# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelxl
_audit_block_doi                 10.5517/ccdc.csd.cc1nk7jz
_database_code_depnum_ccdc_archive 'CCDC 1535911'
_audit_update_record             
;
2017-03-03 deposited with the CCDC.
2017-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H28 O7'
_chemical_formula_sum            'C21 H28 O7'
_chemical_formula_weight         392.43

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   8.087(2)
_cell_length_b                   10.797(3)
_cell_length_c                   22.609(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1974.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1119
_cell_measurement_theta_min      30.10
_cell_measurement_theta_max      74.70

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.817
_shelx_estimated_absorpt_T_min   0.867
_shelx_estimated_absorpt_T_max   0.894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.794
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            16798
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         6.731
_diffrn_reflns_theta_max         75.109
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4036
_reflns_number_gt                3842
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_refine_special_details          
; 
    ENTER TEXT OF LETTER 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0454P)²+0.2846P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1610 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.01(4)
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_refine_ls_number_reflns         4036
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0841
_refine_ls_wR_factor_gt          0.0828
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.5765(2) 0.29104(14) 0.24936(8) 0.0468(4) Uani 1 1 d . . . . .
O2 O 0.5891(3) 0.1494(2) 0.35853(9) 0.0830(7) Uani 1 1 d . . . . .
O3 O 0.3253(3) 0.2047(2) 0.36369(7) 0.0728(6) Uani 1 1 d . . . . .
O4 O 0.57696(19) 0.07200(12) 0.19430(7) 0.0419(3) Uani 1 1 d . . . . .
O5 O 0.52233(16) 0.13524(12) 0.04411(6) 0.0348(3) Uani 1 1 d . . . . .
O6 O 0.48399(17) 0.09400(13) -0.05556(5) 0.0374(3) Uani 1 1 d . . . . .
O7 O 0.3113(2) 0.1568(2) -0.12588(7) 0.0620(5) Uani 1 1 d . . . . .
C1 C 0.4444(3) 0.21508(18) 0.26825(8) 0.0393(4) Uani 1 1 d . . . . .
C2 C 0.4653(4) 0.1846(2) 0.33427(10) 0.0589(7) Uani 1 1 d . . . . .
C3 C 0.1914(4) 0.2454(3) 0.32399(10) 0.0589(6) Uani 1 1 d . . . . .
C4 C 0.2812(3) 0.28645(18) 0.26734(8) 0.0373(4) Uani 1 1 d . . . . .
H4 H 0.3094 0.3760 0.2725 0.045 Uiso 1 1 calc R U . . .
C5 C 0.1790(2) 0.27675(19) 0.21073(8) 0.0368(4) Uani 1 1 d . . . . .
H5A H 0.1424 0.1899 0.2056 0.044 Uiso 1 1 calc R U . . .
H5B H 0.0790 0.3289 0.2148 0.044 Uiso 1 1 calc R U . . .
C6 C 0.2737(3) 0.31702(18) 0.15566(8) 0.0384(4) Uani 1 1 d . . . . .
H6A H 0.3253 0.3984 0.1638 0.046 Uiso 1 1 calc R U . . .
H6B H 0.1932 0.3290 0.1232 0.046 Uiso 1 1 calc R U . . .
C7 C 0.4107(2) 0.22712(16) 0.13370(8) 0.0311(4) Uani 1 1 d . . . . .
H7 H 0.5209 0.2691 0.1349 0.037 Uiso 1 1 calc R U . . .
C8 C 0.4185(2) 0.10430(16) 0.16717(8) 0.0308(4) Uani 1 1 d . . . . .
C9 C 0.4359(3) 0.09582(17) 0.23155(8) 0.0356(4) Uani 1 1 d . . . . .
H9 H 0.3841 0.0223 0.2510 0.043 Uiso 1 1 calc R U . . .
C10 C 0.3352(3) 0.00234(17) 0.13110(7) 0.0353(4) Uani 1 1 d . . . . .
