#------------------------------------------------------------------------------
#$Date: 2019-11-22 19:02:30 +0200 (Fri, 22 Nov 2019) $
#$Revision: 231263 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/63/4516337.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_4516337
loop_
_publ_author_name
'Sun, Hao'
'Wang, Mingliang'
'Wei, Xiang'
'Zhang, Ruimin'
'Wang, Shengzhi'
'Khan, Arshad'
'Usman, Rabia'
'Feng, Qi'
'Du, Man'
'Yu, Fangfang'
'Zhang, Wei'
'Xu, Chunxiang'
_publ_section_title
;
 Understanding Charge-Transfer Interaction Mode in Cocrystals and Solvates
 of 1-Phenyl-3-(pyren-1-yl) Prop-2-en-1-one and TCNQ
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4032
_journal_paper_doi               10.1021/acs.cgd.5b00656
_journal_volume                  15
_journal_year                    2015
_chemical_formula_sum            'C31 H18 N2 O'
_chemical_formula_weight         434.47
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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                 106.33(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.335(3)
_cell_length_b                   10.607(2)
_cell_length_c                   17.974(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     2256.8(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius CAD4'
_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  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0868
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4342
_diffrn_reflns_theta_full        25.40
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_min         1.72
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9923
_exptl_absorpt_correction_T_min  0.9846
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0044(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4141
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1837
_refine_ls_R_factor_gt           0.0701
_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)+(0.0550P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1303
_refine_ls_wR_factor_ref         0.1708
_reflns_number_gt                1709
_reflns_number_total             4141
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            II.cif
_cod_data_source_block           x
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        2256.8(8)
_cod_original_sg_symbol_H-M      P21/C
_cod_database_code               4516337
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
O O 0.7827(2) 0.1486(3) 0.77469(17) 0.1128(11) Uani 1 1 d .
C1 C 0.5671(3) 0.0786(4) 0.7767(2) 0.0860(12) Uani 1 1 d .
H1A H 0.6071 0.1319 0.8159 0.103 Uiso 1 1 calc R
C2 C 0.4667(4) 0.0280(5) 0.7809(3) 0.0999(14) Uani 1 1 d .
H2A H 0.4386 0.0482 0.8223 0.120 Uiso 1 1 calc R
C3 C 0.4083(4) -0.0515(5) 0.7247(3) 0.1074(15) Uani 1 1 d .
H3A H 0.3404 -0.0861 0.7278 0.129 Uiso 1 1 calc R
C4 C 0.4494(4) -0.0809(4) 0.6634(3) 0.1060(15) Uani 1 1 d .
H4A H 0.4100 -0.1367 0.6255 0.127 Uiso 1 1 calc R
C5 C 0.5496(3) -0.0275(4) 0.6578(2) 0.0890(13) Uani 1 1 d .
H5A H 0.5760 -0.0452 0.6153 0.107 Uiso 1 1 calc R
C6 C 0.6099(3) 0.0519(4) 0.7154(2) 0.0693(10) Uani 1 1 d .
C7 C 0.7204(3) 0.1052(4) 0.7146(2) 0.0781(12) Uani 1 1 d .
C8 C 0.7542(3) 0.1075(3) 0.6429(2) 0.0772(11) Uani 1 1 d .
H8A H 0.7009 0.0871 0.5965 0.093 Uiso 1 1 calc R
C9 C 0.8576(3) 0.1374(3) 0.6416(2) 0.0732(11) Uani 1 1 d .
H9A H 0.9079 0.1569 0.6894 0.088 Uiso 1 1 calc R
C10 C 0.9033(3) 0.1439(3) 0.5756(2) 0.0625(10) Uani 1 1 d .
C11 C 0.8347(3) 0.1171(3) 0.5010(3) 0.0765(11) Uani 1 1 d .
H11A H 0.7602 0.0927 0.4947 0.092 Uiso 1 1 calc R
C12 C 0.8734(4) 0.1256(3) 0.4367(2) 0.0796(12) Uani 1 1 d .
H12A H 0.8247 0.1081 0.3880 0.095 Uiso 1 1 calc R
C13 C 0.9845(4) 0.1599(3) 0.4434(2) 0.0693(11) Uani 1 1 d .
C14 C 1.0585(3) 0.1855(3) 0.5185(2) 0.0630(10) Uani 1 1 d .
