#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/18/2211876.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_2211876
loop_
_publ_author_name
'Kolandaivelu Saminathan'
'Kandasamy Sivakumar'
_publ_section_title
;
 Indole--picric acid (1/1)
;
_journal_coeditor_code           LH2191
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o236
_journal_page_last               o238
_journal_paper_doi               10.1107/S1600536806052512
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C8 H7 N, C6 H3 N3 O7'
_chemical_formula_moiety         'C8 H7 N, C6 H3 N3 O7'
_chemical_formula_sum            'C14 H10 N4 O7'
_chemical_formula_weight         346.26
_chemical_name_systematic
;
Indole--picric acid (1/1)
;
_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                 94.912(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4586(19)
_cell_length_b                   6.723(3)
_cell_length_c                   16.158(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      15
_cell_volume                     1456.6(8)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω--2θ
_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  0.0153
_diffrn_reflns_av_sigmaI/netI    0.0670
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            2659
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.53
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 100
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.9999
_exptl_absorpt_correction_T_min  0.9888
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.236
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         2546
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.909
_refine_ls_R_factor_all          0.1928
_refine_ls_R_factor_gt           0.0692
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1531P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2123
_refine_ls_wR_factor_ref         0.2711
_reflns_number_gt                816
_reflns_number_total             2546
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2191.cif
_cod_data_source_block           I
_cod_original_cell_volume        1456.7(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2211876
_cod_database_fobs_code          2211876
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_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
O O2 0.9954(3) 0.6384(8) 0.3538(3) 0.132(2) Uani d . 1 . .
O O3 0.9088(3) 0.5860(8) 0.2402(3) 0.1146(17) Uani d . 1 . .
O O4 0.5585(4) 0.5859(12) 0.2248(4) 0.187(3) Uani d . 1 . .
O O5 0.4805(4) 0.6338(11) 0.3266(4) 0.180(3) Uani d . 1 . .
O O6 0.6683(7) 0.6280(10) 0.6028(4) 0.186(4) Uani d . 1 . .
O O7 0.8263(6) 0.6326(9) 0.6088(3) 0.164(3) Uani d . 1 . .
N N1 0.9188(4) 0.6158(7) 0.3144(3) 0.0759(12) Uani d . 1 . .
N N2 0.5562(4) 0.6100(9) 0.2968(4) 0.0960(17) Uani d . 1 . .
N N3 0.7418(8) 0.6266(9) 0.5726(3) 0.119(2) Uani d . 1 . .
C C1 0.8306(3) 0.6201(7) 0.4414(3) 0.0608(13) Uani d D 1 . .
H H5' 0.8919 0.6209 0.4727 0.073 Uiso calc PR 0.50 A 1
O O1 0.9103(5) 0.6204(14) 0.4914(5) 0.0961(17) Uani d PD 0.50 B 2
H H1 0.9593 0.6254 0.4646 0.144 Uiso calc PR 0.50 B 2
C C2 0.8259(3) 0.6157(7) 0.3572(3) 0.0512(11) Uani d . 1 B .
C C3 0.7366(3) 0.6136(6) 0.3097(3) 0.0515(11) Uani d . 1 . .
H H3 0.7349 0.6108 0.2520 0.062 Uiso calc R 1 B .
C C4 0.6500(3) 0.6158(7) 0.3481(3) 0.0536(11) Uani d . 1 B .
C C5 0.6509(4) 0.6177(8) 0.4336(4) 0.0698(15) Uani d D 1 . .
H H5 0.5921 0.6154 0.4599 0.084 Uiso calc PR 0.50 B 1
O O1' 0.5742(5) 0.6155(15) 0.4771(5) 0.0961(17) Uani d PD 0.50 B 2
H H1' 0.5932 0.6105 0.5266 0.144 Uiso calc PR 0.50 B 2
C C6 0.7447(5) 0.6233(7) 0.4791(3) 0.0664(14) Uani d . 1 B .
N N4 0.2733(4) 0.6127(6) 0.1969(3) 0.0819(14) Uani d . 1 . .
