# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Ashwini Nangia' _publ_contact_author_address ; P O Central University Hyderabad 500046 Hyderabad AP India 500046 ; _publ_contact_author_email ashwini.nangia@gmail.com loop_ _publ_author_name A.Nangia B.Sarma R.Thakuria N.Nath data_Mrtz-adipate _database_code_depnum_ccdc_archive 'CCDC 797387' #TrackingRef '- Mrtz-adipate.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H24 N3 O2' _chemical_formula_weight 338.42 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 10.631(9) _cell_length_b 9.315(8) _cell_length_c 18.052(15) _cell_angle_alpha 90.00 _cell_angle_beta 103.771(13) _cell_angle_gamma 90.00 _cell_volume 1736(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3875 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 28.12 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 724 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9766 _exptl_absorpt_correction_T_max 0.9849 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany ; _diffrn_ambient_temperature 100(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 8744 _diffrn_reflns_av_R_equivalents 0.0570 _diffrn_reflns_av_sigmaI/netI 0.0723 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 28.12 _reflns_number_total 3813 _reflns_number_gt 3127 _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^)+(0.1631P)^2^+3.3282P] 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 3813 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0921 _refine_ls_R_factor_gt 0.0784 _refine_ls_wR_factor_ref 0.2418 _refine_ls_wR_factor_gt 0.2147 _refine_ls_goodness_of_fit_ref 0.869 _refine_ls_restrained_S_all 0.869 _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 0.6927(3) 0.8505(3) 0.13935(17) 0.0303(6) Uani 1 1 d . . . H1 H 0.7227 0.8095 0.0985 0.036 Uiso 1 1 calc R . . C2 C 0.7817(3) 0.8789(3) 0.20642(17) 0.0297(6) Uani 1 1 d . . . H2 H 0.8708 0.8570 0.2122 0.036 Uiso 1 1 calc R . . C3 C 0.7375(2) 0.9407(3) 0.26579(16) 0.0269(6) Uani 1 1 d . . . H3 H 0.7968 0.9614 0.3129 0.032 Uiso 1 1 calc R . . C4 C 0.6076(2) 0.9720(3) 0.25631(15) 0.0208(5) Uani 1 1 d . . . C5 C 0.5532(3) 1.0440(3) 0.31652(15) 0.0241(6) Uani 1 1 d . . . H5A H 0.4981 1.1261 0.2940 0.029 Uiso 1 1 calc R . . H5B H 0.6247 1.0810 0.3577 0.029 Uiso 1 1 calc R . . C6 C 0.4734(2) 0.9357(3) 0.34892(14) 0.0213(5) Uani 1 1 d . . . C7 C 0.5119(3) 0.8934(3) 0.42461(14) 0.0271(6) Uani 1 1 d . . . H7 H 0.5863 0.9367 0.4565 0.033 Uiso 1 1 calc R . . C8 C 0.4450(3) 0.7893(3) 0.45517(15) 0.0300(6) Uani 1 1 d . . . H8 H 0.4737 0.7621 0.5072 0.036 Uiso 1 1 calc R . . C9 C 0.3366(3) 0.7258(3) 0.40930(15) 0.0257(6) Uani 1 1 d . . . H9 H 0.2892 0.6558 0.4296 0.031 Uiso 1 1 calc R . . C10 C 0.2981(2) 0.7656(3) 0.33334(13) 0.0214(5) Uani 1 1 d . . . H10 H 0.2243 0.7209 0.3017 0.026 Uiso 1 1 calc R . . C11 C 0.3648(2) 0.8698(3) 0.30182(13) 0.0194(5) Uani 1 1 d . . . C12 C 0.3092(2) 0.9062(3) 0.21855(13) 0.0180(5) Uani 1 1 d . . . C13 C 0.1909(2) 1.0039(3) 0.21367(13) 0.0199(5) Uani 1 1 d . . . H13A H 0.1318 0.9593 0.2419 0.024 Uiso 1 1 calc R . . H13B H 0.2197 1.0975 0.2379 0.024 Uiso 1 1 calc R . . C14 C 0.2094(3) 1.0837(3) 0.08742(14) 0.0254(6) Uani 1 1 d . . . H14A H 0.2399 1.1807 0.1057 0.030 Uiso 1 1 calc R . . H14B H 0.1619 1.0916 0.0333 0.030 Uiso 1 1 calc R . . C15 C 0.3249(2) 0.9843(3) 0.09396(14) 0.0245(6) Uani 1 1 d . . . H15A H 0.2952 0.8878 0.0744 0.029 Uiso 1 1 calc R . . H15B H 0.3833 1.0223 0.0633 0.029 Uiso 1 1 calc R . . C16 C 0.5240(2) 0.9352(3) 0.18627(14) 0.0193(5) Uani 1 1 d . . . C17 C 0.0097(2) 1.1266(3) 0.12959(16) 0.0263(6) Uani 1 1 d . . . H17A H -0.0502 1.0847 0.1573 0.040 Uiso 1 1 calc R . . H17B H -0.0356 1.1415 0.0761 0.040 Uiso 1 1 calc R . . H17C H 0.0416 1.2189 0.1527 0.040 Uiso 1 1 calc R . . C18 C 0.9963(2) 0.6936(3) 0.11669(15) 0.0237(5) Uani 1 1 d . . . C19 C 0.9210(3) 0.5606(3) 0.08249(16) 0.0296(6) Uani 1 1 d . . . H19A H 0.8284 0.5756 0.0815 0.036 Uiso 1 1 calc R . . H19B H 0.9517 0.4780 0.1165 0.036 Uiso 1 1 calc R . . C20 C 0.9317(3) 0.5212(3) 0.00188(15) 0.0271(6) Uani 1 1 d . . . H20A H 0.9036 0.6043 -0.0323 0.033 Uiso 1 1 calc R . . H20B H 0.8722 0.4405 -0.0171 0.033 Uiso 1 1 calc R . . H3A H 0.074(5) 0.920(5) 0.106(3) 0.067(13) Uiso 1 1 d . . . N1 N 0.5659(2) 0.8773(2) 0.12839(12) 0.0243(5) Uani 1 1 d . . . N2 N 0.3937(2) 0.9749(2) 0.17386(11) 0.0202(5) Uani 1 1 d . . . N3 N 0.1209(2) 1.0274(2) 0.13353(11) 0.0204(5) Uani 1 1 d . . . O1 O 1.04036(19) 0.6989(2) 0.18662(11) 0.0317(5) Uani 1 1 d . . . O2 O 1.0076(2) 0.7964(2) 0.07062(11) 0.0304(5) Uani 1 1 d . . . H12 H 0.276(2) 0.812(3) 0.1934(15) 0.011(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 C1 0.0371(15) 0.0204(14) 0.0394(15) 0.0054(11) 0.0211(12) 0.0085(11) C2 0.0285(13) 0.0198(14) 0.0438(16) 0.0120(11) 0.0147(12) 0.0054(10) C3 0.0232(12) 0.0217(14) 0.0335(14) 0.0086(10) 0.0022(10) -0.0043(10) C4 0.0236(12) 0.0121(12) 0.0272(12) 0.0016(9) 0.0069(10) -0.0018(9) C5 0.0290(12) 0.0173(13) 0.0251(13) -0.0035(9) 0.0043(10) -0.0041(10) C6 0.0275(12) 0.0166(13) 0.0206(12) -0.0041(9) 0.0070(9) -0.0014(9) C7 0.0316(13) 0.0298(15) 0.0178(12) -0.0061(10) 0.0015(10) -0.0032(11) C8 0.0420(15) 0.0307(16) 0.0186(12) 0.0012(10) 0.0098(11) 0.0031(12) C9 0.0347(13) 0.0222(14) 0.0225(12) 0.0029(10) 0.0115(10) -0.0027(10) C10 0.0276(12) 0.0197(13) 0.0173(11) -0.0014(9) 0.0062(9) -0.0016(10) C11 0.0275(12) 0.0140(12) 0.0174(11) -0.0015(8) 0.0069(9) 0.0032(9) C12 0.0246(11) 0.0133(12) 0.0164(10) -0.0011(8) 0.0054(9) -0.0009(9) C13 0.0254(12) 0.0183(13) 0.0168(11) -0.0007(8) 0.0065(9) -0.0002(9) C14 0.0295(13) 0.0267(14) 0.0196(12) 0.0065(10) 0.0052(10) 0.0014(10) C15 0.0273(12) 0.0293(15) 0.0183(11) 0.0045(10) 0.0083(10) 0.0019(10) C16 0.0219(11) 0.0146(12) 0.0222(12) 0.0029(9) 0.0071(9) 0.0008(9) C17 0.0257(12) 0.0218(14) 0.0313(14) 0.0024(10) 0.0064(10) 0.0052(10) C18 0.0253(12) 0.0197(14) 0.0262(12) -0.0031(9) 0.0062(10) 0.0044(9) C19 0.0376(14) 0.0214(14) 0.0322(14) -0.0031(11) 0.0128(12) -0.0026(11) C20 0.0330(14) 0.0181(14) 0.0279(13) -0.0064(10) 0.0026(11) 0.0008(10) N1 0.0278(11) 0.0220(12) 0.0257(11) 0.0023(8) 0.0115(9) 0.0024(9) N2 0.0241(10) 0.0207(11) 0.0167(10) 0.0025(8) 0.0066(8) 0.0018(8) N3 0.0240(10) 0.0172(11) 0.0194(10) 0.0006(8) 0.0040(8) 0.0028(8) O1 0.0335(10) 0.0346(12) 0.0247(10) 0.0002(8) 0.0024(8) -0.0011(8) O2 0.0445(11) 0.0194(10) 0.0241(9) -0.0016(7) 0.0016(8) -0.0030(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 N1 1.338(4) . ? C1 C2 1.373(4) . ? C2 C3 1.393(4) . ? C3 C4 1.381(4) . ? C4 C16 1.404(4) . ? C4 C5 1.505(4) . ? C5 C6 1.522(4) . ? C6 C7 1.387(4) . ? C6 C11 1.402(4) . ? C7 C8 1.392(4) . ? C8 C9 1.382(4) . ? C9 C10 1.385(4) . ? C10 C11 1.400(4) . ? C11 C12 1.517(3) . ? C12 N2 1.487(3) . ? C12 C13 1.539(3) . ? C13 N3 1.477(3) . ? C14 N3 1.492(3) . ? C14 C15 1.520(4) . ? C15 N2 1.456(3) . ? C16 N1 1.343(3) . ? C16 N2 1.400(3) . ? C17 N3 1.489(3) . ? C18 O1 1.239(3) . ? C18 O2 1.292(3) . ? C18 C19 1.524(4) . ? C19 C20 1.531(4) . ? C20 C20 1.522(5) 3_765 ? 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 C1 C2 123.6(3) . . ? C1 C2 C3 118.1(3) . . ? C4 C3 C2 120.1(3) . . ? C3 C4 C16 117.4(2) . . ? C3 C4 C5 123.3(2) . . ? C16 C4 C5 119.3(2) . . ? C4 C5 C6 109.1(2) . . ? C7 C6 C11 118.7(2) . . ? C7 C6 C5 120.4(2) . . ? C11 C6 C5 120.7(2) . . ? C8 C7 C6 122.0(2) . . ? C9 C8 C7 119.5(2) . . ? C8 C9 C10 119.2(2) . . ? C9 C10 C11 121.9(2) . . ? C10 C11 C6 118.7(2) . . ? C10 C11 C12 116.2(2) . . ? C6 C11 C12 125.0(2) . . ? N2 C12 C11 119.4(2) . . ? N2 C12 C13 107.8(2) . . ? C11 C12 C13 108.03(19) . . ? N3 C13 C12 110.98(19) . . ? N3 C14 C15 110.4(2) . . ? N2 C15 C14 108.6(2) . . ? N1 C16 C4 122.9(2) . . ? N1 C16 N2 118.7(2) . . ? C4 C16 N2 118.0(2) . . ? O1 C18 O2 123.8(2) . . ? O1 C18 C19 118.7(2) . . ? O2 C18 C19 117.5(2) . . ? C18 C19 C20 115.4(2) . . ? C19 C20 C20 113.1(3) . 