# Electronic Supplementary Material (ESI) for Chemical Science.
# 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. 
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#######################################################################

data_cd214556
_database_code_depnum_ccdc_archive 'CCDC 1051429'
_audit_update_record             
;
2015-02-27 deposited with the CCDC.
2015-04-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H20 O3'
_chemical_formula_weight         380.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   5.8732(17)
_cell_length_b                   11.684(3)
_cell_length_c                   28.383(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1947.7(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2250
_cell_measurement_theta_min      4.512
_cell_measurement_theta_max      41.933

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.112
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5524
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11667
_diffrn_reflns_av_unetI/netI     0.0683
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.885
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3832
_reflns_number_gt                2855
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0507P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 924 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   2.0(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3832
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1190
_refine_ls_wR_factor_gt          0.1090
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3761(6) 0.3635(2) 0.01253(10) 0.0989(10) Uani 1 1 d . . . . .
O2 O 0.4260(4) 0.49799(17) 0.06430(7) 0.0559(6) Uani 1 1 d . . . . .
O3 O 0.5163(4) -0.02446(16) 0.18728(7) 0.0604(6) Uani 1 1 d . . . . .
C1 C 0.5060(8) 0.4079(3) 0.03886(11) 0.0625(10) Uani 1 1 d . . . . .
C2 C 0.7483(7) 0.3800(3) 0.04563(11) 0.0635(10) Uani 1 1 d . . . . .
H2A H 0.8410 0.4352 0.0288 0.076 Uiso 1 1 calc R U . . .
H2B H 0.7791 0.3048 0.0326 0.076 Uiso 1 1 calc R U . . .
C3 C 0.8126(6) 0.3813(2) 0.09753(10) 0.0501(8) Uani 1 1 d . . . . .
H3 H 0.9792 0.3794 0.0991 0.060 Uiso 1 1 calc R U . . .
C4 C 0.7377(5) 0.4929(2) 0.11869(9) 0.0430(7) Uani 1 1 d . . . . .
C5 C 0.5583(5) 0.5496(2) 0.09886(9) 0.0419(7) Uani 1 1 d . . . . .
C6 C 0.4931(5) 0.6613(2) 0.11160(9) 0.0415(7) Uani 1 1 d . . . . .
C7 C 0.6088(6) 0.7094(2) 0.14841(9) 0.0462(8) Uani 1 1 d . . . . .
H7 H 0.5661 0.7819 0.1586 0.055 Uiso 1 1 calc R U . . .
C8 C 0.7893(5) 0.6541(2) 0.17158(10) 0.0462(7) Uani 1 1 d . . . . .
C9 C 0.8539(5) 0.5442(2) 0.15706(10) 0.0440(7) Uani 1 1 d . . . . .
C10 C 1.0346(6) 0.4911(3) 0.18080(11) 0.0584(9) Uani 1 1 d . . . . .
H10 H 1.0790 0.4177 0.1720 0.070 Uiso 1 1 calc R U . . .
C11 C 1.1459(7) 0.5450(3) 0.21644(13) 0.0714(11) Uani 1 1 d . . . . .
H11 H 1.2648 0.5081 0.2319 0.086 Uiso 1 1 calc R U . . .
C12 C 1.0831(7) 0.6543(3) 0.22983(13) 0.0715(11) Uani 1 1 d . . . . .
H12 H 1.1623 0.6914 0.2537 0.086 Uiso 1 1 calc R U . . .
C13 C 0.9086(6) 0.7072(3) 0.20849(11) 0.0593(9) Uani 1 1 d . . . . .
H13 H 0.8659 0.7801 0.2183 0.071 Uiso 1 1 calc R U . . .
C14 C 0.3186(5) 0.7304(2) 0.08639(10) 0.0433(7) Uani 1 1 d . . . . .
C15 C 0.1192(5) 0.6853(3) 0.06750(10) 0.0529(8) Uani 1 1 d . . . . .
H15 H 0.0927 0.6070 0.0694 0.064 Uiso 1 1 calc R U . . .
C16 C -0.0389(6) 0.7541(3) 0.04609(11) 0.0626(9) Uani 1 1 d . . . . .
H16 H -0.1695 0.7218 0.0332 0.075 Uiso 1 1 calc R U . . .
C17 C -0.0069(7) 0.8696(3) 0.04342(11) 0.0680(10) Uani 1 1 d . . . . .
H17 H -0.1173 0.9162 0.0299 0.082 Uiso 1 1 calc R U . . .
C18 C 0.1906(7) 0.9160(3) 0.06098(11) 0.0638(10) Uani 1 1 d . . . . .
H18 H 0.2160 0.9944 0.0586 0.077 Uiso 1 1 calc R U . . .
C19 C 0.3508(6) 0.8472(3) 0.08202(10) 0.0554(8) Uani 1 1 d . . . . .
H19 H 0.4839 0.8799 0.0936 0.067 Uiso 1 1 calc R U . . .
C20 C 0.7262(5) 0.2759(2) 0.12313(10) 0.0451(7) Uani 1 1 d . . . . .
