# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_JF3111F3_60MI
_database_code_depnum_ccdc_archive 'CCDC 2289933'
loop_
_audit_author_name
_audit_author_address
'James C. Fettinger'
;University of California, Davis
United States of America
;
_audit_update_record             
;
2023-08-21 deposited with the CCDC.	2025-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H35 F N2 O2 Si'
_chemical_formula_sum            'C24 H35 F N2 O2 Si'
_chemical_formula_weight         430.63

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'
F F 0.0171 0.0103 '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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           178
_space_group_name_H-M_alt        'P 61 2 2'
_space_group_name_Hall           'P 61 2 (0 0 -1)'

_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'
'-x, -y, z+1/2'
'y, -x+y, z+5/6'
'x-y, x, z+1/6'
'y, x, -z+1/3'
'x-y, -y, -z'
'-x, -x+y, -z+2/3'
'-y, -x, -z+5/6'
'-x+y, y, -z+1/2'
'x, x-y, -z+1/6'

_cell_length_a                   11.3851(8)
_cell_length_b                   11.3851(8)
_cell_length_c                   64.721(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     7265.2(13)
_cell_formula_units_Z            12
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9664
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      30.48

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_F_000             2784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.331
_exptl_crystal_size_min          0.134
_exptl_absorpt_coefficient_mu    0.126
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8361
_exptl_absorpt_correction_T_max  0.9185
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Photon2 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            63449
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -92
_diffrn_reflns_limit_l_max       90
_diffrn_reflns_theta_min         1.888
_diffrn_reflns_theta_max         30.550
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7401
_reflns_number_gt                7034
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.644
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       'Apex3 (2019.11-0) (Bruker, 2019)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;

26 July, 2022 JF3111 Kappa Venture 100K

A colorless block with approximate orthogonal dimensions 0.134 x 0.331
x 0.380mm3 was placed and optically centered on the Bruker(1) Venture
Dual source Kappa diffractometer with Photon2 CMOS detector at
â\/E?173Â°C(100K).  Indexing of the unit cell used a random set of
reflections collected from three series of 0.5Â° wide omega-scans, 5
seconds per frame, and 30 frames per series that were well distributed
in reciprocal space. Data were collected [MoKa] with 0.3Â° wide scans,
variable time per frame dependent upon detector 2theta angle and
varying phi and omega angles such that nearly all unique reflections
were collected at least once.  The crystal to detector distance was
65.00mm, thus providing a complete sphere of data to 2thetamax=61.10Â°.

Structural determination and Refinement:

All crystallographic calculations were performed on a Surface Pro7
with Intel i7-1065G7 at 1.30GHz with four cores, eight processors and
16GB of extended memory. Data collected were corrected for Lorentz and
polarization effects with Saint(1) and absorption using Blessingâ\/E?s
method and merged as incorporated with the program Sadabs(2,3). The
SHELXTL(4) program package was implemented to determine the probable
space group and set up the initial files. System symmetry, systematic
absences and intensity statistics indicated the standard non-
centrosymmetric hexagonal space group P6122 (no. 178). The structure
was determined by direct methods with nearly all non-hydrogen atoms
being located directly for the molecule using the program XT(5). The
structure was refined with XL(6). The 113873 data collected were
merged, based upon identical indices, to 63537 data, and then merged
for least squares refinement to 7401 unique data [R(int)=0.0386]. All
non- hydrogen atoms were refined anisotropically. All hydrogen atoms
were initially idealized and then allowed to refine freely during the
final refinement stage. The final structure was refined to convergence
with R(F)=4.04%, wR(F2)=9.33%, GOF=1.152 for all 7401 unique
reflections [R(F)=3.78, wR(F2)=9.20% for those 7034 data with Fo >
4sigma(Fo)]. The final difference-Fourier map was featureless
indicating that the structure is both correct and complete.  An
empirical correction for extinction was also attempted but found to be
negative and therefore not applied.

References:

1.	Bruker (2019) APEX3 (Version 2019.0) and (2016) SAINT (Version
8.37a). Bruker AXS Inc., Madison, Wisconsin, USA. 2.	An Empirical
Correction for Absorption Anisotropy, Blessing, R. H. (1995). Acta
Cryst., A51, 33-38.

3.	Sheldrick, G.M., SADABS (2016) Version 2016/2, â\/E?Siemens Area
Detector Absorption Correctionâ\/E? UniversitÃ?t GÃ?ttingen: GÃ?ttingen,
Germany.

4.	Sheldrick, G.M., (2002). SHELXTL. Version 6.1. Bruker AXS Inc.,
Madison, Wisconsin, USA.

5.	Sheldrick, G. M., (2014) SHELXT, UniversitÃ?t GÃ?ttingen: GÃ?ttingen,
Germany.  Structure determination program. Private communication.

6.	Sheldrick, G. M., (2017). SHELXL2017/1. UniversitÃ?t GÃ?ttingen:
GÃ?ttingen, Germany.


;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0324P)²+2.8159P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2653 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.01(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7401
_refine_ls_number_parameters     411
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0933
_refine_ls_wR_factor_gt          0.0920
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_restrained_S_all      1.152
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 1.09460(5) 0.37080(5) 0.04052(2) 0.01733(10) Uani 1 1 d . . . . .
C1 C 1.0026(2) 0.23335(19) 0.02078(3) 0.0226(3) Uani 1 1 d . . . . .
H1 H 1.064(3) 0.254(3) 0.0096(4) 0.032(7) Uiso 1 1 d . . . . .
O1 O 0.98221(12) 0.34595(13) 0.05851(2) 0.0184(2) Uani 1 1 d . . . . .
H1A H 1.008(3) 0.376(3) 0.0705(4) 0.036(7) Uiso 1 1 d . . . . .
C2 C 0.8776(2) 0.2360(2) 0.01251(3) 0.0249(4) Uani 1 1 d . . . . .
H2A H 0.829(3) 0.166(3) 0.0022(4) 0.028(6) Uiso 1 1 d . . . . .
H2B H 0.903(3) 0.323(3) 0.0063(4) 0.024(6) Uiso 1 1 d . . . . .
H2C H 0.811(3) 0.215(3) 0.0242(4) 0.037(7) Uiso 1 1 d . . . . .
C3 C 0.9626(3) 0.0913(2) 0.02883(4) 0.0350(5) Uani 1 1 d . . . . .
H3A H 0.911(3) 0.075(3) 0.0418(5) 0.047(8) Uiso 1 1 d . . . . .
H3B H 1.045(4) 0.082(3) 0.0322(5) 0.054(9) Uiso 1 1 d . . . . .
H3C H 0.911(4) 0.020(4) 0.0182(6) 0.068(11) Uiso 1 1 d . . . . .
C4 C 1.24839(19) 0.3758(2) 0.05199(3) 0.0264(4) Uani 1 1 d . . . . .
H4 H 1.293(3) 0.359(2) 0.0399(4) 0.024(6) Uiso 1 1 d . . . . .
C5 C 1.3437(2) 0.5157(3) 0.06129(4) 0.0391(5) Uani 1 1 d . . . . .
H5A H 1.298(3) 0.539(3) 0.0718(5) 0.052(9) Uiso 1 1 d . . . . .
H5B H 1.386(3) 0.591(3) 0.0503(5) 0.047(8) Uiso 1 1 d . . . . .
H5C H 1.417(3) 0.514(3) 0.0685(4) 0.043(8) Uiso 1 1 d . . . . .
C6 C 1.2105(3) 0.2646(3) 0.06842(4) 0.0340(5) Uani 1 1 d . . . . .
H6A H 1.285(3) 0.266(3) 0.0736(4) 0.037(7) Uiso 1 1 d . . . . .
H6B H 1.153(3) 0.175(3) 0.0628(5) 0.047(8) Uiso 1 1 d . . . . .
H6C H 1.162(3) 0.281(3) 0.0798(4) 0.030(6) Uiso 1 1 d . . . . .
C7 C 1.14680(17) 0.53638(18) 0.02647(3) 0.0189(3) Uani 1 1 d . . . . .
C8 C 1.23566(19) 0.5744(2) 0.00981(3) 0.0223(3) Uani 1 1 d . . . . .
F8 F 1.29033(13) 0.49366(13) 0.00517(2) 0.0290(3) Uani 1 1 d . . . . .
C9 C 1.2755(2) 0.6867(2) -0.00253(3) 0.0256(4) Uani 1 1 d . . . . .
H9 H 1.340(2) 0.703(2) -0.0132(3) 0.020(6) Uiso 1 1 d . . . . .
C10 C 1.2179(2) 0.7669(2) 0.00112(3) 0.0260(4) Uani 1 1 d . . . . .
H10 H 1.241(3) 0.845(3) -0.0072(4) 0.032(7) Uiso 1 1 d . . . . .
C11 C 1.12612(19) 0.73417(19) 0.01727(3) 0.0227(3) Uani 1 1 d . . . . .
H11 H 1.087(3) 0.787(3) 0.0203(4) 0.024(6) Uiso 1 1 d . . . . .
C12 C 1.09441(17) 0.62328(17) 0.03004(3) 0.0177(3) Uani 1 1 d . . . . .
C13 C 1.00696(17) 0.60573(17) 0.04859(3) 0.0168(3) Uani 1 1 d . . . . .
N13 N 0.87763(15) 0.56851(15) 0.04393(2) 0.0175(3) Uani 1 1 d . . . . .
H13 H 0.853(2) 0.551(2) 0.0313(4) 0.023(6) Uiso 1 1 d . . . . .
O13 O 1.05472(13) 0.63010(14) 0.06621(2) 0.0214(3) Uani 1 1 d . . . . .
C14 C 0.77565(17) 0.54974(17) 0.05933(3) 0.0168(3) Uani 1 1 d . . . . .
H14 H 0.815(2) 0.552(2) 0.0729(3) 0.010(5) Uiso 1 1 d . . . . .
C15 C 0.64998(17) 0.40989(19) 0.05657(3) 0.0195(3) Uani 1 1 d . . . . .
H15A H 0.585(2) 0.398(2) 0.0675(3) 0.017(5) Uiso 1 1 d . . . . .
H15B H 0.605(2) 0.404(2) 0.0435(4) 0.021(6) Uiso 1 1 d . . . . .
N15 N 0.68724(16) 0.30617(17) 0.05697(3) 0.0253(3) Uani 1 1 d . . . . .
H15 H 0.767(2) 0.328(2) 0.0581(3) 0.015(5) Uiso 1 1 d . . . . .
C16 C 0.59340(18) 0.17032(18) 0.05489(3) 0.0198(3) Uani 1 1 d . . . . .
C17 C 0.45481(19) 0.1240(2) 0.05191(3) 0.0231(4) Uani 1 1 d . . . . .
H17 H 0.424(3) 0.185(3) 0.0517(4) 0.023(6) Uiso 1 1 d . . . . .
C18 C 0.3645(2) -0.0140(2) 0.04953(3) 0.0293(4) Uani 1 1 d . . . . .
H18 H 0.268(3) -0.047(3) 0.0480(4) 0.037(7) Uiso 1 1 d . . . . .
C19 C 0.4072(2) -0.1082(2) 0.05047(4) 0.0333(5) Uani 1 1 d . . . . .
H19 H 0.348(3) -0.203(3) 0.0492(5) 0.050(9) Uiso 1 1 d . . . . .
C20 C 0.5436(2) -0.0626(2) 0.05379(3) 0.0278(4) Uani 1 1 d . . . . .
H20 H 0.576(3) -0.129(3) 0.0553(4) 0.038(7) Uiso 1 1 d . . . . .
C21 C 0.63582(19) 0.07417(18) 0.05598(3) 0.0212(3) Uani 1 1 d . . . . .
H21 H 0.726(3) 0.101(2) 0.0594(4) 0.024(6) Uiso 1 1 d . . . . .
C22 C 0.7426(2) 0.66539(19) 0.05838(3) 0.0214(3) Uani 1 1 d . . . . .
H22 H 0.668(2) 0.640(2) 0.0681(4) 0.021(6) Uiso 1 1 d . . . . .
C23 C 0.8649(2) 0.7979(2) 0.06551(3) 0.0297(4) Uani 1 1 d . . . . .
H23A H 0.937(3) 0.820(3) 0.0561(4) 0.037(7) Uiso 1 1 d . . . . .
H23B H 0.898(3) 0.793(3) 0.0792(4) 0.028(6) Uiso 1 1 d . . . . .
H23C H 0.839(3) 0.873(3) 0.0662(4) 0.040(8) Uiso 1 1 d . . . . .
C24 C 0.6957(3) 0.6823(3) 0.03702(3) 0.0315(4) Uani 1 1 d . . . . .
H24A H 0.670(3) 0.755(3) 0.0379(5) 0.051(9) Uiso 1 1 d . . . . .
H24B H 0.617(3) 0.597(3) 0.0320(5) 0.047(8) Uiso 1 1 d . . . . .
H24C H 0.760(3) 0.701(3) 0.0266(4) 0.039(7) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si1 O1 1.6465(13) . ?
Si1 C4 1.8762(19) . ?
Si1 C1 1.8813(19) . ?
Si1 C7 1.9012(19) . ?
C1 C2 1.535(3) . ?
C1 C3 1.535(3) . ?
C1 H1 0.95(3) . ?
O1 H1A 0.84(3) . ?
C2 H2A 0.97(3) . ?
C2 H2B 0.97(2) . ?
C2 H2C 1.01(3) . ?
C3 H3A 0.99(3) . ?
C3 H3B 1.02(4) . ?
C3 H3C 1.00(4) . ?
C4 C5 1.533(3) . ?
C4 C6 1.541(3) . ?
C4 H4 1.00(2) . ?
C5 H5A 0.97(3) . ?
C5 H5B 1.03(3) . ?
C5 H5C 0.96(3) . ?
C6 H6A 0.90(3) . ?
C6 H6B 0.97(3) . ?
C6 H6C 1.00(3) . ?
C7 C8 1.391(2) . ?
C7 C12 1.407(3) . ?
C8 F8 1.377(2) . ?
C8 C9 1.378(3) . ?
C9 C10 1.385(3) . ?
C9 H9 0.95(2) . ?
C10 C11 1.391(3) . ?
C10 H10 0.96(3) . ?
C11 C12 1.397(3) . ?
C11 H11 0.93(3) . ?
C12 C13 1.508(2) . ?
C13 O13 1.233(2) . ?
C13 N13 1.347(2) . ?
N13 C14 1.462(2) . ?
N13 H13 0.85(2) . ?
C14 C15 1.528(2) . ?
C14 C22 1.541(2) . ?
C14 H14 0.98(2) . ?
C15 N15 1.441(2) . ?
C15 H15A 0.98(2) . ?
C15 H15B 0.97(2) . ?
N15 C16 1.378(2) . ?
N15 H15 0.81(2) . ?
C16 C21 1.402(3) . ?
C16 C17 1.405(3) . ?
C17 C18 1.391(3) . ?
C17 H17 0.92(2) . ?
C18 C19 1.382(3) . ?
C18 H18 0.97(3) . ?
C19 C20 1.386(3) . ?
C19 H19 0.95(3) . ?
C20 C21 1.383(3) . ?
C20 H20 0.99(3) . ?
C21 H21 0.94(3) . ?
C22 C23 1.526(3) . ?
C22 C24 1.529(3) . ?
C22 H22 0.98(2) . ?
C23 H23A 0.95(3) . ?
C23 H23B 0.98(2) . ?
C23 H23C 1.03(3) . ?
C24 H24A 1.01(3) . ?
C24 H24B 0.99(3) . ?
C24 H24C 0.94(3) . ?

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 C4 111.03(8) . . ?
O1 Si1 C1 106.00(8) . . ?
C4 Si1 C1 114.63(9) . . ?
O1 Si1 C7 109.85(7) . . ?
C4 Si1 C7 109.57(9) . . ?
C1 Si1 C7 105.53(8) . . ?
C2 C1 C3 110.46(18) . . ?
C2 C1 Si1 110.89(13) . . ?
C3 C1 Si1 113.21(14) . . ?
C2 C1 H1 107.7(16) . . ?
C3 C1 H1 108.0(17) . . ?
Si1 C1 H1 106.3(16) . . ?
Si1 O1 H1A 120(2) . . ?
C1 C2 H2A 112.3(15) . . ?
C1 C2 H2B 111.2(15) . . ?
H2A C2 H2B 108(2) . . ?
C1 C2 H2C 108.7(16) . . ?
H2A C2 H2C 105(2) . . ?
H2B C2 H2C 111(2) . . ?
C1 C3 H3A 109.0(18) . . ?
C1 C3 H3B 112.2(19) . . ?
H3A C3 H3B 107(3) . . ?
C1 C3 H3C 112(2) . . ?
H3A C3 H3C 112(3) . . ?
H3B C3 H3C 105(3) . . ?
C5 C4 C6 110.17(19) . . ?
C5 C4 Si1 110.60(15) . . ?
C6 C4 Si1 112.02(15) . . ?
C5 C4 H4 109.9(15) . . ?
C6 C4 H4 110.2(14) . . ?
Si1 C4 H4 103.7(14) . . ?
C4 C5 H5A 111(2) . . ?
C4 C5 H5B 112.6(18) . . ?
H5A C5 H5B 111(3) . . ?
C4 C5 H5C 109.6(18) . . ?
H5A C5 H5C 105(3) . . ?
H5B C5 H5C 108(2) . . ?
C4 C6 H6A 111.6(19) . . ?
C4 C6 H6B 111.8(18) . . ?
H6A C6 H6B 107(3) . . ?
C4 C6 H6C 107.9(15) . . ?
H6A C6 H6C 109(2) . . ?
H6B C6 H6C 110(2) . . ?
C8 C7 C12 113.99(16) . . ?
C8 C7 Si1 119.85(14) . . ?
C12 C7 Si1 125.91(13) . . ?
F8 C8 C9 116.42(16) . . ?
F8 C8 C7 117.52(17) . . ?
C9 C8 C7 126.07(18) . . ?
C8 C9 C10 117.92(17) . . ?
C8 C9 H9 117.6(15) . . ?
C10 C9 H9 124.4(14) . . ?
C9 C10 C11 119.45(18) . . ?
C9 C10 H10 120.7(16) . . ?
C11 C10 H10 119.8(16) . . ?
C10 C11 C12 120.46(18) . . ?
C10 C11 H11 121.5(15) . . ?
C12 C11 H11 118.0(15) . . ?
C11 C12 C7 121.97(16) . . ?
C11 C12 C13 116.49(16) . . ?
C7 C12 C13 121.46(15) . . ?
O13 C13 N13 124.56(16) . . ?
O13 C13 C12 121.23(15) . . ?
N13 C13 C12 114.14(15) . . ?
C13 N13 C14 123.83(14) . . ?
C13 N13 H13 117.5(17) . . ?
C14 N13 H13 118.6(17) . . ?
N13 C14 C15 109.53(14) . . ?
N13 C14 C22 111.33(14) . . ?
C15 C14 C22 112.59(15) . . ?
N13 C14 H14 106.9(12) . . ?
C15 C14 H14 108.0(12) . . ?
C22 C14 H14 108.3(12) . . ?
N15 C15 C14 110.24(14) . . ?
N15 C15 H15A 112.5(14) . . ?
C14 C15 H15A 108.0(14) . . ?
N15 C15 H15B 108.5(14) . . ?
C14 C15 H15B 111.3(14) . . ?
H15A C15 H15B 106.3(19) . . ?
C16 N15 C15 122.50(16) . . ?
C16 N15 H15 118.4(16) . . ?
C15 N15 H15 119.0(16) . . ?
N15 C16 C21 119.67(17) . . ?
N15 C16 C17 121.98(18) . . ?
C21 C16 C17 118.35(17) . . ?
C18 C17 C16 119.76(19) . . ?
C18 C17 H17 120.2(16) . . ?
C16 C17 H17 120.1(16) . . ?
C19 C18 C17 121.57(19) . . ?
C19 C18 H18 118.3(17) . . ?
C17 C18 H18 120.0(17) . . ?
C18 C19 C20 118.62(19) . . ?
C18 C19 H19 123.5(19) . . ?
C20 C19 H19 117.9(19) . . ?
C21 C20 C19 121.0(2) . . ?
C21 C20 H20 118.8(16) . . ?
C19 C20 H20 120.1(17) . . ?
C20 C21 C16 120.64(18) . . ?
C20 C21 H21 118.8(15) . . ?
C16 C21 H21 120.3(15) . . ?
C23 C22 C24 110.61(17) . . ?
C23 C22 C14 109.92(16) . . ?
C24 C22 C14 113.17(15) . . ?
C23 C22 H22 109.3(14) . . ?
C24 C22 H22 108.0(14) . . ?
C14 C22 H22 105.6(14) . . ?
C22 C23 H23A 107.9(17) . . ?
C22 C23 H23B 114.0(15) . . ?
H23A C23 H23B 107(2) . . ?
C22 C23 H23C 109.7(17) . . ?
H23A C23 H23C 112(2) . . ?
H23B C23 H23C 106(2) . . ?
C22 C24 H24A 108.5(17) . . ?
C22 C24 H24B 111.7(18) . . ?
H24A C24 H24B 110(3) . . ?
C22 C24 H24C 113.6(17) . . ?
H24A C24 H24C 111(2) . . ?
H24B C24 H24C 102(2) . . ?

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 Si1 C1 C2 56.41(15) . . . . ?
C4 Si1 C1 C2 179.25(13) . . . . ?
C7 Si1 C1 C2 -60.09(15) . . . . ?
O1 Si1 C1 C3 -68.39(17) . . . . ?
C4 Si1 C1 C3 54.44(18) . . . . ?
C7 Si1 C1 C3 175.11(16) . . . . ?
O1 Si1 C4 C5 -80.80(17) . . . . ?
C1 Si1 C4 C5 159.12(15) . . . . ?
C7 Si1 C4 C5 40.71(17) . . . . ?
O1 Si1 C4 C6 42.52(18) . . . . ?
C1 Si1 C4 C6 -77.56(17) . . . . ?
C7 Si1 C4 C6 164.04(15) . . . . ?
C12 C7 C8 F8 -179.38(15) . . . . ?
Si1 C7 C8 F8 -4.8(2) . . . . ?
C12 C7 C8 C9 1.2(3) . . . . ?
Si1 C7 C8 C9 175.79(16) . . . . ?
F8 C8 C9 C10 177.20(18) . . . . ?
C7 C8 C9 C10 -3.3(3) . . . . ?
C8 C9 C10 C11 1.9(3) . . . . ?
C9 C10 C11 C12 1.5(3) . . . . ?
C10 C11 C12 C7 -3.8(3) . . . . ?
C10 C11 C12 C13 173.02(17) . . . . ?
C8 C7 C12 C11 2.4(2) . . . . ?
Si1 C7 C12 C11 -171.83(14) . . . . ?
C8 C7 C12 C13 -174.20(16) . . . . ?
Si1 C7 C12 C13 11.6(2) . . . . ?
C11 C12 C13 O13 -107.2(2) . . . . ?
C7 C12 C13 O13 69.6(2) . . . . ?
C11 C12 C13 N13 69.8(2) . . . . ?
C7 C12 C13 N13 -113.45(18) . . . . ?
O13 C13 N13 C14 -1.1(3) . . . . ?
C12 C13 N13 C14 -177.98(15) . . . . ?
C13 N13 C14 C15 -127.30(17) . . . . ?
C13 N13 C14 C22 107.54(19) . . . . ?
N13 C14 C15 N15 53.9(2) . . . . ?
C22 C14 C15 N15 178.29(15) . . . . ?
C14 C15 N15 C16 179.77(17) . . . . ?
C15 N15 C16 C21 -178.25(17) . . . . ?
C15 N15 C16 C17 1.0(3) . . . . ?
N15 C16 C17 C18 178.82(19) . . . . ?
C21 C16 C17 C18 -1.9(3) . . . . ?
C16 C17 C18 C19 1.5(3) . . . . ?
C17 C18 C19 C20 -0.3(3) . . . . ?
C18 C19 C20 C21 -0.5(3) . . . . ?
C19 C20 C21 C16 0.0(3) . . . . ?
N15 C16 C21 C20 -179.54(18) . . . . ?
C17 C16 C21 C20 1.1(3) . . . . ?
N13 C14 C22 C23 -67.98(19) . . . . ?
C15 C14 C22 C23 168.58(16) . . . . ?
N13 C14 C22 C24 56.2(2) . . . . ?
C15 C14 C22 C24 -67.2(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1A O13 0.84(3) 2.01(3) 2.8489(18) 173(3) 12 yes
N13 H13 F8 0.85(2) 2.43(2) 3.2864(19) 177(2) 8_565 yes
N15 H15 O1 0.81(2) 2.36(2) 3.158(2) 168(2) . yes

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_JF3275KFMI
_database_code_depnum_ccdc_archive 'CCDC 2289938'
loop_
_audit_author_name
_audit_author_address
'James C. Fettinger'
;University of California, Davis
United States of America
;
_audit_update_record             
;
2023-08-21 deposited with the CCDC.	2025-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H21 F N2 O'
_chemical_formula_sum            'C18 H21 F N2 O'
_chemical_formula_weight         300.37

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'
F F 0.0727 0.0534 '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                   5.2703(3)
_cell_length_b                   13.9801(9)
_cell_length_c                   21.4626(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1581.35(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    9910
_cell_measurement_theta_min      3.77
_cell_measurement_theta_max      74.47

_exptl_crystal_description       Rod
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.519
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.703
_shelx_estimated_absorpt_T_min   0.712
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5381
_exptl_absorpt_correction_T_max  0.8176
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Photon2 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7941
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.773
_diffrn_reflns_theta_max         74.626
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3222
_reflns_number_gt                3093
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_max     0.984
_reflns_Friedel_fraction_full    0.997

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

_computing_data_collection       'Apex3 (2019.11-0) (Bruker, 2019)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    
'SHELXT (Sheldrick, 2015) Acta Cryst., A71, 3-8'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;

17 August, 2023 JF3275 Kappa Duo Cu  (YPC-4-138-SM)

A colorless rod with approximate orthogonal dimensions 0.050 x 0.177 x
0.519mm3 was placed and optically centered on the Bruker(1) Venture
Dual source Kappa Photon2 diffractometer at â\/E?83Â°C(190K).  Indexing of
the unit cell used a random set of reflections collected from three
series of 0.5Â° wide omega-scans, 10 seconds per frame, and 30 frames
per series that were well distributed in reciprocal space using CuKa
radiation. Data were collected [CuKa] with 0.5Â° wide scans, variable
time per frame dependent upon detector 2theta angle and varying phi
and omega angles such that nearly all unique reflections were
collected at least once. The crystal to detector distance was 6.50cm,
thus providing a complete sphere of data to 2thetamax= 148.99Â°.

Structural determination and Refinement:

All crystallographic calculations were performed on a Surface Pro7
with Intel i7-1065G7 at 1.30GHz with four cores, eight processors and
16GB of extended memory. Data collected were corrected for Lorentz and
polarization effects with Saint(1) and absorption using Blessingâ\/E?s
method and merged as incorporated with the program Sadabs(2,3). The
SHELXTL(4) program package was implemented to determine the probable
space group and set up the initial files. System symmetry, systematic
absences and intensity statistics indicated the non-centrosymmetric
orthorhombic space group P212121 (no. 19). The structure was
determined by direct methods with the non-hydrogen atoms for the
molecule being located using the program XT(5).  The structure was
refined with XL(6). The 12076 data collected were merged based upon
identical indices to 7941, then merged for least squares refinement to
3222 unique data [R(int)=0.0582]. All non-hydrogen atoms were refined
anisotropically. Hydrogen atoms were idealized initially and then
allowed to refine freely throughout the final refinement stages. The
final structure was refined to convergence with R(F)=4.55%,
wR(F2)=12.00%, GOF=1.050 for all 3222 unique reflections [R(F)=4.43%,
wR(F2)=11.79% for those 3093 data with Fo > 4sigma(Fo)]. The final
difference-Fourier map was featureless indicating that the structure
is both correct and complete. An empirical correction for extinction
was also attempted and found to be negative and therefore not applied.
The absolute structure parameters were determined to be: Flack(x)7, -
0.03(13); Hooft(y)8, -0.02(11) and the Parsons(z)6, -0.04(10)
indicating that the structureâ\/E?s absolute configuration has been
determined reliably; these values would be close to 1.0 if the
structure were inverted.

References:

1.	Bruker (2019) APEXII (Version 2019.0) and (2016) SAINT (Version
8.37a). Bruker AXS Inc., Madison, Wisconsin, USA.

2.	An Empirical Correction for Absorption Anisotropy, Blessing, R. H.
(1995). Acta Cryst., A51, 33-38.

3.	Sheldrick, G.M., SADABS (2016) Version 2016/2, â\/E?Siemens Area
Detector Absorption Correctionâ\/E? UniversitÃ?t GÃ?ttingen: GÃ?ttingen,
Germany.

4.	Sheldrick, G.M., (2002). SHELXTL. Version 6.1. Bruker AXS Inc.,
Madison, Wisconsin, USA.

5.	Sheldrick, G. M., (2014) SHELXT, UniversitÃ?t GÃ?ttingen: GÃ?ttingen,
Germany.  Structure determination program. Private communication.

6.	Sheldrick, G. M., (2018). SHELXL2018/3. UniversitÃ?t GÃ?ttingen:
GÃ?ttingen, Germany.

7.	On Enantiomorph-Polarity Estimation, Flack, H.D. (1983). Acta
Cryst., A39, 876-881.

8.	Hooft, R.W.W, Straver, L.H. & Spek, A.L. (2008). J. Appl, Cryst.
41, 96-103. Thompson,A.L. & Watkin, D.J. (2009). Tetrahedron


Acknowledgment:  We thank the National Science Foundation (Grant CHE-
1531193) for the Dual Source X-ray diffractometer.

