data_crystal001 _audit_creation_date 2014-01-21 _audit_creation_method ; Olex2 1.2 (compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736) ; _shelxl_version_number 2013-2 _publ_contact_author_address ? _publ_contact_author_email ? _publ_contact_author_name '' _publ_contact_author_phone ? _publ_section_references ; Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122 Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122 ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C22 H23 N O3' _chemical_formula_sum 'C22 H23 N O3' _chemical_formula_weight 349.41 _chemical_absolute_configuration ad _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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. ; _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, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 4.95310(10) _cell_length_b 12.3326(3) _cell_length_c 29.4659(7) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1799.91(7) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9941 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 71.496 _cell_measurement_theta_min 2.999 _shelx_estimated_absorpt_T_max 0.953 _shelx_estimated_absorpt_T_min 0.906 _exptl_absorpt_coefficient_mu 0.684 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.9407 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0451 before and 0.0347 after correction. The Ratio of minimum to maximum transmission is 0.9407. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_meas . _exptl_crystal_density_method ? _exptl_crystal_description ? _exptl_crystal_F_000 744 _exptl_crystal_size_max 0.147 _exptl_crystal_size_mid 0.142 _exptl_crystal_size_min 0.071 _exptl_special_details ; ? ; _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_unetI/netI 0.0118 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_number 31273 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 71.513 _diffrn_reflns_theta_min 2.999 _diffrn_ambient_temperature 120.0 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator 'graphite' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_source ? _diffrn_standards_number 0 _reflns_Friedel_coverage 0.683 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.994 _reflns_number_gt 3442 _reflns_number_total 3492 _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 ? _computing_data_collection ? _computing_data_reduction 'SAINT v8.27A (Bruker, 2012)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 0.186 _refine_diff_density_min -0.128 _refine_diff_density_rms 0.028 _refine_ls_abs_structure_details ; Flack x determined using 1391 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack 0.04(4) _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 236 _refine_ls_number_reflns 3492 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0249 _refine_ls_R_factor_gt 0.0244 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0327P)^2^+0.2965P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0617 _refine_ls_wR_factor_ref 0.0627 _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 Ternary CH refined with riding coordinates: C7(H7), C10(H10) 2.b Secondary CH2 refined with riding coordinates: C8(H8A,H8B), C9(H9A,H9B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B) 2.c Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C5(H5), C17(H17), C18(H18), C19(H19), C20(H20) 2.d Idealised Me refined as rotating group: C11(H11A,H11B,H11C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _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 