# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_cu_d8v17582_0m
_database_code_depnum_ccdc_archive 'CCDC 1585539'
_audit_update_record             
;
2017-11-14 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H23 N O2'
_chemical_formula_weight         237.33

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'

_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                   7.7672(2)
_cell_length_b                   9.3611(3)
_cell_length_c                   19.2665(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1400.86(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4647
_cell_measurement_theta_min      11.392
_cell_measurement_theta_max      140.056

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.587
_shelx_estimated_absorpt_T_min   0.902
_shelx_estimated_absorpt_T_max   0.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5926
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            8103
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         6.594
_diffrn_reflns_theta_max         70.077
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             2596
_reflns_number_gt                2410
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_max     0.965
_reflns_Friedel_fraction_full    0.969

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0663P)²+0.1350P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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 947 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.16(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2596
_refine_ls_number_parameters     162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1238
_refine_ls_wR_factor_gt          0.1198
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1742(3) 0.1244(2) 0.42068(11) 0.0754(6) Uani 1 1 d . . . . .
O2 O 0.4548(2) 0.68952(17) 0.28870(10) 0.0627(5) Uani 1 1 d . . . . .
N1 N 0.3644(3) 0.30999(19) 0.32369(10) 0.0482(4) Uani 1 1 d . . . . .
C1 C 0.3097(4) 0.0599(2) 0.42088(12) 0.0586(6) Uani 1 1 d . . . . .
C2 C 0.3191(5) -0.0968(3) 0.4384(2) 0.0835(9) Uani 1 1 d . . . . .
H2A H 0.3505 -0.1503 0.3972 0.100 Uiso 1 1 calc R U . . .
H2B H 0.2067 -0.1296 0.4535 0.100 Uiso 1 1 calc R U . . .
C3 C 0.4494(5) -0.1254(3) 0.49490(17) 0.0844(9) Uani 1 1 d . . . . .
H3A H 0.4098 -0.0832 0.5380 0.101 Uiso 1 1 calc R U . . .
H3B H 0.4602 -0.2276 0.5019 0.101 Uiso 1 1 calc R U . . .
C4 C 0.6216(5) -0.0643(3) 0.47626(17) 0.0785(8) Uani 1 1 d . . . . .
H4A H 0.6660 -0.1133 0.4357 0.094 Uiso 1 1 calc R U . . .
H4B H 0.7013 -0.0801 0.5142 0.094 Uiso 1 1 calc R U . . .
C5 C 0.6103(4) 0.0961(3) 0.46111(16) 0.0759(8) Uani 1 1 d . . . . .
H5A H 0.7229 0.1306 0.4472 0.091 Uiso 1 1 calc R U . . .
H5B H 0.5777 0.1460 0.5032 0.091 Uiso 1 1 calc R U . . .
C6 C 0.4794(3) 0.1305(2) 0.40380(11) 0.0529(5) Uani 1 1 d . . . . .
H6 H 0.5220 0.0861 0.3610 0.063 Uiso 1 1 calc R U . . .
C7 C 0.4599(3) 0.2911(2) 0.38910(12) 0.0512(5) Uani 1 1 d . . . . .
H7 H 0.3942 0.3350 0.4269 0.061 Uiso 1 1 calc R U . . .
C8 C 0.6316(3) 0.3679(3) 0.38201(13) 0.0607(6) Uani 1 1 d . . . . .
H8A H 0.6994 0.3226 0.3459 0.073 Uiso 1 1 calc R U . . .
H8B H 0.6949 0.3607 0.4253 0.073 Uiso 1 1 calc R U . . .
C9 C 0.6035(4) 0.5255(3) 0.36392(13) 0.0617(6) Uani 1 1 d . . . . .
H9A H 0.5478 0.5730 0.4026 0.074 Uiso 1 1 calc R U . . .
H9B H 0.7142 0.5710 0.3565 0.074 Uiso 1 1 calc R U . . .
