#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/31/2233148.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_2233148
loop_
_publ_author_name
'Ge, Yu-Hua'
'Wu, Dong-En'
'Luo, Yang-Hui'
_publ_section_title
;
 3-[(E)-2-Phenylethenyl]-1H-indole-6-carbonitrile
;
_journal_coeditor_code           GG2065
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o207
_journal_paper_doi               10.1107/S1600536811054225
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C17 H12 N2'
_chemical_formula_moiety         'C17 H12 N2'
_chemical_formula_sum            'C17 H12 N2'
_chemical_formula_weight         244.29
_chemical_name_systematic
;
3-[(E)-2-Phenylethenyl]-1H-indole-6-carbonitrile
;
_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                   9.689(8)
_cell_length_b                   7.440(6)
_cell_length_c                   35.53(3)
_cell_measurement_reflns_used    2263
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.15
_cell_volume                     2561(4)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       CCD_Profile_fitting
_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  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            16536
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.15
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 2
_diffrn_standards_interval_time  150
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            Blue
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.197
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2263
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.069P)²+0.3176P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1269
_reflns_number_gt                1867
_reflns_number_total             2263
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg2065.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P b c a '
_cod_database_code               2233148
_cod_database_fobs_code          2233148
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -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 N1 -0.14124(13) 0.36176(18) 0.04780(4) 0.0497(4) Uani d . 1 1
H H1A -0.1933 0.3603 0.0268 0.060 Uiso d R 1 1
N N2 0.17232(16) 1.0338(2) 0.01757(4) 0.0620(4) Uani d . 1 1
C C1 -0.13711(17) 0.2312(2) 0.07463(5) 0.0515(4) Uani d . 1 1
H H1B -0.1876 0.1250 0.0738 0.062 Uiso calc R 1 1
C C2 -0.04867(15) 0.2774(2) 0.10301(4) 0.0437(4) Uani d . 1 1
C C3 0.00642(14) 0.4503(2) 0.09281(4) 0.0388(4) Uani d . 1 1
C C4 0.09969(16) 0.5690(2) 0.10937(4) 0.0448(4) Uani d . 1 1
H H4A 0.1368 0.5438 0.1329 0.054 Uiso calc R 1 1
C C5 -0.01787(14) 0.6535(2) 0.03886(4) 0.0426(4) Uani d . 1 1
H H5A -0.0577 0.6824 0.0158 0.051 Uiso calc R 1 1
C C6 0.07849(15) 0.7645(2) 0.05558(4) 0.0435(4) Uani d . 1 1
C C7 0.13635(17) 0.7231(2) 0.09078(4) 0.0477(4) Uani d . 1 1
H H7A 0.2001 0.8010 0.1016 0.057 Uiso calc R 1 1
C C8 0.12868(16) 0.9173(2) 0.03509(4) 0.0486(4) Uani d . 1 1
C C9 -0.00992(16) 0.1678(2) 0.13506(4) 0.0470(4) Uani d . 1 1
H H9A 0.0605 0.2106 0.1504 0.056 Uiso calc R 1 1
C C10 -0.06676(17) 0.0115(2) 0.14427(5) 0.0508(4) Uani d . 1 1
H H10A -0.1435 -0.0224 0.1302 0.061 Uiso calc R 1 1
C C11 -0.02405(17) -0.1135(2) 0.17358(4) 0.0469(4) Uani d . 1 1
C C12 0.10257(18) -0.1029(2) 0.19183(5) 0.0534(4) Uani d . 1 1
