data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Chopra, Deepak' _publ_contact_author_email dchopra@iiserbhopal.ac.in _publ_section_title ; Insights into conformational and packing features in a series of aryl substituted ethyl-6-methyl-4-phenyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates. ; loop_ _publ_author_name D.Chopra S.Nayak 'T.Guru Row' K.Venugopala # Attachment '- PYOX1.cif' # CIF-file generated for vsk12_m in P-1 #============================================================================== data_vsk12_m _database_code_depnum_ccdc_archive 'CCDC 761378' #TrackingRef '- PYOX1.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 F N2 O3' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C14 H14 F N2 O3' _chemical_formula_iupac ? _chemical_formula_weight 277.27 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M '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 7.5291(6) _cell_length_b 9.0289(7) _cell_length_c 11.2318(9) _cell_angle_alpha 106.417(1) _cell_angle_beta 104.611(1) _cell_angle_gamma 100.197(1) _cell_volume 682.88(9) _cell_formula_units_Z 2 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 430 _cell_measurement_theta_min 0.98 _cell_measurement_theta_max 27.98 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.23 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 290 _exptl_absorpt_coefficient_mu 0.105 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9672 _exptl_absorpt_correction_T_max 0.9763 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? # number of measured reflections (redundant set) _diffrn_reflns_number 6549 _diffrn_reflns_av_R_equivalents 0.0165 _diffrn_reflns_av_sigmaI/netI 0.0216 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 24.99 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 2399 # number of observed reflections (> n sig(I)) _reflns_number_gt 1963 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0760P)^2^+0.1309P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.056(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2399 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1389 _refine_ls_wR_factor_gt 0.1313 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.346 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.087 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT 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 F1 F 0.9092(3) 0.8199(2) 0.3411(2) 0.1028(9) Uani 0.842(4) 1 d P A 1 F1A F 0.6097(13) 0.3500(12) 0.3562(8) 0.080(4) Uani 0.158(4) 1 d P A 2 O1 O 0.73380(17) 0.13907(16) 0.05635(15) 0.0588(4) Uani 1 1 d . . . O2 O 0.15152(18) 0.54729(16) 0.15850(14) 0.0570(4) Uani 1 1 d . . . O3 O 0.43132(17) 0.72724(15) 0.21932(13) 0.0539(4) Uani 1 1 d . . . C3 C 0.4301(2) 0.4611(2) 0.14012(15) 0.0386(4) Uani 1 1 d . . . C4 C 0.6462(2) 0.5227(2) 0.18866(16) 0.0394(4) Uani 1 1 d . . . H4 H 0.6802 0.6147 0.1612 0.047 Uiso 1 1 calc R . . N2 N 0.72921(19) 0.39891(17) 0.12733(14) 0.0445(4) Uani 1 1 d . . . H2N H 0.8399 0.4301 0.1206 0.053 Uiso 1 1 calc R . . N1 N 0.4543(2) 0.19710(18) 0.05743(15) 0.0473(4) Uani 1 1 d . . . H1N H 0.3978 0.0964 0.0291 0.057 Uiso 1 1 calc R . . C2 C 0.3450(2) 0.3038(2) 0.07640(16) 0.0405(4) Uani 1 1 d . . . C5 C 0.3199(2) 0.5770(2) 0.17022(16) 0.0416(4) Uani 1 1 d . . . C1 C 0.6468(2) 0.2409(2) 0.08078(17) 0.0430(4) Uani 1 1 d . . . C9 C 0.7303(2) 0.5782(2) 0.33681(17) 0.0447(4) Uani 1 1 d . A . C6 C 0.3437(3) 0.8538(3) 0.2633(2) 0.0658(6) Uani 1 1 d . . . H6A H 0.2835 0.8339 0.3262 0.079 Uiso 1 1 calc R . . H6B H 0.2473 0.8585 0.1896 0.079 Uiso 1 1 calc R . . C8 C 0.1354(3) 0.2248(2) 0.0165(2) 0.0585(6) Uani 1 1 d . . . H8A H 0.0712 0.2987 -0.0099 0.088 Uiso 1 1 calc R . . H8B H 0.0876 0.1932 0.0797 0.088 Uiso 1 1 calc R . . H8C H 0.1133 0.1319 -0.0585 0.088 Uiso 1 1 calc R . . C10 C 0.8582(3) 0.7249(3) 0.4070(2) 0.0691(6) Uani 1 1 d . . . C14 C 0.6874(4) 0.4813(3) 0.4067(2) 0.0670(6) Uani 1 1 d . . . C13 C 0.7715(5) 0.5314(5) 0.5417(3) 0.0936(9) Uani 1 1 d . A . H13 H 0.7431 0.4637 0.5871 0.112 Uiso 1 1 calc R . . C12 C 0.8956(5) 0.6796(5) 0.6077(3) 0.1050(12) Uani 1 1 d . . . H12 H 0.9494 0.7137 0.6983 0.126 Uiso 1 1 calc R A . C7 C 0.4948(4) 1.0060(3) 0.3246(3) 0.0898(8) Uani 1 1 d . . . H7A H 0.5505 1.0263 0.2608 0.135 Uiso 1 1 calc R . . H7B H 0.5911 0.9990 0.3958 0.135 Uiso 1 1 calc R . . H7C H 0.4412 1.0918 0.3572 0.135 Uiso 1 1 calc R . . C11 C 0.9405(4) 0.7772(4) 0.5413(3) 0.1006(10) Uani 1 1 d . A . H11 H 1.0257 0.8781 0.5857 0.121 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0956(14) 0.0608(11) 0.1086(15) 0.0124(10) 0.0126(11) -0.0283(9) F1A 0.087(7) 0.080(7) 0.065(5) 0.038(5) 0.019(4) -0.005(5) O1 0.0358(7) 0.0457(7) 0.0877(10) 0.0087(7) 0.0240(7) 0.0106(6) O2 0.0366(7) 0.0573(8) 0.0744(9) 0.0175(7) 0.0168(6) 0.0159(6) O3 0.0420(7) 0.0428(7) 0.0680(9) 0.0113(6) 0.0105(6) 0.0125(6) C3 0.0316(9) 0.0444(9) 0.0386(9) 0.0158(7) 0.0091(7) 0.0082(7) C4 0.0328(9) 0.0377(9) 0.0464(10) 0.0147(7) 0.0126(7) 0.0058(7) N2 0.0286(7) 0.0456(9) 0.0550(9) 0.0111(7) 0.0167(6) 0.0045(6) N1 0.0311(8) 0.0378(8) 0.0659(10) 0.0096(7) 0.0165(7) 0.0044(6) C2 0.0313(9) 0.0450(10) 0.0439(9) 0.0151(8) 0.0116(7) 0.0079(7) C5 0.0357(10) 0.0459(10) 0.0402(9) 0.0153(7) 0.0074(7) 0.0099(7) C1 0.0333(9) 0.0430(10) 0.0492(10) 0.0107(8) 0.0155(7) 0.0070(8) C9 0.0318(9) 0.0492(10) 0.0482(10) 0.0116(8) 0.0087(7) 0.0135(7) C6 0.0594(13) 0.0525(12) 0.0765(14) 0.0099(10) 0.0142(11) 0.0238(10) C8 0.0321(10) 0.0528(11) 0.0751(14) 0.0076(10) 0.0116(9) 0.0055(8) C10 0.0519(12) 0.0604(13) 0.0681(14) 0.0018(11) 0.0030(10) 0.0063(10) C14 0.0749(15) 0.0767(17) 0.0534(13) 0.0274(12) 0.0190(11) 0.0237(13) C13 0.106(2) 0.139(3) 0.0569(15) 0.0463(17) 0.0286(15) 0.060(2) C12 0.095(2) 0.149(3) 0.0488(15) 0.0015(19) -0.0009(15) 0.066(2) C7 0.093(2) 0.0515(14) 0.111(2) 0.0119(13) 0.0281(16) 0.0166(13) C11 0.0745(18) 0.096(2) 0.0752(19) -0.0176(16) -0.0139(15) 0.0173(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C10 1.348(3) . ? F1A C14 1.130(9) . ? O1 C1 1.230(2) . ? O2 C5 1.213(2) . ? O3 C5 1.338(2) . ? O3 C6 1.448(2) . ? C3 C2 1.346(2) . ? C3 C5 1.465(2) . ? C3 C4 1.522(2) . ? C4 N2 1.464(2) . ? C4 C9 1.518(2) . ? C4 H4 0.9800 . ? N2 C1 1.339(2) . ? N2 H2N 0.8600 . ? N1 C1 1.368(2) . ? N1 C2 1.380(2) . ? N1 H1N 0.8600 . ? C2 C8 1.499(2) . ? C9 C10 1.371(3) . ? C9 C14 1.379(3) . ? C6 C7 1.474(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C10 C11 1.380(4) . ? C14 C13 1.390(3) . ? C13 C12 1.363(5) . ? C13 H13 0.9300 . ? C12 C11 1.357(5) . ? C12 H12 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C11 H11 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O3 C6 116.95(15) . . ? C2 C3 C5 121.62(15) . . ? C2 C3 C4 120.44(15) . . ? C5 C3 C4 117.88(15) . . ? N2 C4 C9 110.26(13) . . ? N2 C4 C3 109.87(13) . . ? C9 C4 C3 112.93(13) . . ? N2 C4 H4 107.9 . . ? C9 C4 H4 107.9 . . ? C3 C4 H4 107.9 . . ? C1 N2 C4 125.30(14) . . ? C1 N2 H2N 117.4 . . ? C4 N2 H2N 117.4 . . ? C1 N1 C2 124.30(15) . . ? C1 N1 H1N 117.9 . . ? C2 N1 H1N 117.9 . . ? C3 C2 N1 119.85(14) . . ? C3 C2 C8 127.20(16) . . ? N1 C2 C8 112.92(15) . . ? O2 C5 O3 121.95(16) . . ? O2 C5 C3 126.92(16) . . ? O3 C5 C3 111.08(14) . . ? O1 C1 N2 123.53(15) . . ? O1 C1 N1 120.71(16) . . ? N2 C1 N1 115.73(15) . . ? C10 C9 C14 116.8(2) . . ? C10 C9 C4 121.46(18) . . ? C14 C9 C4 121.72(18) . . ? O3 C6 C7 107.69(19) . . ? O3 C6 H6A 110.2 . . ? C7 C6 H6A 110.2 . . ? O3 C6 H6B 110.2 . . ? C7 C6 H6B 110.2 . . ? H6A C6 H6B 108.5 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? F1 C10 C9 118.3(2) . . ? F1 C10 C11 118.8(3) . . ? C9 C10 C11 122.8(3) . . ? F1A C14 C9 121.5(4) . . ? F1A C14 C13 116.1(5) . . ? C9 C14 C13 121.0(3) . . ? C12 C13 C14 120.2(3) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C11 C12 C13 120.0(3) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C12 C11 C10 119.2(3) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 C3 C4 N2 14.3(2) . . . . ? C5 C3 C4 N2 -168.41(14) . . . . ? C2 C3 C4 C9 -109.29(18) . . . . ? C5 C3 C4 C9 68.03(19) . . . . ? C9 C4 N2 C1 99.86(19) . . . . ? C3 C4 N2 C1 -25.2(2) . . . . ? C5 C3 C2 N1 -175.77(15) . . . . ? C4 C3 C2 N1 1.4(2) . . . . ? C5 C3 C2 C8 6.2(3) . . . . ? C4 C3 C2 C8 -176.60(17) . . . . ? C1 N1 C2 C3 -10.7(3) . . . . ? C1 N1 C2 C8 167.57(17) . . . . ? C6 O3 C5 O2 2.5(3) . . . . ? C6 O3 C5 C3 -175.20(15) . . . . ? C2 C3 C5 O2 9.9(3) . . . . ? C4 C3 C5 O2 -167.35(16) . . . . ? C2 C3 C5 O3 -172.51(15) . . . . ? C4 C3 C5 O3 10.2(2) . . . . ? C4 N2 C1 O1 -163.54(17) . . . . ? C4 N2 C1 N1 18.3(3) . . . . ? C2 N1 C1 O1 -176.89(16) . . . . ? C2 N1 C1 N2 1.3(3) . . . . ? N2 C4 C9 C10 106.8(2) . . . . ? C3 C4 C9 C10 -129.83(19) . . . . ? N2 C4 C9 C14 -70.7(2) . . . . ? C3 C4 C9 C14 52.7(2) . . . . ? C5 O3 C6 C7 174.64(19) . . . . ? C14 C9 C10 F1 177.4(2) . . . . ? C4 C9 C10 F1 -0.3(3) . . . . ? C14 C9 C10 C11 -0.8(3) . . . . ? C4 C9 C10 C11 -178.4(2) . . . . ? C10 C9 C14 F1A -166.6(6) . . . . ? C4 C9 C14 F1A 11.1(7) . . . . ? C10 C9 C14 C13 -0.2(3) . . . . ? C4 C9 C14 C13 177.4(2) . . . . ? F1A C14 C13 C12 168.4(6) . . . . ? C9 C14 C13 C12 1.4(4) . . . . ? C14 C13 C12 C11 -1.5(4) . . . . ? C13 C12 C11 C10 0.4(4) . . . . ? F1 C10 C11 C12 -177.4(3) . . . . ? C9 C10 C11 C12 0.7(4) . . . . ? #===END # Attachment '- PYOX2a.cif' # CIF-file generated for LT04FP in C2/c #============================================================================== data_lt04fp _database_code_depnum_ccdc_archive 'CCDC 761379' #TrackingRef '- PYOX2a.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H15 F N2 O3' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C14 H15 F N2 O3' _chemical_formula_iupac ? _chemical_formula_weight 278.28 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 2/c' _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 15.829(4) _cell_length_b 7.2551(12) _cell_length_c 24.285(4) _cell_angle_alpha 90 _cell_angle_beta 106.972(5) _cell_angle_gamma 90 _cell_volume 2667.4(9) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 401 _cell_measurement_theta_min 0.98 _cell_measurement_theta_max 27.98 _cell_special_details ; ; _exptl_crystal_description Plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.20 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.108 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.9644 _exptl_absorpt_correction_T_max 0.9788 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Goniometer Xcalibur, detector: Eos (Nova)' _diffrn_detector_area_resol_mean 16.0839 _diffrn_orient_matrix_UB_11 -0.0187237247 _diffrn_orient_matrix_UB_12 -0.0307237532 _diffrn_orient_matrix_UB_13 0.0282290082 _diffrn_orient_matrix_UB_21 -0.0859907631 _diffrn_orient_matrix_UB_22 -0.0092415542 _diffrn_orient_matrix_UB_23 -0.0075452043 _diffrn_orient_matrix_UB_31 0.0637226165 _diffrn_orient_matrix_UB_32 -0.0836934899 _diffrn_orient_matrix_UB_33 -0.0085524533 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -62.00 -2.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - -17.1989 104.0000 35.0000 60 #__ type_ start__ end____ width___ exp.time_ 2 omega -35.00 8.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - -17.1989 37.0000 -180.0000 43 #__ type_ start__ end____ width___ exp.time_ 3 omega 21.00 52.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - -17.1989 37.0000 -180.0000 31 #__ type_ start__ end____ width___ exp.time_ 4 omega -64.00 56.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - -17.1989 0.0000 0.0000 120 #__ type_ start__ end____ width___ exp.time_ 5 omega -11.00 89.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 77.0000 -120.0000 100 #__ type_ start__ end____ width___ exp.time_ 6 omega -11.00 89.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 77.0000 30.0000 100 #__ type_ start__ end____ width___ exp.time_ 7 omega 34.00 95.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 179.0000 150.0000 61 #__ type_ start__ end____ width___ exp.time_ 8 omega -17.00 63.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 -104.0000 -65.0000 80 #__ type_ start__ end____ width___ exp.time_ 9 omega -7.00 92.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 37.0000 -150.0000 99 #__ type_ start__ end____ width___ exp.time_ 10 omega 35.00 95.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 -179.0000 -78.0000 60 #__ type_ start__ end____ width___ exp.time_ 11 omega -90.00 -37.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - -17.1989 -37.0000 -120.0000 53 ; _diffrn_measurement_method '\w scans' # number of measured reflections (redundant set) _diffrn_reflns_number 18255 _diffrn_reflns_av_R_equivalents 0.0839 _diffrn_reflns_av_sigmaI/netI 0.0403 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 26.00 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 2619 # number of observed reflections (> n sig(I)) _reflns_number_gt 2136 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (2009) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0706P)^2^+3.1349P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2619 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0571 _refine_ls_wR_factor_ref 0.1427 _refine_ls_wR_factor_gt 0.1378 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.286 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.057 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT 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 0.76184(9) 0.4908(2) 0.99392(6) 0.0217(4) Uani 1 1 d . . . F1 F 0.91132(9) 0.6616(2) 1.30072(6) 0.0428(4) Uani 1 1 d . . . O3 O 0.48243(9) 0.7286(2) 1.10136(7) 0.0275(4) Uani 1 1 d . . . O2 O 0.44419(10) 0.4293(2) 1.09760(7) 0.0323(4) Uani 1 1 d . . . N1 N 0.67487(11) 0.3503(3) 1.04121(7) 0.0208(4) Uani 1 1 d . . . N2 N 0.68335(11) 0.6659(3) 1.03936(7) 0.0202(4) Uani 1 1 d . . . C4 C 0.64471(13) 0.6751(3) 1.08731(8) 0.0197(4) Uani 1 1 d . . . C10 C 0.70046(15) 0.5972(3) 1.19415(9) 0.0249(5) Uani 1 1 d . . . C3 C 0.57908(13) 0.5193(3) 1.07977(8) 0.0191(4) Uani 1 1 d . . . C14 C 0.79995(14) 0.7417(3) 1.15049(10) 0.0253(5) Uani 1 1 d . . . C5 C 0.49568(13) 0.5477(3) 1.09375(8) 0.0219(5) Uani 1 1 d . . . C2 C 0.59940(13) 0.3580(3) 1.05936(8) 0.0194(4) Uani 1 1 d . . . C9 C 0.71671(13) 0.6698(3) 1.14546(9) 0.0210(5) Uani 1 1 d . . . C13 C 0.86605(15) 0.7390(4) 1.20260(10) 0.0295(5) Uani 1 1 d . . . C1 C 0.71015(13) 0.5057(3) 1.02366(8) 0.0189(4) Uani 1 1 d . . . C11 C 0.76523(15) 0.5943(3) 1.24668(10) 0.0284(5) Uani 1 1 d . . . C12 C 0.84689(15) 0.6655(3) 1.24934(9) 0.0292(5) Uani 1 1 d . . . C8 C 0.54856(15) 0.1815(3) 1.05237(10) 0.0254(5) Uani 1 1 d . . . C6 C 0.40228(15) 0.7770(4) 1.11588(11) 0.0322(6) Uani 1 1 d . . . C7 C 0.4166(2) 0.7678(5) 1.17865(13) 0.0444(7) Uani 1 1 d . . . H4 H 0.6128(15) 0.803(3) 1.0830(9) 0.020(6) Uiso 1 1 d . . . H11 H 0.7565(15) 0.547(3) 1.2815(10) 0.023(6) Uiso 1 1 d . . . H8A H 0.5565(18) 0.128(4) 1.0903(12) 0.041(7) Uiso 1 1 d . . . H14 H 0.8140(16) 0.791(4) 1.1174(10) 0.028(6) Uiso 1 1 d . . . H1N H 0.6905(18) 0.248(4) 1.0305(11) 0.038(8) Uiso 1 1 d . . . H13 H 0.924(2) 0.795(4) 1.2047(12) 0.050(8) Uiso 1 1 d . . . H10 H 0.6427(18) 0.552(4) 1.1916(10) 0.034(7) Uiso 1 1 d . . . H7B H 0.431(2) 0.653(5) 1.1928(13) 0.055(9) Uiso 1 1 d . . . H7A H 0.467(2) 0.851(5) 1.2007(13) 0.059(9) Uiso 1 1 d . . . H2N H 0.7015(17) 0.770(4) 1.0267(10) 0.033(7) Uiso 1 1 d . . . H6A H 0.3553(18) 0.694(4) 1.0940(12) 0.042(7) Uiso 1 1 d . . . H6B H 0.394(2) 0.901(5) 1.1027(12) 0.051(9) Uiso 1 1 d . . . H8B H 0.564(2) 0.103(5) 1.0267(13) 0.056(9) Uiso 1 1 d . . . H8C H 0.486(2) 0.207(5) 1.0376(13) 0.064(10) Uiso 1 1 d . . . H7C H 0.365(2) 0.815(5) 1.1878(14) 0.072(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0205(7) 0.0187(8) 0.0305(8) 0.0002(6) 0.0147(6) -0.0004(6) F1 0.0289(7) 0.0582(11) 0.0350(8) -0.0028(7) -0.0005(6) -0.0023(7) O3 0.0195(8) 0.0263(9) 0.0417(9) -0.0013(7) 0.0166(7) 0.0036(6) O2 0.0204(8) 0.0341(10) 0.0475(10) -0.0047(8) 0.0177(7) -0.0073(7) N1 0.0198(9) 0.0157(9) 0.0305(9) -0.0002(7) 0.0130(7) -0.0010(7) N2 0.0215(9) 0.0161(9) 0.0272(9) 0.0006(7) 0.0135(7) -0.0016(7) C4 0.0187(10) 0.0174(11) 0.0258(10) -0.0003(8) 0.0109(8) -0.0002(8) C10 0.0216(11) 0.0251(12) 0.0295(11) -0.0016(9) 0.0099(9) -0.0034(9) C3 0.0166(10) 0.0196(11) 0.0217(10) 0.0004(8) 0.0064(8) -0.0010(8) C14 0.0228(11) 0.0242(12) 0.0324(12) -0.0041(9) 0.0135(9) -0.0051(9) C5 