C10 C 0.4942(3) 0.5430(2) 0.29973(12) 0.0492(5) Uani 1 1 d . . . . .
H10 H 0.5579 0.5066 0.2595 0.059 Uiso 1 1 calc R U . . .
C11 C 0.3256(3) 0.4601(2) 0.30673(12) 0.0500(5) Uani 1 1 d . . . . .
H11 H 0.2577 0.5018 0.3445 0.060 Uiso 1 1 calc R U . . .
C12 C 0.2203(3) 0.4660(3) 0.23988(14) 0.0621(6) Uani 1 1 d . . . . .
H12A H 0.2110 0.5649 0.2252 0.075 Uiso 1 1 calc R U . . .
H12B H 0.2820 0.4146 0.2039 0.075 Uiso 1 1 calc R U . . .
C13 C 0.0442(4) 0.4050(4) 0.2460(2) 0.0873(10) Uani 1 1 d . . . . .
H13 H -0.0179 0.4349 0.2847 0.105 Uiso 1 1 calc R U . . .
C14 C -0.0306(6) 0.3221(6) 0.2082(3) 0.1312(19) Uani 1 1 d . . . . .
H14A H 0.0235 0.2876 0.1685 0.157 Uiso 1 1 calc R U . . .
H14B H -0.1420 0.2930 0.2188 0.157 Uiso 1 1 calc R U . . .
H1 H 0.273(4) 0.266(3) 0.3273(17) 0.066(9) Uiso 1 1 d . . . . .
H2 H 0.518(4) 0.722(3) 0.2542(18) 0.070(9) 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
O1 C1 1.213(3) . ?
O2 C10 1.421(3) . ?
N1 C7 1.473(3) . ?
N1 C11 1.474(3) . ?
C1 C2 1.508(3) . ?
C1 C6 1.510(4) . ?
C2 C3 1.510(5) . ?
C3 C4 1.498(5) . ?
C4 C5 1.532(4) . ?
C5 C6 1.535(4) . ?
C6 C7 1.538(3) . ?
C7 C8 1.521(3) . ?
C8 C9 1.532(3) . ?
C9 C10 1.509(3) . ?
C10 C11 1.528(3) . ?
C11 C12 1.527(3) . ?
C12 C13 1.487(4) . ?
C13 C14 1.213(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C11 114.03(17) . . ?
O1 C1 C2 121.8(3) . . ?
O1 C1 C6 122.6(2) . . ?
C2 C1 C6 115.6(3) . . ?
C1 C2 C3 111.5(3) . . ?
C4 C3 C2 111.0(2) . . ?
C3 C4 C5 111.7(3) . . ?
C4 C5 C6 112.3(2) . . ?
C1 C6 C5 109.2(2) . . ?
C1 C6 C7 112.4(2) . . ?
C5 C6 C7 113.8(2) . . ?
N1 C7 C8 107.93(18) . . ?
N1 C7 C6 108.95(18) . . ?
C8 C7 C6 113.1(2) . . ?
C7 C8 C9 110.5(2) . . ?
C10 C9 C8 111.8(2) . . ?
O2 C10 C9 110.39(18) . . ?
O2 C10 C11 108.56(18) . . ?
C9 C10 C11 110.77(18) . . ?
N1 C11 C12 109.34(19) . . ?
N1 C11 C10 109.15(18) . . ?
C12 C11 C10 111.48(18) . . ?
C13 C12 C11 114.3(2) . . ?
C14 C13 C12 129.7(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -127.2(3) . . . . ?
C6 C1 C2 C3 52.7(3) . . . . ?
C1 C2 C3 C4 -53.8(4) . . . . ?
C2 C3 C4 C5 56.4(4) . . . . ?
C3 C4 C5 C6 -56.1(4) . . . . ?
O1 C1 C6 C5 129.3(3) . . . . ?
C2 C1 C6 C5 -50.7(3) . . . . ?
