# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_jmlgv130418 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C56 H44 Ca2 F12 N12 O16 S4' _chemical_formula_sum 'C56 H44 Ca2 F12 N12 O16 S4' _chemical_formula_weight 1577.43 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ca Ca 0.2262 0.3064 '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 11.2305(6) _cell_length_b 12.1307(7) _cell_length_c 13.8812(8) _cell_angle_alpha 97.6830(10) _cell_angle_beta 111.4790(10) _cell_angle_gamma 105.0070(10) _cell_volume 1643.89(16) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used multi-scan _cell_measurement_theta_min 0.9151 _cell_measurement_theta_max 0.9447 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.593 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 804 _exptl_absorpt_coefficient_mu 0.411 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9151 _exptl_absorpt_correction_T_max 0.9447 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33140 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 29.06 _reflns_number_total 8774 _reflns_number_gt 6669 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^ > 2\s(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^)+(0.1567P)^2^+8.1790P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8774 _refine_ls_number_parameters 460 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1359 _refine_ls_R_factor_gt 0.1100 _refine_ls_wR_factor_ref 0.3117 _refine_ls_wR_factor_gt 0.2875 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.000 _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 0.0370(6) 0.3406(5) 0.5524(4) 0.0405(11) Uani 1 1 d . . . H1 H -0.0525 0.3056 0.5461 0.049 Uiso 1 1 calc R . . C2 C 0.1084(7) 0.4561(5) 0.6112(5) 0.0476(13) Uani 1 1 d . . . H2 H 0.0671 0.5001 0.6425 0.057 Uiso 1 1 calc R . . C3 C 0.2382(7) 0.5065(5) 0.6240(5) 0.0499(14) Uani 1 1 d . . . H3 H 0.2893 0.5850 0.6663 0.060 Uiso 1 1 calc R . . C4 C 0.2948(6) 0.4427(5) 0.5751(5) 0.0432(12) Uani 1 1 d . . . H4 H 0.3850 0.4766 0.5826 0.052 Uiso 1 1 calc R . . C5 C 0.2176(5) 0.3280(4) 0.5147(4) 0.0311(9) Uani 1 1 d . . . C6 C 0.2778(5) 0.2602(5) 0.4613(4) 0.0342(10) Uani 1 1 d . . . H6 H 0.3671 0.3013 0.4705 0.041 Uiso 1 1 calc R . . C7 C 0.0405(5) -0.0200(4) 0.3211(3) 0.0284(9) Uani 1 1 d . . . C8 C -0.0992(5) -0.0900(4) 0.3043(4) 0.0308(9) Uani 1 1 d . . . C9 C -0.1649(6) -0.1971(5) 0.2264(4) 0.0401(11) Uani 1 1 d . . . H9 H -0.1201 -0.2242 0.1867 0.048 Uiso 1 1 calc R . . C10 C -0.2960(6) -0.2641(5) 0.2070(5) 0.0449(12) Uani 1 1 d . . . H10 H -0.3410 -0.3373 0.1543 0.054 Uiso 1 1 calc R . . C11 C -0.3607(5) -0.2239(5) 0.2647(4) 0.0395(11) Uani 1 1 d . . . H11 H -0.4502 -0.2699 0.2513 0.047 Uiso 1 1 calc R . . C12 C -0.2970(5) -0.1183(5) 0.3410(4) 0.0371(10) Uani 1 1 d . . . H12 H -0.3429 -0.0913 0.3796 0.044 Uiso 1 1 calc R . . C13 C -0.1659(5) -0.0508(4) 0.3618(4) 0.0327(9) Uani 1 1 d . . . H13 H -0.1216 0.0220 0.4151 0.039 Uiso 1 1 calc R . . C14 C 0.7773(5) 0.0115(6) 0.0790(4) 0.0412(12) Uani 1 1 d . . . H14 H 0.7601 -0.0530 0.0231 0.049 Uiso 1 1 calc R . . C15 C 0.9015(5) 0.1027(6) 0.1219(5) 0.0476(15) Uani 1 1 d . . . H15 H 0.9677 0.1000 0.0952 0.057 Uiso 1 1 calc R . . C16 C 0.9279(6) 0.1957(6) 0.2022(5) 0.0505(15) Uani 1 1 d . . . H16 H 1.0125 0.2580 0.2320 0.061 Uiso 1 1 calc R . . C17 C 0.8323(6) 0.1986(5) 0.2394(5) 0.0450(12) Uani 1 1 d . . . H17 H 0.8489 0.2631 0.2952 0.054 Uiso 1 1 calc R . . C18 C 0.7088(5) 0.1053(4) 0.1946(4) 0.0327(9) Uani 1 1 d . . . C19 C 0.6094(5) 0.1100(4) 0.2389(4) 0.0349(10) Uani 1 1 d . . . H19 H 0.6348 0.1796 0.2927 0.042 Uiso 1 1 calc R . . C20 C 0.3273(4) -0.1453(4) 0.1119(3) 0.0279(8) Uani 1 1 d . . . C21 C 0.2845(5) -0.2594(4) 0.0326(3) 0.0313(9) Uani 1 1 d . . . C22 C 0.1518(6) -0.3376(4) 0.0018(4) 0.0375(10) Uani 1 1 d . . . H22 H 0.0946 -0.3165 0.0316 0.045 Uiso 1 1 calc R . . C23 C 0.1050(6) -0.4453(5) -0.0721(4) 0.0427(12) Uani 1 1 d . . . H23 H 0.0155 -0.4980 -0.0941 0.051 Uiso 1 1 calc R . . C24 C 0.1909(6) -0.4743(5) -0.1131(4) 0.0448(12) Uani 1 1 d . . . H24 H 0.1603 -0.5484 -0.1628 0.054 Uiso 1 1 calc R . . C25 C 0.3202(6) -0.3981(5) -0.0834(5) 0.0475(13) Uani 1 1 d . . . H25 H 0.3772 -0.4198 -0.1133 0.057 Uiso 1 1 calc R . . C26 C 0.3673(5) -0.2905(5) -0.0107(4) 0.0387(11) Uani 1 1 d . . . H26 H 0.4565 -0.2381 0.0095 0.046 Uiso 1 1 calc R . . C27 C 0.7150(7) 0.3102(5) 0.6268(5) 0.0486(14) Uani 1 1 d . . . C28 C 0.2721(8) 0.3724(7) 0.1616(9) 0.078(3) Uani 1 1 d . . . N1 N 0.0893(4) 0.2760(4) 0.5040(3) 0.0340(8) Uani 1 1 d . . . N2 N 0.2264(4) 0.1540(4) 0.4045(3) 0.0325(8) Uani 1 1 d . . . N3 N 0.0994(4) 0.0888(3) 0.3897(3) 0.0280(7) Uani 1 1 d . . . H3N H 0.0568 0.1166 0.4239 0.034 Uiso 1 1 calc R . . N4 N 0.6807(4) 0.0125(4) 0.1147(3) 0.0330(8) Uani 1 1 d . . . N5 N 0.4944(4) 0.0348(3) 0.2160(3) 0.0315(8) Uani 1 1 d . . . N6 N 0.4510(3) -0.0663(3) 0.1383(3) 0.0256(7) Uani 1 1 d . . . H6N H 0.5022 -0.0798 0.1061 0.031 Uiso 1 1 calc R . . O1 O 0.0996(4) -0.0591(3) 0.2723(3) 0.0388(8) Uani 1 1 d . . . O2 O 0.2516(3) -0.1230(3) 0.1519(3) 0.0385(8) Uani 1 1 d . . . O3 O 0.5234(4) 0.1683(3) 0.4522(3) 0.0393(8) Uani 1 1 d . . . O4 O 0.7435(4) 0.1415(4) 0.5098(3) 0.0501(10) Uani 1 1 d . . . O5 O 0.6052(4) 0.0914(3) 0.6071(3) 0.0426(8) Uani 1 1 d . . . O6 O 0.2547(5) 0.1633(4) 0.1783(5) 0.0608(13) Uani 1 1 d . . . O7 O 0.4537(8) 0.3129(9) 0.2847(7) 0.158(5) Uani 1 1 d . . . O8 O 0.3914(8) 0.2595(5) 0.0910(6) 0.098(2) Uani 1 1 d . . . F1 F 0.7546(5) 0.3883(3) 0.5778(4) 0.0719(12) Uani 1 1 d . . . F2 F 0.8246(5) 0.3190(4) 0.7117(3) 0.0747(13) Uani 1 1 d . . . F3 F 0.6283(5) 0.3384(4) 0.6587(5) 0.0878(16) Uani 1 1 d . . . F4 F 0.3521(6) 0.4724(4) 0.1583(6) 0.108(2) Uani 1 1 d . . . F5 F 0.1644(7) 0.3376(8) 0.0743(9) 0.193(6) Uani 1 1 d . . . F6 F 0.2283(8) 0.3900(5) 0.2391(7) 0.127(3) Uani 1 1 d . . . S1 S 0.64038(12) 0.16181(11) 0.53922(9) 0.0324(3) Uani 1 1 d . . . S2 S 0.35423(17) 0.26453(16) 0.17970(16) 0.0563(4) Uani 1 1 d . . . Ca1 Ca 0.32322(10) 0.04225(10) 0.29756(7) 0.0341(3) Uani 1 1 d . . . 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 0.042(3) 0.044(3) 0.042(3) 0.005(2) 0.023(2) 0.020(2) C2 0.064(4) 0.043(3) 0.046(3) 0.007(2) 0.027(3) 0.031(3) C3 0.061(4) 0.032(3) 0.045(3) -0.003(2) 0.013(3) 0.016(2) C4 0.040(3) 0.037(3) 0.048(3) 0.010(2) 0.015(2) 0.010(2) C5 0.035(2) 0.036(2) 0.026(2) 0.0079(18) 0.0124(18) 0.0168(19) C6 0.029(2) 0.043(3) 0.033(2) 0.0064(19) 0.0143(18) 0.0137(19) C7 0.033(2) 0.034(2) 0.0207(18) 0.0066(16) 0.0088(16) 0.0187(18) C8 0.035(2) 0.033(2) 0.028(2) 0.0137(18) 0.0106(18) 0.0186(18) C9 0.043(3) 0.039(3) 0.040(3) 0.006(2) 0.016(2) 0.020(2) C10 0.046(3) 0.033(3) 0.047(3) 0.003(2) 0.013(2) 0.013(2) C11 0.034(2) 0.038(3) 0.043(3) 0.017(2) 0.012(2) 0.010(2) C12 0.040(2) 0.043(3) 0.034(2) 0.018(2) 0.015(2) 0.020(2) C13 0.037(2) 0.035(2) 0.026(2) 0.0099(18) 0.0096(18) 0.0158(19) C14 0.042(3) 0.060(3) 0.038(3) 0.024(2) 0.023(2) 0.028(2) C15 0.031(2) 0.079(4) 0.052(3) 0.043(3) 0.024(2) 0.025(3) C16 0.034(3) 0.059(4) 0.050(3) 0.031(3) 0.010(2) 0.005(2) C17 0.045(3) 0.042(3) 0.041(3) 0.019(2) 0.010(2) 0.011(2) C18 0.032(2) 0.037(2) 0.036(2) 0.0194(19) 0.0148(19) 0.0164(19) C19 0.038(2) 0.034(2) 0.032(2) 0.0074(18) 0.0137(19) 0.0131(19) C20 0.031(2) 0.030(2) 0.0222(19) 0.0035(16) 0.0097(16) 0.0121(17) C21 0.039(2) 0.024(2) 0.0213(19) 0.0023(16) 0.0042(17) 0.0089(17) C22 0.048(3) 0.034(2) 0.034(2) 0.0068(19) 0.021(2) 0.014(2) C23 0.050(3) 0.031(2) 0.040(3) 0.005(2) 0.019(2) 0.002(2) C24 0.059(3) 0.030(2) 0.037(3) -0.001(2) 0.018(2) 0.011(2) C25 0.051(3) 0.040(3) 0.049(3) 0.001(2) 0.022(3) 0.015(2) C26 0.036(2) 0.036(3) 0.038(3) 0.004(2) 0.012(2) 0.009(2) C27 0.058(3) 0.040(3) 0.046(3) 0.000(2) 0.031(3) 0.006(2) C28 0.059(4) 0.050(4) 0.148(9) 0.050(5) 0.052(5) 0.027(3) N1 0.0339(19) 0.036(2) 0.0304(19) 0.0006(16) 0.0131(16) 0.0136(16) N2 0.0292(18) 0.042(2) 0.0302(19) 0.0072(16) 0.0141(15) 0.0166(16) N3 0.0279(17) 0.036(2) 0.0215(16) 0.0011(14) 0.0106(14) 0.0152(15) N4 0.0284(18) 0.039(2) 0.038(2) 0.0182(17) 0.0159(16) 0.0151(16) N5 0.0319(18) 0.0300(19) 0.0287(19) 0.0013(15) 0.0095(15) 0.0118(15) N6 0.0228(15) 0.0303(18) 0.0228(16) 0.0018(13) 0.0101(13) 0.0092(14) O1 0.0430(19) 0.045(2) 0.0310(17) -0.0001(15) 0.0161(15) 0.0224(16) O2 0.0289(16) 0.047(2) 0.0415(19) 0.0070(16) 0.0185(15) 0.0114(15) O3 0.0376(18) 0.0388(19) 0.0376(19) 0.0099(15) 0.0107(15) 0.0137(15) O4 0.043(2) 0.062(3) 0.046(2) -0.0015(19) 0.0210(18) 0.0234(19) O5 0.043(2) 0.041(2) 0.0351(19) 0.0106(15) 0.0093(16) 0.0105(16) O6 0.072(3) 0.042(2) 0.103(4) 0.039(2) 0.063(3) 0.025(2) O7 0.090(5) 0.157(8) 0.122(7) 0.056(6) -0.047(5) 0.000(5) O8 0.136(6) 0.066(4) 0.149(6) 0.030(4) 0.120(5) 0.036(4) F1 0.101(3) 0.0362(19) 0.086(3) 0.0173(19) 0.054(3) 0.011(2) F2 0.074(3) 0.058(2) 0.052(2) -0.0099(19) 0.011(2) -0.009(2) F3 0.095(3) 0.063(3) 0.113(4) -0.017(3) 0.071(3) 0.018(2) F4 0.115(4) 0.040(2) 0.202(7) 0.053(3) 0.094(5) 0.026(3) F5 0.074(4) 0.171(8) 0.268(12) 0.149(8) -0.022(5) 0.027(4) F6 0.158(6) 0.073(3) 0.237(9) 0.049(4) 0.164(7) 0.056(4) S1 0.0311(5) 0.0336(6) 0.0313(6) 0.0040(4) 0.0131(4) 0.0111(4) S2 0.0487(8) 0.0557(9) 0.0847(12) 0.0342(9) 0.0395(8) 0.0242(7) Ca1 0.0354(5) 0.0533(6) 0.0252(4) 0.0099(4) 0.0158(4) 0.0286(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.340(6) . ? C1 C2 1.380(8) . ? C1 H1 0.9500 . ? C2 C3 1.360(9) . ? C2 H2 0.9500 . ? C3 C4 1.377(8) . ? C3 H3 0.9500 . ? C4 C5 1.385(7) . ? C4 H4 0.9500 . ? C5 N1 1.358(6) . ? C5 C6 1.475(6) . ? C6 N2 1.274(7) . ? C6 H6 0.9500 . ? C7 O1 1.237(5) . ? C7 N3 1.355(6) . ? C7 C8 1.492(7) . ? C7 Ca1 3.216(5) . ? C8 C13 1.394(7) . ? C8 C9 1.395(7) . ? C9 C10 1.390(8) . ? C9 H9 0.9500 . ? C10 C11 1.383(8) . ? C10 H10 0.9500 . ? C11 C12 1.372(8) . ? C11 H11 0.9500 . ? C12 C13 1.387(7) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 N4 1.349(6) . ? C14 C15 1.393(8) . ? C14 H14 0.9500 . ? C15 C16 1.361(10) . ? C15 H15 0.9500 . ? C16 C17 1.358(9) . ? C16 H16 0.9500 . ? C17 C18 1.399(7) . ? C17 H17 0.9500 . ? C18 N4 1.351(7) . ? C18 C19 1.468(7) . ? C19 N5 1.270(6) . ? C19 H19 0.9500 . ? C20 O2 1.237(5) . ? C20 N6 1.352(6) . ? C20 C21 1.490(6) . ? C20 Ca1 3.224(4) . ? C21 C26 1.377(7) . ? C21 C22 1.413(7) . ? C22 C23 1.388(7) . ? C22 H22 0.9500 . ? C23 C24 1.379(8) . ? C23 H23 0.9500 . ? C24 C25 1.377(8) . ? C24 H24 0.9500 . ? C25 C26 1.379(8) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 F3 1.307(7) . ? C27 F1 1.317(7) . ? C27 F2 1.323(8) . ? C27 S1 1.819(6) . ? C28 F5 1.279(12) . ? C28 F4 1.327(8) . ? C28 F6 1.351(11) . ? C28 S2 1.781(7) . ? N2 N3 1.365(5) . ? N2 Ca1 2.575(4) . ? N3 H3N 0.8800 . ? N5 N6 1.362(5) . ? N5 Ca1 2.577(4) . ? N6 H6N 0.8800 . ? O1 Ca1 2.362(4) . ? O2 Ca1 2.375(4) . ? O3 S1 1.452(4) . ? O3 Ca1 2.410(4) . ? O4 S1 1.427(4) . ? O5 S1 1.444(4) . ? O5 Ca1 2.345(4) 2_656 ? O6 S2 1.423(4) . ? O6 Ca1 2.407(5) . ? O7 S2 1.399(8) . ? O8 S2 1.437(6) . ? S2 Ca1 3.3435(19) . ? Ca1 O5 2.345(4) 2_656 ? 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 122.5(5) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C3 C2 C1 119.6(5) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C3 C4 119.4(5) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C3 C4 C5 118.7(5) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? N1 C5 C4 122.2(4) . . ? N1 C5 C6 119.1(4) . . ? C4 C5 C6 118.7(5) . . ? N2 C6 C5 129.0(4) . . ? N2 C6 H6 115.5 . . ? C5 C6 H6 115.5 . . ? O1 C7 N3 121.0(4) . . ? O1 C7 C8 121.1(4) . . ? N3 C7 C8 117.9(4) . . ? N3 C7 Ca1 83.4(3) . . ? C8 C7 Ca1 158.7(3) . . ? C13 C8 C9 119.7(5) . . ? C13 C8 C7 122.4(4) . . ? C9 C8 C7 117.9(4) . . ? C10 C9 C8 119.7(5) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C11 C10 C9 119.8(5) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C12 C11 C10 120.8(5) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C13 120.1(5) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C12 C13 C8 119.9(5) . . ? C12 C13 H13 120.1 . . ? C8 C13 H13 120.1 . . ? N4 C14 C15 121.8(6) . . ? N4 C14 H14 119.1 . . ? C15 C14 H14 119.1 . . ? C16 C15 C14 119.9(5) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C17 C16 C15 119.4(5) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C16 C17 C18 119.1(6) . . ? C16 C17 H17 120.4 . . ? C18 C17 H17 120.4 . . ? N4 C18 C17 122.3(5) . . ? N4 C18 C19 120.2(4) . . ? C17 C18 C19 117.5(5) . . ? N5 C19 C18 129.6(5) . . ? N5 C19 H19 115.2 . . ? C18 C19 H19 115.2 . . ? O2 C20 N6 120.9(4) . . ? O2 C20 C21 121.1(4) . . ? N6 C20 C21 118.1(4) . . ? N6 C20 Ca1 83.3(2) . . ? C21 C20 Ca1 157.9(3) . . ? C26 C21 C22 119.8(4) . . ? C26 C21 C20 123.3(4) . . ? C22 C21 C20 116.9(4) . . ? C23 C22 C21 120.0(5) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C24 C23 C22 118.7(5) . . ? C24 C23 H23 120.6 . . ? C22 C23 H23 120.6 . . ? C25 C24 C23 121.4(5) . . ? C25 C24 H24 119.3 . . ? C23 C24 H24 119.3 . . ? C24 C25 C26 120.3(5) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C21 C26 C25 119.7(5) . . ? C21 C26 H26 120.2 . . ? C25 C26 H26 120.2 . . ? F3 C27 F1 108.6(6) . . ? F3 C27 F2 109.0(5) . . ? F1 C27 F2 106.4(5) . . ? F3 C27 S1 111.0(4) . . ? F1 C27 S1 111.0(4) . . ? F2 C27 S1 110.7(5) . . ? F5 C28 F4 106.9(8) . . ? F5 C28 F6 104.5(8) . . ? F4 C28 F6 111.7(8) . . ? F5 C28 S2 112.0(8) . . ? F4 C28 S2 111.6(5) . . ? F6 C28 S2 109.9(6) . . ? C1 N1 C5 117.6(4) . . ? C6 N2 N3 118.7(4) . . ? C6 N2 Ca1 128.7(3) . . ? N3 N2 Ca1 112.4(3) . . ? C7 N3 N2 118.3(4) . . ? C7 N3 H3N 120.9 . . ? N2 N3 H3N 120.9 . . ? C14 N4 C18 117.5(4) . . ? C19 N5 N6 118.1(4) . . ? C19 N5 Ca1 129.2(3) . . ? N6 N5 Ca1 112.7(3) . . ? C20 N6 N5 118.3(4) . . ? C20 N6 H6N 120.8 . . ? N5 N6 H6N 120.8 . . ? C7 O1 Ca1 123.6(3) . . ? C20 O2 Ca1 123.2(3) . . ? S1 O3 Ca1 140.5(2) . . ? S1 O5 Ca1 140.1(3) . 