#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/31/2233170.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_2233170
loop_
_publ_author_name
'Ge, Yu-Hua'
'Pan, Mei-Ling'
'Xu, Jian'
'Luo, Yang-Hui'
_publ_section_title
;
 2-(7-Methyl-1H-indol-3-yl)acetonitrile
;
_journal_coeditor_code           HB6546
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o141
_journal_paper_doi               10.1107/S1600536811053396
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C11 H10 N2'
_chemical_formula_moiety         'C11 H10 N2'
_chemical_formula_sum            'C11 H10 N2'
_chemical_formula_weight         170.21
_chemical_name_systematic
;
2-(7-Methyl-1H-indol-3-yl)acetonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 97.97(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9962(14)
_cell_length_b                   8.9445(18)
_cell_length_c                   15.406(3)
_cell_measurement_reflns_used    2175
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.450
_cell_measurement_theta_min      2.7
_cell_volume                     954.8(3)
_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_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku SCXmini CCD'
_diffrn_measurement_method       'ω 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  0.0576
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9402
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.51
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.171
_refine_ls_extinction_coef       0
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0546
_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)+(0.0708P)²+0.0707P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1360
_refine_ls_wR_factor_ref         0.1535
_reflns_number_gt                1418
_reflns_number_total             2160
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6546.cif
_cod_data_source_block           I
_cod_original_cell_volume        954.7(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2233170
_cod_database_fobs_code          2233170
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
C C1 -0.0179(3) 0.6121(2) 0.21424(12) 0.0587(5) Uani d . 1 1
H H1B -0.1278 0.6642 0.1903 0.070 Uiso calc R 1 1
C C2 0.0270(2) 0.57655(18) 0.30000(11) 0.0511(4) Uani d . 1 1
C C3 0.2072(2) 0.49843(17) 0.30912(10) 0.0473(4) Uani d . 1 1
C C4 0.3276(3) 0.43296(19) 0.37953(12) 0.0613(5) Uani d . 1 1
H H4A 0.2955 0.4369 0.4361 0.074 Uiso calc R 1 1
C C5 0.4936(3) 0.3631(2) 0.36311(16) 0.0758(6) Uani d . 1 1
H H5A 0.5736 0.3187 0.4092 0.091 Uiso calc R 1 1
C C6 0.5451(3) 0.3571(2) 0.27861(17) 0.0768(6) Uani d . 1 1
H H6A 0.6588 0.3088 0.2703 0.092 Uiso calc R 1 1
C C7 0.4334(3) 0.4204(2) 0.20730(13) 0.0644(5) Uani d . 1 1
C C8 0.2629(2) 0.48979(17) 0.22467(10) 0.0506(4) Uani d . 1 1
C C9 0.4896(4) 0.4170(3) 0.11583(16) 0.0958(8) Uani d . 1 1
H H9A 0.6091 0.3639 0.1168 0.144 Uiso calc R 1 1
H H9B 0.5047 0.5175 0.0959 0.144 Uiso calc R 1 1
H H9C 0.3905 0.3676 0.0768 0.144 Uiso calc R 1 1
C C10 -0.0948(3) 0.6089(2) 0.37116(13) 0.0678(5) Uani d . 1 1
H H10A -0.2171 0.6509 0.3449 0.081 Uiso calc R 1 1
H H10B -0.1216 0.5158 0.3994 0.081 Uiso calc R 1 1
C C11 -0.0021(3) 0.7128(2) 0.43771(12) 0.0621(5) Uani d . 1 1
N N1 0.1212(2) 0.56067(16) 0.16799(9) 0.0600(4) Uani d . 1 1
H H1A 0.1207 0.5707 0.1124 0.072 Uiso calc R 1 1
N N2 0.0698(3) 0.7913(2) 0.48993(11) 0.0856(6) 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
C2 C1 N1 110.17(15)
C2 C1 H1B 124.9
N1 C1 H1B 124.9
C1 C2 C3 107.04(15)
C1 C2 C10 125.94(16)
C3 C2 C10 126.99(15)
C4 C3 C8 118.43(16)
C4 C3 C2 134.80(16)
C8 C3 C2 106.76(14)
C5 C4 C3 118.63(18)
C5 C4 H4A 120.7
C3 C4 H4A 120.7
C4 C5 C6 121.50(19)
C4 C5 H5A 119.2
C6 C5 H5A 119.2
C7 C6 C5 122.37(19)
C7 C6 H6A 118.8
C5 C6 H6A 118.8
C6 C7 C8 115.63(18)
C6 C7 C9 122.82(19)
C8 C7 C9 121.5(2)
N1 C8 C7 129.60(17)
N1 C8 C3 106.97(15)
C7 C8 C3 123.43(17)
C7 C9 H9A 109.5
C7 C9 H9B 109.5
H9A C9 H9B 109.5
C7 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C11 C10 C2 112.97(15)
C11 C10 H10A 109.0
C2 C10 H10A 109.0
C11 C10 H10B 109.0
C2 C10 H10B 109.0
H10A C10 H10B 107.8
N2 C11 C10 179.0(2)
C1 N1 C8 109.06(14)
C1 N1 H1A 125.5
C8 N1 H1A 125.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.353(2)
C1 N1 1.364(2)
C1 H1B 0.9300
C2 C3 1.431(2)
C2 C10 1.507(2)
C3 C4 1.405(2)
C3 C8 1.411(2)
C4 C5 1.373(3)
C4 H4A 0.9300
C5 C6 1.399(3)
C5 H5A 0.9300
C6 C7 1.378(3)
C6 H6A 0.9300
C7 C8 1.403(2)
C7 C9 1.515(3)
C8 N1 1.381(2)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 C11 1.467(3)
C10 H10A 0.9700
C10 H10B 0.9700
C11 N2 1.131(2)
N1 H1A 0.8600
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 4_575 0.86 2.24 3.022(2) 151
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21395138