James C. Fettinger, UC Davis

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0748P)²+0.1092P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1241 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.03(13)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3222
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1200
_refine_ls_wR_factor_gt          0.1179
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4841(4) 0.39517(15) 0.78365(9) 0.0400(4) Uani 1 1 d . . . . .
H1 H 0.350(5) 0.4293(15) 0.8019(10) 0.028(5) Uiso 1 1 d . . . . .
N1 N 0.5174(3) 0.43553(13) 0.72108(8) 0.0406(4) Uani 1 1 d . . . . .
H1A H 0.664(5) 0.4423(16) 0.7068(12) 0.035(6) Uiso 1 1 d . . . . .
C2 C 0.3209(4) 0.46668(14) 0.68747(9) 0.0394(4) Uani 1 1 d . . . . .
O2 O 0.1005(3) 0.46553(13) 0.70669(7) 0.0488(4) Uani 1 1 d . . . . .
C3 C 0.3807(4) 0.50484(14) 0.62352(9) 0.0403(4) Uani 1 1 d . . . . .
C4 C 0.2151(5) 0.57128(16) 0.59813(11) 0.0475(5) Uani 1 1 d . . . . .
H4 H 0.072(7) 0.589(2) 0.6208(14) 0.062(8) Uiso 1 1 d . . . . .
C5 C 0.2674(5) 0.60768(19) 0.53982(12) 0.0571(6) Uani 1 1 d . . . . .
F5 F 0.1066(4) 0.67404(14) 0.51570(9) 0.0869(6) Uani 1 1 d . . . . .
C6 C 0.4733(5) 0.5800(2) 0.50560(11) 0.0621(7) Uani 1 1 d . . . . .
H6 H 0.491(7) 0.608(2) 0.4668(16) 0.072(9) Uiso 1 1 d . . . . .
C7 C 0.6338(5) 0.5130(2) 0.53060(12) 0.0615(6) Uani 1 1 d . . . . .
H7 H 0.773(8) 0.492(3) 0.5076(17) 0.078(9) Uiso 1 1 d . . . . .
C8 C 0.5911(4) 0.47516(18) 0.58963(10) 0.0485(5) Uani 1 1 d . . . . .
H8 H 0.714(6) 0.429(2) 0.6057(15) 0.063(8) Uiso 1 1 d . . . . .
C9 C 0.7280(4) 0.41156(17) 0.82119(10) 0.0454(5) Uani 1 1 d . . . . .
H9A H 0.705(5) 0.3831(18) 0.8644(12) 0.047(7) Uiso 1 1 d . . . . .
H9B H 0.872(5) 0.3759(19) 0.8019(12) 0.044(6) Uiso 1 1 d . . . . .
N9 N 0.8121(4) 0.50922(16) 0.82569(10) 0.0532(5) Uani 1 1 d . . . . .
H9 H 0.942(6) 0.526(2) 0.8014(13) 0.050(7) Uiso 1 1 d . . . . .
C10 C 0.7031(4) 0.57751(17) 0.86363(9) 0.0430(4) Uani 1 1 d . . . . .
C11 C 0.8152(4) 0.66829(18) 0.86639(11) 0.0492(5) Uani 1 1 d . . . . .
H11 H 0.967(6) 0.6791(18) 0.8437(13) 0.049(7) Uiso 1 1 d . . . . .
C12 C 0.7141(5) 0.73896(18) 0.90400(12) 0.0576(6) Uani 1 1 d . . . . .
H12 H 0.808(7) 0.802(2) 0.9039(15) 0.064(8) Uiso 1 1 d . . . . .
C13 C 0.5009(6) 0.72159(19) 0.94003(12) 0.0583(6) Uani 1 1 d . . . . .
H13 H 0.424(6) 0.773(2) 0.9670(14) 0.059(8) Uiso 1 1 d . . . . .
C14 C 0.3910(5) 0.63197(19) 0.93818(11) 0.0518(5) Uani 1 1 d . . . . .
H14 H 0.246(6) 0.622(2) 0.9622(13) 0.051(7) Uiso 1 1 d . . . . .
C15 C 0.4895(4) 0.56010(17) 0.90039(10) 0.0460(5) Uani 1 1 d . . . . .
H15 H 0.397(5) 0.4991(19) 0.8998(12) 0.045(6) Uiso 1 1 d . . . . .
C16 C 0.4086(4) 0.28877(16) 0.78038(10) 0.0451(5) Uani 1 1 d . . . . .
H16 H 0.257(5) 0.2833(17) 0.7548(11) 0.034(5) Uiso 1 1 d . . . . .
C17 C 0.3233(6) 0.2514(2) 0.84404(13) 0.0597(6) Uani 1 1 d . . . . .
H17A H 0.249(7) 0.187(2) 0.8386(15) 0.070(9) Uiso 1 1 d . . . . .
H17B H 0.185(7) 0.292(2) 0.8629(15) 0.063(8) Uiso 1 1 d . . . . .
H17C H 0.475(7) 0.245(2) 0.8732(16) 0.069(9) Uiso 1 1 d . . . . .
C18 C 0.6164(5) 0.22531(18) 0.75267(13) 0.0540(5) Uani 1 1 d . . . . .
H18A H 0.766(6) 0.2212(19) 0.7781(13) 0.048(6) Uiso 1 1 d . . . . .
H18B H 0.668(7) 0.253(2) 0.7132(15) 0.064(8) Uiso 1 1 d . . . . .
H18C H 0.546(6) 0.161(2) 0.7476(16) 0.067(8) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.467(2) . ?
C1 C9 1.534(3) . ?
C1 C16 1.541(3) . ?
C1 H1 0.94(2) . ?
N1 C2 1.335(3) . ?
N1 H1A 0.84(3) . ?
C2 O2 1.233(3) . ?
C2 C3 1.506(3) . ?
C3 C4 1.386(3) . ?
C3 C8 1.390(3) . ?
C4 C5 1.379(3) . ?
C4 H4 0.93(3) . ?
C5 F5 1.359(3) . ?
C5 C6 1.366(4) . ?
C6 C7 1.371(4) . ?
C6 H6 0.93(3) . ?
C7 C8 1.391(3) . ?
C7 H7 0.93(4) . ?
C8 H8 0.98(3) . ?
C9 N9 1.439(3) . ?
C9 H9A 1.02(3) . ?
C9 H9B 1.00(3) . ?
N9 C10 1.380(3) . ?
N9 H9 0.89(3) . ?
C10 C15 1.396(3) . ?
C10 C11 1.401(4) . ?
C11 C12 1.383(4) . ?
C11 H11 0.95(3) . ?
C12 C13 1.385(4) . ?
C12 H12 1.01(3) . ?
C13 C14 1.381(4) . ?
C13 H13 1.01(3) . ?
C14 C15 1.392(3) . ?
C14 H14 0.93(3) . ?
C15 H15 0.98(3) . ?
C16 C18 1.530(3) . ?
C16 C17 1.531(3) . ?
C16 H16 0.97(2) . ?
C17 H17A 0.99(3) . ?
C17 H17B 1.01(3) . ?
C17 H17C 1.02(4) . ?
C18 H18A 0.96(3) . ?
C18 H18B 0.97(3) . ?
C18 H18C 0.98(3) . ?

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
N1 C1 C9 108.85(16) . . ?
N1 C1 C16 111.12(16) . . ?
C9 C1 C16 112.60(17) . . ?
N1 C1 H1 106.1(13) . . ?
C9 C1 H1 109.6(13) . . ?
C16 C1 H1 108.4(14) . . ?
C2 N1 C1 121.81(16) . . ?
C2 N1 H1A 118.8(17) . . ?
C1 N1 H1A 119.3(17) . . ?
O2 C2 N1 123.09(19) . . ?
O2 C2 C3 120.45(19) . . ?
N1 C2 C3 116.46(17) . . ?
C4 C3 C8 119.8(2) . . ?
C4 C3 C2 117.64(19) . . ?
C8 C3 C2 122.58(19) . . ?
C5 C4 C3 118.6(2) . . ?
C5 C4 H4 122.3(19) . . ?
C3 C4 H4 119.1(19) . . ?
F5 C5 C6 118.9(2) . . ?
F5 C5 C4 118.2(3) . . ?
C6 C5 C4 122.8(2) . . ?
C5 C6 C7 118.2(2) . . ?
C5 C6 H6 116(2) . . ?
C7 C6 H6 126(2) . . ?
C6 C7 C8 121.1(3) . . ?
C6 C7 H7 120(2) . . ?
C8 C7 H7 119(2) . . ?
C3 C8 C7 119.5(2) . . ?
C3 C8 H8 122.8(19) . . ?
C7 C8 H8 117.7(19) . . ?
N9 C9 C1 115.81(19) . . ?
N9 C9 H9A 110.3(15) . . ?
C1 C9 H9A 108.7(16) . . ?
N9 C9 H9B 105.5(16) . . ?
C1 C9 H9B 110.2(15) . . ?
H9A C9 H9B 106(2) . . ?
C10 N9 C9 124.58(19) . . ?
C10 N9 H9 118.8(18) . . ?
C9 N9 H9 116.6(18) . . ?
N9 C10 C15 123.3(2) . . ?
N9 C10 C11 118.4(2) . . ?
C15 C10 C11 118.3(2) . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 120.7(16) . . ?
C10 C11 H11 118.6(16) . . ?
C11 C12 C13 120.9(2) . . ?
C11 C12 H12 115.8(19) . . ?
C13 C12 H12 123.3(19) . . ?
C14 C13 C12 118.9(2) . . ?
C14 C13 H13 119.7(18) . . ?
C12 C13 H13 121.4(18) . . ?
C13 C14 C15 121.0(2) . . ?
C13 C14 H14 117.4(17) . . ?
C15 C14 H14 121.6(17) . . ?
C14 C15 C10 120.3(2) . . ?
C14 C15 H15 116.7(15) . . ?
C10 C15 H15 123.0(15) . . ?
C18 C16 C17 111.0(2) . . ?
C18 C16 C1 113.11(18) . . ?
C17 C16 C1 111.4(2) . . ?
C18 C16 H16 108.8(14) . . ?
C17 C16 H16 103.7(14) . . ?
C1 C16 H16 108.3(14) . . ?
C16 C17 H17A 109(2) . . ?
C16 C17 H17B 112.2(18) . . ?
H17A C17 H17B 106(3) . . ?
C16 C17 H17C 110(2) . . ?
H17A C17 H17C 108(3) . . ?
H17B C17 H17C 112(3) . . ?
C16 C18 H18A 113.7(17) . . ?
C16 C18 H18B 108.0(19) . . ?
H18A C18 H18B 107(3) . . ?
C16 C18 H18C 108(2) . . ?
H18A C18 H18C 109(3) . . ?
H18B C18 H18C 112(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C1 N1 C2 -152.69(19) . . . . ?
C16 C1 N1 C2 82.8(2) . . . . ?
C1 N1 C2 O2 1.4(3) . . . . ?
C1 N1 C2 C3 -178.94(17) . . . . ?
O2 C2 C3 C4 25.7(3) . . . . ?
N1 C2 C3 C4 -154.0(2) . . . . ?
O2 C2 C3 C8 -153.5(2) . . . . ?
N1 C2 C3 C8 26.8(3) . . . . ?
C8 C3 C4 C5 -1.2(3) . . . . ?
C2 C3 C4 C5 179.5(2) . . . . ?
C3 C4 C5 F5 -178.9(2) . . . . ?
C3 C4 C5 C6 1.0(4) . . . . ?
F5 C5 C6 C7 180.0(3) . . . . ?
C4 C5 C6 C7 0.1(4) . . . . ?
C5 C6 C7 C8 -1.0(4) . . . . ?
C4 C3 C8 C7 0.4(3) . . . . ?
C2 C3 C8 C7 179.6(2) . . . . ?
C6 C7 C8 C3 0.8(4) . . . . ?
N1 C1 C9 N9 55.6(2) . . . . ?
C16 C1 C9 N9 179.31(17) . . . . ?
C1 C9 N9 C10 75.7(3) . . . . ?
C9 N9 C10 C15 -2.8(3) . . . . ?
C9 N9 C10 C11 175.9(2) . . . . ?
N9 C10 C11 C12 -179.6(2) . . . . ?
C15 C10 C11 C12 -0.9(3) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
C11 C12 C13 C14 0.4(4) . . . . ?
C12 C13 C14 C15 -0.7(4) . . . . ?
C13 C14 C15 C10 0.2(3) . . . . ?
N9 C10 C15 C14 179.2(2) . . . . ?
C11 C10 C15 C14 0.6(3) . . . . ?
N1 C1 C16 C18 65.2(2) . . . . ?
C9 C1 C16 C18 -57.2(2) . . . . ?
N1 C1 C16 C17 -168.88(19) . . . . ?
C9 C1 C16 C17 68.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N9 H9 O2 0.89(3) 2.35(3) 3.034(3) 133(2) 1_655 yes
N1 H1A O2 0.84(3) 2.32(3) 3.117(2) 158(2) 1_655 yes
N1 H1A O2 0.84(3) 2.32(3) 3.117(2) 158(2) 1_655 yes
N1 H1A O2 0.84(3) 2.32(3) 3.117(2) 158(2) 1_655 yes
N1 H1A O2 0.84(3) 2.32(3) 3.117(2) 158(2) 1_655 yes
N9 H9 O2 0.89(3) 2.35(3) 3.034(3) 133(2) 1_655 yes

_refine_diff_density_max         0.227
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_JF3173FMI
_database_code_depnum_ccdc_archive 'CCDC 2289936'
loop_
_audit_author_name
_audit_author_address
'James C. Fettinger'
;University of California, Davis
United States of America
;
_audit_update_record             
;
2023-08-21 deposited with the CCDC.	2025-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H19 F N2'
_chemical_formula_sum            'C18 H19 F N2'
_chemical_formula_weight         282.35

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'
N N 0.0061 0.0033 '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'

_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                   11.6012(2)
_cell_length_b                   14.6138(3)
_cell_length_c                   17.9894(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3049.88(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    9083
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      27.50

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.872
_exptl_crystal_size_mid          0.557
_exptl_crystal_size_min          0.462
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8900
_exptl_absorpt_correction_T_max  0.9632
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25518
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.795
_diffrn_reflns_theta_max         27.556
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7028
_reflns_number_gt                6516
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'Apex3 (2019.1) (Bruker, 2019)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    
'SHELXT (Sheldrick, 2015) Acta Cryst., A71, 3-8'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;

25 January, 2023
JF3173 APEX2 Mo  (YPC-4-4)

A colorless block with approximate orthogonal dimensions 0.462 x 0.557
x 0.872mm3, crystals shatter when cut, was placed and optically
centered on the Bruker Duo(1) APEXII CCD system at â\/E?83Â°C(190K).
Indexing of the unit cell used a random set of reflections collected
from three series of 0.5Â° wide omega-scans, 10 seconds per frame, and 30
frames per series that were well distributed in reciprocal space.
Seven omega-scan data frame series were collected [MoKa] with 0.3Â° wide
scans, 15 seconds per frame and 606 frames collected per series at
varying phi angles and plus/minus 32 degrees for the detector. The
crystal to detector distance was 5.15cm, thus providing a complete
sphere of data to 2thetamax=55.11Â°.

Structural determination and Refinement:

All crystallographic calculations were performed on a Surface Pro7
with Intel i7-1065G7 at 1.30GHz with four cores, eight processors and
16GB of extended memory. Data collected were corrected for Lorentz and
polarization effects with Saint(1) and absorption using Blessingâ\/E?s
method and merged as incorporated with the program Sadabs(2,3). The
SHELXTL(4) program package was implemented to determine the probable
space group and set up the initial files. System symmetry, systematic
absences and intensity statistics indicated the non-centrosymmetric
orthorhombic space group P212121 (no. 19). The structure was
determined by direct methods with the molecule being located using the
program XT(5). The structure was refined with XL(6). The 50305 data
collected were merged based upon identical indices to 25518, then
merged for least squares refinement to 7028 unique data
[R(int)=0.0215]. All full occupancy non-hydrogen atoms were refined
anisotropically. Two disorders were found in the fluorinated rings of
the two molecules and these were optimized to 0.95:0.05 and 0.82:0.18,
respectively.  Hydrogen atoms were idealized and those fully occupied
had their thermal parameters refined during the final refinement
stages. The final structure was refined to convergence with
R(F)=3.58%, wR(F2)=7.98%, GOF=1.016 for all 7028 unique reflections
[R(F)=3.19%, wR(F2)=7.72% for those 6516 data with Fo > 4?(Fo)]. The
final difference-Fourier map was featureless indicating that the
structure is both correct and complete. An empirical correction for
extinction was also attempted and found to be negative and therefore
not applied.  The structureâ\/E?s absolute structure parameters were
determined to be: Flack(x)(7), 0.04(19); Hooft(y)(8), 0.07(17) and the
Parsons(z)(6), 0.04(18) indicating that the structureâ\/E?s absolute
configuration has been determined reliably; these values would be
close to 1.0 if the structure were inverted.


References:

1.	Bruker (2019) APEXII (Version 2019.0) and (2016) SAINT (Version
8.37a). Bruker AXS Inc., Madison, Wisconsin, USA.

2.	An Empirical Correction for Absorption Anisotropy, Blessing, R. H.
(1995). Acta Cryst., A51, 33-38.

3.	Sheldrick, G.M., SADABS (2016) Version 2016/2, â\/E?Siemens Area
Detector Absorption Correctionâ\/E? UniversitÃ?t GÃ?ttingen: GÃ?ttingen,
Germany.

4.	Sheldrick, G.M., (2002). SHELXTL. Version 6.1. Bruker AXS Inc.,
Madison, Wisconsin, USA.

5.	Sheldrick, G. M., (2014) SHELXT, UniversitÃ?t GÃ?ttingen: GÃ?ttingen,
Germany.  Structure determination program. Private communication.

6.	Sheldrick, G. M., (2018). SHELXL2018/3. UniversitÃ?t GÃ?ttingen:
GÃ?ttingen, Germany.

7.	On Enantiomorph-Polarity Estimation, Flack, H.D. (1983). Acta
Cryst., A39, 876-881.

8.	Hooft, R.W.W, Straver, L.H. & Spek, A.L. (2008). J. Appl, Cryst.
41, 96-103. Thompson,A.L. & Watkin, D.J. (2009). Tetrahedron


Acknowledgment:  We thank the National Science Foundation (Grant CHE-
1531193) for the Dual Source X-ray actometer.

JC Fettinger, UC Davis


;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0387P)²+0.4136P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2674 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.04(19)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7028
_refine_ls_number_parameters     433
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0798
_refine_ls_wR_factor_gt          0.0772
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.11878(14) 0.67654(10) 0.28862(9) 0.0287(3) Uani 1 1 d . . . . .
N1 N 0.06721(13) 0.75891(9) 0.26929(8) 0.0340(3) Uani 1 1 d . . . . .
C2 C 0.23769(15) 0.73334(11) 0.20301(9) 0.0312(3) Uani 1 1 d . . . . .
H2 H 0.302079 0.769633 0.225296 0.028(4) Uiso 1 1 calc R . . . .
N2 N 0.21088(12) 0.65585(9) 0.25322(8) 0.0309(3) Uani 1 1 d . . . . .
C3 C 0.12832(16) 0.79251(12) 0.20319(10) 0.0355(4) Uani 1 1 d . . . . .
H3A H 0.147280 0.858308 0.207838 0.036(5) Uiso 1 1 calc R . . . .
H3B H 0.082282 0.782816 0.157524 0.042(5) Uiso 1 1 calc R . . . .
C4 C 0.06629(15) 0.61039(10) 0.34126(9) 0.0292(3) Uani 1 1 d . . . . .
C5 C -0.05272(15) 0.59816(11) 0.34516(9) 0.0320(3) Uani 1 1 d . . . . .
H5 H -0.103398 0.635583 0.316940 0.036(5) Uiso 1 1 calc R . . . .
C6 C -0.09512(16) 0.53031(12) 0.39106(9) 0.0376(4) Uani 1 1 d D . . . .
F6 F -0.20791(12) 0.51607(10) 0.39419(9) 0.0513(4) Uani 0.82 1 d D . P A 1
H6 H -0.176(3) 0.537(8) 0.382(6) 0.062 Uiso 0.18 1 d D U P B 2
C7 C -0.02544(18) 0.47552(12) 0.43394(10) 0.0403(4) Uani 1 1 d . . . . .
H7 H -0.057192 0.430017 0.465604 0.045(6) Uiso 1 1 calc R . . . .
C8 C 0.09220(18) 0.48875(13) 0.42949(10) 0.0407(4) Uani 1 1 d D . . . .
H8 H 0.142023 0.451725 0.458666 0.049 Uiso 0.82 1 calc R U P C 1
F8 F 0.1476(7) 0.4384(5) 0.4727(4) 0.068(2) Uiso 0.18 1 d D . P D 2
C9 C 0.13896(16) 0.55475(12) 0.38346(10) 0.0352(4) Uani 1 1 d . . . . .
H9 H 0.220187 0.562213 0.380559 0.032(5) Uiso 1 1 calc R . . . .
C10 C -0.00909(14) 0.81463(10) 0.30986(9) 0.0308(3) Uani 1 1 d . . . . .
C11 C -0.01787(16) 0.80984(11) 0.38687(10) 0.0347(4) Uani 1 1 d . . . . .
H11 H 0.026812 0.766501 0.413684 0.041(5) Uiso 1 1 calc R . . . .
C12 C -0.09167(17) 0.86816(12) 0.42452(11) 0.0409(4) Uani 1 1 d . . . . .
H12 H -0.098794 0.863471 0.476992 0.047(6) Uiso 1 1 calc R . . . .
C13 C -0.15516(17) 0.93323(12) 0.38640(12) 0.0419(4) Uani 1 1 d . . . . .
H13 H -0.204659 0.973715 0.412632 0.056(7) Uiso 1 1 calc R . . . .
C14 C -0.14608(17) 0.93889(12) 0.31008(12) 0.0418(4) Uani 1 1 d . . . . .
H14 H -0.189406 0.983513 0.283736 0.054(6) Uiso 1 1 calc R . . . .
C15 C -0.07432(16) 0.88002(12) 0.27176(11) 0.0380(4) Uani 1 1 d . . . . .
H15 H -0.069239 0.883994 0.219150 0.044(6) Uiso 1 1 calc R . . . .
C16 C 0.27552(15) 0.69966(12) 0.12659(9) 0.0346(4) Uani 1 1 d . . . . .
H16 H 0.212560 0.660869 0.105415 0.030(5) Uiso 1 1 calc R . . . .
C17 C 0.38417(18) 0.64130(16) 0.13322(12) 0.0502(5) Uani 1 1 d . . . . .
H17A H 0.404725 0.616959 0.084225 0.064(7) Uiso 1 1 calc R . . . .
H17B H 0.369937 0.590508 0.167584 0.063(7) Uiso 1 1 calc R . . . .
H17C H 0.447613 0.678981 0.152124 0.061(7) Uiso 1 1 calc R . . . .
C18 C 0.2960(2) 0.78016(15) 0.07426(11) 0.0502(5) Uani 1 1 d . . . . .
H18A H 0.353385 0.821428 0.096087 0.062(7) Uiso 1 1 calc R . . . .
H18B H 0.223571 0.813351 0.066719 0.069(8) Uiso 1 1 calc R . . . .
H18C H 0.324333 0.757432 0.026372 0.062(7) Uiso 1 1 calc R . . . .
C21 C 0.61064(14) 0.62228(11) 0.28428(9) 0.0298(3) Uani 1 1 d . . . . .
N21 N 0.55864(12) 0.53866(9) 0.26865(8) 0.0323(3) Uani 1 1 d . . . . .
C22 C 0.69650(15) 0.57945(11) 0.17926(10) 0.0331(4) Uani 1 1 d . . . . .
H22 H 0.657262 0.606605 0.134949 0.031(5) Uiso 1 1 calc R . . . .
N22 N 0.69111(13) 0.64771(9) 0.23981(8) 0.0336(3) Uani 1 1 d . . . . .
C23 C 0.62245(17) 0.49868(13) 0.20606(11) 0.0408(4) Uani 1 1 d . . . . .
H23A H 0.569482 0.477401 0.166533 0.060(7) Uiso 1 1 calc R . . . .
H23B H 0.671112 0.446844 0.222518 0.049(6) Uiso 1 1 calc R . . . .
C24 C 0.56481(15) 0.68547(10) 0.34161(9) 0.0302(3) Uani 1 1 d . . . . .
C25 C 0.44597(15) 0.69372(11) 0.35067(9) 0.0329(3) Uani 1 1 d D . . . .
H25 H 0.394177 0.656137 0.323448 0.035(5) Uiso 1 1 calc R . . . .
C26 C 0.40591(17) 0.75802(12) 0.40032(10) 0.0386(4) Uani 1 1 d D . . . .
F26 F 0.29045(11) 0.76534(9) 0.41018(8) 0.0577(4) Uani 0.95 1 d D . P E 1
H26 H 0.3241(12) 0.7638(8) 0.4068(6) 0.069 Uiso 0.05 1 d D U P F 2
C27 C 0.47702(19) 0.81408(12) 0.44090(10) 0.0437(5) Uani 1 1 d D . . . .
H27 H 0.446259 0.857887 0.474501 0.041(5) Uiso 1 1 calc R . . . .
C28 C 0.59428(19) 0.80495(14) 0.43147(11) 0.0468(5) Uani 1 1 d D . . . .
H28 H 0.645237 0.842369 0.459481 0.056 Uiso 0.95 1 calc R U P G 1
F28 F 0.672(5) 0.839(5) 0.480(3) 0.18(3) Uiso 0.05 1 d D . P H 2
C29 C 0.63901(17) 0.74171(13) 0.38150(11) 0.0407(4) Uani 1 1 d . . . . .
H29 H 0.719977 0.736948 0.374639 0.052(6) Uiso 1 1 calc R . . . .
C30 C 0.49787(14) 0.48108(10) 0.31838(10) 0.0310(3) Uani 1 1 d . . . . .
C31 C 0.50644(15) 0.48900(12) 0.39532(10) 0.0350(4) Uani 1 1 d . . . . .
H31 H 0.555058 0.534277 0.416595 0.027(4) Uiso 1 1 calc R . . . .
C32 C 0.44381(17) 0.43061(12) 0.44092(11) 0.0429(4) Uani 1 1 d . . . . .
H32 H 0.448343 0.437266 0.493374 0.049(6) Uiso 1 1 calc R . . . .
C33 C 0.37489(18) 0.36287(13) 0.41075(13) 0.0485(5) Uani 1 1 d . . . . .
H33 H 0.332423 0.323095 0.442290 0.057(7) Uiso 1 1 calc R . . . .
C34 C 0.36826(18) 0.35346(13) 0.33462(14) 0.0513(5) Uani 1 1 d . . . . .
H34 H 0.322092 0.306289 0.313792 0.067(7) Uiso 1 1 calc R . . . .
C35 C 0.42838(17) 0.41225(13) 0.28817(12) 0.0432(4) Uani 1 1 d . . . . .
H35 H 0.422364 0.405781 0.235766 0.052(6) Uiso 1 1 calc R . . . .
C36 C 0.81869(15) 0.55378(12) 0.15583(10) 0.0365(4) Uani 1 1 d . . . . .
H36 H 0.856076 0.519700 0.197571 0.042(5) Uiso 1 1 calc R . . . .
C37 C 0.89051(18) 0.63841(15) 0.13883(12) 0.0460(5) Uani 1 1 d . . . . .
H37A H 0.969135 0.619903 0.125764 0.064(7) Uiso 1 1 calc R . . . .
H37B H 0.892626 0.678145 0.182693 0.054(6) Uiso 1 1 calc R . . . .
H37C H 0.856005 0.671674 0.097086 0.053(6) Uiso 1 1 calc R . . . .
C38 C 0.8130(2) 0.49084(15) 0.08806(13) 0.0532(6) Uani 1 1 d . . . . .
H38A H 0.770703 0.435011 0.100983 0.066(7) Uiso 1 1 calc R . . . .
H38B H 0.891328 0.474797 0.072385 0.051(6) Uiso 1 1 calc R . . . .
H38C H 0.773291 0.522364 0.047360 0.080(9) Uiso 1 1 calc R . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.280(2) . ?
C1 N1 1.388(2) . ?
C1 C4 1.484(2) . ?
N1 C10 1.407(2) . ?
N1 C3 1.469(2) . ?
C2 N2 1.482(2) . ?
C2 C16 1.525(2) . ?
C2 C3 1.535(2) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.394(2) . ?
C4 C9 1.396(2) . ?
C5 C6 1.381(2) . ?
C5 H5 0.9500 . ?
C6 F6 1.326(2) . ?
C6 C7 1.375(3) . ?
C6 H6 0.961(14) . ?
C7 C8 1.381(3) . ?
C7 H7 0.9500 . ?
C8 F8 1.248(7) . ?
C8 C9 1.382(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.391(2) . ?
C10 C15 1.398(2) . ?
C11 C12 1.385(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C18 1.525(3) . ?
C16 C17 1.527(3) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C21 N22 1.284(2) . ?
C21 N21 1.392(2) . ?
C21 C24 1.483(2) . ?
N21 C30 1.416(2) . ?
N21 C23 1.469(2) . ?
C22 N22 1.478(2) . ?
C22 C36 1.526(2) . ?
C22 C23 1.537(2) . ?
C22 H22 1.0000 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C29 1.390(2) . ?
C24 C25 1.394(2) . ?
C25 C26 1.377(2) . ?
C25 H25 0.9500 . ?
C26 F26 1.355(2) . ?
C26 C27 1.373(3) . ?
C26 H26 0.960(14) . ?
C27 C28 1.377(3) . ?
C27 H27 0.9500 . ?
C28 F28 1.351(14) . ?
C28 C29 1.390(3) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 C31 1.393(2) . ?
C30 C35 1.399(2) . ?
C31 C32 1.389(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.383(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.379(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.387(3) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 C37 1.522(3) . ?
C36 C38 1.529(3) . ?
C36 H36 1.0000 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 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
N2 C1 N1 116.09(14) . . ?
N2 C1 C4 120.41(14) . . ?
N1 C1 C4 123.21(15) . . ?
C1 N1 C10 130.01(14) . . ?
C1 N1 C3 106.53(13) . . ?
C10 N1 C3 122.02(13) . . ?
N2 C2 C16 111.31(13) . . ?
N2 C2 C3 104.81(13) . . ?
C16 C2 C3 114.93(14) . . ?
N2 C2 H2 108.5 . . ?
C16 C2 H2 108.5 . . ?
C3 C2 H2 108.5 . . ?
C1 N2 C2 107.34(13) . . ?
N1 C3 C2 102.26(13) . . ?
N1 C3 H3A 111.3 . . ?
C2 C3 H3A 111.3 . . ?
N1 C3 H3B 111.3 . . ?
C2 C3 H3B 111.3 . . ?
H3A C3 H3B 109.2 . . ?
C5 C4 C9 119.75(16) . . ?
C5 C4 C1 121.47(14) . . ?
C9 C4 C1 118.60(15) . . ?
C6 C5 C4 118.36(16) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
F6 C6 C7 117.72(17) . . ?
F6 C6 C5 119.31(17) . . ?
C7 C6 C5 122.97(18) . . ?
C7 C6 H6 137(10) . . ?
C5 C6 H6 100(10) . . ?
C6 C7 C8 117.85(17) . . ?
C6 C7 H7 121.1 . . ?
C8 C7 H7 121.1 . . ?
F8 C8 C7 113.0(4) . . ?
F8 C8 C9 125.6(4) . . ?
C7 C8 C9 121.37(17) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C4 119.68(17) . . ?
C8 C9 H9 120.2 . . ?
C4 C9 H9 120.2 . . ?
C11 C10 C15 118.88(16) . . ?
C11 C10 N1 122.25(15) . . ?
C15 C10 N1 118.79(15) . . ?
C12 C11 C10 120.09(16) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 120.62(18) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 119.57(18) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 120.36(17) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 120.46(17) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C2 C16 C18 110.63(15) . . ?
C2 C16 C17 110.33(15) . . ?
C18 C16 C17 110.51(16) . . ?
C2 C16 H16 108.4 . . ?
C18 C16 H16 108.4 . . ?
C17 C16 H16 108.4 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N22 C21 N21 116.32(15) . . ?
N22 C21 C24 120.91(14) . . ?
N21 C21 C24 122.14(14) . . ?
C21 N21 C30 127.59(14) . . ?
C21 N21 C23 106.60(13) . . ?
C30 N21 C23 119.92(13) . . ?
N22 C22 C36 114.13(14) . . ?
N22 C22 C23 105.26(13) . . ?
C36 C22 C23 114.64(14) . . ?
N22 C22 H22 107.5 . . ?
C36 C22 H22 107.5 . . ?
C23 C22 H22 107.5 . . ?
C21 N22 C22 107.13(13) . . ?
N21 C23 C22 102.51(13) . . ?
N21 C23 H23A 111.3 . . ?
C22 C23 H23A 111.3 . . ?
N21 C23 H23B 111.3 . . ?
C22 C23 H23B 111.3 . . ?
H23A C23 H23B 109.2 . . ?
C29 C24 C25 120.08(16) . . ?
C29 C24 C21 120.35(16) . . ?
C25 C24 C21 119.34(15) . . ?
C26 C25 C24 117.95(16) . . ?
C26 C25 H25 121.0 . . ?
C24 C25 H25 121.0 . . ?
F26 C26 C27 118.50(17) . . ?
F26 C26 C25 118.18(17) . . ?
C27 C26 C25 123.32(18) . . ?
C27 C26 H26 118.5(7) . . ?
C25 C26 H26 118.1(7) . . ?
C26 C27 C28 118.05(17) . . ?
C26 C27 H27 121.0 . . ?
C28 C27 H27 121.0 . . ?
F28 C28 C27 123(3) . . ?
F28 C28 C29 114(3) . . ?
C27 C28 C29 120.86(18) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 H28 119.6 . . ?
C28 C29 C24 119.74(18) . . ?
C28 C29 H29 120.1 . . ?
C24 C29 H29 120.1 . . ?
C31 C30 C35 119.14(17) . . ?
C31 C30 N21 122.89(15) . . ?
C35 C30 N21 117.95(16) . . ?
C32 C31 C30 119.92(17) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C33 C32 C31 120.68(19) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C34 C33 C32 119.56(18) . . ?
C34 C33 H33 120.2 . . ?
C32 C33 H33 120.2 . . ?
C33 C34 C35 120.58(19) . . ?
C33 C34 H34 119.7 . . ?
C35 C34 H34 119.7 . . ?
C34 C35 C30 120.08(19) . . ?
C34 C35 H35 120.0 . . ?
C30 C35 H35 120.0 . . ?
C37 C36 C22 111.36(15) . . ?
C37 C36 C38 110.63(16) . . ?
C22 C36 C38 109.16(15) . . ?
C37 C36 H36 108.5 . . ?
C22 C36 H36 108.5 . . ?
C38 C36 H36 108.5 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 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
N2 C1 N1 C10 -157.87(17) . . . . ?
C4 C1 N1 C10 28.3(3) . . . . ?
N2 C1 N1 C3 8.4(2) . . . . ?
C4 C1 N1 C3 -165.51(15) . . . . ?
N1 C1 N2 C2 3.18(19) . . . . ?
C4 C1 N2 C2 177.23(14) . . . . ?
C16 C2 N2 C1 -137.60(15) . . . . ?
C3 C2 N2 C1 -12.77(17) . . . . ?
C1 N1 C3 C2 -15.17(17) . . . . ?
C10 N1 C3 C2 152.41(15) . . . . ?
N2 C2 C3 N1 16.75(17) . . . . ?
C16 C2 C3 N1 139.26(14) . . . . ?
N2 C1 C4 C5 -139.25(17) . . . . ?
N1 C1 C4 C5 34.4(2) . . . . ?
N2 C1 C4 C9 35.9(2) . . . . ?
N1 C1 C4 C9 -150.50(16) . . . . ?
C9 C4 C5 C6 -0.2(2) . . . . ?
C1 C4 C5 C6 174.86(14) . . . . ?
C4 C5 C6 F6 -178.36(16) . . . . ?
C4 C5 C6 C7 1.2(2) . . . . ?
F6 C6 C7 C8 178.52(18) . . . . ?
C5 C6 C7 C8 -1.0(2) . . . . ?
C6 C7 C8 F8 177.2(4) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
F8 C8 C9 C4 -175.9(5) . . . . ?
C7 C8 C9 C4 1.0(3) . . . . ?
C5 C4 C9 C8 -0.8(3) . . . . ?
C1 C4 C9 C8 -176.04(16) . . . . ?
C1 N1 C10 C11 21.0(3) . . . . ?
C3 N1 C10 C11 -143.39(17) . . . . ?
C1 N1 C10 C15 -162.09(17) . . . . ?
C3 N1 C10 C15 33.5(2) . . . . ?
C15 C10 C11 C12 1.1(3) . . . . ?
N1 C10 C11 C12 177.97(16) . . . . ?
C10 C11 C12 C13 -1.6(3) . . . . ?
C11 C12 C13 C14 1.1(3) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C14 C15 C10 -0.7(3) . . . . ?
C11 C10 C15 C14 0.1(3) . . . . ?
N1 C10 C15 C14 -176.93(16) . . . . ?
N2 C2 C16 C18 176.71(15) . . . . ?
C3 C2 C16 C18 57.8(2) . . . . ?
N2 C2 C16 C17 -60.70(19) . . . . ?
C3 C2 C16 C17 -179.63(15) . . . . ?
N22 C21 N21 C30 157.63(16) . . . . ?
C24 C21 N21 C30 -31.5(2) . . . . ?
N22 C21 N21 C23 5.2(2) . . . . ?
C24 C21 N21 C23 176.11(15) . . . . ?
N21 C21 N22 C22 4.75(19) . . . . ?
C24 C21 N22 C22 -166.27(14) . . . . ?
C36 C22 N22 C21 -138.76(15) . . . . ?
C23 C22 N22 C21 -12.19(18) . . . . ?
C21 N21 C23 C22 -12.04(18) . . . . ?
C30 N21 C23 C22 -167.00(15) . . . . ?
N22 C22 C23 N21 14.54(18) . . . . ?
C36 C22 C23 N21 140.80(15) . . . . ?
N22 C21 C24 C29 -40.9(2) . . . . ?
N21 C21 C24 C29 148.56(17) . . . . ?
N22 C21 C24 C25 133.55(17) . . . . ?
N21 C21 C24 C25 -36.9(2) . . . . ?
C29 C24 C25 C26 -0.6(2) . . . . ?
C21 C24 C25 C26 -175.10(14) . . . . ?
C24 C25 C26 F26 -179.01(16) . . . . ?
C24 C25 C26 C27 0.1(2) . . . . ?
F26 C26 C27 C28 178.84(17) . . . . ?
C25 C26 C27 C28 -0.3(3) . . . . ?
C26 C27 C28 F28 -163(4) . . . . ?
C26 C27 C28 C29 0.9(3) . . . . ?
F28 C28 C29 C24 164(3) . . . . ?
C27 C28 C29 C24 -1.4(3) . . . . ?
C25 C24 C29 C28 1.2(3) . . . . ?
C21 C24 C29 C28 175.68(17) . . . . ?
C21 N21 C30 C31 -17.1(3) . . . . ?
C23 N21 C30 C31 132.12(18) . . . . ?
C21 N21 C30 C35 164.30(16) . . . . ?
C23 N21 C30 C35 -46.5(2) . . . . ?
C35 C30 C31 C32 -1.8(3) . . . . ?
N21 C30 C31 C32 179.58(15) . . . . ?
C30 C31 C32 C33 1.6(3) . . . . ?
C31 C32 C33 C34 -0.1(3) . . . . ?
C32 C33 C34 C35 -1.1(3) . . . . ?
C33 C34 C35 C30 0.9(3) . . . . ?
C31 C30 C35 C34 0.6(3) . . . . ?
N21 C30 C35 C34 179.24(17) . . . . ?
N22 C22 C36 C37 -51.8(2) . . . . ?
C23 C22 C36 C37 -173.30(16) . . . . ?
N22 C22 C36 C38 -174.21(15) . . . . ?
C23 C22 C36 C38 64.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C25 H25 N2 0.95 2.47 3.289(2) 143.9 . yes

