#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:17:15 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178464 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/85/4028551.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_4028551
loop_
_publ_author_name
'Styliana I. Mirallai'
'Maria Manoli'
'Panayiotis A. Koutentis'
_publ_section_title
;
 Reactions of Tetracyanoethylene with N'-Arylbenzamidines: A Route to
 2-Phenyl-3H-imidazo[4,5-b]quinoline-9-carbonitriles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8655
_journal_page_last               8668
_journal_paper_doi               10.1021/jo4013699
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C18 H11 N5'
_chemical_formula_sum            'C18 H11 N5'
_chemical_formula_weight         297.32
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   6.7212(5)
_cell_length_b                   16.922(2)
_cell_length_c                   25.652(3)
_cell_measurement_reflns_used    1993
_cell_measurement_temperature    100.3(4)
_cell_measurement_theta_max      67.3496
_cell_measurement_theta_min      3.1260
_cell_volume                     2917.6(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4223
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) x-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6039
_diffrn_reflns_theta_full        66.97
_diffrn_reflns_theta_max         66.97
_diffrn_reflns_theta_min         3.45
_exptl_absorpt_coefficient_mu    0.683
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71367
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'empirical absorption correction (CrysAlis RED, Oxford Diffraction)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       rod
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.0006(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0541
_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)+(0.1166P)²+0.0949P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1582
_refine_ls_wR_factor_ref         0.1703
_reflns_number_gt                2161
_reflns_number_total             2584
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4013699_si_002.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        2917.5(5)
_cod_original_sg_symbol_H-M      ' P b c a'
_cod_database_code               4028551
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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 0.0620(2) 0.30107(11) 0.35411(7) 0.0254(4) Uani 1 1 d .
C2 C 0.0533(3) 0.31803(11) 0.41007(7) 0.0261(4) Uani 1 1 d .
C3 C -0.0753(3) 0.37775(11) 0.42747(8) 0.0282(4) Uani 1 1 d .
H3 H -0.1559 0.4044 0.4038 0.034 Uiso 1 1 calc R
C4 C -0.0819(3) 0.39693(12) 0.47996(8) 0.0299(4) Uani 1 1 d .
H4 H -0.1682 0.4361 0.4915 0.036 Uiso 1 1 calc R
C5 C 0.0400(3) 0.35783(12) 0.51540(8) 0.0307(5) Uani 1 1 d .
H5 H 0.0347 0.3708 0.5506 0.037 Uiso 1 1 calc R
C6 C 0.1690(3) 0.29971(12) 0.49828(8) 0.0311(5) Uani 1 1 d .
H6 H 0.2517 0.2743 0.5220 0.037 Uiso 1 1 calc R
C7 C 0.1759(3) 0.27904(11) 0.44579(7) 0.0285(4) Uani 1 1 d .
H7 H 0.2618 0.2395 0.4345 0.034 Uiso 1 1 calc R
C8 C 0.1069(3) 0.15235(11) 0.35908(7) 0.0278(4) Uani 1 1 d .
C9 C -0.0556(3) 0.12513(12) 0.38722(8) 0.0321(5) Uani 1 1 d .
H9 H -0.1709 0.1552 0.3898 0.039 Uiso 1 1 calc R
C10 C -0.0418(3) 0.05172(13) 0.41146(8) 0.0370(5) Uani 1 1 d .
H10 H -0.1471 0.0334 0.4317 0.044 Uiso 1 1 calc R
C11 C 0.1275(4) 0.00566(12) 0.40573(8) 0.0382(5) Uani 1 1 d .
H11 H 0.1351 -0.0435 0.4218 0.046 Uiso 1 1 calc R
C12 C 0.2852(3) 0.03296(12) 0.37602(8) 0.0348(5) Uani 1 1 d .
H12 H 0.3969 0.0013 0.3713 0.042 Uiso 1 1 calc R
C13 C 0.2771(3) 0.10763(11) 0.35321(7) 0.0297(4) Uani 1 1 d .
H13 H 0.3847 0.1270 0.3343 0.036 Uiso 1 1 calc R
C14 C 0.0929(2) 0.23546(11) 0.27841(7) 0.0255(4) Uani 1 1 d .
C15 C 0.0591(2) 0.32165(11) 0.27135(7) 0.0252(4) Uani 1 1 d .
C16 C 0.0512(3) 0.36126(12) 0.22475(7) 0.0275(5) Uani 1 1 d .
