# Electronic Supplementary Material (ESI) for MedChemComm.
# 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_mbfcmb
_database_code_depnum_ccdc_archive 'CCDC 1582898'
_audit_update_record             
;
2017-10-30 deposited with the CCDC.
2018-01-19 downloaded from the CCDC.
;
_nottingham_internal_coll_name   MBFCMB
_nottingham_internal_coll_number 14595
_nottingham_internal_coll_client MBF/CJM
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time '20.0000, 80.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   13/03/2015
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'SN, XDA 017/09'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 01/04/2015
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 1/4/2015
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 1/4/2015
_nottingham_internal_refinement_user pczwl
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 1/4/2015
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 2/4/2015
_refine_special_details          
'The crystal was determined to be a two-component psuedo-merohedral twin using PLATON TWINROTMATR. An HKLF5 style file was produced with PLATON against which subsequent refinement was performed.'
_audit_creation_date             2015-04-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H14 N6 O2 Si'
_chemical_formula_sum            'C9 H14 N6 O2 Si'
_chemical_formula_weight         266.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C9 H14 N6 O2 Si'
_chemical_oxdiff_usercomment     
'MBFCMB #14595 SN-463 IN FOMBLIN FILM ON A MICROMOUNT FOR MBF/CJM'
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'

_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                   6.0637(7)
_cell_length_b                   6.3295(8)
_cell_length_c                   17.0569(17)
_cell_angle_alpha                82.559(9)
_cell_angle_beta                 81.097(9)
_cell_angle_gamma                72.642(10)
_cell_volume                     614.88(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2090
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.9770
_cell_measurement_theta_min      7.3740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.768
_exptl_absorpt_correction_T_max  0.898
_exptl_absorpt_correction_T_min  0.613
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.3771
_exptl_crystal_size_mid          0.2509
_exptl_crystal_size_min          0.0598
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2327
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.613
_diffrn_reflns_theta_min         5.270
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3613
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -112.00  -15.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -77.0000 -120.0000 97

#__ type_ start__ end____ width___ exp.time_
  2 omega  -11.00   18.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   77.0000    0.0000 29

#__ type_ start__ end____ width___ exp.time_
  3 omega  -66.00  -21.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   77.0000    0.0000 45

#__ type_ start__ end____ width___ exp.time_
  4 omega  -29.00    4.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6277  -38.0000   90.0000 33

#__ type_ start__ end____ width___ exp.time_
  5 omega   27.00   54.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6277 -125.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega    6.00   55.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6277  -38.0000   90.0000 49

#__ type_ start__ end____ width___ exp.time_
  7 omega   65.00  115.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822 -125.0000   60.0000 50

#__ type_ start__ end____ width___ exp.time_
  8 omega   33.00   86.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822  -30.0000  -60.0000 53

#__ type_ start__ end____ width___ exp.time_
  9 omega   62.00  137.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   15.0000  -90.0000 75

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00  125.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822  -77.0000 -150.0000 87

#__ type_ start__ end____ width___ exp.time_
 11 omega   32.00   63.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822  -95.0000  150.0000 31

#__ type_ start__ end____ width___ exp.time_
 12 omega   64.00  105.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822  -95.0000  150.0000 41

#__ type_ start__ end____ width___ exp.time_
 13 omega   56.00   89.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822  -30.0000 -120.0000 33

#__ type_ start__ end____ width___ exp.time_
 14 omega   84.00  146.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   30.0000  -60.0000 62

#__ type_ start__ end____ width___ exp.time_
 15 omega   37.00   69.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822  -30.0000  120.0000 32

#__ type_ start__ end____ width___ exp.time_
 16 omega  147.00  176.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   30.0000  -60.0000 29

#__ type_ start__ end____ width___ exp.time_
 17 omega   33.00   80.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822  -30.0000   30.0000 47

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00  108.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822  -95.0000   60.0000 76

#__ type_ start__ end____ width___ exp.time_
 19 omega   16.00  113.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6277   57.0000  150.0000 97

