# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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 
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# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_d19153
_audit_block_doi                 10.5517/ccdc.csd.cc24qnp7
_database_code_depnum_ccdc_archive 'CCDC 1987989'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/jacs.0c02513 2020
loop_
_audit_author_name
_audit_author_address
'Lawrence Henling'
;California Institute of Technology
United States of America
;
_audit_update_record             
;
2020-03-03 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;
_audit_creation_date             2019-12-22
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H26 O6'
_chemical_formula_sum            'C19 H26 O6'
_chemical_formula_weight         350.40
_chemical_absolute_configuration ad
_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'
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                   10.221(3)
_cell_length_b                   12.581(3)
_cell_length_c                   13.333(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1714.4(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9796
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      35.79
_cell_measurement_theta_min      2.51
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0554 before and 0.0509 after correction.
The Ratio of minimum to maximum transmission is 0.9208.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       lozenge
_exptl_crystal_F_000             752
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 0.00 0.1060
0.00 1.00 0.00 0.0860
0.00 0.00 -1.00 0.1540
-1.00 0.00 1.00 0.0690
1.00 0.00 -1.00 0.1300
1.00 0.00 1.00 0.1170
-1.00 0.00 -1.00 0.0990
-1.00 1.00 0.00 0.0410
1.00 -1.00 0.00 0.0910
-1.00 -1.00 0.00 0.0580
1.00 1.00 0.00 0.0900

_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            73152
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.285
_diffrn_reflns_theta_min         2.226
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CMOS Area Detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker PHOTON 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Triumph focusing graphite'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_type              'XRD C-TECH Long Fine Focus'
_diffrn_source_voltage           50.0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                6804
_reflns_number_total             7997
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       
'BIS 2018.9.0.2/05-Oct-2018 & APEX3_2018.7-2 (Bruker-AXS, 2018)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 2628 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.21(16)
_refine_ls_abs_structure_Hooft   0.26(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         7997
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.069
_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)+(0.0555P)²+0.1628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1007
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C5(H5), C6(H6A), C7(H7), C12(H12), C15(H15), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C11(H11A,H11B), C14(H14A,H14B), C16(H16A,H16B), C18(H18A,H18B)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C19(H19A,H19B,H19C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4), O6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O1 O 0.68042(10) 0.78131(7) 0.63641(8) 0.01648(18) Uani 1 1 d . . . . .
H1 H 0.668382 0.847062 0.630576 0.025 Uiso 1 1 calc R U . . .
O2 O 0.86227(11) 0.70321(8) 0.47229(8) 0.0213(2) Uani 1 1 d . . . . .
O3 O 0.70632(11) 0.61684(9) 0.39054(7) 0.0213(2) Uani 1 1 d . . . . .
O4 O 0.52317(11) 0.47286(8) 0.43910(8) 0.0209(2) Uani 1 1 d . . . . .
H4 H 0.578439 0.516972 0.418089 0.031 Uiso 1 1 calc R U . . .
O5 O 0.62828(10) 0.58461(8) 0.81516(7) 0.01697(19) Uani 1 1 d . . . . .
O6 O 0.61450(11) -0.00568(7) 0.63049(8) 0.0186(2) Uani 1 1 d . . . . .
H6 H 0.542330 0.010339 0.656580 0.028 Uiso 1 1 calc R U . . .
C1 C 0.80656(12) 0.63996(9) 0.70998(9) 0.0120(2) Uani 1 1 d . . . . .
H1A H 0.860316 0.628346 0.771685 0.014 Uiso 1 1 calc R U . . .
C2 C 0.79658(13) 0.76259(9) 0.69319(10) 0.0142(2) Uani 1 1 d . . . . .
C3 C 0.79192(15) 0.82417(10) 0.79130(11) 0.0201(3) Uani 1 1 d . . . . .
H3A H 0.778922 0.899866 0.777118 0.030 Uiso 1 1 calc R U . . .
H3B H 0.874474 0.814429 0.827536 0.030 Uiso 1 1 calc R U . . .
H3C H 0.719358 0.797886 0.832450 0.030 Uiso 1 1 calc R U . . .
C4 C 0.91843(14) 0.78776(11) 0.63116(11) 0.0195(3) Uani 1 1 d . . . . .
H4A H 0.904607 0.852900 0.590884 0.023 Uiso 1 1 calc R U . . .
H4B H 0.994845 0.798930 0.675557 0.023 Uiso 1 1 calc R U . . .
C5 C 0.94105(14) 0.69305(11) 0.56324(11) 0.0193(3) Uani 1 1 d . . . . .
H5 H 1.035958 0.684266 0.547008 0.023 Uiso 1 1 calc R U . . .
C6 C 0.88652(12) 0.59459(10) 0.61866(9) 0.0136(2) Uani 1 1 d . . . . .
H6A H 0.960648 0.550141 0.643917 0.016 Uiso 1 1 calc R U . . .
C7 C 0.81180(12) 0.53340(10) 0.53598(9) 0.0136(2) Uani 1 1 d . . . . .
H7 H 0.871429 0.479118 0.505763 0.016 Uiso 1 1 calc R U . . .
C8 C 0.78429(13) 0.61948(11) 0.45872(10) 0.0170(2) Uani 1 1 d . . . . .
C9 C 0.69363(12) 0.47732(9) 0.58110(9) 0.01159(19) Uani 1 1 d . . . . .
C10 C 0.56514(13) 0.43122(10) 0.53164(10) 0.0139(2) Uani 1 1 d . . . . .
C11 C 0.48826(13) 0.48194(11) 0.62174(10) 0.0181(2) Uani 1 1 d . . . . .
H11A H 0.406323 0.518292 0.601949 0.022 Uiso 1 1 calc R U . . .
H11B H 0.473227 0.432626 0.678441 0.022 Uiso 1 1 calc R U . . .
C12 C 0.60524(12) 0.55734(9) 0.63681(9) 0.0124(2) Uani 1 1 d . . . . .
H12 H 0.592429 0.620644 0.592527 0.015 Uiso 1 1 calc R U . . .
C13 C 0.67102(12) 0.59314(9) 0.72997(9) 0.0118(2) Uani 1 1 d . . . . .
C14 C 0.73647(13) 0.38142(9) 0.64645(9) 0.0139(2) Uani 1 1 d . . . . .
H14A H 0.831547 0.384520 0.660333 0.017 Uiso 1 1 calc R U . . .
H14B H 0.688744 0.381248 0.711066 0.017 Uiso 1 1 calc R U . . .
C15 C 0.70260(13) 0.28115(9) 0.58468(9) 0.0131(2) Uani 1 1 d . . . . .
H15 H 0.772947 0.269571 0.533703 0.016 Uiso 1 1 calc R U . . .
C16 C 0.57444(15) 0.31051(10) 0.52945(11) 0.0187(3) Uani 1 1 d . . . . .
H16A H 0.576806 0.284508 0.459387 0.022 Uiso 1 1 calc R U . . .
H16B H 0.498163 0.278372 0.563717 0.022 Uiso 1 1 calc R U . . .
C17 C 0.68816(13) 0.17984(9) 0.64757(9) 0.0127(2) Uani 1 1 d . . . . .
H17 H 0.608075 0.188135 0.689944 0.015 Uiso 1 1 calc R U . . .
C18 C 0.66587(14) 0.08454(10) 0.57824(10) 0.0159(2) Uani 1 1 d . . . . .
H18A H 0.604222 0.105171 0.524377 0.019 Uiso 1 1 calc R U . . .
H18B H 0.749881 0.064731 0.546355 0.019 Uiso 1 1 calc R U . . .
C19 C 0.80353(15) 0.15980(10) 0.71809(10) 0.0181(2) Uani 1 1 d . . . . .
H19A H 0.791251 0.091706 0.752509 0.027 Uiso 1 1 calc R U . . .
H19B H 0.808414 0.217106 0.767733 0.027 Uiso 1 1 calc R U . . .
H19C H 0.884867 0.157756 0.679213 0.027 Uiso 1 1 calc R U . . .


_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 H1 0.8400 . ?
O1 C2 1.4276(16) . ?
O2 C5 1.4612(19) . ?
O2 C8 1.3333(18) . ?
O3 C8 1.2094(17) . ?
O4 H4 0.8400 . ?
O4 C10 1.4075(16) . ?
O5 C13 1.2217(15) . ?
O6 H6 0.8400 . ?
O6 C18 1.4316(16) . ?
C1 H1A 1.0000 . ?
C1 C2 1.5623(17) . ?
C1 C6 1.5736(18) . ?
C1 C13 1.5287(18) . ?
C2 C3 1.5210(19) . ?
C2 C4 1.528(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.514(2) . ?
C5 H5 1.0000 . ?
C5 C6 1.5463(18) . ?
C6 H6A 1.0000 . ?
C6 C7 1.5464(18) . ?
C7 H7 1.0000 . ?
C7 C8 1.5209(17) . ?
C7 C9 1.5227(17) . ?
C9 C10 1.5799(18) . ?
C9 C12 1.5432(16) . ?
C9 C14 1.5513(17) . ?
C10 C11 1.5708(19) . ?
C10 C16 1.5219(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.5394(18) . ?
C12 H12 1.0000 . ?
C12 C13 1.4825(17) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5459(17) . ?
C15 H15 1.0000 . ?
C15 C16 1.5474(19) . ?
C15 C17 1.5328(17) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17 1.0000 . ?
C17 C18 1.5310(17) . ?
C17 C19 1.5290(19) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C2 O1 H1 109.5 . . ?
C8 O2 C5 111.89(10) . . ?
C10 O4 H4 109.5 . . ?
C18 O6 H6 109.5 . . ?
C2 C1 H1A 107.3 . . ?
C2 C1 C6 106.34(10) . . ?
C6 C1 H1A 107.3 . . ?
C13 C1 H1A 107.3 . . ?
C13 C1 C2 110.27(10) . . ?
C13 C1 C6 117.76(10) . . ?
O1 C2 C1 107.05(10) . . ?
O1 C2 C3 110.24(11) . . ?
O1 C2 C4 110.89(11) . . ?
C3 C2 C1 112.44(10) . . ?
C3 C2 C4 112.67(11) . . ?
C4 C2 C1 103.24(10) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 110.4 . . ?
C2 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
C5 C4 C2 106.56(11) . . ?
C5 C4 H4A 110.4 . . ?
C5 C4 H4B 110.4 . . ?
O2 C5 C4 110.08(12) . . ?
O2 C5 H5 111.4 . . ?
O2 C5 C6 105.55(11) . . ?
C4 C5 H5 111.4 . . ?
C4 C5 C6 106.83(11) . . ?
C6 C5 H5 111.4 . . ?
C1 C6 H6A 109.6 . . ?
C5 C6 C1 105.44(10) . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 C7 103.66(10) . . ?
C7 C6 C1 118.41(10) . . ?
C7 C6 H6A 109.6 . . ?
C6 C7 H7 109.0 . . ?
C8 C7 C6 102.68(10) . . ?
C8 C7 H7 109.0 . . ?
C8 C7 C9 116.80(11) . . ?
C9 C7 C6 109.92(10) . . ?
C9 C7 H7 109.0 . . ?
O2 C8 C7 111.12(11) . . ?
O3 C8 O2 121.17(12) . . ?
O3 C8 C7 127.68(13) . . ?
C7 C9 C10 131.65(10) . . ?
C7 C9 C12 110.62(9) . . ?
C7 C9 C14 111.00(10) . . ?
C12 C9 C10 87.35(9) . . ?
C12 C9 C14 113.72(10) . . ?
C14 C9 C10 100.58(9) . . ?
O4 C10 C9 118.85(11) . . ?
O4 C10 C11 111.51(11) . . ?
O4 C10 C16 111.94(11) . . ?
C11 C10 C9 86.99(9) . . ?
C16 C10 C9 108.81(10) . . ?
C16 C10 C11 116.83(12) . . ?
C10 C11 H11A 114.0 . . ?
C10 C11 H11B 114.0 . . ?
H11A C11 H11B 111.2 . . ?
C12 C11 C10 87.80(10) . . ?
C12 C11 H11A 114.0 . . ?
C12 C11 H11B 114.0 . . ?
C9 C12 H12 108.2 . . ?
C11 C12 C9 89.41(9) . . ?
C11 C12 H12 108.2 . . ?
C13 C12 C9 109.63(10) . . ?
C13 C12 C11 130.45(11) . . ?
C13 C12 H12 108.2 . . ?
O5 C13 C1 121.33(11) . . ?
O5 C13 C12 126.17(12) . . ?
C12 C13 C1 112.45(10) . . ?
C9 C14 H14A 110.6 . . ?
C9 C14 H14B 110.6 . . ?
H14A C14 H14B 108.7 . . ?
C15 C14 C9 105.80(9) . . ?
C15 C14 H14A 110.6 . . ?
C15 C14 H14B 110.6 . . ?
C14 C15 H15 108.7 . . ?
C14 C15 C16 104.37(10) . . ?
C16 C15 H15 108.7 . . ?
C17 C15 C14 114.12(10) . . ?
C17 C15 H15 108.7 . . ?
C17 C15 C16 112.17(11) . . ?
C10 C16 C15 106.38(11) . . ?
C10 C16 H16A 110.5 . . ?
C10 C16 H16B 110.5 . . ?
C15 C16 H16A 110.5 . . ?
C15 C16 H16B 110.5 . . ?
H16A C16 H16B 108.6 . . ?
C15 C17 H17 107.5 . . ?
C18 C17 C15 109.58(10) . . ?
C18 C17 H17 107.5 . . ?
C19 C17 C15 113.53(11) . . ?
C19 C17 H17 107.5 . . ?
C19 C17 C18 110.91(10) . . ?
O6 C18 C17 112.44(10) . . ?
O6 C18 H18A 109.1 . . ?
O6 C18 H18B 109.1 . . ?
C17 C18 H18A 109.1 . . ?
C17 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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
_geom_hbond_publ_flag
O1 H1 O6 0.84 1.93 2.7645(15) 170.3 1_565 yes
O4 H4 O3 0.84 1.85 2.6841(17) 172.0 . yes
O6 H6 O5 0.84 2.01 2.8235(16) 161.6 3_646 yes

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 C2 C4 C5 -79.58(13) . . . . ?
O2 C5 C6 C1 -105.80(11) . . . . ?
O2 C5 C6 C7 19.30(13) . . . . ?
O4 C10 C11 C12 -98.40(12) . . . . ?
O4 C10 C16 C15 137.74(11) . . . . ?
C1 C2 C4 C5 34.76(13) . . . . ?
C1 C6 C7 C8 94.36(12) . . . . ?
C1 C6 C7 C9 -30.62(14) . . . . ?
C2 C1 C6 C5 9.99(13) . . . . ?
C2 C1 C6 C7 -105.35(12) . . . . ?
C2 C1 C13 O5 -91.19(14) . . . . ?
C2 C1 C13 C12 91.19(12) . . . . ?
C2 C4 C5 O2 84.92(13) . . . . ?
C2 C4 C5 C6 -29.20(14) . . . . ?
C3 C2 C4 C5 156.31(11) . . . . ?
C4 C5 C6 C1 11.36(14) . . . . ?
C4 C5 C6 C7 136.46(11) . . . . ?
C5 O2 C8 O3 175.54(12) . . . . ?
C5 O2 C8 C7 -6.18(15) . . . . ?
C5 C6 C7 C8 -21.94(12) . . . . ?
C5 C6 C7 C9 -146.91(10) . . . . ?
C6 C1 C2 O1 89.94(12) . . . . ?
C6 C1 C2 C3 -148.85(11) . . . . ?
C6 C1 C2 C4 -27.15(13) . . . . ?
C6 C1 C13 O5 146.60(12) . . . . ?
C6 C1 C13 C12 -31.03(14) . . . . ?
C6 C7 C8 O2 18.23(13) . . . . ?
C6 C7 C8 O3 -163.63(13) . . . . ?
C6 C7 C9 C10 161.05(11) . . . . ?
C6 C7 C9 C12 55.47(12) . . . . ?
C6 C7 C9 C14 -71.76(12) . . . . ?
C7 C9 C10 O4 -24.01(18) . . . . ?
C7 C9 C10 C11 -136.98(13) . . . . ?
C7 C9 C10 C16 105.66(14) . . . . ?
C7 C9 C12 C11 155.80(10) . . . . ?
C7 C9 C12 C13 -70.95(12) . . . . ?
C7 C9 C14 C15 -106.00(11) . . . . ?
C8 O2 C5 C4 -123.70(12) . . . . ?
C8 O2 C5 C6 -8.76(15) . . . . ?
C8 C7 C9 C10 44.64(17) . . . . ?
C8 C7 C9 C12 -60.94(14) . . . . ?
C8 C7 C9 C14 171.83(10) . . . . ?
C9 C7 C8 O2 138.56(11) . . . . ?
C9 C7 C8 O3 -43.30(18) . . . . ?
C9 C10 C11 C12 21.52(9) . . . . ?
C9 C10 C16 C15 4.37(15) . . . . ?
C9 C12 C13 O5 -121.85(13) . . . . ?
C9 C12 C13 C1 55.64(13) . . . . ?
C9 C14 C15 C16 -35.43(13) . . . . ?
C9 C14 C15 C17 -158.22(11) . . . . ?
C10 C9 C12 C11 21.90(9) . . . . ?
C10 C9 C12 C13 155.15(10) . . . . ?
C10 C9 C14 C15 36.73(12) . . . . ?
C10 C11 C12 C9 -22.02(9) . . . . ?
C10 C11 C12 C13 -137.67(13) . . . . ?
C11 C10 C16 C15 -91.96(14) . . . . ?
C11 C12 C13 O5 -15.0(2) . . . . ?
C11 C12 C13 C1 162.49(12) . . . . ?
C12 C9 C10 O4 91.51(12) . . . . ?
C12 C9 C10 C11 -21.47(9) . . . . ?
C12 C9 C10 C16 -138.83(11) . . . . ?
C12 C9 C14 C15 128.49(11) . . . . ?
C13 C1 C2 O1 -38.79(13) . . . . ?
C13 C1 C2 C3 82.43(13) . . . . ?
C13 C1 C2 C4 -155.87(10) . . . . ?
C13 C1 C6 C5 134.19(11) . . . . ?
C13 C1 C6 C7 18.86(15) . . . . ?
C14 C9 C10 O4 -154.85(11) . . . . ?
C14 C9 C10 C11 92.17(10) . . . . ?
C14 C9 C10 C16 -25.19(13) . . . . ?
C14 C9 C12 C11 -78.49(12) . . . . ?
C14 C9 C12 C13 54.76(13) . . . . ?
C14 C15 C16 C10 18.65(14) . . . . ?
C14 C15 C17 C18 -175.42(11) . . . . ?
C14 C15 C17 C19 -50.80(15) . . . . ?
C15 C17 C18 O6 -163.03(11) . . . . ?
C16 C10 C11 C12 131.10(12) . . . . ?
C16 C15 C17 C18 66.15(14) . . . . ?
C16 C15 C17 C19 -169.23(11) . . . . ?
C17 C15 C16 C10 142.70(11) . . . . ?
C19 C17 C18 O6 70.85(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_v20001
_database_code_depnum_ccdc_archive 'CCDC 2239966'
loop_
_audit_author_name
_audit_author_address
'Michael Takase'
;California Institute of Technology
United States of America
;
_audit_update_record             
;
2023-02-05 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;
_audit_creation_date             2020-01-25
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003),
 SHELXL-2018/3, and manual edit
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 N O4'
_chemical_formula_sum            'C20 H21 N O4'
_chemical_formula_weight         339.38
_chemical_absolute_configuration ad
_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 0.0181 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'
N N 0.0311 0.0180 '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'

_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.105(2)
_cell_length_b                   8.9547(18)
_cell_length_c                   10.215(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.038(10)
_cell_angle_gamma                90
_cell_volume                     868.4(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9767
_cell_measurement_temperature    100
_cell_measurement_theta_max      79.73
_cell_measurement_theta_min      4.66
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.804
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1251 before and 0.0764 after correction.
The Ratio of minimum to maximum transmission is 0.8859.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       blade
_exptl_crystal_F_000             360
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 0.00 0.00 0.0040
-1.00 0.00 0.00 0.0100
0.00 -1.00 0.00 0.1550
0.00 1.00 0.00 0.1090
0.00 0.00 1.00 0.0220
0.00 0.00 -1.00 0.0080
-1.00 1.00 1.00 0.0830

_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15034
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.944
_diffrn_reflns_theta_min         4.607
_diffrn_ambient_temperature      100
_diffrn_detector                 'CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.69
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\mS HB'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.936
_reflns_number_gt                3419
_reflns_number_total             3650
_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.

 The final difference map exhibits 4 small positive excursions
near the isopropenyl group. These represent some disorder or
impurity and were not interpreted.

 Electron density synthesis with coefficients Fo-Fc
 Highest peak    0.70  at  0.9655  0.2573  0.1381  [  0.86 A from H18B ]
 Deepest hole   -0.20  at  0.6749  0.3922  0.2642  [  1.39 A from C2 ]

 Fourier peaks appended to .res file
              x       y       z       sof     U      Peak   Distances to nearest atoms (including eq.)