2_656 ? S2 O6 Ca1 119.4(3) . . ? O4 S1 O5 115.1(3) . . ? O4 S1 O3 115.0(2) . . ? O5 S1 O3 113.6(2) . . ? O4 S1 C27 105.8(3) . . ? O5 S1 C27 102.2(3) . . ? O3 S1 C27 103.1(3) . . ? O7 S2 O6 108.4(5) . . ? O7 S2 O8 120.5(6) . . ? O6 S2 O8 117.9(4) . . ? O7 S2 C28 101.8(6) . . ? O6 S2 C28 104.4(3) . . ? O8 S2 C28 100.7(4) . . ? O7 S2 Ca1 75.6(4) . . ? O8 S2 Ca1 122.0(3) . . ? C28 S2 Ca1 132.2(3) . . ? O5 Ca1 O1 88.18(14) 2_656 . ? O5 Ca1 O2 80.61(14) 2_656 . ? O1 Ca1 O2 77.18(12) . . ? O5 Ca1 O6 171.38(16) 2_656 . ? O1 Ca1 O6 94.10(14) . . ? O2 Ca1 O6 91.78(16) . . ? O5 Ca1 O3 77.03(13) 2_656 . ? O1 Ca1 O3 132.95(13) . . ? O2 Ca1 O3 140.91(13) . . ? O6 Ca1 O3 107.09(16) . . ? O5 Ca1 N2 106.10(14) 2_656 . ? O1 Ca1 N2 64.58(13) . . ? O2 Ca1 N2 140.63(13) . . ? O6 Ca1 N2 82.35(15) . . ? O3 Ca1 N2 76.99(13) . . ? O5 Ca1 N5 88.20(14) 2_656 . ? O1 Ca1 N5 141.29(13) . . ? O2 Ca1 N5 64.21(12) . . ? O6 Ca1 N5 84.82(14) . . ? O3 Ca1 N5 83.33(13) . . ? N2 Ca1 N5 152.11(14) . . ? O5 Ca1 C7 93.21(13) 2_656 . ? O1 Ca1 C7 18.69(11) . . ? O2 Ca1 C7 95.76(12) . . ? O6 Ca1 C7 91.56(13) . . ? O3 Ca1 C7 116.99(12) . . ? N2 Ca1 C7 45.92(12) . . ? N5 Ca1 C7 159.44(12) . . ? O5 Ca1 C20 79.44(13) 2_656 . ? O1 Ca1 C20 95.83(12) . . ? O2 Ca1 C20 18.72(11) . . ? O6 Ca1 C20 92.05(15) . . ? O3 Ca1 C20 123.94(12) . . ? N2 Ca1 C20 158.97(13) . . ? N5 Ca1 C20 45.70(12) . . ? C7 Ca1 C20 114.46(12) . . ? O5 Ca1 S2 156.57(11) 2_656 . ? O1 Ca1 S2 115.13(10) . . ? O2 Ca1 S2 101.40(10) . . ? O6 Ca1 S2 21.76(12) . . ? O3 Ca1 S2 87.73(10) . . ? N2 Ca1 S2 87.28(10) . . ? N5 Ca1 S2 72.24(10) . . ? C7 Ca1 S2 109.66(9) . . ? C20 Ca1 S2 95.01(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -2.1(9) . . . . ? C1 C2 C3 C4 2.1(9) . . . . ? C2 C3 C4 C5 -0.5(9) . . . . ? C3 C4 C5 N1 -1.3(8) . . . . ? C3 C4 C5 C6 179.3(5) . . . . ? N1 C5 C6 N2 -1.1(8) . . . . ? C4 C5 C6 N2 178.4(5) . . . . ? O1 C7 C8 C13 176.8(4) . . . . ? N3 C7 C8 C13 -4.5(6) . . . . ? Ca1 C7 C8 C13 173.4(6) . . . . ? O1 C7 C8 C9 -4.5(6) . . . . ? N3 C7 C8 C9 174.1(4) . . . . ? Ca1 C7 C8 C9 -7.9(10) . . . . ? C13 C8 C9 C10 -0.2(7) . . . . ? C7 C8 C9 C10 -178.9(5) . . . . ? C8 C9 C10 C11 0.3(8) . . . . ? C9 C10 C11 C12 0.1(8) . . . . ? C10 C11 C12 C13 -0.5(8) . . . . ? C11 C12 C13 C8 0.6(7) . . . . ? C9 C8 C13 C12 -0.2(7) . . . . ? C7 C8 C13 C12 178.4(4) . . . . ? N4 C14 C15 C16 0.2(8) . . . . ? C14 C15 C16 C17 -0.2(8) . . . . ? C15 C16 C17 C18 0.4(8) . . . . ? C16 C17 C18 N4 -0.6(7) . . . . ? C16 C17 C18 C19 178.4(5) . . . . ? N4 C18 C19 N5 2.6(8) . . . . ? C17 C18 C19 N5 -176.3(5) . . . . ? O2 C20 C21 C26 -177.0(5) . . . . ? N6 C20 C21 C26 3.4(7) . . . . ? Ca1 C20 C21 C26 -160.9(6) . . . . ? O2 C20 C21 C22 3.1(7) . . . . ? N6 C20 C21 C22 -176.5(4) . . . . ? Ca1 C20 C21 C22 19.3(10) . . . . ? C26 C21 C22 C23 -0.2(7) . . . . ? C20 C21 C22 C23 179.7(5) . . . . ? C21 C22 C23 C24 0.8(8) . . . . ? C22 C23 C24 C25 -1.1(9) . . . . ? C23 C24 C25 C26 0.6(9) . . . . ? C22 C21 C26 C25 -0.3(8) . . . . ? C20 C21 C26 C25 179.8(5) . . . . ? C24 C25 C26 C21 0.1(9) . . . . ? C2 C1 N1 C5 0.3(8) . . . . ? C4 C5 N1 C1 1.4(7) . . . . ? C6 C5 N1 C1 -179.1(5) . . . . ? C5 C6 N2 N3 -1.4(8) . . . . ? C5 C6 N2 Ca1 173.9(4) . . . . ? O1 C7 N3 N2 -0.5(6) . . . . ? C8 C7 N3 N2 -179.1(4) . . . . ? Ca1 C7 N3 N2 1.6(4) . . . . ? C6 N2 N3 C7 173.8(4) . . . . ? Ca1 N2 N3 C7 -2.2(5) . . . . ? C15 C14 N4 C18 -0.3(7) . . . . ? C17 C18 N4 C14 0.5(7) . . . . ? C19 C18 N4 C14 -178.4(4) . . . . ? C18 C19 N5 N6 -0.9(8) . . . . ? C18 C19 N5 Ca1 178.5(4) . . . . ? O2 C20 N6 N5 4.8(6) . . . . ? C21 C20 N6 N5 -175.6(4) . . . . ? Ca1 C20 N6 N5 -1.5(3) . . . . ? C19 N5 N6 C20 -178.4(4) . . . . ? Ca1 N5 N6 C20 2.1(5) . . . . ? N3 C7 O1 Ca1 3.4(6) . . . . ? C8 C7 O1 Ca1 -178.0(3) . . . . ? N6 C20 O2 Ca1 -10.2(6) . . . . ? C21 C20 O2 Ca1 170.2(3) . . . . ? Ca1 O5 S1 O4 7.1(5) 2_656 . . . ? Ca1 O5 S1 O3 142.6(3) 2_656 . . . ? Ca1 O5 S1 C27 -107.1(4) 2_656 . . . ? Ca1 O3 S1 O4 75.2(4) . . . . ? Ca1 O3 S1 O5 -60.4(4) . . . . ? Ca1 O3 S1 C27 -170.1(3) . . . . ? F3 C27 S1 O4 179.8(5) . . . . ? F1 C27 S1 O4 58.9(6) . . . . ? F2 C27 S1 O4 -59.0(5) . . . . ? F3 C27 S1 O5 -59.3(6) . . . . ? F1 C27 S1 O5 179.7(5) . . . . ? F2 C27 S1 O5 61.8(5) . . . . ? F3 C27 S1 O3 58.7(5) . . . . ? F1 C27 S1 O3 -62.2(5) . . . . ? F2 C27 S1 O3 179.9(4) . . . . ? Ca1 O6 S2 O7 -34.0(6) . . . . ? Ca1 O6 S2 O8 107.4(5) . . . . ? Ca1 O6 S2 C28 -141.9(4) . . . . ? F5 C28 S2 O7 -171.2(8) . . . . ? F4 C28 S2 O7 69.0(9) . . . . ? F6 C28 S2 O7 -55.6(8) . . . . ? F5 C28 S2 O6 -58.5(8) . . . . ? F4 C28 S2 O6 -178.4(7) . . . . ? F6 C28 S2 O6 57.1(7) . . . . ? F5 C28 S2 O8 64.2(8) . . . . ? F4 C28 S2 O8 -55.6(9) . . . . ? F6 C28 S2 O8 179.8(7) . . . . ? F5 C28 S2 Ca1 -90.1(9) . . . . ? F4 C28 S2 Ca1 150.1(6) . . . . ? F6 C28 S2 Ca1 25.6(9) . . . . ? C7 O1 Ca1 O5 105.6(4) . . . 2_656 ? C7 O1 Ca1 O2 -173.6(4) . . . . ? C7 O1 Ca1 O6 -82.7(4) . . . . ? C7 O1 Ca1 O3 35.3(4) . . . . ? C7 O1 Ca1 N2 -3.2(3) . . . . ? C7 O1 Ca1 N5 -169.6(3) . . . . ? C7 O1 Ca1 C20 -175.2(4) . . . . ? C7 O1 Ca1 S2 -76.9(4) . . . . ? C20 O2 Ca1 O5 -84.8(4) . . . 2_656 ? C20 O2 Ca1 O1 -175.0(4) . . . . ? C20 O2 Ca1 O6 91.2(4) . . . . ? C20 O2 Ca1 O3 -29.1(5) . . . . ? C20 O2 Ca1 N2 171.2(3) . . . . ? C20 O2 Ca1 N5 7.8(4) . . . . ? C20 O2 Ca1 C7 -177.1(4) . . . . ? C20 O2 Ca1 S2 71.5(4) . . . . ? S2 O6 Ca1 O1 165.6(3) . . . . ? S2 O6 Ca1 O2 -117.1(3) . . . . ? S2 O6 Ca1 O3 28.2(3) . . . . ? S2 O6 Ca1 N2 102.0(3) . . . . ? S2 O6 Ca1 N5 -53.2(3) . . . . ? S2 O6 Ca1 C7 147.1(3) . . . . ? S2 O6 Ca1 C20 -98.4(3) . . . . ? S1 O3 Ca1 O5 14.3(4) . . . 2_656 ? S1 O3 Ca1 O1 89.3(4) . . . . ? S1 O3 Ca1 O2 -42.4(5) . . . . ? S1 O3 Ca1 O6 -157.8(4) . . . . ? S1 O3 Ca1 N2 124.5(4) . . . . ? S1 O3 Ca1 N5 -75.4(4) . . . . ? S1 O3 Ca1 C7 101.3(4) . . . . ? S1 O3 Ca1 C20 -53.2(4) . . . . ? S1 O3 Ca1 S2 -147.7(4) . . . . ? C6 N2 Ca1 O5 107.1(4) . . . 2_656 ? N3 N2 Ca1 O5 -77.4(3) . . . 2_656 ? C6 N2 Ca1 O1 -172.9(5) . . . . ? N3 N2 Ca1 O1 2.6(3) . . . . ? C6 N2 Ca1 O2 -158.1(4) . . . . ? N3 N2 Ca1 O2 17.4(4) . . . . ? C6 N2 Ca1 O6 -74.7(4) . . . . ? N3 N2 Ca1 O6 100.8(3) . . . . ? C6 N2 Ca1 O3 34.9(4) . . . . ? N3 N2 Ca1 O3 -149.6(3) . . . . ? C6 N2 Ca1 N5 -11.3(6) . . . . ? N3 N2 Ca1 N5 164.2(3) . . . . ? C6 N2 Ca1 C7 -174.4(5) . . . . ? N3 N2 Ca1 C7 1.1(2) . . . . ? C6 N2 Ca1 C20 -150.3(4) . . . . ? N3 N2 Ca1 C20 25.2(6) . . . . ? C6 N2 Ca1 S2 -53.4(4) . . . . ? N3 N2 Ca1 S2 122.1(3) . . . . ? C19 N5 Ca1 O5 -103.5(4) . . . 2_656 ? N6 N5 Ca1 O5 75.9(3) . . . 2_656 ? C19 N5 Ca1 O1 171.6(4) . . . . ? N6 N5 Ca1 O1 -8.9(4) . . . . ? C19 N5 Ca1 O2 176.0(5) . . . . ? N6 N5 Ca1 O2 -4.5(3) . . . . ? C19 N5 Ca1 O6 81.5(4) . . . . ? N6 N5 Ca1 O6 -99.0(3) . . . . ? C19 N5 Ca1 O3 -26.4(4) . . . . ? N6 N5 Ca1 O3 153.0(3) . . . . ? C19 N5 Ca1 N2 18.7(6) . . . . ? N6 N5 Ca1 N2 -161.8(3) . . . . ? C19 N5 Ca1 C7 162.1(4) . . . . ? N6 N5 Ca1 C7 -18.5(5) . . . . ? C19 N5 Ca1 C20 179.5(5) . . . . ? N6 N5 Ca1 C20 -1.1(2) . . . . ? C19 N5 Ca1 S2 63.4(4) . . . . ? N6 N5 Ca1 S2 -117.2(3) . . . . ? O1 C7 Ca1 O5 -74.6(4) . . . 2_656 ? N3 C7 Ca1 O5 108.3(3) . . . 2_656 ? C8 C7 Ca1 O5 -69.8(8) . . . 2_656 ? N3 C7 Ca1 O1 -177.0(5) . . . . ? C8 C7 Ca1 O1 4.8(7) . . . . ? O1 C7 Ca1 O2 6.3(4) . . . . ? N3 C7 Ca1 O2 -170.8(2) . . . . ? C8 C7 Ca1 O2 11.1(8) . . . . ? O1 C7 Ca1 O6 98.2(4) . . . . ? N3 C7 Ca1 O6 -78.8(3) . . . . ? C8 C7 Ca1 O6 103.0(8) . . . . ? O1 C7 Ca1 O3 -151.7(4) . . . . ? N3 C7 Ca1 O3 31.3(3) . . . . ? C8 C7 Ca1 O3 -146.9(8) . . . . ? O1 C7 Ca1 N2 176.0(4) . . . . ? N3 C7 Ca1 N2 -1.1(2) . . . . ? C8 C7 Ca1 N2 -179.2(8) . . . . ? O1 C7 Ca1 N5 18.8(6) . . . . ? N3 C7 Ca1 N5 -158.2(3) . . . . ? C8 C7 Ca1 N5 23.7(10) . . . . ? O1 C7 Ca1 C20 5.2(4) . . . . ? N3 C7 Ca1 C20 -171.8(2) . . . . ? C8 C7 Ca1 C20 10.1(8) . . . . ? O1 C7 Ca1 S2 110.6(4) . . . . ? N3 C7 Ca1 S2 -66.5(2) . . . . ? C8 C7 Ca1 S2 115.4(8) . . . . ? O2 C20 Ca1 O5 91.9(4) . . . 2_656 ? N6 C20 Ca1 O5 -96.9(3) . . . 2_656 ? C21 C20 Ca1 O5 69.1(8) . . . 2_656 ? O2 C20 Ca1 O1 4.9(4) . . . . ? N6 C20 Ca1 O1 176.1(3) . . . . ? C21 C20 Ca1 O1 -17.9(8) . . . . ? N6 C20 Ca1 O2 171.2(5) . . . . ? C21 C20 Ca1 O2 -22.8(7) . . . . ? O2 C20 Ca1 O6 -89.5(4) . . . . ? N6 C20 Ca1 O6 81.7(3) . . . . ? C21 C20 Ca1 O6 -112.2(8) . . . . ? O2 C20 Ca1 O3 158.3(4) . . . . ? N6 C20 Ca1 O3 -30.5(3) . . . . ? C21 C20 Ca1 O3 135.5(8) . . . . ? O2 C20 Ca1 N2 -15.6(6) . . . . ? N6 C20 Ca1 N2 155.6(3) . . . . ? C21 C20 Ca1 N2 -38.4(10) . . . . ? O2 C20 Ca1 N5 -170.2(4) . . . . ? N6 C20 Ca1 N5 1.0(2) . . . . ? C21 C20 Ca1 N5 167.0(9) . . . . ? O2 C20 Ca1 C7 3.2(4) . . . . ? N6 C20 Ca1 C7 174.4(2) . . . . ? C21 C20 Ca1 C7 -19.6(8) . . . . ? O2 C20 Ca1 S2 -111.1(4) . . . . ? N6 C20 Ca1 S2 60.1(2) . . . . ? C21 C20 Ca1 S2 -133.9(8) . . . . ? O7 S2 Ca1 O5 -55.4(6) . . . 2_656 ? O6 S2 Ca1 O5 157.9(4) . . . 2_656 ? O8 S2 Ca1 O5 61.9(5) . . . 2_656 ? C28 S2 Ca1 O5 -148.3(5) . . . 2_656 ? O7 S2 Ca1 O1 130.9(6) . . . . ? O6 S2 Ca1 O1 -15.9(3) . . . . ? O8 S2 Ca1 O1 -111.8(4) . . . . ? C28 S2 Ca1 O1 37.9(5) . . . . ? O7 S2 Ca1 O2 -148.0(6) . . . . ? O6 S2 Ca1 O2 65.2(3) . . . . ? O8 S2 Ca1 O2 -30.8(4) . . . . ? C28 S2 Ca1 O2 119.0(5) . . . . ? O7 S2 Ca1 O6 146.8(6) . . . . ? O8 S2 Ca1 O6 -95.9(5) . . . . ? C28 S2 Ca1 O6 53.8(6) . . . . ? O7 S2 Ca1 O3 -6.4(6) . . . . ? O6 S2 Ca1 O3 -153.2(3) . . . . ? O8 S2 Ca1 O3 110.9(4) . . . . ? C28 S2 Ca1 O3 -99.3(5) . . . . ? O7 S2 Ca1 N2 70.7(6) . . . . ? O6 S2 Ca1 N2 -76.1(3) . . . . ? O8 S2 Ca1 N2 -172.0(4) . . . . ? C28 S2 Ca1 N2 -22.2(5) . . . . ? O7 S2 Ca1 N5 -90.1(6) . . . . ? O6 S2 Ca1 N5 123.1(3) . . . . ? O8 S2 Ca1 N5 27.2(4) . . . . ? C28 S2 Ca1 N5 177.0(5) . . . . ? O7 S2 Ca1 C7 111.5(6) . . . . ? O6 S2 Ca1 C7 -35.2(3) . . . . ? O8 S2 Ca1 C7 -131.2(4) . . . . ? C28 S2 Ca1 C7 18.6(5) . . . . ? O7 S2 Ca1 C20 -130.3(6) . . . . ? O6 S2 Ca1 C20 83.0(3) . . . . ? O8 S2 Ca1 C20 -13.0(4) . . . . ? C28 S2 Ca1 C20 136.8(5) . . . . ? 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 H3N N1 0.88 1.97 2.644(5) 132.6 . N6 H6N N4 0.88 1.98 2.665(5) 133.9 . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 29.06 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 3.796 _refine_diff_density_min -2.068 _refine_diff_density_rms 0.140 _database_code_depnum_ccdc_archive 'CCDC 971152' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_jmlgv130515 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H20 Ca Cl2 N8, C4 H10 O' _chemical_formula_sum 'C26 H30 Ca Cl2 N8 O' _chemical_formula_weight 581.56 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.9231(9) _cell_length_b 13.4981(9) _cell_length_c 15.7366(7) _cell_angle_alpha 90.00 _cell_angle_beta 104.682(3) _cell_angle_gamma 90.00 _cell_volume 2860.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 56784 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.441 _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 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _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_reflns_number 24357 _diffrn_reflns_av_R_equivalents 0.0662 _diffrn_reflns_av_sigmaI/netI 0.0651 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6550 _reflns_number_gt 3666 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^ > 2\s(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^)+(0.0967P)^2^+0.9133P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6550 _refine_ls_number_parameters 353 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1228 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1910 _refine_ls_wR_factor_gt 0.1499 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.001 _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 0.0467(2) 0.3968(3) 0.9256(2) 0.0455(8) Uani 1 1 d . . . H1 H 0.0321 0.3756 0.9786 0.055 Uiso 1 1 calc R . . C2 C -0.0210(3) 0.4570(3) 0.8708(2) 0.0594(11) Uani 1 1 d . . . H2 H -0.0806 0.4768 0.8850 0.071 Uiso 1 1 calc R . . C3 C 0.0013(3) 0.4879(3) 0.7934(2) 0.0647(12) Uani 1 1 d . . . H3 H -0.0441 0.5287 0.7530 0.078 Uiso 1 1 calc R . . C4 C 0.0874(3) 0.4599(3) 0.7760(2) 0.0565(10) Uani 1 1 d . . . H4 H 0.1038 0.4816 0.7240 0.068 Uiso 1 1 calc R . . C5 C 0.1512(2) 0.3990(3) 0.83532(19) 0.0423(8) Uani 1 1 d . . . C6 C 0.3817(2) 0.2831(2) 0.85124(18) 0.0364(8) Uani 1 1 d . . . H6 H 0.3933 0.3040 0.7970 0.044 Uiso 1 1 calc R . . C7 C 0.4518(2) 0.2190(3) 0.9096(2) 0.0395(8) Uani 1 1 d . . . C8 C 0.5385(3) 0.1884(3) 0.8861(2) 0.0539(10) Uani 1 1 d . . . H8 H 0.5510 0.2093 0.8322 0.065 Uiso 1 1 calc R . . C9 C 0.6046(3) 0.1276(3) 0.9426(3) 0.0647(12) Uani 1 1 d . . . H9 H 0.6631 0.1051 0.9281 0.078 Uiso 1 1 calc R . . C10 C 0.5846(3) 0.1003(3) 1.0202(3) 0.0597(11) Uani 1 1 d . . . H10 H 0.6295 0.0592 1.0607 0.072 Uiso 1 1 calc R . . C11 C 0.4979(2) 0.1334(3) 1.0386(2) 0.0490(9) Uani 1 1 d . . . H11 H 0.4848 0.1138 1.0925 0.059 Uiso 1 1 calc R . . C12 C 0.4305(2) 0.4113(3) 1.0763(2) 0.0436(8) Uani 1 1 d . . . H12 H 0.4473 0.3930 1.0236 0.052 Uiso 1 1 calc R . . C13 C 0.4910(3) 0.4764(3) 1.1309(2) 0.0524(10) Uani 1 1 d . . . H13 H 0.5479 0.5031 1.1163 0.063 Uiso 1 1 calc R . . C14 C 0.4675(3) 0.5029(3) 1.2083(2) 0.0533(10) Uani 1 1 d . . . H14 H 0.5094 0.5468 1.2483 0.064 Uiso 1 1 