# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _publ_contact_author_name 'Bao, Zhenan' _publ_contact_author_email zbao@stanford.edu _publ_section_title ; Synthesis of Regioregular Pentacene-containing Conjugated Polymers ; _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ? _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? # PROCESSING SUMMARY (IUCr Office Use Only): _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ? _journal_volume ? _journal_year ? _publ_contact_author_address ; Bell Laboratories room 1D-436 Alcatel-Lucent 600 Mountain Avenue Murray Hill, NJ 07974 ; _publ_contact_author_fax '+1 908 582 4868' _publ_contact_author_phone '+1 908 582 5253' # 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_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Acta Crystallographica E. The figures will be sent by e-mail. ; _publ_requested_category EO # choose from: FI FM FO CI CM CO AD _publ_requested_coeditor_name 'Prof William Clegg' loop_ _publ_author_name T.Okamoto 'Ying Jiang.' H.Becerril S.Hong M.Senatore 'Ming Tang.' ; M.Toney ; T.Siegrist 'Zhenan Bao.' # Attachment '- 2,10-TIPS-Br-pentacene_150K.cif' data_2,10-TIPS-Br-pentacene_150K _database_code_depnum_ccdc_archive 'CCDC 734417' #TrackingRef '- 2,10-TIPS-Br-pentacene_150K.cif' _audit_creation_date 07-08-27 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title CRYSTALS_cif _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 8.5917(5) _cell_length_b 14.2392(14) _cell_length_c 17.7698(16) _cell_angle_alpha 95.665(10) _cell_angle_beta 98.824(10) _cell_angle_gamma 103.551(10) _cell_volume 2067.8(3) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z 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' 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' 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' _cell_formula_units_Z 8 # Given Formula = C11 H11.75 Br0.50 Si0.50 # Dc = 1.27 Fooo = 828.00 Mu = 20.46 M = 791.84 # Found Formula = C11 H13 Br0.50 Si0.50 # Dc = 1.28 FOOO = 828.00 Mu = 20.46 M = 796.88 _chemical_formula_sum 'C11 H13 Br0.50 Si0.50' _chemical_formula_moiety 'C11 H13 Br0.50 Si0.50' _chemical_compound_source ? _chemical_formula_weight 199.22 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 150 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_min 0.04 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_max 0.15 _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 828 _exptl_absorpt_coefficient_mu 2.046 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details '(North et al., 1968)' _exptl_absorpt_correction_T_min 0.91 _exptl_absorpt_correction_T_max 1.00 _diffrn_measurement_device_type 'Oxford Diffraction XCALIBUR' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Xcalibur, (Oxford Diffraction, 2002)' _computing_cell_refinement 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_structure_solution 'USER DEFINED STRUCTURE SOLUTION' _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 ? _diffrn_standards_number ? _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 31889 _reflns_number_total 13406 _diffrn_reflns_av_R_equivalents 0.042 # Number of reflections with Friedels Law is 13406 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 10458 _diffrn_reflns_theta_min 2.480 _diffrn_reflns_theta_max 33.075 _diffrn_measured_fraction_theta_max 0.855 _diffrn_reflns_theta_full 25.137 _diffrn_measured_fraction_theta_full 0.975 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _reflns_limit_h_min -12 _reflns_limit_h_max 12 _reflns_limit_k_min -21 _reflns_limit_k_max 21 _reflns_limit_l_min 0 _reflns_limit_l_max 26 _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 -1.00 _refine_diff_density_max 1.37 _refine_ls_number_reflns 9954 _refine_ls_number_restraints 0 _refine_ls_number_parameters 433 #_refine_ls_R_factor_ref 0.0720 _refine_ls_wR_factor_ref 0.1088 _refine_ls_goodness_of_fit_ref 0.7655 #_reflns_number_all 9954 _refine_ls_R_factor_all 0.0720 _refine_ls_wR_factor_all 0.1088 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 5761 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_gt 0.1037 _refine_ls_shift/su_max 0.000597 # 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 Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment noref # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.07P)^2^ + 0.00P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ; _publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fih. ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; _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 absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. 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. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. North, A.C.T., Phillips, D.C. & Mathews, F.S., (1968). Acta Cryst, A24, 351-359. Oxford Diffraction, (2002). CrysAlis RED. Oxford Diffraction, (2002). Xcalibur User Manual. 