Electronic Supplementary Material for CrystEngComm This Journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name C.Aakeroy _publ_contact_author_address ; Department of Chemistry Kansas State University Manhattan Manhattan Kansas 66506-3701 UNITED STATES OF AMERICA ; _publ_contact_author_email AAKEROY@KSU.EDU _publ_section_title ; Improving success rate of hydrogen-bond driven synthesis of co-crystals ; loop_ _publ_author_name C.Aakeroy 'John Desper' 'Meg E. Fasulo' # Attachment 'all.cif' data_1a _database_code_depnum_ccdc_archive 'CCDC 607722' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,4-bis[(1-pyrazolyl)methyl]benzene, (3,5-dinitrobenzoic acid)2 ; _chemical_name_common ;1,4-bis((1-pyrazolyl)methyl)benzene, (3,5-dinitrobenzoic acid)2 ; _chemical_melting_point ? _chemical_formula_moiety ; (C14 H14 N4) (C7 H4 N2 O6)2 ; _chemical_formula_sum 'C28 H22 N8 O12' _chemical_formula_weight 662.54 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 12.526(3) _cell_length_b 10.179(2) _cell_length_c 12.332(3) _cell_angle_alpha 90.00 _cell_angle_beta 115.038(4) _cell_angle_gamma 90.00 _cell_volume 1424.6(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4837 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 29.50 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.545 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 684 _exptl_absorpt_coefficient_mu 0.124 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.769 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14640 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 30.10 _reflns_number_total 4156 _reflns_number_gt 3647 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.4000P] 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 4156 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1245 _refine_ls_wR_factor_gt 0.1194 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 N11 N 0.41877(8) 0.35331(9) 0.50942(9) 0.0183(2) Uani 1 1 d . . . N12 N 0.29927(8) 0.35277(10) 0.45545(9) 0.0190(2) Uani 1 1 d . . . C13 C 0.26499(10) 0.41188(12) 0.53241(10) 0.0203(2) Uani 1 1 d . . . H13 H 0.1852 0.4268 0.5179 0.024 Uiso 1 1 calc R . . C14 C 0.36190(11) 0.44874(12) 0.63683(11) 0.0227(2) Uani 1 1 d . . . H14 H 0.3615 0.4915 0.7051 0.027 Uiso 1 1 calc R . . C15 C 0.45860(10) 0.40909(12) 0.61859(11) 0.0216(2) Uani 1 1 d . . . H15 H 0.5389 0.4193 0.6733 0.026 Uiso 1 1 calc R . . C21 C 0.49325(9) 0.13618(11) 0.48120(10) 0.0171(2) Uani 1 1 d . . . C22 C 0.44381(10) 0.07865(12) 0.55190(10) 0.0184(2) Uani 1 1 d . . . H22 H 0.4056 0.1320 0.5880 0.022 Uiso 1 1 calc R . . C26 C 0.54981(10) 0.05647(12) 0.43030(10) 0.0181(2) Uani 1 1 d . . . H26 H 0.5846 0.0948 0.3827 0.022 Uiso 1 1 calc R . . C27 C 0.48686(10) 0.28277(12) 0.45722(11) 0.0207(2) Uani 1 1 d . . . H27A H 0.5678 0.3189 0.4902 0.025 Uiso 1 1 calc R . . H27B H 0.4509 0.2976 0.3697 0.025 Uiso 1 1 calc R . . C31 C 0.09822(9) 0.36247(10) 0.03299(10) 0.0161(2) Uani 1 1 d . . . C37 C 0.18830(9) 0.36942(11) 0.16102(10) 0.0163(2) Uani 1 1 d . . . O31 O 0.15883(8) 0.30344(9) 0.23583(8) 0.02204(19) Uani 1 1 d . . . H31 H 0.2167(14) 0.3226(16) 0.3165(15) 0.026 Uiso 1 1 d . . . O32 O 0.27763(7) 0.43411(9) 0.18922(7) 0.02073(18) Uani 1 1 d . . . C32 C 0.12653(10) 0.41638(11) -0.05551(10) 0.0173(2) Uani 1 1 d . . . H32 H 0.2020 0.4538 -0.0356 0.021 Uiso 1 1 calc R . . C33 C 0.04234(10) 0.41433(11) -0.17314(10) 0.0194(2) Uani 1 1 d . . . N33 N 0.07245(10) 0.47325(10) -0.26601(9) 0.0243(2) Uani 1 1 d . . . O33 O 0.16818(10) 0.52623(12) -0.23378(9) 0.0378(3) Uani 1 1 d . . . O34 O -0.00082(9) 0.46601(11) -0.37035(8) 0.0329(2) Uani 1 1 d . . . C34 C -0.06973(10) 0.36275(11) -0.20677(11) 0.0217(2) Uani 1 1 d . . . H34 H -0.1263 0.3621 -0.2879 0.026 Uiso 1 1 calc R . . C35 C -0.09458(10) 0.31241(11) -0.11608(11) 0.0205(2) Uani 1 1 d . . . N35 N -0.21534(9) 0.26566(10) -0.14539(11) 0.0265(2) Uani 1 1 d . . . O35 O -0.28607(8) 0.26568(10) -0.25076(10) 0.0368(3) Uani 1 1 d . . . O36 O -0.23807(9) 0.23233(10) -0.06171(10) 0.0346(2) Uani 1 1 d . . . C36 C -0.01340(10) 0.30954(11) 0.00288(11) 0.0187(2) Uani 1 1 d . . . H36 H -0.0334 0.2723 0.0625 0.022 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0153(4) 0.0182(4) 0.0202(5) 0.0010(3) 0.0062(4) 0.0007(3) N12 0.0148(4) 0.0212(5) 0.0187(4) 0.0013(4) 0.0047(4) 0.0004(3) C13 0.0173(5) 0.0207(5) 0.0212(5) 0.0021(4) 0.0064(4) 0.0023(4) C14 0.0223(5) 0.0225(5) 0.0200(5) -0.0015(4) 0.0058(4) 0.0033(4) C15 0.0183(5) 0.0206(5) 0.0205(5) -0.0008(4) 0.0029(4) 0.0008(4) C21 0.0143(5) 0.0194(5) 0.0162(5) 0.0011(4) 0.0051(4) 0.0001(4) C22 0.0171(5) 0.0218(5) 0.0179(5) -0.0002(4) 0.0091(4) 0.0017(4) C26 0.0161(5) 0.0229(5) 0.0167(5) 0.0018(4) 0.0082(4) -0.0007(4) C27 0.0207(5) 0.0201(5) 0.0243(5) 0.0026(4) 0.0125(5) 0.0012(4) C31 0.0148(5) 0.0149(5) 0.0165(5) -0.0010(4) 0.0046(4) 0.0012(4) C37 0.0154(5) 0.0167(5) 0.0164(5) -0.0005(4) 0.0063(4) 0.0021(4) O31 0.0217(4) 0.0260(4) 0.0165(4) 0.0017(3) 0.0063(3) -0.0059(3) O32 0.0168(4) 0.0257(4) 0.0192(4) -0.0009(3) 0.0073(3) -0.0037(3) C32 0.0173(5) 0.0160(5) 0.0173(5) -0.0007(4) 0.0062(4) 0.0014(4) C33 0.0222(5) 0.0175(5) 0.0171(5) -0.0002(4) 0.0071(4) 0.0038(4) N33 0.0318(5) 0.0220(5) 0.0180(5) 0.0017(4) 0.0095(4) 0.0058(4) O33 0.0432(6) 0.0452(6) 0.0249(5) 