# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Cytidine_(Rigaku_Master_fo #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C22 H18 N2 O4' _chemical_formula_moiety 'C22 H18 N2 O4' _chemical_formula_weight 374.40 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,+Y,1/2-Z 3 -X,-Y,-Z 4 +X,-Y,1/2+Z 5 1/2+X,1/2+Y,+Z 6 1/2-X,1/2+Y,1/2-Z 7 1/2-X,1/2-Y,-Z 8 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 27.567(8) _cell_length_b 9.156(3) _cell_length_c 13.752(14) _cell_angle_alpha 90.0000 _cell_angle_beta 97.93(5) _cell_angle_gamma 90.0000 _cell_volume 3438(4) _cell_formula_units_Z 8 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15.44 _cell_measurement_theta_max 17.45 _cell_measurement_temperature 298 #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568.00 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type none #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 298 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w _diffrn_reflns_number 5843 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_theta_max 30.03 _diffrn_reflns_theta_full 30.04 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 10 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -0.187 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 5022 _reflns_number_gt 3320 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1603 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 5022 _refine_ls_number_parameters 253 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0914P)^2^+0.4792P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.240 _refine_diff_density_min -0.380 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; 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 O9 O 0.15825(4) 0.20757(11) 0.16696(10) 0.0612(4) Uani 1.0 8 d . . . O10 O -0.06486(4) 0.59495(11) 0.10429(10) 0.0606(4) Uani 1.0 8 d . . . O18 O 0.07543(4) -0.21845(10) 0.13852(9) 0.0516(3) Uani 1.0 8 d . . . O28 O -0.14643(3) 0.16459(11) 0.04549(8) 0.0484(3) Uani 1.0 8 d . . . N2 N 0.11646(4) -0.00535(11) 0.17529(8) 0.0381(3) Uani 1.0 8 d . . . N16 N -0.10700(4) 0.38128(11) 0.07968(8) 0.0394(3) Uani 1.0 8 d . . . C1 C -0.01713(4) 0.22710(13) 0.11469(8) 0.0320(3) Uani 1.0 8 d . . . C2 C 0.02754(4) 0.14932(12) 0.13300(8) 0.0323(3) Uani 1.0 8 d . . . C3 C 0.02695(4) -0.00478(13) 0.13256(9) 0.0346(3) Uani 1.0 8 d . . . C4 C 0.07207(4) 0.22767(13) 0.14877(9) 0.0353(3) Uani 1.0 8 d . . . C5 C -0.01674(4) 0.38091(13) 0.11579(9) 0.0354(3) Uani 1.0 8 d . . . C6 C -0.06147(4) 0.14874(13) 0.09492(9) 0.0339(3) Uani 1.0 8 d . . . C7 C -0.10824(4) 0.22905(13) 0.07090(9) 0.0365(3) Uani 1.0 8 d . . . C8 C 0.11909(5) 0.14640(14) 0.16415(10) 0.0401(3) Uani 1.0 8 d . . . C11 C -0.01689(5) -0.07897(13) 0.11480(10) 0.0388(3) Uani 1.0 8 d . . . C12 C 0.07153(5) 0.37793(13) 0.14875(11) 0.0422(3) Uani 1.0 8 d . . . C13 C -0.06366(5) 0.46271(13) 0.09994(10) 0.0399(3) Uani 1.0 8 d . . . C14 C -0.06117(5) -0.00153(13) 0.09568(10) 0.0383(3) Uani 1.0 8 d . . . C15 C 0.07390(5) -0.08665(13) 0.14874(9) 0.0376(3) Uani 1.0 8 d . . . C17 C 0.02714(5) 0.45522(13) 0.13311(11) 0.0422(3) Uani 1.0 8 d . . . C19 C -0.15389(5) 0.46307(14) 0.06592(11) 0.0455(4) Uani 1.0 8 d . . . C20 C 0.16316(5) -0.08529(14) 0.20015(11) 0.0411(3) Uani 1.0 8 d . . . C21 C 0.16262(6) -0.22447(16) 0.26200(13) 0.0524(4) Uani 1.0 8 d . . . C22 C 0.20130(5) -0.02200(16) 0.28127(13) 0.0543(4) Uani 1.0 8 d . . . C23 C -0.23134(6) 0.4622(2) 0.03120(14) 0.0637(5) Uani 1.0 8 d . . . C24 C -0.19584(5) 0.41835(18) 0.12237(12) 0.0543(4) Uani 1.0 8 d . . . C25 C -0.18895(6) 0.45452(19) -0.03064(13) 0.0563(4) Uani 1.0 8 d . . . C26 C 0.21313(7) -0.17931(18) 0.31560(16) 0.0685(5) Uani 1.0 8 d . . . H11 H -0.0171 -0.1805 0.1155 0.0466 Uiso 1.0 8 calc R . . H12 H 0.1010 0.4290 0.1592 0.0506 Uiso 1.0 8 calc R . . H14 H -0.0906 -0.0524 0.0834 0.0460 Uiso 1.0 8 calc R . . H17 H 0.0273 0.5568 0.1344 0.0506 Uiso 1.0 8 calc R . . H19 H -0.1465 0.5663 0.0799 0.0546 Uiso 1.0 8 calc R . . H20 H 0.1781 -0.1047 0.1408 0.0494 Uiso 1.0 8 calc R . . H21A H 0.1630 -0.3141 0.2245 0.0628 Uiso 1.0 8 calc R . . H21B H 0.1370 -0.2264 0.3037 0.0628 Uiso 1.0 8 calc R . . H22A H 0.2283 0.0278 0.2569 0.0651 Uiso 1.0 8 calc R . . H22B H 0.1874 0.0375 0.3288 0.0651 Uiso 1.0 8 calc R . . H23A H -0.2449 0.5594 0.0352 0.0765 Uiso 1.0 8 calc R . . H23B H -0.2570 0.3911 0.0123 0.0765 Uiso 1.0 8 calc R . . H24A H -0.1964 0.3151 0.1379 0.0652 Uiso 1.0 8 calc R . . H24B H -0.1984 0.4778 0.1798 0.0652 Uiso 1.0 8 calc R . . H25A H -0.1873 0.3633 -0.0658 0.0675 Uiso 1.0 8 calc R . . H25B H -0.1871 0.5377 -0.0736 0.0675 Uiso 1.0 8 calc R . . H26A H 0.2167 -0.1919 0.3863 0.0822 Uiso 1.0 8 calc R . . H26B H 0.2405 -0.2224 0.2885 0.0822 Uiso 1.0 8 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O9 0.0339(5) 0.0406(6) 0.1075(10) -0.0074(4) 0.0045(6) 0.0124(6) O10 0.0435(6) 0.0288(5) 0.1082(10) -0.0021(4) 0.0059(6) -0.0052(5) O18 0.0500(6) 0.0279(5) 0.0743(7) -0.0025(4) -0.0005(5) -0.0020(5) O28 0.0331(5) 0.0412(5) 0.0696(7) -0.0090(4) 0.0021(5) -0.0063(5) N2 0.0347(5) 0.0292(5) 0.0499(6) -0.0021(4) 0.0043(5) 0.0013(5) N16 0.0328(5) 0.0317(5) 0.0531(7) -0.0032(4) 0.0042(5) -0.0047(5) C1 0.0326(6) 0.0275(5) 0.0357(6) -0.0065(4) 0.0040(5) -0.0010(5) C2 0.0342(6) 0.0266(5) 0.0358(6) -0.0062(4) 0.0040(5) -0.0003(5) C3 0.0375(6) 0.0268(5) 0.0392(6) -0.0058(5) 0.0046(5) 0.0009(5) C4 0.0327(6) 0.0293(6) 0.0437(7) -0.0064(5) 0.0040(5) 0.0022(5) C5 0.0355(6) 0.0272(6) 0.0433(7) -0.0045(5) 0.0044(5) -0.0012(5) C6 0.0337(6) 0.0301(6) 0.0378(6) -0.0073(5) 0.0050(5) -0.0020(5) C7 0.0335(6) 0.0333(6) 0.0428(7) -0.0061(5) 0.0057(5) -0.0031(5) C8 0.0358(6) 0.0311(6) 0.0529(8) -0.0044(5) 0.0043(6) 0.0025(6) C11 0.0417(7) 0.0258(6) 0.0483(7) -0.0092(5) 0.0044(6) 0.0006(5) C12 0.0346(6) 0.0286(6) 0.0625(9) -0.0089(5) 0.0038(6) 0.0008(6) C13 0.0369(6) 0.0303(6) 0.0523(8) -0.0047(5) 0.0055(6) -0.0032(5) C14 0.0365(6) 0.0306(6) 0.0478(7) -0.0108(5) 0.0054(5) -0.0012(5) C15 0.0407(7) 0.0294(6) 0.0423(7) -0.0055(5) 0.0040(5) 0.0012(5) C17 0.0382(7) 0.0261(6) 0.0615(9) -0.0071(5) 0.0040(6) -0.0005(5) C19 0.0343(6) 0.0353(7) 0.0662(9) 0.0007(5) 0.0040(6) -0.0048(6) C20 0.0369(6) 0.0341(6) 0.0530(8) 0.0035(5) 0.0083(6) -0.0021(6) C21 0.0533(8) 0.0375(7) 0.0649(10) 0.0057(6) 0.0030(7) 0.0040(7) C22 0.0419(8) 0.0410(7) 0.0765(11) 0.0050(6) -0.0037(7) -0.0065(7) C23 0.0372(8) 0.0663(11) 0.0859(13) 0.0016(7) 0.0019(8) -0.0043(9) C24 0.0449(8) 0.0546(9) 0.0653(10) 0.0040(7) 0.0139(7) -0.0073(8) C25 0.0474(8) 0.0546(9) 0.0652(10) 0.0035(7) 0.0019(7) 0.0068(8) C26 0.0595(10) 0.0479(9) 0.0910(14) 0.0124(7) -0.0146(9) 0.0004(9) #============================================================================== _computing_data_collection WinAFC _computing_cell_refinement WinAFC _computing_data_reduction WinAFC _computing_structure_solution 'Il Milione (Burla, et al., 2007)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # 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 O9 C8 1.2120(18) yes . . O10 C13 1.2129(17) yes . . O18 C15 1.2163(16) yes . . O28 C7 1.2154(15) yes . . N2 C8 1.4008(17) yes . . N2 C15 1.3949(18) yes . . N2 C20 1.4794(18) yes . . N16 C7 1.3990(17) yes . . N16 C13 1.4032(18) yes . . N16 C19 1.4832(18) yes . . C1 C2 1.4147(16) yes . . C1 C5 1.4084(18) yes . . C1 C6 1.4110(17) yes . . C2 C3 1.4110(17) yes . . C2 C4 1.4125(16) yes . . C3 C11 1.3785(18) yes . . C3 C15 1.4856(18) yes . . C4 C8 1.4842(18) yes . . C4 C12 1.3758(18) yes . . C5 C13 1.4845(18) yes . . C5 C17 1.3796(18) yes . . C6 C7 1.4814(17) yes . . C6 C14 1.3759(18) yes . . C11 C14 1.4048(19) yes . . C12 C17 1.4042(19) yes . . C19 C24 1.535(3) yes . . C19 C25 1.533(3) yes . . C20 C21 1.533(3) yes . . C20 C22 1.537(3) yes . . C21 C26 1.539(3) yes . . C22 C26 1.537(3) yes . . C23 C24 1.534(3) yes . . C23 C25 1.539(3) yes . . C11 H11 0.930 no . . C12 H12 0.930 no . . C14 H14 0.930 no . . C17 H17 0.930 no . . C19 H19 0.980 no . . C20 H20 0.980 no . . C21 H21A 0.970 no . . C21 H21B 0.970 no . . C22 H22A 0.970 no . . C22 H22B 0.970 no . . C23 H23A 0.970 no . . C23 H23B 0.970 no . . C24 H24A 0.970 no . . C24 H24B 0.970 no . . C25 H25A 0.970 no . . C25 H25B 0.970 no . . C26 H26A 0.970 no . . C26 H26B 0.970 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 C8 N2 C15 123.71(11) yes . . . C8 N2 C20 117.35(11) yes . . . C15 N2 C20 118.05(11) yes . . . C7 N16 C13 123.81(11) yes . . . C7 N16 C19 118.78(10) yes . . . C13 N16 C19 117.40(11) yes . . . C2 C1 C5 119.75(10) yes . . . C2 C1 C6 119.21(11) yes . . . C5 C1 C6 121.04(11) yes . . . C1 C2 C3 119.56(10) yes . . . C1 C2 C4 119.23(11) yes . . . C3 C2 C4 121.18(11) yes . . . C2 C3 C11 120.19(11) yes . . . C2 C3 C15 119.64(10) yes . . . C11 C3 C15 120.15(11) yes . . . C2 C4 C8 119.38(11) yes . . . C2 C4 C12 119.91(11) yes . . . C8 C4 C12 120.70(11) yes . . . C1 C5 C13 119.85(10) yes . . . C1 C5 C17 120.01(11) yes . . . C13 C5 C17 120.13(11) yes . . . C1 C6 C7 119.65(11) yes . . . C1 C6 C14 120.19(11) yes . . . C7 C6 C14 120.14(11) yes . . . O28 C7 N16 121.23(11) yes . . . O28 C7 C6 121.05(12) yes . . . N16 C7 C6 117.72(10) yes . . . O9 C8 N2 120.94(13) yes . . . O9 C8 C4 121.96(12) yes . . . N2 C8 C4 117.10(12) yes . . . C3 C11 C14 120.16(12) yes . . . C4 C12 C17 120.87(12) yes . . . O10 C13 N16 120.79(13) yes . . . O10 C13 C5 121.70(12) yes . . . N16 C13 C5 117.51(11) yes . . . C6 C14 C11 120.68(12) yes . . . O18 C15 N2 121.22(13) yes . . . O18 C15 C3 121.78(12) yes . . . N2 C15 C3 116.99(11) yes . . . C5 C17 C12 120.18(12) yes . . . N16 C19 C24 120.33(12) yes . . . N16 C19 C25 121.27(13) yes . . . C24 C19 C25 89.74(13) yes . . . N2 C20 C21 117.69(13) yes . . . N2 C20 C22 117.88(12) yes . . . C21 C20 C22 88.21(12) yes . . . C20 C21 C26 88.00(13) yes . . . C20 C22 C26 87.97(12) yes . . . C24 C23 C25 89.55(14) yes . . . C19 C24 C23 87.53(14) yes . . . C19 C25 C23 87.42(14) yes . . . C21 C26 C22 88.00(13) yes . . . C3 C11 H11 119.915 no . . . C14 C11 H11 119.926 no . . . C4 C12 H12 119.569 no . . . C17 C12 H12 119.560 no . . . C6 C14 H14 119.664 no . . . C11 C14 H14 