H10A H 0.2455 -0.0372 0.1541 0.042 Uiso 1 1 calc R U . . .
H10B H 0.4163 -0.0619 0.1196 0.042 Uiso 1 1 calc R U . . .
C11 C 0.2645(2) 0.06845(16) 0.07561(7) 0.0301(4) Uani 1 1 d . . . . .
H11 H 0.1452 0.0903 0.0807 0.036 Uiso 1 1 calc R U . . .
C12 C 0.3730(2) 0.18366(17) 0.07081(8) 0.0307(4) Uani 1 1 d . . . . .
H12 H 0.3207 0.2500 0.0463 0.037 Uiso 1 1 calc R U . . .
C13 C 0.4812(2) 0.04075(15) 0.00384(7) 0.0288(4) Uani 1 1 d . . . . .
C14 C 0.2966(2) 0.00361(16) 0.01594(7) 0.0289(4) Uani 1 1 d . . . . .
C15 C 0.2022(2) 0.06754(18) -0.03496(8) 0.0341(4) Uani 1 1 d . . . . .
H15A H 0.1260 0.0084 -0.0544 0.041 Uiso 1 1 calc R U . . .
H15B H 0.1369 0.1382 -0.0197 0.041 Uiso 1 1 calc R U . . .
C16 C 0.3309(3) 0.1117(2) -0.07794(8) 0.0401(4) Uani 1 1 d . . . . .
C17 C 0.1082(5) 0.3541(4) 0.35439(12) 0.0811(10) Uani 1 1 d . . . . .
H17A H 0.1908 0.4179 0.3632 0.097 Uiso 1 1 calc R U . . .
H17B H 0.0570 0.3260 0.3913 0.097 Uiso 1 1 calc R U . . .
H17C H 0.0231 0.3887 0.3283 0.097 Uiso 1 1 calc R U . . .
C18 C 0.0754(5) 0.1356(3) 0.31695(14) 0.0839(10) Uani 1 1 d . . . . .
H18A H 0.0351 0.1098 0.3559 0.101 Uiso 1 1 calc R U . . .
H18B H 0.1348 0.0668 0.2983 0.101 Uiso 1 1 calc R U . . .
H18C H -0.0185 0.1595 0.2921 0.101 Uiso 1 1 calc R U . . .
C19 C 0.6113(2) -0.05981(17) 0.00514(9) 0.0345(4) Uani 1 1 d . . . . .
H19A H 0.5855 -0.1215 -0.0259 0.041 Uiso 1 1 calc R U . . .
H19B H 0.6060 -0.1026 0.0438 0.041 Uiso 1 1 calc R U . . .
C20 C 0.7863(3) -0.0125(2) -0.00435(10) 0.0422(5) Uani 1 1 d . . . . .
H20A H 0.7947 0.0256 -0.0436 0.051 Uiso 1 1 calc R U . . .
H20B H 0.8642 -0.0818 -0.0016 0.051 Uiso 1 1 calc R U . . .
H20C H 0.8128 0.0492 0.0260 0.051 Uiso 1 1 calc R U . . .
C21 C 0.2626(3) -0.13607(17) 0.01599(8) 0.0355(4) Uani 1 1 d . . . . .
H21A H 0.3311 -0.1761 0.0462 0.043 Uiso 1 1 calc R U . . .
H21B H 0.2894 -0.1705 -0.0229 0.043 Uiso 1 1 calc R U . . .
H21C H 0.1456 -0.1508 0.0248 0.043 Uiso 1 1 calc R U . . .
H1 H 0.639(4) 0.247(3) 0.2298(15) 0.075(10) Uiso 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
O1 C1 1.413(3) . ?
O1 H1 0.82(4) . ?
O2 C2 1.203(3) . ?
O3 C2 1.331(4) . ?
O3 C3 1.474(3) . ?
O4 C9 1.441(3) . ?
O4 C8 1.463(2) . ?
O5 C13 1.407(2) . ?