calc R . . C15 C 0.3852(3) 0.4661(3) 1.2264(2) 0.0459(9) Uani 1 1 d . . . H15 H 0.3675 0.4842 1.2788 0.055 Uiso 1 1 calc R . . C16 C 0.3263(2) 0.4005(2) 1.16625(18) 0.0350(7) Uani 1 1 d . . . C17 C 0.1034(2) 0.2695(3) 1.14444(19) 0.0384(8) Uani 1 1 d . . . H17 H 0.0890 0.2862 1.1985 0.046 Uiso 1 1 calc R . . C18 C 0.0376(2) 0.2056(2) 1.0824(2) 0.0375(8) Uani 1 1 d . . . C19 C -0.0540(2) 0.1770(3) 1.0971(2) 0.0495(9) Uani 1 1 d . . . H19 H -0.0719 0.1973 1.1489 0.059 Uiso 1 1 calc R . . C20 C -0.1173(3) 0.1192(3) 1.0354(3) 0.0570(10) Uani 1 1 d . . . H20 H -0.1788 0.0979 1.0447 0.068 Uiso 1 1 calc R . . C21 C -0.0908(2) 0.0928(3) 0.9605(3) 0.0527(10) Uani 1 1 d . . . H21 H -0.1340 0.0544 0.9163 0.063 Uiso 1 1 calc R . . C22 C 0.0014(2) 0.1240(3) 0.9508(2) 0.0460(9) Uani 1 1 d . . . H22 H 0.0200 0.1052 0.8990 0.055 Uiso 1 1 calc R . . C23 C 0.7644(4) 0.2191(5) 0.2654(3) 0.116(2) Uani 1 1 d . . . H23A H 0.7657 0.1558 0.2353 0.174 Uiso 1 1 calc R . . H23B H 0.7297 0.2107 0.3119 0.174 Uiso 1 1 calc R . . H23C H 0.8326 0.2413 0.2913 0.174 Uiso 1 1 calc R . . C24 C 0.7118(4) 0.2941(5) 0.2014(3) 0.0895(16) Uani 1 1 d . . . H24A H 0.6427 0.2722 0.1755 0.107 Uiso 1 1 calc R . . H24B H 0.7094 0.3579 0.2318 0.107 Uiso 1 1 calc R . . C25 C 0.7148(3) 0.3715(4) 0.0665(3) 0.0776(13) Uani 1 1 d . . . H25A H 0.7060 0.4370 0.0917 0.093 Uiso 1 1 calc R . . H25B H 0.6482 0.3453 0.0373 0.093 Uiso 1 1 calc R . . C26 C 0.7727(3) 0.3831(4) 0.0013(3) 0.0772(13) Uani 1 1 d . . . H26A H 0.8414 0.3999 0.0311 0.116 Uiso 1 1 calc R . . H26B H 0.7439 0.4362 -0.0397 0.116 Uiso 1 1 calc R . . H26C H 0.7715 0.3210 -0.0312 0.116 Uiso 1 1 calc R . . N1 N 0.13230(18) 0.3655(2) 0.90978(15) 0.0383(6) Uani 1 1 d . . . N2 N 0.2400(2) 0.3701(2) 0.81738(17) 0.0439(7) Uani 1 1 d . . . N3 N 0.30318(18) 0.3116(2) 0.87375(14) 0.0340(6) Uani 1 1 d . . . N4 N 0.43178(18) 0.1913(2) 0.98477(16) 0.0375(6) Uani 1 1 d . . . N5 N 0.34867(18) 0.37136(19) 1.09234(15) 0.0344(6) Uani 1 1 d . . . N6 N 0.2417(2) 0.3641(2) 1.18408(16) 0.0411(7) Uani 1 1 d . . . N7 N 0.18209(17) 0.30350(19) 1.12555(14) 0.0322(6) Uani 1 1 d . . . N8 N 0.06520(17) 0.1787(2) 1.01040(16) 0.0369(6) Uani 1 1 d . . . O1 O 0.7614(2) 0.3072(2) 0.13402(17) 0.0727(8) Uani 1 1 d . . . Cl1 Cl 0.20842(5) 0.08800(6) 0.87069(4) 0.0363(2) Uani 1 1 d . . . Cl2 Cl 0.30193(6) 0.09345(7) 1.13682(4) 0.0424(2) Uani 1 1 d . . . Ca1 Ca 0.24720(4) 0.22947(5) 1.00095(3) 0.02714(18) Uani 1 1 d . . . H2N H 0.254(2) 0.384(2) 0.763(2) 0.043(9) Uiso 1 1 d . . . H6N H 0.230(2) 0.377(2) 1.236(2) 0.042(9) Uiso 1 1 d . . . 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 0.049(2) 0.043(2) 0.0428(18) 0.0070(16) 0.0078(15) 0.0082(17) C2 0.050(2) 0.060(3) 0.061(2) 0.000(2) -0.0001(18) 0.015(2) C3 0.075(3) 0.061(3) 0.044(2) 0.0111(19) -0.0125(19) 0.019(2) C4 0.064(3) 0.061(3) 0.0366(18) 0.0112(17) -0.0005(17) 0.010(2) C5 0.055(2) 0.038(2) 0.0264(16) 0.0014(14) -0.0033(14) -0.0038(17) C6 0.0402(18) 0.045(2) 0.0305(15) -0.0075(14) 0.0203(13) -0.0126(15) C7 0.0340(17) 0.044(2) 0.0435(18) -0.0161(16) 0.0155(14) -0.0101(15) C8 0.045(2) 0.065(3) 0.062(2) -0.024(2) 0.0310(18) -0.015(2) C9 0.040(2) 0.060(3) 0.100(3) -0.022(2) 0.028(2) 0.004(2) C10 0.0353(19) 0.062(3) 0.082(3) -0.003(2) 0.0164(18) 0.0067(18) C11 0.0303(17) 0.053(2) 0.062(2) -0.0041(19) 0.0084(15) 0.0054(17) C12 0.048(2) 0.044(2) 0.0394(18) -0.0072(16) 0.0137(15) -0.0063(17) C13 0.048(2) 0.058(3) 0.052(2) -0.0042(19) 0.0150(16) -0.0162(19) C14 0.060(2) 0.055(3) 0.0405(19) -0.0131(17) 0.0041(16) -0.017(2) C15 0.055(2) 0.050(2) 0.0314(16) -0.0065(15) 0.0083(15) -0.0047(18) C16 0.0396(17) 0.034(2) 0.0285(15) 0.0003(13) 0.0042(13) 0.0026(15) C17 0.0413(18) 0.047(2) 0.0327(16) 0.0089(15) 0.0201(14) 0.0112(16) C18 0.0321(16) 0.040(2) 0.0440(18) 0.0113(15) 0.0162(14) 0.0063(15) C19 0.0392(19) 0.057(3) 0.058(2) 0.0190(19) 0.0237(16) 0.0083(18) C20 0.0324(18) 0.056(3) 0.083(3) 0.021(2) 0.0154(18) -0.0065(18) C21 0.0309(18) 0.046(2) 0.078(3) 0.0027(19) 0.0078(17) -0.0049(16) C22 0.0321(17) 0.049(2) 0.057(2) -0.0023(17) 0.0109(15) -0.0021(16) C23 0.110(4) 0.165(6) 0.082(4) 0.028(4) 0.042(3) 0.006(4) C24 0.078(3) 0.119(5) 0.080(3) 0.005(3) 0.037(3) 0.005(3) C25 0.072(3) 0.070(3) 0.083(3) -0.006(3) 0.007(2) 0.009(3) C26 0.095(3) 0.062(3) 0.081(3) 0.014(2) 0.033(3) 0.010(3) N1 0.0396(15) 0.0408(18) 0.0312(13) 0.0043(12) 0.0027(11) 0.0042(13) N2 0.0507(17) 0.053(2) 0.0299(14) 0.0077(13) 0.0135(12) 0.0019(15) N3 0.0392(14) 0.0373(17) 0.0252(12) -0.0023(11) 0.0074(10) -0.0072(12) N4 0.0318(14) 0.0424(18) 0.0405(14) -0.0092(12) 0.0131(11) -0.0040(12) N5 0.0372(14) 0.0372(17) 0.0286(13) -0.0033(11) 0.0082(10) -0.0033(12) N6 0.0460(16) 0.053(2) 0.0261(14) -0.0073(13) 0.0122(12) -0.0009(14) N7 0.0363(14) 0.0358(16) 0.0262(12) 0.0024(11) 0.0108(10) 0.0071(12) N8 0.0305(13) 0.0404(17) 0.0403(14) 0.0010(12) 0.0099(11) 0.0019(12) O1 0.0683(18) 0.084(2) 0.0697(18) 0.0056(16) 0.0238(14) 0.0117(17) Cl1 0.0401(4) 0.0426(5) 0.0278(4) -0.0049(3) 0.0116(3) -0.0100(4) Cl2 0.0510(5) 0.0513(6) 0.0279(4) 0.0066(3) 0.0155(3) 0.0191(4) Ca1 0.0267(3) 0.0340(4) 0.0214(3) 0.0000(2) 0.0073(2) 0.0005(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.346(4) . ? C1 C2 1.371(5) . ? C1 H1 0.9500 . ? C2 C3 1.395(5) . ? C2 H2 0.9500 . ? C3 C4 1.350(5) . ? C3 H3 0.9500 . ? C4 C5 1.385(5) . ? C4 H4 0.9500 . ? C5 N1 1.342(4) . ? C5 N2 1.391(4) . ? C6 N3 1.290(4) . ? C6 C7 1.446(5) . ? C6 H6 0.9500 . ? C7 N4 1.336(4) . ? C7 C8 1.410(4) . ? C8 C9 1.377(6) . ? C8 H8 0.9500 . ? C9 C10 1.369(6) . ? C9 H9 0.9500 . ? C10 C11 1.385(4) . ? C10 H10 0.9500 . ? C11 N4 1.334(4) . ? C11 H11 0.9500 . ? C12 N5 1.341(4) . ? C12 C13 1.362(5) . ? C12 H12 0.9500 . ? C13 C14 1.384(5) . ? C13 H13 0.9500 . ? C14 C15 1.344(5) . ? C14 H14 0.9500 . ? C15 C16 1.400(4) . ? C15 H15 0.9500 . ? C16 N5 1.337(4) . ? C16 N6 1.370(4) . ? C17 N7 1.291(4) . ? C17 C18 1.443(5) . ? C17 H17 0.9500 . ? C18 N8 1.336(4) . ? C18 C19 1.406(4) . ? C19 C20 1.376(5) . ? C19 H19 0.9500 . ? C20 C21 1.369(5) . ? C20 H20 0.9500 . ? C21 C22 1.396(4) . ? C21 H21 0.9500 . ? C22 N8 1.339(4) . ? C22 H22 0.9500 . ? C23 C24 1.484(8) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 O1 1.415(5) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 O1 1.398(5) . ? C25 C26 1.465(5) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? N1 Ca1 2.613(3) . ? N2 N3 1.337(4) . ? N2 H2N 0.95(3) . ? N3 Ca1 2.576(2) . ? N4 Ca1 2.696(2) . ? N5 Ca1 2.589(3) . ? N6 N7 1.348(4) . ? N6 H6N 0.90(3) . ? N7 Ca1 2.562(2) . ? N8 Ca1 2.665(2) . ? Cl1 Ca1 2.7529(9) . ? Cl2 Ca1 2.7744(9) . ? 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 124.7(3) . . ? N1 C1 H1 117.6 . . ? C2 C1 H1 117.6 . . ? C1 C2 C3 117.2(4) . . ? C1 C2 H2 121.4 . . ? C3 C2 H2 121.4 . . ? C4 C3 C2 120.0(3) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 118.7(3) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? N1 C5 C4 123.6(3) . . ? N1 C5 N2 117.6(3) . . ? C4 C5 N2 118.7(3) . . ? N3 C6 C7 119.1(3) . . ? N3 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? N4 C7 C8 122.3(3) . . ? N4 C7 C6 118.1(3) . . ? C8 C7 C6 119.6(3) . . ? C9 C8 C7 118.8(3) . . ? C9 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? C10 C9 C8 118.9(3) . . ? C10 C9 H9 120.6 . . ? C8 C9 H9 120.6 . . ? C9 C10 C11 119.0(4) . . ? C9 C10 H10 120.5 . . ? C11 C10 H10 120.5 . . ? N4 C11 C10 123.7(3) . . ? N4 C11 H11 118.2 . . ? C10 C11 H11 118.2 . . ? N5 C12 C13 124.0(3) . . ? N5 C12 H12 118.0 . . ? C13 C12 H12 118.0 . . ? C12 C13 C14 118.4(3) . . ? C12 C13 H13 120.8 . . ? C14 C13 H13 120.8 . . ? C15 C14 C13 119.7(3) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 118.3(3) . . ? C14 C15 H15 120.8 . . ? C16 C15 H15 120.8 . . ? N5 C16 N6 118.3(3) . . ? N5 C16 C15 123.3(3) . . ? N6 C16 C15 118.4(3) . . ? N7 C17 C18 119.2(3) . . ? N7 C17 H17 120.4 . . ? C18 C17 H17 120.4 . . ? N8 C18 C19 122.2(3) . . ? N8 C18 C17 117.8(3) . . ? C19 C18 C17 120.0(3) . . ? C20 C19 C18 119.0(3) . . ? C20 C19 H19 120.5 . . ? C18 C19 H19 120.5 . . ? C21 C20 C19 119.4(3) . . ? C21 C20 H20 120.3 . . ? C19 C20 H20 120.3 . . ? C20 C21 C22 118.2(3) . . ? C20 C21 H21 120.9 . . ? C22 C21 H21 120.9 . . ? N8 C22 C21 123.7(3) . . ? N8 C22 H22 118.2 . . ? C21 C22 H22 118.2 . . ? C24 C23 H23A 109.5 . . ? C24 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C24 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O1 C24 C23 110.1(4) . . ? O1 C24 H24A 109.6 . . ? C23 C24 H24A 109.6 . . ? O1 C24 H24B 109.6 . . ? C23 C24 H24B 109.6 . . ? H24A C24 H24B 108.2 . . ? O1 C25 C26 111.6(4) . . ? O1 C25 H25A 109.3 . . ? C26 C25 H25A 109.3 . . ? O1 C25 H25B 109.3 . . ? C26 C25 H25B 109.3 . . ? H25A C25 H25B 108.0 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C5 N1 C1 115.8(3) . . ? C5 N1 Ca1 119.2(2) . . ? C1 N1 Ca1 124.5(2) . . ? N3 N2 C5 120.0(2) . . ? N3 N2 H2N 117.8(19) . . ? C5 N2 H2N 121.7(19) . . ? C6 N3 N2 117.0(2) . . ? C6 N3 Ca1 122.0(2) . . ? N2 N3 Ca1 119.46(18) . . ? C11 N4 C7 117.4(3) . . ? C11 N4 Ca1 125.0(2) . . ? C7 N4 Ca1 116.6(2) . . ? C16 N5 C12 116.2(3) . . ? C16 N5 Ca1 119.1(2) . . ? C12 N5 Ca1 124.23(19) . . ? N7 N6 C16 119.4(2) . . ? N7 N6 H6N 121(2) . . ? C16 N6 H6N 119(2) . . ? C17 N7 N6 118.0(2) . . ? C17 N7 Ca1 121.5(2) . . ? N6 N7 Ca1 118.91(17) . . ? C18 N8 C22 117.5(3) . . ? C18 N8 Ca1 117.4(2) . . ? C22 N8 Ca1 125.0(2) . . ? C25 O1 C24 115.2(3) . . ? N7 Ca1 N3 131.46(9) . . ? N7 Ca1 N5 62.32(8) . . ? N3 Ca1 N5 83.29(8) . . ? N7 Ca1 N1 81.95(8) . . ? N3 Ca1 N1 62.25(8) . . ? N5 Ca1 N1 87.54(9) . . ? N7 Ca1 N8 62.09(8) . . ? N3 Ca1 N8 129.29(8) . . ? N5 Ca1 N8 123.50(8) . . ? N1 Ca1 N8 75.69(8) . . ? N7 Ca1 N4 132.64(8) . . ? N3 Ca1 N4 61.67(8) . . ? N5 Ca1 N4 78.16(8) . . ? N1 Ca1 N4 123.24(8) . . ? N8 Ca1 N4 154.00(9) . . ? N7 Ca1 Cl1 143.09(6) . . ? N3 Ca1 Cl1 76.17(6) . . ? N5 Ca1 Cl1 154.58(6) . . ? N1 Ca1 Cl1 95.82(6) . . ? N8 Ca1 Cl1 81.57(6) . . ? N4 Ca1 Cl1 78.98(6) . . ? N7 Ca1 Cl2 75.51(6) . . ? N3 Ca1 Cl2 143.68(6) . . ? N5 Ca1 Cl2 93.26(6) . . ? N1 Ca1 Cl2 153.99(6) . . ? N8 Ca1 Cl2 82.31(6) . . ? N4 Ca1 Cl2 82.19(6) . . ? Cl1 Ca1 Cl2 94.50(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -0.2(6) . . . . ? C1 C2 C3 C4 -1.2(6) . . . . ? C2 C3 C4 C5 1.2(6) . . . . ? C3 C4 C5 N1 0.2(6) . . . . ? C3 C4 C5 N2 -180.0(4) . . . . ? N3 C6 C7 N4 0.4(5) . . . . ? N3 C6 C7 C8 -179.2(3) . . . . ? N4 C7 C8 C9 0.1(5) . . . . ? C6 C7 C8 C9 179.7(3) . . . . ? C7 C8 C9 C10 -0.9(6) . . . . ? C8 C9 C10 C11 0.9(6) . . . . ? C9 C10 C11 N4 -0.1(6) . . . . ? N5 C12 C13 C14 0.6(6) . . . . ? C12 C13 C14 C15 -1.7(6) . . . . ? C13 C14 C15 C16 0.9(6) . . . . ? C14 C15 C16 N5 1.2(5) . . . . ? C14 C15 C16 N6 -179.1(3) . . . . ? N7 C17 C18 N8 4.8(4) . . . . ? N7 C17 C18 C19 -172.7(3) . . . . ? N8 C18 C19 C20 0.1(5) . . . . ? C17 C18 C19 C20 177.5(3) . . . . ? C18 C19 C20 C21 -1.4(5) . . . . ? C19 C20 C21 C22 1.6(6) . . . . ? C20 C21 C22 N8 -0.4(6) . . . . ? C4 C5 N1 C1 -1.5(5) . . . . ? N2 C5 N1 C1 178.7(3) . . . . ? C4 C5 N1 Ca1 170.4(3) . . . . ? N2 C5 N1 Ca1 -9.5(4) . . . . ? C2 C1 N1 C5 1.5(5) . . . . ? C2 C1 N1 Ca1 -169.9(3) . . . . ? N1 C5 N2 N3 -0.5(5) . . . . ? C4 C5 N2 N3 179.7(3) . . . . ? C7 C6 N3 N2 -179.4(3) . . . . ? C7 C6 N3 Ca1 -13.6(4) . . . . ? C5 N2 N3 C6 176.4(3) . . . . ? C5 N2 N3 Ca1 10.3(4) . . . . ? C10 C11 N4 C7 -0.7(5) . . . . ? C10 C11 N4 Ca1 167.6(3) . . . . ? C8 C7 N4 C11 0.7(5) . . . . ? C6 C7 N4 C11 -179.0(3) . . . . ? C8 C7 N4 Ca1 -168.6(2) . . . . ? C6 C7 N4 Ca1 11.8(4) . . . . ? N6 C16 N5 C12 178.0(3) . . . . ? C15 C16 N5 C12 -2.2(5) . . . . ? N6 C16 N5 Ca1 -9.2(4) . . . . ? C15 C16 N5 Ca1 170.5(2) . . . . ? C13 C12 N5 C16 1.4(5) . . . . ? C13 C12 N5 Ca1 -171.0(3) . . . . ? N5 C16 N6 N7 -2.5(4) . . . . ? C15 C16 N6 N7 177.8(3) . . . . ? C18 C17 N7 N6 179.1(3) . . . . ? C18 C17 N7 Ca1 -15.1(4) . . . . ? C16 N6 N7 C17 179.3(3) . . . . ? C16 N6 N7 Ca1 13.1(4) . . . . ? C19 C18 N8 C22 1.1(5) . . . . ? C17 C18 N8 C22 -176.4(3) . . . . ? C19 C18 N8 Ca1 -175.5(2) . . . . ? C17 C18 N8 Ca1 7.0(4) . . . . ? C21 C22 N8 C18 -0.9(5) . . . . ? C21 C22 N8 Ca1 175.4(3) . . . . ? C26 C25 O1 C24 178.1(4) . . . . ? C23 C24 O1 C25 175.9(5) . . . . ? C17 N7 Ca1 N3 132.1(2) . . . . ? N6 N7 Ca1 N3 -62.3(2) . . . . ? C17 N7 Ca1 N5 -177.7(2) . . . . ? N6 N7 Ca1 N5 -12.01(19) . . . . ? C17 N7 Ca1 N1 90.9(2) . . . . ? N6 N7 Ca1 N1 -103.5(2) . . . . ? C17 N7 Ca1 N8 12.8(2) . . . . ? N6 N7 Ca1 N8 178.5(2) . . . . ? C17 N7 Ca1 N4 -140.7(2) . . . . ? N6 N7 Ca1 N4 25.0(3) . . . . ? C17 N7 Ca1 Cl1 1.9(3) . . . . ? N6 N7 Ca1 Cl1 167.56(16) . . . . ? C17 N7 Ca1 Cl2 -76.1(2) . . . . ? N6 N7 Ca1 Cl2 89.6(2) . . . . ? C6 N3 Ca1 N7 136.9(2) . . . . ? N2 N3 Ca1 N7 -57.7(2) . . . . ? C6 N3 Ca1 N5 93.7(2) . . . . ? N2 N3 Ca1 N5 -100.9(2) . . . . ? C6 N3 Ca1 N1 -175.6(3) . . . . ? N2 N3 Ca1 N1 -10.2(2) . . . . ? C6 N3 Ca1 N8 -137.9(2) . . . . ? N2 N3 Ca1 N8 27.5(3) . . . . ? C6 N3 Ca1 N4 13.5(2) . . . . ? N2 N3 Ca1 N4 178.9(2) . . . . ? C6 N3 Ca1 Cl1 -71.2(2) . . . . ? N2 N3 Ca1 Cl1 94.1(2) . . . . ? C6 N3 Ca1 Cl2 7.3(3) . . . . ? N2 N3 Ca1 Cl2 172.70(17) . . . . ? C16 N5 Ca1 N7 10.8(2) . . . . ? C12 N5 Ca1 N7 -177.0(3) . . . . ? C16 N5 Ca1 N3 155.4(2) . . . . ? C12 N5 Ca1 N3 -32.5(2) . . . . ? C16 N5 Ca1 N1 93.0(2) . . . . ? C12 N5 Ca1 N1 -94.8(2) . . . . ? C16 N5 Ca1 N8 22.0(2) . . . . ? C12 N5 Ca1 N8 -165.9(2) . . . . ? C16 N5 Ca1 N4 -142.2(2) . . . . ? C12 N5 Ca1 N4 29.9(2) . . . . ? C16 N5 Ca1 Cl1 -168.56(16) . . . . ? C12 N5 Ca1 Cl1 3.6(3) . . . . ? C16 N5 Ca1 Cl2 -60.9(2) . . . . ? C12 N5 Ca1 Cl2 111.2(2) . . . . ? C5 N1 Ca1 N7 156.1(2) . . . . ? C1 N1 Ca1 N7 -32.8(3) . . . . ? C5 N1 Ca1 N3 10.0(2) . . . . ? C1 N1 Ca1 N3 -178.9(3) . . . . ? C5 N1 Ca1 N5 93.7(2) . . . . ? C1 N1 Ca1 N5 -95.1(3) . . . . ? C5 N1 Ca1 N8 -140.7(2) . . . . ? C1 N1 Ca1 N8 30.4(3) . . . . ? C5 N1 Ca1 N4 19.6(3) . . . . ? C1 N1 Ca1 N4 -169.3(2) . . . . ? C5 N1 Ca1 Cl1 -61.0(2) . . . . ? C1 N1 Ca1 Cl1 110.1(3) . . . . ? C5 N1 Ca1 Cl2 -173.88(17) . . . . ? C1 N1 Ca1 Cl2 -2.8(3) . . . . ? C18 N8 Ca1 N7 -9.7(2) . . . . ? C22 N8 Ca1 N7 174.0(3) . . . . ? C18 N8 Ca1 N3 -132.0(2) . . . . ? C22 N8 Ca1 N3 51.7(3) . . . . ? C18 N8 Ca1 N5 -20.8(3) . . . . ? C22 N8 Ca1 N5 162.8(2) . . . . ? C18 N8 Ca1 N1 -98.0(2) . . . . ? C22 N8 Ca1 N1 85.7(3) . . . . ? C18 N8 Ca1 N4 121.8(2) . . . . ? C22 N8 Ca1 N4 -54.5(3) . . . . ? C18 N8 Ca1 Cl1 163.7(2) . . . . ? C22 N8 Ca1 Cl1 -12.6(3) . . . . ? C18 N8 Ca1 Cl2 68.0(2) . . . . ? C22 N8 Ca1 Cl2 -108.3(3) . . . . ? C11 N4 Ca1 N7 57.5(3) . . . . ? C7 N4 Ca1 N7 -134.2(2) . . . . ? C11 N4 Ca1 N3 179.2(3) . . . . ? C7 N4 Ca1 N3 -12.5(2) . . . . ? C11 N4 Ca1 N5 90.5(3) . . . . ? C7 N4 Ca1 N5 -101.2(2) . . . . ? C11 N4 Ca1 N1 169.5(2) . . . . ? C7 N4 Ca1 N1 -22.2(3) . . . . ? C11 N4 Ca1 N8 -58.4(3) . . . . ? C7 N4 Ca1 N8 109.9(3) . . . . ? C11 N4 Ca1 Cl1 -100.7(3) . . . . ? C7 N4 Ca1 Cl1 67.6(2) . . . . ? C11 N4 Ca1 Cl2 -4.5(3) . . . . ? C7 N4 Ca1 Cl2 163.8(2) . . . . ? 