# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_test1
_database_code_depnum_ccdc_archive 'CCDC 2057612'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2021-01-20 deposited with the CCDC.	2021-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
2-(isopropylthio)-4-(4-methoxyphenyl)pyridine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 N O S'
_chemical_formula_sum            'C15 H17 N O S'
_chemical_formula_weight         259.35

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.8398(4)
_cell_length_b                   22.2474(13)
_cell_length_c                   7.0250(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.163(6)
_cell_angle_gamma                90
_cell_volume                     1333.46(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3474
_cell_measurement_theta_min      2.5190
_cell_measurement_theta_max      29.7000

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.230
_shelx_estimated_absorpt_T_min   0.914
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.62885
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            23262
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.387
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3298
_reflns_number_gt                2627
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0546P)²+0.5470P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3298
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1248
_refine_ls_wR_factor_gt          0.1161
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.19170(6) 0.04714(2) 0.64088(8) 0.02812(15) Uani 1 1 d . . . . .
C5 C 0.0414(2) 0.19553(9) 0.8261(3) 0.0249(4) Uani 1 1 d . . . . .
H5 H 0.0361(2) 0.2277(8) 0.915(2) 0.030 Uiso 1 1 calc R U . . .
N1 N -0.06355(18) 0.15059(7) 0.8073(2) 0.0248(3) Uani 1 1 d . . . . .
C6 C -0.2972(2) 0.06065(9) 0.8285(3) 0.0251(4) Uani 1 1 d . . . . .
H6 H -0.3108(4) 0.1033(10) 0.8387(4) 0.030 Uiso 1 1 calc R U . . .
C9 C 0.2847(2) 0.15385(8) 0.4789(3) 0.0211(4) Uani 1 1 d . . . . .
C3 C 0.1674(2) 0.15183(8) 0.5963(3) 0.0216(4) Uani 1 1 d . . . . .
C11 C 0.5415(2) 0.18228(9) 0.4446(3) 0.0266(4) Uani 1 1 d . . . . .
H11 H 0.640(2) 0.1987(4) 0.4990(13) 0.032 Uiso 1 1 calc R U . . .
C4 C 0.1564(2) 0.19833(8) 0.7255(3) 0.0233(4) Uani 1 1 d . . . . .
H4 H 0.2310(17) 0.2334(8) 0.7452(5) 0.028 Uiso 1 1 calc R U . . .
C10 C 0.4327(2) 0.17918(8) 0.5548(3) 0.0246(4) Uani 1 1 d . . . . .
H10 H 0.4602(7) 0.1951(4) 0.689(3) 0.030 Uiso 1 1 calc R U . . .
C14 C 0.2486(2) 0.13124(8) 0.2858(3) 0.0238(4) Uani 1 1 d . . . . .
H14 H 0.146(2) 0.1126(4) 0.2299(13) 0.029 Uiso 1 1 calc R U . . .
C13 C 0.3551(2) 0.13485(9) 0.1727(3) 0.0247(4) Uani 1 1 d . . . . .
H13 H 0.3274(7) 0.1194(4) 0.038(3) 0.030 Uiso 1 1 calc R U . . .
C2 C 0.0626(2) 0.10406(8) 0.5792(3) 0.0227(4) Uani 1 1 d . . . . .
H2 H 0.0688(2) 0.0700(8) 0.495(2) 0.027 Uiso 1 1 calc R U . . .
C8 C -0.4588(2) 0.03188(10) 0.7577(3) 0.0304(4) Uani 1 1 d . . . . .
H8A H -0.4472(3) -0.0117(6) 0.744(2) 0.046 Uiso 1 1 calc R U . . .
H8B H -0.5141(11) 0.0491(5) 0.629(2) 0.046 Uiso 1 1 calc R U . . .
H8C H -0.5194(11) 0.0397(6) 0.8543(17) 0.046 Uiso 1 1 calc R U . . .
C12 C 0.5023(2) 0.16071(8) 0.2517(3) 0.0242(4) Uani 1 1 d . . . . .
C15 C 0.7520(2) 0.18669(10) 0.2045(3) 0.0326(5) Uani 1 1 d . . . . .
H15A H 0.7443(2) 0.2285(6) 0.245(2) 0.049 Uiso 1 1 calc R U . . .
H15B H 0.8097(10) 0.1852(6) 0.1027(16) 0.049 Uiso 1 1 calc R U . . .
H15C H 0.8076(10) 0.1628(5) 0.319(2) 0.049 Uiso 1 1 calc R U . . .
C1 C -0.0517(2) 0.10594(8) 0.6847(3) 0.0233(4) Uani 1 1 d . . . . .
O1 O 0.59804(15) 0.16275(6) 0.1269(2) 0.0295(3) Uani 1 1 d . . . . .
C7 C -0.2056(2) 0.03735(10) 1.0291(3) 0.0320(5) Uani 1 1 d . . . . .
H7A H -0.2631(12) 0.0470(6) 1.1287(15) 0.048 Uiso 1 1 calc R U . . .
H7B H -0.1011(17) 0.0566(6) 1.0668(12) 0.048 Uiso 1 1 calc R U . . .
H7C H -0.1929(15) -0.0067(7) 1.0225(7) 0.048 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.7714(19) . ?
S1 C6 1.827(2) . ?
C5 N1 1.347(2) . ?
C5 C4 1.383(3) . ?
C5 H5 0.96(2) . ?
N1 C1 1.337(2) . ?
C6 C7 1.522(3) . ?
C6 C8 1.525(3) . ?
C6 H6 0.96(2) . ?
C9 C10 1.396(2) . ?
C9 C14 1.403(3) . ?
C9 C3 1.485(3) . ?
C3 C2 1.394(3) . ?
C3 C4 1.397(3) . ?
C11 C10 1.385(3) . ?
C11 C12 1.393(3) . ?
C11 H11 0.93(2) . ?
C4 H4 1.01(2) . ?
C10 H10 0.97(2) . ?
C14 C13 1.384(3) . ?
C14 H14 0.98(2) . ?
C13 C12 1.398(3) . ?
C13 H13 0.98(2) . ?
C2 C1 1.402(3) . ?
C2 H2 0.97(2) . ?
C8 H8A 0.983(14) . ?
C8 H8B 0.983(14) . ?
C8 H8C 0.983(14) . ?
C12 O1 1.369(2) . ?
C15 O1 1.430(2) . ?
C15 H15A 0.981(13) . ?
C15 H15B 0.981(13) . ?
C15 H15C 0.981(13) . ?
C7 H7A 0.990(14) . ?
C7 H7B 0.990(14) . ?
C7 H7C 0.990(14) . ?

