# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_sarpong62
_database_code_depnum_ccdc_archive 'CCDC 1568998'
_audit_update_record             
;
2017-08-14 deposited with the CCDC.
2017-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 sarpong62 
;
_chemical_name_common            RMXIII-128B1
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H15 N O3'
_chemical_formula_weight         269.29

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'

_diffrn_refln_scan_width         1.0
_diffrn_refln_scan_rate          10
_space_group.centring_type       primitive

_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                   6.3718(4)
_cell_length_b                   11.6995(7)
_cell_length_c                   17.3017(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1289.79(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9987
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      68.24

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.786
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.880
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_reflns_number            15734
_diffrn_reflns_av_unetI/netI     0.0089
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.562
_diffrn_reflns_theta_max         68.230
_diffrn_reflns_theta_full        67.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2352
_reflns_number_gt                2341
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_max     1.000
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXT
_computing_structure_refinement  SHELXL-2013
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX

_refine_special_details          
; 
 Refined as a 2-component inversion 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)+(0.0409P)²+0.4273P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.5(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2352
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0821
_refine_ls_wR_factor_gt          0.0820
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.114
_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 0.9554(3) 0.11845(18) 0.21280(12) 0.0219(4) Uani 1 1 d . . . . .
C2 C 1.1249(4) 0.19488(18) 0.24700(12) 0.0251(5) Uani 1 1 d . . . . .
H2A H 1.2691 0.1866 0.2265 0.030 Uiso 1 1 calc R U . . .
H2B H 1.0851 0.2741 0.2607 0.030 Uiso 1 1 calc R U . . .
C3 C 1.0426(3) 0.10106(18) 0.29675(12) 0.0228(5) Uani 1 1 d . . . . .
C4 C 1.1814(3) 0.00025(18) 0.31115(12) 0.0246(5) Uani 1 1 d . . . . .
C5 C 1.1113(4) -0.07968(18) 0.37107(12) 0.0260(5) Uani 1 1 d . . . . .
H5 H 1.2073 -0.1351 0.3900 0.031 Uiso 1 1 calc R U . . .
C6 C 0.9161(4) -0.07708(18) 0.39997(12) 0.0264(5) Uani 1 1 d . . . . .
C7 C 0.7626(4) 0.01322(19) 0.37571(12) 0.0263(5) Uani 1 1 d . . . . .
H7A H 0.6636 0.0272 0.4188 0.032 Uiso 1 1 calc R U . . .
H7B H 0.6803 -0.0157 0.3313 0.032 Uiso 1 1 calc R U . . .
C8 C 0.8647(4) 0.12643(18) 0.35294(12) 0.0244(5) Uani 1 1 d . . . . .
H8 H 0.9187 0.1673 0.3996 0.029 Uiso 1 1 calc R U . . .
C9 C 0.7117(4) 0.20204(19) 0.30801(12) 0.0264(5) Uani 1 1 d . . . . .
H9A H 0.5655 0.1880 0.3249 0.032 Uiso 1 1 calc R U . . .
H9B H 0.7450 0.2839 0.3157 0.032 Uiso 1 1 calc R U . . .
C10 C 0.7407(3) 0.16820(17) 0.22347(12) 0.0223(4) Uani 1 1 d . . . . .
C11 C 0.9944(3) 0.03733(18) 0.14848(12) 0.0220(4) Uani 1 1 d . . . . .
C12 C 1.1837(3) 0.03191(19) 0.10817(12) 0.0260(5) Uani 1 1 d . . . . .
H12 H 1.2954 0.0820 0.1216 0.031 Uiso 1 1 calc R U . . .
C13 C 1.2096(4) -0.0454(2) 0.04916(12) 0.0295(5) Uani 1 1 d . . . . .
H13 H 1.3401 -0.0488 0.0227 0.035 Uiso 1 1 calc R U . . .
C14 C 0.8687(4) -0.11611(19) 0.06732(13) 0.0292(5) Uani 1 1 d . . . . .
H14 H 0.7602 -0.1679 0.0535 0.035 Uiso 1 1 calc R U . . .
C15 C 0.8381(4) -0.04039(18) 0.12731(12) 0.0247(5) Uani 1 1 d . . . . .
H15 H 0.7089 -0.0410 0.1547 0.030 Uiso 1 1 calc R U . . .
C16 C 0.8353(4) -0.1659(2) 0.45444(13) 0.0348(6) Uani 1 1 d . . . . .
H16A H 0.9398 -0.2267 0.4601 0.052 Uiso 1 1 calc R U . . .
H16B H 0.7046 -0.1982 0.4340 0.052 Uiso 1 1 calc R U . . .
H16C H 0.8083 -0.1310 0.5050 0.052 Uiso 1 1 calc R U . . .
N1 N 1.0527(3) -0.11714(16) 0.02794(10) 0.0305(5) Uani 1 1 d . . . . .
O1 O 1.3393(2) -0.01598(13) 0.27316(9) 0.0291(4) Uani 1 1 d . . . . .
O2 O 0.6125(2) 0.17868(12) 0.17229(8) 0.0256(3) Uani 1 1 d . . . . .
O3 O 1.0760(3) -0.18635(15) -0.03077(10) 0.0438(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C11 1.484(3) . ?
C1 C10 1.498(3) . ?
C1 C2 1.522(3) . ?
C1 C3 1.568(3) . ?
C2 C3 1.490(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.495(3) . ?
C3 C8 1.522(3) . ?
C4 O1 1.217(3) . ?
C4 C5 1.466(3) . ?
C5 C6 1.341(3) . ?
C5 H5 0.9500 . ?
C6 C16 1.494(3) . ?
C6 C7 1.499(3) . ?
C7 C8 1.527(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.529(3) . ?
C8 H8 1.0000 . ?
C9 C10 1.527(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 O2 1.211(3) . ?
C11 C12 1.395(3) . ?
C11 C15 1.397(3) . ?
C12 C13 1.374(3) . ?
C12 H12 0.9500 . ?
C13 N1 1.356(3) . ?
C13 H13 0.9500 . ?
C14 N1 1.356(3) . ?
C14 C15 1.378(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N1 O3 1.307(2) . ?