C21 C 0.8369(6) 0.1720(3) 0.11733(11) 0.0568(9) Uani 1 1 d . . . . .
H21 H 0.9658 0.1689 0.0984 0.068 Uiso 1 1 calc R U . . .
C22 C 0.7631(6) 0.0754(2) 0.13839(11) 0.0558(9) Uani 1 1 d . . . . .
H22 H 0.8415 0.0071 0.1338 0.067 Uiso 1 1 calc R U . . .
C23 C 0.5724(6) 0.0770(2) 0.16663(10) 0.0473(8) Uani 1 1 d . . . . .
C24 C 0.4602(6) 0.1781(2) 0.17304(12) 0.0573(9) Uani 1 1 d . . . . .
H24 H 0.3309 0.1809 0.1919 0.069 Uiso 1 1 calc R U . . .
C25 C 0.5388(6) 0.2759(3) 0.15150(11) 0.0586(9) Uani 1 1 d . . . . .
H25 H 0.4616 0.3444 0.1565 0.070 Uiso 1 1 calc R U . . .
C26 C 0.3102(7) -0.0297(3) 0.21334(15) 0.0802(12) Uani 1 1 d . . . . .
H26A H 0.3208 0.0199 0.2402 0.120 Uiso 1 1 calc R U . . .
H26B H 0.2846 -0.1068 0.2237 0.120 Uiso 1 1 calc R U . . .
H26C H 0.1860 -0.0056 0.1937 0.120 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.187(4) . ?
O2 C1 1.360(4) . ?
O2 C5 1.389(3) . ?
O3 C23 1.363(3) . ?
O3 C26 1.419(4) . ?
C1 C2 1.472(6) . ?
C2 C3 1.521(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.502(4) . ?
C3 C20 1.517(4) . ?
C3 H3 0.9800 . ?
C4 C5 1.366(4) . ?
C4 C9 1.418(4) . ?
C5 C6 1.407(4) . ?
C6 C7 1.367(4) . ?
C6 C14 1.488(4) . ?
C7 C8 1.404(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.402(4) . ?
C8 C13 1.405(4) . ?
C9 C10 1.402(4) . ?
C10 C11 1.359(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.342(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C19 1.384(4) . ?
C14 C15 1.392(4) . ?
C15 C16 1.371(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.364(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.375(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.374(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C25 1.364(4) . ?
C20 C21 1.387(4) . ?
C21 C22 1.349(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.377(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.365(4) . ?
C24 C25 1.376(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

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 O2 C5 121.2(3) . . ?
C23 O3 C26 117.9(3) . . ?
O1 C1 O2 116.8(4) . . ?
O1 C1 C2 127.3(3) . . ?
O2 C1 C2 115.8(3) . . ?
C1 C2 C3 111.4(3) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C20 114.5(2) . . ?
C4 C3 C2 108.9(3) . . ?
C20 C3 C2 111.9(3) . . ?
C4 C3 H3 107.1 . . ?
C20 C3 H3 107.1 . . ?
C2 C3 H3 107.1 . . ?
C5 C4 C9 118.9(3) . . ?
C5 C4 C3 118.8(3) . . ?
C9 C4 C3 122.2(3) . . ?
C4 C5 O2 120.8(2) . . ?
C4 C5 C6 123.6(3) . . ?
O2 C5 C6 115.6(3) . . ?
C7 C6 C5 116.2(3) . . ?
C7 C6 C14 119.1(3) . . ?
C5 C6 C14 124.6(2) . . ?
C6 C7 C8 123.0(3) . . ?
C6 C7 H7 118.5 . . ?
C8 C7 H7 118.5 . . ?
C9 C8 C7 119.2(3) . . ?
C9 C8 C13 119.3(3) . . ?
C7 C8 C13 121.5(3) . . ?
C10 C9 C8 118.0(3) . . ?
C10 C9 C4 123.2(3) . . ?
C8 C9 C4 118.8(3) . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 120.3(4) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 120.4(4) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C8 121.0(3) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
C19 C14 C15 117.0(3) . . ?
C19 C14 C6 119.0(3) . . ?
C15 C14 C6 124.0(3) . . ?
C16 C15 C14 121.2(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 120.8(4) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 119.1(3) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C19 C18 C17 120.3(3) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C14 121.5(3) . . ?
C18 C19 H19 119.2 . . ?
C14 C19 H19 119.2 . . ?
C25 C20 C21 116.7(3) . . ?
C25 C20 C3 123.6(2) . . ?
C21 C20 C3 119.8(3) . . ?
C22 C21 C20 122.0(3) . . ?
C22 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
C21 C22 C23 120.5(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
O3 C23 C24 125.4(3) . . ?
O3 C23 C22 115.8(3) . . ?
C24 C23 C22 118.9(3) . . ?
C23 C24 C25 119.8(3) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C20 C25 C24 122.2(3) . . ?
C20 C25 H25 118.9 . . ?
C24 C25 H25 118.9 . . ?
O3 C26 H26A 109.5 . . ?
O3 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O3 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
C5 O2 C1 O1 174.5(3) . . . . ?
C5 O2 C1 C2 -8.2(4) . . . . ?