C15 C 1.0171(3) 0.1766(3) 0.5842(2) 0.0622(10) Uani 1 1 d .
C16 C 1.0267(4) 0.1704(4) 0.3773(2) 0.0874(13) Uani 1 1 d .
H16A H 0.9784 0.1550 0.3281 0.105 Uiso 1 1 calc R
C17 C 1.1344(5) 0.2018(4) 0.3847(3) 0.0966(15) Uani 1 1 d .
H17A H 1.1597 0.2075 0.3407 0.116 Uiso 1 1 calc R
C18 C 1.2113(5) 0.2270(3) 0.4594(3) 0.0824(12) Uani 1 1 d .
C19 C 1.1725(4) 0.2183(3) 0.5259(2) 0.0683(11) Uani 1 1 d .
C20 C 1.3244(5) 0.2604(4) 0.4684(3) 0.1009(16) Uani 1 1 d .
H20A H 1.3511 0.2667 0.4251 0.121 Uiso 1 1 calc R
C21 C 1.3959(4) 0.2837(5) 0.5410(4) 0.1146(17) Uani 1 1 d .
H21A H 1.4706 0.3060 0.5463 0.137 Uiso 1 1 calc R
C22 C 1.3582(4) 0.2744(4) 0.6054(3) 0.1021(15) Uani 1 1 d .
H22A H 1.4082 0.2897 0.6539 0.123 Uiso 1 1 calc R
C23 C 1.2477(4) 0.2427(4) 0.6003(3) 0.0767(11) Uani 1 1 d .
C24 C 1.2042(3) 0.2331(4) 0.6645(2) 0.0854(13) Uani 1 1 d .
H24A H 1.2525 0.2479 0.7137 0.102 Uiso 1 1 calc R
C25 C 1.0961(3) 0.2036(4) 0.6581(2) 0.0770(11) Uani 1 1 d .
H25A H 1.0717 0.2004 0.7025 0.092 Uiso 1 1 calc R
N1 N 0.6268(3) 0.3646(4) 0.4729(2) 0.0999(12) Uani 1 1 d .
N2 N 0.8316(3) 0.4724(4) 0.7017(2) 0.1067(13) Uani 1 1 d .
C26 C 0.9864(3) 0.4864(3) 0.4203(2) 0.0617(10) Uani 1 1 d .
H26A H 0.9784 0.4773 0.3675 0.074 Uiso 1 1 calc R
C27 C 0.8982(3) 0.4615(3) 0.44816(19) 0.0617(9) Uani 1 1 d .
H27A H 0.8299 0.4361 0.4142 0.074 Uiso 1 1 calc R
C28 C 0.9072(3) 0.4734(3) 0.5292(2) 0.0557(9) Uani 1 1 d .
C29 C 0.8176(3) 0.4479(3) 0.5579(2) 0.0633(10) Uani 1 1 d .
C30 C 0.7116(4) 0.4030(4) 0.5101(2) 0.0733(12) Uani 1 1 d .
C31 C 0.8246(3) 0.4611(4) 0.6378(3) 0.0748(11) 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 121.2(4) . .
C2 C1 H1A 119.4 . .
C6 C1 H1A 119.4 . .
C3 C2 C1 120.1(4) . .
C3 C2 H2A 120.0 . .
C1 C2 H2A 120.0 . .
C2 C3 C4 120.0(4) . .
C2 C3 H3A 120.0 . .
C4 C3 H3A 120.0 . .
C3 C4 C5 120.2(4) . .
C3 C4 H4A 119.9 . .
C5 C4 H4A 119.9 . .
C6 C5 C4 119.9(4) . .
C6 C5 H5A 120.1 . .
C4 C5 H5A 120.1 . .
C1 C6 C5 118.6(4) . .
C1 C6 C7 119.4(4) . .
C5 C6 C7 122.0(4) . .
O C7 C8 120.5(4) . .
O C7 C6 119.1(4) . .
C8 C7 C6 120.4(4) . .
C9 C8 C7 122.3(4) . .
C9 C8 H8A 118.8 . .
C7 C8 H8A 118.8 . .
C8 C9 C10 128.6(4) . .
C8 C9 H9A 115.7 . .
C10 C9 H9A 115.7 . .
C11 C10 C15 118.0(3) . .
C11 C10 C9 120.3(4) . .
