# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_pyn1817SNQ
_database_code_depnum_ccdc_archive 'CCDC 2010550'
loop_
_audit_author_name
_audit_author_address
'Anthony Willis'
;Australian National University
Australia
;
_audit_update_record             
;
2020-06-18 deposited with the CCDC.	2020-11-11 downloaded from the CCDC.
;
_audit_creation_date             18-09-05
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'Z:\pyn1817SNQ\Tony_pyn1817SNQ_da At 11:51 on'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   10.4037(1)
_cell_length_b                   10.6504(1)
_cell_length_c                   13.4206(1)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1487.05(2)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C17 H20 Cl1 N1 O2 
# Dc =      1.37 Fooo =    648.00 Mu =     23.03 M =    305.80
# Found Formula = C17 H20 Cl1 N1 O2 
# Dc =      1.37 FOOO =    648.00 Mu =     23.03 M =    305.80

_chemical_formula_sum            'C17 H20 Cl N O2'
_chemical_formula_moiety         'C17 H20 Cl N O2'
_chemical_compound_source        ' from U of Wollongong '
_chemical_formula_weight         305.80


_cell_measurement_reflns_used    28996
_cell_measurement_theta_min      5
_cell_measurement_theta_max      74
_cell_measurement_temperature    150

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.053
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_max          0.267

_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    2.303

# Sheldrick geometric approximatio 0.84 0.89 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_T_max  0.89
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
#_diffrn_ambient_temperature 150.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (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  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_measurement_method       'ω scans'


# If a reference occurs more than once, delete the author 
# and date from subsequent references. 

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'

_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            35545
_reflns_number_total             2996
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_av_sigmaI/netI    0.0312


# Number of reflections without Friedels Law is 2996 
# Number of reflections with Friedels Law is 1729 
# Theoretical number of reflections is about 1504 


_diffrn_reflns_theta_min         5.302
_diffrn_reflns_theta_max         73.748
_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        73.748
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              16

_oxford_diffrn_Wilson_B_factor   2.31
_oxford_diffrn_Wilson_scale      0.01

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.35
_refine_diff_density_max         0.40


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns         2996
_refine_ls_number_restraints     0
_refine_ls_number_parameters     191
_oxford_refine_ls_R_factor_ref   0.0341
_refine_ls_wR_factor_ref         0.0921
_refine_ls_goodness_of_fit_ref   1.0026
_refine_ls_shift/su_max          0.0004028
_refine_ls_shift/su_mean         0.0001095


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2996
_refine_ls_R_factor_all          0.0341
_refine_ls_wR_factor_all         0.0921

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2974
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_gt          0.0919

_refine_ls_abs_structure_Flack   -0.008(13)
_refine_ls_abs_structure_details 'Flack (1983), 1267 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.07P)² + 0.39P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_special_details          
# see also _refine_ls_hydrogen for refinement keywords.                         
;                                                                               

Hydrogen atoms were 
observed in a difference electron density map
and were included at calculated positions.
The H atoms were initially refined with soft restraints on the 
bond lengths and angles to regularise their geometry 
(C---H in the range 0.93--0.98Å\) and with
Uiso(H) in the range 1.2-1.5 times Ueq of the parent atom. 
and finally refined with riding constraints.



The largest peaks in the final difference electron density map 
were located near the Cl atom and between bonded atoms.
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Cl1 Cl 0.68552(4) 0.70676(4) 0.35122(4) 0.0357 1.0000 Uani . . . . . .
O1 O 0.42433(10) 0.68838(11) 0.23603(8) 0.0213 1.0000 Uani . . . . . .
O2 O 0.08506(12) 0.44018(11) 0.09750(8) 0.0277 1.0000 Uani . . . . . .
N1 N 0.11649(12) 0.55111(12) 0.24192(9) 0.0185 1.0000 Uani . . . . . .
C1 C 0.14978(15) 0.51118(13) 0.14900(11) 0.0205 1.0000 Uani . . . . . .
C2 C 0.27840(16) 0.56888(15) 0.12214(11) 0.0232 1.0000 Uani . . . . . .
C3 C 0.29579(15) 0.67337(15) 0.19913(11) 0.0194 1.0000 Uani . . . . . .
C4 C 0.21341(14) 0.63094(14) 0.28845(10) 0.0173 1.0000 Uani . . . . . .
C5 C 0.15940(14) 0.74035(14) 0.34899(12) 0.0215 1.0000 Uani . . . . . .
C6 C 0.26645(16) 0.83670(15) 0.36870(12) 0.0239 1.0000 Uani . . . . . .
C7 C 0.39226(15) 0.77581(15) 0.40330(11) 0.0229 1.0000 Uani . . . . . .
C8 C 0.42440(15) 0.65863(14) 0.34177(11) 0.0196 1.0000 Uani . . . . . .
C9 C 0.31532(14) 0.56323(14) 0.35164(11) 0.0190 1.0000 Uani . . . . . .
C10 C 0.55235(16) 0.60050(16) 0.36775(13) 0.0256 1.0000 Uani . . . . . .
C11 C -0.00636(15) 0.52077(15) 0.28720(11) 0.0207 1.0000 Uani . . . . . .
C12 C -0.00108(14) 0.42104(14) 0.36747(11) 0.0189 1.0000 Uani . . . . . .
C13 C -0.07932(16) 0.43315(16) 0.45108(12) 0.0248 1.0000 Uani . . . . . .
C14 C -0.08091(18) 0.34030(19) 0.52357(13) 0.0327 1.0000 Uani . . . . . .
C15 C -0.00765(19) 0.23372(17) 0.51228(13) 0.0324 1.0000 Uani . . . . . .
C16 C 0.07017(18) 0.22041(16) 0.42963(14) 0.0296 1.0000 Uani . . . . . .
C17 C 0.07472(16) 0.31402(15) 0.35771(12) 0.0235 1.0000 Uani . . . . . .
H21 H 0.2792 0.6005 0.0553 0.0282 1.0000 Uiso R . . . . .
H22 H 0.3467 0.5084 0.1302 0.0274 1.0000 Uiso R . . . . .
H31 H 0.2669 0.7551 0.1732 0.0227 1.0000 Uiso R . . . . .
H51 H 0.1257 0.7095 0.4135 0.0263 1.0000 Uiso R . . . . .
H52 H 0.0891 0.7801 0.3126 0.0277 1.0000 Uiso R . . . . .
H61 H 0.2371 0.8972 0.4182 0.0299 1.0000 Uiso R . . . . .
H62 H 0.2827 0.8804 0.3068 0.0283 1.0000 Uiso R . . . . .
H71 H 0.4615 0.8357 0.3949 0.0285 1.0000 Uiso R . . . . .
H72 H 0.3872 0.7493 0.4744 0.0270 1.0000 Uiso R . . . . .
H91 H 0.2902 0.5526 0.4211 0.0236 1.0000 Uiso R . . . . .
H92 H 0.3381 0.4813 0.3218 0.0236 1.0000 Uiso R . . . . .
H101 H 0.5515 0.5723 0.4373 0.0309 1.0000 Uiso R . . . . .
H102 H 0.5716 0.5294 0.3229 0.0290 1.0000 Uiso R . . . . .
H111 H -0.0413 0.5974 0.3171 0.0250 1.0000 Uiso R . . . . .
H112 H -0.0621 0.4911 0.2332 0.0248 1.0000 Uiso R . . . . .
H131 H -0.1326 0.5043 0.4572 0.0305 1.0000 Uiso R . . . . .
H141 H -0.1330 0.3521 0.5819 0.0397 1.0000 Uiso R . . . . .
H151 H -0.0092 0.1730 0.5587 0.0401 1.0000 Uiso R . . . . .
H161 H 0.1211 0.1502 0.4219 0.0363 1.0000 Uiso R . . . . .
H171 H 0.1291 0.3049 0.3021 0.0288 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          8.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 . C10 . 1.8026(17) yes
O1 . C3 . 1.4350(18) yes
O1 . C8 . 1.4540(17) yes
O2 . C1 . 1.2259(19) yes
N1 . C1 . 1.3622(19) yes
N1 . C4 . 1.4593(18) yes
N1 . C11 . 1.4516(19) yes
C1 . C2 . 1.516(2) yes
C2 . C3 . 1.529(2) yes
C2 . H21 . 0.959 no
C2 . H22 . 0.965 no
C3 . C4 . 1.541(2) yes
C3 . H31 . 0.984 no
C4 . C5 . 1.528(2) yes
C4 . C9 . 1.5373(19) yes
C5 . C6 . 1.537(2) yes
C5 . H51 . 0.990 no
C5 . H52 . 0.976 no
C6 . C7 . 1.533(2) yes
C6 . H61 . 0.974 no
C6 . H62 . 0.967 no
C7 . C8 . 1.533(2) yes
C7 . H71 . 0.969 no
C7 . H72 . 0.996 no
C8 . C9 . 1.529(2) yes
C8 . C10 . 1.509(2) yes
C9 . H91 . 0.975 no
C9 . H92 . 0.988 no
C10 . H101 . 0.981 no
C10 . H102 . 0.987 no
C11 . C12 . 1.514(2) yes
C11 . H111 . 0.980 no
C11 . H112 . 0.981 no
C12 . C13 . 1.392(2) yes
C12 . C17 . 1.392(2) yes
C13 . C14 . 1.387(2) yes
C13 . H131 . 0.943 no
C14 . C15 . 1.376(3) yes
C14 . H141 . 0.961 no
C15 . C16 . 1.381(3) yes
C15 . H151 . 0.898 no
C16 . C17 . 1.388(2) yes
C16 . H161 . 0.922 no
C17 . H171 . 0.942 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 . O1 . C8 . 108.24(11) yes
C1 . N1 . C4 . 113.45(12) yes
C1 . N1 . C11 . 122.52(13) yes
C4 . N1 . C11 . 123.98(12) yes
N1 . C1 . O2 . 124.68(15) yes
N1 . C1 . C2 . 108.39(13) yes
O2 . C1 . C2 . 126.93(14) yes
C1 . C2 . C3 . 103.81(12) yes
C1 . C2 . H21 . 111.9 no
C3 . C2 . H21 . 112.1 no
C1 . C2 . H22 . 110.6 no
C3 . C2 . H22 . 108.9 no
H21 . C2 . H22 . 109.4 no
C2 . C3 . O1 . 115.12(13) yes
C2 . C3 . C4 . 104.26(12) yes
O1 . C3 . C4 . 106.41(11) yes
C2 . C3 . H31 . 111.6 no
O1 . C3 . H31 . 107.9 no
C4 . C3 . H31 . 111.4 no
C3 . C4 . N1 . 102.84(11) yes
C3 . C4 . C5 . 113.23(12) yes
N1 . C4 . C5 . 114.70(12) yes
C3 . C4 . C9 . 100.55(11) yes
N1 . C4 . C9 . 116.06(12) yes
C5 . C4 . C9 . 108.55(12) yes
C4 . C5 . C6 . 109.52(12) yes
C4 . C5 . H51 . 110.0 no
C6 . C5 . H51 . 109.1 no
C4 . C5 . H52 . 109.9 no
C6 . C5 . H52 . 109.9 no
H51 . C5 . H52 . 108.4 no
C5 . C6 . C7 . 112.85(13) yes
C5 . C6 . H61 . 109.4 no
C7 . C6 . H61 . 110.0 no
C5 . C6 . H62 . 107.5 no
C7 . C6 . H62 . 108.3 no
H61 . C6 . H62 . 108.8 no
C6 . C7 . C8 . 111.56(12) yes
C6 . C7 . H71 . 108.7 no
C8 . C7 . H71 . 108.1 no
C6 . C7 . H72 . 111.4 no
C8 . C7 . H72 . 107.3 no
H71 . C7 . H72 . 109.7 no
C7 . C8 . O1 . 110.38(12) yes
C7 . C8 . C9 . 109.41(12) yes
O1 . C8 . C9 . 103.24(11) yes
C7 . C8 . C10 . 113.70(13) yes
O1 . C8 . C10 . 108.38(12) yes
C9 . C8 . C10 . 111.23(13) yes
C4 . C9 . C8 . 98.76(11) yes
C4 . C9 . H91 . 113.4 no
C8 . C9 . H91 . 111.0 no
C4 . C9 . H92 . 110.9 no
C8 . C9 . H92 . 111.9 no
H91 . C9 . H92 . 110.4 no
C8 . C10 . Cl1 . 113.08(11) yes
C8 . C10 . H101 . 109.8 no
Cl1 . C10 . H101 . 108.4 no
C8 . C10 . H102 . 110.7 no
Cl1 . C10 . H102 . 104.5 no
H101 . C10 . H102 . 110.3 no
N1 . C11 . C12 . 114.97(12) yes
N1 . C11 . H111 . 108.3 no
C12 . C11 . H111 . 107.8 no
N1 . C11 . H112 . 106.5 no
C12 . C11 . H112 . 108.7 no
H111 . C11 . H112 . 110.6 no
C11 . C12 . C13 . 119.17(14) yes
C11 . C12 . C17 . 121.88(13) yes
C13 . C12 . C17 . 118.87(14) yes
C12 . C13 . C14 . 120.40(16) yes
C12 . C13 . H131 . 119.3 no
C14 . C13 . H131 . 120.3 no
C13 . C14 . C15 . 120.29(16) yes
C13 . C14 . H141 . 119.0 no
C15 . C14 . H141 . 120.7 no
C14 . C15 . C16 . 119.88(15) yes
C14 . C15 . H151 . 120.5 no
C16 . C15 . H151 . 119.6 no
C15 . C16 . C17 . 120.31(16) yes
C15 . C16 . H161 . 120.7 no
C17 . C16 . H161 . 119.0 no
C12 . C17 . C16 . 120.21(15) yes
C12 . C17 . H171 . 120.0 no
C16 . C17 . H171 . 119.8 no


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 O1 C3 C2 -115.34(13) . . . . no
C8 O1 C3 C4 -0.40(15) . . . . no
C3 O1 C8 C7 -87.70(14) . . . . no
C3 O1 C8 C9 29.14(15) . . . . no
C3 O1 C8 C10 147.19(13) . . . . no
C4 N1 C1 O2 177.53(14) . . . . no
C4 N1 C1 C2 -2.25(17) . . . . no
C11 N1 C1 O2 -5.0(2) . . . . no
C11 N1 C1 C2 175.19(13) . . . . no
C1 N1 C4 C3 18.11(16) . . . . no
C1 N1 C4 C5 141.49(13) . . . . no
C1 N1 C4 C9 -90.58(15) . . . . no
C11 N1 C4 C3 -159.28(13) . . . . no
C11 N1 C4 C5 -35.90(19) . . . . no
C11 N1 C4 C9 92.03(16) . . . . no
C1 N1 C11 C12 104.87(16) . . . . no
C4 N1 C11 C12 -77.97(18) . . . . no
O2 C1 C2 C3 165.43(15) . . . . no
N1 C1 C2 C3 -14.81(16) . . . . no
C1 C2 C3 O1 141.11(13) . . . . no
C1 C2 C3 C4 24.94(15) . . . . no
O1 C3 C4 N1 -148.07(12) . . . . no
O1 C3 C4 C5 87.58(14) . . . . no
O1 C3 C4 C9 -28.02(14) . . . . no
C2 C3 C4 N1 -25.97(15) . . . . no
C2 C3 C4 C5 -150.32(12) . . . . no
C2 C3 C4 C9 94.08(13) . . . . no
N1 C4 C5 C6 -164.09(12) . . . . no
C3 C4 C5 C6 -46.46(16) . . . . no
C9 C4 C5 C6 64.28(15) . . . . no
N1 C4 C9 C8 153.71(12) . . . . no
C3 C4 C9 C8 43.67(13) . . . . no
C5 C4 C9 C8 -75.39(13) . . . . no
C4 C5 C6 C7 -45.80(17) . . . . no
C5 C6 C7 C8 43.60(17) . . . . no
C6 C7 C8 O1 53.70(16) . . . . no
C6 C7 C8 C9 -59.25(16) . . . . no
C6 C7 C8 C10 175.73(13) . . . . no
O1 C8 C9 C4 -45.37(13) . . . . no
C7 C8 C9 C4 72.15(14) . . . . no
C10 C8 C9 C4 -161.41(12) . . . . no
O1 C8 C10 Cl1 64.19(15) . . . . no
C7 C8 C10 Cl1 -58.94(16) . . . . no
C9 C8 C10 Cl1 177.01(11) . . . . no
N1 C11 C12 C13 142.24(14) . . . . no
N1 C11 C12 C17 -41.3(2) . . . . no
C11 C12 C13 C14 176.98(15) . . . . no
C17 C12 C13 C14 0.4(2) . . . . no
C11 C12 C17 C16 -175.44(15) . . . . no
C13 C12 C17 C16 1.1(2) . . . . no
C12 C13 C14 C15 -1.7(3) . . . . no
C13 C14 C15 C16 1.6(3) . . . . no
C14 C15 C16 C17 -0.1(3) . . . . no
C15 C16 C17 C12 -1.2(3) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cl1 O1 3.1324(11) . . no
O1 C14 3.298(2) . 4_564 no
O1 C15 3.234(2) . 4_564 no
O2 C5 3.3932(19) . 3_545 no
O2 C16 3.413(2) . 3_555 no
C1 C17 3.587(2) . . no
C1 C16 3.364(2) . 3_555 no
C1 C15 3.534(2) . 3_555 no
C2 C15 3.505(2) . 4_564 no
C2 C14 3.548(2) . 4_564 no
C3 C15 3.482(2) . 4_564 no



_iucr_refine_instruction_details_constraints 
;
#
# Punched on 05/09/18 at 12:01:30
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   2,X'S) H   (  21,X'S) H   (  22,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) H   (  52,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) H   (  62,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  92,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 05/09/18 at 12:01:30
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;


#===END

####################################################################### 
# 
# 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_pyn1815SNQ
_database_code_depnum_ccdc_archive 'CCDC 2010551'
loop_
_audit_author_name
_audit_author_address
'Anthony Willis'
;Australian National University
Australia
;
_audit_update_record             
;
2020-06-18 deposited with the CCDC.	2020-11-11 downloaded from the CCDC.
;
_audit_creation_date             18-08-06
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'Z:\pyn1815SNQ\Tony_pyn1815SNQ_da At 13:22 on'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   12.2886(2)
_cell_length_b                   7.0684(1)
_cell_length_c                   13.9005(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.4956(13)
_cell_angle_gamma                90
_cell_volume                     1168.97(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1 '
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Si 0.2541 0.3302 6.2915 2.4386 3.0353 32.3337 1.9891 0.6785 1.5410 81.6937
1.1407 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C23 H34 Cl1 N1 O2 Si1 
# Dc =      1.19 Fooo =    452.00 Mu =     20.67 M =    420.07
# Found Formula = C23 H34 Cl1 N1 O2 Si1 
# Dc =      1.19 FOOO =    452.00 Mu =     20.67 M =    420.07

_chemical_formula_sum            'C23 H34 Cl N O2 Si'
_chemical_formula_moiety         'C23 H34 Cl N O2 Si'
_chemical_compound_source        ' from U of Wollongong '
_chemical_formula_weight         420.07


_cell_measurement_reflns_used    20023
_cell_measurement_theta_min      4
_cell_measurement_theta_max      74
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.079
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_max          0.300

_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             452
_exptl_absorpt_coefficient_mu    2.067

# Sheldrick geometric approximatio 0.68 0.85 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_T_max  0.85
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
#_diffrn_ambient_temperature 150.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (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  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_measurement_method       'ω scans'


# If a reference occurs more than once, delete the author 
# and date from subsequent references. 

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'

_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            23411
_reflns_number_total             3904
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_av_sigmaI/netI    0.0232


# Number of reflections without Friedels Law is 3904 
# Number of reflections with Friedels Law is 2572 
# Theoretical number of reflections is about 2370 


_diffrn_reflns_theta_min         3.715
_diffrn_reflns_theta_max         73.910
_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        73.910
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -15
_reflns_limit_h_max              14
_reflns_limit_k_min              -8
_reflns_limit_k_max              5
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_oxford_diffrn_Wilson_B_factor   3.19
_oxford_diffrn_Wilson_scale      0.02

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.29
_refine_diff_density_max         0.28


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns         3904
_refine_ls_number_restraints     1
_refine_ls_number_parameters     254
_oxford_refine_ls_R_factor_ref   0.0480
_refine_ls_wR_factor_ref         0.1340
_refine_ls_goodness_of_fit_ref   1.0042
_refine_ls_shift/su_max          0.0003849
_refine_ls_shift/su_mean         0.0000456


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3904
_refine_ls_R_factor_all          0.0480
_refine_ls_wR_factor_all         0.1340

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3883
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_gt          0.1339

_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_abs_structure_details 'Flack (1983), 1332 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.09P)² + 0.55P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_special_details          
# see also _refine_ls_hydrogen for refinement keywords.                         
;                                                                               
The displacement ellipsoids of C18, C19, C21 and C22 are all
elongated tangentially with regard to the O2---Si1 vector.
This suggests that there is significant disorder in the packing of
the TBSO group.  Examination of a slant Fourier electron-density map 
shows that the electron-densities of these atoms are not 'peanut shaped', 
which would suggest 2 main locations for each atom, 
but, rather, there is an arc of electron-density
more consistent with there being a superposition of many possible sites, 
and that the highest probability is at the centre.