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.026

####################################################################### 
# 
# 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_JF3154FMI
_database_code_depnum_ccdc_archive 'CCDC 2289935'
loop_
_audit_author_name
_audit_author_address
'James C. Fettinger'
;University of California, Davis
United States of America
;
_audit_update_record             
;
2023-08-21 deposited with the CCDC.	2025-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H37 F N2 O2 Si'
_chemical_formula_sum            'C25 H37 F N2 O2 Si'
_chemical_formula_weight         444.65

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

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

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

_cell_length_a                   10.4984(6)
_cell_length_b                   23.5281(13)
_cell_length_c                   11.1188(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.2216(12)
_cell_angle_gamma                90
_cell_volume                     2593.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      27.35

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.249
_exptl_crystal_size_min          0.196
_exptl_absorpt_coefficient_mu    0.120
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9363
_exptl_absorpt_correction_T_max  0.9745
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Photon2 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23292
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.229
_diffrn_reflns_theta_max         27.463
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             11858
_reflns_number_gt                10811
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.948
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.995

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

_computing_data_collection       'Apex3 (2019.11-0) (Bruker, 2019)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;14 September, 2022 JF3154 Kappa Venture 190K

A colorless block with approximate orthogonal dimensions 0.196 x 0.249
x 0.269mm3 was placed and optically centered on the Bruker(1) Venture
Dual source Kappa diffractometer with Photon2 CMOS detector at
â\/E?93Â°C(190K).  Indexing of the unit cell used a random set of
reflections collected from three series of 0.5Â° wide omega-scans, 5
seconds per frame, and 30 frames per series that were well distributed
in reciprocal space. Data were collected [MoKa] with 0.3Â° wide scans,
variable time per frame dependent upon detector 2theta angle and
varying phi and omega angles such that nearly all unique reflections
were collected at least once.  The crystal to detector distance was
65.00mm, thus providing a complete sphere of data to 2thetamax=54.99Â°.

Structural determination and Refinement:

All crystallographic calculations were performed on a Surface Pro7
with Intel i7-1065G7 at 1.30GHz with four cores, eight processors and
16GB of extended memory. Data collected were corrected for Lorentz and
polarization effects with Saint(1) and absorption using Blessingâ\/E?s
method and merged as incorporated with the program Sadabs(2,3). The
SHELXTL4 program package was implemented to determine the probable
space group and set up the initial files. System symmetry, systematic
absences and intensity statistics indicated the non-centrosymmetric
monoclinic space group P21 (no. 4). The structure was determined by
direct methods with the non-hydrogen atoms being located directly for
the molecule using the program XT(5). The structure was refined with
XL(6). The 59107 data collected were merged, based upon identical
indices to 23292 data, then for least squares refinement to 11858
unique data [R(int)=0.0155]. One t-butyl ligand was found to be
disordered, modeled and found to be present in two orientations,
0.50:0.50. All non-hydrogen atoms were refined anisotropically.
Hydrogen atoms were initially idealized, then their thermal parameters
allowed to refine throughout the final refinement stage. The final
structure was refined to convergence with R(F)=3.97%, wR(F2)=8.60%,
GOF=1.038 for all 11858 unique reflections [R(F)=3.44%, wR(F2)=8.29%
for those 10811 data with Fo > 4?(Fo)]. The final difference-Fourier
map was featureless indicating that the structure is both correct and
complete.  An empirical correction for extinction was also attempted
and found to be negative and therefore not applied.  The absolute
structure parameters were determined to be: Flack(x)(7), 0.009(16);
Hooft(y)(8), -0.001(17) and the Parsons(z)(6), -0.001(14) indicating
that the structureâ\/E?s absolute configuration has been determined
reliably; these values would be close to 1.0 if the structure were
inverted.

References:

1.	Bruker (2019) APEX3 (Version 2019.0) and (2016) SAINT (Version
8.37a). Bruker AXS Inc., Madison, Wisconsin, USA. 2.	An Empirical
Correction for Absorption Anisotropy, Blessing, R. H. (1995). Acta
Cryst., A51, 33-38.

3.	Sheldrick, G.M., SADABS (2016) Version 2016/2, â\/E?Siemens Area
Detector Absorption Correctionâ\/E? UniversitÃ?t GÃ?ttingen: GÃ?ttingen,
Germany.

4.	Sheldrick, G.M., (2002). SHELXTL. Version 6.1. Bruker AXS Inc.,
Madison, Wisconsin, USA.

5.	Sheldrick, G. M., (2014) SHELXT, UniversitÃ?t GÃ?ttingen: GÃ?ttingen,
Germany.  Structure determination program. Private communication.

6.	Sheldrick, G. M., (2017). SHELXL2017/1. UniversitÃ?t GÃ?ttingen:
GÃ?ttingen, Germany.

7.	On Enantiomorph-Polarity Estimation, Flack, H.D. (1983). Acta
Cryst., A39, 876-881.

8.	Hooft, R.W.W, Straver, L.H. & Spek, A.L. (2008). J. Appl, Cryst.
41, 96-103. Thompson,A.L. & Watkin, D.J. (2009). Tetrahedron

Acknowledgment:  We thank the National Science Foundation (Grant CHE-
1531193) for the Dual Source X-ray diffractometer.,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)+(0.0420P)²+0.4751P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 4855 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.009(16)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         11858
_refine_ls_number_parameters     679
_refine_ls_number_restraints     39
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0860
_refine_ls_wR_factor_gt          0.0829
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.36210(6) 0.63381(3) 0.52659(6) 0.02904(13) Uani 1 1 d . . . . .
C1 C 0.3684(3) 0.70221(10) 0.4425(2) 0.0390(5) Uani 1 1 d . . . . .
H1 H 0.454214 0.701815 0.421974 0.071(11) Uiso 1 1 calc R . . . .
O1 O 0.38870(17) 0.58348(7) 0.43596(16) 0.0334(3) Uani 1 1 d . . . . .
H1A H 0.393212 0.551966 0.472642 0.096(15) Uiso 1 1 calc R . . . .
C2 C 0.2533(3) 0.70934(11) 0.3158(3) 0.0466(6) Uani 1 1 d . . . . .
H2A H 0.166674 0.709043 0.331354 0.068(11) Uiso 1 1 calc R . . . .
H2B H 0.255726 0.677998 0.258554 0.056(9) Uiso 1 1 calc R . . . .
H2C H 0.263943 0.745535 0.276546 0.059(9) Uiso 1 1 calc R . . . .
C3 C 0.3733(4) 0.75489(12) 0.5247(3) 0.0644(10) Uani 1 1 d . . . . .
H3A H 0.377354 0.789105 0.475805 0.079(11) Uiso 1 1 calc R . . . .
H3B H 0.453403 0.753116 0.601029 0.066(10) Uiso 1 1 calc R . . . .
H3C H 0.292136 0.756171 0.549747 0.089(14) Uiso 1 1 calc R . . . .
C4 C 0.4940(2) 0.63193(12) 0.6877(2) 0.0396(5) Uani 1 1 d . . . . .
H4 H 0.482594 0.666561 0.735307 0.046(8) Uiso 1 1 calc R . . . .
C5 C 0.4831(3) 0.57985(13) 0.7659(3) 0.0465(6) Uani 1 1 d . . . . .
H5A H 0.494340 0.545278 0.721305 0.049(8) Uiso 1 1 calc R . . . .
H5B H 0.394386 0.579413 0.777166 0.057(9) Uiso 1 1 calc R . . . .
H5C H 0.553704 0.581483 0.849511 0.085(12) Uiso 1 1 calc R . . . .
C6 C 0.6346(3) 0.6348(2) 0.6729(4) 0.0748(12) Uani 1 1 d . . . . .
H6A H 0.703656 0.636957 0.757213 0.073(10) Uiso 1 1 calc R . . . .
H6B H 0.640194 0.668557 0.623278 0.081(12) Uiso 1 1 calc R . . . .
H6C H 0.649295 0.600658 0.628659 0.094(17) Uiso 1 1 calc R . . . .
C7 C 0.1868(2) 0.62346(9) 0.5381(2) 0.0310(5) Uani 1 1 d . . . . .
C8 C 0.1473(3) 0.65173(11) 0.6291(2) 0.0383(5) Uani 1 1 d . . . . .
F8 F 0.23771(17) 0.68881(8) 0.70720(16) 0.0550(4) Uani 1 1 d . . . . .
C9 C 0.0257(3) 0.64637(14) 0.6487(3) 0.0503(7) Uani 1 1 d . . . . .
H9 H 0.006458 0.667078 0.714022 0.061(10) Uiso 1 1 calc R . . . .
C10 C -0.0674(3) 0.60990(15) 0.5703(3) 0.0598(8) Uani 1 1 d . . . . .
H10 H -0.152804 0.604950 0.581005 0.067(10) Uiso 1 1 calc R . . . .
C11 C -0.0368(3) 0.58062(14) 0.4764(3) 0.0510(7) Uani 1 1 d . . . . .
H11 H -0.102129 0.555889 0.421912 0.063(10) Uiso 1 1 calc R . . . .
C12 C 0.0883(2) 0.58655(10) 0.4597(2) 0.0333(5) Uani 1 1 d . . . . .
C13 C 0.1115(2) 0.54963(10) 0.3581(2) 0.0324(5) Uani 1 1 d . . . . .
N13 N 0.0920(2) 0.57406(10) 0.2451(2) 0.0358(4) Uani 1 1 d . . . . .
H13 H 0.075(3) 0.6063(12) 0.240(2) 0.026(6) Uiso 1 1 d . . . . .
O13 O 0.1384(2) 0.49922(8) 0.37755(18) 0.0457(4) Uani 1 1 d . . . . .
C14 C 0.1063(2) 0.54409(12) 0.1341(2) 0.0406(6) Uani 1 1 d D . . . .
H14 H 0.152511 0.506757 0.160660 0.071(11) Uiso 1 1 calc R . . A 1
C15 C 0.1889(3) 0.58172(13) 0.0749(2) 0.0433(6) Uani 1 1 d . . . . .
H15A H 0.186011 0.565685 -0.008255 0.036(7) Uiso 1 1 calc R . . . .
H15B H 0.148884 0.620252 0.059855 0.040(7) Uiso 1 1 calc R . . . .
N15 N 0.3269(2) 0.58544(10) 0.1576(2) 0.0404(5) Uani 1 1 d . . . . .
H15 H 0.342(3) 0.5812(14) 0.231(3) 0.044(9) Uiso 1 1 d . . . . .
C16 C 0.4174(3) 0.62266(10) 0.1315(2) 0.0391(5) Uani 1 1 d . . . . .
C17 C 0.3863(3) 0.65336(13) 0.0186(3) 0.0482(6) Uani 1 1 d . . . . .
H17 H 0.299407 0.650022 -0.043774 0.049(8) Uiso 1 1 calc R . . . .
C18 C 0.4824(4) 0.68898(15) -0.0030(3) 0.0601(8) Uani 1 1 d . . . . .
H18 H 0.460058 0.710023 -0.080057 0.063(10) Uiso 1 1 calc R . . . .
C19 C 0.6090(4) 0.69424(15) 0.0851(3) 0.0639(9) Uani 1 1 d . . . . .
H19 H 0.673949 0.718488 0.069144 0.109(16) Uiso 1 1 calc R . . . .
C20 C 0.6408(3) 0.66363(14) 0.1981(3) 0.0577(8) Uani 1 1 d . . . . .
H20 H 0.728321 0.666788 0.259424 0.067(11) Uiso 1 1 calc R . . . .
C21 C 0.5463(3) 0.62870(12) 0.2217(3) 0.0464(6) Uani 1 1 d . . . . .
H21 H 0.568809 0.608523 0.299928 0.046(8) Uiso 1 1 calc R . . . .
C22 C -0.0392(10) 0.5346(5) 0.0391(10) 0.055(3) Uani 0.5 1 d D U P B 1
C23 C -0.1101(15) 0.4917(7) 0.1016(15) 0.0747(16) Uani 0.5 1 d D . P B 1
H23A H -0.055988 0.456938 0.123895 0.112 Uiso 0.5 1 calc R U P B 1
H23B H -0.119659 0.508503 0.178851 0.112 Uiso 0.5 1 calc R U P B 1
H23C H -0.199520 0.482506 0.041687 0.112 Uiso 0.5 1 calc R U P B 1
C24 C -0.1224(10) 0.5887(5) 0.0042(9) 0.093(3) Uani 0.5 1 d D U P B 1
H24A H -0.127221 0.606947 0.081836 0.139 Uiso 0.5 1 calc R U P B 1
H24B H -0.079888 0.614762 -0.040058 0.139 Uiso 0.5 1 calc R U P B 1
H24C H -0.213611 0.579378 -0.051698 0.139 Uiso 0.5 1 calc R U P B 1
C25 C -0.0314(9) 0.5061(5) -0.0819(7) 0.086(3) Uani 0.5 1 d D U P B 1
H25A H 0.022213 0.471262 -0.059284 0.129 Uiso 0.5 1 calc R U P B 1
H25B H -0.122660 0.496745 -0.137858 0.129 Uiso 0.5 1 calc R U P B 1
H25C H 0.011063 0.532129 -0.126218 0.129 Uiso 0.5 1 calc R U P B 1
C22B C -0.0227(10) 0.5162(4) 0.0412(10) 0.049(2) Uani 0.5 1 d D U P B 2
C23B C -0.1025(15) 0.4872(7) 0.1161(15) 0.0747(16) Uani 0.5 1 d D . P B 2
H23D H -0.127838 0.515287 0.169207 0.112 Uiso 0.5 1 calc R U P B 2
H23E H -0.184096 0.469964 0.056839 0.112 Uiso 0.5 1 calc R U P B 2
H23F H -0.046820 0.457544 0.170546 0.112 Uiso 0.5 1 calc R U P B 2
C24B C -0.1080(9) 0.5637(4) -0.0421(9) 0.083(3) Uani 0.5 1 d D U P B 2
H24D H -0.131856 0.591661 0.012221 0.124 Uiso 0.5 1 calc R U P B 2
H24E H -0.056045 0.582308 -0.089734 0.124 Uiso 0.5 1 calc R U P B 2
H24F H -0.190485 0.547354 -0.101886 0.124 Uiso 0.5 1 calc R U P B 2
C25B C 0.0159(9) 0.4720(3) -0.0408(7) 0.067(2) Uani 0.5 1 d D U P B 2
H25D H 0.067284 0.490330 -0.089418 0.100 Uiso 0.5 1 calc R U P B 2
H25E H 0.071307 0.442441 0.013979 0.100 Uiso 0.5 1 calc R U P B 2
H25F H -0.065970 0.454861 -0.099727 0.100 Uiso 0.5 1 calc R U P B 2
Si31 Si 0.23451(6) 0.37217(3) 0.61869(6) 0.03092(13) Uani 1 1 d . . . . .
C31 C 0.1922(3) 0.29448(11) 0.6118(3) 0.0445(6) Uani 1 1 d . . . . .
H31 H 0.234762 0.278869 0.699582 0.062(10) Uiso 1 1 calc R . . . .
O31 O 0.19510(17) 0.39400(7) 0.47107(15) 0.0341(3) Uani 1 1 d . . . . .
H31A H 0.189200 0.429616 0.468920 0.052(9) Uiso 1 1 calc R . . . .
C32 C 0.2562(3) 0.26361(12) 0.5249(3) 0.0521(7) Uani 1 1 d . . . . .
H32A H 0.238819 0.222725 0.526316 0.075(11) Uiso 1 1 calc R . . . .
H32B H 0.353689 0.270401 0.554999 0.116(17) Uiso 1 1 calc R . . . .
H32C H 0.216938 0.277909 0.437665 0.071(11) Uiso 1 1 calc R . . . .
C33 C 0.0420(4) 0.28142(16) 0.5725(4) 0.0720(11) Uani 1 1 d . . . . .
H33A H -0.004771 0.299770 0.490701 0.089(15) Uiso 1 1 calc R . . . .
H33B H 0.005967 0.295873 0.637413 0.102(15) Uiso 1 1 calc R . . . .
H33C H 0.028271 0.240227 0.564001 0.101(15) Uiso 1 1 calc R . . . .
C34 C 0.1492(3) 0.41845(12) 0.7067(3) 0.0417(6) Uani 1 1 d . . . . .
H34 H 0.152340 0.399146 0.787768 0.041(7) Uiso 1 1 calc R . . . .
C35 C 0.2242(3) 0.47557(12) 0.7386(3) 0.0503(7) Uani 1 1 d . . . . .
H35A H 0.228722 0.493090 0.660140 0.052(9) Uiso 1 1 calc R . . . .
H35B H 0.315809 0.469096 0.797255 0.050(8) Uiso 1 1 calc R . . . .
H35C H 0.175873 0.500895 0.778704 0.090(13) Uiso 1 1 calc R . . . .
C36 C 0.0002(3) 0.42981(15) 0.6263(4) 0.0587(8) Uani 1 1 d . . . . .
H36A H -0.039722 0.456225 0.671997 0.080(12) Uiso 1 1 calc R . . . .
H36B H -0.050027 0.393935 0.611716 0.077(12) Uiso 1 1 calc R . . . .
H36C H -0.003947 0.446445 0.544300 0.13(2) Uiso 1 1 calc R . . . .
C37 C 0.4244(2) 0.37566(10) 0.6969(2) 0.0324(4) Uani 1 1 d . . . . .
C38 C 0.4831(3) 0.35372(11) 0.8185(2) 0.0400(5) Uani 1 1 d . . . . .
F38 F 0.39833(17) 0.33712(8) 0.88274(15) 0.0519(4) Uani 1 1 d . . . . .
C39 C 0.6190(3) 0.34749(13) 0.8812(3) 0.0472(6) Uani 1 1 d . . . . .
H39 H 0.651465 0.331040 0.963721 0.053(9) Uiso 1 1 calc R . . . .
C40 C 0.7069(3) 0.36595(13) 0.8202(3) 0.0461(6) Uani 1 1 d . . . . .
H40 H 0.801589 0.362476 0.860781 0.046(8) Uiso 1 1 calc R . . . .
C41 C 0.6562(2) 0.38952(11) 0.6995(3) 0.0393(5) Uani 1 1 d . . . . .
H41 H 0.716629 0.402398 0.657792 0.043(8) Uiso 1 1 calc R . . . .
C42 C 0.5176(2) 0.39453(9) 0.6388(2) 0.0307(4) Uani 1 1 d . . . . .
C43 C 0.4727(2) 0.42478(9) 0.5128(2) 0.0300(4) Uani 1 1 d . . . . .
N43 N 0.47898(19) 0.39498(9) 0.41210(19) 0.0309(4) Uani 1 1 d . . . . .
H43 H 0.500(3) 0.3622(13) 0.423(2) 0.028(7) Uiso 1 1 d . . . . .
O43 O 0.43847(19) 0.47465(7) 0.50697(18) 0.0420(4) Uani 1 1 d . . . . .
C44 C 0.4427(2) 0.41626(10) 0.2818(2) 0.0332(5) Uani 1 1 d . . . . .
H44 H 0.389929 0.452042 0.277154 0.033(6) Uiso 1 1 calc R . . . .
C45 C 0.3495(2) 0.37330(13) 0.1927(2) 0.0417(5) Uani 1 1 d . . . . .
H45A H 0.334096 0.384632 0.103262 0.046(8) Uiso 1 1 calc R . . . .
H45B H 0.393174 0.335455 0.206209 0.062(10) Uiso 1 1 calc R . . . .
N45 N 0.2215(2) 0.36976(12) 0.2148(2) 0.0458(5) Uani 1 1 d . . . . .
H45 H 0.227(3) 0.3754(14) 0.293(3) 0.046(8) Uiso 1 1 d . . . . .
C46 C 0.1250(3) 0.33092(12) 0.1502(2) 0.0400(5) Uani 1 1 d . . . . .
C47 C 0.1305(3) 0.30213(14) 0.0421(3) 0.0534(7) Uani 1 1 d . . . . .
H47 H 0.203900 0.308221 0.011517 0.066(10) Uiso 1 1 calc R . . . .
C48 C 0.0282(3) 0.26461(16) -0.0204(3) 0.0623(9) Uani 1 1 d . . . . .
H48 H 0.032741 0.245146 -0.093766 0.087(13) Uiso 1 1 calc R . . . .
C49 C -0.0798(3) 0.25485(14) 0.0212(3) 0.0587(8) Uani 1 1 d . . . . .
H49 H -0.149366 0.229219 -0.023117 0.095(14) Uiso 1 1 calc R . . . .
C50 C -0.0854(3) 0.28284(13) 0.1281(3) 0.0496(7) Uani 1 1 d . . . . .
H50 H -0.158569 0.275899 0.158509 0.071(11) Uiso 1 1 calc R . . . .
C51 C 0.0146(3) 0.32106(12) 0.1918(3) 0.0428(6) Uani 1 1 d . . . . .
H51 H 0.008267 0.340709 0.264293 0.041(7) Uiso 1 1 calc R . . . .
C52 C 0.5686(2) 0.43149(11) 0.2443(3) 0.0397(5) Uani 1 1 d . . . . .
C53 C 0.6547(3) 0.47388(15) 0.3419(3) 0.0552(8) Uani 1 1 d . . . . .
H53A H 0.600240 0.507322 0.345016 0.067(11) Uiso 1 1 calc R . . . .
H53B H 0.732108 0.485520 0.316978 0.072(11) Uiso 1 1 calc R . . . .
H53C H 0.686830 0.455928 0.426050 0.061(10) Uiso 1 1 calc R . . . .
C54 C 0.5218(3) 0.46055(14) 0.1131(3) 0.0512(7) Uani 1 1 d . . . . .
H54A H 0.462683 0.492609 0.114544 0.043(8) Uiso 1 1 calc R . . . .
H54B H 0.472239 0.433147 0.048150 0.077(12) Uiso 1 1 calc R . . . .
H54C H 0.600483 0.474393 0.093067 0.066(10) Uiso 1 1 calc R . . . .
C55 C 0.6531(3) 0.37888(14) 0.2416(3) 0.0554(8) Uani 1 1 d . . . . .
H55A H 0.733221 0.390208 0.220713 0.055(9) Uiso 1 1 calc R . . . .
H55B H 0.599268 0.352258 0.177014 0.074(12) Uiso 1 1 calc R . . . .
H55C H 0.681086 0.360457 0.325304 0.058(9) Uiso 1 1 calc R . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si1 O1 1.6374(17) . ?
Si1 C4 1.870(2) . ?
Si1 C1 1.873(3) . ?
Si1 C7 1.902(2) . ?
C1 C3 1.530(4) . ?
C1 C2 1.533(4) . ?
C1 H1 1.0000 . ?
O1 H1A 0.8400 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.529(4) . ?
C4 C6 1.539(4) . ?
C4 H4 1.0000 . ?
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 C8 1.383(3) . ?
C7 C12 1.411(3) . ?
C8 F8 1.369(3) . ?
C8 C9 1.370(4) . ?
C9 C10 1.375(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.374(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.507(3) . ?
C13 O13 1.222(3) . ?
C13 N13 1.335(3) . ?
N13 C14 1.471(3) . ?
N13 H13 0.78(3) . ?
C14 C15 1.531(4) . ?
C14 C22B 1.552(9) . ?
C14 C22 1.560(10) . ?
C14 H14 1.0000 . ?
C15 N15 1.441(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
N15 C16 1.391(3) . ?
N15 H15 0.78(3) . ?
C16 C17 1.391(4) . ?
C16 C21 1.401(4) . ?
C17 C18 1.393(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.372(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.389(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.378(4) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C24 1.520(10) . ?
C22 C25 1.529(10) . ?
C22 C23 1.549(10) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C22B C25B 1.523(10) . ?
C22B C23B 1.524(10) . ?
C22B C24B 1.536(10) . ?
C23B H23D 0.9800 . ?
C23B H23E 0.9800 . ?
C23B H23F 0.9800 . ?
C24B H24D 0.9800 . ?
C24B H24E 0.9800 . ?
C24B H24F 0.9800 . ?
C25B H25D 0.9800 . ?
C25B H25E 0.9800 . ?
C25B H25F 0.9800 . ?
Si31 O31 1.6377(18) . ?
Si31 C31 1.877(3) . ?
Si31 C34 1.877(3) . ?
Si31 C37 1.896(2) . ?
C31 C33 1.522(4) . ?
C31 C32 1.530(4) . ?
C31 H31 1.0000 . ?
O31 H31A 0.8400 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 C35 1.539(4) . ?
C34 C36 1.548(4) . ?
C34 H34 1.0000 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 C38 1.388(3) . ?
C37 C42 1.410(3) . ?
C38 F38 1.368(3) . ?
C38 C39 1.374(4) . ?
C39 C40 1.384(4) . ?
C39 H39 0.9500 . ?
C40 C41 1.386(4) . ?
C40 H40 0.9500 . ?
C41 C42 1.393(3) . ?
C41 H41 0.9500 . ?
C42 C43 1.502(3) . ?
C43 O43 1.223(3) . ?
C43 N43 1.341(3) . ?
N43 C44 1.460(3) . ?
N43 H43 0.80(3) . ?
C44 C45 1.524(3) . ?
C44 C52 1.552(3) . ?
C44 H44 1.0000 . ?
C45 N45 1.446(3) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
N45 C46 1.378(3) . ?
N45 H45 0.86(3) . ?
C46 C47 1.397(4) . ?
C46 C51 1.402(4) . ?
C47 C48 1.387(4) . ?
C47 H47 0.9500 . ?
C48 C49 1.378(5) . ?
C48 H48 0.9500 . ?
C49 C50 1.376(5) . ?
C49 H49 0.9500 . ?
C50 C51 1.387(4) . ?
C50 H50 0.9500 . ?
C51 H51 0.9500 . ?
C52 C55 1.529(4) . ?
C52 C53 1.530(4) . ?
C52 C54 1.538(4) . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C55 H55A 0.9800 . ?
C55 H55B 0.9800 . ?
C55 H55C 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
O1 Si1 C4 110.48(11) . . ?
O1 Si1 C1 105.84(10) . . ?
C4 Si1 C1 111.22(12) . . ?
O1 Si1 C7 108.28(9) . . ?
C4 Si1 C7 111.13(10) . . ?
C1 Si1 C7 109.71(11) . . ?
C3 C1 C2 108.7(2) . . ?
C3 C1 Si1 113.42(19) . . ?
C2 C1 Si1 113.96(18) . . ?
C3 C1 H1 106.7 . . ?
C2 C1 H1 106.7 . . ?
Si1 C1 H1 106.7 . . ?
Si1 O1 H1A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C6 110.5(2) . . ?
C5 C4 Si1 113.18(18) . . ?
C6 C4 Si1 109.27(19) . . ?
C5 C4 H4 107.9 . . ?
C6 C4 H4 107.9 . . ?
Si1 C4 H4 107.9 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 114.4(2) . . ?
C8 C7 Si1 121.15(18) . . ?
C12 C7 Si1 124.47(17) . . ?
F8 C8 C9 116.4(2) . . ?
F8 C8 C7 117.3(2) . . ?
C9 C8 C7 126.3(2) . . ?
C8 C9 C10 117.5(3) . . ?
C8 C9 H9 121.3 . . ?
C10 C9 H9 121.3 . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 121.2(3) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C7 120.7(2) . . ?
C11 C12 C13 115.7(2) . . ?
C7 C12 C13 123.5(2) . . ?
O13 C13 N13 122.7(2) . . ?
O13 C13 C12 120.8(2) . . ?
N13 C13 C12 116.4(2) . . ?
C13 N13 C14 123.8(2) . . ?
C13 N13 H13 116.8(19) . . ?
C14 N13 H13 119.3(19) . . ?
N13 C14 C15 108.1(2) . . ?
N13 C14 C22B 117.0(4) . . ?
C15 C14 C22B 116.9(5) . . ?
N13 C14 C22 106.8(4) . . ?
C15 C14 C22 111.0(5) . . ?
N13 C14 H14 110.3 . . ?
C15 C14 H14 110.3 . . ?
C22 C14 H14 110.3 . . ?
N15 C15 C14 110.8(2) . . ?
N15 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
N15 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C16 N15 C15 121.2(2) . . ?
C16 N15 H15 112(2) . . ?
C15 N15 H15 118(2) . . ?
N15 C16 C17 122.8(2) . . ?
N15 C16 C21 118.7(2) . . ?
C17 C16 C21 118.5(2) . . ?
C16 C17 C18 120.0(3) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 121.2(3) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 119.1(3) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C21 C20 C19 120.5(3) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C16 120.7(3) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
C24 C22 C25 109.6(8) . . ?
C24 C22 C23 109.9(9) . . ?
C25 C22 C23 106.4(8) . . ?
C24 C22 C14 113.9(7) . . ?
C25 C22 C14 109.5(7) . . ?
C23 C22 C14 107.3(8) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C25B C22B C23B 108.9(8) . . ?
C25B C22B C24B 110.7(8) . . ?
C23B C22B C24B 109.9(9) . . ?
C25B C22B C14 109.9(7) . . ?
C23B C22B C14 110.0(8) . . ?
C24B C22B C14 107.6(6) . . ?
C22B C23B H23D 109.5 . . ?
C22B C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
C22B C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
C22B C24B H24D 109.5 . . ?
C22B C24B H24E 109.5 . . ?
H24D C24B H24E 109.5 . . ?
C22B C24B H24F 109.5 . . ?
H24D C24B H24F 109.5 . . ?
H24E C24B H24F 109.5 . . ?
C22B C25B H25D 109.5 . . ?
C22B C25B H25E 109.5 . . ?
H25D C25B H25E 109.5 . . ?
C22B C25B H25F 109.5 . . ?
H25D C25B H25F 109.5 . . ?
H25E C25B H25F 109.5 . . ?
O31 Si31 C31 106.63(11) . . ?
O31 Si31 C34 109.52(11) . . ?
C31 Si31 C34 116.05(12) . . ?
O31 Si31 C37 109.06(9) . . ?
C31 Si31 C37 105.06(12) . . ?
C34 Si31 C37 110.24(11) . . ?
C33 C31 C32 110.6(3) . . ?
C33 C31 Si31 114.7(2) . . ?
C32 C31 Si31 109.94(18) . . ?
C33 C31 H31 107.1 . . ?
C32 C31 H31 107.1 . . ?
Si31 C31 H31 107.1 . . ?
Si31 O31 H31A 109.5 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C35 C34 C36 109.0(2) . . ?
C35 C34 Si31 109.31(17) . . ?
C36 C34 Si31 111.34(19) . . ?
C35 C34 H34 109.1 . . ?
C36 C34 H34 109.1 . . ?
Si31 C34 H34 109.1 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C38 C37 C42 114.3(2) . . ?
C38 C37 Si31 119.55(18) . . ?
C42 C37 Si31 125.93(17) . . ?
F38 C38 C39 116.8(2) . . ?
F38 C38 C37 117.3(2) . . ?
C39 C38 C37 126.0(2) . . ?
C38 C39 C40 117.9(2) . . ?
C38 C39 H39 121.1 . . ?
C40 C39 H39 121.1 . . ?
C39 C40 C41 119.6(2) . . ?
C39 C40 H40 120.2 . . ?
C41 C40 H40 120.2 . . ?
C40 C41 C42 120.7(2) . . ?
C40 C41 H41 119.7 . . ?
C42 C41 H41 119.7 . . ?
C41 C42 C37 121.5(2) . . ?
C41 C42 C43 116.7(2) . . ?
C37 C42 C43 121.6(2) . . ?
O43 C43 N43 123.5(2) . . ?
O43 C43 C42 120.0(2) . . ?
N43 C43 C42 116.4(2) . . ?
C43 N43 C44 125.5(2) . . ?
C43 N43 H43 117.5(19) . . ?
C44 N43 H43 116.9(19) . . ?
N43 C44 C45 108.6(2) . . ?
N43 C44 C52 112.24(19) . . ?
C45 C44 C52 113.6(2) . . ?
N43 C44 H44 107.4 . . ?
C45 C44 H44 107.4 . . ?
C52 C44 H44 107.4 . . ?
N45 C45 C44 111.2(2) . . ?
N45 C45 H45A 109.4 . . ?
C44 C45 H45A 109.4 . . ?
N45 C45 H45B 109.4 . . ?
C44 C45 H45B 109.4 . . ?
H45A C45 H45B 108.0 . . ?
C46 N45 C45 121.0(2) . . ?
C46 N45 H45 115(2) . . ?
C45 N45 H45 114(2) . . ?
N45 C46 C47 122.6(2) . . ?
N45 C46 C51 118.9(2) . . ?
C47 C46 C51 118.5(2) . . ?
C48 C47 C46 119.7(3) . . ?
C48 C47 H47 120.2 . . ?
C46 C47 H47 120.2 . . ?
C49 C48 C47 121.6(3) . . ?
C49 C48 H48 119.2 . . ?
C47 C48 H48 119.2 . . ?
C50 C49 C48 118.9(3) . . ?
C50 C49 H49 120.5 . . ?
C48 C49 H49 120.5 . . ?
C49 C50 C51 120.8(3) . . ?
C49 C50 H50 119.6 . . ?
C51 C50 H50 119.6 . . ?
C50 C51 C46 120.5(3) . . ?
C50 C51 H51 119.8 . . ?
C46 C51 H51 119.8 . . ?
C55 C52 C53 109.3(2) . . ?
C55 C52 C54 110.3(2) . . ?
C53 C52 C54 108.2(2) . . ?
C55 C52 C44 111.7(2) . . ?
C53 C52 C44 108.5(2) . . ?
C54 C52 C44 108.8(2) . . ?
C52 C53 H53A 109.5 . . ?
C52 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C52 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C52 C54 H54A 109.5 . . ?
C52 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C52 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C52 C55 H55A 109.5 . . ?
C52 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
C52 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 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
O1 Si1 C1 C3 -168.7(2) . . . . ?
C4 Si1 C1 C3 -48.6(3) . . . . ?
C7 Si1 C1 C3 74.7(2) . . . . ?
O1 Si1 C1 C2 66.2(2) . . . . ?
C4 Si1 C1 C2 -173.77(19) . . . . ?
C7 Si1 C1 C2 -50.4(2) . . . . ?
O1 Si1 C4 C5 -69.1(2) . . . . ?
C1 Si1 C4 C5 173.68(19) . . . . ?
C7 Si1 C4 C5 51.1(2) . . . . ?
O1 Si1 C4 C6 54.5(3) . . . . ?
C1 Si1 C4 C6 -62.8(3) . . . . ?
C7 Si1 C4 C6 174.7(3) . . . . ?
C12 C7 C8 F8 -179.1(2) . . . . ?
Si1 C7 C8 F8 2.2(3) . . . . ?
C12 C7 C8 C9 0.7(4) . . . . ?
Si1 C7 C8 C9 -178.0(2) . . . . ?
F8 C8 C9 C10 179.2(3) . . . . ?
C7 C8 C9 C10 -0.6(5) . . . . ?
C8 C9 C10 C11 -0.2(5) . . . . ?
C9 C10 C11 C12 0.8(5) . . . . ?
C10 C11 C12 C7 -0.7(5) . . . . ?
C10 C11 C12 C13 176.8(3) . . . . ?
C8 C7 C12 C11 0.0(3) . . . . ?
Si1 C7 C12 C11 178.6(2) . . . . ?
C8 C7 C12 C13 -177.3(2) . . . . ?
Si1 C7 C12 C13 1.3(3) . . . . ?
C11 C12 C13 O13 -77.3(3) . . . . ?
C7 C12 C13 O13 100.1(3) . . . . ?
C11 C12 C13 N13 98.3(3) . . . . ?
C7 C12 C13 N13 -84.2(3) . . . . ?
O13 C13 N13 C14 -2.7(4) . . . . ?
C12 C13 N13 C14 -178.2(2) . . . . ?
C13 N13 C14 C15 -133.9(2) . . . . ?
C13 N13 C14 C22B 91.7(5) . . . . ?
C13 N13 C14 C22 106.6(5) . . . . ?
N13 C14 C15 N15 69.2(3) . . . . ?
C22B C14 C15 N15 -156.3(4) . . . . ?
C22 C14 C15 N15 -174.0(4) . . . . ?
C14 C15 N15 C16 -172.1(2) . . . . ?
C15 N15 C16 C17 -7.7(4) . . . . ?
C15 N15 C16 C21 173.6(2) . . . . ?
N15 C16 C17 C18 -178.5(3) . . . . ?
C21 C16 C17 C18 0.2(4) . . . . ?
C16 C17 C18 C19 0.5(5) . . . . ?
C17 C18 C19 C20 -0.4(5) . . . . ?
C18 C19 C20 C21 -0.4(5) . . . . ?
C19 C20 C21 C16 1.1(5) . . . . ?
N15 C16 C21 C20 177.8(3) . . . . ?
C17 C16 C21 C20 -1.0(4) . . . . ?
N13 C14 C22 C24 54.1(8) . . . . ?
C15 C14 C22 C24 -63.6(9) . . . . ?
N13 C14 C22 C25 177.2(6) . . . . ?
C15 C14 C22 C25 59.5(8) . . . . ?
N13 C14 C22 C23 -67.7(8) . . . . ?
C15 C14 C22 C23 174.6(7) . . . . ?
N13 C14 C22B C25B -161.7(5) . . . . ?
C15 C14 C22B C25B 67.8(7) . . . . ?
N13 C14 C22B C23B -41.8(9) . . . . ?
C15 C14 C22B C23B -172.3(8) . . . . ?
N13 C14 C22B C24B 77.8(8) . . . . ?
C15 C14 C22B C24B -52.7(8) . . . . ?
O31 Si31 C31 C33 -74.0(3) . . . . ?
C34 Si31 C31 C33 48.3(3) . . . . ?
C37 Si31 C31 C33 170.3(2) . . . . ?
O31 Si31 C31 C32 51.3(2) . . . . ?
C34 Si31 C31 C32 173.6(2) . . . . ?
C37 Si31 C31 C32 -64.4(2) . . . . ?
O31 Si31 C34 C35 -76.2(2) . . . . ?
C31 Si31 C34 C35 163.1(2) . . . . ?
C37 Si31 C34 C35 43.8(2) . . . . ?
O31 Si31 C34 C36 44.3(2) . . . . ?
C31 Si31 C34 C36 -76.5(2) . . . . ?
C37 Si31 C34 C36 164.3(2) . . . . ?
O31 Si31 C37 C38 -173.41(18) . . . . ?
C31 Si31 C37 C38 -59.4(2) . . . . ?
C34 Si31 C37 C38 66.3(2) . . . . ?
O31 Si31 C37 C42 0.7(2) . . . . ?
C31 Si31 C37 C42 114.7(2) . . . . ?
C34 Si31 C37 C42 -119.6(2) . . . . ?
C42 C37 C38 F38 177.0(2) . . . . ?
Si31 C37 C38 F38 -8.3(3) . . . . ?
C42 C37 C38 C39 -2.5(4) . . . . ?
Si31 C37 C38 C39 172.2(2) . . . . ?
F38 C38 C39 C40 -177.6(2) . . . . ?
C37 C38 C39 C40 1.8(4) . . . . ?
C38 C39 C40 C41 -0.3(4) . . . . ?
C39 C40 C41 C42 -0.4(4) . . . . ?
C40 C41 C42 C37 -0.4(4) . . . . ?
C40 C41 C42 C43 175.3(2) . . . . ?
C38 C37 C42 C41 1.7(3) . . . . ?
Si31 C37 C42 C41 -172.66(18) . . . . ?
C38 C37 C42 C43 -173.8(2) . . . . ?
Si31 C37 C42 C43 11.8(3) . . . . ?
C41 C42 C43 O43 -99.2(3) . . . . ?
C37 C42 C43 O43 76.5(3) . . . . ?
C41 C42 C43 N43 77.8(3) . . . . ?
C37 C42 C43 N43 -106.5(2) . . . . ?
O43 C43 N43 C44 -2.0(3) . . . . ?
C42 C43 N43 C44 -178.88(19) . . . . ?
C43 N43 C44 C45 -131.0(2) . . . . ?
C43 N43 C44 C52 102.5(3) . . . . ?
N43 C44 C45 N45 66.6(3) . . . . ?
C52 C44 C45 N45 -167.7(2) . . . . ?
C44 C45 N45 C46 -175.9(2) . . . . ?
C45 N45 C46 C47 -14.6(4) . . . . ?
C45 N45 C46 C51 167.4(3) . . . . ?
N45 C46 C47 C48 -178.4(3) . . . . ?
C51 C46 C47 C48 -0.4(5) . . . . ?
C46 C47 C48 C49 0.1(6) . . . . ?
C47 C48 C49 C50 -0.5(5) . . . . ?
C48 C49 C50 C51 1.2(5) . . . . ?
C49 C50 C51 C46 -1.5(4) . . . . ?
N45 C46 C51 C50 179.1(3) . . . . ?
C47 C46 C51 C50 1.1(4) . . . . ?
N43 C44 C52 C55 65.2(3) . . . . ?
C45 C44 C52 C55 -58.5(3) . . . . ?
N43 C44 C52 C53 -55.3(3) . . . . ?
C45 C44 C52 C53 -179.0(2) . . . . ?
N43 C44 C52 C54 -172.8(2) . . . . ?
C45 C44 C52 C54 63.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1A O43 0.84 1.89 2.680(2) 156.8 . yes
N45 H45 O31 0.86(3) 2.16(3) 3.007(3) 167(3) . yes
O31 H31A O13 0.84 1.91 2.675(2) 151.2 . yes
N15 H15 O1 0.78(3) 2.17(3) 2.947(3) 171(3) . yes

