#------------------------------------------------------------------------------
#$Date: 2016-06-18 04:19:11 +0300 (Sat, 18 Jun 2016) $
#$Revision: 183679 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/17/2241722.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_2241722
loop_
_publ_author_name
'Kerr, Jamie R.'
'Trembleau, Laurent'
'Storey, John M. D.'
'Wardell, James L.'
'Harrison, William T. A.'
_publ_section_title
;
 Weak interactions in the crystal structures of two indole derivatives
;
_journal_coeditor_code           SJ5499
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              964
_journal_page_last               968
_journal_paper_doi               10.1107/S2056989016008616
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C11 H10 Cl N O2'
_chemical_formula_moiety         'C11 H10 Cl N O2'
_chemical_formula_sum            'C11 H10 Cl N O2'
_chemical_formula_weight         223.65
_chemical_name_systematic
;
Ethyl 5-chloro-1H-indole-2-carboxylate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 97.464(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7168(6)
_cell_length_b                   4.57830(10)
_cell_length_c                   16.5929(11)
_cell_measurement_reflns_used    6396
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     1033.20(9)
_computing_cell_refinement
;
CrystalClear (Rigaku, 2012)
;
_computing_data_collection
;
CrystalClear (Rigaku, 2012)
;
_computing_data_reduction
;
CrystalClear (Rigaku, 2012)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and ATOMS (Dowty, 2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7035
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.455
_diffrn_reflns_theta_min         2.995
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrystalClear; Rigaku, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       rod
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.229
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2340
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0309
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0408P)²+0.4177P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0821
_reflns_number_gt                2051
_reflns_number_total             2340
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sj5499sup1.cif
_cod_data_source_block           I
_cod_database_code               2241722
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_occupancy
C C1 0.52594(9) 0.5040(3) 0.35005(8) 0.0142(3) Uani d 1
C C2 0.62255(10) 0.4033(3) 0.35004(8) 0.0176(3) Uani d 1
H H2 0.6742 0.4669 0.3899 0.021 Uiso calc 1
C C3 0.63988(9) 0.2090(3) 0.29013(8) 0.0171(3) Uani d 1
H H3 0.7044 0.1360 0.2883 0.021 Uiso calc 1
C C4 0.56188(10) 0.1181(3) 0.23127(8) 0.0153(3) Uani d 1
C C5 0.46670(9) 0.2127(3) 0.23045(8) 0.0146(3) Uani d 1
H H5 0.4157 0.1459 0.1905 0.017 Uiso calc 1
C C6 0.44761(9) 0.4121(3) 0.29091(8) 0.0134(3) Uani d 1
C C7 0.36151(9) 0.5605(3) 0.30827(8) 0.0136(3) Uani d 1