0.0033(4) 0.0144(4) -0.0141(5) O34 0.0396(6) 0.0374(5) 0.0159(4) 0.0026(4) 0.0060(4) 0.0100(4) C34 0.0200(5) 0.0187(5) 0.0196(5) -0.0034(4) 0.0018(4) 0.0043(4) C35 0.0138(5) 0.0161(5) 0.0269(6) -0.0048(4) 0.0040(4) 0.0006(4) N35 0.0149(5) 0.0179(5) 0.0397(6) -0.0055(4) 0.0047(4) 0.0005(4) O35 0.0185(4) 0.0285(5) 0.0448(6) -0.0069(4) -0.0047(4) 0.0012(4) O36 0.0213(5) 0.0310(5) 0.0520(7) -0.0027(5) 0.0161(5) -0.0048(4) C36 0.0161(5) 0.0158(5) 0.0236(5) -0.0006(4) 0.0079(4) 0.0012(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C15 1.3473(15) . ? N11 N12 1.3565(13) . ? N11 C27 1.4567(15) . ? N12 C13 1.3387(15) . ? C13 C14 1.3962(16) . ? C13 H13 0.9500 . ? C14 C15 1.3825(17) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C21 C26 1.3895(16) . ? C21 C22 1.3941(16) . ? C21 C27 1.5168(16) . ? C22 C26 1.3898(16) 3_656 ? C22 H22 0.9500 . ? C26 C22 1.3898(16) 3_656 ? C26 H26 0.9500 . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C31 C36 1.3941(15) . ? C31 C32 1.3948(16) . ? C31 C37 1.5043(15) . ? C37 O32 1.2154(14) . ? C37 O31 1.3141(14) . ? O31 H31 0.971(17) . ? C32 C33 1.3864(15) . ? C32 H32 0.9500 . ? C33 C34 1.3876(17) . ? C33 N33 1.4762(16) . ? N33 O33 1.2179(16) . ? N33 O34 1.2263(14) . ? C34 C35 1.3801(18) . ? C34 H34 0.9500 . ? C35 C36 1.3872(16) . ? C35 N35 1.4772(16) . ? N35 O35 1.2243(15) . ? N35 O36 1.2289(17) . ? C36 H36 0.9500 . ? 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 C15 N11 N12 110.92(10) . . ? C15 N11 C27 127.65(10) . . ? N12 N11 C27 120.79(10) . . ? C13 N12 N11 105.59(9) . . ? N12 C13 C14 111.11(10) . . ? N12 C13 H13 124.4 . . ? C14 C13 H13 124.4 . . ? C15 C14 C13 104.54(11) . . ? C15 C14 H14 127.7 . . ? C13 C14 H14 127.7 . . ? N11 C15 C14 107.84(10) . . ? N11 C15 H15 126.1 . . ? C14 C15 H15 126.1 . . ? C26 C21 C22 118.92(10) . . ? C26 C21 C27 118.77(10) . . ? C22 C21 C27 122.30(10) . . ? C26 C22 C21 120.22(10) 3_656 . ? C26 C22 H22 119.9 3_656 . ? C21 C22 H22 119.9 . . ? C21 C26 C22 120.85(10) . 3_656 ? C21 C26 H26 119.6 . . ? C22 C26 H26 119.6 3_656 . ? N11 C27 C21 113.03(9) . . ? N11 C27 H27A 109.0 . . ? C21 C27 H27A 109.0 . . ? N11 C27 H27B 109.0 . . ? C21 C27 H27B 109.0 . . ? H27A C27 H27B 107.8 . . ? C36 C31 C32 120.14(10) . . ? C36 C31 C37 121.33(10) . . ? C32 C31 C37 118.46(10) . . ? O32 C37 O31 125.04(10) . . ? O32 C37 C31 121.11(10) . . ? O31 C37 C31 113.83(10) . . ? C37 O31 H31 107.9(10) . . ? C33 C32 C31 118.69(10) . . ? C33 C32 H32 120.7 . . ? C31 C32 H32 120.7 . . ? C32 C33 C34 122.93(11) . . ? C32 C33 N33 118.34(11) . . ? C34 C33 N33 118.70(10) . . ? O33 N33 O34 124.43(11) . . ? O33 N33 C33 117.79(10) . . ? O34 N33 C33 117.78(11) . . ? C35 C34 C33 116.42(10) . . ? C35 C34 H34 121.8 . . ? C33 C34 H34 121.8 . . ? C34 C35 C36 123.30(11) . . ? C34 C35 N35 118.69(11) . . ? C36 C35 N35 117.93(11) . . ? O35 N35 O36 124.79(12) . . ? O35 N35 C35 117.76(12) . . ? O36 N35 C35 117.43(11) . . ? C35 C36 C31 118.50(11) . . ? C35 C36 H36 120.7 . . ? C31 C36 H36 120.7 . . ? 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 C15 N11 N12 C13 1.17(13) . . . . ? C27 N11 N12 C13 172.71(10) . . . . ? N11 N12 C13 C14 -0.97(13) . . . . ? N12 C13 C14 C15 0.43(14) . . . . ? N12 N11 C15 C14 -0.92(14) . . . . ? C27 N11 C15 C14 -171.74(11) . . . . ? C13 C14 C15 N11 0.30(14) . . . . ? C26 C21 C22 C26 -0.71(18) . . . 3_656 ? C27 C21 C22 C26 178.92(11) . . . 3_656 ? C22 C21 C26 C22 0.71(18) . . . 3_656 ? C27 C21 C26 C22 -178.93(10) . . . 3_656 ? C15 N11 C27 C21 91.12(14) . . . . ? N12 N11 C27 C21 -78.89(13) . . . . ? C26 C21 C27 N11 176.26(10) . . . . ? C22 C21 C27 N11 -3.37(16) . . . . ? C36 C31 C37 O32 -167.87(11) . . . . ? C32 C31 C37 O32 8.97(16) . . . . ? C36 C31 C37 O31 10.36(15) . . . . ? C32 C31 C37 O31 -172.80(10) . . . . ? C36 C31 C32 C33 -0.90(16) . . . . ? C37 C31 C32 C33 -177.78(10) . . . . ? C31 C32 C33 C34 1.01(17) . . . . ? C31 C32 C33 N33 179.16(10) . . . . ? C32 C33 N33 O33 -3.28(16) . . . . ? C34 C33 N33 O33 174.95(11) . . . . ? C32 C33 N33 O34 177.01(11) . . . . ? C34 C33 N33 O34 -4.76(16) . . . . ? C32 C33 C34 C35 0.03(17) . . . . ? N33 C33 C34 C35 -178.11(10) . . . . ? C33 C34 C35 C36 -1.24(17) . . . . ? C33 C34 C35 N35 175.33(10) . . . . ? C34 C35 N35 O35 4.79(16) . . . . ? C36 C35 N35 O35 -178.46(11) . . . . ? C34 C35 N35 O36 -173.62(11) . . . . ? C36 C35 N35 O36 3.13(16) . . . . ? C34 C35 C36 C31 1.34(17) . . . . ? N35 C35 C36 C31 -175.25(10) . . . . ? C32 C31 C36 C35 -0.21(16) . . . . ? C37 C31 C36 C35 176.58(10) . . . . ? 