#__ type_ start__ end____ width___ exp.time_
 20 omega   11.00   50.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6277   77.0000  -30.0000 39

#__ type_ start__ end____ width___ exp.time_
 21 omega   20.00  115.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6277   38.0000   90.0000 95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_UB_11      0.1388861000
_diffrn_orient_matrix_UB_12      -0.2476376000
_diffrn_orient_matrix_UB_13      0.0051437000
_diffrn_orient_matrix_UB_21      0.0665283000
_diffrn_orient_matrix_UB_22      0.0161253000
_diffrn_orient_matrix_UB_23      -0.0910239000
_diffrn_orient_matrix_UB_31      0.2195961000
_diffrn_orient_matrix_UB_32      0.0629061000
_diffrn_orient_matrix_UB_33      0.0105690000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2020
_reflns_number_total             2327
_reflns_odcompleteness_completeness 96.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 _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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.929
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2327
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0825
_refine_ls_restrained_S_all      1.074
_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)+(0.0838P)²+2.9197P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2166
_refine_ls_wR_factor_ref         0.2225
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.867(6) 0.133(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 N18-H18B = N18-H18A
 0.88 with sigma of 0.02
4.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
4.b Aromatic/amide H refined with riding coordinates:
 C8(H8)
4.c Idealised Me refined as rotating group:
 C13(H13A,H13C,H13B), C14(H14C,H14A,H14B), C15(H15C,H15A,H15B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 0.1083(8) 0.2725(8) 0.6371(3) 0.0242(9) Uani 1 1 d . . . . .
N2 N 0.1771(7) 0.1895(6) 0.7106(2) 0.0249(8) Uani 1 1 d . . . . .
N3 N 0.1393(7) 0.0000(6) 0.7537(2) 0.0262(8) Uani 1 1 d . . . . .
N4 N 0.0179(7) -0.1048(6) 0.7292(2) 0.0259(8) Uani 1 1 d . . . . .
C5 C -0.0802(8) -0.0242(7) 0.6606(3) 0.0227(9) Uani 1 1 d . . . . .
C6 C -0.2356(8) -0.0817(7) 0.6219(3) 0.0232(9) Uani 1 1 d . . . . .
N7 N -0.2846(7) 0.0652(6) 0.5556(2) 0.0244(8) Uani 1 1 d . . . . .
C8 C -0.1634(8) 0.2067(8) 0.5523(3) 0.0252(10) Uani 1 1 d . . . . .
H8 H -0.1635 0.3251 0.5118 0.030 Uiso 1 1 calc R . . . .
N9 N -0.0359(7) 0.1600(6) 0.6155(2) 0.0229(8) Uani 1 1 d . . . . .
