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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2169890'
loop_
_audit_author_name
_audit_author_address
'Aline Lacoudre'
;Institut des Sciences Moleculaires (ISM), Universite de Bordeaux
France
;
_audit_update_record             
;
2022-05-02 deposited with the CCDC.	2022-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'UVX1 Phenol'
_chemical_name_common            'Compound 6'
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H34 N2 O2 Si'
_chemical_formula_sum            'C21 H34 N2 O2 Si'
_chemical_formula_weight         374.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.6666(12)
_cell_length_b                   14.7352(16)
_cell_length_c                   13.3183(14)
_cell_angle_alpha                90
_cell_angle_beta                 105.646(2)
_cell_angle_gamma                90
_cell_volume                     2204.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3055
_cell_measurement_theta_min      2.063
_cell_measurement_theta_max      26.402

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.129
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.123
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6857
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS v2012/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tude'
_diffrn_measurement_device_type  'Bruker APEX Duo'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            30764
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.063
_diffrn_reflns_theta_max         26.402
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4533
_reflns_number_gt                3055
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 20133.10-0 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.34A (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT v8.34A (Bruker AXS Inc.)'
_computing_structure_solution    
'SUPERFLIP(Palatinus & Chapuis, 2007) EDMA(Palatinus et al., 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0588P)²+1.6166P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4533
_refine_ls_number_parameters     244
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1573
_refine_ls_wR_factor_gt          0.1355
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.84817(6) 0.41078(4) 0.19797(5) 0.03532(19) Uani 1 1 d . . . . .
O1 O 0.33164(18) 0.41665(18) 0.2079(2) 0.0771(7) Uani 1 1 d . . . . .
H1O H 0.299962 0.367004 0.192684 0.116 Uiso 1 1 calc R U . . .
O2 O 1.19686(18) 0.26285(19) 0.1705(2) 0.0796(7) Uani 1 1 d . . . . .
H2O H 1.125449 0.274171 0.156017 0.119 Uiso 1 1 calc R U . . .
N1 N 0.79645(17) 0.32558(15) -0.00976(17) 0.0435(5) Uani 1 1 d . . . . .
N2 N 0.9546(2) 0.27111(17) 0.10460(19) 0.0573(7) Uani 1 1 d . . . . .
C12 C 0.8785(3) 0.4052(3) 0.4154(2) 0.0703(9) Uani 1 1 d . . . . .
H12A H 0.914204 0.377819 0.481898 0.105 Uiso 1 1 calc R U . . .
H12B H 0.793433 0.400396 0.399953 0.105 Uiso 1 1 calc R U . . .
H12C H 0.900745 0.468022 0.417348 0.105 Uiso 1 1 calc R U . . .
C6 C 0.4931(2) 0.3394(2) 0.1616(2) 0.0540(7) Uani 1 1 d . . . . .
H6 H 0.446403 0.288308 0.139148 0.065 Uiso 1 1 calc R U . . .
C15 C 0.8671(2) 0.33218(17) 0.0907(2) 0.0405(6) Uani 1 1 d . . . . .
C4 C 0.6847(2) 0.41573(17) 0.1898(2) 0.0410(6) Uani 1 1 d . . . . .
C7 C 0.9138(2) 0.52546(18) 0.1757(2) 0.0461(6) Uani 1 1 d . . . . .
C18 C 0.6939(2) 0.3802(2) -0.0634(2) 0.0585(8) Uani 1 1 d . . . . .
H18A H 0.665687 0.413848 -0.013072 0.088 Uiso 1 1 calc R U . . .
H18B H 0.631739 0.341198 -0.102176 0.088 Uiso 1 1 calc R U . . .
H18C H 0.716801 0.421620 -0.110186 0.088 Uiso 1 1 calc R U . . .
C1 C 0.4457(2) 0.4135(2) 0.1993(2) 0.0538(7) Uani 1 1 d . . . . .
C16 C 0.9384(3) 0.2249(2) 0.0117(3) 0.0688(10) Uani 1 1 d . . . . .
C5 C 0.6105(2) 0.34113(19) 0.1573(2) 0.0492(7) Uani 1 1 d . . . . .
H5 H 0.640929 0.290490 0.131666 0.059 Uiso 1 1 calc R U . . .
C9 C 0.9332(3) 0.5912(2) 0.2686(3) 0.0678(9) Uani 1 1 d . . . . .
H9A H 0.986785 0.564289 0.328833 0.102 Uiso 1 1 calc R U . . .
H9B H 0.858306 0.603348 0.282904 0.102 Uiso 1 1 calc R U . . .
