#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/46/2224655.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_2224655
loop_
_publ_author_name
'Li, Jiang-Sheng'
'He, Qi-Xi'
'Li, Peng-Yu'
_publ_section_title
;
 2-Methyl-3-p-tolyl-3H-benzo[e]indole-1-carbonitrile
;
_journal_coeditor_code           HB5275
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o111
_journal_paper_doi               10.1107/S1600536809052441
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H16 N2'
_chemical_formula_moiety         'C21 H16 N2'
_chemical_formula_sum            'C21 H16 N2'
_chemical_formula_weight         296.36
_chemical_name_systematic
;
2-Methyl-3-p-tolyl-3H-benzo[e]indole-1-carbonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 107.14(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.321(2)
_cell_length_b                   12.422(3)
_cell_length_c                   13.258(3)
_cell_measurement_reflns_used    3474
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.495
_cell_measurement_theta_min      2.212
_cell_volume                     1624.3(7)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_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 7.31
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10714
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.21
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.162
_refine_ls_extinction_coef       0.070(10)
_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   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2858
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0564
_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)+(0.1027P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1492
_refine_ls_wR_factor_ref         0.1676
_reflns_number_gt                2092
_reflns_number_total             2858
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5275.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1624.4(6)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2224655
_cod_database_fobs_code          2224655
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.10089(15) 0.87702(12) 0.23973(11) 0.0575(5) Uani d . 1 . .
N N2 -0.2675(2) 1.06928(18) 0.01735(16) 0.1025(8) Uani d . 1 . .
C C1 0.00439(18) 0.79674(14) 0.23281(13) 0.0547(5) Uani d . 1 . .
C C2 0.0217(2) 0.69469(15) 0.27979(14) 0.0629(5) Uani d . 1 . .
H H2 0.1053 0.6728 0.3241 0.075 Uiso calc R 1 . .
C C3 -0.0883(2) 0.62878(16) 0.25826(15) 0.0679(6) Uani d . 1 . .
H H3 -0.0790 0.5606 0.2885 0.081 Uiso calc R 1 . .
C C4 -0.2171(2) 0.66084(17) 0.19091(15) 0.0631(6) Uani d . 1 . .
C C5 -0.3298(2) 0.5901(2) 0.16630(16) 0.0806(7) Uani d . 1 . .
H H5 -0.3197 0.5211 0.1947 0.097 Uiso calc R 1 . .
C C6 -0.4540(2) 0.6220(2) 0.10095(19) 0.0900(8) Uani d . 1 . .
H H6 -0.5266 0.5742 0.0854 0.108 Uiso calc R 1 . .
C C7 -0.4715(2) 0.7253(2) 0.05799(18) 0.0860(7) Uani d . 1 . .
H H7 -0.5561 0.7467 0.0150 0.103 Uiso calc R 1 . .
C C8 -0.3656(2) 0.79452(19) 0.07884(15) 0.0692(6) Uani d . 1 . .
H H8 -0.3783 0.8630 0.0491 0.083 Uiso calc R 1 . .
C C9 -0.23647(19) 0.76498(16) 0.14464(13) 0.0580(5) Uani d . 1 . .
C C10 -0.12000(19) 0.83318(14) 0.16682(12) 0.0542(5) Uani d . 1 . .
C C11 -0.0941(2) 0.93897(14) 0.13370(13) 0.0589(5) Uani d . 1 . .
C C12 0.0402(2) 0.96343(15) 0.17945(14) 0.0608(5) Uani d . 1 . .
C C13 0.1146(3) 1.06418(17) 0.17368(17) 0.0812(7) Uani d . 1 . .
H H13A 0.1546 1.0918 0.2436 0.122 Uiso calc R 1 . .
H H13B 0.0529 1.1164 0.1323 0.122 Uiso calc R 1 . .
H H13C 0.1847 1.0496 0.1414 0.122 Uiso calc R 1 . .
C C14 -0.1898(2) 1.01126(18) 0.06895(15) 0.0722(6) Uani d . 1 . .
C C15 0.24140(19) 0.86902(14) 0.29878(14) 0.0556(5) Uani d . 1 . .
C C16 0.3392(2) 0.85881(17) 0.24716(15) 0.0670(6) Uani d . 1 . .
H H16 0.3146 0.8569 0.1738 0.080 Uiso calc R 1 . .
C C17 0.4734(2) 0.85143(16) 0.30554(17) 0.0722(6) Uani d . 1 . .
