# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Edwin Constable' 'Catherine E Housecroft' 'Markus Neuburger' 'Pirmin Rosel' _publ_contact_author_name 'Edwin Constable' _publ_contact_author_email EDWIN.CONSTABLE@UNIBAS.CH _publ_section_title ; Clicking hard-core sugar balls ; # Attachment 'publish.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 755189' #TrackingRef 'publish.cif' _audit_creation_date 09-08-11 _audit_creation_method CRYSTALS_ver_12.86 _oxford_structure_analysis_title 'pr392_123k_0m in P2(1)/n' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 13.0227(4) _cell_length_b 26.5826(8) _cell_length_c 15.1718(5) _cell_angle_alpha 90 _cell_angle_beta 106.5980(10) _cell_angle_gamma 90 _cell_volume 5033.3(3) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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' F 0.0171 0.0103 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' P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Ru -1.2594 0.8363 19.2674 0.8085 12.9182 8.4347 4.8634 24.7997 1.5676 94.2928 5.3787 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C50 H40 Cl2 F12 N6 O2 P2 Ru1 # Dc = 1.61 Fooo = 2456.00 Mu = 5.74 M = 1218.81 # Found Formula = C50 H40 Cl2 F12 N6 O2 P2 Ru1 # Dc = 1.61 FOOO = 2456.00 Mu = 5.74 M = 1218.81 _chemical_formula_sum 'C50 H40 Cl2 F12 N6 O2 P2 Ru1' _chemical_formula_moiety 'C48 H36 N6 O2 Ru, C2 H4 Cl2, 2(F6 P)' _chemical_compound_source ? _chemical_formula_weight 1218.81 _cell_measurement_reflns_used 9912 _cell_measurement_theta_min 3 _cell_measurement_theta_max 32089 _cell_measurement_temperature 123 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_max 0.19 _exptl_crystal_density_diffrn 1.608 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 2456 _exptl_absorpt_coefficient_mu 0.574 # Sheldrick geometric approximatio 0.93 0.96 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.93 _exptl_absorpt_correction_T_max 0.96 _diffrn_measurement_device 'Bruker Kappa Apex2' _diffrn_measurement_device_type Area _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 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _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 123 _diffrn_reflns_number 63295 _reflns_number_total 16714 _diffrn_reflns_av_R_equivalents 0.030 # Number of reflections with Friedels Law is 16714 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 16762 _diffrn_reflns_theta_min 1.596 _diffrn_reflns_theta_max 31.506 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 31.506 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -38 _diffrn_reflns_limit_k_max 39 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _reflns_limit_h_min -19 _reflns_limit_h_max 18 _reflns_limit_k_min 0 _reflns_limit_k_max 39 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _oxford_diffrn_Wilson_B_factor 1.53 _oxford_diffrn_Wilson_scale 198.81 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.87 _refine_diff_density_max 0.79 # 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>3.0\s(I) _refine_ls_number_reflns 11899 _refine_ls_number_restraints 0 _refine_ls_number_parameters 676 _oxford_refine_ls_R_factor_ref 0.0312 _refine_ls_wR_factor_ref 0.0341 _refine_ls_goodness_of_fit_ref 1.0861 _refine_ls_shift/su_max 0.001657 # The values computed from all data _oxford_reflns_number_all 16684 _refine_ls_R_factor_all 0.0468 _refine_ls_wR_factor_all 0.0587 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 13001 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_gt 0.0357 # 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: 0.161 0.114 0.473E-01 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. 