# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_15a
_database_code_depnum_ccdc_archive 'CCDC 1410262'
_audit_update_record             
;
2015-10-15 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;
_audit_creation_date             2015-06-30
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)

Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.
;
_chemical_name_systematic        
'(1S,2R,7S,8aS)-1,2,7-trihydroxy-5,5-dimethyloctahydro-1H-indolizin-4-ium chloride'
_chemical_formula_moiety         'C10 H20 N O3, Cl'
_chemical_formula_sum            'C10 H20 Cl N O3'
_chemical_formula_weight         237.72
_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'
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      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                   6.82581(5)
_cell_length_b                   12.02340(7)
_cell_length_c                   14.64680(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1202.054(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    26693
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      67.0640
_cell_measurement_theta_min      4.7140
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.741
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
'CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm.'
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0103
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33361
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.750
_diffrn_reflns_theta_max         67.168
_diffrn_reflns_theta_min         4.758
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   12.00  115.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       41.1363   57.0000   60.0000 103

#__ type_ start__ end____ width___ exp.time_
  2 omega    7.00  120.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       41.1363   77.0000 -180.0000 113

#__ type_ start__ end____ width___ exp.time_
  3 omega   48.00  121.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       41.1363  161.0000  152.0000 73

#__ type_ start__ end____ width___ exp.time_
  4 omega   -5.00  123.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       41.1363   19.0000    0.0000 128

#__ type_ start__ end____ width___ exp.time_
  5 omega  -10.00   92.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       41.1363 -117.0000  -85.0000 102

#__ type_ start__ end____ width___ exp.time_
  6 omega   12.00  115.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       41.1363   57.0000  120.0000 103

#__ type_ start__ end____ width___ exp.time_
  7 omega   16.00  129.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   77.0000  -11.3822 113

#__ type_ start__ end____ width___ exp.time_
  8 omega   16.00  129.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   77.0000  -70.7882 113

#__ type_ start__ end____ width___ exp.time_
  9 omega   20.00  133.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000 -147.0319 113

#__ type_ start__ end____ width___ exp.time_
 10 omega   20.00  133.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000   22.5443 113

#__ type_ start__ end____ width___ exp.time_
 11 omega   20.00  134.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000   51.4205 114

#__ type_ start__ end____ width___ exp.time_
 12 omega   24.00  138.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   79.0000   63.5892 114

#__ type_ start__ end____ width___ exp.time_
 13 omega   24.00  138.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   79.0000 -178.7908 114

#__ type_ start__ end____ width___ exp.time_
 14 omega   28.00  142.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   79.0000  100.6025 114

#__ type_ start__ end____ width___ exp.time_
 15 omega   32.00  145.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   78.0000   73.3947 113

#__ type_ start__ end____ width___ exp.time_
 16 omega   32.00  146.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   79.0000  133.3587 114

#__ type_ start__ end____ width___ exp.time_
 17 omega   34.00   60.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000  164.4682 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   36.00   61.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   79.0000  -83.3355 25

#__ type_ start__ end____ width___ exp.time_
 19 omega   36.00   62.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   78.0000  -48.1603 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   41.00   67.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   78.0000 -107.2474 26

#__ type_ start__ end____ width___ exp.time_
 21 omega   41.00   72.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   79.0000  -23.2225 31

#__ type_ start__ end____ width___ exp.time_
 22 omega  -85.00  -53.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -62.0000  -18.4345 32

#__ type_ start__ end____ width___ exp.time_
 23 omega  -81.00  -53.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -76.0000   24.7890 28

#__ type_ start__ end____ width___ exp.time_
 24 omega  -76.00  -50.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega  -80.00  -50.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -76.0000   36.1809 30

#__ type_ start__ end____ width___ exp.time_
 26 omega  -75.00  -49.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 27 omega  -75.00  -49.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  168.8117 26

#__ type_ start__ end____ width___ exp.time_
 28 omega  -78.00  -51.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -73.0000 -171.7670 27

#__ type_ start__ end____ width___ exp.time_
 29 omega  -76.00  -50.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 30 omega  -75.00  -49.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 31 omega  -77.00  -51.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -73.0000   64.2323 26

#__ type_ start__ end____ width___ exp.time_
 32 omega  -77.00  -51.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 33 omega  -91.00  -49.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  150.0000 42

#__ type_ start__ end____ width___ exp.time_
 34 omega  -85.00  -49.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  120.0000 36

#__ type_ start__ end____ width___ exp.time_
 35 omega  -76.00  -50.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 36 omega  -77.00  -51.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 37 omega   60.00   94.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -90.0000 34

#__ type_ start__ end____ width___ exp.time_
 38 omega   85.00  135.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000    0.0000 50

#__ type_ start__ end____ width___ exp.time_
 39 omega   60.00   97.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -30.0000 37

#__ type_ start__ end____ width___ exp.time_
 40 omega   60.00  147.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -120.0000 87

#__ type_ start__ end____ width___ exp.time_
 41 omega   21.00   46.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 42 omega  123.00  160.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000 -150.0000 37

#__ type_ start__ end____ width___ exp.time_
 43 omega   86.00  120.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -67.0000 -121.6956 34

#__ type_ start__ end____ width___ exp.time_
 44 omega   33.00   65.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000   60.0000 32

#__ type_ start__ end____ width___ exp.time_
 45 omega   33.00   59.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -67.0000 -121.6956 26

