#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/72/2227241.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_2227241
loop_
_publ_author_name
'Velmurugan, R.'
'Sekar, M.'
'Chandramohan, A.'
'Ramesh, P.'
'Ponnuswamy, M. N.'
_publ_section_title
;
 2-(1,2,3,4-Tetrahydro-9H-carbazol-1-ylidene)propanedinitrile
;
_journal_coeditor_code           BT5359
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2965
_journal_paper_doi               10.1107/S1600536810042649
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H11 N3'
_chemical_formula_moiety         'C15 H11 N3'
_chemical_formula_sum            'C15 H11 N3'
_chemical_formula_weight         233.27
_chemical_name_common            1-(Dicyanomethylene)-2,3,4-tetrahydrocarbazole
_chemical_name_systematic
;
2-(1,2,3,4-Tetrahydro-9H-carbazol-1-ylidene)propanedinitrile
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                87.461(8)
_cell_angle_beta                 82.392(8)
_cell_angle_gamma                75.038(7)
_cell_formula_units_Z            2
_cell_length_a                   7.7631(10)
_cell_length_b                   8.0003(10)
_cell_length_c                   9.8933(13)
_cell_measurement_reflns_used    1654
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.37
_cell_measurement_theta_min      2.08
_cell_volume                     588.35(13)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART APEXII area-detector'
_diffrn_measurement_method       'ω and φ 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  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10589
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         2.08
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.153
_refine_ls_extinction_coef       0.038(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2924
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0748P)²+0.0374P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1302
_reflns_number_gt                2339
_reflns_number_total             2924
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5359.cif
_cod_data_source_block           I
_cod_database_code               2227241
_cod_database_fobs_code          2227241
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_disorder_assembly
_atom_site_disorder_group
N N1 0.18203(13) 0.14402(13) 0.01388(9) 0.0404(2) Uani d . 1 . .
H H1 0.118(2) 0.252(2) 0.0038(17) 0.068(4) Uiso d . 1 . .
C C2 0.25866(13) 0.06198(14) 0.12645(10) 0.0375(2) Uani d . 1 . .
C C3 0.26818(13) 0.13570(14) 0.25321(10) 0.0380(3) Uani d . 1 . .
C C4 0.36565(17) 0.01146(17) 0.35406(13) 0.0491(3) Uani d . 1 . .
H H4A 0.3179 0.0527 0.4456 0.059 Uiso calc R 1 . .
H H4B 0.4918 0.0112 0.3398 0.059 Uiso calc R 1 . .
C C5 0.35020(18) -0.17242(16) 0.34360(13) 0.0532(3) Uani d . 1 . .
H H5A 0.2257 -0.1756 0.3670 0.064 Uiso calc R 1 . .
H H5B 0.4204 -0.2461 0.4078 0.064 Uiso calc R 1 . .
C C6 0.41700(17) -0.23982(16) 0.20031(13) 0.0518(3) Uani d . 1 . .
H H6A 0.5464 -0.2582 0.1830 0.062 Uiso calc R 1 . .
H H6B 0.3889 -0.3498 0.1910 0.062 Uiso calc R 1 . .
C C7 0.32980(14) -0.11254(14) 0.09931(11) 0.0412(3) Uani d . 1 . .
C C8 0.29475(14) -0.13856(15) -0.03433(12) 0.0430(3) Uani d . 1 . .
C C9 0.32862(18) -0.28496(18) -0.11570(14) 0.0559(3) Uani d . 1 . .
H H9 0.3900 -0.3926 -0.0849 0.067 Uiso calc R 1 . .
C C10 0.26989(19) -0.2670(2) -0.24143(15) 0.0621(4) Uani d . 1 . .
H H10 0.2916 -0.3636 -0.2963 0.075 Uiso calc R 1 . .
C C11 0.17753(18) -0.1052(2) -0.28854(13) 0.0561(3) Uani d . 1 . .
H H11 0.1390 -0.0972 -0.3743 0.067 Uiso calc R 1 . .
C C12 0.14204(16) 0.04168(17) -0.21264(11) 0.0486(3) Uani d . 1 . .
H H12 0.0815 0.1487 -0.2451 0.058 Uiso calc R 1 . .
C C13 0.20122(14) 0.02303(15) -0.08386(11) 0.0407(3) Uani d . 1 . .
C C14 0.20193(15) 0.30577(15) 0.28668(11) 0.0436(3) Uani d U 1 . .
C C15 0.11508(19) 0.43809(15) 0.19901(13) 0.0519(3) Uani d U 1 . .
N N16 0.0464(2) 0.54705(16) 0.13082(13) 0.0753(4) Uani d . 1 . .
C C17 0.22133(19) 0.36577(18) 0.41741(14) 0.0575(3) Uani d U 1 . .
N N18 0.2367(2) 0.4156(2) 0.51944(15) 0.0918(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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C13 N1 C2 . . 108.44(9) ?
C13 N1 H1 . . 121.1(11) ?
C2 N1 H1 . . 130.1(11) ?
C7 C2 N1 . . 109.30(9) ?
C7 C2 C3 . . 122.29(10) ?
N1 C2 C3 . . 128.42(10) ?
C14 C3 C2 . . 125.47(10) ?
C14 C3 C4 . . 119.15(10) ?
C2 C3 C4 . . 115.36(10) ?
C3 C4 C5 . . 113.84(10) ?
C3 C4 H4A . . 108.8 ?
C5 C4 H4A . . 108.8 ?
C3 C4 H4B . . 108.8 ?
C5 C4 H4B . . 108.8 ?
H4A C4 H4B . . 107.7 ?
C4 C5 C6 . . 110.58(11) ?
