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#$Date: 2024-10-06 12:16:49 +0300 (Sun, 06 Oct 2024) $
#$Revision: 295331 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/00/7160097.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_7160097
loop_
_publ_author_name
'Al-Zoubi, Raed M'
'Al-Jammal, Walid K'
'Shkoor, Mohanad'
'Bani-Yaseen, Abdulilah D'
'Khan, Abbas'
'Agouni, Abdelali'
'McDonald, Robert'
_publ_section_title
;
 Efficient and regioselective synthesis of ortho-diiodinated
 homobenzylic alcohol derivatives: in silico evaluation as
 potential anticancer IDO/TDO inhibitors.
;
_journal_issue                   36
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7395
_journal_page_last               7410
_journal_paper_doi               10.1039/d4ob01076k
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C11 H14 I2 O2'
_chemical_formula_sum            'C11 H14 I2 O2'
_chemical_formula_weight         432.02
_chemical_name_systematic
1-(2,6-diiodo-4-methylphenyl)-3-methoxypropan-2-ol
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2024-06-21 deposited with the CCDC.	2024-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.2020(5)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   19.9273(8)
_cell_length_b                   8.4314(3)
_cell_length_c                   33.0097(13)
_cell_measurement_reflns_used    9803
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.85
_cell_measurement_theta_min      2.49
_cell_volume                     5298.0(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            48427
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.332
_diffrn_reflns_theta_min         1.292
_exptl_absorpt_coefficient_mu    4.729
_exptl_absorpt_correction_T_max  0.6964
_exptl_absorpt_correction_T_min  0.3616
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.167
_exptl_crystal_description       fragment
_exptl_crystal_F_000             3232
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexanes and dichloromethane'
_exptl_crystal_size_max          0.318
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.113
_refine_diff_density_max         0.798
_refine_diff_density_min         -1.050
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     561
_refine_ls_number_reflns         13041
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0246
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0269P)²+3.2851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0564
_refine_ls_wR_factor_ref         0.0592
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11132
_reflns_number_total             13041
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01076k2.cif
_cod_data_source_block           jus1619
_cod_depositor_comments
'Adding full bibliography for 7160097--7160098.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7160097
_shelx_shelxl_version_number     2014/7
_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   0.315
_shelx_estimated_absorpt_t_max   0.617
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_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1A I 0.13147(2) 0.31000(3) 0.00139(2) 0.03884(5) Uani 1 1 d . . . . .
I2A I 0.02734(2) -0.03393(3) 0.13643(2) 0.03985(6) Uani 1 1 d . . . . .
O1A O 0.23704(11) 0.1923(3) 0.15605(7) 0.0363(5) Uani 1 1 d . . . . .
H1OA H 0.2467(19) 0.242(4) 0.1767(11) 0.043(11) Uiso 1 1 d . . . . .
O2A O 0.18646(11) 0.5179(2) 0.14993(6) 0.0314(4) Uani 1 1 d . . . . .
C1A C 0.14615(14) 0.1240(3) 0.09479(8) 0.0271(6) Uani 1 1 d . . . . .
H1A H 0.1782 0.1329 0.0770 0.033 Uiso 1 1 calc R U . . .
H1B H 0.1516 0.0159 0.1071 0.033 Uiso 1 1 calc R U . . .
C2A C 0.16904(14) 0.2439(3) 0.13101(8) 0.0271(6) Uani 1 1 d . . . . .
H2A H 0.1358 0.2394 0.1485 0.032 Uiso 1 1 calc R U . . .
C3A C 0.17104(14) 0.4105(3) 0.11491(8) 0.0272(6) Uani 1 1 d . . . . .
H3A H 0.2075 0.4189 0.1001 0.033 Uiso 1 1 calc R U . . .
H3B H 0.1251 0.4376 0.0945 0.033 Uiso 1 1 calc R U . . .
C4A C 0.07134(14) 0.1427(3) 0.06648(8) 0.0256(6) Uani 1 1 d . . . . .
C5A C 0.05390(15) 0.2173(3) 0.02672(8) 0.0273(6) Uani 1 1 d . . . . .