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_JF3112P1FMI
_database_code_depnum_ccdc_archive 'CCDC 2289939'
loop_
_audit_author_name
_audit_author_address
'James C. Fettinger'
;University of California, Davis
United States of America
;
_audit_update_record             
;
2023-08-21 deposited with the CCDC.	2025-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H24 F N O2 Si'
_chemical_formula_sum            'C24 H24 F N O2 Si'
_chemical_formula_weight         405.53

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'
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'
Si Si 0.0817 0.0704 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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'

_cell_length_a                   10.6067(19)
_cell_length_b                   10.8407(19)
_cell_length_c                   10.999(2)
_cell_angle_alpha                61.010(4)
_cell_angle_beta                 70.064(4)
_cell_angle_gamma                89.897(5)
_cell_volume                     1019.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9840
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      30.52

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.454
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.298
_exptl_absorpt_coefficient_mu    0.145
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9436
_exptl_absorpt_correction_T_max  0.9624
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Photon2 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            55770
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_av_R_equivalents  0.0151
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.084
_diffrn_reflns_theta_max         30.525
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             12230
_reflns_number_gt                12023
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.964
_reflns_Friedel_fraction_max     0.963
_reflns_Friedel_fraction_full    0.982

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

_computing_data_collection       'Apex3 (2019.11-0) (Bruker, 2019)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;

27 July, 2022 JF3112

A colorless block with approximate orthogonal dimensions 0.298 x 0.340
x 0.454mm3 was placed and optically centered on the Bruker(1) Venture
Dual Source Kappa Photon2 diffractometer at â\/E?173Â°C(100K). Indexing of
the unit cell used a random set of reflections collected from three
series of 0.5Â° wide omega-scans, 10 seconds per frame, and 30 frames
per series that were well distributed in reciprocal space. Data were
collected [MoKa] with 0.3Â° wide scans, variable time per frame
dependent upon detector 2theta angle and varying phi and omega angles
such that nearly all unique reflections were collected at least once.
The crystal to detector distance was 65.00mm, thus providing a
complete sphere of data to 2thetamax= 61.05Â°.
 Structural determination and Refinement:

All crystallographic calculations were performed on a Surface Pro7
with Intel i7-1065G7 at 1.30GHz with four cores, eight processors and
16GB of extended memory. Data collected were corrected for Lorentz and
polarization effects with Saint(1) and absorption using Blessingâ\/E?s
method and merged as incorporated with the program Sadabs(2,3). The
SHELXTL(4) program package was implemented to determine the probable
space group and set up the initial files. System symmetry, and lack of
systematic absences indicated the triclinic space groups P-1 (no.2) or
the non-centrosymmetric triclinic space group P1 (no. 1). Intensity
statistics were inconclusive with |E2-1|= 0.884 but leaning towards P-
1.  The structure was determined by direct methods with the non-
hydrogen atoms being located directly using the program XT(5) in both
P- 1 (Z=Zâ\/E?=1) and P1 (Zâ\/E?=2). The structures were refined with XL(6)
and it became apparent that in P-1 the molecule possessed multiple
forms of disorder, see Figure 1 below, while in P1 there were two
unique, nicely ordered molecules. The final refinement was performed
in P1 for the two unique molecules with all atoms refining freely,
including all of the hydrogen atoms. The only issue in P1 was the
location of the hydrogen atom labeled H(1) attached to O(1).  The atom
was freely located using HFIX 147 as was H(31) attached to O(31) but
this atom freely refined to about 0.7A from O(1) so it was therefore
refined with two distant restraints (DFIX), see Figure 2. The 55771
data collected were merged for least squares refinement to 12230
unique data [R(int)=0.0151]. All non-hydrogen atoms were refined
anisotropically. The final structure was refined to convergence with
R(F)=2.84%, wR(F2)=8.10%, GOF=1.020 for all 12230 unique reflections
[R(F)=2.80, wR(F2)=8.06% for those 12023 data with Fo > 4sigma(Fo)].
The final difference-Fourier map was featureless indicating that the
structure is both correct and complete.  An empirical correction for
extinction was also attempted and found to be negative and therefore
not applied. The absolute structure parameters were determined to be:
Flack(x)7, -0.0.030(15); Hooft(y)8, -0.035(12) and Parsons(z)6, -
0.017(11) indicating that the structureâ\/E?s absolute configuration has
been determined reliably; these values would be close to 1.0 if the
structure were inverted.

References:

1.	Bruker (2019) APEX3 (Version 2019.0) and (2016) SAINT (Version
8.37a). Bruker AXS Inc., Madison, Wisconsin, USA. 2.	An Empirical
Correction for Absorption Anisotropy, Blessing, R. H. (1995). Acta
Cryst., A51, 33-38.

3.	Sheldrick, G.M., SADABS (2016) Version 2016/2, â\/E?Siemens Area
Detector Absorption Correctionâ\/E? UniversitÃ?t GÃ?ttingen: GÃ?ttingen,
Germany.

4.	Sheldrick, G.M., (2002). SHELXTL. Version 6.1. Bruker AXS Inc.,
Madison, Wisconsin, USA.

5.	Sheldrick, G. M., (2014) SHELXT, UniversitÃ?t GÃ?ttingen: GÃ?ttingen,
Germany.  Structure determination program. Private communication.

6.	Sheldrick, G. M., (2017). SHELXL2017/1. UniversitÃ?t GÃ?ttingen:
GÃ?ttingen, Germany.

7.	On Enantiomorph-Polarity Estimation, Flack, H.D. (1983). Acta
Cryst., A39, 876-881.

8.	Hooft, R.W.W, Straver, L.H. & Spek, A.L. (2008). J. Appl, Cryst.
41, 96-103. Thompson,A.L. & Watkin, D.J. (2009). Tetrahedron

Acknowledgment:  We thank the National Science Foundation (Grant CHE-
1531193) for the Dual Source X-ray diffractometer.