C15 C10 C9 121.6(4) . .
C12 C11 C10 122.3(4) . .
C12 C11 H11A 118.9 . .
C10 C11 H11A 118.9 . .
C11 C12 C13 120.8(4) . .
C11 C12 H12A 119.6 . .
C13 C12 H12A 119.6 . .
C12 C13 C14 119.0(4) . .
C12 C13 C16 121.9(4) . .
C14 C13 C16 119.1(4) . .
C15 C14 C19 121.2(4) . .
C15 C14 C13 119.5(4) . .
C19 C14 C13 119.3(4) . .
C10 C15 C14 120.4(4) . .
C10 C15 C25 123.0(3) . .
C14 C15 C25 116.6(3) . .
C17 C16 C13 121.3(4) . .
C17 C16 H16A 119.3 . .
C13 C16 H16A 119.3 . .
C16 C17 C18 121.1(4) . .
C16 C17 H17A 119.5 . .
C18 C17 H17A 119.5 . .
C20 C18 C19 118.8(5) . .
C20 C18 C17 121.9(5) . .
C19 C18 C17 119.2(4) . .
C18 C19 C14 120.0(4) . .
C18 C19 C23 119.9(4) . .
C14 C19 C23 120.1(4) . .
C21 C20 C18 120.4(5) . .
C21 C20 H20A 119.8 . .
C18 C20 H20A 119.8 . .
C22 C21 C20 120.7(5) . .
C22 C21 H21A 119.7 . .
C20 C21 H21A 119.7 . .
C21 C22 C23 121.6(5) . .
C21 C22 H22A 119.2 . .
C23 C22 H22A 119.2 . .
C22 C23 C24 124.0(5) . .
C22 C23 C19 118.6(4) . .
C24 C23 C19 117.3(4) . .
C25 C24 C23 123.0(4) . .
C25 C24 H24A 118.5 . .
C23 C24 H24A 118.5 . .
C24 C25 C15 121.7(4) . .
C24 C25 H25A 119.2 . .
C15 C25 H25A 119.2 . .
C27 C26 C28 120.9(3) . 3_766
C27 C26 H26A 119.6 . .
C28 C26 H26A 119.6 3_766 .
C26 C27 C28 121.4(3) . .
C26 C27 H27A 119.3 . .
C28 C27 H27A 119.3 . .
C29 C28 C26 120.7(3) . 3_766
C29 C28 C27 121.5(3) . .
C26 C28 C27 117.7(3) 3_766 .
C28 C29 C31 122.2(3) . .
C28 C29 C30 122.5(3) . .
C31 C29 C30 115.2(3) . .
N1 C30 C29 178.4(5) . .
N2 C31 C29 179.1(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O C7 1.225(4) .
C1 C2 1.372(5) .
C1 C6 1.377(4) .
C1 H1A 0.9300 .
C2 C3 1.357(5) .
C2 H2A 0.9300 .
C3 C4 1.372(5) .
C3 H3A 0.9300 .
C4 C5 1.389(5) .
C4 H4A 0.9300 .
C5 C6 1.379(5) .
C5 H5A 0.9300 .
C6 C7 1.479(5) .
C7 C8 1.462(5) .
C8 C9 1.322(4) .
C8 H8A 0.9300 .
C9 C10 1.451(4) .
C9 H9A 0.9300 .
C10 C11 1.399(4) .
C10 C15 1.412(4) .
C11 C12 1.372(5) .
C11 H11A 0.9300 .
C12 C13 1.389(5) .
C12 H12A 0.9300 .
C13 C14 1.427(5) .
C13 C16 1.430(5) .
C14 C15 1.415(4) .
C14 C19 1.418(5) .
C15 C25 1.437(5) .
C16 C17 1.339(5) .
C16 H16A 0.9300 .
C17 C18 1.435(5) .
C17 H17A 0.9300 .
C18 C20 1.403(5) .
C18 C19 1.410(5) .
C19 C23 1.420(5) .
C20 C21 1.376(6) .
C20 H20A 0.9300 .
C21 C22 1.367(5) .
C21 H21A 0.9300 .
C22 C23 1.381(5) .
C22 H22A 0.9300 .
C23 C24 1.408(5) .
C24 C25 1.342(4) .
C24 H24A 0.9300 .
C25 H25A 0.9300 .
N1 C30 1.146(5) .