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. 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. Bruker Analytical X-ray Systems, Inc., 2006. Apex2, Version 2 User Manual, M86-E01078, Madison, WI. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens Ru1 Ru 0.726700(10) 0.609439(4) 0.868698(8) 0.0149 1.0000 Uani . . . . . . . N1 N 0.76000(11) 0.67248(5) 0.95121(9) 0.0164 1.0000 Uani . . . . . . . N2 N 0.67385(11) 0.66574(5) 0.77168(9) 0.0171 1.0000 Uani . . . . . . . N3 N 0.58664(11) 0.60060(5) 0.90440(9) 0.0185 1.0000 Uani . . . . . . . N4 N 0.77577(11) 0.56129(5) 0.97907(9) 0.0172 1.0000 Uani . . . . . . . N5 N 0.86816(11) 0.60995(5) 0.83342(9) 0.0189 1.0000 Uani . . . . . . . N6 N 0.69908(12) 0.55305(5) 0.77151(9) 0.0188 1.0000 Uani . . . . . . . O1 O 1.07684(12) 0.64914(5) 1.37397(9) 0.0324 1.0000 Uani . . . . . . . O2 O 0.55048(12) 0.74562(5) 0.30123(8) 0.0311 1.0000 Uani . . . . . . . C1 C 0.80006(13) 0.67319(6) 1.04344(10) 0.0187 1.0000 Uani . . . . . . . C2 C 0.81956(13) 0.71740(6) 1.09516(11) 0.0194 1.0000 Uani . . . . . . . C3 C 0.79445(14) 0.76290(6) 1.04790(11) 0.0223 1.0000 Uani . . . . . . . C4 C 0.75318(14) 0.76279(6) 0.95322(11) 0.0216 1.0000 Uani . . . . . . . C5 C 0.73717(13) 0.71727(6) 0.90585(10) 0.0174 1.0000 Uani . . . . . . . C6 C 0.69377(13) 0.71341(6) 0.80577(10) 0.0173 1.0000 Uani . . . . . . . C7 C 0.67314(14) 0.75503(6) 0.74773(11) 0.0216 1.0000 Uani . . . . . . . C8 C 0.62739(15) 0.74841(6) 0.65423(11) 0.0224 1.0000 Uani . . . . . . . C9 C 0.60231(13) 0.69988(6) 0.61894(10) 0.0193 1.0000 Uani . . . . . . . C10 C 0.62868(13) 0.65978(6) 0.68079(10) 0.0181 1.0000 Uani . . . . . . . C11 C 0.49095(14) 0.62064(7) 0.86008(12) 0.0248 1.0000 Uani . . . . . . . C12 C 0.40053(15) 0.61387(8) 0.88926(14) 0.0295 1.0000 Uani . . . . . . . C13 C 0.40814(16) 0.58588(8) 0.96762(14) 0.0312 1.0000 Uani . . . . . . . C14 C 0.50605(16) 0.56480(7) 1.01393(13) 0.0277 1.0000 Uani . . . . . . . C15 C 0.59431(14) 0.57234(6) 0.98093(11) 0.0207 1.0000 Uani . . . . . . . C16 C 0.70145(13) 0.55141(6) 1.02430(11) 0.0191 1.0000 Uani . . . . . . . C17 C 0.72811(16) 0.52526(7) 1.10725(12) 0.0250 1.0000 Uani . . . . . . . C18 C 0.83271(16) 0.50983(7) 1.14580(12) 0.0278 1.0000 Uani . . . . . . . C19 C 0.90814(15) 0.51958(7) 1.09977(12) 0.0253 1.0000 Uani . . . . . . . C20 C 0.87674(14) 0.54491(6) 1.01635(11) 0.0208 1.0000 Uani . . . . . . . C21 C 0.95547(14) 0.63769(7) 0.87400(12) 0.0237 1.0000 Uani . . . . . . . C22 C 1.04768(15) 0.63644(7) 0.84604(14) 0.0286 1.0000 Uani . . . . . . . C23 C 1.05028(16) 0.60607(8) 0.77281(14) 0.0307 1.0000 Uani . . . . . . . C24 C 0.96129(16) 0.57741(7) 0.73026(13) 0.0279 1.0000 Uani . . . . . . . C25 C 0.87092(14) 0.57944(6) 0.76199(11) 0.0209 1.0000 Uani . . . . . . . C26 C 0.77412(14) 0.54901(6) 0.72487(11) 0.0206 1.0000 Uani . . . . . . . C27 C 0.75719(17) 0.51817(7) 0.64775(12) 0.0282 1.0000 Uani . . . . . . . C28 C 0.66380(18) 0.49014(7) 0.61960(13) 0.0331 1.0000 Uani . . . . . . . C29 