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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1a
_database_code_depnum_ccdc_archive 'CCDC 2079909'
loop_
_audit_author_name
_audit_author_address
'Louise Male'
;University of Birmingham
United Kingdom
;
_audit_update_record             
;
2021-04-25 deposited with the CCDC.	2021-06-18 downloaded from the CCDC.
;
_audit_creation_date             2019-04-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H29 N Si'
_chemical_formula_sum            'C21 H29 N Si'
_chemical_formula_weight         323.54
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H29 Si1 N1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.3498(4)
_cell_length_b                   7.3678(3)
_cell_length_c                   27.1186(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.469(4)
_cell_angle_gamma                90
_cell_volume                     1847.76(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2794
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.8550
_cell_measurement_theta_min      4.7460
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.093
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.849
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-6 0 -3 0.0331
6 0 3 0.0061
0 -5 -6 0.0978
0 5 5 0.1244
0 0 18 0.0154
0 0 -18 0.0154
-4 -3 10 0.0780
-4 0 14 0.0316

_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.049
_exptl_crystal_size_min          0.031
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-6.0003 0.0026 -2.9922 0.9300 -0.4304 0.1683
6.0003 -0.0026 2.9922 -0.9300 0.4304 -0.1683
-0.0149 -4.9934 -6.0029 -0.0667 0.0246 1.0979
0.0148 4.9943 5.0033 0.1020 0.0164 -1.0788
0.0024 -0.0164 17.9932 -0.6350 -0.7394 -0.3439
-0.0024 0.0164 -17.9932 0.6350 0.7394 0.3439
-4.0071 -3.0085 9.9976 0.0297 -0.9129 0.4729
-3.9981 -0.0128 13.9992 0.0556 -0.9441 -0.1935

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6721
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.051
_diffrn_reflns_theta_min         4.782
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00 -17.00   1.00    7.62    --  -42.31 -57.00-120.00   93
  2  ω   -103.00 -23.00   1.00    7.62    --  -42.31 -77.00   0.00   80
  3  ω    -25.00   2.00   1.00    7.62    --   42.31 -77.00 120.00   27
  4  ω     31.00  74.00   1.00    7.62    --   42.31 -77.00 120.00   43
  5  ω     66.00 119.00   1.00   30.48    --  106.63  15.00-150.00   53
  6  ω     84.00 176.00   1.00   30.48    --  106.63  30.00  90.00   92
  7  ω     33.00  97.00   1.00   30.48    --  106.63 -98.00 176.00   64
  8  ω     84.00 178.00   1.00   30.48    --  106.63  30.00  30.00   94
  9  ω     38.00 131.00   1.00   30.48    --  106.63 -45.00 150.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1374101000
_diffrn_orient_matrix_UB_12      0.0561112000
_diffrn_orient_matrix_UB_13      -0.0352213000
_diffrn_orient_matrix_UB_21      0.0922215000
_diffrn_orient_matrix_UB_22      0.0441556000
_diffrn_orient_matrix_UB_23      -0.0410628000
_diffrn_orient_matrix_UB_31      -0.0185080000
_diffrn_orient_matrix_UB_32      -0.1966202000
_diffrn_orient_matrix_UB_33      -0.0192866000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2932
_reflns_number_total             3490
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3490
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0581
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0552P)²+2.3546P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1456
_refine_ls_wR_factor_ref         0.1522
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H20A)=Sof(C22')=Sof(H22D)=Sof(H22E)=Sof(H22F)=1-FVAR(1)
 Sof(H20)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C14(H14), C17(H17), C20(H20), C20(H20A)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8)
3.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C22'(H22D,H22E,H22F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0927(3) 0.2438(4) 0.38799(10) 0.0331(6) Uani 1 1 d . . . . .
H1 H -0.075354 0.173245 0.416693 0.040 Uiso 1 1 calc R . . . .
C2 C -0.2206(3) 0.3383(4) 0.37634(11) 0.0376(7) Uani 1 1 d . . . . .
H2 H -0.288794 0.332406 0.398041 0.045 Uiso 1 1 calc R . . . .
C3 C -0.2511(3) 0.4424(4) 0.33315(11) 0.0371(7) Uani 1 1 d . . . . .
H3 H -0.339421 0.501844 0.325951 0.044 Uiso 1 1 calc R . . . .
C4 C -0.1500(3) 0.4571(4) 0.30112(10) 0.0317(6) Uani 1 1 d . . . . .
H4 H -0.169011 0.526929 0.272344 0.038 Uiso 1 1 calc R . . . .
C5 C 0.1424(3) 0.4432(4) 0.24549(10) 0.0338(6) Uani 1 1 d . . . . .
H5 H 0.073998 0.512768 0.225431 0.041 Uiso 1 1 calc R . . . .
C6 C 0.2797(4) 0.4204(4) 0.23317(10) 0.0396(7) Uani 1 1 d . . . . .
H6 H 0.303803 0.473544 0.204384 0.048 Uiso 1 1 calc R . . . .
C7 C 0.3825(3) 0.3174(4) 0.26396(10) 0.0363(6) Uani 1 1 d . . . . .
H7 H 0.474983 0.305356 0.255616 0.044 Uiso 1 1 calc R . . . .
C8 C 0.3498(3) 0.2333(4) 0.30648(10) 0.0310(6) Uani 1 1 d . . . . .
H8 H 0.419224 0.165637 0.326659 0.037 Uiso 1 1 calc R . . . .
C10 C 0.0102(3) 0.2565(3) 0.35565(9) 0.0242(5) Uani 1 1 d . . . . .
C11 C -0.0186(3) 0.3652(3) 0.31261(9) 0.0248(5) Uani 1 1 d . . . . .
C12 C 0.1084(3) 0.3603(3) 0.28847(9) 0.0251(5) Uani 1 1 d . . . . .
C13 C 0.2103(3) 0.2519(3) 0.31852(8) 0.0235(5) Uani 1 1 d . . . . .
C14 C 0.1032(3) -0.1074(4) 0.43611(10) 0.0303(6) Uani 1 1 d . . . . .
H14 H 0.039920 -0.021959 0.450276 0.036 Uiso 1 1 calc R . . . .
C15 C 0.0057(4) -0.2275(5) 0.39912(12) 0.0462(8) Uani 1 1 d . . . . .
H15A H -0.043941 -0.153561 0.372867 0.069 Uiso 1 1 calc GR . . . .
H15B H -0.063780 -0.288136 0.416122 0.069 Uiso 1 1 calc GR . . . .
H15C H 0.063626 -0.316042 0.385220 0.069 Uiso 1 1 calc GR . . . .
C16 C 0.1813(4) -0.2209(4) 0.47979(12) 0.0439(7) Uani 1 1 d . . . . .
H16A H 0.243301 -0.308122 0.467268 0.066 Uiso 1 1 calc GR . . . .
H16B H 0.111119 -0.283063 0.496103 0.066 Uiso 1 1 calc GR . . . .
H16C H 0.238203 -0.142268 0.503179 0.066 Uiso 1 1 calc GR . . . .
C17 C 0.3371(3) 0.1850(4) 0.45690(9) 0.0274(5) Uani 1 1 d . . . . .
H17 H 0.405333 0.109293 0.478845 0.033 Uiso 1 1 calc R . . . .
C18 C 0.2345(3) 0.2729(4) 0.48890(9) 0.0291(6) Uani 1 1 d . . . . .
H18A H 0.162000 0.341053 0.467955 0.044 Uiso 1 1 calc GR . . . .
H18B H 0.288231 0.352528 0.512823 0.044 Uiso 1 1 calc GR . . . .
H18C H 0.188971 0.180168 0.506019 0.044 Uiso 1 1 calc GR . . . .
C19 C 0.4245(3) 0.3323(5) 0.43486(11) 0.0461(8) Uani 1 1 d . . . . .
H19A H 0.491431 0.276492 0.415864 0.069 Uiso 1 1 calc GR . . . .
H19B H 0.476706 0.402834 0.461358 0.069 Uiso 1 1 calc GR . . . .
H19C H 0.359999 0.409910 0.413550 0.069 Uiso 1 1 calc GR . . . .
C20 C 0.3619(4) -0.1386(4) 0.38205(10) 0.0391(7) Uani 1 1 d . . . . .
H20 H 0.349603 -0.244267 0.402980 0.047 Uiso 0.84(2) 1 calc R . P A 1
H20A H 0.315669 -0.238740 0.397529 0.047 Uiso 0.16(2) 1 calc R . P A 2
C21 C 0.3113(4) -0.2146(4) 0.33034(11) 0.0427(7) Uani 1 1 d . . . . .
H21A H 0.208495 -0.232763 0.326050 0.064 Uiso 1 1 calc GR . . . .
H21B H 0.358498 -0.328421 0.326617 0.064 Uiso 1 1 calc GR . . . .
H21C H 0.334788 -0.130657 0.305679 0.064 Uiso 1 1 calc GR . . . .
C22 C 0.5253(5) -0.1104(12) 0.3930(2) 0.0393(17) Uani 0.84(2) 1 d . . P A 1
H22A H 0.552875 -0.014924 0.372224 0.059 Uiso 0.84(2) 1 calc GR . P A 1
H22B H 0.573618 -0.220616 0.386266 0.059 Uiso 0.84(2) 1 calc GR . P A 1
H22C H 0.552065 -0.077864 0.427403 0.059 Uiso 0.84(2) 1 calc GR . P A 1
C22' C 0.502(3) -0.184(5) 0.4105(17) 0.053(9) Uani 0.16(2) 1 d . . P A 2
H22D H 0.551503 -0.074162 0.422163 0.080 Uiso 0.16(2) 1 calc GR . P A 2
H22E H 0.558974 -0.248639 0.389555 0.080 Uiso 0.16(2) 1 calc GR . P A 2
H22F H 0.488448 -0.258141 0.438478 0.080 Uiso 0.16(2) 1 calc GR . P A 2
N1 N 0.1501(2) 0.1793(3) 0.35913(7) 0.0234(4) Uani 1 1 d . . . . .
Si1 Si 0.23876(7) 0.03301(9) 0.40689(2) 0.02279(19) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.380(4) . ?
C1 C10 1.397(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.394(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(4) . ?
C4 H4 0.9300 . ?
C4 C11 1.397(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(4) . ?
C5 C12 1.394(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.400(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.382(4) . ?
C8 H8 0.9300 . ?
C8 C13 1.397(4) . ?
C10 C11 1.409(3) . ?
C10 N1 1.416(3) . ?
C11 C12 1.438(4) . ?
C12 C13 1.407(3) . ?
C13 N1 1.413(3) . ?
C14 H14 0.9800 . ?
C14 C15 1.533(4) . ?
C14 C16 1.543(4) . ?
C14 Si1 1.898(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17 0.9800 . ?
C17 C18 1.529(4) . ?
C17 C19 1.532(4) . ?
C17 Si1 1.890(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20 0.9800 . ?
C20 H20A 0.9800 . ?
C20 C21 1.519(4) . ?
C20 C22 1.527(6) . ?
C20 C22' 1.46(3) . ?
C20 Si1 1.899(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22' H22D 0.9600 . ?
C22' H22E 0.9600 . ?
C22' H22F 0.9600 . ?
N1 Si1 1.792(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 120.8 . . ?
C2 C1 C10 118.4(3) . . ?
C10 C1 H1 120.8 . . ?
C1 C2 H2 118.9 . . ?
C1 C2 C3 122.2(3) . . ?
C3 C2 H2 118.9 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C11 118.9(3) . . ?
C11 C4 H4 120.5 . . ?
C6 C5 H5 120.6 . . ?
C6 C5 C12 118.9(3) . . ?
C12 C5 H5 120.6 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.1(3) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.6(3) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 H8 120.7 . . ?
C7 C8 C13 118.7(3) . . ?
C13 C8 H8 120.7 . . ?
C1 C10 C11 119.5(2) . . ?
C1 C10 N1 130.2(2) . . ?
C11 C10 N1 110.2(2) . . ?
C4 C11 C10 121.0(2) . . ?
C4 C11 C12 132.0(2) . . ?
C10 C11 C12 107.0(2) . . ?
C5 C12 C11 132.4(2) . . ?
C5 C12 C13 121.0(3) . . ?
C13 C12 C11 106.6(2) . . ?
C8 C13 C12 119.8(2) . . ?
C8 C13 N1 129.6(2) . . ?
C12 C13 N1 110.6(2) . . ?
C15 C14 H14 107.0 . . ?
C15 C14 C16 111.0(2) . . ?
C15 C14 Si1 114.26(19) . . ?
C16 C14 H14 107.0 . . ?
C16 C14 Si1 110.2(2) . . ?
Si1 C14 H14 107.0 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 H17 107.6 . . ?
C18 C17 C19 109.7(2) . . ?
C18 C17 Si1 112.26(18) . . ?
C19 C17 H17 107.6 . . ?
C19 C17 Si1 111.77(18) . . ?
Si1 C17 H17 107.6 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 H20 101.2 . . ?
C21 C20 H20A 91.2 . . ?
C21 C20 C22 113.4(3) . . ?
C21 C20 Si1 116.8(2) . . ?
C22 C20 H20 101.2 . . ?
C22 C20 Si1 118.8(3) . . ?
C22' C20 H20A 91.2 . . ?
C22' C20 C21 122.5(13) . . ?
C22' C20 Si1 120.6(12) . . ?
Si1 C20 H20 101.2 . . ?
Si1 C20 H20A 91.2 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C22' H22D 109.5 . . ?
C20 C22' H22E 109.5 . . ?
C20 C22' H22F 109.5 . . ?
H22D C22' H22E 109.5 . . ?
H22D C22' H22F 109.5 . . ?
H22E C22' H22F 109.5 . . ?
C10 N1 Si1 127.86(17) . . ?
C13 N1 C10 105.41(19) . . ?
C13 N1 Si1 126.60(17) . . ?
C14 Si1 C20 105.20(14) . . ?
C17 Si1 C14 107.92(11) . . ?
C17 Si1 C20 113.14(13) . . ?
N1 Si1 C14 111.32(11) . . ?
N1 Si1 C17 106.66(11) . . ?
N1 Si1 C20 112.59(11) . . ?

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
C1 C2 C3 C4 -1.7(4) . . . . ?
C1 C10 C11 C4 -1.6(4) . . . . ?
C1 C10 C11 C12 176.8(2) . . . . ?
C1 C10 N1 C13 -174.5(3) . . . . ?
C1 C10 N1 Si1 1.6(4) . . . . ?
C2 C1 C10 C11 0.4(4) . . . . ?
C2 C1 C10 N1 178.0(3) . . . . ?
C2 C3 C4 C11 0.5(4) . . . . ?
C3 C4 C11 C10 1.1(4) . . . . ?
C3 C4 C11 C12 -176.8(3) . . . . ?
C4 C11 C12 C5 -0.8(5) . . . . ?
C4 C11 C12 C13 176.8(3) . . . . ?
C5 C6 C7 C8 1.4(4) . . . . ?
C5 C12 C13 C8 2.9(4) . . . . ?
C5 C12 C13 N1 -178.6(2) . . . . ?
C6 C5 C12 C11 176.1(3) . . . . ?
C6 C5 C12 C13 -1.3(4) . . . . ?
C6 C7 C8 C13 0.2(4) . . . . ?
C7 C8 C13 C12 -2.3(4) . . . . ?
C7 C8 C13 N1 179.5(2) . . . . ?
C8 C13 N1 C10 174.2(3) . . . . ?
C8 C13 N1 Si1 -2.0(4) . . . . ?
C10 C1 C2 C3 1.3(4) . . . . ?
C10 C11 C12 C5 -178.9(3) . . . . ?
C10 C11 C12 C13 -1.3(3) . . . . ?
C10 N1 Si1 C14 28.9(2) . . . . ?
C10 N1 Si1 C17 -88.6(2) . . . . ?
C10 N1 Si1 C20 146.8(2) . . . . ?
C11 C10 N1 C13 3.3(3) . . . . ?
C11 C10 N1 Si1 179.40(17) . . . . ?
C11 C12 C13 C8 -175.1(2) . . . . ?
C11 C12 C13 N1 3.5(3) . . . . ?
C12 C5 C6 C7 -0.8(4) . . . . ?
C12 C13 N1 C10 -4.2(3) . . . . ?
C12 C13 N1 Si1 179.66(16) . . . . ?
C13 N1 Si1 C14 -155.7(2) . . . . ?
C13 N1 Si1 C17 86.8(2) . . . . ?
C13 N1 Si1 C20 -37.9(2) . . . . ?
C15 C14 Si1 C17 175.3(2) . . . . ?
C15 C14 Si1 C20 -63.6(2) . . . . ?
C15 C14 Si1 N1 58.6(2) . . . . ?
C16 C14 Si1 C17 -58.9(2) . . . . ?
C16 C14 Si1 C20 62.2(2) . . . . ?
C16 C14 Si1 N1 -175.60(18) . . . . ?
C18 C17 Si1 C14 -43.7(2) . . . . ?
C18 C17 Si1 C20 -159.71(19) . . . . ?
C18 C17 Si1 N1 76.0(2) . . . . ?
C19 C17 Si1 C14 -167.5(2) . . . . ?
C19 C17 Si1 C20 76.6(2) . . . . ?
C19 C17 Si1 N1 -47.7(2) . . . . ?
C21 C20 Si1 C14 85.3(3) . . . . ?
C21 C20 Si1 C17 -157.1(2) . . . . ?
C21 C20 Si1 N1 -36.1(3) . . . . ?
C22 C20 Si1 C14 -133.1(4) . . . . ?
C22 C20 Si1 C17 -15.5(4) . . . . ?
C22 C20 Si1 N1 105.5(4) . . . . ?
C22' C20 Si1 C14 -99(2) . . . . ?
C22' C20 Si1 C17 19(2) . . . . ?
C22' C20 Si1 N1 140(2) . . . . ?
N1 C10 C11 C4 -179.6(2) . . . . ?
N1 C10 C11 C12 -1.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.499
_oxdiff_exptl_absorpt_empirical_full_min 0.652
####################################################################### 
# 
# 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_12b
_database_code_depnum_ccdc_archive 'CCDC 2079912'
loop_
_audit_author_name
_audit_author_address
'Louise Male'
;University of Birmingham
United Kingdom
;
_audit_update_record             
;
2021-04-25 deposited with the CCDC.	2021-06-18 downloaded from the CCDC.
;
_audit_creation_date             2019-05-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H7 N Se2'
_chemical_formula_sum            'C12 H7 N Se2'
_chemical_formula_weight         323.11
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H7 N1 Se2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.9907(4)
_cell_length_b                   6.7480(3)
_cell_length_c                   14.9843(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.086(4)
_cell_angle_gamma                90
_cell_volume                     1006.22(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2853
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.3120
_cell_measurement_theta_min      5.0680
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.847
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.698
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark orange'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.133
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 0 -6 0.0265
-5 0 6 0.0265
3 1 8 0.0814
-4 -1 -6 0.0896
2 3 7 0.0793
0 4 2 0.0772
-3 3 -5 0.0590
-3 1 -8 0.0668
1 -4 -2 0.0621
3 -3 6 0.0632
2 3 -7 0.0479
3 4 -4 0.0587
3 3 5 0.0737
-3 -4 3 0.0578
-1 -3 7 0.0532
-6 0 5 0.0245
6 1 1 0.0648
5 1 -7 0.0265
6 -1 -1 0.0499

