#============================================================================= 
data_global
#=============================================================================  
# 1. SUBMISSION DETAILS 
 

_publ_contact_author_name           'Robert Britton'
_publ_contact_author_address 
; 
 Dept. of Chemistry, Simon Fraser University
 8888 University Drive
 Burnaby, B.C.
 Canada
 V5A 1S6
; 
 
_publ_contact_author_phone     778-782-4889
_publ_contact_author_fax        778-782-3765
_publ_contact_author_email      rbritton@sfu.ca
_publ_requested_journal             'Beilstein Journal of Organic Chemistry'  
#============================================================================= 
# 2. PROCESSING SUMMARY (IUCr Office Use Only) 
_journal_date_recd_electronic      ? 
_journal_date_to_coeditor          ? 
_journal_date_from_coeditor        ? 
_journal_date_accepted            ? 
_journal_date_printers_first       ? 
_journal_date_printers_final       ? 
_journal_date_proofs_out           ? 
_journal_date_proofs_in            ? 
_journal_coeditor_name             ? 
_journal_coeditor_code             ? 
_journal_coeditor_notes 
; 
 ? 
; 
_journal_techeditor_code           ? 
_journal_techeditor_notes 
; 
 ? 
; 
_journal_coden_ASTM                ? 
_journal_name_full                  ? 
_journal_year                       ? 
_journal_volume                     ? 
_journal_issue                      ? 
_journal_page_first                 ? 
_journal_page_last                  ? 
_journal_suppl_publ_number         ? 
_journal_suppl_publ_pages          ? 
 
#============================================================================= 
# 3. TITLE AND AUTHOR LIST 
 
_publ_section_title 
; 
Sequential Directed ortho Metalations of Hydrobenzoin: 
Rapid Access to Hydrobenzoin Analogues Useful for Asymmetric Synthesis
; 
 
# The loop structure below should contain the names and addresses of all 
# Authors, in the required order of publication. Repeat as necessary. 
loop_ 
 _publ_author_name 
 _publ_author_address 

  'Cho, Inhee'
; Department of Chemistry
 Simon Fraser University
 Burnaby, British Columbia
 Canada   V5A 1S6
;
 'Meimetis, Labros'
; Department of Chemistry
  Simon Fraser University
  Burnaby, British Columbia
  Canada   V5A 1S6
;
 'Belding, Lee'
; Department of Chemistry
 Simon Fraser University
 Burnaby, British Columbia
 Canada   V5A 1S6

 Department of Chemistry
 Brock University
 St. Catharines, Ontario
 Canada   L2S 3A1
;
 'Katz, Michael J.'
; Department of Chemistry
 Simon Fraser University
 Burnaby, British Columbia
 Canada   V5A 1S6
;
'Dudding, Travis'
;
 Department of Chemistry
 Brock University
 St. Catharines, Ontario
 Canada   L2S 3A1
;
 'Britton, Robert B.'
; Department of Chemistry
 Simon Fraser University
 Burnaby, British Columbia
 Canada   V5A 1S6
;

#============================================================================== 
# 4. TEXT
_publ_section_abstract
;
 ?  #Insert appropriate text here if wanted.
;
_publ_section_comment
;
 ?  #Insert appropriate text here if wanted.
;
_publ_section_experimental
;
 ?  #Insert appropriate text here if wanted.
;
## -------------------REFERENCES ----------------------##  
_publ_section_references 
;
 International Tables for X-ray Crystallography, Vol. IV, (1974)
 Kynoch Press, Birmingham, England.

 Johnson, C.K., (1976) ORTEP - A Fortran Thermal Ellipsoid Plot
 Program, Technical Report ORNL-5138, Oak Ridge National Lab., U.S.A.

# CRYSTALS
#
Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper
R.I. (2001) CRYSTALS
Issue 11. Chemical Crystallography Laboratory, OXFORD, UK.

# SIR92                                                                         
#                                                                               
Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C.,          
Polidori, G.  & Camalli, M. (1994) SIR92 - a program for automatic solution of  
crystal structures by direct methods. J. Appl. Cryst. (27), 435-435

 ?  #Insert any other references here
;
_publ_section_figure_captions
;
 ?  #Insert figure captions here if wanted
;
_publ_section_acknowledgements
;
 ?  #Insert any acknowledgements here.
;

#===============================================================================

# If more than one structure is reported, sections 5-10 should be filled in
# per structure.  For each data set, replace the ? in the data_? line below
# by a unique identifier.

data_C18_H22_O2_Si1
#===============================================================================
# 5. CHEMICAL DATA

_chemical_formula_sum 'C18 H22 O2 Si1'
_chemical_formula_moiety 'C18 H22 O2 Si1'
_chemical_formula_weight 298.46
#=============================================================
# 6. CRYSTAL DATA

_symmetry_cell_setting             'Orthorhombic' 
_symmetry_space_group_name_H-M    'P 21 21 21 ' 
loop_
_symmetry_equiv_pos_as_xyz
 'x,y,z'
 'x+1/2,-y+1/2,-z'
 '-x,y+1/2,-z+1/2'
 '-x+1/2,-y,z+1/2'

#------------------------------------------------
_cell_length_a                    6.82150(10)
_cell_length_b                    13.4340(3)
_cell_length_c                    17.9267(4)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1642.80(6)
_cell_formula_units_z               4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used    9841
_cell_measurement_theta_min        2.73
_cell_measurement_theta_max       34.68

  
_exptl_crystal_description       'Block'
_exptl_crystal_colour            'colourless'
_exptl_crystal_size_min          0.178
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_max          0.494
 
_exptl_crystal_density_diffrn       1.207
_exptl_crystal_density_meas         ? 
# Non-dispersive F(000): 
_exptl_crystal_F_000                640 
_exptl_absorpt_coefficient_mu       0.145
_exptl_absorpt_correction_type      numerical
_exptl_absorpt_correction_t_min     0.92
_exptl_absorpt_correction_t_max     0.97

loop_
 _exptl_crystal_face_index_h
 _exptl_crystal_face_index_k
 _exptl_crystal_face_index_l
 _exptl_crystal_face_perp_dist
    0.00   -2.00    1.00    0.1070
    0.00    2.00   -1.00    0.0720
    0.00   -1.00    1.00    0.0890
    0.00    1.00   -1.00    0.0820
   -1.00    1.00    1.00    0.1810
    1.00   -1.00   -1.00    0.2320
    2.00    0.00    1.00    0.2230
    0.00    1.00    2.00    0.1150
    0.00   -1.00   -2.00    0.1000
    1.00    1.00    2.00    0.1790
   -2.00   -2.00   -1.00    0.2340
   -1.00   -2.00    1.00    0.1880
    0.00   -1.00    2.00    0.1060
   -1.00    2.00   -1.00    0.1530
   -1.00    1.00    2.00    0.1690


#=============================================================================
# 7. EXPERIMENTAL DATA

_diffrn_radiation_type                 'MoK\a'
_diffrn_radiation_wavelength           0.71073
_diffrn_measurement_device_type       'Apex II CCD (Bruker AXS)'
_diffrn_radiation_monochromator       'graphite crystal'
_diffrn_measurement_method             '0.5 degree φ & ω scans' 
_diffrn_ambient_temperature            150(2)
_diffrn_reflns_number                 63558 
_diffrn_reflns_av_R_equivalents       0.037 
_diffrn_reflns_theta_min          1.894 
_diffrn_reflns_theta_max          34.968 
_diffrn_measured_fraction_theta_max 0.990 
_diffrn_reflns_theta_full         33.219 
_diffrn_measured_fraction_theta_full 0.997 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -20 
_diffrn_reflns_limit_k_max        20 
_diffrn_reflns_limit_l_min        -28 
_diffrn_reflns_limit_l_max        27 

#==========================================================================
# 8. REFINEMENT DATA

# The I/u(I) cutoff below was used for refinement as 
# well as the _gt R-factors:

# Number of reflections with Friedels Law is 4007 
# Number of reflections without Friedels Law is 7111 
# Theoretical number of reflections is about 3608 

_reflns_number_total                7111
_refine_ls_structure_factor_coef    F
_refine_ls_number_reflns          4784 
_refine_ls_number_restraints      0 
_refine_ls_number_parameters      193 

