# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #TrackingRef '- PRG.cif' _publ_contact_author 'Andrei S.Batsanov' _publ_contact_author_email a.s.batsanov@durham.ac.uk _journal_volume ? _journal_page_first ? _journal_page_last ? _journal_year ? _database_code_depnum_ccdc_journal ? _publ_section_title ; A Multicomponent [1+2+2+1] Cycloaddition for the Synthesis of Dihydropyridines ; _publ_contact_author_name 'Andrei S.Batsanov' loop_ _publ_author_name A.Whiting P.Girling A.Batsanov 'Hong Shen' #====================================================================== data_\a-4a _database_code_depnum_ccdc_archive 'CCDC 869480' #TrackingRef '- PRG.cif' _audit_creation_date 2011-11-30 _audit_creation_method ; Olex2 1.1-beta (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; 1,1'-(1-Benzyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-diyl)diethanone ; _chemical_formula_moiety 'C22 H20 N2 O4' _chemical_formula_sum 'C22 H20 N2 O4' _chemical_formula_weight 376.40 _chemical_melting_point 457.7(5) 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 monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_length_a 12.4631(6) _cell_length_b 11.0700(5) _cell_length_c 26.6746(12) _cell_angle_alpha 90.00 _cell_angle_beta 99.542(7) _cell_angle_gamma 90.00 _cell_volume 3629.3(3) _cell_formula_units_Z 8 _cell_measurement_reflns_used 9919 _cell_measurement_temperature 120 _cell_measurement_theta_max 29.946 _cell_measurement_theta_min 2.476 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_T_max 0.7460 _exptl_absorpt_correction_T_min 0.6326 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. R(int) was 0.1071 before and 0.0461 after correction. The Ratio of minimum to maximum transmission is 0.8480. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'light yellow' _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description blade _exptl_crystal_F_000 1584 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 0.00 1.00 0.0150 0.00 0.00 -1.00 0.0150 -1.00 0.00 0.00 0.1350 1.00 0.00 0.00 0.1350 1.00 1.00 0.00 0.3500 0.00 -2.00 1.00 0.3900 -3.00 2.00 -5.00 0.2000 _exptl_crystal_size_max 0.84 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.03 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 5 sets of \w scans each set at different \f and/or 2\q angles and each scan (15 s exposure) covering -0.300\% degrees in \w. The crystal to detector distance was 4.85 cm. ; _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_unetI/netI 0.0212 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_number 31575 _diffrn_reflns_theta_full 29.99 _diffrn_reflns_theta_max 29.99 _diffrn_reflns_theta_min 2.48 _diffrn_ambient_temperature 120 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'sealed X-ray tube' _diffrn_source_current 35.0 _diffrn_source_power 1.75 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _reflns_number_gt 4253 _reflns_number_total 5306 _reflns_threshold_expression I>2\s(I) _computing_cell_refinement 'SAINT v7.46A (Bruker, 2008)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v7.46A (Bruker, 2008)' _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 ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.424 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.053 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 257 _refine_ls_number_reflns 5306 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0413 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0619P)^2^+2.2208P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1068 _refine_ls_wR_factor_ref 0.1170 _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. Methyl groups were refined as rigid bodies rotating around C---C bonds, with a common refined U for three H atoms. Other H atoms: riding model. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.52556(7) 0.85770(8) 0.15981(4) 0.0318(2) Uani 1 1 d . . . O2 O 0.20944(7) 0.71730(7) 0.24057(3) 0.02547(18) Uani 1 1 d . . . O3 O 0.07826(8) 0.92277(9) -0.01962(3) 0.0351(2) Uani 1 1 d . . . O4 O 0.05834(7) 0.73271(9) -0.03836(3) 0.0309(2) Uani 1 1 d . . . N1 N 0.45053(8) 0.44403(8) 0.18088(4) 0.02247(19) Uani 1 1 d . . . N2 N 0.09369(8) 0.81525(10) -0.00953(4) 0.0243(2) Uani 1 1 d . . . C1 C 0.48622(10) 0.31877(10) 0.17698(4) 0.0257(2) Uani 1 1 d . . . H1A H 0.4590 0.2701 0.2034 0.031 Uiso 1 1 calc R . . H1B H 0.5667 0.3165 0.1842 0.031 Uiso 1 1 calc R . . C2 C 0.50935(9) 0.53772(11) 0.16459(4) 0.0221(2) Uani 1 1 d . . . H2 H 0.5750 0.5192 0.1525 0.026 Uiso 1 1 calc R . . C3 C 0.47801(9) 0.65415(10) 0.16504(4) 0.0204(2) Uani 1 1 d . . . C4 C 0.36839(8) 0.68875(9) 0.17893(4) 0.01830(19) Uani 1 1 d . . . H4 H 0.3787 0.7603 0.2021 0.022 Uiso 1 1 calc R . . C5 C 0.32447(9) 0.58473(9) 0.20647(4) 0.0186(2) Uani 1 1 d . . . C6 C 0.36253(9) 0.47065(10) 0.20385(4) 0.0199(2) Uani 1 1 d . . . H6 H 0.3271 0.4068 0.2184 0.024 Uiso 1 1 calc R . . C7 C 0.54872(9) 0.75230(11) 0.15228(4) 0.0245(2) Uani 1 1 d . . . C8 C 0.64983(10) 0.72309(13) 0.12995(5) 0.0337(3) Uani 1 1 d . . . H8A H 0.6811 0.7980 0.1191 0.059(3) Uiso 1 1 d R . . H8B H 0.6306 0.6695 0.1006 0.059(3) Uiso 1 1 d R . . H8C H 0.7032 0.6830 0.1557 0.059(3) Uiso 1 1 d R . . C9 C 0.23686(9) 0.61167(10) 0.23526(4) 0.0199(2) Uani 1 1 d . . . C10 C 0.17839(10) 0.51044(11) 0.25741(5) 0.0271(2) Uani 1 1 d . . . H10A H 0.1349 0.5438 0.2816 0.049(3) Uiso 1 1 d R . . H10B H 0.2318 0.4533 0.2750 0.049(3) Uiso 1 1 d R . . H10C H 0.1305 0.4686 0.2300 0.049(3) Uiso 1 1 d R . . C11 C 0.44826(9) 0.26093(10) 0.12575(4) 0.0212(2) Uani 1 1 d . . . C12 C 0.45818(10) 0.13584(10) 0.12143(5) 0.0255(2) Uani 1 1 d . . . H12 H 0.4865 0.0894 0.1506 0.031 Uiso 1 1 calc R . . C13 C 0.42705(10) 0.07886(11) 0.07498(5) 0.0307(3) Uani 1 1 d . . . H13 H 0.4340 -0.0063 0.0724 0.037 Uiso 1 1 calc R . . C14 C 0.38579(10) 0.14647(12) 0.03235(5) 0.0319(3) Uani 1 1 d . . . H14 H 0.3638 0.1076 0.0006 0.038 Uiso 1 1 calc R . . C15 C 0.37665(10) 0.27095(11) 0.03615(5) 0.0279(2) Uani 1 1 d . . . H15 H 0.3490 0.3172 0.0069 0.034 Uiso 1 1 calc R . . C16 C 0.40779(9) 0.32822(10) 0.08268(4) 0.0228(2) Uani 1 1 d . . . H16 H 0.4014 0.4135 0.0851 0.027 Uiso 1 1 calc R . . C17 C 0.28977(8) 0.72312(9) 0.13074(4) 0.01753(19) Uani 1 1 d . . . C18 C 0.23893(9) 0.63361(10) 0.09832(4) 0.0206(2) Uani 1 1 d . . . H18 H 0.2489 0.5511 0.1078 0.025 Uiso 1 1 calc R . . C19 C 0.17411(9) 0.66313(10) 0.05246(4) 0.0218(2) Uani 1 1 d . . . H19 H 0.1406 0.6018 0.0303 0.026 Uiso 1 1 calc R . . C20 C 0.15946(8) 0.78378(10) 0.03978(4) 0.0200(2) Uani 1 1 d . . . C21 C 0.20593(9) 0.87550(10) 0.07145(4) 0.0228(2) Uani 1 1 d . . . H21 H 0.1932 0.9579 0.0624 0.027 Uiso 1 1 calc R . . C22 C 0.27162(9) 0.84403(10) 0.11688(4) 0.0216(2) Uani 1 1 d . . . H22 H 0.3047 0.9058 0.1389 0.026 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 O1 0.0316(5) 0.0249(4) 0.0378(5) 0.0008(4) 0.0021(4) -0.0066(3) O2 0.0288(4) 0.0213(4) 0.0271(4) -0.0012(3) 0.0065(3) 0.0054(3) O3 0.0434(5) 0.0328(5) 0.0285(4) 0.0099(4) 0.0040(4) 0.0148(4) O4 0.0298(4) 0.0394(5) 0.0220(4) -0.0006(4) -0.0001(3) 0.0031(4) N1 0.0277(5) 0.0176(4) 0.0228(4) 0.0015(3) 0.0061(3) 0.0053(4) N2 0.0224(4) 0.0308(5) 0.0202(4) 0.0045(4) 0.0054(3) 0.0069(4) C1 0.0332(6) 0.0194(5) 0.0242(5) 0.0018(4) 0.0041(4) 0.0096(4) C2 0.0210(5) 0.0252(5) 0.0199(5) 0.0002(4) 0.0031(4) 0.0029(4) C3 0.0196(5) 0.0226(5) 0.0184(5) 0.0013(4) 0.0012(4) -0.0008(4) C4 0.0215(5) 0.0160(4) 0.0173(4) 0.0006(4) 0.0027(4) 0.0011(4) C5 0.0217(5) 0.0181(5) 0.0158(4) 0.0005(4) 0.0023(4) 0.0007(4) C6 0.0240(5) 0.0192(5) 0.0165(4) 0.0011(4) 0.0031(4) 0.0009(4) C7 0.0208(5) 0.0284(6) 0.0225(5) 0.0030(4) -0.0014(4) -0.0035(4) C8 0.0229(5) 0.0429(8) 0.0359(7) 0.0082(6) 0.0064(5) -0.0031(5) C9 0.0228(5) 0.0208(5) 0.0157(4) 0.0002(4) 0.0017(4) 0.0019(4) C10 0.0299(6) 0.0257(6) 0.0281(6) 0.0025(4) 0.0117(4) 0.0004(4) C11 0.0196(5) 0.0196(5) 0.0259(5) 0.0010(4) 0.0081(4) 0.0018(4) C12 0.0273(5) 0.0198(5) 0.0315(6) 0.0040(4) 0.0113(4) 0.0013(4) C13 0.0319(6) 0.0195(5) 0.0424(7) -0.0035(5) 0.0116(5) -0.0045(4) C14 0.0307(6) 0.0308(6) 0.0340(6) -0.0086(5) 0.0045(5) -0.0069(5) C15 0.0250(5) 0.0296(6) 0.0283(6) 0.0014(5) 0.0015(4) -0.0016(5) C16 0.0213(5) 0.0202(5) 0.0270(5) 0.0017(4) 0.0045(4) 0.0012(4) C17 0.0183(4) 0.0176(5) 0.0171(4) 0.0010(4) 0.0044(3) 0.0019(4) C18 0.0228(5) 0.0171(5) 0.0215(5) 0.0007(4) 0.0020(4) 0.0015(4) C19 0.0214(5) 0.0218(5) 0.0216(5) -0.0009(4) 0.0022(4) 0.0009(4) C20 0.0190(5) 0.0245(5) 0.0170(4) 0.0036(4) 0.0045(4) 0.0046(4) C21 0.0276(5) 0.0188(5) 0.0227(5) 0.0035(4) 0.0060(4) 0.0044(4) C22 0.0270(5) 0.0171(5) 0.0208(5) -0.0002(4) 0.0043(4) 0.0011(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.2265(15) . ? O2 C9 1.2330(13) . ? O3 N2 1.2284(13) . ? O4 N2 1.2280(14) . ? N1 C1 1.4651(14) . ? N1 C2 1.3811(15) . ? N1 C6 1.3742(14) . ? N2 C20 1.4715(14) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C1 C11 1.5123(16) . ? C2 H2 0.9500 . ? C2 C3 1.3474(15) . ? C3 C4 1.5226(15) . ? C3 C7 1.4739(16) . ? C4 H4 1.0000 . ? C4 C5 1.5161(14) . ? C4 C17 1.5297(14) . ? C5 C6 1.3548(15) . ? C5 C9 1.4659(15) . ? C6 H6 0.9500 . ? C7 C8 1.5152(18) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9801 . ? C9 C10 1.5095(16) . ? C10 H10A 0.9800 . ? C10 H10B 0.9802 . ? C10 H10C 0.9800 . ? C11 C12 1.3968(15) . ? C11 C16 1.3916(16) . ? C12 H12 0.9500 . ? C12 C13 1.3872(18) . ? C13 H13 0.9500 . ? C13 C14 1.3868(19) . ? C14 H14 0.9500 . ? C14 C15 1.3878(18) . ? C15 H15 0.9500 . ? C15 C16 1.3904(16) . ? C16 H16 0.9500 . ? C17 C18 1.3961(15) . ? C17 C22 1.3969(15) . ? C18 H18 0.9500 . ? C18 C19 1.3887(15) . ? C19 H19 0.9500 . ? C19 C20 1.3825(15) . ? C20 C21 1.3849(16) . ? C21 H21 0.9500 . ? C21 C22 1.3897(15) . ? C22 H22 0.9500 . ? 