#__ type_ start__ end____ width___ exp.time_
 46 omega  131.00  157.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 47 omega   80.00  123.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000 -113.2332 43

#__ type_ start__ end____ width___ exp.time_
 48 omega   91.00  119.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000 -150.0000 28

#__ type_ start__ end____ width___ exp.time_
 49 omega   78.00  127.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000  150.0000 49

#__ type_ start__ end____ width___ exp.time_
 50 omega   97.00  171.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   30.0000 74

#__ type_ start__ end____ width___ exp.time_
 51 omega   62.00  123.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000 -180.0000 61

#__ type_ start__ end____ width___ exp.time_
 52 omega    9.00   50.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000 -113.2332 41

#__ type_ start__ end____ width___ exp.time_
 53 omega   64.00   93.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   30.0000 29

#__ type_ start__ end____ width___ exp.time_
 54 omega   12.00  133.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000   23.7007 121

#__ type_ start__ end____ width___ exp.time_
 55 omega   27.00   52.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 56 omega   87.00  121.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000  -30.0000 34

#__ type_ start__ end____ width___ exp.time_
 57 omega   93.00  145.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  120.0000 52

#__ type_ start__ end____ width___ exp.time_
 58 omega   60.00   89.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  120.0000 29

#__ type_ start__ end____ width___ exp.time_
 59 omega   61.00  109.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000 -177.1363 48

#__ type_ start__ end____ width___ exp.time_
 60 omega   25.00   76.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000   90.0000 51

#__ type_ start__ end____ width___ exp.time_
 61 omega  129.00  164.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000  -30.0000 35

#__ type_ start__ end____ width___ exp.time_
 62 omega   29.00   58.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000 -177.1363 29

#__ type_ start__ end____ width___ exp.time_
 63 omega   88.00  147.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -15.0000  150.0000 59

#__ type_ start__ end____ width___ exp.time_
 64 omega   18.00   47.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -15.0000  150.0000 29

#__ type_ start__ end____ width___ exp.time_
 65 omega   74.00  109.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000  -30.0000 35

#__ type_ start__ end____ width___ exp.time_
 66 omega   61.00  171.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   60.0000 110

#__ type_ start__ end____ width___ exp.time_
 67 omega   63.00  143.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -60.0000 80

#__ type_ start__ end____ width___ exp.time_
 68 omega   21.00   80.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000  120.0000 59

#__ type_ start__ end____ width___ exp.time_
 69 omega   62.00  144.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  150.0000 82

#__ type_ start__ end____ width___ exp.time_
 70 omega   61.00  124.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -150.0000 63

#__ type_ start__ end____ width___ exp.time_
 71 omega  147.00  172.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 72 omega   60.00  100.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000    0.0000 40

#__ type_ start__ end____ width___ exp.time_
 73 omega  139.00  171.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000  -30.0000 32

#__ type_ start__ end____ width___ exp.time_
 74 omega   63.00  123.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   90.0000 60

#__ type_ start__ end____ width___ exp.time_
 75 omega   87.00  113.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 76 omega  108.00  154.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000  -90.0000 46

#__ type_ start__ end____ width___ exp.time_
 77 omega  114.00  140.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 78 omega  139.00  172.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
 79 omega   63.00   97.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -180.0000 34