H H7 0.2972 0.5434 0.2795 0.016 Uiso calc 1
C C8 0.38999(9) 0.7341(3) 0.37519(7) 0.0135(3) Uani d 1
C C9 0.33337(9) 0.9388(3) 0.41806(7) 0.0133(3) Uani d 1
C C10 0.17639(10) 1.1516(3) 0.42258(8) 0.0174(3) Uani d 1
H H10A 0.1186 1.2025 0.3829 0.021 Uiso calc 1
H H10B 0.2134 1.3334 0.4376 0.021 Uiso calc 1
C C11 0.14202(11) 1.0204(4) 0.49746(9) 0.0271(3) Uani d 1
H H11A 0.1002 1.1610 0.5214 0.041 Uiso calc 1
H H11B 0.1044 0.8421 0.4825 0.041 Uiso calc 1
H H11C 0.1991 0.9728 0.5371 0.041 Uiso calc 1
N N1 0.48871(8) 0.6981(3) 0.40047(7) 0.0147(2) Uani d 1
H H1 0.5235(12) 0.789(4) 0.4411(10) 0.018 Uiso d 1
O O1 0.23886(6) 0.9493(2) 0.38517(5) 0.0152(2) Uani d 1
O O2 0.36753(7) 1.0841(2) 0.47654(6) 0.0184(2) Uani d 1
Cl Cl1 0.58935(2) -0.12275(8) 0.15557(2) 0.01929(11) 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'
Cl Cl 0.1484 0.1585 '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
N1 C1 C2 130.00(12)
N1 C1 C6 107.86(11)
C2 C1 C6 122.13(13)
C3 C2 C1 117.63(12)
C3 C2 H2 121.2
C1 C2 H2 121.2
C2 C3 C4 120.17(12)
C2 C3 H3 119.9
C4 C3 H3 119.9
C5 C4 C3 123.13(12)
C5 C4 Cl1 119.00(10)
C3 C4 Cl1 117.87(10)
C4 C5 C6 117.55(12)
C4 C5 H5 121.2
C6 C5 H5 121.2
C5 C6 C1 119.38(12)
C5 C6 C7 133.66(12)
C1 C6 C7 106.95(11)
C8 C7 C6 106.38(11)
C8 C7 H7 126.8
C6 C7 H7 126.8
N1 C8 C7 109.96(12)
N1 C8 C9 119.57(11)
C7 C8 C9 130.46(12)
O2 C9 O1 123.78(12)
O2 C9 C8 124.37(12)
O1 C9 C8 111.85(11)
O1 C10 C11 111.24(12)
O1 C10 H10A 109.4
C11 C10 H10A 109.4
O1 C10 H10B 109.4
C11 C10 H10B 109.4
H10A C10 H10B 108.0
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
C1 N1 C8 108.85(11)
C1 N1 H1 124.7(11)
C8 N1 H1 126.4(11)
C9 O1 C10 116.19(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.3644(18)
C1 C2 1.4032(18)
C1 C6 1.4215(17)
C2 C3 1.3774(19)
C2 H2 0.9500
C3 C4 1.4145(19)
C3 H3 0.9500
C4 C5 1.3739(18)
C4 Cl1 1.7488(14)
C5 C6 1.4059(18)
C5 H5 0.9500
C6 C7 1.4240(18)
C7 C8 1.3800(18)
C7 H7 0.9500
C8 N1 1.3744(16)
C8 C9 1.4599(19)
C9 O2 1.2187(16)
C9 O1 1.3405(15)
C10 O1 1.4543(16)
C10 C11 1.5098(19)
C10 H10A 0.9900
C10 H10B 0.9900
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
N1 H1 0.878(17)
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 H1 O2 3_676 0.878(17) 1.977(17) 2.8288(15) 163.0(15)
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
N1 C1 C2 C3 -178.66(14)
C6 C1 C2 C3 -0.1(2)
C1 C2 C3 C4 0.2(2)
C2 C3 C4 C5 -0.5(2)
C2 C3 C4 Cl1 178.63(11)
C3 C4 C5 C6 0.8(2)
Cl1 C4 C5 C6 -178.38(10)
C4 C5 C6 C1 -0.67(19)
C4 C5 C6 C7 178.26(14)
N1 C1 C6 C5 179.20(11)
C2 C1 C6 C5 0.3(2)
N1 C1 C6 C7 0.01(15)
C2 C1 C6 C7 -178.85(12)
C5 C6 C7 C8 -178.65(14)
C1 C6 C7 C8 0.37(15)
C6 C7 C8 N1 -0.63(15)
C6 C7 C8 C9 178.10(13)
N1 C8 C9 O2 -0.4(2)
C7 C8 C9 O2 -178.99(14)
N1 C8 C9 O1 179.38(11)
C7 C8 C9 O1 0.8(2)
C2 C1 N1 C8 178.35(14)
C6 C1 N1 C8 -0.40(15)
C7 C8 N1 C1 0.65(15)
C9 C8 N1 C1 -178.23(12)
O2 C9 O1 C10 0.89(18)
C8 C9 O1 C10 -178.86(11)
C11 C10 O1 C9 -81.73(14)

_cod_database_fobs_code 2241722