C6A C -0.01509(15) 0.2354(4) 0.00138(9) 0.0313(6) Uani 1 1 d . . . . .
H6A H -0.0243 0.2870 -0.0253 0.038 Uiso 1 1 calc R U . . .
C7A C -0.07089(15) 0.1786(3) 0.01469(9) 0.0293(6) Uani 1 1 d . . . . .
C8A C -0.05540(15) 0.1019(3) 0.05326(9) 0.0307(6) Uani 1 1 d . . . . .
H8A H -0.0923 0.0595 0.0627 0.037 Uiso 1 1 calc R U . . .
C9A C 0.01406(15) 0.0861(3) 0.07847(8) 0.0268(6) Uani 1 1 d . . . . .
C10A C -0.14618(16) 0.1969(4) -0.01230(10) 0.0412(8) Uani 1 1 d . . . . .
H10A H -0.1775 0.1524 0.0027 0.049 Uiso 1 1 calc R U . . .
H10B H -0.1531 0.1405 -0.0392 0.049 Uiso 1 1 calc R U . . .
H10C H -0.1568 0.3096 -0.0180 0.049 Uiso 1 1 calc R U . . .
C11A C 0.18541(19) 0.6774(4) 0.13557(11) 0.0443(8) Uani 1 1 d . . . . .
H11A H 0.1961 0.7494 0.1600 0.053 Uiso 1 1 calc R U . . .
H11B H 0.2207 0.6905 0.1205 0.053 Uiso 1 1 calc R U . . .
H11C H 0.1388 0.7021 0.1164 0.053 Uiso 1 1 calc R U . . .
I1B I 0.38848(2) 0.54103(3) 0.38479(2) 0.03626(5) Uani 1 1 d . . . . .
I2B I 0.47347(2) 0.17131(2) 0.24723(2) 0.03291(5) Uani 1 1 d . . . . .
O1B O 0.27477(11) 0.4060(3) 0.22605(6) 0.0296(4) Uani 1 1 d . . . . .
H1OB H 0.2605(19) 0.465(4) 0.2093(11) 0.045(11) Uiso 1 1 d . . . . .
O2B O 0.30744(11) 0.7255(2) 0.22782(6) 0.0333(5) Uani 1 1 d . . . . .
C1B C 0.36352(13) 0.3521(3) 0.29051(8) 0.0250(5) Uani 1 1 d . . . . .
H1C H 0.3334 0.3689 0.3092 0.030 Uiso 1 1 calc R U . . .
H1D H 0.3566 0.2416 0.2800 0.030 Uiso 1 1 calc R U . . .
C2B C 0.34024(14) 0.4657(3) 0.25272(8) 0.0241(5) Uani 1 1 d . . . . .
H2B H 0.3757 0.4638 0.2367 0.029 Uiso 1 1 calc R U . . .
C3B C 0.33112(15) 0.6343(3) 0.26571(8) 0.0274(6) Uani 1 1 d . . . . .
H3C H 0.2962 0.6384 0.2817 0.033 Uiso 1 1 calc R U . . .
H3D H 0.3763 0.6764 0.2840 0.033 Uiso 1 1 calc R U . . .
C4B C 0.43927(13) 0.3740(3) 0.31607(8) 0.0233(5) Uani 1 1 d . . . . .
C5B C 0.46116(14) 0.4548(3) 0.35473(8) 0.0246(5) Uani 1 1 d . . . . .
C6B C 0.53140(15) 0.4811(3) 0.37680(8) 0.0283(6) Uani 1 1 d . . . . .
H6B H 0.5434 0.5394 0.4026 0.034 Uiso 1 1 calc R U . . .
C7B C 0.58379(14) 0.4225(3) 0.36121(8) 0.0259(6) Uani 1 1 d . . . . .
C8B C 0.56485(14) 0.3370(3) 0.32360(8) 0.0265(6) Uani 1 1 d . . . . .
H8B H 0.6000 0.2943 0.3126 0.032 Uiso 1 1 calc R U . . .
C9B C 0.49422(14) 0.3140(3) 0.30203(8) 0.0230(5) Uani 1 1 d . . . . .
C10B C 0.66084(15) 0.4493(4) 0.38475(10) 0.0378(7) Uani 1 1 d . . . . .