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 _atom_site_attached_hydrogens C1 C -0.1478(3) 0.22239(19) 0.42545(15) 0.0243 1.0000 Uani . . . . . . C2 C -0.1007(3) 0.22031(19) 0.50661(15) 0.0254 1.0000 Uani . . . . . . C3 C 0.0656(3) 0.25398(19) 0.54135(15) 0.0260 1.0000 Uani . . . . . . C4 C 0.1855(3) 0.29350(19) 0.49855(15) 0.0246 1.0000 Uani . . . . . . C5 C 0.1373(3) 0.29690(19) 0.41755(15) 0.0249 1.0000 Uani . . . . . . C6 C -0.0286(3) 0.2595(2) 0.38200(15) 0.0261 1.0000 Uani . . . . . . C7 C -0.0756(3) 0.25628(19) 0.30103(16) 0.0259 1.0000 Uani . . . . . . C8 C -0.1195(3) 0.2518(2) 0.23288(16) 0.0288 1.0000 Uani . . . . . . Si9 Si -0.19485(10) 0.24354(6) 0.12975(4) 0.0299 1.0000 Uani . . . . . . C10 C -0.4222(4) 0.2213(2) 0.11577(18) 0.0399 1.0000 Uani . . . . . . C11 C -0.5039(4) 0.1257(3) 0.1426(3) 0.0627 1.0000 Uani . . . . . . C12 C -0.4728(5) 0.3060(3) 0.1570(3) 0.0691 1.0000 Uani . . . . . . C13 C -0.1427(4) 0.1334(3) 0.0823(2) 0.0538 1.0000 Uani . . . . . . C14 C 0.0303(6) 0.1344(4) 0.0971(3) 0.1033 1.0000 Uani . . . . . . C15 C -0.2203(5) 0.1029(3) -0.0020(2) 0.0688 1.0000 Uani . . . . . . C16 C -0.1038(5) 0.3652(3) 0.1008(2) 0.0522 1.0000 Uani . . . . . . C17 C 0.0772(6) 0.4005(4) 0.1229(3) 0.0904 1.0000 Uani . . . . . . C18 C -0.1653(6) 0.3697(3) 0.0154(2) 0.0738 1.0000 Uani . . . . . . C19 C 0.2582(3) 0.3369(2) 0.37602(15) 0.0276 1.0000 Uani . . . . . . C20 C 0.4206(3) 0.37235(19) 0.41001(15) 0.0262 1.0000 Uani . . . . . . C21 C 0.4678(3) 0.3670(2) 0.49086(15) 0.0269 1.0000 Uani . . . . . . C22 C 0.3510(3) 0.3292(2) 0.53221(15) 0.0268 1.0000 Uani . . . . . . C23 C 0.6380(4) 0.4019(2) 0.52395(16) 0.0322 1.0000 Uani . . . . . . C24 C 0.7507(3) 0.4382(2) 0.48302(17) 0.0321 1.0000 Uani . . . . . . C25 C 0.7009(3) 0.4439(2) 0.40377(17) 0.0293 1.0000 Uani . . . . . . C26 C 0.5425(4) 0.4126(2) 0.36825(16) 0.0298 1.0000 Uani . . . . . . Br27 Br 0.86375(4) 0.49622(2) 0.347492(19) 0.0380 1.0000 Uani . . . . . . C28 C 0.1126(3) 0.2497(2) 0.62118(15) 0.0259 1.0000 Uani . . . . . . C29 C 0.1480(4) 0.2461(2) 0.68872(16) 0.0312 1.0000 Uani . . . . . . Si30 Si 0.19095(12) 0.25181(7) 0.79376(5) 0.0384 1.0000 Uani . . . . . . C31 C 0.3158(5) 0.3796(3) 0.8325(2) 0.0515 1.0000 Uani . . . . . . C32 C 0.3396(7) 0.4039(3) 0.9207(2) 0.0876 1.0000 Uani . . . . . . C33 C 0.4754(5) 0.4049(3) 0.8043(3) 0.0824 1.0000 Uani . . . . . . C34 C -0.0102(5) 0.2297(3) 0.82602(19) 0.0579 1.0000 Uani . . . . . . C35 C -0.0993(6) 0.3088(4) 0.8057(3) 0.0892 1.0000 Uani . . . . . . C36 C -0.1227(6) 0.1292(4) 0.7943(2) 0.0855 1.0000 Uani . . . . . . C37 C 0.2998(7) 0.1562(3) 0.8187(2) 0.0801 1.0000 Uani . . . . . . C39 C 0.3208(7) 0.1441(3) 0.9018(2) 0.0888 1.0000 Uani . . . . . . C40 C -0.2223(4) 0.1835(2) 0.54825(15) 0.0279 1.0000 Uani . . . . . . C41 C -0.3852(4) 0.1500(2) 0.51480(16) 0.0287 1.0000 Uani . . . . . . C42 C -0.4316(3) 0.1517(2) 0.43336(16) 0.0281 1.0000 Uani . . . . . . C43 C -0.3136(3) 0.1875(2) 0.39145(15) 0.0279 1.0000 Uani . . . . . . C44 C -0.6010(3) 0.1147(2) 0.39852(17) 0.0309 1.0000 Uani . . . . . . C45 C -0.7104(3) 0.0796(2) 0.44134(18) 0.0317 1.0000 Uani . . . . . . C46 C -0.6672(4) 0.0773(2) 0.52206(18) 0.0358 1.0000 Uani . . . . . . C47 C -0.5101(4) 0.1123(2) 0.55612(17) 0.0344 1.0000 Uani . . . . . . Br48 Br -0.93234(4) 0.02885(2) 0.39439(2) 0.0425 1.0000 Uani . . . . . . C9 C 0.3279(10) 0.0928(6) 0.7632(3) 0.1612 1.0000 Uani . . . . . . H101 H -0.4655 0.2164 0.0619 0.0572 1.0000 Uiso . . . . . . H111 H -0.6171 0.1142 0.1366 0.1050 1.0000 Uiso . . . . . . H112 H -0.4580 0.1200 0.1947 0.1051 1.0000 Uiso . . . . . . H113 H -0.4823 0.0726 0.1103 0.1044 1.0000 Uiso . . . . . . H121 H -0.5867 0.2945 0.1476 0.1222 1.0000 Uiso . . . . . . H122 H -0.4338 0.3135 0.2108 0.1227 1.0000 Uiso . . . . . . H123 H -0.4245 0.3640 0.1380 0.1228 1.0000 Uiso . . . . . . H131 H -0.1952 0.0801 0.1096 0.0789 1.0000 Uiso . . . . . . H151 H -0.2023 0.0422 -0.0216 0.1238 1.0000 Uiso . . . . . . H152 H -0.3355 0.0972 -0.0082 0.1237 1.0000 Uiso . . . . . . H153 H -0.1751 0.1532 -0.0309 0.1239 1.0000 Uiso . . . . . . H161 H -0.1447 0.4149 0.1309 0.0774 1.0000 Uiso . . . . . . H171 H 0.1161 0.4657 0.1114 0.1466 1.0000 Uiso . . . . . . H172 H 0.1124 0.4045 0.1785 0.1468 1.0000 Uiso . . . . . . H173 H 0.1289 0.3571 0.0968 0.1470 1.0000 Uiso . . . . . . H181 H -0.1332 0.4360 0.0056 0.1348 1.0000 Uiso . . . . . . H182 H -0.2819 0.3486 0.0031 0.1347 1.0000 Uiso . . . . . . H183 H -0.1160 0.3305 -0.0159 0.1349 1.0000 Uiso . . . . . . H191 H 0.2257 0.3389 0.3240 0.0390 1.0000 Uiso . . . . . . H221 H 0.3811 0.3259 0.5845 0.0385 1.0000 Uiso . . . . . . H231 H 0.6695 0.3992 0.5776 0.0438 1.0000 Uiso . . . . . . H241 H 0.8657 0.4606 0.5074 0.0446 1.0000 Uiso . . . . . . H261 H 0.5154 0.4167 0.3164 0.0427 1.0000 Uiso . . . . . . H311 H 0.2527 0.4218 0.8106 0.0715 1.0000 Uiso . . . . . . H321 H 0.3838 0.4708 0.9368 0.1498 1.0000 Uiso . . . . . . H322 H 0.2376 0.3829 0.9383 0.1497 1.0000 Uiso . . . . . . H323 H 0.4132 0.3704 0.9444 0.1495 1.0000 Uiso . . . . . . H331 H 0.5320 0.4719 0.8230 0.1356 1.0000 Uiso . . . . . . H332 H 0.5446 0.3673 0.8234 0.1359 1.0000 Uiso . . . . . . H333 H 0.4615 0.3993 0.7494 0.1356 1.0000 Uiso . . . . . . H341 H 0.0112 0.2370 0.8817 0.0847 1.0000 Uiso . . . . . . H351 H -0.2000 0.2957 0.8241 0.1615 1.0000 Uiso . . . . . . H352 H -0.0331 0.3703 0.8292 0.1618 1.0000 Uiso . . . . . . H353 H -0.1224 0.3077 0.7508 0.1614 1.0000 Uiso . . . . . . H361 H -0.2221 0.1168 0.8124 0.1409 1.0000 Uiso . . . . . . H362 H -0.0701 0.0768 0.8104 0.1410 1.0000 Uiso . . . . . . H363 H -0.1480 0.1159 0.7392 0.1406 1.0000 Uiso . . . . . . H391 H 0.3927 0.1019 0.9134 0.1468 1.0000 Uiso . . . . . . H392 H 0.3661 0.2036 0.9344 0.1468 1.0000 Uiso . . . . . . H393 H 0.2179 0.1149 0.9136 0.1470 1.0000 Uiso . . . . . . H401 H -0.1927 0.1832 0.6012 0.0411 1.0000 Uiso . . . . . . H431 H -0.3434 0.1875 0.3392 0.0405 1.0000 Uiso . . . . . . H441 H -0.6332 0.1145 0.3449 0.0455 1.0000 Uiso . . . . . . H461 H -0.7574 0.0502 0.5508 0.0532 1.0000 Uiso . . . . . . H471 H -0.4824 0.1122 0.6099 0.0513 1.0000 Uiso . . . . . . H141 H 0.0766 0.1536 0.1546 0.1192 1.0000 Uiso . . . . . . H142 H 0.0922 0.1837 0.0692 0.1192 1.0000 Uiso . . . . . . H143 H 0.0467 0.0688 0.0812 0.1192 1.0000 Uiso . . . . . . H91 H 0.3122 0.1199 0.7120 0.2163 1.0000 Uiso . . . . . . H92 H 0.4417 0.0855 0.7737 0.2163 1.0000 Uiso . . . . . . H93 H 0.2483 0.0298 0.7590 0.2163 1.0000 Uiso . . . . . . H371 H 0.4176 0.2029 0.8241 0.1091 1.0000 Uiso . . . . . . 