Hydrogen atoms, with the exception of those of the TBSO group, were 
observed in a difference electron density map.
H atoms were all included at calculated positions.
The H atoms were initially refined with soft restraints on the 
bond lengths and angles to regularise their geometry 
(C---H in the range 0.93--0.98Å\) and with
Uiso(H) in the range 1.2-1.5 times Ueq of the parent atom. 
and finally refined with riding constraints.



The largest peaks in the final difference electron density map 
were located near the Cl  and Si atoms.
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Cl1 Cl 0.38025(7) 0.2993(2) -0.06923(5) 0.0604 1.0000 Uani . . . . . .
Si1 Si 0.75647(6) 0.2364(2) 0.38795(6) 0.0449 1.0000 Uani . . . . . .
O1 O 0.46681(18) 0.8066(3) 0.34940(15) 0.0457 1.0000 Uani . . . . . .
O2 O 0.63579(13) 0.3301(3) 0.32765(11) 0.0315 1.0000 Uani . . . . . .
N1 N 0.41710(16) 0.5341(3) 0.25913(14) 0.0259 1.0000 Uani . . . . . .
C1 C 0.4678(2) 0.6345(4) 0.34155(19) 0.0319 1.0000 Uani . . . . . .
C2 C 0.5250(2) 0.4958(5) 0.42054(18) 0.0376 1.0000 Uani . . . . . .
C3 C 0.53652(19) 0.3182(4) 0.36251(16) 0.0303 1.0000 Uani . . . . . .
C4 C 0.43178(19) 0.3273(4) 0.27308(16) 0.0265 1.0000 Uani . . . . . .
C5 C 0.45077(18) 0.2254(4) 0.18171(17) 0.0291 1.0000 Uani . . . . . .
C6 C 0.3437(2) 0.1721(4) 0.10679(19) 0.0334 1.0000 Uani . . . . . .
C7 C 0.2432(2) 0.1758(4) 0.1259(2) 0.0370 1.0000 Uani . . . . . .
C8 C 0.2236(2) 0.2340(5) 0.2228(2) 0.0383 1.0000 Uani . . . . . .
C9 C 0.3325(2) 0.2352(4) 0.30485(19) 0.0338 1.0000 Uani . . . . . .
C10 C 0.3682(2) 0.6329(4) 0.16596(17) 0.0280 1.0000 Uani . . . . . .
C11 C 0.2441(2) 0.6780(4) 0.14616(17) 0.0276 1.0000 Uani . . . . . .
C12 C 0.1953(2) 0.7357(4) 0.22085(18) 0.0321 1.0000 Uani . . . . . .
C13 C 0.0825(2) 0.7798(4) 0.2005(2) 0.0374 1.0000 Uani . . . . . .
C14 C 0.0165(2) 0.7698(5) 0.1041(2) 0.0431 1.0000 Uani . . . . . .
C15 C 0.0642(2) 0.7140(6) 0.0288(2) 0.0469 1.0000 Uani . . . . . .
C16 C 0.1771(2) 0.6663(5) 0.04908(19) 0.0360 1.0000 Uani . . . . . .
C17 C 0.3545(3) 0.1040(5) 0.0082(2) 0.0468 1.0000 Uani . . . . . .
C18 C 0.7421(5) -0.0232(10) 0.3935(10) 0.2239 1.0000 Uani . . . . . .
C19 C 0.7977(3) 0.3237(15) 0.5147(2) 0.1544 1.0000 Uani . . . . . .
C20 C 0.8586(2) 0.3041(8) 0.3170(2) 0.0619 1.0000 Uani . . . . . .
C21 C 0.8274(5) 0.2227(17) 0.2142(3) 0.1732 1.0000 Uani . . . . . .
C22 C 0.8557(5) 0.5223(12) 0.3074(7) 0.1452 1.0000 Uani . . . . . .
C23 C 0.9776(3) 0.2386(11) 0.3705(3) 0.0989 1.0000 Uani . . . . . .
H21 H 0.5974 0.5436 0.4573 0.0452 1.0000 Uiso R . . . . .
H22 H 0.4817 0.4695 0.4673 0.0455 1.0000 Uiso R . . . . .
H31 H 0.5344 0.2036 0.3975 0.0345 1.0000 Uiso R . . . . .
H51 H 0.4942 0.3073 0.1492 0.0343 1.0000 Uiso R . . . . .
H52 H 0.4945 0.1109 0.2040 0.0349 1.0000 Uiso R . . . . .
H71 H 0.1818 0.1392 0.0752 0.0435 1.0000 Uiso R . . . . .
H81 H 0.1907 0.3598 0.2161 0.0449 1.0000 Uiso R . . . . .
H82 H 0.1684 0.1458 0.2402 0.0456 1.0000 Uiso R . . . . .
H91 H 0.3240 0.3023 0.3649 0.0406 1.0000 Uiso R . . . . .
H92 H 0.3539 0.1057 0.3224 0.0396 1.0000 Uiso R . . . . .
H101 H 0.4087 0.7516 0.1685 0.0332 1.0000 Uiso R . . . . .
H102 H 0.3822 0.5542 0.1141 0.0335 1.0000 Uiso R . . . . .
H121 H 0.2397 0.7435 0.2848 0.0387 1.0000 Uiso R . . . . .
H131 H 0.0512 0.8184 0.2519 0.0455 1.0000 Uiso R . . . . .
H141 H -0.0608 0.8007 0.0910 0.0516 1.0000 Uiso R . . . . .
H151 H 0.0190 0.7086 -0.0375 0.0559 1.0000 Uiso R . . . . .
H161 H 0.2085 0.6242 -0.0019 0.0422 1.0000 Uiso R . . . . .
H171 H 0.4193 0.0185 0.0185 0.0554 1.0000 Uiso R . . . . .
H172 H 0.2847 0.0383 -0.0259 0.0554 1.0000 Uiso R . . . . .
H181 H 0.7926 -0.0814 0.3600 0.3358 1.0000 Uiso R . . . . .
H182 H 0.7613 -0.0627 0.4616 0.3359 1.0000 Uiso R . . . . .
H183 H 0.6672 -0.0607 0.3622 0.3360 1.0000 Uiso R . . . . .
H191 H 0.8616 0.2551 0.5488 0.2309 1.0000 Uiso R . . . . .
H192 H 0.8156 0.4546 0.5124 0.2306 1.0000 Uiso R . . . . .
H193 H 0.7380 0.3062 0.5461 0.2309 1.0000 Uiso R . . . . .
H211 H 0.8782 0.2678 0.1774 0.2598 1.0000 Uiso R . . . . .
H212 H 0.8316 0.0865 0.2172 0.2598 1.0000 Uiso R . . . . .
H213 H 0.7520 0.2592 0.1804 0.2595 1.0000 Uiso R . . . . .
H221 H 0.8904 0.5582 0.2551 0.2169 1.0000 Uiso R . . . . .
H222 H 0.8965 0.5750 0.3683 0.2171 1.0000 Uiso R . . . . .
H223 H 0.7808 0.5673 0.2927 0.2170 1.0000 Uiso R . . . . .
H231 H 1.0257 0.2738 0.3285 0.1470 1.0000 Uiso R . . . . .
H232 H 1.0027 0.2979 0.4360 0.1473 1.0000 Uiso R . . . . .
H233 H 0.9790 0.1030 0.3778 0.1481 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          7.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 . C17 . 1.826(4) yes
Si1 . O2 . 1.6487(18) yes
Si1 . C18 . 1.847(7) yes
Si1 . C19 . 1.815(5) yes
Si1 . C20 . 1.843(3) yes
O1 . C1 . 1.221(3) yes
O2 . C3 . 1.423(3) yes
N1 . C1 . 1.359(3) yes
N1 . C4 . 1.480(3) yes
N1 . C10 . 1.462(3) yes
C1 . C2 . 1.508(4) yes
C2 . C3 . 1.518(4) yes
C2 . H21 . 0.969 no
C2 . H22 . 0.957 no
C3 . C4 . 1.551(3) yes
C3 . H31 . 0.949 no
C4 . C5 . 1.528(3) yes
C4 . C9 . 1.541(3) yes
C5 . C6 . 1.507(3) yes
C5 . H51 . 0.971 no
C5 . H52 . 0.978 no
C6 . C7 . 1.327(4) yes
C6 . C17 . 1.489(4) yes
C7 . C8 . 1.485(4) yes
C7 . H71 . 0.931 no
C8 . C9 . 1.526(4) yes
C8 . H81 . 0.971 no
C8 . H82 . 0.994 no
C9 . H91 . 0.989 no
C9 . H92 . 0.966 no
C10 . C11 . 1.514(3) yes
C10 . H101 . 0.971 no
C10 . H102 . 0.960 no
C11 . C12 . 1.384(3) yes
C11 . C16 . 1.396(3) yes
C12 . C13 . 1.379(4) yes
C12 . H121 . 0.921 no
C13 . C14 . 1.383(4) yes
C13 . H131 . 0.933 no
C14 . C15 . 1.379(4) yes
C14 . H141 . 0.947 no
C15 . C16 . 1.387(4) yes
C15 . H151 . 0.950 no
C16 . H161 . 0.936 no
C17 . H171 . 0.981 no
C17 . H172 . 0.986 no
C18 . H181 . 0.957 no
C18 . H182 . 0.958 no
C18 . H183 . 0.952 no
C19 . H191 . 0.944 no
C19 . H192 . 0.954 no
C19 . H193 . 0.951 no
C20 . C21 . 1.498(6) yes
C20 . C22 . 1.548(9) yes
C20 . C23 . 1.538(5) yes
C21 . H211 . 0.956 no
C21 . H212 . 0.965 no
C21 . H213 . 0.964 no
C22 . H221 . 0.964 no
C22 . H222 . 0.946 no
C22 . H223 . 0.947 no
C23 . H231 . 0.961 no
C23 . H232 . 0.979 no
C23 . H233 . 0.964 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 . Si1 . C18 . 109.7(2) yes
O2 . Si1 . C19 . 110.7(2) yes
C18 . Si1 . C19 . 107.7(5) yes
O2 . Si1 . C20 . 105.65(13) yes
C18 . Si1 . C20 . 111.4(4) yes
C19 . Si1 . C20 . 111.7(2) yes
Si1 . O2 . C3 . 122.80(15) yes
C1 . N1 . C4 . 113.0(2) yes
C1 . N1 . C10 . 119.8(2) yes
C4 . N1 . C10 . 126.71(19) yes
N1 . C1 . O1 . 125.6(3) yes
N1 . C1 . C2 . 107.8(2) yes
O1 . C1 . C2 . 126.5(2) yes
C1 . C2 . C3 . 103.8(2) yes
C1 . C2 . H21 . 110.9 no
C3 . C2 . H21 . 111.9 no
C1 . C2 . H22 . 112.6 no
C3 . C2 . H22 . 110.0 no
H21 . C2 . H22 . 107.7 no
C2 . C3 . O2 . 109.5(2) yes
C2 . C3 . C4 . 102.9(2) yes
O2 . C3 . C4 . 109.56(17) yes
C2 . C3 . H31 . 114.5 no
O2 . C3 . H31 . 111.1 no
C4 . C3 . H31 . 108.9 no
C3 . C4 . N1 . 101.3(2) yes
C3 . C4 . C5 . 112.21(19) yes
N1 . C4 . C5 . 113.31(19) yes
C3 . C4 . C9 . 108.07(19) yes
N1 . C4 . C9 . 112.1(2) yes
C5 . C4 . C9 . 109.6(2) yes
C4 . C5 . C6 . 113.82(19) yes
C4 . C5 . H51 . 108.7 no
C6 . C5 . H51 . 108.3 no
C4 . C5 . H52 . 108.3 no
C6 . C5 . H52 . 109.1 no
H51 . C5 . H52 . 108.5 no
C5 . C6 . C7 . 123.5(2) yes
C5 . C6 . C17 . 117.0(2) yes
C7 . C6 . C17 . 119.5(2) yes
C6 . C7 . C8 . 123.9(2) yes
C6 . C7 . H71 . 117.6 no
C8 . C7 . H71 . 118.5 no
C7 . C8 . C9 . 111.6(2) yes
C7 . C8 . H81 . 108.9 no
C9 . C8 . H81 . 109.4 no
C7 . C8 . H82 . 108.8 no
C9 . C8 . H82 . 110.2 no
H81 . C8 . H82 . 107.7 no
C4 . C9 . C8 . 113.4(2) yes
C4 . C9 . H91 . 107.4 no
C8 . C9 . H91 . 112.0 no
C4 . C9 . H92 . 106.7 no
C8 . C9 . H92 . 108.4 no
H91 . C9 . H92 . 108.7 no
N1 . C10 . C11 . 115.69(19) yes
N1 . C10 . H101 . 106.7 no
C11 . C10 . H101 . 107.9 no
N1 . C10 . H102 . 106.1 no
C11 . C10 . H102 . 110.3 no
H101 . C10 . H102 . 110.0 no
C10 . C11 . C12 . 122.1(2) yes
C10 . C11 . C16 . 119.1(2) yes
C12 . C11 . C16 . 118.7(2) yes
C11 . C12 . C13 . 121.0(2) yes
C11 . C12 . H121 . 118.5 no
C13 . C12 . H121 . 120.5 no
C12 . C13 . C14 . 120.2(2) yes
C12 . C13 . H131 . 119.6 no
C14 . C13 . H131 . 120.2 no
C13 . C14 . C15 . 119.5(2) yes
C13 . C14 . H141 . 119.4 no
C15 . C14 . H141 . 121.1 no
C14 . C15 . C16 . 120.6(2) yes
C14 . C15 . H151 . 119.4 no
C16 . C15 . H151 . 120.0 no
C11 . C16 . C15 . 120.0(2) yes
C11 . C16 . H161 . 119.7 no
C15 . C16 . H161 . 120.3 no
Cl1 . C17 . C6 . 111.5(2) yes
Cl1 . C17 . H171 . 107.3 no
C6 . C17 . H171 . 108.8 no
Cl1 . C17 . H172 . 109.3 no
C6 . C17 . H172 . 109.1 no
H171 . C17 . H172 . 110.9 no
Si1 . C18 . H181 . 109.1 no
Si1 . C18 . H182 . 109.1 no
H181 . C18 . H182 . 109.0 no
Si1 . C18 . H183 . 110.4 no
H181 . C18 . H183 . 109.2 no
H182 . C18 . H183 . 109.9 no
Si1 . C19 . H191 . 108.0 no
Si1 . C19 . H192 . 108.0 no
H191 . C19 . H192 . 110.2 no
Si1 . C19 . H193 . 110.0 no
H191 . C19 . H193 . 110.1 no
H192 . C19 . H193 . 110.6 no
Si1 . C20 . C21 . 111.4(4) yes
Si1 . C20 . C22 . 107.5(3) yes
C21 . C20 . C22 . 107.8(6) yes
Si1 . C20 . C23 . 110.8(3) yes
C21 . C20 . C23 . 109.3(4) yes
C22 . C20 . C23 . 109.9(4) yes
C20 . C21 . H211 . 109.7 no
C20 . C21 . H212 . 110.1 no
H211 . C21 . H212 . 108.7 no
C20 . C21 . H213 . 110.4 no
H211 . C21 . H213 . 109.0 no
H212 . C21 . H213 . 108.9 no
C20 . C22 . H221 . 108.8 no
C20 . C22 . H222 . 108.7 no
H221 . C22 . H222 . 109.7 no
C20 . C22 . H223 . 110.7 no
H221 . C22 . H223 . 109.8 no
H222 . C22 . H223 . 109.3 no
C20 . C23 . H231 . 106.4 no
C20 . C23 . H232 . 111.1 no
H231 . C23 . H232 . 110.9 no
C20 . C23 . H233 . 109.8 no
H231 . C23 . H233 . 108.9 no
H232 . C23 . H233 . 109.6 no


loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C18 Si1 O2 C3 63.4(4) . . . . no
C19 Si1 O2 C3 -55.3(4) . . . . no
C20 Si1 O2 C3 -176.4(2) . . . . no
O2 Si1 C20 C21 -62.7(5) . . . . no
O2 Si1 C20 C22 55.2(4) . . . . no
O2 Si1 C20 C23 175.4(4) . . . . no
C18 Si1 C20 C21 56.4(6) . . . . no
C18 Si1 C20 C22 174.3(5) . . . . no
C18 Si1 C20 C23 -65.5(6) . . . . no
C19 Si1 C20 C21 176.9(6) . . . . no
C19 Si1 C20 C22 -65.2(5) . . . . no
C19 Si1 C20 C23 54.9(5) . . . . no
Si1 O2 C3 C2 95.3(2) . . . . no
Si1 O2 C3 C4 -152.61(19) . . . . no
C4 N1 C1 O1 -179.1(2) . . . . no
C4 N1 C1 C2 1.0(3) . . . . no
C10 N1 C1 O1 8.4(4) . . . . no
C10 N1 C1 C2 -171.5(2) . . . . no
C1 N1 C4 C3 -20.9(2) . . . . no
C1 N1 C4 C5 -141.2(2) . . . . no
C1 N1 C4 C9 94.1(2) . . . . no
C10 N1 C4 C3 151.0(2) . . . . no
C10 N1 C4 C5 30.7(3) . . . . no
C10 N1 C4 C9 -94.0(3) . . . . no
C1 N1 C10 C11 -94.1(3) . . . . no
C4 N1 C10 C11 94.5(3) . . . . no
O1 C1 C2 C3 -160.0(3) . . . . no
N1 C1 C2 C3 19.9(3) . . . . no
C1 C2 C3 O2 84.8(2) . . . . no
C1 C2 C3 C4 -31.7(2) . . . . no
O2 C3 C4 N1 -84.9(2) . . . . no
O2 C3 C4 C5 36.2(3) . . . . no
O2 C3 C4 C9 157.2(2) . . . . no
C2 C3 C4 N1 31.5(2) . . . . no
C2 C3 C4 C5 152.6(2) . . . . no
C2 C3 C4 C9 -86.4(2) . . . . no
N1 C4 C5 C6 -85.9(3) . . . . no
C3 C4 C5 C6 160.2(2) . . . . no
C9 C4 C5 C6 40.1(3) . . . . no
N1 C4 C9 C8 69.6(3) . . . . no
C3 C4 C9 C8 -179.7(2) . . . . no
C5 C4 C9 C8 -57.1(3) . . . . no
C4 C5 C6 C7 -13.5(4) . . . . no
C4 C5 C6 C17 169.4(2) . . . . no
C5 C6 C7 C8 0.5(5) . . . . no
C17 C6 C7 C8 177.6(3) . . . . no
C5 C6 C17 Cl1 -76.2(3) . . . . no
C7 C6 C17 Cl1 106.5(3) . . . . no
C6 C7 C8 C9 -15.9(4) . . . . no
C7 C8 C9 C4 44.5(3) . . . . no
N1 C10 C11 C12 38.8(4) . . . . no
N1 C10 C11 C16 -143.1(3) . . . . no
C10 C11 C12 C13 178.6(3) . . . . no
C16 C11 C12 C13 0.5(4) . . . . no
C10 C11 C16 C15 -177.5(3) . . . . no
C12 C11 C16 C15 0.7(5) . . . . no
C11 C12 C13 C14 -1.1(4) . . . . no
C12 C13 C14 C15 0.5(5) . . . . no
C13 C14 C15 C16 0.6(6) . . . . no
C14 C15 C16 C11 -1.2(6) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 C12 3.405(3) . . no
O2 N1 2.988(3) . . no
C1 C12 3.425(4) . . no
C2 C19 3.497(6) . . no
C6 C10 3.354(4) . . no
C7 C11 3.530(4) . 1_545 no
C7 C10 3.561(4) . . no
C7 C11 3.561(4) . . no
C7 C12 3.486(4) . 1_545 no
C8 C12 3.539(5) . 1_545 no
C8 C11 3.344(4) . . no
C8 C10 3.526(4) . . no
C8 C12 3.563(5) . . no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 06/08/18 at 14:03:33
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   2,X'S) H   (  21,X'S) H   (  22,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) H   (  52,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  92,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) H   ( 183,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) H   ( 193,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 212,X'S) H   ( 213,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) H   ( 223,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 232,X'S) H   ( 233,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 06/08/18 at 14:03:33
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
# start Validation Reply Form 
_vrf_PLAT213_pyn1815SNQ          
; 
PROBLEM: Atom C18             has ADP max/min Ratio .....        4.7 prolat 
RESPONSE: ... see refine special details.  There is a degree of disorder
of the packing of the TBSO group around the Si---O bond.
;
_vrf_PLAT220_pyn1815SNQ          
; 
PROBLEM: Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range        8.5 Ratio  
RESPONSE: ... see refine special details.  There is a degree of disorder
of the packing of the TBSO group around the Si---O bond.
;
_vrf_PLAT242_pyn1815SNQ          
; 
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of        Si1 Check  
RESPONSE: ... see refine special details.  There is a degree of disorder
of the packing of the TBSO group around the Si---O bond.  The Si is at the 
centre, so has a lower Ueq than its neighbours. 
;
# end Validation Reply Form

#===END

####################################################################### 
# 
# 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_pyn1901SNQM
_database_code_depnum_ccdc_archive 'CCDC 2010555'
loop_
_audit_author_name
_audit_author_address
'Anthony Willis'
;Australian National University
Australia
;
_audit_update_record             
;
2020-06-18 deposited with the CCDC.	2020-11-11 downloaded from the CCDC.
;
_audit_creation_date             19-01-18
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'Z:\pyn1901SNQM\Tony_pyn1901SNQM_ At 11:45 on'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   10.6602(5)
_cell_length_b                   8.6837(3)
_cell_length_c                   12.1854(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.849(3)
_cell_angle_gamma                90
_cell_volume                     1126.61(8)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1 '
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C28 H26 N2 O2 
# Dc =      1.25 Fooo =    448.00 Mu =      0.79 M =    422.53
# Found Formula = C28 H26 N2 O2 
# Dc =      1.25 FOOO =    448.00 Mu =      0.79 M =    422.53

_chemical_formula_sum            'C28 H26 N2 O2'
_chemical_formula_moiety         'C28 H26 N2 O2'
_chemical_compound_source        ' from U of Wollongong '
_chemical_formula_weight         422.53


_cell_measurement_reflns_used    6066
_cell_measurement_theta_min      4
_cell_measurement_theta_max      26
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.067
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_max          0.287

_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.079

# Sheldrick geometric approximatio 0.99 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.99
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
#_diffrn_ambient_temperature 150.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_source         
'SuperMova (Mo) X-ray Source' ################
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_measurement_method       'ω scans'


# If a reference occurs more than once, delete the author 
# and date from subsequent references. 

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'

_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            18376
_reflns_number_total             2456
_diffrn_reflns_av_R_equivalents  0.047
_diffrn_reflns_av_sigmaI/netI    0.0621

# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2456 
# Theoretical number of reflections is about 4604 


_diffrn_reflns_theta_min         3.413
_diffrn_reflns_theta_max         26.364
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        26.364
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -13
_reflns_limit_h_max              13
_reflns_limit_k_min              0
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              15

_oxford_diffrn_Wilson_B_factor   2.52
_oxford_diffrn_Wilson_scale      0.03

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.25
_refine_diff_density_max         0.23


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns         2456
_refine_ls_number_restraints     1
_refine_ls_number_parameters     292
_oxford_refine_ls_R_factor_ref   0.0461
_refine_ls_wR_factor_ref         0.0960
_refine_ls_goodness_of_fit_ref   1.0171
_refine_ls_shift/su_max          0.0006592
_refine_ls_shift/su_mean         0.0000640


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2456
_refine_ls_R_factor_all          0.0461
_refine_ls_wR_factor_all         0.0960

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2268
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_gt          0.0935

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration syn
_refine_ls_abs_structure_details 
;
The enantiomer has been assigned by reference to an unchanging chiral
centre in the synthetic procedure.
;


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.03P)² + 0.53P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_special_details          
# see also _refine_ls_hydrogen for refinement keywords.                         
;                                                                               

Hydrogen atoms were 
observed in a difference electron density map
and those bonded to C were included at calculated positions.
The H atoms were initially refined with soft restraints on the 
bond lengths and angles to regularise their geometry 
(C---H in the range 0.93--0.98Å, N---H = 0.87Å) and with
Uiso(H) in the range 1.2-1.5 times Ueq of the parent atom. 
Finally the H atom bonded to N was refined without restraints
and H atoms bonded to C were refined with riding constraints.



The largest peaks in the final difference electron density map 
were located between bonded atoms.
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.5146(2) 0.6183(3) 0.40833(17) 0.0485 1.0000 Uani . . . . . .
O2 O 0.36632(18) 0.5911(2) 0.76838(16) 0.0352 1.0000 Uani . . . . . .
N1 N 0.60793(19) 0.5528(3) 0.57466(17) 0.0270 1.0000 Uani . . . . . .
N2 N 0.6583(2) 0.2665(3) 0.73504(19) 0.0249 1.0000 Uani . . . . . .
C1 C 0.5108(3) 0.5998(4) 0.5084(3) 0.0337 1.0000 Uani . . . . . .
C2 C 0.3991(3) 0.6236(4) 0.5772(2) 0.0355 1.0000 Uani . . . . . .
C3 C 0.4334(2) 0.5315(3) 0.6808(2) 0.0273 1.0000 Uani . . . . . .
C4 C 0.5799(2) 0.5476(3) 0.6922(2) 0.0247 1.0000 Uani . . . . . .
C5 C 0.7315(3) 0.5169(3) 0.5345(2) 0.0310 1.0000 Uani . . . . . .
C6 C 0.8318(3) 0.6316(4) 0.5679(2) 0.0342 1.0000 Uani . . . . . .
C7 C 0.9325(3) 0.5904(5) 0.6383(3) 0.0454 1.0000 Uani . . . . . .
C8 C 1.0249(3) 0.6999(6) 0.6666(3) 0.0626 1.0000 Uani . . . . . .
C9 C 1.0164(4) 0.8462(6) 0.6275(4) 0.0692 1.0000 Uani . . . . . .
C10 C 0.9165(4) 0.8881(5) 0.5593(4) 0.0721 1.0000 Uani . . . . . .
C11 C 0.8258(3) 0.7817(5) 0.5286(3) 0.0565 1.0000 Uani . . . . . .
C12 C 0.3805(3) 0.5069(4) 0.8705(2) 0.0360 1.0000 Uani . . . . . .
C13 C 0.3408(3) 0.3406(4) 0.8593(2) 0.0373 1.0000 Uani . . . . . .
C14 C 0.2191(3) 0.3031(5) 0.8241(3) 0.0487 1.0000 Uani . . . . . .
C15 C 0.1844(4) 0.1493(5) 0.8109(3) 0.0633 1.0000 Uani . . . . . .
C16 C 0.2720(5) 0.0349(5) 0.8324(3) 0.0654 1.0000 Uani . . . . . .
C17 C 0.3916(4) 0.0699(5) 0.8703(3) 0.0582 1.0000 Uani . . . . . .
C18 C 0.4252(4) 0.2228(4) 0.8842(3) 0.0458 1.0000 Uani . . . . . .
C19 C 0.6257(3) 0.6913(3) 0.7596(2) 0.0286 1.0000 Uani . . . . . .
C20 C 0.7283(3) 0.6413(3) 0.8489(2) 0.0278 1.0000 Uani . . . . . .
C21 C 0.7282(3) 0.4697(3) 0.8361(2) 0.0228 1.0000 Uani . . . . . .
C22 C 0.6506(2) 0.4220(3) 0.7519(2) 0.0227 1.0000 Uani . . . . . .
C23 C 0.7883(2) 0.3346(3) 0.8814(2) 0.0228 1.0000 Uani . . . . . .
C24 C 0.8740(2) 0.3028(3) 0.9697(2) 0.0268 1.0000 Uani . . . . . .
C25 C 0.9092(2) 0.1531(3) 0.9911(2) 0.0302 1.0000 Uani . . . . . .
C26 C 0.8612(2) 0.0319(3) 0.9258(2) 0.0303 1.0000 Uani . . . . . .
C27 C 0.7776(2) 0.0586(3) 0.8374(2) 0.0282 1.0000 Uani . . . . . .
C28 C 0.7414(2) 0.2098(3) 0.8162(2) 0.0237 1.0000 Uani . . . . . .
H1 H 0.609(3) 0.215(4) 0.693(2) 0.0303 1.0000 Uiso . . . . . .
H21 H 0.3891 0.7317 0.5981 0.0428 1.0000 Uiso R . . . . .
H22 H 0.3240 0.5873 0.5395 0.0426 1.0000 Uiso R . . . . .
H31 H 0.4133 0.4221 0.6673 0.0318 1.0000 Uiso R . . . . .
H51 H 0.7553 0.4154 0.5609 0.0370 1.0000 Uiso R . . . . .
H52 H 0.7222 0.5129 0.4552 0.0374 1.0000 Uiso R . . . . .
H71 H 0.9365 0.4909 0.6669 0.0537 1.0000 Uiso R . . . . .
H81 H 1.0926 0.6722 0.7138 0.0751 1.0000 Uiso R . . . . .
H91 H 1.0783 0.9183 0.6474 0.0828 1.0000 Uiso R . . . . .
H101 H 0.9105 0.9880 0.5337 0.0862 1.0000 Uiso R . . . . .
H111 H 0.7578 0.8101 0.4803 0.0686 1.0000 Uiso R . . . . .
H121 H 0.3272 0.5559 0.9221 0.0422 1.0000 Uiso R . . . . .
H122 H 0.4683 0.5128 0.8983 0.0432 1.0000 Uiso R . . . . .
H141 H 0.1592 0.3805 0.8070 0.0576 1.0000 Uiso R . . . . .
H151 H 0.1027 0.1234 0.7863 0.0757 1.0000 Uiso R . . . . .
H161 H 0.2485 -0.0676 0.8212 0.0783 1.0000 Uiso R . . . . .
H171 H 0.4492 -0.0110 0.8857 0.0706 1.0000 Uiso R . . . . .
H181 H 0.5096 0.2474 0.9114 0.0544 1.0000 Uiso R . . . . .
H191 H 0.5560 0.7377 0.7927 0.0336 1.0000 Uiso R . . . . .
H192 H 0.6596 0.7643 0.7096 0.0345 1.0000 Uiso R . . . . .
H201 H 0.7087 0.6743 0.9222 0.0337 1.0000 Uiso R . . . . .
H202 H 0.8086 0.6826 0.8317 0.0328 1.0000 Uiso R . . . . .
H241 H 0.9061 0.3833 1.0140 0.0312 1.0000 Uiso R . . . . .
H251 H 0.9655 0.1326 1.0522 0.0358 1.0000 Uiso R . . . . .
H261 H 0.8845 -0.0708 0.9429 0.0360 1.0000 Uiso R . . . . .
H271 H 0.7456 -0.0223 0.7936 0.0338 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.98(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C1 . 1.233(4) yes
O2 . C3 . 1.412(3) yes
O2 . C12 . 1.445(4) yes
N1 . C1 . 1.344(3) yes
N1 . C4 . 1.478(3) yes
N1 . C5 . 1.462(3) yes
N2 . C22 . 1.369(3) yes
N2 . C28 . 1.385(3) yes
N2 . H1 . 0.84(3) no
C1 . C2 . 1.504(4) yes
C2 . C3 . 1.524(4) yes
C2 . H21 . 0.979 no
C2 . H22 . 0.956 no
C3 . C4 . 1.568(3) yes
C3 . H31 . 0.986 no
C4 . C19 . 1.559(4) yes
C4 . C22 . 1.495(4) yes
C5 . C6 . 1.503(4) yes
C5 . H51 . 0.968 no
C5 . H52 . 0.966 no
C6 . C7 . 1.388(4) yes
C6 . C11 . 1.389(5) yes
C7 . C8 . 1.400(5) yes
C7 . H71 . 0.931 no
C8 . C9 . 1.358(7) yes
C8 . H81 . 0.932 no
C9 . C10 . 1.367(6) yes
C9 . H91 . 0.933 no
C10 . C11 . 1.375(5) yes
C10 . H101 . 0.923 no
C11 . H111 . 0.944 no
C12 . C13 . 1.510(5) yes
C12 . H121 . 0.967 no
C12 . H122 . 0.980 no
C13 . C14 . 1.385(5) yes
C13 . C18 . 1.385(5) yes
C14 . C15 . 1.393(6) yes
C14 . H141 . 0.942 no
C15 . C16 . 1.380(6) yes
C15 . H151 . 0.934 no
C16 . C17 . 1.369(6) yes
C16 . H161 . 0.932 no
C17 . C18 . 1.384(6) yes
C17 . H171 . 0.945 no
C18 . H181 . 0.968 no
C19 . C20 . 1.566(4) yes
C19 . H191 . 0.953 no
C19 . H192 . 0.962 no
C20 . C21 . 1.498(4) yes
C20 . H201 . 0.971 no
C20 . H202 . 0.960 no
C21 . C22 . 1.351(4) yes
C21 . C23 . 1.435(4) yes
C23 . C24 . 1.403(4) yes
C23 . C28 . 1.420(4) yes
C24 . C25 . 1.374(4) yes
C24 . H241 . 0.938 no
C25 . C26 . 1.401(4) yes
C25 . H251 . 0.950 no
C26 . C27 . 1.383(4) yes
C26 . H261 . 0.946 no
C27 . C28 . 1.389(4) yes
C27 . H271 . 0.936 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 . O2 . C12 . 115.5(2) yes
C1 . N1 . C4 . 113.9(2) yes
C1 . N1 . C5 . 122.9(2) yes
C4 . N1 . C5 . 123.1(2) yes
C22 . N2 . C28 . 106.5(2) yes
C22 . N2 . H1 . 125(2) no
C28 . N2 . H1 . 127(2) no
N1 . C1 . O1 . 124.9(3) yes
N1 . C1 . C2 . 108.4(2) yes
O1 . C1 . C2 . 126.8(3) yes
C1 . C2 . C3 . 103.0(2) yes
C1 . C2 . H21 . 112.1 no
C3 . C2 . H21 . 108.1 no
C1 . C2 . H22 . 110.8 no
C3 . C2 . H22 . 112.6 no
H21 . C2 . H22 . 110.0 no
C2 . C3 . O2 . 108.9(2) yes
C2 . C3 . C4 . 102.9(2) yes
O2 . C3 . C4 . 116.1(2) yes
C2 . C3 . H31 . 109.0 no
O2 . C3 . H31 . 111.4 no
C4 . C3 . H31 . 108.0 no
C3 . C4 . N1 . 99.51(19) yes
C3 . C4 . C19 . 113.7(2) yes
N1 . C4 . C19 . 114.4(2) yes
C3 . C4 . C22 . 117.0(2) yes
N1 . C4 . C22 . 111.9(2) yes
C19 . C4 . C22 . 101.01(19) yes
N1 . C5 . C6 . 114.1(2) yes
N1 . C5 . H51 . 108.0 no
C6 . C5 . H51 . 110.0 no
N1 . C5 . H52 . 107.0 no
C6 . C5 . H52 . 109.3 no
H51 . C5 . H52 . 108.2 no
C5 . C6 . C7 . 121.0(3) yes
C5 . C6 . C11 . 120.6(3) yes
C7 . C6 . C11 . 118.4(3) yes
C6 . C7 . C8 . 119.4(4) yes
C6 . C7 . H71 . 119.3 no
C8 . C7 . H71 . 121.3 no
C7 . C8 . C9 . 121.0(4) yes
C7 . C8 . H81 . 119.3 no
C9 . C8 . H81 . 119.7 no
C8 . C9 . C10 . 119.9(4) yes
C8 . C9 . H91 . 120.1 no
C10 . C9 . H91 . 120.0 no
C9 . C10 . C11 . 120.2(4) yes
C9 . C10 . H101 . 119.6 no
C11 . C10 . H101 . 120.2 no
C6 . C11 . C10 . 121.1(4) yes
C6 . C11 . H111 . 118.8 no
C10 . C11 . H111 . 120.1 no
O2 . C12 . C13 . 112.9(2) yes
O2 . C12 . H121 . 107.3 no
C13 . C12 . H121 . 108.0 no
O2 . C12 . H122 . 109.1 no
C13 . C12 . H122 . 109.9 no
H121 . C12 . H122 . 109.6 no
C12 . C13 . C14 . 120.5(3) yes
C12 . C13 . C18 . 120.7(3) yes
C14 . C13 . C18 . 118.9(3) yes
C13 . C14 . C15 . 120.0(4) yes
C13 . C14 . H141 . 121.0 no
C15 . C14 . H141 . 119.0 no
C14 . C15 . C16 . 119.7(4) yes
C14 . C15 . H151 . 120.4 no
C16 . C15 . H151 . 119.9 no
C15 . C16 . C17 . 121.0(4) yes
C15 . C16 . H161 . 119.0 no
C17 . C16 . H161 . 120.0 no
C16 . C17 . C18 . 119.0(4) yes
C16 . C17 . H171 . 119.2 no
C18 . C17 . H171 . 121.8 no
C13 . C18 . C17 . 121.4(4) yes
C13 . C18 . H181 . 119.7 no
C17 . C18 . H181 . 119.0 no
C4 . C19 . C20 . 109.5(2) yes
C4 . C19 . H191 . 109.3 no
C20 . C19 . H191 . 110.9 no
C4 . C19 . H192 . 108.1 no
C20 . C19 . H192 . 110.6 no
H191 . C19 . H192 . 108.3 no
C19 . C20 . C21 . 101.9(2) yes
C19 . C20 . H201 . 112.5 no
C21 . C20 . H201 . 113.0 no
C19 . C20 . H202 . 110.1 no
C21 . C20 . H202 . 110.2 no
H201 . C20 . H202 . 109.0 no
C20 . C21 . C22 . 112.5(2) yes
C20 . C21 . C23 . 140.9(3) yes
C22 . C21 . C23 . 106.6(2) yes
C4 . C22 . N2 . 132.8(2) yes
C4 . C22 . C21 . 114.9(2) yes
N2 . C22 . C21 . 112.2(2) yes
C21 . C23 . C24 . 135.8(3) yes
C21 . C23 . C28 . 105.7(2) yes
C24 . C23 . C28 . 118.5(3) yes
C23 . C24 . C25 . 119.5(3) yes
C23 . C24 . H241 . 120.0 no
C25 . C24 . H241 . 120.5 no
C24 . C25 . C26 . 120.9(2) yes
C24 . C25 . H251 . 118.8 no
C26 . C25 . H251 . 120.2 no
C25 . C26 . C27 . 121.3(3) yes
C25 . C26 . H261 . 119.9 no
C27 . C26 . H261 . 118.8 no
C26 . C27 . C28 . 117.8(3) yes
C26 . C27 . H271 . 121.3 no
C28 . C27 . H271 . 120.9 no
C23 . C28 . C27 . 122.0(2) yes
C23 . C28 . N2 . 108.9(2) yes
C27 . C28 . N2 . 129.1(2) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N2 . H1 . O1 2_646 173(3) 0.84(3) 1.95(3) 2.790(5) yes