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
C1 S1 C6 102.60(9) . . ?
N1 C5 C4 124.27(18) . . ?
N1 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
C1 N1 C5 116.53(17) . . ?
C7 C6 C8 112.65(17) . . ?
C7 C6 S1 111.33(13) . . ?
C8 C6 S1 107.89(14) . . ?
C7 C6 H6 108.3 . . ?
C8 C6 H6 108.3 . . ?
S1 C6 H6 108.3 . . ?
C10 C9 C14 117.88(17) . . ?
C10 C9 C3 121.38(17) . . ?
C14 C9 C3 120.73(16) . . ?
C2 C3 C4 117.54(17) . . ?
C2 C3 C9 121.35(17) . . ?
C4 C3 C9 121.09(16) . . ?
C10 C11 C12 119.63(17) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C5 C4 C3 118.99(17) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C11 C10 C9 121.64(18) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C13 C14 C9 121.17(17) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
C14 C13 C12 119.88(18) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C3 C2 C1 119.13(17) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C12 C11 124.97(17) . . ?
O1 C12 C13 115.25(17) . . ?
C11 C12 C13 119.78(18) . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C1 C2 123.48(17) . . ?
N1 C1 S1 119.48(14) . . ?
C2 C1 S1 116.97(14) . . ?
C12 O1 C15 117.01(16) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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
C4 C5 N1 C1 1.0(3) . . . . ?
C1 S1 C6 C7 -79.41(15) . . . . ?
C1 S1 C6 C8 156.50(13) . . . . ?
C10 C9 C3 C2 -146.06(18) . . . . ?
C14 C9 C3 C2 35.2(3) . . . . ?
C10 C9 C3 C4 35.0(3) . . . . ?
C14 C9 C3 C4 -143.71(18) . . . . ?
N1 C5 C4 C3 -0.5(3) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
C9 C3 C4 C5 177.58(16) . . . . ?
C12 C11 C10 C9 1.2(3) . . . . ?
C14 C9 C10 C11 0.1(3) . . . . ?
C3 C9 C10 C11 -178.69(17) . . . . ?
C10 C9 C14 C13 -1.1(3) . . . . ?
C3 C9 C14 C13 177.68(17) . . . . ?
C9 C14 C13 C12 0.8(3) . . . . ?
C4 C3 C2 C1 2.6(3) . . . . ?
C9 C3 C2 C1 -176.34(16) . . . . ?
C10 C11 C12 O1 178.21(18) . . . . ?
C10 C11 C12 C13 -1.5(3) . . . . ?
C14 C13 C12 O1 -179.22(17) . . . . ?
C14 C13 C12 C11 0.5(3) . . . . ?
C5 N1 C1 C2 0.4(3) . . . . ?
C5 N1 C1 S1 -176.53(14) . . . . ?
C3 C2 C1 N1 -2.2(3) . . . . ?
C3 C2 C1 S1 174.78(14) . . . . ?
C6 S1 C1 N1 -10.64(17) . . . . ?
C6 S1 C1 C2 172.27(14) . . . . ?
C11 C12 O1 C15 2.7(3) . . . . ?
C13 C12 O1 C15 -177.59(17) . . . . ?

_refine_diff_density_max         0.389
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.062

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_test1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2057613'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2021-01-20 deposited with the CCDC.	2021-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
3-iodo-2-(isopropylthio)-4-(4-methoxyphenyl)pyridine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H16 I N O S'
_chemical_formula_sum            'C15 H16 I N O S'
_chemical_formula_weight         385.25

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.5870(3)
_cell_length_b                   6.1553(2)
_cell_length_c                   14.6215(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.114(3)
_cell_angle_gamma                90
_cell_volume                     763.07(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    7033
_cell_measurement_theta_min      2.4500
_cell_measurement_theta_max      31.9150

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    2.227
_shelx_estimated_absorpt_T_min   0.664
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85673
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            14968
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.402
_diffrn_reflns_theta_max         30.504
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4640
_reflns_number_gt                4430
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.843
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.994

