# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2009 data_global _journal_coden_Cambridge 440 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Philippe Gerbier' 'Laurent Aubouy' 'Lionel Hirsch' 'Nolwenn Huby' 'van der Lee, Arie' _publ_contact_author_name 'Philippe Gerbier' _publ_contact_author_email GERBIER@UNIV-MONTP2.FR _publ_section_title ; Molecular engineering to improve the balance of charge carrier in single-layer silole-based OLEDs. ; # Attachment 'gerb102.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 725599' _audit_creation_date 08-05-28 _audit_creation_method CRYSTALS_ver_12.85 _chemical_name_systematic ? _chemical_melting_point ? #looking for refcif # Check this file using the IUCr facility at: # http://checkcif.iucr.org/ # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. The dichloromethane was found to be heavily disordered. Two carbon positions and seven chlore position were found. The total site occupancy of the carbon positions were strongly restrained to 1 and that of the chlore positions to 2. Restraints were also put on the Uiso parameters of carbon and chlore in order to have them approximately equal. No attempts were made to place the proton sites for C53 and C54. The occupancy of C60 which was refined to 0.0503(5) was fixed to 0.500 in order to avoid problems with another two- fold axis related C60 at a too short distance. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # Hand-made tables can be put in the cif. The number of columns # is set in the loop header. # The contants of each column can either be a piece of text # without any spaces (eg a number) or other text enclosed in " " # Remove the leading # in the following example #geom_extra_table_head_A #; #Table 2. #Molecular parameters deviating most from MOGUL averages #; # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 #_geom_extra_tableA_col_4 # #Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" #N5-C6-C4 129 124 "7 (\%)" #C3-O10-C2 105 109 "2 (\%)" #C6-O7 1.25 1.22 ".02 (\%A)" # # End of 'script/refcif-b.dat' #end of refcif _cell_length_a 13.8694(8) _cell_length_b 14.3213(8) _cell_length_c 26.3741(14) _cell_angle_alpha 90 _cell_angle_beta 98.256(4) _cell_angle_gamma 90 _cell_volume 5184.4(5) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z -x+1/2,-y+1/2,-z -x,y,-z+1/2 x,-y,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Si 0.0817 0.0704 6.2915 2.4386 3.0353 32.3337 1.9891 0.6785 1.5410 81.6937 1.1407 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328 2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 _chemical_formula_sum 'C56 H44 Br2 Cl4 Si2' _chemical_formula_moiety 'C56 H44 Br2 Cl4 Si2' _chemical_compound_source ? _chemical_formula_weight 1074.78 _cell_measurement_reflns_used 