# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global # 1. SUBMISSION DETAILS _journal_coden_Cambridge 177 _publ_requested_journal 'Organic and Biomolecular Chemistry' #============================================================================= # 2. TITLE AND AUTHOR LIST _publ_section_title ; Synthesis and antiplasmodial activity of streptocyanine/peroxide and streptocyanine/4-aminoquinoline hybrid dyes ; loop_ _publ_author_name 'Marie-Pierre Maether' 'Virginie Bernat' 'Marie Maturano' 'Christiane Andre-Barres' 'Sonia Ladeira' 'Alexis Valentin' 'Henri Viald' 'Corinne Payrastre' ; ; data_17b _database_code_depnum_ccdc_archive 'CCDC 805391' #TrackingRef 'CIF.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C39 H33 Cl2 F2 N6, B F4, 2(C H4 O)' _chemical_formula_sum 'C41 H41 B Cl2 F6 N6 O2' _chemical_formula_weight 845.51 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.6578(2) _cell_length_b 32.0622(6) _cell_length_c 12.1186(3) _cell_angle_alpha 90 _cell_angle_beta 100.604(1) _cell_angle_gamma 90 _cell_volume 4070.36(15) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 9716 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 30.62 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.22 _exptl_crystal_density_diffrn 1.38 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1752 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.231 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker-AXS)' _exptl_absorpt_correction_T_min 0.887 _exptl_absorpt_correction_T_max 0.952 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0368 _diffrn_reflns_av_unetI/netI 0.0242 _diffrn_reflns_number 134094 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -45 _diffrn_reflns_limit_k_max 46 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 31.21 _diffrn_reflns_theta_full 31.21 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 13147 _reflns_number_gt 9227 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0717P)^2^+1.9540P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 13147 _refine_ls_number_parameters 575 _refine_ls_number_restraints 50 _refine_ls_R_factor_all 0.082 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1581 _refine_ls_wR_factor_gt 0.1367 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.01 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.456 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.056 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.25206(18) 0.16321(5) 0.74138(13) 0.0333(3) Uani 1 1 d . . . C2 C 0.14925(17) 0.14519(5) 0.67546(14) 0.0334(3) Uani 1 1 d . . . H2 H 0.0699 0.1595 0.6606 0.04 Uiso 1 1 calc R . . C3 C 0.16042(15) 0.10513(5) 0.62889(13) 0.0285(3) Uani 1 1 d . . . C4 C 0.27944(14) 0.08387(4) 0.65285(12) 0.0257(3) Uani 1 1 d . . . C5 C 0.38325(16) 0.10408(5) 0.72173(14) 0.0319(3) Uani 1 1 d . . . H5 H 0.4636 0.0904 0.7381 0.038 Uiso 1 1 calc R . . C6 C 0.37051(17) 0.14304(5) 0.76552(14) 0.0348(3) Uani 1 1 d . . . H6 H 0.4412 0.1561 0.8117 0.042 Uiso 1 1 calc R . . C7 C 0.06865(17) 0.05211(6) 0.51620(15) 0.0375(4) Uani 1 1 d . . . H7 H -0.0032 0.0409 0.467 0.045 Uiso 1 1 calc R . . C8 C 0.17925(16) 0.02810(5) 0.53460(14) 0.0336(3) Uani 1 1 d . . . H8 H 0.1806 0.0018 0.499 0.04 Uiso 1 1 calc R . . C9 C 0.28774(14) 0.04287(5) 0.60540(13) 0.0272(3) Uani 1 1 d . . . C10 C 0.41748(17) -0.02135(5) 0.59081(15) 0.0350(3) Uani 1 1 d . . . H10A H 0.5056 -0.0238 0.5761 0.042 Uiso 1 1 calc R . . H10B H 0.3578 -0.0263 0.5192 0.042 Uiso 1 1 calc R . . C11 C 0.39628(16) -0.05470(5) 0.67622(15) 0.0334(3) Uani 1 1 d . . . H11A H 0.4575 -0.0502 0.7472 0.04 Uiso 1 1 calc R . . H11B H 0.309 -0.0518 0.6924 0.04 Uiso 1 1 calc R . . C12 C 0.52476(14) -0.11607(5) 0.64023(13) 0.0269(3) Uani 1 1 d . . . C13 C 0.64137(14) -0.09642(5) 0.68002(13) 0.0287(3) Uani 1 1 d . . . H13 H 0.6401 -0.0673 0.6949 0.034 Uiso 1 1 calc R . . C14 C 0.75922(14) -0.11650(5) 0.69937(13) 0.0272(3) Uani 1 1 d . . . H14 H 0.7628 -0.1455 0.6848 0.033 Uiso 1 1 calc R . . C15 C 0.87161(14) -0.09506(5) 0.73941(14) 0.0288(3) Uani 1 1 d . . . H15 H 0.8649 -0.0659 0.7512 0.035 Uiso 1 1 calc R . . C16 C 0.99402(14) -0.11255(4) 0.76403(13) 0.0258(3) Uani 1 1 d . . . C17 C 1.08258(15) -0.04996(5) 0.87290(13) 0.0281(3) Uani 1 1 d . . . H17A H 1.1549 -0.0466 0.9365 0.034 Uiso 1 1 calc R . . H17B H 1.0026 -0.0488 0.9033 0.034 Uiso 1 1 calc R . . C18 C 1.08386(14) -0.01385(4) 0.78992(13) 0.0263(3) Uani 1 1 d . . . H18A H 1.1588 -0.0169 0.7529 0.032 Uiso 1 1 calc R . . H18B H 1.0061 -0.0154 0.7311 0.032 Uiso 1 1 calc R . . C19 C 1.19786(13) 0.04470(4) 0.89866(12) 0.0235(3) Uani 1 1 d . . . C20 C 1.31736(14) 0.02599(5) 0.90824(14) 0.0287(3) Uani 1 1 d . . . H20 H 1.3254 -0.0007 0.8764 0.034 Uiso 1 1 calc R . . C21 C 1.42525(15) 0.04681(5) 0.96503(15) 0.0331(3) Uani 1 1 d . . . H21 H 1.5054 0.0335 0.9682 0.04 Uiso 1 1 calc R . . C22 C 1.19374(13) 0.08560(4) 0.94727(12) 0.0233(3) Uani 1 1 d . . . C23 C 1.30973(14) 0.10310(5) 1.00562(13) 0.0261(3) Uani 1 1 d . . . C24 C 1.30840(16) 0.14294(5) 1.05534(13) 0.0307(3) Uani 1 1 d . . . H24 H 1.3852 0.1547 1.0955 0.037 Uiso 1 1 calc R . . C25 C 1.19650(17) 0.16428(5) 1.04540(14) 0.0312(3) Uani 1 1 d . . . C26 C 1.08127(16) 0.14843(5) 0.98474(14) 0.0313(3) Uani 1 1 d . . . H26 H 1.005 0.1644 0.9767 0.038 Uiso 1 1 calc R . . C27 C 1.08048(14) 0.10954(4) 0.93725(13) 0.0270(3) Uani 1 1 d . . . H27 H 1.0027 0.0985 0.897 0.032 Uiso 1 1 calc R . . C28 C 0.51479(14) -0.15994(5) 0.59978(14) 0.0296(3) Uani 1 1 d . . . C29 C 0.43371(18) -0.18755(6) 0.6416(2) 0.0468(5) Uani 1 1 d . . . H29 H 0.3883 -0.1786 0.6979 0.056 Uiso 1 1 calc R . . C30 C 0.4194(2) -0.22809(6) 0.6011(3) 0.0631(7) Uani 1 1 d . . . H30 H 0.3653 -0.2472 0.6298 0.076 Uiso 1 1 calc R . . C31 C 0.4846(2) -0.23996(6) 0.5190(3) 0.0595(6) Uani 1 1 d . . . C32 C 0.5646(2) -0.21395(6) 0.4754(2) 0.0485(5) Uani 1 1 d . . . H32 H 0.6083 -0.2232 0.4184 0.058 Uiso 1 1 calc R . . C33 C 0.57992(16) -0.17348(5) 0.51724(16) 0.0352(3) Uani 1 1 d . . . H33 H 0.6357 -0.1549 0.4889 0.042 Uiso 1 1 calc R . . C34 C 1.02446(14) -0.15557(5) 0.73106(14) 0.0289(3) Uani 1 1 d . . . C35 C 0.97407(17) -0.17124(5) 0.62504(16) 0.0377(4) Uani 1 1 d . . . H35 H 0.9185 -0.1544 0.573 0.045 Uiso 1 1 calc R . . C36 C 1.0042(2) -0.21129(6) 0.5944(2) 0.0512(5) Uani 1 1 d . . . H36 H 0.9695 -0.2221 0.5222 0.061 Uiso 1 1 calc R . . C37 C 1.0849(2) -0.23485(6) 0.6707(2) 0.0537(6) Uani 1 1 d . . . C38 C 1.13724(19) -0.22077(6) 0.7755(2) 0.0502(5) Uani 1 1 d . . . H38 H 1.193 -0.2379 0.8264 0.06 Uiso 1 1 calc R . . C39 C 1.10687(16) -0.18074(5) 0.80576(17) 0.0375(4) Uani 1 1 d . . . H39 H 