#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:26:02 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180182 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/78/7107861.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_7107861
loop_
_publ_author_name
'Stephen J. Murray'
'Helge Muller-Bunz'
'Hasim Ibrahim'
_publ_section_title
;
 Congested C2-symmetric aryliodanes based on an anti-dimethanoanthracene
 backbone
;
_journal_name_full               Chem.Commun.
_journal_page_first              6268
_journal_paper_doi               10.1039/c2cc32280c
_journal_volume                  48
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H19 I O3'
_chemical_formula_sum            'C16 H19 I O3'
_chemical_formula_weight         386.21
_chemical_name_systematic
;
?
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6625(2)
_cell_length_b                   13.8534(3)
_cell_length_c                   11.4816(2)
_cell_measurement_reflns_used    8675
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.6641
_cell_measurement_theta_min      7.7110
_cell_volume                     1377.85(5)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3196
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12015
_diffrn_reflns_theta_full        75.00
_diffrn_reflns_theta_max         76.87
_diffrn_reflns_theta_min         7.72
_exptl_absorpt_coefficient_mu    18.308
_exptl_absorpt_correction_T_max  0.803
_exptl_absorpt_correction_T_min  0.110
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.862
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.1873
_exptl_crystal_size_mid          0.1514
_exptl_crystal_size_min          0.0115
_refine_diff_density_max         1.044
_refine_diff_density_min         -1.022
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.009(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2570
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0251
_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)+(0.0476P)²+0.4093P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0673
_reflns_number_gt                2449
_reflns_number_total             2570
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c2cc32280c.txt
_cod_data_source_block           has22
_cod_database_code               7107861
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I I 0.108497(19) 0.947035(12) 0.67137(4) 0.01433(9) Uani 1 1 d .
C1 C 0.0504(4) 0.8020(3) 0.6344(3) 0.0161(7) Uani 1 1 d .
C2 C 0.1395(4) 0.7274(3) 0.6797(6) 0.0172(7) Uani 1 1 d .
C3 C 0.2838(4) 0.7239(3) 0.7530(4) 0.0210(8) Uani 1 1 d .
H3 H 0.3522 0.7819 0.7490 0.025 Uiso 1 1 calc R
C4 C 0.2330(5) 0.6917(3) 0.8769(4) 0.0239(8) Uani 1 1 d .
H4A H 0.3204 0.6951 0.9323 0.029 Uiso 1 1 calc R
H4B H 0.1477 0.7326 0.9062 0.029 Uiso 1 1 calc R
C5 C 0.1789(5) 0.5863(3) 0.8596(4) 0.0233(8) Uani 1 1 d .
H5A H 0.0687 0.5787 0.8805 0.028 Uiso 1 1 calc R
H5B H 0.2413 0.5411 0.9070 0.028 Uiso 1 1 calc R
C6 C 0.2050(5) 0.5688(3) 0.7266(4) 0.0191(8) Uani 1 1 d .
H6 H 0.2092 0.4997 0.7013 0.023 Uiso 1 1 calc R
C7 C 0.0908(4) 0.6316(3) 0.6635(6) 0.0166(8) Uani 1 1 d .
C8 C 0.3542(4) 0.6281(3) 0.7079(4) 0.0207(8) Uani 1 1 d .
H8A H 0.3855 0.6315 0.6251 0.025 Uiso 1 1 calc R
H8B H 0.4412 0.6051 0.7564 0.025 Uiso 1 1 calc R
C9 C -0.0455(5) 0.6091(3) 0.6042(3) 0.0197(8) Uani 1 1 d .
H9 H -0.0767 0.5441 0.5929 0.024 Uiso 1 1 calc R
C10 C -0.1334(4) 0.6850(3) 0.5626(4) 0.0164(7) Uani 1 1 d .
C11 C -0.2851(5) 0.6883(3) 0.4974(4) 0.0197(9) Uani 1 1 d .
H11 H -0.3540 0.6312 0.5086 0.024 Uiso 1 1 calc R
C12 C -0.2489(6) 0.7145(3) 0.3701(4) 0.0220(9) Uani 1 1 d .
H12A H -0.3427 0.7106 0.3211 0.026 Uiso 1 1 calc R
H12B H -0.1689 0.6712 0.3374 0.026 Uiso 1 1 calc R
C13 C -0.1890(5) 0.8202(3) 0.3783(4) 0.0204(8) Uani 1 1 d .
H13A H -0.0806 0.8251 0.3517 0.025 Uiso 1 1 calc R
H13B H -0.2538 0.8645 0.3315 0.025 Uiso 1 1 calc R
C14 C -0.2029(4) 0.8427(3) 0.5104(4) 0.0176(7) Uani 1 1 d .
