# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2012 data_global _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 #TrackingRef '- FHD021_publish.cif' _audit_creation_date 11-07-21 _audit_creation_method CRYSTALS_ver_14.11 _oxford_structure_analysis_title 'fhd021 in P 1 21/c 1' _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_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Acta Crystallographica E. ; _publ_contact_author_name 'Olivier Maury' _publ_contact_author_address ; Chemical Crystallography Laboratory, Department of Chemistry, University of Nowhere, Nowhere, NO1 4T, UK. ; _publ_contact_author_phone '+44 1865 000000' _publ_contact_author_fax '+44 1865 000000' _publ_contact_author_email olivier.maury@ens-lyon.fr _publ_requested_category EO # choose from: FI FM FO CI CM CO AD _publ_requested_coeditor_name 'Prof William Clegg' _publ_section_title # Title of paper - generally just the systematic or trivial name ; ? ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address _publ_author_footnote # Author 1 # Author 2 'Olivier Maury' ; ? # Address for author 1 ; ; ? # Footnote for author 1 ; 'Quentin Bellier' ; ? # Address 2 ; ; ? # Footnote 2 ; 'Chantal Andraud' '' '' 'Fabrice Dalier' '' '' 'Erwann Jeanneau' '' '' _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_related_literature # Not in version 2.3.1 ############################################################### # Essential references (e.g. to the origin of the material studied, related # structural studies, and to information supporting the reported structure) # should be cited in this section, with appropriate very brief explanatory # text, for example `The synthesis of the complex is described by Jones # (2001). The anhydrous complex has essentially the same coordination # geometry (Smith, 2003).' In addition, all references included in the # supplementary materials, but not elsewhere in the published article, # should be given here. The simple text `For related literature, see:...' # may be used, but further details should be provided in the Comment # section, which forms part of the supplementary material. ############################################################### ; ? ; _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 Fig. ; ? ; _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 ; ? ; # 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)" # data_1 _database_code_depnum_ccdc_archive 'CCDC 836074' #TrackingRef '- FHD021_publish.cif' _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107. ; _refine_special_details ; ? ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 14.6060(10) _cell_length_b 14.2120(10) _cell_length_c 25.060(2) _cell_angle_alpha 90 _cell_angle_beta 106.091(7) _cell_angle_gamma 90 _cell_volume 4998.2(7) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x,-y+1/2,z+1/2 -x,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 0.0181 0.0091 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' B 0.0090 0.0039 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403 -0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Br -0.6763 1.2805 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' F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0311 0.0180 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' S 0.3331 0.5567 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' _cell_formula_units_Z 8 # Given Formula = C2.80 B25.20 Br1.60 F0.80 N2.40 S1.60 # Dc = 1.77 Fooo = 2640.00 Mu = 57.91 M = 1335.09 # Found Formula = C22.40 H12.80 B0.80 Br1.60 F1.60 N2.40 S1.60 # Dc = 1.77 FOOO = 2640.00 Mu = 60.22 M = 1334.40 _chemical_formula_sum 'C28 H16 B Br2 F2 N3 S2' _chemical_formula_moiety 