O1 O 0.1865(2) 0.29690(7) 0.05664(3) 0.0245(2) Uani 1 1 d . . . . . O2 O 0.3365(2) -0.11386(8) -0.17996(4) 0.0314(2) Uani 1 1 d . . . . . O3 O -0.3380(2) -0.34556(9) -0.13677(3) 0.0327(2) Uani 1 1 d . . . . . N1 N -0.0202(2) -0.21165(10) -0.14993(4) 0.0242(3) Uani 1 1 d . . . . . C1 C 0.0206(3) 0.27461(11) 0.09261(4) 0.0209(3) Uani 1 1 d . . . . . C2 C -0.1328(3) 0.35134(11) 0.11502(5) 0.0273(3) Uani 1 1 d . . . . . H2 H -0.1235 0.4260 0.1071 0.033 Uiso 1 1 calc R . . . . C3 C -0.3012(3) 0.31491(13) 0.14956(5) 0.0316(3) Uani 1 1 d . . . . . H3 H -0.4118 0.3654 0.1653 0.038 Uiso 1 1 calc R . . . . C4 C -0.3105(3) 0.20609(13) 0.16145(5) 0.0307(3) Uani 1 1 d . . . . . H4 H -0.4258 0.1831 0.1853 0.037 Uiso 1 1 calc R . . . . C5 C -0.1520(3) 0.13023(12) 0.13857(5) 0.0263(3) Uani 1 1 d . . . . . H5 H -0.1579 0.0558 0.1468 0.032 Uiso 1 1 calc R . . . . C6 C 0.0136(3) 0.16524(11) 0.10381(4) 0.0204(3) Uani 1 1 d . . . . . C7 C 0.1847(3) 0.10379(10) 0.06973(4) 0.0204(3) Uani 1 1 d . . . . . H7 H 0.3102 0.0525 0.0854 0.024 Uiso 1 1 calc R . . . . C8 C 0.3416(3) 0.19860(11) 0.04809(5) 0.0242(3) Uani 1 1 d . . . . . H8A H 0.5235 0.2046 0.0618 0.029 Uiso 1 1 calc R . . . . H8B H 0.3622 0.1868 0.0150 0.029 Uiso 1 1 calc R . . . . C9 C 0.0046(3) 0.04354(11) 0.03560(5) 0.0213(3) Uani 1 1 d . . . . . H9A H -0.1025 0.0978 0.0186 0.026 Uiso 1 1 calc R . . . . H9B H -0.1237 -0.0024 0.0527 0.026 Uiso 1 1 calc R . . . . C10 C 0.1550(3) -0.02832(10) 0.00130(4) 0.0201(3) Uani 1 1 d . . . . . H10 H 0.3082 0.0145 -0.0116 0.024 Uiso 1 1 calc R . . . . C11 C 0.2713(3) -0.12883(12) 0.02459(5) 0.0257(3) Uani 1 1 d . . . . . H11A H 0.1243 -0.1710 0.0381 0.039 Uiso 1 1 calc GR . . . . H11B H 0.3978 -0.1064 0.0484 0.039 Uiso 1 1 calc GR . . . . H11C H 0.3664 -0.1734 0.0022 0.039 Uiso 1 1 calc GR . . . . C12 C -0.0366(3) -0.05811(11) -0.03750(5) 0.0226(3) Uani 1 1 d . . . . . H12A H -0.1960 -0.0951 -0.0245 0.027 Uiso 1 1 calc R . . . . H12B H -0.1008 0.0097 -0.0518 0.027 Uiso 1 1 calc R . . . . C13 C 0.0828(3) -0.13061(11) -0.07440(5) 0.0208(3) Uani 1 1 d . . . . . H13A H 0.2610 -0.1020 -0.0838 0.025 Uiso 1 1 calc R . . . . H13B H 0.1092 -0.2048 -0.0623 0.025 Uiso 1 1 calc R . . . . C14 C -0.1050(3) -0.13451(12) -0.11517(5) 0.0275(3) Uani 1 1 d . . . . . H14A H -0.2885 -0.1541 -0.1047 0.033 Uiso 1 1 calc R . . . . H14B H -0.1150 -0.0613 -0.1288 0.033 Uiso 1 1 calc R . . . . C15 C 0.1940(3) -0.19356(11) -0.17971(4) 0.0236(3) Uani 1 1 d . . . . . C16 C 0.2034(3) -0.29044(11) -0.21000(4) 0.0239(3) Uani 1 1 d . . . . . C17 C 0.3734(3) -0.31433(13) -0.24585(5) 0.0304(3) Uani 1 1 d . . . . . H17 H 0.5069 -0.2644 -0.2558 0.036 Uiso 1 1 calc R . . . . C18 C 0.3401(4) -0.41502(14) -0.26674(5) 0.0350(4) Uani 1 1 d . . . . . H18 H 0.4546 -0.4346 -0.2913 0.042 Uiso 1 1 calc R . . . . C19 C 0.1438(4) -0.48675(13) -0.25237(5) 0.0353(4) Uani 1 1 d . . . . . H19 H 0.1284 -0.5552 -0.2669 0.042 Uiso 1 1 calc R . . . . C20 C -0.0325(3) -0.46117(12) -0.21697(5) 0.0308(3) Uani 1 1 d . . . . . H20 H -0.1705 -0.5098 -0.2077 0.037 Uiso 1 1 calc R . . . . C21 C 0.0032(3) -0.36166(11) -0.19608(5) 0.0243(3) Uani 1 1 d . . . . . C22 C -0.1455(3) -0.31138(12) -0.15766(4) 0.0243(3) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0272(5) 0.0199(5) 0.0264(5) 0.0013(4) 0.0028(4) -0.0012(4) O2 0.0352(6) 0.0258(5) 0.0333(5) 0.0020(4) -0.0003(5) -0.0042(5) O3 0.0311(6) 0.0394(6) 0.0278(5) 0.0024(5) 0.0005(5) -0.0057(5) N1 0.0251(6) 0.0253(6) 0.0223(5) -0.0035(5) -0.0007(5) 