3_765 ? C1 N1 C16 117.9(2) . . ? C16 N2 C15 114.8(2) . . ? C16 N2 C12 120.1(2) . . ? C15 N2 C12 109.8(2) . . ? C13 N3 C17 110.36(19) . . ? C13 N3 C14 111.1(2) . . ? C17 N3 C14 110.7(2) . . ? _diffrn_measured_fraction_theta_max 0.900 _diffrn_reflns_theta_full 'ACTA 50' _diffrn_measured_fraction_theta_full 'ACTA 50' _refine_diff_density_max 0.512 _refine_diff_density_min -0.466 _refine_diff_density_rms 0.103 # Attachment '- Mrtz-fumarate hydrate.cif' data_Mrtz-fumarate-hydrate _database_code_depnum_ccdc_archive 'CCDC 797388' #TrackingRef '- Mrtz-fumarate hydrate.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H25 N3 O5' _chemical_formula_weight 399.44 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 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.244(4) _cell_length_b 18.525(3) _cell_length_c 8.9052(13) _cell_angle_alpha 90.00 _cell_angle_beta 102.753(3) _cell_angle_gamma 90.00 _cell_volume 4061.9(10) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4660 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 22.83 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1696 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9759 _exptl_absorpt_correction_T_max 0.9851 _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 20808 _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3977 _reflns_number_gt 3300 _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^)+(0.0839P)^2^+4.0281P] 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 3977 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0932 _refine_ls_R_factor_gt 0.0791 _refine_ls_wR_factor_ref 0.2020 _refine_ls_wR_factor_gt 0.1917 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.134 _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 0.15116(12) 0.19211(17) 0.2961(4) 0.0648(8) Uani 1 1 d . . . H1 H 0.1373 0.2223 0.3614 0.078 Uiso 1 1 calc R . . C2 C 0.11749(12) 0.1421(2) 0.2140(4) 0.0759(9) Uani 1 1 d . . . H2 H 0.0820 0.1369 0.2256 0.091 Uiso 1 1 calc R . . C3 C 0.13747(12) 0.09882(17) 0.1123(4) 0.0693(8) Uani 1 1 d . . . H3 H 0.1150 0.0650 0.0526 0.083 Uiso 1 1 calc R . . C4 C 0.19031(10) 0.10585(13) 0.0997(3) 0.0495(6) Uani 1 1 d . . . C5 C 0.21439(12) 0.06377(15) -0.0122(3) 0.0566(7) Uani 1 1 d . . . H5A H 0.1858 0.0384 -0.0832 0.068 Uiso 1 1 calc R . . H5B H 0.2317 0.0967 -0.0714 0.068 Uiso 1 1 calc R . . C6 C 0.25533(12) 0.01052(14) 0.0693(3) 0.0535(7) Uani 1 1 d . . . C7 C 0.24732(16) -0.06260(15) 0.0380(4) 0.0710(9) Uani 1 1 d . . . H7 H 0.2166 -0.0771 -0.0341 0.085 Uiso 1 1 calc R . . C8 C 0.28266(19) -0.11344(18) 0.1087(4) 0.0837(12) Uani 1 1 d . . . H8 H 0.2764 -0.1620 0.0847 0.100 Uiso 1 1 calc R . . C9 C 0.32816(19) -0.09247(18) 0.2167(4) 0.0844(12) Uani 1 1 d . . . H9 H 0.3533 -0.1268 0.2639 0.101 Uiso 1 1 calc R . . C10 C 0.33629(15) -0.01961(17) 0.2548(3) 0.0715(9) Uani 1 1 d . . . H10 H 0.3661 -0.0058 0.3308 0.086 Uiso 1 1 calc R . . C11 C 0.30022(11) 0.03242(14) 0.1803(3) 0.0510(6) Uani 1 1 d . . . C12 C 0.31699(10) 0.11056(13) 0.2205(3) 0.0441(6) Uani 1 1 d . . . C13 C 0.36341(10) 0.12808(16) 0.1434(3) 0.0538(7) Uani 1 1 d . . . H13A H 0.3915 0.0917 0.1716 0.065 Uiso 1 1 calc R . . H13B H 0.3502 0.1263 0.0326 0.065 Uiso 1 1 calc R . . C14 C 0.34489(12) 0.25636(16) 0.1596(4) 0.0657(8) Uani 1 1 d . . . H14A H 0.3306 0.2616 0.0497 0.079 Uiso 1 1 calc R . . H14B H 0.3607 0.3021 0.1991 0.079 Uiso 1 1 calc R . . C15 C 0.29963(11) 0.23744(15) 0.2365(3) 0.0588(7) Uani 1 1 d . . . H15A H 0.3134 0.2345 0.3469 0.071 Uiso 1 1 calc R . . H15B H 0.2720 0.2747 0.2161 0.071 Uiso 1 1 calc R . . C16 C 0.22238(9) 0.15703(12) 0.1948(3) 0.0432(5) Uani 1 1 d . . . C17 C 0.43210(14) 0.2164(2) 0.1080(4) 0.0889(12) Uani 1 1 d . . . H17A H 0.4178 0.2191 -0.0011 0.133 Uiso 1 1 calc R . . H17B H 0.4590 0.1789 0.1296 0.133 Uiso 1 1 calc R . . H17C H 0.4484 0.2617 0.1444 0.133 Uiso 1 1 calc R . . C18 C 0.03715(14) 0.0861(3) 0.5877(4) 0.0880(12) Uani 1 1 d . . . C19 C 0.01599(12) 0.0120(2) 0.5641(4) 0.0847(11) Uani 1 1 d . . . H19 H 0.0258 -0.0203 0.6454 0.102 Uiso 1 1 calc R . . C20 C 0.04546(15) 0.3171(4) 0.4525(4) 0.1099(19) Uani 1 1 d . . . C21A C 0.0101(3) 0.3393(4) 0.3007(7) 0.0683(17) Uani 0.50 1 d P . 1 H21A H 0.0038 0.3869 0.3255 0.082 Uiso 0.50 1 calc PR . 1 C21B C 0.0093(3) 0.2893(4) 0.2903(6) 0.0553(15) Uani 0.50 1 d P . 2 H21B H 0.0144 0.2398 0.3041 0.066 Uiso 0.50 1 calc PR . 2 H3A H 0.4030(14) 0.2011(18) 0.291(4) 0.084(10) Uiso 1 1 d . . . N1 N 0.20316(9) 0.20047(11) 0.2885(2) 0.0510(5) Uani 1 1 d . . . N2 N 0.27587(8) 0.16817(10) 0.1784(2) 0.0458(5) Uani 1 1 d . . . N3 N 0.38728(9) 0.19993(14) 0.1871(3) 0.0588(6) Uani 1 1 d . . . O1 O 0.06631(14) 0.1039(2) 0.7076(3) 0.1276(12) Uani 1 1 d . . . O2 O 0.02202(10) 0.1300(2) 0.4702(3) 0.1006(9) Uani 1 1 d . . . O3 O 0.05944(10) 0.2595(2) 0.5192(3) 0.0993(9) Uani 1 1 d . . . O4 O 0.05984(17) 0.3740(3) 0.5120(5) 0.1583(19) Uani 1 1 d . . . O5 O 0.4660(2) 0.0155(3) 0.0971(8) 0.227(3) Uani 1 1 d . . . H2A H 0.042(3) 0.194(4) 0.502(7) 0.18(2) Uiso 1 1 d . . . H12 H 0.3299(9) 0.1125(12) 0.330(3) 0.037(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 C1 0.0549(16) 0.0709(19) 0.0698(18) -0.0086(15) 0.0158(14) 0.0100(14) C2 0.0474(16) 0.089(2) 0.095(2) -0.0102(19) 0.0233(16) -0.0038(16) C3 0.0537(17) 0.072(2) 0.080(2) -0.0154(16) 0.0099(15) -0.0189(14) C4 0.0485(14) 0.0468(14) 0.0519(14) -0.0039(11) 0.0084(11) -0.0069(11) C5 0.0618(16) 0.0561(16) 0.0502(14) -0.0138(12) 0.0089(12) -0.0133(13) C6 0.0744(18) 0.0484(14) 0.0452(13) -0.0080(11) 0.0292(13) -0.0079(13) C7 0.110(3) 0.0477(16) 0.0677(19) -0.0106(14) 0.0459(18) -0.0084(16) C8 0.152(4) 0.0490(18) 0.066(2) -0.0003(15) 0.058(2) 0.006(2) C9 0.145(4) 0.0596(19) 0.062(2) 0.0225(16) 0.050(2) 0.043(2) C10 0.099(2) 0.071(2) 0.0505(15) 0.0119(14) 0.0287(16) 0.0275(18) C11 0.0704(17) 0.0472(14) 0.0424(13) 0.0064(11) 0.0273(12) 0.0109(12) C12 0.0463(13) 0.0526(14) 0.0331(12) 0.0035(10) 0.0079(10) 0.0053(11) C13 0.0494(14) 0.0719(18) 0.0397(13) -0.0015(12) 0.0088(11) 0.0019(13) C14 0.0595(17) 0.0623(18) 0.0687(18) 0.0010(14) -0.0002(14) -0.0240(14) C15 0.0511(15) 0.0474(15) 0.0725(18) -0.0071(13) 0.0022(13) -0.0083(12) C16 0.0435(13) 0.0388(12) 0.0451(12) 0.0038(10) 0.0047(10) 0.0013(10) C17 0.069(2) 0.133(3) 0.070(2) -0.009(2) 0.0256(16) -0.038(2) C18 0.0550(19) 0.137(4) 0.065(2) -0.028(2) -0.0011(16) 0.008(2) C19 0.0487(17) 0.136(3) 0.0652(19) -0.026(2) 0.0040(13) 0.0198(19) C20 0.0468(19) 0.234(7) 0.046(2) 0.027(3) 0.0032(15) 0.002(3) C21A 0.076(5) 0.066(4) 0.053(4) -0.003(3) -0.010(3) 0.010(4) C21B 0.055(4) 0.068(4) 0.040(4) -0.004(2) 0.003(3) 0.000(3) N1 0.0498(12) 0.0472(12) 0.0533(12) -0.0041(9) 0.0057(10) 0.0063(9) N2 0.0413(11) 0.0386(11) 0.0545(12) -0.0018(9) 0.0042(9) -0.0039(8) N3 0.0422(12) 0.0933(18) 0.0380(11) -0.0032(11) 0.0027(9) -0.0159(12) O1 0.125(2) 0.151(3) 0.0818(19) -0.0142(18) -0.0317(18) -0.022(2) O2 0.0764(16) 0.151(3) 0.0648(15) -0.0167(16) -0.0042(12) 0.0021(17) O3 0.0740(16) 0.159(3) 0.0555(14) -0.0131(17) -0.0048(12) 0.0103(18) O4 0.134(3) 0.199(4) 0.110(3) 0.053(3) -0.041(2) -0.032(3) O5 0.203(5) 0.218(5) 0.273(7) 0.059(5) 0.080(5) 0.080(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 N1 1.338(4) . ? C1 C2 1.357(4) . ? C2 C3 1.384(5) . ? C3 C4 1.369(4) . ? C4 C16 1.403(3) . ? C4 C5 1.496(4) . ? C5 C6 1.496(4) . ? C6 C7 1.389(4) . ? C6 C11 1.390(4) . ? C7 C8 1.353(5) . ? C8 C9 1.381(6) . ? C9 C10 1.396(5) . ? C10 C11 1.390(4) . ? C11 C12 1.528(4) . ? C12 N2 1.478(3) . ? C12 C13 1.518(3) . ? C13 N3 1.478(4) . ? C14 N3 1.477(4) . ? C14 C15 1.498(4) . ? C15 N2 1.462(3) . ? C16 N1 1.326(3) . ? C16 N2 1.405(3) . ? C17 N3 1.491(4) . ? C18 O1 1.201(4) . ? C18 O2 1.314(5) . ? C18 C19 1.471(6) . ? C19 C19 1.322(6) 5_556 ? C20 O4 1.199(7) . ? C20 O3 1.234(7) . ? C20 C21A 1.504(7) . ? C20 C21B 1.613(7) . ? C21A C21A 0.934(11) 2 ? C21B C21B 0.765(9) 2 ? 