O10 O 0.1643(6) 0.4228(5) 0.59548(19) 0.0271(7) Uani 1 1 d . . . . .
C11 C 0.2959(9) 0.3110(8) 0.7493(3) 0.0280(10) Uani 1 1 d . . . . .
H11A H 0.2170 0.4717 0.7401 0.034 Uiso 1 1 calc R . . . .
H11B H 0.4571 0.2848 0.7221 0.034 Uiso 1 1 calc R . . . .
Si12 Si 0.3112(2) 0.2417(2) 0.86055(8) 0.0273(4) Uani 1 1 d . . . . .
C13 C 0.3880(10) 0.4855(9) 0.8870(3) 0.0381(12) Uani 1 1 d . . . . .
H13A H 0.4044 0.4680 0.9440 0.057 Uiso 1 1 calc GR . . . .
H13C H 0.2647 0.6217 0.8752 0.057 Uiso 1 1 calc GR . . . .
H13B H 0.5354 0.4948 0.8559 0.057 Uiso 1 1 calc GR . . . .
C14 C 0.5453(10) -0.0198(9) 0.8791(4) 0.0391(12) Uani 1 1 d . . . . .
H14C H 0.5234 -0.1376 0.8517 0.059 Uiso 1 1 calc GR . . . .
H14A H 0.5388 -0.0637 0.9365 0.059 Uiso 1 1 calc GR . . . .
H14B H 0.6972 0.0040 0.8590 0.059 Uiso 1 1 calc GR . . . .
C15 C 0.0282(11) 0.2332(12) 0.9173(4) 0.0500(16) Uani 1 1 d . . . . .
H15C H 0.0385 0.2245 0.9745 0.075 Uiso 1 1 calc GR . . . .
H15A H -0.0115 0.1026 0.9054 0.075 Uiso 1 1 calc GR . . . .
H15B H -0.0926 0.3681 0.9022 0.075 Uiso 1 1 calc GR . . . .
C16 C -0.3436(8) -0.2668(8) 0.6451(3) 0.0245(9) Uani 1 1 d . . . . .
O17 O -0.2916(6) -0.4010(6) 0.7025(2) 0.0289(8) Uani 1 1 d . . . . .
N18 N -0.5024(7) -0.2701(7) 0.5984(2) 0.0279(9) Uani 1 1 d D . . . .
H18A H -0.579(9) -0.370(8) 0.605(3) 0.034 Uiso 1 1 d DR . . . .
H18B H -0.516(10) -0.207(9) 0.5498(17) 0.034 Uiso 1 1 d DR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.372(6) . ?
C1 N9 1.395(6) . ?
C1 O10 1.211(6) . ?
N2 N3 1.384(5) . ?
N2 C11 1.468(6) . ?
N3 N4 1.271(5) . ?
N4 C5 1.366(6) . ?
C5 C6 1.384(6) . ?
C5 N9 1.383(6) . ?
C6 N7 1.379(6) . ?
C6 C16 1.488(6) . ?
N7 C8 1.309(6) . ?
C8 H8 0.9500 . ?
C8 N9 1.374(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 Si12 1.902(5) . ?
Si12 C13 1.865(5) . ?
Si12 C14 1.859(6) . ?
Si12 C15 1.847(6) . ?
C13 H13A 0.9800 . ?
C13 H13C 0.9800 . ?
C13 H13B 0.9800 . ?
C14 H14C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C16 O17 1.225(6) . ?
C16 N18 1.347(6) . ?
N18 H18A 0.88(2) . ?
N18 H18B 0.88(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
N2 C1 N9 111.1(4) . . ?
O10 C1 N2 125.3(4) . . ?
O10 C1 N9 123.6(4) . . ?
C1 N2 N3 125.5(4) . . ?
C1 N2 C11 118.7(4) . . ?
N3 N2 C11 115.8(4) . . ?
N4 N3 N2 120.8(4) . . ?
N3 N4 C5 118.9(4) . . ?
N4 C5 C6 133.9(4) . . ?
N4 C5 N9 120.7(4) . . ?
N9 C5 C6 105.3(4) . . ?
C5 C6 C16 128.2(4) . . ?
N7 C6 C5 109.2(4) . . ?
N7 C6 C16 122.5(4) . . ?
C8 N7 C6 107.4(4) . . ?
N7 C8 H8 124.8 . . ?
N7 C8 N9 110.4(4) . . ?
N9 C8 H8 124.8 . . ?