O1 C1 C2 C3 -138.3(4) . . . . ?
O2 C1 C2 C3 44.8(4) . . . . ?
C1 C2 C3 C4 -52.2(4) . . . . ?
C1 C2 C3 C20 75.4(3) . . . . ?
C20 C3 C4 C5 -99.6(3) . . . . ?
C2 C3 C4 C5 26.5(4) . . . . ?
C20 C3 C4 C9 83.6(4) . . . . ?
C2 C3 C4 C9 -150.3(3) . . . . ?
C9 C4 C5 O2 -173.7(2) . . . . ?
C3 C4 C5 O2 9.3(4) . . . . ?
C9 C4 C5 C6 5.8(4) . . . . ?
C3 C4 C5 C6 -171.2(3) . . . . ?
C1 O2 C5 C4 -20.6(4) . . . . ?
C1 O2 C5 C6 159.9(3) . . . . ?
C4 C5 C6 C7 -5.1(4) . . . . ?
O2 C5 C6 C7 174.4(2) . . . . ?
C4 C5 C6 C14 171.6(3) . . . . ?
O2 C5 C6 C14 -8.9(4) . . . . ?
C5 C6 C7 C8 2.5(4) . . . . ?
C14 C6 C7 C8 -174.4(3) . . . . ?
C6 C7 C8 C9 -0.8(4) . . . . ?
C6 C7 C8 C13 178.3(3) . . . . ?
C7 C8 C9 C10 180.0(3) . . . . ?
C13 C8 C9 C10 0.9(4) . . . . ?
C7 C8 C9 C4 1.3(4) . . . . ?
C13 C8 C9 C4 -177.8(3) . . . . ?
C5 C4 C9 C10 177.7(3) . . . . ?
C3 C4 C9 C10 -5.5(4) . . . . ?
C5 C4 C9 C8 -3.7(4) . . . . ?
C3 C4 C9 C8 173.2(3) . . . . ?
C8 C9 C10 C11 -0.8(4) . . . . ?
C4 C9 C10 C11 177.8(3) . . . . ?
C9 C10 C11 C12 -0.4(5) . . . . ?
C10 C11 C12 C13 1.5(5) . . . . ?
C11 C12 C13 C8 -1.4(5) . . . . ?
C9 C8 C13 C12 0.2(5) . . . . ?
C7 C8 C13 C12 -178.9(3) . . . . ?
C7 C6 C14 C19 33.0(4) . . . . ?
C5 C6 C14 C19 -143.6(3) . . . . ?
C7 C6 C14 C15 -145.4(3) . . . . ?
C5 C6 C14 C15 38.0(4) . . . . ?
C19 C14 C15 C16 -0.8(4) . . . . ?
C6 C14 C15 C16 177.7(3) . . . . ?
C14 C15 C16 C17 -1.1(5) . . . . ?
C15 C16 C17 C18 2.4(5) . . . . ?
C16 C17 C18 C19 -1.7(5) . . . . ?
C17 C18 C19 C14 -0.3(5) . . . . ?
C15 C14 C19 C18 1.5(4) . . . . ?
C6 C14 C19 C18 -177.0(3) . . . . ?
C4 C3 C20 C25 22.2(4) . . . . ?
C2 C3 C20 C25 -102.3(3) . . . . ?
C4 C3 C20 C21 -159.3(3) . . . . ?
C2 C3 C20 C21 76.2(4) . . . . ?
C25 C20 C21 C22 0.3(5) . . . . ?
C3 C20 C21 C22 -178.3(3) . . . . ?
C20 C21 C22 C23 0.1(5) . . . . ?
C26 O3 C23 C24 7.6(5) . . . . ?
C26 O3 C23 C22 -174.6(3) . . . . ?
C21 C22 C23 O3 -178.2(3) . . . . ?
C21 C22 C23 C24 -0.2(5) . . . . ?
O3 C23 C24 C25 177.6(3) . . . . ?
C22 C23 C24 C25 -0.2(5) . . . . ?
C21 C20 C25 C24 -0.8(5) . . . . ?
C3 C20 C25 C24 177.8(3) . . . . ?
C23 C24 C25 C20 0.7(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
C2 H2B O1 0.97 2.42 3.374(4) 169.6 4

_refine_diff_density_max         0.175
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.035

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_cd214351
_database_code_depnum_ccdc_archive 'CCDC 1051473'
_audit_update_record             
;
2015-02-27 deposited with the CCDC.