10077 _cell_measurement_theta_min 2.7005 _cell_measurement_theta_max 32.4427 _cell_measurement_temperature 173 _exptl_crystal_description ? _exptl_crystal_colour 'yellow transparant' _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_max 0.35 _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 2184.027 _exptl_absorpt_coefficient_mu 1.852 # Sheldrick geometric approximatio 0.63 0.69 _exptl_absorpt_correction_T_min 0.91726 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_detector_area_resol_mean 8.4205 _diffrn_measurement_device 'Oxford Diffraction XCALIBUR' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_sigmaI/netI 0.047 _diffrn_measurement_method \w _diffrn_orient_matrix_UB_11 0.0126722596 _diffrn_orient_matrix_UB_12 -0.0166904149 _diffrn_orient_matrix_UB_13 0.0254310468 _diffrn_orient_matrix_UB_21 -0.0284439785 _diffrn_orient_matrix_UB_22 0.0359184683 _diffrn_orient_matrix_UB_23 0.0090506787 _diffrn_orient_matrix_UB_31 -0.0412597059 _diffrn_orient_matrix_UB_32 -0.0297923648 _diffrn_orient_matrix_UB_33 -0.0033308947 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -54.00 61.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 30.0000 -79.0000 0.0000 0.0000 0.0000 115 #__ type_ start__ end____ width___ exp.time_ 2 omega -54.00 61.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 30.0000 -79.0000 90.0000 0.0000 0.0000 115 #__ type_ start__ end____ width___ exp.time_ 3 omega -54.00 61.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 30.0000 -79.0000 180.0000 0.0000 0.0000 115 #__ type_ start__ end____ width___ exp.time_ 4 omega -54.00 61.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 30.0000 -79.0000 270.0000 0.0000 0.0000 115 #__ type_ start__ end____ width___ exp.time_ 5 omega -111.00 10.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -25.0000 -80.0000 100.0000 0.0000 0.0000 121 #__ type_ start__ end____ width___ exp.time_ 6 omega -116.00 71.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -25.0000 -10.0000 180.0000 0.0000 0.0000 187 #__ type_ start__ end____ width___ exp.time_ 7 omega -110.00 12.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -25.0000 -80.0000 0.0000 0.0000 0.0000 122 ; # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2006)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ' 30 frames' _diffrn_standards_number ' 2 frames' _diffrn_standards_decay_% 0 _diffrn_ambient_temperature 173 _diffrn_reflns_number 50775 _reflns_number_total 8532 _diffrn_reflns_av_R_equivalents 0.059 # Number of reflections with Friedels Law is 8532 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 9257 _diffrn_reflns_theta_min 2.707 _diffrn_reflns_theta_max 32.549 _diffrn_measured_fraction_theta_max 0.905 _diffrn_reflns_theta_full 29.945 