119.652 no . . . C5 C17 H17 119.925 no . . . C12 C17 H17 119.895 no . . . N16 C19 H19 107.944 no . . . C24 C19 H19 107.965 no . . . C25 C19 H19 107.958 no . . . N2 C20 H20 110.444 no . . . C21 C20 H20 110.434 no . . . C22 C20 H20 110.422 no . . . C20 C21 H21A 113.990 no . . . C20 C21 H21B 113.977 no . . . C26 C21 H21A 113.992 no . . . C26 C21 H21B 113.988 no . . . H21A C21 H21B 111.179 no . . . C20 C22 H22A 113.999 no . . . C20 C22 H22B 113.980 no . . . C26 C22 H22A 113.995 no . . . C26 C22 H22B 113.987 no . . . H22A C22 H22B 111.187 no . . . C24 C23 H23A 113.718 no . . . C24 C23 H23B 113.715 no . . . C25 C23 H23A 113.720 no . . . C25 C23 H23B 113.723 no . . . H23A C23 H23B 110.966 no . . . C19 C24 H24A 114.068 no . . . C19 C24 H24B 114.067 no . . . C23 C24 H24A 114.062 no . . . C23 C24 H24B 114.067 no . . . H24A C24 H24B 111.241 no . . . C19 C25 H25A 114.085 no . . . C19 C25 H25B 114.081 no . . . C23 C25 H25A 114.077 no . . . C23 C25 H25B 114.089 no . . . H25A C25 H25B 111.261 no . . . C21 C26 H26A 113.997 no . . . C21 C26 H26B 113.991 no . . . C22 C26 H26A 113.989 no . . . C22 C26 H26B 113.980 no . . . H26A C26 H26B 111.171 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 C8 N2 C15 O18 163.09(12) no . . . . C8 N2 C15 C3 -16.25(18) no . . . . C15 N2 C8 O9 -163.16(12) no . . . . C15 N2 C8 C4 16.76(18) no . . . . C8 N2 C20 C21 149.28(11) no . . . . C8 N2 C20 C22 45.53(17) no . . . . C20 N2 C8 O9 5.83(19) no . . . . C20 N2 C8 C4 -174.25(11) no . . . . C15 N2 C20 C21 -41.10(17) no . . . . C15 N2 C20 C22 -144.84(11) no . . . . C20 N2 C15 O18 -5.83(18) no . . . . C20 N2 C15 C3 174.83(10) no . . . . C7 N16 C13 O10 178.16(12) no . . . . C7 N16 C13 C5 -1.92(18) no . . . . C13 N16 C7 O28 -173.98(12) no . . . . C13 N16 C7 C6 6.81(18) no . . . . C7 N16 C19 C24 50.96(17) no . . . . C7 N16 C19 C25 -59.47(16) no . . . . C19 N16 C7 O28 5.33(18) no . . . . C19 N16 C7 C6 -173.87(10) no . . . . C13 N16 C19 C24 -129.68(12) no . . . . C13 N16 C19 C25 119.89(13) no . . . . C19 N16 C13 O10 -1.17(19) no . . . . C19 N16 C13 C5 178.76(11) no . . . . C2 C1 C5 C13 -177.94(10) no . . . . C2 C1 C5 C17 1.04(17) no . . . . C5 C1 C2 C3 179.52(10) no . . . . C5 C1 C2 C4 -2.19(16) no . . . . C2 C1 C6 C7 -177.05(10) no . . . . C2 C1 C6 C14 1.44(17) no . . . . C6 C1 C2 C3 -0.89(16) no . . . . C6 C1 C2 C4 177.40(10) no . . . . C5 C1 C6 C7 2.53(17) no . . . . C5 C1 C6 C14 -178.98(10) no . . . . C6 C1 C5 C13 2.49(17) no . . . . C6 C1 C5 C17 -178.54(10) no . . . . C1 C2 C3 C11 -0.27(17) no . . . . C1 C2 C3 C15 178.13(10) no . . . . C1 C2 C4 C8 -177.64(10) no . . . . C1 C2 C4 C12 1.70(17) no . . . . C3 C2 C4 C8 0.62(17) no . . . . C3 C2 C4 C12 179.96(10) no . . . . C4 C2 C3 C11 -178.52(10) no . . . . C4 C2 C3 C15 -0.12(17) no . . . . C2 C3 C11 C14 0.89(19) no . . . . C2 C3 C15 O18 -171.94(11) no . . . . C2 C3 C15 N2 7.40(17) no . . . . C11 C3 C15 O18 6.46(19) no . . . . C11 C3 C15 N2 -174.20(11) no . . . . C15 C3 C11 C14 -177.50(11) no . . . . C2 C4 C8 O9 171.55(11) no . . . . C2 C4 C8 N2 -8.37(18) no . . . . C2 C4 C12 C17 -0.1(2) no . . . . C8 C4 C12 C17 179.27(12) no . . . . C12 C4 C8 O9 -7.8(2) no . . . . C12 C4 C8 N2 172.29(12) no . . . . C1 C5 C13 O10 176.99(12) no . . . . C1 C5 C13 N16 -2.93(18) no . . . . C1 C5 C17 C12 0.6(2) no . . . . C13 C5 C17 C12 179.58(11) no . . . . C17 C5 C13 O10 -2.0(2) no . . . . C17 C5 C13 N16 178.09(12) no . . . . C1 C6 C7 O28 173.72(11) no . . . . C1 C6 C7 N16 -7.07(17) no . . . . C1 C6 C14 C11 -0.82(19) no . . . . C7 C6 C14 C11 177.65(11) no . . . . C14 C6 C7 O28 -4.76(19) no . . . . C14 C6 C7 N16 174.45(11) no . . . . C3 C11 C14 C6 -0.4(2) no . . . . C4 C12 C17 C5 -1.1(3) no . . . . N16 C19 C24 C23 -144.83(11) no . . . . N16 C19 C25 C23 144.01(12) no . . . . C24 C19 C25 C23 17.99(10) no . . . . C25 C19 C24 C23 -18.05(10) no . . . . N2 C20 C21 C26 -141.73(12) no . . . . N2 C20 C22 C26 141.60(12) no . . . . C21 C20 C22 C26 20.98(11) no . . . . C22 C20 C21 C26 -20.94(10) no . . . . C20 C21 C26 C22 20.95(12) no . . . . C20 C22 C26 C21 -20.90(12) no . . . . C24 C23 C25 C19 -18.00(11) no . . . . C25 C23 C24 C19 17.98(11) no . . . . 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 O9 C12 2.8365(19) no . . O9 C15 3.5448(19) no . . O9 C20 2.7202(19) no . . O9 C22 2.790(3) no . . O10 C7 3.5655(19) no . . O10 C17 2.8193(19) no . . O10 C19 2.7208(19) no . . O18 C8 3.552(2) no . . O18 C11 2.8258(19) no . . O18 C20 2.7364(19) no . . O18 C21 2.745(3) no . . O28 C13 3.5701(18) no . . O28 C14 2.8047(18) no . . O28 C19 2.7578(19) no . . O28 C23 3.580(3) no . . O28 C24 2.961(2) no . . O28 C25 3.030(3) no . . N2 C2 2.8212(17) no . . N2 C26 3.456(3) no . . N16 C1 2.8343(17) no . . N16 C23 3.480(3) no . . C1 C11 2.802(2) no . . C1 C12 2.7900(19) no . . C2 C14 2.7937(19) no . . C2 C17 2.8008(19) no . . C3 C6 2.7994(18) no . . C3 C8 2.8726(19) no . . C4 C5 2.8039(18) no . . C4 C15 2.878(2) no . . C5 C7 2.8718(18) no . . C6 C13 2.876(2) no . . C7 C24 3.132(2) no . . C7 C25 3.210(3) no . . C8 C22 3.017(3) no . . C15 C21 2.991(3) no . . O9 C24 3.516(3) no . 2_555 O10 C11 3.2604(19) no . 1_565 O10 C12 3.468(4) no . 3_565 O10 C17 3.590(4) no . 3_565 O18 O28 3.442(3) no . 3_555 O18 N16 3.564(3) no . 3_555 O18 C6 3.243(4) no . 3_555 O18 C7 3.137(4) no . 3_555 O18 C17 3.2676(18) no . 1_545 O28 O18 3.442(3) no . 3_555 O28 N2 3.566(3) no . 3_555 O28 C20 3.424(4) no . 3_555 O28 C22 3.446(3) no . 2_555 O28 C23 3.582(3) no . 7_455 N2 O28 3.566(3) no . 3_555 N16 O18 3.564(3) no . 3_555 C1 C2 3.592(4) no . 2_555 C2 C1 3.592(4) no . 2_555 C2 C11 3.441(4) no . 3_555 C3 C11 3.588(4) no . 2_555 C3 C11 3.461(4) no . 3_555 C3 C14 3.400(4) no . 3_555 C5 C17 3.570(4) no . 2_555 C6 O18 3.243(4) no . 3_555 C6 C15 3.369(4) no . 3_555 C7 O18 3.137(4) no . 3_555 C7 C15 3.537(4) no . 3_555 C11 O10 3.2604(19) no . 1_545 C11 C2 3.441(4) no . 3_555 C11 C3 3.588(4) no . 2_555 C11 C3 3.461(4) no . 3_555 C12 O10 3.468(4) no . 3_565 C12 C13 3.578(4) no . 2_555 C13 C12 3.578(4) no . 2_555 C13 C17 3.569(4) no . 3_565 C14 C3 3.400(4) no . 3_555 C14 C15 3.427(4) no . 3_555 C15 C6 3.369(4) no . 3_555 C15 C7 3.537(4) no . 3_555 C15 C14 3.427(4) no . 3_555 C17 O10 3.590(4) no . 3_565 C17 O18 3.2676(18) no . 1_565 C17 C5 3.570(4) no . 2_555 C17 C13 3.569(4) no . 3_565 C20 O28 3.424(4) no . 3_555 C22 O28 3.446(3) no . 2_555 C23 O28 3.582(3) no . 7_455 C24 O9 3.516(3) no . 2_555 O9 H12 2.5632 no . . O9 H20 2.9421 no . . O9 H22A 2.7026 no . . O9 H22B 2.7440 no . . O10 H17 2.5421 no . . O10 H19 2.2449 no . . O18 H11 2.5517 no . . O18 H20 3.0121 no . . O18 H21A 2.6840 no . . O18 H21B 2.6420 no . . O28 H14 2.5232 no . . O28 H24A 2.4281 no . . O28 H25A 2.5383 no . . N2 H21A 3.1392 no . . N2 H21B 2.6939 no . . N2 H22A 3.1456 no . . N2 H22B 2.7008 no . . N16 H24A 2.7620 no . . N16 H24B 3.1607 no . . N16 H25A 2.7756 no . . N16 H25B 3.1763 no . . C1 H14 3.2544 no . . C1 H17 3.2550 no . . C2 H11 3.2581 no . . C2 H12 3.2528 no . . C3 H14 3.2465 no . . C4 H17 3.2515 no . . C5 H12 3.2468 no . . C6 H11 3.2506 no . . C7 H14 2.6234 no . . C7 H19 3.2707 no . . C7 H24A 2.8277 no . . C7 H25A 2.9426 no . . C8 H12 2.6343 no . . C8 H20 2.8597 no . . C8 H22A 3.2867 no . . C8 H22B 2.9135 no . . C13 H17 2.6325 no . . C13 H19 2.4531 no . . C15 H11 2.6328 no . . C15 H20 2.8944 no . . C15 H21A 3.2784 no . . C15 H21B 2.8598 no . . C19 H23A 2.6390 no . . C19 H23B 2.9116 no . . C20 H26A 2.9386 no . . C20 H26B 2.6233 no . . C21 H22A 2.9409 no . . C21 H22B 2.6251 no . . C22 H21A 2.9411 no . . C22 H21B 2.6252 no . . C23 H19 2.5283 no . . C24 H25A 2.6792 no . . C24 H25B 2.9489 no . . C25 H24A 2.6790 no . . C25 H24B 2.9492 no . . C26 H20 2.5572 no . . H11 H14 2.3288 no . . H12 H17 2.3266 no . . H19 H23A 2.6990 no . . H19 H23B 3.4540 no . . H19 H24A 2.8497 no . . H19 H24B 2.2662 no . . H19 H25A 2.8482 no . . H19 H25B 2.2642 no . . H20 H21A 2.3041 no . . H20 H21B 2.8721 no . . H20 H22A 2.3076 no . . H20 H22B 2.8748 no . . H20 H26A 3.4891 no . . H20 H26B 2.6987 no . . H21A H22B 3.5508 no . . H21A H26A 2.7351 no . . H21A H26B 2.3505 no . . H21B H22A 3.5508 no . . H21B H22B 2.7848 no . . H21B H26A 2.3506 no . . H21B H26B 2.8903 no . . H22A H26A 2.7328 no . . H22A H26B 2.3474 no . . H22B H26A 2.3475 no . . H22B H26B 2.8877 no . . H23A H24A 2.8757 no . . H23A H24B 2.3351 no . . H23A H25A 2.8800 no . . H23A H25B 2.3404 no . . H23B H24A 2.3369 no . . H23B H24B 2.7410 no . . H23B H25A 2.3423 no . . H23B H25B 2.7456 no . . H24A H25A 2.8817 no . . H24A H25B 3.5903 no . . H24B H25A 3.5907 no . . H24B H25B 3.5839 no . . O9 H24A 2.9149 no . 2_555 O9 H24B 3.3386 no . 2_555 O9 H25B 2.8284 no . 3_565 O9 H26B 2.8472 no . 6_555 O10 H11 2.4337 no . 1_565 O10 H14 3.3101 no . 1_565 O10 H21B 2.9872 no . 2_565 O18 H12 3.3076 no . 1_545 O18 H17 2.4447 no . 1_545 O28 H20 2.6471 no . 3_555 O28 H22B 2.4808 no . 2_555 O28 H23B 2.7197 no . 7_455 N2 H14 3.5156 no . 2_555 N2 H14 3.5698 no . 3_555 N16 H12 3.5980 no . 2_555 C1 H11 3.4525 no . 3_555 C2 H11 3.4016 no . 3_555 C5 H17 3.4603 no . 3_565 C7 H20 3.4543 no . 3_555 C7 H22B 3.2507 no . 2_555 C8 H14 3.4942 no . 3_555 C8 H24A 3.5688 no . 2_555 C11 H17 3.5484 no . 1_545 C12 H25B 3.5670 no . 3_565 C13 H11 3.5047 no . 1_565 C13 H17 3.5090 no . 3_565 C14 H21B 3.3638 no . 2_555 C15 H14 3.5253 no . 3_555 C15 H17 3.5037 no . 1_545 C17 H11 3.5482 no . 1_565 C19 H21A 3.5681 no . 2_565 C19 H21B 3.3596 no . 2_565 C20 H25A 3.2662 no . 3_555 C21 H14 3.4802 no . 2_555 C21 H19 2.9767 no . 2_545 C21 H24B 2.9713 no . 2_545 C21 H25A 3.1398 no . 3_555 C22 H23B 3.4417 no . 8_555 C22 H24A 3.2893 no . 2_555 C22 H24B 3.2632 no . 5_545 C22 H25B 3.4311 no . 8_555 C22 H26B 3.3830 no . 6_555 C23 H20 3.1490 no . 5_455 C23 H22A 3.4916 no . 5_455 C23 H22B 3.3236 no . 8_454 C23 H23B 3.2979 no . 7_455 C23 H26A 3.3696 no . 2_565 C23 H26A 3.1080 no . 8_454 C24 H20 3.5253 no . 5_455 C24 H21A 3.2755 no . 2_565 C24 H22A 3.1426 no . 5_455 C24 H22B 3.5523 no . 2_555 C24 H23B 3.5335 no . 7_455 C24 H26B 3.3266 no . 5_455 C25 H12 3.3664 no . 3_565 C25 H20 3.5734 no . 3_555 C25 H21A 3.1303 no . 3_555 C25 H22A 3.4540 no . 8_454 C25 H23B 3.5218 no . 