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

_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0215P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1923 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.044(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4640
_refine_ls_number_parameters     185
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0225
_refine_ls_R_factor_gt           0.0206
_refine_ls_wR_factor_ref         0.0439
_refine_ls_wR_factor_gt          0.0430
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.58737(2) 0.85001(3) 0.62175(2) 0.02248(5) Uani 1 1 d . . . . .
S1 S 0.82154(9) 0.57177(12) 0.78440(5) 0.02102(14) Uani 1 1 d . . . . .
C7 C 0.8309(4) 0.1859(5) 0.8811(3) 0.0300(7) Uani 1 1 d . . . . .
H7A H 0.848(3) 0.112(2) 0.8267(17) 0.045 Uiso 1 1 calc R U . . .
H7B H 0.721(3) 0.2016(6) 0.8807(18) 0.045 Uiso 1 1 calc R U . . .
H7C H 0.876(2) 0.105(3) 0.9338(15) 0.045 Uiso 1 1 calc R U . . .
C9 C 0.3023(3) 1.0472(4) 0.7287(2) 0.0180(5) Uani 1 1 d . . . . .
C13 C 0.0358(3) 1.1200(5) 0.6515(2) 0.0202(6) Uani 1 1 d . . . . .
H13 H -0.062(4) 1.0771(19) 0.6356(7) 0.024 Uiso 1 1 calc R U . . .
C3 C 0.4151(3) 0.9034(4) 0.7880(2) 0.0176(6) Uani 1 1 d . . . . .
C2 C 0.3920(3) 0.8600(11) 0.87897(17) 0.0214(5) Uani 1 1 d . . . . .
H2 H 0.303(3) 0.921(2) 0.9025(9) 0.026 Uiso 1 1 calc R U . . .
C12 C 0.0834(3) 1.3254(9) 0.62359(18) 0.0209(8) Uani 1 1 d . . . . .
N1 N 0.6257(3) 0.6391(4) 0.90709(18) 0.0220(5) Uani 1 1 d . . . . .
O1 O -0.0129(2) 1.4680(3) 0.57153(16) 0.0245(5) Uani 1 1 d . . . . .
C14 C 0.1452(3) 0.9855(5) 0.7044(2) 0.0194(5) Uani 1 1 d . . . . .
H14 H 0.1141(16) 0.857(6) 0.7232(9) 0.023 Uiso 1 1 calc R U . . .
C4 C 0.5471(3) 0.8095(4) 0.75918(19) 0.0175(6) Uani 1 1 d . . . . .
C10 C 0.3488(3) 1.2513(5) 0.7005(2) 0.0212(6) Uani 1 1 d . . . . .
H10 H 0.465(4) 1.3004(16) 0.7185(6) 0.025 Uiso 1 1 calc R U . . .
C6 C 0.9074(3) 0.4089(5) 0.8845(2) 0.0188(6) Uani 1 1 d . . . . .
H6 H 0.8885(8) 0.485(3) 0.942(2) 0.023 Uiso 1 1 calc R U . . .
C5 C 0.6503(3) 0.6792(4) 0.8207(2) 0.0175(5) Uani 1 1 d . . . . .
C1 C 0.4979(4) 0.7284(5) 0.9346(2) 0.0241(6) Uani 1 1 d . . . . .
H1 H 0.4792(9) 0.6993(14) 0.996(3) 0.029 Uiso 1 1 calc R U . . .
C15 C -0.1697(3) 1.3948(5) 0.5361(2) 0.0239(7) Uani 1 1 d . . . . .
H15A H -0.1642(3) 1.262(3) 0.5013(19) 0.036 Uiso 1 1 calc R U . . .
H15B H -0.2241(17) 1.505(3) 0.4960(16) 0.036 Uiso 1 1 calc R U . . .
H15C H -0.2264(15) 1.368(4) 0.5870(11) 0.036 Uiso 1 1 calc R U . . .
C11 C 0.2412(4) 1.3875(5) 0.6489(2) 0.0233(7) Uani 1 1 d . . . . .
H11 H 0.2753(14) 1.528(5) 0.6299(8) 0.028 Uiso 1 1 calc R U . . .
C8 C 1.0848(4) 0.3970(5) 0.8841(2) 0.0279(8) Uani 1 1 d . . . . .
H8A H 1.1313(12) 0.317(4) 0.9337(15) 0.042 Uiso 1 1 calc R U . . .
H8B H 1.1262(11) 0.534(3) 0.8879(18) 0.042 Uiso 1 1 calc R U . . .
H8C H 1.1034(6) 0.333(4) 0.8304(14) 0.042 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C4 2.107(3) . ?