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 N2 H2N Cl2 0.95(3) 2.27(3) 3.210(3) 174(3) 4_565 N6 H6N Cl1 0.90(3) 2.26(3) 3.154(3) 177(3) 4_566 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.784 _refine_diff_density_min -0.675 _refine_diff_density_rms 0.129 _database_code_depnum_ccdc_archive 'CCDC 971153' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_jmlgv120116 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H10 Ca F6 N4 O6 S2' _chemical_formula_sum 'C13 H10 Ca F6 N4 O6 S2' _chemical_formula_weight 536.45 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' Ca Ca 0.2262 0.3064 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 8.8738(9) _cell_length_b 10.2258(10) _cell_length_c 11.1100(11) _cell_angle_alpha 92.066(2) _cell_angle_beta 98.016(2) _cell_angle_gamma 100.127(2) _cell_volume 980.84(17) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5678 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 30.05 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.816 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 540 _exptl_absorpt_coefficient_mu 0.631 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8334 _exptl_absorpt_correction_T_max 0.9692 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator triumph _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15522 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 30.30 _reflns_number_total 5770 _reflns_number_gt 4438 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^ > 2\s(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^)+(0.0276P)^2^+3.6407P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5770 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0742 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1409 _refine_ls_wR_factor_gt 0.1336 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.116 _refine_ls_shift/su_max 0.000 _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 0.2618(4) 0.2948(4) 0.1639(3) 0.0272(7) Uani 1 1 d . . . H1 H 0.2185 0.3734 0.1606 0.033 Uiso 1 1 calc R . . C2 C 0.3117(5) 0.2498(4) 0.0608(4) 0.0363(9) Uani 1 1 d . . . H2 H 0.3013 0.2951 -0.0122 0.044 Uiso 1 1 calc R . . C3 C 0.3777(5) 0.1360(4) 0.0666(4) 0.0378(10) Uani 1 1 d . . . H3 H 0.4157 0.1036 -0.0024 0.045 Uiso 1 1 calc R . . C4 C 0.3878(5) 0.0711(4) 0.1722(4) 0.0321(8) Uani 1 1 d . . . H4 H 0.4318 -0.0071 0.1780 0.038 Uiso 1 1 calc R . . C5 C 0.3314(4) 0.1232(3) 0.2713(3) 0.0227(7) Uani 1 1 d . . . C6 C 0.2411(4) 0.0218(3) 0.5550(3) 0.0215(7) Uani 1 1 d . . . H6 H 0.2832 -0.0573 0.5620 0.026 Uiso 1 1 calc R . . C7 C 0.1544(4) 0.0637(3) 0.6456(3) 0.0226(7) Uani 1 1 d . . . C8 C 0.1269(5) -0.0130(4) 0.7438(3) 0.0306(8) Uani 1 1 d . . . H8 H 0.1676 -0.0925 0.7537 0.037 Uiso 1 1 calc R . . C9 C 0.0396(5) 0.0278(4) 0.8268(4) 0.0368(9) Uani 1 1 d . . . H9 H 0.0197 -0.0230 0.8947 0.044 Uiso 1 1 calc R . . C10 C -0.0177(5) 0.1429(4) 0.8096(4) 0.0340(9) Uani 1 1 d . . . H10 H -0.0794 0.1725 0.8646 0.041 Uiso 1 1 calc R . . C11 C 0.0157(4) 0.2152(4) 0.7107(4) 0.0290(8) Uani 1 1 d . . . H11 H -0.0241 0.2950 0.6998 0.035 Uiso 1 1 calc R . . C12 C 0.5706(5) 0.3383(4) 0.7833(4) 0.0290(8) Uani 1 1 d . . . C13 C -0.1595(5) 0.4070(4) 0.1668(3) 0.0295(8) Uani 1 1 d . . . N1 N 0.2708(3) 0.2338(3) 0.2688(3) 0.0215(6) Uani 1 1 d . . . N2 N 0.3363(4) 0.0560(3) 0.3778(3) 0.0259(6) Uani 1 1 d . . . N3 N 0.2594(3) 0.0950(3) 0.4646(3) 0.0211(6) Uani 1 1 d . . . N4 N 0.1013(3) 0.1785(3) 0.6295(3) 0.0226(6) Uani 1 1 d . . . Ca1 Ca 0.20521(7) 0.33023(6) 0.46713(6) 0.01562(14) Uani 1 1 d . . . F1 F 0.4668(3) 0.2293(3) 0.7938(3) 0.0490(7) Uani 1 1 d . . . F2 F 0.5157(3) 0.4409(3) 0.8206(3) 0.0457(7) Uani 1 1 d . . . F3 F 0.6993(3) 0.3309(3) 0.8567(2) 0.0505(7) Uani 1 1 d . . . F4 F -0.2759(4) 0.4571(3) 0.1103(2) 0.0536(8) Uani 1 1 d . . . F5 F -0.1569(3) 0.2920(3) 0.1077(2) 0.0444(7) Uani 1 1 d . . . F6 F -0.0291(3) 0.4893(3) 0.1546(3) 0.0490(7) Uani 1 1 d . . . O1 O 0.4587(3) 0.3591(3) 0.5608(2) 0.0277(6) Uani 1 1 d . . . O2 O 0.6572(3) 0.2251(2) 0.6034(3) 0.0306(6) Uani 1 1 d . . . O3 O -0.0407(3) 0.3287(3) 0.3683(2) 0.0258(5) Uani 1 1 d . . . O4 O -0.3193(3) 0.2925(3) 0.3218(3) 0.0336(6) Uani 1 1 d . . . O5 O 0.1715(3) 0.4834(2) 0.6234(2) 0.0287(6) Uani 1 1 d . . . O6 O 0.2767(3) 0.5346(2) 0.3710(2) 0.0222(5) Uani 1 1 d . . . S1 S 0.60632(9) 0.34731(7) 0.62589(7) 0.01739(16) Uani 1 1 d . . . S2 S -0.17756(9) 0.38307(8) 0.32601(7) 0.01852(17) Uani 1 1 d . . . H2N H 0.360(5) -0.023(4) 0.375(4) 0.029(11) Uiso 1 1 d . . . 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 0.034(2) 0.0213(16) 0.0264(18) 0.0003(13) 0.0051(15) 0.0048(14) C2 0.049(3) 0.034(2) 0.028(2) 0.0043(16) 0.0126(18) 0.0091(18) C3 0.051(3) 0.032(2) 0.035(2) -0.0049(17) 0.0190(19) 0.0092(18) C4 0.040(2) 0.0240(17) 0.036(2) -0.0030(15) 0.0156(17) 0.0106(16) C5 0.0228(16) 0.0197(15) 0.0262(17) -0.0027(13) 0.0064(13) 0.0043(12) C6 0.0292(18) 0.0116(13) 0.0243(16) 0.0021(12) 0.0028(13) 0.0059(12) C7 0.0277(17) 0.0148(14) 0.0237(17) -0.0003(12) 0.0003(13) 0.0024(12) C8 0.045(2) 0.0185(16) 0.0261(18) 0.0025(14) 0.0029(16) 0.0022(15) C9 0.048(3) 0.031(2) 0.028(2) 0.0044(16) 0.0094(18) -0.0059(18) C10 0.033(2) 0.033(2) 0.035(2) 0.0007(16) 0.0110(17) -0.0011(16) C11 0.0239(18) 0.0241(17) 0.039(2) 0.0023(15) 0.0080(16) 0.0024(14) C12 0.032(2) 0.0292(18) 0.0265(18) 0.0047(15) 0.0077(15) 0.0042(15) C13 0.038(2) 0.0333(19) 0.0214(17) 0.0006(14) 0.0043(15) 0.0187(16) N1 0.0235(14) 0.0160(13) 0.0249(15) -0.0022(11) 0.0057(11) 0.0022(10) N2 0.0368(17) 0.0173(13) 0.0275(16) 0.0017(11) 0.0095(13) 0.0114(12) N3 0.0228(14) 0.0150(12) 0.0261(15) -0.0008(11) 0.0041(11) 0.0049(10) N4 0.0223(14) 0.0183(13) 0.0273(15) 0.0051(11) 0.0028(12) 0.0036(11) Ca1 0.0176(3) 0.0122(3) 0.0178(3) 0.0010(2) 0.0019(2) 0.0053(2) F1 0.0610(18) 0.0382(14) 0.0451(16) 0.0139(12) 0.0209(14) -0.0107(12) F2 0.0554(17) 0.0432(15) 0.0452(16) -0.0045(12) 0.0257(13) 0.0141(12) F3 0.0494(16) 0.078(2) 0.0232(12) 0.0082(13) -0.0061(11) 0.0169(15) F4 0.0684(19) 0.076(2) 0.0285(13) 0.0132(13) -0.0013(13) 0.0498(17) F5 0.0740(19) 0.0396(14) 0.0245(12) -0.0068(10) 0.0074(12) 0.0256(13) F6 0.0614(18) 0.0490(16) 0.0420(15) 0.0082(12) 0.0277(14) 0.0076(13) O1 0.0193(12) 0.0284(13) 0.0334(14) 0.0053(11) -0.0051(10) 0.0056(10) O2 0.0392(16) 0.0179(12) 0.0378(15) 0.0015(11) 0.0050(12) 0.0141(11) O3 0.0227(12) 0.0285(13) 0.0258(13) -0.0013(10) -0.0038(10) 0.0102(10) O4 0.0219(13) 0.0362(15) 0.0391(16) -0.0012(12) 0.0004(11) -0.0008(11) O5 0.0422(16) 0.0207(12) 0.0263(13) -0.0035(10) 0.0106(11) 0.0110(11) O6 0.0231(12) 0.0175(11) 0.0256(13) 0.0062(9) 0.0039(10) 0.0013(9) S1 0.0182(4) 0.0132(3) 0.0211(4) 0.0030(3) 0.0007(3) 0.0053(3) S2 0.0196(4) 0.0179(4) 0.0187(4) -0.0011(3) 0.0015(3) 0.0065(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.340(5) . ? C1 C2 1.377(5) . ? C1 H1 0.9500 . ? C2 C3 1.391(6) . ? C2 H2 0.9500 . ? C3 C4 1.369(6) . ? C3 H3 0.9500 . ? C4 C5 1.396(5) . ? C4 H4 0.9500 . ? C5 N1 1.335(4) . ? C5 N2 1.389(5) . ? C6 N3 1.285(4) . ? C6 C7 1.446(5) . ? C6 H6 0.9500 . ? C7 N4 1.348(4) . ? C7 C8 1.391(5) . ? C8 C9 1.382(6) . ? C8 H8 0.9500 . ? C9 C10 1.371(6) . ? C9 H9 0.9500 . ? C10 C11 1.383(6) . ? C10 H10 0.9500 . ? C11 N4 1.341(5) . ? C11 H11 0.9500 . ? C12 F2 1.310(4) . ? C12 F3 1.323(5) . ? C12 F1 1.335(4) . ? C12 S1 1.823(4) . ? C13 F4 1.323(4) . ? C13 F5 1.331(4) . ? C13 F6 1.333(5) . ? C13 S2 1.820(4) . ? N1 Ca1 2.563(3) . ? N2 N3 1.344(4) . ? N2 H2N 0.87(4) . ? N3 Ca1 2.534(3) . ? N4 Ca1 2.583(3) . ? Ca1 O3 2.299(3) . ? Ca1 O1 2.306(3) . ? Ca1 O5 2.381(2) . ? Ca1 O6 2.408(2) . ? O1 S1 1.433(3) . ? O2 S1 1.427(2) . ? O3 S2 1.449(2) . ? O4 S2 1.419(3) . ? O5 S2 1.447(2) 2_566 ? O6 S1 1.443(2) 2_666 ? S1 O6 1.443(2) 2_666 ? S2 O5 1.447(2) 2_566 ? 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 123.7(3) . . ? N1 C1 H1 118.2 . . ? C2 C1 H1 118.2 . . ? C1 C2 C3 118.1(4) . . ? C1 C2 H2 121.0 . . ? C3 C2 H2 121.0 . . ? C4 C3 C2 119.6(4) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 118.1(3) . . ? C3 C4 H4 121.0 . . ? C5 C4 H4 121.0 . . ? N1 C5 N2 117.9(3) . . ? N1 C5 C4 123.4(3) . . ? N2 C5 C4 118.7(3) . . ? N3 C6 C7 117.8(3) . . ? N3 C6 H6 121.1 . . ? C7 C6 H6 121.1 . . ? N4 C7 C8 122.3(3) . . ? N4 C7 C6 117.1(3) . . ? C8 C7 C6 120.7(3) . . ? C9 C8 C7 119.2(4) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C10 C9 C8 118.9(4) . . ? C10 C9 H9 120.6 . . ? C8 C9 H9 120.6 . . ? C9 C10 C11 118.9(4) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? N4 C11 C10 123.5(4) . . ? N4 C11 H11 118.3 . . ? C10 C11 H11 118.3 . . ? F2 C12 F3 108.7(3) . . ? F2 C12 F1 107.5(3) . . ? F3 C12 F1 107.9(3) . . ? F2 C12 S1 112.3(3) . . ? F3 C12 S1 110.6(3) . . ? F1 C12 S1 109.8(3) . . ? F4 C13 F5 107.8(3) . . ? F4 C13 F6 107.4(3) . . ? F5 C13 F6 107.0(3) . . ? F4 C13 S2 111.9(3) . . ? F5 C13 S2 110.8(3) . . ? F6 C13 S2 111.8(3) . . ? C5 N1 C1 117.1(3) . . ? C5 N1 Ca1 118.8(2) . . ? C1 N1 Ca1 123.7(2) . . ? N3 N2 C5 117.6(3) . . ? N3 N2 H2N 121(3) . . ? C5 N2 H2N 118(3) . . ? C6 N3 N2 118.7(3) . . ? C6 N3 Ca1 121.6(2) . . ? N2 N3 Ca1 118.4(2) . . ? C11 N4 C7 117.3(3) . . ? C11 N4 Ca1 123.9(2) . . ? C7 N4 Ca1 118.1(2) . . ? O3 Ca1 O1 172.88(10) . . ? O3 Ca1 O5 91.39(9) . . ? O1 Ca1 O5 85.67(10) . . ? O3 Ca1 O6 85.69(9) . . ? O1 Ca1 O6 87.44(9) . . ? O5 Ca1 O6 81.01(9) . . ? O3 Ca1 N3 109.38(9) . . ? O1 Ca1 N3 77.17(9) . . ? O5 Ca1 N3 133.90(10) . . ? O6 Ca1 N3 139.17(9) . . ? O3 Ca1 N1 88.37(9) . . ? O1 Ca1 N1 92.41(10) . . ? O5 Ca1 N1 161.94(9) . . ? O6 Ca1 N1 80.97(9) . . ? N3 Ca1 N1 62.49(9) . . ? O3 Ca1 N4 91.88(10) . . ? O1 Ca1 N4 93.73(10) . . ? O5 Ca1 N4 76.44(9) . . ? O6 Ca1 N4 157.25(9) . . ? N3 Ca1 N4 62.64(9) . . ? N1 Ca1 N4 121.62(9) . . ? S1 O1 Ca1 167.31(17) . . ? S2 O3 Ca1 156.65(16) . . ? S2 O5 Ca1 152.24(17) 2_566 . ? S1 O6 Ca1 144.35(15) 2_666 . ? O2 S1 O1 115.84(17) . . ? O2 S1 O6 114.98(16) . 2_666 ? O1 S1 O6 114.02(15) . 2_666 ? O2 S1 C12 102.68(17) . . ? O1 S1 C12 103.22(17) . . ? O6 S1 C12 103.70(17) 2_666 . ? O4 S2 O5 116.87(17) . 2_566 ? O4 S2 O3 114.56(17) . . ? O5 S2 O3 113.21(16) 2_566 . ? O4 S2 C13 104.19(19) . . ? O5 S2 C13 103.39(17) 2_566 . ? O3 S2 C13 102.24(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -1.2(7) . . . . ? C1 C2 C3 C4 1.5(7) . . . . ? C2 C3 C4 C5 -0.5(7) . . . . ? C3 C4 C5 N1 -1.1(6) . . . . ? C3 C4 C5 N2 178.0(4) . . . . ? N3 C6 C7 N4 -1.2(5) . . . . ? N3 C6 C7 C8 178.2(3) . . . . ? N4 C7 C8 C9 1.3(6) . . . . ? C6 C7 C8 C9 -178.1(4) . . . . ? C7 C8 C9 C10 0.2(6) . . . . ? C8 C9 C10 C11 -1.0(6) . . . . ? C9 C10 C11 N4 0.4(6) . . . . ? N2 C5 N1 C1 -177.6(3) . . . . ? C4 C5 N1 C1 1.5(5) . . . . ? N2 C5 N1 Ca1 8.6(4) . . . . ? C4 C5 N1 Ca1 -172.3(3) . . . . ? C2 C1 N1 C5 -0.3(6) . . . . ? C2 C1 N1 Ca1 173.2(3) . . . . ? N1 C5 N2 N3 9.7(5) . . . . ? C4 C5 N2 N3 -169.4(3) . . . . ? C7 C6 N3 N2 -178.3(3) . . . . ? C7 C6 N3 Ca1 14.5(4) . . . . ? C5 N2 N3 C6 169.0(3) . . . . ? C5 N2 N3 Ca1 -23.5(4) . . . . ? C10 C11 N4 C7 1.1(6) . . . . ? C10 C11 N4 Ca1 -168.8(3) . . . . ? C8 C7 N4 C11 -1.9(5) . . . . ? C6 C7 N4 C11 177.5(3) . . . . ? C8 C7 N4 Ca1 168.6(3) . . . . ? C6 C7 N4 Ca1 -12.0(4) . . . . ? C6 N3 Ca1 O3 -96.3(3) . . . . ? N2 N3 Ca1 O3 96.5(3) . . . . ? C6 N3 Ca1 O1 86.6(3) . . . . ? N2 N3 Ca1 O1 -80.6(3) . . . . ? C6 N3 Ca1 O5 15.7(3) . . . . ? N2 N3 Ca1 O5 -151.5(2) . . . . ? C6 N3 Ca1 O6 157.1(2) . . . . ? N2 N3 Ca1 O6 -10.0(3) . . . . ? C6 N3 Ca1 N1 -173.7(3) . . . . ? N2 N3 Ca1 N1 19.1(2) . . . . ? C6 N3 Ca1 N4 -14.5(3) . . . . ? N2 N3 Ca1 N4 178.3(3) . . . . ? C5 N1 Ca1 O3 -127.0(3) . . . . ? C1 N1 Ca1 O3 59.7(3) . . . . ? C5 N1 Ca1 O1 60.1(3) . . . . ? C1 N1 Ca1 O1 -113.2(3) . . . . ? C5 N1 Ca1 O5 143.5(3) . . . . ? C1 N1 Ca1 O5 -29.8(5) . . . . ? C5 N1 Ca1 O6 147.2(3) . . . . ? C1 N1 Ca1 O6 -26.2(3) . . . . ? C5 N1 Ca1 N3 -14.1(2) . . . . ? C1 N1 Ca1 N3 172.6(3) . . . . ? C5 N1 Ca1 N4 -35.7(3) . . . . ? C1 N1 Ca1 N4 150.9(3) . . . . ? C11 N4 Ca1 O3 -66.2(3) . . . . ? C7 N4 Ca1 O3 124.0(3) . . . . ? C11 N4 Ca1 O1 109.4(3) . . . . ? C7 N4 Ca1 O1 -60.4(3) . . . . ? C11 N4 Ca1 O5 24.8(3) . . . . ? C7 N4 Ca1 O5 -145.0(3) . . . . ? C11 N4 Ca1 O6 17.1(4) . . . . ? C7 N4 Ca1 O6 -152.7(2) . . . . ? C11 N4 Ca1 N3 -177.1(3) . . . . ? C7 N4 Ca1 N3 13.1(2) . . . . ? C11 N4 Ca1 N1 -155.5(3) . . . . ? C7 N4 Ca1 N1 34.7(3) . . . . ? O5 Ca1 O1 S1 110.7(8) . . . . ? O6 Ca1 O1 S1 -168.1(8) . . . . ? N3 Ca1 O1 S1 -26.2(8) . . . . ? N1 Ca1 O1 S1 -87.3(8) . . . . ? N4 Ca1 O1 S1 34.6(8) . . . . ? O5 Ca1 O3 S2 34.6(4) . . . . ? O6 Ca1 O3 S2 -46.2(4) . . . . ? N3 Ca1 O3 S2 172.7(4) . . . . ? N1 Ca1 O3 S2 -127.3(4) . . . . ? N4 Ca1 O3 S2 111.1(4) . . . . ? O3 Ca1 O5 S2 -87.3(4) . . . 