# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_jmwcf106
_audit_block_doi                 10.5517/ccdc.csd.cc2844k4
_database_code_depnum_ccdc_archive 'CCDC 2089355'
loop_
_audit_author_name
_audit_author_address
'Jonathan White'
;University of Melbourne
Australia
;
_audit_update_record             
;
2021-06-11 deposited with the CCDC.	2023-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H18 B N O5 S'
_chemical_formula_weight         299.14
_chemical_oxdiff_usercomment     'CF BONONATE OF TOP  MOLECULE'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_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+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   33.1934(7)
_cell_length_b                   18.2476(4)
_cell_length_c                   9.1519(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5543.3(2)
_cell_formula_units_Z            16
_cell_measurement_temperature    100.00(1)
_cell_measurement_reflns_used    2834
_cell_measurement_theta_min      5.3420
_cell_measurement_theta_max      73.3520

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             2528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.575
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.055
_exptl_absorpt_coefficient_mu    2.250
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.51359
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.591
_oxdiff_exptl_absorpt_empirical_full_max 1.975
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5193
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         5.330
_diffrn_reflns_theta_max         78.016
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.697
_diffrn_reflns_point_group_measured_fraction_full 0.732
_reflns_number_total             2066
_reflns_number_gt                1969
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.357
_reflns_Friedel_fraction_max     0.391
_reflns_Friedel_fraction_full    0.435

_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 1.171.40.68a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0700P)²+11.6940P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 493 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2066
_refine_ls_number_parameters     214
_refine_ls_number_restraints     295
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1263
_refine_ls_wR_factor_gt          0.1246
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.077
_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
C12 C 0.37858(12) 0.5702(2) 0.6903(6) 0.0364(10) Uani 1 1 d . U . . .
H12A H 0.382698 0.544517 0.780557 0.055 Uiso 1 1 calc R U . . .
H12B H 0.377358 0.621964 0.708990 0.055 Uiso 1 1 calc R U . . .
H12C H 0.400505 0.560063 0.624961 0.055 Uiso 1 1 calc R U . . .
C1 C 0.33933(11) 0.4766(2) 0.5765(5) 0.0244(7) Uani 1 1 d . U . . .
C2 C 0.30448(10) 0.4584(2) 0.4972(4) 0.0220(7) Uani 1 1 d . U . . .
C3 C 0.30179(10) 0.3871(2) 0.4473(4) 0.0219(7) Uani 1 1 d . U . . .
H3 H 0.279038 0.372705 0.395398 0.026 Uiso 1 1 calc R U . . .
C4 C 0.33225(11) 0.3360(2) 0.4727(5) 0.0257(8) Uani 1 1 d . U . . .
C5 C 0.36633(12) 0.3543(2) 0.5521(5) 0.0312(9) Uani 1 1 d . U . . .
H5 H 0.386518 0.319949 0.568676 0.037 Uiso 1 1 calc R U . . .
C6 C 0.36963(11) 0.4252(2) 0.6062(5) 0.0294(9) Uani 1 1 d . U . . .
H6 H 0.391869 0.438461 0.662065 0.035 Uiso 1 1 calc R U . . .
C8 C 0.19857(11) 0.5161(2) 0.4326(5) 0.0283(8) Uani 1 1 d . U . . .
H8A H 0.175809 0.482901 0.427512 0.034 Uiso 1 1 calc R U . . .
H8B H 0.193447 0.557716 0.369248 0.034 Uiso 1 1 calc R U . . .
C9 C 0.20578(11) 0.5410(2) 0.5884(5) 0.0278(8) Uani 1 1 d . U . . .
H9A H 0.189068 0.583013 0.611807 0.033 Uiso 1 1 calc R U . . .
H9B H 0.199858 0.501878 0.656779 0.033 Uiso 1 1 calc R U . . .
C10 C 0.25861(13) 0.6400(2) 0.5669(6) 0.0337(9) Uani 1 1 d . U . . .
H10A H 0.282314 0.655203 0.620985 0.040 Uiso 1 1 calc R U . . .
H10B H 0.236094 0.670963 0.594570 0.040 Uiso 1 1 calc R U . . .
C11 C 0.26606(12) 0.6435(2) 0.4034(5) 0.0317(9) Uani 1 1 d . U . . .
H11A H 0.240822 0.647989 0.350789 0.038 Uiso 1 1 calc R U . . .
H11B H 0.283012 0.685070 0.379231 0.038 Uiso 1 1 calc R U . . .
B1 B 0.26985(12) 0.5178(2) 0.4554(5) 0.0231(8) Uani 1 1 d . U . . .
N1 N 0.24929(9) 0.56092(18) 0.5938(4) 0.0231(7) Uani 1 1 d . U . . .
O1 O 0.34150(8) 0.54663(14) 0.6251(3) 0.0281(6) Uani 1 1 d . U . . .
O4 O 0.23487(7) 0.47983(15) 0.3918(3) 0.0251(6) Uani 1 1 d . U . . .
O5 O 0.28549(8) 0.57728(15) 0.3676(3) 0.0289(6) Uani 1 1 d . U . . .
S1 S 0.32855(3) 0.24768(6) 0.39688(14) 0.0368(3) Uani 1 1 d D U . . .
O2 O 0.3162(3) 0.2539(4) 0.2455(6) 0.038(2) Uani 0.478(14) 1 d D U P A 1
O3 O 0.36870(19) 0.2171(7) 0.4101(12) 0.041(2) Uani 0.478(14) 1 d D U P A 1
C7 C 0.2980(3) 0.1933(6) 0.5055(15) 0.039(3) Uani 0.478(14) 1 d D U P A 1
H7A H 0.308423 0.192442 0.603323 0.059 Uiso 0.478(14) 1 calc R U P A 1
H7B H 0.271168 0.212980 0.506331 0.059 Uiso 0.478(14) 1 calc R U P A 1
H7C H 0.297449 0.144372 0.467047 0.059 Uiso 0.478(14) 1 calc R U P A 1
O2A O 0.2910(2) 0.2475(4) 0.3123(10) 0.053(3) Uani 0.522(14) 1 d D U P A 2
O3A O 0.3670(3) 0.2200(9) 0.350(2) 0.075(4) Uani 0.522(14) 1 d D U P A 2
C7A C 0.3115(5) 0.1952(7) 0.5436(13) 0.055(3) Uani 0.522(14) 1 d D U P A 2
H7A1 H 0.285836 0.213394 0.575656 0.082 Uiso 0.522(14) 1 calc R U P A 2
H7A2 H 0.308757 0.145050 0.513511 0.082 Uiso 0.522(14) 1 calc R U P A 2
H7A3 H 0.330502 0.198265 0.622431 0.082 Uiso 0.522(14) 1 calc R U P A 2
H1 H 0.2594(13) 0.551(3) 0.684(6) 0.023(11) Uiso 1 1 d . . . . .


_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
C12 O1 1.434(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C1 O1 1.355(4) . ?
C1 C6 1.402(5) . ?
C1 C2 1.405(5) . ?
C2 C3 1.382(5) . ?
C2 B1 1.626(5) . ?
C3 C4 1.394(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(6) . ?
C4 S1 1.760(4) . ?
C5 C6 1.389(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 O4 1.425(4) . ?
C8 C9 1.515(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N1 1.490(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N1 1.497(5) . ?
C10 C11 1.518(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O5 1.408(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
B1 O5 1.447(5) . ?
B1 O4 1.472(5) . ?
B1 N1 1.640(6) . ?
N1 H1 0.91(6) . ?
S1 O3A 1.439(5) . ?
S1 O2 1.449(5) . ?
S1 O3 1.450(5) . ?
S1 O2A 1.467(5) . ?
S1 C7 1.732(8) . ?
S1 C7A 1.744(8) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C7A H7A1 0.9600 . ?
C7A H7A2 0.9600 . ?
C7A H7A3 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C1 C6 122.0(3) . . ?
O1 C1 C2 115.8(3) . . ?
C6 C1 C2 122.2(3) . . ?
C3 C2 C1 116.5(3) . . ?
C3 C2 B1 120.3(3) . . ?
C1 C2 B1 123.1(3) . . ?
C2 C3 C4 121.8(3) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 121.3(4) . . ?
C5 C4 S1 119.0(3) . . ?
C3 C4 S1 119.7(3) . . ?
C4 C5 C6 118.4(4) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
O4 C8 C9 104.6(3) . . ?
O4 C8 H8A 110.8 . . ?
C9 C8 H8A 110.8 . . ?
O4 C8 H8B 110.8 . . ?
C9 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
N1 C9 C8 104.9(3) . . ?
N1 C9 H9A 110.8 . . ?
C8 C9 H9A 110.8 . . ?
N1 C9 H9B 110.8 . . ?
C8 C9 H9B 110.8 . . ?
H9A C9 H9B 108.8 . . ?
N1 C10 C11 103.6(3) . . ?
N1 C10 H10A 111.0 . . ?
C11 C10 H10A 111.0 . . ?
N1 C10 H10B 111.0 . . ?
C11 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
O5 C11 C10 105.6(3) . . ?
O5 C11 H11A 110.6 . . ?
C10 C11 H11A 110.6 . . ?
O5 C11 H11B 110.6 . . ?
C10 C11 H11B 110.6 . . ?
H11A C11 H11B 108.8 . . ?
O5 B1 O4 114.6(4) . . ?
O5 B1 C2 112.2(3) . . ?
O4 B1 C2 109.7(3) . . ?
O5 B1 N1 102.6(3) . . ?
O4 B1 N1 101.7(3) . . ?
C2 B1 N1 115.6(3) . . ?
C9 N1 C10 115.5(3) . . ?
C9 N1 B1 105.1(3) . . ?
C10 N1 B1 104.5(3) . . ?
C9 N1 H1 110(3) . . ?
C10 N1 H1 105(3) . . ?
B1 N1 H1 117(3) . . ?
C1 O1 C12 117.7(3) . . ?
C8 O4 B1 110.2(3) . . ?
C11 O5 B1 110.5(3) . . ?
O2 S1 O3 111.7(5) . . ?
O3A S1 O2A 126.4(7) . . ?
O2 S1 C7 115.3(5) . . ?
O3 S1 C7 105.7(6) . . ?
O3A S1 C7A 109.1(9) . . ?
O2A S1 C7A 97.4(6) . . ?
O3A S1 C4 112.2(7) . . ?
O2 S1 C4 109.0(3) . . ?
O3 S1 C4 104.8(5) . . ?
O2A S1 C4 105.6(3) . . ?
C7 S1 C4 109.8(5) . . ?
C7A S1 C4 102.8(5) . . ?
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 . . ?
S1 C7A H7A1 109.5 . . ?
S1 C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
S1 C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 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
O1 C1 C2 C3 -179.8(3) . . . . ?
C6 C1 C2 C3 -1.1(6) . . . . ?
O1 C1 C2 B1 3.9(5) . . . . ?
C6 C1 C2 B1 -177.3(4) . . . . ?
C1 C2 C3 C4 -0.8(6) . . . . ?
B1 C2 C3 C4 175.6(4) . . . . ?
C2 C3 C4 C5 1.4(6) . . . . ?
C2 C3 C4 S1 -176.1(3) . . . . ?
C3 C4 C5 C6 -0.1(7) . . . . ?
S1 C4 C5 C6 177.4(3) . . . . ?
C4 C5 C6 C1 -1.7(7) . . . . ?
O1 C1 C6 C5 -179.0(4) . . . . ?
C2 C1 C6 C5 2.3(6) . . . . ?
O4 C8 C9 N1 35.4(4) . . . . ?
N1 C10 C11 O5 -35.9(4) . . . . ?
C3 C2 B1 O5 -116.5(4) . . . . ?
C1 C2 B1 O5 59.7(5) . . . . ?
C3 C2 B1 O4 12.1(5) . . . . ?
C1 C2 B1 O4 -171.7(4) . . . . ?
C3 C2 B1 N1 126.4(4) . . . . ?
C1 C2 B1 N1 -57.5(5) . . . . ?
C8 C9 N1 C10 93.7(4) . . . . ?
C8 C9 N1 B1 -20.8(4) . . . . ?
C11 C10 N1 C9 -92.2(4) . . . . ?
C11 C10 N1 B1 22.7(4) . . . . ?
O5 B1 N1 C9 118.9(3) . . . . ?
O4 B1 N1 C9 0.0(4) . . . . ?
C2 B1 N1 C9 -118.7(4) . . . . ?
O5 B1 N1 C10 -3.1(4) . . . . ?
O4 B1 N1 C10 -121.9(3) . . . . ?
C2 B1 N1 C10 119.3(4) . . . . ?
C6 C1 O1 C12 9.0(6) . . . . ?
C2 C1 O1 C12 -172.3(4) . . . . ?
C9 C8 O4 B1 -37.1(4) . . . . ?
O5 B1 O4 C8 -87.1(4) . . . . ?
C2 B1 O4 C8 145.7(3) . . . . ?
N1 B1 O4 C8 22.8(4) . . . . ?
C10 C11 O5 B1 35.9(4) . . . . ?
O4 B1 O5 C11 89.2(4) . . . . ?
C2 B1 O5 C11 -144.8(3) . . . . ?
N1 B1 O5 C11 -20.1(4) . . . . ?
C5 C4 S1 O3A -34.8(9) . . . . ?
C3 C4 S1 O3A 142.7(9) . . . . ?
C5 C4 S1 O2 -132.2(5) . . . . ?
C3 C4 S1 O2 45.3(5) . . . . ?
C5 C4 S1 O3 -12.5(6) . . . . ?
C3 C4 S1 O3 165.0(6) . . . . ?
C5 C4 S1 O2A -176.0(6) . . . . ?
C3 C4 S1 O2A 1.4(6) . . . . ?
C5 C4 S1 C7 100.6(6) . . . . ?
C3 C4 S1 C7 -82.0(6) . . . . ?
C5 C4 S1 C7A 82.3(7) . . . . ?
C3 C4 S1 C7A -100.2(7) . . . . ?