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 C1 0.0299(14) 0.0216(13) 0.0225(14) 0.0003(11) 0.0032(11) 0.0112(11) C2 0.0388(16) 0.0210(13) 0.0192(14) 0.0015(11) 0.0041(12) 0.0146(12) C3 0.0375(16) 0.0236(14) 0.0177(14) 0.0006(11) 0.0024(11) 0.0122(12) C4 0.0368(15) 0.0221(14) 0.0159(13) 0.0000(11) 0.0026(11) 0.0119(12) C5 0.0357(15) 0.0225(14) 0.0161(13) 0.0000(11) -0.0005(11) 0.0112(12) C6 0.0371(15) 0.0243(14) 0.0184(14) 0.0028(11) 0.0044(12) 0.0112(12) C7 0.0286(14) 0.0247(14) 0.0230(15) 0.0019(11) 0.0036(12) 0.0052(11) C8 0.0322(15) 0.0276(15) 0.0247(15) 0.0043(12) 0.0044(12) 0.0043(12) Si9 0.0364(4) 0.0369(5) 0.0154(4) 0.0019(3) -0.0004(3) 0.0116(4) C10 0.0379(17) 0.046(2) 0.0316(17) -0.0053(15) -0.0053(14) 0.0154(15) C11 0.040(2) 0.060(3) 0.074(3) -0.006(2) 0.0029(19) -0.0033(18) C12 0.051(2) 0.066(3) 0.092(3) -0.010(2) 0.009(2) 0.028(2) C13 0.054(2) 0.067(3) 0.039(2) -0.0168(18) -0.0023(17) 0.0290(19) C14 0.065(3) 0.124(5) 0.112(4) -0.053(4) -0.009(3) 0.050(3) C15 0.089(3) 0.081(3) 0.033(2) -0.024(2) 0.002(2) 0.036(3) C16 0.060(2) 0.058(2) 0.039(2) 0.0239(17) 0.0022(17) 0.0113(19) C17 0.076(3) 0.085(3) 0.098(4) 0.050(3) 0.005(3) -0.013(3) C18 0.094(3) 0.088(3) 0.044(2) 0.039(2) 0.008(2) 0.024(3) C19 0.0389(16) 0.0291(15) 0.0156(14) 0.0025(11) 0.0026(12) 0.0118(13) C20 0.0335(15) 0.0228(14) 0.0217(14) 0.0002(11) 0.0014(12) 0.0094(12) C21 0.0361(15) 0.0237(14) 0.0208(14) -0.0003(11) 0.0006(12) 0.0115(12) C22 0.0368(16) 0.0251(14) 0.0172(14) -0.0010(11) -0.0018(12) 0.0115(12) C23 0.0412(17) 0.0285(15) 0.0242(15) -0.0003(12) -0.0024(13) 0.0108(13) C24 0.0308(15) 0.0309(16) 0.0314(16) 0.0021(13) -0.0019(13) 0.0073(13) C25 0.0327(15) 0.0241(14) 0.0320(16) 0.0033(12) 0.0076(13) 0.0082(12) C26 0.0393(16) 0.0261(15) 0.0241(15) 0.0023(12) 0.0043(12) 0.0102(13) Br27 0.03936(18) 0.03339(18) 0.03976(19) 0.00539(14) 0.00924(14) 0.00459(14) C28 0.0316(15) 0.0267(14) 0.0198(14) -0.0001(11) 0.0028(11) 0.0110(12) C29 0.0391(16) 0.0311(16) 0.0229(15) 0.0036(12) 0.0030(13) 0.0099(13) Si30 0.0543(5) 0.0463(5) 0.0157(4) 0.0040(4) -0.0014(4) 0.0201(4) C31 0.064(2) 0.050(2) 0.0348(19) -0.0044(16) -0.0152(17) 0.0240(19) C32 0.153(5) 0.062(3) 0.036(2) -0.014(2) -0.027(3) 0.041(3) C33 0.063(3) 0.062(3) 0.103(4) -0.011(3) -0.003(3) 0.000(2) C34 0.063(2) 0.088(3) 0.0201(17) 0.0023(18) 0.0113(16) 0.014(2) C35 0.081(3) 0.139(5) 0.064(3) 0.002(3) 0.021(3) 0.059(3) C36 0.078(3) 0.119(4) 0.044(2) 0.011(3) 0.017(2) -0.009(3) C37 0.146(5) 0.070(3) 0.040(2) 0.013(2) 0.001(3) 0.065(3) C39 0.138(5) 0.067(3) 0.046(3) 0.013(2) -0.037(3) 0.029(3) C40 0.0411(17) 0.0252(14) 0.0200(14) 0.0037(11) 0.0037(12) 0.0146(13) C41 0.0413(17) 0.0257(15) 0.0226(15) 0.0041(12) 0.0082(13) 0.0137(13) C42 0.0331(15) 0.0244(14) 0.0279(15) 0.0010(12) 0.0040(12) 0.0116(12) C43 0.0381(16) 0.0275(15) 0.0197(14) 0.0042(11) 0.0029(12) 0.0130(13) C44 0.0339(16) 0.0294(15) 0.0305(16) 0.0035(13) 0.0040(13) 0.0115(13) C45 0.0288(15) 0.0255(15) 0.0397(18) 0.0000(13) 0.0052(13) 0.0074(12) C46 0.0399(17) 0.0314(16) 0.0398(19) 0.0062(14) 0.0149(15) 0.0113(14) C47 0.0463(19) 0.0318(16) 0.0298(17) 0.0060(13) 0.0120(14) 0.0149(14) Br48 0.03630(18) 0.03775(19) 0.0519(2) 0.00379(15) 0.00857(15) 0.00683(14) C9 0.266(9) 0.223(8) 0.074(4) 0.038(5) 0.023(5) 0.215(8) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.029(2) 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 C1 . C2 . 1.442(4) yes C1 . C6 . 1.412(4) yes C1 . C43 . 1.409(4) yes C2 . C3 . 1.416(4) yes C2 . C40 . 1.403(4) yes C3 . C4 . 1.417(4) yes C3 . C28 . 1.425(4) yes C4 . C5 . 1.444(4) yes C4 . C22 . 1.407(4) yes C5 . C6 . 1.420(4) yes C5 . C19 . 1.411(4) yes C6 . C7 . 1.427(4) yes C7 . C8 . 1.203(4) yes C8 . Si9 . 1.830(3) yes Si9 . C10 . 1.877(3) yes Si9 . C13 . 1.886(4) yes Si9 . C16 . 1.882(4) yes C10 . C11 . 1.535(5) yes C10 . C12 . 1.533(5) yes C10 . H101 . 0.962 no C11 . H111 . 0.936 no C11 . H112 . 0.970 no C11 . H113 . 0.973 no C12 . H121 . 0.939 no C12 . H122 . 0.949 no C12 . H123 . 0.951 no C13 . C14 . 1.466(5) yes C13 . C15 . 1.520(5) yes C13 . H131 . 0.996 no C14 . H141 . 1.024 no C14 . H142 . 0.997 no C14 . H143 . 0.996 no C15 . H151 . 0.956 no C15 . H152 . 0.962 no C15 . H153 . 0.965 no C16 . C17 . 1.494(6) yes C16 . C18 . 1.541(5) yes C16 . H161 . 1.005 no C17 . H171 . 0.963 no C17 . H172 . 0.981 no C17 . H173 . 0.964 no C18 . H181 . 0.961 no C18 . H182 . 0.959 no C18 . H183 . 0.960 no C19 . C20 . 1.385(4) yes C19 . H191 . 0.929 no C20 . C21 . 1.446(4) yes C20 . C26 . 1.420(4) yes C21 . C22 . 1.374(4) yes C21 . C23 . 1.439(4) yes C22 . H221 . 0.935 no C23 . C24 . 1.338(4) yes C23 . H231 . 0.957 no C24 . C25 . 1.424(4) yes C24 . H241 . 0.979 no C25 . C26 . 1.359(4) yes C25 . Br27 . 1.898(3) yes C26 . H261 . 0.926 no C28 . C29 . 1.202(4) yes C29 . Si30 . 1.836(3) yes Si30 . C31 . 1.883(4) yes Si30 . C34 . 1.871(4) yes Si30 . C37 . 1.874(4) yes C31 . C32 . 1.543(5) yes C31 . C33 . 1.510(6) yes C31 . H311 . 0.971 no C32 . H321 . 0.935 no C32 . H322 . 0.967 no C32 . H323 . 0.950 no C33 . H331 . 0.962 no C33 . H332 . 0.937 no C33 . H333 . 