# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1475 loop_ _publ_author_name 'Hawker, Craig' 'Wolffs, Martin' 'Campos, Luis' 'Delaney, Kris' 'Treat, Nic' 'Moon, Bongjin' 'Kade, Matt' _publ_contact_author_name 'Hawker, Craig' _publ_contact_author_email hawker@mrl.ucsb.edu _publ_section_title ; Low temperature ketene formation in polymer systems through molecular engineering ; # Attachment '- Dibenzyl.CIF' data_f1102091 _database_code_depnum_ccdc_archive 'CCDC 850274' #TrackingRef '- Dibenzyl.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H22 O4' _chemical_formula_weight 350.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.534(2) _cell_length_b 19.600(5) _cell_length_c 10.977(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.365(3) _cell_angle_gamma 90.00 _cell_volume 1923.0(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.210 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.309 _exptl_absorpt_correction_T_max 0.432 _exptl_absorpt_process_details 'psi scan' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13767 _diffrn_reflns_av_R_equivalents 0.1455 _diffrn_reflns_av_sigmaI/netI 0.1843 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.70 _reflns_number_total 3575 _reflns_number_gt 962 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0563P)^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 SHELXL _refine_ls_extinction_coef 0.0085(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3575 _refine_ls_number_parameters 238 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.2384 _refine_ls_R_factor_gt 0.0512 _refine_ls_wR_factor_ref 0.1584 _refine_ls_wR_factor_gt 0.1108 _refine_ls_goodness_of_fit_ref 0.797 _refine_ls_restrained_S_all 0.813 _refine_ls_shift/su_max 0.003 _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 -0.2641(7) 0.2722(2) 0.4613(5) 0.0964(15) Uani 1 1 d . . . H1 H -0.2666 0.3058 0.4007 0.116 Uiso 1 1 calc R . . C2 C -0.3953(7) 0.2552(3) 0.4812(6) 0.1167(18) Uani 1 1 d . . . H2 H -0.4834 0.2784 0.4366 0.140 Uiso 1 1 calc R . . C3 C -0.3952(7) 0.2042(3) 0.5667(6) 0.1101(18) Uani 1 1 d . . . H3 H -0.4833 0.1919 0.5794 0.132 Uiso 1 1 calc R . . C4 C -0.2645(7) 0.1719(2) 0.6328(5) 0.0955(15) Uani 1 1 d . . . H4 H -0.2642 0.1374 0.6911 0.115 Uiso 1 1 calc R . . C5 C -0.1319(6) 0.1892(2) 0.6154(4) 0.0849(14) Uani 1 1 d . . . H5 H -0.0440 0.1663 0.6615 0.102 Uiso 1 1 calc R . . C6 C -0.1303(6) 0.2411(2) 0.5284(5) 0.0756(13) Uani 1 1 d . . . C7 C 0.0123(5) 0.2596(2) 0.5095(4) 0.0865(14) Uani 1 1 d . . . H7A H -0.0085 0.2666 0.4174 0.104 Uiso 1 1 calc R . . H7B H 0.0804 0.2213 0.5365 0.104 Uiso 1 1 calc R . . C8 C 0.0930(5) 0.3244(2) 0.5839(4) 0.0659(12) Uani 1 1 d . . . C9 C 0.1300(5) 0.3128(2) 0.7289(5) 0.0700(13) Uani 1 1 d . . . C10 C -0.0039(5) 0.3862(2) 0.5316(6) 0.0751(13) Uani 1 1 d . . . C11 C -0.0186(6) 0.4109(2) 0.7425(5) 0.0822(14) Uani 1 1 d . . . C12 C 0.0588(7) 0.4745(3) 0.8074(5) 0.154(2) Uani 1 1 d . . . H12A H 0.0725 0.4729 0.8982 0.230 Uiso 1 1 calc R . . H12B H -0.0008 0.5135 0.7684 0.230 Uiso 1 1 calc R . . H12C H 0.1546 0.4779 0.7971 0.230 Uiso 1 1 calc R . . C13 C -0.1602(6) 0.3949(3) 0.7621(6) 0.156(3) Uani 1 1 d . . . H13A H -0.2010 0.3534 0.7174 0.234 Uiso 1 1 calc R . . H13B H -0.2301 0.4315 0.7285 0.234 Uiso 1 1 calc R . . H13C H -0.1420 0.3895 0.8533 0.234 Uiso 1 1 calc R . . C14 C 0.2405(5) 0.3329(2) 0.5581(4) 0.0878(14) Uani 1 1 d . . . H14A H 0.3004 0.2921 0.5874 0.105 Uiso 1 1 calc R . . H14B H 0.2179 0.3367 0.4651 0.105 Uiso 1 1 calc R . . C15 C 0.3324(6) 0.3941(2) 0.6236(6) 0.0771(13) Uani 1 1 d . . . C16 C 0.4309(7) 0.3899(3) 0.7494(7) 0.1056(17) Uani 1 1 d . . . H16 H 0.4416 0.3485 0.7931 0.127 Uiso 1 1 calc R . . C17 C 0.5137(6) 0.4448(4) 0.8124(6) 0.1140(18) Uani 1 1 d . . . H17 H 0.5775 0.4402 0.8981 0.137 Uiso 1 1 calc R . . C18 C 0.5035(7) 0.5062(4) 0.7507(8) 0.111(2) Uani 1 1 d D . . C19 C 0.4036(7) 0.5120(3) 0.6249(7) 0.1120(19) Uani 1 1 d . . . H19 H 0.3927 0.5536 0.5816 0.134 Uiso 1 1 calc R . . C20 C 0.3193(6) 0.4561(3) 0.5631(5) 0.0998(16) Uani 1 1 d . . . H20 H 0.2524 0.4609 0.4786 0.120 Uiso 1 1 calc R . . C21 C 0.6007(8) 0.5625(4) 0.8266(8) 0.171(3) Uani 1 1 d D . . H21 H 0.6280 0.5609 0.9166 0.205 Uiso 1 1 calc R . . C22 C 0.6449(9) 0.6077(4) 0.7833(10) 0.231(5) Uani 1 1 d D . . H22A H 0.6203 0.6113 0.6938 0.278 Uiso 1 1 calc R . . H22B H 0.7051 0.6406 0.8378 0.278 Uiso 1 1 calc R . . O1 O 0.2044(3) 0.26573(15) 0.7848(3) 0.0941(11) Uani 1 1 d . . . O2 O 0.0813(4) 0.35645(16) 0.7951(3) 0.1005(11) Uani 1 1 d . . . O3 O -0.0392(4) 0.40221(14) 0.4192(4) 0.1003(12) Uani 1 1 d . . . O4 O -0.0515(4) 0.42272(14) 0.6086(4) 0.1001(11) 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 0.084(4) 0.098(4) 0.098(4) 0.011(3) 0.021(4) -0.013(4) C2 0.085(5) 0.116(5) 0.132(5) 0.014(4) 0.017(4) -0.015(4) C3 0.089(5) 0.126(5) 0.107(5) -0.004(4) 0.024(4) -0.023(4) C4 0.102(4) 0.097(4) 0.080(4) 0.002(3) 0.024(4) -0.035(4) C5 0.094(4) 0.066(3) 0.092(4) -0.007(3) 0.028(3) -0.019(3) C6 0.089(4) 0.065(3) 0.074(3) -0.012(3) 0.029(3) -0.012(3) C7 0.100(4) 0.077(3) 0.097(4) -0.009(3) 0.053(3) -0.005(3) C8 0.072(3) 0.055(3) 0.082(4) 0.000(3) 0.041(3) 0.000(2) C9 0.054(3) 0.059(3) 0.100(4) 0.007(3) 0.030(3) 0.005(2) C10 0.076(4) 0.065(3) 0.091(4) 0.004(3) 0.037(4) -0.007(3) C11 0.104(4) 0.073(3) 0.078(4) 0.006(3) 0.042(3) 0.022(3) C12 0.214(7) 0.099(4) 0.117(5) -0.003(4) 0.019(5) -0.003(4) C13 0.112(5) 0.210(6) 0.175(6) 0.075(5) 0.087(5) 0.056(4) C14 0.085(3) 0.084(3) 0.109(4) -0.002(3) 0.051(3) -0.005(3) C15 0.065(4) 0.074(4) 0.097(4) 0.007(3) 0.035(3) 0.006(3) C16 0.063(4) 0.105(5) 0.147(6) 0.024(4) 0.035(4) -0.003(4) C17 0.063(4) 0.135(5) 0.139(6) 0.013(5) 0.030(4) -0.003(4) C18 0.064(4) 0.096(5) 0.181(7) -0.026(5) 0.051(5) -0.008(4) C19 0.092(5) 0.078(4) 0.163(6) 0.007(4) 0.041(5) -0.007(4) C20 0.090(4) 0.085(4) 0.123(4) 0.017(4) 0.036(4) -0.002(4) C21 0.125(6) 0.118(6) 0.319(10) -0.016(7) 0.139(7) -0.003(5) C22 0.165(7) 0.154(8) 0.414(15) -0.083(8) 0.151(9) -0.037(6) O1 0.086(2) 0.081(2) 0.117(3) 0.0304(19) 0.037(2) 0.0266(19) O2 0.128(3) 0.098(2) 0.084(2) 0.0213(19) 0.048(2) 0.054(2) O3 0.124(3) 0.091(2) 0.083(2) 0.016(2) 0.032(2) -0.0073(19) O4 0.128(3) 0.089(2) 0.089(3) 0.0138(19) 0.046(2) 0.043(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 C6 1.375(5) . ? C1 C2 1.382(6) . ? C1 H1 0.9300 . ? C2 C3 1.372(6) . ? C2 H2 0.9300 . ? C3 C4 1.361(6) . ? C3 H3 0.9300 . ? C4 C5 1.385(6) . ? C4 H4 0.9300 . ? C5 C6 1.399(5) . ? C5 H5 0.9300 . ? C6 C7 1.489(5) . ? C7 C8 1.559(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C10 1.511(5) . ? C8 C9 1.523(5) . ? C8 C14 1.537(5) . ? C9 O1 1.195(4) . ? C9 O2 1.309(4) . ? C10 O3 1.202(5) . ? C10 O4 1.304(5) . ? C11 O4 1.411(5) . ? C11 O2 1.413(5) . ? C11 C13 1.473(6) . ? C11 C12 1.497(6) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.512(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C20 1.370(5) . ? C15 C16 1.376(6) . ? C16 C17 1.370(7) . ? C16 H16 0.9300 . ? C17 C18 1.368(7) . ? C17 H17 0.9300 . ? C18 C19 1.383(7) . ? C18 C21 1.494(7) . ? C19 C20 1.388(6) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.153(6) . ? C21 H21 0.9300 . ? C22 H22A 0.9300 . ? C22 H22B 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 C6 C1 C2 122.0(5) . . ? C6 C1 H1 119.0 . . ? C2 C1 H1 119.0 . . ? C3 C2 C1 119.9(6) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C4 C3 C2 119.1(5) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 121.5(5) . . ? C3 