_refine_diff_density_max         0.343
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_bipet1
_audit_block_doi                 10.5517/ccdc.csd.cc2cycd3
_database_code_depnum_ccdc_archive 'CCDC 2202965'
loop_
_audit_author_name
_audit_author_address
'Jonathan White'
;University of Melbourne
Australia
;
_audit_update_record             
;
2022-08-23 deposited with the CCDC.	2023-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H25 F N4 O6 S'
_chemical_formula_weight         492.52
_chemical_oxdiff_usercomment     "From Catherine's Click sample 1"

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   4.9614(5)
_cell_length_b                   19.3463(15)
_cell_length_c                   24.007(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.220(10)
_cell_angle_gamma                90
_cell_volume                     2303.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    800
_cell_measurement_theta_min      2.9260
_cell_measurement_theta_max      53.6370

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    1.732
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.31987
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.305
_oxdiff_exptl_absorpt_empirical_full_max 2.264
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9311
_diffrn_reflns_av_unetI/netI     0.1389
_diffrn_reflns_av_R_equivalents  0.1148
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.934
_diffrn_reflns_theta_max         68.964
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measured_fraction_theta_full 0.942
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_Laue_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_point_group_measured_fraction_full 0.942
_reflns_number_total             3911
_reflns_number_gt                2459
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0759P)²+4.1114P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3911
_refine_ls_number_parameters     322
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1739
_refine_ls_R_factor_gt           0.1084
_refine_ls_wR_factor_ref         0.2404
_refine_ls_wR_factor_gt          0.2133
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.146
_refine_ls_shift/su_max          0.002
_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
C22 C -0.0190(15) 0.1351(4) 0.7390(3) 0.0418(19) Uani 1 1 d . . . . .
H22A H -0.128593 0.103211 0.716310 0.063 Uiso 1 1 calc R U . . .
H22B H -0.135522 0.170329 0.755217 0.063 Uiso 1 1 calc R U . . .
H22C H 0.073475 0.109344 0.768931 0.063 Uiso 1 1 calc R U . . .
C1 C 0.2258(14) 0.2395(3) 0.7088(3) 0.0307(16) Uani 1 1 d . . . . .
H1 H 0.125731 0.264226 0.735614 0.037 Uiso 1 1 calc R U . . .
C21 C 0.8454(18) 0.3649(4) 0.8136(4) 0.062(3) Uani 1 1 d . . . . .
H21A H 0.980544 0.398456 0.801678 0.093 Uiso 1 1 calc R U . . .
H21B H 0.934718 0.327524 0.834441 0.093 Uiso 1 1 calc R U . . .
H21C H 0.715428 0.387988 0.837551 0.093 Uiso 1 1 calc R U . . .
C2 C 0.4020(13) 0.2749(3) 0.6779(3) 0.0261(15) Uani 1 1 d . . . . .
C3 C 0.5466(12) 0.2369(3) 0.6357(3) 0.0244(15) Uani 1 1 d . . . . .
C4 C 0.5035(13) 0.1650(3) 0.6311(3) 0.0243(14) Uani 1 1 d . . . . .
C5 C 0.3146(13) 0.1287(3) 0.6654(3) 0.0258(15) Uani 1 1 d . . . . .
C6 C 0.6508(12) 0.1269(3) 0.5915(3) 0.0273(15) Uani 1 1 d . . . . .
H6 H 0.621783 0.078577 0.587834 0.033 Uiso 1 1 calc R U . . .
C7 C 0.8339(13) 0.1589(3) 0.5587(3) 0.0281(15) Uani 1 1 d . . . . .
H7 H 0.937001 0.132296 0.533578 0.034 Uiso 1 1 calc R U . . .
C8 C 0.8715(13) 0.2308(3) 0.5616(3) 0.0269(15) Uani 1 1 d . . . . .
C9 C 0.7291(13) 0.2691(3) 0.6003(3) 0.0259(15) Uani 1 1 d . . . . .
H9 H 0.756030 0.317675 0.602698 0.031 Uiso 1 1 calc R U . . .
C10 C 0.4242(12) 0.3521(3) 0.6857(3) 0.0258(15) Uani 1 1 d . . . . .
C11 C 0.5712(14) 0.3806(3) 0.7298(3) 0.0317(16) Uani 1 1 d . . . . .
C12 C 0.5736(14) 0.4525(3) 0.7383(3) 0.0334(17) Uani 1 1 d . . . . .
H12 H 0.669848 0.471983 0.769174 0.040 Uiso 1 1 calc R U . . .
C13 C 0.4347(14) 0.4940(3) 0.7015(3) 0.0330(17) Uani 1 1 d . . . . .
H13 H 0.441633 0.542723 0.706244 0.040 Uiso 1 1 calc R U . . .
C14 C 0.2837(14) 0.4666(3) 0.6573(3) 0.0328(17) Uani 1 1 d . . . . .
C15 C 0.2818(13) 0.3945(3) 0.6496(3) 0.0292(16) Uani 1 1 d . . . . .
H15 H 0.181811 0.374937 0.619303 0.035 Uiso 1 1 calc R U . . .
C16 C 0.2759(14) 0.5192(4) 0.5489(3) 0.0352(17) Uani 1 1 d . . . . .
H16A H 0.289718 0.471882 0.534603 0.053 Uiso 1 1 calc R U . . .
H16B H 0.457134 0.537838 0.555883 0.053 Uiso 1 1 calc R U . . .
H16C H 0.180750 0.548094 0.521285 0.053 Uiso 1 1 calc R U . . .
C17 C 1.0629(13) 0.2631(3) 0.5247(3) 0.0257(15) Uani 1 1 d . . . . .
C18 C 1.2319(13) 0.2335(3) 0.4861(3) 0.0312(16) Uani 1 1 d . . . . .
H18 H 1.250124 0.185794 0.477439 0.037 Uiso 1 1 calc R U . . .
C19 C 1.5629(15) 0.2848(3) 0.4192(3) 0.0391(18) Uani 1 1 d . . . . .
H19A H 1.635998 0.237423 0.415857 0.047 Uiso 1 1 calc R U . . .
H19B H 1.714298 0.316334 0.428638 0.047 Uiso 1 1 calc R U . . .
C20 C 1.4348(16) 0.3061(4) 0.3654(3) 0.046(2) Uani 1 1 d . . . . .
H20A H 1.355631 0.352818 0.369057 0.056 Uiso 1 1 calc R U . . .
H20B H 1.572337 0.307881 0.336126 0.056 Uiso 1 1 calc R U . . .
F1 F 1.2346(12) 0.2591(3) 0.3503(2) 0.0767(17) Uani 1 1 d . . . . .
N1 N 0.1817(10) 0.1686(3) 0.7038(2) 0.0272(13) Uani 1 1 d . . . . .
N2 N 1.1020(12) 0.3340(3) 0.5225(2) 0.0354(14) Uani 1 1 d . . . . .
N3 N 1.2855(12) 0.3480(3) 0.4851(2) 0.0385(15) Uani 1 1 d . . . . .
N4 N 1.3640(11) 0.2868(3) 0.4638(2) 0.0315(13) Uani 1 1 d . . . . .
O1 O 0.2661(9) 0.0657(2) 0.66241(19) 0.0324(12) Uani 1 1 d . . . . .
O2 O 0.7028(10) 0.3360(2) 0.7641(2) 0.0391(12) Uani 1 1 d . . . . .
O3 O 0.1021(12) 0.5884(2) 0.6335(2) 0.0520(15) Uani 1 1 d . . . . .
O4 O -0.1574(10) 0.4868(3) 0.6001(2) 0.0547(16) Uani 1 1 d . . . . .
O5 O 0.2241(11) -0.0119(3) 0.5679(3) 0.0499(15) Uani 1 1 d D . . . .
O6 O -0.2758(11) -0.0627(3) 0.5333(3) 0.0503(15) Uani 1 1 d D . . . .
S1 S 0.0978(4) 0.51876(8) 0.61094(8) 0.0366(5) Uani 1 1 d . . . . .
H5A H 0.270(16) 0.011(4) 0.595(2) 0.055 Uiso 1 1 d D U . . .
H6A H -0.425(8) -0.058(4) 0.547(3) 0.055 Uiso 1 1 d D U . . .
H5B H 0.075(7) -0.027(4) 0.559(3) 0.055 Uiso 1 1 d D U . . .
H6B H -0.257(17) -0.037(4) 0.506(2) 0.055 Uiso 1 1 d D 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
C22 N1 1.470(8) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C1 C2 1.346(9) . ?
C1 N1 1.392(8) . ?
C1 H1 0.9500 . ?
C21 O2 1.480(9) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C2 C3 1.454(8) . ?
C2 C10 1.509(8) . ?
C3 C9 1.401(8) . ?
C3 C4 1.413(8) . ?
C4 C6 1.417(8) . ?
C4 C5 1.442(8) . ?
C5 O1 1.244(7) . ?
C5 N1 1.382(8) . ?
C6 C7 1.364(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.406(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.393(8) . ?
C8 C17 1.454(8) . ?
C9 H9 0.9500 . ?
C10 C15 1.378(9) . ?
C10 C11 1.386(9) . ?
C11 O2 1.352(8) . ?
C11 C12 1.407(9) . ?
C12 C13 1.370(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(10) . ?
C13 H13 0.9500 . ?
C14 C15 1.408(8) . ?
C14 S1 1.750(7) . ?
C15 H15 0.9500 . ?
C16 S1 1.749(7) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 N2 1.386(7) . ?
C17 C18 1.386(9) . ?
C18 N4 1.339(8) . ?
C18 H18 0.9500 . ?
C19 N4 1.472(9) . ?
C19 C20 1.487(11) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 F1 1.389(9) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
N2 N3 1.321(7) . ?
N3 N4 1.351(7) . ?
O3 S1 1.452(5) . ?
O4 S1 1.428(5) . ?
O5 H5A 0.820(10) . ?
O5 H5B 0.820(10) . ?
O6 H6A 0.822(10) . ?
O6 H6B 0.822(10) . ?