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 C1 C2 123.8(3) . . ? C1 C2 C3 118.2(3) . . ? C4 C3 C2 120.1(3) . . ? C3 C4 C16 117.2(2) . . ? C3 C4 C5 123.5(2) . . ? C16 C4 C5 119.3(2) . . ? C6 C5 C4 111.1(2) . . ? C7 C6 C11 119.2(3) . . ? C7 C6 C5 119.4(3) . . ? C11 C6 C5 121.4(2) . . ? C8 C7 C6 122.2(4) . . ? C7 C8 C9 119.3(3) . . ? C8 C9 C10 119.8(3) . . ? C11 C10 C9 120.6(3) . . ? C10 C11 C6 118.9(3) . . ? C10 C11 C12 115.3(3) . . ? C6 C11 C12 125.7(2) . . ? N2 C12 C13 107.5(2) . . ? N2 C12 C11 118.8(2) . . ? C13 C12 C11 107.4(2) . . ? N3 C13 C12 112.6(2) . . ? N3 C14 C15 110.9(2) . . ? N2 C15 C14 109.8(2) . . ? N1 C16 C4 123.2(2) . . ? N1 C16 N2 118.0(2) . . ? C4 C16 N2 118.4(2) . . ? O1 C18 O2 123.4(4) . . ? O1 C18 C19 121.0(4) . . ? O2 C18 C19 115.6(3) . . ? C19 C19 C18 124.8(5) 5_556 . ? O4 C20 O3 121.4(4) . . ? O4 C20 C21A 102.6(6) . . ? O3 C20 C21A 136.0(7) . . ? O4 C20 C21B 137.1(6) . . ? O3 C20 C21B 101.6(6) . . ? C21A C20 C21B 34.5(3) . . ? C21A C21A C20 163.4(6) 2 . ? C21B C21B C20 161.4(4) 2 . ? C16 N1 C1 117.5(2) . . ? C16 N2 C15 114.9(2) . . ? C16 N2 C12 120.32(19) . . ? C15 N2 C12 109.49(19) . . ? C14 N3 C13 110.8(2) . . ? C14 N3 C17 112.0(3) . . ? C13 N3 C17 111.6(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.251 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.042 # Attachment '- mrtz-hcl.cif' data_Mrtz-Hcl-trihydrate _database_code_depnum_ccdc_archive 'CCDC 797389' #TrackingRef '- mrtz-hcl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H27 Cl2 N3 O3' _chemical_formula_weight 392.32 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 '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 8.539(3) _cell_length_b 13.703(4) _cell_length_c 17.468(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.311(5) _cell_angle_gamma 90.00 _cell_volume 1989.1(10) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 8887 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 26.10 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.347 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8971 _exptl_absorpt_correction_T_max 0.9596 _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 20269 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0260 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 26.13 _reflns_number_total 3964 _reflns_number_gt 3321 _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^)+(0.0543P)^2^+0.9787P] 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 3964 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0606 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1266 _refine_ls_wR_factor_gt 0.1206 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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 0.3767(3) 0.94883(18) 0.34688(15) 0.0482(6) Uani 1 1 d . . . H1 H 0.3620 1.0071 0.3716 0.058 Uiso 1 1 calc R . . C2 C 0.2644(3) 0.9175(2) 0.28422(16) 0.0547(7) Uani 1 1 d . . . H2 H 0.1698 0.9525 0.2662 0.066 Uiso 1 1 calc R . . C3 C 0.2926(3) 0.8320(2) 0.24712(15) 0.0512(6) Uani 1 1 d . . . H3 H 0.2164 0.8107 0.2033 0.061 Uiso 1 1 calc R . . C4 C 0.4300(3) 0.77780(17) 0.27325(12) 0.0391(5) Uani 1 1 d . . . C5 C 0.4690(3) 0.68799(18) 0.23235(12) 0.0467(6) Uani 1 1 d . . . H5A H 0.5756 0.6941 0.2222 0.056 Uiso 1 1 calc R . . H5B H 0.3922 0.6806 0.1823 0.056 Uiso 1 1 calc R . . C6 C 0.4628(3) 0.59980(17) 0.28277(12) 0.0389(5) Uani 1 1 d . . . C7 C 0.3474(3) 0.52769(19) 0.25880(15) 0.0499(6) Uani 1 1 d . . . H7 H 0.2764 0.5329 0.2099 0.060 Uiso 1 1 calc R . . C8 C 0.3359(3) 0.44891(19) 0.30590(17) 0.0580(7) Uani 1 1 d . . . H8 H 0.2587 0.4011 0.2885 0.070 Uiso 1 1 calc R . . C9 C 0.4384(3) 0.44098(18) 0.37849(17) 0.0573(7) Uani 1 1 d . . . H9 H 0.4311 0.3878 0.4106 0.069 Uiso 1 1 calc R . . C10 C 0.5526(3) 0.51229(17) 0.40370(14) 0.0469(6) Uani 1 1 d . . . H10 H 0.6219 0.5067 0.4531 0.056 Uiso 1 1 calc R . . C11 C 0.5660(3) 0.59224(16) 0.35690(12) 0.0365(5) Uani 1 1 d . . . C12 C 0.7034(2) 0.66161(15) 0.38908(12) 0.0329(4) Uani 1 1 d . . . C13 C 0.8570(3) 0.62236(16) 0.36947(13) 0.0395(5) Uani 1 1 d . . . H13A H 0.8697 0.5538 0.3835 0.047 Uiso 1 1 calc R . . H13B H 0.8494 0.6282 0.3134 0.047 Uiso 1 1 calc R . . C14 C 0.9787(3) 0.78360(16) 0.39447(15) 0.0450(5) Uani 1 1 d . . . H14A H 0.9773 0.7935 0.3393 0.054 Uiso 1 1 calc R . . H14B H 1.0690 0.8197 0.4255 0.054 Uiso 1 1 calc R . . C15 C 0.8243(2) 0.82156(16) 0.41123(14) 0.0415(5) Uani 1 1 d . . . H15A H 0.8282 0.8157 0.4670 0.050 Uiso 1 1 calc R . . H15B H 0.8114 0.8900 0.3970 0.050 Uiso 1 1 calc R . . C16 C 0.5426(2) 0.81110(15) 0.33981(12) 0.0335(4) Uani 1 1 d . . . C17 C 1.1527(3) 0.6394(2) 0.3991(2) 0.0699(9) Uani 1 1 d . . . H17A H 1.1520 0.6456 0.3443 0.105 Uiso 1 1 calc R . . H17B H 1.1636 0.5718 0.4140 0.105 Uiso 1 1 calc R . . H17C H 1.2416 0.6756 0.4298 0.105 Uiso 1 1 calc R . . Cl1 Cl 0.01706(8) 0.37438(5) 0.41980(4) 0.0570(2) Uani 1 1 d . . . Cl2 Cl 0.27804(8) 0.56389(5) 0.02993(4) 0.0544(2) Uani 1 1 d . . . H12 H 0.718(2) 0.6619(16) 0.4448(14) 0.034(5) Uiso 1 1 d . . . H1A H 0.582(3) 0.9182(18) 0.4142(15) 0.044(7) Uiso 1 1 d . . . H2A H 0.103(5) 0.159(3) 0.342(2) 0.101(15) Uiso 1 1 d . . . H3A H 1.004(3) 0.668(2) 0.4691(17) 0.060(8) Uiso 1 1 d . . . H1B H 0.359(6) 0.204(4) 0.431(3) 0.123(19) Uiso 1 1 d . . . H2B H 0.116(5) 0.251(3) 0.348(2) 0.093(14) Uiso 1 1 d . . . H3B H 0.096(4) 0.021(2) 0.4289(19) 0.066(10) Uiso 1 1 d . . . H1C H 0.525(6) 0.185(3) 0.467(3) 0.132(17) Uiso 1 1 d . . . H3C H -0.052(4) 0.059(2) 0.4113(19) 0.076(11) Uiso 1 1 d . . . N1 N 0.5110(2) 0.89486(14) 0.37343(12) 0.0399(4) Uani 1 1 d . . . N2 N 0.6877(2) 0.76583(12) 0.36610(10) 0.0355(4) Uani 1 1 d . . . N3 N 0.9991(2) 0.67833(14) 0.41362(12) 0.0418(4) Uani 1 1 d . . . O1 O 0.4246(4) 0.2068(2) 0.47118(17) 0.0907(9) Uani 1 1 d . . . O2 O 0.1465(4) 0.2050(2) 0.32798(17) 0.0887(8) Uani 1 1 d . . . O3 O 0.0248(3) 0.04232(17) 0.39253(14) 0.0681(6) 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 0.0436(13) 0.0425(13) 0.0612(15) 0.0121(11) 0.0175(12) 0.0098(10) C2 0.0396(13) 0.0572(16) 0.0652(16) 0.0256(13) 0.0075(12) 0.0099(11) C3 0.0397(13) 0.0633(16) 0.0447(13) 0.0158(12) -0.0022(10) -0.0044(12) C4 0.0380(11) 0.0470(13) 0.0306(10) 0.0100(9) 0.0046(9) -0.0056(9) C5 0.0489(13) 0.0594(15) 0.0290(11) -0.0049(10) 0.0034(10) -0.0090(11) C6 0.0391(12) 0.0438(12) 0.0358(11) -0.0111(9) 0.0125(9) -0.0053(9) C7 0.0454(13) 0.0572(15) 0.0475(13) -0.0206(12) 0.0116(11) -0.0114(11) C8 0.0588(16) 0.0468(15) 0.0755(19) -0.0237(13) 0.0303(14) -0.0198(12) C9 0.0743(18) 0.0379(13) 0.0676(17) -0.0029(12) 0.0325(15) -0.0093(12) C10 0.0544(14) 0.0413(13) 0.0474(13) -0.0006(10) 0.0167(11) -0.0013(11) C11 0.0395(12) 0.0349(11) 0.0376(11) -0.0060(9) 0.0141(9) -0.0025(9) C12 0.0351(11) 0.0343(11) 0.0286(10) -0.0016(8) 0.0062(8) 0.0009(8) C13 0.0432(12) 0.0331(11) 0.0430(12) -0.0030(9) 0.0116(10) 0.0020(9) C14 0.0366(12) 0.0397(12) 0.0573(14) -0.0021(11) 0.0081(10) -0.0047(10) C15 0.0349(11) 0.0332(11) 0.0524(13) -0.0077(10) 0.0015(10) -0.0013(9) C16 0.0336(11) 0.0347(11) 0.0324(10) 0.0053(8) 0.0086(8) -0.0002(8) C17 0.0425(15) 0.0640(18) 0.111(3) -0.0025(17) 0.0330(16) 0.0098(13) Cl1 0.0624(4) 0.0569(4) 0.0454(3) 0.0010(3) -0.0007(3) 0.0029(3) Cl2 0.0518(4) 0.0548(4) 0.0534(4) 0.0077(3) 0.0051(3) -0.0056(3) N1 0.0388(10) 0.0396(10) 0.0403(10) 0.0009(8) 0.0069(8) 0.0039(8) N2 0.0322(9) 0.0322(9) 0.0394(10) -0.0031(7) 0.0029(7) -0.0005(7) N3 0.0321(9) 0.0431(11) 0.0508(12) 0.0000(9) 0.0106(8) 0.0042(8) O1 0.100(2) 0.110(2) 0.0689(16) 0.0241(14) 0.0325(15) 0.0449(17) O2 0.111(2) 0.0768(18) 0.0977(19) 0.0002(15) 0.0632(17) -0.0003(16) O3 0.0568(13) 0.0758(15) 0.0697(14) 0.0100(11) 0.0103(12) 0.0056(11) _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 1.349(4) . ? C1 N1 1.353(3) . ? C2 C3 1.386(4) . ? C3 C4 1.374(3) . ? C4 C16 1.404(3) . ? C4 C5 1.499(3) . ? C5 C6 1.503(3) . ? C6 C7 1.390(3) . ? C6 C11 1.392(3) . ? C7 C8 1.374(4) . ? C8 C9 1.369(4) . ? C9 C10 1.379(4) . ? C10 C11 1.388(3) . ? C11 C12 1.514(3) . ? C12 N2 1.481(3) . ? C12 C13 1.527(3) . ? C13 N3 1.491(3) . ? C14 N3 1.482(3) . ? C14 C15 1.507(3) . ? C15 N2 1.463(3) . ? C16 N1 1.345(3) . ? C16 N2 1.367(3) . ? C17 N3 1.491(3) . ? 