7_455 C25 H26A 3.4612 no . 8_454 C26 H19 3.4047 no . 2_545 C26 H22A 3.3528 no . 6_545 C26 H23A 3.1946 no . 2_545 C26 H23A 3.2704 no . 8_555 C26 H24B 3.1671 no . 2_545 C26 H24B 3.5713 no . 5_545 C26 H25B 3.2261 no . 8_555 H11 O10 2.4337 no . 1_545 H11 C1 3.4525 no . 3_555 H11 C2 3.4016 no . 3_555 H11 C13 3.5047 no . 1_545 H11 C17 3.5482 no . 1_545 H11 H17 2.6959 no . 1_545 H12 O18 3.3076 no . 1_565 H12 N16 3.5980 no . 2_555 H12 C25 3.3664 no . 3_565 H12 H21A 2.9732 no . 1_565 H12 H24B 3.2685 no . 2_555 H12 H25A 3.4308 no . 3_565 H12 H25B 2.8092 no . 3_565 H14 O10 3.3101 no . 1_545 H14 N2 3.5156 no . 2_555 H14 N2 3.5698 no . 3_555 H14 C8 3.4942 no . 3_555 H14 C15 3.5253 no . 3_555 H14 C21 3.4802 no . 2_555 H14 H21B 2.6704 no . 2_555 H14 H22B 3.1851 no . 2_555 H17 O18 2.4447 no . 1_565 H17 C5 3.4603 no . 3_565 H17 C11 3.5484 no . 1_565 H17 C13 3.5090 no . 3_565 H17 C15 3.5037 no . 1_565 H17 H11 2.6959 no . 1_565 H19 C21 2.9767 no . 2_565 H19 C26 3.4047 no . 2_565 H19 H21A 2.9963 no . 2_565 H19 H21B 2.4738 no . 2_565 H19 H26A 3.0178 no . 2_565 H20 O28 2.6471 no . 3_555 H20 C7 3.4543 no . 3_555 H20 C23 3.1490 no . 5_545 H20 C24 3.5253 no . 5_545 H20 C25 3.5734 no . 3_555 H20 H23A 3.1172 no . 5_545 H20 H23B 2.6825 no . 5_545 H20 H24A 3.5421 no . 5_545 H20 H24B 3.4548 no . 5_545 H20 H25A 2.6082 no . 3_555 H21A C19 3.5681 no . 2_545 H21A C24 3.2755 no . 2_545 H21A C25 3.1303 no . 3_555 H21A H12 2.9732 no . 1_545 H21A H19 2.9963 no . 2_545 H21A H22A 3.3073 no . 6_545 H21A H24B 2.4418 no . 2_545 H21A H25A 2.4111 no . 3_555 H21A H25B 3.0530 no . 3_555 H21B O10 2.9872 no . 2_545 H21B C14 3.3638 no . 2_555 H21B C19 3.3596 no . 2_545 H21B H14 2.6704 no . 2_555 H21B H19 2.4738 no . 2_545 H21B H24B 3.1866 no . 2_545 H22A C23 3.4916 no . 5_545 H22A C24 3.1426 no . 5_545 H22A C25 3.4540 no . 8_555 H22A C26 3.3528 no . 6_555 H22A H21A 3.3073 no . 6_555 H22A H23A 3.2482 no . 5_545 H22A H23B 3.5576 no . 8_555 H22A H24A 3.1826 no . 2_555 H22A H24A 3.4240 no . 5_545 H22A H24B 2.4514 no . 5_545 H22A H25A 3.2856 no . 8_555 H22A H25B 3.1200 no . 8_555 H22A H26B 2.5517 no . 6_555 H22B O28 2.4808 no . 2_555 H22B C7 3.2507 no . 2_555 H22B C23 3.3236 no . 8_555 H22B C24 3.5523 no . 2_555 H22B H14 3.1851 no . 2_555 H22B H23A 3.2958 no . 8_555 H22B H23B 2.8424 no . 8_555 H22B H24A 2.5880 no . 2_555 H22B H26B 3.5032 no . 6_555 H23A C26 3.1946 no . 2_565 H23A C26 3.2704 no . 8_454 H23A H20 3.1172 no . 5_455 H23A H22A 3.2482 no . 5_455 H23A H22B 3.2958 no . 8_454 H23A H26A 2.5938 no . 2_565 H23A H26A 2.4874 no . 8_454 H23A H26B 3.1310 no . 2_565 H23B O28 2.7197 no . 7_455 H23B C22 3.4417 no . 8_454 H23B C23 3.2979 no . 7_455 H23B C24 3.5335 no . 7_455 H23B C25 3.5218 no . 7_455 H23B H20 2.6825 no . 5_455 H23B H22A 3.5576 no . 8_454 H23B H22B 2.8424 no . 8_454 H23B H23B 2.6414 no . 7_455 H23B H24A 2.9582 no . 7_455 H23B H25A 2.9395 no . 7_455 H23B H26A 3.2815 no . 8_454 H24A O9 2.9149 no . 2_555 H24A C8 3.5688 no . 2_555 H24A C22 3.2893 no . 2_555 H24A H20 3.5421 no . 5_455 H24A H22A 3.1826 no . 2_555 H24A H22A 3.4240 no . 5_455 H24A H22B 2.5880 no . 2_555 H24A H23B 2.9582 no . 7_455 H24A H26B 2.9026 no . 5_455 H24B O9 3.3386 no . 2_555 H24B C21 2.9713 no . 2_565 H24B C22 3.2632 no . 5_455 H24B C26 3.1671 no . 2_565 H24B C26 3.5713 no . 5_455 H24B H12 3.2685 no . 2_555 H24B H20 3.4548 no . 5_455 H24B H21A 2.4418 no . 2_565 H24B H21B 3.1866 no . 2_565 H24B H22A 2.4514 no . 5_455 H24B H25B 3.3651 no . 4_565 H24B H26A 3.1777 no . 2_565 H24B H26B 3.0343 no . 2_565 H24B H26B 3.0202 no . 5_455 H25A C20 3.2662 no . 3_555 H25A C21 3.1398 no . 3_555 H25A H12 3.4308 no . 3_565 H25A H20 2.6082 no . 3_555 H25A H21A 2.4111 no . 3_555 H25A H22A 3.2856 no . 8_454 H25A H23B 2.9395 no . 7_455 H25A H26B 3.4573 no . 3_555 H25B O9 2.8284 no . 3_565 H25B C12 3.5670 no . 3_565 H25B C22 3.4311 no . 8_454 H25B C26 3.2261 no . 8_454 H25B H12 2.8092 no . 3_565 H25B H21A 3.0530 no . 3_555 H25B H22A 3.1200 no . 8_454 H25B H24B 3.3651 no . 4_564 H25B H26A 2.9884 no . 8_454 H25B H26B 3.0648 no . 8_454 H26A C23 3.3696 no . 2_545 H26A C23 3.1080 no . 8_555 H26A C25 3.4612 no . 8_555 H26A H19 3.0178 no . 2_545 H26A H23A 2.5938 no . 2_545 H26A H23A 2.4874 no . 8_555 H26A H23B 3.2815 no . 8_555 H26A H24B 3.1777 no . 2_545 H26A H25B 2.9884 no . 8_555 H26A H26A 3.5655 no . 7_546 H26B O9 2.8472 no . 6_545 H26B C22 3.3830 no . 6_545 H26B C24 3.3266 no . 5_545 H26B H22A 2.5517 no . 6_545 H26B H22B 3.5032 no . 6_545 H26B H23A 3.1310 no . 2_545 H26B H24A 2.9026 no . 5_545 H26B H24B 3.0343 no . 2_545 H26B H24B 3.0202 no . 5_545 H26B H25A 3.4573 no . 3_555 H26B H25B 3.0648 no . 8_555 #============================================================================== #============================================================================== # 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 #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 939277' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data__sample3 #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C24 H22 N2 O4' _chemical_formula_moiety 'C24 H22 N2 O4' _chemical_formula_weight 402.45 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z #------------------------------------------------------------------------------ _cell_length_a 6.0407(18) _cell_length_b 16.750(6) _cell_length_c 5.2404(19) _cell_angle_alpha 98.72(5) _cell_angle_beta 104.53(5) _cell_angle_gamma 74.80(5) _cell_volume 493.2(4) _cell_formula_units_Z 1 _cell_measurement_reflns_used 1459 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 29.77 _cell_measurement_temperature 293 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 212.00 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.318 _exptl_absorpt_correction_T_max 0.982 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 293 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _diffrn_measurement_device_type 'Rigaku Mercury70' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.629 _diffrn_reflns_number 2466 _diffrn_reflns_av_R_equivalents 0.0540 _diffrn_reflns_theta_max 30.59 _diffrn_reflns_theta_full 30.59 _diffrn_measured_fraction_theta_max 0.813 _diffrn_measured_fraction_theta_full 0.813 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2466 _reflns_number_gt 911 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0664 _refine_ls_wR_factor_ref 0.1502 _refine_ls_number_restraints ? _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2466 _refine_ls_number_parameters 147 _refine_ls_goodness_of_fit_ref 1.257 _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/\s^2^(Fo^2^)' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.354 _refine_diff_density_min -0.342 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; 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(2) O 0.2615(4) 0.75045(12) 0.3630(5) 0.0648(8) Uani 1.0 2 d . . . O(3) O -0.0393(4) 0.62973(11) 0.8781(5) 0.0596(7) Uani 1.0 2 d . . . N(1) N 0.1142(4) 0.69262(13) 0.6290(5) 0.0504(8) Uani 1.0 2 d . . . C(1) C 0.4291(5) 0.60815(16) 0.4136(6) 0.0406(8) Uani 1.0 2 d . . . C(2) C 0.2611(5) 0.54267(16) 0.6811(6) 0.0402(8) Uani 1.0 2 d . . . C(3) C 0.4217(4) 0.53776(14) 0.5240(6) 0.0375(8) Uani 1.0 2 d . . . C(5) C 0.0993(5) 0.62356(17) 0.7400(6) 0.0471(9) Uani 1.0 2 d . . . C(6) C 0.2557(5) 0.47321(16) 0.7865(6) 0.0464(9) Uani 1.0 2 d . . . C(7) C 0.2648(5) 0.68867(18) 0.4615(6) 0.0481(10) Uani 1.0 2 d . . . C(8) C 0.5879(5) 0.60256(16) 0.2626(6) 0.0473(9) Uani 1.0 2 d . . . C(9) C -0.0441(7) 0.77383(18) 0.6891(8) 0.0741(13) Uani 1.0 2 d . . . C(10) C 0.0824(8) 0.8427(2) 0.8180(8) 0.1046(17) Uani 1.0 2 d . . . C(11) C -0.2254(6) 0.8084(2) 0.4445(9) 0.0910(16) Uani 1.0 2 d . . . C(12) C -0.2520(10) 0.9007(3) 0.4931(14) 0.155(3) Uani 1.0 2 d . . . C(13) C -0.0609(15) 0.9160(3) 0.6826(13) 0.228(4) Uani 1.0 2 d . . . H(1) H 0.1486 0.4770 0.8905 0.0583 Uiso 1.0 2 calc R . . H(2) H 0.5928 0.6498 0.1928 0.0594 Uiso 1.0 2 calc R . . H(3) H -0.1318 0.7660 0.8137 0.0954 Uiso 1.0 2 calc R . . H(4) H 0.0972 0.8519 1.0082 0.1261 Uiso 1.0 2 calc R . . H(5) H 0.2374 0.8288 0.7789 0.1261 Uiso 1.0 2 calc R . . H(6) H -0.1636 0.7879 0.2868 0.1094 Uiso 1.0 2 calc R . . H(7) H -0.3748 0.7940 0.4225 0.1095 Uiso 1.0 2 calc R . . H(8) H -0.2521 0.9286 0.3438 0.1772 Uiso 1.0 2 calc R . . H(9) H -0.3876 0.9301 0.5647 0.1773 Uiso 1.0 2 calc R . . H(10) H -0.1363 0.9596 0.7985 0.2440 Uiso 1.0 2 calc R . . H(11) H 0.0151 0.9411 0.5841 0.2441 Uiso 1.0 2 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(2) 0.0707(15) 0.0481(13) 0.0880(19) -0.0127(11) 0.0324(14) 0.0214(12) O(3) 0.0668(14) 0.0534(13) 0.0703(17) -0.0123(11) 0.0387(13) 0.0048(11) N(1) 0.0607(16) 0.0391(14) 0.0600(18) -0.0111(12) 0.0289(14) 0.0055(12) C(1) 0.0428(15) 0.0408(15) 0.0419(18) -0.0129(13) 0.0116(14) 0.0056(13) C(2) 0.0420(15) 0.0412(16) 0.0419(18) -0.0138(13) 0.0116(14) 0.0063(13) C(3) 0.0388(14) 0.0410(15) 0.0365(17) -0.0164(12) 0.0069(13) 0.0051(13) C(5) 0.0533(17) 0.0493(17) 0.046(2) -0.0194(15) 0.0157(16) 0.0074(15) C(6) 0.0474(17) 0.0496(17) 0.049(2) -0.0167(14) 0.0148(15) 0.0102(15) C(7) 0.0498(16) 0.0515(19) 0.050(2) -0.0181(15) 0.0154(16) 0.0090(16) C(8) 0.0524(17) 0.0446(17) 0.052(2) -0.0176(14) 0.0135(16) 0.0114(15) C(9) 0.106(3) 0.0388(18) 0.094(3) -0.0058(19) 0.067(3) 0.0017(19) C(10) 0.183(5) 0.052(3) 0.080(4) -0.028(3) 0.040(4) -0.008(3) C(11) 0.064(3) 0.056(3) 0.153(5) -0.0001(19) 0.034(3) 0.019(3) C(12) 0.169(6) 0.041(3) 0.232(8) 0.008(3) 0.036(5) 0.019(4) C(13) 0.407(10) 0.046(4) 0.157(7) -0.058(5) -0.090(7) 0.035(4) #============================================================================== _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2006)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'Il Milione (Burla, et al., 2007)' _computing_structure_refinement 'CRYSTALS (Carruthers, et al., 1999)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # 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(2) C(7) 1.218(5) yes . . O(3) C(5) 1.213(5) yes . . N(1) C(5) 1.404(5) yes . . N(1) C(7) 1.398(5) yes . . N(1) C(9) 1.484(4) yes . . C(1) C(3) 1.405(5) yes . . C(1) C(7) 1.479(4) yes . . C(1) C(8) 1.366(5) yes . . C(2) C(3) 1.402(5) yes . . C(2) C(5) 1.489(4) yes . . C(2) C(6) 1.372(5) yes . . C(3) C(3) 1.398(3) yes . 