# 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_cx-20180320
_database_code_depnum_ccdc_archive 'CCDC 1835497'
_audit_update_record             
;
2018-04-08 deposited with the CCDC.
2018-09-12 downloaded from the CCDC.
;
_audit_creation_date             2018-03-20
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.02.02 svn.r3481 for OlexSys, GUI svn.r5480)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H28 N4 O Si'
_chemical_formula_sum            'C24 H28 N4 O Si'
_chemical_formula_weight         416.59
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 O1 Si1 N1'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   11.4816(8)
_cell_length_b                   12.2451(6)
_cell_length_c                   16.6439(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2340.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2418
_cell_measurement_temperature    292.64(10)
_cell_measurement_theta_max      25.1920
_cell_measurement_theta_min      3.7720
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.959
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6796
_diffrn_reflns_point_group_measured_fraction_full 0.735
_diffrn_reflns_point_group_measured_fraction_max 0.735
_diffrn_reflns_theta_full        24.979
_diffrn_reflns_theta_max         24.979
_diffrn_reflns_theta_min         3.451
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.64(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):
  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  85.00   1.00   12.00    --   15.98   0.00-180.00  138
  2  ω     35.00  64.00   1.00   12.00    --   15.98  77.00  60.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0411726000
_diffrn_orient_matrix_UB_12      -0.0098049000
_diffrn_orient_matrix_UB_13      0.0309371000
_diffrn_orient_matrix_UB_21      0.0326444000
_diffrn_orient_matrix_UB_22      0.0335926000
_diffrn_orient_matrix_UB_23      0.0264300000
_diffrn_orient_matrix_UB_31      -0.0325245000
_diffrn_orient_matrix_UB_32      0.0461560000
_diffrn_orient_matrix_UB_33      -0.0126338000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.420
_reflns_Friedel_fraction_full    0.452
_reflns_Friedel_fraction_max     0.452
_reflns_number_gt                2441
_reflns_number_total             3019
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Flack x determined using 622 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3019
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0451P)²+0.1166P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0911
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C4(H4), C21(H21), C3(H3), C2(H2), C25(H25), C22(H22),
 C24(H24), C6(H6), C7(H7), C23(H23)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C17(H17A,H17B,H17C), C15(H15A,H15B,H15C), C19(H19A,H19B,
 H19C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Si13 Si 0.19151(10) 0.85465(7) 0.67235(6) 0.0546(3) Uani 1 1 d . . . . .
N30 N 0.3227(2) 0.6192(2) 0.48801(17) 0.0476(7) Uani 1 1 d . . . . .
O12 O 0.2531(2) 0.8176(2) 0.58666(16) 0.0631(7) Uani 1 1 d . . . . .
N29 N 0.2220(2) 0.6638(2) 0.50879(17) 0.0483(7) Uani 1 1 d . . . . .
C26 C 0.3013(3) 0.5138(2) 0.49711(19) 0.0467(8) Uani 1 1 d . . . . .
N27 N 0.1912(3) 0.4957(2) 0.5226(2) 0.0690(9) Uani 1 1 d . . . . .
C20 C 0.3848(3) 0.4272(3) 0.4805(2) 0.0491(8) Uani 1 1 d . . . . .
N28 N 0.1430(3) 0.5925(2) 0.5307(2) 0.0670(9) Uani 1 1 d . . . . .
C1 C 0.2508(3) 0.8415(3) 0.4439(2) 0.0494(9) Uani 1 1 d . . . . .
C9 C 0.0854(4) 0.7782(3) 0.3570(2) 0.0551(9) Uani 1 1 d . . . . .
H9 H 0.052300 0.740232 0.399651 0.066 Uiso 1 1 calc R . . . .
C11 C 0.2018(3) 0.7830(2) 0.5160(2) 0.0513(8) Uani 1 1 d . . . . .
H11 H 0.117834 0.796619 0.518897 0.062 Uiso 1 1 calc R . . . .
