#------------------------------------------------------------------------------
#$Date: 2019-09-05 10:38:04 +0300 (Thu, 05 Sep 2019) $
#$Revision: 218006 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/36/7233669.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_7233669
loop_
_publ_author_name
'Gang Liu'
'Mingdi Yang'
'Lianke Wang'
'Jun Zheng'
'Hongping Zhou'
'Jieying Wu'
'Yupeng Tian'
_publ_section_title
;
 Schiff base derivatives containing heterocycles with aggregation-induced
 emission and recognition ability
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              2684
_journal_page_last               2691
_journal_paper_doi               10.1039/C3TC32591A
_journal_volume                  2
_journal_year                    2014
_chemical_formula_sum            'C31 H24 N5 O'
_chemical_formula_weight         482.55
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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                90.00
_cell_angle_beta                 98.054(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.904(4)
_cell_length_b                   9.7529(17)
_cell_length_c                   11.323(2)
_cell_measurement_temperature    291(2)
_cell_volume                     2613.7(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18153
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         0.86
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_correction_T_min  0.9825
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1012
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         4617
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0536
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1211P)²+0.1272P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1592
_refine_ls_wR_factor_ref         0.1968
_reflns_number_gt                3003
_reflns_number_total             4617
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2014-2-2684-2.cif
_cod_data_source_block           aa
_cod_original_cell_volume        2613.8(8)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7233669
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_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
C1 C 0.08273(16) 0.5685(4) 0.5336(3) 0.0927(10) Uani 1 1 d . . .
H1 H 0.0638 0.4894 0.5509 0.111 Uiso 1 1 calc R . .
C2 C 0.0621(2) 0.6944(5) 0.5598(3) 0.1243(16) Uani 1 1 d . . .
H2 H 0.0289 0.7002 0.5939 0.149 Uiso 1 1 calc R . .
C3 C 0.0896(2) 0.8099(5) 0.5363(4) 0.1255(18) Uani 1 1 d . . .
H3 H 0.0757 0.8951 0.5552 0.151 Uiso 1 1 calc R . .
C4 C 0.13781(19) 0.8013(4) 0.4845(5) 0.1330(18) Uani 1 1 d . . .
H4 H 0.1568 0.8807 0.4680 0.160 Uiso 1 1 calc R . .
C5 C 0.15846(14) 0.6739(3) 0.4566(4) 0.1060(13) Uani 1 1 d . . .
H5 H 0.1910 0.6681 0.4204 0.127 Uiso 1 1 calc R . .
C6 C 0.13129(11) 0.5587(3) 0.4819(2) 0.0632(7) Uani 1 1 d . . .
C7 C 0.08424(12) 0.3957(3) 0.2760(2) 0.0749(8) Uani 1 1 d . . .
H7 H 0.0903 0.4865 0.2564 0.090 Uiso 1 1 calc R . .
C8 C 0.04604(13) 0.3201(4) 0.2040(3) 0.0852(9) Uani 1 1 d . . .
H8 H 0.0264 0.3594 0.1356 0.102 Uiso 1 1 calc R . .
C9 C 0.03602(12) 0.1849(4) 0.2315(3) 0.0852(9) Uani 1 1 d . . .
H9 H 0.0095 0.1330 0.1826 0.102 Uiso 1 1 calc R . .
C10 C 0.06595(13) 0.1287(3) 0.3321(3) 0.0873(9) Uani 1 1 d . . .
H10 H 0.0600 0.0374 0.3507 0.105 Uiso 1 1 calc R . .
C11 C 0.10474(11) 0.2054(3) 0.4065(3) 0.0722(8) Uani 1 1 d . . .
H11 H 0.1242 0.1662 0.4751 0.087 Uiso 1 1 calc R . .
C12 C 0.11463(10) 0.3406(3) 0.3786(2) 0.0573(6) Uani 1 1 d . . .
