#------------------------------------------------------------------------------
#$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176809 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/01/2240193.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_2240193
loop_
_publ_author_name
'Mague, Joel T.'
'Mohamed, Shaaban K.'
'Akkurt, Mehmet'
'El-Kashef, Hussein M. S.'
'Albayati, Mustafa R.'
_publ_section_title
;
 Crystal structure of
 2-[12-methyl-14-phenyl-10,13,14,16-tetraazatetracyclo[7.7.0.0^2,7^.0^11,15^]hexadeca-1(16),2,4,6,9,11(15),12-heptaen-8-ylidene]propandinitrile
;
_journal_coeditor_code           SU5012
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1244
_journal_page_last               o1245
_journal_paper_doi               10.1107/S1600536814024167
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C22 H12 N6'
_chemical_formula_moiety         'C22 H12 N6'
_chemical_formula_sum            'C22 H12 N6'
_chemical_formula_weight         360.38
_chemical_name_systematic
2-{12-Methyl-14-phenyl-10,13,14,16-tetraazatetracyclo[7.7.0.0^2,7^.0^11,15^]hexadeca-1(16),2,4,6,9,11(15),12-heptaen-8-ylidene}propandinitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 129.6130(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   35.968(5)
_cell_length_b                   4.6483(6)
_cell_length_c                   26.596(3)
_cell_measurement_reflns_used    4540
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.4298
_cell_measurement_theta_min      2.2678
_cell_volume                     3425.5(8)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2008)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.3660
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            15751
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         27.522
_diffrn_reflns_theta_min         1.988
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.198
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3921
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0534
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0537P)²+1.9123P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1364
_reflns_number_gt                2489
_reflns_number_total             3921
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su5012sup1.cif
_cod_data_source_block           I
_cod_database_code               2240193
_cod_database_fobs_code          2240193
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.994
_shelxl_version_number           2.014
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.69392(6) 0.2255(4) 0.36211(8) 0.0427(4) Uani d 1 . .
N N2 0.66369(7) 0.0716(4) 0.36798(9) 0.0482(5) Uani d 1 . .
N N3 0.68329(6) 0.5915(3) 0.28798(8) 0.0385(4) Uani d 1 . .
N N4 0.58234(6) 0.5174(4) 0.23053(8) 0.0418(4) Uani d 1 . .
N N5 0.46527(7) 0.6261(5) 0.12918(10) 0.0679(6) Uani d 1 . .
N N6 0.46809(7) 1.2638(5) 0.01592(10) 0.0657(6) Uani d 1 . .
C C1 0.74396(18) 0.1886(11) 0.4101(2) 0.0444(5) Uani d 0.516(4) A 1
C C2 0.7750(3) 0.2928(12) 0.4002(2) 0.0565(14) Uani d 0.516(4) A 1
H H2 0.7624 0.3876 0.3605 0.068 Uiso calc 0.516(4) A 1
C C3 0.8246(2) 0.2582(13) 0.4482(3) 0.0568(13) Uani d 0.516(4) A 1
H H3 0.8458 0.3294 0.4414 0.068 Uiso calc 0.516(4) A 1
C C4 0.84309(16) 0.1195(12) 0.5063(3) 0.0611(7) Uani d 0.516(4) A 1
H H4 0.8770 0.0959 0.5391 0.073 Uiso calc 0.516(4) A 1
C C5 0.81201(19) 0.0153(11) 0.5163(2) 0.0596(12) Uani d 0.516(4) A 1
H H5 0.8246 -0.0795 0.5559 0.072 Uiso calc 0.516(4) A 1
C C6 0.76244(18) 0.0498(11) 0.4682(2) 0.0551(11) Uani d 0.516(4) A 1
H H6 0.7412 -0.0214 0.4750 0.066 Uiso calc 0.516(4) A 1
C C1A 0.74487(19) 0.1788(12) 0.4091(2) 0.0444(5) Uani d 0.484(4) A 2
C C2A 0.7774(3) 0.3742(10) 0.4168(3) 0.0565(14) Uani d 0.484(4) A 2
H H2A 0.7660 0.5350 0.3884 0.068 Uiso calc 0.484(4) A 2
C C3A 0.8267(3) 0.3344(11) 0.4661(4) 0.0568(13) Uani d 0.484(4) A 2
H H3A 0.8490 0.4679 0.4714 0.068 Uiso calc 0.484(4) A 2
C C4A 0.84344(17) 0.0991(13) 0.5077(3) 0.0611(7) Uani d 0.484(4) A 2
H H4A 0.8771 0.0719 0.5414 0.073 Uiso calc 0.484(4) A 2
C C5A 0.8109(2) -0.0963(11) 0.5000(2) 0.0596(12) Uani d 0.484(4) A 2
H H5A 0.8223 -0.2571 0.5284 0.072 Uiso calc 0.484(4) A 2
C C6A 0.76159(19) -0.0564(11) 0.4507(3) 0.0551(11) Uani d 0.484(4) A 2
H H6A 0.7393 -0.1900 0.4454 0.066 Uiso calc 0.484(4) A 2
C C7 0.66759(7) 0.4096(4) 0.31061(9) 0.0385(5) Uani d 1 . .