O1 C1 C6 C7 2.0(3) . . . . ?
C2 C1 C6 C7 -178.0(2) . . . . ?
C4 C5 C6 C1 51.3(3) . . . . ?
C4 C5 C6 C7 177.8(2) . . . . ?
C11 N1 C7 C8 -61.4(2) . . . . ?
C11 N1 C7 C6 175.49(19) . . . . ?
C1 C6 C7 N1 -68.2(2) . . . . ?
C5 C6 C7 N1 166.9(2) . . . . ?
C1 C6 C7 C8 171.76(19) . . . . ?
C5 C6 C7 C8 46.9(3) . . . . ?
N1 C7 C8 C9 56.6(2) . . . . ?
C6 C7 C8 C9 177.2(2) . . . . ?
C7 C8 C9 C10 -55.0(3) . . . . ?
C8 C9 C10 O2 173.6(2) . . . . ?
C8 C9 C10 C11 53.3(3) . . . . ?
C7 N1 C11 C12 -177.60(19) . . . . ?
C7 N1 C11 C10 60.2(2) . . . . ?
O2 C10 C11 N1 -175.57(18) . . . . ?
C9 C10 C11 N1 -54.2(2) . . . . ?
O2 C10 C11 C12 63.5(2) . . . . ?
C9 C10 C11 C12 -175.1(2) . . . . ?
N1 C11 C12 C13 67.3(3) . . . . ?
C10 C11 C12 C13 -171.9(3) . . . . ?
C11 C12 C13 C14 -132.9(5) . . . . ?

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.027

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_d8v17583_0m
_database_code_depnum_ccdc_archive 'CCDC 1585542'
_audit_update_record             
;
2017-11-14 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H43 N O4 Si'
_chemical_formula_weight         473.71

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   33.6160(19)
_cell_length_b                   7.9053(4)
_cell_length_c                   11.1852(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.380(2)
_cell_angle_gamma                90
_cell_volume                     2971.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9927
_cell_measurement_theta_min      4.848
_cell_measurement_theta_max      52.208

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.059
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6943
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            34676
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.424
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             5776
_reflns_number_gt                4928
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.989

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0892P)²+0.3646P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2020 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.04(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5776
_refine_ls_number_parameters     307
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1375
_refine_ls_wR_factor_gt          0.1270
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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 0.75548(3) 0.24232(12) 0.76192(9) 0.0786(3) Uani 1 1 d . . . . .
N1 N 0.61327(6) 0.3742(3) 0.72045(19) 0.0619(6) Uani 1 1 d . . . . .
O1 O 0.72167(6) 0.3428(3) 0.6809(2) 0.0832(6) Uani 1 1 d . . . . .
O2 O 0.54654(12) 0.3859(3) 0.3997(3) 0.1213(12) Uani 1 1 d . . . . .
O3 O 0.55202(6) 0.3272(4) 0.79267(19) 0.0840(7) Uani 1 1 d . . . . .
O4 O 0.60586(5) 0.3449(4) 0.91662(16) 0.0752(6) Uani 1 1 d . . . . .
C1 C 0.59697(9) 0.3614(4) 0.5966(2) 0.0638(6) Uani 1 1 d . . . . .
H1 H 0.5722 0.2967 0.6005 0.077 Uiso 1 1 calc R U . . .
C2 C 0.62537(11) 0.2582(5) 0.5203(3) 0.0796(8) Uani 1 1 d . . . . .
H2A H 0.6228 0.1395 0.5407 0.095 Uiso 1 1 calc R U . . .
H2B H 0.6175 0.2711 0.4367 0.095 Uiso 1 1 calc R U . . .
C3 C 0.66864(11) 0.3098(5) 0.5364(3) 0.0834(9) Uani 1 1 d . . . . .
H3A H 0.6853 0.2354 0.4901 0.100 Uiso 1 1 calc R U . . .