C13 C 0.20336(10) 0.3788(2) 0.5153(2) 0.0570(6) Uani 1 1 d . . .
C14 C 0.23291(10) 0.2713(2) 0.4714(2) 0.0600(7) Uani 1 1 d . . .
H14 H 0.2175 0.2271 0.4016 0.072 Uiso 1 1 calc R . .
C15 C 0.22814(12) 0.4412(3) 0.6211(2) 0.0701(8) Uani 1 1 d . . .
H15 H 0.2091 0.5120 0.6533 0.084 Uiso 1 1 calc R . .
C16 C 0.27989(11) 0.4007(3) 0.6786(2) 0.0655(7) Uani 1 1 d . . .
H16 H 0.2953 0.4449 0.7484 0.079 Uiso 1 1 calc R . .
C17 C 0.28456(10) 0.2295(2) 0.5297(2) 0.0584(6) Uani 1 1 d . . .
H17 H 0.3031 0.1567 0.4991 0.070 Uiso 1 1 calc R . .
C18 C 0.30963(10) 0.2938(2) 0.6335(2) 0.0509(6) Uani 1 1 d . . .
C19 C 0.36419(9) 0.2514(2) 0.6974(2) 0.0486(6) Uani 1 1 d . . .
C20 C 0.43913(9) 0.2350(2) 0.82809(19) 0.0457(5) Uani 1 1 d . . .
C21 C 0.44322(9) 0.1341(2) 0.7416(2) 0.0482(5) Uani 1 1 d . . .
C22 C 0.48198(9) 0.2496(2) 0.9240(2) 0.0492(6) Uani 1 1 d . . .
H22 H 0.4798 0.3169 0.9814 0.059 Uiso 1 1 calc R . .
C23 C 0.48958(10) 0.0468(2) 0.7487(2) 0.0582(6) Uani 1 1 d . . .
H23 H 0.4921 -0.0201 0.6911 0.070 Uiso 1 1 calc R . .
C24 C 0.53130(10) 0.0629(3) 0.8435(2) 0.0584(6) Uani 1 1 d . . .
H24 H 0.5629 0.0065 0.8494 0.070 Uiso 1 1 calc R . .
C25 C 0.52779(9) 0.1620(2) 0.9322(2) 0.0500(6) Uani 1 1 d . . .
C26 C 0.60606(10) 0.0911(2) 1.0662(2) 0.0581(6) Uani 1 1 d . . .
H26 H 0.6035 0.0080 1.0255 0.070 Uiso 1 1 calc R . .
C27 C 0.65071(10) 0.1080(2) 1.1674(2) 0.0550(6) Uani 1 1 d . . .
C28 C 0.64762(13) 0.2042(3) 1.2553(3) 0.0740(8) Uani 1 1 d . . .
H28 H 0.6168 0.2632 1.2511 0.089 Uiso 1 1 calc R . .
C29 C 0.69665(12) 0.0241(3) 1.1789(3) 0.0796(8) Uani 1 1 d . . .
H29 H 0.6999 -0.0434 1.1222 0.096 Uiso 1 1 calc R . .
C30 C 0.69038(16) 0.2118(4) 1.3488(3) 0.0920(10) Uani 1 1 d . . .
H30 H 0.6874 0.2771 1.4074 0.110 Uiso 1 1 calc R . .
C31 C 0.73881(14) 0.0403(4) 1.2765(4) 0.0993(11) Uani 1 1 d . . .
H31 H 0.7704 -0.0163 1.2818 0.119 Uiso 1 1 calc R . .
H100 H 0.3880(14) 0.465(4) 0.900(3) 0.118(13) Uiso 1 1 d . . .
H101 H 0.4020(13) 0.597(4) 0.947(3) 0.096(11) Uiso 1 1 d . . .
N1 N 0.15201(8) 0.4257(2) 0.45448(19) 0.0638(6) Uani 1 1 d . . .