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
C11 C1 C10 119.61(18) . . ?
C11 C1 C2 123.27(18) . . ?
C10 C1 C2 111.82(17) . . ?
C11 C1 C3 123.52(18) . . ?
C10 C1 C3 105.06(17) . . ?
C2 C1 C3 57.64(13) . . ?
C3 C2 C1 62.75(13) . . ?
C3 C2 H2A 117.5 . . ?
C1 C2 H2A 117.5 . . ?
C3 C2 H2B 117.5 . . ?
C1 C2 H2B 117.5 . . ?
H2A C2 H2B 114.6 . . ?
C2 C3 C4 117.99(19) . . ?
C2 C3 C8 119.15(18) . . ?
C4 C3 C8 119.18(18) . . ?
C2 C3 C1 59.61(13) . . ?
C4 C3 C1 117.79(17) . . ?
C8 C3 C1 107.60(17) . . ?
O1 C4 C5 122.3(2) . . ?
O1 C4 C3 121.5(2) . . ?
C5 C4 C3 116.17(19) . . ?
C6 C5 C4 122.1(2) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C16 122.6(2) . . ?
C5 C6 C7 121.1(2) . . ?
C16 C6 C7 116.2(2) . . ?
C6 C7 C8 113.92(19) . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C3 C8 C7 108.23(17) . . ?
C3 C8 C9 105.24(17) . . ?
C7 C8 C9 111.17(18) . . ?
C3 C8 H8 110.7 . . ?
C7 C8 H8 110.7 . . ?
C9 C8 H8 110.7 . . ?
C10 C9 C8 105.06(17) . . ?
C10 C9 H9A 110.7 . . ?
C8 C9 H9A 110.7 . . ?
C10 C9 H9B 110.7 . . ?
C8 C9 H9B 110.7 . . ?
H9A C9 H9B 108.8 . . ?
O2 C10 C1 124.42(19) . . ?
O2 C10 C9 126.34(19) . . ?
C1 C10 C9 109.24(18) . . ?
C12 C11 C15 117.10(19) . . ?
C12 C11 C1 123.31(19) . . ?
C15 C11 C1 119.57(19) . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
N1 C13 C12 121.3(2) . . ?
N1 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
N1 C14 C15 120.4(2) . . ?
N1 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C11 121.0(2) . . ?
C14 C15 H15 119.5 . . ?
C11 C15 H15 119.5 . . ?
C6 C16 H16A 109.5 . . ?
C6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 N1 C13 120.7(2) . . ?
O3 N1 C14 119.6(2) . . ?
C13 N1 C14 119.73(18) . . ?

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.037

_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_sarpong43
_database_code_depnum_ccdc_archive 'CCDC 1568996'
_audit_update_record             
;
2017-08-14 deposited with the CCDC.
2017-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
; 
 sarpong43 
;
_chemical_name_common            VLI-005B3
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H30 O4 Si'
_chemical_formula_weight         338.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_diffrn_refln_scan_width         0.5
_diffrn_refln_scan_rate          10
_space_group.centring_type       primitive

_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'

_cell_length_a                   6.9205(7)
_cell_length_b                   7.0658(7)
_cell_length_c                   20.0779(19)
_cell_angle_alpha                81.6640(10)
_cell_angle_beta                 80.2810(10)
_cell_angle_gamma                80.8850(10)
_cell_volume                     948.40(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9572
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      25.40

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.140
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.788
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed source'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_reflns_number            22218
_diffrn_reflns_av_unetI/netI     0.0097
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.074
_diffrn_reflns_theta_max         25.401
_diffrn_reflns_theta_full        25.000
_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             3493
_reflns_number_gt                3368
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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    SIR-2011
_computing_structure_refinement  SHELXL-2012
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX

_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)+(0.0368P)²+0.4714P] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3493
_refine_ls_number_parameters     215
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0760
_refine_ls_wR_factor_gt          0.0751
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.19942(16) 0.56948(15) 0.33876(5) 0.0131(2) Uani 1 1 d . . . . .
C2 C 0.02984(16) 0.62189(16) 0.29638(5) 0.0136(2) Uani 1 1 d . . . . .
H2 H -0.0302 0.5029 0.2952 0.016 Uiso 1 1 calc R U . . .
C3 C -0.12794(16) 0.77154(16) 0.32528(6) 0.0151(2) Uani 1 1 d . . . . .
H3 H -0.2514 0.7915 0.3088 0.018 Uiso 1 1 calc R U . . .
C4 C -0.10751(17) 0.87832(16) 0.37227(6) 0.0156(2) Uani 1 1 d . . . . .
C5 C 0.08031(17) 0.85955(16) 0.40264(6) 0.0175(2) Uani 1 1 d . . . . .
H5A H 0.0539 0.8031 0.4508 0.021 Uiso 1 1 calc R U . . .
H5B H 0.1141 0.9908 0.4022 0.021 Uiso 1 1 calc R U . . .
C6 C 0.26197(16) 0.73667(16) 0.36739(6) 0.0150(2) Uani 1 1 d . . . . .
H6 H 0.3398 0.8179 0.3308 0.018 Uiso 1 1 calc R U . . .
C7 C 0.39211(17) 0.63225(17) 0.42103(6) 0.0187(2) Uani 1 1 d . . . . .
H7A H 0.5296 0.5946 0.3993 0.022 Uiso 1 1 calc R U . . .
H7B H 0.3940 0.7162 0.4563 0.022 Uiso 1 1 calc R U . . .
C8 C 0.29304(17) 0.45247(17) 0.45227(6) 0.0187(2) Uani 1 1 d . . . . .
H8A H 0.3931 0.3359 0.4550 0.022 Uiso 1 1 calc R U . . .
H8B H 0.2218 0.4691 0.4986 0.022 Uiso 1 1 calc R U . . .
C9 C 0.14957(16) 0.43489(15) 0.40481(5) 0.0146(2) Uani 1 1 d . . . . .
C10 C 0.37569(16) 0.46371(16) 0.29532(5) 0.0156(2) Uani 1 1 d . . . . .
C11 C 0.47992(19) 0.18330(18) 0.24046(6) 0.0240(3) Uani 1 1 d . . . . .
H11A H 0.5067 0.2586 0.1957 0.036 Uiso 1 1 calc R U . . .
H11B H 0.4330 0.0633 0.2352 0.036 Uiso 1 1 calc R U . . .
H11C H 0.6017 0.1525 0.2610 0.036 Uiso 1 1 calc R U . . .
C12 C -0.02924(19) 0.42363(18) 0.15824(6) 0.0220(3) Uani 1 1 d . . . . .
H12A H 0.0891 0.3306 0.1647 0.033 Uiso 1 1 calc R U . . .
H12B H -0.0705 0.4123 0.1148 0.033 Uiso 1 1 calc R U . . .
H12C H -0.1362 0.3969 0.1955 0.033 Uiso 1 1 calc R U . . .
C13 C -0.20013(17) 0.85013(18) 0.15038(6) 0.0214(3) Uani 1 1 d . . . . .
H13A H -0.3082 0.8100 0.1851 0.032 Uiso 1 1 calc R U . . .
H13B H -0.2373 0.8555 0.1051 0.032 Uiso 1 1 calc R U . . .
H13C H -0.1747 0.9781 0.1571 0.032 Uiso 1 1 calc R U . . .
C14 C 0.23154(17) 0.73612(17) 0.08663(6) 0.0165(2) Uani 1 1 d . . . . .
C15 C 0.16687(19) 0.72647(19) 0.01765(6) 0.0237(3) Uani 1 1 d . . . . .
H15A H 0.0438 0.8145 0.0134 0.036 Uiso 1 1 calc R U . . .
H15B H 0.1451 0.5943 0.0149 0.036 Uiso 1 1 calc R U . . .
H15C H 0.2705 0.7645 -0.0193 0.036 Uiso 1 1 calc R U . . .
C16 C 0.42149(17) 0.59364(18) 0.09303(6) 0.0215(3) Uani 1 1 d . . . . .
H16A H 0.5260 0.6295 0.0561 0.032 Uiso 1 1 calc R U . . .
H16B H 0.3960 0.4627 0.0902 0.032 Uiso 1 1 calc R U . . .
H16C H 0.4637 0.5978 0.1369 0.032 Uiso 1 1 calc R U . . .
C17 C 0.27382(19) 0.94135(18) 0.08963(6) 0.0229(3) Uani 1 1 d . . . . .
H17A H 0.3127 0.9484 0.1338 0.034 Uiso 1 1 calc R U . . .
H17B H 0.1544 1.0334 0.0837 0.034 Uiso 1 1 calc R U . . .
H17C H 0.3813 0.9733 0.0532 0.034 Uiso 1 1 calc R U . . .
C18 C -0.27436(18) 1.02116(17) 0.40130(6) 0.0211(3) Uani 1 1 d . . . . .
H18A H -0.3957 1.0094 0.3840 0.032 Uiso 1 1 calc R U . . .
H18B H -0.2410 1.1524 0.3877 0.032 Uiso 1 1 calc R U . . .
H18C H -0.2950 0.9947 0.4511 0.032 Uiso 1 1 calc R U . . .
O1 O 0.53168(12) 0.52061(13) 0.27438(4) 0.0220(2) Uani 1 1 d . . . . .
O2 O 0.33010(12) 0.29457(12) 0.28395(4) 0.01944(19) Uani 1 1 d . . . . .
O3 O 0.11580(11) 0.68899(11) 0.22824(4) 0.01472(17) Uani 1 1 d . . . . .
O4 O 0.01448(13) 0.34067(12) 0.41749(4) 0.02061(19) Uani 1 1 d . . . . .
Si1 Si 0.02768(4) 0.67292(4) 0.15771(2) 0.01344(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.5319(15) . ?
C1 C10 1.5324(15) . ?
C1 C6 1.5350(15) . ?
C1 C9 1.5381(15) . ?
C2 O3 1.4412(13) . ?
C2 C3 1.4984(15) . ?
C2 H2 1.0000 . ?
C3 C4 1.3284(16) . ?
C3 H3 0.9500 . ?
C4 C18 1.5052(16) . ?
C4 C5 1.5061(16) . ?
C5 C6 1.5385(16) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.5498(15) . ?
C6 H6 1.0000 . ?
C7 C8 1.5417(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5172(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O4 1.2040(14) . ?
C10 O1 1.1996(14) . ?
C10 O2 1.3427(14) . ?
C11 O2 1.4459(14) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 Si1 1.8631(12) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 Si1 1.8640(12) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C17 1.5355(17) . ?
C14 C16 1.5357(16) . ?
C14 C15 1.5394(15) . ?
C14 Si1 1.8873(12) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
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 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O3 Si1 1.6583(8) . ?

