# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'PANDA, PRADEEPTA' _publ_contact_author_email pkpsc@uohyd.ernet.in _publ_section_title ; Meso-diacylated calix[4]pyrrole: Structural diversities and enhanced binding towards dihydrogenphosphate ion ; loop_ _publ_author_name S.Mahanta B.Sathish P.PANDA data_4 #TrackingRef '- pkp-cif.cif' _database_code_depnum_ccdc_archive 'CCDC 804419' #TrackingRef '- CisDCM.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H38 Cl2 N4 O2' _chemical_formula_weight 569.55 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.2397(12) _cell_length_b 12.4463(13) _cell_length_c 24.466(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.040(13) _cell_angle_gamma 90.00 _cell_volume 3060.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1688 _cell_measurement_theta_min 2.5996 _cell_measurement_theta_max 24.9691 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 0.246 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9389 _exptl_absorpt_correction_T_max 0.9688 _exptl_absorpt_process_details 'SCALE3 ABSPACK' _exptl_special_details ; Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23447 _diffrn_reflns_av_R_equivalents 0.2627 _diffrn_reflns_av_sigmaI/netI 0.3525 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 25.02 _reflns_number_total 5395 _reflns_number_gt 1444 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrysAlisPro _computing_cell_refinement CrysAlisPro _computing_data_reduction CrysAlisPro _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics OLEX2 _computing_publication_material OLEX2 _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^)+(0.0601P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5395 _refine_ls_number_parameters 372 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2934 _refine_ls_R_factor_gt 0.0810 _refine_ls_wR_factor_ref 0.1881 _refine_ls_wR_factor_gt 0.1351 _refine_ls_goodness_of_fit_ref 0.817 _refine_ls_restrained_S_all 0.817 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.0999(6) 0.5843(5) 0.3518(3) 0.0390(17) Uani 1 1 d . . . C2 C 1.1119(8) 0.5154(6) 0.3948(3) 0.070(2) Uani 1 1 d . . . H2 H 1.1266 0.4419 0.3932 0.084 Uiso 1 1 calc R . . C3 C 1.0984(8) 0.5742(6) 0.4432(3) 0.068(2) Uani 1 1 d . . . H3 H 1.1013 0.5460 0.4786 0.081 Uiso 1 1 calc R . . C4 C 1.0807(6) 0.6782(5) 0.4285(3) 0.0368(17) Uani 1 1 d . . . C5 C 1.0484(7) 0.7767(5) 0.4603(3) 0.0402(17) Uani 1 1 d . . . C6 C 0.9042(7) 0.8030(5) 0.4446(2) 0.0362(17) Uani 1 1 d . . . C7 C 0.8353(7) 0.8949(5) 0.4317(3) 0.0469(19) Uani 1 1 d . . . H7 H 0.8721 0.9631 0.4311 0.056 Uiso 1 1 calc R . . C8 C 0.6982(7) 0.8705(6) 0.4193(3) 0.0473(19) Uani 1 1 d . . . H8 H 0.6295 0.9197 0.4092 0.057 Uiso 1 1 calc R . . C9 C 0.6837(7) 0.7627(6) 0.4246(3) 0.0425(18) Uani 1 1 d . . . C10 C 0.5609(7) 0.6921(6) 0.4192(3) 0.056(2) Uani 1 1 d . . . C11 C 0.5711(6) 0.6018(6) 0.3779(3) 0.0395(17) Uani 1 1 d . . . C12 C 0.5452(7) 0.4971(6) 0.3802(3) 0.059(2) Uani 1 1 d . . . H12 H 0.5224 0.4607 0.4102 0.071 Uiso 1 1 calc R . . C13 C 0.5587(7) 0.4506(5) 0.3277(3) 0.055(2) Uani 1 1 d . . . H13 H 0.5474 0.3786 0.3179 0.066 Uiso 1 1 calc R . . C14 C 0.5906(6) 0.5302(5) 0.2954(3) 0.0349(17) Uani 1 1 d . . . C15 C 0.6077(6) 0.5317(5) 0.2356(3) 0.0354(17) Uani 1 1 d . . . C16 C 0.7451(7) 0.5693(4) 0.2305(3) 0.0325(16) Uani 1 1 d . . . C17 C 0.7927(7) 0.6122(5) 0.1875(3) 0.0460(18) Uani 1 1 d . . . H17 H 0.7416 0.6317 0.1533 0.055 Uiso 1 1 calc R . . C18 C 0.9317(8) 0.6226(5) 0.2025(3) 0.055(2) Uani 1 1 d . . . H18 H 0.9878 0.6507 0.1803 0.066 Uiso 1 1 calc R . . C19 C 0.9696(7) 0.5839(5) 0.2555(3) 0.0373(17) Uani 1 1 d . . . C20 C 1.1043(7) 0.5676(5) 0.2912(3) 0.0456(18) Uani 1 1 d . . . C21 C 1.1310(6) 0.8765(5) 0.4485(3) 0.061(2) Uani 1 1 d . . . H21A H 1.1094 0.8940 0.4096 0.091 Uiso 1 1 calc R . . H21B H 1.2242 0.8605 0.4587 0.091 Uiso 1 1 calc R . . H21C H 1.1101 0.9365 0.4700 0.091 Uiso 1 1 calc R . . C22 C 1.0895(8) 0.7535(6) 0.5231(3) 0.064(2) Uani 1 1 d . . . C23 C 1.2339(8) 0.7340(8) 0.5467(3) 0.125(4) Uani 1 1 d . . . H23A H 1.2420 0.6801 0.5752 0.188 Uiso 1 1 calc R . . H23B H 1.2743 0.7995 0.5624 0.188 Uiso 1 1 calc R . . H23C H 1.2779 0.7100 0.5176 0.188 Uiso 1 1 calc R . . C24 C 0.5511(8) 0.6427(6) 0.4755(3) 0.095(3) Uani 1 1 d . . . H24A H 0.4703 0.6020 0.4719 0.143 Uiso 1 1 calc R . . H24B H 0.5511 0.6988 0.5024 0.143 Uiso 1 1 calc R . . H24C H 0.6259 0.5962 0.4875 0.143 Uiso 1 1 calc R . . C25 C 0.4389(7) 0.7608(6) 0.3971(3) 0.086(3) Uani 1 1 d . . . H25A H 0.4481 0.7928 0.3624 0.129 Uiso 1 1 calc R . . H25B H 0.4310 0.8162 0.4236 0.129 Uiso 1 1 calc R . . H25C H 0.3607 0.7165 0.3915 0.129 Uiso 1 1 calc R . . C26 C 0.5036(6) 0.6051(5) 0.1998(3) 0.054(2) Uani 1 1 d . . . H26A H 0.5116 0.6766 0.2148 0.081 Uiso 1 1 calc R . . H26B H 0.4159 0.5781 0.2001 0.081 Uiso 1 1 calc R . . H26C H 0.5184 0.6063 0.1622 0.081 Uiso 1 1 calc R . . C27 C 0.5864(8) 0.4160(5) 0.2133(3) 0.0447(19) Uani 1 1 d . . . C28 C 0.7017(7) 0.3403(4) 0.2202(3) 0.060(2) Uani 1 1 d . . . H28A H 0.7456 0.3389 0.2585 0.090 Uiso 1 1 calc R . . H28B H 0.7631 0.3639 0.1975 0.090 Uiso 1 1 calc R . . H28C H 0.6704 0.2696 0.2089 0.090 Uiso 1 1 calc R . . C30 C 1.2069(6) 0.6450(6) 0.2730(3) 0.066(2) Uani 1 1 d . . . H30A H 1.2108 0.6320 0.2347 0.100 Uiso 1 1 calc R . . H30B H 1.2931 0.6328 0.2957 0.100 Uiso 1 1 calc R . . H30C H 1.1804 0.7180 0.2774 0.100 Uiso 1 1 calc R . . C31 C 0.2250(7) 0.6419(5) 0.0745(3) 0.075(2) Uani 1 1 d . . . H31A H 0.2493 0.6686 0.0405 0.090 Uiso 1 1 calc R . . H31B H 0.2970 0.5968 0.0933 0.090 Uiso 1 1 calc R . . C29C C 1.1505(7) 0.4517(5) 0.2826(3) 0.079(3) Uani 1 1 d . . . H29A H 1.0963 0.4019 0.2983 0.118 Uiso 1 1 calc R . . H29B H 1.2418 0.4435 0.3007 0.118 Uiso 1 1 calc R . . H29C H 1.1420 0.4378 0.2435 0.118 Uiso 1 1 calc R . . Cl1 Cl 0.2046(2) 0.74950(16) 0.11703(8) 0.0960(8) Uani 1 1 d . . . Cl2 Cl 0.0844(3) 0.56711(18) 0.05795(12) 0.1270(11) Uani 1 1 d . . . H4A H 0.856(7) 0.529(5) 