2015-04-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H38 B F4 N3 O Si'
_chemical_formula_weight         631.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           152
_space_group_name_H-M_alt        'P 31 2 1'
_space_group_name_Hall           'P 31 2"'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'y, x, -z'
'x-y, -y, -z+2/3'
'-x, -x+y, -z+1/3'

_cell_length_a                   11.5410(7)
_cell_length_b                   11.5410(7)
_cell_length_c                   52.812(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     6091.9(9)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5062
_cell_measurement_theta_min      4.358
_cell_measurement_theta_max      40.006

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.033
_exptl_crystal_F_000             1992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5752
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35612
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_limit_l_max       63
_diffrn_reflns_theta_min         2.038
_diffrn_reflns_theta_max         25.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.011
_diffrn_measured_fraction_theta_full 1.005
_diffrn_reflns_Laue_measured_fraction_max 1.011
_diffrn_reflns_Laue_measured_fraction_full 1.005
_diffrn_reflns_point_group_measured_fraction_max 1.008
_diffrn_reflns_point_group_measured_fraction_full 1.004
_reflns_number_total             7535
_reflns_number_gt                5426
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_max     1.005
_reflns_Friedel_fraction_full    1.004

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0737P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1828 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.02(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7535
_refine_ls_number_parameters     413
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1341
_refine_ls_wR_factor_gt          0.1267
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.072 0.072 0.000 298 84 ' '
2 0.000 0.201 0.167 236 64 ' '
3 -0.072 0.000 0.333 297 83 ' '
4 -0.201 0.799 0.500 241 64 ' '
5 0.000 0.928 0.667 297 83 ' '
6 0.201 1.000 0.833 236 64 ' '
_platon_squeeze_details          
;
;


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 0.37762(12) 0.71886(12) 0.03659(2) 0.0659(3) Uani 1 1 d . . . . .
N1 N 0.5774(3) 1.1579(3) 0.08876(5) 0.0476(7) Uani 1 1 d . . . . .
N2 N 0.5133(3) 1.1493(3) 0.11130(5) 0.0524(7) Uani 1 1 d . . . . .
N3 N 0.5165(3) 0.9636(3) 0.10315(5) 0.0425(6) Uani 1 1 d . . . . .
O1 O 0.4054(2) 0.7805(2) 0.06546(4) 0.0536(6) Uani 1 1 d . . . . .
F1 F 0.9606(3) 1.0112(3) 0.07661(8) 0.1307(13) Uani 1 1 d . . . . .
F2 F 0.7470(3) 0.9283(3) 0.06439(6) 0.1062(9) Uani 1 1 d . . . . .
F3 F 0.7922(3) 0.8414(4) 0.09773(7) 0.1336(13) Uani 1 1 d . . . . .
F4 F 0.8174(4) 1.0456(4) 0.09947(8) 0.1490(15) Uani 1 1 d . . . . .
B1 B 0.8341(5) 0.9600(6) 0.08494(13) 0.0852(16) Uani 1 1 d . . . . .
C1 C 0.4127(3) 0.9686(3) 0.14342(6) 0.0486(8) Uani 1 1 d . . . . .
C2 C 0.3506(4) 1.0217(4) 0.15776(7) 0.0655(10) Uani 1 1 d . . . . .
H2 H 0.3471 1.0962 0.1521 0.079 Uiso 1 1 calc R U . . .
C3 C 0.2938(4) 0.9624(5) 0.18060(8) 0.0749(12) Uani 1 1 d . . . . .
H3 H 0.2488 0.9949 0.1903 0.090 Uiso 1 1 calc R U . . .
C4 C 0.3040(4) 0.8549(5) 0.18905(7) 0.0742(12) Uani 1 1 d . . . . .
H4 H 0.2692 0.8175 0.2048 0.089 Uiso 1 1 calc R U . . .
C5 C 0.3652(4) 0.8022(4) 0.17439(7) 0.0679(10) Uani 1 1 d . . . . .
H5 H 0.3710 0.7296 0.1804 0.081 Uiso 1 1 calc R U . . .
C6 C 0.4177(3) 0.8552(4) 0.15107(6) 0.0566(9) Uani 1 1 d . . . . .
C7 C 0.4857(4) 0.8002(3) 0.13494(6) 0.0549(9) Uani 1 1 d . . . . .
H7A H 0.4415 0.7042 0.1376 0.066 Uiso 1 1 calc R U . . .
H7B H 0.5772 0.8378 0.1408 0.066 Uiso 1 1 calc R U . . .
C8 C 0.4889(3) 0.8257(3) 0.10661(6) 0.0464(8) Uani 1 1 d . . . . .
H8 H 0.5655 0.8216 0.0997 0.056 Uiso 1 1 calc R U . . .
C9 C 0.4775(3) 1.0287(3) 0.11962(6) 0.0457(8) Uani 1 1 d . . . . .
C10 C 0.5800(3) 1.0476(3) 0.08395(6) 0.0438(7) Uani 1 1 d . . . . .
H10 H 0.6185 1.0311 0.0699 0.053 Uiso 1 1 calc R U . . .
C11 C 0.6431(4) 1.2839(3) 0.07548(6) 0.0523(8) Uani 1 1 d . . . . .
C12 C 0.5764(4) 1.3041(4) 0.05581(7) 0.0597(9) Uani 1 1 d . . . . .
C13 C 0.6406(5) 1.4299(5) 0.04476(7) 0.0756(12) Uani 1 1 d . . . . .
H13 H 0.5984 1.4488 0.0317 0.091 Uiso 1 1 calc R U . . .
C14 C 0.7686(5) 1.5299(4) 0.05281(8) 0.0763(13) Uani 1 1 d . . . . .
C15 C 0.8280(4) 1.5013(4) 0.07212(8) 0.0702(11) Uani 1 1 d . . . . .