2_566 ? O1 Ca1 O5 S2 86.2(4) . . . 2_566 ? O6 Ca1 O5 S2 -1.9(4) . . . 2_566 ? N3 Ca1 O5 S2 153.8(3) . . . 2_566 ? N1 Ca1 O5 S2 1.7(6) . . . 2_566 ? N4 Ca1 O5 S2 -178.9(4) . . . 2_566 ? O3 Ca1 O6 S1 162.8(3) . . . 2_666 ? O1 Ca1 O6 S1 -15.4(3) . . . 2_666 ? O5 Ca1 O6 S1 70.7(3) . . . 2_666 ? N3 Ca1 O6 S1 -82.3(3) . . . 2_666 ? N1 Ca1 O6 S1 -108.2(3) . . . 2_666 ? N4 Ca1 O6 S1 78.2(4) . . . 2_666 ? Ca1 O1 S1 O2 42.5(9) . . . . ? Ca1 O1 S1 O6 179.3(8) . . . 2_666 ? Ca1 O1 S1 C12 -68.9(8) . . . . ? F2 C12 S1 O2 -177.3(3) . . . . ? F3 C12 S1 O2 61.1(3) . . . . ? F1 C12 S1 O2 -57.8(3) . . . . ? F2 C12 S1 O1 -56.5(3) . . . . ? F3 C12 S1 O1 -178.1(3) . . . . ? F1 C12 S1 O1 62.9(3) . . . . ? F2 C12 S1 O6 62.7(3) . . . 2_666 ? F3 C12 S1 O6 -58.9(3) . . . 2_666 ? F1 C12 S1 O6 -177.9(3) . . . 2_666 ? Ca1 O3 S2 O4 -145.0(4) . . . . ? Ca1 O3 S2 O5 -7.5(5) . . . 2_566 ? Ca1 O3 S2 C13 103.0(4) . . . . ? F4 C13 S2 O4 60.5(3) . . . . ? F5 C13 S2 O4 -59.8(3) . . . . ? F6 C13 S2 O4 -179.1(3) . . . . ? F4 C13 S2 O5 -62.2(3) . . . 2_566 ? F5 C13 S2 O5 177.5(3) . . . 2_566 ? F6 C13 S2 O5 58.3(3) . . . 2_566 ? F4 C13 S2 O3 -180.0(3) . . . . ? F5 C13 S2 O3 59.7(3) . . . . ? F6 C13 S2 O3 -59.5(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 N2 H2N O2 0.87(4) 2.07(4) 2.900(4) 159(4) 2_656 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 30.30 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.632 _refine_diff_density_min -0.502 _refine_diff_density_rms 0.100 _database_code_depnum_ccdc_archive 'CCDC 971154' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_jmlnh130523 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H29 Ca N12, 2(Cl O4)' _chemical_formula_sum 'C33 H29 Ca Cl2 N12 O8' _chemical_formula_weight 832.66 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 11.208(2) _cell_length_b 19.890(4) _cell_length_c 18.423(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.346(4) _cell_angle_gamma 90.00 _cell_volume 4081.9(14) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5926 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 28.69 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1716 _exptl_absorpt_coefficient_mu 0.347 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8737 _exptl_absorpt_correction_T_max 0.9183 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20273 _diffrn_reflns_av_R_equivalents 0.0598 _diffrn_reflns_av_sigmaI/netI 0.0610 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 28.99 _reflns_number_total 5241 _reflns_number_gt 3589 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^ > 2\s(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^)+(0.0625P)^2^+22.8172P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5241 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1083 _refine_ls_R_factor_gt 0.0790 _refine_ls_wR_factor_ref 0.2130 _refine_ls_wR_factor_gt 0.2021 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _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 0.1639(4) -0.0804(2) 0.4009(3) 0.0495(11) Uani 1 1 d . . . H1 H 0.0866 -0.0989 0.4042 0.059 Uiso 1 1 calc R . . C2 C 0.2593(5) -0.1047(3) 0.4484(3) 0.0570(13) Uani 1 1 d . . . H2 H 0.2473 -0.1387 0.4831 0.068 Uiso 1 1 calc R . . C3 C 0.3723(4) -0.0779(3) 0.4435(3) 0.0565(13) Uani 1 1 d . . . H3 H 0.4395 -0.0931 0.4753 0.068 Uiso 1 1 calc R . . C4 C 0.3859(4) -0.0293(2) 0.3924(3) 0.0506(11) Uani 1 1 d . . . H4 H 0.4625 -0.0102 0.3880 0.061 Uiso 1 1 calc R . . C5 C 0.2847(4) -0.0083(2) 0.3469(2) 0.0382(9) Uani 1 1 d . . . C6 C 0.2986(3) 0.04284(19) 0.2948(2) 0.0335(8) Uani 1 1 d . . . H6 H 0.3760 0.0604 0.2895 0.040 Uiso 1 1 calc R . . C7 C 0.1211(3) 0.14090(18) 0.1616(2) 0.0310(8) Uani 1 1 d . . . C8 C 0.1382(4) 0.1966(2) 0.1169(3) 0.0475(11) Uani 1 1 d . . . H8 H 0.2143 0.2180 0.1190 0.057 Uiso 1 1 calc R . . C9 C 0.0428(5) 0.2197(2) 0.0701(3) 0.0560(13) Uani 1 1 d . . . H9 H 0.0521 0.2572 0.0393 0.067 Uiso 1 1 calc R . . C10 C -0.0674(4) 0.1872(2) 0.0687(3) 0.0507(11) Uani 1 1 d . . . H10 H -0.1351 0.2023 0.0373 0.061 Uiso 1 1 calc R . . C11 C -0.0760(4) 0.1327(2) 0.1138(2) 0.0439(10) Uani 1 1 d . . . H11 H -0.1514 0.1106 0.1122 0.053 Uiso 1 1 calc R . . C12 C 0.1946(4) -0.0265(2) 0.1082(2) 0.0452(10) Uani 1 1 d . . . H12 H 0.1837 0.0203 0.0996 0.054 Uiso 1 1 calc R . . C13 C 0.2743(4) -0.0608(2) 0.0691(2) 0.0485(11) Uani 1 1 d . . . H13 H 0.3166 -0.0378 0.0347 0.058 Uiso 1 1 calc R . . C14 C 0.2911(4) -0.1288(2) 0.0810(3) 0.0509(12) Uani 1 1 d . . . H14 H 0.3459 -0.1533 0.0553 0.061 Uiso 1 1 calc R . . C15 C 0.2276(4) -0.1604(2) 0.1303(3) 0.0447(10) Uani 1 1 d . A . H15 H 0.2374 -0.2072 0.1394 0.054 Uiso 1 1 calc R . . C16 C 0.1479(3) -0.12274(18) 0.1673(2) 0.0339(8) Uani 1 1 d . . . C17 C 0.0772(4) -0.15623(18) 0.2146(2) 0.0432(9) Uani 0.50 1 d P A 1 H17 H 0.0845 -0.2035 0.2214 0.052 Uiso 0.50 1 calc PR A 1 N1 N 0.1743(3) -0.03272(17) 0.3509(2) 0.0397(8) Uani 1 1 d . . . N2 N 0.2029(3) 0.06604(14) 0.25347(18) 0.0315(7) Uani 1 1 d . . . N3 N 0.2188(3) 0.11652(18) 0.2086(2) 0.0430(8) Uani 1 1 d . . . H3N H 0.2904 0.1347 0.2082 0.052 Uiso 1 1 calc R . . N4 N 0.0151(3) 0.10865(15) 0.15973(18) 0.0339(7) Uani 1 1 d . . . N5 N 0.1317(3) -0.05618(16) 0.15777(19) 0.0360(7) Uani 1 1 d . A . N6 N 0.0772(4) -0.15623(18) 0.2146(2) 0.0432(9) Uani 0.50 1 d P A 2 N7 N 0.0000 -0.1213(2) 0.2500 0.0337(10) Uani 1 2 d S . . O1 O 0.6031(4) 0.19247(19) 0.1851(2) 0.0715(11) Uani 1 1 d . . . O2 O 0.5832(4) 0.1674(3) 0.0621(2) 0.0828(13) Uani 1 1 d . . . O3 O 0.4560(4) 0.1168(2) 0.1380(3) 0.0833(13) Uani 1 1 d . . . O4 O 0.4372(3) 0.2326(2) 0.1091(3) 0.0811(13) Uani 1 1 d . . . Cl1 Cl 0.51849(9) 0.17728(6) 0.12285(6) 0.0456(3) Uani 1 1 d . . . Ca1 Ca 0.0000 0.00667(5) 0.2500 0.0289(2) Uani 1 2 d S . . 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 0.050(2) 0.044(2) 0.053(3) 0.012(2) 0.004(2) 0.002(2) C2 0.067(3) 0.049(3) 0.054(3) 0.017(2) 0.002(2) 0.010(2) C3 0.048(3) 0.063(3) 0.056(3) 0.015(2) -0.004(2) 0.025(2) C4 0.041(2) 0.051(3) 0.058(3) 0.004(2) -0.002(2) 0.013(2) C5 0.038(2) 0.0347(19) 0.041(2) 0.0011(16) 0.0032(17) 0.0107(16) C6 0.0225(16) 0.0345(18) 0.043(2) 0.0068(16) -0.0004(15) 0.0029(13) C7 0.0317(17) 0.0269(16) 0.034(2) 0.0012(14) 0.0033(15) -0.0026(13) C8 0.048(2) 0.043(2) 0.052(3) 0.014(2) 0.006(2) -0.0114(19) C9 0.066(3) 0.047(3) 0.054(3) 0.020(2) -0.001(2) -0.009(2) C10 0.053(3) 0.045(2) 0.050(3) 0.011(2) -0.011(2) 0.000(2) C11 0.040(2) 0.042(2) 0.046(3) 0.0067(19) -0.0069(19) -0.0057(17) C12 0.055(3) 0.038(2) 0.046(3) 0.0023(18) 0.021(2) -0.0051(19) C13 0.049(2) 0.056(3) 0.044(3) -0.006(2) 0.023(2) -0.009(2) C14 0.045(2) 0.055(3) 0.058(3) -0.017(2) 0.027(2) -0.001(2) C15 0.043(2) 0.036(2) 0.057(3) -0.0092(19) 0.018(2) 0.0034(17) C16 0.0327(18) 0.0297(17) 0.041(2) -0.0065(15) 0.0109(16) -0.0009(14) C17 0.057(2) 0.0261(17) 0.049(2) -0.0001(15) 0.0184(19) 0.0072(16) N1 0.0384(17) 0.0342(16) 0.047(2) 0.0095(15) 0.0055(15) 0.0055(14) N2 0.0273(14) 0.0255(14) 0.0421(19) 0.0039(12) 0.0056(13) 0.0034(11) N3 0.0283(16) 0.0442(19) 0.057(2) 0.0089(17) 0.0062(15) -0.0035(14) N4 0.0320(15) 0.0300(15) 0.0394(19) 0.0053(13) 0.0026(14) -0.0041(12) N5 0.0381(17) 0.0298(15) 0.0432(19) -0.0001(13) 0.0174(14) 0.0009(13) N6 0.057(2) 0.0261(17) 0.049(2) -0.0001(15) 0.0184(19) 0.0072(16) N7 0.041(2) 0.027(2) 0.036(3) 0.000 0.014(2) 0.000 O1 0.090(3) 0.056(2) 0.061(2) 0.0002(18) -0.023(2) -0.006(2) O2 0.079(3) 0.113(4) 0.063(3) -0.013(2) 0.037(2) -0.007(3) O3 0.069(3) 0.065(2) 0.123(4) -0.016(2) 0.043(2) -0.024(2) O4 0.054(2) 0.081(3) 0.107(4) 0.006(2) 0.000(2) 0.017(2) Cl1 0.0404(5) 0.0539(6) 0.0438(6) -0.0044(5) 0.0103(4) -0.0024(4) Ca1 0.0288(5) 0.0232(5) 0.0358(6) 0.000 0.0081(4) 0.000 _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.337(5) . ? C1 C2 1.391(7) . ? C1 H1 0.9500 . ? C2 C3 1.387(7) . ? C2 H2 0.9500 . ? C3 C4 1.371(7) . ? C3 H3 0.9500 . ? C4 C5 1.399(6) . ? C4 H4 0.9500 . ? C5 N1 1.338(5) . ? C5 C6 1.419(5) . ? C6 N2 1.328(5) . ? C6 H6 0.9500 . ? C7 N4 1.347(4) . ? C7 C8 1.406(5) . ? C7 N3 1.406(5) . ? C8 C9 1.376(7) . ? C8 H8 0.9500 . ? C9 C10 1.392(7) . ? C9 H9 0.9500 . ? C10 C11 1.376(6) . ? C10 H10 0.9500 . ? C11 N4 1.341(5) . ? C11 H11 0.9500 . ? C12 N5 1.350(5) . ? C12 C13 1.387(6) . ? C12 H12 0.9500 . ? C13 C14 1.379(7) . ? C13 H13 0.9500 . ? C14 C15 1.368(6) . ? C14 H14 0.9500 . ? C15 C16 1.398(5) . ? C15 H15 0.9500 . ? C16 N5 1.345(5) . ? C16 C17 1.409(5) . ? C17 N7 1.335(4) . ? C17 H17 0.9500 . ? N1 Ca1 2.662(3) . ? N2 N3 1.325(4) . ? N2 Ca1 2.557(3) . ? N3 H3N 0.8800 . ? N4 Ca1 2.640(3) . ? N5 Ca1 2.680(3) . ? N7 N6 1.335(4) 2 ? N7 C17 1.335(4) 2 ? N7 Ca1 2.545(4) . ? O1 Cl1 1.437(4) . ? O2 Cl1 1.413(4) . ? O3 Cl1 1.434(4) . ? O4 Cl1 1.433(4) . ? Ca1 N2 2.557(3) 2 ? Ca1 N4 2.640(3) 2 ? Ca1 N1 2.662(3) 2 ? Ca1 N5 2.680(3) 2 ? 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 124.1(5) . . ? N1 C1 H1 117.9 . . ? C2 C1 H1 117.9 . . ? C3 C2 C1 118.0(4) . . ? C3 C2 H2 121.0 . . ? C1 C2 H2 121.0 . . ? C4 C3 C2 119.2(4) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 118.6(5) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? N1 C5 C4 123.5(4) . . ? N1 C5 C6 118.0(3) . . ? C4 C5 C6 118.5(4) . . ? N2 C6 C5 119.6(3) . . ? N2 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? N4 C7 C8 122.5(4) . . ? N4 C7 N3 118.4(3) . . ? C8 C7 N3 119.0(3) . . ? C9 C8 C7 118.9(4) . . ? C9 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? C8 C9 C10 118.9(4) . . ? C8 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? C11 C10 C9 118.4(4) . . ? C11 C10 H10 120.8 . . ? C9 C10 H10 120.8 . . ? N4 C11 C10 124.3(4) . . ? N4 C11 H11 117.9 . . ? C10 C11 H11 117.9 . . ? N5 C12 C13 123.4(4) . . ? N5 C12 H12 118.3 . . ? C13 C12 H12 118.3 . . ? C14 C13 C12 119.0(4) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C15 C14 C13 118.9(4) . . ? C15 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? C14 C15 C16 119.0(4) . . ? C14 C15 H15 120.5 . . ? C16 C15 H15 120.5 . . ? N5 C16 C15 123.2(4) . . ? N5 C16 C17 117.9(3) . . ? C15 C16 C17 118.8(3) . . ? N7 C17 C16 119.7(3) . . ? N7 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C1 N1 C5 116.6(4) . . ? C1 N1 Ca1 125.3(3) . . ? C5 N1 Ca1 117.8(3) . . ? N3 N2 C6 117.7(3) . . ? N3 N2 Ca1 121.0(2) . . ? C6 N2 Ca1 120.9(2) . . ? N2 N3 C7 119.7(3) . . ? N2 N3 H3N 120.1 . . ? C7 N3 H3N 120.1 . . ? C11 N4 C7 117.0(3) . . ? C11 N4 Ca1 125.1(3) . . ? C7 N4 Ca1 117.9(2) . . ? C16 N5 C12 116.5(3) . . ? C16 N5 Ca1 116.9(2) . . ? C12 N5 Ca1 126.2(3) . . ? N6 N7 C17 117.2(4) 2 . ? C17 N7 C17 117.2(4) 2 . ? N6 N7 Ca1 121.4(2) 2 . ? C17 N7 Ca1 121.4(2) 2 . ? C17 N7 Ca1 121.4(2) . . ? O2 Cl1 O4 109.8(3) . . ? O2 Cl1 O3 110.0(3) . . ? O4 Cl1 O3 111.3(3) . . ? O2 Cl1 O1 108.0(3) . . ? O4 Cl1 O1 109.3(3) . . ? O3 Cl1 O1 108.4(3) . . ? N7 Ca1 N2 117.51(7) . . ? N7 Ca1 N2 117.51(7) . 2 ? N2 Ca1 N2 124.98(13) . 2 ? N7 Ca1 N4 140.20(7) . 2 ? N2 Ca1 N4 75.42(10) . 2 ? N2 Ca1 N4 62.75(10) 2 2 ? N7 Ca1 N4 140.20(7) . . ? N2 Ca1 N4 62.75(10) . . ? N2 Ca1 N4 75.42(10) 2 . ? N4 Ca1 N4 79.61(15) 2 . ? N7 Ca1 N1 72.88(8) . . ? N2 Ca1 N1 62.38(10) . . ? N2 Ca1 N1 137.36(11) 2 . ? N4 Ca1 N1 83.08(10) 2 . ? N4 Ca1 N1 124.95(10) . . ? N7 Ca1 N1 72.88(8) . 2 ? N2 Ca1 N1 137.36(11) . 2 ? N2 Ca1 N1 62.38(10) 2 2 ? N4 Ca1 N1 124.95(10) 2 2 ? N4 Ca1 N1 83.08(10) . 2 ? N1 Ca1 N1 145.76(15) . 2 ? N7 Ca1 N5 62.19(7) . 2 ? N2 Ca1 N5 138.61(11) . 2 ? N2 Ca1 N5 71.38(10) 2 2 ? N4 Ca1 N5 83.16(10) 2 2 ? N4 Ca1 N5 146.71(10) . 2 ? N1 Ca1 N5 80.39(11) . 2 ? N1 Ca1 N5 83.82(11) 2 2 ? N7 Ca1 N5 62.19(7) . . ? N2 Ca1 N5 71.38(10) . . ? N2 Ca1 N5 138.61(11) 2 . ? N4 Ca1 N5 146.71(10) 2 . ? N4 Ca1 N5 83.16(10) . . ? N1 Ca1 N5 83.82(11) . . ? N1 Ca1 N5 80.39(11) 2 . ? N5 Ca1 N5 124.39(14) 2 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -0.2(8) . . . . ? C1 C2 C3 C4 -0.3(8) . . . . ? C2 C3 C4 C5 0.0(8) . . . . ? C3 C4 C5 N1 0.8(7) . . . . ? C3 C4 C5 C6 179.0(4) . . . . ? N1 C5 C6 N2 1.8(6) . . . . ? C4 C5 C6 N2 -176.5(4) . . . . ? N4 C7 C8 C9 0.8(7) . . . . ? N3 C7 C8 C9 179.0(4) . . . . ? C7 C8 C9 C10 0.1(8) . . . . ? C8 C9 C10 C11 -0.7(8) . . . . ? C9 C10 C11 N4 0.4(8) . . . . ? N5 C12 C13 C14 0.0(8) . . . . ? C12 C13 C14 C15 0.7(7) . . . . ? C13 C14 C15 C16 -0.2(7) . . . . ? C14 C15 C16 N5 -1.2(7) . . . . ? C14 C15 C16 C17 176.1(4) . . . . ? N5 C16 C17 N7 -2.0(6) . . . . ? C15 C16 C17 N7 -179.5(4) . . . . ? C2 C1 N1 C5 0.9(7) . . . . ? C2 C1 N1 Ca1 173.4(4) . . . . ? C4 C5 N1 C1 -1.2(6) . . . . ? C6 C5 N1 C1 -179.5(4) . . . . ? C4 C5 N1 Ca1 -174.3(3) . . . . ? C6 C5 N1 Ca1 7.4(5) . . . . ? C5 C6 N2 N3 176.1(4) . . . . ? C5 C6 N2 Ca1 -10.8(5) . . . . ? C6 N2 N3 C7 177.3(4) . . . . ? Ca1 N2 N3 C7 4.2(5) . . . . ? N4 C7 N3 N2 -4.9(6) . . . . ? C8 C7 N3 N2 176.9(4) . . . . ? C10 C11 N4 C7 0.5(7) . . . . ? C10 C11 N4 Ca1 177.9(4) . . . . ? C8 C7 N4 C11 -1.1(6) . . . . ? N3 C7 N4 C11 -179.3(4) . . . . ? C8 C7 N4 Ca1 -178.7(3) . . . . ? N3 C7 N4 Ca1 3.1(4) . . . . ? C15 C16 N5 C12 1.9(6) . . . . ? C17 C16 N5 C12 -175.5(4) . . . . ? C15 C16 N5 Ca1 -170.8(3) . . . . ? C17 C16 N5 Ca1 11.8(5) . . . . ? C13 C12 N5 C16 -1.2(7) . . . . ? C13 C12 N5 Ca1 170.7(3) . . . . ? C16 C17 N7 N6 170.2(5) . . . 