H10D H 0.6657 0.5450 0.4022 0.045 Uiso 1 1 calc R U . . .
H10E H 0.6873 0.4623 0.3643 0.045 Uiso 1 1 calc R U . . .
H10F H 0.6791 0.3577 0.4030 0.045 Uiso 1 1 calc R U . . .
C11B C 0.29863(18) 0.8879(4) 0.23608(11) 0.0406(7) Uani 1 1 d . . . . .
H11D H 0.2823 0.9458 0.2092 0.049 Uiso 1 1 calc R U . . .
H11E H 0.2638 0.8983 0.2516 0.049 Uiso 1 1 calc R U . . .
H11F H 0.3436 0.9321 0.2532 0.049 Uiso 1 1 calc R U . . .
I1C I 0.15514(2) 0.26110(2) 0.25370(2) 0.03148(5) Uani 1 1 d . . . . .
I2C I 0.02430(2) -0.04087(2) 0.38174(2) 0.03538(5) Uani 1 1 d . . . . .
O1C O 0.23834(12) 0.1627(3) 0.40966(7) 0.0388(5) Uani 1 1 d . . . . .
H1OC H 0.253(2) 0.217(5) 0.4266(12) 0.057(13) Uiso 1 1 d . . . . .
O2C O 0.19837(12) 0.4836(2) 0.40391(6) 0.0377(5) Uani 1 1 d . . . . .
C1C C 0.15222(13) 0.0965(3) 0.34600(8) 0.0233(5) Uani 1 1 d . . . . .
H1E H 0.1873 0.0989 0.3301 0.028 Uiso 1 1 calc R U . . .
H1F H 0.1534 -0.0106 0.3585 0.028 Uiso 1 1 calc R U . . .
C2C C 0.17309(15) 0.2186(3) 0.38195(8) 0.0293(6) Uani 1 1 d . . . . .
H2C H 0.1371 0.2182 0.3976 0.035 Uiso 1 1 calc R U . . .
C3C C 0.18038(15) 0.3848(3) 0.36710(9) 0.0318(6) Uani 1 1 d . . . . .
H3E H 0.2176 0.3892 0.3528 0.038 Uiso 1 1 calc R U . . .
H3F H 0.1356 0.4204 0.3468 0.038 Uiso 1 1 calc R U . . .
C4C C 0.08040(13) 0.1248(3) 0.31557(8) 0.0221(5) Uani 1 1 d . . . . .
C5C C 0.06954(14) 0.1972(3) 0.27590(8) 0.0246(5) Uani 1 1 d . . . . .
C6C C 0.00338(15) 0.2319(3) 0.24931(9) 0.0299(6) Uani 1 1 d . . . . .
H6C H -0.0013 0.2804 0.2226 0.036 Uiso 1 1 calc R U . . .
C7C C -0.05642(15) 0.1966(3) 0.26112(9) 0.0302(6) Uani 1 1 d . . . . .
C8C C -0.04773(14) 0.1198(3) 0.29948(9) 0.0277(6) Uani 1 1 d . . . . .
H8C H -0.0878 0.0911 0.3079 0.033 Uiso 1 1 calc R U . . .
C9C C 0.01900(14) 0.0845(3) 0.32568(8) 0.0241(5) Uani 1 1 d . . . . .
C10C C -0.12837(16) 0.2390(4) 0.23303(11) 0.0455(8) Uani 1 1 d . . . . .
H10G H -0.1605 0.1502 0.2321 0.055 Uiso 1 1 calc R U . . .
H10H H -0.1261 0.2615 0.2043 0.055 Uiso 1 1 calc R U . . .
H10I H -0.1455 0.3331 0.2444 0.055 Uiso 1 1 calc R U . . .
C11C C 0.19881(19) 0.6458(4) 0.39327(11) 0.0429(8) Uani 1 1 d . . . . .
H11G H 0.2113 0.7097 0.4192 0.052 Uiso 1 1 calc R U . . .
H11H H 0.2333 0.6635 0.3779 0.052 Uiso 1 1 calc R U . . .
H11I H 0.1521 0.6767 0.3753 0.052 Uiso 1 1 calc R U . . .