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
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C2 C1 N1 123.8(5) . . ?
C2 C1 H1 118.1 . . ?
N1 C1 H1 118.1 . . ?
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 . . ?
C1 C2 C3 117.6(5) . . ?
C1 C2 C10 118.8(5) . . ?
C3 C2 C10 123.4(5) . . ?
C9 C3 C4 119.3(5) . . ?
C9 C3 C2 122.3(5) . . ?
C4 C3 C2 118.4(5) . . ?
C3 C4 C6 119.0(5) . . ?
C3 C4 C5 122.2(5) . . ?
C6 C4 C5 118.8(5) . . ?
O1 C5 N1 119.4(5) . . ?
O1 C5 C4 124.8(6) . . ?
N1 C5 C4 115.8(5) . . ?
C7 C6 C4 120.7(5) . . ?
C7 C6 H6 119.6 . . ?
C4 C6 H6 119.6 . . ?
C6 C7 C8 120.6(6) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 119.4(6) . . ?
C9 C8 C17 121.7(5) . . ?
C7 C8 C17 118.9(5) . . ?
C8 C9 C3 120.8(5) . . ?
C8 C9 H9 119.6 . . ?
C3 C9 H9 119.6 . . ?
C15 C10 C11 119.8(6) . . ?
C15 C10 C2 118.4(6) . . ?
C11 C10 C2 121.6(6) . . ?
O2 C11 C10 116.8(5) . . ?
O2 C11 C12 122.6(6) . . ?
C10 C11 C12 120.5(6) . . ?
C13 C12 C11 118.8(6) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C14 121.7(6) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C13 C14 C15 118.7(6) . . ?
C13 C14 S1 122.3(5) . . ?
C15 C14 S1 119.0(6) . . ?
C10 C15 C14 120.4(6) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
S1 C16 H16A 109.5 . . ?
S1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
S1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 C18 107.3(5) . . ?
N2 C17 C8 122.8(5) . . ?
C18 C17 C8 129.9(5) . . ?
N4 C18 C17 104.8(6) . . ?
N4 C18 H18 127.6 . . ?
C17 C18 H18 127.6 . . ?
N4 C19 C20 110.2(6) . . ?
N4 C19 H19A 109.6 . . ?
C20 C19 H19A 109.6 . . ?
N4 C19 H19B 109.6 . . ?
C20 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
F1 C20 C19 109.6(6) . . ?
F1 C20 H20A 109.7 . . ?
C19 C20 H20A 109.7 . . ?
F1 C20 H20B 109.7 . . ?
C19 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
C5 N1 C1 122.1(5) . . ?
C5 N1 C22 118.4(5) . . ?
C1 N1 C22 119.5(5) . . ?
N3 N2 C17 109.1(5) . . ?
N2 N3 N4 106.6(5) . . ?
C18 N4 N3 112.2(5) . . ?
C18 N4 C19 127.8(5) . . ?
N3 N4 C19 120.0(5) . . ?
C11 O2 C21 117.7(5) . . ?
H5A O5 H5B 130(9) . . ?
H6A O6 H6B 112(9) . . ?
O4 S1 O3 118.4(3) . . ?
O4 S1 C16 108.0(4) . . ?
O3 S1 C16 108.0(3) . . ?
O4 S1 C14 108.6(3) . . ?
O3 S1 C14 107.1(3) . . ?
C16 S1 C14 106.0(3) . . ?

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
N1 C1 C2 C3 2.3(10) . . . . ?
N1 C1 C2 C10 177.7(6) . . . . ?
C1 C2 C3 C9 178.3(7) . . . . ?
C10 C2 C3 C9 3.0(10) . . . . ?
C1 C2 C3 C4 -2.8(9) . . . . ?
C10 C2 C3 C4 -178.0(6) . . . . ?
C9 C3 C4 C6 1.4(10) . . . . ?
C2 C3 C4 C6 -177.6(6) . . . . ?
C9 C3 C4 C5 -178.7(6) . . . . ?
C2 C3 C4 C5 2.3(10) . . . . ?
C3 C4 C5 O1 178.9(6) . . . . ?
C6 C4 C5 O1 -1.2(10) . . . . ?
C3 C4 C5 N1 -1.2(9) . . . . ?
C6 C4 C5 N1 178.7(6) . . . . ?
C3 C4 C6 C7 0.7(10) . . . . ?
C5 C4 C6 C7 -179.2(6) . . . . ?
C4 C6 C7 C8 -2.9(10) . . . . ?
C6 C7 C8 C9 3.0(10) . . . . ?
C6 C7 C8 C17 -178.2(6) . . . . ?
C7 C8 C9 C3 -0.9(10) . . . . ?
C17 C8 C9 C3 -179.7(6) . . . . ?
C4 C3 C9 C8 -1.3(10) . . . . ?
C2 C3 C9 C8 177.7(6) . . . . ?
C1 C2 C10 C15 -96.7(8) . . . . ?
C3 C2 C10 C15 78.5(8) . . . . ?
C1 C2 C10 C11 79.7(8) . . . . ?
C3 C2 C10 C11 -105.1(8) . . . . ?
C15 C10 C11 O2 179.0(6) . . . . ?
C2 C10 C11 O2 2.6(9) . . . . ?
C15 C10 C11 C12 0.8(9) . . . . ?
C2 C10 C11 C12 -175.6(6) . . . . ?
O2 C11 C12 C13 -180.0(6) . . . . ?
C10 C11 C12 C13 -1.9(10) . . . . ?
C11 C12 C13 C14 2.5(10) . . . . ?
C12 C13 C14 C15 -2.0(10) . . . . ?
C12 C13 C14 S1 178.3(5) . . . . ?
C11 C10 C15 C14 -0.3(9) . . . . ?
C2 C10 C15 C14 176.2(5) . . . . ?
C13 C14 C15 C10 0.9(9) . . . . ?
S1 C14 C15 C10 -179.4(5) . . . . ?
C9 C8 C17 N2 -4.9(10) . . . . ?
C7 C8 C17 N2 176.4(6) . . . . ?
C9 C8 C17 C18 176.1(7) . . . . ?
C7 C8 C17 C18 -2.7(11) . . . . ?
N2 C17 C18 N4 0.9(8) . . . . ?
C8 C17 C18 N4 -180.0(7) . . . . ?
N4 C19 C20 F1 -63.4(7) . . . . ?
O1 C5 N1 C1 -179.5(6) . . . . ?
C4 C5 N1 C1 0.5(9) . . . . ?
O1 C5 N1 C22 -1.7(9) . . . . ?
C4 C5 N1 C22 178.4(6) . . . . ?
C2 C1 N1 C5 -1.2(10) . . . . ?
C2 C1 N1 C22 -179.0(7) . . . . ?
C18 C17 N2 N3 -0.3(8) . . . . ?
C8 C17 N2 N3 -179.5(6) . . . . ?
C17 N2 N3 N4 -0.4(7) . . . . ?
C17 C18 N4 N3 -1.1(8) . . . . ?
C17 C18 N4 C19 -177.9(6) . . . . ?
N2 N3 N4 C18 1.0(8) . . . . ?
N2 N3 N4 C19 178.0(6) . . . . ?
C20 C19 N4 C18 101.4(8) . . . . ?
C20 C19 N4 N3 -75.1(8) . . . . ?
C10 C11 O2 C21 -175.8(7) . . . . ?
C12 C11 O2 C21 2.3(10) . . . . ?
C13 C14 S1 O4 -137.9(6) . . . . ?
C15 C14 S1 O4 42.4(6) . . . . ?
C13 C14 S1 O3 -8.9(7) . . . . ?
C15 C14 S1 O3 171.4(5) . . . . ?
C13 C14 S1 C16 106.2(6) . . . . ?
C15 C14 S1 C16 -73.5(6) . . . . ?