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
C12 O2 C3 C2 174.8(2) . . . . no
C12 O2 C3 C4 -69.7(3) . . . . no
C3 O2 C12 C13 -58.3(3) . . . . no
C4 N1 C1 O1 177.1(3) . . . . no
C4 N1 C1 C2 -3.4(4) . . . . no
C5 N1 C1 O1 -0.3(5) . . . . no
C5 N1 C1 C2 179.2(3) . . . . no
C1 N1 C4 C3 23.5(3) . . . . no
C1 N1 C4 C19 -98.2(3) . . . . no
C1 N1 C4 C22 147.8(3) . . . . no
C5 N1 C4 C3 -159.2(2) . . . . no
C5 N1 C4 C19 79.2(3) . . . . no
C5 N1 C4 C22 -34.8(3) . . . . no
C1 N1 C5 C6 109.5(3) . . . . no
C4 N1 C5 C6 -67.7(3) . . . . no
C28 N2 C22 C4 178.7(2) . . . . no
C28 N2 C22 C21 2.8(3) . . . . no
C22 N2 C28 C23 -2.0(3) . . . . no
C22 N2 C28 C27 177.4(2) . . . . no
O1 C1 C2 C3 160.4(3) . . . . no
N1 C1 C2 C3 -19.1(3) . . . . no
C1 C2 C3 O2 156.2(2) . . . . no
C1 C2 C3 C4 32.4(3) . . . . no
O2 C3 C4 N1 -152.1(2) . . . . no
O2 C3 C4 C19 -30.0(3) . . . . no
O2 C3 C4 C22 87.3(3) . . . . no
C2 C3 C4 N1 -33.2(2) . . . . no
C2 C3 C4 C19 88.9(2) . . . . no
C2 C3 C4 C22 -153.9(2) . . . . no
N1 C4 C19 C20 -116.0(2) . . . . no
C3 C4 C19 C20 130.6(2) . . . . no
C22 C4 C19 C20 4.3(3) . . . . no
N1 C4 C22 N2 -55.6(3) . . . . no
N1 C4 C22 C21 120.3(2) . . . . no
C3 C4 C22 N2 58.3(4) . . . . no
C3 C4 C22 C21 -125.9(2) . . . . no
C19 C4 C22 N2 -177.7(3) . . . . no
C19 C4 C22 C21 -1.8(3) . . . . no
N1 C5 C6 C7 114.1(3) . . . . no
N1 C5 C6 C11 -66.0(3) . . . . no
C5 C6 C7 C8 179.3(3) . . . . no
C11 C6 C7 C8 -0.6(5) . . . . no
C5 C6 C11 C10 179.5(3) . . . . no
C7 C6 C11 C10 -0.7(5) . . . . no
C6 C7 C8 C9 1.0(6) . . . . no
C7 C8 C9 C10 -0.1(7) . . . . no
C8 C9 C10 C11 -1.2(7) . . . . no
C9 C10 C11 C6 1.6(6) . . . . no
O2 C12 C13 C14 -59.6(4) . . . . no
O2 C12 C13 C18 120.5(3) . . . . no
C12 C13 C14 C15 178.1(3) . . . . no
C18 C13 C14 C15 -2.0(5) . . . . no
C12 C13 C18 C17 -177.5(3) . . . . no
C14 C13 C18 C17 2.7(5) . . . . no
C13 C14 C15 C16 -0.4(5) . . . . no
C14 C15 C16 C17 2.3(6) . . . . no
C15 C16 C17 C18 -1.7(6) . . . . no
C16 C17 C18 C13 -0.8(6) . . . . no
C4 C19 C20 C21 -5.2(3) . . . . no
C19 C20 C21 C22 4.1(3) . . . . no
C19 C20 C21 C23 -179.6(3) . . . . no
C20 C21 C22 N2 175.2(2) . . . . no
C20 C21 C22 C4 -1.5(3) . . . . no
C23 C21 C22 N2 -2.4(3) . . . . no
C23 C21 C22 C4 -179.1(2) . . . . no
C20 C21 C23 C24 5.9(6) . . . . no
C20 C21 C23 C28 -175.4(3) . . . . no
C22 C21 C23 C24 -177.6(3) . . . . no
C22 C21 C23 C28 1.1(3) . . . . no
C21 C23 C24 C25 178.0(3) . . . . no
C28 C23 C24 C25 -0.5(3) . . . . no
C21 C23 C28 N2 0.6(3) . . . . no
C21 C23 C28 C27 -178.9(2) . . . . no
C24 C23 C28 N2 179.5(2) . . . . no
C24 C23 C28 C27 0.1(3) . . . . no
C23 C24 C25 C26 0.3(3) . . . . no
C24 C25 C26 C27 0.4(3) . . . . no
C25 C26 C27 C28 -0.8(3) . . . . no
C26 C27 C28 N2 -178.8(2) . . . . no
C26 C27 C28 C23 0.6(3) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 N2 2.790(3) . 2_656 no
N1 N2 3.191(3) . . no
N2 C5 3.391(4) . . no
N2 C18 3.174(5) . . no
C3 C14 3.549(4) . . no
C6 C22 3.536(4) . . no
C6 C19 3.326(4) . . no
C7 C20 3.475(4) . . no
C7 C21 3.489(5) . . no
C7 C10 3.444(6) . 2_746 no
C12 C19 3.402(4) . . no
C12 C22 3.367(4) . . no
C16 C24 3.560(5) . 2_647 no
C18 C22 3.428(5) . . no
C18 C28 3.513(5) . . no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 18/01/19 at 12:19:33
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S H(1,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) H   (  22,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) H   (  52,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 18/01/19 at 12:19:33
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;


#===END

####################################################################### 
# 
# 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_pyn1813SNQ
_database_code_depnum_ccdc_archive 'CCDC 2010554'
loop_
_audit_author_name
_audit_author_address
'Anthony Willis'
;Australian National University
Australia
;
_audit_update_record             
;
2020-06-18 deposited with the CCDC.	2020-11-11 downloaded from the CCDC.
;
_audit_creation_date             18-08-02
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'Z:\pyn1813SNQ\Tony_pyn1813SNQ_da At 16:25 on'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   9.2571(1)
_cell_length_b                   8.0452(1)
_cell_length_c                   16.5061(1)
_cell_angle_alpha                90
_cell_angle_beta                 98.6300(8)
_cell_angle_gamma                90
_cell_volume                     1215.38(2)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1 '
_symmetry_space_group_name_Hall  'P 2yb'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Si 0.2541 0.3302 6.2915 2.4386 3.0353 32.3337 1.9891 0.6785 1.5410 81.6937
1.1407 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C23 H34 Cl1 N1 O2 Si1 
# Dc =      1.15 Fooo =    452.00 Mu =     19.88 M =    420.07
# Found Formula = C23 H34 Cl1 N1 O2 Si1 
# Dc =      1.15 FOOO =    452.00 Mu =     19.88 M =    420.07

_chemical_formula_sum            'C23 H34 Cl N O2 Si'
_chemical_formula_moiety         'C23 H34 Cl N O2 Si'
_chemical_compound_source        ' from U of Wollongong '
_chemical_formula_weight         420.07


_cell_measurement_reflns_used    20010
_cell_measurement_theta_min      5
_cell_measurement_theta_max      74
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_min          0.067
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_max          0.225

_exptl_crystal_density_diffrn    1.148
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             452
_exptl_absorpt_coefficient_mu    1.988

# Sheldrick geometric approximatio 0.78 0.88 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_T_max  0.88
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
#_diffrn_ambient_temperature 150.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (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  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_measurement_method       'ω scans'


# If a reference occurs more than once, delete the author 
# and date from subsequent references. 

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'

_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            24328
_reflns_number_total             4229
_diffrn_reflns_av_R_equivalents  0.035
_diffrn_reflns_av_sigmaI/netI    0.0303

# Number of reflections without Friedels Law is 4229 
# Number of reflections with Friedels Law is 2633 
# Theoretical number of reflections is about 2466 


_diffrn_reflns_theta_min         4.832
_diffrn_reflns_theta_max         73.976
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        73.976
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_reflns_limit_h_min              -11
_reflns_limit_h_max              11
_reflns_limit_k_min              -9
_reflns_limit_k_max              7
_reflns_limit_l_min              0
_reflns_limit_l_max              20

_oxford_diffrn_Wilson_B_factor   3.00
_oxford_diffrn_Wilson_scale      0.02

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.28
_refine_diff_density_max         0.35


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns         4229
_refine_ls_number_restraints     1
_refine_ls_number_parameters     254
_oxford_refine_ls_R_factor_ref   0.0403
_refine_ls_wR_factor_ref         0.1072
_refine_ls_goodness_of_fit_ref   1.0007
_refine_ls_shift/su_max          0.0047760
_refine_ls_shift/su_mean         0.0011685


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4229
_refine_ls_R_factor_all          0.0403
_refine_ls_wR_factor_all         0.1072

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4181
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_gt          0.1066

_refine_ls_abs_structure_Flack   0.002(12)
_refine_ls_abs_structure_details 'Flack (1983), 1596 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.09P)² + 0.09P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_special_details          
# see also _refine_ls_hydrogen for refinement keywords.                         
;                                                                               


Hydrogen atoms, with the exception of those of the TBSO group, were 
observed in a difference electron density map.
H atoms were all included at calculated positions.
The H atoms were initially refined with soft restraints on the 
bond lengths and angles to regularise their geometry 
(C---H in the range 0.93--0.98Å\) and with
Uiso(H) in the range 1.2-1.5 times Ueq of the parent atom. 
and finally refined with riding constraints.