0.0018(5) C1 0.0204(6) 0.0225(6) 0.0199(6) -0.0007(5) -0.0038(5) -0.0012(6) C2 0.0317(8) 0.0204(6) 0.0298(7) -0.0031(5) -0.0035(6) 0.0024(6) C3 0.0326(8) 0.0314(7) 0.0308(7) -0.0093(6) 0.0028(7) 0.0070(7) C4 0.0334(8) 0.0353(8) 0.0236(7) -0.0034(6) 0.0069(6) -0.0013(7) C5 0.0321(8) 0.0242(6) 0.0226(6) 0.0007(5) 0.0016(6) -0.0011(6) C6 0.0213(7) 0.0205(6) 0.0194(6) -0.0013(5) -0.0024(5) 0.0008(5) C7 0.0200(7) 0.0193(6) 0.0219(6) -0.0009(5) -0.0001(5) 0.0013(6) C8 0.0228(7) 0.0227(6) 0.0271(6) -0.0036(5) 0.0034(6) -0.0012(6) C9 0.0198(6) 0.0198(6) 0.0243(6) -0.0018(5) 0.0020(6) 0.0007(5) C10 0.0205(6) 0.0168(6) 0.0229(6) -0.0009(5) 0.0029(6) 0.0005(5) C11 0.0309(8) 0.0201(6) 0.0261(7) -0.0008(5) -0.0008(6) 0.0045(6) C12 0.0213(6) 0.0209(6) 0.0255(7) -0.0029(5) 0.0004(6) 0.0030(6) C13 0.0222(7) 0.0172(6) 0.0231(6) -0.0014(5) 0.0014(5) -0.0001(5) C14 0.0268(8) 0.0292(7) 0.0264(7) -0.0064(6) -0.0001(6) 0.0062(6) C15 0.0241(7) 0.0241(7) 0.0226(6) 0.0016(5) -0.0022(6) 0.0037(6) C16 0.0250(7) 0.0264(7) 0.0205(6) 0.0001(5) -0.0053(5) 0.0049(6) C17 0.0283(8) 0.0393(8) 0.0235(7) 0.0001(6) -0.0009(6) 0.0056(7) C18 0.0355(8) 0.0455(9) 0.0240(7) -0.0079(6) -0.0048(7) 0.0151(8) C19 0.0435(9) 0.0321(8) 0.0304(8) -0.0124(6) -0.0147(8) 0.0115(7) C20 0.0340(8) 0.0271(7) 0.0313(7) -0.0024(6) -0.0117(7) 0.0019(7) C21 0.0259(7) 0.0259(7) 0.0211(6) 0.0004(5) -0.0063(6) 0.0039(6) C22 0.0248(7) 0.0267(7) 0.0213(6) 0.0016(5) -0.0055(6) 0.0012(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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.3693(17) . ? O1 C8 1.4571(17) . ? O2 C15 1.2099(18) . ? O3 C22 1.2110(19) . ? N1 C14 1.4596(17) . ? N1 C15 1.3951(19) . ? N1 C22 1.3961(18) . ? C1 C2 1.381(2) . ? C1 C6 1.3891(19) . ? C2 C3 1.391(2) . ? C3 C4 1.388(2) . ? C4 C5 1.395(2) . ? C5 C6 1.381(2) . ? C6 C7 1.5169(19) . ? C7 C8 1.5418(18) . ? C7 C9 1.5360(18) . ? C9 C10 1.5367(18) . ? C10 C11 1.5294(18) . ? C10 C12 1.5307(19) . ? C12 C13 1.5270(18) . ? C13 C14 1.520(2) . ? C15 C16 1.4920(18) . ? C16 C17 1.382(2) . ? C16 C21 1.387(2) . ? C17 C18 1.396(2) . ? C18 C19 1.381(3) . ? C19 C20 1.397(2) . ? C20 C21 1.384(2) . ? C21 C22 1.486(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 C1 O1 C8 106.45(10) . . ? C15 N1 C14 123.77(12) . . ? C15 N1 C22 112.10(11) . . ? C22 N1 C14 124.12(12) . . ? O1 C1 C2 124.23(13) . . ? O1 C1 C6 113.18(12) . . ? C2 C1 C6 122.56(13) . . ? C1 C2 C3 117.28(13) . . ? C4 C3 C2 121.14(14) . . ? C3 C4 C5 120.52(14) . . ? C6 C5 C4 118.88(13) . . ? C1 C6 C7 108.30(12) . . ? C5 C6 C1 119.62(13) . . ? C5 C6 C7 131.80(12) . . ? C6 C7 C8 100.17(10) . . ? C6 C7 C9 110.53(11) . . ? C9 C7 C8 112.88(11) . . ? O1 C8 C7 107.09(11) . . ? C7 C9 C10 115.34(11) . . ? C11 C10 C9 110.80(11) . . ? C11 C10 C12 111.97(11) . . ? C12 C10 C9 109.21(11) . . ? C13 C12 C10 115.61(12) . . ? C14 C13 C12 110.14(11) . . ? N1 C14 C13 113.53(12) . . ? O2 C15 N1 125.27(13) . . ? O2 C15 C16 128.96(13) . . ? N1 C15 C16 105.77(12) . . ? C17 C16 C15 130.29(14) . . ? C17 C16 C21 121.76(14) . . ? C21 C16 C15 107.94(12) . . ? C16 C17 C18 117.06(15) . . ? C19 C18 C17 121.18(15) . . ? C18 C19 C20 121.64(14) . . ? C21 C20 C19 116.91(16) . . ? C16 C21 C22 108.38(12) . . ? C20 C21 C16 121.42(14) . . ? C20 C21 C22 130.20(15) . . ? O3 C22 N1 125.00(13) . . ? O3 C22 C21 129.22(14) . . ? N1 C22 C21 105.77(12) . . ? #============================================================================== # Schley, Caltech 1/21/2014 # Collected: Oliver, Notre Dame 6/2013