_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.053
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.9945 0.0055 -5.9986 0.1797 -0.9111 -0.1870
-4.9945 -0.0055 5.9986 -0.1797 0.9111 0.1870
3.0002 0.9975 7.9972 -0.0515 -0.0835 1.0041
-3.9989 -0.9989 -5.9979 -0.0104 0.2956 -0.8942
2.0007 2.9957 7.0014 0.4165 0.0750 0.9732
0.0008 3.9958 2.0059 0.8006 0.1919 0.4432
-2.9991 2.9980 -4.9918 0.8197 0.3128 -0.4703
-3.0001 1.0009 -7.9939 0.4841 0.1421 -0.8731
0.9985 -3.9953 -2.0061 -0.8035 -0.3293 -0.3719
2.9994 -2.9984 5.9914 -0.8520 -0.2754 0.5609
1.9966 3.0017 -6.9923 0.8698 -0.4486 -0.2950
2.9968 4.0002 -3.9922 0.9861 -0.4445 0.1136
2.9994 2.9971 5.0020 0.4783 -0.1372 0.8633
-2.9971 -3.9998 2.9927 -0.9537 0.4071 -0.2041
-0.9973 -3.0012 6.9920 -0.8727 0.3113 0.3663
-5.9941 -0.0057 4.9994 -0.1444 1.0110 0.0251
5.9959 1.0022 0.9996 0.1664 -0.7573 0.5839
4.9943 1.0051 -6.9965 0.4284 -0.9192 -0.2121
5.9952 -0.9952 -1.0029 -0.2015 -0.8907 0.2717

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3677
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.409
_diffrn_reflns_theta_min         5.119
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -109.00 -39.00   1.00    1.00    --  -42.56 -38.00 120.00   70
  2  ω    -59.00 -13.00   1.00    1.00    --  -42.56  38.00   0.00   46
  3  ω     21.00  82.00   1.00    1.00    --   42.56 -99.00 -30.00   61
  4  ω     57.00  97.00   1.00    1.00    --   42.56-125.00 120.00   40
  5  ω     88.00 174.00   1.00    1.00    --  106.63  61.00-120.00   86
  6  ω    112.00 176.00   1.00    1.00    --  106.63 125.00 120.00   64
  7  ω     31.00  84.00   1.00    1.00    --  106.63 -94.00  60.00   53
  8  ω     34.00 138.00   1.00    1.00    --  106.63 -77.00 120.00  104
  9  ω    128.00 176.00   1.00    1.00    --  106.63  45.00 120.00   48
 10  ω     26.00  60.00   1.00    1.00    --  106.63 -94.00 -60.00   34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0030566000
_diffrn_orient_matrix_UB_12      0.2165659000
_diffrn_orient_matrix_UB_13      -0.0322987000
_diffrn_orient_matrix_UB_21      -0.1374396000
_diffrn_orient_matrix_UB_22      0.0292462000
_diffrn_orient_matrix_UB_23      0.0374716000
_diffrn_orient_matrix_UB_31      0.0713354000
_diffrn_orient_matrix_UB_32      0.0653997000
_diffrn_orient_matrix_UB_33      0.0906326000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1875
_reflns_number_total             1999
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1999
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0215
_refine_ls_restrained_S_all      1.120
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0299P)²+0.3744P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0550
_refine_ls_wR_factor_ref         0.0561
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C7(H7), C8(H8)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3617(3) 0.2056(3) 0.55668(16) 0.0177(5) Uani 1 1 d . . . . .
H1 H 0.363533 0.192973 0.618576 0.021 Uiso 1 1 calc R . . . .
C2 C 0.2429(2) 0.1902(3) 0.50261(17) 0.0190(5) Uani 1 1 d . . . . .
H2 H 0.163306 0.170819 0.529197 0.023 Uiso 1 1 calc R . . . .
C3 C 0.2382(2) 0.2027(3) 0.40862(16) 0.0166(5) Uani 1 1 d . . . . .
H3 H 0.156858 0.188636 0.373895 0.020 Uiso 1 1 calc R . . . .
C4 C 0.3556(2) 0.2360(4) 0.36825(15) 0.0148(4) Uani 1 1 d . . . . .
C5 C 0.6625(2) 0.3565(3) 0.32100(15) 0.0147(4) Uani 1 1 d . . . . .
C6 C 0.7995(2) 0.3920(4) 0.32198(17) 0.0188(5) Uani 1 1 d . . . . .
H6 H 0.836637 0.428769 0.269700 0.023 Uiso 1 1 calc R . . . .
C7 C 0.8814(2) 0.3718(4) 0.40260(17) 0.0202(5) Uani 1 1 d . . . . .
H7 H 0.973437 0.392394 0.402240 0.024 Uiso 1 1 calc R . . . .
C8 C 0.8302(2) 0.3224(4) 0.48260(17) 0.0184(5) Uani 1 1 d . . . . .
H8 H 0.885979 0.311405 0.535463 0.022 Uiso 1 1 calc R . . . .
C10 C 0.4793(2) 0.2410(3) 0.51504(15) 0.0143(4) Uani 1 1 d . . . . .
C11 C 0.4757(2) 0.2634(3) 0.42145(15) 0.0123(4) Uani 1 1 d . . . . .
C12 C 0.6099(2) 0.3001(3) 0.40027(15) 0.0129(4) Uani 1 1 d . . . . .
C13 C 0.6926(2) 0.2899(3) 0.48118(16) 0.0148(5) Uani 1 1 d . . . . .
N1 N 0.6116(2) 0.2554(3) 0.54952(14) 0.0170(4) Uani 1 1 d . . . . .
H1A H 0.635(3) 0.239(5) 0.601(2) 0.022(8) Uiso 1 1 d . . . . .
Se1 Se 0.36686(2) 0.19840(4) 0.24225(2) 0.01770(9) Uani 1 1 d . . . . .
Se2 Se 0.53876(2) 0.42950(4) 0.22135(2) 0.01814(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.380(4) . ?
C1 C10 1.398(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.407(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(3) . ?
C4 C11 1.392(3) . ?
C4 Se1 1.918(2) . ?
C5 C6 1.388(3) . ?
C5 C12 1.394(3) . ?
C5 Se2 1.917(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.405(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.385(4) . ?
C8 H8 0.9300 . ?
C8 C13 1.391(3) . ?
C10 C11 1.408(3) . ?
C10 N1 1.379(3) . ?
C11 C12 1.427(3) . ?
C12 C13 1.407(3) . ?
C13 N1 1.380(3) . ?
N1 H1A 0.80(3) . ?
Se1 Se2 2.3611(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 121.2 . . ?
C2 C1 C10 117.6(2) . . ?
C10 C1 H1 121.2 . . ?
C1 C2 H2 118.9 . . ?
C1 C2 C3 122.3(2) . . ?
C3 C2 H2 118.9 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C11 119.4(2) . . ?
C3 C4 Se1 122.28(18) . . ?
C11 C4 Se1 117.31(17) . . ?
C6 C5 C12 118.9(2) . . ?
C6 C5 Se2 122.09(18) . . ?
C12 C5 Se2 117.92(17) . . ?
C5 C6 H6 120.3 . . ?
C5 C6 C7 119.4(2) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 H7 118.8 . . ?
C8 C7 C6 122.4(2) . . ?
C8 C7 H7 118.8 . . ?
C7 C8 H8 121.1 . . ?
C7 C8 C13 117.7(2) . . ?
C13 C8 H8 121.1 . . ?
C1 C10 C11 120.9(2) . . ?
N1 C10 C1 131.3(2) . . ?
N1 C10 C11 107.7(2) . . ?
C4 C11 C10 120.1(2) . . ?
C4 C11 C12 132.4(2) . . ?
C10 C11 C12 107.4(2) . . ?
C5 C12 C11 132.0(2) . . ?
C5 C12 C13 120.7(2) . . ?
C13 C12 C11 106.9(2) . . ?
C8 C13 C12 120.6(2) . . ?
N1 C13 C8 131.2(2) . . ?
N1 C13 C12 108.0(2) . . ?
C10 N1 C13 109.85(19) . . ?
C10 N1 H1A 123(2) . . ?
C13 N1 H1A 127(2) . . ?
C4 Se1 Se2 98.62(7) . . ?
C5 Se2 Se1 98.83(7) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A Se1 0.80(3) 3.02(3) 3.693(2) 143(3) 4_666 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
C1 C2 C3 C4 -1.5(4) . . . . ?
C1 C10 C11 C4 -4.8(3) . . . . ?
C1 C10 C11 C12 179.2(2) . . . . ?
C1 C10 N1 C13 179.3(2) . . . . ?
C2 C1 C10 C11 1.1(3) . . . . ?
C2 C1 C10 N1 -177.0(2) . . . . ?
C2 C3 C4 C11 -2.2(4) . . . . ?
C2 C3 C4 Se1 166.11(17) . . . . ?
C3 C4 C11 C10 5.3(3) . . . . ?
C3 C4 C11 C12 -179.9(2) . . . . ?
C4 C11 C12 C5 13.6(4) . . . . ?
C4 C11 C12 C13 -172.7(2) . . . . ?
C5 C6 C7 C8 -1.7(4) . . . . ?
C5 C12 C13 C8 -4.5(3) . . . . ?
C5 C12 C13 N1 172.5(2) . . . . ?
C6 C5 C12 C11 176.5(2) . . . . ?
C6 C5 C12 C13 3.5(3) . . . . ?
C6 C7 C8 C13 0.8(4) . . . . ?
C7 C8 C13 C12 2.3(4) . . . . ?
C7 C8 C13 N1 -174.0(2) . . . . ?
C8 C13 N1 C10 177.2(2) . . . . ?
C10 C1 C2 C3 2.0(3) . . . . ?
C10 C11 C12 C5 -171.0(2) . . . . ?
C10 C11 C12 C13 2.7(3) . . . . ?
C11 C10 N1 C13 1.1(3) . . . . ?
C11 C12 C13 C8 -179.1(2) . . . . ?
C11 C12 C13 N1 -2.0(3) . . . . ?
C12 C5 C6 C7 -0.5(4) . . . . ?
C12 C13 N1 C10 0.6(3) . . . . ?
N1 C10 C11 C4 173.7(2) . . . . ?
N1 C10 C11 C12 -2.3(3) . . . . ?
Se1 C4 C11 C10 -163.64(17) . . . . ?
Se1 C4 C11 C12 11.2(4) . . . . ?
Se2 C5 C6 C7 167.53(19) . . . . ?
Se2 C5 C12 C11 8.0(4) . . . . ?
Se2 C5 C12 C13 -164.98(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.448
_oxdiff_exptl_absorpt_empirical_full_min 0.817
####################################################################### 
# 
# 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_5a
_database_code_depnum_ccdc_archive 'CCDC 2080734'
loop_
_audit_author_name
_audit_author_address
'Louise Male'
;University of Birmingham
United Kingdom
;
_audit_update_record             
;
2021-04-28 deposited with the CCDC.	2021-06-18 downloaded from the CCDC.
;
_audit_creation_date             2021-04-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H27 F4 N Si'
_chemical_formula_sum            'C27 H27 F4 N Si'
_chemical_formula_weight         469.58
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C27 H27 F4 N1 Si1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.2725(4)
_cell_length_b                   19.9141(9)
_cell_length_c                   13.8083(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.265(5)
_cell_angle_gamma                90
_cell_volume                     2230.95(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3957
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.7900
_cell_measurement_theta_min      4.3850
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.359
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.572
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             984
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 7 -5 0.0781
5 -4 -2 0.0876
4 -2 -7 0.0789
-4 2 7 0.0623
3 -5 -8 0.0660
-3 -5 8 0.0534
2 3 -9 0.0592
2 -7 5 0.0833
-3 10 -2 0.0723
5 -4 1 0.0931
5 -5 -2 0.0871
-4 7 3 0.0688
-4 5 5 0.0672
2 -9 -6 0.0751
3 7 -7 0.0799
-1 -11 -4 0.0770
-2 -7 -6 0.1017
1 7 -7 0.0617
-2 -12 0 0.0771
0 5 -8 0.0640
-1 -7 8 0.0612
0 10 -6 0.0656
-2 -12 3 0.0672
3 10 3 0.1184

_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.124
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.5158 7.3005 -5.1463 0.9812 0.0776 0.1768
5.0665 -4.2351 -1.9601 -0.6180 0.7233 -0.3080
4.1541 -1.6895 -6.8052 -0.0786 0.9926 -0.0920
-3.9917 2.2055 6.9882 0.0790 -0.9963 0.0353
3.0228 -4.5885 -7.5462 -0.0771 0.9678 0.2396
-2.5350 -4.9240 7.8221 -0.5124 -0.8368 0.1931
1.7336 2.5894 -8.6996 0.5204 0.8507 0.0741
2.4906 -7.3872 5.1333 -0.9826 -0.0782 -0.1684
-2.8477 10.0148 -2.0884 0.9696 -0.2323 -0.0769
4.8622 -4.0638 0.8976 -0.7695 0.4702 -0.4322
4.8475 -5.4295 -2.3447 -0.6372 0.7448 -0.1982
-4.2862 7.4207 2.9791 0.6499 -0.7600 -0.0089
-4.2032 5.4793 5.3700 0.3830 -0.9231 -0.0333
1.9889 -9.1289 -5.9506 -0.3240 0.7825 0.5317
3.1071 6.7193 -6.5493 0.4727 0.7734 -0.4225
-0.8174 -11.2906 -3.8030 -0.2969 0.3452 0.8903
-2.2531 -7.2293 -5.5483 0.1816 0.2946 0.9382
1.2123 7.2986 -7.3799 0.7479 0.6398 -0.1769
-1.7726 -12.1620 -0.1593 -0.4801 -0.0369 0.8764
0.4797 5.2663 -8.1486 0.7587 0.6487 0.0603
-1.0548 -6.8817 7.5873 -0.7540 -0.6449 0.1249
-0.0042 9.5376 -5.9367 0.9017 0.3745 -0.2159
-1.6953 -11.8079 2.8372 -0.6587 -0.2743 0.7006
2.8396 9.5642 2.7345 0.0664 -0.0331 -0.9972