I1D I 0.37374(2) 0.08056(3) 0.63409(2) 0.03588(5) Uani 1 1 d . . . . .
I2D I 0.47517(2) -0.26087(2) 0.49809(2) 0.03929(6) Uani 1 1 d . . . . .
O1D O 0.26487(12) -0.0389(3) 0.48073(8) 0.0405(5) Uani 1 1 d . . . . .
H1OD H 0.254(2) 0.005(5) 0.4597(12) 0.056(13) Uiso 1 1 d . . . . .
O2D O 0.31751(11) 0.2836(2) 0.48436(6) 0.0337(5) Uani 1 1 d . . . . .
C1D C 0.35821(15) -0.1071(3) 0.54122(9) 0.0290(6) Uani 1 1 d . . . . .
H1G H 0.3268 -0.0981 0.5594 0.035 Uiso 1 1 calc R U . . .
H1H H 0.3534 -0.2160 0.5295 0.035 Uiso 1 1 calc R U . . .
C2D C 0.33379(15) 0.0106(3) 0.50450(9) 0.0281(6) Uani 1 1 d . . . . .
H2D H 0.3656 0.0026 0.4861 0.034 Uiso 1 1 calc R U . . .
C3D C 0.33416(15) 0.1796(3) 0.51993(8) 0.0283(6) Uani 1 1 d . . . . .
H3G H 0.2992 0.1917 0.5357 0.034 Uiso 1 1 calc R U . . .
H3H H 0.3811 0.2061 0.5393 0.034 Uiso 1 1 calc R U . . .
C4D C 0.43310(14) -0.0831(3) 0.56834(8) 0.0263(6) Uani 1 1 d . . . . .
C5D C 0.45118(15) -0.0057(3) 0.60763(9) 0.0282(6) Uani 1 1 d . . . . .
C6D C 0.52017(16) 0.0207(4) 0.63178(9) 0.0323(6) Uani 1 1 d . . . . .
H6D H 0.5297 0.0749 0.6581 0.039 Uiso 1 1 calc R U . . .
C7D C 0.57542(15) -0.0320(3) 0.61752(9) 0.0318(6) Uani 1 1 d . . . . .
C8D C 0.55980(15) -0.1133(3) 0.57940(9) 0.0311(6) Uani 1 1 d . . . . .
H8D H 0.5967 -0.1533 0.5696 0.037 Uiso 1 1 calc R U . . .
C9D C 0.49038(15) -0.1366(3) 0.55545(9) 0.0289(6) Uani 1 1 d . . . . .
C10D C 0.65110(17) -0.0056(4) 0.64304(10) 0.0442(8) Uani 1 1 d . . . . .
H10J H 0.6814 -0.0204 0.6247 0.053 Uiso 1 1 calc R U . . .
H10K H 0.6642 -0.0818 0.6665 0.053 Uiso 1 1 calc R U . . .
H10L H 0.6567 0.1025 0.6544 0.053 Uiso 1 1 calc R U . . .
C11D C 0.31891(19) 0.4447(4) 0.49690(10) 0.0445(8) Uani 1 1 d . . . . .
H11J H 0.3072 0.5127 0.4717 0.053 Uiso 1 1 calc R U . . .
H11K H 0.2845 0.4614 0.5124 0.053 Uiso 1 1 calc R U . . .
H11L H 0.3660 0.4714 0.5152 0.053 Uiso 1 1 calc R U . . .
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11A O2A C3A 110.5(2) . . ?
C4A C1A C2A 115.2(2) . . ?
O1A C2A C3A 111.6(2) . . ?
O1A C2A C1A 105.3(2) . . ?
C3A C2A C1A 112.0(2) . . ?
O2A C3A C2A 109.1(2) . . ?
C9A C4A C5A 114.9(2) . . ?
C9A C4A C1A 121.8(2) . . ?
C5A C4A C1A 123.3(2) . . ?
C6A C5A C4A 122.6(3) . . ?
C6A C5A I1A 115.5(2) . . ?
C4A C5A I1A 121.9(2) . . ?
C5A C6A C7A 120.7(3) . . ?
C8A C7A C6A 118.0(3) . . ?
