data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Makoto Obata' _publ_contact_author_address ; Graduate School of Humanities and Sciences Nara Women's University Kitauoyanishimachi Nara 630-8506 JAPAN ; _publ_contact_author_email MOBATA@CC.NARA-WU.AC.JP _publ_section_title ; Syntheses, structural characterization and photophysical properties of 4-(2-pyridyl)-1,2,3-triazole rhenium(I) complexes ; loop_ _publ_author_name 'Makoto Obata' 'Justyna A. Czaplewska' 'Takuzo Funabiki' 'Masafumi Harada' 'Hideki Hashimoto' ; C.Kameyama ; 'Isamu Kinoshita' 'Asuka Kitamura' 'Toshiyuki Kusumoto' 'Yuji Mikata' 'Akemi Mori' 'Rika Tanaka' ; S.Yano ; #============================================================================== data___bnpyta2 _database_code_depnum_ccdc_archive 'CCDC 633046' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C14 H12 N4 ' _chemical_formula_moiety 'C14 H12 N4 ' _chemical_formula_weight 236.28 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'F d d 2' _symmetry_space_group_name_Hall 'F 2 -2d' _symmetry_Int_Tables_number 43 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/4-X,1/4+Y,1/4+Z 3 1/4+X,1/4-Y,1/4+Z 4 1/2-X,-Y,1/2+Z 5 +X,1/2+Y,1/2+Z 6 1/4-X,3/4+Y,3/4+Z 7 1/4+X,3/4-Y,3/4+Z 8 1/2-X,1/2-Y,+Z 9 1/2+X,+Y,1/2+Z 10 3/4-X,1/4+Y,3/4+Z 11 3/4+X,1/4-Y,3/4+Z 12 -X,-Y,+Z 13 1/2+X,1/2+Y,+Z 14 3/4-X,3/4+Y,1/4+Z 15 3/4+X,3/4-Y,1/4+Z 16 -X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 28.4093(11) _cell_length_b 29.0074(15) _cell_length_c 5.7657(2) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 4751.4(3) _cell_formula_units_Z 16 _cell_measurement_reflns_used 3138 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 173.1 #------------------------------------------------------------------------------ _exptl_crystal_description chip _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1984.00 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Higashi, T. (1999). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_T_max 0.984 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_reflns_number 11614 _diffrn_reflns_av_R_equivalents 0.021 _diffrn_reflns_theta_max 27.47 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 1503 _reflns_number_gt 1388 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0353 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 1503 _refine_ls_number_parameters 175 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.0004Fo^2^ + 1.0000\s(Fo^2^)]' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.57 _refine_diff_density_min -0.25 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 N(1) N 0.57838(5) -0.01673(4) 0.6060(2) 0.0332(3) Uani 1.00 1 d . . . N(2) N 0.56458(4) 0.07929(5) 0.2050(2) 0.0309(3) Uani 1.00 1 d . . . N(3) N 0.56386(5) 0.12337(5) 0.2603(2) 0.0320(3) Uani 1.00 1 d . . . N(4) N 0.56469(4) 0.12590(4) 0.4946(2) 0.0277(3) Uani 1.00 1 d . . . C(1) C 0.57845(6) -0.06291(6) 0.6126(3) 0.0399(4) Uani 1.00 1 d . . . C(2) C 0.56621(6) -0.09054(6) 0.4278(3) 0.0399(4) Uani 1.00 1 d . . . C(3) C 0.55422(6) -0.06961(6) 0.2221(3) 0.0407(4) Uani 1.00 1 d . . . C(4) C 0.55515(5) -0.02183(6) 0.2062(3) 0.0330(4) Uani 1.00 1 d . . . C(5) C 0.56666(5) 0.00316(5) 0.4038(3) 0.0269(3) Uani 1.00 1 d . . . C(6) C 0.56600(5) 0.05393(5) 0.4042(3) 0.0258(3) Uani 1.00 1 d . . . C(7) C 0.56604(5) 0.08362(5) 0.5898(3) 0.0273(3) Uani 1.00 1 d . . . C(8) C 0.56057(5) 0.17060(5) 0.6101(3) 0.0320(4) Uani 1.00 1 d . . . C(9) C 0.50975(5) 0.18520(4) 0.6386(2) 0.0255(3) Uani 1.00 1 d . . . C(10) C 0.48721(5) 0.20991(4) 0.4653(2) 0.0269(3) Uani 1.00 1 d . . . C(11) C 0.44043(5) 0.22278(5) 0.4915(3) 0.0296(3) Uani 1.00 1 d . . . C(12) C 0.41612(5) 0.21099(5) 0.6916(3) 0.0316(4) Uani 1.00 1 d . . . C(13) C 0.43849(5) 0.18644(5) 0.8644(3) 0.0324(3) Uani 1.00 1 d . . . C(14) C 0.48534(5) 0.17371(5) 0.8399(2) 0.0299(3) Uani 1.00 1 d . . . H(1) H 0.5874 -0.0774 0.7538 0.048 Uiso 1.00 1 c R . . H(2) H 0.5663 -0.1232 0.4410 0.048 Uiso 1.00 1 c R . . H(3) H 0.5452 -0.0877 0.0921 0.049 Uiso 1.00 1 c R . . H(4) H 0.5481 -0.0066 0.0646 0.039 Uiso 1.00 1 c R . . H(5) H 0.5668 0.0759 0.7499 0.033 Uiso 1.00 1 c R . . H(6) H 0.5747 0.1687 0.7590 0.038 Uiso 1.00 1 c R . . H(7) H 0.5766 0.1930 0.5196 0.038 Uiso 1.00 1 c R . . H(8) H 0.5037 0.2178 0.3275 0.032 Uiso 1.00 1 c R . . H(9) H 0.4249 0.2398 0.3733 0.035 Uiso 1.00 1 c R . . H(10) H 0.3842 0.2201 0.7101 0.038 Uiso 1.00 1 c R . . H(11) H 0.4216 0.1781 1.0003 0.039 Uiso 1.00 1 c R . . H(12) H 0.5008 0.1571 0.9595 0.036 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N(1) 0.0394(6) 0.0286(6) 0.0318(7) 0.0013(5) 0.0016(6) 0.0007(6) N(2) 0.0338(7) 0.0298(6) 0.0291(7) 0.0033(5) 0.0003(6) -0.0002(5) N(3) 0.0348(7) 0.0301(7) 0.0311(7) 0.0043(5) 0.0003(5) 0.0016(6) N(4) 0.0267(6) 0.0245(6) 0.0318(7) 0.0039(4) -0.0024(5) -0.0013(5) C(1) 0.0465(8) 0.0308(7) 0.0423(10) 0.0007(7) 0.0095(9) 0.0056(8) C(2) 0.0416(8) 0.0267(7) 0.0515(12) -0.0059(6) 0.0185(8) -0.0037(8) C(3) 0.0395(8) 0.0349(8) 0.0478(11) -0.0104(7) 0.0109(8) -0.0145(8) C(4) 0.0337(7) 0.0339(8) 0.0314(9) -0.0040(6) 0.0033(7) -0.0065(7) C(5) 0.0234(6) 0.0270(6) 0.0302(7) 0.0003(5) 0.0047(6) -0.0035(7) C(6) 0.0227(6) 0.0282(7) 0.0266(7) 0.0013(5) -0.0002(5) -0.0022(7) C(7) 0.0286(7) 0.0254(7) 0.0279(8) 0.0037(5) -0.0017(6) -0.0014(6) C(8) 0.0274(6) 0.0243(7) 0.0444(10) 0.0004(5) -0.0045(7) -0.0073(7) C(9) 0.0270(6) 0.0175(5) 0.0319(7) -0.0007(4) -0.0037(6) -0.0036(6) C(10) 0.0334(7) 0.0202(6) 0.0272(7) -0.0021(5) 0.0019(6) -0.0000(6) C(11) 0.0324(7) 0.0233(7) 0.0331(8) 0.0022(5) -0.0055(6) 0.0021(6) C(12) 0.0266(7) 0.0293(7) 0.0390(10) -0.0004(5) 0.0005(7) -0.0050(7) C(13) 0.0363(7) 0.0329(7) 0.0279(8) -0.0052(6) 0.0038(7) -0.0006(7) C(14) 0.0355(7) 0.0257(7) 0.0284(8) -0.0007(5) -0.0064(7) 0.0010(6) #============================================================================== _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution SIR92 _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 N(1) C(1) 1.340(2) yes . . N(1) C(5) 1.343(2) yes . . N(2) N(3) 1.318(2) yes . . N(2) C(6) 1.365(2) yes . . N(3) N(4) 1.353(2) yes . . N(4) C(7) 1.3442(19) yes . . N(4) C(8) 1.462(2) yes . . C(1) C(2) 1.378(2) yes . . C(2) C(3) 1.376(2) yes . . C(3) C(4) 1.389(2) yes . . C(4) C(5) 1.389(2) yes . . C(5) C(6) 1.473(2) yes . . C(6) C(7) 1.374(2) yes . . C(8) C(9) 1.514(2) yes . . C(9) C(10) 1.386(2) yes . . C(9) C(14) 1.393(2) yes . . C(10) C(11) 1.389(2) yes . . C(11) C(12) 1.388(2) yes . . C(12) C(13) 1.380(2) yes . . C(13) C(14) 1.388(2) yes . . C(1) H(1) 0.950 no . . C(2) H(2) 0.950 no . . C(3) H(3) 0.950 no . . C(4) H(4) 0.950 no . . C(7) H(5) 0.950 no . . C(8) H(6) 0.950 no . . C(8) H(7) 0.950 no . . C(10) H(8) 0.950 no . . C(11) H(9) 0.950 no . . C(12) H(10) 0.950 no . . C(13) H(11) 0.950 no . . C(14) H(12) 0.950 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(1) N(1) C(5) 117.04(15) yes . . . N(3) N(2) C(6) 108.65(13) yes . . . N(2) N(3) N(4) 107.10(13) yes . . . N(3) N(4) C(7) 111.02(12) yes . . . N(3) N(4) C(8) 120.09(13) yes . . . C(7) N(4) C(8) 128.71(15) yes . . . N(1) C(1) C(2) 123.99(18) yes . . . C(1) C(2) C(3) 118.21(16) yes . . . C(2) C(3) C(4) 119.49(17) yes . . . C(3) C(4) C(5) 118.11(16) yes . . . N(1) C(5) C(4) 123.10(13) yes . . . N(1) C(5) C(6) 115.57(14) yes . . . C(4) C(5) C(6) 121.32(15) yes . . . N(2) C(6) C(5) 122.57(14) yes . . . N(2) C(6) C(7) 108.53(13) yes . . . C(5) C(6) C(7) 128.90(15) yes . . . N(4) C(7) C(6) 104.71(14) yes . . . N(4) C(8) C(9) 111.95(11) yes . . . C(8) C(9) C(10) 120.48(14) yes . . . C(8) C(9) C(14) 119.89(13) yes . . . C(10) C(9) C(14) 119.62(13) yes . . . C(9) C(10) C(11) 120.20(14) yes . . . C(10) C(11) C(12) 120.02(14) yes . . . C(11) C(12) C(13) 119.90(13) yes . . . C(12) C(13) C(14) 120.34(15) yes . . . C(9) C(14) C(13) 119.92(14) yes . . . N(1) C(1) H(1) 117.7 no . . . C(2) C(1) H(1) 118.3 no . . . C(1) C(2) H(2) 121.1 no . . . C(3) C(2) H(2) 120.7 no . . . C(2) C(3) H(3) 120.2 no . . . C(4) C(3) H(3) 120.3 no . . . C(3) C(4) H(4) 121.2 no . . . C(5) C(4) H(4) 120.7 no . . . N(4) C(7) H(5) 127.8 no . . . C(6) C(7) H(5) 127.5 no . . . N(4) C(8) H(6) 109.0 no . . . N(4) C(8) H(7) 108.5 no . . . C(9) C(8) H(6) 108.9 no . . . C(9) C(8) H(7) 109.0 no . . . H(6) C(8) H(7) 109.5 no . . . C(9) C(10) H(8) 120.0 no . . . C(11) C(10) H(8) 119.8 no . . . C(10) C(11) H(9) 120.4 no . . . C(12) C(11) H(9) 119.5 no . . . C(11) C(12) H(10) 120.0 no . . . C(13) C(12) H(10) 120.1 no . . . C(12) C(13) H(11) 119.6 no . . . C(14) C(13) H(11) 120.0 no . . . C(9) C(14) H(12) 119.8 no . . . C(13) C(14) H(12) 120.3 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C(1) N(1) C(5) C(4) -0.3(2) ? . . . . C(1) N(1) C(5) C(6) 178.79(13) ? . . . . C(5) N(1) C(1) C(2) -1.7(2) ? . . . . N(3) N(2) C(6) C(5) 179.42(13) ? . . . . N(3) N(2) C(6) C(7) 0.15(16) ? . . . . C(6) N(2) N(3) N(4) -0.17(15) ? . . . . N(2) N(3) N(4) C(7) 0.13(15) ? . . . . N(2) N(3) N(4) C(8) -175.35(11) ? . . . . N(3) N(4) C(7) C(6) -0.04(12) ? . . . . N(3) N(4) C(8) C(9) 84.23(17) ? . . . . C(7) N(4) C(8) C(9) -90.36(18) ? . . . . C(8) N(4) C(7) C(6) 174.95(12) ? . . . . N(1) C(1) C(2) C(3) 1.6(2) ? . . . . C(1) C(2) C(3) C(4) 0.5(2) ? . . . . C(2) C(3) C(4) C(5) -2.3(2) ? . . . . C(3) C(4) C(5) N(1) 2.3(2) ? . . . . C(3) C(4) C(5) C(6) -176.79(14) ? . . . . N(1) C(5) C(6) N(2) 165.95(13) ? . . . . N(1) C(5) C(6) C(7) -14.9(2) ? . . . . C(4) C(5) C(6) N(2) -14.9(2) ? . . . . C(4) C(5) C(6) C(7) 164.19(15) ? . . . . N(2) C(6) C(7) N(4) -0.07(12) ? . . . . C(5) C(6) C(7) N(4) -179.27(13) ? . . . . N(4) C(8) C(9) C(10) -88.40(16) ? . . . . N(4) C(8) C(9) C(14) 91.49(18) ? . . . . C(8) C(9) C(10) C(11) 179.32(12) ? . . . . C(8) C(9) C(14) C(13) -178.95(13) ? . . . . C(10) C(9) C(14) C(13) 0.9(2) ? . . . . C(14) C(9) C(10) C(11) -0.57(19) ? . . . . C(9) C(10) C(11) C(12) 0.1(2) ? . . . . C(10) C(11) C(12) C(13) -0.05(17) ? . . . . C(11) C(12) C(13) C(14) 0.4(2) ? . . . . C(12) C(13) C(14) C(9) -0.9(2) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 N(1) C(4) 3.526(2) ? . 1_556 N(1) C(11) 3.517(2) ? . 3_555 N(1) C(12) 3.546(2) ? . 3_555 N(2) C(3) 3.388(2) ? . 12_655 N(2) C(7) 3.549(2) ? . 1_554 N(2) C(12) 3.4630(19) ? . 3_554 N(2) C(13) 3.5879(18) ? . 3_554 C(1) C(3) 3.586(2) ? . 1_556 C(1) C(8) 3.506(2) ? . 6_644 C(2) C(8) 3.537(2) ? . 6_644 C(3) N(2) 3.388(2) ? . 12_655 C(3) C(1) 3.586(2) ? . 1_554 C(4) N(1) 3.526(2) ? . 1_554 C(4) C(4) 3.380(2) ? . 12_655 C(7) N(2) 3.549(2) ? . 1_556 C(8) C(1) 3.506(2) ? . 2_655 C(8) C(2) 3.537(2) ? . 2_655 C(9) C(10) 3.5797(18) ? . 16_655 C(10) C(9) 3.5797(18) ? . 16_654 C(10) C(14) 3.5395(18) ? . 16_654 C(11) N(1) 3.517(2) ? . 11_454 C(12) N(1) 3.546(2) ? . 11_454 C(12) N(2) 3.4630(19) ? . 11_455 C(13) N(2) 3.5879(18) ? . 11_455 C(14) C(10) 3.5395(18) ? . 16_655 N(1) H(4) 2.796 ? . 1_556 N(1) H(6) 3.376 ? . 6_644 N(1) H(7) 3.523 ? . 6_644 N(1) H(9) 2.853 ? . 3_555 N(1) H(10) 2.918 ? . 3_555 N(2) H(3) 3.195 ? . 12_655 N(2) H(5) 2.627 ? . 1_554 N(2) H(10) 2.821 ? . 3_554 N(2) H(11) 3.059 ? . 3_554 N(2) H(12) 3.221 ? . 1_554 N(3) H(1) 3.478 ? . 2_654 N(3) H(3) 3.407 ? . 12_655 N(3) H(5) 3.251 ? . 1_554 N(3) H(6) 3.190 ? . 1_554 N(3) H(11) 3.406 ? . 3_554 N(3) H(12) 2.678 ? . 1_554 N(4) H(2) 3.565 ? . 2_655 C(1) H(3) 3.009 ? . 1_556 C(1) H(4) 3.194 ? . 1_556 C(1) H(6) 2.864 ? . 6_644 C(1) H(7) 3.348 ? . 6_644 C(1) H(9) 3.465 ? . 3_555 C(2) H(6) 3.144 ? . 6_644 C(2) H(7) 3.324 ? . 6_644 C(2) H(11) 3.556 ? . 12_654 C(3) H(1) 2.869 ? . 1_554 C(3) H(7) 3.416 ? . 6_644 C(3) H(11) 3.466 ? . 12_654 C(3) H(12) 3.343 ? . 12_654 C(4) H(1) 3.200 ? . 1_554 C(4) H(4) 3.155 ? . 12_655 C(4) H(7) 3.529 ? . 6_644 C(4) H(10) 3.052 ? . 3_554 C(5) H(7) 3.583 ? . 6_644 C(5) H(9) 3.331 ? . 3_555 C(5) H(10) 3.291 ? . 3_554 C(6) H(9) 3.574 ? . 3_555 C(6) H(10) 3.286 ? . 3_554 C(6) H(11) 3.172 ? . 3_554 C(7) H(10) 3.276 ? . 3_555 C(7) H(11) 3.597 ? . 3_554 C(8) H(9) 3.038 ? . 16_655 C(9) H(2) 3.034 ? . 12_655 C(9) H(8) 3.041 ? . 16_655 C(9) H(9) 3.165 ? . 16_655 C(10) H(2) 2.943 ? . 12_655 C(10) H(8) 2.971 ? . 16_655 C(10) H(11) 3.393 ? . 1_554 C(10) H(12) 3.317 ? . 1_554 C(11) H(2) 2.910 ? . 12_655 C(11) H(6) 3.449 ? . 16_654 C(11) H(8) 3.041 ? . 16_655 C(11) H(11) 3.160 ? . 1_554 C(12) H(2) 2.970 ? . 12_655 C(12) H(5) 3.214 ? . 11_454 C(12) H(7) 3.373 ? . 16_655 C(12) H(8) 3.174 ? . 16_655 C(13) H(1) 3.311 ? . 12_655 C(13) H(2) 3.057 ? . 12_655 C(13) H(3) 3.185 ? . 12_656 C(13) H(8) 3.374 ? . 1_556 C(13) H(8) 3.235 ? . 16_655 C(13) H(9) 3.339 ? . 1_556 C(14) H(1) 3.512 ? . 12_655 C(14) H(2) 3.097 ? . 12_655 C(14) H(3) 3.015 ? . 12_656 C(14) H(8) 3.132 ? . 1_556 C(14) H(8) 3.164 ? . 16_655 C(14) H(9) 3.583 ? . 16_655 H(1) N(3) 3.478 ? . 6_645 H(1) C(3) 2.869 ? . 1_556 H(1) C(4) 3.200 ? . 1_556 H(1) C(13) 3.311 ? . 12_655 H(1) C(14) 3.512 ? . 12_655 H(1) H(3) 2.310 ? . 1_556 H(1) H(4) 2.945 ? . 1_556 H(1) H(6) 2.869 ? . 6_644 H(1) H(10) 3.587 ? . 3_555 H(1) H(11) 3.260 ? . 12_655 H(2) N(4) 3.565 ? . 6_644 H(2) C(9) 3.034 ? . 12_655 H(2) C(10) 2.943 ? . 12_655 H(2) C(11) 2.910 ? . 12_655 H(2) C(12) 2.970 ? . 12_655 H(2) C(13) 3.057 ? . 12_655 H(2) C(14) 3.097 ? . 12_655 H(2) H(6) 3.347 ? . 6_644 H(2) H(8) 3.451 ? . 12_655 H(2) H(9) 3.414 ? . 12_655 H(2) H(10) 3.504 ? . 12_655 H(2) H(11) 3.019 ? . 12_654 H(2) H(12) 3.509 ? . 12_654 H(3) N(2) 3.195 ? . 12_655 H(3) N(3) 3.407 ? . 12_655 H(3) C(1) 3.009 ? . 1_554 H(3) C(13) 3.185 ? . 12_654 H(3) C(14) 3.015 ? . 12_654 H(3) H(1) 2.310 ? . 1_554 H(3) H(11) 2.837 ? . 12_654 H(3) H(12) 2.519 ? . 12_654 H(4) N(1) 2.796 ? . 1_554 H(4) C(1) 3.194 ? . 1_554 H(4) C(4) 3.155 ? . 12_655 H(4) H(1) 2.945 ? . 1_554 H(4) H(4) 2.761 ? . 12_655 H(4) H(5) 3.049 ? . 1_554 H(4) H(10) 2.732 ? . 3_554 H(5) N(2) 2.627 ? . 1_556 H(5) N(3) 3.251 ? . 1_556 H(5) C(12) 3.214 ? . 3_555 H(5) H(4) 3.049 ? . 1_556 H(5) H(10) 2.629 ? . 3_555 H(6) N(1) 3.376 ? . 2_655 H(6) N(3) 3.190 ? . 1_556 H(6) C(1) 2.864 ? . 2_655 H(6) C(2) 3.144 ? . 2_655 H(6) C(11) 3.449 ? . 16_655 H(6) H(1) 2.869 ? . 2_655 H(6) H(2) 3.347 ? . 2_655 H(6) H(9) 2.736 ? . 16_655 H(7) N(1) 3.523 ? . 2_655 H(7) C(1) 3.348 ? . 2_655 H(7) C(2) 3.324 ? . 2_655 H(7) C(3) 3.416 ? . 2_655 H(7) C(4) 3.529 ? . 2_655 H(7) C(5) 3.583 ? . 2_655 H(7) C(12) 3.373 ? . 16_654 H(7) H(9) 2.822 ? . 16_655 H(7) H(10) 3.283 ? . 16_654 H(8) C(9) 3.041 ? . 16_654 H(8) C(10) 2.971 ? . 16_654 H(8) C(11) 3.041 ? . 16_654 H(8) C(12) 3.174 ? . 16_654 H(8) C(13) 3.374 ? . 1_554 H(8) C(13) 3.235 ? . 16_654 H(8) C(14) 3.132 ? . 1_554 H(8) C(14) 3.164 ? . 16_654 H(8) H(2) 3.451 ? . 