C10 C 0.1902(3) 0.8362(3) 0.3690(2) 0.0502(9) Uani 1 1 d . . . . .
C8 C 0.0322(4) 0.7768(3) 0.2842(3) 0.0695(11) Uani 1 1 d . . . . .
H8 H -0.036939 0.738190 0.277744 0.083 Uiso 1 1 calc R . . . .
C5 C 0.2366(4) 0.8953(3) 0.3026(3) 0.0586(10) Uani 1 1 d . . . . .
C4 C 0.3385(4) 0.9568(3) 0.3123(3) 0.0762(14) Uani 1 1 d . . . . .
H4 H 0.368248 0.996125 0.269091 0.091 Uiso 1 1 calc R . . . .
C21 C 0.3620(4) 0.3208(3) 0.5017(2) 0.0680(11) Uani 1 1 d . . . . .
H21 H 0.292209 0.303309 0.526913 0.082 Uiso 1 1 calc R . . . .
C3 C 0.3940(4) 0.9596(3) 0.3838(3) 0.0768(13) Uani 1 1 d . . . . .
H3 H 0.462008 1.000186 0.389272 0.092 Uiso 1 1 calc R . . . .
C2 C 0.3497(4) 0.9012(3) 0.4505(3) 0.0645(10) Uani 1 1 d . . . . .
H2 H 0.388858 0.903821 0.499374 0.077 Uiso 1 1 calc R . . . .
C25 C 0.4895(4) 0.4501(3) 0.4430(3) 0.0688(11) Uani 1 1 d . . . . .
H25 H 0.506630 0.521656 0.428614 0.083 Uiso 1 1 calc R . . . .
C22 C 0.4424(5) 0.2399(3) 0.4857(3) 0.0876(15) Uani 1 1 d . . . . .
H22 H 0.426572 0.168288 0.500826 0.105 Uiso 1 1 calc R . . . .
C18 C 0.0326(3) 0.8725(4) 0.6584(3) 0.0843(13) Uani 1 1 d . . . . .
H18A H 0.018653 0.927569 0.618542 0.127 Uiso 1 1 calc GR . . . .
H18B H -0.002097 0.894418 0.708385 0.127 Uiso 1 1 calc GR . . . .
H18C H -0.001190 0.804703 0.641194 0.127 Uiso 1 1 calc GR . . . .
C24 C 0.5683(4) 0.3695(3) 0.4268(3) 0.0852(14) Uani 1 1 d . . . . .
H24 H 0.638194 0.386388 0.401499 0.102 Uiso 1 1 calc R . . . .
C6 C 0.1784(5) 0.8898(4) 0.2285(3) 0.0762(13) Uani 1 1 d . . . . .
H6 H 0.209101 0.926898 0.184516 0.091 Uiso 1 1 calc R . . . .
C7 C 0.0794(5) 0.8322(3) 0.2194(3) 0.0801(13) Uani 1 1 d . . . . .
H7 H 0.042681 0.829696 0.169677 0.096 Uiso 1 1 calc R . . . .
C23 C 0.5443(5) 0.2635(3) 0.4479(3) 0.0867(14) Uani 1 1 d . . . . .
H23 H 0.597377 0.208290 0.436511 0.104 Uiso 1 1 calc R . . . .
C14 C 0.2645(4) 0.9857(3) 0.6991(2) 0.0656(11) Uani 1 1 d . . . . .
C17 C 0.2321(5) 1.0726(3) 0.6384(3) 0.0962(16) Uani 1 1 d . . . . .
H17A H 0.249611 1.047056 0.585255 0.144 Uiso 1 1 calc GR . . . .
H17B H 0.275688 1.137924 0.649120 0.144 Uiso 1 1 calc GR . . . .
H17C H 0.150294 1.088094 0.642405 0.144 Uiso 1 1 calc GR . . . .
C15 C 0.2265(5) 1.0223(4) 0.7836(3) 0.1037(18) Uani 1 1 d . . . . .
