#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/64/2206452.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_2206452
loop_
_publ_author_name
'Cui, Jian-Zhong'
'Zhang, Dan'
'Hai-Bin Song'
'Tang, Xiang-Yang'
_publ_section_title
;
 2,2'-(1,4-Phenylenedivinylene)diquinolin-8-ol
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2372
_journal_page_last               o2373
_journal_paper_doi               10.1107/S1600536805020672
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C28 H20 N2 O2'
_chemical_formula_moiety         'C28 H20 N2 O2'
_chemical_formula_sum            'C28 H20 N2 O2'
_chemical_formula_weight         416.46
_chemical_melting_point          499
_chemical_name_systematic
;
2,2'-(1,4-Phenylenedivinylene)diquinolin-8-ol
;
_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
_cell_angle_alpha                90
_cell_angle_beta                 100.740(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.648(6)
_cell_length_b                   5.777(3)
_cell_length_c                   15.852(8)
_cell_measurement_reflns_used    1827
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.62
_cell_volume                     1048.0(9)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_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      294(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5549
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.162
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2142
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0444
_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)+(0.0519P)²+0.0516P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1184
_reflns_number_gt                1323
_reflns_number_total             2142
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk6021.cif
_cod_data_source_block           I
_cod_original_cell_volume        1047.9(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2206452
_cod_database_fobs_code          2206452
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_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_type_symbol
N1 0.53218(12) 0.1645(2) 0.09666(8) 0.0478(4) Uani d . 1 N
O1 0.68802(13) 0.4740(2) 0.05877(9) 0.0710(4) Uani d . 1 O
H1 0.606(2) 0.442(4) 0.0444(14) 0.102(8) Uiso d . 1 H
C1 0.45483(14) 0.0080(3) 0.11203(10) 0.0481(4) Uani d . 1 C
C2 0.48990(16) -0.1873(3) 0.16533(12) 0.0577(5) Uani d . 1 C
H2 0.4352 -0.2986 0.1731 0.069 Uiso calc R 1 H
C3 0.60355(16) -0.2114(3) 0.20496(12) 0.0605(5) Uani d . 1 C
H3 0.6256 -0.3378 0.2406 0.073 Uiso calc R 1 H
C4 0.68787(15) -0.0466(3) 0.19239(11) 0.0507(4) Uani d . 1 C
C5 0.64663(14) 0.1374(3) 0.13568(10) 0.0453(4) Uani d . 1 C
C6 0.72738(15) 0.3031(3) 0.11664(11) 0.0522(5) Uani d . 1 C
C7 0.84278(16) 0.2892(4) 0.15467(13) 0.0656(5) Uani d . 1 C
H7 0.8954 0.3997 0.1424 0.079 Uiso calc R 1 H
C8 0.88171(17) 0.1102(4) 0.21172(13) 0.0718(6) Uani d . 1 C
H8 0.9603 0.1040 0.2373 0.086 Uiso calc R 1 H
C9 0.80795(16) -0.0557(4) 0.23097(12) 0.0658(6) Uani d . 1 C
H9 0.8359 -0.1741 0.2691 0.079 Uiso calc R 1 H
C10 0.33295(15) 0.0498(3) 0.07132(11) 0.0526(5) Uani d . 1 C
H10 0.3191 0.1751 0.0339 0.063 Uiso calc R 1 H
C11 0.23994(15) -0.0724(3) 0.08217(11) 0.0540(5) Uani d . 1 C
H11 0.2535 -0.1971 0.1198 0.065 Uiso calc R 1 H
C12 0.11848(15) -0.0308(3) 0.04094(11) 0.0502(4) Uani d . 1 C
C13 0.08218(16) 0.1650(3) -0.00807(12) 0.0628(5) Uani d . 1 C
H13 0.1366 0.2788 -0.0140 0.075 Uiso calc R 1 H
C14 -0.03270(16) 0.1941(3) -0.04796(12) 0.0623(5) Uani d . 1 C
H14 -0.0535 0.3267 -0.0805 0.075 Uiso calc R 1 H
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
C1 N1 C5 . . 118.34(15) yes
C6 O1 H1 . . 102.3(14) ?
N1 C1 C2 . . 121.21(16) yes
N1 C1 C10 . . 116.15(16) ?
C2 C1 C10 . . 122.63(16) ?
C3 C2 C1 . . 120.10(17) ?
C3 C2 H2 . . 119.9 ?
C1 C2 H2 . . 119.9 ?
C2 C3 C4 . . 120.58(18) ?