N2 N 0.38932(8) 0.30790(18) 0.79793(18) 0.0521(5) Uani 1 1 d . . .
N3 N 0.39516(8) 0.14574(19) 0.65940(16) 0.0506(5) Uani 1 1 d . . .
N4 N 0.57074(8) 0.1841(2) 1.03141(17) 0.0556(5) Uani 1 1 d . . .
N5 N 0.73620(12) 0.1318(4) 1.3617(3) 0.0981(9) Uani 1 1 d . . .
O1 O 0.38560(10) 0.5241(2) 0.96088(18) 0.0797(7) Uani 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
C2 C1 C6 120.4(4) . .
C2 C1 H1 119.8 . .
C6 C1 H1 119.8 . .
C3 C2 C1 120.3(4) . .
C3 C2 H2 119.8 . .
C1 C2 H2 119.8 . .
C2 C3 C4 119.8(4) . .
C2 C3 H3 120.1 . .
C4 C3 H3 120.1 . .
C3 C4 C5 120.0(4) . .
C3 C4 H4 120.0 . .
C5 C4 H4 120.0 . .
C6 C5 C4 120.0(4) . .
C6 C5 H5 120.0 . .
C4 C5 H5 120.0 . .
C5 C6 C1 119.5(3) . .
C5 C6 N1 121.0(3) . .
C1 C6 N1 119.5(3) . .
C8 C7 C12 121.5(3) . .
C8 C7 H7 119.2 . .
C12 C7 H7 119.2 . .
C7 C8 C9 120.4(3) . .
C7 C8 H8 119.8 . .
C9 C8 H8 119.8 . .
C10 C9 C8 118.7(3) . .
C10 C9 H9 120.6 . .
C8 C9 H9 120.6 . .
C9 C10 C11 121.2(3) . .
C9 C10 H10 119.4 . .
C11 C10 H10 119.4 . .
C10 C11 C12 119.9(3) . .
C10 C11 H11 120.1 . .
C12 C11 H11 120.1 . .
C11 C12 C7 118.2(2) . .
C11 C12 N1 122.2(2) . .
C7 C12 N1 119.5(2) . .
C14 C13 C15 117.2(2) . .
C14 C13 N1 121.6(2) . .
C15 C13 N1 121.1(2) . .
C17 C14 C13 121.1(2) . .
C17 C14 H14 119.4 . .
C13 C14 H14 119.4 . .
C16 C15 C13 121.7(2) . .
C16 C15 H15 119.1 . .
C13 C15 H15 119.1 . .
C15 C16 C18 120.8(2) . .
C15 C16 H16 119.6 . .
C18 C16 H16 119.6 . .
C14 C17 C18 121.5(2) . .
C14 C17 H17 119.2 . .
C18 C17 H17 119.2 . .
C17 C18 C16 117.6(2) . .
C17 C18 C19 122.7(2) . .
C16 C18 C19 119.7(2) . .
N2 C19 N3 112.37(19) . .
N2 C19 C18 124.9(2) . .
N3 C19 C18 122.8(2) . .
N2 C20 C22 130.6(2) . .
N2 C20 C21 109.23(19) . .
C22 C20 C21 120.1(2) . .
N3 C21 C23 132.2(2) . .
N3 C21 C20 106.33(19) . .
C23 C21 C20 121.5(2) . .
C25 C22 C20 118.6(2) . .
C25 C22 H22 120.7 . .
C20 C22 H22 120.7 . .
C24 C23 C21 117.5(2) . .
C24 C23 H23 121.2 . .
C21 C23 H23 121.2 . .
C23 C24 C25 122.0(2) . .
C23 C24 H24 119.0 . .
C25 C24 H24 119.0 . .
C22 C25 C24 120.3(2) . .
C22 C25 N4 115.8(2) . .
C24 C25 N4 123.9(2) . .
N4 C26 C27 123.1(2) . .
