#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/18/7151851.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_7151851
loop_
_publ_author_name
'Zheng, Zisheng'
'Tang, Lina'
'Fan, Yanfeng'
'Qi, Xiuxiang'
'Du, Yunfei'
'Zhang-Negrerie, Daisy'
_publ_section_title
;
 Oxidative aromatic C-N bond formation: convenient synthesis of
 N-amino-3-nitrile-indoles via FeBr3-mediated intramolecular
 cyclization.
;
_journal_issue                   10
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3714
_journal_page_last               3725
_journal_paper_doi               10.1039/c1ob05069a
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C12 H13 N3'
_chemical_formula_sum            'C12 H13 N3'
_chemical_formula_weight         199.25
_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                99.27(3)
_cell_angle_beta                 96.72(3)
_cell_angle_gamma                118.09(3)
_cell_formula_units_Z            4
_cell_length_a                   8.8268(18)
_cell_length_b                   8.9764(18)
_cell_length_c                   16.501(3)
_cell_measurement_reflns_used    2895
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      2.35
_cell_volume                     1110.1(6)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       ω
_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  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0408
_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       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8940
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         2.99
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3982
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.1123
_refine_ls_R_factor_gt           0.0535
_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)+(0.1156P)²+0.0137P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1461
_refine_ls_wR_factor_ref         0.2100
_reflns_number_gt                2172
_reflns_number_total             3982
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob05069a.txt
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        1110.1(4)
_cod_database_code               7151851
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1519(3) -0.0803(4) 0.09392(18) 0.0660(7) Uani 1 1 d . . .
C2 C 0.0560(4) -0.2202(4) 0.1288(2) 0.0778(9) Uani 1 1 d . . .
H2 H 0.0284 -0.3328 0.1033 0.093 Uiso 1 1 calc R . .
C3 C 0.0037(4) -0.1861(4) 0.2018(2) 0.0808(9) Uani 1 1 d . . .
H3 H -0.0598 -0.2775 0.2257 0.097 Uiso 1 1 calc R . .
C4 C 0.0433(4) -0.0189(4) 0.2408(2) 0.0771(8) Uani 1 1 d . . .
H4 H 0.0057 -0.0007 0.2899 0.093 Uiso 1 1 calc R . .
C5 C 0.1373(4) 0.1203(4) 0.20781(18) 0.0711(8) Uani 1 1 d . . .
H5 H 0.1639 0.2322 0.2338 0.085 Uiso 1 1 calc R . .
C6 C 0.1914(3) 0.0879(4) 0.13418(18) 0.0635(7) Uani 1 1 d . . .
C7 C 0.3015(3) 0.1074(4) 0.01680(18) 0.0664(7) Uani 1 1 d . . .
C8 C 0.2236(4) -0.0640(4) 0.01995(18) 0.0681(7) Uani 1 1 d . . .
C9 C 0.2163(4) -0.1991(4) -0.0417(2) 0.0796(9) Uani 1 1 d . . .
C10 C 0.2355(4) 0.4390(4) 0.0984(2) 0.0848(9) Uani 1 1 d . . .
H10A H 0.1661 0.3963 0.0419 0.127 Uiso 1 1 calc R . .
H10B H 0.2953 0.5640 0.1135 0.127 Uiso 1 1 calc R . .
H10C H 0.1601 0.3946 0.1363 0.127 Uiso 1 1 calc R . .
C11 C 0.5031(4) 0.4657(4) 0.1800(2) 0.0820(9) Uani 1 1 d . . .
H11A H 0.4517 0.4448 0.2281 0.123 Uiso 1 1 calc R . .
H11B H 0.5683 0.5888 0.1848 0.123 Uiso 1 1 calc R . .
H11C H 0.5809 0.4189 0.1776 0.123 Uiso 1 1 calc R . .
C12 C 0.3881(4) 0.1916(4) -0.0479(2) 0.0857(9) Uani 1 1 d . . .
H12A H 0.3080 0.2100 -0.0838 0.129 Uiso 1 1 calc R . .
H12B H 0.4208 0.1177 -0.0809 0.129 Uiso 1 1 calc R . .
H12C H 0.4915 0.3016 -0.0207 0.129 Uiso 1 1 calc R . .
C13 C 1.1012(4) 0.3684(4) 0.43664(17) 0.0659(7) Uani 1 1 d . . .
C14 C 1.2663(4) 0.4905(4) 0.4271(2) 0.0796(9) Uani 1 1 d . . .
H14 H 1.3684 0.5170 0.4642 0.096 Uiso 1 1 calc R . .
C15 C 1.2759(5) 0.5705(4) 0.3623(2) 0.0889(10) Uani 1 1 d . . .
H15 H 1.3848 0.6532 0.3558 0.107 Uiso 1 1 calc R . .
C16 C 1.1229(5) 0.5282(4) 0.3063(2) 0.0884(10) Uani 1 1 d . . .
H16 H 1.1322 0.5862 0.2636 0.106 Uiso 1 1 calc R . .
C17 C 0.9578(5) 0.4037(4) 0.31147(19) 0.0789(9) Uani 1 1 d . . .
H17 H 0.8571 0.3742 0.2724 0.095 Uiso 1 1 calc R . .
C18 C 0.9496(4) 0.3248(4) 0.37770(17) 0.0653(7) Uani 1 1 d . . .
C19 C 0.8629(4) 0.1649(4) 0.47435(17) 0.0653(7) Uani 1 1 d . . .