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8851
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.127
_diffrn_reflns_theta_min         3.948
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00 -17.00   1.00    1.00    --  -42.02 -57.00-120.00   93
  2  ω    -85.00 -12.00   1.00    1.00    --  -42.02 125.00 -30.00   73
  3  ω    -57.00 -15.00   1.00    1.00    --  -42.02 -57.00 120.00   42
  4  ω     21.00  95.00   1.00    1.01    --  104.05 -94.00 -60.00   74
  5  ω    140.00 174.00   1.00    1.01    --  104.05  61.00  30.00   34
  6  ω     51.00 119.00   1.00    1.01    --  104.05 -45.00 -60.00   68
  7  ω    108.00 177.00   1.00    1.01    --  104.05 125.00 -90.00   69
  8  ω    152.00 178.00   1.00    1.01    --  104.05  77.00-120.00   26
  9  ω     21.00 170.00   1.00    1.01    --  104.05   0.00-120.00  149
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1005962000
_diffrn_orient_matrix_UB_12      0.0549692000
_diffrn_orient_matrix_UB_13      -0.0635043000
_diffrn_orient_matrix_UB_21      0.1025131000
_diffrn_orient_matrix_UB_22      -0.0108513000
_diffrn_orient_matrix_UB_23      -0.0805878000
_diffrn_orient_matrix_UB_31      -0.1243557000
_diffrn_orient_matrix_UB_32      -0.0532916000
_diffrn_orient_matrix_UB_33      -0.0491614000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3707
_reflns_number_total             4330
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0510P)²+0.8252P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1036
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C19(H19), C22(H22), C25(H25)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1455(2) 0.69783(8) 0.55473(12) 0.0189(3) Uani 1 1 d . . . . .
H1 H 0.070146 0.732059 0.534098 0.023 Uiso 1 1 calc R U . . .
C2 C 0.1132(2) 0.64716(8) 0.61882(12) 0.0207(3) Uani 1 1 d . . . . .
H2 H 0.013210 0.648912 0.639990 0.025 Uiso 1 1 calc R U . . .
C3 C 0.2193(2) 0.59450(8) 0.65312(12) 0.0192(3) Uani 1 1 d . . . . .
H3 H 0.191077 0.563040 0.696754 0.023 Uiso 1 1 calc R U . . .
C4 C 0.36937(19) 0.58953(8) 0.62094(11) 0.0153(3) Uani 1 1 d . . . . .
C5 C 0.65017(19) 0.59102(8) 0.51615(11) 0.0156(3) Uani 1 1 d . . . . .
C6 C 0.7612(2) 0.59758(8) 0.45207(12) 0.0195(3) Uani 1 1 d . . . . .
H6 H 0.846033 0.566717 0.453709 0.023 Uiso 1 1 calc R U . . .
C7 C 0.7424(2) 0.65119(8) 0.38570(12) 0.0204(3) Uani 1 1 d . . . . .
H7 H 0.816320 0.654337 0.343056 0.025 Uiso 1 1 calc R U . . .
C8 C 0.6198(2) 0.70072(8) 0.37880(12) 0.0192(3) Uani 1 1 d . . . . .
H8 H 0.612267 0.735496 0.333180 0.023 Uiso 1 1 calc R U . . .
C9 C 0.29561(19) 0.69467(8) 0.52325(11) 0.0158(3) Uani 1 1 d . . . . .
C10 C 0.39778(18) 0.64009(8) 0.55651(11) 0.0141(3) Uani 1 1 d . . . . .
C11 C 0.52966(18) 0.64050(7) 0.50748(11) 0.0144(3) Uani 1 1 d . . . . .
C12 C 0.51005(19) 0.69564(8) 0.44295(11) 0.0158(3) Uani 1 1 d . . . . .
C13 C 0.50061(19) 0.53868(8) 0.64171(11) 0.0158(3) Uani 1 1 d . . . . .
C14 C 0.4994(2) 0.48878(8) 0.71278(11) 0.0192(3) Uani 1 1 d . . . . .
C15 C 0.6197(2) 0.44022(8) 0.73397(12) 0.0215(3) Uani 1 1 d . . . . .
C16 C 0.7479(2) 0.43998(8) 0.68365(12) 0.0220(4) Uani 1 1 d . . . . .
C17 C 0.75509(19) 0.48876(8) 0.61428(12) 0.0192(3) Uani 1 1 d . . . . .
C18 C 0.63668(19) 0.53906(8) 0.59027(11) 0.0162(3) Uani 1 1 d . . . . .
C19 C 0.1661(2) 0.80974(8) 0.29309(12) 0.0202(3) Uani 1 1 d . . . . .
H19 H 0.146751 0.854966 0.265268 0.024 Uiso 1 1 calc R U . . .
C20 C -0.0001(2) 0.78164(9) 0.30788(13) 0.0263(4) Uani 1 1 d . . . . .
H20A H 0.015539 0.737295 0.335380 0.039 Uiso 1 1 calc R U . . .
H20B H -0.075102 0.779775 0.245401 0.039 Uiso 1 1 calc R U . . .
H20C H -0.044632 0.810267 0.352094 0.039 Uiso 1 1 calc R U . . .
C21 C 0.2332(2) 0.76633(9) 0.21797(12) 0.0241(4) Uani 1 1 d . . . . .
H21A H 0.333533 0.785668 0.205638 0.036 Uiso 1 1 calc R U . . .
H21B H 0.153333 0.764382 0.157401 0.036 Uiso 1 1 calc R U . . .
H21C H 0.254670 0.721789 0.243900 0.036 Uiso 1 1 calc R U . . .
C22 C 0.2155(2) 0.85967(8) 0.50758(12) 0.0229(4) Uani 1 1 d . . . . .
H22 H 0.126007 0.829766 0.517426 0.027 Uiso 1 1 calc R U . . .
C23 C 0.3262(3) 0.86827(11) 0.60957(14) 0.0365(5) Uani 1 1 d . . . . .
H23A H 0.260828 0.882921 0.655894 0.055 Uiso 1 1 calc R U . . .
H23B H 0.409609 0.901137 0.605798 0.055 Uiso 1 1 calc R U . . .
H23C H 0.377414 0.826144 0.630912 0.055 Uiso 1 1 calc R U . . .
C24 C 0.1330(2) 0.92706(9) 0.47279(14) 0.0286(4) Uani 1 1 d . . . . .
H24A H 0.216316 0.960243 0.470401 0.043 Uiso 1 1 calc R U . . .
H24B H 0.065325 0.941287 0.518088 0.043 Uiso 1 1 calc R U . . .
H24C H 0.065914 0.921693 0.408199 0.043 Uiso 1 1 calc R U . . .
C25 C 0.5105(2) 0.86079(8) 0.39319(12) 0.0208(3) Uani 1 1 d . . . . .
H25 H 0.545445 0.837628 0.338121 0.025 Uiso 1 1 calc R U . . .
C26 C 0.6580(2) 0.85897(10) 0.47999(14) 0.0314(4) Uani 1 1 d . . . . .
H26A H 0.631841 0.883788 0.534504 0.047 Uiso 1 1 calc R U . . .
H26B H 0.752266 0.878727 0.460112 0.047 Uiso 1 1 calc R U . . .
H26C H 0.682245 0.813243 0.499642 0.047 Uiso 1 1 calc R U . . .
C27 C 0.4740(2) 0.93392(9) 0.35999(14) 0.0292(4) Uani 1 1 d . . . . .
H27A H 0.384067 0.934868 0.304305 0.044 Uiso 1 1 calc R U . . .
H27B H 0.570067 0.953238 0.341700 0.044 Uiso 1 1 calc R U . . .
H27C H 0.445131 0.959284 0.413246 0.044 Uiso 1 1 calc R U . . .
F1 F 0.37862(12) 0.48688(5) 0.76523(7) 0.0240(2) Uani 1 1 d . . . . .
F2 F 0.61190(14) 0.39421(5) 0.80385(7) 0.0292(2) Uani 1 1 d . . . . .
F3 F 0.86642(13) 0.39346(5) 0.70401(8) 0.0301(3) Uani 1 1 d . . . . .
F4 F 0.88671(12) 0.48648(5) 0.57036(8) 0.0254(2) Uani 1 1 d . . . . .
N1 N 0.36887(16) 0.73289(7) 0.45607(9) 0.0162(3) Uani 1 1 d . . . . .
Si1 Si 0.31699(5) 0.81699(2) 0.41349(3) 0.01629(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.402(2) . ?
C1 C9 1.395(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.402(2) . ?
C4 C10 1.394(2) . ?
C4 C13 1.471(2) . ?
C5 C6 1.400(2) . ?
C5 C11 1.390(2) . ?
C5 C18 1.475(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.396(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.405(2) . ?
C8 H8 0.9300 . ?
C8 C12 1.390(2) . ?
C9 C10 1.398(2) . ?
C9 N1 1.424(2) . ?
C10 C11 1.392(2) . ?
C11 C12 1.403(2) . ?
C12 N1 1.425(2) . ?
C13 C14 1.398(2) . ?
C13 C18 1.444(2) . ?
C14 C15 1.378(2) . ?
C14 F1 1.3439(19) . ?
C15 C16 1.377(2) . ?
C15 F2 1.3413(19) . ?
C16 C17 1.374(2) . ?
C16 F3 1.3384(19) . ?
C17 C18 1.395(2) . ?
C17 F4 1.3466(19) . ?
C19 H19 0.9800 . ?
C19 C20 1.534(2) . ?
C19 C21 1.535(2) . ?
C19 Si1 1.8794(16) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22 0.9800 . ?
C22 C23 1.532(2) . ?
C22 C24 1.539(2) . ?
C22 Si1 1.8820(17) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25 0.9800 . ?
C25 C26 1.535(2) . ?
C25 C27 1.539(2) . ?
C25 Si1 1.8912(17) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
N1 Si1 1.7990(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 121.5 . . ?
C9 C1 H1 121.5 . . ?
C9 C1 C2 117.09(15) . . ?
C1 C2 H2 117.5 . . ?
C3 C2 C1 124.93(15) . . ?
C3 C2 H2 117.5 . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.00(15) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C13 130.72(14) . . ?
C10 C4 C3 114.94(14) . . ?
C10 C4 C13 114.31(14) . . ?
C6 C5 C18 130.69(15) . . ?
C11 C5 C6 115.28(14) . . ?
C11 C5 C18 114.01(14) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 118.94(15) . . ?
C7 C6 H6 120.5 . . ?
C6 C7 H7 117.7 . . ?
C6 C7 C8 124.58(15) . . ?
C8 C7 H7 117.7 . . ?
C7 C8 H8 121.4 . . ?
C12 C8 C7 117.28(15) . . ?
C12 C8 H8 121.4 . . ?
C1 C9 C10 116.78(14) . . ?
C1 C9 N1 134.20(15) . . ?
C10 C9 N1 108.82(13) . . ?
C4 C10 C9 127.21(14) . . ?
C11 C10 C4 124.10(14) . . ?
C11 C10 C9 108.46(13) . . ?
C5 C11 C10 124.82(14) . . ?
C5 C11 C12 126.97(14) . . ?
C10 C11 C12 108.00(13) . . ?
C8 C12 C11 116.91(14) . . ?
C8 C12 N1 134.15(14) . . ?
C11 C12 N1 108.82(13) . . ?
C14 C13 C4 121.32(14) . . ?
C14 C13 C18 117.55(14) . . ?
C18 C13 C4 121.13(14) . . ?
C15 C14 C13 122.95(16) . . ?
F1 C14 C13 120.42(14) . . ?
F1 C14 C15 116.62(14) . . ?
C16 C15 C14 119.41(15) . . ?
F2 C15 C14 119.87(15) . . ?
F2 C15 C16 120.71(15) . . ?
C17 C16 C15 119.49(15) . . ?
F3 C16 C15 120.10(15) . . ?
F3 C16 C17 120.40(16) . . ?
C16 C17 C18 123.32(15) . . ?
F4 C17 C16 116.06(14) . . ?
F4 C17 C18 120.61(14) . . ?
C13 C18 C5 121.14(14) . . ?
C17 C18 C5 121.59(14) . . ?
C17 C18 C13 117.26(14) . . ?
C20 C19 H19 107.8 . . ?
C20 C19 C21 109.64(14) . . ?
C20 C19 Si1 111.59(11) . . ?
C21 C19 H19 107.8 . . ?
C21 C19 Si1 112.06(11) . . ?
Si1 C19 H19 107.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 H22 105.8 . . ?
C23 C22 C24 109.77(15) . . ?
C23 C22 Si1 114.70(13) . . ?
C24 C22 H22 105.8 . . ?
C24 C22 Si1 114.12(12) . . ?
Si1 C22 H22 105.8 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 H25 106.5 . . ?
C26 C25 C27 109.55(14) . . ?
C26 C25 Si1 116.12(12) . . ?
C27 C25 H25 106.5 . . ?
C27 C25 Si1 110.99(12) . . ?
Si1 C25 H25 106.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C9 N1 C12 105.57(12) . . ?
C9 N1 Si1 127.30(11) . . ?
C12 N1 Si1 126.32(10) . . ?
C19 Si1 C22 109.66(8) . . ?
C19 Si1 C25 109.85(7) . . ?
C22 Si1 C25 113.50(8) . . ?
N1 Si1 C19 107.00(7) . . ?
N1 Si1 C22 107.75(7) . . ?
N1 Si1 C25 108.84(7) . . ?

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
C1 C2 C3 C4 -1.4(3) . . . . ?
C1 C9 C10 C4 -2.7(2) . . . . ?
C1 C9 C10 C11 172.07(14) . . . . ?
C1 C9 N1 C12 -168.92(17) . . . . ?
C1 C9 N1 Si1 20.9(3) . . . . ?
C2 C1 C9 C10 1.7(2) . . . . ?
C2 C1 C9 N1 175.87(16) . . . . ?
C2 C3 C4 C10 0.6(2) . . . . ?
C2 C3 C4 C13 -177.48(15) . . . . ?
C3 C4 C10 C9 1.4(2) . . . . ?
C3 C4 C10 C11 -172.55(14) . . . . ?
C3 C4 C13 C14 -8.8(3) . . . . ?
C3 C4 C13 C18 172.06(15) . . . . ?
C4 C10 C11 C5 -0.1(2) . . . . ?
C4 C10 C11 C12 174.87(14) . . . . ?
C4 C13 C14 C15 179.75(15) . . . . ?
C4 C13 C14 F1 -1.1(2) . . . . ?
C4 C13 C18 C5 0.9(2) . . . . ?
C4 C13 C18 C17 -179.68(14) . . . . ?
C5 C6 C7 C8 0.9(2) . . . . ?
C5 C11 C12 C8 1.8(2) . . . . ?
C5 C11 C12 N1 178.45(14) . . . . ?
C6 C5 C11 C10 173.24(14) . . . . ?
C6 C5 C11 C12 -0.8(2) . . . . ?
C6 C5 C18 C13 -173.54(15) . . . . ?
C6 C5 C18 C17 7.1(3) . . . . ?
C6 C7 C8 C12 0.1(2) . . . . ?
C7 C8 C12 C11 -1.4(2) . . . . ?
C7 C8 C12 N1 -176.92(16) . . . . ?
C8 C12 N1 C9 170.23(17) . . . . ?
C8 C12 N1 Si1 -19.5(3) . . . . ?
C9 C1 C2 C3 0.1(3) . . . . ?
C9 C10 C11 C5 -175.06(14) . . . . ?
C9 C10 C11 C12 -0.07(17) . . . . ?
C9 N1 Si1 C19 -94.85(14) . . . . ?
C9 N1 Si1 C22 23.01(15) . . . . ?
C9 N1 Si1 C25 146.50(13) . . . . ?
C10 C4 C13 C14 173.11(14) . . . . ?
C10 C4 C13 C18 -6.1(2) . . . . ?
C10 C9 N1 C12 5.54(16) . . . . ?
C10 C9 N1 Si1 -164.58(11) . . . . ?
C10 C11 C12 C8 -173.04(14) . . . . ?
C10 C11 C12 N1 3.60(17) . . . . ?
C11 C5 C6 C7 -0.6(2) . . . . ?
C11 C5 C18 C13 4.7(2) . . . . ?
C11 C5 C18 C17 -174.71(14) . . . . ?
C11 C12 N1 C9 -5.59(16) . . . . ?
C11 C12 N1 Si1 164.67(11) . . . . ?
C12 N1 Si1 C19 96.98(13) . . . . ?
C12 N1 Si1 C22 -145.16(13) . . . . ?
C12 N1 Si1 C25 -21.67(14) . . . . ?
C13 C4 C10 C9 179.85(14) . . . . ?
C13 C4 C10 C11 5.9(2) . . . . ?
C13 C14 C15 C16 0.0(2) . . . . ?
C13 C14 C15 F2 179.29(14) . . . . ?
C14 C13 C18 C5 -178.30(14) . . . . ?
C14 C13 C18 C17 1.1(2) . . . . ?
C14 C15 C16 C17 1.0(2) . . . . ?
C14 C15 C16 F3 179.44(14) . . . . ?
C15 C16 C17 C18 -0.9(2) . . . . ?
C15 C16 C17 F4 178.00(14) . . . . ?
C16 C17 C18 C5 179.24(15) . . . . ?
C16 C17 C18 C13 -0.2(2) . . . . ?
C18 C5 C6 C7 177.63(15) . . . . ?
C18 C5 C11 C10 -5.3(2) . . . . ?
C18 C5 C11 C12 -179.32(14) . . . . ?
C18 C13 C14 C15 -1.1(2) . . . . ?
C18 C13 C14 F1 178.07(13) . . . . ?
C20 C19 Si1 C22 -48.24(14) . . . . ?
C20 C19 Si1 C25 -173.64(12) . . . . ?
C20 C19 Si1 N1 68.36(13) . . . . ?
C21 C19 Si1 C22 -171.64(11) . . . . ?
C21 C19 Si1 C25 62.96(13) . . . . ?
C21 C19 Si1 N1 -55.04(13) . . . . ?
C23 C22 Si1 C19 179.68(13) . . . . ?
C23 C22 Si1 C25 -57.05(16) . . . . ?
C23 C22 Si1 N1 63.55(15) . . . . ?
C24 C22 Si1 C19 -52.44(15) . . . . ?
C24 C22 Si1 C25 70.83(15) . . . . ?
C24 C22 Si1 N1 -168.57(12) . . . . ?
C26 C25 Si1 C19 -168.95(13) . . . . ?
C26 C25 Si1 C22 67.88(15) . . . . ?
C26 C25 Si1 N1 -52.10(14) . . . . ?
C27 C25 Si1 C19 65.08(13) . . . . ?
C27 C25 Si1 C22 -58.09(14) . . . . ?
C27 C25 Si1 N1 -178.07(11) . . . . ?
F1 C14 C15 C16 -179.18(14) . . . . ?
F1 C14 C15 F2 0.1(2) . . . . ?
F2 C15 C16 C17 -178.29(14) . . . . ?
F2 C15 C16 F3 0.1(2) . . . . ?
F3 C16 C17 C18 -179.33(14) . . . . ?
F3 C16 C17 F4 -0.4(2) . . . . ?
F4 C17 C18 C5 0.4(2) . . . . ?
F4 C17 C18 C13 -179.05(13) . . . . ?
N1 C9 C10 C4 -178.23(14) . . . . ?
N1 C9 C10 C11 -3.49(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.141
_oxdiff_exptl_absorpt_empirical_full_min 0.916
####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 2080733'
loop_
_audit_author_name
_audit_author_address
'Louise Male'
;University of Birmingham
United Kingdom
;
_audit_update_record             
;
2021-04-28 deposited with the CCDC.	2021-06-18 downloaded from the CCDC.
;
_audit_creation_date             2021-04-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H33 N O2 Si'
_chemical_formula_sum            'C23 H33 N O2 Si'
_chemical_formula_weight         383.59
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H33 N1 O2 Si1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_H-M_alt        'P 61'
_space_group_name_Hall           'P 61'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'-x, -y, z+1/2'
'y, -x+y, z+5/6'
'x-y, x, z+1/6'

_cell_length_a                   19.2612(6)
_cell_length_b                   19.2612(6)
_cell_length_c                   9.9892(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3209.4(3)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    6527
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.0440
_cell_measurement_theta_min      4.5130
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.092
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.737
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-12 3 1 0.0482
-12 6 -2 0.0737
7 -12 0 0.0443
-3 12 0 0.0410
-4 -8 0 0.0361
3 5 -5 0.0892
4 8 0 0.0393
-10 -1 -3 0.0726
12 -7 -1 0.0445
10 -5 4 0.0945
4 -4 -6 0.1017
12 -10 0 0.0443
-12 10 1 0.0415
10 -12 -1 0.0413
-10 12 0 0.0394
-7 12 0 0.0410
2 -2 6 0.1074
3 -12 0 0.0427
0 0 6 0.1065
-4 -8 0 0.0411
4 8 0 0.0410
-8 -4 0 0.0377
8 4 0 0.0393
10 1 0 0.0426

_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.075
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-11.9060 3.2762 1.1418 -0.2296 -0.9599 -0.1610
-11.6337 6.1135 -2.3645 0.0731 -0.9284 0.3644
6.8165 -12.4859 0.0990 -0.8527 0.5217 0.0279
-3.2507 12.0633 -0.3864 0.9725 -0.2328 0.0092
-4.4617 -7.8640 0.3831 -0.9236 -0.3832 -0.0092
3.0542 5.0341 -4.9031 0.6388 0.2641 0.7226
4.4617 7.8640 -0.3831 0.9236 0.3832 0.0092
-9.5143 -0.8376 -2.5467 -0.4731 -0.7740 0.4208
12.3891 -6.8141 -0.7679 -0.0784 0.9898 0.1194
9.8321 -4.9973 4.0038 -0.0629 0.7839 -0.6176
4.0214 -3.8888 -6.0368 -0.1317 0.3203 0.9381
11.6600 -9.7175 -0.1873 -0.3828 0.9227 0.0460
-11.5062 9.6599 0.9710 0.3777 -0.9108 -0.1668
9.6412 -11.6362 -0.6253 -0.6445 0.7539 0.1280
-9.7099 11.6721 0.1220 0.6490 -0.7591 -0.0505
-6.8209 12.4790 -0.2221 0.8529 -0.5220 -0.0089
1.5309 -2.2156 6.3762 -0.1903 0.1150 -0.9750
3.2381 -12.0739 -0.2280 -0.9689 0.2321 0.0855
0.0411 0.4706 6.4787 -0.0089 0.0008 -1.0000
-4.4457 -7.8911 -0.2514 -0.9201 -0.3816 0.0886
4.4575 7.8892 -0.0072 0.9226 0.3827 -0.0488
-7.8515 -4.4914 0.2159 -0.7600 -0.6499 0.0089
7.8515 4.4914 -0.2159 0.7600 0.6499 -0.0089
10.4665 0.6462 -0.3876 0.5217 0.8526 0.0295

