# 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_test2
_database_code_depnum_ccdc_archive 'CCDC 2061336'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2021-02-05 deposited with the CCDC.	2021-05-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
2-(3,5-dichloro-2-iodo-6-(methylthio)phenyl)-2H-1,2,3-triazole
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6 Cl2 I N3 S'
_chemical_formula_sum            'C9 H6 Cl2 I N3 S'
_chemical_formula_weight         386.03

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_H-M_alt        'I b a 2'
_space_group_name_Hall           'I 2 -2c'

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

_cell_length_a                   29.5021(13)
_cell_length_b                   9.0794(3)
_cell_length_c                   9.4820(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2539.86(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    5777
_cell_measurement_theta_min      2.3180
_cell_measurement_theta_max      28.8740

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    2.019
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    3.082
_shelx_estimated_absorpt_T_min   0.372
_shelx_estimated_absorpt_T_max   0.861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.59505
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (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            15592
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.347
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             2462
_reflns_number_gt                2254
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_max     0.980
_reflns_Friedel_fraction_full    0.979

_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (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)+(0.0399P)²+5.4896P] 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 984 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2462
_refine_ls_number_parameters     149
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0757
_refine_ls_wR_factor_gt          0.0722
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
I1 I 0.58824(2) 0.47291(5) 0.56589(8) 0.02333(16) Uani 1 1 d . . . . .
S1 S 0.61090(8) 0.9776(2) 0.2064(2) 0.0281(5) Uani 1 1 d . . . . .
Cl1 Cl 0.70094(7) 0.4262(2) 0.4988(2) 0.0293(4) Uani 1 1 d . . . . .
N1 N 0.5373(2) 0.7157(9) 0.2809(7) 0.0305(17) Uani 1 1 d . . . . .
C1 C 0.6116(3) 0.7365(9) 0.3804(7) 0.0195(16) Uani 1 1 d . . . . .
N2 N 0.5643(2) 0.7586(7) 0.3859(6) 0.0214(14) Uani 1 1 d . . . . .
Cl2 Cl 0.71950(7) 0.9058(2) 0.1820(2) 0.0305(4) Uani 1 1 d . . . . .
C2 C 0.6302(3) 0.6119(8) 0.4472(7) 0.0200(16) Uani 1 1 d . . . . .
N3 N 0.5433(2) 0.8198(7) 0.4953(7) 0.0248(14) Uani 1 1 d . . . . .
C3 C 0.6759(3) 0.5853(8) 0.4310(8) 0.0222(16) Uani 1 1 d . . . . .
C4 C 0.7033(3) 0.6785(9) 0.3538(8) 0.0249(17) Uani 1 1 d . . . . .
H4 H 0.732(3) 0.661(2) 0.3465(11) 0.030 Uiso 1 1 calc R U . . .
C6 C 0.6385(3) 0.8332(10) 0.2995(8) 0.0218(19) Uani 1 1 d . . . . .
C5 C 0.6843(3) 0.8005(9) 0.2880(8) 0.0246(18) Uani 1 1 d . . . . .
C8 C 0.4971(3) 0.7556(10) 0.3256(15) 0.035(2) Uani 1 1 d . . . . .
H8 H 0.471(3) 0.7431(18) 0.277(6) 0.042 Uiso 1 1 calc R U . . .
C7 C 0.6367(3) 1.1378(12) 0.2837(11) 0.044(3) Uani 1 1 d . . . . .
H7A H 0.6361 1.1289 0.3867 0.065 Uiso 1 1 calc R U . . .
H7B H 0.6198 1.2259 0.2552 0.065 Uiso 1 1 calc R U . . .
H7C H 0.6681 1.1458 0.2514 0.065 Uiso 1 1 calc R U . . .
C9 C 0.5002(3) 0.8192(9) 0.4567(9) 0.0267(17) Uani 1 1 d . . . . .
H9 H 0.476(2) 0.855(4) 0.509(5) 0.032 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 C2 2.095(7) . ?
S1 C6 1.779(9) . ?
S1 C7 1.798(10) . ?
Cl1 C3 1.745(8) . ?
N1 C8 1.311(12) . ?
N1 N2 1.332(9) . ?
C1 C2 1.408(11) . ?
C1 C6 1.411(11) . ?
C1 N2 1.412(10) . ?
N2 N3 1.330(9) . ?
Cl2 C5 1.733(8) . ?
C2 C3 1.379(11) . ?
N3 C9 1.323(10) . ?
C3 C4 1.381(11) . ?
C4 C5 1.390(11) . ?
C4 H4 0.86(8) . ?
C6 C5 1.386(12) . ?
C8 C9 1.374(17) . ?
C8 H8 0.90(10) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 H9 0.92(9) . ?