1.1426 -0.1704 0.8782 0.045 Uiso 1 1 calc R . . C40 C 0.6874(2) 0.12824(7) -0.0335(2) 0.0534(5) Uani 1 1 d . . . H40A H 0.6656 0.1578 -0.0463 0.08 Uiso 1 1 calc R . . H40B H 0.6347 0.1113 -0.0916 0.08 Uiso 1 1 calc R . . H40C H 0.7778 0.124 -0.0366 0.08 Uiso 1 1 calc R . . C41 C 0.7797(3) 0.14111(14) 0.6121(3) 0.1026(13) Uani 1 1 d . . . H41A H 0.8297 0.1268 0.6771 0.154 Uiso 1 1 calc R . . H41B H 0.6885 0.1377 0.6128 0.154 Uiso 1 1 calc R . . H41C H 0.8011 0.1709 0.6155 0.154 Uiso 1 1 calc R . . N1 N 0.05416(13) 0.08907(5) 0.56092(13) 0.0359(3) Uani 1 1 d . . . N2 N 0.39804(14) 0.02067(4) 0.62994(13) 0.0349(3) Uani 1 1 d D . . H200 H 0.4618(15) 0.0307(6) 0.6762(15) 0.042 Uiso 1 1 d D . . N3 N 0.41261(13) -0.09669(4) 0.63541(13) 0.0321(3) Uani 1 1 d D . . H300 H 0.3458(14) -0.1094(6) 0.6009(16) 0.039 Uiso 1 1 d D . . N4 N 1.09222(12) -0.09071(4) 0.82055(12) 0.0289(3) Uani 1 1 d D . . H400 H 1.1669(11) -0.1014(6) 0.8357(16) 0.035 Uiso 1 1 d D . . N5 N 1.08895(12) 0.02644(4) 0.84435(12) 0.0279(3) Uani 1 1 d D . . H500 H 1.0177(12) 0.0386(6) 0.8467(17) 0.033 Uiso 1 1 d D . . N6 N 1.42535(12) 0.08354(4) 1.01481(12) 0.0326(3) Uani 1 1 d . . . F1 F 0.46788(17) -0.27934(4) 0.4777(2) 0.0965(7) Uani 1 1 d . . . F2 F 1.11647(15) -0.27384(4) 0.64056(17) 0.0841(5) Uani 1 1 d . . . Cl1 Cl 0.23723(6) 0.212405(13) 0.79810(4) 0.04834(14) Uani 1 1 d . . . Cl2 Cl 1.19501(5) 0.212404(13) 1.11123(4) 0.04505(12) Uani 1 1 d . . . O1 O 0.66447(12) 0.11606(5) 0.07416(13) 0.0505(4) Uani 1 1 d . . . H1 H 0.5895 0.1071 0.068 0.076 Uiso 1 1 calc R . . O2 O 0.80824(14) 0.12382(6) 0.51240(15) 0.0627(5) Uani 1 1 d . . . H2A H 0.8775 0.1107 0.5272 0.094 Uiso 1 1 calc R . . B1 B 0.7384(2) 0.02808(8) 0.7795(2) 0.0520(6) Uani 1 1 d D . . F3 F 0.8227(5) 0.05927(13) 0.8123(4) 0.0901(16) Uani 0.61 1 d PDU A 1 F4 F 0.7394(5) 0.0111(2) 0.6809(4) 0.0921(16) Uani 0.61 1 d PDU A 1 F5 F 0.6243(2) 0.03489(11) 0.8074(3) 0.0752(8) Uani 0.61 1 d PDU A 1 F6 F 0.7964(3) -0.00565(11) 0.8570(3) 0.0948(9) Uani 0.61 1 d PDU A 1 F3' F 0.8233(7) 0.0454(2) 0.8539(5) 0.0710(18) Uani 0.39 1 d PDU A 2 F4' F 0.7866(8) 0.0101(4) 0.6984(8) 0.099(3) Uani 0.39 1 d PDU A 2 F5' F 0.6472(6) 0.0040(2) 0.8087(5) 0.1078(17) Uani 0.39 1 d PDU A 2 F6' F 0.6563(4) 0.06171(14) 0.7100(5) 0.0930(15) Uani 0.39 1 d PDU A 2 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 0.0506(10) 0.0218(6) 0.0275(7) 0.0033(5) 0.0070(7) 0.0026(6) C2 0.0389(9) 0.0288(7) 0.0321(8) 0.0044(6) 0.0054(6) 0.0095(6) C3 0.0293(7) 0.0270(7) 0.0281(7) 0.0038(5) 0.0023(6) 0.0036(6) C4 0.0270(7) 0.0243(6) 0.0253(7) 0.0028(5) 0.0038(5) 0.0015(5) C5 0.0301(7) 0.0295(7) 0.0338(8) 0.0023(6) 0.0003(6) 0.0014(6) C6 0.0401(9) 0.0278(7) 0.0337(8) 0.0012(6) -0.0011(7) -0.0041(6) C7 0.0312(8) 0.0406(9) 0.0373(9) -0.0029(7) -0.0026(7) -0.0013(7) C8 0.0360(8) 0.0293(7) 0.0342(8) -0.0048(6) 0.0032(7) -0.0007(6) C9 0.0288(7) 0.0255(7) 0.0275(7) 0.0019(5) 0.0059(6) 0.0029(5) C10 0.0387(9) 0.0300(7) 0.0371(8) -0.0014(6) 0.0091(7) 0.0100(6) C11 0.0308(8) 0.0303(7) 0.0414(9) -0.0028(6) 0.0130(7) 0.0063(6) C12 0.0238(7) 0.0255(7) 0.0321(7) 0.0027(5) 0.0068(6) 0.0017(5) C13 0.0242(7) 0.0259(7) 0.0347(8) 0.0010(6) 0.0026(6) 0.0009(5) C14 0.0253(7) 0.0260(7) 0.0297(7) 0.0028(5) 0.0030(6) 0.0000(5) C15 0.0248(7) 0.0241(6) 0.0363(8) 0.0009(6) 0.0022(6) 0.0005(5) C16 0.0240(7) 0.0215(6) 0.0314(7) 0.0010(5) 0.0040(5) -0.0013(5) C17 0.0282(7) 0.0235(6) 0.0314(7) -0.0034(5) 0.0029(6) -0.0010(5) C18 0.0259(7) 0.0219(6) 0.0309(7) -0.0043(5) 0.0047(6) -0.0013(5) C19 0.0223(6) 0.0215(6) 0.0266(7) 0.0018(5) 0.0040(5) -0.0009(5) C20 0.0237(7) 0.0238(6) 0.0381(8) 0.0010(6) 0.0044(6) 0.0026(5) C21 0.0224(7) 0.0298(7) 0.0451(9) 0.0068(6) 0.0012(6) 0.0031(6) C22 0.0224(6) 0.0206(6) 0.0267(7) 0.0022(5) 0.0039(5) -0.0015(5) C23 0.0239(7) 0.0255(6) 0.0274(7) 0.0036(5) 0.0009(5) -0.0035(5) C24 0.0345(8) 0.0266(7) 0.0296(7) 0.0002(6) 0.0024(6) -0.0091(6) C25 0.0421(9) 0.0209(6) 0.0318(8) -0.0020(5) 0.0099(6) -0.0051(6) C26 0.0329(8) 0.0241(7) 0.0379(8) -0.0011(6) 0.0089(6) 0.0018(6) C27 0.0246(7) 0.0229(6) 0.0332(7) -0.0008(5) 0.0042(6) -0.0004(5) C28 0.0216(6) 0.0242(7) 0.0420(9) 0.0022(6) 0.0029(6) 0.0016(5) C29 0.0372(9) 0.0315(8) 0.0766(14) 0.0029(9) 0.0236(9) -0.0011(7) C30 0.0496(12) 0.0288(9) 0.117(2) 0.0014(11) 0.0308(13) -0.0086(8) C31 0.0456(11) 0.0250(8) 0.108(2) -0.0137(10) 0.0141(12) -0.0018(8) C32 0.0416(10) 0.0366(9) 0.0681(14) -0.0129(9) 0.0122(9) 0.0032(8) C33 0.0301(8) 0.0303(8) 0.0455(9) -0.0023(7) 0.0077(7) 0.0008(6) C34 0.0244(7) 0.0222(6) 0.0404(8) -0.0024(6) 0.0070(6) -0.0029(5) C35 0.0371(9) 0.0322(8) 0.0435(9) -0.0063(7) 0.0064(7) -0.0025(7) C36 0.0507(11) 0.0394(10) 0.0631(13) -0.0229(9) 0.0091(10) -0.0063(8) C37 0.0426(10) 0.0271(8) 0.0918(17) -0.0184(9) 0.0137(11) -0.0010(7) C38 0.0392(10) 0.0255(8) 0.0824(16) -0.0022(9) 0.0021(10) 0.0055(7) C39 0.0305(8) 0.0265(7) 0.0528(10) -0.0021(7) 0.0006(7) 0.0016(6) C40 0.0368(10) 0.0546(12) 0.0636(14) -0.0080(10) -0.0043(9) -0.0010(9) C41 0.0616(18) 0.152(4) 0.088(2) -0.023(2) -0.0028(16) 0.033(2) N1 0.0290(7) 0.0375(7) 0.0385(8) 0.0002(6) -0.0011(6) 0.0051(5) N2 0.0335(7) 0.0274(6) 0.0419(8) -0.0030(6) 0.0022(6) 0.0071(5) N3 0.0229(6) 0.0277(6) 0.0462(8) -0.0026(6) 0.0078(6) 0.0022(5) N4 0.0217(6) 0.0233(6) 0.0401(7) -0.0028(5) 0.0012(5) 0.0007(4) N5 0.0216(6) 0.0221(6) 0.0391(7) -0.0059(5) 0.0034(5) 0.0011(4) N6 0.0234(6) 0.0306(6) 0.0406(7) 0.0041(5) -0.0020(5) -0.0026(5) F1 0.0865(12) 0.0322(7) 0.178(2) -0.0351(9) 0.0433(12) -0.0124(7) F2 0.0747(10) 0.0350(7) 0.1391(15) -0.0359(8) 0.0108(10) 0.0077(6) Cl1 0.0808(4) 0.02265(18) 0.0411(2) 0.00044(15) 0.0100(2) 0.00536(19) Cl2 0.0588(3) 0.02487(19) 0.0531(3) -0.01116(17) 0.0146(2) -0.00746(17) O1 0.0232(6) 0.0592(9) 0.0632(9) 0.0016(7) -0.0070(6) -0.0056(6) O2 0.0289(7) 0.0888(13) 0.0659(10) -0.0070(9) -0.0035(7) 0.0106(7) B1 0.0348(11) 0.0601(14) 0.0622(15) -0.0268(12) 0.0119(10) -0.0018(10) F3 0.0476(16) 0.063(2) 0.150(5) -0.026(2) -0.008(3) -0.0042(14) F4 0.109(4) 0.127(3) 0.0381(16) -0.0206(18) 0.008(2) -0.008(3) F5 0.0308(10) 0.101(2) 0.0928(19) -0.0247(18) 0.0080(11) 0.0123(12) F6 0.096(2) 0.105(2) 0.0875(19) 0.0232(17) 0.0262(16) 0.0438(17) F3' 0.0381(19) 0.112(5) 0.058(3) -0.042(3) -0.005(2) 0.004(3) F4' 0.090(5) 0.129(4) 0.071(4) -0.051(3) 0.000(3) 0.043(4) F5' 0.101(4) 0.125(4) 0.101(3) -0.011(3) 0.027(3) -0.038(3) F6' 0.058(2) 0.070(3) 0.136(4) -0.013(3) -0.023(2) 0.029(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.360(2) . ? C1 C6 1.401(2) . ? C1 Cl1 1.7394(16) . ? C2 C3 1.417(2) . ? C2 H2 0.95 . ? C3 N1 1.372(2) . ? C3 C4 1.422(2) . ? C4 C5 1.414(2) . ? C4 C9 