H15A H 0.143699 1.033441 0.784313 0.155 Uiso 1 1 calc GR . . . .
H15B H 0.265109 1.089317 0.797238 0.155 Uiso 1 1 calc GR . . . .
H15C H 0.246836 0.966984 0.821983 0.155 Uiso 1 1 calc GR . . . .
C19 C 0.2210(6) 0.7463(4) 0.7459(3) 0.122(2) Uani 1 1 d . . . . .
H19A H 0.194756 0.677558 0.724973 0.182 Uiso 1 1 calc GR . . . .
H19B H 0.180447 0.762065 0.795035 0.182 Uiso 1 1 calc GR . . . .
H19C H 0.303160 0.742754 0.756257 0.182 Uiso 1 1 calc GR . . . .
C16 C 0.3978(4) 0.9689(4) 0.6988(3) 0.1039(18) Uani 1 1 d . . . . .
H16A H 0.418046 0.912707 0.736538 0.156 Uiso 1 1 calc GR . . . .
H16B H 0.435617 1.035832 0.713754 0.156 Uiso 1 1 calc GR . . . .
H16C H 0.422723 0.947725 0.645999 0.156 Uiso 1 1 calc GR . . . .


_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
Si13 O12 1.655(3) . ?
Si13 C18 1.852(4) . ?
Si13 C14 1.864(4) . ?
Si13 C19 1.837(5) . ?
N30 N29 1.324(4) . ?
N30 C26 1.323(4) . ?
O12 C11 1.381(4) . ?
N29 N28 1.311(4) . ?
N29 C11 1.483(4) . ?
C26 N27 1.351(4) . ?
C26 C20 1.456(5) . ?
N27 N28 1.315(4) . ?
C20 C21 1.375(4) . ?
C20 C25 1.383(5) . ?
C1 C11 1.507(5) . ?
C1 C10 1.429(5) . ?
C1 C2 1.355(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.411(5) . ?
C9 C8 1.357(5) . ?
C11 H11 0.9800 . ?
C10 C5 1.424(5) . ?
C8 H8 0.9300 . ?
C8 C7 1.384(6) . ?
C5 C4 1.401(6) . ?
C5 C6 1.405(6) . ?
C4 H4 0.9300 . ?
C4 C3 1.350(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.380(6) . ?
C3 H3 0.9300 . ?
C3 C2 1.415(6) . ?
C2 H2 0.9300 . ?
C25 H25 0.9300 . ?
C25 C24 1.365(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.359(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C24 H24 0.9300 . ?
C24 C23 1.372(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.347(6) . ?
C7 H7 0.9300 . ?
C23 H23 0.9300 . ?
C14 C17 1.514(6) . ?
C14 C15 1.540(5) . ?
C14 C16 1.544(6) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
O12 Si13 C18 110.20(19) . . ?
O12 Si13 C14 104.46(16) . . ?
O12 Si13 C19 107.3(2) . . ?
C18 Si13 C14 111.8(2) . . ?
C19 Si13 C18 110.5(3) . . ?
C19 Si13 C14 112.3(3) . . ?
C26 N30 N29 102.2(3) . . ?
C11 O12 Si13 129.5(2) . . ?
N30 N29 C11 124.3(3) . . ?
N28 N29 N30 113.7(2) . . ?
N28 N29 C11 121.7(3) . . ?
N30 C26 N27 111.7(3) . . ?
N30 C26 C20 124.5(3) . . ?
N27 C26 C20 123.8(3) . . ?
N28 N27 C26 106.2(3) . . ?
C21 C20 C26 121.1(3) . . ?
C21 C20 C25 118.2(3) . . ?
C25 C20 C26 120.7(3) . . ?
N29 N28 N27 106.3(3) . . ?
C10 C1 C11 119.5(3) . . ?
C2 C1 C11 120.3(4) . . ?
C2 C1 C10 120.2(4) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 121.1(4) . . ?