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            18641
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.043
_diffrn_reflns_theta_min         4.591
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  33.00   1.00    4.21    --  -41.77  38.00-150.00   96
  2  ω     58.00  84.00   1.00    4.21    --   41.77-127.00 -35.00   26
  3  ω    -64.00 -10.00   1.00    4.21    --  -42.27 -26.00  -0.62   54
  4  ω      9.00  34.00   1.00    4.21    --   42.27  80.00  46.55   25
  5  ω     14.00  41.00   1.00    4.21    --   42.27  57.00  30.00   27
  6  ω     73.00  99.00   1.00    5.00    --  102.47  63.00  15.07   26
  7  ω     72.00  98.00   1.00    5.00    --  102.47  66.00  35.01   26
  8  ω     72.00  98.00   1.00    5.00    --  102.47  71.00  34.83   26
  9  ω    138.00 164.00   1.00    5.00    --  102.47  57.00  78.35   26
 10  ω     72.00  98.00   1.00    5.00    --  102.47  71.00 -63.63   26
 11  ω     73.00  99.00   1.00    5.00    --  102.47  62.00   3.66   26
 12  ω    110.00 146.00   1.00    5.00    --  102.47 125.00 120.00   36
 13  ω     29.00 112.00   1.00    5.00    --  102.47-125.00 -60.00   83
 14  ω     73.00  99.00   1.00    5.00    --  102.47  61.00  30.00   26
 15  ω     73.00  99.00   1.00    5.00    --  102.47  61.00   0.00   26
 16  ω     71.00  96.00   1.00    5.00    --  102.47  72.00   3.13   25
 17  ω     74.00 100.00   1.00    5.00    --  102.47  57.00  78.35   26
 18  ω     79.00 104.00   1.00    5.00    --  102.47  45.00  30.00   25
 19  ω     80.00 175.00   1.00    5.00    --  102.47  49.00 -22.22   95
 20  ω     73.00  99.00   1.00    5.00    --  102.47  61.00 -30.00   26
 21  ω     77.00 103.00   1.00    5.00    --  102.47  56.00  -6.09   26
 22  ω   -114.00 -30.00   1.00    4.21    --  -42.27 -57.00 120.00   84
 23  ω   -114.00 -14.00   1.00    4.21    --  -42.27 -57.00-150.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0438452000
_diffrn_orient_matrix_UB_12      0.0921639000
_diffrn_orient_matrix_UB_13      -0.0083468000
_diffrn_orient_matrix_UB_21      0.0812790000
_diffrn_orient_matrix_UB_22      0.0025856000
_diffrn_orient_matrix_UB_23      -0.0005801000
_diffrn_orient_matrix_UB_31      -0.0025834000
_diffrn_orient_matrix_UB_32      -0.0048660000
_diffrn_orient_matrix_UB_33      -0.1539824000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_full    0.896
_reflns_Friedel_fraction_max     0.876
_reflns_number_gt                3457
_reflns_number_total             3827
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.249
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 
;
 Flack x determined using 1387 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3827
_refine_ls_number_restraints     50
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0611
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1152P)²+1.8207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1663
_refine_ls_wR_factor_ref         0.1764
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O2-C14
 1.42 with sigma of 0.02
 O1-C13
 1.42 with sigma of 0.02
 C13-C4
 1.51 with sigma of 0.02
 O1A-C13A
 1.42 with sigma of 0.02
 C13A-C4
 1.51 with sigma of 0.02
 O1-C4
 2.37 with sigma of 0.04
 O1A-C4
 2.37 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C4 \\sim C13 \\sim O1: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
C4 \\sim C13A \\sim O1A: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 C4, C13, O1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C4, C13A, O1A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C13A)=Sof(H13C)=Sof(H13D)=Sof(O1A)=Sof(H1AA)=1-FVAR(1)
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(O1)=Sof(H1A)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C15(H15), C18(H18), C21(H21)
6.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C13A(H13C,H13D), C14(H14A,H14B)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C7(H7), C8(H8)
6.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
6.e Idealised tetrahedral OH refined as rotating group:
 O1(H1A), O1A(H1AA), O2(H2A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6654(4) 1.0095(3) 0.7221(7) 0.0596(17) Uani 1 1 d . . . . .
H1 H 0.617619 0.988928 0.769627 0.072 Uiso 1 1 calc R U . . .
C2 C 0.7382(5) 1.0641(3) 0.7798(8) 0.064(2) Uani 1 1 d . . . . .
H2 H 0.739163 1.081586 0.866914 0.077 Uiso 1 1 calc R U . . .
C3 C 0.8094(4) 1.0928(3) 0.7093(9) 0.066(2) Uani 1 1 d . . . . .
H3 H 0.857280 1.128315 0.751477 0.079 Uiso 1 1 calc R U . . .
C4 C 0.8117(3) 1.0706(3) 0.5785(8) 0.0578(18) Uani 1 1 d D U . . .
C5 C 0.7518(3) 0.9955(3) 0.2562(8) 0.0532(15) Uani 1 1 d . . . . .
C6 C 0.7097(4) 0.9456(3) 0.1502(7) 0.0512(14) Uani 1 1 d . . . . .
H6 H 0.734472 0.954071 0.067145 0.061 Uiso 1 1 calc R U . . .
C7 C 0.6315(4) 0.8835(4) 0.1650(7) 0.0471(13) Uani 1 1 d . . . . .
H7 H 0.605771 0.848430 0.094320 0.056 Uiso 1 1 calc R U . . .
C8 C 0.5920(3) 0.8736(3) 0.2837(6) 0.0396(12) Uani 1 1 d . . . . .
H8 H 0.538886 0.833141 0.292772 0.047 Uiso 1 1 calc R U . . .
C9 C 0.6669(3) 0.9867(3) 0.5897(6) 0.0422(12) Uani 1 1 d . . . . .
C10 C 0.7376(3) 1.0190(3) 0.5133(6) 0.0418(12) Uani 1 1 d . . . . .
C11 C 0.7144(3) 0.9829(3) 0.3809(6) 0.0381(12) Uani 1 1 d . . . . .
C12 C 0.6318(3) 0.9244(3) 0.3907(5) 0.0349(11) Uani 1 1 d . . . . .
C13 C 0.8917(9) 1.0850(12) 0.528(3) 0.097(7) Uani 0.59(2) 1 d D U P A 1
H13A H 0.884573 1.041314 0.470039 0.116 Uiso 0.59(2) 1 calc R U P A 1
H13B H 0.918763 1.134616 0.477205 0.116 Uiso 0.59(2) 1 calc R U P A 1
C13A C 0.8925(13) 1.1066(15) 0.515(3) 0.063(6) Uani 0.41(2) 1 d D U P A 2
H13C H 0.886631 1.116121 0.421749 0.076 Uiso 0.41(2) 1 calc R U P A 2
H13D H 0.926077 1.158488 0.556464 0.076 Uiso 0.41(2) 1 calc R U P A 2
C14 C 0.8353(4) 1.0635(4) 0.2239(11) 0.087(3) Uani 1 1 d D . . . .
H14A H 0.835356 1.085735 0.136742 0.104 Uiso 1 1 calc R U . . .
H14B H 0.851708 1.105659 0.290056 0.104 Uiso 1 1 calc R U . . .
C15 C 0.5192(3) 0.8159(3) 0.7285(6) 0.0422(12) Uani 1 1 d . . . . .
H15 H 0.573194 0.852597 0.762313 0.051 Uiso 1 1 calc R U . . .
C16 C 0.4646(4) 0.7956(3) 0.8504(6) 0.0551(16) Uani 1 1 d . . . . .
H16A H 0.409633 0.765518 0.822423 0.083 Uiso 1 1 calc R U . . .
H16B H 0.474123 0.844292 0.893014 0.083 Uiso 1 1 calc R U . . .
H16C H 0.475756 0.764348 0.912316 0.083 Uiso 1 1 calc R U . . .
C17 C 0.5233(4) 0.7434(3) 0.6750(6) 0.0449(13) Uani 1 1 d . . . . .
H17A H 0.542232 0.722503 0.744321 0.067 Uiso 1 1 calc R U . . .
H17B H 0.559365 0.759620 0.600168 0.067 Uiso 1 1 calc R U . . .
H17C H 0.470855 0.702675 0.646917 0.067 Uiso 1 1 calc R U . . .
C18 C 0.4757(3) 0.9495(3) 0.6513(5) 0.0385(11) Uani 1 1 d . . . . .
H18 H 0.505921 0.971909 0.734226 0.046 Uiso 1 1 calc R U . . .
C19 C 0.5028(4) 1.0201(3) 0.5541(6) 0.0452(13) Uani 1 1 d . . . . .
H19A H 0.474493 1.001157 0.470991 0.068 Uiso 1 1 calc R U . . .
H19B H 0.559399 1.044133 0.538264 0.068 Uiso 1 1 calc R U . . .
H19C H 0.491637 1.059199 0.592278 0.068 Uiso 1 1 calc R U . . .
C20 C 0.3872(4) 0.9151(3) 0.6870(6) 0.0494(14) Uani 1 1 d . . . . .
H20A H 0.380197 0.955303 0.731601 0.074 Uiso 1 1 calc R U . . .
H20B H 0.370273 0.869713 0.745170 0.074 Uiso 1 1 calc R U . . .
H20C H 0.355551 0.898525 0.606751 0.074 Uiso 1 1 calc R U . . .
C21 C 0.4270(3) 0.8026(2) 0.4646(5) 0.0299(10) Uani 1 1 d . . . . .
H21 H 0.449331 0.771490 0.424717 0.036 Uiso 1 1 calc R U . . .
C22 C 0.4106(3) 0.8446(3) 0.3493(5) 0.0355(10) Uani 1 1 d . . . . .
H22A H 0.387432 0.808115 0.275595 0.053 Uiso 1 1 calc R U . . .
H22B H 0.460052 0.890356 0.321203 0.053 Uiso 1 1 calc R U . . .
H22C H 0.374164 0.861835 0.378529 0.053 Uiso 1 1 calc R U . . .
C23 C 0.3475(3) 0.7420(3) 0.5314(6) 0.0392(11) Uani 1 1 d . . . . .
H23A H 0.323761 0.770102 0.572837 0.059 Uiso 1 1 calc R U . . .
H23B H 0.357533 0.712169 0.598055 0.059 Uiso 1 1 calc R U . . .
H23C H 0.311613 0.705866 0.464947 0.059 Uiso 1 1 calc R U . . .
N1 N 0.6011(2) 0.9281(2) 0.5163(5) 0.0368(9) Uani 1 1 d . . . . .
O1 O 0.9378(4) 1.0895(5) 0.6453(16) 0.091(5) Uani 0.59(2) 1 d D U P A 1
H1A H 0.976772 1.085758 0.622936 0.136 Uiso 0.59(2) 1 calc R U P A 1
O1A O 0.9336(14) 1.0645(12) 0.521(4) 0.152(14) Uani 0.41(2) 1 d D U P A 2
H1AA H 0.970918 1.083872 0.467352 0.228 Uiso 0.41(2) 1 calc R U P A 2
O2 O 0.8902(3) 1.0338(3) 0.2238(13) 0.145(4) Uani 1 1 d D . . . .
H2A H 0.871149 0.992080 0.267110 0.218 Uiso 1 1 calc R U . . .
Si1 Si 0.50318(7) 0.87294(7) 0.58959(14) 0.0312(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.388(9) . ?
C1 C9 1.398(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(12) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(11) . ?
C4 C10 1.425(8) . ?
C4 C13 1.512(18) . ?
C4 C13A 1.49(2) . ?
C5 C6 1.387(10) . ?
C5 C11 1.398(9) . ?
C5 C14 1.517(8) . ?
C6 H6 0.9300 . ?
C6 C7 1.386(9) . ?
C7 H7 0.9300 . ?
C7 C8 1.369(8) . ?
C8 H8 0.9300 . ?
C8 C12 1.393(7) . ?
C9 C10 1.406(8) . ?
C9 N1 1.409(6) . ?
C10 C11 1.456(8) . ?
C11 C12 1.421(6) . ?
C12 N1 1.403(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 O1 1.45(2) . ?
C13A H13C 0.9700 . ?
C13A H13D 0.9700 . ?
C13A O1A 1.39(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 O2 1.431(10) . ?
C15 H15 0.9800 . ?
C15 C16 1.526(8) . ?
C15 C17 1.534(7) . ?
C15 Si1 1.888(6) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18 0.9800 . ?
C18 C19 1.534(7) . ?
C18 C20 1.531(8) . ?
C18 Si1 1.901(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21 0.9800 . ?
C21 C22 1.529(7) . ?
C21 C23 1.538(6) . ?
C21 Si1 1.886(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
N1 Si1 1.794(4) . ?
O1 H1A 0.8200 . ?
O1A H1AA 0.8200 . ?
O2 H2A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 121.3 . . ?
C2 C1 C9 117.3(7) . . ?
C9 C1 H1 121.3 . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 120.9(7) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 118.9 . . ?
C4 C3 C2 122.3(5) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 C10 118.2(6) . . ?
C3 C4 C13 116.7(11) . . ?
C3 C4 C13A 116.3(13) . . ?
C10 C4 C13 123.2(11) . . ?
C10 C4 C13A 125.4(13) . . ?
C6 C5 C11 119.3(5) . . ?
C6 C5 C14 115.8(7) . . ?
C11 C5 C14 124.8(7) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.5(6) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.0(6) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C12 119.7(5) . . ?
C12 C8 H8 120.2 . . ?
C1 C9 C10 122.8(5) . . ?
C1 C9 N1 126.3(6) . . ?
C10 C9 N1 110.8(5) . . ?
C4 C10 C11 135.1(6) . . ?
C9 C10 C4 118.1(6) . . ?
C9 C10 C11 106.5(4) . . ?
C5 C11 C10 135.9(5) . . ?
C5 C11 C12 118.3(5) . . ?
C12 C11 C10 105.6(5) . . ?
C8 C12 C11 120.6(5) . . ?
C8 C12 N1 128.6(4) . . ?
N1 C12 C11 110.8(4) . . ?
C4 C13 H13A 110.5 . . ?
C4 C13 H13B 110.5 . . ?
H13A C13 H13B 108.7 . . ?
O1 C13 C4 106.0(15) . . ?
O1 C13 H13A 110.5 . . ?
O1 C13 H13B 110.5 . . ?
C4 C13A H13C 107.6 . . ?
C4 C13A H13D 107.6 . . ?
H13C C13A H13D 107.1 . . ?
O1A C13A C4 118.7(19) . . ?
O1A C13A H13C 107.6 . . ?
O1A C13A H13D 107.6 . . ?
C5 C14 H14A 109.8 . . ?
C5 C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
O2 C14 C5 109.4(5) . . ?
O2 C14 H14A 109.8 . . ?
O2 C14 H14B 109.8 . . ?
C16 C15 H15 104.9 . . ?
C16 C15 C17 112.8(5) . . ?
C16 C15 Si1 116.3(4) . . ?
C17 C15 H15 104.9 . . ?
C17 C15 Si1 111.8(4) . . ?
Si1 C15 H15 104.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 H18 106.3 . . ?
C19 C18 Si1 112.3(4) . . ?
C20 C18 H18 106.3 . . ?
C20 C18 C19 110.1(5) . . ?
C20 C18 Si1 114.9(3) . . ?
Si1 C18 H18 106.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 H21 106.7 . . ?
C22 C21 C23 109.8(4) . . ?
C22 C21 Si1 114.2(3) . . ?
C23 C21 H21 106.7 . . ?
C23 C21 Si1 112.3(3) . . ?
Si1 C21 H21 106.7 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C9 N1 Si1 121.3(4) . . ?
C12 N1 C9 105.8(4) . . ?
C12 N1 Si1 132.8(3) . . ?
C13 O1 H1A 109.5 . . ?
C13A O1A H1AA 109.5 . . ?
C14 O2 H2A 109.5 . . ?
C15 Si1 C18 113.8(2) . . ?
C21 Si1 C15 111.3(2) . . ?
C21 Si1 C18 110.7(2) . . ?
N1 Si1 C15 102.4(2) . . ?
N1 Si1 C18 106.9(2) . . ?
N1 Si1 C21 111.4(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1A O1 0.82 2.38 3.041(7) 138.6 5_564 yes
O1A H1AA O1A 0.82 1.93 2.745(11) 175.1 5_564 yes
O2 H2A O2 0.82 2.21 3.008(5) 163.6 6_655 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
C1 C2 C3 C4 1.6(9) . . . . ?
C1 C9 C10 C4 6.7(8) . . . . ?
C1 C9 C10 C11 -178.0(5) . . . . ?
C1 C9 N1 C12 -178.2(5) . . . . ?
C1 C9 N1 Si1 -0.5(7) . . . . ?
C2 C1 C9 C10 -2.5(8) . . . . ?
C2 C1 C9 N1 175.0(5) . . . . ?
C2 C3 C4 C10 2.7(8) . . . . ?
C2 C3 C4 C13 -162.0(10) . . . . ?
C2 C3 C4 C13A 179.8(11) . . . . ?
C3 C4 C10 C9 -6.6(7) . . . . ?
C3 C4 C10 C11 179.8(5) . . . . ?
C3 C4 C13 O1 22.1(16) . . . . ?
C3 C4 C13A O1A 93(3) . . . . ?
C4 C10 C11 C5 -15.9(10) . . . . ?
C4 C10 C11 C12 168.0(6) . . . . ?
C5 C6 C7 C8 4.7(9) . . . . ?
C5 C11 C12 C8 8.6(7) . . . . ?
C5 C11 C12 N1 -170.9(4) . . . . ?
C6 C5 C11 C10 178.0(5) . . . . ?
C6 C5 C11 C12 -6.3(7) . . . . ?
C6 C5 C14 O2 -81.3(11) . . . . ?
C6 C7 C8 C12 -2.4(8) . . . . ?
C7 C8 C12 C11 -4.3(8) . . . . ?
C7 C8 C12 N1 175.1(5) . . . . ?
C8 C12 N1 C9 177.0(5) . . . . ?
C8 C12 N1 Si1 -0.4(8) . . . . ?
C9 C1 C2 C3 -1.7(9) . . . . ?
C9 C10 C11 C5 170.1(6) . . . . ?
C9 C10 C11 C12 -6.1(5) . . . . ?
C9 N1 Si1 C15 -63.6(4) . . . . ?
C9 N1 Si1 C18 56.3(4) . . . . ?
C9 N1 Si1 C21 177.3(4) . . . . ?
C10 C4 C13 O1 -141.7(10) . . . . ?
C10 C4 C13A O1A -90(3) . . . . ?
C10 C9 N1 C12 -0.5(6) . . . . ?
C10 C9 N1 Si1 177.3(3) . . . . ?
C10 C11 C12 C8 -174.5(4) . . . . ?
C10 C11 C12 N1 6.0(5) . . . . ?
C11 C5 C6 C7 -0.2(8) . . . . ?
C11 C5 C14 O2 102.0(9) . . . . ?
C11 C12 N1 C9 -3.6(5) . . . . ?
C11 C12 N1 Si1 179.0(4) . . . . ?
C12 N1 Si1 C15 113.5(5) . . . . ?
C12 N1 Si1 C18 -126.6(5) . . . . ?
C12 N1 Si1 C21 -5.6(5) . . . . ?
C13 C4 C10 C9 157.0(10) . . . . ?
C13 C4 C10 C11 -16.6(13) . . . . ?
C13A C4 C10 C9 176.6(12) . . . . ?
C13A C4 C10 C11 3.1(14) . . . . ?
C14 C5 C6 C7 -177.1(6) . . . . ?
C14 C5 C11 C10 -5.4(10) . . . . ?
C14 C5 C11 C12 170.3(6) . . . . ?
C16 C15 Si1 C18 36.3(5) . . . . ?
C16 C15 Si1 C21 -89.6(4) . . . . ?
C16 C15 Si1 N1 151.2(4) . . . . ?
C17 C15 Si1 C18 167.8(4) . . . . ?
C17 C15 Si1 C21 41.9(4) . . . . ?
C17 C15 Si1 N1 -77.2(4) . . . . ?
C22 C21 Si1 C15 179.7(3) . . . . ?
C22 C21 Si1 C18 52.2(4) . . . . ?
C22 C21 Si1 N1 -66.6(4) . . . . ?
C23 C21 Si1 C15 53.9(4) . . . . ?
C23 C21 Si1 C18 -73.7(4) . . . . ?
C23 C21 Si1 N1 167.5(3) . . . . ?
N1 C9 C10 C4 -171.1(4) . . . . ?
N1 C9 C10 C11 4.1(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.359
_oxdiff_exptl_absorpt_empirical_full_min 0.823
####################################################################### 
# 
# 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_8a
_database_code_depnum_ccdc_archive 'CCDC 2079910'
loop_
_audit_author_name
_audit_author_address
'Louise Male'
;University of Birmingham
United Kingdom
;
_audit_update_record             
;
2021-04-25 deposited with the CCDC.	2021-06-18 downloaded from the CCDC.
;
_audit_creation_date             2019-08-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H33 N Si2'
_chemical_formula_sum            'C23 H33 N Si2'
_chemical_formula_weight         379.68
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H33 N1 Si2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.1260(5)
_cell_length_b                   15.4832(4)
_cell_length_c                   12.3174(5)
_cell_angle_alpha                90
_cell_angle_beta                 117.891(5)
_cell_angle_gamma                90
_cell_volume                     2212.51(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5523
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.2700
_cell_measurement_theta_min      4.7260
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.483
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -5 7 0.0684
0 1 7 0.0599
3 5 5 0.0778
-8 1 1 0.0682
4 -8 -3 0.0708
-6 -4 -2 0.0844
8 1 0 0.0888
0 9 4 0.0905
1 -8 3 0.0755
4 0 4 0.0657
2 10 0 0.1011
1 -2 6 0.0539
3 8 -4 0.0998
-1 6 6 0.0679
-8 -3 4 0.0844
-6 6 5 0.0874
2 8 4 0.0805
-8 -2 1 0.0737
-6 1 -2 0.0567
-6 4 -1 0.0711
-1 6 -5 0.0750
-4 -2 -5 0.0840
5 -3 -7 0.0750
-4 -7 -2 0.0912
4 1 -8 0.0772
6 6 -6 0.0847
5 -6 -6 0.0699
8 2 -2 0.0948