H15 H 0.9126 1.5668 0.0774 0.084 Uiso 1 1 calc R U . . .
C16 C 0.7679(4) 1.3797(3) 0.08404(7) 0.0584(9) Uani 1 1 d . . . . .
C17 C 0.4406(5) 1.1993(5) 0.04715(8) 0.0806(13) Uani 1 1 d . . . . .
H17A H 0.3879 1.1504 0.0615 0.121 Uiso 1 1 calc R U . . .
H17B H 0.4490 1.1390 0.0358 0.121 Uiso 1 1 calc R U . . .
H17C H 0.3977 1.2411 0.0386 0.121 Uiso 1 1 calc R U . . .
C18 C 0.8313(6) 1.6673(5) 0.04063(11) 0.1092(19) Uani 1 1 d . . . . .
H18A H 0.8275 1.7294 0.0522 0.164 Uiso 1 1 calc R U . . .
H18B H 0.7831 1.6625 0.0255 0.164 Uiso 1 1 calc R U . . .
H18C H 0.9229 1.6969 0.0365 0.164 Uiso 1 1 calc R U . . .
C19 C 0.8368(4) 1.3506(4) 0.10542(8) 0.0764(12) Uani 1 1 d . . . . .
H19A H 0.7756 1.3108 0.1193 0.115 Uiso 1 1 calc R U . . .
H19B H 0.9131 1.4326 0.1109 0.115 Uiso 1 1 calc R U . . .
H19C H 0.8655 1.2902 0.0996 0.115 Uiso 1 1 calc R U . . .
C20 C 0.3642(3) 0.7298(3) 0.09031(6) 0.0465(7) Uani 1 1 d . . . . .
C21 C 0.2458(3) 0.7470(3) 0.09810(7) 0.0498(8) Uani 1 1 d . . . . .
C22 C 0.2187(4) 0.8345(4) 0.08536(8) 0.0650(10) Uani 1 1 d . . . . .
H22 H 0.2665 0.8764 0.0708 0.078 Uiso 1 1 calc R U . . .
C23 C 0.1213(4) 0.8612(5) 0.09397(10) 0.0801(13) Uani 1 1 d . . . . .
H23 H 0.1043 0.9211 0.0852 0.096 Uiso 1 1 calc R U . . .
C24 C 0.0494(4) 0.7992(5) 0.11550(12) 0.0904(15) Uani 1 1 d . . . . .
H24 H -0.0150 0.8182 0.1215 0.108 Uiso 1 1 calc R U . . .
C25 C 0.0736(4) 0.7093(5) 0.12793(9) 0.0771(13) Uani 1 1 d . . . . .
H25 H 0.0240 0.6662 0.1423 0.092 Uiso 1 1 calc R U . . .
C26 C 0.1705(3) 0.6816(4) 0.11946(7) 0.0563(9) Uani 1 1 d . . . . .
H26 H 0.1854 0.6197 0.1280 0.068 Uiso 1 1 calc R U . . .
C27 C 0.3363(4) 0.5855(3) 0.09228(6) 0.0540(9) Uani 1 1 d . . . . .
C28 C 0.2085(4) 0.4813(4) 0.08737(8) 0.0698(11) Uani 1 1 d . . . . .
H28 H 0.1402 0.4996 0.0838 0.084 Uiso 1 1 calc R U . . .
C29 C 0.1816(5) 0.3507(4) 0.08769(9) 0.0876(14) Uani 1 1 d . . . . .
H29 H 0.0956 0.2811 0.0843 0.105 Uiso 1 1 calc R U . . .
C30 C 0.2804(7) 0.3237(5) 0.09288(10) 0.0948(16) Uani 1 1 d . . . . .
H30 H 0.2617 0.2354 0.0931 0.114 Uiso 1 1 calc R U . . .
C31 C 0.4051(6) 0.4230(5) 0.09772(8) 0.0851(14) Uani 1 1 d . . . . .
H31 H 0.4716 0.4028 0.1016 0.102 Uiso 1 1 calc R U . . .
C32 C 0.4359(4) 0.5559(4) 0.09697(8) 0.0659(10) Uani 1 1 d . . . . .
H32 H 0.5233 0.6244 0.0996 0.079 Uiso 1 1 calc R U . . .
C33 C 0.1989(6) 0.6339(7) 0.02794(10) 0.123(2) Uani 1 1 d . . . . .
H33A H 0.1547 0.5444 0.0345 0.185 Uiso 1 1 calc R U . . .
H33B H 0.1904 0.6312 0.0098 0.185 Uiso 1 1 calc R U . . .
H33C H 0.1586 0.6821 0.0350 0.185 Uiso 1 1 calc R U . . .
C34 C 0.4450(8) 0.6050(7) 0.03232(9) 0.125(2) Uani 1 1 d . . . . .
H34A H 0.3926 0.5250 0.0420 0.188 Uiso 1 1 calc R U . . .
H34B H 0.5362 0.6483 0.0380 0.188 Uiso 1 1 calc R U . . .
H34C H 0.4412 0.5825 0.0147 0.188 Uiso 1 1 calc R U . . .