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
C6 S1 C7 101.5(4) . . ?
C8 N1 N2 102.6(8) . . ?
C2 C1 C6 121.7(7) . . ?
C2 C1 N2 118.9(7) . . ?
C6 C1 N2 119.3(7) . . ?
N3 N2 N1 115.3(6) . . ?
N3 N2 C1 123.3(6) . . ?
N1 N2 C1 121.4(6) . . ?
C3 C2 C1 118.2(7) . . ?
C3 C2 I1 122.2(6) . . ?
C1 C2 I1 119.7(6) . . ?
C9 N3 N2 103.3(7) . . ?
C2 C3 C4 121.7(7) . . ?
C2 C3 Cl1 121.2(6) . . ?
C4 C3 Cl1 117.1(6) . . ?
C3 C4 C5 119.3(8) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C5 C6 C1 117.2(7) . . ?
C5 C6 S1 124.4(6) . . ?
C1 C6 S1 118.1(6) . . ?
C6 C5 C4 122.0(8) . . ?
C6 C5 Cl2 120.8(6) . . ?
C4 C5 Cl2 117.2(6) . . ?
N1 C8 C9 110.5(9) . . ?
N1 C8 H8 124.8 . . ?
C9 C8 H8 124.8 . . ?
S1 C7 H7A 109.5 . . ?
S1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
S1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C9 C8 108.3(8) . . ?
N3 C9 H9 125.8 . . ?
C8 C9 H9 125.8 . . ?

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
C8 N1 N2 N3 1.5(9) . . . . ?
C8 N1 N2 C1 -179.8(7) . . . . ?
C2 C1 N2 N3 82.3(9) . . . . ?
C6 C1 N2 N3 -102.5(8) . . . . ?
C2 C1 N2 N1 -96.3(9) . . . . ?
C6 C1 N2 N1 78.9(9) . . . . ?
C6 C1 C2 C3 -0.4(10) . . . . ?
N2 C1 C2 C3 174.7(6) . . . . ?
C6 C1 C2 I1 180.0(5) . . . . ?
N2 C1 C2 I1 -4.9(9) . . . . ?
N1 N2 N3 C9 -1.4(9) . . . . ?
C1 N2 N3 C9 179.9(7) . . . . ?
C1 C2 C3 C4 1.1(11) . . . . ?
I1 C2 C3 C4 -179.3(5) . . . . ?
C1 C2 C3 Cl1 -175.1(5) . . . . ?
I1 C2 C3 Cl1 4.5(9) . . . . ?
C2 C3 C4 C5 -1.5(11) . . . . ?
Cl1 C3 C4 C5 174.9(6) . . . . ?
C2 C1 C6 C5 0.1(11) . . . . ?
N2 C1 C6 C5 -175.0(6) . . . . ?
C2 C1 C6 S1 174.4(5) . . . . ?
N2 C1 C6 S1 -0.8(9) . . . . ?
C7 S1 C6 C5 -66.7(7) . . . . ?
C7 S1 C6 C1 119.5(7) . . . . ?
C1 C6 C5 C4 -0.5(11) . . . . ?
S1 C6 C5 C4 -174.3(6) . . . . ?
C1 C6 C5 Cl2 175.9(6) . . . . ?
S1 C6 C5 Cl2 2.1(10) . . . . ?
C3 C4 C5 C6 1.2(11) . . . . ?
C3 C4 C5 Cl2 -175.4(6) . . . . ?
N2 N1 C8 C9 -1.0(10) . . . . ?
N2 N3 C9 C8 0.7(9) . . . . ?
N1 C8 C9 N3 0.2(11) . . . . ?

