#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/81/2238114.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_2238114
loop_
_publ_author_name
'Förster, Sebastian'
'Seichter, Wilhelm'
'Weber, Edwin'
_publ_section_title
;
 1,3-Diiodoazulene-2-carbonitrile
;
_journal_coeditor_code           ZP2002
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o654
_journal_page_last               o655
_journal_paper_doi               10.1107/S1600536813008301
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C11 H5 I2 N'
_chemical_formula_moiety         'C11 H5 I2 N'
_chemical_formula_sum            'C11 H5 I2 N'
_chemical_formula_weight         404.96
_chemical_name_systematic
;
1,3-Diiodoazulene-2-carbonitrile
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.9520(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.26770(10)
_cell_length_b                   14.9344(4)
_cell_length_c                   16.7882(4)
_cell_measurement_reflns_used    7883
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.47
_cell_measurement_theta_min      2.73
_cell_volume                     1062.14(5)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'ORTEP-3 for Windows  (Farrugia, 2012)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'phi and omega 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  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17691
_diffrn_reflns_theta_full        35.10
_diffrn_reflns_theta_max         35.10
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    5.878
_exptl_absorpt_correction_T_max  0.8434
_exptl_absorpt_correction_T_min  0.1500
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    2.532
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.479
_refine_diff_density_min         -1.324
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         4616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0237
_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)+(0.0289P)²+0.3529P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0554
_refine_ls_wR_factor_ref         0.0580
_reflns_number_gt                3863
_reflns_number_total             4616
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            zp2002.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2238114
_cod_database_fobs_code          2238114
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
_atom_site_symmetry_multiplicity
I I1 0.78365(3) 0.118650(8) 0.153674(8) 0.01453(4) Uani d . 1 1
I I2 0.54859(3) 0.379652(8) 0.426773(8) 0.01708(4) Uani d . 1 1
N N1 1.0480(4) 0.14850(13) 0.39516(11) 0.0216(4) Uani d . 1 1
C C1 0.6331(4) 0.23056(12) 0.21157(11) 0.0131(3) Uani d . 1 1
C C2 0.7006(4) 0.24765(12) 0.29426(11) 0.0129(3) Uani d . 1 1
C C3 0.5399(4) 0.32630(12) 0.31275(11) 0.0131(3) Uani d . 1 1
C C4 0.3685(4) 0.35906(12) 0.24230(11) 0.0126(3) Uani d . 1 1
C C10 0.4300(4) 0.29734(12) 0.17661(11) 0.0126(3) Uani d . 1 1
C C9 0.3126(5) 0.30350(13) 0.09587(12) 0.0157(3) Uani d . 1 1
H H9 0.3852 0.2591 0.0620 0.019 Uiso calc R 1 1
C C8 0.1030(5) 0.36596(14) 0.05796(12) 0.0182(4) Uani d . 1 1
H H8 0.0509 0.3581 0.0018 0.022 Uiso calc R 1 1
C C7 -0.0398(5) 0.43785(14) 0.09082(13) 0.0186(4) Uani d . 1 1
