# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_pkp25 _database_code_depnum_ccdc_archive 'CCDC 903469' #TrackingRef 'Compound-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H22 N2' _chemical_formula_weight 230.35 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 10.0647(7) _cell_length_b 13.9863(12) _cell_length_c 20.4134(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2873.6(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1696 _cell_measurement_theta_min 2.8366 _cell_measurement_theta_max 29.0367 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.065 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.063 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9913 _exptl_absorpt_correction_T_max 0.9931 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8892 _diffrn_reflns_av_R_equivalents 0.0467 _diffrn_reflns_av_sigmaI/netI 0.1092 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 29.10 _reflns_number_total 5847 _reflns_number_gt 2600 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker FRAMBO' _computing_cell_refinement 'Bruker FRAMBO' _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^)+(0.0416P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -3(4) _refine_ls_number_reflns 5847 _refine_ls_number_parameters 327 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1930 _refine_ls_R_factor_gt 0.0813 _refine_ls_wR_factor_ref 0.1605 _refine_ls_wR_factor_gt 0.1213 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 C21 C 0.2856(4) 0.9611(3) 0.18260(19) 0.0520(10) Uani 1 1 d . . . C6 C 0.3635(4) 0.2779(3) 0.1264(2) 0.0572(10) Uani 1 1 d . . . C19 C 0.2026(4) 0.9783(3) 0.0692(2) 0.0550(10) Uani 1 1 d . . . N4 N 0.3799(3) 1.0313(3) 0.18154(19) 0.0583(9) Uani 1 1 d . . . N3 N 0.1067(4) 1.0469(3) 0.0813(2) 0.0672(10) Uani 1 1 d . . . N1 N 0.1411(4) 0.1998(3) 0.2092(2) 0.0707(12) Uani 1 1 d . . . C20 C 0.2445(4) 0.9088(3) 0.12157(18) 0.0538(10) Uani 1 1 d . . . N2 N 0.3432(4) 0.2202(3) 0.07393(19) 0.0675(10) Uani 1 1 d . . . C28 C 0.1264(4) 0.8417(3) 0.1387(2) 0.0697(12) Uani 1 1 d . . . H28A H 0.1561 0.7960 0.1713 0.084 Uiso 1 1 calc R . . H28B H 0.0566 0.8799 0.1585 0.084 Uiso 1 1 calc R . . C25 C 0.3645(4) 0.8513(3) 0.09535(19) 0.0630(11) Uani 1 1 d . . . H25A H 0.3367 0.8185 0.0558 0.076 Uiso 1 1 calc R . . H25B H 0.4333 0.8964 0.0830 0.076 Uiso 1 1 calc R . . C5 C 0.2520(4) 0.3376(3) 0.15468(19) 0.0575(10) Uani 1 1 d . . . C4 C 0.1330(4) 0.2764(3) 0.1689(2) 0.0603(11) Uani 1 1 d . . . C22 C 0.2505(4) 0.9513(3) 0.24711(19) 0.0690(12) Uani 1 1 d . . . H22 H 0.1875 0.9089 0.2636 0.083 Uiso 1 1 calc R . . C24 C 0.4045(4) 1.0655(3) 0.2425(2) 0.0689(12) Uani 1 1 d . . . H24 H 0.4641 1.1137 0.2535 0.083 Uiso 1 1 calc R . . C9 C 0.4580(5) 0.1755(3) 0.0561(2) 0.0745(13) Uani 1 1 d . . . H9 H 0.4680 0.1325 0.0217 0.089 Uiso 1 1 calc R . . C23 C 0.3263(4) 1.0165(3) 0.2842(2) 0.0772(13) Uani 1 1 d . . . H23 H 0.3229 1.0244 0.3294 0.093 Uiso 1 1 calc R . . C8 C 0.5543(5) 0.2049(3) 0.0973(2) 0.0789(14) Uani 1 1 d . . . H8 H 0.6428 0.1858 0.0968 0.095 Uiso 1 1 calc R . . C13 C 0.3016(4) 0.3821(3) 0.2193(2) 0.0719(13) Uani 1 1 d . . . H13A H 0.3292 0.3307 0.2482 0.086 Uiso 1 1 calc R . . H13B H 0.3796 0.4203 0.2098 0.086 Uiso 1 1 calc R . . C26 C 0.4257(4) 0.7779(3) 0.1411(2) 0.0832(14) Uani 1 1 d . . . H26A H 0.4527 0.8091 0.1814 0.100 Uiso 1 1 calc R . . H26B H 0.3596 0.7300 0.1521 0.100 Uiso 1 1 calc R . . C10 C 0.2076(5) 0.4129(3) 0.1037(3) 0.0963(16) Uani 1 1 d . . . H10A H 0.1755 0.3788 0.0655 0.116 Uiso 1 1 calc R . . H10B H 0.1324 0.4472 0.1220 0.116 Uiso 1 1 calc R . . C17 C 0.1619(5) 1.0644(3) -0.0215(2) 0.0942(16) Uani 1 1 d . . . H17 H 0.1667 1.0868 -0.0644 0.113 Uiso 1 1 calc R . . C16 C 0.0823(5) 1.0982(3) 0.0261(3) 0.0857(15) Uani 1 1 d . . . H16 H 0.0214 1.1478 0.0219 0.103 Uiso 1 1 calc R . . C1 C 0.0208(6) 0.1573(4) 0.2185(3) 0.0953(17) Uani 1 1 d . . . H1 H 0.0033 0.1030 0.2434 0.114 Uiso 1 1 calc R . . C14 C 0.2041(4) 0.4435(3) 0.2554(2) 0.0853(15) Uani 1 1 d . . . H14A H 0.1200 0.4098 0.2582 0.102 Uiso 1 1 calc R . . H14B H 0.1894 0.5015 0.2305 0.102 Uiso 1 1 calc R . . C3 C 0.0003(5) 0.2831(4) 0.1526(2) 0.0870(15) Uani 1 1 d . . . H3 H -0.0374 0.3287 0.1251 0.104 Uiso 1 1 calc R . . C18 C 0.2366(5) 0.9889(3) 0.0055(2) 0.0797(14) Uani 1 1 d . . . H18 H 0.2992 0.9524 -0.0168 0.096 Uiso 1 1 calc R . . C7 C 0.4954(4) 0.2703(3) 0.1413(2) 0.0670(12) Uani 1 1 d . . . H7 H 0.5391 0.3027 0.1747 0.080 Uiso 1 1 calc R . . C29 C 0.0673(5) 0.7868(4) 0.0814(2) 0.0972(16) Uani 1 1 d . . . H29A H 0.0367 0.8320 0.0487 0.117 Uiso 1 1 calc R . . H29B H 0.1362 0.7479 0.0616 0.117 Uiso 1 1 calc R . . C11 C 0.3006(6) 0.4816(5) 0.0819(3) 0.143(3) Uani 1 1 d . . . H11A H 0.3831 0.4494 0.0711 0.171 Uiso 1 1 calc R . . H11B H 0.3187 0.5258 0.1174 0.171 Uiso 1 1 calc R . . C2 C -0.0676(5) 0.2093(5) 0.1844(3) 0.108(2) Uani 1 1 d . . . H2 H -0.1586 0.1982 0.1824 0.129 Uiso 1 1 calc R . . C30 C -0.0460(5) 0.7237(4) 0.1009(3) 0.145(3) Uani 1 1 d . . . H30A H -0.0157 0.6773 0.1322 0.218 Uiso 1 1 calc R . . H30B H -0.0800 0.6915 0.0629 0.218 Uiso 1 1 calc R . . H30C H -0.1151 0.7618 0.1202 0.218 Uiso 1 1 calc R . . C27 C 0.5449(5) 0.7296(4) 0.1104(2) 0.114(2) Uani 1 1 d . . . H27A H 0.5166 0.6923 0.0734 0.171 Uiso 1 1 calc R . . H27B H 0.5864 0.6885 0.1420 0.171 Uiso 1 1 calc R . . H27C H 0.6072 0.7772 0.0962 0.171 Uiso 1 1 calc R . . C12 C 0.2527(6) 0.5396(4) 0.0208(3) 0.151(3) Uani 1 1 d . . . H12A H 0.2503 0.4983 -0.0167 0.227 Uiso 1 1 calc R . . H12B H 0.3130 0.5914 0.0128 0.227 Uiso 1 1 calc R . . H12C H 0.1654 0.5645 0.0289 0.227 Uiso 1 1 calc R . . C15 C 0.2482(4) 0.4702(4) 0.3239(2) 0.1118(19) Uani 1 1 d . . . H15A H 0.2661 0.4132 0.3485 0.168 Uiso 1 1 calc R . . H15B H 0.1791 0.5060 0.3451 0.168 Uiso 1 1 calc R . . H15C H 0.3272 0.5085 0.3215 0.168 Uiso 1 1 calc R . . H4A H 0.414(4) 1.056(3) 0.1503(19) 0.069(16) Uiso 1 1 d . . . H2A H 0.264(3) 0.209(2) 0.0554(17) 0.054(12) Uiso 1 1 d . . . H3A H 0.073(4) 1.052(3) 0.121(2) 0.088(17) Uiso 1 1 d . . . H1A H 0.206(4) 0.178(3) 0.222(2) 0.071(18) 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 C21 0.059(2) 0.052(2) 0.045(3) -0.001(2) 0.002(2) 0.002(2) C6 0.067(3) 0.058(3) 0.047(3) 0.006(2) 0.007(2) 0.000(2) C19 0.064(2) 0.053(2) 0.048(3) -0.007(2) -0.010(2) 0.010(2) N4 0.064(2) 0.064(2) 0.048(2) 0.005(2) 0.000(2) -0.0007(19) N3 0.068(2) 0.074(3) 0.059(3) -0.010(2) -0.012(2) 0.011(2) N1 0.060(3) 0.077(3) 0.075(3) -0.012(2) 0.003(3) -0.004(3) C20 0.064(2) 0.060(2) 0.037(2) -0.002(2) 0.000(2) 0.006(2) N2 0.069(3) 0.070(2) 0.064(3) -0.005(2) 0.007(2) 0.004(2) C28 0.075(3) 0.072(3) 0.063(3) -0.011(3) -0.005(2) -0.008(2) C25 0.082(3) 0.060(3) 0.048(3) 0.002(2) -0.001(2) 0.011(2) C5 0.070(2) 0.052(2) 0.050(3) -0.006(2) 0.006(2) 0.011(2) C4 0.056(3) 0.073(3) 0.051(3) -0.010(3) -0.003(2) 0.011(3) C22 0.097(3) 0.065(3) 0.045(3) 0.002(2) 0.006(3) -0.015(3) C24 0.082(3) 0.065(3) 0.060(3) -0.003(3) -0.019(3) -0.007(2) C9 0.090(3) 0.061(3) 0.073(3) 0.006(3) 0.029(3) 0.006(3) C23 0.116(4) 0.072(3) 0.043(3) -0.005(3) -0.011(3) -0.010(3) C8 0.068(3) 0.075(3) 0.094(4) 0.011(3) 0.023(3) 0.012(3) C13 0.064(2) 0.070(3) 0.081(3) -0.013(3) 0.014(3) -0.002(2) C26 0.106(3) 0.079(3) 0.065(3) 0.008(3) -0.008(3) 0.026(3) C10 0.102(4) 0.084(4) 0.103(4) 0.019(3) 0.026(3) 0.031(3) C17 0.154(5) 0.082(4) 0.047(3) -0.003(3) -0.027(3) 0.030(3) C16 0.111(4) 0.071(3) 0.075(4) -0.013(3) -0.044(3) 0.029(3) C1 0.084(4) 0.087(4) 0.115(5) -0.032(4) 0.029(4) -0.028(3) C14 0.085(3) 0.085(3) 0.085(4) -0.017(3) 0.009(3) 0.006(3) C3 0.071(3) 0.103(4) 0.088(4) -0.028(3) -0.018(3) 0.016(3) C18 0.120(4) 0.072(3) 0.047(3) -0.002(3) -0.008(3) 0.028(3) C7 0.065(3) 0.067(3) 0.069(3) 0.008(3) 0.009(3) 0.006(2) C29 0.117(4) 0.100(4) 0.075(4) -0.015(3) -0.025(3) -0.027(3) C11 0.128(5) 0.123(5) 0.178(7) 0.047(5) 0.058(5) 0.041(4) C2 0.061(3) 0.126(5) 0.136(6) -0.058(4) 0.003(4) -0.006(4) C30 0.139(5) 0.176(6) 0.120(5) -0.041(5) -0.011(4) -0.087(5) C27 0.137(4) 0.118(5) 0.087(4) 0.008(3) 0.001(4) 0.071(4) C12 0.222(7) 0.123(5) 0.109(5) 0.064(4) 0.033(5) 0.033(5) C15 0.090(3) 0.131(5) 0.115(5) -0.060(4) 0.003(3) -0.002(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 C21 N4 1.365(5) . ? C21 C22 1.371(4) . ? C21 C20 1.503(5) . ? C6 N2 1.357(5) . ? C6 C7 1.366(5) . ? C6 C5 1.513(5) . ? C19 C18 1.354(5) . ? C19 N3 1.382(5) . ? C19 C20 1.505(5) . ? N4 C24 1.356(5) . ? N4 H4A 0.80(4) . ? N3 C16 1.359(5) . ? N3 H3A 0.88(4) . ? N1 C4 1.353(5) . ? N1 C1 1.362(5) . ? N1 H1A 0.77(4) . ? C20 C25 1.546(5) . ? C20 C28 1.554(5) . ? N2 C9 1.363(5) . ? N2 H2A 0.89(3) . ? C28 C29 1.520(5) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C25 C26 1.519(5) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C5 C4 1.500(5) . ? C5 C13 1.542(5) . ? C5 C10 1.548(5) . ? C4 C3 1.380(5) . ? C22 C23 1.410(5) . ? C22 H22 0.9300 . ? C24 C23 1.346(5) . ? C24 H24 0.9300 . ? C9 C8 1.348(6) . ? C9 H9 0.9300 . ? C23 H23 0.9300 . ? C8 C7 1.412(5) . ? C8 H8 0.9300 . ? C13 C14 1.497(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C26 C27 1.513(5) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C10 C11 1.413(6) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C17 C16 1.345(6) . ? C17 C18 1.409(5) . ? C17 H17 0.9300 . ? C16 H16 0.9300 . ? C1 C2 1.344(7) . ? C1 H1 0.9300 . ? C14 C15 1.513(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C3 C2 1.398(7) . ? C3 H3 0.9300 . ? C18 H18 0.9300 . ? C7 H7 0.9300 . ? C29 C30 1.496(6) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C11 C12 1.563(6) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C2 H2 0.9300 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 C21 C22 105.5(4) . . ? N4 C21 C20 121.9(3) . . ? C22 C21 C20 132.6(4) . . ? N2 C6 C7 106.0(4) . . ? N2 C6 C5 121.2(4) . . ? C7 C6 C5 132.8(4) . . ? C18 C19 N3 105.8(4) . . ? C18 C19 C20 133.0(4) . . ? N3 C19 C20 121.1(4) . . ? C24 N4 C21 111.5(4) . . ? C24 N4 H4A 120(3) . . ? C21 N4 H4A 128(3) . . ? C16 N3 C19 110.1(4) . . ? C16 N3 H3A 130(3) . . ? C19 N3 H3A 120(3) . . ? C4 N1 C1 112.1(5) . . ? C4 N1 H1A 126(3) . . ? C1 N1 H1A 122(3) . . ? C21 C20 C19 110.6(3) . . ? C21 C20 C25 109.0(3) . . ? C19 C20 C25 108.0(3) . . ? C21 C20 C28 108.6(3) . . ? C19 C20 C28 109.5(3) . . ? C25 C20 C28 111.2(3) . . ? C6 N2 C9 110.9(4) . . ? C6 N2 H2A 125(2) . . ? C9 N2 H2A 124(2) . . ? C29 C28 C20 115.6(3) . . ? C29 C28 H28A 108.4 . . ? C20 C28 H28A 108.4 . . ? C29 C28 H28B 108.4 . . ? C20 C28 H28B 108.4 . . ? H28A C28 H28B 107.5 . . ? C26 C25 C20 117.1(3) . . ? C26 C25 H25A 108.0 . . ? C20 C25 H25A 108.0 . . ? C26 C25 H25B 108.0 . . ? C20 C25 H25B 108.0 . . ? H25A C25 H25B 107.3 . . ? C4 C5 C6 110.6(3) . . ? C4 C5 C13 108.8(3) . . ? C6 C5 C13 108.0(3) . . ? C4 C5 C10 106.8(4) . . ? C6 C5 C10 109.5(3) . . ? C13 C5 C10 113.2(4) . . ? N1 C4 C3 105.0(4) . . ? N1 C4 C5 121.4(4) . . ? C3 C4 C5 133.4(5) . . ? C21 C22 C23 108.1(4) . . ? C21 C22 H22 125.9 . . ? C23 C22 H22 125.9 . . ? C23 C24 N4 107.1(4) . . ? C23 C24 H24 126.5 . . ? N4 C24 H24 126.5 . . ? C8 C9 N2 107.6(4) . . ? C8 C9 H9 126.2 . . ? N2 C9 H9 126.2 . . ? C24 C23 C22 107.9(4) . . ? C24 C23 H23 126.1 . . ? C22 C23 H23 126.1 . . ? C9 C8 C7 107.0(4) . . ? C9 C8 H8 126.5 . . ? C7 C8 H8 126.5 . . ? C14 C13 C5 116.1(3) . . ? C14 C13 H13A 108.3 . . ? C5 C13 H13A 108.3 . . ? C14 C13 H13B 108.3 . . ? C5 C13 H13B 108.3 . . ? H13A C13 H13B 107.4 . . ? C27 C26 C25 111.6(4) . . ? C27 C26 H26A 109.3 . . ? C25 C26 H26A 109.3 . . ? C27 C26 H26B 109.3 . . ? C25 C26 H26B 109.3 . . ? H26A C26 H26B 108.0 . . ? C11 C10 C5 118.9(4) . . ? C11 C10 H10A 107.6 . . ? C5 C10 H10A 107.6 . . ? C11 C10 H10B 107.6 . . ? C5 C10 H10B 107.6 . . ? H10A C10 H10B 107.0 . . ? C16 C17 C18 107.4(4) . . ? C16 C17 H17 126.3 . . ? C18 C17 H17 126.3 . . ? C17 C16 N3 107.9(4) . . ? C17 C16 H16 126.1 . . ? N3 C16 H16 126.1 . . ? C2 C1 N1 106.2(5) . . ? C2 C1 H1 126.9 . . ? N1 C1 H1 126.9 . . ? C13 C14 C15 113.9(4) . . ? C13 C14 H14A 108.8 . . ? C15 C14 H14A 108.8 . . ? C13 C14 H14B 108.8 . . ? C15 C14 H14B 108.8 . . ? H14A C14 H14B 107.7 . . ? C4 C3 C2 108.1(5) . . ? C4 C3 H3 126.0 . . ? C2 C3 H3 126.0 . . ? C19 C18 C17 108.8(4) . . ? C19 C18 H18 125.6 . . ? C17 C18 H18 125.6 . . ? C6 C7 C8 108.5(4) . . ? C6 C7 H7 125.7 . . ? C8 C7 H7 125.7 . . ? C30 C29 C28 113.1(4) . . ? C30 C29 H29A 109.0 . . ? C28 C29 H29A 109.0 . . ? C30 C29 H29B 109.0 . . ? C28 C29 H29B 109.0 . . ? H29A C29 H29B 107.8 . . ? C10 C11 C12 113.5(5) . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11B 108.9 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C1 C2 C3 108.5(4) . . ? C1 C2 H2 125.8 . . ? C3 C2 H2 125.8 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.865 _diffrn_reflns_theta_full 29.10 _diffrn_measured_fraction_theta_full 0.865 _refine_diff_density_max 0.276 _refine_diff_density_min -0.152 _refine_diff_density_rms 0.029 data_san-s _database_code_depnum_ccdc_archive 'CCDC 903470' #TrackingRef 'Compound-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H24 N4' _chemical_formula_weight 344.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.531(3) _cell_length_b 18.801(7) _cell_length_c 11.864(5) _cell_angle_alpha 90.00 _cell_angle_beta 108.015(6) _cell_angle_gamma 90.00 _cell_volume 1809.6(12) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 418 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9894 _exptl_absorpt_correction_T_max 0.9916 _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 18206 _diffrn_reflns_av_R_equivalents 0.3971 _diffrn_reflns_av_sigmaI/netI 0.3231 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 26.01 _reflns_number_total 3561 _reflns_number_gt 886 _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^)+(0.0883P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3561 _refine_ls_number_parameters 251 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3165 _refine_ls_R_factor_gt 0.0777 _refine_ls_wR_factor_ref 0.2637 _refine_ls_wR_factor_gt 0.1658 _refine_ls_goodness_of_fit_ref 0.856 _refine_ls_restrained_S_all 0.856 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N4 N 0.5826(7) 0.1456(3) 0.4478(6) 0.0610(18) Uani 1 1 d . . . C36 C 0.4434(8) 0.1253(3) 0.4734(6) 0.0459(17) Uani 1 1 d . . . N1 N -0.0231(6) 0.1840(3) 0.0783(5) 0.0526(16) Uani 1 1 d . . . C37 C 0.3406(7) 0.0788(4) 0.2701(5) 0.0460(17) Uani 1 1 d . . . C28 C -0.0165(7) 0.1424(3) 0.2797(5) 0.0455(17) Uani 1 1 d . . . C31 C 0.2214(7) 0.0371(3) 0.4286(5) 0.0499(18) Uani 1 1 d . . . H31A H 0.2958 -0.0030 0.4388 0.060 Uiso 1 1 calc R . . H31B H 0.2153 0.0502 0.5062 0.060 Uiso 1 1 calc R . . C22 C 0.1638(7) 0.1613(3) 0.3487(5) 0.0483(17) Uani 1 1 d . . . H22A H 0.1649 0.1831 0.4231 0.058 Uiso 1 1 calc R . . H22B H 0.2008 0.1970 0.3037 0.058 Uiso 1 1 calc R . . N3 N 0.4192(8) 0.0158(4) 0.2677(6) 0.0618(18) Uani 1 1 d . . . C32 C 0.2920(7) 0.0998(3) 0.3772(5) 0.0457(17) Uani 1 1 d . . . N2 N -0.2831(8) 0.2075(4) 0.2252(6) 0.070(2) Uani 1 1 d . . . C23 C -0.0648(8) 0.1631(4) -0.0370(6) 0.064(2) Uani 1 1 d . . . H23 H -0.0580 0.1906 -0.1004 0.077 Uiso 1 1 calc R . . C29 C -0.0697(7) 0.0761(3) 0.3348(6) 0.0584(19) Uani 1 1 d . . . H29A H -0.0807 0.0888 0.4113 0.070 Uiso 1 1 calc R . . H29B H -0.1770 0.0607 0.2843 0.070 Uiso 1 1 calc R . . C38 C 0.3455(7) 0.1147(4) 0.1723(6) 0.0562(19) Uani 1 1 d . . . H38 H 0.3017 0.1597 0.1502 0.067 Uiso 1 1 calc R . . C27 C -0.1223(8) 0.2049(4) 0.2876(6) 0.0535(19) Uani 1 1 d . . . C26 C -0.0467(7) 0.1299(4) 0.1483(6) 0.0460(17) Uani 1 1 d . . . C39 C 0.4279(9) 0.0728(5) 0.1086(6) 0.068(2) Uani 1 1 d . . . H39 H 0.4466 0.0847 0.0378 0.082 Uiso 1 1 calc R . . C25 C -0.1074(8) 0.0747(4) 0.0739(6) 0.063(2) Uani 1 1 d . . . H25 H -0.1372 0.0306 0.0964 0.075 Uiso 1 1 calc R . . C33 C 0.7025(9) 0.1651(4) 0.5475(7) 0.067(2) Uani 1 1 d . . . H33 H 0.8077 0.1807 0.5519 0.081 Uiso 1 1 calc R . . C34 C 0.6432(9) 0.1580(4) 0.6378(6) 0.060(2) Uani 1 1 d . . . H34 H 0.7000 0.1675 0.7168 0.072 Uiso 1 1 calc R . . C35 C 0.4780(9) 0.1335(3) 0.5930(6) 0.0579(19) Uani 1 1 d . . . H35 H 0.4068 0.1246 0.6370 0.069 Uiso 1 1 calc R . . C30 C 0.0515(8) 0.0147(3) 0.3511(6) 0.0565(19) Uani 1 1 d . . . H30A H 0.0134 -0.0252 0.3873 0.068 Uiso 1 1 calc R . . H30B H 0.0574 -0.0005 0.2743 0.068 Uiso 1 1 calc R . . C40 C 0.4731(10) 0.0130(5) 0.1708(7) 0.074(2) Uani 1 1 d . . . H40 H 0.5316 -0.0243 0.1514 0.089 Uiso 1 1 calc R . . C24 C -0.1183(9) 0.0947(4) -0.0428(7) 0.070(2) Uani 1 1 d . . . H24 H -0.1548 0.0666 -0.1104 0.084 Uiso 1 1 calc R . . C5 C -0.3544(10) 0.2700(5) 0.2433(8) 0.080(3) Uani 1 1 d . . . H5 H -0.4632 0.2839 0.2074 0.096 Uiso 1 1 calc R . . C7 C -0.0924(9) 0.2672(4) 0.3514(6) 0.066(2) Uani 1 1 d . . . H7 H 0.0081 0.2806 0.4050 0.079 Uiso 1 1 calc R . . C6 C -0.2377(10) 0.3072(4) 0.3226(7) 0.079(2) Uani 1 1 d . . . H6 H -0.2507 0.3517 0.3530 0.094 Uiso 1 1 calc R . . H1 H 0.024(6) 0.227(3) 0.108(5) 0.045(19) Uiso 1 1 d . . . H4 H 0.590(7) 0.144(3) 0.378(5) 0.05(2) Uiso 1 1 d . . . H2 H -0.322(7) 0.179(3) 0.171(5) 0.04(2) Uiso 1 1 d . . . H3 H 0.433(8) -0.019(3) 0.318(6) 0.06(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N4 0.052(4) 0.070(5) 0.053(5) -0.008(4) 0.005(4) 0.002(3) C36 0.040(4) 0.041(4) 0.052(5) 0.004(4) 0.008(4) 0.005(3) N1 0.051(4) 0.047(4) 0.054(4) -0.009(4) 0.009(3) -0.004(3) C37 0.043(4) 0.049(5) 0.043(4) 0.001(4) 0.009(3) -0.002(3) C28 0.041(4) 0.046(4) 0.049(4) -0.002(3) 0.014(3) 0.002(3) C31 0.043(4) 0.050(4) 0.056(4) 0.011(4) 0.014(4) 0.007(3) C22 0.055(4) 0.044(4) 0.047(4) -0.005(3) 0.017(3) -0.003(3) N3 0.075(4) 0.046(4) 0.064(5) 0.005(4) 0.020(4) 0.006(4) C32 0.047(4) 0.039(4) 0.051(4) 0.004(3) 0.014(3) 0.007(3) N2 0.051(4) 0.079(5) 0.068(5) -0.020(4) 0.001(4) 0.005(4) C23 0.070(5) 0.074(6) 0.045(5) 0.007(4) 0.013(4) 0.001(4) C29 0.047(4) 0.065(5) 0.062(5) 0.006(4) 0.016(4) -0.008(4) C38 0.053(4) 0.061(5) 0.052(4) 0.000(4) 0.013(4) 0.000(4) C27 0.047(5) 0.055(5) 0.056(5) -0.004(4) 0.013(4) -0.001(4) C26 0.043(4) 0.041(4) 0.053(5) 0.004(4) 0.012(3) -0.001(3) C39 0.074(5) 0.086(6) 0.049(5) -0.002(5) 0.025(4) -0.002(5) C25 0.082(5) 0.046(5) 0.057(5) -0.004(4) 0.017(4) -0.008(4) C33 0.056(5) 0.071(6) 0.064(6) -0.012(5) 0.003(5) -0.007(4) C34 0.068(5) 0.048(5) 0.050(5) -0.010(4) -0.003(4) 0.014(4) C35 0.076(6) 0.054(5) 0.047(5) 0.006(4) 0.024(4) 0.010(4) C30 0.061(5) 0.046(4) 0.069(5) 0.016(4) 0.029(4) 0.001(4) C40 0.082(6) 0.089(7) 0.060(5) -0.024(5) 0.034(5) -0.005(5) C24 0.085(6) 0.065(6) 0.053(5) -0.011(4) 0.010(4) -0.006(5) C5 0.071(6) 0.083(7) 0.093(7) 0.008(5) 0.036(5) 0.044(5) C7 0.054(5) 0.075(6) 0.064(5) -0.004(5) 0.012(4) 0.015(5) C6 0.072(6) 0.064(6) 0.097(7) -0.014(5) 0.022(5) 0.014(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N4 C33 1.354(8) . ? N4 C36 1.368(8) . ? N4 H4 0.85(5) . ? C36 C35 1.366(8) . ? C36 C32 1.513(8) . ? N1 C23 1.360(8) . ? N1 C26 1.367(8) . ? N1 H1 0.92(6) . ? C37 C38 1.354(8) . ? C37 N3 1.365(8) . ? C37 C32 1.506(8) . ? C28 C27 1.503(8) . ? C28 C26 1.516(8) . ? C28 C29 1.539(8) . ? C28 C22 1.544(7) . ? C31 C30 1.516(8) . ? C31 C32 1.534(8) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C22 C32 1.555(8) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? N3 C40 1.364(8) . ? N3 H3 0.86(6) . ? N2 C27 1.343(8) . ? N2 C5 1.371(9) . ? N2 H2 0.82(5) . ? C23 C24 1.358(9) . ? C23 H23 0.9300 . ? C29 C30 1.522(8) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C38 C39 1.418(8) . ? C38 H38 0.9300 . ? C27 C7 1.376(9) . ? C26 C25 1.357(8) . ? C39 C40 1.335(9) . ? C39 H39 0.9300 . ? C25 C24 1.410(8) . ? C25 H25 0.9300 . ? C33 C34 1.324(9) . ? C33 H33 0.9300 . ? C34 C35 1.421(9) . ? C34 H34 0.9300 . ? C35 H35 0.9300 . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C40 H40 0.9300 . ? C24 H24 0.9300 . ? C5 C6 1.337(9) . ? C5 H5 0.9300 . ? C7 C6 1.399(9) . ? C7 H7 0.9300 . ? C6 H6 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C33 N4 C36 110.7(6) . . ? C33 N4 H4 127(4) . . ? C36 N4 H4 123(4) . . ? C35 C36 N4 106.0(6) . . ? C35 C36 C32 132.8(7) . . ? N4 C36 C32 121.2(6) . . ? C23 N1 C26 110.8(6) . . ? C23 N1 H1 126(4) . . ? C26 N1 H1 123(4) . . ? C38 C37 N3 105.6(6) . . ? C38 C37 C32 133.0(6) . . ? N3 C37 C32 120.7(6) . . ? C27 C28 C26 105.7(5) . . ? C27 C28 C29 110.1(5) . . ? C26 C28 C29 109.5(5) . . ? C27 C28 C22 107.8(5) . . ? C26 C28 C22 113.9(5) . . ? C29 C28 C22 109.7(5) . . ? C30 C31 C32 113.0(5) . . ? C30 C31 H31A 109.0 . . ? C32 C31 H31A 109.0 . . ? C30 C31 H31B 109.0 . . ? C32 C31 H31B 109.0 . . ? H31A C31 H31B 107.8 . . ? C28 C22 C32 117.5(5) . . ? C28 C22 H22A 107.9 . . ? C32 C22 H22A 107.9 . . ? C28 C22 H22B 107.9 . . ? C32 C22 H22B 107.9 . . ? H22A C22 H22B 107.2 . . ? C40 N3 C37 110.3(7) . . ? C40 N3 H3 122(4) . . ? C37 N3 H3 127(4) . . ? C37 C32 C36 109.1(5) . . ? C37 C32 C31 112.2(5) . . ? C36 C32 C31 107.0(5) . . ? C37 C32 C22 111.7(5) . . ? C36 C32 C22 107.9(5) . . ? C31 C32 C22 108.7(5) . . ? C27 N2 C5 111.9(7) . . ? C27 N2 H2 121(4) . . ? C5 N2 H2 126(4) . . ? C24 C23 N1 107.7(7) . . ? C24 C23 H23 126.1 . . ? N1 C23 H23 126.1 . . ? C30 C29 C28 112.9(5) . . ? C30 C29 H29A 109.0 . . ? C28 C29 H29A 109.0 . . ? C30 C29 H29B 109.0 . . ? C28 C29 H29B 109.0 . . ? H29A C29 H29B 107.8 . . ? C37 C38 C39 109.4(7) . . ? C37 C38 H38 125.3 . . ? C39 C38 H38 125.3 . . ? N2 C27 C7 104.8(6) . . ? N2 C27 C28 121.7(7) . . ? C7 C27 C28 133.5(6) . . ? C25 C26 N1 105.7(6) . . ? C25 C26 C28 134.1(7) . . ? N1 C26 C28 120.0(6) . . ? C40 C39 C38 106.2(7) . . ? C40 C39 H39 126.9 . . ? C38 C39 H39 126.9 . . ? C26 C25 C24 109.3(7) . . ? C26 C25 H25 125.3 . . ? C24 C25 H25 125.3 . . ? C34 C33 N4 107.8(7) . . ? C34 C33 H33 126.1 . . ? N4 C33 H33 126.1 . . ? C33 C34 C35 108.2(6) . . ? C33 C34 H34 125.9 . . ? C35 C34 H34 125.9 . . ? C36 C35 C34 107.2(6) . . ? C36 C35 H35 126.4 . . ? C34 C35 H35 126.4 . . ? C31 C30 C29 110.5(5) . . ? C31 C30 H30A 109.5 . . ? C29 C30 H30A 109.5 . . ? C31 C30 H30B 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 108.1 . . ? C39 C40 N3 108.6(7) . . ? C39 C40 H40 125.7 . . ? N3 C40 H40 125.7 . . ? C23 C24 C25 106.4(7) . . ? C23 C24 H24 126.8 . . ? C25 C24 H24 126.8 . . ? C6 C5 N2 106.8(7) . . ? C6 C5 H5 126.6 . . ? N2 C5 H5 126.6 . . ? C27 C7 C6 108.9(7) . . ? C27 C7 H7 125.6 . . ? C6 C7 H7 125.6 . . ? C5 C6 C7 107.6(7) . . ? C5 C6 H6 126.2 . . ? C7 C6 H6 126.2 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.220 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.058 data_sanjib_s _database_code_depnum_ccdc_archive 'CCDC 903471' #TrackingRef 'Compound-3 (polymorph-1).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 N2 O' _chemical_formula_weight 228.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pbca ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 12.9488(7) _cell_length_b 14.6721(12) _cell_length_c 25.565(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4857.0(6) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1425 _cell_measurement_theta_min 2.6339 _cell_measurement_theta_max 26.3143 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1952 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9897 _exptl_absorpt_correction_T_max 0.9928 _exptl_absorpt_process_details 'SCALE3 ABSPACK' _exptl_special_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '\w scans' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12737 _diffrn_reflns_av_R_equivalents 0.1793 _diffrn_reflns_av_sigmaI/netI 0.2812 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 26.39 _reflns_number_total 4929 _reflns_number_gt 1358 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrysAlisPro _computing_cell_refinement CrysAlisPro _computing_data_reduction CrysAlisPro _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics '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^)+(0.0159P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4929 _refine_ls_number_parameters 323 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2501 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.0834 _refine_ls_wR_factor_gt 0.0597 _refine_ls_goodness_of_fit_ref 0.709 _refine_ls_restrained_S_all 0.709 _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 O1 O -0.14103(15) 0.11688(14) 0.53473(9) 0.0556(8) Uani 1 1 d . . . C11 C 0.0398(2) 0.10418(19) 0.55170(12) 0.0384(10) Uani 1 1 d . . . H11A H 0.0364 0.0537 0.5272 0.046 Uiso 1 1 calc R . . H11B H 0.0564 0.0794 0.5859 0.046 Uiso 1 1 calc R . . C4 C 0.1076(2) 0.1979(2) 0.47891(14) 0.0306(9) Uani 1 1 d . . . C6 C 0.2318(2) 0.1226(2) 0.53930(13) 0.0325(9) Uani 1 1 d . . . N1 N 0.1649(2) 0.2645(2) 0.45479(15) 0.0445(10) Uani 1 1 d . . . C3 C 0.0387(2) 0.1694(2) 0.44257(15) 0.0417(10) Uani 1 1 d . . . H3 H -0.0108 0.1243 0.4474 0.050 Uiso 1 1 calc R . . C12 C 0.0221(2) 0.3017(2) 0.57029(14) 0.0507(11) Uani 1 1 d . . . H12A H 0.0233 0.3521 0.5948 0.061 Uiso 1 1 calc R . . H12B H 0.0103 0.3264 0.5356 0.061 Uiso 1 1 calc R . . N2 N 0.2492(2) 0.0415(2) 0.51509(13) 0.0458(10) Uani 1 1 d . . . C9 C 0.3501(3) 0.0147(3) 0.52271(15) 0.0540(12) Uani 1 1 d . . . H9 H 0.3812 -0.0380 0.5101 0.065 Uiso 1 1 calc R . . C5 C 0.1276(2) 0.1696(2) 0.53457(14) 0.0308(9) Uani 1 1 d . . . C7 C 0.3216(2) 0.1480(2) 0.56265(14) 0.0477(11) Uani 1 1 d . . . H7 H 0.3325 0.2007 0.5821 0.057 Uiso 1 1 calc R . . C10 C 0.1261(2) 0.2529(2) 0.57143(12) 0.0413(10) Uani 1 1 d . . . H10A H 0.1407 0.2330 0.6069 0.050 Uiso 1 1 calc R . . H10B H 0.1800 0.2951 0.5610 0.050 Uiso 1 1 calc R . . C8 C 0.3947(2) 0.0799(3) 0.55200(15) 0.0532(12) Uani 1 1 d . . . H8 H 0.4630 0.0799 0.5634 0.064 Uiso 1 1 calc R . . C14 C -0.0646(3) 0.1496(2) 0.55432(14) 0.0406(10) Uani 1 1 d . . . C1 C 0.1330(3) 0.2784(3) 0.40516(16) 0.0543(12) Uani 1 1 d . . . H1 H 0.1599 0.3204 0.3816 0.065 Uiso 1 1 calc R . . C2 C 0.0547(3) 0.2196(3) 0.39623(15) 0.0554(11) Uani 1 1 d . . . H2 H 0.0180 0.2134 0.3652 0.067 Uiso 1 1 calc R . . C13 C -0.0658(2) 0.2371(2) 0.58446(14) 0.0590(12) Uani 1 1 d . . . H13A H -0.0619 0.2233 0.6215 0.071 Uiso 1 1 calc R . . H13B H -0.1310 0.2678 0.5782 0.071 Uiso 1 1 calc R . . N3 N 0.1805(3) 1.0110(2) 0.32318(14) 0.0463(10) Uani 1 1 d . . . C28 C 0.1375(2) 1.0096(2) 0.20700(12) 0.0378(10) Uani 1 1 d . . . H28A H 0.1114 0.9823 0.1751 0.045 Uiso 1 1 calc R . . H28B H 0.0789 1.0237 0.2292 0.045 Uiso 1 1 calc R . . O2 O 0.44931(17) 1.01011(17) 0.17749(9) 0.0763(9) Uani 1 1 d . . . C17 C 0.3420(2) 0.9787(2) 0.30849(15) 0.0411(10) Uani 1 1 d . . . H17 H 0.4028 0.9594 0.2926 0.049 Uiso 1 1 calc R . . C18 C 0.2460(3) 0.9765(2) 0.28667(14) 0.0314(9) Uani 1 1 d . . . C24 C 0.3013(2) 0.9206(2) 0.19845(13) 0.0455(10) Uani 1 1 d . . . H24A H 0.3505 0.8827 0.2170 0.055 Uiso 1 1 calc R . . H24B H 0.2769 0.8863 0.1685 0.055 Uiso 1 1 calc R . . C25 C 0.3558(3) 1.0048(3) 0.17921(14) 0.0500(11) Uani 1 1 d . . . C16 C 0.3333(3) 1.0154(2) 0.35943(16) 0.0488(11) Uani 1 1 d . . . H16 H 0.3870 1.0249 0.3830 0.059 Uiso 1 1 calc R . . C27 C 0.1943(2) 1.0974(2) 0.19365(13) 0.0498(11) Uani 1 1 d . . . H27A H 0.2176 1.1265 0.2256 0.060 Uiso 1 1 calc R . . H27B H 0.1475 1.1389 0.1761 0.060 Uiso 1 1 calc R . . N4 N 0.1818(3) 0.7915(3) 0.28086(15) 0.0599(10) Uani 1 1 d . . . C19 C 0.2078(2) 0.9404(2) 0.23530(15) 0.0332(9) Uani 1 1 d . . . C15 C 0.2329(3) 1.0341(2) 0.36751(15) 0.0508(11) Uani 1 1 d . . . H15 H 0.2044 1.0583 0.3979 0.061 Uiso 1 1 calc R . . C26 C 0.2874(2) 1.0784(2) 0.15826(14) 0.0623(13) Uani 1 1 d . . . H26A H 0.2629 1.0607 0.1239 0.075 Uiso 1 1 calc R . . H26B H 0.3274 1.1339 0.1544 0.075 Uiso 1 1 calc R . . C20 C 0.1494(3) 0.8526(2) 0.24413(15) 0.0388(10) Uani 1 1 d . . . C21 C 0.0651(3) 0.8158(2) 0.22067(15) 0.0570(12) Uani 1 1 d . . . H21 H 0.0268 0.8420 0.1938 0.068 Uiso 1 1 calc R . . C22 C 0.0459(3) 0.7305(3) 0.24439(18) 0.0729(14) Uani 1 1 d . . . H22 H -0.0076 0.6908 0.2360 0.088 Uiso 1 1 calc R . . C23 C 0.1177(4) 0.7169(3) 0.28073(17) 0.0760(15) Uani 1 1 d . . . H23 H 0.1235 0.6660 0.3022 0.091 Uiso 1 1 calc R . . H2A H 0.2095(17) 0.0103(17) 0.4962(10) 0.015(10) Uiso 1 1 d . . . H1A H 0.2082(16) 0.2869(17) 0.4699(11) 0.003(10) Uiso 1 1 d . . . H3A H 0.1218(18) 1.0155(19) 0.3206(12) 0.027(11) Uiso 1 1 d . . . H4A H 0.234(3) 0.793(3) 0.302(2) 0.18(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0333(13) 0.0581(19) 0.075(2) -0.0115(15) -0.0008(14) -0.0100(13) C11 0.041(2) 0.036(2) 0.039(3) 0.006(2) 0.000(2) 0.0015(19) C4 0.029(2) 0.024(2) 0.039(3) 0.002(2) 