# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2010 data_global _journal_coden_Cambridge 440 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Gregory Franc' ; ? # Address for author 1 ; ; ? # Footnote for author 1 ; 'Elena Badetti' ; ? # Address 2 ; ; ? # Footnote 2 ; 'Carine Duhayon' '' '' 'Yannick Coppel' '' '' 'Cedric-Olivier Turrin' '' '' 'Jean-Pierre Majoral' '' '' 'Rosa-Maria Sebastian' '' '' 'Anne-Marie Caminade' '' '' _publ_contact_author_name 'Anne-Marie Caminade, Anne-Marie' _publ_contact_author_email caminade@lcc-toulouse.fr _publ_section_title ; An efficient synthesis combining phosphorus dendrimers and 15-membered triolefinic azamacrocycles: towards the stabilization of Platinum nanoparticles ; _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_name_full ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ? _publ_contact_author_address ; ; # 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 ; ; _publ_requested_category CO # choose from: FI FM FO CI CM CO AD # Attachment '- GF280306.cif' data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 751820' _audit_creation_date 06-03-30 _audit_creation_method CRYSTALS_ver_12.51 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.265(5) _cell_length_b 12.133(5) _cell_length_c 15.070(5) _cell_angle_alpha 101.754(5) _cell_angle_beta 96.690(5) _cell_angle_gamma 93.917(5) _cell_volume 1108.9(11) _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' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 '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' _cell_formula_units_Z 1 # Given Formula = C42 H62 Br2 N2 O4 S2 # Dc = 1.32 Fooo = 464.00 Mu = 19.62 M = 441.45 # Found Formula = C42 H64 Br2 N2 O4 S2 # Dc = 1.33 FOOO = 464.00 Mu = 19.62 M = 442.46 _chemical_formula_sum 'C42 H64 Br2 N2 O4 S2' _chemical_formula_moiety 'C42 H64 Br2 N2 O4 S2' _chemical_compound_source ? _chemical_formula_weight 884.92 _cell_measurement_reflns_used 4000 _cell_measurement_theta_min 3 _cell_measurement_theta_max 24 _cell_measurement_temperature 180 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_min 0.13 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_max 0.32 _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 1.962 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.66 _exptl_absorpt_correction_T_max 0.78 _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 '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Xcalibur, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_cell_refinement 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _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 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 180 _diffrn_reflns_number 10430 _reflns_number_total 5890 _diffrn_reflns_av_R_equivalents 0.025 # Number of reflections with Friedels Law is 5890 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 5930 _diffrn_reflns_theta_min 