12_655 H(8) H(8) 3.442 ? . 16_654 H(8) H(8) 3.442 ? . 16_655 H(8) H(9) 3.535 ? . 16_654 H(8) H(11) 3.212 ? . 1_554 H(8) H(12) 2.758 ? . 1_554 H(9) N(1) 2.853 ? . 11_454 H(9) C(1) 3.465 ? . 11_454 H(9) C(5) 3.331 ? . 11_454 H(9) C(6) 3.574 ? . 11_454 H(9) C(8) 3.038 ? . 16_654 H(9) C(9) 3.165 ? . 16_654 H(9) C(13) 3.339 ? . 1_554 H(9) C(14) 3.583 ? . 16_654 H(9) H(2) 3.414 ? . 12_655 H(9) H(6) 2.736 ? . 16_654 H(9) H(7) 2.822 ? . 16_654 H(9) H(8) 3.535 ? . 16_655 H(9) H(11) 2.799 ? . 1_554 H(10) N(1) 2.918 ? . 11_454 H(10) N(2) 2.821 ? . 11_455 H(10) C(4) 3.052 ? . 11_455 H(10) C(5) 3.291 ? . 11_455 H(10) C(6) 3.286 ? . 11_455 H(10) C(7) 3.276 ? . 11_454 H(10) H(1) 3.587 ? . 11_454 H(10) H(2) 3.504 ? . 12_655 H(10) H(4) 2.732 ? . 11_455 H(10) H(5) 2.629 ? . 11_454 H(10) H(7) 3.283 ? . 16_655 H(11) N(2) 3.059 ? . 11_455 H(11) N(3) 3.406 ? . 11_455 H(11) C(2) 3.556 ? . 12_656 H(11) C(3) 3.466 ? . 12_656 H(11) C(6) 3.172 ? . 11_455 H(11) C(7) 3.597 ? . 11_455 H(11) C(10) 3.393 ? . 1_556 H(11) C(11) 3.160 ? . 1_556 H(11) H(1) 3.260 ? . 12_655 H(11) H(2) 3.019 ? . 12_656 H(11) H(3) 2.837 ? . 12_656 H(11) H(8) 3.212 ? . 1_556 H(11) H(9) 2.799 ? . 1_556 H(12) N(2) 3.221 ? . 1_556 H(12) N(3) 2.678 ? . 1_556 H(12) C(3) 3.343 ? . 12_656 H(12) C(10) 3.317 ? . 1_556 H(12) H(2) 3.509 ? . 12_656 H(12) H(3) 2.519 ? . 12_656 H(12) H(8) 2.758 ? . 1_556 #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== # Attachment 'ReBnpyta_rev.cif' data_crystalclear _database_code_depnum_ccdc_archive 'CCDC 633047' _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C17 H12 Cl N4 O3 Re' _chemical_formula_sum 'C17 H12 Cl N4 O3 Re' _chemical_formula_weight 541.96 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' Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.6557(5) _cell_length_b 20.5809(15) _cell_length_c 13.0676(11) _cell_angle_alpha 90.00 _cell_angle_beta 98.876(4) _cell_angle_gamma 90.00 _cell_volume 1768.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 5087 _cell_measurement_theta_min 4.0673 _cell_measurement_theta_max 27.4835 _exptl_crystal_description Needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.035 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 7.047 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.3331 _exptl_absorpt_correction_T_max 0.8164 _exptl_absorpt_process_details '(Jacobson, 1998)' _exptl_special_details ; ? ; _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_measurement_device_type 'Rigaku/MSC Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.6199 _diffrn_reflns_number 14028 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.19 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.772 _refine_diff_density_min -0.822 _refine_diff_density_rms 0.127 _reflns_number_total 4011 _reflns_number_gt 3716 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2001)' _computing_cell_refinement CrystalClear _computing_data_reduction ? _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material SHELXL97 _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^)+(0.0000P)^2^+25.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4011 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.0774 _refine_ls_wR_factor_gt 0.0744 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 Re1 Re 0.39498(4) 0.122284(12) 0.14835(2) 0.01939(8) Uani 1 1 d . . . Cl1 Cl 0.2343(3) 0.22873(9) 0.16913(14) 0.0327(4) Uani 1 1 d . . . N1 N 0.1816(7) 0.1185(3) 0.0024(4) 0.0212(11) Uani 1 1 d . . . N2 N 0.5357(8) 0.1761(3) 0.0398(4) 0.0206(11) Uani 1 1 d . . . N3 N 0.7027(8) 0.2113(3) 0.0536(4) 0.0219(11) Uani 1 1 d . . . N4 N 0.7022(8) 0.2422(3) -0.0368(4) 0.0220(11) Uani 1 1 d . . . O1 O 0.6176(9) -0.0030(3) 0.1147(5) 0.0504(16) Uani 1 1 d . . . O2 O 0.1210(8) 0.0509(3) 0.2806(5) 0.0450(15) Uani 1 1 d . . . O3 O 0.7268(8) 0.1491(3) 0.3332(4) 0.0397(13) Uani 1 1 d . . . C1 C 0.0012(10) 0.0880(3) -0.0117(6) 0.0265(14) Uani 1 1 d . . . H1A H -0.0381 0.0646 0.0446 0.032 Uiso 1 1 calc R . . C2 C -0.1294(10) 0.0892(4) -0.1045(7) 0.0342(17) Uani 1 1 d . . . H2A H -0.2552 0.0666 -0.1113 0.041 Uiso 1 1 calc R . . C3 C -0.0773(11) 0.1233(4) -0.1870(6) 0.0363(17) Uani 1 1 d . . . H3A H -0.1664 0.1247 -0.2511 0.044 Uiso 1 1 calc R . . C4 C 0.1075(11) 0.1556(4) -0.1749(6) 0.0327(16) Uani 1 1 d . . . H4A H 0.1468 0.1798 -0.2304 0.039 Uiso 1 1 calc R . . C5 C 0.2341(9) 0.1519(3) -0.0803(5) 0.0217(13) Uani 1 1 d . . . C6 C 0.4304(9) 0.1850(3) -0.0567(5) 0.0204(13) Uani 1 1 d . . . C7 C 0.5367(10) 0.2282(3) -0.1081(5) 0.0249(14) Uani 1 1 d . . . H7A H 0.5029 0.2443 -0.1767 0.030 Uiso 1 1 calc R . . C8 C 0.8619(10) 0.2903(3) -0.0447(5) 0.0261(14) Uani 1 1 d . . . H8A H 0.8634 0.3008 -0.1185 0.031 Uiso 1 1 calc R . . H8B H 0.9959 0.2716 -0.0161 0.031 Uiso 1 1 calc R . . C9 C 0.8285(10) 0.3521(3) 0.0134(5) 0.0240(14) Uani 1 1 d . . . C10 C 0.6377(11) 0.3746(4) 0.0248(6) 0.0386(17) Uani 1 1 d . . . H10A H 0.5213 0.3500 -0.0031 0.046 Uiso 1 1 calc R . . C11 C 0.6126(13) 0.4318(4) 0.0754(7) 0.0413(19) Uani 1 1 d . . . H11A H 0.4799 0.4467 0.0816 0.050 Uiso 1 1 calc R . . C12 C 0.7804(15) 0.4673(4) 0.1172(8) 0.052(2) Uani 1 1 d . . . H12A H 0.7655 0.5064 0.1539 0.063 Uiso 1 1 calc R . . C13 C 0.9695(15) 0.4453(5) 0.1051(10) 0.074(4) Uani 1 1 d . . . H13A H 1.0859 0.4701 0.1323 0.088 Uiso 1 1 calc R . . C14 C 0.9945(13) 0.3875(4) 0.0539(8) 0.056(3) Uani 1 1 d . . . H14A H 1.1270 0.3727 0.0471 0.067 Uiso 1 1 calc R . . C15 C 0.5353(10) 0.0409(3) 0.1221(6) 0.0287(16) Uani 1 1 d . . . C16 C 0.2265(10) 0.0777(3) 0.2326(6) 0.0266(14) Uani 1 1 d . . . C17 C 0.6003(10) 0.1377(3) 0.2656(6) 0.0268(14) 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 Re1 0.02178(12) 0.01720(12) 0.01944(12) 0.00039(11) 0.00398(8) 0.00022(11) Cl1 0.0396(9) 0.0319(9) 0.0259(9) -0.0018(7) 0.0032(7) 0.0078(7) N1 0.020(2) 0.018(3) 0.026(3) -0.006(2) 0.005(2) 0.001(2) N2 0.021(2) 0.018(3) 0.023(3) 0.001(2) 0.005(2) 0.002(2) N3 0.020(3) 0.024(3) 0.021(3) 0.001(2) 0.003(2) -0.005(2) N4 0.022(3) 0.022(3) 0.021(3) -0.002(2) 0.002(2) -0.002(2) O1 0.052(4) 0.045(4) 0.057(4) -0.012(3) 0.016(3) 0.006(3) O2 0.042(3) 0.051(4) 0.046(4) 0.016(3) 0.020(3) -0.003(3) O3 0.040(3) 0.042(3) 0.034(3) -0.004(3) -0.006(2) 0.001(2) C1 0.022(3) 0.021(3) 0.035(4) -0.004(3) 0.001(3) -0.002(3) C2 0.022(3) 0.027(4) 0.051(5) -0.007(3) -0.002(3) -0.007(3) C3 0.034(4) 0.035(4) 0.035(4) -0.005(4) -0.009(3) -0.004(3) C4 0.035(4) 0.033(4) 0.027(4) -0.001(3) -0.003(3) -0.003(3) C5 0.024(3) 0.017(3) 0.024(3) 0.003(3) 0.004(3) 0.001(2) C6 0.023(3) 0.020(3) 0.018(3) -0.003(3) 0.002(2) 0.001(2) C7 0.030(3) 0.028(4) 0.016(3) 0.000(3) 0.002(3) 0.001(3) C8 0.027(3) 0.028(4) 0.025(4) 0.000(3) 0.007(3) -0.006(3) C9 0.031(3) 0.023(3) 0.017(3) 0.004(3) 0.000(3) -0.002(3) C10 0.032(4) 0.035(4) 0.049(5) -0.003(4) 0.003(3) -0.002(3) C11 0.043(4) 0.037(5) 0.044(5) -0.006(4) 0.005(4) 0.007(4) C12 0.067(6) 0.030(5) 0.058(6) -0.017(4) 0.001(5) 0.005(4) C13 0.046(5) 0.058(7) 0.110(10) -0.041(7) -0.011(6) -0.011(5) C14 0.034(4) 0.041(5) 0.088(8) -0.028(5) 0.000(4) -0.008(4) C15 0.023(3) 0.024(4) 0.035(4) 0.017(3) -0.008(3) -0.006(3) C16 0.026(3) 0.027(4) 0.026(4) -0.001(3) 0.003(3) 0.003(3) C17 0.032(3) 0.020(3) 0.030(4) 0.001(3) 0.010(3) 0.002(3) _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 