N4 C26 H26 118.4 . .
C27 C26 H26 118.4 . .
C29 C27 C28 117.7(3) . .
C29 C27 C26 119.8(2) . .
C28 C27 C26 122.4(2) . .
C30 C28 C27 119.1(3) . .
C30 C28 H28 120.4 . .
C27 C28 H28 120.4 . .
C27 C29 C31 119.4(3) . .
C27 C29 H29 120.3 . .
C31 C29 H29 120.3 . .
N5 C30 C28 124.5(3) . .
N5 C30 H30 117.8 . .
C28 C30 H30 117.8 . .
N5 C31 C29 123.5(3) . .
N5 C31 H31 118.3 . .
C29 C31 H31 118.3 . .
C13 N1 C12 122.9(2) . .
C13 N1 C6 119.6(2) . .
C12 N1 C6 116.86(19) . .
C19 N2 C20 105.49(18) . .
C19 N3 C21 106.57(18) . .
C26 N4 C25 120.8(2) . .
C31 N5 C30 115.8(3) . .
H100 O1 H101 109(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.371(5) .
C1 C6 1.374(4) .
C1 H1 0.9300 .
C2 C3 1.349(6) .
C2 H2 0.9300 .
C3 C4 1.368(7) .
C3 H3 0.9300 .
C4 C5 1.389(5) .
C4 H4 0.9300 .
C5 C6 1.349(4) .
C5 H5 0.9300 .
C6 N1 1.438(3) .
C7 C8 1.354(4) .
C7 C12 1.389(4) .
C7 H7 0.9300 .
C8 C9 1.384(5) .
C8 H8 0.9300 .
C9 C10 1.372(4) .
C9 H9 0.9300 .
C10 C11 1.382(4) .
C10 H10 0.9300 .
C11 C12 1.384(4) .
C11 H11 0.9300 .
C12 N1 1.418(3) .
C13 C14 1.394(3) .
C13 C15 1.399(4) .
C13 N1 1.397(3) .
C14 C17 1.378(3) .
C14 H14 0.9300 .
C15 C16 1.373(3) .
C15 H15 0.9300 .
C16 C18 1.398(3) .
C16 H16 0.9300 .
C17 C18 1.391(3) .
C17 H17 0.9300 .
C18 C19 1.460(3) .
C19 N2 1.330(3) .
C19 N3 1.372(3) .
C20 N2 1.388(3) .
C20 C22 1.392(3) .
C20 C21 1.401(3) .
C21 N3 1.378(3) .
C21 C23 1.391(3) .
C22 C25 1.382(3) .
C22 H22 0.9300 .
C23 C24 1.368(3) .
C23 H23 0.9300 .
C24 C25 1.405(3) .
C24 H24 0.9300 .
C25 N4 1.428(3) .
C26 N4 1.264(3) .
C26 C27 1.462(3) .
C26 H26 0.9300 .
C27 C29 1.361(4) .
C27 C28 1.377(4) .
C28 C30 1.366(4) .
C28 H28 0.9300 .
C29 C31 1.397(5) .
C29 H29 0.9300 .
C30 N5 1.336(4) .
C30 H30 0.9300 .
C31 N5 1.322(5) .
C31 H31 0.9300 .
O1 H100 0.91(4) .
O1 H101 0.84(4) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 -0.7(6) . . . .
C1 C2 C3 C4 1.0(7) . . . .
C2 C3 C4 C5 -0.2(7) . . . .
C3 C4 C5 C6 -0.8(6) . . . .
C4 C5 C6 C1 1.1(5) . . . .
C4 C5 C6 N1 -179.6(3) . . . .
C2 C1 C6 C5 -0.3(5) . . . .
C2 C1 C6 N1 -179.6(3) . . . .
C12 C7 C8 C9 0.3(5) . . . .
C7 C8 C9 C10 -0.7(5) . . . .
C8 C9 C10 C11 1.1(5) . . . .