1.444(2) . ? C5 C6 1.374(2) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 N1 1.324(2) . ? C7 C8 1.391(2) . ? C7 H7 0.95 . ? C8 C9 1.390(2) . ? C8 H8 0.95 . ? C9 N2 1.360(2) . ? C10 N2 1.456(2) . ? C10 C11 1.534(2) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 N3 1.456(2) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 N3 1.3389(19) . ? C12 C13 1.398(2) . ? C12 C28 1.487(2) . ? C13 C14 1.392(2) . ? C13 H13 0.95 . ? C14 C15 1.389(2) . ? C14 H14 0.95 . ? C15 C16 1.401(2) . ? C15 H15 0.95 . ? C16 N4 1.3382(19) . ? C16 C34 1.488(2) . ? C17 N4 1.4644(19) . ? C17 C18 1.535(2) . ? C17 H17A 0.99 . ? C17 H17B 0.99 . ? C18 N5 1.4469(18) . ? C18 H18A 0.99 . ? C18 H18B 0.99 . ? C19 N5 1.3573(18) . ? C19 C20 1.393(2) . ? C19 C22 1.4416(19) . ? C20 C21 1.396(2) . ? C20 H20 0.95 . ? C21 N6 1.323(2) . ? C21 H21 0.95 . ? C22 C27 1.417(2) . ? C22 C23 1.4216(19) . ? C23 N6 1.369(2) . ? C23 C24 1.414(2) . ? C24 C25 1.361(2) . ? C24 H24 0.95 . ? C25 C26 1.405(2) . ? C25 Cl2 1.7385(16) . ? C26 C27 1.373(2) . ? C26 H26 0.95 . ? C27 H27 0.95 . ? C28 C33 1.388(2) . ? C28 C29 1.396(2) . ? C29 C30 1.388(3) . ? C29 H29 0.95 . ? C30 C31 1.368(4) . ? C30 H30 0.95 . ? C31 F1 1.358(2) . ? C31 C32 1.366(3) . ? C32 C33 1.392(2) . ? C32 H32 0.95 . ? C33 H33 0.95 . ? C34 C35 1.392(2) . ? C34 C39 1.396(2) . ? C35 C36 1.391(3) . ? C35 H35 0.95 . ? C36 C37 1.368(3) . ? C36 H36 0.95 . ? C37 F2 1.362(2) . ? C37 C38 1.367(3) . ? C38 C39 1.389(2) . ? C38 H38 0.95 . ? C39 H39 0.95 . ? C40 O1 1.425(3) . ? C40 H40A 0.98 . ? C40 H40B 0.98 . ? C40 H40C 0.98 . ? C41 O2 1.412(4) . ? C41 H41A 0.98 . ? C41 H41B 0.98 . ? C41 H41C 0.98 . ? N2 H200 0.860(10) . ? N3 H300 0.860(9) . ? N4 H400 0.855(9) . ? N5 H500 0.858(9) . ? O1 H1 0.84 . ? O2 H2A 0.84 . ? B1 F3' 1.281(6) . ? B1 F4 1.315(5) . ? B1 F4' 1.322(8) . ? B1 F5 1.338(3) . ? B1 F5' 1.338(6) . ? B1 F3 1.354(5) . ? B1 F6 1.490(4) . ? B1 F6' 1.538(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 121.61(15) . . ? C2 C1 Cl1 119.69(13) . . ? C6 C1 Cl1 118.70(13) . . ? C1 C2 C3 120.10(15) . . ? C1 C2 H2 120 . . ? C3 C2 H2 120 . . ? N1 C3 C2 117.31(14) . . ? N1 C3 C4 123.32(14) . . ? C2 C3 C4 119.37(14) . . ? C5 C4 C3 118.19(14) . . ? C5 C4 C9 123.60(14) . . ? C3 C4 C9 118.21(13) . . ? C6 C5 C4 121.49(15) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C1 119.25(15) . . ? C5 C6 H6 120.4 . . ? C1 C6 H6 120.4 . . ? N1 C7 C8 126.07(15) . . ? N1 C7 H7 117 . . ? C8 C7 H7 117 . . ? C9 C8 C7 119.65(15) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? N2 C9 C8 122.96(14) . . ? N2 C9 C4 120.23(14) . . ? C8 C9 C4 116.81(13) . . ? N2 C10 C11 112.21(14) . . ? N2 C10 H10A 109.2 . . ? C11 C10 H10A 109.2 . . ? N2 C10 H10B 109.2 . . ? C11 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? N3 C11 C10 111.95(14) . . ? N3 C11 H11A 109.2 . . ? C10 C11 H11A 109.2 . . ? N3 C11 H11B 109.2 . . ? C10 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? N3 C12 C13 122.39(14) . . ? N3 C12 C28 114.56(13) . . ? C13 C12 C28 123.05(13) . . ? C14 C13 C12 124.53(14) . . ? C14 C13 H13 117.7 . . ? C12 C13 H13 117.7 . . ? C15 C14 C13 121.55(14) . . ? C15 C14 H14 119.2 . . ? C13 C14 H14 119.2 . . ? C14 C15 C16 125.86(14) . . ? C14 C15 H15 117.1 . . ? C16 C15 H15 117.1 . . ? N4 C16 C15 120.63(13) . . ? N4 C16 C34 115.70(13) . . ? C15 C16 C34 123.66(13) . . ? N4 C17 C18 112.29(13) . . ? N4 C17 H17A 109.1 . . ? C18 C17 H17A 109.1 . . ? N4 C17 H17B 109.1 . . ? C18 C17 H17B 109.1 . . ? H17A C17 H17B 107.9 . . ? N5 C18 C17 112.26(13) . . ? N5 C18 H18A 109.2 . . ? C17 C18 H18A 109.2 . . ? N5 C18 H18B 109.2 . . ? C17 C18 H18B 109.2 . . ? H18A C18 H18B 107.9 . . ? N5 C19 C20 122.81(13) . . ? N5 C19 C22 120.19(12) . . ? C20 C19 C22 116.99(13) . . ? C19 C20 C21 119.50(14) . . ? C19 C20 H20 120.2 . . ? C21 C20 H20 120.2 . . ? N6 C21 C20 125.57(14) . . ? N6 C21 H21 117.2 . . ? C20 C21 H21 117.2 . . ? C27 C22 C23 118.56(13) . . ? C27 C22 C19 123.18(13) . . ? C23 C22 C19 118.23(13) . . ? N6 C23 C24 117.31(13) . . ? N6 C23 C22 123.17(14) . . ? C24 C23 C22 119.51(14) . . ? C25 C24 C23 119.59(14) . . ? C25 C24 H24 120.2 . . ? C23 C24 H24 120.2 . . ? C24 C25 C26 122.13(14) . . ? C24 C25 Cl2 119.17(12) . . ? C26 C25 Cl2 118.69(13) . . ? C27 C26 C25 119.02(14) . . ? C27 C26 H26 120.5 . . ? C25 C26 H26 120.5 . . ? C26 C27 C22 121.11(14) . . ? C26 C27 H27 119.4 . . ? C22 C27 H27 119.4 . . ? C33 C28 C29 119.25(16) . . ? C33 C28 C12 121.23(14) . . ? C29 C28 C12 119.44(15) . . ? C30 C29 C28 120.0(2) . . ? C30 C29 H29 120 . . ? C28 C29 H29 120 . . ? C31 C30 C29 118.7(2) . . ? C31 C30 H30 120.7 . . ? C29 C30 H30 120.7 . . ? F1 C31 C32 118.3(2) . . ? F1 C31 C30 118.5(2) . . ? C32 C31 C30 123.21(19) . . ? C31 C32 C33 117.9(2) . . ? C31 C32 H32 121 . . ? C33 C32 H32 121 . . ? C28 C33 C32 120.86(17) . . ? C28 C33 H33 119.6 . . ? C32 C33 H33 119.6 . . ? C35 C34 C39 118.67(15) . . ? C35 C34 C16 121.07(15) . . ? C39 C34 C16 120.25(14) . . ? C36 C35 C34 120.72(18) . . ? C36 C35 H35 119.6 . . ? C34 C35 H35 119.6 . . ? C37 C36 C35 118.46(19) . . ? C37 C36 H36 120.8 . . ? C35 C36 H36 120.8 . . ? F2 C37 C38 118.3(2) . . ? F2 C37 C36 118.8(2) . . ? C38 C37 C36 122.96(17) . . ? C37 C38 C39 118.38(19) . . ? C37 C38 H38 120.8 . . ? C39 C38 H38 120.8 . . ? C38 C39 C34 120.80(18) . . ? C38 C39 H39 119.6 . . ? C34 C39 H39 119.6 . . ? O1 C40 H40A 109.5 . . ? O1 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? O1 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? O2 C41 H41A 109.5 . . ? O2 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? O2 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C7 N1 C3 115.85(14) . . ? C9 N2 C10 125.64(14) . . ? C9 N2 H200 119.6(15) . . ? C10 N2 H200 114.6(15) . . ? C12 N3 C11 125.17(14) . . ? C12 N3 H300 117.0(14) . . ? C11 N3 H300 117.7(14) . . ? C16 N4 C17 125.31(13) . . ? C16 N4 H400 120.6(14) . . ? C17 N4 H400 113.7(14) . . ? C19 N5 C18 124.27(12) . . ? C19 N5 H500 118.1(13) . . ? C18 N5 H500 117.5(13) . . ? C21 N6 C23 116.45(13) . . ? C40 O1 H1 109.5 . . ? C41 O2 H2A 109.5 . . ? F3' B1 F4 134.2(5) . . ? F3' B1 F4' 113.1(5) . . ? F3' B1 F5 107.9(4) . . ? F4 B1 F5 117.2(3) . . ? F4' B1 F5 139.0(5) . . ? F3' B1 F5' 121.1(5) . . ? F4 B1 F5' 97.4(4) . . ? F4' B1 F5' 110.3(7) . . ? F4 B1 F3 117.2(4) . . ? F4' B1 F3 102.2(6) . . ? F5 B1 F3 112.9(3) . . ? F5' B1 F3 145.4(4) . . ? F3' B1 F6 73.3(4) . . ? F4 B1 F6 101.5(4) . . ? F4' B1 F6 88.8(6) . . ? F5 B1 F6 104.5(3) . . ? F5' B1 F6 69.7(4) . . ? F3 B1 F6 100.1(3) . . ? F3' B1 F6' 109.8(4) . . ? F4 B1 F6' 83.8(4) . . ? F4' B1 F6' 99.1(6) . . ? F5 B1 F6' 64.7(3) . . ? F5' B1 F6' 100.4(4) . . ? F3 B1 F6' 85.6(3) . . ? F6 B1 F6' 169.2(3) . . ? #===END data_18b _database_code_depnum_ccdc_archive 'CCDC 805392' #TrackingRef 'CIF.