'C28 H16 B Br2 F2 N3 S2' _chemical_compound_source ? _chemical_formula_weight 667.19 _cell_measurement_reflns_used 13101 _cell_measurement_theta_min 3.6084 _cell_measurement_theta_max 67.3736 _cell_measurement_temperature 110 _exptl_crystal_description plate _exptl_crystal_colour 'dark red' _exptl_crystal_size_min 0.080 _exptl_crystal_size_mid 0.171 _exptl_crystal_size_max 0.355 _exptl_crystal_density_diffrn 1.773 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 2640 _exptl_absorpt_coefficient_mu 6.022 # Sheldrick geometric approximatio 0.36 0.62 _exptl_absorpt_correction_T_min 0.159 _exptl_absorpt_correction_T_max 0.457 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_detector_area_resol_mean 10.4685 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _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 110 _diffrn_reflns_number 54285 _reflns_number_total 8863 _diffrn_reflns_av_R_equivalents 0.073 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 8863 # Theoretical number of reflections is about 18012 _diffrn_reflns_theta_min 3.611 _diffrn_reflns_theta_max 67.483 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 66.906 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _reflns_limit_h_min -17 _reflns_limit_h_max 16 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 29 _oxford_diffrn_Wilson_B_factor 1.77 _oxford_diffrn_Wilson_scale 0.26 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.71 _refine_diff_density_max 0.66 # 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>-10.0\s(I) _refine_ls_number_reflns 8863 _refine_ls_number_restraints 0 _refine_ls_number_parameters 686 _oxford_refine_ls_R_factor_ref 0.0418 _refine_ls_wR_factor_ref 0.1129 _refine_ls_goodness_of_fit_ref 1.0071 _refine_ls_shift/su_max 0.0020631 _refine_ls_shift/su_mean 0.0000674 # The values computed from all data _oxford_reflns_number_all 8863 _refine_ls_R_factor_all 0.0418 _refine_ls_wR_factor_all 0.1129 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 8407 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_gt 0.1118 # 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 none # 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: 0.142E+04 0.241E+04 0.150E+04 626. 139. ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Grazia, A., Moliterni, G., Polidori, G. & Spagna, R. (1999). J. App. Cryst. 32, 115-119. 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. Oxford Diffraction, (2002). CrysAlis RED. Oxford Diffraction, (2006). Gemini 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 Br1 Br 0.140025(17) 0.650743(17) 0.409122(10) 0.0235 1.0000 Uani . . . . . . C2 C 0.25543(16) 0.64476(15) 0.46448(10) 0.0184 1.0000 Uani . . . . . . S3 S 0.35988(4) 0.63562(4) 0.44641(2) 0.0172 1.0000 Uani . . . . . . C4 C 0.42483(16) 0.62734(16) 0.51577(9) 0.0157 1.0000 Uani . . . . . . C5 C 0.52619(16) 0.61580(15) 0.52755(9) 0.0154 1.0000 Uani . . . . . . N6 N 0.58968(13) 0.59730(12) 0.57829(8) 0.0144 1.0000 Uani . . . . . . C7 C 0.67980(16) 0.59351(14) 0.57046(9) 0.0151 1.0000 Uani . . . . . . N8 N 0.75781(13) 0.57212(12) 0.60991(7) 0.0151 1.0000 Uani . . . . . . C9 C 0.75279(15) 0.55056(15) 0.66027(9) 0.0148 1.0000 Uani . . . . . . N10 N 0.66753(13) 0.54678(13) 0.67528(7) 0.0140 1.0000 Uani . . . . . . B11 B 0.57018(17) 0.57579(18) 0.63464(10) 0.0160 1.0000 Uani . . . . . . F12 F 0.53531(9) 0.65462(9) 0.65509(5) 0.0191 1.0000 Uani . . . . . . F13 F 0.50580(9) 0.50206(9) 0.62870(5) 0.0196 1.0000 Uani . . . . . . C14 C 0.68937(17) 0.52013(15) 0.72930(9) 0.0156 1.0000 Uani . . . . . . C15 C 0.62487(17) 0.50670(15) 0.76297(10) 0.0176 1.0000 Uani . . . . . . S16 S 0.50261(4) 0.51978(5) 