_refine_diff_density_max         0.377
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.078

####################################################################### 
# 
# 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_CMPD4
_audit_block_doi                 10.5517/ccdc.csd.cc2cyfb3
_database_code_depnum_ccdc_archive 'CCDC 2203025'
loop_
_audit_author_name
_audit_author_address
'Jonathan White'
;University of Melbourne
Australia
;
_audit_update_record             
;
2022-08-23 deposited with the CCDC.	2023-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 Br N O Si'
_chemical_formula_weight         334.29
_chemical_oxdiff_usercomment     "cathereine's sonagashira bromide"

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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                   6.1065(2)
_cell_length_b                   27.0005(6)
_cell_length_c                   18.7830(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.064(2)
_cell_angle_gamma                90
_cell_volume                     3084.83(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    8533
_cell_measurement_theta_min      4.9890
_cell_measurement_theta_max      77.3290

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.028
_exptl_crystal_size_min          0.022
_exptl_absorpt_coefficient_mu    4.306
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.38767
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.137
_oxdiff_exptl_absorpt_empirical_full_max 2.781
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31002
_diffrn_reflns_av_unetI/netI     0.0901
_diffrn_reflns_av_R_equivalents  0.1382
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.873
_diffrn_reflns_theta_max         78.279
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             6438
_reflns_number_gt                5201
_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 1.171.40.68a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1566P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6438
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0733
_refine_ls_wR_factor_ref         0.2100
_refine_ls_wR_factor_gt          0.1934
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.002
_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
C1 C 1.0490(8) 0.68952(15) 0.2208(2) 0.0260(8) Uani 1 1 d . . . . .
C1A C 0.0189(7) 0.81045(15) 0.3784(2) 0.0250(8) Uani 1 1 d . . . . .
C2 C 0.9081(7) 0.72669(15) 0.2061(2) 0.0265(8) Uani 1 1 d . . . . .
H2 H 0.921675 0.746110 0.165872 0.032 Uiso 1 1 calc R U . . .
C2A C 0.1410(7) 0.77085(16) 0.4013(2) 0.0278(8) Uani 1 1 d . . . . .
H2A H 0.259480 0.761032 0.376784 0.033 Uiso 1 1 calc R U . . .
C3 C 0.7071(7) 0.70895(14) 0.3085(2) 0.0240(8) Uani 1 1 d . . . . .
C3A C -0.0877(7) 0.75496(15) 0.4981(2) 0.0250(8) Uani 1 1 d . . . . .
C4 C 0.8586(7) 0.66657(15) 0.3237(2) 0.0249(8) Uani 1 1 d . . . . .
C4A C -0.2160(7) 0.79902(15) 0.4748(2) 0.0259(8) Uani 1 1 d . . . . .
C5 C 0.8215(8) 0.63549(16) 0.3810(2) 0.0288(9) Uani 1 1 d . . . . .
H5 H 0.705347 0.641816 0.408499 0.035 Uiso 1 1 calc R U . . .
C5A C -0.3927(8) 0.81312(17) 0.5127(2) 0.0290(9) Uani 1 1 d . . . . .
H5A H -0.429173 0.794159 0.551260 0.035 Uiso 1 1 calc R U . . .
C6 C 0.9576(8) 0.59547(15) 0.3965(2) 0.0292(9) Uani 1 1 d . . . . .
H6 H 0.931391 0.574421 0.434007 0.035 Uiso 1 1 calc R U . . .
C6A C -0.5141(8) 0.85517(17) 0.4933(3) 0.0319(9) Uani 1 1 d . . . . .
H6A H -0.630658 0.864419 0.519071 0.038 Uiso 1 1 calc R U . . .
C7 C 1.1371(7) 0.58632(15) 0.3555(2) 0.0236(8) Uani 1 1 d . . . . .
C7A C -0.4612(7) 0.88386(15) 0.4347(2) 0.0257(8) Uani 1 1 d . . . . .
C8 C 1.1768(7) 0.61749(14) 0.2988(2) 0.0244(8) Uani 1 1 d . . . . .
H8 H 1.297191 0.612012 0.272783 0.029 Uiso 1 1 calc R U . . .
C8A C -0.2873(7) 0.86948(15) 0.3957(2) 0.0243(8) Uani 1 1 d . . . . .
H8A H -0.253772 0.888144 0.356488 0.029 Uiso 1 1 calc R U . . .
C9 C 1.0326(7) 0.65744(13) 0.2813(2) 0.0223(8) Uani 1 1 d . . . . .
C9A C -0.1634(7) 0.82738(14) 0.4150(2) 0.0224(8) Uani 1 1 d . . . . .
C10 C 1.2748(7) 0.54319(15) 0.3701(2) 0.0261(8) Uani 1 1 d . . . . .
C10A C -0.5816(8) 0.92843(16) 0.4156(2) 0.0278(8) Uani 1 1 d . . . . .
C11 C 1.3806(7) 0.50651(15) 0.3800(2) 0.0262(8) Uani 1 1 d . . . . .
C11A C -0.6834(8) 0.96558(16) 0.3997(2) 0.0291(9) Uani 1 1 d . . . . .
C12 C 1.4923(10) 0.41563(17) 0.2988(3) 0.0384(11) Uani 1 1 d . . . . .
H12A H 1.568281 0.384475 0.301219 0.058 Uiso 1 1 calc R U . . .
H12B H 1.338478 0.410084 0.286107 0.058 Uiso 1 1 calc R U . . .
H12C H 1.550647 0.436255 0.263391 0.058 Uiso 1 1 calc R U . . .
C12A C -0.9513(11) 1.0547(2) 0.4387(3) 0.0461(13) Uani 1 1 d . . . . .
H12D H -1.033332 1.082783 0.419612 0.069 Uiso 1 1 calc R U . . .
H12E H -1.045774 1.033658 0.463561 0.069 Uiso 1 1 calc R U . . .
H12F H -0.831544 1.065917 0.471315 0.069 Uiso 1 1 calc R U . . .
C13 C 1.8244(9) 0.4595(2) 0.4136(4) 0.0465(13) Uani 1 1 d . . . . .
H13A H 1.903958 0.428840 0.417597 0.070 Uiso 1 1 calc R U . . .
H13B H 1.882911 0.479925 0.377917 0.070 Uiso 1 1 calc R U . . .
H13C H 1.838760 0.476387 0.458721 0.070 Uiso 1 1 calc R U . . .
C13A C -1.0734(9) 0.9955(2) 0.3037(3) 0.0401(11) Uani 1 1 d . . . . .
H13D H -1.160836 1.022650 0.284206 0.060 Uiso 1 1 calc R U . . .
H13E H -1.015947 0.977346 0.265492 0.060 Uiso 1 1 calc R U . . .
H13F H -1.162860 0.973993 0.329681 0.060 Uiso 1 1 calc R U . . .
C14 C 1.4171(8) 0.40807(18) 0.4573(3) 0.0342(10) Uani 1 1 d . . . . .
H14A H 1.494381 0.377090 0.461166 0.051 Uiso 1 1 calc R U . . .
H14B H 1.435010 0.425078 0.502331 0.051 Uiso 1 1 calc R U . . .
H14C H 1.263701 0.402038 0.444581 0.051 Uiso 1 1 calc R U . . .
C14A C -0.6538(10) 1.0588(2) 0.3156(4) 0.0496(14) Uani 1 1 d . . . . .
H14D H -0.731565 1.087469 0.296717 0.074 Uiso 1 1 calc R U . . .
H14E H -0.530946 1.069029 0.347667 0.074 Uiso 1 1 calc R U . . .
H14F H -0.601932 1.039982 0.277117 0.074 Uiso 1 1 calc R U . . .
C15 C 0.5965(8) 0.77879(15) 0.2321(3) 0.0304(9) Uani 1 1 d . . . . .
H15A H 0.608049 0.801823 0.271219 0.046 Uiso 1 1 calc R U . . .
H15B H 0.447938 0.767041 0.224463 0.046 Uiso 1 1 calc R U . . .
H15C H 0.636745 0.794970 0.189686 0.046 Uiso 1 1 calc R U . . .
C15A C 0.2357(9) 0.70323(16) 0.4859(3) 0.0340(10) Uani 1 1 d . . . . .
H15D H 0.342575 0.697644 0.452228 0.051 Uiso 1 1 calc R U . . .
H15E H 0.149125 0.673861 0.489948 0.051 Uiso 1 1 calc R U . . .
H15F H 0.309574 0.711223 0.531722 0.051 Uiso 1 1 calc R U . . .
N1 N 0.7446(6) 0.73678(12) 0.2490(2) 0.0267(7) Uani 1 1 d . . . . .
N1A N 0.0901(6) 0.74500(13) 0.4609(2) 0.0262(7) Uani 1 1 d . . . . .
O1 O 0.5563(6) 0.71893(12) 0.34517(19) 0.0319(7) Uani 1 1 d . . . . .
O1A O -0.1308(6) 0.72856(11) 0.54894(17) 0.0304(7) Uani 1 1 d . . . . .
Si1 Si 1.52975(18) 0.44679(4) 0.38735(6) 0.0241(3) Uani 1 1 d . . . . .
Si2 Si -0.8419(2) 1.01973(4) 0.36489(7) 0.0280(3) Uani 1 1 d . . . . .
Br1 Br 1.26680(8) 0.67690(2) 0.15675(3) 0.03206(19) Uani 1 1 d . . . . .
Br1A Br 0.09942(8) 0.84426(2) 0.29602(2) 0.02940(18) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.334(6) . ?
C1 C9 1.440(6) . ?
C1 Br1 1.901(5) . ?
C1A C2A 1.352(6) . ?
C1A C9A 1.434(6) . ?
C1A Br1A 1.899(4) . ?
C2 N1 1.365(6) . ?
C2 H2 0.9300 . ?
C2A N1A 1.378(6) . ?
C2A H2A 0.9300 . ?
C3 O1 1.228(5) . ?
C3 N1 1.382(6) . ?
C3 C4 1.483(6) . ?
C3A O1A 1.238(6) . ?
C3A N1A 1.369(6) . ?
C3A C4A 1.470(6) . ?
C4 C5 1.399(6) . ?
C4 C9 1.404(6) . ?
C4A C5A 1.398(7) . ?
C4A C9A 1.419(6) . ?
C5 C6 1.379(6) . ?
C5 H5 0.9300 . ?
C5A C6A 1.387(6) . ?
C5A H5A 0.9300 . ?
C6 C7 1.416(6) . ?
C6 H6 0.9300 . ?
C6A C7A 1.407(7) . ?
C6A H6A 0.9300 . ?
C7 C8 1.395(6) . ?
C7 C10 1.448(6) . ?
C7A C8A 1.397(6) . ?
C7A C10A 1.439(6) . ?
C8 C9 1.413(6) . ?
C8 H8 0.9300 . ?
C8A C9A 1.395(6) . ?
C8A H8A 0.9300 . ?
C10 C11 1.188(7) . ?
C10A C11A 1.204(7) . ?
C11 Si1 1.851(5) . ?
C11A Si2 1.841(4) . ?
C12 Si1 1.860(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12A Si2 1.851(6) . ?
C12A H12D 0.9600 . ?
C12A H12E 0.9600 . ?
C12A H12F 0.9600 . ?
C13 Si1 1.855(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13A Si2 1.861(5) . ?
C13A H13D 0.9600 . ?
C13A H13E 0.9600 . ?
C13A H13F 0.9600 . ?
C14 Si1 1.858(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14A Si2 1.865(6) . ?
C14A H14D 0.9600 . ?
C14A H14E 0.9600 . ?
C14A H14F 0.9600 . ?
C15 N1 1.468(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C15A N1A 1.486(5) . ?
C15A H15D 0.9600 . ?
C15A H15E 0.9600 . ?
C15A H15F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C9 121.8(4) . . ?
C2 C1 Br1 118.6(3) . . ?
C9 C1 Br1 119.5(3) . . ?
C2A C1A C9A 122.0(4) . . ?
C2A C1A Br1A 117.7(3) . . ?
C9A C1A Br1A 120.3(3) . . ?
C1 C2 N1 121.4(4) . . ?
C1 C2 H2 119.3 . . ?
N1 C2 H2 119.3 . . ?
C1A C2A N1A 120.1(4) . . ?
C1A C2A H2A 119.9 . . ?
N1A C2A H2A 119.9 . . ?
O1 C3 N1 121.4(4) . . ?
O1 C3 C4 123.2(4) . . ?
N1 C3 C4 115.4(4) . . ?
O1A C3A N1A 120.9(4) . . ?
O1A C3A C4A 123.5(4) . . ?
N1A C3A C4A 115.6(4) . . ?
C5 C4 C9 120.8(4) . . ?
C5 C4 C3 118.0(4) . . ?
C9 C4 C3 121.1(4) . . ?
C5A C4A C9A 119.7(4) . . ?
C5A C4A C3A 118.9(4) . . ?
C9A C4A C3A 121.4(4) . . ?
C6 C5 C4 119.8(4) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C6A C5A C4A 120.5(4) . . ?
C6A C5A H5A 119.7 . . ?
C4A C5A H5A 119.7 . . ?
C5 C6 C7 120.2(4) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C5A C6A C7A 120.2(4) . . ?
C5A C6A H6A 119.9 . . ?
C7A C6A H6A 119.9 . . ?
C8 C7 C6 120.3(4) . . ?
C8 C7 C10 119.5(4) . . ?
C6 C7 C10 120.1(4) . . ?
C8A C7A C6A 119.6(4) . . ?
C8A C7A C10A 119.8(4) . . ?
C6A C7A C10A 120.5(4) . . ?
C7 C8 C9 119.4(4) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C9A C8A C7A 120.7(4) . . ?
C9A C8A H8A 119.7 . . ?
C7A C8A H8A 119.7 . . ?
C4 C9 C8 119.3(4) . . ?
C4 C9 C1 116.8(4) . . ?
C8 C9 C1 123.9(4) . . ?
C8A C9A C4A 119.3(4) . . ?
C8A C9A C1A 124.1(4) . . ?
C4A C9A C1A 116.5(4) . . ?
C11 C10 C7 176.8(4) . . ?
C11A C10A C7A 179.7(6) . . ?
C10 C11 Si1 174.3(4) . . ?
C10A C11A Si2 173.5(4) . . ?
Si1 C12 H12A 109.5 . . ?
Si1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
Si1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Si2 C12A H12D 109.5 . . ?
Si2 C12A H12E 109.5 . . ?
H12D C12A H12E 109.5 . . ?
Si2 C12A H12F 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
Si1 C13 H13A 109.5 . . ?
Si1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
Si1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Si2 C13A H13D 109.5 . . ?
Si2 C13A H13E 109.5 . . ?
H13D C13A H13E 109.5 . . ?
Si2 C13A H13F 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
Si1 C14 H14A 109.5 . . ?
Si1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
Si1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
Si2 C14A H14D 109.5 . . ?
Si2 C14A H14E 109.5 . . ?
H14D C14A H14E 109.5 . . ?
Si2 C14A H14F 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1A C15A H15D 109.5 . . ?
N1A C15A H15E 109.5 . . ?
H15D C15A H15E 109.5 . . ?
N1A C15A H15F 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?
C2 N1 C3 123.4(4) . . ?
C2 N1 C15 119.7(4) . . ?
C3 N1 C15 116.9(4) . . ?
C3A N1A C2A 124.2(4) . . ?
C3A N1A C15A 117.8(4) . . ?
C2A N1A C15A 118.0(4) . . ?
C11 Si1 C13 108.5(2) . . ?
C11 Si1 C14 109.4(2) . . ?
C13 Si1 C14 109.1(3) . . ?
C11 Si1 C12 107.8(2) . . ?
C13 Si1 C12 111.2(3) . . ?
C14 Si1 C12 110.7(2) . . ?
C11A Si2 C12A 110.7(2) . . ?
C11A Si2 C13A 106.7(2) . . ?
C12A Si2 C13A 109.8(3) . . ?
C11A Si2 C14A 107.3(2) . . ?
C12A Si2 C14A 111.2(3) . . ?
C13A Si2 C14A 111.1(3) . . ?