_refine_diff_density_max         1.370
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.110

_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
_database_code_depnum_ccdc_archive 'CCDC 2061337'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2021-02-05 deposited with the CCDC.	2021-05-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
(4-bromo-2,5-dimethoxyphenyl)(5-(4-(trimethylsilyl)-1H-
1,2,3-triazol-1-yl)benzo[d][1,3]dioxol-4-yl)methanol
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H24 Br N3 O5 Si'
_chemical_formula_sum            'C21 H24 Br N3 O5 Si'
_chemical_formula_weight         506.43

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0355(4)
_cell_length_b                   11.4221(6)
_cell_length_c                   13.0590(5)
_cell_angle_alpha                105.984(4)
_cell_angle_beta                 104.098(4)
_cell_angle_gamma                96.492(4)
_cell_volume                     1096.48(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3471
_cell_measurement_theta_min      2.6860
_cell_measurement_theta_max      31.2820

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.968
_shelx_estimated_absorpt_T_min   0.546
_shelx_estimated_absorpt_T_max   0.908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.88729
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (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            22400
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.715
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6683
_reflns_number_gt                4584
_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 1.171.40.82a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (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)+(0.0426P)²+0.0145P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6683
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.0929
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
Br1 Br 0.01593(4) -0.08437(3) 0.25563(2) 0.03237(10) Uani 1 1 d . . . . .
O1 O 0.4008(2) 0.10350(16) 0.67200(13) 0.0230(4) Uani 1 1 d . . . . .
N1 N 0.5882(2) 0.34801(18) 0.92169(14) 0.0159(4) Uani 1 1 d . . . . .
C1 C 0.4654(3) 0.2575(2) 0.92168(18) 0.0182(5) Uani 1 1 d . . . . .
H1 H 0.3968(19) 0.1889(19) 0.8590(17) 0.022 Uiso 1 1 calc R U . . .
H3 H 0.328(4) 0.505(3) 0.753(3) 0.042(9) Uiso 1 1 d . . . . .
Si1 Si 0.30676(9) 0.20479(6) 1.09033(5) 0.01817(15) Uani 1 1 d . . . . .
N3 N 0.5811(3) 0.38931(19) 1.09027(15) 0.0197(4) Uani 1 1 d . . . . .
O3 O 0.2861(2) 0.45201(16) 0.68978(13) 0.0173(3) Uani 1 1 d . . . . .
C3 C 0.4057(3) 0.2588(3) 1.24381(19) 0.0246(6) Uani 1 1 d . . . . .
H3A H 0.415(2) 0.3507(14) 1.2732(5) 0.037 Uiso 1 1 calc R U . . .
H3B H 0.525(2) 0.2385(15) 1.2619(4) 0.037 Uiso 1 1 calc R U . . .
H3C H 0.3305(17) 0.2162(14) 1.2789(6) 0.037 Uiso 1 1 calc R U . . .
C2 C 0.4578(3) 0.2831(2) 1.02950(18) 0.0179(5) Uani 1 1 d . . . . .
O2 O -0.0477(2) 0.17529(17) 0.30945(13) 0.0289(4) Uani 1 1 d . . . . .
N2 N 0.6600(3) 0.42921(18) 1.02565(15) 0.0188(4) Uani 1 1 d . . . . .
O4 O 0.5454(2) 0.38789(17) 0.55076(12) 0.0218(4) Uani 1 1 d . . . . .
C4 C 0.2800(4) 0.0339(2) 1.0315(2) 0.0276(6) Uani 1 1 d . . . . .
H4A H 0.203(2) -0.0056(7) 1.0616(12) 0.041 Uiso 1 1 calc R U . . .
H4B H 0.3901(18) 0.0106(5) 1.0496(13) 0.041 Uiso 1 1 calc R U . . .
H4C H 0.233(2) 0.0097(5) 0.9532(13) 0.041 Uiso 1 1 calc R U . . .
C5 C 0.0921(3) 0.2516(3) 1.0553(2) 0.0277(6) Uani 1 1 d . . . . .
