# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_exp_374
_database_code_depnum_ccdc_archive 'CCDC 1560336'
_audit_update_record             
;
2017-07-05 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;
_audit_creation_date             2017-04-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H22 Si'
_chemical_formula_sum            'C22 H22 Si'
_chemical_formula_weight         314.49
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 Si1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   8.8464(4)
_cell_length_b                   13.6195(6)
_cell_length_c                   30.1026(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3626.9(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    19225
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      29.6840
_cell_measurement_theta_min      4.0160
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic whiteish colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            60476
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.55
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  22.00   0.25    1.51    --   -1.00 -38.00   0.00  192
  2  ω    -11.00  16.00   0.25    1.51    --   -1.00 -82.00  60.00  108
  3  ω      8.00  35.00   0.25    1.51    --    1.40 -82.00   0.00  108
  4  ω     -8.00  33.00   0.25    1.51    --    1.40 -77.00-120.00  164
  5  ω    -25.00  35.00   0.25    1.51    --    1.40 -82.00 -60.00  240
  6  ω    -32.00  35.00   0.25    1.51    --    1.40 -82.00 120.00  268
  7  ω    -32.00   6.00   0.25    1.51    --   -1.00  19.00 -60.00  152
  8  ω     43.00  87.00   0.25    1.51    --   -1.00  19.00 -60.00  176
  9  ω    -45.00 -20.00   0.25    1.51    --    1.40 -77.00-120.00  100
 10  ω    -90.00 -16.00   0.25    1.51    --   -1.00 -69.00  10.00  296
 11  ω    -88.00 -31.00   0.25    1.51    --   -1.00 -38.00 -60.00  228
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0132093000
_diffrn_orient_matrix_UB_12      -0.0505010000
_diffrn_orient_matrix_UB_13      -0.0042663000
_diffrn_orient_matrix_UB_21      0.0483346000
_diffrn_orient_matrix_UB_22      0.0127628000
_diffrn_orient_matrix_UB_23      -0.0178672000
_diffrn_orient_matrix_UB_31      0.0626148000
_diffrn_orient_matrix_UB_32      0.0007666000
_diffrn_orient_matrix_UB_33      0.0147389000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3246
_reflns_number_total             3555
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3555
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0502P)²+1.5922P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1005
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C14(H14), C15(H15), C17(H17),
 C18(H18)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Si1 Si 0.34503(4) 0.18907(3) 0.444308(12) 0.02921(12) Uani 1 d . . .
C1 C 0.14303(14) 0.14196(9) 0.36585(4) 0.0239(3) Uani 1 d . . .
C2 C 0.17373(14) 0.14054(9) 0.41306(5) 0.0267(3) Uani 1 d . . .
C3 C 0.06501(16) 0.09797(11) 0.44016(5) 0.0350(3) Uani 1 d . . .
H3 H 0.0828 0.0963 0.4706 0.042 Uiso 1 calc . . R
C4 C -0.07144(16) 0.05703(11) 0.42406(6) 0.0393(4) Uani 1 d . . .
H4 H -0.1405 0.0295 0.4437 0.047 Uiso 1 calc . . R
C5 C -0.10093(16) 0.05816(10) 0.38000(5) 0.0353(3) Uani 1 d . . .
H5 H -0.1904 0.0310 0.3694 0.042 Uiso 1 calc . . R
C6 C 0.00364(14) 0.10052(9) 0.34973(5) 0.0286(3) Uani 1 d . . .
C7 C -0.03319(16) 0.10195(11) 0.30404(5) 0.0360(3) Uani 1 d . . .
H7 H -0.1245 0.0752 0.2946 0.043 Uiso 1 calc . . R
C8 C 0.06308(16) 0.14203(11) 0.27342(5) 0.0359(3) Uani 1 d . . .
H8 H 0.0377 0.1425 0.2434 0.043 Uiso 1 calc . . R
C9 C 0.20038(16) 0.18229(10) 0.28784(5) 0.0303(3) Uani 1 d . . .
H9 H 0.2658 0.2094 0.2670 0.036 Uiso 1 calc . . R
C10 C 0.24168(14) 0.18289(9) 0.33252(4) 0.0242(3) Uani 1 d . . .