C 0.59059(17) 0.49257(7) 0.66945(14) 0.0304 1.0000 Uani . . . . . . . C30 C 0.61058(15) 0.52443(6) 0.74488(12) 0.0234 1.0000 Uani . . . . . . . C31 C 0.86648(15) 0.71571(6) 1.19617(11) 0.0220 1.0000 Uani . . . . . . . C32 C 0.83599(18) 0.75113(7) 1.25163(12) 0.0307 1.0000 Uani . . . . . . . C33 C 0.8847(2) 0.75060(8) 1.34597(13) 0.0368 1.0000 Uani . . . . . . . C34 C 0.96344(19) 0.71574(8) 1.38505(13) 0.0348 1.0000 Uani . . . . . . . C35 C 0.99306(15) 0.68006(6) 1.32990(12) 0.0255 1.0000 Uani . . . . . . . C36 C 0.94475(14) 0.67960(6) 1.23558(11) 0.0223 1.0000 Uani . . . . . . . C37 C 1.07990(15) 0.59905(7) 1.33920(13) 0.0273 1.0000 Uani . . . . . . . C38 C 1.00689(16) 0.56538(7) 1.36715(14) 0.0293 1.0000 Uani . . . . . . . C39 C 0.9498(2) 0.53762(9) 1.39223(18) 0.0427 1.0000 Uani . . . . . . . C41 C 0.54893(13) 0.69115(6) 0.52023(11) 0.0200 1.0000 Uani . . . . . . . C42 C 0.47246(14) 0.65290(7) 0.49275(12) 0.0232 1.0000 Uani . . . . . . . C43 C 0.41927(15) 0.64664(7) 0.40018(12) 0.0257 1.0000 Uani . . . . . . . C44 C 0.44122(15) 0.67705(7) 0.33318(12) 0.0253 1.0000 Uani . . . . . . . C45 C 0.51869(15) 0.71449(6) 0.36057(11) 0.0233 1.0000 Uani . . . . . . . C46 C 0.57168(15) 0.72189(6) 0.45343(11) 0.0226 1.0000 Uani . . . . . . . C47 C 0.49051(18) 0.74243(8) 0.20598(12) 0.0330 1.0000 Uani . . . . . . . C48 C 0.53352(18) 0.78048(8) 0.15648(12) 0.0327 1.0000 Uani . . . . . . . C49 C 0.5661(2) 0.81187(9) 0.11608(14) 0.0400 1.0000 Uani . . . . . . . P1 P 0.27784(4) 0.572131(18) 0.62324(3) 0.0272 1.0000 Uani . . . . . . . F1 F 0.15162(11) 0.57292(6) 0.60950(12) 0.0522 1.0000 Uani . . . . . . . F2 F 0.40302(11) 0.57183(7) 0.63731(13) 0.0593 1.0000 Uani . . . . . . . F3 F 0.26360(14) 0.52037(5) 0.56687(11) 0.0507 1.0000 Uani . . . . . . . F4 F 0.29494(16) 0.54157(6) 0.71675(10) 0.0580 1.0000 Uani . . . . . . . F5 F 0.28845(13) 0.62420(5) 0.67859(10) 0.0475 1.0000 Uani . . . . . . . F6 F 0.26042(11) 0.60304(5) 0.52993(9) 0.0421 1.0000 Uani . . . . . . . P2 P 0.80238(4) 0.398013(17) 0.88212(3) 0.0237 1.0000 Uani . . . . . . . F7 F 0.68227(10) 0.41825(6) 0.85647(9) 0.0415 1.0000 Uani . . . . . . . F8 F 0.92331(10) 0.37701(5) 0.90695(9) 0.0375 1.0000 Uani . . . . . . . F9 F 0.82824(12) 0.42498(5) 0.97991(8) 0.0418 1.0000 Uani . . . . . . . F10 F 0.76722(12) 0.34844(5) 0.92610(11) 0.0456 1.0000 Uani . . . . . . . F11 F 0.77798(11) 0.37011(5) 0.78491(9) 0.0404 1.0000 Uani . . . . . . . F12 F 0.83866(11) 0.44725(5) 0.83830(9) 0.0387 1.0000 Uani . . . . . . . C51 C 0.2937(2) 0.39302(9) 0.58692(19) 0.0441 1.0000 Uani . . . . . . . C52 C 0.2750(2) 0.36616(11) 0.66750(18) 0.0472 1.0000 Uani . . . . . . . Cl1 Cl 0.19674(6) 0.37217(3) 0.48475(4) 0.0546 1.0000 Uani . . . . . . . Cl2 Cl 0.37401(8) 0.38484(4) 0.77015(6) 0.0831 1.0000 Uani . . . . . . . H11 H 0.8147 0.6423 1.0733 0.0230 1.0000 Uiso R . . . . . . H31 H 0.8055 0.7930 1.0798 0.0273 1.0000 Uiso R . . . . . . H41 H 0.7359 0.7929 0.9214 0.0259 1.0000 Uiso R . . . . . . H71 H 0.6885 0.7872 0.7709 0.0271 1.0000 Uiso R . . . . . . H81 H 0.6127 0.7761 0.6157 0.0261 1.0000 Uiso R . . . . . . H101 H 0.6147 0.6269 0.6581 0.0225 1.0000 Uiso R . . . . . . H111 H 0.4867 0.6394 0.8081 0.0298 1.0000 Uiso R . . . . . . H121 H 0.3354 0.6281 0.8553 0.0358 1.0000 Uiso R . . . . . . H131 H 0.3491 0.5815 0.9892 0.0397 