H5A H 0.0470(14) 0.2298(16) 0.9777(13) 0.042 Uiso 1 1 calc R U . . .
H5B H 0.1060(5) 0.3379(14) 1.0870(14) 0.042 Uiso 1 1 calc R U . . .
H5C H 0.0144(15) 0.2110(15) 1.0835(14) 0.042 Uiso 1 1 calc R U . . .
O5 O 0.8449(2) 0.42708(17) 0.58543(13) 0.0231(4) Uani 1 1 d . . . . .
C6 C 0.6549(3) 0.3665(2) 0.83311(17) 0.0159(5) Uani 1 1 d . . . . .
C7 C 0.8346(3) 0.3922(2) 0.85513(19) 0.0197(5) Uani 1 1 d . . . . .
H7 H 0.905(2) 0.3954(2) 0.925(2) 0.024 Uiso 1 1 calc R U . . .
C8 C 0.9146(3) 0.4134(2) 0.77673(19) 0.0210(5) Uani 1 1 d . . . . .
H8 H 1.035(4) 0.4313(6) 0.7916(5) 0.025 Uiso 1 1 calc R U . . .
C9 C 0.8033(3) 0.4059(2) 0.67601(18) 0.0172(5) Uani 1 1 d . . . . .
C10 C 0.6838(3) 0.3938(3) 0.5012(2) 0.0340(7) Uani 1 1 d . . . . .
H10A H 0.6766(4) 0.3136(17) 0.4479(12) 0.041 Uiso 1 1 calc R U . . .
H10B H 0.6747(4) 0.4549(13) 0.4621(9) 0.041 Uiso 1 1 calc R U . . .
C12 C 0.5399(3) 0.3605(2) 0.73006(17) 0.0142(4) Uani 1 1 d . . . . .
C11 C 0.6239(3) 0.3814(2) 0.65465(17) 0.0158(5) Uani 1 1 d . . . . .
C13 C 0.3407(3) 0.3404(2) 0.69942(17) 0.0158(5) Uani 1 1 d . . . . .
H13 H 0.3029(11) 0.3193(6) 0.7580(16) 0.019 Uiso 1 1 calc R U . . .
C17 C 0.1072(3) 0.0461(2) 0.39228(18) 0.0216(5) Uani 1 1 d . . . . .
C19 C 0.2897(3) 0.1173(2) 0.57977(18) 0.0183(5) Uani 1 1 d . . . . .
C16 C 0.0669(3) 0.1620(2) 0.40040(18) 0.0198(5) Uani 1 1 d . . . . .
C21 C -0.0557(4) 0.2979(3) 0.3069(2) 0.0275(6) Uani 1 1 d . . . . .
H21A H -0.094(2) 0.3411(9) 0.3672(13) 0.041 Uiso 1 1 calc R U . . .
H21B H -0.135(2) 0.2950(3) 0.2389(13) 0.041 Uiso 1 1 calc R U . . .
H21C H 0.0570(19) 0.3396(9) 0.3129(14) 0.041 Uiso 1 1 calc R U . . .
C20 C 0.4367(4) -0.0165(2) 0.6674(2) 0.0268(6) Uani 1 1 d . . . . .
H20A H 0.3270(18) -0.0741(10) 0.6554(14) 0.040 Uiso 1 1 calc R U . . .
H20B H 0.521(2) -0.0121(4) 0.7382(12) 0.040 Uiso 1 1 calc R U . . .
H20C H 0.487(2) -0.0470(9) 0.6053(13) 0.040 Uiso 1 1 calc R U . . .
C14 C 0.2553(3) 0.2362(2) 0.59051(17) 0.0154(5) Uani 1 1 d . . . . .
C15 C 0.1421(3) 0.2571(2) 0.50114(18) 0.0187(5) Uani 1 1 d . . . . .
H15 H 0.1162(8) 0.335(2) 0.5084(3) 0.022 Uiso 1 1 calc R U . . .
C18 C 0.2162(3) 0.0215(2) 0.48076(19) 0.0209(5) Uani 1 1 d . . . . .
H18 H 0.2381(8) -0.053(2) 0.4742(3) 0.025 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
Br1 C17 1.895(2) . ?
O1 C19 1.373(3) . ?
O1 C20 1.421(3) . ?
N1 C1 1.346(3) . ?
N1 N2 1.357(2) . ?
N1 C6 1.442(3) . ?
C1 C2 1.375(3) . ?
C1 H1 0.96(3) . ?
Si1 C5 1.852(3) . ?
Si1 C4 1.856(3) . ?
Si1 C3 1.861(2) . ?
Si1 C2 1.876(3) . ?
N3 N2 1.315(3) . ?
N3 C2 1.378(3) . ?
O3 C13 1.422(3) . ?
O3 H3 0.84(3) . ?
C3 H3A 1.001(15) . ?
C3 H3B 1.001(15) . ?
C3 H3C 1.001(15) . ?
O2 C16 1.371(3) . ?
O2 C21 1.419(3) . ?
O4 C11 1.376(3) . ?
O4 C10 1.420(3) . ?
C4 H4A 0.947(15) . ?
C4 H4B 0.947(15) . ?
C4 H4C 0.947(15) . ?
C5 H5A 0.939(15) . ?
C5 H5B 0.939(15) . ?
C5 H5C 0.939(15) . ?
O5 C9 1.379(3) . ?
O5 C10 1.412(3) . ?
C6 C7 1.382(3) . ?
C6 C12 1.413(3) . ?
C7 C8 1.393(3) . ?
C7 H7 0.93(3) . ?
C8 C9 1.373(3) . ?
C8 H8 0.93(3) . ?
C9 C11 1.379(3) . ?
C10 H10A 0.97(2) . ?
C10 H10B 0.97(2) . ?
C12 C11 1.379(3) . ?
C12 C13 1.526(3) . ?
C13 C14 1.522(3) . ?
C13 H13 0.97(3) . ?
C17 C16 1.380(4) . ?
C17 C18 1.386(3) . ?
C19 C18 1.386(3) . ?
C19 C14 1.393(3) . ?
C16 C15 1.398(3) . ?
C21 H21A 0.949(15) . ?
C21 H21B 0.949(15) . ?
C21 H21C 0.949(16) . ?
C20 H20A 0.989(15) . ?
C20 H20B 0.989(15) . ?
C20 H20C 0.989(15) . ?
C14 C15 1.390(3) . ?
C15 H15 0.92(3) . ?
C18 H18 0.87(3) . ?

