# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_test3_a
_database_code_depnum_ccdc_archive 'CCDC 1862618'
_audit_update_record             
;
2018-08-17 deposited with the CCDC.
2018-10-04 downloaded from the CCDC.
;

_audit_creation_date             2018-04-03T09:45:34-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
        1-(phenylethynyl)2-(trimethylsilyl)-1H-indol
;
_chemical_name_common            'phenylethynyl trimethylsilyl indol'
_chemical_formula_moiety         'C38 H38 N2 Si2'
_chemical_formula_sum            'C38 H38 N2 Si2'
_chemical_formula_weight         578.88
_chemical_melting_point          332K
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1


#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.0160(4)
_cell_length_b                   11.9919(4)
_cell_length_c                   13.0752(5)
_cell_angle_alpha                89.5180(10)
_cell_angle_beta                 75.5500(10)
_cell_angle_gamma                80.3100(10)
_cell_volume                     1647.74(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    9886
_cell_measurement_theta_min      2.362
_cell_measurement_theta_max      27.905

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_special_details           
;
 none
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_absorpt_correction_T_min  0.9451
_exptl_absorpt_correction_T_max  0.982

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus tube'
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_reflns_av_R_equivalents  0.023
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_number            26553
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         27.93
_diffrn_reflns_theta_full        27.93
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             7884
_reflns_number_gt                6774
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact GbR'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2σ(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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0421P)²+0.5950P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         7884
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0946
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.039

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.05905(12) -0.31345(13) 0.34829(10) 0.0319(3) Uani 1 1 d . . .
H1 H 1.1319 -0.3512 0.2978 0.038 Uiso 1 1 calc R . .
C2 C 1.03102(12) -0.19526(14) 0.35114(10) 0.0338(3) Uani 1 1 d . . .
H2 H 1.086 -0.1543 0.3035 0.041 Uiso 1 1 calc R . .
C3 C 0.92469(12) -0.13671(12) 0.42210(10) 0.0290(3) Uani 1 1 d . . .
H3 H 0.9044 -0.0564 0.4238 0.035 Uiso 1 1 calc R . .
C4 C 0.84921(11) -0.20137(11) 0.49068(9) 0.0222(2) Uani 1 1 d . . .
C5 C 0.87609(11) -0.31943(11) 0.49166(9) 0.0222(2) Uani 1 1 d . . .
C6 C 0.98332(12) -0.37651(12) 0.41715(10) 0.0276(3) Uani 1 1 d . . .
H6 H 1.0032 -0.4568 0.4143 0.033 Uiso 1 1 calc R . .
C8 C 0.69488(11) -0.26019(10) 0.62205(9) 0.0205(2) Uani 1 1 d . . .
C9 C 0.77838(11) -0.35399(10) 0.57494(9) 0.0218(2) Uani 1 1 d . . .
H9 H 0.7728 -0.4299 0.5941 0.026 Uiso 1 1 calc R . .
C10 C 0.67931(11) -0.05608(11) 0.58562(9) 0.0231(2) Uani 1 1 d . . .
C11 C 0.63254(12) 0.04163(11) 0.59320(9) 0.0243(2) Uani 1 1 d . . .
C13 C 0.65177(12) 0.24246(11) 0.58208(9) 0.0243(2) Uani 1 1 d . . .
H13 H 0.7415 0.2219 0.5693 0.029 Uiso 1 1 calc R . .
C14 C 0.59709(13) 0.35498(11) 0.58356(10) 0.0284(3) Uani 1 1 d . . .
H14 H 0.6495 0.4115 0.571 0.034 Uiso 1 1 calc R . .
C15 C 0.46583(13) 0.38592(11) 0.60333(10) 0.0292(3) Uani 1 1 d . . .
H15 H 0.4285 0.4635 0.6044 0.035 Uiso 1 1 calc R . .
C16 C 0.38969(12) 0.30345(12) 0.62144(10) 0.0289(3) Uani 1 1 d . . .
