Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2010 data_New_Global_Publ_Block #TrackingRef '- ChemComm_Bernhard.cif' _journal_coden_Cambridge 182 # Added by publCIF - use a unique identifier for each data block #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'Franck Denat' # Name of author for correspondence _publ_contact_author_address # Address of author for correspondence ; ICMUB UMR 5260 CNRS - Univ. de Bourgogne 9 avenue AlainSavary 21078 Dijon Cedex France ; _publ_contact_author_email Franck.Denat@u-bourgogne.fr _publ_contact_author_fax '+33 (0)3 80 39 61 17' _publ_contact_author_phone '+33 (0)3 80 39 61 15' _publ_contact_letter ; Please consider this CIF for publication. I certify that this contibution is the original work of those listed as authors; that it has not been published before (in any language or medium) and is not being considered for publication elsewhere; that all authors concur with and are aware of the submission; that all workers involved in the study are listed as authors or given proper credit in the acknowledgements; that I have obtained permission for and acknowledged the source of any excerpts from other copyright works; and that to the best of my knowledge the paper contains no statements which are libellous, unlawful or in any way actionable. All coauthors have made significant scientific contributions to the work reported, including the ideas and their execution, and share responsibility and accountability for the results. ; _publ_requested_journal 'Chem. Comm.' _publ_requested_category ? #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; First bodipy-DOTA derivative and its corresponding In(III), Ga(III) and Cu(II) complexes: a new precursor for bimodal imaging ; _publ_section_title_footnote # remove if not required . # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. # NB if using publCIF, the Author database tool might prove useful # (see the Tools menu in publCIF) loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Bernhard, Claire' ; ICMUB UMR 5260 CNRS - Univ. de Bourgogne 9 avenue AlainSavary 21078 Dijon Cedex France ; ; ? ; 'Goze, Christine' ; ICMUB UMR 5260 CNRS - Univ. de Bourgogne 9 avenue AlainSavary 21078 Dijon Cedex France ; . 'Rousselin, Yoann' ; ICMUB UMR 5260 CNRS - Univ. de Bourgogne 9 avenue AlainSavary 21078 Dijon Cedex France ; . 