_refine_ls_shift/su_max           0.000938 
_refine_diff_density_max            0.25
_refine_diff_density_min            -0.17

#_refine_ls_R_factor_ref 0.0291 
_refine_ls_wR_factor_ref          0.0342 
_refine_ls_goodness_of_fit_ref    0.7515 
 
#_reflns_number_all 7111 
_refine_ls_R_factor_all           0.0427 
_refine_ls_wR_factor_all          0.0573 
 
# The I/u(I) cutoff below was used for refinement as 
# well as the _gt R-factors:
_reflns_threshold_expression      I>2.5σ(I)
_reflns_number_gt                 4784 
_refine_ls_R_factor_gt            0.0291 
_refine_ls_wR_factor_gt           0.0342 

_refine_ls_abs_structure_Flack    0.02(8) 
_refine_ls_abs_structure_details  'Flack (1983), 3104 Friedel-pairs' 
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration  'ad' 

_refine_ls_weighting_scheme         calc
_refine_ls_weighting_details 
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.02P)²] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

_oxford_refine_ls_scale 0.2346(2) 
_oxford_diffrn_Wilson_B_factor    1.76 
_oxford_diffrn_Wilson_scale       19.75 

_reflns_limit_h_min               -10 
_reflns_limit_h_max               10 
_reflns_limit_k_min               0 
_reflns_limit_k_max               20 
_reflns_limit_l_min               0 
_reflns_limit_l_max               28 
 
#---------------------------------------------------------
_chemical_name_systematic        
; 
; 
# choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' 
_refine_ls_matrix_type              full
 
# choose from 'heavy, direct, difmap, geom' 
_atom_sites_solution_primary        direct
 
# _atom_sites_solution_secondary difmap 
_atom_sites_solution_hydrogens      geom
 
# choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' 
_refine_ls_hydrogen_treatment       constr

# none if no extinction, 
_refine_ls_extinction_method   none

#========================================================== 
# 9. General computing 
_computing_data_collection      'Bruker SMART'
_computing_cell_refinement      'Bruker SMART'
_computing_data_reduction       'Bruker SAINT'
_computing_structure_solution   'Sir 9x'
_computing_structure_refinement 'Crystals'
_computing_molecular_graphics   'Ortep-3'
#===================================================================
# 10.  ATOMIC COORDINATES AND THERMAL PARAMETERS
 
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source  
 C       0.0033   0.0016   2.3100  20.8439   1.0200  10.2075   1.5886   0.5687
   0.8650  51.6512   0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 H       0.0000   0.0000   0.4930  10.5109   0.3229  26.1257   0.1402   3.1424
   0.0408  57.7998   0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 O       0.0106   0.0060   3.0485  13.2771   2.2868   5.7011   1.5463   0.3239
   0.8670  32.9089   0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 Si      0.0817   0.0704   6.2915   2.4386   3.0353  32.3337   1.9891   0.6785
   1.5410  81.6937   1.1407 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 
#==============================================================================
# Uequiv = arithmetic mean of Ui
# i.e. Ueqiv = (U1+U2+U3)/3

# Replace trailing . with the number of unfound
# hydrogen atoms attaced to relavent atom

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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Si1 Si -0.09735(5) 0.57874(2) 0.600176(19) 0.0235 1.0000 Uani . . . . . . 
O1 O -0.24106(12) 0.35561(6) 0.61992(4) 0.0210 1.0000 Uani . . . . . . 
O2 O 0.25090(12) 0.39344(6) 0.56601(4) 0.0215 1.0000 Uani . . . . . . 
C1 C 0.03194(17) 0.51441(10) 0.67935(6) 0.0229 1.0000 Uani . . . . . . 
C2 C 0.1198(2) 0.57496(11) 0.73351(7) 0.0316 1.0000 Uani . . . . . . 
C3 C 0.2211(2) 0.53521(13) 0.79389(7) 0.0396 1.0000 Uani . . . . . . 
C4 C 0.2357(2) 0.43334(13) 0.80185(7) 0.0373 1.0000 Uani . . . . . . 
C5 C 0.14891(18) 0.37158(11) 0.74926(7) 0.0285 1.0000 Uani . . . . . . 
C6 C 0.04819(15) 0.41099(9) 0.68826(6) 0.0209 1.0000 Uani . . . . . . 
C7 C -0.03595(16) 0.34047(9) 0.63092(6) 0.0186 1.0000 Uani . . . . . . 
C8 C 0.06161(16) 0.35088(8) 0.55321(6) 0.0181 1.0000 Uani . . . . . . 
C9 C -0.05619(15) 0.40937(8) 0.49693(6) 0.0180 1.0000 Uani . . . . . . 
C10 C -0.09898(19) 0.36327(9) 0.42914(6) 0.0237 1.0000 Uani . . . . . . 
C11 C -0.19958(18) 0.41401(12) 0.37329(7) 0.0303 1.0000 Uani . . . . . . 
C12 C -0.2552(2) 0.51128(11) 0.38456(7) 0.0315 1.0000 Uani . . . . . . 
C13 C -0.21461(19) 0.55711(10) 0.45218(7) 0.0271 1.0000 Uani . . . . . . 
C14 C -0.11663(17) 0.50741(8) 0.51018(6) 0.0201 1.0000 Uani . . . . . . 
C15 C -0.35606(18) 0.33662(10) 0.68453(7) 0.0276 1.0000 Uani . . . . . . 
C16 C 0.36334(17) 0.40472(10) 0.49952(7) 0.0264 1.0000 Uani . . . . . . 
C17 C -0.3515(2) 0.61315(12) 0.63027(9) 0.0378 1.0000 Uani . . . . . . 
C18 C 0.0413(3) 0.69552(11) 0.57819(9) 0.0427 1.0000 Uani . . . . . . 
H21 H 0.1099 0.6478 0.7302 0.0353(12) 1.0000 Uiso R . . . . . 
H31 H 0.2789 0.5778 0.8297 0.0417(12) 1.0000 Uiso R . . . . . 
H41 H 0.3045 0.4067 0.8438 0.0378(12) 1.0000 Uiso R . . . . . 
H51 H 0.1578 0.2986 0.7557 0.0272(12) 1.0000 Uiso R . . . . . 
H71 H -0.0156 0.2700 0.6484 0.0148(12) 1.0000 Uiso R . . . . . 
H81 H 0.0805 0.2811 0.5335 0.0146(12) 1.0000 Uiso R . . . . . 
H101 H -0.0546 0.2934 0.4200 0.0221(12) 1.0000 Uiso R . . . . . 
H111 H -0.2256 0.3814 0.3272 0.0294(12) 1.0000 Uiso R . . . . . 
H121 H -0.3228 0.5461 0.3462 0.0316(12) 1.0000 Uiso R . . . . . 
H131 H -0.2535 0.6244 0.4586 0.0277(12) 1.0000 Uiso R . . . . . 
H151 H -0.4924 0.3462 0.6725 0.0421 1.0000 Uiso R . . . . . 
H152 H -0.3206 0.3815 0.7256 0.0398(15) 1.0000 Uiso R . . . . . 
H153 H -0.3392 0.2680 0.7034 0.0399(15) 1.0000 Uiso R . . . . . 
H161 H 0.4986 0.4130 0.5147 0.0391(15) 1.0000 Uiso R . . . . . 
H162 H 0.3233 0.4632 0.4709 0.0396(15) 1.0000 Uiso R . . . . . 
H163 H 0.3542 0.3438 0.4677 0.0382(15) 1.0000 Uiso R . . . . . 
H171 H -0.4147 0.6535 0.5919 0.0568(15) 1.0000 Uiso R . . . . . 
H172 H -0.3449 0.6552 0.6749 0.0576(15) 1.0000 Uiso R . . . . . 
H173 H -0.4304 0.5542 0.6399 0.0577(15) 1.0000 Uiso R . . . . . 
H181 H -0.0196 0.7279 0.5353 0.0629(15) 1.0000 Uiso R . . . . . 
H182 H 0.0340 0.7405 0.6191 0.0618(15) 1.0000 Uiso R . . . . . 
H183 H 0.1811 0.6828 0.5695 0.0632(15) 1.0000 Uiso R . . . . . 