0.306(3) 0.083 Uiso 1 1 d . . . H3A H 0.607(7) 0.686(5) 0.314(3) 0.083 Uiso 1 1 d . . . H1A H 1.044(7) 0.729(5) 0.353(3) 0.083 Uiso 1 1 d . . . H2A H 0.828(7) 0.655(5) 0.447(3) 0.083 Uiso 1 1 d . . . N3 N 0.5972(5) 0.6232(4) 0.3258(2) 0.0422(16) Uani 1 1 d . . . N2 N 0.8097(6) 0.7222(4) 0.4397(2) 0.0413(16) Uani 1 1 d . . . N1 N 1.0808(5) 0.6845(4) 0.3727(2) 0.0382(15) Uani 1 1 d . . . N4 N 0.8550(6) 0.5526(4) 0.2723(2) 0.0357(14) Uani 1 1 d . . . O2 O 0.4774(5) 0.3879(4) 0.1913(2) 0.0725(16) Uani 1 1 d . . . O1 O 1.0095(6) 0.7588(6) 0.5527(2) 0.114(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.041(5) 0.044(4) 0.033(4) 0.003(4) 0.009(4) 0.007(4) C2 0.102(7) 0.050(5) 0.064(6) 0.003(5) 0.032(5) 0.021(4) C3 0.104(7) 0.071(6) 0.031(5) 0.017(4) 0.018(5) 0.018(5) C4 0.034(4) 0.053(5) 0.023(4) 0.003(4) 0.006(4) 0.005(4) C5 0.039(5) 0.051(5) 0.032(4) -0.012(4) 0.009(4) 0.006(4) C6 0.033(5) 0.045(4) 0.032(4) -0.009(3) 0.009(4) -0.002(4) C7 0.044(5) 0.049(5) 0.052(5) 0.000(4) 0.021(4) 0.002(4) C8 0.033(5) 0.064(5) 0.045(5) 0.004(4) 0.007(4) 0.025(4) C9 0.035(5) 0.056(5) 0.040(4) -0.011(4) 0.014(4) 0.003(4) C10 0.032(5) 0.074(5) 0.064(6) -0.029(5) 0.016(5) -0.003(4) C11 0.032(4) 0.057(5) 0.033(5) -0.010(4) 0.013(4) -0.008(4) C12 0.080(6) 0.060(5) 0.048(5) 0.002(4) 0.038(5) 0.001(4) C13 0.072(6) 0.035(4) 0.059(5) -0.008(4) 0.015(5) -0.010(4) C14 0.036(5) 0.034(4) 0.034(4) -0.004(4) 0.004(4) -0.005(3) C15 0.033(5) 0.041(4) 0.036(4) -0.006(3) 0.015(4) -0.005(3) C16 0.032(5) 0.040(4) 0.026(4) 0.002(3) 0.008(4) 0.005(3) C17 0.047(5) 0.069(5) 0.023(4) -0.001(4) 0.007(4) -0.009(4) C18 0.059(6) 0.060(5) 0.047(6) -0.012(4) 0.016(5) -0.014(4) C19 0.037(5) 0.050(4) 0.024(4) -0.002(3) 0.007(4) 0.002(4) C20 0.039(5) 0.069(5) 0.029(4) -0.011(4) 0.008(4) 0.007(4) C21 0.037(4) 0.073(5) 0.075(6) -0.028(4) 0.014(4) -0.008(4) C22 0.044(6) 0.104(6) 0.047(5) -0.012(5) 0.016(5) 0.017(5) C23 0.064(7) 0.247(11) 0.051(6) -0.040(7) -0.023(5) 0.061(7) C24 0.094(7) 0.136(7) 0.078(6) -0.055(6) 0.070(6) -0.071(6) C25 0.034(5) 0.104(6) 0.122(7) -0.076(6) 0.020(5) -0.007(5) C26 0.037(5) 0.071(5) 0.052(5) 0.001(4) 0.003(4) 0.008(4) C27 0.055(5) 0.049(5) 0.035(5) -0.011(4) 0.022(4) -0.018(4) C28 0.059(5) 0.038(4) 0.084(6) -0.008(4) 0.019(5) 0.009(4) C30 0.037(5) 0.128(7) 0.039(5) -0.017(4) 0.019(4) -0.023(5) C31 0.066(6) 0.076(5) 0.079(6) -0.016(5) 0.002(5) 0.000(5) C29C 0.074(6) 0.084(6) 0.071(6) -0.021(5) -0.004(5) 0.042(5) Cl1 0.137(2) 0.0794(14) 0.0746(15) -0.0092(13) 0.0279(15) -0.0180(15) Cl2 0.129(2) 0.0932(18) 0.172(3) -0.0288(17) 0.062(2) -0.0437(16) N3 0.039(4) 0.048(4) 0.043(4) -0.004(4) 0.016(3) -0.005(3) N2 0.029(4) 0.043(4) 0.049(4) -0.009(3) 0.000(3) 0.001(4) N1 0.029(4) 0.047(4) 0.039(4) 0.001(3) 0.008(3) 0.008(3) N4 0.028(3) 0.051(4) 0.031(4) 0.005(3) 0.014(4) 0.003(3) O2 0.068(4) 0.074(4) 0.075(4) -0.036(3) 0.011(4) -0.018(3) O1 0.071(5) 0.232(7) 0.040(3) 0.024(4) 0.010(3) 0.031(5) _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 C1 C2 1.345(8) . ? C1 N1 1.376(7) . ? C1 C20 1.505(8) . ? C2 C3 1.420(8) . ? C3 C4 1.346(8) . ? C4 N1 1.367(7) . ? C4 C5 1.521(8) . ? C5 C6 1.489(8) . ? C5 C22 1.541(9) . ? C5 C21 1.560(8) . ? C6 C7 1.350(7) . ? C6 N2 1.386(7) . ? C7 C8 1.411(8) . ? C8 C9 1.359(7) . ? C9 N2 1.369(7) . ? C9 C10 1.518(9) . ? C10 C25 1.525(8) . ? C10 C11 1.528(8) . ? C10 C24 1.528(9) . ? C11 C12 1.333(8) . ? C11 N3 1.379(7) . ? C12 C13 1.439(8) . ? C13 C14 1.345(8) . ? C14 N3 1.371(7) . ? C14 C15 1.508(8) . ? C15 C16 1.510(8) . ? C15 C27 1.540(8) . ? C15 C26 1.543(7) . ? C16 C17 1.351(7) . ? C16 N4 1.385(7) . ? C17 C18 1.406(8) . ? C18 C19 1.369(8) . ? C19 N4 1.372(7) . ? C19 C20 1.499(8) . ? C20 C29C 1.545(8) . ? C20 C30 1.552(8) . ? C22 O1 1.194(7) . ? C22 C23 1.501(9) . ? C27 O2 1.196(7) . ? C27 C28 1.494(8) . ? C31 Cl2 1.697(7) . ? C31 Cl1 1.733(7) . ? 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 C2 C1 N1 106.5(6) . . ? C2 C1 C20 131.8(6) . . ? N1 C1 C20 121.7(6) . . ? C1 C2 C3 108.4(6) . . ? C4 C3 C2 107.6(6) . . ? C3 C4 N1 107.2(6) . . ? C3 C4 C5 132.0(6) . . ? N1 C4 C5 120.4(6) . . ? C6 C5 C4 110.3(5) . . ? C6 C5 C22 111.5(6) . . ? C4 C5 C22 108.4(5) . . ? C6 C5 C21 108.8(5) . . ? C4 C5 C21 111.7(5) . . ? C22 C5 C21 106.2(5) . . ? C7 C6 N2 105.6(6) . . ? C7 C6 C5 134.0(6) . . ? N2 C6 C5 120.3(6) . . ? C6 C7 C8 108.8(6) . . ? C9 C8 C7 108.4(6) . . ? C8 C9 N2 106.0(6) . . ? C8 C9 C10 131.8(7) . . ? N2 C9 C10 122.1(6) . . ? C9 C10 C25 108.4(6) . . ? C9 C10 C11 108.8(6) . . ? C25 C10 C11 109.4(6) . . ? C9 C10 C24 110.5(6) . . ? C25 C10 C24 110.7(6) . . ? C11 C10 C24 108.9(6) . . ? C12 C11 N3 107.7(6) . . ? C12 C11 C10 130.7(7) . . ? N3 C11 C10 121.3(6) . . ? C11 C12 C13 107.6(6) . . ? C14 C13 C12 107.7(6) . . ? C13 C14 N3 107.2(6) . . ? C13 C14 C15 131.8(6) . . ? N3 C14 C15 120.8(6) . . ? C14 C15 C16 111.6(5) . . ? C14 C15 C27 107.2(5) . . ? C16 C15 C27 109.4(5) . . ? C14 C15 C26 111.2(5) . . ? C16 C15 C26 108.8(5) . . ? C27 C15 C26 108.5(5) . . ? C17 C16 N4 105.7(6) . . ? C17 C16 C15 131.9(6) . . ? N4 C16 C15 122.0(6) . . ? C16 C17 C18 109.4(6) . . ? C19 C18 C17 107.7(7) . . ? C18 C19 N4 106.3(6) . . ? C18 C19 C20 131.5(7) . . ? N4 C19 C20 122.1(6) . . ? C19 C20 C1 110.9(6) . . ? C19 C20 C29C 108.6(5) . . ? C1 C20 C29C 109.3(6) . . ? C19 C20 C30 110.3(5) . . ? C1 C20 C30 110.3(5) . . ? C29C C20 C30 107.4(6) . . ? O1 C22 C23 121.0(7) . . ? O1 C22 C5 120.4(7) . . ? C23 C22 C5 118.3(7) . . ? O2 C27 C28 121.0(6) . . ? O2 C27 C15 119.3(7) . . ? C28 C27 C15 119.6(6) . . ? Cl2 C31 Cl1 111.9(4) . . ? C14 N3 C11 109.8(5) . . ? C9 N2 C6 111.3(5) . . ? C4 N1 C1 110.3(5) . . ? C19 N4 C16 110.9(5) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.530 _refine_diff_density_min -0.464 _refine_diff_density_rms 0.054 data_3 #TrackingRef '- pkp-cif.cif' _database_code_depnum_ccdc_archive 'CCDC 804420' #TrackingRef '- ciswater.