#------------------------------------------------------------------------------
#$Date: 2018-12-05 01:11:47 +0200 (Wed, 05 Dec 2018) $
#$Revision: 212357 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/26/7122689.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_7122689
loop_
_publ_author_name
'Yamakado, Ryohei'
'Ishibashi, Haruna'
'Motoyoshi, Yukari'
'Yasuda, Nobuhiro'
'Maeda, Hiromitsu'
_publ_section_title
;
 Ion-pairing assemblies based on π-extended dipyrrolylquinoxalines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC08205G
_journal_year                    2018
_chemical_formula_moiety         'C14 H10 N2'
_chemical_formula_sum            'C14 H10 N2'
_chemical_formula_weight         206.24
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      60
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2018-10-05 deposited with the CCDC.
2018-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.909(11)
_cell_length_b                   11.079(5)
_cell_length_c                   7.591(4)
_cell_measurement_reflns_used    2281
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      25.2
_cell_volume                     2010.8(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6714
_diffrn_reflns_theta_full        66.00
_diffrn_reflns_theta_max         66.00
_diffrn_reflns_theta_min         6.84
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  0.8825
_exptl_absorpt_correction_T_min  0.6281
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1728
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0406
_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)+(0.0850P)²+0.4145P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1150
_reflns_number_gt                1632
_reflns_number_total             1728
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc08205g2.cif
_cod_data_source_block           40719m2
_cod_database_code               7122689
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, 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 0.72511(5) 0.47364(11) -0.05319(16) 0.0190(3) Uani 1 1 d .
H1 H 0.7004 0.5346 -0.0946 0.023 Uiso 1 1 calc R
C2 C 0.78215(5) 0.48430(12) -0.08373(16) 0.0209(3) Uani 1 1 d .
H2 H 0.7962 0.5528 -0.1447 0.025 Uiso 1 1 calc R
C3 C 0.81891(5) 0.39568(12) -0.02598(16) 0.0200(3) Uani 1 1 d .
H3 H 0.8580 0.4037 -0.0460 0.024 Uiso 1 1 calc R
C4 C 0.79787(5) 0.29493(11) 0.06160(16) 0.0192(3) Uani 1 1 d .
H4 H 0.8226 0.2331 0.0994 0.023 Uiso 1 1 calc R
C5 C 0.74081(5) 0.28437(11) 0.09399(16) 0.0177(3) Uani 1 1 d .
H5 H 0.7270 0.2156 0.1547 0.021 Uiso 1 1 calc R
C6 C 0.70350(5) 0.37418(10) 0.03794(15) 0.0160(3) Uani 1 1 d .
C7 C 0.64329(5) 0.36771(11) 0.07571(15) 0.0164(3) Uani 1 1 d .
C8 C 0.60118(5) 0.45260(11) 0.05459(16) 0.0185(3) Uani 1 1 d .
H6 H 0.6054 0.5313 0.0067 0.022 Uiso 1 1 calc R
C9 C 0.55099(5) 0.40132(11) 0.11674(16) 0.0181(3) Uani 1 1 d .
H7 H 0.5154 0.4394 0.1182 0.022 Uiso 1 1 calc R
C10 C 0.56265(5) 0.28560(11) 0.17544(16) 0.0158(3) Uani 1 1 d .
C11 C 0.52957(5) 0.18069(11) 0.22808(15) 0.0149(3) Uani 1 1 d .
C12 C 0.52962(5) -0.02835(11) 0.24387(15) 0.0160(3) Uani 1 1 d .
C13 C 0.55863(5) -0.13930(11) 0.24444(17) 0.0202(3) Uani 1 1 d .
H8 H 0.5984 -0.1400 0.2423 0.024 Uiso 1 1 calc R
C14 C 0.52964(6) -0.24586(11) 0.24804(16) 0.0223(3) Uani 1 1 d .
H9 H 0.5494 -0.3203 0.2479 0.027 Uiso 1 1 calc R
N1 N 0.61910(4) 0.26781(9) 0.14908(13) 0.0162(3) Uani 1 1 d .
H10 H 0.6372 0.2011 0.1759 0.019 Uiso 1 1 calc R
N2 N 0.55784(4) 0.07760(9) 0.22446(13) 0.0169(3) 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 0.0181 0.0091 '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 0.0311 0.0180 '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 120.80(11) . .
C2 C1 H1 119.6 . .
C6 C1 H1 119.6 . .
C1 C2 C3 120.58(11) . .
C1 C2 H2 119.7 . .
C3 C2 H2 119.7 . .
C2 C3 C4 119.25(12) . .