#__ type_ start__ end____ width___ exp.time_
 80 omega  137.00  163.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -90.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0019839000
_diffrn_orient_matrix_UB_12      0.0867686000
_diffrn_orient_matrix_UB_13      -0.0773765000
_diffrn_orient_matrix_UB_21      -0.0490001000
_diffrn_orient_matrix_UB_22      0.0918345000
_diffrn_orient_matrix_UB_23      0.0696515000
_diffrn_orient_matrix_UB_31      0.2203567000
_diffrn_orient_matrix_UB_32      0.0212259000
_diffrn_orient_matrix_UB_33      0.0149198000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2128
_reflns_number_total             2148
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 868 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(3)
_refine_ls_extinction_coef       0.0022(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0220
_refine_ls_R_factor_gt           0.0217
_refine_ls_restrained_S_all      1.034
_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)+(0.0360P)²+0.3460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0578
_refine_ls_wR_factor_ref         0.0580
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1b), C2(H2a), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3a,H3b), C6(H6a,H6b), C8(H8a,H8b)
2.c Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c)
;
_atom_sites_solution_hydrogens   mixed
_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 0.5780(2) 0.78723(11) 0.33696(10) 0.0193(3) Uani 1 1 d . . . . .
H1 H 0.475(4) 0.814(2) 0.3437(18) 0.026(7) Uiso 1 1 d . . . . .
O2 O 0.2096(2) 0.68811(12) 0.30191(11) 0.0230(3) Uani 1 1 d . . . . .
H2 H 0.199(4) 0.735(2) 0.2649(18) 0.028 Uiso 1 1 d R . . . .
O3 O 0.7811(2) 0.55109(11) 0.64496(10) 0.0192(3) Uani 1 1 d . . . . .
H3 H 0.739(4) 0.5575(18) 0.6976(19) 0.018(6) Uiso 1 1 d . . . . .
N1 N 0.4703(2) 0.50277(12) 0.40529(10) 0.0111(3) Uani 1 1 d . . . . .
H1A H 0.583(3) 0.4711(17) 0.3912(14) 0.009(5) Uiso 1 1 d . . . . .
C1 C 0.5565(3) 0.67088(14) 0.33608(14) 0.0156(4) Uani 1 1 d . . . . .
H1B H 0.6792 0.6371 0.3111 0.019 Uiso 1 1 calc R . . . .
C2 C 0.3807(3) 0.62623(16) 0.28128(12) 0.0171(4) Uani 1 1 d . . . . .
H2A H 0.4084 0.6262 0.2142 0.021 Uiso 1 1 calc R . . . .
C3 C 0.3517(3) 0.50765(14) 0.31761(11) 0.0150(4) Uani 1 1 d . . . . .
H3A H 0.2114 0.4930 0.3299 0.018 Uiso 1 1 calc R . . . .
H3B H 0.4000 0.4522 0.2730 0.018 Uiso 1 1 calc R . . . .
C5 C 0.3909(3) 0.43423(15) 0.48507(12) 0.0139(4) Uani 1 1 d . . . . .
C6 C 0.5526(3) 0.44008(15) 0.55845(12) 0.0157(4) Uani 1 1 d . . . . .
H6A H 0.5055 0.4013 0.6139 0.019 Uiso 1 1 calc R . . . .
H6B H 0.6688 0.3993 0.5358 0.019 Uiso 1 1 calc R . . . .
C7 C 0.6157(3) 0.55747(16) 0.58507(12) 0.0162(4) Uani 1 1 d . . . . .
H7 H 0.506(3) 0.5968(18) 0.6161(16) 0.019 Uiso 1 1 d R . . . .
C8 C 0.6768(3) 0.62384(15) 0.50103(13) 0.0164(4) Uani 1 1 d . . . . .
H8A H 0.7035 0.7019 0.5187 0.020 Uiso 1 1 calc R . . . .
H8B H 0.7985 0.5920 0.4752 0.020 Uiso 1 1 calc R . . . .
C9 C 0.5166(3) 0.62082(15) 0.43008(12) 0.0134(4) Uani 1 1 d . . . . .
H9 H 0.3963 0.6562 0.4561 0.016 Uiso 1 1 calc R . . . .
C10 C 0.1965(3) 0.48040(17) 0.51860(13) 0.0195(4) Uani 1 1 d . . . . .
H10A H 0.2171 0.5544 0.5449 0.029 Uiso 1 1 calc GR . . . .
H10B H 0.1421 0.4307 0.5652 0.029 Uiso 1 1 calc GR . . . .
H10C H 0.1049 0.4858 0.4673 0.029 Uiso 1 1 calc GR . . . .
C11 C 0.3662(3) 0.31519(15) 0.45075(14) 0.0188(4) Uani 1 1 d . . . . .
H11A H 0.3414 0.2657 0.5026 0.028 Uiso 1 1 calc GR . . . .
H11B H 0.4860 0.2917 0.4193 0.028 Uiso 1 1 calc GR . . . .
H11C H 0.2554 0.3118 0.4083 0.028 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.84860(6) 0.38349(4) 0.33796(3) 0.01734(14) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.78(3) . ?
O1 C1 1.407(2) . ?
O2 H2 0.78(3) . ?
O2 C2 1.417(2) . ?
O3 H3 0.83(3) . ?
O3 C7 1.432(2) . ?
N1 H1A 0.89(2) . ?
N1 C3 1.519(2) . ?
N1 C5 1.529(2) . ?
N1 C9 1.499(2) . ?
C1 H1B 1.0000 . ?
C1 C2 1.540(3) . ?
C1 C9 1.527(3) . ?
C2 H2A 1.0000 . ?
C2 C3 1.535(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 C6 1.542(3) . ?
C5 C10 1.520(3) . ?
C5 C11 1.526(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.526(3) . ?
C7 H7 1.00(2) . ?
C7 C8 1.525(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.509(2) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 108.8(19) . . ?
C2 O2 H2 108(2) . . ?
C7 O3 H3 107.1(18) . . ?
C3 N1 H1A 106.5(14) . . ?
C3 N1 C5 118.56(14) . . ?
C5 N1 H1A 104.8(13) . . ?
C9 N1 H1A 106.3(14) . . ?
C9 N1 C3 106.29(13) . . ?
C9 N1 C5 113.58(13) . . ?
O1 C1 H1B 108.7 . . ?
O1 C1 C2 115.62(15) . . ?
O1 C1 C9 113.72(16) . . ?
C2 C1 H1B 108.7 . . ?
C9 C1 H1B 108.7 . . ?
C9 C1 C2 101.14(14) . . ?
O2 C2 C1 110.37(15) . . ?
O2 C2 H2A 111.4 . . ?
O2 C2 C3 107.89(16) . . ?
C1 C2 H2A 111.4 . . ?
C3 C2 C1 104.11(14) . . ?
C3 C2 H2A 111.4 . . ?
N1 C3 C2 105.08(14) . . ?
N1 C3 H3A 110.7 . . ?
N1 C3 H3B 110.7 . . ?
C2 C3 H3A 110.7 . . ?
C2 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
N1 C5 C6 104.73(14) . . ?
C10 C5 N1 111.07(15) . . ?
C10 C5 C6 112.52(15) . . ?
C10 C5 C11 110.65(16) . . ?
C11 C5 N1 107.03(14) . . ?
C11 C5 C6 110.56(15) . . ?
C5 C6 H6A 108.5 . . ?
C5 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
C7 C6 C5 114.97(15) . . ?
C7 C6 H6A 108.5 . . ?
C7 C6 H6B 108.5 . . ?
O3 C7 C6 109.23(15) . . ?
O3 C7 H7 109.9(13) . . ?
O3 C7 C8 107.87(15) . . ?
C6 C7 H7 110.1(13) . . ?
C8 C7 C6 110.79(15) . . ?
C8 C7 H7 109.0(13) . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C9 C8 C7 110.19(15) . . ?
C9 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
N1 C9 C1 101.10(13) . . ?
N1 C9 C8 110.02(14) . . ?
N1 C9 H9 108.8 . . ?
C1 C9 H9 108.8 . . ?
C8 C9 C1 118.81(16) . . ?
C8 C9 H9 108.8 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
O1 H1 O3 0.78(3) 2.10(3) 2.821(2) 154(3) 4_466
O2 H2 Cl1 0.78(3) 2.36(3) 3.1421(15) 176(3) 3_655
O3 H3 Cl1 0.83(3) 2.26(3) 3.0647(15) 166(2) 2_665
N1 H1A Cl1 0.89(2) 2.23(2) 3.1142(16) 172.1(19) .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 O2 -45.8(2) . . . . ?
O1 C1 C2 C3 -161.40(16) . . . . ?
O1 C1 C9 N1 171.51(15) . . . . ?
O1 C1 C9 C8 -68.1(2) . . . . ?
O2 C2 C3 N1 -102.52(16) . . . . ?
O3 C7 C8 C9 172.76(14) . . . . ?
N1 C5 C6 C7 54.39(19) . . . . ?
C1 C2 C3 N1 14.75(18) . . . . ?
C2 C1 C9 N1 46.91(16) . . . . ?
C2 C1 C9 C8 167.32(16) . . . . ?
C3 N1 C5 C6 175.75(14) . . . . ?
C3 N1 C5 C10 -62.54(19) . . . . ?
C3 N1 C5 C11 58.3(2) . . . . ?
C3 N1 C9 C1 -38.60(17) . . . . ?
C3 N1 C9 C8 -165.05(14) . . . . ?
C5 N1 C3 C2 144.11(15) . . . . ?
C5 N1 C9 C1 -170.74(15) . . . . ?
C5 N1 C9 C8 62.81(19) . . . . ?
C5 C6 C7 O3 -173.15(15) . . . . ?
C5 C6 C7 C8 -54.5(2) . . . . ?
C6 C7 C8 C9 53.2(2) . . . . ?
C7 C8 C9 N1 -57.34(19) . . . . ?
C7 C8 C9 C1 -173.08(15) . . . . ?
C9 N1 C3 C2 14.80(18) . . . . ?
C9 N1 C5 C6 -58.38(18) . . . . ?
C9 N1 C5 C10 63.33(19) . . . . ?
C9 N1 C5 C11 -175.79(15) . . . . ?
C9 C1 C2 O2 77.45(17) . . . . ?
C9 C1 C2 C3 -38.09(17) . . . . ?
C10 C5 C6 C7 -66.4(2) . . . . ?
C11 C5 C6 C7 169.35(16) . . . . ?