C5 N9 C1 122.6(4) . . ?
C8 N9 C1 129.8(4) . . ?
C8 N9 C5 107.6(4) . . ?
N2 C11 H11A 108.0 . . ?
N2 C11 H11B 108.0 . . ?
N2 C11 Si12 117.3(3) . . ?
H11A C11 H11B 107.2 . . ?
Si12 C11 H11A 108.0 . . ?
Si12 C11 H11B 108.0 . . ?
C13 Si12 C11 101.4(2) . . ?
C14 Si12 C11 110.2(3) . . ?
C14 Si12 C13 110.9(3) . . ?
C15 Si12 C11 112.9(3) . . ?
C15 Si12 C13 108.7(3) . . ?
C15 Si12 C14 112.2(3) . . ?
Si12 C13 H13A 109.5 . . ?
Si12 C13 H13C 109.5 . . ?
Si12 C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13C C13 H13B 109.5 . . ?
Si12 C14 H14C 109.5 . . ?
Si12 C14 H14A 109.5 . . ?
Si12 C14 H14B 109.5 . . ?
H14C C14 H14A 109.5 . . ?
H14C C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
Si12 C15 H15C 109.5 . . ?
Si12 C15 H15A 109.5 . . ?
Si12 C15 H15B 109.5 . . ?
H15C C15 H15A 109.5 . . ?
H15C C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O17 C16 C6 121.8(4) . . ?
O17 C16 N18 124.0(4) . . ?
N18 C16 C6 114.2(4) . . ?
C16 N18 H18A 124(4) . . ?
C16 N18 H18B 127(4) . . ?
H18A N18 H18B 106(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
C1 N2 N3 N4 -5.4(7) . . . . ?
C1 N2 C11 Si12 163.0(3) . . . . ?
N2 C1 N9 C5 -5.8(6) . . . . ?
N2 C1 N9 C8 171.3(4) . . . . ?
N2 N3 N4 C5 -1.7(6) . . . . ?
N3 N2 C11 Si12 -15.5(5) . . . . ?
N3 N4 C5 C6 -172.8(5) . . . . ?
N3 N4 C5 N9 4.3(6) . . . . ?
N4 C5 C6 N7 177.0(5) . . . . ?
N4 C5 C6 C16 -1.9(8) . . . . ?
N4 C5 N9 C1 -0.2(7) . . . . ?
N4 C5 N9 C8 -177.9(4) . . . . ?
C5 C6 N7 C8 0.7(5) . . . . ?
C5 C6 C16 O17 -4.0(7) . . . . ?
C5 C6 C16 N18 175.2(4) . . . . ?
C6 C5 N9 C1 177.7(4) . . . . ?
C6 C5 N9 C8 0.0(5) . . . . ?
C6 N7 C8 N9 -0.7(5) . . . . ?
N7 C6 C16 O17 177.2(4) . . . . ?
N7 C6 C16 N18 -3.6(6) . . . . ?
N7 C8 N9 C1 -177.0(4) . . . . ?
N7 C8 N9 C5 0.5(5) . . . . ?
N9 C1 N2 N3 8.7(6) . . . . ?
N9 C1 N2 C11 -169.6(4) . . . . ?
N9 C5 C6 N7 -0.4(5) . . . . ?
N9 C5 C6 C16 -179.4(4) . . . . ?
O10 C1 N2 N3 -171.0(4) . . . . ?
O10 C1 N2 C11 10.7(7) . . . . ?
O10 C1 N9 C5 173.9(4) . . . . ?
O10 C1 N9 C8 -9.0(8) . . . . ?
C11 N2 N3 N4 173.0(4) . . . . ?
C16 C6 N7 C8 179.7(4) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1 1 0 0.0934 -1.0021 0.9966 -0.0089 -0.3860 -0.0498 -0.1575
1 -1 0 0.1574 1.0021 -0.9966 0.0089 0.3860 0.0498 0.1575
1 1 1 0.1671 0.9980 1.0002 1.0123 -0.1039 -0.0096 0.2928
-1 -1 -1 0.1911 -0.9980 -1.0002 -1.0123 0.1039 0.0096 -0.2928
0 0 -1 0.0459 0.0010 0.0011 -0.9992 -0.0053 0.0910 -0.0103
0 0 1 0.0139 -0.0010 -0.0011 0.9992 0.0053 -0.0910 0.0103
1 4 2 0.1591 0.9922 3.9959 2.0179 -0.8413 -0.0532 0.4906