C11 C 0.38787(15) 0.22594(10) 0.34066(4) 0.0262(3) Uani 1 d . . .
C12 C 0.51129(15) 0.26341(10) 0.33924(4) 0.0281(3) Uani 1 d . . .
C13 C 0.65806(14) 0.30870(9) 0.33658(4) 0.0262(3) Uani 1 d . . .
C14 C 0.70206(15) 0.35646(10) 0.29754(4) 0.0289(3) Uani 1 d . . .
H14 H 0.6356 0.3594 0.2736 0.035 Uiso 1 calc . . R
C15 C 0.84395(15) 0.39965(10) 0.29401(5) 0.0304(3) Uani 1 d . . .
H15 H 0.8710 0.4310 0.2677 0.037 Uiso 1 calc . . R
C16 C 0.94663(15) 0.39685(9) 0.32921(5) 0.0284(3) Uani 1 d . . .
C17 C 0.90176(16) 0.34968(10) 0.36827(5) 0.0309(3) Uani 1 d . . .
H17 H 0.9680 0.3475 0.3922 0.037 Uiso 1 calc . . R
C18 C 0.76071(16) 0.30610(10) 0.37211(4) 0.0301(3) Uani 1 d . . .
H18 H 0.7339 0.2749 0.3984 0.036 Uiso 1 calc . . R
C19 C 1.10124(17) 0.44322(11) 0.32547(6) 0.0393(3) Uani 1 d . . .
H19A H 1.1756 0.3929 0.3208 0.059 Uiso 1 calc . . GR
H19B H 1.1239 0.4782 0.3524 0.059 Uiso 1 calc . . GR
H19C H 1.1025 0.4880 0.3009 0.059 Uiso 1 calc . . GR
C20 C 0.51739(16) 0.11393(12) 0.43167(6) 0.0399(3) Uani 1 d . . .
H20A H 0.5393 0.1177 0.4005 0.060 Uiso 1 calc . . GR
H20B H 0.4994 0.0468 0.4398 0.060 Uiso 1 calc . . GR
H20C H 0.6017 0.1389 0.4483 0.060 Uiso 1 calc . . GR
C21 C 0.36526(19) 0.32576(11) 0.43844(5) 0.0406(4) Uani 1 d . . .
H21A H 0.3354 0.3452 0.4091 0.061 Uiso 1 calc . . GR
H21B H 0.4687 0.3440 0.4434 0.061 Uiso 1 calc . . GR
H21C H 0.3020 0.3579 0.4599 0.061 Uiso 1 calc . . GR
C22 C 0.3147(2) 0.17003(15) 0.50553(5) 0.0533(5) Uani 1 d . . .
H22A H 0.3972 0.1985 0.5217 0.080 Uiso 1 calc . . GR
H22B H 0.3094 0.1010 0.5118 0.080 Uiso 1 calc . . GR
H22C H 0.2218 0.2009 0.5144 0.080 Uiso 1 calc . . GR

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Si1 0.0279(2) 0.0350(2) 0.0248(2) 0.00051(14) 0.00040(14) -0.00204(15)
C1 0.0204(6) 0.0191(6) 0.0322(7) -0.0011(5) 0.0017(5) 0.0024(5)
C2 0.0234(6) 0.0253(6) 0.0315(7) 0.0002(5) 0.0041(5) 0.0015(5)
C3 0.0315(7) 0.0382(8) 0.0354(7) 0.0040(6) 0.0068(6) -0.0002(6)
C4 0.0279(7) 0.0379(8) 0.0521(9) 0.0084(7) 0.0120(6) -0.0049(6)
C5 0.0229(6) 0.0288(7) 0.0543(9) 0.0012(6) 0.0028(6) -0.0043(5)
C6 0.0224(6) 0.0224(6) 0.0409(7) -0.0016(5) 0.0000(5) 0.0007(5)
C7 0.0271(7) 0.0343(7) 0.0467(8) -0.0029(6) -0.0091(6) -0.0035(6)
C8 0.0330(7) 0.0419(8) 0.0328(7) -0.0009(6) -0.0088(6) 0.0009(6)
C9 0.0272(7) 0.0333(7) 0.0304(7) 0.0025(5) -0.0002(5) 0.0021(5)
