#------------------------------------------------------------------------------
#$Date: 2025-08-22 14:50:14 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301863 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/88/7208858.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_7208858
loop_
_publ_author_name
'Hou, Gui-Ge'
'Zhao, Hui-Juan'
'Sun, Ju-Feng'
'Lin, Dong'
'Dai, Xian-Ping'
'Han, Jing-Tian'
'Zhao, Hui'
_publ_section_title
;
 Synthesis, structure and luminescence of Co-crystals with hexagonal
 channels: arranging disposition and π--π interactions
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              577
_journal_paper_doi               10.1039/c2ce25759a
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C19 H16 N4 O2'
_chemical_formula_weight         332.36
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 97.817(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.599(2)
_cell_length_b                   9.335(3)
_cell_length_c                   23.306(7)
_cell_measurement_reflns_used    764
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      19.520
_cell_measurement_theta_min      2.353
_cell_volume                     1637.9(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'smart APEX'
_diffrn_measurement_method       'phi and omega 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  0.0632
_diffrn_reflns_av_sigmaI/netI    0.0869
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8437
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bar
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3058
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.1358
_refine_ls_R_factor_gt           0.0790
_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)+(0.0481P)²+0.2927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.1699
_reflns_number_gt                1901
_reflns_number_total             3058
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce25759a.txt
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7208858
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1 C 0.1819(5) 1.3530(4) 1.03027(15) 0.0522(9) Uani 1 1 d .
H1 H 0.1531 1.3804 0.9918 0.063 Uiso 1 1 calc R
C2 C 0.2268(6) 1.3571(5) 1.12186(17) 0.0725(12) Uani 1 1 d .
H2 H 0.2346 1.3897 1.1598 0.087 Uiso 1 1 calc R
C3 C 0.2625(5) 1.2218(5) 1.10696(15) 0.0676(11) Uani 1 1 d .
H3 H 0.2995 1.1461 1.1317 0.081 Uiso 1 1 calc R
C4 C 0.2461(4) 1.0963(3) 1.01147(13) 0.0449(8) Uani 1 1 d .
C5 C 0.2973(4) 1.1110(3) 0.95736(13) 0.0466(8) Uani 1 1 d .
H5 H 0.3248 1.2007 0.9437 0.056 Uiso 1 1 calc R
C6 C 0.3072(4) 0.9906(3) 0.92378(14) 0.0467(9) Uani 1 1 d .
H6 H 0.3383 1.0002 0.8867 0.056 Uiso 1 1 calc R
C7 C 0.2720(4) 0.8556(3) 0.94399(14) 0.0443(8) Uani 1 1 d .
C8 C 0.2220(4) 0.8446(4) 0.99899(15) 0.0526(9) Uani 1 1 d .
H8 H 0.1982 0.7550 1.0135 0.063 Uiso 1 1 calc R
C9 C 0.2075(5) 0.9636(4) 1.03191(14) 0.0524(9) Uani 1 1 d .
H9 H 0.1713 0.9548 1.0683 0.063 Uiso 1 1 calc R
C10 C 0.2844(4) 0.7255(3) 0.90860(14) 0.0464(9) Uani 1 1 d .
C11 C 0.2287(5) 0.7192(4) 0.85044(16) 0.0582(10) Uani 1 1 d .
H11 H 0.1830 0.8022 0.8320 0.070 Uiso 1 1 calc R
C12 C 0.3034(5) 0.4867(4) 0.84728(18) 0.0618(10) Uani 1 1 d .
H12 H 0.3088 0.4034 0.8257 0.074 Uiso 1 1 calc R
C13 C 0.3543(5) 0.5985(4) 0.93267(16) 0.0563(10) Uani 1 1 d .
H13 H 0.3973 0.5978 0.9720 0.068 Uiso 1 1 calc R
C14 C 0.8684(5) 0.2342(4) 0.84679(14) 0.0515(9) Uani 1 1 d .
