#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/70/2207086.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_2207086
loop_
_publ_author_name
'T. Ravishankar'
'K. Chinnakali'
'N. Arumugam'
'P. C. Srinivasan'
'Anwar Usman'
'Hoong-Kun Fun'
_publ_section_title
;
 2-(2-Acetamido-5-methylbenzoyl)-1H-indole
;
_journal_coeditor_code           WN6372
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3291
_journal_page_last               o3293
_journal_paper_doi               10.1107/S160053680502893X
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C18 H16 N2 O2'
_chemical_formula_moiety         'C18 H16 N2 O2'
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33
_chemical_name_systematic
;
2-(2-Acetamido-5-methylbenzoyl)indole
;
_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                 107.0500(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.8765(12)
_cell_length_b                   14.3774(8)
_cell_length_c                   11.7603(7)
_cell_measurement_reflns_used    2509
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.28
_cell_volume                     3536.4(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 2003)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_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  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0573
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8691
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.28
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.250
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3108
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.1088
_refine_ls_R_factor_gt           0.0766
_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)+(0.1234P)²+0.2753P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2021
_refine_ls_wR_factor_ref         0.2164
_reflns_number_gt                2067
_reflns_number_total             3108
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn6372.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2207086
_cod_database_fobs_code          2207086
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_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_type_symbol
O1 0.24259(12) -0.00154(16) 0.3462(2) 0.0524(7) Uani d . 1 O
O2 0.34245(13) 0.28941(17) 0.2779(2) 0.0543(7) Uani d . 1 O
N1 0.14819(12) -0.08089(17) 0.4111(2) 0.0356(7) Uani d . 1 N
H1N 0.1565 -0.1067 0.3514 0.043 Uiso calc R 1 H
N2 0.30328(13) 0.15428(19) 0.3295(2) 0.0422(7) Uani d . 1 N
H2N 0.2858 0.1028 0.2995 0.051 Uiso calc R 1 H
C1 0.18169(14) -0.0079(2) 0.4763(2) 0.0304(7) Uani d . 1 C
C2 0.15435(15) 0.0146(2) 0.5644(3) 0.0346(8) Uani d . 1 C
H2 0.1674 0.0619 0.6203 0.042 Uiso calc R 1 H
C3 0.10267(15) -0.0478(2) 0.5542(3) 0.0356(8) Uani d . 1 C
C4 0.05740(17) -0.0600(3) 0.6168(3) 0.0506(10) Uani d . 1 C
H4 0.0581 -0.0225 0.6817 0.061 Uiso calc R 1 H
C5 0.01238(17) -0.1282(3) 0.5803(4) 0.0607(11) Uani d . 1 C
