#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/25/2222560.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_2222560
loop_
_publ_author_name
'Siddiquee, Tasneem'
'Islam, Shahid'
'Bennett, Dennis'
'Zeller, Matthias'
'Hossain, Mahmun'
_publ_section_title
;
 Ethyl 1-acetyl-1H-indole-3-carboxylate
;
_journal_coeditor_code           BH2233
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1802
_journal_page_last               o1803
_journal_paper_doi               10.1107/S1600536809025379
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H13 N O3'
_chemical_formula_moiety         'C13 H13 N O3'
_chemical_formula_sum            'C13 H13 N O3'
_chemical_formula_weight         231.24
_chemical_name_systematic
;
Ethyl 1-acetyl-1H-indole-3-carboxylate
;
_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                97.380(10)
_cell_angle_beta                 95.78(2)
_cell_angle_gamma                114.280(10)
_cell_formula_units_Z            2
_cell_length_a                   7.5190(10)
_cell_length_b                   8.4790(10)
_cell_length_c                   10.187(2)
_cell_measurement_reflns_used    23
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      11.35
_cell_measurement_theta_min      3.68
_cell_volume                     578.58(17)
_computing_cell_refinement       'XSCANS (Siemens, 1996)'
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        'XSCANS (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution
'XPREP (Siemens 1994) and SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       2θ/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  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2536
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.05
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[XSCANS (Siemens 1996) and XPREP (Siemens, 1994)]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.180
_refine_ls_extinction_coef       0.103(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Bruker, 2003; Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2027
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0422
_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)+(0.0647P)²+0.0738P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1202
_reflns_number_gt                1696
_reflns_number_total             2027
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2233.cif
_cod_data_source_block           I
_cod_original_cell_volume        578.58(15)
_cod_database_code               2222560
_cod_database_fobs_code          2222560
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_disorder_assembly
_atom_site_disorder_group
C C1 0.3179(2) 0.9158(2) 0.76860(15) 0.0474(4) Uani d . 1 . .
C C2 0.3276(2) 0.8319(2) 0.64495(16) 0.0560(4) Uani d . 1 . .
H H2 0.3926 0.8952 0.5826 0.067 Uiso calc R 1 . .
C C3 0.2364(3) 0.6502(2) 0.61896(18) 0.0641(5) Uani d . 1 . .
H H3 0.2402 0.5898 0.5371 0.077 Uiso calc R 1 . .
C C4 0.1394(3) 0.5554(2) 0.71141(19) 0.0658(5) Uani d . 1 . .
H H4 0.0804 0.4330 0.6907 0.079 Uiso calc R 1 . .
C C5 0.1286(3) 0.6392(2) 0.83389(17) 0.0572(4) Uani d . 1 . .
H H5 0.0629 0.5747 0.8955 0.069 Uiso calc R 1 . .
C C6 0.2186(2) 0.8227(2) 0.86285(15) 0.0477(4) Uani d . 1 . .
C C7 0.2359(2) 0.9517(2) 0.97738(15) 0.0477(4) Uani d . 1 . .
C C8 0.3421(2) 1.1130(2) 0.95024(15) 0.0491(4) Uani d . 1 . .
H H8 0.3747 1.2189 1.0077 0.059 Uiso calc R 1 . .
C C9 0.1539(2) 0.9133(2) 1.10037(16) 0.0526(4) Uani d . 1 . .
C C10 0.5038(3) 1.2371(2) 0.76197(16) 0.0563(4) Uani d . 1 . .
C C11 0.5648(3) 1.4194(3) 0.8383(2) 0.0756(6) Uani d . 1 . .
H H11A 0.6392 1.4336 0.9248 0.113 Uiso calc R 1 . .
H H11B 0.4491 1.4377 0.8497 0.113 Uiso calc R 1 . .
H H11C 0.6452 1.5037 0.7894 0.113 Uiso calc R 1 . .
C C12 0.1351(3) 1.0333(3) 1.31867(17) 0.0613(5) Uani d . 1 . .
H H12A 0.1950 0.9683 1.3634 0.074 Uiso calc R 1 . .
H H12B -0.0076 0.9667 1.3045 0.074 Uiso calc R 1 . .
C C13 0.1950(3) 1.2107(3) 1.40273(18) 0.0724(5) Uani d . 1 . .
H H13A 0.1508 1.1970 1.4875 0.109 Uiso calc R 1 . .
H H13B 0.1361 1.2743 1.3572 0.109 Uiso calc R 1 . .
H H13C 0.3366 1.2747 1.4175 0.109 Uiso calc R 1 . .
N N1 0.39555(19) 1.09788(17) 0.82406(12) 0.0489(4) Uani d . 1 . .
O O1 0.0559(3) 0.76795(18) 1.11828(14) 0.0845(5) Uani d . 1 . .
O O2 0.20161(17) 1.05915(15) 1.19112(11) 0.0559(3) Uani d . 1 . .
O O3 0.5434(2) 1.20764(19) 0.65295(13) 0.0814(5) Uani d . 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 122.32(15) ?
C2 C1 N1 . . 130.20(15) ?