0.957 no C34 . C35 . 1.543(6) yes C34 . C36 . 1.525(6) yes C34 . H341 . 0.970 no C35 . H351 . 0.956 no C35 . H352 . 0.942 no C35 . H353 . 0.963 no C36 . H361 . 0.943 no C36 . H362 . 1.002 no C36 . H363 . 0.959 no C37 . C39 . 1.492(6) yes C37 . C9 . 1.359(7) yes C37 . H371 . 1.057 no C39 . H391 . 0.972 no C39 . H392 . 0.940 no C39 . H393 . 0.949 no C40 . C41 . 1.384(4) yes C40 . H401 . 0.938 no C41 . C42 . 1.445(4) yes C41 . C47 . 1.424(4) yes C42 . C43 . 1.381(4) yes C42 . C44 . 1.442(4) yes C43 . H431 . 0.924 no C44 . C45 . 1.337(4) yes C44 . H441 . 0.949 no C45 . C46 . 1.431(4) yes C45 . Br48 . 1.898(3) yes C46 . C47 . 1.346(4) yes C46 . H461 . 1.015 no C47 . H471 . 0.949 no C9 . H91 . 1.025 no C9 . H92 . 0.999 no C9 . H93 . 0.980 no 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 C2 . C1 . C6 . 119.9(2) yes C2 . C1 . C43 . 118.6(2) yes C6 . C1 . C43 . 121.5(2) yes C1 . C2 . C3 . 119.3(2) yes C1 . C2 . C40 . 118.5(3) yes C3 . C2 . C40 . 122.3(2) yes C2 . C3 . C4 . 121.2(2) yes C2 . C3 . C28 . 119.2(3) yes C4 . C3 . C28 . 119.6(2) yes C3 . C4 . C5 . 119.3(2) yes C3 . C4 . C22 . 122.2(2) yes C5 . C4 . C22 . 118.5(2) yes C4 . C5 . C6 . 119.5(2) yes C4 . C5 . C19 . 118.4(2) yes C6 . C5 . C19 . 122.0(2) yes C5 . C6 . C1 . 120.8(2) yes C5 . C6 . C7 . 120.0(2) yes C1 . C6 . C7 . 119.2(2) yes C6 . C7 . C8 . 178.1(3) yes C7 . C8 . Si9 . 177.7(3) yes C8 . Si9 . C10 . 107.29(14) yes C8 . Si9 . C13 . 106.20(15) yes C10 . Si9 . C13 . 109.05(15) yes C8 . Si9 . C16 . 106.75(15) yes C10 . Si9 . C16 . 109.78(16) yes C13 . Si9 . C16 . 117.28(18) yes Si9 . C10 . C11 . 112.6(2) yes Si9 . C10 . C12 . 111.6(2) yes C11 . C10 . C12 . 109.2(3) yes Si9 . C10 . H101 . 109.2 no C11 . C10 . H101 . 107.0 no C12 . C10 . H101 . 107.0 no C10 . C11 . H111 . 113.5 no C10 . C11 . H112 . 113.3 no H111 . C11 . H112 . 110.2 no C10 . C11 . H113 . 107.4 no H111 . C11 . H113 . 106.6 no H112 . C11 . H113 . 105.3 no C10 . C12 . H121 . 110.2 no C10 . C12 . H122 . 110.3 no H121 . C12 . H122 . 109.6 no C10 . C12 . H123 . 107.8 no H121 . C12 . H123 . 110.4 no H122 . C12 . H123 . 108.6 no Si9 . C13 . C14 . 115.4(3) yes Si9 . C13 . C15 . 114.6(3) yes C14 . C13 . C15 . 112.6(4) yes Si9 . C13 . H131 . 102.8 no C14 . C13 . H131 . 104.4 no C15 . C13 . H131 . 105.5 no C13 . C14 . H141 . 109.8 no C13 . C14 . H142 . 109.9 no H141 . C14 . H142 . 107.8 no C13 . C14 . H143 . 111.3 no H141 . C14 . H143 . 107.9 no H142 . C14 . H143 . 110.0 no C13 . C15 . H151 . 111.5 no C13 . C15 . H152 . 109.7 no H151 . C15 . H152 . 109.3 no C13 . C15 . H153 . 108.8 no H151 . C15 . H153 . 109.9 no H152 . C15 . H153 . 107.5 no Si9 . C16 . C17 . 115.2(3) yes Si9 . C16 . C18 . 111.9(3) yes C17 . C16 . C18 . 112.5(3) yes Si9 . C16 . H161 . 106.6 no C17 . C16 . H161 . 103.8 no C18 . C16 . H161 . 105.9 no C16 . C17 . H171 . 111.7 no C16 . C17 . H172 . 111.0 no H171 . C17 . H172 . 105.2 no C16 . C17 . H173 . 110.4 no H171 . C17 . H173 . 109.6 no H172 . C17 . H173 . 108.7 no C16 . C18 . H181 . 109.1 no C16 . C18 . H182 . 110.8 no H181 . C18 . H182 . 107.9 no C16 . C18 . H183 . 109.0 no H181 . C18 . H183 . 108.6 no H182 . C18 . H183 . 111.4 no C5 . C19 . C20 . 122.4(2) yes C5 . C19 . H191 . 117.7 no C20 . C19 . H191 . 119.9 no C19 . C20 . C21 . 118.6(3) yes C19 . C20 . C26 . 122.5(3) yes C21 . C20 . C26 . 118.9(2) yes C20 . C21 . C22 . 119.6(3) yes C20 . C21 . C23 . 117.3(3) yes C22 . C21 . C23 . 123.2(3) yes C4 . C22 . C21 . 122.4(2) yes C4 . C22 . H221 . 117.9 no C21 . C22 . H221 . 119.7 no C21 . C23 . C24 . 122.6(3) yes C21 . C23 . H231 . 117.5 no C24 . C23 . H231 . 119.9 no C23 . C24 . C25 . 119.0(3) yes C23 . C24 . H241 . 120.3 no C25 . C24 . H241 . 120.7 no C24 . C25 . C26 . 122.0(3) yes C24 . C25 . Br27 . 117.9(2) yes C26 . C25 . Br27 . 120.1(2) yes C20 . C26 . C25 . 120.2(3) yes C20 . C26 . H261 . 120.6 no C25 . C26 . H261 . 119.2 no C3 . C28 . C29 . 178.3(3) yes C28 . C29 . Si30 . 173.5(3) yes C29 . Si30 . C31 . 106.21(15) yes C29 . Si30 . C34 . 106.62(15) yes C31 . Si30 . C34 . 110.08(18) yes C29 . Si30 . C37 . 108.92(16) yes C31 . Si30 . C37 . 113.1(2) yes C34 . Si30 . C37 . 111.6(2) yes Si30 . C31 . C32 . 113.8(3) yes Si30 . C31 . C33 . 113.0(3) yes C32 . C31 . C33 . 111.7(4) yes Si30 . C31 . H311 . 105.1 no C32 . C31 . H311 . 106.8 no C33 . C31 . H311 . 105.6 no C31 . C32 . H321 . 111.2 no C31 . C32 . H322 . 110.7 no H321 . C32 . H322 . 109.9 no C31 . C32 . H323 . 109.5 no H321 . C32 . H323 . 107.7 no H322 . C32 . H323 . 107.7 no C31 . C33 . H331 . 110.1 no C31 . C33 . H332 . 111.0 no H331 . C33 . H332 . 106.1 no C31 . C33 . H333 . 112.8 no H331 . C33 . H333 . 105.7 no H332 . C33 . H333 . 110.8 no Si30 . C34 . C35 . 111.5(3) yes Si30 . C34 . C36 . 113.7(3) yes C35 . C34 . C36 . 109.3(4) yes Si30 . C34 . H341 . 107.4 no C35 . C34 . H341 . 105.2 no C36 . C34 . H341 . 109.5 no C34 . C35 . H351 . 108.9 no C34 . C35 . H352 . 109.0 no H351 . C35 . H352 . 110.1 no C34 . C35 . H353 . 110.4 no H351 . C35 . H353 . 108.6 no H352 . C35 . H353 . 109.8 no C34 . C36 . H361 . 113.8 no C34 . C36 . H362 . 110.4 no H361 . C36 . H362 . 105.2 no C34 . C36 . H363 . 114.4 no H361 . C36 . H363 . 107.5 no H362 . C36 . H363 . 104.7 no Si30 . C37 . C39 . 114.0(3) yes Si30 . C37 . C9 . 121.3(3) yes C39 . C37 . C9 . 123.7(4) yes Si30 . C37 . H371 . 94.7 no C39 . C37 . H371 . 93.8 no C9 . C37 . H371 . 92.0 no C37 . C39 . H391 . 110.8 no C37 . C39 . H392 . 112.7 no H391 . C39 . H392 . 107.1 no C37 . C39 . H393 . 109.0 no H391 . C39 . H393 . 108.2 no H392 . C39 . H393 . 