) 0.6554(2) 0.02740(7) 0.0168(2) Uani 1 1 d . . .
C18 C 0.43994(6) 0.8626(2) 0.05773(7) 0.0187(3) Uani 1 1 d . . .
H18A H 0.4905(8) 0.910(3) 0.0588(9) 0.028(4) Uiso 1 1 d . . .
C19 C 0.39176(7) 1.0071(2) 0.08593(8) 0.0197(3) Uani 1 1 d . . .
H19A H 0.4059(7) 1.151(3) 0.1074(8) 0.019(4) Uiso 1 1 d . . .
C20 C 0.46435(6) 0.4944(2) -0.00471(7) 0.0181(2) Uani 1 1 d . . .
H20A H 0.4413(8) 0.378(3) -0.0361(9) 0.026(4) Uiso 1 1 d . . .
C21 C 0.16343(8) 1.2139(2) 0.38719(8) 0.0261(3) Uani 1 1 d . . .
H21A H 0.1909(9) 1.250(3) 0.3449(10) 0.038(5) Uiso 1 1 d . . .
C22 C 0.11423(9) 1.3644(3) 0.40920(11) 0.0410(4) Uani 1 1 d . . .
H22A H 0.1085(10) 1.504(3) 0.3805(12) 0.049(6) Uiso 1 1 d . . .
C23 C 0.07386(8) 1.3106(3) 0.46961(13) 0.0504(6) Uani 1 1 d . . .
C24 C 0.08796(8) 1.1055(3) 0.50588(10) 0.0407(5) Uani 1 1 d . . .
H24A H 0.0632(10) 1.061(3) 0.5476(12) 0.052(6) Uiso 1 1 d . . .
C25 C 0.13791(7) 0.9628(3) 0.47992(8) 0.0239(3) Uani 1 1 d . . .
H25A H 0.1490(9) 0.818(3) 0.5033(10) 0.032(4) Uiso 1 1 d . . .
C26' C 0.02207(12) 1.5039(4) 0.47167(14) 0.0134(4) Uani 0.50 1 d P . .
H26A H 0.0084(9) 1.635(3) 0.4331(11) 0.042(5) Uiso 1 1 d . . .
C26 C 0.01659(14) 1.4110(4) 0.51588(16) 0.0199(5) Uani 0.50 1 d P . .
N1 N 0.32251(6) 0.95824(19) 0.08693(6) 0.0204(2) Uani 1 1 d . . .
N2 N 0.17545(5) 1.01353(18) 0.42074(6) 0.0184(2) Uani 1 1 d . . .
H1A H 0.4196(8) 1.217(3) 0.3499(9) 0.024(4) Uiso 1 1 d . . .
H1 H 0.2335(11) 0.804(4) 0.3861(12) 0.059(6) Uiso 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 O4 C14 72.19(11) 2 . ?
C2 C1 C6 121.39(12) . . ?
C1 C2 C3 119.70(11) . . ?
O1 C3 C2 121.69(11) . . ?
O1 C3 C4 118.39(11) . . ?
C2 C3 C4 119.91(11) . . ?
C5 C4 C3 119.80(11) . . ?
C4 C5 C6 120.82(11) . . ?
C5 C6 C1 118.32(11) . . ?
C5 C6 C7 124.94(11) . . ?
C1 C6 C7 116.52(11) . . ?
O2 C7 C6 118.20(7) . 2_655 ?
O2 C7 C6 118.20(7) . . ?
C6 C7 C6 123.59(15) 2_655 . ?
C9 C8 C13 120.71(11) . . ?
C8 C9 C10 120.19(12) . . ?
O3 C10 C9 117.97(11) . . ?
O3 C10 C11 122.36(11) . . ?
C9 C10 C11 119.67(11) . . ?
C12 C11 C10 119.56(11) . . ?
C11 C12 C13 121.51(12) . . ?
C8 C13 C12 118.32(11) . . ?
C8 C13 C14 123.92(12) . . ?
C12 C13 C14 117.65(12) . . ?
O4 C14 O4 35.6(2) 2 . ?