The largest peaks in the final difference electron density map 
were located near the Cl  and Si atoms.
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Cl1 Cl -0.02179(6) 0.73016(10) 0.58780(3) 0.0465 1.0000 Uani . . . . . .
Si1 Si 0.16510(5) 0.44449(10) 0.15513(3) 0.0373 1.0000 Uani . . . . . .
O1 O 0.59513(13) 0.5233(2) 0.41062(8) 0.0417 1.0000 Uani . . . . . .
O2 O 0.24047(12) 0.56177(18) 0.23243(7) 0.0323 1.0000 Uani . . . . . .
N1 N 0.40438(14) 0.7064(2) 0.38418(8) 0.0306 1.0000 Uani . . . . . .
C1 C 0.46572(17) 0.5543(3) 0.38740(9) 0.0325 1.0000 Uani . . . . . .
C2 C 0.34756(16) 0.4289(3) 0.35783(10) 0.0328 1.0000 Uani . . . . . .
C3 C 0.22208(16) 0.5363(2) 0.31557(9) 0.0296 1.0000 Uani . . . . . .
C4 C 0.24286(16) 0.7025(2) 0.36252(9) 0.0302 1.0000 Uani . . . . . .
C5 C 0.17425(17) 0.6920(2) 0.44188(10) 0.0328 1.0000 Uani . . . . . .
C6 C 0.00978(18) 0.7081(3) 0.42553(12) 0.0354 1.0000 Uani . . . . . .
C7 C -0.05933(19) 0.7779(3) 0.35713(13) 0.0423 1.0000 Uani . . . . . .
C8 C 0.0166(2) 0.8425(3) 0.28970(11) 0.0426 1.0000 Uani . . . . . .
C9 C 0.18273(19) 0.8542(3) 0.31353(10) 0.0355 1.0000 Uani . . . . . .
C10 C 0.48858(18) 0.8550(3) 0.40791(10) 0.0363 1.0000 Uani . . . . . .
C11 C 0.54349(16) 0.9445(3) 0.33768(11) 0.0343 1.0000 Uani . . . . . .
C12 C 0.5445(2) 0.8692(3) 0.26219(11) 0.0403 1.0000 Uani . . . . . .
C13 C 0.6000(2) 0.9530(3) 0.19986(13) 0.0497 1.0000 Uani . . . . . .
C14 C 0.6551(2) 1.1115(3) 0.21277(16) 0.0539 1.0000 Uani . . . . . .
C15 C 0.6552(2) 1.1887(3) 0.28800(16) 0.0493 1.0000 Uani . . . . . .
C16 C 0.59897(18) 1.1043(3) 0.34974(13) 0.0405 1.0000 Uani . . . . . .
C17 C -0.07234(19) 0.6351(3) 0.48770(12) 0.0424 1.0000 Uani . . . . . .
C18 C -0.0377(2) 0.4741(4) 0.13843(13) 0.0572 1.0000 Uani . . . . . .
C19 C 0.2031(4) 0.2199(3) 0.17656(17) 0.0650 1.0000 Uani . . . . . .
C20 C 0.2502(2) 0.5230(4) 0.06562(12) 0.0509 1.0000 Uani . . . . . .
C21 C 0.2397(3) 0.7137(4) 0.06139(17) 0.0686 1.0000 Uani . . . . . .
C22 C 0.4112(3) 0.4745(5) 0.07611(18) 0.0776 1.0000 Uani . . . . . .
C23 C 0.1678(4) 0.4469(6) -0.01399(14) 0.0901 1.0000 Uani . . . . . .
H21 H 0.3221 0.3745 0.4050 0.0395 1.0000 Uiso R . . . . .
H22 H 0.3811 0.3485 0.3220 0.0394 1.0000 Uiso R . . . . .
H31 H 0.1279 0.4856 0.3194 0.0331 1.0000 Uiso R . . . . .
H51 H 0.2150 0.7800 0.4776 0.0361 1.0000 Uiso R . . . . .
H52 H 0.1952 0.5835 0.4669 0.0376 1.0000 Uiso R . . . . .
H71 H -0.1624 0.7832 0.3516 0.0504 1.0000 Uiso R . . . . .
H81 H -0.0222 0.9528 0.2743 0.0507 1.0000 Uiso R . . . . .
H82 H -0.0045 0.7690 0.2421 0.0511 1.0000 Uiso R . . . . .
H91 H 0.2037 0.9549 0.3448 0.0403 1.0000 Uiso R . . . . .
H92 H 0.2263 0.8625 0.2639 0.0408 1.0000 Uiso R . . . . .
H101 H 0.5725 0.8187 0.4450 0.0431 1.0000 Uiso R . . . . .
H102 H 0.4320 0.9334 0.4337 0.0418 1.0000 Uiso R . . . . .
H121 H 0.5078 0.7628 0.2534 0.0482 1.0000 Uiso R . . . . .
H131 H 0.6010 0.9004 0.1489 0.0593 1.0000 Uiso R . . . . .
H141 H 0.6937 1.1651 0.1713 0.0640 1.0000 Uiso R . . . . .
H151 H 0.6930 1.2967 0.2959 0.0591 1.0000 Uiso R . . . . .
H161 H 0.5976 1.1569 0.3993 0.0482 1.0000 Uiso R . . . . .
H171 H -0.1763 0.6500 0.4723 0.0512 1.0000 Uiso R . . . . .
H172 H -0.0484 0.5203 0.4945 0.0510 1.0000 Uiso R . . . . .
H181 H -0.0653 0.5859 0.1198 0.0840 1.0000 Uiso R . . . . .
H182 H -0.0775 0.4534 0.1878 0.0844 1.0000 Uiso R . . . . .
H183 H -0.0796 0.3960 0.0980 0.0842 1.0000 Uiso R . . . . .
H191 H 0.3078 0.2021 0.1865 0.0956 1.0000 Uiso R . . . . .
H192 H 0.1635 0.1903 0.2248 0.0964 1.0000 Uiso R . . . . .
H193 H 0.1616 0.1549 0.1306 0.0964 1.0000 Uiso R . . . . .
H211 H 0.1390 0.7500 0.0560 0.1030 1.0000 Uiso R . . . . .
H212 H 0.2912 0.7570 0.1126 0.1038 1.0000 Uiso R . . . . .
H213 H 0.2868 0.7573 0.0162 0.1032 1.0000 Uiso R . . . . .
H221 H 0.4230 0.3565 0.0822 0.1156 1.0000 Uiso R . . . . .
H222 H 0.4680 0.5267 0.1254 0.1147 1.0000 Uiso R . . . . .
H223 H 0.4529 0.5106 0.0278 0.1160 1.0000 Uiso R . . . . .
H231 H 0.1826 0.3279 -0.0140 0.1347 1.0000 Uiso R . . . . .
H232 H 0.2068 0.4964 -0.0593 0.1343 1.0000 Uiso R . . . . .
H233 H 0.0644 0.4720 -0.0213 0.1343 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          7.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 . C17 . 1.817(2) yes
Si1 . O2 . 1.6547(13) yes
Si1 . C18 . 1.872(2) yes
Si1 . C19 . 1.865(3) yes
Si1 . C20 . 1.885(2) yes
O1 . C1 . 1.227(2) yes
O2 . C3 . 1.4226(18) yes
N1 . C1 . 1.347(2) yes
N1 . C4 . 1.4847(18) yes
N1 . C10 . 1.449(2) yes
C1 . C2 . 1.514(3) yes
C2 . C3 . 1.530(2) yes
C2 . H21 . 0.953 no
C2 . H22 . 0.959 no
C3 . C4 . 1.543(3) yes
C3 . H31 . 0.974 no
C4 . C5 . 1.541(2) yes
C4 . C9 . 1.522(2) yes
C5 . C6 . 1.511(2) yes
C5 . H51 . 0.961 no
C5 . H52 . 0.973 no
C6 . C7 . 1.335(3) yes
C6 . C17 . 1.487(3) yes
C7 . C8 . 1.496(3) yes
C7 . H71 . 0.946 no
C8 . C9 . 1.532(2) yes
C8 . H81 . 0.976 no
C8 . H82 . 0.980 no
C9 . H91 . 0.964 no
C9 . H92 . 0.969 no
C10 . C11 . 1.516(3) yes
C10 . H101 . 0.960 no
C10 . H102 . 0.959 no
C11 . C12 . 1.387(3) yes
C11 . C16 . 1.387(3) yes
C12 . C13 . 1.391(3) yes
C12 . H121 . 0.924 no
C13 . C14 . 1.378(4) yes
C13 . H131 . 0.943 no
C14 . C15 . 1.388(4) yes
C14 . H141 . 0.925 no
C15 . C16 . 1.389(3) yes
C15 . H151 . 0.938 no
C16 . H161 . 0.923 no
C17 . H171 . 0.965 no
C17 . H172 . 0.952 no
C18 . H181 . 0.973 no
C18 . H182 . 0.958 no
C18 . H183 . 0.955 no
C19 . H191 . 0.968 no
C19 . H192 . 0.955 no
C19 . H193 . 0.954 no
C20 . C21 . 1.538(4) yes
C20 . C22 . 1.526(4) yes
C20 . C23 . 1.544(3) yes
C21 . H211 . 0.968 no
C21 . H212 . 0.971 no
C21 . H213 . 0.984 no
C22 . H221 . 0.959 no
C22 . H222 . 0.993 no
C22 . H223 . 0.980 no
C23 . H231 . 0.968 no
C23 . H232 . 0.964 no
C23 . H233 . 0.967 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 . Si1 . C18 . 109.80(9) yes
O2 . Si1 . C19 . 111.13(10) yes
C18 . Si1 . C19 . 107.93(14) yes
O2 . Si1 . C20 . 103.65(9) yes
C18 . Si1 . C20 . 111.71(11) yes
C19 . Si1 . C20 . 112.60(14) yes
Si1 . O2 . C3 . 124.35(12) yes
C1 . N1 . C4 . 113.18(14) yes
C1 . N1 . C10 . 122.19(13) yes
C4 . N1 . C10 . 124.34(15) yes
N1 . C1 . O1 . 125.68(18) yes
N1 . C1 . C2 . 108.23(14) yes
O1 . C1 . C2 . 126.09(18) yes
C1 . C2 . C3 . 103.47(15) yes
C1 . C2 . H21 . 107.3 no
C3 . C2 . H21 . 111.6 no
C1 . C2 . H22 . 111.3 no
C3 . C2 . H22 . 113.2 no
H21 . C2 . H22 . 109.7 no
C2 . C3 . O2 . 109.18(13) yes
C2 . C3 . C4 . 103.40(13) yes
O2 . C3 . C4 . 109.64(14) yes
C2 . C3 . H31 . 111.1 no
O2 . C3 . H31 . 111.2 no
C4 . C3 . H31 . 112.1 no
C3 . C4 . N1 . 100.63(12) yes
C3 . C4 . C5 . 110.08(15) yes
N1 . C4 . C5 . 108.97(12) yes
C3 . C4 . C9 . 114.81(13) yes
N1 . C4 . C9 . 112.68(14) yes
C5 . C4 . C9 . 109.32(14) yes
C4 . C5 . C6 . 112.09(13) yes
C4 . C5 . H51 . 107.9 no
C6 . C5 . H51 . 109.7 no
C4 . C5 . H52 . 109.2 no
C6 . C5 . H52 . 106.5 no
H51 . C5 . H52 . 111.4 no
C5 . C6 . C7 . 121.94(17) yes
C5 . C6 . C17 . 116.66(17) yes
C7 . C6 . C17 . 121.34(17) yes
C6 . C7 . C8 . 123.79(16) yes
C6 . C7 . H71 . 116.7 no
C8 . C7 . H71 . 119.5 no
C7 . C8 . C9 . 113.33(15) yes
C7 . C8 . H81 . 108.3 no
C9 . C8 . H81 . 109.1 no
C7 . C8 . H82 . 109.1 no
C9 . C8 . H82 . 108.4 no
H81 . C8 . H82 . 108.5 no
C8 . C9 . C4 . 111.12(16) yes
C8 . C9 . H91 . 107.6 no
C4 . C9 . H91 . 111.2 no
C8 . C9 . H92 . 108.4 no
C4 . C9 . H92 . 109.8 no
H91 . C9 . H92 . 108.6 no
N1 . C10 . C11 . 114.45(14) yes
N1 . C10 . H101 . 105.8 no
C11 . C10 . H101 . 107.5 no
N1 . C10 . H102 . 110.8 no
C11 . C10 . H102 . 107.2 no
H101 . C10 . H102 . 111.2 no
C10 . C11 . C12 . 121.86(18) yes
C10 . C11 . C16 . 119.33(17) yes
C12 . C11 . C16 . 118.77(19) yes
C11 . C12 . C13 . 120.4(2) yes
C11 . C12 . H121 . 119.5 no
C13 . C12 . H121 . 120.1 no
C12 . C13 . C14 . 120.2(2) yes
C12 . C13 . H131 . 119.8 no
C14 . C13 . H131 . 120.0 no
C13 . C14 . C15 . 120.2(2) yes
C13 . C14 . H141 . 119.5 no
C15 . C14 . H141 . 120.4 no
C14 . C15 . C16 . 119.2(2) yes
C14 . C15 . H151 . 119.2 no
C16 . C15 . H151 . 121.6 no
C15 . C16 . C11 . 121.26(19) yes
C15 . C16 . H161 . 118.9 no
C11 . C16 . H161 . 119.9 no
Cl1 . C17 . C6 . 111.89(14) yes
Cl1 . C17 . H171 . 107.3 no
C6 . C17 . H171 . 111.3 no
Cl1 . C17 . H172 . 106.1 no
C6 . C17 . H172 . 109.3 no
H171 . C17 . H172 . 110.9 no
Si1 . C18 . H181 . 112.0 no
Si1 . C18 . H182 . 110.9 no
H181 . C18 . H182 . 108.3 no
Si1 . C18 . H183 . 108.2 no
H181 . C18 . H183 . 109.1 no
H182 . C18 . H183 . 108.2 no
Si1 . C19 . H191 . 109.3 no
Si1 . C19 . H192 . 108.3 no
H191 . C19 . H192 . 108.7 no
Si1 . C19 . H193 . 109.8 no
H191 . C19 . H193 . 109.1 no
H192 . C19 . H193 . 111.5 no
Si1 . C20 . C21 . 109.80(17) yes
Si1 . C20 . C22 . 109.95(18) yes
C21 . C20 . C22 . 108.4(3) yes
Si1 . C20 . C23 . 108.85(19) yes
C21 . C20 . C23 . 109.7(3) yes
C22 . C20 . C23 . 110.2(2) yes
C20 . C21 . H211 . 111.0 no
C20 . C21 . H212 . 107.4 no
H211 . C21 . H212 . 108.2 no
C20 . C21 . H213 . 111.0 no
H211 . C21 . H213 . 110.6 no
H212 . C21 . H213 . 108.4 no
C20 . C22 . H221 . 111.0 no
C20 . C22 . H222 . 111.9 no
H221 . C22 . H222 . 107.2 no
C20 . C22 . H223 . 109.2 no
H221 . C22 . H223 . 109.1 no
H222 . C22 . H223 . 108.4 no
C20 . C23 . H231 . 109.9 no
C20 . C23 . H232 . 107.5 no
H231 . C23 . H232 . 109.8 no
C20 . C23 . H233 . 112.2 no
H231 . C23 . H233 . 110.1 no
H232 . C23 . H233 . 107.2 no
loop_

_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C18 Si1 O2 C3 67.83(16) . . . . no
C19 Si1 O2 C3 -51.50(17) . . . . no
C20 Si1 O2 C3 -172.69(14) . . . . no
O2 Si1 C20 C21 -49.22(16) . . . . no
O2 Si1 C20 C22 69.9(2) . . . . no
O2 Si1 C20 C23 -169.3(2) . . . . no
C18 Si1 C20 C21 68.93(19) . . . . no
C18 Si1 C20 C22 -172.0(2) . . . . no
C18 Si1 C20 C23 -51.2(3) . . . . no
C19 Si1 C20 C21 -169.42(17) . . . . no
C19 Si1 C20 C22 -50.3(3) . . . . no
C19 Si1 C20 C23 70.5(2) . . . . no
Si1 O2 C3 C2 93.51(15) . . . . no
Si1 O2 C3 C4 -153.89(11) . . . . no
C4 N1 C1 O1 -173.41(15) . . . . no
C4 N1 C1 C2 6.37(17) . . . . no
C10 N1 C1 O1 0.7(2) . . . . no
C10 N1 C1 C2 -179.51(13) . . . . no
C1 N1 C4 C3 -24.79(16) . . . . no
C1 N1 C4 C5 90.91(15) . . . . no
C1 N1 C4 C9 -147.57(14) . . . . no
C10 N1 C4 C3 161.24(14) . . . . no
C10 N1 C4 C5 -83.06(18) . . . . no
C10 N1 C4 C9 38.5(2) . . . . no
C1 N1 C10 C11 93.99(19) . . . . no
C4 N1 C10 C11 -92.56(18) . . . . no
O1 C1 C2 C3 -164.97(15) . . . . no
N1 C1 C2 C3 15.25(16) . . . . no
C1 C2 C3 O2 87.08(15) . . . . no
C1 C2 C3 C4 -29.55(15) . . . . no
O2 C3 C4 N1 -84.13(13) . . . . no
O2 C3 C4 C5 160.99(12) . . . . no
O2 C3 C4 C9 37.14(17) . . . . no
C2 C3 C4 N1 32.19(14) . . . . no
C2 C3 C4 C5 -82.68(14) . . . . no
C2 C3 C4 C9 153.47(13) . . . . no
N1 C4 C5 C6 173.20(15) . . . . no
C3 C4 C5 C6 -77.34(17) . . . . no
C9 C4 C5 C6 49.65(19) . . . . no
N1 C4 C9 C8 177.92(14) . . . . no
C3 C4 C9 C8 63.49(18) . . . . no
C5 C4 C9 C8 -60.76(18) . . . . no
C4 C5 C6 C7 -20.9(3) . . . . no
C4 C5 C6 C17 156.28(17) . . . . no
C5 C6 C7 C8 1.6(4) . . . . no
C17 C6 C7 C8 -175.5(2) . . . . no
C5 C6 C17 Cl1 60.5(2) . . . . no
C7 C6 C17 Cl1 -122.3(2) . . . . no
C6 C7 C8 C9 -11.9(3) . . . . no
C7 C8 C9 C4 41.6(2) . . . . no
N1 C10 C11 C12 -15.2(2) . . . . no
N1 C10 C11 C16 166.96(16) . . . . no
C10 C11 C12 C13 -177.93(17) . . . . no
C16 C11 C12 C13 -0.1(3) . . . . no
C10 C11 C16 C15 177.70(17) . . . . no
C12 C11 C16 C15 -0.2(3) . . . . no
C11 C12 C13 C14 0.3(3) . . . . no
C12 C13 C14 C15 -0.2(3) . . . . no
C13 C14 C15 C16 -0.1(3) . . . . no
C14 C15 C16 C11 0.3(3) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cl1 C17 3.640(2) . 2_556 no
Cl1 C2 3.6426(18) . 2_556 no
Cl1 C3 3.5966(17) . 2_556 no
O1 C17 3.275(2) . 1_655 no
O2 N1 2.9647(18) . . no
O2 C8 3.298(2) . . no
C1 C12 3.417(3) . . no
C2 C19 3.517(3) . . no
C2 C16 3.514(3) . 1_545 no
C3 C7 3.402(3) . . no
C9 C12 3.578(3) . . no
C9 C11 3.382(2) . . no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 02/08/18 at 16:41:39
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   2,X'S) H   (  21,X'S) H   (  22,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) H   (  52,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  92,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) H   ( 183,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) H   ( 193,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 212,X'S) H   ( 213,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) H   ( 223,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 232,X'S) H   ( 233,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 02/08/18 at 16:41:39
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;


####################################################################### 
# 
# 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_pyn1811SNQ
_database_code_depnum_ccdc_archive 'CCDC 2010552'
loop_
_audit_author_name
_audit_author_address
'Anthony Willis'
;Australian National University
Australia
;
_audit_update_record             
;
2020-06-18 deposited with the CCDC.	2020-11-11 downloaded from the CCDC.
;
_audit_creation_date             18-08-07
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'Z:\pyn1811SNQ\Tony_pyn1811SNQ_da At 15:17 on'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   7.7020(1)
_cell_length_b                   11.2053(2)
_cell_length_c                   14.0796(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.9742(14)
_cell_angle_gamma                90
_cell_volume                     1214.94(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1 '
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Si 0.2541 0.3302 6.2915 2.4386 3.0353 32.3337 1.9891 0.6785 1.5410 81.6937
1.1407 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C23 H36 Cl1 F1 N1 O2 Si1 
# Dc =      1.21 Fooo =    472.00 Mu =     20.71 M =    441.08
# Found Formula = C23 H35 Cl1 F1 N1 O2 Si1 
# Dc =      1.20 FOOO =    472.00 Mu =     20.71 M =    440.07

_chemical_formula_sum            'C23 H35 Cl F N O2 Si'
_chemical_formula_moiety         'C23 H35 Cl F N O2 Si'
_chemical_compound_source        ' from U of Wollongong '
_chemical_formula_weight         440.07


_cell_measurement_reflns_used    11825
_cell_measurement_theta_min      5
_cell_measurement_theta_max      74
_cell_measurement_temperature    150

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.067
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_max          0.428

_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    2.071

# Sheldrick geometric approximatio 0.80 0.87 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.60
_exptl_absorpt_correction_T_max  0.87
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
#_diffrn_ambient_temperature 150.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (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  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_measurement_method       'ω scans'


# If a reference occurs more than once, delete the author 
# and date from subsequent references. 

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'

_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            24240
_reflns_number_total             4893
_diffrn_reflns_av_R_equivalents  0.049
_diffrn_reflns_av_sigmaI/netI    0.0572


# Number of reflections without Friedels Law is 4893 
# Number of reflections with Friedels Law is 2591 
# Theoretical number of reflections is about 2463 


_diffrn_reflns_theta_min         5.045
_diffrn_reflns_theta_max         73.913
_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        73.913
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              -13
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_oxford_diffrn_Wilson_B_factor   3.28
_oxford_diffrn_Wilson_scale      0.01

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.51
_refine_diff_density_max         0.48


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns         4893
_refine_ls_number_restraints     1
_refine_ls_number_parameters     263
_oxford_refine_ls_R_factor_ref   0.0524
_refine_ls_wR_factor_ref         0.1395
_refine_ls_goodness_of_fit_ref   1.0009
_refine_ls_shift/su_max          0.0010805
_refine_ls_shift/su_mean         0.0000639


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4893
_refine_ls_R_factor_all          0.0524
_refine_ls_wR_factor_all         0.1395

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4737
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_gt          0.1380

_refine_ls_abs_structure_Flack   -0.008(19)
_refine_ls_abs_structure_details 'Flack (1983), 2302 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.09P)² + 0.49P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_special_details          
# see also _refine_ls_hydrogen for refinement keywords.                         
;                                                                               
When the structure was solved, it was clear that there were no double-bonds
within the six-membered ring and that there was an additional atom
attached to C6 from what had been expected.
This atom could be a F or the O of a hydroxy group.
If refined as the latter, the displacement parameters seemed small
in comparison to those of adjacent atoms and no H atom could be located in a 
subsequent difference electron-density map.
F, therefore, seemed a more likely assignment.
Mass spectra obtained from other crystals in the sample
yielded a value of mass of 440.2184, a very good match with a calculated value
of 440.2188 for C₂₃H₃₆NO₂¹⁹FSi³⁵Cl.
F is therefore used in this structure refinement for this atom.


The displacement ellipsoids of C18, C19, C21 and C22 are all
elongated tangentially with regard to the O2---Si1 vector.
This suggests that there is some disorder in the packing of
the TBSO group.  Examination of a slant Fourier electron-density map 
shows that the electron-densities of these atoms are not 'peanut shaped', 
which would suggest 2 main locations for each atom, 
but, rather, there is an arc of electron-density
more consistent with there being a superposition of many possible sites, 
and that the highest probability is at the centre.

Hydrogen atoms, with the exception of those of the TBSO group, were 
observed in a difference electron density map.
H atoms were all included at calculated positions.
The H atoms were initially refined with soft restraints on the 
bond lengths and angles to regularise their geometry 
(C---H in the range 0.93--0.98Å\) and with
Uiso(H) in the range 1.2-1.5 times Ueq of the parent atom. 
and finally refined with riding constraints.