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _reflns_limit_h_min -19 _reflns_limit_h_max 19 _reflns_limit_k_min 0 _reflns_limit_k_max 21 _reflns_limit_l_min 0 _reflns_limit_l_max 39 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.61 _refine_diff_density_max 0.63 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>2.0\s(I) _refine_ls_number_reflns 3634 _refine_ls_number_restraints 2 _refine_ls_number_parameters 306 _oxford_refine_ls_R_factor_ref 0.0391 _refine_ls_wR_factor_ref 0.0383 _refine_ls_goodness_of_fit_ref 1.1260 _refine_ls_shift/su_max 0.000882 # The values computed from all data _oxford_reflns_number_all 8532 _refine_ls_R_factor_all 0.1198 _refine_ls_wR_factor_all 0.0720 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3634 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_gt 0.0383 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 5.02 -5.94 3.60 -1.40 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Oxford Diffraction, (2002). CrysAlis RED. Oxford Diffraction, (2002). Xcalibur User Manual. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens Br1 Br 0.80760(3) 0.12255(3) 0.666100(13) 0.0465 1.0000 Uani . . . . . . . C2 C 0.7809(2) 0.0820(2) 0.59703(11) 0.0306 1.0000 Uani . . . . . . . C3 C 0.8023(2) -0.0090(2) 0.58532(11) 0.0341 1.0000 Uani . . . . . . . C4 C 0.7818(2) -0.0402(2) 0.53521(11) 0.0303 1.0000 Uani . . . . . . . C5 C 0.7387(2) 0.0182(2) 0.49583(10) 0.0247 1.0000 Uani . . . . . . . C6 C 0.7105(2) -0.0139(2) 0.44238(10) 0.0253 1.0000 Uani . . . . . . . Si7 Si 0.59740(6) 0.02186(6) 0.39880(3) 0.0257 1.0000 Uani . . . . . . . C8 C 0.6207(2) -0.0643(2) 0.34881(10) 0.0255 1.0000 Uani . . . . . . . C9 C 0.7063(2) -0.1079(2) 0.36525(10) 0.0261 1.0000 Uani . . . . . . . C10 C 0.7542(2) -0.0811(2) 0.41775(10) 0.0240 1.0000 Uani . . . . . . . C11 C 0.8430(2) -0.1327(2) 0.44051(10) 0.0253 1.0000 Uani . . . . . . . C12 C 0.8348(3) -0.2258(2) 0.45370(12) 0.0358 1.0000 Uani . . . . . . . C13 C 0.9133(3) -0.2728(3) 0.48000(14) 0.0482 1.0000 Uani . . . . . . . C14 C 1.0008(3) -0.2292(3) 0.49136(14) 0.0523 1.0000 Uani . . . . . . . C15 C 1.0119(2) -0.1384(3) 0.47686(14) 0.0489 1.0000 Uani . . . . . . . C16 C 0.9329(2) -0.0890(3) 0.45167(12) 0.0358 1.0000 Uani . . . . . . . H17 H 0.9392 -0.0267 0.4431 0.0550 1.0000 Uiso R . . . . . . H18 H 1.0702 -0.1094 0.4836 0.0550 1.0000 Uiso R . . . . . . H19 H 1.0526 -0.2616 0.5087 0.0550 1.0000 Uiso R . . . . . . H20 H 0.9064 -0.3339 0.4897 0.0550 1.0000 Uiso R . . . . . . H21 H 0.7751 -0.2567 0.4447 0.0350 1.0000 Uiso R . . . . . . C22 C 0.7537(2) -0.1790(2) 0.33571(11) 0.0327 1.0000 Uani . . . . . . . C23 C 0.8448(3) -0.1625(3) 0.32134(13) 0.0463 1.0000 Uani . . . . . . . C24 C 0.8877(3) -0.2293(4) 0.29392(15) 0.0646 1.0000 