#------------------------------------------------------------------------------
#$Date: 2016-03-04 13:46:30 +0200 (Fri, 04 Mar 2016) $
#$Revision: 177490 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/25/1542512.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1542512
loop_
_publ_author_name
'Golen, James A.'
'Manke, David R.'
_publ_section_title
;
 4-Iodo-1H-indole-2,3-dione
;
_journal_coeditor_code           SU4013
_journal_issue                   2
_journal_name_full               IUCrData
_journal_page_first              x160215
_journal_paper_doi               10.1107/S2414314616002157
_journal_volume                  1
_journal_year                    2016
_chemical_formula_iupac          'C8 H4 I N O2'
_chemical_formula_moiety         'C8 H4 I N O2'
_chemical_formula_sum            'C8 H4 I N O2'
_chemical_formula_weight         273.02
_chemical_name_systematic
;
4-Iodo-1H-indole-2,3-dione
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 91.249(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6138(9)
_cell_length_b                   13.9658(17)
_cell_length_c                   7.3866(10)
_cell_measurement_reflns_used    7683
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.73
_cell_measurement_theta_min      2.92
_cell_volume                     785.25(17)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009) and Mercury (Macrae et
al.,  2008)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009) and publCIF (Westrip,
2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      297.68
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16058
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         25.742
_diffrn_reflns_theta_min         2.917
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.029
_exptl_absorpt_correction_T_max  0.2594
_exptl_absorpt_correction_T_min  0.1815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.309
_exptl_crystal_description       rod
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.950
_refine_diff_density_min         -0.834
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1491
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.192
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0260P)²+3.7223P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0819
_reflns_number_gt                1268
_reflns_number_total             1491
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su4013sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 1542512.cif.'
_cod_database_code               1542512
_cod_database_fobs_code          1542512
_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.
;
_shelx_estimated_absorpt_t_min   0.432
_shelx_estimated_absorpt_t_max   0.739
loop_
_space_group_symop_operation_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_occupancy
I I1 0.76809(5) 0.52256(3) 0.58699(6) 0.03698(15) Uani d 1
O O1 1.1415(6) 0.8920(3) 0.4389(7) 0.0440(11) Uani d 1
O O2 1.0723(6) 0.6869(3) 0.4540(7) 0.0438(11) Uani d 1
N N1 0.8656(7) 0.8997(3) 0.5598(7) 0.0349(11) Uani d 1
H H1 0.854(9) 0.9613(16) 0.561(9) 0.042 Uiso d 1
C C1 1.0079(8) 0.8563(4) 0.4961(8) 0.0334(13) Uani d 1
C C2 0.9695(7) 0.7460(4) 0.5078(7) 0.0284(12) Uani d 1
C C3 0.7944(7) 0.7395(4) 0.5841(7) 0.0242(11) Uani d 1
C C4 0.6850(7) 0.6629(4) 0.6254(7) 0.0265(11) Uani d 1
C C5 0.5197(7) 0.6816(4) 0.6915(8) 0.0320(13) Uani d 1
H H5 0.4451 0.6315 0.7211 0.038 Uiso calc 1
C C6 0.4664(8) 0.7758(5) 0.7130(8) 0.0369(14) Uani d 1
H H6 0.3549 0.7873 0.7571 0.044 Uiso calc 1
C C7 0.5710(8) 0.8532(4) 0.6722(8) 0.0350(13) Uani d 1
H H7 0.5316 0.9157 0.6859 0.042 Uiso calc 1
C C8 0.7365(7) 0.8335(4) 0.6102(7) 0.0268(12) 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'
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
C1 N1 H1 123(5)
C1 N1 C8 111.8(5)
C8 N1 H1 125(5)
O1 C1 N1 128.8(6)
O1 C1 C2 125.4(5)
N1 C1 C2 105.8(5)
O2 C2 C1 121.9(5)
O2 C2 C3 133.3(5)
C3 C2 C1 104.8(4)
C4 C3 C2 133.4(5)
C4 C3 C8 119.9(5)
C8 C3 C2 106.7(5)
C3 C4 I1 120.5(4)
C5 C4 I1 120.5(4)
C5 C4 C3 119.0(5)
C4 C5 H5 120.3
C4 C5 C6 119.3(5)
C6 C5 H5 120.3
C5 C6 H6 118.4
C7 C6 C5 123.1(6)
C7 C6 H6 118.4
C6 C7 H7 121.6
C8 C7 C6 116.9(5)
C8 C7 H7 121.6
C3 C8 N1 110.9(5)
C7 C8 N1 127.3(5)
C7 C8 C3 121.8(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C4 2.081(5)
O1 C1 1.216(7)
O2 C2 1.211(7)
N1 H1 0.87(2)
N1 C1 1.336(8)
N1 C8 1.406(7)
C1 C2 1.571(8)
C2 C3 1.462(7)
C3 C4 1.393(8)
C3 C8 1.399(8)
C4 C5 1.385(8)
C5 H5 0.9300
C5 C6 1.386(9)
C6 H6 0.9300
C6 C7 1.380(9)
C7 H7 0.9300
C7 C8 1.378(8)
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 O1 3_776 0.87(2) 2.05(2) 2.910(6) 173(7)
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
I1 C4 C5 C6 -179.0(4)
O1 C1 C2 O2 -2.2(10)
O1 C1 C2 C3 -179.8(6)
O2 C2 C3 C4 1.6(11)
O2 C2 C3 C8 -176.3(7)
N1 C1 C2 O2 177.5(6)
N1 C1 C2 C3 -0.1(6)
C1 N1 C8 C3 1.5(7)
C1 N1 C8 C7 -176.5(6)
C1 C2 C3 C4 178.8(6)
C1 C2 C3 C8 1.0(6)
C2 C3 C4 I1 2.2(8)
C2 C3 C4 C5 -177.4(6)
C2 C3 C8 N1 -1.5(6)
C2 C3 C8 C7 176.6(5)
C3 C4 C5 C6 0.7(8)
C4 C3 C8 N1 -179.7(5)
C4 C3 C8 C7 -1.6(8)
C4 C5 C6 C7 -0.2(9)
C5 C6 C7 C8 -1.1(9)
C6 C7 C8 N1 179.8(6)
C6 C7 C8 C3 2.0(8)
C8 N1 C1 O1 178.9(6)
C8 N1 C1 C2 -0.8(7)
C8 C3 C4 I1 179.8(4)
C8 C3 C4 C5 0.2(8)