_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.867(6)
2 0.133(6)

_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_mbfcme
_database_code_depnum_ccdc_archive 'CCDC 1582899'
_audit_update_record             
;
2017-10-30 deposited with the CCDC.
2018-01-19 downloaded from the CCDC.
;
_nottingham_internal_coll_name   MBFCME
_nottingham_internal_coll_number 14847
_nottingham_internal_coll_client MBF/CJM
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time '3.0000, 2.0000'
_nottingham_internal_coll_frame_width 2.0000
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   04/06/2015
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'SN, XDA 017/09'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 04/06/2015
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 4/6/2015
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 4/6/2015
_nottingham_internal_refinement_user pczwl
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 4/6/2015
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 4/6/2015
_refine_special_details          ?
_audit_creation_date             2015-06-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H18 N6 O3 Si'
_chemical_formula_sum            'C11 H18 N6 O3 Si'
_chemical_formula_weight         310.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H18 N6 O3 Si'
_chemical_oxdiff_usercomment     
'MBFCME #14847 SN-566 IN FOMBLIN FILM ON A MICROMOUNT FOR MBF/CJM'
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'

_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                   7.5168(10)
_cell_length_b                   9.0109(15)
_cell_length_c                   11.4120(15)
_cell_angle_alpha                88.485(12)
_cell_angle_beta                 78.814(11)
_cell_angle_gamma                86.275(12)
_cell_volume                     756.61(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2659
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.1440
_cell_measurement_theta_min      5.9260
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.565
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_correction_T_min  0.681
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.3666
_exptl_crystal_size_mid          0.2579
_exptl_crystal_size_min          0.0469
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5157
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.116
_diffrn_reflns_theta_min         4.919
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.1806
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   52.00  114.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5072 -125.0000   60.0000 31

#__ type_ start__ end____ width___ exp.time_
  2 omega   97.00  123.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5072  -77.0000  -30.0000 13

#__ type_ start__ end____ width___ exp.time_
  3 omega   74.00  176.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5072   15.0000  -90.0000 51

#__ type_ start__ end____ width___ exp.time_
  4 omega  110.00  168.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5072  125.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  5 omega   94.00  168.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5072  125.0000  -90.0000 37

#__ type_ start__ end____ width___ exp.time_
  6 omega  150.00  176.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5072  125.0000 -150.0000 13

#__ type_ start__ end____ width___ exp.time_
  7 omega   80.00  170.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5072   61.0000  -30.0000 45

#__ type_ start__ end____ width___ exp.time_
  8 omega   53.00   95.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5072  -45.0000 -180.0000 21

#__ type_ start__ end____ width___ exp.time_
  9 omega   87.00  121.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5072 -125.0000 -180.0000 17

#__ type_ start__ end____ width___ exp.time_
 10 omega   46.00   84.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5072  -30.0000  -60.0000 19

#__ type_ start__ end____ width___ exp.time_
 11 omega   50.00   84.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5072  -30.0000  -30.0000 17

#__ type_ start__ end____ width___ exp.time_
 12 omega   41.00   81.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5072  -77.0000  -30.0000 20

#__ type_ start__ end____ width___ exp.time_
 13 omega   36.00   98.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5072  -45.0000   30.0000 31

#__ type_ start__ end____ width___ exp.time_
 14 omega   37.00   95.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5072  -77.0000 -180.0000 29

#__ type_ start__ end____ width___ exp.time_
 15 omega  -46.00   28.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000 -180.0000 37

#__ type_ start__ end____ width___ exp.time_
 16 omega  -64.00   32.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   57.0000   30.0000 48

