#------------------------------------------------------------------------------
#$Date: 2020-08-04 05:21:03 +0300 (Tue, 04 Aug 2020) $
#$Revision: 254780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/85/4038547.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_4038547
loop_
_publ_author_name
'Tomanik, Martin'
'Economou, Christos'
'Frischling, Madeline C.'
'Xue, Mengzhao'
'Marks, Victoria A.'
'Mercado, Brandon Q.'
'Herzon, Seth B.'
_publ_section_title
;
 Development of a Convergent Enantioselective Synthetic Route to
 (-)-Myrocin G.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8952
_journal_page_last               8989
_journal_paper_doi               10.1021/acs.joc.0c00891
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C21 H31 I O4'
_chemical_formula_sum            'C21 H31 I O4'
_chemical_formula_weight         474.36
_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
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 110.142(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.2644(4)
_cell_length_b                   11.1326(3)
_cell_length_c                   23.6238(5)
_cell_measurement_reflns_used    40242
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      66.5160
_cell_measurement_theta_min      2.7060
_cell_volume                     4262.76(18)
_computing_cell_refinement       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_molecular_graphics
; 
Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., 
OLEX2: A complete structure solution, refinement and analysis program 
(2009). J. Appl. Cryst., 42, 339-341. 
;
_computing_publication_material  'CIFTAB-2014/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 22.2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0881
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            151643
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.598
_diffrn_reflns_theta_max         66.598
_diffrn_reflns_theta_min         2.726
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    11.978
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.39.16b (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.831
_refine_diff_density_min         -1.078
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         7514
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0402P)²+7.1715P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0892
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6222
_reflns_number_total             7514
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00891_si_001.cif
_cod_data_source_block           007-17082
_cod_depositor_comments
'Adding full bibliography for 4038544--4038549.cif.'
_cod_original_cell_volume        4262.75(18)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4038547
_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   0.380
_shelx_estimated_absorpt_t_max   0.796
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
I1 I 0.88123(2) 0.81427(3) 0.48582(2) 0.03470(9) Uani 1 1 d . . . . .
O1 O 0.73088(18) 1.0426(3) 0.47503(13) 0.0320(7) Uani 1 1 d D . . . .
H1 H 0.755(3) 1.070(5) 0.5086(13) 0.055(17) Uiso 1 1 d D . . . .
O2 O 0.66560(16) 0.6795(2) 0.43287(11) 0.0278(6) Uani 1 1 d . . . . .
O3 O 0.51435(16) 0.7398(3) 0.32008(12) 0.0302(6) Uani 1 1 d . . . . .
O4 O 0.53658(17) 0.5777(3) 0.26981(12) 0.0363(7) Uani 1 1 d . . . . .
C1 C 0.7818(2) 0.8498(4) 0.51681(17) 0.0256(8) Uani 1 1 d . . . . .
C2 C 0.7912(2) 0.8189(4) 0.57288(17) 0.0271(9) Uani 1 1 d . . . . .
H2 H 0.8404 0.7783 0.5957 0.032 Uiso 1 1 calc R U . . .
C3 C 0.7281(2) 0.8443(4) 0.60305(17) 0.0265(9) Uani 1 1 d . . . . .
C4 C 0.6629(2) 0.9315(4) 0.56481(17) 0.0280(9) Uani 1 1 d . . . . .
H4A H 0.6850 1.0143 0.5720 0.034 Uiso 1 1 calc R U . . .
H4B H 0.6139 0.9278 0.5775 0.034 Uiso 1 1 calc R U . . .
C5 C 0.6365(2) 0.9034(4) 0.49747(17) 0.0265(9) Uani 1 1 d . . . . .
H5A H 0.5912 0.9580 0.4748 0.032 Uiso 1 1 calc R U . . .
H5B H 0.6156 0.8199 0.4902 0.032 Uiso 1 1 calc R U . . .
C6 C 0.7091(2) 0.9182(3) 0.47468(17) 0.0246(8) Uani 1 1 d . . . . .
C7 C 0.6833(2) 0.8801(3) 0.40800(17) 0.0243(8) Uani 1 1 d . . . . .
