# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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. 
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#######################################################################

data_ntc-013
_database_code_depnum_ccdc_archive 'CCDC 2176810'
loop_
_audit_author_name
_audit_author_address
'Nathan Coles'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2022-06-03 deposited with the CCDC.	2022-11-03 downloaded from the CCDC.
;
_audit_creation_date             2021-08-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
N.T.Coles@fu-berlin.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 F6 P Si'
_chemical_formula_sum            'C16 H15 F6 P Si'
_chemical_formula_weight         380.34
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   10.4653(2)
_cell_length_b                   10.4653(2)
_cell_length_c                   31.2709(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3424.87(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.76
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   0.955
_shelx_estimated_absorpt_T_min   0.925
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  0.9708
_exptl_absorpt_correction_T_min  0.9254
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0785 before and 0.0638 after correction.
The Ratio of minimum to maximum transmission is 0.9532.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1552
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 5.00 -1.00 0.0700
0.00 5.00 -4.00 0.0820
2.00 -1.00 -4.00 0.1220
1.00 -3.00 0.00 0.1180
-1.00 -1.00 3.00 0.0850
-5.00 -5.00 -2.00 0.0510
-1.00 2.00 -3.00 0.0510
3.00 0.00 4.00 0.1390
3.00 -1.00 5.00 0.1320
1.00 -2.00 -2.00 0.1120
-1.00 -1.00 4.00 0.0890
2.00 0.00 -3.00 0.1110
-1.00 -2.00 3.00 0.0880
1.00 1.00 9.00 0.0810
-1.00 -1.00 -9.00 0.0720
0.00 0.00 1.00 0.0820
0.00 0.00 -1.00 0.0820

_exptl_crystal_size_max          0.279
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.164
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            63344
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.517
_diffrn_reflns_theta_min         2.342
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4533
_reflns_number_total             5224
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 1716 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         5224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0349
_refine_ls_restrained_S_all      1.080
_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)+(0.0335P)²+1.5088P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0863
_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 Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_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
P1 P 0.38226(6) 0.86722(6) 0.44646(2) 0.01894(13) Uani 1 1 d . . . . .
Si1 Si 0.44533(6) 0.62711(6) 0.39496(2) 0.01666(13) Uani 1 1 d . . . . .
F1 F 0.36870(17) 1.09190(15) 0.53306(5) 0.0316(4) Uani 1 1 d . . . . .
F2 F 0.25357(16) 1.07712(17) 0.47669(5) 0.0347(4) Uani 1 1 d . . . . .
F3 F 0.40712(18) 1.21173(15) 0.47828(5) 0.0346(4) Uani 1 1 d . . . . .
F4 F 0.60936(18) 1.15674(16) 0.53006(5) 0.0359(4) Uani 1 1 d . . . . .
F5 F 0.6735(2) 1.20983(17) 0.46727(6) 0.0424(5) Uani 1 1 d . . . . .
F6 F 0.78522(17) 1.08257(18) 0.50580(7) 0.0450(5) Uani 1 1 d . . . . .
C1 C 0.5042(2) 0.7661(2) 0.42975(7) 0.0156(4) Uani 1 1 d . . . . .
C2 C 0.6332(2) 0.7914(2) 0.43869(7) 0.0163(4) Uani 1 1 d . . . . .
C3 C 0.6752(2) 0.9033(2) 0.45954(7) 0.0195(5) Uani 1 1 d . . . . .
H3 H 0.764682 0.914317 0.463183 0.023 Uiso 1 1 calc R U . . .
C4 C 0.5951(2) 0.9988(2) 0.47515(7) 0.0196(5) Uani 1 1 d . . . . .
C5 C 0.4623(2) 0.9917(2) 0.47202(7) 0.0189(5) Uani 1 1 d . . . . .
C6 C 0.7357(2) 0.7005(2) 0.42545(7) 0.0168(4) Uani 1 1 d . . . . .
C7 C 0.7387(2) 0.5763(2) 0.44188(8) 0.0192(4) Uani 1 1 d . . . . .
H7 H 0.676114 0.549994 0.462030 0.023 Uiso 1 1 calc R U . . .
C8 C 0.8330(2) 0.4913(2) 0.42887(8) 0.0222(5) Uani 1 1 d . . . . .
H8 H 0.834742 0.407002 0.440159 0.027 Uiso 1 1 calc R U . . .
C9 C 0.9245(2) 0.5292(3) 0.39942(8) 0.0245(5) Uani 1 1 d . . . . .
H9 H 0.988207 0.470506 0.390280 0.029 Uiso 1 1 calc R U . . .
C10 C 0.9232(2) 0.6527(3) 0.38329(8) 0.0239(5) Uani 1 1 d . . . . .
H10 H 0.986402 0.678753 0.363312 0.029 Uiso 1 1 calc R U . . .
C11 C 0.8294(2) 0.7382(2) 0.39636(8) 0.0205(5) Uani 1 1 d . . . . .
H11 H 0.829139 0.822898 0.385407 0.025 Uiso 1 1 calc R U . . .
C12 C 0.6654(3) 1.1118(3) 0.49494(9) 0.0280(6) Uani 1 1 d . . . . .
C13 C 0.3739(3) 1.0935(2) 0.49018(8) 0.0248(5) Uani 1 1 d . . . . .
C14 C 0.4298(3) 0.4757(2) 0.42623(9) 0.0263(5) Uani 1 1 d . . . . .
H14A H 0.514675 0.438336 0.430644 0.039 Uiso 1 1 calc R U . . .
H14B H 0.376090 0.415258 0.410438 0.039 Uiso 1 1 calc R U . . .
H14C H 0.390596 0.494127 0.454013 0.039 Uiso 1 1 calc R U . . .
C15 C 0.5508(2) 0.6049(3) 0.34721(8) 0.0238(5) Uani 1 1 d . . . . .
H15A H 0.562046 0.686995 0.332611 0.036 Uiso 1 1 calc R U . . .
H15B H 0.511418 0.543492 0.327561 0.036 Uiso 1 1 calc R U . . .
H15C H 0.634265 0.572553 0.356444 0.036 Uiso 1 1 calc R U . . .
C16 C 0.2839(2) 0.6718(3) 0.37450(8) 0.0248(5) Uani 1 1 d . . . . .
H16A H 0.227155 0.690098 0.398658 0.037 Uiso 1 1 calc R U . . .
H16B H 0.248795 0.600871 0.357733 0.037 Uiso 1 1 calc R U . . .
H16C H 0.291005 0.747790 0.356354 0.037 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C1 1.739(2) . ?
P1 C5 1.743(2) . ?
Si1 C1 1.918(2) . ?
Si1 C14 1.869(3) . ?
Si1 C15 1.872(2) . ?
Si1 C16 1.866(3) . ?
F1 C13 1.342(3) . ?
F2 C13 1.339(3) . ?
F3 C13 1.338(3) . ?
F4 C12 1.331(3) . ?
F5 C12 1.345(3) . ?
F6 C12 1.335(3) . ?
C1 C2 1.403(3) . ?
C2 C3 1.411(3) . ?
C2 C6 1.492(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(3) . ?
C4 C5 1.396(3) . ?
C4 C12 1.524(3) . ?
C5 C13 1.521(3) . ?
C6 C7 1.398(3) . ?
C6 C11 1.395(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.390(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(3) . ?
C11 H11 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 C5 103.89(11) . . ?
C14 Si1 C1 111.96(11) . . ?
C14 Si1 C15 111.30(12) . . ?
C15 Si1 C1 110.92(11) . . ?
C16 Si1 C1 107.19(11) . . ?
C16 Si1 C14 108.25(12) . . ?
C16 Si1 C15 106.95(12) . . ?
P1 C1 Si1 113.34(12) . . ?
C2 C1 P1 122.09(17) . . ?
C2 C1 Si1 124.41(17) . . ?
C1 C2 C3 123.3(2) . . ?
C1 C2 C6 121.1(2) . . ?
C3 C2 C6 115.6(2) . . ?
C2 C3 H3 117.6 . . ?
C4 C3 C2 124.7(2) . . ?
C4 C3 H3 117.6 . . ?
C3 C4 C5 122.5(2) . . ?
C3 C4 C12 114.1(2) . . ?
C5 C4 C12 123.4(2) . . ?
C4 C5 P1 123.42(18) . . ?
C4 C5 C13 122.8(2) . . ?
C13 C5 P1 113.74(18) . . ?
C7 C6 C2 120.4(2) . . ?