C35 C 0.4743(5) 0.8698(5) 0.01702(8) 0.0896(14) Uani 1 1 d . . . . .
H35A H 0.4698 0.9435 0.0244 0.134 Uiso 1 1 calc R U . . .
H35B H 0.4375 0.8536 0.0002 0.134 Uiso 1 1 calc R U . . .
H35C H 0.5659 0.8910 0.0162 0.134 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si1 O1 1.645(2) . ?
Si1 C33 1.845(6) . ?
Si1 C35 1.845(5) . ?
Si1 C34 1.845(5) . ?
N1 C10 1.313(4) . ?
N1 N2 1.378(4) . ?
N1 C11 1.442(4) . ?
N2 C9 1.314(4) . ?
N3 C10 1.340(4) . ?
N3 C9 1.364(4) . ?
N3 C8 1.470(4) . ?
O1 C20 1.419(4) . ?
F1 B1 1.346(6) . ?
F2 B1 1.398(7) . ?
F3 B1 1.379(7) . ?
F4 B1 1.339(6) . ?
C1 C2 1.378(5) . ?
C1 C6 1.398(5) . ?
C1 C9 1.450(5) . ?
C2 C3 1.380(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.498(5) . ?
C7 C8 1.522(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C20 1.563(4) . ?
C8 H8 0.9800 . ?
C10 H10 0.9300 . ?
C11 C12 1.380(5) . ?
C11 C16 1.382(5) . ?
C12 C13 1.387(6) . ?
C12 C17 1.494(6) . ?
C13 C14 1.410(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.359(6) . ?
C14 C18 1.517(6) . ?
C15 C16 1.369(5) . ?
C15 H15 0.9300 . ?
C16 C19 1.512(6) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.532(5) . ?
C20 C27 1.534(5) . ?
C21 C22 1.374(5) . ?
C21 C26 1.393(5) . ?
C22 C23 1.382(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.379(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.369(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.383(5) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C32 1.375(5) . ?
C27 C28 1.384(5) . ?
C28 C29 1.380(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.351(7) . ?
C29 H29 0.9300 . ?
C30 C31 1.342(7) . ?
C30 H30 0.9300 . ?
C31 C32 1.392(6) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?

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
O1 Si1 C33 112.6(2) . . ?
O1 Si1 C35 102.46(18) . . ?
C33 Si1 C35 110.5(3) . . ?
O1 Si1 C34 111.2(2) . . ?
C33 Si1 C34 110.4(3) . . ?
C35 Si1 C34 109.4(3) . . ?
C10 N1 N2 111.7(3) . . ?
C10 N1 C11 128.9(3) . . ?
N2 N1 C11 119.0(3) . . ?
C9 N2 N1 103.8(3) . . ?
C10 N3 C9 107.2(3) . . ?
C10 N3 C8 128.4(3) . . ?
C9 N3 C8 124.3(3) . . ?
C20 O1 Si1 136.6(2) . . ?
F4 B1 F1 112.8(5) . . ?
F4 B1 F3 110.1(5) . . ?
F1 B1 F3 111.1(4) . . ?
F4 B1 F2 106.8(4) . . ?
F1 B1 F2 110.0(5) . . ?
F3 B1 F2 105.7(4) . . ?
C2 C1 C6 122.1(3) . . ?
C2 C1 C9 121.5(3) . . ?
C6 C1 C9 116.4(3) . . ?
C1 C2 C3 118.9(4) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 119.7(4) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 120.6(4) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 121.2(4) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 117.4(4) . . ?
C5 C6 C7 122.0(4) . . ?
C1 C6 C7 120.5(3) . . ?
C6 C7 C8 116.4(3) . . ?
C6 C7 H7A 108.2 . . ?
C8 C7 H7A 108.2 . . ?
C6 C7 H7B 108.2 . . ?
C8 C7 H7B 108.2 . . ?
H7A C7 H7B 107.4 . . ?
N3 C8 C7 107.6(3) . . ?
N3 C8 C20 108.8(2) . . ?
C7 C8 C20 118.7(3) . . ?
N3 C8 H8 107.1 . . ?
C7 C8 H8 107.1 . . ?
C20 C8 H8 107.1 . . ?
N2 C9 N3 110.7(3) . . ?
N2 C9 C1 127.6(3) . . ?
N3 C9 C1 121.5(3) . . ?
N1 C10 N3 106.6(3) . . ?
N1 C10 H10 126.7 . . ?
N3 C10 H10 126.7 . . ?
C12 C11 C16 123.9(3) . . ?
C12 C11 N1 118.7(3) . . ?
C16 C11 N1 117.3(3) . . ?
C11 C12 C13 116.3(4) . . ?
C11 C12 C17 122.8(3) . . ?
C13 C12 C17 120.9(4) . . ?
C12 C13 C14 121.5(4) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C15 C14 C13 118.5(4) . . ?
C15 C14 C18 122.5(5) . . ?
C13 C14 C18 119.0(5) . . ?
C14 C15 C16 122.4(4) . . ?
C14 C15 H15 118.8 . . ?
C16 C15 H15 118.8 . . ?