H9C H 0.966512 0.646915 0.251891 0.102 Uiso 1 1 calc R U . . .
C11 C 0.9217(2) 0.35625(19) 0.3308(2) 0.0471(6) Uani 1 1 d . . . . .
C2 C 0.5158(3) 0.4890(2) 0.2306(2) 0.0592(8) Uani 1 1 d . . . . .
H2 H 0.484446 0.539713 0.255261 0.071 Uiso 1 1 calc R U . . .
C3 C 0.6325(2) 0.4898(2) 0.2255(2) 0.0520(7) Uani 1 1 d . . . . .
H3 H 0.678002 0.541726 0.246752 0.062 Uiso 1 1 calc R U . . .
C13 C 1.0581(3) 0.3600(2) 0.3616(2) 0.0638(8) Uani 1 1 d . . . . .
H13A H 1.083668 0.422109 0.366829 0.096 Uiso 1 1 calc R U . . .
H13B H 1.087102 0.329638 0.309505 0.096 Uiso 1 1 calc R U . . .
H13C H 1.088851 0.330430 0.427614 0.096 Uiso 1 1 calc R U . . .
C17 C 0.8423(3) 0.2585(2) -0.0583(2) 0.0576(8) Uani 1 1 d . . . . .
H17 H 0.812556 0.239496 -0.127003 0.069 Uiso 1 1 calc R U . . .
C10 C 1.0358(3) 0.5108(2) 0.1537(3) 0.0657(9) Uani 1 1 d . . . . .
H10A H 1.065455 0.567786 0.136342 0.099 Uiso 1 1 calc R U . . .
H10B H 1.026996 0.469386 0.096428 0.099 Uiso 1 1 calc R U . . .
H10C H 1.090849 0.486024 0.214544 0.099 Uiso 1 1 calc R U . . .
C19 C 1.0147(4) 0.1458(4) 0.0002(4) 0.133(2) Uani 1 1 d D . . . .
H19A H 0.980165 0.092738 0.023850 0.159 Uiso 1 1 calc R U . . .
H19B H 1.004104 0.137771 -0.074062 0.159 Uiso 1 1 calc R U . . .
C21 C 1.2143(4) 0.1767(4) 0.1289(4) 0.1107(16) Uani 1 1 d D . . . .
H21A H 1.289109 0.179486 0.110298 0.133 Uiso 1 1 calc R U . . .
H21B H 1.224876 0.132928 0.185065 0.133 Uiso 1 1 calc R U . . .
C8 C 0.8317(3) 0.5725(2) 0.0794(3) 0.0646(9) Uani 1 1 d . . . . .
H8A H 0.754178 0.580871 0.090030 0.097 Uiso 1 1 calc R U . . .
H8B H 0.825225 0.535478 0.018830 0.097 Uiso 1 1 calc R U . . .
H8C H 0.864505 0.630497 0.069407 0.097 Uiso 1 1 calc R U . . .
C14 C 0.8824(3) 0.2565(2) 0.3292(3) 0.0717(10) Uani 1 1 d . . . . .
H14A H 0.911411 0.223589 0.278831 0.107 Uiso 1 1 calc R U . . .
H14B H 0.797068 0.253424 0.310663 0.107 Uiso 1 1 calc R U . . .
H14C H 0.914216 0.230280 0.396945 0.107 Uiso 1 1 calc R U . . .
C20 C 1.1308(4) 0.1416(3) 0.0445(6) 0.153(3) Uani 1 1 d D . . . .
H20A H 1.163580 0.157257 -0.012899 0.184 Uiso 1 1 calc R U . . .
H20B H 1.143969 0.076752 0.053993 0.184 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
Si1 C4 1.882(3) . ?
Si1 C15 1.898(3) . ?
Si1 C7 1.911(3) . ?
Si1 C11 1.922(3) . ?
O1 C1 1.367(3) . ?
O2 C21 1.422(5) . ?
N1 C17 1.367(3) . ?
N1 C15 1.372(3) . ?
N1 C18 1.459(3) . ?
N2 C15 1.336(3) . ?
N2 C16 1.379(4) . ?
C12 C11 1.533(4) . ?
C6 C1 1.379(4) . ?
C6 C5 1.387(4) . ?
C4 C5 1.394(4) . ?
C4 C3 1.395(4) . ?
C7 C9 1.538(4) . ?
C7 C8 1.544(4) . ?
C7 C10 1.544(4) . ?
C1 C2 1.377(4) . ?
C16 C17 1.344(4) . ?
C16 C19 1.500(5) . ?
C11 C13 1.534(4) . ?
C11 C14 1.538(4) . ?
C2 C3 1.381(4) . ?