2_666 C(6) C(8) 1.401(4) yes . 2_666 C(9) C(10) 1.529(6) yes . . C(9) C(11) 1.538(5) yes . . C(10) C(13) 1.470(7) yes . . C(11) C(12) 1.500(6) yes . . C(12) C(13) 1.374(9) yes . . C(6) H(1) 0.930 no . . C(8) H(2) 0.930 no . . C(9) H(3) 0.980 no . . C(10) H(4) 0.970 no . . C(10) H(5) 0.970 no . . C(11) H(6) 0.970 no . . C(11) H(7) 0.970 no . . C(12) H(8) 0.970 no . . C(12) H(9) 0.970 no . . C(13) H(10) 0.970 no . . C(13) H(11) 0.970 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(5) N(1) C(7) 123.8(3) yes . . . C(5) N(1) C(9) 117.6(3) yes . . . C(7) N(1) C(9) 118.6(3) yes . . . C(3) C(1) C(7) 119.9(3) yes . . . C(3) C(1) C(8) 120.3(3) yes . . . C(7) C(1) C(8) 119.8(3) yes . . . C(3) C(2) C(5) 120.3(3) yes . . . C(3) C(2) C(6) 120.1(3) yes . . . C(5) C(2) C(6) 119.6(3) yes . . . C(1) C(3) C(2) 120.9(3) yes . . . C(1) C(3) C(3) 119.0(3) yes . . 2_666 C(2) C(3) C(3) 120.1(3) yes . . 2_666 O(3) C(5) N(1) 121.3(3) yes . . . O(3) C(5) C(2) 121.6(3) yes . . . N(1) C(5) C(2) 117.1(3) yes . . . C(2) C(6) C(8) 119.8(3) yes . . 2_666 O(2) C(7) N(1) 120.3(3) yes . . . O(2) C(7) C(1) 121.8(3) yes . . . N(1) C(7) C(1) 117.9(3) yes . . . C(1) C(8) C(6) 120.8(3) yes . . 2_666 N(1) C(9) C(10) 114.5(3) yes . . . N(1) C(9) C(11) 113.5(3) yes . . . C(10) C(9) C(11) 106.2(3) yes . . . C(9) C(10) C(13) 103.9(4) yes . . . C(9) C(11) C(12) 104.4(4) yes . . . C(11) C(12) C(13) 108.2(4) yes . . . C(10) C(13) C(12) 113.7(5) yes . . . C(2) C(6) H(1) 119.554 no . . . C(8) C(6) H(1) 120.690 no 2_666 . . C(1) C(8) H(2) 119.488 no . . . C(6) C(8) H(2) 119.728 no 2_666 . . N(1) C(9) H(3) 107.958 no . . . C(10) C(9) H(3) 106.962 no . . . C(11) C(9) H(3) 107.363 no . . . C(9) C(10) H(4) 113.094 no . . . C(9) C(10) H(5) 109.153 no . . . C(13) C(10) H(4) 112.151 no . . . C(13) C(10) H(5) 108.859 no . . . H(4) C(10) H(5) 109.495 no . . . C(9) C(11) H(6) 109.842 no . . . C(9) C(11) H(7) 112.451 no . . . C(12) C(11) H(6) 109.478 no . . . C(12) C(11) H(7) 111.106 no . . . H(6) C(11) H(7) 109.472 no . . . C(11) C(12) H(8) 115.958 no . . . C(11) C(12) H(9) 114.177 no . . . C(13) C(12) H(8) 104.322 no . . . C(13) C(12) H(9) 105.056 no . . . H(8) C(12) H(9) 108.125 no . . . C(10) C(13) H(10) 113.359 no . . . C(10) C(13) H(11) 117.056 no . . . C(12) C(13) H(10) 101.263 no . . . C(12) C(13) H(11) 101.945 no . . . H(10) C(13) H(11) 107.760 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(5) N(1) C(7) O(2) 176.9(3) no . . . . C(5) N(1) C(7) C(1) -4.3(4) no . . . . C(7) N(1) C(5) O(3) -177.8(3) no . . . . C(7) N(1) C(5) C(2) 2.3(4) no . . . . C(5) N(1) C(9) C(10) 122.7(3) no . . . . C(5) N(1) C(9) C(11) -115.1(3) no . . . . C(9) N(1) C(5) O(3) 0.7(4) no . . . . C(9) N(1) C(5) C(2) -179.2(3) no . . . . C(7) N(1) C(9) C(10) -58.7(4) no . . . . C(7) N(1) C(9) C(11) 63.4(4) no . . . . C(9) N(1) C(7) O(2) -1.6(4) no . . . . C(9) N(1) C(7) C(1) 177.2(3) no . . . . C(3) C(1) C(7) O(2) -177.9(3) no . . . . C(3) C(1) C(7) N(1) 3.3(4) no . . . . C(7) C(1) C(3) C(2) -0.4(4) no . . . . C(7) C(1) C(3) C(3) 179.9(2) no . . . 2_666 C(3) C(1) C(8) C(6) 0.5(4) no . . . 2_666 C(8) C(1) C(3) C(2) 179.5(2) no . . . . C(8) C(1) C(3) C(3) -0.3(4) no . . . 2_666 C(7) C(1) C(8) C(6) -179.6(2) no . . . 2_666 C(8) C(1) C(7) O(2) 2.3(4) no . . . . C(8) C(1) C(7) N(1) -176.5(3) no . . . . C(3) C(2) C(5) O(3) -179.1(3) no . . . . C(3) C(2) C(5) N(1) 0.9(4) no . . . . C(5) C(2) C(3) C(1) -1.7(4) no . . . . C(5) C(2) C(3) C(3) 178.0(2) no . . . 2_666 C(3) C(2) C(6) C(8) 0.2(4) no . . . 2_666 C(6) C(2) C(3) C(1) 179.8(2) no . . . . C(6) C(2) C(3) C(3) -0.5(4) no . . . 2_666 C(5) C(2) C(6) C(8) -178.3(2) no . . . 2_666 C(6) C(2) C(5) O(3) -0.5(4) no . . . . C(6) C(2) C(5) N(1) 179.4(2) no . . . . C(1) C(3) C(3) C(1) -180(358250) no . . 2_666 2_666 C(1) C(3) C(3) C(2) -0.3(4) no . . 2_666 2_666 C(2) C(3) C(3) C(1) 0.3(4) no . . 2_666 2_666 C(2) C(3) C(3) C(2) 180(358250) no . . 2_666 2_666 C(2) C(6) C(8) C(1) 0.3(4) no . . 2_666 2_666 N(1) C(9) C(10) C(13) 137.8(3) no . . . . N(1) C(9) C(11) C(12) -144.9(3) no . . . . C(10) C(9) C(11) C(12) -18.3(4) no . . . . C(11) C(9) C(10) C(13) 11.7(4) no . . . . C(9) C(10) C(13) C(12) -0.2(7) no . . . . C(9) C(11) C(12) C(13) 18.5(6) no . . . . C(11) C(12) C(13) C(10) -11.8(9) no . . . . 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(2) C(5) 3.566(5) no . . O(2) C(8) 2.805(4) no . . O(2) C(9) 2.735(6) no . . O(2) C(10) 2.922(5) no . . O(2) C(11) 2.963(5) no . . O(2) C(12) 3.587(6) no . . O(2) C(13) 3.417(7) no . . O(3) C(6) 2.807(4) no . . O(3) C(7) 3.568(5) no . . O(3) C(9) 2.735(5) no . . N(1) C(3) 2.835(4) no . . N(1) C(13) 3.598(6) no . . C(1) C(2) 2.781(4) no . 2_666 C(1) C(5) 2.876(5) no . . C(2) C(7) 2.864(5) no . . C(3) C(6) 2.791(5) no . 2_666 C(3) C(8) 2.771(5) no . 2_666 C(5) C(11) 3.546(5) no . . C(7) C(10) 3.072(5) no . . C(7) C(11) 3.099(5) no . . O(2) O(3) 3.449(4) no . 1_554 O(2) C(9) 3.578(5) no . 1_554 O(2) C(10) 3.259(5) no . 1_554 O(2) C(11) 3.394(5) no . 1_655 O(3) O(2) 3.449(4) no . 1_556 O(3) C(1) 3.576(4) no . 1_455 O(3) C(1) 3.435(4) no . 1_556 O(3) C(6) 3.321(5) no . 2_567 O(3) C(7) 3.303(4) no . 1_556 O(3) C(8) 3.483(4) no . 1_455 O(3) C(8) 3.526(5) no . 1_456 C(1) O(3) 3.435(4) no . 1_554 C(1) O(3) 3.576(4) no . 1_655 C(2) C(6) 3.496(4) no . 2_566 C(2) C(6) 3.479(4) no . 2_667 C(2) C(8) 3.359(4) no . 1_556 C(5) C(6) 3.513(5) no . 2_566 C(5) C(8) 3.514(4) no . 1_455 C(5) C(8) 3.468(4) no . 1_556 C(6) O(3) 3.321(5) no . 2_567 C(6) C(2) 3.496(4) no . 2_566 C(6) C(2) 3.479(4) no . 2_667 C(6) C(5) 3.513(5) no . 2_566 C(6) C(6) 3.462(4) no . 2_667 C(7) O(3) 3.303(4) no . 1_554 C(8) O(3) 3.526(5) no . 1_654 C(8) O(3) 3.483(4) no . 1_655 C(8) C(2) 3.359(4) no . 1_554 C(8) C(5) 3.468(4) no . 1_554 C(8) C(5) 3.514(4) no . 1_655 C(9) O(2) 3.578(5) no . 1_556 C(10) O(2) 3.259(5) no . 1_556 C(11) O(2) 3.394(5) no . 1_455 O(2) H(2) 2.5131 no . . O(2) H(5) 2.3839 no . . O(2) H(6) 2.4215 no . . O(2) H(11) 3.3171 no . . O(3) H(1) 2.5151 no . . O(3) H(3) 2.2599 no . . N(1) H(4) 3.0705 no . . N(1) H(5) 2.5353 no . . N(1) H(6) 2.5556 no . . N(1) H(7) 3.0168 no . . C(1) H(1) 3.2441 no . 2_666 C(2) H(2) 3.2349 no . 2_666 C(3) H(1) 3.2419 no . . C(3) H(2) 3.2409 no . . C(5) H(1) 2.6118 no . . C(5) H(3) 2.4569 no . . C(7) H(2) 2.6032 no . . C(7) H(3) 3.2700 no . . C(7) H(5) 2.6557 no . . C(7) H(6) 2.7046 no . . C(9) H(8) 3.1849 no . . C(9) H(9) 2.9273 no . . C(9) H(10) 3.0059 no . . C(9) H(11) 3.0612 no . . C(10) H(6) 2.9434 no . . C(10) H(7) 3.2229 no . . C(10) H(8) 3.0609 no . . C(10) H(9) 2.9131 no . . C(11) H(4) 3.2027 no . . C(11) H(5) 2.9773 no . . C(11) H(10) 2.9899 no . . C(11) H(11) 2.8729 no . . C(12) H(3) 2.8490 no . . C(12) H(4) 3.0515 no . . C(12) H(5) 2.9820 no . . C(13) H(3) 2.8632 no . . C(13) H(6) 2.8265 no . . C(13) H(7) 3.0853 no . . H(1) H(2) 2.3371 no . 2_666 H(3) H(4) 2.2165 no . . H(3) H(5) 2.7583 no . . H(3) H(6) 2.7928 no . . H(3) H(7) 2.2355 no . . H(3) H(9) 3.0806 no . . H(3) H(10) 3.2492 no . . H(4) H(9) 3.3450 no . . H(4) H(10) 2.2231 no . . H(4) H(11) 2.7352 no . . H(5) H(6) 3.1918 no . . H(5) H(8) 3.4518 no . . H(5) H(10) 2.7136 no . . H(5) H(11) 2.2253 no . . H(6) H(8) 2.2654 no . . H(6) H(9) 2.8050 no . . H(6) H(11) 3.0941 no . . H(7) H(8) 2.6678 no . . H(7) H(9) 2.2760 no . . H(7) H(10) 3.5604 no . . H(8) H(10) 2.3275 no . . H(8) H(11) 1.8201 no . . H(9) H(10) 1.8247 no . . H(9) H(11) 2.4636 no . . O(2) H(3) 3.2354 no . 1_554 O(2) H(4) 2.5451 no . 1_554 O(2) H(5) 3.4656 no . 1_554 O(2) H(7) 2.4253 no . 1_655 O(3) H(1) 2.6042 no . 2_567 O(3) H(2) 3.0088 no . 1_456 O(3) H(6) 3.1959 no . 1_556 N(1) H(2) 3.5688 no . 1_455 N(1) H(2) 3.5876 no . 1_556 C(1) H(7) 3.5988 no . 1_655 C(2) H(1) 3.4078 no . 2_566 C(2) H(2) 3.4858 no . 1_556 C(3) H(1) 3.4476 no . 1_554 C(3) H(1) 3.4798 no . 2_667 C(5) H(1) 3.5491 no . 2_567 C(5) H(2) 3.3953 no . 1_556 C(6) H(1) 3.1785 no . 2_567 C(7) H(7) 3.1993 no . 1_655 C(8) H(7) 3.2402 no . 1_655 C(9) H(6) 3.3482 no . 1_556 C(10) H(6) 3.5096 no . 1_556 C(11) H(2) 3.1221 no . 1_455 C(11) H(3) 3.4298 no . 1_554 C(12) H(4) 3.5680 no . 1_554 C(12) H(9) 3.0921 no . 2_476 C(12) H(11) 3.4413 no . 2_576 C(13) H(10) 3.3337 no . 2_577 C(13) H(11) 3.0532 no . 2_576 H(1) O(3) 2.6042 no . 2_567 H(1) C(2) 3.4078 no . 2_566 H(1) C(3) 3.4476 no . 1_556 H(1) C(3) 3.4798 no . 2_667 H(1) C(5) 3.5491 no . 2_567 H(1) C(6) 3.1785 no . 2_567 H(1) H(1) 2.2742 no . 2_567 H(2) O(3) 3.0088 no . 1_654 H(2) N(1) 3.5876 no . 1_554 H(2) N(1) 3.5688 no . 1_655 H(2) C(2) 3.4858 no . 1_554 H(2) C(5) 3.3953 no . 1_554 H(2) C(11) 3.1221 no . 1_655 H(2) H(6) 2.9730 no . 1_655 H(2) H(7) 2.5630 no . 1_655 H(3) O(2) 3.2354 no . 1_556 H(3) C(11) 3.4298 no . 1_556 H(3) H(6) 2.4987 no . 1_556 H(4) O(2) 2.5451 no . 1_556 H(4) C(12) 3.5680 no . 1_556 H(4) H(6) 2.8773 no . 1_556 H(4) H(7) 3.3716 no . 1_656 H(4) H(8) 2.9915 no . 1_556 H(4) H(10) 3.2169 no . 2_577 H(4) H(11) 3.2530 no . 1_556 H(5) O(2) 3.4656 no . 1_556 H(5) H(7) 3.2343 no . 1_655 H(6) O(3) 3.1959 no . 1_554 H(6) C(9) 3.3482 no . 1_554 H(6) C(10) 3.5096 no . 1_554 H(6) H(2) 2.9730 no . 1_455 H(6) H(3) 2.4987 no . 1_554 H(6) H(4) 2.8773 no . 1_554 H(7) O(2) 2.4253 no . 1_455 H(7) C(1) 3.5988 no . 1_455 H(7) C(7) 3.1993 no . 1_455 H(7) C(8) 3.2402 no . 1_455 H(7) H(2) 2.5630 no . 1_455 H(7) H(4) 3.3716 no . 1_454 H(7) H(5) 3.2343 no . 1_455 H(8) H(4) 2.9915 no . 1_554 H(8) H(9) 2.8375 no . 2_476 H(8) H(10) 3.2512 no . 1_554 H(8) H(11) 2.8419 no . 2_576 H(9) C(12) 3.0921 no . 2_476 H(9) H(8) 2.8375 no . 2_476 H(9) H(9) 2.4786 no . 2_476 H(9) H(10) 3.2923 no . 2_476 H(9) H(11) 3.5902 no . 1_455 H(10) C(13) 3.3337 no . 2_577 H(10) H(4) 3.2169 no . 2_577 H(10) H(8) 3.2512 no . 1_556 H(10) H(9) 3.2923 no . 2_476 H(10) H(10) 2.7485 no . 2_577 H(10) H(11) 3.1157 no . 2_576 H(10) H(11) 3.4037 no . 2_577 H(11) C(12) 3.4413 no . 2_576 H(11) C(13) 3.0532 no . 2_576 H(11) H(4) 3.2530 no . 