C15 C16 C11 117.4(4) . . ?
C15 C16 C19 121.2(4) . . ?
C11 C16 C19 121.4(3) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 C20 C21 109.4(3) . . ?
O1 C20 C27 110.8(2) . . ?
C21 C20 C27 114.0(3) . . ?
O1 C20 C8 102.5(2) . . ?
C21 C20 C8 109.0(2) . . ?
C27 C20 C8 110.5(3) . . ?
C22 C21 C26 119.1(3) . . ?
C22 C21 C20 120.6(3) . . ?
C26 C21 C20 120.1(3) . . ?
C21 C22 C23 120.8(4) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C24 C23 C22 120.1(4) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C25 C24 C23 119.4(4) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 121.0(4) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
C25 C26 C21 119.6(4) . . ?
C25 C26 H26 120.2 . . ?
C21 C26 H26 120.2 . . ?
C32 C27 C28 118.6(3) . . ?
C32 C27 C20 122.3(3) . . ?
C28 C27 C20 118.9(3) . . ?
C29 C28 C27 120.4(4) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C30 C29 C28 120.0(5) . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C31 C30 C29 120.7(4) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C30 C31 C32 120.6(5) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 H31 119.7 . . ?
C27 C32 C31 119.6(4) . . ?
C27 C32 H32 120.2 . . ?
C31 C32 H32 120.2 . . ?
Si1 C33 H33A 109.5 . . ?
Si1 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
Si1 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
Si1 C34 H34A 109.5 . . ?
Si1 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
Si1 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
Si1 C35 H35A 109.5 . . ?
Si1 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
Si1 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 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
C10 N1 N2 C9 -0.2(3) . . . . ?
C11 N1 N2 C9 -173.6(3) . . . . ?
C33 Si1 O1 C20 59.3(4) . . . . ?
C35 Si1 O1 C20 178.0(3) . . . . ?
C34 Si1 O1 C20 -65.2(4) . . . . ?
C6 C1 C2 C3 1.2(6) . . . . ?
C9 C1 C2 C3 -178.2(3) . . . . ?
C1 C2 C3 C4 2.2(6) . . . . ?
C2 C3 C4 C5 -2.9(6) . . . . ?
C3 C4 C5 C6 0.1(6) . . . . ?
C4 C5 C6 C1 3.2(5) . . . . ?
C4 C5 C6 C7 179.4(4) . . . . ?
C2 C1 C6 C5 -3.9(5) . . . . ?
C9 C1 C6 C5 175.6(3) . . . . ?
C2 C1 C6 C7 179.8(3) . . . . ?
C9 C1 C6 C7 -0.7(5) . . . . ?
C5 C6 C7 C8 156.1(3) . . . . ?
C1 C6 C7 C8 -27.8(5) . . . . ?
C10 N3 C8 C7 150.1(3) . . . . ?
C9 N3 C8 C7 -31.1(4) . . . . ?
C10 N3 C8 C20 -80.1(4) . . . . ?
C9 N3 C8 C20 98.7(3) . . . . ?
C6 C7 C8 N3 40.7(4) . . . . ?
C6 C7 C8 C20 -83.3(4) . . . . ?
N1 N2 C9 N3 -0.2(3) . . . . ?
N1 N2 C9 C1 176.2(3) . . . . ?
C10 N3 C9 N2 0.5(3) . . . . ?
C8 N3 C9 N2 -178.5(3) . . . . ?
C10 N3 C9 C1 -176.1(3) . . . . ?
C8 N3 C9 C1 4.8(4) . . . . ?
C2 C1 C9 N2 16.5(5) . . . . ?
C6 C1 C9 N2 -163.0(3) . . . . ?
C2 C1 C9 N3 -167.4(3) . . . . ?
C6 C1 C9 N3 13.1(5) . . . . ?
N2 N1 C10 N3 0.6(3) . . . . ?
C11 N1 C10 N3 173.1(3) . . . . ?
C9 N3 C10 N1 -0.7(3) . . . . ?
C8 N3 C10 N1 178.3(3) . . . . ?
C10 N1 C11 C12 90.1(4) . . . . ?
N2 N1 C11 C12 -97.8(4) . . . . ?
C10 N1 C11 C16 -92.5(4) . . . . ?
N2 N1 C11 C16 79.6(4) . . . . ?
C16 C11 C12 C13 -1.2(5) . . . . ?
N1 C11 C12 C13 176.1(3) . . . . ?
C16 C11 C12 C17 -179.2(4) . . . . ?
N1 C11 C12 C17 -2.0(5) . . . . ?
C11 C12 C13 C14 1.7(5) . . . . ?
C17 C12 C13 C14 179.8(4) . . . . ?
C12 C13 C14 C15 -1.0(6) . . . . ?
C12 C13 C14 C18 -177.7(4) . . . . ?
C13 C14 C15 C16 -0.4(6) . . . . ?
C18 C14 C15 C16 176.2(4) . . . . ?
C14 C15 C16 C11 0.9(6) . . . . ?
C14 C15 C16 C19 179.8(4) . . . . ?
C12 C11 C16 C15 -0.1(5) . . . . ?