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H38 N4 O3' _chemical_formula_weight 502.64 _chemical_absolute_configuration unk loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.309(7) _cell_length_b 13.246(9) _cell_length_c 11.386(8) _cell_angle_alpha 90.00 _cell_angle_beta 113.540(11) _cell_angle_gamma 90.00 _cell_volume 1425.6(18) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5463 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 28.18 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.171 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 540 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9804 _exptl_absorpt_correction_T_max 0.9864 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13621 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 25.03 _reflns_number_total 5030 _reflns_number_gt 4941 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0398P)^2^+1.2467P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(3) _refine_ls_number_reflns 5030 _refine_ls_number_parameters 362 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0825 _refine_ls_R_factor_gt 0.0807 _refine_ls_wR_factor_ref 0.1632 _refine_ls_wR_factor_gt 0.1624 _refine_ls_goodness_of_fit_ref 1.302 _refine_ls_restrained_S_all 1.302 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2773(4) 0.0213(3) 0.4079(3) 0.0285(8) Uani 1 1 d . . . C2 C 0.2057(4) -0.0643(3) 0.3977(4) 0.0366(10) Uani 1 1 d . . . H2 H 0.2430 -0.1290 0.4041 0.044 Uiso 1 1 calc R . . C3 C 0.0654(4) -0.0412(3) 0.3759(4) 0.0374(10) Uani 1 1 d . . . H3 H -0.0069 -0.0872 0.3641 0.045 Uiso 1 1 calc R . . C4 C 0.0550(4) 0.0603(3) 0.3754(4) 0.0303(9) Uani 1 1 d . . . C5 C -0.0660(4) 0.1275(3) 0.3731(4) 0.0387(10) Uani 1 1 d . . . C6 C -0.0804(4) 0.2215(3) 0.2931(4) 0.0330(9) Uani 1 1 d . . . C7 C -0.1063(5) 0.3189(3) 0.3111(4) 0.0393(10) Uani 1 1 d . . . H7 H -0.1123 0.3453 0.3845 0.047 Uiso 1 1 calc R . . C8 C -0.1227(4) 0.3738(3) 0.2002(4) 0.0397(10) Uani 1 1 d . . . H8 H -0.1432 0.4423 0.1865 0.048 Uiso 1 1 calc R . . C9 C -0.1031(4) 0.3085(3) 0.1172(4) 0.0294(9) Uani 1 1 d . . . C10 C -0.1144(4) 0.3208(3) -0.0205(4) 0.0344(9) Uani 1 1 d . . . C11 C 0.0118(4) 0.2790(3) -0.0397(4) 0.0315(9) Uani 1 1 d . . . C12 C 0.0214(5) 0.2432(4) -0.1471(4) 0.0452(12) Uani 1 1 d . . . H12 H -0.0537 0.2333 -0.2257 0.054 Uiso 1 1 calc R . . C13 C 0.1644(5) 0.2236(4) -0.1195(4) 0.0516(12) Uani 1 1 d . . . H13 H 0.1999 0.1958 -0.1756 0.062 Uiso 1 1 calc R . . C14 C 0.2419(4) 0.2521(3) 0.0031(4) 0.0362(10) Uani 1 1 d . . . C15 C 0.4004(4) 0.2600(4) 0.0773(4) 0.0433(11) Uani 1 1 d . . . C16 C 0.4439(4) 0.2328(3) 0.2166(4) 0.0330(9) Uani 1 1 d . . . C17 C 0.5348(4) 0.2770(3) 0.3249(4) 0.0401(10) Uani 1 1 d . . . H17 H 0.5818 0.3379 0.3306 0.048 Uiso 1 1 calc R . . C18 C 0.5452(4) 0.2136(3) 0.4280(4) 0.0329(9) Uani 1 1 d . . . H18 H 0.6009 0.2255 0.5140 0.040 Uiso 1 1 calc R . . C19 C 0.4611(4) 0.1332(3) 0.3805(4) 0.0263(8) Uani 1 1 d . . . C20 C 0.4353(4) 0.0379(3) 0.4430(4) 0.0322(9) Uani 1 1 d . . . C21 C -0.0384(6) 0.1586(5) 0.5109(5) 0.0674(17) Uani 1 1 d . . . H21A H 0.0480 0.1966 0.5464 0.101 Uiso 1 1 calc R . . H21B H -0.0303 0.0993 0.5618 0.101 Uiso 1 1 calc R . . H21C H -0.1154 0.1994 0.5108 0.101 Uiso 1 1 calc R . . C22 C -0.2036(5) 0.0668(4) 0.3164(6) 0.0596(15) Uani 1 1 d . . . H22A H -0.2810 0.1078 0.3147 0.089 Uiso 1 1 calc R . . H22B H -0.1961 0.0081 0.3681 0.089 Uiso 1 1 calc R . . H22C H -0.2198 0.0463 0.2308 0.089 Uiso 1 1 calc R . . C23 C -0.2493(5) 0.2683(4) -0.1118(4) 0.0511(12) Uani 1 1 d . . . H23A H -0.2595 0.2782 -0.1986 0.077 Uiso 1 1 calc R . . H23B H -0.3297 0.2964 -0.1010 0.077 Uiso 1 1 calc R . . H23C H -0.2432 0.1974 -0.0931 0.077 Uiso 1 1 calc R . . C24 C -0.1323(6) 0.4359(4) -0.0470(4) 0.0491(12) Uani 1 1 d . . . C25 C -0.0017(8) 0.4987(4) -0.0111(7) 0.084(2) Uani 1 1 d . . . H25A H -0.0260 0.5688 -0.0132 0.126 Uiso 1 1 calc R . . H25B H 0.0412 0.4867 -0.0708 0.126 Uiso 1 1 calc R . . H25C H 0.0638 0.4810 0.0737 0.126 Uiso 1 1 calc R . . C26 C 0.4457(7) 0.3690(5) 0.0677(6) 0.082(2) Uani 1 1 d . . . H26A H 0.4206 0.3861 -0.0206 0.123 Uiso 1 1 calc R . . H26B H 0.5462 0.3752 0.1138 0.123 Uiso 1 1 calc R . . H26C H 0.3985 0.4140 0.1039 0.123 Uiso 1 1 calc R . . C27 C 0.4739(6) 0.1880(6) 0.0170(6) 0.0762(19) Uani 1 1 d . . . H27A H 0.4446 0.1199 0.0220 0.114 Uiso 1 1 calc R . . H27B H 0.5746 0.1932 0.0625 0.114 Uiso 1 1 calc R . . H27C H 0.4483 0.2059 -0.0711 0.114 Uiso 1 1 calc R . . C28 C 0.4984(5) -0.0527(3) 0.4010(4) 0.0391(10) Uani 1 1 d . . . H28A H 0.4527 -0.0602 0.3097 0.059 Uiso 1 1 calc R . . H28B H 0.4843 -0.1127 0.4417 0.059 Uiso 1 1 calc R . . H28C H 0.5979 -0.0420 0.4253 0.059 Uiso 1 1 calc R . . C29 C 0.5116(5) 0.0515(4) 0.5901(5) 0.0458(11) Uani 1 1 d . . . C30 C 0.4438(5) 0.1142(5) 0.6584(5) 0.0676(16) Uani 1 1 d . . . H30A H 0.3654 0.0780 0.6633 0.101 Uiso 1 1 calc R . . H30B H 0.4106 0.1762 0.6126 0.101 Uiso 1 1 calc R . . H30C H 0.5116 0.1287 0.7433 0.101 Uiso 1 1 calc R . . H1A H 0.206(5) 0.162(4) 0.388(4) 0.044 Uiso 1 1 d . . . H2A H -0.059(5) 0.169(4) 0.138(5) 0.044 Uiso 1 1 d . . . H3A H 0.171(5) 0.303(4) 0.128(5) 0.044 Uiso 1 1 d . . . H4A H 0.347(5) 0.104(4) 0.203(4) 0.044 Uiso 1 1 d . . . H3C H 0.265(7) 0.376(5) 0.349(6) 0.069(19) Uiso 1 1 d . . . N1 N 0.1856(3) 0.0989(2) 0.3948(3) 0.0282(7) Uani 1 1 d . . . N2 N -0.0780(3) 0.2158(3) 0.1745(3) 0.0307(8) Uani 1 1 d . . . N3 N 0.1467(4) 0.2852(3) 0.0511(3) 0.0337(8) Uani 1 1 d . . . N4 N 0.3977(3) 0.1453(3) 0.2512(3) 0.0334(8) Uani 1 1 d . . . O1 O -0.2456(5) 0.4723(3) -0.0949(4) 0.0787(13) Uani 1 1 d . . . O2 O 0.6219(4) 0.0106(3) 0.6468(3) 0.0702(11) Uani 1 1 d . . . O3 O 0.2163(4) 0.3226(3) 0.3365(5) 0.0668(11) Uani 1 1 d . . . H3B H 0.216(8) 0.335(6) 0.413(8) 0.11(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0262(19) 0.030(2) 0.028(2) 0.0074(17) 0.0098(16) 0.0018(16) C2 0.036(2) 0.030(2) 0.042(2) 0.0110(19) 0.0139(19) 0.0099(18) C3 0.025(2) 0.043(3) 0.046(3) 0.012(2) 0.0162(19) -0.0036(18) C4 0.032(2) 0.033(2) 0.028(2) 0.0087(17) 0.0139(18) -0.0021(17) C5 