data_exp_3499 _audit_creation_date 2014-05-10 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:54:37, GUI svn.r4466) ; _publ_contact_author_address ? _publ_contact_author_email ? _publ_contact_author_name '' _publ_contact_author_phone ? _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C20 H19 N3 O' _chemical_formula_sum 'C20 H19 N3 O' _chemical_formula_weight 317.38 _chemical_absolute_configuration ? _chemical_melting_point ? _chemical_oxdiff_formula 'C19 H1 N3 O1' 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' _space_group_crystal_system 'orthorhombic' _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.3512(9) _cell_length_b 12.5600(13) _cell_length_c 15.3638(16) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1611.5(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2496 _cell_measurement_temperature 180.01(10) _cell_measurement_theta_max 28.2800 _cell_measurement_theta_min 3.5770 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.76878 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour '' _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description '' _exptl_crystal_F_000 672 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_special_details ; ? ; _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_unetI/netI 0.0461 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 5965 _diffrn_reflns_point_group_measured_fraction_full 0.992 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.021 _diffrn_reflns_theta_min 2.929 _diffrn_ambient_temperature 180.01(10) _diffrn_detector_area_resol_mean 10.3914 _diffrn_measured_fraction_theta_full 0.9968 _diffrn_measured_fraction_theta_max 0.8356 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -4.00 84.00 1.0000 1.0600 omega____ theta____ kappa____ phi______ frames - 11.0142 19.0000 90.0000 88 #__ type_ start__ end____ width___ exp.time_ 2 omega -17.00 8.00 1.0000 1.0600 omega____ theta____ kappa____ phi______ frames - -11.8735 -99.0000 -180.0000 25 #__ type_ start__ end____ width___ exp.time_ 3 omega -87.00 -42.00 1.0000 1.0600 omega____ theta____ kappa____ phi______ frames - -11.8735 153.0000 168.2964 45 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0271263000 _diffrn_orient_matrix_UB_12 -0.0150611000 _diffrn_orient_matrix_UB_13 0.0420315000 _diffrn_orient_matrix_UB_21 -0.0360110000 _diffrn_orient_matrix_UB_22 -0.0506265000 _diffrn_orient_matrix_UB_23 -0.0052356000 _diffrn_orient_matrix_UB_31 0.0720834000 _diffrn_orient_matrix_UB_32 -0.0197685000 _diffrn_orient_matrix_UB_33 -0.0184034000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'SuperNova (Mo) X-ray Source' _reflns_Friedel_coverage 0.720 _reflns_Friedel_fraction_full 0.984 _reflns_Friedel_fraction_max 0.981 _reflns_number_gt 2743 _reflns_number_total 3141 _reflns_odcompleteness_completeness 99.68 