O5 C12 1.448(2) . ?
O6 C16 1.351(3) . ?
O6 C13 1.461(2) . ?
O7 C16 1.199(2) . ?
C1 C4 1.528(3) . ?
C1 C9 1.533(3) . ?
C1 C2 1.538(3) . ?
C3 C17 1.518(4) . ?
C3 C18 1.520(5) . ?
C3 C4 1.538(3) . ?
C4 C5 1.527(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.525(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.555(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C12 1.528(2) . ?
C7 C8 1.528(2) . ?
C7 H7 1.0000 . ?
C8 C9 1.465(2) . ?
C8 C10 1.527(2) . ?
C9 H9 1.0000 . ?
C10 C11 1.553(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.526(2) . ?
C11 C14 1.542(2) . ?
C11 H11 1.0000 . ?
C12 H12 1.0000 . ?
C13 C19 1.512(2) . ?
C13 C14 1.570(3) . ?
C14 C21 1.533(3) . ?
C14 C15 1.544(2) . ?
C15 C16 1.502(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.520(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C1 O1 H1 107(2) . . ?
C2 O3 C3 111.67(17) . . ?
C9 O4 C8 60.61(12) . . ?
C13 O5 C12 109.52(13) . . ?
C16 O6 C13 112.69(14) . . ?
O1 C1 C4 110.86(16) . . ?
O1 C1 C9 110.96(17) . . ?
C4 C1 C9 112.18(17) . . ?
O1 C1 C2 109.52(19) . . ?
C4 C1 C2 102.47(18) . . ?
C9 C1 C2 110.53(16) . . ?
O2 C2 O3 122.1(2) . . ?
O2 C2 C1 127.0(3) . . ?
O3 C2 C1 110.9(2) . . ?
O3 C3 C17 106.3(2) . . ?
O3 C3 C18 106.6(2) . . ?
C17 C3 C18 112.1(3) . . ?
O3 C3 C4 104.3(2) . . ?
C17 C3 C4 111.3(2) . . ?
C18 C3 C4 115.4(2) . . ?
C5 C4 C1 116.36(15) . . ?
C5 C4 C3 115.0(2) . . ?
C1 C4 C3 104.55(18) . . ?
C5 C4 H4 106.8 . . ?
C1 C4 H4 106.8 . . ?
C3 C4 H4 106.8 . . ?
C6 C5 C4 113.13(17) . . ?
C6 C5 H5A 109.0 . . ?
C4 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C5 C6 C7 116.15(15) . . ?
C5 C6 H6A 108.2 . . ?
C7 C6 H6A 108.2 . . ?
C5 C6 H6B 108.2 . . ?
C7 C6 H6B 108.2 . . ?
H6A C6 H6B 107.4 . . ?
C12 C7 C8 101.68(14) . . ?
C12 C7 C6 110.27(15) . . ?
C8 C7 C6 114.40(15) . . ?
C12 C7 H7 110.1 . . ?
C8 C7 H7 110.1 . . ?
C6 C7 H7 110.1 . . ?
O4 C8 C9 58.97(12) . . ?
O4 C8 C10 116.02(15) . . ?
C9 C8 C10 121.86(16) . . ?
O4 C8 C7 116.79(15) . . ?
C9 C8 C7 123.37(15) . . ?
C10 C8 C7 110.06(15) . . ?
O4 C9 C8 60.42(12) . . ?
O4 C9 C1 115.52(17) . . ?
C8 C9 C1 119.30(16) . . ?
O4 C9 H9 116.6 . . ?
C8 C9 H9 116.6 . . ?
C1 C9 H9 116.6 . . ?
C8 C10 C11 105.23(14) . . ?
C8 C10 H10A 110.7 . . ?
C11 C10 H10A 110.7 . . ?
C8 C10 H10B 110.7 . . ?
C11 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
C12 C11 C14 102.19(13) . . ?
C12 C11 C10 102.73(14) . . ?
C14 C11 C10 115.87(15) . . ?