C8A C7A C10A 120.3(3) . . ?
C6A C7A C10A 121.6(3) . . ?
C7A C8A C9A 120.5(3) . . ?
C8A C9A C4A 123.2(3) . . ?
C8A C9A I2A 115.0(2) . . ?
C4A C9A I2A 121.7(2) . . ?
C11B O2B C3B 112.4(2) . . ?
C4B C1B C2B 113.0(2) . . ?
O1B C2B C3B 109.9(2) . . ?
O1B C2B C1B 106.4(2) . . ?
C3B C2B C1B 112.9(2) . . ?
O2B C3B C2B 107.2(2) . . ?
C5B C4B C9B 114.4(2) . . ?
C5B C4B C1B 124.2(2) . . ?
C9B C4B C1B 121.4(2) . . ?
C6B C5B C4B 123.4(2) . . ?
C6B C5B I1B 114.98(19) . . ?
C4B C5B I1B 121.63(19) . . ?
C7B C6B C5B 120.0(3) . . ?
C6B C7B C8B 118.8(2) . . ?
C6B C7B C10B 121.1(3) . . ?
C8B C7B C10B 120.1(2) . . ?
C7B C8B C9B 119.8(2) . . ?
C8B C9B C4B 123.4(2) . . ?
C8B C9B I2B 115.52(19) . . ?
C4B C9B I2B 120.98(19) . . ?
C11C O2C C3C 111.8(2) . . ?
C4C C1C C2C 113.4(2) . . ?
O1C C2C C3C 111.0(2) . . ?
O1C C2C C1C 105.1(2) . . ?
C3C C2C C1C 113.8(2) . . ?
O2C C3C C2C 106.9(2) . . ?
C9C C4C C5C 115.0(2) . . ?
C9C C4C C1C 121.8(2) . . ?
C5C C4C C1C 123.1(2) . . ?
C6C C5C C4C 122.7(2) . . ?
C6C C5C I1C 116.2(2) . . ?
C4C C5C I1C 121.11(19) . . ?
C5C C6C C7C 120.8(3) . . ?
C8C C7C C6C 118.0(3) . . ?
C8C C7C C10C 120.9(3) . . ?
C6C C7C C10C 121.1(3) . . ?
C9C C8C C7C 120.5(3) . . ?
C8C C9C C4C 122.9(2) . . ?
C8C C9C I2C 116.41(19) . . ?
C4C C9C I2C 120.68(19) . . ?
C11D O2D C3D 111.7(2) . . ?
C4D C1D C2D 114.2(2) . . ?
O1D C2D C3D 111.6(2) . . ?
O1D C2D C1D 105.9(2) . . ?
C3D C2D C1D 112.0(2) . . ?
O2D C3D C2D 109.0(2) . . ?
C5D C4D C9D 114.9(3) . . ?
C5D C4D C1D 123.4(2) . . ?
C9D C4D C1D 121.8(3) . . ?
C6D C5D C4D 123.1(3) . . ?
C6D C5D I1D 115.3(2) . . ?
C4D C5D I1D 121.6(2) . . ?
C5D C6D C7D 120.2(3) . . ?
C8D C7D C6D 118.5(3) . . ?
C8D C7D C10D 119.9(3) . . ?
C6D C7D C10D 121.6(3) . . ?
C7D C8D C9D 120.4(3) . . ?
C8D C9D C4D 122.9(3) . . ?
C8D C9D I2D 115.9(2) . . ?
C4D C9D I2D 121.2(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1A C5A 2.113(3) . ?
I2A C9A 2.111(3) . ?
O1A C2A 1.430(3) . ?
O2A C11A 1.424(4) . ?
O2A C3A 1.428(3) . ?
C1A C4A 1.515(4) . ?
C1A C2A 1.529(4) . ?
C2A C3A 1.507(4) . ?
C4A C9A 1.398(4) . ?
C4A C5A 1.403(4) . ?
C5A C6A 1.390(4) . ?
C6A C7A 1.396(4) . ?
C7A C8A 1.379(4) . ?
C7A C10A 1.509(4) . ?
C8A C9A 1.395(4) . ?
I1B C5B 2.112(3) . ?