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C34 H34 B Cl F6 N4 O0.50' _chemical_formula_sum 'C34 H34 B Cl F6 N4 O0.50' _chemical_formula_weight 666.91 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.3524(3) _cell_length_b 11.5299(2) _cell_length_c 18.2276(3) _cell_angle_alpha 90 _cell_angle_beta 112.4820(10) _cell_angle_gamma 90 _cell_volume 3369.66(10) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 9981 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 26.36 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1384 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.178 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker-AXS)' _exptl_absorpt_correction_T_min 0.9068 _exptl_absorpt_correction_T_max 0.9568 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_unetI/netI 0.0248 _diffrn_reflns_number 49681 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 27.13 _diffrn_reflns_theta_full 27.13 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _reflns_number_total 7401 _reflns_number_gt 5350 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1076P)^2^+2.8065P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 7401 _refine_ls_number_parameters 471 _refine_ls_number_restraints 168 _refine_ls_R_factor_all 0.0914 _refine_ls_R_factor_gt 0.0683 _refine_ls_wR_factor_ref 0.2135 _refine_ls_wR_factor_gt 0.1917 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.021 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.825 _refine_diff_density_min -0.826 _refine_diff_density_rms 0.06 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.08980(17) 0.3716(3) 0.30980(16) 0.0440(7) Uani 1 1 d . . . C2 C 0.13140(17) 0.3199(3) 0.38426(16) 0.0422(6) Uani 1 1 d . . . H2 H 0.111 0.2501 0.398 0.051 Uiso 1 1 calc R . . C3 C 0.20205(16) 0.3720(2) 0.43686(15) 0.0379(6) Uani 1 1 d . . . H3 H 0.2306 0.3373 0.4873 0.045 Uiso 1 1 calc R . . C4 C 0.23344(16) 0.4759(2) 0.41790(14) 0.0343(5) Uani 1 1 d . . . C5 C 0.18592(17) 0.5320(2) 0.34472(15) 0.0399(6) Uani 1 1 d . . . C6 C 0.11447(18) 0.4748(3) 0.29018(16) 0.0462(7) Uani 1 1 d . . . H6 H 0.0839 0.5088 0.2399 0.055 Uiso 1 1 calc R . . C7 C 0.2709(2) 0.6901(3) 0.37665(18) 0.0485(7) Uani 1 1 d . . . H7 H 0.2838 0.7659 0.3643 0.058 Uiso 1 1 calc R . . C8 C 0.32469(18) 0.6415(3) 0.44926(16) 0.0421(6) Uani 1 1 d . . . H8 H 0.3721 0.6833 0.4832 0.051 Uiso 1 1 calc R . . C9 C 0.30755(16) 0.5326(2) 0.47030(14) 0.0351(5) Uani 1 1 d . . . C10 C 0.39837(17) 0.3703(2) 0.53543(16) 0.0419(6) Uani 1 1 d . . . H10A H 0.445 0.3883 0.5187 0.05 Uiso 1 1 calc R . . H10B H 0.3583 0.3201 0.4944 0.05 Uiso 1 1 calc R . . C11 C 0.43143(18) 0.3069(2) 0.61430(17) 0.0464(7) Uani 1 1 d . . . H11A H 0.3843 0.2839 0.6291 0.056 Uiso 1 1 calc R . . H11B H 0.4609 0.2356 0.6094 0.056 Uiso 1 1 calc R . . C12 C 0.41668(16) 0.5534(2) 0.60235(15) 0.0367(6) Uani 1 1 d . . . H12A H 0.3895 0.6271 0.6068 0.044 Uiso 1 1 calc R . . H12B H 0.4635 0.572 0.586 0.044 Uiso 1 1 calc R . . C13 C 0.44976(16) 0.4929(2) 0.68200(15) 0.0380(6) Uani 1 1 d . . . H13A H 0.4913 0.5431 0.7217 0.046 Uiso 1 1 calc R . . H13B H 0.4034 0.4787 0.6999 0.046 Uiso 1 1 calc R . . C14 C 0.56465(15) 0.3486(2) 0.72588(14) 0.0315(5) Uani 1 1 d . . . C15 C 0.61731(16) 0.4349(2) 0.78513(15) 0.0357(5) Uani 1 1 d . . . C16 C 0.6232(2) 0.4328(3) 0.86329(17) 0.0527(7) Uani 1 1 d . . . H16 H 0.5892 0.3814 0.8785 0.063 Uiso 1 1 calc R . . C17 C 0.6790(3) 0.5061(3) 0.9193(2) 0.0675(10) Uani 1 1 d . . . H17 H 0.6838 0.5053 0.9729 0.081 Uiso 1 1 calc R . . C18 C 0.7267(2) 0.5790(3) 0.8953(2) 0.0667(10) Uani 1 1 d . . . C19 C 0.7209(2) 0.5854(3) 0.8187(3) 0.0669(10) Uani 1 1 d . . . H19 H 0.7538 0.639 0.8038 0.08 Uiso 1 1 calc R . . C20 C 0.66585(19) 0.5120(3) 0.7631(2) 0.0504(7) Uani 1 1 d . . . H20 H 0.6613 0.5144 0.7095 0.06 Uiso 1 1 calc R . . C21 C 0.59891(15) 0.2394(2) 0.72304(15) 0.0329(5) Uani 1 1 d . . . H21 H 0.5662 0.1833 0.6861 0.04 Uiso 1 1 calc R . . C22 C 0.67942(15) 0.2121(2) 0.77313(14) 0.0309(5) Uani 1 1 d . . . H22 H 0.7086 0.2671 0.8128 0.037 Uiso 1 1 calc R . . C23 C 0.72111(15) 0.1103(2) 0.77000(14) 0.0324(5) Uani 1 1 d . . . H23 H 0.6924 0.0524 0.7324 0.039 Uiso 1 1 calc R . . C24 C 0.80397(15) 0.0907(2) 0.82061(14) 0.0317(5) Uani 1 1 d . . . C25 C 0.84459(14) 0.1764(2) 0.88560(14) 0.0313(5) Uani 1 1 d . . . C26 C 0.83246(18) 0.1695(3) 0.95629(16) 0.0454(7) Uani 1 1 d . . . H26 H 0.8031 0.1053 0.9656 0.054 Uiso 1 1 calc R . . C27 C 0.8626(2) 0.2550(3) 1.01366(17) 0.0544(8) Uani 1 1 d . . . H27 H 0.8543 0.2501 1.0621 0.065 Uiso 1 1 calc R . . C28 C 0.90462(19) 0.3464(3) 0.99887(17) 0.0498(7) Uani 1 1 d . . . C29 C 0.9187(2) 0.3557(3) 0.93032(18) 0.0536(8) Uani 1 1 d . . . H29 H 0.9492 0.4194 0.9222 0.064 Uiso 1 1 calc R . . C30 C 0.88757(19) 0.2707(3) 0.87268(16) 0.0465(7) Uani 1 1 d . . . H30 H 0.8957 0.2769 0.8242 0.056 Uiso 1 1 calc R . . C31 C 0.81240(18) -0.0840(2) 0.74733(18) 0.0481(7) Uani 1 1 d . . . H31A H 0.7532 -0.0987 0.7382 0.058 Uiso 1 1 calc R . . H31B H 0.8429 -0.1584 0.7621 0.058 Uiso 1 1 calc R . . C32 C 0.93265(16) -0.0275(3) 0.87022(18) 0.0454(7) Uani 1 1 d . . . H32A H 0.9599 0.0445 0.8975 0.055 Uiso 1 1 calc R . . H32B H 0.9661 -0.059 0.8413 0.055 Uiso 1 1 calc R . . C33 C 0.9302(2) -0.1150(3) 0.9311(2) 0.0663(10) Uani 1 1 d . . . H33A H 0.9008 -0.0816 0.9625 0.1 Uiso 1 1 calc R . . H33B H 0.9873 -0.1351 0.9663 0.1 Uiso 1 1 calc R . . H33C H 0.9011 -0.185 0.904 0.1 Uiso 1 1 calc R . . N1 N 0.20455(16) 0.6397(2) 0.32470(14) 0.0492(6) Uani 1 1 d . . . N2 N 0.35649(13) 0.47931(18) 0.54246(12) 0.0350(5) Uani 1 1 d . . . N3 N 0.48888(13) 0.38177(18) 0.67632(13) 0.0370(5) Uani 1 1 d . . . N4 N 0.84787(13) -0.00060(19) 0.81332(13) 0.0375(5) Uani 1 1 d . . . F1 F 0.78183(17) 0.6495(2) 0.95070(17) 0.1075(10) Uani 1 1 d . . . F2 F 0.93378(16) 0.4314(2) 1.05487(12) 0.0787(7) Uani 1 1 d . . . Cl1 Cl 0.00244(5) 0.30060(9) 0.24209(5) 0.0639(3) Uani 1 1 d . . . C34 C 0.8180(2) -0.0391(3) 0.6716(2) 0.0644(9) Uani 1 1 d . . . H34A H 0.7881 0.0348 0.657 0.097 Uiso 1 1 calc R . . H34B H 0.7929 -0.0955 0.6289 0.097 Uiso 1 1 calc R . . H34C H 0.8767 -0.0274 0.6798 0.097 Uiso 1 1 calc R . . B1 B 0.4170(5) 0.2003(8) 0.3631(5) 0.0898(7) Uani 0.68 1 d PDU A 1 F3 F 0.4477(2) 0.2492(4) 0.3071(2) 0.0934(8) Uani 0.68 1 d PDU A 1 F4 F 0.4800(4) 0.2154(6) 0.4373(3) 0.0874(9) Uani 0.68 1 d PDU A 1 F5 F 0.3415(3) 0.2506(4) 0.3562(3) 0.0868(8) Uani 0.68 1 d PDU A 1 F6 F 0.4064(2) 0.0855(3) 0.3465(2) 0.0935(8) Uani 0.68 1 d PDU A 1 B1' B 0.4081(10) 0.1916(14) 0.3696(9) 0.0902(7) Uani 0.32 1 d PDU B 2 F3' F 0.3949(5) 0.1645(8) 0.2930(5) 0.0922(9) Uani 0.32 1 d PDU B 2 F4' F 0.4844(8) 0.2267(14) 0.4179(6) 0.0889(11) Uani 0.32 1 d PDU B 2 F5' F 0.3552(7) 0.2872(8) 0.3600(7) 0.0882(10) Uani 0.32 1 d PDU B 2 F6' F 0.3800(5) 0.1135(8) 0.4093(5) 0.0969(10) Uani 0.32 1 d PDU B 2 O1 O 0.5911(5) 0.0934(7) 0.5540(5) 0.114(2) Uani 0.5 1 d PU . . 