N2 C31 1.134(4) .
C26 C27 1.347(4) .
C26 C28 1.435(4) 3_766
C26 H26A 0.9300 .
C27 C28 1.435(4) .
C27 H27A 0.9300 .
C28 C29 1.371(4) .
C28 C26 1.435(4) 3_766
C29 C31 1.422(5) .
C29 C30 1.429(5) .
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_4
C6 C1 C2 C3 1.0(7) . .
C1 C2 C3 C4 -0.3(7) . .
C2 C3 C4 C5 -1.3(7) . .
C3 C4 C5 C6 2.2(7) . .
C2 C1 C6 C5 -0.1(6) . .
C2 C1 C6 C7 -178.0(4) . .
C4 C5 C6 C1 -1.5(6) . .
C4 C5 C6 C7 176.3(4) . .
C1 C6 C7 O 15.6(6) . .
C5 C6 C7 O -162.2(4) . .
C1 C6 C7 C8 -163.6(4) . .
C5 C6 C7 C8 18.5(6) . .
O C7 C8 C9 10.5(6) . .
C6 C7 C8 C9 -170.2(4) . .
C7 C8 C9 C10 -179.9(3) . .
C8 C9 C10 C11 0.4(6) . .
C8 C9 C10 C15 -179.4(4) . .
C15 C10 C11 C12 -2.1(5) . .
C9 C10 C11 C12 178.1(3) . .
C10 C11 C12 C13 0.9(6) . .
C11 C12 C13 C14 0.4(5) . .
C11 C12 C13 C16 -179.5(3) . .
C12 C13 C14 C15 -0.6(5) . .
C16 C13 C14 C15 179.3(3) . .
C12 C13 C14 C19 178.9(3) . .
C16 C13 C14 C19 -1.2(5) . .
C11 C10 C15 C14 1.9(5) . .
C9 C10 C15 C14 -178.3(3) . .
C11 C10 C15 C25 -178.7(3) . .
C9 C10 C15 C25 1.1(5) . .
C19 C14 C15 C10 180.0(3) . .
C13 C14 C15 C10 -0.6(5) . .
C19 C14 C15 C25 0.5(5) . .
C13 C14 C15 C25 179.9(3) . .
C12 C13 C16 C17 -179.1(4) . .
C14 C13 C16 C17 1.0(6) . .
C13 C16 C17 C18 -0.4(6) . .
C16 C17 C18 C20 -179.9(4) . .
C16 C17 C18 C19 0.0(6) . .
C20 C18 C19 C14 179.6(3) . .
C17 C18 C19 C14 -0.2(5) . .
C20 C18 C19 C23 -0.3(5) . .
C17 C18 C19 C23 179.9(3) . .
C15 C14 C19 C18 -179.7(3) . .
C13 C14 C19 C18 0.8(5) . .
C15 C14 C19 C23 0.2(5) . .
C13 C14 C19 C23 -179.3(3) . .
C19 C18 C20 C21 0.2(6) . .
C17 C18 C20 C21 -179.9(4) . .
C18 C20 C21 C22 0.2(7) . .
C20 C21 C22 C23 -0.6(7) . .
C21 C22 C23 C24 -179.3(4) . .
C21 C22 C23 C19 0.6(6) . .
C18 C19 C23 C22 -0.1(6) . .
C14 C19 C23 C22 180.0(4) . .
C18 C19 C23 C24 179.8(3) . .
C14 C19 C23 C24 -0.2(5) . .
C22 C23 C24 C25 179.2(4) . .
C19 C23 C24 C25 -0.7(6) . .
C23 C24 C25 C15 1.4(6) . .
C10 C15 C25 C24 179.3(4) . .
C14 C15 C25 C24 -1.3(5) . .
C28 C26 C27 C28 -0.4(5) 3_766 .
C26 C27 C28 C29 -179.8(3) . .
C26 C27 C28 C26 0.4(5) . 3_766
C26 C28 C29 C31 0.8(5) 3_766 .
C27 C28 C29 C31 -179.0(3) . .
C26 C28 C29 C30 -177.6(3) 3_766 .
C27 C28 C29 C30 2.7(5) . .
C28 C29 C30 N1 125(17) . .
C31 C29 C30 N1 -53(17) . .
C28 C29 C31 N2 6(31) . .
C30 C29 C31 N2 -175(100) . .