James C. Fettinger, UC Davis, 27 July 2022
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0534P)²+0.2006P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 5770 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.030(15)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         12230
_refine_ls_number_parameters     715
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0810
_refine_ls_wR_factor_gt          0.0806
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.84893(4) 0.70526(4) 0.34588(4) 0.01250(9) Uani 1 1 d D . . . .
C1 C 0.79574(18) 0.50303(19) 0.42847(19) 0.0138(3) Uani 1 1 d . . . . .
O1 O 1.01384(14) 0.75788(15) 0.25363(15) 0.0176(3) Uani 1 1 d D . . . .
H1 H 1.0527(18) 0.697(4) 0.304(4) 0.11(2) Uiso 1 1 d D . . . .
C2 C 0.67623(19) 0.4524(2) 0.42762(19) 0.0147(3) Uani 1 1 d . . . . .
F2 F 0.59532(12) 0.54780(13) 0.37967(14) 0.0209(2) Uani 1 1 d . . . . .
C3 C 0.62749(19) 0.3123(2) 0.4735(2) 0.0167(3) Uani 1 1 d . . . . .
H3 H 0.536(3) 0.285(3) 0.471(3) 0.021(6) Uiso 1 1 d . . . . .
C4 C 0.7020(2) 0.2099(2) 0.5307(2) 0.0173(3) Uani 1 1 d . . . . .
H4 H 0.672(4) 0.109(4) 0.571(4) 0.034(8) Uiso 1 1 d . . . . .
C5 C 0.81912(19) 0.2502(2) 0.5435(2) 0.0164(3) Uani 1 1 d . . . . .
H5 H 0.874(3) 0.179(3) 0.580(3) 0.018(6) Uiso 1 1 d . . . . .
C6 C 0.86605(18) 0.39367(19) 0.4937(2) 0.0139(3) Uani 1 1 d . . . . .
C7 C 0.98911(18) 0.41862(19) 0.5213(2) 0.0146(3) Uani 1 1 d . . . . .
N7 N 1.07498(15) 0.53514(16) 0.45596(16) 0.0167(3) Uani 1 1 d . . . . .
O7 O 1.01008(16) 0.29923(16) 0.63085(18) 0.0218(3) Uani 1 1 d . . . . .
C8 C 1.1263(2) 0.3458(2) 0.6496(3) 0.0222(4) Uani 1 1 d . . . . .
H8A H 1.192(3) 0.285(3) 0.639(3) 0.027(6) Uiso 1 1 d . . . . .
H8B H 1.092(3) 0.333(3) 0.751(3) 0.033(7) Uiso 1 1 d . . . . .
C9 C 1.17854(16) 0.50512(17) 0.52318(18) 0.0162(3) Uani 1 1 d . . . . .
H9 H 1.262(3) 0.512(3) 0.450(3) 0.031(7) Uiso 1 1 d . . . . .
C10 C 1.19393(16) 0.60747(17) 0.57796(18) 0.0169(3) Uani 1 1 d . . . . .
H10 H 1.101(3) 0.596(3) 0.651(3) 0.017(5) Uiso 1 1 d . . . . .
C11 C 1.2406(3) 0.7635(3) 0.4476(3) 0.0287(5) Uani 1 1 d . . . . .
H11A H 1.334(4) 0.773(4) 0.371(4) 0.047(9) Uiso 1 1 d . . . . .
H11B H 1.249(4) 0.825(4) 0.486(4) 0.043(9) Uiso 1 1 d . . . . .
H11C H 1.168(4) 0.791(4) 0.396(4) 0.048(10) Uiso 1 1 d . . . . .
C12 C 1.2949(2) 0.5675(2) 0.6562(2) 0.0241(4) Uani 1 1 d . . . . .
H12A H 1.270(3) 0.462(3) 0.745(4) 0.038(7) Uiso 1 1 d . . . . .
H12B H 1.304(3) 0.634(3) 0.689(3) 0.035(8) Uiso 1 1 d . . . . .
H12C H 1.392(3) 0.579(4) 0.586(4) 0.036(7) Uiso 1 1 d . . . . .
C13 C 0.78867(18) 0.73826(19) 0.50648(19) 0.0139(3) Uani 1 1 d . . . . .
C14 C 0.8728(2) 0.8393(2) 0.5047(2) 0.0187(3) Uani 1 1 d . . . . .
H14 H 0.962(4) 0.890(4) 0.420(4) 0.036(9) Uiso 1 1 d . . . . .
C15 C 0.8334(2) 0.8676(2) 0.6221(2) 0.0218(4) Uani 1 1 d . . . . .
H15 H 0.907(4) 0.935(4) 0.625(4) 0.039(9) Uiso 1 1 d . . . . .
C16 C 0.7083(2) 0.7967(2) 0.7423(2) 0.0205(4) Uani 1 1 d . . . . .
H16 H 0.681(3) 0.799(3) 0.831(3) 0.030(8) Uiso 1 1 d . . . . .
C17 C 0.6224(2) 0.6972(2) 0.7455(2) 0.0184(3) Uani 1 1 d . . . . .
H17 H 0.530(3) 0.654(3) 0.826(3) 0.029(7) Uiso 1 1 d . . . . .
C18 C 0.66270(18) 0.6678(2) 0.6292(2) 0.0157(3) Uani 1 1 d . . . . .
H18 H 0.605(3) 0.597(3) 0.638(3) 0.020(6) Uiso 1 1 d . . . . .
C19 C 0.78245(18) 0.81980(19) 0.19827(19) 0.0139(3) Uani 1 1 d . . . . .
C20 C 0.8697(2) 0.8767(2) 0.0464(2) 0.0174(3) Uani 1 1 d . . . . .
H20 H 0.965(3) 0.838(3) 0.025(3) 0.028(7) Uiso 1 1 d . . . . .
C21 C 0.8322(2) 0.9719(2) -0.0698(2) 0.0222(4) Uani 1 1 d . . . . .
H21 H 0.901(4) 1.009(4) -0.180(4) 0.038(9) Uiso 1 1 d . . . . .
C22 C 0.7062(2) 1.0128(2) -0.0376(2) 0.0211(4) Uani 1 1 d . . . . .
H22 H 0.676(3) 1.077(3) -0.110(4) 0.026(7) Uiso 1 1 d . . . . .
C23 C 0.6173(2) 0.9570(2) 0.1121(2) 0.0182(3) Uani 1 1 d . . . . .
H23 H 0.536(3) 0.988(3) 0.134(3) 0.018(6) Uiso 1 1 d . . . . .
C24 C 0.65533(19) 0.8617(2) 0.2284(2) 0.0158(3) Uani 1 1 d . . . . .
H24 H 0.597(3) 0.826(3) 0.319(3) 0.019(6) Uiso 1 1 d . . . . .
Si31 Si 0.25000(4) 0.25000(4) 0.25000(4) 0.01203(9) Uani 1 1 d . . . . .
C31 C 0.30617(18) 0.45100(19) 0.16718(18) 0.0125(3) Uani 1 1 d . . . . .
O31 O 0.08424(13) 0.19834(15) 0.34474(15) 0.0166(2) Uani 1 1 d . . . . .
H31 H 0.048(3) 0.253(3) 0.288(3) 0.022(6) Uiso 1 1 d . . . . .
F32 F 0.50112(12) 0.40610(13) 0.22730(14) 0.0210(2) Uani 1 1 d . . . . .
C32 C 0.42278(18) 0.5014(2) 0.1745(2) 0.0146(3) Uani 1 1 d . . . . .
C33 C 0.46968(19) 0.6429(2) 0.1290(2) 0.0163(3) Uani 1 1 d . . . . .
H33 H 0.546(3) 0.666(3) 0.143(3) 0.025(7) Uiso 1 1 d . . . . .
C34 C 0.3948(2) 0.7444(2) 0.0703(2) 0.0168(3) Uani 1 1 d . . . . .
H34 H 0.426(3) 0.843(3) 0.041(3) 0.020(7) Uiso 1 1 d . . . . .
C35 C 0.28069(19) 0.7041(2) 0.0535(2) 0.0155(3) Uani 1 1 d . . . . .
H35 H 0.232(3) 0.774(4) 0.005(4) 0.031(8) Uiso 1 1 d . . . . .
C36 C 0.23732(17) 0.56144(19) 0.09809(19) 0.0132(3) Uani 1 1 d . . . . .
C37 C 0.12366(18) 0.53378(19) 0.0602(2) 0.0142(3) Uani 1 1 d . . . . .
N37 N 0.05989(15) 0.41261(15) 0.09881(16) 0.0154(2) Uani 1 1 d . . . . .
O37 O 0.09251(15) 0.65421(16) -0.03781(17) 0.0208(3) Uani 1 1 d . . . . .
C38 C -0.0262(2) 0.6018(2) -0.0506(3) 0.0206(4) Uani 1 1 d . . . . .
H38A H -0.016(3) 0.661(3) -0.152(3) 0.026(6) Uiso 1 1 d . . . . .
H38B H -0.114(3) 0.611(3) 0.024(3) 0.030(7) Uiso 1 1 d . . . . .
C39 C -0.02259(16) 0.44299(17) 0.00623(18) 0.0150(2) Uani 1 1 d . . . . .
H39 H 0.028(2) 0.434(3) -0.079(3) 0.015(5) Uiso 1 1 d . . . . .
C40 C -0.16169(17) 0.34308(18) 0.08810(19) 0.0190(3) Uani 1 1 d . . . . .
H40 H -0.215(3) 0.365(3) 0.165(3) 0.021(6) Uiso 1 1 d . . . . .
C41 C -0.2301(2) 0.3806(3) -0.0242(3) 0.0283(4) Uani 1 1 d . . . . .
H41A H -0.248(3) 0.483(3) -0.064(3) 0.030(6) Uiso 1 1 d . . . . .
H41B H -0.322(4) 0.310(4) 0.019(4) 0.059(11) Uiso 1 1 d . . . . .
H41C H -0.170(4) 0.370(4) -0.110(4) 0.053(10) Uiso 1 1 d . . . . .
C42 C -0.1480(2) 0.1860(3) 0.1566(3) 0.0269(4) Uani 1 1 d . . . . .
H42A H -0.237(3) 0.122(3) 0.202(3) 0.036(7) Uiso 1 1 d . . . . .
H42B H -0.106(3) 0.160(3) 0.229(3) 0.032(8) Uiso 1 1 d . . . . .
H42C H -0.091(3) 0.165(3) 0.084(4) 0.036(7) Uiso 1 1 d . . . . .
C43 C 0.30719(17) 0.21515(19) 0.09095(19) 0.0132(3) Uani 1 1 d . . . . .
C44 C 0.2238(2) 0.1099(2) 0.0971(2) 0.0183(3) Uani 1 1 d . . . . .
H44 H 0.141(3) 0.062(3) 0.178(4) 0.025(7) Uiso 1 1 d . . . . .
C45 C 0.2611(2) 0.0814(2) -0.0192(2) 0.0218(4) Uani 1 1 d . . . . .
H45 H 0.204(3) 0.012(3) -0.009(3) 0.027(7) Uiso 1 1 d . . . . .
C46 C 0.3840(2) 0.1557(2) -0.1438(2) 0.0204(4) Uani 1 1 d . . . . .
H46 H 0.413(3) 0.126(3) -0.221(3) 0.026(7) Uiso 1 1 d . . . . .
C47 C 0.4686(2) 0.2602(2) -0.1521(2) 0.0181(3) Uani 1 1 d . . . . .
H47 H 0.547(3) 0.313(3) -0.236(3) 0.021(6) Uiso 1 1 d . . . . .
C48 C 0.42933(18) 0.2902(2) -0.0362(2) 0.0155(3) Uani 1 1 d . . . . .
H48 H 0.489(3) 0.368(3) -0.046(3) 0.020(6) Uiso 1 1 d . . . . .
C49 C 0.31372(18) 0.13437(19) 0.39988(19) 0.0139(3) Uani 1 1 d . . . . .
C50 C 0.44085(19) 0.0927(2) 0.3713(2) 0.0155(3) Uani 1 1 d . . . . .
H50 H 0.504(3) 0.125(3) 0.263(3) 0.022(7) Uiso 1 1 d . . . . .
C51 C 0.4781(2) -0.0022(2) 0.4886(2) 0.0176(3) Uani 1 1 d . . . . .
H51 H 0.575(4) -0.028(4) 0.467(4) 0.036(8) Uiso 1 1 d . . . . .
C52 C 0.3888(2) -0.0572(2) 0.6373(2) 0.0194(3) Uani 1 1 d . . . . .
H52 H 0.409(3) -0.128(3) 0.725(4) 0.028(7) Uiso 1 1 d . . . . .
C53 C 0.2622(2) -0.0179(2) 0.6691(2) 0.0198(3) Uani 1 1 d . . . . .
H53 H 0.204(3) -0.055(3) 0.769(3) 0.018(6) Uiso 1 1 d . . . . .
C54 C 0.22488(19) 0.0768(2) 0.5507(2) 0.0170(3) Uani 1 1 d . . . . .
H54 H 0.137(3) 0.093(3) 0.579(3) 0.016(6) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si1 O1 1.6268(14) . ?
Si1 C13 1.8704(18) . ?
Si1 C19 1.8705(19) . ?
Si1 C1 1.9169(19) . ?
C1 C2 1.387(3) . ?
C1 C6 1.419(3) . ?
O1 H1 0.842(14) . ?
C2 F2 1.364(2) . ?
C2 C3 1.383(3) . ?
C3 C4 1.383(3) . ?
C3 H3 1.03(3) . ?
C4 C5 1.391(3) . ?
C4 H4 0.97(3) . ?
C5 C6 1.400(3) . ?
C5 H5 0.97(3) . ?
C6 C7 1.490(2) . ?
C7 N7 1.273(2) . ?
C7 O7 1.359(2) . ?
N7 C9 1.476(2) . ?
O7 C8 1.447(3) . ?
C8 C9 1.541(3) . ?
C8 H8A 0.97(3) . ?
C8 H8B 0.99(3) . ?
C9 C10 1.529(2) . ?
C9 H9 0.94(3) . ?
C10 C11 1.526(3) . ?
C10 C12 1.530(3) . ?
C10 H10 1.00(2) . ?
C11 H11A 1.02(4) . ?
C11 H11B 0.97(3) . ?
C11 H11C 1.06(4) . ?
C12 H12A 1.04(3) . ?
C12 H12B 0.96(3) . ?
C12 H12C 1.02(3) . ?
C13 C18 1.402(2) . ?
C13 C14 1.402(2) . ?
C14 C15 1.398(3) . ?
C14 H14 0.98(4) . ?
C15 C16 1.386(3) . ?
C15 H15 1.09(4) . ?
C16 C17 1.392(3) . ?
C16 H16 0.93(3) . ?
C17 C18 1.394(3) . ?
C17 H17 0.99(3) . ?
C18 H18 0.93(3) . ?
C19 C24 1.405(2) . ?
C19 C20 1.406(2) . ?
C20 C21 1.387(3) . ?
C20 H20 1.08(3) . ?
C21 C22 1.392(3) . ?
C21 H21 1.04(3) . ?
C22 C23 1.394(3) . ?
C22 H22 0.93(3) . ?
C23 C24 1.392(3) . ?
C23 H23 0.92(3) . ?
C24 H24 0.85(3) . ?
Si31 O31 1.6369(14) . ?
Si31 C43 1.8674(17) . ?
Si31 C49 1.8707(19) . ?
Si31 C31 1.9088(18) . ?
C31 C32 1.396(2) . ?
C31 C36 1.427(2) . ?
O31 H31 0.84(3) . ?
F32 C32 1.356(2) . ?
C32 C33 1.393(3) . ?
C33 C34 1.384(3) . ?
C33 H33 0.92(3) . ?
C34 C35 1.386(3) . ?
C34 H34 0.98(3) . ?
C35 C36 1.399(2) . ?
C35 H35 0.96(4) . ?
C36 C37 1.477(2) . ?
C37 N37 1.277(2) . ?
C37 O37 1.361(2) . ?
N37 C39 1.481(2) . ?
O37 C38 1.459(3) . ?
C38 C39 1.526(3) . ?
C38 H38A 0.94(3) . ?
C38 H38B 1.05(3) . ?
C39 C40 1.522(2) . ?
C39 H39 0.96(2) . ?
C40 C42 1.523(3) . ?
C40 C41 1.530(3) . ?
C40 H40 0.99(3) . ?
C41 H41A 1.02(3) . ?
C41 H41B 1.04(4) . ?
C41 H41C 1.00(4) . ?
C42 H42A 0.98(3) . ?
C42 H42B 0.97(3) . ?
C42 H42C 0.95(3) . ?
C43 C48 1.400(2) . ?
C43 C44 1.406(2) . ?
C44 C45 1.388(3) . ?
C44 H44 0.92(3) . ?
C45 C46 1.394(3) . ?
C45 H45 0.91(3) . ?
C46 C47 1.394(3) . ?
C46 H46 1.00(3) . ?
C47 C48 1.395(3) . ?
C47 H47 0.92(3) . ?
C48 H48 1.00(3) . ?
C49 C54 1.401(2) . ?
C49 C50 1.403(2) . ?
C50 C51 1.392(3) . ?
C50 H50 1.02(3) . ?
C51 C52 1.389(3) . ?
C51 H51 1.04(4) . ?
C52 C53 1.389(3) . ?
C52 H52 0.99(3) . ?
C53 C54 1.400(3) . ?
C53 H53 0.92(3) . ?
C54 H54 0.93(3) . ?

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 C13 111.58(8) . . ?
O1 Si1 C19 102.49(8) . . ?
C13 Si1 C19 111.19(8) . . ?
O1 Si1 C1 110.66(8) . . ?
C13 Si1 C1 107.43(8) . . ?
C19 Si1 C1 113.54(8) . . ?
C2 C1 C6 113.91(16) . . ?
C2 C1 Si1 119.10(14) . . ?
C6 C1 Si1 126.99(14) . . ?
Si1 O1 H1 109.0(15) . . ?
F2 C2 C3 115.28(16) . . ?
F2 C2 C1 118.06(16) . . ?
C3 C2 C1 126.64(18) . . ?
C4 C3 C2 117.54(17) . . ?
C4 C3 H3 121.9(16) . . ?
C2 C3 H3 120.4(16) . . ?
C3 C4 C5 119.50(17) . . ?
C3 C4 H4 123(2) . . ?
C5 C4 H4 117(2) . . ?
C4 C5 C6 121.12(18) . . ?
C4 C5 H5 120.0(17) . . ?
C6 C5 H5 118.7(17) . . ?
C5 C6 C1 121.12(17) . . ?
C5 C6 C7 114.75(16) . . ?
C1 C6 C7 124.07(16) . . ?
N7 C7 O7 117.25(17) . . ?
N7 C7 C6 128.56(16) . . ?
O7 C7 C6 114.19(16) . . ?
C7 N7 C9 108.19(14) . . ?
C7 O7 C8 106.38(15) . . ?
O7 C8 C9 104.52(15) . . ?
O7 C8 H8A 106.5(16) . . ?
C9 C8 H8A 113.2(17) . . ?
O7 C8 H8B 106.9(18) . . ?
C9 C8 H8B 112.3(18) . . ?
H8A C8 H8B 113(2) . . ?
N7 C9 C10 111.73(12) . . ?
N7 C9 C8 103.26(14) . . ?
C10 C9 C8 114.16(14) . . ?
N7 C9 H9 108.2(17) . . ?
C10 C9 H9 111.0(18) . . ?
C8 C9 H9 108.0(18) . . ?
C11 C10 C9 111.08(15) . . ?
C11 C10 C12 110.19(16) . . ?
C9 C10 C12 110.49(14) . . ?
C11 C10 H10 108.6(14) . . ?
C9 C10 H10 106.1(14) . . ?
C12 C10 H10 110.3(14) . . ?
C10 C11 H11A 108(2) . . ?
C10 C11 H11B 109(2) . . ?
H11A C11 H11B 109(3) . . ?
C10 C11 H11C 110(2) . . ?
H11A C11 H11C 110(3) . . ?
H11B C11 H11C 111(3) . . ?
C10 C12 H12A 114.6(18) . . ?
C10 C12 H12B 108.9(18) . . ?
H12A C12 H12B 111(3) . . ?
C10 C12 H12C 113.0(18) . . ?
H12A C12 H12C 105(2) . . ?
H12B C12 H12C 104(3) . . ?
C18 C13 C14 117.77(16) . . ?
C18 C13 Si1 123.47(14) . . ?
C14 C13 Si1 118.76(13) . . ?
C15 C14 C13 121.26(18) . . ?
C15 C14 H14 119(2) . . ?
C13 C14 H14 120(2) . . ?
C16 C15 C14 119.96(18) . . ?
C16 C15 H15 120.6(18) . . ?
C14 C15 H15 118.9(18) . . ?
C15 C16 C17 119.75(17) . . ?
C15 C16 H16 125(2) . . ?
C17 C16 H16 114.7(19) . . ?
C16 C17 C18 120.16(17) . . ?
C16 C17 H17 119.5(18) . . ?
C18 C17 H17 120.2(18) . . ?
C17 C18 C13 121.10(18) . . ?
C17 C18 H18 117.6(18) . . ?
C13 C18 H18 121.2(17) . . ?
C24 C19 C20 117.72(17) . . ?
C24 C19 Si1 124.32(13) . . ?
C20 C19 Si1 117.78(14) . . ?
C21 C20 C19 121.23(18) . . ?
C21 C20 H20 122.0(16) . . ?
C19 C20 H20 116.7(16) . . ?
C20 C21 C22 120.18(18) . . ?
C20 C21 H21 118(2) . . ?
C22 C21 H21 122(2) . . ?
C21 C22 C23 119.74(19) . . ?
C21 C22 H22 124.2(19) . . ?
C23 C22 H22 116.0(19) . . ?
C24 C23 C22 119.91(18) . . ?
C24 C23 H23 119.7(18) . . ?
C22 C23 H23 120.3(18) . . ?
C23 C24 C19 121.22(17) . . ?
C23 C24 H24 117(2) . . ?
C19 C24 H24 121(2) . . ?
O31 Si31 C43 111.68(8) . . ?
O31 Si31 C49 101.18(8) . . ?
C43 Si31 C49 111.92(8) . . ?
O31 Si31 C31 110.98(7) . . ?
C43 Si31 C31 107.82(7) . . ?
C49 Si31 C31 113.25(8) . . ?
C32 C31 C36 113.78(16) . . ?
C32 C31 Si31 120.09(14) . . ?
C36 C31 Si31 126.11(13) . . ?
Si31 O31 H31 107.2(18) . . ?
F32 C32 C33 115.79(16) . . ?
F32 C32 C31 118.03(16) . . ?
C33 C32 C31 126.17(17) . . ?
C34 C33 C32 117.60(17) . . ?
C34 C33 H33 122.2(19) . . ?
C32 C33 H33 120.2(19) . . ?
C33 C34 C35 119.79(17) . . ?
C33 C34 H34 117.8(18) . . ?
C35 C34 H34 122.4(18) . . ?
C34 C35 C36 121.25(18) . . ?
C34 C35 H35 122(2) . . ?
C36 C35 H35 117(2) . . ?
C35 C36 C31 121.26(16) . . ?
C35 C36 C37 116.50(16) . . ?
C31 C36 C37 122.10(15) . . ?
N37 C37 O37 117.21(16) . . ?
N37 C37 C36 127.98(16) . . ?
O37 C37 C36 114.58(15) . . ?
C37 N37 C39 106.99(14) . . ?
C37 O37 C38 104.87(15) . . ?
O37 C38 C39 103.55(15) . . ?
O37 C38 H38A 106.8(17) . . ?
C39 C38 H38A 117.2(17) . . ?
O37 C38 H38B 107.6(16) . . ?
C39 C38 H38B 109.4(16) . . ?
H38A C38 H38B 112(2) . . ?
N37 C39 C40 114.66(13) . . ?
N37 C39 C38 102.37(13) . . ?
C40 C39 C38 115.34(14) . . ?
N37 C39 H39 108.3(14) . . ?
C40 C39 H39 107.6(14) . . ?
C38 C39 H39 108.3(14) . . ?
C39 C40 C42 111.26(14) . . ?
C39 C40 C41 108.61(14) . . ?
C42 C40 C41 110.20(17) . . ?
C39 C40 H40 105.4(15) . . ?
C42 C40 H40 112.3(15) . . ?
C41 C40 H40 108.9(15) . . ?
C40 C41 H41A 111.0(16) . . ?
C40 C41 H41B 114(2) . . ?
H41A C41 H41B 109(3) . . ?
C40 C41 H41C 109(2) . . ?
H41A C41 H41C 110(3) . . ?
H41B C41 H41C 104(3) . . ?
C40 C42 H42A 111.0(18) . . ?
C40 C42 H42B 111.5(18) . . ?
H42A C42 H42B 111(3) . . ?
C40 C42 H42C 112.9(19) . . ?
H42A C42 H42C 105(3) . . ?
H42B C42 H42C 105(3) . . ?
C48 C43 C44 117.91(16) . . ?
C48 C43 Si31 123.11(14) . . ?
C44 C43 Si31 118.98(13) . . ?
C45 C44 C43 121.09(17) . . ?
C45 C44 H44 120(2) . . ?
C43 C44 H44 119(2) . . ?
C44 C45 C46 120.21(19) . . ?
C44 C45 H45 117.5(18) . . ?
C46 C45 H45 122.3(18) . . ?
C45 C46 C47 119.70(17) . . ?
C45 C46 H46 118.5(17) . . ?
C47 C46 H46 121.6(17) . . ?
C46 C47 C48 119.85(17) . . ?
C46 C47 H47 120.1(17) . . ?
C48 C47 H47 119.9(18) . . ?
C47 C48 C43 121.22(18) . . ?
C47 C48 H48 118.8(16) . . ?
C43 C48 H48 120.0(16) . . ?
C54 C49 C50 117.76(17) . . ?
C54 C49 Si31 117.95(13) . . ?
C50 C49 Si31 124.10(13) . . ?
C51 C50 C49 121.28(17) . . ?
C51 C50 H50 118.7(17) . . ?
C49 C50 H50 119.8(17) . . ?
C52 C51 C50 119.98(17) . . ?
C52 C51 H51 119(2) . . ?
C50 C51 H51 121(2) . . ?
C53 C52 C51 120.03(18) . . ?
C53 C52 H52 116.8(18) . . ?
C51 C52 H52 123.2(18) . . ?
C52 C53 C54 119.76(17) . . ?
C52 C53 H53 119.0(19) . . ?
C54 C53 H53 121.2(19) . . ?
C53 C54 C49 121.19(17) . . ?
C53 C54 H54 115.9(17) . . ?
C49 C54 H54 122.7(17) . . ?

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
C6 C1 C2 F2 174.16(15) . . . . ?
Si1 C1 C2 F2 -5.6(2) . . . . ?
C6 C1 C2 C3 -4.6(3) . . . . ?
Si1 C1 C2 C3 175.65(14) . . . . ?
F2 C2 C3 C4 -176.64(15) . . . . ?
C1 C2 C3 C4 2.1(3) . . . . ?
C2 C3 C4 C5 1.7(3) . . . . ?
C3 C4 C5 C6 -2.7(3) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4 C5 C6 C7 177.47(16) . . . . ?
C2 C1 C6 C5 3.3(2) . . . . ?
Si1 C1 C6 C5 -176.90(13) . . . . ?
C2 C1 C6 C7 -173.85(16) . . . . ?
Si1 C1 C6 C7 5.9(3) . . . . ?
C5 C6 C7 N7 159.12(18) . . . . ?
C1 C6 C7 N7 -23.5(3) . . . . ?
C5 C6 C7 O7 -20.6(2) . . . . ?
C1 C6 C7 O7 156.73(17) . . . . ?
O7 C7 N7 C9 -0.4(2) . . . . ?
C6 C7 N7 C9 179.83(16) . . . . ?
N7 C7 O7 C8 4.5(2) . . . . ?
C6 C7 O7 C8 -175.77(16) . . . . ?
C7 O7 C8 C9 -6.1(2) . . . . ?
C7 N7 C9 C10 -126.62(15) . . . . ?
C7 N7 C9 C8 -3.49(19) . . . . ?
O7 C8 C9 N7 5.80(19) . . . . ?
O7 C8 C9 C10 127.30(15) . . . . ?
N7 C9 C10 C11 -61.08(18) . . . . ?
C8 C9 C10 C11 -177.79(17) . . . . ?
N7 C9 C10 C12 176.31(15) . . . . ?
C8 C9 C10 C12 59.60(19) . . . . ?
O1 Si1 C13 C18 -160.50(15) . . . . ?
C19 Si1 C13 C18 85.75(17) . . . . ?
C1 Si1 C13 C18 -39.04(18) . . . . ?
O1 Si1 C13 C14 19.91(17) . . . . ?
C19 Si1 C13 C14 -93.84(16) . . . . ?
C1 Si1 C13 C14 141.37(15) . . . . ?
C18 C13 C14 C15 0.8(3) . . . . ?
Si1 C13 C14 C15 -179.58(17) . . . . ?
C13 C14 C15 C16 -0.9(3) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C16 C17 C18 C13 -0.8(3) . . . . ?
C14 C13 C18 C17 0.0(3) . . . . ?
Si1 C13 C18 C17 -179.55(15) . . . . ?
O1 Si1 C19 C24 -151.85(15) . . . . ?
C13 Si1 C19 C24 -32.52(18) . . . . ?
C1 Si1 C19 C24 88.76(16) . . . . ?
O1 Si1 C19 C20 23.09(16) . . . . ?
C13 Si1 C19 C20 142.42(14) . . . . ?
C1 Si1 C19 C20 -96.29(15) . . . . ?
C24 C19 C20 C21 0.6(3) . . . . ?
Si1 C19 C20 C21 -174.73(16) . . . . ?
C19 C20 C21 C22 -0.1(3) . . . . ?
C20 C21 C22 C23 -0.4(3) . . . . ?
C21 C22 C23 C24 0.5(3) . . . . ?
C22 C23 C24 C19 0.0(3) . . . . ?
C20 C19 C24 C23 -0.5(3) . . . . ?
Si1 C19 C24 C23 174.48(14) . . . . ?
C36 C31 C32 F32 -174.84(15) . . . . ?
Si31 C31 C32 F32 6.6(2) . . . . ?
C36 C31 C32 C33 3.5(2) . . . . ?
Si31 C31 C32 C33 -174.99(14) . . . . ?
F32 C32 C33 C34 178.17(16) . . . . ?
C31 C32 C33 C34 -0.2(3) . . . . ?
C32 C33 C34 C35 -2.4(3) . . . . ?
C33 C34 C35 C36 1.5(3) . . . . ?
C34 C35 C36 C31 2.1(3) . . . . ?
C34 C35 C36 C37 -173.74(16) . . . . ?
C32 C31 C36 C35 -4.3(2) . . . . ?
Si31 C31 C36 C35 174.07(13) . . . . ?
C32 C31 C36 C37 171.23(15) . . . . ?
Si31 C31 C36 C37 -10.4(2) . . . . ?
C35 C36 C37 N37 -174.04(16) . . . . ?
C31 C36 C37 N37 10.2(3) . . . . ?
C35 C36 C37 O37 11.7(2) . . . . ?
C31 C36 C37 O37 -164.07(16) . . . . ?
O37 C37 N37 C39 6.4(2) . . . . ?
C36 C37 N37 C39 -167.76(16) . . . . ?
N37 C37 O37 C38 8.6(2) . . . . ?
C36 C37 O37 C38 -176.47(15) . . . . ?
C37 O37 C38 C39 -18.85(19) . . . . ?
C37 N37 C39 C40 -143.30(14) . . . . ?
C37 N37 C39 C38 -17.65(18) . . . . ?
O37 C38 C39 N37 21.91(18) . . . . ?
O37 C38 C39 C40 147.11(14) . . . . ?
N37 C39 C40 C42 -54.57(19) . . . . ?
C38 C39 C40 C42 -173.14(18) . . . . ?
N37 C39 C40 C41 -176.04(16) . . . . ?
C38 C39 C40 C41 65.4(2) . . . . ?
O31 Si31 C43 C48 157.03(14) . . . . ?
C49 Si31 C43 C48 -90.33(16) . . . . ?
C31 Si31 C43 C48 34.86(17) . . . . ?
O31 Si31 C43 C44 -22.25(17) . . . . ?
C49 Si31 C43 C44 90.38(16) . . . . ?
C31 Si31 C43 C44 -144.43(15) . . . . ?
C48 C43 C44 C45 -0.1(3) . . . . ?
Si31 C43 C44 C45 179.20(17) . . . . ?
C43 C44 C45 C46 1.1(3) . . . . ?
C44 C45 C46 C47 -0.9(3) . . . . ?
C45 C46 C47 C48 -0.3(3) . . . . ?
C46 C47 C48 C43 1.3(3) . . . . ?
C44 C43 C48 C47 -1.1(3) . . . . ?
Si31 C43 C48 C47 179.64(15) . . . . ?
O31 Si31 C49 C54 -21.29(16) . . . . ?
C43 Si31 C49 C54 -140.33(14) . . . . ?
C31 Si31 C49 C54 97.54(15) . . . . ?
O31 Si31 C49 C50 153.63(15) . . . . ?
C43 Si31 C49 C50 34.59(18) . . . . ?
C31 Si31 C49 C50 -87.54(16) . . . . ?
C54 C49 C50 C51 -0.3(3) . . . . ?
Si31 C49 C50 C51 -175.19(14) . . . . ?
C49 C50 C51 C52 -0.2(3) . . . . ?
C50 C51 C52 C53 0.3(3) . . . . ?
C51 C52 C53 C54 0.1(3) . . . . ?
C52 C53 C54 C49 -0.6(3) . . . . ?
C50 C49 C54 C53 0.7(3) . . . . ?
Si31 C49 C54 C53 175.92(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3 H3 F32 1.03(3) 2.51(3) 3.157(2) 120.0(19) . yes
O31 H31 N37 0.84(3) 1.91(3) 2.676(2) 151(3) . yes
C33 H33 F2 0.92(3) 2.53(3) 3.192(2) 129(2) . yes
O1 H1 N7 0.842(14) 1.834(19) 2.641(2) 160(2) . yes

_refine_diff_density_max         0.417
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_JF3155FF
_database_code_depnum_ccdc_archive 'CCDC 2311643'
loop_
_audit_author_name
_audit_author_address
'James C. Fettinger'
;University of California, Davis
United States of America
;
_audit_update_record             
;
2023-12-02 deposited with the CCDC.	2025-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H12 B F24, C48 H72 F2 N4 Na O5 Si2'
_chemical_formula_sum            'C80 H84 B F26 N4 Na O5 Si2'
_chemical_formula_weight         1765.49

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'
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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'

_cell_length_a                   12.8653(14)
_cell_length_b                   12.9386(14)
_cell_length_c                   14.2525(16)
_cell_angle_alpha                76.0784(15)
_cell_angle_beta                 80.3071(16)
_cell_angle_gamma                65.8644(15)
_cell_volume                     2094.9(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.45

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_F_000             910
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.459
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.157
_shelx_estimated_absorpt_T_min   0.923
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8636
_exptl_absorpt_correction_T_max  0.9541
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Photon2 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33064
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.740
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             19110
_reflns_number_gt                16393
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.987
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_fraction_full    0.992

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

_computing_data_collection       'Apex3 (2019.11-0) (Bruker, 2019)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    
'SHELXT (Sheldrick, 2015) Acta Cryst., A71, 3-8'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;

29 November, 2023 JF3155  YPC-3-170

A colorless plate with approximate orthogonal dimensions 0.190 x 0.459
x 0.288mm3 was placed and optically centered on the Bruker(1) Duo
APEXII CCD system at â\/E?183Â°C(90K).  Indexing of the unit cell used a
random set of reflections collected from three series of 0.5Â° wide
omega-scans, 10 seconds per frame, and 30 frames per series that were
well distributed in reciprocal space. Five omega-scan data frame
series were collected [MoKa] with 0.3Â° wide scans, 30 seconds per
frame and 606 frames collected per series at varying phi angles. The
crystal to detector distance was 5.15cm, thus providing a complete
sphere of data to 2ThetaMax=55.18Â°.

Structural determination and Refinement:

All crystallographic calculations were performed on a Surface Pro7
with Intel i7-1065G7 at 1.30GHz with four cores, eight processors and
16GB of extended memory. Data collected were corrected for Lorentz and
polarization effects with Saint(1) and absorption using Blessingâ\/E?s
method and merged as incorporated with the program Sadabs(2,3). The
SHELXTL(4) program package was implemented to determine the probable
space group and set up the initial files. System symmetry, lack of
systematic absences and intensity statistics indicated the non-
centrosymmetric triclinic space group P1 (no.1). The structure was
determined by direct methods with the location of a majority of the
non-hydrogen atoms for the two molecules with the program XT(5). The
structure was refined with XL(6). The 33064 data collected were merged
for least squares refinement to 19110 unique data [R(int)=0.0161]. All
full occupancy non-hydrogen atoms were refined anisotropically.
Multiple disorders were observed and optimized for the two molecules.
Hydrogen atoms attached to Nitrogen atoms labeled N13, N18, N37 and
N42 had distance (DFIX) restraints applied while the thermal
parameters were allowed to refine freely. One of the moieties attached
to the central Na1 atoms was found to be disordered and along with two
water molecules bound to the central Na1 atom that was optimized to
0.82:0.18. The B(C8H3F6)4 molecule was found to possess multiple
disorders that were also optimized. A variety of restraints were
required for structural refinement and those commands included
distance restraints (SADI, DFIX), similar thermal motion restraints
for atoms that were overlapping or nearly so (SIMU, ISOR, EADP) and
fragments deemed to be identical were optimized (SAME). Hydrogen atoms
were otherwise idealized throughout the final refinement. The final
structure was refined to convergence with R(F)=7.02%, wR(F2)=16.49%,
GOF=1.033 for all 19110 unique reflections [R(F)=5.96%, wR(F2)=15.49%
for those 16393 data with Fo > 4sigma(Fo)]. The final difference-
Fourier map was featureless indicating that the structure is both
correct and complete.


References:

1.	Bruker (2019) APEX3 (Version 2019.1) and (2016) SAINT (Version
8.37a). Bruker AXS Inc., Madison, Wisconsin, USA. 2.	An Empirical
Correction for Absorption Anisotropy, Blessing, R. H. (1995). Acta
Cryst., A51, 33-38.

3.	Sheldrick, G.M., SADABS (2016) Version 2016/2, â\/E?Siemens Area
Detector Absorption Correctionâ\/E? UniversitÃ?t GÃ?ttingen: GÃ?ttingen,
Germany.

4.	Sheldrick, G.M., (2002). SHELXTL. Version 6.1. Bruker AXS Inc.,
Madison, Wisconsin, USA.

5.	Sheldrick, G. M., (2014) SHELXT, UniversitÃ?t GÃ?ttingen: GÃ?ttingen,
Germany.  Structure determination program. Private communication.