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
C2 C1 C10 107.68(9) . . ?
C2 C1 C6 116.38(9) . . ?
C10 C1 C6 110.82(9) . . ?
C2 C1 C9 113.61(9) . . ?
C10 C1 C9 107.51(9) . . ?
C6 C1 C9 100.47(8) . . ?
O3 C2 C3 111.28(9) . . ?
O3 C2 C1 106.90(8) . . ?
C3 C2 C1 112.04(9) . . ?
O3 C2 H2 108.8 . . ?
C3 C2 H2 108.8 . . ?
C1 C2 H2 108.8 . . ?
C4 C3 C2 124.66(10) . . ?
C4 C3 H3 117.7 . . ?
C2 C3 H3 117.7 . . ?
C3 C4 C18 122.17(11) . . ?
C3 C4 C5 122.72(10) . . ?
C18 C4 C5 115.06(10) . . ?
C4 C5 C6 116.22(9) . . ?
C4 C5 H5A 108.2 . . ?
C6 C5 H5A 108.2 . . ?
C4 C5 H5B 108.2 . . ?
C6 C5 H5B 108.2 . . ?
H5A C5 H5B 107.4 . . ?
C1 C6 C5 110.72(9) . . ?
C1 C6 C7 103.23(9) . . ?
C5 C6 C7 109.63(9) . . ?
C1 C6 H6 111.0 . . ?
C5 C6 H6 111.0 . . ?
C7 C6 H6 111.0 . . ?
C8 C7 C6 104.53(9) . . ?
C8 C7 H7A 110.8 . . ?
C6 C7 H7A 110.8 . . ?
C8 C7 H7B 110.8 . . ?
C6 C7 H7B 110.8 . . ?
H7A C7 H7B 108.9 . . ?
C9 C8 C7 105.47(9) . . ?
C9 C8 H8A 110.6 . . ?
C7 C8 H8A 110.6 . . ?
C9 C8 H8B 110.6 . . ?
C7 C8 H8B 110.6 . . ?
H8A C8 H8B 108.8 . . ?
O4 C9 C8 126.50(10) . . ?
O4 C9 C1 125.80(10) . . ?
C8 C9 C1 107.61(9) . . ?
O1 C10 O2 124.37(10) . . ?
O1 C10 C1 126.06(10) . . ?
O2 C10 C1 109.57(9) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
Si1 C12 H12A 109.5 . . ?
Si1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
Si1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Si1 C13 H13A 109.5 . . ?
Si1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
Si1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C17 C14 C16 109.17(10) . . ?
C17 C14 C15 109.37(10) . . ?
C16 C14 C15 108.67(9) . . ?
C17 C14 Si1 109.49(8) . . ?
C16 C14 Si1 110.61(8) . . ?
C15 C14 Si1 109.51(8) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 O2 C11 115.59(9) . . ?
C2 O3 Si1 125.50(7) . . ?
O3 Si1 C12 110.01(5) . . ?
O3 Si1 C13 110.30(5) . . ?
C12 Si1 C13 109.82(6) . . ?
O3 Si1 C14 104.48(5) . . ?
C12 Si1 C14 111.99(5) . . ?
C13 Si1 C14 110.13(5) . . ?