2.946 _diffrn_reflns_theta_max 29.057 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.023 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _reflns_limit_h_min -8 _reflns_limit_h_max 8 _reflns_limit_k_min -16 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 20 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.62 _refine_diff_density_max 0.58 _refine_ls_number_reflns 3711 _refine_ls_number_restraints 0 _refine_ls_number_parameters 235 #_refine_ls_R_factor_ref 0.0330 _refine_ls_wR_factor_ref 0.0377 _refine_ls_goodness_of_fit_ref 1.1095 #_reflns_number_all 5877 _refine_ls_R_factor_all 0.0576 _refine_ls_wR_factor_all 0.0425 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.0\s(I) _reflns_number_gt 3711 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_gt 0.0377 _refine_ls_shift/su_max 0.000616 # 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: 3.99 -1.39 2.94 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # Some potentially useful phrases are: ; Hydrogen were initially refined with soft restraints on the bonds to regularise their geometry (bond lengths to accepted values, angles either set by symmetry or to accepted values, and U[iso] dependent upon the adjacent bonded atom), after which they were refined with riding constraints only. ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) J. Appl. Cryst. (27), 435-435 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 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 _atom_site_attached_hydrogens C1 C 0.9550(5) 0.3263(2) 0.74912(17) 0.0439 1.0000 Uani . . . . . . C2 C 0.8232(4) 0.2379(2) 0.67744(15) 0.0325 1.0000 Uani . . . . . . C3 C 0.7389(3) 0.25710(18) 0.59826(14) 0.0279 1.0000 Uani . . . . . . C4 C 0.6045(3) 0.16946(18) 0.52466(13) 0.0248 1.0000 Uani . . . . . . C5 C 0.9202(3) 0.12252(17) 0.44074(13) 0.0228 1.0000 Uani . . . . . . C6 C 0.9376(3) 0.00815(18) 0.46363(13) 0.0236 1.0000 Uani . . . . . . C7 C 0.6653(3) 0.18774(16) 0.26588(13) 0.0191 1.0000 Uani . . . . . . C8 C 0.6455(3) 0.30548(16) 0.27831(13) 0.0211 1.0000 Uani . . . . . . C9 C 0.7165(3) 0.36057(17) 0.21315(13) 0.0247 1.0000 Uani . . . . . . C10 C 0.8072(3) 0.30644(17) 0.13909(13) 0.0253 1.0000 Uani . . . . . . C11 C 0.8332(3) 0.19219(17) 0.13076(13) 0.0254 1.0000 Uani . . . . . . C12 C 0.7671(3) 0.13023(16) 0.19341(13) 0.0206 1.0000 Uani . . . . . . C13 C 0.8125(3) 0.00629(16) 0.17606(14) 0.0240 1.0000 Uani . . . . . . C14 C 1.0369(4) -0.0115(2) 0.14938(16) 0.0328 1.0000 Uani . . . . . . C15 C 0.6403(4) -0.06434(19) 0.10225(17) 0.0356 1.0000 Uani . . . . . . C16 C 0.8758(4) 0.37092(18) 0.06887(15) 0.0307 1.0000 Uani . . . . . . C17 C 1.0910(5) 0.3431(3) 0.0394(2) 0.0542 1.0000 Uani . . . . . . C18 C 0.7020(5) 0.3513(3) -0.01301(19) 0.0535 1.0000 Uani . . . . . . C19 C 0.5524(3) 0.37824(17) 0.35688(14) 0.0257 1.0000 Uani . . . . . . C20 C 0.3350(4) 0.4148(2) 0.32196(18) 