C8 C 0.6664(2) 0.7519(4) 0.39384(17) 0.0240(8) Uani 1 1 d . . . . .
C9 C 0.6518(2) 0.7016(4) 0.32981(17) 0.0261(9) Uani 1 1 d . . . . .
C10 C 0.6655(3) 0.7931(4) 0.28474(18) 0.0317(9) Uani 1 1 d . . . . .
H10A H 0.6795 0.7493 0.2531 0.038 Uiso 1 1 calc R U . . .
H10B H 0.6137 0.8379 0.2649 0.038 Uiso 1 1 calc R U . . .
C11 C 0.7345(3) 0.8819(4) 0.31588(19) 0.0351(10) Uani 1 1 d . . . . .
H11A H 0.7871 0.8376 0.3334 0.042 Uiso 1 1 calc R U . . .
H11B H 0.7409 0.9390 0.2857 0.042 Uiso 1 1 calc R U . . .
C12 C 0.7167(3) 0.9511(4) 0.36522(18) 0.0311(9) Uani 1 1 d . . . . .
H12 H 0.7569 1.0163 0.3846 0.037 Uiso 1 1 calc R U . . .
C13 C 0.6305(3) 0.9727(4) 0.36234(18) 0.0308(9) Uani 1 1 d . . . . .
H13A H 0.5855 0.9418 0.3267 0.037 Uiso 1 1 calc R U . . .
H13B H 0.6184 1.0498 0.3784 0.037 Uiso 1 1 calc R U . . .
C14 C 0.6891(3) 0.7253(4) 0.61207(19) 0.0312(9) Uani 1 1 d . . . . .
H14A H 0.6620 0.6871 0.5728 0.047 Uiso 1 1 calc R U . . .
H14B H 0.6483 0.7409 0.6315 0.047 Uiso 1 1 calc R U . . .
H14C H 0.7322 0.6719 0.6376 0.047 Uiso 1 1 calc R U . . .
C15 C 0.7729(3) 0.9001(4) 0.66484(18) 0.0354(10) Uani 1 1 d . . . . .
H15A H 0.8144 0.8437 0.6895 0.053 Uiso 1 1 calc R U . . .
H15B H 0.7330 0.9177 0.6848 0.053 Uiso 1 1 calc R U . . .
H15C H 0.8000 0.9747 0.6598 0.053 Uiso 1 1 calc R U . . .
C16 C 0.5612(2) 0.6621(4) 0.30310(17) 0.0264(9) Uani 1 1 d . . . . .
C17 C 0.4230(2) 0.7344(4) 0.29729(18) 0.0315(10) Uani 1 1 d . . . . .
C18 C 0.3905(3) 0.7565(4) 0.23007(19) 0.0362(10) Uani 1 1 d . . . . .
H18A H 0.4140 0.8313 0.2211 0.054 Uiso 1 1 calc R U . . .
H18B H 0.3302 0.7632 0.2161 0.054 Uiso 1 1 calc R U . . .
H18C H 0.4062 0.6895 0.2094 0.054 Uiso 1 1 calc R U . . .
C19 C 0.3953(3) 0.6148(5) 0.3153(2) 0.0463(12) Uani 1 1 d . . . . .
H19A H 0.4066 0.5502 0.2910 0.069 Uiso 1 1 calc R U . . .
H19B H 0.3360 0.6178 0.3084 0.069 Uiso 1 1 calc R U . . .
H19C H 0.4256 0.5994 0.3581 0.069 Uiso 1 1 calc R U . . .
C20 C 0.4012(3) 0.8392(5) 0.3305(2) 0.0481(13) Uani 1 1 d . . . . .
H20A H 0.4280 0.8282 0.3740 0.072 Uiso 1 1 calc R U . . .
H20B H 0.3413 0.8425 0.3206 0.072 Uiso 1 1 calc R U . . .
H20C H 0.4203 0.9144 0.3182 0.072 Uiso 1 1 calc R U . . .
C21 C 0.7086(3) 0.5924(4) 0.33589(19) 0.0332(10) Uani 1 1 d . . . . .
H21A H 0.7662 0.6191 0.3496 0.050 Uiso 1 1 calc R U . . .