C2 C3 H3 . . 119.7 ?
C4 C3 H3 . . 119.7 ?
C3 C4 C5 . . 115.72(16) ?
C3 C4 C9 . . 124.83(18) ?
C5 C4 C9 . . 119.45(17) ?
N1 C5 C6 . . 117.15(16) yes
N1 C5 C4 . . 123.96(16) yes
C6 C5 C4 . . 118.88(15) yes
O1 C6 C7 . . 121.09(17) yes
O1 C6 C5 . . 118.62(15) yes
C7 C6 C5 . . 120.28(17) ?
C6 C7 C8 . . 120.22(19) ?
C6 C7 H7 . . 119.9 ?
C8 C7 H7 . . 119.9 ?
C9 C8 C7 . . 121.76(19) ?
C9 C8 H8 . . 119.1 ?
C7 C8 H8 . . 119.1 ?
C8 C9 C4 . . 119.38(19) ?
C8 C9 H9 . . 120.3 ?
C4 C9 H9 . . 120.3 ?
C11 C10 C1 . . 126.90(17) ?
C11 C10 H10 . . 116.5 ?
C1 C10 H10 . . 116.5 ?
C10 C11 C12 . . 126.68(18) ?
C10 C11 H11 . . 116.7 ?
C12 C11 H11 . . 116.7 ?
C13 C12 C14 . 3 116.53(16) ?
C13 C12 C11 . . 123.39(16) ?
C14 C12 C11 3 . 120.06(17) ?
C14 C13 C12 . . 121.49(17) ?
C14 C13 H13 . . 119.3 ?
C12 C13 H13 . . 119.3 ?
C13 C14 C12 . 3 121.98(17) ?
C13 C14 H14 . . 119.0 ?
C12 C14 H14 3 . 119.0 ?
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 . 1.330(2) yes
N1 C5 . 1.370(2) yes
O1 C6 . 1.368(2) yes
O1 H1 . 0.96(2) ?
C1 C2 . 1.423(2) ?
C1 C10 . 1.466(2) ?
C2 C3 . 1.363(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.408(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.417(2) yes
C4 C9 . 1.419(2) ?
C5 C6 . 1.413(2) yes
C6 C7 . 1.369(2) yes
C7 C8 . 1.393(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.359(3) ?
C8 H8 . 0.9300 ?
C9 H9 . 0.9300 ?
C10 C11 . 1.331(2) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.464(2) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.393(3) ?
C12 C14 3 1.394(2) ?
C13 C14 . 1.380(3) ?
C13 H13 . 0.9300 ?
C14 C12 3 1.394(2) ?
C14 H14 . 0.9300 ?
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
O1 H1 N1 0.96(2) 2.06(2) 2.694(2) 121.8(18)
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
C5 N1 C1 C2 . . -2.0(2)
C5 N1 C1 C10 . . 177.77(14)
N1 C1 C2 C3 . . 3.0(3)
C10 C1 C2 C3 . . -176.73(17)
C1 C2 C3 C4 . . -1.3(3)
C2 C3 C4 C5 . . -1.2(2)
C2 C3 C4 C9 . . 179.70(18)
C1 N1 C5 C6 . . 178.54(14)
C1 N1 C5 C4 . . -0.7(2)
C3 C4 C5 N1 . . 2.3(2)
C9 C4 C5 N1 . . -178.56(16)
C3 C4 C5 C6 . . -176.91(15)
C9 C4 C5 C6 . . 2.2(2)
N1 C5 C6 O1 . . -2.3(2)
C4 C5 C6 O1 . . 176.98(15)
N1 C5 C6 C7 . . 178.69(16)
C4 C5 C6 C7 . . -2.0(2)
O1 C6 C7 C8 . . -178.29(17)
C5 C6 C7 C8 . . 0.7(3)
C6 C7 C8 C9 . . 0.5(3)
C7 C8 C9 C4 . . -0.3(3)
C3 C4 C9 C8 . . 177.96(18)
C5 C4 C9 C8 . . -1.1(3)
N1 C1 C10 C11 . . -174.81(17)
C2 C1 C10 C11 . . 5.0(3)
C1 C10 C11 C12 . . -179.59(16)
C10 C11 C12 C13 . . -8.6(3)
C10 C11 C12 C14 . 3 169.87(18)
C14 C12 C13 C14 3 . -0.5(3)
C11 C12 C13 C14 . . 178.03(18)
C12 C13 C14 C12 . 3 0.5(3)