C6 C1 N1 . . 107.48(13) ?
C3 C2 C1 . . 116.89(17) ?
C3 C2 H2 . . 121.6 ?
C1 C2 H2 . . 121.6 ?
C2 C3 C4 . . 121.75(17) ?
C2 C3 H3 . . 119.1 ?
C4 C3 H3 . . 119.1 ?
C5 C4 C3 . . 121.27(17) ?
C5 C4 H4 . . 119.4 ?
C3 C4 H4 . . 119.4 ?
C4 C5 C6 . . 118.33(17) ?
C4 C5 H5 . . 120.8 ?
C6 C5 H5 . . 120.8 ?
C5 C6 C1 . . 119.44(14) ?
C5 C6 C7 . . 133.47(15) ?
C1 C6 C7 . . 107.10(14) ?
C8 C7 C6 . . 107.50(14) ?
C8 C7 C9 . . 126.52(15) ?
C6 C7 C9 . . 125.98(15) ?
C7 C8 N1 . . 110.33(14) ?
C7 C8 H8 . . 124.8 ?
N1 C8 H8 . . 124.8 ?
O1 C9 O2 . . 123.51(15) ?
O1 C9 C7 . . 124.06(16) ?
O2 C9 C7 . . 112.43(14) ?
O3 C10 N1 . . 120.26(16) ?
O3 C10 C11 . . 123.11(16) ?
N1 C10 C11 . . 116.63(15) ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
O2 C12 C13 . . 107.88(15) ?
O2 C12 H12A . . 110.1 ?
C13 C12 H12A . . 110.1 ?
O2 C12 H12B . . 110.1 ?
C13 C12 H12B . . 110.1 ?
H12A C12 H12B . . 108.4 ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C8 N1 C10 . . 126.27(14) ?
C8 N1 C1 . . 107.60(13) ?
C10 N1 C1 . . 126.12(13) ?
C9 O2 C12 . . 116.25(13) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.389(2) ?
C1 C6 . 1.399(2) ?
C1 N1 . 1.4186(19) ?
C2 C3 . 1.379(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.384(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.381(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.393(2) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.449(2) ?
C7 C8 . 1.352(2) ?
C7 C9 . 1.467(2) ?
C8 N1 . 1.391(2) ?
C8 H8 . 0.9300 ?
C9 O1 . 1.197(2) ?
C9 O2 . 1.3367(19) ?
C10 O3 . 1.201(2) ?
C10 N1 . 1.400(2) ?
C10 C11 . 1.497(3) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 O2 . 1.449(2) ?
C12 C13 . 1.494(3) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 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
C2 H2 O3 2_676 0.93 2.61 3.296(2) 131 yes
C5 H5 O1 2_567 0.93 2.64 3.273(2) 125 yes
C12 H12B Cg1 2_577 0.96 2.95 3.618(3) 127 y
C13 H13B Cg2 2_577 0.96 2.78 3.587(3) 142 y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.9(2) ?
N1 C1 C2 C3 . . . . -179.95(15) ?
C1 C2 C3 C4 . . . . 0.1(3) ?
C2 C3 C4 C5 . . . . 0.5(3) ?
C3 C4 C5 C6 . . . . -0.2(3) ?
C4 C5 C6 C1 . . . . -0.6(2) ?
C4 C5 C6 C7 . . . . 179.54(17) ?
C2 C1 C6 C5 . . . . 1.2(2) ?
N1 C1 C6 C5 . . . . -179.57(13) ?
C2 C1 C6 C7 . . . . -178.95(14) ?
N1 C1 C6 C7 . . . . 0.31(16) ?
C5 C6 C7 C8 . . . . 179.58(17) ?
C1 C6 C7 C8 . . . . -0.29(17) ?
C5 C6 C7 C9 . . . . 0.0(3) ?
C1 C6 C7 C9 . . . . -179.90(14) ?
C6 C7 C8 N1 . . . . 0.15(18) ?
C9 C7 C8 N1 . . . . 179.76(14) ?
C8 C7 C9 O1 . . . . 177.82(17) ?
C6 C7 C9 O1 . . . . -2.6(3) ?
C8 C7 C9 O2 . . . . -2.5(2) ?
C6 C7 C9 O2 . . . . 177.09(13) ?
C7 C8 N1 C10 . . . . 179.14(15) ?
C7 C8 N1 C1 . . . . 0.04(17) ?
O3 C10 N1 C8 . . . . 179.02(16) ?
C11 C10 N1 C8 . . . . -1.0(3) ?
O3 C10 N1 C1 . . . . -2.1(3) ?
C11 C10 N1 C1 . . . . 177.96(15) ?
C2 C1 N1 C8 . . . . 178.95(16) ?
C6 C1 N1 C8 . . . . -0.23(16) ?
C2 C1 N1 C10 . . . . -0.1(3) ?
C6 C1 N1 C10 . . . . -179.32(15) ?
O1 C9 O2 C12 . . . . 2.7(2) ?
C7 C9 O2 C12 . . . . -177.03(13) ?
C13 C12 O2 C9 . . . . -177.54(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742749