Uani . . . . . . . C25 C 0.8433(4) -0.3124(4) 0.28201(16) 0.0748 1.0000 Uani . . . . . . . C26 C 0.7541(4) -0.3310(3) 0.29649(16) 0.0681 1.0000 Uani . . . . . . . C27 C 0.7088(3) -0.2640(3) 0.32309(14) 0.0480 1.0000 Uani . . . . . . . H28 H 0.6469 -0.2757 0.3323 0.0600 1.0000 Uiso R . . . . . . H29 H 0.7240 -0.3876 0.2894 0.0600 1.0000 Uiso R . . . . . . H30 H 0.8732 -0.3560 0.2642 0.0600 1.0000 Uiso R . . . . . . H31 H 0.9467 -0.2161 0.2840 0.0600 1.0000 Uiso R . . . . . . H32 H 0.8761 -0.1062 0.3290 0.0600 1.0000 Uiso R . . . . . . C33 C 0.5603(2) -0.0728(2) 0.29806(10) 0.0254 1.0000 Uani . . . . . . . C34 C 0.6000(2) -0.0737(2) 0.25260(11) 0.0303 1.0000 Uani . . . . . . . C35 C 0.5408(2) -0.0723(2) 0.20565(11) 0.0317 1.0000 Uani . . . . . . . H36 H 0.5687 -0.0714 0.1760 0.0350 1.0000 Uiso R . . . . . . H37 H 0.6672 -0.0740 0.2535 0.0350 1.0000 Uiso R . . . . . . C38 C 0.5983(3) 0.1421(2) 0.37317(13) 0.0472 1.0000 Uani . . . . . . . H39 H 0.6591 0.1568 0.3631 0.0500 1.0000 Uiso R . . . . . . H40 H 0.5502 0.1482 0.3444 0.0500 1.0000 Uiso R . . . . . . H41 H 0.5841 0.1852 0.3975 0.0500 1.0000 Uiso R . . . . . . C42 C 0.4850(2) -0.0007(3) 0.42737(12) 0.0418 1.0000 Uani . . . . . . . H43 H 0.4887 0.0328 0.4586 0.0500 1.0000 Uiso R . . . . . . H44 H 0.4303 0.0196 0.4048 0.0500 1.0000 Uiso R . . . . . . H45 H 0.4793 -0.0650 0.4335 0.0500 1.0000 Uiso R . . . . . . C46 C 0.7182(2) 0.1094(2) 0.50926(11) 0.0286 1.0000 Uani . . . . . . . C47 C 0.7394(2) 0.1415(2) 0.55945(11) 0.0310 1.0000 Uani . . . . . . . H48 H 0.7259 0.2035 0.5672 0.0350 1.0000 Uiso R . . . . . . H49 H 0.6889 0.1496 0.4837 0.0350 1.0000 Uiso R . . . . . . H50 H 0.7965 -0.1015 0.5280 0.0350 1.0000 Uiso R . . . . . . H51 H 0.8295 -0.0486 0.6106 0.0350 1.0000 Uiso R . . . . . . C52 C 1.1016(13) -0.1846(6) 0.6799(4) 0.080(3) 0.84(5) Uiso D . P . . . . C53 C 1.063(5) -0.192(3) 0.6862(15) 0.065(16) 0.16(5) Uiso D . P . . . . Cl54 Cl 1.0348(3) -0.2199(4) 0.61933(11) 0.0787(13) 0.54(1) Uiso D . P . . . . Cl55 Cl 1.0633(5) -0.1813(6) 0.61815(18) 0.086(2) 0.340(11) Uiso D . P . . . . Cl56 Cl 1.1421(10) -0.1277(11) 0.6296(6) 0.104(6) 0.129(6) Uiso D . P . . . . Cl57 Cl 1.1396(11) -0.0705(7) 0.6835(4) 0.065(4) 0.170(13) Uiso D . P . . . . Cl58 Cl 1.1680(8) -0.0907(7) 0.6680(5) 0.082(4) 0.199(10) Uiso D . P . . . . Cl59 Cl 1.087(2) -0.0694(11) 0.6841(6) 0.097(7) 0.118(9) Uiso D . P . . . . Cl60 Cl 1.0308(3) -0.0920(2) 0.71049(14) 0.1004(9) 0.5000 Uiso D . P . . . . 