####################################################################### 
# 
# 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_13
_database_code_depnum_ccdc_archive 'CCDC 1410265'
_audit_update_record             
;
2015-10-15 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;
_audit_creation_date             2015-06-30
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)

Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.
;
_chemical_name_systematic        
(R)-2-((tert-butyldimethylsilyl)oxy)-1-((4R,5S)-5-((4S,6S)-2',2'-dimethyl-7-oxa-1-azaspiro[bicyclo[2.2.1]heptane-2,5'-[1,3]dioxan]-6-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol
_chemical_formula_moiety         'C23 H43 N O7 Si'
_chemical_formula_sum            'C23 H43 N O7 Si'
_chemical_formula_weight         473.67
_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'
Si Si 0.2541 0.3302 '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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.96665(7)
_cell_length_b                   10.06647(10)
_cell_length_c                   31.8330(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2552.88(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15581
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.6690
_cell_measurement_theta_min      4.5880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.154
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            22949
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.680
_diffrn_reflns_theta_max         66.680
_diffrn_reflns_theta_min         4.607
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 10.3347
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   23.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0321   38.0000   30.0000 60

#__ type_ start__ end____ width___ exp.time_
  2 omega    7.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0321   77.0000   90.0000 108

#__ type_ start__ end____ width___ exp.time_
  3 omega   16.00   42.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -30.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   66.00   92.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   61.00   89.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000  150.0000 28

#__ type_ start__ end____ width___ exp.time_
  6 omega   20.00   77.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000  -60.0000 57

#__ type_ start__ end____ width___ exp.time_
  7 omega   64.00   94.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000   90.0000 30

#__ type_ start__ end____ width___ exp.time_
  8 omega   19.00   44.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega  123.00  163.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  134.0000   41.0000 40

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00   64.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -77.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   70.00   97.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -77.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 12 omega   60.00   97.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000   90.0000 37

#__ type_ start__ end____ width___ exp.time_
 13 omega  123.00  149.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   20.00   57.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -30.0000  -30.0000 37

#__ type_ start__ end____ width___ exp.time_
 15 omega   71.00   96.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 16 omega   63.00  142.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000  120.0000 79

#__ type_ start__ end____ width___ exp.time_
 17 omega   21.00   55.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000   30.0000 34