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 25.97 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790' _refine_diff_density_max 0.189 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.043 _refine_ls_abs_structure_details ; Flack x determined using 1054 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack 0.5(10) _refine_ls_extinction_coef 0.027(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 219 _refine_ls_number_reflns 3141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0460 _refine_ls_R_factor_gt 0.0369 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0424P)^2^+0.0330P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0809 _refine_ls_wR_factor_ref 0.0852 _refine_special_details ; ? ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B) 2.b Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18) 2.c Idealised Me refined as rotating group: C20(H20A,H20B,H20C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary ? 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2751(3) 0.83612(17) 0.64728(12) 0.0231(5) Uani 1 1 d . . . . . C2 C 0.3311(3) 0.73484(17) 0.66670(13) 0.0249(5) Uani 1 1 d . . . . . H2 H 0.4085 0.7249 0.7113 0.030 Uiso 1 1 calc R U . . . C3 C 0.2730(3) 0.64837(19) 0.62055(13) 0.0308(5) Uani 1 1 d . . . . . H3 H 0.3091 0.5786 0.6341 0.037 Uiso 1 1 calc R U . . . C4 C 0.1626(3) 0.6636(2) 0.55476(15) 0.0372(6) Uani 1 1 d . . . . . H4 H 0.1198 0.6040 0.5247 0.045 Uiso 1 1 calc R U . . . C5 C 0.1146(3) 0.7648(2) 0.53270(14) 0.0340(6) Uani 1 1 d . . . . . H5 H 0.0425 0.7746 0.4855 0.041 Uiso 1 1 calc R U . . . C6 C 0.1694(3) 0.85255(19) 0.57811(12) 0.0268(5) Uani 1 1 d . . . . . C7 C 0.1332(3) 0.96525(19) 0.55239(15) 0.0335(6) Uani 1 1 d . . . . . H7A H 0.0543 0.9969 0.5930 0.040 Uiso 1 1 calc R U . . . H7B H 0.0882 0.9675 0.4928 0.040 Uiso 1 1 calc R U . . . C8 C 0.2906(3) 1.0265(2) 0.55610(15) 0.0383(6) Uani 1 1 d . . . . . H8A H 0.3695 0.9925 0.5168 0.046 Uiso 1 1 calc R U . . . H8B H 0.2731 1.1004 0.5358 0.046 Uiso 1 1 calc R U . . . C9 C 0.3564(3) 1.02827(17) 0.64785(15) 0.0333(6) Uani 1 1 d . . . . . H9A H 0.4733 1.0411 0.6455 0.040 Uiso 1 1 calc R U . . . H9B H 0.3069 1.0880 0.6802 0.040 Uiso 1 1 calc R U . . . C10 C 0.3432(3) 0.93168(19) 0.78268(14) 0.0272(5) Uani 1 1 d . . . . . C11 C 0.0042(3) 0.82011(18) 0.78391(13) 0.0236(5) Uani 1 1 d . . . . . C12 C -0.0808(3) 0.73822(18) 0.74610(14) 0.0294(5) Uani 1 1 d . . . . . H12 H -0.0483 0.6665 0.7546 0.035 Uiso 1 1 calc R U . . . C13 C -0.2131(3) 0.7611(2) 0.69588(15) 0.0354(6) Uani 1 1 d . . . . . H13 H -0.2723 0.7049 0.6699 0.043 Uiso 1 1 calc R U . . . C14 C -0.2599(3) 0.8652(2) 0.68324(15) 0.0356(6) Uani 1 1 d . . . . . H14 H -0.3506 0.8807 0.6481 0.043 Uiso 1 1 calc R U . . . C15 C -0.1752(3) 0.9471(2) 0.72165(14) 0.0332(6) Uani 1 1 d . . . . . H15 H -0.2072 1.0188 0.7127 