2 ? C16 C17 N7 C17 170.2(5) . . . 2 ? C16 C17 N7 Ca1 -9.8(5) . . . . ? N6 N7 Ca1 N2 143.8(2) 2 . . . ? C17 N7 Ca1 N2 143.8(2) 2 . . . ? C17 N7 Ca1 N2 -36.2(2) . . . . ? N6 N7 Ca1 N2 -36.2(2) 2 . . 2 ? C17 N7 Ca1 N2 -36.2(2) 2 . . 2 ? C17 N7 Ca1 N2 143.8(2) . . . 2 ? N6 N7 Ca1 N4 43.3(2) 2 . . 2 ? C17 N7 Ca1 N4 43.3(2) 2 . . 2 ? C17 N7 Ca1 N4 -136.7(2) . . . 2 ? N6 N7 Ca1 N4 -136.7(2) 2 . . . ? C17 N7 Ca1 N4 -136.7(2) 2 . . . ? C17 N7 Ca1 N4 43.3(2) . . . . ? N6 N7 Ca1 N1 98.8(2) 2 . . . ? C17 N7 Ca1 N1 98.8(2) 2 . . . ? C17 N7 Ca1 N1 -81.2(2) . . . . ? N6 N7 Ca1 N1 -81.2(2) 2 . . 2 ? C17 N7 Ca1 N1 -81.2(2) 2 . . 2 ? C17 N7 Ca1 N1 98.8(2) . . . 2 ? N6 N7 Ca1 N5 10.8(2) 2 . . 2 ? C17 N7 Ca1 N5 10.8(2) 2 . . 2 ? C17 N7 Ca1 N5 -169.2(2) . . . 2 ? N6 N7 Ca1 N5 -169.2(2) 2 . . . ? C17 N7 Ca1 N5 -169.2(2) 2 . . . ? C17 N7 Ca1 N5 10.8(2) . . . . ? N3 N2 Ca1 N7 133.1(3) . . . . ? C6 N2 Ca1 N7 -39.8(3) . . . . ? N3 N2 Ca1 N2 -46.9(3) . . . 2 ? C6 N2 Ca1 N2 140.2(3) . . . 2 ? N3 N2 Ca1 N4 -87.4(3) . . . 2 ? C6 N2 Ca1 N4 99.7(3) . . . 2 ? N3 N2 Ca1 N4 -1.8(3) . . . . ? C6 N2 Ca1 N4 -174.7(3) . . . . ? N3 N2 Ca1 N1 -177.2(3) . . . . ? C6 N2 Ca1 N1 9.9(3) . . . . ? N3 N2 Ca1 N1 38.8(3) . . . 2 ? C6 N2 Ca1 N1 -134.1(3) . . . 2 ? N3 N2 Ca1 N5 -148.7(3) . . . 2 ? C6 N2 Ca1 N5 38.4(4) . . . 2 ? N3 N2 Ca1 N5 90.1(3) . . . . ? C6 N2 Ca1 N5 -82.8(3) . . . . ? C11 N4 Ca1 N7 80.7(4) . . . . ? C7 N4 Ca1 N7 -101.9(3) . . . . ? C11 N4 Ca1 N2 -178.1(4) . . . . ? C7 N4 Ca1 N2 -0.8(3) . . . . ? C11 N4 Ca1 N2 -35.0(3) . . . 2 ? C7 N4 Ca1 N2 142.4(3) . . . 2 ? C11 N4 Ca1 N4 -99.3(4) . . . 2 ? C7 N4 Ca1 N4 78.1(3) . . . 2 ? C11 N4 Ca1 N1 -173.2(3) . . . . ? C7 N4 Ca1 N1 4.2(3) . . . . ? C11 N4 Ca1 N1 28.2(3) . . . 2 ? C7 N4 Ca1 N1 -154.4(3) . . . 2 ? C11 N4 Ca1 N5 -39.3(4) . . . 2 ? C7 N4 Ca1 N5 138.1(3) . . . 2 ? C11 N4 Ca1 N5 109.3(3) . . . . ? C7 N4 Ca1 N5 -73.3(3) . . . . ? C1 N1 Ca1 N7 -46.2(3) . . . . ? C5 N1 Ca1 N7 126.2(3) . . . . ? C1 N1 Ca1 N2 178.9(4) . . . . ? C5 N1 Ca1 N2 -8.7(3) . . . . ? C1 N1 Ca1 N2 66.1(4) . . . 2 ? C5 N1 Ca1 N2 -121.5(3) . . . 2 ? C1 N1 Ca1 N4 101.7(4) . . . 2 ? C5 N1 Ca1 N4 -85.9(3) . . . 2 ? C1 N1 Ca1 N4 173.9(3) . . . . ? C5 N1 Ca1 N4 -13.7(3) . . . . ? C1 N1 Ca1 N1 -46.2(3) . . . 2 ? C5 N1 Ca1 N1 126.2(3) . . . 2 ? C1 N1 Ca1 N5 17.5(4) . . . 2 ? C5 N1 Ca1 N5 -170.1(3) . . . 2 ? C1 N1 Ca1 N5 -109.0(4) . . . . ? C5 N1 Ca1 N5 63.5(3) . . . . ? C16 N5 Ca1 N7 -11.4(3) . . . . ? C12 N5 Ca1 N7 176.7(4) . . . . ? C16 N5 Ca1 N2 125.3(3) . . . . ? C12 N5 Ca1 N2 -46.5(4) . . . . ? C16 N5 Ca1 N2 -112.5(3) . . . 2 ? C12 N5 Ca1 N2 75.7(4) . . . 2 ? C16 N5 Ca1 N4 129.7(3) . . . 2 ? C12 N5 Ca1 N4 -42.1(4) . . . 2 ? C16 N5 Ca1 N4 -171.2(3) . . . . ? C12 N5 Ca1 N4 17.0(4) . . . . ? C16 N5 Ca1 N1 62.4(3) . . . . ? C12 N5 Ca1 N1 -109.4(4) . . . . ? C16 N5 Ca1 N1 -87.1(3) . . . 2 ? C12 N5 Ca1 N1 101.1(4) . . . 2 ? C16 N5 Ca1 N5 -11.4(3) . . . 2 ? C12 N5 Ca1 N5 176.7(4) . . . 2 ? 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 H3N O3 0.88 2.40 3.086(5) 134.5 . N3 H3N O1 0.88 2.47 3.039(5) 123.1 2_655 _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.669 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.082 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 0.031 0.010 7.8 0.2 2 0.000 0.339 0.250 94.5 14.4 3 0.000 0.031 0.490 7.5 0.2 4 0.000 0.958 0.514 4.6 -0.1 5 0.000 0.661 0.750 94.5 14.5 6 0.000 0.958 0.986 4.3 0.0 7 0.500 0.839 0.250 94.5 14.4 8 0.500 0.161 0.750 94.5 14.5 9 0.500 0.531 0.010 7.8 0.2 10 0.500 0.531 0.490 7.5 0.2 11 0.500 0.458 0.514 4.6 -0.1 12 0.500 0.458 0.986 4.3 0.0 _platon_squeeze_details ; The residual electron density was assigned to half a molecule of the acetonitrile solvent [59/8 = 7 e par asymmetric unit, half a molecule of CH3CN would give 11e]. ; _database_code_depnum_ccdc_archive 'CCDC 971155' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_jmlgv130325 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C52 H44 Ca2 N12 O6, 3(C2 H3 N), 2(H2 O)' _chemical_formula_sum 'C58 H57 Ca2 N15 O8' _chemical_formula_weight 1172.35 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' Ca Ca 0.2262 0.3064 '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 12.8935(13) _cell_length_b 14.4392(14) _cell_length_c 18.0468(18) _cell_angle_alpha 92.810(2) _cell_angle_beta 107.021(2) _cell_angle_gamma 114.714(2) _cell_volume 2861.0(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5782 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 27.89 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1228 _exptl_absorpt_coefficient_mu 0.268 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9287 _exptl_absorpt_correction_T_max 0.9685 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 45853 _diffrn_reflns_av_R_equivalents 0.1661 _diffrn_reflns_av_sigmaI/netI 0.2662 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 28.18 _reflns_number_total 13395 _reflns_number_gt 5572 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^ > 2\s(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^)+(0.0155P)^2^+6.4825P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 13395 _refine_ls_number_parameters 751 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2651 _refine_ls_R_factor_gt 0.1083 _refine_ls_wR_factor_ref 0.1647 _refine_ls_wR_factor_gt 0.1285 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _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 1.2451(5) 1.1669(4) 0.7840(3) 0.0341(15) Uani 1 1 d . . . H1 H 1.2142 1.1673 0.8257 0.041 Uiso 1 1 calc R . . C2 C 1.3606(5) 1.2436(5) 0.7940(4) 0.0396(16) Uani 1 1 d . . . H2 H 1.4076 1.2945 0.8415 0.048 Uiso 1 1 calc R . . C3 C 1.4055(5) 1.2443(4) 0.7333(4) 0.0363(16) Uani 1 1 d . . . H3 H 1.4833 1.2970 0.7375 0.044 Uiso 1 1 calc R . . C4 C 1.3355(5) 1.1669(4) 0.6665(3) 0.0281(14) Uani 1 1 d . . . H4 H 1.3651 1.1649 0.6243 0.034 Uiso 1 1 calc R . . C5 C 1.2222(5) 1.0927(4) 0.6616(3) 0.0222(13) Uani 1 1 d . . . C6 C 1.1471(5) 1.0106(4) 0.5921(3) 0.0244(13) Uani 1 1 d . . . H6 H 1.1742 1.0104 0.5485 0.029 Uiso 1 1 calc R . . C7 C 0.8666(5) 0.8040(4) 0.5209(3) 0.0228(13) Uani 1 1 d . . . C8 C 0.7873(5) 0.7121(4) 0.4551(3) 0.0257(13) Uani 1 1 d . . . C9 C 0.8288(6) 0.6828(5) 0.3992(3) 0.0415(17) Uani 1 1 d . . . H9 H 0.9113 0.7213 0.4030 0.050 Uiso 1 1 calc R . . C10 C 0.7509(8) 0.5981(5) 0.3383(4) 0.056(2) Uani 1 1 d . . . H10 H 0.7800 0.5792 0.3003 0.068 Uiso 1 1 calc R . . C11 C 0.6316(8) 0.5409(5) 0.3321(4) 0.063(2) Uani 1 1 d . . . H11 H 0.5783 0.4828 0.2899 0.075 Uiso 1 1 calc R . . C12 C 0.5901(6) 0.5682(5) 0.3873(4) 0.052(2) Uani 1 1 d . . . H12 H 0.5079 0.5286 0.3834 0.063 Uiso 1 1 calc R . . C13 C 0.6672(6) 0.6529(4) 0.4484(4) 0.0361(16) Uani 1 1 d . . . H13 H 0.6374 0.6708 0.4863 0.043 Uiso 1 1 calc R . . C14 C 1.0300(5) 0.7577(4) 0.7177(3) 0.0339(15) Uani 1 1 d . . . H14 H 1.0074 0.7482 0.6618 0.041 Uiso 1 1 calc R . . C15 C 1.0634(5) 0.6878(4) 0.7544(4) 0.0371(16) Uani 1 1 d . . . H15 H 1.0650 0.6325 0.7247 0.044 Uiso 1 1 calc R . . C16 C 1.0940(5) 0.7000(4) 0.8343(4) 0.0361(16) Uani 1 1 d . . . H16 H 1.1165 0.6526 0.8611 0.043 Uiso 1 1 calc R . . C17 C 1.0922(5) 0.7812(4) 0.8763(3) 0.0334(15) Uani 1 1 d . . . H17 H 1.1140 0.7909 0.9322 0.040 Uiso 1 1 calc R . . C18 C 1.0578(5) 0.8488(4) 0.8351(3) 0.0241(13) Uani 1 1 d . . . C19 C 1.0539(5) 0.9361(4) 0.8766(3) 0.0308(14) Uani 1 1 d . . . H19 H 1.0785 0.9502 0.9326 0.037 Uiso 1 1 calc R . . C20 C 0.9635(5) 1.1202(4) 0.8277(3) 0.0224(13) Uani 1 1 d . . . C21 C 0.9760(5) 1.2228(4) 0.8613(3) 0.0251(13) Uani 1 1 d . . . C22 C 1.0046(5) 1.2549(4) 0.9412(3) 0.0344(15) Uani 1 1 d . . . H22 H 1.0121 1.2096 0.9767 0.041 Uiso 1 1 calc R . . C23 C 1.0222(6) 1.3531(5) 0.9695(4) 0.0441(17) Uani 1 1 d . . . H23 H 1.0418 1.3750 1.0244 0.053 Uiso 1 1 calc R . . C24 C 1.0115(6) 1.4195(5) 0.9185(4) 0.0448(17) Uani 1 1 d . . . H24 H 1.0247 1.4870 0.9385 0.054 Uiso 1 1 calc R . . C25 C 0.9820(5) 1.3881(4) 0.8389(4) 0.0391(16) Uani 1 1 d . . . H25 H 0.9748 1.4338 0.8037 0.047 Uiso 1 1 calc R . . C26 C 0.9625(5) 1.2887(4) 0.8102(3) 0.0336(15) Uani 1 1 d . . . H26 H 0.9398 1.2659 0.7550 0.040 Uiso 1 1 calc R . . C27 C 0.6693(5) 1.1990(4) 0.7983(3) 0.0307(14) Uani 1 1 d . . . H27 H 0.6677 1.2253 0.7510 0.037 Uiso 1 1 calc R . . C28 C 0.6664(5) 1.2564(4) 0.8605(3) 0.0333(15) Uani 1 1 d . . . H28 H 0.6663 1.3217 0.8564 0.040 Uiso 1 1 calc R . . C29 C 0.6636(5) 1.2179(4) 0.9277(3) 0.0349(15) Uani 1 1 d . . . H29 H 0.6584 1.2546 0.9705 0.042 Uiso 1 1 calc R . . C30 C 0.6687(5) 1.1247(4) 0.9324(3) 0.0302(14) Uani 1 1 d . . . H30 H 0.6676 1.0964 0.9787 0.036 Uiso 1 1 calc R . . C31 C 0.6753(5) 1.0731(4) 0.8687(3) 0.0216(13) Uani 1 1 d . . . C32 C 0.6887(5) 0.9781(4) 0.8743(3) 0.0264(13) Uani 1 1 d . . . H32 H 0.6887 0.9494 0.9206 0.032 Uiso 1 1 calc R . . C33 C 0.7355(5) 0.8109(4) 0.7652(3) 0.0225(13) Uani 1 1 d . . . C34 C 0.7373(5) 0.7074(4) 0.7627(3) 0.0240(13) Uani 1 1 d . . . C35 C 0.7354(5) 0.6558(4) 0.8254(4) 0.0371(16) Uani 1 1 d . . . H35 H 0.7342 0.6865 0.8727 0.045 Uiso 1 1 calc R . . C36 C 0.7353(6) 0.5599(5) 0.8196(4) 0.0451(17) Uani 1 1 d . . . H36 H 0.7334 0.5247 0.8627 0.054 Uiso 1 1 calc R . . C37 C 0.7381(5) 0.5153(5) 0.7517(4) 0.0419(17) Uani 1 1 d . . . H37 H 0.7385 0.4496 0.7479 0.050 Uiso 1 1 calc R . . C38 C 0.7402(5) 0.5656(4) 0.6895(4) 0.0399(16) Uani 1 1 d . . . H38 H 0.7421 0.5345 0.6426 0.048 Uiso 1 1 calc R . . C39 C 0.7397(5) 0.6615(4) 0.6944(3) 0.0324(14) Uani 1 1 d . . . H39 H 0.7411 0.6958 0.6509 0.039 Uiso 1 1 calc R . . C40 C 0.4170(5) 0.7784(4) 0.6868(3) 0.0308(14) Uani 1 1 d . . . H40 H 0.4752 0.7635 0.7233 0.037 Uiso 1 1 calc R . . C41 C 0.2968(5) 0.7067(4) 0.6641(3) 0.0340(15) Uani 1 1 d . . . H41 H 0.2734 0.6441 0.6840 0.041 Uiso 1 1 calc R . . C42 C 0.2116(5) 0.7273(4) 0.6123(3) 0.0312(14) Uani 1 1 d . . . H42 H 0.1276 0.6798 0.5958 0.037 Uiso 1 1 calc R . . C43 C 0.2506(5) 0.8187(4) 0.5844(3) 0.0267(13) Uani 1 1 d . . . H43 H 0.1932 0.8345 0.5481 0.032 Uiso 1 1 calc R . . C44 C 0.3725(5) 0.8868(4) 0.6094(3) 0.0221(13) Uani 1 1 d . . . C45 C 0.4157(5) 0.9829(4) 0.5802(3) 0.0239(13) Uani 1 1 d . . . H45 H 0.3595 0.9992 0.5431 0.029 Uiso 1 1 calc R . . C46 C 0.6861(5) 1.1848(4) 0.5964(3) 0.0195(12) Uani 1 1 d . . . C47 C 0.7399(5) 1.2883(4) 0.5745(3) 0.0242(13) Uani 1 1 d . . . C48 C 0.6710(5) 1.3314(4) 0.5301(3) 0.0311(14) Uani 1 1 d . . . H48 H 0.5847 1.2956 0.5132 0.037 Uiso 1 1 calc R . . C49 C 0.7282(7) 1.4275(5) 0.5104(3) 0.0407(17) Uani 1 1 d . . . H49 H 0.6803 1.4562 0.4792 0.049 Uiso 1 1 calc R . . C50 C 0.8529(6) 1.4813(5) 0.5354(4) 0.0428(17) Uani 1 1 d . . . H50 H 0.8906 1.5469 0.5216 0.051 Uiso 1 1 calc R . . C51 C 0.9228(6) 1.4403(4) 0.5802(4) 0.0399(16) Uani 1 1 d . . . H51 H 1.0091 1.4773 0.5980 0.048 Uiso 1 1 calc R . . C52 C 0.8660(5) 1.3444(4) 0.5991(3) 0.0308(14) Uani 1 1 d . . . H52 H 0.9146 1.3160 0.6298 0.037 Uiso 1 1 calc R . . C53 C 0.6119(6) 0.0926(5) 0.1423(4) 0.0414(17) Uani 1 1 d . . . C54 C 0.6472(6) 0.0361(5) 0.2013(4) 0.0485(18) Uani 1 1 d . . . H54A H 0.5784 -0.0037 0.2182 0.073 Uiso 1 1 calc R . . H54B H 0.7161 0.0854 0.2469 0.073 Uiso 1 1 calc R . . H54C H 0.6709 -0.0116 0.1783 0.073 Uiso 1 1 calc R . . C55 C 0.6438(8) 0.3875(6) 0.1521(4) 0.053(2) Uani 1 1 d . . . C56 C 0.5143(6) 0.3350(6) 0.1113(4) 0.070(2) Uani 1 1 d . . . H56A H 0.4815 0.3853 0.1098 0.105 Uiso 1 1 calc R . . H56B H 0.4763 0.2811 0.1391 0.105 Uiso 1 1 calc R . . H56C H 0.4971 0.3029 0.0572 0.105 Uiso 1 1 calc R . . C57 C 0.6479(6) 0.5144(6) 0.0058(5) 0.0513(19) Uani 1 1 d . . . C58 C 0.7035(6) 0.6036(5) 0.0695(4) 0.059(2) Uani 1 1 d . . . H58A H 0.6502 0.5942 0.1005 0.088 Uiso 1 1 calc R . . H58B H 0.7158 0.6665 0.0474 0.088 Uiso 1 1 calc R . . H58C H 0.7821 0.6106 0.1036 0.088 Uiso 1 1 calc R . . N1 N 1.1752(4) 1.0928(3) 0.7199(3) 0.0253(11) Uani 1 1 d . . . N2 N 1.0446(4) 0.9384(3) 0.5890(2) 0.0208(10) Uani 1 1 d . . . N3 N 0.9796(4) 0.8607(3) 0.5217(2) 0.0225(10) Uani 1 1 d . . . N4 N 1.0278(4) 0.8374(3) 0.7560(3) 0.0257(11) Uani 1 1 d . . . N5 N 1.0166(4) 0.9933(3) 0.8355(3) 0.0259(11) Uani 1 1 d . . . N6 N 1.0201(4) 1.0785(3) 0.8775(3) 0.0279(11) Uani 1 1 d . . . N7 N 0.6742(4) 1.1086(3) 0.8011(3) 0.0248(11) Uani 1 1 d . . . N8 N 0.7005(4) 0.9336(3) 0.8161(2) 0.0226(11) Uani 1 1 d . . . N9 N 0.7116(4) 0.8427(3) 0.8259(2) 0.0242(11) Uani 1 1 d . . . N10 N 0.4578(4) 0.8674(3) 0.6613(3) 0.0249(11) Uani 1 1 d . . . N11 N 0.5293(4) 1.0456(3) 0.6044(2) 0.0218(10) Uani 1 1 d . . . N12 N 0.5647(4) 1.1373(3) 0.5753(2) 0.0209(10) Uani 1 1 d . . . N13 N 0.5833(5) 0.1362(5) 0.0968(4) 0.0601(17) Uani 1 1 d . . . N14 N 0.7471(6) 0.4309(5) 0.1857(4) 0.0651(19) Uani 1 1 d . . . N15 N 0.6040(6) 0.4440(5) -0.0430(4) 0.0701(19) Uani 1 1 d . . . O1 O 0.8221(3) 0.8235(3) 0.5700(2) 0.0259(9) Uani 1 1 d . . . O2 O 0.9056(3) 1.0844(3) 0.7539(2) 0.0215(8) Uani 1 1 d . . . O3 O 0.7542(3) 0.8592(3) 0.7095(2) 0.0228(9) Uani 1 1 d . . . O4 O 0.7565(3) 1.1488(3) 0.6316(2) 0.0252(9) Uani 1 1 d . . . O5 O 0.9186(3) 1.0769(3) 0.6010(2) 0.0309(10) Uani 1 1 d . . . O6 O 0.6362(3) 0.8921(3) 0.5625(2) 0.0295(9) Uani 1 1 d . . . O7 O 0.2395(3) 0.1806(3) 1.0075(2) 0.0409(11) Uani 1 1 d . . . O8 O 0.3691(5) 0.0963(5) 0.9489(3) 0.0950(19) Uani 1 1 d . . . Ca1 Ca 0.94717(10) 0.95874(8) 0.68688(6) 0.0214(3) Uani 1 1 d . . . Ca2 Ca 0.68547(10) 0.99677(8) 0.68880(6) 0.0206(3) Uani 1 1 d . . . H1O5 H 0.8805 1.1095 0.6151 0.050 Uiso 1 1 d . . . H2O5 H 0.9363 1.0852 0.5604 0.050 Uiso 1 1 d . . . H1O6 H 0.6802 0.8512 0.5706 0.050 Uiso 1 1 d . . . H2O6 H 0.5761 0.8885 0.5208 0.050 Uiso 1 1 d . . . H1O7 H 0.1616 0.1415 0.9882 0.050 Uiso 1 1 d . . . H2O7 H 0.2587 0.1825 1.0579 0.050 Uiso 1 1 d . . . H1O8 H 0.3274 0.1215 0.9681 0.050 Uiso 1 1 d . . . H2O8 H 0.4300 0.1003 0.9884 0.050 Uiso 1 1 d . . . 