C20 C 1.0431(4) 0.2676(4) 0.49700(17) 0.0656(7) Uani 1 1 d . . .
C21 C 0.7397(4) 0.0406(4) 0.51675(19) 0.0802(9) Uani 1 1 d . . .
H21A H 0.8056 0.0232 0.5612 0.120 Uiso 1 1 calc R . .
H21B H 0.6625 -0.0688 0.4766 0.120 Uiso 1 1 calc R . .
H21C H 0.6713 0.0869 0.5399 0.120 Uiso 1 1 calc R . .
C22 C 1.1500(4) 0.2739(4) 0.56977(19) 0.0714(8) Uani 1 1 d . . .
C31 C 0.6034(5) -0.0050(5) 0.2778(2) 0.1002(11) Uani 1 1 d . . .
H31A H 0.6607 0.0680 0.2417 0.150 Uiso 1 1 calc R . .
H31B H 0.4799 -0.0766 0.2527 0.150 Uiso 1 1 calc R . .
H31C H 0.6535 -0.0778 0.2850 0.150 Uiso 1 1 calc R . .
C32 C 0.5509(4) 0.2178(5) 0.3562(2) 0.1022(12) Uani 1 1 d . . .
H32A H 0.6117 0.3018 0.3254 0.153 Uiso 1 1 calc R . .
H32B H 0.5624 0.2771 0.4124 0.153 Uiso 1 1 calc R . .
H32C H 0.4286 0.1487 0.3286 0.153 Uiso 1 1 calc R . .
N1 N 0.2845(3) 0.1994(3) 0.08636(14) 0.0664(6) Uani 1 1 d . . .
N2 N 0.3642(3) 0.3815(3) 0.10359(15) 0.0691(6) Uani 1 1 d . . .
N3 N 0.2110(4) -0.3083(4) -0.0908(2) 0.1043(10) Uani 1 1 d . . .
N4 N 0.8065(3) 0.1981(3) 0.40189(14) 0.0680(6) Uani 1 1 d . . .
N5 N 0.6279(3) 0.1037(3) 0.35957(15) 0.0763(7) Uani 1 1 d . . .
N6 N 1.2393(4) 0.2807(4) 0.62855(18) 0.0955(9) Uani 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.3(3) . . ?
C6 C1 C8 106.2(3) . . ?
C2 C1 C8 134.5(3) . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 121.8(3) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 117.8(3) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C5 C6 N1 130.9(3) . . ?
C5 C6 C1 121.8(3) . . ?
N1 C6 C1 107.2(3) . . ?
N1 C7 C8 108.0(3) . . ?
N1 C7 C12 122.1(3) . . ?
C8 C7 C12 130.0(3) . . ?
C7 C8 C9 124.2(3) . . ?
C7 C8 C1 108.5(3) . . ?
C9 C8 C1 127.4(3) . . ?
N3 C9 C8 179.5(4) . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 119.4(3) . . ?
C14 C13 C20 134.0(3) . . ?
C18 C13 C20 106.6(3) . . ?
C15 C14 C13 119.2(3) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 120.1(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 122.7(3) . . ?
C17 C16 H16 118.7 . . ?
C15 C16 H16 118.7 . . ?
C16 C17 C18 116.7(3) . . ?
C16 C17 H17 121.6 . . ?
C18 C17 H17 121.6 . . ?
C17 C18 N4 131.4(3) . . ?
C17 C18 C13 121.9(3) . . ?
N4 C18 C13 106.7(2) . . ?
C20 C19 N4 107.5(3) . . ?
C20 C19 C21 129.9(3) . . ?
N4 C19 C21 122.6(3) . . ?
C19 C20 C22 124.6(3) . . ?
C19 C20 C13 108.8(2) . . ?
C22 C20 C13 126.6(3) . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N6 C22 C20 178.9(4) . . ?
N5 C31 H31A 109.5 . . ?
N5 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N5 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N5 C32 H32A 109.5 . . ?
N5 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
N5 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C7 N1 C6 110.2(2) . . ?
C7 N1 N2 120.8(2) . . ?
C6 N1 N2 128.9(2) . . ?
N1 N2 C10 112.1(2) . . ?
N1 N2 C11 111.6(2) . . ?
C10 N2 C11 115.7(2) . . ?
C19 N4 C18 110.4(2) . . ?
C19 N4 N5 121.1(2) . . ?
C18 N4 N5 128.4(2) . . ?
N4 N5 C31 111.0(2) . . ?
N4 N5 C32 111.8(2) . . ?
C31 N5 C32 114.1(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.404(4) . ?
C1 C2 1.404(4) . ?
C1 C8 1.436(4) . ?
C2 C3 1.380(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(4) . ?
C5 H5 0.9300 . ?
C6 N1 1.390(3) . ?
C7 N1 1.369(3) . ?
C7 C8 1.371(4) . ?
C7 C12 1.484(4) . ?
C8 C9 1.422(4) . ?
C9 N3 1.145(4) . ?
C10 N2 1.452(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 N2 1.457(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.398(4) . ?
C13 C18 1.404(4) . ?
C13 C20 1.430(4) . ?
C14 C15 1.369(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.386(4) . ?
C17 H17 0.9300 . ?
C18 N4 1.400(3) . ?
C19 C20 1.374(4) . ?
C19 N4 1.372(3) . ?
C19 C21 1.484(4) . ?
C20 C22 1.414(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 N6 1.150(3) . ?
C31 N5 1.459(4) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 N5 1.476(4) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
N1 N2 1.403(3) . ?
N4 N5 1.409(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190660