0.040 Uiso 1 1 calc R U . . . C16 C -0.0430(3) 0.9245(2) 0.77338(14) 0.0284(5) Uani 1 1 d . . . . . H16 H 0.0142 0.9803 0.8012 0.034 Uiso 1 1 calc R U . . . C17 C 0.2885(3) 0.84139(17) 0.83798(13) 0.0252(5) Uani 1 1 d . . . . . C18 C 0.3736(3) 0.78945(18) 0.90122(13) 0.0282(5) Uani 1 1 d . . . . . H18 H 0.4805 0.8035 0.9190 0.034 Uiso 1 1 calc R U . . . C19 C 0.2706(3) 0.71148(19) 0.93420(13) 0.0282(5) Uani 1 1 d . . . . . C20 C 0.2989(3) 0.6343(2) 1.00677(15) 0.0404(6) Uani 1 1 d . . . . . H20A H 0.2876 0.6710 1.0627 0.061 Uiso 1 1 calc R U . . . H20B H 0.4072 0.6048 1.0019 0.061 Uiso 1 1 calc R U . . . H20C H 0.2204 0.5764 1.0032 0.061 Uiso 1 1 calc R U . . . N1 N 0.1405(2) 0.79504(14) 0.83577(11) 0.0251(4) Uani 1 1 d . . . . . N2 N 0.1289(2) 0.71421(15) 0.89484(11) 0.0277(5) Uani 1 1 d . . . . . N3 N 0.3258(2) 0.92780(14) 0.69518(11) 0.0244(4) Uani 1 1 d . . . . . O1 O 0.4038(2) 1.00940(14) 0.81844(10) 0.0410(5) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0220(11) 0.0254(12) 0.0218(10) 0.0013(9) 0.0052(9) -0.0011(9) C2 0.0240(11) 0.0291(13) 0.0214(10) 0.0008(9) 0.0019(9) 0.0024(10) C3 0.0364(13) 0.0271(13) 0.0289(11) -0.0013(10) 0.0069(10) 0.0007(10) C4 0.0438(15) 0.0371(15) 0.0307(12) -0.0093(11) -0.0012(11) -0.0049(12) C5 0.0323(13) 0.0465(17) 0.0233(11) -0.0021(11) -0.0045(10) 0.0023(12) C6 0.0251(12) 0.0340(14) 0.0212(10) 0.0019(10) 0.0030(9) 0.0031(10) C7 0.0331(14) 0.0392(15) 0.0283(11) 0.0086(11) -0.0018(10) 0.0067(11) C8 0.0431(15) 0.0339(15) 0.0380(13) 0.0146(12) 0.0048(12) 0.0031(12) C9 0.0358(14) 0.0240(13) 0.0402(12) 0.0061(11) 0.0041(11) -0.0038(11) C10 0.0242(12) 0.0285(13) 0.0290(11) -0.0021(10) -0.0023(10) -0.0014(10) C11 0.0215(11) 0.0276(13) 0.0216(10) 0.0032(9) 0.0030(8) 0.0005(9) C12 0.0258(11) 0.0274(13) 0.0351(12) 0.0022(11) 0.0011(10) -0.0004(10) C13 0.0270(12) 0.0372(16) 0.0420(13) -0.0024(11) -0.0014(11) -0.0061(11) C14 0.0247(13) 0.0468(16) 0.0352(12) 0.0044(12) -0.0022(10) 0.0042(11) C15 0.0324(14) 0.0330(14) 0.0340(12) 0.0042(10) 0.0013(11) 0.0087(10) C16 0.0303(13) 0.0281(13) 0.0268(11) 0.0016(10) 0.0020(9) -0.0013(10) C17 0.0255(12) 0.0270(12) 0.0230(10) -0.0041(10) -0.0002(9) -0.0005(10) C18 0.0292(13) 0.0317(13) 0.0238(10) -0.0034(10) -0.0051(9) 0.0025(10) C19 0.0345(13) 0.0277(13) 0.0225(10) -0.0016(10) 0.0010(10) 0.0075(10) C20 0.0397(15) 0.0430(17) 0.0386(13) 0.0133(12) -0.0027(11) 0.0093(13) N1 0.0268(10) 0.0258(10) 0.0226(8) 0.0029(8) 0.0003(8) 0.0005(8) N2 0.0308(11) 0.0259(11) 0.0264(9) 0.0069(8) 0.0009(8) 0.0040(9) N3 0.0276(10) 0.0192(10) 0.0265(9) 0.0022(8) 0.0001(8) -0.0005(8) O1 0.0491(11) 0.0349(10) 0.0389(9) -0.0040(8) -0.0102(8) -0.0133(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.388(3) . ? C1 C6 1.397(3) . ? C1 N3 1.431(3) . ? C2 H2 0.9500 . ? C2 C3 1.385(3) . ? C3 H3 0.9500 . ? C3 C4 1.381(3) . ? C4 