H16 H 0.2999 0.3247 0.6357 0.035 Uiso 1 1 calc R . .
C17 C 0.57532(11) 0.15870(10) 0.59938(9) 0.0217(2) Uani 1 1 d . . .
C18 C 0.44317(12) 0.19057(11) 0.61894(9) 0.0259(3) Uani 1 1 d . . .
H18 H 0.3903 0.1344 0.6305 0.031 Uiso 1 1 calc R . .
C19 C 0.54246(15) -0.39288(12) 0.78568(12) 0.0368(3) Uani 1 1 d . . .
H19A H 0.5355 -0.4435 0.7297 0.055 Uiso 1 1 calc R . .
H19B H 0.4683 -0.3904 0.846 0.055 Uiso 1 1 calc R . .
H19C H 0.6202 -0.421 0.8082 0.055 Uiso 1 1 calc R . .
C20 C 0.40760(12) -0.19264(13) 0.68424(11) 0.0326(3) Uani 1 1 d . . .
H20A H 0.402 -0.2445 0.6287 0.049 Uiso 1 1 calc R . .
H20B H 0.416 -0.1179 0.6552 0.049 Uiso 1 1 calc R . .
H20C H 0.3304 -0.1862 0.7422 0.049 Uiso 1 1 calc R . .
C21 C 0.56169(12) -0.15148(11) 0.84018(10) 0.0257(3) Uani 1 1 d . . .
H21A H 0.6365 -0.1818 0.866 0.039 Uiso 1 1 calc R . .
H21B H 0.485 -0.1449 0.8986 0.039 Uiso 1 1 calc R . .
H21C H 0.5704 -0.0766 0.8116 0.039 Uiso 1 1 calc R . .
C22 C 0.29649(13) 0.84438(14) 1.13220(10) 0.0359(3) Uani 1 1 d . . .
H22 H 0.324 0.8912 1.177 0.043 Uiso 1 1 calc R . .
C23 C 0.33274(13) 0.72677(14) 1.13240(10) 0.0355(3) Uani 1 1 d . . .
H23 H 0.3843 0.6954 1.1774 0.043 Uiso 1 1 calc R . .
C24 C 0.29499(12) 0.65528(13) 1.06840(10) 0.0304(3) Uani 1 1 d . . .
H24 H 0.3194 0.5754 1.0682 0.036 Uiso 1 1 calc R . .
C25 C 0.21935(11) 0.70620(11) 1.00422(9) 0.0242(2) Uani 1 1 d . . .
C26 C 0.18127(11) 0.82326(11) 1.00219(9) 0.0247(3) Uani 1 1 d . . .
C27 C 0.22138(13) 0.89368(13) 1.06797(10) 0.0311(3) Uani 1 1 d . . .
H27 H 0.1974 0.9736 1.0683 0.037 Uiso 1 1 calc R . .
C29 C 0.09960(11) 0.74086(10) 0.88332(9) 0.0218(2) Uani 1 1 d . . .
C30 C 0.10607(12) 0.84245(11) 0.92637(9) 0.0242(2) Uani 1 1 d . . .
H30 H 0.067 0.9144 0.9089 0.029 Uiso 1 1 calc R . .
C31 C 0.18495(11) 0.54302(11) 0.91358(9) 0.0247(2) Uani 1 1 d . . .
C32 C 0.20101(12) 0.44278(11) 0.90086(10) 0.0256(3) Uani 1 1 d . . .
C33 C 0.22166(11) 0.32219(10) 0.88732(9) 0.0232(2) Uani 1 1 d . . .
C34 C 0.32767(12) 0.25735(11) 0.91224(10) 0.0259(3) Uani 1 1 d . . .
H34 H 0.3852 0.2936 0.9378 0.031 Uiso 1 1 calc R . .
C35 C 0.34911(13) 0.14077(11) 0.89991(10) 0.0289(3) Uani 1 1 d . . .