Re1 C17 1.916(7) . ? Re1 C16 1.922(7) . ? Re1 C15 1.974(8) . ? Re1 N2 2.127(5) . ? Re1 N1 2.196(5) . ? Re1 Cl1 2.4713(18) . ? N1 C1 1.342(8) . ? N1 C5 1.370(8) . ? N2 N3 1.316(7) . ? N2 C6 1.358(8) . ? N3 N4 1.341(7) . ? N4 C7 1.359(8) . ? N4 C8 1.468(8) . ? O1 C15 1.068(9) . ? O2 C16 1.152(8) . ? O3 C17 1.147(9) . ? C1 C2 1.378(10) . ? C1 H1A 0.9500 . ? C2 C3 1.375(11) . ? C2 H2A 0.9500 . ? C3 C4 1.386(10) . ? C3 H3A 0.9500 . ? C4 C5 1.387(9) . ? C4 H4A 0.9500 . ? C5 C6 1.464(9) . ? C6 C7 1.374(9) . ? C7 H7A 0.9500 . ? C8 C9 1.514(9) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C14 1.360(10) . ? C9 C10 1.381(10) . ? C10 C11 1.373(11) . ? C10 H10A 0.9500 . ? C11 C12 1.376(12) . ? C11 H11A 0.9500 . ? C12 C13 1.370(13) . ? C12 H12A 0.9500 . ? C13 C14 1.387(13) . ? C13 H13A 0.9500 . ? C14 H14A 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 C17 Re1 C16 91.6(3) . . ? C17 Re1 C15 88.9(3) . . ? C16 Re1 C15 91.6(3) . . ? C17 Re1 N2 96.5(2) . . ? C16 Re1 N2 170.6(2) . . ? C15 Re1 N2 93.3(2) . . ? C17 Re1 N1 170.5(2) . . ? C16 Re1 N1 97.1(2) . . ? C15 Re1 N1 94.5(2) . . ? N2 Re1 N1 74.5(2) . . ? C17 Re1 Cl1 91.9(2) . . ? C16 Re1 Cl1 93.4(2) . . ? C15 Re1 Cl1 174.9(2) . . ? N2 Re1 Cl1 81.59(15) . . ? N1 Re1 Cl1 83.90(14) . . ? C1 N1 C5 117.2(6) . . ? C1 N1 Re1 125.5(5) . . ? C5 N1 Re1 117.2(4) . . ? N3 N2 C6 110.9(5) . . ? N3 N2 Re1 130.2(4) . . ? C6 N2 Re1 118.2(4) . . ? N2 N3 N4 104.7(5) . . ? N3 N4 C7 113.3(5) . . ? N3 N4 C8 118.6(5) . . ? C7 N4 C8 127.9(6) . . ? N1 C1 C2 122.8(7) . . ? N1 C1 H1A 118.6 . . ? C2 C1 H1A 118.6 . . ? C3 C2 C1 119.8(6) . . ? C3 C2 H2A 120.1 . . ? C1 C2 H2A 120.1 . . ? C2 C3 C4 118.8(7) . . ? C2 C3 H3A 120.6 . . ? C4 C3 H3A 120.6 . . ? C3 C4 C5 118.8(7) . . ? C3 C4 H4A 120.6 . . ? C5 C4 H4A 120.6 . . ? N1 C5 C4 122.5(6) . . ? N1 C5 C6 113.3(6) . . ? C4 C5 C6 124.1(6) . . ? N2 C6 C7 108.1(5) . . ? N2 C6 C5 116.6(6) . . ? C7 C6 C5 135.2(6) . . ? N4 C7 C6 103.1(6) . . ? N4 C7 H7A 128.5 . . ? C6 C7 H7A 128.5 . . ? N4 C8 C9 111.6(5) . . ? N4 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? N4 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? C14 C9 C10 118.9(7) . . ? C14 C9 C8 118.1(7) . . ? C10 C9 C8 123.0(6) . . ? C11 C10 C9 121.4(7) . . ? C11 C10 H10A 119.3 . . ? C9 C10 H10A 119.3 . . ? C10 C11 C12 119.7(8) . . ? C10 C11 H11A 120.2 . . ? C12 C11 H11A 120.2 . . ? C13 C12 C11 118.8(8) . . ? C13 C12 H12A 120.6 . . ? C11 C12 H12A 120.6 . . ? C12 C13 C14 121.4(8) . . ? C12 C13 H13A 119.3 . . ? C14 C13 H13A 119.3 . . ? C9 C14 C13 119.7(8) . . ? C9 C14 H14A 120.1 . . ? C13 C14 H14A 120.1 . . ? O1 C15 Re1 175.0(7) . . ? O2 C16 Re1 178.0(7) . . ? O3 C17 Re1 176.9(6) . . ? 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 C17 Re1 N1 C1 -161.1(13) . . . . ? C16 Re1 N1 C1 -4.3(6) . . . . ? C15 Re1 N1 C1 87.9(5) . . . . ? N2 Re1 N1 C1 -179.9(6) . . . . ? Cl1 Re1 N1 C1 -97.0(5) . . . . ? C17 Re1 N1 C5 16.8(16) . . . . ? C16 Re1 N1 C5 173.5(5) . . . . ? C15 Re1 N1 C5 -94.3(5) . . . . ? N2 Re1 N1 C5 -2.1(4) . . . . ? Cl1 Re1 N1 C5 80.8(4) . . . . ? C17 Re1 N2 N3 -3.8(6) . . . . ? C16 Re1 N2 N3 145.8(14) . . . . ? C15 Re1 N2 N3 -93.1(6) . . . . ? N1 Re1 N2 N3 173.1(6) . . . . ? Cl1 Re1 N2 N3 87.2(5) . . . . ? C17 Re1 N2 C6 -173.2(5) . . . . ? C16 Re1 N2 C6 -23.6(18) . . . . ? C15 Re1 N2 C6 97.5(5) . . . . ? N1 Re1 N2 C6 3.7(4) . . . . ? Cl1 Re1 N2 C6 -82.3(4) . . . . ? C6 N2 N3 N4 -0.6(7) . . . . ? Re1 N2 N3 N4 -170.6(4) . . . . ? N2 N3 N4 C7 0.7(7) . . . . ? N2 N3 N4 C8 174.9(5) . . . . ? C5 N1 C1 C2 -0.1(10) . . . . ? Re1 N1 C1 C2 177.7(5) . . . . ? N1 C1 C2 C3 -0.6(11) . . . . ? C1 C2 C3 C4 0.3(12) . . . . ? C2 C3 C4 C5 0.6(12) . . . . ? C1 N1 C5 C4 1.1(9) . . . . ? Re1 N1 C5 C4 -176.9(5) . . . . ? C1 N1 C5 C6 178.4(6) . . . . ? Re1 N1 C5 C6 0.4(7) . . . . ? C3 C4 C5 N1 -1.3(11) . . . . ? C3 C4 C5 C6 -178.4(7) . . . . ? N3 N2 C6 C7 0.3(7) . . . . ? Re1 N2 C6 C7 171.6(4) . . . . ? N3 N2 C6 C5 -176.2(5) . . . . ? Re1 N2 C6 C5 -4.8(7) . . . . ? N1 C5 C6 N2 2.8(8) . . . . ? C4 C5 C6 N2 -179.9(6) . . . . ? N1 C5 C6 C7 -172.4(7) . . . . ? C4 C5 C6 C7 4.8(12) . . . . ? N3 N4 C7 C6 -0.5(7) . . . . ? C8 N4 C7 C6 -174.1(6) . . . . ? N2 C6 C7 N4 0.1(7) . . . . ? C5 C6 C7 N4 175.7(7) . . . . ? N3 N4 C8 C9 -73.0(7) . . . . ? C7 N4 C8 C9 100.2(8) . . . . ? N4 C8 C9 C14 150.5(8) . . . . ? N4 C8 C9 C10 -31.0(9) . . . . ? C14 C9 C10 C11 0.3(12) . . . . ? C8 C9 C10 C11 -178.2(7) . . . . ? C9 C10 C11 C12 -0.9(13) . . . . ? C10 C11 C12 C13 1.5(15) . . . . ? C11 C12 C13 C14 -1.5(18) . . . . ? C10 C9 C14 C13 -0.3(15) . . . . ? C8 C9 C14 C13 178.2(10) . . . . ? C12 C13 C14 C9 0.9(19) . . . . ? C17 Re1 C15 O1 20(7) . . . . ? C16 Re1 C15 O1 -72(7) . . . . ? N2 Re1 C15 O1 116(7) . . . . ? N1 Re1 C15 O1 -169(7) . . . . ? Cl1 Re1 C15 O1 119(7) . . . . ? C17 Re1 C16 O2 173(100) . . . . ? C15 Re1 C16 O2 -98(18) . . . . ? N2 Re1 C16 O2 23(19) . . . . ? N1 Re1 C16 O2 -3(18) . . . . ? Cl1 Re1 C16 O2 81(18) . . . . ? C16 Re1 C17 O3 -162(12) . . . . ? C15 Re1 C17 O3 107(12) . . . . ? N2 Re1 C17 O3 14(12) . . . . ? N1 Re1 C17 O3 -5(13) . . . . ? Cl1 Re1 C17 O3 -68(12) . . . . ? #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== # Attachment 'Glcpyta_rev.cif' #============================================================================== data___Glcpyta _database_code_depnum_ccdc_archive 'CCDC 669575' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C15 H20 N4 O6 ' _chemical_formula_moiety 'C15 H20 N4 O6 ' _chemical_formula_weight 352.35 _chemical_melting_point ? _chemical_absolute_configuration syn #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,-Z #------------------------------------------------------------------------------ _cell_length_a 11.560(4) _cell_length_b 5.4449(17) _cell_length_c 13.267(5) _cell_angle_alpha 90.0000 _cell_angle_beta 100.247(4) _cell_angle_gamma 90.0000 _cell_volume 821.8(5) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2604 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 173.1 #------------------------------------------------------------------------------ _exptl_crystal_description chip _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372.00 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Higashi, T. (1999). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.962 _exptl_absorpt_correction_T_max 0.978 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_reflns_number 6404 _diffrn_reflns_av_R_equivalents 0.025 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2063 _reflns_number_gt 1765 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.0506 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 2063 _refine_ls_number_parameters 246 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.0007Fo^2^ + 1.0000\s(Fo^2^)]' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.20 _refine_diff_density_min -0.21 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 O(1) O 0.68086(15) 0.1966(3) 0.77151(12) 0.0254(4) Uani 1.00 1 d . . . O(2) O 0.70998(14) 0.3230(3) 0.93799(13) 0.0244(4) Uani 1.00 1 d . . . O(3) O 0.58564(16) -0.0968(3) 0.99244(13) 0.0292(4) Uani 1.00 1 d . . . O(4) O 0.43118(14) -0.3030(4) 0.82722(13) 0.0304(4) Uani 1.00 1 d . . . O(5) O 0.51994(16) -0.3248(4) 0.63957(13) 0.0329(5) Uani 1.00 1 d . . . O(6) O 0.58550(18) 0.2561(4) 0.55643(14) 0.0391(5) Uani 1.00 1 d . . . N(1) N 0.7693(2) -0.0662(5) 1.31464(17) 0.0356(6) Uani 1.00 1 d . . . N(2) N 1.01400(18) 0.2114(5) 1.21483(17) 0.0344(6) Uani 1.00 1 d . . . N(3) N 1.00667(18) 0.3872(5) 1.14529(17) 0.0328(6) Uani 1.00 1 d . . . N(4) N 0.89105(18) 0.4373(4) 1.11579(16) 0.0282(5) Uani 1.00 1 d . . . C(1) C 0.7485(3) -0.2479(6) 1.3770(2) 0.0438(9) Uani 1.00 1 d . . . C(2) C 0.8311(3) -0.4124(7) 1.4232(2) 0.0507(9) Uani 1.00 1 d . . . C(3) C 0.9450(3) -0.3922(7) 1.4044(2) 0.0504(10) Uani 1.00 1 d . . . C(4) C 0.9700(2) -0.2049(6) 1.3409(2) 0.0398(8) Uani 1.00 1 d . . . C(5) C 0.8808(2) -0.0473(6) 1.29752(19) 0.0297(6) Uani 1.00 1 d . . . C(6) C 0.9032(2) 0.1497(5) 1.22816(19) 0.0276(6) Uani 1.00 1 d . . . C(7) C 0.8251(2) 0.2943(5) 1.1649(2) 0.0297(6) Uani 1.00 1 d . . . C(8) C 0.8514(2) 0.5978(5) 1.02827(19) 0.0287(6) Uani 1.00 1 d . . . C(9) C 0.8182(2) 0.4470(6) 0.93152(19) 0.0282(6) Uani 1.00 1 d . . . C(10) C 0.6894(2) 0.1173(5) 0.87531(18) 0.0215(5) Uani 1.00 1 d . . . C(11) C 0.5750(2) -0.0007(5) 0.89142(18) 0.0221(5) Uani 1.00 1 d . . . C(12) C 0.5438(2) -0.2106(5) 0.81558(18) 0.0228(6) Uani 1.00 1 d . . . C(13) C 0.5448(2) -0.1218(5) 0.70761(18) 0.0240(6) Uani 1.00 1 d . . . C(14) C 0.6642(2) -0.0070(5) 0.70241(18) 0.0253(6) Uani 1.00 1 d . . . C(15) C 0.6765(2) 0.0893(6) 0.5984(2) 0.0340(7) Uani 1.00 1 d . . . H(1) H 0.6730 -0.2856 1.3865 0.053 Uiso 1.00 1 c R . . H(2) H 0.8207 -0.5600 1.4747 0.061 Uiso 1.00 1 c R . . H(3) H 1.0144 -0.4891 1.4357 0.060 Uiso 1.00 1 c R . . H(4) H 1.0493 -0.1891 1.3173 0.047 Uiso 1.00 1 c R . . H(5) H 0.7417 0.3251 1.1548 0.036 Uiso 1.00 1 c R . . H(6) H 0.7757 0.6843 1.0414 0.034 Uiso 1.00 1 c R . . H(7) H 0.9227 0.6963 1.0204 0.034 Uiso 1.00 1 c R . . H(8) H 0.8029 0.5635 0.8702 0.033 Uiso 1.00 1 c R . . H(9) H 0.8749 0.3185 0.9282 0.033 Uiso 1.00 1 c R . . H(10) H 0.7585 -0.0006 0.8907 0.026 Uiso 1.00 1 c R . . H(11) H 0.5172 0.1258 0.8819 0.027 Uiso 1.00 1 c R . . H(12) H 0.6078 -0.3341 0.8357 0.027 Uiso 1.00 1 c R . . H(13) H 0.4829 -0.0051 0.6862 0.029 Uiso 1.00 1 c R . . H(14) H 0.7269 -0.1402 0.7239 0.030 Uiso 1.00 1 c R . . H(15) H 0.6714 -0.0570 0.5491 0.041 Uiso 1.00 1 c R . . H(16) H 0.7634 0.1850 0.5971 0.041 Uiso 1.00 1 c R . . H(17) H 0.5826 0.0556 1.0390 0.036 Uiso 1.00 1 c R . . H(18) H 0.4006 -0.3805 0.7715 0.037 Uiso 1.00 1 c R . . H(19) H 0.4770 -0.2987 0.5922 0.039 Uiso 1.00 1 c R . . H(20) H 0.5831 0.3771 0.5963 0.046 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0315(8) 0.0261(9) 0.0191(8) -0.0016(8) 0.0055(6) 0.0016(8) O(2) 0.0224(8) 0.0265(10) 0.0243(8) -0.0030(8) 0.0037(6) -0.0025(8) O(3) 0.0395(9) 0.0297(11) 0.0194(8) -0.0038(9) 0.0084(7) 0.0002(8) O(4) 0.0255(8) 0.0366(11) 0.0294(9) -0.0078(9) 0.0053(6) -0.0061(9) O(5) 0.0436(10) 0.0304(11) 0.0217(8) 0.0023(10) -0.0027(7) -0.0043(8) O(6) 0.0616(12) 0.0318(12) 0.0210(9) 0.0070(11) -0.0010(8) 0.0002(8) N(1) 0.0408(12) 0.0403(15) 0.0265(11) -0.0081(12) 0.0079(9) -0.0033(12) N(2) 0.0276(10) 0.0442(15) 0.0316(12) 0.0053(12) 0.0055(8) 0.0032(12) N(3) 0.0227(10) 0.0436(16) 0.0315(11) 0.0011(11) 0.0034(8) 0.0034(12) N(4) 0.0240(9) 0.0348(13) 0.0244(10) -0.0011(10) 0.0006(7) 0.0006(10) C(1) 0.0571(18) 0.044(2) 0.0319(15) -0.0191(17) 0.0126(13) -0.0057(15) C(2) 0.082(2) 0.0378(19) 0.0321(16) -0.0153(19) 0.0090(15) 0.0020(16) C(3) 0.073(2) 0.039(2) 0.0369(16) 0.0035(19) 0.0026(15) 0.0049(16) C(4) 0.0505(17) 0.0371(17) 0.0309(14) 0.0066(15) 0.0048(12) 0.0006(14) C(5) 0.0352(13) 0.0325(15) 0.0211(11) -0.0029(13) 0.0036(9) -0.0027(11) C(6) 0.0267(12) 0.0321(16) 0.0241(12) 0.0022(11) 0.0043(9) -0.0027(12) C(7) 0.0222(11) 0.0380(16) 0.0286(12) -0.0018(12) 0.0034(9) 0.0025(13) C(8) 0.0259(11) 0.0305(15) 0.0283(12) -0.0040(12) 0.0013(9) 0.0009(12) C(9) 0.0226(11) 0.0322(15) 0.0285(12) -0.0025(12) 0.0009(9) 0.0021(12) C(10) 0.0237(11) 0.0214(13) 0.0191(10) 0.0011(10) 0.0030(8) 0.0009(10) C(11) 0.0237(10) 0.0212(13) 0.0220(11) 0.0023(10) 0.0054(8) 0.0014(10) C(12) 0.0199(10) 0.0265(14) 0.0217(11) 0.0007(10) 0.0032(8) -0.0024(11) C(13) 0.0273(11) 0.0222(14) 0.0215(11) 0.0040(11) 0.0019(9) -0.0010(11) C(14) 0.0282(11) 0.0276(15) 0.0202(11) 0.0049(12) 0.0045(9) -0.0002(11) C(15) 0.0428(15) 0.0384(17) 0.0217(12) 0.0032(14) 0.0083(10) 0.0020(13) #============================================================================== _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution SIR92 _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O(1) C(10) 1.430(2) yes . . O(1) C(14) 1.429(3) yes . . O(2) C(9) 1.438(3) yes . . O(2) C(10) 1.390(3) yes . . O(3) C(11) 1.424(3) yes . . O(4) C(12) 1.430(3) yes . . O(5) C(13) 1.423(3) yes . . O(6) C(15) 1.426(3) yes . . N(1) C(1) 1.339(4) yes . . N(1) C(5) 1.352(3) yes . . N(2) N(3) 1.322(3) yes . . N(2) C(6) 1.366(3) yes . . N(3) N(4) 1.352(2) yes . . N(4) C(7) 1.337(3) yes . . N(4) C(8) 1.460(3) yes . . C(1) C(2) 1.372(4) yes . . C(2) C(3) 1.388(5) yes . . C(3) C(4) 1.385(5) yes . . C(4) C(5) 1.386(4) yes . . C(5) C(6) 1.466(4) yes . . C(6) C(7) 1.367(3) yes . . C(8) C(9) 1.515(3) yes . . C(10) C(11) 1.518(3) yes . . C(11) C(12) 1.523(3) yes . . C(12) C(13) 1.514(3) yes . . C(13) C(14) 1.529(3) yes . . C(14) C(15) 1.507(3) yes . . O(3) H(17) 1.038 no . . O(4) H(18) 0.870 no . . O(5) H(19) 0.742 no . . O(6) H(20) 0.848 no . . C(1) H(1) 0.927 no . . C(2) H(2) 1.076 no . . C(3) H(3) 0.987 no . . C(4) H(4) 1.024 no . . C(7) H(5) 0.964 no . . C(8) H(6) 1.035 no . . C(8) H(7) 1.004 no . . C(9) H(8) 1.022 no . . C(9) H(9) 0.965 no . . C(10) H(10) 1.017 no . . C(11) H(11) 0.952 no . . C(12) H(12) 1.000 no . . C(13) H(13) 0.961 no . . C(14) H(14) 1.029 no . . C(15) H(15) 1.026 no . . C(15) H(16) 1.134 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(10) O(1) C(14) 111.2(2) yes . . . C(9) O(2) C(10) 113.64(19) yes . . . C(1) N(1) C(5) 116.2(2) yes . . . N(3) N(2) C(6) 108.9(2) yes . . . N(2) N(3) N(4) 106.6(2) yes . . . N(3) N(4) C(7) 111.2(2) yes . . . N(3) N(4) C(8) 120.3(2) yes . . . C(7) N(4) C(8) 127.6(2) yes . . . N(1) C(1) C(2) 124.8(3) yes . . . C(1) C(2) C(3) 118.4(3) yes . . . C(2) C(3) C(4) 118.3(3) yes . . . C(3) C(4) C(5) 119.2(3) yes . . . N(1) C(5) C(4) 123.0(2) yes . . . N(1) C(5) C(6) 116.2(2) yes . . . C(4) C(5) C(6) 120.8(2) yes . . . N(2) C(6) C(5) 122.4(2) yes . . . N(2) C(6) C(7) 108.1(2) yes . . . C(5) C(6) C(7) 129.5(2) yes . . . N(4) C(7) C(6) 105.3(2) yes . . . N(4) C(8) C(9) 110.2(2) yes . . . O(2) C(9) C(8) 107.2(2) yes . . . O(1) C(10) O(2) 107.9(2) yes . . . O(1) C(10) C(11) 110.55(17) yes . . . O(2) C(10) C(11) 108.5(2) yes . . . O(3) C(11) C(10) 110.90(18) yes . . . O(3) C(11) C(12) 108.5(2) yes . . . C(10) C(11) C(12) 109.5(2) yes . . . O(4) C(12) C(11) 107.8(2) yes . . . O(4) C(12) C(13) 111.99(17) yes . . . C(11) C(12) C(13) 110.2(2) yes . . . O(5) C(13) C(12) 108.5(2) yes . . . O(5) C(13) C(14) 111.8(2) yes . . . C(12) C(13) C(14) 109.38(18) yes . . . O(1) C(14) C(13) 107.9(2) yes . . . O(1) C(14) C(15) 107.1(2) yes . . . C(13) C(14) C(15) 114.62(19) yes . . . O(6) C(15) C(14) 113.4(2) yes . . . C(11) O(3) H(17) 105.1 no . . . C(12) O(4) H(18) 108.6 no . . . C(13) O(5) H(19) 114.7 no . . . C(15) O(6) H(20) 110.8 no . . . N(1) C(1) H(1) 121.7 no . . . C(2) C(1) H(1) 113.1 no . . . C(1) C(2) H(2) 128.6 no . . . C(3) C(2) H(2) 113.0 no . . . C(2) C(3) H(3) 127.4 no . . . C(4) C(3) H(3) 114.1 no . . . C(3) C(4) H(4) 122.9 no . . . C(5) C(4) H(4) 117.5 no . . . N(4) C(7) H(5) 118.2 no . . . C(6) C(7) H(5) 136.1 no . . . N(4) C(8) H(6) 107.0 no . . . N(4) C(8) H(7) 104.8 no . . . C(9) C(8) H(6) 107.2 no . . . C(9) C(8) H(7) 106.9 no . . . H(6) C(8) H(7) 120.6 no . . . O(2) C(9) H(8) 108.0 no . . . O(2) C(9) H(9) 105.5 no . . . C(8) C(9) H(8) 108.6 no . . . C(8) C(9) H(9) 111.1 no . . . H(8) C(9) H(9) 115.9 no . . . O(1) C(10) H(10) 107.5 no . . . O(2) C(10) H(10) 110.1 no . . . C(11) C(10) H(10) 112.2 no . . . O(3) C(11) H(11) 109.3 no . . . C(10) C(11) H(11) 106.4 no . . . C(12) C(11) H(11) 112.2 no . . . O(4) C(12) H(12) 112.3 no . . . C(11) C(12) H(12) 104.5 no . . . C(13) C(12) H(12) 109.8 no . . . O(5) C(13) H(13) 105.7 no . . . C(12) C(13) H(13) 111.1 no . . . C(14) C(13) H(13) 110.3 no . . . O(1) C(14) H(14) 111.1 no . . . C(13) C(14) H(14) 107.3 no . . . C(15) C(14) H(14) 108.9 no . . . O(6) C(15) H(15) 106.9 no . . . O(6) C(15) H(16) 107.2 no . . . C(14) C(15) H(15) 108.0 no . . . C(14) C(15) H(16) 113.7 no . . . H(15) C(15) H(16) 107.3 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C(10) O(1) C(14) C(13) 65.3(2) ? . . . . C(10) O(1) C(14) C(15) -170.81(19) ? . . . . C(14) O(1) C(10) O(2) 177.69(17) ? . . . . C(14) O(1) C(10) C(11) -63.7(2) ? . . . . C(9) O(2) C(10) O(1) -61.8(2) ? . . . . C(9) O(2) C(10) C(11) 178.32(19) ? . . . . C(10) O(2) C(9) C(8) -158.8(2) ? . . . . C(1) N(1) C(5) C(4) 0.1(3) ? . . . . C(1) N(1) C(5) C(6) 179.2(2) ? . . . . C(5) N(1) C(1) C(2) -0.2(4) ? . . . . N(3) N(2) C(6) C(5) 177.5(2) ? . . . . N(3) N(2) C(6) C(7) -0.4(3) ? . . . . C(6) N(2) N(3) N(4) 0.6(3) ? . . . . N(2) N(3) N(4) C(7) -0.6(3) ? . . . . N(2) N(3) N(4) C(8) -170.7(2) ? . . . . N(3) N(4) C(7) C(6) 0.3(3) ? . . . . N(3) N(4) C(8) C(9) 93.5(2) ? . . . . C(7) N(4) C(8) C(9) -74.9(3) ? . . . . C(8) N(4) C(7) C(6) 169.6(2) ? . . . . N(1) C(1) C(2) C(3) -0.3(5) ? . . . . C(1) C(2) C(3) C(4) 0.8(4) ? . . . . C(2) C(3) C(4) C(5) -0.9(4) ? . . . . C(3) C(4) C(5) N(1) 0.4(4) ? . . . . C(3) C(4) C(5) C(6) -178.6(2) ? . . . . N(1) C(5) C(6) N(2) 170.9(2) ? . . . . N(1) C(5) C(6) C(7) -11.6(4) ? . . . . C(4) C(5) C(6) N(2) -10.0(4) ? . . . . C(4) C(5) C(6) C(7) 167.5(3) ? . . . . N(2) C(6) C(7) N(4) 0.1(2) ? . . . . C(5) C(6) C(7) N(4) -177.7(2) ? . . . . N(4) C(8) C(9) O(2) 72.0(2) ? . . . . O(1) C(10) C(11) O(3) 175.6(2) ? . . . . O(1) C(10) C(11) C(12) 55.9(2) ? . . . . O(2) C(10) C(11) O(3) -66.2(2) ? . . . . O(2) C(10) C(11) C(12) 174.11(18) ? . . . . O(3) C(11) C(12) O(4) 63.7(2) ? . . . . O(3) C(11) C(12) C(13) -173.84(19) ? . . . . C(10) C(11) C(12) O(4) -175.13(19) ? . . . . C(10) C(11) C(12) C(13) -52.7(2) ? . . . . O(4) C(12) C(13) O(5) -62.3(2) ? . . . . O(4) C(12) C(13) C(14) 175.5(2) ? . . . . C(11) C(12) C(13) O(5) 177.69(19) ? . . . . C(11) C(12) C(13) C(14) 55.5(2) ? . . . . O(5) C(13) C(14) O(1) 179.06(18) ? . . . . O(5) C(13) C(14) C(15) 59.9(3) ? . . . . C(12) C(13) C(14) O(1) -60.8(2) ? . . . . C(12) C(13) C(14) C(15) -179.96(19) ? . . . . O(1) C(14) C(15) O(6) -66.2(2) ? . . . . C(13) C(14) C(15) O(6) 53.5(3) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O(1) O(2) 2.281(2) ? . . O(1) O(5) 3.487(2) ? . 1_565 O(1) O(6) 2.889(2) ? . . O(1) C(9) 2.773(3) ? . . O(1) C(11) 2.424(3) ? . . O(1) C(12) 2.845(3) ? . . O(1) C(13) 2.393(3) ? . . O(1) C(15) 2.362(3) ? . . O(2) O(1) 2.281(2) ? . . O(2) O(3) 2.860(2) ? . . O(2) O(3) 3.597(2) ? . 1_565 O(2) N(4) 2.929(2) ? . . O(2) C(7) 3.072(2) ? . . O(2) C(8) 2.377(3) ? . . O(2) C(11) 2.362(3) ? . . O(2) C(12) 3.415(3) ? . 1_565 O(2) C(14) 3.562(3) ? . . O(3) O(2) 3.597(2) ? . 1_545 O(3) O(2) 2.860(2) ? . . O(3) O(3) 3.393(2) ? . 2_647 O(3) O(3) 3.393(2) ? . 2_657 O(3) O(4) 2.804(2) ? . . O(3) O(4) 2.913(2) ? . 2_657 O(3) C(8) 3.451(3) ? . 1_545 O(3) C(10) 2.424(3) ? . . O(3) C(11) 3.418(3) ? . 2_647 O(3) C(12) 2.392(2) ? . . O(4) O(3) 2.804(2) ? . . O(4) O(3) 2.913(2) ? . 2_647 O(4) O(5) 2.859(2) ? . . O(4) N(1) 3.068(2) ? . 2_647 O(4) C(7) 3.030(3) ? . 2_647 O(4) C(11) 2.386(3) ? . . O(4) C(13) 2.441(3) ? . . O(5) O(1) 3.487(2) ? . 1_545 O(5) O(4) 2.859(2) ? . . O(5) O(6) 2.701(3) ? . 1_545 O(5) O(6) 3.477(3) ? . . O(5) O(6) 2.704(2) ? . 2_646 O(5) C(12) 2.385(2) ? . . O(5) C(14) 2.445(3) ? . . O(5) C(15) 3.001(3) ? . . O(5) C(15) 3.576(2) ? . 2_646 O(6) O(1) 2.889(2) ? . . O(6) O(5) 3.477(3) ? . . O(6) O(5) 2.701(3) ? . 1_565 O(6) O(5) 2.704(2) ? . 2_656 O(6) O(6) 3.537(2) ? . 2_646 O(6) O(6) 3.537(2) ? . 2_656 O(6) C(13) 2.969(3) ? . . O(6) C(14) 2.450(3) ? . . N(1) O(4) 3.068(2) ? . 2_657 N(1) C(2) 2.402(4) ? . . N(1) C(3) 2.799(4) ? . . N(1) C(4) 2.406(4) ? . . N(1) C(6) 2.393(3) ? . . N(1) C(7) 2.945(4) ? . . N(2) N(4) 2.144(3) ? . . N(2) C(3) 3.512(4) ? . 1_565 N(2) C(4) 2.915(4) ? . . N(2) C(5) 2.482(3) ? . . N(2) C(7) 2.212(3) ? . . N(2) C(8) 3.526(3) ? . . N(2) C(9) 3.308(3) ? . 2_747 N(3) C(4) 3.498(4) ? . 1_565 N(3) C(5) 3.583(3) ? . . N(3) C(6) 2.186(3) ? . . N(3) C(7) 2.219(3) ? . . N(3) C(8) 2.440(3) ? . . N(3) C(8) 3.438(3) ? . 2_747 N(3) C(9) 3.271(3) ? . . N(3) C(9) 3.408(3) ? . 2_747 N(4) O(2) 2.929(2) ? . . N(4) N(2) 2.144(3) ? . . N(4) C(4) 3.546(3) ? . 1_565 N(4) C(5) 3.590(3) ? . . N(4) C(6) 2.149(3) ? . . N(4) C(9) 2.440(3) ? . . C(1) C(3) 2.370(5) ? . . C(1) C(4) 2.698(4) ? . . C(1) C(5) 2.285(4) ? . . C(2) N(1) 2.402(4) ? . . C(2) C(4) 2.381(5) ? . . C(2) C(5) 2.721(4) ? . . C(3) N(1) 2.799(4) ? . . C(3) N(2) 3.512(4) ? . 1_545 C(3) C(1) 2.370(5) ? . . C(3) C(5) 2.390(4) ? . . C(3) C(6) 3.394(4) ? . 1_545 C(4) N(1) 2.406(4) ? . . C(4) N(2) 2.915(4) ? . . C(4) N(3) 3.498(4) ? . 1_545 C(4) N(4) 3.546(3) ? . 1_545 C(4) C(1) 2.698(4) ? . . C(4) C(2) 2.381(5) ? . . C(4) C(6) 2.480(4) ? . . C(5) N(2) 2.482(3) ? . . C(5) N(3) 3.583(3) ? . . C(5) N(4) 3.590(3) ? . . C(5) C(1) 2.285(4) ? . . C(5) C(2) 2.721(4) ? . . C(5) C(3) 2.390(4) ? . . C(5) C(7) 2.562(4) ? . . C(6) N(1) 2.393(3) ? . . C(6) N(3) 2.186(3) ? . . C(6) N(4) 2.149(3) ? . . C(6) C(3) 3.394(4) ? . 1_565 C(6) C(4) 2.480(4) ? . . C(6) C(8) 3.575(3) ? . . C(7) O(2) 3.072(2) ? . . C(7) O(4) 3.030(3) ? . 2_657 C(7) N(1) 2.945(4) ? . . C(7) N(2) 2.212(3) ? . . C(7) N(3) 2.219(3) ? . . C(7) C(5) 2.562(4) ? . . C(7) C(8) 2.512(4) ? . . C(7) C(9) 3.194(3) ? . . C(8) O(2) 2.377(3) ? . . C(8) O(3) 3.451(3) ? . 1_565 C(8) N(2) 3.526(3) ? . . C(8) N(3) 2.440(3) ? . . C(8) N(3) 3.438(3) ? . 2_757 C(8) C(6) 3.575(3) ? . . C(8) C(7) 2.512(4) ? . . C(9) O(1) 2.773(3) ? . . C(9) N(2) 3.308(3) ? . 2_757 C(9) N(3) 3.271(3) ? . . C(9) N(3) 3.408(3) ? . 2_757 C(9) N(4) 2.440(3) ? . . C(9) C(7) 3.194(3) ? . . C(9) C(10) 2.367(3) ? . . C(10) O(3) 2.424(3) ? . . C(10) C(9) 2.367(3) ? . . C(10) C(12) 2.484(3) ? . . C(10) C(13) 2.849(3) ? . . C(10) C(14) 2.360(3) ? . . C(11) O(1) 2.424(3) ? . . C(11) O(2) 2.362(3) ? . . C(11) O(3) 3.418(3) ? . 2_657 C(11) O(4) 2.386(3) ? . . C(11) C(13) 2.490(3) ? . . C(11) C(14) 2.876(3) ? . . C(12) O(1) 2.845(3) ? . . C(12) O(2) 3.415(3) ? . 