 Q1    1   1.0345  0.7573  0.8619   1.00000  0.05    0.70   0.86 H18B^a  0.93 C18  1.06 H18A  2.24 C16
 Q2    1   0.9081  0.4626  1.0008   1.00000  0.05    0.46   0.57 H17B^a  1.52 C17  1.96 H17C^a  2.08 H17A
 Q3    1   0.9850  0.3350  0.9226   1.00000  0.05    0.32   0.96 H17C^a  1.56 C17  1.62 H17B^a  2.21 H18A
 Q4    1   1.0199  0.5503  0.8257   1.00000  0.05    0.31   1.04 C18  1.12 C16  1.44 H18A  1.75 H18B^a
 Q5    1   0.6749  0.3922  0.2642   1.00000  0.05   -0.20   1.39 C2  1.42 C1  1.45 C3  1.49 C8
 Q6    1   0.8692  0.4769  0.7626   1.00000  0.05    0.20   0.80 C16  0.94 C17  1.40 H17C^a  1.42 H17A
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       
'BIS V6.2.9/2018-03-16 & APEX3 v2018.7-2 (Bruker-AXS, 2018)'
_computing_cell_refinement       'SAINT V8.40A (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.40A (Bruker-AXS, 2016)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND 3 (Crystal Impact, 1999)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_refine_diff_density_max         0.703
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1452 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(10)
_refine_ls_abs_structure_Hooft   0.14(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3650
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.074
_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)+(0.0457P)²+0.3625P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1048
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C11(H11A,H11B), C13(H13A,H13B), C20(H20A,H20B)
2.c X=CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
O1 O 0.6691(2) 0.5925(2) 0.0780(2) 0.0315(5) Uani 1 1 d . . . A 1
O2 O 0.5021(2) 0.5006(2) 0.3358(2) 0.0247(4) Uani 1 1 d . . . A 1
H2 H 0.442415 0.533902 0.368705 0.037 Uiso 1 1 calc R U . A 1
O3 O 0.5217(2) 0.1146(2) 0.3785(2) 0.0260(5) Uani 1 1 d . . . A 1
O4 O 0.7182(2) 0.1082(2) 0.5628(2) 0.0291(5) Uani 1 1 d . . . A 1
N1 N 0.6896(3) 0.8901(3) 0.2463(3) 0.0370(7) Uani 1 1 d . . . A 1
C1 C 0.7848(3) 0.4993(3) 0.3049(3) 0.0180(5) Uani 1 1 d . . . A 1
C2 C 0.6663(3) 0.5022(3) 0.1655(3) 0.0203(5) Uani 1 1 d . . . A 1
C3 C 0.5485(3) 0.3912(3) 0.1411(3) 0.0183(5) Uani 1 1 d . . . A 1
H3 H 0.504099 0.374378 0.038510 0.022 Uiso 1 1 calc R U . A 1
C4 C 0.4315(3) 0.4410(3) 0.1997(3) 0.0224(6) Uani 1 1 d . . . A 1
C5 C 0.3601(3) 0.2917(3) 0.2090(3) 0.0259(6) Uani 1 1 d . . . A 1
H5A H 0.321815 0.294627 0.286068 0.031 Uiso 1 1 calc R U . A 1
H5B H 0.281618 0.272105 0.120929 0.031 Uiso 1 1 calc R U . A 1
C6 C 0.4718(3) 0.1690(3) 0.2352(3) 0.0223(6) Uani 1 1 d . . . A 1
H6 H 0.435261 0.084259 0.168906 0.027 Uiso 1 1 calc R U . A 1
C7 C 0.6000(3) 0.2412(3) 0.2115(3) 0.0191(5) Uani 1 1 d . . . A 1
H7 H 0.638700 0.176342 0.153464 0.023 Uiso 1 1 calc R U . A 1
C8 C 0.7021(3) 0.2586(3) 0.3568(3) 0.0179(5) Uani 1 1 d . . . A 1
C9 C 0.6566(3) 0.1536(3) 0.4455(3) 0.0219(6) Uani 1 1 d . . . A 1
C10 C 0.7881(3) 0.3752(3) 0.4033(3) 0.0179(5) Uani 1 1 d . . . A 1
C11 C 0.8769(3) 0.3988(3) 0.5528(3) 0.0204(5) Uani 1 1 d . . . A 1
H11A H 0.977569 0.401552 0.561745 0.025 Uiso 1 1 calc R U . A 1
H11B H 0.863205 0.314512 0.609622 0.025 Uiso 1 1 calc R U . A 1
C12 C 0.8368(3) 0.5460(3) 0.6072(3) 0.0216(5) Uani 1 1 d . . . A 1
H12 H 0.732296 0.547001 0.584104 0.026 Uiso 1 1 calc R U . A 1
C13 C 0.8759(3) 0.6762(3) 0.5310(3) 0.0237(6) Uani 1 1 d . . . A 1
H13A H 0.979501 0.688614 0.566957 0.028 Uiso 1 1 calc R U . A 1
H13B H 0.833838 0.768866 0.552343 0.028 Uiso 1 1 calc R U . A 1
C14 C 0.8270(3) 0.6566(3) 0.3722(3) 0.0205(5) Uani 1 1 d . . . A 1
C15 C 0.3319(3) 0.5557(4) 0.1090(3) 0.0320(7) Uani 1 1 d . . . A 1
H15A H 0.255881 0.575623 0.145752 0.048 Uiso 1 1 calc R U . A 1
H15B H 0.291865 0.517453 0.013640 0.048 Uiso 1 1 calc R U . A 1
H15C H 0.383494 0.648351 0.108925 0.048 Uiso 1 1 calc R U . A 1
C16 C 0.9050(3) 0.5567(4) 0.7640(3) 0.0290(7) Uani 1 1 d . . . A 1
C17 C 0.8592(5) 0.4393(4) 0.8444(4) 0.0441(9) Uani 1 1 d . . . A 1
H17A H 0.756674 0.427422 0.805241 0.066 Uiso 1 1 calc R U . A 1
H17B H 0.886236 0.469625 0.942304 0.066 Uiso 1 1 calc R U . A 1
H17C H 0.904719 0.344223 0.838278 0.066 Uiso 1 1 calc R U . A 1
C18 C 0.9980(4) 0.6633(5) 0.8294(4) 0.0401(8) Uani 1 1 d . . . A 1
H18A H 1.035911 0.665283 0.928308 0.048 Uiso 1 1 calc R U . A 1
H18B H 1.025653 0.736617 0.776689 0.048 Uiso 1 1 calc R U . A 1
C19 C 0.7478(3) 0.7838(3) 0.2970(3) 0.0250(6) Uani 1 1 d . . . A 1
C20 C 0.9192(3) 0.5758(3) 0.3063(3) 0.0235(6) Uani 1 1 d . . . A 1
H20A H 1.009572 0.534714 0.369183 0.028 Uiso 1 1 calc R U . A 1
H20B H 0.922254 0.614911 0.216751 0.028 Uiso 1 1 calc R U . A 1


_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 C2 1.213(3) . ?
O2 H2 0.8400 . ?
O2 C4 1.430(3) . ?
O3 C6 1.459(3) . ?
O3 C9 1.345(3) . ?
O4 C9 1.215(3) . ?
N1 C19 1.146(4) . ?
C1 C2 1.514(4) . ?
C1 C10 1.491(4) . ?
C1 C14 1.562(4) . ?
C1 C20 1.517(4) . ?
C2 C3 1.505(4) . ?
C3 H3 1.0000 . ?
C3 C4 1.562(4) . ?
C3 C7 1.528(4) . ?
C4 C5 1.537(4) . ?
C4 C15 1.512(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.531(4) . ?
C6 H6 1.0000 . ?
C6 C7 1.539(4) . ?
C7 H7 1.0000 . ?
C7 C8 1.498(4) . ?
C8 C9 1.484(4) . ?
C8 C10 1.338(4) . ?
C10 C11 1.497(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.538(4) . ?
C12 H12 1.0000 . ?
C12 C13 1.527(4) . ?
C12 C16 1.515(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.535(4) . ?
C14 C19 1.451(4) . ?
C14 C20 1.508(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.502(5) . ?
C16 C18 1.345(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9500 . ?
C18 H18B 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?

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
C4 O2 H2 109.5 . . ?
C9 O3 C6 111.4(2) . . ?
C2 C1 C14 114.0(2) . . ?
C2 C1 C20 114.7(2) . . ?
C10 C1 C2 118.4(2) . . ?
C10 C1 C14 115.8(2) . . ?
C10 C1 C20 121.1(2) . . ?
C20 C1 C14 58.64(17) . . ?
O1 C2 C1 119.6(2) . . ?
O1 C2 C3 122.4(2) . . ?
C3 C2 C1 118.0(2) . . ?
C2 C3 H3 108.6 . . ?
C2 C3 C4 114.1(2) . . ?
C2 C3 C7 112.3(2) . . ?
C4 C3 H3 108.6 . . ?
C7 C3 H3 108.6 . . ?
C7 C3 C4 104.5(2) . . ?
O2 C4 C3 106.7(2) . . ?
O2 C4 C5 110.7(2) . . ?
O2 C4 C15 110.4(2) . . ?
C5 C4 C3 102.0(2) . . ?
C15 C4 C3 113.0(2) . . ?
C15 C4 C5 113.6(2) . . ?
C4 C5 H5A 110.2 . . ?
C4 C5 H5B 110.2 . . ?
H5A C5 H5B 108.5 . . ?
C6 C5 C4 107.6(2) . . ?
C6 C5 H5A 110.2 . . ?
C6 C5 H5B 110.2 . . ?
O3 C6 C5 113.3(2) . . ?
O3 C6 H6 110.3 . . ?
O3 C6 C7 106.2(2) . . ?
C5 C6 H6 110.3 . . ?
C5 C6 C7 106.3(2) . . ?
C7 C6 H6 110.3 . . ?
C3 C7 C6 105.9(2) . . ?
C3 C7 H7 111.8 . . ?
C6 C7 H7 111.8 . . ?
C8 C7 C3 112.5(2) . . ?
C8 C7 C6 102.6(2) . . ?
C8 C7 H7 111.8 . . ?
C9 C8 C7 106.7(2) . . ?
C10 C8 C7 125.2(2) . . ?
C10 C8 C9 125.3(2) . . ?
O3 C9 C8 109.0(2) . . ?
O4 C9 O3 120.2(2) . . ?
O4 C9 C8 130.7(3) . . ?
C1 C10 C11 116.8(2) . . ?
C8 C10 C1 118.7(2) . . ?
C8 C10 C11 124.2(2) . . ?
C10 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
C10 C11 C12 110.4(2) . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C11 C12 H12 108.1 . . ?
C13 C12 C11 108.9(2) . . ?
C13 C12 H12 108.1 . . ?
C16 C12 C11 110.8(2) . . ?
C16 C12 H12 108.1 . . ?
C16 C12 C13 112.8(2) . . ?
C12 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
C12 C13 C14 113.9(2) . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C13 C14 C1 120.6(2) . . ?
C19 C14 C1 117.2(2) . . ?
C19 C14 C13 112.9(2) . . ?
C19 C14 C20 116.9(2) . . ?
C20 C14 C1 59.19(17) . . ?
C20 C14 C13 120.1(2) . . ?
C4 C15 H15A 109.5 . . ?
C4 C15 H15B 109.5 . . ?
C4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C12 114.9(3) . . ?
C18 C16 C12 123.9(3) . . ?
C18 C16 C17 121.3(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 120.0 . . ?
C16 C18 H18B 120.0 . . ?
H18A C18 H18B 120.0 . . ?
N1 C19 C14 175.0(3) . . ?
C1 C20 H20A 117.5 . . ?
C1 C20 H20B 117.5 . . ?
C14 C20 C1 62.17(18) . . ?
C14 C20 H20A 117.5 . . ?
C14 C20 H20B 117.5 . . ?
H20A C20 H20B 114.6 . . ?

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
_geom_hbond_publ_flag
O2 H2 O3 0.84 2.58 3.178(3) 128.7 2_656 yes
O2 H2 O4 0.84 2.08 2.923(3) 175.4 2_656 yes
C6 H6 O1 1.00 2.38 3.100(3) 128.4 2_645 yes
C11 H11B O4 0.99 2.30 3.077(3) 134.1 . yes

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 C2 C3 C4 -96.4(3) . . . . ?
O1 C2 C3 C7 144.8(3) . . . . ?
O2 C4 C5 C6 -83.4(3) . . . . ?
O3 C6 C7 C3 -133.3(2) . . . . ?
O3 C6 C7 C8 -15.2(3) . . . . ?
C1 C2 C3 C4 83.7(3) . . . . ?
C1 C2 C3 C7 -35.1(3) . . . . ?
C1 C10 C11 C12 53.3(3) . . . . ?
C2 C1 C10 C8 11.3(4) . . . . ?
C2 C1 C10 C11 -161.9(2) . . . . ?
C2 C1 C14 C13 145.6(2) . . . . ?
C2 C1 C14 C19 1.3(4) . . . . ?
C2 C1 C14 C20 -105.3(3) . . . . ?
C2 C1 C20 C14 104.1(2) . . . . ?
C2 C3 C4 O2 -44.1(3) . . . . ?
C2 C3 C4 C5 -160.3(2) . . . . ?
C2 C3 C4 C15 77.4(3) . . . . ?
C2 C3 C7 C6 155.2(2) . . . . ?
C2 C3 C7 C8 43.9(3) . . . . ?
C3 C4 C5 C6 29.8(3) . . . . ?
C3 C7 C8 C9 133.3(2) . . . . ?
C3 C7 C8 C10 -28.3(4) . . . . ?
C4 C3 C7 C6 31.0(3) . . . . ?
C4 C3 C7 C8 -80.3(3) . . . . ?
C4 C5 C6 O3 104.8(3) . . . . ?
C4 C5 C6 C7 -11.4(3) . . . . ?
C5 C6 C7 C3 -12.4(3) . . . . ?
C5 C6 C7 C8 105.7(2) . . . . ?
C6 O3 C9 O4 -174.6(3) . . . . ?
C6 O3 C9 C8 8.5(3) . . . . ?
C6 C7 C8 C9 20.0(3) . . . . ?
C6 C7 C8 C10 -141.7(3) . . . . ?
C7 C3 C4 O2 79.0(3) . . . . ?
C7 C3 C4 C5 -37.2(3) . . . . ?
C7 C3 C4 C15 -159.6(2) . . . . ?
C7 C8 C9 O3 -18.6(3) . . . . ?
C7 C8 C9 O4 165.0(3) . . . . ?
C7 C8 C10 C1 -0.2(4) . . . . ?
C7 C8 C10 C11 172.5(2) . . . . ?
C8 C10 C11 C12 -119.5(3) . . . . ?
C9 O3 C6 C5 -111.7(3) . . . . ?
C9 O3 C6 C7 4.6(3) . . . . ?
C9 C8 C10 C1 -158.5(2) . . . . ?
C9 C8 C10 C11 14.1(4) . . . . ?
C10 C1 C2 O1 -172.3(3) . . . . ?
C10 C1 C2 C3 7.6(4) . . . . ?
C10 C1 C14 C13 3.1(4) . . . . ?
C10 C1 C14 C19 -141.2(2) . . . . ?
C10 C1 C14 C20 112.2(3) . . . . ?
C10 C1 C20 C14 -103.2(3) . . . . ?
C10 C8 C9 O3 143.1(3) . . . . ?
C10 C8 C9 O4 -33.3(5) . . . . ?
C10 C11 C12 C13 -66.3(3) . . . . ?
C10 C11 C12 C16 169.1(2) . . . . ?
C11 C12 C13 C14 47.7(3) . . . . ?
C11 C12 C16 C17 -63.1(3) . . . . ?
C11 C12 C16 C18 118.0(3) . . . . ?
C12 C13 C14 C1 -17.6(4) . . . . ?
C12 C13 C14 C19 128.1(3) . . . . ?
C12 C13 C14 C20 -87.5(3) . . . . ?
C13 C12 C16 C17 174.5(3) . . . . ?
C13 C12 C16 C18 -4.4(4) . . . . ?
C13 C14 C20 C1 109.8(3) . . . . ?
C14 C1 C2 O1 46.2(4) . . . . ?
C14 C1 C2 C3 -133.9(2) . . . . ?
C14 C1 C10 C8 152.1(2) . . . . ?
C14 C1 C10 C11 -21.1(3) . . . . ?
C15 C4 C5 C6 151.7(2) . . . . ?
C16 C12 C13 C14 171.2(2) . . . . ?
C19 C14 C20 C1 -107.1(3) . . . . ?
C20 C1 C2 O1 -18.8(4) . . . . ?
C20 C1 C2 C3 161.1(2) . . . . ?
C20 C1 C10 C8 -140.4(3) . . . . ?
C20 C1 C10 C11 46.4(3) . . . . ?
C20 C1 C14 C13 -109.1(3) . . . . ?
C20 C1 C14 C19 106.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_v18612
_database_code_depnum_ccdc_archive 'CCDC 2239957'
loop_
_audit_author_name
_audit_author_address
'Michael Takase'
;California Institute of Technology
United States of America
;
_audit_update_record             
;
2023-02-05 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;
_audit_creation_date             2019-01-15
# start Validation Reply Form
_vrf_PLAT340_v18612              
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01464 Ang.  
RESPONSE: The crystals were small, not of good quality, and were not single.
Multiple crystals were examined. Various integrations as a twin and
single component crystal were done.
;
# end Validation Reply Form
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
,
 SHELXL-2017/1, and manual edit
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H19 Cl O5, 0.5(H2 O), 0.09(C2 H2 Cl6)'
_chemical_formula_sum            'C16.19 H20.19 Cl1.59 O5.50'
_chemical_formula_weight         359.09
_chemical_absolute_configuration ad
_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 0.0181 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'
Cl Cl 0.3639 0.7018 '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'

_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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   34.102(5)
_cell_length_b                   14.485(2)
_cell_length_c                   6.6087(11)
_cell_angle_alpha                90
_cell_angle_beta                 94.960(10)
_cell_angle_gamma                90
_cell_volume                     3252.2(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9939
_cell_measurement_temperature    100
_cell_measurement_theta_max      74.72
_cell_measurement_theta_min      3.32
_shelx_estimated_absorpt_T_max   0.910
_shelx_estimated_absorpt_T_min   0.719
_exptl_absorpt_coefficient_mu    3.208
_exptl_absorpt_correction_T_max  0.9904
_exptl_absorpt_correction_T_min  0.7072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;    
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1382 before and 0.1055 after correction. 
The Ratio of minimum to maximum transmission is 0.7141. 
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       blade
_exptl_crystal_F_000             1507
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0792
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6144
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.122
_diffrn_reflns_theta_min         3.317
_diffrn_ambient_temperature      100
_diffrn_detector                 'CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.69
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           1
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\mS HB'
_diffrn_source_voltage           50
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_full    0.952
_reflns_Friedel_fraction_max     0.852
_reflns_number_gt                5185
_reflns_number_total             6144
_reflns_special_details          
;
 _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_data_collection       
'BIS V6.2.9/2018-03-16 & APEX3 v2018.7-2 (Bruker-AXS, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker-AXS, 2016)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND 3 (Crystal Impact, 1999)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.113
_refine_ls_abs_structure_details 
;
 Flack x determined using 1819 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.163(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         6144
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0840
_refine_ls_restrained_S_all      1.064
_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)+(0.0956P)²+21.9971P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2207
_refine_ls_wR_factor_ref         0.2291
_refine_special_details          
;
 Refined as a 2-component twin with HKLF 5 file generated by PLATON TwinRotMat.
2-axis (   1   0  -2 ) [   0   0  -1 ], Angle () [] =  0.60 Deg, Freq =    14
        *************
(-0.998    0.000   -0.999)   (h1)   (h2)                   Nr Overlap =  1327
( 0.000   -1.000    0.000) * (k1) = (k2)                         BASF =  0.14
(-0.004    0.000    0.998)   (l1)   (l2)                        DEL-R =-0.007
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.846(7)
 0.154(7)
2. 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, All O(H) groups, All O(H,H) groups
3. Restrained distances
 C17-Cl3 \\sim C17-Cl4 \\sim C17-Cl2
 with sigma of 0.02
4. Others
 Sof(Cl2)=Sof(Cl3)=Sof(Cl4)=Sof(C17)=Sof(H17)=FVAR(1)
5.a Everything fixed:
 H17
5.b Free rotating group:
 O6(H6E,H6F,Cl2,Cl3,Cl4,C17)
5.c Ternary CH refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C11(H11), C13(H13), C7B(H7B), C9B(H9B), C10B(H10B),
 C11B(H11B), C13B(H13B)
5.d Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C14(H14A,H14B), C2B(H2C,
 H2D), C3B(H3C,H3D), C4B(H4D,H4C), C6B(H6C,H6D), C14B(H14C,H14D)
5.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C16B(H16D,H16E,H16F)
5.f Idealised tetrahedral OH refined as rotating group:
 O5(H5), O5B(H5B)
;
_atom_sites_solution_hydrogens   mixed
_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
Cl1 Cl 0.64620(7) 0.03495(16) 1.1229(4) 0.0355(6) Uani 1 1 d . . . . .
O1 O 0.62944(18) 0.1950(4) 1.2668(10) 0.0250(13) Uani 1 1 d . . . . .
O2 O 0.52813(18) 0.2980(5) 0.8327(10) 0.0291(15) Uani 1 1 d . . . . .
O3 O 0.68534(18) 0.3559(5) 1.1901(10) 0.0283(14) Uani 1 1 d . . . . .
O4 O 0.65079(17) 0.4844(4) 1.1323(10) 0.0253(14) Uani 1 1 d . . . . .
O5 O 0.59995(19) 0.4396(5) 0.7538(10) 0.0269(14) Uani 1 1 d . . . . .
H5 H 0.618688 0.474737 0.731386 0.040 Uiso 1 1 calc GR . . . .
C1 C 0.6013(2) 0.2698(6) 1.2313(13) 0.0226(18) Uani 1 1 d . . . . .
C2 C 0.5664(3) 0.2506(7) 1.3588(15) 0.031(2) Uani 1 1 d . . . . .
H2A H 0.575596 0.253247 1.504891 0.037 Uiso 1 1 calc R . . . .
H2B H 0.546167 0.299098 1.331329 0.037 Uiso 1 1 calc R . . . .
C3 C 0.5480(3) 0.1561(8) 1.3098(18) 0.038(2) Uani 1 1 d . . . . .
H3A H 0.531638 0.137984 1.419736 0.046 Uiso 1 1 calc R . . . .
H3B H 0.530664 0.160344 1.182135 0.046 Uiso 1 1 calc R . . . .
C4 C 0.5790(3) 0.0823(7) 1.2868(19) 0.040(3) Uani 1 1 d . . . . .
H4A H 0.591630 0.064620 1.421884 0.049 Uiso 1 1 calc R . . . .
H4B H 0.566707 0.026629 1.221837 0.049 Uiso 1 1 calc R . . . .
C5 C 0.6094(3) 0.1208(7) 1.1574(16) 0.030(2) Uani 1 1 d . . . . .
C6 C 0.5924(3) 0.1617(7) 0.9532(16) 0.032(2) Uani 1 1 d . . . . .
H6A H 0.609565 0.148542 0.843317 0.038 Uiso 1 1 calc R . . . .
H6B H 0.565578 0.138102 0.913645 0.038 Uiso 1 1 calc R . . . .
C7 C 0.5919(3) 0.2650(6) 1.0038(12) 0.0208(17) Uani 1 1 d . . . . .
H7 H 0.614533 0.293650 0.940641 0.025 Uiso 1 1 calc R . . . .
C8 C 0.5562(3) 0.3240(7) 0.9446(13) 0.0253(19) Uani 1 1 d . . . . .
C9 C 0.5591(2) 0.4203(6) 1.0287(12) 0.0212(18) Uani 1 1 d . . . . .
H9 H 0.532077 0.439054 1.060118 0.025 Uiso 1 1 calc R . . . .
C10 C 0.5876(3) 0.4396(6) 1.2246(13) 0.0188(17) Uani 1 1 d . . . . .
H10 H 0.571678 0.455281 1.339887 0.023 Uiso 1 1 calc R . . . .
C11 C 0.6178(2) 0.3656(6) 1.2938(13) 0.0198(17) Uani 1 1 d . . . . .
H11 H 0.622648 0.367976 1.445177 0.024 Uiso 1 1 calc R . . . .
C12 C 0.6543(3) 0.3974(7) 1.2019(13) 0.0233(19) Uani 1 1 d . . . . .
C13 C 0.6124(2) 0.5226(6) 1.1765(12) 0.0202(17) Uani 1 1 d . . . . .
H13 H 0.615201 0.567083 1.292569 0.024 Uiso 1 1 calc R . . . .
C14 C 0.5911(3) 0.5671(6) 0.9851(14) 0.0239(19) Uani 1 1 d . . . . .
H14A H 0.571018 0.611678 1.022923 0.029 Uiso 1 1 calc R . . . .
H14B H 0.610146 0.599867 0.905579 0.029 Uiso 1 1 calc R . . . .
C15 C 0.5723(2) 0.4889(7) 0.8647(13) 0.0229(18) Uani 1 1 d . . . . .
C16 C 0.5371(3) 0.5187(8) 0.7186(16) 0.037(2) Uani 1 1 d . . . . .
H16A H 0.546369 0.558761 0.613047 0.056 Uiso 1 1 calc GR . . . .
H16B H 0.518202 0.552470 0.794079 0.056 Uiso 1 1 calc GR . . . .
H16C H 0.524415 0.463959 0.655481 0.056 Uiso 1 1 calc GR . . . .
Cl1B Cl 0.55996(9) 0.7225(2) 1.4099(5) 0.0535(8) Uani 1 1 d . . . . .
O1B O 0.6287(2) 0.7010(5) 1.6090(11) 0.0354(16) Uani 1 1 d . . . . .
O2B O 0.7121(2) 0.8559(5) 1.2394(11) 0.0408(18) Uani 1 1 d . . . . .
O3B O 0.66496(18) 0.5146(5) 1.5897(10) 0.0307(15) Uani 1 1 d . . . . .
O4B O 0.72898(19) 0.5266(6) 1.5553(12) 0.0430(19) Uani 1 1 d . . . . .
O5B O 0.7372(2) 0.6411(5) 1.1759(11) 0.0330(15) Uani 1 1 d . . . . .
H5B H 0.745390 0.592064 1.126186 0.049 Uiso 1 1 calc GR . . . .
C1B C 0.6692(4) 0.7307(8) 1.6092(16) 0.042(3) Uani 1 1 d . . . . .
C2B C 0.6754(5) 0.8185(9) 1.7260(18) 0.064(4) Uani 1 1 d . . . . .
H2C H 0.702776 0.840103 1.716841 0.077 Uiso 1 1 calc R . . . .
H2D H 0.671880 0.806835 1.870866 0.077 Uiso 1 1 calc R . . . .
C3B C 0.6466(5) 0.8945(9) 1.6450(19) 0.065(4) Uani 1 1 d . . . . .
H3C H 0.656782 0.923887 1.524879 0.078 Uiso 1 1 calc R . . . .
H3D H 0.645114 0.942590 1.750619 0.078 Uiso 1 1 calc R . . . .
C4B C 0.6047(5) 0.8570(9) 1.585(2) 0.063(4) Uani 1 1 d . . . . .
H4D H 0.590598 0.847546 1.708160 0.075 Uiso 1 1 calc R . . . .
H4C H 0.589639 0.901892 1.496089 0.075 Uiso 1 1 calc R . . . .
C5B C 0.6081(3) 0.7679(8) 1.4762(17) 0.042(3) Uani 1 1 d . . . . .
C6B C 0.6326(3) 0.7773(7) 1.2972(15) 0.033(2) Uani 1 1 d . . . . .
H6C H 0.634684 0.842706 1.255709 0.039 Uiso 1 1 calc R . . . .
H6D H 0.621318 0.740760 1.179817 0.039 Uiso 1 1 calc R . . . .
C7B C 0.6725(3) 0.7396(7) 1.3782(13) 0.030(2) Uani 1 1 d . . . . .
H7B H 0.674398 0.675460 1.323693 0.036 Uiso 1 1 calc R . . . .
C8B C 0.7108(3) 0.7877(7) 1.3444(13) 0.032(2) Uani 1 1 d . . . . .
C9B C 0.7466(3) 0.7454(8) 1.4569(15) 0.040(3) Uani 1 1 d . . . . .
H9B H 0.765252 0.796492 1.498946 0.048 Uiso 1 1 calc R . . . .
C10B C 0.7409(3) 0.6845(10) 1.6518(15) 0.046(3) Uani 1 1 d . . . . .
H10B H 0.754245 0.715789 1.773855 0.055 Uiso 1 1 calc R . . . .
C11B C 0.6992(3) 0.6573(9) 1.6972(16) 0.042(3) Uani 1 1 d . . . . .
H11B H 0.698128 0.654701 1.847875 0.051 Uiso 1 1 calc R . . . .
C12B C 0.6950(3) 0.5610(8) 1.6141(16) 0.036(2) Uani 1 1 d . . . . .
C13B C 0.7614(3) 0.5924(10) 1.620(2) 0.055(4) Uani 1 1 d . . . . .
H13B H 0.776842 0.571150 1.747427 0.066 Uiso 1 1 calc R . . . .
C14B C 0.7873(3) 0.6067(10) 1.4504(19) 0.051(3) Uani 1 1 d . . . . .
H14C H 0.790258 0.548278 1.375413 0.061 Uiso 1 1 calc R . . . .
H14D H 0.813773 0.627854 1.504817 0.061 Uiso 1 1 calc R . . . .
C15B C 0.7675(3) 0.6800(8) 1.3096(15) 0.035(2) Uani 1 1 d . . . . .
C16B C 0.7962(3) 0.7313(9) 1.1897(15) 0.044(3) Uani 1 1 d . . . . .
H16D H 0.811278 0.687036 1.115182 0.066 Uiso 1 1 calc GR . . . .
H16E H 0.814317 0.767132 1.282601 0.066 Uiso 1 1 calc GR . . . .
H16F H 0.781825 0.773165 1.093282 0.066 Uiso 1 1 calc GR . . . .
O6 O 0.7478(2) 0.4630(5) 1.0479(12) 0.0412(18) Uani 1 1 d . . . . .
H6E H 0.768355 0.430329 1.025679 0.062 Uiso 1 1 d G . . . .
H6F H 0.729876 0.428067 1.131521 0.062 Uiso 1 1 d G . . . .
Cl2 Cl 0.5193(2) -0.0332(5) 0.7527(14) 0.100(5) Uani 0.379(9) 1 d DG . P A 1
Cl3 Cl 0.4852(3) -0.0647(9) 1.1220(19) 0.169(12) Uani 0.379(9) 1 d DG . P A 1
Cl4 Cl 0.5237(3) -0.2147(5) 0.939(2) 0.147(9) Uani 0.379(9) 1 d DG . P A 1
C17 C 0.4947(2) -0.1158(6) 0.8908(16) 0.13(3) Uiso 0.379(9) 1 d DG . P A 1
H17 H 0.471210 -0.131490 0.820340 0.155 Uiso 0.3788 1 d . . P A 1