C4 H4 119.2 . . ? C5 C4 H4 119.2 . . ? C4 C5 C6 120.0(5) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C1 C6 C5 117.4(4) . . ? C1 C6 C7 122.6(5) . . ? C5 C6 C7 120.0(5) . . ? C6 C7 C8 115.7(3) . . ? C6 C7 H7A 108.3 . . ? C8 C7 H7A 108.3 . . ? C6 C7 H7B 108.3 . . ? C8 C7 H7B 108.3 . . ? H7A C7 H7B 107.4 . . ? C10 C8 C9 113.9(4) . . ? C10 C8 C14 108.7(3) . . ? C9 C8 C14 108.4(4) . . ? C10 C8 C7 109.2(4) . . ? C9 C8 C7 108.5(3) . . ? C14 C8 C7 108.0(3) . . ? O1 C9 O2 118.8(5) . . ? O1 C9 C8 122.2(4) . . ? O2 C9 C8 119.0(4) . . ? O3 C10 O4 119.0(5) . . ? O3 C10 C8 121.0(5) . . ? O4 C10 C8 119.9(5) . . ? O4 C11 O2 115.1(3) . . ? O4 C11 C13 107.7(5) . . ? O2 C11 C13 107.5(4) . . ? O4 C11 C12 104.6(4) . . ? O2 C11 C12 106.5(4) . . ? C13 C11 C12 115.6(4) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C8 114.5(3) . . ? C15 C14 H14A 108.6 . . ? C8 C14 H14A 108.6 . . ? C15 C14 H14B 108.6 . . ? C8 C14 H14B 108.6 . . ? H14A C14 H14B 107.6 . . ? C20 C15 C16 117.0(5) . . ? C20 C15 C14 122.3(6) . . ? C16 C15 C14 120.7(5) . . ? C17 C16 C15 122.1(6) . . ? C17 C16 H16 118.9 . . ? C15 C16 H16 118.9 . . ? C18 C17 C16 120.8(6) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C17 C18 C19 118.2(6) . . ? C17 C18 C21 116.8(8) . . ? C19 C18 C21 125.0(8) . . ? C18 C19 C20 120.2(6) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C15 C20 C19 121.6(5) . . ? C15 C20 H20 119.2 . . ? C19 C20 H20 119.2 . . ? C22 C21 C18 125.6(10) . . ? C22 C21 H21 117.2 . . ? C18 C21 H21 117.2 . . ? C21 C22 H22A 120.0 . . ? C21 C22 H22B 120.0 . . ? H22A C22 H22B 120.0 . . ? C9 O2 C11 125.9(4) . . ? C10 O4 C11 125.7(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 C6 C1 C2 C3 -2.4(8) . . . . ? C1 C2 C3 C4 1.2(8) . . . . ? C2 C3 C4 C5 -0.2(8) . . . . ? C3 C4 C5 C6 0.2(7) . . . . ? C2 C1 C6 C5 2.3(7) . . . . ? C2 C1 C6 C7 -179.0(4) . . . . ? C4 C5 C6 C1 -1.2(6) . . . . ? C4 C5 C6 C7 -179.9(4) . . . . ? C1 C6 C7 C8 81.1(5) . . . . ? C5 C6 C7 C8 -100.2(5) . . . . ? C6 C7 C8 C10 -64.9(5) . . . . ? C6 C7 C8 C9 59.8(5) . . . . ? C6 C7 C8 C14 177.1(4) . . . . ? C10 C8 C9 O1 179.3(4) . . . . ? C14 C8 C9 O1 -59.6(5) . . . . ? C7 C8 C9 O1 57.5(5) . . . . ? C10 C8 C9 O2 -2.1(5) . . . . ? C14 C8 C9 O2 119.1(4) . . . . ? C7 C8 C9 O2 -123.9(4) . . . . ? C9 C8 C10 O3 178.5(4) . . . . ? C14 C8 C10 O3 57.6(6) . . . . ? C7 C8 C10 O3 -60.0(5) . . . . ? C9 C8 C10 O4 -2.1(5) . . . . ? C14 C8 C10 O4 -123.0(4) . . . . ? C7 C8 C10 O4 119.4(4) . . . . ? C10 C8 C14 C15 61.5(5) . . . . ? C9 C8 C14 C15 -62.8(5) . . . . ? C7 C8 C14 C15 179.8(4) . . . . ? C8 C14 C15 C20 -92.2(5) . . . . ? C8 C14 C15 C16 86.0(5) . . . . ? C20 C15 C16 C17 -0.4(7) . . . . ? C14 C15 C16 C17 -178.7(4) . . . . ? C15 C16 C17 C18 -1.3(8) . . . . ? C16 C17 C18 C19 2.3(8) . . . . ? C16 C17 C18 C21 -178.7(5) . . . . ? C17 C18 C19 C20 -1.6(8) . . . . ? C21 C18 C19 C20 179.5(5) . . . . ? C16 C15 C20 C19 1.2(7) . . . . ? C14 C15 C20 C19 179.4(4) . . . . ? C18 C19 C20 C15 -0.2(7) . . . . ? C17 C18 C21 C22 152.8(8) . . . . ? C19 C18 C21 C22 -28.3(11) . . . . ? O1 C9 O2 C11 -173.8(4) . . . . ? C8 C9 O2 C11 7.5(6) . . . . ? O4 C11 O2 C9 -8.3(6) . . . . ? C13 C11 O2 C9 111.8(5) . . . . ? C12 C11 O2 C9 -123.7(5) . . . . ? O3 C10 O4 C11 -179.4(4) . . . . ? C8 C10 O4 C11 1.2(6) . . . . ? O2 C11 O4 C10 3.5(7) . . . . ? C13 C11 O4 C10 -116.4(5) . . . . ? C12 C11 O4 C10 120.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 25.70 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.167 _refine_diff_density_min -0.142 _refine_diff_density_rms 0.029 # Attachment '- Five mem amine.CIF' data_f102509 _database_code_depnum_ccdc_archive 'CCDC 850275' #TrackingRef '- Five mem amine.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H29 N O4' _chemical_formula_weight 371.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.399(3) _cell_length_b 7.8427(14) _cell_length_c 16.851(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.538(3) _cell_angle_gamma 90.00 _cell_volume 2054.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.201 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.283 _exptl_absorpt_correction_T_max 0.395 _exptl_absorpt_process_details 'Psi scan' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15914 _diffrn_reflns_av_R_equivalents 0.0964 _diffrn_reflns_av_sigmaI/netI 0.0921 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 26.42 _reflns_number_total 4134 _reflns_number_gt 1822 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0500P)^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 SHELXL _refine_ls_extinction_coef 0.0352(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4134 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1239 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.1168 _refine_ls_wR_factor_gt 0.0927 _refine_ls_goodness_of_fit_ref 0.844 _refine_ls_restrained_S_all 0.844 _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 0.32920(16) 0.9244(3) 0.37594(15) 0.0705(7) Uani 1 1 d . . . H1A H 0.3658 0.8805 0.4292 0.085 Uiso 1 1 calc R . . H1B H 0.2737 0.8686 0.3630 0.085 Uiso 1 1 calc R . . C2 C 0.31781(17) 1.1130(3) 0.38315(18) 0.0814(8) Uani 1 1 d . . . H2A H 0.2926 1.1353 0.4269 0.098 Uiso 1 1 calc R . . H2B H 0.2788 1.1562 0.3309 0.098 Uiso 1 1 calc R . . C3 C 0.40331(17) 1.2045(3) 0.40321(15) 0.0784(7) Uani 1 1 d . . . H3A H 0.4400 1.1725 0.4587 0.094 Uiso 1 1 calc R . . H3B H 0.3943 1.3268 0.4025 0.094 Uiso 1 1 calc R . . C4 C 0.44615(15) 1.1566(3) 0.33881(16) 0.0723(7) Uani 1 1 d . . . H4A H 0.4133 1.2031 0.2848 0.087 Uiso 1 1 calc R . . H4B H 0.5034 1.2057 0.3546 0.087 Uiso 1 1 calc R . . C5 C 0.45227(14) 0.9649(3) 0.33201(15) 0.0660(6) Uani 1 1 d . . . H5A H 0.4782 0.9375 0.2892 0.079 Uiso 1 1 calc R . . H5B H 0.4890 0.9195 0.3848 0.079 Uiso 1 1 calc R . . C6 C 0.37333(14) 0.7019(3) 0.29932(14) 0.0642(6) Uani 1 1 d . . . H6A H 0.3970 0.6484 0.3537 0.077 Uiso 1 1 calc R . . H6B H 0.4128 0.6810 0.2681 0.077 Uiso 1 1 calc R . . C7 C 0.28713(14) 0.6188(3) 0.25336(13) 0.0624(6) Uani 1 1 d . . . H7A H 0.2489 0.6343 0.2865 0.075 Uiso 1 1 calc R . . H7B H 0.2961 0.4973 0.2495 0.075 Uiso 1 1 calc R . . C8 C 0.24235(12) 0.6881(2) 0.16474(13) 0.0458(5) Uani 1 1 d . . . C9 C 0.30069(13) 0.6657(3) 0.11273(13) 0.0514(6) Uani 1 1 d . . . C10 C 0.21242(13) 0.8681(3) 0.16914(13) 0.0500(5) Uani 1 1 d . . . C11 C 0.28267(15) 0.9644(3) 0.06852(14) 0.0572(6) Uani 1 1 d . . . C12 C 0.22536(17) 0.9958(3) -0.01885(15) 0.0852(8) Uani 1 1 d . . . H12A H 0.2580 0.9848 -0.0569 0.128 Uiso 1 1 calc R . . H12B H 0.2018 1.1087 -0.0228 0.128 Uiso 1 1 calc R . . H12C H 0.1794 0.9139 -0.0330 0.128 Uiso 1 1 calc R . . C13 C 0.35797(17) 1.0834(3) 0.09747(16) 0.0867(8) Uani 1 1 d . . . H13A H 0.3916 1.0552 0.1538 0.130 Uiso 1 1 calc R . . H13B H 0.3377 1.1986 0.0956 0.130 Uiso 1 1 calc R . . H13C H 0.3928 1.0725 0.0615 0.130 Uiso 1 1 calc R . . C14 C 0.15999(14) 0.5779(3) 0.12414(13) 0.0590(6) Uani 1 1 d . . . H14A H 0.1774 0.4596 0.1246 0.071 Uiso 1 1 calc R . . H14B H 0.1232 0.5864 0.1590 0.071 Uiso 1 1 calc R . . C15 C 0.10793(13) 0.6242(3) 0.03619(14) 0.0503(5) Uani 1 1 d . . . C16 C 0.12712(15) 0.5557(3) -0.03159(16) 0.0596(6) Uani 1 1 d . . . H16 H 0.1736 0.4818 -0.0224 0.072 Uiso 1 1 calc R . . C17 C 0.07845(15) 0.5953(3) -0.11241(15) 0.0601(6) Uani 1 1 d . . . H17 H 0.0935 0.5494 -0.1567 0.072 Uiso 1 1 calc R . . C18 C 0.00759(14) 0.7020(3) -0.12920(14) 0.0539(6) Uani 1 1 d . . . C19 C -0.00999(14) 0.7731(3) -0.06164(16) 0.0621(6) Uani 1 1 d . . . H19 H -0.0559 0.8484 -0.0708 0.075 Uiso 1 1 calc R . . C20 C 0.03904(14) 0.7350(3) 0.01908(15) 0.0593(6) Uani 1 1 d . . . H20 H 0.0254 0.7850 0.0633 0.071 Uiso 1 1 calc R . . C21 C -0.05016(16) 0.7365(3) -0.21436(17) 0.0693(7) Uani 1 1 d . . . H21 H -0.0936 0.8157 -0.2189 0.083 Uiso 1 1 calc R . . C22 C -0.0476(2) 0.6709(3) -0.28255(19) 0.0953(9) Uani 1 1 d . . . H22A H -0.0055 0.5909 -0.2819 0.114 Uiso 1 1 calc R . . H22B H -0.0878 0.7028 -0.3330 0.114 Uiso 1 1 calc R . . N N 0.36748(10) 0.8849(2) 0.31088(10) 0.0519(5) Uani 1 1 d . . . O1 O 0.33363(10) 0.53185(19) 0.10697(10) 0.0750(5) Uani 1 1 d . . . O2 O 0.31743(10) 0.79687(19) 0.07147(10) 0.0756(5) Uani 1 1 d . . . O3 O 0.16710(10) 0.90751(19) 0.20957(10) 0.0683(5) Uani 1 1 d . . . O4 O 0.23211(11) 0.98851(17) 0.12231(10) 0.0721(5) 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 0.0795(18) 0.0807(17) 0.0609(16) -0.0045(13) 0.0358(14) -0.0124(13) C2 0.088(2) 0.0812(17) 0.090(2) -0.0223(15) 0.0500(16) -0.0059(15) C3 0.096(2) 0.0737(16) 0.0664(17) -0.0129(13) 0.0266(15) -0.0101(15) C4 0.0668(17) 0.0743(16) 0.0775(18) -0.0089(13) 0.0254(14) -0.0203(13) C5 0.0524(15) 0.0789(16) 0.0633(16) -0.0051(13) 0.0134(12) -0.0019(13) C6 0.0675(16) 0.0593(14) 0.0553(15) 0.0092(11) 0.0045(12) 0.0112(12) C7 0.0737(17) 0.0527(13) 0.0543(15) 0.0076(11) 0.0111(13) -0.0068(12) C8 0.0453(12) 0.0433(11) 0.0489(13) 0.0036(10) 0.0149(10) -0.0016(10) C9 0.0463(13) 0.0465(13) 0.0575(15) -0.0031(11) 0.0110(11) -0.0006(10) C10 0.0422(13) 0.0568(13) 0.0495(14) -0.0003(11) 0.0126(11) -0.0012(10) C11 0.0717(16) 0.0482(13) 0.0570(15) 0.0071(11) 0.0283(13) -0.0004(12) C12 0.097(2) 0.0861(18) 0.0637(18) 0.0050(15) 0.0126(15) -0.0102(16) C13 0.089(2) 0.0866(19) 0.0792(19) -0.0063(15) 0.0198(15) -0.0250(16) C14 0.0565(15) 0.0600(14) 0.0607(15) 0.0012(11) 0.0189(12) -0.0128(11) C15 0.0432(13) 0.0509(12) 0.0558(15) -0.0026(11) 0.0145(11) -0.0129(11) C16 0.0561(15) 0.0548(13) 0.0673(17) -0.0104(12) 0.0187(13) 0.0002(11) C17 0.0658(16) 0.0598(14) 0.0565(16) -0.0124(12) 0.0219(13) -0.0071(12) C18 0.0502(14) 0.0491(12) 0.0592(16) 0.0008(11) 0.0127(12) -0.0074(11) C19 0.0486(14) 0.0643(14) 0.0697(18) -0.0079(13) 0.0135(13) -0.0001(11) C20 0.0480(14) 0.0714(15) 0.0623(17) -0.0132(12) 0.0230(12) -0.0086(12) C21 0.0775(18) 0.0559(14) 0.0736(19) -0.0012(13) 0.0228(15) -0.0038(12) C22 0.121(3) 0.0790(19) 0.077(2) -0.0010(16) 0.0180(18) 0.0150(17) N 0.0482(11) 0.0568(11) 0.0507(11) -0.0012(9) 0.0156(9) -0.0012(9) O1 0.0749(11) 0.0557(10) 0.0980(14) -0.0053(9) 0.0326(10) 0.0148(8) O2 0.1005(13) 0.0582(10) 0.0919(13) 0.0134(9) 0.0642(11) 0.0119(9) O3 0.0601(10) 0.0814(11) 0.0716(11) -0.0068(8) 0.0325(9) 0.0060(8) O4 0.1050(13) 0.0481(9) 0.0803(12) 0.0165(8) 0.0537(11) 0.0180(8) _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 N 1.459(2) . ? C1 C2 1.501(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.514(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.516(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.514(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 N 1.463(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N 1.455(2) . ? C6 C7 1.525(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.539(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.499(3) . ? C8 C10 1.504(3) . ? C8 C14 1.566(3) . ? C9 O1 1.198(2) . ? C9 O2 1.319(2) . ? C10 O3 1.198(2) . ? C10 O4 1.335(2) . ? C11 O4 1.422(2) . ? C11 O2 1.427(2) . ? C11 C12 1.494(3) . ? C11 C13 1.500(3) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.501(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C20 1.381(3) . ? C15 C16 1.386(3) . ? C16 C17 1.377(3) . ? C16 H16 0.9300 . ? C17 C18 1.386(3) . ? C17 H17 0.9300 . ? C18 C19 1.378(3) . ? C18 C21 1.471(3) . ? C19 C20 1.375(3) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.272(3) . ? C21 H21 0.9300 . ? C22 H22A 0.9300 . ? C22 H22B 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 N C1 C2 111.39(18) . . ? N C1 H1A 109.4 . . ? C2 C1 H1A 109.3 . . ? N C1 H1B 109.4 . . ? C2 C1 H1B 109.4 . . ? H1A C1 H1B 108.0 . . ? C1 C2 C3 110.8(2) . . ? C1 C2 H2A 109.5 . . ? C3 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? C2 C3 C4 109.3(2) . . ? C2 C3 H3A 109.8 . . ? C4 C3 H3A 109.8 . . ? C2 C3 H3B 109.8 . . ? C4 C3 H3B 109.8 . . ? H3A C3 H3B 108.3 . . ? C5 C4 C3 110.93(19) . . ? C5 C4 H4A 109.5 . . ? C3 C4 H4A 109.5 . . ? C5 C4 H4B 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 108.0 . . ? N C5 C4 111.33(18) . . ? N C5 H5A 109.4 . . ? C4 C5 H5A 109.4 . . ? N C5 H5B 109.4 . . ? C4 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? N C6 C7 113.53(18) . . ? N C6 H6A 108.9 . . ? C7 C6 H6A 108.9 . . ? N C6 H6B 108.9 . . ? C7 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? C6 C7 C8 114.91(17) . . ? C6 C7 H7A 108.5 . . ? C8 C7 H7A 108.5 . . ? C6 C7 H7B 108.5 . . ? C8 C7 H7B 108.5 . . ? H7A C7 H7B 107.5 . . ? C9 C8 C10 114.72(17) . . ? C9 C8 C7 109.24(17) . . ? C10 C8 C7 110.26(17) . . ? C9 C8 C14 107.55(17) . . ? C10 C8 C14 106.86(16) . . ? C7 C8 C14 107.94(15) . . ? O1 C9 O2 117.8(2) . . ? O1 C9 C8 122.6(2) . . ? O2 C9 C8 119.66(18) . . ? O3 C10 O4 117.65(19) . . ? O3 C10 C8 122.81(19) . . ? O4 C10 C8 119.40(18) . . ? O4 C11 O2 114.04(16) . . ? O4 C11 C12 107.1(2) . . ? O2 C11 C12 107.76(19) . . ? O4 C11 C13 107.25(19) . . ? O2 C11 C13 106.4(2) . . ? C12 C11 C13 114.40(19) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C8 116.00(16) . . ? C15 C14 H14A 108.3 . . ? C8 C14 H14A 108.3 . . ? C15 C14 H14B 108.3 . . ? C8 C14 H14B 108.3 . . ? H14A C14 H14B 107.4 . . ? C20 C15 C16 117.2(2) . . ? C20 C15 C14 122.0(2) . . ? C16 C15 C14 120.8(2) . . ? C17 C16 C15 121.0(2) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C16 C17 C18 121.5(2) . . ? C16 C17 H17 119.2 . . ? C18 C17 H17 119.2 . . ? C19 C18 C17 117.2(2) . . ? C19 C18 C21 119.5(2) . . ? C17 C18 C21 123.2(2) . . ? C20 C19 C18 121.3(2) . . ? C20 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? C19 C20 C15 121.7(2) . . ? C19 C20 H20 119.1 . . ? C15 C20 H20 119.1 . . ? C22 C21 C18 127.6(3) . . ? C22 C21 H21 116.2 . . ? C18 C21 H21 116.2 . . ? C21 C22 H22A 120.0 . . ? C21 C22 H22B 120.0 . . ? H22A C22 H22B 120.0 . . ? C6 N C1 111.87(17) . . ? C6 N C5 110.95(17) . . ? C1 N C5 109.19(17) . . ? C9 O2 C11 126.10(16) . . ? C10 O4 C11 125.63(16) . . ? 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 N C1 C2 C3 -58.9(3) . . . . ? C1 C2 C3 C4 54.1(3) . . . . ? C2 C3 C4 C5 -53.4(3) . . . . ? C3 C4 C5 N 57.3(3) . . . . ? N C6 C7 C8 59.8(3) . . . . ? C6 C7 C8 C9 58.1(2) . . . . ? C6 C7 C8 C10 -68.8(2) . . . . ? C6 C7 C8 C14 174.78(18) . . . . ? C10 C8 C9 O1 175.76(19) . . . . ? C7 C8 C9 O1 51.4(3) . . . . ? C14 C8 C9 O1 -65.5(3) . . . . ? C10 C8 C9 O2 -4.0(3) . . . . ? C7 C8 C9 O2 -128.36(19) . . . . ? C14 C8 C9 O2 114.7(2) . . . . ? C9 C8 C10 O3 -178.4(2) . . . . ? C7 C8 C10 O3 -54.5(3) . . . . ? C14 C8 C10 O3 62.5(3) . . . . ? C9 C8 C10 O4 6.0(3) . . . . ? C7 C8 C10 O4 129.8(2) . . . . ? C14 C8 C10 O4 -113.1(2) . . . . ? C9 C8 C14 C15 -61.2(2) . . . . ? C10 C8 C14 C15 62.4(2) . . . . ? C7 C8 C14 C15 -178.97(18) . . . . ? C8 C14 C15 C20 -93.5(2) . . . . ? C8 C14 C15 C16 87.0(2) . . . . ? C20 C15 C16 C17 -0.8(3) . . . . ? C14 C15 C16 C17 178.71(18) . . . . ? C15 C16 C17 C18 -1.4(3) . . . . ? C16 C17 C18 C19 2.8(3) . . . . ? C16 C17 C18 C21 -174.9(2) . . . . ? C17 C18 C19 C20 -2.2(3) . . . . ? C21 C18 C19 C20 175.60(19) . . . . ? C18 C19 C20 C15 0.1(3) . . . . ? C16 C15 C20 C19 1.5(3) . . . . ? C14 C15 C20 C19 -178.07(19) . . . . ? C19 C18 C21 C22 -173.7(2) . . . . ? C17 C18 C21 C22 3.9(4) . . . . ? C7 C6 N C1 74.5(2) . . . . ? C7 C6 N C5 -163.27(18) . . . . ? C2 C1 N C6 -176.0(2) . . . . ? C2 C1 N C5 60.8(3) . . . . ? C4 C5 N C6 176.43(18) . . . . ? C4 C5 N C1 -59.8(2) . . . . ? O1 C9 O2 C11 178.1(2) . . . . ? C8 C9 O2 C11 -2.1(3) . . . . ? O4 C11 O2 C9 6.1(3) . . . . ? C12 C11 O2 C9 -112.7(2) . . . . ? C13 C11 O2 C9 124.1(2) . . . . ? O3 C10 O4 C11 -178.0(2) . . . . ? C8 C10 O4 C11 -2.1(3) . . . . ? O2 C11 O4 C10 -3.8(3) . . . . ? C12 C11 O4 C10 115.4(2) . . . . ? C13 C11 O4 C10 -121.