H14 H -0.2038 0.9128 0.5314 0.021 Uiso 1 1 calc R
C15 C -0.3505(5) 0.7862(3) 0.5414(4) 0.0198(8) Uani 1 1 d .
H15A H -0.4420 0.8079 0.4969 0.024 Uiso 1 1 calc R
H15B H -0.3731 0.7861 0.6259 0.024 Uiso 1 1 calc R
C16 C -0.0852(4) 0.7818(3) 0.5735(3) 0.0148(7) Uani 1 1 d .
O1 O 0.3163(3) 0.94578(17) 0.6642(5) 0.0221(6) Uani 1 1 d .
O2 O 0.0795(4) 0.9376(2) 0.8283(3) 0.0222(6) Uani 1 1 d .
O3 O 0.1277(4) 0.9435(2) 0.4444(4) 0.0221(7) Uani 1 1 d D
H1O3 H 0.214(4) 0.943(3) 0.412(5) 0.033 Uiso 1 1 d D
H2O3 H 0.072(6) 0.977(4) 0.399(5) 0.033 Uiso 1 1 d D
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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_site_symmetry_3
O1 I O2 100.5(2) .
O1 I C1 102.67(13) .
O2 I C1 95.58(15) .
O1 I O3 83.7(2) .
O2 I O3 173.27(13) .
C1 I O3 78.29(13) .
O1 I O1 149.87(6) 3_475
O2 I O1 86.87(16) 3_475
C1 I O1 105.66(12) 3_475
O3 I O1 92.09(14) 3_475
C2 C1 C16 120.4(3) .
C2 C1 I 120.0(3) .
C16 C1 I 119.4(3) .
C1 C2 C7 119.1(4) .
C1 C2 C3 133.8(4) .
C7 C2 C3 107.1(4) .
C2 C3 C8 99.6(3) .
C2 C3 C4 106.6(4) .
C8 C3 C4 99.9(3) .
C2 C3 H3 116.1 .
C8 C3 H3 116.1 .
C4 C3 H3 116.1 .
C5 C4 C3 103.8(4) .
C5 C4 H4A 111.0 .
C3 C4 H4A 111.0 .
C5 C4 H4B 111.0 .
C3 C4 H4B 111.0 .
H4A C4 H4B 109.0 .
C4 C5 C6 103.2(3) .
C4 C5 H5A 111.1 .
C6 C5 H5A 111.1 .
C4 C5 H5B 111.1 .
C6 C5 H5B 111.1 .
H5A C5 H5B 109.1 .
C7 C6 C8 100.1(3) .
C7 C6 C5 106.6(4) .
C8 C6 C5 100.0(3) .
C7 C6 H6 115.9 .
C8 C6 H6 115.9 .
C5 C6 H6 115.9 .
C9 C7 C2 121.9(4) .
C9 C7 C6 131.4(4) .
C2 C7 C6 106.5(4) .
C6 C8 C3 94.6(3) .
C6 C8 H8A 112.8 .
C3 C8 H8A 112.8 .
C6 C8 H8B 112.8 .
C3 C8 H8B 112.8 .
H8A C8 H8B 110.3 .
C10 C9 C7 117.7(4) .
C10 C9 H9 121.2 .
C7 C9 H9 121.2 .
C9 C10 C16 122.0(4) .
C9 C10 C11 132.2(4) .
C16 C10 C11 105.8(3) .
C10 C11 C12 107.4(4) .
C10 C11 C15 100.5(3) .
C12 C11 C15 100.2(3) .
C10 C11 H11 115.5 .
C12 C11 H11 115.5 .
C15 C11 H11 115.5 .
C11 C12 C13 103.4(3) .
C11 C12 H12A 111.1 .
C13 C12 H12A 111.1 .
C11 C12 H12B 111.1 .
C13 C12 H12B 111.1 .
H12A C12 H12B 109.0 .
C14 C13 C12 102.9(4) .
C14 C13 H13A 111.2 .
C12 C13 H13A 111.2 .
C14 C13 H13B 111.2 .
C12 C13 H13B 111.2 .
H13A C13 H13B 109.1 .
C16 C14 C15 99.5(3) .
C16 C14 C13 107.7(3) .
C15 C14 C13 100.8(3) .
C16 C14 H14 115.6 .
C15 C14 H14 115.6 .
C13 C14 H14 115.6 .
C14 C15 C11 93.8(3) .
C14 C15 H15A 113.0 .
C11 C15 H15A 113.0 .
C14 C15 H15B 113.0 .
C11 C15 H15B 113.0 .
H15A C15 H15B 110.4 .
C1 C16 C10 118.9(4) .