1_554 H(11) H(8) 2.8419 no . 2_576 H(11) H(9) 3.5902 no . 1_655 H(11) H(10) 3.1157 no . 2_576 H(11) H(10) 3.4037 no . 2_577 H(11) H(11) 2.2282 no . 2_576 #============================================================================== #============================================================================== # 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 #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 939278' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data__sample4 #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C28 H30 N2 O4' _chemical_formula_moiety 'C28 H30 N2 O4' _chemical_formula_weight 458.56 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z #------------------------------------------------------------------------------ _cell_length_a 6.211(6) _cell_length_b 17.454(15) _cell_length_c 5.236(6) _cell_angle_alpha 90.85(4) _cell_angle_beta 100.77(4) _cell_angle_gamma 94.30(3) _cell_volume 555.7(10) _cell_formula_units_Z 1 _cell_measurement_reflns_used 1827 _cell_measurement_theta_min 3.35 _cell_measurement_theta_max 30.60 _cell_measurement_temperature 293 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244.00 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.254 _exptl_absorpt_correction_T_max 0.982 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 293 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _diffrn_measurement_device_type 'Rigaku Mercury70' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.629 _diffrn_reflns_number 4273 _diffrn_reflns_av_R_equivalents 0.0888 _diffrn_reflns_theta_max 30.69 _diffrn_reflns_theta_full 30.69 _diffrn_measured_fraction_theta_max 0.815 _diffrn_measured_fraction_theta_full 0.815 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2811 _reflns_number_gt 554 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.1209 _refine_ls_wR_factor_ref 0.4078 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2811 _refine_ls_number_parameters 154 _refine_ls_goodness_of_fit_ref 0.855 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1576P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.340 _refine_diff_density_min -0.420 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; 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 0.0822(8) 0.6222(3) 0.8589(10) 0.0681(15) Uani 1.0 2 d . . . O(2) O 0.4688(8) 0.7288(3) 0.2845(9) 0.0623(14) Uani 1.0 2 d . . . N(1) N 0.2971(9) 0.6789(3) 0.5992(10) 0.0512(14) Uani 1.0 2 d . . . C(1) C 0.2400(11) 0.4769(4) 0.8011(13) 0.0539(17) Uani 1.0 2 d . . . C(2) C 0.2990(10) 0.5402(4) 0.6786(12) 0.0468(15) Uani 1.0 2 d . . . C(3) C 0.4581(10) 0.5361(4) 0.5180(12) 0.0473(15) Uani 1.0 2 d . . . C(4) C 0.5189(10) 0.5992(4) 0.3828(12) 0.0481(16) Uani 1.0 2 d . . . C(5) C 0.6725(11) 0.5926(4) 0.2253(13) 0.0527(17) Uani 1.0 2 d . . . C(6) C 0.2197(11) 0.6155(4) 0.7204(13) 0.0543(17) Uani 1.0 2 d . . . C(7) C 0.4315(11) 0.6742(4) 0.4117(12) 0.0494(16) Uani 1.0 2 d . . . C(8) C 0.2255(10) 0.7569(4) 0.6586(13) 0.0520(17) Uani 1.0 2 d . . . C(9) C 0.4153(11) 0.8184(4) 0.7171(14) 0.0560(18) Uani 1.0 2 d . . . C(10) C 0.3810(12) 0.8799(4) 0.9119(14) 0.063(2) Uani 1.0 2 d . . . C(11) C 0.2125(14) 0.9357(5) 0.8107(15) 0.074(3) Uani 1.0 2 d . . . C(12) C -0.0174(13) 0.8985(5) 0.6962(15) 0.073(3) Uani 1.0 2 d . . . C(13) C -0.0308(12) 0.8566(4) 0.4401(14) 0.069(2) Uani 1.0 2 d . . . C(14) C 0.0315(12) 0.7738(5) 0.4468(15) 0.068(2) Uani 1.0 2 d . . . H(1) H 0.1364 0.4801 0.9075 0.0647 Uiso 1.0 2 calc R . . H(2) H 0.7170 0.6349 0.1370 0.0633 Uiso 1.0 2 calc R . . H(8) H 0.1669 0.7516 0.8193 0.0624 Uiso 1.0 2 calc R . . H(9A) H 0.4344 0.8426 0.5565 0.0672 Uiso 1.0 2 calc R . . H(9B) H 0.5492 0.7943 0.7854 0.0672 Uiso 1.0 2 calc R . . H(10A) H 0.3372 0.8545 1.0599 0.0762 Uiso 1.0 2 calc R . . H(10B) H 0.5208 0.9090 0.9741 0.0762 Uiso 1.0 2 calc R . . H(11A) H 0.2654 0.9659 0.6777 0.0890 Uiso 1.0 2 calc R . . H(11B) H 0.2007 0.9708 0.9520 0.0890 Uiso 1.0 2 calc R . . H(12A) H -0.0624 0.8627 0.8196 0.0877 Uiso 1.0 2 calc R . . H(12B) H -0.1201 0.9382 0.6729 0.0877 Uiso 1.0 2 calc R . . H(13A) H 0.0635 0.8856 0.3417 0.0824 Uiso 1.0 2 calc R . . H(13B) H -0.1803 0.8569 0.3443 0.0824 Uiso 1.0 2 calc R . . H(14A) H 0.0658 0.7602 0.2794 0.0816 Uiso 1.0 2 calc R . . H(14B) H -0.0956 0.7406 0.4696 0.0816 Uiso 1.0 2 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.061(3) 0.067(4) 0.092(4) 0.016(3) 0.048(3) 0.001(3) O(2) 0.070(4) 0.067(4) 0.062(3) 0.025(3) 0.034(3) 0.014(3) N(1) 0.049(3) 0.050(4) 0.062(4) 0.011(3) 0.027(3) 0.005(3) C(1) 0.048(4) 0.055(5) 0.067(4) 0.005(3) 0.032(4) 0.004(4) C(2) 0.036(4) 0.046(4) 0.064(4) 0.005(3) 0.024(3) -0.001(3) C(3) 0.045(4) 0.045(4) 0.058(4) 0.007(3) 0.022(3) 0.006(3) C(4) 0.044(4) 0.050(4) 0.055(4) 0.013(3) 0.018(3) 0.007(3) C(5) 0.049(4) 0.052(4) 0.061(4) 0.003(3) 0.022(3) 0.003(3) C(6) 0.050(4) 0.059(5) 0.061(4) 0.011(4) 0.024(3) 0.004(4) C(7) 0.047(4) 0.053(5) 0.051(4) 0.007(3) 0.018(3) 0.000(3) C(8) 0.052(4) 0.042(4) 0.069(4) 0.007(3) 0.025(4) 0.003(3) C(9) 0.046(4) 0.053(4) 0.072(5) 0.010(3) 0.016(3) 0.000(4) C(10) 0.066(5) 0.057(5) 0.069(5) 0.009(4) 0.016(4) -0.001(4) C(11) 0.093(7) 0.063(5) 0.072(5) 0.025(5) 0.023(5) -0.003(4) C(12) 0.080(6) 0.067(5) 0.081(6) 0.033(4) 0.028(5) 0.002(4) C(13) 0.058(5) 0.080(6) 0.071(5) 0.020(4) 0.016(4) 0.001(4) C(14) 0.053(5) 0.085(6) 0.070(5) 0.022(4) 0.016(4) -0.000(4) #============================================================================== _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2006)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'Il Milione (Burla, et al., 2007)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # 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(6) 1.230(9) yes . . O(2) C(7) 1.204(9) yes . . N(1) C(6) 1.384(9) yes . . N(1) C(7) 1.407(9) yes . . N(1) C(8) 1.508(9) yes . . C(1) C(2) 1.347(10) yes . . C(1) C(5) 1.381(10) yes . 2_666 C(2) C(3) 1.417(10) yes . . C(2) C(6) 1.465(10) yes . . C(3) C(3) 1.422(9) yes . 2_666 C(3) C(4) 1.385(9) yes . . C(4) C(5) 1.383(10) yes . . C(4) C(7) 1.469(10) yes . . C(8) C(9) 1.517(9) yes . . C(8) C(14) 1.527(10) yes . . C(9) C(10) 1.523(10) yes . . C(10) C(11) 1.512(11) yes . . C(11) C(12) 1.532(11) yes . . C(12) C(13) 1.504(11) yes . . C(13) C(14) 1.523(11) yes . . C(1) H(1) 0.930 no . . C(5) H(2) 0.930 no . . C(8) H(8) 0.980 no . . C(9) H(9A) 0.970 no . . C(9) H(9B) 0.970 no . . C(10) H(10A) 0.970 no . . C(10) H(10B) 0.970 no . . C(11) H(11A) 0.970 no . . C(11) H(11B) 0.970 no . . C(12) H(12A) 0.970 no . . C(12) H(12B) 0.970 no . . C(13) H(13A) 0.970 no . . C(13) H(13B) 0.970 no . . C(14) H(14A) 0.970 no . . C(14) H(14B) 0.970 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(6) N(1) C(7) 123.3(6) yes . . . C(6) N(1) C(8) 118.9(6) yes . . . C(7) N(1) C(8) 117.7(6) yes . . . C(2) C(1) C(5) 122.4(7) yes . . 2_666 C(1) C(2) C(3) 119.2(6) yes . . . C(1) C(2) C(6) 122.8(7) yes . . . C(3) C(2) C(6) 117.7(6) yes . . . C(2) C(3) C(3) 118.5(6) yes . . 2_666 C(2) C(3) C(4) 121.1(6) yes . . . C(3) C(3) C(4) 120.3(7) yes 2_666 . . C(3) C(4) C(5) 119.3(6) yes . . . C(3) C(4) C(7) 121.6(6) yes . . . C(5) C(4) C(7) 119.1(6) yes . . . C(1) C(5) C(4) 120.2(7) yes 2_666 . . O(1) C(6) N(1) 120.1(7) yes . . . O(1) C(6) C(2) 120.3(6) yes . . . N(1) C(6) C(2) 119.7(7) yes . . . O(2) C(7) N(1) 120.8(7) yes . . . O(2) C(7) C(4) 123.4(7) yes . . . N(1) C(7) C(4) 115.8(6) yes . . . N(1) C(8) C(9) 113.0(6) yes . . . N(1) C(8) C(14) 108.3(5) yes . . . C(9) C(8) C(14) 116.8(6) yes . . . C(8) C(9) C(10) 113.0(6) yes . . . C(9) C(10) C(11) 115.7(6) yes . . . C(10) C(11) C(12) 115.0(6) yes . . . C(11) C(12) C(13) 113.8(7) yes . . . C(12) C(13) C(14) 117.6(6) yes . . . C(8) C(14) C(13) 115.6(6) yes . . . C(2) C(1) H(1) 118.798 no . . . C(5) C(1) H(1) 118.792 no 2_666 . . C(1) C(5) H(2) 119.915 no 2_666 . . C(4) C(5) H(2) 119.924 no . . . N(1) C(8) H(8) 106.004 no . . . C(9) C(8) H(8) 105.996 no . . . C(14) C(8) H(8) 105.996 no . . . C(8) C(9) H(9A) 108.988 no . . . C(8) C(9) H(9B) 108.989 no . . . C(10) C(9) H(9A) 108.984 no . . . C(10) C(9) H(9B) 108.988 no . . . H(9A) C(9) H(9B) 107.775 no . . . C(9) C(10) H(10A) 108.339 no . . . C(9) C(10) H(10B) 108.343 no . . . C(11) C(10) H(10A) 108.347 no . . . C(11) C(10) H(10B) 108.349 no . . . H(10A) C(10) H(10B) 107.430 no . . . C(10) C(11) H(11A) 108.525 no . . . C(10) C(11) H(11B) 108.527 no . . . C(12) C(11) H(11A) 108.527 no . . . C(12) C(11) H(11B) 108.529 no . . . H(11A) C(11) H(11B) 107.525 no . . . C(11) C(12) H(12A) 108.803 no . . . C(11) C(12) H(12B) 108.805 no . . . C(13) C(12) H(12A) 108.807 no . . . C(13) C(12) H(12B) 108.800 no . . . H(12A) C(12) H(12B) 107.678 no . . . C(12) C(13) H(13A) 107.920 no . . . C(12) C(13) H(13B) 107.920 no . . . C(14) C(13) H(13A) 107.909 no . . . C(14) C(13) H(13B) 107.910 no . . . H(13A) C(13) H(13B) 107.202 no . . . C(8) C(14) H(14A) 108.363 no . . . C(8) C(14) H(14B) 108.364 no . . . C(13) C(14) H(14A) 108.375 no . . . C(13) C(14) H(14B) 108.373 no . . . H(14A) C(14) H(14B) 107.434 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(6) N(1) C(7) O(2) 169.2(5) no . . . . C(6) N(1) C(7) C(4) -10.4(8) no . . . . C(7) N(1) C(6) O(1) -171.3(5) no . . . . C(7) N(1) C(6) C(2) 7.4(8) no . . . . C(6) N(1) C(8) C(9) 132.6(5) no . . . . C(6) N(1) C(8) C(14) -96.4(6) no . . . . C(8) N(1) C(6) O(1) 5.4(8) no . . . . C(8) N(1) C(6) C(2) -175.9(5) no . . . . C(7) N(1) C(8) C(9) -50.5(7) no . . . . C(7) N(1) C(8) C(14) 80.4(6) no . . . . C(8) N(1) C(7) O(2) -7.5(8) no . . . . C(8) N(1) C(7) C(4) 172.9(4) no . . . . C(2) C(1) C(5) C(4) -0.2(9) no . . 2_666 2_666 C(5) C(1) C(2) C(3) -0.6(9) no 2_666 . . . C(5) C(1) C(2) C(6) -175.3(5) no 2_666 . . . C(1) C(2) C(3) C(3) 3.0(8) no . . . 2_666 C(1) C(2) C(3) C(4) 178.2(5) no . . . . C(1) C(2) C(6) O(1) -5.0(9) no . . . . C(1) C(2) C(6) N(1) 176.3(5) no . . . . C(3) C(2) C(6) O(1) -179.8(5) no . . . . C(3) C(2) C(6) N(1) 1.5(8) no . . . . C(6) C(2) C(3) C(3) 178.0(5) no . . . 2_666 C(6) C(2) C(3) C(4) -6.8(8) no . . . . C(2) C(3) C(3) C(2) 180(799224) no . . 