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 119.5(2) . . ? C1 C2 C3 118.7(2) . . ? C4 C3 C2 121.9(2) . . ? C3 C4 C16 118.0(2) . . ? C3 C4 C5 123.5(2) . . ? C16 C4 C5 118.47(19) . . ? C4 C5 C6 109.84(18) . . ? C7 C6 C11 118.7(2) . . ? C7 C6 C5 120.9(2) . . ? C11 C6 C5 120.31(19) . . ? C8 C7 C6 121.4(2) . . ? C9 C8 C7 119.9(2) . . ? C8 C9 C10 119.6(2) . . ? C9 C10 C11 121.3(2) . . ? C10 C11 C6 119.1(2) . . ? C10 C11 C12 116.1(2) . . ? C6 C11 C12 124.68(19) . . ? N2 C12 C11 119.40(17) . . ? N2 C12 C13 107.91(17) . . ? C11 C12 C13 109.12(17) . . ? N3 C13 C12 109.96(17) . . ? N3 C14 C15 110.77(19) . . ? N2 C15 C14 109.84(18) . . ? N1 C16 N2 119.88(19) . . ? N1 C16 C4 118.10(19) . . ? N2 C16 C4 121.74(19) . . ? C16 N1 C1 123.8(2) . . ? C16 N2 C15 119.50(17) . . ? C16 N2 C12 123.15(17) . . ? C15 N2 C12 110.25(16) . . ? C14 N3 C17 111.9(2) . . ? C14 N3 C13 110.15(17) . . ? C17 N3 C13 111.8(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.13 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.396 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.047 # Attachment '- mrtz-hemihydrate refinedO.cif' data_Mrtz-hemihyd-refinedO _database_code_depnum_ccdc_archive 'CCDC 797390' #TrackingRef '- mrtz-hemihydrate refinedO.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H20 N3 O0.50' _chemical_formula_weight 274.36 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 9.801(3) _cell_length_b 17.308(5) _cell_length_c 9.009(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.000(4) _cell_angle_gamma 90.00 _cell_volume 1469.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4398 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 25.68 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 588 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9817 _exptl_absorpt_correction_T_max 0.9885 _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 15057 _diffrn_reflns_av_R_equivalents 0.0384 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 26.07 _reflns_number_total 2896 _reflns_number_gt 2143 _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^)+(0.0732P)^2^+0.5622P] 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 2896 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0883 _refine_ls_R_factor_gt 0.0652 _refine_ls_wR_factor_ref 0.1693 _refine_ls_wR_factor_gt 0.1554 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 -0.2832(3) 0.87720(18) 0.3111(3) 0.0625(7) Uani 1 1 d . . . H1 H -0.3413 0.9000 0.3647 0.075 Uiso 1 1 calc R . . C2 C -0.3302(3) 0.81073(18) 0.2296(3) 0.0639(7) Uani 1 1 d . . . H2 H -0.4159 0.7880 0.2308 0.077 Uiso 1 1 calc R . . C3 C -0.2457(2) 0.77891(15) 0.1460(3) 0.0558(6) Uani 1 1 d . . . H3 H -0.2753 0.7344 0.0882 0.067 Uiso 1 1 calc R . . C4 C -0.1183(2) 0.81233(13) 0.1471(2) 0.0430(5) Uani 1 1 d . . . C5 C -0.0245(2) 0.78178(13) 0.0546(2) 0.0462(6) Uani 1 1 d . . . H5A H -0.0001 0.8233 -0.0057 0.055 Uiso 1 1 calc R . . H5B H -0.0749 0.7424 -0.0161 0.055 Uiso 1 1 calc R . . C6 C 0.1090(2) 0.74780(13) 0.1596(2) 0.0405(5) Uani 1 1 d . . . C7 C 0.1375(2) 0.66968(13) 0.1538(3) 0.0481(6) Uani 1 1 d . . . H7 H 0.0748 0.6386 0.0821 0.058 Uiso 1 1 calc R . . C8 C 0.2562(3) 0.63706(14) 0.2513(3) 0.0563(7) Uani 1 1 d . . . H8 H 0.2749 0.5847 0.2440 0.068 Uiso 1 1 calc R . . C9 C 0.3477(3) 0.68249(15) 0.3604(3) 0.0560(7) Uani 1 1 d . . . H9 H 0.4280 0.6608 0.4277 0.067 Uiso 1 1 calc R . . C10 C 0.3198(2) 0.75996(14) 0.3695(3) 0.0490(6) Uani 1 1 d . . . H10 H 0.3815 0.7901 0.4441 0.059 Uiso 1 1 calc R . . C11 C 0.2011(2) 0.79431(12) 0.2693(2) 0.0405(5) Uani 1 1 d . . . C12 C 0.1883(2) 0.88074(13) 0.2818(3) 0.0416(5) Uani 1 1 d . . . C13 C 0.2768(2) 0.92161(14) 0.1903(3) 0.0531(6) Uani 1 1 d . . . H13A H 0.3702 0.8982 0.2134 0.064 Uiso 1 1 calc R . . H13B H 0.2318 0.9156 0.0807 0.064 Uiso 1 1 calc R . . C14 C 0.1520(3) 1.03922(15) 0.2012(3) 0.0660(8) Uani 1 1 d . . . H14A H 0.1059 1.0392 0.0911 0.079 Uiso 1 1 calc R . . H14B H 0.1634 1.0925 0.2356 0.079 Uiso 1 1 calc R . . C15 C 0.0594(3) 0.99818(14) 0.2827(4) 0.0633(7) Uani 1 1 d . . . H15A H 0.1001 1.0022 0.3935 0.076 Uiso 1 1 calc R . . H15B H -0.0339 1.0219 0.2565 0.076 Uiso 1 1 calc R . . C16 C -0.0772(2) 0.87855(13) 0.2390(2) 0.0431(5) Uani 1 1 d . . . C17 C 0.3731(4) 1.0423(2) 0.1362(5) 0.1078(13) Uani 1 1 d . . . H17A H 0.3878 1.0954 0.1667 0.162 Uiso 1 1 calc R . . H17B H 0.3221 1.0394 0.0289 0.162 Uiso 1 1 calc R . . H17C H 0.4633 1.0170 0.1526 0.162 Uiso 1 1 calc R . . H12 H 0.230(2) 0.8929(12) 0.390(3) 0.044(6) Uiso 1 1 d . . . N1 N -0.1590(2) 0.91102(12) 0.3181(2) 0.0544(5) Uani 1 1 d . . . N2 N 0.04665(19) 0.91677(10) 0.2370(2) 0.0484(5) Uani 1 1 d . . . N3 N 0.2907(2) 1.00377(12) 0.2291(3) 0.0633(6) Uani 1 1 d . . . O1 O 0.4989(6) 0.5498(3) 0.0164(6) 0.141(3) Uani 0.529(9) 1 d P . . 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 0.0424(14) 0.087(2) 0.0601(16) 0.0070(15) 0.0172(12) 0.0168(14) C2 0.0365(13) 0.085(2) 0.0674(17) 0.0138(15) 0.0097(12) 0.0013(13) C3 0.0435(13) 0.0593(16) 0.0556(15) 0.0039(12) -0.0012(11) -0.0027(11) C4 0.0380(12) 0.0449(13) 0.0403(12) 0.0057(10) 0.0012(9) 0.0047(9) C5 0.0521(13) 0.0450(13) 0.0389(12) -0.0038(10) 0.0081(10) 0.0004(10) C6 0.0440(12) 0.0435(13) 0.0369(11) 0.0015(9) 0.0163(9) 0.0028(10) C7 0.0528(14) 0.0420(13) 0.0532(14) -0.0028(10) 0.0206(11) -0.0013(10) C8 0.0619(15) 0.0404(13) 0.0710(17) 0.0060(12) 0.0255(14) 0.0121(12) C9 0.0470(13) 0.0569(16) 0.0636(16) 0.0114(12) 0.0142(12) 0.0144(12) C10 0.0402(12) 0.0529(14) 0.0529(14) -0.0004(11) 0.0111(10) 0.0022(10) C11 0.0379(11) 0.0443(12) 0.0412(12) 0.0019(9) 0.0143(9) 0.0015(9) C12 0.0393(12) 0.0424(12) 0.0397(12) -0.0005(10) 0.0053(10) -0.0015(9) C13 0.0448(13) 0.0543(15) 0.0595(15) 0.0083(12) 0.0131(11) -0.0010(11) C14 0.0652(17) 0.0428(14) 0.0777(19) 0.0015(13) -0.0009(14) -0.0034(12) C15 0.0588(16) 0.0426(14) 0.0855(19) -0.0136(13) 0.0150(14) 0.0038(12) C16 0.0387(12) 0.0472(13) 0.0416(12) 0.0036(10) 0.0080(9) 0.0070(10) C17 0.085(2) 0.084(2) 0.157(4) 0.042(2) 0.038(2) -0.0206(19) N1 0.0441(11) 0.0647(14) 0.0545(12) -0.0023(10) 0.0140(9) 0.0131(10) N2 0.0426(11) 0.0388(11) 0.0632(13) -0.0064(9) 0.0137(9) 0.0035(8) N3 0.0517(12) 0.0503(13) 0.0806(15) 0.0127(11) 0.0058(11) -0.0115(10) O1 0.141(5) 0.149(5) 0.106(4) 0.021(4) -0.012(3) 0.030(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 N1 1.336(3) . ? C1 C2 1.374(4) . ? C2 C3 1.378(4) . ? C3 C4 1.374(3) . ? C4 C16 1.406(3) . ? C4 C5 1.497(3) . ? C5 C6 1.507(3) . ? C6 C7 1.385(3) . ? C6 C11 1.396(3) . ? C7 C8 1.371(3) . ? C8 C9 1.379(4) . ? C9 C10 1.375(3) . ? C10 C11 1.394(3) . ? C11 C12 1.508(3) . ? C12 N2 1.473(3) . ? C12 C13 1.524(3) . ? C13 N3 1.462(3) . ? C14 N3 1.449(3) . ? C14 C15 1.495(4) . ? C15 N2 1.464(3) . ? C16 N1 1.335(3) . ? C16 N2 1.387(3) . ? C17 N3 1.473(4) . ? O1 O1 1.751(12) 3_665 ? 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 C1 C2 124.0(2) . . ? C1 C2 C3 117.6(2) . . ? C4 C3 C2 120.6(3) . . ? C3 C4 C16 117.4(2) . . ? C3 C4 C5 122.9(2) . . ? C16 C4 C5 119.7(2) . . ? C4 C5 C6 110.43(17) . . ? C7 C6 C11 119.5(2) . . ? C7 C6 C5 120.4(2) . . ? C11 C6 C5 119.97(19) . . ? C8 C7 C6 121.5(2) . . ? C7 C8 C9 119.5(2) . . ? C10 C9 C8 119.8(2) . . ? C9 C10 C11 121.4(2) . . ? C10 C11 C6 118.3(2) . . ? C10 C11 C12 116.5(2) . . ? C6 C11 C12 125.04(19) . . ? N2 C12 C11 119.40(18) . . ? N2 C12 C13 106.80(18) . . ? C11 C12 C13 110.41(19) . . ? N3 C13 C12 110.6(2) . . ? N3 C14 C15 112.4(2) . . ? N2 C15 C14 109.6(2) . . ? N1 C16 N2 117.6(2) . . ? N1 C16 C4 122.7(2) . . ? N2 C16 C4 119.43(19) . . ? C16 N1 C1 117.6(2) . . ? C16 N2 C15 117.57(19) . . ? C16 N2 C12 123.84(18) . . ? C15 N2 C12 109.24(18) . . ? C14 N3 C13 110.45(19) . . ? C14 N3 C17 110.2(2) . . ? C13 N3 C17 109.5(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.07 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.313 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.041 # Attachment '- Mrtz-maleate.cif' data_Mrtz-maleate _database_code_depnum_ccdc_archive 'CCDC 797391' #TrackingRef '- Mrtz-maleate.