_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
Cl1 C5 1.796(10) . ?
O1 C1 1.452(10) . ?
O1 C5 1.435(11) . ?
O2 C8 1.217(11) . ?
O3 C12 1.224(11) . ?
O4 C12 1.343(11) . ?
O4 C13 1.473(10) . ?
O5 H5 0.8400 . ?
O5 C15 1.434(10) . ?
C1 C2 1.542(12) . ?
C1 C7 1.512(12) . ?
C1 C11 1.541(12) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.528(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.521(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.505(15) . ?
C5 C6 1.540(13) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.533(13) . ?
C7 H7 1.0000 . ?
C7 C8 1.511(13) . ?
C8 C9 1.501(13) . ?
C9 H9 1.0000 . ?
C9 C10 1.576(12) . ?
C9 C15 1.564(12) . ?
C10 H10 1.0000 . ?
C10 C11 1.528(12) . ?
C10 C13 1.520(12) . ?
C11 H11 1.0000 . ?
C11 C12 1.504(12) . ?
C13 H13 1.0000 . ?
C13 C14 1.544(12) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.497(13) . ?
C15 C16 1.534(13) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
Cl1B C5B 1.788(13) . ?
O1B C1B 1.447(13) . ?
O1B C5B 1.448(13) . ?
O2B C8B 1.210(12) . ?
O3B C12B 1.223(12) . ?
O4B C12B 1.350(14) . ?
O4B C13B 1.495(14) . ?
O5B H5B 0.8400 . ?
O5B C15B 1.416(12) . ?
C1B C2B 1.494(16) . ?
C1B C7B 1.546(13) . ?
C1B C11B 1.553(18) . ?
C2B H2C 0.9900 . ?
C2B H2D 0.9900 . ?
C2B C3B 1.54(2) . ?
C3B H3C 0.9900 . ?
C3B H3D 0.9900 . ?
C3B C4B 1.55(2) . ?
C4B H4D 0.9900 . ?
C4B H4C 0.9900 . ?
C4B C5B 1.487(18) . ?
C5B C6B 1.513(15) . ?
C6B H6C 0.9900 . ?
C6B H6D 0.9900 . ?
C6B C7B 1.519(15) . ?
C7B H7B 1.0000 . ?
C7B C8B 1.514(13) . ?
C8B C9B 1.504(16) . ?
C9B H9B 1.0000 . ?
C9B C10B 1.586(14) . ?
C9B C15B 1.572(16) . ?
C10B H10B 1.0000 . ?
C10B C11B 1.531(15) . ?
C10B C13B 1.53(2) . ?
C11B H11B 1.0000 . ?
C11B C12B 1.502(17) . ?
C13B H13B 1.0000 . ?
C13B C14B 1.503(18) . ?
C14B H14C 0.9900 . ?
C14B H14D 0.9900 . ?
C14B C15B 1.531(16) . ?
C15B C16B 1.510(13) . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?
O6 H6E 0.8689 . ?
O6 H6F 0.9962 . ?
Cl2 Cl3 0.969(17) 2_657 ?
Cl2 C17 1.7602 . ?
Cl3 Cl4 2.227(5) 2_657 ?
Cl3 C17 1.7534 . ?
Cl4 C17 1.7546 . ?
C17 H17 0.9198 . ?

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
C5 O1 C1 101.4(6) . . ?
C12 O4 C13 109.9(7) . . ?
C15 O5 H5 109.5 . . ?
O1 C1 C2 107.9(7) . . ?
O1 C1 C7 102.0(7) . . ?
O1 C1 C11 114.1(7) . . ?
C7 C1 C2 115.3(8) . . ?
C7 C1 C11 110.5(7) . . ?
C11 C1 C2 107.3(7) . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 C1 111.5(8) . . ?
C3 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 C2 112.1(8) . . ?
C4 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C3 C4 H4A 110.0 . . ?
C3 C4 H4B 110.0 . . ?
H4A C4 H4B 108.4 . . ?
C5 C4 C3 108.3(8) . . ?
C5 C4 H4A 110.0 . . ?
C5 C4 H4B 110.0 . . ?
O1 C5 Cl1 105.9(6) . . ?
O1 C5 C4 108.2(9) . . ?
O1 C5 C6 106.3(8) . . ?
C4 C5 Cl1 109.7(7) . . ?
C4 C5 C6 114.6(8) . . ?
C6 C5 Cl1 111.7(7) . . ?
C5 C6 H6A 111.5 . . ?
C5 C6 H6B 111.5 . . ?
H6A C6 H6B 109.3 . . ?
C7 C6 C5 101.2(8) . . ?
C7 C6 H6A 111.5 . . ?
C7 C6 H6B 111.5 . . ?
C1 C7 C6 104.9(7) . . ?
C1 C7 H7 106.9 . . ?
C1 C7 C8 109.2(7) . . ?
C6 C7 H7 106.9 . . ?
C8 C7 C6 121.3(7) . . ?
C8 C7 H7 106.9 . . ?
O2 C8 C7 123.7(9) . . ?
O2 C8 C9 122.4(9) . . ?
C9 C8 C7 113.8(7) . . ?
C8 C9 H9 107.2 . . ?
C8 C9 C10 119.0(7) . . ?
C8 C9 C15 110.3(7) . . ?
C10 C9 H9 107.2 . . ?
C15 C9 H9 107.2 . . ?
C15 C9 C10 105.3(7) . . ?
C9 C10 H10 109.2 . . ?
C11 C10 C9 118.3(7) . . ?
C11 C10 H10 109.2 . . ?
C13 C10 C9 106.4(7) . . ?
C13 C10 H10 109.2 . . ?
C13 C10 C11 104.2(7) . . ?
C1 C11 H11 108.9 . . ?
C10 C11 C1 109.3(7) . . ?
C10 C11 H11 108.9 . . ?
C12 C11 C1 117.6(7) . . ?
C12 C11 C10 103.0(7) . . ?
C12 C11 H11 108.9 . . ?
O3 C12 O4 119.4(8) . . ?
O3 C12 C11 128.7(9) . . ?
O4 C12 C11 111.8(7) . . ?
O4 C13 C10 105.3(7) . . ?
O4 C13 H13 111.5 . . ?
O4 C13 C14 110.9(7) . . ?
C10 C13 H13 111.5 . . ?
C10 C13 C14 105.8(7) . . ?
C14 C13 H13 111.5 . . ?
C13 C14 H14A 110.6 . . ?
C13 C14 H14B 110.6 . . ?
H14A C14 H14B 108.7 . . ?
C15 C14 C13 105.7(7) . . ?
C15 C14 H14A 110.6 . . ?
C15 C14 H14B 110.6 . . ?
O5 C15 C9 106.2(7) . . ?
O5 C15 C14 112.1(7) . . ?
O5 C15 C16 109.3(7) . . ?
C14 C15 C9 104.4(7) . . ?
C14 C15 C16 113.5(8) . . ?
C16 C15 C9 111.1(7) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1B O1B C5B 102.4(8) . . ?
C12B O4B C13B 108.3(10) . . ?
C15B O5B H5B 109.5 . . ?
O1B C1B C2B 110.3(11) . . ?
O1B C1B C7B 100.1(8) . . ?
O1B C1B C11B 113.2(8) . . ?
C2B C1B C7B 114.9(9) . . ?
C2B C1B C11B 109.3(11) . . ?
C7B C1B C11B 109.0(9) . . ?
C1B C2B H2C 109.3 . . ?
C1B C2B H2D 109.3 . . ?
C1B C2B C3B 111.7(12) . . ?
H2C C2B H2D 107.9 . . ?
C3B C2B H2C 109.3 . . ?
C3B C2B H2D 109.3 . . ?
C2B C3B H3C 109.1 . . ?
C2B C3B H3D 109.1 . . ?
C2B C3B C4B 112.7(11) . . ?
H3C C3B H3D 107.8 . . ?
C4B C3B H3C 109.1 . . ?
C4B C3B H3D 109.1 . . ?
C3B C4B H4D 110.0 . . ?
C3B C4B H4C 110.0 . . ?
H4D C4B H4C 108.3 . . ?
C5B C4B C3B 108.7(11) . . ?
C5B C4B H4D 110.0 . . ?
C5B C4B H4C 110.0 . . ?
O1B C5B Cl1B 106.8(7) . . ?
O1B C5B C4B 110.0(10) . . ?
O1B C5B C6B 105.2(9) . . ?
C4B C5B Cl1B 109.2(10) . . ?
C4B C5B C6B 111.8(10) . . ?
C6B C5B Cl1B 113.5(8) . . ?
C5B C6B H6C 111.1 . . ?
C5B C6B H6D 111.1 . . ?
C5B C6B C7B 103.3(8) . . ?
H6C C6B H6D 109.1 . . ?
C7B C6B H6C 111.1 . . ?
C7B C6B H6D 111.1 . . ?
C1B C7B H7B 106.9 . . ?
C6B C7B C1B 103.8(8) . . ?
C6B C7B H7B 106.9 . . ?
C8B C7B C1B 108.8(8) . . ?
C8B C7B C6B 122.6(8) . . ?
C8B C7B H7B 106.9 . . ?
O2B C8B C7B 122.5(10) . . ?
O2B C8B C9B 123.2(9) . . ?
C9B C8B C7B 114.3(8) . . ?
C8B C9B H9B 107.8 . . ?
C8B C9B C10B 118.5(9) . . ?
C8B C9B C15B 109.3(8) . . ?
C10B C9B H9B 107.8 . . ?
C15B C9B H9B 107.8 . . ?
C15B C9B C10B 105.1(9) . . ?
C9B C10B H10B 108.9 . . ?
C11B C10B C9B 118.9(9) . . ?
C11B C10B H10B 108.9 . . ?
C13B C10B C9B 106.6(9) . . ?
C13B C10B H10B 108.9 . . ?
C13B C10B C11B 104.2(10) . . ?
C1B C11B H11B 108.6 . . ?
C10B C11B C1B 110.1(9) . . ?
C10B C11B H11B 108.6 . . ?
C12B C11B C1B 117.4(9) . . ?
C12B C11B C10B 103.2(10) . . ?
C12B C11B H11B 108.6 . . ?
O3B C12B O4B 119.2(10) . . ?
O3B C12B C11B 127.7(10) . . ?
O4B C12B C11B 113.0(9) . . ?
O4B C13B C10B 105.1(9) . . ?
O4B C13B H13B 111.6 . . ?
O4B C13B C14B 109.9(11) . . ?
C10B C13B H13B 111.6 . . ?
C14B C13B C10B 106.6(10) . . ?
C14B C13B H13B 111.6 . . ?
C13B C14B H14C 110.3 . . ?
C13B C14B H14D 110.3 . . ?
C13B C14B C15B 107.0(11) . . ?
H14C C14B H14D 108.6 . . ?
C15B C14B H14C 110.3 . . ?
C15B C14B H14D 110.3 . . ?
O5B C15B C9B 106.4(8) . . ?
O5B C15B C14B 111.3(9) . . ?
O5B C15B C16B 109.8(8) . . ?
C14B C15B C9B 104.0(9) . . ?
C16B C15B C9B 112.2(9) . . ?
C16B C15B C14B 112.8(9) . . ?
C15B C16B H16D 109.5 . . ?
C15B C16B H16E 109.5 . . ?
C15B C16B H16F 109.5 . . ?
H16D C16B H16E 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
H6E O6 H6F 111.1 . . ?
Cl3 Cl2 C17 28.3(8) 2_657 . ?
Cl2 Cl3 Cl4 125.8(10) 2_657 2_657 ?
Cl2 Cl3 C17 176.6(7) 2_657 . ?
C17 Cl3 Cl4 57.4(6) . 2_657 ?
Cl2 C17 Cl4 170.4(6) . 2_657 ?
Cl2 C17 H17 109.8 . . ?
Cl3 C17 Cl2 107.2 . . ?
Cl3 C17 Cl2 26.9(11) 2_657 . ?
Cl3 C17 Cl3 86.6(10) 2_657 . ?
Cl3 C17 Cl4 146.3(17) 2_657 2_657 ?
Cl3 C17 Cl4 103.7(6) 2_657 . ?
Cl3 C17 Cl4 73.5(5) . 2_657 ?
Cl3 C17 Cl4 109.3 . . ?
Cl3 C17 H17 134.5 2_657 . ?
Cl3 C17 H17 109.0 . . ?
Cl4 C17 Cl2 111.4 . . ?
Cl4 C17 Cl4 60.1(6) . 2_657 ?
Cl4 C17 H17 78.5 2_657 . ?
Cl4 C17 H17 110.1 . . ?

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
_geom_hbond_publ_flag
O5 H5 O3B 0.84 1.99 2.772(9) 154.9 1_554 yes
O5B H5B O6 0.84 1.94 2.749(10) 160.2 . yes
O6 H6E O2B 0.87 2.21 2.886(10) 134.6 4_647 yes
O6 H6F O3 1.00 1.91 2.858(9) 157.8 . yes

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
Cl1 C5 C6 C7 -135.7(7) . . . . ?
O1 C1 C2 C3 -56.0(10) . . . . ?
O1 C1 C7 C6 36.0(9) . . . . ?
O1 C1 C7 C8 167.4(7) . . . . ?
O1 C1 C11 C10 172.7(7) . . . . ?
O1 C1 C11 C12 55.9(10) . . . . ?
O1 C5 C6 C7 -20.7(10) . . . . ?
O2 C8 C9 C10 159.3(8) . . . . ?
O2 C8 C9 C15 -78.9(10) . . . . ?
O4 C13 C14 C15 81.2(8) . . . . ?
C1 O1 C5 Cl1 162.9(6) . . . . ?
C1 O1 C5 C4 -79.5(8) . . . . ?
C1 O1 C5 C6 44.0(9) . . . . ?
C1 C2 C3 C4 41.8(12) . . . . ?
C1 C7 C8 O2 -131.9(9) . . . . ?
C1 C7 C8 C9 50.8(10) . . . . ?
C1 C11 C12 O3 -49.2(12) . . . . ?
C1 C11 C12 O4 133.0(8) . . . . ?
C2 C1 C7 C6 -80.7(10) . . . . ?
C2 C1 C7 C8 50.8(10) . . . . ?
C2 C1 C11 C10 -67.8(8) . . . . ?
C2 C1 C11 C12 175.4(8) . . . . ?
C2 C3 C4 C5 -45.3(12) . . . . ?
C3 C4 C5 Cl1 -179.1(8) . . . . ?
C3 C4 C5 O1 65.8(11) . . . . ?
C3 C4 C5 C6 -52.5(12) . . . . ?
C4 C5 C6 C7 98.7(10) . . . . ?
C5 O1 C1 C2 72.7(8) . . . . ?
C5 O1 C1 C7 -49.1(8) . . . . ?
C5 O1 C1 C11 -168.2(7) . . . . ?
C5 C6 C7 C1 -9.4(9) . . . . ?
C5 C6 C7 C8 -133.5(8) . . . . ?
C6 C7 C8 O2 -9.8(14) . . . . ?
C6 C7 C8 C9 172.9(8) . . . . ?
C7 C1 C2 C3 57.1(11) . . . . ?
C7 C1 C11 C10 58.6(9) . . . . ?
C7 C1 C11 C12 -58.2(10) . . . . ?
C7 C8 C9 C10 -23.3(11) . . . . ?
C7 C8 C9 C15 98.5(8) . . . . ?
C8 C9 C10 C11 13.5(11) . . . . ?
C8 C9 C10 C13 130.2(8) . . . . ?
C8 C9 C15 O5 -36.7(9) . . . . ?
C8 C9 C15 C14 -155.2(7) . . . . ?
C8 C9 C15 C16 82.1(9) . . . . ?
C9 C10 C11 C1 -29.8(10) . . . . ?
C9 C10 C11 C12 96.0(8) . . . . ?
C9 C10 C13 O4 -102.0(7) . . . . ?
C9 C10 C13 C14 15.5(8) . . . . ?
C10 C9 C15 O5 93.0(7) . . . . ?
C10 C9 C15 C14 -25.6(9) . . . . ?
C10 C9 C15 C16 -148.3(8) . . . . ?
C10 C11 C12 O3 -169.4(8) . . . . ?
C10 C11 C12 O4 12.8(9) . . . . ?
C10 C13 C14 C15 -32.4(9) . . . . ?
C11 C1 C2 C3 -179.4(7) . . . . ?
C11 C1 C7 C6 157.5(7) . . . . ?
C11 C1 C7 C8 -71.0(9) . . . . ?
C11 C10 C13 O4 23.8(8) . . . . ?
C11 C10 C13 C14 141.3(7) . . . . ?
C12 O4 C13 C10 -16.8(8) . . . . ?
C12 O4 C13 C14 -130.7(7) . . . . ?
C13 O4 C12 O3 -175.7(7) . . . . ?
C13 O4 C12 C11 2.4(9) . . . . ?
C13 C10 C11 C1 -147.6(7) . . . . ?
C13 C10 C11 C12 -21.9(8) . . . . ?
C13 C14 C15 O5 -78.7(9) . . . . ?
C13 C14 C15 C9 35.7(9) . . . . ?
C13 C14 C15 C16 156.8(7) . . . . ?
C15 C9 C10 C11 -110.8(8) . . . . ?
C15 C9 C10 C13 5.9(8) . . . . ?
Cl1B C5B C6B C7B -135.5(7) . . . . ?
O1B C1B C2B C3B -55.2(13) . . . . ?
O1B C1B C7B C6B 37.4(10) . . . . ?
O1B C1B C7B C8B 169.4(8) . . . . ?
O1B C1B C11B C10B 168.1(9) . . . . ?
O1B C1B C11B C12B 50.5(12) . . . . ?
O1B C5B C6B C7B -19.1(10) . . . . ?
O2B C8B C9B C10B 155.9(10) . . . . ?
O2B C8B C9B C15B -83.8(11) . . . . ?
O4B C13B C14B C15B 83.0(13) . . . . ?
C1B O1B C5B Cl1B 165.3(7) . . . . ?
C1B O1B C5B C4B -76.3(11) . . . . ?
C1B O1B C5B C6B 44.3(10) . . . . ?
C1B C2B C3B C4B 39.5(14) . . . . ?
C1B C7B C8B O2B -126.1(11) . . . . ?
C1B C7B C8B C9B 52.1(11) . . . . ?
C1B C11B C12B O3B -48.0(15) . . . . ?
C1B C11B C12B O4B 129.5(9) . . . . ?
C2B C1B C7B C6B -80.8(13) . . . . ?
C2B C1B C7B C8B 51.3(15) . . . . ?
C2B C1B C11B C10B -68.5(12) . . . . ?
C2B C1B C11B C12B 173.9(9) . . . . ?
C2B C3B C4B C5B -42.0(14) . . . . ?
C3B C4B C5B Cl1B 179.0(9) . . . . ?
C3B C4B C5B O1B 62.0(12) . . . . ?
C3B C4B C5B C6B -54.5(14) . . . . ?
C4B C5B C6B C7B 100.3(11) . . . . ?
C5B O1B C1B C2B 71.4(11) . . . . ?
C5B O1B C1B C7B -50.0(10) . . . . ?
C5B O1B C1B C11B -165.8(9) . . . . ?
C5B C6B C7B C1B -11.2(10) . . . . ?
C5B C6B C7B C8B -134.6(9) . . . . ?
C6B C7B C8B O2B -5.0(14) . . . . ?
C6B C7B C8B C9B 173.2(9) . . . . ?
C7B C1B C2B C3B 57.0(15) . . . . ?
C7B C1B C11B C10B 57.7(11) . . . . ?
C7B C1B C11B C12B -59.9(11) . . . . ?
C7B C8B C9B C10B -22.3(13) . . . . ?
C7B C8B C9B C15B 98.0(9) . . . . ?
C8B C9B C10B C11B 10.3(16) . . . . ?
C8B C9B C10B C13B 127.5(10) . . . . ?
C8B C9B C15B O5B -33.4(10) . . . . ?
C8B C9B C15B C14B -151.0(8) . . . . ?
C8B C9B C15B C16B 86.7(10) . . . . ?
C9B C10B C11B C1B -27.7(14) . . . . ?
C9B C10B C11B C12B 98.3(12) . . . . ?
C9B C10B C13B O4B -101.6(9) . . . . ?
C9B C10B C13B C14B 15.1(11) . . . . ?
C10B C9B C15B O5B 94.9(9) . . . . ?
C10B C9B C15B C14B -22.7(10) . . . . ?
C10B C9B C15B C16B -145.0(9) . . . . ?
C10B C11B C12B O3B -169.2(10) . . . . ?
C10B C11B C12B O4B 8.2(11) . . . . ?
C10B C13B C14B C15B -30.4(13) . . . . ?
C11B C1B C2B C3B 179.8(10) . . . . ?
C11B C1B C7B C6B 156.3(8) . . . . ?
C11B C1B C7B C8B -71.6(10) . . . . ?
C11B C10B C13B O4B 25.0(11) . . . . ?
C11B C10B C13B C14B 141.7(9) . . . . ?
C12B O4B C13B C10B -20.7(11) . . . . ?
C12B O4B C13B C14B -135.1(11) . . . . ?
C13B O4B C12B O3B -174.5(9) . . . . ?
C13B O4B C12B C11B 7.8(11) . . . . ?
C13B C10B C11B C1B -146.2(9) . . . . ?
C13B C10B C11B C12B -20.1(11) . . . . ?
C13B C14B C15B O5B -81.1(12) . . . . ?
C13B C14B C15B C9B 33.1(12) . . . . ?
C13B C14B C15B C16B 154.9(10) . . . . ?
C15B C9B C10B C11B -112.2(12) . . . . ?
C15B C9B C10B C13B 5.0(10) . . . . ?
Cl3 Cl2 C17 Cl3 41.5(13) 2_657 . . . ?
Cl3 Cl2 C17 Cl4 -78.0(13) 2_657 . . . ?
Cl4 Cl3 C17 Cl2 -170.0(7) 2_657 . . . ?
Cl4 Cl3 C17 Cl3 -152.5(14) 2_657 . . 2_657 ?
Cl4 Cl3 C17 Cl4 -49.2(7) 2_657 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.846(7)
2 0.154(7)