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 O31 H31 N12 0.971(17) 1.612(17) 2.5786(14) 172.7(15) . _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 30.10 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.509 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.059 #END data_2a _database_code_depnum_ccdc_archive 'CCDC 607723' _audit_creation_method SHELXL-97 _chemical_name_systematic ; MF142Me8 1,4-bis[(3,5-dimethylpyrazol-1-yl)methyl]benzene, (2,6-Cl2PhCOOH)2 ; _chemical_name_common ;MF142Me8 1,4-bis((3,5-dimethylpyrazol-1-yl)methyl)benzene, (2,6-Cl2PhCOOH)2 ; _chemical_melting_point ? _chemical_formula_moiety ; (C18 H22 N4) (C7 H4 Cl2 O2)2 ; _chemical_formula_sum 'C32 H30 Cl4 N4 O4' _chemical_formula_weight 676.40 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5783(8) _cell_length_b 7.9010(9) _cell_length_c 14.1442(13) _cell_angle_alpha 103.784(7) _cell_angle_beta 101.429(7) _cell_angle_gamma 90.509(6) _cell_volume 804.80(15) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1494 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 27.50 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 350 _exptl_absorpt_coefficient_mu 0.411 _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 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6024 _diffrn_reflns_av_R_equivalents 0.0913 _diffrn_reflns_av_sigmaI/netI 0.0773 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 27.89 _reflns_number_total 3580 _reflns_number_gt 2707 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] 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 3580 _refine_ls_number_parameters 204 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0804 _refine_ls_R_factor_gt 0.0666 _refine_ls_wR_factor_ref 0.2060 _refine_ls_wR_factor_gt 0.1956 _refine_ls_goodness_of_fit_ref 1.357 _refine_ls_restrained_S_all 1.357 _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 C11 C 0.1625(3) 0.4168(3) 0.49846(17) 0.0253(5) Uani 1 1 d . . . C12 C 0.0366(4) 0.4067(3) 0.41102(17) 0.0287(5) Uani 1 1 d . . . H12 H 0.0608 0.3428 0.3495 0.043 Uiso 1 1 calc R . . C16 C 0.1236(4) 0.5114(3) 0.58733(17) 0.0283(5) Uani 1 1 d . . . H16 H 0.2082 0.5199 0.6478 0.043 Uiso 1 1 calc R . . C17 C 0.3349(3) 0.3234(3) 0.49559(18) 0.0283(5) Uani 1 1 d . . . H17A H 0.3953 0.3569 0.4462 0.034 Uiso 1 1 calc R . . H17B H 0.4171 0.3597 0.5616 0.034 Uiso 1 1 calc R . . N21 N 0.2996(3) 0.1348(3) 0.46937(14) 0.0258(5) Uani 1 1 d . . . N22 N 0.2662(3) 0.0469(3) 0.37229(14) 0.0281(5) Uani 1 1 d . . . C23 C 0.2166(4) -0.1179(3) 0.37017(19) 0.0300(5) Uani 1 1 d . . . C24 C 0.2175(4) -0.1319(3) 0.4664(2) 0.0333(6) Uani 1 1 d . . . H24 H 0.1883 -0.2342 0.4858 0.040 Uiso 1 1 calc R . . C25 C 0.2687(3) 0.0308(3) 0.52807(18) 0.0295(6) Uani 1 1 d . . . C26 C 0.1729(4) -0.2527(4) 0.2751(2) 0.0418(7) Uani 1 1 d . . . H26A H 0.1628 -0.1968 0.2196 0.063 Uiso 1 1 calc R . . H26B H 0.0583 -0.3155 0.2705 0.063 Uiso 1 1 calc R . . H26C H 0.2688 -0.3350 0.2723 0.063 Uiso 1 1 calc R . . C27 C 0.2885(4) 0.0954(4) 0.63760(19) 0.0411(7) Uani 1 1 d . . . H27A H 0.1834 0.1602 0.6520 0.062 Uiso 1 1 calc R . . H27B H 0.3980 0.1724 0.6647 0.062 Uiso 1 1 calc R . . H27C H 0.2971 -0.0040 0.6683 0.062 Uiso 1 1 calc R . . C31 C 0.4503(4) 0.2579(3) 0.10983(17) 0.0316(6) Uani 1 1 d . . . C37 C 0.4158(4) 0.2576(3) 0.21106(18) 0.0299(5) Uani 1 1 d . . . O31 O 0.3402(3) 0.1092(3) 0.21169(14) 0.0420(5) Uani 1 1 d . . . H31 H 0.316(5) 0.107(5) 0.270(3) 0.050 Uiso 1 1 d . . . O32 O 0.4543(3) 0.3832(3) 0.28059(13) 0.0404(5) Uani 1 1 d . . . C32 C 0.6127(4) 0.2124(4) 0.08341(19) 0.0358(6) Uani 1 1 d . . . Cl1 Cl 0.78228(11) 0.15339(11) 0.16915(6) 0.0484(3) Uani 1 1 d . . . C33 C 0.6430(5) 0.2091(5) -0.0106(2) 0.0489(8) Uani 1 1 d . . . H33 H 0.7543 0.1745 -0.0281 0.059 Uiso 1 1 calc R . . C34 C 0.5072(5) 0.2573(5) -0.0780(2) 0.0562(10) Uani 1 1 d . . . H34 H 0.5268 0.2574 -0.1423 0.067 Uiso 1 1 calc R . . C35 C 0.3455(5) 0.3047(5) -0.0547(2) 0.0529(9) Uani 1 1 d . . . H35 H 0.2537 0.3384 -0.1018 0.063 Uiso 1 1 calc R . . C36 C 0.3176(4) 0.3027(4) 0.0391(2) 0.0398(7) Uani 1 1 d . . . Cl2 Cl 0.11247(12) 0.35957(12) 0.06961(6) 0.0579(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 C11 0.0283(12) 0.0193(11) 0.0292(11) 0.0065(9) 0.0073(9) -0.0007(9) C12 0.0378(14) 0.0247(12) 0.0226(11) 0.0039(9) 0.0066(10) 0.0007(10) C16 0.0328(13) 0.0260(12) 0.0252(11) 0.0059(9) 0.0040(9) 0.0001(10) C17 0.0316(13) 0.0215(12) 0.0317(12) 0.0061(9) 0.0072(10) 0.0021(10) N21 0.0274(10) 0.0250(10) 0.0277(10) 0.0077(8) 0.0105(8) 0.0036(8) N22 0.0330(11) 0.0261(11) 0.0269(10) 0.0052(8) 0.0120(8) 0.0013(9) C23 0.0303(13) 0.0224(12) 0.0385(13) 0.0063(10) 0.0116(10) 0.0005(10) C24 0.0387(14) 0.0243(12) 0.0455(14) 0.0173(11) 0.0178(12) 0.0056(11) C25 0.0286(12) 0.0336(13) 0.0324(12) 0.0155(11) 0.0110(10) 0.0096(10) C26 0.0510(18) 0.0288(14) 0.0436(15) -0.0004(12) 0.0167(13) -0.0026(13) C27 0.0475(17) 0.0501(17) 0.0309(13) 0.0174(12) 0.0113(12) 0.0103(14) C31 0.0395(15) 0.0276(13) 0.0272(12) 0.0049(10) 0.0083(11) -0.0054(11) C37 0.0309(13) 0.0314(13) 0.0290(12) 0.0090(10) 0.0081(10) 0.0011(10) O31 0.0639(14) 0.0357(11) 0.0307(10) 0.0071(8) 0.0209(10) -0.0042(10) O32 0.0512(12) 0.0392(11) 0.0300(9) 0.0030(8) 0.0134(9) -0.0058(9) C32 0.0402(15) 0.0366(15) 0.0286(12) 0.0026(11) 0.0091(11) -0.0100(12) Cl1 0.0424(5) 0.0586(5) 0.0452(4) 0.0109(3) 0.0135(3) 0.0045(4) C33 0.056(2) 0.057(2) 0.0312(14) -0.0024(13) 0.0191(14) -0.0164(16) C34 0.071(2) 0.066(2) 0.0295(14) 0.0063(14) 0.0132(15) -0.0268(19) C35 0.069(2) 0.057(2) 0.0281(14) 0.0133(13) -0.0025(14) -0.0167(17) C36 0.0469(17) 0.0392(16) 0.0310(13) 0.0085(11) 0.0028(12) -0.0074(13) Cl2 0.0477(5) 0.0703(6) 0.0551(5) 0.0197(4) 0.0035(4) 0.0098(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C11 C16 1.389(3) . ? C11 C12 1.389(3) . ? C11 C17 1.509(3) . ? C12 C16 1.382(4) 2_566 ? C12 H12 0.9500 . ? C16 C12 1.382(4) 2_566 ? C16 H16 0.9500 . ? C17 N21 1.456(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? N21 C25 1.348(3) . ? N21 N22 1.355(3) . ? N22 C23 1.344(3) . ? C23 C24 1.391(3) . ? C23 C26 1.478(4) . ? C24 C25 1.374(4) . ? C24 H24 0.9500 . ? C25 C27 1.488(4) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C31 C32 1.382(4) . ? C31 C36 1.384(4) . ? C31 C37 1.506(3) . ? C37 O32 1.206(3) . ? C37 O31 1.303(3) . ? O31 H31 0.88(3) . ? C32 C33 1.388(4) . ? C32 Cl1 1.733(3) . ? C33 C34 1.379(5) . ? C33 H33 0.9500 . ? C34 C35 1.364(6) . ? C34 H34 0.9500 . ? C35 C36 1.387(4) . ? C35 H35 0.9500 . ? C36 Cl2 1.729(3) . ? 