0.0174(10) 0.0247(12) 0.0238(10) -0.0008(9) 0.0063(8) 0.0004(9) C2 0.0159(9) 0.0216(11) 0.0212(9) 0.0028(8) 0.0063(8) -0.0005(8) C9 0.0203(10) 0.0163(11) 0.0289(11) -0.0046(8) 0.0113(8) 0.0000(8) C13 0.0197(11) 0.0302(13) 0.0398(13) -0.0066(10) 0.0106(10) -0.0032(9) C1 0.0165(9) 0.0177(10) 0.0229(10) 0.0003(8) 0.0065(8) 0.0011(8) C11 0.0304(13) 0.0285(13) 0.0282(11) 0.0008(9) 0.0114(9) -0.0003(10) C12 0.0261(11) 0.0287(13) 0.0293(11) -0.0061(9) 0.0024(9) 0.0024(10) C8 0.0242(11) 0.0219(12) 0.0326(12) -0.0023(10) 0.0125(9) -0.0033(9) C6 0.0191(11) 0.0351(15) 0.0458(14) -0.0041(12) 0.0149(10) 0.0074(10) C7 0.0523(18) 0.0395(17) 0.0506(17) -0.0047(14) 0.0294(14) 0.0068(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.244(2) . ? F1 C12 1.362(3) . ? O3 C5 1.351(3) . ? O3 C6 1.455(3) . ? O2 C5 1.206(3) . ? N1 C1 1.379(3) . ? N1 C2 1.390(3) . ? N1 H1N 0.85(3) . ? N2 C1 1.331(3) . ? N2 C4 1.466(3) . ? N2 H2N 0.90(3) . ? C4 C3 1.509(3) . ? C4 C9 1.535(3) . ? C4 H4 1.05(2) . ? C10 C11 1.384(3) . ? C10 C9 1.385(3) . ? C10 H10 0.96(3) . ? C3 C2 1.346(3) . ? C3 C5 1.470(3) . ? C14 C13 1.387(3) . ? C14 C9 1.389(3) . ? C14 H14 0.96(3) . ? C2 C8 1.496(3) . ? C13 C12 1.366(3) . ? C13 H13 0.98(3) . ? C11 C12 1.376(3) . ? C11 H11 0.96(2) . ? C8 H8A 0.97(3) . ? C8 H8B 0.93(3) . ? C8 H8C 0.97(3) . ? C6 C7 1.476(4) . ? C6 H6A 0.98(3) . ? C6 H6B 0.95(3) . ? C7 H7B 0.91(4) . ? C7 H7A 1.02(4) . ? C7 H7C 0.97(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O3 C6 116.66(18) . . ? C1 N1 C2 121.88(18) . . ? C1 N1 H1N 116.2(19) . . ? C2 N1 H1N 119.1(19) . . ? C1 N2 C4 120.61(18) . . ? C1 N2 H2N 118.6(17) . . ? C4 N2 H2N 119.0(17) . . ? N2 C4 C3 107.54(16) . . ? N2 C4 C9 111.09(16) . . ? C3 C4 C9 113.12(17) . . ? N2 C4 H4 105.2(12) . . ? C3 C4 H4 110.9(13) . . ? C9 C4 H4 108.7(12) . . ? C11 C10 C9 121.4(2) . . ? C11 C10 H10 119.4(15) . . ? C9 C10 H10 119.2(15) . . ? C2 C3 C5 122.27(19) . . ? C2 C3 C4 117.74(18) . . ? C5 C3 C4 119.98(18) . . ? C13 C14 C9 121.2(2) . . ? C13 C14 H14 118.1(15) . . ? C9 C14 H14 120.6(15) . . ? O2 C5 O3 123.09(19) . . ? O2 C5 C3 126.2(2) . . ? O3 C5 C3 110.70(18) . . ? C3 C2 N1 118.14(19) . . ? C3 C2 C8 127.44(18) . . ? N1 C2 C8 114.41(19) . . ? C10 C9 C14 118.4(2) . . ? C10 C9 C4 121.47(18) . . ? C14 C9 C4 120.13(19) . . ? C12 C13 C14 118.2(2) . . ? C12 C13 H13 122.9(17) . . ? C14 C13 H13 118.8(17) . . ? O1 C1 N2 124.11(19) . . ? O1 C1 N1 120.18(19) . . ? N2 C1 N1 115.69(18) . . ? C12 C11 C10 118.1(2) . . ? C12 C11 H11 117.9(14) . . ? C10 C11 H11 124.0(14) . . ? F1 C12 C13 118.7(2) . . ? F1 C12 C11 118.5(2) . . ? C13 C12 C11 122.8(2) . . ? C2 C8 H8A 108.7(17) . . ? C2 C8 H8B 111(2) . . ? H8A C8 H8B 114(3) . . ? C2 C8 H8C 109(2) . . ? H8A C8 H8C 105(2) . . ? H8B C8 H8C 108(3) . . ? O3 C6 C7 110.9(2) . . ? O3 C6 H6A 107.2(16) . . ? C7 C6 H6A 113.3(16) . . ? O3 C6 H6B 101.4(19) . . ? C7 C6 H6B 110.7(18) . . ? H6A C6 H6B 113(2) . . ? C6 C7 H7B 112(2) . . ? C6 C7 H7A 112.1(18) . . ? H7B C7 H7A 106(3) . . ? C6 C7 H7C 110(2) . . ? H7B C7 H7C 112(3) . . ? H7A C7 H7C 104(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N2 C4 C3 -45.4(2) . . . . ? C1 N2 C4 C9 78.9(2) . . . . ? N2 C4 C3 C2 37.2(2) . . . . ? C9 C4 C3 C2 -85.8(2) . . . . ? N2 C4 C3 C5 -141.89(18) . . . . ? C9 C4 C3 C5 95.1(2) . . . . ? C6 O3 C5 O2 1.2(3) . . . . ? C6 O3 C5 C3 -179.58(17) . . . . ? C2 C3 C5 O2 12.4(3) . . . . ? C4 C3 C5 O2 -168.6(2) . . . . ? C2 C3 C5 O3 -166.82(18) . . . . ? C4 C3 C5 O3 12.2(3) . . . . ? C5 C3 C2 N1 172.80(17) . . . . ? C4 C3 C2 N1 -6.3(3) . . . . ? C5 C3 C2 C8 -5.8(3) . . . . ? C4 C3 C2 C8 175.15(19) . . . . ? C1 N1 C2 C3 -24.0(3) . . . . ? C1 N1 C2 C8 154.73(19) . . . . ? C11 C10 C9 C14 -0.5(3) . . . . ? C11 C10 C9 C4 -179.3(2) . . . . ? C13 C14 C9 C10 1.0(3) . . . . ? C13 C14 C9 C4 179.8(2) . . . . ? N2 C4 C9 C10 -151.2(2) . . . . ? C3 C4 C9 C10 -30.1(3) . . . . ? N2 C4 C9 C14 30.1(3) . . . . ? C3 C4 C9 C14 151.1(2) . . . . ? C9 C14 C13 C12 -0.8(4) . . . . ? C4 N2 C1 O1 -161.78(19) . . . . ? C4 N2 C1 N1 19.9(3) . . . . ? C2 N1 C1 O1 -160.96(18) . . . . ? C2 N1 C1 N2 17.4(3) . . . . ? C9 C10 C11 C12 -0.1(3) . . . . ? C14 C13 C12 F1 179.8(2) . . . . ? C14 C13 C12 C11 0.1(4) . . . . ? C10 C11 C12 F1 -179.4(2) . . . . ? C10 C11 C12 C13 0.3(4) . . . . ? C5 O3 C6 C7 86.8(3) . . . . ? #===END # Attachment '- PYOX2b.cif' # CIF-file generated for LTO4FB in P2(1)/n #============================================================================== data_lto4fb _database_code_depnum_ccdc_archive 'CCDC 761380' #TrackingRef '- PYOX2b.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H15 F N2 O3, C13 H12 F N2 O3, C H3' _chemical_formula_sum 'C28 H30 F2 N4 O6' _chemical_formula_structural ? _chemical_formula_iupac ? _chemical_formula_weight 556.56 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z _cell_length_a 12.0087(7) _cell_length_b 7.3445(4) _cell_length_c 29.8816(15) _cell_angle_alpha 90 _cell_angle_beta 92.941(4) _cell_angle_gamma 90 _cell_volume 2632.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 540 _cell_measurement_theta_min 0.98 _cell_measurement_theta_max 27.97 _cell_special_details ; ; _exptl_crystal_description ' Rod' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.11 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.405 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.109 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.9775 _exptl_absorpt_correction_T_max 0.9881 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 120 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Goniometer Xcalibur, detector: Eos (Nova)' _diffrn_detector_area_resol_mean 16.0839 _diffrn_orient_matrix_UB_11 0.0471248803 _diffrn_orient_matrix_UB_12 0.0364363768 _diffrn_orient_matrix_UB_13 -0.0102735272 _diffrn_orient_matrix_UB_21 0.0142465702 _diffrn_orient_matrix_UB_22 0.0503096249 _diffrn_orient_matrix_UB_23 0.0197362307 _diffrn_orient_matrix_UB_31 0.0328860011 _diffrn_orient_matrix_UB_32 -0.0739510025 _diffrn_orient_matrix_UB_33 0.0083645841 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -54.00 4.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.0427 96.0000 172.0000 58 #__ type_ start__ end____ width___ exp.time_ 2 omega 13.00 51.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.0427 53.0000 -53.0000 38 #__ type_ start__ end____ width___ exp.time_ 3 omega -5.00 83.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 37.0000 120.0000 88 #__ type_ start__ end____ width___ exp.time_ 4 omega -11.00 77.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 77.0000 -30.0000 88 #__ type_ start__ end____ width___ exp.time_ 5 omega -90.00 9.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.0427 -37.0000 150.0000 99 #__ type_ start__ end____ width___ exp.time_ 6 omega -94.00 -34.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.0427 179.0000 -30.0000 60 #__ type_ start__ end____ width___ exp.time_ 7 omega -87.00 -40.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.0427 -53.0000 -17.0000 47 #__ type_ start__ end____ width___ exp.time_ 8 omega -51.00 40.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 -53.0000 -126.0000 91 ; _diffrn_measurement_method '\w scans' # number of measured reflections (redundant set) _diffrn_reflns_number 30240 _diffrn_reflns_av_R_equivalents 0.1127 _diffrn_reflns_av_sigmaI/netI 0.2378 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 29.36 _diffrn_measured_fraction_theta_max 0.891 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_reduction_process ; ; _reflns_number_total 6454 _reflns_number_gt 2388 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (2009) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0666P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6454 _refine_ls_number_parameters 374 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.1989 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1186 _refine_ls_wR_factor_gt 0.0958 _refine_ls_goodness_of_fit_ref 0.809 _refine_ls_restrained_S_all 0.809 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.273 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.061 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT 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 C6A C 0.1312(6) 0.7868(8) -0.0196(2) 0.0248(13) Uani 0.630(8) 1 d PU A 1 H6A1 H 0.0884 0.6862 -0.0343 0.030 Uiso 0.630(8) 1 calc PR A 1 H6A2 H 0.0975 0.9042 -0.0293 0.030 Uiso 0.630(8) 1 calc PR A 1 C7A C 0.2520(5) 0.7782(7) -0.03075(19) 0.0441(14) Uani 0.639(6) 1 d P A 1 H7A1 H 0.2944 0.8703 -0.0133 0.066 Uiso 0.639(6) 1 calc PR A 1 H7A2 H 0.2584 0.8016 -0.0628 0.066 Uiso 0.639(6) 1 calc PR A 1 H7A3 H 0.2818 0.6571 -0.0234 0.066 Uiso 0.639(6) 1 calc PR A 1 C7B C 0.0903(8) 0.8104(13) -0.0426(3) 0.0441(14) Uani 0.361(6) 1 d P A 2 H7B1 H 0.0534 0.6917 -0.0412 0.066 Uiso 0.361(6) 1 calc PR A 2 H7B2 H 0.1136 0.8317 -0.0731 0.066 Uiso 0.361(6) 1 calc PR A 2 H7B3 H 0.0383 0.9062 -0.0344 0.066 Uiso 0.361(6) 1 calc PR A 2 C6B C 0.1901(12) 0.8129(14) -0.0107(3) 0.0248(13) Uani 0.370(8) 1 d PU A 2 H6B1 H 0.2456 0.7193 -0.0181 0.030 Uiso 0.370(8) 1 calc PR A 2 H6B2 H 0.2261 0.9341 -0.0091 0.030 Uiso 0.370(8) 1 calc PR A 2 O1' O 1.13845(15) 1.0873(2) 0.21098(5) 0.0179(4) Uani 1 1 d . . . O1 O 0.12829(14) 0.5796(2) 0.22869(5) 0.0173(4) Uani 1 1 d . . . N2' N 1.11277(17) 0.9258(3) 0.27463(6) 0.0172(5) Uani 1 1 d . . . H2N' H 1.1429 0.8264 0.2641 0.021 Uiso 1 1 calc R . . N1' N 1.10439(17) 1.2367(3) 0.27584(6) 0.0170(5) Uani 1 1 d . . . H1N' H 1.0946 1.3403 0.2613 0.020 Uiso 1 1 calc R . . N1 N 0.11077(18) 0.4307(3) 0.16203(6) 0.0181(5) Uani 1 1 d . . . H1N H 0.0956 0.3279 0.1756 0.022 Uiso 1 1 calc R . . N2 N 0.12019(17) 0.7424(3) 0.16391(6) 0.0174(6) Uani 1 1 d . . . H2N H 0.1461 0.8416 0.1773 0.021 Uiso 1 1 calc R . . O3' O 1.07604(16) 0.8968(2) 0.40646(5) 0.0270(5) Uani 1 1 d . . . F1' F 0.59418(13) 0.7984(2) 0.28885(5) 0.0401(5) Uani 1 1 d . . . C3' C 1.0875(2) 1.0833(4) 0.34441(8) 0.0154(6) Uani 1 1 d . . . F1 F -0.38449(14) 0.8780(2) 0.10191(6) 0.0474(5) Uani 1 1 d . . . C3 C 0.1153(2) 0.5827(4) 0.09273(8) 0.0200(7) Uani 1 1 d . . . O2' O 1.10997(17) 1.1935(3) 0.42020(6) 0.0327(6) Uani 1 1 d . . . C1 C 0.1191(2) 0.5873(4) 0.18738(9) 0.0162(6) Uani 1 1 d . . . C5' C 1.0941(2) 1.0719(4) 0.39348(9) 0.0233(7) Uani 1 1 d . . . C5 C 0.1363(3) 0.5933(4) 0.04517(9) 0.0313(8) Uani 1 1 d . A . O2 O 0.1532(2) 0.4670(3) 0.02009(6) 0.0436(7) Uani 1 1 d . . . C1' C 1.1192(2) 1.0806(4) 0.25114(9) 0.0165(6) Uani 1 1 d . . . C2 C 0.1251(2) 0.4269(4) 0.11595(8) 0.0182(7) Uani 1 1 d . . . C11' C 0.7428(2) 0.9267(4) 0.33223(9) 0.0271(7) Uani 1 1 d . . . H11' H 0.6922 0.9736 0.3528 0.032 Uiso 1 1 calc R . . C14' C 0.8891(2) 0.7845(4) 0.27283(9) 0.0240(7) Uani 1 1 d . . . H14' H 0.9393 0.7340 0.2526 0.029 Uiso 1 1 calc R . . C13' C 0.7758(2) 0.7557(4) 0.26551(9) 0.0278(8) Uani 1 1 d . . . H13' H 0.7475 0.6877 0.2404 0.033 Uiso 1 1 calc R . . C2' C 1.1041(2) 1.2396(4) 0.32254(8) 0.0162(6) Uani 1 1 d . . . O3 O 0.13307(19) 0.7682(3) 0.03088(6) 0.0460(7) Uani 1 1 d . . . C14 C -0.0987(2) 0.8871(4) 0.14504(9) 0.0243(7) Uani 1 1 d . . . H14 H -0.0555 0.9356 0.1698 0.029 Uiso 1 1 calc R . . C4' C 1.0578(2) 0.9157(4) 0.31701(8) 0.0172(6) Uani 1 1 d . . . H4' H 1.0888 0.8078 0.3338 0.021 Uiso 1 1 calc R . . C12' C 0.7054(2) 0.8280(4) 0.29559(10) 0.0247(7) Uani 1 1 d . . . C11 C -0.2248(3) 0.7511(4) 0.07308(9) 0.0271(8) Uani 1 1 d . . . H11 H -0.2686 0.7049 0.0482 0.033 Uiso 1 1 calc R . . C10' C 0.8555(2) 0.9559(4) 0.33838(9) 0.0238(7) Uani 1 1 d . . . H10' H 0.8825 1.0259 0.3634 0.029 Uiso 1 1 calc R . . C8' C 1.1193(2) 1.4259(3) 0.34145(8) 0.0242(7) Uani 1 1 d . . . H8'A H 1.0474 1.4895 0.3402 0.036 Uiso 1 1 calc R . . H8'B H 1.1724 1.4935 0.3240 0.036 Uiso 1 1 calc R . . H8'C H 1.1479 1.4174 0.3727 0.036 Uiso 1 1 calc R . . C9' C 0.9312(2) 0.8864(3) 0.30928(8) 0.0165(6) Uani 1 1 d . . . C10 C -0.1107(2) 0.7194(4) 0.07668(9) 0.0247(7) Uani 1 1 d . . . H10 H -0.0762 0.6517 0.0541 0.030 Uiso 1 1 calc R . . C9 C -0.0468(2) 0.7862(3) 0.11307(9) 0.0188(7) Uani 1 1 d . . . C8 C 0.1502(3) 0.2398(3) 0.09958(8) 0.0298(8) Uani 1 1 d . . . H8A H 0.1521 0.2411 0.0668 0.045 Uiso 1 1 calc R . . H8B H 0.0921 0.1555 0.1086 0.045 Uiso 1 1 calc R . . H8C H 0.2227 0.2001 0.1126 0.045 Uiso 1 1 calc R . . C4 C 0.0800(2) 0.7537(3) 0.11688(8) 0.0191(7) Uani 1 1 d . . . H4 H 0.1171 0.8602 0.1031 0.023 Uiso 1 1 calc R . . C6' C 1.0672(3) 0.8718(4) 0.45426(8) 0.0372(9) Uani 1 1 d . . . H6'A H 1.0016 0.9385 0.4646 0.045 Uiso 1 1 calc R . . H6'B H 1.1347 0.9195 0.4707 0.045 Uiso 1 1 calc R . . C13 C -0.2125(2) 0.9188(4) 0.14175(10) 0.0286(8) Uani 1 1 d . . . H13 H -0.2478 0.9872 0.1639 0.034 Uiso 1 1 calc R . . C12 C -0.2729(2) 0.8481(4) 0.10530(10) 0.0288(8) Uani 1 1 d . . . C7' C 1.0552(3) 0.6749(4) 0.46300(10) 0.0582(12) Uani 1 1 d . . . H7'A H 0.9903 0.6278 0.4455 0.087 Uiso 1 1 calc R . . H7'B H 1.0451 0.6554 0.4950 0.087 Uiso 1 1 calc R . . H7'C H 1.1224 0.6110 0.4543 0.087 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C6A 0.025(3) 0.026(2) 0.024(2) 0.0072(18) 0.001(3) -0.002(2) C7A 0.048(4) 0.044(3) 0.041(3) 0.018(3) 0.005(3) 0.004(3) C7B 0.048(4) 0.044(3) 0.041(3) 0.018(3) 0.005(3) 0.004(3) C6B 0.025(3) 0.026(2) 0.024(2) 0.0072(18) 0.001(3) -0.002(2) O1' 0.0258(11) 0.0144(10) 0.0136(10) -0.0012(9) 0.0040(9) 0.0010(9) O1 0.0227(11) 0.0154(10) 0.0136(10) -0.0014(9) -0.0012(9) 0.0007(9) N2' 0.0188(13) 0.0142(12) 0.0192(13) -0.0012(11) 0.0053(11) 0.0019(11) N1' 0.0261(14) 0.0112(12) 0.0136(12) 0.0031(11) 0.0011(11) 0.0045(11) N1 0.0307(15) 0.0080(12) 0.0157(12) 0.0024(11) 0.0038(11) -0.0042(11) N2 0.0243(14) 0.0101(12) 0.0174(12) -0.0008(11) -0.0039(11) -0.0044(11) O3' 0.0433(13) 0.0257(12) 0.0121(10) 0.0018(9) 0.0024(10) -0.0099(11) F1' 0.0204(10) 0.0528(12) 0.0469(11) -0.0116(10) 0.0005(9) -0.0061(9) C3' 0.0173(16) 0.0157(15) 0.0131(14) -0.0023(13) 0.0006(12) -0.0022(13) F1 0.0233(11) 0.0555(12) 0.0627(13) 0.0144(10) -0.0051(10) 0.0051(10) C3 0.0310(18) 0.0151(15) 0.0140(15) 0.0003(14) 0.0029(14) 0.0045(15) O2' 0.0513(15) 0.0269(12) 0.0197(11) -0.0063(10) -0.0004(11) -0.0042(11) C1 0.0130(16) 0.0146(15) 0.0210(17) -0.0002(15) 0.0010(13) -0.0013(13) C5' 0.0254(18) 0.0211(17) 0.0237(17) 0.0014(15) 0.0024(15) 0.0012(15) C5 0.050(2) 0.0225(18) 0.0218(17) 0.0071(16) 0.0061(17) 0.0111(17) O2 0.0847(19) 0.0276(12) 0.0196(12) -0.0026(10) 0.0116(12) 0.0164(13) C1' 0.0138(15) 0.0163(16) 0.0193(16) 0.0018(14) 0.0006(13) 0.0016(13) C2 0.0224(17) 0.0187(16) 0.0139(15) -0.0016(14) 0.0056(13) 0.0003(14) C11' 0.0248(18) 0.0281(17) 0.0290(18) -0.0091(16) 0.0089(15) 0.0002(16) C14' 0.0272(19) 0.0243(17) 0.0212(17) -0.0049(14) 0.0067(15) -0.0030(15) C13' 0.0256(19) 0.0301(18) 0.0275(18) -0.0113(15) -0.0017(15) -0.0069(16) C2' 0.0145(16) 0.0196(16) 0.0148(15) -0.0036(13) 0.0035(12) -0.0003(13) O3 0.091(2) 0.0269(12) 0.0229(12) 0.0130(10) 0.0278(13) 0.0139(13) C14 0.031(2) 0.0218(17) 0.0197(16) -0.0016(14) -0.0010(15) -0.0015(15) C4' 0.0214(17) 0.0176(15) 0.0131(15) 0.0013(13) 0.0052(13) 0.0011(14) C12' 0.0156(18) 0.0248(17) 0.0337(19) 0.0008(15) 0.0006(16) -0.0050(14) C11 0.030(2) 0.0249(17) 0.0255(17) 0.0044(15) -0.0103(15) -0.0017(16) C10' 0.0276(19) 0.0227(17) 0.0211(17) -0.0078(14) 0.0010(15) -0.0012(14) C8' 0.0282(18) 0.0202(16) 0.0241(16) -0.0039(14) 0.0026(14) -0.0016(15) C9' 0.0208(16) 0.0127(15) 0.0160(15) 0.0022(13) 0.0003(13) -0.0027(13) C10 0.037(2) 0.0199(16) 0.0165(16) -0.0004(14) -0.0023(15) 0.0014(15) C9 0.0247(18) 0.0129(15) 0.0186(16) 0.0014(13) -0.0017(14) 0.0016(13) C8 0.052(2) 0.0181(16) 0.0192(16) -0.0018(14) 0.0018(16) 0.0089(16) C4 0.0269(18) 0.0180(15) 0.0126(15) -0.0006(13) 0.0038(13) 0.0000(14) C6' 0.056(2) 0.041(2) 0.0148(17) 0.0036(15) -0.0005(17) -0.0139(18) C13 0.030(2) 0.0249(17) 0.0318(18) -0.0017(16) 0.0039(16) 0.0071(16) C12 0.0175(19) 0.0276(18) 0.041(2) 0.0138(16) -0.0009(17) 0.0034(15) C7' 0.102(3) 0.047(2) 0.0250(19) 0.0142(18) 0.003(2) -0.029(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C6A C7A 1.506(8) . ? C6A O3 1.514(6) . ? C6A H6A1 0.9900 . ? C6A H6A2 0.9900 . ? C7A H7A1 0.9800 . ? C7A H7A2 0.9800 . ? C7A H7A3 0.9800 . ? C7B C6B 1.493(15) . ? C7B H7B1 0.9800 . ? C7B H7B2 0.9800 . ? C7B H7B3 0.9800 . ? C6B O3 1.486(11) . ? C6B H6B1 0.9900 . ? C6B H6B2 0.9900 . ? O1' C1' 1.235(3) . ? O1 C1 1.235(3) . ? N2' C1' 