O12 C11 N29 107.7(3) . . ?
O12 C11 C1 112.0(3) . . ?
O12 C11 H11 109.0 . . ?
N29 C11 C1 110.2(3) . . ?
N29 C11 H11 109.0 . . ?
C1 C11 H11 109.0 . . ?
C9 C10 C1 124.1(3) . . ?
C9 C10 C5 117.7(4) . . ?
C5 C10 C1 118.1(4) . . ?
C9 C8 H8 119.6 . . ?
C9 C8 C7 120.8(4) . . ?
C7 C8 H8 119.6 . . ?
C4 C5 C10 119.8(4) . . ?
C4 C5 C6 121.6(4) . . ?
C6 C5 C10 118.6(4) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.6(4) . . ?
C3 C4 H4 119.7 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.3(4) . . ?
C22 C21 H21 119.9 . . ?
C4 C3 H3 119.7 . . ?
C4 C3 C2 120.6(4) . . ?
C2 C3 H3 119.7 . . ?
C1 C2 C3 120.7(4) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C20 C25 H25 119.4 . . ?
C24 C25 C20 121.2(3) . . ?
C24 C25 H25 119.4 . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.8(4) . . ?
C23 C22 H22 119.6 . . ?
Si13 C18 H18A 109.5 . . ?
Si13 C18 H18B 109.5 . . ?
Si13 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C25 C24 H24 120.0 . . ?
C25 C24 C23 120.0(4) . . ?
C23 C24 H24 120.0 . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.6(4) . . ?
C7 C6 H6 119.2 . . ?
C8 C7 H7 120.0 . . ?
C6 C7 C8 120.1(4) . . ?
C6 C7 H7 120.0 . . ?
C22 C23 C24 119.5(4) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C17 C14 Si13 109.6(3) . . ?
C17 C14 C15 109.6(4) . . ?
C17 C14 C16 109.6(4) . . ?
C15 C14 Si13 109.9(3) . . ?
C15 C14 C16 108.8(4) . . ?
C16 C14 Si13 109.3(3) . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Si13 C19 H19A 109.5 . . ?
Si13 C19 H19B 109.5 . . ?
Si13 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
Si13 O12 C11 N29 -106.9(3) . . . . ?
Si13 O12 C11 C1 131.8(3) . . . . ?
N30 N29 N28 N27 -1.4(4) . . . . ?
N30 N29 C11 O12 -75.7(4) . . . . ?
N30 N29 C11 C1 46.7(4) . . . . ?
N30 C26 N27 N28 -0.8(4) . . . . ?
N30 C26 C20 C21 171.0(3) . . . . ?
N30 C26 C20 C25 -8.9(5) . . . . ?
O12 Si13 C14 C17 66.7(3) . . . . ?
O12 Si13 C14 C15 -172.8(3) . . . . ?
O12 Si13 C14 C16 -53.4(3) . . . . ?
N29 N30 C26 N27 -0.1(4) . . . . ?
N29 N30 C26 C20 179.0(3) . . . . ?
C26 N30 N29 N28 0.9(4) . . . . ?
C26 N30 N29 C11 174.4(3) . . . . ?
C26 N27 N28 N29 1.3(4) . . . . ?
C26 C20 C21 C22 -179.9(4) . . . . ?
C26 C20 C25 C24 -179.7(4) . . . . ?
N27 C26 C20 C21 -10.0(5) . . . . ?
N27 C26 C20 C25 170.0(3) . . . . ?
C20 C26 N27 N28 -179.8(3) . . . . ?
C20 C21 C22 C23 -0.8(7) . . . . ?
C20 C25 C24 C23 -0.1(7) . . . . ?
N28 N29 C11 O12 97.3(4) . . . . ?
N28 N29 C11 C1 -140.3(3) . . . . ?
C1 C10 C5 C4 -0.4(5) . . . . ?
C1 C10 C5 C6 179.4(3) . . . . ?