_exptl_crystal_size_max          0.208
_exptl_crystal_size_mid          0.173
_exptl_crystal_size_min          0.137
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3.0004 -5.0001 6.9999 0.9326 -0.3843 -0.0001
0.4999 0.9999 6.9999 0.6818 -0.2981 -0.7087
2.5001 5.0000 5.0000 0.3185 -0.1175 -0.9808
-8.0002 1.0000 0.9999 0.3178 0.7827 0.5531
4.4999 -8.0000 -3.0000 -0.2486 -0.8470 0.3930
-5.5002 -4.0000 -2.0000 0.0558 0.3345 0.9223
7.5002 1.0000 0.0000 -0.2485 -0.6417 -0.7278
-0.4998 9.0000 4.0000 0.2077 0.4916 -0.8977
1.4997 -8.0001 2.9999 0.4591 -0.8371 0.1449
4.5000 -0.0000 4.0000 0.2776 -0.6099 -0.7383
2.0004 10.0001 0.0001 -0.3034 0.5072 -0.8430
0.9998 -2.0001 5.9999 0.6369 -0.5088 -0.4673
2.5004 8.0001 -3.9999 -0.6817 0.5035 -0.4121
-1.0000 6.0000 6.0000 0.5018 0.2384 -0.8244
-8.0004 -3.0001 3.9999 0.7243 0.3667 0.5635
-5.5001 6.0000 4.9999 0.5333 0.7110 -0.3423
1.5002 8.0000 4.0000 0.1723 0.2322 -1.0073
-8.0003 -2.0001 0.9999 0.3909 0.5737 0.7531
-6.0001 1.0000 -2.0000 -0.0511 0.7303 0.6330
-6.0000 4.0000 -1.0000 -0.0211 0.8936 0.3476
-0.9997 6.0001 -4.9999 -0.6314 0.7418 0.1152
-3.5000 -2.0000 -5.0000 -0.3617 0.4214 0.8689
4.5002 -2.9999 -6.9999 -0.7825 -0.3155 0.4013
-4.0003 -7.0000 -2.0000 0.0841 -0.0169 0.9901
3.5003 1.0001 -7.9999 -0.9531 0.1039 0.3082
6.0005 6.0001 -5.9999 -0.9436 0.1236 -0.4164
5.0001 -6.0000 -5.9999 -0.6213 -0.6178 0.4718
8.0003 2.0001 -1.9999 -0.4939 -0.5279 -0.6677

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8569
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.131
_diffrn_reflns_theta_min         4.763
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -112.00 -16.00   1.00    1.00    --  -42.56 -57.00 -30.00   96
  2  ω    -63.00  28.00   1.00    1.00    --  -42.56  57.00 120.00   91
  3  ω     90.00 115.00   1.00    1.00    --   42.56  38.00   0.00   25
  4  ω     22.00  49.00   1.00    1.00    --   42.56  38.00   0.00   27
  5  ω     80.00 166.00   1.00    1.53    --  106.63  77.00-180.00   86
  6  ω     96.00 129.00   1.00    1.53    --  106.63 125.00  90.00   33
  7  ω     36.00 127.00   1.00    1.53    --  106.63 -45.00-180.00   91
  8  ω     35.00 131.00   1.00    1.53    --  106.63 -45.00  30.00   96
  9  ω     74.00 171.00   1.00    1.53    --  106.63   0.00 120.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0298882000
_diffrn_orient_matrix_UB_12      -0.0243650000
_diffrn_orient_matrix_UB_13      0.1030169000
_diffrn_orient_matrix_UB_21      -0.0948478000
_diffrn_orient_matrix_UB_22      0.0696916000
_diffrn_orient_matrix_UB_23      -0.0457695000
_diffrn_orient_matrix_UB_31      -0.0881410000
_diffrn_orient_matrix_UB_32      -0.0666712000
_diffrn_orient_matrix_UB_33      -0.0854213000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3612
_reflns_number_total             4107
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         4107
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0361
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0534P)²+0.8633P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1018
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C17(H17), C20(H20)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,
 H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.48636(14) 0.73789(10) 0.43291(15) 0.0235(3) Uani 1 1 d . . . . .
H1 H 0.559437 0.746341 0.498498 0.028 Uiso 1 1 calc R . . . .
C2 C 0.39261(15) 0.78857(10) 0.41878(15) 0.0250(4) Uani 1 1 d . . . . .
H2 H 0.405624 0.830745 0.477607 0.030 Uiso 1 1 calc R . . . .
C3 C 0.27997(14) 0.77998(10) 0.32155(15) 0.0229(3) Uani 1 1 d . . . . .
H3 H 0.221457 0.815961 0.317248 0.028 Uiso 1 1 calc R . . . .
C4 C 0.25656(13) 0.71721(10) 0.23166(15) 0.0202(3) Uani 1 1 d . . . . .
C5 C 0.24253(13) 0.58546(10) 0.06616(14) 0.0192(3) Uani 1 1 d . . . . .
C6 C 0.25118(14) 0.51921(10) -0.00613(15) 0.0217(3) Uani 1 1 d . . . . .
H6 H 0.186706 0.501535 -0.077249 0.026 Uiso 1 1 calc R . . . .
C7 C 0.35887(14) 0.47956(10) 0.03017(15) 0.0222(3) Uani 1 1 d . . . . .
H7 H 0.362541 0.435668 -0.019420 0.027 Uiso 1 1 calc R . . . .
C8 C 0.46090(13) 0.50133(10) 0.13545(15) 0.0199(3) Uani 1 1 d . . . . .
H8 H 0.529752 0.472833 0.155222 0.024 Uiso 1 1 calc R . . . .
C10 C 0.46592(13) 0.67375(9) 0.34423(14) 0.0184(3) Uani 1 1 d . . . . .
C11 C 0.35335(13) 0.66920(9) 0.25125(14) 0.0178(3) Uani 1 1 d . . . . .
C12 C 0.34659(13) 0.60404(9) 0.16869(14) 0.0169(3) Uani 1 1 d . . . . .
C13 C 0.45519(13) 0.56760(9) 0.20969(14) 0.0164(3) Uani 1 1 d . . . . .
C14 C 0.76490(14) 0.67790(10) 0.37540(15) 0.0211(3) Uani 1 1 d . . . . .
H14 H 0.846921 0.670753 0.433075 0.025 Uiso 1 1 calc R . . . .
C15 C 0.75157(16) 0.66601(11) 0.24579(15) 0.0283(4) Uani 1 1 d . . . . .
H15A H 0.671697 0.670976 0.186591 0.042 Uiso 1 1 calc GR . . . .
H15B H 0.779528 0.609961 0.239301 0.042 Uiso 1 1 calc GR . . . .
H15C H 0.795147 0.709647 0.230349 0.042 Uiso 1 1 calc GR . . . .
C16 C 0.73202(17) 0.77045(11) 0.39103(18) 0.0310(4) Uani 1 1 d . . . . .
H16A H 0.779090 0.810614 0.375003 0.047 Uiso 1 1 calc GR . . . .
H16B H 0.744049 0.778228 0.473517 0.047 Uiso 1 1 calc GR . . . .
H16C H 0.652355 0.780400 0.334360 0.047 Uiso 1 1 calc GR . . . .
C17 C 0.72125(13) 0.60559(10) 0.58087(14) 0.0203(3) Uani 1 1 d . . . . .
H17 H 0.707606 0.666481 0.591560 0.024 Uiso 1 1 calc R . . . .
C18 C 0.84900(16) 0.58883(15) 0.66750(17) 0.0389(5) Uani 1 1 d . . . . .
H18A H 0.865292 0.601408 0.750383 0.058 Uiso 1 1 calc GR . . . .
H18B H 0.895243 0.625196 0.644863 0.058 Uiso 1 1 calc GR . . . .
H18C H 0.866575 0.529377 0.661587 0.058 Uiso 1 1 calc GR . . . .
C19 C 0.64570(18) 0.55336(13) 0.62084(17) 0.0349(4) Uani 1 1 d . . . . .
H19A H 0.659609 0.492850 0.616987 0.052 Uiso 1 1 calc GR . . . .
H19B H 0.566017 0.565838 0.567119 0.052 Uiso 1 1 calc GR . . . .
H19C H 0.664028 0.568608 0.703526 0.052 Uiso 1 1 calc GR . . . .
C20 C 0.72081(13) 0.48313(10) 0.37426(15) 0.0207(3) Uani 1 1 d . . . . .
H20 H 0.690306 0.482899 0.284856 0.025 Uiso 1 1 calc R . . . .
C21 C 0.85112(14) 0.46774(12) 0.42860(17) 0.0301(4) Uani 1 1 d . . . . .
H21A H 0.883821 0.459102 0.515671 0.045 Uiso 1 1 calc GR . . . .
H21B H 0.886429 0.517042 0.412626 0.045 Uiso 1 1 calc GR . . . .
H21C H 0.864545 0.417461 0.391480 0.045 Uiso 1 1 calc GR . . . .
C22 C 0.66217(16) 0.40747(10) 0.40359(17) 0.0266(4) Uani 1 1 d . . . . .
H22A H 0.672992 0.355483 0.367748 0.040 Uiso 1 1 calc GR . . . .
H22B H 0.581236 0.419091 0.370349 0.040 Uiso 1 1 calc GR . . . .
H22C H 0.695595 0.400509 0.491007 0.040 Uiso 1 1 calc GR . . . .
C23 C 0.07698(14) 0.74360(11) -0.05022(16) 0.0264(4) Uani 1 1 d . . . . .
H23A H 0.031470 0.786096 -0.035700 0.040 Uiso 1 1 calc GR . . . .
H23B H 0.029099 0.712352 -0.124064 0.040 Uiso 1 1 calc GR . . . .
H23C H 0.137927 0.771743 -0.058917 0.040 Uiso 1 1 calc GR . . . .
C24 C 0.02213(15) 0.61534(12) 0.10319(19) 0.0334(4) Uani 1 1 d . . . . .
H24A H 0.054630 0.573816 0.168504 0.050 Uiso 1 1 calc GR . . . .
H24B H -0.030364 0.586865 0.028559 0.050 Uiso 1 1 calc GR . . . .
H24C H -0.018452 0.658706 0.123477 0.050 Uiso 1 1 calc GR . . . .
N1 N 0.53333(11) 0.60963(8) 0.32226(12) 0.0173(3) Uani 1 1 d . . . . .
Si1 Si 0.68447(3) 0.59262(3) 0.41413(4) 0.01622(12) Uani 1 1 d . . . . .
Si2 Si 0.13993(3) 0.66715(3) 0.08183(4) 0.02071(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.400(2) . ?
C1 C10 1.406(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.408(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.395(2) . ?
C4 C11 1.392(2) . ?
C4 Si2 1.9254(17) . ?
C5 C6 1.397(2) . ?
C5 C12 1.389(2) . ?
C5 Si2 1.9219(16) . ?
C6 H6 0.9300 . ?
C6 C7 1.408(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.401(2) . ?
C8 H8 0.9300 . ?
C8 C13 1.400(2) . ?
C10 C11 1.384(2) . ?
C10 N1 1.4374(19) . ?
C11 C12 1.406(2) . ?
C12 C13 1.390(2) . ?
C13 N1 1.4378(19) . ?
C14 H14 0.9800 . ?
C14 C15 1.534(2) . ?
C14 C16 1.534(2) . ?
C14 Si1 1.8860(16) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17 0.9800 . ?
C17 C18 1.531(2) . ?
C17 C19 1.529(2) . ?
C17 Si1 1.8878(16) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20 0.9800 . ?
C20 C21 1.536(2) . ?
C20 C22 1.535(2) . ?
C20 Si1 1.8873(16) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C23 Si2 1.8634(17) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C24 Si2 1.8665(18) . ?
N1 Si1 1.7847(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 121.2 . . ?
C2 C1 C10 117.52(15) . . ?
C10 C1 H1 121.2 . . ?
C1 C2 H2 117.8 . . ?
C1 C2 C3 124.42(15) . . ?
C3 C2 H2 117.8 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.65(15) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 Si2 145.32(13) . . ?
C11 C4 C3 112.96(14) . . ?
C11 C4 Si2 101.72(11) . . ?
C6 C5 Si2 144.76(12) . . ?
C12 C5 C6 113.13(14) . . ?
C12 C5 Si2 102.10(11) . . ?
C5 C6 H6 120.5 . . ?
C5 C6 C7 119.10(14) . . ?
C7 C6 H6 120.5 . . ?
C6 C7 H7 117.6 . . ?
C8 C7 C6 124.87(15) . . ?
C8 C7 H7 117.6 . . ?
C7 C8 H8 121.3 . . ?
C13 C8 C7 117.44(14) . . ?
C13 C8 H8 121.3 . . ?
C1 C10 N1 136.35(14) . . ?
C11 C10 C1 114.87(14) . . ?
C11 C10 N1 108.78(13) . . ?
C4 C11 C12 120.95(14) . . ?
C10 C11 C4 130.58(15) . . ?
C10 C11 C12 108.47(13) . . ?
C5 C12 C11 120.59(14) . . ?
C5 C12 C13 130.65(14) . . ?
C13 C12 C11 108.76(13) . . ?
C8 C13 N1 136.87(14) . . ?
C12 C13 C8 114.80(14) . . ?
C12 C13 N1 108.32(13) . . ?
C15 C14 H14 107.0 . . ?
C15 C14 C16 109.93(14) . . ?
C15 C14 Si1 111.99(11) . . ?
C16 C14 H14 107.0 . . ?
C16 C14 Si1 113.49(11) . . ?
Si1 C14 H14 107.0 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 H17 106.2 . . ?
C18 C17 Si1 112.31(12) . . ?
C19 C17 H17 106.2 . . ?
C19 C17 C18 110.48(15) . . ?
C19 C17 Si1 114.83(11) . . ?
Si1 C17 H17 106.2 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 H20 106.0 . . ?
C21 C20 Si1 113.04(11) . . ?
C22 C20 H20 106.0 . . ?
C22 C20 C21 110.97(14) . . ?
C22 C20 Si1 114.12(11) . . ?
Si1 C20 H20 106.0 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
Si2 C23 H23A 109.5 . . ?
Si2 C23 H23B 109.5 . . ?
Si2 C23 H23C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
Si2 C24 H24A 109.5 . . ?
Si2 C24 H24B 109.5 . . ?
Si2 C24 H24C 109.5 . . ?
C10 N1 C13 105.66(12) . . ?
C10 N1 Si1 125.60(10) . . ?
C13 N1 Si1 128.65(10) . . ?
C14 Si1 C17 108.19(7) . . ?
C14 Si1 C20 108.88(7) . . ?
C20 Si1 C17 114.30(7) . . ?
N1 Si1 C14 108.91(7) . . ?
N1 Si1 C17 108.47(7) . . ?
N1 Si1 C20 107.99(6) . . ?
C5 Si2 C4 94.64(7) . . ?
C23 Si2 C4 114.21(7) . . ?
C23 Si2 C5 112.08(7) . . ?
C23 Si2 C24 109.73(8) . . ?
C24 Si2 C4 112.18(8) . . ?
C24 Si2 C5 113.39(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.3(3) . . . . ?
C1 C10 C11 C4 -0.7(2) . . . . ?
C1 C10 C11 C12 178.69(14) . . . . ?
C1 C10 N1 C13 -178.03(18) . . . . ?
C1 C10 N1 Si1 -1.2(3) . . . . ?
C2 C1 C10 C11 0.6(2) . . . . ?
C2 C1 C10 N1 179.69(16) . . . . ?
C2 C3 C4 C11 -0.3(2) . . . . ?
C2 C3 C4 Si2 -179.01(16) . . . . ?
C3 C4 C11 C10 0.5(2) . . . . ?
C3 C4 C11 C12 -178.83(14) . . . . ?
C4 C11 C12 C5 -0.7(2) . . . . ?
C4 C11 C12 C13 179.38(14) . . . . ?
C5 C6 C7 C8 0.1(2) . . . . ?
C5 C12 C13 C8 0.1(2) . . . . ?
C5 C12 C13 N1 -179.13(15) . . . . ?
C6 C5 C12 C11 179.86(14) . . . . ?
C6 C5 C12 C13 -0.3(2) . . . . ?
C6 C7 C8 C13 -0.2(2) . . . . ?
C7 C8 C13 C12 0.1(2) . . . . ?
C7 C8 C13 N1 179.06(16) . . . . ?
C8 C13 N1 C10 179.90(17) . . . . ?
C8 C13 N1 Si1 3.2(3) . . . . ?
C10 C1 C2 C3 -0.5(3) . . . . ?
C10 C11 C12 C5 179.81(14) . . . . ?
C10 C11 C12 C13 -0.10(17) . . . . ?
C10 N1 Si1 C14 -78.15(13) . . . . ?
C10 N1 Si1 C17 39.38(14) . . . . ?
C10 N1 Si1 C20 163.76(12) . . . . ?
C11 C10 N1 C13 1.05(16) . . . . ?
C11 C10 N1 Si1 177.87(11) . . . . ?
C11 C12 C13 C8 -179.99(13) . . . . ?
C11 C12 C13 N1 0.77(17) . . . . ?
C12 C5 C6 C7 0.1(2) . . . . ?
C12 C13 N1 C10 -1.11(16) . . . . ?
C12 C13 N1 Si1 -177.79(11) . . . . ?
C13 N1 Si1 C14 97.92(14) . . . . ?
C13 N1 Si1 C17 -144.55(13) . . . . ?
C13 N1 Si1 C20 -20.17(15) . . . . ?
C15 C14 Si1 C17 173.36(11) . . . . ?
C15 C14 Si1 C20 48.59(13) . . . . ?
C15 C14 Si1 N1 -68.93(13) . . . . ?
C16 C14 Si1 C17 -61.45(14) . . . . ?
C16 C14 Si1 C20 173.79(12) . . . . ?
C16 C14 Si1 N1 56.26(13) . . . . ?
C18 C17 Si1 C14 -64.11(14) . . . . ?
C18 C17 Si1 C20 57.36(14) . . . . ?
C18 C17 Si1 N1 177.90(12) . . . . ?
C19 C17 Si1 C14 168.54(13) . . . . ?
C19 C17 Si1 C20 -69.98(15) . . . . ?
C19 C17 Si1 N1 50.55(14) . . . . ?
C21 C20 Si1 C14 50.93(14) . . . . ?
C21 C20 Si1 C17 -70.16(14) . . . . ?
C21 C20 Si1 N1 169.03(12) . . . . ?
C22 C20 Si1 C14 179.00(12) . . . . ?
C22 C20 Si1 C17 57.91(14) . . . . ?
C22 C20 Si1 N1 -62.90(13) . . . . ?
N1 C10 C11 C4 179.98(15) . . . . ?
N1 C10 C11 C12 -0.61(17) . . . . ?
Si2 C4 C11 C10 179.79(15) . . . . ?
Si2 C4 C11 C12 0.44(17) . . . . ?
Si2 C5 C6 C7 179.05(15) . . . . ?
Si2 C5 C12 C11 0.51(17) . . . . ?
Si2 C5 C12 C13 -179.60(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.203
_oxdiff_exptl_absorpt_empirical_full_min 0.878
####################################################################### 
# 
# 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_6b
_database_code_depnum_ccdc_archive 'CCDC 2080735'
loop_
_audit_author_name
_audit_author_address
'Louise Male'
;University of Birmingham
United Kingdom
;
_audit_update_record             
;
2021-04-28 deposited with the CCDC.	2021-06-18 downloaded from the CCDC.
;
_audit_creation_date             2021-04-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H7 Cl2 N'
_chemical_formula_sum            'C12 H7 Cl2 N'
_chemical_formula_weight         236.09
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H27 Cl2 N1 Si1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   3.8267(2)
_cell_length_b                   14.2898(6)
_cell_length_c                   17.5522(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     959.80(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4133
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.8170
_cell_measurement_theta_min      3.8780
_shelx_estimated_absorpt_T_max   0.763
_shelx_estimated_absorpt_T_min   0.387
_exptl_absorpt_coefficient_mu    5.725
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light brown'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 9 2 0.0485
0 -9 4 0.0410
0 7 -7 0.0346
-1 2 -11 0.0368
2 4 -1 0.0923
0 -1 -11 0.0213
0 1 11 0.0216
1 1 10 0.0403
0 4 10 0.0279
0 -4 -10 0.0246
-1 6 8 0.0380
0 -6 -9 0.0295
2 5 3 0.0824
0 -9 1 0.0395
2 -7 4 0.0582
-2 5 -6 0.0577
0 -5 10 0.0279
0 2 -11 0.0229
0 -2 11 0.0219
0 1 11 0.0295
0 -8 -6 0.0345
0 8 6 0.0377
0 -2 11 0.0216
-1 1 0 0.0919
-2 -4 -1 0.1021
0 9 3 0.0331