C11 C6 C2 120.4(2) . . ?
C11 C6 C7 119.2(2) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.3(2) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.1(2) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.1(2) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
C6 C11 H11 119.8 . . ?
C10 C11 C6 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
F4 C12 F5 106.8(2) . . ?
F4 C12 F6 106.6(2) . . ?
F4 C12 C4 113.4(2) . . ?
F5 C12 C4 111.2(2) . . ?
F6 C12 F5 106.2(2) . . ?
F6 C12 C4 112.3(2) . . ?
F1 C13 C5 112.9(2) . . ?
F2 C13 F1 106.0(2) . . ?
F2 C13 C5 111.4(2) . . ?
F3 C13 F1 107.5(2) . . ?
F3 C13 F2 106.0(2) . . ?
F3 C13 C5 112.7(2) . . ?
Si1 C14 H14A 109.5 . . ?
Si1 C14 H14B 109.5 . . ?
Si1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
Si1 C15 H15A 109.5 . . ?
Si1 C15 H15B 109.5 . . ?
Si1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Si1 C16 H16A 109.5 . . ?
Si1 C16 H16B 109.5 . . ?
Si1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C1 C2 C3 -3.8(3) . . . . ?
P1 C1 C2 C6 177.63(17) . . . . ?
P1 C5 C13 F1 108.9(2) . . . . ?
P1 C5 C13 F2 -10.2(3) . . . . ?
P1 C5 C13 F3 -129.1(2) . . . . ?
Si1 C1 C2 C3 171.28(17) . . . . ?
Si1 C1 C2 C6 -7.3(3) . . . . ?
C1 P1 C5 C4 1.5(2) . . . . ?
C1 P1 C5 C13 -179.34(17) . . . . ?
C1 C2 C3 C4 2.7(4) . . . . ?
C1 C2 C6 C7 -62.4(3) . . . . ?
C1 C2 C6 C11 117.2(3) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
C2 C3 C4 C12 -178.0(2) . . . . ?
C2 C6 C7 C8 178.8(2) . . . . ?
C2 C6 C11 C10 -178.5(2) . . . . ?
C3 C2 C6 C7 118.9(2) . . . . ?
C3 C2 C6 C11 -61.4(3) . . . . ?
C3 C4 C5 P1 -2.8(3) . . . . ?
C3 C4 C5 C13 178.1(2) . . . . ?
C3 C4 C12 F4 -140.5(2) . . . . ?
C3 C4 C12 F5 99.2(3) . . . . ?
C3 C4 C12 F6 -19.6(3) . . . . ?
C4 C5 C13 F1 -72.0(3) . . . . ?
C4 C5 C13 F2 169.0(2) . . . . ?
C4 C5 C13 F3 50.0(3) . . . . ?
C5 P1 C1 Si1 -173.90(12) . . . . ?
C5 P1 C1 C2 1.7(2) . . . . ?
C5 C4 C12 F4 40.7(4) . . . . ?
C5 C4 C12 F5 -79.6(3) . . . . ?
C5 C4 C12 F6 161.6(2) . . . . ?
C6 C2 C3 C4 -178.7(2) . . . . ?
C6 C7 C8 C9 -0.1(4) . . . . ?
C7 C6 C11 C10 1.2(4) . . . . ?
C7 C8 C9 C10 0.8(4) . . . . ?
C8 C9 C10 C11 -0.6(4) . . . . ?
C9 C10 C11 C6 -0.4(4) . . . . ?
C11 C6 C7 C8 -0.9(3) . . . . ?
C12 C4 C5 P1 175.89(19) . . . . ?
C12 C4 C5 C13 -3.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ntc-155
_database_code_depnum_ccdc_archive 'CCDC 2176812'
loop_
_audit_author_name
_audit_author_address
'Nathan Coles'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2022-06-03 deposited with the CCDC.	2022-11-03 downloaded from the CCDC.
;
_audit_creation_date             2021-07-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
N.T.Coles@fu-berlin.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H12 F3 N2 P'
_chemical_formula_sum            'C10 H12 F3 N2 P'
_chemical_formula_weight         248.19
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   12.2387(8)
_cell_length_b                   11.0061(7)
_cell_length_c                   8.6295(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.664(2)
_cell_angle_gamma                90
_cell_volume                     1156.72(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.46
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.920
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8660
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1025 before and 0.0677 after correction.
The Ratio of minimum to maximum transmission is 0.8660.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             512
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4.00 -3.00 0.00 0.0650
-2.00 -6.00 -5.00 0.1120
5.00 0.00 -4.00 0.1440
4.00 3.00 0.00 0.0650
2.00 6.00 5.00 0.0730
-1.00 5.00 3.00 0.0730
3.00 1.00 6.00 0.1100
-1.00 2.00 0.00 0.0940
-3.00 0.00 -5.00 0.1430
2.00 -5.00 -1.00 0.1030
6.00 -9.00 2.00 0.0990
1.00 6.00 2.00 0.0370
2.00 9.00 1.00 0.0460
-2.00 -8.00 1.00 0.0570
1.00 2.00 -4.00 0.1580
-2.00 -9.00 0.00 0.0600
2.00 5.00 1.00 0.0420
3.00 9.00 4.00 0.0410
-1.00 -2.00 0.00 0.0500
7.00 3.00 0.00 0.0710
-5.00 -2.00 0.00 0.0760
-7.00 -2.00 1.00 0.0740
-4.00 2.00 1.00 0.0770
-9.00 -4.00 -6.00 0.1130
8.00 -1.00 1.00 0.0940
9.00 -7.00 -5.00 0.1310

_exptl_crystal_size_max          0.337
_exptl_crystal_size_mid          0.229
_exptl_crystal_size_min          0.116
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19732
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.572
_diffrn_reflns_theta_min         2.494
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.989
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                3321
_reflns_number_total             3536
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 1499 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         3536
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.084
_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)+(0.0569P)²+1.2038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1171
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C3(H3)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_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
P1 P 0.67658(7) 0.80756(7) 0.49105(8) 0.02244(18) Uani 1 1 d . . . . .
F1 F 0.4267(2) 0.5002(2) 0.5209(4) 0.0554(8) Uani 1 1 d . . . . .
F2 F 0.3494(3) 0.6414(3) 0.6333(4) 0.0630(9) Uani 1 1 d . . . . .
F3 F 0.2999(3) 0.6041(4) 0.3973(5) 0.0888(15) Uani 1 1 d . . . . .
N1 N 0.6090(3) 0.6217(3) 0.8009(3) 0.0265(6) Uani 1 1 d . . . . .
N2 N 0.6671(2) 0.5163(2) 0.5935(3) 0.0244(5) Uani 1 1 d . . . . .
H2 H 0.680416 0.516748 0.495137 0.029 Uiso 1 1 calc R U . . .
C1 C 0.6096(3) 0.8883(3) 0.3384(3) 0.0229(6) Uani 1 1 d . . . . .
H1 H 0.649773 0.951476 0.294931 0.027 Uiso 1 1 calc R U . . .
C2 C 0.5025(3) 0.8697(3) 0.2730(3) 0.0219(5) Uani 1 1 d . . . . .
C3 C 0.4360(3) 0.7810(3) 0.3309(4) 0.0241(6) Uani 1 1 d . . . . .
H3 H 0.362635 0.773684 0.284540 0.029 Uiso 1 1 calc R U . . .
C4 C 0.4707(3) 0.7022(3) 0.4526(4) 0.0228(6) Uani 1 1 d . . . . .
C5 C 0.5755(2) 0.7044(2) 0.5316(3) 0.0196(5) Uani 1 1 d . . . . .
C6 C 0.4573(3) 0.9465(3) 0.1354(4) 0.0293(7) Uani 1 1 d . . . . .
H6A H 0.383138 0.918706 0.098829 0.044 Uiso 1 1 calc R U . . .
H6B H 0.504975 0.938537 0.051196 0.044 Uiso 1 1 calc R U . . .
H6C H 0.454578 1.031773 0.167398 0.044 Uiso 1 1 calc R U . . .
C7 C 0.3870(3) 0.6110(3) 0.4986(4) 0.0310(7) Uani 1 1 d . . . . .
C8 C 0.6146(3) 0.6117(3) 0.6532(3) 0.0220(5) Uani 1 1 d . . . . .
C9 C 0.7012(3) 0.4139(3) 0.6923(4) 0.0314(7) Uani 1 1 d . . . . .
H9A H 0.741188 0.355569 0.633219 0.047 Uiso 1 1 calc R U . . .