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 N1 C1 120.34(10) . . ? C6 N1 C1 120.59(10) . . ? C6 N1 C2 118.93(9) . . ? O3 N2 C20 117.97(10) . . ? O4 N2 O3 123.83(10) . . ? O4 N2 C20 118.19(10) . . ? N1 C1 H1A 108.7 . . ? N1 C1 H1B 108.7 . . ? N1 C1 C11 114.31(9) . . ? H1A C1 H1B 107.6 . . ? C11 C1 H1A 108.7 . . ? C11 C1 H1B 108.7 . . ? N1 C2 H2 118.5 . . ? C3 C2 N1 123.08(10) . . ? C3 C2 H2 118.5 . . ? C2 C3 C4 121.05(10) . . ? C2 C3 C7 121.19(10) . . ? C7 C3 C4 117.76(10) . . ? C3 C4 H4 108.7 . . ? C3 C4 C17 109.49(8) . . ? C5 C4 C3 109.72(9) . . ? C5 C4 H4 108.7 . . ? C5 C4 C17 111.33(8) . . ? C17 C4 H4 108.7 . . ? C6 C5 C4 121.69(10) . . ? C6 C5 C9 120.94(10) . . ? C9 C5 C4 117.35(9) . . ? N1 C6 H6 118.8 . . ? C5 C6 N1 122.35(10) . . ? C5 C6 H6 118.8 . . ? O1 C7 C3 119.83(11) . . ? O1 C7 C8 120.07(11) . . ? C3 C7 C8 120.10(11) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C9 C5 119.85(10) . . ? O2 C9 C10 119.87(10) . . ? C5 C9 C10 120.26(10) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C1 118.40(10) . . ? C16 C11 C1 122.39(10) . . ? C16 C11 C12 119.18(11) . . ? C11 C12 H12 119.7 . . ? C13 C12 C11 120.60(11) . . ? C13 C12 H12 119.7 . . ? C12 C13 H13 120.1 . . ? C14 C13 C12 119.85(11) . . ? C14 C13 H13 120.1 . . ? C13 C14 H14 120.0 . . ? C13 C14 C15 119.98(12) . . ? C15 C14 H14 120.0 . . ? C14 C15 H15 119.9 . . ? C14 C15 C16 120.25(12) . . ? C16 C15 H15 119.9 . . ? C11 C16 H16 119.9 . . ? C15 C16 C11 120.14(11) . . ? C15 C16 H16 119.9 . . ? C18 C17 C4 120.37(9) . . ? C18 C17 C22 118.64(10) . . ? C22 C17 C4 120.91(9) . . ? C17 C18 H18 119.4 . . ? C19 C18 C17 121.10(10) . . ? C19 C18 H18 119.4 . . ? C18 C19 H19 120.8 . . ? C20 C19 C18 118.48(10) . . ? C20 C19 H19 120.8 . . ? C19 C20 N2 118.61(10) . . ? C19 C20 C21 122.28(10) . . ? C21 C20 N2 119.10(10) . . ? C20 C21 H21 120.8 . . ? C20 C21 C22 118.33(10) . . ? C22 C21 H21 120.8 . . ? C17 C22 H22 119.4 . . ? C21 C22 C17 121.13(10) . . ? C21 C22 H22 119.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 C11 -84.78(13) . . . . ? N1 C1 C11 C16 15.62(16) . . . . ? #===END data_\b-4a _database_code_depnum_ccdc_archive 'CCDC 869481' #TrackingRef '- PRG.cif' _audit_creation_date 2011-11-30 _audit_creation_method ; Olex2 1.1-beta (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; 1,1'-(1-Benzyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-diyl)diethanone ; _chemical_formula_moiety 'C22 H20 N2 O4' _chemical_formula_sum 'C22 H20 N2 O4' _chemical_formula_weight 376.40 _chemical_melting_point 457.7(5) 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 Monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 8.5606(5) _cell_length_b 21.0536(10) _cell_length_c 10.9717(7) _cell_angle_alpha 90.00 _cell_angle_beta 110.968(10) _cell_angle_gamma 90.00 _cell_volume 1846.5(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 4689 _cell_measurement_temperature 120 _cell_measurement_theta_max 29.95 _cell_measurement_theta_min 2.21 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_T_max 0.8622 _exptl_absorpt_correction_T_min 0.7285 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. R(int) was 0.0668 before and 0.0578 after correction. The Ratio of minimum to maximum transmission is 0.8449. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'irregular block' _exptl_crystal_F_000 792 _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.13 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 3 sets of \w scans each set at different \f and/or 2\q angles and each scan (5 s exposure) covering -0.3\% in \w. The crystal to detector distance was 4.85 cm. ; _diffrn_reflns_av_R_equivalents 0.0401 _diffrn_reflns_av_unetI/netI 0.0343 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 19286 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 1.93 _diffrn_ambient_temperature 120 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'sealed X-ray tube' _diffrn_source_current 35.0 _diffrn_source_power 1.75 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _reflns_number_gt 3243 _reflns_number_total 4234 _reflns_threshold_expression I>2\s(I) _computing_cell_refinement 'SAINT v7.46A (Bruker, 2008)' _computing_data_collection 'SMART v5.630 (Bruker, 2003)' _computing_data_reduction 'SAINT v7.46A (Bruker, 2008)' _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 "'XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122" _refine_diff_density_max 0.320 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.050 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 257 _refine_ls_number_reflns 4234 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0447 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0610P)^2^+0.6647P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1125 _refine_ls_wR_factor_ref 0.1258 _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. Methyl groups were refined as rigid bodies rotating around C---C bonds, with a common refined U for three H atoms. Other H atoms: riding model. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.16092(15) 0.69505(5) 0.81580(12) 0.0317(3) Uani 1 1 d . . . O2 O 0.68837(15) 0.56416(6) 0.94739(11) 0.0314(3) Uani 1 1 d . . . O3 O -0.01745(15) 0.37507(6) 0.62289(12) 0.0352(3) Uani 1 1 d . . . O4 O 0.06997(15) 0.37859(5) 0.46063(12) 0.0331(3) Uani 1 1 d . . . N1 N 0.51808(16) 0.69707(6) 0.57529(12) 0.0234(3) Uani 1 1 d . . . N2 N 0.06211(16) 0.40021(6) 0.56239(13) 0.0266(3) Uani 1 1 d . . . C1 C 0.5572(2) 0.72308(7) 0.46583(15) 0.0260(3) Uani 1 1 d . . . H1A H 0.6766 0.7356 0.4974 0.031 Uiso 1 1 d R . . H1B H 0.4896 0.7619 0.4337 0.031 Uiso 1 1 d R . . C2 C 0.37101(19) 0.71272(7) 0.59229(14) 0.0230(3) Uani 1 1 d . . . H2 H 0.2993 0.7433 0.5359 0.028 Uiso 1 1 d R . . C3 C 0.32527(18) 0.68613(7) 0.68646(14) 0.0224(3) Uani 1 1 d . . . C4 C 0.42307(18) 0.63047(7) 0.76639(14) 0.0214(3) Uani 1 1 d . . . H4 H 0.4307 0.6360 0.8589 0.026 Uiso 1 1 calc R . . C5 C 0.59861(18) 0.62995(7) 0.76350(14) 0.0212(3) Uani 1 1 d . . . C6 C 0.63285(19) 0.65983(7) 0.66715(14) 0.0227(3) Uani 1 1 d . . . H6 H 0.7409 0.6548 0.6626 0.027 Uiso 1 1 d R . . C7 C 0.18416(19) 0.71213(7) 0.71684(15) 0.0254(3) Uani 1 1 d . . . C8 C 0.0717(2) 0.76138(8) 0.62767(18) 0.0318(4) Uani 1 1 d . . . H8A H -0.0206 0.7714 0.6576 0.050(4) Uiso 1 1 d R . . H8B H 0.0264 0.7447 0.5385 0.050(4) Uiso 1 1 d R . . H8C H 0.1361 0.8001 0.6291 0.050(4) Uiso 1 1 d R . . C9 C 0.72562(19) 0.59240(7) 0.86380(14) 0.0236(3) Uani 1 1 d . . . C10 C 0.9011(2) 0.58850(9) 0.86299(17) 0.0332(4) Uani 1 1 d . . . H10A H 0.9515 0.6309 0.8771 0.050(3) Uiso 1 1 d R . . H10B H 0.8979 0.5721 0.7786 0.050(3) Uiso 1 1 d R . . H10C H 0.9679 0.5600 0.9328 0.050(3) Uiso 1 1 d R . . C11 C 0.5242(2) 0.67690(7) 0.35337(14) 0.0256(3) Uani 1 1 d . . . C12 C 0.6245(2) 0.67912(8) 0.27784(15) 0.0304(4) Uani 1 1 d . . . H12 H 0.7133 0.7090 0.2982 0.037 Uiso 1 1 d R . . C13 C 0.5960(2) 0.63817(9) 0.17323(16) 0.0356(4) Uani 1 1 d . . . H13 H 0.6644 0.6404 0.1217 0.043 Uiso 1 1 d R . . C14 C 0.4679(2) 0.59399(9) 0.14377(16) 0.0387(4) Uani 1 1 d . . . H14 H 0.4494 0.5654 0.0730 0.046 Uiso 1 1 d R . . C15 C 0.3672(2) 0.59175(9) 0.21763(17) 0.0371(4) Uani 1 1 d . . . H15 H 0.2790 0.5616 0.1972 0.044 Uiso 1 1 d R . . C16 C 0.3940(2) 0.63342(8) 0.32221(16) 0.0300(4) Uani 1 1 d . . . H16 H 0.3231 0.6320 0.3719 0.036 Uiso 1 1 d R . . C17 C 0.33107(18) 0.56830(7) 0.71420(14) 0.0211(3) Uani 1 1 d . . . C18 C 0.34060(19) 0.54012(7) 0.60199(15) 0.0243(3) Uani 1 1 d . . . H18 H 0.4087 0.5588 0.5598 0.029 Uiso 1 1 d R . . C19 C 0.2518(2) 0.48517(7) 0.55134(14) 0.0250(3) Uani 1 1 d . . . H19 H 0.2574 0.4662 0.4744 0.030 Uiso 1 1 d R . . C20 C 0.15508(18) 0.45863(7) 0.61529(15) 0.0228(3) Uani 1 1 d . . . C21 C 0.14534(19) 0.48458(7) 0.72816(15) 0.0251(3) Uani 1 1 d . . . H21 H 0.0793 0.4651 0.7712 0.030 Uiso 1 1 d R . . C22 C 0.23435(19) 0.53975(7) 0.77716(15) 0.0240(3) Uani 1 1 d . . . H22 H 0.2290 0.5583 0.8546 0.029 Uiso 1 1 d 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 O1 0.0321(6) 0.0311(6) 0.0368(6) -0.0030(5) 0.0183(5) 