#------------------------------------------------------------------------------
#$Date: 2018-01-18 08:07:00 +0200 (Thu, 18 Jan 2018) $
#$Revision: 205354 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/09/2020944.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_2020944
loop_
_publ_author_name
'Sun, Peili'
'Zhang, Zongyao'
'Luo, Hongxia'
'Zhang, Pu'
'Qin, Yujun'
'Guo, Zhi-Xin'
_publ_section_title
;
 Synthesis, crystal structure and photophysical properties of
 1,4-bis(1,3-diazaazulen-2-yl)benzene: a new π building block
;
_journal_coeditor_code           LF3067
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229617018459
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C22 H14 N4'
_chemical_formula_moiety         'C22 H14 N4'
_chemical_formula_sum            'C22 H14 N4'
_chemical_formula_weight         334.37
_chemical_name_common
;
1,4-Bis(1,3-diazaazulen-2-yl)benzene
;
_chemical_name_systematic
;
2-[4-(Cyclohepta[d]imidazol-2-yl)phenyl]cyclohepta[d]imidazole
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.226(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   3.7610(3)
_cell_length_b                   13.2538(9)
_cell_length_c                   18.8657(19)
_cell_measurement_reflns_used    868
_cell_measurement_temperature    105.6
_cell_measurement_theta_max      29.0505
_cell_measurement_theta_min      3.2320
_cell_volume                     940.19(14)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2011)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2011)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2011)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      105.6
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Agilent Xcalibur Eos Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            3520
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.26
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2011)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_platon_squeeze_details
;
;
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.196
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1846
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0535
_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)+(0.0762P)²+0.1696P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1457
_refine_ls_wR_factor_ref         0.1551
_reflns_number_gt                1396
_reflns_number_total             1846
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            lf3067sup1.cif
_cod_data_source_block           I
_cod_database_code               2020944
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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_symmetry_multiplicity
N N2 0.1546(4) 0.52343(13) 0.18448(8) 0.0228(4) Uani d . 1 1
N N1 0.2047(4) 0.68447(13) 0.13999(9) 0.0218(4) Uani d . 1 1
C C2 0.3804(5) 0.54193(16) 0.06353(10) 0.0194(5) Uani d . 1 1
C C1 0.2471(5) 0.58368(16) 0.12997(10) 0.0199(5) Uani d . 1 1
C C4 0.3503(5) 0.43798(16) 0.05077(10) 0.0202(5) Uani d . 1 1
H H4 0.2500 0.3965 0.0847 0.024 Uiso calc R 1 1