C19 C20 1.324(6) . ?
C21 C20 1.375(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
C4 Si1 C15 107.56(11) . . ?
C4 Si1 C7 113.52(12) . . ?
C15 Si1 C7 106.87(12) . . ?
C4 Si1 C11 105.25(12) . . ?
C15 Si1 C11 108.94(12) . . ?
C7 Si1 C11 114.48(12) . . ?
C17 N1 C15 107.7(2) . . ?
C17 N1 C18 122.8(2) . . ?
C15 N1 C18 129.5(2) . . ?
C15 N2 C16 107.0(2) . . ?
C1 C6 C5 119.9(3) . . ?
N2 C15 N1 108.9(2) . . ?
N2 C15 Si1 123.08(19) . . ?
N1 C15 Si1 128.04(18) . . ?
C5 C4 C3 115.5(2) . . ?
C5 C4 Si1 121.50(19) . . ?
C3 C4 Si1 122.6(2) . . ?
C9 C7 C8 108.0(2) . . ?
C9 C7 C10 107.4(2) . . ?
C8 C7 C10 107.6(2) . . ?
C9 C7 Si1 114.2(2) . . ?
C8 C7 Si1 109.93(18) . . ?
C10 C7 Si1 109.52(19) . . ?
O1 C1 C2 117.4(3) . . ?
O1 C1 C6 123.5(3) . . ?
C2 C1 C6 119.1(2) . . ?
C17 C16 N2 109.1(3) . . ?
C17 C16 C19 128.4(3) . . ?
N2 C16 C19 122.3(3) . . ?
C6 C5 C4 122.7(3) . . ?
C12 C11 C13 108.1(2) . . ?
C12 C11 C14 107.7(3) . . ?
C13 C11 C14 108.8(2) . . ?
C12 C11 Si1 109.1(2) . . ?
C13 C11 Si1 113.8(2) . . ?
C14 C11 Si1 109.22(19) . . ?
C1 C2 C3 120.4(3) . . ?
C2 C3 C4 122.4(3) . . ?
C16 C17 N1 107.3(2) . . ?
C20 C19 C16 123.7(4) . . ?
C20 C21 O2 120.7(3) . . ?
C19 C20 C21 139.5(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
C16 N2 C15 N1 -0.4(3) . . . . ?
C16 N2 C15 Si1 178.3(2) . . . . ?
C17 N1 C15 N2 0.1(3) . . . . ?
C18 N1 C15 N2 -176.7(3) . . . . ?
C17 N1 C15 Si1 -178.5(2) . . . . ?
C18 N1 C15 Si1 4.7(4) . . . . ?
C4 Si1 C15 N2 -138.1(2) . . . . ?
C7 Si1 C15 N2 99.7(2) . . . . ?
C11 Si1 C15 N2 -24.5(3) . . . . ?
C4 Si1 C15 N1 40.4(3) . . . . ?
C7 Si1 C15 N1 -81.9(2) . . . . ?
C11 Si1 C15 N1 154.0(2) . . . . ?
C15 Si1 C4 C5 32.7(3) . . . . ?
C7 Si1 C4 C5 150.7(2) . . . . ?
C11 Si1 C4 C5 -83.3(2) . . . . ?
C15 Si1 C4 C3 -154.0(2) . . . . ?
C7 Si1 C4 C3 -36.0(3) . . . . ?
C11 Si1 C4 C3 89.9(2) . . . . ?
C5 C6 C1 O1 -178.7(3) . . . . ?
C5 C6 C1 C2 1.0(4) . . . . ?
C15 N2 C16 C17 0.6(4) . . . . ?
C15 N2 C16 C19 -175.1(4) . . . . ?
C1 C6 C5 C4 0.0(5) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
Si1 C4 C5 C6 172.6(2) . . . . ?
O1 C1 C2 C3 178.9(3) . . . . ?
C6 C1 C2 C3 -0.8(5) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C5 C4 C3 C2 1.3(4) . . . . ?
Si1 C4 C3 C2 -172.3(2) . . . . ?
N2 C16 C17 N1 -0.6(4) . . . . ?
C19 C16 C17 N1 174.9(4) . . . . ?
C15 N1 C17 C16 0.3(3) . . . . ?
C18 N1 C17 C16 177.4(3) . . . . ?
C17 C16 C19 C20 146.3(6) . . . . ?
N2 C16 C19 C20 -38.8(9) . . . . ?
C16 C19 C20 C21 25.3(14) . . . . ?
O2 C21 C20 C19 -28.0(14) . . . . ?

_refine_diff_density_max         0.403
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.047


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyle acetate/toluene'