H9B H 0.636406 0.374477 0.727828 0.047 Uiso 1 1 calc R U . . .
H9C H 0.749222 0.442481 0.782585 0.047 Uiso 1 1 calc R U . . .
C10 C 0.5574(4) 0.7281(3) 0.8616(4) 0.0338(8) Uani 1 1 d . . . . .
H10A H 0.531329 0.781930 0.775342 0.051 Uiso 1 1 calc R U . . .
H10B H 0.610995 0.771468 0.933367 0.051 Uiso 1 1 calc R U . . .
H10C H 0.495190 0.702757 0.917231 0.051 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C1 1.728(3) . ?
P1 C5 1.740(3) . ?
F1 C7 1.319(4) . ?
F2 C7 1.335(5) . ?
F3 C7 1.312(5) . ?
N1 C8 1.288(4) . ?
N1 C10 1.452(4) . ?
N2 H2 0.8800 . ?
N2 C8 1.358(4) . ?
N2 C9 1.450(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.390(4) . ?
C2 C3 1.395(4) . ?
C2 C6 1.516(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(4) . ?
C4 C5 1.392(4) . ?
C4 C7 1.515(4) . ?
C5 C8 1.508(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 C5 101.26(14) . . ?
C8 N1 C10 119.6(3) . . ?
C8 N2 H2 120.1 . . ?
C8 N2 C9 119.8(3) . . ?
C9 N2 H2 120.1 . . ?
P1 C1 H1 116.9 . . ?
C2 C1 P1 126.3(2) . . ?
C2 C1 H1 116.9 . . ?
C1 C2 C3 121.2(3) . . ?
C1 C2 C6 119.5(3) . . ?
C3 C2 C6 119.4(3) . . ?
C2 C3 H3 118.0 . . ?
C2 C3 C4 124.1(3) . . ?
C4 C3 H3 118.0 . . ?
C3 C4 C7 116.5(3) . . ?
C5 C4 C3 123.7(3) . . ?
C5 C4 C7 119.8(3) . . ?
C4 C5 P1 123.5(2) . . ?
C4 C5 C8 122.9(3) . . ?
C8 C5 P1 113.5(2) . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
F1 C7 F2 105.0(3) . . ?
F1 C7 C4 113.7(3) . . ?
F2 C7 C4 111.2(3) . . ?
F3 C7 F1 107.9(4) . . ?
F3 C7 F2 105.5(4) . . ?
F3 C7 C4 112.9(3) . . ?
N1 C8 N2 121.0(3) . . ?
N1 C8 C5 125.9(3) . . ?
N2 C8 C5 112.9(2) . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C1 C2 C3 1.4(4) . . . . ?
P1 C1 C2 C6 -178.0(2) . . . . ?
P1 C5 C8 N1 91.4(4) . . . . ?
P1 C5 C8 N2 -83.2(3) . . . . ?
C1 P1 C5 C4 -1.5(3) . . . . ?
C1 P1 C5 C8 174.5(2) . . . . ?
C1 C2 C3 C4 -2.1(5) . . . . ?
C2 C3 C4 C5 0.9(5) . . . . ?
C2 C3 C4 C7 -179.5(3) . . . . ?
C3 C4 C5 P1 1.1(4) . . . . ?
C3 C4 C5 C8 -174.5(3) . . . . ?
C3 C4 C7 F1 135.5(4) . . . . ?
C3 C4 C7 F2 -106.2(4) . . . . ?
C3 C4 C7 F3 12.2(5) . . . . ?
C4 C5 C8 N1 -92.6(4) . . . . ?
C4 C5 C8 N2 92.8(3) . . . . ?
C5 P1 C1 C2 0.3(3) . . . . ?
C5 C4 C7 F1 -44.8(5) . . . . ?
C5 C4 C7 F2 73.4(4) . . . . ?
C5 C4 C7 F3 -168.2(4) . . . . ?
C6 C2 C3 C4 177.3(3) . . . . ?
C7 C4 C5 P1 -178.5(2) . . . . ?
C7 C4 C5 C8 5.9(4) . . . . ?
C9 N2 C8 N1 10.6(5) . . . . ?
C9 N2 C8 C5 -174.5(3) . . . . ?
C10 N1 C8 N2 176.7(3) . . . . ?
C10 N1 C8 C5 2.4(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ntc043_1
_database_code_depnum_ccdc_archive 'CCDC 2176811'
loop_
_audit_author_name
_audit_author_address
'Nathan Coles'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2022-06-03 deposited with the CCDC.	2022-11-03 downloaded from the CCDC.
;
_audit_creation_date             2020-06-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
N.T.Coles@fu-berlin.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H25 P Si2'
_chemical_formula_sum            'C13 H25 P Si2'
_chemical_formula_weight         268.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.5114(3)
_cell_length_b                   13.5050(3)
_cell_length_c                   14.7354(3)
_cell_angle_alpha                85.5620(10)
_cell_angle_beta                 79.3630(10)
_cell_angle_gamma                86.7690(10)
_cell_volume                     2047.79(9)
_cell_formula_units_Z            5
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      32.62
_cell_measurement_theta_min      2.435
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.861
_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6453
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1320 before and 0.0629 after correction. The Ratio 
of minimum to maximum transmission is 0.8644. The λ/2 correction 
factor is Not present.'
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.089
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             730
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            54129
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.875
_diffrn_reflns_theta_min         1.997
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                10137
_reflns_number_total             13897
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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         0.636
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         13897
_refine_ls_number_restraints     35
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0453
_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)+(0.0379P)²+1.1544P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1166
_refine_special_details          
;The crystal shows 2.5 molecules of the compound per ASU, with one 
molecule being disordered about a special position. The molecule 
that is disordered consists of atoms P3, Si5/6 and C27-39. To give 
an acceptable model RIGU restraints were used for atoms P3 and C27-C31 
and DFIX restraints for P3-C27 and P3-C31 of 1.74 angstrom and for 
C27-Si5 and C31-Si6 of 1.9 angstrom. The DFIX distances used were 
taken as an average of the distances observed in the two molecules 
that did not show disorder.,Disorder
;
_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. Restrained distances
 P3-C27 = P3-C31
 1.74 with sigma of 0.02
 C27-Si5 = C31-Si6
 1.9 with sigma of 0.02
3. Rigid body (RIGU) restrains
 P3, C31, Si6, C27, Si5, C28, C30
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: P3(0.5) Si5(0.5) Si6(0.5) C27(0.5) C28(0.5) C29(0.5) H29(0.5)
 C30(0.5) C31(0.5) C32(0.5) H32A(0.5) H32B(0.5) H32C(0.5) C33(0.5) H33A(0.5)
 H33B(0.5) H33C(0.5) C34(0.5) H34A(0.5) H34B(0.5) H34C(0.5) C35(0.5) H35A(0.5)
 H35B(0.5) H35C(0.5) C36(0.5) H36A(0.5) H36B(0.5) H36C(0.5) C37(0.5) H37A(0.5)
 H37B(0.5) H37C(0.5) C38(0.5) H38A(0.5) H38B(0.5) H38C(0.5) C39(0.5) H39A(0.5)
 H39B(0.5) H39C(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C16(H16), C29(H29)
5.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,
 H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C),
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,
 H26B,H26C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C),
 C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,
 H38C), C39(H39A,H39B,H39C)
;
_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
P1 P 0.18219(4) 0.78103(3) 0.19860(3) 0.02221(9) Uani 1 1 d . . . . .
Si1 Si 0.27207(5) 0.69955(4) 0.00701(3) 0.02777(10) Uani 1 1 d . . . . .
Si2 Si 0.12278(4) 0.84933(3) 0.39678(3) 0.02305(9) Uani 1 1 d . . . . .
C1 C 0.27778(15) 0.69160(11) 0.13524(10) 0.0213(3) Uani 1 1 d . . . . .
C2 C 0.35441(15) 0.62009(11) 0.17762(10) 0.0222(3) Uani 1 1 d . . . . .
C3 C 0.35914(15) 0.61665(11) 0.27201(10) 0.0213(3) Uani 1 1 d . . . . .
H3 H 0.414152 0.566077 0.294556 0.026 Uiso 1 1 calc R U . . .
C4 C 0.29134(14) 0.67988(11) 0.33652(10) 0.0196(3) Uani 1 1 d . . . . .
C5 C 0.20768(14) 0.75839(11) 0.31184(10) 0.0192(3) Uani 1 1 d . . . . .