0.0005(5) O2 0.0328(6) 0.0371(7) 0.0257(6) 0.0076(5) 0.0122(5) 0.0057(5) O3 0.0335(6) 0.0303(6) 0.0420(7) 0.0002(5) 0.0138(5) -0.0093(5) O4 0.0345(6) 0.0283(6) 0.0331(6) -0.0083(5) 0.0077(5) -0.0050(5) N1 0.0286(7) 0.0220(6) 0.0197(6) 0.0009(5) 0.0089(5) 0.0010(5) N2 0.0222(6) 0.0231(6) 0.0306(7) 0.0009(5) 0.0048(5) 0.0002(5) C1 0.0327(8) 0.0237(8) 0.0222(7) 0.0024(6) 0.0105(6) 0.0001(6) C2 0.0249(7) 0.0199(7) 0.0210(7) -0.0031(5) 0.0042(6) 0.0008(6) C3 0.0227(7) 0.0192(7) 0.0226(7) -0.0035(5) 0.0048(6) -0.0018(5) C4 0.0225(7) 0.0213(7) 0.0199(7) -0.0011(5) 0.0071(6) -0.0008(6) C5 0.0225(7) 0.0199(7) 0.0203(7) -0.0035(5) 0.0066(6) -0.0008(5) C6 0.0236(7) 0.0212(7) 0.0225(7) -0.0026(5) 0.0072(6) -0.0011(6) C7 0.0230(7) 0.0212(7) 0.0306(8) -0.0063(6) 0.0080(6) -0.0029(6) C8 0.0255(8) 0.0260(8) 0.0409(9) -0.0026(7) 0.0082(7) 0.0018(6) C9 0.0269(8) 0.0235(7) 0.0207(7) -0.0022(6) 0.0088(6) 0.0006(6) C10 0.0251(8) 0.0409(10) 0.0321(9) 0.0090(7) 0.0085(7) 0.0060(7) C11 0.0298(8) 0.0243(7) 0.0199(7) 0.0051(6) 0.0056(6) 0.0076(6) C12 0.0357(9) 0.0297(8) 0.0256(8) 0.0084(6) 0.0108(7) 0.0093(7) C13 0.0462(10) 0.0385(10) 0.0237(8) 0.0079(7) 0.0145(7) 0.0187(8) C14 0.0504(11) 0.0381(10) 0.0200(8) -0.0006(7) 0.0033(8) 0.0174(8) C15 0.0387(10) 0.0333(9) 0.0287(8) -0.0029(7) -0.0008(7) 0.0036(7) C16 0.0321(9) 0.0310(8) 0.0250(8) 0.0018(6) 0.0079(7) 0.0036(7) C17 0.0204(7) 0.0198(7) 0.0207(7) 0.0008(5) 0.0045(6) 0.0016(5) C18 0.0276(8) 0.0227(7) 0.0234(7) 0.0001(6) 0.0102(6) -0.0017(6) C19 0.0291(8) 0.0234(7) 0.0209(7) -0.0023(6) 0.0068(6) -0.0004(6) C20 0.0201(7) 0.0182(7) 0.0257(7) -0.0001(5) 0.0027(6) 0.0007(5) C21 0.0232(7) 0.0242(7) 0.0289(8) 0.0030(6) 0.0105(6) 0.0001(6) C22 0.0252(7) 0.0249(7) 0.0227(7) 0.0005(6) 0.0096(6) 0.0024(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 C7 1.2258(19) . ? O2 C9 1.2271(18) . ? O3 N2 1.2281(18) . ? O4 N2 1.2295(18) . ? N1 C1 1.4637(19) . ? N1 C2 1.377(2) . ? N1 C6 1.3737(19) . ? N2 C20 1.4672(19) . ? C1 H1A 0.9902 . ? C1 H1B 0.9901 . ? C1 C11 1.516(2) . ? C2 H2 0.9498 . ? C2 C3 1.350(2) . ? C3 C4 1.522(2) . ? C3 C7 1.469(2) . ? C4 H4 1.0000 . ? C4 C5 1.514(2) . ? C4 C17 1.5292(19) . ? C5 C6 1.349(2) . ? C5 C9 1.470(2) . ? C6 H6 0.9501 . ? C7 C8 1.512(2) . ? C8 H8A 0.9806 . ? C8 H8B 0.9795 . ? C8 H8C 0.9805 . ? C9 C10 1.508(2) . ? C10 H10A 0.9798 . ? C10 H10B 0.9798 . ? C10 H10C 0.9801 . ? C11 C12 1.391(2) . ? C11 C16 1.388(2) . ? C12 H12 0.9499 . ? C12 C13 1.386(2) . ? C13 H13 0.9500 . ? C13 C14 1.385(3) . ? C14 H14 0.9503 . ? C14 C15 1.379(3) . ? C15 H15 0.9500 . ? C15 C16 1.397(2) . ? C16 H16 0.9500 . ? C17 C18 1.395(2) . ? C17 C22 1.390(2) . ? C18 H18 0.9499 . ? C18 C19 1.386(2) . ? C19 H19 0.9500 . ? C19 C20 1.381(2) . ? C20 C21 1.383(2) . ? C21 H21 0.9500 . ? C21 C22 1.388(2) . ? C22 H22 0.9502 . ? 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 N1 C1 120.69(12) . . ? C6 N1 C1 120.12(13) . . ? C6 N1 C2 119.06(13) . . ? O3 N2 O4 123.53(14) . . ? O3 N2 C20 118.34(13) . . ? O4 N2 C20 118.12(13) . . ? N1 C1 H1A 108.9 . . ? N1 C1 H1B 108.9 . . ? N1 C1 C11 113.40(13) . . ? H1A C1 H1B 107.7 . . ? C11 C1 H1A 108.9 . . ? C11 C1 H1B 108.9 . . ? N1 C2 H2 118.8 . . ? C3 C2 N1 122.26(14) . . ? C3 C2 H2 118.9 . . ? C2 C3 C4 120.64(14) . . ? C2 C3 C7 120.40(14) . . ? C7 C3 C4 118.92(13) . . ? C3 C4 H4 108.5 . . ? C3 C4 C17 109.86(11) . . ? C5 C4 C3 109.80(12) . . ? C5 C4 H4 108.5 . . ? C5 C4 C17 111.59(12) . . ? C17 C4 H4 108.5 . . ? C6 C5 C4 120.56(13) . . ? C6 C5 C9 121.82(14) . . ? C9 C5 C4 117.50(13) . . ? N1 C6 H6 118.6 . . ? C5 C6 N1 122.82(14) . . ? C5 C6 H6 118.6 . . ? O1 C7 C3 119.92(14) . . ? O1 C7 C8 120.45(14) . . ? C3 C7 C8 119.60(14) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C7 C8 H8C 109.6 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.4 . . ? H8B C8 H8C 109.4 . . ? O2 C9 C5 119.98(14) . . ? O2 C9 C10 120.26(14) . . ? C5 C9 C10 119.76(13) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.4 . . ? C12 C11 C1 119.23(15) . . ? C16 C11 C1 121.54(15) . . ? C16 C11 C12 119.22(15) . . ? C11 C12 H12 119.7 . . ? C13 C12 C11 120.63(17) . . ? C13 C12 H12 119.7 . . ? C12 C13 H13 120.0 . . ? C14 C13 C12 120.08(17) . . ? C14 C13 H13 119.9 . . ? C13 C14 H14 120.2 . . ? C15 C14 C13 119.67(16) . . ? C15 C14 H14 120.1 . . ? C14 C15 H15 119.7 . . ? C14 C15 C16 120.53(18) . . ? C16 C15 H15 119.7 . . ? C11 C16 C15 119.86(17) . . ? C11 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C18 C17 C4 120.63(13) . . ? C22 C17 C4 120.16(13) . . ? C22 C17 C18 119.20(14) . . ? C17 C18 H18 119.6 . . ? C19 C18 C17 120.78(14) . . ? C19 C18 H18 119.6 . . ? C18 C19 H19 120.8 . . ? C20 C19 C18 118.45(14) . . ? C20 C19 H19 120.8 . . ? C19 C20 N2 118.51(13) . . ? C19 C20 C21 122.31(14) . . ? C21 C20 N2 119.17(14) . . ? C20 C21 H21 120.8 . . ? C20 C21 C22 118.48(14) . . ? C22 C21 H21 120.8 . . ? C17 C22 H22 119.6 . . ? C21 C22 C17 120.76(14) . . ? C21 C22 H22 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 C11 -100.79(16) . . . . ? N1 C1 C11 C16 33.5(2) . . . . ? #===END data_4d _database_code_depnum_ccdc_archive 'CCDC 869482' #TrackingRef '- PRG.cif' _audit_creation_date 2011-11-30 _audit_creation_method ; Olex2 1.1-beta (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; 1,1'-(1-Benzyl-4-ethyl-1,4-dihydropyridine-3,5-diyl)diethanone ; _chemical_formula_moiety 'C18 H21 N O2' _chemical_formula_sum 'C18 H21 N O2' _chemical_formula_weight 283.36 _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 0.0033 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 monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.3258(9) _cell_length_b 14.5225(14) _cell_length_c 11.5197(10) _cell_angle_alpha 90.00 _cell_angle_beta 98.448(19) _cell_angle_gamma 90.00 _cell_volume 1543.2(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 3132 _cell_measurement_temperature 120 _cell_measurement_theta_max 23.528 _cell_measurement_theta_min 2.629 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_T_max 0.8620 _exptl_absorpt_correction_T_min 0.7627 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. R(int) was 0.1065 before and 0.0748 after correction. The Ratio of minimum to maximum transmission is 0.8848. The \l/2 correction factor is 0.0015. Non-merohedrally twinned crystal (no correction applied). ; _exptl_crystal_colour 'light yellow' _exptl_crystal_density_diffrn 1.220 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description trapetsoid _exptl_crystal_F_000 608 _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of \w scans each set at different \f and/or 2\q angles and each scan (30 s exposure) covering -0.300\% degrees in \w. The crystal to detector distance was 4.85 cm. ; _diffrn_reflns_av_R_equivalents 0.0748 _diffrn_reflns_av_unetI/netI 0.0391 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 23205 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.27 _diffrn_ambient_temperature 120 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'sealed X-ray tube' _diffrn_source_current 10.0 _diffrn_source_power 0.3 _diffrn_source_target Mo _diffrn_source_voltage 30.0 _diffrn_standards_number 0 _reflns_number_gt 1863 _reflns_number_total 2717 _reflns_threshold_expression I>2\s(I) _computing_cell_refinement 'SAINT v7.46A (Bruker, 2008)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v7.46A (Bruker, 2008)' _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 'XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122' _refine_diff_density_max 0.175 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.039 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 195 _refine_ls_number_reflns 2717 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0746 _refine_ls_R_factor_gt 0.0402 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0369P)^2^+0.6522P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0854 _refine_ls_wR_factor_ref 0.1020 _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. Methyl groups C(8)H~3~ and C(18)H~3~ were refined as rigid bodies rotating around C---C bonds, with a common refined U for three H atoms. Other H atoms: riding model. Methyl group C(10)H~3~ is rotationally disordered between two opposite orientations with occupancies 0.67 and 0.33. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.57288(15) 0.33452(9) 0.20217(11) 0.0334(4) Uani 1 1 d . . . O2 O 0.17990(14) 0.09118(9) 0.21670(11) 0.0302(3) Uani 1 1 d . . . N1 N 0.40119(17) 0.25040(11) 0.55335(13) 0.0260(4) Uani 1 1 d . . . C1 C 0.3856(2) 0.27723(13) 0.67289(16) 0.0275(4) Uani 1 1 d . . . H1A H 0.2811 0.2778 0.6801 0.033 Uiso 1 1 calc R . . H1B H 0.4222 0.3409 0.6863 0.033 Uiso 1 1 calc R . . C2 C 0.4851(2) 0.30129(13) 0.48853(16) 0.0254(4) Uani 1 1 d . . . H2 H 0.5396 0.3512 0.5256 0.030 Uiso 1 1 d R . . C3 C 0.4937(2) 0.28392(13) 0.37523(16) 0.0243(4) Uani 1 1 d . . . C4 C 0.4197(2) 0.20033(13) 0.31336(16) 0.0252(4) Uani 1 1 d . . . H4 H 0.3685 0.2210 0.2353 0.030 Uiso 1 1 d R . . C5 C 0.3066(2) 0.16273(13) 0.38313(15) 0.0239(4) Uani 1 1 d . . . C6 C 0.3072(2) 0.18591(13) 0.49644(16) 0.0255(4) Uani 1 1 d . . . H6 H 0.2401 0.1567 0.5390 0.031 Uiso 1 1 d R . . C7 C 0.5696(2) 0.34775(13) 0.30753(16) 0.0269(4) Uani 1 1 d . . . C8 C 0.6399(2) 0.43333(14) 0.36490(18) 0.0360(5) Uani 1 1 d . . . H8A H 0.7065 0.4594 0.3152 0.049(4) Uiso 1 1 d R . . H8B H 0.6940 0.4174 0.4418 0.049(4) Uiso 1 1 d R . . H8C H 0.5650 0.4787 0.3750 0.049(4) Uiso 1 1 d R . . C9 C 0.1934(2) 0.10201(13) 0.32408(16) 0.0259(4) Uani 1 1 d . . . C10 C 0.0929(2) 0.05160(15) 0.39349(18) 0.0351(5) Uani 1 1 d . . . H10A H 0.0126 0.0248 0.3396 0.048(6) Uiso 0.67 1 d PR A 1 H10B H 0.0544 0.0948 0.4466 0.048(6) Uiso 0.67 1 d PR A 1 H10C H 0.1463 0.0024 0.4394 0.048(6) Uiso 0.67 1 d PR A 1 H10D H 0.0917 -0.0134 0.3706 0.048(6) Uiso 0.33 1 d PR A 2 H10E H -0.0029 0.0770 0.3772 0.048(6) Uiso 0.33 1 d PR A 2 H10F H 0.1264 0.0577 0.4760 0.048(6) Uiso 0.33 1 d PR A 2 C11 C 0.4630(2) 0.21632(13) 0.76785(16) 0.0252(4) Uani 1 1 d . . . C12 C 0.4252(2) 0.22350(15) 0.87958(17) 0.0356(5) Uani 1 1 d . . . H12 H 0.3507 0.2651 0.8931 0.043 Uiso 1 1 d R . . C13 C 0.4935(2) 0.17159(17) 0.97117(18) 0.0434(6) Uani 1 1 d . . . H13 H 0.4666 0.1777 1.0472 0.052 Uiso 1 1 d R . . C14 C 0.6010(3) 0.11082(15) 0.95250(19) 0.0419(6) Uani 1 1 d . . . H14 H 0.6473 0.0743 1.0155 0.050 Uiso 1 1 d R . . C15 C 0.6415(2) 0.10274(14) 0.8430(2) 0.0401(5) Uani 1 1 d . . . H15 H 0.7165 0.0613 0.8304 0.048 Uiso 1 1 d R . . C16 C 0.5721(2) 0.15574(14) 0.74997(18) 0.0327(5) Uani 1 1 d . . . H16 H 0.5998 0.1500 0.6742 0.039 Uiso 1 1 d R . . C17 C 0.5295(2) 0.12464(14) 0.29151(17) 0.0306(5) Uani 1 1 d . . . H17A H 0.4762 0.0742 0.2461 0.037 Uiso 1 1 d R . . H17B H 0.5983 0.1509 0.2426 0.037 Uiso 1 1 d R . . C18 C 0.6153(2) 0.08424(15) 0.40171(19) 0.0398(5) Uani 1 1 d . . . H18A H 0.6827 0.0377 0.3801 0.054(4) Uiso 1 1 d R . . H18B H 0.5487 0.0556 0.4494 0.054(4) Uiso 1 1 d R . . H18C H 0.6700 0.1333 0.4469 0.054(4) Uiso 1 1 d 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 O1 0.0400(9) 0.0334(8) 0.0281(8) 0.0040(6) 0.0099(6) -0.0003(6) O2 0.0329(8) 0.0318(8) 0.0247(7) -0.0035(6) 0.0001(6) 0.0009(6) N1 0.0263(9) 0.0316(9) 0.0200(8) -0.0011(7) 0.0028(7) -0.0031(7) C1 0.0281(11) 0.0319(11) 0.0224(10) -0.0012(8) 0.0038(8) 0.0014(9) C2 0.0235(10) 0.0251(10) 0.0267(10) 0.0022(8) 0.0008(8) -0.0009(8) C3 0.0240(10) 0.0248(10) 0.0238(10) 0.0025(8) 0.0023(8) 0.0016(8) C4 0.0265(10) 0.0275(10) 0.0214(10) 0.0017(8) 0.0026(8) -0.0006(8) C5 0.0236(10) 0.0250(10) 0.0228(10) 0.0033(8) 0.0023(8) 0.0005(8) C6 0.0232(10) 0.0282(10) 0.0250(10) 0.0045(8) 0.0026(8) -0.0022(8) C7 0.0267(11) 0.0263(10) 0.0279(11) 0.0028(9) 0.0041(8) 0.0029(8) C8 0.0421(13) 0.0298(11) 0.0371(12) 0.0042(9) 0.0089(10) -0.0063(9) C9 0.0248(10) 0.0252(10) 0.0268(11) 0.0016(8) 0.0002(8) 0.0042(8) C10 0.0324(12) 0.0389(12) 0.0328(12) 0.0020(10) 0.0011(9) -0.0086(10) C11 0.0258(10) 0.0255(10) 0.0233(10) -0.0028(8) 0.0003(8) -0.0040(8) C12 0.0325(12) 0.0485(13) 0.0257(11) 0.0017(10) 0.0039(9) 0.0025(10) C13 0.0441(14) 0.0600(16) 0.0257(11) 0.0065(11) 0.0034(10) -0.0033(12) C14 0.0495(14) 0.0361(12) 0.0349(13) 0.0074(10) -0.0112(10) -0.0042(11) C15 0.0417(13) 0.0282(11) 0.0462(13) -0.0060(10) -0.0082(10) 0.0055(10) C16 0.0348(11) 0.0335(11) 0.0283(11) -0.0077(9) -0.0004(9) 0.0008(9) C17 0.0303(11) 0.0300(11) 0.0328(11) -0.0022(9) 0.0092(9) -0.0019(9) C18 0.0368(13) 0.0366(12) 0.0478(13) 0.0087(11) 0.0120(10) 0.0060(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 O1 C7 1.234(2) . ? O2 C9 1.235(2) . ? N1 C1 1.459(2) . ? N1 C2 1.374(2) . ? N1 C6 1.381(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C1 C11 1.506(3) . ? C2 H2 0.9500 . ? C2 C3 1.343(3) . ? C3 C4 1.521(3) . ? C3 C7 1.460(3) . ? C4 H4 1.0000 . ? C4 C5 1.519(3) . ? C4 C17 1.548(3) . ? C5 C6 1.347(3) . ? C5 C9 1.464(3) . ? C6 H6 0.9499 . ? C7 C8 1.511(3) . ? C8 H8A 0.9799 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.508(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9799 . ? C10 H10D 0.9800 . ? C10 H10E 0.9600 . ? C10 H10F 0.9600 . ? C11 C12 1.387(3) . ? C11 C16 1.383(3) . ? C12 H12 0.9501 . ? C12 C13 1.375(3) . ? C13 H13 0.9501 . ? C13 C14 1.376(3) . ? C14 H14 0.9501 . ? C14 C15 1.374(3) . ? C15 H15 0.9500 . ? C15 C16 1.398(3) . ? C16 H16 0.9500 . ? C17 H17A 0.9900 . ? C17 H17B 0.9899 . ? C17 C18 1.516(3) . ? C18 H18A 0.9801 . ? C18 H18B 0.9803 . ? C18 H18C 0.9801 . ? 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 N1 C1 120.88(16) . . ? C2 N1 C6 118.64(15) . . ? C6 N1 C1 118.99(16) . . ? N1 C1 H1A 108.5 . . ? N1 C1 H1B 108.5 . . ? N1 C1 C11 115.15(16) . . ? H1A C1 H1B 107.5 . . ? C11 C1 H1A 108.5 . . ? C11 C1 H1B 108.5 . . ? N1 C2 H2 118.4 . . ? C3 C2 N1 123.18(17) . . ? C3 C2 H2 118.4 . . ? C2 C3 C4 121.17(17) . . ? C2 C3 C7 120.19(17) . . ? C7 C3 C4 118.59(16) . . ? C3 C4 H4 107.8 . . ? C3 C4 C17 112.22(16) . . ? C5 C4 C3 109.97(15) . . ? C5 C4 H4 107.8 . . ? C5 C4 C17 110.99(15) . . ? C17 C4 H4 107.8 . . ? C6 C5 C4 121.24(17) . . ? C6 C5 C9 120.04(17) . . ? C9 C5 C4 118.70(15) . . ? N1 C6 H6 118.6 . . ? C5 C6 N1 122.77(18) . . ? C5 C6 H6 118.6 . . ? O1 C7 C3 120.72(18) . . ? O1 C7 C8 119.10(17) . . ? C3 C7 C8 120.13(16) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C9 C5 120.17(17) . . ? O2 C9 C10 119.31(17) . . ? C5 C9 C10 120.52(16) . . ? C9 C10 H10A 109.4 . . ? C9 C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? C9 C10 H10D 108.0 . . ? C9 C10 H10E 110.0 . . ? C9 C10 H10F 110.1 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? H10D C10 H10E 110.2 . . ? H10D C10 H10F 110.2 . . ? H10E C10 H10F 108.5 . . ? C12 C11 C1 118.02(17) . . ? C16 C11 C1 123.37(17) . . ? C16 C11 C12 118.59(18) . . ? C11 C12 H12 119.4 . . ? C13 C12 C11 121.2(2) . . ? C13 C12 H12 119.4 . . ? C12 C13 H13 120.1 . . ? C12 C13 C14 119.9(2) . . ? C14 C13 H13 120.1 . . ? C13 C14 H14 119.9 . . ? C15 C14 C13 120.2(2) . . ? C15 C14 H14 119.9 . . ? C14 C15 H15 120.1 . . ? C14 C15 C16 119.9(2) . . ? C16 C15 H15 120.1 . . ? C11 C16 C15 120.26(19) . . ? C11 C16 H16 119.8 . . ? C15 C16 H16 119.9 . . ? C4 C17 H17A 108.6 . . ? C4 C17 H17B 108.6 . . ? H17A C17 H17B 107.6 . . ? C18 C17 C4 114.78(16) . . ? C18 C17 H17A 108.6 . . ? C18 C17 H17B 108.6 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? #===END data_4e _database_code_depnum_ccdc_archive 'CCDC 869483' #TrackingRef '- PRG.cif' _audit_creation_date 2012-02-03 _audit_creation_method ; Olex2 1.1-beta (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; 1,1'-(1-Benzyl-4-(dimethoxymethyl)-1,4-dihydropyridine-3,5-diyl)diethanone ; _chemical_formula_moiety 'C19 H23 N O4' _chemical_formula_sum 'C19 H23 N O4' _chemical_formula_weight 329.38 _chemical_melting_point 411 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 61 _space_group_name_H-M_alt 'P b c a' _space_group_name_Hall '-P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 '-x-1/2, y-1/2, z' 8 'x, -y-1/2, z-1/2' _cell_length_a 12.0102(2) _cell_length_b 13.7886(3) _cell_length_c 20.7109(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3429.80(11) _cell_formula_units_Z 8 _cell_measurement_reflns_used 8110 _cell_measurement_temperature 120 _cell_measurement_theta_max 29.403 _cell_measurement_theta_min 2.597 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1408 _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.1 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of \w scans each set at different \f and/or 2\q angles and each scan (10 s exposure) covering -0.3\% in \w. The crystal to detector distance was 4.84 cm. ; _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_unetI/netI 0.0219 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 30328 _diffrn_reflns_theta_full 25.03 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_min 1.97 _diffrn_ambient_temperature 120 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'sealed X-ray tube' _diffrn_source_current 35.0 _diffrn_source_power 1.75 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _reflns_number_gt 2384 _reflns_number_total 3028 _reflns_threshold_expression I>2\s(I) _computing_cell_refinement 'SAINT v7.46A (Bruker, 2008)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v7.46A (Bruker, 2008)' _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 ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.177 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.037 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 221 _refine_ls_number_reflns 3028 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0355 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0496P)^2^+0.8379P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0877 _refine_ls_wR_factor_ref 0.0941 _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. Methyl groups were refined as rigid bodies rotating around C---C bonds, other H atoms in riding model. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 -0.02868(9) 0.43867(8) 0.39203(7) 0.0442(3) Uani 1 1 d . . . O2 O 0.03596(9) 0.72338(8) 0.25786(5) 0.0321(3) Uani 1 1 d . . . O3 O 0.08861(8) 0.73604(7) 0.40478(5) 0.0271(2) Uani 1 1 d . . . O4 O 0.22472(8) 0.63176(7) 0.43586(5) 0.0254(2) Uani 1 1 d . . . N1 N 0.32814(9) 0.51143(9) 0.31102(6) 0.0250(3) Uani 1 1 d . . . C1 C 0.44232(12) 0.47974(11) 0.29905(7) 0.0282(3) Uani 1 1 d . . . H1A H 0.4661 0.5047 0.2564 0.034 Uiso 1 1 calc R . . H1B H 0.4434 0.4080 0.2968 0.034 Uiso 1 1 calc R . . C2 C 0.25349(12) 0.45058(10) 0.34098(6) 0.0237(3) Uani 1 1 d . . . H2 H 0.2767 0.3868 0.3520 0.028 Uiso 1 1 calc R . . C3 C 0.14863(11) 0.47808(10) 0.35528(6) 0.0223(3) Uani 1 1 d . . . C4 C 0.11381(11) 0.58266(10) 0.34687(7) 0.0226(3) Uani 1 1 d . . . H4 H 0.0352 0.5833 0.3310 0.027 Uiso 1 1 calc R . . C5 C 0.18573(12) 0.63063(10) 0.29628(7) 0.0232(3) Uani 1 1 d . . . C6 C 0.28936(12) 0.59706(10) 0.28506(7) 0.0244(3) Uani 1 1 d . . . H6 H 0.3376 0.6339 0.2582 0.029 Uiso 1 1 calc R . . C7 C 0.06544(12) 0.40967(11) 0.37994(7) 0.0272(3) Uani 1 1 d . . . C8 C 0.09251(13) 0.30427(11) 0.38848(8) 0.0335(4) Uani 1 1 d . . . H8A H 0.0449 0.2767 0.4223 0.050 Uiso 1 1 calc R . . H8B H 0.1708 0.2974 0.4010 0.050 Uiso 1 1 calc R . . H8C H 0.0795 0.2698 0.3478 0.050 Uiso 1 1 calc R . . C9 C 0.13663(13) 0.70654(10) 0.25553(7) 0.0264(3) Uani 1 1 d . . . C10 C 0.20836(14) 0.76123(12) 0.20809(8) 0.0356(4) Uani 1 1 d . . . H10A H 0.2221 0.7206 0.1701 0.053 Uiso 1 1 calc R . . H10B H 0.2795 0.7778 0.2285 0.053 Uiso 1 1 calc R . . H10C H 0.1701 0.8208 0.1949 0.053 Uiso 1 1 calc R . . C11 C 0.52577(12) 0.51203(10) 0.34915(7) 0.0247(3) Uani 1 1 d . . . C12 C 0.63802(12) 0.49206(11) 0.33800(8) 0.0293(3) Uani 1 1 d . . . H12 H 0.6595 0.4599 0.2994 0.035 Uiso 1 1 calc R . . C13 C 0.71812(13) 0.51837(12) 0.38235(8) 0.0364(4) Uani 1 1 d . . . H13 H 0.7944 0.5048 0.3741 0.044 Uiso 1 1 calc R . . C14 C 0.68723(14) 0.56469(12) 0.43905(9) 0.0382(4) Uani 1 1 d . . . H14 H 0.7421 0.5824 0.4699 0.046 Uiso 1 1 calc R . . C15 C 0.57674(14) 0.58489(12) 0.45040(8) 0.0357(4) Uani 1 1 d . . . H15 H 0.5557 0.6169 0.4891 0.043 Uiso 1 1 calc R . . C16 C 0.49574(13) 0.55887(11) 0.40576(8) 0.0293(4) Uani 1 1 d . . . H16 H 0.4197 0.5732 0.4140 0.035 Uiso 1 1 calc R . . C17 C 0.11704(12) 0.63639(10) 0.41178(7) 0.0227(3) Uani 1 1 d . . . H17 H 0.0646 0.6047 0.4428 0.027 Uiso 1 1 calc R . . C18 C -0.02830(13) 0.75156(12) 0.40540(8) 0.0361(4) Uani 1 1 d . . . H18A H -0.0616 0.7218 0.3670 0.054 Uiso 1 1 calc R . . H18B H -0.0436 0.8214 0.4053 0.054 Uiso 1 1 calc R . . H18C H -0.0603 0.7222 0.4443 0.054 Uiso 1 1 calc R . . C19 C 0.23240(13) 0.66445(12) 0.50133(7) 0.0322(4) Uani 1 1 d . . . H19A H 0.2228 0.7350 0.5027 0.048 Uiso 1 1 calc R . . H19B H 0.3056 0.6474 0.5189 0.048 Uiso 1 1 calc R . . H19C H 0.1741 0.6334 0.5272 0.048 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 O1 0.0241(6) 0.0312(6) 0.0774(9) 0.0095(6) 0.0107(6) 0.0002(5) O2 0.0333(6) 0.0307(6) 0.0324(6) 0.0027(5) -0.0020(5) 0.0068(5) O3 0.0290(6) 0.0213(5) 0.0312(6) -0.0006(4) 0.0010(4) 0.0045(4) O4 0.0225(5) 0.0284(6) 0.0253(5) -0.0035(4) -0.0014(4) 0.0002(4) N1 0.0211(6) 0.0252(6) 0.0288(7) -0.0009(5) 0.0026(5) 0.0011(5) C1 0.0236(8) 0.0289(8) 0.0322(8) -0.0010(6) 0.0054(6) 0.0035(6) C2 0.0261(8) 0.0204(7) 0.0247(7) -0.0004(6) -0.0025(6) 0.0005(6) C3 0.0228(7) 0.0213(7) 0.0229(7) -0.0004(6) -0.0022(6) 0.0001(6) C4 0.0196(7) 0.0218(7) 0.0264(8) 0.0002(6) -0.0014(6) -0.0012(6) C5 0.0267(8) 0.0199(7) 0.0232(7) -0.0026(6) -0.0010(6) -0.0016(6) C6 0.0273(8) 0.0216(7) 0.0244(7) -0.0012(6) 0.0009(6) -0.0045(6) C7 0.0249(8) 0.0253(8) 0.0314(8) 0.0013(6) -0.0011(6) -0.0007(6) C8 0.0336(9) 0.0245(8) 0.0425(9) 0.0049(7) 0.0032(7) -0.0016(7) C9 0.0345(9) 0.0213(8) 0.0234(8) -0.0040(6) -0.0010(6) 0.0007(6) C10 0.0452(10) 0.0271(9) 0.0346(9) 0.0052(7) 0.0057(8) 0.0037(7) C11 0.0246(8) 0.0176(7) 0.0319(8) 0.0058(6) 0.0027(6) 0.0013(6) C12 0.0270(8) 0.0247(8) 0.0363(9) 0.0071(7) 0.0059(7) 0.0045(6) C13 0.0236(8) 0.0331(9) 0.0524(11) 0.0108(8) -0.0011(7) 0.0029(7) C14 0.0349(9) 0.0306(9) 0.0490(11) 0.0057(8) -0.0151(8) -0.0013(7) C15 0.0405(10) 0.0291(9) 0.0374(9) -0.0030(7) -0.0042(7) 0.0022(7) C16 0.0262(8) 0.0252(8) 0.0366(9) 0.0008(7) 0.0013(7) 0.0031(6) C17 0.0205(7) 0.0201(7) 0.0276(8) 0.0004(6) 0.0016(6) 0.0005(5) C18 0.0333(9) 0.0363(9) 0.0386(10) -0.0004(7) 0.0033(7) 0.0131(7) C19 0.0367(9) 0.0340(9) 0.0258(8) -0.0028(6) -0.0047(7) -0.0014(7) _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 C7 1.2249(18) . ? O2 C9 1.2320(18) . ? O3 C17 1.4232(16) . ? O3 C18 1.4204(18) . ? O4 C17 1.3876(17) . ? O4 C19 1.4318(17) . ? N1 C1 1.4605(18) . ? N1 C2 1.3758(18) . ? N1 C6 1.3785(19) . ? C1 C11 1.510(2) . ? C2 C3 1.348(2) . ? C3 C4 1.512(2) . ? C3 C7 1.466(2) . ? C4 C5 1.510(2) . ? C4 C17 1.5354(19) . ? C5 C6 1.348(2) . ? C5 C9 1.468(2) . ? C7 C8 1.500(2) . ? C9 C10 1.509(2) . ? C11 C12 1.395(2) . ? C11 C16 1.386(2) . ? C12 C13 1.379(2) . ? C13 C14 1.387(2) . ? C14 C15 1.376(2) . ? C15 C16 1.389(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 C18 O3 C17 112.44(11) . . ? C17 O4 C19 112.70(11) . . ? C2 N1 C1 120.40(12) . . ? C2 N1 C6 118.56(12) . . ? C6 N1 C1 120.48(12) . . ? N1 C1 C11 114.73(12) . . ? C3 C2 N1 122.43(13) . . ? C2 C3 C4 120.10(13) . . ? C2 C3 C7 122.16(13) . . ? C7 C3 C4 117.74(12) . . ? C3 C4 C17 110.64(11) . . ? C5 C4 C3 109.84(11) . . ? C5 C4 C17 112.43(11) . . ? C6 C5 C4 119.82(13) . . ? C6 C5 C9 121.10(13) . . ? C9 C5 C4 118.77(12) . . ? C5 C6 N1 122.60(13) . . ? O1 C7 C3 119.35(13) . . ? O1 C7 C8 119.49(14) . . ? C3 C7 C8 121.12(13) . . ? O2 C9 C5 120.40(13) . . ? O2 C9 C10 119.45(13) . . ? C5 C9 C10 120.09(13) . . ? C12 C11 C1 118.00(13) . . ? C16 C11 C1 123.09(13) . . ? C16 C11 C12 118.90(14) . . ? C13 C12 C11 120.80(15) . . ? C12 C13 C14 119.90(15) . . ? C15 C14 C13 119.72(15) . . ? C14 C15 C16 120.61(16) . . ? C11 C16 C15 120.07(14) . . ? O3 C17 C4 111.75(11) . . ? O4 C17 O3 107.74(11) . . ? O4 C17 C4 108.42(11) . . ? #===END data_4f _database_code_depnum_ccdc_archive 'CCDC 869484' #TrackingRef '- PRG.cif' _audit_creation_date 2012-02-06 _audit_creation_method ; Olex2 1.1-beta (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; 1,1'-(4-(4-Nitrophenyl)-1-phenyl-1,4-dihydropyridine-3,5-diyl)diethanone ; _chemical_formula_moiety 'C21 H18 N2 O4' _chemical_formula_sum 'C21 H18 N2 O4' _chemical_formula_weight 362.37 _chemical_melting_point 490.7(5) 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 triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 8.7082(6) _cell_length_b 10.1835(5) _cell_length_c 11.0221(8) _cell_angle_alpha 100.666(5) _cell_angle_beta 110.831(6) _cell_angle_gamma 97.843(5) _cell_volume 875.72(9) _cell_formula_units_Z 2 _cell_measurement_reflns_used 4458 _cell_measurement_temperature 120 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 29.97 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_T_min 0.8916 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, V1.171.35.10 (2011) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 380 _exptl_crystal_size_max 0.61 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.28 _exptl_special_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -89.00 -3.80 0.3000 3.0000 omega____ theta____ kappa____ phi______ frames - -20.4620 -57.0000 -90.0000 284 #__ type_ start__ end____ width___ exp.time_ 2 omega -1.20 48.00 0.3000 3.0000 omega____ theta____ kappa____ phi______ frames - -20.4620 57.0000 60.0000 164 #__ type_ start__ end____ width___ exp.time_ 3 omega -89.00 8.20 0.3000 3.0000 omega____ theta____ kappa____ phi______ frames - -20.4620 -77.0000 150.0000 324 #__ type_ start__ end____ width___ exp.time_ 4 omega -40.00 -13.00 0.3000 3.0000 omega____ theta____ kappa____ phi______ frames - -20.4620 57.0000 60.0000 90 #__ type_ start__ end____ width___ exp.time_ 5 omega 65.90 97.70 0.3000 3.0000 omega____ theta____ kappa____ phi______ frames - 21.0870 -179.0000 0.0000 106 #__ type_ start__ end____ width___ exp.time_ 6 omega 25.80 62.70 0.3000 3.0000 omega____ theta____ kappa____ phi______ frames - 21.0870 -100.0000 60.0000 123 #__ type_ start__ end____ width___ exp.time_ 7 omega -10.00 19.10 0.3000 3.0000 omega____ theta____ kappa____ phi______ frames - 21.0870 95.0000 -178.0000 97 #__ type_ start__ end____ width___ exp.time_ 8 omega -40.00 61.10 0.3000 3.0000 omega____ theta____ kappa____ phi______ frames - 21.0870 -19.0000 -30.0000 337 #__ type_ start__ end____ width___ exp.time_ 9 omega -93.00 3.90 0.3000 3.0000 omega____ theta____ kappa____ phi______ frames - -20.4620 -38.0000 0.0000 323 #__ type_ start__ end____ width___ exp.time_ 10 omega -60.00 30.00 0.3000 3.0000 omega____ theta____ kappa____ phi______ frames - -20.4620 95.0000 -71.0000 300 #__ type_ start__ end____ width___ exp.time_ 11 omega -97.00 -71.80 0.3000 3.0000 omega____ theta____ kappa____ phi______ frames - -20.4620 -179.0000 30.0000 84 #__ type_ start__ end____ width___ exp.time_ 12 omega 53.00 98.00 0.3000 3.0000 omega____ theta____ kappa____ phi______ frames - 21.0870 -179.0000 -90.0000 150 ; loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 0 1 0.1437 1 0 -1 0.1437 0 1 0 0.1405 0 -1 0 0.1405 0 0 1 0.1965 0 0 -1 0.1831 0 -1 1 0.1380 0 1 -1 0.1380 _diffrn_reflns_av_R_equivalents 0.0331 _diffrn_reflns_av_unetI/netI 0.0324 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 13179 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 30.04 _diffrn_reflns_theta_min 2.57 _diffrn_ambient_temperature 120 _diffrn_detector_area_resol_mean 16.15 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.895 _diffrn_measurement_device_type 'Agilent Technologies, Gemini S Ultra kappa-diffractometer' _diffrn_detector_type 'Sapphire3 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'MO K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_current n/a _diffrn_source_voltage n/a _diffrn_standards_number 0 _diffrn_orient_matrix_UB_11 0.0053208000 _diffrn_orient_matrix_UB_12 0.0652486000 _diffrn_orient_matrix_UB_13 0.0394804000 _diffrn_orient_matrix_UB_21 -0.0002099000 _diffrn_orient_matrix_UB_22 -0.0296766000 _diffrn_orient_matrix_UB_23 0.0533112000 _diffrn_orient_matrix_UB_31 0.0891789000 _diffrn_orient_matrix_UB_32 0.0121364000 _diffrn_orient_matrix_UB_33 0.0256847000 _reflns_number_gt 3871 _reflns_number_total 4593 _reflns_threshold_expression I>2\s(I) _computing_cell_refinement 'CrysAlisPro, Agilent Technologies, V1.171.35.10 (2011)' _computing_data_collection 'CrysAlisPro, Agilent Technologies, V1.171.35.10 (2011)' _computing_data_reduction 'CrysAlisPro, Agilent Technologies, V1.171.35.10 (2011)' _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 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.369 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.052 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 248 _refine_ls_number_reflns 4593 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0519 _refine_ls_R_factor_gt 0.0433 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0549P)^2^+0.2793P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1091 _refine_ls_wR_factor_ref 0.1175 _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. Methyl groups were refined as rigid bodies rotating around C---C bonds, with a common refined U for three H atoms. Other H atoms: riding model. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 -0.21993(10) 0.62625(9) 0.05998(9) 0.02266(19) Uani 1 1 d . . . O2 O 0.28329(11) 0.89269(9) 0.01918(9) 0.02170(19) Uani 1 1 d . . . O3 O 0.02725(13) 1.29830(10) 0.42371(11) 0.0373(3) Uani 1 1 d . . . O4 O 0.16388(13) 1.22826(10) 0.59682(10) 0.0326(2) Uani 1 1 d . . . N1 N 0.32403(12) 0.53927(10) 0.24433(10) 0.0167(2) Uani 1 1 d . . . N2 N 0.09641(13) 1.21330(10) 0.47522(11) 0.0233(2) Uani 1 1 d . . . C2 C 0.15395(14) 0.51809(11) 0.21897(11) 0.0162(2) Uani 1 1 d . . . H2 H 0.1048 0.4424 0.2422 0.019 Uiso 1 1 calc R . . C3 C 0.05442(14) 0.59894(11) 0.16321(11) 0.0157(2) Uani 1 1 d . . . C4 C 0.12363(13) 0.72634(11) 0.12949(11) 0.0150(2) Uani 1 1 d . . . H4 H 0.0538 0.7226 0.0341 0.018 Uiso 1 1 calc R . . C5 C 0.30416(14) 0.72960(11) 0.14353(11) 0.0157(2) Uani 1 1 d . . . C6 C 0.39249(14) 0.64217(11) 0.20010(11) 0.0164(2) Uani 1 1 d . . . H6 H 0.5067 0.6517 0.2100 0.020 Uiso 1 1 calc R . . C7 C -0.12855(14) 0.56451(11) 0.12937(11) 0.0171(2) Uani 1 1 d . . . C8 C -0.19979(15) 0.45489(13) 0.18170(12) 0.0218(2) Uani 1 1 d . . . H8A H -0.1561 0.4840 0.2798 0.032(2) Uiso 1 1 d R . . H8B H -0.1667 0.3696 0.1544 0.032(2) Uiso 1 1 d R . . H8C H -0.3229 0.4396 0.1449 0.032(2) Uiso 1 1 d R . . C9 C 0.37580(14) 0.82886(11) 0.08573(11) 0.0167(2) Uani 1 1 d . . . C10 C 0.55939(15) 0.85129(13) 0.10756(14) 0.0242(3) Uani 1 1 d . . . H10A H 0.5800 0.7692 0.0590 0.048(3) Uiso 1 1 d R . . H10B H 0.6284 0.8695 0.2036 0.048(3) Uiso 1 1 d R . . H10C H 0.5891 0.9297 0.0742 0.048(3) Uiso 1 1 d R . . C11 C 0.41590(14) 0.43794(12) 0.28544(11) 0.0168(2) Uani 1 1 d . . . C12 C 0.34430(16) 0.29996(13) 0.22275(12) 0.0242(3) Uani 1 1 d . . . H12 H 0.2336 0.2726 0.1550 0.029 Uiso 1 1 calc R . . C13 C 0.43636(19) 0.20259(14) 0.26025(14) 0.0305(3) Uani 1 1 d . . . H13 H 0.3877 0.1080 0.2191 0.037 Uiso 1 1 calc R . . C14 C 0.59882(18) 0.24290(14) 0.35739(13) 0.0276(3) Uani 1 1 d . . . H14 H 0.6628 0.1762 0.3803 0.033 Uiso 1 1 calc R . . C15 C 0.66835(16) 0.38042(14) 0.42139(12) 0.0233(3) Uani 1 1 d . . . H15 H 0.7790 0.4075 0.4892 0.028 Uiso 1 1 calc R . . C16 C 0.57655(14) 0.47849(13) 0.38651(12) 0.0194(2) Uani 1 1 d . . . H16 H 0.6231 0.5726 0.4313 0.023 Uiso 1 1 calc R . . C17 C 0.11351(14) 0.85577(11) 0.21921(11) 0.0162(2) Uani 1 1 d . . . C18 C 0.21641(16) 0.89260(13) 0.35567(12) 0.0224(3) Uani 1 1 d . . . H18 H 0.2916 0.8370 0.3910 0.027 Uiso 1 1 calc R . . C19 C 0.21054(16) 1.00922(13) 0.44060(12) 0.0229(3) Uani 1 1 d . . . H19 H 0.2800 1.0338 0.5336 0.027 Uiso 1 1 calc R . . C20 C 0.10079(14) 1.08858(11) 0.38586(12) 0.0191(2) Uani 1 1 d . . . C21 C -0.00213(14) 1.05635(12) 0.25099(12) 0.0208(2) Uani 1 1 d . . . H21 H -0.0754 1.1134 0.2159 0.025 Uiso 1 1 calc R . . C22 C 0.00442(14) 0.93824(12) 0.16814(12) 0.0188(2) Uani 1 1 d . . . H22 H -0.0665 0.9135 0.0754 0.023 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 O1 0.0187(4) 0.0214(4) 0.0282(4) 0.0077(3) 0.0080(3) 0.0066(3) O2 0.0229(4) 0.0189(4) 0.0273(4) 0.0129(3) 0.0101(3) 0.0072(3) O3 0.0353(5) 0.0223(5) 0.0442(6) 0.0001(4) 0.0042(5) 0.0163(4) O4 0.0431(6) 0.0236(5) 0.0282(5) -0.0006(4) 0.0143(4) 0.0066(4) N1 0.0177(5) 0.0143(4) 0.0212(5) 0.0085(4) 0.0084(4) 0.0058(4) N2 0.0199(5) 0.0150(5) 0.0321(6) 0.0011(4) 0.0094(4) 0.0033(4) C2 0.0184(5) 0.0133(5) 0.0182(5) 0.0050(4) 0.0084(4) 0.0028(4) C3 0.0174(5) 0.0136(5) 0.0170(5) 0.0040(4) 0.0079(4) 0.0028(4) C4 0.0158(5) 0.0130(5) 0.0173(5) 0.0058(4) 0.0063(4) 0.0044(4) C5 0.0176(5) 0.0128(5) 0.0176(5) 0.0044(4) 0.0078(4) 0.0034(4) C6 0.0173(5) 0.0139(5) 0.0192(5) 0.0052(4) 0.0080(4) 0.0035(4) C7 0.0191(5) 0.0142(5) 0.0181(5) 0.0015(4) 0.0084(4) 0.0038(4) C8 0.0208(6) 0.0213(6) 0.0254(6) 0.0063(5) 0.0123(5) 0.0020(4) C9 0.0199(5) 0.0125(5) 0.0190(5) 0.0042(4) 0.0089(4) 0.0037(4) C10 0.0212(6) 0.0223(6) 0.0359(7) 0.0159(5) 0.0141(5) 0.0066(5) C11 0.0207(5) 0.0174(5) 0.0182(5) 0.0097(4) 0.0104(4) 0.0084(4) C12 0.0277(6) 0.0181(6) 0.0237(6) 0.0061(5) 0.0055(5) 0.0061(5) C13 0.0437(8) 0.0167(6) 0.0313(7) 0.0085(5) 0.0117(6) 0.0122(5) C14 0.0371(7) 0.0288(7) 0.0288(6) 0.0172(5) 0.0167(6) 0.0211(6) C15 0.0219(6) 0.0325(7) 0.0225(6) 0.0142(5) 0.0107(5) 0.0125(5) C16 0.0197(5) 0.0209(6) 0.0219(5) 0.0090(4) 0.0110(4) 0.0061(4) C17 0.0165(5) 0.0132(5) 0.0212(5) 0.0066(4) 0.0089(4) 0.0035(4) C18 0.0281(6) 0.0194(6) 0.0216(6) 0.0083(5) 0.0078(5) 0.0124(5) C19 0.0283(6) 0.0200(6) 0.0194(5) 0.0051(5) 0.0069(5) 0.0092(5) C20 0.0189(5) 0.0127(5) 0.0264(6) 0.0033(4) 0.0106(4) 0.0039(4) C21 0.0173(5) 0.0154(5) 0.0286(6) 0.0062(5) 0.0062(5) 0.0064(4) C22 0.0163(5) 0.0159(5) 0.0219(5) 0.0050(4) 0.0044(4) 0.0045(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.2229(14) . ? O2 C9 1.2283(14) . ? O3 N2 1.2310(14) . ? O4 N2 1.2266(14) . ? N1 C2 1.3836(14) . ? N1 C6 1.3844(14) . ? N1 C11 1.4320(14) . ? N2 C20 1.4703(15) . ? C2 H2 0.9500 . ? C2 C3 1.3453(15) . ? C3 C4 1.5196(15) . ? C3 C7 1.4755(15) . ? C4 H4 1.0000 . ? C4 C5 1.5190(15) . ? C4 C17 1.5278(15) . ? C5 C6 1.3508(15) . ? C5 C9 1.4717(15) . ? C6 H6 0.9500 . ? C7 C8 1.5058(16) . ? C8 H8A 0.9800 . ? C8 H8B 0.9801 . ? C8 H8C 0.9800 . ? C9 C10 1.5074(16) . ? C10 H10A 0.9801 . ? C10 H10B 0.9799 . ? C10 H10C 0.9801 . ? C11 C12 1.3912(17) . ? C11 C16 1.3901(16) . ? C12 H12 0.9500 . ? C12 C13 1.3892(17) . ? C13 H13 0.9500 . ? C13 C14 1.385(2) . ? C14 H14 0.9500 . ? C14 C15 1.387(2) . ? C15 H15 0.9500 . ? C15 C16 1.3876(16) . ? C16 H16 0.9500 . ? C17 C18 1.3952(16) . ? C17 C22 1.3918(15) . ? C18 H18 0.9500 . ? C18 C19 1.3886(17) . ? C19 H19 0.9500 . ? C19 C20 1.3827(16) . ? C20 C21 1.3829(17) . ? C21 H21 0.9500 . ? C21 C22 1.3903(16) . ? C22 H22 0.9500 . ? 