C10 0.0211(6) 0.0226(6) 0.0290(6) -0.0004(5) 0.0004(5) 0.0024(5)
C11 0.0258(7) 0.0296(7) 0.0234(6) 0.0010(5) 0.0022(5) 0.0004(5)
C12 0.0267(7) 0.0332(7) 0.0244(6) -0.0003(5) 0.0022(5) -0.0012(5)
C13 0.0232(6) 0.0266(6) 0.0289(7) -0.0027(5) 0.0024(5) -0.0014(5)
C14 0.0269(7) 0.0327(7) 0.0270(6) -0.0006(5) -0.0008(5) -0.0011(5)
C15 0.0308(7) 0.0301(7) 0.0305(7) 0.0018(5) 0.0063(5) -0.0030(6)
C16 0.0243(6) 0.0227(6) 0.0380(7) -0.0059(5) 0.0032(5) -0.0007(5)
C17 0.0283(7) 0.0308(7) 0.0337(7) -0.0031(5) -0.0056(5) -0.0006(5)
C18 0.0307(7) 0.0319(7) 0.0276(6) 0.0022(5) 0.0002(5) -0.0025(5)
C19 0.0303(7) 0.0349(8) 0.0525(9) -0.0059(7) 0.0039(6) -0.0081(6)
C20 0.0300(7) 0.0428(8) 0.0469(9) 0.0083(7) -0.0030(6) 0.0027(6)
C21 0.0461(9) 0.0372(8) 0.0386(8) -0.0087(6) -0.0008(7) -0.0042(7)
C22 0.0550(10) 0.0763(13) 0.0287(8) 0.0032(8) -0.0006(7) -0.0132(9)

_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 C2 1.9021(14) . ?
Si1 C20 1.8753(16) . ?
Si1 C21 1.8785(16) . ?
Si1 C22 1.8804(17) . ?
C1 C2 1.4470(19) . ?
C1 C6 1.4403(18) . ?
C1 C10 1.4420(18) . ?
C2 C3 1.3879(19) . ?
C3 C4 1.415(2) . ?
C4 C5 1.352(2) . ?
C5 C6 1.4211(19) . ?
C6 C7 1.414(2) . ?
C7 C8 1.369(2) . ?
C8 C9 1.402(2) . ?
C9 C10 1.3936(18) . ?
C10 C11 1.4411(18) . ?
C11 C12 1.2059(19) . ?
C12 C13 1.4397(18) . ?
C13 C14 1.3985(19) . ?
C13 C18 1.4035(19) . ?
C14 C15 1.3903(19) . ?
C15 C16 1.396(2) . ?
C16 C17 1.397(2) . ?
C16 C19 1.5107(18) . ?
C17 C18 1.386(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 Si1 C2 110.96(7) . . ?
C20 Si1 C21 116.38(7) . . ?
C20 Si1 C22 103.87(8) . . ?
C21 Si1 C2 111.95(7) . . ?
C21 Si1 C22 104.03(8) . . ?
C22 Si1 C2 108.84(7) . . ?
C6 C1 C2 119.11(12) . . ?
C6 C1 C10 115.78(12) . . ?
C10 C1 C2 125.10(11) . . ?
C1 C2 Si1 129.09(10) . . ?
C3 C2 Si1 114.00(11) . . ?
C3 C2 C1 116.91(12) . . ?
C2 C3 C4 123.68(14) . . ?
C5 C4 C3 119.73(13) . . ?
C4 C5 C6 120.55(13) . . ?
C5 C6 C1 120.01(13) . . ?
C7 C6 C1 121.33(12) . . ?
C7 C6 C5 118.66(13) . . ?
C8 C7 C6 121.16(13) . . ?
C7 C8 C9 119.12(13) . . ?
C10 C9 C8 121.90(13) . . ?
C9 C10 C1 120.71(12) . . ?
C9 C10 C11 113.69(12) . . ?
C11 C10 C1 125.60(11) . . ?
C12 C11 C10 168.15(13) . . ?
C11 C12 C13 178.80(14) . . ?
C14 C13 C12 119.80(12) . . ?
C14 C13 C18 118.17(12) . . ?
C18 C13 C12 122.03(12) . . ?
C15 C14 C13 120.82(13) . . ?