0.034(2) 0.052(3) 0.041(2) 0.012(2) 0.026(2) 0.011(2) C6 0.0235(19) 0.048(2) 0.031(2) -0.0022(18) 0.0149(16) 0.0059(18) C7 0.044(2) 0.045(3) 0.034(2) -0.008(2) 0.021(2) 0.009(2) C8 0.037(2) 0.034(2) 0.051(3) 0.003(2) 0.021(2) 0.0097(19) C9 0.025(2) 0.028(2) 0.034(2) 0.0055(17) 0.0113(17) 0.0082(16) C10 0.032(2) 0.037(2) 0.029(2) 0.0102(18) 0.0069(17) 0.0052(17) C11 0.036(2) 0.030(2) 0.025(2) 0.0061(16) 0.0092(17) 0.0011(17) C12 0.046(3) 0.061(3) 0.021(2) 0.006(2) 0.0042(19) 0.009(2) C13 0.054(3) 0.072(3) 0.039(3) 0.008(2) 0.029(2) 0.018(3) C14 0.038(2) 0.041(2) 0.037(2) 0.0116(19) 0.0235(19) 0.0036(19) C15 0.033(2) 0.063(3) 0.042(2) 0.012(2) 0.0225(19) 0.002(2) C16 0.0221(18) 0.025(2) 0.055(3) 0.0019(18) 0.0189(19) -0.0006(16) C17 0.031(2) 0.027(2) 0.061(3) 0.000(2) 0.018(2) 0.0002(18) C18 0.027(2) 0.030(2) 0.036(2) -0.0081(18) 0.0069(17) -0.0003(17) C19 0.0155(17) 0.033(2) 0.028(2) -0.0066(16) 0.0070(15) 0.0061(15) C20 0.031(2) 0.030(2) 0.032(2) 0.0048(16) 0.0094(18) 0.0029(16) C21 0.083(4) 0.086(4) 0.050(3) 0.027(3) 0.044(3) 0.038(3) C22 0.034(3) 0.060(3) 0.094(4) 0.024(3) 0.035(3) 0.011(2) C23 0.044(3) 0.068(3) 0.039(3) 0.004(2) 0.014(2) 0.007(3) C24 0.073(3) 0.045(3) 0.034(2) 0.014(2) 0.027(2) 0.022(3) C25 0.113(5) 0.030(3) 0.143(6) 0.003(3) 0.087(5) -0.005(3) C26 0.067(4) 0.090(5) 0.085(4) 0.041(4) 0.026(3) -0.014(3) C27 0.052(3) 0.132(6) 0.058(3) 0.014(3) 0.036(3) 0.018(3) C28 0.034(2) 0.033(2) 0.048(3) 0.0033(19) 0.014(2) -0.0038(19) C29 0.036(3) 0.049(3) 0.050(3) 0.005(2) 0.014(2) -0.003(2) C30 0.050(3) 0.104(5) 0.045(3) -0.022(3) 0.015(3) -0.005(3) N1 0.0288(17) 0.0219(16) 0.0383(19) 0.0059(15) 0.0179(15) 0.0040(14) N2 0.0312(17) 0.0328(19) 0.0331(19) -0.0045(15) 0.0180(15) 0.0078(15) N3 0.038(2) 0.040(2) 0.0253(18) 0.0005(16) 0.0147(16) -0.0028(16) N4 0.0243(18) 0.035(2) 0.040(2) -0.0135(16) 0.0116(16) -0.0116(15) O1 0.083(3) 0.060(2) 0.071(3) 0.020(2) 0.007(2) 0.043(2) O2 0.049(2) 0.083(3) 0.058(2) 0.004(2) -0.0013(17) 0.017(2) O3 0.050(2) 0.067(3) 0.081(3) -0.021(2) 0.023(2) -0.020(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 C1 C2 1.332(6) . ? C1 N1 1.364(5) . ? C1 C20 1.531(5) . ? C2 C3 1.400(6) . ? C3 C4 1.348(6) . ? C4 N1 1.373(5) . ? C4 C5 1.525(6) . ? C5 C6 1.515(6) . ? C5 C22 1.531(7) . ? C5 C21 1.535(7) . ? C6 C7 1.350(6) . ? C6 N2 1.362(5) . ? C7 C8 1.408(6) . ? C8 C9 1.355(6) . ? C9 N2 1.366(5) . ? C9 C10 1.534(6) . ? C10 C11 1.509(6) . ? C10 C23 1.531(6) . ? C10 C24 1.550(6) . ? C11 C12 1.351(6) . ? C11 N3 1.365(5) . ? C12 C13 1.403(6) . ? C13 C14 1.356(7) . ? C14 N3 1.373(5) . ? C14 C15 1.513(6) . ? C15 C16 1.510(6) . ? C15 C26 1.535(8) . ? C15 C27 1.540(8) . ? C16 C17 1.349(6) . ? C16 N4 1.370(5) . ? C17 C18 1.412(6) . ? C18 C19 1.343(5) . ? C19 N4 1.360(5) . ? C19 C20 1.524(6) . ? C20 C28 1.530(6) . ? C20 C29 1.550(6) . ? C24 O1 1.177(6) . ? C24 C25 1.495(8) . ? C29 O2 1.191(5) . ? C29 C30 1.489(7) . ? 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 C2 C1 N1 107.2(3) . . ? C2 C1 C20 129.8(4) . . ? N1 C1 C20 122.6(3) . . ? C1 C2 C3 109.1(4) . . ? C4 C3 C2 107.1(4) . . ? C3 C4 N1 107.5(4) . . ? C3 C4 C5 130.2(4) . . ? N1 C4 C5 121.8(4) . . ? C6 C5 C4 111.9(3) . . ? C6 C5 C22 109.1(4) . . ? C4 C5 C22 108.3(4) . . ? C6 C5 C21 109.1(4) . . ? C4 C5 C21 108.8(3) . . ? C22 C5 C21 109.6(4) . . ? C7 C6 N2 106.7(4) . . ? C7 C6 C5 132.2(4) . . ? N2 C6 C5 121.0(4) . . ? C6 C7 C8 108.5(4) . . ? C9 C8 C7 107.3(4) . . ? C8 C9 N2 107.1(4) . . ? C8 C9 C10 132.3(4) . . ? N2 C9 C10 120.5(3) . . ? C11 C10 C23 109.6(4) . . ? C11 C10 C9 113.0(3) . . ? C23 C10 C9 108.9(3) . . ? C11 C10 C24 112.1(4) . . ? C23 C10 C24 108.0(4) . . ? C9 C10 C24 105.0(3) . . ? C12 C11 N3 106.6(4) . . ? C12 C11 C10 129.8(4) . . ? N3 C11 C10 123.0(3) . . ? C11 C12 C13 108.2(4) . . ? C14 C13 C12 108.3(4) . . ? C13 C14 N3 106.1(4) . . ? C13 C14 C15 130.9(4) . . ? N3 C14 C15 122.7(4) . . ? C16 C15 C14 111.8(3) . . ? C16 C15 C26 109.1(4) . . ? C14 C15 C26 108.5(4) . . ? C16 C15 C27 109.1(4) . . ? C14 C15 C27 108.8(4) . . ? C26 C15 C27 109.5(4) . . ? C17 C16 N4 107.4(4) . . ? C17 C16 C15 131.6(4) . . ? N4 C16 C15 120.8(4) . . ? C16 C17 C18 107.2(4) . . ? C19 C18 C17 108.3(4) . . ? C18 C19 N4 107.2(4) . . ? C18 C19 C20 132.4(4) . . ? N4 C19 C20 120.3(3) . . ? C19 C20 C28 109.2(3) . . ? C19 C20 C1 111.3(3) . . ? C28 C20 C1 110.3(3) . . ? C19 C20 C29 107.5(3) . . ? C28 C20 C29 109.5(3) . . ? C1 C20 C29 109.1(3) . . ? O1 C24 C25 121.2(5) . . ? O1 C24 C10 120.8(5) . . ? C25 C24 C10 118.0(4) . . ? O2 C29 C30 121.1(5) . . ? O2 C29 C20 119.7(4) . . ? C30 C29 C20 119.2(4) . . ? C1 N1 C4 109.2(3) . . ? C6 N2 C9 110.4(3) . . ? C11 N3 C14 110.7(4) . . ? C19 N4 C16 109.8(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.240 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.052 data_2 #TrackingRef '- pkp-cif.cif' _database_code_depnum_ccdc_archive 'CCDC 804421' #TrackingRef '- transI4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H36 N4 O2' _chemical_formula_weight 484.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M 'I4(1)/a ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' _cell_length_a 21.3560(19) _cell_length_b 21.3560(19) _cell_length_c 11.329(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5167.0(12) _cell_formula_units_Z 8 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 4162 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 23.09 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2080 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9797 _exptl_absorpt_correction_T_max 0.9890 _exptl_absorpt_process_details 'SCALE3 ABSPACK' _exptl_special_details ; Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17738 _diffrn_reflns_av_R_equivalents 0.0768 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 24.71 _reflns_number_total 2203 _reflns_number_gt 1913 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrysAlisPro _computing_cell_refinement CrysAlisPro _computing_data_reduction CrysAlisPro _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics OLEX2 _computing_publication_material OLEX2 _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^)+(0.0497P)^2^+20.2322P] 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 2203 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1238 _refine_ls_R_factor_gt 0.1076 _refine_ls_wR_factor_ref 0.2133 _refine_ls_wR_factor_gt 0.2051 _refine_ls_goodness_of_fit_ref 1.234 _refine_ls_restrained_S_all 1.234 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N2 N 0.53628(17) 0.42261(17) 0.1281(3) 0.0379(9) Uani 1 1 d . . . N1 N 0.41620(18) 0.52075(17) 0.1229(3) 0.0390(9) Uani 1 1 d . . . C6 C 0.49167(18) 0.39408(18) 0.1965(3) 0.0311(9) Uani 1 1 d . . . C4 C 0.39967(19) 0.46518(18) 0.1764(4) 0.0341(10) Uani 1 1 d . . . C5 C 0.4414(2) 0.42968(19) 0.2613(4) 0.0378(10) Uani 1 1 d . . . C9 C 0.5749(2) 0.37906(18) 0.0772(4) 0.0364(10) Uani 1 1 d . . . C1 C 0.36819(19) 0.54183(19) 0.0522(4) 0.0381(10) Uani 1 1 d . . . C3 C 0.3412(2) 0.4522(2) 0.1368(4) 0.0467(12) Uani 1 1 d . . . H3 H 0.3177 0.4172 0.1574 0.056 Uiso 1 1 calc R . . C2 C 0.3219(2) 0.4996(2) 0.0604(4) 0.0459(12) Uani 1 1 d . . . H2 H 0.2836 0.5015 0.0218 0.055 Uiso 1 1 calc R . . C11 C 0.6418(2) 0.3441(2) -0.0845(5) 0.0509(13) Uani 1 1 d . . . O1 O 0.68690(17) 0.30919(18) -0.0824(4) 0.0730(12) Uani 1 1 d . . . C8 C 0.5532(2) 0.32236(19) 0.1134(4) 0.0406(11) Uani 1 1 d . . . H8 H 0.5697 0.2837 0.0921 0.049 Uiso 1 1 calc R . . C13 C 0.4703(2) 0.4750(2) 0.3512(4) 0.0597(14) Uani 1 1 d . . . H13A H 0.4960 0.4521 0.4055 0.090 Uiso 1 1 calc R . . H13B H 0.4375 0.4960 0.3937 0.090 Uiso 1 1 calc R . . H13C H 0.4954 0.5054 0.3105 0.090 Uiso 1 1 calc R . . C7 C 0.5019(2) 0.33208(18) 0.1881(4) 0.0393(11) Uani 1 1 d . . . H7 H 0.4789 0.3010 0.2256 0.047 Uiso 1 1 calc R . . C10 C 0.6338(2) 0.3948(2) 0.0087(4) 0.0456(12) Uani 1 1 d . . . C12 C 0.4003(3) 0.3824(2) 0.3292(5) 0.0633(15) Uani 1 1 d . . . H12A H 0.3812 0.3539 0.2744 0.095 Uiso 1 1 calc R . . H12B H 0.3683 0.4045 0.3718 0.095 Uiso 1 1 calc R . . H12C H 0.4259 0.3593 0.3837 0.095 Uiso 1 1 calc R . . C15 C 0.5927(2) 0.3384(2) -0.1762(5) 0.0548(13) Uani 1 1 d . . . H15A H 0.6049 0.3618 -0.2448 0.082 Uiso 1 1 calc R . . H15B H 0.5539 0.3545 -0.1463 0.082 Uiso 1 1 calc R . . H15C H 0.5875 0.2951 -0.1971 0.082 Uiso 1 1 calc R . . C14 C 0.6909(2) 0.3915(3) 0.0954(5) 0.0576(14) Uani 1 1 d . . . H14A H 0.6870 0.4237 0.1541 0.086 Uiso 1 1 calc R . . H14B H 0.7291 0.3974 0.0520 0.086 Uiso 1 1 calc R . . H14C H 0.6917 0.3512 0.1332 0.086 Uiso 1 1 calc R . . H1A H 0.450(2) 0.5383(19) 0.140(4) 0.035(12) Uiso 1 1 d . . . H2A H 0.5425(19) 0.459(2) 0.123(4) 0.032(12) 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 N2 0.051(2) 0.0189(19) 0.044(2) 0.0011(17) 0.0116(18) 0.0000(16) N1 0.033(2) 0.036(2) 0.048(2) 0.0020(18) 0.0071(18) -0.0064(17) C6 0.037(2) 0.030(2) 0.026(2) 0.0053(17) 0.0011(18) 0.0000(17) C4 0.036(2) 0.027(2) 0.039(2) -0.0026(18) 0.017(2) -0.0008(17) C5 0.045(3) 0.036(2) 0.032(2) 0.0012(19) 0.012(2) 0.0008(19) C9 0.045(2) 0.031(2) 0.034(2) 0.0015(19) 0.002(2) 0.0076(18) C1 0.040(2) 0.035(2) 0.040(3) -0.002(2) 0.009(2) 0.0099(19) C3 0.045(3) 0.030(2) 0.064(3) 0.002(2) 0.005(2) -0.007(2) C2 0.035(2) 0.045(3) 0.058(3) 0.000(2) -0.002(2) 0.002(2) C11 0.055(3) 0.042(3) 0.056(3) 0.005(2) 0.017(3) 0.008(2) O1 0.059(2) 0.071(3) 0.089(3) 0.002(2) 0.013(2) 0.034(2) C8 0.054(3) 0.024(2) 0.043(3) -0.0010(19) 0.003(2) 0.0087(19) C13 0.069(4) 0.068(4) 0.042(3) -0.016(3) 0.005(3) 0.013(3) C7 0.051(3) 0.027(2) 0.040(2) 0.0079(19) 0.008(2) -0.0001(19) C10 0.042(3) 0.044(3) 0.051(3) 0.010(2) 0.007(2) 0.006(2) C12 0.068(4) 0.062(3) 0.060(3) 0.019(3) 0.030(3) 0.012(3) C15 0.070(3) 0.045(3) 0.049(3) -0.014(2) -0.005(3) 0.007(2) C14 0.043(3) 0.072(4) 0.057(3) 0.009(3) -0.009(2) -0.002(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 N2 C9 1.371(5) . ? N2 C6 1.371(5) . ? N1 C1 1.377(6) . ? N1 C4 1.378(5) . ? C6 C7 1.345(5) . ? C6 C5 1.507(6) . ? C4 C3 1.355(6) . ? C4 C5 1.515(6) . ? C5 C13 1.535(6) . ? C5 C12 1.543(6) . ? C9 C8 1.360(6) . ? C9 C10 1.515(6) . ? C1 C2 1.341(6) . ? C1 C10 1.519(6) 9_665 ? C3 C2 1.393(6) . ? C11 O1 1.218(5) . ? C11 C15 1.481(7) . ? C11 C10 1.523(7) . ? C8 C7 1.400(6) . ? C10 C1 1.519(6) 9_665 ? C10 C14 1.568(6) . ? 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 C9 N2 C6 110.8(3) . . ? C1 N1 C4 110.3(4) . . ? C7 C6 N2 106.5(4) . . ? C7 C6 C5 130.3(4) . . ? N2 C6 C5 123.1(3) . . ? C3 C4 N1 105.5(4) . . ? C3 C4 C5 130.5(4) . . ? N1 C4 C5 124.0(4) . . ? C6 C5 C4 111.2(3) . . ? C6 C5 C13 110.8(4) . . ? C4 C5 C13 110.0(4) . . ? C6 C5 C12 108.5(3) . . ? C4 C5 C12 108.1(4) . . ? C13 C5 C12 108.1(4) . . ? C8 C9 N2 105.8(4) . . ? C8 C9 C10 129.5(4) . . ? N2 C9 C10 124.4(4) . . ? C2 C1 N1 106.7(4) . . ? C2 C1 C10 127.6(4) . 9_665 ? N1 C1 C10 125.2(4) . 9_665 ? C4 C3 C2 109.2(4) . . ? C1 C2 C3 108.3(4) . . ? O1 C11 C15 121.6(5) . . ? O1 C11 C10 120.7(5) . . ? C15 C11 C10 117.7(4) . . ? C9 C8 C7 108.5(4) . . ? C6 C7 C8 108.4(4) . . ? C9 C10 C1 114.1(3) . 9_665 ? C9 C10 C11 106.8(4) . . ? C1 C10 C11 108.8(4) 9_665 . ? C9 C10 C14 108.3(4) . . ? C1 C10 C14 110.3(4) 9_665 . ? C11 C10 C14 108.3(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.459 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.054 data_1 #TrackingRef '- pkp-cif.cif' _database_code_depnum_ccdc_archive 'CCDC 804422' #TrackingRef '- TransPbca.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H36 N4 O2' _chemical_formula_weight 484.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.3085(18) _cell_length_b 19.412(3) _cell_length_c 23.713(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5205.4(14) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1268 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 15.80 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2080 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9784 _exptl_absorpt_correction_T_max 0.9891 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany The values quoted are generated by SHELX based on crystal size and the corrections are not significant for small crystals composed of light atoms. ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 49734 _diffrn_reflns_av_R_equivalents 0.5031 _diffrn_reflns_av_sigmaI/netI 0.2688 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 26.09 _reflns_number_total 5141 _reflns_number_gt 1572 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0488P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5141 _refine_ls_number_parameters 349 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2978 _refine_ls_R_factor_gt 0.0887 _refine_ls_wR_factor_ref 0.1924 _refine_ls_wR_factor_gt 0.1303 _refine_ls_goodness_of_fit_ref 0.945 _refine_ls_restrained_S_all 0.945 _refine_ls_shift/su_max 1.195 _refine_ls_shift/su_mean 0.003 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 N4 N 0.6056(4) 1.0317(2) 0.6181(2) 0.0391(12) Uani 1 1 d . . . N1 N 0.4088(5) 0.8290(2) 0.64035(19) 0.0361(13) Uani 1 1 d . . . N2 N 0.6225(5) 0.8813(3) 0.5613(2) 0.0419(14) Uani 1 1 d . . . N3 N 0.3766(4) 0.9858(2) 0.6839(2) 0.0386(12) Uani 1 1 d . . . O2 O 0.6321(4) 1.0232(2) 0.44526(16) 0.0625(13) Uani 1 1 d . . . C11 C 0.6411(5) 1.0416(3) 0.5631(2) 0.0406(15) Uani 1 1 d . . . C9 C 0.7235(5) 0.9212(3) 0.5598(2) 0.0377(15) Uani 1 1 d . . . C16 C 0.4298(5) 1.0338(3) 0.7178(2) 0.0379(14) Uani 1 1 d . . . O1 O 0.1088(4) 0.8373(2) 0.76219(18) 0.0814(15) Uani 1 1 d . . . C12 C 0.5998(5) 1.1046(3) 0.5472(2) 0.0519(17) Uani 1 1 d . . . H12 H 0.6107 1.1252 0.5122 0.062 Uiso 1 1 calc R . . C4 C 0.4331(5) 0.7873(2) 0.5949(2) 0.0353(14) Uani 1 1 d . . . C17 C 0.3994(5) 1.0187(3) 0.7715(2) 0.0475(16) Uani 1 1 d . . . H17 H 0.4216 1.0435 0.8034 0.057 Uiso 1 1 calc R . . C5 C 0.5539(5) 0.7595(3) 0.5821(2) 0.0362(14) Uani 1 1 d . . . C20 C 0.2355(5) 0.8846(3) 0.6913(2) 0.0416(15) Uani 1 1 d . . . C18 C 0.3279(5) 0.9585(3) 0.7711(2) 0.0437(16) Uani 1 1 d . . . H18 H 0.2967 0.9362 0.8025 0.052 Uiso 1 1 calc R . . C3 C 0.3260(6) 0.7761(3) 0.5698(2) 0.0477(17) Uani 1 1 d . . . H3 H 0.3133 0.7493 0.5379 0.057 Uiso 1 1 calc R . . C1 C 0.2909(5) 0.8441(3) 0.6436(2) 0.0374(14) Uani 1 1 d . . . C6 C 0.6469(5) 0.8161(3) 0.5807(2) 0.0376(15) Uani 1 1 d . . . C15 C 0.5000(5) 1.0953(3) 0.6965(2) 0.0422(15) Uani 1 1 d . . . C29 C 0.2050(6) 0.8359(3) 0.7395(3) 0.0553(18) Uani 1 1 d . . . C8 C 0.8115(5) 0.8795(3) 0.5785(2) 0.0502(17) Uani 1 1 d . . . H8 H 0.8905 0.8922 0.5823 0.060 Uiso 1 1 calc R . . C22 C 0.5514(5) 0.7235(3) 0.5242(2) 0.0559(18) Uani 1 1 d . . . H22A H 0.4971 0.6856 0.5254 0.084 Uiso 1 1 calc R . . H22B H 0.6290 0.7069 0.5152 0.084 Uiso 1 1 calc R . . H22C H 0.5264 0.7558 0.4959 0.084 Uiso 1 1 calc R . . C26 C 0.6085(5) 1.1044(3) 0.7354(2) 0.0639(19) Uani 1 1 d . . . H26A H 0.6559 1.0634 0.7344 0.096 Uiso 1 1 calc R . . H26B H 0.5824 1.1126 0.7733 0.096 Uiso 1 1 calc R . . H26C H 0.6547 1.1428 0.7226 0.096 Uiso 1 1 calc R . . C28 C 0.1192(5) 0.9179(3) 0.6697(2) 0.0612(19) Uani 1 1 d . . . H28A H 0.1359 0.9457 0.6371 0.092 Uiso 1 1 calc R . . H28B H 0.0858 0.9462 0.6988 0.092 Uiso 1 1 calc R . . H28C H 0.0640 0.8823 0.6597 0.092 Uiso 1 1 calc R . . C23 C 0.6995(6) 0.9849(3) 0.4705(3) 0.0488(17) Uani 1 1 d . . . C7 C 0.7642(5) 0.8138(3) 0.5914(2) 0.0485(17) Uani 1 1 d . . . H7 H 0.8062 0.7760 0.6047 0.058 Uiso 1 1 calc R . . C19 C 0.3135(5) 0.9394(3) 0.7165(2) 0.0371(15) Uani 1 1 d . . . C2 C 0.2380(5) 0.8117(3) 0.6002(2) 0.0487(17) Uani 1 1 d . . . H2 H 0.1577 0.8127 0.5918 0.058 Uiso 1 1 calc R . . C21 C 0.5884(5) 0.7060(3) 0.6271(2) 0.0570(18) Uani 1 1 d . . . H21A H 0.5889 0.7275 0.6636 0.085 Uiso 1 1 calc R . . H21B H 0.6656 0.6881 0.6189 0.085 Uiso 1 1 calc R . . H21C H 0.5320 0.6690 0.6269 0.085 Uiso 1 1 calc R . . C13 C 0.5376(5) 1.1330(3) 0.5931(3) 0.0556(18) Uani 1 1 d . . . H13 H 0.5001 1.1757 0.5935 0.067 Uiso 1 1 calc R . . C14 C 0.5418(5) 1.0875(3) 0.6365(2) 0.0398(15) Uani 1 1 d . . . C25 C 0.8516(5) 1.0227(3) 0.5383(3) 0.067(2) Uani 1 1 d . . . H25A H 0.8545 1.0660 0.5187 0.100 Uiso 1 1 calc R . . H25B H 0.9062 0.9912 0.5211 0.100 Uiso 1 1 calc R . . H25C H 0.8728 1.0295 0.5771 0.100 Uiso 1 1 calc R . . C30 C 0.2988(5) 0.7864(3) 0.7574(2) 0.0601(18) Uani 1 1 d . . . H30A H 0.2754 0.7644 0.7918 0.090 Uiso 1 1 calc R . . H30B H 0.3716 0.8108 0.7632 0.090 Uiso 1 1 calc R . . H30C H 0.3096 0.7522 0.7286 0.090 Uiso 1 1 calc R . . C10 C 0.7236(5) 0.9925(3) 0.5347(2) 0.0403(15) Uani 1 1 d . . . C24 C 0.7640(6) 0.9288(3) 0.4395(2) 0.084(2) Uani 1 1 d . . . H24A H 0.7213 0.8863 0.4432 0.126 Uiso 1 1 calc R . . H24B H 0.8418 0.9235 0.4551 0.126 Uiso 1 1 calc R . . H24C H 0.7701 0.9408 0.4003 0.126 Uiso 1 1 calc R . . C27 C 0.4218(5) 1.1597(3) 0.7013(2) 0.066(2) Uani 1 1 d . . . H27A H 0.4671 1.1997 0.6914 0.100 Uiso 1 1 calc R . . H27B H 0.3939 1.1642 0.7394 0.100 Uiso 1 1 calc R . . H27C H 0.3555 1.1555 0.6763 0.100 Uiso 1 1 calc R . . H1A H 0.461(3) 0.8408(19) 0.6657(16) 0.009(14) Uiso 1 1 d . . . H3A H 0.379(4) 0.984(2) 0.6452(19) 0.043(16) Uiso 1 1 d . . . H2A H 0.561(3) 0.893(2) 0.5536(17) 0.000(14) Uiso 1 1 d . . . H4A H 0.625(5) 0.991(3) 0.642(3) 0.13(3) 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 N4 0.048(3) 0.027(3) 0.042(3) 0.002(3) 0.005(3) 0.005(3) N1 0.041(4) 0.041(3) 0.027(3) -0.005(2) -0.005(3) -0.004(3) N2 0.029(4) 0.047(4) 0.051(3) 0.002(3) -0.010(3) 0.006(3) N3 0.046(3) 0.045(3) 0.024(3) -0.001(3) 0.001(3) -0.004(3) O2 0.079(3) 0.056(3) 0.053(3) 0.000(2) -0.001(3) -0.003(3) C11 0.041(4) 0.034(4) 0.047(4) -0.001(3) 0.010(3) -0.001(3) C9 0.035(4) 0.037(4) 0.041(4) -0.010(3) 0.009(3) -0.006(3) C16 0.035(4) 0.039(4) 0.040(4) -0.005(3) 0.002(3) 0.007(3) O1 0.055(3) 0.098(4) 0.091(4) 0.012(3) 0.033(3) -0.008(3) C12 0.056(5) 0.050(4) 0.050(4) 0.005(3) 0.006(4) -0.004(4) C4 0.049(4) 0.025(3) 0.032(4) -0.003(3) 0.011(3) -0.008(3) C17 0.054(4) 0.051(4) 0.037(4) -0.017(3) -0.001(3) 0.001(3) C5 0.049(4) 