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H23 N3 O4' _chemical_formula_weight 381.42 _chemical_absolute_configuration syn 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 'P2(1)2(1)2(1) ' 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' _cell_length_a 8.930(3) _cell_length_b 9.877(3) _cell_length_c 22.497(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1984.4(10) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2613 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 18.76 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9806 _exptl_absorpt_correction_T_max 0.9876 _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 20643 _diffrn_reflns_av_R_equivalents 0.0493 _diffrn_reflns_av_sigmaI/netI 0.0453 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 26.17 _reflns_number_total 3949 _reflns_number_gt 2889 _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^)+(0.0361P)^2^+0.1416P] 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 -0.1(13) _refine_ls_number_reflns 3949 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0688 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.0964 _refine_ls_wR_factor_gt 0.0888 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 0.7146(3) 1.0000(3) 0.34218(11) 0.0740(8) Uani 1 1 d . . . H1 H 0.6273 1.0396 0.3565 0.089 Uiso 1 1 calc R . . C2 C 0.8308(4) 0.9824(3) 0.38070(11) 0.0775(8) Uani 1 1 d . . . H2 H 0.8222 1.0091 0.4202 0.093 Uiso 1 1 calc R . . C3 C 0.9613(3) 0.9244(3) 0.36012(11) 0.0691(7) Uani 1 1 d . . . H3 H 1.0425 0.9130 0.3855 0.083 Uiso 1 1 calc R . . C4 C 0.9707(3) 0.8835(2) 0.30172(9) 0.0543(6) Uani 1 1 d . . . C5 C 1.1057(3) 0.8188(3) 0.27494(10) 0.0658(7) Uani 1 1 d . . . H5A H 1.0765 0.7376 0.2537 0.079 Uiso 1 1 calc R . . H5B H 1.1751 0.7930 0.3061 0.079 Uiso 1 1 calc R . . C6 C 1.1810(3) 0.9161(2) 0.23283(10) 0.0552(6) Uani 1 1 d . . . C7 C 1.3257(3) 0.9607(3) 0.24413(11) 0.0700(7) Uani 1 1 d . . . H7 H 1.3788 0.9227 0.2756 0.084 Uiso 1 1 calc R . . C8 C 1.3928(3) 1.0592(3) 0.21025(13) 0.0767(8) Uani 1 1 d . . . H8 H 1.4904 1.0865 0.2183 0.092 Uiso 1 1 calc R . . C9 C 1.3146(3) 1.1168(3) 0.16445(12) 0.0718(7) Uani 1 1 d . . . H9 H 1.3583 1.1848 0.1417 0.086 Uiso 1 1 calc R . . C10 C 1.1705(3) 1.0739(2) 0.15193(10) 0.0599(6) Uani 1 1 d . . . H10 H 1.1184 1.1133 0.1206 0.072 Uiso 1 1 calc R . . C11 C 1.1022(2) 0.9728(2) 0.18540(9) 0.0492(5) Uani 1 1 d . . . C12 C 0.9474(2) 0.9289(2) 0.16424(9) 0.0467(5) Uani 1 1 d . . . C13 C 0.9692(2) 0.8378(2) 0.11037(9) 0.0524(5) Uani 1 1 d . . . H13A H 1.0283 0.8855 0.0809 0.063 Uiso 1 1 calc R . . H13B H 1.0245 0.7577 0.1222 0.063 Uiso 1 1 calc R . . C14 C 0.7258(3) 0.7329(2) 0.12877(9) 0.0613(6) Uani 1 1 d . . . H14A H 0.7699 0.6490 0.1427 0.074 Uiso 1 1 calc R . . H14B H 0.6293 0.7124 0.1112 0.074 Uiso 1 1 calc R . . C15 C 0.7056(3) 0.8284(3) 0.18009(9) 0.0585(6) Uani 1 1 d . . . H15A H 0.6605 0.9120 0.1663 0.070 Uiso 1 1 calc R . . H15B H 0.6396 0.7882 0.2094 0.070 Uiso 1 1 calc R . . C16 C 0.8462(3) 0.9071(2) 0.26553(9) 0.0528(6) Uani 1 1 d . . . C17 C 0.8484(3) 0.7070(2) 0.03078(9) 0.0696(7) Uani 1 1 d . . . H17A H 0.9097 0.7531 0.0021 0.104 Uiso 1 1 calc R . . H17B H 0.7533 0.6854 0.0133 0.104 Uiso 1 1 calc R . . H17C H 0.8973 0.6251 0.0430 0.104 Uiso 1 1 calc R . . C18 C 0.6097(3) 0.0935(3) 0.05244(10) 0.0538(6) Uani 1 1 d . . . C19 C 0.4916(3) 0.1715(3) 0.02094(10) 0.0615(6) Uani 1 1 d . . . H19 H 0.4202 0.1191 0.0016 0.074 Uiso 1 1 calc R . . C20 C 0.4721(3) 0.3039(3) 0.01613(10) 0.0612(6) Uani 1 1 d . . . H20 H 0.3917 0.3292 -0.0077 0.073 Uiso 1 1 calc R . . C21 C 0.5557(3) 0.4180(3) 0.04200(11) 0.0619(6) Uani 1 1 d . . . H1A H 0.683(3) 0.287(4) 0.0850(11) 0.104(9) Uiso 1 1 d . . . H3A H 0.775(3) 0.871(2) 0.0703(10) 0.067(8) Uiso 1 1 d . . . N1 N 0.7192(2) 0.9631(2) 0.28461(8) 0.0625(5) Uani 1 1 d . . . N2 N 0.85087(19) 0.85679(18) 0.20689(7) 0.0506(4) Uani 1 1 d . . . N3 N 0.8250(2) 0.79619(19) 0.08347(7) 0.0507(5) Uani 1 1 d . . . O1 O 0.69198(18) 0.15229(18) 0.08993(7) 0.0677(4) Uani 1 1 d . . . O2 O 0.6218(2) -0.02713(18) 0.03895(7) 0.0769(5) Uani 1 1 d . . . O3 O 0.6593(2) 0.3943(2) 0.08069(8) 0.0813(5) Uani 1 1 d . . . O4 O 0.5237(2) 0.53209(19) 0.02646(9) 0.0914(6) Uani 1 1 d . . . H12 H 0.896(2) 1.013(2) 0.1516(7) 0.037(5) 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 0.0769(19) 0.089(2) 0.0558(15) -0.0112(14) 0.0134(15) -0.0041(16) C2 0.095(2) 0.092(2) 0.0465(14) -0.0082(13) 0.0048(16) -0.0266(18) C3 0.0751(18) 0.0833(18) 0.0489(14) 0.0077(13) -0.0123(13) -0.0225(16) C4 0.0598(14) 0.0605(14) 0.0425(12) 0.0107(10) -0.0040(11) -0.0071(12) C5 0.0659(16) 0.0714(16) 0.0602(14) 0.0140(13) -0.0158(13) 0.0053(13) C6 0.0495(13) 0.0590(14) 0.0570(13) -0.0031(11) -0.0039(12) 0.0099(12) C7 0.0532(15) 0.0849(18) 0.0718(16) -0.0077(14) -0.0072(13) 0.0083(14) C8 0.0522(15) 0.087(2) 0.0911(19) -0.0220(17) 0.0079(15) -0.0044(15) C9 0.0648(17) 0.0713(17) 0.0791(17) -0.0080(14) 0.0221(15) -0.0118(14) C10 0.0659(16) 0.0581(14) 0.0557(13) -0.0017(11) 0.0096(12) 0.0001(13) C11 0.0488(13) 0.0510(13) 0.0479(12) -0.0042(11) 0.0056(10) 0.0065(10) C12 0.0536(13) 0.0438(12) 0.0427(11) 0.0038(10) -0.0017(10) 0.0047(11) C13 0.0572(14) 0.0529(13) 0.0473(12) -0.0006(10) 0.0005(10) 0.0019(12) C14 0.0642(15) 0.0666(15) 0.0532(13) 0.0012(12) -0.0009(12) -0.0120(13) C15 0.0543(14) 0.0740(16) 0.0471(12) -0.0017(12) 0.0001(11) -0.0057(12) C16 0.0584(14) 0.0578(13) 0.0421(12) 0.0024(10) 0.0044(11) -0.0061(12) C17 0.0896(18) 0.0614(14) 0.0577(13) -0.0149(12) 0.0016(14) -0.0032(14) C18 0.0558(14) 0.0609(16) 0.0448(12) 0.0015(12) 0.0047(11) 0.0058(12) C19 0.0574(14) 0.0670(17) 0.0600(14) -0.0088(13) -0.0140(12) 0.0013(13) C20 0.0600(15) 0.0636(16) 0.0600(14) -0.0019(12) -0.0180(12) 0.0113(13) C21 0.0688(16) 0.0587(15) 0.0582(15) 0.0036(13) 0.0028(13) 0.0014(14) N1 0.0611(13) 0.0788(14) 0.0475(11) -0.0045(10) 0.0051(10) -0.0011(11) N2 0.0478(11) 0.0630(11) 0.0410(9) 0.0002(9) -0.0010(8) -0.0039(9) N3 0.0631(13) 0.0436(10) 0.0455(10) -0.0043(9) -0.0026(10) 0.0031(10) O1 0.0677(10) 0.0720(11) 0.0633(10) 0.0008(9) -0.0208(9) 0.0053(9) O2 0.0975(13) 0.0584(11) 0.0746(11) -0.0065(9) -0.0136(10) 0.0171(9) O3 0.0870(13) 0.0660(12) 0.0909(13) -0.0044(10) -0.0335(12) -0.0061(10) O4 0.1144(15) 0.0570(11) 0.1026(14) 0.0112(11) -0.0125(13) -0.0018(11) _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 N1 1.346(3) . ? C1 C2 1.364(4) . ? C2 C3 1.378(4) . ? C3 C4 1.377(3) . ? C4 C16 1.398(3) . ? C4 C5 1.491(3) . ? C5 C6 1.508(3) . ? C6 C7 1.389(3) . ? C6 C11 1.396(3) . ? C7 C8 1.374(4) . ? C8 C9 1.368(4) . ? C9 C10 1.384(3) . ? C10 C11 1.392(3) . ? C11 C12 1.525(3) . ? C12 N2 1.473(3) . ? C12 C13 1.522(3) . ? C13 N3 1.481(3) . ? C14 N3 1.488(3) . ? C14 C15 1.502(3) . ? C15 N2 1.457(3) . ? C16 N1 1.333(3) . ? C16 N2 1.410(3) . ? C17 N3 1.492(3) . ? C18 O2 1.234(3) . ? C18 O1 1.260(3) . ? C18 C19 1.486(3) . ? C19 C20 1.324(3) . ? C20 C21 1.471(3) . ? C21 O4 1.214(3) . ? C21 O3 1.292(3) . ? 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 C1 C2 123.6(2) . . ? C1 C2 C3 118.9(2) . . ? C4 C3 C2 119.6(2) . . ? C3 C4 C16 117.3(2) . . ? C3 C4 C5 124.1(2) . . ? C16 C4 C5 118.63(19) . . ? C4 C5 C6 109.97(19) . . ? C7 C6 C11 118.8(2) . . ? C7 C6 C5 120.2(2) . . ? C11 C6 C5 120.7(2) . . ? C8 C7 C6 121.9(2) . . ? C9 C8 C7 119.3(2) . . ? C8 C9 C10 120.0(3) . . ? C9 C10 C11 121.1(2) . . ? C10 C11 C6 118.7(2) . . ? C10 C11 C12 115.6(2) . . ? C6 C11 C12 125.6(2) . . ? N2 C12 C13 107.95(17) . . ? N2 C12 C11 117.68(17) . . ? C13 C12 C11 107.49(17) . . ? N3 C13 C12 112.22(17) . . ? N3 C14 C15 109.54(18) . . ? N2 C15 C14 109.39(19) . . ? N1 C16 C4 123.96(19) . . ? N1 C16 N2 118.22(19) . . ? C4 C16 N2 117.5(2) . . ? O2 C18 O1 124.0(2) . . ? O2 C18 C19 116.4(2) . . ? O1 C18 C19 119.6(2) . . ? C20 C19 C18 130.2(2) . . ? C19 C20 C21 131.1(2) . . ? O4 C21 O3 122.0(2) . . ? O4 C21 C20 118.5(2) . . ? O3 C21 C20 119.4(2) . . ? C16 N1 C1 116.6(2) . . ? C16 N2 C15 115.35(17) . . ? C16 N2 C12 117.17(17) . . ? C15 N2 C12 110.13(16) . . ? C13 N3 C14 110.77(16) . . ? C13 N3 C17 111.52(18) . . ? C14 N3 C17 112.33(17) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.17 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.121 _refine_diff_density_min -0.130 _refine_diff_density_rms 0.026 # Attachment '- mrtz-malonate.cif' data_Mrtz-malonate _database_code_depnum_ccdc_archive 'CCDC 797392' #TrackingRef '- mrtz-malonate.