C4 C5 H5A . . 109.5 ?
C6 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
C6 C5 H5B . . 109.5 ?
H5A C5 H5B . . 108.1 ?
C7 C6 C5 . . 109.78(10) ?
C7 C6 H6A . . 109.7 ?
C5 C6 H6A . . 109.7 ?
C7 C6 H6B . . 109.7 ?
C5 C6 H6B . . 109.7 ?
H6A C6 H6B . . 108.2 ?
C2 C7 C8 . . 106.56(10) ?
C2 C7 C6 . . 123.35(10) ?
C8 C7 C6 . . 130.04(10) ?
C9 C8 C13 . . 119.21(12) ?
C9 C8 C7 . . 133.37(12) ?
C13 C8 C7 . . 107.37(10) ?
C10 C9 C8 . . 118.88(13) ?
C10 C9 H9 . . 120.6 ?
C8 C9 H9 . . 120.6 ?
C9 C10 C11 . . 120.89(12) ?
C9 C10 H10 . . 119.6 ?
C11 C10 H10 . . 119.6 ?
C12 C11 C10 . . 122.23(12) ?
C12 C11 H11 . . 118.9 ?
C10 C11 H11 . . 118.9 ?
C11 C12 C13 . . 116.83(13) ?
C11 C12 H12 . . 121.6 ?
C13 C12 H12 . . 121.6 ?
N1 C13 C12 . . 129.73(11) ?
N1 C13 C8 . . 108.31(10) ?
C12 C13 C8 . . 121.95(11) ?
C3 C14 C15 . . 125.01(10) ?
C3 C14 C17 . . 120.54(11) ?
C15 C14 C17 . . 114.43(11) ?
N16 C15 C14 . . 178.28(13) ?
N18 C17 C14 . . 178.87(17) ?
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
N1 C13 . 1.3655(14) ?
N1 C2 . 1.3906(14) ?
N1 H1 . 0.885(17) ?
C2 C7 . 1.3865(15) ?
C2 C3 . 1.4278(15) ?
C3 C14 . 1.3634(16) ?
C3 C4 . 1.5098(16) ?
C4 C5 . 1.5156(19) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.5159(18) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 C7 . 1.4921(16) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C8 . 1.4193(16) ?
C8 C9 . 1.3991(16) ?
C8 C13 . 1.4114(17) ?
C9 C10 . 1.370(2) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.401(2) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.3698(18) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.3997(16) ?
C12 H12 . 0.9300 ?
C14 C15 . 1.4257(17) ?
C14 C17 . 1.4386(16) ?
C15 N16 . 1.1413(17) ?
C17 N18 . 1.1334(17) ?
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
N1 H1 N16 1 0.885(17) 2.623(17) 3.3314(16) 137.8(13)
N1 H1 N16 2_565 0.885(17) 2.279(17) 3.0656(17) 148.1(14)
C12 H12 N16 2_565 0.93 2.62 3.3254(19) 132.6
C4 H4B Cg3 2_655 0.97 2.86 3.6950(15) 145
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C13 N1 C2 C7 . . . . 0.92(12) ?
C13 N1 C2 C3 . . . . -179.03(10) ?
C7 C2 C3 C14 . . . . 179.75(10) ?
N1 C2 C3 C14 . . . . -0.31(19) ?
C7 C2 C3 C4 . . . . 1.66(15) ?
N1 C2 C3 C4 . . . . -178.40(10) ?
C14 C3 C4 C5 . . . . 150.75(11) ?
C2 C3 C4 C5 . . . . -31.03(14) ?
C3 C4 C5 C6 . . . . 56.40(14) ?
C4 C5 C6 C7 . . . . -50.35(13) ?
N1 C2 C7 C8 . . . . -0.30(12) ?
C3 C2 C7 C8 . . . . 179.65(9) ?
N1 C2 C7 C6 . . . . -177.95(10) ?
C3 C2 C7 C6 . . . . 2.00(17) ?
C5 C6 C7 C2 . . . . 23.15(15) ?
C5 C6 C7 C8 . . . . -153.90(12) ?
C2 C7 C8 C9 . . . . -177.95(12) ?
C6 C7 C8 C9 . . . . -0.5(2) ?
C2 C7 C8 C13 . . . . -0.40(12) ?
C6 C7 C8 C13 . . . . 177.03(11) ?
C13 C8 C9 C10 . . . . 0.02(18) ?
C7 C8 C9 C10 . . . . 177.34(12) ?
C8 C9 C10 C11 . . . . 0.1(2) ?
C9 C10 C11 C12 . . . . 0.2(2) ?
C10 C11 C12 C13 . . . . -0.53(18) ?
C2 N1 C13 C12 . . . . 178.09(11) ?
C2 N1 C13 C8 . . . . -1.16(12) ?
C11 C12 C13 N1 . . . . -178.53(11) ?
C11 C12 C13 C8 . . . . 0.64(17) ?
C9 C8 C13 N1 . . . . 178.93(10) ?
C7 C8 C13 N1 . . . . 0.97(12) ?
C9 C8 C13 C12 . . . . -0.40(17) ?
C7 C8 C13 C12 . . . . -178.35(10) ?
C2 C3 C14 C15 . . . . -1.19(19) ?
C4 C3 C14 C15 . . . . 176.84(11) ?
C2 C3 C14 C17 . . . . -179.26(11) ?
C4 C3 C14 C17 . . . . -1.23(17) ?
C3 C14 C15 N16 . . . . -161(5) ?
C17 C14 C15 N16 . . . . 17(5) ?
C3 C14 C17 N18 . . . . 149(9) ?
C15 C14 C17 N18 . . . . -30(9) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745316