####################################################################### 
# 
# 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_V19015
_database_code_depnum_ccdc_archive 'CCDC 2239963'
loop_
_audit_author_name
_audit_author_address
'Michel Takase'
;California Institute of Technology
United States of America
;
_audit_update_record             
;
2023-02-05 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H30 O4 Si'
_chemical_formula_weight         410.57

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'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   6.7649(5)
_cell_length_b                   10.9273(9)
_cell_length_c                   14.4629(14)
_cell_angle_alpha                90
_cell_angle_beta                 103.394(5)
_cell_angle_gamma                90
_cell_volume                     1040.05(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9924
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      74.56

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.224
_shelx_estimated_absorpt_T_min   0.792
_shelx_estimated_absorpt_T_max   0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5626
_exptl_absorpt_correction_T_max  0.7504
_exptl_absorpt_process_details   'SADABS-2016/2 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS HB micro-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.69
_diffrn_reflns_number            17179
_diffrn_reflns_av_unetI/netI     0.0649
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.141
_diffrn_reflns_theta_max         74.630
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4172
_reflns_number_gt                4078
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.896
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.997

_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       'APEX3 v2017.3-0 (Bruker-AXS, 2017)'
_computing_cell_refinement       'SAINT v8.38A (Bruker-AXS, 2013)'
_computing_data_reduction        'SAINT v8.38A (Bruker-AXS, 2013)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1772P)²+0.7893P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1784 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 

 Bayesian Statistics
 Student_T Nu       11
 Select Pairs     1932
 Theta_Min ..     5.12
 Theta_Max ..    74.63
 P2(true)....      n/a
 P3(true)....    0.777
 P3(rac-twin)    0.223
 P3(false) ..  0.2E-37
 G ..........   0.5135
 G (su) .....   0.1047
 Hooft y ....  0.24(5)

;
_refine_ls_abs_structure_Flack   0.03(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4172
_refine_ls_number_parameters     269
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0880
_refine_ls_wR_factor_ref         0.2312
_refine_ls_wR_factor_gt          0.2288
_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
Si1 Si 0.5500(3) 0.3644(2) 0.37331(16) 0.0263(5) Uani 1 1 d . . . . .
C1 C 0.5454(13) 0.4028(8) 0.5009(6) 0.0277(17) Uani 1 1 d . . . . .
C2 C 0.3622(15) 0.4276(9) 0.5275(7) 0.0335(19) Uani 1 1 d . . . . .
H2 H 0.238043 0.424225 0.480624 0.040 Uiso 1 1 calc R U . . .
C3 C 0.3582(16) 0.4570(10) 0.6208(8) 0.038(2) Uani 1 1 d . . . . .
H3 H 0.232952 0.475069 0.636861 0.045 Uiso 1 1 calc R U . . .
C4 C 0.5409(17) 0.4598(10) 0.6909(8) 0.037(2) Uani 1 1 d . . . . .
H4 H 0.539698 0.479863 0.754702 0.044 Uiso 1 1 calc R U . . .
C5 C 0.7217(15) 0.4334(10) 0.6668(7) 0.035(2) Uani 1 1 d . . . . .
H5 H 0.844897 0.433324 0.714391 0.042 Uiso 1 1 calc R U . . .
C6 C 0.7249(16) 0.4064(9) 0.5719(7) 0.0343(19) Uani 1 1 d . . . . .
H6 H 0.851008 0.390343 0.555939 0.041 Uiso 1 1 calc R U . . .
C7 C 0.3130(15) 0.2738(10) 0.3256(7) 0.0344(19) Uani 1 1 d . . . . .
H7A H 0.194645 0.327985 0.316141 0.052 Uiso 1 1 calc R U . . .
H7B H 0.300402 0.209205 0.370891 0.052 Uiso 1 1 calc R U . . .
H7C H 0.320127 0.236707 0.264717 0.052 Uiso 1 1 calc R U . . .
C8 C 0.7879(13) 0.2754(9) 0.3754(8) 0.0332(18) Uani 1 1 d . . . . .
H8A H 0.804465 0.211860 0.424437 0.050 Uiso 1 1 calc R U . . .
H8B H 0.905064 0.330711 0.389676 0.050 Uiso 1 1 calc R U . . .
H8C H 0.778491 0.237147 0.313277 0.050 Uiso 1 1 calc R U . . .
C11 C 0.5539(13) 0.5208(8) 0.3156(6) 0.0265(16) Uani 1 1 d . . . . .
C12 C 0.3363(14) 0.5841(9) 0.3012(7) 0.0315(18) Uani 1 1 d . . . . .
H12A H 0.241707 0.539833 0.332371 0.038 Uiso 1 1 calc R U . . .
H12B H 0.342564 0.672082 0.317979 0.038 Uiso 1 1 calc R U . . .
C13 C 0.2992(13) 0.5596(8) 0.1937(6) 0.0262(17) Uani 1 1 d . . . . .
H13 H 0.235371 0.477246 0.178878 0.031 Uiso 1 1 calc R U . . .
C14 C 0.2128(13) 0.6460(8) 0.1150(6) 0.0262(16) Uani 1 1 d . . . . .
O1 O 0.1187(12) 0.7376(6) 0.1210(5) 0.0344(15) Uani 1 1 d . . . . .
C15 C 0.2743(13) 0.6116(8) 0.0223(6) 0.0269(17) Uani 1 1 d . . . . .
H15 H 0.281675 0.690008 -0.012422 0.032 Uiso 1 1 calc R U . . .
C16 C 0.1075(14) 0.5330(8) -0.0431(6) 0.0277(16) Uani 1 1 d . . . . .
C26 C -0.0690(15) 0.6100(9) -0.0971(7) 0.034(2) Uani 1 1 d . . . . .
H26A H -0.169119 0.556929 -0.138073 0.051 Uiso 1 1 calc R U . . .
H26B H -0.018777 0.670444 -0.136215 0.051 Uiso 1 1 calc R U . . .
H26C H -0.132942 0.652356 -0.051846 0.051 Uiso 1 1 calc R U . . .
O2 O 0.0321(10) 0.4436(6) 0.0135(5) 0.0306(13) Uani 1 1 d D . . . .
H2A H -0.01(2) 0.386(9) -0.023(8) 0.046 Uiso 1 1 d D U . . .
C17 C 0.2279(15) 0.4700(8) -0.1074(6) 0.0284(17) Uani 1 1 d . . . . .
H17A H 0.157304 0.394788 -0.135662 0.034 Uiso 1 1 calc R U . . .
H17B H 0.243284 0.525474 -0.159391 0.034 Uiso 1 1 calc R U . . .
C18 C 0.4326(15) 0.4391(8) -0.0447(6) 0.0290(18) Uani 1 1 d . . . . .
H18 H 0.538466 0.431749 -0.082508 0.035 Uiso 1 1 calc R U . . .
C19 C 0.4824(13) 0.5439(8) 0.0283(6) 0.0255(16) Uani 1 1 d . . . . .
H19 H 0.581428 0.601426 0.009630 0.031 Uiso 1 1 calc R U . . .
C20 C 0.5848(13) 0.4788(8) 0.1237(6) 0.0268(17) Uani 1 1 d . . . . .
H20 H 0.735535 0.480621 0.131581 0.032 Uiso 1 1 calc R U . . .
C21 C 0.5101(13) 0.3456(8) 0.1047(6) 0.0268(17) Uani 1 1 d . . . . .
O3 O 0.4251(10) 0.3301(6) 0.0116(5) 0.0295(13) Uani 1 1 d . . . . .
O4 O 0.5290(12) 0.2622(6) 0.1593(5) 0.0345(15) Uani 1 1 d . . . . .
C22 C 0.5312(13) 0.5490(8) 0.2053(6) 0.0274(17) Uani 1 1 d . . . . .
C23 C 0.6384(15) 0.6755(8) 0.2115(7) 0.0302(19) Uani 1 1 d . . . . .
H23A H 0.683199 0.693199 0.152388 0.036 Uiso 1 1 calc R U . . .
H23B H 0.546163 0.741635 0.222238 0.036 Uiso 1 1 calc R U . . .
C24 C 0.8208(15) 0.6643(10) 0.2960(8) 0.039(2) Uani 1 1 d . . . . .
H24A H 0.874564 0.745869 0.318863 0.047 Uiso 1 1 calc R U . . .
H24B H 0.930837 0.615593 0.279232 0.047 Uiso 1 1 calc R U . . .
C25 C 0.7315(15) 0.5980(9) 0.3715(7) 0.0335(19) Uani 1 1 d . . . . .
H25A H 0.835276 0.544982 0.411913 0.040 Uiso 1 1 calc R U . . .
H25B H 0.682948 0.657920 0.412545 0.040 Uiso 1 1 calc R U . . .


_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
Si1 C8 1.874(9) . ?
Si1 C7 1.875(10) . ?
Si1 C1 1.900(9) . ?
Si1 C11 1.905(9) . ?
C1 C6 1.397(13) . ?
C1 C2 1.406(13) . ?
C2 C3 1.393(14) . ?
C2 H2 0.9500 . ?
C3 C4 1.406(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.378(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.409(14) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C11 C25 1.535(12) . ?
C11 C12 1.596(12) . ?
C11 C22 1.598(12) . ?
C12 C13 1.541(13) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.489(12) . ?
C13 C22 1.544(12) . ?
C13 H13 1.0000 . ?
C14 O1 1.201(12) . ?
C14 C15 1.541(12) . ?
C15 C16 1.552(12) . ?
C15 C19 1.574(12) . ?
C15 H15 1.0000 . ?
C16 O2 1.441(11) . ?
C16 C26 1.521(13) . ?
C16 C17 1.534(12) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
O2 H2A 0.83(3) . ?
C17 C18 1.508(13) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 O3 1.450(11) . ?
C18 C19 1.541(12) . ?
C18 H18 1.0000 . ?
C19 C20 1.565(12) . ?
C19 H19 1.0000 . ?
C20 C22 1.520(12) . ?
C20 C21 1.544(12) . ?
C20 H20 1.0000 . ?
C21 O4 1.193(11) . ?
C21 O3 1.347(11) . ?
C22 C23 1.554(13) . ?
C23 C24 1.527(13) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.545(14) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?

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
C8 Si1 C7 112.9(5) . . ?
C8 Si1 C1 107.8(4) . . ?
C7 Si1 C1 105.7(4) . . ?
C8 Si1 C11 111.9(4) . . ?
C7 Si1 C11 114.2(4) . . ?
C1 Si1 C11 103.4(4) . . ?
C6 C1 C2 117.7(9) . . ?
C6 C1 Si1 120.9(7) . . ?
C2 C1 Si1 121.4(7) . . ?
C3 C2 C1 121.7(9) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 119.5(10) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 119.7(10) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.4(9) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 121.0(9) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
Si1 C7 H7A 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
Si1 C8 H8A 109.5 . . ?
Si1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Si1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C25 C11 C12 114.6(7) . . ?
C25 C11 C22 107.6(7) . . ?
C12 C11 C22 85.0(6) . . ?
C25 C11 Si1 110.5(6) . . ?
C12 C11 Si1 109.9(6) . . ?
C22 C11 Si1 127.1(6) . . ?
C13 C12 C11 89.2(7) . . ?
C13 C12 H12A 113.8 . . ?
C11 C12 H12A 113.8 . . ?
C13 C12 H12B 113.8 . . ?
C11 C12 H12B 113.8 . . ?
H12A C12 H12B 111.0 . . ?
C14 C13 C12 127.2(8) . . ?
C14 C13 C22 109.9(7) . . ?
C12 C13 C22 88.8(7) . . ?
C14 C13 H13 109.5 . . ?
C12 C13 H13 109.5 . . ?
C22 C13 H13 109.5 . . ?
O1 C14 C13 126.4(8) . . ?
O1 C14 C15 121.4(8) . . ?
C13 C14 C15 111.9(7) . . ?
C14 C15 C16 111.1(7) . . ?
C14 C15 C19 119.0(7) . . ?
C16 C15 C19 106.8(7) . . ?
C14 C15 H15 106.4 . . ?
C16 C15 H15 106.4 . . ?
C19 C15 H15 106.4 . . ?
O2 C16 C26 109.1(8) . . ?
O2 C16 C17 110.3(7) . . ?
C26 C16 C17 113.6(7) . . ?
O2 C16 C15 109.4(7) . . ?
C26 C16 C15 112.3(7) . . ?
C17 C16 C15 101.8(7) . . ?
C16 C26 H26A 109.5 . . ?
C16 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C16 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C16 O2 H2A 106(10) . . ?
C18 C17 C16 106.2(7) . . ?
C18 C17 H17A 110.5 . . ?
C16 C17 H17A 110.5 . . ?
C18 C17 H17B 110.5 . . ?
C16 C17 H17B 110.5 . . ?
H17A C17 H17B 108.7 . . ?
O3 C18 C17 112.0(7) . . ?
O3 C18 C19 104.9(7) . . ?
C17 C18 C19 105.7(7) . . ?
O3 C18 H18 111.3 . . ?
C17 C18 H18 111.3 . . ?
C19 C18 H18 111.3 . . ?
C18 C19 C20 104.4(7) . . ?
C18 C19 C15 105.1(7) . . ?
C20 C19 C15 118.0(7) . . ?
C18 C19 H19 109.7 . . ?
C20 C19 H19 109.7 . . ?
C15 C19 H19 109.7 . . ?
C22 C20 C21 119.2(7) . . ?
C22 C20 C19 108.6(6) . . ?
C21 C20 C19 102.2(7) . . ?
C22 C20 H20 108.8 . . ?
C21 C20 H20 108.8 . . ?
C19 C20 H20 108.8 . . ?
O4 C21 O3 121.4(8) . . ?
O4 C21 C20 128.5(8) . . ?
O3 C21 C20 110.1(7) . . ?
C21 O3 C18 113.3(7) . . ?
C20 C22 C13 111.9(7) . . ?
C20 C22 C23 107.6(7) . . ?
C13 C22 C23 112.9(8) . . ?
C20 C22 C11 133.8(7) . . ?
C13 C22 C11 89.0(6) . . ?
C23 C22 C11 100.2(7) . . ?
C24 C23 C22 104.8(8) . . ?
C24 C23 H23A 110.8 . . ?
C22 C23 H23A 110.8 . . ?
C24 C23 H23B 110.8 . . ?
C22 C23 H23B 110.8 . . ?
H23A C23 H23B 108.9 . . ?
C23 C24 C25 103.1(8) . . ?
C23 C24 H24A 111.1 . . ?
C25 C24 H24A 111.1 . . ?
C23 C24 H24B 111.1 . . ?
C25 C24 H24B 111.1 . . ?
H24A C24 H24B 109.1 . . ?
C11 C25 C24 105.8(8) . . ?
C11 C25 H25A 110.6 . . ?
C24 C25 H25A 110.6 . . ?
C11 C25 H25B 110.6 . . ?
C24 C25 H25B 110.6 . . ?
H25A C25 H25B 108.7 . . ?

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
C8 Si1 C1 C6 23.2(9) . . . . ?
C7 Si1 C1 C6 144.2(8) . . . . ?
C11 Si1 C1 C6 -95.5(8) . . . . ?
C8 Si1 C1 C2 -156.3(8) . . . . ?
C7 Si1 C1 C2 -35.2(9) . . . . ?
C11 Si1 C1 C2 85.1(8) . . . . ?
C6 C1 C2 C3 1.2(15) . . . . ?
Si1 C1 C2 C3 -179.4(8) . . . . ?
C1 C2 C3 C4 -1.3(15) . . . . ?
C2 C3 C4 C5 -0.1(16) . . . . ?
C3 C4 C5 C6 1.5(16) . . . . ?
C2 C1 C6 C5 0.3(15) . . . . ?
Si1 C1 C6 C5 -179.2(8) . . . . ?
C4 C5 C6 C1 -1.6(16) . . . . ?
C25 C11 C12 C13 127.8(8) . . . . ?
C22 C11 C12 C13 20.7(6) . . . . ?
Si1 C11 C12 C13 -107.0(6) . . . . ?
C11 C12 C13 C14 -135.6(8) . . . . ?
C11 C12 C13 C22 -21.4(7) . . . . ?
C12 C13 C14 O1 -17.2(15) . . . . ?
C22 C13 C14 O1 -121.5(10) . . . . ?
C12 C13 C14 C15 157.4(8) . . . . ?
C22 C13 C14 C15 53.1(10) . . . . ?
O1 C14 C15 C16 -89.6(11) . . . . ?
C13 C14 C15 C16 95.4(8) . . . . ?
O1 C14 C15 C19 145.8(9) . . . . ?
C13 C14 C15 C19 -29.2(11) . . . . ?
C14 C15 C16 O2 -42.2(10) . . . . ?
C19 C15 C16 O2 89.0(8) . . . . ?
C14 C15 C16 C26 79.1(9) . . . . ?
C19 C15 C16 C26 -149.6(8) . . . . ?
C14 C15 C16 C17 -159.0(7) . . . . ?
C19 C15 C16 C17 -27.8(8) . . . . ?
O2 C16 C17 C18 -77.6(9) . . . . ?
C26 C16 C17 C18 159.5(7) . . . . ?
C15 C16 C17 C18 38.5(8) . . . . ?
C16 C17 C18 O3 79.1(8) . . . . ?
C16 C17 C18 C19 -34.6(9) . . . . ?
O3 C18 C19 C20 22.3(8) . . . . ?
C17 C18 C19 C20 140.8(7) . . . . ?
O3 C18 C19 C15 -102.6(7) . . . . ?
C17 C18 C19 C15 16.0(9) . . . . ?
C14 C15 C19 C18 134.4(8) . . . . ?
C16 C15 C19 C18 7.8(9) . . . . ?
C14 C15 C19 C20 18.7(11) . . . . ?
C16 C15 C19 C20 -107.9(8) . . . . ?
C18 C19 C20 C22 -147.5(7) . . . . ?
C15 C19 C20 C22 -31.4(10) . . . . ?
C18 C19 C20 C21 -20.7(8) . . . . ?
C15 C19 C20 C21 95.4(8) . . . . ?
C22 C20 C21 O4 -51.9(12) . . . . ?
C19 C20 C21 O4 -171.5(9) . . . . ?
C22 C20 C21 O3 132.0(8) . . . . ?
C19 C20 C21 O3 12.4(8) . . . . ?
O4 C21 O3 C18 -174.6(8) . . . . ?
C20 C21 O3 C18 1.9(9) . . . . ?
C17 C18 O3 C21 -129.8(7) . . . . ?
C19 C18 O3 C21 -15.7(9) . . . . ?
C21 C20 C22 C13 -59.4(10) . . . . ?
C19 C20 C22 C13 57.0(9) . . . . ?
C21 C20 C22 C23 176.1(7) . . . . ?
C19 C20 C22 C23 -67.6(8) . . . . ?
C21 C20 C22 C11 51.8(13) . . . . ?
C19 C20 C22 C11 168.1(9) . . . . ?
C14 C13 C22 C20 -71.5(10) . . . . ?
C12 C13 C22 C20 159.0(7) . . . . ?
C14 C13 C22 C23 50.1(10) . . . . ?
C12 C13 C22 C23 -79.4(8) . . . . ?
C14 C13 C22 C11 150.8(7) . . . . ?
C12 C13 C22 C11 21.3(7) . . . . ?
C25 C11 C22 C20 105.0(10) . . . . ?
C12 C11 C22 C20 -140.7(10) . . . . ?
Si1 C11 C22 C20 -29.5(13) . . . . ?
C25 C11 C22 C13 -134.9(7) . . . . ?
C12 C11 C22 C13 -20.6(7) . . . . ?
Si1 C11 C22 C13 90.6(8) . . . . ?
C25 C11 C22 C23 -21.8(8) . . . . ?
C12 C11 C22 C23 92.4(7) . . . . ?
Si1 C11 C22 C23 -156.3(7) . . . . ?
C20 C22 C23 C24 -103.1(8) . . . . ?
C13 C22 C23 C24 132.9(8) . . . . ?
C11 C22 C23 C24 39.6(9) . . . . ?
C22 C23 C24 C25 -43.1(10) . . . . ?
C12 C11 C25 C24 -96.0(9) . . . . ?
C22 C11 C25 C24 -3.4(10) . . . . ?
Si1 C11 C25 C24 139.2(7) . . . . ?
C23 C24 C25 C11 28.0(10) . . . . ?