1.341(3) . ? N2' C4' 1.459(3) . ? N2' H2N' 0.8800 . ? N1' C1' 1.380(3) . ? N1' C2' 1.396(3) . ? N1' H1N' 0.8800 . ? N1 C1 1.378(3) . ? N1 C2 1.396(3) . ? N1 H1N 0.8800 . ? N2 C1 1.338(3) . ? N2 C4 1.465(3) . ? N2 H2N 0.8800 . ? O3' C5' 1.364(3) . ? O3' C6' 1.450(3) . ? F1' C12' 1.358(3) . ? C3' C2' 1.341(3) . ? C3' C5' 1.467(3) . ? C3' C4' 1.511(3) . ? F1 C12 1.356(3) . ? C3 C2 1.341(3) . ? C3 C5 1.458(3) . ? C3 C4 1.520(3) . ? O2' C5' 1.206(3) . ? C5 O2 1.216(3) . ? C5 O3 1.354(3) . ? C2 C8 1.494(3) . ? C11' C12' 1.369(3) . ? C11' C10' 1.374(4) . ? C11' H11' 0.9500 . ? C14' C13' 1.384(4) . ? C14' C9' 1.395(3) . ? C14' H14' 0.9500 . ? C13' C12' 1.372(4) . ? C13' H13' 0.9500 . ? C2' C8' 1.488(3) . ? C14 C9 1.383(3) . ? C14 C13 1.384(4) . ? C14 H14 0.9500 . ? C4' C9' 1.542(4) . ? C4' H4' 1.0000 . ? C11 C12 1.351(4) . ? C11 C10 1.389(4) . ? C11 H11 0.9500 . ? C10' C9' 1.387(3) . ? C10' H10' 0.9500 . ? C8' H8'A 0.9800 . ? C8' H8'B 0.9800 . ? C8' H8'C 0.9800 . ? C10 C9 1.388(3) . ? C10 H10 0.9500 . ? C9 C4 1.539(4) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C4 H4 1.0000 . ? C6' C7' 1.477(4) . ? C6' H6'A 0.9900 . ? C6' H6'B 0.9900 . ? C13 C12 1.379(4) . ? C13 H13 0.9500 . ? C7' H7'A 0.9800 . ? C7' H7'B 0.9800 . ? C7' H7'C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7A C6A O3 104.6(6) . . ? C7A C6A H6A1 110.8 . . ? O3 C6A H6A1 110.8 . . ? C7A C6A H6A2 110.8 . . ? O3 C6A H6A2 110.8 . . ? H6A1 C6A H6A2 108.9 . . ? C6B C7B H7B1 109.5 . . ? C6B C7B H7B2 109.5 . . ? H7B1 C7B H7B2 109.5 . . ? C6B C7B H7B3 109.5 . . ? H7B1 C7B H7B3 109.5 . . ? H7B2 C7B H7B3 109.5 . . ? O3 C6B C7B 98.2(10) . . ? O3 C6B H6B1 112.1 . . ? C7B C6B H6B1 112.1 . . ? O3 C6B H6B2 112.1 . . ? C7B C6B H6B2 112.1 . . ? H6B1 C6B H6B2 109.8 . . ? C1' N2' C4' 122.5(2) . . ? C1' N2' H2N' 118.7 . . ? C4' N2' H2N' 118.7 . . ? C1' N1' C2' 123.6(2) . . ? C1' N1' H1N' 118.2 . . ? C2' N1' H1N' 118.2 . . ? C1 N1 C2 123.3(2) . . ? C1 N1 H1N 118.3 . . ? C2 N1 H1N 118.3 . . ? C1 N2 C4 122.7(2) . . ? C1 N2 H2N 118.7 . . ? C4 N2 H2N 118.7 . . ? C5' O3' C6' 114.9(2) . . ? C2' C3' C5' 122.3(2) . . ? C2' C3' C4' 118.0(2) . . ? C5' C3' C4' 119.6(2) . . ? C2 C3 C5 122.3(2) . . ? C2 C3 C4 118.6(2) . . ? C5 C3 C4 119.0(2) . . ? O1 C1 N2 124.1(2) . . ? O1 C1 N1 120.8(2) . . ? N2 C1 N1 115.1(2) . . ? O2' C5' O3' 122.1(2) . . ? O2' C5' C3' 128.2(3) . . ? O3' C5' C3' 109.7(2) . . ? O2 C5 O3 122.1(3) . . ? O2 C5 C3 127.1(3) . . ? O3 C5 C3 110.7(2) . . ? O1' C1' N2' 124.2(3) . . ? O1' C1' N1' 121.5(2) . . ? N2' C1' N1' 114.3(2) . . ? C3 C2 N1 118.7(2) . . ? C3 C2 C8 129.0(2) . . ? N1 C2 C8 112.2(2) . . ? C12' C11' C10' 118.0(3) . . ? C12' C11' H11' 121.0 . . ? C10' C11' H11' 121.0 . . ? C13' C14' C9' 121.3(3) . . ? C13' C14' H14' 119.4 . . ? C9' C14' H14' 119.4 . . ? C12' C13' C14' 118.1(3) . . ? C12' C13' H13' 121.0 . . ? C14' C13' H13' 121.0 . . ? C3' C2' N1' 118.8(2) . . ? C3' C2' C8' 128.3(2) . . ? N1' C2' C8' 112.8(2) . . ? C5 O3 C6B 117.8(5) . . ? C5 O3 C6A 113.5(3) . . ? C9 C14 C13 121.3(3) . . ? C9 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? N2' C4' C3' 108.9(2) . . ? N2' C4' C9' 111.3(2) . . ? C3' C4' C9' 113.5(2) . . ? N2' C4' H4' 107.6 . . ? C3' C4' H4' 107.6 . . ? C9' C4' H4' 107.6 . . ? F1' C12' C11' 118.9(3) . . ? F1' C12' C13' 118.4(3) . . ? C11' C12' C13' 122.8(3) . . ? C12 C11 C10 119.3(3) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? C11' C10' C9' 122.1(3) . . ? C11' C10' H10' 118.9 . . ? C9' C10' H10' 118.9 . . ? C2' C8' H8'A 109.5 . . ? C2' C8' H8'B 109.5 . . ? H8'A C8' H8'B 109.5 . . ? C2' C8' H8'C 109.5 . . ? H8'A C8' H8'C 109.5 . . ? H8'B C8' H8'C 109.5 . . ? C10' C9' C14' 117.7(3) . . ? C10' C9' C4' 121.8(2) . . ? C14' C9' C4' 120.5(2) . . ? C9 C10 C11 120.4(3) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C14 C9 C10 118.6(3) . . ? C14 C9 C4 120.8(2) . . ? C10 C9 C4 120.6(3) . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C4 C3 108.8(2) . . ? N2 C4 C9 110.9(2) . . ? C3 C4 C9 113.1(2) . . ? N2 C4 H4 108.0 . . ? C3 C4 H4 108.0 . . ? C9 C4 H4 108.0 . . ? O3' C6' C7' 108.1(2) . . ? O3' C6' H6'A 110.1 . . ? C7' C6' H6'A 110.1 . . ? O3' C6' H6'B 110.1 . . ? C7' C6' H6'B 110.1 . . ? H6'A C6' H6'B 108.4 . . ? C12 C13 C14 118.1(3) . . ? C12 C13 H13 121.0 . . ? C14 C13 H13 121.0 . . ? C11 C12 F1 119.3(3) . . ? C11 C12 C13 122.3(3) . . ? F1 C12 C13 118.4(3) . . ? C6' C7' H7'A 109.5 . . ? C6' C7' H7'B 109.5 . . ? H7'A C7' H7'B 109.5 . . ? C6' C7' H7'C 109.5 . . ? H7'A C7' H7'C 109.5 . . ? H7'B C7' H7'C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N2 C1 O1 -163.1(2) . . . . ? C4 N2 C1 N1 19.0(4) . . . . ? C2 N1 C1 O1 -165.3(2) . . . . ? C2 N1 C1 N2 12.7(4) . . . . ? C6' O3' C5' O2' 5.5(4) . . . . ? C6' O3' C5' C3' -172.9(2) . . . . ? C2' C3' C5' O2' 3.1(5) . . . . ? C4' C3' C5' O2' -175.2(3) . . . . ? C2' C3' C5' O3' -178.7(3) . . . . ? C4' C3' C5' O3' 3.0(3) . . . . ? C2 C3 C5 O2 7.9(5) . . . . ? C4 C3 C5 O2 -171.5(3) . . . . ? C2 C3 C5 O3 -173.1(3) . . . . ? C4 C3 C5 O3 7.5(4) . . . . ? C4' N2' C1' O1' -160.8(2) . . . . ? C4' N2' C1' N1' 20.4(3) . . . . ? C2' N1' C1' O1' -167.0(2) . . . . ? C2' N1' C1' N2' 11.8(4) . . . . ? C5 C3 C2 N1 175.8(3) . . . . ? C4 C3 C2 N1 -4.8(4) . . . . ? C5 C3 C2 C8 -4.3(5) . . . . ? C4 C3 C2 C8 175.1(3) . . . . ? C1 N1 C2 C3 -19.5(4) . . . . ? C1 N1 C2 C8 160.6(2) . . . . ? C9' C14' C13' C12' -1.0(4) . . . . ? C5' C3' C2' N1' 175.4(2) . . . . ? C4' C3' C2' N1' -6.3(4) . . . . ? C5' C3' C2' C8' -7.1(5) . . . . ? C4' C3' C2' C8' 171.3(3) . . . . ? C1' N1' C2' C3' -18.5(4) . . . . ? C1' N1' C2' C8' 163.6(2) . . . . ? O2 C5 O3 C6B -22.0(7) . . . . ? C3 C5 O3 C6B 158.9(6) . . . . ? O2 C5 O3 C6A 10.6(5) . . . . ? C3 C5 O3 C6A -168.5(4) . . . . ? C7B C6B O3 C5 98.7(7) . . . . ? C7B C6B O3 C6A 9.6(7) . . . . ? C7A C6A O3 C5 -84.7(5) . . . . ? C7A C6A O3 C6B 20.7(9) . . . . ? C1' N2' C4' C3' -41.2(3) . . . . ? C1' N2' C4' C9' 84.7(3) . . . . ? C2' C3' C4' N2' 32.5(3) . . . . ? C5' C3' C4' N2' -149.2(2) . . . . ? C2' C3' C4' C9' -92.1(3) . . . . ? C5' C3' C4' C9' 86.2(3) . . . . ? C10' C11' C12' F1' -179.7(2) . . . . ? C10' C11' C12' C13' 1.0(4) . . . . ? C14' C13' C12' F1' -179.3(2) . . . . ? C14' C13' C12' C11' 0.0(4) . . . . ? C12' C11' C10' C9' -1.1(4) . . . . ? C11' C10' C9' C14' 0.2(4) . . . . ? C11' C10' C9' C4' -178.5(2) . . . . ? C13' C14' C9' C10' 0.9(4) . . . . ? C13' C14' C9' C4' 179.6(2) . . . . ? N2' C4' C9' C10' -148.3(2) . . . . ? C3' C4' C9' C10' -25.0(3) . . . . ? N2' C4' C9' C14' 33.0(3) . . . . ? C3' C4' C9' C14' 156.4(2) . . . . ? C12 C11 C10 C9 0.2(4) . . . . ? C13 C14 C9 C10 1.3(4) . . . . ? C13 C14 C9 C4 179.3(3) . . . . ? C11 C10 C9 C14 -1.1(4) . . . . ? C11 C10 C9 C4 -179.2(2) . . . . ? C1 N2 C4 C3 -39.1(3) . . . . ? C1 N2 C4 C9 85.8(3) . . . . ? C2 C3 C4 N2 30.6(3) . . . . ? C5 C3 C4 N2 -150.0(2) . . . . ? C2 C3 C4 C9 -93.1(3) . . . . ? C5 C3 C4 C9 86.4(3) . . . . ? C14 C9 C4 N2 32.6(3) . . . . ? C10 C9 C4 N2 -149.4(2) . . . . ? C14 C9 C4 C3 155.1(2) . . . . ? C10 C9 C4 C3 -26.9(3) . . . . ? C5' O3' C6' C7' -176.3(3) . . . . ? C9 C14 C13 C12 -0.6(4) . . . . ? C10 C11 C12 F1 -179.6(2) . . . . ? C10 C11 C12 C13 0.5(4) . . . . ? C14 C13 C12 C11 -0.4(4) . . . . ? C14 C13 C12 F1 179.8(2) . . . . ? #===END # Attachment '- PYOX3.cif' # CIF-file generated for O4CLP2 in P2(1)/n #============================================================================== data_o4clp2 _database_code_depnum_ccdc_archive 'CCDC 761381' #TrackingRef '- PYOX3.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H15 Cl N2 O3' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C14 H15 Cl N2 O3' _chemical_formula_iupac ? _chemical_formula_weight 294.73 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z _cell_length_a 12.7632(3) _cell_length_b 7.3290(2) _cell_length_c 29.7055(10) _cell_angle_alpha 90 _cell_angle_beta 93.705(2) _cell_angle_gamma 90 _cell_volume 2772.88(14) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 450 _cell_measurement_theta_min 0.97 _cell_measurement_theta_max 27.98 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.16 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.412 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 0.284 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.9272 _exptl_absorpt_correction_T_max 0.9559 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Goniometer Xcalibur, detector: Eos (Nova)' _diffrn_detector_area_resol_mean 16.0839 _diffrn_orient_matrix_UB_11 -0.0189938665 _diffrn_orient_matrix_UB_12 -0.0070229571 _diffrn_orient_matrix_UB_13 -0.0229127167 _diffrn_orient_matrix_UB_21 0.0499480083 _diffrn_orient_matrix_UB_22 0.0260770422 _diffrn_orient_matrix_UB_23 -0.0069692337 _diffrn_orient_matrix_UB_31 0.0154004354 _diffrn_orient_matrix_UB_32 -0.0929195453 _diffrn_orient_matrix_UB_33 -0.0002258112 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -81.00 -34.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.1989 179.0000 -60.0000 47 #__ type_ start__ end____ width___ exp.time_ 2 omega -11.00 89.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 77.0000 0.0000 100 #__ type_ start__ end____ width___ exp.time_ 3 omega -32.00 40.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 -37.0000 -120.0000 72 #__ type_ start__ end____ width___ exp.time_ 4 omega -38.00 3.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 -77.0000 150.0000 41 #__ type_ start__ end____ width___ exp.time_ 5 omega -94.00 -34.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.1989 179.0000 90.0000 60 #__ type_ start__ end____ width___ exp.time_ 6 omega -90.00 9.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.1989 -37.0000 60.0000 99 #__ type_ start__ end____ width___ exp.time_ 7 omega 5.00 57.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 -129.0000 127.0000 52 #__ type_ start__ end____ width___ exp.time_ 8 omega -11.00 89.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 77.0000 -150.0000 100 ; _diffrn_measurement_method '\w scans' # number of measured reflections (redundant set) _diffrn_reflns_number 25976 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 25.00 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 4884 # number of observed reflections (> n sig(I)) _reflns_number_gt 4131 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (2009) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0473P)^2^+2.4281P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4884 _refine_ls_number_parameters 365 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0489 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1032 _refine_ls_wR_factor_gt 0.1002 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.377 _refine_diff_density_min -0.393 _refine_diff_density_rms 0.052 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT 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 N2 N 0.88033(12) 0.2347(2) 0.33590(5) 0.0123(3) Uani 1 1 d . . . H2N H 0.8555 0.3343 0.3226 0.015 Uiso 1 1 calc R . . Cl1 Cl 1.39054(4) 0.40021(8) 0.39346(2) 0.02968(16) Uani 1 1 d . . . Cl1' Cl 0.10890(4) 0.80780(8) 0.28128(2) 0.03213(17) Uani 1 1 d . . . O1' O 0.64392(10) 1.07740(18) 0.21205(4) 0.0136(3) Uani 1 1 d . . . O3' O 0.59727(11) 0.90252(19) 0.41077(5) 0.0193(3) Uani 1 1 d . . . N2' N 0.62837(12) 0.9186(2) 0.27721(5) 0.0129(4) Uani 1 1 d . . . H2N' H 0.6590 0.8202 0.2673 0.015 Uiso 1 1 calc R . . O2 O 0.86733(12) -0.0387(2) 0.48197(5) 0.0224(3) Uani 1 1 d . . . O1 O 0.86415(10) 0.07094(18) 0.27083(4) 0.0129(3) Uani 1 1 d . . . O2' O 0.63521(12) 1.1987(2) 0.42233(5) 0.0240(4) Uani 1 1 d . . . N1' N 0.61591(12) 1.2308(2) 0.27665(5) 0.0122(3) Uani 1 1 d . . . H1N' H 0.6050 1.3328 0.2614 0.015 Uiso 1 1 calc R . . O3 O 0.88753(11) 0.26244(19) 0.47107(5) 0.0214(3) Uani 1 1 d . . . N1 N 0.88601(12) -0.0786(2) 0.33784(5) 0.0134(3) Uani 1 1 d . . . H1N H 0.8961 -0.1825 0.3239 0.016 Uiso 1 1 calc R . . C4' C 0.57695(14) 0.9112(3) 0.32005(6) 0.0120(4) Uani 1 1 d . . . H4' H 0.6060 0.8041 0.3376 0.014 Uiso 1 1 calc R . . C3 C 0.89284(14) 0.0757(3) 0.40778(6) 0.0132(4) Uani 1 1 d . . . C1' C 0.62949(13) 1.0724(3) 0.25303(6) 0.0110(4) Uani 1 1 d . . . C2 C 0.87971(14) -0.0811(3) 0.38456(6) 0.0124(4) Uani 1 1 d . . . C9' C 0.45785(14) 0.8829(3) 0.31150(6) 0.0128(4) Uani 1 1 d . . . C3' C 0.60540(14) 1.0826(3) 0.34677(7) 0.0133(4) Uani 1 1 d . . . C2' C 0.61850(14) 1.2379(3) 0.32350(6) 0.0120(4) Uani 1 1 d . . . C1 C 0.87727(13) 0.0778(3) 0.31263(6) 0.0112(4) Uani 1 1 d . . . C10 C 1.10762(16) 0.2148(3) 0.42069(7) 0.0185(4) Uani 1 1 d . . . H10 H 1.0785 0.1442 0.4436 0.022 Uiso 1 1 calc R . . C6' C 0.60038(18) 0.8786(3) 0.45949(7) 0.0250(5) Uani 1 1 d . . . H6'A H 0.5569 0.9729 0.4732 0.030 Uiso 1 1 calc R . . H6'B H 0.6734 0.8904 0.4726 0.030 Uiso 1 1 calc R . . C5 C 0.88063(15) 0.0877(3) 0.45646(7) 0.0165(4) Uani 1 1 d . . . C11 C 1.21409(16) 0.2507(3) 0.42337(7) 0.0219(5) Uani 1 1 d . . . H11 H 1.2577 0.2056 0.4480 0.026 Uiso 1 1 calc R . . C9 C 1.04228(15) 0.2804(3) 0.38487(6) 0.0145(4) Uani 1 1 d . . . C8' C 0.63401(16) 1.4274(3) 0.34167(7) 0.0173(4) Uani 1 1 d . . . H8'A H 0.5681 1.4956 0.3374 0.026 Uiso 1 1 calc R . . H8'B H 0.6886 1.4891 0.3256 0.026 Uiso 1 1 calc R . . H8'C H 0.6555 1.4216 0.3739 0.026 Uiso 1 1 calc R . . C8 C 0.85781(17) -0.2680(3) 0.40234(7) 0.0188(4) Uani 1 1 d . . . H8A H 0.8517 -0.2617 0.4350 0.028 Uiso 1 1 calc R . . H8B H 0.9154 -0.3504 0.3958 0.028 Uiso 1 1 calc R . . H8C H 0.7920 -0.3142 0.3878 0.028 Uiso 1 1 calc R . . C13 C 1.19415(17) 0.4190(3) 0.35404(8) 0.0254(5) Uani 1 1 d . . . H13 H 1.2240 0.4885 0.3311 0.030 Uiso 1 1 calc R . . C5' C 0.61513(14) 1.0746(3) 0.39641(7) 0.0151(4) Uani 1 1 d . . . C14 C 1.08737(17) 0.3830(3) 0.35183(7) 0.0229(5) Uani 1 1 d . . . H14 H 1.0441 0.4295 0.3272 0.027 Uiso 1 1 calc R . . C6 C 0.87805(18) 0.2904(3) 0.51920(7) 0.0264(5) Uani 1 1 d . . . H6A H 0.9083 0.4104 0.5281 0.032 Uiso 1 1 calc R . . H6B H 0.9184 0.1950 0.5364 0.032 Uiso 1 1 calc R . . C14' C 0.41880(16) 0.7844(3) 0.27402(7) 0.0226(5) Uani 1 1 d . . . H14' H 0.4665 0.7326 0.2543 0.027 Uiso 1 1 calc R . . C12' C 0.24341(15) 0.8336(3) 0.29374(8) 0.0204(5) Uani 1 1 d . . . C12 C 1.25662(15) 0.3524(3) 0.39000(7) 0.0198(5) Uani 1 1 d . . . C10' C 0.38641(16) 0.9522(3) 0.34032(7) 0.0208(5) Uani 1 1 d . . . H10' H 0.4113 1.0178 0.3664 0.025 Uiso 1 1 calc R . . C13' C 0.31210(16) 0.7603(3) 0.26483(8) 0.0243(5) Uani 1 1 d . . . H13' H 0.2866 0.6941 0.2389 0.029 Uiso 1 1 calc R . . C4 C 0.92342(15) 0.2460(3) 0.38267(6) 0.0133(4) Uani 1 1 d . . . H4 H 0.8898 0.3527 0.3970 0.016 Uiso 1 1 calc R . . C11' C 0.27926(17) 0.9275(3) 0.33171(8) 0.0256(5) Uani 1 1 d . . . H11' H 0.2312 0.9750 0.3518 0.031 Uiso 1 1 calc R . . C7 C 0.7654(2) 0.2835(4) 0.53074(9) 0.0373(6) Uani 1 1 d . . . H7A H 0.7250 0.3756 0.5131 0.056 Uiso 1 1 calc R . . H7B H 0.7610 0.3083 0.5630 0.056 Uiso 1 1 calc R . . H7C H 0.7366 0.1621 0.5237 0.056 Uiso 1 1 calc R . . C7' C 0.5590(2) 0.6940(4) 0.46876(8) 0.0415(7) Uani 1 1 d . . . H7'A H 0.4878 0.6820 0.4546 0.062 Uiso 1 1 calc R . . H7'B H 0.5573 0.6766 0.5014 0.062 Uiso 1 1 calc R . . H7'C H 0.6045 0.6015 0.4564 0.062 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N2 0.0165(8) 0.0089(8) 0.0113(8) 0.0015(7) -0.0015(6) 0.0012(6) Cl1 0.0169(3) 0.0360(3) 0.0363(3) -0.0091(3) 0.0025(2) -0.0060(2) Cl1' 0.0136(3) 0.0310(3) 0.0510(4) -0.0004(3) -0.0036(2) -0.0033(2) O1' 0.0161(7) 0.0132(7) 0.0116(7) -0.0004(5) 0.0014(5) 0.0003(5) O3' 0.0272(8) 0.0194(8) 0.0112(7) 0.0020(6) 0.0009(6) -0.0053(6) N2' 0.0135(8) 0.0110(9) 0.0146(9) -0.0006(7) 0.0037(6) 0.0014(6) O2 0.0360(8) 0.0186(8) 0.0130(8) 0.0016(6) 0.0038(6) -0.0023(7) O1 0.0155(7) 0.0125(7) 0.0105(7) 0.0004(5) -0.0002(5) -0.0013(5) O2' 0.0386(9) 0.0195(8) 0.0137(8) -0.0037(6) 0.0000(6) -0.0039(7) N1' 0.0158(8) 0.0082(8) 0.0127(9) 0.0015(6) 0.0008(6) 0.0015(6) O3 0.0337(8) 0.0169(8) 0.0140(8) -0.0050(6) 0.0045(6) -0.0023(6) N1 0.0191(8) 0.0088(8) 0.0123(9) -0.0017(6) 0.0019(6) 0.0026(7) C4' 0.0145(9) 0.0107(10) 0.0110(10) 0.0008(7) 0.0015(7) -0.0006(7) C3 0.0145(9) 0.0136(10) 0.0112(10) 0.0012(8) 0.0000(7) -0.0006(8) C1' 0.0067(8) 0.0133(10) 0.0130(10) -0.0007(8) -0.0003(7) 0.0001(7) C2 0.0118(9) 0.0132(10) 0.0123(10) 0.0019(8) 0.0007(7) 0.0007(8) C9' 0.0154(9) 0.0100(10) 0.0131(10) 0.0018(8) 0.0017(8) -0.0007(8) C3' 0.0117(9) 0.0150(10) 