H H4 0.3211 0.6082 0.2357 0.098 Uiso calc R 1 . .
C C7 0.1746(5) 0.6148(9) 0.2074(4) 0.0861(17) Uani d . 1 . .
H H7 0.1496 0.6126 0.2593 0.103 Uiso calc R 1 . .
C C8 0.1178(5) 0.6204(8) 0.1379(4) 0.0781(16) Uani d . 1 . .
H H8 0.0485 0.6226 0.1312 0.094 Uiso calc R 1 . .
C C9 0.1872(4) 0.6226(7) 0.0726(4) 0.0733(15) Uani d . 1 . .
C C10 0.1728(6) 0.6264(8) -0.0118(5) 0.110(3) Uani d . 1 . .
H H10 0.1094 0.6302 -0.0397 0.132 Uiso calc R 1 . .
C C11 0.2606(8) 0.6241(10) -0.0542(4) 0.100(2) Uani d . 1 . .
H H11 0.2541 0.6246 -0.1120 0.120 Uiso calc R 1 . .
C C12 0.3545(6) 0.6212(9) -0.0144(4) 0.094(2) Uani d . 1 . .
H H12 0.4095 0.6213 -0.0456 0.113 Uiso calc R 1 . .
C C13 0.3690(4) 0.6181(7) 0.0700(4) 0.0744(15) Uani d . 1 . .
H H13 0.4324 0.6156 0.0978 0.089 Uiso calc R 1 . .
C C14 0.2836(3) 0.6189(7) 0.1114(3) 0.0541(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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 N1 O3 125.2(5)
O2 N1 C2 119.0(5)
O3 N1 C2 115.7(5)
O5 N2 O4 121.4(6)
O5 N2 C4 120.3(7)
O4 N2 C4 118.3(6)
O6 N3 O7 126.5(8)
O6 N3 C6 121.6(9)
O7 N3 C6 111.9(8)
O1 C1 C6 114.6(6)
O1 C1 C2 126.5(6)
C6 C1 C2 118.9(4)
C6 C1 H5' 120.5
C2 C1 H5' 120.5
C1 O1 H1 109.5
C1 C2 C3 121.7(4)
C1 C2 N1 119.9(4)
C3 C2 N1 118.3(4)
C4 C3 C2 119.1(4)
C4 C3 H3 120.4
C2 C3 H3 120.4
C3 C4 C5 121.4(4)
C3 C4 N2 118.3(5)
C5 C4 N2 120.3(5)
O1' C5 C4 127.1(6)
O1' C5 C6 115.9(6)
C4 C5 C6 117.0(5)
C4 C5 H5 121.5
C6 C5 H5 121.5
C5 O1' H1' 109.5
C1 C6 C5 121.8(4)
C1 C6 N3 123.0(6)
C5 C6 N3 115.1(6)
C7 N4 C14 107.8(5)
C7 N4 H4 126.1
C14 N4 H4 126.1
C8 C7 N4 113.7(6)
C8 C7 H7 123.2
N4 C7 H7 123.2
C7 C8 C9 104.9(5)
C7 C8 H8 127.6
C9 C8 H8 127.6
C10 C9 C14 120.0(6)
C10 C9 C8 132.4(6)
C14 C9 C8 107.6(5)
C9 C10 C11 115.6(6)
C9 C10 H10 122.2
C11 C10 H10 122.2
C12 C11 C10 123.2(6)
C12 C11 H11 118.4
C10 C11 H11 118.4
C13 C12 C11 121.3(6)
C13 C12 H12 119.4
C11 C12 H12 119.4
C12 C13 C14 115.6(5)
C12 C13 H13 122.2
C14 C13 H13 122.2
C13 C14 C9 124.4(5)
C13 C14 N4 129.5(5)
C9 C14 N4 106.1(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O2 N1 1.174(5) ?
O3 N1 1.211(6) ?
O4 N2 1.178(7) ?
O5 N2 1.175(7) ?
O6 N3 1.141(10) ?
O7 N3 1.234(9) ?