6.	Sheldrick, G. M., (2019). SHELXL2019/3. UniversitÃ?t GÃ?ttingen:
GÃ?ttingen, Germany.


Acknowledgment:  We thank the National Science Foundation (Grant CHE-
0840444) for the Dual Source X-ray diffractometer.

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0929P)²+1.2707P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 7001 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.01(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         19110
_refine_ls_number_parameters     1442
_refine_ls_number_restraints     455
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1649
_refine_ls_wR_factor_gt          0.1549
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Na1 Na 0.3014(5) 0.7666(6) 0.2776(6) 0.0422(13) Uani 0.82 1 d D U P A 1
Si1 Si 0.15422(13) 0.52011(14) 0.49985(11) 0.0344(3) Uani 0.82 1 d D U P A 1
C1 C 0.2399(5) 0.4935(6) 0.6054(4) 0.0469(15) Uani 0.82 1 d D U P A 1
H1 H 0.245905 0.417096 0.646541 0.056 Uiso 0.82 1 calc R U P A 1
O1 O 0.1309(4) 0.6544(4) 0.4459(3) 0.0367(9) Uani 0.82 1 d D . P A 1
H1A H 0.091(8) 0.683(9) 0.398(5) 0.08(3) Uiso 0.82 1 d D . P B 1
C2 C 0.3611(6) 0.4868(8) 0.5706(6) 0.062(2) Uani 0.82 1 d D . P A 1
H2A H 0.357874 0.561199 0.531129 0.092 Uiso 0.82 1 calc R U P A 1
H2B H 0.398629 0.426467 0.531691 0.092 Uiso 0.82 1 calc R U P A 1
H2C H 0.404505 0.468389 0.626843 0.092 Uiso 0.82 1 calc R U P A 1
C3 C 0.1823(7) 0.5842(7) 0.6688(5) 0.059(2) Uani 0.82 1 d D U P A 1
H3A H 0.226768 0.563867 0.724698 0.088 Uiso 0.82 1 calc R U P A 1
H3B H 0.104962 0.587614 0.691442 0.088 Uiso 0.82 1 calc R U P A 1
H3C H 0.178290 0.659689 0.630995 0.088 Uiso 0.82 1 calc R U P A 1
C4 C 0.0232(6) 0.4851(6) 0.5386(5) 0.0461(15) Uani 0.82 1 d D U P A 1
H4 H 0.049418 0.407200 0.581630 0.055 Uiso 0.82 1 calc R U P A 1
C5 C -0.0277(6) 0.4731(7) 0.4545(6) 0.0557(18) Uani 0.82 1 d D U P A 1
H5A H -0.088970 0.444893 0.479896 0.084 Uiso 0.82 1 calc R U P A 1
H5B H 0.031913 0.418312 0.418034 0.084 Uiso 0.82 1 calc R U P A 1
H5C H -0.058886 0.548435 0.411639 0.084 Uiso 0.82 1 calc R U P A 1
C6 C -0.0679(7) 0.5656(8) 0.5995(8) 0.072(2) Uani 0.82 1 d D U P A 1
H6A H -0.091205 0.645143 0.563070 0.107 Uiso 0.82 1 calc R U P A 1
H6B H -0.037067 0.559994 0.659702 0.107 Uiso 0.82 1 calc R U P A 1
H6C H -0.134195 0.543776 0.614890 0.107 Uiso 0.82 1 calc R U P A 1
C7 C 0.2545(3) 0.4198(3) 0.4121(3) 0.0324(11) Uani 0.82 1 d DG . P A 1
C8 C 0.3117(3) 0.3073(3) 0.4592(2) 0.0401(13) Uani 0.82 1 d DG . P A 1
C9 C 0.4090(3) 0.2344(3) 0.4137(3) 0.0400(14) Uani 0.82 1 d G . P A 1
H9 H 0.448069 0.157466 0.445848 0.048 Uiso 0.82 1 calc R U P A 1
C10 C 0.4490(3) 0.2741(3) 0.3211(3) 0.0405(12) Uani 0.82 1 d G . P A 1
H10 H 0.515482 0.224244 0.289955 0.049 Uiso 0.82 1 calc R U P A 1
C11 C 0.3918(4) 0.3866(4) 0.2740(2) 0.0340(14) Uani 0.82 1 d G . P A 1
H11 H 0.419157 0.413709 0.210706 0.041 Uiso 0.82 1 calc R U P A 1
C12 C 0.2945(4) 0.4595(3) 0.3195(3) 0.0318(9) Uani 0.82 1 d DG . P A 1
F8 F 0.2755(4) 0.2683(3) 0.5460(3) 0.0570(11) Uani 0.82 1 d D U P A 1
O3 O 0.2353(5) 0.8042(5) 0.4267(4) 0.0540(12) Uani 0.82 1 d D U P A 1
H3D H 0.214(8) 0.867(3) 0.445(3) 0.081 Uiso 0.82 1 d D U P C 1
H3E H 0.210(8) 0.761(5) 0.470(3) 0.081 Uiso 0.82 1 d D U P D 1
Na1B Na 0.276(3) 0.785(3) 0.277(3) 0.041(2) Uani 0.18 1 d D U P A 2
Si1B Si 0.2036(8) 0.5807(7) 0.4861(6) 0.0510(18) Uani 0.18 1 d D U P A 2
C1B C 0.298(2) 0.594(2) 0.5690(16) 0.050(3) Uani 0.18 1 d D U P A 2
H1B H 0.377723 0.555353 0.540450 0.060 Uiso 0.18 1 calc R U P A 2
C2B C 0.286(7) 0.719(3) 0.561(3) 0.12(3) Uani 0.18 1 d D . P A 2
H2B1 H 0.283466 0.757307 0.492456 0.179 Uiso 0.18 1 calc R U P A 2
H2B2 H 0.215911 0.760162 0.597518 0.179 Uiso 0.18 1 calc R U P A 2
H2B3 H 0.352073 0.718796 0.587006 0.179 Uiso 0.18 1 calc R U P A 2
C3B C 0.303(4) 0.536(3) 0.6765(19) 0.068(6) Uani 0.18 1 d D U P A 2
H3B1 H 0.310287 0.456392 0.683211 0.102 Uiso 0.18 1 calc R U P A 2
H3B2 H 0.368267 0.537114 0.702171 0.102 Uiso 0.18 1 calc R U P A 2
H3B3 H 0.232104 0.578479 0.712683 0.102 Uiso 0.18 1 calc R U P A 2
O1B O 0.1688(19) 0.7010(14) 0.4047(13) 0.042(4) Uani 0.18 1 d D . P A 2
H1B1 H 0.089375 0.747289 0.408812 0.051 Uiso 0.18 1 calc R U P A 2
O3B O 0.203(2) 0.928(2) 0.3637(18) 0.064(4) Uani 0.18 1 d D U P A 2
H3F H 0.230(16) 0.930(14) 0.413(14) 0.096 Uiso 0.18 1 d D U P E 2
H3G H 0.136(9) 0.977(18) 0.365(19) 0.096 Uiso 0.18 1 d D U P F 2
C4B C 0.0788(19) 0.543(2) 0.5516(19) 0.049(3) Uani 0.18 1 d D U P A 2
H4B H 0.111612 0.470178 0.600025 0.059 Uiso 0.18 1 calc R U P A 2
C5B C 0.016(2) 0.518(3) 0.484(3) 0.060(6) Uani 0.18 1 d D U P A 2
H5B1 H 0.070230 0.459019 0.448325 0.089 Uiso 0.18 1 calc R U P A 2
H5B2 H -0.041258 0.488955 0.522655 0.089 Uiso 0.18 1 calc R U P A 2
H5B3 H -0.022856 0.588423 0.438529 0.089 Uiso 0.18 1 calc R U P A 2
C6B C -0.004(2) 0.634(3) 0.608(3) 0.079(6) Uani 0.18 1 d D U P A 2
H6B1 H 0.037803 0.648910 0.651257 0.118 Uiso 0.18 1 calc R U P A 2
H6B2 H -0.042710 0.705010 0.563155 0.118 Uiso 0.18 1 calc R U P A 2
H6B3 H -0.061112 0.605541 0.647281 0.118 Uiso 0.18 1 calc R U P A 2
C7B C 0.2876(13) 0.4554(10) 0.4136(12) 0.0324(11) Uani 0.18 1 d DG . P A 2
C8B C 0.3605(13) 0.3601(13) 0.4728(8) 0.0401(13) Uani 0.18 1 d DG . P A 2
C9B C 0.4416(14) 0.2685(12) 0.4328(12) 0.0400(14) Uani 0.18 1 d G . P A 2
H9B H 0.491376 0.203276 0.473187 0.048 Uiso 0.18 1 calc R U P A 2
C10B C 0.4498(18) 0.2723(15) 0.3336(13) 0.0405(12) Uani 0.18 1 d G . P A 2
H10B H 0.505223 0.209673 0.306228 0.049 Uiso 0.18 1 calc R U P A 2
C11B C 0.377(2) 0.3677(17) 0.2744(8) 0.0340(14) Uani 0.18 1 d G . P A 2
H11B H 0.382536 0.370247 0.206655 0.041 Uiso 0.18 1 calc R U P A 2
C12B C 0.2958(18) 0.4592(12) 0.3145(11) 0.0318(9) Uani 0.18 1 d DG . P A 2
F8B F 0.363(2) 0.3443(19) 0.5649(11) 0.077(5) Uani 0.18 1 d D U P A 2
C13 C 0.2306(4) 0.5713(4) 0.2548(3) 0.0284(8) Uani 1 1 d D . . . .
N13 N 0.1198(3) 0.5925(3) 0.2480(3) 0.0279(7) Uani 1 1 d D . . . .
H13 H 0.0900(19) 0.542(2) 0.272(3) 0.035(14) Uiso 1 1 d D . . . .
O13 O 0.2786(3) 0.6357(3) 0.2095(2) 0.0341(7) Uani 1 1 d . . . . .
C14 C 0.0415(4) 0.6941(4) 0.1864(3) 0.0303(9) Uani 1 1 d D . . . .
H14 H 0.086813 0.739536 0.148159 0.036 Uiso 1 1 calc R U . . .
C15 C -0.0080(4) 0.6588(4) 0.1137(4) 0.0383(10) Uani 1 1 d . . . . .
H15 H -0.060765 0.731574 0.075416 0.046 Uiso 1 1 calc R U . . .
C16 C 0.0867(5) 0.5970(5) 0.0415(4) 0.0437(12) Uani 1 1 d . . . . .
H16A H 0.137980 0.522863 0.075861 0.066 Uiso 1 1 calc R U . . .
H16B H 0.130152 0.644986 0.010919 0.066 Uiso 1 1 calc R U . . .
H16C H 0.052294 0.583574 -0.008484 0.066 Uiso 1 1 calc R U . . .
C17 C -0.0774(5) 0.5868(5) 0.1611(5) 0.0466(12) Uani 1 1 d . . . . .
H17A H -0.027297 0.512387 0.196004 0.070 Uiso 1 1 calc R U . . .
H17B H -0.112279 0.574022 0.111179 0.070 Uiso 1 1 calc R U . . .
H17C H -0.137423 0.627546 0.206729 0.070 Uiso 1 1 calc R U . . .
C18 C -0.0526(4) 0.7715(4) 0.2486(3) 0.0315(9) Uani 1 1 d D . . . .
H18A H -0.108890 0.834441 0.206262 0.038 Uiso 1 1 calc R U . . .
H18B H -0.092760 0.725827 0.293320 0.038 Uiso 1 1 calc R U . . .
N18 N -0.0059(3) 0.8206(3) 0.3042(3) 0.0343(8) Uani 1 1 d D . . . .
H18 H 0.040(5) 0.849(4) 0.265(3) 0.058(19) Uiso 1 1 d D . . . .
C19 C -0.0867(4) 0.9047(4) 0.3569(4) 0.0353(10) Uani 1 1 d D . . . .
C20 C -0.1811(5) 0.8882(5) 0.4109(5) 0.0467(12) Uani 1 1 d . . . . .
H20 H -0.193019 0.820154 0.411898 0.056 Uiso 1 1 calc R U . . .
C21 C -0.2578(5) 0.9693(6) 0.4630(5) 0.0552(15) Uani 1 1 d . . . . .
H21 H -0.323316 0.957968 0.497841 0.066 Uiso 1 1 calc R U . . .
C22 C -0.2394(6) 1.0668(6) 0.4645(5) 0.0551(15) Uani 1 1 d . . . . .
H22 H -0.291604 1.122421 0.500707 0.066 Uiso 1 1 calc R U . . .
C23 C -0.1445(6) 1.0827(5) 0.4131(5) 0.0539(14) Uani 1 1 d . . . . .
H23 H -0.131339 1.149407 0.414288 0.065 Uiso 1 1 calc R U . . .
C24 C -0.0683(5) 1.0024(5) 0.3596(4) 0.0491(13) Uani 1 1 d . . . . .
H24 H -0.003187 1.014284 0.324573 0.059 Uiso 1 1 calc R U . . .
Si2 Si 0.45838(11) 0.94019(12) 0.14596(10) 0.0368(3) Uani 1 1 d D . . . .
O2 O 0.4297(3) 0.8241(3) 0.1704(2) 0.0321(7) Uani 1 1 d . . . . .
H2 H 0.439191 0.798680 0.119360 0.039(15) Uiso 1 1 calc R . . A 1
C25 C 0.5277(5) 0.9327(5) 0.2539(5) 0.0499(14) Uani 1 1 d . . . . .
H25 H 0.560777 0.993241 0.237773 0.060 Uiso 1 1 calc R U . . .
C26 C 0.4433(7) 0.9538(6) 0.3434(5) 0.067(2) Uani 1 1 d . . . . .
H26A H 0.415003 0.891468 0.363496 0.101 Uiso 1 1 calc R U . . .
H26B H 0.379058 1.027694 0.327687 0.101 Uiso 1 1 calc R U . . .
H26C H 0.481907 0.955865 0.396210 0.101 Uiso 1 1 calc R U . . .
C27 C 0.6257(5) 0.8135(7) 0.2792(5) 0.0656(19) Uani 1 1 d . . . . .
H27A H 0.656152 0.808467 0.339473 0.098 Uiso 1 1 calc R U . . .
H27B H 0.686663 0.804054 0.226544 0.098 Uiso 1 1 calc R U . . .
H27C H 0.596482 0.752552 0.287631 0.098 Uiso 1 1 calc R U . . .
C28 C 0.5445(5) 0.9382(5) 0.0226(4) 0.0367(12) Uani 0.82 1 d D U P G 1
H28 H 0.504498 0.917431 -0.019874 0.044 Uiso 0.82 1 calc R U P G 1
C29 C 0.5405(10) 1.0586(6) -0.0244(6) 0.056(2) Uani 0.82 1 d D . P G 1
H29A H 0.560648 1.090921 0.022097 0.083 Uiso 0.82 1 calc R U P G 1
H29B H 0.463302 1.108235 -0.043638 0.083 Uiso 0.82 1 calc R U P G 1
H29C H 0.595053 1.053974 -0.081731 0.083 Uiso 0.82 1 calc R U P G 1
C30 C 0.6650(7) 0.8483(9) 0.0251(8) 0.051(2) Uani 0.82 1 d D . P G 1
H30A H 0.702477 0.850171 -0.040781 0.076 Uiso 0.82 1 calc R U P G 1
H30B H 0.662892 0.771800 0.051094 0.076 Uiso 0.82 1 calc R U P G 1
H30C H 0.707688 0.864692 0.066508 0.076 Uiso 0.82 1 calc R U P G 1
C28B C 0.5552(15) 0.9920(17) 0.0513(11) 0.025(3) Uani 0.18 1 d D U P G 2
H28B H 0.576749 1.047419 0.073991 0.030 Uiso 0.18 1 calc R U P G 2
C29B C 0.488(2) 1.052(3) -0.0376(16) 0.036(7) Uani 0.18 1 d D . P G 2
H29D H 0.420861 1.119004 -0.022735 0.054 Uiso 0.18 1 calc R U P G 2
H29E H 0.536200 1.076314 -0.091217 0.054 Uiso 0.18 1 calc R U P G 2
H29F H 0.462634 0.997770 -0.056198 0.054 Uiso 0.18 1 calc R U P G 2
C30B C 0.660(3) 0.887(3) 0.034(3) 0.048(12) Uani 0.18 1 d D U P G 2
H30D H 0.700642 0.851410 0.093073 0.072 Uiso 0.18 1 calc R U P G 2
H30E H 0.637121 0.830890 0.016108 0.072 Uiso 0.18 1 calc R U P G 2
H30F H 0.710687 0.909434 -0.018912 0.072 Uiso 0.18 1 calc R U P G 2
C31 C 0.3152(4) 1.0675(4) 0.1393(4) 0.0361(10) Uani 1 1 d . . . . .
C32 C 0.3059(5) 1.1730(5) 0.1571(4) 0.0467(12) Uani 1 1 d . . . . .
F32 F 0.4040(3) 1.1853(3) 0.1622(3) 0.0585(9) Uani 1 1 d . . . . .
C33 C 0.2044(6) 1.2637(5) 0.1703(5) 0.0581(16) Uani 1 1 d . . . . .
H33 H 0.203448 1.332941 0.182856 0.070 Uiso 1 1 calc R U . . .
C34 C 0.1034(6) 1.2518(5) 0.1649(6) 0.0585(16) Uani 1 1 d . . . . .
H34 H 0.032123 1.312558 0.175546 0.070 Uiso 1 1 calc R U . . .
C35 C 0.1062(5) 1.1517(4) 0.1442(4) 0.0442(12) Uani 1 1 d . . . . .
H35 H 0.036944 1.144066 0.139527 0.053 Uiso 1 1 calc R U . . .
C36 C 0.2111(4) 1.0618(4) 0.1300(3) 0.0319(9) Uani 1 1 d . . . . .
C37 C 0.2073(3) 0.9577(4) 0.1043(3) 0.0307(9) Uani 1 1 d D . . . .
N37 N 0.2516(3) 0.9404(3) 0.0144(3) 0.0313(8) Uani 1 1 d D . . . .
H37 H 0.283(5) 0.985(3) -0.0245(18) 0.040(15) Uiso 1 1 d D . . . .
O37 O 0.1632(3) 0.8965(3) 0.1610(3) 0.0395(8) Uani 1 1 d . . . . .
C38 C 0.2532(4) 0.8494(4) -0.0303(4) 0.0366(10) Uani 1 1 d D . . . .
H38 H 0.214246 0.802481 0.016165 0.044 Uiso 1 1 calc R U . H 1
C39 C 0.1844(5) 0.9102(5) -0.1217(5) 0.0364(13) Uani 0.82 1 d D . P I 1
H39 H 0.213810 0.969538 -0.160313 0.044 Uiso 0.82 1 calc R U P I 1
C40 C 0.1948(6) 0.8285(6) -0.1868(5) 0.0492(16) Uani 0.82 1 d D . P I 1
H40A H 0.273743 0.797350 -0.214888 0.074 Uiso 0.82 1 calc R U P I 1
H40B H 0.143523 0.870534 -0.238973 0.074 Uiso 0.82 1 calc R U P I 1
H40C H 0.173777 0.765092 -0.148590 0.074 Uiso 0.82 1 calc R U P I 1
C41 C 0.0593(6) 0.9725(6) -0.0868(6) 0.0448(17) Uani 0.82 1 d D U P I 1
H41A H 0.014485 1.014955 -0.143038 0.067 Uiso 0.82 1 calc R U P I 1
H41B H 0.054433 1.026646 -0.046990 0.067 Uiso 0.82 1 calc R U P I 1
H41C H 0.028997 0.915827 -0.048225 0.067 Uiso 0.82 1 calc R U P I 1
C39B C 0.1571(14) 0.872(2) -0.0958(13) 0.027(5) Uani 0.18 1 d D U P I 2
H39B H 0.161085 0.797201 -0.106403 0.032 Uiso 0.18 1 calc R U P I 2
C40B C 0.194(2) 0.938(2) -0.1910(15) 0.034(5) Uani 0.18 1 d D U P I 2
H40D H 0.271700 0.891672 -0.213144 0.051 Uiso 0.18 1 calc R U P I 2
H40E H 0.141667 0.953616 -0.240154 0.051 Uiso 0.18 1 calc R U P I 2
H40F H 0.191086 1.011382 -0.180532 0.051 Uiso 0.18 1 calc R U P I 2
C41B C 0.036(2) 0.941(3) -0.058(3) 0.047(6) Uani 0.18 1 d D U P I 2
H41D H 0.015064 0.897038 0.002690 0.070 Uiso 0.18 1 calc R U P I 2
H41E H 0.031963 1.014638 -0.046639 0.070 Uiso 0.18 1 calc R U P I 2
H41F H -0.017455 0.956873 -0.106261 0.070 Uiso 0.18 1 calc R U P I 2
C42 C 0.3754(4) 0.7712(4) -0.0559(3) 0.0361(10) Uani 1 1 d D . . . .
H42A H 0.375165 0.717166 -0.094558 0.043 Uiso 1 1 calc R U . . .
H42B H 0.417096 0.818334 -0.095611 0.043 Uiso 1 1 calc R U . . .
N42 N 0.4335(3) 0.7057(3) 0.0325(3) 0.0294(8) Uani 1 1 d D . . . .
H42 H 0.3907(13) 0.674(3) 0.071(3) 0.029(13) Uiso 1 1 d D . . . .
C43 C 0.5484(4) 0.6252(4) 0.0212(3) 0.0283(8) Uani 1 1 d D . . . .
C44 C 0.5951(4) 0.5454(4) 0.1027(3) 0.0316(9) Uani 1 1 d . . . . .
H44 H 0.549699 0.544198 0.162515 0.038 Uiso 1 1 calc R U . . .
C45 C 0.7077(4) 0.4672(4) 0.0973(4) 0.0388(11) Uani 1 1 d . . . . .
H45 H 0.738833 0.412281 0.153239 0.047 Uiso 1 1 calc R U . . .
C46 C 0.7747(4) 0.4692(5) 0.0105(4) 0.0413(11) Uani 1 1 d . . . . .
H46 H 0.851968 0.416305 0.006704 0.050 Uiso 1 1 calc R U . . .
C47 C 0.7283(5) 0.5485(5) -0.0705(4) 0.0422(11) Uani 1 1 d . . . . .
H47 H 0.774085 0.549406 -0.130156 0.051 Uiso 1 1 calc R U . . .
C48 C 0.6159(4) 0.6271(4) -0.0664(3) 0.0358(10) Uani 1 1 d . . . . .
H48 H 0.585132 0.681619 -0.122579 0.043 Uiso 1 1 calc R U . . .
B51 B 0.7488(4) 0.2628(4) 0.7329(3) 0.0257(9) Uani 1 1 d D . . . .
C51 C 0.7262(6) 0.1456(3) 0.7231(4) 0.0265(11) Uani 0.81 1 d DG . P J 1
C52 C 0.6169(5) 0.1595(3) 0.7080(6) 0.0299(9) Uani 0.81 1 d G . P J 1
H52 H 0.559376 0.234789 0.693987 0.036 Uiso 0.81 1 calc R U P J 1
C53 C 0.5918(3) 0.0634(5) 0.7133(7) 0.0316(11) Uani 0.81 1 d G . P J 1
C54 C 0.6760(3) -0.0467(4) 0.7338(5) 0.0332(13) Uani 0.81 1 d G . P J 1
H54 H 0.658776 -0.112387 0.737480 0.040 Uiso 0.81 1 calc R U P J 1
C55 C 0.7853(3) -0.0607(3) 0.7489(3) 0.0331(12) Uani 0.81 1 d G . P J 1
C56 C 0.8104(4) 0.0355(4) 0.7435(3) 0.0289(12) Uani 0.81 1 d G . P J 1
H56 H 0.885128 0.025910 0.753827 0.035 Uiso 0.81 1 calc R U P J 1
C51B C 0.729(3) 0.1527(15) 0.709(2) 0.0265(11) Uani 0.19 1 d DG . P J 2
C52B C 0.621(2) 0.1506(18) 0.709(3) 0.0299(9) Uani 0.19 1 d G . P J 2
H52B H 0.555384 0.220170 0.706097 0.036 Uiso 0.19 1 calc R U P J 2
C53B C 0.6111(16) 0.047(2) 0.713(3) 0.0316(11) Uani 0.19 1 d G . P J 2
C54B C 0.7078(19) -0.0549(17) 0.717(2) 0.0332(13) Uani 0.19 1 d G . P J 2
H54B H 0.700690 -0.125839 0.720205 0.040 Uiso 0.19 1 calc R U P J 2
C55B C 0.8149(16) -0.0528(15) 0.7177(12) 0.0331(12) Uani 0.19 1 d G . P J 2
C56B C 0.825(2) 0.051(2) 0.7136(15) 0.0289(12) Uani 0.19 1 d G . P J 2
H56B H 0.898546 0.052384 0.713832 0.035 Uiso 0.19 1 calc R U P J 2
C57 C 0.4786(5) 0.0689(5) 0.7050(4) 0.0461(12) Uani 1 1 d . . . . .
C58 C 0.8781(6) -0.1768(6) 0.7709(5) 0.052(2) Uani 0.81 1 d D . P J 1
F51 F 0.9199(5) -0.1965(4) 0.8547(5) 0.0833(18) Uani 0.81 1 d D U P J 1
F52 F 0.9669(5) -0.1880(5) 0.7060(6) 0.101(3) Uani 0.81 1 d D U P J 1
F53 F 0.8455(5) -0.2628(5) 0.7751(6) 0.0719(18) Uani 0.81 1 d D U P J 1
C58B C 0.9008(18) -0.166(2) 0.7223(15) 0.048(8) Uani 0.19 1 d D U P J 2
F51B F 0.984(2) -0.1826(18) 0.775(2) 0.080(5) Uani 0.19 1 d D U P J 2
F52B F 0.955(2) -0.175(2) 0.6337(16) 0.096(6) Uani 0.19 1 d D U P J 2
F53B F 0.883(3) -0.263(3) 0.748(2) 0.080(6) Uani 0.19 1 d D U P J 2
F54 F 0.4463(4) -0.0037(5) 0.7757(4) 0.0976(19) Uani 1 1 d . . . . .
F55 F 0.4710(3) 0.0419(4) 0.6223(3) 0.0675(11) Uani 1 1 d . . . . .
F56 F 0.3992(3) 0.1733(4) 0.7080(4) 0.0707(12) Uani 1 1 d . . . . .
C59 C 0.6901(3) 0.2797(3) 0.8420(3) 0.0249(8) Uani 1 1 d . . . . .
C60 C 0.5754(4) 0.3513(4) 0.8582(3) 0.0271(8) Uani 1 1 d . . . . .
H60 H 0.532739 0.395872 0.803806 0.033 Uiso 1 1 calc R U . . .
C61 C 0.5218(4) 0.3597(4) 0.9502(3) 0.0277(8) Uani 1 1 d . . . . .
C62 C 0.5802(4) 0.2956(4) 1.0318(3) 0.0288(8) Uani 1 1 d . . . . .
H62 H 0.544035 0.302311 1.095177 0.035 Uiso 1 1 calc R U . . .
C63 C 0.6932(4) 0.2217(4) 1.0180(3) 0.0292(8) Uani 1 1 d . . . . .
C64 C 0.7468(3) 0.2139(4) 0.9252(3) 0.0259(8) Uani 1 1 d . . . . .
H64 H 0.824204 0.162276 0.918076 0.031 Uiso 1 1 calc R U . . .
C65 C 0.3971(4) 0.4347(4) 0.9623(3) 0.0336(9) Uani 1 1 d . . . . .
C66 C 0.7596(4) 0.1485(4) 1.1031(3) 0.0358(10) Uani 1 1 d D . . . .
F59 F 0.8541(4) 0.1635(5) 1.1024(3) 0.0655(14) Uani 0.82 1 d D U P K 1
F60 F 0.7910(6) 0.0377(4) 1.1037(4) 0.0840(19) Uani 0.82 1 d D U P K 1
F61 F 0.7027(4) 0.1689(6) 1.1862(3) 0.090(2) Uani 0.82 1 d D U P K 1
F59B F 0.8535(14) 0.0537(15) 1.0891(13) 0.067(5) Uani 0.18 1 d D U P K 2
F60B F 0.7002(15) 0.1043(16) 1.1746(13) 0.067(4) Uani 0.18 1 d D U P K 2
F61B F 0.8037(17) 0.1994(16) 1.1482(14) 0.078(5) Uani 0.18 1 d D U P K 2
F62 F 0.3710(3) 0.4838(3) 1.0395(2) 0.0498(8) Uani 1 1 d . . . . .
F63 F 0.3303(3) 0.3772(3) 0.9710(3) 0.0565(9) Uani 1 1 d . . . . .
F64 F 0.3631(3) 0.5226(3) 0.8872(2) 0.0560(9) Uani 1 1 d . . . . .
C67 C 0.6907(3) 0.3792(4) 0.6521(3) 0.0257(8) Uani 1 1 d . . . . .
C68 C 0.6793(4) 0.3760(4) 0.5571(3) 0.0324(9) Uani 1 1 d . . . . .
H68 H 0.699656 0.303455 0.539534 0.039 Uiso 1 1 calc R U . . .
C69 C 0.6389(5) 0.4766(4) 0.4875(3) 0.0384(11) Uani 1 1 d . . . . .
C70 C 0.6081(5) 0.5845(4) 0.5106(3) 0.0393(11) Uani 1 1 d . . . . .
H70 H 0.580225 0.653007 0.463320 0.047 Uiso 1 1 calc R U . . .
C71 C 0.6190(4) 0.5892(4) 0.6037(3) 0.0336(9) Uani 1 1 d D . . . .
C72 C 0.6600(4) 0.4887(4) 0.6728(3) 0.0284(8) Uani 1 1 d . . . . .
H72 H 0.667292 0.494734 0.736300 0.034 Uiso 1 1 calc R U . . .
F67 F 0.6345(6) 0.3712(4) 0.3757(3) 0.0894(17) Uani 1 1 d . . . . .
F68 F 0.7104(5) 0.4963(5) 0.3253(3) 0.0883(15) Uani 1 1 d . . . . .
F69 F 0.5307(5) 0.5517(4) 0.3506(3) 0.0794(13) Uani 1 1 d . . . . .
F70 F 0.5697(6) 0.7898(4) 0.5597(4) 0.0721(17) Uani 0.82 1 d D U P L 1
F71 F 0.6602(4) 0.7043(5) 0.6865(4) 0.0510(12) Uani 0.82 1 d D U P L 1
F72 F 0.4872(4) 0.7295(4) 0.6913(4) 0.0727(15) Uani 0.82 1 d D U P L 1
F70B F 0.6288(18) 0.7725(19) 0.5498(14) 0.046(4) Uani 0.18 1 d D U P M 2
F71B F 0.613(2) 0.707(3) 0.6981(15) 0.066(6) Uani 0.18 1 d D U P M 2
F72B F 0.4739(15) 0.765(2) 0.614(2) 0.083(5) Uani 0.18 1 d D U P M 2
C73 C 0.6299(7) 0.4714(6) 0.3864(4) 0.0579(17) Uani 1 1 d . . . . .
C74 C 0.5846(5) 0.7024(5) 0.6345(4) 0.0394(13) Uani 0.82 1 d D . P L 1
C74B C 0.5832(17) 0.7117(13) 0.6146(16) 0.0394(13) Uani 0.18 1 d D . P M 2
C75 C 0.8878(2) 0.2368(4) 0.7222(3) 0.0255(10) Uani 0.75 1 d DG U P J 1
C76 C 0.9569(3) 0.1763(3) 0.6513(3) 0.0238(12) Uani 0.75 1 d DG U P J 1
H76 H 0.924271 0.152466 0.609625 0.029 Uiso 0.75 1 calc R U P J 1
C77 C 1.0737(3) 0.1508(3) 0.6415(2) 0.0260(11) Uani 0.75 1 d DG U P J 1
C78 C 1.1214(3) 0.1857(3) 0.7025(3) 0.0274(12) Uani 0.75 1 d DG U P J 1
H78 H 1.201184 0.168248 0.695718 0.033 Uiso 0.75 1 calc R U P J 1
C79 C 1.0523(4) 0.2461(3) 0.7734(3) 0.0311(10) Uani 0.75 1 d G U P J 1
C80 C 0.9355(4) 0.2717(4) 0.7832(3) 0.0281(13) Uani 0.75 1 d G U P J 1
H80 H 0.888226 0.312970 0.831702 0.034 Uiso 0.75 1 calc R U P J 1
C81 C 1.1468(5) 0.0877(5) 0.5645(4) 0.0386(14) Uani 0.75 1 d D U P J 1
C82 C 1.1044(7) 0.2821(6) 0.8391(6) 0.0394(15) Uani 0.75 1 d D U P J 1
F75 F 1.1157(4) 0.0034(4) 0.5559(4) 0.0540(12) Uani 0.75 1 d D . P J 1
F76 F 1.1380(4) 0.1547(5) 0.4763(3) 0.0581(13) Uani 0.75 1 d D . P J 1
F77 F 1.2558(3) 0.0392(4) 0.5786(3) 0.0477(10) Uani 0.75 1 d D U P J 1
F78 F 1.2008(5) 0.1974(6) 0.8701(5) 0.0882(19) Uani 0.75 1 d D U P J 1
F79 F 1.0443(6) 0.2912(8) 0.9226(5) 0.095(2) Uani 0.75 1 d D U P J 1
F80 F 1.1383(10) 0.3641(7) 0.7993(5) 0.119(3) Uani 0.75 1 d D U P J 1
C75B C 0.8871(8) 0.2529(15) 0.7095(11) 0.0255(10) Uani 0.25 1 d DG U P J 2
C76B C 0.9530(8) 0.2140(11) 0.6277(9) 0.025(3) Uani 0.25 1 d DG U P J 2
H76B H 0.920632 0.194688 0.582560 0.030 Uiso 0.25 1 calc R U P J 2
C77B C 1.0663(7) 0.2032(9) 0.6120(7) 0.034(3) Uani 0.25 1 d DG U P J 2
C78B C 1.1137(8) 0.2314(9) 0.6781(8) 0.032(2) Uani 0.25 1 d DG U P J 2
H78B H 1.191096 0.223981 0.667353 0.039 Uiso 0.25 1 calc R U P J 2
C79B C 1.0478(12) 0.2703(9) 0.7599(7) 0.0311(10) Uani 0.25 1 d G U P J 2
C80B C 0.9345(11) 0.2811(13) 0.7756(9) 0.023(3) Uani 0.25 1 d G U P J 2
H80B H 0.889488 0.307788 0.831467 0.028 Uiso 0.25 1 calc R U P J 2
C81B C 1.1370(11) 0.1613(13) 0.5238(10) 0.042(3) Uani 0.25 1 d D U P J 2
C82B C 1.0944(14) 0.3000(13) 0.8336(15) 0.039(3) Uani 0.25 1 d D U P J 2
F75B F 1.165(2) 0.0504(15) 0.540(2) 0.125(11) Uani 0.25 1 d D U P J 2
F76B F 1.0808(16) 0.204(2) 0.4452(13) 0.103(7) Uani 0.25 1 d D U P J 2
F77B F 1.2318(11) 0.1802(16) 0.4993(13) 0.078(4) Uani 0.25 1 d D U P J 2
F78B F 1.2012(9) 0.2903(13) 0.8107(10) 0.047(2) Uani 0.25 1 d D U P J 2
F79B F 1.1017(16) 0.2299(12) 0.9224(10) 0.068(4) Uani 0.25 1 d D U P J 2
F80B F 1.0348(8) 0.4023(7) 0.8504(7) 0.0281(19) Uani 0.25 1 d D U P J 2