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.150 _refine_diff_density_min -0.124 _refine_diff_density_rms 0.032 # Attachment '- Phenol.CIF' data_h081810 _database_code_depnum_ccdc_archive 'CCDC 850276' #TrackingRef '- Phenol.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 O5' _chemical_formula_weight 264.27 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' 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)/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 14.348(5) _cell_length_b 11.622(4) _cell_length_c 16.672(6) _cell_angle_alpha 90.00 _cell_angle_beta 103.442(5) _cell_angle_gamma 90.00 _cell_volume 2703.8(17) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.834 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20563 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 26.41 _reflns_number_total 5350 _reflns_number_gt 3828 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0500P)^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 SHELXL _refine_ls_extinction_coef 0.025(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5350 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0774 _refine_ls_R_factor_gt 0.0548 _refine_ls_wR_factor_ref 0.1693 _refine_ls_wR_factor_gt 0.1582 _refine_ls_goodness_of_fit_ref 2.011 _refine_ls_restrained_S_all 2.011 _refine_ls_shift/su_max 0.007 _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 -0.06946(17) 0.60906(18) 0.08983(12) 0.0526(6) Uani 1 1 d . . . C2 C -0.10641(14) 0.77794(17) 0.16009(12) 0.0433(5) Uani 1 1 d . . . C3 C -0.07035(13) 0.85415(17) 0.10034(11) 0.0402(5) Uani 1 1 d . . . C4 C -0.01690(13) 0.79128(16) 0.04599(11) 0.0389(5) Uani 1 1 d . . . C5 C -0.16183(17) 0.5908(2) 0.02831(15) 0.0737(7) Uani 1 1 d . . . H5A H -0.2020 0.5404 0.0512 0.111 Uiso 1 1 calc R . . H5B H -0.1495 0.5569 -0.0207 0.111 Uiso 1 1 calc R . . H5C H -0.1935 0.6634 0.0148 0.111 Uiso 1 1 calc R . . C6 C -0.0159(2) 0.5012(2) 0.11896(15) 0.0865(9) Uani 1 1 d . . . H6A H 0.0429 0.5199 0.1576 0.130 Uiso 1 1 calc R . . H6B H -0.0019 0.4612 0.0727 0.130 Uiso 1 1 calc R . . H6C H -0.0542 0.4529 0.1453 0.130 Uiso 1 1 calc R . . C7 C -0.15507(14) 0.92012(18) 0.04649(13) 0.0533(5) Uani 1 1 d . . . H7A H -0.1319 0.9714 0.0104 0.080 Uiso 1 1 calc R . . H7B H -0.1869 0.9636 0.0812 0.080 Uiso 1 1 calc R . . H7C H -0.1993 0.8665 0.0143 0.080 Uiso 1 1 calc R . . C8 C 0.00122(13) 0.94229(17) 0.15296(12) 0.0461(5) Uani 1 1 d . . . H8A H 0.0196 0.9976 0.1158 0.055 Uiso 1 1 calc R . . H8B H -0.0321 0.9841 0.1882 0.055 Uiso 1 1 calc R . . C9 C 0.09082(14) 0.89133(16) 0.20607(11) 0.0439(5) Uani 1 1 d . . . C10 C 0.17682(15) 0.89692(19) 0.18228(13) 0.0558(6) Uani 1 1 d . . . H10 H 0.1786 0.9336 0.1331 0.067 Uiso 1 1 calc R . . C11 C 0.25976(15) 0.8499(2) 0.22909(13) 0.0602(6) Uani 1 1 d . . . H11 H 0.3166 0.8559 0.2116 0.072 Uiso 1 1 calc R . . C12 C 0.25892(15) 0.7941(2) 0.30166(12) 0.0557(6) Uani 1 1 d . . . C13 C 0.17462(16) 0.7898(2) 0.32786(13) 0.0601(6) Uani 1 1 d . . . H13 H 0.1733 0.7543 0.3776 0.072 Uiso 1 1 calc R . . C14 C 0.09211(15) 0.8381(2) 0.28033(13) 0.0543(6) Uani 1 1 d . . . H14 H 0.0358 0.8346 0.2989 0.065 Uiso 1 1 calc R . . C15 C 0.54780(18) 0.93430(19) 0.14822(14) 0.0607(6) Uani 1 1 d . . . C16 C 0.59017(15) 0.76637(18) 0.08098(12) 0.0468(5) Uani 1 1 d . . . C17 C 0.56313(13) 0.68950(16) 0.14492(11) 0.0409(5) Uani 1 1 d . . . C18 C 0.51217(13) 0.75009(16) 0.20250(11) 0.0389(4) Uani 1 1 d . . . C19 C 0.64588(19) 0.9660(3) 0.20101(18) 0.0923(9) Uani 1 1 d . . . H19A H 0.6804 0.8971 0.2211 0.138 Uiso 1 1 calc R . . H19B H 0.6382 1.0122 0.2468 0.138 Uiso 1 1 calc R . . H19C H 0.6809 1.0087 0.1684 0.138 Uiso 1 1 calc R . . C20 C 0.4852(3) 1.0351(3) 0.12234(19) 0.1180(13) Uani 1 1 d . . . H20A H 0.5151 1.0864 0.0908 0.177 Uiso 1 1 calc R . . H20B H 0.4752 1.0744 0.1703 0.177 Uiso 1 1 calc R . . H20C H 0.4247 1.0099 0.0892 0.177 Uiso 1 1 calc R . . C21 C 0.65426(14) 0.6299(2) 0.19591(13) 0.0560(6) Uani 1 1 d . . . H21A H 0.6972 0.6869 0.2256 0.084 Uiso 1 1 calc R . . H21B H 0.6854 0.5888 0.1595 0.084 Uiso 1 1 calc R . . H21C H 0.6368 0.5771 0.2342 0.084 Uiso 1 1 calc R . . C22 C 0.49447(13) 0.59544(17) 0.09792(12) 0.0468(5) Uani 1 1 d . . . H22A H 0.5279 0.5524 0.0633 0.056 Uiso 1 1 calc R . . H22B H 0.4792 0.5423 0.1379 0.056 Uiso 1 1 calc R . . C23 C 0.40201(14) 0.64114(16) 0.04467(12) 0.0433(5) Uani 1 1 d . . . C24 C 0.39507(15) 0.67209(17) -0.03681(12) 0.0479(5) Uani 1 1 d . . . H24 H 0.4480 0.6632 -0.0596 0.057 Uiso 1 1 calc R . . C25 C 0.31061(15) 0.71596(19) -0.08480(13) 0.0523(5) Uani 1 1 d . . . H25 H 0.3071 0.7358 -0.1395 0.063 Uiso 1 1 calc R . . C26 C 0.23206(14) 0.73032(18) -0.05188(12) 0.0482(5) Uani 1 1 d . . . C27 C 0.23729(14) 0.69840(19) 0.02856(12) 0.0522(5) Uani 1 1 d . . . H27 H 0.1841 0.7069 0.0510 0.063 Uiso 1 1 calc R . . C28 C 0.32148(14) 0.65372(18) 0.07600(12) 0.0499(5) Uani 1 1 d . . . H28 H 0.3240 0.6317 0.1301 0.060 Uiso 1 1 calc R . . O1 O -0.14695(11) 0.81468(13) 0.21001(9) 0.0596(4) Uani 1 1 d . . . O2 O -0.08707(12) 0.66517(12) 0.16123(8) 0.0586(4) Uani 1 1 d . . . O3 O -0.00643(10) 0.67714(11) 0.05310(8) 0.0493(4) Uani 1 1 d . . . O4 O 0.02098(10) 0.83985(12) -0.00119(9) 0.0514(4) Uani 1 1 d . . . O5 O 0.33919(12) 0.74489(18) 0.35053(10) 0.0779(5) Uani 1 1 d . . . H5 H 0.3804 0.7378 0.3241 0.117 Uiso 1 1 calc R . . O6 O 0.62956(12) 0.73257(15) 0.03005(10) 0.0686(5) Uani 1 1 d . . . O7 O 0.56182(12) 0.87660(13) 0.07713(8) 0.0649(5) Uani 1 1 d . . . O8 O 0.50077(11) 0.86382(12) 0.19731(8) 0.0546(4) Uani 1 1 d . . . O9 O 0.47824(10) 0.69947(12) 0.25153(8) 0.0506(4) Uani 1 1 d . . . O10 O 0.15041(11) 0.77379(16) -0.10222(9) 0.0674(5) Uani 1 1 d . . . H10A H 0.1093 0.7821 -0.0758 0.101 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 C1 0.0812(15) 0.0383(12) 0.0498(12) 0.0018(9) 0.0386(11) 0.0006(10) C2 0.0462(11) 0.0442(12) 0.0427(11) -0.0035(9) 0.0166(9) -0.0023(9) C3 0.0416(10) 0.0386(11) 0.0426(10) 0.0011(8) 0.0140(8) 0.0005(8) C4 0.0374(10) 0.0430(12) 0.0366(10) 0.0032(8) 0.0093(8) -0.0018(8) C5 0.0798(17) 0.0704(17) 0.0791(17) -0.0184(13) 0.0353(14) -0.0207(13) C6 0.146(3) 0.0509(16) 0.0778(17) 0.0146(13) 0.0580(18) 0.0243(16) C7 0.0474(12) 0.0506(13) 0.0613(13) 0.0062(10) 0.0117(10) 0.0067(9) C8 0.0508(11) 0.0385(11) 0.0515(11) -0.0024(9) 0.0171(9) -0.0016(9) C9 0.0487(11) 0.0420(11) 0.0416(11) -0.0062(9) 0.0115(9) -0.0040(9) C10 0.0537(13) 0.0686(15) 0.0453(11) 0.0090(10) 0.0120(10) -0.0044(11) C11 0.0449(12) 0.0868(17) 0.0518(13) 0.0035(12) 0.0171(10) -0.0009(11) C12 0.0519(13) 0.0729(15) 0.0404(11) -0.0037(10) 0.0069(10) 0.0035(11) C13 0.0602(14) 0.0817(17) 0.0386(11) 0.0069(11) 0.0120(10) -0.0012(12) C14 0.0504(12) 0.0704(15) 0.0458(12) -0.0028(10) 0.0185(10) -0.0029(11) C15 0.0894(17) 0.0441(13) 0.0572(13) -0.0038(10) 0.0344(13) -0.0028(11) C16 0.0493(11) 