C9 C10 C5 C4 178.1(3) . . . . ?
C9 C10 C5 C6 -2.2(5) . . . . ?
C9 C8 C7 C6 -1.0(6) . . . . ?
C11 N29 N28 N27 -175.1(3) . . . . ?
C11 C1 C10 C9 -0.4(5) . . . . ?
C11 C1 C10 C5 177.9(3) . . . . ?
C11 C1 C2 C3 -177.7(3) . . . . ?
C10 C1 C11 O12 -165.0(3) . . . . ?
C10 C1 C11 N29 75.2(4) . . . . ?
C10 C1 C2 C3 0.4(5) . . . . ?
C10 C9 C8 C7 0.2(5) . . . . ?
C10 C5 C4 C3 0.8(6) . . . . ?
C10 C5 C6 C7 1.4(6) . . . . ?
C8 C9 C10 C1 179.8(3) . . . . ?
C8 C9 C10 C5 1.4(5) . . . . ?
C5 C4 C3 C2 -0.6(6) . . . . ?
C5 C6 C7 C8 0.2(6) . . . . ?
C4 C5 C6 C7 -178.8(4) . . . . ?
C4 C3 C2 C1 0.0(6) . . . . ?
C21 C20 C25 C24 0.4(6) . . . . ?
C21 C22 C23 C24 1.1(8) . . . . ?
C2 C1 C11 O12 13.1(4) . . . . ?
C2 C1 C11 N29 -106.7(3) . . . . ?
C2 C1 C10 C9 -178.5(3) . . . . ?
C2 C1 C10 C5 -0.2(5) . . . . ?
C25 C20 C21 C22 0.1(6) . . . . ?
C25 C24 C23 C22 -0.6(8) . . . . ?
C18 Si13 O12 C11 -11.7(4) . . . . ?
C18 Si13 C14 C17 -52.4(4) . . . . ?
C18 Si13 C14 C15 68.1(4) . . . . ?
C18 Si13 C14 C16 -172.6(3) . . . . ?
C6 C5 C4 C3 -179.0(4) . . . . ?
C14 Si13 O12 C11 -131.9(3) . . . . ?
C19 Si13 O12 C11 108.7(4) . . . . ?
C19 Si13 C14 C17 -177.3(3) . . . . ?
C19 Si13 C14 C15 -56.8(4) . . . . ?
C19 Si13 C14 C16 62.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.420
_oxdiff_exptl_absorpt_empirical_full_min 0.626
####################################################################### 
# 
# 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_cyg-20180315
_database_code_depnum_ccdc_archive 'CCDC 1835498'
_audit_update_record             
;
2018-04-08 deposited with the CCDC.
2018-09-12 downloaded from the CCDC.
;
_audit_creation_date             2018-03-15
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.02.02 svn.r3481 for OlexSys, GUI svn.r5479)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H24 N4 O Si'
_chemical_formula_sum            'C15 H24 N4 O Si'
_chemical_formula_weight         304.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 N1 O1 Si1'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5430(8)
_cell_length_b                   10.2385(13)
_cell_length_c                   14.1084(19)
_cell_angle_alpha                71.826(12)
_cell_angle_beta                 83.376(10)
_cell_angle_gamma                78.570(10)
_cell_volume                     878.7(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1988
_cell_measurement_temperature    293.0(2)
_cell_measurement_theta_max      25.3180
_cell_measurement_theta_min      4.0640
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.934
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6596
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.448
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):
  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  55.00   1.00   13.00    --   15.98 -99.00 -90.00   75
  2  ω     -1.00  83.00   1.00   13.00    --   15.98  57.00   0.00   84
  3  ω     -1.00  83.00   1.00   13.00    --   15.98  57.00  90.00   84
  4  ω    -11.00  84.00   1.00   13.00    --   15.98  77.00-180.00   95
  5  ω    -53.00  35.00   1.00   13.00    --   15.98 -38.00-180.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0462909000
_diffrn_orient_matrix_UB_12      -0.0652410000
_diffrn_orient_matrix_UB_13      -0.0071766000
_diffrn_orient_matrix_UB_21      0.0252584000
_diffrn_orient_matrix_UB_22      -0.0260662000
_diffrn_orient_matrix_UB_23      0.0508205000
_diffrn_orient_matrix_UB_31      -0.0974259000
_diffrn_orient_matrix_UB_32      -0.0232928000
_diffrn_orient_matrix_UB_33      0.0132304000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2130
_reflns_number_total             3077
_reflns_odcompleteness_completeness 98.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3077
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0675
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0747P)²+0.1072P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1548
_refine_ls_wR_factor_ref         0.1727
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C5(H5)
2.c Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c), C20(H20a,H20b,H20c), C18(H18a,H18b,H18c), C19(H19a,H19b,
 H19c), C16(H16a,H16b,H16c), C17(H17a,H17b,H17c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Si14 Si 0.82746(12) 0.49467(9) 0.26031(7) 0.0546(3) Uani 1 1 d . . . . .