C6 C 0.4356(2) 0.54109(15) 0.12335(13) 0.0390(4) Uani 1 1 d . . . . .
H6A H 0.478133 0.570876 0.063463 0.058 Uiso 1 1 calc R U . . .
H6B H 0.379832 0.488718 0.113300 0.058 Uiso 1 1 calc R U . . .
H6C H 0.501382 0.512436 0.158101 0.058 Uiso 1 1 calc R U . . .
C7 C 0.31300(18) 0.65931(13) 0.43496(11) 0.0308(4) Uani 1 1 d . . . . .
H7A H 0.235878 0.630063 0.472907 0.046 Uiso 1 1 calc R U . . .
H7B H 0.329262 0.721657 0.459894 0.046 Uiso 1 1 calc R U . . .
H7C H 0.387909 0.612876 0.435903 0.046 Uiso 1 1 calc R U . . .
C8 C 0.21847(19) 0.58179(14) -0.03068(12) 0.0342(4) Uani 1 1 d . . . . .
H8A H 0.129633 0.569738 0.000957 0.051 Uiso 1 1 calc R U . . .
H8B H 0.276201 0.526131 -0.014960 0.051 Uiso 1 1 calc R U . . .
H8C H 0.221524 0.587882 -0.097741 0.051 Uiso 1 1 calc R U . . .
C9 C 0.4321(2) 0.73070(16) -0.06549(12) 0.0419(5) Uani 1 1 d . . . . .
H9A H 0.497454 0.678960 -0.053922 0.063 Uiso 1 1 calc R U . . .
H9B H 0.457707 0.794867 -0.049500 0.063 Uiso 1 1 calc R U . . .
H9C H 0.424934 0.734611 -0.131061 0.063 Uiso 1 1 calc R U . . .
C10 C 0.1517(3) 0.79966(18) -0.01852(15) 0.0596(7) Uani 1 1 d . . . . .
H10A H 0.178462 0.863561 -0.002739 0.089 Uiso 1 1 calc R U . . .
H10B H 0.066405 0.785108 0.018241 0.089 Uiso 1 1 calc R U . . .
H10C H 0.147018 0.802943 -0.084501 0.089 Uiso 1 1 calc R U . . .
C11 C 0.0209(2) 0.94189(17) 0.33840(14) 0.0496(6) Uani 1 1 d . . . . .
H11A H -0.044960 0.907448 0.315200 0.074 Uiso 1 1 calc R U . . .
H11B H 0.075689 0.977641 0.286553 0.074 Uiso 1 1 calc R U . . .
H11C H -0.021661 0.989247 0.382730 0.074 Uiso 1 1 calc R U . . .
C12 C 0.24465(19) 0.91905(14) 0.44207(13) 0.0358(4) Uani 1 1 d . . . . .
H12A H 0.309565 0.944425 0.390209 0.054 Uiso 1 1 calc R U . . .
H12B H 0.287345 0.874341 0.483928 0.054 Uiso 1 1 calc R U . . .
H12C H 0.200680 0.974802 0.475734 0.054 Uiso 1 1 calc R U . . .
C13 C 0.01283(18) 0.78609(15) 0.49604(13) 0.0365(4) Uani 1 1 d . . . . .
H13A H 0.063869 0.739114 0.530490 0.055 Uiso 1 1 calc R U . . .
H13B H -0.051348 0.750146 0.472502 0.055 Uiso 1 1 calc R U . . .
H13C H -0.031642 0.835884 0.537131 0.055 Uiso 1 1 calc R U . . .
P2 P 0.37774(4) 0.60772(3) 0.66482(3) 0.01908(8) Uani 1 1 d . . . . .
Si3 Si 0.14142(4) 0.47719(4) 0.70601(3) 0.02477(10) Uani 1 1 d . . . . .
Si4 Si 0.59178(4) 0.75847(3) 0.61791(3) 0.02265(9) Uani 1 1 d . . . . .
C14 C 0.21083(14) 0.60407(12) 0.70165(10) 0.0213(3) Uani 1 1 d . . . . .
C15 C 0.13530(15) 0.69185(13) 0.72300(10) 0.0246(3) Uani 1 1 d . . . . .
C16 C 0.18780(15) 0.78486(12) 0.71458(11) 0.0258(3) Uani 1 1 d . . . . .
H16 H 0.128988 0.839629 0.729795 0.031 Uiso 1 1 calc R U . . .
C17 C 0.31823(15) 0.80627(12) 0.68604(10) 0.0231(3) Uani 1 1 d . . . . .
C18 C 0.41528(14) 0.73184(11) 0.66104(10) 0.0200(3) Uani 1 1 d . . . . .
C19 C -0.00968(16) 0.68793(15) 0.75859(14) 0.0361(4) Uani 1 1 d . . . . .
H19A H -0.025241 0.663510 0.823899 0.054 Uiso 1 1 calc R U . . .
H19B H -0.047205 0.643041 0.722492 0.054 Uiso 1 1 calc R U . . .
H19C H -0.050064 0.754703 0.752340 0.054 Uiso 1 1 calc R U . . .
C20 C 0.35157(18) 0.91370(13) 0.68602(14) 0.0336(4) Uani 1 1 d . . . . .
H20A H 0.420658 0.929666 0.633319 0.050 Uiso 1 1 calc R U . . .
H20B H 0.381007 0.924262 0.743738 0.050 Uiso 1 1 calc R U . . .
H20C H 0.274670 0.956816 0.680982 0.050 Uiso 1 1 calc R U . . .
C21 C 0.03952(18) 0.47429(16) 0.61477(13) 0.0365(4) Uani 1 1 d . . . . .
H21A H 0.093816 0.484998 0.553507 0.055 Uiso 1 1 calc R U . . .
H21B H -0.028944 0.526853 0.623341 0.055 Uiso 1 1 calc R U . . .
H21C H 0.000310 0.409509 0.619661 0.055 Uiso 1 1 calc R U . . .
C22 C 0.27713(18) 0.38177(14) 0.68168(16) 0.0390(4) Uani 1 1 d . . . . .
H22A H 0.331819 0.381387 0.728852 0.059 Uiso 1 1 calc R U . . .
H22B H 0.329153 0.397882 0.620485 0.059 Uiso 1 1 calc R U . . .
H22C H 0.241511 0.316059 0.682939 0.059 Uiso 1 1 calc R U . . .
C23 C 0.04173(18) 0.44123(15) 0.82124(12) 0.0353(4) Uani 1 1 d . . . . .
H23A H -0.040724 0.480031 0.828942 0.053 Uiso 1 1 calc R U . . .
H23B H 0.088685 0.454532 0.870299 0.053 Uiso 1 1 calc R U . . .
H23C H 0.024934 0.370251 0.824913 0.053 Uiso 1 1 calc R U . . .
C24 C 0.68837(16) 0.63854(13) 0.60194(15) 0.0359(4) Uani 1 1 d . . . . .
H24A H 0.654071 0.600228 0.558706 0.054 Uiso 1 1 calc R U . . .
H24B H 0.682504 0.600241 0.661721 0.054 Uiso 1 1 calc R U . . .
H24C H 0.779179 0.652288 0.577018 0.054 Uiso 1 1 calc R U . . .
C25 C 0.61081(18) 0.83106(13) 0.50271(12) 0.0315(4) Uani 1 1 d . . . . .
H25A H 0.565499 0.896181 0.510039 0.047 Uiso 1 1 calc R U . . .
H25B H 0.573836 0.794777 0.459371 0.047 Uiso 1 1 calc R U . . .
H25C H 0.703015 0.840131 0.478556 0.047 Uiso 1 1 calc R U . . .
C26 C 0.66126(18) 0.82565(15) 0.70249(13) 0.0354(4) Uani 1 1 d . . . . .
H26A H 0.653632 0.785439 0.761371 0.053 Uiso 1 1 calc R U . . .
H26B H 0.613770 0.889584 0.712476 0.053 Uiso 1 1 calc R U . . .
H26C H 0.752808 0.837132 0.677958 0.053 Uiso 1 1 calc R U . . .