C C3 0.5311(5) 0.60383(15) 0.01219(10) 0.0206(5) Uani d . 1 1
H H3 0.5522 0.6729 0.0201 0.025 Uiso calc R 1 1
C C7 -0.0754(5) 0.55841(17) 0.30062(11) 0.0288(5) Uani d . 1 1
H H7 -0.0712 0.4894 0.3096 0.035 Uiso calc R 1 1
C C8 -0.1973(5) 0.61972(18) 0.35492(12) 0.0293(5) Uani d . 1 1
H H8 -0.2623 0.5862 0.3960 0.035 Uiso calc R 1 1
C C5 0.0698(5) 0.69108(16) 0.20612(11) 0.0218(5) Uani d . 1 1
C C6 0.0408(5) 0.58873(16) 0.23432(10) 0.0220(5) Uani d . 1 1
C C10 -0.1619(5) 0.79588(17) 0.30496(11) 0.0285(5) Uani d . 1 1
H H10 -0.2142 0.8622 0.3171 0.034 Uiso calc R 1 1
C C11 -0.0212(5) 0.78228(17) 0.23809(11) 0.0261(5) Uani d . 1 1
H H11 0.0165 0.8404 0.2117 0.031 Uiso calc R 1 1
C C9 -0.2352(5) 0.72377(18) 0.35631(11) 0.0289(5) Uani d . 1 1
H H9 -0.3238 0.7495 0.3983 0.035 Uiso calc R 1 1
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'
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
C1 N2 C6 . 103.92(17)
C1 N1 C5 . 103.78(17)
C4 C2 C1 . 119.27(17)
C3 C2 C1 . 121.40(19)
C3 C2 C4 . 119.32(17)
N2 C1 N1 . 116.20(16)
N2 C1 C2 . 121.62(19)
N1 C1 C2 . 122.17(18)
C2 C4 H4 . 119.6
C3 C4 C2 3_665 120.73(18)
C3 C4 H4 3_665 119.6
C2 C3 H3 . 120.0
C4 C3 C2 3_665 119.95(18)
C4 C3 H3 3_665 120.0
C8 C7 H7 . 116.3
C8 C7 C6 . 127.4(2)
C6 C7 H7 . 116.3
C7 C8 H8 . 115.5
C9 C8 C7 . 129.0(2)
C9 C8 H8 . 115.5
N1 C5 C6 . 107.83(17)
N1 C5 C11 . 123.49(19)
C11 C5 C6 . 128.68(19)
N2 C6 C7 . 123.3(2)
N2 C6 C5 . 108.26(17)
C7 C6 C5 . 128.43(19)
C11 C10 H10 . 115.6
C11 C10 C9 . 128.8(2)
C9 C10 H10 . 115.6
C5 C11 H11 . 116.4
C10 C11 C5 . 127.3(2)
C10 C11 H11 . 116.4
C8 C9 C10 . 130.3(2)
C8 C9 H9 . 114.8
C10 C9 H9 . 114.8
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
N2 C1 . 1.353(3) y
N2 C6 . 1.354(3) y
N1 C1 . 1.359(3) y
N1 C5 . 1.360(3) y
C2 C1 . 1.468(3) y
C2 C4 . 1.403(3) y
C2 C3 . 1.399(3) y
C4 H4 . 0.9300 ?
C4 C3 3_665 1.393(3) y
C3 C4 3_665 1.393(3) ?
C3 H3 . 0.9300 ?
C7 H7 . 0.9300 ?
C7 C8 . 1.393(3) y
C7 C6 . 1.393(3) y
C8 H8 . 0.9300 ?
C8 C9 . 1.387(3) y
C5 C6 . 1.462(3) y
C5 C11 . 1.397(3) y
C10 H10 . 0.9300 ?
C10 C11 . 1.390(3) y
C10 C9 . 1.393(3) y
C11 H11 . 0.9300 ?
C9 H9 . 0.9300 ?
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_4
_geom_torsion
_geom_torsion_publ_flag
N1 C5 C6 N2 . -0.7(2) ?
N1 C5 C6 C7 . 178.37(19) ?
N1 C5 C11 C10 . 179.60(19) ?
C1 N2 C6 C7 . -178.87(18) ?
C1 N2 C6 C5 . 0.2(2) ?
C1 N1 C5 C6 . 0.8(2) ?
C1 N1 C5 C11 . -178.90(19) ?
C1 C2 C4 C3 3_665 178.97(16) ?
C1 C2 C3 C4 3_665 -178.94(16) ?
C4 C2 C1 N2 . 12.0(3) y
C4 C2 C1 N1 . -167.08(18) y
C4 C2 C3 C4 3_665 -0.1(3) ?
C3 C2 C1 N2 . -169.12(17) y
C3 C2 C1 N1 . 11.8(3) y
C3 C2 C4 C3 3_665 0.1(3) ?
C7 C8 C9 C10 . -0.4(4) ?
C8 C7 C6 N2 . -179.84(19) ?
C8 C7 C6 C5 . 1.3(3) ?
C5 N1 C1 N2 . -0.7(2) ?
C5 N1 C1 C2 . 178.42(16) ?
C6 N2 C1 N1 . 0.3(2) ?
C6 N2 C1 C2 . -178.84(16) ?
C6 C7 C8 C9 . 0.6(4) ?
C6 C5 C11 C10 . 0.0(4) ?
C11 C5 C6 N2 . 178.99(19) ?
C11 C5 C6 C7 . -2.0(3) ?
C11 C10 C9 C8 . -1.6(4) ?
C9 C10 C11 C5 . 2.1(4) ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.056 0.000 0.000 96 16 ' '
2 -0.086 0.500 0.500 96 16 ' '

_cod_database_fobs_code 2020944