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
_geom_hbond_publ_flag
C13 H13 O2 1.00 2.49 3.079(11) 116.9 . yes
C15 H15 O3 1.00 2.50 3.246(11) 130.8 2_655 yes
O2 H2A O1 0.83(3) 2.16(3) 2.996(10) 178(15) 2_545 yes
C17 H17A O1 0.99 2.58 3.430(11) 143.8 2_545 yes
C19 H19 O3 1.00 2.52 3.267(11) 131.5 2_655 yes

_refine_diff_density_max         0.686
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.089

####################################################################### 
# 
# 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_V20005
_audit_block_doi                 10.5517/ccdc.csd.cc24qp0l
_database_code_depnum_ccdc_archive 'CCDC 1987999'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/jacs.0c02513 2020
loop_
_audit_author_name
_audit_author_address
'Michael Takase'
;California Institute of Technology
United States of America
;
_audit_update_record             
;
2020-03-03 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H32 O9'
_chemical_formula_weight         404.44

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

_cell_length_a                   9.0245(13)
_cell_length_b                   13.383(2)
_cell_length_c                   16.329(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1972.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9811
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      74.36

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.906
_shelx_estimated_absorpt_T_min   0.613
_shelx_estimated_absorpt_T_max   0.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5503
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   'SADABS-2016/2 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS HB micro-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.69
_diffrn_reflns_number            20468
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.271
_diffrn_reflns_theta_max         74.810
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4017
_reflns_number_gt                3996
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_fraction_full    0.999

_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       'APEX3 v2019.1-0 (Bruker Nano, 2019)'
_computing_cell_refinement       'SAINT v8.40A (Bruker-AXS, 2013)'
_computing_data_reduction        'SAINT v8.40A (Bruker-AXS, 2013)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0537P)²+0.3996P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1695 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.06(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4017
_refine_ls_number_parameters     282
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0875
_refine_ls_wR_factor_gt          0.0874
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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 0.74876(16) 0.50700(10) 0.87863(8) 0.0199(3) Uani 1 1 d . . . . .
C1 C 0.6251(2) 0.51775(13) 0.83404(11) 0.0169(4) Uani 1 1 d . . . . .
O2 O 0.53313(16) 0.57937(10) 0.85278(9) 0.0229(3) Uani 1 1 d . . . . .
C2 C 0.62436(19) 0.44541(13) 0.76228(10) 0.0136(3) Uani 1 1 d . . . . .
H2 H 0.663034 0.480078 0.712422 0.016 Uiso 1 1 calc R U . . .
C3 C 0.47779(19) 0.39516(13) 0.74190(10) 0.0120(3) Uani 1 1 d . . . . .
C4 C 0.4938(2) 0.33348(13) 0.66212(10) 0.0142(3) Uani 1 1 d . . . . .
H4A H 0.599519 0.322902 0.648455 0.017 Uiso 1 1 calc R U . . .
H4B H 0.444805 0.267642 0.667669 0.017 Uiso 1 1 calc R U . . .
C5 C 0.4168(2) 0.39731(14) 0.59599(10) 0.0141(3) Uani 1 1 d . . . . .
H5 H 0.483122 0.454642 0.581912 0.017 Uiso 1 1 calc R U . . .
C6 C 0.2780(2) 0.43877(14) 0.63960(11) 0.0165(3) Uani 1 1 d . . . . .
H6A H 0.255907 0.507465 0.620703 0.020 Uiso 1 1 calc R U . . .
H6B H 0.190813 0.395887 0.628678 0.020 Uiso 1 1 calc R U . . .
C16 C 0.3800(2) 0.34043(14) 0.51686(10) 0.0157(4) Uani 1 1 d . . . . .
H16 H 0.316750 0.281802 0.531616 0.019 Uiso 1 1 calc R U . . .
C17 C 0.5215(2) 0.30100(14) 0.47669(11) 0.0187(4) Uani 1 1 d . . . . .
H17A H 0.589242 0.357765 0.466202 0.022 Uiso 1 1 calc R U . . .
H17B H 0.571710 0.254924 0.515156 0.022 Uiso 1 1 calc R U . . .
O3 O 0.49439(18) 0.24949(11) 0.40103(8) 0.0222(3) Uani 1 1 d D . . . .
H3O H 0.448(3) 0.2009(19) 0.4146(18) 0.033 Uiso 1 1 d D U . . .
C18 C 0.2929(2) 0.40592(16) 0.45754(11) 0.0222(4) Uani 1 1 d . . . . .
H18A H 0.201256 0.428501 0.483912 0.033 Uiso 1 1 calc R U . . .
H18B H 0.268489 0.367301 0.408356 0.033 Uiso 1 1 calc R U . . .
H18C H 0.352845 0.464032 0.442219 0.033 Uiso 1 1 calc R U . . .
C7 C 0.31638(19) 0.43826(13) 0.73052(11) 0.0144(3) Uani 1 1 d . . . . .
O4 O 0.28070(16) 0.53002(10) 0.76909(9) 0.0209(3) Uani 1 1 d D . . . .
H4O H 0.352(3) 0.553(2) 0.7947(16) 0.031 Uiso 1 1 d D U . . .
C8 C 0.25992(19) 0.34616(14) 0.78209(11) 0.0179(4) Uani 1 1 d . . . . .
H8A H 0.184336 0.363326 0.823718 0.022 Uiso 1 1 calc R U . . .
H8B H 0.228227 0.288399 0.748506 0.022 Uiso 1 1 calc R U . . .
C9 C 0.41882(19) 0.33702(13) 0.81653(10) 0.0135(3) Uani 1 1 d . . . . .
H9 H 0.426185 0.381895 0.865330 0.016 Uiso 1 1 calc R U . . .
C10 C 0.5111(2) 0.24724(13) 0.83300(10) 0.0130(3) Uani 1 1 d . . . . .
O5 O 0.46498(14) 0.16186(10) 0.84261(8) 0.0183(3) Uani 1 1 d . . . . .
C11 C 0.67701(19) 0.27099(13) 0.83786(10) 0.0129(3) Uani 1 1 d . . . . .
H11 H 0.731797 0.211181 0.817107 0.016 Uiso 1 1 calc R U . . .
C12 C 0.73700(19) 0.36486(13) 0.78985(10) 0.0143(3) Uani 1 1 d . . . . .
H12 H 0.796992 0.342383 0.741774 0.017 Uiso 1 1 calc R U . . .
C13 C 0.8371(2) 0.42132(14) 0.85072(11) 0.0182(4) Uani 1 1 d . . . . .
H13 H 0.931893 0.443140 0.824546 0.022 Uiso 1 1 calc R U . . .
C14 C 0.8646(2) 0.35019(15) 0.92168(11) 0.0185(4) Uani 1 1 d . . . . .
H14A H 0.882489 0.387823 0.972928 0.022 Uiso 1 1 calc R U . . .
H14B H 0.951616 0.307268 0.910500 0.022 Uiso 1 1 calc R U . . .
C15 C 0.72323(19) 0.28679(13) 0.92882(11) 0.0145(3) Uani 1 1 d . . . . .
O6 O 0.60658(14) 0.34293(10) 0.96624(8) 0.0168(3) Uani 1 1 d D . . . .
H6O H 0.627(3) 0.3525(19) 1.0162(13) 0.025 Uiso 1 1 d D U . . .
C19 C 0.7469(2) 0.18889(14) 0.97456(11) 0.0186(4) Uani 1 1 d . . . . .
H19A H 0.768556 0.202993 1.032219 0.028 Uiso 1 1 calc R U . . .
H19B H 0.830229 0.152656 0.950113 0.028 Uiso 1 1 calc R U . . .
H19C H 0.657020 0.148016 0.970776 0.028 Uiso 1 1 calc R U . . .
O1W O 0.47854(17) 0.35609(13) 0.25677(9) 0.0279(3) Uani 1 1 d D . . . .
H1W1 H 0.484(4) 0.325(2) 0.3020(15) 0.042 Uiso 1 1 d D U . . .
H1W2 H 0.407(3) 0.396(2) 0.2643(19) 0.042 Uiso 1 1 d D U . . .
O2W O 0.66633(16) 0.38537(11) 0.13024(8) 0.0214(3) Uani 1 1 d D . . . .
H2W1 H 0.613(3) 0.373(2) 0.1714(15) 0.032 Uiso 1 1 d D U . . .
H2W2 H 0.753(3) 0.364(2) 0.1429(17) 0.032 Uiso 1 1 d D U . . .
O3W O 0.3494(2) 0.07558(12) 0.44269(10) 0.0359(4) Uani 1 1 d D . . . .
H3W1 H 0.368(4) 0.069(3) 0.4929(15) 0.054 Uiso 1 1 d D U . . .
H3W2 H 0.350(4) 0.0174(19) 0.418(2) 0.054 Uiso 1 1 d D U . . .


_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 1.340(2) . ?
O1 C13 1.469(2) . ?
C1 O2 1.210(2) . ?
C1 C2 1.520(2) . ?
C2 C3 1.521(2) . ?
C2 C12 1.549(2) . ?
C2 H2 1.0000 . ?
C3 C9 1.541(2) . ?
C3 C4 1.549(2) . ?
C3 C7 1.578(2) . ?
C4 C5 1.542(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C16 1.536(2) . ?
C5 C6 1.544(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.525(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C16 C18 1.525(3) . ?
C16 C17 1.529(3) . ?
C16 H16 1.0000 . ?
C17 O3 1.436(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
O3 H3O 0.80(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C7 O4 1.417(2) . ?
C7 C8 1.577(2) . ?
O4 H4O 0.82(2) . ?
C8 C9 1.545(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.486(2) . ?
C9 H9 1.0000 . ?
C10 O5 1.226(2) . ?
C10 C11 1.533(2) . ?
C11 C15 1.557(2) . ?
C11 C12 1.577(2) . ?
C11 H11 1.0000 . ?
C12 C13 1.541(2) . ?
C12 H12 1.0000 . ?
C13 C14 1.520(3) . ?
C13 H13 1.0000 . ?
C14 C15 1.536(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 O6 1.430(2) . ?
C15 C19 1.523(2) . ?
O6 H6O 0.85(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O1W H1W1 0.85(2) . ?
O1W H1W2 0.85(2) . ?
O2W H2W1 0.84(2) . ?
O2W H2W2 0.86(2) . ?
O3W H3W1 0.84(2) . ?
O3W H3W2 0.87(2) . ?

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 C13 111.53(14) . . ?
O2 C1 O1 120.48(17) . . ?
O2 C1 C2 128.76(17) . . ?
O1 C1 C2 110.76(15) . . ?
C1 C2 C3 117.03(14) . . ?
C1 C2 C12 102.49(14) . . ?
C3 C2 C12 109.07(14) . . ?
C1 C2 H2 109.3 . . ?
C3 C2 H2 109.3 . . ?
C12 C2 H2 109.3 . . ?
C2 C3 C9 110.52(13) . . ?
C2 C3 C4 109.79(14) . . ?
C9 C3 C4 115.36(14) . . ?
C2 C3 C7 131.85(15) . . ?
C9 C3 C7 87.64(13) . . ?
C4 C3 C7 100.48(13) . . ?
C5 C4 C3 104.57(13) . . ?
C5 C4 H4A 110.8 . . ?
C3 C4 H4A 110.8 . . ?
C5 C4 H4B 110.8 . . ?
C3 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
C16 C5 C4 114.32(15) . . ?
C16 C5 C6 113.02(15) . . ?
C4 C5 C6 103.99(13) . . ?
C16 C5 H5 108.4 . . ?
C4 C5 H5 108.4 . . ?
C6 C5 H5 108.4 . . ?
C7 C6 C5 105.26(14) . . ?
C7 C6 H6A 110.7 . . ?
C5 C6 H6A 110.7 . . ?
C7 C6 H6B 110.7 . . ?
C5 C6 H6B 110.7 . . ?
H6A C6 H6B 108.8 . . ?
C18 C16 C17 110.89(15) . . ?
C18 C16 C5 111.16(15) . . ?
C17 C16 C5 110.59(15) . . ?
C18 C16 H16 108.0 . . ?
C17 C16 H16 108.0 . . ?
C5 C16 H16 108.0 . . ?
O3 C17 C16 113.11(16) . . ?
O3 C17 H17A 109.0 . . ?
C16 C17 H17A 109.0 . . ?
O3 C17 H17B 109.0 . . ?
C16 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C17 O3 H3O 104(2) . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C7 C6 112.16(15) . . ?
O4 C7 C8 111.50(14) . . ?
C6 C7 C8 116.74(15) . . ?
O4 C7 C3 118.31(15) . . ?
C6 C7 C3 109.03(14) . . ?
C8 C7 C3 87.12(13) . . ?
C7 O4 H4O 112(2) . . ?
C9 C8 C7 87.50(13) . . ?
C9 C8 H8A 114.1 . . ?
C7 C8 H8A 114.1 . . ?
C9 C8 H8B 114.1 . . ?
C7 C8 H8B 114.1 . . ?
H8A C8 H8B 111.3 . . ?
C10 C9 C3 110.97(14) . . ?
C10 C9 C8 130.51(16) . . ?
C3 C9 C8 89.58(12) . . ?
C10 C9 H9 107.7 . . ?
C3 C9 H9 107.7 . . ?
C8 C9 H9 107.7 . . ?
O5 C10 C9 125.92(16) . . ?
O5 C10 C11 121.20(16) . . ?
C9 C10 C11 112.88(15) . . ?
C10 C11 C15 109.83(13) . . ?
C10 C11 C12 118.35(14) . . ?
C15 C11 C12 105.90(13) . . ?
C10 C11 H11 107.4 . . ?
C15 C11 H11 107.4 . . ?
C12 C11 H11 107.4 . . ?
C13 C12 C2 103.35(14) . . ?
C13 C12 C11 105.74(13) . . ?
C2 C12 C11 118.28(14) . . ?
C13 C12 H12 109.7 . . ?
C2 C12 H12 109.7 . . ?
C11 C12 H12 109.7 . . ?
O1 C13 C14 109.94(15) . . ?
O1 C13 C12 105.36(14) . . ?
C14 C13 C12 106.27(14) . . ?
O1 C13 H13 111.7 . . ?
C14 C13 H13 111.7 . . ?
C12 C13 H13 111.7 . . ?
C13 C14 C15 105.55(14) . . ?
C13 C14 H14A 110.6 . . ?
C15 C14 H14A 110.6 . . ?
C13 C14 H14B 110.6 . . ?
C15 C14 H14B 110.6 . . ?
H14A C14 H14B 108.8 . . ?
O6 C15 C19 110.20(15) . . ?
O6 C15 C14 110.70(14) . . ?
C19 C15 C14 113.33(14) . . ?
O6 C15 C11 106.36(13) . . ?
C19 C15 C11 112.85(15) . . ?
C14 C15 C11 103.01(14) . . ?
C15 O6 H6O 109.5(19) . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H1W1 O1W H1W2 103(3) . . ?
H2W1 O2W H2W2 105(3) . . ?
H3W1 O3W H3W2 111(3) . . ?

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
C13 O1 C1 O2 173.80(17) . . . . ?
C13 O1 C1 C2 -6.71(19) . . . . ?
O2 C1 C2 C3 -40.9(3) . . . . ?
O1 C1 C2 C3 139.63(15) . . . . ?
O2 C1 C2 C12 -160.19(19) . . . . ?
O1 C1 C2 C12 20.37(18) . . . . ?
C1 C2 C3 C9 -57.69(19) . . . . ?
C12 C2 C3 C9 57.98(18) . . . . ?
C1 C2 C3 C4 173.93(14) . . . . ?
C12 C2 C3 C4 -70.40(17) . . . . ?
C1 C2 C3 C7 48.3(2) . . . . ?
C12 C2 C3 C7 164.02(16) . . . . ?
C2 C3 C4 C5 -103.66(16) . . . . ?
C9 C3 C4 C5 130.68(15) . . . . ?
C7 C3 C4 C5 38.30(16) . . . . ?
C3 C4 C5 C16 -164.03(14) . . . . ?
C3 C4 C5 C6 -40.33(17) . . . . ?
C16 C5 C6 C7 149.27(15) . . . . ?
C4 C5 C6 C7 24.73(18) . . . . ?
C4 C5 C16 C18 175.24(16) . . . . ?
C6 C5 C16 C18 56.5(2) . . . . ?
C4 C5 C16 C17 -61.13(19) . . . . ?
C6 C5 C16 C17 -179.83(15) . . . . ?
C18 C16 C17 O3 -54.5(2) . . . . ?
C5 C16 C17 O3 -178.33(15) . . . . ?
C5 C6 C7 O4 132.31(15) . . . . ?
C5 C6 C7 C8 -97.27(17) . . . . ?
C5 C6 C7 C3 -0.71(19) . . . . ?
C2 C3 C7 O4 -24.0(3) . . . . ?
C9 C3 C7 O4 91.77(16) . . . . ?
C4 C3 C7 O4 -152.87(15) . . . . ?
C2 C3 C7 C6 105.8(2) . . . . ?
C9 C3 C7 C6 -138.51(15) . . . . ?
C4 C3 C7 C6 -23.14(17) . . . . ?
C2 C3 C7 C8 -136.90(18) . . . . ?
C9 C3 C7 C8 -21.17(12) . . . . ?
C4 C3 C7 C8 94.19(13) . . . . ?
O4 C7 C8 C9 -98.27(15) . . . . ?
C6 C7 C8 C9 131.00(15) . . . . ?
C3 C7 C8 C9 21.11(12) . . . . ?
C2 C3 C9 C10 -70.31(18) . . . . ?
C4 C3 C9 C10 54.98(19) . . . . ?
C7 C3 C9 C10 155.46(14) . . . . ?
C2 C3 C9 C8 155.83(15) . . . . ?
C4 C3 C9 C8 -78.88(16) . . . . ?
C7 C3 C9 C8 21.60(13) . . . . ?
C7 C8 C9 C10 -139.29(18) . . . . ?
C7 C8 C9 C3 -21.61(13) . . . . ?
C3 C9 C10 O5 -129.31(18) . . . . ?
C8 C9 C10 O5 -20.8(3) . . . . ?
C3 C9 C10 C11 51.09(19) . . . . ?
C8 C9 C10 C11 159.58(16) . . . . ?
O5 C10 C11 C15 -84.3(2) . . . . ?
C9 C10 C11 C15 95.36(17) . . . . ?
O5 C10 C11 C12 154.02(16) . . . . ?
C9 C10 C11 C12 -26.4(2) . . . . ?
C1 C2 C12 C13 -24.82(16) . . . . ?
C3 C2 C12 C13 -149.51(14) . . . . ?
C1 C2 C12 C11 91.56(17) . . . . ?
C3 C2 C12 C11 -33.1(2) . . . . ?
C10 C11 C12 C13 133.11(16) . . . . ?
C15 C11 C12 C13 9.42(18) . . . . ?
C10 C11 C12 C2 18.0(2) . . . . ?
C15 C11 C12 C2 -105.67(16) . . . . ?
C1 O1 C13 C14 -124.26(15) . . . . ?
C1 O1 C13 C12 -10.13(19) . . . . ?
C2 C12 C13 O1 21.90(17) . . . . ?
C11 C12 C13 O1 -103.05(15) . . . . ?
C2 C12 C13 C14 138.55(14) . . . . ?
C11 C12 C13 C14 13.60(18) . . . . ?
O1 C13 C14 C15 81.46(17) . . . . ?
C12 C13 C14 C15 -32.08(18) . . . . ?
C13 C14 C15 O6 -75.99(18) . . . . ?
C13 C14 C15 C19 159.61(15) . . . . ?
C13 C14 C15 C11 37.36(17) . . . . ?
C10 C11 C15 O6 -40.78(18) . . . . ?
C12 C11 C15 O6 88.10(15) . . . . ?
C10 C11 C15 C19 80.17(18) . . . . ?
C12 C11 C15 C19 -150.95(15) . . . . ?
C10 C11 C15 C14 -157.26(14) . . . . ?
C12 C11 C15 C14 -28.37(17) . . . . ?

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
_geom_hbond_publ_flag
O3 H3O O3W 0.80(2) 1.95(2) 2.755(2) 175(3) . yes
O4 H4O O2 0.82(2) 1.93(2) 2.737(2) 168(3) . yes
C9 H9 O6 1.00 2.37 2.976(2) 117.8 . yes
O6 H6O O2W 0.85(2) 1.95(2) 2.790(2) 175(3) 1_556 yes
O1W H1W1 O3 0.85(2) 1.91(2) 2.758(2) 178(3) . yes
O1W H1W2 O4 0.85(2) 1.96(2) 2.799(2) 169(3) 2_564 yes
O2W H2W1 O1W 0.84(2) 1.86(2) 2.701(2) 173(3) . yes
O2W H2W2 O5 0.86(2) 1.96(2) 2.804(2) 168(3) 4_556 yes
O3W H3W1 O1 0.84(2) 2.49(3) 3.184(2) 141(3) 3_646 yes
O3W H3W2 O2W 0.87(2) 1.94(2) 2.814(2) 175(4) 3_645 yes

_refine_diff_density_max         0.342
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.075

####################################################################### 
# 
# 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_V18139
_database_code_depnum_ccdc_archive 'CCDC 2239956'
loop_
_audit_author_name
_audit_author_address
'Michael Takase'
;California Institute of Technology
United States of America
;
_audit_update_record             
;
2023-02-05 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H38 O4 Si'
_chemical_formula_weight         430.64

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'
Si Si 0.2541 0.3302 '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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.3347(3)
_cell_length_b                   12.3768(5)
_cell_length_c                   30.9537(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2426.87(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9930
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      74.49

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.064
_shelx_estimated_absorpt_T_min   0.741
_shelx_estimated_absorpt_T_max   0.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6036
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   'SADABS-2016/2 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS HB micro-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.69
_diffrn_reflns_number            25153
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.855
_diffrn_reflns_theta_max         74.566
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4954
_reflns_number_gt                4717
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.999

_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       'APEX3 v2017.3-0 (Bruker-AXS, 2017)'
_computing_cell_refinement       'SAINT v8.38A (Bruker-AXS, 2013)'
_computing_data_reduction        'SAINT v8.38A (Bruker-AXS, 2013)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0453P)²+0.3967P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1955 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.001(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4954
_refine_ls_number_parameters     282
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0795
_refine_ls_wR_factor_gt          0.0776
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
C1 C 0.2853(3) 0.13486(15) 0.36625(6) 0.0174(4) Uani 1 1 d . . . . .
C15 C 0.4285(4) 0.05107(17) 0.38775(7) 0.0271(5) Uani 1 1 d . . . . .
H15A H 0.365506 -0.020865 0.384758 0.041 Uiso 1 1 calc R U . . .
H15B H 0.444262 0.068501 0.418468 0.041 Uiso 1 1 calc R U . . .
H15C H 0.567369 0.051901 0.373812 0.041 Uiso 1 1 calc R U . . .
O2 O 0.2611(2) 0.11288(11) 0.32178(4) 0.0193(3) Uani 1 1 d . . . . .
Si1 Si 0.17875(8) 0.00604(4) 0.29467(2) 0.01591(12) Uani 1 1 d . . . . .
C20 C 0.4027(3) -0.08720(17) 0.28222(7) 0.0244(4) Uani 1 1 d . . . . .
H20A H 0.510357 -0.048344 0.265604 0.037 Uiso 1 1 calc R U . . .
H20B H 0.350705 -0.148549 0.265273 0.037 Uiso 1 1 calc R U . . .
H20C H 0.464623 -0.113579 0.309250 0.037 Uiso 1 1 calc R U . . .
C21 C -0.0250(4) -0.07223(18) 0.32508(7) 0.0272(4) Uani 1 1 d . . . . .
H21A H 0.037180 -0.100688 0.351748 0.041 Uiso 1 1 calc R U . . .
H21B H -0.075227 -0.132306 0.307206 0.041 Uiso 1 1 calc R U . . .
H21C H -0.143717 -0.024747 0.332243 0.041 Uiso 1 1 calc R U . . .
C22 C 0.0679(3) 0.06652(16) 0.24350(7) 0.0218(4) Uani 1 1 d . . . . .
C23 C -0.1264(4) 0.1358(2) 0.25387(9) 0.0344(5) Uani 1 1 d . . . . .
H23A H -0.185588 0.164694 0.226993 0.052 Uiso 1 1 calc R U . . .
H23B H -0.084964 0.195741 0.272762 0.052 Uiso 1 1 calc R U . . .
H23C H -0.232610 0.091370 0.268475 0.052 Uiso 1 1 calc R U . . .
C24 C 0.2358(4) 0.13962(18) 0.22254(7) 0.0269(5) Uani 1 1 d . . . . .
H24A H 0.185797 0.163808 0.194184 0.040 Uiso 1 1 calc R U . . .
H24B H 0.367548 0.099004 0.219045 0.040 Uiso 1 1 calc R U . . .
H24C H 0.261073 0.202554 0.241042 0.040 Uiso 1 1 calc R U . . .
C25 C 0.0061(4) -0.02411(19) 0.21200(7) 0.0312(5) Uani 1 1 d . . . . .
H25A H -0.100985 -0.070355 0.225442 0.047 Uiso 1 1 calc R U . . .
H25B H 0.131003 -0.067397 0.205008 0.047 Uiso 1 1 calc R U . . .
H25C H -0.051276 0.007631 0.185478 0.047 Uiso 1 1 calc R U . . .
C2 C 0.0716(3) 0.14477(17) 0.39036(7) 0.0230(4) Uani 1 1 d . . . . .
H2A H -0.040824 0.169077 0.370375 0.028 Uiso 1 1 calc R U . . .
H2B H 0.029964 0.074325 0.402888 0.028 Uiso 1 1 calc R U . . .
C3 C 0.1072(3) 0.22891(17) 0.42631(6) 0.0212(4) Uani 1 1 d . . . . .
H3 H 0.105335 0.194534 0.455548 0.025 Uiso 1 1 calc R U . . .
O1 O -0.0488(2) 0.31407(12) 0.42307(5) 0.0237(3) Uani 1 1 d . . . . .
C4 C 0.0390(3) 0.41281(17) 0.42044(6) 0.0183(4) Uani 1 1 d . . . . .
O3 O -0.0697(2) 0.49218(13) 0.41864(5) 0.0262(3) Uani 1 1 d . . . . .
C5 C 0.2811(3) 0.40647(15) 0.42237(6) 0.0138(3) Uani 1 1 d . . . . .
C6 C 0.3546(3) 0.44713(15) 0.46854(6) 0.0154(4) Uani 1 1 d . . . . .
O4 O 0.5671(2) 0.41213(11) 0.47551(4) 0.0167(3) Uani 1 1 d D . . . .
H4O H 0.648(4) 0.429(2) 0.4552(8) 0.020 Uiso 1 1 d D U . . .
C16 C 0.2269(3) 0.39541(16) 0.50471(6) 0.0181(4) Uani 1 1 d . . . . .
H16A H 0.246420 0.316884 0.503990 0.027 Uiso 1 1 calc R U . . .
H16B H 0.077096 0.412515 0.500820 0.027 Uiso 1 1 calc R U . . .
H16C H 0.275134 0.423550 0.532616 0.027 Uiso 1 1 calc R U . . .
C7 C 0.3408(3) 0.57066(14) 0.47207(6) 0.0156(4) Uani 1 1 d . . . . .
H7A H 0.191372 0.592991 0.469126 0.019 Uiso 1 1 calc R U . . .
H7B H 0.389925 0.593123 0.501068 0.019 Uiso 1 1 calc R U . . .
C8 C 0.4719(3) 0.62851(15) 0.43789(6) 0.0160(4) Uani 1 1 d . . . . .
H8 H 0.619513 0.600367 0.439994 0.019 Uiso 1 1 calc R U . . .
C17 C 0.4820(3) 0.75026(16) 0.44256(6) 0.0183(4) Uani 1 1 d . . . . .
C18 C 0.3432(4) 0.80792(16) 0.46487(7) 0.0243(4) Uani 1 1 d . . . . .
H18A H 0.358587 0.884112 0.466863 0.029 Uiso 1 1 calc R U . . .
H18B H 0.228415 0.773037 0.478846 0.029 Uiso 1 1 calc R U . . .
C19 C 0.6667(4) 0.80167(16) 0.41981(7) 0.0241(4) Uani 1 1 d . . . . .
H19A H 0.668234 0.879392 0.425848 0.036 Uiso 1 1 calc R U . . .
H19B H 0.653685 0.790010 0.388609 0.036 Uiso 1 1 calc R U . . .
H19C H 0.798214 0.769048 0.430176 0.036 Uiso 1 1 calc R U . . .
C9 C 0.3849(3) 0.59563(16) 0.39331(6) 0.0200(4) Uani 1 1 d . . . . .
H9A H 0.239103 0.623316 0.390231 0.024 Uiso 1 1 calc R U . . .
H9B H 0.472314 0.629328 0.370469 0.024 Uiso 1 1 calc R U . . .
C10 C 0.3843(3) 0.47498(15) 0.38711(6) 0.0157(4) Uani 1 1 d . . . . .
C11 C 0.4656(3) 0.42919(16) 0.35174(6) 0.0203(4) Uani 1 1 d . . . . .
H11 H 0.542785 0.473158 0.332168 0.024 Uiso 1 1 calc R U . . .
C12 C 0.4409(3) 0.31435(16) 0.34185(6) 0.0185(4) Uani 1 1 d . . . . .
H12 H 0.475570 0.287678 0.313961 0.022 Uiso 1 1 calc R U . . .
C13 C 0.3699(3) 0.24775(15) 0.37204(6) 0.0151(3) Uani 1 1 d . . . . .
C14 C 0.3205(3) 0.28450(14) 0.41726(6) 0.0149(3) Uani 1 1 d . . . . .
H14 H 0.430987 0.259087 0.437988 0.018 Uiso 1 1 calc R U . . .