C14 C15 C16 121.18(13) . . ?
C15 C16 C17 117.79(12) . . ?
C15 C16 C19 121.40(13) . . ?
C17 C16 C19 120.81(13) . . ?
C18 C17 C16 121.51(13) . . ?
C17 C18 C13 120.52(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.393
_oxdiff_exptl_absorpt_empirical_full_min 0.706
####################################################################### 
# 
# 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_exp_7582
_database_code_depnum_ccdc_archive 'CCDC 1560337'
_audit_update_record             
;
2017-07-05 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;
_audit_creation_date             2016-09-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H20 Si'
_chemical_formula_sum            'C21 H20 Si'
_chemical_formula_weight         300.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H20N2O3U1
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'
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 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.2864(7)
_cell_length_b                   9.5206(6)
_cell_length_c                   14.4288(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.731(6)
_cell_angle_gamma                90.00
_cell_volume                     1676.15(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5019
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      27.7130
_cell_measurement_theta_min      3.3120
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19569
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.84
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -26.00   44.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5454  -77.0000 -150.0000 70

#__ type_ start__ end____ width___ exp.time_
  2 omega  -15.00   82.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5454   38.0000   90.0000 97

#__ type_ start__ end____ width___ exp.time_
  3 omega  -52.00   23.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5454  -57.0000  120.0000 75

#__ type_ start__ end____ width___ exp.time_
  4 omega  -16.00   26.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6392  -99.0000   60.0000 42

#__ type_ start__ end____ width___ exp.time_
  5 omega  -38.00   50.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6392   38.0000  -30.0000 88

#__ type_ start__ end____ width___ exp.time_
  6 omega -102.00  -77.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6392 -178.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega  -88.00   15.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6392  -38.0000  150.0000 103
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0276611000
_diffrn_orient_matrix_UB_12      -0.0598414000
_diffrn_orient_matrix_UB_13      -0.0148932000
_diffrn_orient_matrix_UB_21      -0.0151594000
_diffrn_orient_matrix_UB_22      0.0194005000
_diffrn_orient_matrix_UB_23      -0.0471947000
_diffrn_orient_matrix_UB_31      0.0488406000
_diffrn_orient_matrix_UB_32      0.0399005000
_diffrn_orient_matrix_UB_33      0.0006576000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2605
_reflns_number_total             3304
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0415P)²+0.7241P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1069
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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:
 C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Si1 Si 0.25275(4) 0.59751(5) 0.14965(4) 0.02745(15) Uani 1 d . . .
C1 C 0.35832(14) 0.58564(18) 0.25258(12) 0.0259(4) Uani 1 d . . .
C2 C 0.37263(17) 0.6572(2) 0.33601(13) 0.0341(4) Uani 1 d . . .
H2 H 0.3206 0.7228 0.3495 0.041 Uiso 1 calc . . R
C3 C 0.46503(18) 0.6322(2) 0.40088(13) 0.0409(5) Uani 1 d . . .
H3 H 0.4730 0.6804 0.4573 0.049 Uiso 1 calc . . R
C4 C 0.54307(17) 0.5383(2) 0.38223(13) 0.0383(5) Uani 1 d . . .
H4 H 0.6037 0.5235 0.4261 0.046 Uiso 1 calc . . R
C5 C 0.53336(15) 0.46305(19) 0.29741(12) 0.0286(4) Uani 1 d . . .
C6 C 0.43945(14) 0.48637(18) 0.23299(12) 0.0244(4) Uani 1 d . . .
C7 C 0.61477(15) 0.37032(19) 0.27210(13) 0.0322(4) Uani 1 d . . .
H7 H 0.6764 0.3513 0.3141 0.039 Uiso 1 calc . . R
C8 C 0.60300(15) 0.30894(19) 0.18638(14) 0.0335(4) Uani 1 d . . .
H8 H 0.6582 0.2505 0.1698 0.040 Uiso 1 calc . . R
C9 C 0.50921(14) 0.33181(19) 0.12223(13) 0.0296(4) Uani 1 d . . .
H9 H 0.5039 0.2888 0.0640 0.036 Uiso 1 calc . . R
C10 C 0.42517(13) 0.41684(17) 0.14417(12) 0.0235(4) Uani 1 d . . .