loop_
 _geom_bond_atom_site_label_1
 _geom_bond_site_symmetry_1
 _geom_bond_atom_site_label_2
 _geom_bond_site_symmetry_2
 _geom_bond_distance
 _geom_bond_publ_flag
Si1 . C1 . 1.8812(13)    yes
Si1 . C14 . 1.8811(11)    yes
Si1 . C17 . 1.8738(15)    yes
Si1 . C18 . 1.8738(15)    yes
O1 . C7 . 1.4275(13)    yes
O1 . C15 . 1.4220(14)    yes
O2 . C8 . 1.4307(13)    yes
O2 . C16 . 1.4255(14)    yes
C1 . C2 . 1.4013(16)    yes
C1 . C6 . 1.4030(18)    yes
C2 . C3 . 1.391(2)    yes
C2 . H21 . 0.982    no
C3 . C4 . 1.380(2)    yes
C3 . H31 . 0.947    no
C4 . C5 . 1.3885(19)    yes
C4 . H41 . 0.955    no
C5 . C6 . 1.3957(16)    yes
C5 . H51 . 0.989    no
C6 . C7 . 1.5112(16)    yes
C7 . C8 . 1.5501(15)    yes
C7 . H71 . 1.006    no
C8 . C9 . 1.5103(15)    yes
C8 . H81 . 1.010    no
C9 . C10 . 1.3948(15)    yes
C9 . C14 . 1.4004(16)    yes
C10 . C11 . 1.3921(18)    yes
C10 . H101 . 1.000    no
C11 . C12 . 1.376(2)    yes
C11 . H111 . 0.952    no
C12 . C13 . 1.3875(19)    yes
C12 . H121 . 0.951    no
C13 . C14 . 1.4049(16)    yes
C13 . H131 . 0.949    no
C15 . H151 . 0.964    no
C15 . H152 . 0.981    no
C15 . H153 . 0.988    no
C16 . H161 . 0.968    no
C16 . H162 . 0.977    no
C16 . H163 . 1.000    no
C17 . H171 . 0.976    no
C17 . H172 . 0.980    no
C17 . H173 . 0.972    no
C18 . H181 . 0.976    no
C18 . H182 . 0.951    no
C18 . H183 . 0.981    no

loop_
 _geom_angle_atom_site_label_1
 _geom_angle_site_symmetry_1
 _geom_angle_atom_site_label_2
 _geom_angle_site_symmetry_2
 _geom_angle_atom_site_label_3
 _geom_angle_site_symmetry_3
 _geom_angle
 _geom_angle_publ_flag
C1 . Si1 . C14 . 116.48(5)    yes
C1 . Si1 . C17 . 109.26(6)    yes
C14 . Si1 . C17 . 107.93(6)    yes
C1 . Si1 . C18 . 107.86(7)    yes
C14 . Si1 . C18 . 106.34(6)    yes
C17 . Si1 . C18 . 108.73(8)    yes
C7 . O1 . C15 . 113.74(9)    yes
C8 . O2 . C16 . 113.20(9)    yes
Si1 . C1 . C2 . 117.17(10)    yes
Si1 . C1 . C6 . 125.31(9)    yes
C2 . C1 . C6 . 117.52(12)    yes
C1 . C2 . C3 . 121.94(14)    yes
C1 . C2 . H21 . 120.4    no
C3 . C2 . H21 . 117.6    no
C2 . C3 . C4 . 119.82(13)    yes
C2 . C3 . H31 . 120.2    no
C4 . C3 . H31 . 120.0    no
C3 . C4 . C5 . 119.46(13)    yes
C3 . C4 . H41 . 119.3    no
C5 . C4 . H41 . 121.3    no
C4 . C5 . C6 . 121.01(14)    yes
C4 . C5 . H51 . 119.2    no
C6 . C5 . H51 . 119.8    no
C1 . C6 . C5 . 120.26(11)    yes
C1 . C6 . C7 . 120.88(10)    yes
C5 . C6 . C7 . 118.82(12)    yes
C6 . C7 . O1 . 112.14(9)    yes
C6 . C7 . C8 . 113.06(9)    yes
O1 . C7 . C8 . 106.49(9)    yes
C6 . C7 . H71 . 109.0    no
O1 . C7 . H71 . 108.2    no
C8 . C7 . H71 . 107.8    no
C7 . C8 . O2 . 106.22(8)    yes
C7 . C8 . C9 . 114.76(9)    yes
O2 . C8 . C9 . 112.30(9)    yes
C7 . C8 . H81 . 106.5    no
O2 . C8 . H81 . 108.2    no
C9 . C8 . H81 . 108.5    no
C8 . C9 . C10 . 117.54(10)    yes
C8 . C9 . C14 . 122.18(10)    yes
C10 . C9 . C14 . 120.25(10)    yes
C9 . C10 . C11 . 120.82(12)    yes
C9 . C10 . H101 . 119.8    no
C11 . C10 . H101 . 119.4    no
C10 . C11 . C12 . 119.70(12)    yes
C10 . C11 . H111 . 119.4    no
C12 . C11 . H111 . 120.9    no
C11 . C12 . C13 . 119.66(12)    yes
C11 . C12 . H121 . 119.7    no
C13 . C12 . H121 . 120.6    no
C12 . C13 . C14 . 122.05(12)    yes
C12 . C13 . H131 . 118.2    no
C14 . C13 . H131 . 119.7    no
C13 . C14 . C9 . 117.48(11)    yes
C13 . C14 . Si1 . 115.21(9)    yes
C9 . C14 . Si1 . 127.16(8)    yes
O1 . C15 . H151 . 109.0    no
O1 . C15 . H152 . 111.4    no
H151 . C15 . H152 . 108.9    no
O1 . C15 . H153 . 112.4    no
H151 . C15 . H153 . 108.3    no
H152 . C15 . H153 . 106.7    no
O2 . C16 . H161 . 106.8    no
O2 . C16 . H162 . 112.0    no
H161 . C16 . H162 . 108.8    no
O2 . C16 . H163 . 110.9    no
H161 . C16 . H163 . 108.3    no
H162 . C16 . H163 . 110.0    no
Si1 . C17 . H171 . 110.0    no
Si1 . C17 . H172 . 109.6    no
H171 . C17 . H172 . 106.0    no
Si1 . C17 . H173 . 111.2    no
H171 . C17 . H173 . 109.5    no
H172 . C17 . H173 . 110.4    no
Si1 . C18 . H181 . 108.9    no
Si1 . C18 . H182 . 110.1    no
H181 . C18 . H182 . 107.5    no
Si1 . C18 . H183 . 112.2    no
H181 . C18 . H183 . 111.5    no
H182 . C18 . H183 . 106.5    no



data_C18_H22_O2_Si2
#===============================================================================
# 5. CHEMICAL DATA

_chemical_formula_sum             'C18 H22 O2 Si2'
_chemical_formula_moiety          'C18 H22 O2 Si2'
_chemical_formula_weight 326.54
#=============================================================
# 6. CRYSTAL DATA

_symmetry_cell_setting             'Monoclinic'
_symmetry_space_group_name_H-M    'P 1 21 1' 
loop_
_symmetry_equiv_pos_as_xyz
 'x,y,z'
 '-x,y+1/2,-z'

#------------------------------------------------
_cell_length_a                    8.855(4)
_cell_length_b                    28.605(14)
_cell_length_c                    11.190(5)
_cell_angle_alpha                 90
_cell_angle_beta                  96.194(7)
_cell_angle_gamma                 90
_cell_volume                      2818(2)
_cell_formula_units_z              6
_cell_measurement_temperature     293
_cell_measurement_reflns_used    5854
_cell_measurement_theta_min        2.31
_cell_measurement_theta_max       20.36

  
_exptl_crystal_description       'plate'
_exptl_crystal_colour            'colourless'
_exptl_crystal_size_min          0.03
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_max          0.46
 
_exptl_crystal_density_diffrn       1.154
_exptl_crystal_density_meas         ? 
# Non-dispersive F(000): 
_exptl_crystal_F_000                1044
_exptl_absorpt_coefficient_mu       0.193
_exptl_absorpt_correction_type      multi-scan
_exptl_absorpt_correction_t_min     0.95
_exptl_absorpt_correction_t_max     1.00