H3B H 0.6722 0.4245 0.5078 0.100 Uiso 1 1 calc R U . . .
C4 C 0.68057(9) 0.2994(4) 0.6653(3) 0.0746(8) Uani 1 1 d . . . . .
H4 H 0.6769 0.1826 0.6922 0.089 Uiso 1 1 calc R U . . .
C5 C 0.65545(8) 0.4155(4) 0.7432(3) 0.0666(7) Uani 1 1 d . . . . .
H5 H 0.6617 0.3871 0.8269 0.080 Uiso 1 1 calc R U . . .
C6 C 0.66537(9) 0.6042(4) 0.7263(3) 0.0747(8) Uani 1 1 d . . . . .
H6A H 0.6938 0.6200 0.7392 0.090 Uiso 1 1 calc R U . . .
H6B H 0.6590 0.6358 0.6443 0.090 Uiso 1 1 calc R U . . .
C7 C 0.64396(13) 0.7186(5) 0.8074(4) 0.0988(12) Uani 1 1 d . . . . .
H7 H 0.6440 0.6878 0.8876 0.119 Uiso 1 1 calc R U . . .
C8 C 0.62553(19) 0.8535(8) 0.7804(7) 0.146(2) Uani 1 1 d . . . . .
H8A H 0.6244 0.8907 0.7015 0.175 Uiso 1 1 calc R U . . .
H8B H 0.6131 0.9155 0.8395 0.175 Uiso 1 1 calc R U . . .
C9 C 0.58625(9) 0.5334(3) 0.5429(3) 0.0626(6) Uani 1 1 d . . . . .
H9A H 0.5756 0.6049 0.6049 0.075 Uiso 1 1 calc R U . . .
H9B H 0.6102 0.5867 0.5145 0.075 Uiso 1 1 calc R U . . .
C10 C 0.55624(10) 0.5218(4) 0.4408(3) 0.0686(7) Uani 1 1 d . . . . .
C11 C 0.53838(9) 0.6787(4) 0.3897(2) 0.0621(6) Uani 1 1 d . . . . .
C12 C 0.55076(11) 0.8390(4) 0.4253(3) 0.0803(8) Uani 1 1 d . . . . .
H12 H 0.5709 0.8508 0.4831 0.096 Uiso 1 1 calc R U . . .
C13 C 0.53333(15) 0.9800(5) 0.3753(5) 0.1019(13) Uani 1 1 d . . . . .
H13 H 0.5421 1.0867 0.3988 0.122 Uiso 1 1 calc R U . . .
C14 C 0.50351(14) 0.9660(5) 0.2923(4) 0.0989(13) Uani 1 1 d . . . . .
H14 H 0.4915 1.0625 0.2605 0.119 Uiso 1 1 calc R U . . .
C15 C 0.49098(12) 0.8070(6) 0.2551(3) 0.0934(11) Uani 1 1 d . . . . .
H15 H 0.4709 0.7969 0.1968 0.112 Uiso 1 1 calc R U . . .
C16 C 0.50821(10) 0.6638(5) 0.3040(3) 0.0753(8) Uani 1 1 d . . . . .
H16 H 0.4996 0.5573 0.2795 0.090 Uiso 1 1 calc R U . . .
C17 C 0.58717(7) 0.3471(4) 0.8094(2) 0.0610(6) Uani 1 1 d . . . . .
C18 C 0.58323(10) 0.3312(8) 1.0264(3) 0.0996(13) Uani 1 1 d . . . . .
C19 C 0.61654(17) 0.3342(13) 1.1215(4) 0.155(3) Uani 1 1 d . . . . .
H19A H 0.6368 0.2548 1.1005 0.232 Uiso 1 1 calc R U . . .
H19B H 0.6060 0.3038 1.1975 0.232 Uiso 1 1 calc R U . . .
H19C H 0.6278 0.4457 1.1263 0.232 Uiso 1 1 calc R U . . .