C11 C 0.32095(13) 0.45503(18) 0.08574(12) 0.0252(4) Uani 1 d . . .
C12 C 0.28126(14) 0.39985(19) 0.00278(12) 0.0271(4) Uani 1 d . . .
C13 C 0.17719(16) 0.4542(2) -0.05157(15) 0.0449(5) Uani 1 d . . .
H13A H 0.1459 0.5258 -0.0160 0.067 Uiso 1 calc . . GR
H13B H 0.1259 0.3785 -0.0635 0.067 Uiso 1 calc . . GR
H13C H 0.1937 0.4930 -0.1097 0.067 Uiso 1 calc . . GR
C14 C 0.33101(13) 0.28283(19) -0.04661(12) 0.0252(4) Uani 1 d . . .
C15 C 0.33211(14) 0.14546(19) -0.01392(12) 0.0291(4) Uani 1 d . . .
H15 H 0.3037 0.1254 0.0416 0.035 Uiso 1 calc . . R
C16 C 0.37507(15) 0.0385(2) -0.06323(13) 0.0319(4) Uani 1 d . . .
H16 H 0.3754 -0.0529 -0.0405 0.038 Uiso 1 calc . . R
C17 C 0.41743(16) 0.0659(2) -0.14559(14) 0.0342(4) Uani 1 d . . .
H17 H 0.4465 -0.0065 -0.1783 0.041 Uiso 1 calc . . R
C18 C 0.41634(16) 0.2019(2) -0.17914(14) 0.0362(5) Uani 1 d . . .
H18 H 0.4450 0.2214 -0.2346 0.043 Uiso 1 calc . . R
C19 C 0.37274(15) 0.3086(2) -0.13031(13) 0.0314(4) Uani 1 d . . .
H19 H 0.3713 0.3996 -0.1539 0.038 Uiso 1 calc . . R
C20 C 0.25384(19) 0.7724(2) 0.09267(15) 0.0443(5) Uani 1 d . . .
H20A H 0.3279 0.7984 0.0857 0.066 Uiso 1 calc . . GR
H20B H 0.2225 0.8410 0.1305 0.066 Uiso 1 calc . . GR
H20C H 0.2117 0.7683 0.0324 0.066 Uiso 1 calc . . GR
C21 C 0.11333(16) 0.5566(3) 0.18091(17) 0.0480(6) Uani 1 d . . .
H21A H 0.0623 0.5530 0.1252 0.072 Uiso 1 calc . . GR
H21B H 0.0912 0.6283 0.2216 0.072 Uiso 1 calc . . GR
H21C H 0.1146 0.4674 0.2120 0.072 Uiso 1 calc . . GR

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Si1 0.0250(3) 0.0244(3) 0.0335(3) -0.0001(2) 0.0060(2) 0.0046(2)
C1 0.0292(9) 0.0229(9) 0.0271(9) 0.0036(7) 0.0099(8) -0.0022(7)
C2 0.0447(11) 0.0311(10) 0.0297(10) -0.0001(8) 0.0172(9) -0.0008(9)
C3 0.0573(14) 0.0433(12) 0.0228(9) -0.0031(8) 0.0077(9) -0.0064(10)
C4 0.0460(12) 0.0421(12) 0.0253(10) 0.0041(9) -0.0015(9) -0.0028(10)
C5 0.0325(10) 0.0266(10) 0.0259(9) 0.0074(7) 0.0006(8) -0.0041(8)
C6 0.0276(9) 0.0205(9) 0.0260(9) 0.0052(7) 0.0062(7) -0.0029(7)
C7 0.0287(10) 0.0284(10) 0.0373(11) 0.0075(8) -0.0063(8) 0.0010(8)
C8 0.0261(9) 0.0247(10) 0.0482(12) -0.0023(9) -0.0022(8) 0.0027(8)
C9 0.0246(9) 0.0253(10) 0.0379(10) -0.0080(8) -0.0012(8) 0.0001(7)
C10 0.0218(8) 0.0197(9) 0.0289(9) 0.0006(7) 0.0027(7) -0.0021(7)
C11 0.0212(8) 0.0239(9) 0.0307(9) -0.0001(7) 0.0039(7) 0.0005(7)
C12 0.0222(9) 0.0271(9) 0.0315(10) 0.0003(8) 0.0006(7) 0.0000(7)