H H12A 0.1627 -0.0094 0.1861 0.064 Uiso calc R 1 1
C C13 0.1402(2) -0.2282(3) 0.21825(5) 0.0649(5) Uani d . 1 1
H H13A 0.2253 -0.2186 0.2302 0.078 Uiso calc R 1 1
C C14 0.0534(2) -0.3680(3) 0.22722(6) 0.0756(6) Uani d . 1 1
H H14A 0.0794 -0.4527 0.2451 0.091 Uiso calc R 1 1
C C15 -0.0719(2) -0.3811(3) 0.20954(6) 0.0795(7) Uani d . 1 1
H H15A -0.1315 -0.4749 0.2155 0.095 Uiso calc R 1 1
C C16 -0.1100(2) -0.2561(3) 0.18295(5) 0.0639(5) Uani d . 1 1
H H16A -0.1949 -0.2673 0.1710 0.077 Uiso calc R 1 1
C C34 -0.05265(14) 0.4975(2) 0.05786(4) 0.0403(4) Uani d . 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
C1 N1 C34 108.91(14)
C1 N1 H1A 126.0
C34 N1 H1A 125.1
N1 C1 C2 110.82(15)
N1 C1 H1B 124.6
C2 C1 H1B 124.6
C1 C2 C3 105.76(14)
C1 C2 C9 126.88(16)
C3 C2 C9 127.18(14)
C34 C3 C4 118.45(14)
C34 C3 C2 107.06(13)
C4 C3 C2 134.49(14)
C7 C4 C3 119.67(15)
C7 C4 H4A 120.2
C3 C4 H4A 120.2
C34 C5 C6 117.15(14)
C34 C5 H5A 121.4
C6 C5 H5A 121.4
C5 C6 C7 121.46(15)
C5 C6 C8 119.00(15)
C7 C6 C8 119.34(15)
C4 C7 C6 120.61(15)
C4 C7 H7A 119.7
C6 C7 H7A 119.7
N2 C8 C6 176.59(18)
C10 C9 C2 125.35(16)
C10 C9 H9A 117.3
C2 C9 H9A 117.3
C9 C10 C11 128.16(16)
C9 C10 H10A 115.9
C11 C10 H10A 115.9
C12 C11 C16 117.45(16)
C12 C11 C10 123.22(15)
C16 C11 C10 119.26(16)
C13 C12 C11 120.99(18)
C13 C12 H12A 119.5
C11 C12 H12A 119.5
C12 C13 C14 120.6(2)
C12 C13 H13A 119.7
C14 C13 H13A 119.7
C15 C14 C13 119.32(19)
C15 C14 H14A 120.3
C13 C14 H14A 120.3
C16 C15 C14 120.3(2)
C16 C15 H15A 119.9
C14 C15 H15A 119.9
C15 C16 C11 121.3(2)
C15 C16 H16A 119.3
C11 C16 H16A 119.3
N1 C34 C5 129.96(14)
N1 C34 C3 107.43(14)
C5 C34 C3 122.59(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.361(2)
N1 C34 1.372(2)
N1 H1A 0.8999
N2 C8 1.148(2)
C1 C2 1.367(2)
C1 H1B 0.9300
C2 C3 1.439(2)
C2 C9 1.450(2)
C3 C34 1.412(2)
C3 C4 1.394(2)
C4 C7 1.370(2)
C4 H4A 0.9300
C5 C34 1.385(2)
C5 C6 1.380(2)
C5 H5A 0.9300
C6 C7 1.405(2)
C6 C8 1.435(2)
C7 H7A 0.9300
C9 C10 1.328(2)
C9 H9A 0.9300
C10 C11 1.457(2)
C10 H10A 0.9300
C11 C12 1.390(3)
C11 C16 1.389(3)
C12 C13 1.373(3)
C12 H12A 0.9300
C13 C14 1.375(3)
C13 H13A 0.9300
C14 C15 1.370(3)
C14 H14A 0.9300
C15 C16 1.376(3)
C15 H15A 0.9300
C16 H16A 0.9300
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 H1A N2 3_465 0.90 2.19 3.043(3) 158
C5 H5A N2 5_575 0.93 2.66 3.416(4) 138
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
C34 N1 C1 C2 0.90(19)
N1 C1 C2 C3 -0.13(18)
N1 C1 C2 C9 -175.44(15)
C1 C2 C3 C34 -0.66(16)
C9 C2 C3 C34 174.63(14)
C1 C2 C3 C4 179.82(17)
C9 C2 C3 C4 -4.9(3)
C34 C3 C4 C7 -3.0(2)
C2 C3 C4 C7 176.51(15)
C34 C5 C6 C7 -1.5(2)
C34 C5 C6 C8 173.32(13)
C3 C4 C7 C6 1.4(2)
C5 C6 C7 C4 0.9(2)
C8 C6 C7 C4 -173.94(15)
C1 C2 C9 C10 -8.2(3)
C3 C2 C9 C10 177.49(15)
C2 C9 C10 C11 173.21(15)
C9 C10 C11 C12 -13.5(3)
C9 C10 C11 C16 169.56(17)
C16 C11 C12 C13 -0.4(2)
C10 C11 C12 C13 -177.41(16)
C11 C12 C13 C14 0.2(3)
C12 C13 C14 C15 -0.1(3)
C13 C14 C15 C16 0.3(3)
C14 C15 C16 C11 -0.6(3)
C12 C11 C16 C15 0.6(3)
C10 C11 C16 C15 177.75(18)
C1 N1 C34 C5 177.01(15)
C1 N1 C34 C3 -1.29(17)
C6 C5 C34 N1 -178.20(15)
C6 C5 C34 C3 -0.1(2)
C4 C3 C34 N1 -179.20(13)
C2 C3 C34 N1 1.20(16)
C4 C3 C34 C5 2.3(2)
C2 C3 C34 C5 -177.26(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657319