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 0.0343(13) 0.0590(18) 0.0358(14) -0.0050(12) 0.0102(11) 0.0104(12) C2 0.0406(14) 0.0439(15) 0.0400(14) 0.0006(12) 0.0132(12) 0.0060(12) C3 0.0398(13) 0.0403(14) 0.0308(12) 0.0058(10) 0.0104(11) 0.0111(11) C4 0.0361(13) 0.0398(13) 0.0293(12) 0.0033(10) 0.0152(10) 0.0115(10) C5 0.0420(14) 0.0484(15) 0.0322(13) 0.0086(11) 0.0174(11) 0.0138(12) C6 0.0427(15) 0.0642(19) 0.0290(13) 0.0082(12) 0.0104(11) 0.0175(14) C7 0.0601(18) 0.0467(16) 0.0455(16) 0.0143(13) 0.0278(15) 0.0087(14) C8 0.0457(15) 0.0450(15) 0.0391(14) 0.0062(12) 0.0200(12) 0.0042(12) C9 0.0398(13) 0.0393(13) 0.0302(12) 0.0042(10) 0.0179(11) 0.0099(11) C10 0.0393(14) 0.0392(14) 0.0395(14) -0.0080(11) 0.0063(11) 0.0090(11) C11 0.0388(14) 0.0323(14) 0.0493(16) -0.0034(12) -0.0042(12) 0.0045(11) C12 0.0398(13) 0.0332(13) 0.0364(13) -0.0022(10) 0.0140(11) 0.0053(10) C13 0.0365(13) 0.0376(14) 0.0351(13) -0.0029(10) 0.0084(11) 0.0097(11) C14 0.0319(12) 0.0322(12) 0.0282(11) 0.0039(9) 0.0088(9) 0.0020(10) C15 0.0337(12) 0.0322(12) 0.0351(12) -0.0007(10) 0.0065(10) 0.0057(10) C16 0.065(2) 0.0490(17) 0.0369(15) -0.0039(13) 0.0116(14) 0.0007(15) C17 0.085(3) 0.060(2) 0.0393(17) -0.0118(15) 0.0031(17) 0.0088(19) C18 0.057(2) 0.0447(18) 0.071(2) -0.0285(17) -0.0054(17) 0.0019(15) C19 0.060(2) 0.0486(19) 0.089(3) -0.0202(18) 0.0239(19) -0.0151(16) C20 0.0503(17) 0.0457(16) 0.0549(18) -0.0106(14) 0.0199(14) -0.0088(13) C21 0.0303(12) 0.0307(12) 0.0343(12) 0.0001(10) 0.0086(10) -0.0015(9) C22 0.0311(12) 0.0315(12) 0.0288(11) 0.0027(9) 0.0100(9) -0.0024(9) C23 0.0293(12) 0.0307(12) 0.0335(12) 0.0020(10) 0.0078(10) -0.0019(9) C24 0.0303(12) 0.0306(12) 0.0335(12) 0.0053(9) 0.0115(10) -0.0005(9) C25 0.0262(11) 0.0350(12) 0.0287(11) 0.0053(9) 0.0062(9) 0.0018(9) C26 0.0414(15) 0.0587(18) 0.0376(14) 0.0025(13) 0.0169(12) -0.0102(13) C27 0.0529(18) 0.078(2) 0.0349(14) -0.0065(14) 0.0201(13) -0.0115(16) C28 0.0525(17) 0.0517(17) 0.0371(14) -0.0087(13) 0.0080(13) -0.0066(14) C29 0.068(2) 0.0460(17) 0.0426(15) -0.0018(13) 0.0166(14) -0.0221(15) C30 0.0588(18) 0.0470(16) 0.0346(13) 0.0001(12) 0.0190(13) -0.0154(13) C31 0.0427(15) 0.0342(14) 0.0559(17) -0.0079(12) 0.0061(13) 0.0085(12) C32 0.0280(12) 0.0464(16) 0.0551(17) 0.0023(13) 0.0084(12) 0.0061(11) C33 0.0508(19) 0.063(2) 0.069(2) 0.0253(18) 0.0049(16) 0.0129(16) N1 0.0562(15) 0.0553(15) 0.0372(12) 0.0169(11) 0.0191(11) 0.0134(12) N2 0.0379(11) 0.0331(11) 0.0311(10) 0.0011(8) 0.0099(9) 0.0083(9) N3 0.0329(11) 0.0327(11) 0.0367(11) -0.0017(9) 0.0035(9) 0.0046(9) N4 0.0305(10) 0.0359(11) 0.0407(12) 0.0021(9) 0.0077(9) 0.0039(9) F1 0.0958(18) 0.0778(16) 0.105(2) -0.0548(15) -0.0104(15) -0.0141(14) F2 0.1005(17) 0.0772(14) 0.0533(11) -0.0295(10) 0.0237(11) -0.0270(13) Cl1 0.0457(4) 0.0843(6) 0.0469(4) -0.0085(4) 0.0012(3) 0.0009(4) C34 0.076(2) 0.062(2) 0.0492(18) -0.0118(16) 0.0172(17) 0.0115(18) B1 0.0840(12) 0.0912(14) 0.0901(13) -0.0303(12) 0.0287(11) -0.0136(11) F3 0.0891(14) 0.0979(16) 0.0928(15) -0.0232(14) 0.0345(13) -0.0102(13) F4 0.0806(14) 0.0894(16) 0.0878(17) -0.0326(15) 0.0271(14) -0.0148(12) F5 0.0807(15) 0.0904(17) 0.0857(14) -0.0322(15) 0.0277(13) -0.0124(14) F6 0.0870(14) 0.0883(15) 0.0956(15) -0.0333(13) 0.0241(12) -0.0177(12) B1' 0.0843(12) 0.0914(14) 0.0905(13) -0.0302(12) 0.0284(11) -0.0137(11) F3' 0.0876(15) 0.0936(17) 0.0918(16) -0.0307(14) 0.0302(14) -0.0123(14) F4' 0.0811(15) 0.0902(17) 0.0909(18) -0.0318(17) 0.0277(16) -0.0164(14) F5' 0.0835(16) 0.0910(18) 0.0868(16) -0.0296(17) 0.0289(15) -0.0104(15) F6' 0.0885(16) 0.0948(17) 0.0973(17) -0.0243(16) 0.0241(15) -0.0183(15) O1 0.116(2) 0.113(2) 0.112(2) 0.0007(10) 0.0418(13) -0.0029(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.358(5) . ? C1 C2 1.403(4) . ? C1 Cl1 1.749(3) . ? C2 C3 1.372(4) . ? C2 H2 0.95 . ? C3 C4 1.413(4) . ? C3 H3 0.95 . ? C4 C5 1.427(3) . ? C4 C9 1.433(4) . ? C5 N1 1.367(4) . ? C5 C6 1.420(4) . ? C6 H6 0.95 . ? C7 N1 1.314(4) . ? C7 C8 1.411(4) . ? C7 H7 0.95 . ? C8 C9 1.378(4) . ? C8 H8 0.95 . ? C9 N2 1.405(3) . ? C10 N2 1.481(3) . ? C10 C11 1.517(4) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 N3 1.468(3) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 N2 1.463(3) . ? C12 C13 1.513(4) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C13 N3 1.472(3) . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 N3 1.335(3) . ? C14 C21 1.401(3) . ? C14 C15 1.496(3) . ? C15 C20 1.385(4) . ? C15 C16 1.389(4) . ? C16 C17 1.392(5) . ? C16 H16 0.95 . ? C17 C18 1.363(6) . ? C17 H17 0.95 . ? C18 F1 1.362(4) . ? C18 C19 1.363(6) . ? C19 C20 1.384(4) . ? C19 H19 0.95 . ? C20 H20 0.95 . ? C21 C22 1.382(3) . ? C21 H21 0.95 . ? C22 C23 1.391(3) . ? C22 H22 0.95 . ? C23 C24 1.398(3) . ? C23 H23 0.95 . ? C24 N4 1.335(3) . ? C24 C25 1.496(3) . ? C25 C26 1.385(4) . ? C25 C30 1.388(4) . ? C26 C27 1.386(4) . ? C26 H26 0.95 . ? C27 C28 1.366(5) . ? C27 H27 0.95 . ? C28 F2 1.365(3) . ? C28 C29 1.366(4) . ? C29 C30 1.387(4) . ? C29 H29 0.95 . ? C30 H30 0.95 . ? C31 N4 1.478(4) . ? C31 C34 1.512(5) . ? C31 H31A 0.99 . ? C31 H31B 0.99 . ? C32 N4 1.473(3) . ? C32 C33 1.512(5) . ? C32 H32A 0.99 . ? C32 H32B 0.99 . ? C33 H33A 0.98 . ? C33 H33B 0.98 . ? C33 H33C 0.98 . ? C34 H34A 0.98 . ? C34 H34B 0.98 . ? C34 H34C 0.98 . ? B1 F6 1.355(10) . ? B1 F4 1.387(9) . ? B1 F5 1.395(9) . ? B1 F3 1.434(9) . ? B1' F4' 1.342(15) . ? B1' F6' 1.357(15) . ? B1' F3' 1.362(15) . ? B1' F5' 1.402(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 122.0(3) . . ? C6 C1 Cl1 120.0(2) . . ? C2 C1 Cl1 118.0(2) . . ? C3 C2 C1 118.8(3) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 121.7(2) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C3 C4 C5 118.3(2) . . ? C3 C4 C9 123.8(2) . . ? C5 C4 C9 117.8(2) . . ? N1 C5 C6 117.8(2) . . ? N1 C5 C4 123.4(3) . . ? C6 C5 C4 118.8(3) . . ? C1 C6 C5 120.1(2) . . ? C1 C6 H6 120 . . ? C5 C6 H6 120 . . ? N1 C7 C8 125.6(3) . . ? N1 C7 H7 117.2 . . ? C8 C7 H7 117.2 . . ? C9 C8 C7 119.1(3) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C8 C9 N2 122.8(2) . . ? C8 C9 C4 117.7(2) . . ? N2 C9 C4 119.4(2) . . ? N2 C10 C11 110.3(2) . . ? N2 C10 H10A 109.6 . . ? C11 C10 H10A 109.6 . . ? N2 C10 H10B 109.6 . . ? C11 