_refine_diff_density_max         0.334
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.041

_shelxl_version_number           2012-9

####################################################################### 
# 
# 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_sarpong59
_database_code_depnum_ccdc_archive 'CCDC 1568997'
_audit_update_record             
;
2017-08-14 deposited with the CCDC.
2017-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 sarpong59 
;
_chemical_name_common            RMXII-193
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H33 N O3 Si'
_chemical_formula_weight         387.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_diffrn_refln_scan_width         1.0
_diffrn_refln_scan_rate          5
_space_group.centring_type       primitive

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

_cell_length_a                   17.6138(8)
_cell_length_b                   11.1045(5)
_cell_length_c                   11.1829(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.906(2)
_cell_angle_gamma                90
_cell_volume                     2182.21(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9656
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      68.25

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.110
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.877
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_reflns_number            32201
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.514
_diffrn_reflns_theta_max         68.247
_diffrn_reflns_theta_full        67.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3982
_reflns_number_gt                3468
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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    SHELXT
_computing_structure_refinement  SHELXL-2013
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX

_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)+(0.0687P)²+2.2930P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3982
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1498
_refine_ls_wR_factor_gt          0.1435
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.34709(11) 0.38234(17) 0.27199(17) 0.0221(4) Uani 1 1 d . . . . .
C2 C 0.40190(11) 0.45961(17) 0.35263(17) 0.0216(4) Uani 1 1 d . . . . .
C3 C 0.44862(11) 0.37761(18) 0.43033(18) 0.0249(4) Uani 1 1 d . . . . .
H3 H 0.4622 0.3987 0.5161 0.030 Uiso 1 1 calc R U . . .
C4 C 0.43067(11) 0.24957(18) 0.39449(18) 0.0249(4) Uani 1 1 d . . . . .
H4A H 0.3956 0.2121 0.4492 0.030 Uiso 1 1 calc R U . . .
H4B H 0.4776 0.2005 0.3941 0.030 Uiso 1 1 calc R U . . .
C5 C 0.39249(11) 0.26284(17) 0.26708(17) 0.0225(4) Uani 1 1 d . . . . .
H5 H 0.4337 0.2753 0.2112 0.027 Uiso 1 1 calc R U . . .
C6 C 0.34595(12) 0.15436(18) 0.22225(19) 0.0275(4) Uani 1 1 d . . . . .
H6A H 0.3404 0.1569 0.1336 0.033 Uiso 1 1 calc R U . . .
H6B H 0.3743 0.0801 0.2457 0.033 Uiso 1 1 calc R U . . .
C7 C 0.26832(12) 0.1476(2) 0.2690(2) 0.0337(5) Uani 1 1 d . . . . .
C8 C 0.23754(12) 0.2418(2) 0.3197(2) 0.0366(5) Uani 1 1 d . . . . .