H21B H 0.6951 0.5526 0.2967 0.050 Uiso 1 1 calc R U . . .
H21C H 0.7006 0.5360 0.3652 0.050 Uiso 1 1 calc R U . . .
I2 I 0.84759(2) 0.30086(3) 0.44662(2) 0.03344(9) Uani 1 1 d . . . . .
O5 O 0.78340(18) 0.5396(3) 0.52331(14) 0.0340(7) Uani 1 1 d D . . . .
H5 H 0.744(2) 0.563(5) 0.4948(18) 0.07(2) Uiso 1 1 d D . . . .
O6 O 0.81007(16) 0.1801(2) 0.58377(12) 0.0269(6) Uani 1 1 d . . . . .
O7 O 0.90812(16) 0.2427(3) 0.71941(11) 0.0282(6) Uani 1 1 d . . . . .
O8 O 0.97982(18) 0.0700(3) 0.72527(13) 0.0372(7) Uani 1 1 d . . . . .
C22 C 0.7499(2) 0.3445(4) 0.47882(17) 0.0266(9) Uani 1 1 d . . . . .
C23 C 0.6741(2) 0.3125(4) 0.44538(17) 0.0270(9) Uani 1 1 d . . . . .
H23 H 0.6670 0.2692 0.4093 0.032 Uiso 1 1 calc R U . . .
C24 C 0.5978(2) 0.3404(4) 0.46081(18) 0.0275(9) Uani 1 1 d . . . . .
C25 C 0.6184(2) 0.4306(4) 0.51238(18) 0.0300(9) Uani 1 1 d . . . . .
H25A H 0.5747 0.4284 0.5306 0.036 Uiso 1 1 calc R U . . .
H25B H 0.6193 0.5124 0.4962 0.036 Uiso 1 1 calc R U . . .
C26 C 0.7017(2) 0.4052(4) 0.56130(17) 0.0271(9) Uani 1 1 d . . . . .
H26A H 0.7014 0.3231 0.5773 0.033 Uiso 1 1 calc R U . . .
H26B H 0.7106 0.4627 0.5949 0.033 Uiso 1 1 calc R U . . .
C27 C 0.7727(2) 0.4165(4) 0.53644(17) 0.0247(8) Uani 1 1 d . . . . .
C28 C 0.8551(2) 0.3799(3) 0.58363(16) 0.0225(8) Uani 1 1 d . . . . .
C29 C 0.8674(2) 0.2523(4) 0.60109(17) 0.0247(8) Uani 1 1 d . . . . .
C30 C 0.9531(2) 0.2024(4) 0.63896(17) 0.0268(9) Uani 1 1 d . . . . .
C31 C 1.0246(2) 0.2943(4) 0.65374(19) 0.0316(9) Uani 1 1 d . . . . .
H31A H 1.0279 0.3386 0.6909 0.038 Uiso 1 1 calc R U . . .
H31B H 1.0772 0.2507 0.6617 0.038 Uiso 1 1 calc R U . . .
C32 C 1.0135(2) 0.3835(4) 0.6029(2) 0.0336(10) Uani 1 1 d . . . . .
H32A H 1.0600 0.4413 0.6149 0.040 Uiso 1 1 calc R U . . .
H32B H 1.0147 0.3401 0.5667 0.040 Uiso 1 1 calc R U . . .
C33 C 0.9328(2) 0.4518(4) 0.58764(18) 0.0295(9) Uani 1 1 d . . . . .
H33 H 0.9244 0.5171 0.5570 0.035 Uiso 1 1 calc R U . . .
C34 C 0.8938(2) 0.4726(4) 0.63367(18) 0.0301(9) Uani 1 1 d . . . . .
H34A H 0.8640 0.5493 0.6319 0.036 Uiso 1 1 calc R U . . .
H34B H 0.9228 0.4420 0.6749 0.036 Uiso 1 1 calc R U . . .
C35 C 0.5327(3) 0.3934(4) 0.40478(19) 0.0356(10) Uani 1 1 d . . . . .
H35A H 0.5539 0.4676 0.3931 0.053 Uiso 1 1 calc R U . . .