C12 C11 H11 111.8 . . ?
C14 C11 H11 111.8 . . ?
C10 C11 H11 111.8 . . ?
O5 C12 C11 102.41(14) . . ?
O5 C12 C7 109.41(15) . . ?
C11 C12 C7 107.40(14) . . ?
O5 C12 H12 112.4 . . ?
C11 C12 H12 112.4 . . ?
C7 C12 H12 112.4 . . ?
O5 C13 O6 107.80(13) . . ?
O5 C13 C19 110.07(15) . . ?
O6 C13 C19 106.83(14) . . ?
O5 C13 C14 107.30(13) . . ?
O6 C13 C14 106.00(14) . . ?
C19 C13 C14 118.36(14) . . ?
C21 C14 C11 114.57(14) . . ?
C21 C14 C15 110.59(15) . . ?
C11 C14 C15 111.46(15) . . ?
C21 C14 C13 114.96(15) . . ?
C11 C14 C13 101.34(13) . . ?
C15 C14 C13 103.07(13) . . ?
C16 C15 C14 106.35(15) . . ?
C16 C15 H15A 110.5 . . ?
C14 C15 H15A 110.5 . . ?
C16 C15 H15B 110.5 . . ?
C14 C15 H15B 110.5 . . ?
H15A C15 H15B 108.7 . . ?
O7 C16 O6 121.18(19) . . ?
O7 C16 C15 128.5(2) . . ?
O6 C16 C15 110.35(15) . . ?
C3 C17 H17A 109.5 . . ?
C3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C19 C20 113.82(16) . . ?
C13 C19 H19A 108.8 . . ?
C20 C19 H19A 108.8 . . ?
C13 C19 H19B 108.8 . . ?
C20 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C14 C21 H21A 109.5 . . ?
C14 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C14 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 O3 C2 O2 -179.1(2) . . . . ?
C3 O3 C2 C1 2.1(3) . . . . ?
O1 C1 C2 O2 -47.5(3) . . . . ?
C4 C1 C2 O2 -165.2(2) . . . . ?
C9 C1 C2 O2 75.1(3) . . . . ?
O1 C1 C2 O3 131.2(2) . . . . ?
C4 C1 C2 O3 13.5(3) . . . . ?
C9 C1 C2 O3 -106.2(2) . . . . ?
C2 O3 C3 C17 -134.6(2) . . . . ?
C2 O3 C3 C18 105.7(3) . . . . ?
C2 O3 C3 C4 -16.9(3) . . . . ?
O1 C1 C4 C5 92.6(2) . . . . ?
C9 C1 C4 C5 -32.1(2) . . . . ?
C2 C1 C4 C5 -150.65(19) . . . . ?
O1 C1 C4 C3 -139.40(18) . . . . ?
C9 C1 C4 C3 95.9(2) . . . . ?
C2 C1 C4 C3 -22.6(2) . . . . ?
O3 C3 C4 C5 153.16(19) . . . . ?
C17 C3 C4 C5 -92.6(3) . . . . ?
C18 C3 C4 C5 36.6(3) . . . . ?
O3 C3 C4 C1 24.3(2) . . . . ?
C17 C3 C4 C1 138.5(2) . . . . ?
C18 C3 C4 C1 -92.2(3) . . . . ?
C1 C4 C5 C6 -56.6(2) . . . . ?
C3 C4 C5 C6 -179.34(18) . . . . ?
C4 C5 C6 C7 72.5(2) . . . . ?
C5 C6 C7 C12 119.85(18) . . . . ?
C5 C6 C7 C8 6.0(2) . . . . ?
C9 O4 C8 C10 -113.07(18) . . . . ?
C9 O4 C8 C7 114.54(17) . . . . ?
C12 C7 C8 O4 117.28(16) . . . . ?
C6 C7 C8 O4 -123.88(17) . . . . ?
C12 C7 C8 C9 -173.75(18) . . . . ?
C6 C7 C8 C9 -54.9(3) . . . . ?