C17 C 0.0354(3) 0.44586(12) 0.22556(7) 0.0324(5) Uani 1 1 d .
C18 C 0.0610(3) 0.32188(12) 0.17537(8) 0.0283(5) Uani 1 1 d .
N1 N 0.0951(2) 0.22762(9) 0.33353(6) 0.0259(4) Uani 1 1 d .
N2 N 0.0398(2) 0.35786(10) 0.31874(6) 0.0268(4) Uani 1 1 d .
N3 N 0.1138(3) 0.18383(10) 0.24312(7) 0.0317(4) Uani 1 1 d .
H14A H 0.133(8) 0.130(3) 0.255(2) 0.038 Uiso 0.50 1 d P
H14B H 0.149(8) 0.191(3) 0.218(2) 0.038 Uiso 0.50 1 d P
N4 N 0.0652(2) 0.29138(11) 0.13536(7) 0.0343(4) Uani 1 1 d .
N5 N 0.0263(3) 0.51329(12) 0.22810(8) 0.0468(5) 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
N2 C1 N1 114.29(17)
N2 C1 C2 121.49(17)
N1 C1 C2 124.22(17)
C7 C2 C3 119.66(18)
C7 C2 C1 121.74(17)
C3 C2 C1 118.53(17)
C4 C3 C2 119.85(18)
C4 C3 H3 120.1
C2 C3 H3 120.1
C3 C4 C5 120.31(18)
C3 C4 H4 119.8
C5 C4 H4 119.8
C6 C5 C4 120.00(18)
C6 C5 H5 120.0
C4 C5 H5 120.0
C5 C6 C7 120.46(18)
C5 C6 H6 119.8
C7 C6 H6 119.8
C6 C7 C2 119.71(18)
C6 C7 H7 120.1
C2 C7 H7 120.1
C13 C8 C9 121.82(18)
C13 C8 N1 118.87(16)
C9 C8 N1 119.26(17)
C8 C9 C10 118.44(18)
C8 C9 H9 120.8
C10 C9 H9 120.8
C11 C10 C9 120.57(19)
C11 C10 H10 119.7
C9 C10 H10 119.7
C12 C11 C10 119.92(19)
C12 C11 H11 120.0
C10 C11 H11 120.0
C11 C12 C13 120.26(19)
C11 C12 H12 119.9
C13 C12 H12 119.9
C8 C13 C12 118.91(18)
C8 C13 H13 120.5
C12 C13 H13 120.5
N3 C14 N1 130.26(18)
N3 C14 C15 127.36(17)
N1 C14 C15 102.38(15)
N2 C15 C16 123.51(18)
N2 C15 C14 110.23(15)
C16 C15 C14 126.25(17)
C15 C16 C18 122.78(18)
C15 C16 C17 118.53(17)
C18 C16 C17 118.68(17)
N5 C17 C16 177.3(2)
N4 C18 C16 178.4(2)
C1 N1 C14 107.31(15)
C1 N1 C8 129.72(16)
C14 N1 C8 122.57(15)
C1 N2 C15 105.77(16)
C14 N3 H14A 116(3)
C14 N3 H14B 126(4)
H14A N3 H14B 114(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.330(3)
C1 N1 1.368(2)
C1 C2 1.465(3)
C2 C7 1.398(3)
C2 C3 1.402(3)
C3 C4 1.386(3)
C3 H3 0.9300
C4 C5 1.391(3)
C4 H4 0.9300
C5 C6 1.383(3)
C5 H5 0.9300
C6 C7 1.392(3)
C6 H6 0.9300
C7 H7 0.9300
C8 C13 1.380(3)
C8 C9 1.388(3)
C8 N1 1.435(2)
C9 C10 1.392(3)
C9 H9 0.9300
C10 C11 1.387(3)
C10 H10 0.9300
C11 C12 1.385(3)
C11 H11 0.9300
C12 C13 1.393(3)
C12 H12 0.9300
C13 H13 0.9300
C14 N3 1.266(3)
C14 N1 1.420(2)
C14 C15 1.487(3)
C15 N2 1.368(2)
C15 C16 1.372(3)
C16 C18 1.433(3)
C16 C17 1.436(3)
C17 N5 1.145(3)
C18 N4 1.149(3)
N3 H14A 0.98(6)
N3 H14B 0.70(6)