S1 C5 1.769(3) . ?
S1 C6 1.830(3) . ?
C7 C6 1.520(4) . ?
C7 H7A 0.95(2) . ?
C7 H7B 0.95(2) . ?
C7 H7C 0.95(2) . ?
C9 C14 1.393(4) . ?
C9 C10 1.400(4) . ?
C9 C3 1.486(4) . ?
C13 C14 1.391(4) . ?
C13 C12 1.409(6) . ?
C13 H13 0.88(4) . ?
C3 C4 1.395(4) . ?
C3 C2 1.401(4) . ?
C2 C1 1.382(5) . ?
C2 H2 0.96(4) . ?
C12 O1 1.354(5) . ?
C12 C11 1.401(4) . ?
N1 C5 1.336(4) . ?
N1 C1 1.344(4) . ?
O1 C15 1.437(3) . ?
C14 H14 0.89(4) . ?
C4 C5 1.409(4) . ?
C10 C11 1.380(4) . ?
C10 H10 1.03(3) . ?
C6 C8 1.526(4) . ?
C6 H6 1.00(4) . ?
C1 H1 0.95(4) . ?
C15 H15A 0.967(19) . ?
C15 H15B 0.967(19) . ?
C15 H15C 0.967(19) . ?
C11 H11 0.97(4) . ?
C8 H8A 0.92(2) . ?
C8 H8B 0.92(2) . ?
C8 H8C 0.92(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
C5 S1 C6 102.32(13) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 C9 C10 118.7(3) . . ?
C14 C9 C3 120.1(3) . . ?
C10 C9 C3 121.1(3) . . ?
C14 C13 C12 119.6(3) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C4 C3 C2 116.9(3) . . ?
C4 C3 C9 123.8(3) . . ?
C2 C3 C9 119.3(3) . . ?
C1 C2 C3 119.4(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
O1 C12 C11 116.8(4) . . ?
O1 C12 C13 124.5(3) . . ?
C11 C12 C13 118.8(3) . . ?
C5 N1 C1 117.8(3) . . ?
C12 O1 C15 116.9(3) . . ?
C13 C14 C9 121.4(3) . . ?
C13 C14 H14 119.3 . . ?
C9 C14 H14 119.3 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 I1 120.2(2) . . ?
C5 C4 I1 119.64(19) . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C7 C6 C8 112.5(3) . . ?
C7 C6 S1 110.6(2) . . ?
C8 C6 S1 107.4(2) . . ?
C7 C6 H6 108.7 . . ?
C8 C6 H6 108.7 . . ?
S1 C6 H6 108.7 . . ?
N1 C5 C4 122.0(3) . . ?
N1 C5 S1 118.6(2) . . ?
C4 C5 S1 119.3(2) . . ?
N1 C1 C2 123.8(3) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C11 C12 120.9(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
C14 C9 C3 C4 117.4(3) . . . . ?
C10 C9 C3 C4 -66.2(4) . . . . ?
C14 C9 C3 C2 -63.8(4) . . . . ?
C10 C9 C3 C2 112.7(4) . . . . ?
C4 C3 C2 C1 -0.3(6) . . . . ?
C9 C3 C2 C1 -179.2(4) . . . . ?
C14 C13 C12 O1 179.5(3) . . . . ?
C14 C13 C12 C11 1.0(5) . . . . ?
C11 C12 O1 C15 172.7(3) . . . . ?
C13 C12 O1 C15 -5.8(4) . . . . ?
C12 C13 C14 C9 -1.6(5) . . . . ?
C10 C9 C14 C13 1.4(4) . . . . ?
C3 C9 C14 C13 177.9(3) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C9 C3 C4 C5 178.4(2) . . . . ?
C2 C3 C4 I1 176.8(3) . . . . ?
C9 C3 C4 I1 -4.3(3) . . . . ?
C14 C9 C10 C11 -0.6(5) . . . . ?
C3 C9 C10 C11 -177.1(3) . . . . ?
C5 S1 C6 C7 83.5(2) . . . . ?
C5 S1 C6 C8 -153.3(2) . . . . ?
C1 N1 C5 C4 -0.3(4) . . . . ?
C1 N1 C5 S1 177.7(2) . . . . ?
C3 C4 C5 N1 0.8(4) . . . . ?
I1 C4 C5 N1 -176.5(2) . . . . ?
C3 C4 C5 S1 -177.2(2) . . . . ?
I1 C4 C5 S1 5.5(3) . . . . ?
C6 S1 C5 N1 4.6(3) . . . . ?
C6 S1 C5 C4 -177.4(2) . . . . ?
C5 N1 C1 C2 -0.5(5) . . . . ?
C3 C2 C1 N1 0.8(7) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
O1 C12 C11 C10 -178.8(3) . . . . ?
C13 C12 C11 C10 -0.3(5) . . . . ?