C12 C7 C8 C10 -17.77(19) . . . . ?
C6 C7 C8 C10 101.07(18) . . . . ?
C8 O4 C9 C1 -110.65(17) . . . . ?
C10 C8 C9 O4 103.24(19) . . . . ?
C7 C8 C9 O4 -103.51(19) . . . . ?
O4 C8 C9 C1 104.4(2) . . . . ?
C10 C8 C9 C1 -152.32(19) . . . . ?
C7 C8 C9 C1 0.9(3) . . . . ?
O1 C1 C9 O4 11.6(2) . . . . ?
C4 C1 C9 O4 136.18(17) . . . . ?
C2 C1 C9 O4 -110.1(2) . . . . ?
O1 C1 C9 C8 -57.4(2) . . . . ?
C4 C1 C9 C8 67.2(2) . . . . ?
C2 C1 C9 C8 -179.1(2) . . . . ?
O4 C8 C10 C11 -139.15(16) . . . . ?
C9 C8 C10 C11 152.69(17) . . . . ?
C7 C8 C10 C11 -3.7(2) . . . . ?
C8 C10 C11 C12 23.75(18) . . . . ?
C8 C10 C11 C14 134.24(16) . . . . ?
C13 O5 C12 C11 35.14(17) . . . . ?
C13 O5 C12 C7 148.85(14) . . . . ?
C14 C11 C12 O5 -41.54(16) . . . . ?
C10 C11 C12 O5 78.89(15) . . . . ?
C14 C11 C12 C7 -156.72(14) . . . . ?
C10 C11 C12 C7 -36.30(18) . . . . ?
C8 C7 C12 O5 -76.94(17) . . . . ?
C6 C7 C12 O5 161.31(14) . . . . ?
C8 C7 C12 C11 33.49(18) . . . . ?
C6 C7 C12 C11 -88.25(18) . . . . ?
C12 O5 C13 O6 99.75(15) . . . . ?
C12 O5 C13 C19 -144.07(15) . . . . ?
C12 O5 C13 C14 -14.03(17) . . . . ?
C16 O6 C13 O5 -105.74(18) . . . . ?
C16 O6 C13 C19 135.99(17) . . . . ?
C16 O6 C13 C14 8.90(19) . . . . ?
C12 C11 C14 C21 156.83(16) . . . . ?
C10 C11 C14 C21 46.0(2) . . . . ?
C12 C11 C14 C15 -76.64(18) . . . . ?
C10 C11 C14 C15 172.56(15) . . . . ?
C12 C11 C14 C13 32.43(16) . . . . ?
C10 C11 C14 C13 -78.38(17) . . . . ?
O5 C13 C14 C21 -136.67(15) . . . . ?
O6 C13 C14 C21 108.35(16) . . . . ?
C19 C13 C14 C21 -11.5(2) . . . . ?
O5 C13 C14 C11 -12.53(17) . . . . ?
O6 C13 C14 C11 -127.51(14) . . . . ?
C19 C13 C14 C11 112.68(16) . . . . ?
O5 C13 C14 C15 102.91(16) . . . . ?
O6 C13 C14 C15 -12.07(17) . . . . ?
C19 C13 C14 C15 -131.88(16) . . . . ?
C21 C14 C15 C16 -112.13(17) . . . . ?
C11 C14 C15 C16 119.18(17) . . . . ?
C13 C14 C15 C16 11.24(19) . . . . ?
C13 O6 C16 O7 178.7(2) . . . . ?
C13 O6 C16 C15 -1.5(2) . . . . ?
C14 C15 C16 O7 173.1(2) . . . . ?
C14 C15 C16 O6 -6.7(2) . . . . ?
O5 C13 C19 C20 -53.5(2) . . . . ?
O6 C13 C19 C20 63.3(2) . . . . ?
C14 C13 C19 C20 -177.34(16) . . . . ?