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 C16 C11 C12 118.4(2) . . ? C16 C11 C17 121.6(2) . . ? C12 C11 C17 120.0(2) . . ? C16 C12 C11 120.7(2) 2_566 . ? C16 C12 H12 119.7 2_566 . ? C11 C12 H12 119.7 . . ? C12 C16 C11 120.9(2) 2_566 . ? C12 C16 H16 119.5 2_566 . ? C11 C16 H16 119.5 . . ? N21 C17 C11 111.2(2) . . ? N21 C17 H17A 109.4 . . ? C11 C17 H17A 109.4 . . ? N21 C17 H17B 109.4 . . ? C11 C17 H17B 109.4 . . ? H17A C17 H17B 108.0 . . ? C25 N21 N22 111.4(2) . . ? C25 N21 C17 128.5(2) . . ? N22 N21 C17 119.34(18) . . ? C23 N22 N21 105.97(19) . . ? N22 C23 C24 109.5(2) . . ? N22 C23 C26 120.8(2) . . ? C24 C23 C26 129.7(2) . . ? C25 C24 C23 106.7(2) . . ? C25 C24 H24 126.7 . . ? C23 C24 H24 126.7 . . ? N21 C25 C24 106.5(2) . . ? N21 C25 C27 122.7(2) . . ? C24 C25 C27 130.8(2) . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C32 C31 C36 117.5(2) . . ? C32 C31 C37 122.0(2) . . ? C36 C31 C37 120.5(3) . . ? O32 C37 O31 126.3(2) . . ? O32 C37 C31 122.0(2) . . ? O31 C37 C31 111.7(2) . . ? C37 O31 H31 114(2) . . ? C31 C32 C33 122.0(3) . . ? C31 C32 Cl1 119.18(19) . . ? C33 C32 Cl1 118.9(3) . . ? C34 C33 C32 118.3(3) . . ? C34 C33 H33 120.9 . . ? C32 C33 H33 120.9 . . ? C35 C34 C33 121.7(3) . . ? C35 C34 H34 119.2 . . ? C33 C34 H34 119.2 . . ? C34 C35 C36 118.8(3) . . ? C34 C35 H35 120.6 . . ? C36 C35 H35 120.6 . . ? C31 C36 C35 121.8(3) . . ? C31 C36 Cl2 118.7(2) . . ? C35 C36 Cl2 119.5(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 C16 C11 C12 C16 -0.1(4) . . . 2_566 ? C17 C11 C12 C16 178.7(2) . . . 2_566 ? C12 C11 C16 C12 0.1(4) . . . 2_566 ? C17 C11 C16 C12 -178.7(2) . . . 2_566 ? C16 C11 C17 N21 110.5(3) . . . . ? C12 C11 C17 N21 -68.3(3) . . . . ? C11 C17 N21 C25 -79.8(3) . . . . ? C11 C17 N21 N22 89.6(3) . . . . ? C25 N21 N22 C23 -1.3(3) . . . . ? C17 N21 N22 C23 -172.4(2) . . . . ? N21 N22 C23 C24 0.6(3) . . . . ? N21 N22 C23 C26 -178.8(2) . . . . ? N22 C23 C24 C25 0.3(3) . . . . ? C26 C23 C24 C25 179.6(3) . . . . ? N22 N21 C25 C24 1.5(3) . . . . ? C17 N21 C25 C24 171.5(2) . . . . ? N22 N21 C25 C27 -177.8(2) . . . . ? C17 N21 C25 C27 -7.7(4) . . . . ? C23 C24 C25 N21 -1.0(3) . . . . ? C23 C24 C25 C27 178.2(3) . . . . ? C32 C31 C37 O32 87.8(3) . . . . ? C36 C31 C37 O32 -92.9(3) . . . . ? C32 C31 C37 O31 -92.9(3) . . . . ? C36 C31 C37 O31 86.4(3) . . . . ? C36 C31 C32 C33 -0.7(4) . . . . ? C37 C31 C32 C33 178.6(3) . . . . ? C36 C31 C32 Cl1 -179.4(2) . . . . ? C37 C31 C32 Cl1 -0.1(4) . . . . ? C31 C32 C33 C34 1.7(5) . . . . ? Cl1 C32 C33 C34 -179.7(2) . . . . ? C32 C33 C34 C35 -1.0(5) . . . . ? C33 C34 C35 C36 -0.5(5) . . . . ? C32 C31 C36 C35 -0.9(4) . . . . ? C37 C31 C36 C35 179.8(3) . . . . ? C32 C31 C36 Cl2 179.8(2) . . . . ? C37 C31 C36 Cl2 0.5(4) . . . . ? C34 C35 C36 C31 1.5(5) . . . . ? C34 C35 C36 Cl2 -179.2(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 O31 H31 N22 0.88(3) 1.73(3) 2.598(3) 166(4) . _diffrn_measured_fraction_theta_max 0.932 _diffrn_reflns_theta_full 27.89 _diffrn_measured_fraction_theta_full 0.932 _refine_diff_density_max 0.500 _refine_diff_density_min -0.339 _refine_diff_density_rms 0.097 #END data_2b _database_code_depnum_ccdc_archive 'CCDC 607724' _audit_creation_method SHELXL-97 _chemical_name_systematic ; MF142Me8 1,4-bis[(3,5-dimethylpyrazol-1-yl)methyl]benzene (Me5-PhCOOH)2 ; _chemical_name_common ;MF142Me8 1,4-bis((3,5-dimethylpyrazol-1-yl)methyl)benzene (Me5-PhCOOH)2 ; _chemical_melting_point ? _chemical_formula_moiety ; (C18 H22 N4) (C12 H16 O2)2 ; _chemical_formula_sum 'C42 H54 N4 O4' _chemical_formula_weight 678.89 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8093(6) _cell_length_b 14.7493(10) _cell_length_c 15.4238(12) _cell_angle_alpha 67.222(4) _cell_angle_beta 82.777(4) _cell_angle_gamma 86.232(4) _cell_volume 1832.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3705 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 27.30 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.230 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 732 _exptl_absorpt_coefficient_mu 0.079 _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 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13688 _diffrn_reflns_av_R_equivalents 0.1094 _diffrn_reflns_av_sigmaI/netI 0.1160 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 27.49 _reflns_number_total 8055 _reflns_number_gt 4721 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] 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 8055 _refine_ls_number_parameters 471 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1184 _refine_ls_R_factor_gt 0.0798 _refine_ls_wR_factor_ref 0.2413 _refine_ls_wR_factor_gt 0.2154 _refine_ls_goodness_of_fit_ref 1.231 _refine_ls_restrained_S_all 1.231 _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 