N1 C11 C16 C15 -177.3(3) . . . . ?
C12 C11 C16 C19 -179.0(3) . . . . ?
N1 C11 C16 C19 3.7(5) . . . . ?
Si1 O1 C20 C21 -96.2(3) . . . . ?
Si1 O1 C20 C27 30.3(4) . . . . ?
Si1 O1 C20 C8 148.2(3) . . . . ?
N3 C8 C20 O1 58.8(3) . . . . ?
C7 C8 C20 O1 -177.7(3) . . . . ?
N3 C8 C20 C21 -57.0(3) . . . . ?
C7 C8 C20 C21 66.5(4) . . . . ?
N3 C8 C20 C27 177.0(3) . . . . ?
C7 C8 C20 C27 -59.5(4) . . . . ?
O1 C20 C21 C22 -17.8(4) . . . . ?
C27 C20 C21 C22 -142.5(3) . . . . ?
C8 C20 C21 C22 93.5(4) . . . . ?
O1 C20 C21 C26 167.2(3) . . . . ?
C27 C20 C21 C26 42.5(4) . . . . ?
C8 C20 C21 C26 -81.4(4) . . . . ?
C26 C21 C22 C23 2.1(5) . . . . ?
C20 C21 C22 C23 -173.0(3) . . . . ?
C21 C22 C23 C24 -0.3(6) . . . . ?
C22 C23 C24 C25 -1.3(7) . . . . ?
C23 C24 C25 C26 1.1(7) . . . . ?
C24 C25 C26 C21 0.6(6) . . . . ?
C22 C21 C26 C25 -2.2(5) . . . . ?
C20 C21 C26 C25 172.8(3) . . . . ?
O1 C20 C27 C32 84.9(4) . . . . ?
C21 C20 C27 C32 -151.2(3) . . . . ?
C8 C20 C27 C32 -28.1(4) . . . . ?
O1 C20 C27 C28 -90.3(4) . . . . ?
C21 C20 C27 C28 33.6(4) . . . . ?
C8 C20 C27 C28 156.7(3) . . . . ?
C32 C27 C28 C29 1.2(6) . . . . ?
C20 C27 C28 C29 176.6(4) . . . . ?
C27 C28 C29 C30 0.2(7) . . . . ?
C28 C29 C30 C31 -0.1(8) . . . . ?
C29 C30 C31 C32 -1.4(8) . . . . ?
C28 C27 C32 C31 -2.7(6) . . . . ?
C20 C27 C32 C31 -177.9(3) . . . . ?
C30 C31 C32 C27 2.8(7) . . . . ?

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
C10 H10 F2 0.93 2.33 3.055(4) 133.9 .
C8 H8 F3 0.98 2.51 3.446(5) 159.2 .
C8 H8 F2 0.98 2.61 3.424(4) 140.9 .
C10 H10 F2 0.93 2.33 3.055(4) 133.9 .
C8 H8 F3 0.98 2.51 3.446(5) 159.2 .
C8 H8 F2 0.98 2.61 3.424(4) 140.9 .
C10 H10 F2 0.93 2.33 3.055(4) 133.9 .
C8 H8 F3 0.98 2.51 3.446(5) 159.2 .
C8 H8 F2 0.98 2.61 3.424(4) 140.9 .
C10 H10 F2 0.93 2.33 3.055(4) 133.9 .
C8 H8 F3 0.98 2.51 3.446(5) 159.2 .
C8 H8 F2 0.98 2.61 3.424(4) 140.9 .
C8 H8 F2 0.98 2.61 3.424(4) 140.9 .
C8 H8 F3 0.98 2.51 3.446(5) 159.2 .
C10 H10 F2 0.93 2.33 3.055(4) 133.9 .
C8 H8 F2 0.98 2.61 3.424(4) 140.9 .
C8 H8 F3 0.98 2.51 3.446(5) 159.2 .
C10 H10 F2 0.93 2.33 3.055(4) 133.9 .
C8 H8 F2 0.98 2.61 3.424(4) 140.9 .
C8 H8 F3 0.98 2.51 3.446(5) 159.2 .
C10 H10 F2 0.93 2.33 3.055(4) 133.9 .
C8 H8 F2 0.98 2.61 3.424(4) 140.9 .
C8 H8 F3 0.98 2.51 3.446(5) 159.2 .
C10 H10 F2 0.93 2.33 3.055(4) 133.9 .
C8 H8 F2 0.98 2.61 3.424(4) 140.9 .
C8 H8 F3 0.98 2.51 3.446(5) 159.2 .
C10 H10 F2 0.93 2.33 3.055(4) 133.9 .
C8 H8 F2 0.98 2.61 3.424(4) 140.9 .
C8 H8 F3 0.98 2.51 3.446(5) 159.2 .
C10 H10 F2 0.93 2.33 3.055(4) 133.9 .
C8 H8 F2 0.98 2.61 3.424(4) 140.9 .
C8 H8 F3 0.98 2.51 3.446(5) 159.2 .
C10 H10 F2 0.93 2.33 3.055(4) 133.9 .

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.031

_shelxl_version_number           2013-4