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? N3 C11 C10 110.2(2) . . ? N3 C11 H11A 109.6 . . ? C10 C11 H11A 109.6 . . ? N3 C11 H11B 109.6 . . ? C10 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? N2 C12 C13 110.3(2) . . ? N2 C12 H12A 109.6 . . ? C13 C12 H12A 109.6 . . ? N2 C12 H12B 109.6 . . ? C13 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? N3 C13 C12 110.5(2) . . ? N3 C13 H13A 109.5 . . ? C12 C13 H13A 109.5 . . ? N3 C13 H13B 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? N3 C14 C21 123.7(2) . . ? N3 C14 C15 118.0(2) . . ? C21 C14 C15 118.3(2) . . ? C20 C15 C16 119.6(3) . . ? C20 C15 C14 119.3(2) . . ? C16 C15 C14 120.9(3) . . ? C15 C16 C17 119.9(3) . . ? C15 C16 H16 120 . . ? C17 C16 H16 120 . . ? C18 C17 C16 118.5(3) . . ? C18 C17 H17 120.7 . . ? C16 C17 H17 120.7 . . ? F1 C18 C17 118.1(4) . . ? F1 C18 C19 118.9(4) . . ? C17 C18 C19 123.0(3) . . ? C18 C19 C20 118.5(3) . . ? C18 C19 H19 120.7 . . ? C20 C19 H19 120.7 . . ? C19 C20 C15 120.4(3) . . ? C19 C20 H20 119.8 . . ? C15 C20 H20 119.8 . . ? C22 C21 C14 121.1(2) . . ? C22 C21 H21 119.4 . . ? C14 C21 H21 119.4 . . ? C21 C22 C23 125.2(2) . . ? C21 C22 H22 117.4 . . ? C23 C22 H22 117.4 . . ? C22 C23 C24 121.9(2) . . ? C22 C23 H23 119 . . ? C24 C23 H23 119 . . ? N4 C24 C23 122.9(2) . . ? N4 C24 C25 119.0(2) . . ? C23 C24 C25 118.0(2) . . ? C26 C25 C30 119.1(2) . . ? C26 C25 C24 120.3(2) . . ? C30 C25 C24 120.3(2) . . ? C25 C26 C27 120.9(3) . . ? C25 C26 H26 119.6 . . ? C27 C26 H26 119.6 . . ? C28 C27 C26 118.4(3) . . ? C28 C27 H27 120.8 . . ? C26 C27 H27 120.8 . . ? F2 C28 C29 118.9(3) . . ? F2 C28 C27 118.7(3) . . ? C29 C28 C27 122.5(3) . . ? C28 C29 C30 118.9(3) . . ? C28 C29 H29 120.5 . . ? C30 C29 H29 120.5 . . ? C29 C30 C25 120.2(3) . . ? C29 C30 H30 119.9 . . ? C25 C30 H30 119.9 . . ? N4 C31 C34 111.6(3) . . ? N4 C31 H31A 109.3 . . ? C34 C31 H31A 109.3 . . ? N4 C31 H31B 109.3 . . ? C34 C31 H31B 109.3 . . ? H31A C31 H31B 108 . . ? N4 C32 C33 110.9(2) . . ? N4 C32 H32A 109.5 . . ? C33 C32 H32A 109.5 . . ? N4 C32 H32B 109.5 . . ? C33 C32 H32B 109.5 . . ? H32A C32 H32B 108 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C7 N1 C5 116.2(2) . . ? C9 N2 C12 116.5(2) . . ? C9 N2 C10 115.5(2) . . ? C12 N2 C10 109.03(19) . . ? C14 N3 C11 123.7(2) . . ? C14 N3 C13 124.3(2) . . ? C11 N3 C13 111.7(2) . . ? C24 N4 C32 123.4(2) . . ? C24 N4 C31 121.2(2) . . ? C32 N4 C31 115.4(2) . . ? C31 C34 H34A 109.5 . . ? C31 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C31 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? F6 B1 F4 109.2(7) . . ? F6 B1 F5 110.1(7) . . ? F4 B1 F5 113.5(7) . . ? F6 B1 F3 106.4(6) . . ? F4 B1 F3 106.0(6) . . ? F5 B1 F3 111.4(7) . . ? F4' B1' F6' 108.4(13) . . ? F4' B1' F3' 118.6(13) . . ? F6' B1' F3' 116.1(13) . . ? F4' B1' F5' 106.2(14) . . ? F6' B1' F5' 103.7(12) . . ? F3' B1' F5' 101.9(12) . . ? #===END data_19b _database_code_depnum_ccdc_archive 'CCDC 805393' #TrackingRef 'CIF.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C34.50 H36 B Cl F6 N4 O2.50' _chemical_formula_sum 'C34.50 H36 B Cl F6 N4 O2.50' _chemical_formula_weight 706.93 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.3858(4) _cell_length_b 11.0501(2) _cell_length_c 30.9188(7) _cell_angle_alpha 90 _cell_angle_beta 108.7700(10) _cell_angle_gamma 90 _cell_volume 6918.0(2) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3934 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 21.98 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.24 _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2936 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.182 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker-AXS)' _exptl_absorpt_correction_T_min 0.9082 _exptl_absorpt_correction_T_max 0.9577 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'microfocus sealed tube' _diffrn_radiation_monochromator 'multilayer optics' _diffrn_measurement_device_type 'Bruker Kappa APEX II Quazar' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0723 _diffrn_reflns_av_unetI/netI 0.0719 _diffrn_reflns_number 30548 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 5.12 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _reflns_number_total 7013 _reflns_number_gt 4423 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0475P)^2^+10.2240P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 7013 _refine_ls_number_parameters 487 _refine_ls_number_restraints 38 _refine_ls_R_factor_all 0.1021 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1333 _refine_ls_wR_factor_gt 0.1132 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.458 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.054 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O2 O 0.43311(14) 0.4094(2) 0.63786(10) 0.0657(8) Uani 1 1 d D . . H100 H 0.3940(12) 0.452(3) 0.6377(14) 0.079 Uiso 1 1 d D . . H101 H 0.445(2) 0.348(3) 0.6608(10) 0.079 Uiso 1 1 d D . . C35 C 0.5069(19) 0.4275(8) 0.2439(11) 0.085(5) Uani 0.5 1 d P A -1 H35A H 0.5414 0.4034 0.2721 0.128 Uiso 0.5 1 calc PR A -1 H35B H 0.4731 0.3642 0.2349 0.128 Uiso 0.5 1 calc PR A -1 H35C H 0.4867 0.5034 0.2491 0.128 Uiso 0.5 1 calc PR A -1 O3 O 0.5351(3) 0.4440(6) 0.2089(2) 0.093(2) Uani 0.5 1 d P A -1 H3 H 0.5094 0.4853 0.1878 0.14 Uiso 0.5 1 calc PR A -1 C1 C 0.08399(16) 0.2362(3) 0.50718(10) 0.0335(7) Uani 1 1 d . . . H1A H 0.0464 0.1789 0.4985 0.04 Uiso 1 1 calc R . . H1B H 0.1249 0.1893 0.5215 0.04 Uiso 1 1 calc R . . C2 C 0.08877(14) 0.2994(2) 0.46435(9) 0.0261(6) Uani 1 1 d . . . H2A H 0.0978 0.239 0.4435 0.031 Uiso 1 1 calc R . . H2B H 0.0463 0.3397 0.4481 0.031 Uiso 1 1 calc R . . C3 C 0.12937(15) 0.4042(3) 0.55318(9) 0.0321(7) Uani 1 1 d . . . H3A H 0.1707 0.3583 0.5673 0.039 Uiso 1 1 calc R . . H3B H 0.1233 0.4606 0.5764 0.039 Uiso 1 1 calc R . . C4 C 0.13534(14) 0.4760(2) 0.51271(9) 0.0249(6) Uani 1 1 d . . . H4A H 0.0955 0.5266 0.4997 0.03 Uiso 1 1 calc R . . H4B H 0.1742 0.5301 0.5228 0.03 Uiso 1 1 calc R . . C5 C 0.18721(13) 0.4042(2) 0.45596(8) 0.0213(6) Uani 1 1 d . . . C6 C 0.24135(13) 0.4948(2) 0.47543(8) 0.0226(6) Uani 1 1 d . . . C7 C 0.29096(14) 0.4698(3) 0.51682(9) 0.0280(6) Uani 1 1 d . . . H7 H 0.288 0.3995 0.5337 0.034 Uiso 1 1 calc R . . C8 C 0.34450(15) 0.5478(3) 0.53318(10) 0.0373(8) Uani 1 1 d . . . H8 H 0.3785 0.5316 0.5611 0.045 Uiso 1 1 calc R . . C9 C 0.34686(16) 0.6497(3) 0.50773(11) 0.0398(8) Uani 1 1 d . . . C10 C 0.29859(16) 0.6793(3) 0.46717(10) 0.0374(8) Uani 1 1 d . . . H10 H 0.3017 0.7508 0.4509 0.045 Uiso 1 1 calc R . . C11 C 0.24535(15) 0.6005(3) 0.45100(9) 0.0292(7) Uani 1 1 d . . . H11 H 0.2114 0.6183 0.4232 0.035 Uiso 1 1 