H H17 0.5388 0.8442 0.2704 0.087 Uiso calc R 1 . .
C C18 0.5142(2) 0.85442(15) 0.41425(17) 0.0670(6) Uani d . 1 . .
C C19 0.4147(2) 0.86356(17) 0.46373(16) 0.0717(6) Uani d . 1 . .
H H19 0.4395 0.8647 0.5371 0.086 Uiso calc R 1 . .
C C20 0.2793(2) 0.87108(16) 0.40767(14) 0.0661(6) Uani d . 1 . .
H H20 0.2140 0.8775 0.4430 0.079 Uiso calc R 1 . .
C C21 0.6620(2) 0.8465(2) 0.4766(2) 0.1000(9) Uani d . 1 . .
H H21A 0.6952 0.7759 0.4682 0.150 Uiso d R 1 . .
H H21B 0.6720 0.8594 0.5499 0.150 Uiso d R 1 . .
H H21C 0.7128 0.8993 0.4513 0.150 Uiso d R 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
C12 N1 C1 . . 109.04(15) ?
C12 N1 C15 . . 125.88(15) ?
C1 N1 C15 . . 125.07(14) ?
N1 C1 C10 . . 108.42(15) ?
N1 C1 C2 . . 128.59(17) ?
C10 C1 C2 . . 122.97(17) ?
C3 C2 C1 . . 117.55(18) ?
C3 C2 H2 . . 121.2 ?
C1 C2 H2 . . 121.2 ?
C2 C3 C4 . . 122.07(18) ?
C2 C3 H3 . . 119.0 ?
C4 C3 H3 . . 119.0 ?
C5 C4 C9 . . 117.6(2) ?
C5 C4 C3 . . 121.5(2) ?
C9 C4 C3 . . 120.85(18) ?
C6 C5 C4 . . 121.0(2) ?
C6 C5 H5 . . 119.5 ?
C4 C5 H5 . . 119.5 ?
C5 C6 C7 . . 120.4(2) ?
C5 C6 H6 . . 119.8 ?
C7 C6 H6 . . 119.8 ?
C8 C7 C6 . . 120.1(2) ?
C8 C7 H7 . . 120.0 ?
C6 C7 H7 . . 120.0 ?
C7 C8 C9 . . 121.4(2) ?
C7 C8 H8 . . 119.3 ?
C9 C8 H8 . . 119.3 ?
C8 C9 C4 . . 119.45(19) ?
C8 C9 C10 . . 123.90(19) ?
C4 C9 C10 . . 116.63(17) ?
C1 C10 C9 . . 119.89(17) ?
C1 C10 C11 . . 105.56(17) ?
C9 C10 C11 . . 134.53(16) ?
C12 C11 C14 . . 123.93(19) ?
C12 C11 C10 . . 108.80(15) ?
C14 C11 C10 . . 127.20(19) ?
C11 C12 N1 . . 108.18(17) ?
C11 C12 C13 . . 129.44(18) ?
N1 C12 C13 . . 122.34(18) ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
N2 C14 C11 . . 179.4(3) ?
C20 C15 C16 . . 119.78(18) ?
C20 C15 N1 . . 119.91(18) ?
C16 C15 N1 . . 120.31(16) ?
C17 C16 C15 . . 119.24(17) ?
C17 C16 H16 . . 120.4 ?
C15 C16 H16 . . 120.4 ?
C16 C17 C18 . . 122.2(2) ?
C16 C17 H17 . . 118.9 ?
C18 C17 H17 . . 118.9 ?
C19 C18 C17 . . 117.41(19) ?
C19 C18 C21 . . 121.3(2) ?
C17 C18 C21 . . 121.2(2) ?
C18 C19 C20 . . 121.91(19) ?
C18 C19 H19 . . 119.0 ?
C20 C19 H19 . . 119.0 ?
C19 C20 C15 . . 119.5(2) ?
C19 C20 H20 . . 120.3 ?
C15 C20 H20 . . 120.3 ?
C18 C21 H21A . . 109.5 ?
C18 C21 H21B . . 109.4 ?
H21A C21 H21B . . 109.5 ?
C18 C21 H21C . . 109.4 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
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 C12 . 1.374(2) ?
N1 C1 . 1.393(2) ?
N1 C15 . 1.434(2) ?
N2 C14 . 1.143(2) ?
C1 C10 . 1.399(2) ?
C1 C2 . 1.400(2) ?
