#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/89/2238901.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_2238901
loop_
_publ_author_name
'Ruchun, Yang'
'Hui, Zhang'
'BanPeng, Cao'
_publ_section_title
;
 Ethyl N-(3-cyano-1H-indol-2-yl)formimidate
;
_journal_coeditor_code           NG5344
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1745
_journal_paper_doi               10.1107/S1600536813029589
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C12 H11 N3 O'
_chemical_formula_moiety         'C12 H11 N3 O'
_chemical_formula_sum            'C12 H11 N3 O'
_chemical_formula_weight         213.24
_chemical_name_systematic
;
Ethyl N-(3-cyano-1H-indol-2-yl)formimidate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.069(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.7884(6)
_cell_length_b                   8.0546(6)
_cell_length_c                   21.4116(10)
_cell_measurement_reflns_used    1934
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.15
_cell_measurement_theta_min      2.99
_cell_volume                     2200.0(2)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX'
_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  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14358
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.99
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_correction_T_min  0.9974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.187
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         1934
_refine_ls_number_restraints     379
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0402
_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)+(0.0524P)²+0.9005P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1104
_reflns_number_gt                1579
_reflns_number_total             1934
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ng5344.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2238901
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
N N1 0.49318(10) 0.29181(16) 0.48715(6) 0.0443(3) Uani d U 1 1
H H1 0.5435(14) 0.348(2) 0.4722(8) 0.053 Uiso d . 1 1
N N2 0.19409(11) -0.05378(19) 0.46004(7) 0.0594(4) Uani d U 1 1
N N3 0.40141(10) 0.25137(15) 0.38870(6) 0.0452(3) Uani d U 1 1
O O1 0.34656(11) 0.16502(16) 0.29081(6) 0.0700(4) Uani d U 1 1
C C1 0.48809(11) 0.25080(18) 0.54931(7) 0.0421(4) Uani d U 1 1
C C2 0.54626(13) 0.3073(2) 0.60195(8) 0.0529(4) Uani d U 1 1
H H2 0.6022 0.3797 0.5987 0.063 Uiso calc R 1 1
C C3 0.51832(15) 0.2523(2) 0.65929(9) 0.0618(5) Uani d U 1 1
H H3 0.5557 0.2893 0.6955 0.074 Uiso calc R 1 1
C C4 0.43506(15) 0.1423(2) 0.66423(8) 0.0618(5) Uani d U 1 1
H H4 0.4186 0.1061 0.7036 0.074 Uiso calc R 1 1
C C5 0.37706(13) 0.0865(2) 0.61200(8) 0.0525(4) Uani d U 1 1
H H5 0.3214 0.0137 0.6157 0.063 Uiso calc R 1 1
C C6 0.40314(11) 0.14121(17) 0.55334(7) 0.0396(4) Uani d U 1 1
C C7 0.35841(10) 0.11823(17) 0.49076(7) 0.0393(4) Uani d U 1 1
C C8 0.41570(11) 0.21415(17) 0.45158(7) 0.0401(4) Uani d U 1 1
C C9 0.26740(12) 0.02327(19) 0.47287(7) 0.0436(4) Uani d U 1 1
C C10 0.36983(15) 0.1409(2) 0.35136(8) 0.0589(5) Uani d U 1 1
H H10 0.3621 0.0343 0.3670 0.071 Uiso calc R 1 1
C C11 0.35402(15) 0.3329(2) 0.26845(8) 0.0627(5) Uani d U 1 1
H H11A 0.4222 0.3788 0.2814 0.075 Uiso calc R 1 1
H H11B 0.3008 0.4014 0.2857 0.075 Uiso calc R 1 1
C C12 0.33881(17) 0.3308(3) 0.19911(9) 0.0765(6) Uani d U 1 1
H H12A 0.3929 0.2653 0.1823 0.115 Uiso calc R 1 1
H H12B 0.3420 0.4423 0.1834 0.115 Uiso calc R 1 1
H H12C 0.2716 0.2836 0.1867 0.115 Uiso calc R 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'
O O 0.0106 0.0060 '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
C8 N1 C1 110.41(12)
C8 N1 H1 124.4(11)
C1 N1 H1 124.7(11)
C10 N3 C8 119.12(14)
C10 O1 C11 116.60(14)
N1 C1 C2 130.48(14)
N1 C1 C6 107.42(13)
C2 C1 C6 121.97(15)
C3 C2 C1 117.56(16)
C3 C2 H2 121.2
C1 C2 H2 121.2
C2 C3 C4 121.33(16)
C2 C3 H3 119.3
C4 C3 H3 119.3
C5 C4 C3 121.14(16)
C5 C4 H4 119.4
C3 C4 H4 119.4
C4 C5 C6 118.74(15)
C4 C5 H5 120.6
C6 C5 H5 120.6
C5 C6 C1 119.25(14)
C5 C6 C7 134.24(14)
C1 C6 C7 106.42(13)
C8 C7 C9 126.43(14)
C8 C7 C6 107.52(12)
C9 C7 C6 125.92(13)
N1 C8 N3 119.22(13)
N1 C8 C7 108.23(13)
N3 C8 C7 132.25(13)
N2 C9 C7 178.31(16)
N3 C10 O1 124.39(16)
N3 C10 H10 117.8
O1 C10 H10 117.8
O1 C11 C12 108.37(16)
O1 C11 H11A 110.0
C12 C11 H11A 110.0
O1 C11 H11B 110.0
C12 C11 H11B 110.0
H11A C11 H11B 108.4
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C8 1.3587(19)
N1 C1 1.377(2)
N1 H1 0.866(18)
N2 C9 1.1415(19)
N3 C10 1.244(2)
N3 C8 1.379(2)
O1 C10 1.324(2)
O1 C11 1.440(2)
C1 C2 1.383(2)
C1 C6 1.407(2)
C2 C3 1.376(2)
C2 H2 0.9300
C3 C4 1.395(3)
C3 H3 0.9300
C4 C5 1.373(2)
C4 H4 0.9300
C5 C6 1.393(2)
C5 H5 0.9300
C6 C7 1.431(2)
C7 C8 1.387(2)
C7 C9 1.422(2)
C10 H10 0.9300
C11 C12 1.484(3)
C11 H11A 0.9700
C11 H11B 0.9700
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 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
_geom_hbond_publ_flag
N1 H1 N2 3 0.87(2) 2.12(2) 2.9490(19) 161(2) yes