H35B H 0.4825 0.4113 0.4137 0.053 Uiso 1 1 calc R U . . .
H35C H 0.5199 0.3354 0.3716 0.053 Uiso 1 1 calc R U . . .
C36 C 0.5640(3) 0.2239(4) 0.4778(2) 0.0333(10) Uani 1 1 d . . . . .
H36A H 0.5517 0.1669 0.4443 0.050 Uiso 1 1 calc R U . . .
H36B H 0.5135 0.2413 0.4864 0.050 Uiso 1 1 calc R U . . .
H36C H 0.6053 0.1891 0.5137 0.050 Uiso 1 1 calc R U . . .
C37 C 0.9485(2) 0.1602(4) 0.69912(18) 0.0280(9) Uani 1 1 d . . . . .
C38 C 0.9001(2) 0.2356(4) 0.77995(17) 0.0276(9) Uani 1 1 d . . . . .
C39 C 0.8509(3) 0.3476(4) 0.78110(19) 0.0357(10) Uani 1 1 d . . . . .
H39A H 0.8832 0.4188 0.7791 0.054 Uiso 1 1 calc R U . . .
H39B H 0.8383 0.3494 0.8185 0.054 Uiso 1 1 calc R U . . .
H39C H 0.7994 0.3470 0.7464 0.054 Uiso 1 1 calc R U . . .
C40 C 0.9845(3) 0.2433(4) 0.82803(19) 0.0376(11) Uani 1 1 d . . . . .
H40A H 1.0159 0.1705 0.8271 0.056 Uiso 1 1 calc R U . . .
H40B H 0.9786 0.2510 0.8677 0.056 Uiso 1 1 calc R U . . .
H40C H 1.0137 0.3136 0.8205 0.056 Uiso 1 1 calc R U . . .
C41 C 0.8530(3) 0.1226(4) 0.78333(19) 0.0379(11) Uani 1 1 d . . . . .
H41A H 0.8019 0.1190 0.7484 0.057 Uiso 1 1 calc R U . . .
H41B H 0.8396 0.1236 0.8204 0.057 Uiso 1 1 calc R U . . .
H41C H 0.8870 0.0521 0.7834 0.057 Uiso 1 1 calc R U . . .
C42 C 0.9705(3) 0.0944(4) 0.60464(18) 0.0304(9) Uani 1 1 d . . . . .
H42A H 0.9267 0.0345 0.5982 0.046 Uiso 1 1 calc R U . . .
H42B H 1.0237 0.0586 0.6283 0.046 Uiso 1 1 calc R U . . .
H42C H 0.9723 0.1212 0.5656 0.046 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 0.0181 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'
I I -0.3257 6.8362 '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'
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
C6 O1 H1 114(4) . . ?
C16 O3 C17 122.9(3) . . ?
C2 C1 C6 125.2(4) . . ?
C2 C1 I1 117.6(3) . . ?
C6 C1 I1 117.0(3) . . ?
C1 C2 C3 124.2(4) . . ?
C1 C2 H2 117.9 . . ?
C3 C2 H2 117.9 . . ?
C2 C3 C4 110.1(3) . . ?
C2 C3 C15 108.4(3) . . ?
C4 C3 C15 109.5(3) . . ?
C2 C3 C14 108.9(3) . . ?
C4 C3 C14 111.2(3) . . ?
C15 C3 C14 108.7(3) . . ?
C3 C4 C5 112.3(3) . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.9 . . ?
C4 C5 C6 110.9(3) . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.0 . . ?
O1 C6 C1 109.0(3) . . ?
O1 C6 C5 110.3(3) . . ?
C1 C6 C5 108.0(3) . . ?
O1 C6 C7 104.7(3) . . ?
C1 C6 C7 114.6(3) . . ?
C5 C6 C7 110.2(3) . . ?
C8 C7 C6 117.7(3) . . ?
C8 C7 C13 117.8(3) . . ?
C6 C7 C13 115.1(3) . . ?
C8 C7 C12 115.9(3) . . ?
C6 C7 C12 119.1(3) . . ?
C13 C7 C12 57.6(3) . . ?