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 Br1 0.0604(2) 0.0522(2) 0.02594(14) -0.00761(17) 0.00276(13) -0.0078(2) C2 0.0267(16) 0.0397(18) 0.0248(13) -0.0024(12) 0.0022(11) -0.0060(14) C3 0.0403(18) 0.0347(18) 0.0259(14) 0.0054(12) 0.0002(12) -0.0006(14) C4 0.0364(18) 0.0259(16) 0.0283(14) 0.0007(11) 0.0038(12) 0.0031(13) C5 0.0177(13) 0.0297(15) 0.0258(13) -0.0013(12) 0.0003(10) -0.0031(12) C6 0.0242(14) 0.0260(15) 0.0238(13) 0.0013(11) -0.0028(10) -0.0004(12) Si7 0.0237(4) 0.0294(4) 0.0222(4) 0.0000(3) -0.0024(3) 0.0035(3) C8 0.0236(14) 0.0298(16) 0.0215(12) -0.0010(11) -0.0022(10) -0.0003(12) C9 0.0261(14) 0.0296(16) 0.0217(12) -0.0011(11) 0.0005(10) -0.0009(12) C10 0.0232(14) 0.0257(15) 0.0219(12) 0.0028(11) -0.0010(10) -0.0015(12) C11 0.0218(13) 0.0337(16) 0.0196(11) -0.0024(11) 0.0002(10) 0.0047(12) C12 0.0374(18) 0.0333(18) 0.0345(16) -0.0016(13) -0.0026(13) 0.0059(15) C13 0.058(2) 0.040(2) 0.0430(19) 0.0007(16) -0.0034(17) 0.0229(19) C14 0.042(2) 0.068(3) 0.044(2) -0.0061(19) -0.0062(16) 0.034(2) C15 0.0195(16) 0.078(3) 0.047(2) -0.017(2) -0.0019(14) 0.0035(17) C16 0.0282(17) 0.0443(19) 0.0345(16) -0.0028(14) 0.0029(13) 0.0002(14) C22 0.0373(18) 0.0371(18) 0.0216(13) -0.0010(12) -0.0028(12) 0.0128(15) C23 0.044(2) 0.063(2) 0.0329(17) 0.0009(17) 0.0072(15) 0.0153(19) C24 0.054(3) 0.102(4) 0.039(2) 0.005(2) 0.0130(18) 0.037(3) C25 0.105(4) 0.079(4) 0.040(2) -0.012(2) 0.006(2) 0.051(3) C26 0.107(4) 0.044(2) 0.049(2) -0.0127(19) -0.006(2) 0.021(3) C27 0.062(3) 0.037(2) 0.044(2) -0.0056(15) 0.0008(17) 0.0086(18) C33 0.0254(15) 0.0253(16) 0.0244(13) -0.0009(11) -0.0004(11) 0.0022(12) C34 0.0230(15) 0.0417(19) 0.0254(14) 0.0012(13) 0.0002(11) -0.0003(13) C35 0.0290(16) 0.046(2) 0.0195(13) 0.0036(13) 0.0010(11) -0.0006(14) C38 0.064(3) 0.038(2) 0.0358(17) 0.0061(15) -0.0053(16) 0.0067(18) C42 0.0320(17) 0.060(2) 0.0330(16) -0.0079(16) 0.0041(13) 0.0025(16) C46 0.0228(14) 0.0347(18) 0.0267(13) 0.0007(12) -0.0023(11) 0.0044(13) C47 0.0254(16) 0.0326(18) 0.0345(15) -0.0043(12) 0.0032(12) 0.0014(12) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.6414(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Br1 . C2 . 1.897(3) yes C2 . C3 . 1.380(5) yes C2 . C47 . 1.370(4) yes C3 . C4 . 1.386(4) yes C3 . H51 . 0.914 no C4 . C5 . 1.399(4) yes C4 . H50 . 0.927 no C5 . C6 . 1.481(4) yes C5 . C46 . 1.394(4) yes C6 . Si7 . 1.878(3) yes C6 . C10 . 1.352(4) yes Si7 . C8 . 1.868(3) yes Si7 . C38 . 1.850(3) yes Si7 . C42 . 1.854(3) yes C8 . C9 . 1.356(4) yes C8 . C33 . 1.478(4) yes C9 . C10 . 1.497(4) yes C9 . C22 . 1.491(4) yes C10 . C11 . 1.487(4) yes C11 . C12 . 1.387(4) yes C11 . C16 . 1.389(4) yes C12 . C13 . 1.378(5) yes C12 . H21 . 0.939 no C13 . C14 . 1.361(6) yes C13 . H20 . 0.921 no C14 . C15 . 1.369(6) yes C14 . H19 . 0.919 no C15 . C16 . 1.390(5) yes C15 . H18 . 0.904 no C16 . H17 . 0.926 no C22 . C23 . 1.390(5) yes C22 . C27 . 1.386(5) yes C23 . C24 . 1.384(6) yes C23 . H32 . 0.924 no C24 . C25 . 1.356(7) yes C24 . H31 . 0.913 no C25 . C26 . 1.372(7) yes C25 . H30 . 0.915 no C26 . C27 . 