C20 C 0.5579(2) 0.4851(13) 1.0362(6) 0.179(4) Uani 1 1 d . . . . .
H20A H 0.5745 0.5840 1.0367 0.268 Uiso 1 1 calc R U . . .
H20B H 0.5434 0.4803 1.1090 0.268 Uiso 1 1 calc R U . . .
H20C H 0.5395 0.4900 0.9692 0.268 Uiso 1 1 calc R U . . .
C21 C 0.5613(2) 0.1711(13) 1.0295(6) 0.174(3) Uani 1 1 d . . . . .
H21A H 0.5420 0.1682 0.9648 0.261 Uiso 1 1 calc R U . . .
H21B H 0.5479 0.1618 1.1041 0.261 Uiso 1 1 calc R U . . .
H21C H 0.5795 0.0785 1.0218 0.261 Uiso 1 1 calc R U . . .
C22 C 0.75645(17) 0.0143(6) 0.7232(7) 0.1256(17) Uani 1 1 d . . . . .
H22A H 0.7337 -0.0407 0.7557 0.188 Uiso 1 1 calc R U . . .
H22B H 0.7803 -0.0361 0.7560 0.188 Uiso 1 1 calc R U . . .
H22C H 0.7559 0.0017 0.6378 0.188 Uiso 1 1 calc R U . . .
C23 C 0.7436(2) 0.2639(10) 0.9231(4) 0.150(2) Uani 1 1 d . . . . .
H23A H 0.7382 0.3804 0.9408 0.225 Uiso 1 1 calc R U . . .
H23B H 0.7658 0.2256 0.9714 0.225 Uiso 1 1 calc R U . . .
H23C H 0.7206 0.1969 0.9400 0.225 Uiso 1 1 calc R U . . .
C24 C 0.80261(11) 0.3551(6) 0.7227(4) 0.0955(11) Uani 1 1 d . . . . .
C25 C 0.80988(18) 0.3361(8) 0.5893(5) 0.141(2) Uani 1 1 d . . . . .
H25A H 0.8347 0.3888 0.5704 0.211 Uiso 1 1 calc R U . . .
H25B H 0.7886 0.3895 0.5445 0.211 Uiso 1 1 calc R U . . .
H25C H 0.8109 0.2182 0.5691 0.211 Uiso 1 1 calc R U . . .
C26 C 0.8372(2) 0.2879(17) 0.7983(12) 0.265(7) Uani 1 1 d . . . . .
H26A H 0.8618 0.3256 0.7654 0.397 Uiso 1 1 calc R U . . .
H26B H 0.8365 0.1665 0.7985 0.397 Uiso 1 1 calc R U . . .
H26C H 0.8352 0.3290 0.8786 0.397 Uiso 1 1 calc R U . . .
C27 C 0.79790(17) 0.5454(7) 0.7460(5) 0.1221(17) Uani 1 1 d . . . . .
H27A H 0.7881 0.5625 0.8250 0.183 Uiso 1 1 calc R U . . .
H27B H 0.7794 0.5925 0.6883 0.183 Uiso 1 1 calc R U . . .
H27C H 0.8232 0.6002 0.7394 0.183 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si1 O1 1.641(3) . ?
Si1 C22 1.854(5) . ?
Si1 C23 1.864(5) . ?
Si1 C24 1.879(4) . ?
N1 C17 1.359(3) . ?
N1 C5 1.471(4) . ?
N1 C1 1.481(3) . ?
O1 C4 1.430(4) . ?
O2 C10 1.211(4) . ?
O3 C17 1.202(3) . ?
O4 C17 1.340(3) . ?
O4 C18 1.464(3) . ?
C1 C9 1.527(4) . ?
C1 C2 1.531(4) . ?
C1 H1 0.9800 . ?
C2 C3 1.517(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.489(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.533(4) . ?
C4 H4 0.9800 . ?
C5 C6 1.541(5) . ?
