#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/31/2013126.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_2013126
loop_
_publ_author_name
'Merz, Klaus'
_publ_section_title
;
 Secondary interactions in 1-iodo-3-nitrobenzene and
 1-iodo-3,5-dinitrobenzene
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o65
_journal_page_last               o67
_journal_paper_doi               10.1107/S0108270102023041
_journal_volume                  59
_journal_year                    2003
_chemical_formula_moiety         'C6 H3 I1 N2 O4'
_chemical_formula_sum            'C6 H3 I N2 O4'
_chemical_formula_weight         294.00
_chemical_name_common            3-Iodo-5-dinitro-benzene
_chemical_name_systematic
;
3-iodo-1,5-dinitro-benzene
;
_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
_cell_angle_alpha                90
_cell_angle_beta                 101.766(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.842(9)
_cell_length_b                   8.164(5)
_cell_length_c                   15.288(9)
_cell_measurement_reflns_used    53
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      17.6
_cell_measurement_theta_min      3.4
_cell_volume                     1691.3(18)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL and ORTEPIII (Farrugia, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Siemens, 1996)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker SMART 1000 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  0.042
_diffrn_reflns_av_sigmaI/netI    0.061
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6318
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_min         2.91
_diffrn_standards_decay_%        0.1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.770
_exptl_absorpt_correction_T_max  0.470
_exptl_absorpt_correction_T_min  0.421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '[SADABS (Sheldrick, 1996; Blessing, 1995)]'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.93
_refine_diff_density_min         -0.99
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2404
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.052
_refine_ls_R_factor_gt           0.037
_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)+(0.0103P)²+2.3695P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.080
_refine_ls_wR_factor_ref         0.084
_reflns_number_gt                1927
_reflns_number_total             2404
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn1017.cif
_cod_data_source_block           III
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1691.2(18)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C6 H3 I1 N2 O4'
_cod_database_code               2013126
_cod_database_fobs_code          2013126
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
I1 0.100566(19) 0.80925(3) 0.380331(14) 0.03627(11) Uani d . 1 . . I
O1 0.1019(3) 0.6800(4) 0.80264(19) 0.0559(9) Uani d . 1 . . O
C1 0.1186(3) 0.6743(4) 0.6559(2) 0.0287(7) Uani d . 1 . . C
C2 0.1089(3) 0.7634(4) 0.5773(2) 0.0270(7) Uani d . 1 . . C
H2A 0.0980 0.8771 0.5763 0.032 Uiso calc R 1 . . H
C3 0.1158(3) 0.6784(4) 0.5002(2) 0.0259(7) Uani d . 1 . . C
N1 0.1096(3) 0.7627(5) 0.7376(2) 0.0435(9) Uani d . 1 . . N
C6 0.1357(3) 0.5090(5) 0.6610(2) 0.0304(8) Uani d . 1 . . C
H6A 0.1422 0.4513 0.7151 0.036 Uiso calc R 1 . . H
O3 0.1861(3) 0.1901(4) 0.6581(3) 0.0648(11) Uani d . 1 . . O
C4 0.1326(3) 0.5120(5) 0.5017(2) 0.0295(7) Uani d . 1 . . C
H4A 0.1370 0.4547 0.4493 0.035 Uiso calc R 1 . . H
O2 0.1094(4) 0.9105(5) 0.7352(2) 0.0717(12) Uani d . 1 . . O
N2 0.1617(3) 0.2547(5) 0.5853(3) 0.0412(8) Uani d . 1 . . N
C5 0.1427(3) 0.4324(4) 0.5828(2) 0.0294(7) Uani d . 1 . . C
O4 0.1494(4) 0.1813(4) 0.5149(3) 0.0734(13) Uani d . 1 . . O
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
I1 0.04522(17) 0.04186(17) 0.02156(12) -0.00267(12) 0.00645(10) 0.00836(9)
O1 0.070(2) 0.077(3) 0.0245(13) 0.0093(19) 0.0184(14) 0.0080(13)
C1 0.0337(18) 0.035(2) 0.0190(14) -0.0019(16) 0.0084(13) -0.0003(12)
C2 0.0361(19) 0.0202(16) 0.0265(15) -0.0005(15) 0.0110(14) 0.0029(12)
C3 0.0287(16) 0.0291(18) 0.0202(14) -0.0019(15) 0.0057(12) 0.0030(12)
N1 0.060(2) 0.052(2) 0.0208(14) 0.001(2) 0.0134(15) -0.0031(14)
C6 0.0321(18) 0.0319(19) 0.0276(16) -0.0008(16) 0.0069(14) 0.0098(13)
O3 0.083(3) 0.0376(19) 0.070(2) 0.0053(19) 0.006(2) 0.0210(15)
C4 0.0335(18) 0.0285(18) 0.0272(16) -0.0010(16) 0.0078(13) -0.0034(13)
O2 0.133(4) 0.044(2) 0.0466(18) -0.009(2) 0.040(2) -0.0178(15)
N2 0.0399(19) 0.0253(16) 0.058(2) 0.0007(16) 0.0086(16) 0.0019(16)
C5 0.0307(17) 0.0238(17) 0.0325(17) -0.0018(16) 0.0038(13) 0.0058(13)
O4 0.118(4) 0.0310(18) 0.069(3) 0.008(2) 0.014(2) -0.0094(15)
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'
I I -0.4742 1.8119 '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
C6 C1 C2 123.5(3) ?
C6 C1 N1 118.6(3) yes
C2 C1 N1 117.9(3) yes
C1 C2 C3 117.5(3) ?
C1 C2 H2A 121.3 ?
C3 C2 H2A 121.3 ?
C4 C3 C2 121.3(3) ?
C4 C3 I1 120.3(2) yes
C2 C3 I1 118.4(3) yes
O2 N1 O1 125.1(4) yes
O2 N1 C1 117.8(3) yes
O1 N1 C1 117.1(4) yes
C1 C6 C5 116.2(3) ?
C1 C6 H6A 121.9 ?
C5 C6 H6A 121.9 ?
C3 C4 C5 117.7(3) ?
C3 C4 H4A 121.2 ?
C5 C4 H4A 121.2 ?
O4 N2 O3 124.1(4) yes
O4 N2 C5 118.1(4) yes
O3 N2 C5 117.7(4) yes
C6 C5 C4 123.8(3) ?
C6 C5 N2 118.1(3) yes
C4 C5 N2 118.1(3) yes
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
I1 C3 . 2.094(3) yes
O1 N1 . 1.225(5) yes
C1 C6 . 1.370(5) ?
C1 C2 . 1.388(5) ?
C1 N1 . 1.470(5) yes
C2 C3 . 1.388(5) ?
C2 H2A . 0.9400 ?
C3 C4 . 1.377(5) ?
N1 O2 . 1.207(6) yes
C6 C5 . 1.370(5) ?
C6 H6A . 0.9400 ?
O3 N2 . 1.215(5) yes
C4 C5 . 1.383(5) ?
C4 H4A . 0.9400 ?
N2 O4 . 1.213(5) yes
N2 C5 . 1.473(5) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 205244