0.0132(10) -0.0020(8) 0.0008(7) 0.0000(8) C2' 0.0094(9) 0.0145(10) 0.0123(10) -0.0020(8) 0.0019(7) 0.0006(7) C1 0.0083(8) 0.0125(10) 0.0128(10) 0.0000(8) 0.0016(7) -0.0018(7) C10 0.0241(11) 0.0188(11) 0.0124(10) 0.0017(8) 0.0002(8) -0.0030(9) C6' 0.0336(12) 0.0316(13) 0.0098(11) 0.0041(9) 0.0019(9) -0.0061(10) C5 0.0177(10) 0.0155(11) 0.0162(11) -0.0021(9) 0.0015(8) 0.0000(8) C11 0.0224(11) 0.0238(12) 0.0184(11) -0.0007(9) -0.0065(8) 0.0003(9) C9 0.0205(10) 0.0107(10) 0.0123(10) -0.0024(8) 0.0002(8) -0.0018(8) C8' 0.0214(10) 0.0141(10) 0.0170(11) -0.0031(8) 0.0051(8) -0.0030(8) C8 0.0298(11) 0.0123(10) 0.0141(10) 0.0002(8) 0.0011(8) -0.0027(9) C13 0.0251(11) 0.0284(13) 0.0229(12) 0.0057(10) 0.0032(9) -0.0081(10) C5' 0.0127(9) 0.0168(11) 0.0158(11) 0.0006(9) 0.0014(8) -0.0010(8) C14 0.0249(11) 0.0245(12) 0.0186(11) 0.0080(9) -0.0042(9) -0.0041(9) C6 0.0387(13) 0.0238(12) 0.0170(12) -0.0059(9) 0.0044(10) -0.0022(10) C14' 0.0195(10) 0.0277(12) 0.0210(12) -0.0085(9) 0.0046(8) -0.0032(9) C12' 0.0135(10) 0.0176(11) 0.0299(12) 0.0034(9) -0.0005(9) -0.0023(8) C12 0.0168(10) 0.0211(11) 0.0217(12) -0.0081(9) 0.0028(8) -0.0043(8) C10' 0.0192(10) 0.0237(12) 0.0197(11) -0.0074(9) 0.0032(8) -0.0029(9) C13' 0.0210(11) 0.0285(13) 0.0229(12) -0.0074(10) -0.0018(9) -0.0068(9) C4 0.0183(10) 0.0105(10) 0.0111(10) 0.0002(8) 0.0009(7) 0.0008(8) C11' 0.0196(10) 0.0260(12) 0.0322(13) -0.0085(10) 0.0081(9) -0.0007(9) C7 0.0446(15) 0.0388(15) 0.0295(14) -0.0132(12) 0.0104(11) 0.0003(12) C7' 0.0650(18) 0.0405(16) 0.0179(13) 0.0087(11) -0.0049(12) -0.0244(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N2 C1 1.340(2) . ? N2 C4 1.463(2) . ? N2 H2N 0.8800 . ? Cl1 C12 1.741(2) . ? Cl1' C12' 1.743(2) . ? O1' C1' 1.243(2) . ? O3' C5' 1.355(2) . ? O3' C6' 1.456(2) . ? N2' C1' 1.337(2) . ? N2' C4' 1.470(2) . ? N2' H2N' 0.8800 . ? O2 C5 1.216(2) . ? O1 C1 1.243(2) . ? O2' C5' 1.208(2) . ? N1' C1' 1.373(2) . ? N1' C2' 1.391(2) . ? N1' H1N' 0.8800 . ? O3 C5 1.353(2) . ? O3 C6 1.457(2) . ? N1 C1 1.370(2) . ? N1 C2 1.396(2) . ? N1 H1N 0.8800 . ? C4' C3' 1.518(3) . ? C4' C9' 1.539(2) . ? C4' H4' 1.0000 . ? C3 C2 1.345(3) . ? C3 C5 1.467(3) . ? C3 C4 1.518(3) . ? C2 C8 1.501(3) . ? C9' C10' 1.387(3) . ? C9' C14' 1.392(3) . ? C3' C2' 1.348(3) . ? C3' C5' 1.473(3) . ? C2' C8' 1.498(3) . ? C10 C11 1.381(3) . ? C10 C9 1.394(3) . ? C10 H10 0.9500 . ? C6' C7' 1.485(3) . ? C6' H6'A 0.9900 . ? C6' H6'B 0.9900 . ? C11 C12 1.380(3) . ? C11 H11 0.9500 . ? C9 C14 1.390(3) . ? C9 C4 1.535(3) . ? C8' H8'A 0.9800 . ? C8' H8'B 0.9800 . ? C8' H8'C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C13 C12 1.380(3) . ? C13 C14 1.385(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C6 C7 1.501(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C14' C13' 1.383(3) . ? C14' H14' 0.9500 . ? C12' C11' 1.374(3) . ? C12' C13' 1.375(3) . ? C10' C11' 1.387(3) . ? C10' H10' 0.9500 . ? C13' H13' 0.9500 . ? C4 H4 1.0000 . ? C11' H11' 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C7' H7'A 0.9800 . ? C7' H7'B 0.9800 . ? C7' H7'C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N2 C4 122.35(16) . . ? C1 N2 H2N 118.8 . . ? C4 N2 H2N 118.8 . . ? C5' O3' C6' 115.51(16) . . ? C1' N2' C4' 121.15(16) . . ? C1' N2' H2N' 119.4 . . ? C4' N2' H2N' 119.4 . . ? C1' N1' C2' 123.19(16) . . ? C1' N1' H1N' 118.4 . . ? C2' N1' H1N' 118.4 . . ? C5 O3 C6 116.11(16) . . ? C1 N1 C2 123.12(16) . . ? C1 N1 H1N 118.4 . . ? C2 N1 H1N 118.4 . . ? N2' C4' C3' 108.47(15) . . ? N2' C4' C9' 110.71(15) . . ? C3' C4' C9' 113.48(15) . . ? N2' C4' H4' 108.0 . . ? C3' C4' H4' 108.0 . . ? C9' C4' H4' 108.0 . . ? C2 C3 C5 122.61(18) . . ? C2 C3 C4 118.54(17) . . ? C5 C3 C4 118.84(17) . . ? O1' C1' N2' 123.92(17) . . ? O1' C1' N1' 120.47(17) . . ? N2' C1' N1' 115.59(16) . . ? C3 C2 N1 119.06(17) . . ? C3 C2 C8 128.25(18) . . ? N1 C2 C8 112.68(16) . . ? C10' C9' C14' 117.91(18) . . ? C10' C9' C4' 122.05(17) . . ? C14' C9' C4' 120.05(17) . . ? C2' C3' C5' 122.81(18) . . ? C2' C3' C4' 117.68(17) . . ? C5' C3' C4' 119.49(17) . . ? C3' C2' N1' 119.06(17) . . ? C3' C2' C8' 128.02(18) . . ? N1' C2' C8' 112.91(16) . . ? O1 C1 N2 123.20(17) . . ? O1 C1 N1 120.85(17) . . ? N2 C1 N1 115.92(16) . . ? C11 C10 C9 121.05(19) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? O3' C6' C7' 107.89(18) . . ? O3' C6' H6'A 110.1 . . ? C7' C6' H6'A 110.1 . . ? O3' C6' H6'B 110.1 . . ? C7' C6' H6'B 110.1 . . ? H6'A C6' H6'B 108.4 . . ? O2 C5 O3 122.01(18) . . ? O2 C5 C3 126.64(19) . . ? O3 C5 C3 111.34(17) . . ? C12 C11 C10 119.53(19) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C14 C9 C10 118.09(18) . . ? C14 C9 C4 120.78(17) . . ? C10 C9 C4 121.10(17) . . ? C2' C8' H8'A 109.5 . . ? C2' C8' H8'B 109.5 . . ? H8'A C8' H8'B 109.5 . . ? C2' C8' H8'C 109.5 . . ? H8'A C8' H8'C 109.5 . . ? H8'B C8' H8'C 109.5 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C12 C13 C14 119.1(2) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? O2' C5' O3' 122.19(18) . . ? O2' C5' C3' 127.49(19) . . ? O3' C5' C3' 110.32(16) . . ? C13 C14 C9 121.34(19) . . ? C13 C14 H14 119.3 . . ? C9 C14 H14 119.3 . . ? O3 C6 C7 111.16(18) . . ? O3 C6 H6A 109.4 . . ? C7 C6 H6A 109.4 . . ? O3 C6 H6B 109.4 . . ? C7 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C13' C14' C9' 121.4(2) . . ? C13' C14' H14' 119.3 . . ? C9' C14' H14' 119.3 . . ? C11' C12' C13' 121.08(19) . . ? C11' C12' Cl1' 119.98(17) . . ? C13' C12' Cl1' 118.94(17) . . ? C11 C12 C13 120.85(19) . . ? C11 C12 Cl1 119.77(16) . . ? C13 C12 Cl1 119.38(17) . . ? C9' C10' C11' 121.2(2) . . ? C9' C10' H10' 119.4 . . ? C11' C10' H10' 119.4 . . ? C12' C13' C14' 119.1(2) . . ? C12' C13' H13' 120.5 . . ? C14' C13' H13' 120.5 . . ? N2 C4 C3 109.10(15) . . ? N2 C4 C9 111.07(15) . . ? C3 C4 C9 113.51(16) . . ? N2 C4 H4 107.6 . . ? C3 C4 H4 107.6 . . ? C9 C4 H4 107.6 . . ? C12' C11' C10' 119.2(2) . . ? C12' C11' H11' 120.4 . . ? C10' C11' H11' 120.4 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6' C7' H7'A 109.5 . . ? C6' C7' H7'B 109.5 . . ? H7'A C7' H7'B 109.5 . . ? C6' C7' H7'C 109.5 . . ? H7'A C7' H7'C 109.5 . . ? H7'B C7' H7'C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1' N2' C4' C3' -43.2(2) . . . . ? C1' N2' C4' C9' 81.9(2) . . . . ? C4' N2' C1' O1' -158.90(16) . . . . ? C4' N2' C1' N1' 22.6(2) . . . . ? C2' N1' C1' O1' -167.96(16) . . . . ? C2' N1' C1' N2' 10.6(2) . . . . ? C5 C3 C2 N1 175.86(16) . . . . ? C4 C3 C2 N1 -5.3(3) . . . . ? C5 C3 C2 C8 -3.9(3) . . . . ? C4 C3 C2 C8 174.95(18) . . . . ? C1 N1 C2 C3 -17.8(3) . . . . ? C1 N1 C2 C8 162.02(17) . . . . ? N2' C4' C9' C10' -149.22(19) . . . . ? C3' C4' C9' C10' -27.0(3) . . . . ? N2' C4' C9' C14' 31.1(2) . . . . ? C3' C4' C9' C14' 153.31(19) . . . . ? N2' C4' C3' C2' 33.6(2) . . . . ? C9' C4' C3' C2' -89.9(2) . . . . ? N2' C4' C3' C5' -147.80(16) . . . . ? C9' C4' C3' C5' 88.7(2) . . . . ? C5' C3' C2' N1' 175.10(16) . . . . ? C4' C3' C2' N1' -6.4(3) . . . . ? C5' C3' C2' C8' -6.4(3) . . . . ? C4' C3' C2' C8' 172.17(17) . . . . ? C1' N1' C2' C3' -18.5(3) . . . . ? C1' N1' C2' C8' 162.79(16) . . . . ? C4 N2 C1 O1 -162.95(16) . . . . ? C4 N2 C1 N1 19.2(2) . . . . ? C2 N1 C1 O1 -166.76(16) . . . . ? C2 N1 C1 N2 11.1(3) . . . . ? C5' O3' C6' C7' 169.01(19) . . . . ? C6 O3 C5 O2 0.0(3) . . . . ? C6 O3 C5 C3 -179.12(16) . . . . ? C2 C3 C5 O2 7.1(3) . . . . ? C4 C3 C5 O2 -171.82(19) . . . . ? C2 C3 C5 O3 -173.90(17) . . . . ? C4 C3 C5 O3 7.2(2) . . . . ? C9 C10 C11 C12 -0.3(3) . . . . ? C11 C10 C9 C14 0.1(3) . . . . ? C11 C10 C9 C4 -177.94(19) . . . . ? C6' O3' C5' O2' 2.0(3) . . . . ? C6' O3' C5' C3' -177.56(16) . . . . ? C2' C3' C5' O2' 0.0(3) . . . . ? C4' C3' C5' O2' -178.56(19) . . . . ? C2' C3' C5' O3' 179.50(17) . . . . ? C4' C3' C5' O3' 1.0(2) . . . . ? C12 C13 C14 C9 -0.5(3) . . . . ? C10 C9 C14 C13 0.3(3) . . . . ? C4 C9 C14 C13 178.3(2) . . . . ? C5 O3 C6 C7 -78.9(2) . . . . ? C10' C9' C14' C13' 1.9(3) . . . . ? C4' C9' C14' C13' -178.42(19) . . . . ? C10 C11 C12 C13 0.1(3) . . . . ? C10 C11 C12 Cl1 179.34(16) . . . . ? C14 C13 C12 C11 0.3(3) . . . . ? C14 C13 C12 Cl1 -178.96(17) . . . . ? C14' C9' C10' C11' -1.2(3) . . . . ? C4' C9' C10' C11' 179.06(19) . . . . ? C11' C12' C13' C14' -0.9(3) . . . . ? Cl1' C12' C13' C14' 178.43(17) . . . . ? C9' C14' C13' C12' -0.8(3) . . . . ? C1 N2 C4 C3 -38.3(2) . . . . ? C1 N2 C4 C9 87.5(2) . . . . ? C2 C3 C4 N2 30.1(2) . . . . ? C5 C3 C4 N2 -151.02(16) . . . . ? C2 C3 C4 C9 -94.4(2) . . . . ? C5 C3 C4 C9 84.5(2) . . . . ? C14 C9 C4 N2 32.5(3) . . . . ? C10 C9 C4 N2 -149.56(18) . . . . ? C14 C9 C4 C3 155.86(19) . . . . ? C10 C9 C4 C3 -26.2(3) . . . . ? C13' C12' C11' C10' 1.5(3) . . . . ? Cl1' C12' C11' C10' -177.80(17) . . . . ? C9' C10' C11' C12' -0.4(3) . . . . ? #===END # Attachment '- PYOX4.cif' # CIF-file generated for O4BR in P-1 #============================================================================== data_o4br _database_code_depnum_ccdc_archive 'CCDC 761382' #TrackingRef '- PYOX4.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H15 Br N2 O3' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C14 H15 Br N2 O3' _chemical_formula_iupac ? _chemical_formula_weight 339.18 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M '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 7.5081(6) _cell_length_b 8.6307(8) _cell_length_c 12.7259(11) _cell_angle_alpha 105.102(8) _cell_angle_beta 104.686(7) _cell_angle_gamma 100.544(7) _cell_volume 742.26(12) _cell_formula_units_Z 2 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 340 _cell_measurement_theta_min 0.97 _cell_measurement_theta_max 27.98 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.18 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.518 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 2.777 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.5321 _exptl_absorpt_correction_T_max 0.6348 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Goniometer Xcalibur, detector: Eos (Nova)' _diffrn_detector_area_resol_mean 16.0839 _diffrn_orient_matrix_UB_11 0.0217354351 _diffrn_orient_matrix_UB_12 0.0189321031 _diffrn_orient_matrix_UB_13 0.0446227890 _diffrn_orient_matrix_UB_21 0.0415867610 _diffrn_orient_matrix_UB_22 0.0564623236 _diffrn_orient_matrix_UB_23 0.0023632557 _diffrn_orient_matrix_UB_31 -0.0863433129 _diffrn_orient_matrix_UB_32 0.0138444983 _diffrn_orient_matrix_UB_33 0.0031062046 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -20.00 45.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - -25.6053 37.0000 -120.0000 65 #__ type_ start__ end____ width___ exp.time_ 2 omega -83.00 -36.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - -25.6053 125.0000 35.0000 47 #__ type_ start__ end____ width___ exp.time_ 3 omega 2.00 85.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 27.4803 -125.0000 -41.0000 83 #__ type_ start__ end____ width___ exp.time_ 4 omega 2.00 100.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 27.4803 37.0000 120.0000 98 #__ type_ start__ end____ width___ exp.time_ 5 omega 34.00 104.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 27.4803 179.0000 -90.0000 70 #__ type_ start__ end____ width___ exp.time_ 6 omega -40.00 53.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 27.4803 -37.0000 -60.0000 93 #__ type_ start__ end____ width___ exp.time_ 7 omega -96.00 4.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - -25.6053 -77.0000 0.0000 100 #__ type_ start__ end____ width___ exp.time_ 8 omega -102.00 -34.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - -25.6053 179.0000 0.0000 68 #__ type_ start__ end____ width___ exp.time_ 9 omega -3.00 98.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 27.4803 77.0000 -180.0000 101 #__ type_ start__ end____ width___ exp.time_ 10 omega -3.00 98.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 27.4803 77.0000 -90.0000 101 #__ type_ start__ end____ width___ exp.time_ 11 omega 2.00 85.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 27.4803 -125.0000 -41.0000 83 #__ type_ start__ end____ width___ exp.time_ 12 omega -102.00 -34.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - -25.6053 179.0000 -60.0000 68 #__ type_ start__ end____ width___ exp.time_ 13 omega -102.00 -34.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - -25.6053 179.0000 60.0000 68 #__ type_ start__ end____ width___ exp.time_ 14 omega -51.00 47.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - -25.6053 37.0000 60.0000 98 #__ type_ start__ end____ width___ exp.time_ 15 omega -3.00 41.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 27.4803 77.0000 -30.0000 44 #__ type_ start__ end____ width___ exp.time_ 16 omega 2.00 100.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 27.4803 37.0000 150.0000 98 ; _diffrn_measurement_method '\w scans' # number of measured reflections (redundant set) _diffrn_reflns_number 15967 _diffrn_reflns_av_R_equivalents 0.0869 _diffrn_reflns_av_sigmaI/netI 0.0827 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.31 _diffrn_reflns_theta_max 25.99 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 2908 # number of observed reflections (> n sig(I)) _reflns_number_gt 1371 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (2009) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0919P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2908 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1296 _refine_ls_R_factor_gt 0.0615 _refine_ls_wR_factor_ref 0.1640 _refine_ls_wR_factor_gt 0.1467 _refine_ls_goodness_of_fit_ref 0.872 _refine_ls_restrained_S_all 0.872 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.570 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.083 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT 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 Br1 Br -1.30389(11) -1.07053(10) 2.69737(5) 0.1117(4) Uani 1 1 d . . . N1 N -1.3995(5) -1.1525(4) 2.0545(3) 0.0474(9) Uani 1 1 d . B . H1N H -1.3674 -1.0711 2.0299 0.057 Uiso 1 1 calc R . . O1 O -1.6829(4) -1.0957(4) 2.0462(3) 0.0557(8) Uani 1 1 d . . . N2 N -1.6131(5) -1.3021(4) 2.1157(3) 0.0472(9) Uani 1 1 d . . . H2N H -1.7307 -1.3406 2.1092 0.057 Uiso 1 1 calc R . . O2 O -1.0060(4) -1.4325(4) 2.1492(3) 0.0655(9) Uani 1 1 d . B . O3 O -1.2349(5) -1.5663(4) 2.2013(3) 0.0693(10) Uani 1 1 d . B . C3 C -1.3018(5) -1.3555(5) 2.1310(3) 0.0419(10) Uani 1 1 d . B . C1 C -1.5729(6) -1.1798(6) 2.0720(4) 0.0437(10) Uani 1 1 d . . . C4 C -1.4727(5) -1.3762(5) 2.1738(3) 0.0414(10) Uani 1 1 d . . . H4 H -1.5321 -1.4957 2.1525 0.050 Uiso 1 1 calc R . . C6 C -1.1076(9) -1.6612(8) 2.2418(6) 0.094(2) Uani 1 1 d . . . H6A H -1.1745 -1.7787 2.2120 0.112 Uiso 1 1 calc R A 1 H6B H -0.9994 -1.6460 2.2135 0.112 Uiso 1 1 calc R A 1 C5 C -1.1621(7) -1.4505(6) 2.1594(4) 0.0502(11) Uani 1 1 d . . . C2 C -1.2716(5) -1.2474(5) 2.0737(4) 0.0434(10) Uani 1 1 d . . . C9 C -1.4246(6) -1.3006(6) 2.3026(4) 0.0454(11) Uani 1 1 d . . . C8 C -1.1159(6) -1.2172(6) 2.0236(4) 0.0577(13) Uani 1 1 d . B . H8A H -1.0864 -1.3202 1.9939 0.087 Uiso 1 1 calc R . . H8B H -1.0045 -1.1393 2.0818 0.087 Uiso 1 1 calc R . . H8C H -1.1560 -1.1726 1.9626 0.087 Uiso 1 1 calc R . . C14 C -1.2922(8) -1.1551(7) 2.3636(4) 0.0715(14) Uani 1 1 d . . . H14 H -1.2231 -1.1000 2.3267 0.086 Uiso 1 1 calc R . . C12 C -1.3567(9) -1.1645(8) 2.5354(4) 0.0703(15) Uani 1 1 d . . . C10 C -1.5233(8) -1.3762(7) 2.3605(5) 0.0860(18) Uani 1 1 d . . . H10 H -1.6138 -1.4780 2.3211 0.103 Uiso 1 1 calc R . . C11 C -1.4912(10) -1.3043(9) 2.4760(5) 0.096(2) Uani 1 1 d . . . H11 H -1.5652 -1.3550 2.5126 0.115 Uiso 1 1 calc R . . C13 C -1.2563(8) -1.0848(8) 2.4828(5) 0.0859(17) Uani 1 1 d . . . H13 H -1.1642 -0.9844 2.5242 0.103 Uiso 1 1 calc R . . C7B C -1.044(3) -1.612(3) 2.359(2) 0.119(5) Uani 0.428(12) 1 d P B 1 H7B1 H -0.9539 -1.5040 2.3876 0.179 Uiso 0.428(12) 1 calc PR B 1 H7B2 H -0.9838 -1.6904 2.3833 0.179 Uiso 0.428(12) 1 calc PR B 1 H7B3 H -1.1504 -1.6051 2.3870 0.179 Uiso 0.428(12) 1 calc PR B 1 C7A C -1.165(2) -1.728(2) 2.3251(14) 0.119(5) Uani 0.572(12) 1 d P B 2 H7A1 H -1.0731 -1.7823 2.3557 0.179 Uiso 0.572(12) 1 calc PR B 2 H7A2 H -1.2880 -1.8074 2.2886 0.179 Uiso 0.572(12) 1 calc PR B 2 H7A3 H -1.1720 -1.6393 2.3863 0.179 Uiso 0.572(12) 1 calc PR B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.1347(7) 0.1549(8) 0.0516(4) 0.0201(4) 