0.74179(2) 0.0233 1.0000 Uani . . . . . . C17 C 0.49456(17) 0.49313(17) 0.80680(10) 0.0207 1.0000 Uani . . . . . . Br18 Br 0.375850(19) 0.49708(2) 0.820780(11) 0.0300 1.0000 Uani . . . . . . C19 C 0.58008(18) 0.47427(18) 0.84366(10) 0.0229 1.0000 Uani . . . . . . C20 C 0.65459(17) 0.48213(18) 0.81882(10) 0.0229 1.0000 Uani . . . . . . H201 H 0.7165 0.4717 0.8374 0.0274 1.0000 Uiso R . . . . . H191 H 0.5894 0.4587 0.8806 0.0279 1.0000 Uiso R . . . . . C21 C 0.78861(16) 0.50580(15) 0.74944(9) 0.0161 1.0000 Uani . . . . . . C22 C 0.82996(16) 0.52495(15) 0.70756(9) 0.0157 1.0000 Uani . . . . . . C23 C 0.93221(16) 0.52248(15) 0.71144(9) 0.0151 1.0000 Uani . . . . . . C24 C 0.99725(17) 0.49125(16) 0.76022(10) 0.0186 1.0000 Uani . . . . . . C25 C 1.09389(18) 0.49017(17) 0.76588(10) 0.0215 1.0000 Uani . . . . . . C26 C 1.12843(16) 0.52093(17) 0.72210(10) 0.0206 1.0000 Uani . . . . . . C27 C 1.06451(17) 0.55121(17) 0.67309(10) 0.0209 1.0000 Uani . . . . . . C28 C 0.96772(16) 0.55158(16) 0.66758(9) 0.0180 1.0000 Uani . . . . . . H281 H 0.9265 0.5722 0.6351 0.0226 1.0000 Uiso R . . . . . H271 H 1.0866 0.5728 0.6440 0.0254 1.0000 Uiso R . . . . . H261 H 1.1926 0.5210 0.7269 0.0252 1.0000 Uiso R . . . . . H251 H 1.1356 0.4696 0.7988 0.0266 1.0000 Uiso R . . . . . H241 H 0.9749 0.4718 0.7901 0.0227 1.0000 Uiso R . . . . . H211 H 0.8209 0.4890 0.7853 0.0184 1.0000 Uiso R . . . . . C29 C 0.67215(16) 0.60888(15) 0.51267(10) 0.0157 1.0000 Uani . . . . . . C30 C 0.57680(16) 0.62207(16) 0.48704(9) 0.0168 1.0000 Uani . . . . . . H301 H 0.5491 0.6341 0.4501 0.0198 1.0000 Uiso R . . . . . C31 C 0.74953(17) 0.60529(15) 0.48574(10) 0.0175 1.0000 Uani . . . . . . C32 C 0.84376(17) 0.62157(16) 0.51525(10) 0.0186 1.0000 Uani . . . . . . C33 C 0.91617(18) 0.61381(18) 0.48943(11) 0.0255 1.0000 Uani . . . . . . C34 C 0.89362(19) 0.58874(19) 0.43356(12) 0.0296 1.0000 Uani . . . . . . C35 C 0.79983(19) 0.57428(19) 0.40356(10) 0.0277 1.0000 Uani . . . . . . C36 C 0.72752(17) 0.58229(17) 0.42952(10) 0.0214 1.0000 Uani . . . . . . H361 H 0.6641 0.5734 0.4079 0.0271 1.0000 Uiso R . . . . . H351 H 0.7830 0.5588 0.3663 0.0336 1.0000 Uiso R . . . . . H341 H 0.9432 0.5821 0.4166 0.0358 1.0000 Uiso R . . . . . H331 H 0.9790 0.6259 0.5085 0.0315 1.0000 Uiso R . . . . . H321 H 0.8595 0.6374 0.5531 0.0229 1.0000 Uiso R . . . . . C37 C 0.36524(17) 0.63405(17) 0.54972(10) 0.0211 1.0000 Uani . . . . . . C38 C 0.26866(17) 0.64309(17) 0.52038(10) 0.0217 1.0000 Uani . . . . . . H381 H 0.2211 0.6480 0.5378 0.0262 1.0000 Uiso R . . . . . H371 H 0.3872 0.6329 0.5884 0.0246 1.0000 Uiso R . . . . . Br39 Br 0.272447(19) 0.898983(18) 0.422373(11) 0.0260 1.0000 Uani . . . . . . C40 C 0.15675(18) 0.90190(16) 0.43969(10) 0.0214 1.0000 Uani . . . . . . S41 S 0.14781(4) 0.86200(4) 0.50238(2) 0.0204 1.0000 Uani . . . . . . C42 C 0.02618(17) 0.88508(16) 0.48338(9) 0.0180 1.0000 Uani . . . . . . C43 C -0.03961(17) 0.86710(16) 0.51554(9) 0.0173 1.0000 Uani . . . . . . N44 N -0.01941(13) 0.83735(13) 0.56937(8) 0.0154 1.0000 Uani . . . . . . C45 C -0.10577(16) 0.82988(15) 0.58296(9) 0.0159 1.0000 Uani . . . . . . N46 N -0.11224(13) 0.80491(13) 0.63234(7) 0.0146 1.0000 Uani . . . . . . C47 C -0.03444(16) 0.78467(15) 0.67263(10) 0.0162 1.0000 Uani . . . . . . N48 N 0.05682(14) 0.78676(13) 0.66610(8) 0.0153 1.0000 Uani . . . . . . B49 B 0.07745(18) 0.81264(18) 0.61077(10) 0.0168 1.0000 Uani . . . . . . F50 F 0.11761(10) 0.73757(9) 0.59003(5) 0.0206 1.0000 Uani . . . . . . F51 F 0.13812(9) 0.89063(9) 0.61828(5) 0.0208 1.0000 Uani . . . . . . C52 C 0.11960(16) 0.76596(15) 0.71655(9) 0.0163 1.0000 Uani . . . . . . C53 C 0.06799(17) 0.75069(16) 0.75539(9) 0.0179 1.0000 Uani . . . . . . C54 C -0.02812(17) 0.76010(15) 0.72928(9) 0.0166 1.0000 Uani . . . . . . C55 C -0.10526(17) 0.75086(15) 0.75576(10) 0.0178 1.0000 Uani . . . . . . C56 C -0.20130(19) 0.75741(18) 0.72649(10) 0.0243 1.0000 Uani . . . . . . C57 C -0.27224(18) 0.74967(18) 0.75316(12) 0.0269 1.0000 Uani . . . . . . C58 C -0.24816(18) 0.73413(18) 0.80987(11) 0.0255 1.0000 Uani . . . . . . C59 C -0.1533(2) 0.7266(2) 0.83973(11) 0.0294 1.0000 Uani . . . . . . C60 C -0.08272(18) 0.73455(19) 0.81317(10) 0.0245 1.0000 Uani . . . . . . H601 H -0.0198 0.7303 0.8334 0.0294 1.0000 Uiso R . . . . . H591 H -0.1357 0.7187 0.8786 0.0354 1.0000 Uiso R . . . . . H581 H -0.2949 0.7288 0.8285 0.0314 1.0000 Uiso R . . . . . H571 H -0.3354 0.7541 0.7330 0.0325 1.0000 Uiso R . . . . . H561 H -0.2175 0.7671 0.6886 0.0294 1.0000 Uiso R . . . . . H531 H 0.0945 0.7359 0.7919 0.0210 1.0000 Uiso R . . . . . C61 C 0.22212(16) 0.76178(16) 0.72886(9) 0.0178 1.0000 Uani . . . . . . S62 S 0.28683(4) 0.76853(4) 0.79814(2) 0.0212 1.0000 Uani . . . . . . C63 C 0.39111(17) 0.75565(16) 0.78096(10) 0.0218 1.0000 Uani . . . . . . Br64 Br 0.506306(19) 0.75430(2) 0.837158(12) 0.0338 1.0000 Uani . . . . . . C65 C 0.37872(18) 0.74628(18) 0.72552(11) 0.0244 1.0000 Uani . . . . . . C66 C 0.28144(18) 0.75057(18) 0.69562(11) 0.0247 1.0000 Uani . . . . . . H661 H 0.2608 0.7459 0.6572 0.0318 1.0000 Uiso R . . . . . H651 H 0.4268 0.7390 0.7089 0.0280 1.0000 Uiso R . . . . . C67 C -0.18210(17) 0.85560(15) 0.53463(9) 0.0176 1.0000 Uani . . . . . . C68 C -0.13934(17) 0.87862(16) 0.49419(9) 0.0184 1.0000 Uani . . . . . . H681 H -0.1712 0.8984 0.4585 0.0211 1.0000 Uiso R . . . . . C69 C -0.28516(17) 0.85667(15) 0.52866(10) 0.0178 1.0000 Uani . . . . . . C70 C -0.32296(17) 0.83050(18) 0.57160(10) 0.0231 1.0000 Uani . . . . . . C71 C -0.42026(18) 0.83303(18) 0.56509(11) 0.0253 1.0000 Uani . . . . . . C72 C -0.48130(19) 0.86219(19) 0.51574(12) 0.0277 1.0000 Uani . . . . . . C73 C -0.4452(2) 0.8875(2) 0.47198(12) 0.0362 1.0000 Uani . . . . . . C74 C -0.3480(2) 0.8851(2) 0.47869(12) 0.0324 1.0000 Uani . . . . . . H741 H -0.3234 0.9008 0.4487 0.0393 1.0000 Uiso R . . . . . H731 H -0.4869 0.9077 0.4384 0.0432 1.0000 Uiso R . . . . . H721 H -0.5467 0.8648 0.5124 0.0320 1.0000 Uiso R . . . . . H711 H -0.4428 0.8126 0.5944 0.0308 1.0000 Uiso R . . . . . H701 H -0.2819 0.8110 0.6057 0.0290 1.0000 Uiso R . . . . . C75 C -0.00121(18) 0.92326(17) 0.43054(10) 0.0227 1.0000 Uani . . . . . . C76 C 0.07257(18) 0.93267(18) 0.40541(10) 0.0234 1.0000 Uani . . . . . . H761 H 0.0663 0.9574 0.3700 0.0284 1.0000 Uiso R . . . . . H751 H -0.0623 0.9432 0.4131 0.0264 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 Br1 0.01175(15) 0.02946(17) 0.02527(16) -0.00170(9) -0.00167(11) 0.00187(9) C2 0.0099(11) 0.0197(11) 0.0248(12) 0.0009(9) 0.0034(9) 0.0020(8) S3 0.0112(3) 0.0228(3) 0.0161(3) -0.0003(2) 0.0014(2) 0.0019(2) C4 0.0115(11) 0.0189(10) 0.0149(10) 0.0005(8) 0.0006(8) 0.0019(8) C5 0.0125(11) 0.0162(10) 0.0157(10) 0.0006(8) 0.0011(9) 0.0020(8) N6 0.0100(9) 0.0173(9) 0.0156(9) 0.0005(7) 0.0032(7) 0.0018(7) C7 0.0120(11) 0.0149(10) 0.0179(11) -0.0004(8) 0.0033(8) 0.0013(8) N8 0.0133(9) 0.0163(9) 0.0155(9) -0.0014(7) 0.0036(7) -0.0002(7) C9 0.0085(10) 0.0186(10) 0.0175(11) -0.0007(8) 0.0038(8) 0.0009(8) N10 0.0086(9) 0.0180(9) 0.0151(9) -0.0003(7) 0.0027(7) 0.0014(7) B11 0.0095(11) 0.0213(12) 0.0174(12) -0.0006(10) 0.0038(9) 0.0020(9) F12 0.0155(7) 0.0247(7) 0.0172(6) -0.0016(5) 0.0048(5) 0.0053(5) F13 0.0125(7) 0.0260(7) 0.0191(7) 0.0012(5) 0.0022(5) -0.0026(5) C14 0.0160(11) 0.0151(10) 0.0165(11) -0.0003(8) 0.0058(9) 0.0018(8) C15 0.0143(11) 0.0186(11) 0.0208(12) 0.0014(8) 0.0065(9) 