0.030(3) 0.029(3) -0.002(3) 0.005(3) -0.002(3) C20 0.043(4) 0.039(4) 0.042(4) 0.004(3) 0.010(3) -0.005(3) C18 0.044(4) 0.050(4) 0.037(4) 0.000(3) 0.009(3) 0.005(3) C3 0.051(4) 0.053(4) 0.038(4) -0.014(3) -0.001(4) -0.007(3) C1 0.029(4) 0.039(4) 0.045(4) -0.003(3) 0.002(3) -0.003(3) C6 0.042(4) 0.034(4) 0.037(4) 0.001(3) 0.001(3) 0.008(3) C15 0.051(4) 0.029(3) 0.046(4) -0.008(3) 0.006(3) 0.006(3) C29 0.058(5) 0.043(4) 0.065(5) -0.002(4) 0.015(4) -0.011(4) C8 0.035(4) 0.062(5) 0.053(4) 0.005(4) -0.007(3) -0.001(4) C22 0.068(5) 0.051(4) 0.049(4) -0.013(3) 0.007(4) 0.005(3) C26 0.058(5) 0.071(4) 0.063(4) -0.013(4) 0.001(4) -0.017(4) C28 0.048(4) 0.064(4) 0.071(5) -0.018(4) -0.003(4) 0.015(4) C23 0.049(4) 0.040(4) 0.057(5) 0.015(4) 0.011(4) -0.003(3) C7 0.050(5) 0.047(4) 0.049(4) 0.015(3) 0.002(3) 0.014(3) C19 0.031(4) 0.042(4) 0.039(4) 0.002(3) 0.001(3) 0.002(3) C2 0.052(4) 0.051(4) 0.043(4) -0.009(3) -0.008(3) -0.009(3) C21 0.068(5) 0.040(4) 0.063(5) 0.014(3) 0.006(4) 0.001(3) C13 0.064(5) 0.043(4) 0.059(5) 0.000(4) 0.002(4) 0.004(3) C14 0.044(4) 0.032(4) 0.043(4) 0.002(3) 0.006(3) -0.002(3) C25 0.043(4) 0.059(4) 0.099(5) -0.014(4) 0.013(4) -0.009(4) C30 0.074(5) 0.053(4) 0.053(4) 0.011(3) 0.012(4) 0.007(4) C10 0.044(4) 0.037(4) 0.040(4) 0.000(3) -0.003(3) -0.010(3) C24 0.111(7) 0.079(5) 0.062(5) -0.013(4) 0.016(5) 0.028(5) C27 0.088(5) 0.039(4) 0.072(5) -0.001(3) 0.019(4) 0.006(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N4 C14 1.372(6) . ? N4 C11 1.380(6) . ? N4 H4A 0.99(6) . ? N1 C1 1.368(6) . ? N1 C4 1.375(6) . ? N1 H1A 0.87(4) . ? N2 C6 1.374(6) . ? N2 C9 1.381(6) . ? N2 H2A 0.75(4) . ? N3 C16 1.369(6) . ? N3 C19 1.385(6) . ? N3 H3A 0.92(4) . ? O2 C23 1.222(6) . ? C11 C12 1.362(6) . ? C11 C10 1.493(7) . ? C9 C8 1.357(7) . ? C9 C10 1.507(7) . ? C16 C17 1.352(6) . ? C16 C15 1.520(7) . ? O1 C29 1.215(6) . ? C12 C13 1.407(7) . ? C12 H12 0.9300 . ? C4 C3 1.367(7) . ? C4 C5 1.501(7) . ? C17 C18 1.421(7) . ? C17 H17 0.9300 . ? C5 C6 1.521(7) . ? C5 C21 1.540(6) . ? C5 C22 1.541(6) . ? C20 C19 1.507(7) . ? C20 C1 1.513(7) . ? C20 C29 1.521(7) . ? C20 C28 1.553(7) . ? C18 C19 1.355(6) . ? C18 H18 0.9300 . ? C3 C2 1.411(7) . ? C3 H3 0.9300 . ? C1 C2 1.346(6) . ? C6 C7 1.351(7) . ? C15 C14 1.506(7) . ? C15 C27 1.536(6) . ? C15 C26 1.545(7) . ? C29 C30 1.492(8) . ? C8 C7 1.417(7) . ? C8 H8 0.9300 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C23 C24 1.504(7) . ? C23 C10 1.554(7) . ? C7 H7 0.9300 . ? C2 H2 0.9300 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C13 C14 1.358(6) . ? C13 H13 0.9300 . ? C25 C10 1.565(6) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 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 C14 N4 C11 110.1(5) . . ? C14 N4 H4A 124(4) . . ? C11 N4 H4A 126(4) . . ? C1 N1 C4 111.4(5) . . ? C1 N1 H1A 124(3) . . ? C4 N1 H1A 124(3) . . ? C6 N2 C9 111.0(5) . . ? C6 N2 H2A 123(3) . . ? C9 N2 H2A 126(3) . . ? C16 N3 C19 109.9(5) . . ? C16 N3 H3A 127(3) . . ? C19 N3 H3A 123(3) . . ? C12 C11 N4 106.6(5) . . ? C12 C11 C10 131.6(6) . . ? N4 C11 C10 121.3(5) . . ? C8 C9 N2 105.3(5) . . ? C8 C9 C10 132.5(6) . . ? N2 C9 C10 121.7(5) . . ? C17 C16 N3 107.1(5) . . ? C17 C16 C15 128.0(6) . . ? N3 C16 C15 124.6(5) . . ? C11 C12 C13 108.1(5) . . ? C11 C12 H12 126.0 . . ? C13 C12 H12 126.0 . . ? C3 C4 N1 105.0(5) . . ? C3 C4 C5 131.3(5) . . ? N1 C4 C5 123.6(5) . . ? C16 C17 C18 108.4(5) . . ? C16 C17 H17 125.8 . . ? C18 C17 H17 125.8 . . ? C4 C5 C6 111.9(4) . . ? C4 C5 C21 109.4(4) . . ? C6 C5 C21 109.1(5) . . ? C4 C5 C22 109.1(5) . . ? C6 C5 C22 108.7(4) . . ? C21 C5 C22 108.5(4) . . ? C19 C20 C1 114.9(5) . . ? C19 C20 C29 106.0(5) . . ? C1 C20 C29 109.4(4) . . ? C19 C20 C28 109.4(4) . . ? C1 C20 C28 108.6(5) . . ? C29 C20 C28 108.4(5) . . ? C19 C18 C17 107.5(5) . . ? C19 C18 H18 126.3 . . ? C17 C18 H18 126.3 . . ? C4 C3 C2 108.9(5) . . ? C4 C3 H3 125.6 . . ? C2 C3 H3 125.6 . . ? C2 C1 N1 106.9(5) . . ? C2 C1 C20 129.0(6) . . ? N1 C1 C20 123.9(5) . . ? C7 C6 N2 106.8(5) . . ? C7 C6 C5 130.6(5) . . ? N2 C6 C5 122.2(5) . . ? C14 C15 C16 113.5(5) . . ? C14 C15 C27 109.4(5) . . ? C16 C15 C27 108.3(5) . . ? C14 C15 C26 108.9(5) . . ? C16 C15 C26 107.9(4) . . ? C27 C15 C26 108.6(5) . . ? O1 C29 C30 121.7(6) . . ? O1 C29 C20 121.4(6) . . ? C30 C29 C20 116.9(6) . . ? C9 C8 C7 109.2(5) . . ? C9 C8 H8 125.4 . . ? C7 C8 H8 125.4 . . ? C5 C22 H22A 109.5 . . ? C5 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C5 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C15 C26 H26A 109.5 . . ? C15 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C15 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C20 C28 H28A 109.5 . . ? C20 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C20 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O2 C23 C24 120.2(6) . . ? O2 C23 C10 122.1(6) . . ? C24 C23 C10 117.6(5) . . ? C6 C7 C8 107.6(5) . . ? C6 C7 H7 126.2 . . ? C8 C7 H7 126.2 . . ? C18 C19 N3 107.1(5) . . ? C18 C19 C20 129.9(6) . . ? N3 C19 C20 122.7(5) . . ? C1 C2 C3 107.8(6) . . ? C1 C2 H2 126.1 . . ? C3 C2 H2 126.1 . . ? C5 C21 H21A 109.5 . . ? C5 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C5 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C14 C13 C12 108.3(5) . . ? C14 C13 H13 125.8 . . ? C12 C13 H13 125.8 . . ? C13 C14 N4 106.9(5) . . ? C13 C14 C15 129.8(5) . . ? N4 C14 C15 123.0(5) . . ? C10 C25 H25A 109.5 . . ? C10 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C10 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C11 C10 C9 114.1(5) . . ? C11 C10 C23 113.1(5) . . ? C9 C10 C23 107.4(4) . . ? C11 C10 C25 108.3(4) . . ? C9 C10 C25 108.9(5) . . ? C23 C10 C25 104.5(5) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C15 C27 H27A 109.5 . . ? C15 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C15 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.09 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.220 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.052 data_5 #TrackingRef '- pkp-cif.cif' _database_code_depnum_ccdc_archive 'CCDC 804966' #TrackingRef 'pkp65_s.