H4 0.9500 . ? C4 C5 1.376(4) . ? C5 H5 0.9500 . ? C5 C6 1.382(3) . ? C6 C7 1.500(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C7 C8 1.525(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C8 C9 1.513(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C9 N3 1.479(3) . ? C10 C17 1.489(3) . ? C10 N3 1.353(3) . ? C10 O1 1.229(3) . ? C11 C12 1.378(3) . ? C11 C16 1.378(3) . ? C11 N1 1.425(3) . ? C12 H12 0.9500 . ? C12 C13 1.378(3) . ? C13 H13 0.9500 . ? C13 C14 1.379(4) . ? C14 H14 0.9500 . ? C14 C15 1.380(3) . ? C15 H15 0.9500 . ? C15 C16 1.390(3) . ? C16 H16 0.9500 . ? C17 C18 1.369(3) . ? C17 N1 1.367(3) . ? C18 H18 0.9500 . ? C18 C19 1.399(3) . ? C19 C20 1.496(3) . ? C19 N2 1.329(3) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? N1 N2 1.365(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 120.8(2) . . ? C2 C1 N3 121.84(19) . . ? C6 C1 N3 117.35(19) . . ? C1 C2 H2 120.3 . . ? C3 C2 C1 119.4(2) . . ? C3 C2 H2 120.3 . . ? C2 C3 H3 120.0 . . ? C4 C3 C2 120.0(2) . . ? C4 C3 H3 120.0 . . ? C3 C4 H4 119.9 . . ? C5 C4 C3 120.2(2) . . ? C5 C4 H4 119.9 . . ? C4 C5 H5 119.5 . . ? C4 C5 C6 121.1(2) . . ? C6 C5 H5 119.5 . . ? C1 C6 C7 117.9(2) . . ? C5 C6 C1 118.4(2) . . ? C5 C6 C7 123.5(2) . . ? C6 C7 H7A 110.3 . . ? C6 C7 H7B 110.3 . . ? C6 C7 C8 106.97(19) . . ? H7A C7 H7B 108.6 . . ? C8 C7 H7A 110.3 . . ? C8 C7 H7B 110.3 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C9 C8 C7 110.83(19) . . ? C9 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? C8 C9 H9A 109.1 . . ? C8 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? N3 C9 C8 112.50(19) . . ? N3 C9 H9A 109.1 . . ? N3 C9 H9B 109.1 . . ? N3 C10 C17 120.4(2) . . ? O1 C10 C17 118.43(18) . . ? O1 C10 N3 121.1(2) . . ? C12 C11 N1 118.8(2) . . ? C16 C11 C12 120.9(2) . . ? C16 C11 N1 120.27(19) . . ? C11 C12 H12 120.2 . . ? C13 C12 C11 119.6(2) . . ? C13 C12 H12 120.2 . . ? C12 C13 H13 119.9 . . ? C12 C13 C14 120.3(2) . . ? C14 C13 H13 119.9 . . ? C13 C14 H14 120.0 . . ? C13 C14 C15 120.0(2) . . ? C15 C14 H14 120.0 . . ? C14 C15 H15 120.0 . . ? C14 C15 C16 120.0(2) . . ? C16 C15 H15 120.0 . . ? C11 C16 C15 119.2(2) . . ? C11 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C18 C17 C10 127.5(2) . . ? N1 C17 C10 125.99(19) . . ? N1 C17 C18 106.51(19) . . ? C17 C18 H18 127.1 . . ? C17 C18 C19 105.7(2) . . ? C19 C18 H18 127.1 . . ? C18 C19 C20 128.8(2) . . ? N2 C19 C18 111.39(19) . . ? N2 C19 C20 119.7(2) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C17 N1 C11 129.98(18) . . ? N2 N1 C11 118.65(17) . . ? N2 N1 C17 111.37(17) . . ? C19 N2 N1 104.98(18) . . ? C1 N3 C9 119.01(16) . . ? C10 N3 C1 124.88(19) . . ? C10 N3 C9 116.06(19) . . ? _shelx_estimated_absorpt_T_max 0.992 _shelx_estimated_absorpt_T_min 0.984 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelxl_version_number 2013-3