C15 C 0.6856(5) 0.2403(3) 0.83904(13) 0.0486(9) Uani 1 1 d .
H15 H 0.6277 0.3073 0.8594 0.058 Uiso 1 1 calc R
C16 C 0.5879(5) 0.1469(4) 0.80109(13) 0.0492(9) Uani 1 1 d .
C17 C 0.6733(5) 0.0450(4) 0.77162(14) 0.0586(10) Uani 1 1 d .
H17 H 0.6085 -0.0200 0.7470 0.070 Uiso 1 1 calc R
C18 C 0.8572(6) 0.0420(4) 0.77967(15) 0.0673(11) Uani 1 1 d .
H18 H 0.9155 -0.0250 0.7595 0.081 Uiso 1 1 calc R
C19 C 0.9554(5) 0.1350(4) 0.81650(15) 0.0640(11) Uani 1 1 d .
H19 H 1.0788 0.1317 0.8211 0.077 Uiso 1 1 calc R
N1 N 0.1779(4) 1.4396(3) 1.07437(13) 0.0642(9) Uani 1 1 d .
N2 N 0.2326(4) 1.2194(3) 1.04732(11) 0.0485(7) Uani 1 1 d .
N3 N 0.3637(4) 0.4778(3) 0.90320(14) 0.0623(9) Uani 1 1 d .
N4 N 0.2358(4) 0.6016(3) 0.81845(13) 0.0623(9) Uani 1 1 d .
O1 O 0.9707(3) 0.3210(3) 0.88440(11) 0.0706(8) Uani 1 1 d .
H1A H 0.9090 0.3849 0.8953 0.106 Uiso 1 1 calc R
O2 O 0.4071(3) 0.1580(3) 0.79463(10) 0.0641(7) Uani 1 1 d .
H2A H 0.3652 0.1263 0.7629 0.096 Uiso 1 1 calc R
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
N1 C1 N2 112.0(3)
N1 C1 H1 124.0
N2 C1 H1 124.0
C3 C2 N1 111.4(3)
C3 C2 H2 124.3
N1 C2 H2 124.3
C2 C3 N2 105.3(3)
C2 C3 H3 127.4
N2 C3 H3 127.4
C9 C4 C5 120.5(3)
C9 C4 N2 119.1(3)
C5 C4 N2 120.4(3)
C4 C5 C6 118.9(3)
C4 C5 H5 120.5
C6 C5 H5 120.5
C5 C6 C7 121.4(3)
C5 C6 H6 119.3
C7 C6 H6 119.3
C6 C7 C8 118.1(3)
C6 C7 C10 121.9(3)
C8 C7 C10 120.0(3)
C9 C8 C7 120.9(3)
C9 C8 H8 119.6
C7 C8 H8 119.6
C8 C9 C4 120.2(3)
C8 C9 H9 119.9
C4 C9 H9 119.9
C11 C10 C13 114.5(3)
C11 C10 C7 123.7(3)
C13 C10 C7 121.8(3)
N4 C11 C10 124.1(3)
N4 C11 H11 118.0
C10 C11 H11 118.0
N3 C12 N4 127.3(3)
N3 C12 H12 116.4
N4 C12 H12 116.4
N3 C13 C10 124.2(3)
N3 C13 H13 117.9
C10 C13 H13 117.9
O1 C14 C15 122.6(3)
O1 C14 C19 117.2(3)
C15 C14 C19 120.2(3)
C14 C15 C16 120.1(3)
C14 C15 H15 120.0
C16 C15 H15 120.0
O2 C16 C15 117.8(3)
O2 C16 C17 122.0(3)
C15 C16 C17 120.2(3)
C18 C17 C16 118.6(3)
C18 C17 H17 120.7
C16 C17 H17 120.7
C19 C18 C17 121.7(4)
C19 C18 H18 119.1
C17 C18 H18 119.1
C18 C19 C14 119.1(4)
C18 C19 H19 120.4
C14 C19 H19 120.4