_refine_diff_density_max         0.819
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.069

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_test1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2057614'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2021-01-20 deposited with the CCDC.	2021-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
2-ethoxy-4-(4-methoxyphenyl)-3-(trimethylsilyl)pyridine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H23 N O2 Si'
_chemical_formula_sum            'C17 H23 N O2 Si'
_chemical_formula_weight         301.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   30.9518(6)
_cell_length_b                   6.9485(2)
_cell_length_c                   15.9226(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3424.45(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    14903
_cell_measurement_theta_min      2.6130
_cell_measurement_theta_max      31.2940

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.449
_exptl_crystal_size_mid          0.409
_exptl_crystal_size_min          0.292
_exptl_absorpt_coefficient_mu    0.141
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84311
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            65322
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.558
_diffrn_reflns_theta_max         30.504
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             10423
_reflns_number_gt                8971
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.937
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.996

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

_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0497P)²+0.5858P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3866 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         10423
_refine_ls_number_parameters     413
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.0995
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.23768(2) 0.82774(9) 0.91055(4) 0.02251(13) Uani 1 1 d . . . . .
Si2 Si 0.01665(2) 0.67257(9) 0.65232(4) 0.02625(14) Uani 1 1 d . . . . .
O1 O 0.16557(5) 0.5710(2) 0.87389(10) 0.0249(3) Uani 1 1 d . . . . .
N1 N 0.16693(6) 0.5396(3) 0.73035(12) 0.0254(4) Uani 1 1 d . . . . .
N2 N 0.08326(6) 0.9665(3) 0.83697(12) 0.0253(4) Uani 1 1 d . . . . .
C14 C 0.31971(7) 1.2896(4) 0.68863(15) 0.0244(4) Uani 1 1 d . . . . .
C20 C 0.01863(7) 0.6843(3) 0.83801(14) 0.0220(4) Uani 1 1 d . . . . .
C12 C 0.25065(7) 1.1668(3) 0.73298(16) 0.0257(4) Uani 1 1 d . . . . .
H12 H 0.2224(9) 1.1890(8) 0.7545(7) 0.031 Uiso 1 1 calc R U . . .
O3 O 0.08724(5) 0.9365(2) 0.69372(10) 0.0277(4) Uani 1 1 d . . . . .
C22 C 0.06872(7) 0.8857(3) 0.76725(13) 0.0216(4) Uani 1 1 d . . . . .
O2 O 0.34424(6) 1.4511(3) 0.67873(12) 0.0330(4) Uani 1 1 d . . . . .
C2 C 0.21666(7) 0.7583(3) 0.80244(15) 0.0199(5) Uani 1 1 d . . . . .
C29 C 0.00091(8) 0.3353(3) 0.82950(17) 0.0305(5) Uani 1 1 d . . . . .
H29 H 0.0285(10) 0.3138(9) 0.8145(6) 0.037 Uiso 1 1 calc R U . . .
C21 C 0.03523(7) 0.7463(3) 0.76103(16) 0.0214(5) Uani 1 1 d . . . . .
C4 C 0.21619(8) 0.7333(3) 0.65098(17) 0.0255(5) Uani 1 1 d . . . . .
H4 H 0.2270(4) 0.7694(13) 0.5982(19) 0.031 Uiso 1 1 calc R U . . .
C3 C 0.23225(7) 0.8184(3) 0.72439(14) 0.0207(4) Uani 1 1 d . . . . .
C19 C 0.03342(8) 0.7692(3) 0.91290(17) 0.0262(5) Uani 1 1 d . . . . .
H19 H 0.0215(4) 0.7295(14) 0.9669(19) 0.031 Uiso 1 1 calc R U . . .
C1 C 0.18289(7) 0.6203(3) 0.79887(13) 0.0210(4) Uani 1 1 d . . . . .
O4 O -0.09474(6) 0.0513(3) 0.86679(15) 0.0425(5) Uani 1 1 d . . . . .
C16 C 0.30516(7) 0.9500(3) 0.68289(15) 0.0252(4) Uani 1 1 d . . . . .
H16 H 0.3148(3) 0.817(4) 0.6688(4) 0.030 Uiso 1 1 calc R U . . .
C7 C 0.11635(8) 0.4130(4) 0.96382(16) 0.0299(5) Uani 1 1 d . . . . .
H7A H 0.1397(5) 0.359(3) 0.9960(7) 0.045 Uiso 1 1 calc R U . . .
H7B H 0.0918(6) 0.328(3) 0.9665(2) 0.045 Uiso 1 1 calc R U . . .
H7C H 0.1086(6) 0.537(2) 0.9864(6) 0.045 Uiso 1 1 calc R U . . .