'Denat, Franck' ; ICMUB UMR 5260 CNRS - Univ. de Bourgogne 9 avenue AlainSavary 21078 Dijon Cedex France ; . #============================================================================== # TEXT _publ_section_synopsis . _publ_section_abstract ; (type here to add abstract) ; _publ_section_comment ; The stucture of the title compound, (I), is shown below. Dimensions are available in the archived CIF. For related literature, see [type here to add references to related literature]. ; _publ_section_acknowledgements # remove if not required ; (type here to add acknowledgements) ; _publ_section_references ; ? ; _publ_section_figure_captions ; ; _publ_section_exptl_prep ; (type here to add preparation details) ; _publ_section_exptl_refinement ; (type here to add refinement details) ; #============================================================================== _publ_manuscript_text # Used for convenience to store draft or replaced versions # of the abstract, comment etc. # Its contents will not be output ; ? ; #============================================================================== # Formatted by publCIF data_10cb732 _database_code_depnum_ccdc_archive 'CCDC 785489' #TrackingRef '- ChemComm_Bernhard.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C35 H41 B F2 N6 O4, C H2 Cl2' _chemical_formula_sum 'C36 H43 B Cl2 F2 N6 O4' _chemical_formula_weight 743.47 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 0.0000 0.0000 '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' O O 0.0106 0.0060 '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' B B 0.0013 0.0007 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5109(4) _cell_length_b 12.5631(6) _cell_length_c 16.3648(8) _cell_angle_alpha 101.572(2) _cell_angle_beta 103.112(3) _cell_angle_gamma 99.345(3) _cell_volume 1820.86(15) _cell_formula_units_Z 2 _cell_measurement_temperature 115(2) _cell_measurement_reflns_used 7085 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description Prism _exptl_crystal_colour red _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 780 _exptl_absorpt_coefficient_mu 0.237 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 115(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 'Nonius Kappa APEX-II' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13572 _diffrn_reflns_av_R_equivalents 0.0477 _diffrn_reflns_av_sigmaI/netI 0.0663 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 27.54 _reflns_number_total 8217 _reflns_number_gt 5507 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia,1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0402P)^2^+6.3481P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8217 _refine_ls_number_parameters 467 _refine_ls_number_restraints 0 _refine_ls_number_constraints 8 _refine_ls_R_factor_all 0.1499 _refine_ls_R_factor_gt 0.0979 _refine_ls_wR_factor_ref 0.2229 _refine_ls_wR_factor_gt 0.1917 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.134 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.000 