1.0000 Uiso R . . . . . . H141 H 0.5137 0.5464 1.0663 0.0348 1.0000 Uiso R . . . . . . H171 H 0.6757 0.5185 1.1371 0.0320 1.0000 Uiso R . . . . . . H181 H 0.8516 0.4933 1.2011 0.0339 1.0000 Uiso R . . . . . . H191 H 0.9791 0.5092 1.1240 0.0307 1.0000 Uiso R . . . . . . H201 H 0.9253 0.5509 0.9845 0.0244 1.0000 Uiso R . . . . . . H211 H 0.9524 0.6581 0.9229 0.0283 1.0000 Uiso R . . . . . . H221 H 1.1064 0.6555 0.8761 0.0362 1.0000 Uiso R . . . . . . H231 H 1.1109 0.6051 0.7526 0.0396 1.0000 Uiso R . . . . . . H241 H 0.9613 0.5569 0.6810 0.0358 1.0000 Uiso R . . . . . . H271 H 0.8080 0.5164 0.6154 0.0360 1.0000 Uiso R . . . . . . H281 H 0.6514 0.4702 0.5673 0.0400 1.0000 Uiso R . . . . . . H291 H 0.5288 0.4740 0.6538 0.0359 1.0000 Uiso R . . . . . . H301 H 0.5611 0.5262 0.7777 0.0279 1.0000 Uiso R . . . . . . H321 H 0.7829 0.7748 1.2251 0.0369 1.0000 Uiso R . . . . . . H331 H 0.8634 0.7743 1.3842 0.0449 1.0000 Uiso R . . . . . . H341 H 0.9962 0.7160 1.4483 0.0414 1.0000 Uiso R . . . . . . H361 H 0.9655 0.6560 1.1981 0.0269 1.0000 Uiso R . . . . . . H371 H 1.1518 0.5870 1.3653 0.0328 1.0000 Uiso R . . . . . . H372 H 1.0643 0.5991 1.2736 0.0330 1.0000 Uiso R . . . . . . H391 H 0.9056 0.5160 1.4116 0.0548 1.0000 Uiso R . . . . . . H421 H 0.4564 0.6320 0.5367 0.0280 1.0000 Uiso R . . . . . . H431 H 0.3674 0.6216 0.3821 0.0306 1.0000 Uiso R . . . . . . H441 H 0.4062 0.6720 0.2720 0.0302 1.0000 Uiso R . . . . . . H461 H 0.6238 0.7474 0.4711 0.0275 1.0000 Uiso R . . . . . . H471 H 0.4149 0.7488 0.1990 0.0395 1.0000 Uiso R . . . . . . H472 H 0.4991 0.7097 0.1821 0.0393 1.0000 Uiso R . . . . . . H491 H 0.5908 0.8368 0.0840 0.0487 1.0000 Uiso R . . . . . . H511 H 0.2891 0.4289 0.5950 0.0545 1.0000 Uiso R . . . . . . H512 H 0.3652 0.3857 0.5812 0.0546 1.0000 Uiso R . . . . . . H521 H 0.2061 0.3743 0.6746 0.0573 1.0000 Uiso R . . . . . . H522 H 0.2815 0.3299 0.6586 0.0571 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 Ru1 0.01927(5) 0.01349(5) 0.01209(5) 0.00129(4) 0.00473(4) 0.00169(5) N1 0.0197(6) 0.0154(5) 0.0139(5) 0.0007(4) 0.0047(5) 0.0016(4) N2 0.0216(6) 0.0162(6) 0.0139(5) 0.0017(4) 0.0059(5) 0.0018(5) N3 0.0210(6) 0.0181(6) 0.0162(5) -0.0003(4) 0.0054(5) 0.0008(5) N4 0.0227(6) 0.0139(5) 0.0147(5) 0.0000(4) 0.0051(5) 0.0001(5) N5 0.0228(6) 0.0176(6) 0.0169(5) 0.0048(5) 0.0068(5) 0.0040(5) N6 0.0258(7) 0.0145(6) 0.0156(6) 0.0018(4) 0.0049(5) 0.0038(5) O1 0.0360(7) 0.0239(6) 0.0268(6) 0.0042(5) -0.0081(5) -0.0031(5) O2 0.0447(8) 0.0314(7) 0.0139(5) 0.0049(5) 0.0032(5) -0.0098(6) C1 0.0234(7) 0.0168(6) 0.0153(6) 0.0010(5) 0.0047(5) 0.0010(5) C2 0.0246(7) 0.0183(7) 0.0151(6) -0.0003(5) 0.0053(6) 0.0009(6) C3 0.0309(8) 0.0173(7) 0.0170(7) -0.0016(5) 0.0040(6) 0.0011(6) C4 0.0293(8) 0.0155(6) 0.0184(7) 0.0017(5) 0.0043(6) 0.0021(6) C5 0.0209(7) 0.0162(6) 0.0150(6) 0.0007(5) 0.0049(5) 0.0012(5) C6 0.0207(7) 0.0164(6) 0.0148(6) 0.0014(5) 0.0050(5) 0.0020(5) C7 0.0308(8) 0.0155(7) 0.0174(7) 0.0015(5) 0.0051(6) -0.0001(6) C8 0.0322(9) 0.0173(7) 0.0166(7) 0.0038(5) 0.0052(6) 0.0018(6) C9 0.0239(7) 0.0205(7) 0.0137(6) 0.0029(5) 0.0056(5) 0.0015(6) C10 0.0229(7) 0.0178(7) 0.0138(6) 0.0012(5) 0.0056(5) 0.0015(5) C11 0.0225(8) 0.0286(8) 0.0228(7) 0.0017(6) 0.0058(6) 0.0027(6) C12 0.0205(7) 0.0362(10) 0.0313(9) -0.0007(8) 0.0066(6) 0.0026(7) C13 0.0264(9) 0.0379(10) 