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 0.035(4) 0.039(4) 0.032(4) 0.006(3) 0.013(3) 0.019(3) C2 0.029(4) 0.033(4) 0.044(4) -0.003(3) 0.004(3) 0.009(3) C3 0.027(4) 0.030(4) 0.052(4) 0.012(3) 0.009(3) 0.015(3) C4 0.031(4) 0.031(3) 0.028(4) 0.012(3) 0.013(3) 0.017(3) C5 0.022(3) 0.022(3) 0.026(3) 0.010(3) 0.007(3) 0.013(3) C6 0.025(4) 0.030(3) 0.030(4) 0.011(3) 0.015(3) 0.019(3) C7 0.028(4) 0.023(3) 0.024(3) 0.008(3) 0.009(3) 0.017(3) C8 0.030(4) 0.023(3) 0.026(3) 0.008(3) 0.004(3) 0.017(3) C9 0.052(5) 0.037(4) 0.037(4) 0.003(3) 0.011(4) 0.024(4) C10 0.084(6) 0.047(5) 0.033(4) -0.006(4) 0.007(4) 0.035(5) C11 0.083(7) 0.034(4) 0.044(5) -0.003(4) -0.012(5) 0.026(5) C12 0.044(5) 0.029(4) 0.065(5) 0.010(4) 0.000(4) 0.013(4) C13 0.038(4) 0.027(4) 0.035(4) 0.008(3) 0.000(3) 0.016(3) C14 0.038(4) 0.041(4) 0.031(4) 0.006(3) 0.016(3) 0.023(3) C15 0.046(4) 0.033(4) 0.046(4) 0.010(3) 0.021(4) 0.027(3) C16 0.042(4) 0.036(4) 0.046(4) 0.021(3) 0.019(3) 0.028(3) C17 0.039(4) 0.041(4) 0.029(4) 0.012(3) 0.011(3) 0.026(3) C18 0.018(3) 0.030(3) 0.025(3) 0.006(3) 0.007(3) 0.012(3) C19 0.033(4) 0.044(4) 0.020(3) 0.008(3) 0.008(3) 0.022(3) C20 0.020(3) 0.028(3) 0.023(3) 0.008(3) 0.011(3) 0.011(3) C21 0.020(3) 0.033(3) 0.021(3) 0.002(3) 0.006(3) 0.012(3) C22 0.042(4) 0.042(4) 0.033(4) 0.015(3) 0.017(3) 0.029(3) C23 0.058(5) 0.047(4) 0.036(4) -0.001(3) 0.019(4) 0.031(4) C24 0.060(5) 0.036(4) 0.056(5) 0.012(3) 0.026(4) 0.033(4) C25 0.052(4) 0.034(4) 0.044(4) 0.016(3) 0.024(4) 0.024(3) C26 0.038(4) 0.035(4) 0.033(4) 0.008(3) 0.014(3) 0.019(3) C27 0.037(4) 0.036(4) 0.029(4) 0.014(3) 0.016(3) 0.022(3) C28 0.043(4) 0.028(3) 0.040(4) 0.008(3) 0.016(3) 0.026(3) C29 0.037(4) 0.043(4) 0.033(4) 0.005(3) 0.016(3) 0.022(3) C30 0.037(4) 0.040(4) 0.026(3) 0.013(3) 0.017(3) 0.024(3) C31 0.021(3) 0.030(3) 0.021(3) 0.013(3) 0.010(3) 0.015(3) C32 0.035(4) 0.034(3) 0.024(3) 0.019(3) 0.020(3) 0.020(3) C33 0.017(3) 0.026(3) 0.027(3) 0.009(3) 0.009(3) 0.010(3) C34 0.020(3) 0.027(3) 0.029(3) 0.011(3) 0.013(3) 0.012(3) C35 0.052(4) 0.039(4) 0.041(4) 0.020(3) 0.027(3) 0.031(4) C36 0.065(5) 0.041(4) 0.050(4) 0.027(3) 0.030(4) 0.035(4) C37 0.047(4) 0.025(4) 0.066(5) 0.015(3) 0.029(4) 0.021(3) C38 0.045(4) 0.029(4) 0.053(4) 0.007(3) 0.029(4) 0.015(3) C39 0.035(4) 0.032(4) 0.034(4) 0.012(3) 0.019(3) 0.013(3) C40 0.034(4) 0.032(4) 0.032(4) 0.013(3) 0.009(3) 0.020(3) C41 0.037(4) 0.027(4) 0.040(4) 0.011(3) 0.021(3) 0.011(3) C42 0.021(3) 0.029(4) 0.035(4) -0.002(3) 0.010(3) 0.005(3) C43 0.022(4) 0.031(3) 0.029(3) 0.004(3) 0.008(3) 0.014(3) C44 0.026(4) 0.031(3) 0.021(3) 0.008(3) 0.014(3) 0.019(3) C45 0.024(4) 0.034(3) 0.021(3) 0.009(3) 0.007(3) 0.020(3) C46 0.033(4) 0.020(3) 0.011(3) 0.006(2) 0.011(3) 0.015(3) C47 0.033(4) 0.023(3) 0.020(3) 0.004(3) 0.012(3) 0.014(3) C48 0.040(4) 0.030(3) 0.035(4) 0.013(3) 0.017(3) 0.021(3) C49 0.074(5) 0.034(4) 0.034(4) 0.018(3) 0.025(4) 0.036(4) C50 0.063(5) 0.024(4) 0.047(4) 0.015(3) 0.031(4) 0.016(4) C51 0.046(4) 0.027(4) 0.042(4) 0.007(3) 0.021(4) 0.009(3) C52 0.037(4) 0.030(4) 0.031(4) 0.013(3) 0.015(3) 0.017(3) C53 0.029(4) 0.047(4) 0.049(5) 0.002(4) 0.019(4) 0.015(4) C54 0.043(4) 0.062(5) 0.046(4) 0.010(4) 0.013(4) 0.030(4) C55 0.065(6) 0.057(5) 0.050(5) 0.022(4) 0.029(5) 0.033(5) C56 0.050(5) 0.077(6) 0.079(6) 0.019(5) 0.021(5) 0.025(5) C57 0.044(5) 0.050(5) 0.056(5) 0.010(4) 0.019(4) 0.016(4) C58 0.051(5) 0.051(5) 0.067(5) 0.004(4) 0.019(4) 0.018(4) N1 0.024(3) 0.027(3) 0.025(3) 0.005(2) 0.007(2) 0.013(2) N2 0.024(3) 0.026(3) 0.020(3) 0.006(2) 0.010(2) 0.017(2) N3 0.024(3) 0.026(3) 0.018(3) 0.003(2) 0.006(2) 0.013(2) N4 0.027(3) 0.031(3) 0.026(3) 0.008(2) 0.012(2) 0.018(2) N5 0.027(3) 0.031(3) 0.028(3) 0.007(2) 0.012(2) 0.018(2) N6 0.032(3) 0.031(3) 0.027(3) 0.007(2) 0.009(2) 0.021(3) N7 0.023(3) 0.032(3) 0.029(3) 0.013(2) 0.012(2) 0.019(2) N8 0.025(3) 0.030(3) 0.019(3) 0.010(2) 0.009(2) 0.016(2) N9 0.033(3) 0.029(3) 0.025(3) 0.015(2) 0.016(2) 0.022(2) N10 0.028(3) 0.024(3) 0.029(3) 0.010(2) 0.015(2) 0.013(2) N11 0.029(3) 0.028(3) 0.020(3) 0.010(2) 0.013(2) 0.020(2) N12 0.024(3) 0.024(3) 0.023(3) 0.010(2) 0.009(2) 0.017(2) N13 0.054(4) 0.075(5) 0.070(5) 0.030(4) 0.030(4) 0.039(4) N14 0.066(5) 0.062(5) 0.074(5) 0.018(4) 0.026(4) 0.034(4) N15 0.073(5) 0.062(5) 0.063(5) 0.001(4) 0.029(4) 0.016(4) O1 0.022(2) 0.032(2) 0.025(2) 0.0046(18) 0.0110(18) 0.0113(19) O2 0.022(2) 0.027(2) 0.016(2) 0.0036(17) 0.0042(18) 0.0133(18) O3 0.026(2) 0.026(2) 0.024(2) 0.0116(18) 0.0124(18) 0.0157(19) O4 0.026(2) 0.031(2) 0.027(2) 0.0156(18) 0.0084(18) 0.0190(19) O5 0.043(3) 0.046(3) 0.028(2) 0.0176(19) 0.023(2) 0.034(2) O6 0.033(2) 0.043(2) 0.022(2) 0.0108(19) 0.0060(19) 0.028(2) O7 0.040(3) 0.050(3) 0.033(2) 0.009(2) 0.010(2) 0.023(2) O8 0.104(5) 0.167(6) 0.053(4) 0.018(4) 0.026(3) 0.098(5) Ca1 0.0243(7) 0.0278(7) 0.0220(6) 0.0093(5) 0.0116(5) 0.0177(6) Ca2 0.0237(7) 0.0263(7) 0.0219(6) 0.0119(5) 0.0110(5) 0.0177(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.325(7) . ? C1 C2 1.386(8) . ? C1 H1 0.9500 . ? C2 C3 1.380(8) . ? C2 H2 0.9500 . ? C3 C4 1.380(7) . ? C3 H3 0.9500 . ? C4 C5 1.377(7) . ? C4 H4 0.9500 . ? C5 N1 1.360(6) . ? C5 C6 1.448(7) . ? C6 N2 1.279(6) . ? C6 H6 0.9500 . ? C7 O1 1.267(6) . ? C7 N3 1.335(6) . ? C7 C8 1.489(7) . ? C8 C13 1.384(7) . ? C8 C9 1.395(7) . ? C9 C10 1.380(8) . ? C9 H9 0.9500 . ? C10 C11 1.374(10) . ? C10 H10 0.9500 . ? C11 C12 1.372(9) . ? C11 H11 0.9500 . ? C12 C13 1.382(8) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 N4 1.329(6) . ? C14 C15 1.380(7) . ? C14 H14 0.9500 . ? C15 C16 1.360(7) . ? C15 H15 0.9500 . ? C16 C17 1.376(7) . ? C16 H16 0.9500 . ? C17 C18 1.394(7) . ? C17 H17 0.9500 . ? C18 N4 1.348(6) . ? C18 C19 1.460(7) . ? C19 N5 1.285(6) . ? C19 H19 0.9500 . ? C20 O2 1.275(6) . ? C20 N6 1.319(6) . ? C20 C21 1.497(7) . ? C21 C22 1.383(7) . ? C21 C26 1.384(7) . ? C22 C23 1.383(7) . ? C22 H22 0.9500 . ? C23 C24 1.382(8) . ? C23 H23 0.9500 . ? C24 C25 1.373(8) . ? C24 H24 0.9500 . ? C25 C26 1.394(7) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 N7 1.336(6) . ? C27 C28 1.380(7) . ? C27 H27 0.9500 . ? C28 C29 1.363(7) . ? C28 H28 0.9500 . ? C29 C30 1.380(7) . ? C29 H29 0.9500 . ? C30 C31 1.381(7) . ? C30 H30 0.9500 . ? C31 N7 1.346(6) . ? C31 C32 1.457(7) . ? C32 N8 1.285(6) . ? C32 H32 0.9500 . ? C33 O3 1.274(6) . ? C33 N9 1.331(6) . ? C33 C34 1.503(7) . ? C34 C39 1.385(7) . ? C34 C35 1.386(7) . ? C35 C36 1.383(7) . ? C35 H35 0.9500 . ? C36 C37 1.373(8) . ? C36 H36 0.9500 . ? C37 C38 1.366(8) . ? C37 H37 0.9500 . ? C38 C39 1.386(7) . ? C38 H38 0.9500 . ? C39 H39 0.9500 . ? C40 N10 1.332(6) . ? C40 C41 1.373(7) . ? C40 H40 0.9500 . ? C41 C42 1.367(7) . ? C41 H41 0.9500 . ? C42 C43 1.380(7) . ? C42 H42 0.9500 . ? C43 C44 1.375(7) . ? C43 H43 0.9500 . ? C44 N10 1.358(6) . ? C44 C45 1.453(7) . ? C45 N11 1.278(6) . ? C45 H45 0.9500 . ? C46 O4 1.260(5) . ? C46 N12 1.339(6) . ? C46 C47 1.490(7) . ? C47 C48 1.384(7) . ? C47 C52 1.392(7) . ? C48 C49 1.393(7) . ? C48 H48 0.9500 . ? C49 C50 1.374(8) . ? C49 H49 0.9500 . ? C50 C51 1.373(8) . ? C50 H50 0.9500 . ? C51 C52 1.384(7) . ? C51 H51 0.9500 . ? C52 H52 0.9500 . ? C53 N13 1.129(7) . ? C53 C54 1.456(8) . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C54 H54C 0.9800 . ? C55 N14 1.151(8) . ? C55 C56 1.439(10) . ? C56 H56A 0.9800 . ? C56 H56B 0.9800 . ? C56 H56C 0.9800 . ? C57 N15 1.127(8) . ? C57 C58 1.447(9) . ? C58 H58A 0.9800 . ? C58 H58B 0.9800 . ? C58 H58C 0.9800 . ? N1 Ca1 2.617(5) . ? N2 N3 1.386(5) . ? N2 Ca1 2.518(4) . ? N4 Ca1 2.585(4) . ? N5 N6 1.389(5) . ? N5 Ca1 2.517(4) . ? N7 Ca2 2.603(4) . ? N8 N9 1.394(5) . ? N8 Ca2 2.497(4) . ? N10 Ca2 2.613(4) . ? N11 N12 1.392(5) . ? N11 Ca2 2.523(4) . ? O1 Ca1 2.415(4) . ? O2 Ca2 2.436(4) . ? O2 Ca1 2.454(3) . ? O3 Ca1 2.467(4) . ? O3 Ca2 2.494(3) . ? O4 Ca2 2.412(3) . ? O5 Ca1 2.429(3) . ? O5 H1O5 0.8845 . ? O5 H2O5 0.8288 . ? O6 Ca2 2.427(4) . ? O6 H1O6 0.9665 . ? O6 H2O6 0.8887 . ? O7 H1O7 0.8671 . ? O7 H2O7 0.8642 . ? O8 H1O8 0.8950 . ? O8 H2O8 0.8708 . ? 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 124.1(6) . . ? N1 C1 H1 118.0 . . ? C2 C1 H1 118.0 . . ? C3 C2 C1 118.3(6) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? C2 C3 C4 118.8(6) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 119.2(5) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? N1 C5 C4 122.7(5) . . ? N1 C5 C6 117.1(5) . . ? C4 C5 C6 120.3(5) . . ? N2 C6 C5 120.5(5) . . ? N2 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? O1 C7 N3 125.4(5) . . ? O1 C7 C8 118.4(5) . . ? N3 C7 C8 116.1(5) . . ? C13 C8 C9 118.2(6) . . ? C13 C8 C7 119.1(5) . . ? C9 C8 C7 122.7(5) . . ? C10 C9 C8 120.4(6) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C11 C10 C9 120.7(7) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C12 C11 C10 119.4(7) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C11 C12 C13 120.5(7) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C12 C13 C8 120.8(6) . . ? C12 C13 H13 119.6 . . ? C8 C13 H13 119.6 . . ? N4 C14 C15 123.9(5) . . ? N4 C14 H14 118.1 . . ? C15 C14 H14 118.1 . . ? C16 C15 C14 118.2(5) . . ? C16 C15 H15 120.9 . . ? C14 C15 H15 120.9 . . ? C15 C16 C17 119.9(5) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C16 C17 C18 118.6(5) . . ? C16 C17 H17 120.7 . . ? C18 C17 H17 120.7 . . ? N4 C18 C17 121.9(5) . . ? N4 C18 C19 117.1(4) . . ? C17 C18 C19 121.0(5) . . ? N5 C19 C18 118.4(5) . . ? N5 C19 H19 120.8 . . ? C18 C19 H19 120.8 . . ? O2 C20 N6 126.3(5) . . ? O2 C20 C21 117.8(4) . . ? N6 C20 C21 115.8(5) . . ? C22 C21 C26 119.4(5) . . ? C22 C21 C20 122.4(5) . . ? C26 C21 C20 118.2(5) . . ? C21 C22 C23 119.8(5) . . ? C21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? C24 C23 C22 120.5(6) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C25 C24 C23 120.2(6) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C24 C25 C26 119.3(5) . . ? C24 C25 H25 120.3 . . ? C26 C25 H25 120.3 . . ? C21 C26 C25 120.7(5) . . ? C21 C26 H26 119.7 . . ? C25 C26 H26 119.7 . . ? N7 C27 C28 123.7(5) . . ? N7 C27 H27 118.2 . . ? C28 C27 H27 118.2 . . ? C29 C28 C27 119.0(5) . . ? C29 C28 H28 120.5 . . ? C27 C28 H28 120.5 . . ? C28 C29 C30 118.7(5) . . ? C28 C29 H29 120.6 . . ? C30 C29 H29 120.6 . . ? C29 C30 C31 119.1(5) . . ? C29 C30 H30 120.4 . . ? C31 C30 H30 120.4 . . ? N7 C31 C30 122.8(5) . . ? N7 C31 C32 117.1(5) . . ? C30 C31 C32 120.0(5) . . ? N8 C32 C31 119.3(5) . . ? N8 C32 H32 120.3 . . ? C31 C32 H32 120.3 . . ? O3 C33 N9 125.9(5) . . ? O3 C33 C34 118.4(5) . . ? N9 C33 C34 115.7(5) . . ? C39 C34 C35 118.8(5) . . ? C39 C34 C33 118.4(5) . . ? C35 C34 C33 122.8(5) . . ? C36 C35 C34 120.4(6) . . ? C36 C35 H35 119.8 . . ? C34 C35 H35 119.8 . . ? C37 C36 C35 120.2(6) . . ? C37 C36 H36 119.9 . . ? C35 C36 H36 119.9 . . ? C38 C37 C36 119.9(5) . . ? C38 C37 H37 120.1 . . ? C36 C37 H37 120.1 . . ? C37 C38 C39 120.6(6) . . ? C37 C38 H38 119.7 . . ? C39 C38 H38 119.7 . . ? C34 C39 C38 120.1(5) . . ? C34 C39 H39 119.9 . . ? C38 C39 H39 119.9 . . ? N10 C40 C41 124.7(5) . . ? N10 C40 H40 117.7 . . ? C41 C40 H40 117.7 . . ? C42 C41 C40 118.5(5) . . ? C42 C41 H41 120.8 . . ? C40 C41 H41 120.8 . . ? C41 C42 C43 118.4(5) . . ? C41 C42 H42 120.8 . . ? C43 C42 H42 120.8 . . ? C44 C43 C42 120.0(5) . . ? C44 C43 H43 120.0 . . ? C42 C43 H43 120.0 . . ? N10 C44 C43 122.0(5) . . ? N10 C44 C45 117.0(5) . . ? C43 C44 C45 120.9(5) . . ? N11 C45 C44 120.0(5) . . ? N11 C45 H45 120.0 . . ? C44 C45 H45 120.0 . . ? O4 C46 N12 125.5(5) . . ? O4 C46 C47 118.5(5) . . ? N12 C46 C47 116.0(4) . . ? C48 C47 C52 118.0(5) . . ? C48 C47 C46 123.4(5) . . ? C52 C47 C46 118.7(5) . . ? C47 C48 C49 120.0(6) . . ? C47 C48 H48 120.0 . . ? C49 C48 H48 120.0 . . ? C50 C49 C48 120.9(6) . . ? C50 C49 H49 119.5 . . ? C48 C49 H49 119.5 . . ? C51 C50 C49 119.9(6) . . ? C51 C50 H50 120.0 . . ? C49 C50 H50 120.0 . . ? C50 C51 C52 119.1(6) . . ? C50 C51 H51 120.4 . . ? C52 C51 H51 120.4 . . ? C51 C52 C47 122.1(5) . . ? C51 C52 H52 119.0 . . ? C47 C52 H52 119.0 . . ? N13 C53 C54 179.1(7) . . ? C53 C54 H54A 109.5 . . ? C53 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C53 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? N14 C55 C56 178.6(8) . . ? C55 C56 H56A 109.5 . . ? C55 C56 H56B 109.5 . . ? H56A C56 H56B 109.5 . . ? C55 C56 H56C 109.5 . . ? H56A C56 H56C 109.5 . . ? H56B C56 H56C 109.5 . . ? N15 C57 C58 179.0(9) . . ? C57 C58 H58A 109.5 . . ? C57 C58 H58B 109.5 . . ? H58A C58 H58B 109.5 . . ? C57 C58 H58C 109.5 . . ? H58A C58 H58C 109.5 . . ? H58B C58 H58C 109.5 . . ? C1 N1 C5 116.9(5) . . ? C1 N1 Ca1 126.7(4) . . ? C5 N1 Ca1 116.1(3) . . ? C6 N2 N3 117.3(4) . . ? C6 N2 Ca1 120.3(3) . . ? N3 N2 Ca1 121.2(3) . . ? C7 N3 N2 109.4(4) . . ? C14 N4 C18 117.5(4) . . ? C14 N4 Ca1 124.0(4) . . ? C18 N4 Ca1 118.2(3) . . ? C19 N5 N6 116.5(4) . . ? C19 N5 Ca1 122.4(4) . . ? N6 N5 Ca1 121.0(3) . . ? C20 N6 N5 109.0(4) . . ? C27 