C2 C3 H3 120.4 . .
C4 C3 H3 120.4 . .
C5 C4 C3 120.38(11) . .
C5 C4 H4 119.8 . .
C3 C4 H4 119.8 . .
C4 C5 C6 120.70(11) . .
C4 C5 H5 119.7 . .
C6 C5 H5 119.7 . .
C1 C6 C5 118.27(11) . .
C1 C6 C7 119.76(11) . .
C5 C6 C7 121.96(11) . .
N1 C7 C8 106.79(11) . .
N1 C7 C6 122.23(10) . .
C8 C7 C6 130.95(11) . .
C7 C8 C9 107.82(11) . .
C7 C8 H6 126.1 . .
C9 C8 H6 126.1 . .
C10 C9 C8 108.03(11) . .
C10 C9 H7 126.0 . .
C8 C9 H7 126.0 . .
N1 C10 C9 106.42(10) . .
N1 C10 C11 117.12(10) . .
C9 C10 C11 135.63(11) . .
N2 C11 C11 120.03(7) . 4_655
N2 C11 C10 113.76(10) . .
C11 C11 C10 126.12(7) 4_655 .
N2 C12 C13 120.48(11) . .
N2 C12 C12 120.10(7) . 4_655
C13 C12 C12 119.36(7) . 4_655
C14 C13 C12 120.14(12) . .
C14 C13 H8 119.9 . .
C12 C13 H8 119.9 . .
C13 C14 C14 120.43(8) . 4_655
C13 C14 H9 119.8 . .
C14 C14 H9 119.8 4_655 .
C7 N1 C10 110.95(10) . .
C7 N1 H10 124.5 . .
C10 N1 H10 124.5 . .
C11 N2 C12 119.14(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3884(19) .
C1 C6 1.3999(18) .
C1 H1 0.9500 .
C2 C3 1.3887(19) .
C2 H2 0.9500 .
C3 C4 1.3932(18) .
C3 H3 0.9500 .
C4 C5 1.3912(18) .
C4 H4 0.9500 .
C5 C6 1.4024(18) .
C5 H5 0.9500 .
C6 C7 1.4696(17) .
C7 N1 1.3674(16) .
C7 C8 1.3871(17) .
C8 C9 1.4090(18) .
C8 H6 0.9500 .
C9 C10 1.3856(18) .
C9 H7 0.9500 .
C10 N1 1.3785(16) .
C10 C11 1.4616(17) .
C11 N2 1.3276(16) .
C11 C11 1.453(2) 4_655
C12 N2 1.3620(16) .
C12 C13 1.4115(17) .
C12 C12 1.419(2) 4_655
C13 C14 1.3692(18) .
C13 H8 0.9500 .
C14 C14 1.418(3) 4_655
C14 H9 0.9500 .
N1 H10 0.8800 .
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 0.68(18) . .
C1 C2 C3 C4 0.69(18) . .
C2 C3 C4 C5 -1.29(18) . .
C3 C4 C5 C6 0.54(18) . .
C2 C1 C6 C5 -1.42(18) . .
C2 C1 C6 C7 177.20(11) . .
C4 C5 C6 C1 0.81(18) . .
C4 C5 C6 C7 -177.77(11) . .
C1 C6 C7 N1 173.62(11) . .
C5 C6 C7 N1 -7.82(18) . .
C1 C6 C7 C8 -8.6(2) . .
C5 C6 C7 C8 169.93(13) . .
N1 C7 C8 C9 -0.11(14) . .
C6 C7 C8 C9 -178.12(12) . .
C7 C8 C9 C10 0.01(14) . .
C8 C9 C10 N1 0.09(14) . .
C8 C9 C10 C11 -168.62(13) . .
N1 C10 C11 N2 -7.17(16) . .
C9 C10 C11 N2 160.65(14) . .
N1 C10 C11 C11 176.35(13) . 4_655
C9 C10 C11 C11 -15.8(3) . 4_655
N2 C12 C13 C14 -174.11(11) . .
C12 C12 C13 C14 3.2(2) 4_655 .
C12 C13 C14 C14 -0.3(2) . 4_655
C8 C7 N1 C10 0.17(13) . .
C6 C7 N1 C10 178.39(10) . .
C9 C10 N1 C7 -0.16(13) . .
C11 C10 N1 C7 170.99(10) . .
C11 C11 N2 C12 6.9(2) 4_655 .
C10 C11 N2 C12 -169.85(10) . .
C13 C12 N2 C11 -178.62(11) . .
C12 C12 N2 C11 4.10(19) 4_655 .