#__ type_ start__ end____ width___ exp.time_
 18 omega   75.00  157.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  125.0000   60.0000 82

#__ type_ start__ end____ width___ exp.time_
 19 omega   46.00   72.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   14.00   62.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -95.0000  -90.0000 48

#__ type_ start__ end____ width___ exp.time_
 21 omega   88.00  114.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   45.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 22 omega   63.00  110.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -88.0000   35.5318 47

#__ type_ start__ end____ width___ exp.time_
 23 omega  -71.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0321   57.0000 -150.0000 104

#__ type_ start__ end____ width___ exp.time_
 24 omega -104.00  -24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0321  135.0000 -138.0000 80

#__ type_ start__ end____ width___ exp.time_
 25 omega   15.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0321   38.0000 -150.0000 102

#__ type_ start__ end____ width___ exp.time_
 26 omega   11.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0321   57.0000  -90.0000 104

#__ type_ start__ end____ width___ exp.time_
 27 omega   62.00   90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000 -120.0000 28

#__ type_ start__ end____ width___ exp.time_
 28 omega   43.00  174.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   18.0000    1.0000 131
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0066349000
_diffrn_orient_matrix_UB_12      -0.0220117000
_diffrn_orient_matrix_UB_13      -0.0478634000
_diffrn_orient_matrix_UB_21      -0.0450238000
_diffrn_orient_matrix_UB_22      -0.1471227000
_diffrn_orient_matrix_UB_23      0.0071465000
_diffrn_orient_matrix_UB_31      -0.1879387000
_diffrn_orient_matrix_UB_32      0.0359705000
_diffrn_orient_matrix_UB_33      -0.0000331000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4423
_reflns_number_total             4512
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 1844 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(10)
_refine_ls_extinction_coef       0.00102(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4512
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0278
_refine_ls_restrained_S_all      1.041
_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)+(0.0416P)²+0.5848P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0713
_refine_ls_wR_factor_ref         0.0720
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2), C10(H10), C14(H14), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C16(H16A,H16B), C17(H17A,H17B), C19(H19A,H19B), C20(H20A,H20B)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,
 H9B,H9C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C22(H22A,H22B,H22C),
 C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.89512(7) 0.35420(5) 0.39218(2) 0.01629(14) Uani 1 1 d . . . . .
O1 O 0.6240(2) 0.61500(15) 0.33743(4) 0.0201(3) Uani 1 1 d . . . . .
H1 H 0.550(4) 0.664(3) 0.3283(8) 0.027(7) Uiso 1 1 d . . . . .
O2 O 0.18986(18) 0.79439(14) 0.32676(4) 0.0180(3) Uani 1 1 d . . . . .
O3 O 0.82799(18) 0.50126(14) 0.40670(4) 0.0187(3) Uani 1 1 d . . . . .
O4 O 0.61574(18) 0.74882(14) 0.44412(4) 0.0161(3) Uani 1 1 d . . . . .
O5 O 0.33001(17) 0.75120(16) 0.44529(4) 0.0190(3) Uani 1 1 d . . . . .
O6 O 0.68878(19) 0.95358(14) 0.30285(4) 0.0183(3) Uani 1 1 d . . . . .
O7 O 0.55057(18) 0.82489(15) 0.25207(4) 0.0186(3) Uani 1 1 d . . . . .
N1 N 0.3693(2) 0.82218(16) 0.33185(5) 0.0148(4) Uani 1 1 d . . . . .
C1 C 0.6849(3) 0.6850(2) 0.37339(6) 0.0162(4) Uani 1 1 d . . . . .
H1A H 0.7006 0.7808 0.3661 0.019 Uiso 1 1 calc R . . . .
C2 C 0.1271(3) 0.9228(2) 0.34106(6) 0.0195(4) Uani 1 1 d . . . . .