I2B C9B 2.109(3) . ?
O1B C2B 1.432(3) . ?
O2B C11B 1.417(4) . ?
O2B C3B 1.425(3) . ?
C1B C4B 1.507(4) . ?
C1B C2B 1.532(4) . ?
C2B C3B 1.511(4) . ?
C4B C5B 1.397(4) . ?
C4B C9B 1.404(3) . ?
C5B C6B 1.391(4) . ?
C6B C7B 1.385(4) . ?
C7B C8B 1.388(4) . ?
C7B C10B 1.519(4) . ?
C8B C9B 1.390(4) . ?
I1C C5C 2.116(3) . ?
I2C C9C 2.107(3) . ?
O1C C2C 1.430(3) . ?
O2C C11C 1.413(4) . ?
O2C C3C 1.429(3) . ?
C1C C4C 1.505(3) . ?
C1C C2C 1.533(4) . ?
C2C C3C 1.505(4) . ?
C4C C9C 1.402(3) . ?
C4C C5C 1.402(3) . ?
C5C C6C 1.382(4) . ?
C6C C7C 1.391(4) . ?
C7C C8C 1.387(4) . ?
C7C C10C 1.502(4) . ?
C8C C9C 1.387(4) . ?
I1D C5D 2.114(3) . ?
I2D C9D 2.106(3) . ?
O1D C2D 1.428(4) . ?
O2D C11D 1.418(4) . ?
O2D C3D 1.424(3) . ?
C1D C4D 1.510(4) . ?
C1D C2D 1.531(4) . ?
C2D C3D 1.513(4) . ?
C4D C5D 1.401(4) . ?
C4D C9D 1.405(4) . ?
C5D C6D 1.388(4) . ?
C6D C7D 1.392(4) . ?
C7D C8D 1.385(4) . ?
C7D C10D 1.511(4) . ?
C8D C9D 1.389(4) . ?
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
O1A H1OA O1B 0.78(3) 2.08(4) 2.850(3) 171(4) .
O1B H1OB O2A 0.74(4) 2.12(4) 2.772(3) 147(4) .
O1C H1OC O2D 0.71(4) 2.04(4) 2.703(3) 155(4) .
O1D H1OD O1C 0.76(4) 2.07(4) 2.818(3) 168(4) .
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4A C1A C2A O1A 173.2(2) . . . . ?
C4A C1A C2A C3A -65.4(3) . . . . ?
C11A O2A C3A C2A -177.2(2) . . . . ?
O1A C2A C3A O2A -67.5(3) . . . . ?
C1A C2A C3A O2A 174.8(2) . . . . ?
C2A C1A C4A C9A -79.5(3) . . . . ?
C2A C1A C4A C5A 100.3(3) . . . . ?
C9A C4A C5A C6A 0.8(4) . . . . ?
C1A C4A C5A C6A -179.1(3) . . . . ?
C9A C4A C5A I1A -179.25(19) . . . . ?
C1A C4A C5A I1A 0.9(4) . . . . ?
C4A C5A C6A C7A -0.2(4) . . . . ?
I1A C5A C6A C7A 179.9(2) . . . . ?
C5A C6A C7A C8A -1.1(4) . . . . ?
C5A C6A C7A C10A -180.0(3) . . . . ?
C6A C7A C8A C9A 1.7(4) . . . . ?
C10A C7A C8A C9A -179.4(3) . . . . ?
C7A C8A C9A C4A -1.1(4) . . . . ?
C7A C8A C9A I2A 179.8(2) . . . . ?
C5A C4A C9A C8A -0.1(4) . . . . ?
C1A C4A C9A C8A 179.7(3) . . . . ?
C5A C4A C9A I2A 178.92(19) . . . . ?
C1A C4A C9A I2A -1.2(4) . . . . ?
C4B C1B C2B O1B 165.9(2) . . . . ?
C4B C1B C2B C3B -73.4(3) . . . . ?
C11B O2B C3B C2B -178.5(2) . . . . ?
O1B C2B C3B O2B -59.5(3) . . . . ?
C1B C2B C3B O2B -178.2(2) . . . . ?
C2B C1B C4B C5B 101.9(3) . . . . ?