P3 P 0.44571(8) 0.99060(6) 1.05687(6) 0.02277(16) Uani 0.5 1 d D . P A -1
Si5 Si 0.23579(8) 1.12124(6) 0.97956(6) 0.02287(17) Uani 0.5 1 d D . P A -1
Si6 Si 0.67478(9) 0.86274(7) 1.11194(6) 0.02465(18) Uani 0.5 1 d D . P A -1
C27 C 0.4070(12) 1.0651(15) 0.9638(11) 0.0212(18) Uani 0.5 1 d D . P A -1
C28 C 0.4944(3) 1.0728(2) 0.8779(2) 0.0238(6) Uani 0.5 1 d . . P A -1
C29 C 0.6176(3) 1.0244(2) 0.8671(2) 0.0246(6) Uani 0.5 1 d . . P A -1
H29 H 0.670877 1.034295 0.807879 0.030 Uiso 0.5 1 calc R U P A -1
C30 C 0.6705(3) 0.9646(2) 0.9311(2) 0.0259(6) Uani 0.5 1 d . . P A -1
C31 C 0.6055(13) 0.9476(15) 1.0231(11) 0.0222(18) Uani 0.5 1 d D . P A -1
C32 C 0.4614(19) 1.1419(12) 0.7956(11) 0.034(2) Uani 0.5 1 d . . P A -1
H32A H 0.502233 1.205597 0.794269 0.052 Uiso 0.5 1 calc R U P A -1
H32B H 0.367222 1.153264 0.803103 0.052 Uiso 0.5 1 calc R U P A -1
H32C H 0.493779 1.110525 0.737558 0.052 Uiso 0.5 1 calc R U P A -1
C33 C 0.8102(6) 0.9246(6) 0.8976(5) 0.0329(12) Uani 0.5 1 d . . P A -1
H33A H 0.868753 0.979953 0.886117 0.049 Uiso 0.5 1 calc R U P A -1
H33B H 0.814224 0.891362 0.840293 0.049 Uiso 0.5 1 calc R U P A -1
H33C H 0.836363 0.877052 0.945166 0.049 Uiso 0.5 1 calc R U P A -1
C34 C 0.1483(12) 1.0849(14) 0.8879(8) 0.037(2) Uani 0.5 1 d . . P A -1
H34A H 0.055029 1.098142 0.907278 0.056 Uiso 0.5 1 calc R U P A -1
H34B H 0.165396 1.013884 0.878929 0.056 Uiso 0.5 1 calc R U P A -1
H34C H 0.178945 1.123603 0.829719 0.056 Uiso 0.5 1 calc R U P A -1
C35 C 0.2409(5) 1.2604(3) 0.9766(3) 0.0369(8) Uani 0.5 1 d . . P A -1
H35A H 0.152598 1.289773 0.982691 0.055 Uiso 0.5 1 calc R U P A -1
H35B H 0.292456 1.285194 0.917714 0.055 Uiso 0.5 1 calc R U P A -1
H35C H 0.280375 1.278809 1.027854 0.055 Uiso 0.5 1 calc R U P A -1
C36 C 0.1469(6) 1.0786(6) 1.0944(5) 0.0320(12) Uani 0.5 1 d . . P A -1
H36A H 0.191406 1.098804 1.142456 0.048 Uiso 0.5 1 calc R U P A -1
H36B H 0.143385 1.005992 1.098581 0.048 Uiso 0.5 1 calc R U P A -1
H36C H 0.058619 1.108301 1.103390 0.048 Uiso 0.5 1 calc R U P A -1
C37 C 0.8272(11) 0.9176(13) 1.1331(8) 0.0360(19) Uani 0.5 1 d . . P A -1
H37A H 0.885866 0.930429 1.073919 0.054 Uiso 0.5 1 calc R U P A -1
H37B H 0.869996 0.870796 1.173243 0.054 Uiso 0.5 1 calc R U P A -1
H37C H 0.804903 0.980146 1.163095 0.054 Uiso 0.5 1 calc R U P A -1
C38 C 0.7108(5) 0.7332(3) 1.0731(3) 0.0398(9) Uani 0.5 1 d . . P A -1
H38A H 0.629701 0.703122 1.068530 0.060 Uiso 0.5 1 calc R U P A -1
H38B H 0.753510 0.693140 1.118092 0.060 Uiso 0.5 1 calc R U P A -1
H38C H 0.767954 0.735717 1.012448 0.060 Uiso 0.5 1 calc R U P A -1
C39 C 0.5538(18) 0.8578(12) 1.2210(11) 0.035(2) Uani 0.5 1 d . . P A -1
H39A H 0.538155 0.924533 1.243725 0.052 Uiso 0.5 1 calc R U P A -1
H39B H 0.586806 0.812746 1.267540 0.052 Uiso 0.5 1 calc R U P A -1
H39C H 0.472535 0.833586 1.209379 0.052 Uiso 0.5 1 calc R U P A -1


_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
P1 C1 1.7410(15) . ?
P1 C5 1.7397(14) . ?
Si1 C1 1.8961(15) . ?
Si1 C8 1.8731(18) . ?
Si1 C9 1.869(2) . ?
Si1 C10 1.864(2) . ?
Si2 C5 1.8904(15) . ?
Si2 C11 1.864(2) . ?
Si2 C12 1.8766(18) . ?
Si2 C13 1.8703(19) . ?
C1 C2 1.406(2) . ?
C2 C3 1.398(2) . ?
C2 C6 1.511(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(2) . ?
C4 C5 1.408(2) . ?
C4 C7 1.512(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
P2 C14 1.7405(15) . ?
P2 C18 1.7380(16) . ?
Si3 C14 1.8919(16) . ?
Si3 C21 1.8711(18) . ?
Si3 C22 1.8707(19) . ?
Si3 C23 1.8680(18) . ?
Si4 C18 1.8921(15) . ?
Si4 C24 1.8695(18) . ?
Si4 C25 1.8766(18) . ?
Si4 C26 1.8697(18) . ?
C14 C15 1.412(2) . ?
C15 C16 1.388(2) . ?
C15 C19 1.520(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.398(2) . ?
C17 C18 1.411(2) . ?
C17 C20 1.512(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
P3 C27 1.733(11) . ?
P3 C31 1.741(12) . ?
Si5 C27 1.895(11) . ?
Si5 C34 1.876(14) . ?
Si5 C35 1.880(4) . ?
Si5 C36 1.843(8) . ?
Si6 C31 1.893(11) . ?
Si6 C37 1.889(14) . ?
Si6 C38 1.880(4) . ?
Si6 C39 1.856(19) . ?
C27 C28 1.420(13) . ?
C28 C29 1.405(4) . ?
C28 C32 1.551(14) . ?
C29 H29 0.9500 . ?
C29 C30 1.370(5) . ?
C30 C31 1.409(13) . ?
C30 C33 1.541(7) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 P1 C1 105.81(7) . . ?
C8 Si1 C1 112.25(8) . . ?
C9 Si1 C1 111.98(8) . . ?
C9 Si1 C8 108.92(8) . . ?
C10 Si1 C1 109.24(8) . . ?
C10 Si1 C8 106.66(11) . . ?
C10 Si1 C9 107.54(12) . . ?
C11 Si2 C5 110.10(8) . . ?
C11 Si2 C12 107.81(11) . . ?
C11 Si2 C13 107.11(11) . . ?
C12 Si2 C5 110.30(8) . . ?
C13 Si2 C5 112.00(8) . . ?
C13 Si2 C12 109.40(9) . . ?
P1 C1 Si1 115.34(8) . . ?
C2 C1 P1 121.31(11) . . ?
C2 C1 Si1 123.35(11) . . ?
C1 C2 C6 121.54(14) . . ?
C3 C2 C1 122.47(13) . . ?
C3 C2 C6 115.99(14) . . ?
C2 C3 H3 116.7 . . ?
C4 C3 C2 126.69(14) . . ?
C4 C3 H3 116.7 . . ?
C3 C4 C5 122.26(13) . . ?
C3 C4 C7 116.04(13) . . ?
C5 C4 C7 121.70(13) . . ?
P1 C5 Si2 115.66(8) . . ?
C4 C5 P1 121.47(11) . . ?
C4 C5 Si2 122.81(10) . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
Si1 C8 H8A 109.5 . . ?
Si1 C8 H8B 109.5 . . ?
Si1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
Si1 C9 H9A 109.5 . . ?
Si1 C9 H9B 109.5 . . ?
Si1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
Si1 C10 H10A 109.5 . . ?
Si1 C10 H10B 109.5 . . ?
Si1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
Si2 C11 H11A 109.5 . . ?
Si2 C11 H11B 109.5 . . ?
Si2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
Si2 C12 H12A 109.5 . . ?
Si2 C12 H12B 109.5 . . ?
Si2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Si2 C13 H13A 109.5 . . ?
Si2 C13 H13B 109.5 . . ?