0.0338(9) -0.0034(8) 0.0155(7) -0.0036(8) C14 0.0301(9) 0.0307(9) 0.0259(8) 0.0021(7) 0.0138(7) -0.0029(7) C15 0.0252(8) 0.0199(7) 0.0184(7) -0.0007(5) 0.0086(6) -0.0013(6) C16 0.0240(7) 0.0169(6) 0.0162(6) 0.0004(5) 0.0052(6) -0.0010(5) C17 0.0345(9) 0.0229(8) 0.0193(7) 0.0043(6) 0.0104(7) 0.0000(7) C18 0.0375(10) 0.0247(8) 0.0194(7) 0.0076(6) 0.0051(7) 0.0032(7) C19 0.0280(8) 0.0220(8) 0.0224(7) 0.0048(6) 0.0013(6) 0.0028(6) C20 0.0235(7) 0.0189(7) 0.0194(7) 0.0026(5) 0.0053(6) 0.0010(6) C21 0.0252(8) 0.0223(7) 0.0239(8) 0.0034(6) 0.0075(6) -0.0002(6) C22 0.0241(8) 0.0301(9) 0.0331(9) 0.0073(7) 0.0108(7) -0.0008(7) C23 0.0295(9) 0.0329(9) 0.0348(9) 0.0104(8) 0.0175(7) 0.0063(8) C24 0.0349(9) 0.0288(9) 0.0248(8) 0.0053(7) 0.0164(7) 0.0091(7) C25 0.0283(8) 0.0185(7) 0.0175(7) 0.0054(5) 0.0092(6) 0.0069(6) C26 0.0294(8) 0.0166(7) 0.0163(6) 0.0025(5) 0.0075(6) 0.0060(6) C27 0.0404(10) 0.0233(8) 0.0226(8) -0.0014(6) 0.0120(7) 0.0066(7) C28 0.0499(12) 0.0241(8) 0.0245(8) -0.0072(7) 0.0092(8) 0.0038(8) C29 0.0366(10) 0.0222(8) 0.0295(9) -0.0074(7) 0.0047(7) -0.0027(7) C30 0.0294(8) 0.0182(7) 0.0219(7) -0.0020(6) 0.0061(6) -0.0001(6) C31 0.0309(8) 0.0183(7) 0.0157(7) -0.0010(5) 0.0047(6) -0.0002(6) C32 0.0465(11) 0.0247(8) 0.0196(8) -0.0025(6) 0.0073(7) 0.0059(8) C33 0.0601(14) 0.0291(9) 0.0194(8) -0.0059(7) 0.0087(8) 0.0052(9) C34 0.0537(13) 0.0299(9) 0.0162(7) -0.0014(7) 0.0024(8) -0.0027(9) C35 0.0333(9) 0.0198(7) 0.0190(7) 0.0027(6) 0.0004(6) -0.0048(6) C36 0.0279(8) 0.0186(7) 0.0185(7) -0.0003(5) 0.0036(6) -0.0019(6) C37 0.0264(8) 0.0263(8) 0.0270(8) 0.0043(6) 0.0038(7) 0.0009(6) C38 0.0307(9) 0.0248(8) 0.0299(9) -0.0013(7) 0.0047(7) 0.0001(7) C39 0.0467(13) 0.0316(10) 0.0537(14) -0.0013(9) 0.0206(11) -0.0073(9) C41 0.0234(7) 0.0205(7) 0.0152(6) 0.0031(5) 0.0041(6) 0.0021(6) C42 0.0251(8) 0.0238(8) 0.0215(7) 0.0035(6) 0.0078(6) -0.0005(6) C43 0.0248(8) 0.0258(8) 0.0244(8) -0.0010(6) 0.0035(6) -0.0049(6) C44 0.0287(8) 0.0264(8) 0.0176(7) -0.0005(6) 0.0013(6) -0.0013(7) C45 0.0306(8) 0.0222(7) 0.0160(7) 0.0026(6) 0.0046(6) -0.0001(6) C46 0.0299(8) 0.0200(7) 0.0162(7) 0.0023(5) 0.0039(6) -0.0023(6) C47 0.0449(11) 0.0357(10) 0.0153(7) 0.0025(7) 0.0035(7) -0.0056(8) C48 0.0455(11) 0.0337(10) 0.0163(7) -0.0002(7) 0.0043(7) 0.0001(8) C49 0.0607(14) 0.0363(11) 0.0203(8) -0.0005(7) 0.0071(9) -0.0066(10) P1 0.0312(2) 0.0247(2) 0.0283(2) 0.00260(17) 0.01271(18) -0.00261(18) F1 0.0382(7) 0.0496(8) 0.0780(11) -0.0223(8) 0.0312(7) -0.0137(6) F2 0.0284(7) 0.0730(11) 0.0764(11) 0.0371(9) 0.0147(7) 0.0109(7) F3 0.0783(11) 0.0326(7) 0.0543(9) -0.0092(6) 0.0398(8) 0.0020(7) F4 0.0983(13) 0.0426(8) 0.0379(7) 0.0133(6) 0.0269(8) -0.0113(8) F5 0.0628(9) 0.0304(6) 0.0411(7) -0.0076(5) 0.0017(7) -0.0107(6) F6 0.0449(7) 0.0445(8) 0.0312(6) 0.0130(5) 0.0019(5) -0.0023(6) P2 0.0259(2) 0.0225(2) 0.02236(19) -0.00275(15) 0.00658(16) -0.00103(16) F7 0.0285(6) 0.0574(9) 0.0390(7) 0.0084(6) 0.0101(5) 0.0103(6) F8 0.0283(6) 0.0403(7) 0.0422(7) -0.0016(5) 0.0071(5) 0.0070(5) F9 0.0524(8) 0.0443(7) 0.0256(6) -0.0110(5) 0.0060(5) 0.0068(6) F10 0.0560(9) 0.0312(6) 0.0590(9) 0.0090(6) 0.0314(7) -0.0025(6) F11 0.0414(7) 0.0490(7) 0.0311(6) -0.0189(5) 0.0108(5) -0.0138(6) F12 0.0452(7) 0.0276(6) 0.0451(7) 0.0054(5) 0.0157(6) -0.0042(5) C51 0.0408(12) 0.0351(11) 0.0583(14) 0.0017(10) 0.0171(11) 0.0033(9) C52 0.0399(12) 0.0600(16) 0.0400(12) -0.0029(11) 0.0089(10) 0.0080(11) Cl1 0.0535(4) 0.0682(4) 0.0388(3) 0.0095(3) 0.0079(3) 0.0120(3) Cl2 0.0772(5) 0.1009(7) 0.0535(4) -0.0391(4) -0.0096(4) 0.0403(5) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.07197(5) 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 Ru1 . N1 . 