_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.05
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.8325 8.5127 2.4121 0.7756 -0.5947 -0.2113
0.1611 -8.5284 4.4144 -0.2845 0.9582 -0.0310
0.0528 7.0596 -7.3847 -0.0254 -0.9960 0.0858
-0.8652 1.5679 -10.5043 -0.5668 -0.7389 -0.3645
2.2293 4.0065 -1.0617 0.0995 -0.3313 0.9383
0.1096 -0.7499 -11.3440 -0.8237 -0.5669 -0.0091
0.2666 0.9148 11.2704 0.8131 0.5593 0.1611
1.0043 1.1796 10.3190 0.7337 0.5043 0.4554
-0.0482 3.6084 10.4933 0.9565 0.2839 0.0679
0.1933 -3.5491 -10.4880 -0.9586 -0.2846 -0.0092
-0.5729 5.8104 8.4811 0.9924 -0.0252 -0.1202
0.2561 -6.0017 -8.6049 -0.9996 0.0256 -0.0092
1.9595 4.9843 3.4044 0.4800 -0.1709 0.8604
0.4742 -9.0665 1.0075 -0.5655 0.8215 0.0740
1.5014 -6.6249 4.0156 -0.2426 0.8143 0.5274
-1.5125 5.1577 -6.4415 -0.0203 -0.8280 -0.5603
0.0431 -4.8042 9.7428 0.3332 0.9428 -0.0090
0.0571 2.1412 -11.0824 -0.6083 -0.7937 0.0089
0.4982 -1.8395 10.9296 0.5936 0.7752 0.2161
-0.1540 0.7301 11.3361 0.8238 0.5669 -0.0089
0.4528 -7.7815 -5.8385 -0.9413 0.3328 0.0564
-0.3363 7.8469 5.8721 0.9428 -0.3332 -0.0089
0.3622 -1.9189 11.0212 0.6005 0.7832 0.1611
-0.9981 0.9970 -0.0016 0.1117 -0.1099 -0.3852
-2.2408 -3.8766 -1.2554 -0.2471 0.1911 -0.9500
0.0726 9.0217 2.6193 0.7837 -0.6009 0.1574

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9168
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.841
_diffrn_reflns_theta_min         3.989
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -67.00  32.00   1.00    1.00    --  -42.02  38.00 -60.00   99
  2  ω    -70.00  31.00   1.00    1.00    --  -42.02  57.00  30.00  101
  3  ω     28.00 137.00   1.00    2.26    --  104.05 -77.00-120.00  109
  4  ω     28.00 132.00   1.00    2.26    --  104.05 -30.00 -90.00  104
  5  ω     28.00 132.00   1.00    2.26    --  104.05 -30.00-180.00  104
  6  ω     97.00 177.00   1.00    2.26    --  104.05 125.00 -60.00   80
  7  ω     30.00 110.00   1.00    2.26    --  104.05-120.00  87.00   80
  8  ω   -116.00 -17.00   1.00    1.00    --  -42.02 -38.00 -90.00   99
  9  ω   -114.00 -14.00   1.00    1.00    --  -42.02 -57.00  30.00  100
 10  ω    103.00 178.00   1.00    2.26    --  104.05  77.00-120.00   75
 11  ω     51.00 178.00   1.00    2.26    --  104.05  15.00-150.00  127
 12  ω     51.00 178.00   1.00    2.26    --  104.05  15.00 120.00  127
 13  ω     76.00 178.00   1.00    2.26    --  104.05  30.00   0.00  102
 14  ω   -114.00 -14.00   1.00    1.00    --  -42.02 -57.00-120.00  100
 15  ω   -114.00 -14.00   1.00    1.00    --  -42.02 -57.00 150.00  100
 16  ω     75.00 100.00   1.00    2.26    --  104.05  61.00 -90.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0445517000
_diffrn_orient_matrix_UB_12      0.0675672000
_diffrn_orient_matrix_UB_13      0.0677139000
_diffrn_orient_matrix_UB_21      0.0270952000
_diffrn_orient_matrix_UB_22      -0.0829995000
_diffrn_orient_matrix_UB_23      0.0557220000
_diffrn_orient_matrix_UB_31      0.3990997000
_diffrn_orient_matrix_UB_32      0.0131338000
_diffrn_orient_matrix_UB_33      0.0037890000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.628
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                1785
_reflns_number_total             1895
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 674 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.045(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1895
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0270
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0318P)²+0.4595P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0664
_refine_ls_wR_factor_ref         0.0683
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C7(H7), C8(H8)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2214(9) 0.45811(19) 0.39615(15) 0.0198(6) Uani 1 1 d . . . . .
H1 H 0.151196 0.516703 0.413407 0.024 Uiso 1 1 calc R U . . .
C2 C 0.3673(9) 0.3935(2) 0.44474(15) 0.0219(6) Uani 1 1 d . . . . .
H2 H 0.392526 0.408019 0.496103 0.026 Uiso 1 1 calc R U . . .
C3 C 0.4779(8) 0.30656(19) 0.41794(16) 0.0202(6) Uani 1 1 d . . . . .
H3 H 0.578417 0.264094 0.451591 0.024 Uiso 1 1 calc R U . . .
C4 C 0.4403(8) 0.28249(18) 0.34191(16) 0.0179(6) Uani 1 1 d . . . . .
C5 C 0.1949(8) 0.28681(18) 0.14464(15) 0.0165(6) Uani 1 1 d . . . . .
C6 C 0.0659(8) 0.31587(19) 0.07498(15) 0.0187(6) Uani 1 1 d . . . . .
H6 H 0.075419 0.275403 0.033535 0.022 Uiso 1 1 calc R U . . .
C7 C -0.0783(9) 0.4049(2) 0.06575(16) 0.0205(6) Uani 1 1 d . . . . .
H7 H -0.164219 0.422821 0.018387 0.025 Uiso 1 1 calc R U . . .
C8 C -0.0947(9) 0.46636(19) 0.12587(15) 0.0191(6) Uani 1 1 d . . . . .
H8 H -0.189632 0.525867 0.120216 0.023 Uiso 1 1 calc R U . . .
C9 C 0.1826(8) 0.43223(18) 0.31974(15) 0.0173(6) Uani 1 1 d . . . . .
C10 C 0.2853(8) 0.34378(17) 0.28991(15) 0.0157(6) Uani 1 1 d . . . . .
C11 C 0.1875(7) 0.34575(17) 0.20862(15) 0.0148(6) Uani 1 1 d . . . . .
C12 C 0.0370(8) 0.43581(19) 0.19586(15) 0.0165(6) Uani 1 1 d . . . . .
Cl1 Cl 0.60414(19) 0.17297(4) 0.31709(4) 0.02082(17) Uani 1 1 d . . . . .
Cl2 Cl 0.36177(19) 0.17322(4) 0.14536(4) 0.02005(17) Uani 1 1 d . . . . .
N1 N 0.0415(7) 0.48585(17) 0.26285(12) 0.0169(5) Uani 1 1 d . . . . .
H1A H -0.072(14) 0.543(3) 0.269(2) 0.058(14) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.375(4) . ?
C1 C9 1.399(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.395(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(4) . ?
C4 C10 1.397(4) . ?
C4 Cl1 1.741(3) . ?
C5 C6 1.382(4) . ?
C5 C11 1.404(4) . ?
C5 Cl2 1.744(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.396(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.374(4) . ?
C8 H8 0.9300 . ?
C8 C12 1.398(4) . ?
C9 C10 1.423(4) . ?
C9 N1 1.370(4) . ?
C10 C11 1.475(4) . ?
C11 C12 1.428(4) . ?
C12 N1 1.376(3) . ?
N1 H1A 0.94(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 121.3 . . ?
C2 C1 C9 117.4(3) . . ?
C9 C1 H1 121.3 . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.8(2) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C10 121.2(3) . . ?
C3 C4 Cl1 115.3(2) . . ?
C10 C4 Cl1 123.6(2) . . ?
C6 C5 C11 121.3(2) . . ?
C6 C5 Cl2 114.6(2) . . ?
C11 C5 Cl2 124.0(2) . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.2(2) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.7(3) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 121.3 . . ?
C7 C8 C12 117.3(3) . . ?
C12 C8 H8 121.3 . . ?
C1 C9 C10 123.9(3) . . ?
N1 C9 C1 126.4(3) . . ?
N1 C9 C10 109.7(2) . . ?
C4 C10 C9 115.7(2) . . ?
C4 C10 C11 138.7(2) . . ?
C9 C10 C11 105.6(2) . . ?
C5 C11 C10 139.2(2) . . ?
C5 C11 C12 115.1(2) . . ?
C12 C11 C10 105.7(2) . . ?
C8 C12 C11 124.4(2) . . ?
N1 C12 C8 126.4(3) . . ?
N1 C12 C11 109.2(2) . . ?
C9 N1 C12 109.7(2) . . ?
C9 N1 H1A 126(3) . . ?
C12 N1 H1A 124(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A Cl2 0.94(5) 2.63(5) 3.485(2) 152(3) 3 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
C1 C2 C3 C4 -0.7(5) . . . . ?
C1 C9 C10 C4 -1.6(5) . . . . ?
C1 C9 C10 C11 178.3(3) . . . . ?
C1 C9 N1 C12 -178.1(3) . . . . ?
C2 C1 C9 C10 -0.1(5) . . . . ?
C2 C1 C9 N1 179.4(3) . . . . ?
C2 C3 C4 C10 -1.1(5) . . . . ?
C2 C3 C4 Cl1 178.0(2) . . . . ?
C3 C4 C10 C9 2.1(4) . . . . ?
C3 C4 C10 C11 -177.7(3) . . . . ?
C4 C10 C11 C5 1.9(7) . . . . ?
C4 C10 C11 C12 -179.6(4) . . . . ?
C5 C6 C7 C8 0.2(5) . . . . ?
C5 C11 C12 C8 -0.4(4) . . . . ?
C5 C11 C12 N1 179.2(2) . . . . ?
C6 C5 C11 C10 178.8(3) . . . . ?
C6 C5 C11 C12 0.4(4) . . . . ?
C6 C7 C8 C12 -0.2(5) . . . . ?
C7 C8 C12 C11 0.3(5) . . . . ?
C7 C8 C12 N1 -179.2(3) . . . . ?
C8 C12 N1 C9 178.5(3) . . . . ?
C9 C1 C2 C3 1.3(5) . . . . ?
C9 C10 C11 C5 -177.9(4) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C10 C9 N1 C12 1.5(3) . . . . ?
C10 C11 C12 C8 -179.3(3) . . . . ?
C10 C11 C12 N1 0.3(3) . . . . ?
C11 C5 C6 C7 -0.3(5) . . . . ?
C11 C12 N1 C9 -1.1(3) . . . . ?
Cl1 C4 C10 C9 -176.9(2) . . . . ?
Cl1 C4 C10 C11 3.3(5) . . . . ?
Cl2 C5 C6 C7 179.6(2) . . . . ?
Cl2 C5 C11 C10 -1.1(5) . . . . ?
Cl2 C5 C11 C12 -179.5(2) . . . . ?
N1 C9 C10 C4 178.8(3) . . . . ?
N1 C9 C10 C11 -1.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.943
_oxdiff_exptl_absorpt_empirical_full_min 0.749
####################################################################### 
# 
# 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_20a
_database_code_depnum_ccdc_archive 'CCDC 2080736'
loop_
_audit_author_name
_audit_author_address
'Louise Male'
;University of Birmingham
United Kingdom
;
_audit_update_record             
;
2021-06-01 deposited with the CCDC.	2021-06-18 downloaded from the CCDC.
;
_audit_creation_date             2021-04-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H31 N O Si'
_chemical_formula_sum            'C23 H31 N O Si'
_chemical_formula_weight         365.58
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H31 N1 O1 Si1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.0996(3)
_cell_length_b                   14.8381(5)
_cell_length_c                   29.5722(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3992.9(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4113
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.9430
_cell_measurement_theta_min      4.8090
_shelx_estimated_absorpt_T_max   0.902
_shelx_estimated_absorpt_T_min   0.800
_exptl_absorpt_coefficient_mu    1.109
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.846
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light brown'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 3 9 0.0705
-1 -7 13 0.0873
2 8 -8 0.0925
0 4 18 0.0521
2 -3 -17 0.0477
-6 0 2 0.0816
5 -3 9 0.0542
4 -4 13 0.0509
-4 -1 -13 0.0682
-4 3 -13 0.0606
4 1 13 0.0720
2 8 8 0.0912
1 -1 19 0.0493
-1 1 19 0.0480
-3 -2 16 0.0747
2 -2 -17 0.0466
-2 3 17 0.0503
4 5 -8 0.0928
-3 4 14 0.0545
-5 -4 5 0.0905
5 -2 -9 0.0542
-3 6 -12 0.0588
0 8 -11 0.0800
0 -3 -18 0.0457
-2 3 -17 0.0574
4 -6 -4 0.0363
-4 7 4 0.0470
0 -9 -3 0.0923
6 3 -1 0.0814
6 -2 -2 0.0521
1 -8 -11 0.0580
-2 -3 -17 0.0573

_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.095
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5.0033 2.7010 8.6668 0.9725 -0.2328 -0.0089
-0.9368 -6.8473 13.1677 0.4042 0.6619 -0.6313
1.6181 8.4608 -7.5322 -0.2622 -0.4305 0.8637
0.1002 3.8252 17.6005 0.6670 0.5696 0.4803
1.9640 -3.1897 -16.9398 -0.8859 -0.3672 -0.2835
-5.8770 -0.0983 1.9672 0.7916 -0.4838 -0.3733
4.8624 -3.2913 8.7237 -0.3828 0.9224 0.0514
3.5108 -3.9871 13.2503 -0.0788 0.9942 -0.0734
-4.2977 -0.9753 -13.0259 0.0713 -0.8908 -0.4488
-3.6646 3.4267 -13.4297 0.0791 -0.9968 0.0090
4.3096 1.4473 12.8054 -0.0695 0.8671 0.4932
2.3173 7.8773 8.0487 0.1627 0.2685 0.9494
0.7330 -1.1177 18.9181 0.5210 0.8516 0.0576
-0.8098 0.6507 18.9665 0.7537 0.6447 0.1278
-3.2132 -1.7162 15.7442 0.8891 0.3685 -0.2717
2.2943 -2.1767 -17.1407 -0.9106 -0.3781 -0.1670
-1.8552 3.4807 16.8411 0.8757 0.3638 0.3176
4.4901 4.6365 -8.3893 -0.7333 -0.0572 0.6775
-3.3147 4.0880 13.6296 0.9620 0.0767 0.2622
-5.1827 -3.9314 4.8546 0.7160 -0.1723 -0.6765
5.1272 -2.1601 -8.5074 -0.9702 0.2324 0.0694
-2.5532 6.4728 -11.5602 0.0735 -0.9211 0.3822
-0.0944 7.9983 -10.7103 -0.1677 -0.7039 0.6903
0.2093 -2.8018 -18.3424 -0.7071 -0.6041 -0.3675
-2.2756 2.5359 -16.9857 -0.2328 -0.9725 -0.0091
4.4165 -6.1381 -3.5799 -0.8064 0.4941 -0.3249
-3.6106 7.3878 3.7284 0.7400 -0.4537 0.4966
-0.3203 -9.4866 -3.1004 -0.2798 0.1728 -0.9444
5.6125 2.9731 -0.9046 -0.6579 0.4015 0.6371
5.7856 -1.5055 -2.4786 -0.8339 0.5099 0.2113
1.0639 -7.7868 -10.7286 -0.6695 -0.0521 -0.7410
-2.1603 -2.9298 -16.8751 -0.3672 -0.7697 -0.5223