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.032

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a160909b
_audit_block_doi                 10.5517/ccdc.csd.cc1nk7l1
_database_code_depnum_ccdc_archive 'CCDC 1535913'
_audit_update_record             
;
2017-03-03 deposited with the CCDC.
2017-08-30 downloaded from the CCDC.
;
_audit_creation_date             2016-09-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H12 I2 O2'
_chemical_formula_sum            'C8 H12 I2 O2'
_chemical_formula_weight         393.98
_chemical_absolute_configuration ab
_chemical_melting_point          ?
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'
I I -0.4742 1.8119 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.2879(3)
_cell_length_b                   11.3154(5)
_cell_length_c                   13.6084(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1122.23(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2848
_cell_measurement_temperature    135.00(10)
_cell_measurement_theta_max      29.2370
_cell_measurement_theta_min      4.4490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.569
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4456
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         3.325
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      135.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     42.00  84.00   1.00    1.00    --   11.08-178.00 120.00   42
  2  ω     28.00  69.00   1.00    1.00    --   11.08  19.00-150.00   41
  3  ω     -4.00  84.00   1.00    1.00    --   11.08  38.00 -90.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0286749000
_diffrn_orient_matrix_UB_12      -0.0198832000
_diffrn_orient_matrix_UB_13      -0.0469846000
_diffrn_orient_matrix_UB_21      0.0179007000
_diffrn_orient_matrix_UB_22      -0.0568225000
_diffrn_orient_matrix_UB_23      0.0197701000
_diffrn_orient_matrix_UB_31      -0.0912998000
_diffrn_orient_matrix_UB_32      -0.0173810000
_diffrn_orient_matrix_UB_33      -0.0108956000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1904
_reflns_number_total             1981
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.020
_refine_diff_density_min         -0.988
_refine_diff_density_rms         0.206
_refine_ls_abs_structure_details 
;
 Flack x determined using 728 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_coef       0.0115(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1981
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0305
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0196P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0618
_refine_ls_wR_factor_ref         0.0634
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.26542(7) 0.86818(5) 0.98366(4) 0.0247(2) Uani 1 1 d . . . . .
I2 I 0.22233(9) 0.59202(5) 0.45537(4) 0.0254(2) Uani 1 1 d . . . . .
O1 O 0.4943(7) 0.8369(5) 0.7811(4) 0.0149(12) Uani 1 1 d . . . . .
O2 O 0.7782(8) 0.7662(5) 0.7649(4) 0.0212(13) Uani 1 1 d . . . . .
C1 C 0.3041(11) 0.7974(7) 0.7655(6) 0.0161(18) Uani 1 1 d . . . . .
C2 C 0.6153(10) 0.7516(7) 0.7546(6) 0.0145(18) Uani 1 1 d . . . . .
C3 C 0.5158(9) 0.6483(8) 0.7124(6) 0.0173(18) Uani 1 1 d . . . . .
H3A H 0.5060 0.5849 0.7601 0.021 Uiso 1 1 calc R . . . .
H3B H 0.5775 0.6188 0.6542 0.021 Uiso 1 1 calc R . . . .
C4 C 0.3281(10) 0.6978(7) 0.6871(6) 0.0160(18) Uani 1 1 d . . . . .
H4 H 0.3387 0.7364 0.6229 0.019 Uiso 1 1 calc R . . . .
C5 C 0.2317(12) 0.7490(6) 0.8611(5) 0.0205(18) Uani 1 1 d . . . . .
H5A H 0.2946 0.6755 0.8757 0.025 Uiso 1 1 calc R . . . .
H5B H 0.1023 0.7313 0.8534 0.025 Uiso 1 1 calc R . . . .
C6 C 0.1937(11) 0.9003(7) 0.7266(6) 0.0191(18) Uani 1 1 d . . . . .
H6A H 0.1872 0.9611 0.7757 0.029 Uiso 1 1 calc GR . . . .
H6B H 0.0720 0.8742 0.7106 0.029 Uiso 1 1 calc GR . . . .