108.9 no C2 . C40 . C41 . 122.8(3) yes C2 . C40 . H401 . 118.9 no C41 . C40 . H401 . 118.4 no C40 . C41 . C42 . 118.6(3) yes C40 . C41 . C47 . 123.5(3) yes C42 . C41 . C47 . 117.9(3) yes C41 . C42 . C43 . 119.5(3) yes C41 . C42 . C44 . 118.3(3) yes C43 . C42 . C44 . 122.2(3) yes C1 . C43 . C42 . 122.1(3) yes C1 . C43 . H431 . 118.6 no C42 . C43 . H431 . 119.3 no C42 . C44 . C45 . 120.0(3) yes C42 . C44 . H441 . 119.3 no C45 . C44 . H441 . 120.7 no C44 . C45 . C46 . 122.7(3) yes C44 . C45 . Br48 . 119.6(2) yes C46 . C45 . Br48 . 117.8(2) yes C45 . C46 . C47 . 118.5(3) yes C45 . C46 . H461 . 118.0 no C47 . C46 . H461 . 123.4 no C41 . C47 . C46 . 122.6(3) yes C41 . C47 . H471 . 119.1 no C46 . C47 . H471 . 118.3 no C37 . C9 . H91 . 108.3 no C37 . C9 . H92 . 111.9 no H91 . C9 . H92 . 107.6 no C37 . C9 . H93 . 108.8 no H91 . C9 . H93 . 109.0 no H92 . C9 . H93 . 111.2 no # Attachment '- 2-9-TIPS-Br-pentacene_120K.cif' data_2-9-TIPS-Br-pentacene_120K _database_code_depnum_ccdc_archive 'CCDC 734418' #TrackingRef '- 2-9-TIPS-Br-pentacene_120K.cif' _audit_creation_date 07-08-27 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title 'dc in P-1' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 10.5231(8) _cell_length_b 10.9713(8) _cell_length_c 17.445(2) _cell_angle_alpha 90.807(8) _cell_angle_beta 89.922(8) _cell_angle_gamma 91.961(6) _cell_volume 2012.6(3) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z 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' 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' 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' _cell_formula_units_Z 8 # Given Formula = C8.50 H13 Br0.50 Si0.50 # Dc = 1.12 Fooo = 828.00 Mu = 20.91 M = 676.77 # Found Formula = C11 H13 Br0.50 Si0.50 # Dc = 1.31 FOOO = 828.00 Mu = 21.03 M = 796.88 _chemical_formula_sum 'C11 H13 Br0.50 Si0.50' _chemical_formula_moiety 'C11 H13 Br0.50 Si0.50' _chemical_compound_source ? _chemical_formula_weight 199.22 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 120 _exptl_crystal_description prism _exptl_crystal_colour blue-black _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_max 0.15 _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 828 _exptl_absorpt_coefficient_mu 2.103 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min 0.84 _exptl_absorpt_correction_T_max 1.00 _diffrn_measurement_device_type 'Oxford Diffraction XCALIBUR' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Xcalibur, (Oxford Diffraction, 2002)' _computing_cell_refinement 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_structure_solution CIR92 _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 ? _diffrn_standards_number ? _diffrn_standards_decay_% ? _diffrn_ambient_temperature 120 _diffrn_reflns_number 25038 _reflns_number_total 11825 _diffrn_reflns_av_R_equivalents 0.080 # Number of reflections with Friedels Law is 11825 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 15126 _diffrn_reflns_theta_min 2.637 _diffrn_reflns_theta_max 32.960 _diffrn_measured_fraction_theta_max 0.782 _diffrn_reflns_theta_full 25.049 _diffrn_measured_fraction_theta_full 0.918 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _reflns_limit_h_min -16 _reflns_limit_h_max 15 _reflns_limit_k_min -16 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 26 _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 -0.68 _refine_diff_density_max 1.05 _refine_ls_number_reflns 4535 _refine_ls_number_restraints 0 _refine_ls_number_parameters 433 #_refine_ls_R_factor_ref 0.0489 _refine_ls_wR_factor_ref 0.0535 _refine_ls_goodness_of_fit_ref 1.0662 #_reflns_number_all 11800 _refine_ls_R_factor_all 0.1542 _refine_ls_wR_factor_all 0.0823 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.0\s(I) _reflns_number_gt 4535 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_gt 0.0535 _refine_ls_shift/su_max 0.000294 # 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: 6.58 -1.30 5.82 ; _publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ; _publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fih. ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; _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 absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. 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. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. North, A.C.T., Phillips, D.C. & Mathews, F.S., (1968). Acta Cryst, A24, 351-359. 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 _atom_site_attached_hydrogens C1 C 0.1234(4) 0.8180(4) 0.5756(3) 0.0127 1.0000 Uani . . . . . . C2 C 0.1033(5) 0.7980(4) 0.4943(3) 0.0149 1.0000 Uani . . . . . . C3 C 0.2006(5) 0.7477(4) 0.4491(3) 0.0131 1.0000 Uani . . . . . . C4 C 0.3193(5) 0.7220(4) 0.4811(3) 0.0151 1.0000 Uani . . . . . . C5 C 0.3408(5) 0.7429(4) 0.5617(3) 0.0110 1.0000 Uani . . . . . . C6 C 0.2422(5) 0.7901(4) 0.6077(3) 0.0151 1.0000 Uani . . . . . . C7 C 0.2627(5) 0.8027(5) 0.6888(3) 0.0169 1.0000 Uani . . . . . . C8 C 0.2897(5) 0.8049(5) 0.7548(3) 0.0181 1.0000 Uani . . . . . . C10 C 0.5106(5) 0.8432(5) 0.8627(3) 0.0234 1.0000 Uani . . . . . . C11 C 0.6070(6) 0.7832(6) 0.8105(4) 0.0313 1.0000 Uani . . . . . . C12 C 0.5590(6) 0.8491(6) 0.9458(4) 0.0363 1.0000 Uani . . . . . . C13 C 0.2359(6) 0.8612(6) 0.9210(3) 0.0293 1.0000 Uani . . . . . . C14 C 0.0994(6) 0.8105(7) 0.9209(4) 0.0439 1.0000 Uani . . . . . . Si15 Si 0.34281(14) 0.77777(13) 0.85332(8) 0.0187 1.0000 Uani . . . . . . C16 C 0.4588(5) 0.7132(4) 0.5932(3) 0.0132 1.0000 