N11 N 0.5590(3) 0.76338(17) 0.46401(15) 0.0265(5) Uani 1 1 d . . . N12 N 0.5117(3) 0.69707(17) 0.55115(15) 0.0274(5) Uani 1 1 d . . . C13 C 0.4254(3) 0.6340(2) 0.53782(19) 0.0285(6) Uani 1 1 d . . . C14 C 0.4169(3) 0.6608(2) 0.44095(19) 0.0306(7) Uani 1 1 d . . . H14A H 0.3624 0.6281 0.4124 0.037 Uiso 1 1 calc R . . C15 C 0.5025(3) 0.7433(2) 0.39560(19) 0.0295(6) Uani 1 1 d . . . C16 C 0.3515(4) 0.5520(2) 0.6198(2) 0.0390(8) Uani 1 1 d . . . H16A H 0.3859 0.5508 0.6782 0.059 Uiso 1 1 calc R . . H16B H 0.3796 0.4896 0.6128 0.059 Uiso 1 1 calc R . . H16C H 0.2401 0.5615 0.6225 0.059 Uiso 1 1 calc R . . C17 C 0.5354(4) 0.8033(3) 0.2930(2) 0.0417(8) Uani 1 1 d . . . H17A H 0.5055 0.8720 0.2807 0.063 Uiso 1 1 calc R . . H17B H 0.4773 0.7783 0.2570 0.063 Uiso 1 1 calc R . . H17C H 0.6451 0.7991 0.2737 0.063 Uiso 1 1 calc R . . C21 C 0.5743(3) 0.9229(2) 0.47884(18) 0.0259(6) Uani 1 1 d . . . C22 C 0.4656(3) 0.9820(2) 0.42370(19) 0.0336(7) Uani 1 1 d . . . H22A H 0.4408 0.9702 0.3709 0.040 Uiso 1 1 calc R . . C26 C 0.6071(3) 0.9419(2) 0.5553(2) 0.0343(7) Uani 1 1 d . . . H26A H 0.6809 0.9019 0.5941 0.041 Uiso 1 1 calc R . . C27 C 0.6588(3) 0.8421(2) 0.4550(2) 0.0306(6) Uani 1 1 d . . . H27A H 0.7090 0.8702 0.3893 0.037 Uiso 1 1 calc R . . H27B H 0.7399 0.8144 0.4976 0.037 Uiso 1 1 calc R . . N31 N 0.9527(2) 0.26768(16) 0.44491(14) 0.0245(5) Uani 1 1 d . . . N32 N 0.9823(3) 0.30276(17) 0.51105(15) 0.0273(5) Uani 1 1 d . . . C33 C 1.0899(3) 0.3698(2) 0.46723(19) 0.0291(6) Uani 1 1 d . . . C34 C 1.1274(3) 0.3782(2) 0.3745(2) 0.0311(7) Uani 1 1 d . . . H34A H 1.1995 0.4215 0.3286 0.037 Uiso 1 1 calc R . . C35 C 1.0399(3) 0.3117(2) 0.36187(18) 0.0279(6) Uani 1 1 d . . . C36 C 1.1565(4) 0.4207(2) 0.5194(2) 0.0413(8) Uani 1 1 d . . . H36A H 1.0868 0.4159 0.5757 0.062 Uiso 1 1 calc R . . H36B H 1.1715 0.4901 0.4784 0.062 Uiso 1 1 calc R . . H36C H 1.2552 0.3897 0.5387 0.062 Uiso 1 1 calc R . . C37 C 1.0353(4) 0.2856(2) 0.2789(2) 0.0393(8) Uani 1 1 d . . . H37A H 0.9286 0.2839 0.2677 0.059 Uiso 1 1 calc R . . H37B H 1.0839 0.2209 0.2908 0.059 Uiso 1 1 calc R . . H37C H 1.0902 0.3349 0.2231 0.059 Uiso 1 1 calc R . . C41 C 0.9253(3) 0.08993(19) 0.48642(18) 0.0245(6) Uani 1 1 d . . . C42 C 0.9248(3) 0.0472(2) 0.42100(18) 0.0275(6) Uani 1 1 d . . . H42A H 0.8730 0.0793 0.3663 0.033 Uiso 1 1 calc R . . C46 C 1.0009(3) 0.0420(2) 0.56555(18) 0.0269(6) Uani 1 1 d . . . H46A H 1.0019 0.0706 0.6111 0.032 Uiso 1 1 calc R . . C47 C 0.8458(3) 0.18816(19) 0.47039(18) 0.0259(6) Uani 1 1 d . . . H47A H 0.7790 0.2033 0.4193 0.031 Uiso 1 1 calc R . . H47B H 0.7799 0.1838 0.5287 0.031 Uiso 1 1 calc R . . C51 C 0.4298(3) 0.6914(2) 0.86775(18) 0.0279(6) Uani 1 1 d . A . C52 C 0.4972(3) 0.7530(2) 0.90092(18) 0.0283(6) Uani 1 1 d . . . C53 C 0.4842(3) 0.7298(2) 0.99821(19) 0.0310(7) Uani 1 1 d . A . C54 C 0.4065(3) 0.6463(2) 1.06102(19) 0.0305(7) Uani 1 1 d . . . C55 C 0.3395(3) 0.5852(2) 1.02684(19) 0.0308(7) Uani 1 1 d . A . C56 C 0.3504(3) 0.6083(2) 0.92906(19) 0.0284(6) Uani 1 1 d . . . C61 C 0.4318(3) 0.7194(2) 0.76358(18) 0.0287(6) Uani 1 1 d . . . O61 O 0.5504(2) 0.68240(16) 0.72536(14) 0.0352(5) Uani 1 1 d . A . H61 H 0.539(4) 0.699(2) 0.663(2) 0.042 Uiso 1 1 d . . . O62 O 0.3344(2) 0.76863(18) 0.71853(14) 0.0482(6) Uani 1 1 d . A . C62 C 0.5799(4) 0.8423(2) 0.8319(2) 0.0376(7) Uani 1 1 d . . . H62A H 0.5788 0.8449 0.7675 0.056 Uiso 1 1 calc R . . H62B H 0.6861 0.8389 0.8460 0.056 Uiso 1 1 calc R . . H62C H 0.5291 0.9014 0.8370 0.056 Uiso 1 1 calc R . . C63 C 0.5503(4) 0.7972(2) 1.0356(2) 0.0395(8) Uani 1 1 d . . . H63A H 0.4690 0.8201 1.0723 0.059 Uiso 1 1 calc R A . H63B H 0.5958 0.8539 0.9826 0.059 Uiso 1 1 calc R . . H63C H 0.6292 0.7616 1.0764 0.059 Uiso 1 1 calc R . . C64A C 0.3922(4) 0.6217(3) 1.1662(2) 0.0441(8) Uani 0.68(4) 1 d P A 1 H64A H 0.3821 0.5505 1.2001 0.066 Uiso 0.68(4) 1 calc PR A 1 H64B H 0.3015 0.6553 1.1843 0.066 Uiso 0.68(4) 1 calc PR A 1 H64C H 0.4836 0.6434 1.1824 0.066 Uiso 0.68(4) 1 calc PR A 1 C64B C 0.3922(4) 0.6217(3) 1.1662(2) 0.0441(8) Uani 0.32(4) 1 d P A 2 H64D H 0.3011 0.5820 1.1965 0.066 Uiso 0.32(4) 1 calc PR A 2 H64E H 0.3828 0.6826 1.1780 0.066 Uiso 0.32(4) 1 calc PR A 2 H64F H 0.4833 0.5845 1.1923 0.066 Uiso 0.32(4) 1 calc PR A 2 C65 C 0.2535(4) 0.4955(2) 1.0933(2) 0.0435(8) Uani 1 1 d . . . H65A H 0.2222 0.4590 1.0575 0.065 Uiso 1 1 calc R A . H65B H 0.1626 0.5156 1.1256 0.065 Uiso 1 1 calc R . . H65C H 0.3197 0.4534 1.1403 0.065 Uiso 1 1 calc R . . C66 C 0.2788(4) 0.5431(2) 0.8912(2) 0.0389(7) Uani 1 1 d . A . H66A H 0.2968 0.5703 0.8220 0.058 Uiso 1 1 calc R . . H66B H 0.1685 0.5397 0.9109 0.058 Uiso 1 1 calc R . . H66C H 0.3247 0.4770 0.9161 0.058 Uiso 1 1 calc R . . C71 C 0.9403(3) 0.1876(2) 0.85024(18) 0.0267(6) Uani 1 1 d . . . C72 C 0.8559(3) 0.1062(2) 0.91035(19) 0.0292(6) Uani 1 1 d . B . C73 C 0.8370(3) 0.0853(2) 1.00802(19) 0.0294(6) Uani 1 1 d . . . C74 C 0.9030(3) 0.1463(2) 1.04244(19) 0.0315(7) Uani 1 1 d . B . C75 C 0.9808(3) 0.2306(2) 0.9803(2) 0.0319(7) Uani 1 1 d . . . C76 C 1.0022(3) 0.2509(2) 0.88306(19) 0.0303(7) Uani 1 1 d . B . C81 C 0.9749(3) 0.2021(2) 0.74800(19) 0.0299(6) Uani 1 1 d . . . O81 O 0.8782(2) 0.26016(16) 0.69220(14) 0.0383(6) Uani 1 1 d . . . H81 H 0.914(4) 0.267(2) 0.629(2) 0.046 