calc R . . C12 C 0.18682(13) 0.3355(2) 0.41727(8) 0.0205(6) Uani 1 1 d . . . H12 H 0.1527 0.278 0.405 0.025 Uiso 1 1 calc R . . C13 C 0.23535(13) 0.3505(2) 0.39680(8) 0.0203(6) Uani 1 1 d . . . H13 H 0.269 0.4083 0.4099 0.024 Uiso 1 1 calc R . . C14 C 0.23839(13) 0.2868(2) 0.35833(8) 0.0213(6) Uani 1 1 d . . . H14 H 0.2059 0.2273 0.345 0.026 Uiso 1 1 calc R . . C15 C 0.28830(13) 0.3092(2) 0.33921(8) 0.0204(6) Uani 1 1 d . . . C16 C 0.33263(13) 0.4168(2) 0.35550(8) 0.0224(6) Uani 1 1 d . . . C17 C 0.30708(14) 0.5346(2) 0.34567(9) 0.0277(6) Uani 1 1 d . . . H17 H 0.2619 0.5453 0.3282 0.033 Uiso 1 1 calc R . . C18 C 0.34693(17) 0.6361(3) 0.36116(10) 0.0374(8) Uani 1 1 d . . . H18 H 0.3298 0.7158 0.3546 0.045 Uiso 1 1 calc R . . C19 C 0.41201(17) 0.6161(3) 0.38633(11) 0.0435(9) Uani 1 1 d . . . C20 C 0.43892(16) 0.5023(3) 0.39720(11) 0.0432(8) Uani 1 1 d . . . H20 H 0.4839 0.4928 0.4152 0.052 Uiso 1 1 calc R . . C21 C 0.39899(14) 0.4011(3) 0.38139(9) 0.0307(7) Uani 1 1 d . . . H21 H 0.4168 0.322 0.3882 0.037 Uiso 1 1 calc R . . C22 C 0.26014(14) 0.1286(3) 0.28788(10) 0.0294(7) Uani 1 1 d . . . H22A H 0.2295 0.1448 0.2568 0.035 Uiso 1 1 calc R . . H22B H 0.2334 0.1062 0.3075 0.035 Uiso 1 1 calc R . . C23 C 0.30518(14) 0.0230(3) 0.28591(9) 0.0274(6) Uani 1 1 d . . . H23A H 0.3333 0.0012 0.3172 0.033 Uiso 1 1 calc R . . H23B H 0.2782 -0.0484 0.2721 0.033 Uiso 1 1 calc R . . C24 C 0.34311(13) 0.2718(2) 0.28023(9) 0.0246(6) Uani 1 1 d . . . H24A H 0.3705 0.3422 0.2947 0.029 Uiso 1 1 calc R . . H24B H 0.3171 0.2941 0.2485 0.029 Uiso 1 1 calc R . . C25 C 0.38727(13) 0.1646(2) 0.27978(9) 0.0248(6) Uani 1 1 d . . . H25A H 0.4174 0.1858 0.2624 0.03 Uiso 1 1 calc R . . H25B H 0.4145 0.1445 0.3115 0.03 Uiso 1 1 calc R . . C26 C 0.37669(12) -0.0361(2) 0.24159(9) 0.0234(6) Uani 1 1 d . . . C29 C 0.43538(12) -0.1057(3) 0.18982(8) 0.0231(6) Uani 1 1 d . . . C30 C 0.40311(13) -0.0096(2) 0.20514(8) 0.0226(6) Uani 1 1 d . . . C31 C 0.39592(13) 0.1044(3) 0.18227(9) 0.0258(6) Uani 1 1 d . . . H31 H 0.3706 0.1663 0.19 0.031 Uiso 1 1 calc R . . C32 C 0.42486(14) 0.1261(3) 0.14922(9) 0.0276(6) Uani 1 1 d . . . H32 H 0.4201 0.2025 0.1344 0.033 Uiso 1 1 calc R . . C33 C 0.46172(13) 0.0328(3) 0.13781(9) 0.0251(6) Uani 1 1 d . . . C34 C 0.46614(13) -0.0812(3) 0.15624(9) 0.0269(6) Uani 1 1 d . . . H34 H 0.4895 -0.1431 0.1466 0.032 Uiso 1 1 calc R . . N1 N 0.14259(11) 0.3903(2) 0.47750(7) 0.0236(5) Uani 1 1 d . . . N2 N 0.29807(11) 0.2398(2) 0.30602(7) 0.0241(5) Uani 1 1 d . . . N3 N 0.34678(11) 0.05811(19) 0.25848(7) 0.0226(5) Uani 1 1 d . . . F1 F 0.39993(10) 0.72602(19) 0.52376(7) 0.0637(6) Uani 1 1 d . . . F2 F 0.45100(11) 0.71613(19) 0.40185(8) 0.0687(7) Uani 1 1 d . . . Cl1 Cl 0.50064(4) 0.06744(7) 0.09761(2) 0.0327(2) Uani 1 1 d . . . O1 O 0.07491(11) 0.32202(18) 0.53939(7) 0.0379(5) Uani 1 1 d . . . F3 F 0.31715(11) 0.32328(18) 0.11575(7) 0.0572(6) Uani 1 1 d . B . B1 B 0.2872(2) 0.3954(3) 0.13891(13) 0.0391(9) Uani 1 1 d D . . F4 F 0.2700(2) 0.3152(4) 0.17026(15) 0.0509(12) Uani 0.54 1 d PDU B 1 F5 F 0.2346(3) 0.4552(5) 0.1147(2) 0.0736(18) Uani 0.54 1 d PDU B 1 F6 F 0.3334(2) 0.4730(5) 0.1715(2) 0.0813(14) Uani 0.54 1 d PDU B 1 F4' F 0.2996(4) 0.3729(8) 0.1811(2) 0.089(2) Uani 0.46 1 d PDU B 2 F5' F 0.2192(3) 0.3971(5) 0.1142(3) 0.0671(19) Uani 0.46 1 d PDU B 2 F6' F 0.3059(3) 0.5171(4) 0.1308(2) 0.0609(12) Uani 0.46 1 d PDU B 2 N4 N 0.43686(11) -0.2239(2) 0.20487(8) 0.0282(5) Uani 1 1 d . . . C27 C 0.37946(13) -0.1559(3) 0.25616(9) 0.0270(6) Uani 1 1 d . . . H27 H 0.3616 -0.1773 0.2795 0.032 Uiso 1 1 calc R . . C28 C 0.40862(14) -0.2455(3) 0.23645(9) 0.0286(6) Uani 1 1 d . . . H28 H 0.408 -0.3266 0.2464 0.034 Uiso 1 1 calc 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 O2 0.076(2) 0.0525(17) 0.086(2) 0.0255(15) 0.0500(17) 0.0107(15) C35 0.109(14) 0.070(5) 0.088(17) 0.011(7) 0.048(8) 0.019(8) O3 0.105(5) 0.103(5) 0.091(5) 0.029(4) 0.059(4) 0.062(4) C1 0.0491(19) 0.0264(16) 0.0355(17) -0.0044(13) 0.0282(15) -0.0060(14) C2 0.0302(15) 0.0275(15) 0.0247(14) -0.0035(12) 0.0146(12) -0.0053(12) C3 0.0421(17) 0.0380(18) 0.0229(15) -0.0034(13) 0.0197(13) -0.0012(14) C4 0.0315(15) 0.0264(15) 0.0229(14) -0.0047(12) 0.0172(12) -0.0002(12) C5 0.0263(14) 0.0234(15) 0.0166(13) 0.0026(11) 0.0103(11) -0.0001(12) C6 0.0304(15) 0.0266(15) 0.0163(13) -0.0044(11) 0.0150(12) -0.0021(12) C7 0.0342(16) 0.0315(17) 0.0209(14) -0.0031(12) 0.0124(12) -0.0002(13) C8 0.0330(17) 0.048(2) 0.0281(16) -0.0131(15) 0.0067(13) -0.0065(15) C9 0.0395(18) 0.0402(19) 0.0432(19) -0.0189(16) 0.0181(16) -0.0193(15) C10 0.053(2) 0.0310(17) 0.0329(17) -0.0070(14) 0.0209(16) -0.0143(15) C11 0.0413(17) 0.0275(16) 0.0224(14) -0.0042(12) 0.0154(13) -0.0060(13) C12 0.0256(14) 0.0229(14) 0.0156(13) -0.0015(11) 0.0102(11) -0.0030(11) C13 0.0238(14) 0.0239(15) 0.0137(12) 0.0020(11) 0.0069(11) -0.0007(11) C14 0.0249(14) 0.0254(15) 0.0149(13) -0.0023(11) 0.0082(11) -0.0026(12) C15 0.0256(14) 0.0230(14) 0.0135(12) 0.0004(11) 0.0074(11) 0.0012(11) C16 0.0275(14) 0.0292(16) 0.0152(13) -0.0015(11) 0.0135(11) -0.0036(12) C17 0.0363(16) 0.0293(16) 0.0224(14) -0.0018(12) 0.0165(13) -0.0048(13) C18 0.055(2) 0.0284(17) 0.0398(18) -0.0013(14) 0.0298(17) -0.0060(15) C19 0.053(2) 0.040(2) 0.046(2) -0.0163(16) 0.0272(17) -0.0266(17) C20 0.0319(17) 0.057(2) 0.0400(19) -0.0074(17) 0.0105(15) -0.0120(16) C21 0.0313(16) 0.0343(17) 0.0280(15) -0.0031(13) 0.0118(13) -0.0029(13) C22 0.0308(15) 0.0332(17) 0.0308(16) -0.0119(13) 0.0189(13) -0.0089(13) C23 0.0344(16) 0.0289(16) 0.0254(15) -0.0047(12) 0.0188(13) -0.0062(13) C24 0.0330(15) 0.0272(15) 0.0205(14) -0.0022(12) 0.0184(12) -0.0053(12) C25 0.0275(15) 0.0323(16) 0.0189(13) -0.0011(12) 0.0133(11) -0.0028(12) C26 0.0192(13) 0.0325(16) 0.0184(13) -0.0034(12) 0.0059(11) -0.0009(12) C29 0.0209(13) 0.0313(16) 0.0172(13) -0.0031(12) 0.0063(11) -0.0001(12) C30 0.0218(13) 0.0295(16) 0.0167(13) -0.0020(12) 0.0064(11) -0.0018(12) C31 0.0299(15) 0.0285(16) 0.0219(14) -0.0013(12) 0.0124(12) 0.0022(12) C32 0.0326(16) 0.0315(16) 0.0208(14) 0.0010(12) 0.0117(12) -0.0010(13) C33 0.0256(14) 0.0344(17) 0.0184(14) -0.0056(12) 0.0115(11) -0.0071(12) C34 0.0250(14) 0.0360(17) 0.0229(14) -0.0081(13) 0.0123(12) -0.0017(13) N1 0.0311(13) 0.0266(13) 0.0185(11) -0.0040(10) 0.0155(10) -0.0035(10) N2 0.0298(13) 0.0279(13) 0.0207(11) -0.0046(10) 0.0165(10) -0.0062(10) N3 0.0281(12) 0.0250(13) 0.0200(11) -0.0024(10) 0.0152(10) -0.0030(10) F1 0.0568(13) 0.0637(14) 0.0656(14) -0.0185(11) 0.0126(11) -0.0358(11) F2 0.0722(15) 0.0587(14) 0.0817(16) -0.0277(12) 0.0337(13) -0.0429(12) Cl1 0.0356(4) 0.0456(5) 0.0239(4) -0.0056(3) 