Uani . . . . . . C17 C 0.5544(5) 0.6665(4) 0.5488(3) 0.0125 1.0000 Uani . . . . . . C18 C 0.5348(5) 0.6481(5) 0.4678(3) 0.0188 1.0000 Uani . . . . . . C19 C 0.4194(5) 0.6747(5) 0.4366(3) 0.0145 1.0000 Uani . . . . . . C20 C 0.6372(5) 0.6011(5) 0.4232(3) 0.0168 1.0000 Uani . . . . . . C21 C 0.7478(5) 0.5754(4) 0.4567(3) 0.0190 1.0000 Uani . . . . . . C22 C 0.7691(5) 0.5929(4) 0.5365(3) 0.0166 1.0000 Uani . . . . . . C23 C 0.6758(5) 0.6383(5) 0.5806(3) 0.0173 1.0000 Uani . . . . . . Br24 Br 0.88271(5) 0.51490(5) 0.39629(4) 0.0227 1.0000 Uani . . . . . . C25 C 0.1771(5) 0.7210(4) 0.3697(3) 0.0130 1.0000 Uani . . . . . . C26 C 0.1541(5) 0.6950(5) 0.3039(3) 0.0219 1.0000 Uani . . . . . . Si27 Si 0.11675(14) 0.65044(13) 0.20460(8) 0.0200 1.0000 Uani . . . . . . C28 C -0.0594(6) 0.6646(5) 0.1889(3) 0.0252 1.0000 Uani . . . . . . C51 C -0.1205(6) 0.7640(6) 0.2379(4) 0.0349 1.0000 Uani . . . . . . C30 C -0.0927(7) 0.6800(7) 0.1035(4) 0.0382 1.0000 Uani . . . . . . C33 C -0.0138(5) 0.8283(4) 0.4638(3) 0.0150 1.0000 Uani . . . . . . C49 C -0.1107(5) 0.8748(4) 0.5078(3) 0.0149 1.0000 Uani . . . . . . C35 C -0.0911(5) 0.8926(4) 0.5889(3) 0.0130 1.0000 Uani . . . . . . C36 C 0.0246(5) 0.8637(4) 0.6201(3) 0.0148 1.0000 Uani . . . . . . C37 C -0.1927(5) 0.9384(5) 0.6338(3) 0.0182 1.0000 Uani . . . . . . C50 C -0.3034(5) 0.9637(5) 0.6003(3) 0.0184 1.0000 Uani . . . . . . C46 C -0.3234(5) 0.9494(5) 0.5214(4) 0.0208 1.0000 Uani . . . . . . C40 C -0.2295(5) 0.9050(5) 0.4754(3) 0.0189 1.0000 Uani . . . . . . Br41 Br -0.44034(5) 1.02539(5) 0.65884(3) 0.0234 1.0000 Uani . . . . . . C29 C 0.1854(8) 0.8876(6) 0.1505(4) 0.0421 1.0000 Uani . . . . . . C34 C 0.3725(7) 0.5323(6) 0.7968(4) 0.0362 1.0000 Uani . . . . . . C38 C 0.3268(6) 0.6070(5) 0.8654(3) 0.0260 1.0000 Uani . . . . . . C39 C 0.1512(6) 0.4429(6) 0.1081(3) 0.0325 1.0000 Uani . . . . . . C41 C 0.0934(6) 0.4003(5) 0.2448(4) 0.0293 1.0000 Uani . . . . . . C45 C 0.1646(5) 0.4878(5) 0.1911(3) 0.0246 1.0000 Uani . . . . . . C47 C 0.2389(7) 0.9973(5) 0.9052(4) 0.0390 1.0000 Uani . . . . . . C48 C 0.3868(7) 0.5638(6) 0.9385(4) 0.0373 1.0000 Uani . . . . . . C9 C 0.2168(6) 0.7533(5) 0.1406(3) 0.0296 1.0000 Uani . . . . . . C15 C 0.3598(6) 0.7349(7) 0.1514(4) 0.0417 1.0000 Uani . . . . . . H101 H 0.5069 0.9283 0.8469 0.0338 1.0000 Uiso R . . . . . H111 H 0.5794 0.7835 0.7585 0.0518 1.0000 Uiso R . . . . . H112 H 0.6880 0.8259 0.8145 0.0521 1.0000 Uiso R . . . . . H113 H 0.6163 0.7005 0.8256 0.0518 1.0000 Uiso R . . . . . H121 H 0.4977 0.8887 0.9774 0.0547 1.0000 Uiso R . . . . . H122 H 0.6397 0.8932 0.9488 0.0550 1.0000 Uiso R . . . . . H123 H 0.5691 0.7676 0.9626 0.0547 1.0000 Uiso R . . . . . H131 H 0.2701 0.8513 0.9730 0.0389 1.0000 Uiso R . . . . . H141 H 0.0499 0.8549 0.9578 0.0649 1.0000 Uiso R . . . . . H142 H 0.0982 0.7262 0.9342 0.0649 1.0000 Uiso R . . . . . H143 H 0.0627 0.8193 0.8710 0.0648 1.0000 Uiso R . . . . . H161 H 0.4731 0.7260 0.6454 0.0198 1.0000 Uiso R . . . . . H191 H 0.4072 0.6612 0.3845 0.0171 1.0000 Uiso R . . . . . H201 H 0.6263 0.5885 0.3706 0.0202 1.0000 Uiso R . . . . . H221 H 0.8470 0.5738 0.5577 0.0279 1.0000 Uiso R . . . . . H231 H 0.6896 0.6500 0.6326 0.0235 1.0000 Uiso R . . . . . H281 H -0.0983 0.5868 0.2055 0.0289 1.0000 Uiso R . . . . . H511 H -0.2084 0.7702 0.2240 0.0549 1.0000 Uiso R . . . . . H512 H -0.0772 0.8408 0.2291 0.0547 1.0000 Uiso R . . . . . H513 H -0.1136 0.7446 0.2911 0.0550 1.0000 Uiso R . . . . . H301 H -0.1833 0.6832 0.0984 0.0600 1.0000 Uiso R . . . . . H302 H -0.0540 0.7536 0.0850 0.0598 1.0000 Uiso R . . . . . H303 H -0.0618 0.6122 0.0741 0.0599 1.0000 Uiso R . . . . . H331 H -0.0268 0.8168 0.4111 0.0187 1.0000 Uiso R . . . . . H361 H 0.0369 0.8755 0.6719 0.0189 1.0000 Uiso R . . . . . H371 H -0.1828 0.9510 0.6859 0.0239 1.0000 Uiso R . . . . . H461 H -0.4019 0.9680 0.5001 0.0206 1.0000 Uiso R . . . . . H401 H -0.2419 0.8944 0.4230 0.0215 1.0000 Uiso R . . . . . H291 H 0.2357 0.9350 0.1153 0.0602 1.0000 Uiso R . . . . . H292 H 0.2054 0.9131 0.2021 0.0600 1.0000 Uiso R . . . . . H293 H 0.0972 0.8995 0.1407 0.0598 1.0000 Uiso R . . . . . H341 H 0.3582 0.4470 0.8064 0.0529 1.0000 Uiso R . . . . . H342 H 0.4616 0.5482 0.7892 0.0529 1.0000 Uiso R . . . . . H343 H 0.3270 0.5532 0.7517 0.0528 1.0000 Uiso R . . . . . H381 H 0.2348 0.5888 0.8707 0.0340 1.0000 Uiso R . . . . . H391 H 0.1789 0.3604 0.1046 0.0540 1.0000 Uiso R . . . . . H392 H 0.2022 0.4930 0.0748 0.0541 1.0000 Uiso R . . . . . H393 H 0.0642 0.4455 0.0931 0.0538 1.0000 Uiso R . . . . . H411 H 0.1260 0.3196 0.2384 0.0508 1.0000 Uiso R . . . . . H412 H 0.1045 0.4273 0.2968 0.0508 1.0000 Uiso R . . . . . H413 H 0.0045 0.3984 0.2323 0.0508 1.0000 Uiso R . . . . . H451 H 0.2546 0.4855 0.2049 0.0318 1.0000 Uiso R . . . . . H471 H 0.3246 1.0293 0.9095 0.0659 1.0000 Uiso R . . . . . H472 H 0.1849 1.0372 0.9417 0.0659 1.0000 Uiso R . . . . . H473 H 0.2080 1.0096 0.8542 0.0661 1.0000 Uiso R . . . . . H481 H 0.3627 0.4795 0.9465 0.0602 1.0000 Uiso R . . . . . H482 H 0.3588 0.6127 0.9810 0.0597 1.0000 Uiso R . . . . . H483 H 0.4771 0.5717 0.9332 0.0597 1.0000 Uiso R . . . . . H91 H 0.1962 0.7294 0.0874 0.0369 1.0000 Uiso R . . . . . H151 H 0.4074 0.7882 0.1178 0.0681 1.0000 Uiso R . . . . . H152 H 0.3837 0.7533 0.2035 0.0679 1.0000 Uiso R . . . . . H153 H 0.3793 0.6520 0.1394 0.0678 1.0000 Uiso R . . . . . 