0.0275(4) 0.0751(5) N1 0.040(2) 0.056(2) 0.069(2) 0.039(2) 0.0311(18) 0.0211(18) O1 0.0433(17) 0.075(2) 0.076(2) 0.0475(19) 0.0318(16) 0.0294(17) N2 0.0351(19) 0.057(2) 0.060(2) 0.031(2) 0.0198(17) 0.0130(17) O2 0.053(2) 0.086(2) 0.085(2) 0.044(2) 0.0354(18) 0.0410(18) O3 0.073(2) 0.080(2) 0.095(3) 0.058(2) 0.046(2) 0.046(2) C3 0.041(2) 0.046(3) 0.046(2) 0.018(2) 0.018(2) 0.018(2) C1 0.039(3) 0.054(3) 0.043(2) 0.018(2) 0.015(2) 0.014(2) C4 0.039(2) 0.045(3) 0.046(2) 0.021(2) 0.016(2) 0.011(2) C6 0.119(5) 0.121(5) 0.103(5) 0.080(5) 0.063(4) 0.077(4) C5 0.059(3) 0.057(3) 0.046(3) 0.024(2) 0.021(2) 0.028(3) C2 0.035(2) 0.050(3) 0.048(3) 0.018(2) 0.014(2) 0.015(2) C9 0.040(3) 0.056(3) 0.047(3) 0.023(3) 0.016(2) 0.019(2) C8 0.047(3) 0.072(3) 0.076(3) 0.040(3) 0.032(3) 0.025(2) C14 0.069(3) 0.076(4) 0.051(3) 0.007(3) 0.020(3) -0.004(3) C12 0.082(4) 0.101(5) 0.039(3) 0.021(3) 0.025(3) 0.045(4) C10 0.094(4) 0.087(4) 0.067(4) 0.018(3) 0.039(3) -0.011(3) C11 0.110(5) 0.112(5) 0.057(4) 0.020(4) 0.044(4) -0.003(4) C13 0.071(4) 0.098(5) 0.060(4) 0.003(3) 0.009(3) 0.003(3) C7B 0.109(11) 0.169(16) 0.164(13) 0.127(14) 0.077(11) 0.083(10) C7A 0.109(11) 0.169(16) 0.164(13) 0.127(14) 0.077(11) 0.083(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C12 1.914(5) . ? N1 C1 1.364(5) . ? N1 C2 1.388(5) . ? N1 H1N 0.8600 . ? O1 C1 1.234(5) . ? N2 C1 1.337(5) . ? N2 C4 1.471(5) . ? N2 H2N 0.8600 . ? O2 C5 1.199(5) . ? O3 C5 1.345(5) . ? O3 C6 1.451(6) . ? C3 C2 1.347(5) . ? C3 C5 1.477(6) . ? C3 C4 1.515(5) . ? C4 C9 1.516(6) . ? C4 H4 0.9800 . ? C6 C7B 1.36(2) . ? C6 C7A 1.451(14) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C2 C8 1.481(5) . ? C9 C14 1.346(7) . ? C9 C10 1.366(6) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C14 C13 1.412(7) . ? C14 H14 0.9300 . ? C12 C11 1.319(8) . ? C12 C13 1.340(7) . ? C10 C11 1.377(8) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C13 H13 0.9300 . ? C7B H7B1 0.9600 . ? C7B H7B2 0.9600 . ? C7B H7B3 0.9600 . ? C7A H7A1 0.9600 . ? C7A H7A2 0.9600 . ? C7A H7A3 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 124.3(3) . . ? C1 N1 H1N 117.9 . . ? C2 N1 H1N 117.9 . . ? C1 N2 C4 125.4(3) . . ? C1 N2 H2N 117.3 . . ? C4 N2 H2N 117.3 . . ? C5 O3 C6 116.0(4) . . ? C2 C3 C5 120.4(4) . . ? C2 C3 C4 121.4(3) . . ? C5 C3 C4 118.1(4) . . ? O1 C1 N2 124.0(4) . . ? O1 C1 N1 120.1(4) . . ? N2 C1 N1 115.9(4) . . ? N2 C4 C3 109.1(3) . . ? N2 C4 C9 109.2(3) . . ? C3 C4 C9 114.3(3) . . ? N2 C4 H4 108.0 . . ? C3 C4 H4 108.0 . . ? C9 C4 H4 108.0 . . ? C7B C6 C7A 47.0(9) . . ? C7B C6 O3 110.8(9) . . ? C7A C6 O3 110.8(6) . . ? C7B C6 H6A 109.5 . . ? C7A C6 H6A 65.5 . . ? O3 C6 H6A 109.5 . . ? C7B C6 H6B 109.5 . . ? C7A C6 H6B 138.9 . . ? O3 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? O2 C5 O3 122.5(4) . . ? O2 C5 C3 127.9(4) . . ? O3 C5 C3 109.6(4) . . ? C3 C2 N1 119.0(3) . . ? C3 C2 C8 127.7(3) . . ? N1 C2 C8 113.3(3) . . ? C14 C9 C10 117.3(5) . . ? C14 C9 C4 122.5(4) . . ? C10 C9 C4 120.1(5) . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C9 C14 C13 121.1(5) . . ? C9 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C11 C12 C13 120.4(5) . . ? C11 C12 Br1 120.7(5) . . ? C13 C12 Br1 118.9(5) . . ? C9 C10 C11 121.2(6) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C12 C11 C10 120.7(5) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C12 C13 C14 119.2(6) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C6 C7B H7B1 109.5 . . ? C6 C7B H7B2 109.5 . . ? C6 C7B H7B3 109.5 . . ? C6 C7A H7A1 109.5 . . ? C6 C7A H7A2 109.5 . . ? H7A1 C7A H7A2 109.5 . . ? C6 C7A H7A3 109.5 . . ? H7A1 C7A H7A3 109.5 . . ? H7A2 C7A H7A3 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N2 C1 O1 -163.8(4) . . . . ? C4 N2 C1 N1 17.4(6) . . . . ? C2 N1 C1 O1 -175.6(4) . . . . ? C2 N1 C1 N2 3.3(6) . . . . ? C1 N2 C4 C3 -25.9(6) . . . . ? C1 N2 C4 C9 99.7(5) . . . . ? C2 C3 C4 N2 15.8(6) . . . . ? C5 C3 C4 N2 -167.6(4) . . . . ? C2 C3 C4 C9 -106.8(5) . . . . ? C5 C3 C4 C9 69.9(5) . . . . ? C5 O3 C6 C7B 105.8(12) . . . . ? C5 O3 C6 C7A 156.3(10) . . . . ? C6 O3 C5 O2 4.4(7) . . . . ? C6 O3 C5 C3 -175.3(4) . . . . ? C2 C3 C5 O2 9.1(7) . . . . ? C4 C3 C5 O2 -167.5(4) . . . . ? C2 C3 C5 O3 -171.2(4) . . . . ? C4 C3 C5 O3 12.1(6) . . . . ? C5 C3 C2 N1 -176.0(4) . . . . ? C4 C3 C2 N1 0.5(6) . . . . ? C5 C3 C2 C8 5.6(7) . . . . ? C4 C3 C2 C8 -177.9(4) . . . . ? C1 N1 C2 C3 -11.8(7) . . . . ? C1 N1 C2 C8 166.8(4) . . . . ? N2 C4 C9 C14 -84.0(5) . . . . ? C3 C4 C9 C14 38.5(6) . . . . ? N2 C4 C9 C10 92.8(5) . . . . ? C3 C4 C9 C10 -144.7(4) . . . . ? C10 C9 C14 C13 0.5(7) . . . . ? C4 C9 C14 C13 177.4(4) . . . . ? C14 C9 C10 C11 1.4(8) . . . . ? C4 C9 C10 C11 -175.6(5) . . . . ? C13 C12 C11 C10 3.9(10) . . . . ? Br1 C12 C11 C10 -176.9(5) . . . . ? C9 C10 C11 C12 -3.6(10) . . . . ? C11 C12 C13 C14 -2.0(9) . . . . ? Br1 C12 C13 C14 178.8(4) . . . . ? C9 C14 C13 C12 -0.2(8) . . . . ? #===END #=============================================================================== data_lt04me _database_code_depnum_ccdc_archive 'CCDC 761383' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H18 N2 O3' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C15 H18 N2 O3' _chemical_formula_iupac ? _chemical_formula_weight 274.31 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z _cell_length_a 12.7835(6) _cell_length_b 7.3412(3) _cell_length_c 29.5499(14) _cell_angle_alpha 90 _cell_angle_beta 93.462(4) _cell_angle_gamma 90 _cell_volume 2768.1(2) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 440 _cell_measurement_theta_min 0.98 _cell_measurement_theta_max 27.89 _cell_special_details ; ; _exptl_crystal_description Cylidrical _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.18 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.9657 _exptl_absorpt_correction_T_max 0.9835 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Goniometer Xcalibur, detector: Eos (Nova)' _diffrn_detector_area_resol_mean 16.0839 _diffrn_orient_matrix_UB_11 -0.0339866112 _diffrn_orient_matrix_UB_12 -0.0181267026 _diffrn_orient_matrix_UB_13 -0.0193269167 _diffrn_orient_matrix_UB_21 0.0432244138 _diffrn_orient_matrix_UB_22 -0.0292353236 _diffrn_orient_matrix_UB_23 -0.0120302659 _diffrn_orient_matrix_UB_31 -0.0071424206 _diffrn_orient_matrix_UB_32 -0.0903056132 _diffrn_orient_matrix_UB_33 0.0077974618 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -81.00 7.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - -17.0427 -37.0000 -90.0000 88 #__ type_ start__ end____ width___ exp.time_ 2 omega -78.00 -35.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - -17.0427 179.0000 -30.0000 43 #__ type_ start__ end____ width___ exp.time_ 3 omega -62.00 -34.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - -17.0427 179.0000 120.0000 28 #__ type_ start__ end____ width___ exp.time_ 4 omega -17.00 26.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 18.9177 -99.0000 -84.0000 43 #__ type_ start__ end____ width___ exp.time_ 5 omega -1.00 89.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 18.9177 77.0000 30.0000 90 #__ type_ start__ end____ width___ exp.time_ 6 omega -59.00 11.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - -17.0427 99.0000 -95.0000 70 #__ type_ start__ end____ width___ exp.time_ 7 omega -7.00 91.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 18.9177 37.0000 -150.0000 98 #__ type_ start__ end____ width___ exp.time_ 8 omega -54.00 51.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 18.9177 -27.0000 40.0000 105 ; _diffrn_measurement_method '\w scans' # number of measured reflections (redundant set) _diffrn_reflns_number 28107 _diffrn_reflns_av_R_equivalents 0.0919 _diffrn_reflns_av_sigmaI/netI 0.0838 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 26.00 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 5424 # number of observed reflections (> n sig(I)) _reflns_number_gt 3143 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (2009) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0729P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5424 _refine_ls_number_parameters 367 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1117 _refine_ls_R_factor_gt 0.0580 _refine_ls_wR_factor_ref 0.1452 _refine_ls_wR_factor_gt 0.1323 _refine_ls_goodness_of_fit_ref 0.951 _refine_ls_restrained_S_all 0.951 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.314 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.054 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT 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 0.64543(12) 0.5821(2) 0.21267(5) 0.0189(4) Uani 1 1 d . . . N1 N 0.61339(14) -0.0760(3) 0.16224(6) 0.0179(5) Uani 1 1 d . . . H1 H 0.6024 -0.1792 0.1763 0.022 Uiso 1 1 calc R . . O1 O 0.63585(11) 0.0743(2) 0.22957(5) 0.0184(4) Uani 1 1 d . . . O3' O 0.60019(13) 0.3986(2) 0.41136(5) 0.0279(4) Uani 1 1 d . . . N2' N 0.62805(14) 0.4218(3) 0.27768(6) 0.0180(5) Uani 1 1 d . . . H2' H 0.6588 0.3236 0.2677 0.022 Uiso 1 1 calc R . . C3' C 0.60326(17) 0.5824(3) 0.34776(8) 0.0173(5) Uani 1 1 d . . . N1' N 0.61702(14) 0.7334(3) 0.27780(6) 0.0176(5) Uani 1 1 d . . . H1' H 0.6072 0.8359 0.2627 0.021 Uiso 1 1 calc R . . O2 O 0.63120(15) -0.0382(2) 0.01747(6) 0.0355(5) Uani 1 1 d . . . C2 C 0.61963(17) -0.0789(3) 0.11527(8) 0.0184(6) Uani 1 1 d . . . N2 N 0.62291(14) 0.2364(3) 0.16399(6) 0.0176(5) Uani 1 1 d . . . H2 H 0.6498 0.3348 0.1771 0.021 Uiso 1 1 calc R . . C5 C 0.61925(19) 0.0887(3) 0.04294(8) 0.0233(6) Uani 1 1 d . . . O2' O 0.62131(15) 0.6983(2) 0.42376(6) 0.0377(5) Uani 1 1 d . . . C3 C 0.60752(17) 0.0781(3) 0.09186(8) 0.0181(5) Uani 1 1 d . . . O3 O 0.61413(14) 0.2627(2) 0.02833(6) 0.0321(5) Uani 1 1 d . . . C5' C 0.60987(18) 0.5732(3) 0.39740(8) 0.0227(6) Uani 1 1 d . . . C1 C 0.62372(17) 0.0808(3) 0.18752(8) 0.0167(5) Uani 1 1 d . . . C1' C 0.63024(17) 0.5757(3) 0.25374(8) 0.0167(5) Uani 1 1 d . . . C9 C 0.46093(18) 0.2866(3) 0.11575(8) 0.0184(6) Uani 1 1 d . . . C2' C 0.61848(17) 0.7387(3) 0.32487(8) 0.0177(5) Uani 1 1 d . . . C4' C 0.57528(17) 0.4135(3) 0.32036(7) 0.0171(5) Uani 1 1 d . . . H4' H 0.6026 0.3051 0.3378 0.021 Uiso 1 1 calc R . . C9' C 0.45631(18) 0.3888(3) 0.31071(8) 0.0188(6) Uani 1 1 d . . . C8' C 0.63644(19) 0.9248(3) 0.34395(8) 0.0245(6) Uani 1 1 d . . . H8'1 H 0.5702 0.9924 0.3424 0.037 Uiso 1 1 calc R . . H8'2 H 0.6876 0.9890 0.3264 0.037 Uiso 1 1 calc R . . H8'3 H 0.6633 0.9153 0.3756 0.037 Uiso 1 1 calc R . . C8 C 0.6403(2) -0.2652(3) 0.09760(8) 0.0267(6) Uani 1 1 d . . . H8A H 0.6410 -0.2610 0.0645 0.040 Uiso 1 1 calc R . . H8B H 0.5850 -0.3484 0.1063 0.040 Uiso 1 1 calc R . . H8C H 0.7083 -0.3084 0.1104 0.040 Uiso 1 1 calc R . . C10 C 0.4199(2) 0.3961(4) 0.14843(9) 0.0347(7) Uani 1 1 d . . . H10 H 0.4655 0.4462 0.1718 0.042 Uiso 1 1 calc R . . C4 C 0.57885(17) 0.2491(3) 0.11704(8) 0.0180(5) Uani 1 1 d . . . H4 H 0.6130 0.3546 0.1024 0.022 Uiso 1 1 calc R . . C13' C 0.2777(2) 0.4243(4) 0.33083(10) 0.0379(7) Uani 1 1 d . . . H13' H 0.2301 0.4656 0.3521 0.045 Uiso 1 1 calc R . . C14 C 0.39188(19) 0.2184(3) 0.08187(8) 0.0254(6) Uani 1 1 d . . . H14 H 0.4173 0.1440 0.0586 0.031 Uiso 1 1 calc R . . C12' C 0.23926(19) 0.3436(4) 0.29159(10) 0.0296(7) Uani 1 1 d . . . C6' C 0.6006(2) 0.3714(4) 0.46001(9) 0.0371(7) Uani 1 1 d . . . H6'1 H 0.5519 0.4583 0.4734 0.045 Uiso 1 1 calc R . . H6'2 H 0.6718 0.3924 0.4741 0.045 Uiso 1 1 calc R . . C10' C 0.41719(19) 0.3040(4) 0.27162(9) 0.0315(7) Uani 1 1 d . . . H10' H 0.4647 0.2596 0.2507 0.038 Uiso 1 1 calc R . . C13 C 0.2854(2) 0.2588(4) 0.08182(9) 0.0314(7) Uani 1 1 d . . . H13 H 0.2393 0.2101 0.0584 0.038 Uiso 1 1 calc R . . C14' C 0.38464(19) 0.4475(4) 0.34051(9) 0.0322(7) Uani 1 1 d . . . H14' H 0.4086 0.5047 0.3681 0.039 Uiso 1 1 calc R . . C6 C 0.6227(2) 0.2903(4) -0.02028(9) 0.0387(8) Uani 1 1 d . . . H6A H 0.5948 0.4121 -0.0289 0.046 Uiso 1 1 calc R . . H6B H 0.5799 0.1978 -0.0373 0.046 Uiso 1 1 calc R . . C12 C 0.24495(19) 0.3664(4) 0.11441(9) 0.0277(6) Uani 1 1 d . . . C11 C 0.3145(2) 0.4340(4) 0.14784(9) 0.0373(7) Uani 1 1 d . . . H11 H 0.2889 0.5084 0.1710 0.045 Uiso 1 1 calc R . . C11' C 0.3106(2) 0.2817(4) 0.26207(9) 0.0338(7) Uani 1 1 d . . . H11' H 0.2864 0.2229 0.2348 0.041 Uiso 1 1 calc R . . C15 C 0.13018(19) 0.4096(4) 0.11508(10) 0.0404(8) Uani 1 1 d . . . H15A H 0.0930 0.3572 0.0882 0.061 Uiso 1 1 calc R . . H15B H 0.1204 0.5420 0.1150 0.061 Uiso 1 1 calc R . . H15C H 0.1023 0.3578 0.1424 0.061 Uiso 1 1 calc R . . C15' C 0.1231(2) 0.3230(4) 0.28003(11) 0.0445(8) Uani 1 1 d . . . H15D H 0.0985 0.4242 0.2606 0.067 Uiso 1 1 calc R . . H15E H 0.0856 0.3237 0.3080 0.067 Uiso 1 1 calc R . . H15F H 0.1100 0.2075 0.2640 0.067 Uiso 1 1 calc R . . C7 C 0.7329(2) 0.2764(5) -0.03267(11) 0.0554(9) Uani 1 1 d . . . H7A H 0.7761 0.3630 -0.0146 0.083 Uiso 1 1 calc R . . H7B H 0.7370 0.3046 -0.0649 0.083 Uiso 1 1 calc R . . H7C H 0.7586 0.1524 -0.0267 0.083 Uiso 1 1 calc R . . C7' C 0.5674(3) 0.1836(5) 0.46834(11) 0.0718(12) Uani 1 1 d . . . H7'1 H 0.4958 0.1655 0.4553 0.108 Uiso 1 1 calc R . . H7'2 H 0.5693 0.1611 0.5011 0.108 Uiso 1 1 calc R . . H7'3 H 0.6148 0.0987 0.4542 0.108 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1' 0.0244(9) 0.0171(10) 0.0153(9) -0.0009(7) 0.0025(7) 0.0000(7) N1 0.0260(11) 0.0096(11) 0.0185(11) 0.0005(9) 0.0038(8) -0.0032(9) O1 0.0250(9) 0.0154(9) 0.0146(9) -0.0007(7) 0.0001(7) 0.0013(7) O3' 0.0415(11) 0.0266(11) 0.0154(9) 0.0030(8) 0.0016(8) -0.0074(9) N2' 0.0196(11) 0.0130(11) 0.0220(12) 0.0000(9) 0.0058(8) 0.0026(9) C3' 0.0165(12) 0.0152(13) 0.0201(13) -0.0027(11) 0.0003(10) -0.0021(10) N1' 0.0242(11) 0.0113(11) 0.0172(11) 0.0018(9) 0.0001(8) 0.0028(9) O2 0.0587(13) 0.0256(11) 0.0227(11) -0.0043(9) 0.0069(9) 0.0040(9) C2 0.0177(13) 0.0193(14) 0.0181(13) -0.0004(11) 0.0014(10) -0.0013(11) N2 0.0213(11) 0.0108(11) 0.0201(11) -0.0009(9) -0.0034(8) -0.0038(9) C5 0.0289(14) 0.0189(15) 0.0222(14) 0.0008(13) 0.0023(11) 0.0014(12) O2' 0.0658(14) 0.0240(11) 0.0229(11) -0.0052(9) 0.0007(9) -0.0015(10) C3 0.0191(13) 0.0153(14) 0.0200(13) -0.0006(11) 0.0022(10) -0.0019(11) O3 0.0526(12) 0.0219(11) 0.0224(10) 0.0073(8) 0.0081(8) 0.0027(9) C5' 0.0239(14) 0.0203(15) 0.0240(15) -0.0023(13) 0.0010(11) -0.0008(12) C1 0.0122(12) 0.0155(14) 0.0224(14) 0.0000(12) 0.0017(10) 0.0013(10) C1' 0.0138(12) 0.0171(14) 0.0190(14) -0.0016(12) -0.0002(9) 0.0005(10) C9 0.0230(13) 0.0153(13) 0.0169(13) 0.0021(11) 0.0003(10) 0.0020(11) C2' 0.0154(13) 0.0169(14) 0.0207(14) -0.0039(11) 0.0006(10) 0.0007(11) C4' 0.0224(13) 0.0130(13) 0.0162(13) 0.0004(10) 0.0033(10) -0.0019(11) C9' 0.0211(13) 0.0118(13) 0.0237(14) 0.0001(11) 0.0030(10) 0.0005(10) C8' 0.0284(14) 0.0176(14) 0.0284(15) -0.0067(12) 0.0084(11) -0.0067(12) C8 0.0414(17) 0.0171(15) 0.0218(14) -0.0013(12) 0.0033(12) 0.0038(12) C10 0.0309(16) 0.0405(18) 0.0316(16) -0.0153(14) -0.0079(12) 0.0081(13) C4 0.0241(14) 0.0152(13) 0.0148(13) 0.0005(11) 0.0007(10) -0.0020(11) C13' 0.0250(16) 0.0414(19) 0.0487(19) -0.0106(16) 0.0146(13) -0.0021(14) C14 0.0305(15) 0.0246(15) 0.0210(14) -0.0053(12) -0.0007(11) 0.0032(12) C12' 0.0234(15) 0.0230(15) 0.0424(18) -0.0031(14) 0.0020(13) -0.0038(12) C6' 0.0533(19) 0.0420(19) 0.0161(15) 0.0056(13) 0.0017(13) -0.0047(15) C10' 0.0238(15) 0.0393(18) 0.0321(16) -0.0101(14) 0.0062(12) -0.0033(13) C13 0.0278(16) 0.0345(17) 0.0304(16) -0.0003(14) -0.0103(12) -0.0015(13) C14' 0.0263(15) 0.0362(17) 0.0346(17) -0.0117(14) 0.0042(12) -0.0040(13) C6 0.062(2) 0.0316(17) 0.0232(16) 0.0081(13) 0.0111(14) 0.0040(15) C12 0.0238(15) 0.0275(16) 0.0313(16) 0.0040(13) -0.0018(12) 0.0033(12) C11 0.0328(17) 0.0446(19) 0.0344(17) -0.0131(15) 0.0004(13) 0.0130(14) C11' 0.0305(16) 0.0383(18) 0.0320(16) -0.0125(14) -0.0035(12) -0.0101(13) C15 0.0239(15) 0.0394(19) 0.058(2) 0.0035(16) -0.0012(13) 0.0039(14) C15' 0.0286(17) 0.040(2) 0.064(2) -0.0013(17) -0.0005(15) -0.0027(14) C7 0.067(2) 0.058(2) 0.042(2) 0.0186(18) 0.0108(17) -0.0037(19) C7' 0.126(3) 0.060(2) 0.0273(19) 0.0148(18) -0.005(2) -0.047(2) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1' C1' 1.242(3) . ? N1 C1 1.374(3) . ? N1 C2 1.395(3) . ? N1 H1 0.8800 . ? O1 C1 1.244(3) . ? O3' C5' 1.355(3) . ? O3' C6' 1.451(3) . ? N2' C1' 1.335(3) . ? N2' C4' 1.467(3) . ? N2' H2' 0.8800 . ? C3' C2' 1.352(3) . ? C3' C5' 1.466(3) . ? C3' C4' 1.512(3) . ? N1' C1' 