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9832
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.037
_diffrn_reflns_theta_min         5.709
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -14.00   1.00    2.88    --  -42.02 -57.00 -90.00  100
  2  ω     23.00 104.00   1.00   11.54    --  104.05 -94.00  60.00   81
  3  ω     53.00 169.00   1.00   11.54    --  104.05  15.00-150.00  116
  4  ω     21.00 103.00   1.00   11.54    --  104.05 -94.00 -30.00   82
  5  ω    -62.00 -27.00   1.00    2.88    --  -42.27  77.00-180.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1238015000
_diffrn_orient_matrix_UB_12      0.0226658000
_diffrn_orient_matrix_UB_13      0.0336754000
_diffrn_orient_matrix_UB_21      0.0960382000
_diffrn_orient_matrix_UB_22      -0.0342898000
_diffrn_orient_matrix_UB_23      0.0392682000
_diffrn_orient_matrix_UB_31      0.0639980000
_diffrn_orient_matrix_UB_32      0.0953626000
_diffrn_orient_matrix_UB_33      0.0061991000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3383
_reflns_number_total             3879
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3879
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0659P)²+1.3972P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1159
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15), C18(H18), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C7(H7), C8(H8)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5239(2) 0.18343(12) 0.60381(6) 0.0336(4) Uani 1 1 d . . . . .
H1 H 0.519984 0.205634 0.574422 0.040 Uiso 1 1 calc R U . . .
C2 C 0.6121(2) 0.11060(13) 0.61433(6) 0.0348(4) Uani 1 1 d . . . . .
H2 H 0.668563 0.084618 0.591576 0.042 Uiso 1 1 calc R U . . .
C3 C 0.61955(18) 0.07471(11) 0.65775(6) 0.0287(3) Uani 1 1 d . . . . .
H3 H 0.677317 0.024210 0.663312 0.034 Uiso 1 1 calc R U . . .
C4 C 0.54114(16) 0.11402(10) 0.69269(5) 0.0224(3) Uani 1 1 d . . . . .
C5 C 0.34258(15) 0.24606(10) 0.75776(5) 0.0201(3) Uani 1 1 d . . . . .
C6 C 0.25071(17) 0.31119(10) 0.77577(5) 0.0229(3) Uani 1 1 d . . . . .
H6 H 0.232614 0.312070 0.806721 0.028 Uiso 1 1 calc R U . . .
C7 C 0.18490(17) 0.37564(10) 0.74788(5) 0.0243(3) Uani 1 1 d . . . . .
H7 H 0.124552 0.419201 0.760783 0.029 Uiso 1 1 calc R U . . .
C8 C 0.20712(17) 0.37643(10) 0.70144(5) 0.0236(3) Uani 1 1 d . . . . .
H8 H 0.162396 0.419652 0.683292 0.028 Uiso 1 1 calc R U . . .
C9 C 0.44083(16) 0.22303(10) 0.63813(5) 0.0236(3) Uani 1 1 d . . . . .
C10 C 0.45320(15) 0.18880(10) 0.68271(5) 0.0203(3) Uani 1 1 d . . . . .
C11 C 0.36422(15) 0.24552(9) 0.71090(5) 0.0193(3) Uani 1 1 d . . . . .
C12 C 0.29852(15) 0.31055(10) 0.68265(5) 0.0205(3) Uani 1 1 d . . . . .
C13 C 0.55593(16) 0.07738(10) 0.74008(5) 0.0240(3) Uani 1 1 d . . . . .
H13A H 0.575744 0.013241 0.738337 0.029 Uiso 1 1 calc R U . . .
H13B H 0.639866 0.105744 0.754446 0.029 Uiso 1 1 calc R U . . .
C14 C 0.42154(17) 0.17894(10) 0.78727(5) 0.0228(3) Uani 1 1 d . . . . .
H14A H 0.520382 0.200595 0.793000 0.027 Uiso 1 1 calc R U . . .
H14B H 0.371178 0.174956 0.816115 0.027 Uiso 1 1 calc R U . . .
C15 C 0.3943(2) 0.47641(13) 0.59456(7) 0.0403(4) Uani 1 1 d . . . . .
H15 H 0.376538 0.508746 0.566188 0.048 Uiso 1 1 calc R U . . .
C16 C 0.5595(3) 0.4550(2) 0.59592(12) 0.0716(9) Uani 1 1 d . . . . .
H16A H 0.614496 0.510253 0.596064 0.107 Uiso 1 1 calc R U . . .
H16B H 0.585791 0.420218 0.569770 0.107 Uiso 1 1 calc R U . . .
H16C H 0.581550 0.421244 0.622763 0.107 Uiso 1 1 calc R U . . .
C17 C 0.3512(3) 0.54053(14) 0.63270(7) 0.0584(7) Uani 1 1 d . . . . .
H17A H 0.375392 0.513714 0.661286 0.088 Uiso 1 1 calc R U . . .
H17B H 0.247456 0.551944 0.631411 0.088 Uiso 1 1 calc R U . . .
H17C H 0.403703 0.596264 0.629368 0.088 Uiso 1 1 calc R U . . .
C18 C 0.3374(2) 0.31277(14) 0.53524(6) 0.0365(4) Uani 1 1 d . . . . .
H18 H 0.440116 0.293913 0.538235 0.044 Uiso 1 1 calc R U . . .
C19 C 0.2506(3) 0.22719(16) 0.52509(7) 0.0505(5) Uani 1 1 d . . . . .
H19A H 0.149079 0.242199 0.520416 0.076 Uiso 1 1 calc R U . . .
H19B H 0.258883 0.186320 0.550123 0.076 Uiso 1 1 calc R U . . .
H19C H 0.289121 0.199188 0.498335 0.076 Uiso 1 1 calc R U . . .
C20 C 0.3330(3) 0.37804(19) 0.49462(7) 0.0566(6) Uani 1 1 d . . . . .
H20A H 0.369948 0.348049 0.468202 0.085 Uiso 1 1 calc R U . . .
H20B H 0.392708 0.429803 0.501043 0.085 Uiso 1 1 calc R U . . .
H20C H 0.233488 0.396862 0.489349 0.085 Uiso 1 1 calc R U . . .
C21 C 0.08289(17) 0.38926(12) 0.59478(5) 0.0273(3) Uani 1 1 d . . . . .
H21 H 0.068787 0.434531 0.618516 0.033 Uiso 1 1 calc R U . . .
C22 C -0.00862(19) 0.30693(13) 0.60849(6) 0.0378(4) Uani 1 1 d . . . . .
H22A H -0.110332 0.323676 0.610437 0.057 Uiso 1 1 calc R U . . .
H22B H 0.024194 0.285248 0.637362 0.057 Uiso 1 1 calc R U . . .
H22C H 0.002960 0.260320 0.586263 0.057 Uiso 1 1 calc R U . . .
C23 C 0.0205(2) 0.43005(13) 0.55092(6) 0.0342(4) Uani 1 1 d . . . . .
H23A H 0.029434 0.387067 0.526816 0.051 Uiso 1 1 calc R U . . .
H23B H 0.074420 0.483579 0.543356 0.051 Uiso 1 1 calc R U . . .
H23C H -0.081180 0.444925 0.555258 0.051 Uiso 1 1 calc R U . . .
N1 N 0.34224(14) 0.29678(9) 0.63716(4) 0.0231(3) Uani 1 1 d . . . . .
O1 O 0.42977(12) 0.09111(7) 0.76778(4) 0.0236(2) Uani 1 1 d . . . . .
Si1 Si 0.28723(4) 0.36801(3) 0.59100(2) 0.02275(14) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.382(2) . ?
C1 C9 1.395(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.392(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(2) . ?
C4 C10 1.400(2) . ?
C4 C13 1.509(2) . ?
C5 C6 1.384(2) . ?
C5 C11 1.399(2) . ?
C5 C14 1.507(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.398(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.388(2) . ?
C8 H8 0.9300 . ?
C8 C12 1.399(2) . ?
C9 C10 1.417(2) . ?
C9 N1 1.4153(19) . ?
C10 C11 1.435(2) . ?
C11 C12 1.410(2) . ?
C12 N1 1.4174(19) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 O1 1.4249(18) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 O1 1.4270(18) . ?
C15 H15 0.9800 . ?
C15 C16 1.537(3) . ?
C15 C17 1.527(3) . ?
C15 Si1 1.8835(19) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18 0.9800 . ?
C18 C19 1.525(3) . ?
C18 C20 1.544(3) . ?
C18 Si1 1.8972(18) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21 0.9800 . ?
C21 C22 1.533(2) . ?
C21 C23 1.540(2) . ?
C21 Si1 1.8892(17) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
N1 Si1 1.7976(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 120.6 . . ?
C2 C1 C9 118.71(15) . . ?
C9 C1 H1 120.6 . . ?
C1 C2 H2 118.8 . . ?
C1 C2 C3 122.35(15) . . ?
C3 C2 H2 118.8 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.16(15) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C10 118.12(14) . . ?
C3 C4 C13 119.69(14) . . ?
C10 C4 C13 122.17(14) . . ?
C6 C5 C11 118.03(13) . . ?
C6 C5 C14 121.77(13) . . ?
C11 C5 C14 120.18(13) . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.61(14) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.82(14) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 H8 120.9 . . ?
C7 C8 C12 118.28(14) . . ?
C12 C8 H8 120.9 . . ?
C1 C9 C10 118.86(14) . . ?
C1 C9 N1 130.87(14) . . ?
N1 C9 C10 110.25(13) . . ?
C4 C10 C9 121.72(14) . . ?
C4 C10 C11 131.69(14) . . ?
C9 C10 C11 106.59(13) . . ?
C5 C11 C10 131.15(14) . . ?
C5 C11 C12 121.56(13) . . ?
C12 C11 C10 107.24(13) . . ?
C8 C12 C11 119.68(13) . . ?
C8 C12 N1 130.14(14) . . ?
C11 C12 N1 110.17(13) . . ?
C4 C13 H13A 108.7 . . ?
C4 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
O1 C13 C4 114.23(12) . . ?
O1 C13 H13A 108.7 . . ?
O1 C13 H13B 108.7 . . ?
C5 C14 H14A 108.9 . . ?
C5 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
O1 C14 C5 113.25(12) . . ?
O1 C14 H14A 108.9 . . ?
O1 C14 H14B 108.9 . . ?
C16 C15 H15 106.6 . . ?
C16 C15 Si1 109.34(16) . . ?
C17 C15 H15 106.6 . . ?
C17 C15 C16 111.1(2) . . ?
C17 C15 Si1 116.14(15) . . ?
Si1 C15 H15 106.6 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 H18 105.9 . . ?
C19 C18 C20 110.84(17) . . ?
C19 C18 Si1 113.97(13) . . ?
C20 C18 H18 105.9 . . ?
C20 C18 Si1 113.52(14) . . ?
Si1 C18 H18 105.9 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 H21 106.6 . . ?
C22 C21 C23 109.62(14) . . ?
C22 C21 Si1 114.66(12) . . ?
C23 C21 H21 106.6 . . ?
C23 C21 Si1 112.25(11) . . ?
Si1 C21 H21 106.6 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C9 N1 C12 105.68(12) . . ?
C9 N1 Si1 130.28(10) . . ?
C12 N1 Si1 123.89(10) . . ?
C13 O1 C14 113.90(11) . . ?
C15 Si1 C18 107.04(9) . . ?
C15 Si1 C21 111.31(9) . . ?
C21 Si1 C18 111.11(8) . . ?
N1 Si1 C15 108.40(7) . . ?
N1 Si1 C18 109.82(7) . . ?
N1 Si1 C21 109.11(7) . . ?

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
C1 C2 C3 C4 -2.4(3) . . . . ?
C1 C9 C10 C4 -3.0(2) . . . . ?
C1 C9 C10 C11 176.26(14) . . . . ?
C1 C9 N1 C12 -175.90(17) . . . . ?
C1 C9 N1 Si1 -0.3(3) . . . . ?
C2 C1 C9 C10 1.8(3) . . . . ?
C2 C1 C9 N1 -179.72(17) . . . . ?
C2 C3 C4 C10 1.3(2) . . . . ?
C2 C3 C4 C13 -176.96(15) . . . . ?
C3 C4 C10 C9 1.4(2) . . . . ?
C3 C4 C10 C11 -177.60(15) . . . . ?
C3 C4 C13 O1 -152.26(14) . . . . ?
C4 C10 C11 C5 3.2(3) . . . . ?
C4 C10 C11 C12 -179.57(15) . . . . ?
C4 C13 O1 C14 -81.39(15) . . . . ?
C5 C6 C7 C8 0.8(2) . . . . ?
C5 C11 C12 C8 -1.2(2) . . . . ?
C5 C11 C12 N1 177.89(13) . . . . ?
C5 C14 O1 C13 89.03(14) . . . . ?
C6 C5 C11 C10 178.73(14) . . . . ?
C6 C5 C11 C12 1.8(2) . . . . ?
C6 C5 C14 O1 142.16(14) . . . . ?
C6 C7 C8 C12 -0.2(2) . . . . ?
C7 C8 C12 C11 0.4(2) . . . . ?
C7 C8 C12 N1 -178.54(15) . . . . ?
C8 C12 N1 C9 177.17(15) . . . . ?
C8 C12 N1 Si1 1.2(2) . . . . ?
C9 C1 C2 C3 0.8(3) . . . . ?
C9 C10 C11 C5 -175.93(15) . . . . ?
C9 C10 C11 C12 1.33(16) . . . . ?
C9 N1 Si1 C15 -100.11(15) . . . . ?
C9 N1 Si1 C18 16.52(16) . . . . ?
C9 N1 Si1 C21 138.52(14) . . . . ?
C10 C4 C13 O1 29.6(2) . . . . ?
C10 C9 N1 C12 2.68(16) . . . . ?
C10 C9 N1 Si1 178.27(11) . . . . ?
C10 C11 C12 C8 -178.80(13) . . . . ?
C10 C11 C12 N1 0.31(16) . . . . ?
C11 C5 C6 C7 -1.6(2) . . . . ?
C11 C5 C14 O1 -39.72(18) . . . . ?
C11 C12 N1 C9 -1.82(16) . . . . ?
C11 C12 N1 Si1 -177.77(10) . . . . ?
C12 N1 Si1 C15 74.77(14) . . . . ?
C12 N1 Si1 C18 -168.60(12) . . . . ?
C12 N1 Si1 C21 -46.60(14) . . . . ?
C13 C4 C10 C9 179.58(14) . . . . ?
C13 C4 C10 C11 0.6(2) . . . . ?
C14 C5 C6 C7 176.59(14) . . . . ?
C14 C5 C11 C10 0.5(2) . . . . ?
C14 C5 C11 C12 -176.38(13) . . . . ?
C16 C15 Si1 C18 -63.76(18) . . . . ?
C16 C15 Si1 C21 174.64(16) . . . . ?
C16 C15 Si1 N1 54.64(18) . . . . ?
C17 C15 Si1 C18 169.51(15) . . . . ?
C17 C15 Si1 C21 47.91(17) . . . . ?
C17 C15 Si1 N1 -72.09(17) . . . . ?
C19 C18 Si1 C15 -175.36(13) . . . . ?
C19 C18 Si1 C21 -53.64(15) . . . . ?
C19 C18 Si1 N1 67.16(14) . . . . ?
C20 C18 Si1 C15 -47.18(17) . . . . ?
C20 C18 Si1 C21 74.55(17) . . . . ?
C20 C18 Si1 N1 -164.65(14) . . . . ?
C22 C21 Si1 C15 -159.90(12) . . . . ?
C22 C21 Si1 C18 80.90(14) . . . . ?
C22 C21 Si1 N1 -40.32(14) . . . . ?
C23 C21 Si1 C15 74.15(14) . . . . ?
C23 C21 Si1 C18 -45.05(15) . . . . ?
C23 C21 Si1 N1 -166.27(12) . . . . ?
N1 C9 C10 C4 178.27(13) . . . . ?
N1 C9 C10 C11 -2.52(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.215
_oxdiff_exptl_absorpt_empirical_full_min 0.868
####################################################################### 
# 
# 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_10b
_database_code_depnum_ccdc_archive 'CCDC 2079911'
loop_
_audit_author_name
_audit_author_address
'Louise Male'
;University of Birmingham
United Kingdom
;
_audit_update_record             
;
2021-04-25 deposited with the CCDC.	2021-06-18 downloaded from the CCDC.
;
_audit_creation_date             2019-07-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H7 N S2'
_chemical_formula_sum            'C12 H7 N S2'
_chemical_formula_weight         229.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H7 N1 S2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3372(6)
_cell_length_b                   10.5025(6)
_cell_length_c                   10.6156(6)
_cell_angle_alpha                92.683(4)
_cell_angle_beta                 108.926(5)
_cell_angle_gamma                91.966(5)
_cell_volume                     982.30(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4334
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.4420
_cell_measurement_theta_min      4.1720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.559
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 6 4 0.0719
-2 3 6 0.0757
0 -6 2 0.0578
2 0 -7 0.0593
2 2 -7 0.0577
6 0 0 0.0180
-5 0 -1 0.0343
1 4 -5 0.0762
5 1 -6 0.0484
-5 4 1 0.0613
-5 1 5 0.0656
3 -5 2 0.0460
-1 -1 7 0.0795
4 2 3 0.0394
-4 -5 1 0.0547
-1 2 -6 0.0542
-5 -3 3 0.0551
5 -1 2 0.0248