C15 C 0.33329(8) 1.1034(4) 0.67074(15) 0.0267(5) Uani 1 1 d . . . . .
H15 H 0.3612(9) 1.0814(8) 0.6506(7) 0.032 Uiso 1 1 calc R U . . .
C18 C 0.06474(8) 0.9081(3) 0.90920(15) 0.0280(4) Uani 1 1 d . . . . .
H18 H 0.0744(3) 0.9695(19) 0.9630(17) 0.034 Uiso 1 1 calc R U . . .
C32 C -0.08425(8) 0.3988(4) 0.87532(16) 0.0307(5) Uani 1 1 d . . . . .
H32 H -0.1124(10) 0.4206(9) 0.8896(5) 0.037 Uiso 1 1 calc R U . . .
C11 C 0.26375(7) 0.9791(3) 0.71439(13) 0.0202(4) Uani 1 1 d . . . . .
C31 C -0.06984(8) 0.2137(4) 0.86071(17) 0.0299(5) Uani 1 1 d . . . . .
C28 C -0.01279(7) 0.5229(3) 0.84475(14) 0.0230(4) Uani 1 1 d . . . . .
C24 C 0.13754(9) 1.0979(4) 0.60701(17) 0.0341(5) Uani 1 1 d . . . . .
H24A H 0.1459(6) 0.976(2) 0.5850(6) 0.051 Uiso 1 1 calc R U . . .
H24B H 0.1617(6) 1.183(3) 0.6059(2) 0.051 Uiso 1 1 calc R U . . .
H24C H 0.1147(5) 1.150(3) 0.5736(7) 0.051 Uiso 1 1 calc R U . . .
C13 C 0.27831(8) 1.3206(3) 0.72045(16) 0.0277(5) Uani 1 1 d . . . . .
H13 H 0.2689(3) 1.450(4) 0.7338(5) 0.033 Uiso 1 1 calc R U . . .
C6 C 0.13024(7) 0.4358(3) 0.87404(15) 0.0246(4) Uani 1 1 d . . . . .
H6A H 0.1393(2) 0.316(3) 0.8518(5) 0.029 Uiso 1 1 calc R U . . .
H6B H 0.1071(5) 0.4828(10) 0.8411(7) 0.029 Uiso 1 1 calc R U . . .
C33 C -0.05550(8) 0.5518(4) 0.86817(16) 0.0301(5) Uani 1 1 d . . . . .
H33 H -0.0649(3) 0.673(4) 0.8791(4) 0.036 Uiso 1 1 calc R U . . .
C30 C -0.02701(9) 0.1823(4) 0.83692(19) 0.0347(6) Uani 1 1 d . . . . .
H30 H -0.0169(4) 0.051(5) 0.8255(5) 0.042 Uiso 1 1 calc R U . . .
C23 C 0.12217(7) 1.0739(4) 0.69622(15) 0.0280(5) Uani 1 1 d . . . . .
H23A H 0.1455(5) 1.0266(11) 0.7317(8) 0.034 Uiso 1 1 calc R U . . .
H23B H 0.1121(2) 1.196(3) 0.7186(5) 0.034 Uiso 1 1 calc R U . . .
C10 C 0.29093(8) 0.9551(4) 0.90600(18) 0.0379(6) Uani 1 1 d . . . . .
H10A H 0.28685(15) 1.081(3) 0.8850(14) 0.057 Uiso 1 1 calc R U . . .
H10B H 0.3099(4) 0.887(2) 0.8703(13) 0.057 Uiso 1 1 calc R U . . .
H10C H 0.3029(4) 0.962(3) 0.9604(11) 0.057 Uiso 1 1 calc R U . . .
C5 C 0.18426(8) 0.5959(4) 0.65723(16) 0.0281(5) Uani 1 1 d . . . . .
H5 H 0.1739(4) 0.538(2) 0.6068(17) 0.034 Uiso 1 1 calc R U . . .
C8 C 0.19746(10) 0.9866(5) 0.96349(19) 0.0420(7) Uani 1 1 d . . . . .
H8A H 0.1698(6) 0.932(2) 0.9586(13) 0.063 Uiso 1 1 calc R U . . .
H8B H 0.1977(5) 1.109(3) 0.9380(11) 0.063 Uiso 1 1 calc R U . . .
H8C H 0.2047(5) 0.999(3) 1.0205(12) 0.063 Uiso 1 1 calc R U . . .
C17 C 0.38705(9) 1.4275(4) 0.6481(2) 0.0412(6) Uani 1 1 d . . . . .
H17A H 0.4032(4) 1.347(3) 0.6862(12) 0.062 Uiso 1 1 calc R U . . .
H17B H 0.4009(4) 1.552(3) 0.6439(14) 0.062 Uiso 1 1 calc R U . . .
H17C H 0.38616(9) 1.368(3) 0.5933(13) 0.062 Uiso 1 1 calc R U . . .
C26 C 0.00798(11) 0.8921(5) 0.58632(19) 0.0469(7) Uani 1 1 d . . . . .
H26A H 0.0356(6) 0.943(2) 0.5687(13) 0.070 Uiso 1 1 calc R U . . .
H26B H -0.0072(8) 0.988(3) 0.6187(9) 0.070 Uiso 1 1 calc R U . . .
H26C H -0.0089(7) 0.8586(11) 0.5374(14) 0.070 Uiso 1 1 calc R U . . .
C9 C 0.24773(9) 0.6048(4) 0.97290(17) 0.0350(6) Uani 1 1 d . . . . .
H9A H 0.2643(6) 0.517(2) 0.9405(8) 0.053 Uiso 1 1 calc R U . . .
H9B H 0.2210(5) 0.547(2) 0.9873(11) 0.053 Uiso 1 1 calc R U . . .
H9C H 0.2630(6) 0.6366(8) 1.0225(11) 0.053 Uiso 1 1 calc R U . . .
C34 C -0.13851(9) 0.0759(5) 0.8906(2) 0.0438(7) Uani 1 1 d . . . . .
H34A H -0.13983(10) 0.140(3) 0.9449(13) 0.066 Uiso 1 1 calc R U . . .
H34B H -0.1524(4) -0.049(3) 0.8945(14) 0.066 Uiso 1 1 calc R U . . .
H34C H -0.1533(4) 0.154(3) 0.8489(12) 0.066 Uiso 1 1 calc R U . . .
C25 C 0.05770(11) 0.5098(6) 0.6060(2) 0.0547(9) Uani 1 1 d . . . . .
H25A H 0.0580(6) 0.382(3) 0.6384(13) 0.082 Uiso 1 1 calc R U . . .
H25B H 0.0876(7) 0.573(2) 0.6098(15) 0.082 Uiso 1 1 calc R U . . .
H25C H 0.0502(5) 0.484(3) 0.5442(15) 0.082 Uiso 1 1 calc R U . . .
C27 C -0.03673(9) 0.5459(5) 0.6529(2) 0.0461(7) Uani 1 1 d . . . . .
H27A H -0.0457(4) 0.525(3) 0.5983(12) 0.069 Uiso 1 1 calc R U . . .
H27B H -0.0569(5) 0.621(2) 0.6806(14) 0.069 Uiso 1 1 calc R U . . .