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
C19 O1 C20 118.30(18) . . ?
C1 N1 N2 110.66(18) . . ?
C1 N1 C6 130.78(19) . . ?
N2 N1 C6 118.50(19) . . ?
N1 C1 C2 106.4(2) . . ?
N1 C1 H1 126.8 . . ?
C2 C1 H1 126.8 . . ?
C5 Si1 C4 109.88(13) . . ?
C5 Si1 C3 109.88(12) . . ?
C4 Si1 C3 111.46(12) . . ?
C5 Si1 C2 108.79(12) . . ?
C4 Si1 C2 109.45(11) . . ?
C3 Si1 C2 107.31(11) . . ?
N2 N3 C2 110.58(18) . . ?
C13 O3 H3 106(2) . . ?
Si1 C3 H3A 109.5 . . ?
Si1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
Si1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C2 N3 106.1(2) . . ?
C1 C2 Si1 130.52(18) . . ?
N3 C2 Si1 123.26(16) . . ?
C16 O2 C21 117.31(19) . . ?
N3 N2 N1 106.26(18) . . ?
C11 O4 C10 104.30(18) . . ?
Si1 C4 H4A 109.5 . . ?
Si1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
Si1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
Si1 C5 H5A 109.5 . . ?
Si1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
Si1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C9 O5 C10 104.64(19) . . ?
C7 C6 C12 122.4(2) . . ?
C7 C6 N1 116.74(19) . . ?
C12 C6 N1 120.8(2) . . ?
C6 C7 C8 122.0(2) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C9 C8 C7 115.7(2) . . ?
C9 C8 H8 122.2 . . ?
C7 C8 H8 122.2 . . ?
C8 C9 O5 128.3(2) . . ?
C8 C9 C11 122.1(2) . . ?
O5 C9 C11 109.49(19) . . ?
O5 C10 O4 108.9(2) . . ?
O5 C10 H10A 109.9 . . ?
O4 C10 H10A 109.9 . . ?
O5 C10 H10B 109.9 . . ?
O4 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C11 C12 C6 113.8(2) . . ?
C11 C12 C13 119.45(19) . . ?
C6 C12 C13 126.7(2) . . ?
O4 C11 C12 126.2(2) . . ?
O4 C11 C9 109.75(19) . . ?
C12 C11 C9 123.9(2) . . ?
O3 C13 C14 109.19(18) . . ?
O3 C13 C12 109.39(18) . . ?
C14 C13 C12 111.88(18) . . ?
O3 C13 H13 108.8 . . ?
C14 C13 H13 108.8 . . ?
C12 C13 H13 108.8 . . ?
C16 C17 C18 122.1(2) . . ?
C16 C17 Br1 119.71(18) . . ?
C18 C17 Br1 118.13(19) . . ?
O1 C19 C18 123.5(2) . . ?
O1 C19 C14 115.65(19) . . ?
C18 C19 C14 120.8(2) . . ?
O2 C16 C17 117.6(2) . . ?
O2 C16 C15 124.3(2) . . ?
C17 C16 C15 118.1(2) . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C14 C19 119.0(2) . . ?
C15 C14 C13 121.2(2) . . ?
C19 C14 C13 119.7(2) . . ?
C14 C15 C16 121.1(2) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C19 C18 C17 118.8(2) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?