1_545 C(12) O(3) 2.392(2) ? . . C(12) O(5) 2.385(2) ? . . C(12) C(10) 2.484(3) ? . . C(12) C(14) 2.483(3) ? . . C(13) O(1) 2.393(3) ? . . C(13) O(4) 2.441(3) ? . . C(13) O(6) 2.969(3) ? . . C(13) C(10) 2.849(3) ? . . C(13) C(11) 2.490(3) ? . . C(13) C(15) 2.554(4) ? . . C(14) O(2) 3.562(3) ? . . C(14) O(5) 2.445(3) ? . . C(14) O(6) 2.450(3) ? . . C(14) C(10) 2.360(3) ? . . C(14) C(11) 2.876(3) ? . . C(14) C(12) 2.483(3) ? . . C(15) O(1) 2.362(3) ? . . C(15) O(5) 3.001(3) ? . . C(15) O(5) 3.576(2) ? . 2_656 C(15) C(13) 2.554(4) ? . . O(1) H(4) 3.580 ? . 2_757 O(1) H(8) 2.653 ? . . O(1) H(9) 2.852 ? . . O(1) H(10) 1.988 ? . . O(1) H(11) 2.619 ? . . O(1) H(12) 3.169 ? . . O(1) H(12) 2.868 ? . 1_565 O(1) H(13) 2.608 ? . . O(1) H(14) 2.040 ? . . O(1) H(15) 3.242 ? . . O(1) H(16) 2.656 ? . . O(1) H(20) 2.591 ? . . O(2) H(5) 2.834 ? . . O(2) H(6) 2.441 ? . . O(2) H(7) 3.228 ? . . O(2) H(8) 2.005 ? . . O(2) H(9) 1.934 ? . . O(2) H(10) 1.984 ? . . O(2) H(11) 2.466 ? . . O(2) H(12) 2.480 ? . 1_565 O(2) H(17) 2.605 ? . . O(3) H(5) 3.434 ? . . O(3) H(6) 2.483 ? . 1_545 O(3) H(10) 2.655 ? . . O(3) H(11) 1.957 ? . . O(3) H(11) 2.679 ? . 2_647 O(3) H(12) 2.499 ? . . O(3) H(17) 2.693 ? . 2_647 O(3) H(18) 3.323 ? . 2_657 O(4) H(5) 2.170 ? . 2_647 O(4) H(11) 3.307 ? . 1_545 O(4) H(11) 2.590 ? . . O(4) H(12) 2.032 ? . . O(4) H(13) 2.624 ? . . O(4) H(17) 1.968 ? . 2_647 O(4) H(19) 3.254 ? . . O(5) H(1) 3.334 ? . 2_647 O(5) H(12) 2.621 ? . . O(5) H(13) 1.921 ? . . O(5) H(14) 2.652 ? . . O(5) H(15) 2.716 ? . . O(5) H(15) 3.284 ? . 2_646 O(5) H(18) 2.433 ? . . O(5) H(20) 1.910 ? . 1_545 O(5) H(20) 3.330 ? . 2_646 O(6) H(1) 3.218 ? . 2_657 O(6) H(2) 3.259 ? . 1_564 O(6) H(13) 2.669 ? . . O(6) H(13) 3.431 ? . 2_656 O(6) H(14) 3.313 ? . . O(6) H(15) 1.984 ? . . O(6) H(15) 3.215 ? . 2_656 O(6) H(16) 2.068 ? . . O(6) H(19) 3.337 ? . . O(6) H(19) 2.808 ? . 1_565 O(6) H(19) 1.998 ? . 2_656 O(6) H(20) 3.280 ? . 2_646 N(1) H(1) 1.988 ? . . N(1) H(2) 3.412 ? . . N(1) H(2) 3.465 ? . 1_565 N(1) H(4) 3.300 ? . . N(1) H(5) 2.983 ? . . N(1) H(15) 3.495 ? . 1_556 N(1) H(18) 2.321 ? . 2_657 N(2) H(3) 3.353 ? . 1_565 N(2) H(4) 2.563 ? . . N(2) H(4) 3.532 ? . 1_565 N(2) H(5) 3.168 ? . . N(2) H(7) 3.331 ? . 2_747 N(2) H(8) 2.692 ? . 2_747 N(2) H(9) 3.270 ? . 2_747 N(2) H(10) 3.556 ? . 2_757 N(2) H(14) 3.069 ? . 2_757 N(3) H(4) 3.221 ? . 1_565 N(3) H(5) 3.106 ? . . N(3) H(6) 3.215 ? . . N(3) H(7) 2.439 ? . . N(3) H(7) 2.687 ? . 2_747 N(3) H(8) 2.856 ? . 2_747 N(3) H(9) 3.032 ? . . N(3) H(9) 3.590 ? . 2_747 N(3) H(9) 2.969 ? . 2_757 N(3) H(10) 2.904 ? . 2_757 N(3) H(14) 3.258 ? . 2_757 N(4) H(4) 3.591 ? . 1_565 N(4) H(5) 1.985 ? . . N(4) H(6) 2.023 ? . . N(4) H(7) 1.972 ? . . N(4) H(7) 3.318 ? . 2_747 N(4) H(8) 3.308 ? . . N(4) H(9) 2.546 ? . . N(4) H(9) 3.540 ? . 2_757 C(1) H(2) 2.209 ? . . C(1) H(3) 3.306 ? . . C(1) H(13) 3.003 ? . 2_647 C(1) H(15) 2.795 ? . 1_556 C(1) H(18) 3.106 ? . 2_657 C(2) H(1) 1.933 ? . . C(2) H(3) 2.137 ? . . C(2) H(3) 3.290 ? . 2_758 C(2) H(4) 3.328 ? . . C(2) H(15) 3.323 ? . 1_556 C(2) H(16) 3.375 ? . 1_546 C(3) H(1) 3.165 ? . . C(3) H(2) 2.061 ? . . C(3) H(2) 3.411 ? . 2_758 C(3) H(3) 3.031 ? . 2_758 C(3) H(4) 2.123 ? . . C(3) H(16) 3.401 ? . 2_747 C(4) H(2) 3.310 ? . . C(4) H(2) 3.219 ? . 2_758 C(4) H(3) 2.002 ? . . C(4) H(3) 3.164 ? . 2_758 C(4) H(16) 3.104 ? . 2_747 C(5) H(1) 3.140 ? . . C(5) H(3) 3.244 ? . . C(5) H(3) 3.546 ? . 2_758 C(5) H(4) 2.068 ? . . C(5) H(5) 3.033 ? . . C(5) H(18) 3.345 ? . 2_657 C(6) H(3) 3.441 ? . 1_565 C(6) H(4) 2.635 ? . . C(6) H(5) 2.167 ? . . C(6) H(18) 3.517 ? . 2_657 C(7) H(6) 2.681 ? . . C(7) H(7) 3.242 ? . . C(7) H(9) 3.295 ? . . C(7) H(17) 3.268 ? . . C(7) H(18) 3.035 ? . 2_657 C(8) H(5) 2.718 ? . . C(8) H(7) 3.552 ? . 2_747 C(8) H(8) 2.081 ? . . C(8) H(9) 2.069 ? . . C(8) H(9) 3.337 ? . 2_757 C(8) H(10) 2.927 ? . 1_565 C(8) H(12) 3.469 ? . 1_565 C(9) H(5) 3.306 ? . . C(9) H(6) 2.072 ? . . C(9) H(7) 2.046 ? . . C(9) H(7) 3.249 ? . 2_747 C(9) H(10) 2.564 ? . . C(9) H(10) 3.112 ? . 1_565 C(9) H(12) 2.803 ? . 1_565 C(9) H(14) 3.566 ? . 1_565 C(10) H(6) 3.260 ? . 1_545 C(10) H(8) 3.295 ? . 1_545 C(10) H(8) 2.768 ? . . C(10) H(9) 2.400 ? . . C(10) H(11) 2.008 ? . . C(10) H(12) 2.651 ? . . C(10) H(12) 3.148 ? . 1_565 C(10) H(13) 3.210 ? . . C(10) H(14) 2.549 ? . . C(10) H(17) 2.702 ? . . C(11) H(6) 3.262 ? . 1_545 C(11) H(8) 3.594 ? . 1_545 C(11) H(10) 2.123 ? . . C(11) H(12) 2.021 ? . . C(11) H(13) 2.742 ? . . C(11) H(14) 3.160 ? . . C(11) H(17) 1.968 ? . . C(11) H(17) 3.257 ? . 2_647 C(11) H(18) 3.120 ? . . C(12) H(5) 3.399 ? . 2_647 C(12) H(8) 3.200 ? . 1_545 C(12) H(10) 2.753 ? . . C(12) H(11) 2.079 ? . . C(12) H(13) 2.065 ? . . C(12) H(14) 2.649 ? . . C(12) H(17) 3.258 ? . . C(12) H(17) 2.913 ? . 2_647 C(12) H(18) 1.896 ? . . C(12) H(19) 2.965 ? . . C(13) H(1) 3.183 ? . 2_657 C(13) H(10) 3.210 ? . . C(13) H(11) 2.744 ? . . C(13) H(12) 2.077 ? . . C(13) H(14) 2.081 ? . . C(13) H(15) 2.790 ? . . C(13) H(16) 3.556 ? . . C(13) H(18) 2.446 ? . . C(13) H(19) 1.860 ? . . C(13) H(20) 3.171 ? . 1_545 C(13) H(20) 3.161 ? . . C(14) H(8) 3.424 ? . 1_545 C(14) H(10) 2.542 ? . . C(14) H(11) 3.244 ? . . C(14) H(12) 2.671 ? . . C(14) H(13) 2.069 ? . . C(14) H(15) 2.068 ? . . C(14) H(16) 2.220 ? . . C(14) H(19) 2.867 ? . . C(14) H(20) 2.601 ? . . C(15) H(1) 3.468 ? . 1_554 C(15) H(2) 3.177 ? . 1_564 C(15) H(4) 3.391 ? . 2_757 C(15) H(13) 2.749 ? . . C(15) H(14) 2.081 ? . . C(15) H(19) 3.118 ? . . C(15) H(19) 2.884 ? . 2_656 C(15) H(20) 1.900 ? . . H(1) O(5) 3.334 ? . 2_657 H(1) O(6) 3.218 ? . 2_647 H(1) N(1) 1.988 ? . . H(1) C(2) 1.933 ? . . H(1) C(3) 3.165 ? . . H(1) C(5) 3.140 ? . . H(1) C(13) 3.183 ? . 2_647 H(1) C(15) 3.468 ? . 1_556 H(1) H(2) 2.409 ? . . H(1) H(13) 2.233 ? . 2_647 H(1) H(15) 2.493 ? . 1_556 H(1) H(18) 3.058 ? . 2_657 H(1) H(19) 3.326 ? . 2_647 H(1) H(19) 3.207 ? . 2_657 H(1) H(20) 3.137 ? . 2_647 H(2) O(6) 3.259 ? . 1_546 H(2) N(1) 3.465 ? . 1_545 H(2) N(1) 3.412 ? . . H(2) C(1) 2.209 ? . . H(2) C(3) 2.061 ? . . H(2) C(3) 3.411 ? . 2_748 H(2) C(4) 3.310 ? . . H(2) C(4) 3.219 ? . 2_748 H(2) C(15) 3.177 ? . 1_546 H(2) H(1) 2.409 ? . . H(2) H(3) 2.417 ? . . H(2) H(3) 3.115 ? . 2_748 H(2) H(4) 2.982 ? . 2_748 H(2) H(15) 3.447 ? . 1_546 H(2) H(15) 3.473 ? . 1_556 H(2) H(16) 2.321 ? . 1_546 H(2) H(20) 3.441 ? . 1_546 H(3) N(2) 3.353 ? . 1_545 H(3) C(1) 3.306 ? . . H(3) C(2) 2.137 ? . . H(3) C(2) 3.290 ? . 2_748 H(3) C(3) 3.031 ? . 2_748 H(3) C(4) 2.002 ? . . H(3) C(4) 3.164 ? . 2_748 H(3) C(5) 3.244 ? . . H(3) C(5) 3.546 ? . 2_748 H(3) C(6) 3.441 ? . 1_545 H(3) H(2) 2.417 ? . . H(3) H(2) 3.115 ? . 2_758 H(3) H(3) 3.261 ? . 2_748 H(3) H(3) 3.261 ? . 2_758 H(3) H(4) 2.350 ? . . H(3) H(16) 2.844 ? . 2_747 H(4) O(1) 3.580 ? . 2_747 H(4) N(1) 3.300 ? . . H(4) N(2) 3.532 ? . 1_545 H(4) N(2) 2.563 ? . . H(4) N(3) 3.221 ? . 1_545 H(4) N(4) 3.591 ? . 1_545 H(4) C(2) 3.328 ? . . H(4) C(3) 2.123 ? . . H(4) C(5) 2.068 ? . . H(4) C(6) 2.635 ? . . H(4) C(15) 3.391 ? . 2_747 H(4) H(2) 2.982 ? . 2_758 H(4) H(3) 2.350 ? . . H(4) H(8) 3.537 ? . 2_747 H(4) H(9) 3.521 ? . 2_747 H(4) H(16) 2.361 ? . 2_747 H(5) O(2) 2.834 ? . . H(5) O(3) 3.434 ? . . H(5) O(4) 2.170 ? . 2_657 H(5) N(1) 2.983 ? . . H(5) N(2) 3.168 ? . . H(5) N(3) 3.106 ? . . H(5) N(4) 1.985 ? . . H(5) C(5) 3.033 ? . . H(5) C(6) 2.167 ? . . H(5) C(8) 2.718 ? . . H(5) C(9) 3.306 ? . . H(5) C(12) 3.399 ? . 2_657 H(5) H(6) 2.540 ? . . H(5) H(11) 3.370 ? . 