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 N1 C6 118.23(9) . . ? C2 N1 C11 120.02(9) . . ? C6 N1 C11 120.09(9) . . ? O3 N2 C20 118.05(11) . . ? O4 N2 O3 123.48(11) . . ? O4 N2 C20 118.46(10) . . ? N1 C2 H2 118.3 . . ? C3 C2 N1 123.49(10) . . ? C3 C2 H2 118.3 . . ? C2 C3 C4 121.94(10) . . ? C2 C3 C7 120.68(10) . . ? C7 C3 C4 117.37(9) . . ? C3 C4 H4 108.4 . . ? C3 C4 C17 110.85(9) . . ? C5 C4 C3 110.06(9) . . ? C5 C4 H4 108.4 . . ? C5 C4 C17 110.59(9) . . ? C17 C4 H4 108.4 . . ? C6 C5 C4 122.24(10) . . ? C6 C5 C9 121.32(10) . . ? C9 C5 C4 116.37(9) . . ? N1 C6 H6 118.5 . . ? C5 C6 N1 122.91(10) . . ? C5 C6 H6 118.5 . . ? O1 C7 C3 119.42(10) . . ? O1 C7 C8 120.99(10) . . ? C3 C7 C8 119.59(10) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C9 C5 118.83(10) . . ? O2 C9 C10 120.68(10) . . ? C5 C9 C10 120.50(10) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 N1 119.68(10) . . ? C16 C11 N1 119.68(10) . . ? C16 C11 C12 120.64(11) . . ? C11 C12 H12 120.3 . . ? C13 C12 C11 119.32(11) . . ? C13 C12 H12 120.3 . . ? C12 C13 H13 119.9 . . ? C14 C13 C12 120.21(12) . . ? C14 C13 H13 119.9 . . ? C13 C14 H14 119.9 . . ? C13 C14 C15 120.18(12) . . ? C15 C14 H14 119.9 . . ? C14 C15 H15 119.9 . . ? C14 C15 C16 120.13(11) . . ? C16 C15 H15 119.9 . . ? C11 C16 H16 120.3 . . ? C15 C16 C11 119.45(11) . . ? C15 C16 H16 120.3 . . ? C18 C17 C4 119.28(10) . . ? C22 C17 C4 121.62(10) . . ? C22 C17 C18 119.10(10) . . ? C17 C18 H18 119.5 . . ? C19 C18 C17 121.02(11) . . ? C19 C18 H18 119.5 . . ? C18 C19 H19 121.0 . . ? C20 C19 C18 118.09(11) . . ? C20 C19 H19 121.0 . . ? C19 C20 N2 118.17(11) . . ? C19 C20 C21 122.68(11) . . ? C21 C20 N2 119.14(10) . . ? C20 C21 H21 120.9 . . ? C20 C21 C22 118.23(10) . . ? C22 C21 H21 120.9 . . ? C17 C22 H22 119.6 . . ? C21 C22 C17 120.88(11) . . ? C21 C22 H22 119.6 . . ? #===END data_4g _database_code_depnum_ccdc_archive 'CCDC 869485' #TrackingRef '- PRG.cif' _audit_creation_date 2012-01-12 _audit_creation_method ; Olex2 1.1-beta (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; 1,1'-(1-Allyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-diyl)diethanone ; _chemical_formula_moiety 'C18 H18 N2 O4' _chemical_formula_sum 'C18 H18 N2 O4' _chemical_formula_weight 326.34 _chemical_melting_point 379.7(5) 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 triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 8.0656(3) _cell_length_b 8.3174(3) _cell_length_c 12.3033(4) _cell_angle_alpha 95.465(2) _cell_angle_beta 99.984(2) _cell_angle_gamma 93.148(2) _cell_volume 807.02(5) _cell_formula_units_Z 2 _cell_measurement_reflns_used 4742 _cell_measurement_temperature 120 _cell_measurement_theta_max 30.90 _cell_measurement_theta_min 2.49 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_T_max 0.8622 _exptl_absorpt_correction_T_min 0.6693 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2006/1 (Bruker,2006) was used for absorption correction. R(int) was 0.0375 before and 0.0259 after correction. The Ratio of minimum to maximum transmission is 0.7763. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'clear light yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 344 _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.07 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of \w scans each set at different \f and/or 2\q angles and each scan (5 s exposure) covering -0.3\% in \w. The crystal to detector distance was 4.83 cm. ; _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_unetI/netI 0.0310 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 13943 _diffrn_reflns_theta_full 29.50 _diffrn_reflns_theta_max 29.50 _diffrn_reflns_theta_min 1.69 _diffrn_ambient_temperature 120 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'sealed X-ray tube' _diffrn_source_current 35.0 _diffrn_source_power 1.75 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _reflns_number_gt 3510 _reflns_number_total 4499 _reflns_threshold_expression I>2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _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 ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.420 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.051 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 289 _refine_ls_number_reflns 4499 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0475 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.3P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1204 _refine_ls_wR_factor_ref 0.1349 _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. ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.06037(12) -0.09224(11) 0.60772(8) 0.0265(2) Uani 1 1 d . . . O2 O -0.34875(11) 0.34815(11) 0.58650(8) 0.0290(2) Uani 1 1 d . . . O3 O -0.34588(17) -0.07884(18) 1.05590(11) 0.0524(3) Uani 1 1 d . . . O4 O -0.20248(19) 0.13255(17) 1.14893(10) 0.0543(4) Uani 1 1 d . . . N1 N 0.23821(13) 0.46256(12) 0.70538(9) 0.0240(2) Uani 1 1 d . . . N2 N -0.25259(17) 0.04435(17) 1.06261(11) 0.0376(3) Uani 1 1 d . . . C1 C 0.26659(15) 0.30036(15) 0.68803(10) 0.0225(2) Uani 1 1 d . . . C2 C 0.14081(15) 0.18298(14) 0.66142(10) 0.0208(2) Uani 1 1 d . . . C3 C -0.04059(15) 0.22093(14) 0.66360(10) 0.0202(2) Uani 1 1 d . . . C4 C -0.05775(15) 0.39859(14) 0.64850(10) 0.0213(2) Uani 1 1 d . . . C5 C 0.07707(15) 0.50782(15) 0.67385(10) 0.0224(2) Uani 1 1 d . . . C6 C 0.38431(16) 0.58186(16) 0.73179(12) 0.0258(3) Uani 1 1 d . . . C7 C 0.47412(18) 0.58427(17) 0.84924(12) 0.0309(3) Uani 1 1 d . . . C8 C 0.6297(2) 0.5431(2) 0.87704(15) 0.0452(4) Uani 1 1 d . . . C9 C 0.17468(16) 0.01544(14) 0.62757(10) 0.0219(2) Uani 1 1 d . . . C10 C 0.35272(18) -0.02092(17) 0.61621(13) 0.0291(3) Uani 1 1 d . . . C11 C -0.22645(15) 0.44849(15) 0.60599(10) 0.0225(2) Uani 1 1 d . . . C12 C -0.24958(17) 0.62349(17) 0.58777(13) 0.0282(3) Uani 1 1 d . . . C13 C -0.09562(15) 0.17548(14) 0.76986(10) 0.0213(2) Uani 1 1 d . . . C14 C -0.21383(17) 0.04621(17) 0.76554(11) 0.0277(3) Uani 1 1 d . . . C15 C -0.26585(18) 0.00199(18) 0.86122(12) 0.0321(3) Uani 1 1 d . . . C16 C -0.19724(17) 0.09045(17) 0.96100(11) 0.0285(3) Uani 1 1 d . . . C17 C -0.0785(2) 0.21852(18) 0.96926(12) 0.0323(3) Uani 1 1 d . . . C18 C -0.02788(19) 0.26044(17) 0.87248(11) 0.0301(3) Uani 1 1 d . . . H1 H 0.383(2) 0.2811(19) 0.6930(13) 0.025(4) Uiso 1 1 d . . . H3 H -0.116(2) 0.1524(19) 0.6007(13) 0.024(4) Uiso 1 1 d . . . H5 H 0.0699(19) 0.6216(19) 0.6699(13) 0.024(4) Uiso 1 1 d . . . H6A H 0.339(2) 0.686(2) 0.7181(15) 0.035(4) Uiso 1 1 d . . . H6B H 0.462(2) 0.552(2) 0.6779(15) 0.036(4) Uiso 1 1 d . . . H7 H 0.410(2) 0.622(2) 0.9051(16) 0.038(5) Uiso 1 1 d . . . H8A H 0.682(3) 0.551(2) 0.9556(17) 0.048(5) Uiso 1 1 d . . . H8B H 0.697(3) 0.504(3) 0.821(2) 0.061(6) Uiso 1 1 d . . . H10A H 0.351(2) -0.131(2) 0.5765(15) 0.037(5) Uiso 1 1 d . . . H10B H 0.422(3) -0.015(2) 0.6886(18) 0.048(5) Uiso 1 1 d . . . H10C H 0.401(2) 0.058(2) 0.5751(16) 0.043(5) Uiso 1 1 d . . . H12A H -0.233(2) 0.691(2) 0.6585(18) 0.048(5) Uiso 1 1 d . . . H12B H -0.365(2) 0.633(2) 0.5473(15) 0.034(4) Uiso 1 1 d . . . H12C H -0.164(2) 0.667(2) 0.5471(16) 0.045(5) Uiso 1 1 d . . . H14 H -0.259(2) -0.015(2) 0.6927(14) 0.030(4) Uiso 1 1 d . . . H15 H -0.351(2) -0.088(2) 0.8563(16) 0.040(5) Uiso 1 1 d . . . H17 H -0.033(2) 0.279(2) 1.0396(16) 0.040(5) Uiso 1 1 d . . . H18 H 0.059(2) 0.351(2) 0.8772(15) 0.039(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0293(5) 0.0219(4) 0.0278(5) 0.0022(3) 0.0051(4) -0.0005(3) O2 0.0213(4) 0.0278(5) 0.0368(5) 0.0037(4) 0.0026(4) 0.0003(4) O3 0.0498(7) 0.0687(9) 0.0480(7) 0.0282(6) 0.0224(6) 0.0033(6) O4 0.0831(10) 0.0586(8) 0.0289(6) 0.0109(5) 0.0224(6) 0.0244(7) N1 0.0192(5) 0.0206(5) 0.0313(5) 0.0023(4) 0.0031(4) -0.0008(4) N2 0.0425(7) 0.0485(8) 0.0299(6) 0.0169(6) 0.0161(5) 0.0226(6) C1 0.0201(6) 0.0226(6) 0.0252(6) 0.0036(4) 0.0043(4) 0.0031(4) C2 0.0215(5) 0.0215(5) 0.0201(5) 0.0038(4) 0.0044(4) 0.0031(4) C3 0.0193(5) 0.0200(5) 0.0213(5) 0.0026(4) 0.0036(4) 0.0002(4) C4 0.0208(5) 0.0216(5) 0.0222(5) 0.0039(4) 0.0046(4) 0.0023(4) C5 0.0209(6) 0.0214(5) 0.0255(6) 0.0041(4) 0.0050(4) 0.0025(4) C6 0.0216(6) 0.0230(6) 0.0323(7) 0.0040(5) 0.0039(5) -0.0028(5) C7 0.0306(7) 0.0287(6) 0.0321(7) 0.0024(5) 0.0051(5) -0.0049(5) C8 0.0341(8) 0.0622(11) 0.0383(9) 0.0142(8) 0.0001(7) 0.0000(7) C9 0.0261(6) 0.0217(5) 0.0188(5) 0.0040(4) 0.0049(4) 0.0026(4) C10 0.0283(7) 0.0252(6) 0.0359(7) 0.0038(5) 0.0105(6) 0.0054(5) C11 0.0217(6) 0.0255(6) 0.0213(5) 0.0039(4) 0.0054(4) 0.0030(4) C12 0.0234(6) 0.0273(6) 0.0358(7) 0.0109(5) 0.0053(5) 0.0038(5) C13 0.0204(5) 0.0222(5) 0.0224(5) 0.0043(4) 0.0049(4) 0.0046(4) C14 0.0270(6) 0.0300(6) 0.0259(6) 0.0026(5) 0.0063(5) -0.0033(5) C15 0.0298(7) 0.0360(7) 0.0330(7) 0.0091(6) 0.0107(5) -0.0014(6) C16 0.0296(6) 0.0351(7) 0.0260(6) 0.0111(5) 0.0115(5) 0.0136(5) C17 0.0407(8) 0.0335(7) 0.0221(6) 0.0017(5) 0.0038(5) 0.0058(6) C18 0.0344(7) 0.0293(6) 0.0250(6) 0.0026(5) 0.0029(5) -0.0035(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 O1 C9 1.2253(15) . ? O2 C11 1.2314(15) . ? O3 N2 1.2250(19) . ? O4 N2 1.2246(19) . ? N1 C1 1.3835(16) . ? N1 C5 1.3741(16) . ? N1 C6 1.4684(16) . ? N2 C16 1.4748(17) . ? C1 C2 1.3434(17) . ? C1 H1 0.951(16) . ? C2 C3 1.5178(16) . ? C2 C9 1.4699(17) . ? C3 C4 1.5176(16) . ? C3 C13 1.5251(16) . ? C3 H3 1.003(16) . ? C4 C5 1.3509(17) . ? C4 C11 1.4676(17) . ? C5 H5 0.957(16) . ? C6 C7 1.498(2) . ? C6 H6A 0.978(18) . ? C6 H6B 1.012(18) . ? C7 C8 1.315(2) . ? C7 H7 0.967(19) . ? C8 H8A 0.98(2) . ? C8 H8B 1.00(2) . ? C9 C10 1.5107(18) . ? C10 H10A 0.996(18) . ? C10 H10B 0.96(2) . ? C10 H10C 0.97(2) . ? C11 C12 1.5103(18) . ? C12 H12A 0.97(2) . ? C12 H12B 0.985(18) . ? C12 H12C 0.99(2) . ? C13 C14 1.3881(17) . ? C13 C18 1.3930(18) . ? C14 C15 1.3906(19) . ? C14 H14 0.988(17) . ? C15 C16 1.379(2) . ? C15 H15 0.980(19) . ? C16 C17 1.377(2) . ? C17 C18 1.392(2) . ? C17 H17 0.961(19) . ? C18 H18 0.988(18) . ? 