N7 C31 116.6(5) . . ? C27 N7 Ca2 126.1(4) . . ? C31 N7 Ca2 117.2(3) . . ? C32 N8 N9 115.6(4) . . ? C32 N8 Ca2 122.2(3) . . ? N9 N8 Ca2 122.0(3) . . ? C33 N9 N8 109.3(4) . . ? C40 N10 C44 116.4(5) . . ? C40 N10 Ca2 126.2(4) . . ? C44 N10 Ca2 117.0(3) . . ? C45 N11 N12 117.2(4) . . ? C45 N11 Ca2 121.5(3) . . ? N12 N11 Ca2 120.9(3) . . ? C46 N12 N11 109.1(4) . . ? C7 O1 Ca1 121.4(3) . . ? C20 O2 Ca2 126.6(3) . . ? C20 O2 Ca1 118.5(3) . . ? Ca2 O2 Ca1 96.48(12) . . ? C33 O3 Ca1 129.2(3) . . ? C33 O3 Ca2 117.8(3) . . ? Ca1 O3 Ca2 94.66(12) . . ? C46 O4 Ca2 121.6(3) . . ? Ca1 O5 H1O5 112.8 . . ? Ca1 O5 H2O5 126.8 . . ? H1O5 O5 H2O5 120.3 . . ? Ca2 O6 H1O6 108.7 . . ? Ca2 O6 H2O6 119.6 . . ? H1O6 O6 H2O6 130.8 . . ? H1O7 O7 H2O7 104.9 . . ? H1O8 O8 H2O8 108.2 . . ? O1 Ca1 O5 85.61(12) . . ? O1 Ca1 O2 131.16(12) . . ? O5 Ca1 O2 70.33(11) . . ? O1 Ca1 O3 75.39(12) . . ? O5 Ca1 O3 107.91(12) . . ? O2 Ca1 O3 72.89(11) . . ? O1 Ca1 N5 143.42(14) . . ? O5 Ca1 N5 127.09(13) . . ? O2 Ca1 N5 61.58(12) . . ? O3 Ca1 N5 78.53(13) . . ? O1 Ca1 N2 62.13(13) . . ? O5 Ca1 N2 77.38(12) . . ? O2 Ca1 N2 142.61(13) . . ? O3 Ca1 N2 136.85(14) . . ? N5 Ca1 N2 133.39(14) . . ? O1 Ca1 N4 90.45(13) . . ? O5 Ca1 N4 161.30(13) . . ? O2 Ca1 N4 124.45(13) . . ? O3 Ca1 N4 88.66(12) . . ? N5 Ca1 N4 63.57(14) . . ? N2 Ca1 N4 84.62(13) . . ? O1 Ca1 N1 126.04(13) . . ? O5 Ca1 N1 81.01(13) . . ? O2 Ca1 N1 92.27(13) . . ? O3 Ca1 N1 158.04(13) . . ? N5 Ca1 N1 80.17(14) . . ? N2 Ca1 N1 63.95(14) . . ? N4 Ca1 N1 86.63(14) . . ? O4 Ca2 O6 87.99(12) . . ? O4 Ca2 O2 74.66(11) . . ? O6 Ca2 O2 108.99(12) . . ? O4 Ca2 O3 131.18(12) . . ? O6 Ca2 O3 69.88(11) . . ? O2 Ca2 O3 72.73(11) . . ? O4 Ca2 N8 144.04(14) . . ? O6 Ca2 N8 124.98(13) . . ? O2 Ca2 N8 80.46(13) . . ? O3 Ca2 N8 61.58(12) . . ? O4 Ca2 N11 62.03(13) . . ? O6 Ca2 N11 81.17(12) . . ? O2 Ca2 N11 135.31(14) . . ? O3 Ca2 N11 146.26(14) . . ? N8 Ca2 N11 130.14(14) . . ? O4 Ca2 N7 89.00(13) . . ? O6 Ca2 N7 162.16(12) . . ? O2 Ca2 N7 87.10(12) . . ? O3 Ca2 N7 124.06(12) . . ? N8 Ca2 N7 63.91(13) . . ? N11 Ca2 N7 81.89(13) . . ? O4 Ca2 N10 125.53(13) . . ? O6 Ca2 N10 79.35(13) . . ? O2 Ca2 N10 159.18(13) . . ? O3 Ca2 N10 93.40(12) . . ? N8 Ca2 N10 79.25(14) . . ? N11 Ca2 N10 63.72(14) . . ? N7 Ca2 N10 88.17(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 0.9(9) . . . . ? C1 C2 C3 C4 -2.0(8) . . . . ? C2 C3 C4 C5 1.2(8) . . . . ? C3 C4 C5 N1 0.7(8) . . . . ? C3 C4 C5 C6 -179.9(5) . . . . ? N1 C5 C6 N2 -4.3(7) . . . . ? C4 C5 C6 N2 176.3(5) . . . . ? O1 C7 C8 C13 1.8(7) . . . . ? N3 C7 C8 C13 -176.8(5) . . . . ? O1 C7 C8 C9 -178.4(5) . . . . ? N3 C7 C8 C9 3.0(7) . . . . ? C13 C8 C9 C10 1.2(8) . . . . ? C7 C8 C9 C10 -178.6(5) . . . . ? C8 C9 C10 C11 -0.5(9) . . . . ? C9 C10 C11 C12 -0.3(10) . . . . ? C10 C11 C12 C13 0.4(10) . . . . ? C11 C12 C13 C8 0.3(9) . . . . ? C9 C8 C13 C12 -1.1(8) . . . . ? C7 C8 C13 C12 178.8(5) . . . . ? N4 C14 C15 C16 1.1(9) . . . . ? C14 C15 C16 C17 -0.6(9) . . . . ? C15 C16 C17 C18 0.5(9) . . . . ? C16 C17 C18 N4 -0.8(8) . . . . ? C16 C17 C18 C19 179.9(5) . . . . ? N4 C18 C19 N5 3.5(8) . . . . ? C17 C18 C19 N5 -177.1(5) . . . . ? O2 C20 C21 C22 161.0(5) . . . . ? N6 C20 C21 C22 -22.6(8) . . . . ? O2 C20 C21 C26 -21.4(7) . . . . ? N6 C20 C21 C26 155.1(5) . . . . ? C26 C21 C22 C23 -1.5(8) . . . . ? C20 C21 C22 C23 176.1(5) . . . . ? C21 C22 C23 C24 0.0(9) . . . . ? C22 C23 C24 C25 0.7(10) . . . . ? C23 C24 C25 C26 0.2(9) . . . . ? C22 C21 C26 C25 2.4(8) . . . . ? C20 C21 C26 C25 -175.3(5) . . . . ? C24 C25 C26 C21 -1.8(9) . . . . ? N7 C27 C28 C29 -2.6(9) . . . . ? C27 C28 C29 C30 2.5(9) . . . . ? C28 C29 C30 C31 -0.5(9) . . . . ? C29 C30 C31 N7 -1.5(8) . . . . ? C29 C30 C31 C32 176.0(5) . . . . ? N7 C31 C32 N8 1.0(8) . . . . ? C30 C31 C32 N8 -176.7(5) . . . . ? O3 C33 C34 C39 -10.1(7) . . . . ? N9 C33 C34 C39 168.6(5) . . . . ? O3 C33 C34 C35 170.5(5) . . . . ? N9 C33 C34 C35 -10.8(8) . . . . ? C39 C34 C35 C36 -0.4(9) . . . . ? C33 C34 C35 C36 179.0(5) . . . . ? C34 C35 C36 C37 0.5(10) . . . . ? C35 C36 C37 C38 -0.4(10) . . . . ? C36 C37 C38 C39 0.1(9) . . . . ? C35 C34 C39 C38 0.0(8) . . . . ? C33 C34 C39 C38 -179.4(5) . . . . ? C37 C38 C39 C34 0.1(9) . . . . ? N10 C40 C41 C42 -0.7(9) . . . . ? C40 C41 C42 C43 0.8(8) . . . . ? C41 C42 C43 C44 -0.4(8) . . . . ? C42 C43 C44 N10 -0.1(8) . . . . ? C42 C43 C44 C45 179.4(5) . . . . ? N10 C44 C45 N11 -1.0(7) . . . . ? C43 C44 C45 N11 179.5(5) . . . . ? O4 C46 C47 C48 174.5(5) . . . . ? N12 C46 C47 C48 -4.6(7) . . . . ? O4 C46 C47 C52 -4.9(7) . . . . ? N12 C46 C47 C52 176.0(5) . . . . ? C52 C47 C48 C49 1.0(8) . . . . ? C46 C47 C48 C49 -178.4(5) . . . . ? C47 C48 C49 C50 -1.0(8) . . . . ? C48 C49 C50 C51 0.2(9) . . . . ? C49 C50 C51 C52 0.5(9) . . . . ? C50 C51 C52 C47 -0.4(9) . . . . ? C48 C47 C52 C51 -0.4(8) . . . . ? C46 C47 C52 C51 179.1(5) . . . . ? C2 C1 N1 C5 1.0(8) . . . . ? C2 C1 N1 Ca1 -171.8(4) . . . . ? C4 C5 N1 C1 -1.8(7) . . . . ? C6 C5 N1 C1 178.7(4) . . . . ? C4 C5 N1 Ca1 171.8(4) . . . . ? C6 C5 N1 Ca1 -7.7(5) . . . . ? C5 C6 N2 N3 -178.0(4) . . . . ? C5 C6 N2 Ca1 14.9(6) . . . . ? O1 C7 N3 N2 5.8(7) . . . . ? C8 C7 N3 N2 -175.7(4) . . . . ? C6 N2 N3 C7 -167.9(4) . . . . ? Ca1 N2 N3 C7 -0.9(5) . . . . ? C15 C14 N4 C18 -1.3(8) . . . . ? C15 C14 N4 Ca1 -174.3(4) . . . . ? C17 C18 N4 C14 1.1(8) . . . . ? C19 C18 N4 C14 -179.5(5) . . . . ? C17 C18 N4 Ca1 174.5(4) . . . . ? C19 C18 N4 Ca1 -6.1(6) . . . . ? C18 C19 N5 N6 -176.9(5) . . . . ? C18 C19 N5 Ca1 1.0(7) . . . . ? O2 C20 N6 N5 5.5(7) . . . . ? C21 C20 N6 N5 -170.6(4) . . . . ? C19 N5 N6 C20 -171.2(5) . . . . ? Ca1 N5 N6 C20 10.8(5) . . . . ? C28 C27 N7 C31 0.6(8) . . . . ? C28 C27 N7 Ca2 -178.4(4) . . . . ? C30 C31 N7 C27 1.5(8) . . . . ? C32 C31 N7 C27 -176.1(5) . . . . ? C30 C31 N7 Ca2 -179.4(4) . . . . ? C32 C31 N7 Ca2 3.0(6) . . . . ? C31 C32 N8 N9 -179.4(4) . . . . ? C31 C32 N8 Ca2 -4.8(7) . . . . ? O3 C33 N9 N8 4.7(7) . . . . ? C34 C33 N9 N8 -173.9(4) . . . . ? C32 N8 N9 C33 -173.7(5) . . . . ? Ca2 N8 N9 C33 11.6(5) . . . . ? C41 C40 N10 C44 0.2(8) . . . . ? C41 C40 N10 Ca2 -172.4(4) . . . . ? C43 C44 N10 C40 0.2(7) . . . . ? C45 C44 N10 C40 -179.2(4) . . . . ? C43 C44 N10 Ca2 173.5(4) . . . . ? C45 C44 N10 Ca2 -6.0(6) . . . . ? C44 C45 N11 N12 -178.9(4) . . . . ? C44 C45 N11 Ca2 8.0(6) . . . . ? O4 C46 N12 N11 5.0(7) . . . . ? C47 C46 N12 N11 -176.0(4) . . . . ? C45 N11 N12 C46 -170.1(4) . . . . ? Ca2 N11 N12 C46 3.0(5) . . . . ? N3 C7 O1 Ca1 -8.3(7) . . . . ? C8 C7 O1 Ca1 173.3(3) . . . . ? N6 C20 O2 Ca2 105.0(5) . . . . ? C21 C20 O2 Ca2 -79.0(5) . . . . ? N6 C20 O2 Ca1 -19.3(7) . . . . ? C21 C20 O2 Ca1 156.7(3) . . . . ? N9 C33 O3 Ca1 105.0(5) . . . . ? C34 C33 O3 Ca1 -76.5(6) . . . . ? N9 C33 O3 Ca2 -18.2(7) . . . . ? C34 C33 O3 Ca2 160.2(3) . . . . ? N12 C46 O4 Ca2 -11.2(7) . . . . ? C47 C46 O4 Ca2 169.9(3) . . . . ? C7 O1 Ca1 O5 82.9(4) . . . . ? C7 O1 Ca1 O2 141.9(3) . . . . ? C7 O1 Ca1 O3 -167.3(4) . . . . ? C7 O1 Ca1 N5 -121.4(4) . . . . ? C7 O1 Ca1 N2 4.8(3) . . . . ? C7 O1 Ca1 N4 -78.8(4) . . . . ? C7 O1 Ca1 N1 7.3(4) . . . . ? C20 O2 Ca1 O1 153.7(3) . . . . ? Ca2 O2 Ca1 O1 15.51(19) . . . . ? C20 O2 Ca1 O5 -141.2(4) . . . . ? Ca2 O2 Ca1 O5 80.66(13) . . . . ? C20 O2 Ca1 O3 102.0(4) . . . . ? Ca2 O2 Ca1 O3 -36.20(11) . . . . ? C20 O2 Ca1 N5 16.0(3) . . . . ? Ca2 O2 Ca1 N5 -122.19(16) . . . . ? C20 O2 Ca1 N2 -109.3(4) . . . . ? Ca2 O2 Ca1 N2 112.5(2) . . . . ? C20 O2 Ca1 N4 25.9(4) . . . . ? Ca2 O2 Ca1 N4 -112.26(15) . . . . ? C20 O2 Ca1 N1 -61.5(4) . . . . ? Ca2 O2 Ca1 N1 160.27(12) . . . . ? C33 O3 Ca1 O1 120.6(4) . . . . ? Ca2 O3 Ca1 O1 -107.24(13) . . . . ? C33 O3 Ca1 O5 -159.0(4) . . . . ? Ca2 O3 Ca1 O5 -26.88(15) . . . . ? C33 O3 Ca1 O2 -97.0(4) . . . . ? Ca2 O3 Ca1 O2 35.11(11) . . . . ? C33 O3 Ca1 N5 -33.5(4) . . . . ? Ca2 O3 Ca1 N5 98.65(13) . . . . ? C33 O3 Ca1 N2 110.5(4) . . . . ? Ca2 O3 Ca1 N2 -117.40(16) . . . . ? C33 O3 Ca1 N4 29.8(4) . . . . ? Ca2 O3 Ca1 N4 161.93(13) . . . . ? C33 O3 Ca1 N1 -47.8(6) . . . . ? Ca2 O3 Ca1 N1 84.4(3) . . . . ? C19 N5 Ca1 O1 46.3(5) . . . . ? N6 N5 Ca1 O1 -135.9(3) . . . . ? C19 N5 Ca1 O5 -164.7(4) . . . . ? N6 N5 Ca1 O5 13.1(4) . . . . ? C19 N5 Ca1 O2 168.0(5) . . . . ? N6 N5 Ca1 O2 -14.2(3) . . . . ? C19 N5 Ca1 O3 91.4(4) . . . . ? N6 N5 Ca1 O3 -90.8(4) . . . . ? C19 N5 Ca1 N2 -54.9(5) . . . . ? N6 N5 Ca1 N2 122.8(3) . . . . ? C19 N5 Ca1 N4 -2.8(4) . . . . ? N6 N5 Ca1 N4 175.0(4) . . . . ? C19 N5 Ca1 N1 -93.9(4) . . . . ? N6 N5 Ca1 N1 83.8(4) . . . . ? C6 N2 Ca1 O1 164.8(4) . . . . ? N3 N2 Ca1 O1 -1.9(3) . . . . ? C6 N2 Ca1 O5 73.1(4) . . . . ? N3 N2 Ca1 O5 -93.6(3) . . . . ? C6 N2 Ca1 O2 42.5(5) . . . . ? N3 N2 Ca1 O2 -124.1(3) . . . . ? C6 N2 Ca1 O3 175.9(3) . . . . ? N3 N2 Ca1 O3 9.3(4) . . . . ? C6 N2 Ca1 N5 -56.6(4) . . . . ? N3 N2 Ca1 N5 136.7(3) . . . . ? C6 N2 Ca1 N4 -101.9(4) . . . . ? N3 N2 Ca1 N4 91.5(3) . . . . ? C6 N2 Ca1 N1 -13.0(3) . . . . ? N3 N2 Ca1 N1 -179.6(4) . . . . ? C14 N4 Ca1 O1 24.3(4) . . . . ? C18 N4 Ca1 O1 -148.6(4) . . . . ? C14 N4 Ca1 O5 -53.3(7) . . . . ? C18 N4 Ca1 O5 133.8(5) . . . . ? C14 N4 Ca1 O2 167.8(4) . . . . ? C18 N4 Ca1 O2 -5.2(4) . . . . ? C14 N4 Ca1 O3 99.7(4) . . . . ? C18 N4 Ca1 O3 -73.3(4) . . . . ? C14 N4 Ca1 N5 177.5(5) . . . . ? C18 N4 Ca1 N5 4.6(4) . . . . ? C14 N4 Ca1 N2 -37.7(4) . . . . ? C18 N4 Ca1 N2 149.4(4) . . . . ? C14 N4 Ca1 N1 -101.8(4) . . . . ? C18 N4 Ca1 N1 85.3(4) . . . . ? C1 N1 Ca1 O1 -179.5(4) . . . . ? C5 N1 Ca1 O1 7.7(4) . . . . ? C1 N1 Ca1 O5 102.7(4) . . . . ? C5 N1 Ca1 O5 -70.1(3) . . . . ? C1 N1 Ca1 O2 33.0(4) . . . . ? C5 N1 Ca1 O2 -139.8(3) . . . . ? C1 N1 Ca1 O3 -13.4(6) . . . . ? C5 N1 Ca1 O3 173.7(3) . . . . ? C1 N1 Ca1 N5 -27.6(4) . . . . ? C5 N1 Ca1 N5 159.5(3) . . . . ? C1 N1 Ca1 N2 -177.0(5) . . . . ? C5 N1 Ca1 N2 10.1(3) . . . . ? C1 N1 Ca1 N4 -91.4(4) . . . . ? C5 N1 Ca1 N4 95.8(3) . . . . ? C46 O4 Ca2 O6 89.2(4) . . . . ? C46 O4 Ca2 O2 -160.4(4) . . . . ? C46 O4 Ca2 O3 150.0(3) . . . . ? C46 O4 Ca2 N8 -112.6(4) . . . . ? C46 O4 Ca2 N11 8.2(3) . . . . ? C46 O4 Ca2 N7 -73.2(4) . . . . ? C46 O4 Ca2 N10 13.9(4) . . . . ? C20 O2 Ca2 O4 119.5(4) . . . . ? Ca1 O2 Ca2 O4 -107.36(13) . . . . ? C20 O2 Ca2 O6 -158.1(4) . . . . ? Ca1 O2 Ca2 O6 -25.00(14) . . . . ? C20 O2 Ca2 O3 -97.3(4) . . . . ? Ca1 O2 Ca2 O3 35.79(11) . . . . ? C20 O2 Ca2 N8 -34.2(4) . . . . ? Ca1 O2 Ca2 N8 98.85(13) . . . . ? C20 O2 Ca2 N11 105.2(4) . . . . ? Ca1 O2 Ca2 N11 -121.72(16) . . . . ? C20 O2 Ca2 N7 29.8(4) . . . . ? Ca1 O2 Ca2 N7 162.88(13) . . . . ? C20 O2 Ca2 N10 -47.3(6) . . . . ? Ca1 O2 Ca2 N10 85.8(4) . . . . ? C33 O3 Ca2 O4 154.2(3) . . . . ? Ca1 O3 Ca2 O4 14.8(2) . . . . ? C33 O3 Ca2 O6 -137.5(4) . . . . ? Ca1 O3 Ca2 O6 83.04(13) . . . . ? C33 O3 Ca2 O2 104.0(4) . . . . ? Ca1 O3 Ca2 O2 -35.44(11) . . . . ? C33 O3 Ca2 N8 15.7(3) . . . . ? Ca1 O3 Ca2 N8 -123.77(16) . . . . ? C33 O3 Ca2 N11 -105.0(4) . . . . ? Ca1 O3 Ca2 N11 115.6(2) . . . . ? C33 O3 Ca2 N7 29.9(4) . . . . ? Ca1 O3 Ca2 N7 -109.53(15) . . . . ? C33 O3 Ca2 N10 -60.2(4) . . . . ? Ca1 O3 Ca2 N10 160.39(13) . . . . ? C32 N8 Ca2 O4 49.3(5) . . . . ? N9 N8 Ca2 O4 -136.4(3) . . . . ? C32 N8 Ca2 O6 -157.6(4) . . . . ? N9 N8 Ca2 O6 16.7(4) . . . . ? C32 N8 Ca2 O2 95.8(4) . . . . ? N9 N8 Ca2 O2 -89.9(4) . . . . ? C32 N8 Ca2 O3 171.3(4) . . . . ? N9 N8 Ca2 O3 -14.4(3) . . . . ? C32 N8 Ca2 N11 -47.4(5) . . . . ? N9 N8 Ca2 N11 126.9(3) . . . . ? C32 N8 Ca2 N7 4.4(4) . . . . ? N9 N8 Ca2 N7 178.7(4) . . . . ? C32 N8 Ca2 N10 -88.9(4) . . . . ? N9 N8 Ca2 N10 85.4(4) . . . . ? C45 N11 Ca2 O4 167.1(4) . . . . ? N12 N11 Ca2 O4 -5.6(3) . . . . ? C45 N11 Ca2 O6 74.7(4) . . . . ? N12 N11 Ca2 O6 -98.1(3) . . . . ? C45 N11 Ca2 O2 -177.1(3) . . . . ? N12 N11 Ca2 O2 10.1(4) . . . . ? C45 N11 Ca2 O3 44.0(5) . . . . ? N12 N11 Ca2 O3 -128.8(3) . . . . ? C45 N11 Ca2 N8 -54.2(4) . . . . ? N12 N11 Ca2 N8 133.0(3) . . . . ? C45 N11 Ca2 N7 -99.7(4) . . . . ? N12 N11 Ca2 N7 87.6(3) . . . . ? C45 N11 Ca2 N10 -7.7(4) . . . . ? N12 N11 Ca2 N10 179.5(4) . . . . ? C27 N7 Ca2 O4 19.9(4) . . . . ? C31 N7 Ca2 O4 -159.1(4) . . . . ? C27 N7 Ca2 O6 -60.4(7) . . . . ? C31 N7 Ca2 O6 120.6(5) . . . . ? C27 N7 Ca2 O2 94.6(4) . . . . ? C31 N7 Ca2 O2 -84.4(4) . . . . ? C27 N7 Ca2 O3 161.4(4) . . . . ? C31 N7 Ca2 O3 -17.6(4) . . . . ? C27 N7 Ca2 N8 175.4(5) . . . . ? C31 N7 Ca2 N8 -3.6(3) . . . . ? C27 N7 Ca2 N11 -42.0(4) . . . . ? C31 N7 Ca2 N11 139.0(4) . . . . ? C27 N7 Ca2 N10 -105.7(4) . . . . ? C31 N7 Ca2 N10 75.3(4) . . . . ? C40 N10 Ca2 O4 173.7(4) . . . . ? C44 N10 Ca2 O4 1.1(4) . . . . ? C40 N10 Ca2 O6 93.9(4) . . . . ? C44 N10 Ca2 O6 -78.6(3) . . . . ? C40 N10 Ca2 O2 -22.0(6) . . . . ? C44 N10 Ca2 O2 165.5(3) . . . . ? C40 N10 Ca2 O3 25.1(4) . . . . ? C44 N10 Ca2 O3 -147.4(3) . . . . ? C40 N10 Ca2 N8 -35.1(4) . . . . ? C44 N10 Ca2 N8 152.4(4) . . . . ? C40 N10 Ca2 N11 179.3(5) . . . . ? C44 N10 Ca2 N11 6.7(3) . . . . ? C40 N10 Ca2 N7 -98.9(4) . . . . ? C44 N10 Ca2 N7 88.6(4) . . . . ? 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 O5 H1O5 O4 0.88 2.00 2.861(5) 165.2 . O5 H2O5 N3 0.83 2.08 2.889(5) 165.1 2_776 O6 H1O6 O1 0.97 2.03 2.926(5) 152.8 . O6 H2O6 N12 0.89 1.99 2.877(5) 173.4 2_676 O7 H1O7 N6 0.87 2.11 2.824(6) 139.3 1_445 O7 H2O7 N9 0.86 2.10 2.952(5) 169.5 2_667 O8 H1O8 O7 0.89 1.93 2.828(6) 177.7 . O8 H2O8 N13 0.87 2.19 3.047(8) 169.4 1_556 _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.642 _refine_diff_density_min -0.706 _refine_diff_density_rms 0.086 _database_code_depnum_ccdc_archive 'CCDC 971407'