# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1865223'
_audit_update_record             
;
2018-08-31 deposited with the CCDC.
2018-11-19 downloaded from the CCDC.
;

_audit_creation_date             2018-08-28T14:48:30-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C38 H22 N10 Si, 0.84(O)'
_chemical_formula_sum            'C38 H22 N10 O0.84 Si'
_chemical_formula_weight         660.19
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P -4 n 2'
_symmetry_space_group_name_Hall  'P -4 -2n'
_symmetry_Int_Tables_number      118
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'y, -x, -z'
'-x, -y, z'
'-y, x, -z'
'y+1/2, x+1/2, -z+1/2'
'-y+1/2, -x+1/2, -z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   9.7375(10)
_cell_length_b                   9.7375(10)
_cell_length_c                   15.684(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1487.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    105(2)
_cell_measurement_reflns_used    1142
_cell_measurement_theta_min      4.368
_cell_measurement_theta_max      27.25
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       irregular
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             681.4

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.69329
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_ambient_temperature      105(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.4419
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.000899
_diffrn_orient_matrix_ub_12      0.0653623
_diffrn_orient_matrix_ub_13      0.0200147
_diffrn_orient_matrix_ub_21      -0.0212476
_diffrn_orient_matrix_ub_22      0.0305431
_diffrn_orient_matrix_ub_23      -0.0388331
_diffrn_orient_matrix_ub_31      -0.0696186
_diffrn_orient_matrix_ub_32      -0.0101598
_diffrn_orient_matrix_ub_33      0.0117711
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.064
_diffrn_reflns_number            3899
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.938
_diffrn_reflns_theta_max         28.562
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.889
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.846
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.792
_reflns_Friedel_coverage         0.706
_reflns_number_total             1612
_reflns_number_gt                1452
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0310P)²+2.8347P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1612
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0783
_refine_ls_wR_factor_ref         0.1665
_refine_ls_wR_factor_gt          0.1626
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_restrained_S_all      1.195
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 470 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.24(19)
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.068

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 1 1 0.5 0.0242(6) Uani 1 4 d S T P . .
N3 N 0.8744(6) 0.6574(6) 0.3862(3) 0.0341(13) Uani 1 1 d . . . . .
N2 N 0.9332(5) 0.8219(5) 0.4836(3) 0.0241(10) Uani 1 1 d . . . . .
N1 N 1 1 0.3805(3) 0.0300(14) Uani 1 2 d S T P . .
C6 C 0.8872(6) 0.7103(6) 0.5290(4) 0.0284(13) Uani 1 1 d . . . . .
C7 C 0.8728(7) 0.6863(7) 0.6169(4) 0.0378(16) Uani 1 1 d . . . . .
H7 H 0.895643 0.754316 0.65789 0.045 Uiso 1 1 calc R U . . .
C3 C 0.9593(7) 0.8861(7) 0.3385(3) 0.0316(14) Uani 1 1 d . . . . .
C10 C 0.7986(6) 0.4800(6) 0.4938(5) 0.0354(14) Uani 1 1 d . . . . .
H10 H 0.770961 0.412585 0.45353 0.042 Uiso 1 1 calc R U . . .
C2 C 0.9596(7) 0.8816(7) 0.2500(4) 0.0417(17) Uani 1 1 d . . . . .
H2 H 0.933405 0.800947 0.220004 0.05 Uiso 1 1 calc R U . . .
C5 C 0.8522(6) 0.6081(7) 0.4689(4) 0.0296(13) Uani 1 1 d . . . . .
C4 C 0.9223(6) 0.7808(6) 0.3996(4) 0.0276(13) Uani 1 1 d . . . . .
C1 C 1 1 0.2068(5) 0.045(2) Uani 1 2 d S T P . .
H1 H 0.999999 1.000001 0.146253 0.054 Uiso 1 2 calc R U P . .
C9 C 0.7888(8) 0.4590(7) 0.5802(5) 0.0477(19) Uani 1 1 d . . . . .
H9 H 0.756837 0.372744 0.60049 0.057 Uiso 1 1 calc R U . . .
C8 C 0.8248(8) 0.5617(8) 0.6401(4) 0.0468(19) Uani 1 1 d . . . . .
H8 H 0.814868 0.54206 0.699071 0.056 Uiso 1 1 calc R U . . .
O1 O 0.4037(18) 0.0963(18) 0.75 0.076(9) Uani 0.42(3) 2 d S T . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si1 N2 1.870(5) . ?
Si1 N2 1.870(5) 3_775 ?
Si1 N2 1.870(5) 4_756 ?
Si1 N2 1.870(5) 2_576 ?
Si1 N1 1.874(5) 2_576 ?
Si1 N1 1.874(5) . ?
N3 C4 1.306(8) . ?
N3 C5 1.401(8) . ?
N2 C6 1.375(7) . ?
N2 C4 1.381(7) . ?
N1 C3 1.350(7) . ?
N1 C3 1.350(7) 3_775 ?
C6 C7 1.405(8) . ?
C6 C5 1.412(8) . ?
C7 C8 1.350(10) . ?
C7 H7 0.95 . ?
C3 C2 1.389(8) . ?
C3 C4 1.449(8) . ?
C10 C9 1.374(10) . ?
C10 C5 1.407(9) . ?
C10 H10 0.95 . ?
C2 C1 1.394(7) . ?
C2 H2 0.95 . ?
C1 H1 0.95 . ?
C9 C8 1.415(10) . ?
C9 H9 0.95 . ?
C8 H8 0.95 . ?