H35 H 0.421 0.0971 0.9174 0.035 Uiso 1 1 calc R . .
C36 C 0.26603(13) 0.08734(11) 0.86211(10) 0.0293(3) Uani 1 1 d . . .
H36 H 0.2815 0.0073 0.8528 0.035 Uiso 1 1 calc R . .
C37 C 0.16025(13) 0.15112(12) 0.83795(11) 0.0306(3) Uani 1 1 d . . .
H37 H 0.1031 0.1144 0.8124 0.037 Uiso 1 1 calc R . .
C38 C 0.13731(12) 0.26800(11) 0.85073(10) 0.0282(3) Uani 1 1 d . . .
H38 H 0.0643 0.3111 0.8346 0.034 Uiso 1 1 calc R . .
C40 C -0.04162(19) 0.85007(13) 0.73209(13) 0.0467(4) Uani 1 1 d . . .
H40A H -0.1067 0.8905 0.7913 0.07 Uiso 1 1 calc R . .
H40B H -0.0799 0.8394 0.6735 0.07 Uiso 1 1 calc R . .
H40C H 0.0269 0.8943 0.7087 0.07 Uiso 1 1 calc R . .
C41 C 0.14778(13) 0.63170(13) 0.66384(11) 0.0335(3) Uani 1 1 d . . .
H41A H 0.1819 0.5579 0.6875 0.05 Uiso 1 1 calc R . .
H41B H 0.2167 0.6754 0.6402 0.05 Uiso 1 1 calc R . .
H41C H 0.1099 0.6205 0.6052 0.05 Uiso 1 1 calc R . .
C42 C -0.10152(12) 0.62284(13) 0.82444(10) 0.0315(3) Uani 1 1 d . . .
H42A H -0.0631 0.5497 0.8462 0.047 Uiso 1 1 calc R . .
H42B H -0.1426 0.6105 0.7681 0.047 Uiso 1 1 calc R . .
H42C H -0.1651 0.6624 0.885 0.047 Uiso 1 1 calc R . .
N7 N 0.73804(9) -0.16554(9) 0.56930(8) 0.0214(2) Uani 1 1 d . . .
N28 N 0.16912(10) 0.65618(9) 0.93208(8) 0.0231(2) Uani 1 1 d . . .
Si18 Si 0.54872(3) -0.24833(3) 0.73471(2) 0.02071(8) Uani 1 1 d . . .
Si39 Si 0.02418(3) 0.71003(3) 0.77512(3) 0.02245(9) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.3800(19) . ?
C1 C2 1.398(2) . ?
C2 C3 1.3848(19) . ?
C3 C4 1.3892(17) . ?
C4 N7 1.3939(15) . ?
C4 C5 1.3974(18) . ?
C5 C6 1.4063(17) . ?
C5 C9 1.4401(16) . ?
C8 C9 1.3679(16) . ?
C8 N7 1.4124(15) . ?
C8 Si18 1.8776(12) . ?
C10 C11 1.1923(18) . ?
C10 N7 1.3554(16) . ?
C11 C17 1.4329(17) . ?
C13 C14 1.3801(18) . ?
C13 C17 1.3983(17) . ?
C14 C15 1.3892(19) . ?
C15 C16 1.383(2) . ?
C16 C18 1.3795(19) . ?
C17 C18 1.3996(17) . ?
C19 Si18 1.8578(14) . ?
C20 Si18 1.8583(14) . ?
C21 Si18 1.8580(12) . ?
C22 C27 1.383(2) . ?
C22 C23 1.400(2) . ?
C23 C24 1.383(2) . ?
C24 C25 1.3930(18) . ?
C25 N28 1.3919(16) . ?
C25 C26 1.3979(18) . ?
C26 C27 1.4055(18) . ?
C26 C30 1.4367(17) . ?
C29 C30 1.3663(17) . ?
C29 N28 1.4124(15) . ?