#=============================================================================
# 7. EXPERIMENTAL DATA

_diffrn_radiation_type                 'MoK\a'
_diffrn_radiation_wavelength           0.71073
_diffrn_measurement_device_type       'Apex II CCD (Bruker AXS)'
_diffrn_radiation_monochromator       'graphite crystal'
_diffrn_measurement_method             '0.5 degree φ & ω scans' 
_diffrn_ambient_temperature            293
_diffrn_reflns_number                33314 
_diffrn_reflns_av_R_equivalents       0.088 
_diffrn_reflns_theta_min          1.424 
_diffrn_reflns_theta_max          28.556 
_diffrn_measured_fraction_theta_max 0.942
_diffrn_reflns_theta_full         27.128 
_diffrn_measured_fraction_theta_full 0.995 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -38 
_diffrn_reflns_limit_k_max        37 
_diffrn_reflns_limit_l_min        -15 
_diffrn_reflns_limit_l_max        14 

#==========================================================================
# 8. REFINEMENT DATA

# The I/u(I) cutoff below was used for refinement as 
# well as the _gt R-factors:

# Number of reflections with Friedels Law is 4007 
# Number of reflections without Friedels Law is 7111 
# Theoretical number of reflections is about 3608 

_reflns_number_total                13085 
_refine_ls_structure_factor_coef    F
_refine_ls_number_reflns          3832 
_refine_ls_number_restraints      1 
_refine_ls_number_parameters      599 

_refine_ls_shift/su_max          0.000172 
_refine_diff_density_max          0.12 
_refine_diff_density_min          -0.11 


#_refine_ls_R_factor_ref 0.0346 
_refine_ls_wR_factor_ref          0.0267 
_refine_ls_goodness_of_fit_ref    0.8073 
 
#_reflns_number_all 13085 
_refine_ls_R_factor_all           0.1700 
_refine_ls_wR_factor_all          0.0663 
 
# The I/u(I) cutoff below was used for refinement as 
# well as the _gt R-factors:
_reflns_threshold_expression      I>2.5σ(I)
_reflns_number_gt                 3832 
_refine_ls_R_factor_gt            0.0346 
_refine_ls_wR_factor_gt           0.0267 
 
_refine_ls_abs_structure_Flack    -0.02(10) 
_refine_ls_abs_structure_details  'Flack (1983), 6187 Friedel-pairs' 
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration  'ad' 


_refine_ls_weighting_scheme         calc
_refine_ls_weighting_details 
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.00P)²] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

_oxford_refine_ls_scale 0.19169(19)  
_oxford_diffrn_Wilson_B_factor    3.00 
_oxford_diffrn_Wilson_scale       49.79

_reflns_limit_h_min               -11 
_reflns_limit_h_max               11 
_reflns_limit_k_min               -38 
_reflns_limit_k_max               37 
_reflns_limit_l_min               0 
_reflns_limit_l_max               15 
 
#---------------------------------------------------------
_chemical_name_systematic        
; 
; 
# choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' 
_refine_ls_matrix_type              full
 
# choose from 'heavy, direct, difmap, geom' 
_atom_sites_solution_primary        direct
 
# _atom_sites_solution_secondary difmap 
_atom_sites_solution_hydrogens      geom
 
# choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' 
_refine_ls_hydrogen_treatment       constr

# none if no extinction, 
_refine_ls_extinction_method   none

#========================================================== 
# 9. General computing 
_computing_data_collection      'Bruker SMART'
_computing_cell_refinement      'Bruker SMART'
_computing_data_reduction       'Bruker SAINT'
_computing_structure_solution   'Sir 9x'
_computing_structure_refinement 'Crystals'
_computing_molecular_graphics   'Ortep-3'
#===================================================================
# 10.  ATOMIC COORDINATES AND THERMAL PARAMETERS
 
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source  
 C       0.0033   0.0016   2.3100  20.8439   1.0200  10.2075   1.5886   0.5687
   0.8650  51.6512   0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 H       0.0000   0.0000   0.4930  10.5109   0.3229  26.1257   0.1402   3.1424
   0.0408  57.7998   0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 O       0.0106   0.0060   3.0485  13.2771   2.2868   5.7011   1.5463   0.3239
   0.8670  32.9089   0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 Si      0.0817   0.0704   6.2915   2.4386   3.0353  32.3337   1.9891   0.6785
   1.5410  81.6937   1.1407 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 
 
#==============================================================================
# Uequiv = arithmetic mean of Ui
# i.e. Ueqiv = (U1+U2+U3)/3