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
N2 N1 C1 C2 0.6(3) . . . . ?
C6 N1 C1 C2 177.8(2) . . . . ?
N1 C1 C2 N3 -0.8(3) . . . . ?
N1 C1 C2 Si1 174.95(18) . . . . ?
N2 N3 C2 C1 0.7(3) . . . . ?
N2 N3 C2 Si1 -175.44(16) . . . . ?
C5 Si1 C2 C1 -76.1(3) . . . . ?
C4 Si1 C2 C1 44.0(3) . . . . ?
C3 Si1 C2 C1 165.1(2) . . . . ?
C5 Si1 C2 N3 99.0(2) . . . . ?
C4 Si1 C2 N3 -140.9(2) . . . . ?
C3 Si1 C2 N3 -19.8(2) . . . . ?
C2 N3 N2 N1 -0.3(2) . . . . ?
C1 N1 N2 N3 -0.2(2) . . . . ?
C6 N1 N2 N3 -177.82(19) . . . . ?
C1 N1 C6 C7 -131.2(3) . . . . ?
N2 N1 C6 C7 45.8(3) . . . . ?
C1 N1 C6 C12 49.8(3) . . . . ?
N2 N1 C6 C12 -133.2(2) . . . . ?
C12 C6 C7 C8 -0.2(4) . . . . ?
N1 C6 C7 C8 -179.2(2) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
C7 C8 C9 O5 177.3(2) . . . . ?
C7 C8 C9 C11 1.2(3) . . . . ?
C10 O5 C9 C8 173.9(3) . . . . ?
C10 O5 C9 C11 -9.6(3) . . . . ?
C9 O5 C10 O4 16.5(3) . . . . ?
C11 O4 C10 O5 -17.0(3) . . . . ?
C7 C6 C12 C11 0.5(3) . . . . ?
N1 C6 C12 C11 179.3(2) . . . . ?
C7 C6 C12 C13 -176.2(2) . . . . ?
N1 C6 C12 C13 2.7(3) . . . . ?
C10 O4 C11 C12 -172.3(2) . . . . ?
C10 O4 C11 C9 10.9(3) . . . . ?
C6 C12 C11 O4 -176.2(2) . . . . ?
C13 C12 C11 O4 0.7(3) . . . . ?
C6 C12 C11 C9 0.1(3) . . . . ?
C13 C12 C11 C9 177.1(2) . . . . ?
C8 C9 C11 O4 175.8(2) . . . . ?
O5 C9 C11 O4 -0.9(3) . . . . ?
C8 C9 C11 C12 -1.0(4) . . . . ?
O5 C9 C11 C12 -177.7(2) . . . . ?
C11 C12 C13 O3 -66.7(2) . . . . ?
C6 C12 C13 O3 109.8(2) . . . . ?
C11 C12 C13 C14 54.5(3) . . . . ?
C6 C12 C13 C14 -129.0(2) . . . . ?
C20 O1 C19 C18 -2.7(3) . . . . ?
C20 O1 C19 C14 178.1(2) . . . . ?
C21 O2 C16 C17 -164.7(2) . . . . ?
C21 O2 C16 C15 16.9(3) . . . . ?
C18 C17 C16 O2 -177.5(2) . . . . ?
Br1 C17 C16 O2 3.9(3) . . . . ?
C18 C17 C16 C15 1.1(4) . . . . ?
Br1 C17 C16 C15 -177.54(18) . . . . ?
O1 C19 C14 C15 -179.1(2) . . . . ?
C18 C19 C14 C15 1.6(3) . . . . ?
O1 C19 C14 C13 0.5(3) . . . . ?
C18 C19 C14 C13 -178.7(2) . . . . ?
O3 C13 C14 C15 -0.6(3) . . . . ?
C12 C13 C14 C15 -121.8(2) . . . . ?
O3 C13 C14 C19 179.80(19) . . . . ?
C12 C13 C14 C19 58.6(3) . . . . ?
C19 C14 C15 C16 -1.8(3) . . . . ?
C13 C14 C15 C16 178.5(2) . . . . ?
O2 C16 C15 C14 179.0(2) . . . . ?
C17 C16 C15 C14 0.5(4) . . . . ?
O1 C19 C18 C17 -179.3(2) . . . . ?
C14 C19 C18 C17 -0.1(4) . . . . ?
C16 C17 C18 C19 -1.3(4) . . . . ?
Br1 C17 C18 C19 177.35(18) . . . . ?

_refine_diff_density_max         0.757
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.093

_shelxl_version_number           2014-3