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H23 N3 O4' _chemical_formula_weight 369.41 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 Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.3222(16) _cell_length_b 10.7865(17) _cell_length_c 10.8589(17) _cell_angle_alpha 111.053(2) _cell_angle_beta 115.931(2) _cell_angle_gamma 99.711(2) _cell_volume 935.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4335 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 26.06 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9754 _exptl_absorpt_correction_T_max 0.9826 _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 9393 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0363 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 26.08 _reflns_number_total 3686 _reflns_number_gt 2957 _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^)+(0.0483P)^2^+0.3169P] 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 3686 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0715 _refine_ls_R_factor_gt 0.0565 _refine_ls_wR_factor_ref 0.1295 _refine_ls_wR_factor_gt 0.1223 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 -0.3770(2) 0.6894(2) 0.1307(2) 0.0435(5) Uani 1 1 d . . . H1 H -0.4583 0.6491 0.1384 0.052 Uiso 1 1 calc R . . C2 C -0.4131(2) 0.7158(2) 0.0085(2) 0.0480(5) Uani 1 1 d . . . H2 H -0.5164 0.6913 -0.0672 0.058 Uiso 1 1 calc R . . C3 C -0.2917(3) 0.7802(2) 0.0001(2) 0.0464(5) Uani 1 1 d . . . H3 H -0.3129 0.7996 -0.0820 0.056 Uiso 1 1 calc R . . C4 C -0.1393(2) 0.8157(2) 0.1132(2) 0.0371(4) Uani 1 1 d . . . C5 C -0.0008(3) 0.8925(2) 0.1179(3) 0.0458(5) Uani 1 1 d . . . H5A H 0.0728 0.9747 0.2218 0.055 Uiso 1 1 calc R . . H5B H -0.0343 0.9278 0.0434 0.055 Uiso 1 1 calc R . . C6 C 0.0790(2) 0.7932(2) 0.0784(2) 0.0410(5) Uani 1 1 d . . . C7 C 0.0889(3) 0.7617(3) -0.0521(3) 0.0541(6) Uani 1 1 d . . . H7 H 0.0516 0.8068 -0.1110 0.065 Uiso 1 1 calc R . . C8 C 0.1527(3) 0.6650(3) -0.0964(3) 0.0614(7) Uani 1 1 d . . . H8 H 0.1601 0.6465 -0.1830 0.074 Uiso 1 1 calc R . . C9 C 0.2052(3) 0.5962(2) -0.0114(3) 0.0557(6) Uani 1 1 d . . . H9 H 0.2471 0.5299 -0.0412 0.067 Uiso 1 1 calc R . . C10 C 0.1957(2) 0.6254(2) 0.1180(2) 0.0454(5) Uani 1 1 d . . . H10 H 0.2313 0.5781 0.1746 0.055 Uiso 1 1 calc R . . C11 C 0.1339(2) 0.72463(19) 0.1659(2) 0.0362(4) Uani 1 1 d . . . C12 C 0.1436(2) 0.7560(2) 0.3179(2) 0.0350(4) Uani 1 1 d . . . C13 C 0.3110(2) 0.8567(2) 0.4525(2) 0.0393(5) Uani 1 1 d . . . H13A H 0.3823 0.8170 0.4336 0.047 Uiso 1 1 calc R . . H13B H 0.3329 0.9493 0.4561 0.047 Uiso 1 1 calc R . . C14 C 0.2213(2) 0.9253(2) 0.6314(2) 0.0484(5) Uani 1 1 d . . . H14A H 0.2388 1.0217 0.6447 0.058 Uiso 1 1 calc R . . H14B H 0.2342 0.9287 0.7267 0.058 Uiso 1 1 calc R . . C15 C 0.0573(2) 0.8247(2) 0.4952(2) 0.0450(5) Uani 1 1 d . . . H15A H 0.0373 0.7290 0.4843 0.054 Uiso 1 1 calc R . . H15B H -0.0171 0.8585 0.5138 0.054 Uiso 1 1 calc R . . C16 C -0.1149(2) 0.77890(18) 0.2307(2) 0.0324(4) Uani 1 1 d . . . C17 C 0.5010(3) 0.9787(3) 0.7367(3) 0.0594(6) Uani 1 1 d . . . H17A H 0.5187 1.0714 0.7425 0.089 Uiso 1 1 calc R . . H17B H 0.5733 0.9423 0.7186 0.089 Uiso 1 1 calc R . . H17C H 0.5159 0.9876 0.8337 0.089 Uiso 1 1 calc R . . C18 C 0.3240(2) 0.5404(2) 0.5442(2) 0.0430(5) Uani 1 1 d . . . C19 C 0.3610(3) 0.4281(2) 0.5906(2) 0.0445(5) Uani 1 1 d . . . H19A H 0.4697 0.4715 0.6765 0.053 Uiso 1 1 calc R . . H19B H 0.2984 0.4062 0.6311 0.053 Uiso 1 1 calc R . . C20 C 0.3363(2) 0.2880(2) 0.4676(3) 0.0476(5) Uani 1 1 d . . . H3A H 0.328(2) 0.791(3) 0.606(2) 0.051(6) Uiso 1 1 d . . . H4A H 0.290(4) 0.376(4) 0.339(4) 0.105(10) Uiso 1 1 d . . . N1 N -0.23103(18) 0.71810(16) 0.24031(18) 0.0373(4) Uani 1 1 d . . . N2 N 0.03853(18) 0.81920(17) 0.35179(18) 0.0365(4) Uani 1 1 d . . . N3 N 0.33863(19) 0.87757(18) 0.60586(19) 0.0399(4) Uani 1 1 d . . . O1 O 0.3281(2) 0.64859(17) 0.64299(19) 0.0633(5) Uani 1 1 d . . . O2 O 0.2953(2) 0.52151(19) 0.4133(2) 0.0689(5) Uani 1 1 d . . . O3 O 0.3589(2) 0.19244(18) 0.4961(2) 0.0697(5) Uani 1 1 d . . . O4 O 0.2906(2) 0.2748(2) 0.3295(2) 0.0736(5) Uani 1 1 d . . . H12 H 0.124(2) 0.668(2) 0.321(2) 0.029(5) 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 0.0348(11) 0.0408(11) 0.0483(12) 0.0161(9) 0.0226(10) 0.0128(9) C2 0.0371(11) 0.0548(13) 0.0398(12) 0.0159(10) 0.0165(10) 0.0205(10) C3 0.0562(13) 0.0566(13) 0.0393(11) 0.0273(10) 0.0281(11) 0.0340(11) C4 0.0450(11) 0.0368(10) 0.0431(11) 0.0227(9) 0.0286(10) 0.0240(9) C5 0.0559(13) 0.0466(12) 0.0574(13) 0.0353(11) 0.0371(11) 0.0266(10) C6 0.0364(11) 0.0416(11) 0.0449(12) 0.0201(9) 0.0238(10) 0.0119(9) C7 0.0497(13) 0.0687(15) 0.0514(13) 0.0316(12) 0.0315(12) 0.0219(12) C8 0.0509(14) 0.0784(17) 0.0452(13) 0.0167(13) 0.0319(12) 0.0179(13) C9 0.0424(12) 0.0475(13) 0.0567(14) 0.0052(11) 0.0287(11) 0.0142(10) C10 0.0378(11) 0.0385(11) 0.0508(12) 0.0137(10) 0.0239(10) 0.0140(9) C11 0.0303(10) 0.0305(9) 0.0407(11) 0.0116(8) 0.0196(9) 0.0085(8) C12 0.0360(10) 0.0284(9) 0.0445(11) 0.0196(8) 0.0222(9) 0.0154(8) C13 0.0377(11) 0.0354(10) 0.0473(12) 0.0211(9) 0.0225(10) 0.0187(9) C14 0.0516(13) 0.0496(12) 0.0402(11) 0.0172(10) 0.0230(10) 0.0277(11) C15 0.0444(12) 0.0544(13) 0.0421(11) 0.0235(10) 0.0263(10) 0.0239(10) C16 0.0351(10) 0.0267(9) 0.0363(10) 0.0135(8) 0.0202(9) 0.0157(8) C17 0.0436(13) 0.0508(13) 0.0521(14) 0.0130(11) 0.0134(11) 0.0148(11) C18 0.0455(12) 0.0403(11) 0.0464(12) 0.0256(10) 0.0230(10) 0.0186(9) C19 0.0539(13) 0.0417(11) 0.0495(12) 0.0275(10) 0.0307(11) 0.0238(10) C20 0.0461(12) 0.0413(12) 0.0603(14) 0.0248(11) 0.0318(11) 0.0194(10) N1 0.0371(9) 0.0349(8) 0.0445(9) 0.0196(7) 0.0244(8) 0.0165(7) N2 0.0358(9) 0.0429(9) 0.0369(9) 0.0206(7) 0.0217(7) 0.0199(7) N3 0.0398(9) 0.0317(9) 0.0412(9) 0.0159(7) 0.0169(8) 0.0175(7) O1 0.0917(13) 0.0473(9) 0.0618(10) 0.0312(8) 0.0415(10) 0.0398(9) O2 0.1029(14) 0.0664(11) 0.0567(10) 0.0428(9) 0.0429(10) 0.0456(10) O3 0.0883(13) 0.0485(10) 0.0953(13) 0.0411(10) 0.0571(12) 0.0408(9) O4 0.1039(15) 0.0607(11) 0.0516(10) 0.0219(9) 0.0406(11) 0.0390(11) _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 N1 1.338(2) . ? C1 C2 1.363(3) . ? C2 C3 1.383(3) . ? C3 C4 1.378(3) . ? C4 C16 1.402(3) . ? C4 C5 1.496(3) . ? C5 C6 1.511(3) . ? C6 C7 1.388(3) . ? C6 C11 1.395(3) . ? C7 C8 1.379(3) . ? C8 C9 1.373(4) . ? C9 C10 1.376(3) . ? C10 C11 1.394(3) . ? C11 C12 1.514(3) . ? C12 N2 1.482(2) . ? C12 C13 1.523(3) . ? C13 N3 1.483(2) . ? C14 N3 1.486(3) . ? C14 C15 1.506(3) . ? C15 N2 1.461(2) . ? C16 N1 1.331(2) . ? C16 N2 1.401(2) . ? C17 N3 1.485(3) . ? C18 O2 1.247(2) . ? C18 O1 1.248(3) . ? C18 C19 1.514(3) . ? C19 C20 1.501(3) . ? C20 O3 1.208(3) . ? C20 O4 1.303(3) . ? 