O2 C8 C7 121.2(3) . . ?
O2 C8 C9 117.1(4) . . ?
C7 C8 C9 121.7(3) . . ?
C16 C9 C21 109.8(3) . . ?
C16 C9 C10 106.3(3) . . ?
C21 C9 C10 109.9(3) . . ?
C16 C9 C8 107.7(3) . . ?
C21 C9 C8 108.1(3) . . ?
C10 C9 C8 114.8(3) . . ?
C11 C10 C9 111.9(3) . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C10 111.6(4) . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C13 C12 C11 120.8(4) . . ?
C13 C12 C7 61.2(3) . . ?
C11 C12 C7 117.7(4) . . ?
C13 C12 H12 115.4 . . ?
C11 C12 H12 115.4 . . ?
C7 C12 H12 115.4 . . ?
C12 C13 C7 61.2(3) . . ?
C12 C13 H13A 117.6 . . ?
C7 C13 H13A 117.6 . . ?
C12 C13 H13B 117.6 . . ?
C7 C13 H13B 117.6 . . ?
H13A C13 H13B 114.8 . . ?
C3 C14 H14A 109.5 . . ?
C3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 C15 H15A 109.5 . . ?
C3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 O3 125.9(4) . . ?
O4 C16 C9 124.9(4) . . ?
O3 C16 C9 109.1(3) . . ?
O3 C17 C18 109.8(3) . . ?
O3 C17 C20 101.7(3) . . ?
C18 C17 C20 110.4(4) . . ?
O3 C17 C19 109.3(3) . . ?
C18 C17 C19 113.4(4) . . ?
C20 C17 C19 111.6(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C9 C21 H21A 109.5 . . ?
C9 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C9 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C27 O5 H5 111(4) . . ?
C37 O7 C38 122.7(3) . . ?
C23 C22 C27 125.3(4) . . ?
C23 C22 I2 117.9(3) . . ?
C27 C22 I2 116.7(3) . . ?
C22 C23 C24 124.4(4) . . ?
C22 C23 H23 117.8 . . ?
C24 C23 H23 117.8 . . ?
C23 C24 C25 110.1(3) . . ?
C23 C24 C35 108.2(3) . . ?
C25 C24 C35 109.8(3) . . ?
C23 C24 C36 109.3(3) . . ?
C25 C24 C36 110.7(3) . . ?
C35 C24 C36 108.8(3) . . ?
C24 C25 C26 112.5(3) . . ?
C24 C25 H25A 109.1 . . ?
C26 C25 H25A 109.1 . . ?
C24 C25 H25B 109.1 . . ?
C26 C25 H25B 109.1 . . ?
H25A C25 H25B 107.8 . . ?
C25 C26 C27 111.3(3) . . ?
C25 C26 H26A 109.4 . . ?
C27 C26 H26A 109.4 . . ?
C25 C26 H26B 109.4 . . ?
C27 C26 H26B 109.4 . . ?
H26A C26 H26B 108.0 . . ?
O5 C27 C22 109.0(3) . . ?
O5 C27 C28 104.9(3) . . ?
C22 C27 C28 113.8(3) . . ?
O5 C27 C26 109.9(3) . . ?
C22 C27 C26 107.8(3) . . ?
C28 C27 C26 111.3(3) . . ?
C29 C28 C27 118.0(3) . . ?
C29 C28 C33 116.5(3) . . ?
C27 C28 C33 118.6(3) . . ?
C29 C28 C34 116.7(3) . . ?
C27 C28 C34 115.5(3) . . ?
C33 C28 C34 57.6(2) . . ?
O6 C29 C28 121.0(3) . . ?
O6 C29 C30 117.3(4) . . ?
C28 C29 C30 121.7(3) . . ?
C37 C30 C42 109.5(3) . . ?
C37 C30 C29 107.7(3) . . ?
C42 C30 C29 107.4(3) . . ?
C37 C30 C31 106.6(3) . . ?
C42 C30 C31 110.5(3) . . ?
C29 C30 C31 115.1(3) . . ?
C32 C31 C30 112.4(3) . . ?