H27C H -0.0340(2) 0.429(3) 0.6801(14) 0.069 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si1 C8 1.865(3) . ?
Si1 C9 1.866(3) . ?
Si1 C10 1.872(3) . ?
Si1 C2 1.903(3) . ?
Si2 C25 1.854(3) . ?
Si2 C26 1.872(3) . ?
Si2 C27 1.872(3) . ?
Si2 C21 1.895(3) . ?
O1 C1 1.353(3) . ?
O1 C6 1.442(3) . ?
N1 C1 1.322(3) . ?
N1 C5 1.340(3) . ?
N2 C22 1.323(3) . ?
N2 C18 1.347(3) . ?
C14 O2 1.364(3) . ?
C14 C15 1.390(4) . ?
C14 C13 1.395(3) . ?
C20 C21 1.397(3) . ?
C20 C19 1.407(4) . ?
C20 C28 1.488(3) . ?
C12 C13 1.384(3) . ?
C12 C11 1.397(3) . ?
C12 H12 0.95(3) . ?
O3 C22 1.351(3) . ?
O3 C23 1.443(3) . ?
C22 C21 1.422(3) . ?
O2 C17 1.422(3) . ?
C2 C3 1.397(3) . ?
C2 C1 1.420(3) . ?
C29 C30 1.375(4) . ?
C29 C28 1.392(3) . ?
C29 H29 0.90(3) . ?
C4 C5 1.378(3) . ?
C4 C3 1.401(4) . ?
C4 H4 0.94(3) . ?
C3 C11 1.491(3) . ?
C19 C18 1.370(3) . ?
C19 H19 0.98(3) . ?
O4 C31 1.370(3) . ?
O4 C34 1.417(4) . ?
C16 C15 1.390(3) . ?
C16 C11 1.391(3) . ?
C16 H16 1.00(3) . ?
C7 C6 1.501(3) . ?
C7 H7A 0.961(18) . ?
C7 H7B 0.961(18) . ?
C7 H7C 0.961(18) . ?
C15 H15 0.94(3) . ?
C18 H18 1.00(3) . ?
C32 C31 1.381(4) . ?
C32 C33 1.391(4) . ?
C32 H32 0.91(3) . ?
C31 C30 1.396(4) . ?
C28 C33 1.388(3) . ?
C24 C23 1.507(3) . ?
C24 H24A 0.955(18) . ?
C24 H24B 0.955(19) . ?
C24 H24C 0.955(18) . ?
C13 H13 0.97(3) . ?
C6 H6A 0.95(2) . ?
C6 H6B 0.95(2) . ?
C33 H33 0.91(3) . ?
C30 H30 0.98(3) . ?
C23 H23A 0.97(2) . ?
C23 H23B 0.97(2) . ?
C10 H10A 0.943(19) . ?
C10 H10B 0.943(19) . ?
C10 H10C 0.943(19) . ?
C5 H5 0.95(3) . ?
C8 H8A 0.94(2) . ?
C8 H8B 0.94(2) . ?
C8 H8C 0.94(2) . ?
C17 H17A 0.97(2) . ?
C17 H17B 0.97(2) . ?
C17 H17C 0.97(2) . ?
C26 H26A 0.97(2) . ?
C26 H26B 0.97(2) . ?
C26 H26C 0.97(2) . ?
C9 H9A 0.947(18) . ?
C9 H9B 0.947(18) . ?
C9 H9C 0.947(18) . ?
C34 H34A 0.97(2) . ?
C34 H34B 0.97(2) . ?
C34 H34C 0.97(2) . ?
C25 H25A 1.03(2) . ?
C25 H25B 1.03(2) . ?
C25 H25C 1.03(2) . ?
C27 H27A 0.92(2) . ?
C27 H27B 0.92(2) . ?
C27 H27C 0.92(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
C8 Si1 C9 111.23(14) . . ?
C8 Si1 C10 108.99(14) . . ?
C9 Si1 C10 105.44(12) . . ?
C8 Si1 C2 109.32(12) . . ?
C9 Si1 C2 109.13(12) . . ?
C10 Si1 C2 112.71(12) . . ?
C25 Si2 C26 111.85(18) . . ?
C25 Si2 C27 108.65(17) . . ?
C26 Si2 C27 105.04(14) . . ?
C25 Si2 C21 108.68(12) . . ?
C26 Si2 C21 109.65(13) . . ?
C27 Si2 C21 112.98(13) . . ?
C1 O1 C6 117.82(17) . . ?
C1 N1 C5 116.34(19) . . ?
C22 N2 C18 116.3(2) . . ?
O2 C14 C15 125.0(2) . . ?
O2 C14 C13 115.2(2) . . ?
C15 C14 C13 119.7(2) . . ?
C21 C20 C19 119.7(2) . . ?
C21 C20 C28 122.4(2) . . ?
C19 C20 C28 117.9(2) . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C22 O3 C23 117.85(18) . . ?
N2 C22 O3 118.2(2) . . ?
N2 C22 C21 126.6(2) . . ?
O3 C22 C21 115.28(19) . . ?
C14 O2 C17 117.6(2) . . ?
C3 C2 C1 114.9(2) . . ?
C3 C2 Si1 127.64(17) . . ?
C1 C2 Si1 117.35(17) . . ?
C30 C29 C28 121.2(2) . . ?
C30 C29 H29 119.4 . . ?
C28 C29 H29 119.4 . . ?
C20 C21 C22 114.6(2) . . ?
C20 C21 Si2 127.35(17) . . ?
C22 C21 Si2 117.96(18) . . ?
C5 C4 C3 119.1(2) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C2 C3 C4 119.5(2) . . ?
C2 C3 C11 123.0(2) . . ?
C4 C3 C11 117.3(2) . . ?
C18 C19 C20 119.3(2) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
N1 C1 O1 118.25(19) . . ?
N1 C1 C2 126.5(2) . . ?
O1 C1 C2 115.3(2) . . ?
C31 O4 C34 117.2(2) . . ?
C15 C16 C11 121.0(2) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C16 C15 C14 119.7(2) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
N2 C18 C19 123.4(2) . . ?
N2 C18 H18 118.3 . . ?
C19 C18 H18 118.3 . . ?
C31 C32 C33 119.4(2) . . ?
C31 C32 H32 120.3 . . ?
C33 C32 H32 120.3 . . ?
C16 C11 C12 118.7(2) . . ?
C16 C11 C3 122.14(19) . . ?
C12 C11 C3 119.11(18) . . ?
O4 C31 C32 125.0(2) . . ?
O4 C31 C30 115.1(2) . . ?
C32 C31 C30 119.9(2) . . ?
C33 C28 C29 118.2(2) . . ?
C33 C28 C20 122.2(2) . . ?
C29 C28 C20 119.60(19) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
O1 C6 C7 106.72(18) . . ?
O1 C6 H6A 110.4 . . ?
C7 C6 H6A 110.4 . . ?
O1 C6 H6B 110.4 . . ?