#__ type_ start__ end____ width___ exp.time_
 17 omega  -89.00  -33.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  125.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
 18 omega -106.00  -16.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -57.0000 -120.0000 45
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova-Duo, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_UB_11      0.0248966000
_diffrn_orient_matrix_UB_12      -0.1710492000
_diffrn_orient_matrix_UB_13      0.0015387000
_diffrn_orient_matrix_UB_21      -0.0323212000
_diffrn_orient_matrix_UB_22      -0.0029979000
_diffrn_orient_matrix_UB_23      -0.1291334000
_diffrn_orient_matrix_UB_31      0.2052922000
_diffrn_orient_matrix_UB_32      0.0096127000
_diffrn_orient_matrix_UB_33      -0.0475628000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2656
_reflns_number_total             2945
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.060
_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     193
_refine_ls_number_reflns         2945
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0410
_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)+(0.0646P)²+0.2695P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1139
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8)
2.c X=CH2 refined with riding coordinates:
 N21(H21A,H21B)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 -0.1396(2) 0.26723(17) 1.00353(14) 0.0170(3) Uani 1 1 d . . . . .
N2 N -0.17529(19) 0.25543(15) 0.89071(12) 0.0178(3) Uani 1 1 d . . . . .
N3 N -0.25869(19) 0.36377(15) 0.82780(12) 0.0199(3) Uani 1 1 d . . . . .
N4 N -0.30389(18) 0.49184(15) 0.87204(12) 0.0185(3) Uani 1 1 d . . . . .
C5 C -0.2703(2) 0.51990(17) 0.98287(14) 0.0160(3) Uani 1 1 d . . . . .
C6 C -0.2968(2) 0.64374(18) 1.05408(14) 0.0161(3) Uani 1 1 d . . . . .
N7 N -0.23598(19) 0.61072(15) 1.15878(12) 0.0190(3) Uani 1 1 d . . . . .
C8 C -0.1760(2) 0.47073(18) 1.15285(15) 0.0193(3) Uani 1 1 d . . . . .
H8 H -0.1277 0.4183 1.2141 0.023 Uiso 1 1 calc R . . . .
N9 N -0.19194(18) 0.41006(15) 1.04770(12) 0.0161(3) Uani 1 1 d . . . . .
O10 O -0.06991(17) 0.17191(13) 1.05825(11) 0.0231(3) Uani 1 1 d . . . . .
C11 C -0.1286(2) 0.11377(18) 0.82735(15) 0.0202(4) Uani 1 1 d . . . . .
H11A H -0.1378 0.0309 0.8865 0.024 Uiso 1 1 calc R . . . .
H11B H -0.2175 0.1003 0.7755 0.024 Uiso 1 1 calc R . . . .
O12 O 0.04613(15) 0.10738(13) 0.75762(10) 0.0195(3) Uani 1 1 d . . . . .
C13 C 0.0615(2) 0.19592(19) 0.64917(15) 0.0209(3) Uani 1 1 d . . . . .
H13A H 0.0428 0.3029 0.6688 0.025 Uiso 1 1 calc R . . . .
H13B H -0.0326 0.1707 0.6044 0.025 Uiso 1 1 calc R . . . .
C14 C 0.2480(2) 0.16475(19) 0.57393(15) 0.0229(4) Uani 1 1 d . . . . .
H14A H 0.2654 0.0571 0.5568 0.027 Uiso 1 1 calc R . . . .
H14B H 0.3402 0.1894 0.6204 0.027 Uiso 1 1 calc R . . . .
Si15 Si 0.28769(6) 0.27221(5) 0.42821(4) 0.01932(15) Uani 1 1 d . . . . .
C16 C 0.2730(3) 0.4751(2) 0.46091(18) 0.0289(4) Uani 1 1 d . . . . .
H16A H 0.3389 0.4919 0.5251 0.043 Uiso 1 1 calc GR . . . .
H16B H 0.1453 0.5098 0.4859 0.043 Uiso 1 1 calc GR . . . .
H16C H 0.3271 0.5300 0.3889 0.043 Uiso 1 1 calc GR . . . .
C17 C 0.5166(3) 0.2141(2) 0.34147(17) 0.0312(4) Uani 1 1 d . . . . .
H17A H 0.5362 0.2661 0.2639 0.047 Uiso 1 1 calc GR . . . .
