#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/69/2236939.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_2236939
loop_
_publ_author_name
'Yokota, Ruri'
'Kitamura, Chitoshi'
'Kawase, Takeshi'
_publ_section_title
;
 9,10-Diiodophenanthrene
;
_journal_coeditor_code           JJ2155
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3323
_journal_paper_doi               10.1107/S1600536812045758
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C14 H8 I2'
_chemical_formula_moiety         'C14 H8 I2'
_chemical_formula_sum            'C14 H8 I2'
_chemical_formula_weight         430
_chemical_name_systematic
;
9,10-diiodophenanthrene
;
_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
_cell_angle_alpha                90
_cell_angle_beta                 111.953(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.094(2)
_cell_length_b                   9.4557(14)
_cell_length_c                   7.4187(10)
_cell_measurement_reflns_used    3465
_cell_measurement_temperature    223
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      3.045
_cell_volume                     1177.2(3)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1999)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      223
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5595
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.49
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.309
_exptl_absorpt_correction_T_max  0.8688
_exptl_absorpt_correction_T_min  0.3877
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(NUMABS; Higashi, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.92
_refine_diff_density_min         -0.92
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1345
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0077P)²+13.1956P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0664
_refine_ls_wR_factor_ref         0.083
_reflns_number_gt                1077
_reflns_number_total             1345
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jj2155.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2236939
_cod_database_fobs_code          2236939
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_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
C C1 0.3399(3) 0.4417(6) 0.4793(7) 0.0368(12) Uani d . 1 1
H H1 0.3127 0.3564 0.4332 0.044 Uiso calc R 1 1
C C2 0.3020(3) 0.5667(8) 0.4155(8) 0.0470(15) Uani d . 1 1
H H2 0.2488 0.5669 0.3275 0.056 Uiso calc R 1 1
C C3 0.3408(3) 0.6927(7) 0.4781(9) 0.0467(15) Uani d . 1 1
H H3 0.3146 0.7786 0.4306 0.056 Uiso calc R 1 1
C C4 0.4171(4) 0.6931(6) 0.6089(8) 0.0424(13) Uani d . 1 1
H H4 0.4426 0.78 0.6529 0.051 Uiso calc R 1 1
C C5 0.4587(3) 0.5675(5) 0.6798(7) 0.0289(10) Uani d . 1 1
C C6 0.4192(3) 0.4383(5) 0.6137(7) 0.0261(9) Uani d . 1 1
C C7 0.4618(3) 0.3079(5) 0.6846(7) 0.0281(10) Uani d . 1 1
I I1 0.40244(3) 0.11933(4) 0.58098(7) 0.05783(18) 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
C1 0.029(2) 0.051(3) 0.029(3) 0.003(2) 0.008(2) 0.001(2)
C2 0.026(3) 0.078(4) 0.034(3) 0.012(3) 0.007(2) 0.010(3)
C3 0.038(3) 0.057(4) 0.048(3) 0.024(3) 0.019(3) 0.020(3)
C4 0.048(3) 0.040(3) 0.048(3) 0.012(2) 0.028(3) 0.008(3)
C5 0.030(2) 0.030(2) 0.031(3) 0.0021(19) 0.017(2) 0.0012(19)
C6 0.023(2) 0.035(2) 0.024(2) 0.0010(18) 0.0126(18) 0.0001(18)
C7 0.033(2) 0.026(2) 0.025(2) -0.0029(18) 0.010(2) -0.0020(18)
I1 0.0670(3) 0.0402(2) 0.0526(3) -0.01527(19) 0.0067(2) -0.00726(18)
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 0 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2 C1 C6 . . 120.9(5)
C2 C1 H1 . . 119.6
C6 C1 H1 . . 119.6
C1 C2 C3 . . 120.7(5)
C1 C2 H2 . . 119.7
C3 C2 H2 . . 119.7
C4 C3 C2 . . 119.9(5)
C4 C3 H3 . . 120.1
C2 C3 H3 . . 120.1
C3 C4 C5 . . 121.8(6)
C3 C4 H4 . . 119.1
C5 C4 H4 . . 119.1
C4 C5 C6 . . 118.2(5)
C4 C5 C5 . 2_656 121.9(3)
C6 C5 C5 . 2_656 119.8(3)
C5 C6 C1 . . 118.5(5)
C5 C6 C7 . . 118.7(4)
C1 C6 C7 . . 122.8(5)
C7 C7 C6 2_656 . 121.5(3)
C7 C7 I1 2_656 . 120.77(13)
C6 C7 I1 . . 117.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.359(8)
C1 C6 . 1.409(7)
C1 H1 . 0.94
C2 C3 . 1.372(9)
C2 H2 . 0.94
C3 C4 . 1.359(8)
C3 H3 . 0.94
C4 C5 . 1.399(7)
C4 H4 . 0.94
C5 C6 . 1.408(7)
C5 C5 2_656 1.467(10)
C6 C7 . 1.445(6)
C7 C7 2_656 1.360(9)
C7 I1 . 2.075(5)
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C6 C1 C2 C3 . . 1.1(8)
C1 C2 C3 C4 . . -1.6(9)
C2 C3 C4 C5 . . 1.4(9)
C3 C4 C5 C6 . . -0.7(8)
C3 C4 C5 C5 . 2_656 179.7(6)
C4 C5 C6 C1 . . 0.2(7)
C5 C5 C6 C1 2_656 . 179.8(5)
C4 C5 C6 C7 . . 179.5(5)
C5 C5 C6 C7 2_656 . -0.9(8)
C2 C1 C6 C5 . . -0.4(7)
C2 C1 C6 C7 . . -179.6(5)
C5 C6 C7 C7 . 2_656 1.2(8)
C1 C6 C7 C7 . 2_656 -179.6(6)
C5 C6 C7 I1 . . -179.0(3)
C1 C6 C7 I1 . . 0.2(6)