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
C9 C1 C2 N1 1.6(6) . . . . ?
Br1 C1 C2 N1 178.3(3) . . . . ?
C9A C1A C2A N1A 0.8(6) . . . . ?
Br1A C1A C2A N1A 179.9(3) . . . . ?
O1 C3 C4 C5 2.6(6) . . . . ?
N1 C3 C4 C5 -176.7(4) . . . . ?
O1 C3 C4 C9 -178.2(4) . . . . ?
N1 C3 C4 C9 2.5(6) . . . . ?
O1A C3A C4A C5A 1.9(6) . . . . ?
N1A C3A C4A C5A -176.5(4) . . . . ?
O1A C3A C4A C9A -178.3(4) . . . . ?
N1A C3A C4A C9A 3.2(6) . . . . ?
C9 C4 C5 C6 0.3(7) . . . . ?
C3 C4 C5 C6 179.5(4) . . . . ?
C9A C4A C5A C6A -1.3(7) . . . . ?
C3A C4A C5A C6A 178.4(4) . . . . ?
C4 C5 C6 C7 1.2(7) . . . . ?
C4A C5A C6A C7A 0.5(7) . . . . ?
C5 C6 C7 C8 -0.4(7) . . . . ?
C5 C6 C7 C10 -177.6(4) . . . . ?
C5A C6A C7A C8A 0.7(7) . . . . ?
C5A C6A C7A C10A -178.0(4) . . . . ?
C6 C7 C8 C9 -1.8(6) . . . . ?
C10 C7 C8 C9 175.3(4) . . . . ?
C6A C7A C8A C9A -1.0(6) . . . . ?
C10A C7A C8A C9A 177.6(4) . . . . ?
C5 C4 C9 C8 -2.6(6) . . . . ?
C3 C4 C9 C8 178.2(4) . . . . ?
C5 C4 C9 C1 176.1(4) . . . . ?
C3 C4 C9 C1 -3.2(6) . . . . ?
C7 C8 C9 C4 3.3(6) . . . . ?
C7 C8 C9 C1 -175.2(4) . . . . ?
C2 C1 C9 C4 1.1(6) . . . . ?
Br1 C1 C9 C4 -175.6(3) . . . . ?
C2 C1 C9 C8 179.7(4) . . . . ?
Br1 C1 C9 C8 3.0(5) . . . . ?
C7A C8A C9A C4A 0.2(6) . . . . ?
C7A C8A C9A C1A -179.2(4) . . . . ?
C5A C4A C9A C8A 1.0(6) . . . . ?
C3A C4A C9A C8A -178.7(4) . . . . ?
C5A C4A C9A C1A -179.6(4) . . . . ?
C3A C4A C9A C1A 0.7(6) . . . . ?
C2A C1A C9A C8A 176.6(4) . . . . ?
Br1A C1A C9A C8A -2.4(6) . . . . ?
C2A C1A C9A C4A -2.8(6) . . . . ?
Br1A C1A C9A C4A 178.2(3) . . . . ?
C1 C2 N1 C3 -2.3(6) . . . . ?
C1 C2 N1 C15 178.4(4) . . . . ?
O1 C3 N1 C2 -179.1(4) . . . . ?
C4 C3 N1 C2 0.2(6) . . . . ?
O1 C3 N1 C15 0.3(6) . . . . ?
C4 C3 N1 C15 179.5(4) . . . . ?
O1A C3A N1A C2A 176.0(4) . . . . ?
C4A C3A N1A C2A -5.5(6) . . . . ?
O1A C3A N1A C15A -3.2(6) . . . . ?
C4A C3A N1A C15A 175.3(4) . . . . ?
C1A C2A N1A C3A 3.7(6) . . . . ?
C1A C2A N1A C15A -177.1(4) . . . . ?