C7 C6 H6B 110.4 . . ?
H6A C6 H6B 108.6 . . ?
C28 C33 C32 121.4(2) . . ?
C28 C33 H33 119.3 . . ?
C32 C33 H33 119.3 . . ?
C29 C30 C31 119.9(2) . . ?
C29 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?
O3 C23 C24 106.48(19) . . ?
O3 C23 H23A 110.4 . . ?
C24 C23 H23A 110.4 . . ?
O3 C23 H23B 110.4 . . ?
C24 C23 H23B 110.4 . . ?
H23A C23 H23B 108.6 . . ?
Si1 C10 H10A 109.5 . . ?
Si1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
Si1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C5 C4 123.5(2) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
Si1 C8 H8A 109.5 . . ?
Si1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Si1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
Si2 C26 H26A 109.5 . . ?
Si2 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
Si2 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
Si1 C9 H9A 109.5 . . ?
Si1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
Si1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O4 C34 H34A 109.5 . . ?
O4 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O4 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
Si2 C25 H25A 109.5 . . ?
Si2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
Si2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
Si2 C27 H27A 109.5 . . ?
Si2 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
Si2 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C18 N2 C22 O3 -178.3(2) . . . . ?
C18 N2 C22 C21 1.0(3) . . . . ?
C23 O3 C22 N2 0.9(3) . . . . ?
C23 O3 C22 C21 -178.47(18) . . . . ?
C15 C14 O2 C17 -0.2(4) . . . . ?
C13 C14 O2 C17 178.8(2) . . . . ?
C19 C20 C21 C22 4.0(3) . . . . ?
C28 C20 C21 C22 -172.62(19) . . . . ?
C19 C20 C21 Si2 -173.45(17) . . . . ?
C28 C20 C21 Si2 9.9(3) . . . . ?
N2 C22 C21 C20 -3.9(3) . . . . ?
O3 C22 C21 C20 175.37(19) . . . . ?
N2 C22 C21 Si2 173.80(18) . . . . ?
O3 C22 C21 Si2 -6.9(3) . . . . ?
C25 Si2 C21 C20 -106.9(2) . . . . ?
C26 Si2 C21 C20 130.6(2) . . . . ?
C27 Si2 C21 C20 13.8(2) . . . . ?
C25 Si2 C21 C22 75.7(2) . . . . ?
C26 Si2 C21 C22 -46.8(2) . . . . ?
C27 Si2 C21 C22 -163.60(18) . . . . ?
C1 C2 C3 C4 -3.9(3) . . . . ?
Si1 C2 C3 C4 171.93(17) . . . . ?
C1 C2 C3 C11 172.34(19) . . . . ?
Si1 C2 C3 C11 -11.8(3) . . . . ?
C5 C4 C3 C2 2.1(3) . . . . ?
C5 C4 C3 C11 -174.4(2) . . . . ?
C21 C20 C19 C18 -1.7(3) . . . . ?
C28 C20 C19 C18 175.1(2) . . . . ?
C5 N1 C1 O1 178.4(2) . . . . ?
C5 N1 C1 C2 -0.7(3) . . . . ?
C6 O1 C1 N1 -1.0(3) . . . . ?
C6 O1 C1 C2 178.13(18) . . . . ?
C3 C2 C1 N1 3.4(3) . . . . ?
Si1 C2 C1 N1 -172.89(18) . . . . ?
C3 C2 C1 O1 -175.66(18) . . . . ?
Si1 C2 C1 O1 8.0(3) . . . . ?
C11 C16 C15 C14 -1.3(4) . . . . ?
O2 C14 C15 C16 -179.6(2) . . . . ?
C13 C14 C15 C16 1.5(4) . . . . ?
C22 N2 C18 C19 1.8(3) . . . . ?
C20 C19 C18 N2 -1.5(4) . . . . ?
C15 C16 C11 C12 0.6(3) . . . . ?
C15 C16 C11 C3 177.2(2) . . . . ?
C13 C12 C11 C16 -0.1(3) . . . . ?
C13 C12 C11 C3 -176.8(2) . . . . ?
C2 C3 C11 C16 115.5(2) . . . . ?
C4 C3 C11 C16 -68.2(3) . . . . ?
C2 C3 C11 C12 -68.0(3) . . . . ?
C4 C3 C11 C12 108.4(2) . . . . ?
C34 O4 C31 C32 -0.6(4) . . . . ?
C34 O4 C31 C30 -179.9(3) . . . . ?
C33 C32 C31 O4 179.1(2) . . . . ?
C33 C32 C31 C30 -1.6(4) . . . . ?
C30 C29 C28 C33 0.3(4) . . . . ?
C30 C29 C28 C20 178.6(2) . . . . ?
C21 C20 C28 C33 -111.0(3) . . . . ?
C19 C20 C28 C33 72.3(3) . . . . ?
C21 C20 C28 C29 70.8(3) . . . . ?
C19 C20 C28 C29 -105.9(3) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
O2 C14 C13 C12 180.0(2) . . . . ?
C15 C14 C13 C12 -1.0(4) . . . . ?
C1 O1 C6 C7 -177.91(19) . . . . ?
C29 C28 C33 C32 -0.8(4) . . . . ?
C20 C28 C33 C32 -179.1(2) . . . . ?
C31 C32 C33 C28 1.5(4) . . . . ?
C28 C29 C30 C31 -0.5(4) . . . . ?
O4 C31 C30 C29 -179.5(2) . . . . ?
C32 C31 C30 C29 1.1(4) . . . . ?
C22 O3 C23 C24 178.0(2) . . . . ?
C1 N1 C5 C4 -1.6(4) . . . . ?
C3 C4 C5 N1 0.9(4) . . . . ?

_refine_diff_density_max         0.341
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.046

_shelxl_version_number           2014-3