O13 O 0.6551(3) 0.4079(2) 0.33646(14) 0.0555(6) Uani 1 1 d . . . . .
N11 N 0.5305(3) 0.2021(2) 0.41189(17) 0.0452(6) Uani 1 1 d . . . . .
N8 N 0.3324(4) 0.0805(3) 0.3755(2) 0.0636(8) Uani 1 1 d . . . . .
N10 N 0.3494(4) 0.2141(3) 0.46840(19) 0.0617(8) Uani 1 1 d . . . . .
C7 C 0.5167(4) 0.1201(3) 0.3560(2) 0.0449(7) Uani 1 1 d . . . . .
N9 N 0.2347(4) 0.1400(3) 0.4463(2) 0.0718(9) Uani 1 1 d . . . . .
C1 C 0.6739(4) 0.0863(3) 0.2799(2) 0.0447(7) Uani 1 1 d . . . . .
C12 C 0.6954(4) 0.2812(3) 0.4122(2) 0.0479(7) Uani 1 1 d . . . . .
H12 H 0.830696 0.229250 0.396153 0.057 Uiso 1 1 calc R . . . .
C2 C 0.8769(4) 0.0219(3) 0.3047(2) 0.0522(8) Uani 1 1 d . . . . .
H2 H 0.915607 -0.001841 0.370083 0.063 Uiso 1 1 calc R . . . .
C3 C 1.0198(5) -0.0063(3) 0.2308(3) 0.0600(9) Uani 1 1 d . . . . .
H3 H 1.155236 -0.050302 0.246937 0.072 Uiso 1 1 calc R . . . .
C15 C 0.6667(5) 0.6265(3) 0.1616(2) 0.0617(9) Uani 1 1 d . . . . .
C4 C 0.9657(6) 0.0294(4) 0.1343(3) 0.0700(10) Uani 1 1 d . . . . .
H4 H 1.064379 0.010733 0.085101 0.084 Uiso 1 1 calc R . . . .
C6 C 0.6202(5) 0.1216(3) 0.1828(3) 0.0638(9) Uani 1 1 d . . . . .
H6 H 0.484925 0.165306 0.166097 0.077 Uiso 1 1 calc R . . . .
C21 C 0.7001(6) 0.3002(4) 0.5129(2) 0.0734(10) Uani 1 1 d . . . . .
H21A H 0.814626 0.346000 0.513033 0.110 Uiso 1 1 calc GR . . . .
H21B H 0.717166 0.210717 0.562690 0.110 Uiso 1 1 calc GR . . . .
H21C H 0.571419 0.356126 0.527544 0.110 Uiso 1 1 calc GR . . . .
C5 C 0.7648(6) 0.0929(4) 0.1097(3) 0.0809(11) Uani 1 1 d . . . . .
H5 H 0.726981 0.116339 0.044191 0.097 Uiso 1 1 calc R . . . .