Si2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C18 P2 C14 106.20(7) . . ?
C21 Si3 C14 110.05(8) . . ?
C22 Si3 C14 109.23(8) . . ?
C22 Si3 C21 107.78(9) . . ?
C23 Si3 C14 112.60(8) . . ?
C23 Si3 C21 109.04(9) . . ?
C23 Si3 C22 108.00(10) . . ?
C24 Si4 C18 109.41(7) . . ?
C24 Si4 C25 107.92(9) . . ?
C24 Si4 C26 106.74(9) . . ?
C25 Si4 C18 109.90(7) . . ?
C26 Si4 C18 112.08(7) . . ?
C26 Si4 C25 110.65(9) . . ?
P2 C14 Si3 115.25(8) . . ?
C15 C14 P2 120.77(12) . . ?
C15 C14 Si3 123.94(12) . . ?
C14 C15 C19 120.65(15) . . ?
C16 C15 C14 122.81(14) . . ?
C16 C15 C19 116.53(14) . . ?
C15 C16 H16 116.6 . . ?
C15 C16 C17 126.73(14) . . ?
C17 C16 H16 116.6 . . ?
C16 C17 C18 122.32(15) . . ?
C16 C17 C20 116.53(14) . . ?
C18 C17 C20 121.13(14) . . ?
P2 C18 Si4 115.28(8) . . ?
C17 C18 P2 121.16(12) . . ?
C17 C18 Si4 123.53(12) . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
Si3 C21 H21A 109.5 . . ?
Si3 C21 H21B 109.5 . . ?
Si3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Si3 C22 H22A 109.5 . . ?
Si3 C22 H22B 109.5 . . ?
Si3 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
Si3 C23 H23A 109.5 . . ?
Si3 C23 H23B 109.5 . . ?
Si3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
Si4 C24 H24A 109.5 . . ?
Si4 C24 H24B 109.5 . . ?
Si4 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
Si4 C25 H25A 109.5 . . ?
Si4 C25 H25B 109.5 . . ?
Si4 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
Si4 C26 H26A 109.5 . . ?
Si4 C26 H26B 109.5 . . ?
Si4 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C27 P3 C31 106.2(6) . . ?
C34 Si5 C27 111.5(8) . . ?
C34 Si5 C35 110.1(6) . . ?
C35 Si5 C27 109.3(7) . . ?
C36 Si5 C27 109.1(4) . . ?
C36 Si5 C34 109.4(5) . . ?
C36 Si5 C35 107.4(3) . . ?
C37 Si6 C31 108.4(8) . . ?
C38 Si6 C31 111.9(8) . . ?
C38 Si6 C37 110.3(5) . . ?
C39 Si6 C31 108.1(6) . . ?
C39 Si6 C37 109.2(6) . . ?
C39 Si6 C38 108.9(5) . . ?
P3 C27 Si5 115.9(6) . . ?
C28 C27 P3 121.1(7) . . ?
C28 C27 Si5 122.6(7) . . ?
C27 C28 C32 121.0(9) . . ?
C29 C28 C27 121.1(5) . . ?
C29 C28 C32 117.8(8) . . ?
C28 C29 H29 115.9 . . ?
C30 C29 C28 128.2(3) . . ?
C30 C29 H29 115.9 . . ?
C29 C30 C31 122.1(5) . . ?
C29 C30 C33 115.2(4) . . ?
C31 C30 C33 122.5(6) . . ?
P3 C31 Si6 115.7(6) . . ?
C30 C31 P3 120.8(8) . . ?
C30 C31 Si6 122.8(8) . . ?
C28 C32 H32A 109.5 . . ?
C28 C32 H32B 109.5 . . ?
C28 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
Si5 C34 H34A 109.5 . . ?
Si5 C34 H34B 109.5 . . ?
Si5 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
Si5 C35 H35A 109.5 . . ?
Si5 C35 H35B 109.5 . . ?
Si5 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
Si5 C36 H36A 109.5 . . ?
Si5 C36 H36B 109.5 . . ?
Si5 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
Si6 C37 H37A 109.5 . . ?
Si6 C37 H37B 109.5 . . ?
Si6 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
Si6 C38 H38A 109.5 . . ?
Si6 C38 H38B 109.5 . . ?
Si6 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
Si6 C39 H39A 109.5 . . ?
Si6 C39 H39B 109.5 . . ?
Si6 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C1 C2 C3 -0.3(2) . . . . ?
P1 C1 C2 C6 178.81(14) . . . . ?
Si1 C1 C2 C3 178.76(12) . . . . ?
Si1 C1 C2 C6 -2.1(2) . . . . ?
C1 P1 C5 Si2 176.69(8) . . . . ?
C1 P1 C5 C4 -0.41(15) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C2 C3 C4 C7 179.43(15) . . . . ?
C3 C4 C5 P1 0.6(2) . . . . ?
C3 C4 C5 Si2 -176.30(12) . . . . ?
C5 P1 C1 Si1 -178.88(8) . . . . ?
C5 P1 C1 C2 0.28(15) . . . . ?
C6 C2 C3 C4 -178.69(16) . . . . ?
C7 C4 C5 P1 -179.48(12) . . . . ?
C7 C4 C5 Si2 3.6(2) . . . . ?
C8 Si1 C1 P1 -122.20(10) . . . . ?
C8 Si1 C1 C2 58.65(16) . . . . ?
C9 Si1 C1 P1 114.91(11) . . . . ?
C9 Si1 C1 C2 -64.23(16) . . . . ?
C10 Si1 C1 P1 -4.12(14) . . . . ?
C10 Si1 C1 C2 176.74(16) . . . . ?
C11 Si2 C5 P1 2.99(13) . . . . ?
C11 Si2 C5 C4 -179.95(14) . . . . ?
C12 Si2 C5 P1 -115.86(10) . . . . ?
C12 Si2 C5 C4 61.20(15) . . . . ?
C13 Si2 C5 P1 122.04(10) . . . . ?
C13 Si2 C5 C4 -60.90(15) . . . . ?
P2 C14 C15 C16 1.2(2) . . . . ?
P2 C14 C15 C19 -177.69(12) . . . . ?
Si3 C14 C15 C16 -176.51(12) . . . . ?
Si3 C14 C15 C19 4.6(2) . . . . ?
C14 P2 C18 Si4 -177.56(8) . . . . ?
C14 P2 C18 C17 0.54(14) . . . . ?
C14 C15 C16 C17 -0.8(3) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C15 C16 C17 C20 -177.81(15) . . . . ?
C16 C17 C18 P2 -0.3(2) . . . . ?
C16 C17 C18 Si4 177.68(12) . . . . ?
C18 P2 C14 Si3 176.90(8) . . . . ?
C18 P2 C14 C15 -0.97(14) . . . . ?
C19 C15 C16 C17 178.08(16) . . . . ?
C20 C17 C18 P2 177.79(12) . . . . ?
C20 C17 C18 Si4 -4.3(2) . . . . ?
C21 Si3 C14 P2 -111.49(10) . . . . ?
C21 Si3 C14 C15 66.30(15) . . . . ?
C22 Si3 C14 P2 6.64(12) . . . . ?
C22 Si3 C14 C15 -175.56(13) . . . . ?
C23 Si3 C14 P2 126.64(9) . . . . ?
C23 Si3 C14 C15 -55.57(15) . . . . ?
C24 Si4 C18 P2 -6.45(12) . . . . ?
C24 Si4 C18 C17 175.50(13) . . . . ?
C25 Si4 C18 P2 111.88(9) . . . . ?
C25 Si4 C18 C17 -66.18(14) . . . . ?
C26 Si4 C18 P2 -124.65(10) . . . . ?
C26 Si4 C18 C17 57.30(15) . . . . ?
P3 C27 C28 C29 -3(2) . . . . ?
P3 C27 C28 C32 -178.2(12) . . . . ?
Si5 C27 C28 C29 -175.5(10) . . . . ?
Si5 C27 C28 C32 10(2) . . . . ?
C27 P3 C31 Si6 -179.7(2) . . . . ?
C27 P3 C31 C30 -8(3) . . . . ?
C27 C28 C29 C30 1.2(13) . . . . ?
C28 C29 C30 C31 -3.5(13) . . . . ?
C28 C29 C30 C33 -178.6(4) . . . . ?
C29 C30 C31 P3 7(2) . . . . ?
C29 C30 C31 Si6 178.4(10) . . . . ?
C31 P3 C27 Si5 178.9(2) . . . . ?