# Replace trailing . with the number of unfound
# hydrogen atoms attaced to relavent atom

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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Si11 Si 0.4290(2) 0.16799(7) -0.06621(17) 0.0700 1.0000 Uani . . . . . . 
Si12 Si 0.4793(2) 0.28264(7) -0.32272(16) 0.0616 1.0000 Uani . . . . . . 
Si21 Si 0.9717(2) 0.30580(7) 0.37073(17) 0.0598 1.0000 Uani . . . . . . 
Si22 Si 0.8369(2) 0.42316(7) 0.13143(16) 0.0647 1.0000 Uani . . . . . . 
Si31 Si 1.0899(2) 0.54832(7) 0.69792(18) 0.0754 1.0000 Uani . . . . . . 
Si32 Si 1.1217(2) 0.58915(7) 0.32036(18) 0.0742 1.0000 Uani . . . . . . 
O11 O 0.4425(4) 0.17676(13) -0.2091(3) 0.0654 1.0000 Uani . . . . . . 
O12 O 0.3474(4) 0.27325(13) -0.2324(3) 0.0688 1.0000 Uani . . . . . . 
O21 O 0.8333(5) 0.31717(13) 0.2645(3) 0.0688 1.0000 Uani . . . . . . 
O22 O 0.8665(4) 0.41608(12) 0.2784(3) 0.0634 1.0000 Uani . . . . . . 
O31 O 1.1691(4) 0.53105(14) 0.5799(3) 0.0657 1.0000 Uani . . . . . . 
O32 O 0.9778(4) 0.57814(13) 0.3987(4) 0.0724 1.0000 Uani . . . . . . 
C111 C 0.5993(6) 0.1932(2) 0.0203(5) 0.1102 1.0000 Uani . . . . . . 
C112 C 0.4171(8) 0.1044(2) -0.0344(7) 0.1333 1.0000 Uani . . . . . . 
C113 C 0.2519(6) 0.1984(2) -0.0378(6) 0.0563 1.0000 Uani . . . . . . 
C114 C 0.1873(8) 0.1930(2) 0.0705(6) 0.0741 1.0000 Uani . . . . . . 
C115 C 0.0567(9) 0.2168(3) 0.0897(7) 0.0825 1.0000 Uani . . . . . . 
C116 C -0.0114(7) 0.2469(3) 0.0048(8) 0.0819 1.0000 Uani . . . . . . 
C117 C 0.0524(7) 0.25227(19) -0.1015(6) 0.0613 1.0000 Uani . . . . . . 
C118 C 0.1810(7) 0.2284(2) -0.1248(5) 0.0489 1.0000 Uani . . . . . . 
C119 C 0.2443(6) 0.2354(2) -0.2431(5) 0.0507 1.0000 Uani . . . . . . 
C121 C 0.6696(6) 0.2796(2) -0.2390(6) 0.1013 1.0000 Uani . . . . . . 
C122 C 0.4510(7) 0.34165(18) -0.3924(5) 0.0816 1.0000 Uani . . . . . . 
C123 C 0.4463(7) 0.2358(2) -0.4375(6) 0.0585 1.0000 Uani . . . . . . 
C124 C 0.4966(7) 0.2383(2) -0.5522(7) 0.0803 1.0000 Uani . . . . . . 
C125 C 0.4632(10) 0.2033(3) -0.6358(7) 0.1069 1.0000 Uani . . . . . . 
C126 C 0.3810(10) 0.1657(3) -0.6100(7) 0.1041 1.0000 Uani . . . . . . 
C127 C 0.3296(8) 0.1616(2) -0.4988(7) 0.0815 1.0000 Uani . . . . . . 
C128 C 0.3630(7) 0.1964(2) -0.4131(6) 0.0535 1.0000 Uani . . . . . . 
C129 C 0.3140(6) 0.19072(19) -0.2887(5) 0.0526 1.0000 Uani . . . . . . 
C211 C 1.1551(6) 0.3134(2) 0.3095(5) 0.0823 1.0000 Uani . . . . . . 
C212 C 0.9502(7) 0.24490(18) 0.4258(5) 0.0832 1.0000 Uani . . . . . . 
C213 C 0.9411(7) 0.34840(19) 0.4935(5) 0.0491 1.0000 Uani . . . . . . 
C214 C 1.0158(7) 0.3434(2) 0.6099(7) 0.0676 1.0000 Uani . . . . . . 
C215 C 0.9848(8) 0.3735(2) 0.7017(6) 0.0778 1.0000 Uani . . . . . . 
C216 C 0.8767(8) 0.4080(2) 0.6778(6) 0.0672 1.0000 Uani . . . . . . 
C217 C 0.8042(6) 0.41347(18) 0.5651(6) 0.0547 1.0000 Uani . . . . . . 
C218 C 0.8366(6) 0.38442(19) 0.4707(5) 0.0435 1.0000 Uani . . . . . . 
C219 C 0.7614(6) 0.39181(19) 0.3453(5) 0.0487 1.0000 Uani . . . . . . 
C221 C 0.9999(7) 0.4009(2) 0.0600(5) 0.0939 1.0000 Uani . . . . . . 
C222 C 0.8132(8) 0.48658(19) 0.0978(5) 0.1014 1.0000 Uani . . . . . . 
C223 C 0.6627(7) 0.3899(2) 0.0857(6) 0.0559 1.0000 Uani . . . . . . 
C224 C 0.5707(9) 0.3976(2) -0.0220(6) 0.0800 1.0000 Uani . . . . . . 
C225 C 0.4389(10) 0.3717(3) -0.0513(7) 0.0957 1.0000 Uani . . . . . . 
C226 C 0.3963(8) 0.3377(3) 0.0226(8) 0.0956 1.0000 Uani . . . . . . 
C227 C 0.4843(8) 0.3291(2) 0.1319(7) 0.0680 1.0000 Uani . . . . . . 
C228 C 0.6150(7) 0.3555(2) 0.1625(6) 0.0533 1.0000 Uani . . . . . . 
C229 C 0.7077(7) 0.3468(2) 0.2817(5) 0.0533 1.0000 Uani . . . . . . 
C311 C 1.1502(8) 0.6096(2) 0.7313(6) 0.1184 1.0000 Uani . . . . . . 
C312 C 1.1514(8) 0.5108(2) 0.8281(6) 0.1186 1.0000 Uani . . . . . . 
C313 C 0.8832(7) 0.5429(2) 0.6533(7) 0.0652 1.0000 Uani . . . . . . 
C314 C 0.7749(10) 0.5433(2) 0.7351(6) 0.0856 1.0000 Uani . . . . . . 
C315 C 0.6229(10) 0.5389(3) 0.6972(9) 0.1010 1.0000 Uani . . . . . . 
C316 C 0.5702(9) 0.5338(3) 0.5769(9) 0.0973 1.0000 Uani . . . . . . 
C317 C 0.6759(8) 0.53284(19) 0.4949(6) 0.0741 1.0000 Uani . . . . . . 
C318 C 0.8306(7) 0.53667(19) 0.5321(7) 0.0589 1.0000 Uani . . . . . . 
C319 C 0.9412(7) 0.5323(2) 0.4382(5) 0.0577 1.0000 Uani . . . . . . 
C321 C 1.2464(7) 0.6337(2) 0.3981(6) 0.1137 1.0000 Uani . . . . . . 
C322 C 1.0522(7) 0.6094(2) 0.1671(6) 0.1059 1.0000 Uani . . . . . . 
C323 C 1.2163(6) 0.5314(2) 0.3106(6) 0.0607 1.0000 Uani . . . . . . 
C324 C 1.3107(7) 0.5207(3) 0.2211(6) 0.0832 1.0000 Uani . . . . . . 