H17B H 0.5245 0.1065 0.3290 0.047 Uiso 1 1 calc GR . . . .
H17C H 0.6097 0.2392 0.3858 0.047 Uiso 1 1 calc GR . . . .
C18 C 0.1093(3) 0.2300(2) 0.34240(16) 0.0274(4) Uani 1 1 d . . . . .
H18A H 0.1425 0.2683 0.2604 0.041 Uiso 1 1 calc GR . . . .
H18B H -0.0078 0.2775 0.3808 0.041 Uiso 1 1 calc GR . . . .
H18C H 0.0996 0.1222 0.3411 0.041 Uiso 1 1 calc GR . . . .
C19 C -0.3811(2) 0.79254(17) 1.03065(14) 0.0169(3) Uani 1 1 d . . . . .
O20 O -0.47237(16) 0.80814(13) 0.95143(11) 0.0219(3) Uani 1 1 d . . . . .
N21 N -0.35561(19) 0.90079(15) 1.10149(12) 0.0204(3) Uani 1 1 d . . . . .
H21A H -0.4054 0.9907 1.0936 0.024 Uiso 1 1 calc R . . . .
H21B H -0.2890 0.8825 1.1563 0.024 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.373(2) . ?
C1 N9 1.399(2) . ?
C1 O10 1.201(2) . ?
N2 N3 1.3854(19) . ?
N2 C11 1.472(2) . ?
N3 N4 1.271(2) . ?
N4 C5 1.370(2) . ?
C5 C6 1.379(2) . ?
C5 N9 1.389(2) . ?
C6 N7 1.379(2) . ?
C6 C19 1.486(2) . ?
N7 C8 1.311(2) . ?
C8 H8 0.9500 . ?
C8 N9 1.361(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 O12 1.396(2) . ?
O12 C13 1.444(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.509(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 Si15 1.8846(18) . ?
Si15 C16 1.8675(19) . ?
Si15 C17 1.8613(19) . ?
Si15 C18 1.8701(19) . ?
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 . ?
C19 O20 1.237(2) . ?
C19 N21 1.330(2) . ?
N21 H21A 0.8800 . ?
N21 H21B 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N9 110.50(14) . . ?
O10 C1 N2 126.36(15) . . ?
O10 C1 N9 123.12(16) . . ?
C1 N2 N3 126.77(13) . . ?
C1 N2 C11 119.24(13) . . ?
N3 N2 C11 113.96(13) . . ?
N4 N3 N2 120.19(14) . . ?
N3 N4 C5 118.89(14) . . ?
N4 C5 C6 133.84(15) . . ?
N4 C5 N9 121.02(14) . . ?
C6 C5 N9 105.14(14) . . ?
C5 C6 C19 128.42(15) . . ?
N7 C6 C5 109.66(14) . . ?
N7 C6 C19 121.89(15) . . ?
C8 N7 C6 106.51(14) . . ?
N7 C8 H8 124.3 . . ?
N7 C8 N9 111.32(14) . . ?
N9 C8 H8 124.3 . . ?
C5 N9 C1 122.55(14) . . ?
C8 N9 C1 130.08(14) . . ?
C8 N9 C5 107.36(13) . . ?
N2 C11 H11A 109.1 . . ?
N2 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
O12 C11 N2 112.58(13) . . ?
O12 C11 H11A 109.1 . . ?
O12 C11 H11B 109.1 . . ?
C11 O12 C13 113.69(12) . . ?
O12 C13 H13A 109.9 . . ?
O12 C13 H13B 109.9 . . ?
O12 C13 C14 108.91(13) . . ?
H13A C13 H13B 108.3 . . ?
C14 C13 H13A 109.9 . . ?
C14 C13 H13B 109.9 . . ?
C13 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
C13 C14 Si15 113.75(12) . . ?
H14A C14 H14B 107.7 . . ?
Si15 C14 H14A 108.8 . . ?
Si15 C14 H14B 108.8 . . ?
C16 Si15 C14 108.76(9) . . ?
C16 Si15 C18 110.02(9) . . ?
C17 Si15 C14 108.90(8) . . ?
C17 Si15 C16 110.46(9) . . ?
C17 Si15 C18 109.85(9) . . ?
C18 Si15 C14 108.81(8) . . ?
Si15 C16 H16A 109.5 . . ?
Si15 C16 H16B 109.5 . . ?
Si15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Si15 C17 H17A 109.5 . . ?
Si15 C17 H17B 109.5 . . ?
Si15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
Si15 C18 H18A 109.5 . . ?
Si15 C18 H18B 109.5 . . ?
Si15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O20 C19 C6 119.80(15) . . ?
O20 C19 N21 124.37(15) . . ?
N21 C19 C6 115.79(14) . . ?
C19 N21 H21A 120.0 . . ?
C19 N21 H21B 120.0 . . ?
H21A N21 H21B 120.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N21 H21A O20 0.88 2.08 2.9486(18) 170.9 2_477
N21 H21B O12 0.88 2.24 3.0700(19) 156.6 2_567