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 0.8164(4) 0.0027(4) 0.8938(3) 0.0291(9) Uani 1 1 d . . . C2 C 0.8085(4) -0.0832(4) 0.9371(3) 0.0297(9) Uani 1 1 d . . . C3 C 0.7753(4) -0.0413(4) 1.0142(3) 0.0279(9) Uani 1 1 d . . . C4 C 0.7652(4) 0.0713(4) 1.0173(3) 0.0261(9) Uani 1 1 d . . . C5 C 0.7455(4) 0.1551(4) 1.0816(3) 0.0263(9) Uani 1 1 d . . . C6 C 0.7528(5) 0.2644(4) 1.0732(3) 0.0276(9) Uani 1 1 d . . . C7 C 0.7427(5) 0.3633(4) 1.1299(3) 0.0303(9) Uani 1 1 d . . . C8 C 0.7661(5) 0.4495(4) 1.0897(3) 0.0317(10) Uani 1 1 d . . . C9 C 0.7880(5) 0.4034(4) 1.0087(3) 0.0321(10) Uani 1 1 d . . . C10 C 0.8463(5) -0.0014(4) 0.8075(3) 0.0394(11) Uani 1 1 d . . . H10A H 0.7718 0.0279 0.7719 0.059 Uiso 1 1 calc R . . H10B H 0.8417 -0.0787 0.7785 0.059 Uiso 1 1 calc R . . H10C H 0.9449 0.0437 0.8155 0.059 Uiso 1 1 calc R . . C11 C 0.8280(5) -0.1986(4) 0.9039(3) 0.0333(10) Uani 1 1 d . . . H11A H 0.8810 -0.2246 0.9529 0.040 Uiso 1 1 calc R . . H11B H 0.8899 -0.1966 0.8628 0.040 Uiso 1 1 calc R . . C12 C 0.6809(5) -0.2814(4) 0.8584(3) 0.0410(11) Uani 1 1 d . . . H12A H 0.6209 -0.2862 0.8995 0.061 Uiso 1 1 calc R . . H12B H 0.6997 -0.3548 0.8369 0.061 Uiso 1 1 calc R . . H12C H 0.6278 -0.2561 0.8097 0.061 Uiso 1 1 calc R . . C13 C 0.7526(5) -0.1090(4) 1.0782(3) 0.0335(10) Uani 1 1 d . . . H13A H 0.6466 -0.1383 1.0684 0.050 Uiso 1 1 calc R . . H13B H 0.7936 -0.0618 1.1372 0.050 Uiso 1 1 calc R . . H13C H 0.8030 -0.1710 1.0707 0.050 Uiso 1 1 calc R . . C14 C 0.7112(5) 0.3777(4) 1.2172(3) 0.0335(10) Uani 1 1 d . . . H14A H 0.8015 0.3804 1.2614 0.050 Uiso 1 1 calc R . . H14B H 0.6339 0.3148 1.2158 0.050 Uiso 1 1 calc R . . H14C H 0.6776 0.4472 1.2312 0.050 Uiso 1 1 calc R . . C15 C 0.7673(6) 0.5711(4) 1.1246(4) 0.0411(11) Uani 1 1 d . . . H15A H 0.8019 0.5897 1.1886 0.049 Uiso 1 1 calc R . . H15B H 0.8391 0.6175 1.1037 0.049 Uiso 1 1 calc R . . C16 C 0.6178(6) 0.6004(5) 1.0984(4) 0.0520(14) Uani 1 1 d . . . H16A H 0.5865 0.5885 1.0353 0.078 Uiso 1 1 calc R . . H16B H 0.6252 0.6787 1.1259 0.078 Uiso 1 1 calc R . . H16C H 0.5451 0.5530 1.1170 0.078 Uiso 1 1 calc R . . C17 C 0.8115(6) 0.4607(4) 0.9399(3) 0.0402(11) Uani 1 1 d . . . H17A H 0.8914 0.4367 0.9174 0.060 Uiso 1 1 calc R . . H17B H 0.8384 0.5414 0.9643 0.060 Uiso 1 1 calc R . . H17C H 0.7202 0.4417 0.8927 0.060 Uiso 1 1 calc R . . C18 C 0.7244(4) 0.1276(3) 1.1631(2) 0.0236(8) Uani 1 1 d . . . C19 C 0.5907(5) 0.0680(4) 1.1670(3) 0.0286(9) Uani 1 1 d . . . H19 H 0.5083 0.0458 1.1173 0.034 Uiso 1 1 calc R . . C20 C 0.5776(4) 0.0410(4) 1.2433(3) 0.0265(9) Uani 1 1 d . . . H20 H 0.4861 0.0000 1.2457 0.032 Uiso 1 1 calc R . . C21 C 0.6979(4) 0.0737(3) 1.3168(3) 0.0237(8) Uani 1 1 d . . . C22 C 