H H7 -0.1803 0.4714 0.0540 0.022 Uiso calc R 1 1
C C6 -0.0090(5) 0.46858(13) 0.16964(13) 0.0178(4) Uani d . 1 1
H H6 -0.1279 0.5206 0.1788 0.021 Uiso calc R 1 1
C C5 0.1722(4) 0.43354(12) 0.23683(12) 0.0148(3) Uani d . 1 1
H H5 0.1601 0.4648 0.2856 0.018 Uiso calc R 1 1
C C11 0.8938(5) 0.19344(13) 0.35015(12) 0.0151(3) Uani d . 1 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
I1 0.01660(6) 0.01155(6) 0.01611(6) 0.00045(4) 0.00466(4) -0.00113(4)
I2 0.02230(7) 0.01668(6) 0.01229(6) 0.00117(4) 0.00219(4) -0.00198(4)
N1 0.0239(9) 0.0197(8) 0.0198(9) 0.0022(7) -0.0036(7) 0.0007(7)
C1 0.0144(7) 0.0101(7) 0.0152(8) -0.0011(6) 0.0029(6) -0.0011(6)
C2 0.0131(7) 0.0110(7) 0.0145(8) -0.0006(6) 0.0020(6) 0.0001(6)
C3 0.0150(8) 0.0117(7) 0.0127(8) -0.0010(6) 0.0022(6) -0.0011(6)
C4 0.0131(7) 0.0113(7) 0.0136(8) -0.0022(6) 0.0027(6) -0.0001(6)
C10 0.0137(7) 0.0109(7) 0.0134(8) -0.0013(6) 0.0026(6) -0.0001(6)
C9 0.0177(8) 0.0147(8) 0.0146(8) -0.0023(6) 0.0017(6) -0.0003(6)
C8 0.0200(9) 0.0204(9) 0.0133(8) -0.0017(7) -0.0008(7) 0.0031(7)
C7 0.0161(8) 0.0212(9) 0.0181(9) 0.0006(7) 0.0004(7) 0.0067(7)
C6 0.0168(8) 0.0132(8) 0.0234(10) 0.0024(6) 0.0026(7) 0.0033(7)
C5 0.0156(8) 0.0116(7) 0.0178(9) 0.0002(6) 0.0044(7) -0.0001(6)
C11 0.0161(8) 0.0129(8) 0.0162(8) -0.0009(6) 0.0017(6) -0.0019(6)
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'
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
C10 C1 C2 109.05(16)
C10 C1 I1 125.99(14)
C2 C1 I1 124.80(13)
C1 C2 C3 108.70(16)
C1 C2 C11 125.46(17)
C3 C2 C11 125.83(17)
C4 C3 C2 108.81(16)
C4 C3 I2 126.53(14)
C2 C3 I2 124.62(13)
C5 C4 C3 125.77(18)
C5 C4 C10 127.40(17)
C3 C4 C10 106.80(16)
C9 C10 C1 125.92(18)
C9 C10 C4 127.44(17)
C1 C10 C4 106.64(16)
C10 C9 C8 128.76(19)
C10 C9 H9 115.6
C8 C9 H9 115.6
C7 C8 C9 128.91(19)
C7 C8 H8 115.5
C9 C8 H8 115.5
C8 C7 C6 129.82(19)
C8 C7 H7 115.1
C6 C7 H7 115.1
C5 C6 C7 128.80(19)
C5 C6 H6 115.6
C7 C6 H6 115.6
C4 C5 C6 128.82(19)
C4 C5 H5 115.6
C6 C5 H5 115.6
N1 C11 C2 179.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C1 2.0741(18)
I2 C3 2.0697(19)
N1 C11 1.155(3)
C1 C10 1.403(3)
C1 C2 1.407(3)
C2 C3 1.413(3)
C2 C11 1.424(3)
C3 C4 1.401(3)
C4 C5 1.389(3)
C4 C10 1.485(3)
C10 C9 1.390(3)
C9 C8 1.392(3)
C9 H9 0.9500
C8 C7 1.382(3)
C8 H8 0.9500
C7 C6 1.392(3)
C7 H7 0.9500
C6 C5 1.390(3)
C6 H6 0.9500
C5 H5 0.9500
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
C8 H8 N1 4_465 0.95 2.62 3.400(3) 139.1
C6 H6 Cg(C11---N1) 4_465 0.95 2.76 3.63(3) 152.1
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
C10 C1 C2 C3 -0.1(2)
I1 C1 C2 C3 -175.66(13)
C10 C1 C2 C11 178.71(18)
I1 C1 C2 C11 3.2(3)
C1 C2 C3 C4 0.4(2)
C11 C2 C3 C4 -178.40(18)
C1 C2 C3 I2 178.31(13)
C11 C2 C3 I2 -0.5(3)
C2 C3 C4 C5 177.63(18)
I2 C3 C4 C5 -0.2(3)
C2 C3 C4 C10 -0.5(2)
I2 C3 C4 C10 -178.39(13)
C2 C1 C10 C9 179.57(18)
I1 C1 C10 C9 -4.9(3)
C2 C1 C10 C4 -0.2(2)
I1 C1 C10 C4 175.27(13)
C5 C4 C10 C9 2.5(3)
C3 C4 C10 C9 -179.32(18)
C5 C4 C10 C1 -177.67(18)
C3 C4 C10 C1 0.5(2)
C1 C10 C9 C8 177.6(2)
C4 C10 C9 C8 -2.6(3)
C10 C9 C8 C7 0.4(4)
C9 C8 C7 C6 1.5(4)
C8 C7 C6 C5 -1.1(4)
C3 C4 C5 C6 -178.5(2)
C10 C4 C5 C6 -0.8(3)
C7 C6 C5 C4 0.1(4)
C1 C2 C11 N1 -55(15)
C3 C2 C11 N1 123(15)