C1 C16 C14 134.2(4) .
C10 C16 C14 106.8(3) .
I O3 H1O3 120(5) .
I O3 H2O3 125(4) .
H1O3 O3 H2O3 104(6) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I O1 1.802(3) .
I O2 1.824(4) .
I C1 2.114(4) .
I O3 2.612(4) .
I O1 2.936(3) 3_475
C1 C2 1.391(6) .
C1 C16 1.396(6) .
C2 C7 1.405(5) .
C2 C3 1.507(6) .
C3 C8 1.550(6) .
C3 C4 1.554(6) .
C3 H3 1.0000 .
C4 C5 1.547(6) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.562(6) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 C7 1.504(6) .
C6 C8 1.546(5) .
C6 H6 1.0000 .
C7 C9 1.398(6) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.383(6) .
C9 H9 0.9500 .
C10 C16 1.410(6) .
C10 C11 1.513(6) .
C11 C12 1.538(7) .
C11 C15 1.553(6) .
C11 H11 1.0000 .
C12 C13 1.556(6) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.553(5) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C16 1.509(5) .
C14 C15 1.542(5) .
C14 H14 1.0000 .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
O3 H1O3 0.83(2) .
O3 H2O3 0.85(2) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H1O3 O2 0.83(2) 2.03(2) 2.866(5) 177(6) 4_554
O3 H2O3 O2 0.85(2) 1.95(2) 2.777(5) 166(6) 2_574
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
_geom_torsion_site_symmetry_1
O1 I C1 C2 39.4(4) .
O2 I C1 C2 -62.7(4) .
O3 I C1 C2 120.1(4) .
O1 I C1 C2 -151.0(4) 3_475
O1 I C1 C16 -146.5(3) .
O2 I C1 C16 111.4(3) .
O3 I C1 C16 -65.8(3) .
O1 I C1 C16 23.1(3) 3_475
C16 C1 C2 C7 -0.1(7) .
I C1 C2 C7 174.0(4) .
C16 C1 C2 C3 -176.4(5) .
I C1 C2 C3 -2.3(8) .
C1 C2 C3 C8 -149.7(6) .
C7 C2 C3 C8 33.7(5) .
C1 C2 C3 C4 106.9(6) .
C7 C2 C3 C4 -69.7(5) .
C2 C3 C4 C5 67.2(4) .
C8 C3 C4 C5 -36.0(4) .
C3 C4 C5 C6 0.2(4) .
C4 C5 C6 C7 -67.9(4) .
C4 C5 C6 C8 35.9(4) .
C1 C2 C7 C9 -0.7(8) .
C3 C2 C7 C9 176.5(5) .
C1 C2 C7 C6 -177.2(5) .
C3 C2 C7 C6 -0.1(6) .
C8 C6 C7 C9 150.2(6) .
C5 C6 C7 C9 -106.1(6) .
C8 C6 C7 C2 -33.8(5) .
C5 C6 C7 C2 70.0(5) .
C7 C6 C8 C3 51.7(4) .
C5 C6 C8 C3 -57.3(4) .
C2 C3 C8 C6 -51.5(4) .
C4 C3 C8 C6 57.4(4) .
C2 C7 C9 C10 -0.8(8) .
C6 C7 C9 C10 174.8(5) .
C7 C9 C10 C16 3.1(7) .
C7 C9 C10 C11 -179.0(5) .
C9 C10 C11 C12 -106.0(5) .
C16 C10 C11 C12 72.2(4) .
C9 C10 C11 C15 149.7(5) .
C16 C10 C11 C15 -32.2(4) .
C10 C11 C12 C13 -67.1(4) .
C15 C11 C12 C13 37.4(4) .
C11 C12 C13 C14 -1.6(4) .
C12 C13 C14 C16 68.5(4) .
C12 C13 C14 C15 -35.2(4) .
C16 C14 C15 C11 -53.2(3) .
C13 C14 C15 C11 57.0(3) .
C10 C11 C15 C14 52.1(4) .
C12 C11 C15 C14 -58.0(3) .
C2 C1 C16 C10 2.3(6) .
I C1 C16 C10 -171.8(3) .
C2 C1 C16 C14 -177.1(5) .
I C1 C16 C14 8.8(6) .
C9 C10 C16 C1 -3.9(6) .
C11 C10 C16 C1 177.7(4) .
C9 C10 C16 C14 175.6(4) .
C11 C10 C16 C14 -2.7(4) .
C15 C14 C16 C1 -143.7(5) .
C13 C14 C16 C1 111.6(5) .
C15 C14 C16 C10 36.8(4) .
C13 C14 C16 C10 -67.9(4) .