C29 Si39 1.8780(12) . ?
C31 C32 1.1921(18) . ?
C31 N28 1.3547(16) . ?
C32 C33 1.4309(18) . ?
C33 C38 1.3946(18) . ?
C33 C34 1.3980(17) . ?
C34 C35 1.3820(18) . ?
C35 C36 1.3861(19) . ?
C36 C37 1.3865(19) . ?
C37 C38 1.3855(19) . ?
C40 Si39 1.8548(15) . ?
C41 Si39 1.8594(13) . ?
C42 Si39 1.8593(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 121.47(12) . . ?
C3 C2 C1 121.26(12) . . ?
C2 C3 C4 116.58(13) . . ?
C3 C4 N7 128.89(12) . . ?
C3 C4 C5 123.63(12) . . ?
N7 C4 C5 107.47(10) . . ?
C4 C5 C6 118.38(11) . . ?
C4 C5 C9 106.80(10) . . ?
C6 C5 C9 134.81(12) . . ?
C1 C6 C5 118.63(13) . . ?
C9 C8 N7 106.84(10) . . ?
C9 C8 Si18 129.98(9) . . ?
N7 C8 Si18 123.18(9) . . ?
C8 C9 C5 109.20(11) . . ?
C11 C10 N7 175.46(13) . . ?
C10 C11 C17 178.29(13) . . ?
C14 C13 C17 120.13(11) . . ?
C13 C14 C15 120.31(12) . . ?
C16 C15 C14 119.77(12) . . ?
C18 C16 C15 120.52(12) . . ?
C13 C17 C18 119.19(11) . . ?
C13 C17 C11 120.07(11) . . ?
C18 C17 C11 120.70(11) . . ?
C16 C18 C17 120.07(12) . . ?
C27 C22 C23 121.25(13) . . ?
C24 C23 C22 121.37(13) . . ?
C23 C24 C25 116.69(14) . . ?
N28 C25 C24 129.18(12) . . ?
N28 C25 C26 107.40(11) . . ?
C24 C25 C26 123.41(12) . . ?
C25 C26 C27 118.56(12) . . ?
C25 C26 C30 106.86(11) . . ?
C27 C26 C30 134.58(13) . . ?
C22 C27 C26 118.71(14) . . ?
C30 C29 N28 106.82(10) . . ?
C30 C29 Si39 129.69(10) . . ?
N28 C29 Si39 123.41(9) . . ?
C29 C30 C26 109.24(11) . . ?
C32 C31 N28 177.26(13) . . ?
C31 C32 C33 178.80(14) . . ?
C38 C33 C34 119.34(12) . . ?
C38 C33 C32 121.25(11) . . ?
C34 C33 C32 119.41(11) . . ?
C35 C34 C33 120.28(12) . . ?
C34 C35 C36 120.20(12) . . ?
C35 C36 C37 119.79(12) . . ?
C38 C37 C36 120.50(12) . . ?
C37 C38 C33 119.88(12) . . ?
C10 N7 C4 123.37(10) . . ?
C10 N7 C8 126.84(10) . . ?
C4 N7 C8 109.68(10) . . ?
C31 N28 C25 124.15(11) . . ?
C31 N28 C29 126.16(10) . . ?
C25 N28 C29 109.68(10) . . ?
C19 Si18 C21 109.86(7) . . ?
C19 Si18 C20 111.73(7) . . ?
C21 Si18 C20 110.36(6) . . ?
C19 Si18 C8 106.67(6) . . ?
C21 Si18 C8 109.59(6) . . ?
C20 Si18 C8 108.53(6) . . ?
C40 Si39 C42 111.91(8) . . ?
C40 Si39 C41 110.19(8) . . ?
C42 Si39 C41 109.13(6) . . ?
C40 Si39 C29 105.69(6) . . ?
C42 Si39 C29 110.50(6) . . ?
C41 Si39 C29 109.37(6) . . ?

# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH3OH/CH2Cl2'