0.0510(13) 0.0406(11) -0.0068(9) 0.0113(10) -0.0036(9) C17 0.0403(10) 0.0447(11) 0.0376(10) -0.0002(8) 0.0091(8) 0.0020(8) C18 0.0366(10) 0.0446(12) 0.0333(10) 0.0008(8) 0.0033(8) -0.0015(8) C19 0.0849(18) 0.100(2) 0.098(2) -0.0400(18) 0.0330(17) -0.0271(17) C20 0.184(3) 0.079(2) 0.105(2) 0.0281(18) 0.064(2) 0.054(2) C21 0.0438(11) 0.0693(15) 0.0541(13) 0.0050(11) 0.0100(10) 0.0113(10) C22 0.0493(11) 0.0376(11) 0.0517(12) -0.0036(9) 0.0081(9) 0.0030(9) C23 0.0483(11) 0.0347(11) 0.0447(11) -0.0065(8) 0.0063(9) -0.0017(8) C24 0.0514(12) 0.0485(12) 0.0458(11) -0.0054(9) 0.0156(9) 0.0037(9) C25 0.0587(13) 0.0579(14) 0.0390(11) -0.0021(9) 0.0085(10) 0.0023(10) C26 0.0454(11) 0.0503(12) 0.0454(11) -0.0054(9) 0.0037(9) 0.0010(9) C27 0.0418(11) 0.0669(15) 0.0478(12) -0.0062(10) 0.0102(9) -0.0027(10) C28 0.0478(12) 0.0582(13) 0.0418(11) -0.0012(9) 0.0065(9) -0.0065(10) O1 0.0684(10) 0.0594(10) 0.0623(9) -0.0078(8) 0.0382(8) -0.0020(8) O2 0.0963(12) 0.0415(9) 0.0496(8) 0.0032(6) 0.0405(8) 0.0018(7) O3 0.0615(9) 0.0418(9) 0.0525(8) 0.0025(6) 0.0297(7) 0.0042(6) O4 0.0553(9) 0.0530(9) 0.0512(8) 0.0086(7) 0.0237(7) -0.0019(7) O5 0.0607(10) 0.1177(15) 0.0529(9) 0.0109(10) 0.0083(8) 0.0222(10) O6 0.0808(11) 0.0781(12) 0.0581(10) -0.0060(8) 0.0389(9) 0.0030(9) O7 0.1086(13) 0.0489(10) 0.0434(8) 0.0017(7) 0.0301(8) -0.0003(8) O8 0.0727(10) 0.0457(9) 0.0520(8) -0.0019(7) 0.0281(8) 0.0021(7) O9 0.0492(8) 0.0607(9) 0.0435(8) 0.0076(7) 0.0141(7) 0.0001(7) O10 0.0533(9) 0.0898(12) 0.0540(9) 0.0047(8) 0.0019(7) 0.0140(9) _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 O2 1.430(2) . ? C1 O3 1.441(2) . ? C1 C5 1.490(3) . ? C1 C6 1.492(3) . ? C2 O1 1.199(2) . ? C2 O2 1.339(2) . ? C2 C3 1.511(3) . ? C3 C4 1.505(3) . ? C3 C7 1.538(3) . ? C3 C8 1.567(3) . ? C4 O4 1.196(2) . ? C4 O3 1.337(2) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.503(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C14 1.380(3) . ? C9 C10 1.383(3) . ? C10 C11 1.375(3) . ? C10 H10 0.9300 . ? C11 C12 1.375(3) . ? C11 H11 0.9300 . ? C12 O5 1.372(3) . ? C12 C13 1.379(3) . ? C13 C14 1.381(3) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 O7 1.416(3) . ? C15 O8 1.433(3) . ? C15 C20 1.478(4) . ? C15 C19 1.521(3) . ? C16 O6 1.191(2) . ? C16 O7 1.341(3) . ? C16 C17 1.509(3) . ? C17 C18 1.509(3) . ? C17 C21 1.548(3) . ? C17 C22 1.556(3) . ? C18 O9 1.198(2) . ? C18 O8 1.332(2) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C23 1.511(3) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C28 1.382(3) . ? C23 C24 1.386(3) . ? C24 C25 1.385(3) . ? C24 H24 0.9300 . ? C25 C26 1.374(3) . ? C25 H25 0.9300 . ? C26 O10 1.369(2) . ? C26 C27 1.377(3) . ? C27 C28 1.382(3) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? O5 H5 0.8200 . ? O10 H10A 0.8200 . ? 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 O2 C1 O3 110.68(16) . . ? O2 C1 C5 109.67(18) . . ? O3 C1 C5 109.34(17) . . ? O2 C1 C6 106.83(17) . . ? O3 C1 C6 105.86(19) . . ? C5 C1 C6 114.4(2) . . ? O1 C2 O2 118.10(18) . . ? O1 C2 C3 122.98(19) . . ? O2 C2 C3 118.78(17) . . ? C4 C3 C2 114.37(17) . . ? C4 C3 C7 109.56(15) . . ? C2 C3 C7 109.37(16) . . ? C4 C3 C8 107.16(15) . . ? C2 C3 C8 107.12(15) . . ? C7 C3 C8 109.10(16) . . ? O4 C4 O3 117.88(17) . . ? O4 C4 C3 122.65(18) . . ? O3 C4 C3 119.38(16) . . ? C1 C5 H5A 109.5 . . ? C1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C1 C6 H6A 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C3 115.59(16) . . ? C9 C8 H8A 108.4 . . ? C3 C8 H8A 108.4 . . ? C9 C8 H8B 108.4 . . ? C3 C8 H8B 108.4 . . ? H8A C8 H8B 107.4 . . ? C14 C9 C10 116.84(19) . . ? C14 C9 C8 122.45(18) . . ? C10 C9 C8 120.71(18) . . ? C11 C10 C9 122.0(2) . . ? C11 C10 H10 119.0 . . ? C9 C10 H10 119.0 . . ? C12 C11 C10 120.2(2) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? O5 C12 C11 122.8(2) . . ? O5 C12 C13 118.3(2) . . ? C11 C12 C13 118.9(2) . . ? C12 C13 C14 120.1(2) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C9 C14 C13 121.8(2) . . ? C9 C14 H14 119.1 . . ? C13 C14 H14 119.1 . . ? O7 C15 O8 112.62(17) . . ? O7 C15 C20 109.0(2) . . ? O8 C15 C20 106.6(2) . . ? O7 C15 C19 107.84(19) . . ? O8 C15 C19 107.64(19) . . ? C20 C15 C19 113.2(3) . . ? O6 C16 O7 118.04(19) . . ? O6 C16 C17 123.4(2) . . ? O7 C16 C17 118.31(18) . . ? C18 C17 C16 114.53(17) . . ? C18 C17 C21 109.37(15) . . ? C16 C17 C21 109.25(16) . . ? C18 C17 C22 107.73(15) . . ? C16 C17 C22 107.27(15) . . ? C21 C17 C22 108.51(16) . . ? O9 C18 O8 117.91(18) . . ? O9 C18 C17 122.57(18) . . ? O8 C18 C17 119.47(17) . . ? C15 C19 H19A 109.5 . . ? C15 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C15 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C15 C20 H20A 109.5 . . ? C15 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C15 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C17 C21 H21A 109.5 . . ? C17 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C17 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 C17 114.56(15) . . ? C23 C22 H22A 108.6 . . ? C17 C22 H22A 108.6 . . ? C23 C22 H22B 108.6 . . ? C17 C22 H22B 108.6 . . ? H22A C22 H22B 107.6 . . ? C28 C23 C24 117.84(18) . . ? C28 C23 C22 120.81(18) . . ? C24 C23 C22 121.35(18) . . ? C25 C24 C23 121.0(2) . . ? C25 C24 H24 119.5 . . ? C23 C24 H24 119.5 . . ? C26 C25 C24 120.2(2) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? O10 C26 C25 117.68(19) . . ? O10 C26 C27 122.8(2) . . ? C25 C26 C27 119.51(19) . . ? C26 C27 C28 120.1(2) . . ? C26 C27 H27 120.0 . . ? C28 C27 H27 120.0 . . ? C23 C28 C27 121.32(19) . . ? C23 C28 H28 119.3 . . ? C27 C28 H28 119.3 . . ? C2 O2 C1 120.70(15) . . ? C4 O3 C1 120.92(15) . . ? C12 O5 H5 109.5 . . ? C16 O7 C15 120.85(16) . . ? C18 O8 C15 122.50(16) . . ? C26 O10 H10A 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 O1 C2 C3 C4 176.91(17) . . . . ? O2 C2 C3 C4 1.3(2) . . . . ? O1 C2 C3 C7 -59.8(2) . . . . ? O2 C2 C3 C7 124.62(19) . . . . ? O1 C2 C3 C8 58.3(2) . . . . ? O2 C2 C3 C8 -117.26(18) . . . . ? C2 C3 C4 O4 -175.55(16) . . . . ? C7 C3 C4 O4 61.3(2) . . . . ? C8 C3 C4 O4 -57.0(2) . . . . ? C2 C3 C4 O3 0.8(2) . . . . ? C7 C3 C4 O3 -122.35(18) . . . . ? C8 C3 C4 O3 119.41(18) . . . . ? C4 C3 C8 C9 -58.5(2) . . . . ? C2 C3 C8 C9 64.6(2) . . . . ? C7 C3 C8 C9 -177.08(17) . . . . ? C3 C8 C9 C14 -78.5(2) . . . . ? C3 C8 C9 C10 102.1(2) . . . . ? C14 C9 C10 C11 1.3(3) . . . . ? C8 C9 C10 C11 -179.2(2) . . . . ? C9 C10 C11 C12 0.7(4) . . . . ? C10 C11 C12 O5 179.5(2) . . . . ? C10 C11 C12 C13 -2.2(4) . . . . ? O5 C12 C13 C14 -179.8(2) . . . . ? C11 C12 C13 C14 1.9(4) . . . . ? C10 C9 C14 C13 -1.7(3) . . . . ? C8 C9 C14 C13 178.8(2) . . . . ? C12 C13 C14 C9 0.1(4) . . . . ? O6 C16 C17 C18 -178.98(18) . . . . ? O7 C16 C17 C18 -4.4(2) . . . . ? O6 C16 C17 C21 58.0(3) . . . . ? O7 C16 C17 C21 -127.45(19) . . . . ? O6 C16 C17 C22 -59.5(2) . . . . ? O7 C16 C17 C22 115.11(19) . . . . ? C16 C17 C18 O9 172.93(16) . . . . ? C21 C17 C18 O9 -64.1(2) . . . . ? C22 C17 C18 O9 53.7(2) . . . . ? C16 C17 C18 O8 -4.5(2) . . . . ? C21 C17 C18 O8 118.49(18) . . . . ? C22 C17 C18 O8 -123.76(18) . . . . ? C18 C17 C22 C23 62.1(2) . . . . ? C16 C17 C22 C23 -61.7(2) . . . . ? C21 C17 C22 C23 -179.62(16) . . . . ? C17 C22 C23 C28 -90.7(2) . . . . ? C17 C22 C23 C24 89.1(2) . . . . ? C28 C23 C24 C25 1.0(3) . . . . ? C22 C23 C24 C25 -178.77(18) . . . . ? C23 C24 C25 C26 0.5(3) . . . . ? C24 C25 C26 O10 -179.85(19) . . . . ? C24 C25 C26 C27 -1.4(3) . . . . ? O10 C26 C27 C28 179.21(19) . . . . ? C25 C26 C27 C28 0.9(3) . . . . ? C24 C23 C28 C27 -1.6(3) . . . . ? C22 C23 C28 C27 178.20(19) . . . . ? C26 C27 C28 C23 0.7(3) . . . . ? O1 C2 O2 C1 158.84(19) . . . . ? C3 C2 O2 C1 -25.4(3) . . . . ? O3 C1 O2 C2 44.3(3) . . . . ? C5 C1 O2 C2 -76.4(2) . . . . ? C6 C1 O2 C2 159.1(2) . . . . ? O4 C4 O3 C1 -162.71(17) . . . . ? C3 C4 O3 C1 20.7(2) . . . . ? O2 C1 O3 C4 -41.9(2) . . . . ? C5 C1 O3 C4 79.1(2) . . . . ? C6 C1 O3 C4 -157.26(18) . . . . ? O6 C16 O7 C15 -156.6(2) . . . . ? C17 C16 O7 C15 28.5(3) . . . . ? O8 C15 O7 C16 -41.6(3) . . . . ? C20 C15 O7 C16 -159.6(2) . . . . ? C19 C15 O7 C16 77.1(3) . . . . ? O9 C18 O8 C15 172.35(17) . . . . ? C17 C18 O8 C15 -10.1(3) . . . . ? O7 C15 O8 C18 31.8(3) . . . . ? C20 C15 O8 C18 151.3(2) . . . . ? C19 C15 O8 C18 -86.