0.0020(8) S16 0.0121(3) 0.0416(3) 0.0164(3) 0.0068(2) 0.0042(2) 0.0043(2) C17 0.0169(12) 0.0283(12) 0.0184(11) 0.0020(9) 0.0073(9) 0.0008(9) Br18 0.01548(16) 0.0509(2) 0.02604(17) 0.00710(11) 0.00985(12) 0.00293(11) C19 0.0201(12) 0.0326(13) 0.0162(11) 0.0027(9) 0.0054(9) 0.0071(10) C20 0.0124(11) 0.0348(13) 0.0207(12) 0.0043(10) 0.0033(9) 0.0043(9) C21 0.0129(11) 0.0194(11) 0.0144(11) 0.0007(8) 0.0011(9) 0.0002(8) C22 0.0138(11) 0.0156(10) 0.0172(11) -0.0021(8) 0.0031(9) 0.0005(8) C23 0.0127(11) 0.0151(10) 0.0158(10) -0.0018(8) 0.0014(8) 0.0005(8) C24 0.0160(12) 0.0208(11) 0.0178(11) 0.0009(8) 0.0028(9) -0.0002(9) C25 0.0157(12) 0.0256(12) 0.0202(12) 0.0004(9) 0.0000(9) 0.0036(9) C26 0.0107(11) 0.0252(11) 0.0260(13) -0.0056(9) 0.0053(9) -0.0008(9) C27 0.0189(12) 0.0247(12) 0.0203(11) -0.0016(9) 0.0072(9) -0.0004(9) C28 0.0156(11) 0.0229(11) 0.0148(10) 0.0014(8) 0.0029(8) 0.0033(9) C29 0.0124(11) 0.0163(10) 0.0192(11) -0.0005(8) 0.0057(9) 0.0011(8) C30 0.0144(11) 0.0232(11) 0.0122(10) 0.0000(8) 0.0026(8) 0.0033(9) C31 0.0162(11) 0.0189(11) 0.0197(11) 0.0029(8) 0.0086(9) 0.0019(8) C32 0.0136(11) 0.0228(11) 0.0187(11) 0.0008(9) 0.0032(9) -0.0018(9) C33 0.0158(11) 0.0303(13) 0.0310(13) -0.0025(10) 0.0078(10) -0.0010(10) C34 0.0222(13) 0.0389(14) 0.0321(14) -0.0038(11) 0.0150(11) -0.0015(11) C35 0.0274(14) 0.0405(14) 0.0183(12) -0.0063(10) 0.0115(10) -0.0016(11) C36 0.0156(11) 0.0271(12) 0.0218(12) -0.0005(9) 0.0055(9) 0.0013(9) C37 0.0168(12) 0.0265(12) 0.0194(11) 0.0008(9) 0.0041(9) 0.0051(9) C38 0.0136(12) 0.0280(12) 0.0248(13) 0.0029(9) 0.0076(10) 0.0032(9) Br39 0.02187(17) 0.03161(17) 0.02764(17) 0.00321(10) 0.01211(12) 0.00201(10) C40 0.0236(13) 0.0218(11) 0.0201(12) 0.0000(9) 0.0081(10) 0.0008(9) S41 0.0173(3) 0.0264(3) 0.0180(3) 0.0052(2) 0.0057(2) 0.0048(2) C42 0.0178(11) 0.0188(11) 0.0168(11) -0.0015(8) 0.0038(9) 0.0035(9) C43 0.0187(12) 0.0152(10) 0.0164(11) -0.0017(8) 0.0022(9) 0.0002(8) N44 0.0110(9) 0.0194(9) 0.0150(9) 0.0004(7) 0.0021(7) 0.0000(7) C45 0.0143(11) 0.0150(10) 0.0179(11) -0.0017(8) 0.0036(9) -0.0003(8) N46 0.0133(9) 0.0169(9) 0.0126(9) -0.0012(6) 0.0017(7) -0.0005(7) C47 0.0126(11) 0.0132(10) 0.0222(11) -0.0016(8) 0.0037(9) -0.0004(8) N48 0.0139(9) 0.0170(9) 0.0147(9) -0.0007(7) 0.0036(7) 0.0011(7) B49 0.0137(12) 0.0195(12) 0.0171(12) 0.0019(9) 0.0040(10) -0.0008(9) F50 0.0192(7) 0.0265(7) 0.0165(6) 0.0011(5) 0.0058(5) 0.0066(5) F51 0.0151(7) 0.0256(7) 0.0194(6) 0.0029(5) 0.0008(5) -0.0051(5) C52 0.0145(11) 0.0172(10) 0.0159(11) -0.0011(8) 0.0022(9) 0.0010(8) C53 0.0159(12) 0.0220(11) 0.0143(11) 0.0017(8) 0.0018(9) -0.0002(9) C54 0.0175(12) 0.0163(10) 0.0155(11) -0.0013(8) 0.0038(9) -0.0001(8) C55 0.0169(12) 0.0178(11) 0.0183(11) -0.0006(8) 0.0044(9) -0.0017(8) C56 0.0180(13) 0.0342(13) 0.0198(12) 0.0033(10) 0.0036(10) 0.0017(10) C57 0.0111(12) 0.0331(14) 0.0362(14) 0.0036(11) 0.0060(10) 0.0014(9) C58 0.0208(13) 0.0332(13) 0.0274(13) -0.0009(10) 0.0150(10) -0.0002(10) C59 0.0256(13) 0.0405(14) 0.0244(13) 0.0028(11) 0.0106(10) -0.0007(11) C60 0.0147(11) 0.0367(13) 0.0202(12) 0.0015(10) 0.0017(9) 0.0015(10) C61 0.0110(11) 0.0238(11) 0.0165(11) 0.0017(8) 0.0003(9) 0.0014(8) S62 0.0130(3) 0.0322(3) 0.0169(3) -0.0008(2) 0.0015(2) 0.0040(2) C63 0.0114(11) 0.0251(12) 0.0260(13) 0.0015(9) 0.0005(10) 0.0021(9) Br64 0.01411(17) 0.0488(2) 0.03264(18) -0.00743(12) -0.00353(12) 0.00641(11) C65 0.0148(12) 0.0350(14) 0.0258(13) 0.0049(10) 0.0097(10) 0.0034(9) C66 0.0173(12) 0.0338(14) 0.0225(12) 0.0039(10) 0.0046(10) 0.0055(10) C67 0.0179(12) 0.0148(10) 0.0179(11) -0.0017(8) 0.0013(9) 0.0018(8) C68 0.0169(11) 0.0222(11) 0.0142(11) 0.0032(9) 0.0013(9) 0.0026(9) C69 0.0136(11) 0.0158(10) 0.0227(12) -0.0010(8) 