#------------------------------------------------------------------------------
#$Date: 2025-08-22 15:50:14 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/10/7201048.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_7201048
loop_
_publ_author_name
'Ye, Deju'
'Wang, Jinfang'
'Zhang, Xu'
'Zhou, Yu'
'Ding, Xiao'
'Feng, Enguang'
'Sun, Haifeng'
'Liu, Guannan'
'Jiang, Hualiang'
'Liu, Hong'
_publ_section_title
;
 Gold-catalyzed intramolecular hydroamination of terminal alkynes in
 aqueous media: efficient and regioselective synthesis of
 indole-1-carboxamides
;
_journal_issue                   8
_journal_name_full               'Green Chemistry'
_journal_page_first              1201
_journal_paper_doi               10.1039/b904044g
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C16 H14 N2 O'
_chemical_formula_weight         250.29
_chemical_name_common            N-Benzyl-1H-indole-1-carboxamide
_chemical_name_systematic
;
N-Benzyl-1H-indole-1-carboxamide
;
_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                 97.277(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3034(11)
_cell_length_b                   13.2485(13)
_cell_length_c                   8.9142(9)
_cell_measurement_reflns_used    958
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      39.352
_cell_measurement_theta_min      4.759
_cell_volume                     1324.2(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0989
_diffrn_reflns_av_sigmaI/netI    0.0932
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7163
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79624
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             528
_exptl_crystal_preparation       methanol
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.081
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.878
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2601
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.878
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0299P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1181
_reflns_number_gt                1467
_reflns_number_total             2601
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b904044g.txt
_cod_data_source_block           cd2974
_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 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7201048
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_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
N1 N 0.71414(16) 0.25439(15) 0.9946(2) 0.0575(5) Uani 1 1 d . . .
N3 N 0.90124(14) 0.18593(12) 1.06544(19) 0.0458(5) Uani 1 1 d . . .
O1 O 0.74910(12) 0.15871(11) 1.20634(17) 0.0596(5) Uani 1 1 d . . .
C2 C 0.78311(19) 0.19760(16) 1.0939(3) 0.0485(6) Uani 1 1 d . . .
C4 C 0.95983(19) 0.24309(16) 0.9650(3) 0.0534(6) Uani 1 1 d . . .
H4 H 0.9255 0.2953 0.9047 0.064 Uiso 1 1 calc R . .
C5 C 1.0719(2) 0.21157(18) 0.9688(3) 0.0612(6) Uani 1 1 d . . .
H5 H 1.1285 0.2381 0.9126 0.073 Uiso 1 1 calc R . .
C6 C 1.09049(19) 0.12989(17) 1.0742(3) 0.0535(6) Uani 1 1 d . . .
C7 C 0.98333(18) 0.11492(15) 1.1342(2) 0.0477(6) Uani 1 1 d . . .
C8 C 0.9703(2) 0.03936(17) 1.2386(3) 0.0628(7) Uani 1 1 d . . .
H8 H 0.8981 0.0283 1.2757 0.075 Uiso 1 1 calc R . .
C9 C 1.0695(3) -0.01835(18) 1.2846(3) 0.0779(8) Uani 1 1 d . . .
H9 H 1.0641 -0.0688 1.3560 0.094 Uiso 1 1 calc R . .
C10 C 1.1768(3) -0.0041(2) 1.2286(3) 0.0815(8) Uani 1 1 d . . .
H10 H 1.2418 -0.0447 1.2627 0.098 Uiso 1 1 calc R . .
C11 C 1.1880(2) 0.06914(19) 1.1234(3) 0.0733(7) Uani 1 1 d . . .
H11 H 1.2601 0.0783 1.0852 0.088 Uiso 1 1 calc R . .
C12 C 0.58742(19) 0.27011(18) 1.0061(3) 0.0635(7) Uani 1 1 d . . .
H12A H 0.5675 0.3401 0.9832 0.076 Uiso 1 1 calc R . .
H12B H 0.5730 0.2573 1.1094 0.076 Uiso 1 1 calc R . .
C13 C 0.50687(18) 0.20343(18) 0.9014(2) 0.0534(6) Uani 1 1 d . . .
C14 C 0.5332(2) 0.1041(2) 0.8819(3) 0.0708(7) Uani 1 1 d . . .
H14 H 0.6023 0.0770 0.9344 0.085 Uiso 1 1 calc R . .
C15 C 0.4595(3) 0.0435(2) 0.7859(4) 0.0859(9) Uani 1 1 d . . .
H15 H 0.4791 -0.0240 0.7744 0.103 Uiso 1 1 calc R . .
C16 C 0.3571(2) 0.0818(3) 0.7069(3) 0.0841(9) Uani 1 1 d . . .
H16 H 0.3077 0.0413 0.6407 0.101 Uiso 1 1 calc R . .
C17 C 0.3292(2) 0.1812(3) 0.7277(3) 0.0825(9) Uani 1 1 d . . .
H17 H 0.2599 0.2083 0.6760 0.099 Uiso 1 1 calc R . .