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 C1 C2 123.69(19) . . ? C1 C2 C3 118.09(19) . . ? C4 C3 C2 120.14(19) . . ? C3 C4 C16 117.29(18) . . ? C3 C4 C5 123.62(18) . . ? C16 C4 C5 119.09(18) . . ? C4 C5 C6 110.93(16) . . ? C7 C6 C11 119.13(19) . . ? C7 C6 C5 120.13(19) . . ? C11 C6 C5 120.60(17) . . ? C8 C7 C6 121.5(2) . . ? C9 C8 C7 119.4(2) . . ? C8 C9 C10 120.0(2) . . ? C9 C10 C11 121.3(2) . . ? C10 C11 C6 118.66(18) . . ? C10 C11 C12 115.68(18) . . ? C6 C11 C12 125.51(17) . . ? N2 C12 C11 119.29(16) . . ? N2 C12 C13 107.60(15) . . ? C11 C12 C13 107.78(15) . . ? N3 C13 C12 111.99(16) . . ? N3 C14 C15 111.26(16) . . ? N2 C15 C14 109.25(17) . . ? N1 C16 N2 117.90(16) . . ? N1 C16 C4 122.89(17) . . ? N2 C16 C4 118.95(16) . . ? O2 C18 O1 124.25(19) . . ? O2 C18 C19 118.77(19) . . ? O1 C18 C19 116.96(18) . . ? C20 C19 C18 118.30(18) . . ? O3 C20 O4 121.7(2) . . ? O3 C20 C19 121.4(2) . . ? O4 C20 C19 116.94(19) . . ? C16 N1 C1 117.82(17) . . ? C16 N2 C15 115.75(15) . . ? C16 N2 C12 120.43(15) . . ? C15 N2 C12 109.17(15) . . ? C13 N3 C17 111.57(17) . . ? C13 N3 C14 110.47(15) . . ? C17 N3 C14 111.79(16) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.08 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.252 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.039 # Attachment '- Mrtz-salicylate.cif' data_Mrtz-salicylate _database_code_depnum_ccdc_archive 'CCDC 797393' #TrackingRef '- Mrtz-salicylate.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H25 N3 O3' _chemical_formula_weight 403.47 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 13.941(8) _cell_length_b 15.599(9) _cell_length_c 9.412(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.499(11) _cell_angle_gamma 90.00 _cell_volume 2019(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3083 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 22.20 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9851 _exptl_absorpt_correction_T_max 0.9921 _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 20342 _diffrn_reflns_av_R_equivalents 0.0468 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 25.93 _reflns_number_total 3901 _reflns_number_gt 3228 _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^)+(0.0955P)^2^+4.9894P] 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 3901 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1209 _refine_ls_R_factor_gt 0.1056 _refine_ls_wR_factor_ref 0.3101 _refine_ls_wR_factor_gt 0.3023 _refine_ls_goodness_of_fit_ref 1.255 _refine_ls_restrained_S_all 1.255 _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 1.1587(4) 0.3778(4) 0.6801(7) 0.0586(16) Uani 1 1 d . . . H1 H 1.1996 0.4039 0.6244 0.070 Uiso 1 1 calc R . . C2 C 1.1890(4) 0.3028(4) 0.7464(7) 0.0623(16) Uani 1 1 d . . . H2 H 1.2474 0.2776 0.7335 0.075 Uiso 1 1 calc R . . C3 C 1.1303(4) 0.2653(4) 0.8332(6) 0.0503(13) Uani 1 1 d . . . H3 H 1.1491 0.2143 0.8810 0.060 Uiso 1 1 calc R . . C4 C 1.0428(3) 0.3040(3) 0.8489(5) 0.0392(11) Uani 1 1 d . . . C5 C 0.9760(4) 0.2683(3) 0.9424(5) 0.0427(12) Uani 1 1 d . . . H5A H 0.9607 0.3124 1.0078 0.051 Uiso 1 1 calc R . . H5B H 1.0078 0.2215 0.9995 0.051 Uiso 1 1 calc R . . C6 C 0.8838(3) 0.2365(3) 0.8525(5) 0.0382(11) Uani 1 1 d . . . C7 C 0.8589(4) 0.1508(3) 0.8547(6) 0.0489(13) Uani 1 1 d . . . H7 H 0.8989 0.1136 0.9148 0.059 Uiso 1 1 calc R . . C8 C 0.7765(4) 0.1191(4) 0.7703(7) 0.0565(15) Uani 1 1 d . . . H8 H 0.7612 0.0612 0.7745 0.068 Uiso 1 1 calc R . . C9 C 0.7172(4) 0.1729(4) 0.6800(6) 0.0541(14) Uani 1 1 d . . . H9 H 0.6610 0.1521 0.6234 0.065 Uiso 1 1 calc R . . C10 C 0.7418(4) 0.2584(3) 0.6742(6) 0.0472(13) Uani 1 1 d . . . H10 H 0.7024 0.2945 0.6110 0.057 Uiso 1 1 calc R . . C11 C 0.8234(3) 0.2919(3) 0.7597(5) 0.0368(10) Uani 1 1 d . . . C12 C 0.8359(3) 0.3887(3) 0.7534(5) 0.0370(11) Uani 1 1 d . . . C13 C 0.7695(4) 0.4294(3) 0.8460(6) 0.0441(12) Uani 1 1 d . . . H13A H 0.7036 0.4089 0.8149 0.053 Uiso 1 1 calc R . . H13B H 0.7897 0.4117 0.9452 0.053 Uiso 1 1 calc R . . C14 C 0.8712(4) 0.5581(3) 0.8675(6) 0.0510(14) Uani 1 1 d . . . H14A H 0.8990 0.5470 0.9672 0.061 Uiso 1 1 calc R . . H14B H 0.8703 0.6196 0.8527 0.061 Uiso 1 1 calc R . . C15 C 0.9329(4) 0.5167(3) 0.7706(7) 0.0534(14) Uani 1 1 d . . . H15A H 0.9061 0.5283 0.6707 0.064 Uiso 1 1 calc R . . H15B H 0.9984 0.5397 0.7902 0.064 Uiso 1 1 calc R . . C16 C 1.0183(3) 0.3799(3) 0.7729(5) 0.0400(11) Uani 1 1 d . . . C17 C 0.7101(5) 0.5619(4) 0.9366(7) 0.0681(18) Uani 1 1 d . . . H17A H 0.7158 0.6232 0.9359 0.102 Uiso 1 1 calc R . . H17B H 0.7317 0.5409 1.0324 0.102 Uiso 1 1 calc R . . H17C H 0.6434 0.5460 0.9058 0.102 Uiso 1 1 calc R . . C18 C 0.5891(3) 0.6031(3) 0.3835(5) 0.0434(12) Uani 1 1 d . . . C19 C 0.5434(4) 0.5617(4) 0.2588(6) 0.0535(14) Uani 1 1 d . . . C20 C 0.4969(4) 0.6094(5) 0.1425(7) 0.0644(17) Uani 1 1 d . . . H20 H 0.4693 0.5819 0.0579 0.077 Uiso 1 1 calc R . . C21 C 0.4917(4) 0.6976(5) 0.1529(7) 0.0627(17) Uani 1 1 d . . . H21 H 0.4594 0.7293 0.0758 0.075 Uiso 1 1 calc R . . C22 C 0.5342(4) 0.7388(4) 0.2765(7) 0.0612(16) Uani 1 1 d . . . H22 H 0.5299 0.7981 0.2836 0.073 Uiso 1 1 calc R . . C23 C 0.5830(4) 0.6919(4) 0.3898(6) 0.0549(14) Uani 1 1 d . . . H23 H 0.6125 0.7203 0.4724 0.066 Uiso 1 1 calc R . . C24 C 0.6425(4) 0.5531(4) 0.5067(6) 0.0480(12) Uani 1 1 d . . . H12 H 0.813(4) 0.407(3) 0.650(6) 0.049(14) Uiso 1 1 d . . . H3A H 0.731(4) 0.550(4) 0.723(7) 0.065(17) Uiso 1 1 d . . . H3B H 0.570(6) 0.451(5) 0.330(9) 0.09(3) Uiso 1 1 d . . . N1 N 1.0742(3) 0.4172(3) 0.6890(5) 0.0524(12) Uani 1 1 d . . . N2 N 0.9349(3) 0.4242(3) 0.7971(5) 0.0431(10) Uani 1 1 d . . . N3 N 0.7703(3) 0.5246(3) 0.8383(5) 0.0438(10) Uani 1 1 d . . . O1 O 0.6915(3) 0.5968(3) 0.6088(4) 0.0627(11) Uani 1 1 d . . . O2 O 0.6381(3) 0.4736(3) 0.5056(5) 0.0712(13) Uani 1 1 d . . . O3 O 0.5457(4) 0.4751(3) 0.2465(6) 0.0814(16) 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 0.045(3) 0.073(4) 0.061(4) -0.019(3) 0.020(3) -0.021(3) C2 0.044(3) 0.072(4) 0.071(4) -0.019(3) 0.013(3) 0.000(3) C3 0.043(3) 0.053(3) 0.053(3) -0.009(3) 0.002(2) 0.001(2) C4 0.040(3) 0.040(3) 0.034(2) -0.008(2) -0.0035(19) -0.002(2) C5 0.046(3) 0.043(3) 0.036(3) 0.006(2) 0.002(2) 0.003(2) C6 0.037(2) 0.044(3) 0.035(2) -0.001(2) 0.010(2) 0.000(2) C7 0.057(3) 0.038(3) 0.052(3) 0.004(2) 0.013(3) 0.003(2) C8 0.069(4) 0.036(3) 0.067(4) -0.006(3) 0.019(3) -0.010(3) C9 0.050(3) 0.050(3) 0.061(3) -0.013(3) 0.008(3) -0.013(3) C10 0.041(3) 0.049(3) 0.049(3) -0.003(2) -0.001(2) -0.004(2) C11 0.034(2) 0.038(3) 0.039(3) -0.004(2) 0.0091(19) -0.0025(19) C12 0.041(3) 0.036(3) 0.033(2) 0.0015(19) 0.0027(19) -0.001(2) C13 0.048(3) 0.039(3) 0.045(3) 0.000(2) 0.008(2) 0.001(2) C14 0.055(3) 0.037(3) 0.054(3) -0.004(2) -0.011(3) 0.000(2) C15 0.048(3) 0.041(3) 0.067(4) 0.007(3) -0.004(3) -0.002(2) C16 0.038(3) 0.040(3) 0.040(3) -0.007(2) 0.000(2) -0.009(2) C17 0.086(5) 0.058(4) 0.060(4) -0.011(3) 0.014(3) 0.019(3) C18 0.033(2) 0.054(3) 0.044(3) 0.003(2) 0.009(2) 0.005(2) C19 0.041(3) 0.060(4) 0.057(3) -0.005(3) 0.001(2) 0.003(3) C20 0.050(3) 0.091(5) 0.047(3) 0.002(3) -0.007(3) 0.003(3) C21 0.048(3) 0.084(5) 0.053(3) 0.023(3) -0.001(3) 0.010(3) C22 0.054(3) 0.064(4) 0.066(4) 0.011(3) 0.012(3) 0.003(3) C23 0.049(3) 0.059(4) 0.055(3) 0.003(3) 0.006(3) 0.002(3) C24 0.041(3) 0.054(3) 0.049(3) 0.005(3) 0.009(2) 0.002(2) N1 0.051(3) 0.057(3) 0.049(3) -0.003(2) 0.008(2) -0.014(2) N2 0.039(2) 0.034(2) 0.054(3) 0.0018(18) 0.0025(19) -0.0043(17) N3 0.054(3) 0.035(2) 0.042(2) -0.0030(18) 0.0043(19) 0.0064(18) O1 0.069(3) 0.062(3) 0.050(2) 0.0071(19) -0.010(2) 0.002(2) O2 0.085(3) 0.051(3) 0.071(3) 0.007(2) -0.008(2) 0.007(2) O3 0.089(4) 0.066(3) 0.079(3) -0.016(3) -0.016(3) 0.014(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.343(8) . ? C1 C2 1.360(9) . ? C2 C3 1.378(9) . ? C3 C4 1.391(7) . ? C4 C16 1.396(7) . ? C4 C5 1.490(7) . ? C5 C6 1.502(7) . ? C6 C7 1.382(7) . ? C6 C11 1.405(7) . ? C7 C8 1.376(8) . ? C8 C9 1.371(8) . ? C9 C10 1.380(8) . ? C10 C11 1.383(7) . ? C11 C12 1.521(7) . ? C12 N2 1.481(6) . ? C12 C13 1.513(7) . ? C13 N3 1.488(6) . ? C14 N3 1.483(7) . ? C14 C15 1.500(8) . ? C15 N2 1.464(6) . ? C16 N1 1.332(7) . ? C16 N2 1.403(6) . ? C17 N3 1.468(7) . ? C18 C23 1.390(8) . ? C18 C19 1.398(7) . ? C18 C24 1.490(7) . ? C19 O3 1.358(8) . ? C19 C20 1.392(8) . ? C20 C21 1.383(9) . ? C21 C22 1.374(9) . ? C22 C23 1.377(8) . ? C24 O2 1.243(7) . ? C24 O1 1.279(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 N1 C1 C2 125.1(5) . . ? C1 C2 C3 117.9(6) . . ? C2 C3 C4 119.7(6) . . ? C3 C4 C16 117.3(5) . . ? C3 C4 C5 123.1(5) . . ? C16 C4 C5 119.7(4) . . ? C4 C5 C6 110.6(4) . . ? C7 C6 C11 118.6(5) . . ? C7 C6 C5 