_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
C1 O2 1.412(2) . ?
C1 C13 1.507(3) . ?
C1 C15 1.530(3) . ?
C1 C2 1.551(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O2 Si1 1.6507(14) . ?
Si1 C21 1.868(2) . ?
Si1 C20 1.869(2) . ?
Si1 C22 1.887(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.534(3) . ?
C22 C25 1.537(3) . ?
C22 C24 1.540(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C2 C3 1.541(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O1 1.448(3) . ?
C3 C14 1.542(3) . ?
C3 H3 1.0000 . ?
O1 C4 1.345(3) . ?
C4 O3 1.201(3) . ?
C4 C5 1.537(2) . ?
C5 C10 1.529(2) . ?
C5 C14 1.538(2) . ?
C5 C6 1.585(2) . ?
C6 O4 1.430(2) . ?
C6 C16 1.522(3) . ?
C6 C7 1.535(2) . ?
O4 H4O 0.84(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C7 C8 1.524(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C17 1.515(3) . ?
C8 C9 1.540(3) . ?
C8 H8 1.0000 . ?
C17 C18 1.326(3) . ?
C17 C19 1.506(3) . ?
C18 H18A 0.9500 . ?
C18 H18B 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C9 C10 1.505(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.336(3) . ?
C11 C12 1.462(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.325(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.505(2) . ?
C14 H14 1.0000 . ?

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
O2 C1 C13 109.48(15) . . ?
O2 C1 C15 111.00(16) . . ?
C13 C1 C15 111.47(16) . . ?
O2 C1 C2 112.91(16) . . ?
C13 C1 C2 100.35(15) . . ?
C15 C1 C2 111.20(17) . . ?
C1 C15 H15A 109.5 . . ?
C1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 O2 Si1 133.20(12) . . ?
O2 Si1 C21 112.17(9) . . ?
O2 Si1 C20 111.08(9) . . ?
C21 Si1 C20 107.95(10) . . ?
O2 Si1 C22 103.08(8) . . ?
C21 Si1 C22 111.81(10) . . ?
C20 Si1 C22 110.76(10) . . ?
Si1 C20 H20A 109.5 . . ?
Si1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
Si1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
Si1 C21 H21A 109.5 . . ?
Si1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
Si1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C25 109.66(19) . . ?
C23 C22 C24 108.29(18) . . ?
C25 C22 C24 109.73(18) . . ?
C23 C22 Si1 110.17(15) . . ?
C25 C22 Si1 109.73(14) . . ?
C24 C22 Si1 109.24(14) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C3 C2 C1 105.86(16) . . ?
C3 C2 H2A 110.6 . . ?
C1 C2 H2A 110.6 . . ?
C3 C2 H2B 110.6 . . ?
C1 C2 H2B 110.6 . . ?
H2A C2 H2B 108.7 . . ?
O1 C3 C2 110.00(17) . . ?
O1 C3 C14 105.10(15) . . ?
C2 C3 C14 107.37(15) . . ?
O1 C3 H3 111.4 . . ?
C2 C3 H3 111.4 . . ?
C14 C3 H3 111.4 . . ?
C4 O1 C3 112.56(15) . . ?
O3 C4 O1 120.61(18) . . ?
O3 C4 C5 128.00(19) . . ?
O1 C4 C5 111.32(17) . . ?
C10 C5 C4 111.75(15) . . ?
C10 C5 C14 113.68(15) . . ?
C4 C5 C14 102.01(15) . . ?
C10 C5 C6 109.99(15) . . ?
C4 C5 C6 108.18(15) . . ?
C14 C5 C6 110.88(14) . . ?
O4 C6 C16 105.17(15) . . ?
O4 C6 C7 110.16(16) . . ?
C16 C6 C7 109.63(15) . . ?
O4 C6 C5 108.43(14) . . ?
C16 C6 C5 111.94(15) . . ?
C7 C6 C5 111.31(15) . . ?
C6 O4 H4O 112.7(19) . . ?
C6 C16 H16A 109.5 . . ?
C6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C8 C7 C6 112.79(15) . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C17 C8 C7 115.09(16) . . ?
C17 C8 C9 111.31(15) . . ?
C7 C8 C9 107.63(15) . . ?
C17 C8 H8 107.5 . . ?
C7 C8 H8 107.5 . . ?
C9 C8 H8 107.5 . . ?
C18 C17 C19 122.07(19) . . ?
C18 C17 C8 123.84(19) . . ?
C19 C17 C8 114.09(17) . . ?
C17 C18 H18A 120.0 . . ?
C17 C18 H18B 120.0 . . ?
H18A C18 H18B 120.0 . . ?
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 . . ?
C10 C9 C8 112.16(15) . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 121.61(17) . . ?
C11 C10 C5 120.96(17) . . ?
C9 C10 C5 117.41(16) . . ?
C10 C11 C12 122.87(18) . . ?
C10 C11 H11 118.6 . . ?
C12 C11 H11 118.6 . . ?
C13 C12 C11 119.56(17) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 122.60(17) . . ?
C12 C13 C1 127.85(17) . . ?
C14 C13 C1 108.49(15) . . ?
C13 C14 C5 115.21(15) . . ?
C13 C14 C3 102.49(15) . . ?
C5 C14 C3 106.08(15) . . ?
C13 C14 H14 110.9 . . ?
C5 C14 H14 110.9 . . ?
C3 C14 H14 110.9 . . ?

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
C13 C1 O2 Si1 179.54(13) . . . . ?
C15 C1 O2 Si1 56.1(2) . . . . ?
C2 C1 O2 Si1 -69.6(2) . . . . ?
C1 O2 Si1 C21 31.7(2) . . . . ?
C1 O2 Si1 C20 -89.25(19) . . . . ?
C1 O2 Si1 C22 152.10(17) . . . . ?
O2 Si1 C22 C23 -65.50(17) . . . . ?
C21 Si1 C22 C23 55.18(18) . . . . ?
C20 Si1 C22 C23 175.62(15) . . . . ?
O2 Si1 C22 C25 173.66(15) . . . . ?
C21 Si1 C22 C25 -65.66(18) . . . . ?
C20 Si1 C22 C25 54.79(18) . . . . ?
O2 Si1 C22 C24 53.33(15) . . . . ?
C21 Si1 C22 C24 174.01(14) . . . . ?
C20 Si1 C22 C24 -65.55(16) . . . . ?
O2 C1 C2 C3 -147.14(16) . . . . ?
C13 C1 C2 C3 -30.70(19) . . . . ?
C15 C1 C2 C3 87.3(2) . . . . ?
C1 C2 C3 O1 125.61(17) . . . . ?
C1 C2 C3 C14 11.8(2) . . . . ?
C2 C3 O1 C4 -125.15(17) . . . . ?
C14 C3 O1 C4 -9.8(2) . . . . ?
C3 O1 C4 O3 -178.16(17) . . . . ?
C3 O1 C4 C5 -0.9(2) . . . . ?
O3 C4 C5 C10 -50.1(3) . . . . ?
O1 C4 C5 C10 132.92(16) . . . . ?
O3 C4 C5 C14 -171.86(19) . . . . ?
O1 C4 C5 C14 11.1(2) . . . . ?
O3 C4 C5 C6 71.2(2) . . . . ?
O1 C4 C5 C6 -105.85(17) . . . . ?
C10 C5 C6 O4 -74.73(17) . . . . ?
C4 C5 C6 O4 162.96(15) . . . . ?
C14 C5 C6 O4 51.88(19) . . . . ?
C10 C5 C6 C16 169.70(15) . . . . ?
C4 C5 C6 C16 47.4(2) . . . . ?
C14 C5 C6 C16 -63.7(2) . . . . ?
C10 C5 C6 C7 46.6(2) . . . . ?
C4 C5 C6 C7 -75.7(2) . . . . ?
C14 C5 C6 C7 173.21(15) . . . . ?
O4 C6 C7 C8 62.5(2) . . . . ?
C16 C6 C7 C8 177.78(15) . . . . ?
C5 C6 C7 C8 -57.8(2) . . . . ?
C6 C7 C8 C17 -174.09(17) . . . . ?
C6 C7 C8 C9 61.2(2) . . . . ?
C7 C8 C17 C18 -20.2(3) . . . . ?
C9 C8 C17 C18 102.6(2) . . . . ?
C7 C8 C17 C19 159.28(17) . . . . ?
C9 C8 C17 C19 -77.9(2) . . . . ?
C17 C8 C9 C10 177.00(17) . . . . ?
C7 C8 C9 C10 -56.0(2) . . . . ?
C8 C9 C10 C11 -130.3(2) . . . . ?
C8 C9 C10 C5 51.3(2) . . . . ?
C4 C5 C10 C11 -103.3(2) . . . . ?
C14 C5 C10 C11 11.5(3) . . . . ?
C6 C5 C10 C11 136.48(19) . . . . ?
C4 C5 C10 C9 75.0(2) . . . . ?
C14 C5 C10 C9 -170.19(16) . . . . ?
C6 C5 C10 C9 -45.2(2) . . . . ?
C9 C10 C11 C12 -171.04(19) . . . . ?
C5 C10 C11 C12 7.2(3) . . . . ?
C10 C11 C12 C13 -12.7(3) . . . . ?
C11 C12 C13 C14 -2.5(3) . . . . ?
C11 C12 C13 C1 164.33(19) . . . . ?
O2 C1 C13 C12 -8.9(3) . . . . ?
C15 C1 C13 C12 114.3(2) . . . . ?
C2 C1 C13 C12 -127.8(2) . . . . ?
O2 C1 C13 C14 159.42(15) . . . . ?
C15 C1 C13 C14 -77.38(19) . . . . ?
C2 C1 C13 C14 40.45(18) . . . . ?
C12 C13 C14 C5 20.8(3) . . . . ?
C1 C13 C14 C5 -148.21(16) . . . . ?
C12 C13 C14 C3 135.51(19) . . . . ?
C1 C13 C14 C3 -33.52(19) . . . . ?
C10 C5 C14 C13 -24.1(2) . . . . ?
C4 C5 C14 C13 96.36(18) . . . . ?
C6 C5 C14 C13 -148.65(16) . . . . ?
C10 C5 C14 C3 -136.71(15) . . . . ?
C4 C5 C14 C3 -16.25(18) . . . . ?
C6 C5 C14 C3 98.75(17) . . . . ?
O1 C3 C14 C13 -104.81(16) . . . . ?
C2 C3 C14 C13 12.3(2) . . . . ?
O1 C3 C14 C5 16.37(18) . . . . ?
C2 C3 C14 C5 133.48(17) . . . . ?

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
_geom_hbond_publ_flag
C3 H3 O4 1.00 2.52 3.514(2) 171.9 4_456 yes
O4 H4O O1 0.84(2) 2.59(3) 3.167(2) 127(2) 1_655 yes
O4 H4O O3 0.84(2) 2.25(2) 3.062(2) 162(3) 1_655 yes
C7 H7A O3 0.99 2.59 3.231(2) 122.0 . yes

_refine_diff_density_max         0.271
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_V20018
_audit_block_doi                 10.5517/ccdc.csd.cc24qp3p
_database_code_depnum_ccdc_archive 'CCDC 1988002'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/jacs.0c02513 2020
loop_
_audit_author_name
_audit_author_address
'Michael Takase'
;California Institute of Technology
United States of America
;
_audit_update_record             
;
2020-03-03 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H22 O5'
_chemical_formula_weight         330.36

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

_cell_length_a                   6.1878(4)
_cell_length_b                   14.9676(14)
_cell_length_c                   17.511(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1621.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9979
_cell_measurement_theta_min      3.89
_cell_measurement_theta_max      74.52

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.800
_shelx_estimated_absorpt_T_min   0.715
_shelx_estimated_absorpt_T_max   0.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6083
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   'SADABS-2016/2 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS HB micro-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.69
_diffrn_reflns_number            14706
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.885
_diffrn_reflns_theta_max         74.514
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3306
_reflns_number_gt                3184
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_max     0.997
_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       'APEX3 v2019.1-0 (Bruker Nano, 2019)'
_computing_cell_refinement       'SAINT v8.40A (Bruker-AXS, 2013)'
_computing_data_reduction        'SAINT v8.40A (Bruker-AXS, 2013)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0474P)²+0.4838P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1307 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.00(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3306
_refine_ls_number_parameters     222
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0906
_refine_ls_wR_factor_gt          0.0889
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.1620(2) 0.57109(10) 0.53871(9) 0.0193(3) Uani 1 1 d . . . . .
C1 C 0.2687(3) 0.62348(13) 0.48936(11) 0.0162(4) Uani 1 1 d . . . . .
O2 O 0.1762(2) 0.67412(10) 0.44696(9) 0.0201(3) Uani 1 1 d . . . . .
C2 C 0.5129(3) 0.61353(13) 0.50023(11) 0.0158(4) Uani 1 1 d . . . . .
H2 H 0.561718 0.665173 0.532088 0.019 Uiso 1 1 calc R U . . .
C3 C 0.6351(3) 0.61832(13) 0.42623(11) 0.0142(4) Uani 1 1 d . . . . .
C4 C 0.6411(3) 0.70802(14) 0.38730(11) 0.0172(4) Uani 1 1 d . . . . .
H4A H 0.794034 0.724478 0.378479 0.021 Uiso 1 1 calc R U . . .
H4B H 0.578685 0.753027 0.422364 0.021 Uiso 1 1 calc R U . . .
C5 C 0.5192(3) 0.71333(14) 0.31007(12) 0.0177(4) Uani 1 1 d . . . . .
H5 H 0.362228 0.719812 0.322500 0.021 Uiso 1 1 calc R U . . .
C16 C 0.5851(4) 0.79742(15) 0.26742(12) 0.0222(5) Uani 1 1 d . . . . .
C17 C 0.4347(5) 0.86040(17) 0.25092(17) 0.0343(6) Uani 1 1 d . . . . .
H17A H 0.475425 0.913131 0.224365 0.041 Uiso 1 1 calc R U . . .
H17B H 0.288662 0.851801 0.265912 0.041 Uiso 1 1 calc R U . . .
C18 C 0.8117(4) 0.80924(19) 0.24483(16) 0.0336(6) Uani 1 1 d . . . . .
H18A H 0.826573 0.864538 0.215330 0.050 Uiso 1 1 calc R U . . .
H18B H 0.857497 0.758408 0.213484 0.050 Uiso 1 1 calc R U . . .
H18C H 0.902491 0.812669 0.290607 0.050 Uiso 1 1 calc R U . . .
C6 C 0.5415(4) 0.62781(15) 0.26091(12) 0.0213(4) Uani 1 1 d . . . . .
H6A H 0.446917 0.581066 0.282905 0.026 Uiso 1 1 calc R U . . .
H6B H 0.487377 0.641076 0.208923 0.026 Uiso 1 1 calc R U . . .
C7 C 0.7669(4) 0.59048(14) 0.25418(12) 0.0221(4) Uani 1 1 d . . . . .
O3 O 0.8577(4) 0.58480(14) 0.19321(10) 0.0380(5) Uani 1 1 d . . . . .
C8 C 0.8816(3) 0.55875(15) 0.32566(12) 0.0185(4) Uani 1 1 d . . . . .
H8A H 0.948118 0.500055 0.314431 0.022 Uiso 1 1 calc R U . . .
H8B H 1.000609 0.601030 0.336656 0.022 Uiso 1 1 calc R U . . .
C9 C 0.7470(3) 0.54909(14) 0.39740(11) 0.0152(4) Uani 1 1 d . . . . .
C10 C 0.7522(3) 0.46195(13) 0.43638(11) 0.0147(4) Uani 1 1 d . . . . .
O4 O 0.8720(2) 0.40158(10) 0.41410(9) 0.0192(3) Uani 1 1 d . . . . .
C11 C 0.6084(3) 0.44573(14) 0.50404(11) 0.0152(4) Uani 1 1 d . . . . .
H11 H 0.686852 0.405296 0.540065 0.018 Uiso 1 1 calc R U . . .
C12 C 0.3939(3) 0.39934(14) 0.48109(12) 0.0155(4) Uani 1 1 d . . . . .
O5 O 0.3102(2) 0.45185(9) 0.41894(8) 0.0150(3) Uani 1 1 d D . . . .
H5O H 0.181(4) 0.4353(19) 0.4117(16) 0.022 Uiso 1 1 d D U . . .
C19 C 0.4176(3) 0.30206(14) 0.45716(13) 0.0205(4) Uani 1 1 d . . . . .
H19A H 0.279660 0.280314 0.436905 0.031 Uiso 1 1 calc R U . . .
H19B H 0.459292 0.266042 0.501512 0.031 Uiso 1 1 calc R U . . .
H19C H 0.529161 0.297192 0.417646 0.031 Uiso 1 1 calc R U . . .
C13 C 0.2585(3) 0.41370(14) 0.55349(11) 0.0184(4) Uani 1 1 d . . . . .
H13A H 0.102672 0.406187 0.542475 0.022 Uiso 1 1 calc R U . . .
H13B H 0.300868 0.370839 0.593865 0.022 Uiso 1 1 calc R U . . .
C14 C 0.3075(3) 0.50928(14) 0.57796(12) 0.0187(4) Uani 1 1 d . . . . .
H14 H 0.297523 0.516164 0.634653 0.022 Uiso 1 1 calc R U . . .
C15 C 0.5399(3) 0.52980(14) 0.54865(11) 0.0164(4) Uani 1 1 d . . . . .
H15 H 0.640356 0.541095 0.592337 0.020 Uiso 1 1 calc R U . . .


_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 1.341(3) . ?
O1 C14 1.462(3) . ?
C1 O2 1.206(3) . ?
C1 C2 1.530(3) . ?
C2 C3 1.502(3) . ?
C2 C15 1.522(3) . ?
C2 H2 1.0000 . ?
C3 C9 1.345(3) . ?
C3 C4 1.506(3) . ?
C4 C5 1.551(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C16 1.519(3) . ?
C5 C6 1.549(3) . ?
C5 H5 1.0000 . ?
C16 C17 1.356(4) . ?
C16 C18 1.468(4) . ?
C17 H17A 0.9500 . ?
C17 H17B 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C6 C7 1.507(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O3 1.210(3) . ?
C7 C8 1.515(3) . ?
C8 C9 1.514(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.472(3) . ?
C10 O4 1.232(3) . ?
C10 C11 1.501(3) . ?
C11 C15 1.540(3) . ?
C11 C12 1.551(3) . ?
C11 H11 1.0000 . ?
C12 O5 1.439(2) . ?
C12 C19 1.522(3) . ?
C12 C13 1.535(3) . ?
O5 H5O 0.84(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C13 C14 1.524(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.558(3) . ?
C14 H14 1.0000 . ?
C15 H15 1.0000 . ?

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 C14 111.70(15) . . ?
O2 C1 O1 122.04(19) . . ?
O2 C1 C2 127.36(19) . . ?
O1 C1 C2 110.44(17) . . ?
C3 C2 C15 117.69(17) . . ?
C3 C2 C1 112.65(16) . . ?
C15 C2 C1 104.94(16) . . ?
C3 C2 H2 107.0 . . ?
C15 C2 H2 107.0 . . ?
C1 C2 H2 107.0 . . ?
C9 C3 C2 123.12(18) . . ?
C9 C3 C4 120.27(18) . . ?
C2 C3 C4 116.46(17) . . ?
C3 C4 C5 115.37(16) . . ?
C3 C4 H4A 108.4 . . ?
C5 C4 H4A 108.4 . . ?
C3 C4 H4B 108.4 . . ?
C5 C4 H4B 108.4 . . ?
H4A C4 H4B 107.5 . . ?
C16 C5 C6 112.80(17) . . ?
C16 C5 C4 109.91(17) . . ?
C6 C5 C4 113.52(17) . . ?
C16 C5 H5 106.7 . . ?
C6 C5 H5 106.7 . . ?
C4 C5 H5 106.7 . . ?
C17 C16 C18 121.0(2) . . ?
C17 C16 C5 119.8(2) . . ?
C18 C16 C5 119.3(2) . . ?
C16 C17 H17A 120.0 . . ?
C16 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C7 C6 C5 115.61(17) . . ?
C7 C6 H6A 108.4 . . ?
C5 C6 H6A 108.4 . . ?
C7 C6 H6B 108.4 . . ?
C5 C6 H6B 108.4 . . ?
H6A C6 H6B 107.4 . . ?
O3 C7 C6 121.7(2) . . ?
O3 C7 C8 119.3(2) . . ?
C6 C7 C8 119.01(18) . . ?
C9 C8 C7 117.25(18) . . ?
C9 C8 H8A 108.0 . . ?
C7 C8 H8A 108.0 . . ?
C9 C8 H8B 108.0 . . ?
C7 C8 H8B 108.0 . . ?
H8A C8 H8B 107.2 . . ?
C3 C9 C10 121.31(18) . . ?
C3 C9 C8 121.41(18) . . ?
C10 C9 C8 117.22(17) . . ?
O4 C10 C9 121.05(18) . . ?
O4 C10 C11 119.20(18) . . ?
C9 C10 C11 119.75(17) . . ?
C10 C11 C15 115.54(17) . . ?
C10 C11 C12 112.03(16) . . ?
C15 C11 C12 105.17(16) . . ?
C10 C11 H11 107.9 . . ?
C15 C11 H11 107.9 . . ?
C12 C11 H11 107.9 . . ?
O5 C12 C19 110.42(17) . . ?
O5 C12 C13 110.60(16) . . ?
C19 C12 C13 114.45(17) . . ?
O5 C12 C11 105.04(15) . . ?
C19 C12 C11 114.65(17) . . ?
C13 C12 C11 100.97(16) . . ?
C12 O5 H5O 107(2) . . ?
C12 C19 H19A 109.5 . . ?
C12 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C12 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C13 C12 104.79(16) . . ?
C14 C13 H13A 110.8 . . ?
C12 C13 H13A 110.8 . . ?
C14 C13 H13B 110.8 . . ?
C12 C13 H13B 110.8 . . ?
H13A C13 H13B 108.9 . . ?
O1 C14 C13 109.84(16) . . ?
O1 C14 C15 106.79(15) . . ?
C13 C14 C15 106.01(17) . . ?
O1 C14 H14 111.3 . . ?
C13 C14 H14 111.3 . . ?
C15 C14 H14 111.3 . . ?
C2 C15 C11 114.84(16) . . ?
C2 C15 C14 104.14(16) . . ?
C11 C15 C14 105.07(16) . . ?
C2 C15 H15 110.8 . . ?
C11 C15 H15 110.8 . . ?
C14 C15 H15 110.8 . . ?