C31 P3 C27 C28 6(3) . . . . ?
C32 C28 C29 C30 176.3(7) . . . . ?
C33 C30 C31 P3 -177.8(10) . . . . ?
C33 C30 C31 Si6 -7(2) . . . . ?
C34 Si5 C27 P3 -122.2(13) . . . . ?
C34 Si5 C27 C28 50(2) . . . . ?
C35 Si5 C27 P3 115.8(12) . . . . ?
C35 Si5 C27 C28 -71.6(19) . . . . ?
C36 Si5 C27 P3 -1.4(16) . . . . ?
C36 Si5 C27 C28 171.3(15) . . . . ?
C37 Si6 C31 P3 -124.2(12) . . . . ?
C37 Si6 C31 C30 64.5(19) . . . . ?
C38 Si6 C31 P3 113.9(13) . . . . ?
C38 Si6 C31 C30 -57.4(19) . . . . ?
C39 Si6 C31 P3 -5.9(17) . . . . ?
C39 Si6 C31 C30 -177.3(16) . . . . ?

_olex2_submission_original_sample_id 'NTC 043'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ntc_046_1
_database_code_depnum_ccdc_archive 'CCDC 2176809'
loop_
_audit_author_name
_audit_author_address
'Nathan Coles'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2022-07-17 deposited with the CCDC.	2022-11-03 downloaded from the CCDC.
;
_audit_creation_date             2020-11-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
N.T.Coles@fu-berlin.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H25 F6 P Si2'
_chemical_formula_sum            'C17 H25 F6 P Si2'
_chemical_formula_weight         430.52
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   13.9601(6)
_cell_length_b                   7.9856(3)
_cell_length_c                   19.8245(9)
_cell_angle_alpha                90
_cell_angle_beta                 103.593(2)
_cell_angle_gamma                90
_cell_volume                     2148.13(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9863
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.87
_shelx_estimated_absorpt_T_max   0.910
_shelx_estimated_absorpt_T_min   0.825
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.9991
_exptl_absorpt_correction_T_min  0.8612
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0971 before and 0.0632 after correction.
The Ratio of minimum to maximum transmission is 0.8620.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4.00 5.00 1.00 0.2840
2.00 -2.00 1.00 0.2610
1.00 -3.00 -5.00 0.2810
-2.00 -1.00 -9.00 0.1630
2.00 1.00 9.00 0.1000
6.00 1.00 -1.00 0.1160
6.00 -1.00 -4.00 0.1950
-3.00 2.00 4.00 0.2360
-6.00 -1.00 1.00 0.1670
-4.00 -5.00 -5.00 0.2680

_exptl_crystal_size_max          0.691
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.334
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            73161
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.549
_diffrn_reflns_theta_min         2.761
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5490
_reflns_number_total             6576
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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         0.988
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         6576
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.091
_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)+(0.0261P)²+3.0126P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1073
_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:
 C3(H3)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C),
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C)
;
_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
P1 P 0.27832(3) 0.58453(5) 0.61156(2) 0.01659(9) Uani 1 1 d . . . . .
Si1 Si 0.17711(3) 0.51241(6) 0.73729(2) 0.01715(10) Uani 1 1 d . . . . .
Si2 Si 0.50288(3) 0.51544(6) 0.63295(2) 0.01908(10) Uani 1 1 d . . . . .
F1 F 0.11480(13) 0.80694(19) 0.51372(9) 0.0547(5) Uani 1 1 d . . . . .
F2 F 0.24604(11) 0.80807(18) 0.47889(9) 0.0515(4) Uani 1 1 d . . . . .
F3 F 0.11931(15) 0.69211(19) 0.41752(8) 0.0653(6) Uani 1 1 d . . . . .
F4 F 0.10953(16) 0.17352(19) 0.43017(8) 0.0731(6) Uani 1 1 d . . . . .
F5 F 0.02803(9) 0.4010(2) 0.42068(7) 0.0459(4) Uani 1 1 d . . . . .
F6 F 0.15668(10) 0.3845(2) 0.38035(6) 0.0419(3) Uani 1 1 d . . . . .
C1 C 0.20532(12) 0.4405(2) 0.65379(8) 0.0177(3) Uani 1 1 d . . . . .
C2 C 0.18723(12) 0.2914(2) 0.62206(9) 0.0193(3) Uani 1 1 d . . . . .
C3 C 0.22543(12) 0.2630(2) 0.55597(9) 0.0190(3) Uani 1 1 d . . . . .
H3 H 0.206920 0.148588 0.536742 0.023 Uiso 1 1 calc R U . . .
C4 C 0.33862(12) 0.2819(2) 0.57685(9) 0.0190(3) Uani 1 1 d . . . . .
C5 C 0.37487(12) 0.4299(2) 0.60251(8) 0.0176(3) Uani 1 1 d . . . . .
C6 C 0.20156(12) 0.5547(2) 0.52234(9) 0.0185(3) Uani 1 1 d . . . . .
C7 C 0.18181(12) 0.3959(2) 0.50278(9) 0.0192(3) Uani 1 1 d . . . . .
C8 C 0.13653(16) 0.1426(2) 0.64398(11) 0.0297(4) Uani 1 1 d . . . . .
H8A H 0.121934 0.165009 0.689120 0.045 Uiso 1 1 calc R U . . .
H8B H 0.179565 0.044362 0.647680 0.045 Uiso 1 1 calc R U . . .
H8C H 0.074960 0.120994 0.609454 0.045 Uiso 1 1 calc R U . . .
C9 C 0.39377(14) 0.1248(2) 0.56827(10) 0.0253(4) Uani 1 1 d . . . . .
H9A H 0.374345 0.034736 0.595874 0.038 Uiso 1 1 calc R U . . .
H9B H 0.464764 0.144968 0.584104 0.038 Uiso 1 1 calc R U . . .
H9C H 0.378181 0.092313 0.519232 0.038 Uiso 1 1 calc R U . . .
C10 C 0.16878(13) 0.7120(2) 0.48230(9) 0.0231(3) Uani 1 1 d . . . . .
C11 C 0.11947(16) 0.3388(3) 0.43361(10) 0.0286(4) Uani 1 1 d . . . . .
C12 C 0.05634(13) 0.4353(3) 0.75022(10) 0.0255(4) Uani 1 1 d . . . . .
H12A H 0.004955 0.454384 0.707847 0.038 Uiso 1 1 calc R U . . .
H12B H 0.039640 0.495750 0.788921 0.038 Uiso 1 1 calc R U . . .
H12C H 0.061092 0.315184 0.760682 0.038 Uiso 1 1 calc R U . . .
C13 C 0.17386(13) 0.7454(2) 0.73592(9) 0.0225(3) Uani 1 1 d . . . . .
H13A H 0.237159 0.788510 0.730117 0.034 Uiso 1 1 calc R U . . .
H13B H 0.161754 0.786826 0.779705 0.034 Uiso 1 1 calc R U . . .
H13C H 0.120957 0.783527 0.697223 0.034 Uiso 1 1 calc R U . . .
C14 C 0.27831(13) 0.4349(2) 0.81000(9) 0.0246(3) Uani 1 1 d . . . . .
H14A H 0.275975 0.312374 0.811837 0.037 Uiso 1 1 calc R U . . .
H14B H 0.269879 0.481422 0.853980 0.037 Uiso 1 1 calc R U . . .
H14C H 0.342090 0.470319 0.802263 0.037 Uiso 1 1 calc R U . . .
C15 C 0.51297(14) 0.6953(2) 0.57461(10) 0.0246(4) Uani 1 1 d . . . . .
H15A H 0.517699 0.652664 0.529146 0.037 Uiso 1 1 calc R U . . .
H15B H 0.571999 0.760858 0.595016 0.037 Uiso 1 1 calc R U . . .
H15C H 0.454488 0.766548 0.569085 0.037 Uiso 1 1 calc R U . . .
C16 C 0.60425(14) 0.3652(3) 0.63072(11) 0.0298(4) Uani 1 1 d . . . . .
H16A H 0.601269 0.271118 0.661918 0.045 Uiso 1 1 calc R U . . .
H16B H 0.667901 0.422077 0.645764 0.045 Uiso 1 1 calc R U . . .
H16C H 0.596890 0.323290 0.583310 0.045 Uiso 1 1 calc R U . . .
C17 C 0.51656(15) 0.5900(3) 0.72442(10) 0.0299(4) Uani 1 1 d . . . . .
H17A H 0.464263 0.670667 0.726050 0.045 Uiso 1 1 calc R U . . .