C325 C 1.3715(8) 0.4761(3) 0.2128(7) 0.0956 1.0000 Uani . . . . . . 
C326 C 1.3405(8) 0.4425(3) 0.2930(8) 0.0898 1.0000 Uani . . . . . . 
C327 C 1.2474(7) 0.4521(2) 0.3794(6) 0.0740 1.0000 Uani . . . . . . 
C328 C 1.1867(6) 0.4959(2) 0.3888(6) 0.0532 1.0000 Uani . . . . . . 
C329 C 1.0843(6) 0.50572(19) 0.4847(6) 0.0549 1.0000 Uani . . . . . . 
H1111 H 0.6035 0.2274 0.0029 0.149(5) 1.0000 Uiso R . . . . . 
H1112 H 0.6912 0.1775 -0.0058 0.149(5) 1.0000 Uiso R . . . . . 
H1113 H 0.5967 0.1883 0.1086 0.149(5) 1.0000 Uiso R . . . . . 
H1121 H 0.3227 0.0918 -0.0803 0.167(5) 1.0000 Uiso R . . . . . 
H1122 H 0.5078 0.0882 -0.0609 0.167(5) 1.0000 Uiso R . . . . . 
H1123 H 0.4132 0.0990 0.0535 0.167(5) 1.0000 Uiso R . . . . . 
H1141 H 0.2353 0.1715 0.1340 0.089(4) 1.0000 Uiso R . . . . . 
H1151 H 0.0083 0.2118 0.1654 0.086(4) 1.0000 Uiso R . . . . . 
H1161 H -0.1030 0.2652 0.0214 0.087(4) 1.0000 Uiso R . . . . . 
H1171 H 0.0032 0.2735 -0.1652 0.065(4) 1.0000 Uiso R . . . . . 
H1191 H 0.1570 0.2443 -0.3029 0.046(6) 1.0000 Uiso R . . . . . 
H1211 H 0.6863 0.2480 -0.2015 0.138(5) 1.0000 Uiso R . . . . . 
H1212 H 0.7484 0.2855 -0.2948 0.138(5) 1.0000 Uiso R . . . . . 
H1213 H 0.6772 0.3040 -0.1747 0.138(5) 1.0000 Uiso R . . . . . 
H1221 H 0.3475 0.3423 -0.4380 0.114(5) 1.0000 Uiso R . . . . . 
H1222 H 0.5291 0.3478 -0.4487 0.114(5) 1.0000 Uiso R . . . . . 
H1223 H 0.4579 0.3663 -0.3286 0.114(5) 1.0000 Uiso R . . . . . 
H1241 H 0.5644 0.2645 -0.5716 0.089(4) 1.0000 Uiso R . . . . . 
H1251 H 0.4982 0.2069 -0.7174 0.111(4) 1.0000 Uiso R . . . . . 
H1261 H 0.3626 0.1411 -0.6733 0.121(4) 1.0000 Uiso R . . . . . 
H1271 H 0.2637 0.1347 -0.4807 0.091(4) 1.0000 Uiso R . . . . . 
H1291 H 0.2367 0.1651 -0.2923 0.041(6) 1.0000 Uiso R . . . . . 
H2111 H 1.1617 0.3464 0.2811 0.135(5) 1.0000 Uiso R . . . . . 
H2112 H 1.2397 0.3072 0.3742 0.135(5) 1.0000 Uiso R . . . . . 
H2113 H 1.1634 0.2916 0.2408 0.135(5) 1.0000 Uiso R . . . . . 
H2121 H 0.8501 0.2406 0.4580 0.129(5) 1.0000 Uiso R . . . . . 
H2122 H 1.0341 0.2384 0.4909 0.129(5) 1.0000 Uiso R . . . . . 
H2123 H 0.9578 0.2228 0.3575 0.129(5) 1.0000 Uiso R . . . . . 
H2141 H 1.0920 0.3178 0.6267 0.078(4) 1.0000 Uiso R . . . . . 
H2151 H 1.0381 0.3705 0.7848 0.085(4) 1.0000 Uiso R . . . . . 
H2161 H 0.8487 0.4287 0.7440 0.081(4) 1.0000 Uiso R . . . . . 
H2171 H 0.7292 0.4394 0.5483 0.055(4) 1.0000 Uiso R . . . . . 
H2191 H 0.6707 0.4123 0.3502 0.043(6) 1.0000 Uiso R . . . . . 
H2211 H 1.0140 0.3668 0.0781 0.125(5) 1.0000 Uiso R . . . . . 
H2212 H 1.0925 0.4184 0.0936 0.125(5) 1.0000 Uiso R . . . . . 
H2213 H 0.9833 0.4055 -0.0290 0.125(5) 1.0000 Uiso R . . . . . 
H2221 H 0.7230 0.4986 0.1350 0.153(5) 1.0000 Uiso R . . . . . 
H2222 H 0.9061 0.5040 0.1313 0.153(5) 1.0000 Uiso R . . . . . 
H2223 H 0.7968 0.4911 0.0087 0.153(5) 1.0000 Uiso R . . . . . 
H2241 H 0.5982 0.4221 -0.0796 0.080(4) 1.0000 Uiso R . . . . . 
H2251 H 0.3722 0.3769 -0.1281 0.115(4) 1.0000 Uiso R . . . . . 
H2261 H 0.3032 0.3182 0.0025 0.105(4) 1.0000 Uiso R . . . . . 
H2271 H 0.4547 0.3045 0.1885 0.079(4) 1.0000 Uiso R . . . . . 
H2291 H 0.6425 0.3294 0.3344 0.046(6) 1.0000 Uiso R . . . . . 
H3111 H 1.1170 0.6297 0.6603 0.165(5) 1.0000 Uiso R . . . . . 
H3112 H 1.2633 0.6110 0.7486 0.165(5) 1.0000 Uiso R . . . . . 
H3113 H 1.1024 0.6210 0.8028 0.165(5) 1.0000 Uiso R . . . . . 
H3121 H 1.1187 0.4779 0.8090 0.155(5) 1.0000 Uiso R . . . . . 
H3122 H 1.2645 0.5119 0.8456 0.155(5) 1.0000 Uiso R . . . . . 
H3123 H 1.1035 0.5219 0.8999 0.155(5) 1.0000 Uiso R . . . . . 
H3141 H 0.8115 0.5456 0.8227 0.092(4) 1.0000 Uiso R . . . . . 
H3151 H 0.5492 0.5409 0.7586 0.101(4) 1.0000 Uiso R . . . . . 
H3161 H 0.4585 0.5301 0.5541 0.088(4) 1.0000 Uiso R . . . . . 
H3171 H 0.6380 0.5287 0.4081 0.073(4) 1.0000 Uiso R . . . . . 
H3191 H 0.8890 0.5144 0.3689 0.050(6) 1.0000 Uiso R . . . . . 
H3211 H 1.2843 0.6229 0.4809 0.159(5) 1.0000 Uiso R . . . . . 
H3212 H 1.1887 0.6635 0.4033 0.159(5) 1.0000 Uiso R . . . . . 
H3213 H 1.3346 0.6390 0.3509 0.159(5) 1.0000 Uiso R . . . . . 
H3221 H 0.9843 0.5846 0.1280 0.148(5) 1.0000 Uiso R . . . . . 
H3222 H 0.9936 0.6391 0.1713 0.148(5) 1.0000 Uiso R . . . . . 
H3223 H 1.1395 0.6146 0.1189 0.148(5) 1.0000 Uiso R . . . . . 
H3241 H 1.3309 0.5452 0.1611 0.093(4) 1.0000 Uiso R . . . . . 
H3251 H 1.4388 0.4687 0.1491 0.096(4) 1.0000 Uiso R . . . . . 
H3261 H 1.3858 0.4107 0.2864 0.091(4) 1.0000 Uiso R . . . . . 
H3271 H 1.2252 0.4268 0.4364 0.074(4) 1.0000 Uiso R . . . . . 
H3291 H 1.0534 0.4754 0.5193 0.048(6) 1.0000 Uiso R . . . . . 