1.374(3) . ? N1' C2' 1.390(3) . ? N1' H1' 0.8800 . ? O2 C5 1.213(3) . ? C2 C3 1.349(3) . ? C2 C8 1.493(3) . ? N2 C1 1.337(3) . ? N2 C4 1.468(3) . ? N2 H2 0.8800 . ? C5 O3 1.349(3) . ? C5 C3 1.464(3) . ? O2' C5' 1.207(3) . ? C3 C4 1.515(3) . ? O3 C6 1.461(3) . ? C9 C10 1.384(3) . ? C9 C14 1.388(3) . ? C9 C4 1.531(3) . ? C2' C8' 1.490(3) . ? C4' C9' 1.541(3) . ? C4' H4' 1.0000 . ? C9' C14' 1.378(3) . ? C9' C10' 1.379(3) . ? C8' H8'1 0.9800 . ? C8' H8'2 0.9800 . ? C8' H8'3 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C10 C11 1.375(3) . ? C10 H10 0.9500 . ? C4 H4 1.0000 . ? C13' C12' 1.367(4) . ? C13' C14' 1.390(3) . ? C13' H13' 0.9500 . ? C14 C13 1.393(3) . ? C14 H14 0.9500 . ? C12' C11' 1.377(4) . ? C12' C15' 1.511(3) . ? C6' C7' 1.468(4) . ? C6' H6'1 0.9900 . ? C6' H6'2 0.9900 . ? C10' C11' 1.384(3) . ? C10' H10' 0.9500 . ? C13 C12 1.371(4) . ? C13 H13 0.9500 . ? C14' H14' 0.9500 . ? C6 C7 1.481(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C12 C11 1.380(4) . ? C12 C15 1.502(3) . ? C11 H11 0.9500 . ? C11' H11' 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C15' H15D 0.9800 . ? C15' H15E 0.9800 . ? C15' H15F 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C7' H7'1 0.9800 . ? C7' H7'2 0.9800 . ? C7' H7'3 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 122.96(19) . . ? C1 N1 H1 118.5 . . ? C2 N1 H1 118.5 . . ? C5' O3' C6' 115.91(19) . . ? C1' N2' C4' 121.07(19) . . ? C1' N2' H2' 119.5 . . ? C4' N2' H2' 119.5 . . ? C2' C3' C5' 122.6(2) . . ? C2' C3' C4' 117.7(2) . . ? C5' C3' C4' 119.7(2) . . ? C1' N1' C2' 123.1(2) . . ? C1' N1' H1' 118.4 . . ? C2' N1' H1' 118.4 . . ? C3 C2 N1 119.0(2) . . ? C3 C2 C8 128.4(2) . . ? N1 C2 C8 112.6(2) . . ? C1 N2 C4 122.40(19) . . ? C1 N2 H2 118.8 . . ? C4 N2 H2 118.8 . . ? O2 C5 O3 122.3(2) . . ? O2 C5 C3 126.6(2) . . ? O3 C5 C3 111.1(2) . . ? C2 C3 C5 122.4(2) . . ? C2 C3 C4 118.7(2) . . ? C5 C3 C4 118.9(2) . . ? C5 O3 C6 116.2(2) . . ? O2' C5' O3' 122.2(2) . . ? O2' C5' C3' 127.4(2) . . ? O3' C5' C3' 110.3(2) . . ? O1 C1 N2 123.3(2) . . ? O1 C1 N1 120.8(2) . . ? N2 C1 N1 115.8(2) . . ? O1' C1' N2' 124.0(2) . . ? O1' C1' N1' 120.4(2) . . ? N2' C1' N1' 115.6(2) . . ? C10 C9 C14 117.5(2) . . ? C10 C9 C4 120.1(2) . . ? C14 C9 C4 122.4(2) . . ? C3' C2' N1' 118.9(2) . . ? C3' C2' C8' 127.7(2) . . ? N1' C2' C8' 113.4(2) . . ? N2' C4' C3' 108.68(18) . . ? N2' C4' C9' 110.22(18) . . ? C3' C4' C9' 113.24(18) . . ? N2' C4' H4' 108.2 . . ? C3' C4' H4' 108.2 . . ? C9' C4' H4' 108.2 . . ? C14' C9' C10' 117.1(2) . . ? C14' C9' C4' 122.1(2) . . ? C10' C9' C4' 120.8(2) . . ? C2' C8' H8'1 109.5 . . ? C2' C8' H8'2 109.5 . . ? H8'1 C8' H8'2 109.5 . . ? C2' C8' H8'3 109.5 . . ? H8'1 C8' H8'3 109.5 . . ? H8'2 C8' H8'3 109.5 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C11 C10 C9 121.4(2) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? N2 C4 C3 108.73(18) . . ? N2 C4 C9 110.85(18) . . ? C3 C4 C9 113.83(18) . . ? N2 C4 H4 107.7 . . ? C3 C4 H4 107.7 . . ? C9 C4 H4 107.7 . . ? C12' C13' C14' 121.8(3) . . ? C12' C13' H13' 119.1 . . ? C14' C13' H13' 119.1 . . ? C9 C14 C13 120.2(2) . . ? C9 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C13' C12' C11' 117.5(2) . . ? C13' C12' C15' 122.3(2) . . ? C11' C12' C15' 120.2(3) . . ? O3' C6' C7' 108.2(2) . . ? O3' C6' H6'1 110.1 . . ? C7' C6' H6'1 110.1 . . ? O3' C6' H6'2 110.1 . . ? C7' C6' H6'2 110.1 . . ? H6'1 C6' H6'2 108.4 . . ? C9' C10' C11' 121.8(2) . . ? C9' C10' H10' 119.1 . . ? C11' C10' H10' 119.1 . . ? C12 C13 C14 122.1(2) . . ? C12 C13 H13 119.0 . . ? C14 C13 H13 119.0 . . ? C9' C14' C13' 120.9(3) . . ? C9' C14' H14' 119.5 . . ? C13' C14' H14' 119.5 . . ? O3 C6 C7 111.2(2) . . ? O3 C6 H6A 109.4 . . ? C7 C6 H6A 109.4 . . ? O3 C6 H6B 109.4 . . ? C7 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C13 C12 C11 117.1(2) . . ? C13 C12 C15 122.7(2) . . ? C11 C12 C15 120.1(2) . . ? C10 C11 C12 121.7(3) . . ? C10 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? C12' C11' C10' 120.9(3) . . ? C12' C11' H11' 119.6 . . ? C10' C11' H11' 119.6 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C12' C15' H15D 109.5 . . ? C12' C15' H15E 109.5 . . ? H15D C15' H15E 109.5 . . ? C12' C15' H15F 109.5 . . ? H15D C15' H15F 109.5 . . ? H15E C15' H15F 109.5 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6' C7' H7'1 109.5 . . ? C6' C7' H7'2 109.5 . . ? H7'1 C7' H7'2 109.5 . . ? C6' C7' H7'3 109.5 . . ? H7'1 C7' H7'3 109.5 . . ? H7'2 C7' H7'3 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 C2 C3 -18.1(3) . . . . ? C1 N1 C2 C8 161.6(2) . . . . ? N1 C2 C3 C5 176.2(2) . . . . ? C8 C2 C3 C5 -3.5(4) . . . . ? N1 C2 C3 C4 -4.9(3) . . . . ? C8 C2 C3 C4 175.4(2) . . . . ? O2 C5 C3 C2 7.0(4) . . . . ? O3 C5 C3 C2 -173.6(2) . . . . ? O2 C5 C3 C4 -171.9(2) . . . . ? O3 C5 C3 C4 7.5(3) . . . . ? O2 C5 O3 C6 0.6(4) . . . . ? C3 C5 O3 C6 -178.8(2) . . . . ? C6' O3' C5' O2' 2.2(3) . . . . ? C6' O3' C5' C3' -177.28(19) . . . . ? C2' C3' C5' O2' 5.8(4) . . . . ? C4' C3' C5' O2' -172.4(2) . . . . ? C2' C3' C5' O3' -174.8(2) . . . . ? C4' C3' C5' O3' 7.0(3) . . . . ? C4 N2 C1 O1 -161.6(2) . . . . ? C4 N2 C1 N1 20.3(3) . . . . ? C2 N1 C1 O1 -167.44(19) . . . . ? C2 N1 C1 N2 10.7(3) . . . . ? C4' N2' C1' O1' -158.5(2) . . . . ? C4' N2' C1' N1' 23.2(3) . . . . ? C2' N1' C1' O1' -168.14(19) . . . . ? C2' N1' C1' N2' 10.3(3) . . . . ? C5' C3' C2' N1' 176.2(2) . . . . ? C4' C3' C2' N1' -5.7(3) . . . . ? C5' C3' C2' C8' -4.5(4) . . . . ? C4' C3' C2' C8' 173.7(2) . . . . ? C1' N1' C2' C3' -18.8(3) . . . . ? C1' N1' C2' C8' 161.7(2) . . . . ? C1' N2' C4' C3' -43.6(3) . . . . ? C1' N2' C4' C9' 81.1(2) . . . . ? C2' C3' C4' N2' 33.2(3) . . . . ? C5' C3' C4' N2' -148.5(2) . . . . ? C2' C3' C4' C9' -89.6(2) . . . . ? C5' C3' C4' C9' 88.6(3) . . . . ? N2' C4' C9' C14' -153.4(2) . . . . ? C3' C4' C9' C14' -31.5(3) . . . . ? N2' C4' C9' C10' 27.3(3) . . . . ? C3' C4' C9' C10' 149.3(2) . . . . ? C14 C9 C10 C11 1.0(4) . . . . ? C4 C9 C10 C11 179.3(2) . . . . ? C1 N2 C4 C3 -39.3(3) . . . . ? C1 N2 C4 C9 86.6(2) . . . . ? C2 C3 C4 N2 30.2(3) . . . . ? C5 C3 C4 N2 -150.9(2) . . . . ? C2 C3 C4 C9 -93.9(2) . . . . ? C5 C3 C4 C9 85.0(3) . . . . ? C10 C9 C4 N2 35.1(3) . . . . ? C14 C9 C4 N2 -146.6(2) . . . . ? C10 C9 C4 C3 158.1(2) . . . . ? C14 C9 C4 C3 -23.7(3) . . . . ? C10 C9 C14 C13 -0.8(4) . . . . ? C4 C9 C14 C13 -179.0(2) . . . . ? C14' C13' C12' C11' 1.4(4) . . . . ? C14' C13' C12' C15' -178.0(3) . . . . ? C5' O3' C6' C7' 168.2(3) . . . . ? C14' C9' C10' C11' 1.3(4) . . . . ? C4' C9' C10' C11' -179.4(2) . . . . ? C9 C14 C13 C12 0.4(4) . . . . ? C10' C9' C14' C13' -1.1(4) . . . . ? C4' C9' C14' C13' 179.7(2) . . . . ? C12' C13' C14' C9' -0.3(4) . . . . ? C5 O3 C6 C7 -77.9(3) . . . . ? C14 C13 C12 C11 -0.2(4) . . . . ? C14 C13 C12 C15 -179.4(2) . . . . ? C9 C10 C11 C12 -0.8(5) . . . . ? C13 C12 C11 C10 0.4(4) . . . . ? C15 C12 C11 C10 179.6(3) . . . . ? C13' C12' C11' C10' -1.2(4) . . . . ? C15' C12' C11' C10' 178.3(3) . . . . ? C9' C10' C11' C12' -0.2(4) . . . . ? #===END # Attachment '- PYOX6.cif' # CIF-file generated for LT04OME in P2(1)/n #============================================================================== data_lt04ome _database_code_depnum_ccdc_archive 'CCDC 761384' #TrackingRef '- PYOX6.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H18 N2 O4' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C15 H18 N2 O4' _chemical_formula_iupac ? _chemical_formula_weight 290.31 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z _cell_length_a 15.7414(10) _cell_length_b 7.3100(4) _cell_length_c 26.3147(14) _cell_angle_alpha 90 _cell_angle_beta 103.377(6) _cell_angle_gamma 90 _cell_volume 2945.9(3) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 344 _cell_measurement_theta_min 0.97 _cell_measurement_theta_max 27.98 _cell_special_details ; ; _exptl_crystal_description Cylidrical _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.14 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.309 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.9709 _exptl_absorpt_correction_T_max 0.9867 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Goniometer Xcalibur, detector: Eos (Nova)' _diffrn_detector_area_resol_mean 16.0839 _diffrn_orient_matrix_UB_11 -0.0310945448 _diffrn_orient_matrix_UB_12 0.0035386872 _diffrn_orient_matrix_UB_13 0.0156400568 _diffrn_orient_matrix_UB_21 0.0336139824 _diffrn_orient_matrix_UB_22 -0.0154553307 _diffrn_orient_matrix_UB_23 0.0226419416 _diffrn_orient_matrix_UB_31 0.0065911242 _diffrn_orient_matrix_UB_32 0.0957115208 _diffrn_orient_matrix_UB_33 0.0030886184 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -94.00 -58.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -17.1989 179.0000 -150.0000 36 #__ type_ start__ end____ width___ exp.time_ 2 omega -17.00 13.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -17.1989 -77.0000 -180.0000 30 #__ type_ start__ end____ width___ exp.time_ 3 omega -22.00 42.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 -37.0000 -60.0000 64 #__ type_ start__ end____ width___ exp.time_ 4 omega -49.00 92.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 12.0000 -16.0000 141 #__ type_ start__ end____ width___ exp.time_ 5 omega -43.00 17.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -17.1989 37.0000 -150.0000 60 #__ type_ start__ end____ width___ exp.time_ 6 omega -7.00 92.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 37.0000 120.0000 99 #__ type_ start__ end____ width___ exp.time_ 7 omega -54.00 91.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 -12.0000 -9.0000 145 ; _diffrn_measurement_method '\w scans' # number of measured reflections (redundant set) _diffrn_reflns_number 30736 _diffrn_reflns_av_R_equivalents 0.0722 _diffrn_reflns_av_sigmaI/netI 0.0696 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 26.00 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 5768 # number of observed reflections (> n sig(I)) _reflns_number_gt 3458 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (2009) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0675P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5768 _refine_ls_number_parameters 385 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0939 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1277 _refine_ls_wR_factor_gt 0.1186 _refine_ls_goodness_of_fit_ref 0.931 _refine_ls_restrained_S_all 0.931 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.320 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.051 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT 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 0.14509(9) -0.05047(16) 0.21709(5) 0.0219(3) Uani 1 1 d . . . O1' O 1.16904(9) 0.45882(17) 0.20543(5) 0.0224(3) Uani 1 1 d . . . N1 N 0.23461(11) -0.2055(2) 0.17571(6) 0.0216(4) Uani 1 1 d . . . H1N H 0.2080 -0.3088 0.1795 0.026 Uiso 1 1 calc R . . N2' N 1.05758(11) 0.2903(2) 0.22173(6) 0.0214(4) Uani 1 1 d . . . H2N' H 1.0873 0.1879 0.2225 0.026 Uiso 1 1 calc R . . N1' N 1.05660(11) 0.6029(2) 0.22992(6) 0.0216(4) Uani 1 1 d . . . H1N' H 1.0738 0.7099 0.2208 0.026 Uiso 1 1 calc R . . C3 C 0.33318(13) -0.0580(3) 0.13402(7) 0.0202(5) Uani 1 1 d . . . N2 N 0.23809(11) 0.1075(2) 0.17837(6) 0.0204(4) Uani 1 1 d . . . H2N H 0.2368 0.2072 0.1969 0.024 Uiso 1 1 calc R . . O3 O 0.42309(10) 0.1150(2) 0.09412(6) 0.0323(4) Uani 1 1 d . . . C1 C 0.20225(13) -0.0465(3) 0.19145(7) 0.0197(5) Uani 1 1 d . . . O4' O 0.71699(10) 0.3040(2) 0.02951(6) 0.0387(4) Uani 1 1 d . . . C3' C 0.94623(14) 0.4375(3) 0.25716(8) 0.0221(5) Uani 1 1 d . . . O2 O 0.45358(11) -0.1840(2) 0.10404(6) 0.0406(4) Uani 1 1 d . . . O3' O 0.85502(11) 0.2388(2) 0.28867(6) 0.0389(4) Uani 1 1 d . . . O4 O 0.01317(11) 0.2524(2) -0.04941(6) 0.0408(4) Uani 1 1 d . . . O2' O 0.85081(11) 0.5352(2) 0.31061(7) 0.0452(5) Uani 1 1 d . . . C1' C 1.09783(14) 0.4476(3) 0.21824(7) 0.0203(5) Uani 1 1 d . . . C9' C 0.90374(14) 0.2807(3) 0.17013(8) 0.0226(5) Uani 1 1 d . . . C5 C 0.40927(15) -0.0551(3) 0.11038(8) 0.0255(5) Uani 1 1 d . . . C2 C 0.30740(14) -0.2123(3) 0.15403(7) 0.0213(5) Uani 1 1 d . . . C2' C 0.98828(14) 0.5970(3) 0.25585(7) 0.0225(5) Uani 1 1 d . . . C14' C 0.92139(15) 0.3761(3) 0.12821(8) 0.0283(5) Uani 1 1 d . . . H14' H 0.9762 0.4359 0.1323 0.034 Uiso 1 1 calc R . . C5' C 0.88034(15) 0.4152(3) 0.28813(9) 0.0296(5) Uani 1 1 d . . . C4 C 0.27961(14) 0.1142(3) 0.13364(7) 0.0222(5) Uani 1 1 d . . . H4 H 0.3206 0.2207 0.1389 0.027 Uiso 1 1 calc R . . C12 C 0.07965(15) 0.2097(3) -0.00730(8) 0.0305(6) Uani 1 1 d . . . C12' C 0.78184(15) 0.3003(3) 0.07421(8) 0.0283(5) Uani 1 1 d . . . C10' C 0.82370(15) 0.1925(3) 0.16271(9) 0.0315(5) Uani 1 1 d . . . H10' H 0.8099 0.1255 0.1907 0.038 Uiso 1 1 calc R . . C13' C 0.86149(15) 0.3869(3) 0.08047(8) 0.0298(5) Uani 1 1 d . . . H13' H 0.8752 0.4533 0.0524 0.036 Uiso 1 1 calc R . . C4' C 0.96573(13) 0.2799(3) 0.22428(8) 0.0226(5) Uani 1 1 d . . . H4' H 0.9568 0.1631 0.2421 0.027 Uiso 1 1 calc R . . C14 C 0.14905(16) 0.2842(3) 0.08119(8) 0.0322(6) Uani 1 1 d . . . H14 H 0.1520 0.3589 0.1111 0.039 Uiso 1 1 calc R . . C11' C 0.76413(15) 0.2007(3) 0.11549(9) 0.0351(6) Uani 1 1 d . . . H11' H 0.7102 0.1375 0.1110 0.042 Uiso 1 1 calc R . . C9 C 0.21036(14) 0.1467(3) 0.08314(7) 0.0217(5) Uani 1 1 d . . . C8 C 0.34742(15) -0.3977(3) 0.15649(8) 0.0283(5) Uani 1 1 d . . . H8A H 0.3169 -0.4702 0.1265 0.042 Uiso 1 1 calc R . . H8B H 0.3426 -0.4586 0.1889 0.042 Uiso 1 1 calc R . . H8C H 0.4091 -0.3864 0.1557 0.042 Uiso 1 1 calc R . . C13 C 0.08416(16) 0.3156(3) 0.03721(9) 0.0365(6) Uani 1 1 d . . . H13 H 0.0424 0.4095 0.0372 0.044 Uiso 1 1 calc R . . C10 C 0.20523(16) 0.0452(3) 0.03847(8) 0.0353(6) Uani 1 1 d . . . H10 H 0.2472 -0.0480 0.0384 0.042 Uiso 1 1 calc R . . C11 C 0.14028(17) 0.0754(3) -0.00654(9) 0.0399(7) Uani 1 1 d . . . H11 H 0.1381 0.0027 -0.0367 0.048 Uiso 1 1 calc R . . C8' C 0.97309(15) 0.7754(3) 0.28023(9) 0.0311(5) Uani 1 1 d . . . H8'A H 0.9104 0.8018 0.2723 0.047 Uiso 1 1 calc R . . H8'B H 1.0036 0.8732 0.2662 0.047 Uiso 1 1 calc R . . H8'C H 0.9954 0.7679 0.3182 0.047 Uiso 1 1 calc R . . C15' C 0.72954(18) 0.4215(3) -0.01176(9) 0.0429(7) Uani 1 1 d . . . H15D H 0.7392 0.5471 0.0013 0.064 Uiso 1 1 calc R . . H15E H 0.6775 0.4176 -0.0406 0.064 Uiso 1 1 calc R . . H15F H 0.7804 0.3800 -0.0242 0.064 Uiso 1 1 calc R . . C6 C 0.49571(17) 0.1331(3) 0.06879(10) 0.0434(6) Uani 1 1 d . . . H6A H 0.4949 0.0312 0.0439 0.052 Uiso 1 1 calc R . . H6B H 0.5518 0.1291 0.0952 0.052 Uiso 1 1 calc R . . C6' C 0.78906(19) 0.1964(4) 0.31870(10) 0.0502(7) Uani 1 1 d . . . H6'A H 0.7470 0.2988 0.3155 0.060 Uiso 1 1 calc R . . H6'B H 0.7564 0.0851 0.3043 0.060 Uiso 1 1 calc R . . C15 C 0.00440(19) 0.1416(3) -0.09502(9) 0.0540(8) Uani 1 1 d . . . H15A H 0.0581 0.1488 -0.1077 0.081 Uiso 1 1 calc R . . H15B H -0.0449 0.1857 -0.1222 0.081 Uiso 1 1 calc R . . H15C H -0.0060 0.0144 -0.0864 0.081 Uiso 1 1 calc R . . C7 C 0.4869(2) 0.3102(4) 0.04070(13) 0.0699(10) Uani 1 1 d . . . H7A H 0.4331 0.3100 0.0131 0.105 Uiso 1 1 calc R . . H7B H 0.5371 0.3278 0.0251 0.105 Uiso 1 1 calc R . . H7C H 0.4848 0.4098 0.0653 0.105 Uiso 1 1 calc R . . C7' C 0.8313(2) 0.1671(4) 0.37389(12) 0.0790(11) Uani 1 1 d . . . H7'A H 0.8735 0.0668 0.3769 0.118 Uiso 1 1 calc R . . H7'B H 0.7870 0.1359 0.3932 0.118 Uiso 1 1 calc R . . H7'C H 0.8617 0.2791 0.3884 0.118 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0197(8) 0.0245(8) 0.0247(8) -0.0002(6) 0.0116(7) 0.0007(6) O1' 0.0191(8) 0.0236(8) 0.0272(8) -0.0010(6) 0.0109(6) -0.0010(6) N1 0.0223(10) 0.0174(9) 0.0282(10) -0.0019(7) 0.0122(8) -0.0017(8) N2' 0.0164(10) 0.0170(9) 0.0334(10) 0.0019(7) 0.0110(8) 0.0018(8) N1' 0.0232(10) 0.0175(9) 0.0274(9) 0.0037(7) 0.0129(8) 0.0017(8) C3 0.0190(12) 0.0228(12) 0.0206(10) -0.0004(8) 0.0082(9) 0.0016(9) N2 0.0243(10) 0.0175(9) 0.0215(9) -0.0041(7) 0.0099(8) -0.0010(8) O3 0.0267(9) 0.0370(9) 0.0397(9) 0.0080(7) 0.0208(7) 0.0005(7) C1 0.0179(12) 0.0220(12) 0.0181(10) -0.0006(8) 0.0018(9) 0.0002(9) O4' 0.0285(10) 0.0569(10) 0.0295(9) -0.0011(7) 0.0039(8) -0.0022(8) C3' 0.0195(12) 0.0244(12) 0.0243(11) 0.0024(9) 0.0087(9) 0.0039(10) O2 0.0386(11) 0.0371(10) 0.0552(11) 0.0042(8) 0.0294(9) 0.0111(8) O3' 0.0404(11) 0.0408(10) 0.0450(10) -0.0032(7) 0.0292(9) -0.0123(8) O4 0.0379(11) 0.0474(10) 0.0312(9) 