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H14 N2 O' _chemical_formula_sum 'C12 H14 N2 O' _chemical_formula_weight 202.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.0771(7) _cell_length_b 19.1132(19) _cell_length_c 8.2747(8) _cell_angle_alpha 90.00 _cell_angle_beta 103.131(2) _cell_angle_gamma 90.00 _cell_volume 1090.02(19) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5215 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 25.89 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9386 _exptl_absorpt_correction_T_max 0.9912 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany The values quoted are generated by SHELX based on crystal size and the corrections are not significant for small crystals composed of light atoms. ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10215 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.98 _reflns_number_total 2137 _reflns_number_gt 1825 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0625P)^2^+0.2343P] 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 2137 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0550 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1242 _refine_ls_wR_factor_gt 0.1188 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.25622(18) 0.50813(6) 0.44936(16) 0.0601(4) Uani 1 1 d . . . C4 C 0.2418(2) 0.37437(7) 0.56622(19) 0.0423(4) Uani 1 1 d . . . N2 N 0.0544(2) 0.29897(8) 0.20409(19) 0.0577(4) Uani 1 1 d . . . N1 N 0.0785(2) 0.39496(8) 0.61371(19) 0.0548(4) Uani 1 1 d . . . C3 C 0.3627(2) 0.34554(9) 0.7031(2) 0.0518(4) Uani 1 1 d . . . H3 H 0.4845 0.3264 0.7076 0.062 Uiso 1 1 calc R . . C6 C 0.2975(2) 0.46393(8) 0.35907(19) 0.0455(4) Uani 1 1 d . . . C9 C 0.0855(2) 0.36496(8) 0.26480(18) 0.0418(4) Uani 1 1 d . . . C5 C 0.2677(2) 0.38542(7) 0.39193(18) 0.0401(4) Uani 1 1 d . . . C8 C 0.4462(2) 0.34382(9) 0.3689(2) 0.0508(4) Uani 1 1 d . . . H8A H 0.5613 0.3632 0.4389 0.076 Uiso 1 1 calc R . . H8B H 0.4555 0.3466 0.2551 0.076 Uiso 1 1 calc R . . H8C H 0.4331 0.2958 0.3982 0.076 Uiso 1 1 calc R . . C10 C -0.0747(2) 0.40318(9) 0.1948(2) 0.0537(4) Uani 1 1 d . . . H10 H -0.0937 0.4504 0.2130 0.064 Uiso 1 1 calc R . . C1 C 0.0954(3) 0.38084(9) 0.7771(2) 0.0640(5) Uani 1 1 d . . . H1 H 0.0032 0.3906 0.8381 0.077 Uiso 1 1 calc R . . C11 C -0.2066(2) 0.35842(11) 0.0899(2) 0.0600(5) Uani 1 1 d . . . H11 H -0.3282 0.3706 0.0265 0.072 Uiso 1 1 calc R . . C12 C -0.1240(3) 0.29518(11) 0.0988(2) 0.0661(5) Uani 1 1 d . . . H12 H -0.1789 0.2554 0.0426 0.079 Uiso 1 1 calc R . . C2 C 0.2693(3) 0.35014(10) 0.8357(2) 0.0619(5) Uani 1 1 d . . . H2 H 0.3183 0.3349 0.9438 0.074 Uiso 1 1 calc R . . C7 C 0.3755(3) 0.48339(10) 0.2113(2) 0.0682(5) Uani 1 1 d . . . H7A H 0.3412 0.5309 0.1805 0.102 Uiso 1 1 calc R . . H7B H 0.3211 0.4530 0.1203 0.102 Uiso 1 1 calc R . . H7C H 0.5142 0.4787 0.2383 0.102 Uiso 1 1 calc R . . H1A H -0.018(3) 0.4156(11) 0.556(2) 0.069(6) Uiso 1 1 d . . . H2A H 0.130(3) 0.2638(11) 0.232(2) 0.067(6) 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 0.0640(8) 0.0445(6) 0.0707(8) -0.0063(6) 0.0132(6) 0.0040(5) C4 0.0431(8) 0.0395(7) 0.0430(8) -0.0039(6) 0.0072(6) -0.0013(6) N2 0.0548(9) 0.0456(8) 0.0655(10) -0.0063(7) -0.0018(7) -0.0031(7) N1 0.0552(9) 0.0581(9) 0.0535(9) 0.0010(7) 0.0176(7) 0.0088(7) C3 0.0523(9) 0.0519(9) 0.0468(9) 0.0011(7) 0.0017(7) -0.0044(7) C6 0.0412(8) 0.0445(8) 0.0463(9) -0.0025(7) 0.0010(6) -0.0025(6) C9 0.0397(8) 0.0455(8) 0.0402(8) -0.0017(6) 0.0087(6) -0.0011(6) C5 0.0371(7) 0.0416(8) 0.0401(8) -0.0017(6) 0.0054(6) 0.0010(6) C8 0.0422(8) 0.0551(9) 0.0549(10) -0.0048(7) 0.0104(7) 0.0035(7) C10 0.0451(9) 0.0578(10) 0.0549(10) -0.0017(7) 0.0044(7) 0.0042(7) C1 0.0834(14) 0.0621(11) 0.0548(11) -0.0085(8) 0.0329(10) -0.0067(10) C11 0.0402(9) 0.0865(14) 0.0493(10) 0.0035(8) 0.0016(7) -0.0056(8) C12 0.0593(11) 0.0678(12) 0.0630(11) -0.0095(9) -0.0031(9) -0.0188(9) C2 0.0822(13) 0.0608(11) 0.0400(9) -0.0006(7) 0.0083(8) -0.0143(10) C7 0.0907(14) 0.0579(11) 0.0566(11) 0.0034(8) 0.0178(10) -0.0169(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 O1 C6 1.2068(19) . ? C4 N1 1.361(2) . ? C4 C3 1.371(2) . ? C4 C5 1.509(2) . ? N2 C9 1.357(2) . ? N2 C12 1.363(2) . ? N2 H2A 0.86(2) . ? N1 C1 1.357(2) . ? N1 H1A 0.84(2) . ? C3 C2 1.406(3) . ? C3 H3 0.9300 . ? C6 C7 1.499(2) . ? C6 C5 1.548(2) . ? C9 C10 1.362(2) . ? C9 C5 1.5186(19) . ? C5 C8 1.541(2) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C10 C11 1.410(2) . ? C10 H10 0.9300 . ? C1 C2 1.350(3) . ? C1 H1 0.9300 . ? C11 C12 1.337(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C2 H2 0.9300 . ? 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 N1 C4 C3 106.80(15) . . ? N1 C4 C5 122.07(13) . . ? C3 C4 C5 131.12(14) . . ? C9 N2 C12 109.57(16) . . ? C9 N2 H2A 126.1(13) . . ? C12 N2 H2A 124.1(13) . . ? C1 N1 C4 110.00(16) . . ? C1 N1 H1A 122.5(14) . . ? C4 N1 H1A 127.5(14) . . ? C4 C3 C2 107.70(16) . . ? C4 C3 H3 126.2 . . ? C2 C3 H3 126.2 . . ? O1 C6 C7 121.15(15) . . ? O1 C6 C5 120.54(15) . . ? C7 C6 C5 118.30(14) . . ? N2 C9 C10 106.96(14) . . ? N2 C9 C5 122.46(13) . . ? C10 C9 C5 130.54(14) . . ? C4 C5 C9 110.95(12) . . ? C4 C5 C8 109.09(12) . . ? C9 C5 C8 111.86(12) . . ? C4 C5 C6 110.76(12) . . ? C9 C5 C6 104.84(11) . . ? C8 C5 C6 109.28(12) . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C9 C10 C11 107.86(16) . . ? C9 C10 H10 126.1 . . ? C11 C10 H10 126.1 . . ? C2 C1 N1 108.11(16) . . ? C2 C1 H1 125.9 . . ? N1 C1 H1 125.9 . . ? C12 C11 C10 107.14(15) . . ? C12 C11 H11 126.4 . . ? C10 C11 H11 126.4 . . ? C11 C12 N2 108.47(16) . . ? C11 C12 H12 125.8 . . ? N2 C12 H12 125.8 . . ? C1 C2 C3 107.39(16) . . ? C1 C2 H2 126.3 . . ? C3 C2 H2 126.3 . . ? 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 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.193 _refine_diff_density_min -0.140 _refine_diff_density_rms 0.033