_refine_diff_density_max         1.178
_refine_diff_density_min         -1.631
_refine_diff_density_rms         0.179

####################################################################### 
# 
# 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_CMPD16SiMe3
_audit_block_doi                 10.5517/ccdc.csd.cc2cyfc4
_database_code_depnum_ccdc_archive 'CCDC 2203026'
loop_
_audit_author_name
_audit_author_address
'Jonathan White'
;University of Melbourne
Australia
;
_audit_update_record             
;
2022-08-23 deposited with the CCDC.	2023-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C53 H58 N2 O8 S2 Si2'
_chemical_formula_weight         971.31
_chemical_oxdiff_usercomment     "From Catherine's suzuki reaction THIN NEEDLE"

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   7.5225(2)
_cell_length_b                   17.1489(4)
_cell_length_c                   19.5229(4)
_cell_angle_alpha                89.986(2)
_cell_angle_beta                 88.363(2)
_cell_angle_gamma                89.925(2)
_cell_volume                     2517.47(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    8028
_cell_measurement_theta_min      2.2600
_cell_measurement_theta_max      76.7840

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             1028
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.038
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.864
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.640
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.425
_oxdiff_exptl_absorpt_empirical_full_max 4.617
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44069
_diffrn_reflns_av_unetI/netI     0.1026
_diffrn_reflns_av_R_equivalents  0.1267
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.264
_diffrn_reflns_theta_max         78.301
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10604
_reflns_number_gt                7513
_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 1.171.40.68a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1292P)²+0.3705P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10604
_refine_ls_number_parameters     617
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0736
_refine_ls_wR_factor_ref         0.2150
_refine_ls_wR_factor_gt          0.1879
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
C1 C 0.1572(4) 0.11823(16) 0.80383(15) 0.0249(6) Uani 1 1 d . . . . .
C2 C 0.0824(4) 0.05068(17) 0.78489(15) 0.0264(6) Uani 1 1 d . . . . .
H2 H 0.086125 0.008779 0.815067 0.032 Uiso 1 1 calc R U . . .
C3 C -0.0014(4) 0.09686(17) 0.67354(16) 0.0266(6) Uani 1 1 d . . . . .
C4 C 0.0702(4) 0.17309(17) 0.69331(16) 0.0272(6) Uani 1 1 d . . . . .
C5 C 0.1499(4) 0.18353(16) 0.75699(16) 0.0256(6) Uani 1 1 d . . . . .
C6 C 0.2107(4) 0.25791(17) 0.77437(17) 0.0292(6) Uani 1 1 d . . . . .
H6 H 0.264146 0.265464 0.816208 0.035 Uiso 1 1 calc R U . . .
C7 C 0.1922(4) 0.32054(17) 0.73004(17) 0.0309(6) Uani 1 1 d . . . . .
C8 C 0.1171(5) 0.30879(19) 0.66561(18) 0.0345(7) Uani 1 1 d . . . . .
H8 H 0.106812 0.350358 0.635362 0.041 Uiso 1 1 calc R U . . .
C9 C 0.0587(4) 0.23581(18) 0.64735(17) 0.0308(6) Uani 1 1 d . . . . .
H9 H 0.011450 0.228015 0.604387 0.037 Uiso 1 1 calc R U . . .
C10 C 0.2378(4) 0.12143(16) 0.87226(16) 0.0256(6) Uani 1 1 d . . . . .
C11 C 0.4230(4) 0.12603(16) 0.87885(16) 0.0279(6) Uani 1 1 d . . . . .
C12 C 0.5006(4) 0.11772(19) 0.94251(17) 0.0325(7) Uani 1 1 d . . . . .
H12 H 0.623660 0.118869 0.945860 0.039 Uiso 1 1 calc R U . . .
C13 C 0.3938(4) 0.10780(19) 1.00040(17) 0.0325(7) Uani 1 1 d . . . . .
H13 H 0.444429 0.101746 1.042991 0.039 Uiso 1 1 calc R U . . .
C14 C 0.2100(5) 0.10689(18) 0.99474(17) 0.0316(7) Uani 1 1 d . . . . .
C15 C 0.1320(4) 0.11280(17) 0.93141(16) 0.0271(6) Uani 1 1 d . . . . .
H15 H 0.008884 0.110986 0.928490 0.033 Uiso 1 1 calc R U . . .
C16 C 0.2383(5) 0.39713(18) 0.75397(19) 0.0352(7) Uani 1 1 d . . . . .
C17 C 0.2690(6) 0.4593(2) 0.7797(2) 0.0425(8) Uani 1 1 d . . . . .
C18 C 0.1504(7) 0.6248(2) 0.7958(3) 0.0645(14) Uani 1 1 d . . . . .
H18A H 0.183940 0.633074 0.748575 0.097 Uiso 1 1 calc R U . . .
H18B H 0.164176 0.672467 0.820849 0.097 Uiso 1 1 calc R U . . .
H18C H 0.028503 0.608351 0.799166 0.097 Uiso 1 1 calc R U . . .
C19 C 0.5322(7) 0.5791(2) 0.8284(3) 0.0550(11) Uani 1 1 d . . . . .
H19A H 0.604824 0.538016 0.845896 0.082 Uiso 1 1 calc R U . . .
H19B H 0.546499 0.625196 0.855653 0.082 Uiso 1 1 calc R U . . .
H19C H 0.567716 0.589973 0.781776 0.082 Uiso 1 1 calc R U . . .
C20 C 0.2208(11) 0.5232(3) 0.9209(3) 0.0809(18) Uani 1 1 d . . . . .
H20A H 0.100432 0.504692 0.920941 0.121 Uiso 1 1 calc R U . . .
H20B H 0.227221 0.568691 0.949460 0.121 Uiso 1 1 calc R U . . .
H20C H 0.296694 0.483270 0.938366 0.121 Uiso 1 1 calc R U . . .
C21 C 0.7054(5) 0.1444(2) 0.82312(19) 0.0373(7) Uani 1 1 d . . . . .
H21A H 0.755430 0.155936 0.778470 0.056 Uiso 1 1 calc R U . . .
H21B H 0.755288 0.096672 0.839623 0.056 Uiso 1 1 calc R U . . .
H21C H 0.732108 0.186097 0.853993 0.056 Uiso 1 1 calc R U . . .
C22 C 0.0753(6) 0.1917(2) 1.1066(2) 0.0463(9) Uani 1 1 d . . . . .
H22A H 0.195736 0.208392 1.112374 0.069 Uiso 1 1 calc R U . . .
H22B H 0.014295 0.189993 1.150431 0.069 Uiso 1 1 calc R U . . .
H22C H 0.016088 0.227781 1.077290 0.069 Uiso 1 1 calc R U . . .
C24 C -0.0761(5) -0.03578(19) 0.70784(18) 0.0380(8) Uani 1 1 d . . . . .
H24A H -0.006769 -0.060182 0.671768 0.057 Uiso 1 1 calc R U . . .
H24B H -0.195959 -0.028747 0.693362 0.057 Uiso 1 1 calc R U . . .
H24C H -0.076161 -0.068211 0.747922 0.057 Uiso 1 1 calc R U . . .
C25 C 0.3304(4) 0.12720(16) 0.46408(15) 0.0233(6) Uani 1 1 d . . . . .
C26 C 0.2756(4) 0.05209(16) 0.47038(15) 0.0251(6) Uani 1 1 d . . . . .
H26 H 0.230808 0.027256 0.432213 0.030 Uiso 1 1 calc R U . . .
C27 C 0.3505(4) 0.04206(16) 0.58948(15) 0.0250(6) Uani 1 1 d . . . . .
C28 C 0.4179(4) 0.12229(16) 0.58363(15) 0.0249(6) Uani 1 1 d . . . . .
C29 C 0.4041(4) 0.16484(16) 0.52220(16) 0.0251(6) Uani 1 1 d . . . . .
C30 C 0.4663(4) 0.24240(16) 0.52086(16) 0.0270(6) Uani 1 1 d . . . . .
H30 H 0.456201 0.271765 0.481106 0.032 Uiso 1 1 calc R U . . .
C31 C 0.5420(4) 0.27555(17) 0.57759(17) 0.0297(6) Uani 1 1 d . . . . .
C32 C 0.5575(4) 0.23177(18) 0.63852(17) 0.0303(6) Uani 1 1 d . . . . .
H32 H 0.608619 0.253831 0.676758 0.036 Uiso 1 1 calc R U . . .
C33 C 0.4962(4) 0.15600(17) 0.64067(17) 0.0287(6) Uani 1 1 d . . . . .
H33 H 0.506940 0.126927 0.680562 0.034 Uiso 1 1 calc R U . . .
C34 C 0.3151(4) 0.16734(15) 0.39624(15) 0.0236(6) Uani 1 1 d . . . . .
C35 C 0.1695(4) 0.21579(16) 0.38290(16) 0.0263(6) Uani 1 1 d . . . . .
C36 C 0.1503(4) 0.24990(16) 0.31827(17) 0.0278(6) Uani 1 1 d . . . . .
H36 H 0.052367 0.281198 0.309659 0.033 Uiso 1 1 calc R U . . .
C37 C 0.2790(4) 0.23648(16) 0.26726(16) 0.0277(6) Uani 1 1 d . . . . .
H37 H 0.268221 0.259339 0.224372 0.033 Uiso 1 1 calc R U . . .
C38 C 0.4231(4) 0.18922(15) 0.28011(16) 0.0264(6) Uani 1 1 d . . . . .
C39 C 0.4416(4) 0.15462(16) 0.34429(16) 0.0249(6) Uani 1 1 d . . . . .
H39 H 0.539213 0.122884 0.352266 0.030 Uiso 1 1 calc R U . . .
C40 C 0.6024(5) 0.35544(19) 0.57642(18) 0.0351(7) Uani 1 1 d . . . . .
C41 C 0.6469(5) 0.4231(2) 0.5774(2) 0.0405(8) Uani 1 1 d . . . . .
C42 C 0.4903(6) 0.5765(2) 0.6194(2) 0.0469(9) Uani 1 1 d . . . . .
H42A H 0.412023 0.578302 0.581439 0.070 Uiso 1 1 calc R U . . .
H42B H 0.516216 0.628597 0.633957 0.070 Uiso 1 1 calc R U . . .
H42C H 0.434005 0.548360 0.656603 0.070 Uiso 1 1 calc R U . . .
C43 C 0.8658(7) 0.5261(2) 0.6620(3) 0.0589(12) Uani 1 1 d . . . . .
H43A H 0.822183 0.494454 0.699394 0.088 Uiso 1 1 calc R U . . .
H43B H 0.883150 0.578536 0.677796 0.088 Uiso 1 1 calc R U . . .
H43C H 0.976831 0.505425 0.644721 0.088 Uiso 1 1 calc R U . . .
C44 C 0.7941(6) 0.5725(2) 0.5133(2) 0.0478(9) Uani 1 1 d . . . . .
H44A H 0.908479 0.550270 0.502137 0.072 Uiso 1 1 calc R U . . .
H44B H 0.806530 0.627577 0.520614 0.072 Uiso 1 1 calc R U . . .
H44C H 0.715366 0.563612 0.476321 0.072 Uiso 1 1 calc R U . . .
C45 C -0.1089(5) 0.2673(2) 0.4228(2) 0.0398(8) Uani 1 1 d . . . . .
H45A H -0.168862 0.243790 0.385322 0.060 Uiso 1 1 calc R U . . .
H45B H -0.079804 0.320367 0.411542 0.060 Uiso 1 1 calc R U . . .
H45C H -0.185124 0.266246 0.463085 0.060 Uiso 1 1 calc R U . . .
C46 C 0.5480(5) 0.06788(18) 0.19659(17) 0.0327(7) Uani 1 1 d . . . . .
H46A H 0.572702 0.037730 0.236656 0.049 Uiso 1 1 calc R U . . .
H46B H 0.626324 0.051985 0.159486 0.049 Uiso 1 1 calc R U . . .
H46C H 0.426908 0.059628 0.184149 0.049 Uiso 1 1 calc R U . . .
C47 C 0.2069(4) -0.06764(16) 0.53437(16) 0.0270(6) Uani 1 1 d . . . . .
H47A H 0.105607 -0.067665 0.565394 0.041 Uiso 1 1 calc R U . . .
H47B H 0.294458 -0.103584 0.550374 0.041 Uiso 1 1 calc R U . . .
H47C H 0.170789 -0.083116 0.489617 0.041 Uiso 1 1 calc R U . . .
C48 C 0.5684(6) 0.3200(2) 0.9539(2) 0.0463(9) Uani 1 1 d . . . . .
C49 C 0.5818(7) 0.3565(2) 0.8913(3) 0.0555(11) Uani 1 1 d . . . . .
H49 H 0.479820 0.373363 0.869873 0.067 Uiso 1 1 calc R U . . .
C50 C 0.7487(9) 0.3682(3) 0.8599(3) 0.0672(14) Uani 1 1 d . . . . .
H50 H 0.757295 0.392703 0.817480 0.081 Uiso 1 1 calc R U . . .
C51 C 0.8986(7) 0.3441(3) 0.8909(3) 0.0620(12) Uani 1 1 d . . . . .
H51 H 1.009838 0.354985 0.871173 0.074 Uiso 1 1 calc R U . . .
C52 C 0.8849(7) 0.3037(3) 0.9516(3) 0.0588(11) Uani 1 1 d . . . . .
H52 H 0.986574 0.284334 0.971738 0.071 Uiso 1 1 calc R U . . .
