#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/02/2210289.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_2210289
loop_
_publ_author_name
'Butcher, Ray J.'
'Yathirajan, H. S.'
'Ashalatha, B. V.'
'Narayana, B.'
'Sarojini, B. K.'
_publ_section_title
;
 Methyl 5-chloro-1H-indole-2-carboxylate
;
_journal_coeditor_code           HK2103
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3915
_journal_page_last               o3917
_journal_paper_doi               10.1107/S1600536806032181
_journal_volume                  62
_journal_year                    2006
_chemical_formula_moiety         'C10 H8 Cl N O2'
_chemical_formula_sum            'C10 H8 Cl N O2'
_chemical_formula_weight         209.62
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 103.932(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.786(2)
_cell_length_b                   4.0070(7)
_cell_length_c                   19.040(3)
_cell_measurement_reflns_used    3123
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.08
_cell_measurement_theta_min      2.19
_cell_volume                     946.8(3)
_computing_cell_refinement       Apex2
_computing_data_collection       'Apex2 (Bruker 2006)'
_computing_data_reduction        Apex2
_computing_molecular_graphics    'SHELXTL (Bruker 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
'Bruker Apex2 CCD area-detector diffractometer'
_diffrn_measurement_method       'φ and ω 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  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8678
_diffrn_reflns_theta_full        28.23
_diffrn_reflns_theta_max         28.23
_diffrn_reflns_theta_min         1.74
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_T_max  0.9393
_exptl_absorpt_correction_T_min  0.7777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.71
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.283
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2321
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0559P)²+0.2468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1179
_reflns_number_gt                1674
_reflns_number_total             2321
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2103.cif
_cod_data_source_block           I
_cod_original_cell_volume        946.7(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2210289
_cod_database_fobs_code          2210289
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
Cl Cl 0.56243(4) 0.46838(15) 0.11140(3) 0.0720(2) Uani d . 1
O O1 0.37073(10) 0.8089(4) 0.50232(7) 0.0651(4) Uani d . 1
O O2 0.23939(10) 0.5069(3) 0.43190(7) 0.0567(3) Uani d . 1
N N1 0.48357(10) 0.7992(4) 0.39161(7) 0.0457(3) Uani d . 1
H H1A 0.5199 0.9033 0.4291 0.055 Uiso calc R 1
C C2 0.38397(12) 0.6551(4) 0.38495(8) 0.0424(4) Uani d . 1
C C3 0.35050(12) 0.5122(4) 0.31811(9) 0.0444(4) Uani d . 1
H H3A 0.2861 0.3989 0.3003 0.053 Uiso calc R 1
C C9 0.43280(12) 0.5697(4) 0.28113(8) 0.0413(3) Uani d . 1
C C4 0.44607(13) 0.4837(4) 0.21214(9) 0.0477(4) Uani d . 1
H H4A 0.3932 0.3664 0.1793 0.057 Uiso calc R 1
C C5 0.53987(13) 0.5792(5) 0.19517(9) 0.0493(4) Uani d . 1
C C6 0.62071(13) 0.7604(5) 0.24288(10) 0.0525(4) Uani d . 1
H H6A 0.6825 0.8229 0.2285 0.063 Uiso calc R 1
C C7 0.60965(13) 0.8461(5) 0.31024(10) 0.0516(4) Uani d . 1