The largest peaks in the final difference electron density map 
were located near the Cl  and Si atoms.
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Cl1 Cl 0.18356(13) 0.78462(12) 0.73023(6) 0.0629 1.0000 Uani . . . . . .
Si1 Si 0.74903(10) 0.21420(13) 0.61199(6) 0.0524 1.0000 Uani . . . . . .
F1 F 0.3447(2) 0.53349(17) 0.67756(11) 0.0428 1.0000 Uani . . . . . .
O1 O 0.5371(2) 0.16721(18) 0.98248(14) 0.0379 1.0000 Uani . . . . . .
O2 O 0.7241(2) 0.2712(2) 0.71985(12) 0.0345 1.0000 Uani . . . . . .
N1 N 0.6184(3) 0.3449(2) 0.91738(14) 0.0258 1.0000 Uani . . . . . .
C1 C 0.5475(3) 0.2346(2) 0.91443(18) 0.0289 1.0000 Uani . . . . . .
C2 C 0.4813(3) 0.2117(3) 0.81479(18) 0.0347 1.0000 Uani . . . . . .
C3 C 0.5629(3) 0.3104(2) 0.75533(17) 0.0312 1.0000 Uani . . . . . .
C4 C 0.5901(3) 0.4135(2) 0.82834(16) 0.0281 1.0000 Uani . . . . . .
C5 C 0.4212(3) 0.4864(2) 0.83818(17) 0.0290 1.0000 Uani . . . . . .
C6 C 0.3898(4) 0.5858(3) 0.76619(18) 0.0357 1.0000 Uani . . . . . .
C7 C 0.5497(4) 0.6604(3) 0.7506(2) 0.0408 1.0000 Uani . . . . . .
C8 C 0.7074(4) 0.5813(3) 0.7284(2) 0.0411 1.0000 Uani . . . . . .
C9 C 0.7441(3) 0.4947(3) 0.80880(18) 0.0318 1.0000 Uani . . . . . .
C10 C 0.6695(3) 0.4003(2) 1.00750(16) 0.0274 1.0000 Uani . . . . . .
C11 C 0.8631(3) 0.4036(2) 1.02742(16) 0.0269 1.0000 Uani . . . . . .
C12 C 0.9718(3) 0.3105(2) 1.0029(2) 0.0353 1.0000 Uani . . . . . .
C13 C 1.1451(4) 0.3120(3) 1.0307(2) 0.0456 1.0000 Uani . . . . . .
C14 C 1.2119(3) 0.4065(3) 1.0817(2) 0.0433 1.0000 Uani . . . . . .
C15 C 1.1050(4) 0.5006(3) 1.1063(2) 0.0416 1.0000 Uani . . . . . .
C16 C 0.9315(3) 0.4983(3) 1.07883(19) 0.0336 1.0000 Uani . . . . . .
C17 C 0.2325(4) 0.6543(3) 0.7992(2) 0.0421 1.0000 Uani . . . . . .
C18 C 0.6422(9) 0.3144(9) 0.5225(3) 0.1641 1.0000 Uani . . . . . .
C19 C 0.6520(7) 0.0641(7) 0.6050(5) 0.1440 1.0000 Uani . . . . . .
C20 C 0.9894(3) 0.2076(3) 0.5947(2) 0.0413 1.0000 Uani . . . . . .
C21 C 1.0681(11) 0.3277(6) 0.6110(9) 0.1829 1.0000 Uani . . . . . .
C22 C 1.0708(6) 0.1237(8) 0.6640(4) 0.1341 1.0000 Uani . . . . . .
C23 C 1.0333(5) 0.1665(7) 0.4965(3) 0.1018 1.0000 Uani . . . . . .
H21 H 0.3558 0.2181 0.8113 0.0411 1.0000 Uiso R . . . . .
H22 H 0.5147 0.1336 0.7933 0.0406 1.0000 Uiso R . . . . .
H31 H 0.4847 0.3394 0.7037 0.0363 1.0000 Uiso R . . . . .
H51 H 0.4214 0.5216 0.9011 0.0344 1.0000 Uiso R . . . . .
H52 H 0.3252 0.4321 0.8342 0.0354 1.0000 Uiso R . . . . .
H71 H 0.5751 0.7068 0.8075 0.0490 1.0000 Uiso R . . . . .
H72 H 0.5250 0.7164 0.6986 0.0492 1.0000 Uiso R . . . . .
H81 H 0.8077 0.6326 0.7193 0.0487 1.0000 Uiso R . . . . .
H82 H 0.6822 0.5383 0.6701 0.0491 1.0000 Uiso R . . . . .
H91 H 0.7703 0.5383 0.8670 0.0382 1.0000 Uiso R . . . . .
H92 H 0.8433 0.4461 0.7939 0.0378 1.0000 Uiso R . . . . .
H101 H 0.6139 0.3551 1.0546 0.0323 1.0000 Uiso R . . . . .
H102 H 0.6244 0.4806 1.0094 0.0317 1.0000 Uiso R . . . . .
H121 H 0.9289 0.2458 0.9680 0.0421 1.0000 Uiso R . . . . .
H131 H 1.2177 0.2485 1.0136 0.0552 1.0000 Uiso R . . . . .
H141 H 1.3283 0.4056 1.0993 0.0514 1.0000 Uiso R . . . . .
H151 H 1.1493 0.5648 1.1403 0.0498 1.0000 Uiso R . . . . .
H161 H 0.8598 0.5608 1.0966 0.0409 1.0000 Uiso R . . . . .
H171 H 0.2564 0.6801 0.8633 0.0498 1.0000 Uiso R . . . . .
H172 H 0.1309 0.6032 0.7964 0.0507 1.0000 Uiso R . . . . .
H181 H 0.6650 0.2874 0.4598 0.2467 1.0000 Uiso R . . . . .
H182 H 0.6821 0.3940 0.5290 0.2470 1.0000 Uiso R . . . . .
H183 H 0.5195 0.3140 0.5312 0.2468 1.0000 Uiso R . . . . .
H191 H 0.6686 0.0320 0.5425 0.2158 1.0000 Uiso R . . . . .
H192 H 0.7043 0.0131 0.6521 0.2156 1.0000 Uiso R . . . . .
H193 H 0.5297 0.0705 0.6152 0.2158 1.0000 Uiso R . . . . .
H211 H 1.1978 0.3223 0.5915 0.2827 1.0000 Uiso R . . . . .
H212 H 1.0568 0.3486 0.6823 0.2829 1.0000 Uiso R . . . . .
H213 H 0.9977 0.3857 0.5683 0.2828 1.0000 Uiso R . . . . .
H221 H 1.1934 0.1206 0.6550 0.1998 1.0000 Uiso R . . . . .
H222 H 1.0456 0.1508 0.7267 0.2000 1.0000 Uiso R . . . . .
H223 H 1.0204 0.0465 0.6543 0.2001 1.0000 Uiso R . . . . .
H231 H 1.1558 0.1678 0.4896 0.1513 1.0000 Uiso R . . . . .
H232 H 0.9903 0.0879 0.4869 0.1517 1.0000 Uiso R . . . . .
H233 H 0.9799 0.2177 0.4499 0.1519 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          9.6(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 . C17 . 1.791(3) yes
Si1 . O2 . 1.6616(18) yes
Si1 . C18 . 1.868(6) yes
Si1 . C19 . 1.843(6) yes
Si1 . C20 . 1.873(3) yes
F1 . C6 . 1.417(3) yes
O1 . C1 . 1.224(3) yes
O2 . C3 . 1.416(3) yes
N1 . C1 . 1.351(3) yes
N1 . C4 . 1.483(3) yes
N1 . C10 . 1.461(3) yes
C1 . C2 . 1.507(3) yes
C2 . C3 . 1.529(4) yes
C2 . H21 . 0.970 no
C2 . H22 . 0.962 no
C3 . C4 . 1.558(3) yes
C3 . H31 . 0.991 no
C4 . C5 . 1.544(3) yes
C4 . C9 . 1.524(3) yes
C5 . C6 . 1.522(3) yes
C5 . H51 . 0.970 no
C5 . H52 . 0.959 no
C6 . C7 . 1.507(4) yes
C6 . C17 . 1.514(4) yes
C7 . C8 . 1.540(4) yes
C7 . H71 . 0.972 no
C7 . H72 . 0.981 no
C8 . C9 . 1.514(4) yes
C8 . H81 . 0.974 no
C8 . H82 . 0.968 no
C9 . H91 . 0.973 no
C9 . H92 . 0.964 no
C10 . C11 . 1.513(3) yes
C10 . H101 . 0.943 no
C10 . H102 . 0.965 no
C11 . C12 . 1.385(3) yes
C11 . C16 . 1.383(4) yes
C12 . C13 . 1.385(4) yes
C12 . H121 . 0.933 no
C13 . C14 . 1.373(5) yes
C13 . H131 . 0.939 no
C14 . C15 . 1.386(4) yes
C14 . H141 . 0.926 no
C15 . C16 . 1.385(4) yes
C15 . H151 . 0.926 no
C16 . H161 . 0.929 no
C17 . H171 . 0.962 no
C17 . H172 . 0.970 no
C18 . H181 . 0.953 no
C18 . H182 . 0.948 no
C18 . H183 . 0.955 no
C19 . H191 . 0.961 no
C19 . H192 . 0.959 no
C19 . H193 . 0.958 no
C20 . C21 . 1.492(7) yes
C20 . C22 . 1.486(6) yes
C20 . C23 . 1.501(5) yes
C21 . H211 . 1.042 no
C21 . H212 . 1.035 no
C21 . H213 . 1.032 no
C22 . H221 . 0.956 no
C22 . H222 . 0.957 no
C22 . H223 . 0.957 no
C23 . H231 . 0.950 no
C23 . H232 . 0.950 no
C23 . H233 . 0.959 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 . Si1 . C18 . 109.2(2) yes
O2 . Si1 . C19 . 110.3(2) yes
C18 . Si1 . C19 . 109.8(4) yes
O2 . Si1 . C20 . 105.33(11) yes
C18 . Si1 . C20 . 111.2(3) yes
C19 . Si1 . C20 . 111.0(2) yes
Si1 . O2 . C3 . 123.89(15) yes
C1 . N1 . C4 . 113.23(19) yes
C1 . N1 . C10 . 121.2(2) yes
C4 . N1 . C10 . 123.19(19) yes
N1 . C1 . O1 . 124.9(2) yes
N1 . C1 . C2 . 108.4(2) yes
O1 . C1 . C2 . 126.7(2) yes
C1 . C2 . C3 . 104.5(2) yes
C1 . C2 . H21 . 110.8 no
C3 . C2 . H21 . 109.7 no
C1 . C2 . H22 . 111.1 no
C3 . C2 . H22 . 111.8 no
H21 . C2 . H22 . 108.9 no
C2 . C3 . O2 . 109.8(2) yes
C2 . C3 . C4 . 103.13(19) yes
O2 . C3 . C4 . 110.74(19) yes
C2 . C3 . H31 . 112.8 no
O2 . C3 . H31 . 111.6 no
C4 . C3 . H31 . 108.4 no
C3 . C4 . N1 . 100.94(19) yes
C3 . C4 . C5 . 110.32(19) yes
N1 . C4 . C5 . 108.05(19) yes
C3 . C4 . C9 . 114.8(2) yes
N1 . C4 . C9 . 111.01(19) yes
C5 . C4 . C9 . 111.1(2) yes
C4 . C5 . C6 . 116.9(2) yes
C4 . C5 . H51 . 108.0 no
C6 . C5 . H51 . 108.0 no
C4 . C5 . H52 . 108.0 no
C6 . C5 . H52 . 108.2 no
H51 . C5 . H52 . 107.5 no
C5 . C6 . F1 . 108.5(2) yes
C5 . C6 . C7 . 112.4(2) yes
F1 . C6 . C7 . 106.8(2) yes
C5 . C6 . C17 . 106.6(2) yes
F1 . C6 . C17 . 107.1(2) yes
C7 . C6 . C17 . 115.1(3) yes
C6 . C7 . C8 . 111.1(2) yes
C6 . C7 . H71 . 109.2 no
C8 . C7 . H71 . 109.1 no
C6 . C7 . H72 . 108.4 no
C8 . C7 . H72 . 111.1 no
H71 . C7 . H72 . 107.9 no
C7 . C8 . C9 . 110.8(2) yes
C7 . C8 . H81 . 108.5 no
C9 . C8 . H81 . 109.7 no
C7 . C8 . H82 . 108.1 no
C9 . C8 . H82 . 110.3 no
H81 . C8 . H82 . 109.3 no
C4 . C9 . C8 . 112.4(2) yes
C4 . C9 . H91 . 107.4 no
C8 . C9 . H91 . 110.0 no
C4 . C9 . H92 . 108.9 no
C8 . C9 . H92 . 109.7 no
H91 . C9 . H92 . 108.3 no
N1 . C10 . C11 . 114.93(19) yes
N1 . C10 . H101 . 105.3 no
C11 . C10 . H101 . 109.9 no
N1 . C10 . H102 . 109.2 no
C11 . C10 . H102 . 109.1 no
H101 . C10 . H102 . 108.3 no
C10 . C11 . C12 . 122.2(2) yes
C10 . C11 . C16 . 118.7(2) yes
C12 . C11 . C16 . 118.8(2) yes
C11 . C12 . C13 . 120.3(3) yes
C11 . C12 . H121 . 120.4 no
C13 . C12 . H121 . 119.3 no
C12 . C13 . C14 . 120.5(3) yes
C12 . C13 . H131 . 119.6 no
C14 . C13 . H131 . 119.9 no
C13 . C14 . C15 . 119.9(3) yes
C13 . C14 . H141 . 119.0 no
C15 . C14 . H141 . 121.1 no
C14 . C15 . C16 . 119.4(3) yes
C14 . C15 . H151 . 120.4 no
C16 . C15 . H151 . 120.3 no
C15 . C16 . C11 . 121.1(3) yes
C15 . C16 . H161 . 119.0 no
C11 . C16 . H161 . 119.8 no
C6 . C17 . Cl1 . 114.1(2) yes
C6 . C17 . H171 . 107.4 no
Cl1 . C17 . H171 . 107.3 no
C6 . C17 . H172 . 109.7 no
Cl1 . C17 . H172 . 107.3 no
H171 . C17 . H172 . 111.0 no
Si1 . C18 . H181 . 110.4 no
Si1 . C18 . H182 . 111.2 no
H181 . C18 . H182 . 108.9 no
Si1 . C18 . H183 . 109.7 no
H181 . C18 . H183 . 108.4 no
H182 . C18 . H183 . 108.1 no
Si1 . C19 . H191 . 109.3 no
Si1 . C19 . H192 . 110.0 no
H191 . C19 . H192 . 110.4 no
Si1 . C19 . H193 . 108.8 no
H191 . C19 . H193 . 108.1 no
H192 . C19 . H193 . 110.1 no
Si1 . C20 . C21 . 110.1(3) yes
Si1 . C20 . C22 . 110.3(3) yes
C21 . C20 . C22 . 107.7(7) yes
Si1 . C20 . C23 . 111.8(2) yes
C21 . C20 . C23 . 108.7(5) yes
C22 . C20 . C23 . 108.1(4) yes
C20 . C21 . H211 . 107.2 no
C20 . C21 . H212 . 108.2 no
H211 . C21 . H212 . 111.4 no
C20 . C21 . H213 . 105.7 no
H211 . C21 . H213 . 112.2 no
H212 . C21 . H213 . 111.7 no
C20 . C22 . H221 . 110.0 no
C20 . C22 . H222 . 108.4 no
H221 . C22 . H222 . 110.5 no
C20 . C22 . H223 . 108.2 no
H221 . C22 . H223 . 110.4 no
H222 . C22 . H223 . 109.3 no
C20 . C23 . H231 . 109.2 no
C20 . C23 . H232 . 109.4 no
H231 . C23 . H232 . 110.1 no
C20 . C23 . H233 . 110.2 no
H231 . C23 . H233 . 109.7 no
H232 . C23 . H233 . 108.3 no


loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C18 Si1 O2 C3 49.4(3) . . . . no
C19 Si1 O2 C3 -71.4(3) . . . . no
C20 Si1 O2 C3 168.8(2) . . . . no
O2 Si1 C20 C21 -54.6(5) . . . . no
O2 Si1 C20 C22 64.2(4) . . . . no
O2 Si1 C20 C23 -175.5(4) . . . . no
C18 Si1 C20 C21 63.6(6) . . . . no
C18 Si1 C20 C22 -177.7(4) . . . . no
C18 Si1 C20 C23 -57.4(5) . . . . no
C19 Si1 C20 C21 -173.9(6) . . . . no
C19 Si1 C20 C22 -55.2(4) . . . . no
C19 Si1 C20 C23 65.2(4) . . . . no
Si1 O2 C3 C2 96.5(2) . . . . no
Si1 O2 C3 C4 -150.28(18) . . . . no
C4 N1 C1 O1 -171.4(2) . . . . no
C4 N1 C1 C2 7.3(3) . . . . no
C10 N1 C1 O1 -8.4(4) . . . . no
C10 N1 C1 C2 170.3(2) . . . . no
C1 N1 C4 C3 -24.2(3) . . . . no
C1 N1 C4 C5 91.6(2) . . . . no
C1 N1 C4 C9 -146.4(2) . . . . no
C10 N1 C4 C3 173.1(2) . . . . no
C10 N1 C4 C5 -71.1(3) . . . . no
C10 N1 C4 C9 50.9(3) . . . . no
C1 N1 C10 C11 105.4(3) . . . . no
C4 N1 C10 C11 -93.3(3) . . . . no
O1 C1 C2 C3 -167.8(2) . . . . no
N1 C1 C2 C3 13.5(3) . . . . no
C1 C2 C3 O2 90.7(2) . . . . no
C1 C2 C3 C4 -27.4(2) . . . . no
O2 C3 C4 N1 -87.1(2) . . . . no
O2 C3 C4 C5 158.82(19) . . . . no
O2 C3 C4 C9 32.4(3) . . . . no
C2 C3 C4 N1 30.4(2) . . . . no
C2 C3 C4 C5 -83.7(2) . . . . no
C2 C3 C4 C9 149.8(2) . . . . no
N1 C4 C5 C6 165.5(2) . . . . no
C3 C4 C5 C6 -85.1(3) . . . . no
C9 C4 C5 C6 43.5(3) . . . . no
N1 C4 C9 C8 -170.1(2) . . . . no
C3 C4 C9 C8 76.2(3) . . . . no
C5 C4 C9 C8 -49.8(3) . . . . no
C4 C5 C6 F1 73.0(3) . . . . no
C4 C5 C6 C7 -45.0(3) . . . . no
C4 C5 C6 C17 -171.9(2) . . . . no
F1 C6 C7 C8 -67.7(3) . . . . no
C5 C6 C7 C8 51.2(3) . . . . no
C17 C6 C7 C8 173.5(2) . . . . no
F1 C6 C17 Cl1 -69.4(3) . . . . no
C5 C6 C17 Cl1 174.61(19) . . . . no
C7 C6 C17 Cl1 49.3(3) . . . . no
C6 C7 C8 C9 -59.0(3) . . . . no
C7 C8 C9 C4 58.8(3) . . . . no
N1 C10 C11 C12 -37.8(3) . . . . no
N1 C10 C11 C16 147.7(2) . . . . no
C10 C11 C12 C13 -173.6(2) . . . . no
C16 C11 C12 C13 0.9(4) . . . . no
C10 C11 C16 C15 174.2(2) . . . . no
C12 C11 C16 C15 -0.5(4) . . . . no
C11 C12 C13 C14 -0.9(4) . . . . no
C12 C13 C14 C15 0.6(4) . . . . no
C13 C14 C15 C16 -0.2(4) . . . . no
C14 C15 C16 C11 0.1(4) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cl1 F1 3.169(2) . . no
F1 C3 3.195(3) . . no
F1 C21 3.266(8) . 1_455 no
O1 C10 3.392(3) . 2_647 no
O1 C5 3.249(3) . 2_647 no
O2 N1 3.026(3) . . no
C1 C12 3.580(3) . . no
C9 C11 3.356(3) . . no