H2 H 0.0020 0.9307 0.3406 0.023 Uiso 1 1 calc R . . . .
C3 C 0.8520(3) 0.6259(2) 0.38657(6) 0.0184(4) Uani 1 1 d . . . . .
H3A H 0.9241 0.6139 0.3615 0.022 Uiso 1 1 calc R . . . .
H3B H 0.9097 0.6875 0.4060 0.022 Uiso 1 1 calc R . . . .
C4 C 0.7709(3) 0.2342(2) 0.42551(7) 0.0189(4) Uani 1 1 d . . . . .
C5 C 0.5818(3) 0.2562(2) 0.41821(7) 0.0242(5) Uani 1 1 d . . . . .
H5A H 0.5504 0.3452 0.4279 0.036 Uiso 1 1 calc GR . . . .
H5B H 0.5178 0.1894 0.4339 0.036 Uiso 1 1 calc GR . . . .
H5C H 0.5568 0.2480 0.3882 0.036 Uiso 1 1 calc GR . . . .
C6 C 0.8156(3) 0.0910(2) 0.41348(7) 0.0242(5) Uani 1 1 d . . . . .
H6A H 0.7985 0.0786 0.3832 0.036 Uiso 1 1 calc GR . . . .
H6B H 0.7435 0.0294 0.4290 0.036 Uiso 1 1 calc GR . . . .
H6C H 0.9333 0.0736 0.4205 0.036 Uiso 1 1 calc GR . . . .
C7 C 0.8085(3) 0.2553(3) 0.47238(7) 0.0301(5) Uani 1 1 d . . . . .
H7A H 0.9284 0.2410 0.4776 0.045 Uiso 1 1 calc GR . . . .
H7B H 0.7429 0.1922 0.4891 0.045 Uiso 1 1 calc GR . . . .
H7C H 0.7782 0.3462 0.4804 0.045 Uiso 1 1 calc GR . . . .
C8 C 1.1258(3) 0.3434(2) 0.40224(8) 0.0289(5) Uani 1 1 d . . . . .
H8A H 1.1847 0.4082 0.3846 0.043 Uiso 1 1 calc GR . . . .
H8B H 1.1655 0.2538 0.3955 0.043 Uiso 1 1 calc GR . . . .
H8C H 1.1483 0.3627 0.4319 0.043 Uiso 1 1 calc GR . . . .
C9 C 0.8529(3) 0.3260(2) 0.33524(7) 0.0283(5) Uani 1 1 d . . . . .
H9A H 0.7323 0.3346 0.3298 0.042 Uiso 1 1 calc GR . . . .
H9B H 0.8902 0.2366 0.3274 0.042 Uiso 1 1 calc GR . . . .
H9C H 0.9142 0.3919 0.3186 0.042 Uiso 1 1 calc GR . . . .
C10 C 0.5581(2) 0.6729(2) 0.40877(6) 0.0149(4) Uani 1 1 d . . . . .
H10 H 0.5493 0.5775 0.4172 0.018 Uiso 1 1 calc R . . . .
C11 C 0.4765(3) 0.7557(2) 0.47197(6) 0.0171(4) Uani 1 1 d . . . . .
C12 C 0.4727(3) 0.6371(2) 0.50149(7) 0.0207(5) Uani 1 1 d . . . . .
H12A H 0.3725 0.6421 0.5193 0.031 Uiso 1 1 calc GR . . . .
H12B H 0.5733 0.6379 0.5192 0.031 Uiso 1 1 calc GR . . . .
H12C H 0.4699 0.5549 0.4850 0.031 Uiso 1 1 calc GR . . . .
C13 C 0.4817(3) 0.8863(2) 0.49522(7) 0.0230(5) Uani 1 1 d . . . . .
H13A H 0.4803 0.9597 0.4750 0.035 Uiso 1 1 calc GR . . . .
H13B H 0.5844 0.8910 0.5121 0.035 Uiso 1 1 calc GR . . . .
H13C H 0.3836 0.8931 0.5137 0.035 Uiso 1 1 calc GR . . . .
C14 C 0.3820(3) 0.7284(2) 0.40260(6) 0.0160(4) Uani 1 1 d . . . . .
H14 H 0.3084 0.6597 0.3894 0.019 Uiso 1 1 calc R . . . .
C15 C 0.3715(3) 0.8582(2) 0.37770(6) 0.0156(4) Uani 1 1 d . . . . .
H15 H 0.4689 0.9172 0.3843 0.019 Uiso 1 1 calc R . . . .
C16 C 0.2037(3) 0.9316(2) 0.38493(6) 0.0197(4) Uani 1 1 d . . . . .
H16A H 0.1334 0.8860 0.4061 0.024 Uiso 1 1 calc R . . . .
H16B H 0.2219 1.0250 0.3936 0.024 Uiso 1 1 calc R . . . .
C17 C 0.2164(3) 1.0178(2) 0.31142(7) 0.0210(5) Uani 1 1 d . . . . .
H17A H 0.2355 1.1055 0.3247 0.025 Uiso 1 1 calc R . . . .
H17B H 0.1532 1.0298 0.2849 0.025 Uiso 1 1 calc R . . . .
C18 C 0.3833(3) 0.9427(2) 0.30405(6) 0.0172(4) Uani 1 1 d . . . . .
C19 C 0.5390(3) 1.0263(2) 0.31175(7) 0.0184(4) Uani 1 1 d . . . . .
H19A H 0.5348 1.1065 0.2938 0.022 Uiso 1 1 calc R . . . .
H19B H 0.5407 1.0557 0.3414 0.022 Uiso 1 1 calc R . . . .
C20 C 0.3953(3) 0.8922(2) 0.25887(6) 0.0185(4) Uani 1 1 d . . . . .
H20A H 0.3010 0.8307 0.2532 0.022 Uiso 1 1 calc R . . . .
H20B H 0.3862 0.9680 0.2392 0.022 Uiso 1 1 calc R . . . .
C21 C 0.6963(3) 0.9027(2) 0.26067(6) 0.0197(5) Uani 1 1 d . . . . .
C22 C 0.8409(3) 0.8074(2) 0.25994(7) 0.0232(5) Uani 1 1 d . . . . .
H22A H 0.8220 0.7371 0.2807 0.035 Uiso 1 1 calc GR . . . .
H22B H 0.9448 0.8549 0.2668 0.035 Uiso 1 1 calc GR . . . .
H22C H 0.8505 0.7680 0.2319 0.035 Uiso 1 1 calc GR . . . .
C23 C 0.7169(3) 1.0155(2) 0.22888(7) 0.0257(5) Uani 1 1 d . . . . .
H23A H 0.7200 0.9786 0.2004 0.039 Uiso 1 1 calc GR . . . .
H23B H 0.8217 1.0632 0.2345 0.039 Uiso 1 1 calc GR . . . .
H23C H 0.6220 1.0770 0.2313 0.039 Uiso 1 1 calc GR . . . .