0.005(2) -0.0024(17) C6 0.035(2) 0.035(2) 0.028(3) 0.003(2) -0.0030(19) 0.0046(19) N1 0.039(2) 0.046(2) 0.048(3) 0.000(2) -0.001(2) -0.0058(19) C3 0.036(2) 0.047(3) 0.042(3) 0.004(2) -0.004(2) -0.0066(19) C12 0.052(2) 0.038(2) 0.063(3) -0.028(2) -0.009(2) 0.004(2) N2 0.038(2) 0.042(2) 0.057(3) -0.012(2) -0.0084(19) 0.0009(19) C9 0.039(2) 0.054(3) 0.069(4) 0.009(3) 0.008(2) 0.016(2) C5 0.0240(18) 0.029(2) 0.040(3) -0.001(2) -0.0023(19) 0.0003(17) C7 0.032(2) 0.054(3) 0.057(3) -0.006(2) -0.011(2) 0.004(2) C10 0.035(2) 0.045(2) 0.043(3) -0.006(2) -0.0038(19) 0.0035(19) C8 0.033(2) 0.062(3) 0.064(3) 0.005(3) -0.010(2) 0.006(2) C14 0.044(2) 0.036(2) 0.042(3) 0.004(2) 0.012(2) -0.003(2) C1 0.065(3) 0.061(3) 0.037(3) 0.014(3) 0.015(3) 0.022(2) C2 0.061(3) 0.072(3) 0.034(3) 0.009(3) -0.008(3) 0.015(2) C13 0.039(2) 0.064(3) 0.075(3) -0.024(3) 0.008(2) 0.001(2) N3 0.032(2) 0.061(2) 0.046(3) -0.010(2) 0.000(2) 0.012(2) C28 0.0336(19) 0.047(2) 0.033(2) 0.001(2) -0.0011(18) -0.0035(19) O2 0.0327(14) 0.119(2) 0.077(2) -0.0040(18) 0.0152(15) -0.0034(16) C17 0.027(2) 0.046(3) 0.050(3) 0.003(2) -0.002(2) 0.0046(18) C18 0.034(2) 0.029(2) 0.031(2) 0.002(2) -0.001(2) 0.0047(19) C24 0.041(2) 0.060(3) 0.036(3) -0.006(2) 0.000(2) 0.010(2) C25 0.049(2) 0.071(3) 0.029(3) -0.006(2) 0.009(2) 0.005(3) C16 0.044(2) 0.054(3) 0.048(3) 0.001(2) -0.012(2) -0.004(2) C27 0.044(2) 0.054(3) 0.052(3) 0.016(2) -0.011(2) 0.003(2) N4 0.083(3) 0.047(3) 0.050(3) 0.006(2) -0.004(2) 0.002(2) C19 0.026(2) 0.038(2) 0.035(3) 0.000(2) 0.001(2) 0.0052(19) C15 0.075(3) 0.047(3) 0.030(3) -0.006(2) -0.007(3) 0.001(2) C26 0.049(2) 0.082(3) 0.056(3) 0.025(3) -0.003(2) -0.017(2) C20 0.039(2) 0.036(2) 0.042(3) 0.001(2) 0.000(2) 0.006(2) C21 0.057(3) 0.044(3) 0.070(4) 0.000(3) -0.013(3) -0.009(2) C22 0.089(3) 0.054(3) 0.076(4) -0.015(3) 0.014(3) -0.028(3) C23 0.133(4) 0.035(3) 0.060(4) -0.004(3) 0.015(3) -0.016(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 O1 C14 1.209(3) . ? C11 C14 1.510(3) . ? C11 C5 1.550(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C4 C3 1.354(4) . ? C4 N1 1.373(4) . ? C4 C5 1.505(4) . ? C6 C7 1.359(4) . ? C6 N2 1.360(4) . ? C6 C5 1.520(4) . ? N1 C1 1.350(4) . ? N1 H1A 0.76(2) . ? C3 C2 1.410(4) . ? C3 H3 0.9300 . ? C12 C13 1.525(4) . ? C12 C10 1.525(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? N2 C9 1.378(3) . ? N2 H2A 0.84(2) . ? C9 C8 1.345(4) . ? C9 H9 0.9300 . ? C5 C10 1.543(4) . ? C7 C8 1.403(4) . ? C7 H7 0.9300 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C8 H8 0.9300 . ? C14 C13 1.497(4) . ? C1 C2 1.351(4) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? N3 C18 1.358(4) . ? N3 C15 1.363(4) . ? N3 H3A 0.77(2) . ? C28 C27 1.523(3) . ? C28 C19 1.544(4) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? O2 C25 1.214(3) . ? C17 C18 1.363(4) . ? C17 C16 1.414(4) . ? C17 H17 0.9300 . ? C18 C19 1.500(4) . ? C24 C25 1.506(4) . ? C24 C19 1.560(4) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.495(4) . ? C16 C15 1.344(4) . ? C16 H16 0.9300 . ? C27 C26 1.533(4) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? N4 C20 1.364(4) . ? N4 C23 1.375(5) . ? N4 H4A 0.86(4) . ? C19 C20 1.511(4) . ? C15 H15 0.9300 . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C20 C21 1.357(4) . ? C21 C22 1.413(4) . ? C21 H21 0.9300 . ? C22 C23 1.329(4) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 C11 C5 113.3(2) . . ? C14 C11 H11A 108.9 . . ? C5 C11 H11A 108.9 . . ? C14 C11 H11B 108.9 . . ? C5 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C3 C4 N1 105.5(3) . . ? C3 C4 C5 132.6(3) . . ? N1 C4 C5 121.9(3) . . ? C7 C6 N2 107.3(3) . . ? C7 C6 C5 132.1(4) . . ? N2 C6 C5 120.5(3) . . ? C1 N1 C4 111.4(3) . . ? C1 N1 H1A 130(2) . . ? C4 N1 H1A 119(2) . . ? C4 C3 C2 108.6(3) . . ? C4 C3 H3 125.7 . . ? C2 C3 H3 125.7 . . ? C13 C12 C10 111.3(3) . . ? C13 C12 H12A 109.4 . . ? C10 C12 H12A 109.4 . . ? C13 C12 H12B 109.4 . . ? C10 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C6 N2 C9 110.0(3) . . ? C6 N2 H2A 129.5(17) . . ? C9 N2 H2A 120.3(17) . . ? C8 C9 N2 106.5(3) . . ? C8 C9 H9 126.8 . . ? N2 C9 H9 126.8 . . ? C4 C5 C6 110.7(3) . . ? C4 C5 C10 110.9(3) . . ? C6 C5 C10 108.8(3) . . ? C4 C5 C11 108.2(3) . . ? C6 C5 C11 110.3(3) . . ? C10 C5 C11 108.0(3) . . ? C6 C7 C8 107.3(3) . . ? C6 C7 H7 126.4 . . ? C8 C7 H7 126.4 . . ? C12 C10 C5 111.7(2) . . ? C12 C10 H10A 109.3 . . ? C5 C10 H10A 109.3 . . ? C12 C10 H10B 109.3 . . ? C5 C10 H10B 109.3 . . ? H10A C10 H10B 107.9 . . ? C9 C8 C7 108.9(3) . . ? C9 C8 H8 125.6 . . ? C7 C8 H8 125.6 . . ? O1 C14 C13 123.1(3) . . ? O1 C14 C11 122.7(3) . . ? C13 C14 C11 114.3(3) . . ? N1 C1 C2 107.0(4) . . ? N1 C1 H1 126.5 . . ? C2 C1 H1 126.5 . . ? C1 C2 C3 107.5(4) . . ? C1 C2 H2 126.2 . . ? C3 C2 H2 126.2 . . ? C14 C13 C12 113.7(3) . . ? C14 C13 H13A 108.8 . . ? C12 C13 H13A 108.8 . . ? C14 C13 H13B 108.8 . . ? C12 C13 H13B 108.8 . . ? H13A C13 H13B 107.7 . . ? C18 N3 C15 110.7(3) . . ? C18 N3 H3A 126(2) . . ? C15 N3 H3A 123(2) . . ? C27 C28 C19 112.1(2) . . ? C27 C28 H28A 109.2 . . ? C19 C28 H28A 109.2 . . ? C27 C28 H28B 109.2 . . ? C19 C28 H28B 109.2 . . ? H28A C28 H28B 107.9 . . ? C18 C17 C16 108.3(3) . . ? C18 C17 H17 125.9 . . ? C16 C17 H17 125.9 . . ? N3 C18 C17 106.2(3) . . ? N3 C18 C19 121.9(3) . . ? C17 C18 C19 131.8(4) . . ? C25 C24 C19 114.1(3) . . ? C25 C24 H24A 108.7 . . ? C19 C24 H24A 108.7 . . ? C25 C24 H24B 108.7 . . ? C19 C24 H24B 108.7 . . ? H24A C24 H24B 107.6 . . ? O2 C25 C26 122.1(4) . . ? O2 C25 C24 122.1(3) . . ? C26 C25 C24 115.5(3) . . ? C15 C16 C17 107.2(3) . . ? C15 C16 H16 126.4 . . ? C17 C16 H16 126.4 . . ? C28 C27 C26 110.9(3) . . ? C28 C27 H27A 109.4 . . ? C26 C27 H27A 109.4 . . ? C28 C27 H27B 109.4 . . ? C26 C27 H27B 109.4 . . ? H27A C27 H27B 108.0 . . ? C20 N4 C23 109.6(4) . . ? C20 N4 H4A 131(3) . . ? C23 N4 H4A 119(3) . . ? C18 C19 C20 109.6(3) . . ? C18 C19 C28 111.8(3) . . ? C20 C19 C28 109.6(3) . . ? C18 C19 C24 109.8(3) . . ? C20 C19 C24 108.7(3) . . ? C28 C19 C24 107.2(3) . . ? C16 C15 N3 107.6(4) . . ? C16 C15 H15 126.2 . . ? N3 C15 H15 126.2 . . ? C25 C26 C27 112.7(3) . . ? C25 C26 H26A 109.0 . . ? C27 C26 H26A 109.0 . . ? C25 C26 H26B 109.0 . . ? C27 C26 H26B 109.0 . . ? H26A C26 H26B 107.8 . . ? C21 C20 N4 106.9(3) . . ? C21 C20 C19 132.5(4) . . ? N4 C20 C19 120.6(4) . . ? C20 C21 C22 107.7(4) . . ? C20 C21 H21 126.2 . . ? C22 C21 H21 126.2 . . ? C23 C22 C21 108.1(4) . . ? C23 C22 H22 126.0 . . ? C21 C22 H22 126.0 . . ? C22 C23 N4 107.7(5) . . ? C22 C23 H23 126.1 . . ? N4 C23 H23 126.1 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.141 _refine_diff_density_min -0.149 _refine_diff_density_rms 0.038 data_sanjib_s2 _database_code_depnum_ccdc_archive 'CCDC 903472' #TrackingRef 'Compound-3(polymorph-2).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 N2 O' _chemical_formula_weight 228.29 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 'Pbcn ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 16.4455(8) _cell_length_b 7.7792(3) _cell_length_c 18.8199(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2407.68(19) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1732 _cell_measurement_theta_min 2.6977 _cell_measurement_theta_max 28.8505 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9888 _exptl_absorpt_correction_T_max 0.9912 _exptl_absorpt_process_details 'SCALE3 ABSPACK' _exptl_special_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6605 _diffrn_reflns_av_R_equivalents 0.0351 _diffrn_reflns_av_sigmaI/netI 0.0610 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 28.92 _reflns_number_total 2766 _reflns_number_gt 1568 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrysAlisPro _computing_cell_refinement CrysAlisPro _computing_data_reduction CrysAlisPro _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics '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^)+(0.0460P)^2^+0.1422P] 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 2766 _refine_ls_number_parameters 162 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1170 _refine_ls_R_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.1285 _refine_ls_wR_factor_gt 0.1060 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 1.10048(11) 0.7294(2) 0.11236(10) 0.0439(5) Uani 1 1 d . . . C9 C 0.92567(12) 0.8626(2) 0.14655(10) 0.0340(5) Uani 1 1 d . . . C4 C 1.03056(12) 0.6380(2) 0.12437(10) 0.0359(5) Uani 1 1 d . . . O1 O 0.86089(10) 0.93335(17) -0.04589(8) 0.0592(5) Uani 1 1 d . . . N2 N 0.90792(13) 0.8469(2) 0.21696(10) 0.0550(6) Uani 1 1 d . . . C5 C 0.94840(12) 0.7071(2) 0.10223(10) 0.0345(5) Uani 1 1 d . . . C14 C 0.86893(13) 0.8086(2) -0.00723(11) 0.0434(5) Uani 1 1 d . . . C11 C 0.95042(12) 0.7603(2) 0.02282(10) 0.0404(5) Uani 1 1 d . . . H11A H 0.9870 0.8572 0.0175 0.049 Uiso 1 1 calc R . . H11B H 0.9724 0.6657 -0.0047 0.049 Uiso 1 1 calc R . . C10 C 0.88279(12) 0.5669(2) 0.11062(11) 0.0427(5) Uani 1 1 d . . . H10A H 0.8979 0.4673 0.0826 0.051 Uiso 1 1 calc R . . H10B H 0.8801 0.5316 0.1600 0.051 Uiso 1 1 calc R . . C7 C 0.89100(14) 1.1188(2) 0.19240(12) 0.0513(6) Uani 1 1 d . . . H7 H 0.8797 1.2356 0.1963 0.062 Uiso 1 1 calc R . . C2 C 1.13780(14) 0.4946(3) 0.16900(13) 0.0527(6) Uani 1 1 d . . . H2 H 1.1691 0.4111 0.1914 0.063 Uiso 1 1 calc R . . C12 C 0.79996(13) 0.6294(2) 0.08720(11) 0.0493(6) Uani 1 1 d . . . H12A H 0.7829 0.7230 0.1178 0.059 Uiso 1 1 calc R . . H12B H 0.7609 0.5368 0.0923 0.059 Uiso 1 1 calc R . . C8 C 0.91489(13) 1.0320(2) 0.13015(11) 0.0455(6) Uani 1 1 d . . . H8 H 0.9221 1.0815 0.0856 0.055 Uiso 1 1 calc R . . C1 C 1.16564(14) 0.6431(3) 0.13943(12) 0.0523(6) Uani 1 1 d . . . H1 H 1.2195 0.6792 0.1380 0.063 Uiso 1 1 calc R . . C3 C 1.05302(14) 0.4907(2) 0.15954(12) 0.0467(6) Uani 1 1 d . . . H3 H 1.0182 0.4037 0.1745 0.056 Uiso 1 1 calc R . . C13 C 0.80002(14) 0.6913(3) 0.01000(12) 0.0564(6) Uani 1 1 d . . . H13A H 0.8025 0.5921 -0.0211 0.068 Uiso 1 1 calc R . . H13B H 0.7493 0.7506 0.0005 0.068 Uiso 1 1 calc R . . C6 C 0.88748(15) 1.0038(2) 0.24473(12) 0.0569(6) Uani 1 1 d . . . H6 H 0.8736 1.0261 0.2917 0.068 Uiso 1 1 calc R . . H1A H 1.1022(12) 0.832(2) 0.0918(11) 0.050(6) Uiso 1 1 d . . . H2A H 0.9103(13) 0.751(3) 0.2409(14) 0.079(8) 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 N1 0.0474(11) 0.0392(9) 0.0449(11) 0.0049(8) 0.0028(10) 0.0003(9) C9 0.0368(11) 0.0322(8) 0.0330(11) 0.0026(9) 0.0025(10) 0.0008(8) C4 0.0440(12) 0.0306(8) 0.0331(11) -0.0009(8) 0.0073(11) 0.0021(9) O1 0.0683(11) 0.0537(8) 0.0557(10) 0.0199(8) -0.0062(9) 0.0012(8) N2 0.0913(16) 0.0385(9) 0.0351(10) 0.0059(8) 0.0089(11) 0.0146(10) C5 0.0424(11) 0.0278(8) 0.0332(11) 0.0036(8) 0.0054(10) -0.0004(8) C14 0.0597(14) 0.0384(10) 0.0321(11) -0.0004(9) 0.0005(12) -0.0001(10) C11 0.0509(12) 0.0361(9) 0.0344(12) 0.0027(9) 0.0051(11) 0.0008(9) C10 0.0537(13) 0.0313(9) 0.0431(12) 0.0029(9) 0.0040(12) -0.0031(9) C7 0.0678(15) 0.0304(9) 0.0556(14) -0.0050(10) 0.0060(14) 0.0051(10) C2 0.0580(15) 0.0507(12) 0.0492(14) 0.0059(11) 0.0034(13) 0.0199(11) C12 0.0481(13) 0.0400(10) 0.0598(15) 0.0054(11) 0.0003(13) -0.0125(9) C8 0.0645(15) 0.0311(9) 0.0408(12) 0.0042(9) 0.0079(12) -0.0009(10) C1 0.0447(13) 0.0642(14) 0.0482(14) -0.0027(12) 0.0033(12) 0.0092(12) C3 0.0524(13) 0.0382(10) 0.0493(13) 0.0089(10) 0.0098(13) 0.0053(10) C13 0.0600(15) 0.0529(12) 0.0565(15) 0.0052(11) -0.0125(14) -0.0114(11) C6 0.0897(18) 0.0443(11) 0.0369(12) -0.0060(10) 0.0056(14) 0.0175(12) _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 N1 C1 1.364(3) . ? N1 C4 1.371(2) . ? N1 H1A 0.885(19) . ? C9 N2 1.362(3) . ? C9 C8 1.365(2) . ? C9 C5 1.516(2) . ? C4 C3 1.374(2) . ? C4 C5 1.513(3) . ? O1 C14 1.220(2) . ? N2 C6 1.370(2) . ? N2 H2A 0.87(2) . ? C5 C10 1.543(3) . ? C5 C11 1.551(3) . ? C14 C13 1.490(3) . ? C14 C11 1.502(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C10 C12 1.512(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C7 C6 1.332(3) . ? C7 C8 1.408(3) . ? C7 H7 0.9300 . ? C2 C1 1.361(3) . ? C2 C3 1.406(3) . ? C2 H2 0.9300 . ? C12 C13 1.531(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C8 H8 0.9300 . ? C1 H1 0.9300 . ? C3 H3 0.9300 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C6 H6 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C4 110.02(17) . . ? C1 N1 H1A 125.5(13) . . ? C4 N1 H1A 124.4(13) . . ? N2 C9 C8 106.19(17) . . ? N2 C9 C5 121.07(16) . . ? C8 C9 C5 132.68(18) . . ? N1 C4 C3 106.65(18) . . ? N1 C4 C5 121.31(15) . . ? C3 C4 C5 132.00(18) . . ? C9 N2 C6 110.09(17) . . ? C9 N2 H2A 124.8(16) . . ? C6 N2 H2A 125.1(16) . . ? C4 C5 C9 110.62(16) . . ? C4 C5 C10 110.21(14) . . ? C9 C5 C10 109.60(16) . . ? C4 C5 C11 109.95(16) . . ? C9 C5 C11 108.80(14) . . ? C10 C5 C11 107.60(16) . . ? O1 C14 C13 122.3(2) . . ? O1 C14 C11 121.32(18) . . ? C13 C14 C11 116.33(17) . . ? C14 C11 C5 114.22(17) . . ? C14 C11 H11A 108.7 . . ? C5 C11 H11A 108.7 . . ? C14 C11 H11B 108.7 . . ? C5 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C12 C10 C5 111.88(14) . . ? C12 C10 H10A 109.2 . . ? C5 C10 H10A 109.2 . . ? C12 C10 H10B 109.2 . . ? C5 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? C6 C7 C8 107.77(17) . . ? C6 C7 H7 126.1 . . ? C8 C7 H7 126.1 . . ? C1 C2 C3 107.47(19) . . ? C1 C2 H2 126.3 . . ? C3 C2 H2 126.3 . . ? C10 C12 C13 112.17(19) . . ? C10 C12 H12A 109.2 . . ? C13 C12 H12A 109.2 . . ? C10 C12 H12B 109.2 . . ? C13 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C9 C8 C7 108.13(18) . . ? C9 C8 H8 125.9 . . ? C7 C8 H8 125.9 . . ? C2 C1 N1 107.8(2) . . ? C2 C1 H1 126.1 . . ? N1 C1 H1 126.1 . . ? C4 C3 C2 108.03(18) . . ? C4 C3 H3 126.0 . . ? C2 C3 H3 126.0 . . ? C14 C13 C12 113.55(18) . . ? C14 C13 H13A 108.9 . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13B 108.9 . . ? C12 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C7 C6 N2 107.81(19) . . ? C7 C6 H6 126.1 . . ? N2 C6 H6 126.1 . . ? _diffrn_measured_fraction_theta_max 0.868 _diffrn_reflns_theta_full 28.92 _diffrn_measured_fraction_theta_full 0.868 _refine_diff_density_max 0.131 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.039 data_san_s _database_code_depnum_ccdc_archive 'CCDC 903473' #TrackingRef 'Compound-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H11 N O' _chemical_formula_weight 161.20 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 'P 1 21/n 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.0240(10) _cell_length_b 5.3217(5) _cell_length_c 16.2081(16) _cell_angle_alpha 90.00 _cell_angle_beta 94.059(9) _cell_angle_gamma 90.00 _cell_volume 862.45(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1031 _cell_measurement_theta_min 3.1201 _cell_measurement_theta_max 28.9260 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9880 _exptl_absorpt_correction_T_max 0.9912 _exptl_absorpt_process_details ? _exptl_special_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3434 _diffrn_reflns_av_R_equivalents 0.0200 _diffrn_reflns_av_sigmaI/netI 0.0415 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.03 _diffrn_reflns_theta_max 28.99 _reflns_number_total 1942 _reflns_number_gt 1059 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrysAlisPro _computing_cell_refinement CrysAlisPro _computing_data_reduction CrysAlisPro _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics OLEX2 _computing_publication_material OLEX2 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0684P)^2^+0.2924P] 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 1942 _refine_ls_number_parameters 113 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1239 _refine_ls_R_factor_gt 0.0682 _refine_ls_wR_factor_ref 0.1894 _refine_ls_wR_factor_gt 0.1538 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 C5 C 0.3717(2) 0.0759(4) 0.38166(15) 0.0521(6) Uani 1 1 d . . . C9 C 0.3178(3) 0.2159(5) 0.52033(17) 0.0615(7) Uani 1 1 d . . . O1 O 0.3397(2) 0.3591(4) 0.57926(12) 0.0848(7) Uani 1 1 d . . . C10 C 0.3913(2) 0.2305(5) 0.44694(15) 0.0570(7) Uani 1 1 d . . . H10 H 0.4562 0.3547 0.4447 0.068 Uiso 1 1 calc R . . C4 C 0.4519(3) 0.0850(5) 0.31110(16) 0.0573(7) Uani 1 1 d . . . N1 N 0.5520(2) 0.2572(5) 0.30284(14) 0.0642(7) Uani 1 1 d . . . C6 C 0.2645(3) -0.1220(5) 0.38085(19) 0.0759(9) Uani 1 1 d . . . H6A H 0.2178 -0.1261 0.3264 0.091 Uiso 1 1 calc R . . H6B H 0.3063 -0.2846 0.3906 0.091 Uiso 1 1 calc R . . C3 C 0.4520(3) -0.0697(5) 0.24289(18) 0.0725(8) Uani 1 1 d . . . H3 H 0.3945 -0.2042 0.2313 0.087 Uiso 1 1 calc R . . C8 C 0.2177(3) 0.0116(7) 0.5236(2) 0.0891(10) Uani 1 1 d . . . H8A H 0.2583 -0.1276 0.5548 0.107 Uiso 1 1 calc R . . H8B H 0.1436 0.0722 0.5534 0.107 Uiso 1 1 calc R . . C1 C 0.6137(3) 0.2115(6) 0.23279(17) 0.0751(9) Uani 1 1 d . . . H1 H 0.6851 0.3020 0.2142 0.090 Uiso 1 1 calc R . . C7 C 0.1656(4) -0.0807(8) 0.4434(2) 0.1121(14) Uani 1 1 d . . . H7A H 0.0992 0.0379 0.4208 0.134 Uiso 1 1 calc R . . H7B H 0.1199 -0.2384 0.4518 0.134 Uiso 1 1 calc R . . C2 C 0.5533(3) 0.0101(6) 0.19429(19) 0.0803(9) Uani 1 1 d . . . H2 H 0.5755 -0.0612 0.1447 0.096 Uiso 1 1 calc R . . H1A H 0.579(3) 0.370(5) 0.3364(18) 0.069(9) 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 C5 0.0515(14) 0.0464(13) 0.0566(14) 0.0022(11) -0.0081(11) 0.0023(11) C9 0.0589(16) 0.0621(16) 0.0632(16) 0.0003(14) 0.0022(13) -0.0074(13) O1 0.0903(15) 0.0967(15) 0.0698(13) -0.0214(12) 0.0218(11) -0.0260(12) C10 0.0540(15) 0.0553(14) 0.0620(16) 0.0004(13) 0.0055(12) -0.0066(12) C4 0.0613(16) 0.0549(15) 0.0544(15) 0.0005(12) -0.0056(12) 0.0066(13) N1 0.0672(15) 0.0698(15) 0.0554(14) -0.0072(12) 0.0028(11) -0.0042(13) C6 0.082(2) 0.0683(17) 0.076(2) -0.0027(15) -0.0031(16) -0.0159(16) C3 0.082(2) 0.0677(17) 0.0664(18) -0.0145(15) -0.0021(15) 0.0025(16) C8 0.087(2) 0.101(2) 0.081(2) -0.0033(19) 0.0147(17) -0.032(2) C1 0.0745(19) 0.095(2) 0.0568(16) -0.0017(17) 0.0093(14) 0.0061(18) C7 0.098(3) 0.142(3) 0.098(3) -0.027(2) 0.020(2) -0.064(3) C2 0.084(2) 0.095(2) 0.0633(17) -0.0147(18) 0.0082(16) 0.0162(19) _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 C5 C10 1.344(3) . ? C5 C4 1.444(3) . ? C5 C6 1.505(4) . ? C9 O1 1.229(3) . ? C9 C10 1.445(4) . ? C9 C8 1.483(4) . ? C10 H10 0.9300 . ? C4 N1 1.372(3) . ? C4 C3 1.378(4) . ? N1 C1 1.353(3) . ? N1 H1A 0.84(3) . ? C6 C7 1.484(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C3 C2 1.395(4) . ? C3 H3 0.9300 . ? C8 C7 1.451(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C1 C2 1.361(4) . ? C1 H1 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C2 H2 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 C5 C4 123.0(2) . . ? C10 C5 C6 120.0(2) . . ? C4 C5 C6 117.0(2) . . ? O1 C9 C10 122.2(2) . . ? O1 C9 C8 120.7(3) . . ? C10 C9 C8 117.0(2) . . ? C5 C10 C9 124.1(2) . . ? C5 C10 H10 117.9 . . ? C9 C10 H10 117.9 . . ? N1 C4 C3 106.2(3) . . ? N1 C4 C5 123.4(2) . . ? C3 C4 C5 130.3(3) . . ? C1 N1 C4 110.1(3) . . ? C1 N1 H1A 122(2) . . ? C4 N1 H1A 128.1(19) . . ? C7 C6 C5 113.7(3) . . ? C7 C6 H6A 108.8 . . ? C5 C6 H6A 108.8 . . ? C7 C6 H6B 108.8 . . ? C5 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? C4 C3 C2 108.2(3) . . ? C4 C3 H3 125.9 . . ? C2 C3 H3 125.9 . . ? C7 C8 C9 114.7(3) . . ? C7 C8 H8A 108.6 . . ? C9 C8 H8A 108.6 . . ? C7 C8 H8B 108.6 . . ? C9 C8 H8B 108.6 . . ? H8A C8 H8B 107.6 . . ? N1 C1 C2 108.1(3) . . ? N1 C1 H1 125.9 . . ? C2 C1 H1 125.9 . . ? C8 C7 C6 116.5(3) . . ? C8 C7 H7A 108.2 . . ? C6 C7 H7A 108.2 . . ? C8 C7 H7B 108.2 . . ? C6 C7 H7B 108.2 . . ? H7A C7 H7B 107.3 . . ? C1 C2 C3 107.4(3) . . ? C1 C2 H2 126.3 . . ? C3 C2 H2 126.3 . . ? _diffrn_measured_fraction_theta_max 0.847 _diffrn_reflns_theta_full 28.99 _diffrn_measured_fraction_theta_full 0.847 _refine_diff_density_max 0.264 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.035 data_ss _database_code_depnum_ccdc_archive 'CCDC 914173' #TrackingRef 'Compound-5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H21 N3' _chemical_formula_weight 279.38 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 17.324(3) _cell_length_b 9.7036(13) _cell_length_c 18.044(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.045(19) _cell_angle_gamma 90.00 _cell_volume 3032.8(8) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 627 _cell_measurement_theta_min 3.0771 _cell_measurement_theta_max 28.9108 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9869 _exptl_absorpt_correction_T_max 0.9890 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '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 9081 _diffrn_reflns_av_R_equivalents 0.1008 _diffrn_reflns_av_sigmaI/netI 0.3035 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 28.97 _reflns_number_total 5382 _reflns_number_gt 883 _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^)+(0.0420P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5382 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3784 _refine_ls_R_factor_gt 0.0848 _refine_ls_wR_factor_ref 0.1851 _refine_ls_wR_factor_gt 0.1207 _refine_ls_goodness_of_fit_ref 0.771 _refine_ls_restrained_S_all 0.771 _refine_ls_shift/su_max 0.182 _refine_ls_shift/su_mean 0.029 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N2 N 0.8605(6) 0.3856(9) 1.0425(6) 0.058(3) Uani 1 1 d . . . H2AA H 0.8585 0.3100 1.0176 0.070 Uiso 1 1 calc R . . N1 N 0.6964(6) 0.5124(11) 0.9939(7) 0.067(4) Uani 1 1 d . . . H1AA H 0.7266 0.5170 1.0321 0.081 Uiso 1 1 calc R . . C5 C 0.7918(9) 0.6258(13) 0.9085(7) 0.070(4) Uani 1 1 d . . . H5 H 0.7915 0.7092 0.9391 0.084 Uiso 1 1 calc R . . C10 C 0.8645(7) 0.5466(11) 0.9306(7) 0.049(4) Uani 1 1 d . . . C11 C 0.8648(7) 0.5146(13) 1.0138(7) 0.046(3) Uani 1 1 d . . . C12 C 0.8662(8) 0.6083(13) 1.0699(8) 0.063(4) Uani 1 1 d . . . H12 H 0.8702 0.7036 1.0659 0.076 Uiso 1 1 calc R . . C15 C 0.8725(7) 0.4129(12) 0.8879(8) 0.058(4) Uani 1 1 d . . . C6 C 0.7899(7) 0.6735(12) 0.8293(7) 0.071(4) Uani 1 1 d . . . H6A H 0.7419 0.7220 0.8191 0.086 Uiso 1 1 calc R . . H6B H 0.7921 0.5944 0.7966 0.086 Uiso 1 1 calc R . . C4 C 0.7152(8) 0.5512(12) 0.9228(7) 0.063(4) Uani 1 1 d . . . N3 N 0.9438(7) 0.3581(13) 0.8718(6) 0.079(4) Uani 1 1 d . . . H33A H 0.9877 0.3953 0.8826 0.094 Uiso 1 1 calc R . . C9 C 0.9334(7) 0.6464(13) 0.9133(7) 0.056(4) Uani 1 1 d . . . H9A H 0.9307 0.7261 0.9456 0.067 Uiso 1 1 calc R . . H9B H 0.9817 0.5994 0.9240 0.067 Uiso 1 1 calc R . . C7 C 0.8601(9) 0.7719(11) 0.8144(7) 0.086(5) Uani 1 1 d . . . H7A H 0.8604 0.7986 0.7626 0.104 Uiso 1 1 calc R . . H7B H 0.8563 0.8545 0.8444 0.104 Uiso 1 1 calc R . . C16 C 0.8173(9) 0.3239(13) 0.8607(9) 0.079(5) Uani 1 1 d . . . H16 H 0.7640 0.3327 0.8638 0.095 Uiso 1 1 calc R . . C13 C 0.8602(8) 0.5296(14) 1.1359(8) 0.077(5) Uani 1 1 d . . . H13 H 0.8570 0.5645 1.1838 0.093 Uiso 1 1 calc R . . C2 C 0.5923(7) 0.4745(13) 0.9245(8) 0.062(4) Uani 1 1 d . . . H2 H 0.5423 0.4512 0.9098 0.075 Uiso 1 1 calc R . . C14 C 0.8602(7) 0.3969(16) 1.1171(7) 0.066(4) Uani 1 1 d . . . H14 H 0.8599 0.3234 1.1502 0.079 Uiso 1 1 calc R . . C8 C 0.9328(9) 0.6942(12) 0.8344(8) 0.073(5) Uani 1 1 d . . . H8A H 0.9373 0.6150 0.8019 0.088 Uiso 1 1 calc R . . H8B H 0.9771 0.7533 0.8266 0.088 Uiso 1 1 calc R . . C1 C 0.6235(8) 0.4667(12) 0.9937(8) 0.061(4) Uani 1 1 d . . . H1 H 0.5980 0.4342 1.0351 0.073 Uiso 1 1 calc R . . C3 C 0.6511(8) 0.5251(13) 0.8795(7) 0.066(4) Uani 1 1 d . . . H3 H 0.6471 0.5388 0.8285 0.080 Uiso 1 1 calc R . . C17 C 0.8583(11) 0.2175(17) 0.8273(9) 0.102(7) Uani 1 1 d . . . H17 H 0.8351 0.1442 0.8023 0.122 Uiso 1 1 calc R . . C18 C 0.9332(13) 0.2325(16) 0.8352(9) 0.115(7) Uani 1 1 d . . . H18 H 0.9712 0.1720 0.8196 0.138 Uiso 1 1 calc R . . N5 N 0.3614(7) -0.1109(11) 1.0409(6) 0.064(3) Uani 1 1 d . . . H5AA H 0.3620 -0.1850 1.0148 0.077 Uiso 1 1 calc R . . N6 N 0.1928(7) 0.0131(11) 0.9952(6) 0.059(3) Uani 1 1 d . . . H6AA H 0.2224 0.0177 1.0338 0.070 Uiso 1 1 calc R . . C28 C 0.2872(6) 0.1264(10) 0.9066(7) 0.038(3) Uani 1 1 d . . . H28 H 0.2885 0.2087 0.9381 0.046 Uiso 1 1 calc R . . C29 C 0.3657(7) 0.0181(11) 1.0133(7) 0.042(3) Uani 1 1 d . . . C22 C 0.3754(7) -0.0856(11) 0.8859(6) 0.054(4) Uani 1 1 d . . . C27 C 0.2913(8) 0.1821(10) 0.8277(6) 0.066(4) Uani 1 1 d . . . H27A H 0.2934 0.1054 0.7934 0.080 Uiso 1 1 calc R . . H27B H 0.2446 0.2339 0.8165 0.080 Uiso 1 1 calc R . . C23 C 0.3656(7) 0.0429(12) 0.9290(7) 0.051(4) Uani 1 1 d . . . C30 C 0.3674(7) 0.1054(12) 1.0721(7) 0.051(4) Uani 1 1 d . . . H30 H 0.3705 0.2010 1.0700 0.061 Uiso 1 1 calc R . . N4 N 0.4456(7) -0.1388(13) 0.8732(8) 0.101(5) Uani 1 1 d . . . H4AA H 0.4889 -0.1018 0.8863 0.121 Uiso 1 1 calc R . . C33 C 0.2133(7) 0.0536(10) 0.9268(7) 0.049(4) Uani 1 1 d . . . C26 C 0.3589(8) 0.2719(13) 0.8166(7) 0.079(5) Uani 1 1 d . . . H26A H 0.3544 0.3531 0.8476 0.094 Uiso 1 1 calc R . . H26B H 0.3596 0.3018 0.7654 0.094 Uiso 1 1 calc R . . C25 C 0.4353(8) 0.1975(14) 0.8358(8) 0.076(5) Uani 1 1 d . . . H25A H 0.4424 0.1205 0.8023 0.091 Uiso 1 1 calc R . . H25B H 0.4783 0.2605 0.8302 0.091 Uiso 1 1 calc R . . C32 C 0.3559(8) -0.1070(14) 1.1173(9) 0.073(5) Uani 1 1 d . . . H32 H 0.3483 -0.1820 1.1484 0.087 Uiso 1 1 calc R . . C31 C 0.3635(7) 0.0241(13) 1.1380(7) 0.060(4) Uani 1 1 d . . . H31 H 0.3659 0.0568 1.1865 0.072 Uiso 1 1 calc R . . C24 C 0.4332(8) 0.1461(14) 0.9146(8) 0.079(5) Uani 1 1 d . . . H24A H 0.4282 0.2244 0.9475 0.095 Uiso 1 1 calc R . . H24B H 0.4818 0.1010 0.9265 0.095 Uiso 1 1 calc R . . C21 C 0.3218(8) -0.1776(12) 0.8599(7) 0.062(4) Uani 1 1 d . . . H21 H 0.2684 -0.1696 0.8625 0.074 Uiso 1 1 calc R . . C36 C 0.1188(8) -0.0363(12) 0.9952(10) 0.072(5) Uani 1 1 d . . . H36 H 0.0909 -0.0652 1.0360 0.086 Uiso 1 1 calc R . . C35 C 0.0946(9) -0.0341(13) 0.9226(10) 0.082(5) Uani 1 1 d . . . H35 H 0.0475 -0.0666 0.9044 0.098 Uiso 1 1 calc R . . C34 C 0.1519(8) 0.0242(11) 0.8809(8) 0.070(5) Uani 1 1 d . . . H34 H 0.1492 0.0407 0.8301 0.084 Uiso 1 1 calc R . . C20 C 0.3641(10) -0.2897(11) 0.8274(8) 0.082(5) Uani 1 1 d . . . H20 H 0.3442 -0.3682 0.8044 0.099 Uiso 1 1 calc R . . C19 C 0.4379(9) -0.2558(18) 0.8377(9) 0.090(5) Uani 1 1 d . . . H19 H 0.4790 -0.3088 0.8215 0.108 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N2 0.065(7) 0.041(6) 0.069(9) 0.008(5) -0.006(8) -0.004(5) N1 0.049(7) 0.079(8) 0.073(9) 0.010(6) -0.009(8) -0.009(6) C5 0.104(11) 0.061(8) 0.046(9) 0.010(6) 0.003(10) 0.001(8) C10 0.050(8) 0.043(6) 0.053(9) -0.002(6) -0.012(8) 0.013(6) C11 0.022(6) 0.071(8) 0.045(9) 0.013(7) 0.001(7) 0.002(6) C12 0.071(9) 0.057(8) 0.060(10) -0.001(7) -0.017(9) 0.008(7) C15 0.039(7) 0.067(8) 0.071(10) 0.018(7) 0.037(8) 0.020(7) C6 0.043(7) 0.085(8) 0.087(11) 0.048(7) 0.027(9) 0.001(7) C4 0.065(10) 0.085(8) 0.039(8) 0.028(6) -0.004(9) 0.030(7) N3 0.052(7) 0.103(9) 0.081(10) 0.004(7) 0.023(9) 0.017(7) C9 0.040(7) 0.080(8) 0.047(9) -0.015(7) -0.006(8) -0.015(7) C7 0.165(16) 0.040(7) 0.055(9) -0.001(6) 0.027(11) 0.014(9) C16 0.071(9) 0.046(8) 0.119(13) -0.021(7) -0.034(10) -0.003(7) C13 0.070(9) 0.101(10) 0.060(10) -0.044(8) -0.012(9) 0.058(8) C2 0.038(7) 0.089(9) 0.061(10) -0.010(8) 0.013(9) 0.010(7) C14 0.051(8) 0.122(12) 0.026(8) 0.014(8) 0.021(8) 0.027(8) C8 0.104(12) 0.057(8) 0.060(10) 0.013(7) 0.031(10) -0.032(8) C1 0.056(9) 0.074(9) 0.053(9) 0.021(7) 0.020(9) -0.003(7) C3 0.058(9) 0.105(10) 0.036(8) 0.008(7) 0.010(9) 0.037(8) C17 0.132(15) 0.108(13) 0.063(12) -0.007(9) -0.043(12) 0.028(12) C18 0.21(2) 0.085(10) 0.056(11) -0.023(8) 0.040(15) 0.086(14) N5 0.064(7) 0.078(8) 0.052(8) -0.022(6) 0.016(8) 0.001(6) N6 0.056(8) 0.085(8) 0.036(7) 0.004(6) 0.012(7) 0.006(6) C28 0.024(5) 0.042(6) 0.049(8) -0.025(5) 0.002(7) 0.017(5) C29 0.048(8) 0.037(6) 0.041(8) -0.005(6) -0.005(8) -0.011(6) C22 0.066(9) 0.062(7) 0.032(7) -0.009(6) -0.029(7) 0.000(7) C27 0.116(11) 0.049(6) 0.033(7) -0.020(5) -0.017(8) 0.019(7) C23 0.033(7) 0.068(8) 0.053(9) -0.021(7) 0.020(8) -0.012(6) C30 0.049(8) 0.046(7) 0.058(10) -0.012(6) 0.008(8) 0.000(6) N4 0.064(8) 0.079(9) 0.159(14) -0.015(8) -0.015(10) 0.019(8) C33 0.046(8) 0.033(6) 0.069(9) -0.032(6) -0.001(8) -0.007(5) C26 0.120(12) 0.082(9) 0.034(8) 0.022(6) -0.001(9) -0.052(10) C25 0.058(9) 0.115(11) 0.054(10) -0.019(8) 0.006(9) -0.029(8) C32 0.062(9) 0.076(10) 0.079(12) 0.007(8) -0.002(10) -0.023(8) C31 0.059(8) 0.091(9) 0.030(8) 0.012(6) 0.014(8) -0.022(7) C24 0.086(11) 0.073(9) 0.079(12) 0.009(8) 0.036(11) 0.001(9) C21 0.055(8) 0.060(8) 0.070(10) -0.012(7) -0.007(9) 0.016(7) C36 0.040(8) 0.075(9) 0.101(13) -0.022(8) 0.021(10) -0.025(7) C35 0.062(10) 0.069(9) 0.113(15) -0.012(9) -0.015(12) -0.023(8) C34 0.078(10) 0.049(7) 0.082(11) -0.020(7) -0.031(10) -0.018(7) C20 0.134(15) 0.041(7) 0.071(11) -0.029(6) -0.028(11) 0.007(8) C19 0.081(11) 0.121(13) 0.069(12) -0.003(9) 0.038(12) 0.006(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N2 C14 1.350(14) . ? N2 C11 1.358(14) . ? N2 H2AA 0.8600 . ? N1 C1 1.338(16) . ? N1 C4 1.382(16) . ? N1 H1AA 0.8600 . ? C5 C6 1.501(16) . ? C5 C10 1.523(16) . ? C5 C4 1.537(18) . ? C5 H5 0.9800 . ? C10 C15 1.517(16) . ? C10 C11 1.533(17) . ? C10 C9 1.573(17) . ? C11 C12 1.361(17) . ? C12 C13 1.420(18) . ? C12 H12 0.9300 . ? C15 C16 1.372(16) . ? C15 N3 1.381(16) . ? C6 C7 1.574(16) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C4 C3 1.370(16) . ? N3 C18 1.398(18) . ? N3 H33A 0.8600 . ? C9 C8 1.497(16) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C7 C8 1.506(18) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C16 C17 1.40(2) . ? C16 H16 0.9300 . ? C13 C14 1.332(18) . ? C13 H13 0.9300 . ? C2 C1 1.354(16) . ? C2 C3 1.402(18) . ? C2 H2 0.9300 . ? C14 H14 0.9300 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C1 H1 0.9300 . ? C3 H3 0.9300 . ? C17 C18 1.31(2) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? N5 C29 1.350(14) . ? N5 C32 1.383(16) . ? N5 H5AA 0.8600 . ? N6 C33 1.349(16) . ? N6 C36 1.368(16) . ? N6 H6AA 0.8600 . ? C28 C33 1.513(16) . ? C28 C27 1.525(16) . ? C28 C23 1.627(14) . ? C28 H28 0.9800 . ? C29 C30 1.358(16) . ? C29 C23 1.540(17) . ? C22 N4 1.346(17) . ? C22 C21 1.365(15) . ? C22 C23 1.481(15) . ? C27 C26 1.477(16) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C23 C24 1.566(18) . ? C30 C31 1.429(16) . ? C30 H30 0.9300 . ? N4 C19 1.309(18) . ? N4 H4AA 0.8600 . ? C33 C34 1.366(15) . ? C26 C25 1.542(18) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C25 C24 1.507(17) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C32 C31 1.332(17) . ? C32 H32 0.9300 . ? C31 H31 0.9300 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C21 C20 1.442(18) . ? C21 H21 0.9300 . ? C36 C35 1.369(19) . ? C36 H36 0.9300 . ? C35 C34 1.38(2) . ? C35 H35 0.9300 . ? C34 H34 0.9300 . ? C20 C19 1.330(19) . ? C20 H20 0.9300 . ? C19 H19 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 N2 C11 107.9(11) . . ? C14 N2 H2AA 126.1 . . ? C11 N2 H2AA 126.0 . . ? C1 N1 C4 109.1(11) . . ? C1 N1 H1AA 125.5 . . ? C4 N1 H1AA 125.5 . . ? C6 C5 C10 114.1(13) . . ? C6 C5 C4 107.5(10) . . ? C10 C5 C4 115.5(9) . . ? C6 C5 H5 106.4 . . ? C10 C5 H5 106.3 . . ? C4 C5 H5 106.3 . . ? C15 C10 C5 112.4(9) . . ? C15 C10 C11 109.0(10) . . ? C5 C10 C11 110.3(12) . . ? C15 C10 C9 110.5(11) . . ? C5 C10 C9 105.3(9) . . ? C11 C10 C9 109.3(9) . . ? N2 C11 C12 109.4(12) . . ? N2 C11 C10 124.1(11) . . ? C12 C11 C10 126.4(12) . . ? C11 C12 C13 105.3(12) . . ? C11 C12 H12 127.4 . . ? C13 C12 H12 127.3 . . ? C16 C15 N3 107.7(12) . . ? C16 C15 C10 130.5(12) . . ? N3 C15 C10 121.7(11) . . ? C5 C6 C7 110.3(11) . . ? C5 C6 H6A 109.6 . . ? C7 C6 H6A 109.6 . . ? C5 C6 H6B 109.6 . . ? C7 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? C3 C4 N1 106.1(13) . . ? C3 C4 C5 133.2(12) . . ? N1 C4 C5 120.2(10) . . ? C15 N3 C18 108.9(13) . . ? C15 N3 H33A 125.6 . . ? C18 N3 H33A 125.5 . . ? C8 C9 C10 112.8(9) . . ? C8 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? C8 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C8 C7 C6 107.5(9) . . ? C8 C7 H7A 110.2 . . ? C6 C7 H7A 110.2 . . ? C8 C7 H7B 110.2 . . ? C6 C7 H7B 110.2 . . ? H7A C7 H7B 108.5 . . ? C15 C16 C17 105.2(14) . . ? C15 C16 H16 127.4 . . ? C17 C16 H16 127.4 . . ? C14 C13 C12 107.8(12) . . ? C14 C13 H13 126.1 . . ? C12 C13 H13 126.1 . . ? C1 C2 C3 105.8(11) . . ? C1 C2 H2 127.1 . . ? C3 C2 H2 127.1 . . ? C13 C14 N2 109.4(12) . . ? C13 C14 H14 125.3 . . ? N2 C14 H14 125.3 . . ? C9 C8 C7 111.9(13) . . ? C9 C8 H8A 109.3 . . ? C7 C8 H8A 109.2 . . ? C9 C8 H8B 109.2 . . ? C7 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? N1 C1 C2 110.1(13) . . ? N1 C1 H1 125.0 . . ? C2 C1 H1 125.0 . . ? C4 C3 C2 108.9(11) . . ? C4 C3 H3 125.5 . . ? C2 C3 H3 125.6 . . ? C18 C17 C16 112.5(15) . . ? C18 C17 H17 123.8 . . ? C16 C17 H17 123.7 . . ? C17 C18 N3 105.7(14) . . ? C17 C18 H18 127.2 . . ? N3 C18 H18 127.2 . . ? C29 N5 C32 110.4(11) . . ? C29 N5 H5AA 124.9 . . ? C32 N5 H5AA 124.8 . . ? C33 N6 C36 111.4(11) . . ? C33 N6 H6AA 124.3 . . ? C36 N6 H6AA 124.3 . . ? C33 C28 C27 116.4(9) . . ? C33 C28 C23 114.5(9) . . ? C27 C28 C23 110.9(10) . . ? C33 C28 H28 104.5 . . ? C27 C28 H28 104.5 . . ? C23 C28 H28 104.5 . . ? N5 C29 C30 106.9(12) . . ? N5 C29 C23 120.7(10) . . ? C30 C29 C23 132.4(11) . . ? N4 C22 C21 107.5(11) . . ? N4 C22 C23 121.6(11) . . ? C21 C22 C23 130.4(13) . . ? C26 C27 C28 112.7(9) . . ? C26 C27 H27A 109.0 . . ? C28 C27 H27A 109.0 . . ? C26 C27 H27B 109.1 . . ? C28 C27 H27B 109.1 . . ? H27A C27 H27B 107.8 . . ? C22 C23 C29 112.9(10) . . ? C22 C23 C24 111.0(12) . . ? C29 C23 C24 106.1(10) . . ? C22 C23 C28 113.0(9) . . ? C29 C23 C28 108.0(11) . . ? C24 C23 C28 105.3(9) . . ? C29 C30 C31 107.8(11) . . ? C29 C30 H30 126.1 . . ? C31 C30 H30 126.1 . . ? C19 N4 C22 109.4(13) . . ? C19 N4 H4AA 125.3 . . ? C22 N4 H4AA 125.3 . . ? N6 C33 C34 106.2(12) . . ? N6 C33 C28 126.5(10) . . ? C34 C33 C28 127.2(13) . . ? C27 C26 C25 112.0(10) . . ? C27 C26 H26A 109.2 . . ? C25 C26 H26A 109.2 . . ? C27 C26 H26B 109.2 . . ? C25 C26 H26B 109.2 . . ? H26A C26 H26B 107.9 . . ? C24 C25 C26 109.3(13) . . ? C24 C25 H25A 109.7 . . ? C26 C25 H25A 109.8 . . ? C24 C25 H25B 109.9 . . ? C26 C25 H25B 109.9 . . ? H25A C25 H25B 108.3 . . ? C31 C32 N5 107.3(12) . . ? C31 C32 H32 126.3 . . ? N5 C32 H32 126.3 . . ? C32 C31 C30 107.4(12) . . ? C32 C31 H31 126.3 . . ? C30 C31 H31 126.3 . . ? C25 C24 C23 113.5(12) . . ? C25 C24 H24A 108.8 . . ? C23 C24 H24A 108.8 . . ? C25 C24 H24B 108.9 . . ? C23 C24 H24B 108.9 . . ? H24A C24 H24B 107.7 . . ? C22 C21 C20 106.6(12) . . ? C22 C21 H21 126.7 . . ? C20 C21 H21 126.7 . . ? N6 C36 C35 105.3(14) . . ? N6 C36 H36 127.3 . . ? C35 C36 H36 127.4 . . ? C36 C35 C34 108.6(13) . . ? C36 C35 H35 125.7 . . ? C34 C35 H35 125.7 . . ? C33 C34 C35 108.4(14) . . ? C33 C34 H34 125.8 . . ? C35 C34 H34 125.8 . . ? C19 C20 C21 104.5(11) . . ? C19 C20 H20 127.7 . . ? C21 C20 H20 127.7 . . ? N4 C19 C20 111.9(14) . . ? N4 C19 H19 124.1 . . ? C20 C19 H19 124.1 . . ? _diffrn_measured_fraction_theta_max 0.669 _diffrn_reflns_theta_full 28.97 _diffrn_measured_fraction_theta_full 0.669 _refine_diff_density_max 0.138 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.035 data_ssa _database_code_depnum_ccdc_archive 'CCDC 914174' #TrackingRef 'Compound-6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 N2 O' _chemical_formula_weight 228.29 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 P21/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 15.4220(12) _cell_length_b 9.7194(6) _cell_length_c 17.4527(16) _cell_angle_alpha 90.00 _cell_angle_beta 110.396(10) _cell_angle_gamma 90.00 _cell_volume 2452.0(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1860 _cell_measurement_theta_min 2.8126 _cell_measurement_theta_max 28.9078 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9828 _exptl_absorpt_correction_T_max 0.9859 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '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 10629 _diffrn_reflns_av_R_equivalents 0.0635 _diffrn_reflns_av_sigmaI/netI 0.1471 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 28.97 _reflns_number_total 5547 _reflns_number_gt 1846 _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^)+(0.0992P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5547 _refine_ls_number_parameters 323 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2132 _refine_ls_R_factor_gt 0.0748 _refine_ls_wR_factor_ref 0.2186 _refine_ls_wR_factor_gt 0.1758 _refine_ls_goodness_of_fit_ref 0.851 _refine_ls_restrained_S_all 0.851 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C23 C 0.1899(2) 0.5787(3) 0.0416(2) 0.0442(9) Uani 1 1 d . . . N2 N 0.3490(2) 0.2043(3) 0.4312(2) 0.0560(9) Uani 1 1 d . . . C8 C 0.3550(2) 0.1914(4) 0.3554(2) 0.0433(9) Uani 1 1 d . . . O2 O 0.34204(17) 0.5152(3) 0.04805(18) 0.0764(9) Uani 1 1 d . . . C9 C 0.3138(2) 0.0720(3) 0.2994(2) 0.0420(9) Uani 1 1 d . . . C18 C 0.1850(2) 0.5864(3) 0.1262(2) 0.0468(9) Uani 1 1 d . . . N1 N 0.1731(2) 0.2232(4) 0.2436(2) 0.0599(9) Uani 1 1 d . . . C22 C 0.1599(2) 0.4377(4) 0.0049(2) 0.0446(9) Uani 1 1 d . . . C4 C 0.2121(2) 0.0961(4) 0.2546(2) 0.0476(9) Uani 1 1 d . . . C28 C 0.2916(3) 0.6070(4) 0.0522(2) 0.0546(10) Uani 1 1 d . . . N3 N 0.1044(3) 0.6121(4) 0.1396(3) 0.0665(10) Uani 1 1 d . . . N4 N 0.1669(3) 0.3262(4) 0.0526(3) 0.0744(11) Uani 1 1 d . . . C5 C 0.3870(3) 0.3261(4) 0.4659(3) 0.0652(12) Uani 1 1 d . . . H5 H 0.3906 0.3579 0.5172 0.078 Uiso 1 1 calc R . . C10 C 0.3266(3) -0.0656(4) 0.3472(2) 0.0652(12) Uani 1 1 d . . . H10A H 0.3032 -0.0552 0.3918 0.078 Uiso 1 1 calc R . . H10B H 0.2905 -0.1367 0.3110 0.078 Uiso 1 1 calc R . . C21 C 0.1263(2) 0.3933(4) -0.0732(2) 0.0548(10) Uani 1 1 d . . . H21 H 0.1144 0.4478 -0.1196 0.066 Uiso 1 1 calc R . . C14 C 0.3653(3) 0.0634(4) 0.2390(3) 0.0584(11) Uani 1 1 d . . . C17 C 0.2507(3) 0.5653(4) 0.2007(2) 0.0584(10) Uani 1 1 d . . . H17 H 0.3127 0.5468 0.2102 0.070 Uiso 1 1 calc R . . C20 C 0.1125(3) 0.2506(4) -0.0725(3) 0.0672(12) Uani 1 1 d . . . H20 H 0.0893 0.1937 -0.1180 0.081 Uiso 1 1 calc R . . O1 O 0.3335(2) 0.1129(4) 0.1711(2) 0.1132(12) Uani 1 1 d . . . C15 C 0.1215(4) 0.6052(5) 0.2223(4) 0.0841(15) Uani 1 1 d . . . H15 H 0.0778 0.6188 0.2472 0.101 Uiso 1 1 calc R . . C1 C 0.0809(3) 0.2147(6) 0.1998(3) 0.0774(14) Uani 1 1 d . . . H1 H 0.0396 0.2879 0.1850 0.093 Uiso 1 1 calc R . . C13 C 0.4609(3) 0.0068(5) 0.2684(3) 0.0712(12) Uani 1 1 d . . . H13A H 0.5025 0.0742 0.3034 0.085 Uiso 1 1 calc R . . H13B H 0.4802 -0.0088 0.2218 0.085 Uiso 1 1 calc R . . C3 C 0.1421(3) 0.0051(5) 0.2162(2) 0.0652(11) Uani 1 1 d . . . H3 H 0.1476 -0.0899 0.2135 0.078 Uiso 1 1 calc R . . C24 C 0.1287(3) 0.6895(4) -0.0165(2) 0.0667(12) Uani 1 1 d . . . H24A H 0.1284 0.6738 -0.0715 0.080 Uiso 1 1 calc R . . H24B H 0.0656 0.6805 -0.0176 0.080 Uiso 1 1 calc R . . C7 C 0.3983(2) 0.3085(4) 0.3435(3) 0.0612(11) Uani 1 1 d . . . H7 H 0.4122 0.3289 0.2970 0.073 Uiso 1 1 calc R . . C11 C 0.4283(3) -0.1111(4) 0.3819(3) 0.0710(12) Uani 1 1 d . . . H11A H 0.4638 -0.0437 0.4215 0.085 Uiso 1 1 calc R . . H11B H 0.4326 -0.1984 0.4099 0.085 Uiso 1 1 calc R . . C2 C 0.0605(3) 0.0827(6) 0.1818(3) 0.0817(15) Uani 1 1 d . . . H2 H 0.0024 0.0478 0.1517 0.098 Uiso 1 1 calc R . . C6 C 0.4182(3) 0.3921(4) 0.4129(3) 0.0676(12) Uani 1 1 d . . . H6 H 0.4474 0.4773 0.4208 0.081 Uiso 1 1 calc R . . C16 C 0.2105(4) 0.5758(4) 0.2609(3) 0.0785(13) Uani 1 1 d . . . H16 H 0.2400 0.5646 0.3169 0.094 Uiso 1 1 calc R . . C19 C 0.1389(3) 0.2118(4) 0.0061(3) 0.0804(14) Uani 1 1 d . . . H19 H 0.1382 0.1226 0.0252 0.096 Uiso 1 1 calc R . . C27 C 0.3252(3) 0.7526(5) 0.0686(3) 0.0818(14) Uani 1 1 d . . . H27A H 0.3855 0.7598 0.0633 0.098 Uiso 1 1 calc R . . H27B H 0.3320 0.7766 0.1244 0.098 Uiso 1 1 calc R . . C12 C 0.4692(3) -0.1259(5) 0.3150(3) 0.0788(13) Uani 1 1 d . . . H12A H 0.5339 -0.1515 0.3390 0.095 Uiso 1 1 calc R . . H12B H 0.4371 -0.1985 0.2778 0.095 Uiso 1 1 calc R . . C26 C 0.2601(4) 0.8533(5) 0.0111(3) 0.1031(18) Uani 1 1 d . . . H26A H 0.2615 0.8401 -0.0436 0.124 Uiso 1 1 calc R . . H26B H 0.2804 0.9464 0.0281 0.124 Uiso 1 1 calc R . . C25 C 0.1626(4) 0.8341(4) 0.0098(3) 0.0979(17) Uani 1 1 d . . . H25A H 0.1221 0.8998 -0.0277 0.117 Uiso 1 1 calc R . . H25B H 0.1606 0.8516 0.0639 0.117 Uiso 1 1 calc R . . H1A H 0.205(2) 0.302(4) 0.267(2) 0.051(11) Uiso 1 1 d . . . H4A H 0.195(3) 0.325(4) 0.104(3) 0.074(15) Uiso 1 1 d . . . H2A H 0.320(2) 0.147(4) 0.453(2) 0.056(12) Uiso 1 1 d . . . H3A H 0.054(3) 0.620(5) 0.104(3) 0.095(19) 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 C23 0.046(2) 0.040(2) 0.043(2) -0.0008(18) 0.0105(16) 0.0051(16) N2 0.065(2) 0.052(2) 0.052(2) -0.0105(18) 0.0216(18) -0.0114(17) C8 0.0406(19) 0.044(2) 0.045(2) 0.0007(19) 0.0137(17) 0.0000(17) O2 0.0519(16) 0.091(2) 0.086(2) -0.0227(18) 0.0241(15) 0.0015(16) C9 0.044(2) 0.042(2) 0.039(2) -0.0059(18) 0.0139(17) -0.0032(16) C18 0.050(2) 0.042(2) 0.050(3) -0.0096(19) 0.0209(19) -0.0025(17) N1 0.048(2) 0.066(3) 0.059(2) -0.002(2) 0.0106(17) -0.004(2) C22 0.046(2) 0.041(2) 0.044(2) -0.001(2) 0.0117(17) 0.0007(17) C4 0.048(2) 0.050(2) 0.042(2) -0.001(2) 0.0126(18) -0.003(2) C28 0.059(2) 0.062(3) 0.041(2) -0.002(2) 0.0146(19) -0.004(2) N3 0.062(3) 0.073(2) 0.072(3) -0.012(2) 0.032(2) 0.000(2) N4 0.117(3) 0.041(2) 0.056(3) -0.002(2) 0.019(2) -0.002(2) C5 0.064(3) 0.057(3) 0.063(3) -0.020(3) 0.007(2) 0.000(2) C10 0.084(3) 0.048(3) 0.049(2) -0.014(2) 0.005(2) 0.013(2) C21 0.060(2) 0.057(3) 0.046(3) -0.005(2) 0.0169(19) -0.0110(19) C14 0.065(3) 0.069(3) 0.039(2) 0.000(2) 0.015(2) 0.003(2) C17 0.066(3) 0.065(3) 0.046(3) -0.001(2) 0.022(2) -0.004(2) C20 0.075(3) 0.061(3) 0.070(3) -0.023(3) 0.031(2) -0.014(2) O1 0.099(2) 0.153(4) 0.091(3) 0.013(2) 0.039(2) 0.005(2) C15 0.115(4) 0.074(3) 0.093(4) -0.017(3) 0.075(4) -0.005(3) C1 0.045(3) 0.115(4) 0.066(3) 0.009(3) 0.012(2) 0.011(3) C13 0.063(3) 0.087(3) 0.070(3) -0.006(3) 0.031(2) 0.011(2) C3 0.060(3) 0.070(3) 0.062(3) -0.017(2) 0.017(2) -0.020(2) C24 0.080(3) 0.050(3) 0.054(3) 0.001(2) 0.003(2) 0.011(2) C7 0.061(2) 0.057(3) 0.063(3) 0.003(2) 0.019(2) -0.015(2) C11 0.083(3) 0.057(3) 0.063(3) 0.006(2) 0.014(2) 0.014(2) C2 0.047(3) 0.126(5) 0.064(3) -0.017(3) 0.009(2) -0.025(3) C6 0.067(3) 0.050(3) 0.076(3) -0.010(3) 0.013(2) -0.016(2) C16 0.110(4) 0.068(3) 0.057(3) -0.010(2) 0.027(3) -0.009(3) C19 0.121(4) 0.042(3) 0.081(4) -0.014(3) 0.039(3) -0.010(2) C27 0.086(3) 0.072(3) 0.090(4) -0.016(3) 0.034(3) -0.033(3) C12 0.079(3) 0.074(3) 0.080(3) -0.011(3) 0.023(3) 0.024(2) C26 0.163(5) 0.063(3) 0.083(4) 0.001(3) 0.042(4) -0.035(4) C25 0.144(5) 0.040(3) 0.080(4) 0.006(3) 0.002(3) 0.017(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 C23 C18 1.507(5) . ? C23 C22 1.516(5) . ? C23 C28 1.539(5) . ? C23 C24 1.553(5) . ? N2 C8 1.362(5) . ? N2 C5 1.366(5) . ? N2 H2A 0.88(3) . ? C8 C7 1.372(5) . ? C8 C9 1.507(5) . ? O2 C28 1.202(4) . ? C9 C4 1.508(4) . ? C9 C14 1.527(5) . ? C9 C10 1.552(5) . ? C18 C17 1.356(5) . ? C18 N3 1.366(5) . ? N1 C4 1.359(4) . ? N1 C1 1.362(5) . ? N1 H1A 0.92(3) . ? C22 N4 1.348(5) . ? C22 C21 1.349(5) . ? C4 C3 1.375(5) . ? C28 C27 1.501(5) . ? N3 C15 1.375(6) . ? N3 H3A 0.81(4) . ? N4 C19 1.355(5) . ? N4 H4A 0.85(4) . ? C5 C6 1.345(5) . ? C5 H5 0.9300 . ? C10 C11 1.537(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C21 C20 1.403(5) . ? C21 H21 0.9300 . ? C14 O1 1.213(4) . ? C14 C13 1.488(5) . ? C17 C16 1.398(5) . ? C17 H17 0.9300 . ? C20 C19 1.343(6) . ? C20 H20 0.9300 . ? C15 C16 1.332(6) . ? C15 H15 0.9300 . ? C1 C2 1.332(6) . ? C1 H1 0.9300 . ? C13 C12 1.506(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C3 C2 1.410(6) . ? C3 H3 0.9300 . ? C24 C25 1.514(5) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C7 C6 1.401(5) . ? C7 H7 0.9300 . ? C11 C12 1.514(6) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C2 H2 0.9300 . ? C6 H6 0.9300 . ? C16 H16 0.9300 . ? C19 H19 0.9300 . ? C27 C26 1.507(6) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C26 C25 1.508(6) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? 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 C18 C23 C22 110.3(3) . . ? C18 C23 C28 105.7(3) . . ? C22 C23 C28 111.1(3) . . ? C18 C23 C24 112.3(3) . . ? C22 C23 C24 108.9(3) . . ? C28 C23 C24 108.5(3) . . ? C8 N2 C5 110.3(4) . . ? C8 N2 H2A 126(2) . . ? C5 N2 H2A 124(2) . . ? N2 C8 C7 105.8(3) . . ? N2 C8 C9 123.0(3) . . ? C7 C8 C9 131.1(4) . . ? C8 C9 C4 110.1(3) . . ? C8 C9 C14 106.7(3) . . ? C4 C9 C14 110.3(3) . . ? C8 C9 C10 111.7(3) . . ? C4 C9 C10 109.1(3) . . ? C14 C9 C10 108.9(3) . . ? C17 C18 N3 106.5(4) . . ? C17 C18 C23 131.0(3) . . ? N3 C18 C23 122.4(3) . . ? C4 N1 C1 110.4(4) . . ? C4 N1 H1A 124(2) . . ? C1 N1 H1A 126(2) . . ? N4 C22 C21 106.7(4) . . ? N4 C22 C23 121.2(4) . . ? C21 C22 C23 132.0(4) . . ? N1 C4 C3 106.4(3) . . ? N1 C4 C9 123.0(3) . . ? C3 C4 C9 130.6(4) . . ? O2 C28 C27 121.6(4) . . ? O2 C28 C23 121.0(3) . . ? C27 C28 C23 117.4(3) . . ? C18 N3 C15 108.5(4) . . ? C18 N3 H3A 126(3) . . ? C15 N3 H3A 125(3) . . ? C22 N4 C19 110.4(4) . . ? C22 N4 H4A 124(3) . . ? C19 N4 H4A 124(3) . . ? C6 C5 N2 108.0(4) . . ? C6 C5 H5 126.0 . . ? N2 C5 H5 126.0 . . ? C11 C10 C9 112.3(3) . . ? C11 C10 H10A 109.1 . . ? C9 C10 H10A 109.1 . . ? C11 C10 H10B 109.1 . . ? C9 C10 H10B 109.1 . . ? H10A C10 H10B 107.9 . . ? C22 C21 C20 108.3(4) . . ? C22 C21 H21 125.9 . . ? C20 C21 H21 125.9 . . ? O1 C14 C13 119.8(4) . . ? O1 C14 C9 121.6(4) . . ? C13 C14 C9 118.2(3) . . ? C18 C17 C16 109.3(4) . . ? C18 C17 H17 125.4 . . ? C16 C17 H17 125.4 . . ? C19 C20 C21 107.1(4) . . ? C19 C20 H20 126.5 . . ? C21 C20 H20 126.5 . . ? C16 C15 N3 109.2(4) . . ? C16 C15 H15 125.4 . . ? N3 C15 H15 125.4 . . ? C2 C1 N1 107.8(4) . . ? C2 C1 H1 126.1 . . ? N1 C1 H1 126.1 . . ? C14 C13 C12 113.0(4) . . ? C14 C13 H13A 109.0 . . ? C12 C13 H13A 109.0 . . ? C14 C13 H13B 109.0 . . ? C12 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C4 C3 C2 107.2(4) . . ? C4 C3 H3 126.4 . . ? C2 C3 H3 126.4 . . ? C25 C24 C23 112.2(3) . . ? C25 C24 H24A 109.2 . . ? C23 C24 H24A 109.2 . . ? C25 C24 H24B 109.2 . . ? C23 C24 H24B 109.2 . . ? H24A C24 H24B 107.9 . . ? C8 C7 C6 108.7(4) . . ? C8 C7 H7 125.6 . . ? C6 C7 H7 125.6 . . ? C12 C11 C10 111.5(3) . . ? C12 C11 H11A 109.3 . . ? C10 C11 H11A 109.3 . . ? C12 C11 H11B 109.3 . . ? C10 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? C1 C2 C3 108.2(4) . . ? C1 C2 H2 125.9 . . ? C3 C2 H2 125.9 . . ? C5 C6 C7 107.1(4) . . ? C5 C6 H6 126.4 . . ? C7 C6 H6 126.4 . . ? C15 C16 C17 106.5(4) . . ? C15 C16 H16 126.8 . . ? C17 C16 H16 126.8 . . ? C20 C19 N4 107.6(4) . . ? C20 C19 H19 126.2 . . ? N4 C19 H19 126.2 . . ? C28 C27 C26 112.3(4) . . ? C28 C27 H27A 109.1 . . ? C26 C27 H27A 109.1 . . ? C28 C27 H27B 109.1 . . ? C26 C27 H27B 109.1 . . ? H27A C27 H27B 107.9 . . ? C13 C12 C11 110.8(3) . . ? C13 C12 H12A 109.5 . . ? C11 C12 H12A 109.5 . . ? C13 C12 H12B 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? C27 C26 C25 111.0(4) . . ? C27 C26 H26A 109.4 . . ? C25 C26 H26A 109.4 . . ? C27 C26 H26B 109.4 . . ? C25 C26 H26B 109.4 . . ? H26A C26 H26B 108.0 . . ? C26 C25 C24 110.9(4) . . ? C26 C25 H25A 109.5 . . ? C24 C25 H25A 109.5 . . ? C26 C25 H25B 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 108.1 . . ? _diffrn_measured_fraction_theta_max 0.854 _diffrn_reflns_theta_full 28.97 _diffrn_measured_fraction_theta_full 0.854 _refine_diff_density_max 0.992 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.046