120.3(5) . . ? C11 C6 C5 121.1(4) . . ? C8 C7 C6 121.8(5) . . ? C9 C8 C7 119.8(5) . . ? C8 C9 C10 119.2(5) . . ? C9 C10 C11 121.9(5) . . ? C10 C11 C6 118.7(5) . . ? C10 C11 C12 116.2(4) . . ? C6 C11 C12 125.0(4) . . ? N2 C12 C13 108.3(4) . . ? N2 C12 C11 117.9(4) . . ? C13 C12 C11 108.0(4) . . ? N3 C13 C12 112.4(4) . . ? N3 C14 C15 111.0(4) . . ? N2 C15 C14 108.5(5) . . ? N1 C16 C4 123.9(5) . . ? N1 C16 N2 117.6(5) . . ? C4 C16 N2 118.2(4) . . ? C23 C18 C19 118.2(5) . . ? C23 C18 C24 121.0(5) . . ? C19 C18 C24 120.8(5) . . ? O3 C19 C20 118.6(6) . . ? O3 C19 C18 121.2(5) . . ? C20 C19 C18 120.2(6) . . ? C21 C20 C19 119.9(6) . . ? C22 C21 C20 120.3(6) . . ? C21 C22 C23 119.7(6) . . ? C22 C23 C18 121.6(6) . . ? O2 C24 O1 123.9(5) . . ? O2 C24 C18 119.9(5) . . ? O1 C24 C18 116.2(5) . . ? C16 N1 C1 116.2(5) . . ? C16 N2 C15 116.8(4) . . ? C16 N2 C12 122.0(4) . . ? C15 N2 C12 109.3(4) . . ? C17 N3 C14 111.5(4) . . ? C17 N3 C13 110.8(4) . . ? C14 N3 C13 110.9(4) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.93 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.317 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.069 # Attachment '- mrtz-hemihydrate fixedO.cif' data_Mrtz-hemihyd-fixedO _database_code_depnum_ccdc_archive 'CCDC 806223' #TrackingRef '- mrtz-hemihydrate fixedO.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H20 N3 O0.50' _chemical_formula_weight 274.36 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 9.801(3) _cell_length_b 17.308(5) _cell_length_c 9.009(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.000(4) _cell_angle_gamma 90.00 _cell_volume 1469.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4398 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 25.68 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 588 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9817 _exptl_absorpt_correction_T_max 0.9885 _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 15057 _diffrn_reflns_av_R_equivalents 0.0384 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 26.07 _reflns_number_total 2896 _reflns_number_gt 2143 _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^)+(0.0761P)^2^+0.5597P] 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 2896 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0883 _refine_ls_R_factor_gt 0.0652 _refine_ls_wR_factor_ref 0.1716 _refine_ls_wR_factor_gt 0.1574 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 -0.2832(3) 0.87721(18) 0.3111(3) 0.0625(7) Uani 1 1 d . . . H1 H -0.3413 0.9000 0.3647 0.075 Uiso 1 1 calc R . . C2 C -0.3302(3) 0.81071(18) 0.2296(3) 0.0639(7) Uani 1 1 d . . . H2 H -0.4159 0.7880 0.2308 0.077 Uiso 1 1 calc R . . C3 C -0.2457(2) 0.77891(15) 0.1460(3) 0.0558(6) Uani 1 1 d . . . H3 H -0.2753 0.7344 0.0882 0.067 Uiso 1 1 calc R . . C4 C -0.1183(2) 0.81234(13) 0.1471(2) 0.0430(5) Uani 1 1 d . . . C5 C -0.0245(2) 0.78178(13) 0.0547(2) 0.0462(6) Uani 1 1 d . . . H5A H -0.0001 0.8233 -0.0057 0.055 Uiso 1 1 calc R . . H5B H -0.0749 0.7424 -0.0161 0.055 Uiso 1 1 calc R . . C6 C 0.1090(2) 0.74780(13) 0.1596(2) 0.0405(5) Uani 1 1 d . . . C7 C 0.1375(2) 0.66967(13) 0.1538(3) 0.0481(6) Uani 1 1 d . . . H7 H 0.0748 0.6386 0.0821 0.058 Uiso 1 1 calc R . . C8 C 0.2562(3) 0.63705(14) 0.2513(3) 0.0563(7) Uani 1 1 d . . . H8 H 0.2749 0.5847 0.2440 0.068 Uiso 1 1 calc R . . C9 C 0.3476(3) 0.68249(15) 0.3604(3) 0.0560(7) Uani 1 1 d . . . H9 H 0.4279 0.6608 0.4276 0.067 Uiso 1 1 calc R . . C10 C 0.3198(2) 0.75996(14) 0.3695(3) 0.0490(6) Uani 1 1 d . . . H10 H 0.3815 0.7901 0.4441 0.059 Uiso 1 1 calc R . . C11 C 0.2011(2) 0.79431(12) 0.2693(2) 0.0404(5) Uani 1 1 d . . . C12 C 0.1884(2) 0.88075(13) 0.2818(3) 0.0416(5) Uani 1 1 d . . . C13 C 0.2768(2) 0.92161(14) 0.1903(3) 0.0531(6) Uani 1 1 d . . . H13A H 0.3702 0.8982 0.2134 0.064 Uiso 1 1 calc R . . H13B H 0.2318 0.9156 0.0806 0.064 Uiso 1 1 calc R . . C14 C 0.1520(3) 1.03923(15) 0.2012(3) 0.0660(8) Uani 1 1 d . . . H14A H 0.1059 1.0392 0.0911 0.079 Uiso 1 1 calc R . . H14B H 0.1634 1.0925 0.2356 0.079 Uiso 1 1 calc R . . C15 C 0.0594(3) 0.99817(14) 0.2828(4) 0.0632(7) Uani 1 1 d . . . H15A H 0.1001 1.0022 0.3936 0.076 Uiso 1 1 calc R . . H15B H -0.0339 1.0219 0.2566 0.076 Uiso 1 1 calc R . . C16 C -0.0772(2) 0.87855(13) 0.2390(2) 0.0431(5) Uani 1 1 d . . . C17 C 0.3731(4) 1.0423(2) 0.1364(5) 0.1078(14) Uani 1 1 d . . . H17A H 0.3875 1.0955 0.1668 0.162 Uiso 1 1 calc R . . H17B H 0.3222 1.0393 0.0290 0.162 Uiso 1 1 calc R . . H17C H 0.4634 1.0171 0.1529 0.162 Uiso 1 1 calc R . . H12 H 0.230(2) 0.8931(12) 0.390(3) 0.044(6) Uiso 1 1 d . . . N1 N -0.1590(2) 0.91102(12) 0.3181(2) 0.0544(6) Uani 1 1 d . . . N2 N 0.04666(19) 0.91677(10) 0.2370(2) 0.0484(5) Uani 1 1 d . . . N3 N 0.2907(2) 1.00377(12) 0.2291(3) 0.0633(6) Uani 1 1 d . . . O1 O 0.4989(6) 0.5499(4) 0.0164(6) 0.133(2) Uani 0.50 1 d P . . 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 0.0423(14) 0.087(2) 0.0600(16) 0.0070(15) 0.0172(12) 0.0168(14) C2 0.0365(13) 0.085(2) 0.0675(17) 0.0138(15) 0.0096(12) 0.0014(13) C3 0.0435(13) 0.0593(16) 0.0556(15) 0.0039(12) -0.0011(11) -0.0027(11) C4 0.0380(12) 0.0449(13) 0.0403(12) 0.0058(10) 0.0012(9) 0.0047(9) C5 0.0520(13) 0.0449(13) 0.0389(12) -0.0038(10) 0.0081(10) 0.0004(10) C6 0.0440(12) 0.0435(13) 0.0369(11) 0.0014(9) 0.0163(9) 0.0029(10) C7 0.0528(14) 0.0420(13) 0.0532(14) -0.0028(10) 0.0206(11) -0.0013(10) C8 0.0618(15) 0.0404(13) 0.0709(17) 0.0060(12) 0.0254(14) 0.0121(12) C9 0.0469(14) 0.0569(16) 0.0636(16) 0.0114(12) 0.0142(12) 0.0144(12) C10 0.0401(12) 0.0529(14) 0.0529(14) -0.0004(11) 0.0111(10) 0.0022(10) C11 0.0378(11) 0.0443(13) 0.0412(12) 0.0019(9) 0.0143(9) 0.0014(9) C12 0.0393(12) 0.0423(12) 0.0398(12) -0.0005(10) 0.0053(10) -0.0015(9) C13 0.0447(13) 0.0543(15) 0.0595(15) 0.0084(12) 0.0131(11) -0.0010(11) C14 0.0653(17) 0.0427(14) 0.0777(19) 0.0015(13) -0.0010(14) -0.0034(12) C15 0.0586(16) 0.0427(14) 0.0855(19) -0.0136(13) 0.0150(14) 0.0038(12) C16 0.0387(12) 0.0471(13) 0.0416(12) 0.0036(10) 0.0080(9) 0.0070(10) C17 0.085(2) 0.084(2) 0.157(4) 0.042(2) 0.039(2) -0.0206(19) N1 0.0442(11) 0.0646(14) 0.0546(12) -0.0023(10) 0.0140(9) 0.0131(10) N2 0.0426(11) 0.0387(11) 0.0632(13) -0.0064(9) 0.0137(9) 0.0035(8) N3 0.0516(12) 0.0503(13) 0.0806(15) 0.0127(11) 0.0057(11) -0.0115(10) O1 0.131(4) 0.142(5) 0.099(4) 0.021(4) -0.013(3) 0.028(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 N1 1.336(3) . ? C1 C2 1.375(4) . ? C2 C3 1.378(4) . ? C3 C4 1.374(3) . ? C4 C16 1.406(3) . ? C4 C5 1.497(3) . ? C5 C6 1.507(3) . ? C6 C7 1.385(3) . ? C6 C11 1.396(3) . ? C7 C8 1.372(3) . ? C8 C9 1.379(4) . ? C9 C10 1.375(3) . ? C10 C11 1.394(3) . ? C11 C12 1.508(3) . ? C12 N2 1.474(3) . ? C12 C13 1.525(3) . ? C13 N3 1.462(3) . ? C14 N3 1.449(3) . ? C14 C15 1.495(4) . ? C15 N2 1.463(3) . ? C16 N1 1.335(3) . ? C16 N2 1.386(3) . ? C17 N3 1.472(4) . ? O1 O1 1.752(12) 3_665 ? 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 C1 C2 123.9(2) . . ? C1 C2 C3 117.6(2) . . ? C4 C3 C2 120.6(3) . . ? C3 C4 C16 117.4(2) . . ? C3 C4 C5 122.9(2) . . ? C16 C4 C5 119.7(2) . . ? C4 C5 C6 110.43(17) . . ? C7 C6 C11 119.5(2) . . ? C7 C6 C5 120.4(2) . . ? C11 C6 C5 119.98(19) . . ? C8 C7 C6 121.5(2) . . ? C7 C8 C9 119.4(2) . . ? C10 C9 C8 119.9(2) . . ? C9 C10 C11 121.4(2) . . ? C10 C11 C6 118.3(2) . . ? C10 C11 C12 116.5(2) . . ? C6 C11 C12 125.04(19) . . ? N2 C12 C11 119.39(18) . . ? N2 C12 C13 106.80(18) . . ? C11 C12 C13 110.40(19) . . ? N3 C13 C12 110.6(2) . . ? N3 C14 C15 112.4(2) . . ? N2 C15 C14 109.6(2) . . ? N1 C16 N2 117.6(2) . . ? N1 C16 C4 122.7(2) . . ? N2 C16 C4 119.43(19) . . ? C16 N1 C1 117.7(2) . . ? C16 N2 C15 117.57(19) . . ? C16 N2 C12 123.83(18) . . ? C15 N2 C12 109.24(18) . . ? C14 N3 C13 110.46(19) . . ? C14 N3 C17 110.2(2) . . ? C13 N3 C17 109.5(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.07 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.313 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.041