H8 H 0.1873 0.2325 0.3442 0.044 Uiso 1 1 calc R U . . .
C9 C 0.27488(11) 0.36213(19) 0.34201(19) 0.0272(5) Uani 1 1 d . . . . .
H9 H 0.2936 0.3610 0.4284 0.033 Uiso 1 1 calc R U . A 1
C10 C 0.32705(13) 0.43619(19) 0.14850(18) 0.0297(5) Uani 1 1 d . . . . .
H10A H 0.2947 0.3793 0.0995 0.036 Uiso 1 1 calc R U . . .
H10B H 0.2983 0.5120 0.1565 0.036 Uiso 1 1 calc R U . . .
C11 C 0.38443(10) 0.58635(17) 0.38587(17) 0.0216(4) Uani 1 1 d . . . . .
C12 C 0.34756(12) 0.61651(18) 0.48720(18) 0.0271(4) Uani 1 1 d . . . . .
H12 H 0.3282 0.5554 0.5363 0.033 Uiso 1 1 calc R U . . .
C13 C 0.33922(12) 0.7365(2) 0.51600(19) 0.0303(5) Uani 1 1 d . . . . .
H13 H 0.3132 0.7556 0.5853 0.036 Uiso 1 1 calc R U . . .
C14 C 0.40049(12) 0.79776(19) 0.3542(2) 0.0302(5) Uani 1 1 d . . . . .
H14 H 0.4196 0.8608 0.3072 0.036 Uiso 1 1 calc R U . . .
C15 C 0.41036(11) 0.68063(18) 0.31734(18) 0.0262(4) Uani 1 1 d . . . . .
H15 H 0.4346 0.6644 0.2458 0.031 Uiso 1 1 calc R U . . .
C16 C 0.22808(15) 0.0282(2) 0.2547(3) 0.0552(8) Uani 1 1 d . . . . .
H16A H 0.1779 0.0340 0.2871 0.083 Uiso 1 1 calc R U . . .
H16B H 0.2582 -0.0340 0.2982 0.083 Uiso 1 1 calc R U . . .
H16C H 0.2220 0.0071 0.1695 0.083 Uiso 1 1 calc R U . . .
C17 C 0.1065(3) 0.3902(5) 0.1443(5) 0.0446(13) Uiso 0.643(4) 1 d . . P B 1
H17A H 0.1338 0.4307 0.0822 0.067 Uiso 0.643(4) 1 calc R U P B 1
H17B H 0.0516 0.3963 0.1247 0.067 Uiso 0.643(4) 1 calc R U P B 1
H17C H 0.1214 0.3052 0.1484 0.067 Uiso 0.643(4) 1 calc R U P B 1
C18 C 0.0738(3) 0.3971(4) 0.4115(4) 0.0468(10) Uiso 0.643(4) 1 d . . P B 1
H18A H 0.0792 0.3093 0.4103 0.070 Uiso 0.643(4) 1 calc R U P B 1
H18B H 0.0201 0.4187 0.3950 0.070 Uiso 0.643(4) 1 calc R U P B 1
H18C H 0.0918 0.4279 0.4906 0.070 Uiso 0.643(4) 1 calc R U P B 1
C19 C 0.1128(2) 0.6314(3) 0.2846(3) 0.0356(9) Uiso 0.643(4) 1 d . . P B 1
C20 C 0.0332(3) 0.6543(5) 0.2248(5) 0.0602(13) Uiso 0.643(4) 1 d . . P B 1
H20A H 0.0242 0.7412 0.2185 0.090 Uiso 0.643(4) 1 calc R U P B 1
H20B H -0.0051 0.6178 0.2732 0.090 Uiso 0.643(4) 1 calc R U P B 1
H20C H 0.0295 0.6185 0.1445 0.090 Uiso 0.643(4) 1 calc R U P B 1
C21 C 0.1724(2) 0.6935(4) 0.2125(4) 0.0429(10) Uiso 0.643(4) 1 d . . P B 1
H21A H 0.1740 0.6545 0.1342 0.064 Uiso 0.643(4) 1 calc R U P B 1
H21B H 0.2225 0.6873 0.2560 0.064 Uiso 0.643(4) 1 calc R U P B 1
H21C H 0.1590 0.7786 0.2013 0.064 Uiso 0.643(4) 1 calc R U P B 1
C22 C 0.1174(3) 0.6865(5) 0.4104(4) 0.0502(11) Uiso 0.643(4) 1 d . . P B 1
H22A H 0.1085 0.7734 0.4045 0.075 Uiso 0.643(4) 1 calc R U P B 1
H22B H 0.1680 0.6715 0.4496 0.075 Uiso 0.643(4) 1 calc R U P B 1
H22C H 0.0787 0.6497 0.4577 0.075 Uiso 0.643(4) 1 calc R U P B 1
C17A C 0.1503(8) 0.6708(12) 0.3950(12) 0.086(4) Uiso 0.357(4) 1 d . . P B 2
H17D H 0.1759 0.6683 0.4756 0.128 Uiso 0.357(4) 1 calc R U P B 2
H17E H 0.0995 0.7057 0.3990 0.128 Uiso 0.357(4) 1 calc R U P B 2
H17F H 0.1801 0.7203 0.3428 0.128 Uiso 0.357(4) 1 calc R U P B 2
C18A C 0.1002(5) 0.4121(8) 0.4523(8) 0.050(2) Uiso 0.357(4) 1 d . . P B 2
H18D H 0.0797 0.3388 0.4136 0.075 Uiso 0.357(4) 1 calc R U P B 2
H18E H 0.0594 0.4548 0.4901 0.075 Uiso 0.357(4) 1 calc R U P B 2