0.8313(4) 0.1341(3) 1.3131(2) 0.0232(8) Uani 1 1 d . . . H22 H 0.9135 0.1575 1.3629 0.028 Uiso 1 1 calc R . . C23 C 0.8439(5) 0.1603(3) 1.2360(3) 0.0257(9) Uani 1 1 d . . . H23 H 0.9353 0.2010 1.2332 0.031 Uiso 1 1 calc R . . C24 C 0.6758(4) 0.0436(3) 1.3982(3) 0.0228(8) Uani 1 1 d . . . C25 C 0.7882(4) 0.0432(3) 1.5481(2) 0.0216(8) Uani 1 1 d . . . H25 H 0.6965 0.0636 1.5604 0.026 Uiso 1 1 calc R . . C26 C 0.9242(4) 0.1156(3) 1.6187(3) 0.0248(8) Uani 1 1 d . . . H26A H 0.9252 0.0941 1.6738 0.030 Uiso 1 1 calc R . . H26B H 1.0148 0.1012 1.6026 0.030 Uiso 1 1 calc R . . C27 C 0.9263(5) 0.2385(3) 1.6323(3) 0.0263(9) Uani 1 1 d . . . C28 C 0.8662(6) 0.2916(4) 1.6950(3) 0.0378(11) Uani 1 1 d . . . H28 H 0.8272 0.2505 1.7307 0.045 Uiso 1 1 calc R . . C29 C 0.8622(6) 0.4021(4) 1.7061(3) 0.0397(11) Uani 1 1 d . . . H29 H 0.8228 0.4382 1.7497 0.048 Uiso 1 1 calc R . . C30 C 0.9170(5) 0.4601(4) 1.6521(3) 0.0309(9) Uani 1 1 d . . . C31 C 0.9814(5) 0.4108(4) 1.5913(3) 0.0318(10) Uani 1 1 d . . . H31 H 1.0218 0.4526 1.5564 0.038 Uiso 1 1 calc R . . C32 C 0.9863(5) 0.3004(3) 1.5817(3) 0.0288(9) Uani 1 1 d . . . H32 H 1.0310 0.2659 1.5401 0.035 Uiso 1 1 calc R . . C34 C 0.7850(4) -0.0789(3) 1.5492(2) 0.0227(8) Uani 1 1 d . B . C35 C 0.6548(5) -0.2484(4) 1.5725(4) 0.0409(12) Uani 1 1 d . B . H35A H 0.7395 -0.2525 1.6189 0.049 Uiso 1 1 calc R . . H35B H 0.6586 -0.2966 1.5175 0.049 Uiso 1 1 calc R . . C36 C 0.5152(6) -0.2897(5) 1.5926(5) 0.0593(16) Uani 1 1 d . . . H36A H 0.5130 -0.3656 1.6014 0.071 Uiso 1 1 calc R A 1 H36B H 0.5105 -0.2408 1.6470 0.071 Uiso 1 1 calc R A 1 C37A C 0.5177(11) 0.7311(9) 1.3216(8) 0.0637(4) Uani 0.835(3) 1 d P B 1 H37A H 0.4444 0.7401 1.2713 0.076 Uiso 0.835(3) 1 calc PR B 1 H37B H 0.5000 0.7732 1.3750 0.076 Uiso 0.835(3) 1 calc PR B 1 C37B C 0.543(6) 0.732(5) 1.308(4) 0.0637(4) Uani 0.165(3) 1 d P B 2 H37C H 0.5326 0.7827 1.3602 0.076 Uiso 0.165(3) 1 calc PR B 2 H37D H 0.4498 0.7177 1.2621 0.076 Uiso 0.165(3) 1 calc PR B 2 N1 N 0.7916(4) 0.0956(3) 0.9416(2) 0.0278(8) Uani 1 1 d . . . N2 N 0.7802(4) 0.2924(3) 0.9987(2) 0.0285(8) Uani 1 1 d . . . N3 N 0.6674(4) -0.1334(3) 1.5647(2) 0.0305(8) Uani 1 1 d . . . H3 H 0.5946 -0.0998 1.5705 0.037 Uiso 1 1 calc R B . N4A N 0.3938(6) -0.2922(5) 1.5264(4) 0.0589(16) Uani 0.835(3) 1 d P B 1 H4A1 H 0.4064 -0.2707 1.4802 0.071 Uiso 0.835(3) 1 calc PR B 1 H4A2 H 0.3039 -0.3153 1.5306 0.071 Uiso 0.835(3) 1 calc PR B 1 N4B N 0.445(3) -0.411(2) 1.564(2) 0.0589(16) Uani 0.165(3) 1 d P B 2 H4B1 H 0.3629 -0.4354 1.5213 0.071 Uiso 0.165(3) 1 calc PR B 2 H4B2 H 0.4845 -0.4583 1.5897 0.071 Uiso 0.165(3) 1 calc PR B 2 N5 N 0.9062(4) 0.5761(3) 1.6601(3) 0.0370(9) Uani 1 1 d . . . N6 N 0.7976(3) 