C C8 0.61906(7) 0.3724(4) 0.28314(10) 0.0395(5) Uani d 1 . .
C C9 0.61930(8) 0.1579(4) 0.32169(11) 0.0458(5) Uani d 1 . .
C C10 0.57752(8) 0.0445(5) 0.31473(12) 0.0575(6) Uani d 1 . .
H H10A 0.5884 -0.1118 0.3461 0.086 Uiso calc 1 . .
H H10B 0.5530 -0.0286 0.2703 0.086 Uiso calc 1 . .
H H10C 0.5636 0.1991 0.3232 0.086 Uiso calc 1 . .
C C11 0.64643(7) 0.7328(4) 0.23600(9) 0.0360(4) Uani d 1 . .
C C12 0.64814(7) 0.9456(4) 0.19683(9) 0.0368(4) Uani d 1 . .
C C13 0.68659(7) 1.0487(4) 0.20208(10) 0.0424(5) Uani d 1 . .
H H13 0.7185 0.9834 0.2359 0.051 Uiso calc 1 . .
C C14 0.67732(8) 1.2503(5) 0.15671(10) 0.0470(5) Uani d 1 . .
H H14 0.7032 1.3228 0.1594 0.056 Uiso calc 1 . .
C C15 0.63093(8) 1.3466(5) 0.10772(10) 0.0480(5) Uani d 1 . .
H H15 0.6255 1.4850 0.0774 0.058 Uiso calc 1 . .
C C16 0.59220(7) 1.2445(4) 0.10213(10) 0.0440(5) Uani d 1 . .
H H16 0.5604 1.3125 0.0684 0.053 Uiso calc 1 . .
C C17 0.60064(7) 1.0419(4) 0.14650(9) 0.0387(5) Uani d 1 . .
C C18 0.56731(7) 0.8908(4) 0.15189(9) 0.0389(5) Uani d 1 . .
C C19 0.59741(7) 0.6983(4) 0.20825(9) 0.0379(4) Uani d 1 . .
C C20 0.51870(7) 0.9165(4) 0.11397(10) 0.0421(5) Uani d 1 . .
C C21 0.49030(8) 0.7526(5) 0.12444(11) 0.0499(5) Uani d 1 . .