0.0070(7) -0.0040(8) 0.0011(8) O2' 0.0446(12) 0.0469(10) 0.0561(11) -0.0033(8) 0.0361(10) 0.0057(9) C1' 0.0202(12) 0.0228(12) 0.0182(10) 0.0016(8) 0.0051(9) 0.0029(10) C9' 0.0211(12) 0.0210(11) 0.0283(11) -0.0024(9) 0.0112(10) 0.0014(9) C5 0.0240(13) 0.0276(13) 0.0260(12) 0.0033(9) 0.0076(10) 0.0016(10) C2 0.0186(12) 0.0265(12) 0.0196(10) -0.0004(9) 0.0061(9) 0.0019(9) C2' 0.0206(12) 0.0279(13) 0.0206(11) 0.0032(9) 0.0080(9) 0.0064(10) C14' 0.0217(13) 0.0308(12) 0.0346(13) 0.0002(10) 0.0109(10) -0.0046(10) C5' 0.0275(14) 0.0341(14) 0.0302(12) 0.0004(10) 0.0128(11) 0.0013(11) C4 0.0258(13) 0.0218(11) 0.0225(11) 0.0002(8) 0.0129(9) -0.0024(9) C12 0.0299(14) 0.0303(13) 0.0294(12) 0.0057(10) 0.0034(11) -0.0022(11) C12' 0.0240(13) 0.0358(13) 0.0270(12) -0.0053(10) 0.0098(10) 0.0019(10) C10' 0.0279(14) 0.0396(13) 0.0308(13) 0.0021(10) 0.0144(11) -0.0068(11) C13' 0.0309(14) 0.0332(13) 0.0270(12) 0.0011(9) 0.0103(11) -0.0035(11) C4' 0.0185(12) 0.0225(11) 0.0302(12) 0.0038(9) 0.0128(9) -0.0014(9) C14 0.0380(15) 0.0367(13) 0.0242(12) 0.0012(9) 0.0117(11) 0.0100(11) C11' 0.0216(13) 0.0494(15) 0.0367(14) -0.0023(11) 0.0117(11) -0.0100(11) C9 0.0234(12) 0.0216(11) 0.0228(11) 0.0032(8) 0.0107(9) 0.0006(9) C8 0.0326(14) 0.0264(12) 0.0294(12) 0.0038(9) 0.0143(10) 0.0059(10) C13 0.0331(15) 0.0458(14) 0.0321(13) 0.0049(11) 0.0108(11) 0.0158(12) C10 0.0398(16) 0.0334(13) 0.0312(13) -0.0039(10) 0.0052(11) 0.0123(11) C11 0.0534(18) 0.0337(14) 0.0278(13) -0.0059(10) -0.0005(12) 0.0083(13) C8' 0.0317(14) 0.0281(12) 0.0371(13) -0.0034(10) 0.0152(11) 0.0006(10) C15' 0.0466(17) 0.0505(15) 0.0290(13) 0.0010(11) 0.0033(12) 0.0010(13) C6 0.0327(15) 0.0546(16) 0.0526(16) 0.0119(13) 0.0298(13) 0.0035(13) C6' 0.0518(19) 0.0563(17) 0.0537(17) -0.0039(13) 0.0349(15) -0.0178(14) C15 0.066(2) 0.0462(16) 0.0373(15) -0.0006(12) -0.0144(14) -0.0061(14) C7 0.055(2) 0.071(2) 0.099(3) 0.0352(18) 0.0486(19) 0.0078(16) C7' 0.076(3) 0.102(2) 0.063(2) 0.0139(18) 0.0236(19) -0.035(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.244(2) . ? O1' C1' 1.246(2) . ? N1 C1 1.371(2) . ? N1 C2 1.394(3) . ? N1 H1N 0.8800 . ? N2' C1' 1.326(2) . ? N2' C4' 1.465(3) . ? N2' H2N' 0.8800 . ? N1' C1' 1.377(3) . ? N1' C2' 1.401(3) . ? N1' H1N' 0.8800 . ? C3 C2 1.347(3) . ? C3 C5 1.472(3) . ? C3 C4 1.514(3) . ? N2 C1 1.339(2) . ? N2 C4 1.474(2) . ? N2 H2N 0.8800 . ? O3 C5 1.349(2) . ? O3 C6 1.456(3) . ? O4' C12' 1.368(3) . ? O4' C15' 1.433(3) . ? C3' C2' 1.345(3) . ? C3' C5' 1.469(3) . ? C3' C4' 1.514(3) . ? O2 C5 1.207(2) . ? O3' C5' 1.351(3) . ? O3' C6' 1.476(3) . ? O4 C12 1.373(2) . ? O4 C15 1.428(3) . ? O2' C5' 1.209(3) . ? C9' C14' 1.386(3) . ? C9' C10' 1.388(3) . ? C9' C4' 1.529(3) . ? C2 C8 1.490(3) . ? C2' C8' 1.496(3) . ? C14' C13' 1.388(3) . ? C14' H14' 0.9500 . ? C4 C9 1.530(3) . ? C4 H4 1.0000 . ? C12 C11 1.366(3) . ? C12 C13 1.392(3) . ? C12' C13' 1.380(3) . ? C12' C11' 1.389(3) . ? C10' C11' 1.374(3) . ? C10' H10' 0.9500 . ? C13' H13' 0.9500 . ? C4' H4' 1.0000 . ? C14 C13 1.374(3) . ? C14 C9 1.386(3) . ? C14 H14 0.9500 . ? C11' H11' 0.9500 . ? C9 C10 1.377(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C13 H13 0.9500 . ? C10 C11 1.392(3) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C8' H8'A 0.9800 . ? C8' H8'B 0.9800 . ? C8' H8'C 0.9800 . ? C15' H15D 0.9800 . ? C15' H15E 0.9800 . ? C15' H15F 0.9800 . ? C6 C7 1.481(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C6' C7' 1.466(4) . ? C6' H6'A 0.9900 . ? C6' H6'B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C7' H7'A 0.9800 . ? C7' H7'B 0.9800 . ? C7' H7'C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 123.48(17) . . ? C1 N1 H1N 118.3 . . ? C2 N1 H1N 118.3 . . ? C1' N2' C4' 122.72(16) . . ? C1' N2' H2N' 118.6 . . ? C4' N2' H2N' 118.6 . . ? C1' N1' C2' 122.56(17) . . ? C1' N1' H1N' 118.7 . . ? C2' N1' H1N' 118.7 . . ? C2 C3 C5 121.69(18) . . ? C2 C3 C4 118.78(19) . . ? C5 C3 C4 119.46(17) . . ? C1 N2 C4 121.60(16) . . ? C1 N2 H2N 119.2 . . ? C4 N2 H2N 119.2 . . ? C5 O3 C6 115.50(17) . . ? O1 C1 N2 124.02(18) . . ? O1 C1 N1 120.67(17) . . ? N2 C1 N1 115.30(19) . . ? C12' O4' C15' 117.20(18) . . ? C2' C3' C5' 121.68(19) . . ? C2' C3' C4' 118.62(19) . . ? C5' C3' C4' 119.66(18) . . ? C5' O3' C6' 116.88(18) . . ? C12 O4 C15 117.17(19) . . ? O1' C1' N2' 123.39(18) . . ? O1' C1' N1' 120.40(18) . . ? N2' C1' N1' 116.22(19) . . ? C14' C9' C10' 117.7(2) . . ? C14' C9' C4' 122.76(19) . . ? C10' C9' C4' 119.46(19) . . ? O2 C5 O3 122.3(2) . . ? O2 C5 C3 126.88(19) . . ? O3 C5 C3 110.73(18) . . ? C3 C2 N1 118.73(18) . . ? C3 C2 C8 128.1(2) . . ? N1 C2 C8 113.20(17) . . ? C3' C2' N1' 118.45(18) . . ? C3' C2' C8' 128.0(2) . . ? N1' C2' C8' 113.53(18) . . ? C9' C14' C13' 122.0(2) . . ? C9' C14' H14' 119.0 . . ? C13' C14' H14' 119.0 . . ? O2' C5' O3' 122.6(2) . . ? O2' C5' C3' 126.3(2) . . ? O3' C5' C3' 111.10(19) . . ? N2 C4 C3 108.45(15) . . ? N2 C4 C9 109.90(17) . . ? C3 C4 C9 114.77(16) . . ? N2 C4 H4 107.8 . . ? C3 C4 H4 107.8 . . ? C9 C4 H4 107.8 . . ? C11 C12 O4 125.1(2) . . ? C11 C12 C13 119.2(2) . . ? O4 C12 C13 115.7(2) . . ? O4' C12' C13' 124.8(2) . . ? O4' C12' C11' 116.0(2) . . ? C13' C12' C11' 119.2(2) . . ? C11' C10' C9' 120.9(2) . . ? C11' C10' H10' 119.5 . . ? C9' C10' H10' 119.5 . . ? C12' C13' C14' 119.4(2) . . ? C12' C13' H13' 120.3 . . ? C14' C13' H13' 120.3 . . ? N2' C4' C3' 108.63(16) . . ? N2' C4' C9' 112.38(17) . . ? C3' C4' C9' 111.06(16) . . ? N2' C4' H4' 108.2 . . ? C3' C4' H4' 108.2 . . ? C9' C4' H4' 108.2 . . ? C13 C14 C9 121.9(2) . . ? C13 C14 H14 119.1 . . ? C9 C14 H14 119.1 . . ? C10' C11' C12' 120.8(2) . . ? C10' C11' H11' 119.6 . . ? C12' C11' H11' 119.6 . . ? C10 C9 C14 117.15(19) . . ? C10 C9 C4 123.18(19) . . ? C14 C9 C4 119.67(18) . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C13 C12 119.9(2) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C9 C10 C11 121.9(2) . . ? C9 C10 H10 119.1 . . ? C11 C10 H10 119.1 . . ? C12 C11 C10 120.0(2) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C2' C8' H8'A 109.5 . . ? C2' C8' H8'B 109.5 . . ? H8'A C8' H8'B 109.5 . . ? C2' C8' H8'C 109.5 . . ? H8'A C8' H8'C 109.5 . . ? H8'B C8' H8'C 109.5 . . ? O4' C15' H15D 109.5 . . ? O4' C15' H15E 109.5 . . ? H15D C15' H15E 109.5 . . ? O4' C15' H15F 109.5 . . ? H15D C15' H15F 109.5 . . ? H15E C15' H15F 109.5 . . ? O3 C6 C7 108.4(2) . . ? O3 C6 H6A 110.0 . . ? C7 C6 H6A 110.0 . . ? O3 C6 H6B 110.0 . . ? C7 C6 H6B 110.0 . . ? H6A C6 H6B 108.4 . . ? C7' C6' O3' 110.3(2) . . ? C7' C6' H6'A 109.6 . . ? O3' C6' H6'A 109.6 . . ? C7' C6' H6'B 109.6 . . ? O3' C6' H6'B 109.6 . . ? H6'A C6' H6'B 108.1 . . ? O4 C15 H15A 109.5 . . ? O4 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O4 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6' C7' H7'A 109.5 . . ? C6' C7' H7'B 109.5 . . ? H7'A C7' H7'B 109.5 . . ? C6' C7' H7'C 109.5 . . ? H7'A C7' H7'C 109.5 . . ? H7'B C7' H7'C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N2 C1 O1 -157.32(18) . . . . ? C4 N2 C1 N1 24.4(3) . . . . ? C2 N1 C1 O1 -169.85(17) . . . . ? C2 N1 C1 N2 8.5(3) . . . . ? C4' N2' C1' O1' -164.81(18) . . . . ? C4' N2' C1' N1' 15.5(3) . . . . ? C2' N1' C1' O1' -164.80(18) . . . . ? C2' N1' C1' N2' 14.9(3) . . . . ? C6 O3 C5 O2 -0.6(3) . . . . ? C6 O3 C5 C3 -178.51(18) . . . . ? C2 C3 C5 O2 3.4(3) . . . . ? C4 C3 C5 O2 -173.6(2) . . . . ? C2 C3 C5 O3 -178.81(17) . . . . ? C4 C3 C5 O3 4.2(3) . . . . ? C5 C3 C2 N1 -179.82(17) . . . . ? C4 C3 C2 N1 -2.8(3) . . . . ? C5 C3 C2 C8 0.3(3) . . . . ? C4 C3 C2 C8 177.27(18) . . . . ? C1 N1 C2 C3 -19.1(3) . . . . ? C1 N1 C2 C8 160.79(17) . . . . ? C5' C3' C2' N1' 173.44(18) . . . . ? C4' C3' C2' N1' -8.6(3) . . . . ? C5' C3' C2' C8' -4.9(3) . . . . ? C4' C3' C2' C8' 173.00(19) . . . . ? C1' N1' C2' C3' -17.9(3) . . . . ? C1' N1' C2' C8' 160.68(17) . . . . ? C10' C9' C14' C13' 1.0(3) . . . . ? C4' C9' C14' C13' -174.94(19) . . . . ? C6' O3' C5' O2' -0.5(3) . . . . ? C6' O3' C5' C3' 179.71(19) . . . . ? C2' C3' C5' O2' 7.8(3) . . . . ? C4' C3' C5' O2' -170.1(2) . . . . ? C2' C3' C5' O3' -172.38(18) . . . . ? C4' C3' C5' O3' 9.7(3) . . . . ? C1 N2 C4 C3 -42.1(2) . . . . ? C1 N2 C4 C9 84.1(2) . . . . ? C2 C3 C4 N2 29.7(2) . . . . ? C5 C3 C4 N2 -153.19(17) . . . . ? C2 C3 C4 C9 -93.6(2) . . . . ? C5 C3 C4 C9 83.5(2) . . . . ? C15 O4 C12 C11 3.3(3) . . . . ? C15 O4 C12 C13 -177.5(2) . . . . ? C15' O4' C12' C13' -6.7(3) . . . . ? C15' O4' C12' C11' 173.46(19) . . . . ? C14' C9' C10' C11' -0.3(3) . . . . ? C4' C9' C10' C11' 175.70(19) . . . . ? O4' C12' C13' C14' 178.68(19) . . . . ? C11' C12' C13' C14' -1.4(3) . . . . ? C9' C14' C13' C12' -0.1(3) . . . . ? C1' N2' C4' C3' -37.8(2) . . . . ? C1' N2' C4' C9' 85.5(2) . . . . ? C2' C3' C4' N2' 33.2(2) . . . . ? C5' C3' C4' N2' -148.79(18) . . . . ? C2' C3' C4' C9' -90.9(2) . . . . ? C5' C3' C4' C9' 87.1(2) . . . . ? C14' C9' C4' N2' -33.2(3) . . . . ? C10' C9' C4' N2' 150.92(19) . . . . ? C14' C9' C4' C3' 88.7(2) . . . . ? C10' C9' C4' C3' -87.1(2) . . . . ? C9' C10' C11' C12' -1.2(3) . . . . ? O4' C12' C11' C10' -178.04(19) . . . . ? C13' C12' C11' C10' 2.1(3) . . . . ? C13 C14 C9 C10 1.8(3) . . . . ? C13 C14 C9 C4 -178.2(2) . . . . ? N2 C4 C9 C10 -132.2(2) . . . . ? C3 C4 C9 C10 -9.7(3) . . . . ? N2 C4 C9 C14 47.8(2) . . . . ? C3 C4 C9 C14 170.35(19) . . . . ? C9 C14 C13 C12 -1.1(4) . . . . ? C11 C12 C13 C14 0.0(4) . . . . ? O4 C12 C13 C14 -179.4(2) . . . . ? C14 C9 C10 C11 -1.5(3) . . . . ? C4 C9 C10 C11 178.6(2) . . . . ? O4 C12 C11 C10 179.6(2) . . . . ? C13 C12 C11 C10 0.4(4) . . . . ? C9 C10 C11 C12 0.4(4) . . . . ? C5 O3 C6 C7 164.4(2) . . . . ? C5' O3' C6' C7' -84.9(3) . . . . ? #===END # Attachment '- PYOX7.cif' # CIF-file generated for 03OC in P2(1)/n #============================================================================== data_03oc _database_code_depnum_ccdc_archive 'CCDC 761385' #TrackingRef '- PYOX7.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H18 N2 O4' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C15 H18 N2 O4' _chemical_formula_iupac ? _chemical_formula_weight 290.31 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z _cell_length_a 12.2450(4) _cell_length_b 7.4478(2) _cell_length_c 16.1914(5) _cell_angle_alpha 90 _cell_angle_beta 106.676(3) _cell_angle_gamma 90 _cell_volume 1414.53(8) _cell_formula_units_Z 4 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 430 _cell_measurement_theta_min 0.97 _cell_measurement_theta_max 27.89 _cell_special_details ; ; _exptl_crystal_description Prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.100 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.9793 _exptl_absorpt_correction_T_max 0.9901 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Goniometer Xcalibur, detector: Eos (Nova)' _diffrn_detector_area_resol_mean 16.0839 _diffrn_orient_matrix_UB_11 0.0023299711 _diffrn_orient_matrix_UB_12 0.0278710396 _diffrn_orient_matrix_UB_13 -0.0413168949 _diffrn_orient_matrix_UB_21 -0.0092871757 _diffrn_orient_matrix_UB_22 0.0900914661 _diffrn_orient_matrix_UB_23 0.0104121522 _diffrn_orient_matrix_UB_31 0.0596569560 _diffrn_orient_matrix_UB_32 0.0129083379 _diffrn_orient_matrix_UB_33 0.0165227003 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -8.00 21.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - -17.1989 -95.0000 110.0000 29 #__ type_ start__ end____ width___ exp.time_ 2 omega -68.00 -39.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - -17.1989 179.0000 -60.0000 29 #__ type_ start__ end____ width___ exp.time_ 3 omega -51.00 47.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 -77.0000 0.0000 98 #__ type_ start__ end____ width___ exp.time_ 4 omega -11.00 81.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 77.0000 120.0000 92 #__ type_ start__ end____ width___ exp.time_ 5 omega -90.00 9.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - -17.1989 -37.0000 -180.0000 99 #__ type_ start__ end____ width___ exp.time_ 6 omega -7.00 92.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 37.0000 0.0000 99 #__ type_ start__ end____ width___ exp.time_ 7 omega -7.00 36.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 37.0000 90.0000 43 #__ type_ start__ end____ width___ exp.time_ 8 omega -4.00 72.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 19.0739 -118.0000 -115.0000 76 ; _diffrn_measurement_method '\w scans' # number of measured reflections (redundant set) _diffrn_reflns_number 14691 _diffrn_reflns_av_R_equivalents 0.0463 _diffrn_reflns_av_sigmaI/netI 0.0459 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 26.00 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 2774 # number of observed reflections (> n sig(I)) _reflns_number_gt 1807 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (2009) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0604P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2774 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0770 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.1133 _refine_ls_wR_factor_gt 0.1069 _refine_ls_goodness_of_fit_ref 0.968 _refine_ls_restrained_S_all 0.968 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.201 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.043 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT 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 1.27290(10) 0.53202(15) 0.75863(8) 0.0394(4) Uani 1 1 d . . . N2 N 1.11400(11) 0.68743(18) 0.68992(9) 0.0311(4) Uani 1 1 d . . . H2N H 1.1515 0.7864 0.6944 0.037 Uiso 1 1 calc R . . O3 O 0.80399(10) 0.70753(16) 0.51723(8) 0.0412(4) Uani 1 1 d . . . N1 N 1.11216(12) 0.38070(19) 0.68664(9) 0.0344(4) Uani 1 1 d . . . H1N H 1.1393 0.2813 0.7110 0.041 Uiso 1 1 calc R . . O2 O 0.79560(11) 0.41478(18) 0.48542(8) 0.0456(4) Uani 1 1 d . . . C5 C 0.84381(14) 0.5383(2) 0.52874(11) 0.0312(4) Uani 1 1 d . . . C2 C 1.01020(14) 0.3766(2) 0.62058(11) 0.0293(4) Uani 1 1 d . . . C3 C 0.95024(14) 0.5292(2) 0.59999(11) 0.0275(4) Uani 1 1 d . . . O4 O 0.92716(13) 1.03835(19) 0.89863(9) 0.0567(4) Uani 1 1 d . . . C9 C 0.93421(14) 0.7142(2) 0.72791(11) 0.0284(4) Uani 1 1 d . . . C4 C 0.98912(14) 0.6933(2) 0.65509(11) 0.0282(4) Uani 1 1 d . . . H4 H 0.9692 0.7992 0.6178 0.034 Uiso 1 1 calc R . . C1 C 1.17139(14) 0.5363(2) 0.71465(11) 0.0294(4) Uani 1 1 d . . . C14 C 0.95729(15) 0.8693(2) 0.77835(12) 0.0341(4) Uani 1 1 d . . . H14 H 1.0036 0.9583 0.7661 0.041 Uiso 1 1 calc R . . C6 C 0.69621(15) 0.7317(3) 0.45097(12) 0.0431(5) Uani 1 1 d . . . H6A H 0.6365 0.6650 0.4658 0.052 Uiso 1 1 calc R . . H6B H 0.7022 0.6877 0.3960 0.052 Uiso 1 1 calc R . . C10 C 0.86469(15) 0.5843(3) 0.74673(12) 0.0380(5) Uani 1 1 d . . . H10 H 0.8479 0.4811 0.7131 0.046 Uiso 1 1 calc R . . C12 C 0.84271(16) 0.7576(3) 0.86543(12) 0.0437(5) Uani 1 1 d . . . H12 H 0.8127 0.7711 0.9117 0.052 Uiso 1 1 calc R . . C8 C 0.98113(16) 0.1956(2) 0.58062(13) 0.0416(5) Uani 1 1 d . . . H8A H 0.9476 0.2086 0.5196 0.062 Uiso 1 1 calc R . . H8B H 0.9279 0.1374 0.6053 0.062 Uiso 1 1 calc R . . H8C H 1.0492 0.1245 0.5913 0.062 Uiso 1 1 calc R . . C13 C 0.91134(15) 0.8908(2) 0.84658(12) 0.0366(5) Uani 1 1 d . . . C11 C 0.81977(16) 0.6069(3) 0.81553(13) 0.0442(5) Uani 1 1 d . . . H11 H 0.7734 0.5181 0.8278 0.053 Uiso 1 1 calc R . . C7 C 0.6688(2) 0.9258(3) 0.44484(15) 0.0639(7) Uani 1 1 d . . . H7A H 0.7285 0.9907 0.4304 0.096 Uiso 1 1 calc R . . H7B H 0.6618 0.9677 0.4992 0.096 Uiso 1 1 calc R . . H7C H 0.5981 0.9450 0.4009 0.096 Uiso 1 1 calc R . . C15 C 0.9955(2) 1.1801(3) 0.88247(16) 0.0657(7) Uani 1 1 d . . . H15A H 0.9622 1.2262 0.8254 0.098 Uiso 1 1 calc R . . H15B H 1.0707 1.1359 0.8872 0.098 Uiso 1 1 calc R . . H15C H 0.9999 1.2742 0.9238 0.098 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0261(7) 0.0327(7) 0.0512(8) -0.0016(6) -0.0021(6) 0.0014(6) N2 0.0245(8) 0.0236(8) 0.0426(9) -0.0003(7) 0.0056(7) -0.0027(7) O3 0.0360(7) 0.0360(8) 0.0410(8) 0.0005(6) -0.0062(6) 0.0032(6) N1 0.0336(9) 0.0227(8) 0.0403(9) 0.0039(7) 0.0001(7) 0.0013(7) O2 0.0402(8) 0.0429(8) 0.0447(8) -0.0114(7) -0.0022(6) -0.0036(6) C5 0.0293(10) 0.0348(11) 0.0292(9) -0.0013(9) 0.0079(8) -0.0022(9) C2 0.0285(10) 0.0287(10) 0.0298(10) -0.0002(8) 0.0070(8) -0.0027(8) C3 0.0273(9) 0.0259(9) 0.0283(9) -0.0005(8) 0.0065(8) -0.0017(8) O4 0.0739(10) 0.0469(9) 0.0518(9) -0.0192(7) 0.0217(8) -0.0026(8) C9 0.0244(9) 0.0267(10) 