0.0439 1.0000 Uani . . . . . . C21 C 0.7109(5) 0.4807(2) 0.40485(17) 0.0463 1.0000 Uani . . . . . . Br1 Br 1.25752(5) 0.29349(3) 0.75976(2) 0.0581 1.0000 Uani . . . . . . N1 N 0.7009(2) 0.16086(14) 0.43891(11) 0.0207 1.0000 Uani . . . . . . O1 O 0.3365(2) 0.15848(13) 0.35520(10) 0.0272 1.0000 Uani . . . . . . O2 O 0.5368(2) -0.00437(12) 0.31062(10) 0.0284 1.0000 Uani . . . . . . S1 S 0.54119(7) 0.11553(4) 0.34194(3) 0.0199 1.0000 Uani . . . . . . H21 H 0.7984 0.1604 0.6896 0.0392 1.0000 Uiso R . . . . . H31 H 0.7662 0.3347 0.5866 0.0337 1.0000 Uiso R . . . . . H41 H 0.6008 0.0947 0.5430 0.0308 1.0000 Uiso R . . . . . H42 H 0.4542 0.1919 0.5153 0.0308 1.0000 Uiso R . . . . . H51 H 1.0200 0.1791 0.4875 0.0290 1.0000 Uiso R . . . . . H52 H 0.9662 0.1194 0.3790 0.0290 1.0000 Uiso R . . . . . H61 H 0.8509 -0.0588 0.4221 0.0294 1.0000 Uiso R . . . . . H91 H 0.7010 0.4433 0.2204 0.0302 1.0000 Uiso R . . . . . H111 H 0.9021 0.1526 0.0781 0.0318 1.0000 Uiso R . . . . . H131 H 0.8028 -0.0209 0.2339 0.0293 1.0000 Uiso R . . . . . H141 H 1.0580 -0.0939 0.1388 0.0393 1.0000 Uiso R . . . . . H142 H 1.1483 0.0314 0.1997 0.0393 1.0000 Uiso R . . . . . H143 H 1.0515 0.0163 0.0921 0.0393 1.0000 Uiso R . . . . . H151 H 0.6712 -0.1454 0.0912 0.0408 1.0000 Uiso R . . . . . H152 H 0.6422 -0.0364 0.0443 0.0408 1.0000 Uiso R . . . . . H153 H 0.4950 -0.0573 0.1230 0.0408 1.0000 Uiso R . . . . . H161 H 0.8894 0.4533 0.0979 0.0374 1.0000 Uiso R . . . . . H171 H 1.1267 0.3880 -0.0066 0.0700 1.0000 Uiso R . . . . . H172 H 1.2051 0.3622 0.0937 0.0700 1.0000 Uiso R . . . . . H173 H 1.0840 0.2606 0.0114 0.0700 1.0000 Uiso R . . . . . H181 H 0.7485 0.3939 -0.0588 0.0671 1.0000 Uiso R . . . . . H182 H 0.5648 0.3783 0.0073 0.0671 1.0000 Uiso R . . . . . H183 H 0.6781 0.2687 -0.0415 0.0671 1.0000 Uiso R . . . . . H191 H 0.5272 0.3310 0.4025 0.0317 1.0000 Uiso R . . . . . H201 H 0.2753 0.4624 0.3739 0.0552 1.0000 Uiso R . . . . . H202 H 0.3551 0.4595 0.2742 0.0552 1.0000 Uiso R . . . . . H203 H 0.2323 0.3462 0.2949 0.0552 1.0000 Uiso R . . . . . H211 H 0.6458 0.5268 0.4559 0.0536 1.0000 Uiso R . . . . . H212 H 0.8482 0.4540 0.4300 0.0536 1.0000 Uiso R . . . . . H213 H 0.7421 0.5281 0.3600 0.0536 1.0000 Uiso R . . . . . H11 H 0.8998 0.3283 0.8090 0.0512 1.0000 Uiso R . . . . . H12 H 0.9440 0.4014 0.7321 0.0512 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 0.0503(15) 0.0476(15) 0.0285(12) 0.0000(10) 0.0023(10) -0.0020(12) C2 0.0375(12) 0.0357(11) 0.0246(10) 0.0060(9) 0.0078(8) 0.0003(9) C3 0.0292(10) 0.0280(10) 0.0271(10) 0.0045(8) 0.0072(8) 0.0052(8) C4 0.0224(9) 0.0343(11) 0.0201(9) 0.0092(8) 0.0073(7) 0.0025(8) C5 0.0158(8) 0.0318(10) 0.0247(9) 0.0128(8) 0.0043(7) 0.0057(7) C6 0.0191(8) 0.0313(10) 0.0232(9) 0.0102(8) 0.0044(7) 0.0064(7) C7 0.0163(8) 0.0229(9) 0.0199(8) 0.0089(7) 0.0027(6) 0.0013(6) C8 0.0226(9) 0.0219(9) 0.0204(9) 0.0071(7) 0.0040(7) 0.0047(7) C9 