H18F H 0.1404 0.3906 0.5135 0.075 Uiso 0.357(4) 1 calc R U P B 2
C19A C 0.0768(5) 0.5088(8) 0.1905(7) 0.050(2) Uiso 0.357(4) 1 d . . P B 2
C20A C -0.0050(6) 0.5366(9) 0.2179(9) 0.066(3) Uiso 0.357(4) 1 d . . P B 2
H20D H -0.0364 0.5453 0.1426 0.099 Uiso 0.357(4) 1 calc R U P B 2
H20E H -0.0062 0.6118 0.2636 0.099 Uiso 0.357(4) 1 calc R U P B 2
H20F H -0.0248 0.4707 0.2650 0.099 Uiso 0.357(4) 1 calc R U P B 2
C21A C 0.1041(7) 0.6114(11) 0.1090(11) 0.083(3) Uiso 0.357(4) 1 d . . P B 2
H21D H 0.1556 0.5934 0.0860 0.125 Uiso 0.357(4) 1 calc R U P B 2
H21E H 0.1045 0.6878 0.1528 0.125 Uiso 0.357(4) 1 calc R U P B 2
H21F H 0.0695 0.6175 0.0368 0.125 Uiso 0.357(4) 1 calc R U P B 2
C22A C 0.0844(8) 0.3953(14) 0.1305(14) 0.082(4) Uiso 0.357(4) 1 d . . P B 2
H22D H 0.0535 0.3961 0.0543 0.122 Uiso 0.357(4) 1 calc R U P B 2
H22E H 0.0670 0.3302 0.1812 0.122 Uiso 0.357(4) 1 calc R U P B 2
H22F H 0.1379 0.3822 0.1152 0.122 Uiso 0.357(4) 1 calc R U P B 2
N1 N 0.36548(10) 0.82749(15) 0.45232(16) 0.0301(4) Uani 1 1 d . . . . .
O1 O 0.39500(10) 0.45928(14) 0.09191(14) 0.0382(4) Uani 1 1 d . . . . .
H1 H 0.3877 0.5157 0.0424 0.057 Uiso 1 1 calc R U . . .
O2 O 0.48208(8) 0.44312(13) 0.33402(13) 0.0264(3) Uani 1 1 d . . . . .
O3 O 0.2250(5) 0.4558(8) 0.3316(6) 0.0238(11) Uani 0.643(4) 1 d . . P B 1
O3A O 0.2220(11) 0.4700(17) 0.2971(12) 0.039(3) Uani 0.357(4) 1 d . . P B 2
Si1 Si 0.13140(6) 0.46469(15) 0.29475(13) 0.0259(4) Uani 0.643(4) 1 d . . P B 1
Si1A Si 0.14184(13) 0.5151(3) 0.3335(3) 0.0432(7) Uani 0.357(4) 1 d . . P B 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
C1 C10 1.524(3) . ?
C1 C2 1.537(3) . ?
C1 C5 1.552(3) . ?
C1 C9 1.555(3) . ?
C2 O2 1.453(2) . ?
C2 C3 1.471(3) . ?
C2 C11 1.493(3) . ?
C3 O2 1.457(2) . ?
C3 C4 1.505(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.541(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.523(3) . ?
C5 H5 1.0000 . ?
C6 C7 1.499(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.324(3) . ?
C7 C16 1.506(3) . ?
C8 C9 1.503(3) . ?
C8 H8 0.9500 . ?
C9 O3 1.361(9) . ?
C9 O3A 1.579(16) . ?
C9 H9 1.0000 . ?
C10 O1 1.415(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.385(3) . ?
C11 C15 1.393(3) . ?
C12 C13 1.381(3) . ?
C12 H12 0.9500 . ?
C13 N1 1.337(3) . ?
C13 H13 0.9500 . ?
C14 N1 1.336(3) . ?
C14 C15 1.379(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 Si1 1.899(6) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 Si1 1.865(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C21 1.531(5) . ?
C19 C22 1.532(6) . ?
C19 C20 1.533(6) . ?
C19 Si1 1.882(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C17A Si1A 1.864(14) . ?
C17A H17D 0.9800 . ?
C17A H17E 0.9800 . ?
C17A H17F 0.9800 . ?
C18A Si1A 1.935(9) . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?
C19A C22A 1.438(17) . ?
C19A C20A 1.524(12) . ?
C19A C21A 1.556(14) . ?
C19A Si1A 1.904(9) . ?
C20A H20D 0.9800 . ?
C20A H20E 0.9800 . ?
C20A H20F 0.9800 . ?
C21A H21D 0.9800 . ?
C21A H21E 0.9800 . ?
C21A H21F 0.9800 . ?
C22A H22D 0.9800 . ?
C22A H22E 0.9800 . ?
C22A H22F 0.9800 . ?
O1 H1 0.8400 . ?
O3 Si1 1.675(8) . ?
O3A Si1A 1.58(2) . ?