2_666 2_666 C(2) C(3) C(3) C(4) -4.8(8) no . . 2_666 2_666 C(2) C(3) C(4) C(5) -179.1(5) no . . . . C(2) C(3) C(4) C(7) 3.7(8) no . . . . C(3) C(3) C(4) C(5) -4.1(8) no 2_666 . . . C(3) C(3) C(4) C(7) 178.7(5) no 2_666 . . . C(4) C(3) C(3) C(2) 4.8(8) no . . 2_666 2_666 C(4) C(3) C(3) C(4) 180(569358) no . . 2_666 2_666 C(3) C(4) C(5) C(1) 1.5(8) no . . . 2_666 C(3) C(4) C(7) O(2) -174.8(5) no . . . . C(3) C(4) C(7) N(1) 4.8(8) no . . . . C(5) C(4) C(7) O(2) 8.0(9) no . . . . C(5) C(4) C(7) N(1) -172.4(5) no . . . . C(7) C(4) C(5) C(1) 178.8(5) no . . . 2_666 N(1) C(8) C(9) C(10) -148.0(5) no . . . . N(1) C(8) C(14) C(13) -167.0(5) no . . . . C(9) C(8) C(14) C(13) -38.2(9) no . . . . C(14) C(8) C(9) C(10) 85.4(7) no . . . . C(8) C(9) C(10) C(11) -72.8(7) no . . . . C(9) C(10) C(11) C(12) 56.2(9) no . . . . C(10) C(11) C(12) C(13) -71.1(8) no . . . . C(11) C(12) C(13) C(14) 85.0(8) no . . . . C(12) C(13) C(14) C(8) -38.2(9) no . . . . 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) C(1) 2.818(9) no . . O(1) C(3) 3.591(9) no . . O(1) C(7) 3.561(9) no . . O(1) C(8) 2.744(8) no . . O(1) C(14) 3.435(10) no . . O(2) C(3) 3.596(8) no . . O(2) C(5) 2.815(9) no . . O(2) C(6) 3.536(9) no . . O(2) C(8) 2.747(9) no . . O(2) C(9) 2.818(9) no . . O(2) C(14) 3.143(10) no . . N(1) C(3) 2.810(9) no . . C(1) C(3) 2.754(10) no . 2_666 C(2) C(4) 2.798(10) no . 2_666 C(2) C(7) 2.887(10) no . . C(3) C(5) 2.780(9) no . 2_666 C(4) C(6) 2.819(10) no . . C(6) C(14) 3.320(11) no . . C(7) C(9) 2.980(10) no . . C(7) C(14) 3.168(11) no . . C(8) C(11) 3.220(10) no . . C(8) C(12) 3.013(11) no . . C(9) C(12) 3.106(11) no . . C(9) C(13) 3.005(10) no . . C(10) C(13) 3.203(10) no . . C(10) C(14) 3.370(10) no . . C(11) C(14) 3.383(11) no . . O(1) O(2) 3.377(7) no . 1_556 O(1) C(1) 3.326(9) no . 2_567 O(1) C(4) 3.529(8) no . 1_556 O(1) C(5) 3.475(10) no . 1_456 O(1) C(7) 3.345(8) no . 1_556 O(2) O(1) 3.377(7) no . 1_554 O(2) C(6) 3.562(8) no . 1_554 O(2) C(8) 3.402(9) no . 1_554 O(2) C(9) 3.351(9) no . 1_554 O(2) C(10) 3.321(9) no . 1_554 O(2) C(14) 3.466(9) no . 1_655 C(1) O(1) 3.326(9) no . 2_567 C(1) C(1) 3.531(9) no . 2_667 C(1) C(2) 3.598(9) no . 2_667 C(2) C(1) 3.598(9) no . 2_667 C(2) C(5) 3.396(9) no . 1_556 C(4) O(1) 3.529(8) no . 1_554 C(5) O(1) 3.475(10) no . 1_654 C(5) C(2) 3.396(9) no . 1_554 C(5) C(6) 3.532(9) no . 1_554 C(6) O(2) 3.562(8) no . 1_556 C(6) C(5) 3.532(9) no . 1_556 C(7) O(1) 3.345(8) no . 1_554 C(8) O(2) 3.402(9) no . 1_556 C(9) O(2) 3.351(9) no . 1_556 C(10) O(2) 3.321(9) no . 1_556 C(14) O(2) 3.466(9) no . 1_455 O(1) H(1) 2.5368 no . . O(1) H(8) 2.3028 no . . O(1) H(14B) 3.0453 no . . O(2) H(2) 2.5378 no . . O(2) H(9A) 2.4728 no . . O(2) H(9B) 2.7877 no . . O(2) H(14A) 2.5979 no . . N(1) H(9A) 2.9435 no . . N(1) H(9B) 2.5212 no . . N(1) H(14A) 2.5215 no . . N(1) H(14B) 2.7137 no . . C(2) H(2) 3.2192 no . 2_666 C(3) H(1) 3.2236 no . . C(3) H(2) 3.2290 no . . C(4) H(1) 3.2264 no . 2_666 C(6) H(1) 2.6237 no . . C(6) H(8) 2.4829 no . . C(6) H(9B) 3.5771 no . . C(6) H(14A) 3.5127 no . . C(6) H(14B) 3.1770 no . . C(7) H(2) 2.6052 no . . C(7) H(8) 3.2619 no . . C(7) H(9A) 3.0235 no . . C(7) H(9B) 2.8063 no . . C(7) H(14A) 2.8019 no . . C(8) H(10A) 2.6406 no . . C(8) H(10B) 3.3387 no . . C(8) H(12A) 2.8861 no . . C(8) H(13A) 2.9395 no . . C(8) H(13B) 3.3618 no . . C(9) H(11A) 2.7999 no . . C(9) H(11B) 3.3778 no . . C(9) H(12A) 3.2580 no . . C(9) H(13A) 2.9773 no . . C(9) H(14A) 2.9559 no . . C(9) H(14B) 3.3698 no . . C(10) H(8) 2.5091 no . . C(10) H(12A) 2.6984 no . . C(10) H(12B) 3.3680 no . . C(10) H(13A) 3.2632 no . . C(11) H(8) 3.2055 no . . C(11) H(9A) 2.6956 no . . C(11) H(9B) 3.3683 no . . C(11) H(13A) 2.5719 no . . C(11) H(13B) 3.3131 no . . C(12) H(8) 2.9171 no . . C(12) H(9A) 3.2425 no . . C(12) H(10A) 2.7916 no . . C(12) H(10B) 3.3770 no . . C(12) H(14A) 3.3622 no . . C(12) H(14B) 2.9536 no . . C(13) H(8) 2.8874 no . . C(13) H(9A) 2.8684 no . . C(13) H(11A) 2.6682 no . . C(13) H(11B) 3.3458 no . . C(14) H(9A) 2.6506 no . . C(14) H(9B) 3.3593 no . . C(14) H(12A) 2.6511 no . . C(14) H(12B) 3.3527 no . . H(1) H(2) 2.2927 no . 2_666 H(8) H(9A) 2.7747 no . . H(8) H(9B) 2.4739 no . . H(8) H(10A) 2.2544 no . . H(8) H(10B) 3.3754 no . . H(8) H(12A) 2.4895 no . . H(8) H(13A) 3.4543 no . . H(8) H(13B) 3.5963 no . . H(8) H(14A) 2.7875 no . . H(8) H(14B) 2.2073 no . . H(9A) H(10A) 2.8198 no . . H(9A) H(10B) 2.4091 no . . H(9A) H(11A) 2.5844 no . . H(9A) H(11B) 3.5875 no . . H(9A) H(13A) 2.5397 no . . H(9A) H(14A) 2.7597 no . . H(9A) H(14B) 3.5704 no . . H(9B) H(10A) 2.4026 no . . H(9B) H(10B) 2.2518 no . . H(9B) H(11A) 3.5859 no . . H(10A) H(11A) 2.8090 no . . H(10A) H(11B) 2.2947 no . . H(10A) H(12A) 2.5793 no . . H(10A) H(12B) 3.5862 no . . H(10B) H(11A) 2.2963 no . . H(10B) H(11B) 2.3170 no . . H(10B) H(12A) 3.5879 no . . H(11A) H(12A) 2.8280 no . . H(11A) H(12B) 2.4023 no . . H(11A) H(13A) 2.3383 no . . H(11A) H(13B) 3.4110 no . . H(11B) H(12A) 2.4052 no . . H(11B) H(12B) 2.2684 no . . H(11B) H(13A) 3.4343 no . . H(12A) H(13A) 2.7834 no . . H(12A) H(13B) 2.4578 no . . H(12A) H(14A) 3.5687 no . . H(12A) H(14B) 2.7595 no . . H(12B) H(13A) 2.4487 no . . H(12B) H(13B) 2.1725 no . . H(13A) H(14A) 2.2094 no . . H(13A) H(14B) 2.7844 no . . H(13B) H(14A) 2.4208 no . . H(13B) H(14B) 2.2126 no . . O(1) H(1) 2.6169 no . 2_567 O(1) H(2) 2.9350 no . 1_456 O(1) H(14A) 3.2602 no . 1_556 O(2) H(8) 2.8359 no . 1_554 O(2) H(9B) 2.9794 no . 1_554 O(2) H(10A) 2.6181 no . 1_554 O(2) H(10B) 3.5818 no . 1_554 O(2) H(13B) 2.9731 no . 1_655 O(2) H(14B) 2.6890 no . 1_655 N(1) H(2) 3.5969 no . 1_556 C(1) H(1) 3.1489 no . 2_567 C(2) H(2) 3.4847 no . 1_556 C(3) H(1) 3.5198 no . 1_554 C(3) H(1) 3.5738 no . 2_667 C(4) H(14B) 3.2718 no . 1_655 C(5) H(14B) 3.0077 no . 1_655 C(6) H(1) 3.5534 no . 2_567 C(6) H(2) 3.4223 no . 1_556 C(7) H(8) 3.5641 no . 1_554 C(7) H(14B) 3.0349 no . 1_655 C(8) H(14A) 3.5721 no . 1_556 C(9) H(10A) 3.4585 no . 1_554 C(9) H(12A) 3.2199 no . 1_655 C(9) H(12B) 3.4795 no . 1_655 C(9) H(13B) 3.4909 no . 1_655 C(10) H(9A) 3.4060 no . 1_556 C(10) H(11B) 3.5059 no . 2_677 C(10) H(13A) 3.2627 no . 1_556 C(10) H(13B) 3.2550 no . 1_656 C(10) H(14A) 3.5789 no . 1_556 C(11) H(10B) 3.1470 no . 2_677 C(11) H(11B) 3.5430 no . 2_577 C(11) H(12B) 3.3761 no . 2_576 C(11) H(13A) 3.2033 no . 1_556 C(12) H(9A) 3.4104 no . 1_455 C(12) H(9B) 3.2454 no . 1_455 C(12) H(10B) 3.4654 no . 1_455 C(12) H(11A) 3.3710 no . 2_576 C(12) H(11B) 3.3082 no . 2_577 C(12) H(13A) 3.3361 no . 1_556 C(13) H(9A) 3.4791 no . 1_455 C(13) H(9B) 3.5568 no . 1_455 C(13) H(10A) 3.3010 no . 1_554 C(13) H(10B) 3.5288 no . 1_454 C(13) H(11A) 3.5361 no . 2_576 C(13) H(12A) 3.2211 no . 1_554 C(14) H(2) 3.2109 no . 1_455 C(14) H(8) 3.5631 no . 1_554 C(14) H(10A) 3.2889 no . 1_554 H(1) O(1) 2.6169 no . 2_567 H(1) C(1) 3.1489 no . 2_567 H(1) C(3) 3.5198 no . 1_556 H(1) C(3) 3.5738 no . 2_667 H(1) C(6) 3.5534 no . 2_567 H(1) H(1) 2.2497 no . 2_567 H(2) O(1) 2.9350 no . 1_654 H(2) N(1) 3.5969 no . 1_554 H(2) C(2) 3.4847 no . 1_554 H(2) C(6) 3.4223 no . 1_554 H(2) C(14) 3.2109 no . 1_655 H(2) H(9B) 3.4760 no . 1_554 H(2) H(14A) 2.9445 no . 1_655 H(2) H(14B) 2.5723 no . 1_655 H(8) O(2) 2.8359 no . 1_556 H(8) C(7) 3.5641 no . 1_556 H(8) C(14) 3.5631 no . 1_556 H(8) H(14A) 2.6055 no . 1_556 H(9A) C(10) 3.4060 no . 1_554 H(9A) C(12) 3.4104 no . 1_655 H(9A) C(13) 3.4791 no . 1_655 H(9A) H(10A) 2.5721 no . 1_554 H(9A) H(10B) 3.3981 no . 1_554 H(9A) H(12A) 3.1624 no . 1_655 H(9A) H(12B) 3.0748 no . 1_655 H(9A) H(13B) 2.8168 no . 1_655 H(9B) O(2) 2.9794 no . 1_556 H(9B) C(12) 3.2454 no . 1_655 H(9B) C(13) 3.5568 no . 1_655 H(9B) H(2) 3.4760 no . 1_556 H(9B) H(12A) 2.5835 no . 1_655 H(9B) H(12B) 3.2541 no . 1_655 H(9B) H(13B) 3.2554 no . 1_655 H(9B) H(13B) 3.2203 no . 1_656 H(9B) H(14B) 3.1790 no . 1_655 H(10A) O(2) 2.6181 no . 1_556 H(10A) C(9) 3.4585 no . 1_556 H(10A) C(13) 3.3010 no . 1_556 H(10A) C(14) 3.2889 no . 1_556 H(10A) H(9A) 2.5721 no . 1_556 H(10A) H(13A) 2.5327 no . 1_556 H(10A) H(13B) 3.0838 no . 1_656 H(10A) H(14A) 2.6898 no . 1_556 H(10B) O(2) 3.5818 no . 1_556 H(10B) C(11) 3.1470 no . 2_677 H(10B) C(12) 3.4654 no . 1_655 H(10B) C(13) 3.5288 no . 1_656 H(10B) H(9A) 3.3981 no . 1_556 H(10B) H(10B) 3.2188 no . 2_677 H(10B) H(11A) 2.8984 no . 2_677 H(10B) H(11B) 2.5943 no . 2_677 H(10B) H(12A) 3.0142 no . 1_655 H(10B) H(12B) 2.9812 no . 1_655 H(10B) H(13B) 2.6436 no . 1_656 H(11A) C(12) 3.3710 no . 2_576 H(11A) C(13) 3.5361 no . 2_576 H(11A) H(10B) 2.8984 no . 2_677 H(11A) H(12B) 2.5859 no . 2_576 H(11A) H(13A) 3.4090 no . 2_576 H(11A) H(13B) 3.1771 no . 2_576 H(11B) C(10) 3.5059 no . 2_677 H(11B) C(11) 3.5430 no . 2_577 H(11B) C(12) 3.3082 no . 2_577 H(11B) H(10B) 2.5943 no . 2_677 H(11B) H(11B) 2.8880 no . 2_577 H(11B) H(12A) 3.3578 no . 2_577 H(11B) H(12B) 2.6511 no . 2_577 H(11B) H(13A) 2.7651 no . 1_556 H(11B) H(13A) 3.3353 no . 2_576 H(11B) H(13B) 3.4048 no . 2_576 H(12A) C(9) 3.2199 no . 1_455 H(12A) C(13) 3.2211 no . 1_556 H(12A) H(9A) 3.1624 no . 1_455 H(12A) H(9B) 2.5835 no . 1_455 H(12A) H(10B) 3.0142 no . 1_455 H(12A) H(11B) 3.3578 no . 2_577 H(12A) H(13A) 2.7138 no . 1_556 H(12A) H(13B) 2.9733 no . 1_556 H(12A) H(14A) 3.0407 no . 1_556 H(12B) C(9) 3.4795 no . 1_455 H(12B) C(11) 3.3761 no . 2_576 H(12B) H(9A) 3.0748 no . 1_455 H(12B) H(9B) 3.2541 no . 1_455 H(12B) H(10B) 2.9812 no . 1_455 H(12B) H(11A) 2.5859 no . 2_576 H(12B) H(11B) 2.6511 no . 2_577 H(12B) H(12B) 3.2874 no . 2_576 H(12B) H(13A) 3.0728 no . 2_576 H(13A) C(10) 3.2627 no . 1_554 H(13A) C(11) 3.2033 no . 1_554 H(13A) C(12) 3.3361 no . 1_554 H(13A) H(10A) 2.5327 no . 1_554 H(13A) H(11A) 3.4090 no . 2_576 H(13A) H(11B) 2.7651 no . 1_554 H(13A) H(11B) 3.3353 no . 2_576 H(13A) H(12A) 2.7138 no . 1_554 H(13A) H(12B) 3.0728 no . 2_576 H(13B) O(2) 2.9731 no . 1_455 H(13B) C(9) 3.4909 no . 1_455 H(13B) C(10) 3.2550 no . 1_454 H(13B) H(9A) 2.8168 no . 1_455 H(13B) H(9B) 3.2203 no . 1_454 H(13B) H(9B) 3.2554 no . 1_455 H(13B) H(10A) 3.0838 no . 1_454 H(13B) H(10B) 2.6436 no . 1_454 H(13B) H(11A) 3.1771 no . 2_576 H(13B) H(11B) 3.4048 no . 