0.0027(9) 0.0014(8) C70 0.0165(12) 0.0306(13) 0.0188(11) 0.0024(10) -0.0009(9) 0.0033(10) C71 0.0205(12) 0.0301(13) 0.0250(13) 0.0021(10) 0.0061(10) -0.0008(10) C72 0.0134(12) 0.0316(13) 0.0362(15) -0.0013(11) 0.0036(10) 0.0012(10) C73 0.0176(13) 0.0589(19) 0.0262(14) 0.0115(13) -0.0038(11) 0.0054(12) C74 0.0207(13) 0.0486(16) 0.0250(13) 0.0100(12) 0.0018(11) 0.0015(12) C75 0.0196(12) 0.0255(12) 0.0229(12) 0.0030(10) 0.0059(9) 0.0021(9) C76 0.0230(12) 0.0267(12) 0.0200(11) 0.0052(9) 0.0050(9) 0.0030(10) _refine_ls_extinction_coef 48(3) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 1.004(3) 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 . 1.865(2) yes C2 . S3 . 1.712(2) yes C2 . C38 . 1.360(3) yes S3 . C4 . 1.738(2) yes C4 . C5 . 1.436(3) yes C4 . C37 . 1.379(3) yes C5 . N6 . 1.376(3) yes C5 . C30 . 1.414(3) yes N6 . C7 . 1.385(3) yes N6 . B11 . 1.547(3) yes C7 . N8 . 1.320(3) yes C7 . C29 . 1.438(3) yes N8 . C9 . 1.320(3) yes C9 . N10 . 1.398(3) yes C9 . C22 . 1.438(3) yes N10 . B11 . 1.558(3) yes N10 . C14 . 1.356(3) yes B11 . F12 . 1.386(3) yes B11 . F13 . 1.388(3) yes C14 . C15 . 1.441(3) yes C14 . C21 . 1.411(3) yes C15 . S16 . 1.726(2) yes C15 . C20 . 1.390(3) yes S16 . C17 . 1.708(2) yes C17 . Br18 . 1.863(2) yes C17 . C19 . 1.359(3) yes C19 . C20 . 1.400(3) yes C19 . H191 . 0.925 no C20 . H201 . 0.907 no C21 . C22 . 1.375(3) yes C21 . H211 . 0.923 no C22 . C23 . 1.470(3) yes C23 . C24 . 1.396(3) yes C23 . C28 . 1.402(3) yes C24 . C25 . 1.379(4) yes C24 . H241 . 0.939 no C25 . C26 . 1.399(3) yes C25 . H251 . 0.926 no C26 . C27 . 1.389(3) yes C26 . H261 . 0.911 no C27 . C28 . 1.382(3) yes C27 . H271 . 0.927 no C28 . H281 . 0.916 no C29 . C30 . 1.375(3) yes C29 . C31 . 1.469(3) yes C30 . H301 . 0.919 no C31 . C32 . 1.389(3) yes C31 . C36 . 1.394(3) yes C32 . C33 . 1.389(4) yes C32 . H321 . 0.940 no C33 . C34 . 1.393(4) yes C33 . H331 . 0.926 no C34 . C35 . 1.383(4) yes C34 . H341 . 0.940 no C35 . C36 . 1.390(3) yes C35 . H351 . 0.923 no C36 . H361 . 0.943 no C37 . C38 . 1.404(3) yes C37 . H371 . 0.934 no C38 . H381 . 0.919 no Br39 . C40 . 1.858(3) yes C40 . S41 . 1.709(2) yes C40 . C76 . 1.362(4) yes S41 . C42 . 1.738(2) yes C42 . C43 . 1.438(3) yes C42 . C75 . 1.384(3) yes C43 . N44 . 1.366(3) yes C43 . C68 . 1.415(3) yes N44 . C45 . 1.399(3) yes N44 . B49 . 1.545(3) yes C45 . N46 . 1.316(3) yes C45 . C67 . 1.448(3) yes N46 . C47 . 1.326(3) yes C47 . N48 . 1.388(3) yes C47 . C54 . 1.440(3) yes N48 . B49 . 1.543(3) yes N48 . C52 . 1.373(3) yes B49 . F50 . 1.386(3) yes B49 . F51 . 1.399(3) yes C52 . C53 . 1.403(3) yes C52 . C61 . 1.444(3) yes C53 . C54 . 1.381(3) yes C53 . H531 . 0.914 no C54 . C55 . 1.463(3) yes C55 . C56 . 1.394(4) yes C55 . C60 . 1.403(3) yes C56 . C57 . 1.384(4) yes C56 . H561 . 0.922 no C57 . C58 . 1.384(4) yes C57 . H571 . 0.923 no C58 . C59 . 1.385(4) yes C58 . H581 . 0.931 no C59 . C60 . 1.378(4) yes C59 . H591 . 0.943 no C60 . H601 . 0.920 no C61 . S62 . 1.734(2) yes C61 . C66 . 1.367(3) yes S62 . C63 . 1.704(2) yes C63 . Br64 . 1.871(2) yes C63 . C65 . 1.357(4) yes C65 . C66 . 1.412(4) yes C65 . H651 . 0.915 no C66 . H661 . 0.927 no C67 . C68 . 1.369(3) yes C67 . C69 . 1.471(3) yes C68 . H681 . 0.930 no C69 . C70 . 1.389(3) yes C69 . C74 . 1.392(3) yes C70 . C71 . 1.385(3) yes C70 . H701 . 0.939 no C71 . C72 . 1.373(4) yes C71 . H711 . 0.930 no C72 . C73 . 1.390(4) yes C72 . H721 . 0.937 no C73 . C74 . 1.383(4) yes C73 . H731 . 0.937 no C74 . H741 . 0.945 no C75 . C76 . 1.397(3) yes C75 . H751 . 0.922 no C76 . H761 . 0.935 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 Br1 . C2 . S3 . 119.65(14) yes Br1 . C2 . C38 . 127.45(18) yes S3 . C2 . C38 . 