H H7A 0.6632 0.9642 0.3424 0.062 Uiso calc R 1
C C8 0.51485(11) 0.7495(4) 0.32900(8) 0.0418(4) Uani d . 1
C C10 0.33332(12) 0.6692(4) 0.44568(8) 0.0455(4) Uani d . 1
C C11 0.18660(18) 0.4908(6) 0.49082(12) 0.0691(6) Uani d . 1
H H11A 0.1178 0.3840 0.4746 0.104 Uiso calc R 1
H H11B 0.1766 0.7126 0.5071 0.104 Uiso calc R 1
H H11C 0.2303 0.3651 0.5300 0.104 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl 0.0790(4) 0.0839(4) 0.0630(3) 0.0040(3) 0.0368(3) -0.0052(2)
O1 0.0569(7) 0.0895(11) 0.0486(7) -0.0128(7) 0.0118(6) -0.0167(7)
O2 0.0536(7) 0.0675(9) 0.0517(7) -0.0136(6) 0.0179(5) -0.0060(6)
N1 0.0389(6) 0.0516(9) 0.0433(6) -0.0011(6) 0.0039(5) -0.0047(6)
C2 0.0382(7) 0.0430(9) 0.0438(8) 0.0016(6) 0.0057(6) 0.0006(7)
C3 0.0400(7) 0.0461(10) 0.0462(8) -0.0024(6) 0.0086(6) -0.0023(7)
C9 0.0383(7) 0.0399(8) 0.0441(8) 0.0020(6) 0.0066(6) 0.0007(6)
C4 0.0470(8) 0.0484(10) 0.0466(8) 0.0001(7) 0.0093(7) -0.0034(7)
C5 0.0523(9) 0.0497(10) 0.0493(9) 0.0092(8) 0.0187(7) 0.0040(8)
C6 0.0411(8) 0.0525(11) 0.0660(10) 0.0044(7) 0.0171(7) 0.0073(9)
C7 0.0378(7) 0.0529(10) 0.0618(10) -0.0015(7) 0.0075(7) 0.0010(8)
C8 0.0371(7) 0.0408(9) 0.0453(8) 0.0034(6) 0.0053(6) 0.0010(7)
C10 0.0429(8) 0.0481(10) 0.0432(8) 0.0026(7) 0.0059(6) 0.0005(7)
C11 0.0680(12) 0.0805(16) 0.0680(12) -0.0119(11) 0.0343(10) -0.0029(10)
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
C10 O2 C11 115.86(14)
C8 N1 C2 108.58(13)
C8 N1 H1A 125.7
C2 N1 H1A 125.7
C3 C2 N1 109.70(14)
C3 C2 C10 131.00(15)
N1 C2 C10 119.29(14)
C2 C3 C9 106.89(14)
C2 C3 H3A 126.6
C9 C3 H3A 126.6
C4 C9 C8 119.34(14)
C4 C9 C3 133.95(15)
C8 C9 C3 106.71(13)
C5 C4 C9 117.45(16)
C5 C4 H4A 121.3
C9 C4 H4A 121.3
C4 C5 C6 122.84(16)
C4 C5 Cl 119.42(14)
C6 C5 Cl 117.73(13)
C7 C6 C5 120.71(15)
C7 C6 H6A 119.6
C5 C6 H6A 119.6
C6 C7 C8 117.50(16)
C6 C7 H7A 121.3
C8 C7 H7A 121.3
N1 C8 C7 129.73(15)
N1 C8 C9 108.12(13)
C7 C8 C9 122.15(15)
O1 C10 O2 123.06(16)
O1 C10 C2 124.83(16)
O2 C10 C2 112.10(14)
O2 C11 H11A 109.5
O2 C11 H11B 109.5
H11A C11 H11B 109.5
O2 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl C5 1.7452(17)
O1 C10 1.207(2)
O2 C10 1.335(2)
O2 C11 1.443(2)
N1 C8 1.360(2)
N1 C2 1.376(2)
N1 H1A 0.8600
C2 C3 1.367(2)
C2 C10 1.456(2)
C3 C9 1.419(2)
C3 H3A 0.9300
C9 C4 1.407(2)
C9 C8 1.411(2)
C4 C5 1.370(2)
C4 H4A 0.9300
C5 C6 1.403(3)
C6 C7 1.368(2)
C6 H6A 0.9300
C7 C8 1.398(2)
C7 H7A 0.9300
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 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
N1 H1A O1 3_676 0.86 2.03 2.8641(19) 164.1 yes
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
C8 N1 C2 C3 -0.05(19)
C8 N1 C2 C10 178.95(14)
N1 C2 C3 C9 -0.08(19)
C10 C2 C3 C9 -178.93(17)
C2 C3 C9 C4 179.37(18)
C2 C3 C9 C8 0.18(18)
C8 C9 C4 C5 0.4(2)
C3 C9 C4 C5 -178.70(17)
C9 C4 C5 C6 -1.0(3)
C9 C4 C5 Cl 178.08(12)
C4 C5 C6 C7 1.1(3)
Cl C5 C6 C7 -177.93(14)
C5 C6 C7 C8 -0.7(3)
C2 N1 C8 C7 -179.32(17)
C2 N1 C8 C9 0.17(18)
C6 C7 C8 N1 179.56(16)
C6 C7 C8 C9 0.1(3)
C4 C9 C8 N1 -179.55(14)
C3 C9 C8 N1 -0.21(18)
C4 C9 C8 C7 0.0(2)
C3 C9 C8 C7 179.32(16)
C11 O2 C10 O1 -3.4(3)
C11 O2 C10 C2 176.40(15)
C3 C2 C10 O1 -178.88(19)
N1 C2 C10 O1 2.4(3)
C3 C2 C10 O2 1.3(3)
N1 C2 C10 O2 -177.42(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3964356