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 C1 0.012(2) 0.014(2) 0.012(2) 0.0050(19) 0.004(2) -0.0042(19) C2 0.018(3) 0.010(2) 0.016(3) 0.000(2) 0.003(2) -0.005(2) C3 0.019(3) 0.013(2) 0.008(2) 0.0021(19) -0.001(2) -0.001(2) C4 0.014(2) 0.013(2) 0.018(3) -0.001(2) -0.001(2) 0.001(2) C5 0.011(3) 0.009(2) 0.013(3) 0.0038(19) 0.000(2) -0.0057(19) C6 0.017(3) 0.013(2) 0.015(3) 0.0040(19) -0.001(2) -0.005(2) C7 0.017(3) 0.015(2) 0.018(3) -0.002(2) 0.000(2) -0.002(2) C8 0.015(2) 0.023(3) 0.016(3) 0.003(2) 0.001(2) 0.001(2) C10 0.028(3) 0.017(2) 0.025(3) 0.002(2) -0.004(2) -0.001(2) C11 0.031(3) 0.031(3) 0.032(4) -0.004(3) -0.003(3) 0.001(3) C12 0.031(3) 0.044(4) 0.033(4) -0.006(3) -0.004(3) -0.011(3) C13 0.040(3) 0.034(3) 0.015(3) -0.003(2) -0.002(3) 0.007(3) C14 0.029(3) 0.061(4) 0.041(4) -0.007(3) 0.008(3) -0.004(3) Si15 0.0249(7) 0.0190(7) 0.0121(7) 0.0005(5) -0.0039(6) 0.0005(6) C16 0.017(3) 0.012(2) 0.011(2) 0.0016(19) -0.002(2) -0.0042(19) C17 0.011(2) 0.013(2) 0.013(2) -0.0023(19) -0.002(2) -0.0012(18) C18 0.016(3) 0.010(2) 0.030(3) 0.000(2) 0.001(2) -0.005(2) C19 0.013(3) 0.016(2) 0.014(3) 0.001(2) -0.005(2) -0.005(2) C20 0.016(3) 0.016(2) 0.018(3) 0.003(2) -0.001(2) -0.006(2) C21 0.020(3) 0.008(2) 0.029(3) 0.000(2) 0.004(3) -0.002(2) C22 0.020(3) 0.014(2) 0.015(3) -0.001(2) -0.003(2) -0.003(2) C23 0.018(3) 0.017(2) 0.017(3) 0.000(2) -0.003(2) 0.001(2) Br24 0.0172(3) 0.0207(3) 0.0301(4) 0.0001(3) 0.0040(3) 0.0010(2) C25 0.010(3) 0.011(2) 0.018(3) -0.001(2) -0.003(2) -0.0023(19) C26 0.019(3) 0.022(3) 0.024(3) -0.004(2) -0.002(2) -0.007(2) Si27 0.0246(7) 0.0222(7) 0.0130(7) -0.0015(6) -0.0019(6) -0.0028(6) C28 0.032(3) 0.024(3) 0.020(3) 0.003(2) -0.007(2) 0.001(2) C51 0.036(4) 0.036(3) 0.032(4) 0.002(3) -0.008(3) 0.006(3) C30 0.041(4) 0.047(4) 0.026(3) -0.003(3) -0.011(3) 0.002(3) C33 0.016(3) 0.015(2) 0.013(3) 0.004(2) -0.002(2) -0.006(2) C49 0.018(3) 0.010(2) 0.016(3) 0.002(2) 0.000(2) -0.002(2) C35 0.017(3) 0.011(2) 0.011(2) 0.0027(19) 0.000(2) 0.000(2) C36 0.017(3) 0.016(2) 0.011(3) 0.001(2) 0.001(2) -0.001(2) C37 0.018(3) 0.018(2) 0.019(3) -0.001(2) 0.002(2) -0.003(2) C50 0.016(3) 0.022(3) 0.018(3) 0.003(2) -0.001(2) -0.001(2) C46 0.001(2) 0.016(3) 0.046(4) 0.006(3) 0.001(2) -0.0025(18) C40 0.016(3) 0.015(3) 0.025(3) 0.001(2) 0.002(2) -0.004(2) Br41 0.0188(3) 0.0244(3) 0.0270(3) -0.0014(3) 0.0036(3) 0.0025(2) C29 0.066(5) 0.031(3) 0.027(3) 0.002(3) 0.008(3) -0.014(3) C34 0.049(4) 0.028(3) 0.032(3) -0.008(3) -0.003(3) -0.005(3) C38 0.035(3) 0.024(3) 0.019(3) 0.003(2) -0.005(2) -0.008(2) C39 0.042(3) 0.034(3) 0.021(3) -0.006(2) -0.003(3) -0.001(3) C41 0.036(3) 0.025(3) 0.027(3) 0.000(2) 0.005(3) 0.006(2) C45 0.023(3) 0.026(3) 0.024(3) -0.006(2) 0.000(2) 0.002(2) C47 0.052(4) 0.028(3) 0.038(4) -0.008(3) -0.007(3) 0.016(3) C48 0.054(4) 0.025(3) 0.032(3) 0.006(3) -0.010(3) -0.010(3) C9 0.045(4) 0.031(3) 0.012(3) -0.003(2) -0.003(2) -0.011(3) C15 0.036(4) 0.050(4) 0.038(4) -0.001(3) 0.005(3) -0.019(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.5193(10) 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 C1 . C2 . 1.448(7) yes C1 . C6 . 1.415(7) yes C1 . C36 . 1.399(6) yes C2 . C3 . 1.413(7) yes C2 . C33 . 1.396(8) yes C3 . C4 . 1.408(8) yes C3 . C25 . 1.431(7) yes C4 . C5 . 1.438(7) yes C4 . C19 . 1.416(7) yes C5 . C6 . 1.418(7) yes C5 . C16 . 1.409(7) yes C6 . C7 . 1.436(7) yes C7 . C8 . 1.186(7) yes C8 . Si15 . 1.839(6) yes C10 . C11 . 1.523(8) yes C10 . C12 . 1.537(9) yes C10 . Si15 . 1.889(6) yes C10 . H101 . 0.979 no C11 . H111 . 0.953 no C11 . H112 . 0.961 no C11 . H113 . 0.957 no C12 . H121 . 0.959 no C12 . H122 . 0.964 no C12 . H123 . 0.954 no C13 . C14 . 1.523(9) yes C13 . Si15 . 1.880(6) yes C13 . C47 . 1.521(8) yes C13 . H131 . 0.986 no C14 . H141 . 0.965 no C14 . H142 . 0.956 no C14 . H143 . 0.960 no Si15 . C38 . 1.890(6) yes C16 . C17 . 1.377(6) yes C16 . H161 . 0.931 no C17 . C18 . 1.439(8) yes C17 . C23 . 1.438(7) yes C18 . C19 . 1.374(8) yes C18 . C20 . 1.434(7) yes C19 . H191 . 0.926 no C20 . C21 . 1.343(8) yes C20 . H201 . 0.931 no C21 . C22 . 1.420(8) yes C21 . Br24 . 1.900(5) yes C22 . C23 . 1.350(7) yes C22 . H221 . 0.931 no C23 . H231 . 0.924 no C25 . C26 . 1.201(8) yes C26 . Si27 . 1.834(6) yes Si27 . C28 . 1.886(6) yes Si27 . C45 . 1.882(6) yes Si27 . C9 . 1.893(6) yes C28 . C51 . 1.534(8) yes C28 . C30 . 1.544(9) yes C28 . H281 . 0.981 no C51 . H511 . 0.962 no C51 . H512 . 0.958 no C51 . H513 . 0.959 no C30 . H301 . 0.959 no C30 . H302 . 0.952 no C30 . H303 . 0.963 no C33 . C49 . 1.383(7) yes C33 . H331 . 0.936 no C49 . C35 . 1.441(7) yes C49 . C40 . 1.423(8) yes C35 . C36 . 1.382(7) yes C35 . C37 . 1.425(6) yes C36 . H361 . 0.920 no C37 . C50 . 1.344(8) yes C37 . H371 . 0.922 no C50 . C46 . 1.398(8) yes C50 . Br41 . 1.903(5) yes C46 . C40 . 1.370(7) yes C46 . H461 . 0.936 no C40 . H401 . 0.929 no C29 . C9 . 1.528(9) yes C29 . H291 . 0.958 no C29 . H292 . 0.961 no C29 . H293 . 0.957 no C34 . C38 . 1.527(8) yes C34 . H341 . 0.960 no C34 . H342 . 0.957 no C34 . H343 . 0.955 no C38 . C48 . 1.514(9) yes C38 . H381 . 0.987 no C39 . C45 . 1.529(7) yes C39 . H391 . 0.960 no C39 . H392 . 0.956 no C39 . H393 . 0.954 no C41 . C45 . 1.528(8) yes C41 . H411 . 0.966 no C41 . H412 . 0.957 no C41 . H413 . 0.960 no C45 . H451 . 0.979 no C47 . H471 . 0.959 no C47 . H472 . 0.964 no C47 . H473 . 0.960 no C48 . H481 . 0.963 no C48 . H482 . 0.960 no C48 . H483 . 0.956 no C9 . C15 . 1.537(9) yes C9 . H91 . 0.983 no C15 . H151 . 0.962 no C15 . H152 . 0.960 no C15 . H153 . 0.959 no 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 C2 . C1 . C6 . 118.9(4) yes C2 . C1 . C36 . 119.0(5) yes C6 . C1 . C36 . 