2_576 H(13B) H(12A) 2.9733 no . 1_554 H(14A) O(1) 3.2602 no . 1_554 H(14A) C(8) 3.5721 no . 1_554 H(14A) C(10) 3.5789 no . 1_554 H(14A) H(2) 2.9445 no . 1_455 H(14A) H(8) 2.6055 no . 1_554 H(14A) H(10A) 2.6898 no . 1_554 H(14A) H(12A) 3.0407 no . 1_554 H(14B) O(2) 2.6890 no . 1_455 H(14B) C(4) 3.2718 no . 1_455 H(14B) C(5) 3.0077 no . 1_455 H(14B) C(7) 3.0349 no . 1_455 H(14B) H(2) 2.5723 no . 1_455 H(14B) H(9B) 3.1790 no . 1_455 #============================================================================== #============================================================================== # 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 #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 939279' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Cytidine_(Rigaku_Master_fo #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C30 H34 N2 O4' _chemical_formula_moiety 'C30 H34 N2 O4' _chemical_formula_weight 486.61 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 19.385(4) _cell_length_b 7.095(3) _cell_length_c 8.960(4) _cell_angle_alpha 90.0000 _cell_angle_beta 97.38(2) _cell_angle_gamma 90.0000 _cell_volume 1222.2(7) _cell_formula_units_Z 2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15.12 _cell_measurement_theta_max 17.32 _cell_measurement_temperature 298 #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520.00 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.849 _exptl_absorpt_correction_T_max 0.983 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 298 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 8076 _diffrn_reflns_av_R_equivalents 0.1377 _diffrn_reflns_theta_max 30.08 _diffrn_reflns_theta_full 30.08 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 6 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -0.856 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3575 _reflns_number_gt 1445 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0669 _refine_ls_wR_factor_ref 0.2591 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 3575 _refine_ls_number_parameters 163 _refine_ls_goodness_of_fit_ref 0.979 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1271P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.320 _refine_diff_density_min -0.310 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; 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 O1 O 0.28557(11) -0.0102(4) 0.5116(3) 0.0508(7) Uani 1.0 4 d . . . O17 O 0.38177(12) 0.0618(4) 0.0774(3) 0.0544(7) Uani 1.0 4 d . . . N4 N 0.33209(12) 0.0433(4) 0.2944(3) 0.0387(6) Uani 1.0 4 d . . . C2 C 0.40765(15) -0.0094(4) 0.5347(3) 0.0347(6) Uani 1.0 4 d . . . C3 C 0.45937(15) 0.0357(4) 0.3012(3) 0.0355(6) Uani 1.0 4 d . . . C5 C 0.38953(16) 0.0479(5) 0.2142(3) 0.0398(7) Uani 1.0 4 d . . . C6 C 0.33714(15) 0.0077(5) 0.4493(4) 0.0392(7) Uani 1.0 4 d . . . C7 C 0.41566(16) -0.0390(5) 0.6884(3) 0.0421(7) Uani 1.0 4 d . . . C8 C 0.51773(15) 0.0506(5) 0.2293(3) 0.0398(7) Uani 1.0 4 d . . . C9 C 0.26111(14) 0.0678(5) 0.2080(3) 0.0401(7) Uani 1.0 4 d . . . C10 C 0.22490(14) 0.2364(5) 0.2689(4) 0.0426(7) Uani 1.0 4 d . . . C11 C 0.22424(17) -0.1229(5) 0.1940(4) 0.0497(8) Uani 1.0 4 d . . . C12 C 0.09005(16) 0.2367(6) 0.2206(4) 0.0563(9) Uani 1.0 4 d . . . C13 C 0.15868(16) 0.3022(5) 0.1722(4) 0.0510(8) Uani 1.0 4 d . . . C14 C 0.08503(18) 0.0331(6) 0.2675(5) 0.0592(10) Uani 1.0 4 d . . . C15 C 0.15790(18) -0.1302(6) 0.0813(4) 0.0574(10) Uani 1.0 4 d . . . C16 C 0.09007(19) -0.1174(6) 0.1475(5) 0.0709(11) Uani 1.0 4 d . . . C18 C 0.46662(14) 0.0067(4) 0.4588(3) 0.0333(6) Uani 1.0 4 d . . . H7 H 0.3766 -0.0513 0.7378 0.0505 Uiso 1.0 4 calc R . . H8 H 0.5131 0.0685 0.1257 0.0478 Uiso 1.0 4 calc R . . H9 H 0.2689 0.1024 0.1056 0.0482 Uiso 1.0 4 calc R . . H10A H 0.2574 0.3409 0.2807 0.0511 Uiso 1.0 4 calc R . . H10B H 0.2134 0.2047 0.3681 0.0511 Uiso 1.0 4 calc R . . H11A H 0.2126 -0.1583 0.2923 0.0597 Uiso 1.0 4 calc R . . H11B H 0.2565 -0.2164 0.1650 0.0597 Uiso 1.0 4 calc R . . H12A H 0.0803 0.3152 0.3040 0.0675 Uiso 1.0 4 calc R . . H12B H 0.0536 0.2599 0.1379 0.0675 Uiso 1.0 4 calc R . . H13A H 0.1587 0.4389 0.1707 0.0612 Uiso 1.0 4 calc R . . H13B H 0.1605 0.2595 0.0700 0.0612 Uiso 1.0 4 calc R . . H14A H 0.0411 0.0164 0.3067 0.0710 Uiso 1.0 4 calc R . . H14B H 0.1217 0.0096 0.3497 0.0710 Uiso 1.0 4 calc R . . H15A H 0.1594 -0.0277 0.0102 0.0689 Uiso 1.0 4 calc R . . H15B H 0.1580 -0.2471 0.0252 0.0689 Uiso 1.0 4 calc R . . H16A H 0.0813 -0.2390 0.1908 0.0851 Uiso 1.0 4 calc R . . H16B H 0.0531 -0.0950 0.0657 0.0851 Uiso 1.0 4 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0398(13) 0.0703(16) 0.0435(12) 0.0024(11) 0.0100(9) 0.0095(11) O17 0.0548(14) 0.0781(17) 0.0307(11) 0.0034(12) 0.0064(9) 0.0047(11) N4 0.0387(13) 0.0467(15) 0.0307(11) 0.0040(11) 0.0053(10) 0.0026(11) C2 0.0369(15) 0.0349(15) 0.0334(13) 0.0001(11) 0.0085(11) 0.0022(11) C3 0.0385(15) 0.0366(14) 0.0320(13) 0.0011(12) 0.0074(11) 0.0020(12) C5 0.0457(17) 0.0416(16) 0.0330(14) 0.0030(14) 0.0081(12) 0.0015(13) C6 0.0401(16) 0.0423(16) 0.0369(14) 0.0050(12) 0.0114(12) 0.0044(12) C7 0.0404(17) 0.0518(19) 0.0362(14) 0.0011(14) 0.0136(12) 0.0037(13) C8 0.0419(17) 0.0495(18) 0.0295(14) -0.0001(14) 0.0102(12) 0.0033(13) C9 0.0325(15) 0.0535(18) 0.0336(13) 0.0044(13) 0.0010(11) 0.0037(14) C10 0.0425(16) 0.0388(16) 0.0462(16) 0.0014(13) 0.0050(13) 0.0008(13) C11 0.0508(19) 0.0444(18) 0.0520(18) 0.0032(15) -0.0007(14) -0.0095(15) C12 0.0430(18) 0.069(3) 0.056(2) 0.0115(17) 0.0040(15) -0.0019(18) C13 0.0553(19) 0.0493(19) 0.0484(18) 0.0129(15) 0.0068(14) 0.0083(15) C14 0.0421(19) 0.069(3) 0.068(3) -0.0060(17) 0.0150(17) -0.0009(19) C15 0.060(3) 0.059(3) 0.0506(19) 0.0008(17) -0.0033(16) -0.0158(17) C16 0.053(3) 0.073(3) 0.083(3) -0.0071(19) -0.0078(19) -0.013(3) C18 0.0373(15) 0.0324(14) 0.0315(13) 0.0015(11) 0.0093(11) 0.0014(11) #============================================================================== _computing_data_collection WinAFC _computing_cell_refinement WinAFC _computing_data_reduction WinAFC _computing_structure_solution 'Il Milione (Burla, et al., 2007)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # 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 O1 C6 1.213(4) yes . . O17 C5 1.220(4) yes . . N4 C5 1.401(4) yes . . N4 C6 1.401(4) yes . . N4 C9 1.500(4) yes . . C2 C6 1.483(4) yes . . C2 C7 1.382(4) yes . . C2 C18 1.408(5) yes . . C3 C5 1.475(4) yes . . C3 C8 1.376(5) yes . . C3 C18 1.416(4) yes . . C7 C8 1.405(4) yes . 3_656 C9 C10 1.524(5) yes . . C9 C11 1.528(5) yes . . C10 C13 1.526(4) yes . . C11 C15 1.531(5) yes . . C12 C13 1.523(5) yes . . C12 C14 1.512(6) yes . . C14 C16 1.527(6) yes . . C15 C16 1.513(6) yes . . C18 C18 1.408(4) yes . 3_656 C7 H7 0.930 no . . C8 H8 0.930 no . . C9 H9 0.980 no . . C10 H10A 0.970 no . . C10 H10B 0.970 no . . C11 H11A 0.970 no . . C11 H11B 0.970 no . . C12 H12A 0.970 no . . C12 H12B 0.970 no . . C13 H13A 0.970 no . . C13 H13B 0.970 no . . C14 H14A 0.970 no . . C14 H14B 0.970 no . . C15 H15A 0.970 no . . C15 H15B 0.970 no . . C16 H16A 0.970 no . . C16 H16B 0.970 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 C5 N4 C6 123.6(3) yes . . . C5 N4 C9 118.0(3) yes . . . C6 N4 C9 118.4(3) yes . . . C6 C2 C7 120.3(3) yes . . . C6 C2 C18 119.8(3) yes . . . C7 C2 C18 119.9(3) yes . . . C5 C3 C8 120.1(3) yes . . . C5 C3 C18 120.1(3) yes . . . C8 C3 C18 119.7(3) yes . . . O17 C5 N4 120.9(3) yes . . . O17 C5 C3 121.5(3) yes . . . N4 C5 C3 117.6(3) yes . . . O1 C6 N4 121.2(3) yes . . . O1 C6 C2 120.9(3) yes . . . N4 C6 C2 117.9(3) yes . . . C2 C7 C8 120.7(3) yes . . 3_656 C3 C8 C7 120.3(3) yes . . 3_656 N4 C9 C10 109.9(3) yes . . . N4 C9 C11 109.2(3) yes . . . C10 C9 C11 119.5(3) yes . . . C9 C10 C13 115.4(3) yes . . . C9 C11 C15 115.4(3) yes . . . C13 C12 C14 117.4(3) yes . . . C10 C13 C12 116.6(3) yes . . . C12 C14 C16 117.4(4) yes . . . C11 C15 C16 116.0(3) yes . . . C14 C16 C15 117.1(4) yes . . . C2 C18 C3 120.7(3) yes . . . C2 C18 C18 119.4(3) yes . . 3_656 C3 C18 C18 119.9(3) yes . . 3_656 C2 C7 H7 119.657 no . . . C8 C7 H7 119.658 no 3_656 . . C3 C8 H8 119.840 no . . . C7 C8 H8 119.829 no 3_656 . . N4 C9 H9 105.755 no . . . C10 C9 H9 105.765 no . . . C11 C9 H9 105.765 no . . . C9 C10 H10A 108.424 no . . . C9 C10 H10B 108.423 no . . . C13 C10 H10A 108.414 no . . . C13 C10 H10B 108.417 no . . . H10A C10 H10B 107.466 no . . . C9 C11 H11A 108.430 no . . . C9 C11 H11B 108.421 no . . . C15 C11 H11A 108.435 no . . . C15 C11 H11B 108.438 no . . . H11A C11 H11B 107.473 no . . . C13 C12 H12A 107.948 no . . . C13 C12 H12B 107.946 no . . . C14 C12 H12A 107.951 no . . . C14 C12 H12B 107.955 no . . . H12A C12 H12B 107.231 no . . . C10 C13 H13A 108.151 no . . . C10 C13 H13B 108.149 no . . . C12 C13 H13A 108.150 no . . . C12 C13 H13B 108.151 no . . . H13A C13 H13B 107.326 no . . . C12 C14 H14A 107.959 no . . . C12 C14 H14B 107.955 no . . . C16 C14 H14A 107.956 no . . . C16 C14 H14B 107.951 no . . . H14A C14 H14B 107.224 no . . . C11 C15 H15A 108.291 no . . . C11 C15 H15B 108.286 no . . . C16 C15 H15A 108.286 no . . . C16 C15 H15B 108.281 no . . . H15A C15 H15B 107.393 no . . . C14 C16 H16A 108.023 no . . . C14 C16 H16B 108.023 no . . . C15 C16 H16A 108.031 no . . . C15 C16 H16B 108.022 no . . . H16A C16 H16B 107.257 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 C5 N4 C6 O1 -173.9(3) no . . . . C5 N4 C6 C2 5.5(4) no . . . . C6 N4 C5 O17 173.0(3) no . . . . C6 N4 C5 C3 -7.1(4) no . . . . C5 N4 C9 C10 -121.9(3) no . . . . C5 N4 C9 C11 105.2(3) no . . . . C9 N4 C5 O17 -3.7(4) no . . . . C9 N4 C5 C3 176.3(3) no . . . . C6 N4 C9 C10 61.3(3) no . . . . C6 N4 C9 C11 -71.6(3) no . . . . C9 N4 C6 O1 2.8(4) no . . . . C9 N4 C6 C2 -177.8(3) no . . . . C6 C2 C7 C8 -178.4(3) no . . . 3_656 C7 C2 C6 O1 -2.5(5) no . . . . C7 C2 C6 N4 178.1(3) no . . . . C6 C2 C18 C3 -1.1(4) no . . . . C6 C2 C18 C18 179.0(3) no . . . 3_656 C18 C2 C6 O1 178.2(3) no . . . . C18 C2 C6 N4 -1.2(4) no . . . . C7 C2 C18 C3 179.5(3) no . . . . C7 C2 C18 C18 -0.3(4) no . . . 3_656 C18 C2 C7 C8 0.9(5) no . . . 3_656 C5 C3 C8 C7 -180.0(3) no . . . 