C2B C1B C4B C9B -77.6(3) . . . . ?
C9B C4B C5B C6B 3.0(4) . . . . ?
C1B C4B C5B C6B -176.5(3) . . . . ?
C9B C4B C5B I1B -175.32(18) . . . . ?
C1B C4B C5B I1B 5.2(4) . . . . ?
C4B C5B C6B C7B -1.8(4) . . . . ?
I1B C5B C6B C7B 176.6(2) . . . . ?
C5B C6B C7B C8B -0.3(4) . . . . ?
C5B C6B C7B C10B -179.8(3) . . . . ?
C6B C7B C8B C9B 1.0(4) . . . . ?
C10B C7B C8B C9B -179.5(3) . . . . ?
C7B C8B C9B C4B 0.4(4) . . . . ?
C7B C8B C9B I2B -176.8(2) . . . . ?
C5B C4B C9B C8B -2.3(4) . . . . ?
C1B C4B C9B C8B 177.2(2) . . . . ?
C5B C4B C9B I2B 174.68(18) . . . . ?
C1B C4B C9B I2B -5.8(3) . . . . ?
C4C C1C C2C O1C 173.8(2) . . . . ?
C4C C1C C2C C3C -64.6(3) . . . . ?
C11C O2C C3C C2C -173.3(2) . . . . ?
O1C C2C C3C O2C -62.9(3) . . . . ?
C1C C2C C3C O2C 178.8(2) . . . . ?
C2C C1C C4C C9C -77.0(3) . . . . ?
C2C C1C C4C C5C 100.9(3) . . . . ?
C9C C4C C5C C6C 2.3(4) . . . . ?
C1C C4C C5C C6C -175.8(3) . . . . ?
C9C C4C C5C I1C -178.12(18) . . . . ?
C1C C4C C5C I1C 3.8(4) . . . . ?
C4C C5C C6C C7C 0.4(4) . . . . ?
I1C C5C C6C C7C -179.2(2) . . . . ?
C5C C6C C7C C8C -2.7(4) . . . . ?
C5C C6C C7C C10C 177.9(3) . . . . ?
C6C C7C C8C C9C 2.1(4) . . . . ?
C10C C7C C8C C9C -178.4(3) . . . . ?
C7C C8C C9C C4C 0.7(4) . . . . ?
C7C C8C C9C I2C -177.5(2) . . . . ?
C5C C4C C9C C8C -2.9(4) . . . . ?
C1C C4C C9C C8C 175.2(2) . . . . ?
C5C C4C C9C I2C 175.30(18) . . . . ?
C1C C4C C9C I2C -6.6(3) . . . . ?
C4D C1D C2D O1D 175.2(2) . . . . ?
C4D C1D C2D C3D -62.9(3) . . . . ?
C11D O2D C3D C2D -178.4(2) . . . . ?
O1D C2D C3D O2D -66.9(3) . . . . ?
C1D C2D C3D O2D 174.5(2) . . . . ?
C2D C1D C4D C5D 100.6(3) . . . . ?
C2D C1D C4D C9D -78.8(3) . . . . ?
C9D C4D C5D C6D 1.6(4) . . . . ?
C1D C4D C5D C6D -177.8(3) . . . . ?
C9D C4D C5D I1D -178.67(19) . . . . ?
C1D C4D C5D I1D 1.9(4) . . . . ?
C4D C5D C6D C7D -0.7(4) . . . . ?
I1D C5D C6D C7D 179.6(2) . . . . ?
C5D C6D C7D C8D -1.2(4) . . . . ?
C5D C6D C7D C10D -179.9(3) . . . . ?
C6D C7D C8D C9D 2.1(4) . . . . ?
C10D C7D C8D C9D -179.3(3) . . . . ?
C7D C8D C9D C4D -1.1(4) . . . . ?
C7D C8D C9D I2D 179.6(2) . . . . ?
C5D C4D C9D C8D -0.8(4) . . . . ?
C1D C4D C9D C8D 178.7(3) . . . . ?
C5D C4D C9D I2D 178.53(19) . . . . ?
C1D C4D C9D I2D -2.0(4) . . . . ?