0.0607(3) 1.4638(2) 0.0215(7) Uani 1 1 d . . . H6 H 0.8850 0.0829 1.4558 0.026 Uiso 1 1 calc R . . O1 O 0.5507(3) 0.0066(2) 1.40415(18) 0.0259(6) Uani 1 1 d . . . O2 O 0.8915(3) -0.1197(2) 1.53864(19) 0.0290(7) Uani 1 1 d . . . O3 O 0.9453(4) 0.6238(3) 1.6078(2) 0.0432(8) Uani 1 1 d . . . O4 O 0.8587(4) 0.6215(3) 1.7183(3) 0.0509(10) Uani 1 1 d . . . F1 F 0.6882(3) 0.2040(2) 0.84605(16) 0.0397(6) Uani 1 1 d . . . F2 F 0.9364(3) 0.2465(2) 0.90554(17) 0.0392(6) Uani 1 1 d . . . B1 B 0.7988(5) 0.2105(4) 0.9200(3) 0.0300(11) Uani 1 1 d . . . Cl1A Cl 0.6956(2) 0.78367(17) 1.31663(17) 0.0637(4) Uani 0.835(3) 1 d P B 1 Cl2A Cl 0.4954(3) 0.58722(18) 1.32150(15) 0.0637(4) Uani 0.835(3) 1 d P B 1 Cl1B Cl 0.6957(12) 0.8013(9) 1.2723(9) 0.0637(4) Uani 0.165(3) 1 d P B 2 Cl2B Cl 0.5665(13) 0.6112(9) 1.3321(8) 0.0637(4) Uani 0.165(3) 1 d P B 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 0.0232(19) 0.039(3) 0.023(2) 0.0079(18) 0.0054(17) 0.0010(18) C2 0.024(2) 0.037(2) 0.025(2) 0.0053(18) 0.0060(17) 0.0026(18) C3 0.025(2) 0.033(2) 0.025(2) 0.0093(18) 0.0054(17) 0.0032(17) C4 0.0228(19) 0.033(2) 0.023(2) 0.0130(17) 0.0061(16) -0.0002(17) C5 0.025(2) 0.031(2) 0.022(2) 0.0110(17) 0.0038(16) 0.0012(17) C6 0.028(2) 0.034(2) 0.023(2) 0.0150(18) 0.0071(17) 0.0053(18) C7 0.028(2) 0.033(2) 0.029(2) 0.0099(19) 0.0055(18) 0.0058(18) C8 0.027(2) 0.032(2) 0.037(2) 0.015(2) 0.0074(19) 0.0037(18) C9 0.031(2) 0.035(3) 0.036(2) 0.021(2) 0.0082(19) 0.0078(19) C10 0.041(3) 0.057(3) 0.027(2) 0.014(2) 0.015(2) 0.014(2) C11 0.031(2) 0.043(3) 0.028(2) 0.008(2) 0.0094(19) 0.011(2) C12 0.044(3) 0.038(3) 0.041(3) 0.006(2) 0.015(2) 0.008(2) C13 0.041(2) 0.031(2) 0.031(2) 0.0119(19) 0.013(2) 0.005(2) C14 0.041(2) 0.033(2) 0.029(2) 0.0091(19) 0.013(2) 0.008(2) C15 0.044(3) 0.033(3) 0.052(3) 0.019(2) 0.016(2) 0.010(2) C16 0.053(3) 0.043(3) 0.064(4) 0.021(3) 0.013(3) 0.012(3) C17 0.043(3) 0.046(3) 0.044(3) 0.030(2) 0.017(2) 0.014(2) C18 0.030(2) 0.025(2) 0.0207(19) 0.0102(16) 0.0084(16) 0.0101(17) C19 0.027(2) 0.038(3) 0.0199(19) 0.0113(18) 0.0033(16) 0.0040(18) C20 0.025(2) 0.033(2) 0.025(2) 0.0114(18) 0.0113(17) 0.0055(17) C21 0.030(2) 0.022(2) 0.024(2) 0.0107(16) 0.0113(17) 0.0089(16) C22 0.0245(19) 0.027(2) 0.0191(18) 0.0086(16) 0.0060(16) 0.0052(16) C23 0.028(2) 0.030(2) 0.026(2) 0.0149(17) 0.0127(17) 0.0085(17) C24 0.029(2) 0.021(2) 0.0235(19) 0.0080(16) 0.0117(17) 0.0108(16) C25 0.029(2) 0.024(2) 0.0205(19) 0.0126(16) 0.0138(16) 0.0121(16) C26 0.030(2) 0.024(2) 0.022(2) 0.0083(16) 0.0063(17) 0.0078(17) C27 0.034(2) 0.023(2) 0.021(2) 0.0047(16) 0.0072(17) 0.0059(17) C28 0.060(3) 0.030(2) 0.031(2) 0.0082(19) 0.027(2) 0.008(2) C29 0.057(3) 0.034(3) 0.035(3) 0.006(2) 