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
C1 N2 N3 N4 3.0(2) . . . . ?
C1 N2 C11 O12 -91.04(17) . . . . ?
N2 C1 N9 C5 0.6(2) . . . . ?
N2 C1 N9 C8 -177.67(15) . . . . ?
N2 N3 N4 C5 -0.6(2) . . . . ?
N2 C11 O12 C13 -74.63(17) . . . . ?
N3 N2 C11 O12 90.93(16) . . . . ?
N3 N4 C5 C6 178.14(16) . . . . ?
N3 N4 C5 N9 -1.4(2) . . . . ?
N4 C5 C6 N7 -179.41(16) . . . . ?
N4 C5 C6 C19 2.2(3) . . . . ?
N4 C5 N9 C1 1.4(2) . . . . ?
N4 C5 N9 C8 -179.97(14) . . . . ?
C5 C6 N7 C8 -0.70(18) . . . . ?
C5 C6 C19 O20 15.6(2) . . . . ?
C5 C6 C19 N21 -166.33(15) . . . . ?
C6 C5 N9 C1 -178.24(13) . . . . ?
C6 C5 N9 C8 0.36(17) . . . . ?
C6 N7 C8 N9 0.94(18) . . . . ?
N7 C6 C19 O20 -162.54(15) . . . . ?
N7 C6 C19 N21 15.5(2) . . . . ?
N7 C8 N9 C1 177.63(15) . . . . ?
N7 C8 N9 C5 -0.84(19) . . . . ?
N9 C1 N2 N3 -2.8(2) . . . . ?
N9 C1 N2 C11 179.44(13) . . . . ?
N9 C5 C6 N7 0.20(17) . . . . ?
N9 C5 C6 C19 -178.16(15) . . . . ?
O10 C1 N2 N3 178.67(15) . . . . ?
O10 C1 N2 C11 0.9(2) . . . . ?
O10 C1 N9 C5 179.16(14) . . . . ?
O10 C1 N9 C8 0.9(3) . . . . ?
C11 N2 N3 N4 -179.13(14) . . . . ?
C11 O12 C13 C14 -172.61(14) . . . . ?
O12 C13 C14 Si15 179.66(11) . . . . ?
C13 C14 Si15 C16 62.98(15) . . . . ?
C13 C14 Si15 C17 -176.59(13) . . . . ?
C13 C14 Si15 C18 -56.87(15) . . . . ?
C19 C6 N7 C8 177.78(14) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 1 0.0375 0.0015 -0.0039 0.9989 0.0022 -0.1290 -0.0472
0 0 -1 0.0095 -0.0015 0.0039 -0.9989 -0.0022 0.1290 0.0472
-3 4 1 0.1526 -3.0208 3.9623 1.0362 -0.7514 -0.0480 -0.6313
2 5 -1 0.1151 1.9656 5.0210 -0.9951 -0.8114 0.0499 0.4991
4 3 -1 0.0616 3.9763 3.0430 -1.0175 -0.4231 -0.0063 0.8939
0 -1 0 0.1655 0.0062 -0.9993 -0.0037 0.1711 0.0033 -0.0081
-5 -1 1 0.1295 -4.9879 -1.0548 1.0324 0.0578 0.0311 -1.0832
3 -5 0 0.1942 3.0285 -4.9655 -0.0410 0.9247 -0.0777 0.5760
5 1 -1 0.1229 4.9879 1.0548 -1.0324 -0.0578 -0.0311 1.0832
3 0 -5 0.0692 2.9897 0.0504 -5.0168 0.0581 0.5511 0.8529
-2 -1 -7 0.0566 -2.0028 -0.9927 -6.9811 0.1092 0.9692 -0.0887

_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1:1 water:acetone'