C18 C 0.4030(2) 0.2407(2) 0.8242(3) 0.0689(7) Uani 1 1 d . . .
H18 H 0.3824 0.3077 0.8379 0.083 Uiso 1 1 calc R . .
H1 H 0.7372(18) 0.2749(16) 0.908(3) 0.071(8) Uiso 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C12 121.9(2) . . ?
C2 N1 H1 122.5(14) . . ?
C12 N1 H1 114.5(14) . . ?
C2 N3 C4 126.53(18) . . ?
C2 N3 C7 125.96(18) . . ?
C4 N3 C7 107.50(16) . . ?
O1 C2 N1 124.0(2) . . ?
O1 C2 N3 120.3(2) . . ?
N1 C2 N3 115.7(2) . . ?
C5 C4 N3 109.9(2) . . ?
C5 C4 H4 125.1 . . ?
N3 C4 H4 125.1 . . ?
C4 C5 C6 108.3(2) . . ?
C4 C5 H5 125.8 . . ?
C6 C5 H5 125.8 . . ?
C11 C6 C7 119.2(2) . . ?
C11 C6 C5 133.6(2) . . ?
C7 C6 C5 107.23(19) . . ?
C8 C7 C6 122.0(2) . . ?
C8 C7 N3 130.9(2) . . ?
C6 C7 N3 107.10(19) . . ?
C9 C8 C7 116.7(2) . . ?
C9 C8 H8 121.6 . . ?
C7 C8 H8 121.6 . . ?
C8 C9 C10 122.4(2) . . ?
C8 C9 H9 118.8 . . ?
C10 C9 H9 118.8 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C6 119.3(2) . . ?
C10 C11 H11 120.4 . . ?
C6 C11 H11 120.4 . . ?
N1 C12 C13 113.18(18) . . ?
N1 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
N1 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C18 117.9(2) . . ?
C14 C13 C12 121.3(2) . . ?
C18 C13 C12 120.7(2) . . ?
C13 C14 C15 121.1(2) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 118.6(3) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C13 121.4(3) . . ?
C17 C18 H18 119.3 . . ?
C13 C18 H18 119.3 . . ?
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
N1 C2 1.335(3) . ?
N1 C12 1.464(3) . ?
N1 H1 0.89(2) . ?
N3 C2 1.399(2) . ?
N3 C4 1.401(2) . ?
N3 C7 1.406(2) . ?
O1 C2 1.231(2) . ?
C4 C5 1.330(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.431(3) . ?
C5 H5 0.9300 . ?
C6 C11 1.390(3) . ?
C6 C7 1.399(3) . ?
C7 C8 1.387(3) . ?
C8 C9 1.376(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.382(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.367(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.505(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.365(3) . ?
C13 C18 1.375(3) . ?
C14 C15 1.375(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.369(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.89(2) 2.02(2) 2.889(3) 165.1(19) 4_565
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N1 C2 O1 -4.1(3) . . . . ?
C12 N1 C2 N3 177.50(18) . . . . ?
C4 N3 C2 O1 -164.19(19) . . . . ?
C7 N3 C2 O1 15.1(3) . . . . ?
C4 N3 C2 N1 14.2(3) . . . . ?
C7 N3 C2 N1 -166.48(19) . . . . ?
C2 N3 C4 C5 179.2(2) . . . . ?
C7 N3 C4 C5 -0.2(2) . . . . ?
N3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C11 -179.9(2) . . . . ?
C4 C5 C6 C7 -0.5(3) . . . . ?
C11 C6 C7 C8 -1.8(3) . . . . ?
C5 C6 C7 C8 178.7(2) . . . . ?
C11 C6 C7 N3 179.89(19) . . . . ?
C5 C6 C7 N3 0.4(2) . . . . ?
C2 N3 C7 C8 2.3(3) . . . . ?
C4 N3 C7 C8 -178.3(2) . . . . ?
C2 N3 C7 C6 -179.53(18) . . . . ?
C4 N3 C7 C6 -0.1(2) . . . . ?
C6 C7 C8 C9 2.1(3) . . . . ?
N3 C7 C8 C9 -179.9(2) . . . . ?
C7 C8 C9 C10 -1.2(4) . . . . ?
C8 C9 C10 C11 -0.1(4) . . . . ?
C9 C10 C11 C6 0.5(4) . . . . ?
C7 C6 C11 C10 0.4(4) . . . . ?
C5 C6 C11 C10 179.7(2) . . . . ?
C2 N1 C12 C13 -99.5(3) . . . . ?
N1 C12 C13 C14 42.1(3) . . . . ?
N1 C12 C13 C18 -139.0(2) . . . . ?
C18 C13 C14 C15 1.2(4) . . . . ?
C12 C13 C14 C15 -179.9(2) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C14 C15 C16 C17 -1.0(4) . . . . ?
C15 C16 C17 C18 0.7(4) . . . . ?
C16 C17 C18 C13 0.7(4) . . . . ?
C14 C13 C18 C17 -1.6(3) . . . . ?
C12 C13 C18 C17 179.5(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25946701
2 PubChem 15422552