C20 C 1.0213(5) 0.3759(4) 0.2038(3) 0.0821(12) Uani 1 1 d . . . . .
H20A H 1.105312 0.309496 0.254857 0.123 Uiso 1 1 calc GR . . . .
H20B H 1.109229 0.429698 0.153797 0.123 Uiso 1 1 calc GR . . . .
H20C H 0.948932 0.327505 0.173645 0.123 Uiso 1 1 calc GR . . . .
C18 C 0.5141(6) 0.7300(4) 0.2083(3) 0.0991(14) Uani 1 1 d . . . . .
H18A H 0.424176 0.679573 0.259305 0.149 Uiso 1 1 calc GR . . . .
H18B H 0.431359 0.797752 0.157314 0.149 Uiso 1 1 calc GR . . . .
H18C H 0.592609 0.776512 0.237092 0.149 Uiso 1 1 calc GR . . . .
C19 C 0.9608(6) 0.5768(5) 0.3304(3) 0.0940(13) Uani 1 1 d . . . . .
H19A H 0.858191 0.628827 0.365209 0.141 Uiso 1 1 calc GR . . . .
H19B H 1.044970 0.638446 0.284460 0.141 Uiso 1 1 calc GR . . . .
H19C H 1.048064 0.505573 0.377586 0.141 Uiso 1 1 calc GR . . . .
C16 C 0.8082(6) 0.7098(4) 0.0797(3) 0.0976(14) Uani 1 1 d . . . . .
H16A H 0.886957 0.755806 0.108745 0.146 Uiso 1 1 calc GR . . . .
H16B H 0.723653 0.778051 0.029689 0.146 Uiso 1 1 calc GR . . . .
H16C H 0.902223 0.647289 0.049547 0.146 Uiso 1 1 calc GR . . . .
C17 C 0.5458(7) 0.5545(5) 0.1137(4) 0.1149(16) Uani 1 1 d . . . . .
H17A H 0.641797 0.494607 0.082095 0.172 Uiso 1 1 calc GR . . . .
H17B H 0.459781 0.623265 0.064539 0.172 Uiso 1 1 calc GR . . . .
H17C H 0.459285 0.499903 0.163940 0.172 Uiso 1 1 calc GR . . . .


_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
Si14 O13 1.655(2) . ?
Si14 C15 1.863(3) . ?
Si14 C20 1.866(3) . ?
Si14 C19 1.858(4) . ?
O13 C12 1.400(3) . ?
N11 N10 1.356(3) . ?
N11 C7 1.339(4) . ?
N11 C12 1.474(3) . ?
N8 C7 1.320(3) . ?
N8 N9 1.362(4) . ?
N10 N9 1.290(4) . ?
C7 C1 1.472(4) . ?
C1 C2 1.392(4) . ?
C1 C6 1.373(4) . ?
C12 H12 0.9800 . ?
C12 C21 1.497(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.365(4) . ?
C15 C18 1.555(4) . ?
C15 C16 1.540(5) . ?
C15 C17 1.514(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(5) . ?
C6 H6 0.9300 . ?
C6 C5 1.377(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C5 H5 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
O13 Si14 C15 103.82(12) . . ?
O13 Si14 C20 110.55(14) . . ?
O13 Si14 C19 109.44(15) . . ?
C15 Si14 C20 109.96(17) . . ?
C19 Si14 C15 112.23(18) . . ?
C19 Si14 C20 110.65(18) . . ?
C12 O13 Si14 127.49(16) . . ?
N10 N11 C12 121.3(2) . . ?
C7 N11 N10 108.3(2) . . ?
C7 N11 C12 130.2(2) . . ?
C7 N8 N9 105.2(3) . . ?
N9 N10 N11 105.9(3) . . ?
N11 C7 C1 126.2(2) . . ?
N8 C7 N11 109.0(3) . . ?
N8 C7 C1 124.7(3) . . ?
N10 N9 N8 111.7(2) . . ?