C32 C31 H31A 109.1 . . ?
C30 C31 H31A 109.1 . . ?
C32 C31 H31B 109.1 . . ?
C30 C31 H31B 109.1 . . ?
H31A C31 H31B 107.9 . . ?
C33 C32 C31 111.7(3) . . ?
C33 C32 H32A 109.3 . . ?
C31 C32 H32A 109.3 . . ?
C33 C32 H32B 109.3 . . ?
C31 C32 H32B 109.3 . . ?
H32A C32 H32B 107.9 . . ?
C34 C33 C32 121.1(4) . . ?
C34 C33 C28 61.2(3) . . ?
C32 C33 C28 117.7(3) . . ?
C34 C33 H33 115.3 . . ?
C32 C33 H33 115.3 . . ?
C28 C33 H33 115.3 . . ?
C33 C34 C28 61.2(3) . . ?
C33 C34 H34A 117.6 . . ?
C28 C34 H34A 117.6 . . ?
C33 C34 H34B 117.6 . . ?
C28 C34 H34B 117.6 . . ?
H34A C34 H34B 114.8 . . ?
C24 C35 H35A 109.5 . . ?
C24 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C24 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C24 C36 H36A 109.5 . . ?
C24 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C24 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O8 C37 O7 125.8(4) . . ?
O8 C37 C30 125.2(4) . . ?
O7 C37 C30 108.9(3) . . ?
O7 C38 C40 109.6(3) . . ?
O7 C38 C39 102.2(3) . . ?
C40 C38 C39 109.9(4) . . ?
O7 C38 C41 109.0(3) . . ?
C40 C38 C41 113.9(4) . . ?
C39 C38 C41 111.6(4) . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C38 C40 H40A 109.5 . . ?
C38 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C38 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C38 C41 H41A 109.5 . . ?
C38 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C38 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C30 C42 H42A 109.5 . . ?
C30 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C30 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
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
I1 C1 2.122(4) . ?
O1 C6 1.434(5) . ?
O1 H1 0.817(19) . ?
O2 C8 1.229(5) . ?
O3 C16 1.337(5) . ?
O3 C17 1.482(5) . ?
O4 C16 1.205(5) . ?
C1 C2 1.324(6) . ?
C1 C6 1.512(5) . ?
C2 C3 1.518(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.526(5) . ?
C3 C15 1.529(5) . ?
C3 C14 1.534(6) . ?
C4 C5 1.529(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.533(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.541(5) . ?
C7 C8 1.471(6) . ?
C7 C13 1.543(5) . ?
C7 C12 1.543(5) . ?
C8 C9 1.550(5) . ?
C9 C16 1.536(5) . ?
C9 C21 1.536(5) . ?
C9 C10 1.550(6) . ?
C10 C11 1.528(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.514(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.486(6) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C17 C18 1.511(6) . ?
C17 C20 1.523(6) . ?
C17 C19 1.525(6) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
I2 C22 2.132(4) . ?
O5 C27 1.431(5) . ?
O5 H5 0.82(2) . ?
O6 C29 1.230(5) . ?
O7 C37 1.338(5) . ?
O7 C38 1.485(5) . ?
O8 C37 1.205(5) . ?
C22 C23 1.323(6) . ?
C22 C27 1.511(5) . ?
C23 C24 1.515(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.523(6) . ?
C24 C35 1.529(5) . ?
C24 C36 1.531(6) . ?
C25 C26 1.529(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.535(5) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.530(5) . ?
C28 C29 1.474(6) . ?
C28 C33 1.538(5) . ?
C28 C34 1.538(5) . ?
C29 C30 1.545(5) . ?
C30 C37 1.525(5) . ?
C30 C42 1.537(5) . ?
C30 C31 1.547(6) . ?
C31 C32 1.519(6) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.517(6) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.481(6) . ?
C33 H33 1.0000 . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C38 C40 1.509(6) . ?
C38 C39 1.514(6) . ?
C38 C41 1.515(6) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
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
O5 H5 O2 0.82(2) 2.07(3) 2.852(4) 160(6) .