Uiso 1 1 d . . . O82 O 1.0827(3) 0.16330(19) 0.72035(14) 0.0508(7) Uani 1 1 d . . . C82 C 0.7865(4) 0.0404(2) 0.8731(2) 0.0361(7) Uani 1 1 d . . . H82A H 0.8145 0.0630 0.8047 0.054 Uiso 1 1 calc R B . H82B H 0.6749 0.0423 0.8865 0.054 Uiso 1 1 calc R . . H82C H 0.8247 -0.0271 0.9039 0.054 Uiso 1 1 calc R . . C83A C 0.7469(4) -0.0032(2) 1.0731(2) 0.0434(8) Uani 0.65(4) 1 d P B 1 H83A H 0.8095 -0.0629 1.0820 0.065 Uiso 0.65(4) 1 calc PR B 1 H83B H 0.6543 -0.0065 1.0454 0.065 Uiso 0.65(4) 1 calc PR B 1 H83C H 0.7182 0.0022 1.1345 0.065 Uiso 0.65(4) 1 calc PR B 1 C83B C 0.7469(4) -0.0032(2) 1.0731(2) 0.0434(8) Uani 0.35(4) 1 d P B 2 H83D H 0.7991 -0.0374 1.1299 0.065 Uiso 0.35(4) 1 calc PR B 2 H83E H 0.7386 -0.0478 1.0406 0.065 Uiso 0.35(4) 1 calc PR B 2 H83F H 0.6443 0.0179 1.0914 0.065 Uiso 0.35(4) 1 calc PR B 2 C84 C 0.8896(4) 0.1216(3) 1.1475(2) 0.0445(8) Uani 1 1 d . . . H84A H 0.8783 0.0504 1.1815 0.067 Uiso 1 1 calc R B . H84B H 0.7998 0.1558 1.1658 0.067 Uiso 1 1 calc R . . H84C H 0.9819 0.1425 1.1636 0.067 Uiso 1 1 calc R . . C85 C 1.0430(4) 0.2992(3) 1.0180(2) 0.0420(8) Uani 1 1 d . B . H85A H 0.9676 0.3082 1.0666 0.063 Uiso 1 1 calc R . . H85B H 1.0639 0.3630 0.9662 0.063 Uiso 1 1 calc R . . H85C H 1.1380 0.2711 1.0456 0.063 Uiso 1 1 calc R . . C86 C 1.0889(4) 0.3389(2) 0.8147(2) 0.0412(8) Uani 1 1 d . . . H86A H 1.1135 0.3321 0.7537 0.062 Uiso 1 1 calc R B . H86B H 1.1838 0.3437 0.8396 0.062 Uiso 1 1 calc R . . H86C H 1.0260 0.3985 0.8061 0.062 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0288(12) 0.0265(12) 0.0260(12) -0.0125(10) -0.0011(9) -0.0004(10) N12 0.0307(12) 0.0253(13) 0.0270(12) -0.0109(10) -0.0034(10) -0.0004(10) C13 0.0288(14) 0.0279(15) 0.0317(15) -0.0146(12) -0.0040(11) 0.0020(12) C14 0.0283(15) 0.0352(17) 0.0343(15) -0.0195(13) -0.0061(12) 0.0011(13) C15 0.0274(14) 0.0373(17) 0.0274(14) -0.0167(13) -0.0042(11) 0.0049(13) C16 0.0469(19) 0.0340(17) 0.0375(17) -0.0138(14) -0.0044(14) -0.0097(14) C17 0.0461(19) 0.050(2) 0.0303(16) -0.0169(15) -0.0046(14) -0.0007(16) C21 0.0236(13) 0.0247(14) 0.0273(14) -0.0087(11) 0.0038(11) -0.0061(11) C22 0.0391(17) 0.0372(17) 0.0269(14) -0.0144(13) -0.0049(12) -0.0024(14) C26 0.0345(16) 0.0366(17) 0.0327(15) -0.0131(13) -0.0085(12) 0.0010(13) C27 0.0315(15) 0.0292(16) 0.0316(15) -0.0130(12) 0.0011(12) -0.0041(12) N31 0.0290(12) 0.0264(12) 0.0220(11) -0.0136(9) -0.0026(9) 0.0000(10) N32 0.0311(12) 0.0300(13) 0.0252(12) -0.0145(10) -0.0067(10) 0.0020(10) C33 0.0264(14) 0.0282(15) 0.0352(15) -0.0144(13) -0.0078(12) 0.0040(12) C34 0.0305(15) 0.0256(15) 0.0335(15) -0.0072(12) -0.0006(12) -0.0052(12) C35 0.0297(14) 0.0274(15) 0.0246(14) -0.0080(12) -0.0016(11) -0.0017(12) C36 0.0370(17) 0.0409(19) 0.056(2) -0.0269(16) -0.0126(15) 0.0024(15) C37 0.0476(19) 0.048(2) 0.0249(14) -0.0165(14) 0.0008(13) -0.0141(15) C41 0.0231(13) 0.0247(14) 0.0253(13) -0.0093(11) -0.0006(10) -0.0042(11) C42 0.0317(15) 0.0270(15) 0.0240(13) -0.0084(11) -0.0065(11) -0.0033(12) C46 0.0318(15) 0.0287(15) 0.0254(13) -0.0161(12) -0.0013(11) -0.0045(12) C47 0.0251(13) 0.0282(15) 0.0234(13) -0.0091(11) 0.0003(10) -0.0031(11) C51 0.0283(14) 0.0311(16) 0.0240(13) -0.0108(12) -0.0034(11) 0.0041(12) C52 0.0309(15) 0.0309(15) 0.0238(13) -0.0111(12) -0.0041(11) 0.0016(12) C53 0.0296(15) 0.0375(17) 0.0298(15) -0.0168(13) -0.0080(12) 0.0067(13) C54 0.0305(15) 0.0381(17) 0.0248(14) -0.0142(13) -0.0052(11) 0.0051(13) C55 0.0301(15) 0.0313(16) 0.0277(14) -0.0084(12) -0.0018(11) 0.0018(12) C56 0.0270(14) 0.0294(15) 0.0287(14) -0.0112(12) -0.0031(11) 0.0008(12) C61 0.0293(15) 0.0344(16) 0.0252(14) -0.0137(12) -0.0036(11) -0.0050(13) O61 0.0387(12) 0.0442(13) 0.0234(10) -0.0145(9) -0.0041(9) 0.0049(10) O62 0.0443(13) 0.0701(17) 0.0322(11) -0.0217(11) -0.0142(10) 0.0182(12) C62 0.0456(18) 0.0387(18) 0.0276(15) -0.0113(13) -0.0020(13) -0.0089(15) C63 0.0470(19) 0.0436(19) 0.0349(16) -0.0214(15) -0.0098(14) 0.0021(15) C64A 0.051(2) 0.054(2) 0.0257(15) -0.0142(15) -0.0045(14) 0.0023(17) C64B 0.051(2) 0.054(2) 0.0257(15) -0.0142(15) -0.0045(14) 0.0023(17) C65 0.0437(19) 0.0400(19) 0.0398(17) -0.0074(15) -0.0044(14) -0.0028(15) C66 0.0417(18) 0.0396(18) 0.0401(17) -0.0202(15) -0.0023(14) -0.0068(14) C71 0.0280(14) 0.0322(16) 0.0241(13) -0.0150(12) -0.0051(11) 0.0029(12) C72 0.0261(14) 0.0330(16) 0.0289(14) -0.0120(12) -0.0066(11) 0.0037(12) C73 0.0295(15) 0.0335(16) 0.0265(14) -0.0139(12) -0.0014(11) 0.0028(12) C74 0.0308(15) 0.0400(17) 0.0268(14) -0.0169(13) -0.0044(12) 0.0060(13) C75 0.0311(15) 0.0361(17) 0.0359(16) -0.0211(13) -0.0101(12) 0.0070(13) C76 0.0310(15) 0.0304(16) 0.0301(15) -0.0117(12) -0.0062(12) 0.0025(12) C81 0.0305(15) 0.0361(17) 0.0274(14) -0.0170(13) -0.0008(12) -0.0025(13) O81 0.0387(12) 0.0514(14) 0.0257(10) -0.0164(10) -0.0070(9) 0.0101(10) O82 0.0454(13) 0.0726(17) 0.0309(12) -0.0199(12) -0.0027(10) 0.0195(13) C82 0.0391(17) 0.0379(17) 0.0349(16) -0.0177(14) -0.0036(13) -0.0031(14) C83A 0.0419(18) 0.048(2) 0.0328(16) -0.0080(15) -0.0006(14) -0.0028(16) C83B 0.0419(18) 0.048(2) 0.0328(16) -0.0080(15) -0.0006(14) -0.0028(16) C84 0.050(2) 0.057(2) 0.0280(16) -0.0191(15) -0.0041(14) 0.0063(17) C85 0.0469(19) 0.046(2) 0.0439(18) -0.0282(16) -0.0122(15) 0.0035(16) C86 0.0460(19) 0.0344(18) 0.0447(18) -0.0151(15) -0.0076(15) -0.0060(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 N12 1.353(3) . ? N11 C15 1.357(3) . ? N11 C27 1.456(4) . ? N12 C13 1.329(4) . ? C13 C14 1.400(4) . ? C13 C16 1.482(4) . ? C14 C15 1.367(4) . ? C14 H14A 0.9500 . ? C15 C17 1.485(4) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C21 C26 1.379(4) . ? C21 C22 1.386(3) . ? C21 C27 1.505(4) . ? C22 C26 1.382(4) 2_676 ? C22 H22A 0.9500 . ? C26 C22 1.382(4) 2_676 ? C26 H26A 0.9500 . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? N31 C35 1.351(3) . ? N31 N32 1.367(3) . ? N31 C47 1.453(3) . ? N32 C33 1.333(4) . ? C33 C34 1.386(4) . ? C33 C36 1.484(4) . ? C34 C35 1.370(4) . ? C34 H34A 0.9500 . ? C35 C37 1.478(4) . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C41 C46 1.381(3) . ? C41 C42 1.382(4) . ? C41 C47 1.511(4) . ? C42 C46 1.382(4) 2_756 ? C42 H42A 0.9500 . ? C46 C42 1.382(4) 2_756 ? C46 H46A 0.9500 . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? C51 C56 1.391(4) . ? C51 C52 1.395(4) . ? C51 C61 1.494(4) . ? C52 C53 1.395(4) . ? C52 C62 1.498(4) . ? C53 C54 1.394(4) . ? C53 C63 1.506(4) . ? C54 C55 1.399(4) . ? C54 C64A 1.509(4) . ? C55 C56 1.403(4) . ? C55 C65 1.504(4) . ? C56 C66 1.506(4) . ? C61 O62 1.193(3) . ? C61 O61 1.325(3) . ? O61 H61 0.91(3) . ? C62 H62A 0.9800 . ? C62 H62B 0.9800 . ? C62 H62C 0.9800 . ? C63 H63A 0.9800 . ? C63 H63B 0.9800 . ? C63 H63C 0.9800 . ? C64A H64A 0.9800 . ? C64A H64B 0.9800 . ? C64A H64C 0.9800 . ? C65 H65A 0.9800 . ? C65 H65B 0.9800 . ? C65 H65C 0.9800 . ? C66 H66A 0.9800 . ? C66 H66B 0.9800 . ? C66 H66C 0.9800 . ? C71 C76 1.389(4) . ? C71 C72 1.391(4) . ? C71 C81 1.501(4) . ? C72 C73 1.406(4) . ? C72 C82 1.497(4) . ? C73 C74 1.395(4) . ? C73 C83A 1.504(4) . ? C74 C75 1.400(4) . ? C74 C84 1.508(4) . ? C75 C76 1.401(4) . ? C75 C85 1.506(4) . ? C76 C86 1.499(4) . ? C81 O82 1.195(3) . ? C81 O81 1.310(3) . ? O81 H81 0.96(3) . ? C82 H82A 0.9800 . ? C82 H82B 0.9800 . ? C82 H82C 0.9800 . ? C83A H83A 0.9800 . ? C83A H83B 0.9800 . ? C83A H83C 0.9800 . ? C84 H84A 0.9800 . ? C84 H84B 0.9800 . ? C84 H84C 0.9800 . ? C85 H85A 0.9800 . ? C85 H85B 0.9800 . ? C85 H85C 0.9800 . ? C86 H86A 0.9800 . ? C86 H86B 0.9800 . ? C86 H86C 0.9800 . ? 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 N12 N11 C15 111.2(2) . . ? N12 N11 C27 119.3(2) . . ? C15 N11 C27 129.5(2) . . ? C13 N12 N11 106.2(2) . . ? N12 C13 C14 109.9(3) . . ? N12 C13 C16 120.4(2) . . ? C14 C13 C16 129.7(3) . . ? C15 C14 C13 106.3(3) . . ? C15 C14 H14A 126.9 . . ? C13 C14 H14A 126.9 . . ? N11 C15 C14 106.5(2) . . ? N11 C15 C17 123.4(3) . . ? C14 C15 C17 130.1(3) . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C26 C21 C22 118.2(3) . . ? C26 C21 C27 120.3(2) . . ? C22 C21 C27 121.5(2) . . ? C26 C22 C21 120.7(3) 2_676 . ? C26 C22 H22A 119.6 2_676 . ? C21 C22 H22A 119.6 . . ? C21 C26 C22 121.1(2) . 2_676 ? C21 C26 H26A 119.5 . . ? C22 C26 H26A 119.5 2_676 . ? N11 C27 C21 112.7(2) . . ? N11 C27 H27A 109.1 . . ? C21 C27 H27A 109.1 . . ? N11 C27 H27B 109.1 . . ? C21 C27 H27B 109.1 . . ? H27A C27 H27B 107.8 . . ? C35 N31 N32 111.5(2) . . ? C35 N31 C47 128.3(2) . . ? N32 N31 C47 120.1(2) . . ? C33 N32 N31 105.0(2) . . ? N32 C33 C34 110.7(2) . . ? N32 C33 C36 120.3(3) . . ? C34 C33 C36 129.0(3) . . ? C35 C34 C33 106.5(3) . . ? C35 C34 H34A 126.8 . . ? C33 C34 H34A 126.8 . . ? N31 C35 C34 106.3(2) . . ? N31 C35 C37 123.0(3) . . ? C34 C35 C37 130.6(3) . . ? C33 C36 H36A 109.5 . . ? C33 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C33 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C35 C37 H37A 109.5 . . ? C35 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C35 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C46 C41 C42 118.9(2) . . ? C46 C41 C47 120.9(2) . . ? C42 C41 C47 120.2(2) . . ? C46 C42 C41 120.5(2) 2_756 . ? C46 C42 H42A 119.7 2_756 . ? C41 C42 H42A 119.7 . . ? C41 C46 C42 120.5(3) . 2_756 ? C41 C46 H46A 119.7 . . ? C42 C46 H46A 119.7 2_756 . ? N31 C47 C41 112.6(2) . . ? N31 C47 H47A 109.1 . . ? C41 C47 H47A 109.1 . . ? N31 C47 H47B 109.1 . . ? C41 C47 H47B 109.1 . . ? H47A C47 H47B 107.8 . . ? C56 C51 C52 121.7(2) . . ? C56 C51 C61 118.8(3) . . ? C52 C51 C61 119.4(3) . . ? C51 C52 C53 118.7(3) . . ? C51 C52 C62 119.6(2) . . ? C53 C52 C62 121.7(3) . . ? C54 C53 C52 120.6(3) . . ? C54 C53 C63 119.6(2) . . ? C52 C53 C63 119.7(3) . . ? C53 C54 C55 120.1(2) . . ? C53 C54 C64A 120.5(3) . . ? C55 C54 C64A 119.4(3) . . ? C54 C55 C56 119.8(3) . . ? C54 C55 C65 121.0(3) . . ? C56 C55 C65 119.3(3) . . ? C51 C56 C55 119.1(3) . . ? C51 C56 C66 120.5(2) . . ? C55 C56 C66 120.4(3) . . ? O62 C61 O61 122.5(2) . . ? O62 C61 C51 123.6(3) . . ? O61 C61 C51 113.9(2) . . ? C61 O61 H61 108(2) . . ? C52 C62 H62A 109.5 . . ? C52 C62 H62B 109.5 . . ? H62A C62 H62B 109.5 . . ? C52 C62 H62C 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? C53 C63 H63A 109.5 . . ? C53 C63 H63B 109.5 . . ? H63A C63 H63B 109.5 . . ? C53 C63 H63C 109.5 . . ? H63A C63 H63C 109.5 . . ? H63B C63 H63C 109.5 . . ? C54 C64A H64A 109.5 . . ? C54 C64A H64B 109.5 . . ? H64A C64A H64B 109.5 . . ? C54 C64A H64C 109.5 . . ? H64A C64A H64C 109.5 . . ? H64B C64A H64C 109.5 . . ? C55 C65 H65A 109.5 . . ? C55 C65 H65B 109.5 . . ? H65A C65 H65B 109.5 . . ? C55 C65 H65C 109.5 . . ? H65A