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 Si1 N2 164.2(3) . 3_775 ?
N2 Si1 N2 91.09(4) . 4_756 ?
N2 Si1 N2 91.09(4) 3_775 4_756 ?
N2 Si1 N2 91.09(4) . 2_576 ?
N2 Si1 N2 91.09(4) 3_775 2_576 ?
N2 Si1 N2 164.2(3) 4_756 2_576 ?
N2 Si1 N1 97.92(13) . 2_576 ?
N2 Si1 N1 97.92(13) 3_775 2_576 ?
N2 Si1 N1 82.08(13) 4_756 2_576 ?
N2 Si1 N1 82.08(13) 2_576 2_576 ?
N2 Si1 N1 82.08(13) . . ?
N2 Si1 N1 82.08(13) 3_775 . ?
N2 Si1 N1 97.92(13) 4_756 . ?
N2 Si1 N1 97.92(13) 2_576 . ?
N1 Si1 N1 180 2_576 . ?
C4 N3 C5 102.7(5) . . ?
C6 N2 C4 103.9(5) . . ?
C6 N2 Si1 140.8(4) . . ?
C4 N2 Si1 115.3(4) . . ?
C3 N1 C3 121.6(6) . 3_775 ?
C3 N1 Si1 119.2(3) . . ?
C3 N1 Si1 119.2(3) 3_775 . ?
N2 C6 C7 132.2(6) . . ?
N2 C6 C5 106.9(5) . . ?
C7 C6 C5 120.9(6) . . ?
C8 C7 C6 116.6(6) . . ?
C8 C7 H7 121.7 . . ?
C6 C7 H7 121.7 . . ?
N1 C3 C2 120.9(6) . . ?
N1 C3 C4 109.4(5) . . ?
C2 C3 C4 129.8(6) . . ?
C9 C10 C5 115.5(6) . . ?
C9 C10 H10 122.2 . . ?
C5 C10 H10 122.2 . . ?
C3 C2 C1 117.4(6) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
N3 C5 C10 128.1(6) . . ?
N3 C5 C6 109.9(5) . . ?
C10 C5 C6 122.0(5) . . ?
N3 C4 N2 116.6(5) . . ?
N3 C4 C3 129.2(5) . . ?
N2 C4 C3 114.0(5) . . ?
C2 C1 C2 121.9(7) . 3_775 ?
C2 C1 H1 119 . . ?
C2 C1 H1 119 3_775 . ?
C10 C9 C8 122.1(6) . . ?
C10 C9 H9 119 . . ?
C8 C9 H9 119 . . ?
C7 C8 C9 122.8(6) . . ?
C7 C8 H8 118.6 . . ?
C9 C8 H8 118.6 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
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# END of CIF