C5 H5 0.9800 . ?
C6 C7 1.480(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.266(8) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9300 . ?
C8 H8B 0.9300 . ?
C9 C10 1.508(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.486(4) . ?
C11 C16 1.384(5) . ?
C11 C12 1.389(5) . ?
C12 C13 1.372(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.354(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.387(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C18 C21 1.466(9) . ?
C18 C20 1.490(9) . ?
C18 C19 1.526(6) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C26 1.517(8) . ?
C24 C25 1.525(7) . ?
C24 C27 1.536(7) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Si1 C22 110.9(2) . . ?
O1 Si1 C23 109.1(3) . . ?
C22 Si1 C23 108.7(3) . . ?
O1 Si1 C24 102.60(15) . . ?
C22 Si1 C24 112.8(2) . . ?
C23 Si1 C24 112.6(3) . . ?
C17 N1 C5 123.0(2) . . ?
C17 N1 C1 116.3(2) . . ?
C5 N1 C1 120.7(2) . . ?
C4 O1 Si1 127.3(2) . . ?
C17 O4 C18 120.6(2) . . ?
N1 C1 C9 112.7(2) . . ?
N1 C1 C2 109.7(2) . . ?
C9 C1 C2 113.6(2) . . ?
N1 C1 H1 106.8 . . ?
C9 C1 H1 106.8 . . ?
C2 C1 H1 106.8 . . ?
C3 C2 C1 113.6(3) . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C4 C3 C2 109.6(3) . . ?
C4 C3 H3A 109.8 . . ?
C2 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
C2 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
O1 C4 C3 110.0(3) . . ?
O1 C4 C5 109.3(3) . . ?
C3 C4 C5 112.2(3) . . ?
O1 C4 H4 108.4 . . ?
C3 C4 H4 108.4 . . ?
C5 C4 H4 108.4 . . ?
N1 C5 C4 108.1(2) . . ?
N1 C5 C6 113.8(3) . . ?
C4 C5 C6 112.7(2) . . ?
N1 C5 H5 107.3 . . ?
C4 C5 H5 107.3 . . ?
C6 C5 H5 107.3 . . ?
C7 C6 C5 114.0(3) . . ?
C7 C6 H6A 108.8 . . ?
C5 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C8 C7 C6 127.7(5) . . ?
C8 C7 H7 116.2 . . ?
C6 C7 H7 116.2 . . ?
C7 C8 H8A 120.0 . . ?
C7 C8 H8B 120.0 . . ?
H8A C8 H8B 120.0 . . ?
C10 C9 C1 113.0(2) . . ?
C10 C9 H9A 109.0 . . ?
C1 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C1 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
O2 C10 C11 119.5(3) . . ?
O2 C10 C9 120.7(3) . . ?
C11 C10 C9 119.8(2) . . ?
C16 C11 C12 119.0(3) . . ?
C16 C11 C10 118.6(3) . . ?
C12 C11 C10 122.4(3) . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 121.0(4) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 119.6(3) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 120.2(4) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C11 119.9(4) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
O3 C17 O4 125.1(2) . . ?
O3 C17 N1 123.8(2) . . ?
O4 C17 N1 111.1(2) . . ?
C21 C18 O4 110.9(4) . . ?
C21 C18 C20 114.5(5) . . ?
O4 C18 C20 108.1(5) . . ?
C21 C18 C19 111.0(6) . . ?
O4 C18 C19 101.3(3) . . ?
C20 C18 C19 110.3(6) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Si1 C22 H22A 109.5 . . ?
Si1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
Si1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
Si1 C23 H23A 109.5 . . ?
Si1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
Si1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C26 C24 C25 111.8(7) . . ?
C26 C24 C27 109.2(7) . . ?
C25 C24 C27 106.4(4) . . ?
C26 C24 Si1 110.1(4) . . ?
C25 C24 Si1 109.7(3) . . ?