_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
Na1 O3 2.241(8) . ?
Na1 O13 2.279(8) . ?
Na1 O2 2.284(10) . ?
Na1 O37 2.441(8) . ?
Na1 C37 3.049(9) . ?
Na1 C13 3.114(9) . ?
Si1 O1 1.646(5) . ?
Si1 C4 1.882(7) . ?
Si1 C1 1.895(7) . ?
Si1 C7 1.944(3) . ?
C1 C3 1.523(9) . ?
C1 C2 1.528(9) . ?
C1 H1 1.0000 . ?
O1 H1A 0.846(15) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C6 1.518(9) . ?
C4 C5 1.526(9) . ?
C4 H4 1.0000 . ?
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 C8 1.3900 . ?
C7 C12 1.3900 . ?
C8 F8 1.304(4) . ?
C8 C9 1.3900 . ?
C9 C10 1.3900 . ?
C9 H9 0.9500 . ?
C10 C11 1.3900 . ?
C10 H10 0.9500 . ?
C11 C12 1.3900 . ?
C11 H11 0.9500 . ?
C12 C13 1.504(5) . ?
O3 H3D 0.840(14) . ?
O3 H3E 0.847(14) . ?
Na1B O37 2.21(4) . ?
Na1B O3B 2.253(15) . ?
Na1B O13 2.35(3) . ?
Na1B O1B 2.42(5) . ?
Na1B O2 2.43(5) . ?
Na1B C37 2.88(5) . ?
Si1B O1B 1.644(13) . ?
Si1B C4B 1.90(3) . ?
Si1B C1B 1.916(15) . ?
Si1B C7B 1.964(11) . ?
C1B C3B 1.533(14) . ?
C1B C2B 1.534(14) . ?
C1B H1B 1.0000 . ?
C2B H2B1 0.9800 . ?
C2B H2B2 0.9800 . ?
C2B H2B3 0.9800 . ?
C3B H3B1 0.9800 . ?
C3B H3B2 0.9800 . ?
C3B H3B3 0.9800 . ?
O1B H1B1 0.9500 . ?
O3B H3F 0.845(15) . ?
O3B H3G 0.846(15) . ?
C4B C6B 1.521(14) . ?
C4B C5B 1.524(14) . ?
C4B H4B 1.0000 . ?
C5B H5B1 0.9800 . ?
C5B H5B2 0.9800 . ?
C5B H5B3 0.9800 . ?
C6B H6B1 0.9800 . ?
C6B H6B2 0.9800 . ?
C6B H6B3 0.9800 . ?
C7B C8B 1.3900 . ?
C7B C12B 1.3900 . ?
C8B F8B 1.283(13) . ?
C8B C9B 1.3900 . ?
C9B C10B 1.3900 . ?
C9B H9B 0.9500 . ?
C10B C11B 1.3900 . ?
C10B H10B 0.9500 . ?
C11B C12B 1.3900 . ?
C11B H11B 0.9500 . ?
C12B C13 1.477(11) . ?
C13 O13 1.233(5) . ?
C13 N13 1.353(6) . ?
N13 C14 1.474(5) . ?
N13 H13 0.865(15) . ?
C14 C18 1.525(6) . ?
C14 C15 1.542(7) . ?
C14 H14 1.0000 . ?
C15 C17 1.515(8) . ?
C15 C16 1.536(7) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N18 1.452(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
N18 C19 1.427(6) . ?
N18 H18 0.875(15) . ?
C19 C24 1.388(7) . ?
C19 C20 1.389(7) . ?
C20 C21 1.382(8) . ?
C20 H20 0.9500 . ?
C21 C22 1.381(9) . ?
C21 H21 0.9500 . ?
C22 C23 1.378(9) . ?
C22 H22 0.9500 . ?
C23 C24 1.384(8) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
Si2 O2 1.634(4) . ?
Si2 C25 1.869(6) . ?
Si2 C28B 1.872(13) . ?
Si2 C31 1.902(5) . ?
Si2 C28 1.914(6) . ?
O2 H2 0.8400 . ?
C25 C26 1.529(11) . ?
C25 C27 1.547(9) . ?
C25 H25 1.0000 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C30 1.510(9) . ?
C28 C29 1.523(8) . ?
C28 H28 1.0000 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C28B C30B 1.513(14) . ?
C28B C29B 1.518(13) . ?
C28B H28B 1.0000 . ?
C29B H29D 0.9800 . ?
C29B H29E 0.9800 . ?
C29B H29F 0.9800 . ?
C30B H30D 0.9800 . ?
C30B H30E 0.9800 . ?
C30B H30F 0.9800 . ?
C31 C36 1.401(7) . ?
C31 C32 1.402(7) . ?
C32 F32 1.351(7) . ?
C32 C33 1.374(9) . ?
C33 C34 1.386(10) . ?
C33 H33 0.9500 . ?
C34 C35 1.381(8) . ?
C34 H34 0.9500 . ?
C35 C36 1.397(7) . ?
C35 H35 0.9500 . ?
C36 C37 1.499(6) . ?
C37 O37 1.227(5) . ?
C37 N37 1.343(6) . ?
N37 C38 1.460(6) . ?
N37 H37 0.868(15) . ?
C38 C42 1.521(7) . ?
C38 C39 1.557(7) . ?
C38 C39B 1.563(14) . ?
C38 H38 1.0000 . ?
C39 C40 1.520(8) . ?
C39 C41 1.533(8) . ?
C39 H39 1.0000 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C39B C41B 1.526(13) . ?
C39B C40B 1.530(12) . ?
C39B H39B 1.0000 . ?
C40B H40D 0.9800 . ?
C40B H40E 0.9800 . ?
C40B H40F 0.9800 . ?
C41B H41D 0.9800 . ?
C41B H41E 0.9800 . ?
C41B H41F 0.9800 . ?
C42 N42 1.465(6) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
N42 C43 1.428(5) . ?
N42 H42 0.864(15) . ?
C43 C44 1.387(6) . ?
C43 C48 1.397(6) . ?
C44 C45 1.389(7) . ?
C44 H44 0.9500 . ?
C45 C46 1.385(8) . ?
C45 H45 0.9500 . ?
C46 C47 1.380(8) . ?
C46 H46 0.9500 . ?
C47 C48 1.388(7) . ?
C47 H47 0.9500 . ?
C48 H48 0.9500 . ?
B51 C59 1.634(6) . ?
B51 C67 1.640(6) . ?
B51 C51B 1.664(13) . ?
B51 C75 1.666(6) . ?
B51 C51 1.697(6) . ?
B51 C75B 1.712(10) . ?
C51 C52 1.3900 . ?
C51 C56 1.3900 . ?
C52 C53 1.3900 . ?
C52 H52 0.9500 . ?
C53 C54 1.3900 . ?
C53 C57 1.452(7) . ?
C54 C55 1.3900 . ?
C54 H54 0.9500 . ?
C55 C56 1.3900 . ?
C55 C58 1.489(8) . ?
C56 H56 0.9500 . ?
C51B C52B 1.3900 . ?
C51B C56B 1.3900 . ?
C52B C53B 1.3900 . ?
C52B H52B 0.9500 . ?
C53B C54B 1.3900 . ?
C53B C57 1.629(19) . ?
C54B C55B 1.3900 . ?
C54B H54B 0.9500 . ?
C55B C56B 1.3900 . ?
C55B C58B 1.42(3) . ?
C56B H56B 0.9500 . ?
C57 F56 1.324(7) . ?
C57 F55 1.336(8) . ?
C57 F54 1.339(7) . ?
C58 F51 1.319(8) . ?
C58 F52 1.324(8) . ?
C58 F53 1.326(8) . ?
C58B F51B 1.324(14) . ?
C58B F53B 1.330(14) . ?
C58B F52B 1.344(14) . ?
C59 C64 1.400(6) . ?
C59 C60 1.400(6) . ?
C60 C61 1.382(6) . ?
C60 H60 0.9500 . ?
C61 C62 1.389(6) . ?
C61 C65 1.503(6) . ?
C62 C63 1.387(6) . ?
C62 H62 0.9500 . ?
C63 C64 1.391(6) . ?
C63 C66 1.495(6) . ?
C64 H64 0.9500 . ?
C65 F63 1.323(6) . ?
C65 F62 1.328(6) . ?
C65 F64 1.341(5) . ?
C66 F59 1.304(6) . ?
C66 F61 1.307(6) . ?
C66 F60 1.319(6) . ?
C66 F60B 1.329(11) . ?
C66 F61B 1.341(12) . ?
C66 F59B 1.352(12) . ?
C67 C72 1.398(6) . ?
C67 C68 1.398(6) . ?
C68 C69 1.396(6) . ?
C68 H68 0.9500 . ?
C69 C70 1.392(7) . ?
C69 C73 1.485(7) . ?
C70 C71 1.376(7) . ?
C70 H70 0.9500 . ?
C71 C72 1.392(6) . ?
C71 C74B 1.499(15) . ?
C71 C74 1.500(7) . ?
C72 H72 0.9500 . ?
F67 C73 1.318(7) . ?
F68 C73 1.330(9) . ?
F69 C73 1.360(9) . ?
F70 C74 1.328(6) . ?
F71 C74 1.329(6) . ?
F72 C74 1.336(6) . ?
F70B C74B 1.289(12) . ?
F71B C74B 1.290(12) . ?
F72B C74B 1.289(12) . ?
C75 C76 1.3900 . ?
C75 C80 1.3900 . ?
C76 C77 1.3900 . ?
C76 H76 0.9500 . ?
C77 C78 1.3900 . ?
C77 C81 1.486(6) . ?
C78 C79 1.3900 . ?
C78 H78 0.9500 . ?
C79 C80 1.3900 . ?
C79 C82 1.490(10) . ?
C80 H80 0.9500 . ?
C81 F77 1.310(7) . ?
C81 F76 1.336(7) . ?
C81 F75 1.342(7) . ?
C82 F80 1.281(8) . ?
C82 F79 1.308(8) . ?
C82 F78 1.332(8) . ?
C75B C76B 1.3900 . ?
C75B C80B 1.3900 . ?
C76B C77B 1.3900 . ?
C76B H76B 0.9500 . ?
C77B C78B 1.3900 . ?
C77B C81B 1.497(9) . ?
C78B C79B 1.3900 . ?
C78B H78B 0.9500 . ?
C79B C80B 1.3900 . ?
C79B C82B 1.49(3) . ?
C80B H80B 0.9500 . ?
C81B F75B 1.301(13) . ?
C81B F77B 1.316(12) . ?
C81B F76B 1.317(13) . ?
C82B F80B 1.287(14) . ?
C82B F78B 1.318(15) . ?
C82B F79B 1.360(14) . ?

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 Na1 O13 126.7(5) . . ?
O3 Na1 O2 128.8(4) . . ?
O13 Na1 O2 103.8(3) . . ?
O3 Na1 O37 110.0(3) . . ?
O13 Na1 O37 79.9(2) . . ?
O2 Na1 O37 84.6(3) . . ?
O3 Na1 C37 118.1(3) . . ?
O13 Na1 C37 91.2(3) . . ?
O2 Na1 C37 62.8(2) . . ?
O37 Na1 C37 22.53(14) . . ?
O3 Na1 C13 107.1(4) . . ?
O13 Na1 C13 19.61(15) . . ?
O2 Na1 C13 122.8(2) . . ?
O37 Na1 C13 87.3(2) . . ?
C37 Na1 C13 103.8(2) . . ?
O1 Si1 C4 115.7(3) . . ?
O1 Si1 C1 104.6(3) . . ?
C4 Si1 C1 112.6(3) . . ?
O1 Si1 C7 108.0(2) . . ?
C4 Si1 C7 108.9(2) . . ?
C1 Si1 C7 106.5(2) . . ?
C3 C1 C2 109.8(7) . . ?
C3 C1 Si1 112.5(4) . . ?
C2 C1 Si1 111.4(4) . . ?
C3 C1 H1 107.7 . . ?
C2 C1 H1 107.7 . . ?
Si1 C1 H1 107.7 . . ?
Si1 O1 H1A 118(8) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C6 C4 C5 111.0(7) . . ?
C6 C4 Si1 114.2(5) . . ?
C5 C4 Si1 113.2(5) . . ?
C6 C4 H4 105.9 . . ?
C5 C4 H4 105.9 . . ?
Si1 C4 H4 105.9 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 120.0 . . ?
C8 C7 Si1 113.1(2) . . ?
C12 C7 Si1 123.9(2) . . ?
F8 C8 C7 121.0(3) . . ?
F8 C8 C9 119.0(3) . . ?
C7 C8 C9 120.0 . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 120.0 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.0 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C7 120.0 . . ?
C11 C12 C13 114.3(3) . . ?
C7 C12 C13 125.0(3) . . ?
Na1 O3 H3D 128(3) . . ?
Na1 O3 H3E 123(3) . . ?
H3D O3 H3E 106(2) . . ?
O37 Na1B O3B 90.4(14) . . ?
O37 Na1B O13 83.4(12) . . ?
O3B Na1B O13 157(2) . . ?
O37 Na1B O1B 109.0(19) . . ?
O3B Na1B O1B 81.5(14) . . ?
O13 Na1B O1B 79.5(16) . . ?
O37 Na1B O2 86.5(16) . . ?
O3B Na1B O2 104.6(19) . . ?
O13 Na1B O2 97.4(10) . . ?
O1B Na1B O2 163.5(19) . . ?
O37 Na1B C37 23.5(6) . . ?
O3B Na1B C37 88.7(15) . . ?
O13 Na1B C37 94.1(12) . . ?
O1B Na1B C37 131.8(17) . . ?
O2 Na1B C37 64.3(11) . . ?
O1B Si1B C4B 115.2(12) . . ?
O1B Si1B C1B 105.3(12) . . ?
C4B Si1B C1B 114.8(12) . . ?
O1B Si1B C7B 106.0(9) . . ?
C4B Si1B C7B 103.2(10) . . ?
C1B Si1B C7B 112.1(11) . . ?
C3B C1B C2B 108.3(14) . . ?
C3B C1B Si1B 122(2) . . ?
C2B C1B Si1B 113(2) . . ?
C3B C1B H1B 103.9 . . ?
C2B C1B H1B 103.9 . . ?
Si1B C1B H1B 103.9 . . ?
C1B C2B H2B1 109.5 . . ?
C1B C2B H2B2 109.5 . . ?
H2B1 C2B H2B2 109.5 . . ?
C1B C2B H2B3 109.5 . . ?
H2B1 C2B H2B3 109.5 . . ?
H2B2 C2B H2B3 109.5 . . ?
C1B C3B H3B1 109.5 . . ?
C1B C3B H3B2 109.5 . . ?
H3B1 C3B H3B2 109.5 . . ?
C1B C3B H3B3 109.5 . . ?
H3B1 C3B H3B3 109.5 . . ?
H3B2 C3B H3B3 109.5 . . ?
Si1B O1B Na1B 133.8(15) . . ?
Si1B O1B H1B1 113.1 . . ?
Na1B O1B H1B1 113.1 . . ?
Na1B O3B H3F 126(2) . . ?
Na1B O3B H3G 126(2) . . ?
H3F O3B H3G 105(4) . . ?
C6B C4B C5B 110.5(15) . . ?
C6B C4B Si1B 112.8(15) . . ?
C5B C4B Si1B 112.7(15) . . ?
C6B C4B H4B 106.8 . . ?
C5B C4B H4B 106.8 . . ?
Si1B C4B H4B 106.8 . . ?
C4B C5B H5B1 109.5 . . ?
C4B C5B H5B2 109.5 . . ?
H5B1 C5B H5B2 109.5 . . ?
C4B C5B H5B3 109.5 . . ?
H5B1 C5B H5B3 109.5 . . ?
H5B2 C5B H5B3 109.5 . . ?
C4B C6B H6B1 109.5 . . ?
C4B C6B H6B2 109.5 . . ?
H6B1 C6B H6B2 109.5 . . ?
C4B C6B H6B3 109.5 . . ?
H6B1 C6B H6B3 109.5 . . ?
H6B2 C6B H6B3 109.5 . . ?
C8B C7B C12B 120.0 . . ?
C8B C7B Si1B 110.2(10) . . ?
C12B C7B Si1B 128.8(10) . . ?
F8B C8B C9B 113.0(16) . . ?
F8B C8B C7B 127.0(16) . . ?
C9B C8B C7B 120.0 . . ?
C10B C9B C8B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
C8B C9B H9B 120.0 . . ?
C9B C10B C11B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
C11B C10B H10B 120.0 . . ?
C10B C11B C12B 120.0 . . ?
C10B C11B H11B 120.0 . . ?
C12B C11B H11B 120.0 . . ?
C11B C12B C7B 120.0 . . ?
C11B C12B C13 122.7(13) . . ?
C7B C12B C13 116.3(12) . . ?
O13 C13 N13 123.6(4) . . ?
O13 C13 C12B 120.6(10) . . ?
N13 C13 C12B 115.6(10) . . ?
O13 C13 C12 121.3(4) . . ?
N13 C13 C12 115.1(4) . . ?
N13 C13 Na1 120.5(3) . . ?
C12 C13 Na1 110.8(3) . . ?
C13 N13 C14 124.9(4) . . ?
C13 N13 H13 122.7(10) . . ?
C14 N13 H13 111.7(9) . . ?
C13 O13 Na1 122.0(4) . . ?
C13 O13 Na1B 119.8(12) . . ?
N13 C14 C18 110.6(4) . . ?
N13 C14 C15 111.5(4) . . ?
C18 C14 C15 111.7(4) . . ?
N13 C14 H14 107.6 . . ?
C18 C14 H14 107.6 . . ?
C15 C14 H14 107.6 . . ?
C17 C15 C16 110.5(4) . . ?
C17 C15 C14 113.9(4) . . ?
C16 C15 C14 111.0(4) . . ?
C17 C15 H15 107.0 . . ?
C16 C15 H15 107.0 . . ?
C14 C15 H15 107.0 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N18 C18 C14 111.1(4) . . ?
N18 C18 H18A 109.4 . . ?
C14 C18 H18A 109.4 . . ?
N18 C18 H18B 109.4 . . ?
C14 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C19 N18 C18 116.4(4) . . ?
C19 N18 H18 111(2) . . ?
C18 N18 H18 108(2) . . ?
C24 C19 C20 118.6(5) . . ?
C24 C19 N18 120.0(4) . . ?
C20 C19 N18 121.3(4) . . ?
C21 C20 C19 121.0(5) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C22 C21 C20 120.0(6) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C21 119.5(5) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 120.7(5) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C19 120.3(5) . . ?
C23 C24 H24 119.9 . . ?
C19 C24 H24 119.9 . . ?
O2 Si2 C25 104.9(2) . . ?
O2 Si2 C28B 133.4(7) . . ?
C25 Si2 C28B 97.1(6) . . ?
O2 Si2 C31 106.35(19) . . ?
C25 Si2 C31 108.9(3) . . ?
C28B Si2 C31 104.3(6) . . ?
O2 Si2 C28 105.8(2) . . ?
C25 Si2 C28 118.6(3) . . ?
C31 Si2 C28 111.2(2) . . ?
Si2 O2 Na1 133.7(2) . . ?
Si2 O2 Na1B 129.0(7) . . ?
Si2 O2 H2 109.5 . . ?
Na1 O2 H2 109.5 . . ?
C26 C25 C27 108.5(5) . . ?
C26 C25 Si2 112.5(4) . . ?
C27 C25 Si2 110.6(5) . . ?
C26 C25 H25 108.4 . . ?
C27 C25 H25 108.4 . . ?
Si2 C25 H25 108.4 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C30 C28 C29 112.4(7) . . ?
C30 C28 Si2 114.1(5) . . ?
C29 C28 Si2 110.5(4) . . ?
C30 C28 H28 106.4 . . ?
C29 C28 H28 106.4 . . ?
Si2 C28 H28 106.4 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C30B C28B C29B 112.6(14) . . ?
C30B C28B Si2 107(2) . . ?
C29B C28B Si2 105.9(14) . . ?
C30B C28B H28B 110.5 . . ?
C29B C28B H28B 110.5 . . ?
Si2 C28B H28B 110.5 . . ?
C28B C29B H29D 109.5 . . ?
C28B C29B H29E 109.5 . . ?
H29D C29B H29E 109.5 . . ?
C28B C29B H29F 109.5 . . ?
H29D C29B H29F 109.5 . . ?
H29E C29B H29F 109.5 . . ?
C28B C30B H30D 109.5 . . ?
C28B C30B H30E 109.5 . . ?
H30D C30B H30E 109.5 . . ?
C28B C30B H30F 109.5 . . ?
H30D C30B H30F 109.5 . . ?
H30E C30B H30F 109.5 . . ?
C36 C31 C32 114.7(5) . . ?
C36 C31 Si2 124.9(4) . . ?
C32 C31 Si2 119.9(4) . . ?
F32 C32 C33 118.2(5) . . ?
F32 C32 C31 117.2(5) . . ?
C33 C32 C31 124.6(5) . . ?
C32 C33 C34 118.5(5) . . ?
C32 C33 H33 120.8 . . ?
C34 C33 H33 120.8 . . ?
C35 C34 C33 120.1(5) . . ?
C35 C34 H34 119.9 . . ?
C33 C34 H34 119.9 . . ?
C34 C35 C36 119.8(5) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 H35 120.1 . . ?
C35 C36 C31 122.2(4) . . ?
C35 C36 C37 116.7(4) . . ?
C31 C36 C37 121.1(4) . . ?
O37 C37 N37 123.6(4) . . ?
O37 C37 C36 121.5(4) . . ?
N37 C37 C36 114.8(4) . . ?
O37 C37 Na1B 45.8(10) . . ?
N37 C37 Na1B 123.8(6) . . ?
C36 C37 Na1B 102.6(7) . . ?
O37 C37 Na1 49.6(3) . . ?
N37 C37 Na1 119.3(3) . . ?
C36 C37 Na1 103.6(3) . . ?
C37 N37 C38 125.8(4) . . ?
C37 N37 H37 122.2(9) . . ?
C38 N37 H37 112.0(9) . . ?
C37 O37 Na1B 110.7(13) . . ?
C37 O37 Na1 107.8(4) . . ?
N37 C38 C42 110.5(4) . . ?
N37 C38 C39 106.8(4) . . ?
C42 C38 C39 111.9(4) . . ?
N37 C38 C39B 120.7(9) . . ?
C42 C38 C39B 119.5(9) . . ?
N37 C38 H38 109.2 . . ?
C42 C38 H38 109.2 . . ?
C39 C38 H38 109.2 . . ?
C40 C39 C41 110.9(6) . . ?
C40 C39 C38 113.6(5) . . ?
C41 C39 C38 107.6(5) . . ?
C40 C39 H39 108.2 . . ?
C41 C39 H39 108.2 . . ?
C38 C39 H39 108.2 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C39 C41 H41A 109.5 . . ?
C39 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C39 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C41B C39B C40B 111.5(13) . . ?
C41B C39B C38 115(2) . . ?
C40B C39B C38 101.7(13) . . ?
C41B C39B H39B 109.3 . . ?
C40B C39B H39B 109.3 . . ?
C38 C39B H39B 109.3 . . ?
C39B C40B H40D 109.5 . . ?
C39B C40B H40E 109.5 . . ?
H40D C40B H40E 109.5 . . ?
C39B C40B H40F 109.5 . . ?
H40D C40B H40F 109.5 . . ?
H40E C40B H40F 109.5 . . ?
C39B C41B H41D 109.5 . . ?
C39B C41B H41E 109.5 . . ?
H41D C41B H41E 109.5 . . ?
C39B C41B H41F 109.5 . . ?
H41D C41B H41F 109.5 . . ?
H41E C41B H41F 109.5 . . ?
N42 C42 C38 110.3(4) . . ?
N42 C42 H42A 109.6 . . ?
C38 C42 H42A 109.6 . . ?
N42 C42 H42B 109.6 . . ?
C38 C42 H42B 109.6 . . ?
H42A C42 H42B 108.1 . . ?
C43 N42 C42 117.5(4) . . ?
C43 N42 H42 111.8(17) . . ?
C42 N42 H42 108.6(17) . . ?
C44 C43 C48 119.5(4) . . ?
C44 C43 N42 117.7(4) . . ?
C48 C43 N42 122.8(4) . . ?
C43 C44 C45 120.5(4) . . ?
C43 C44 H44 119.8 . . ?
C45 C44 H44 119.8 . . ?
C46 C45 C44 120.0(4) . . ?
C46 C45 H45 120.0 . . ?
C44 C45 H45 120.0 . . ?
C47 C46 C45 119.5(4) . . ?
C47 C46 H46 120.3 . . ?
C45 C46 H46 120.3 . . ?
C46 C47 C48 121.2(5) . . ?
C46 C47 H47 119.4 . . ?
C48 C47 H47 119.4 . . ?
C47 C48 C43 119.3(4) . . ?
C47 C48 H48 120.3 . . ?
C43 C48 H48 120.3 . . ?
C59 B51 C67 111.3(3) . . ?
C59 B51 C51B 107.1(11) . . ?
C67 B51 C51B 109.8(10) . . ?
C59 B51 C75 112.5(3) . . ?
C67 B51 C75 106.0(3) . . ?
C59 B51 C51 100.9(4) . . ?
C67 B51 C51 115.1(4) . . ?
C75 B51 C51 111.2(4) . . ?
C59 B51 C75B 116.5(6) . . ?
C67 B51 C75B 98.0(6) . . ?
C51B B51 C75B 113.9(13) . . ?
C52 C51 C56 120.0 . . ?
C52 C51 B51 118.6(4) . . ?
C56 C51 B51 120.7(4) . . ?
C53 C52 C51 120.0 . . ?
C53 C52 H52 120.0 . . ?
C51 C52 H52 120.0 . . ?
C52 C53 C54 120.0 . . ?
C52 C53 C57 124.0(4) . . ?
C54 C53 C57 115.9(4) . . ?
C53 C54 C55 120.0 . . ?
C53 C54 H54 120.0 . . ?
C55 C54 H54 120.0 . . ?
C56 C55 C54 120.0 . . ?
C56 C55 C58 118.1(4) . . ?
C54 C55 C58 121.9(4) . . ?
C55 C56 C51 120.0 . . ?
C55 C56 H56 120.0 . . ?
C51 C56 H56 120.0 . . ?
C52B C51B C56B 120.0 . . ?
C52B C51B B51 123.7(18) . . ?
C56B C51B B51 114.5(18) . . ?
C51B C52B C53B 120.0 . . ?
C51B C52B H52B 120.0 . . ?
C53B C52B H52B 120.0 . . ?
C54B C53B C52B 120.0 . . ?
C54B C53B C57 129.6(16) . . ?
C52B C53B C57 110.3(17) . . ?
C55B C54B C53B 120.0 . . ?
C55B C54B H54B 120.0 . . ?
C53B C54B H54B 120.0 . . ?
C54B C55B C56B 120.0 . . ?
C54B C55B C58B 110.4(18) . . ?
C56B C55B C58B 129.6(18) . . ?
C55B C56B C51B 120.0 . . ?
C55B C56B H56B 120.0 . . ?
C51B C56B H56B 120.0 . . ?
F56 C57 F55 106.9(5) . . ?
F56 C57 F54 106.3(5) . . ?
F55 C57 F54 105.4(5) . . ?
F56 C57 C53 111.9(5) . . ?
F55 C57 C53 112.5(6) . . ?
F54 C57 C53 113.4(6) . . ?
F56 C57 C53B 118.6(9) . . ?
F55 C57 C53B 108.9(14) . . ?
F54 C57 C53B 110.0(15) . . ?
F51 C58 F52 104.7(7) . . ?
F51 C58 F53 105.7(6) . . ?
F52 C58 F53 108.2(6) . . ?
F51 C58 C55 112.8(5) . . ?
F52 C58 C55 111.3(5) . . ?
F53 C58 C55 113.5(6) . . ?
F51B C58B F53B 104.3(14) . . ?
F51B C58B F52B 102.5(14) . . ?
F53B C58B F52B 101.7(14) . . ?
F51B C58B C55B 111.7(17) . . ?
F53B C58B C55B 125(2) . . ?
F52B C58B C55B 108.8(16) . . ?
C64 C59 C60 115.7(4) . . ?
C64 C59 B51 122.2(4) . . ?
C60 C59 B51 121.6(3) . . ?
C61 C60 C59 122.5(4) . . ?
C61 C60 H60 118.8 . . ?
C59 C60 H60 118.8 . . ?
C60 C61 C62 120.9(4) . . ?
C60 C61 C65 119.7(4) . . ?
C62 C61 C65 119.3(4) . . ?
C63 C62 C61 117.9(4) . . ?
C63 C62 H62 121.1 . . ?
C61 C62 H62 121.1 . . ?
C62 C63 C64 121.0(4) . . ?
C62 C63 C66 120.3(4) . . ?
C64 C63 C66 118.7(4) . . ?
C63 C64 C59 122.0(4) . . ?
C63 C64 H64 119.0 . . ?
C59 C64 H64 119.0 . . ?
F63 C65 F62 107.0(4) . . ?
F63 C65 F64 106.3(4) . . ?
F62 C65 F64 105.0(4) . . ?
F63 C65 C61 112.6(4) . . ?
F62 C65 C61 112.7(4) . . ?
F64 C65 C61 112.6(4) . . ?
F59 C66 F61 106.4(5) . . ?
F59 C66 F60 105.6(5) . . ?
F61 C66 F60 107.5(5) . . ?
F60B C66 F61B 103.2(10) . . ?
F60B C66 F59B 101.7(10) . . ?
F61B C66 F59B 100.2(10) . . ?
F59 C66 C63 112.5(4) . . ?
F61 C66 C63 113.1(4) . . ?
F60 C66 C63 111.4(4) . . ?
F60B C66 C63 114.1(9) . . ?
F61B C66 C63 116.9(9) . . ?
F59B C66 C63 118.4(8) . . ?
C72 C67 C68 116.1(4) . . ?
C72 C67 B51 120.6(3) . . ?
C68 C67 B51 123.0(4) . . ?
C69 C68 C67 121.7(4) . . ?
C69 C68 H68 119.2 . . ?
C67 C68 H68 119.2 . . ?
C70 C69 C68 120.8(4) . . ?
C70 C69 C73 118.2(4) . . ?
C68 C69 C73 120.9(5) . . ?
C71 C70 C69 118.2(4) . . ?
C71 C70 H70 120.9 . . ?
C69 C70 H70 120.9 . . ?
C70 C71 C72 120.8(4) . . ?
C70 C71 C74B 110.6(10) . . ?
C72 C71 C74B 128.5(10) . . ?
C70 C71 C74 121.2(4) . . ?
C72 C71 C74 118.0(4) . . ?
C71 C72 C67 122.3(4) . . ?
C71 C72 H72 118.8 . . ?
C67 C72 H72 118.8 . . ?
F67 C73 F68 107.9(6) . . ?
F67 C73 F69 106.0(5) . . ?
F68 C73 F69 103.8(5) . . ?
F67 C73 C69 114.1(5) . . ?
F68 C73 C69 111.9(5) . . ?
F69 C73 C69 112.3(6) . . ?
F70 C74 F71 106.6(5) . . ?
F70 C74 F72 106.6(5) . . ?
F71 C74 F72 104.4(5) . . ?
F70 C74 C71 112.5(5) . . ?
F71 C74 C71 113.3(5) . . ?
F72 C74 C71 112.9(5) . . ?
F70B C74B F72B 107.5(14) . . ?
F70B C74B F71B 108.2(14) . . ?
F72B C74B F71B 108.4(14) . . ?
F70B C74B C71 115.4(16) . . ?
F72B C74B C71 110.8(16) . . ?
F71B C74B C71 106(2) . . ?
C76 C75 C80 120.0 . . ?
C76 C75 B51 118.3(3) . . ?
C80 C75 B51 121.7(3) . . ?
C77 C76 C75 120.0 . . ?
C77 C76 H76 120.0 . . ?
C75 C76 H76 120.0 . . ?
C76 C77 C78 120.0 . . ?
C76 C77 C81 119.7(3) . . ?
C78 C77 C81 120.3(3) . . ?
C79 C78 C77 120.0 . . ?
C79 C78 H78 120.0 . . ?
C77 C78 H78 120.0 . . ?
C80 C79 C78 120.0 . . ?
C80 C79 C82 120.4(4) . . ?
C78 C79 C82 119.6(4) . . ?
C79 C80 C75 120.0 . . ?
C79 C80 H80 120.0 . . ?
C75 C80 H80 120.0 . . ?
F77 C81 F76 106.5(5) . . ?
F77 C81 F75 106.5(5) . . ?
F76 C81 F75 104.4(5) . . ?
F77 C81 C77 114.3(5) . . ?
F76 C81 C77 113.0(5) . . ?
F75 C81 C77 111.4(4) . . ?
F80 C82 F79 116.7(9) . . ?
F80 C82 F78 102.0(8) . . ?
F79 C82 F78 98.7(7) . . ?
F80 C82 C79 115.1(6) . . ?
F79 C82 C79 111.3(6) . . ?
F78 C82 C79 111.2(6) . . ?
C76B C75B C80B 120.0 . . ?
C76B C75B B51 121.1(9) . . ?
C80B C75B B51 118.9(9) . . ?
C77B C76B C75B 120.0 . . ?
C77B C76B H76B 120.0 . . ?
C75B C76B H76B 120.0 . . ?
C78B C77B C76B 120.0 . . ?
C78B C77B C81B 120.1(5) . . ?
C76B C77B C81B 119.9(5) . . ?
C79B C78B C77B 120.0 . . ?
C79B C78B H78B 120.0 . . ?
C77B C78B H78B 120.0 . . ?
C78B C79B C80B 120.0 . . ?
C78B C79B C82B 122.3(10) . . ?
C80B C79B C82B 117.7(10) . . ?
C79B C80B C75B 120.0 . . ?
C79B C80B H80B 120.0 . . ?
C75B C80B H80B 120.0 . . ?
F75B C81B F77B 107.6(13) . . ?
F75B C81B F76B 106.1(13) . . ?
F77B C81B F76B 105.1(12) . . ?
F75B C81B C77B 107.1(16) . . ?
F77B C81B C77B 117.1(11) . . ?
F76B C81B C77B 113.2(12) . . ?
F80B C82B F78B 108.2(15) . . ?
F80B C82B F79B 104.7(14) . . ?
F78B C82B F79B 101.8(14) . . ?
F80B C82B C79B 113.0(12) . . ?
F78B C82B C79B 113.0(15) . . ?
F79B C82B C79B 115.2(13) . . ?