_iucr_refine_instruction_details_constraints 
;
#
# Punched on 07/08/18 at 09:50:22
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   2,X'S) H   (  21,X'S) H   (  22,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) H   (  52,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  92,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) H   ( 183,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) H   ( 193,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 212,X'S) H   ( 213,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) H   ( 223,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 232,X'S) H   ( 233,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 07/08/18 at 09:50:22
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

# start Validation Reply Form 
_vrf_PLAT220_pyn1811SNQ          
; 
PROBLEM: Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range        6.8 Ratio  
RESPONSE: ... see refine special details.  There is a degree of disorder
of the packing of the TBSO group.   The Ueq for these atoms therefore
tend to be higher than for other C atoms.
;
_vrf_PLAT242_pyn1811SNQ          
; 
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of        C20 Check  
RESPONSE: ... see refine special details.  There is a degree of disorder
of the packing of the TBSO group, rotationally about the Si---O bond.  
Si1 and C20 are at the centre, so have lower Ueq's than their neighbours. 
;
# end Validation Reply Form


#===END

####################################################################### 
# 
# 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_pyn1812SNQ
_database_code_depnum_ccdc_archive 'CCDC 2010553'
loop_
_audit_author_name
_audit_author_address
'Anthony Willis'
;Australian National University
Australia
;
_audit_update_record             
;
2020-06-18 deposited with the CCDC.	2020-11-11 downloaded from the CCDC.
;
_audit_creation_date             18-08-17
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'Z:\pyn1812SNQ\Tony_pyn1812SNQ_da At 9:16 on '
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   11.0485(6)
_cell_length_b                   7.5574(3)
_cell_length_c                   14.9506(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.179(5)
_cell_angle_gamma                90
_cell_volume                     1186.03(10)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1 '
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Si 0.2541 0.3302 6.2915 2.4386 3.0353 32.3337 1.9891 0.6785 1.5410 81.6937
1.1407 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C23 H35 Cl1 F1 N1 O2 Si1 
# Dc =      1.23 Fooo =    472.00 Mu =     21.21 M =    440.07
# Found Formula = C23.00 H35.00 Cl1 F1 N1 O2 Si1 
# Dc =      1.23 FOOO =    472.00 Mu =     21.21 M =    440.07

_chemical_formula_sum            'C23 H35 Cl F N O2 Si'
_chemical_formula_moiety         'C23 H35 Cl F N O2 Si'
_chemical_compound_source        ' from U of Wollongong '
_chemical_formula_weight         440.07


_cell_measurement_reflns_used    7046
_cell_measurement_theta_min      4
_cell_measurement_theta_max      72
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.042
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_max          0.292

_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             471.999
_exptl_absorpt_coefficient_mu    2.121

# Sheldrick geometric approximatio 0.85 0.91 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_T_max  0.91
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
#_diffrn_ambient_temperature 150.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (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  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_measurement_method       'ω scans'


# If a reference occurs more than once, delete the author 
# and date from subsequent references. 

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'

_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            24051
_reflns_number_total             3918
_diffrn_reflns_av_R_equivalents  0.067
_diffrn_reflns_av_sigmaI/netI    0.0851


# Number of reflections without Friedels Law is 3918 
# Number of reflections with Friedels Law is 2596 
# Theoretical number of reflections is about 2413 


_diffrn_reflns_theta_min         4.212
_diffrn_reflns_theta_max         74.149
_diffrn_measured_fraction_theta_max 0.995

_diffrn_reflns_theta_full        74.149
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              -13
_reflns_limit_h_max              13
_reflns_limit_k_min              -6
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              18

_oxford_diffrn_Wilson_B_factor   3.00
_oxford_diffrn_Wilson_scale      0.02

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.33
_refine_diff_density_max         0.39


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns         3918
_refine_ls_number_restraints     23
_refine_ls_number_parameters     292
_oxford_refine_ls_R_factor_ref   0.0598
_refine_ls_wR_factor_ref         0.1504
_refine_ls_goodness_of_fit_ref   0.9961
_refine_ls_shift/su_max          0.0057235
_refine_ls_shift/su_mean         0.0003499


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3918
_refine_ls_R_factor_all          0.0598
_refine_ls_wR_factor_all         0.1504

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3617
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_gt          0.1436

_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_abs_structure_details 'Flack (1983), 1322 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.09P)² + 0.72P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_special_details          
# see also _refine_ls_hydrogen for refinement keywords.                         
;                                                                               
When the structure was solved, it was clear that there were no double-bonds
within the six-membered ring and that there was an additional atom
attached to C6 from what had been expected.
This atom could be a F or the O of a hydroxy group.
If refined as the latter, the displacement parameters seemed small
in comparison to those of adjacent atoms and no H atom could be located in a 
subsequent difference electron-density map.
F, therefore, seemed a more likely assignment, and parallels
the presence of F in another isomer in this reaction sequence (pyn1811SNQ).

Extreme elongation of some displacement ellipsoids and the presence of 
difference electron density peaks suggest there is disorder in the 
packing of the TBSO group.  
Two overlapping images of the group were identified.
The major sites have an occupancy of about 0.9 and the minor ones
have about 0.1.  
In addition, there appears to be some disorder in the location of the 
Cl atom, again in an approximate 9:1 ratio.
The minor sites were assigned isotropic displacement parameters
set at appropriate fixed values.  Distances and angles involving
the minor sites were restrained to best-match values obtained for the 
major sites.
The relative occupancies of the sites were refined.



Hydrogen atoms, with the exception of those of the TBSO group, were 
observed in a difference electron density map.
H atoms were all included at calculated positions
and ride on the atoms to which they are bonded.