C27 C24 Si1 109.5(3) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
C22 Si1 O1 C4 52.3(3) . . . . ?
C23 Si1 O1 C4 -67.5(4) . . . . ?
C24 Si1 O1 C4 172.9(3) . . . . ?
C17 N1 C1 C9 97.5(3) . . . . ?
C5 N1 C1 C9 -82.1(3) . . . . ?
C17 N1 C1 C2 -135.0(3) . . . . ?
C5 N1 C1 C2 45.4(3) . . . . ?
N1 C1 C2 C3 -46.3(4) . . . . ?
C9 C1 C2 C3 80.7(3) . . . . ?
C1 C2 C3 C4 55.6(4) . . . . ?
Si1 O1 C4 C3 -134.1(3) . . . . ?
Si1 O1 C4 C5 102.2(3) . . . . ?
C2 C3 C4 O1 178.2(3) . . . . ?
C2 C3 C4 C5 -59.8(3) . . . . ?
C17 N1 C5 C4 131.3(3) . . . . ?
C1 N1 C5 C4 -49.1(3) . . . . ?
C17 N1 C5 C6 -102.6(3) . . . . ?
C1 N1 C5 C6 76.9(3) . . . . ?
O1 C4 C5 N1 177.0(2) . . . . ?
C3 C4 C5 N1 54.7(3) . . . . ?
O1 C4 C5 C6 50.3(4) . . . . ?
C3 C4 C5 C6 -72.0(4) . . . . ?
N1 C5 C6 C7 61.1(4) . . . . ?
C4 C5 C6 C7 -175.3(3) . . . . ?
C5 C6 C7 C8 -132.7(5) . . . . ?
N1 C1 C9 C10 -158.0(2) . . . . ?
C2 C1 C9 C10 76.6(3) . . . . ?
C1 C9 C10 O2 -8.6(5) . . . . ?
C1 C9 C10 C11 171.5(3) . . . . ?
O2 C10 C11 C16 6.2(5) . . . . ?
C9 C10 C11 C16 -173.9(3) . . . . ?
O2 C10 C11 C12 -174.1(4) . . . . ?
C9 C10 C11 C12 5.8(4) . . . . ?
C16 C11 C12 C13 -0.3(5) . . . . ?
C10 C11 C12 C13 180.0(4) . . . . ?
C11 C12 C13 C14 1.0(6) . . . . ?
C12 C13 C14 C15 -1.5(7) . . . . ?
C13 C14 C15 C16 1.4(6) . . . . ?
C14 C15 C16 C11 -0.7(5) . . . . ?
C12 C11 C16 C15 0.2(5) . . . . ?
C10 C11 C16 C15 179.9(3) . . . . ?
C18 O4 C17 O3 -5.3(5) . . . . ?
C18 O4 C17 N1 175.0(3) . . . . ?
C5 N1 C17 O3 173.6(3) . . . . ?
C1 N1 C17 O3 -6.0(4) . . . . ?
C5 N1 C17 O4 -6.7(4) . . . . ?
C1 N1 C17 O4 173.7(2) . . . . ?
C17 O4 C18 C21 62.3(6) . . . . ?
C17 O4 C18 C20 -63.9(6) . . . . ?
C17 O4 C18 C19 -179.9(5) . . . . ?
O1 Si1 C24 C26 175.2(7) . . . . ?
C22 Si1 C24 C26 -65.4(8) . . . . ?
C23 Si1 C24 C26 58.1(8) . . . . ?
O1 Si1 C24 C25 -61.3(4) . . . . ?
C22 Si1 C24 C25 58.1(4) . . . . ?
C23 Si1 C24 C25 -178.5(4) . . . . ?
O1 Si1 C24 C27 55.1(4) . . . . ?
C22 Si1 C24 C27 174.5(4) . . . . ?
C23 Si1 C24 C27 -62.1(4) . . . . ?

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.025

_shelxl_version_number           2013-4