C13 0.0346(11) 0.0496(13) 0.0471(12) -0.0113(10) -0.0089(10) 0.0122(10)
C14 0.0188(8) 0.0280(10) 0.0275(9) -0.0043(7) -0.0023(7) -0.0026(7)
C15 0.0299(10) 0.0329(10) 0.0244(9) 0.0028(8) 0.0032(8) 0.0003(8)
C16 0.0353(10) 0.0247(10) 0.0361(10) 0.0020(8) 0.0062(8) 0.0001(8)
C17 0.0357(10) 0.0283(10) 0.0408(11) -0.0058(8) 0.0129(9) -0.0006(8)
C18 0.0397(11) 0.0350(11) 0.0369(11) -0.0024(9) 0.0177(9) -0.0079(9)
C19 0.0331(10) 0.0249(10) 0.0368(10) 0.0018(8) 0.0071(8) -0.0056(8)
C20 0.0582(14) 0.0314(11) 0.0425(12) 0.0060(9) 0.0030(10) 0.0091(10)
C21 0.0284(11) 0.0523(14) 0.0653(15) -0.0061(11) 0.0137(10) 0.0046(10)

_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 C1 1.8572(19) . ?
Si1 C11 1.8904(17) . ?
Si1 C20 1.858(2) . ?
Si1 C21 1.863(2) . ?
C1 C2 1.377(3) . ?
C1 C6 1.426(2) . ?
C2 C3 1.404(3) . ?
C3 C4 1.361(3) . ?
C4 C5 1.411(3) . ?
C5 C6 1.412(2) . ?
C5 C7 1.414(3) . ?
C6 C10 1.435(2) . ?
C7 C8 1.360(3) . ?
C8 C9 1.408(3) . ?
C9 C10 1.378(2) . ?
C10 C11 1.493(2) . ?
C11 C12 1.345(2) . ?
C12 C13 1.511(3) . ?
C12 C14 1.492(2) . ?
C14 C15 1.390(3) . ?
C14 C19 1.388(2) . ?
C15 C16 1.382(3) . ?
C16 C17 1.377(3) . ?
C17 C18 1.382(3) . ?
C18 C19 1.380(3) . ?

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 Si1 C11 92.21(8) . . ?
C1 Si1 C20 111.58(9) . . ?
C1 Si1 C21 111.68(9) . . ?
C20 Si1 C11 113.62(9) . . ?
C20 Si1 C21 110.44(11) . . ?
C21 Si1 C11 116.15(9) . . ?
C2 C1 Si1 132.43(15) . . ?
C2 C1 C6 118.75(17) . . ?
C6 C1 Si1 108.71(13) . . ?
C1 C2 C3 120.61(18) . . ?
C4 C3 C2 120.86(18) . . ?
C3 C4 C5 121.02(19) . . ?
C4 C5 C6 118.07(17) . . ?
C4 C5 C7 123.41(17) . . ?
C6 C5 C7 118.46(16) . . ?
C1 C6 C10 117.89(16) . . ?
C5 C6 C1 120.68(16) . . ?
C5 C6 C10 121.36(16) . . ?
C8 C7 C5 120.00(17) . . ?
C7 C8 C9 121.53(17) . . ?
C10 C9 C8 121.16(17) . . ?
C6 C10 C11 113.52(15) . . ?
C9 C10 C6 117.38(16) . . ?
C9 C10 C11 129.01(16) . . ?
C10 C11 Si1 107.40(12) . . ?
C12 C11 Si1 125.38(13) . . ?
C12 C11 C10 127.21(16) . . ?
C11 C12 C13 121.63(17) . . ?
C11 C12 C14 126.20(16) . . ?
C14 C12 C13 112.16(15) . . ?
C15 C14 C12 121.93(15) . . ?
C19 C14 C12 119.82(16) . . ?
C19 C14 C15 118.16(16) . . ?
C16 C15 C14 120.51(16) . . ?
C17 C16 C15 120.72(17) . . ?
C16 C17 C18 119.38(17) . . ?
C19 C18 C17 119.97(17) . . ?
C18 C19 C14 121.25(17) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