N1 C2 1.480(6) y
N2 C4 1.450(6) y
N3 C6 1.514(7) y
C1 O1 1.286(7) y
C1 C6 1.353(7) ?
C1 C2 1.358(6) ?
C1 H5' 0.9300 ?
O1 H1 0.8200 ?
C2 C3 1.369(6) ?
C3 C4 1.367(6) ?
C3 H3 0.9300 ?
C4 C5 1.380(7) ?
C5 O1' 1.298(7) y
C5 C6 1.406(7) ?
C5 H5 0.9300 ?
O1' H1' 0.8200 ?
N4 C7 1.353(7) y
N4 C14 1.400(6) y
N4 H4 0.8600 ?
C7 C8 1.303(8) ?
C7 H7 0.9300 ?
C8 C9 1.468(7) ?
C8 H8 0.9300 ?
C9 C10 1.361(8) ?
C9 C14 1.392(7) ?
C10 C11 1.417(10) ?
C10 H10 0.9300 ?
C11 C12 1.369(9) ?
C11 H11 0.9300 ?
C12 C13 1.360(8) ?
C12 H12 0.9300 ?
C13 C14 1.379(6) ?
C13 H13 0.9300 ?
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
N4 H4 O5 . 0.86 2.50 3.346(7) 167.7
C13 H13 O4 . 0.93 2.56 3.423(8) 155.3
C7 H7 O2 1_455 0.93 2.69 3.524(8) 150.2
C8 H8 O3 1_455 0.93 2.70 3.391(7) 132.1
O1 H1 O2 . 0.82 1.90 2.590(6) 142
O1' H1' O6 . 0.82 1.53 2.302(6) 156
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
O1 C1 C2 C3 179.3(7)
C6 C1 C2 C3 -0.3(8)
O1 C1 C2 N1 -1.6(10)
C6 C1 C2 N1 178.9(5)
O2 N1 C2 C1 -7.0(8)
O3 N1 C2 C1 170.9(5)
O2 N1 C2 C3 172.1(6)
O3 N1 C2 C3 -10.0(8)
C1 C2 C3 C4 -0.1(7)
N1 C2 C3 C4 -179.2(4)
C2 C3 C4 C5 -0.8(7)
C2 C3 C4 N2 -178.9(5)
O5 N2 C4 C3 -171.6(7)
O4 N2 C4 C3 6.6(9)
O5 N2 C4 C5 10.3(10)
O4 N2 C4 C5 -171.6(7)
C3 C4 C5 O1' -178.4(7)
N2 C4 C5 O1' -0.3(11)
C3 C4 C5 C6 1.9(8)
N2 C4 C5 C6 180.0(5)
O1 C1 C6 C5 -178.1(7)
C2 C1 C6 C5 1.5(8)
O1 C1 C6 N3 -0.1(9)
C2 C1 C6 N3 179.5(5)
O1' C5 C6 C1 178.0(8)
C4 C5 C6 C1 -2.2(8)
O1' C5 C6 N3 -0.2(8)
C4 C5 C6 N3 179.6(5)
O6 N3 C6 C1 -179.5(7)
O7 N3 C6 C1 2.3(9)
O6 N3 C6 C5 -1.4(10)
O7 N3 C6 C5 -179.6(6)
C14 N4 C7 C8 0.5(7)
N4 C7 C8 C9 -0.1(7)
C7 C8 C9 C10 179.4(6)
C7 C8 C9 C14 -0.3(6)
C14 C9 C10 C11 0.6(8)
C8 C9 C10 C11 -179.0(6)
C9 C10 C11 C12 -0.9(10)
C10 C11 C12 C13 0.7(11)
C11 C12 C13 C14 -0.2(9)
C12 C13 C14 C9 0.0(8)
C12 C13 C14 N4 178.7(5)
C10 C9 C14 C13 -0.2(8)
C8 C9 C14 C13 179.5(5)
C10 C9 C14 N4 -179.1(5)
C8 C9 C14 N4 0.6(6)
C7 N4 C14 C13 -179.5(5)
C7 N4 C14 C9 -0.6(6)