H17B H 0.580937 0.643859 0.740615 0.045 Uiso 1 1 calc R U . . .
H17C H 0.511620 0.494329 0.754391 0.045 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C1 1.8613(16) . ?
P1 C5 1.8673(17) . ?
P1 C6 1.8554(17) . ?
Si1 C1 1.8791(17) . ?
Si1 C12 1.8684(18) . ?
Si1 C13 1.8611(19) . ?
Si1 C14 1.8707(18) . ?
Si2 C5 1.8755(17) . ?
Si2 C15 1.8698(19) . ?
Si2 C16 1.864(2) . ?
Si2 C17 1.8751(19) . ?
F1 C10 1.324(2) . ?
F2 C10 1.338(2) . ?
F3 C10 1.317(2) . ?
F4 C11 1.327(2) . ?
F5 C11 1.337(2) . ?
F6 C11 1.333(2) . ?
C1 C2 1.342(2) . ?
C2 C3 1.543(2) . ?
C2 C8 1.499(2) . ?
C3 H3 1.0000 . ?
C3 C4 1.544(2) . ?
C3 C7 1.519(2) . ?
C4 C5 1.338(2) . ?
C4 C9 1.502(2) . ?
C6 C7 1.336(2) . ?
C6 C10 1.499(2) . ?
C7 C11 1.511(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 C5 96.80(7) . . ?
C6 P1 C1 95.44(8) . . ?
C6 P1 C5 95.26(7) . . ?
C12 Si1 C1 113.75(8) . . ?
C12 Si1 C14 109.12(8) . . ?
C13 Si1 C1 107.60(8) . . ?
C13 Si1 C12 108.17(9) . . ?
C13 Si1 C14 110.69(9) . . ?
C14 Si1 C1 107.51(8) . . ?
C15 Si2 C5 106.57(8) . . ?
C15 Si2 C17 110.43(9) . . ?
C16 Si2 C5 115.42(9) . . ?
C16 Si2 C15 108.17(9) . . ?
C16 Si2 C17 108.78(10) . . ?
C17 Si2 C5 107.43(8) . . ?
P1 C1 Si1 117.23(9) . . ?
C2 C1 P1 113.57(12) . . ?
C2 C1 Si1 128.95(13) . . ?
C1 C2 C3 117.64(15) . . ?
C1 C2 C8 128.09(16) . . ?
C8 C2 C3 114.23(15) . . ?
C2 C3 H3 110.4 . . ?
C2 C3 C4 107.10(13) . . ?
C4 C3 H3 110.4 . . ?
C7 C3 C2 108.94(14) . . ?
C7 C3 H3 110.4 . . ?
C7 C3 C4 109.61(14) . . ?
C5 C4 C3 117.40(15) . . ?
C5 C4 C9 128.49(16) . . ?
C9 C4 C3 114.03(15) . . ?
P1 C5 Si2 112.51(9) . . ?
C4 C5 P1 113.80(12) . . ?
C4 C5 Si2 133.68(13) . . ?
C7 C6 P1 115.62(13) . . ?
C7 C6 C10 128.70(16) . . ?
C10 C6 P1 115.67(12) . . ?
C6 C7 C3 116.11(15) . . ?
C6 C7 C11 125.82(16) . . ?
C11 C7 C3 118.07(15) . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
F1 C10 F2 104.47(17) . . ?
F1 C10 C6 111.57(15) . . ?
F2 C10 C6 110.98(15) . . ?
F3 C10 F1 107.57(18) . . ?
F3 C10 F2 105.31(17) . . ?
F3 C10 C6 116.13(16) . . ?
F4 C11 F5 106.01(19) . . ?
F4 C11 F6 106.68(19) . . ?
F4 C11 C7 112.18(16) . . ?
F5 C11 C7 112.47(16) . . ?
F6 C11 F5 106.18(16) . . ?
F6 C11 C7 112.81(17) . . ?
Si1 C12 H12A 109.5 . . ?
Si1 C12 H12B 109.5 . . ?
Si1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Si1 C13 H13A 109.5 . . ?
Si1 C13 H13B 109.5 . . ?
Si1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Si1 C14 H14A 109.5 . . ?
Si1 C14 H14B 109.5 . . ?
Si1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
Si2 C15 H15A 109.5 . . ?
Si2 C15 H15B 109.5 . . ?
Si2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Si2 C16 H16A 109.5 . . ?
Si2 C16 H16B 109.5 . . ?
Si2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Si2 C17 H17A 109.5 . . ?
Si2 C17 H17B 109.5 . . ?
Si2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C1 C2 C3 -1.7(2) . . . . ?
P1 C1 C2 C8 175.95(16) . . . . ?
P1 C6 C7 C3 -0.4(2) . . . . ?
P1 C6 C7 C11 178.67(15) . . . . ?
P1 C6 C10 F1 -60.2(2) . . . . ?
P1 C6 C10 F2 55.84(19) . . . . ?
P1 C6 C10 F3 176.04(15) . . . . ?
Si1 C1 C2 C3 -175.75(12) . . . . ?
Si1 C1 C2 C8 1.9(3) . . . . ?
C1 P1 C5 Si2 -132.19(9) . . . . ?
C1 P1 C5 C4 46.90(14) . . . . ?
C1 P1 C6 C7 -48.52(15) . . . . ?
C1 P1 C6 C10 130.61(13) . . . . ?
C1 C2 C3 C4 60.50(19) . . . . ?
C1 C2 C3 C7 -58.0(2) . . . . ?
C2 C3 C4 C5 -60.89(19) . . . . ?
C2 C3 C4 C9 116.38(16) . . . . ?
C2 C3 C7 C6 58.78(19) . . . . ?
C2 C3 C7 C11 -120.36(17) . . . . ?
C3 C4 C5 P1 2.5(2) . . . . ?
C3 C4 C5 Si2 -178.61(13) . . . . ?
C3 C7 C11 F4 1.7(3) . . . . ?
C3 C7 C11 F5 121.13(18) . . . . ?
C3 C7 C11 F6 -118.79(18) . . . . ?
C4 C3 C7 C6 -58.1(2) . . . . ?
C4 C3 C7 C11 122.75(17) . . . . ?
C5 P1 C1 Si1 127.54(9) . . . . ?
C5 P1 C1 C2 -47.21(14) . . . . ?
C5 P1 C6 C7 48.84(14) . . . . ?
C5 P1 C6 C10 -132.03(13) . . . . ?
C6 P1 C1 Si1 -136.48(10) . . . . ?
C6 P1 C1 C2 48.76(14) . . . . ?
C6 P1 C5 Si2 131.68(9) . . . . ?
C6 P1 C5 C4 -49.23(14) . . . . ?
C6 C7 C11 F4 -177.3(2) . . . . ?
C6 C7 C11 F5 -57.9(3) . . . . ?
C6 C7 C11 F6 62.2(3) . . . . ?
C7 C3 C4 C5 57.1(2) . . . . ?
C7 C3 C4 C9 -125.58(16) . . . . ?
C7 C6 C10 F1 118.8(2) . . . . ?
C7 C6 C10 F2 -125.2(2) . . . . ?
C7 C6 C10 F3 -5.0(3) . . . . ?
C8 C2 C3 C4 -117.51(16) . . . . ?
C8 C2 C3 C7 124.01(16) . . . . ?
C9 C4 C5 P1 -174.27(15) . . . . ?
C9 C4 C5 Si2 4.6(3) . . . . ?
C10 C6 C7 C3 -179.39(16) . . . . ?
C10 C6 C7 C11 -0.3(3) . . . . ?
C12 Si1 C1 P1 147.76(9) . . . . ?
C12 Si1 C1 C2 -38.42(19) . . . . ?
C13 Si1 C1 P1 27.96(12) . . . . ?
C13 Si1 C1 C2 -158.22(16) . . . . ?
C14 Si1 C1 P1 -91.30(11) . . . . ?
C14 Si1 C1 C2 82.51(17) . . . . ?
C15 Si2 C5 P1 -63.38(11) . . . . ?
C15 Si2 C5 C4 117.77(18) . . . . ?
C16 Si2 C5 P1 176.50(9) . . . . ?
C16 Si2 C5 C4 -2.3(2) . . . . ?
C17 Si2 C5 P1 54.98(12) . . . . ?
C17 Si2 C5 C4 -123.87(18) . . . . ?

_olex2_submission_original_sample_id NTC-046-1
_olex2_submission_special_instructions 'No special instructions were received'