C9 C10 C11 C12 -1.1(5) . . . .
C10 C11 C12 C7 0.7(4) . . . .
C10 C11 C12 N1 177.0(3) . . . .
C8 C7 C12 C11 -0.3(4) . . . .
C8 C7 C12 N1 -176.8(3) . . . .
C15 C13 C14 C17 -0.5(4) . . . .
N1 C13 C14 C17 177.5(2) . . . .
C14 C13 C15 C16 1.2(4) . . . .
N1 C13 C15 C16 -176.7(3) . . . .
C13 C15 C16 C18 -0.6(4) . . . .
C13 C14 C17 C18 -0.9(4) . . . .
C14 C17 C18 C16 1.6(4) . . . .
C14 C17 C18 C19 179.7(2) . . . .
C15 C16 C18 C17 -0.8(4) . . . .
C15 C16 C18 C19 -179.1(2) . . . .
C17 C18 C19 N2 -178.7(2) . . . .
C16 C18 C19 N2 -0.5(4) . . . .
C17 C18 C19 N3 0.7(4) . . . .
C16 C18 C19 N3 178.8(2) . . . .
N2 C20 C21 N3 -0.6(2) . . . .
C22 C20 C21 N3 -179.77(19) . . . .
N2 C20 C21 C23 179.1(2) . . . .
C22 C20 C21 C23 -0.1(3) . . . .
N2 C20 C22 C25 -179.7(2) . . . .
C21 C20 C22 C25 -0.7(3) . . . .
N3 C21 C23 C24 179.6(2) . . . .
C20 C21 C23 C24 0.0(4) . . . .
C21 C23 C24 C25 0.9(4) . . . .
C20 C22 C25 C24 1.6(3) . . . .
C20 C22 C25 N4 178.86(19) . . . .
C23 C24 C25 C22 -1.7(4) . . . .
C23 C24 C25 N4 -178.8(2) . . . .
N4 C26 C27 C29 -160.3(3) . . . .
N4 C26 C27 C28 21.6(4) . . . .
C29 C27 C28 C30 0.3(4) . . . .
C26 C27 C28 C30 178.4(3) . . . .
C28 C27 C29 C31 -1.3(4) . . . .
C26 C27 C29 C31 -179.4(3) . . . .
C27 C28 C30 N5 0.4(5) . . . .
C27 C29 C31 N5 1.7(5) . . . .
C14 C13 N1 C12 27.7(4) . . . .
C15 C13 N1 C12 -154.4(3) . . . .
C14 C13 N1 C6 -161.9(2) . . . .
C15 C13 N1 C6 16.0(4) . . . .
C11 C12 N1 C13 39.7(4) . . . .
C7 C12 N1 C13 -144.0(3) . . . .
C11 C12 N1 C6 -130.9(3) . . . .
C7 C12 N1 C6 45.3(3) . . . .
C5 C6 N1 C13 66.8(4) . . . .
C1 C6 N1 C13 -113.8(3) . . . .
C5 C6 N1 C12 -122.2(3) . . . .
C1 C6 N1 C12 57.1(4) . . . .
N3 C19 N2 C20 -0.5(2) . . . .
C18 C19 N2 C20 178.9(2) . . . .
C22 C20 N2 C19 179.7(2) . . . .
C21 C20 N2 C19 0.6(2) . . . .
N2 C19 N3 C21 0.1(3) . . . .
C18 C19 N3 C21 -179.3(2) . . . .
C23 C21 N3 C19 -179.4(2) . . . .
C20 C21 N3 C19 0.3(2) . . . .
C27 C26 N4 C25 -179.8(2) . . . .
C22 C25 N4 C26 160.8(2) . . . .
C24 C25 N4 C26 -22.0(4) . . . .
C29 C31 N5 C30 -0.9(5) . . . .
C28 C30 N5 C31 -0.1(5) . . . .