C53 C 0.7193(6) 0.2917(2) 0.9829(2) 0.0508(10) Uani 1 1 d . . . . .
H53 H 0.710526 0.264211 1.023909 0.061 Uiso 1 1 calc R U . . .
C54 C 0.3917(7) 0.3088(3) 0.9900(3) 0.0636(12) Uani 1 1 d . . . . .
H54A H 0.337218 0.358715 0.998301 0.095 Uiso 1 1 calc R U . . .
H54B H 0.408391 0.282720 1.032821 0.095 Uiso 1 1 calc R U . . .
H54C H 0.316378 0.277899 0.961906 0.095 Uiso 1 1 calc R U . . .
N1 N 0.0009(4) 0.04005(14) 0.72375(13) 0.0276(5) Uani 1 1 d . . . . .
N2 N 0.2834(3) 0.01111(13) 0.53088(13) 0.0244(5) Uani 1 1 d . . . . .
O1 O -0.0646(3) 0.08297(13) 0.61721(12) 0.0334(5) Uani 1 1 d . . . . .
O2 O 0.5164(3) 0.13639(13) 0.81903(12) 0.0314(5) Uani 1 1 d . . . . .
O3 O -0.1037(3) 0.08020(15) 1.05109(13) 0.0400(6) Uani 1 1 d . . . . .
O4 O 0.1637(4) 0.04725(17) 1.11572(14) 0.0472(7) Uani 1 1 d . . . . .
O5 O 0.3502(3) 0.00436(11) 0.64345(11) 0.0282(5) Uani 1 1 d . . . . .
O6 O 0.0493(3) 0.22532(12) 0.43535(12) 0.0325(5) Uani 1 1 d . . . . .
O7 O 0.7568(3) 0.17594(14) 0.23986(12) 0.0369(5) Uani 1 1 d . . . . .
O8 O 0.5347(4) 0.21199(13) 0.15415(12) 0.0358(5) Uani 1 1 d . . . . .
Si1 Si 0.29417(17) 0.54849(6) 0.83224(6) 0.0474(3) Uani 1 1 d . . . . .
Si2 Si 0.70132(14) 0.52621(5) 0.59261(6) 0.0395(2) Uani 1 1 d . . . . .
S1 S 0.07495(11) 0.09858(5) 1.06947(4) 0.0351(2) Uani 1 1 d . . . . .
S2 S 0.58100(10) 0.16732(4) 0.21395(4) 0.02794(19) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.345(4) . ?
C1 C5 1.448(4) . ?
C1 C10 1.484(5) . ?
C2 N1 1.369(4) . ?
C2 H2 0.9300 . ?
C3 O1 1.234(4) . ?
C3 N1 1.382(4) . ?
C3 C4 1.470(4) . ?
C4 C9 1.405(4) . ?
C4 C5 1.407(5) . ?
C5 C6 1.401(4) . ?
C6 C7 1.388(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.408(5) . ?
C7 C16 1.440(4) . ?
C8 C9 1.377(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C15 1.392(4) . ?
C10 C11 1.405(4) . ?
C11 O2 1.357(4) . ?
C11 C12 1.395(5) . ?
C12 C13 1.378(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.390(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.387(5) . ?
C14 S1 1.760(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.204(5) . ?
C17 Si1 1.855(4) . ?
C18 Si1 1.851(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 Si1 1.866(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 Si1 1.854(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 O2 1.433(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 S1 1.754(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C24 N1 1.461(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.357(4) . ?
C25 C29 1.432(4) . ?
C25 C34 1.500(4) . ?
C26 N2 1.377(4) . ?
C26 H26 0.9300 . ?
C27 O5 1.236(4) . ?
C27 N2 1.371(4) . ?
C27 C28 1.470(4) . ?
C28 C33 1.400(5) . ?
C28 C29 1.410(4) . ?
C29 C30 1.410(4) . ?
C30 C31 1.382(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.414(5) . ?
C31 C40 1.444(4) . ?
C32 C33 1.380(4) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C34 C39 1.388(4) . ?
C34 C35 1.404(4) . ?
C35 O6 1.356(4) . ?
C35 C36 1.402(5) . ?
C36 C37 1.388(5) . ?
C36 H36 0.9300 . ?
C37 C38 1.381(4) . ?
C37 H37 0.9300 . ?
C38 C39 1.397(4) . ?
C38 S2 1.770(3) . ?
C39 H39 0.9300 . ?
C40 C41 1.209(5) . ?
C41 Si2 1.841(4) . ?
C42 Si2 1.867(4) . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 Si2 1.861(5) . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 Si2 1.858(4) . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C45 O6 1.417(4) . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C46 S2 1.758(3) . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C47 N2 1.469(4) . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C48 C53 1.371(6) . ?
C48 C49 1.374(7) . ?
C48 C54 1.499(7) . ?
C49 C50 1.396(8) . ?
C49 H49 0.9300 . ?
C50 C51 1.359(8) . ?
C50 H50 0.9300 . ?
C51 C52 1.375(8) . ?
C51 H51 0.9300 . ?
C52 C53 1.387(7) . ?
C52 H52 0.9300 . ?
C53 H53 0.9300 . ?
C54 H54A 0.9600 . ?
C54 H54B 0.9600 . ?
C54 H54C 0.9600 . ?
O3 S1 1.436(3) . ?
O4 S1 1.438(3) . ?
O7 S2 1.437(3) . ?
O8 S2 1.447(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
C2 C1 C5 118.0(3) . . ?
C2 C1 C10 117.7(3) . . ?
C5 C1 C10 124.3(3) . . ?
C1 C2 N1 123.8(3) . . ?
C1 C2 H2 118.1 . . ?
N1 C2 H2 118.1 . . ?
O1 C3 N1 120.6(3) . . ?
O1 C3 C4 124.0(3) . . ?
N1 C3 C4 115.4(3) . . ?
C9 C4 C5 120.1(3) . . ?
C9 C4 C3 118.9(3) . . ?
C5 C4 C3 121.0(3) . . ?
C6 C5 C4 118.7(3) . . ?
C6 C5 C1 122.2(3) . . ?
C4 C5 C1 118.9(3) . . ?
C7 C6 C5 121.0(3) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 119.7(3) . . ?
C6 C7 C16 118.3(3) . . ?
C8 C7 C16 121.8(3) . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C4 120.3(3) . . ?
C8 C9 H9 119.8 . . ?
C4 C9 H9 119.8 . . ?
C15 C10 C11 118.4(3) . . ?
C15 C10 C1 120.3(3) . . ?
C11 C10 C1 121.1(3) . . ?
O2 C11 C12 124.1(3) . . ?
O2 C11 C10 114.8(3) . . ?
C12 C11 C10 121.1(3) . . ?
C13 C12 C11 119.6(3) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 119.6(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 121.1(3) . . ?
C15 C14 S1 119.7(3) . . ?
C13 C14 S1 119.2(3) . . ?
C14 C15 C10 120.0(3) . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
C17 C16 C7 173.9(4) . . ?
C16 C17 Si1 170.1(4) . . ?
Si1 C18 H18A 109.5 . . ?
Si1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
Si1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
Si1 C19 H19A 109.5 . . ?
Si1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
Si1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
Si1 C20 H20A 109.5 . . ?
Si1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
Si1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
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 . . ?
S1 C22 H22A 109.5 . . ?
S1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
S1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N1 C24 H24A 109.5 . . ?
N1 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N1 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C29 118.7(3) . . ?
C26 C25 C34 119.0(3) . . ?
C29 C25 C34 122.3(2) . . ?
C25 C26 N2 122.8(3) . . ?
C25 C26 H26 118.6 . . ?
N2 C26 H26 118.6 . . ?
O5 C27 N2 121.1(3) . . ?
O5 C27 C28 123.2(3) . . ?
N2 C27 C28 115.6(3) . . ?
C33 C28 C29 120.4(3) . . ?
C33 C28 C27 118.5(3) . . ?
C29 C28 C27 121.1(3) . . ?
C30 C29 C28 118.1(3) . . ?
C30 C29 C25 123.2(3) . . ?
C28 C29 C25 118.7(3) . . ?
C31 C30 C29 121.2(3) . . ?
C31 C30 H30 119.4 . . ?
C29 C30 H30 119.4 . . ?
C30 C31 C32 120.1(3) . . ?
C30 C31 C40 121.0(3) . . ?
C32 C31 C40 118.9(3) . . ?
C33 C32 C31 119.3(3) . . ?
C33 C32 H32 120.3 . . ?
C31 C32 H32 120.3 . . ?
C32 C33 C28 120.9(3) . . ?
C32 C33 H33 119.6 . . ?
C28 C33 H33 119.6 . . ?
C39 C34 C35 118.6(3) . . ?
C39 C34 C25 120.3(3) . . ?
C35 C34 C25 121.0(3) . . ?
O6 C35 C36 123.1(3) . . ?
O6 C35 C34 115.9(3) . . ?
C36 C35 C34 120.9(3) . . ?
C37 C36 C35 119.3(3) . . ?
C37 C36 H36 120.4 . . ?
C35 C36 H36 120.4 . . ?
C38 C37 C36 120.1(3) . . ?
C38 C37 H37 120.0 . . ?
C36 C37 H37 120.0 . . ?
C37 C38 C39 120.7(3) . . ?
C37 C38 S2 120.3(2) . . ?
C39 C38 S2 118.9(2) . . ?
C34 C39 C38 120.3(3) . . ?
C34 C39 H39 119.8 . . ?
C38 C39 H39 119.8 . . ?
C41 C40 C31 177.1(4) . . ?
C40 C41 Si2 171.2(4) . . ?
Si2 C42 H42A 109.5 . . ?
Si2 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
Si2 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
Si2 C43 H43A 109.5 . . ?
Si2 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
Si2 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
Si2 C44 H44A 109.5 . . ?
Si2 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
Si2 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
O6 C45 H45A 109.5 . . ?
O6 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
O6 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
S2 C46 H46A 109.5 . . ?
S2 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
S2 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
N2 C47 H47A 109.5 . . ?
N2 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
N2 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C53 C48 C49 119.2(4) . . ?
C53 C48 C54 119.6(4) . . ?
C49 C48 C54 121.2(4) . . ?
C48 C49 C50 119.9(5) . . ?
C48 C49 H49 120.1 . . ?
C50 C49 H49 120.1 . . ?
C51 C50 C49 120.6(4) . . ?
C51 C50 H50 119.7 . . ?
C49 C50 H50 119.7 . . ?
C50 C51 C52 119.6(5) . . ?
C50 C51 H51 120.2 . . ?
C52 C51 H51 120.2 . . ?
C51 C52 C53 119.9(5) . . ?
C51 C52 H52 120.0 . . ?
C53 C52 H52 120.0 . . ?
C48 C53 C52 120.7(4) . . ?
C48 C53 H53 119.7 . . ?
C52 C53 H53 119.7 . . ?
C48 C54 H54A 109.5 . . ?
C48 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C48 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C2 N1 C3 122.6(2) . . ?
C2 N1 C24 119.6(3) . . ?
C3 N1 C24 117.6(3) . . ?
C27 N2 C26 122.9(2) . . ?
C27 N2 C47 118.1(2) . . ?
C26 N2 C47 118.8(3) . . ?
C11 O2 C21 117.1(3) . . ?
C35 O6 C45 118.4(3) . . ?
C18 Si1 C20 111.2(3) . . ?
C18 Si1 C17 107.5(2) . . ?
C20 Si1 C17 106.9(2) . . ?
C18 Si1 C19 110.8(2) . . ?
C20 Si1 C19 111.3(3) . . ?
C17 Si1 C19 108.9(2) . . ?
C41 Si2 C44 110.88(19) . . ?
C41 Si2 C43 105.86(17) . . ?
C44 Si2 C43 111.4(2) . . ?
C41 Si2 C42 107.25(19) . . ?
C44 Si2 C42 109.43(18) . . ?
C43 Si2 C42 111.9(2) . . ?
O3 S1 O4 118.45(15) . . ?
O3 S1 C22 108.47(19) . . ?
O4 S1 C22 106.9(2) . . ?
O3 S1 C14 109.46(15) . . ?
O4 S1 C14 107.63(17) . . ?
C22 S1 C14 105.10(17) . . ?
O7 S2 O8 118.29(14) . . ?
O7 S2 C46 107.78(16) . . ?
O8 S2 C46 108.61(16) . . ?
O7 S2 C38 109.04(15) . . ?
O8 S2 C38 107.78(14) . . ?
C46 S2 C38 104.50(14) . . ?