_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 O3 1.6405(15) . ?
Si1 C4 1.888(2) . ?
Si1 C8 1.869(2) . ?
Si1 C9 1.865(2) . ?
O1 H1 0.82(3) . ?
O1 C1 1.429(2) . ?
O2 N1 1.465(2) . ?
O2 C2 1.459(2) . ?
O3 C3 1.421(2) . ?
O4 C10 1.436(2) . ?
O4 C11 1.421(2) . ?
O5 C11 1.444(2) . ?
O5 C14 1.439(2) . ?
O6 C19 1.429(3) . ?
O6 C21 1.438(2) . ?
O7 C20 1.427(3) . ?
O7 C21 1.427(3) . ?
N1 C15 1.504(2) . ?
N1 C18 1.506(2) . ?
C1 H1A 1.0000 . ?
C1 C3 1.518(3) . ?
C1 C10 1.518(3) . ?
C2 H2 1.0000 . ?
C2 C16 1.527(3) . ?
C2 C17 1.520(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.540(3) . ?
C4 C6 1.533(3) . ?
C4 C7 1.537(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
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 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 1.0000 . ?
C10 C14 1.523(3) . ?
C11 C12 1.520(3) . ?
C11 C13 1.509(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14 1.0000 . ?
C14 C15 1.530(3) . ?
C15 H15 1.0000 . ?
C15 C16 1.544(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.547(3) . ?
C18 C19 1.519(3) . ?
C18 C20 1.529(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.499(3) . ?
C21 C23 1.530(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
O3 Si1 C4 104.36(9) . . ?
O3 Si1 C8 108.94(10) . . ?
O3 Si1 C9 110.65(9) . . ?
C8 Si1 C4 112.46(10) . . ?
C9 Si1 C4 110.75(11) . . ?
C9 Si1 C8 109.57(11) . . ?
C1 O1 H1 103.3(19) . . ?
C2 O2 N1 97.50(14) . . ?
C3 O3 Si1 128.70(12) . . ?
C11 O4 C10 105.38(15) . . ?
C14 O5 C11 109.13(14) . . ?
C19 O6 C21 113.73(16) . . ?
C20 O7 C21 114.57(16) . . ?
O2 N1 C15 99.48(13) . . ?
O2 N1 C18 99.28(14) . . ?
C15 N1 C18 112.03(15) . . ?
O1 C1 H1A 109.4 . . ?
O1 C1 C3 109.01(16) . . ?
O1 C1 C10 109.20(17) . . ?
C3 C1 H1A 109.4 . . ?
C3 C1 C10 110.32(16) . . ?
C10 C1 H1A 109.4 . . ?
O2 C2 H2 114.0 . . ?
O2 C2 C16 101.54(15) . . ?
O2 C2 C17 101.72(16) . . ?
C16 C2 H2 114.0 . . ?
C17 C2 H2 114.0 . . ?
C17 C2 C16 110.12(18) . . ?
O3 C3 C1 110.65(16) . . ?
O3 C3 H3A 109.5 . . ?
O3 C3 H3B 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 Si1 109.62(15) . . ?
C6 C4 Si1 109.83(14) . . ?
C6 C4 C5 108.94(19) . . ?
C6 C4 C7 109.12(19) . . ?
C7 C4 Si1 110.79(15) . . ?
C7 C4 C5 108.50(18) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 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 . . ?
Si1 C9 H9A 109.5 . . ?
Si1 C9 H9B 109.5 . . ?
Si1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O4 C10 C1 109.02(16) . . ?
O4 C10 H10 108.8 . . ?
O4 C10 C14 101.55(15) . . ?
C1 C10 H10 108.8 . . ?
C1 C10 C14 119.21(16) . . ?
C14 C10 H10 108.8 . . ?
O4 C11 O5 105.21(14) . . ?
O4 C11 C12 111.28(17) . . ?
O4 C11 C13 109.11(17) . . ?
O5 C11 C12 108.81(17) . . ?
O5 C11 C13 109.73(18) . . ?
C13 C11 C12 112.45(17) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C14 C10 101.64(15) . . ?
O5 C14 H14 109.9 . . ?
O5 C14 C15 109.73(16) . . ?
C10 C14 H14 109.9 . . ?
C10 C14 C15 115.50(17) . . ?
C15 C14 H14 109.9 . . ?
N1 C15 C14 107.32(15) . . ?
N1 C15 H15 110.9 . . ?
N1 C15 C16 104.48(15) . . ?
C14 C15 H15 110.9 . . ?
C14 C15 C16 112.25(17) . . ?
C16 C15 H15 110.9 . . ?
C2 C16 C15 100.48(16) . . ?
C2 C16 H16A 111.7 . . ?
C2 C16 H16B 111.7 . . ?
C15 C16 H16A 111.7 . . ?
C15 C16 H16B 111.7 . . ?
H16A C16 H16B 109.4 . . ?
C2 C17 H17A 111.6 . . ?
C2 C17 H17B 111.6 . . ?