C2 C3 . 1.360(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.422(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.417(3) ?
C4 C9 . 1.420(3) ?
C5 C6 . 1.377(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.394(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.354(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.409(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.429(3) ?
C10 C11 . 1.435(3) ?
C11 C12 . 1.373(3) ?
C11 C14 . 1.421(3) ?
C12 C13 . 1.483(3) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C15 C20 . 1.380(3) ?
C15 C16 . 1.382(3) ?
C16 C17 . 1.376(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.378(3) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.376(3) ?
C18 C21 . 1.509(3) ?
C19 C20 . 1.379(3) ?
C19 H19 . 0.9300 ?
C20 H20 . 0.9300 ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 0.9600 ?
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
C16 H16 N2 3_575 0.93 2.60 3.480(3) 158
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
C12 N1 C1 C10 . . . . -0.03(19) ?
C15 N1 C1 C10 . . . . -178.86(14) ?
C12 N1 C1 C2 . . . . 178.88(18) ?
C15 N1 C1 C2 . . . . 0.0(3) ?
N1 C1 C2 C3 . . . . -177.95(18) ?
C10 C1 C2 C3 . . . . 0.8(3) ?
C1 C2 C3 C4 . . . . -0.1(3) ?
C2 C3 C4 C5 . . . . 177.9(2) ?
C2 C3 C4 C9 . . . . -1.2(3) ?
C9 C4 C5 C6 . . . . -0.8(3) ?
C3 C4 C5 C6 . . . . -179.95(19) ?
C4 C5 C6 C7 . . . . -0.4(4) ?
C5 C6 C7 C8 . . . . 1.2(4) ?
C6 C7 C8 C9 . . . . -0.7(3) ?
C7 C8 C9 C4 . . . . -0.6(3) ?
C7 C8 C9 C10 . . . . 177.95(18) ?
C5 C4 C9 C8 . . . . 1.3(3) ?
C3 C4 C9 C8 . . . . -179.57(17) ?
C5 C4 C9 C10 . . . . -177.31(17) ?
C3 C4 C9 C10 . . . . 1.8(3) ?
N1 C1 C10 C9 . . . . 178.82(15) ?
C2 C1 C10 C9 . . . . -0.2(3) ?
N1 C1 C10 C11 . . . . 0.30(19) ?
C2 C1 C10 C11 . . . . -178.68(16) ?
C8 C9 C10 C1 . . . . -179.70(15) ?
C4 C9 C10 C1 . . . . -1.1(2) ?
C8 C9 C10 C11 . . . . -1.7(3) ?
C4 C9 C10 C11 . . . . 176.86(18) ?
C1 C10 C11 C12 . . . . -0.5(2) ?
C9 C10 C11 C12 . . . . -178.67(19) ?
C1 C10 C11 C14 . . . . -177.42(17) ?
C9 C10 C11 C14 . . . . 4.4(3) ?
C14 C11 C12 N1 . . . . 177.53(16) ?
C10 C11 C12 N1 . . . . 0.5(2) ?
C14 C11 C12 C13 . . . . 0.0(3) ?
C10 C11 C12 C13 . . . . -177.0(2) ?
C1 N1 C12 C11 . . . . -0.3(2) ?
C15 N1 C12 C11 . . . . 178.55(16) ?
C1 N1 C12 C13 . . . . 177.43(18) ?
C15 N1 C12 C13 . . . . -3.8(3) ?
C12 C11 C14 N2 . . . . -13E1(3) ?
C10 C11 C14 N2 . . . . 5E1(3) ?
C12 N1 C15 C20 . . . . 110.1(2) ?
C1 N1 C15 C20 . . . . -71.3(2) ?
C12 N1 C15 C16 . . . . -70.1(2) ?
C1 N1 C15 C16 . . . . 108.5(2) ?
C20 C15 C16 C17 . . . . -0.4(3) ?
N1 C15 C16 C17 . . . . 179.90(17) ?
C15 C16 C17 C18 . . . . -0.3(3) ?
C16 C17 C18 C19 . . . . 1.0(3) ?
C16 C17 C18 C21 . . . . -179.8(2) ?
C17 C18 C19 C20 . . . . -0.9(3) ?
C21 C18 C19 C20 . . . . 179.9(2) ?
C18 C19 C20 C15 . . . . 0.3(3) ?
C16 C15 C20 C19 . . . . 0.4(3) ?
N1 C15 C20 C19 . . . . -179.86(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744083