0.029(2) 0.011(2) C30 0.039(2) 0.028(2) 0.028(2) 0.0063(18) 0.0125(19) 0.0098(19) C31 0.044(3) 0.024(2) 0.032(2) 0.0091(18) 0.016(2) 0.0083(19) C32 0.039(2) 0.026(2) 0.027(2) 0.0085(17) 0.0160(19) 0.0080(18) C34 0.0262(19) 0.023(2) 0.0219(19) 0.0081(16) 0.0093(16) 0.0078(16) C35 0.039(3) 0.031(3) 0.062(3) 0.023(2) 0.021(2) 0.010(2) C36 0.054(3) 0.043(3) 0.093(5) 0.028(3) 0.034(3) 0.008(3) C37A 0.0529(8) 0.0501(7) 0.0788(10) 0.0009(7) 0.0094(8) 0.0156(6) C37B 0.0529(8) 0.0501(7) 0.0788(10) 0.0009(7) 0.0094(8) 0.0156(6) N1 0.0285(18) 0.037(2) 0.0207(17) 0.0127(15) 0.0075(14) 0.0064(15) N2 0.0302(18) 0.033(2) 0.0259(18) 0.0166(16) 0.0080(15) 0.0062(15) N3 0.0314(19) 0.030(2) 0.041(2) 0.0191(17) 0.0175(17) 0.0118(16) N4A 0.039(3) 0.047(3) 0.086(4) 0.027(3) 0.007(3) -0.004(2) N4B 0.039(3) 0.047(3) 0.086(4) 0.027(3) 0.007(3) -0.004(2) N5 0.043(2) 0.029(2) 0.040(2) 0.0041(17) 0.0161(18) 0.0070(17) N6 0.0226(16) 0.0279(18) 0.0201(16) 0.0118(14) 0.0103(13) 0.0086(14) O1 0.0254(14) 0.0322(16) 0.0244(14) 0.0113(12) 0.0111(12) 0.0069(12) O2 0.0321(15) 0.0304(16) 0.0341(16) 0.0151(13) 0.0165(13) 0.0143(13) O3 0.061(2) 0.0308(18) 0.047(2) 0.0169(16) 0.0223(18) 0.0153(16) O4 0.066(2) 0.033(2) 0.060(2) 0.0021(17) 0.038(2) 0.0135(18) F1 0.0438(15) 0.0510(18) 0.0245(13) 0.0184(12) 0.0025(11) 0.0091(13) F2 0.0371(14) 0.0488(17) 0.0412(15) 0.0237(13) 0.0198(12) 0.0072(12) B1 0.029(2) 0.039(3) 0.024(2) 0.017(2) 0.007(2) 0.004(2) Cl1A 0.0529(8) 0.0501(7) 0.0788(10) 0.0009(7) 0.0094(8) 0.0156(6) Cl2A 0.0529(8) 0.0501(7) 0.0788(10) 0.0009(7) 0.0094(8) 0.0156(6) Cl1B 0.0529(8) 0.0501(7) 0.0788(10) 0.0009(7) 0.0094(8) 0.0156(6) Cl2B 0.0529(8) 0.0501(7) 0.0788(10) 0.0009(7) 0.0094(8) 0.0156(6) _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 N1 1.355(6) . ? C1 C2 1.406(6) . ? C1 C10 1.495(6) . ? C2 C3 1.392(6) . ? C2 C11 1.500(6) . ? C3 C4 1.425(6) . ? C3 C13 1.505(6) . ? C4 C5 1.400(6) . ? C4 N1 1.400(5) . ? C5 C6 1.400(6) . ? C5 C18 1.491(5) . ? C6 N2 1.402(5) . ? C6 C7 1.424(6) . ? C7 C8 1.390(6) . ? C7 C14 1.507(6) . ? C8 C9 1.411(6) . ? C8 C15 1.517(7) . ? C9 N2 1.358(6) . ? C9 C17 1.492(6) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.529(7) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.516(7) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C23 1.385(6) . ? C18 C19 1.388(6) . ? C19 C20 1.385(5) . ? C19 H19 0.9500 . ? C20 C21 1.396(6) . ? C20 H20 0.9500 . ? C21 C22 1.390(5) . ? C21 C24 1.504(5) . ? C22 C23 1.392(5) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 O1 1.238(5) . ? C24 N6 1.343(5) . ? C25 N6 1.458(4) . ? C25 C34 1.533(5) . ? C25 C26 1.534(6) . ? C25 H25 1.0000 . ? C26 C27 1.511(6) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.393(6) . ? C27 