C C22 0.49111(8) 1.1104(5) 0.05965(11) 0.0491(5) Uani d 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
C7 N1 N2 110.14(16)
C7 N1 C1 131.2(3)
N2 N1 C1 118.4(3)
C7 N1 C1A 131.0(3)
N2 N1 C1A 118.8(3)
C9 N2 N1 107.95(16)
C11 N3 C7 110.46(16)
C19 N4 C8 111.93(16)
C2 C1 C6 120.0
C2 C1 N1 120.3(4)
C6 C1 N1 119.7(4)
C3 C2 C1 120.0
C3 C2 H2 120.0
C1 C2 H2 120.0
C2 C3 C4 120.0
C2 C3 H3 120.0
C4 C3 H3 120.0
C5 C4 C3 120.0
C5 C4 H4 120.0
C3 C4 H4 120.0
C6 C5 C4 120.0
C6 C5 H5 120.0
C4 C5 H5 120.0
C5 C6 C1 120.0
C5 C6 H6 120.0
C1 C6 H6 120.0
C2A C1A C6A 120.0
C2A C1A N1 121.3(4)
C6A C1A N1 118.5(4)
C1A C2A C3A 120.0
C1A C2A H2A 120.0
C3A C2A H2A 120.0
C4A C3A C2A 120.0
C4A C3A H3A 120.0
C2A C3A H3A 120.0
C5A C4A C3A 120.0
C5A C4A H4A 120.0
C3A C4A H4A 120.0
C4A C5A C6A 120.0
C4A C5A H5A 120.0
C6A C5A H5A 120.0
C5A C6A C1A 120.0
C5A C6A H6A 120.0
C1A C6A H6A 120.0
N3 C7 N1 128.40(18)
N3 C7 C8 125.22(18)
N1 C7 C8 106.37(17)
N4 C8 C7 123.33(18)
N4 C8 C9 130.67(19)
C7 C8 C9 105.99(18)
N2 C9 C8 109.54(18)
N2 C9 C10 122.5(2)
C8 C9 C10 128.0(2)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
N3 C11 C19 124.72(17)
N3 C11 C12 127.38(17)
C19 C11 C12 107.90(16)
C13 C12 C17 120.84(18)
C13 C12 C11 130.85(18)
C17 C12 C11 108.30(16)
C12 C13 C14 118.35(19)
C12 C13 H13 120.8
C14 C13 H13 120.8
C15 C14 C13 120.9(2)
C15 C14 H14 119.5
C13 C14 H14 119.5
C14 C15 C16 121.1(2)
C14 C15 H15 119.4
C16 C15 H15 119.4
C17 C16 C15 118.82(19)
C17 C16 H16 120.6
C15 C16 H16 120.6
C16 C17 C12 119.95(18)
C16 C17 C18 131.13(18)
C12 C17 C18 108.91(17)
C20 C18 C19 125.14(18)
C20 C18 C17 128.95(19)
C19 C18 C17 105.91(16)
N4 C19 C11 124.33(18)
N4 C19 C18 126.69(17)
C11 C19 C18 108.98(17)
C18 C20 C22 122.7(2)
C18 C20 C21 123.22(19)
C22 C20 C21 114.06(18)
N5 C21 C20 176.0(2)
N6 C22 C20 178.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C7 1.361(2)
N1 N2 1.391(2)
N1 C1 1.403(5)
N1 C1A 1.430(5)
N2 C9 1.311(3)
N3 C11 1.328(2)
N3 C7 1.353(2)
N4 C19 1.327(2)
N4 C8 1.342(3)
N5 C21 1.147(3)
N6 C22 1.148(3)
C1 C2 1.3900
C1 C6 1.3900
C2 C3 1.3900
C2 H2 0.9500
C3 C4 1.3900
C3 H3 0.9500
C4 C5 1.3900
C4 H4 0.9500
C5 C6 1.3900
C5 H5 0.9500
C6 H6 0.9500
C1A C2A 1.3900
C1A C6A 1.3900
C2A C3A 1.3900
C2A H2A 0.9500
C3A C4A 1.3900
C3A H3A 0.9500
C4A C5A 1.3900
C4A H4A 0.9500
C5A C6A 1.3900
C5A H5A 0.9500
C6A H6A 0.9500
C7 C8 1.409(3)
C8 C9 1.426(3)
C9 C10 1.489(3)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 C19 1.421(3)