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 26.41 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.642 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.048 # Attachment '- Six mem amine.CIF' data_f110309 _database_code_depnum_ccdc_archive 'CCDC 850277' #TrackingRef '- Six mem amine.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H29 N O4' _chemical_formula_weight 359.45 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)/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 11.210(5) _cell_length_b 16.029(7) _cell_length_c 11.499(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.731(7) _cell_angle_gamma 90.00 _cell_volume 2015.5(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.185 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.214 _exptl_absorpt_correction_T_max 0.360 _exptl_absorpt_process_details 'psi scan' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15829 _diffrn_reflns_av_R_equivalents 0.0665 _diffrn_reflns_av_sigmaI/netI 0.0432 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 26.42 _reflns_number_total 4031 _reflns_number_gt 2601 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0500P)^2^+0.0325P] 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 0.032(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4031 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0712 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1225 _refine_ls_wR_factor_gt 0.1110 _refine_ls_goodness_of_fit_ref 1.175 _refine_ls_restrained_S_all 1.175 _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 C1 C 0.39646(17) 0.67782(10) 0.73939(18) 0.0748(5) Uani 1 1 d . . . H1A H 0.3571 0.6830 0.6557 0.090 Uiso 1 1 calc R . . H1B H 0.3332 0.6788 0.7849 0.090 Uiso 1 1 calc R . . C2 C 0.4635(2) 0.59545(11) 0.7595(2) 0.0869(6) Uani 1 1 d . . . H2A H 0.5210 0.5919 0.7078 0.104 Uiso 1 1 calc R . . H2B H 0.4053 0.5501 0.7390 0.104 Uiso 1 1 calc R . . C3 C 0.5317(2) 0.58633(11) 0.88813(19) 0.0848(6) Uani 1 1 d . . . H3A H 0.4737 0.5795 0.9388 0.102 Uiso 1 1 calc R . . H3B H 0.5831 0.5370 0.8964 0.102 Uiso 1 1 calc R . . C4 C 0.60949(17) 0.66219(11) 0.92669(18) 0.0789(5) Uani 1 1 d . . . H4A H 0.6765 0.6631 0.8858 0.095 Uiso 1 1 calc R . . H4B H 0.6442 0.6588 1.0116 0.095 Uiso 1 1 calc R . . C5 C 0.53667(16) 0.74197(10) 0.90007(15) 0.0668(5) Uani 1 1 d . . . H5A H 0.4747 0.7436 0.9471 0.080 Uiso 1 1 calc R . . H5B H 0.5906 0.7893 0.9228 0.080 Uiso 1 1 calc R . . C6 C 0.41252(14) 0.82637(9) 0.74576(15) 0.0619(4) Uani 1 1 d . . . H6A H 0.3515 0.8307 0.7936 0.074 Uiso 1 1 calc R . . H6B H 0.3697 0.8249 0.6627 0.074 Uiso 1 1 calc R . . C7 C 0.49264(14) 0.90387(9) 0.76627(14) 0.0581(4) Uani 1 1 d . . . H7A H 0.5140 0.9164 0.8508 0.070 Uiso 1 1 calc R . . H7B H 0.5677 0.8932 0.7400 0.070 Uiso 1 1 calc R . . C8 C 0.42766(14) 0.97837(9) 0.69909(13) 0.0566(4) Uani 1 1 d . . . H8A H 0.3473 0.9832 0.7169 0.068 Uiso 1 1 calc R . . H8B H 0.4161 0.9679 0.6142 0.068 Uiso 1 1 calc R . . C9 C 0.49561(13) 1.06288(8) 0.72835(12) 0.0488(4) Uani 1 1 d . . . C10 C 0.62315(13) 1.05144(9) 0.70799(13) 0.0503(4) Uani 1 1 d . . . C11 C 0.49075(14) 1.08547(8) 0.85530(13) 0.0494(4) Uani 1 1 d . . . C12 C 0.71391(13) 1.09478(10) 0.91226(13) 0.0566(4) Uani 1 1 d . . . C13 C 0.75188(16) 1.18392(11) 0.90623(17) 0.0739(5) Uani 1 1 d . . . H13A H 0.6953 1.2119 0.8435 0.111 Uiso 1 1 calc R . . H13B H 0.8324 1.1862 0.8904 0.111 Uiso 1 1 calc R . . H13C H 0.7523 1.2109 0.9809 0.111 Uiso 1 1 calc R . . C14 C 0.79551(17) 1.04488(12) 1.00840(16) 0.0792(5) Uani 1 1 d . . . H14A H 0.7984 1.0707 1.0843 0.119 Uiso 1 1 calc R . . H14B H 0.8764 1.0428 0.9935 0.119 Uiso 1 1 calc R . . H14C H 0.7639 0.9893 1.0089 0.119 Uiso 1 1 calc R . . C15 C 0.42711(14) 1.13052(9) 0.64180(14) 0.0581(4) Uani 1 1 d . . . H15A H 0.4265 1.1137 0.5606 0.070 Uiso 1 1 calc R . . H15B H 0.3429 1.1329 0.6499 0.070 Uiso 1 1 calc R . . C16 C 0.48195(13) 1.21682(9) 0.66223(13) 0.0560(4) Uani 1 1 d . . . C17 C 0.45192(15) 1.27032(10) 0.74598(15) 0.0623(4) Uani 1 1 d . . . H17 H 0.3937 1.2539 0.7878 0.075 Uiso 1 1 calc R . . C18 C 0.50636(17) 1.34725(11) 0.76857(18) 0.0749(5) Uani 1 1 d . . . H18 H 0.4846 1.3821 0.8252 0.090 Uiso 1 1 calc R . . C19 C 0.59248(18) 1.37295(12) 0.7081(2) 0.0831(6) Uani 1 1 d . . . H19 H 0.6304 1.4246 0.7245 0.100 Uiso 1 1 calc R . . C20 C 0.62207(18) 1.32165(13) 0.6232(2) 0.0836(6) Uani 1 1 d . . . H20 H 0.6797 1.3388 0.5812 0.100 Uiso 1 1 calc R . . C21 C 0.56674(16) 1.24469(11) 0.59970(16) 0.0720(5) Uani 1 1 d . . . H21 H 0.5867 1.2110 0.5410 0.086 Uiso 1 1 calc R . . N N 0.47826(11) 0.74830(7) 0.77443(12) 0.0568(3) Uani 1 1 d . . . O1 O 0.64294(10) 1.03345(8) 0.61304(10) 0.0719(3) Uani 1 1 d . . . O2 O 0.71778(9) 1.05385(7) 0.80184(9) 0.0659(3) Uani 1 1 d . . . O3 O 0.39618(10) 1.09489(7) 0.88617(10) 0.0657(3) Uani 1 1 d . . . O4 O 0.59444(10) 1.09139(7) 0.93809(9) 0.0660(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0733(11) 0.0683(11) 0.0806(12) -0.0158(9) 0.0122(10) -0.0234(9) C2 0.1065(15) 0.0569(11) 0.1003(16) -0.0190(10) 0.0295(13) -0.0207(10) C3 0.1000(15) 0.0602(11) 0.0979(15) -0.0014(9) 0.0301(13) -0.0057(10) C4 0.0771(12) 0.0710(12) 0.0863(13) -0.0022(9) 0.0129(10) 0.0007(9) C5 0.0690(11) 0.0619(10) 0.0680(11) -0.0131(8) 0.0116(9) -0.0066(8) C6 0.0543(9) 0.0631(10) 0.0668(10) -0.0118(8) 0.0101(8) -0.0087(7) C7 0.0542(9) 0.0567(9) 0.0600(9) -0.0071(7) 0.0055(7) -0.0055(7) C8 0.0513(9) 0.0626(9) 0.0540(9) -0.0086(7) 0.0078(7) -0.0043(7) C9 0.0452(8) 0.0555(8) 0.0443(8) -0.0040(6) 0.0070(6) 0.0005(6) C10 0.0494(9) 0.0547(8) 0.0464(9) -0.0036(6) 0.0096(7) 0.0002(6) C11 0.0492(9) 0.0489(8) 0.0501(9) -0.0036(6) 0.0111(7) -0.0009(6) C12 0.0454(8) 0.0726(10) 0.0486(9) -0.0114(7) 0.0034(7) 0.0021(7) C13 0.0650(11) 0.0734(11) 0.0788(12) -0.0064(9) 0.0061(9) -0.0008(8) C14 0.0695(11) 0.0921(13) 0.0686(11) 0.0028(9) -0.0007(9) 0.0118(9) C15 0.0489(9) 0.0697(10) 0.0522(9) 0.0008(7) 0.0035(7) 0.0042(7) C16 0.0496(8) 0.0617(9) 0.0536(9) 0.0110(7) 0.0044(7) 0.0091(7) C17 0.0598(10) 0.0606(10) 0.0681(10) 0.0095(8) 0.0175(9) 0.0065(8) C18 0.0810(12) 0.0596(10) 0.0850(13) 0.0020(9) 0.0202(10) 0.0049(9) C19 0.0772(13) 0.0637(11) 0.1067(15) 0.0124(11) 0.0166(12) -0.0041(9) C20 0.0756(13) 0.0790(13) 0.1032(15) 0.0243(11) 0.0350(12) -0.0008(10) C21 0.0727(11) 0.0776(12) 0.0701(12) 0.0118(9) 0.0255(10) 0.0100(9) N 0.0554(7) 0.0534(7) 0.0624(8) -0.0139(6) 0.0143(6) -0.0100(6) O1 0.0665(7) 0.0997(9) 0.0526(7) -0.0122(6) 0.0200(6) 0.0018(6) O2 0.0462(6) 0.0933(8) 0.0560(7) -0.0197(5) 0.0064(5) 0.0067(5) O3 0.0554(7) 0.0797(7) 0.0666(7) -0.0075(5) 0.0233(6) 0.0002(5) O4 0.0529(6) 0.0971(8) 0.0469(6) -0.0168(5) 