1.391(6) yes C26 . H29 . 0.919 no C27 . H28 . 0.939 no C33 . C35 5_655 1.392(4) yes C33 . C34 . 1.389(4) yes C34 . C35 . 1.384(4) yes C34 . H37 . 0.929 no C35 . H36 . 0.922 no C38 . H39 . 0.944 no C38 . H40 . 0.939 no C38 . H41 . 0.932 no C42 . H43 . 0.949 no C42 . H44 . 0.941 no C42 . H45 . 0.941 no C46 . C47 . 1.392(4) yes C46 . H49 . 0.933 no C47 . H48 . 0.936 no C52 . Cl54 . 1.800(9) yes C52 . Cl55 . 1.639(9) yes C52 . Cl56 . 1.72(2) yes C52 . Cl57 . 1.716(14) yes C52 . Cl58 . 1.684(17) yes C52 . Cl59 . 1.667(18) yes C52 . Cl60 . 1.899(13) yes C53 . Cl54 . 1.80(4) yes C53 . Cl55 . 1.80(5) yes C53 . Cl56 . 2.18(7) yes C53 . Cl57 . 2.04(6) yes C53 . Cl58 . 2.15(7) yes C53 . Cl59 . 1.78(5) yes C53 . Cl60 . 1.65(4) yes Cl54 . Cl56 . 1.979(16) yes Cl55 . Cl56 . 1.334(17) yes Cl55 . Cl57 . 2.466(14) yes Cl55 . Cl58 . 2.230(13) yes Cl55 . Cl59 . 2.353(17) yes Cl56 . Cl57 . 1.65(2) yes Cl56 . Cl58 . 1.155(18) yes Cl56 . Cl59 . 1.91(2) yes Cl57 . Cl60 . 1.786(16) yes Cl58 . Cl59 . 1.29(3) yes Cl58 . Cl60 . 2.343(15) yes Cl59 . Cl60 . 1.17(2) yes Cl60 . Cl60 5_756 2.363(7) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag Br1 . C2 . C3 . 119.0(2) yes Br1 . C2 . C47 . 120.5(2) yes C3 . C2 . C47 . 120.5(3) yes C2 . C3 . C4 . 119.8(3) yes C2 . C3 . H51 . 120.1 no C4 . C3 . H51 . 120.1 no C3 . C4 . C5 . 121.5(3) yes C3 . C4 . H50 . 118.7 no C5 . C4 . H50 . 119.8 no C4 . C5 . C6 . 123.2(3) yes C4 . C5 . C46 . 116.9(3) yes C6 . C5 . C46 . 119.8(3) yes C5 . C6 . Si7 . 125.6(2) yes C5 . C6 . C10 . 127.0(3) yes Si7 . C6 . C10 . 107.0(2) yes C6 . Si7 . C8 . 92.15(13) yes C6 . Si7 . C38 . 115.39(16) yes C8 . Si7 . C38 . 110.25(15) yes C6 . Si7 . C42 . 112.36(14) yes C8 . Si7 . C42 . 114.37(15) yes C38 . Si7 . C42 . 111.15(18) yes Si7 . C8 . C9 . 108.1(2) yes Si7 . C8 . C33 . 124.0(2) yes C9 . C8 . C33 . 127.5(3) yes C8 . C9 . C10 . 115.4(3) yes C8 . C9 . C22 . 125.3(3) yes C10 . C9 . C22 . 119.3(2) yes C9 . C10 . C6 . 117.2(2) yes C9 . C10 . C11 . 118.5(2) yes C6 . C10 . C11 . 124.2(2) yes C10 . C11 . C12 . 119.1(3) yes C10 . C11 . C16 . 121.8(3) yes C12 . C11 . C16 . 119.0(3) yes C11 . C12 . C13 . 120.5(3) yes C11 . C12 . H21 . 119.4 no C13 . C12 . H21 . 120.1 no C12 . C13 . C14 . 120.1(4) yes C12 . C13 . H20 . 119.9 no C14 . C13 . H20 . 120.0 no C13 . C14 . C15 . 120.4(3) yes C13 . C14 . H19 . 119.1 no C15 . C14 . H19 . 120.5 no C14 . C15 . C16 . 120.3(3) yes C14 . C15 . H18 . 120.9 no C16 . C15 . H18 . 118.7 no C15 . C16 . C11 . 119.5(3) yes C15 . C16 . H17 . 120.7 no C11 . C16 . H17 . 119.7 no C9 . C22 . C23 . 120.8(3) yes C9 . C22 . C27 . 120.6(3) yes C23 . C22 . C27 . 118.6(3) yes C22 . C23 . C24 . 120.0(4) yes C22 . C23 . H32 . 120.4 no C24 . C23 . H32 . 119.5 no C23 . C24 . C25 . 120.8(5) yes C23 . C24 . H31 . 