0.0195(3) -0.0077(3) O1 0.0545(14) 0.0382(12) 0.0356(12) -0.0075(10) 0.0348(11) -0.0107(10) F3 0.0844(16) 0.0509(12) 0.0498(12) 0.0057(10) 0.0403(11) 0.0240(11) B1 0.050(2) 0.033(2) 0.040(2) -0.0025(18) 0.0227(19) 0.0096(19) F4 0.060(3) 0.061(3) 0.034(2) 0.013(2) 0.018(2) -0.005(2) F5 0.092(4) 0.072(4) 0.061(3) 0.034(3) 0.030(3) 0.052(3) F6 0.053(3) 0.075(3) 0.123(4) -0.051(3) 0.038(3) -0.015(2) F4' 0.125(6) 0.108(5) 0.040(3) 0.018(4) 0.034(4) 0.058(4) F5' 0.054(3) 0.043(4) 0.106(4) 0.015(4) 0.028(3) 0.018(3) F6' 0.076(3) 0.034(2) 0.088(3) -0.017(2) 0.048(3) -0.003(2) N4 0.0302(13) 0.0300(14) 0.0258(13) -0.0012(11) 0.0111(10) 0.0028(11) C27 0.0298(15) 0.0337(17) 0.0200(14) 0.0015(12) 0.0114(12) -0.0019(13) C28 0.0319(16) 0.0284(16) 0.0270(15) 0.0038(13) 0.0116(12) 0.0013(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 H100 0.96(3) . ? O2 H101 0.96(3) . ? C35 O3 1.412(19) . ? C35 H35A 0.98 . ? C35 H35B 0.98 . ? C35 H35C 0.98 . ? O3 H3 0.84 . ? C1 O1 1.433(3) . ? C1 C2 1.529(4) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C2 N1 1.482(3) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 O1 1.429(3) . ? C3 C4 1.522(4) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 N1 1.488(3) . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C5 N1 1.337(3) . ? C5 C12 1.415(3) . ? C5 C6 1.502(4) . ? C6 C7 1.402(4) . ? C6 C11 1.409(4) . ? C7 C8 1.392(4) . ? C7 H7 0.95 . ? C8 C9 1.384(4) . ? C8 H8 0.95 . ? C9 F1 1.372(3) . ? C9 C10 1.383(5) . ? C10 C11 1.392(4) . ? C10 H10 0.95 . ? C11 H11 0.95 . ? C12 C13 1.388(3) . ? C12 H12 0.95 . ? C13 C14 1.402(3) . ? C13 H13 0.95 . ? C14 C15 1.398(3) . ? C14 H14 0.95 . ? C15 N2 1.350(3) . ? C15 C16 1.503(4) . ? C16 C21 1.398(4) . ? C16 C17 1.406(4) . ? C17 C18 1.397(4) . ? C17 H17 0.95 . ? C18 C19 1.376(5) . ? C18 H18 0.95 . ? C19 F2 1.374(3) . ? C19 C20 1.379(5) . ? C20 C21 1.396(4) . ? C20 H20 0.95 . ? C21 H21 0.95 . ? C22 N2 1.480(3) . ? C22 C23 1.527(4) . ? C22 H22A 0.99 . ? C22 H22B 0.99 . ? C23 N3 1.465(3) . ? C23 H23A 0.99 . ? C23 H23B 0.99 . ? C24 N2 1.477(3) . ? C24 C25 1.518(4) . ? C24 H24A 0.99 . ? C24 H24B 0.99 . ? C25 N3 1.483(3) . ? C25 H25A 0.99 . ? C25 H25B 0.99 . ? C26 C27 1.393(4) . ? C26 N3 1.407(3) . ? C26 C30 1.444(3) . ? C29 N4 1.383(4) . ? C29 C34 1.423(3) . ? C29 C30 1.428(4) . ? C30 C31 1.428(4) . ? C31 C32 1.376(3) . ? C31 H31 0.95 . ? C32 C33 1.410(4) . ? C32 H32 0.95 . ? C33 C34 1.373(4) . ? C33 Cl1 1.746(2) . ? C34 H34 0.95 . ? F3 B1 1.361(4) . ? B1 F4' 1.269(6) . ? B1 F5 1.312(7) . ? B1 F5' 1.408(8) . ? B1 F6 1.444(6) . ? B1 F4 1.446(6) . ? B1 F6' 1.448(6) . ? N4 C28 1.325(3) . ? C27 C28 1.409(4) . ? C27 H27 0.95 . ? C28 H28 0.95 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag H100 O2 H101 112(4) . . ? O1 C1 C2 111.2(2) . . ? O1 C1 H1A 109.4 . . ? C2 C1 H1A 109.4 . . ? O1 C1 H1B 109.4 . . ? C2 C1 H1B 109.4 . . ? H1A C1 H1B 108 . . ? N1 C2 C1 109.5(2) . . ? N1 C2 H2A 109.8 . . ? C1 C2 H2A 109.8 . . ? N1 C2 H2B 109.8 . . ? C1 C2 H2B 109.8 . . ? H2A C2 H2B 108.2 . . ? O1 C3 C4 111.2(2) . . ? O1 C3 H3A 109.4 . . ? C4 C3 H3A 109.4 . . ? O1 C3 H3B 109.4 . . ? C4 C3 H3B 109.4 . . ? H3A C3 H3B 108 . . ? N1 C4 C3 109.0(2) . . ? N1 C4 H4A 109.9 . . ? C3 C4 H4A 109.9 . . ? N1 C4 H4B 109.9 . . ? C3 C4 H4B 109.9 . . ? H4A C4 H4B 108.3 . . ? N1 C5 C12 123.3(2) . . ? N1 C5 C6 117.3(2) . . ? C12 C5 C6 119.4(2) . . ? C7 C6 C11 119.6(3) . . ? C7 C6 C5 119.6(2) . . ? C11 C6 C5 120.6(2) . . ? C8 C7 C6 120.1(3) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C9 C8 C7 118.3(3) . . ? C9 C8 H8 120.9 . . ? C7 C8 H8 120.9 . . ? F1 C9 C10 118.1(3) . . ? F1 C9 C8 118.2(3) . . ? C10 C9 C8 123.7(3) . . ? C9 C10 C11 117.6(3) . . ? C9 C10 H10 121.2 . . ? C11 C10 H10 121.2 . . ? C10 C11 C6 120.6(3) . . ? C10 C11 H11 119.7 . . ? C6 C11 H11 119.7 . . ? C13 C12 C5 121.3(2) . . ? C13 C12 H12 119.4 . . ? C5 C12 H12 119.4 . . ? C12 C13 C14 124.9(2) . . ? C12 C13 H13 117.5 . . ? C14 C13 H13 117.5 . . ? C15 C14 C13 121.3(2) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? N2 C15 C14 123.1(2) . . ? N2 C15 C16 118.0(2) . . ? C14 C15 C16 118.9(2) . . ? C21 C16 C17 119.4(3) . . ? C21 C16 C15 120.6(2) . . ? C17 C16 C15 120.0(2) . . ? C18 C17 C16 121.1(3) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C19 C18 C17 117.3(3) . . ? C19 C18 H18 121.3 . . ? C17 C18 H18 121.3 . . ? F2 C19 C18 117.2(3) . . ? F2 C19 C20 119.3(3) . . ? C18 C19 C20 123.4(3) . . ? C19 C20 C21 119.0(3) . . ? C19 C20 H20 120.5 . . ? C21 C20 H20 120.5 . . ? C20 C21 C16 119.7(3) . . ? C20 C21 H21 120.2 . . ? C16 C21 H21 120.2 . . ? N2 C22 C23 112.0(2) . . ? N2 C22 H22A 109.2 . . ? C23 C22 H22A 109.2 . . ? N2 C22 H22B 109.2 . . ? C23 C22 H22B 109.2 . . ? H22A C22 H22B 107.9 . . ? N3 C23 C22 109.2(2) . . ? N3 C23 H23A 109.8 . . ? C22 C23 H23A 109.8 . . ? N3 C23 H23B 109.8 . . ? C22 C23 H23B 109.8 . . ? H23A C23 H23B 108.3 . . ? N2 C24 C25 109.5(2) . . ? N2 C24 H24A 109.8 . . ? C25 C24 H24A 109.8 . . ? N2 C24 H24B 109.8 . . ? C25 C24 H24B 109.8 . . ? H24A C24 H24B 108.2 . . ? N3 C25 C24 110.3(2) . . ? N3 C25 H25A 109.6 . . ? C24 C25 H25A 109.6 . . ? N3 C25 H25B 109.6 . . ? C24 C25 H25B 109.6 . . ? H25A C25 H25B 108.1 . . ? C27 C26 N3 124.1(2) . . ? C27 C26 C30 117.3(2) . . ? N3 C26 C30 118.6(2) . . ? N4 C29 C34 117.4(2) . . ? N4 C29 C30 123.5(2) . . ? C34 C29 C30 119.1(2) . . ? C29 C30 C31 118.6(2) . . ? C29 C30 C26 117.4(2) . . ? C31 C30 C26 123.9(2) . . ? C32 C31 C30 121.3(2) . . ? C32 C31 H31 119.3 . . ? C30 C31 H31 119.3 . . ? C31 C32 C33 118.6(3) . . ? C31 C32 H32 120.7 . . ? C33 C32 H32 120.7 . . ? C34 C33 C32 122.4(2) . . ? C34 C33 Cl1 120.8(2) . . ? C32 C33 Cl1 116.8(2) . . ? C33 C34 C29 119.5(2) . . ? C33 C34 H34 120.3 . . ? C29 C34 H34 120.3 . . ? C5 N1 C2 123.9(2) . . ? C5 N1 C4 123.4(2) . . ? C2 N1 C4 112.2(2) . . ? C15 N2 C24 124.2(2) . . ? C15 N2 C22 124.0(2) . . ? C24 N2 C22 111.52(19) . . ? C26 N3 C23 116.9(2) . . ? C26 N3 C25 118.8(2) . . ? C23 N3 C25 109.23(19) . . ? C3 O1 C1 110.4(2) . . ? F4' B1 F5 122.7(5) . . ? F4' B1 F3 116.7(4) . . ? F5 B1 F3 117.2(4) . . ? F4' B1 F5' 113.3(6) . . ? F3 B1 F5' 107.5(5) . . ? F4' B1 F6 62.0(5) . . ? F5 B1 F6 111.6(5) . . ? F3 B1 F6 112.5(3) . . ? F5' B1 F6 136.5(5) . . ? F5 B1 F4 109.5(4) . . ? F3 B1 F4 105.0(3) . . ? F5' B1 F4 86.0(4) . . ? F6 B1 F4 99.2(4) . . ? F4' B1 F6' 112.5(5) . . ? F5 B1 F6' 70.5(4) . . ? F3 B1 F6' 104.5(3) . . ? F5' B1 F6' 100.8(4) . . ? F6 B1 F6' 53.5(3) . . ? F4 B1 F6' 146.1(4) . . ? C28 N4 C29 116.9(2) . . ? C26 C27 C28 120.4(2) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? N4 C28 C27 124.2(3) . . ? N4 C28 H28 117.9 . . ? C27 C28 H28 117.9 . . ? #===END