122.1(5) yes C1 . C2 . C3 . 119.6(5) yes C1 . C2 . C33 . 117.8(5) yes C3 . C2 . C33 . 122.6(5) yes C2 . C3 . C4 . 121.1(4) yes C2 . C3 . C25 . 119.3(5) yes C4 . C3 . C25 . 119.6(4) yes C3 . C4 . C5 . 119.7(4) yes C3 . C4 . C19 . 122.1(5) yes C5 . C4 . C19 . 118.2(5) yes C4 . C5 . C6 . 119.4(5) yes C4 . C5 . C16 . 118.9(5) yes C6 . C5 . C16 . 121.7(5) yes C5 . C6 . C1 . 121.3(5) yes C5 . C6 . C7 . 118.4(5) yes C1 . C6 . C7 . 120.2(4) yes C6 . C7 . C8 . 173.2(6) yes C7 . C8 . Si15 . 168.6(5) yes C11 . C10 . C12 . 110.5(5) yes C11 . C10 . Si15 . 114.5(4) yes C12 . C10 . Si15 . 113.4(4) yes C11 . C10 . H101 . 106.7 no C12 . C10 . H101 . 105.2 no Si15 . C10 . H101 . 105.7 no C10 . C11 . H111 . 110.7 no C10 . C11 . H112 . 110.0 no H111 . C11 . H112 . 109.2 no C10 . C11 . H113 . 109.3 no H111 . C11 . H113 . 108.7 no H112 . C11 . H113 . 109.0 no C10 . C12 . H121 . 109.1 no C10 . C12 . H122 . 110.6 no H121 . C12 . H122 . 109.9 no C10 . C12 . H123 . 108.1 no H121 . C12 . H123 . 109.9 no H122 . C12 . H123 . 109.3 no C14 . C13 . Si15 . 113.4(4) yes C14 . C13 . C47 . 110.3(6) yes Si15 . C13 . C47 . 111.4(4) yes C14 . C13 . H131 . 107.5 no Si15 . C13 . H131 . 106.9 no C47 . C13 . H131 . 107.0 no C13 . C14 . H141 . 109.6 no C13 . C14 . H142 . 109.5 no H141 . C14 . H142 . 109.2 no C13 . C14 . H143 . 109.8 no H141 . C14 . H143 . 108.9 no H142 . C14 . H143 . 109.9 no C10 . Si15 . C13 . 109.3(3) yes C10 . Si15 . C8 . 107.5(2) yes C13 . Si15 . C8 . 108.2(3) yes C10 . Si15 . C38 . 114.6(3) yes C13 . Si15 . C38 . 111.7(3) yes C8 . Si15 . C38 . 105.1(2) yes C5 . C16 . C17 . 121.9(5) yes C5 . C16 . H161 . 119.3 no C17 . C16 . H161 . 118.8 no C16 . C17 . C18 . 119.6(5) yes C16 . C17 . C23 . 121.9(5) yes C18 . C17 . C23 . 118.4(4) yes C17 . C18 . C19 . 119.1(5) yes C17 . C18 . C20 . 118.1(5) yes C19 . C18 . C20 . 122.8(5) yes C4 . C19 . C18 . 122.3(5) yes C4 . C19 . H191 . 119.2 no C18 . C19 . H191 . 118.5 no C18 . C20 . C21 . 120.4(5) yes C18 . C20 . H201 . 119.3 no C21 . C20 . H201 . 120.3 no C20 . C21 . C22 . 122.4(5) yes C20 . C21 . Br24 . 119.7(4) yes C22 . C21 . Br24 . 117.9(4) yes C21 . C22 . C23 . 119.2(5) yes C21 . C22 . H221 . 119.9 no C23 . C22 . H221 . 120.9 no C17 . C23 . C22 . 121.4(5) yes C17 . C23 . H231 . 119.2 no C22 . C23 . H231 . 119.4 no C3 . C25 . C26 . 177.4(5) yes C25 . C26 . Si27 . 178.1(5) yes C26 . Si27 . C28 . 108.6(3) yes C26 . Si27 . C45 . 107.2(3) yes C28 . Si27 . C45 . 110.9(3) yes C26 . Si27 . C9 . 107.1(2) yes C28 . Si27 . C9 . 113.0(3) yes C45 . Si27 . C9 . 109.7(3) yes Si27 . C28 . C51 . 114.5(4) yes Si27 . C28 . C30 . 112.3(4) yes C51 . C28 . C30 . 110.4(5) yes Si27 . C28 . H281 . 105.4 no C51 . C28 . H281 . 106.1 no C30 . C28 . H281 . 107.7 no C28 . C51 . H511 . 109.8 no C28 . C51 . H512 . 109.5 no H511 . C51 . H512 . 108.9 no C28 . C51 . H513 . 109.7 no H511 . C51 . H513 . 110.0 no H512 . C51 . H513 . 109.0 no C28 . C30 . H301 . 108.9 no C28 . C30 . H302 . 109.8 no H301 . C30 . H302 . 109.5 no C28 . C30 . H303 . 109.6 no H301 . C30 . H303 . 109.9 no H302 . C30 . H303 . 109.1 no C2 . C33 . C49 . 123.0(5) yes C2 . C33 . H331 . 118.2 no C49 . C33 . H331 . 118.8 no C33 . C49 . C35 . 119.0(5) yes C33 . C49 . C40 . 122.0(5) yes C35 . C49 . C40 . 119.0(5) yes C49 . C35 . C36 . 118.8(4) yes C49 . C35 . C37 . 118.4(5) yes C36 . C35 . C37 . 122.8(5) yes C1 . C36 . C35 . 122.4(5) yes C1 . C36 . H361 . 119.0 no C35 . C36 . H361 . 118.6 no C35 . C37 . C50 . 120.0(5) yes C35 . C37 . H371 . 120.3 no C50 . C37 . H371 . 119.6 no C37 . C50 . C46 . 122.4(5) yes C37 . C50 . Br41 . 120.9(4) yes C46 . C50 . Br41 . 116.7(4) yes C50 . C46 . C40 . 120.1(5) yes C50 . C46 . H461 . 120.0 no C40 . C46 . H461 . 119.9 no C49 . C40 . C46 . 120.0(6) yes C49 . C40 . H401 . 119.1 no C46 . C40 . H401 . 120.9 no C9 . C29 . H291 . 109.0 no C9 . C29 . H292 . 108.7 no H291 . C29 . H292 . 109.6 no C9 . C29 . H293 . 110.9 no H291 . C29 . H293 . 109.1 no H292 . C29 . H293 . 109.4 no C38 . C34 . H341 . 109.6 no C38 . C34 . H342 . 109.5 no H341 . C34 . H342 . 108.8 no C38 . C34 . H343 . 110.0 no H341 . C34 . H343 . 109.1 no H342 . C34 . H343 . 109.8 no C34 . C38 . Si15 . 114.6(4) yes C34 . C38 . C48 . 110.4(5) yes Si15 . C38 . C48 . 113.1(4) yes C34 . C38 . H381 . 106.8 no Si15 . C38 . H381 . 105.4 no C48 . C38 . H381 . 105.8 no C45 . C39 . H391 . 108.8 no C45 . C39 . H392 . 110.5 no H391 . C39 . H392 . 109.2 no C45 . C39 . H393 . 109.1 no H391 . C39 . H393 . 109.7 no H392 . C39 . H393 . 109.5 no C45 . C41 . H411 . 109.3 no C45 . C41 . H412 . 109.8 no H411 . C41 . H412 . 109.7 no C45 . C41 . H413 . 109.1 no H411 . C41 . H413 . 109.5 no H412 . C41 . H413 . 109.4 no C39 . C45 . C41 . 110.2(5) yes C39 . C45 . Si27 . 112.7(4) yes C41 . C45 . Si27 . 112.7(4) yes C39 . C45 . H451 . 107.6 no C41 . C45 . H451 . 106.5 no Si27 . C45 . H451 . 106.7 no C13 . C47 . H471 . 109.5 no C13 . C47 . H472 . 109.0 no H471 . C47 . H472 . 110.3 no C13 . C47 . H473 . 108.8 no H471 . C47 . H473 . 109.7 no H472 . C47 . H473 . 109.6 no C38 . C48 . H481 . 109.6 no C38 . C48 . H482 . 109.4 no H481 . C48 . H482 . 109.9 no C38 . C48 . H483 . 108.3 no H481 . C48 . H483 . 109.3 no H482 . C48 . H483 . 110.3 no C29 . C9 . Si27 . 112.4(4) yes C29 . C9 . C15 . 111.1(5) yes Si27 . C9 . C15 . 111.9(4) yes C29 . C9 . H91 . 107.3 no Si27 . C9 . H91 . 106.8 no C15 . C9 . H91 . 107.0 no C9 . C15 . H151 . 109.5 no C9 . C15 . H152 . 110.0 no H151 . C15 . H152 . 109.1 no C9 . C15 . H153 . 109.9 no H151 . C15 . H153 . 109.0 no H152 . C15 . H153 . 109.3 no