0.0302(9) -0.0003(8) 0.0016(8) 0.0027(8) C4 0.0261(9) 0.0235(9) 0.0312(10) 0.0005(8) 0.0024(8) 0.0001(7) C1 0.0283(10) 0.0269(10) 0.0321(10) -0.0016(8) 0.0072(8) 0.0003(8) C14 0.0327(10) 0.0292(10) 0.0377(11) -0.0007(9) 0.0057(8) 0.0012(8) C6 0.0322(11) 0.0524(13) 0.0363(11) -0.0006(10) -0.0039(9) 0.0070(9) C10 0.0359(10) 0.0378(11) 0.0402(11) -0.0073(9) 0.0106(9) -0.0058(9) C12 0.0411(12) 0.0551(13) 0.0366(11) -0.0006(10) 0.0140(9) 0.0060(10) C8 0.0431(11) 0.0296(11) 0.0485(12) -0.0072(9) 0.0072(10) -0.0033(9) C13 0.0375(11) 0.0333(11) 0.0343(10) -0.0054(9) 0.0030(9) 0.0056(9) C11 0.0376(11) 0.0496(13) 0.0478(12) -0.0009(11) 0.0161(10) -0.0088(10) C7 0.0608(14) 0.0561(15) 0.0597(15) 0.0010(12) -0.0066(12) 0.0198(12) C15 0.0896(19) 0.0374(13) 0.0694(16) -0.0172(12) 0.0218(14) -0.0078(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2431(19) . ? N2 C1 1.326(2) . ? N2 C4 1.471(2) . ? N2 H2N 0.8600 . ? O3 C5 1.345(2) . ? O3 C6 1.4535(19) . ? N1 C1 1.374(2) . ? N1 C2 1.392(2) . ? N1 H1N 0.8600 . ? O2 C5 1.204(2) . ? C5 C3 1.473(2) . ? C2 C3 1.342(2) . ? C2 C8 1.494(2) . ? C3 C4 1.508(2) . ? O4 C13 1.364(2) . ? O4 C15 1.418(3) . ? C9 C10 1.379(2) . ? C9 C14 1.396(2) . ? C9 C4 1.524(2) . ? C4 H4 0.9800 . ? C14 C13 1.386(3) . ? C14 H14 0.9300 . ? C6 C7 1.482(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C10 C11 1.387(3) . ? C10 H10 0.9300 . ? C12 C11 1.364(3) . ? C12 C13 1.389(3) . ? C12 H12 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C11 H11 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N2 C4 122.93(13) . . ? C1 N2 H2N 118.5 . . ? C4 N2 H2N 118.5 . . ? C5 O3 C6 115.74(14) . . ? C1 N1 C2 122.98(14) . . ? C1 N1 H1N 118.5 . . ? C2 N1 H1N 118.5 . . ? O2 C5 O3 122.53(16) . . ? O2 C5 C3 126.65(16) . . ? O3 C5 C3 110.82(15) . . ? C3 C2 N1 118.60(15) . . ? C3 C2 C8 127.69(16) . . ? N1 C2 C8 113.72(15) . . ? C2 C3 C5 122.09(15) . . ? C2 C3 C4 118.83(15) . . ? C5 C3 C4 118.97(14) . . ? C13 O4 C15 118.20(17) . . ? C10 C9 C14 119.04(17) . . ? C10 C9 C4 122.47(15) . . ? C14 C9 C4 118.47(15) . . ? N2 C4 C3 108.64(13) . . ? N2 C4 C9 110.33(13) . . ? C3 C4 C9 113.95(14) . . ? N2 C4 H4 107.9 . . ? C3 C4 H4 107.9 . . ? C9 C4 H4 107.9 . . ? O1 C1 N2 123.44(15) . . ? O1 C1 N1 120.91(15) . . ? N2 C1 N1 115.63(14) . . ? C13 C14 C9 120.12(17) . . ? C13 C14 H14 119.9 . . ? C9 C14 H14 119.9 . . ? O3 C6 C7 108.09(15) . . ? O3 C6 H6A 110.1 . . ? C7 C6 H6A 110.1 . . ? O3 C6 H6B 110.1 . . ? C7 C6 H6B 110.1 . . ? H6A C6 H6B 108.4 . . ? C9 C10 C11 120.29(18) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C11 C12 C13 119.49(19) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O4 C13 C14 124.58(18) . . ? O4 C13 C12 115.28(18) . . ? C14 C13 C12 120.13(17) . . ? C12 C11 C10 120.91(19) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O4 C15 H15A 109.5 . . ? O4 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O4 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 O3 C5 O2 2.2(3) . . . . ? C6 O3 C5 C3 -177.33(14) . . . . ? C1 N1 C2 C3 -19.6(3) . . . . ? C1 N1 C2 C8 160.40(16) . . . . ? N1 C2 C3 C5 177.57(15) . . . . ? C8 C2 C3 C5 -2.4(3) . . . . ? N1 C2 C3 C4 -6.4(3) . . . . ? C8 C2 C3 C4 173.59(17) . . . . ? O2 C5 C3 C2 4.6(3) . . . . ? O3 C5 C3 C2 -175.88(16) . . . . ? O2 C5 C3 C4 -171.42(17) . . . . ? O3 C5 C3 C4 8.1(2) . . . . ? C1 N2 C4 C3 -37.3(2) . . . . ? C1 N2 C4 C9 88.33(19) . . . . ? C2 C3 C4 N2 31.3(2) . . . . ? C5 C3 C4 N2 -152.51(15) . . . . ? C2 C3 C4 C9 -92.12(19) . . . . ? C5 C3 C4 C9 84.05(19) . . . . ? C10 C9 C4 N2 -116.05(16) . . . . ? C14 C9 C4 N2 62.64(18) . . . . ? C10 C9 C4 C3 6.5(2) . . . . ? C14 C9 C4 C3 -174.84(15) . . . . ? C4 N2 C1 O1 -165.98(16) . . . . ? C4 N2 C1 N1 15.6(2) . . . . ? C2 N1 C1 O1 -163.21(16) . . . . ? C2 N1 C1 N2 15.2(2) . . . . ? C10 C9 C14 C13 0.4(2) . . . . ? C4 C9 C14 C13 -178.29(15) . . . . ? C5 O3 C6 C7 -177.47(17) . . . . ? C14 C9 C10 C11 -0.8(2) . . . . ? C4 C9 C10 C11 177.84(16) . . . . ? C15 O4 C13 C14 -0.2(3) . . . . ? C15 O4 C13 C12 -179.46(17) . . . . ? C9 C14 C13 O4 -178.83(16) . . . . ? C9 C14 C13 C12 0.4(3) . . . . ? C11 C12 C13 O4 178.42(17) . . . . ? C11 C12 C13 C14 -0.9(3) . . . . ? C13 C12 C11 C10 0.5(3) . . . . ? C9 C10 C11 C12 0.4(3) . . . . ? #===END # Attachment '- PYOX8.cif' # CIF-file generated for O4O3OC in P2(1)/n #============================================================================== data_o4o3oc _database_code_depnum_ccdc_archive 'CCDC 761386' #TrackingRef '- PYOX8.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H18 N2 O5' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C15 H18 N2 O5' _chemical_formula_iupac ? _chemical_formula_weight 306.31 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z _cell_length_a 12.2806(10) _cell_length_b 7.4567(6) _cell_length_c 17.2659(14) _cell_angle_alpha 90 _cell_angle_beta 109.584(9) _cell_angle_gamma 90 _cell_volume 1489.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 430 _cell_measurement_theta_min 0.97 _cell_measurement_theta_max 27.98 _cell_special_details ; ; _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.366 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.103 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.9596 _exptl_absorpt_correction_T_max 0.9816 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Goniometer Xcalibur, detector: Eos (Nova)' _diffrn_detector_area_resol_mean 16.0839 _diffrn_orient_matrix_UB_11 -0.0521183343 _diffrn_orient_matrix_UB_12 -0.0174247475 _diffrn_orient_matrix_UB_13 0.0078915189 _diffrn_orient_matrix_UB_21 -0.0299360879 _diffrn_orient_matrix_UB_22 -0.0083441756 _diffrn_orient_matrix_UB_23 -0.0428346693 _diffrn_orient_matrix_UB_31 0.0124487087 _diffrn_orient_matrix_UB_32 -0.0933108870 _diffrn_orient_matrix_UB_33 0.0023387983 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -17.00 12.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.0427 -77.0000 0.0000 29 #__ type_ start__ end____ width___ exp.time_ 2 omega -87.00 -58.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.0427 179.0000 150.0000 29 #__ type_ start__ end____ width___ exp.time_ 3 omega -7.00 91.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 18.9177 37.0000 150.0000 98 #__ type_ start__ end____ width___ exp.time_ 4 omega 3.00 91.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 18.9177 37.0000 60.0000 88 #__ type_ start__ end____ width___ exp.time_ 5 omega -87.00 13.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.0427 -77.0000 -90.0000 100 #__ type_ start__ end____ width___ exp.time_ 6 omega -94.00 -34.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.0427 179.0000 60.0000 60 #__ type_ start__ end____ width___ exp.time_ 7 omega -94.00 -34.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.0427 179.0000 -180.0000 60 #__ type_ start__ end____ width___ exp.time_ 8 omega -47.00 53.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.0427 77.0000 30.0000 100 ; _diffrn_measurement_method '\w scans' _diffrn_reflns_number 15352 _diffrn_reflns_av_R_equivalents 0.0424 _diffrn_reflns_av_sigmaI/netI 0.0351 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 26.00 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 2923 # number of observed reflections (> n sig(I)) _reflns_number_gt 1887 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (2009) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0796P)^2^+0.1929P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2923 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0838 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1563 _refine_ls_wR_factor_gt 0.1437 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.441 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.041 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT 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 -0.27501(12) 0.0472(2) 0.24550(10) 0.0476(4) Uani 1 1 d . . . O4 O 0.1964(2) 0.2316(3) 0.08762(13) 0.0813(7) Uani 1 1 d . . . H4O H 0.1820 0.3287 0.0641 0.122 Uiso 1 1 calc R . . N2 N -0.11452(14) 0.2065(2) 0.31420(11) 0.0387(5) Uani 1 1 d . . . H2N H -0.1525 0.3051 0.3094 0.046 Uiso 1 1 calc R . . O5 O 0.07201(18) 0.5098(3) 0.10856(11) 0.0746(6) Uani 1 1 d . A . O2 O 0.21556(16) -0.0541(3) 0.51635(11) 0.0714(6) Uani 1 1 d . . . O3 O 0.19839(15) 0.2348(2) 0.48684(12) 0.0709(6) Uani 1 1 d . . . N1 N -0.11159(14) -0.1003(2) 0.32084(11) 0.0409(5) Uani 1 1 d . . . H1N H -0.1393 -0.2010 0.2986 0.049 Uiso 1 1 calc R . . C1 C -0.17235(17) 0.0537(3) 0.29040(13) 0.0365(5) Uani 1 1 d . . . C4 C 0.01223(17) 0.2115(3) 0.34832(13) 0.0364(5) Uani 1 1 d . A . H4 H 0.0351 0.3213 0.3810 0.044 Uiso 1 1 calc R . . C3 C 0.05288(17) 0.0523(3) 0.40528(12) 0.0363(5) Uani 1 1 d . . . C10 C 0.12938(19) 0.0770(3) 0.26576(14) 0.0451(6) Uani 1 1 d . A . H10 H 0.1442 -0.0230 0.3000 0.054 Uiso 1 1 calc R . . C14 C 0.04319(19) 0.3658(3) 0.22780(14) 0.0460(6) Uani 1 1 d . A . H14 H -0.0003 0.4610 0.2364 0.055 Uiso 1 1 calc R . . C9 C 0.06459(17) 0.2165(3) 0.27968(13) 0.0367(5) Uani 1 1 d . . . C2 C -0.00691(18) -0.1011(3) 0.38630(13) 0.0366(5) Uani 1 1 d . A . C8 C 0.0245(2) -0.2804(3) 0.42713(16) 0.0503(6) Uani 1 1 d . . . H8A H 0.0758 -0.3416 0.4045 0.076 Uiso 1 1 calc R A . H8B H -0.0443 -0.3504 0.4178 0.076 Uiso 1 1 calc R . . H8C H 0.0621 -0.2638 0.4851 0.076 Uiso 1 1 calc R . . C13 C 0.0869(2) 0.3716(3) 0.16345(14) 0.0511(6) Uani 1 1 d . . . C11 C 0.1727(2) 0.0842(4) 0.20113(15) 0.0520(6) Uani 1 1 d . . . H11 H 0.2163 -0.0108 0.1925 0.062 Uiso 1 1 calc R A . C12 C 0.1520(2) 0.2282(4) 0.15068(15) 0.0528(7) Uani 1 1 d . A . C5 C 0.1621(2) 0.0671(3) 0.47452(14) 0.0449(6) Uani 1 1 d . A . C6A C 0.3045(4) 0.2572(6) 0.5585(5) 0.0579(16) Uani 0.762(17) 1 d P A 1 H6A1 H 0.2963 0.1970 0.6060 0.069 Uiso 0.762(17) 1 calc PR A 1 H6A2 H 0.3700 0.2058 0.5471 0.069 Uiso 0.762(17) 1 calc PR A 1 C6B C 0.3279(15) 0.308(3) 0.5193(15) 0.070(7) Uani 0.238(17) 1 d P A 2 H6B1 H 0.3817 0.2144 0.5475 0.084 Uiso 0.238(17) 1 calc PR A 2 H6B2 H 0.3507 0.3545 0.4746 0.084 Uiso 0.238(17) 1 calc PR A 2 C15 C 0.0114(3) 0.6641(4) 0.1208(2) 0.0886(11) Uani 1 1 d . . . H15A H -0.0651 0.6303 0.1183 0.133 Uiso 1 1 calc R A . H15B H 0.0067 0.7508 0.0787 0.133 Uiso 1 1 calc R . . H15C H 0.0518 0.7153 0.1737 0.133 Uiso 1 1 calc R . . C7 C 0.3219(3) 0.4458(5) 0.5742(2) 0.0998(12) Uani 1 1 d . . . H7A H 0.3904 0.4644 0.6208 0.150 Uiso 1 1 calc R A 1 H7B H 0.2565 0.4953 0.5854 0.150 Uiso 1 1 calc R A 1 H7C H 0.3303 0.5039 0.5269 0.150 Uiso 1 1 calc R A 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0277(8) 0.0400(9) 0.0626(10) -0.0004(7) -0.0014(7) -0.0008(7) O4 0.0879(16) 0.1021(17) 0.0628(13) 0.0054(11) 0.0371(13) -0.0142(13) N2 0.0274(9) 0.0311(10) 0.0507(11) -0.0028(8) 0.0039(8) 0.0022(7) O5 0.0895(15) 0.0624(13) 0.0619(12) 0.0239(10) 0.0121(11) -0.0098(11) O2 0.0603(12) 0.0742(14) 0.0553(11) 0.0048(10) -0.0128(9) 0.0173(10) O3 0.0469(11) 0.0579(12) 0.0768(13) -0.0106(9) -0.0206(9) -0.0029(9) N1 0.0343(10) 0.0309(10) 0.0481(11) -0.0020(8) 0.0015(9) -0.0004(8) C1 0.0302(12) 0.0362(12) 0.0395(12) 0.0001(9) 0.0067(9) 0.0017(9) C4 0.0256(11) 0.0319(11) 0.0424(12) -0.0054(9) -0.0010(9) 0.0008(9) C3 0.0310(11) 0.0414(13) 0.0325(11) -0.0010(9) 0.0055(9) 0.0054(10) C10 0.0374(12) 0.0492(14) 0.0450(13) 0.0078(11) 0.0088(10) 0.0042(11) C14 0.0384(13) 0.0396(13) 0.0499(14) 0.0015(11) 0.0014(11) -0.0055(10) C9 0.0271(11) 0.0360(12) 0.0377(12) 0.0001(9) -0.0016(9) -0.0045(9) C2 0.0345(12) 0.0389(12) 0.0345(11) 0.0010(9) 0.0093(9) 0.0065(9) C8 0.0478(14) 0.0429(14) 0.0554(15) 0.0080(11) 0.0108(12) 0.0076(11) C13 0.0490(14) 0.0481(15) 0.0431(14) 0.0097(11) -0.0018(11) -0.0165(12) C11 0.0412(14) 0.0613(16) 0.0513(15) 0.0006(12) 0.0128(12) 0.0058(12) C12 0.0431(14) 0.0683(18) 0.0447(14) 0.0000(13) 0.0117(12) -0.0139(13) C5 0.0392(13) 0.0512(15) 0.0370(12) -0.0088(11) 0.0028(10) 0.0093(12) C6A 0.035(2) 0.070(3) 0.049(3) 0.007(2) -0.0121(18) -0.0143(17) C6B 0.052(9) 0.082(12) 0.053(10) -0.001(9) -0.014(7) 0.013(7) C15 0.114(3) 0.0551(19) 0.075(2) 0.0250(16) 0.004(2) -0.0074(18) C7 0.084(2) 0.099(3) 0.080(2) -0.010(2) -0.0201(19) -0.022(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.240(2) . ? O4 C12 1.371(3) . ? O4 H4O 0.8200 . ? N2 C1 1.333(3) . ? N2 C4 1.469(2) . ? N2 H2N 0.8600 . ? O5 C13 1.370(3) . ? O5 C15 1.425(4) . ? O2 C5 1.205(3) . ? O3 C5 1.321(3) . ? O3 C6A 1.475(4) . ? O3 C6B 1.59(2) . ? N1 C1 1.374(3) . ? N1 C2 1.399(3) . ? N1 H1N 0.8600 . ? C4 C3 1.515(3) . ? C4 C9 1.527(3) . ? C4 H4 0.9800 . ? C3 C2 1.339(3) . ? C3 C5 1.472(3) . ? C10 C9 1.379(3) . ? C10 C11 1.389(3) . ? C10 H10 0.9300 . ? C14 C13 1.387(3) . ? C14 C9 1.397(3) . ? C14 H14 0.9300 . ? C2 C8 1.500(3) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C13 C12 1.396(4) . ? C11 C12 1.352(3) . ? C11 H11 0.9300 . ? C6A C7 1.435(5) . ? C6A H6A1 0.9700 . ? C6A H6A2 0.9700 . ? C6B C7 1.420(16) . ? C6B H6B1 0.9700 . ? C6B H6B2 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 O4 H4O 109.5 . . ? C1 N2 C4 121.95(17) . . ? C1 N2 H2N 119.0 . . ? C4 N2 H2N 119.0 . . ? C13 O5 C15 117.4(2) . . ? C5 O3 C6A 113.5(3) . . ? C5 O3 C6B 128.5(7) . . ? C1 N1 C2 123.15(18) . . ? C1 N1 H1N 118.4 . . ? C2 N1 H1N 118.4 . . ? O1 C1 N2 123.45(19) . . ? O1 C1 N1 120.97(19) . . ? N2 C1 N1 115.56(18) . . ? N2 C4 C3 108.34(17) . . ? N2 C4 C9 110.79(16) . . ? C3 C4 C9 112.97(17) . . ? N2 C4 H4 108.2 . . ? C3 C4 H4 108.2 . . ? C9 C4 H4 108.2 . . ? C2 C3 C5 122.6(2) . . ? C2 C3 C4 118.42(18) . . ? C5 C3 C4 118.75(19) . . ? C9 C10 C11 120.6(2) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C13 C14 C9 119.9(2) . . ? C13 C14 H14 120.1 . . ? C9 C14 H14 120.1 . . ? C10 C9 C14 119.0(2) . . ? C10 C9 C4 122.32(19) . . ? C14 C9 C4 118.7(2) . . ? C3 C2 N1 118.31(19) . . ? C3 C2 C8 127.8(2) . . ? N1 C2 C8 113.91(19) . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O5 C13 C14 125.4(2) . . ? O5 C13 C12 114.7(2) . . ? C14 C13 C12 119.9(2) . . ? C12 C11 C10 120.6(2) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 O4 119.2(3) . . ? C11 C12 C13 120.0(2) . . ? O4 C12 C13 120.8(2) . . ? O2 C5 O3 121.8(2) . . ? O2 C5 C3 126.6(2) . . ? O3 C5 C3 111.59(19) . . ? C7 C6A O3 107.7(3) . . ? C7 C6A H6A1 110.2 . . ? O3 C6A H6A1 110.2 . . ? C7 C6A H6A2 110.2 . . ? O3 C6A H6A2 110.2 . . ? H6A1 C6A H6A2 108.5 . . ? C7 C6B O3 102.3(14) . . ? C7 C6B H6B1 111.3 . . ? O3 C6B H6B1 111.3 . . ? C7 C6B H6B2 111.3 . . ? O3 C6B H6B2 111.3 . . ? H6B1 C6B H6B2 109.2 . . ? O5 C15 H15A 109.5 . . ? O5 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O5 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C6B C7 H7A 115.9 . . ? C6A C7 H7A 109.5 . . ? C6B C7 H7B 130.4 . . ? C6A C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6A C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N2 C1 O1 -163.5(2) . . . . ? C4 N2 C1 N1 18.2(3) . . . . ? C2 N1 C1 O1 -164.04(19) . . . . ? C2 N1 C1 N2 14.2(3) . . . . ? C1 N2 C4 C3 -40.7(3) . . . . ? C1 N2 C4 C9 83.7(2) . . . . ? N2 C4 C3 C2 34.3(3) . . . . ? C9 C4 C3 C2 -88.9(2) . . . . ? N2 C4 C3 C5 -151.52(18) . . . . ? C9 C4 C3 C5 85.3(2) . . . . ? C11 C10 C9 C14 -0.1(3) . . . . ? C11 C10 C9 C4 178.1(2) . . . . ? C13 C14 C9 C10 0.1(3) . . . . ? C13 C14 C9 C4 -178.16(18) . . . . ? N2 C4 C9 C10 -113.7(2) . . . . ? C3 C4 C9 C10 8.1(3) . . . . ? N2 C4 C9 C14 64.5(2) . . . . ? C3 C4 C9 C14 -173.74(18) . . . . ? C5 C3 C2 N1 178.13(18) . . . . ? C4 C3 C2 N1 -7.9(3) . . . . ? C5 C3 C2 C8 -2.0(4) . . . . ? C4 C3 C2 C8 172.0(2) . . . . ? C1 N1 C2 C3 -19.1(3) . . . . ? C1 N1 C2 C8 161.0(2) . . . . ? C15 O5 C13 C14 3.2(4) . . . . ? C15 O5 C13 C12 -176.9(2) . . . . ? C9 C14 C13 O5 180.0(2) . . . . ? C9 C14 C13 C12 0.1(3) . . . . ? C9 C10 C11 C12 0.0(3) . . . . ? C10 C11 C12 O4 179.7(2) . . . . ? C10 C11 C12 C13 0.2(4) . . . . ? O5 C13 C12 C11 179.9(2) . . . . ? C14 C13 C12 C11 -0.2(3) . . . . ? O5 C13 C12 O4 0.3(3) . . . . ? C14 C13 C12 O4 -179.8(2) . . . . ? C6A O3 C5 O2 -3.4(5) . . . . ? C6B O3 C5 O2 32.4(15) . . . . ? C6A O3 C5 C3 176.9(4) . . . . ? C6B O3 C5 C3 -147.3(14) . . . . ? C2 C3 C5 O2 7.4(4) . . . . ? C4 C3 C5 O2 -166.6(2) . . . . ? C2 C3 C5 O3 -173.0(2) . . . . ? C4 C3 C5 O3 13.0(3) . . . . ? C5 O3 C6A C7 -169.2(4) . . . . ? C6B O3 C6A C7 66.0(10) . . . . ? C5 O3 C6B C7 -138.5(8) . . . . ? C6A O3 C6B C7 -64.2(14) . . . . ? O3 C6B C7 C6A 59.4(16) . . . . ? O3 C6A C7 C6B -72.6(11) . . . . ? #===END