O1 H1 O6 0.817(19) 2.10(2) 2.897(4) 166(5) 1_565
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
C6 C1 C2 C3 2.1(6) . . . . ?
I1 C1 C2 C3 176.4(3) . . . . ?
C1 C2 C3 C4 -11.7(5) . . . . ?
C1 C2 C3 C15 -131.5(4) . . . . ?
C1 C2 C3 C14 110.4(4) . . . . ?
C2 C3 C4 C5 41.3(4) . . . . ?
C15 C3 C4 C5 160.4(3) . . . . ?
C14 C3 C4 C5 -79.5(4) . . . . ?
C3 C4 C5 C6 -63.5(4) . . . . ?
C2 C1 C6 O1 98.6(5) . . . . ?
I1 C1 C6 O1 -75.8(3) . . . . ?
C2 C1 C6 C5 -21.1(5) . . . . ?
I1 C1 C6 C5 164.5(3) . . . . ?
C2 C1 C6 C7 -144.4(4) . . . . ?
I1 C1 C6 C7 41.2(4) . . . . ?
C4 C5 C6 O1 -69.2(4) . . . . ?
C4 C5 C6 C1 49.8(4) . . . . ?
C4 C5 C6 C7 175.6(3) . . . . ?
O1 C6 C7 C8 173.0(3) . . . . ?
C1 C6 C7 C8 53.6(5) . . . . ?
C5 C6 C7 C8 -68.4(4) . . . . ?
O1 C6 C7 C13 -41.2(4) . . . . ?
C1 C6 C7 C13 -160.6(3) . . . . ?
C5 C6 C7 C13 77.4(4) . . . . ?
O1 C6 C7 C12 24.1(4) . . . . ?
C1 C6 C7 C12 -95.3(4) . . . . ?
C5 C6 C7 C12 142.7(4) . . . . ?
C6 C7 C8 O2 6.5(5) . . . . ?
C13 C7 C8 O2 -138.3(4) . . . . ?
C12 C7 C8 O2 156.4(4) . . . . ?
C6 C7 C8 C9 -171.5(3) . . . . ?
C13 C7 C8 C9 43.7(5) . . . . ?
C12 C7 C8 C9 -21.6(5) . . . . ?
O2 C8 C9 C16 69.9(4) . . . . ?
C7 C8 C9 C16 -112.0(4) . . . . ?
O2 C8 C9 C21 -48.7(5) . . . . ?
C7 C8 C9 C21 129.3(4) . . . . ?
O2 C8 C9 C10 -171.9(3) . . . . ?
C7 C8 C9 C10 6.2(5) . . . . ?
C16 C9 C10 C11 153.0(3) . . . . ?
C21 C9 C10 C11 -88.2(4) . . . . ?
C8 C9 C10 C11 33.9(5) . . . . ?
C9 C10 C11 C12 -58.5(5) . . . . ?
C10 C11 C12 C13 -27.3(5) . . . . ?
C10 C11 C12 C7 43.9(5) . . . . ?
C8 C7 C12 C13 107.8(4) . . . . ?
C6 C7 C12 C13 -102.8(4) . . . . ?
C8 C7 C12 C11 -4.1(5) . . . . ?
C6 C7 C12 C11 145.4(4) . . . . ?
C13 C7 C12 C11 -111.8(4) . . . . ?
C11 C12 C13 C7 106.8(4) . . . . ?
C8 C7 C13 C12 -104.5(4) . . . . ?
C6 C7 C13 C12 109.8(4) . . . . ?
C17 O3 C16 O4 -2.7(6) . . . . ?
C17 O3 C16 C9 174.0(3) . . . . ?
C21 C9 C16 O4 -28.4(5) . . . . ?
C10 C9 C16 O4 90.5(5) . . . . ?
C8 C9 C16 O4 -145.9(4) . . . . ?
C21 C9 C16 O3 154.9(3) . . . . ?
C10 C9 C16 O3 -86.2(4) . . . . ?
C8 C9 C16 O3 37.4(4) . . . . ?
C16 O3 C17 C18 -63.7(5) . . . . ?
C16 O3 C17 C20 179.4(4) . . . . ?
C16 O3 C17 C19 61.3(5) . . . . ?