H5 -0.0174 -0.1374 0.6216 0.073 Uiso calc R 1 H
C6 0.01010(17) -0.1845(3) 0.4820(4) 0.0596(11) Uani d . 1 C
H6 -0.0215 -0.2297 0.4591 0.072 Uiso calc R 1 H
C7 0.05319(16) -0.1745(3) 0.4189(3) 0.0477(9) Uani d . 1 C
H7 0.0515 -0.2120 0.3536 0.057 Uiso calc R 1 H
C8 0.09963(14) -0.1060(2) 0.4564(3) 0.0354(8) Uani d . 1 C
C9 0.23494(15) 0.0302(2) 0.4387(3) 0.0337(7) Uani d . 1 C
C10 0.27804(14) 0.1041(2) 0.5082(3) 0.0309(7) Uani d . 1 C
C11 0.28902(15) 0.1123(2) 0.6301(3) 0.0375(8) Uani d . 1 C
H11 0.2698 0.0696 0.6682 0.045 Uiso calc R 1 H
C12 0.32714(15) 0.1807(2) 0.6976(3) 0.0397(8) Uani d . 1 C
C13 0.35524(16) 0.2434(3) 0.6376(3) 0.0455(9) Uani d . 1 C
H13 0.3802 0.2916 0.6798 0.055 Uiso calc R 1 H
C14 0.34708(16) 0.2359(2) 0.5181(3) 0.0404(8) Uani d . 1 C
H14 0.3668 0.2787 0.4810 0.049 Uiso calc R 1 H
C15 0.31024(14) 0.1661(2) 0.4515(3) 0.0328(7) Uani d . 1 C
C16 0.3385(2) 0.1880(3) 0.8305(3) 0.0684(13) Uani d . 1 C
H16A 0.3153 0.1397 0.8562 0.103 Uiso calc R 1 H
H16B 0.3240 0.2476 0.8492 0.103 Uiso calc R 1 H
H16C 0.3833 0.1815 0.8705 0.103 Uiso calc R 1 H
C17 0.31985(16) 0.2116(2) 0.2520(3) 0.0401(8) Uani d . 1 C
C18 0.3090(2) 0.1711(3) 0.1300(3) 0.0627(12) Uani d . 1 C
H18A 0.3190 0.2168 0.0787 0.094 Uiso calc R 1 H
H18B 0.2650 0.1529 0.0987 0.094 Uiso calc R 1 H
H18C 0.3359 0.1176 0.1347 0.094 Uiso calc R 1 H
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_publ_flag
C8 N1 C1 109.4(2) ?
C8 N1 H1N 125.3 ?
C1 N1 H1N 125.3 ?
C17 N2 C15 129.9(3) y
C17 N2 H2N 115.0 ?
C15 N2 H2N 115.0 ?
N1 C1 C2 108.6(3) ?
N1 C1 C9 117.2(2) ?
C2 C1 C9 134.2(3) ?
C1 C2 C3 107.3(3) ?
C1 C2 H2 126.3 ?
C3 C2 H2 126.3 ?
C8 C3 C4 118.7(3) ?
C8 C3 C2 106.9(3) ?
C4 C3 C2 134.3(3) ?
C5 C4 C3 118.5(3) ?
C5 C4 H4 120.7 ?
C3 C4 H4 120.7 ?
C4 C5 C6 121.5(3) ?
C4 C5 H5 119.2 ?
C6 C5 H5 119.2 ?
C7 C6 C5 121.6(3) ?
C7 C6 H6 119.2 ?
C5 C6 H6 119.2 ?
C6 C7 C8 117.2(3) ?
C6 C7 H7 121.4 ?
C8 C7 H7 121.4 ?
N1 C8 C7 129.9(3) ?
N1 C8 C3 107.7(3) ?
C7 C8 C3 122.4(3) ?
O1 C9 C1 116.9(3) y
O1 C9 C10 121.2(3) ?
C1 C9 C10 122.0(3) y
C11 C10 C15 118.2(3) ?
C11 C10 C9 121.1(3) ?
C15 C10 C9 120.7(3) ?
C12 C11 C10 123.2(3) ?
C12 C11 H11 118.4 ?
C10 C11 H11 118.4 ?
C11 C12 C13 116.8(3) y
C11 C12 C16 122.2(3) y
C13 C12 C16 121.0(3) ?
C14 C13 C12 121.7(3) ?
C14 C13 H13 119.2 ?
C12 C13 H13 119.2 ?
C13 C14 C15 121.3(3) ?
C13 C14 H14 119.3 ?
C15 C14 H14 119.3 ?
C14 C15 N2 122.5(3) ?
C14 C15 C10 118.6(3) ?
N2 C15 C10 118.9(3) ?
C12 C16 H16A 109.5 ?
C12 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
C12 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
O2 C17 N2 123.8(3) y
O2 C17 C18 122.1(3) ?
N2 C17 C18 114.1(3) y
C17 C18 H18A 109.5 ?
C17 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
C17 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C9 1.235(3) y
O2 C17 1.225(4) y
N1 C8 1.369(4) ?
N1 C1 1.377(4) ?
N1 H1N 0.86 ?
N2 C17 1.355(4) y
N2 C15 1.408(4) y
N2 H2N 0.86 ?
C1 C2 1.379(4) ?