118.4 no C25 . C24 . H31 . 120.8 no C24 . C25 . C26 . 120.2(4) yes C24 . C25 . H30 . 119.6 no C26 . C25 . H30 . 120.2 no C25 . C26 . C27 . 119.8(5) yes C25 . C26 . H29 . 121.1 no C27 . C26 . H29 . 119.0 no C26 . C27 . C22 . 120.4(4) yes C26 . C27 . H28 . 120.2 no C22 . C27 . H28 . 119.3 no C8 . C33 . C35 5_655 119.8(3) yes C8 . C33 . C34 . 122.6(3) yes C35 5_655 C33 . C34 . 117.3(3) yes C33 . C34 . C35 . 120.9(3) yes C33 . C34 . H37 . 119.8 no C35 . C34 . H37 . 119.2 no C33 5_655 C35 . C34 . 121.7(3) yes C33 5_655 C35 . H36 . 118.8 no C34 . C35 . H36 . 119.5 no Si7 . C38 . H39 . 111.3 no Si7 . C38 . H40 . 109.9 no H39 . C38 . H40 . 108.2 no Si7 . C38 . H41 . 110.5 no H39 . C38 . H41 . 109.4 no H40 . C38 . H41 . 107.4 no Si7 . C42 . H43 . 108.7 no Si7 . C42 . H44 . 109.7 no H43 . C42 . H44 . 109.4 no Si7 . C42 . H45 . 109.8 no H43 . C42 . H45 . 109.9 no H44 . C42 . H45 . 109.3 no C5 . C46 . C47 . 121.9(3) yes C5 . C46 . H49 . 118.6 no C47 . C46 . H49 . 119.6 no C46 . C47 . C2 . 119.5(3) yes C46 . C47 . H48 . 119.9 no C2 . C47 . H48 . 120.7 no Cl54 . C52 . Cl55 . 22.3(3) yes Cl54 . C52 . Cl56 . 68.4(6) yes Cl55 . C52 . Cl56 . 46.8(7) yes Cl54 . C52 . Cl57 . 115.6(6) yes Cl55 . C52 . Cl57 . 94.6(7) yes Cl56 . C52 . Cl57 . 57.3(8) yes Cl54 . C52 . Cl58 . 106.6(7) yes Cl55 . C52 . Cl58 . 84.3(8) yes Cl56 . C52 . Cl58 . 39.7(7) yes Cl57 . C52 . Cl58 . 22.8(5) yes Cl54 . C52 . Cl59 . 106.7(8) yes Cl55 . C52 . Cl59 . 90.8(7) yes Cl56 . C52 . Cl59 . 68.8(9) yes Cl57 . C52 . Cl59 . 24.8(8) yes Cl58 . C52 . Cl59 . 45.3(11) yes Cl54 . C52 . Cl60 . 110.0(7) yes Cl55 . C52 . Cl60 . 106.7(6) yes Cl56 . C52 . Cl60 . 104.1(6) yes Cl57 . C52 . Cl60 . 59.0(6) yes Cl58 . C52 . Cl60 . 81.4(6) yes Cl59 . C52 . Cl60 . 37.4(9) yes Cl54 . C53 . Cl55 . 21.9(5) yes Cl54 . C53 . Cl56 . 58.9(18) yes Cl55 . C53 . Cl56 . 37.7(14) yes Cl54 . C53 . Cl57 . 102(3) yes Cl55 . C53 . Cl57 . 80(2) yes Cl56 . C53 . Cl57 . 45.8(16) yes Cl54 . C53 . Cl58 . 90(3) yes Cl55 . C53 . Cl58 . 68(2) yes Cl56 . C53 . Cl58 . 31.0(11) yes Cl57 . C53 . Cl58 . 18.2(7) yes Cl54 . C53 . Cl59 . 102(2) yes Cl55 . C53 . Cl59 . 82(2) yes Cl56 . C53 . Cl59 . 56.8(20) yes Cl57 . C53 . Cl59 . 20.6(11) yes Cl58 . C53 . Cl59 . 36.8(16) yes Cl54 . C53 . Cl60 . 123(2) yes Cl55 . C53 . Cl60 . 110.8(20) yes Cl56 . C53 . Cl60 . 95(2) yes Cl57 . C53 . Cl60 . 56.7(15) yes Cl58 . C53 . Cl60 . 74.8(20) yes Cl59 . C53 . Cl60 . 39.4(12) yes C52 . Cl54 . C53 . 19(2) yes C52 . Cl54 . Cl56 . 53.8(7) yes C53 . Cl54 . Cl56 . 70(2) yes C53 . Cl55 . C52 . 19.0(18) yes C53 . Cl55 . Cl56 . 87(2) yes C52 . Cl55 . Cl56 . 69.8(9) yes C53 . Cl55 . Cl57 . 54.4(18) yes C52 . Cl55 . Cl57 . 43.9(5) yes Cl56 . Cl55 . Cl57 . 38.4(8) yes C53 . Cl55 . Cl58 . 63(2) yes C52 . Cl55 . Cl58 . 