3_656 C8 C3 C5 O17 3.7(5) no . . . . C8 C3 C5 N4 -176.2(3) no . . . . C5 C3 C18 C2 -0.5(4) no . . . . C5 C3 C18 C18 179.4(3) no . . . 3_656 C18 C3 C5 O17 -175.6(3) no . . . . C18 C3 C5 N4 4.4(4) no . . . . C8 C3 C18 C2 -179.9(3) no . . . . C8 C3 C18 C18 0.0(4) no . . . 3_656 C18 C3 C8 C7 -0.6(4) no . . . 3_656 C2 C7 C8 C3 -1.0(5) no . . 3_656 3_656 N4 C9 C10 C13 168.2(2) no . . . . N4 C9 C11 C15 -167.6(3) no . . . . C10 C9 C11 C15 64.8(4) no . . . . C11 C9 C10 C13 -64.5(4) no . . . . C9 C10 C13 C12 99.2(3) no . . . . C9 C11 C15 C16 -100.5(4) no . . . . C13 C12 C14 C16 -64.8(4) no . . . . C14 C12 C13 C10 -43.5(4) no . . . . C12 C14 C16 C15 63.6(4) no . . . . C11 C15 C16 C14 45.2(5) no . . . . C2 C18 C18 C2 180(244641) no . . 3_656 3_656 C2 C18 C18 C3 -0.1(4) no . . 3_656 3_656 C3 C18 C18 C2 0.1(4) no . . 3_656 3_656 C3 C18 C18 C3 180(182076) no . . 3_656 3_656 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 O1 C5 3.565(4) no . . O1 C7 2.808(4) no . . O1 C9 2.757(4) no . . O1 C10 2.919(4) no . . O1 C11 3.047(4) no . . O17 C6 3.569(4) no . . O17 C8 2.808(4) no . . O17 C9 2.747(4) no . . O17 C11 3.599(5) no . . N4 C18 2.838(4) no . . C2 C3 2.805(4) no . 3_656 C2 C5 2.876(4) no . . C3 C6 2.867(5) no . . C5 C10 3.552(5) no . . C5 C11 3.409(5) no . . C6 C10 3.013(4) no . . C6 C11 3.097(5) no . . C7 C18 2.788(5) no . 3_656 C8 C18 2.802(4) no . 3_656 C9 C12 3.542(5) no . . C9 C14 3.530(5) no . . C9 C16 3.543(5) no . . C10 C14 3.070(5) no . . C10 C15 3.274(5) no . . C11 C13 3.269(5) no . . C11 C14 3.066(5) no . . C12 C15 3.238(6) no . . C13 C15 3.174(6) no . . C13 C16 3.256(6) no . . O1 C10 3.342(4) no . 4_555 O1 C11 3.370(5) no . 4_545 O1 C13 3.348(4) no . 4_555 O17 C2 3.245(4) no . 4_554 O17 C6 3.338(4) no . 4_554 O17 C7 3.566(5) no . 4_554 C2 O17 3.245(4) no . 4_555 C3 C8 3.485(5) no . 2_645 C5 C7 3.532(5) no . 4_554 C6 O17 3.338(4) no . 4_555 C7 O17 3.566(5) no . 4_555 C7 C5 3.532(5) no . 4_555 C8 C3 3.485(5) no . 2_655 C10 O1 3.342(4) no . 4_554 C11 O1 3.370(5) no . 4_544 C13 O1 3.348(4) no . 4_554 O1 H7 2.5270 no . . O1 H10A 3.2398 no . . O1 H10B 2.3393 no . . O1 H11A 2.5007 no . . O1 H11B 3.4139 no . . O1 H14B 3.3217 no . . O17 H8 2.5267 no . . O17 H9 2.2536 no . . O17 H11B 3.3004 no . . N4 H10A 2.5540 no . . N4 H10B 2.7253 no . . N4 H11A 2.7208 no . . N4 H11B 2.5394 no . . C2 H8 3.2559 no . 3_656 C3 H7 3.2461 no . 3_656 C5 H8 2.6217 no . . C5 H9 2.4461 no . . C5 H10A 3.4094 no . . C5 H11B 3.1728 no . . C6 H7 2.6335 no . . C6 H9 3.2620 no . . C6 H10A 3.1081 no . . C6 H10B 2.7902 no . . C6 H11A 2.8852 no . . C6 H11B 3.2306 no . . C9 H13A 3.2883 no . . C9 H13B 2.5628 no . . C9 H14B 3.1577 no . . C9 H15A 2.5664 no . . C9 H15B 3.2909 no . . C10 H11A 2.8213 no . . C10 H11B 3.4222 no . . C10 H12A 2.9150 no . . C10 H12B 3.3810 no . . C10 H14B 2.7370 no . . C10 H15A 3.1207 no . . C11 H10A 3.4231 no . . C11 H10B 2.8219 no . . C11 H13B 3.1264 no . . C11 H14B 2.7380 no . . C11 H16A 2.8878 no . . C11 H16B 3.3749 no . . C12 H10A 3.3039 no . . C12 H10B 2.5901 no . . C12 H15A 3.0874 no . . C12 H16A 3.3881 no . . C12 H16B 2.7789 no . . C13 H9 2.6939 no . . C13 H11A 3.5547 no . . C13 H14A 3.3862 no . . C13 H14B 2.7650 no . . C13 H15A 2.7551 no . . C13 H16B 3.5412 no . . C14 H10B 2.8134 no . . C14 H11A 2.8047 no . . C14 H13A 3.3768 no . . C14 H13B 2.9183 no . . C14 H15A 2.9043 no . . C14 H15B 3.3841 no . . C15 H9 2.6978 no . . C15 H10B 3.5633 no . . C15 H12B 3.5028 no . . C15 H13B 2.7677 no . . C15 H14A 3.3859 no . . C15 H14B 2.7741 no . . C16 H11A 2.5724 no . . C16 H11B 3.2865 no . . C16 H12A 3.3896 no . . C16 H12B 2.7673 no . . C16 H13B 3.1205 no . . C18 H7 3.2540 no . . C18 H8 3.2565 no . . H7 H8 2.3278 no . 3_656 H9 H10A 2.3373 no . . H9 H10B 2.8042 no . . H9 H11A 2.8073 no . . H9 H11B 2.3425 no . . H9 H13A 3.3043 no . . H9 H13B 2.3643 no . . H9 H15A 2.3698 no . . H9 H15B 3.3003 no . . H10A H12A 3.4720 no . . H10A H13A 2.1520 no . . H10A H13B 2.5534 no . . H10B H11A 2.6632 no . . H10B H12A 2.6883 no . . H10B H12B 3.5168 no . . H10B H13A 2.5561 no . . H10B H13B 2.7636 no . . H10B H14A 3.5752 no . . H10B H14B 2.2431 no . . H11A H14A 3.5664 no . . H11A H14B 2.2412 no . . H11A H15A 2.7642 no . . H11A H15B 2.5678 no . . H11A H16A 2.6532 no . . H11A H16B 3.5030 no . . H11B H15A 2.5665 no . . H11B H15B 2.1567 no . . H11B H16A 3.4386 no . . H12A H13A 2.2309 no . . H12A H13B 2.7938 no . . H12A H14A 2.2534 no . . H12A H14B 2.3298 no . . H12B H13A 2.3868 no . . H12B H13B 2.2323 no . . H12B H14A 2.3298 no . . H12B H14B 2.8030 no . . H12B H15A 3.2069 no . . H12B H16B 2.5996 no . . H13A H14B 3.5584 no . . H13B H14B 3.2368 no . . H13B H15A 2.1062 no . . H13B H16B 3.2619 no . . H14A H16A 2.2750 no . . H14A H16B 2.3385 no . . H14B H15A 3.2300 no . . H14B H15B 3.5768 no . . H14B H16A 2.3379 no . . H14B H16B 2.8152 no . . H15A H16A 2.7912 no . . H15A H16B 2.2339 no . . H15B H16A 2.2319 no . . H15B H16B 2.3709 no . . O1 H9 3.0426 no . 4_555 O1 H10A 2.8089 no . 4_555 O1 H11B 2.4831 no . 4_545 O1 H13A 3.0386 no . 4_555 O1 H13B 3.1059 no . 4_555 O1 H15B 3.0289 no . 4_545 O17 H7 3.1357 no . 1_554 O17 H8 3.0452 no . 3_655 O17 H10A 3.4221 no . 4_554 C3 H8 3.4077 no . 2_645 C5 H7 3.5409 no . 4_544 C5 H7 3.5883 no . 4_554 C6 H9 3.4414 no . 4_555 C6 H11B 3.3501 no . 4_545 C7 H10A 3.5663 no . 4_555 C7 H11B 3.5224 no . 4_545 C8 H8 3.2706 no . 3_655 C9 H10B 3.4659 no . 4_554 C10 H9 3.2364 no . 4_555 C10 H10B 3.5938 no . 4_554 C10 H13B 3.1152 no . 4_555 C10 H15A 3.3556 no . 4_555 C11 H13A 3.3548 no . 1_545 C11 H15B 3.5052 no . 4_545 C12 H13B 3.2507 no . 4_555 C12 H14A 3.2089 no . 2_555 C12 H15A 3.4510 no . 4_555 C12 H16A 3.5168 no . 2_555 C13 H10B 3.0495 no . 4_554 C13 H12A 3.5500 no . 4_554 C13 H13B 3.5861 no . 4_555 C13 H14B 3.1806 no . 4_554 C13 H15A 3.4232 no . 4_555 C13 H15B 3.4577 no . 1_565 C13 H16A 3.5976 no . 1_565 C14 H12A 3.5415 no . 2_545 C14 H12B 3.5046 no . 2_545 C14 H13B 3.2604 no . 4_555 C14 H15B 3.2571 no . 4_545 C15 H11A 3.2840 no . 4_544 C15 H12A 3.5319 no . 4_554 C15 H13A 3.1599 no . 1_545 C15 H14B 3.4161 no . 4_544 C16 H12A 3.4194 no . 2_545 C16 H13A 3.4142 no . 1_545 C16 H16B 3.5013 no . 3_555 C18 H8 3.2358 no . 2_645 C18 H8 3.4326 no . 4_555 H7 O17 3.1357 no . 1_556 H7 C5 3.5409 no . 4_545 H7 C5 3.5883 no . 4_555 H7 H10A 2.8170 no . 4_555 H7 H11B 2.8578 no . 4_545 H8 O17 3.0452 no . 3_655 H8 C3 3.4077 no . 2_655 H8 C8 3.2706 no . 3_655 H8 C18 3.2358 no . 2_655 H8 C18 3.4326 no . 4_554 H8 H8 2.4451 no . 3_655 H9 O1 3.0426 no . 4_554 H9 C6 3.4414 no . 4_554 H9 C10 3.2364 no . 4_554 H9 H10A 2.9191 no . 4_554 H9 H10B 2.6399 no . 4_554 H10A O1 2.8089 no . 4_554 H10A O17 3.4221 no . 4_555 H10A C7 3.5663 no . 4_554 H10A H7 2.8170 no . 4_554 H10A H9 2.9191 no . 4_555 H10A H11B 3.3072 no . 1_565 H10A H13B 3.4660 no . 4_555 H10A H15A 3.2556 no . 4_555 H10B C9 3.4659 no . 4_555 H10B C10 3.5938 no . 4_555 H10B C13 3.0495 no . 4_555 H10B H9 2.6399 no . 4_555 H10B H13A 3.2015 no . 4_555 H10B H13B 2.2065 no . 4_555 H10B H15A 2.8830 no . 4_555 H11A C15 3.2840 no . 4_545 H11A H11B 3.4546 no . 4_545 H11A H13A 3.1862 no . 1_545 H11A H15A 3.2175 no . 4_545 H11A H15B 2.5482 no . 4_545 H11B O1 2.4831 no . 4_544 H11B C6 3.3501 no . 4_544 H11B C7 3.5224 no . 4_544 H11B H7 2.8578 no . 4_544 H11B H10A 3.3072 no . 1_545 H11B H11A 3.4546 no . 4_544 H11B H13A 3.0992 no . 1_545 H12A C13 3.5500 no . 4_555 H12A C14 3.5415 no . 2_555 H12A C15 3.5319 no . 4_555 H12A C16 3.4194 no . 2_555 H12A H12B 3.1461 no . 4_555 H12A H13B 2.7247 no . 4_555 H12A H14A 2.8205 no . 2_555 H12A H15A 2.7044 no . 4_555 H12A H16A 3.3228 no . 1_565 H12A H16A 3.1615 no . 2_555 H12A H16B 3.0376 no . 2_555 H12A H16B 3.1682 no . 4_555 H12B C14 3.5046 no . 2_555 H12B H12A 3.1461 no . 4_554 H12B H14A 2.6757 no . 2_555 H12B H14A 3.3463 no . 4_554 H12B H14B 3.4575 no . 4_554 H12B H16A 3.1976 no . 2_555 H12B H16B 2.8295 no . 3_555 H13A O1 3.0386 no . 4_554 H13A C11 3.3548 no . 1_565 H13A C15 3.1599 no . 1_565 H13A C16 3.4142 no . 1_565 H13A H10B 3.2015 no . 4_554 H13A H11A 3.1862 no . 1_565 H13A H11B 3.0992 no . 1_565 H13A H14B 2.8960 no . 4_554 H13A H15A 3.1054 no . 4_555 H13A H15B 2.5800 no . 1_565 H13A H16A 2.7535 no . 1_565 H13B O1 3.1059 no . 4_554 H13B C10 3.1152 no . 4_554 H13B C12 3.2507 no . 4_554 H13B C13 3.5861 no . 4_554 H13B C14 3.2604 no . 4_554 H13B H10A 3.4660 no . 4_554 H13B H10B 2.2065 no . 4_554 H13B H12A 2.7247 no . 4_554 H13B H14A 3.4710 no . 4_554 H13B H14B 2.6002 no . 4_554 H13B H15B 3.5228 no . 1_565 H14A C12 3.2089 no . 2_545 H14A H12A 2.8205 no . 2_545 H14A H12B 2.6757 no . 2_545 H14A H12B 3.3463 no . 4_555 H14A H13B 3.4710 no . 4_555 H14A H15B 3.3882 no . 4_545 H14A H16A 2.9413 no . 2_555 H14A H16B 3.5743 no . 2_555 H14B C13 3.1806 no . 4_555 H14B C15 3.4161 no . 4_545 H14B H12B 3.4575 no . 4_555 H14B H13A 2.8960 no . 4_555 H14B H13B 2.6002 no . 4_555 H14B H15B 2.4801 no . 4_545 H15A C10 3.3556 no . 4_554 H15A C12 3.4510 no . 4_554 H15A C13 3.4232 no . 4_554 H15A H10A 3.2556 no . 4_554 H15A H10B 2.8830 no . 4_554 H15A H11A 3.2175 no . 4_544 H15A H12A 2.7044 no . 4_554 H15A H13A 3.1054 no . 4_554 H15A H16A 3.4807 no . 4_544 H15B O1 3.0289 no . 4_544 H15B C11 3.5052 no . 4_544 H15B C13 3.4577 no . 1_545 H15B C14 3.2571 no . 4_544 H15B H11A 2.5482 no . 4_544 H15B H13A 2.5800 no . 1_545 H15B H13B 3.5228 no . 1_545 H15B H14A 3.3882 no . 4_544 H15B H14B 2.4801 no . 4_544 H15B H16A 3.1710 no . 4_544 H16A C12 3.5168 no . 2_545 H16A C13 3.5976 no . 1_545 H16A H12A 3.3228 no . 1_545 H16A H12A 3.1615 no . 2_545 H16A H12B 3.1976 no . 2_545 H16A H13A 2.7535 no . 1_545 H16A H14A 2.9413 no . 2_545 H16A H15A 3.4807 no . 4_545 H16A H15B 3.1710 no . 4_545 H16B C16 3.5013 no . 3_555 H16B H12A 3.0376 no . 2_545 H16B H12A 3.1682 no . 4_554 H16B H12B 2.8295 no . 3_555 H16B H14A 3.5743 no . 2_545 H16B H16B 2.6111 no . 3_555 #============================================================================== #============================================================================== # 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 #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 939280'