loop_
 _geom_bond_atom_site_label_1
 _geom_bond_site_symmetry_1
 _geom_bond_atom_site_label_2
 _geom_bond_site_symmetry_2
 _geom_bond_distance
 _geom_bond_publ_flag
Si11 . O11 . 1.635(4)    yes
Si11 . C111 . 1.849(6)    yes
Si11 . C112 . 1.857(6)    yes
Si11 . C113 . 1.851(6)    yes
Si12 . O12 . 1.646(4)    yes
Si12 . C121 . 1.840(5)    yes
Si12 . C122 . 1.865(5)    yes
Si12 . C123 . 1.858(6)    yes
Si21 . O21 . 1.644(4)    yes
Si21 . C211 . 1.842(5)    yes
Si21 . C212 . 1.865(5)    yes
Si21 . C213 . 1.878(6)    yes
Si22 . O22 . 1.649(4)    yes
Si22 . C221 . 1.838(6)    yes
Si22 . C222 . 1.860(6)    yes
Si22 . C223 . 1.838(6)    yes
Si31 . O31 . 1.637(4)    yes
Si31 . C311 . 1.858(6)    yes
Si31 . C312 . 1.844(6)    yes
Si31 . C313 . 1.851(6)    yes
Si32 . O32 . 1.654(4)    yes
Si32 . C321 . 1.842(6)    yes
Si32 . C322 . 1.851(6)    yes
Si32 . C323 . 1.860(6)    yes
O11 . C129 . 1.424(5)    yes
O12 . C119 . 1.414(6)    yes
O21 . C229 . 1.428(6)    yes
O22 . C219 . 1.435(6)    yes
O31 . C329 . 1.432(6)    yes
O32 . C319 . 1.432(6)    yes
C111 . H1111 . 1.000    no
C111 . H1112 . 1.000    no
C111 . H1113 . 1.000    no
C112 . H1121 . 1.000    no
C112 . H1122 . 1.000    no
C112 . H1123 . 1.000    no
C113 . C114 . 1.403(7)    yes
C113 . C118 . 1.395(7)    yes
C114 . C115 . 1.378(8)    yes
C114 . H1141 . 1.000    no
C115 . C116 . 1.373(8)    yes
C115 . H1151 . 1.000    no
C116 . C117 . 1.380(7)    yes
C116 . H1161 . 1.000    no
C117 . C118 . 1.376(7)    yes
C117 . H1171 . 1.000    no
C118 . C119 . 1.506(7)    yes
C119 . C129 . 1.529(6)    yes
C119 . H1191 . 1.000    no
C121 . H1211 . 1.000    no
C121 . H1212 . 1.000    no
C121 . H1213 . 1.000    no
C122 . H1221 . 1.000    no
C122 . H1222 . 1.000    no
C122 . H1223 . 1.000    no
C123 . C124 . 1.405(7)    yes
C123 . C128 . 1.390(7)    yes
C124 . C125 . 1.379(8)    yes
C124 . H1241 . 1.000    no
C125 . C126 . 1.347(9)    yes
C125 . H1251 . 1.000    no
C126 . C127 . 1.375(8)    yes
C126 . H1261 . 1.000    no
C127 . C128 . 1.391(7)    yes
C127 . H1271 . 1.000    no
C128 . C129 . 1.511(7)    yes
C129 . H1291 . 1.000    no
C211 . H2111 . 1.000    no
C211 . H2112 . 1.000    no
C211 . H2113 . 1.000    no
C212 . H2121 . 1.000    no
C212 . H2122 . 1.000    no
C212 . H2123 . 1.000    no
C213 . C214 . 1.403(7)    yes
C213 . C218 . 1.390(6)    yes
C214 . C215 . 1.390(7)    yes
C214 . H2141 . 1.000    no
C215 . C216 . 1.382(7)    yes
C215 . H2151 . 1.000    no
C216 . C217 . 1.360(7)    yes
C216 . H2161 . 1.000    no
C217 . C218 . 1.398(7)    yes
C217 . H2171 . 1.000    no
C218 . C219 . 1.502(7)    yes
C219 . C229 . 1.523(6)    yes
C219 . H2191 . 1.000    no
C221 . H2211 . 1.000    no
C221 . H2212 . 1.000    no
C221 . H2213 . 1.000    no
C222 . H2221 . 1.000    no
C222 . H2222 . 1.000    no
C222 . H2223 . 1.000    no
C223 . C224 . 1.398(7)    yes
C223 . C228 . 1.400(7)    yes
C224 . C225 . 1.392(8)    yes
C224 . H2241 . 1.000    no
C225 . C226 . 1.356(9)    yes
C225 . H2251 . 1.000    no
C226 . C227 . 1.399(8)    yes
C226 . H2261 . 1.000    no
C227 . C228 . 1.394(7)    yes
C227 . H2271 . 1.000    no
C228 . C229 . 1.509(7)    yes
C229 . H2291 . 1.000    no
C311 . H3111 . 1.000    no
C311 . H3112 . 1.000    no
C311 . H3113 . 1.000    no
C312 . H3121 . 1.000    no
C312 . H3122 . 1.000    no
C312 . H3123 . 1.000    no
C313 . C314 . 1.396(7)    yes
C313 . C318 . 1.397(7)    yes
C314 . C315 . 1.372(8)    yes
C314 . H3141 . 1.000    no
C315 . C316 . 1.383(8)    yes
C315 . H3151 . 1.000    no
C316 . C317 . 1.380(8)    yes
C316 . H3161 . 1.000    no
C317 . C318 . 1.393(7)    yes
C317 . H3171 . 1.000    no
C318 . C319 . 1.517(7)    yes
C319 . C329 . 1.520(7)    yes
C319 . H3191 . 1.000    no
C321 . H3211 . 1.000    no
C321 . H3212 . 1.000    no
C321 . H3213 . 1.000    no
C322 . H3221 . 1.000    no
C322 . H3222 . 1.000    no
C322 . H3223 . 1.000    no
C323 . C324 . 1.405(7)    yes
C323 . C328 . 1.385(7)    yes
C324 . C325 . 1.391(8)    yes
C324 . H3241 . 1.000    no
C325 . C326 . 1.364(8)    yes
C325 . H3251 . 1.000    no
C326 . C327 . 1.364(8)    yes
C326 . H3261 . 1.000    no
C327 . C328 . 1.372(7)    yes
C327 . H3271 . 1.000    no
C328 . C329 . 1.505(7)    yes
C329 . H3291 . 1.000    no