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
C5 C1 C2 N1 0.5(4) . . . . ?
C10 C1 C2 N1 178.9(3) . . . . ?
O1 C3 C4 C9 3.5(5) . . . . ?
N1 C3 C4 C9 -174.6(3) . . . . ?
O1 C3 C4 C5 -176.2(3) . . . . ?
N1 C3 C4 C5 5.7(4) . . . . ?
C9 C4 C5 C6 2.4(4) . . . . ?
C3 C4 C5 C6 -177.9(3) . . . . ?
C9 C4 C5 C1 179.0(3) . . . . ?
C3 C4 C5 C1 -1.3(4) . . . . ?
C2 C1 C5 C6 174.6(3) . . . . ?
C10 C1 C5 C6 -3.7(5) . . . . ?
C2 C1 C5 C4 -1.9(4) . . . . ?
C10 C1 C5 C4 179.8(3) . . . . ?
C4 C5 C6 C7 0.3(5) . . . . ?
C1 C5 C6 C7 -176.1(3) . . . . ?
C5 C6 C7 C8 -2.2(5) . . . . ?
C5 C6 C7 C16 172.9(3) . . . . ?
C6 C7 C8 C9 1.4(5) . . . . ?
C16 C7 C8 C9 -173.6(3) . . . . ?
C7 C8 C9 C4 1.4(5) . . . . ?
C5 C4 C9 C8 -3.3(5) . . . . ?
C3 C4 C9 C8 177.0(3) . . . . ?
C2 C1 C10 C15 -64.2(4) . . . . ?
C5 C1 C10 C15 114.1(3) . . . . ?
C2 C1 C10 C11 109.9(3) . . . . ?
C5 C1 C10 C11 -71.7(4) . . . . ?
C15 C10 C11 O2 -178.4(2) . . . . ?
C1 C10 C11 O2 7.3(4) . . . . ?
C15 C10 C11 C12 3.6(4) . . . . ?
C1 C10 C11 C12 -170.6(3) . . . . ?
O2 C11 C12 C13 179.7(3) . . . . ?
C10 C11 C12 C13 -2.5(5) . . . . ?
C11 C12 C13 C14 -0.6(5) . . . . ?
C12 C13 C14 C15 2.5(5) . . . . ?
C12 C13 C14 S1 -177.2(2) . . . . ?
C13 C14 C15 C10 -1.4(5) . . . . ?
S1 C14 C15 C10 178.3(2) . . . . ?
C11 C10 C15 C14 -1.7(4) . . . . ?
C1 C10 C15 C14 172.6(3) . . . . ?
C29 C25 C26 N2 1.8(4) . . . . ?
C34 C25 C26 N2 -179.4(3) . . . . ?
O5 C27 C28 C33 4.3(4) . . . . ?
N2 C27 C28 C33 -176.9(3) . . . . ?
O5 C27 C28 C29 -175.6(3) . . . . ?
N2 C27 C28 C29 3.3(4) . . . . ?
C33 C28 C29 C30 -1.9(4) . . . . ?
C27 C28 C29 C30 178.0(3) . . . . ?
C33 C28 C29 C25 177.3(3) . . . . ?
C27 C28 C29 C25 -2.9(4) . . . . ?
C26 C25 C29 C30 179.4(3) . . . . ?
C34 C25 C29 C30 0.7(4) . . . . ?
C26 C25 C29 C28 0.3(4) . . . . ?
C34 C25 C29 C28 -178.4(3) . . . . ?
C28 C29 C30 C31 1.3(4) . . . . ?
C25 C29 C30 C31 -177.8(3) . . . . ?
C29 C30 C31 C32 -0.3(5) . . . . ?
C29 C30 C31 C40 -178.8(3) . . . . ?
C30 C31 C32 C33 -0.1(5) . . . . ?
C40 C31 C32 C33 178.4(3) . . . . ?
C31 C32 C33 C28 -0.5(5) . . . . ?
C29 C28 C33 C32 1.5(5) . . . . ?
C27 C28 C33 C32 -178.4(3) . . . . ?
C26 C25 C34 C39 -80.3(4) . . . . ?
C29 C25 C34 C39 98.4(3) . . . . ?
C26 C25 C34 C35 97.0(3) . . . . ?
C29 C25 C34 C35 -84.2(4) . . . . ?
C39 C34 C35 O6 179.3(3) . . . . ?
C25 C34 C35 O6 1.9(4) . . . . ?
C39 C34 C35 C36 0.9(4) . . . . ?
C25 C34 C35 C36 -176.5(3) . . . . ?
O6 C35 C36 C37 -179.4(3) . . . . ?
C34 C35 C36 C37 -1.1(4) . . . . ?
C35 C36 C37 C38 0.7(4) . . . . ?
C36 C37 C38 C39 -0.2(4) . . . . ?
C36 C37 C38 S2 176.4(2) . . . . ?
C35 C34 C39 C38 -0.3(4) . . . . ?
C25 C34 C39 C38 177.1(3) . . . . ?
C37 C38 C39 C34 -0.1(4) . . . . ?
S2 C38 C39 C34 -176.6(2) . . . . ?
C53 C48 C49 C50 -3.6(7) . . . . ?
C54 C48 C49 C50 178.0(4) . . . . ?
C48 C49 C50 C51 -0.3(7) . . . . ?
C49 C50 C51 C52 4.0(8) . . . . ?
C50 C51 C52 C53 -3.8(7) . . . . ?
C49 C48 C53 C52 3.8(6) . . . . ?
C54 C48 C53 C52 -177.8(4) . . . . ?
C51 C52 C53 C48 -0.1(7) . . . . ?
C1 C2 N1 C3 4.4(5) . . . . ?
C1 C2 N1 C24 179.8(3) . . . . ?
O1 C3 N1 C2 174.6(3) . . . . ?
C4 C3 N1 C2 -7.2(4) . . . . ?
O1 C3 N1 C24 -0.9(4) . . . . ?
C4 C3 N1 C24 177.3(3) . . . . ?
O5 C27 N2 C26 177.7(3) . . . . ?
C28 C27 N2 C26 -1.2(4) . . . . ?
O5 C27 N2 C47 1.5(4) . . . . ?
C28 C27 N2 C47 -177.4(2) . . . . ?
C25 C26 N2 C27 -1.3(4) . . . . ?
C25 C26 N2 C47 174.8(3) . . . . ?
C12 C11 O2 C21 -4.4(4) . . . . ?
C10 C11 O2 C21 177.7(3) . . . . ?
C36 C35 O6 C45 4.4(4) . . . . ?
C34 C35 O6 C45 -173.9(3) . . . . ?
C15 C14 S1 O3 14.0(3) . . . . ?
C13 C14 S1 O3 -166.3(3) . . . . ?
C15 C14 S1 O4 144.0(3) . . . . ?
C13 C14 S1 O4 -36.3(3) . . . . ?
C15 C14 S1 C22 -102.3(3) . . . . ?
C13 C14 S1 C22 77.4(3) . . . . ?
C37 C38 S2 O7 134.6(2) . . . . ?
C39 C38 S2 O7 -48.8(3) . . . . ?
C37 C38 S2 O8 5.0(3) . . . . ?
C39 C38 S2 O8 -178.4(2) . . . . ?
C37 C38 S2 C46 -110.4(3) . . . . ?
C39 C38 S2 C46 66.2(3) . . . . ?

_refine_diff_density_max         0.854
_refine_diff_density_min         -0.656
_refine_diff_density_rms         0.098