0.0083(5) -0.0002(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 N 1.455(2) . ? C1 C2 1.512(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.515(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.505(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.512(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 N 1.452(2) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N 1.453(2) . ? C6 C7 1.521(2) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.518(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.554(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.510(2) . ? C9 C11 1.517(2) . ? C9 C15 1.555(2) . ? C10 O1 1.1963(17) . ? C10 O2 1.3367(18) . ? C11 O3 1.1995(16) . ? C11 O4 1.3337(18) . ? C12 O4 1.4354(18) . ? C12 O2 1.4383(18) . ? C12 C13 1.497(2) . ? C12 C14 1.501(2) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.511(2) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.385(2) . ? C16 C21 1.386(2) . ? C17 C18 1.375(2) . ? C17 H17 0.9300 . ? C18 C19 1.371(2) . ? C18 H18 0.9300 . ? C19 C20 1.372(3) . ? C19 H19 0.9300 . ? C20 C21 1.380(3) . ? C20 H20 0.9300 . ? C21 H21 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 N C1 C2 111.98(16) . . ? N C1 H1A 109.2 . . ? C2 C1 H1A 109.2 . . ? N C1 H1B 109.2 . . ? C2 C1 H1B 109.2 . . ? H1A C1 H1B 107.9 . . ? C1 C2 C3 111.14(15) . . ? C1 C2 H2A 109.4 . . ? C3 C2 H2A 109.4 . . ? C1 C2 H2B 109.4 . . ? C3 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? C4 C3 C2 110.16(15) . . ? C4 C3 H3A 109.6 . . ? C2 C3 H3A 109.6 . . ? C4 C3 H3B 109.6 . . ? C2 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? C3 C4 C5 111.83(17) . . ? C3 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? C3 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 107.9 . . ? N C5 C4 111.44(13) . . ? N C5 H5A 109.3 . . ? C4 C5 H5A 109.3 . . ? N C5 H5B 109.3 . . ? C4 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? N C6 C7 114.57(13) . . ? N C6 H6A 108.6 . . ? C7 C6 H6A 108.6 . . ? N C6 H6B 108.6 . . ? C7 C6 H6B 108.6 . . ? H6A C6 H6B 107.6 . . ? C8 C7 C6 111.28(14) . . ? C8 C7 H7A 109.4 . . ? C6 C7 H7A 109.4 . . ? C8 C7 H7B 109.4 . . ? C6 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? C7 C8 C9 114.71(13) . . ? C7 C8 H8A 108.6 . . ? C9 C8 H8A 108.6 . . ? C7 C8 H8B 108.6 . . ? C9 C8 H8B 108.6 . . ? H8A C8 H8B 107.6 . . ? C10 C9 C11 114.47(12) . . ? C10 C9 C8 107.23(11) . . ? C11 C9 C8 107.25(11) . . ? C10 C9 C15 109.65(11) . . ? C11 C9 C15 109.40(12) . . ? C8 C9 C15 108.65(12) . . ? O1 C10 O2 118.03(13) . . ? O1 C10 C9 122.90(13) . . ? O2 C10 C9 118.78(12) . . ? O3 C11 O4 117.90(13) . . ? O3 C11 C9 122.45(13) . . ? O4 C11 C9 119.58(12) . . ? O4 C12 O2 112.12(11) . . ? O4 C12 C13 109.48(12) . . ? O2 C12 C13 109.29(13) . . ? O4 C12 C14 105.81(13) . . ? O2 C12 C14 105.97(13) . . ? C13 C12 C14 114.17(14) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C9 114.34(12) . . ? C16 C15 H15A 108.7 . . ? C9 C15 H15A 108.7 . . ? C16 C15 H15B 108.7 . . ? C9 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C17 C16 C21 117.43(15) . . ? C17 C16 C15 121.46(14) . . ? C21 C16 C15 121.09(14) . . ? C18 C17 C16 121.38(15) . . ? C18 C17 H17 119.3 . . ? C16 C17 H17 119.3 . . ? C19 C18 C17 120.42(17) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C18 C19 C20 119.23(18) . . ? C18 C19 H19 120.4 . . ? C20 C19 H19 120.4 . . ? C19 C20 C21 120.40(17) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C20 C21 C16 121.10(16) . . ? C20 C21 H21 119.5 . . ? C16 C21 H21 119.5 . . ? C5 N C6 112.39(12) . . ? C5 N C1 109.86(13) . . ? C6 N C1 110.42(13) . . ? C10 O2 C12 123.56(11) . . ? C11 O4 C12 124.13(11) . . ? 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 N C1 C2 C3 56.1(2) . . . . ? C1 C2 C3 C4 -51.2(2) . . . . ? C2 C3 C4 C5 51.6(2) . . . . ? C3 C4 C5 N -56.5(2) . . . . ? N C6 C7 C8 161.68(13) . . . . ? C6 C7 C8 C9 172.12(12) . . . . ? C7 C8 C9 C10 54.41(16) . . . . ? C7 C8 C9 C11 -68.99(15) . . . . ? C7 C8 C9 C15 172.85(12) . . . . ? C11 C9 C10 O1 179.91(13) . . . . ? C8 C9 C10 O1 61.08(18) . . . . ? C15 C9 C10 O1 -56.71(18) . . . . ? C11 C9 C10 O2 6.27(18) . . . . ? C8 C9 C10 O2 -112.56(14) . . . . ? C15 C9 C10 O2 129.65(14) . . . . ? C10 C9 C11 O3 -178.39(13) . . . . ? C8 C9 C11 O3 -59.57(17) . . . . ? C15 C9 C11 O3 58.10(17) . . . . ? C10 C9 C11 O4 -1.69(18) . . . . ? C8 C9 C11 O4 117.12(14) . . . . ? C15 C9 C11 O4 -125.20(13) . . . . ? C10 C9 C15 C16 -64.46(16) . . . . ? C11 C9 C15 C16 61.85(16) . . . . ? C8 C9 C15 C16 178.64(12) . . . . ? C9 C15 C16 C17 -85.05(18) . . . . ? C9 C15 C16 C21 93.35(17) . . . . ? C21 C16 C17 C18 -1.7(2) . . . . ? C15 C16 C17 C18 176.79(15) . . . . ? C16 C17 C18 C19 0.0(3) . . . . ? C17 C18 C19 C20 1.2(3) . . . . ? C18 C19 C20 C21 -0.7(3) . . . . ? C19 C20 C21 C16 -1.1(3) . . . . ? C17 C16 C21 C20 2.2(2) . . . . ? C15 C16 C21 C20 -176.25(16) . . . . ? C4 C5 N C6 -177.24(13) . . . . ? C4 C5 N C1 59.39(18) . . . . ? C7 C6 N C5 63.37(17) . . . . ? C7 C6 N C1 -173.58(13) . . . . ? C2 C1 N C5 -59.68(18) . . . . ? C2 C1 N C6 175.81(14) . . . . ? O1 C10 O2 C12 163.03(14) . . . . ? C9 C10 O2 C12 -23.0(2) . . . . ? O4 C12 O2 C10 32.25(19) . . . . ? C13 C12 O2 C10 -89.33(17) . . . . ? C14 C12 O2 C10 147.22(14) . . . . ? O3 C11 O4 C12 -169.74(13) . . . . ? C9 C11 O4 C12 13.42(19) . . . . ? O2 C12 O4 C11 -27.07(19) . . . . ? C13 C12 O4 C11 94.40(16) . . . . ? C14 C12 O4 C11 -142.14(15) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.184 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.042 # Attachment '- triazole.CIF' data_h _database_code_depnum_ccdc_archive 'CCDC 850278' #TrackingRef '- triazole.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H21 N3 O4' _chemical_formula_weight 355.39 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 Iba2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'x+1, -y+1, z+1/2' '-x+1, y+1, z+1/2' _cell_length_a 17.443(4) _cell_length_b 21.703(5) _cell_length_c 9.844(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3726.8(15) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.173 _exptl_absorpt_correction_T_max 0.319 _exptl_absorpt_process_details 'psi scan' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'omega sacn' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9632 _diffrn_reflns_av_R_equivalents 0.1257 _diffrn_reflns_av_sigmaI/netI 0.1338 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 26.45 _reflns_number_total 3477 _reflns_number_gt 1667 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _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 0(4) _refine_ls_number_reflns 3477 _refine_ls_number_parameters 238 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.2470 _refine_ls_R_factor_gt 0.1313 _refine_ls_wR_factor_ref 0.3070 _refine_ls_wR_factor_gt 0.2684 _refine_ls_goodness_of_fit_ref 1.390 _refine_ls_restrained_S_all 1.393 _refine_ls_shift/su_max 0.027 _refine_ls_shift/su_mean 0.005 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 0.1280(5) 0.2811(5) -0.0174(9) 0.067(3) Uani 1 1 d . . . C2 C 0.2495(4) 0.2922(5) 0.0921(11) 0.072(3) Uani 1 1 d . . . C3 C 0.1385(4) 0.3088(4) 0.2265(9) 0.045(2) Uani 1 1 d . . . C4 C 0.0879(3) 0.2881(3) 0.1119(7) 0.0331(17) Uani 1 1 d . . . C5 C 0.0478(5) 0.2286(4) 0.1520(13) 0.089(4) Uani 1 1 d . . . H5A H 0.0144 0.2158 0.0800 0.133 Uiso 1 1 calc R . . H5B H 0.0184 0.2352 0.2331 0.133 Uiso 1 1 calc R . . H5C H 0.0854 0.1971 0.1683 0.133 Uiso 1 1 calc R . . C6 C 0.2686(7) 0.2270(7) 0.1134(12) 0.123(6) Uani 1 1 d . . . H6A H 0.3013 0.2231 0.1914 0.184 Uiso 1 1 calc R . . H6B H 0.2947 0.2113 0.0348 0.184 Uiso 1 1 calc R . . H6C H 0.2224 0.2039 0.1280 0.184 Uiso 1 1 calc R . . C7 C 0.3186(6) 0.3274(10) 0.063(2) 0.199(9) Uani 1 1 d . . . H7A H 0.3047 0.3677 0.0314 0.298 Uiso 1 1 calc R . . H7B H 0.3480 0.3067 -0.0051 0.298 Uiso 1 1 calc R . . H7C H 0.3486 0.3312 0.1447 0.298 Uiso 1 1 calc R . . C8 C 0.0253(3) 0.3382(3) 0.0953(8) 0.0387(18) Uani 1 1 d . . . H8A H -0.0099 0.3255 0.0244 0.046 Uiso 1 1 calc R . . H8B H -0.0035 0.3414 0.1793 0.046 Uiso 1 1 calc R . . C9 C 0.0564(4) 0.3993(5) 0.0608(10) 0.058(3) Uani 1 1 d . . . C10 C 0.0789(5) 0.4488(5) 0.1372(10) 0.060(3) Uani 1 1 d . . . H10 H 0.0766 0.4511 0.2314 0.072 Uiso 1 1 calc R . . C11 C 0.1356(4) 0.5534(4) 0.0900(10) 0.061(2) Uani 1 1 d . . . H11A H 0.1140 0.5834 0.0278 0.074 Uiso 1 1 calc R . . H11B H 0.1202 0.5648 0.1813 0.074 Uiso 1 1 calc R . . C12 C 0.2182(5) 0.5555(4) 0.0808(10) 0.065(2) Uani 1 1 d D . . C13 C 0.2672(6) 0.5407(7) 0.1828(14) 0.127(5) Uani 1 1 d D . . H13 H 0.2478 0.5251 0.2639 0.153 Uiso 1 1 calc R . . C14 C 0.3453(7) 0.5484(8) 0.1678(18) 0.165(8) Uani 1 1 d D . . H14 H 0.3773 0.5424 0.2422 0.198 Uiso 1 1 calc R . . C15 C 0.3764(6) 0.5646(6) 0.0460(15) 0.115(5) Uani 1 1 d D . . C16 C 0.3282(6) 0.5831(8) -0.0575(16) 0.148(6) Uani 1 1 d D . . H16 H 0.3477 0.5994 -0.1378 0.177 Uiso 1 1 calc R . . C17 C 0.2502(5) 0.5768(6) -0.0383(12) 0.108(4) Uani 1 1 d D . . H17 H 0.2176 0.5875 -0.1092 0.130 Uiso 1 1 calc R . . C18 C 0.4591(8) 0.5725(7) 0.027(3) 0.197(11) Uani 1 1 d . . . H18 H 0.4870 0.5591 0.1017 0.236 Uiso 1 1 calc R . . C19 C 0.4998(10) 0.5921(10) -0.062(3) 0.232(13) Uani 1 1 d . . . H19A H 0.4783 0.6069 -0.1421 0.279 Uiso 1 1 calc R . . H19B H 0.5527 0.5925 -0.0504 0.279 Uiso 1 1 calc R . . N1 N 0.0708(4) 0.4174(5) -0.0714(8) 0.081(3) Uani 1 1 d . . . N2 N 0.1002(5) 0.4739(5) -0.0712(9) 0.085(3) Uani 1 1 d . . . N3 N 0.1040(3) 0.4918(4) 0.0577(8) 0.059(2) Uani 1 1 d . . . O1 O 0.2020(3) 0.2957(3) -0.0283(6) 0.082(2) Uani 1 1 d . . . O2 O 0.2104(3) 0.3167(3) 0.2051(6) 0.080(2) Uani 1 1 d . . . O3 O 0.0952(4) 0.2616(4) -0.1182(7) 0.105(3) Uani 1 1 d . . . O4 O 0.1170(3) 0.3208(3) 0.3394(6) 0.077(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 0.076(6) 0.095(8) 0.031(5) -0.016(5) -0.014(5) 0.031(5) C2 0.045(5) 0.105(8) 0.067(6) -0.018(6) 0.013(5) 0.005(5) C3 0.020(4) 0.045(5) 0.069(6) 0.007(4) 0.003(4) 0.017(3) C4 0.026(3) 0.036(5) 0.037(4) -0.004(3) 0.005(3) -0.006(3) C5 0.057(5) 0.055(7) 0.155(11) -0.029(7) 0.023(6) -0.014(5) C6 0.094(8) 0.188(15) 0.087(9) -0.062(9) -0.029(7) 0.075(9) C7 0.041(6) 0.36(3) 0.196(18) -0.061(17) 0.024(9) -0.072(10) C8 0.020(3) 0.036(5) 0.060(5) 0.004(4) -0.004(3) -0.005(3) C9 0.033(4) 0.087(8) 0.053(6) -0.004(6) -0.009(4) 0.028(5) C10 0.046(4) 0.080(8) 0.053(5) 0.009(6) -0.001(4) 0.022(5) C11 0.060(5) 0.029(5) 0.095(7) -0.015(5) 0.008(5) -0.007(4) C12 0.066(6) 0.033(5) 0.096(7) 0.009(5) -0.017(6) 0.002(4) C13 0.063(7) 0.148(13) 0.171(13) 0.066(10) -0.011(9) -0.018(7) C14 0.124(14) 0.155(16) 0.215(19) 0.097(15) -0.058(13) -0.009(11) C15 0.068(7) 0.067(9) 0.209(17) -0.019(9) 0.001(10) 0.031(6) C16 0.082(9) 0.154(14) 0.206(18) 0.032(13) 0.021(11) 0.019(9) C17 0.065(7) 0.139(12) 0.121(10) 0.027(9) 0.008(7) -0.018(6) C18 0.075(9) 0.093(11) 0.42(3) -0.039(16) 0.044(15) -0.039(8) C19 0.105(12) 0.21(2) 0.38(3) -0.12(2) 0.086(19) -0.062(15) N1 0.080(6) 0.120(8) 0.042(5) 0.013(5) -0.002(4) -0.024(5) N2 0.113(7) 0.090(8) 0.053(6) 0.011(5) 0.009(5) -0.020(6) N3 0.052(4) 0.079(6) 0.047(5) 0.013(5) 0.006(4) 0.010(4) O1 0.039(3) 0.163(7) 0.044(4) 0.020(4) 0.011(3) 0.008(3) O2 0.058(4) 0.118(6) 0.065(4) -0.057(4) -0.012(3) 0.011(4) O3 0.074(4) 0.187(9) 0.055(5) -0.046(5) -0.009(3) 0.028(5) O4 0.066(4) 0.122(7) 0.043(4) -0.013(3) 0.005(3) 0.025(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 C1 O3 1.221(10) . ? C1 O1 1.333(10) . ? C1 C4 1.461(10) . ? C2 O2 1.409(11) . ? C2 O1 1.449(11) . ? C2 C7 1.454(14) . ? C2 C6 1.469(15) . ? C3 O4 1.201(9) . ? C3 O2 1.283(9) . ? C3 C4 1.501(10) . ? C4 C5 1.522(11) . ? C4 C8 1.549(9) . ? C8 C9 1.472(11) . ? C9 C10 1.368(12) . ? C9 N1 1.382(11) . ? C10 N3 1.294(11) . ? C11 C12 1.444(11) . ? C11 N3 1.481(11) . ? C12 C13 1.357(9) . ? C12 C17 1.378(9) . ? C13 C14 1.382(9) . ? C14 C15 1.362(9) . ? C15 C16 1.381(9) . ? C15 C18 1.465(18) . ? C16 C17 1.380(8) . ? C18 C19 1.20(3) . ? N1 N2 1.328(11) . ? N2 N3 1.329(10) . ? 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 O3 C1 O1 118.1(8) . . ? O3 C1 C4 121.4(8) . . ? O1 C1 C4 120.6(7) . . ? O2 C2 O1 110.4(6) . . ? O2 C2 C7 110.9(11) . . ? O1 C2 C7 106.7(11) . . ? O2 C2 C6 111.1(9) . . ? O1 C2 C6 107.2(8) . . ? C7 C2 C6 110.3(11) . . ? O4 C3 O2 115.3(8) . . ? O4 C3 C4 125.2(6) . . ? O2 C3 C4 119.4(8) . . ? C1 C4 C3 113.9(6) . . ? C1 C4 C5 110.9(7) . . ? C3 C4 C5 109.2(7) . . ? C1 C4 C8 108.6(6) . . ? C3 C4 C8 106.5(6) . . ? C5 C4 C8 107.4(6) . . ? C9 C8 C4 113.4(5) . . ? C10 C9 N1 104.1(9) . . ? C10 C9 C8 133.3(9) . . ? N1 C9 C8 122.6(9) . . ? N3 C10 C9 109.3(9) . . ? C12 C11 N3 112.7(7) . . ? C13 C12 C17 117.0(10) . . ? C13 C12 C11 125.0(10) . . ? C17 C12 C11 117.9(9) . . ? C12 C13 C14 120.9(12) . . ? C15 C14 C13 121.2(13) . . ? C14 C15 C16 118.9(12) . . ? C14 C15 C18 122.4(15) . . ? C16 C15 C18 118.0(15) . . ? C17 C16 C15 118.0(12) . . ? C12 C17 C16 123.3(11) . . ? C19 C18 C15 136(3) . . ? N2 N1 C9 109.3(8) . . ? N3 N2 N1 106.9(7) . . ? C10 N3 N2 110.4(8) . . ? C10 N3 C11 130.4(9) . . ? N2 N3 C11 119.2(8) . . ? C1 O1 C2 118.5(7) . . ? C3 O2 C2 123.5(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 C1 C4 C3 176.2(9) . . . . ? O1 C1 C4 C3 -3.5(11) . . . . ? O3 C1 C4 C5 52.6(12) . . . . ? O1 C1 C4 C5 -127.2(9) . . . . ? O3 C1 C4 C8 -65.3(11) . . . . ? O1 C1 C4 C8 115.0(8) . . . . ? O4 C3 C4 C1 175.7(8) . . . . ? O2 C3 C4 C1 -1.9(11) . . . . ? O4 C3 C4 C5 -59.7(10) . . . . ? O2 C3 C4 C5 122.7(8) . . . . ? O4 C3 C4 C8 56.0(10) . . . . ? O2 C3 C4 C8 -121.6(8) . . . . ? C1 C4 C8 C9 -62.0(9) . . . . ? C3 C4 C8 C9 61.1(8) . . . . ? C5 C4 C8 C9 178.0(8) . . . . ? C4 C8 C9 C10 -91.5(10) . . . . ? C4 C8 C9 N1 86.8(8) . . . . ? N1 C9 C10 N3 0.1(8) . . . . ? C8 C9 C10 N3 178.6(7) . . . . ? N3 C11 C12 C13 -86.8(13) . . . . ? N3 C11 C12 C17 96.4(11) . . . . ? C17 C12 C13 C14 2(2) . . . . ? C11 C12 C13 C14 -175.2(13) . . . . ? C12 C13 C14 C15 -7(3) . . . . ? C13 C14 C15 C16 10(3) . . . . ? C13 C14 C15 C18 -179.4(14) . . . . ? C14 C15 C16 C17 -8(2) . . . . ? C18 C15 C16 C17 -178.7(13) . . . . ? C13 C12 C17 C16 0(2) . . . . ? C11 C12 C17 C16 177.5(12) . . . . ? C15 C16 C17 C12 3(2) . . . . ? C14 C15 C18 C19 -171(2) . . . . ? C16 C15 C18 C19 0(3) . . . . ? C10 C9 N1 N2 0.3(9) . . . . ? C8 C9 N1 N2 -178.5(7) . . . . ? C9 N1 N2 N3 -0.5(10) . . . . ? C9 C10 N3 N2 -0.4(9) . . . . ? C9 C10 N3 C11 -179.0(7) . . . . ? N1 N2 N3 C10 0.6(10) . . . . ? N1 N2 N3 C11 179.4(7) . . . . ? C12 C11 N3 C10 102.1(10) . . . . ? C12 C11 N3 N2 -76.4(10) . . . . ? O3 C1 O1 C2 -152.9(10) . . . . ? C4 C1 O1 C2 26.8(12) . . . . ? O2 C2 O1 C1 -42.4(12) . . . . ? C7 C2 O1 C1 -163.0(11) . . . . ? C6 C2 O1 C1 78.9(10) . . . . ? O4 C3 O2 C2 164.7(9) . . . . ? C4 C3 O2 C2 -17.5(13) . . . . ? O1 C2 O2 C3 38.5(13) . . . . ? C7 C2 O2 C3 156.6(12) . . . . ? C6 C2 O2 C3 -80.3(11) . . . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 26.45 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.571 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.086