112.85(18) yes C2 . S3 . C4 . 91.15(11) yes S3 . C4 . C5 . 117.32(17) yes S3 . C4 . C37 . 110.45(17) yes C5 . C4 . C37 . 132.2(2) yes C4 . C5 . N6 . 127.2(2) yes C4 . C5 . C30 . 124.0(2) yes N6 . C5 . C30 . 108.85(19) yes C5 . N6 . C7 . 107.47(18) yes C5 . N6 . B11 . 129.37(18) yes C7 . N6 . B11 . 123.00(18) yes N6 . C7 . N8 . 124.0(2) yes N6 . C7 . C29 . 108.98(19) yes N8 . C7 . C29 . 126.8(2) yes C7 . N8 . C9 . 120.27(19) yes N8 . C9 . N10 . 123.76(19) yes N8 . C9 . C22 . 127.5(2) yes N10 . C9 . C22 . 108.77(19) yes C9 . N10 . B11 . 122.25(18) yes C9 . N10 . C14 . 107.38(18) yes B11 . N10 . C14 . 130.26(19) yes N10 . B11 . N6 . 106.47(17) yes N10 . B11 . F12 . 109.54(18) yes N6 . B11 . F12 . 110.93(18) yes N10 . B11 . F13 . 109.81(18) yes N6 . B11 . F13 . 109.99(18) yes F12 . B11 . F13 . 110.03(18) yes N10 . C14 . C15 . 127.6(2) yes N10 . C14 . C21 . 109.36(19) yes C15 . C14 . C21 . 123.0(2) yes C14 . C15 . S16 . 126.46(18) yes C14 . C15 . C20 . 123.4(2) yes S16 . C15 . C20 . 110.14(18) yes C15 . S16 . C17 . 91.24(12) yes S16 . C17 . Br18 . 119.12(14) yes S16 . C17 . C19 . 113.50(19) yes Br18 . C17 . C19 . 127.33(19) yes C17 . C19 . C20 . 111.3(2) yes C17 . C19 . H191 . 125.5 no C20 . C19 . H191 . 123.2 no C19 . C20 . C15 . 113.8(2) yes C19 . C20 . H201 . 123.1 no C15 . C20 . H201 . 123.1 no C14 . C21 . C22 . 108.9(2) yes C14 . C21 . H211 . 125.6 no C22 . C21 . H211 . 125.5 no C9 . C22 . C21 . 105.6(2) yes C9 . C22 . C23 . 127.6(2) yes C21 . C22 . C23 . 126.7(2) yes C22 . C23 . C24 . 119.9(2) yes C22 . C23 . C28 . 122.1(2) yes C24 . C23 . C28 . 118.1(2) yes C23 . C24 . C25 . 121.5(2) yes C23 . C24 . H241 . 119.3 no C25 . C24 . H241 . 119.2 no C24 . C25 . C26 . 119.8(2) yes C24 . C25 . H251 . 119.8 no C26 . C25 . H251 . 120.4 no C25 . C26 . C27 . 119.4(2) yes C25 . C26 . H261 . 118.6 no C27 . C26 . H261 . 122.0 no C26 . C27 . C28 . 120.5(2) yes C26 . C27 . H271 . 120.2 no C28 . C27 . H271 . 119.3 no C23 . C28 . C27 . 120.7(2) yes C23 . C28 . H281 . 119.8 no C27 . C28 . H281 . 119.4 no C7 . C29 . C30 . 106.1(2) yes C7 . C29 . C31 . 127.0(2) yes C30 . C29 . C31 . 126.8(2) yes C5 . C30 . C29 . 108.6(2) yes C5 . C30 . H301 . 124.3 no C29 . C30 . H301 . 127.0 no C29 . C31 . C32 . 121.6(2) yes C29 . C31 . C36 . 118.8(2) yes C32 . C31 . C36 . 119.6(2) yes C31 . C32 . C33 . 120.6(2) yes C31 . C32 . H321 . 120.5 no C33 . C32 . H321 . 119.0 no C32 . C33 . C34 . 119.3(2) yes C32 . C33 . H331 . 121.2 no C34 . C33 . H331 . 119.5 no C33 . C34 . C35 . 120.5(2) yes C33 . C34 . H341 . 118.8 no C35 . C34 . H341 . 120.7 no C34 . C35 . C36 . 120.0(2) yes C34 . C35 . H351 . 122.1 no C36 . C35 . H351 . 117.9 no C31 . C36 . C35 . 120.0(2) yes C31 . C36 . H361 . 121.7 no C35 . C36 . H361 . 118.3 no C4 . C37 . C38 . 113.4(2) yes C4 . C37 . H371 . 123.1 no C38 . C37 . H371 . 123.5 no C37 . C38 . C2 . 112.1(2) yes C37 . C38 . H381 . 122.7 no C2 . C38 . H381 . 125.2 no Br39 . C40 . S41 . 120.90(14) yes Br39 . C40 . C76 . 125.48(19) yes S41 . C40 . C76 . 113.61(19) yes C40 . S41 . C42 . 91.05(12) yes S41 . C42 . C43 . 127.16(18) yes S41 . C42 . C75 . 109.79(18) yes C43 . C42 . C75 . 123.0(2) yes C42 . C43 . N44 . 127.9(2) yes C42 . C43 . C68 . 123.0(2) yes N44 . C43 . C68 . 109.1(2) yes C43 . N44 . C45 . 107.55(18) yes C43 . N44 . B49 . 129.83(19) yes C45 . N44 . B49 . 122.61(18) yes N44 . C45 . N46 . 123.7(2) yes N44 . C45 . C67 . 108.33(19) yes N46 . C45 . C67 . 128.0(2) yes C45 . N46 . C47 . 120.3(2) yes N46 . C47 . N48 . 123.7(2) yes N46 . C47 . C54 . 127.6(2) yes N48 . C47 . C54 . 108.69(19) yes C47 . N48 . B49 . 122.99(19) yes C47 . N48 . C52 . 107.76(18) yes B49 . N48 . C52 . 129.21(19) yes N44 . B49 . N48 . 