0.0325(10) 0.0207(9) 0.0222(9) 0.0062(8) 0.0060(8) 0.0029(8) C10 0.0332(10) 0.0248(9) 0.0198(9) 0.0082(8) 0.0065(7) -0.0001(8) C11 0.0327(10) 0.0255(9) 0.0207(9) 0.0069(8) 0.0105(8) 0.0044(8) C12 0.0208(9) 0.0200(8) 0.0207(9) 0.0033(7) 0.0035(7) 0.0025(7) C13 0.0284(10) 0.0224(9) 0.0225(9) 0.0059(7) 0.0050(7) 0.0065(7) C14 0.0278(11) 0.0364(12) 0.0339(12) 0.0042(9) 0.0025(9) 0.0126(9) C15 0.0308(11) 0.0250(10) 0.0467(14) 0.0010(10) -0.0005(10) 0.0018(8) C16 0.0470(13) 0.0227(9) 0.0239(10) 0.0063(8) 0.0123(9) -0.0019(9) C17 0.0467(15) 0.071(2) 0.0579(17) 0.0353(16) 0.0235(13) -0.0001(14) C18 0.0529(16) 0.074(2) 0.0408(15) 0.0358(14) 0.0031(12) -0.0079(14) C19 0.0313(10) 0.0260(9) 0.0219(9) 0.0065(8) 0.0070(8) 0.0083(8) C20 0.0482(14) 0.0540(16) 0.0354(13) 0.0109(11) 0.0115(11) 0.0326(13) C21 0.0661(18) 0.0390(13) 0.0289(12) -0.0047(10) 0.0157(12) -0.0084(12) Br1 0.05236(18) 0.03997(15) 0.0770(2) 0.02188(14) -0.02436(15) -0.00297(12) N1 0.0153(7) 0.0307(8) 0.0196(8) 0.0121(6) 0.0039(6) 0.0046(6) O1 0.0154(6) 0.0407(8) 0.0293(7) 0.0154(6) 0.0041(5) 0.0036(6) O2 0.0317(8) 0.0246(7) 0.0303(8) 0.0107(6) 0.0054(6) -0.0037(6) S1 0.0159(2) 0.0250(2) 0.0212(2) 0.01066(18) 0.00245(15) 0.00052(16) _refine_ls_extinction_method None 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 . 1.483(3) yes C1 . Br1 . 1.959(3) yes C1 . H11 . 1.000 no C1 . H12 . 1.000 no C2 . C3 . 1.319(3) yes C2 . H21 . 1.000 no C3 . C4 . 1.500(3) yes C3 . H31 . 1.000 no C4 . N1 . 1.477(2) yes C4 . H41 . 1.000 no C4 . H42 . 1.000 no C5 . C6 . 1.504(3) yes C5 . N1 . 1.479(3) yes C5 . H51 . 1.000 no C5 . H52 . 1.000 no C6 . C6 2_756 1.328(4) yes C6 . H61 . 1.000 no C7 . C8 . 1.418(3) yes C7 . C12 . 1.414(3) yes C7 . S1 . 1.7916(19) yes C8 . C9 . 1.392(3) yes C8 . C19 . 1.525(3) yes C9 . C10 . 1.378(3) yes C9 . H91 . 1.000 no C10 . C11 . 1.389(3) yes C10 . C16 . 1.521(3) yes C11 . C12 . 1.402(3) yes C11 . H111 . 1.000 no C12 . C13 . 1.525(3) yes C13 . C14 . 1.524(3) yes C13 . C15 . 1.530(3) yes C13 . H131 . 1.000 no C14 . H141 . 1.000 no C14 . H142 . 1.000 no C14 . H143 . 1.000 no C15 . H151 . 1.000 no C15 . H152 . 1.000 no C15 . H153 . 1.000 no C16 . C17 . 1.507(4) yes C16 . C18 . 1.515(4) yes C16 . H161 . 1.000 no C17 . H171 . 1.000 no C17 . H172 . 1.000 no C17 . H173 . 1.000 no C18 . H181 . 1.000 no C18 . H182 . 1.000 no C18 . H183 . 1.000 no C19 . C20 . 1.529(3) yes C19 . C21 . 1.534(3) yes C19 . H191 . 1.000 no C20 . H201 . 1.000 no C20 . H202 . 1.000 no C20 . H203 . 1.000 no C21 . H211 . 1.000 no C21 . H212 . 1.000 no C21 . H213 . 1.000 no N1 . S1 . 1.6419(17) yes O1 . S1 . 1.4368(17) yes O2 . S1 . 1.4323(16) 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 C2 . C1 . Br1 . 109.97(19) yes C2 . C1 . H11 . 109.4 no Br1 . C1 . H11 . 109.5 no C2 . C1 . H12 . 109.2 no Br1 . C1 . H12 . 109.3 no H11 . C1 . H12 . 109.5 no C1 . C2 . C3 . 122.8(2) yes C1 . C2 . H21 . 