The largest peaks in the final difference electron density map 
were located within the disorder or near the Cl atom.
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Cl1 Cl 0.8421(3) 0.2405(6) 0.40233(13) 0.0454 0.905(8) Uani . . P . . .
Cl91 Cl 0.892(2) 0.273(2) 0.4301(14) 0.0450 0.095(8) Uiso D . P . . .
Si1 Si 0.43724(9) 0.2517(6) 0.74185(6) 0.0308 0.929(2) Uani . . P . . .
Si91 Si 0.4739(12) 0.3676(16) 0.8039(8) 0.0310 0.071(2) Uiso D . P . . .
F1 F 0.9661(2) 0.3950(7) 0.59557(16) 0.0442 1.0000 Uani . . . . . .
O1 O 0.6513(3) 0.8395(7) 0.5997(2) 0.0529 1.0000 Uani . . . . . .
O2 O 0.5434(3) 0.3919(7) 0.72680(19) 0.0322 0.929(2) Uani . . P . . .
O92 O 0.564(3) 0.452(4) 0.7370(18) 0.0320 0.071(2) Uiso D . P . . .
N1 N 0.7526(3) 0.5841(7) 0.66536(19) 0.0302 1.0000 Uani . . . . . .
C1 C 0.6492(4) 0.6818(8) 0.6163(3) 0.0378 1.0000 Uani . . . . . .
C2 C 0.5354(4) 0.5599(8) 0.5876(3) 0.0391 1.0000 Uani . . . . . .
C3 C 0.5785(3) 0.3921(8) 0.6436(2) 0.0326 1.0000 Uani D . . . . .
C4 C 0.7255(3) 0.3921(8) 0.6647(2) 0.0280 1.0000 Uani . . . . . .
C5 C 0.7527(3) 0.2974(8) 0.5814(2) 0.0292 1.0000 Uani . . . . . .
C6 C 0.8882(3) 0.2415(8) 0.5952(2) 0.0328 1.0000 Uani . . . . . .
C7 C 0.9466(4) 0.1527(8) 0.6868(3) 0.0397 1.0000 Uani . . . . . .
C8 C 0.9345(3) 0.2525(8) 0.7716(2) 0.0321 1.0000 Uani . . . . . .
C9 C 0.7949(3) 0.2993(8) 0.7579(2) 0.0298 1.0000 Uani . . . . . .
C10 C 0.8764(4) 0.6683(8) 0.6991(3) 0.0371 1.0000 Uani . . . . . .
C11 C 0.9130(3) 0.7402(8) 0.7975(2) 0.0307 1.0000 Uani . . . . . .
C12 C 0.8248(4) 0.7840(8) 0.8419(2) 0.0374 1.0000 Uani . . . . . .
C13 C 0.8638(4) 0.8634(9) 0.9302(3) 0.0480 1.0000 Uani . . . . . .
C14 C 0.9914(5) 0.8967(9) 0.9755(3) 0.0535 1.0000 Uani . . . . . .
C15 C 1.0789(4) 0.8495(9) 0.9319(3) 0.0531 1.0000 Uani . . . . . .
C16 C 1.0421(4) 0.7739(8) 0.8444(3) 0.0437 1.0000 Uani . . . . . .
C17 C 0.9033(4) 0.1287(8) 0.5159(3) 0.0395 1.0000 Uani D . . . . .
C18 C 0.5033(6) 0.0232(10) 0.7567(5) 0.0547 0.929(2) Uani . . P . . .
C19 C 0.2901(4) 0.2526(11) 0.6370(3) 0.0423 0.929(2) Uani . . P . . .
C20 C 0.4045(4) 0.3303(9) 0.8516(3) 0.0459 0.929(2) Uani . . P . . .
C21 C 0.5289(5) 0.3356(11) 0.9327(3) 0.0615 0.929(2) Uani . . P . . .
C22 C 0.3437(8) 0.5117(13) 0.8357(4) 0.0807 0.929(2) Uani . . P . . .
C23 C 0.3122(5) 0.1959(12) 0.8752(4) 0.0751 0.929(2) Uani . . P . . .
C918 C 0.580(4) 0.302(7) 0.923(2) 0.0500 0.071(2) Uiso D . P . . .
C919 C 0.361(5) 0.544(5) 0.815(4) 0.0500 0.071(2) Uiso D . P . . .
C920 C 0.388(4) 0.164(4) 0.745(2) 0.0500 0.071(2) Uiso D . P . . .
C921 C 0.485(6) 0.025(7) 0.740(7) 0.0700 0.071(2) Uiso D . P . . .
C922 C 0.308(8) 0.216(9) 0.647(3) 0.0700 0.071(2) Uiso D . P . . .
C923 C 0.303(6) 0.091(7) 0.799(4) 0.0700 0.071(2) Uiso D . P . . .
H21 H 0.4655 0.6111 0.6024 0.0470 1.0000 Uiso R . . . . .
H22 H 0.5113 0.5359 0.5220 0.0470 1.0000 Uiso R . . . . .
H31 H 0.5425 0.2922 0.6062 0.0391 0.929 Uiso R . . . . .
H32 H 0.5352 0.2866 0.6173 0.0391 0.071 Uiso R . . . . .
H51 H 0.7282 0.3754 0.5290 0.0351 1.0000 Uiso R . . . . .
H52 H 0.7011 0.1942 0.5677 0.0351 1.0000 Uiso R . . . . .
H71 H 1.0346 0.1365 0.6950 0.0478 1.0000 Uiso R . . . . .
H72 H 0.9069 0.0406 0.6848 0.0478 1.0000 Uiso R . . . . .
H81 H 0.9658 0.1807 0.8261 0.0386 1.0000 Uiso R . . . . .
H82 H 0.9831 0.3583 0.7795 0.0386 1.0000 Uiso R . . . . .
H91 H 0.7924 0.3753 0.8079 0.0358 1.0000 Uiso R . . . . .
H92 H 0.7506 0.1929 0.7608 0.0358 1.0000 Uiso R . . . . .
H101 H 0.9387 0.5835 0.6965 0.0445 1.0000 Uiso R . . . . .
H102 H 0.8772 0.7638 0.6579 0.0445 1.0000 Uiso R . . . . .
H121 H 0.7371 0.7599 0.8120 0.0449 1.0000 Uiso R . . . . .
H131 H 0.8022 0.8950 0.9598 0.0576 1.0000 Uiso R . . . . .
H141 H 1.0179 0.9513 1.0357 0.0643 1.0000 Uiso R . . . . .
H151 H 1.1669 0.8698 0.9631 0.0637 1.0000 Uiso R . . . . .
H161 H 1.1044 0.7440 0.8152 0.0525 1.0000 Uiso R . . . . .
H171 H 0.9912 0.1037 0.5276 0.0474 0.905 Uiso R . . . . .
H172 H 0.8580 0.0211 0.5136 0.0474 0.905 Uiso R . . . . .
H173 H 0.9839 0.0716 0.5339 0.0474 0.095 Uiso R . . . . .
H174 H 0.8377 0.0424 0.4971 0.0474 0.095 Uiso R . . . . .
H181 H 0.4414 -0.0566 0.7653 0.0658 0.929 Uiso R . . . . .
H182 H 0.5774 0.0192 0.8102 0.0658 0.929 Uiso R . . . . .
H183 H 0.5247 -0.0096 0.7022 0.0658 0.929 Uiso R . . . . .
H191 H 0.2300 0.1711 0.6469 0.0508 0.929 Uiso R . . . . .
H192 H 0.2542 0.3680 0.6284 0.0508 0.929 Uiso R . . . . .
H193 H 0.3115 0.2191 0.5826 0.0508 0.929 Uiso R . . . . .
H211 H 0.5126 0.3752 0.9881 0.0739 0.929 Uiso R . . . . .
H212 H 0.5650 0.2204 0.9429 0.0739 0.929 Uiso R . . . . .
H213 H 0.5866 0.4144 0.9176 0.0739 0.929 Uiso R . . . . .
H221 H 0.3276 0.5500 0.8915 0.0970 0.929 Uiso R . . . . .
H222 H 0.3995 0.5929 0.8201 0.0970 0.929 Uiso R . . . . .
H223 H 0.2657 0.5063 0.7856 0.0970 0.929 Uiso R . . . . .
H231 H 0.2943 0.2331 0.9305 0.0902 0.929 Uiso R . . . . .
H232 H 0.3507 0.0822 0.8853 0.0902 0.929 Uiso R . . . . .
H233 H 0.2351 0.1904 0.8242 0.0902 0.929 Uiso R . . . . .
H9181 H 0.5296 0.2567 0.9592 0.0600 0.071 Uiso R . . . . .
H9182 H 0.6257 0.4031 0.9542 0.0600 0.071 Uiso R . . . . .
H9183 H 0.6382 0.2144 0.9172 0.0600 0.071 Uiso R . . . . .
H9191 H 0.3104 0.5008 0.8517 0.0600 0.071 Uiso R . . . . .
H9192 H 0.4074 0.6448 0.8453 0.0600 0.071 Uiso R . . . . .
H9193 H 0.3069 0.5762 0.7544 0.0600 0.071 Uiso R . . . . .
H9211 H 0.4421 -0.0781 0.7101 0.0840 0.071 Uiso R . . . . .
H9212 H 0.5376 -0.0035 0.8018 0.0840 0.071 Uiso R . . . . .
H9213 H 0.5367 0.0701 0.7047 0.0840 0.071 Uiso R . . . . .
H9221 H 0.2637 0.1146 0.6152 0.0840 0.071 Uiso R . . . . .
H9222 H 0.2490 0.3043 0.6501 0.0840 0.071 Uiso R . . . . .
H9223 H 0.3620 0.2599 0.6132 0.0840 0.071 Uiso R . . . . .
H9231 H 0.2602 -0.0121 0.7681 0.0840 0.071 Uiso R . . . . .
H9232 H 0.3528 0.0610 0.8614 0.0840 0.071 Uiso R . . . . .
H9233 H 0.2413 0.1774 0.8014 0.0840 0.071 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          8.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 . C17 . 1.826(4) yes
Cl91 . C17 . 1.659(12) yes
Si1 . O2 . 1.648(3) yes
Si1 . C18 . 1.861(6) yes
Si1 . C19 . 1.873(4) yes
Si1 . C20 . 1.883(4) yes
Si91 . O92 . 1.736(17) yes
Si91 . C918 . 1.87(2) yes
Si91 . C919 . 1.87(2) yes
Si91 . C920 . 1.873(19) yes
F1 . C6 . 1.444(4) yes
O1 . C1 . 1.220(5) yes
O2 . C3 . 1.414(4) yes
O92 . C3 . 1.522(16) yes
N1 . C1 . 1.365(5) yes
N1 . C4 . 1.481(5) yes
N1 . C10 . 1.450(4) yes
C1 . C2 . 1.509(6) yes
C2 . C3 . 1.512(5) yes
C2 . H21 . 0.950 no
C2 . H22 . 0.950 no
C3 . C4 . 1.555(4) yes
C3 . H31 . 0.950 no
C3 . H32 . 0.950 no
C4 . C5 . 1.545(4) yes
C4 . C9 . 1.534(4) yes
C5 . C6 . 1.507(5) yes
C5 . H51 . 0.950 no
C5 . H52 . 0.950 no
C6 . C7 . 1.480(5) yes
C6 . C17 . 1.512(5) yes
C7 . C8 . 1.515(5) yes
C7 . H71 . 0.950 no
C7 . H72 . 0.950 no
C8 . C9 . 1.532(4) yes
C8 . H81 . 0.950 no
C8 . H82 . 0.950 no
C9 . H91 . 0.950 no
C9 . H92 . 0.950 no
C10 . C11 . 1.502(5) yes
C10 . H101 . 0.950 no
C10 . H102 . 0.950 no
C11 . C12 . 1.380(5) yes
C11 . C16 . 1.402(5) yes
C12 . C13 . 1.391(5) yes
C12 . H121 . 0.950 no
C13 . C14 . 1.383(6) yes
C13 . H131 . 0.950 no
C14 . C15 . 1.371(8) yes
C14 . H141 . 0.950 no
C15 . C16 . 1.369(6) yes
C15 . H151 . 0.950 no
C16 . H161 . 0.950 no
C17 . H171 . 0.950 no
C17 . H172 . 0.950 no
C17 . H173 . 0.950 no
C17 . H174 . 0.950 no
C18 . H181 . 0.950 no
C18 . H182 . 0.950 no
C18 . H183 . 0.950 no
C19 . H191 . 0.950 no
C19 . H192 . 0.950 no
C19 . H193 . 0.950 no
C20 . C21 . 1.523(6) yes
C20 . C22 . 1.513(8) yes
C20 . C23 . 1.556(8) yes
C21 . H211 . 0.950 no
C21 . H212 . 0.950 no
C21 . H213 . 0.950 no
C22 . H221 . 0.950 no
C22 . H222 . 0.950 no
C22 . H223 . 0.950 no
C23 . H231 . 0.950 no
C23 . H232 . 0.950 no
C23 . H233 . 0.950 no
C918 . H9181 . 0.950 no
C918 . H9182 . 0.950 no
C918 . H9183 . 0.950 no
C919 . H9191 . 0.950 no
C919 . H9192 . 0.950 no
C919 . H9193 . 0.950 no
C920 . C921 . 1.52(2) yes
C920 . C922 . 1.51(2) yes
C920 . C923 . 1.53(2) yes
C921 . H9211 . 0.950 no
C921 . H9212 . 0.950 no
C921 . H9213 . 0.950 no
C922 . H9221 . 0.950 no
C922 . H9222 . 0.950 no
C922 . H9223 . 0.950 no
C923 . H9231 . 0.950 no
C923 . H9232 . 0.950 no
C923 . H9233 . 0.950 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 . Si1 . C18 . 110.1(2) yes
O2 . Si1 . C19 . 110.6(2) yes
C18 . Si1 . C19 . 108.0(3) yes
O2 . Si1 . C20 . 104.8(2) yes
C18 . Si1 . C20 . 111.3(3) yes
C19 . Si1 . C20 . 112.0(2) yes
O92 . Si91 . C918 . 110.3(15) yes
O92 . Si91 . C919 . 108.1(16) yes
C918 . Si91 . C919 . 109.8(17) yes
O92 . Si91 . C920 . 109.0(12) yes
C918 . Si91 . C920 . 107.8(15) yes
C919 . Si91 . C920 . 111.9(16) yes
Si1 . O2 . C3 . 121.5(2) yes
Si91 . O92 . C3 . 131.7(13) yes
C1 . N1 . C4 . 113.1(3) yes
C1 . N1 . C10 . 119.3(3) yes
C4 . N1 . C10 . 126.8(3) yes
N1 . C1 . O1 . 124.9(4) yes
N1 . C1 . C2 . 107.8(3) yes
O1 . C1 . C2 . 127.3(4) yes
C1 . C2 . C3 . 105.3(3) yes
C1 . C2 . H21 . 110.5 no
C3 . C2 . H21 . 110.5 no
C1 . C2 . H22 . 110.5 no
C3 . C2 . H22 . 110.5 no
H21 . C2 . H22 . 109.5 no
O92 . C3 . C2 . 99.0(15) yes
C2 . C3 . O2 . 111.3(3) yes
O92 . C3 . C4 . 102.5(14) yes
C2 . C3 . C4 . 104.0(3) yes
O2 . C3 . C4 . 112.1(3) yes
C2 . C3 . H31 . 109.8 no
O2 . C3 . H31 . 109.8 no
C4 . C3 . H31 . 109.8 no
O92 . C3 . H32 . 116.3 no
C2 . C3 . H32 . 116.3 no
C4 . C3 . H32 . 116.3 no
C3 . C4 . N1 . 101.4(3) yes
C3 . C4 . C5 . 106.8(3) yes
N1 . C4 . C5 . 111.7(3) yes
C3 . C4 . C9 . 112.3(3) yes
N1 . C4 . C9 . 113.5(3) yes
C5 . C4 . C9 . 110.6(3) yes
C4 . C5 . C6 . 117.1(3) yes
C4 . C5 . H51 . 107.5 no
C6 . C5 . H51 . 107.5 no
C4 . C5 . H52 . 107.5 no
C6 . C5 . H52 . 107.6 no
H51 . C5 . H52 . 109.5 no
C5 . C6 . F1 . 109.9(3) yes
C5 . C6 . C7 . 112.4(3) yes
F1 . C6 . C7 . 105.9(3) yes
C5 . C6 . C17 . 113.5(3) yes
F1 . C6 . C17 . 104.1(3) yes
C7 . C6 . C17 . 110.4(3) yes
C6 . C7 . C8 . 114.9(3) yes
C6 . C7 . H71 . 108.1 no
C8 . C7 . H71 . 108.1 no
C6 . C7 . H72 . 108.1 no
C8 . C7 . H72 . 108.1 no
H71 . C7 . H72 . 109.5 no
C7 . C8 . C9 . 110.5(3) yes
C7 . C8 . H81 . 109.2 no
C9 . C8 . H81 . 109.2 no
C7 . C8 . H82 . 109.2 no
C9 . C8 . H82 . 109.2 no
H81 . C8 . H82 . 109.5 no
C4 . C9 . C8 . 115.1(3) yes
C4 . C9 . H91 . 108.0 no
C8 . C9 . H91 . 108.0 no
C4 . C9 . H92 . 108.0 no
C8 . C9 . H92 . 108.0 no
H91 . C9 . H92 . 109.5 no
N1 . C10 . C11 . 115.9(3) yes
N1 . C10 . H101 . 107.9 no
C11 . C10 . H101 . 107.9 no
N1 . C10 . H102 . 107.9 no
C11 . C10 . H102 . 107.9 no
H101 . C10 . H102 . 109.5 no
C10 . C11 . C12 . 122.9(3) yes
C10 . C11 . C16 . 118.5(3) yes
C12 . C11 . C16 . 118.5(3) yes
C11 . C12 . C13 . 120.3(4) yes
C11 . C12 . H121 . 119.9 no
C13 . C12 . H121 . 119.9 no
C12 . C13 . C14 . 120.6(4) yes
C12 . C13 . H131 . 119.7 no
C14 . C13 . H131 . 119.7 no
C13 . C14 . C15 . 118.9(4) yes
C13 . C14 . H141 . 120.6 no
C15 . C14 . H141 . 120.6 no
C14 . C15 . C16 . 121.3(4) yes
C14 . C15 . H151 . 119.4 no
C16 . C15 . H151 . 119.3 no
C11 . C16 . C15 . 120.4(4) yes
C11 . C16 . H161 . 119.8 no
C15 . C16 . H161 . 119.8 no
Cl1 . C17 . C6 . 111.6(3) yes
C6 . C17 . Cl91 . 103.6(7) yes
Cl1 . C17 . H171 . 108.9 no
C6 . C17 . H171 . 108.9 no
Cl1 . C17 . H172 . 108.9 no
C6 . C17 . H172 . 108.9 no
H171 . C17 . H172 . 109.5 no
C6 . C17 . H173 . 110.9 no
Cl91 . C17 . H173 . 110.9 no
C6 . C17 . H174 . 110.9 no
Cl91 . C17 . H174 . 110.9 no
H173 . C17 . H174 . 109.5 no
Si1 . C18 . H181 . 109.5 no
Si1 . C18 . H182 . 109.5 no
H181 . C18 . H182 . 109.5 no
Si1 . C18 . H183 . 109.5 no
H181 . C18 . H183 . 109.5 no
H182 . C18 . H183 . 109.5 no
Si1 . C19 . H191 . 109.5 no
Si1 . C19 . H192 . 109.5 no
H191 . C19 . H192 . 109.5 no
Si1 . C19 . H193 . 109.5 no
H191 . C19 . H193 . 109.5 no
H192 . C19 . H193 . 109.5 no
Si1 . C20 . C21 . 109.3(3) yes
Si1 . C20 . C22 . 110.2(3) yes
C21 . C20 . C22 . 110.3(5) yes
Si1 . C20 . C23 . 108.0(4) yes
C21 . C20 . C23 . 109.2(4) yes
C22 . C20 . C23 . 109.7(5) yes
C20 . C21 . H211 . 109.4 no
Si91 . C21 . H211 . 141.1 no
C20 . C21 . H212 . 109.5 no
Si91 . C21 . H212 . 105.8 no
H211 . C21 . H212 . 109.5 no
C20 . C21 . H213 . 109.5 no
Si91 . C21 . H213 . 72.3 no
H211 . C21 . H213 . 109.5 no
H212 . C21 . H213 . 109.5 no
C20 . C22 . H221 . 109.5 no
C20 . C22 . H222 . 109.5 no
H221 . C22 . H222 . 109.5 no
C20 . C22 . H223 . 109.5 no
H221 . C22 . H223 . 109.5 no
H222 . C22 . H223 . 109.5 no
C20 . C23 . H231 . 109.5 no
C20 . C23 . H232 . 109.5 no
H231 . C23 . H232 . 109.5 no
C20 . C23 . H233 . 109.5 no
H231 . C23 . H233 . 109.5 no
H232 . C23 . H233 . 109.5 no
Si91 . C918 . H9181 . 109.4 no
Si91 . C918 . H9182 . 109.4 no
H9181 . C918 . H9182 . 109.5 no
Si91 . C918 . H9183 . 109.5 no
H9181 . C918 . H9183 . 109.5 no
H9182 . C918 . H9183 . 109.5 no
Si91 . C919 . H9191 . 109.5 no
Si91 . C919 . H9192 . 109.5 no
H9191 . C919 . H9192 . 109.5 no
Si91 . C919 . H9193 . 109.4 no
H9191 . C919 . H9193 . 109.5 no
H9192 . C919 . H9193 . 109.5 no
Si91 . C920 . C921 . 109.3(18) yes
Si91 . C920 . C922 . 107.7(18) yes
C921 . C920 . C922 . 109.6(18) yes
Si91 . C920 . C923 . 110.9(17) yes
C921 . C920 . C923 . 109.7(18) yes
C922 . C920 . C923 . 109.7(18) yes
C920 . C921 . H9211 . 109.5 no
C920 . C921 . H9212 . 109.4 no
H9211 . C921 . H9212 . 109.5 no
C920 . C921 . H9213 . 109.5 no
H9211 . C921 . H9213 . 109.5 no
H9212 . C921 . H9213 . 109.5 no
C920 . C922 . H9221 . 109.5 no
C920 . C922 . H9222 . 109.5 no
H9221 . C922 . H9222 . 109.5 no
C920 . C922 . H9223 . 109.4 no
H9221 . C922 . H9223 . 109.5 no
H9222 . C922 . H9223 . 109.5 no
C920 . C923 . H9231 . 109.4 no
C920 . C923 . H9232 . 109.5 no
H9231 . C923 . H9232 . 109.5 no
C920 . C923 . H9233 . 109.4 no
H9231 . C923 . H9233 . 109.5 no
H9232 . C923 . H9233 . 109.5 no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C18 Si1 O2 C3 69.6(4) . . . . no
C19 Si1 O2 C3 -49.7(5) . . . . no
C20 Si1 O2 C3 -170.6(4) . . . . no
O2 Si1 C20 C21 -57.0(5) . . . . no
O2 Si1 C20 C22 64.4(5) . . . . no
O2 Si1 C20 C23 -175.8(4) . . . . no
C18 Si1 C20 C21 61.9(6) . . . . no
C18 Si1 C20 C22 -176.6(5) . . . . no
C18 Si1 C20 C23 -56.8(5) . . . . no
C19 Si1 C20 C21 -177.0(5) . . . . no
C19 Si1 C20 C22 -55.6(6) . . . . no
C19 Si1 C20 C23 64.2(5) . . . . no
Si1 O2 C3 C2 113.0(5) . . . . no
Si1 O2 C3 C4 -131.0(4) . . . . no
C4 N1 C1 O1 -172.9(4) . . . . no
C4 N1 C1 C2 7.1(4) . . . . no
C10 N1 C1 O1 -1.8(6) . . . . no
C10 N1 C1 C2 178.2(3) . . . . no
C1 N1 C4 C3 -22.6(4) . . . . no
C1 N1 C4 C5 90.9(4) . . . . no
C1 N1 C4 C9 -143.2(3) . . . . no
C10 N1 C4 C3 167.2(3) . . . . no
C10 N1 C4 C5 -79.4(4) . . . . no
C10 N1 C4 C9 46.6(5) . . . . no
C1 N1 C10 C11 93.0(5) . . . . no
C4 N1 C10 C11 -97.3(5) . . . . no
O1 C1 C2 C3 -167.8(4) . . . . no
N1 C1 C2 C3 12.2(5) . . . . no
C1 C2 C3 O2 95.6(4) . . . . no
C1 C2 C3 C4 -25.3(4) . . . . no
O2 C3 C4 N1 -92.0(5) . . . . no
O2 C3 C4 C5 151.0(5) . . . . no
O2 C3 C4 C9 29.5(7) . . . . no
C2 C3 C4 N1 28.3(3) . . . . no
C2 C3 C4 C5 -88.7(5) . . . . no
C2 C3 C4 C9 149.8(4) . . . . no
N1 C4 C5 C6 84.2(5) . . . . no
C3 C4 C5 C6 -165.8(5) . . . . no
C9 C4 C5 C6 -43.3(6) . . . . no
N1 C4 C9 C8 -80.5(5) . . . . no
C3 C4 C9 C8 165.2(4) . . . . no
C5 C4 C9 C8 46.0(6) . . . . no
C4 C5 C6 F1 -71.6(5) . . . . no
C4 C5 C6 C7 46.1(7) . . . . no
C4 C5 C6 C17 172.2(5) . . . . no
F1 C6 C7 C8 69.2(4) . . . . no
C5 C6 C7 C8 -50.9(6) . . . . no
C17 C6 C7 C8 -178.7(4) . . . . no
F1 C6 C17 Cl1 -62.9(4) . . . . no
C5 C6 C17 Cl1 56.7(5) . . . . no
C7 C6 C17 Cl1 -176.1(3) . . . . no
C6 C7 C8 C9 53.4(6) . . . . no
C7 C8 C9 C4 -51.3(6) . . . . no
N1 C10 C11 C12 -22.7(8) . . . . no
N1 C10 C11 C16 161.0(5) . . . . no
C10 C11 C12 C13 -174.8(6) . . . . no
C16 C11 C12 C13 1.5(8) . . . . no
C10 C11 C16 C15 176.0(6) . . . . no
C12 C11 C16 C15 -0.4(9) . . . . no
C11 C12 C13 C14 -1.2(9) . . . . no
C12 C13 C14 C15 -0.2(10) . . . . no
C13 C14 C15 C16 1.3(10) . . . . no
C14 C15 C16 C11 -1.0(9) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cl1 F1 3.020(4) . . no
Cl1 F1 3.357(6) . 2_746 no
Cl1 C919 3.64(5) . 2_646 no
Cl91 F1 3.338(18) . 2_746 no
Cl91 F1 2.53(2) . . no
Cl91 C17 3.443(19) . 2_756 no
Si1 C9 3.900(4) . . no
Si91 C9 3.852(14) . . no
F1 Cl91 2.53(2) . . no
F1 C10 2.933(7) . . no
F1 Cl91 3.338(18) . 2_756 no
F1 C17 3.079(6) . 2_756 no
F1 N1 3.199(5) . . no
O1 C2 3.357(6) . 2_656 no
O2 N1 3.102(5) . . no
O92 N1 2.81(3) . . no
C1 C12 3.414(5) . . no
C3 C922 3.29(9) . . no
C3 C921 3.43(7) . . no
C8 C10 3.321(8) . . no
C9 C11 3.560(8) . . no
C17 Cl91 3.443(19) . 2_746 no



_iucr_refine_instruction_details_constraints 
;
#
# Punched on 17/08/18 at 12:58:16
#
#LIST     12                                                                    
BLOCK SCALE X'S, CL(1,U'S,OCC) CL(91,U[ISO],OCC) 
CONT SI(1,U'S,OCC) SI(91,U[ISO],OCC) 
CONT F(1,U'S) 
CONT O(1,U'S) O(2,U'S,OCC) O(92,U[ISO],OCC) 
CONT N(1,U'S) UNTIL C(23) 
CONT C(18,OCC) UNTIL C(23) 
CONT C(918,U[ISO],OCC) UNTIL C(923) 
CONT ENANTIO 
FIX CL(91,U[ISO]) SI(91,U[ISO]) O(92,U[ISO]) 
CONT C(918,U[ISO]) UNTIL C(923) 
EQUIV CL(1,OCC) CL(91,OCC) 
WEIGHT -1  CL(91,OCC) 
EQUIV SI(1,OCC) O(2,OCC) C(18,OCC) UNTIL C(23) 
CONT SI(91,OCC) O(92,OCC) C(918,OCC) UNTIL C(923) 
WEIGHT -1 SI(91,OCC) O(92,OCC) C(918,OCC) UNTIL C(923) 
RIDE C   (   2,X'S) H   (  21,X'S) H   (  22,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) H(32,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) H   (  52,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  92,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) H(173,X'S) H(174,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) H   ( 183,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) H   ( 193,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 212,X'S) H   ( 213,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) H   ( 223,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 232,X'S) H   ( 233,X'S) 
RIDE C(  918,X'S) H( 9181,X'S) H( 9182,X'S) H   ( 9183,X'S) 
RIDE C(  919,X'S) H( 9191,X'S) H( 9192,X'S) H   ( 9193,X'S) 
RIDE C(  921,X'S) H( 9211,X'S) H( 9212,X'S) H   ( 9213,X'S) 
RIDE C(  922,X'S) H( 9221,X'S) H( 9222,X'S) H   ( 9223,X'S) 
RIDE C(  923,X'S) H( 9231,X'S) H( 9232,X'S) H   ( 9233,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 17/08/18 at 12:58:16
#
#LIST     16                                                                    
DIST 1.82, .02 = C(17) TO CL(91) 
REM 
DIST 1.41, .02 = C(3) TO O(92) 
DIST 1.65, .02 = O(92) TO SI(91) 
ANGLE 122 2 = C(3) TO O(92) TO SI(91) 
REM 
DIST 1.87, .02 = SI(91) TO C(918) 
DIST 1.87, .02 = SI(91) TO C(919) 
DIST 1.87, .02 = SI(91) TO C(920) 
ANGLE 110 2 = O(92) TO SI(91) TO C(918) 
ANGLE 110 2 = O(92) TO SI(91) TO C(919) 
ANGLE 110 2 = O(92) TO SI(91) TO C(920) 
ANGLE 110 2 = C(918) TO SI(91) TO C(919) 
ANGLE 110 2 = C(918) TO SI(91) TO C(920) 
ANGLE 110 2 = C(919) TO SI(91) TO C(920) 
DIST 1.52, .02 = C(920) TO C(921) 
DIST 1.52, .02 = C(920) TO C(922) 
DIST 1.52, .02 = C(920) TO C(923) 
ANGLE 110 2 = SI(91) TO C(920) TO C(921) 
ANGLE 110 2 = SI(91) TO C(920) TO C(922) 
ANGLE 110 2 = SI(91) TO C(920) TO C(923) 
ANGLE 110 2 = C(921) TO C(920) TO C(922) 
ANGLE 110 2 = C(921) TO C(920) TO C(923) 
ANGLE 110 2 = C(922) TO C(920) TO C(923) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;


#===END