2.0623(13) yes Ru1 . N2 . 2.0741(13) yes Ru1 . N3 . 2.0591(14) yes Ru1 . N4 . 2.0590(13) yes Ru1 . N5 . 2.0601(14) yes Ru1 . N6 . 2.0609(13) yes N1 . C1 . 1.3467(19) yes N1 . C5 . 1.3649(19) yes N2 . C6 . 1.365(2) yes N2 . C10 . 1.3451(19) yes N3 . C11 . 1.345(2) yes N3 . C15 . 1.363(2) yes N4 . C16 . 1.362(2) yes N4 . C20 . 1.347(2) yes N5 . C21 . 1.347(2) yes N5 . C25 . 1.362(2) yes N6 . C26 . 1.365(2) yes N6 . C30 . 1.343(2) yes O1 . C35 . 1.377(2) yes O1 . C37 . 1.437(2) yes O2 . C45 . 1.371(2) yes O2 . C47 . 1.435(2) yes C1 . C2 . 1.396(2) yes C1 . H11 . 0.931 no C2 . C3 . 1.396(2) yes C2 . C31 . 1.479(2) yes C3 . C4 . 1.382(2) yes C3 . H31 . 0.925 no C4 . C5 . 1.392(2) yes C4 . H41 . 0.928 no C5 . C6 . 1.465(2) yes C6 . C7 . 1.392(2) yes C7 . C8 . 1.384(2) yes C7 . H71 . 0.926 no C8 . C9 . 1.399(2) yes C8 . H81 . 0.926 no C9 . C10 . 1.397(2) yes C9 . C41 . 1.478(2) yes C10 . H101 . 0.937 no C11 . C12 . 1.383(3) yes C11 . H111 . 0.920 no C12 . C13 . 1.382(3) yes C12 . H121 . 0.938 no C13 . C14 . 1.386(3) yes C13 . H131 . 0.926 no C14 . C15 . 1.393(2) yes C14 . H141 . 0.914 no C15 . C16 . 1.471(2) yes C16 . C17 . 1.392(2) yes C17 . C18 . 1.382(3) yes C17 . H171 . 0.938 no C18 . C19 . 1.383(3) yes C18 . H181 . 0.916 no C19 . C20 . 1.388(2) yes C19 . H191 . 0.933 no C20 . H201 . 0.913 no C21 . C22 . 1.384(2) yes C21 . H211 . 0.930 no C22 . C23 . 1.381(3) yes C22 . H221 . 0.922 no C23 . C24 . 1.383(3) yes C23 . H231 . 0.926 no C24 . C25 . 1.394(2) yes C24 . H241 . 0.925 no C25 . C26 . 1.468(3) yes C26 . C27 . 1.394(2) yes C27 . C28 . 1.386(3) yes C27 . H271 . 0.932 no C28 . C29 . 1.377(3) yes C28 . H281 . 0.929 no C29 . C30 . 1.387(2) yes C29 . H291 . 0.916 no C30 . H301 . 0.921 no C31 . C32 . 1.394(2) yes C31 . C36 . 1.404(2) yes C32 . C33 . 1.390(3) yes C32 . H321 . 0.936 no C33 . C34 . 1.383(3) yes C33 . H331 . 0.950 no C34 . C35 . 1.390(3) yes C34 . H341 . 0.933 no C35 . C36 . 1.389(2) yes C36 . H361 . 0.937 no C37 . C38 . 1.454(3) yes C37 . H371 . 0.962 no C37 . H372 . 0.957 no C38 . C39 . 1.185(3) yes C39 . H391 . 0.919 no C41 . C42 . 1.401(2) yes C41 . C46 . 1.398(2) yes C42 . C43 . 1.387(2) yes C42 . H421 . 0.937 no C43 . C44 . 1.391(3) yes C43 . H431 . 0.933 no C44 . C45 . 1.393(2) yes C44 . H441 . 0.920 no C45 . C46 . 1.394(2) yes C46 . H461 . 0.944 no C47 . C48 . 1.463(3) yes C47 . H471 . 0.974 no C47 . H472 . 0.962 no C48 . C49 . 1.184(3) yes C49 . H491 . 0.932 no P1 . F1 . 1.5970(15) yes P1 . F2 . 1.5824(15) yes P1 . F3 . 1.6027(14) yes P1 . F4 . 1.5943(14) yes P1 . F5 . 1.6042(14) yes P1 . F6 . 1.5960(13) yes P2 . F7 . 1.5937(13) yes P2 . F8 . 1.6109(13) yes P2 . F9 . 1.5947(13) yes P2 . F10 . 1.6019(13) yes P2 . F11 . 1.5996(12) yes P2 . F12 . 1.5994(13) yes C51 . C52 . 1.495(4) yes C51 . Cl1 . 1.785(3) yes C51 . H511 . 0.965 no C51 . H512 . 0.978 no C52 . Cl2 . 1.786(3) yes C52 . H521 . 0.958 no C52 . H522 . 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 N1 . Ru1 . N2 . 