loop_
 _geom_angle_atom_site_label_1
 _geom_angle_site_symmetry_1
 _geom_angle_atom_site_label_2
 _geom_angle_site_symmetry_2
 _geom_angle_atom_site_label_3
 _geom_angle_site_symmetry_3
 _geom_angle
 _geom_angle_publ_flag
O11 . Si11 . C111 . 108.1(3)    yes
O11 . Si11 . C112 . 110.4(3)    yes
C111 . Si11 . C112 . 109.9(3)    yes
O11 . Si11 . C113 . 104.4(3)    yes
C111 . Si11 . C113 . 112.7(3)    yes
C112 . Si11 . C113 . 111.1(3)    yes
O12 . Si12 . C121 . 110.6(3)    yes
O12 . Si12 . C122 . 109.4(3)    yes
C121 . Si12 . C122 . 109.3(3)    yes
O12 . Si12 . C123 . 103.7(3)    yes
C121 . Si12 . C123 . 112.6(3)    yes
C122 . Si12 . C123 . 111.1(3)    yes
O21 . Si21 . C211 . 109.0(3)    yes
O21 . Si21 . C212 . 109.2(3)    yes
C211 . Si21 . C212 . 111.0(3)    yes
O21 . Si21 . C213 . 104.2(3)    yes
C211 . Si21 . C213 . 113.4(3)    yes
C212 . Si21 . C213 . 109.7(3)    yes
O22 . Si22 . C221 . 110.0(2)    yes
O22 . Si22 . C222 . 108.9(2)    yes
C221 . Si22 . C222 . 109.1(3)    yes
O22 . Si22 . C223 . 104.6(3)    yes
C221 . Si22 . C223 . 112.0(3)    yes
C222 . Si22 . C223 . 112.1(3)    yes
O31 . Si31 . C311 . 107.9(3)    yes
O31 . Si31 . C312 . 110.2(3)    yes
C311 . Si31 . C312 . 109.7(3)    yes
O31 . Si31 . C313 . 104.7(3)    yes
C311 . Si31 . C313 . 112.9(3)    yes
C312 . Si31 . C313 . 111.3(3)    yes
O32 . Si32 . C321 . 109.8(3)    yes
O32 . Si32 . C322 . 110.6(3)    yes
C321 . Si32 . C322 . 110.1(3)    yes
O32 . Si32 . C323 . 103.9(3)    yes
C321 . Si32 . C323 . 113.0(3)    yes
C322 . Si32 . C323 . 109.3(3)    yes
Si11 . O11 . C129 . 121.1(3)    yes
Si12 . O12 . C119 . 124.6(3)    yes
Si21 . O21 . C229 . 123.4(4)    yes
Si22 . O22 . C219 . 122.5(3)    yes
Si31 . O31 . C329 . 121.1(3)    yes
Si32 . O32 . C319 . 123.4(3)    yes
Si11 . C111 . H1111 . 109.0    no
Si11 . C111 . H1112 . 108.4    no
H1111 . C111 . H1112 . 109.5    no
Si11 . C111 . H1113 . 111.0    no
H1111 . C111 . H1113 . 109.5    no
H1112 . C111 . H1113 . 109.5    no
Si11 . C112 . H1121 . 108.5    no
Si11 . C112 . H1122 . 109.5    no
H1121 . C112 . H1122 . 109.5    no
Si11 . C112 . H1123 . 110.4    no
H1121 . C112 . H1123 . 109.5    no
H1122 . C112 . H1123 . 109.5    no
Si11 . C113 . C114 . 121.9(6)    yes
Si11 . C113 . C118 . 119.7(5)    yes
C114 . C113 . C118 . 118.4(6)    yes
C113 . C114 . C115 . 120.5(7)    yes
C113 . C114 . H1141 . 120.0    no
C115 . C114 . H1141 . 119.5    no
C114 . C115 . C116 . 121.0(7)    yes
C114 . C115 . H1151 . 120.3    no
C116 . C115 . H1151 . 118.7    no
C115 . C116 . C117 . 118.5(7)    yes
C115 . C116 . H1161 . 120.3    no
C117 . C116 . H1161 . 121.2    no
C116 . C117 . C118 . 122.1(6)    yes
C116 . C117 . H1171 . 119.7    no
C118 . C117 . H1171 . 118.2    no
C113 . C118 . C117 . 119.5(6)    yes
C113 . C118 . C119 . 120.8(6)    yes
C117 . C118 . C119 . 119.7(6)    yes
C118 . C119 . O12 . 109.0(5)    yes
C118 . C119 . C129 . 112.6(5)    yes
O12 . C119 . C129 . 112.8(4)    yes
C118 . C119 . H1191 . 106.7    no
O12 . C119 . H1191 . 107.8    no
C129 . C119 . H1191 . 107.6    no
Si12 . C121 . H1211 . 110.0    no
Si12 . C121 . H1212 . 109.7    no
H1211 . C121 . H1212 . 109.5    no
Si12 . C121 . H1213 . 108.7    no
H1211 . C121 . H1213 . 109.5    no
H1212 . C121 . H1213 . 109.5    no
Si12 . C122 . H1221 . 107.7    no
Si12 . C122 . H1222 . 110.6    no
H1221 . C122 . H1222 . 109.5    no
Si12 . C122 . H1223 . 110.1    no
H1221 . C122 . H1223 . 109.5    no
H1222 . C122 . H1223 . 109.5    no
Si12 . C123 . C124 . 123.6(6)    yes
Si12 . C123 . C128 . 119.8(5)    yes
C124 . C123 . C128 . 116.6(6)    yes
C123 . C124 . C125 . 121.1(7)    yes
C123 . C124 . H1241 . 119.6    no
C125 . C124 . H1241 . 119.1    no
C124 . C125 . C126 . 120.9(8)    yes
C124 . C125 . H1251 . 118.7    no
C126 . C125 . H1251 . 120.4    no
C125 . C126 . C127 . 120.1(8)    yes
C125 . C126 . H1261 . 117.4    no
C127 . C126 . H1261 . 122.4    no
C126 . C127 . C128 . 119.7(7)    yes
C126 . C127 . H1271 . 120.5    no
C128 . C127 . H1271 . 119.7    no
C127 . C128 . C123 . 121.5(6)    yes
C127 . C128 . C129 . 119.9(6)    yes
C123 . C128 . C129 . 118.6(6)    yes
C119 . C129 . C128 . 112.6(5)    yes
C119 . C129 . O11 . 110.4(4)    yes
C128 . C129 . O11 . 108.5(4)    yes
C119 . C129 . H1291 . 109.0    no
C128 . C129 . H1291 . 107.7    no
O11 . C129 . H1291 . 108.5    no
Si21 . C211 . H2111 . 108.3    no
Si21 . C211 . H2112 . 109.4    no
H2111 . C211 . H2112 . 109.5    no
Si21 . C211 . H2113 . 110.7    no
H2111 . C211 . H2113 . 109.5    no
H2112 . C211 . H2113 . 109.5    no
Si21 . C212 . H2121 . 111.1    no
Si21 . C212 . H2122 . 108.7    no
H2121 . C212 . H2122 . 109.5    no
Si21 . C212 . H2123 . 108.7    no
H2121 . C212 . H2123 . 109.5    no
H2122 . C212 . H2123 . 109.5    no
Si21 . C213 . C214 . 121.5(5)    yes
Si21 . C213 . C218 . 119.5(5)    yes
C214 . C213 . C218 . 118.9(6)    yes
C213 . C214 . C215 . 120.8(6)    yes
C213 . C214 . H2141 . 119.3    no
C215 . C214 . H2141 . 119.9    no
C214 . C215 . C216 . 119.2(6)    yes
C214 . C215 . H2151 . 121.5    no
C216 . C215 . H2151 . 119.3    no
C215 . C216 . C217 . 120.6(6)    yes
C215 . C216 . H2161 . 120.1    no
C217 . C216 . H2161 . 119.3    no
C216 . C217 . C218 . 121.1(6)    yes
C216 . C217 . H2171 . 119.8    no
C218 . C217 . H2171 . 119.1    no
C217 . C218 . C213 . 119.3(5)    yes
C217 . C218 . C219 . 121.0(6)    yes
C213 . C218 . C219 . 119.7(5)    yes
C218 . C219 . O22 . 108.0(4)    yes
C218 . C219 . C229 . 113.7(5)    yes
O22 . C219 . C229 . 110.7(4)    yes
C218 . C219 . H2191 . 108.0    no
O22 . C219 . H2191 . 108.4    no
C229 . C219 . H2191 . 107.9    no
Si22 . C221 . H2211 . 109.7    no
Si22 . C221 . H2212 . 108.3    no
H2211 . C221 . H2212 . 109.5    no
Si22 . C221 . H2213 . 110.4    no
H2211 . C221 . H2213 . 109.5    no
H2212 . C221 . H2213 . 109.5    no
Si22 . C222 . H2221 . 109.2    no
Si22 . C222 . H2222 . 110.0    no
H2221 . C222 . H2222 . 109.5    no
Si22 . C222 . H2223 . 109.3    no
H2221 . C222 . H2223 . 109.5    no
H2222 . C222 . H2223 . 109.5    no
Si22 . C223 . C224 . 123.5(6)    yes
Si22 . C223 . C228 . 119.5(5)    yes
C224 . C223 . C228 . 117.0(6)    yes
C223 . C224 . C225 . 121.0(7)    yes
C223 . C224 . H2241 . 120.4    no
C225 . C224 . H2241 . 118.6    no
C224 . C225 . C226 . 121.3(8)    yes
C224 . C225 . H2251 . 121.6    no
C226 . C225 . H2251 . 117.1    no
C225 . C226 . C227 . 119.6(8)    yes
C225 . C226 . H2261 . 122.6    no
C227 . C226 . H2261 . 117.8    no
C226 . C227 . C228 . 119.3(7)    yes
C226 . C227 . H2271 . 121.2    no
C228 . C227 . H2271 . 119.6    no
C223 . C228 . C227 . 121.8(6)    yes
C223 . C228 . C229 . 119.2(6)    yes
C227 . C228 . C229 . 119.0(6)    yes
C219 . C229 . C228 . 112.6(5)    yes
C219 . C229 . O21 . 110.8(5)    yes
C228 . C229 . O21 . 109.7(5)    yes
C219 . C229 . H2291 . 108.4    no
C228 . C229 . H2291 . 108.1    no
O21 . C229 . H2291 . 107.1    no
Si31 . C311 . H3111 . 109.3    no
Si31 . C311 . H3112 . 109.7    no
H3111 . C311 . H3112 . 109.5    no
Si31 . C311 . H3113 . 109.3    no
H3111 . C311 . H3113 . 109.5    no
H3112 . C311 . H3113 . 109.5    no
Si31 . C312 . H3121 . 109.0    no
Si31 . C312 . H3122 . 109.9    no
H3121 . C312 . H3122 . 109.5    no
Si31 . C312 . H3123 . 109.5    no
H3121 . C312 . H3123 . 109.5    no
H3122 . C312 . H3123 . 109.5    no
Si31 . C313 . C314 . 123.5(6)    yes
Si31 . C313 . C318 . 119.3(5)    yes
C314 . C313 . C318 . 117.2(6)    yes
C313 . C314 . C315 . 121.1(7)    yes
C313 . C314 . H3141 . 118.0    no
C315 . C314 . H3141 . 120.9    no
C314 . C315 . C316 . 121.9(8)    yes
C314 . C315 . H3151 . 118.2    no
C316 . C315 . H3151 . 119.8    no
C315 . C316 . C317 . 117.8(8)    yes
C315 . C316 . H3161 . 118.7    no
C317 . C316 . H3161 . 123.4    no
C316 . C317 . C318 . 121.1(7)    yes
C316 . C317 . H3171 . 117.9    no
C318 . C317 . H3171 . 121.0    no
C313 . C318 . C317 . 120.9(6)    yes
C313 . C318 . C319 . 120.7(6)    yes
C317 . C318 . C319 . 118.3(7)    yes
C318 . C319 . O32 . 108.8(5)    yes
C318 . C319 . C329 . 112.4(5)    yes
O32 . C319 . C329 . 110.8(4)    yes
C318 . C319 . H3191 . 107.4    no
O32 . C319 . H3191 . 109.3    no
C329 . C319 . H3191 . 108.0    no
Si32 . C321 . H3211 . 110.3    no
Si32 . C321 . H3212 . 109.5    no
H3211 . C321 . H3212 . 109.5    no
Si32 . C321 . H3213 . 108.6    no
H3211 . C321 . H3213 . 109.5    no
H3212 . C321 . H3213 . 109.5    no
Si32 . C322 . H3221 . 108.0    no
Si32 . C322 . H3222 . 110.2    no
H3221 . C322 . H3222 . 109.5    no
Si32 . C322 . H3223 . 110.3    no
H3221 . C322 . H3223 . 109.5    no
H3222 . C322 . H3223 . 109.5    no
Si32 . C323 . C324 . 122.8(6)    yes
Si32 . C323 . C328 . 119.8(5)    yes
C324 . C323 . C328 . 117.2(6)    yes
C323 . C324 . C325 . 120.8(7)    yes
C323 . C324 . H3241 . 119.3    no
C325 . C324 . H3241 . 119.9    no
C324 . C325 . C326 . 119.7(7)    yes
C324 . C325 . H3251 . 120.5    no
C326 . C325 . H3251 . 119.8    no
C325 . C326 . C327 . 120.2(7)    yes
C325 . C326 . H3261 . 118.9    no
C327 . C326 . H3261 . 120.9    no
C326 . C327 . C328 . 120.7(7)    yes
C326 . C327 . H3271 . 118.8    no
C328 . C327 . H3271 . 120.5    no
C323 . C328 . C327 . 121.3(6)    yes
C323 . C328 . C329 . 118.9(6)    yes
C327 . C328 . C329 . 119.8(6)    yes
C319 . C329 . C328 . 113.1(5)    yes
C319 . C329 . O31 . 110.6(5)    yes
C328 . C329 . O31 . 108.5(4)    yes
C319 . C329 . H3291 . 108.3    no
C328 . C329 . H3291 . 109.0    no
O31 . C329 . H3291 . 107.2    no