C2 C17 C18 100.90(16) . . ?
H17A C17 H17B 109.4 . . ?
C18 C17 H17A 111.6 . . ?
C18 C17 H17B 111.6 . . ?
N1 C18 C17 103.92(16) . . ?
N1 C18 C19 114.36(16) . . ?
N1 C18 C20 106.81(16) . . ?
C19 C18 C17 114.00(17) . . ?
C19 C18 C20 106.58(17) . . ?
C20 C18 C17 111.02(17) . . ?
O6 C19 C18 111.48(17) . . ?
O6 C19 H19A 109.3 . . ?
O6 C19 H19B 109.3 . . ?
C18 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
O7 C20 C18 110.79(17) . . ?
O7 C20 H20A 109.5 . . ?
O7 C20 H20B 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
O6 C21 C22 105.92(17) . . ?
O6 C21 C23 110.95(17) . . ?
O7 C21 O6 109.91(16) . . ?
O7 C21 C22 105.74(17) . . ?
O7 C21 C23 111.56(18) . . ?
C22 C21 C23 112.49(19) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Si1 O3 C3 C1 117.89(16) . . . . ?
O1 C1 C3 O3 -74.62(19) . . . . ?
O1 C1 C10 O4 -177.15(15) . . . . ?
O1 C1 C10 C14 -61.3(2) . . . . ?
O2 N1 C15 C14 83.82(17) . . . . ?
O2 N1 C15 C16 -35.53(17) . . . . ?
O2 N1 C18 C17 36.80(17) . . . . ?
O2 N1 C18 C19 161.70(16) . . . . ?
O2 N1 C18 C20 -80.65(18) . . . . ?
O2 C2 C16 C15 33.48(19) . . . . ?
O2 C2 C17 C18 -32.28(19) . . . . ?
O3 Si1 C4 C5 57.56(16) . . . . ?
O3 Si1 C4 C6 177.23(15) . . . . ?
O3 Si1 C4 C7 -62.15(17) . . . . ?
O4 C10 C14 O5 -36.30(18) . . . . ?
O4 C10 C14 C15 82.40(18) . . . . ?
O5 C14 C15 N1 -161.27(15) . . . . ?
O5 C14 C15 C16 -47.0(2) . . . . ?
N1 O2 C2 C16 -57.04(17) . . . . ?
N1 O2 C2 C17 56.60(16) . . . . ?
N1 C15 C16 C2 1.5(2) . . . . ?
N1 C18 C19 O6 63.0(2) . . . . ?
N1 C18 C20 O7 -68.3(2) . . . . ?
C1 C10 C14 O5 -155.99(17) . . . . ?
C1 C10 C14 C15 -37.3(2) . . . . ?
C2 O2 N1 C15 56.90(15) . . . . ?
C2 O2 N1 C18 -57.48(15) . . . . ?
C2 C17 C18 N1 -3.0(2) . . . . ?
C2 C17 C18 C19 -128.11(18) . . . . ?
C2 C17 C18 C20 111.51(18) . . . . ?
C3 C1 C10 O4 63.1(2) . . . . ?
C3 C1 C10 C14 178.88(17) . . . . ?
C4 Si1 O3 C3 -165.97(17) . . . . ?
C8 Si1 O3 C3 73.71(18) . . . . ?
C8 Si1 C4 C5 175.50(15) . . . . ?
C8 Si1 C4 C6 -64.84(18) . . . . ?
C8 Si1 C4 C7 55.78(19) . . . . ?
C9 Si1 O3 C3 -46.80(19) . . . . ?
C9 Si1 C4 C5 -61.53(18) . . . . ?
C9 Si1 C4 C6 58.13(18) . . . . ?
C9 Si1 C4 C7 178.75(16) . . . . ?
C10 O4 C11 O5 -30.00(19) . . . . ?
C10 O4 C11 C12 87.68(19) . . . . ?
C10 O4 C11 C13 -147.67(16) . . . . ?
C10 C1 C3 O3 45.3(2) . . . . ?
C10 C14 C15 N1 84.6(2) . . . . ?
C10 C14 C15 C16 -161.15(16) . . . . ?
C11 O4 C10 C1 168.01(16) . . . . ?
C11 O4 C10 C14 41.33(18) . . . . ?
C11 O5 C14 C10 19.0(2) . . . . ?
C11 O5 C14 C15 -103.74(18) . . . . ?
C14 O5 C11 O4 5.7(2) . . . . ?
C14 O5 C11 C12 -113.66(18) . . . . ?
C14 O5 C11 C13 122.93(17) . . . . ?
C14 C15 C16 C2 -114.49(18) . . . . ?
C15 N1 C18 C17 -67.45(19) . . . . ?
C15 N1 C18 C19 57.4(2) . . . . ?
C15 N1 C18 C20 175.09(16) . . . . ?
C16 C2 C17 C18 74.8(2) . . . . ?
C17 C2 C16 C15 -73.7(2) . . . . ?
C17 C18 C19 O6 -177.67(17) . . . . ?
C17 C18 C20 O7 179.07(16) . . . . ?
C18 N1 C15 C14 -172.05(16) . . . . ?
C18 N1 C15 C16 68.59(19) . . . . ?
C19 O6 C21 O7 -54.7(2) . . . . ?
C19 O6 C21 C22 -168.47(17) . . . . ?
C19 O6 C21 C23 69.2(2) . . . . ?
C19 C18 C20 O7 54.4(2) . . . . ?
C20 O7 C21 O6 55.2(2) . . . . ?
C20 O7 C21 C22 169.06(16) . . . . ?
C20 O7 C21 C23 -68.4(2) . . . . ?
C20 C18 C19 O6 -54.8(2) . . . . ?
C21 O6 C19 C18 57.2(2) . . . . ?
C21 O7 C20 C18 -57.2(2) . . . . ?