118.4 no C3 . C2 . H21 . 118.8 no C2 . C3 . C4 . 123.9(2) yes C2 . C3 . H31 . 118.1 no C4 . C3 . H31 . 118.0 no C3 . C4 . N1 . 108.99(16) yes C3 . C4 . H41 . 109.6 no N1 . C4 . H41 . 109.6 no C3 . C4 . H42 . 109.6 no N1 . C4 . H42 . 109.6 no H41 . C4 . H42 . 109.5 no C6 . C5 . N1 . 114.50(15) yes C6 . C5 . H51 . 108.2 no N1 . C5 . H51 . 108.2 no C6 . C5 . H52 . 108.2 no N1 . C5 . H52 . 108.2 no H51 . C5 . H52 . 109.5 no C5 . C6 . C6 2_756 123.1(2) yes C5 . C6 . H61 . 118.4 no C6 2_756 C6 . H61 . 118.4 no C8 . C7 . C12 . 121.03(17) yes C8 . C7 . S1 . 116.62(14) yes C12 . C7 . S1 . 122.24(14) yes C7 . C8 . C9 . 117.58(18) yes C7 . C8 . C19 . 125.98(17) yes C9 . C8 . C19 . 116.43(18) yes C8 . C9 . C10 . 123.08(19) yes C8 . C9 . H91 . 118.4 no C10 . C9 . H91 . 118.5 no C9 . C10 . C11 . 118.10(18) yes C9 . C10 . C16 . 120.45(18) yes C11 . C10 . C16 . 121.45(19) yes C10 . C11 . C12 . 122.59(19) yes C10 . C11 . H111 . 118.7 no C12 . C11 . H111 . 118.7 no C7 . C12 . C11 . 117.45(17) yes C7 . C12 . C13 . 126.38(17) yes C11 . C12 . C13 . 116.18(18) yes C12 . C13 . C14 . 112.76(17) yes C12 . C13 . C15 . 109.96(16) yes C14 . C13 . C15 . 110.19(18) yes C12 . C13 . H131 . 108.0 no C14 . C13 . H131 . 107.9 no C15 . C13 . H131 . 107.9 no C13 . C14 . H141 . 109.5 no C13 . C14 . H142 . 109.5 no H141 . C14 . H142 . 109.5 no C13 . C14 . H143 . 109.5 no H141 . C14 . H143 . 109.5 no H142 . C14 . H143 . 109.5 no C13 . C15 . H151 . 109.5 no C13 . C15 . H152 . 109.5 no H151 . C15 . H152 . 109.5 no C13 . C15 . H153 . 109.4 no H151 . C15 . H153 . 109.5 no H152 . C15 . H153 . 109.5 no C10 . C16 . C17 . 113.4(2) yes C10 . C16 . C18 . 110.03(19) yes C17 . C16 . C18 . 110.8(2) yes C10 . C16 . H161 . 107.4 no C17 . C16 . H161 . 107.4 no C18 . C16 . H161 . 107.5 no C16 . C17 . H171 . 109.5 no C16 . C17 . H172 . 109.4 no H171 . C17 . H172 . 109.5 no C16 . C17 . H173 . 109.5 no H171 . C17 . H173 . 109.5 no H172 . C17 . H173 . 109.5 no C16 . C18 . H181 . 109.5 no C16 . C18 . H182 . 109.4 no H181 . C18 . H182 . 109.5 no C16 . C18 . H183 . 109.5 no H181 . C18 . H183 . 109.5 no H182 . C18 . H183 . 109.5 no C8 . C19 . C20 . 110.12(18) yes C8 . C19 . C21 . 111.20(19) yes C20 . C19 . C21 . 111.3(2) yes C8 . C19 . H191 . 108.0 no C20 . C19 . H191 . 108.1 no C21 . C19 . H191 . 108.1 no C19 . C20 . H201 . 109.5 no C19 . C20 . H202 . 109.5 no H201 . C20 . H202 . 109.5 no C19 . C20 . H203 . 109.4 no H201 . C20 . H203 . 109.5 no H202 . C20 . H203 . 109.5 no C19 . C21 . H211 . 109.5 no C19 . C21 . H212 . 109.4 no H211 . C21 . H212 . 109.5 no C19 . C21 . H213 . 109.5 no H211 . C21 . H213 . 109.5 no H212 . C21 . H213 . 109.5 no C5 . N1 . C4 . 115.91(14) yes C5 . N1 . S1 . 115.29(13) yes C4 . N1 . S1 . 117.86(13) yes C7 . S1 . N1 . 102.47(9) yes C7 . S1 . O1 . 108.66(10) yes N1 . S1 . O1 . 106.61(10) yes C7 . S1 . O2 . 110.35(10) yes N1 . S1 . O2 . 111.74(9) yes O1 . S1 . O2 . 116.07(10) yes