2_657 H(5) H(17) 2.626 ? . . H(5) H(18) 2.343 ? . 2_657 H(6) O(2) 2.441 ? . . H(6) O(3) 2.483 ? . 1_565 H(6) N(3) 3.215 ? . . H(6) N(4) 2.023 ? . . H(6) C(7) 2.681 ? . . H(6) C(9) 2.072 ? . . H(6) C(10) 3.260 ? . 1_565 H(6) C(11) 3.262 ? . 1_565 H(6) H(5) 2.540 ? . . H(6) H(7) 1.772 ? . . H(6) H(8) 2.438 ? . . H(6) H(9) 2.855 ? . . H(6) H(10) 2.616 ? . 1_565 H(6) H(12) 3.056 ? . 1_565 H(6) H(17) 3.008 ? . 1_565 H(7) O(2) 3.228 ? . . H(7) N(2) 3.331 ? . 2_757 H(7) N(3) 2.439 ? . . H(7) N(3) 2.687 ? . 2_757 H(7) N(4) 1.972 ? . . H(7) N(4) 3.318 ? . 2_757 H(7) C(7) 3.242 ? . . H(7) C(8) 3.552 ? . 2_757 H(7) C(9) 2.046 ? . . H(7) C(9) 3.249 ? . 2_757 H(7) H(6) 1.772 ? . . H(7) H(7) 3.353 ? . 2_747 H(7) H(7) 3.353 ? . 2_757 H(7) H(8) 2.330 ? . . H(7) H(9) 2.407 ? . . H(7) H(9) 2.411 ? . 2_757 H(7) H(10) 2.851 ? . 1_565 H(8) O(1) 2.653 ? . . H(8) O(2) 2.005 ? . . H(8) N(2) 2.692 ? . 2_757 H(8) N(3) 2.856 ? . 2_757 H(8) N(4) 3.308 ? . . H(8) C(8) 2.081 ? . . H(8) C(10) 2.768 ? . . H(8) C(10) 3.295 ? . 1_565 H(8) C(11) 3.594 ? . 1_565 H(8) C(12) 3.200 ? . 1_565 H(8) C(14) 3.424 ? . 1_565 H(8) H(4) 3.537 ? . 2_757 H(8) H(6) 2.438 ? . . H(8) H(7) 2.330 ? . . H(8) H(9) 1.684 ? . . H(8) H(10) 3.133 ? . . H(8) H(10) 2.454 ? . 1_565 H(8) H(12) 2.290 ? . 1_565 H(8) H(14) 2.556 ? . 1_565 H(9) O(1) 2.852 ? . . H(9) O(2) 1.934 ? . . H(9) N(2) 3.270 ? . 2_757 H(9) N(3) 3.032 ? . . H(9) N(3) 2.969 ? . 2_747 H(9) N(3) 3.590 ? . 2_757 H(9) N(4) 2.546 ? . . H(9) N(4) 3.540 ? . 2_747 H(9) C(7) 3.295 ? . . H(9) C(8) 2.069 ? . . H(9) C(8) 3.337 ? . 2_747 H(9) C(10) 2.400 ? . . H(9) H(4) 3.521 ? . 2_757 H(9) H(6) 2.855 ? . . H(9) H(7) 2.407 ? . . H(9) H(7) 2.411 ? . 2_747 H(9) H(8) 1.684 ? . . H(9) H(10) 2.200 ? . . H(10) O(1) 1.988 ? . . H(10) O(2) 1.984 ? . . H(10) O(3) 2.655 ? . . H(10) N(2) 3.556 ? . 2_747 H(10) N(3) 2.904 ? . 2_747 H(10) C(8) 2.927 ? . 1_545 H(10) C(9) 3.112 ? . 1_545 H(10) C(9) 2.564 ? . . H(10) C(11) 2.123 ? . . H(10) C(12) 2.753 ? . . H(10) C(13) 3.210 ? . . H(10) C(14) 2.542 ? . . H(10) H(6) 2.616 ? . 1_545 H(10) H(7) 2.851 ? . 1_545 H(10) H(8) 2.454 ? . 1_545 H(10) H(8) 3.133 ? . . H(10) H(9) 2.200 ? . . H(10) H(11) 2.855 ? . . H(10) H(12) 2.532 ? . . H(10) H(14) 2.306 ? . . H(10) H(17) 3.086 ? . . H(11) O(1) 2.619 ? . . H(11) O(2) 2.466 ? . . H(11) O(3) 1.957 ? . . H(11) O(3) 2.679 ? . 2_657 H(11) O(4) 2.590 ? . . H(11) O(4) 3.307 ? . 1_565 H(11) C(10) 2.008 ? . . H(11) C(12) 2.079 ? . . H(11) C(13) 2.744 ? . . H(11) C(14) 3.244 ? . . H(11) H(5) 3.370 ? . 2_647 H(11) H(10) 2.855 ? . . H(11) H(12) 2.823 ? . . H(11) H(12) 3.217 ? . 1_565 H(11) H(13) 2.654 ? . . H(11) H(17) 2.121 ? . . H(11) H(17) 3.536 ? . 2_647 H(11) H(17) 2.888 ? . 2_657 H(11) H(18) 3.296 ? . . H(11) H(18) 3.239 ? . 1_565 H(12) O(1) 2.868 ? . 1_545 H(12) O(1) 3.169 ? . . H(12) O(2) 2.480 ? . 1_545 H(12) O(3) 2.499 ? . . H(12) O(4) 2.032 ? . . H(12) O(5) 2.621 ? . . H(12) C(8) 3.469 ? . 1_545 H(12) C(9) 2.803 ? . 1_545 H(12) C(10) 3.148 ? . 1_545 H(12) C(10) 2.651 ? . . H(12) C(11) 2.021 ? . . H(12) C(13) 2.077 ? . . H(12) C(14) 2.671 ? . . H(12) H(6) 3.056 ? . 1_545 H(12) H(8) 2.290 ? . 1_545 H(12) H(10) 2.532 ? . . H(12) H(11) 3.217 ? . 1_545 H(12) H(11) 2.823 ? . . H(12) H(13) 2.865 ? . . H(12) H(14) 2.437 ? . . H(12) H(17) 3.483 ? . . H(12) H(17) 3.045 ? . 2_647 H(12) H(18) 2.408 ? . . H(12) H(19) 3.320 ? . . H(12) H(20) 3.511 ? . 1_545 H(13) O(1) 2.608 ? . . H(13) O(4) 2.624 ? . . H(13) O(5) 1.921 ? . . H(13) O(6) 2.669 ? . . H(13) O(6) 3.431 ? . 2_646 H(13) C(1) 3.003 ? . 2_657 H(13) C(10) 3.210 ? . . H(13) C(11) 2.742 ? . . H(13) C(12) 2.065 ? . . H(13) C(14) 2.069 ? . . H(13) C(15) 2.749 ? . . H(13) H(1) 2.233 ? . 2_657 H(13) H(11) 2.654 ? . . H(13) H(12) 2.865 ? . . H(13) H(14) 2.872 ? . . H(13) H(15) 3.090 ? . . H(13) H(18) 2.597 ? . . H(13) H(19) 2.021 ? . . H(13) H(20) 2.755 ? . . H(14) O(1) 2.040 ? . . H(14) O(5) 2.652 ? . . H(14) O(6) 3.313 ? . . H(14) N(2) 3.069 ? . 2_747 H(14) N(3) 3.258 ? . 2_747 H(14) C(9) 3.566 ? . 1_545 H(14) C(10) 2.549 ? . . H(14) C(11) 3.160 ? . . H(14) C(12) 2.649 ? . . H(14) C(13) 2.081 ? . . H(14) C(15) 2.081 ? . . H(14) H(8) 2.556 ? . 1_545 H(14) H(10) 2.306 ? . . H(14) H(12) 2.437 ? . . H(14) H(13) 2.872 ? . . H(14) H(15) 2.338 ? . . H(14) H(16) 2.529 ? . . H(14) H(19) 3.217 ? . . H(14) H(20) 3.397 ? . 1_545 H(14) H(20) 3.544 ? . . H(15) O(1) 3.242 ? . . H(15) O(5) 2.716 ? . . H(15) O(5) 3.284 ? . 2_656 H(15) O(6) 1.984 ? . . H(15) O(6) 3.215 ? . 2_646 H(15) N(1) 3.495 ? . 1_554 H(15) C(1) 2.795 ? . 1_554 H(15) C(2) 3.323 ? . 1_554 H(15) C(13) 2.790 ? . . H(15) C(14) 2.068 ? . . H(15) H(1) 2.493 ? . 1_554 H(15) H(2) 3.473 ? . 1_554 H(15) H(2) 3.447 ? . 1_564 H(15) H(13) 3.090 ? . . H(15) H(14) 2.338 ? . . H(15) H(16) 1.741 ? . . H(15) H(19) 2.751 ? . . H(15) H(19) 2.700 ? . 2_656 H(15) H(20) 3.340 ? . 1_545 H(15) H(20) 2.692 ? . . H(15) H(20) 3.238 ? . 2_646 H(16) O(1) 2.656 ? . . H(16) O(6) 2.068 ? . . H(16) C(2) 3.375 ? . 1_564 H(16) C(3) 3.401 ? . 2_757 H(16) C(4) 3.104 ? . 2_757 H(16) C(13) 3.556 ? . . H(16) C(14) 2.220 ? . . H(16) H(2) 2.321 ? . 1_564 H(16) H(3) 2.844 ? . 2_757 H(16) H(4) 2.361 ? . 2_757 H(16) H(14) 2.529 ? . . H(16) H(15) 1.741 ? . . H(16) H(19) 3.399 ? . 2_656 H(16) H(20) 2.330 ? . . H(17) O(2) 2.605 ? . . H(17) O(3) 2.693 ? . 2_657 H(17) O(4) 1.968 ? . 2_657 H(17) C(7) 3.268 ? . . H(17) C(10) 2.702 ? . . H(17) C(11) 1.968 ? . . H(17) C(11) 3.257 ? . 2_657 H(17) C(12) 3.258 ? . . H(17) C(12) 2.913 ? . 2_657 H(17) H(5) 2.626 ? . . H(17) H(6) 3.008 ? . 1_545 H(17) H(10) 3.086 ? . . H(17) H(11) 2.121 ? . . H(17) H(11) 2.888 ? . 2_647 H(17) H(11) 3.536 ? . 2_657 H(17) H(12) 3.483 ? . . H(17) H(12) 3.045 ? . 2_657 H(17) H(17) 3.380 ? . 2_647 H(17) H(17) 3.380 ? . 2_657 H(17) H(18) 2.512 ? . 2_657 H(18) O(3) 3.323 ? . 2_647 H(18) O(5) 2.433 ? . . H(18) N(1) 2.321 ? . 2_647 H(18) C(1) 3.106 ? . 2_647 H(18) C(5) 3.345 ? . 2_647 H(18) C(6) 3.517 ? . 2_647 H(18) C(7) 3.035 ? . 2_647 H(18) C(11) 3.120 ? . . H(18) C(12) 1.896 ? . . H(18) C(13) 2.446 ? . . H(18) H(1) 3.058 ? . 2_647 H(18) H(5) 2.343 ? . 2_647 H(18) H(11) 3.239 ? . 1_545 H(18) H(11) 3.296 ? . . H(18) H(12) 2.408 ? . . H(18) H(13) 2.597 ? . . H(18) H(17) 2.512 ? . 2_647 H(18) H(19) 2.717 ? . . H(19) O(4) 3.254 ? . . H(19) O(6) 2.808 ? . 1_545 H(19) O(6) 3.337 ? . . H(19) O(6) 1.998 ? . 2_646 H(19) C(12) 2.965 ? . . H(19) C(13) 1.860 ? . . H(19) C(14) 2.867 ? . . H(19) C(15) 3.118 ? . . H(19) C(15) 2.884 ? . 2_646 H(19) H(1) 3.207 ? . 2_647 H(19) H(1) 3.326 ? . 2_657 H(19) H(12) 3.320 ? . . H(19) H(13) 2.021 ? . . H(19) H(14) 3.217 ? . . H(19) H(15) 2.751 ? . . H(19) H(15) 2.700 ? . 2_646 H(19) H(16) 3.399 ? . 2_646 H(19) H(18) 2.717 ? . . H(19) H(20) 2.145 ? . 1_545 H(19) H(20) 2.652 ? . 2_646 H(20) O(1) 2.591 ? . . H(20) O(5) 1.910 ? . 1_565 H(20) O(5) 3.330 ? . 2_656 H(20) O(6) 3.280 ? . 2_656 H(20) C(13) 3.161 ? . . H(20) C(13) 3.171 ? . 1_565 H(20) C(14) 2.601 ? . . H(20) C(15) 1.900 ? . . H(20) H(1) 3.137 ? . 2_657 H(20) H(2) 3.441 ? . 1_564 H(20) H(12) 3.511 ? . 1_565 H(20) H(13) 2.755 ? . . H(20) H(14) 3.544 ? . . H(20) H(14) 3.397 ? . 1_565 H(20) H(15) 2.692 ? . . H(20) H(15) 3.340 ? . 1_565 H(20) H(15) 3.238 ? . 2_656 H(20) H(16) 2.330 ? . . H(20) H(19) 2.145 ? . 1_565 H(20) H(19) 2.652 ? . 2_656