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
C10 C1 C2 114.20(16) . . ?
C10 C1 C5 113.04(16) . . ?
C2 C1 C5 101.15(15) . . ?
C10 C1 C9 111.48(17) . . ?
C2 C1 C9 106.72(15) . . ?
C5 C1 C9 109.61(15) . . ?
O2 C2 C3 59.77(12) . . ?
O2 C2 C11 111.92(15) . . ?
C3 C2 C11 123.57(17) . . ?
O2 C2 C1 115.05(15) . . ?
C3 C2 C1 107.74(16) . . ?
C11 C2 C1 122.71(16) . . ?
O2 C3 C2 59.50(12) . . ?
O2 C3 C4 111.29(16) . . ?
C2 C3 C4 109.18(16) . . ?
O2 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C3 C4 C5 103.09(15) . . ?
C3 C4 H4A 111.1 . . ?
C5 C4 H4A 111.1 . . ?
C3 C4 H4B 111.1 . . ?
C5 C4 H4B 111.1 . . ?
H4A C4 H4B 109.1 . . ?
C6 C5 C4 114.84(16) . . ?
C6 C5 C1 114.88(16) . . ?
C4 C5 C1 104.03(15) . . ?
C6 C5 H5 107.6 . . ?
C4 C5 H5 107.6 . . ?
C1 C5 H5 107.6 . . ?
C7 C6 C5 114.12(17) . . ?
C7 C6 H6A 108.7 . . ?
C5 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C8 C7 C6 121.3(2) . . ?
C8 C7 C16 122.5(2) . . ?
C6 C7 C16 116.2(2) . . ?
C7 C8 C9 125.9(2) . . ?
C7 C8 H8 117.0 . . ?
C9 C8 H8 117.0 . . ?
O3 C9 C8 113.1(4) . . ?
O3 C9 C1 113.1(4) . . ?
C8 C9 C1 114.11(17) . . ?
C8 C9 O3A 112.3(7) . . ?
C1 C9 O3A 102.4(7) . . ?
O3 C9 H9 105.1 . . ?
C8 C9 H9 105.1 . . ?
C1 C9 H9 105.1 . . ?
O1 C10 C1 109.01(17) . . ?
O1 C10 H10A 109.9 . . ?
C1 C10 H10A 109.9 . . ?
O1 C10 H10B 109.9 . . ?
C1 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C12 C11 C15 117.26(18) . . ?
C12 C11 C2 123.21(18) . . ?
C15 C11 C2 119.39(17) . . ?
C13 C12 C11 119.16(19) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
N1 C13 C12 123.98(19) . . ?
N1 C13 H13 118.0 . . ?
C12 C13 H13 118.0 . . ?
N1 C14 C15 123.6(2) . . ?
N1 C14 H14 118.2 . . ?
C15 C14 H14 118.2 . . ?
C14 C15 C11 119.47(19) . . ?
C14 C15 H15 120.3 . . ?
C11 C15 H15 120.3 . . ?
C7 C16 H16A 109.5 . . ?
C7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C7 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Si1 C17 H17A 109.5 . . ?
Si1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
Si1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
Si1 C18 H18A 109.5 . . ?
Si1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
Si1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 C19 C22 107.9(3) . . ?
C21 C19 C20 109.6(3) . . ?
C22 C19 C20 108.9(4) . . ?
C21 C19 Si1 110.6(3) . . ?
C22 C19 Si1 109.8(3) . . ?
C20 C19 Si1 109.9(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
Si1A C17A H17D 109.5 . . ?
Si1A C17A H17E 109.5 . . ?
H17D C17A H17E 109.5 . . ?
Si1A C17A H17F 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
Si1A C18A H18D 109.5 . . ?
Si1A C18A H18E 109.5 . . ?
H18D C18A H18E 109.5 . . ?
Si1A C18A H18F 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
C22A C19A C20A 113.0(9) . . ?
C22A C19A C21A 109.0(9) . . ?
C20A C19A C21A 107.7(8) . . ?
C22A C19A Si1A 110.7(8) . . ?
C20A C19A Si1A 110.3(6) . . ?
C21A C19A Si1A 105.8(6) . . ?
C19A C20A H20D 109.5 . . ?
C19A C20A H20E 109.5 . . ?
H20D C20A H20E 109.5 . . ?
C19A C20A H20F 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
C19A C21A H21D 109.5 . . ?
C19A C21A H21E 109.5 . . ?
H21D C21A H21E 109.5 . . ?
C19A C21A H21F 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?
C19A C22A H22D 109.5 . . ?
C19A C22A H22E 109.5 . . ?
H22D C22A H22E 109.5 . . ?
C19A C22A H22F 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
C14 N1 C13 116.53(18) . . ?
C10 O1 H1 109.5 . . ?
C2 O2 C3 60.73(12) . . ?
C9 O3 Si1 133.2(6) . . ?
Si1A O3A C9 132.7(10) . . ?
O3 Si1 C18 112.2(3) . . ?
O3 Si1 C19 103.7(3) . . ?
C18 Si1 C19 109.70(19) . . ?
O3 Si1 C17 110.9(3) . . ?
C18 Si1 C17 110.0(2) . . ?
C19 Si1 C17 110.3(2) . . ?
O3A Si1A C17A 109.8(8) . . ?
O3A Si1A C19A 105.7(6) . . ?
C17A Si1A C19A 111.9(5) . . ?
O3A Si1A C18A 112.2(6) . . ?
C17A Si1A C18A 108.6(5) . . ?
C19A Si1A C18A 108.7(4) . . ?

_refine_diff_density_max         0.429
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4