C1 C9 1.468(4) ?
C2 C3 1.420(4) ?
C2 H2 0.93 ?
C3 C8 1.408(4) ?
C3 C4 1.408(5) ?
C4 C5 1.367(5) ?
C4 H4 0.93 ?
C5 C6 1.399(5) ?
C5 H5 0.93 ?
C6 C7 1.368(5) ?
C6 H6 0.93 ?
C7 C8 1.391(4) ?
C7 H7 0.93 ?
C9 C10 1.495(4) ?
C10 C11 1.387(4) ?
C10 C15 1.418(4) ?
C11 C12 1.380(4) ?
C11 H11 0.93 ?
C12 C13 1.394(4) ?
C12 C16 1.513(4) ?
C13 C14 1.367(4) ?
C13 H13 0.93 ?
C14 C15 1.379(4) ?
C14 H14 0.93 ?
C16 H16A 0.96 ?
C16 H16B 0.96 ?
C16 H16C 0.96 ?
C17 C18 1.501(4) ?
C18 H18A 0.96 ?
C18 H18B 0.96 ?
C18 H18C 0.96 ?
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 H1N O2 4_545 0.86 2.14 2.954(3) 159
N2 H2N O1 . 0.86 1.94 2.641(4) 138
C2 H2 O2 7_556 0.93 2.49 3.363(4) 156
C11 H11 O1 6_556 0.93 2.53 3.397(4) 154
C14 H14 O2 . 0.93 2.29 2.901(4) 122
C16 H16A O1 6_556 0.96 2.53 3.442(5) 160
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_publ_flag
C8 N1 C1 C2 -0.1(3) ?
C8 N1 C1 C9 -178.5(3) ?
N1 C1 C2 C3 0.8(3) ?
C9 C1 C2 C3 178.8(3) ?
C1 C2 C3 C8 -1.2(3) ?
C1 C2 C3 C4 179.9(4) ?
C8 C3 C4 C5 0.1(5) ?
C2 C3 C4 C5 178.9(4) ?
C3 C4 C5 C6 -0.8(6) ?
C4 C5 C6 C7 0.7(6) ?
C5 C6 C7 C8 0.0(6) ?
C1 N1 C8 C7 178.9(3) ?
C1 N1 C8 C3 -0.6(3) ?
C6 C7 C8 N1 179.9(3) ?
C6 C7 C8 C3 -0.7(5) ?
C4 C3 C8 N1 -179.8(3) ?
C2 C3 C8 N1 1.1(3) ?
C4 C3 C8 C7 0.6(5) ?
C2 C3 C8 C7 -178.5(3) ?
N1 C1 C9 O1 5.3(4) ?
C2 C1 C9 O1 -172.6(3) ?
N1 C1 C9 C10 -174.9(3) ?
C2 C1 C9 C10 7.2(5) ?
O1 C9 C10 C11 -152.0(3) ?
C1 C9 C10 C11 28.2(4) ?
O1 C9 C10 C15 26.2(5) ?
C1 C9 C10 C15 -153.6(3) ?
C15 C10 C11 C12 3.4(5) ?
C9 C10 C11 C12 -178.4(3) ?
C10 C11 C12 C13 0.0(5) ?
C10 C11 C12 C16 -179.9(3) ?
C11 C12 C13 C14 -2.0(5) ?
C16 C12 C13 C14 177.9(4) ?
C12 C13 C14 C15 0.4(6) ?
C13 C14 C15 N2 -177.2(3) ?
C13 C14 C15 C10 3.0(5) ?
C17 N2 C15 C14 -11.9(5) y
C17 N2 C15 C10 167.9(3) ?
C11 C10 C15 C14 -4.8(4) ?
C9 C10 C15 C14 176.9(3) ?
C11 C10 C15 N2 175.4(3) ?
C9 C10 C15 N2 -2.8(4) ?
C15 N2 C17 O2 -3.5(6) y
C15 N2 C17 C18 175.7(3) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9295015