C32 1.396(5) . ? C28 C29 1.372(6) . ? C28 H28 0.9500 . ? C29 C30 1.387(6) . ? C29 H29 0.9500 . ? C30 C31 1.380(6) . ? C30 N5 1.460(6) . ? C31 C32 1.373(6) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C34 O2 1.237(5) . ? C34 N3 1.317(5) . ? C35 N3 1.464(6) . ? C35 C36 1.477(7) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 N4A 1.384(8) . ? C36 N4B 1.49(3) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37A Cl1A 1.740(9) . ? C37A Cl2A 1.785(12) . ? C37A H37A 0.9900 . ? C37A H37B 0.9900 . ? C37B Cl2B 1.68(6) . ? C37B Cl1B 1.84(5) . ? C37B H37C 0.9900 . ? C37B H37D 0.9900 . ? N1 B1 1.548(6) . ? N2 B1 1.542(6) . ? N3 H3 0.8800 . ? N4A H4A1 0.8800 . ? N4A H4A2 0.8800 . ? N4B H4B1 0.8800 . ? N4B H4B2 0.8800 . ? N5 O4 1.223(5) . ? N5 O3 1.228(5) . ? N6 H6 0.8800 . ? F1 B1 1.390(5) . ? F2 B1 1.402(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 N1 C1 C2 110.3(4) . . ? N1 C1 C10 122.0(4) . . ? C2 C1 C10 127.7(4) . . ? C3 C2 C1 107.0(4) . . ? C3 C2 C11 127.3(4) . . ? C1 C2 C11 125.6(4) . . ? C2 C3 C4 107.2(4) . . ? C2 C3 C13 123.6(4) . . ? C4 C3 C13 129.2(4) . . ? C5 C4 N1 120.0(4) . . ? C5 C4 C3 132.0(4) . . ? N1 C4 C3 107.9(4) . . ? C4 C5 C6 121.9(4) . . ? C4 C5 C18 118.6(4) . . ? C6 C5 C18 119.4(4) . . ? C5 C6 N2 119.9(4) . . ? C5 C6 C7 132.3(4) . . ? N2 C6 C7 107.8(4) . . ? C8 C7 C6 107.2(4) . . ? C8 C7 C14 123.9(4) . . ? C6 C7 C14 128.8(4) . . ? C7 C8 C9 107.3(4) . . ? C7 C8 C15 127.2(4) . . ? C9 C8 C15 125.5(4) . . ? N2 C9 C8 109.7(4) . . ? N2 C9 C17 122.1(4) . . ? C8 C9 C17 128.1(4) . . ? C1 C10 H10A 109.5 . . ? C1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C2 C11 C12 112.7(4) . . ? C2 C11 H11A 109.1 . . ? C12 C11 H11A 109.1 . . ? C2 C11 H11B 109.1 . . ? C12 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C3 C13 H13A 109.5 . . ? C3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C7 C14 H14A 109.5 . . ? C7 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C7 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C8 113.8(4) . . ? C16 C15 H15A 108.8 . . ? C8 C15 H15A 108.8 . . ? C16 C15 H15B 108.8 . . ? C8 C15 H15B 108.8 . . ? H15A C15 H15B 107.7 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C9 C17 H17A 109.5 . . ? C9 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C9 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C23 C18 C19 119.7(4) . . ? C23 C18 C5 118.4(4) . . ? C19 C18 C5 121.9(4) . . ? C20 C19 C18 120.0(4) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C21 120.5(4) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C22 C21 C20 119.5(4) . . ? C22 C21 C24 122.6(4) . . ? C20 C21 C24 117.9(4) . . ? C21 C22 C23 119.6(4) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? C18 