_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.058
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.0000 6.0000 4.0000 0.6901 0.8276 0.1059
-2.0000 3.0000 6.0000 0.5543 0.7296 -0.3885
-0.0000 -6.0000 2.0000 -0.3045 -0.4035 -0.7643
2.0000 0.0000 -7.0000 -0.4020 -0.5279 0.7707
2.0000 2.0000 -7.0000 -0.2896 -0.3242 0.9506
6.0000 -0.0000 0.0000 -0.8617 0.5947 -0.0448
-5.0000 0.0000 -1.0000 0.7017 -0.5993 0.1496
1.0000 4.0000 -5.0000 -0.0007 -0.0123 0.9136
5.0000 1.0000 -6.0000 -0.7602 -0.0250 0.7260
-5.0000 4.0000 1.0000 0.9594 0.0154 0.2850
-5.0000 1.0000 5.0000 0.8563 0.1249 -0.4338
3.0000 -5.0000 2.0000 -0.6792 -0.0043 -0.6968
-1.0000 -1.0000 7.0000 0.2022 0.5252 -0.8681
4.0000 2.0000 3.0000 -0.4128 0.9113 -0.1866
-4.0000 -5.0000 1.0000 0.3098 -0.8018 -0.5322
-1.0000 2.0000 -6.0000 0.1577 -0.5179 0.8608
-5.0000 -3.0000 3.0000 0.5986 -0.4899 -0.5693
5.0000 -1.0000 2.0000 -0.7415 0.6012 -0.3518

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6804
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.624
_diffrn_reflns_theta_min         4.220
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -113.00 -16.00   1.00    1.00    --  -42.56 -57.00 120.00   97
  2  ω    -86.00 -55.00   1.00    1.00    --  -42.56 125.00 -30.00   31
  3  ω    -65.00  30.00   1.00    1.00    --  -42.56  38.00  60.00   95
  4  ω    -61.00  25.00   1.00    1.00    --  -42.56  57.00 -90.00   86
  5  ω     40.00  65.00   1.00    1.89    --  106.63 -30.00  30.00   25
  6  ω     42.00 127.00   1.00    1.89    --  106.63 -30.00 -60.00   85
  7  ω     32.00 130.00   1.00    1.89    --  106.63 -30.00 120.00   98
  8  ω     36.00  86.00   1.00    1.89    --  106.63-125.00 120.00   50
  9  ω     36.00 130.00   1.00    1.89    --  106.63 -30.00-150.00   94
 10  ω     90.00 118.00   1.00    1.89    --  106.63-125.00 120.00   28
 11  ω    130.00 177.00   1.00    1.89    --  106.63  45.00 -90.00   47
 12  ω     95.00 123.00   1.00    1.89    --  106.63 -30.00  30.00   28
 13  ω     66.00 118.00   1.00    1.89    --  106.63-125.00 -90.00   52
 14  ω    143.00 175.00   1.00    1.89    --  106.63 125.00 150.00   32
 15  ω     98.00 123.00   1.00    1.89    --  106.63 125.00 150.00   25
 16  ω     40.00  94.00   1.00    1.89    --  106.63 -94.00-180.00   54
 17  ω    128.00 178.00   1.00    1.89    --  106.63 125.00-120.00   50
 18  ω     34.00 108.00   1.00    1.89    --  106.63 -77.00 -90.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1436187000
_diffrn_orient_matrix_UB_12      0.0562210000
_diffrn_orient_matrix_UB_13      0.0163961000
_diffrn_orient_matrix_UB_21      0.0991179000
_diffrn_orient_matrix_UB_22      0.1018183000
_diffrn_orient_matrix_UB_23      0.1037296000
_diffrn_orient_matrix_UB_31      -0.0074735000
_diffrn_orient_matrix_UB_32      0.0899748000
_diffrn_orient_matrix_UB_33      -0.1122351000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3473
_reflns_number_total             3862
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         3862
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0292
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0371P)²+0.4707P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0776
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C101(H101), C102(H102),
 C103(H103), C106(H106), C107(H107), C108(H108)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2010(2) 1.02013(17) 0.68057(18) 0.0198(4) Uani 1 1 d . . . . .
H1 H 0.201846 1.084044 0.623037 0.024 Uiso 1 1 calc R . . . .
C2 C 0.0666(2) 0.97010(18) 0.69106(18) 0.0211(4) Uani 1 1 d . . . . .
H2 H -0.023947 0.999910 0.636698 0.025 Uiso 1 1 calc R . . . .
C3 C 0.0600(2) 0.87625(17) 0.77992(18) 0.0189(4) Uani 1 1 d . . . . .
H3 H -0.032658 0.846623 0.785371 0.023 Uiso 1 1 calc R . . . .
C4 C 0.19460(19) 0.82874(16) 0.85932(16) 0.0149(3) Uani 1 1 d . . . . .
C5 C 0.5353(2) 0.74874(16) 1.00180(17) 0.0154(3) Uani 1 1 d . . . . .
C6 C 0.6907(2) 0.73851(17) 1.05405(18) 0.0195(4) Uani 1 1 d . . . . .
H6 H 0.730868 0.677838 1.115151 0.023 Uiso 1 1 calc R . . . .
C7 C 0.7869(2) 0.82134(18) 1.01333(19) 0.0217(4) Uani 1 1 d . . . . .
H7 H 0.891094 0.813617 1.048779 0.026 Uiso 1 1 calc R . . . .
C8 C 0.7336(2) 0.91397(17) 0.92275(19) 0.0201(4) Uani 1 1 d . . . . .
H8 H 0.799766 0.966097 0.896168 0.024 Uiso 1 1 calc R . . . .
C10 C 0.3356(2) 0.97069(16) 0.76004(17) 0.0157(3) Uani 1 1 d . . . . .
C11 C 0.32919(19) 0.87305(16) 0.84417(16) 0.0138(3) Uani 1 1 d . . . . .
C12 C 0.48058(19) 0.84370(16) 0.91422(16) 0.0138(3) Uani 1 1 d . . . . .
C13 C 0.5768(2) 0.92593(16) 0.87300(17) 0.0157(3) Uani 1 1 d . . . . .
N1 N 0.48662(18) 1.00284(14) 0.78045(15) 0.0174(3) Uani 1 1 d . . . . .
S1 S 0.21123(5) 0.73942(4) 1.00151(4) 0.01713(11) Uani 1 1 d . . . . .
S2 S 0.39961(5) 0.63296(4) 1.01717(4) 0.01799(11) Uani 1 1 d . . . . .
C101 C 0.7030(2) 0.48232(17) 0.35682(18) 0.0189(4) Uani 1 1 d . . . . .
H101 H 0.738211 0.409736 0.325445 0.023 Uiso 1 1 calc R . . . .
C102 C 0.8020(2) 0.57784(18) 0.43680(18) 0.0209(4) Uani 1 1 d . . . . .
H102 H 0.905591 0.568688 0.457169 0.025 Uiso 1 1 calc R . . . .
C103 C 0.7532(2) 0.68790(17) 0.48860(17) 0.0188(4) Uani 1 1 d . . . . .
H103 H 0.823514 0.748888 0.542929 0.023 Uiso 1 1 calc R . . . .
C104 C 0.5994(2) 0.70420(16) 0.45771(16) 0.0153(3) Uani 1 1 d . . . . .
C105 C 0.23575(19) 0.69254(16) 0.33964(16) 0.0144(3) Uani 1 1 d . . . . .
C106 C 0.0823(2) 0.66076(17) 0.28387(18) 0.0182(3) Uani 1 1 d . . . . .
H106 H 0.010947 0.717078 0.292776 0.022 Uiso 1 1 calc R . . . .
C107 C 0.0360(2) 0.54091(18) 0.21304(18) 0.0203(4) Uani 1 1 d . . . . .
H107 H -0.067249 0.519506 0.176500 0.024 Uiso 1 1 calc R . . . .
C108 C 0.1370(2) 0.45389(17) 0.19548(18) 0.0186(4) Uani 1 1 d . . . . .
H108 H 0.103382 0.377065 0.145598 0.022 Uiso 1 1 calc R . . . .
C110 C 0.5479(2) 0.50027(16) 0.32562(17) 0.0156(3) Uani 1 1 d . . . . .
C111 C 0.49890(19) 0.61202(16) 0.37382(16) 0.0141(3) Uani 1 1 d . . . . .
C112 C 0.33812(19) 0.60355(16) 0.32885(16) 0.0139(3) Uani 1 1 d . . . . .
C113 C 0.2915(2) 0.48607(16) 0.25565(17) 0.0155(3) Uani 1 1 d . . . . .
N101 N 0.42044(17) 0.42460(14) 0.25486(15) 0.0166(3) Uani 1 1 d . . . . .
S101 S 0.52184(5) 0.82140(4) 0.53996(4) 0.01790(11) Uani 1 1 d . . . . .
S102 S 0.31192(5) 0.85036(4) 0.39864(4) 0.01585(10) Uani 1 1 d . . . . .
H10A H 0.422(3) 0.351(3) 0.215(3) 0.035(7) Uiso 1 1 d . . . . .
H1A H 0.524(3) 1.061(3) 0.745(3) 0.034(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.383(3) . ?
C1 C10 1.400(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.409(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(2) . ?
C4 C11 1.386(2) . ?
C4 S1 1.7814(17) . ?
C5 C6 1.385(2) . ?
C5 C12 1.391(2) . ?
C5 S2 1.7767(18) . ?
C6 H6 0.9300 . ?
C6 C7 1.409(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.389(3) . ?
C8 H8 0.9300 . ?
C8 C13 1.398(3) . ?
C10 C11 1.403(2) . ?
C10 N1 1.382(2) . ?
C11 C12 1.420(2) . ?
C12 C13 1.408(2) . ?
C13 N1 1.383(2) . ?
N1 H1A 0.86(3) . ?
S1 S2 2.0819(6) . ?
C101 H101 0.9300 . ?
C101 C102 1.389(3) . ?
C101 C110 1.398(2) . ?
C102 H102 0.9300 . ?
C102 C103 1.409(3) . ?
C103 H103 0.9300 . ?
C103 C104 1.384(2) . ?
C104 C111 1.388(2) . ?
C104 S101 1.7814(18) . ?
C105 C106 1.383(2) . ?
C105 C112 1.387(2) . ?
C105 S102 1.7828(17) . ?
C106 H106 0.9300 . ?
C106 C107 1.414(3) . ?
C107 H107 0.9300 . ?
C107 C108 1.385(3) . ?
C108 H108 0.9300 . ?
C108 C113 1.397(2) . ?
C110 C111 1.408(2) . ?
C110 N101 1.383(2) . ?
C111 C112 1.418(2) . ?
C112 C113 1.403(2) . ?
C113 N101 1.388(2) . ?
N101 H10A 0.87(3) . ?
S101 S102 2.0883(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 121.3 . . ?
C2 C1 C10 117.32(16) . . ?
C10 C1 H1 121.3 . . ?
C1 C2 H2 118.3 . . ?
C1 C2 C3 123.34(17) . . ?
C3 C2 H2 118.3 . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.81(17) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 S1 124.23(14) . . ?
C11 C4 C3 118.27(16) . . ?
C11 C4 S1 116.29(13) . . ?
C6 C5 C12 118.41(16) . . ?
C6 C5 S2 124.03(13) . . ?
C12 C5 S2 116.73(13) . . ?
C5 C6 H6 120.5 . . ?
C5 C6 C7 119.07(16) . . ?
C7 C6 H6 120.5 . . ?
C6 C7 H7 118.4 . . ?
C8 C7 C6 123.10(17) . . ?
C8 C7 H7 118.4 . . ?
C7 C8 H8 121.2 . . ?
C7 C8 C13 117.52(17) . . ?
C13 C8 H8 121.2 . . ?
C1 C10 C11 119.52(16) . . ?
N1 C10 C1 132.53(16) . . ?
N1 C10 C11 107.87(15) . . ?
C4 C11 C10 122.53(16) . . ?
C4 C11 C12 129.69(16) . . ?
C10 C11 C12 107.47(15) . . ?
C5 C12 C11 130.15(16) . . ?
C5 C12 C13 122.44(16) . . ?
C13 C12 C11 107.28(15) . . ?
C8 C13 C12 119.40(16) . . ?
N1 C13 C8 132.76(16) . . ?
N1 C13 C12 107.76(15) . . ?
C10 N1 C13 109.60(14) . . ?
C10 N1 H1A 128.3(17) . . ?
C13 N1 H1A 122.1(17) . . ?
C4 S1 S2 103.29(6) . . ?
C5 S2 S1 102.86(6) . . ?
C102 C101 H101 121.5 . . ?
C102 C101 C110 116.96(17) . . ?
C110 C101 H101 121.5 . . ?
C101 C102 H102 118.4 . . ?
C101 C102 C103 123.27(17) . . ?
C103 C102 H102 118.4 . . ?
C102 C103 H103 120.4 . . ?
C104 C103 C102 119.22(17) . . ?
C104 C103 H103 120.4 . . ?
C103 C104 C111 118.27(16) . . ?
C103 C104 S101 123.79(14) . . ?
C111 C104 S101 117.09(13) . . ?
C106 C105 C112 118.74(16) . . ?
C106 C105 S102 123.75(13) . . ?
C112 C105 S102 116.53(13) . . ?
C105 C106 H106 120.7 . . ?
C105 C106 C107 118.66(17) . . ?
C107 C106 H106 120.7 . . ?
C106 C107 H107 118.4 . . ?
C108 C107 C106 123.16(17) . . ?
C108 C107 H107 118.4 . . ?
C107 C108 H108 121.3 . . ?
C107 C108 C113 117.36(16) . . ?
C113 C108 H108 121.3 . . ?
C101 C110 C111 119.89(16) . . ?
N101 C110 C101 132.43(17) . . ?
N101 C110 C111 107.65(15) . . ?
C104 C111 C110 122.30(16) . . ?
C104 C111 C112 129.93(16) . . ?
C110 C111 C112 107.62(15) . . ?
C105 C112 C111 130.29(16) . . ?
C105 C112 C113 122.18(16) . . ?
C113 C112 C111 107.33(15) . . ?
C108 C113 C112 119.74(16) . . ?
N101 C113 C108 132.31(17) . . ?
N101 C113 C112 107.89(15) . . ?
C110 N101 C113 109.50(15) . . ?
C110 N101 H10A 124.5(17) . . ?
C113 N101 H10A 126.0(17) . . ?
C104 S101 S102 103.23(6) . . ?
C105 S102 S101 103.57(6) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A S102 0.86(3) 2.66(3) 3.4533(15) 155(2) 2_676 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
C1 C2 C3 C4 -1.6(3) . . . . ?
C1 C10 C11 C4 -4.6(3) . . . . ?
C1 C10 C11 C12 -178.77(16) . . . . ?
C1 C10 N1 C13 178.23(19) . . . . ?
C2 C1 C10 C11 0.9(3) . . . . ?
C2 C1 C10 N1 -175.51(18) . . . . ?
C2 C3 C4 C11 -2.1(3) . . . . ?
C2 C3 C4 S1 164.87(14) . . . . ?
C3 C4 C11 C10 5.2(3) . . . . ?
C3 C4 C11 C12 177.92(17) . . . . ?
C3 C4 S1 S2 155.02(14) . . . . ?
C4 C11 C12 C5 11.4(3) . . . . ?
C4 C11 C12 C13 -172.56(17) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C5 C12 C13 C8 -1.0(3) . . . . ?
C5 C12 C13 N1 176.28(15) . . . . ?
C6 C5 C12 C11 178.06(17) . . . . ?
C6 C5 C12 C13 2.6(3) . . . . ?
C6 C5 S2 S1 154.48(14) . . . . ?
C6 C7 C8 C13 1.4(3) . . . . ?
C7 C8 C13 C12 -1.0(2) . . . . ?
C7 C8 C13 N1 -177.46(18) . . . . ?
C8 C13 N1 C10 175.86(18) . . . . ?
C10 C1 C2 C3 2.1(3) . . . . ?
C10 C11 C12 C5 -174.98(17) . . . . ?
C10 C11 C12 C13 1.03(19) . . . . ?
C11 C4 S1 S2 -37.79(14) . . . . ?
C11 C10 N1 C13 1.54(19) . . . . ?
C11 C12 C13 C8 -177.36(15) . . . . ?
C11 C12 C13 N1 -0.10(19) . . . . ?
C12 C5 C6 C7 -2.1(3) . . . . ?
C12 C5 S2 S1 -36.14(14) . . . . ?
C12 C13 N1 C10 -0.89(19) . . . . ?
N1 C10 C11 C4 172.58(16) . . . . ?
N1 C10 C11 C12 -1.57(19) . . . . ?
S1 C4 C11 C10 -162.80(13) . . . . ?
S1 C4 C11 C12 9.9(3) . . . . ?
S2 C5 C6 C7 167.08(14) . . . . ?
S2 C5 C12 C11 8.1(3) . . . . ?
S2 C5 C12 C13 -167.42(13) . . . . ?
C101 C102 C103 C104 -1.0(3) . . . . ?
C101 C110 C111 C104 -3.2(2) . . . . ?
C101 C110 C111 C112 -179.11(15) . . . . ?
C101 C110 N101 C113 178.51(17) . . . . ?
C102 C101 C110 C111 0.7(2) . . . . ?
C102 C101 C110 N101 -177.01(17) . . . . ?
C102 C103 C104 C111 -1.4(2) . . . . ?
C102 C103 C104 S101 167.71(13) . . . . ?
C103 C104 C111 C110 3.5(2) . . . . ?
C103 C104 C111 C112 178.48(16) . . . . ?
C103 C104 S101 S102 155.44(13) . . . . ?
C104 C111 C112 C105 10.5(3) . . . . ?
C104 C111 C112 C113 -174.67(16) . . . . ?
C105 C106 C107 C108 -0.7(3) . . . . ?
C105 C112 C113 C108 -2.7(2) . . . . ?
C105 C112 C113 N101 174.88(15) . . . . ?
C106 C105 C112 C111 178.62(16) . . . . ?
C106 C105 C112 C113 4.4(2) . . . . ?
C106 C105 S102 S101 155.37(14) . . . . ?
C106 C107 C108 C113 2.4(3) . . . . ?
C107 C108 C113 C112 -0.8(2) . . . . ?
C107 C108 C113 N101 -177.60(17) . . . . ?
C108 C113 N101 C110 177.01(18) . . . . ?
C110 C101 C102 C103 1.4(3) . . . . ?
C110 C111 C112 C105 -173.98(16) . . . . ?
C110 C111 C112 C113 0.87(18) . . . . ?
C111 C104 S101 S102 -35.30(13) . . . . ?
C111 C110 N101 C113 0.63(18) . . . . ?
C111 C112 C113 C108 -178.01(15) . . . . ?
C111 C112 C113 N101 -0.48(18) . . . . ?
C112 C105 C106 C107 -2.7(2) . . . . ?
C112 C105 S102 S101 -36.13(13) . . . . ?
C112 C113 N101 C110 -0.09(18) . . . . ?
N101 C110 C111 C104 175.03(15) . . . . ?
N101 C110 C111 C112 -0.92(18) . . . . ?
S101 C104 C111 C110 -166.36(12) . . . . ?
S101 C104 C111 C112 8.6(2) . . . . ?
S102 C105 C106 C107 165.53(13) . . . . ?
S102 C105 C112 C111 9.5(2) . . . . ?
S102 C105 C112 C113 -164.67(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.435
_oxdiff_exptl_absorpt_empirical_full_min 0.810