79.28(5) yes N1 . Ru1 . N3 . 88.95(5) yes N2 . Ru1 . N3 . 97.45(5) yes N1 . Ru1 . N4 . 92.80(5) yes N2 . Ru1 . N4 . 171.41(5) yes N3 . Ru1 . N4 . 78.90(5) yes N1 . Ru1 . N5 . 95.95(5) yes N2 . Ru1 . N5 . 87.19(5) yes N3 . Ru1 . N5 . 173.82(5) yes N4 . Ru1 . N5 . 97.04(5) yes N1 . Ru1 . N6 . 171.39(5) yes N2 . Ru1 . N6 . 93.58(5) yes N3 . Ru1 . N6 . 96.80(5) yes N4 . Ru1 . N6 . 94.58(5) yes N5 . Ru1 . N6 . 78.77(6) yes Ru1 . N1 . C1 . 126.45(11) yes Ru1 . N1 . C5 . 115.15(10) yes C1 . N1 . C5 . 118.40(13) yes Ru1 . N2 . C6 . 114.35(10) yes Ru1 . N2 . C10 . 127.00(11) yes C6 . N2 . C10 . 118.55(13) yes Ru1 . N3 . C11 . 125.94(11) yes Ru1 . N3 . C15 . 115.62(11) yes C11 . N3 . C15 . 118.44(15) yes Ru1 . N4 . C16 . 115.43(11) yes Ru1 . N4 . C20 . 125.55(11) yes C16 . N4 . C20 . 118.37(13) yes Ru1 . N5 . C21 . 125.83(12) yes Ru1 . N5 . C25 . 115.56(11) yes C21 . N5 . C25 . 118.61(15) yes Ru1 . N6 . C26 . 115.07(11) yes Ru1 . N6 . C30 . 125.91(12) yes C26 . N6 . C30 . 118.65(14) yes C35 . O1 . C37 . 118.43(14) yes C45 . O2 . C47 . 116.47(15) yes N1 . C1 . C2 . 123.40(14) yes N1 . C1 . H11 . 117.3 no C2 . C1 . H11 . 119.3 no C1 . C2 . C3 . 117.54(14) yes C1 . C2 . C31 . 120.79(14) yes C3 . C2 . C31 . 121.67(14) yes C2 . C3 . C4 . 119.75(15) yes C2 . C3 . H31 . 120.1 no C4 . C3 . H31 . 120.1 no C3 . C4 . C5 . 119.65(15) yes C3 . C4 . H41 . 120.2 no C5 . C4 . H41 . 120.1 no C4 . C5 . N1 . 121.26(14) yes C4 . C5 . C6 . 123.55(14) yes N1 . C5 . C6 . 115.19(13) yes C5 . C6 . N2 . 115.66(13) yes C5 . C6 . C7 . 123.22(14) yes N2 . C6 . C7 . 121.12(14) yes C6 . C7 . C8 . 119.75(15) yes C6 . C7 . H71 . 120.9 no C8 . C7 . H71 . 119.3 no C7 . C8 . C9 . 119.65(14) yes C7 . C8 . H81 . 119.8 no C9 . C8 . H81 . 120.6 no C8 . C9 . C10 . 117.44(14) yes C8 . C9 . C41 . 121.55(14) yes C10 . C9 . C41 . 121.00(14) yes C9 . C10 . N2 . 123.40(15) yes C9 . C10 . H101 . 118.7 no N2 . C10 . H101 . 117.9 no N3 . C11 . C12 . 122.70(17) yes N3 . C11 . H111 . 117.6 no C12 . C11 . H111 . 119.7 no C11 . C12 . C13 . 119.15(17) yes C11 . C12 . H121 . 119.4 no C13 . C12 . H121 . 121.5 no C12 . C13 . C14 . 118.89(17) yes C12 . C13 . H131 . 120.6 no C14 . C13 . H131 . 120.5 no C13 . C14 . C15 . 119.58(17) yes C13 . C14 . H141 . 120.9 no C15 . C14 . H141 . 119.6 no C14 . C15 . N3 . 121.23(16) yes C14 . C15 . C16 . 124.01(15) yes N3 . C15 . C16 . 114.76(14) yes C15 . C16 . N4 . 114.91(13) yes C15 . C16 . C17 . 123.56(15) yes N4 . C16 . C17 . 121.47(15) yes C16 . C17 . C18 . 119.46(16) yes C16 . C17 . H171 . 120.3 no C18 . C17 . H171 . 120.2 no C17 . C18 . C19 . 119.15(16) yes C17 . C18 . H181 . 120.3 no C19 . C18 . H181 . 120.6 no C18 . C19 . C20 . 119.00(17) yes C18 . C19 . H191 . 120.8 no C20 . C19 . H191 . 120.2 no C19 . C20 . N4 . 122.52(16) yes C19 . C20 . H201 . 119.9 no N4 . C20 . H201 . 117.6 no N5 . C21 . C22 . 122.66(17) yes N5 . C21 . H211 . 117.5 no C22 . C21 . H211 . 119.9 no C21 . C22 . C23 . 118.91(18) yes C21 . C22 . H221 . 120.4 no C23 . C22 . H221 . 120.7 no C22 . C23 . C24 . 119.18(17) yes C22 . C23 . H231 . 120.2 no C24 . C23 . H231 . 120.6 no C23 . C24 . C25 . 119.66(17) yes C23 . C24 . H241 . 120.5 no C25 . C24 . H241 . 119.8 no C24 . C25 . N5 . 120.96(17) yes C24 . C25 . C26 . 124.29(16) yes N5 . C25 . C26 . 114.73(14) yes C25 . C26 . N6 . 114.93(14) yes C25 . C26 . C27 . 