O4 C14 C13 116.50(17) 2 . ?
O4 C14 C13 117.22(17) . . ?
O4 C14 C13 117.22(17) 2 2 ?
O4 C14 C13 116.50(17) . 2 ?
C13 C14 C13 123.35(17) . 2 ?
N1 C15 C16 123.47(11) . . ?
C15 C16 C17 119.36(12) . . ?
C18 C17 C16 117.05(11) . . ?
C18 C17 C20 122.90(11) . . ?
C16 C17 C20 120.05(11) . . ?
C19 C18 C17 119.64(11) . . ?
N1 C19 C18 123.33(12) . . ?
C20 C20 C17 124.83(15) 3_665 . ?
N2 C21 C22 123.60(15) . . ?
C21 C22 C23 119.76(17) . . ?
C24 C23 C22 116.51(13) . . ?
C24 C23 C26' 138.96(19) . . ?
C22 C23 C26' 104.41(19) . . ?
C24 C23 C26 102.86(19) . . ?
C22 C23 C26 140.6(2) . . ?
C26' C23 C26 36.57(13) . . ?
C25 C24 C23 120.19(15) . . ?
N2 C25 C24 122.99(15) . . ?
C26 C26' C26 88.7(3) 3_586 . ?
C26 C26' C26' 45.1(2) 3_586 3_586 ?
C26 C26' C26' 43.7(2) . 3_586 ?
C26 C26' C23 160.5(3) 3_586 . ?
C26 C26' C23 72.7(3) . . ?
C26' C26' C23 116.2(3) 3_586 . ?
C26' C26 C26' 91.3(3) 3_586 . ?
C26' C26 C26 46.4(2) 3_586 3_586 ?
C26' C26 C26 44.9(2) . 3_586 ?
C26' C26 C23 161.0(3) 3_586 . ?
C26' C26 C23 70.7(3) . . ?
C26 C26 C23 115.4(3) 3_586 . ?
C15 N1 C19 117.13(11) . . ?
C21 N2 C25 116.90(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.3576(14) . ?
O2 C7 1.229(2) . ?
O3 C10 1.3535(14) . ?
O4 O4 0.781(5) 2 ?
O4 C14 1.277(3) . ?
C1 C2 1.3813(17) . ?
C1 C6 1.4019(16) . ?
C2 C3 1.3956(18) . ?
C3 C4 1.3975(17) . ?
C4 C5 1.3923(16) . ?
C5 C6 1.3986(17) . ?
C6 C7 1.4864(14) . ?
C7 C6 1.4864(14) 2_655 ?
C8 C9 1.3885(17) . ?
C8 C13 1.3957(17) . ?
C9 C10 1.3969(17) . ?
C10 C11 1.3977(17) . ?
C11 C12 1.3809(17) . ?
C12 C13 1.4026(17) . ?
C13 C14 1.4787(15) . ?
C14 O4 1.277(3) 2 ?
C14 C13 1.4787(15) 2 ?
C15 N1 1.3393(17) . ?
C15 C16 1.3854(18) . ?
C16 C17 1.3992(16) . ?
C17 C18 1.3965(18) . ?
C17 C20 1.4662(17) . ?
C18 C19 1.3817(18) . ?
C19 N1 1.3437(16) . ?
C20 C20 1.342(2) 3_665 ?
C21 N2 1.3389(17) . ?
C21 C22 1.377(2) . ?
C22 C23 1.394(3) . ?
C23 C24 1.389(3) . ?
C23 C26' 1.518(3) . ?
C23 C26 1.536(3) . ?
C24 C25 1.383(2) . ?
C25 N2 1.3397(16) . ?
C26' C26 0.935(3) 3_586 ?
C26' C26 0.958(3) . ?
C26' C26' 1.353(4) 3_586 ?
C26 C26' 0.935(3) 3_586 ?
C26 C26 1.324(6) 3_586 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N2 0.96(2) 1.81(2) 2.7608(13) 171.6(19) .
O3 H2 N1 0.95(2) 1.77(2) 2.7060(14) 169.9(19) 1_545