C65 H65C 109.5 . . ? H65B C65 H65C 109.5 . . ? C56 C66 H66A 109.5 . . ? C56 C66 H66B 109.5 . . ? H66A C66 H66B 109.5 . . ? C56 C66 H66C 109.5 . . ? H66A C66 H66C 109.5 . . ? H66B C66 H66C 109.5 . . ? C76 C71 C72 122.2(2) . . ? C76 C71 C81 119.4(3) . . ? C72 C71 C81 118.2(2) . . ? C71 C72 C73 119.0(3) . . ? C71 C72 C82 121.3(2) . . ? C73 C72 C82 119.7(3) . . ? C74 C73 C72 119.4(3) . . ? C74 C73 C83A 121.5(2) . . ? C72 C73 C83A 119.0(3) . . ? C73 C74 C75 120.6(2) . . ? C73 C74 C84 119.7(3) . . ? C75 C74 C84 119.6(3) . . ? C74 C75 C76 120.0(3) . . ? C74 C75 C85 120.1(3) . . ? C76 C75 C85 119.9(3) . . ? C71 C76 C75 118.5(3) . . ? C71 C76 C86 119.9(2) . . ? C75 C76 C86 121.6(3) . . ? O82 C81 O81 123.1(3) . . ? O82 C81 C71 122.0(2) . . ? O81 C81 C71 114.9(2) . . ? C81 O81 H81 107.5(18) . . ? C72 C82 H82A 109.5 . . ? C72 C82 H82B 109.5 . . ? H82A C82 H82B 109.5 . . ? C72 C82 H82C 109.5 . . ? H82A C82 H82C 109.5 . . ? H82B C82 H82C 109.5 . . ? C73 C83A H83A 109.5 . . ? C73 C83A H83B 109.5 . . ? H83A C83A H83B 109.5 . . ? C73 C83A H83C 109.5 . . ? H83A C83A H83C 109.5 . . ? H83B C83A H83C 109.5 . . ? C74 C84 H84A 109.5 . . ? C74 C84 H84B 109.5 . . ? H84A C84 H84B 109.5 . . ? C74 C84 H84C 109.5 . . ? H84A C84 H84C 109.5 . . ? H84B C84 H84C 109.5 . . ? C75 C85 H85A 109.5 . . ? C75 C85 H85B 109.5 . . ? H85A C85 H85B 109.5 . . ? C75 C85 H85C 109.5 . . ? H85A C85 H85C 109.5 . . ? H85B C85 H85C 109.5 . . ? C76 C86 H86A 109.5 . . ? C76 C86 H86B 109.5 . . ? H86A C86 H86B 109.5 . . ? C76 C86 H86C 109.5 . . ? H86A C86 H86C 109.5 . . ? H86B C86 H86C 109.5 . . ? 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 C15 N11 N12 C13 0.4(3) . . . . ? C27 N11 N12 C13 -179.0(2) . . . . ? N11 N12 C13 C14 -0.3(3) . . . . ? N11 N12 C13 C16 -178.7(2) . . . . ? N12 C13 C14 C15 0.1(3) . . . . ? C16 C13 C14 C15 178.3(3) . . . . ? N12 N11 C15 C14 -0.4(3) . . . . ? C27 N11 C15 C14 179.1(2) . . . . ? N12 N11 C15 C17 -179.8(3) . . . . ? C27 N11 C15 C17 -0.4(4) . . . . ? C13 C14 C15 N11 0.1(3) . . . . ? C13 C14 C15 C17 179.5(3) . . . . ? C26 C21 C22 C26 0.3(5) . . . 2_676 ? C27 C21 C22 C26 -177.7(3) . . . 2_676 ? C22 C21 C26 C22 -0.3(5) . . . 2_676 ? C27 C21 C26 C22 177.8(3) . . . 2_676 ? N12 N11 C27 C21 -76.8(3) . . . . ? C15 N11 C27 C21 103.8(3) . . . . ? C26 C21 C27 N11 116.1(3) . . . . ? C22 C21 C27 N11 -65.9(3) . . . . ? C35 N31 N32 C33 0.0(3) . . . . ? C47 N31 N32 C33 176.4(2) . . . . ? N31 N32 C33 C34 0.7(3) . . . . ? N31 N32 C33 C36 -177.1(2) . . . . ? N32 C33 C34 C35 -1.1(3) . . . . ? C36 C33 C34 C35 176.4(3) . . . . ? N32 N31 C35 C34 -0.7(3) . . . . ? C47 N31 C35 C34 -176.6(2) . . . . ? N32 N31 C35 C37 178.0(3) . . . . ? C47 N31 C35 C37 2.0(4) . . . . ? C33 C34 C35 N31 1.0(3) . . . . ? C33 C34 C35 C37 -177.5(3) . . . . ? C46 C41 C42 C46 -0.1(5) . . . 2_756 ? C47 C41 C42 C46 179.1(2) . . . 2_756 ? C42 C41 C46 C42 0.1(5) . . . 2_756 ? C47 C41 C46 C42 -179.1(2) . . . 2_756 ? C35 N31 C47 C41 73.7(3) . . . . ? N32 N31 C47 C41 -102.0(3) . . . . ? C46 C41 C47 N31 71.8(3) . . . . ? C42 C41 C47 N31 -107.4(3) . . . . ? C56 C51 C52 C53 0.1(4) . . . . ? C61 C51 C52 C53 175.2(2) . . . . ? C56 C51 C52 C62 -179.3(3) . . . . ? C61 C51 C52 C62 -4.3(4) . . . . ? C51 C52 C53 C54 0.5(4) . . . . ? C62 C52 C53 C54 180.0(3) . . . . ? C51 C52 C53 C63 -177.5(2) . . . . ? C62 C52 C53 C63 1.9(4) . . . . ? C52 C53 C54 C55 -0.5(4) . . . . ? C63 C53 C54 C55 177.5(2) . . . . ? C52 C53 C54 C64A -179.7(3) . . . . ? C63 C53 C54 C64A -1.7(4) . . . . ? C53 C54 C55 C56 -0.2(4) . . . . ? C64A C54 C55 C56 179.1(3) . . . . ? C53 C54 C55 C65 -179.2(3) . . . . ? C64A C54 C55 C65 0.1(4) . . . . ? C52 C51 C56 C55 -0.8(4) . . . . ? C61 C51 C56 C55 -175.9(2) . . . . ? C52 C51 C56 C66 -180.0(3) . . . . ? C61 C51 C56 C66 4.9(4) . . . . ? C54 C55 C56 C51 0.8(4) . . . . ? C65 C55 C56 C51 179.8(3) . . . . ? C54 C55 C56 C66 180.0(3) . . . . ? C65 C55 C56 C66 -1.0(4) . . . . ? C56 C51 C61 O62 86.0(4) . . . . ? C52 C51 C61 O62 -89.2(4) . . . . ? C56 C51 C61 O61 -92.4(3) . . . . ? C52 C51 C61 O61 92.3(3) . . . . ? C76 C71 C72 C73 -2.2(4) . . . . ? C81 C71 C72 C73 173.0(2) . . . . ? C76 C71 C72 C82 178.3(3) . . . . ? C81 C71 C72 C82 -6.5(4) . . . . ? C71 C72 C73 C74 0.0(4) . . . . ? C82 C72 C73 C74 179.4(2) . . . . ? C71 C72 C73 C83A -179.5(2) . . . . ? C82 C72 C73 C83A 0.0(4) . . . . ? C72 C73 C74 C75 3.3(4) . . . . ? C83A C73 C74 C75 -177.3(3) . . . . ? C72 C73 C74 C84 -177.1(3) . . . . ? C83A C73 C74 C84 2.4(4) . . . . ? C73 C74 C75 C76 -4.4(4) . . . . ? C84 C74 C75 C76 176.0(3) . . . . ? C73 C74 C75 C85 176.2(2) . . . . ? C84 C74 C75 C85 -3.4(4) . . . . ? C72 C71 C76 C75 1.2(4) . . . . ? C81 C71 C76 C75 -174.0(2) . . . . ? C72 C71 C76 C86 -178.5(3) . . . . ? C81 C71 C76 C86 6.4(4) . . . . ? C74 C75 C76 C71 2.1(4) . . . . ? C85 C75 C76 C71 -178.5(2) . . . . ? C74 C75 C76 C86 -178.2(3) . . . . ? C85 C75 C76 C86 1.2(4) . . . . ? C76 C71 C81 O82 89.9(4) . . . . ? C72 C71 C81 O82 -85.5(4) . . . . ? C76 C71 C81 O81 -90.1(3) . . . . ? C72 C71 C81 O81 94.6(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 O61 H61 N12 0.91(3) 1.78(3) 2.675(3) 164(3) . O81 H81 N32 0.96(3) 1.72(3) 2.667(3) 169(3) . _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.310 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.082 #END