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
C14 O1 C1 O2 174.04(18) . . . . ?
C14 O1 C1 C2 -10.2(2) . . . . ?
O2 C1 C2 C3 -40.7(3) . . . . ?
O1 C1 C2 C3 143.75(16) . . . . ?
O2 C1 C2 C15 -169.96(19) . . . . ?
O1 C1 C2 C15 14.5(2) . . . . ?
C15 C2 C3 C9 7.3(3) . . . . ?
C1 C2 C3 C9 -115.0(2) . . . . ?
C15 C2 C3 C4 -168.25(17) . . . . ?
C1 C2 C3 C4 69.4(2) . . . . ?
C9 C3 C4 C5 71.1(3) . . . . ?
C2 C3 C4 C5 -113.2(2) . . . . ?
C3 C4 C5 C16 -165.26(18) . . . . ?
C3 C4 C5 C6 -37.9(3) . . . . ?
C6 C5 C16 C17 114.0(2) . . . . ?
C4 C5 C16 C17 -118.3(2) . . . . ?
C6 C5 C16 C18 -66.2(3) . . . . ?
C4 C5 C16 C18 61.6(3) . . . . ?
C16 C5 C6 C7 79.8(2) . . . . ?
C4 C5 C6 C7 -46.1(3) . . . . ?
C5 C6 C7 O3 -118.2(2) . . . . ?
C5 C6 C7 C8 62.2(3) . . . . ?
O3 C7 C8 C9 -167.6(2) . . . . ?
C6 C7 C8 C9 12.0(3) . . . . ?
C2 C3 C9 C10 1.6(3) . . . . ?
C4 C3 C9 C10 177.02(16) . . . . ?
C2 C3 C9 C8 -175.38(18) . . . . ?
C4 C3 C9 C8 0.0(3) . . . . ?
C7 C8 C9 C3 -57.2(3) . . . . ?
C7 C8 C9 C10 125.7(2) . . . . ?
C3 C9 C10 O4 -172.57(19) . . . . ?
C8 C9 C10 O4 4.6(3) . . . . ?
C3 C9 C10 C11 7.9(3) . . . . ?
C8 C9 C10 C11 -174.98(17) . . . . ?
O4 C10 C11 C15 155.15(18) . . . . ?
C9 C10 C11 C15 -25.3(2) . . . . ?
O4 C10 C11 C12 -84.4(2) . . . . ?
C9 C10 C11 C12 95.1(2) . . . . ?
C10 C11 C12 O5 -50.5(2) . . . . ?
C15 C11 C12 O5 75.75(18) . . . . ?
C10 C11 C12 C19 70.9(2) . . . . ?
C15 C11 C12 C19 -162.86(17) . . . . ?
C10 C11 C12 C13 -165.57(16) . . . . ?
C15 C11 C12 C13 -39.29(18) . . . . ?
O5 C12 C13 C14 -69.4(2) . . . . ?
C19 C12 C13 C14 165.12(17) . . . . ?
C11 C12 C13 C14 41.41(18) . . . . ?
C1 O1 C14 C13 -112.91(18) . . . . ?
C1 O1 C14 C15 1.6(2) . . . . ?
C12 C13 C14 O1 86.82(18) . . . . ?
C12 C13 C14 C15 -28.20(19) . . . . ?
C3 C2 C15 C11 -24.3(2) . . . . ?
C1 C2 C15 C11 101.83(19) . . . . ?
C3 C2 C15 C14 -138.68(17) . . . . ?
C1 C2 C15 C14 -12.52(19) . . . . ?
C10 C11 C15 C2 32.7(2) . . . . ?
C12 C11 C15 C2 -91.33(19) . . . . ?
C10 C11 C15 C14 146.55(16) . . . . ?
C12 C11 C15 C14 22.47(19) . . . . ?
O1 C14 C15 C2 7.3(2) . . . . ?
C13 C14 C15 C2 124.43(17) . . . . ?
O1 C14 C15 C11 -113.76(17) . . . . ?
C13 C14 C15 C11 3.33(19) . . . . ?

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
_geom_hbond_publ_flag
C2 H2 O2 1.00 2.53 3.461(2) 154.0 4_566 yes
C8 H8B O2 0.99 2.47 3.289(3) 139.6 1_655 yes
O5 H5O O4 0.84(2) 1.98(2) 2.815(2) 170(3) 1_455 yes
C19 H19C O4 0.98 2.64 3.270(3) 122.7 . yes
C15 H15 O3 1.00 2.58 3.123(3) 113.7 2_665 yes

_refine_diff_density_max         0.657
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_D19016
_database_code_depnum_ccdc_archive 'CCDC 2239959'
loop_
_audit_author_name
_audit_author_address
'Michael Takase'
;California Institute of Technology
United States of America
;
_audit_update_record             
;
2023-02-05 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H30 O4.16 Si'
_chemical_formula_weight         413.21

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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   7.267(3)
_cell_length_b                   9.667(3)
_cell_length_c                   15.436(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.237(16)
_cell_angle_gamma                90
_cell_volume                     1070.3(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8747
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      32.34

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             443
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.138
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6535
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_process_details   'SADABS-2016/2 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 KAPPA'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            16781
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.495
_diffrn_reflns_theta_max         30.501
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_point_group_measured_fraction_full 0.955
_reflns_number_total             5995
_reflns_number_gt                5235
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_max     0.837
_reflns_Friedel_fraction_full    0.907

_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       'APEX3 v2017.3-0 (Bruker-AXS, 2017)'
_computing_cell_refinement       'SAINT v8.38A (Bruker-AXS, 2013)'
_computing_data_reduction        'SAINT v8.38A (Bruker-AXS, 2013)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0491P)²+0.1019P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1982 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.04(4)
_chemical_absolute_configuration abs
_refine_ls_number_reflns         5995
_refine_ls_number_parameters     280
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.0897
_refine_ls_wR_factor_gt          0.0861
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_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
Si1 Si 0.43864(8) 0.62786(6) 0.85224(3) 0.01487(13) Uani 1 1 d . . . . .
C1 C 0.3245(3) 0.4685(2) 0.79731(12) 0.0121(4) Uani 1 1 d . . . . .
C2 C 0.3535(3) 0.3370(2) 0.85474(13) 0.0166(4) Uani 1 1 d . . . . .
H2A H 0.485973 0.326809 0.881626 0.020 Uiso 1 1 calc R U . . .
H2B H 0.276019 0.340001 0.901914 0.020 Uiso 1 1 calc R U . . .
C3 C 0.2928(3) 0.2185(2) 0.79093(13) 0.0155(4) Uani 1 1 d . . . . .
H3A H 0.342417 0.128679 0.815110 0.019 Uiso 1 1 calc R U . . .
H3B H 0.155263 0.212741 0.776455 0.019 Uiso 1 1 calc R U . . .
C4 C 0.3789(3) 0.2600(2) 0.71127(13) 0.0123(4) Uani 1 1 d . . . . .
H4A H 0.318485 0.209727 0.658399 0.015 Uiso 1 1 calc R U . . .
H4B H 0.513984 0.238979 0.720901 0.015 Uiso 1 1 calc R U . . .
C5 C 0.3459(3) 0.4173(2) 0.70012(12) 0.0101(4) Uani 1 1 d . . . . .
C6 C 0.4859(3) 0.4923(2) 0.64880(13) 0.0121(4) Uani 1 1 d . . . . .
H6 H 0.564679 0.552940 0.692367 0.015 Uiso 0.834(7) 1 calc R U P A 1
O6B O 0.6250(11) 0.5648(9) 0.7055(5) 0.009(3) Uani 0.166(7) 1 d . . P A 2
H6OB H 0.698514 0.602591 0.675863 0.09(9) Uiso 0.166(7) 1 calc R . P A 2
C7 C 0.6204(3) 0.3975(2) 0.61030(15) 0.0171(4) Uani 1 1 d . . . . .
O1 O 0.6138(2) 0.41825(17) 0.52379(10) 0.0201(3) Uani 1 1 d . . . . .
O2 O 0.7296(2) 0.31571(17) 0.64887(12) 0.0245(4) Uani 1 1 d . . . . .
C8 C 0.5001(3) 0.5372(2) 0.49254(14) 0.0169(4) Uani 1 1 d . . . . .
H8 H 0.578549 0.612269 0.472857 0.020 Uiso 1 1 calc R U . . .
C9 C 0.3445(3) 0.4958(2) 0.41866(13) 0.0179(4) Uani 1 1 d . . . . .
H9A H 0.317676 0.571769 0.375446 0.021 Uiso 1 1 calc R U . . .
H9B H 0.380055 0.412358 0.388052 0.021 Uiso 1 1 calc R U . . .
C10 C 0.1752(3) 0.4665(2) 0.46257(13) 0.0128(4) Uani 1 1 d . . . . .
C18 C -0.0089(3) 0.4728(2) 0.40016(14) 0.0193(4) Uani 1 1 d . . . . .
H18A H -0.008111 0.404789 0.353146 0.029 Uiso 1 1 calc R U . . .
H18B H -0.026025 0.565697 0.374695 0.029 Uiso 1 1 calc R U . . .
H18C H -0.111333 0.452042 0.432365 0.029 Uiso 1 1 calc R U . . .
O3 O 0.1978(2) 0.33708(15) 0.50783(9) 0.0148(3) Uani 1 1 d D . . . .
H3O H 0.163(4) 0.274(2) 0.4749(16) 0.022 Uiso 1 1 d D U . . .
C11 C 0.1954(3) 0.5803(2) 0.53427(12) 0.0123(4) Uani 1 1 d . . . . .
H11 H 0.158120 0.670543 0.504902 0.015 Uiso 1 1 calc R U . . .
C12 C 0.4054(3) 0.5873(2) 0.57061(13) 0.0128(4) Uani 1 1 d . . . . .
H12 H 0.441822 0.685341 0.585079 0.015 Uiso 1 1 calc R U . . .
C13 C 0.0749(3) 0.5568(2) 0.60313(12) 0.0117(4) Uani 1 1 d . . . . .
O4 O -0.06908(19) 0.62231(17) 0.60408(9) 0.0168(3) Uani 1 1 d . . . . .
C14 C 0.1345(3) 0.4496(2) 0.67147(12) 0.0106(4) Uani 1 1 d . . . . .
H14 H 0.064650 0.361704 0.655546 0.013 Uiso 1 1 calc R U . . .
C15 C 0.1116(3) 0.4936(2) 0.76515(12) 0.0140(4) Uani 1 1 d . . . . .
H15A H 0.029709 0.431376 0.792843 0.017 Uiso 1 1 calc R U . . .
H15B H 0.073341 0.591331 0.769471 0.017 Uiso 1 1 calc R U . . .
C16 C 0.6926(3) 0.6088(3) 0.89006(16) 0.0268(5) Uani 1 1 d . . . . .
H16A H 0.753051 0.578701 0.840911 0.040 Uiso 1 1 calc R U . . .
H16B H 0.714053 0.539743 0.937086 0.040 Uiso 1 1 calc R U . . .
H16C H 0.744874 0.697830 0.912184 0.040 Uiso 1 1 calc R U . . .
C17 C 0.3947(4) 0.7835(3) 0.77909(16) 0.0264(5) Uani 1 1 d . . . . .
H17A H 0.414812 0.867725 0.814659 0.040 Uiso 1 1 calc R U . . .
H17B H 0.265861 0.781482 0.748260 0.040 Uiso 1 1 calc R U . . .
H17C H 0.480480 0.782450 0.736161 0.040 Uiso 1 1 calc R U . . .
C21 C 0.3208(3) 0.6548(2) 0.95084(14) 0.0186(5) Uani 1 1 d . . . . .
C22 C 0.1903(3) 0.7607(3) 0.95466(16) 0.0251(5) Uani 1 1 d . . . . .
H22 H 0.162200 0.822699 0.906603 0.030 Uiso 1 1 calc R U . . .
C23 C 0.1014(4) 0.7768(3) 1.02733(19) 0.0348(7) Uani 1 1 d . . . . .
H23 H 0.013977 0.849501 1.028726 0.042 Uiso 1 1 calc R U . . .
C24 C 0.1401(4) 0.6871(3) 1.09743(19) 0.0367(7) Uani 1 1 d . . . . .
H24 H 0.079214 0.697942 1.147060 0.044 Uiso 1 1 calc R U . . .
C25 C 0.2668(4) 0.5819(3) 1.09547(16) 0.0303(6) Uani 1 1 d . . . . .
H25 H 0.292397 0.519732 1.143569 0.036 Uiso 1 1 calc R U . . .
C26 C 0.3574(3) 0.5662(3) 1.02354(14) 0.0226(5) Uani 1 1 d . . . . .
H26 H 0.446138 0.494063 1.023516 0.027 Uiso 1 1 calc R U . . .


_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
Si1 C16 1.853(2) . ?
Si1 C17 1.877(3) . ?
Si1 C21 1.881(2) . ?
Si1 C1 1.886(2) . ?
C1 C2 1.545(3) . ?
C1 C15 1.566(3) . ?
C1 C5 1.611(3) . ?
C2 C3 1.529(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.520(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.545(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C14 1.561(3) . ?
C5 C6 1.564(3) . ?
C6 O6B 1.412(8) . ?
C6 C7 1.529(3) . ?
C6 C12 1.554(3) . ?
C6 H6 1.0000 . ?
O6B H6OB 0.8400 . ?
C7 O2 1.207(3) . ?
C7 O1 1.343(3) . ?
O1 C8 1.452(3) . ?
C8 C9 1.525(3) . ?
C8 C12 1.558(3) . ?
C8 H8 1.0000 . ?
C9 C10 1.524(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 O3 1.430(2) . ?
C10 C18 1.519(3) . ?
C10 C11 1.551(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O3 H3O 0.81(2) . ?
C11 C13 1.499(3) . ?
C11 C12 1.541(3) . ?
C11 H11 1.0000 . ?
C12 H12 1.0000 . ?
C13 O4 1.225(2) . ?
C13 C14 1.492(3) . ?
C14 C15 1.542(3) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C21 C26 1.403(3) . ?
C21 C22 1.403(3) . ?
C22 C23 1.390(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.380(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.375(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.387(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

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
C16 Si1 C17 109.50(13) . . ?
C16 Si1 C21 108.58(11) . . ?
C17 Si1 C21 108.67(11) . . ?
C16 Si1 C1 113.85(11) . . ?
C17 Si1 C1 111.37(10) . . ?
C21 Si1 C1 104.63(10) . . ?
C2 C1 C15 110.28(17) . . ?
C2 C1 C5 104.92(16) . . ?
C15 C1 C5 89.47(14) . . ?
C2 C1 Si1 113.87(14) . . ?
C15 C1 Si1 110.89(13) . . ?
C5 C1 Si1 124.62(14) . . ?
C3 C2 C1 104.36(16) . . ?
C3 C2 H2A 110.9 . . ?
C1 C2 H2A 110.9 . . ?
C3 C2 H2B 110.9 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
C4 C3 C2 102.09(17) . . ?
C4 C3 H3A 111.4 . . ?
C2 C3 H3A 111.4 . . ?
C4 C3 H3B 111.4 . . ?
C2 C3 H3B 111.4 . . ?
H3A C3 H3B 109.2 . . ?
C3 C4 C5 105.86(16) . . ?
C3 C4 H4A 110.6 . . ?
C5 C4 H4A 110.6 . . ?
C3 C4 H4B 110.6 . . ?
C5 C4 H4B 110.6 . . ?
H4A C4 H4B 108.7 . . ?
C4 C5 C14 110.87(16) . . ?
C4 C5 C6 114.26(16) . . ?
C14 C5 C6 117.03(16) . . ?
C4 C5 C1 103.58(15) . . ?
C14 C5 C1 87.97(14) . . ?
C6 C5 C1 119.85(16) . . ?
O6B C6 C7 95.7(4) . . ?
O6B C6 C12 109.3(4) . . ?
C7 C6 C12 103.69(16) . . ?
O6B C6 C5 112.1(4) . . ?
C7 C6 C5 115.31(17) . . ?
C12 C6 C5 118.24(16) . . ?
C7 C6 H6 106.2 . . ?
C12 C6 H6 106.2 . . ?
C5 C6 H6 106.2 . . ?
C6 O6B H6OB 109.5 . . ?
O2 C7 O1 120.3(2) . . ?
O2 C7 C6 127.7(2) . . ?
O1 C7 C6 111.93(18) . . ?
C7 O1 C8 112.11(17) . . ?
O1 C8 C9 110.79(18) . . ?
O1 C8 C12 106.70(16) . . ?
C9 C8 C12 107.08(18) . . ?
O1 C8 H8 110.7 . . ?
C9 C8 H8 110.7 . . ?
C12 C8 H8 110.7 . . ?
C10 C9 C8 105.72(17) . . ?
C10 C9 H9A 110.6 . . ?
C8 C9 H9A 110.6 . . ?
C10 C9 H9B 110.6 . . ?
C8 C9 H9B 110.6 . . ?
H9A C9 H9B 108.7 . . ?
O3 C10 C18 111.44(17) . . ?
O3 C10 C9 110.04(17) . . ?
C18 C10 C9 113.72(17) . . ?
O3 C10 C11 106.37(15) . . ?
C18 C10 C11 113.38(17) . . ?
C9 C10 C11 101.23(16) . . ?
C10 C18 H18A 109.5 . . ?
C10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 O3 H3O 110.9(19) . . ?
C13 C11 C12 113.93(16) . . ?
C13 C11 C10 113.52(17) . . ?
C12 C11 C10 105.39(16) . . ?
C13 C11 H11 107.9 . . ?
C12 C11 H11 107.9 . . ?
C10 C11 H11 107.9 . . ?
C11 C12 C6 118.97(16) . . ?
C11 C12 C8 103.86(16) . . ?
C6 C12 C8 105.05(16) . . ?
C11 C12 H12 109.5 . . ?
C6 C12 H12 109.5 . . ?
C8 C12 H12 109.5 . . ?
O4 C13 C14 120.14(18) . . ?
O4 C13 C11 121.80(18) . . ?
C14 C13 C11 118.06(17) . . ?
C13 C14 C15 114.11(17) . . ?
C13 C14 C5 119.99(17) . . ?
C15 C14 C5 92.24(14) . . ?
C13 C14 H14 109.7 . . ?
C15 C14 H14 109.7 . . ?
C5 C14 H14 109.7 . . ?
C14 C15 C1 90.25(15) . . ?
C14 C15 H15A 113.6 . . ?
C1 C15 H15A 113.6 . . ?
C14 C15 H15B 113.6 . . ?
C1 C15 H15B 113.6 . . ?
H15A C15 H15B 110.9 . . ?
Si1 C16 H16A 109.5 . . ?
Si1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
Si1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Si1 C17 H17A 109.5 . . ?
Si1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
Si1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C26 C21 C22 117.0(2) . . ?
C26 C21 Si1 120.69(17) . . ?
C22 C21 Si1 122.26(19) . . ?
C23 C22 C21 121.4(3) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C24 C23 C22 120.0(3) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C25 C24 C23 120.0(2) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 120.3(3) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C21 121.4(2) . . ?
C25 C26 H26 119.3 . . ?
C21 C26 H26 119.3 . . ?

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
C16 Si1 C1 C2 56.33(18) . . . . ?
C17 Si1 C1 C2 -179.28(15) . . . . ?
C21 Si1 C1 C2 -62.05(17) . . . . ?
C16 Si1 C1 C15 -178.59(14) . . . . ?
C17 Si1 C1 C15 -54.20(17) . . . . ?
C21 Si1 C1 C15 63.02(15) . . . . ?
C16 Si1 C1 C5 -74.03(18) . . . . ?
C17 Si1 C1 C5 50.4(2) . . . . ?
C21 Si1 C1 C5 167.59(16) . . . . ?
C15 C1 C2 C3 67.9(2) . . . . ?
C5 C1 C2 C3 -27.2(2) . . . . ?
Si1 C1 C2 C3 -166.73(14) . . . . ?
C1 C2 C3 C4 42.6(2) . . . . ?
C2 C3 C4 C5 -42.0(2) . . . . ?
C3 C4 C5 C14 -68.47(19) . . . . ?
C3 C4 C5 C6 156.67(16) . . . . ?
C3 C4 C5 C1 24.6(2) . . . . ?
C2 C1 C5 C4 1.8(2) . . . . ?
C15 C1 C5 C4 -109.09(16) . . . . ?
Si1 C1 C5 C4 135.63(15) . . . . ?
C2 C1 C5 C14 112.77(17) . . . . ?
C15 C1 C5 C14 1.90(15) . . . . ?
Si1 C1 C5 C14 -113.38(16) . . . . ?
C2 C1 C5 C6 -126.96(19) . . . . ?
C15 C1 C5 C6 122.16(18) . . . . ?
Si1 C1 C5 C6 6.9(2) . . . . ?
C4 C5 C6 O6B -102.5(4) . . . . ?
C14 C5 C6 O6B 125.6(4) . . . . ?
C1 C5 C6 O6B 21.3(4) . . . . ?
C4 C5 C6 C7 5.6(2) . . . . ?
C14 C5 C6 C7 -126.37(19) . . . . ?
C1 C5 C6 C7 129.33(19) . . . . ?
C4 C5 C6 C12 129.03(18) . . . . ?
C14 C5 C6 C12 -2.9(2) . . . . ?
C1 C5 C6 C12 -107.2(2) . . . . ?
O6B C6 C7 O2 60.3(4) . . . . ?
C12 C6 C7 O2 171.8(2) . . . . ?
C5 C6 C7 O2 -57.4(3) . . . . ?
O6B C6 C7 O1 -116.5(4) . . . . ?
C12 C6 C7 O1 -5.0(2) . . . . ?
C5 C6 C7 O1 125.80(18) . . . . ?
O2 C7 O1 C8 -169.35(19) . . . . ?
C6 C7 O1 C8 7.8(2) . . . . ?
C7 O1 C8 C9 -123.23(18) . . . . ?
C7 O1 C8 C12 -7.0(2) . . . . ?
O1 C8 C9 C10 94.2(2) . . . . ?
C12 C8 C9 C10 -21.8(2) . . . . ?
C8 C9 C10 O3 -74.5(2) . . . . ?
C8 C9 C10 C18 159.71(18) . . . . ?
C8 C9 C10 C11 37.8(2) . . . . ?
O3 C10 C11 C13 -50.7(2) . . . . ?
C18 C10 C11 C13 72.2(2) . . . . ?
C9 C10 C11 C13 -165.64(17) . . . . ?
O3 C10 C11 C12 74.70(19) . . . . ?
C18 C10 C11 C12 -162.48(17) . . . . ?
C9 C10 C11 C12 -40.28(19) . . . . ?
C13 C11 C12 C6 36.0(2) . . . . ?
C10 C11 C12 C6 -89.1(2) . . . . ?
C13 C11 C12 C8 152.21(17) . . . . ?
C10 C11 C12 C8 27.10(19) . . . . ?
O6B C6 C12 C11 -142.6(4) . . . . ?
C7 C6 C12 C11 116.25(18) . . . . ?
C5 C6 C12 C11 -12.8(3) . . . . ?
O6B C6 C12 C8 101.8(4) . . . . ?
C7 C6 C12 C8 0.6(2) . . . . ?
C5 C6 C12 C8 -128.44(18) . . . . ?
O1 C8 C12 C11 -122.18(17) . . . . ?
C9 C8 C12 C11 -3.5(2) . . . . ?
O1 C8 C12 C6 3.5(2) . . . . ?
C9 C8 C12 C6 122.15(18) . . . . ?
C12 C11 C13 O4 135.85(19) . . . . ?
C10 C11 C13 O4 -103.5(2) . . . . ?
C12 C11 C13 C14 -44.4(2) . . . . ?
C10 C11 C13 C14 76.2(2) . . . . ?
O4 C13 C14 C15 -42.7(3) . . . . ?
C11 C13 C14 C15 137.55(18) . . . . ?
O4 C13 C14 C5 -150.63(19) . . . . ?
C11 C13 C14 C5 29.6(3) . . . . ?
C4 C5 C14 C13 -138.52(18) . . . . ?
C6 C5 C14 C13 -5.0(3) . . . . ?
C1 C5 C14 C13 117.72(18) . . . . ?
C4 C5 C14 C15 101.83(17) . . . . ?
C6 C5 C14 C15 -124.68(17) . . . . ?
C1 C5 C14 C15 -1.93(15) . . . . ?
C13 C14 C15 C1 -122.46(17) . . . . ?
C5 C14 C15 C1 1.98(16) . . . . ?
C2 C1 C15 C14 -107.64(17) . . . . ?
C5 C1 C15 C14 -1.92(15) . . . . ?
Si1 C1 C15 C14 125.28(14) . . . . ?
C16 Si1 C21 C26 -49.7(2) . . . . ?
C17 Si1 C21 C26 -168.77(18) . . . . ?
C1 Si1 C21 C26 72.18(19) . . . . ?
C16 Si1 C21 C22 131.85(19) . . . . ?
C17 Si1 C21 C22 12.8(2) . . . . ?
C1 Si1 C21 C22 -106.24(19) . . . . ?
C26 C21 C22 C23 -0.1(3) . . . . ?
Si1 C21 C22 C23 178.40(18) . . . . ?
C21 C22 C23 C24 -0.3(4) . . . . ?
C22 C23 C24 C25 0.1(4) . . . . ?
C23 C24 C25 C26 0.6(4) . . . . ?
C24 C25 C26 C21 -1.0(4) . . . . ?
C22 C21 C26 C25 0.8(3) . . . . ?
Si1 C21 C26 C25 -177.75(18) . . . . ?