C27 C22 C23 C24 -1.9(6) . . . . ?
I2 C22 C23 C24 -177.9(3) . . . . ?
C22 C23 C24 C25 11.4(5) . . . . ?
C22 C23 C24 C35 131.3(4) . . . . ?
C22 C23 C24 C36 -110.4(5) . . . . ?
C23 C24 C25 C26 -40.7(5) . . . . ?
C35 C24 C25 C26 -159.7(4) . . . . ?
C36 C24 C25 C26 80.2(4) . . . . ?
C24 C25 C26 C27 62.8(5) . . . . ?
C23 C22 C27 O5 -98.5(5) . . . . ?
I2 C22 C27 O5 77.5(3) . . . . ?
C23 C22 C27 C28 144.8(4) . . . . ?
I2 C22 C27 C28 -39.2(4) . . . . ?
C23 C22 C27 C26 20.8(5) . . . . ?
I2 C22 C27 C26 -163.2(3) . . . . ?
C25 C26 C27 O5 69.6(4) . . . . ?
C25 C26 C27 C22 -49.2(4) . . . . ?
C25 C26 C27 C28 -174.7(3) . . . . ?
O5 C27 C28 C29 -172.5(3) . . . . ?
C22 C27 C28 C29 -53.4(5) . . . . ?
C26 C27 C28 C29 68.7(4) . . . . ?
O5 C27 C28 C33 -22.6(4) . . . . ?
C22 C27 C28 C33 96.5(4) . . . . ?
C26 C27 C28 C33 -141.5(4) . . . . ?
O5 C27 C28 C34 42.8(4) . . . . ?
C22 C27 C28 C34 161.8(3) . . . . ?
C26 C27 C28 C34 -76.1(4) . . . . ?
C27 C28 C29 O6 -8.4(5) . . . . ?
C33 C28 C29 O6 -159.0(4) . . . . ?
C34 C28 C29 O6 135.9(4) . . . . ?
C27 C28 C29 C30 168.4(3) . . . . ?
C33 C28 C29 C30 17.9(5) . . . . ?
C34 C28 C29 C30 -47.3(5) . . . . ?
O6 C29 C30 C37 -67.5(4) . . . . ?
C28 C29 C30 C37 115.5(4) . . . . ?
O6 C29 C30 C42 50.3(5) . . . . ?
C28 C29 C30 C42 -126.7(4) . . . . ?
O6 C29 C30 C31 173.8(3) . . . . ?
C28 C29 C30 C31 -3.2(5) . . . . ?
C37 C30 C31 C32 -154.1(3) . . . . ?
C42 C30 C31 C32 87.1(4) . . . . ?
C29 C30 C31 C32 -34.7(5) . . . . ?
C30 C31 C32 C33 57.7(5) . . . . ?
C31 C32 C33 C34 27.7(5) . . . . ?
C31 C32 C33 C28 -43.7(5) . . . . ?
C29 C28 C33 C34 -106.1(4) . . . . ?
C27 C28 C33 C34 103.5(4) . . . . ?
C29 C28 C33 C32 6.0(5) . . . . ?
C27 C28 C33 C32 -144.3(4) . . . . ?
C34 C28 C33 C32 112.1(4) . . . . ?
C32 C33 C34 C28 -106.7(4) . . . . ?
C29 C28 C34 C33 105.8(4) . . . . ?
C27 C28 C34 C33 -109.0(4) . . . . ?
C38 O7 C37 O8 3.1(6) . . . . ?
C38 O7 C37 C30 -173.6(3) . . . . ?
C42 C30 C37 O8 23.1(5) . . . . ?
C29 C30 C37 O8 139.5(4) . . . . ?
C31 C30 C37 O8 -96.5(5) . . . . ?
C42 C30 C37 O7 -160.2(3) . . . . ?
C29 C30 C37 O7 -43.8(4) . . . . ?
C31 C30 C37 O7 80.2(4) . . . . ?
C37 O7 C38 C40 63.0(5) . . . . ?
C37 O7 C38 C39 179.6(3) . . . . ?
C37 O7 C38 C41 -62.2(5) . . . . ?