H6C H 0.2518 0.9312 0.6687 0.029 Uiso 1 1 calc GR . . . .
C7 C 0.1742(11) 0.6083(7) 0.6795(6) 0.020(2) Uani 1 1 d . . . . .
H7A H 0.1601 0.5689 0.7424 0.024 Uiso 1 1 calc R . . . .
H7B H 0.0605 0.6494 0.6653 0.024 Uiso 1 1 calc R . . . .
C8 C 0.2070(11) 0.5162(6) 0.6008(5) 0.0175(17) Uani 1 1 d . . . . .
H8A H 0.1082 0.4587 0.6026 0.021 Uiso 1 1 calc R . . . .
H8B H 0.3206 0.4749 0.6149 0.021 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C5 2.159(7) . ?
I2 C8 2.161(7) . ?
O1 C1 1.472(9) . ?
O1 C2 1.356(9) . ?
O2 C2 1.207(9) . ?
C1 C4 1.562(11) . ?
C1 C5 1.507(10) . ?
C1 C6 1.511(11) . ?
C2 C3 1.491(11) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.518(10) . ?
C4 H4 0.9800 . ?
C4 C7 1.515(11) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.512(10) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?

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
C2 O1 C1 111.0(6) . . ?
O1 C1 C4 102.2(6) . . ?
O1 C1 C5 108.4(6) . . ?
O1 C1 C6 108.6(6) . . ?
C5 C1 C4 111.5(6) . . ?
C5 C1 C6 113.3(7) . . ?
C6 C1 C4 112.1(6) . . ?
O1 C2 C3 110.2(6) . . ?
O2 C2 O1 120.8(7) . . ?
O2 C2 C3 129.1(8) . . ?
C2 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
C2 C3 C4 103.7(6) . . ?
H3A C3 H3B 109.0 . . ?
C4 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
C1 C4 H4 107.2 . . ?
C3 C4 C1 102.2(6) . . ?
C3 C4 H4 107.2 . . ?
C7 C4 C1 116.5(6) . . ?
C7 C4 C3 115.8(7) . . ?
C7 C4 H4 107.2 . . ?
I1 C5 H5A 108.8 . . ?
I1 C5 H5B 108.8 . . ?
C1 C5 I1 113.6(5) . . ?
C1 C5 H5A 108.8 . . ?
C1 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.0 . . ?
C4 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 C4 113.1(7) . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
I2 C8 H8A 109.1 . . ?
I2 C8 H8B 109.1 . . ?
C7 C8 I2 112.5(5) . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?

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
O1 C1 C4 C3 31.5(7) . . . . ?
O1 C1 C4 C7 158.8(6) . . . . ?
O1 C1 C5 I1 52.1(8) . . . . ?
O1 C2 C3 C4 17.6(8) . . . . ?
O2 C2 C3 C4 -161.1(9) . . . . ?
C1 O1 C2 O2 -177.7(7) . . . . ?
C1 O1 C2 C3 3.4(8) . . . . ?
C1 C4 C7 C8 179.1(7) . . . . ?
C2 O1 C1 C4 -22.3(8) . . . . ?
C2 O1 C1 C5 95.6(7) . . . . ?
C2 O1 C1 C6 -140.9(6) . . . . ?
C2 C3 C4 C1 -29.7(8) . . . . ?
C2 C3 C4 C7 -157.5(6) . . . . ?
C3 C4 C7 C8 -60.6(9) . . . . ?
C4 C1 C5 I1 163.9(5) . . . . ?
C4 C7 C8 I2 -62.6(8) . . . . ?
C5 C1 C4 C3 -84.2(8) . . . . ?
C5 C1 C4 C7 43.2(9) . . . . ?
C6 C1 C4 C3 147.5(7) . . . . ?
C6 C1 C4 C7 -85.1(8) . . . . ?
C6 C1 C5 I1 -68.5(8) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-09-09
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.458
_oxdiff_exptl_absorpt_empirical_full_min 0.708