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
_geom_hbond_publ_flag
C9 H9A O2 0.99 2.40 3.280(3) 147.2 2_656 yes
C18 H18C O1 0.98 2.64 3.622(3) 175.1 1_455 yes
O3 H3O O4 0.81(2) 1.96(2) 2.766(2) 177(3) 2_546 yes
C14 H14 O2 1.00 2.46 3.182(3) 128.6 1_455 yes

_refine_diff_density_max         0.316
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_d20010
_audit_block_doi                 10.5517/ccdc.csd.cc24qnyh
_database_code_depnum_ccdc_archive 'CCDC 1987997'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/jacs.0c02513 2020
loop_
_audit_author_name
_audit_author_address
'Lawrence Henling'
;California Institute of Technology
United States of America
;
_audit_update_record             
;
2020-03-03 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;
_audit_creation_date             2020-02-22
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003),
 SHELXL-2018/3, and manual edit
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H34 O4 Si'
_chemical_formula_sum            'C27 H34 O4 Si'
_chemical_formula_weight         450.63
_chemical_absolute_configuration ad
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.9085(14)
_cell_length_b                   10.3765(19)
_cell_length_c                   17.058(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.920(7)
_cell_angle_gamma                90
_cell_volume                     1222.7(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9732
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.78
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0605 before and 0.0555 after correction.
The Ratio of minimum to maximum transmission is 0.9658.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             484
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 1.00 0.0080
0.00 0.00 -1.00 0.0190
1.00 -1.00 -1.00 0.1780
-1.00 -1.00 0.00 0.1120
-1.00 0.00 1.00 0.1440
1.00 0.00 -1.00 0.1510
0.00 -1.00 0.00 0.1020
0.00 1.00 0.00 0.0770
1.00 8.00 -1.00 0.0570

_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            76181
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.803
_diffrn_reflns_theta_min         2.297
_diffrn_ambient_temperature      100
_diffrn_detector                 'CMOS Area Detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker PHOTON 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Kappa'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Triumph focusing graphite'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_type              'XRD C-TECH Long Fine Focus'
_diffrn_source_voltage           50.0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.874
_reflns_number_gt                7343
_reflns_number_total             8271
_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_data_collection       
'BIS 2018.9.0.2/05-Oct-2018 & APEX3_2019.1-0 (Bruker-AXS, 2018)'
_computing_cell_refinement       'SAINT V8.40A (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.40A (Bruker-AXS, 2016)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND 3 (Crystal Impact, 1999)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 3000 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_abs_structure_Hooft   0.03(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         8271
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.035
_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)+(0.0453P)²+0.2224P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0865
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C16(H16), C18(H18), C22(H22), C24(H24), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C15(H15A,H15B), C21(H21A,H21B), C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C6(H6)
2.d X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C14(H14A,H14B,H14C), C20(H20A,H20B,H20C)
2.f Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Si1 Si 0.84284(6) 0.63687(4) 0.52641(3) 0.01312(10) Uani 1 1 d . . . . .
O1 O 1.11852(17) 0.29694(12) 0.07683(7) 0.0152(2) Uani 1 1 d . . . . .
O2 O 0.79881(18) 0.57572(12) 0.00914(7) 0.0147(2) Uani 1 1 d . . . . .
H2 H 0.815678 0.641601 -0.018543 0.022 Uiso 1 1 calc R U . . .
O3 O 0.38726(17) 0.51229(12) 0.01471(7) 0.0144(2) Uani 1 1 d . . . . .
O4 O 0.38244(19) 0.62608(14) 0.12393(8) 0.0225(3) Uani 1 1 d . . . . .
C1 C 0.8286(3) 0.50711(17) 0.60272(10) 0.0171(3) Uani 1 1 d . . . . .
C2 C 0.9930(3) 0.44260(19) 0.63105(11) 0.0232(4) Uani 1 1 d . . . . .
H2A H 1.115796 0.463096 0.610129 0.028 Uiso 1 1 calc R U . . .
C3 C 0.9807(4) 0.3490(2) 0.68921(13) 0.0321(5) Uani 1 1 d . . . . .
H3 H 1.094573 0.306274 0.707272 0.039 Uiso 1 1 calc R U . . .
C4 C 0.8048(4) 0.3182(2) 0.72063(12) 0.0351(6) Uani 1 1 d . . . . .
H4 H 0.796866 0.254073 0.760189 0.042 Uiso 1 1 calc R U . . .
C5 C 0.6396(4) 0.3808(2) 0.69452(13) 0.0352(5) Uani 1 1 d . . . . .
H5 H 0.517893 0.360358 0.716462 0.042 Uiso 1 1 calc R U . . .
C6 C 0.6516(3) 0.4739(2) 0.63599(12) 0.0262(4) Uani 1 1 d . . . . .
H6 H 0.536816 0.515804 0.618211 0.031 Uiso 1 1 calc R U . . .
C7 C 1.1022(3) 0.66249(18) 0.50382(11) 0.0186(4) Uani 1 1 d . . . . .
H7A H 1.154987 0.584167 0.480219 0.028 Uiso 1 1 calc R U . . .
H7B H 1.174184 0.682324 0.552288 0.028 Uiso 1 1 calc R U . . .
H7C H 1.114101 0.734478 0.467027 0.028 Uiso 1 1 calc R U . . .
C8 C 0.7300(3) 0.78492(19) 0.56752(12) 0.0216(4) Uani 1 1 d . . . . .
H8A H 0.730702 0.853519 0.528042 0.032 Uiso 1 1 calc R U . . .
H8B H 0.803810 0.812874 0.614037 0.032 Uiso 1 1 calc R U . . .
H8C H 0.596325 0.766182 0.582103 0.032 Uiso 1 1 calc R U . . .
C9 C 0.7099(2) 0.58674(17) 0.43479(10) 0.0146(3) Uani 1 1 d . . . . .
C10 C 0.5423(2) 0.6434(2) 0.41591(10) 0.0198(3) Uani 1 1 d . . . . .
H10A H 0.474418 0.619081 0.369327 0.024 Uiso 1 1 calc R U . . .
H10B H 0.490660 0.707986 0.449035 0.024 Uiso 1 1 calc R U . . .
C11 C 0.7990(3) 0.48322(19) 0.38422(10) 0.0187(4) Uani 1 1 d . . . . .
H11A H 0.806436 0.402630 0.415181 0.022 Uiso 1 1 calc R U . . .
H11B H 0.933219 0.509261 0.372347 0.022 Uiso 1 1 calc R U . . .
C12 C 0.6938(2) 0.45416(17) 0.30720(9) 0.0143(3) Uani 1 1 d . . . . .
H12 H 0.557639 0.428365 0.318519 0.017 Uiso 1 1 calc R U . . .
C13 C 0.7802(2) 0.35684(16) 0.24887(9) 0.0141(3) Uani 1 1 d . . . . .
C14 C 0.7191(3) 0.21741(18) 0.25210(11) 0.0229(4) Uani 1 1 d . . . . .
H14A H 0.577653 0.212301 0.254442 0.034 Uiso 1 1 calc R U . . .
H14B H 0.776363 0.176719 0.298840 0.034 Uiso 1 1 calc R U . . .
H14C H 0.763531 0.172633 0.205117 0.034 Uiso 1 1 calc R U . . .
C15 C 0.9962(3) 0.38166(19) 0.22866(10) 0.0171(3) Uani 1 1 d . . . . .
H15A H 1.062454 0.441904 0.265211 0.021 Uiso 1 1 calc R U . . .
H15B H 1.072580 0.301725 0.222317 0.021 Uiso 1 1 calc R U . . .
C16 C 0.9336(2) 0.44468(16) 0.14974(9) 0.0125(3) Uani 1 1 d . . . . .
H16 H 0.990661 0.532367 0.142540 0.015 Uiso 1 1 calc R U . . .
C17 C 0.9677(2) 0.35768(16) 0.08123(9) 0.0112(3) Uani 1 1 d . . . . .
C18 C 0.8130(2) 0.34745(16) 0.01844(9) 0.0119(3) Uani 1 1 d . . . . .
H18 H 0.839133 0.267857 -0.012706 0.014 Uiso 1 1 calc R U . . .
C19 C 0.8095(2) 0.46296(17) -0.03905(9) 0.0134(3) Uani 1 1 d . . . . .
C20 C 0.9802(2) 0.4693(2) -0.09383(10) 0.0186(3) Uani 1 1 d . . . . .
H20A H 0.956273 0.535619 -0.133703 0.028 Uiso 1 1 calc R U . . .
H20B H 0.996800 0.385531 -0.119416 0.028 Uiso 1 1 calc R U . . .
H20C H 1.097857 0.490761 -0.063720 0.028 Uiso 1 1 calc R U . . .
C21 C 0.6160(2) 0.43949(18) -0.08193(10) 0.0147(3) Uani 1 1 d . . . . .
H21A H 0.569761 0.519143 -0.108118 0.018 Uiso 1 1 calc R U . . .
H21B H 0.628762 0.370752 -0.121756 0.018 Uiso 1 1 calc R U . . .
C22 C 0.4780(2) 0.39861(16) -0.01795(10) 0.0131(3) Uani 1 1 d . . . . .
H22 H 0.379081 0.336178 -0.038367 0.016 Uiso 1 1 calc R U . . .
C23 C 0.4393(2) 0.53252(16) 0.08983(10) 0.0136(3) Uani 1 1 d . . . . .
C24 C 0.6035(2) 0.33804(15) 0.04887(9) 0.0115(3) Uani 1 1 d . . . . .
H24 H 0.566644 0.245863 0.057008 0.014 Uiso 1 1 calc R U . . .
C25 C 0.5550(2) 0.41887(15) 0.12201(10) 0.0116(3) Uani 1 1 d . . . . .
H25 H 0.461704 0.366006 0.152607 0.014 Uiso 1 1 calc R U . . .
C26 C 0.7226(2) 0.44950(16) 0.17844(9) 0.0109(3) Uani 1 1 d . . . . .
C27 C 0.6912(2) 0.55650(16) 0.24121(9) 0.0129(3) Uani 1 1 d . . . . .
H27A H 0.799261 0.618923 0.245162 0.015 Uiso 1 1 calc R U . . .
H27B H 0.565610 0.601746 0.235327 0.015 Uiso 1 1 calc R U . . .


_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
Si1 C1 1.8765(19) . ?
Si1 C7 1.8576(18) . ?
Si1 C8 1.8646(19) . ?
Si1 C9 1.8736(17) . ?
O1 C17 1.221(2) . ?
O2 H2 0.8400 . ?
O2 C19 1.433(2) . ?
O3 C22 1.451(2) . ?
O3 C23 1.342(2) . ?
O4 C23 1.201(2) . ?
C1 C2 1.398(3) . ?
C1 C6 1.399(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.392(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.374(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(3) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.334(2) . ?
C9 C11 1.514(2) . ?
C10 H10A 0.9500 . ?
C10 H10B 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.521(2) . ?
C12 H12 1.0000 . ?
C12 C13 1.544(2) . ?
C12 C27 1.547(2) . ?
C13 C14 1.508(3) . ?
C13 C15 1.558(2) . ?
C13 C26 1.585(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.552(2) . ?
C16 H16 1.0000 . ?
C16 C17 1.498(2) . ?
C16 C26 1.546(2) . ?
C17 C18 1.505(2) . ?
C18 H18 1.0000 . ?
C18 C19 1.549(2) . ?
C18 C24 1.548(2) . ?
C19 C20 1.518(2) . ?
C19 C21 1.533(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.521(2) . ?
C22 H22 1.0000 . ?
C22 C24 1.554(2) . ?
C23 C25 1.522(2) . ?
C24 H24 1.0000 . ?
C24 C25 1.544(2) . ?
C25 H25 1.0000 . ?
C25 C26 1.527(2) . ?
C26 C27 1.560(2) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?

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
C7 Si1 C1 107.95(9) . . ?
C7 Si1 C8 111.74(9) . . ?
C7 Si1 C9 109.15(8) . . ?
C8 Si1 C1 107.66(9) . . ?
C8 Si1 C9 109.90(9) . . ?
C9 Si1 C1 110.42(8) . . ?
C19 O2 H2 109.5 . . ?
C23 O3 C22 112.53(13) . . ?
C2 C1 Si1 122.14(14) . . ?
C2 C1 C6 116.87(18) . . ?
C6 C1 Si1 120.95(16) . . ?
C1 C2 H2A 119.3 . . ?
C3 C2 C1 121.5(2) . . ?
C3 C2 H2A 119.3 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 H6 119.2 . . ?
C5 C6 C1 121.6(2) . . ?
C5 C6 H6 119.2 . . ?
Si1 C7 H7A 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
Si1 C8 H8A 109.5 . . ?
Si1 C8 H8B 109.5 . . ?
Si1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 Si1 119.42(13) . . ?
C10 C9 C11 122.28(16) . . ?
C11 C9 Si1 118.29(12) . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
C9 C11 H11A 108.3 . . ?
C9 C11 H11B 108.3 . . ?
C9 C11 C12 116.09(15) . . ?
H11A C11 H11B 107.4 . . ?
C12 C11 H11A 108.3 . . ?
C12 C11 H11B 108.3 . . ?
C11 C12 H12 108.9 . . ?
C11 C12 C13 120.12(14) . . ?
C11 C12 C27 119.48(15) . . ?
C13 C12 H12 108.9 . . ?
C13 C12 C27 88.87(12) . . ?
C27 C12 H12 108.9 . . ?
C12 C13 C15 114.57(14) . . ?
C12 C13 C26 89.81(12) . . ?
C14 C13 C12 119.49(14) . . ?
C14 C13 C15 115.87(15) . . ?
C14 C13 C26 122.86(15) . . ?
C15 C13 C26 87.81(12) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 113.6 . . ?
C13 C15 H15B 113.6 . . ?
H15A C15 H15B 110.8 . . ?
C16 C15 C13 90.41(12) . . ?
C16 C15 H15A 113.6 . . ?
C16 C15 H15B 113.6 . . ?
C15 C16 H16 112.6 . . ?
C17 C16 C15 112.18(14) . . ?
C17 C16 H16 112.6 . . ?
C17 C16 C26 115.32(13) . . ?
C26 C16 C15 89.42(12) . . ?
C26 C16 H16 112.6 . . ?
O1 C17 C16 120.27(15) . . ?
O1 C17 C18 121.13(15) . . ?
C16 C17 C18 118.59(14) . . ?
C17 C18 H18 107.7 . . ?
C17 C18 C19 113.56(13) . . ?
C17 C18 C24 115.02(13) . . ?
C19 C18 H18 107.7 . . ?
C24 C18 H18 107.7 . . ?
C24 C18 C19 104.83(13) . . ?
O2 C19 C18 105.62(13) . . ?
O2 C19 C20 111.44(14) . . ?
O2 C19 C21 110.55(13) . . ?
C20 C19 C18 114.76(14) . . ?
C20 C19 C21 113.17(14) . . ?
C21 C19 C18 100.60(13) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 110.8 . . ?
C19 C21 H21B 110.8 . . ?
H21A C21 H21B 108.9 . . ?
C22 C21 C19 104.71(13) . . ?
C22 C21 H21A 110.8 . . ?
C22 C21 H21B 110.8 . . ?
O3 C22 C21 109.16(14) . . ?
O3 C22 H22 111.3 . . ?
O3 C22 C24 106.65(12) . . ?
C21 C22 H22 111.3 . . ?
C21 C22 C24 106.87(13) . . ?
C24 C22 H22 111.3 . . ?
O3 C23 C25 110.75(14) . . ?
O4 C23 O3 120.29(16) . . ?
O4 C23 C25 128.72(16) . . ?
C18 C24 C22 104.01(13) . . ?
C18 C24 H24 110.4 . . ?
C22 C24 H24 110.4 . . ?
C25 C24 C18 116.90(13) . . ?
C25 C24 C22 104.31(13) . . ?
C25 C24 H24 110.4 . . ?
C23 C25 C24 104.41(13) . . ?
C23 C25 H25 105.9 . . ?
C23 C25 C26 117.04(13) . . ?
C24 C25 H25 105.9 . . ?
C26 C25 C24 116.77(13) . . ?
C26 C25 H25 105.9 . . ?
C16 C26 C13 89.64(12) . . ?
C16 C26 C27 112.50(13) . . ?
C25 C26 C13 122.03(14) . . ?
C25 C26 C16 120.17(13) . . ?
C25 C26 C27 117.93(13) . . ?
C27 C26 C13 86.99(12) . . ?
C12 C27 C26 90.61(12) . . ?
C12 C27 H27A 113.5 . . ?
C12 C27 H27B 113.5 . . ?
C26 C27 H27A 113.5 . . ?
C26 C27 H27B 113.5 . . ?
H27A C27 H27B 110.8 . . ?

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
_geom_hbond_publ_flag
O2 H2 O1 0.84 1.95 2.7880(18) 173.8 2_755 yes

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
Si1 C1 C2 C3 178.21(15) . . . . ?
Si1 C1 C6 C5 -177.84(16) . . . . ?
Si1 C9 C11 C12 -175.06(13) . . . . ?
O1 C17 C18 C19 -101.67(18) . . . . ?
O1 C17 C18 C24 137.55(16) . . . . ?
O2 C19 C21 C22 -69.88(17) . . . . ?
O3 C22 C24 C18 -116.84(13) . . . . ?
O3 C22 C24 C25 6.18(16) . . . . ?
O3 C23 C25 C24 11.88(17) . . . . ?
O3 C23 C25 C26 142.66(14) . . . . ?
O4 C23 C25 C24 -173.87(17) . . . . ?
O4 C23 C25 C26 -43.1(2) . . . . ?
C1 Si1 C9 C10 108.36(16) . . . . ?
C1 Si1 C9 C11 -72.16(15) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
C7 Si1 C1 C2 -2.71(18) . . . . ?
C7 Si1 C1 C6 174.94(15) . . . . ?
C7 Si1 C9 C10 -133.12(15) . . . . ?
C7 Si1 C9 C11 46.36(16) . . . . ?
C8 Si1 C1 C2 -123.49(16) . . . . ?
C8 Si1 C1 C6 54.16(17) . . . . ?
C8 Si1 C9 C10 -10.26(18) . . . . ?
C8 Si1 C9 C11 169.22(14) . . . . ?
C9 Si1 C1 C2 116.53(15) . . . . ?
C9 Si1 C1 C6 -65.82(17) . . . . ?
C9 C11 C12 C13 175.87(15) . . . . ?
C9 C11 C12 C27 68.3(2) . . . . ?
C10 C9 C11 C12 4.4(3) . . . . ?
C11 C12 C13 C14 93.2(2) . . . . ?
C11 C12 C13 C15 -50.9(2) . . . . ?
C11 C12 C13 C26 -138.41(16) . . . . ?
C11 C12 C27 C26 139.19(15) . . . . ?
C12 C13 C15 C16 -101.10(15) . . . . ?
C12 C13 C26 C16 126.97(12) . . . . ?
C12 C13 C26 C25 -106.95(16) . . . . ?
C12 C13 C26 C27 14.41(12) . . . . ?
C13 C12 C27 C26 14.75(12) . . . . ?
C13 C15 C16 C17 -104.61(14) . . . . ?
C13 C15 C16 C26 12.62(13) . . . . ?
C13 C26 C27 C12 -14.38(12) . . . . ?
C14 C13 C15 C16 113.47(16) . . . . ?
C14 C13 C26 C16 -107.31(17) . . . . ?
C14 C13 C26 C25 18.8(2) . . . . ?
C14 C13 C26 C27 140.14(16) . . . . ?
C15 C13 C26 C16 12.37(12) . . . . ?
C15 C13 C26 C25 138.45(15) . . . . ?
C15 C13 C26 C27 -100.19(12) . . . . ?
C15 C16 C17 O1 -43.4(2) . . . . ?
C15 C16 C17 C18 136.71(15) . . . . ?
C15 C16 C26 C13 -12.41(13) . . . . ?
C15 C16 C26 C25 -139.99(15) . . . . ?
C15 C16 C26 C27 74.19(15) . . . . ?
C16 C17 C18 C19 78.18(18) . . . . ?
C16 C17 C18 C24 -42.6(2) . . . . ?
C16 C26 C27 C12 -102.75(14) . . . . ?
C17 C16 C26 C13 101.98(15) . . . . ?
C17 C16 C26 C25 -25.6(2) . . . . ?
C17 C16 C26 C27 -171.42(13) . . . . ?
C17 C18 C19 O2 -53.01(17) . . . . ?
C17 C18 C19 C20 70.15(18) . . . . ?
C17 C18 C19 C21 -168.04(13) . . . . ?
C17 C18 C24 C22 151.53(14) . . . . ?
C17 C18 C24 C25 37.2(2) . . . . ?
C18 C19 C21 C22 41.39(16) . . . . ?
C18 C24 C25 C23 103.80(15) . . . . ?
C18 C24 C25 C26 -27.1(2) . . . . ?
C19 C18 C24 C22 26.08(16) . . . . ?
C19 C18 C24 C25 -88.27(16) . . . . ?
C19 C21 C22 O3 88.93(15) . . . . ?
C19 C21 C22 C24 -26.05(17) . . . . ?
C20 C19 C21 C22 164.31(15) . . . . ?
C21 C22 C24 C18 -0.18(17) . . . . ?
C21 C22 C24 C25 122.84(14) . . . . ?
C22 O3 C23 O4 176.83(15) . . . . ?
C22 O3 C23 C25 -8.36(18) . . . . ?
C22 C24 C25 C23 -10.38(15) . . . . ?
C22 C24 C25 C26 -141.32(14) . . . . ?
C23 O3 C22 C21 -113.97(15) . . . . ?
C23 O3 C22 C24 1.16(17) . . . . ?
C23 C25 C26 C13 146.06(15) . . . . ?
C23 C25 C26 C16 -103.13(17) . . . . ?
C23 C25 C26 C27 40.9(2) . . . . ?
C24 C18 C19 O2 73.35(14) . . . . ?
C24 C18 C19 C20 -163.50(14) . . . . ?
C24 C18 C19 C21 -41.68(15) . . . . ?
C24 C25 C26 C13 -89.16(18) . . . . ?
C24 C25 C26 C16 21.6(2) . . . . ?
C24 C25 C26 C27 165.67(13) . . . . ?
C25 C26 C27 C12 110.60(15) . . . . ?
C26 C13 C15 C16 -12.32(12) . . . . ?
C26 C16 C17 O1 -143.85(16) . . . . ?
C26 C16 C17 C18 36.3(2) . . . . ?
C27 C12 C13 C14 -142.94(16) . . . . ?
C27 C12 C13 C15 72.99(15) . . . . ?
C27 C12 C13 C26 -14.51(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