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 Si1 C1 C3 53.0(6) . . . . ?
C4 Si1 C1 C3 -73.5(6) . . . . ?
C7 Si1 C1 C3 167.2(5) . . . . ?
O1 Si1 C1 C2 -70.8(6) . . . . ?
C4 Si1 C1 C2 162.8(5) . . . . ?
C7 Si1 C1 C2 43.5(6) . . . . ?
O1 Si1 C4 C6 -52.3(7) . . . . ?
C1 Si1 C4 C6 67.9(7) . . . . ?
C7 Si1 C4 C6 -174.1(6) . . . . ?
O1 Si1 C4 C5 76.0(6) . . . . ?
C1 Si1 C4 C5 -163.8(5) . . . . ?
C7 Si1 C4 C5 -45.9(6) . . . . ?
C12 C7 C8 F8 -179.9(5) . . . . ?
Si1 C7 C8 F8 18.7(4) . . . . ?
C12 C7 C8 C9 0.0 . . . . ?
Si1 C7 C8 C9 -161.3(3) . . . . ?
F8 C8 C9 C10 179.9(5) . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C10 C11 C12 C7 0.0 . . . . ?
C10 C11 C12 C13 -170.5(4) . . . . ?
C8 C7 C12 C11 0.0 . . . . ?
Si1 C7 C12 C11 159.2(3) . . . . ?
C8 C7 C12 C13 169.4(4) . . . . ?
Si1 C7 C12 C13 -31.4(4) . . . . ?
C4B Si1B O1B Na1B -167.3(17) . . . . ?
C1B Si1B O1B Na1B 65(2) . . . . ?
C7B Si1B O1B Na1B -54(2) . . . . ?
O1B Si1B C4B C6B -61(2) . . . . ?
C1B Si1B C4B C6B 62(2) . . . . ?
C7B Si1B C4B C6B -176(2) . . . . ?
O1B Si1B C4B C5B 65(2) . . . . ?
C1B Si1B C4B C5B -172(2) . . . . ?
C7B Si1B C4B C5B -50(2) . . . . ?
C12B C7B C8B F8B -179.8(5) . . . . ?
Si1B C7B C8B F8B 10.7(13) . . . . ?
C12B C7B C8B C9B 0.0 . . . . ?
Si1B C7B C8B C9B -169.5(13) . . . . ?
F8B C8B C9B C10B 179.8(4) . . . . ?
C7B C8B C9B C10B 0.0 . . . . ?
C8B C9B C10B C11B 0.0 . . . . ?
C9B C10B C11B C12B 0.0 . . . . ?
C10B C11B C12B C7B 0.0 . . . . ?
C10B C11B C12B C13 168.4(17) . . . . ?
C8B C7B C12B C11B 0.0 . . . . ?
Si1B C7B C12B C11B 167.4(15) . . . . ?
C8B C7B C12B C13 -169.1(17) . . . . ?
Si1B C7B C12B C13 -1.8(16) . . . . ?
C11B C12B C13 O13 -68.7(13) . . . . ?
C7B C12B C13 O13 100.1(12) . . . . ?
C11B C12B C13 N13 106.3(12) . . . . ?
C7B C12B C13 N13 -84.9(11) . . . . ?
C11 C12 C13 O13 -54.5(5) . . . . ?
C7 C12 C13 O13 135.5(4) . . . . ?
C11 C12 C13 N13 123.1(3) . . . . ?
C7 C12 C13 N13 -46.8(5) . . . . ?
C11 C12 C13 Na1 -95.9(3) . . . . ?
C7 C12 C13 Na1 94.2(4) . . . . ?
O13 C13 N13 C14 -0.1(7) . . . . ?
C12B C13 N13 C14 -174.9(8) . . . . ?
C12 C13 N13 C14 -177.6(4) . . . . ?
Na1 C13 N13 C14 45.4(5) . . . . ?
N13 C13 O13 Na1 98.2(5) . . . . ?
C12 C13 O13 Na1 -84.4(5) . . . . ?
N13 C13 O13 Na1B 89.6(12) . . . . ?
C12B C13 O13 Na1B -95.9(14) . . . . ?
C13 N13 C14 C18 -113.1(5) . . . . ?
C13 N13 C14 C15 121.9(5) . . . . ?
N13 C14 C15 C17 61.0(5) . . . . ?
C18 C14 C15 C17 -63.3(5) . . . . ?
N13 C14 C15 C16 -64.4(5) . . . . ?
C18 C14 C15 C16 171.3(4) . . . . ?
N13 C14 C18 N18 65.3(5) . . . . ?
C15 C14 C18 N18 -169.9(4) . . . . ?
C14 C18 N18 C19 173.1(4) . . . . ?
C18 N18 C19 C24 -139.1(5) . . . . ?
C18 N18 C19 C20 44.7(7) . . . . ?
C24 C19 C20 C21 2.6(9) . . . . ?
N18 C19 C20 C21 178.9(6) . . . . ?
C19 C20 C21 C22 -2.1(10) . . . . ?
C20 C21 C22 C23 0.5(11) . . . . ?
C21 C22 C23 C24 0.4(11) . . . . ?
C22 C23 C24 C19 0.2(10) . . . . ?
C20 C19 C24 C23 -1.7(9) . . . . ?
N18 C19 C24 C23 -178.0(6) . . . . ?
C25 Si2 O2 Na1 70.5(4) . . . . ?
C31 Si2 O2 Na1 -44.8(4) . . . . ?
C28 Si2 O2 Na1 -163.3(4) . . . . ?
C25 Si2 O2 Na1B 77.2(13) . . . . ?
C28B Si2 O2 Na1B -167.3(15) . . . . ?
C31 Si2 O2 Na1B -38.1(13) . . . . ?
O2 Si2 C25 C26 -71.0(5) . . . . ?
C28B Si2 C25 C26 150.4(8) . . . . ?
C31 Si2 C25 C26 42.5(5) . . . . ?
C28 Si2 C25 C26 171.1(4) . . . . ?
O2 Si2 C25 C27 50.4(5) . . . . ?
C28B Si2 C25 C27 -88.2(8) . . . . ?
C31 Si2 C25 C27 164.0(4) . . . . ?
C28 Si2 C25 C27 -67.4(5) . . . . ?
O2 Si2 C28B C30B -35(2) . . . . ?
C25 Si2 C28B C30B 83.2(17) . . . . ?
C31 Si2 C28B C30B -165.1(17) . . . . ?
O2 Si2 C28B C29B 84.9(17) . . . . ?
C25 Si2 C28B C29B -156.6(15) . . . . ?
C31 Si2 C28B C29B -45.0(16) . . . . ?
C36 C31 C32 F32 -177.0(5) . . . . ?
Si2 C31 C32 F32 11.0(7) . . . . ?
C36 C31 C32 C33 3.5(9) . . . . ?
Si2 C31 C32 C33 -168.5(5) . . . . ?
F32 C32 C33 C34 179.8(6) . . . . ?
C31 C32 C33 C34 -0.6(11) . . . . ?
C32 C33 C34 C35 -1.7(11) . . . . ?
C33 C34 C35 C36 0.9(10) . . . . ?
C34 C35 C36 C31 2.2(9) . . . . ?
C34 C35 C36 C37 -178.0(5) . . . . ?
C32 C31 C36 C35 -4.2(7) . . . . ?
Si2 C31 C36 C35 167.3(4) . . . . ?
C32 C31 C36 C37 176.0(5) . . . . ?
Si2 C31 C36 C37 -12.5(7) . . . . ?
C35 C36 C37 O37 -64.4(6) . . . . ?
C31 C36 C37 O37 115.4(5) . . . . ?
C35 C36 C37 N37 113.2(5) . . . . ?
C31 C36 C37 N37 -67.0(6) . . . . ?
C35 C36 C37 Na1B -109.8(9) . . . . ?
C31 C36 C37 Na1B 70.0(9) . . . . ?
C35 C36 C37 Na1 -115.1(4) . . . . ?
C31 C36 C37 Na1 64.7(5) . . . . ?
O37 C37 N37 C38 0.9(7) . . . . ?
C36 C37 N37 C38 -176.6(4) . . . . ?
Na1B C37 N37 C38 56.7(12) . . . . ?
Na1 C37 N37 C38 59.7(5) . . . . ?
N37 C37 O37 Na1B 106.6(8) . . . . ?
C36 C37 O37 Na1B -76.1(8) . . . . ?
N37 C37 O37 Na1 101.8(4) . . . . ?
C36 C37 O37 Na1 -80.8(4) . . . . ?
C37 N37 C38 C42 -118.8(5) . . . . ?
C37 N37 C38 C39 119.2(5) . . . . ?
C37 N37 C38 C39B 94.6(10) . . . . ?
N37 C38 C39 C40 169.9(5) . . . . ?
C42 C38 C39 C40 48.9(7) . . . . ?
N37 C38 C39 C41 -66.9(6) . . . . ?
C42 C38 C39 C41 172.1(5) . . . . ?
N37 C38 C39B C41B -43(2) . . . . ?
C42 C38 C39B C41B 173.8(15) . . . . ?
N37 C38 C39B C40B 78.3(16) . . . . ?
C42 C38 C39B C40B -65.3(16) . . . . ?
N37 C38 C42 N42 67.5(5) . . . . ?
C39 C38 C42 N42 -173.6(4) . . . . ?
C39B C38 C42 N42 -145.5(10) . . . . ?
C38 C42 N42 C43 178.1(4) . . . . ?
C42 N42 C43 C44 -166.0(4) . . . . ?
C42 N42 C43 C48 16.8(6) . . . . ?
C48 C43 C44 C45 -0.5(7) . . . . ?
N42 C43 C44 C45 -177.9(4) . . . . ?
C43 C44 C45 C46 0.6(7) . . . . ?
C44 C45 C46 C47 -0.6(8) . . . . ?
C45 C46 C47 C48 0.5(8) . . . . ?
C46 C47 C48 C43 -0.4(8) . . . . ?
C44 C43 C48 C47 0.4(7) . . . . ?
N42 C43 C48 C47 177.6(4) . . . . ?
C59 B51 C51 C52 75.0(4) . . . . ?
C67 B51 C51 C52 -44.9(4) . . . . ?
C75 B51 C51 C52 -165.4(3) . . . . ?
C59 B51 C51 C56 -95.7(4) . . . . ?
C67 B51 C51 C56 144.3(4) . . . . ?
C75 B51 C51 C56 23.8(5) . . . . ?
C56 C51 C52 C53 0.0 . . . . ?
B51 C51 C52 C53 -170.8(4) . . . . ?
C51 C52 C53 C54 0.0 . . . . ?
C51 C52 C53 C57 175.8(7) . . . . ?
C52 C53 C54 C55 0.0 . . . . ?
C57 C53 C54 C55 -176.1(7) . . . . ?
C53 C54 C55 C56 0.0 . . . . ?
C53 C54 C55 C58 -179.9(3) . . . . ?
C54 C55 C56 C51 0.0 . . . . ?
C58 C55 C56 C51 179.9(3) . . . . ?
C52 C51 C56 C55 0.0 . . . . ?
B51 C51 C56 C55 170.7(4) . . . . ?
C59 B51 C51B C52B 59.7(14) . . . . ?
C67 B51 C51B C52B -61.3(14) . . . . ?
C75B B51 C51B C52B -170.1(13) . . . . ?
C59 B51 C51B C56B -104.9(13) . . . . ?
C67 B51 C51B C56B 134.1(10) . . . . ?
C75B B51 C51B C56B 25.3(17) . . . . ?
C56B C51B C52B C53B 0.0 . . . . ?
B51 C51B C52B C53B -163.8(18) . . . . ?
C51B C52B C53B C54B 0.0 . . . . ?
C51B C52B C53B C57 -176(3) . . . . ?
C52B C53B C54B C55B 0.0 . . . . ?
C57 C53B C54B C55B 176(3) . . . . ?
C53B C54B C55B C56B 0.0 . . . . ?
C53B C54B C55B C58B -179.9(4) . . . . ?
C54B C55B C56B C51B 0.0 . . . . ?
C58B C55B C56B C51B 179.9(5) . . . . ?
C52B C51B C56B C55B 0.0 . . . . ?
B51 C51B C56B C55B 165.2(17) . . . . ?
C52 C53 C57 F56 -10.5(7) . . . . ?
C54 C53 C57 F56 165.4(4) . . . . ?
C52 C53 C57 F55 109.8(5) . . . . ?
C54 C53 C57 F55 -74.2(6) . . . . ?
C52 C53 C57 F54 -130.7(5) . . . . ?
C54 C53 C57 F54 45.3(8) . . . . ?
C54B C53B C57 F56 175.9(13) . . . . ?
C52B C53B C57 F56 -8.1(19) . . . . ?
C54B C53B C57 F55 -62(2) . . . . ?
C52B C53B C57 F55 114.3(10) . . . . ?
C54B C53B C57 F54 53(2) . . . . ?
C52B C53B C57 F54 -130.7(10) . . . . ?
C56 C55 C58 F51 59.3(6) . . . . ?
C54 C55 C58 F51 -120.8(6) . . . . ?
C56 C55 C58 F52 -58.1(7) . . . . ?
C54 C55 C58 F52 121.8(7) . . . . ?
C56 C55 C58 F53 179.6(5) . . . . ?
C54 C55 C58 F53 -0.5(7) . . . . ?
C54B C55B C58B F51B -144(2) . . . . ?
C56B C55B C58B F51B 36(2) . . . . ?
C54B C55B C58B F53B -17(2) . . . . ?
C56B C55B C58B F53B 163(2) . . . . ?
C54B C55B C58B F52B 103.4(19) . . . . ?
C56B C55B C58B F52B -76(2) . . . . ?
C67 B51 C59 C64 -156.9(4) . . . . ?
C51B B51 C59 C64 83.1(11) . . . . ?
C75 B51 C59 C64 -38.0(6) . . . . ?
C51 B51 C59 C64 80.6(5) . . . . ?
C75B B51 C59 C64 -45.6(8) . . . . ?
C67 B51 C59 C60 30.8(5) . . . . ?
C51B B51 C59 C60 -89.2(11) . . . . ?
C75 B51 C59 C60 149.7(4) . . . . ?
C51 B51 C59 C60 -91.7(5) . . . . ?
C75B B51 C59 C60 142.0(7) . . . . ?
C64 C59 C60 C61 1.9(6) . . . . ?
B51 C59 C60 C61 174.7(4) . . . . ?
C59 C60 C61 C62 -0.5(7) . . . . ?
C59 C60 C61 C65 -177.6(4) . . . . ?
C60 C61 C62 C63 -1.2(7) . . . . ?
C65 C61 C62 C63 175.9(4) . . . . ?
C61 C62 C63 C64 1.4(7) . . . . ?
C61 C62 C63 C66 -178.6(4) . . . . ?
C62 C63 C64 C59 0.1(7) . . . . ?
C66 C63 C64 C59 -179.9(4) . . . . ?
C60 C59 C64 C63 -1.7(6) . . . . ?
B51 C59 C64 C63 -174.5(4) . . . . ?
C60 C61 C65 F63 92.4(5) . . . . ?
C62 C61 C65 F63 -84.7(5) . . . . ?
C60 C61 C65 F62 -146.4(4) . . . . ?
C62 C61 C65 F62 36.5(6) . . . . ?
C60 C61 C65 F64 -27.8(6) . . . . ?
C62 C61 C65 F64 155.1(4) . . . . ?
C62 C63 C66 F59 -124.8(5) . . . . ?
C64 C63 C66 F59 55.2(6) . . . . ?
C62 C63 C66 F61 -4.3(7) . . . . ?
C64 C63 C66 F61 175.8(5) . . . . ?
C62 C63 C66 F60 116.9(6) . . . . ?
C64 C63 C66 F60 -63.0(6) . . . . ?
C62 C63 C66 F60B 39.7(12) . . . . ?
C64 C63 C66 F60B -140.2(11) . . . . ?
C62 C63 C66 F61B -80.8(12) . . . . ?
C64 C63 C66 F61B 99.2(11) . . . . ?
C62 C63 C66 F59B 159.3(12) . . . . ?
C64 C63 C66 F59B -20.7(13) . . . . ?
C59 B51 C67 C72 39.0(5) . . . . ?
C51B B51 C67 C72 157.4(13) . . . . ?
C75 B51 C67 C72 -83.7(5) . . . . ?
C51 B51 C67 C72 152.9(4) . . . . ?
C75B B51 C67 C72 -83.6(7) . . . . ?
C59 B51 C67 C68 -147.5(4) . . . . ?
C51B B51 C67 C68 -29.1(13) . . . . ?
C75 B51 C67 C68 89.8(5) . . . . ?
C51 B51 C67 C68 -33.5(6) . . . . ?
C75B B51 C67 C68 89.9(7) . . . . ?
C72 C67 C68 C69 -0.4(7) . . . . ?
B51 C67 C68 C69 -174.2(4) . . . . ?
C67 C68 C69 C70 -0.1(8) . . . . ?
C67 C68 C69 C73 178.6(5) . . . . ?
C68 C69 C70 C71 0.3(8) . . . . ?
C73 C69 C70 C71 -178.5(6) . . . . ?
C69 C70 C71 C72 0.1(8) . . . . ?
C69 C70 C71 C74B 179.4(9) . . . . ?
C69 C70 C71 C74 -178.3(5) . . . . ?
C70 C71 C72 C67 -0.6(7) . . . . ?
C74B C71 C72 C67 -179.8(10) . . . . ?
C74 C71 C72 C67 177.8(4) . . . . ?
C68 C67 C72 C71 0.8(7) . . . . ?
B51 C67 C72 C71 174.7(4) . . . . ?
C70 C69 C73 F67 -165.0(6) . . . . ?
C68 C69 C73 F67 16.2(10) . . . . ?
C70 C69 C73 F68 72.1(8) . . . . ?
C68 C69 C73 F68 -106.7(6) . . . . ?
C70 C69 C73 F69 -44.2(8) . . . . ?
C68 C69 C73 F69 137.0(5) . . . . ?
C70 C71 C74 F70 -14.6(8) . . . . ?
C72 C71 C74 F70 166.9(5) . . . . ?
C70 C71 C74 F71 -135.6(5) . . . . ?
C72 C71 C74 F71 46.0(7) . . . . ?
C70 C71 C74 F72 106.1(6) . . . . ?
C72 C71 C74 F72 -72.4(7) . . . . ?
C70 C71 C74B F70B -50.4(18) . . . . ?
C72 C71 C74B F70B 128.9(15) . . . . ?
C70 C71 C74B F72B 72.1(15) . . . . ?
C72 C71 C74B F72B -108.6(15) . . . . ?
C70 C71 C74B F71B -170.3(12) . . . . ?
C72 C71 C74B F71B 8.9(17) . . . . ?
C59 B51 C75 C76 154.3(3) . . . . ?
C67 B51 C75 C76 -83.8(4) . . . . ?
C51 B51 C75 C76 42.0(4) . . . . ?
C59 B51 C75 C80 -24.3(4) . . . . ?
C67 B51 C75 C80 97.6(3) . . . . ?
C51 B51 C75 C80 -136.6(3) . . . . ?
C80 C75 C76 C77 0.0 . . . . ?
B51 C75 C76 C77 -178.7(4) . . . . ?
C75 C76 C77 C78 0.0 . . . . ?
C75 C76 C77 C81 -179.1(3) . . . . ?
C76 C77 C78 C79 0.0 . . . . ?
C81 C77 C78 C79 179.0(3) . . . . ?
C77 C78 C79 C80 0.0 . . . . ?
C77 C78 C79 C82 179.4(3) . . . . ?
C78 C79 C80 C75 0.0 . . . . ?
C82 C79 C80 C75 -179.4(3) . . . . ?
C76 C75 C80 C79 0.0 . . . . ?
B51 C75 C80 C79 178.6(4) . . . . ?
C76 C77 C81 F77 -161.1(4) . . . . ?
C78 C77 C81 F77 19.9(5) . . . . ?
C76 C77 C81 F76 76.9(5) . . . . ?
C78 C77 C81 F76 -102.1(5) . . . . ?
C76 C77 C81 F75 -40.3(5) . . . . ?
C78 C77 C81 F75 140.7(4) . . . . ?
C80 C79 C82 F80 -108.9(8) . . . . ?
C78 C79 C82 F80 71.7(8) . . . . ?
C80 C79 C82 F79 26.7(7) . . . . ?
C78 C79 C82 F79 -152.6(6) . . . . ?
C80 C79 C82 F78 135.8(6) . . . . ?
C78 C79 C82 F78 -43.6(6) . . . . ?
C59 B51 C75B C76B 165.9(5) . . . . ?
C67 B51 C75B C76B -75.4(8) . . . . ?
C51B B51 C75B C76B 40.5(14) . . . . ?
C59 B51 C75B C80B -12.0(9) . . . . ?
C67 B51 C75B C80B 106.7(6) . . . . ?
C51B B51 C75B C80B -137.4(11) . . . . ?
C80B C75B C76B C77B 0.0 . . . . ?
B51 C75B C76B C77B -177.9(11) . . . . ?
C75B C76B C77B C78B 0.0 . . . . ?
C75B C76B C77B C81B -179.9(4) . . . . ?
C76B C77B C78B C79B 0.0 . . . . ?
C81B C77B C78B C79B 179.9(4) . . . . ?
C77B C78B C79B C80B 0.0 . . . . ?
C77B C78B C79B C82B 179.1(4) . . . . ?
C78B C79B C80B C75B 0.0 . . . . ?
C82B C79B C80B C75B -179.1(4) . . . . ?
C76B C75B C80B C79B 0.0 . . . . ?
B51 C75B C80B C79B 177.9(11) . . . . ?
C78B C77B C81B F75B 104.0(13) . . . . ?
C76B C77B C81B F75B -76.1(13) . . . . ?
C78B C77B C81B F77B -16.9(13) . . . . ?
C76B C77B C81B F77B 163.1(13) . . . . ?
C78B C77B C81B F76B -139.4(13) . . . . ?
C76B C77B C81B F76B 40.5(13) . . . . ?
C78B C79B C82B F80B 126.2(12) . . . . ?
C80B C79B C82B F80B -54.8(12) . . . . ?
C78B C79B C82B F78B 2.8(11) . . . . ?
C80B C79B C82B F78B -178.1(11) . . . . ?
C78B C79B C82B F79B -113.5(13) . . . . ?
C80B C79B C82B F79B 65.5(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1A N13 0.846(15) 2.57(9) 3.151(6) 126(9) . yes
O1 H1A N18 0.846(15) 2.02(5) 2.795(6) 151(10) . yes
C9 H9 F55 0.95 2.59 3.360(5) 138.0 . yes
O3 H3D F75 0.840(14) 2.46(2) 3.239(6) 155(4) 1_465 yes
O3 H3E O1 0.847(14) 2.13(6) 2.718(7) 126(6) . yes
O1B H1B1 N18 0.95 1.90 2.58(2) 127. . yes
O3B H3F F75B 0.845(15) 2.48(6) 3.15(4) 136(6) 1_465 yes
C14 H14 O37 1.00 2.65 3.485(6) 142. . yes
C18 H18A F60 0.99 2.59 3.534(6) 159. 1_464 yes
N18 H18 O37 0.875(15) 2.157(16) 3.026(5) 172(2) . yes
C24 H24 O3B 0.95 2.53 3.23(3) 131. . yes
O2 H2 N42 0.84 1.95 2.752(5) 159. . yes
N42 H42 O13 0.864(15) 2.32(3) 3.136(5) 158(5) . yes
C48 H48 F71B 0.95 2.48 3.27(2) 140. 1_554 yes

_refine_diff_density_max         0.912
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.059