C1 N1 C2 104.8(3)
C1 N2 C3 106.5(3)
C1 N2 C4 127.6(3)
C3 N2 C4 125.9(3)
C12 N3 C13 114.8(3)
C12 N4 C11 115.1(3)
C14 O1 H1A 109.5
C16 O2 H2A 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.311(4)
C1 N2 1.349(4)
C1 H1 0.9300
C2 C3 1.347(5)
C2 N1 1.358(4)
C2 H2 0.9300
C3 N2 1.378(4)
C3 H3 0.9300
C4 C9 1.374(4)
C4 C5 1.376(4)
C4 N2 1.433(4)
C5 C6 1.377(4)
C5 H5 0.9300
C6 C7 1.384(4)
C6 H6 0.9300
C7 C8 1.389(4)
C7 C10 1.478(4)
C8 C9 1.362(4)
C8 H8 0.9300
C9 H9 0.9300
C10 C11 1.365(4)
C10 C13 1.386(4)
C11 N4 1.332(4)
C11 H11 0.9300
C12 N3 1.324(4)
C12 N4 1.331(4)
C12 H12 0.9300
C13 N3 1.327(4)
C13 H13 0.9300
C14 O1 1.358(4)
C14 C15 1.378(5)
C14 C19 1.385(5)
C15 C16 1.384(4)
C15 H15 0.9300
C16 O2 1.365(4)
C16 C17 1.385(4)
C17 C18 1.385(5)
C17 H17 0.9300
C18 C19 1.368(5)
C18 H18 0.9300
C19 H19 0.9300
O1 H1A 0.8200
O2 H2A 0.8200
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 H1A N1 0.82 1.94 2.736(4) 165.1 3_677
O2 H2A N4 0.82 1.96 2.761(4) 165.5 2_546
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
N1 C2 C3 N2 -0.7(5)
C9 C4 C5 C6 0.8(5)
N2 C4 C5 C6 -179.4(3)
C4 C5 C6 C7 -1.9(5)
C5 C6 C7 C8 1.4(5)
C5 C6 C7 C10 -179.2(3)
C6 C7 C8 C9 0.3(5)
C10 C7 C8 C9 -179.1(3)
C7 C8 C9 C4 -1.4(5)
C5 C4 C9 C8 0.9(5)
N2 C4 C9 C8 -179.0(3)
C6 C7 C10 C11 -39.7(5)
C8 C7 C10 C11 139.6(4)
C6 C7 C10 C13 140.5(3)
C8 C7 C10 C13 -40.1(5)
C13 C10 C11 N4 1.3(5)
C7 C10 C11 N4 -178.5(3)
C11 C10 C13 N3 -1.8(5)
C7 C10 C13 N3 178.0(3)
O1 C14 C15 C16 -178.5(3)
C19 C14 C15 C16 0.2(5)
C14 C15 C16 O2 -179.5(3)
C14 C15 C16 C17 1.3(5)
O2 C16 C17 C18 178.9(3)
C15 C16 C17 C18 -2.0(5)
C16 C17 C18 C19 1.1(5)
C17 C18 C19 C14 0.4(6)
O1 C14 C19 C18 177.7(3)
C15 C14 C19 C18 -1.1(5)
N2 C1 N1 C2 -0.6(4)
C3 C2 N1 C1 0.8(5)
N1 C1 N2 C3 0.2(4)
N1 C1 N2 C4 177.7(3)
C2 C3 N2 C1 0.3(4)
C2 C3 N2 C4 -177.3(3)
C9 C4 N2 C1 -145.9(3)
C5 C4 N2 C1 34.2(5)
C9 C4 N2 C3 31.1(5)
C5 C4 N2 C3 -148.8(3)
N4 C12 N3 C13 -0.1(6)
C10 C13 N3 C12 1.2(5)
N3 C12 N4 C11 -0.4(6)
C10 C11 N4 C12 -0.3(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139196668