C23 C22 120.7(4) . . ? C18 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? O1 C24 N6 122.1(3) . . ? O1 C24 C21 121.1(4) . . ? N6 C24 C21 116.8(3) . . ? N6 C25 C34 110.3(3) . . ? N6 C25 C26 109.8(3) . . ? C34 C25 C26 108.1(3) . . ? N6 C25 H25 109.5 . . ? C34 C25 H25 109.5 . . ? C26 C25 H25 109.5 . . ? C27 C26 C25 112.6(3) . . ? C27 C26 H26A 109.1 . . ? C25 C26 H26A 109.1 . . ? C27 C26 H26B 109.1 . . ? C25 C26 H26B 109.1 . . ? H26A C26 H26B 107.8 . . ? C28 C27 C32 118.8(4) . . ? C28 C27 C26 120.4(4) . . ? C32 C27 C26 120.8(4) . . ? C29 C28 C27 121.2(4) . . ? C29 C28 H28 119.4 . . ? C27 C28 H28 119.4 . . ? C28 C29 C30 118.5(4) . . ? C28 C29 H29 120.7 . . ? C30 C29 H29 120.7 . . ? C31 C30 C29 121.7(4) . . ? C31 C30 N5 119.3(4) . . ? C29 C30 N5 119.1(4) . . ? C32 C31 C30 119.1(4) . . ? C32 C31 H31 120.4 . . ? C30 C31 H31 120.4 . . ? C31 C32 C27 120.6(4) . . ? C31 C32 H32 119.7 . . ? C27 C32 H32 119.7 . . ? O2 C34 N3 123.8(4) . . ? O2 C34 C25 119.9(3) . . ? N3 C34 C25 116.3(3) . . ? N3 C35 C36 111.3(4) . . ? N3 C35 H35A 109.4 . . ? C36 C35 H35A 109.4 . . ? N3 C35 H35B 109.4 . . ? C36 C35 H35B 109.4 . . ? H35A C35 H35B 108.0 . . ? N4A C36 C35 111.2(5) . . ? N4A C36 N4B 78.3(13) . . ? C35 C36 N4B 120.0(12) . . ? N4A C36 H36A 109.4 . . ? C35 C36 H36A 109.4 . . ? N4A C36 H36B 109.4 . . ? C35 C36 H36B 109.4 . . ? N4B C36 H36B 123.1 . . ? H36A C36 H36B 108.0 . . ? Cl1A C37A Cl2A 110.1(5) . . ? Cl1A C37A H37A 109.6 . . ? Cl2A C37A H37A 109.6 . . ? Cl1A C37A H37B 109.6 . . ? Cl2A C37A H37B 109.6 . . ? H37A C37A H37B 108.2 . . ? Cl2B C37B Cl1B 114(2) . . ? Cl2B C37B H37C 108.8 . . ? Cl1B C37B H37C 108.8 . . ? Cl2B C37B H37D 108.8 . . ? Cl1B C37B H37D 108.8 . . ? H37C C37B H37D 107.7 . . ? C1 N1 C4 107.6(4) . . ? C1 N1 B1 127.0(3) . . ? C4 N1 B1 125.3(4) . . ? C9 N2 C6 107.9(4) . . ? C9 N2 B1 126.7(3) . . ? C6 N2 B1 125.4(4) . . ? C34 N3 C35 121.6(4) . . ? C34 N3 H3 119.2 . . ? C35 N3 H3 119.2 . . ? C36 N4A H4A1 120.0 . . ? C36 N4A H4A2 120.0 . . ? H4A1 N4A H4A2 120.0 . . ? C36 N4B H4B1 120.0 . . ? C36 N4B H4B2 120.0 . . ? H4B1 N4B H4B2 120.0 . . ? O4 N5 O3 122.9(4) . . ? O4 N5 C30 118.8(4) . . ? O3 N5 C30 118.3(4) . . ? C24 N6 C25 121.5(3) . . ? C24 N6 H6 119.3 . . ? C25 N6 H6 119.3 . . ? F1 B1 F2 108.7(3) . . ? F1 B1 N2 110.6(4) . . ? F2 B1 N2 109.9(4) . . ? F1 B1 N1 110.8(4) . . ? F2 B1 N1 109.4(4) . . ? N2 B1 N1 107.4(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3 O1 0.88 2.01 2.886(4) 172.2 2_658 N4B H4B2 Cl2B 0.88 2.55 3.31(3) 143.8 2_658 N6 H6 O2 0.88 2.08 2.941(4) 166.5 2_758 _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.416 _refine_diff_density_min -0.955 _refine_diff_density_rms 0.081