48.7(6) yes Cl56 . Cl55 . Cl58 . 24.4(7) yes Cl57 . Cl55 . Cl58 . 15.4(4) yes C53 . Cl55 . Cl59 . 48.6(14) yes C52 . Cl55 . Cl59 . 45.1(5) yes Cl56 . Cl55 . Cl59 . 54.4(9) yes Cl57 . Cl55 . Cl59 . 17.2(6) yes Cl58 . Cl55 . Cl59 . 32.5(8) yes C52 . Cl56 . Cl54 . 57.7(6) yes C52 . Cl56 . C53 . 11.1(12) yes Cl54 . Cl56 . C53 . 51.0(11) yes C52 . Cl56 . Cl55 . 63.5(7) yes Cl54 . Cl56 . Cl55 . 8.0(3) yes C53 . Cl56 . Cl55 . 55.7(13) yes C52 . Cl56 . Cl57 . 61.3(6) yes Cl54 . Cl56 . Cl57 . 110.0(9) yes C53 . Cl56 . Cl57 . 62.7(11) yes Cl55 . Cl56 . Cl57 . 111.3(10) yes C52 . Cl56 . Cl58 . 68.6(9) yes Cl54 . Cl56 . Cl58 . 124.0(12) yes C53 . Cl56 . Cl58 . 73.4(14) yes Cl55 . Cl56 . Cl58 . 127.1(14) yes Cl57 . Cl56 . Cl58 . 19.2(8) yes C52 . Cl56 . Cl59 . 54.3(7) yes Cl54 . Cl56 . Cl59 . 91.2(9) yes C53 . Cl56 . Cl59 . 51.2(11) yes Cl55 . Cl56 . Cl59 . 91.1(11) yes Cl57 . Cl56 . Cl59 . 22.0(6) yes Cl58 . Cl56 . Cl59 . 41.1(12) yes C52 . Cl57 . C53 . 15.2(14) yes C52 . Cl57 . Cl55 . 41.5(4) yes C53 . Cl57 . Cl55 . 45.9(12) yes C52 . Cl57 . Cl56 . 61.4(8) yes C53 . Cl57 . Cl56 . 71.5(16) yes Cl55 . Cl57 . Cl56 . 30.3(6) yes C52 . Cl57 . Cl60 . 65.7(7) yes C53 . Cl57 . Cl60 . 50.6(18) yes Cl55 . Cl57 . Cl60 . 82.3(5) yes Cl56 . Cl57 . Cl60 . 112.5(8) yes Cl55 . Cl58 . C52 . 47.0(4) yes Cl55 . Cl58 . C53 . 48.5(10) yes C52 . Cl58 . C53 . 10.9(12) yes Cl55 . Cl58 . Cl56 . 28.5(8) yes C52 . Cl58 . Cl56 . 71.7(9) yes C53 . Cl58 . Cl56 . 75.7(13) yes Cl55 . Cl58 . Cl59 . 79.0(9) yes C52 . Cl58 . Cl59 . 66.7(10) yes C53 . Cl58 . Cl59 . 55.9(16) yes Cl56 . Cl58 . Cl59 . 102.8(13) yes Cl55 . Cl58 . Cl60 . 76.8(4) yes C52 . Cl58 . Cl60 . 53.3(6) yes C53 . Cl58 . Cl60 . 42.9(14) yes Cl56 . Cl58 . Cl60 . 104.1(10) yes Cl59 . Cl58 . Cl60 . 16.5(7) yes C53 . Cl59 . C52 . 19.3(19) yes C53 . Cl59 . Cl55 . 49.3(15) yes C52 . Cl59 . Cl55 . 44.1(5) yes C53 . Cl59 . Cl56 . 72(2) yes C52 . Cl59 . Cl56 . 56.9(9) yes Cl55 . Cl59 . Cl56 . 34.5(5) yes C53 . Cl59 . Cl58 . 87(3) yes C52 . Cl59 . Cl58 . 68.1(11) yes Cl55 . Cl59 . Cl58 . 68.5(9) yes Cl56 . Cl59 . Cl58 . 36.1(7) yes C53 . Cl59 . Cl60 . 64(2) yes C52 . Cl59 . Cl60 . 82.2(12) yes Cl55 . Cl59 . Cl60 . 102.5(12) yes Cl56 . Cl59 . Cl60 . 134.6(13) yes Cl58 . Cl59 . Cl60 . 145.2(16) yes C52 . Cl60 . Cl58 . 45.3(6) yes C52 . Cl60 . C53 . 17(2) yes Cl58 . Cl60 . C53 . 62(3) yes C52 . Cl60 . Cl60 5_756 130.5(4) yes Cl58 . Cl60 . Cl60 5_756 147.4(3) yes C53 . Cl60 . Cl60 5_756 120(2) yes C52 . Cl60 . Cl57 . 55.4(6) yes Cl58 . Cl60 . Cl57 . 10.5(4) yes C53 . Cl60 . Cl57 . 73(3) yes Cl60 5_756 Cl60 . Cl57 . 141.7(4) yes C52 . Cl60 . Cl59 . 60.4(10) yes Cl58 . Cl60 . Cl59 . 18.3(10) yes C53 . Cl60 . Cl59 . 76(3) yes Cl60 5_756 Cl60 . Cl59 . 152.2(10) yes Cl57 . Cl60 . Cl59 . 15.2(11) yes