C11 C12 1.466(3)
C12 C13 1.384(3)
C12 C17 1.413(3)
C13 C14 1.390(3)
C13 H13 0.9500
C14 C15 1.382(3)
C14 H14 0.9500
C15 C16 1.387(3)
C15 H15 0.9500
C16 C17 1.384(3)
C16 H16 0.9500
C17 C18 1.474(3)
C18 C20 1.356(3)
C18 C19 1.466(3)
C20 C22 1.434(3)
C20 C21 1.437(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C10 H10A N5 2_645 0.98 2.69 3.362(3) 126 yes
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
C7 N1 N2 C9 -0.6(2)
C1 N1 N2 C9 174.4(2)
C1A N1 N2 C9 177.4(3)
C7 N1 C1 C2 -18.7(4)
N2 N1 C1 C2 167.6(2)
C1A N1 C1 C2 69(11)
C7 N1 C1 C6 160.6(3)
N2 N1 C1 C6 -13.1(4)
C1A N1 C1 C6 -112(11)
C6 C1 C2 C3 0.0
N1 C1 C2 C3 179.3(4)
C1 C2 C3 C4 0.0
C2 C3 C4 C5 0.0
C3 C4 C5 C6 0.0
C4 C5 C6 C1 0.0
C2 C1 C6 C5 0.0
N1 C1 C6 C5 -179.3(4)
C7 N1 C1A C2A 14.8(4)
N2 N1 C1A C2A -162.6(3)
C1 N1 C1A C2A -80(11)
C7 N1 C1A C6A -169.9(3)
N2 N1 C1A C6A 12.7(4)
C1 N1 C1A C6A 95(11)
C6A C1A C2A C3A 0.0
N1 C1A C2A C3A 175.2(4)
C1A C2A C3A C4A 0.0
C2A C3A C4A C5A 0.0
C3A C4A C5A C6A 0.0
C4A C5A C6A C1A 0.0
C2A C1A C6A C5A 0.0
N1 C1A C6A C5A -175.3(4)
C11 N3 C7 N1 179.02(18)
C11 N3 C7 C8 0.3(3)
N2 N1 C7 N3 -178.56(18)
C1 N1 C7 N3 7.3(4)
C1A N1 C7 N3 3.8(4)
N2 N1 C7 C8 0.4(2)
C1 N1 C7 C8 -173.8(3)
C1A N1 C7 C8 -177.2(3)
C19 N4 C8 C7 -0.3(3)
C19 N4 C8 C9 -179.28(19)
N3 C7 C8 N4 -0.3(3)
N1 C7 C8 N4 -179.24(17)
N3 C7 C8 C9 178.93(17)
N1 C7 C8 C9 0.0(2)
N1 N2 C9 C8 0.6(2)
N1 N2 C9 C10 -177.98(18)
N4 C8 C9 N2 178.80(19)
C7 C8 C9 N2 -0.3(2)
N4 C8 C9 C10 -2.8(4)
C7 C8 C9 C10 178.1(2)
C7 N3 C11 C19 0.2(3)
C7 N3 C11 C12 -179.09(17)
N3 C11 C12 C13 1.4(3)
C19 C11 C12 C13 -177.97(19)
N3 C11 C12 C17 -179.69(18)
C19 C11 C12 C17 0.9(2)
C17 C12 C13 C14 0.2(3)
C11 C12 C13 C14 178.95(19)
C12 C13 C14 C15 0.3(3)
C13 C14 C15 C16 -0.3(3)
C14 C15 C16 C17 -0.3(3)
C15 C16 C17 C12 0.8(3)
C15 C16 C17 C18 -178.22(19)
C13 C12 C17 C16 -0.8(3)
C11 C12 C17 C16 -179.76(17)
C13 C12 C17 C18 178.45(17)
C11 C12 C17 C18 -0.6(2)
C16 C17 C18 C20 -0.9(3)
C12 C17 C18 C20 179.99(19)
C16 C17 C18 C19 179.1(2)
C12 C17 C18 C19 0.0(2)
C8 N4 C19 C11 0.8(3)
C8 N4 C19 C18 -179.82(17)
N3 C11 C19 N4 -0.8(3)
C12 C11 C19 N4 178.58(17)
N3 C11 C19 C18 179.68(17)
C12 C11 C19 C18 -0.9(2)
C20 C18 C19 N4 1.1(3)
C17 C18 C19 N4 -178.91(18)
C20 C18 C19 C11 -179.43(18)
C17 C18 C19 C11 0.6(2)
C19 C18 C20 C22 179.49(18)
C17 C18 C20 C22 -0.5(3)
C19 C18 C20 C21 -0.6(3)
C17 C18 C20 C21 179.43(18)