C2 C1 C7 121.0(3) . . ?
C6 C1 C7 119.4(3) . . ?
C6 C1 C2 119.6(3) . . ?
O13 C12 N11 106.8(2) . . ?
O13 C12 H12 108.8 . . ?
O13 C12 C21 112.8(3) . . ?
N11 C12 H12 108.8 . . ?
N11 C12 C21 110.7(2) . . ?
C21 C12 H12 108.8 . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C18 C15 Si14 109.6(2) . . ?
C16 C15 Si14 110.2(2) . . ?
C16 C15 C18 108.5(3) . . ?
C17 C15 Si14 110.0(2) . . ?
C17 C15 C18 110.3(3) . . ?
C17 C15 C16 108.2(3) . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.9(3) . . ?
C5 C4 H4 120.0 . . ?
C1 C6 H6 119.7 . . ?
C1 C6 C5 120.7(3) . . ?
C5 C6 H6 119.7 . . ?
C12 C21 H21A 109.5 . . ?
C12 C21 H21B 109.5 . . ?
C12 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
Si14 C20 H20A 109.5 . . ?
Si14 C20 H20B 109.5 . . ?
Si14 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
Si14 C19 H19A 109.5 . . ?
Si14 C19 H19B 109.5 . . ?
Si14 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
Si14 O13 C12 N11 -142.61(19) . . . . ?
Si14 O13 C12 C21 95.5(3) . . . . ?
O13 Si14 C15 C18 64.8(3) . . . . ?
O13 Si14 C15 C16 -175.8(2) . . . . ?
O13 Si14 C15 C17 -56.6(3) . . . . ?
N11 N10 N9 N8 -0.9(3) . . . . ?
N11 C7 C1 C2 58.7(4) . . . . ?
N11 C7 C1 C6 -119.9(3) . . . . ?
N8 C7 C1 C2 -125.7(3) . . . . ?
N8 C7 C1 C6 55.7(4) . . . . ?
N10 N11 C7 N8 0.1(3) . . . . ?
N10 N11 C7 C1 176.3(2) . . . . ?
N10 N11 C12 O13 -90.1(3) . . . . ?
N10 N11 C12 C21 33.0(3) . . . . ?
C7 N11 N10 N9 0.5(3) . . . . ?
C7 N11 C12 O13 84.0(3) . . . . ?
C7 N11 C12 C21 -152.8(3) . . . . ?
C7 N8 N9 N10 1.0(3) . . . . ?
C7 C1 C2 C3 -179.2(3) . . . . ?
C7 C1 C6 C5 179.1(3) . . . . ?
N9 N8 C7 N11 -0.7(3) . . . . ?
N9 N8 C7 C1 -176.9(3) . . . . ?
C1 C2 C3 C4 0.7(5) . . . . ?
C1 C6 C5 C4 -0.6(5) . . . . ?
C12 N11 N10 N9 175.8(2) . . . . ?
C12 N11 C7 N8 -174.6(2) . . . . ?
C12 N11 C7 C1 1.6(5) . . . . ?
C2 C1 C6 C5 0.5(5) . . . . ?
C2 C3 C4 C5 -0.8(5) . . . . ?
C3 C4 C5 C6 0.8(6) . . . . ?
C15 Si14 O13 C12 166.7(2) . . . . ?
C6 C1 C2 C3 -0.6(5) . . . . ?
C20 Si14 O13 C12 48.9(3) . . . . ?
C20 Si14 C15 C18 -176.9(2) . . . . ?
C20 Si14 C15 C16 -57.5(3) . . . . ?
C20 Si14 C15 C17 61.7(3) . . . . ?
C19 Si14 O13 C12 -73.3(3) . . . . ?
C19 Si14 C15 C18 -53.3(3) . . . . ?
C19 Si14 C15 C16 66.1(3) . . . . ?
C19 Si14 C15 C17 -174.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.285
_oxdiff_exptl_absorpt_empirical_full_min 0.676