123.97(16) yes N6 . C26 . C27 . 121.10(17) yes C26 . C27 . C28 . 119.31(18) yes C26 . C27 . H271 . 120.4 no C28 . C27 . H271 . 120.3 no C27 . C28 . C29 . 119.34(17) yes C27 . C28 . H281 . 119.5 no C29 . C28 . H281 . 121.1 no C28 . C29 . C30 . 119.03(18) yes C28 . C29 . H291 . 121.8 no C30 . C29 . H291 . 119.1 no C29 . C30 . N6 . 122.46(17) yes C29 . C30 . H301 . 118.8 no N6 . C30 . H301 . 118.8 no C2 . C31 . C32 . 120.02(15) yes C2 . C31 . C36 . 119.79(15) yes C32 . C31 . C36 . 120.14(15) yes C31 . C32 . C33 . 119.32(18) yes C31 . C32 . H321 . 119.8 no C33 . C32 . H321 . 120.9 no C32 . C33 . C34 . 120.83(18) yes C32 . C33 . H331 . 119.6 no C34 . C33 . H331 . 119.5 no C33 . C34 . C35 . 119.86(17) yes C33 . C34 . H341 . 120.1 no C35 . C34 . H341 . 120.1 no C34 . C35 . O1 . 115.63(16) yes C34 . C35 . C36 . 120.27(17) yes O1 . C35 . C36 . 123.91(17) yes C31 . C36 . C35 . 119.54(16) yes C31 . C36 . H361 . 120.0 no C35 . C36 . H361 . 120.4 no O1 . C37 . C38 . 111.99(16) yes O1 . C37 . H371 . 106.5 no C38 . C37 . H371 . 108.4 no O1 . C37 . H372 . 111.2 no C38 . C37 . H372 . 109.9 no H371 . C37 . H372 . 108.7 no C37 . C38 . C39 . 178.0(2) yes C38 . C39 . H391 . 179.8 no C9 . C41 . C42 . 120.27(14) yes C9 . C41 . C46 . 120.47(15) yes C42 . C41 . C46 . 119.23(15) yes C41 . C42 . C43 . 119.70(15) yes C41 . C42 . H421 . 120.2 no C43 . C42 . H421 . 120.1 no C42 . C43 . C44 . 121.52(16) yes C42 . C43 . H431 . 119.6 no C44 . C43 . H431 . 118.9 no C43 . C44 . C45 . 118.66(15) yes C43 . C44 . H441 . 120.5 no C45 . C44 . H441 . 120.9 no C44 . C45 . O2 . 124.34(15) yes C44 . C45 . C46 . 120.61(15) yes O2 . C45 . C46 . 115.04(15) yes C41 . C46 . C45 . 120.26(16) yes C41 . C46 . H461 . 119.9 no C45 . C46 . H461 . 119.8 no O2 . C47 . C48 . 107.33(16) yes O2 . C47 . H471 . 110.0 no C48 . C47 . H471 . 110.3 no O2 . C47 . H472 . 110.1 no C48 . C47 . H472 . 109.2 no H471 . C47 . H472 . 109.9 no C47 . C48 . C49 . 178.4(3) yes C48 . C49 . H491 . 179.2 no F1 . P1 . F2 . 179.47(10) yes F1 . P1 . F3 . 89.07(8) yes F2 . P1 . F3 . 91.46(10) yes F1 . P1 . F4 . 89.99(10) yes F2 . P1 . F4 . 90.04(9) yes F3 . P1 . F4 . 90.17(8) yes F1 . P1 . F5 . 89.34(8) yes F2 . P1 . F5 . 90.14(10) yes F3 . P1 . F5 . 178.35(9) yes F4 . P1 . F5 . 90.26(8) yes F1 . P1 . F6 . 89.84(9) yes F2 . P1 . F6 . 90.13(8) yes F3 . P1 . F6 . 90.19(8) yes F4 . P1 . F6 . 179.61(9) yes F5 . P1 . F6 . 89.39(8) yes F7 . P2 . F8 . 179.23(8) yes F7 . P2 . F9 . 90.41(8) yes F8 . P2 . F9 . 90.33(7) yes F7 . P2 . F10 . 90.12(8) yes F8 . P2 . F10 . 89.66(8) yes F9 . P2 . F10 . 89.53(8) yes F7 . P2 . F11 . 90.50(8) yes F8 . P2 . F11 . 88.76(7) yes F9 . P2 . F11 . 178.90(8) yes F10 . P2 . F11 . 89.85(8) yes F7 . P2 . F12 . 90.46(7) yes F8 . P2 . F12 . 89.75(7) yes F9 . P2 . F12 . 90.57(8) yes F10 . P2 . F12 . 179.41(8) yes F11 . P2 . F12 . 90.04(7) yes C52 . C51 . Cl1 . 108.76(18) yes C52 . C51 . H511 . 109.7 no Cl1 . C51 . H511 . 111.3 no C52 . C51 . H512 . 111.0 no Cl1 . C51 . H512 . 108.4 no H511 . C51 . H512 . 107.7 no C51 . C52 . Cl2 . 109.5(2) yes C51 . C52 . H521 . 111.2 no Cl2 . C52 . H521 . 107.7 no C51 . C52 . H522 . 108.4 no Cl2 . C52 . H522 . 108.9 no H521 . C52 . H522 . 111.1 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 C4 . H41 . O1 4_464 137 0.93 2.52 3.259(3) yes C34 . H341 . C49 4_566 162 0.93 2.56 3.455(3) yes