106.68(18) yes N44 . B49 . F50 . 109.09(18) yes N48 . B49 . F50 . 111.21(18) yes N44 . B49 . F51 . 109.77(18) yes N48 . B49 . F51 . 110.01(18) yes F50 . B49 . F51 . 110.01(19) yes N48 . C52 . C53 . 108.78(19) yes N48 . C52 . C61 . 126.5(2) yes C53 . C52 . C61 . 124.8(2) yes C52 . C53 . C54 . 109.1(2) yes C52 . C53 . H531 . 124.7 no C54 . C53 . H531 . 126.2 no C47 . C54 . C53 . 105.6(2) yes C47 . C54 . C55 . 128.5(2) yes C53 . C54 . C55 . 125.9(2) yes C54 . C55 . C56 . 123.0(2) yes C54 . C55 . C60 . 119.2(2) yes C56 . C55 . C60 . 117.8(2) yes C55 . C56 . C57 . 121.3(2) yes C55 . C56 . H561 . 119.0 no C57 . C56 . H561 . 119.7 no C56 . C57 . C58 . 119.8(2) yes C56 . C57 . H571 . 120.0 no C58 . C57 . H571 . 120.2 no C57 . C58 . C59 . 119.9(2) yes C57 . C58 . H581 . 121.0 no C59 . C58 . H581 . 119.1 no C58 . C59 . C60 . 120.2(2) yes C58 . C59 . H591 . 120.8 no C60 . C59 . H591 . 118.9 no C55 . C60 . C59 . 121.0(2) yes C55 . C60 . H601 . 119.4 no C59 . C60 . H601 . 119.6 no C52 . C61 . S62 . 117.18(17) yes C52 . C61 . C66 . 132.0(2) yes S62 . C61 . C66 . 110.78(18) yes C61 . S62 . C63 . 91.05(11) yes S62 . C63 . Br64 . 119.42(14) yes S62 . C63 . C65 . 113.23(19) yes Br64 . C63 . C65 . 127.3(2) yes C63 . C65 . C66 . 111.6(2) yes C63 . C65 . H651 . 125.1 no C66 . C65 . H651 . 123.3 no C65 . C66 . C61 . 113.3(2) yes C65 . C66 . H661 . 122.5 no C61 . C66 . H661 . 124.2 no C45 . C67 . C68 . 106.0(2) yes C45 . C67 . C69 . 128.1(2) yes C68 . C67 . C69 . 125.9(2) yes C43 . C68 . C67 . 109.0(2) yes C43 . C68 . H681 . 125.9 no C67 . C68 . H681 . 125.1 no C67 . C69 . C70 . 122.3(2) yes C67 . C69 . C74 . 119.7(2) yes C70 . C69 . C74 . 118.0(2) yes C69 . C70 . C71 . 121.1(2) yes C69 . C70 . H701 . 119.5 no C71 . C70 . H701 . 119.4 no C70 . C71 . C72 . 120.2(2) yes C70 . C71 . H711 . 118.3 no C72 . C71 . H711 . 121.4 no C71 . C72 . C73 . 119.7(2) yes C71 . C72 . H721 . 118.9 no C73 . C72 . H721 . 121.4 no C72 . C73 . C74 . 119.9(2) yes C72 . C73 . H731 . 119.6 no C74 . C73 . H731 . 120.5 no C69 . C74 . C73 . 121.0(3) yes C69 . C74 . H741 . 118.9 no C73 . C74 . H741 . 120.0 no C42 . C75 . C76 . 114.5(2) yes C42 . C75 . H751 . 124.0 no C76 . C75 . H751 . 121.5 no C75 . C76 . C40 . 111.1(2) yes C75 . C76 . H761 . 125.3 no C40 . C76 . H761 . 123.6 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C28 . H281 . N8 . 128.00 0.92 2.37 3.020(3) yes C56 . H561 . N46 . 128.00 0.92 2.42 3.069(3) yes C70 . H701 . N46 . 128.00 0.94 2.38 3.054(3) yes _iucr_refine_instruction_details_constraints ; # # Punched on 21/07/11 at 13:55:46 # #LIST 12 BLOCK SCALE X'S, U'S CONT EXTPARAM RIDE C ( 19,X'S) H ( 191,X'S) RIDE C ( 20,X'S) H ( 201,X'S) RIDE C ( 21,X'S) H ( 211,X'S) RIDE C ( 24,X'S) H ( 241,X'S) RIDE C ( 25,X'S) H ( 251,X'S) RIDE C ( 26,X'S) H ( 261,X'S) RIDE C ( 27,X'S) H ( 271,X'S) RIDE C ( 28,X'S) H ( 281,X'S) RIDE C ( 30,X'S) H ( 301,X'S) RIDE C ( 32,X'S) H ( 321,X'S) RIDE C ( 33,X'S) H ( 331,X'S) RIDE C ( 34,X'S) H ( 341,X'S) RIDE C ( 35,X'S) H ( 351,X'S) RIDE C ( 36,X'S) H ( 361,X'S) RIDE C ( 37,X'S) H ( 371,X'S) RIDE C ( 38,X'S) H ( 381,X'S) RIDE C ( 53,X'S) H ( 531,X'S) RIDE C ( 56,X'S) H ( 561,X'S) RIDE C ( 57,X'S) H ( 571,X'S) RIDE C ( 58,X'S) H ( 581,X'S) RIDE C ( 59,X'S) H ( 591,X'S) RIDE C ( 60,X'S) H ( 601,X'S) RIDE C ( 65,X'S) H ( 651,X'S) RIDE C ( 66,X'S) H ( 661,X'S) RIDE C ( 68,X'S) H ( 681,X'S) RIDE C ( 70,X'S) H ( 701,X'S) RIDE C ( 71,X'S) H ( 711,X'S) RIDE C ( 72,X'S) H ( 721,X'S) RIDE C ( 73,X'S) H ( 731,X'S) RIDE C ( 74,X'S) H ( 741,X'S) RIDE C ( 75,X'S) H ( 751,X'S) RIDE C ( 76,X'S) H ( 761,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 21/07/11 at 13:55:46 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ;