data_compound_6 _chemical_name_systematic ? _chemical_name_common SY-2-55-1 _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 N3 O2' _chemical_formula_iupac ? _chemical_formula_weight 347.41 _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.8940(19) _cell_length_b 7.2711(11) _cell_length_c 22.184(3) _cell_angle_alpha 90 _cell_angle_beta 102.610(2) _cell_angle_gamma 90 _cell_volume 1872.2(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1973 _cell_measurement_theta_min 2.84 _cell_measurement_theta_max 24.59 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS (Sheldrick 1996)' _exptl_absorpt_correction_T_min 0.97 _exptl_absorpt_correction_T_max 0.99 _exptl_special_details 'SADABS (Sheldrick 1996)' _diffrn_ambient_temperature 150 _diffrn_source 'sealed tube' _diffrn_source_type ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart1000 CCD area detector' _diffrn_measurement_method 'Phi and Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10770 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_unetI/netI 0.0596 _diffrn_reflns_theta_min 1.754 _diffrn_reflns_theta_max 27.532 _diffrn_reflns_theta_full 25.000 _diffrn_measured_fraction_theta_max 0.983 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 25 _refine_special_details ; ; _reflns_number_total 4253 _reflns_number_gt 2712 _reflns_threshold_expression 'I > 2\s(I)' _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0871 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_gt 0.1049 _refine_ls_wR_factor_ref 0.1231 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_number_reflns 4253 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0483P)^2^+0.4569P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.226 _refine_diff_density_min -0.169 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' _computing_data_collection 'Smart (Bruker AXS)' _computing_cell_refinement 'Smart (Bruker AXS)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_flags_posn _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C C1 0.38813(13) 0.4885(2) 0.31014(7) 0.0266(4) Uani d . . . 1 . . C C2 0.41864(14) 0.4702(2) 0.37349(7) 0.0285(4) Uani d . . . 1 . . H H2 0.3693 0.4845 0.4016 0.034 Uiso calc U . R 1 . . C C3 0.53642(13) 0.4262(2) 0.38869(7) 0.0259(4) Uani d . . . 1 . . C C4 0.57462(13) 0.4178(2) 0.33493(7) 0.0264(4) Uani d . . . 1 . . H H4 0.6507 0.3881 0.3315 0.032 Uiso calc U . R 1 . . C C5 0.49155(15) 0.4504(2) 0.22227(7) 0.0327(4) Uani d . . . 1 . . H H5A 0.4889 0.5752 0.2053 0.049 Uiso calc U . R 1 . . H H5B 0.4263 0.3791 0.1991 0.049 Uiso calc U . R 1 . . H H5C 0.5638 0.391 0.2188 0.049 Uiso calc U . R 1 . . C C6 0.27720(14) 0.5446(2) 0.27042(8) 0.0288(4) Uani d . . . 1 . . C C7 0.06862(15) 0.5541(3) 0.25523(9) 0.0431(5) Uani d . . . 1 . . H H7A 0.0789 0.6807 0.2423 0.065 Uiso calc U . R 1 . . H H7B 0.0165 0.5532 0.2839 0.065 Uiso calc U . R 1 . . H H7C 0.0356 0.4794 0.2189 0.065 Uiso calc U . R 1 . . C C8 0.18053(13) 0.3140(2) 0.32174(7) 0.0274(4) Uani d . . . 1 . . C C9 0.14067(16) 0.3192(3) 0.37573(8) 0.0391(4) Uani d . . . 1 . . H H9 0.1107 0.43 0.3886 0.047 Uiso calc U . R 1 . . C C10 0.14493(18) 0.1612(4) 0.41077(9) 0.0562(6) Uani d . . . 1 . . H H10 0.1172 0.1636 0.4478 0.067 Uiso calc U . R 1 . . C C11 0.18869(18) 0.0014(3) 0.39273(13) 0.0642(7) Uani d . . . 1 . . H H11 0.1932 -0.1056 0.4177 0.077 Uiso calc U . R 1 . . C C12 0.22614(17) -0.0040(3) 0.33831(13) 0.0582(6) Uani d . . . 1 . . H H12 0.2555 -0.1154 0.3255 0.07 Uiso calc U . R 1 . . C C13 0.22127(15) 0.1518(2) 0.30227(9) 0.0379(4) Uani d . . . 1 . . H H13 0.2458 0.1473 0.2643 0.045 Uiso calc U . R 1 . . C C14 0.55470(16) 0.2340(2) 0.48141(8) 0.0388(4) Uani d . . . 1 . . H H14A 0.5881 0.1166 0.4724 0.058 Uiso calc U . R 1 . . H H14B 0.4707 0.229 0.4673 0.058 Uiso calc U . R 1 . . H H14C 0.5746 0.2568 0.526 0.058 Uiso calc U . R 1 . . C C15 0.71078(14) 0.4381(2) 0.47227(8) 0.0301(4) Uani d . . . 1 . . C C16 0.75969(14) 0.5970(2) 0.44379(7) 0.0307(4) Uani d . . . 1 . . C C17 0.69982(15) 0.7599(2) 0.42753(7) 0.0317(4) Uani d . . . 1 . . H H17 0.621 0.7685 0.4294 0.038 Uiso calc U . R 1 . . C C18 0.75489(16) 0.9096(2) 0.40859(8) 0.0379(4) Uani d . . . 1 . . H H18 0.714 1.0214 0.3981 0.045 Uiso calc U . R 1 . . C C19 0.86886(17) 0.8977(3) 0.40484(9) 0.0490(5) Uani d . . . 1 . . H H19 0.9061 1.0007 0.3914 0.059 Uiso calc U . R 1 . . C C20 0.92861(18) 0.7365(3) 0.42050(11) 0.0599(6) Uani d . . . 1 . . H H20 1.0071 0.7283 0.4179 0.072 Uiso calc U . R 1 . . C C21 0.87454(16) 0.5864(3) 0.43999(10) 0.0490(5) Uani d . . . 1 . . H H21 0.9162 0.4754 0.4508 0.059 Uiso calc U . R 1 . . N N1 0.18040(11) 0.47786(19) 0.28597(6) 0.0303(3) Uani d . . . 1 . . N N2 0.48509(11) 0.45915(18) 0.28719(6) 0.0256(3) Uani d . . . 1 . . N N3 0.60062(12) 0.38319(19) 0.44912(6) 0.0296(3) Uani d . . . 1 . . O O1 0.27258(10) 0.65489(17) 0.22777(6) 0.0405(3) Uani d . . . 1 . . O O2 0.76988(11) 0.36228(18) 0.51800(6) 0.0444(4) Uani d . . . 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0210(8) 0.0256(8) 0.0339(9) -0.0046(7) 0.0072(7) -0.0010(7) C2 0.0235(8) 0.0312(9) 0.0319(9) -0.0049(7) 0.0084(7) -0.0017(7) C3 0.0218(8) 0.0254(8) 0.0299(8) -0.0036(7) 0.0043(7) -0.0014(7) C4 0.0196(8) 0.0245(8) 0.0342(9) 0.0001(6) 0.0038(7) -0.0026(7) C5 0.0341(10) 0.0347(10) 0.0295(9) 0.0029(8) 0.0074(7) -0.0015(7) C6 0.0237(8) 0.0276(9) 0.0347(9) -0.0015(7) 0.0054(7) -0.0001(7) C7 0.0233(9) 0.0444(11) 0.0589(12) 0.0037(8) 0.0032(9) 0.0141(9) C8 0.0180(8) 0.0281(9) 0.0341(9) -0.0057(7) 0.0011(7) 0.0016(7) C9 0.0352(10) 0.0455(11) 0.0364(10) -0.0136(9) 0.0073(8) -0.0046(8) C10 0.0433(12) 0.0809(17) 0.0386(11) -0.0290(12) -0.0034(9) 0.0153(11) C11 0.0326(11) 0.0578(15) 0.0892(18) -0.0172(11) -0.0148(12) 0.0425(14) C12 0.0309(11) 0.0306(11) 0.109(2) -0.0020(9) 0.0064(12) 0.0127(12) C13 0.0262(9) 0.0308(10) 0.0564(11) -0.0043(7) 0.0083(8) -0.0034(8) C14 0.0412(11) 0.0375(10) 0.0387(10) -0.0094(8) 0.0111(8) 0.0051(8) C15 0.0274(9) 0.0295(9) 0.0319(9) 0.0009(7) 0.0033(7) -0.0003(7) C16 0.0231(8) 0.0352(9) 0.0309(9) -0.0052(7) -0.0005(7) 0.0013(7) C17 0.0266(9) 0.0338(9) 0.0324(9) -0.0034(7) 0.0018(7) 0.0022(7) C18 0.0372(10) 0.0359(10) 0.0365(10) -0.0047(8) -0.0006(8) 0.0057(8) C19 0.0382(11) 0.0514(12) 0.0561(12) -0.0151(10) 0.0076(10) 0.0121(10) C20 0.0275(10) 0.0648(15) 0.0891(17) -0.0085(10) 0.0167(11) 0.0140(13) C21 0.0273(10) 0.0464(12) 0.0719(14) 0.0002(9) 0.0075(10) 0.0118(10) N1 0.0194(7) 0.0299(8) 0.0408(8) 0.0008(6) 0.0050(6) 0.0075(6) N2 0.0222(7) 0.0259(7) 0.0291(7) -0.0007(5) 0.0065(6) -0.0027(6) N3 0.0265(7) 0.0326(8) 0.0291(7) -0.0051(6) 0.0049(6) 0.0026(6) O1 0.0326(7) 0.0425(8) 0.0451(7) -0.0024(6) 0.0060(6) 0.0154(6) O2 0.0376(7) 0.0421(8) 0.0455(8) -0.0033(6) -0.0084(6) 0.0135(6) _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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 N2 . 1.375(2) ? C1 C2 . 1.379(2) ? C1 C6 . 1.475(2) ? C2 C3 . 1.404(2) ? C2 H2 . 0.95 ? C3 C4 . 1.367(2) ? C3 N3 . 1.425(2) ? C4 N2 . 1.362(2) ? C4 H4 . 0.95 ? C5 N2 . 1.460(2) ? C5 H5A . 0.98 ? C5 H5B . 0.98 ? C5 H5C . 0.98 ? C6 O1 . 1.2323(19) ? C6 N1 . 1.361(2) ? C7 N1 . 1.464(2) ? C7 H7A . 0.98 ? C7 H7B . 0.98 ? C7 H7C . 0.98 ? C8 C13 . 1.380(2) ? C8 C9 . 1.381(2) ? C8 N1 . 1.431(2) ? C9 C10 . 1.382(3) ? C9 H9 . 0.95 ? C10 C11 . 1.368(3) ? C10 H10 . 0.95 ? C11 C12 . 1.376(4) ? C11 H11 . 0.95 ? C12 C13 . 1.380(3) ? C12 H12 . 0.95 ? C13 H13 . 0.95 ? C14 N3 . 1.470(2) ? C14 H14A . 0.98 ? C14 H14B . 0.98 ? C14 H14C . 0.98 ? C15 O2 . 1.2313(19) ? C15 N3 . 1.359(2) ? C15 C16 . 1.494(2) ? C16 C17 . 1.389(2) ? C16 C21 . 1.389(3) ? C17 C18 . 1.382(2) ? C17 H17 . 0.95 ? C18 C19 . 1.379(3) ? C18 H18 . 0.95 ? C19 C20 . 1.375(3) ? C19 H19 . 0.95 ? C20 C21 . 1.383(3) ? C20 H20 . 0.95 ? C21 H21 . 0.95 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N2 C1 C2 . . 107.87(14) ? N2 C1 C6 . . 122.32(14) ? C2 C1 C6 . . 129.61(15) ? C1 C2 C3 . . 107.07(14) ? C1 C2 H2 . . 126.5 ? C3 C2 H2 . . 126.5 ? C4 C3 C2 . . 107.75(14) ? C4 C3 N3 . . 126.79(15) ? C2 C3 N3 . . 125.26(14) ? N2 C4 C3 . . 108.43(14) ? N2 C4 H4 . . 125.8 ? C3 C4 H4 . . 125.8 ? N2 C5 H5A . . 109.5 ? N2 C5 H5B . . 109.5 ? H5A C5 H5B . . 109.5 ? N2 C5 H5C . . 109.5 ? H5A C5 H5C . . 109.5 ? H5B C5 H5C . . 109.5 ? O1 C6 N1 . . 121.88(15) ? O1 C6 C1 . . 121.51(15) ? N1 C6 C1 . . 116.46(14) ? N1 C7 H7A . . 109.5 ? N1 C7 H7B . . 109.5 ? H7A C7 H7B . . 109.5 ? N1 C7 H7C . . 109.5 ? H7A C7 H7C . . 109.5 ? H7B C7 H7C . . 109.5 ? C13 C8 C9 . . 120.33(16) ? C13 C8 N1 . . 119.73(15) ? C9 C8 N1 . . 119.94(16) ? C8 C9 C10 . . 119.2(2) ? C8 C9 H9 . . 120.4 ? C10 C9 H9 . . 120.4 ? C11 C10 C9 . . 120.7(2) ? C11 C10 H10 . . 119.6 ? C9 C10 H10 . . 119.6 ? C10 C11 C12 . . 119.8(2) ? C10 C11 H11 . . 120.1 ? C12 C11 H11 . . 120.1 ? C11 C12 C13 . . 120.3(2) ? C11 C12 H12 . . 119.9 ? C13 C12 H12 . . 119.9 ? C12 C13 C8 . . 119.6(2) ? C12 C13 H13 . . 120.2 ? C8 C13 H13 . . 120.2 ? N3 C14 H14A . . 109.5 ? N3 C14 H14B . . 109.5 ? H14A C14 H14B . . 109.5 ? N3 C14 H14C . . 109.5 ? H14A C14 H14C . . 109.5 ? H14B C14 H14C . . 109.5 ? O2 C15 N3 . . 120.65(16) ? O2 C15 C16 . . 119.32(15) ? N3 C15 C16 . . 119.98(14) ? C17 C16 C21 . . 119.16(16) ? C17 C16 C15 . . 122.99(15) ? C21 C16 C15 . . 117.47(16) ? C18 C17 C16 . . 120.04(16) ? C18 C17 H17 . . 120.0 ? C16 C17 H17 . . 120.0 ? C19 C18 C17 . . 120.40(18) ? C19 C18 H18 . . 119.8 ? C17 C18 H18 . . 119.8 ? C20 C19 C18 . . 119.94(18) ? C20 C19 H19 . . 120.0 ? C18 C19 H19 . . 120.0 ? C19 C20 C21 . . 120.11(19) ? C19 C20 H20 . . 119.9 ? C21 C20 H20 . . 119.9 ? C20 C21 C16 . . 120.36(19) ? C20 C21 H21 . . 119.8 ? C16 C21 H21 . . 119.8 ? C6 N1 C8 . . 122.59(13) ? C6 N1 C7 . . 118.62(14) ? C8 N1 C7 . . 117.67(13) ? C4 N2 C1 . . 108.85(13) ? C4 N2 C5 . . 123.84(13) ? C1 N2 C5 . . 126.93(14) ? C15 N3 C3 . . 124.43(14) ? C15 N3 C14 . . 117.58(14) ? C3 N3 C14 . . 116.16(13) ?