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 C6 118.55(10) . . ? C5 N1 C1 118.20(10) . . ? C5 N1 C6 121.70(10) . . ? O3 N2 C16 118.44(13) . . ? O4 N2 O3 123.90(13) . . ? O4 N2 C16 117.66(14) . . ? N1 C1 H1 113.5(9) . . ? C2 C1 N1 122.75(11) . . ? C2 C1 H1 123.6(9) . . ? C1 C2 C3 120.69(11) . . ? C1 C2 C9 120.99(11) . . ? C9 C2 C3 118.32(10) . . ? C2 C3 C13 111.22(9) . . ? C2 C3 H3 108.4(9) . . ? C4 C3 C2 108.75(9) . . ? C4 C3 C13 112.36(10) . . ? C4 C3 H3 109.6(9) . . ? C13 C3 H3 106.4(9) . . ? C5 C4 C3 121.38(11) . . ? C5 C4 C11 120.88(11) . . ? C11 C4 C3 117.75(10) . . ? N1 C5 H5 114.3(9) . . ? C4 C5 N1 122.02(11) . . ? C4 C5 H5 123.7(9) . . ? N1 C6 C7 112.14(11) . . ? N1 C6 H6A 105.3(10) . . ? N1 C6 H6B 106.7(10) . . ? C7 C6 H6A 111.3(10) . . ? C7 C6 H6B 110.8(10) . . ? H6A C6 H6B 110.2(14) . . ? C6 C7 H7 115.1(11) . . ? C8 C7 C6 123.87(15) . . ? C8 C7 H7 121.0(11) . . ? C7 C8 H8A 119.7(12) . . ? C7 C8 H8B 122.2(13) . . ? H8A C8 H8B 118.1(18) . . ? O1 C9 C2 120.63(11) . . ? O1 C9 C10 120.67(11) . . ? C2 C9 C10 118.69(11) . . ? C9 C10 H10A 108.9(10) . . ? C9 C10 H10B 109.5(12) . . ? C9 C10 H10C 110.4(11) . . ? H10A C10 H10B 110.3(16) . . ? H10A C10 H10C 109.8(15) . . ? H10B C10 H10C 107.8(16) . . ? O2 C11 C4 119.98(11) . . ? O2 C11 C12 120.27(11) . . ? C4 C11 C12 119.74(11) . . ? C11 C12 H12A 110.6(12) . . ? C11 C12 H12B 109.5(10) . . ? C11 C12 H12C 111.4(11) . . ? H12A C12 H12B 108.8(15) . . ? H12A C12 H12C 105.8(16) . . ? H12B C12 H12C 110.7(15) . . ? C14 C13 C3 119.99(11) . . ? C14 C13 C18 118.82(12) . . ? C18 C13 C3 121.19(11) . . ? C13 C14 C15 121.14(13) . . ? C13 C14 H14 118.3(10) . . ? C15 C14 H14 120.5(10) . . ? C14 C15 H15 119.9(11) . . ? C16 C15 C14 118.23(13) . . ? C16 C15 H15 121.8(11) . . ? C15 C16 N2 118.40(13) . . ? C17 C16 N2 119.03(13) . . ? C17 C16 C15 122.56(12) . . ? C16 C17 C18 118.25(13) . . ? C16 C17 H17 121.2(11) . . ? C18 C17 H17 120.6(11) . . ? C13 C18 H18 119.8(11) . . ? C17 C18 C13 120.99(13) . . ? C17 C18 H18 119.2(11) . . ? #===END data_4h _database_code_depnum_ccdc_archive 'CCDC 869486' #TrackingRef '- PRG.cif' _audit_creation_date 2011-03-23 _audit_creation_method ; Olex2 1.1-beta (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; 1,1'-(1-Allyl-4-phenyl-1,4-dihydropyridine-3,5-diyl)diethanone ; _chemical_formula_moiety 'C18 H19 N O2' _chemical_formula_sum 'C18 H19 N O2' _chemical_formula_weight 281.34 _chemical_melting_point 391.7(5) 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 monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'I 2/a' _space_group_name_Hall '-I 2ya' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y, -z' 3 'x+1/2, y+1/2, z+1/2' 4 '-x+1, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x-1/2, -y, z' 7 '-x+1/2, -y+1/2, -z+1/2' 8 'x, -y+1/2, z+1/2' _cell_length_a 16.2061(7) _cell_length_b 10.9226(4) _cell_length_c 17.1311(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.915(10) _cell_angle_gamma 90.00 _cell_volume 3025.3(2) _cell_formula_units_Z 8 _cell_measurement_reflns_used 5226 _cell_measurement_temperature 120 _cell_measurement_theta_max 29.91 _cell_measurement_theta_min 2.21 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_crystal_colour 'light yellow' _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1200 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.16 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 3 sets of \w scans each set at different \f angles and each scan (10 s exposure) covering -0.3\% in \w. The crystal to detector distance was 4.84 cm. ; loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 1.00 1.00 0.0800 0.00 -1.00 -1.00 0.0800 0.00 1.00 -1.00 0.0800 0.00 -1.00 1.00 0.0800 1.00 0.00 0.00 0.1100 -1.00 0.00 0.00 0.1100 _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_av_unetI/netI 0.0290 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 16936 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.21 _diffrn_ambient_temperature 120 _diffrn_detector_area_resol_mean 5.6 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker SMART 6000 CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_current 35.0 _diffrn_source_power 1.75 _diffrn_source_target MO _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _reflns_number_gt 2699 _reflns_number_total 3486 _reflns_threshold_expression I>2\s(I) _computing_cell_refinement 'SAINT v7.46A (Bruker, 2008)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v7.46A (Bruker, 2008)' _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 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2008)/Bruker' _refine_diff_density_max 0.289 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.043 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 266 _refine_ls_number_reflns 3486 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0545 _refine_ls_R_factor_gt 0.0403 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0580P)^2^+1.2413P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1036 _refine_ls_wR_factor_ref 0.1123 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.63940(6) 0.70604(9) 0.31942(6) 0.0316(2) Uani 1 1 d . . . O2 O 0.35346(6) 0.72153(9) 0.18725(6) 0.0339(3) Uani 1 1 d . . . N N 0.44876(7) 0.38276(9) 0.33858(6) 0.0236(2) Uani 1 1 d . . . C1 C 0.43439(9) 0.26010(12) 0.36990(8) 0.0248(3) Uani 1 1 d . . . H1A H 0.3904(9) 0.2209(14) 0.3360(9) 0.027(4) Uiso 1 1 d . . . H1B H 0.4876(9) 0.2145(14) 0.3688(8) 0.027(4) Uiso 1 1 d . . . C2 C 0.52400(8) 0.43848(12) 0.35535(7) 0.0226(3) Uani 1 1 d . . . H2 H 0.5654(9) 0.3832(13) 0.3772(8) 0.026(4) Uiso 1 1 d . . . C3 C 0.53894(7) 0.55549(12) 0.33621(7) 0.0209(3) Uani 1 1 d . . . C4 C 0.46896(7) 0.63762(11) 0.30373(7) 0.0199(3) Uani 1 1 d . . . H4 H 0.4898(8) 0.6918(12) 0.2633(8) 0.015(3) Uiso 1 1 d . . . C5 C 0.39877(7) 0.55934(12) 0.26819(7) 0.0212(3) Uani 1 1 d . . . C6 C 0.39015(8) 0.44172(12) 0.29046(7) 0.0225(3) Uani 1 1 d . . . H6 H 0.3449(9) 0.3912(13) 0.2720(8) 0.023(4) Uiso 1 1 d . . . C7 C 0.62319(8) 0.60486(12) 0.34561(7) 0.0237(3) Uani 1 1 d . . . C8 C 0.69070(9) 0.53063(14) 0.38891(9) 0.0293(3) Uani 1 1 d . . . H8A H 0.7422(10) 0.5808(15) 0.3916(9) 0.038(4) Uiso 1 1 d . . . H8B H 0.6745(10) 0.5146(15) 0.4437(10) 0.041(5) Uiso 1 1 d . . . H8C H 0.6988(11) 0.4526(17) 0.3646(11) 0.047(5) Uiso 1 1 d . . . C9 C 0.34018(8) 0.61725(13) 0.21029(7) 0.0261(3) Uani 1 1 d . . . C10 C 0.26355(11) 0.55049(18) 0.17915(11) 0.0412(4) Uani 1 1 d . . . H10A H 0.2396(13) 0.5909(19) 0.1356(13) 0.063(6) Uiso 1 1 d . . . H10B H 0.2265(17) 0.538(2) 0.2179(17) 0.099(9) Uiso 1 1 d . . . H10C H 0.2761(15) 0.468(3) 0.1628(15) 0.091(8) Uiso 1 1 d . . . C11 C 0.43989(7) 0.72259(11) 0.36708(7) 0.0198(3) Uani 1 1 d . . . C12 C 0.46408(8) 0.84491(12) 0.36923(8) 0.0237(3) Uani 1 1 d . . . H12 H 0.4982(9) 0.8755(14) 0.3272(9) 0.031(4) Uiso 1 1 d . . . C13 C 0.44019(8) 0.92196(12) 0.42789(8) 0.0273(3) Uani 1 1 d . . . H13 H 0.4568(10) 1.0075(15) 0.4282(9) 0.035(4) Uiso 1 1 d . . . C14 C 0.39159(8) 0.87849(13) 0.48534(8) 0.0268(3) Uani 1 1 d . . . H14 H 0.3755(10) 0.9322(15) 0.5272(10) 0.037(4) Uiso 1 1 d . . . C15 C 0.36630(8) 0.75710(13) 0.48365(8) 0.0254(3) Uani 1 1 d . . . H15 H 0.3320(9) 0.7241(14) 0.5249(9) 0.028(4) Uiso 1 1 d . . . C16 C 0.39037(8) 0.67973(12) 0.42476(7) 0.0227(3) Uani 1 1 d . . . H16 H 0.3744(9) 0.5965(15) 0.4239(8) 0.026(4) Uiso 1 1 d . . . C17 C 0.41079(8) 0.26446(12) 0.45314(8) 0.0245(3) Uani 1 1 d . . . H17 H 0.4470(10) 0.3105(14) 0.4894(9) 0.031(4) Uiso 1 1 d . . . C18 C 0.34755(9) 0.20581(14) 0.47865(9) 0.0334(3) Uani 1 1 d . . . H18A H 0.3099(11) 0.1572(16) 0.4418(10) 0.044(5) Uiso 1 1 d . . . H18B H 0.3351(11) 0.2048(16) 0.5352(11) 0.048(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0294(5) 0.0311(5) 0.0339(5) 0.0083(4) -0.0003(4) -0.0048(4) O2 0.0341(6) 0.0328(6) 0.0338(5) 0.0115(4) -0.0060(4) -0.0036(4) N 0.0278(6) 0.0189(5) 0.0238(5) 0.0003(4) 0.0003(4) -0.0015(4) C1 0.0313(7) 0.0184(6) 0.0247(6) 0.0007(5) 0.0017(5) -0.0007(5) C2 0.0242(6) 0.0231(6) 0.0204(6) -0.0004(5) 0.0012(5) 0.0028(5) C3 0.0227(6) 0.0227(6) 0.0173(6) -0.0014(5) 0.0010(5) 0.0016(5) C4 0.0222(6) 0.0197(6) 0.0177(6) 0.0015(5) 0.0011(5) -0.0013(5) C5 0.0228(6) 0.0228(6) 0.0179(6) -0.0018(5) 0.0005(5) -0.0003(5) C6 0.0244(6) 0.0237(6) 0.0194(6) -0.0034(5) 0.0019(5) -0.0023(5) C7 0.0230(6) 0.0270(7) 0.0211(6) -0.0005(5) 0.0023(5) 0.0013(5) C8 0.0230(7) 0.0307(8) 0.0341(8) 0.0020(6) 0.0005(6) 0.0011(6) C9 0.0275(7) 0.0307(7) 0.0196(6) 0.0015(5) -0.0005(5) -0.0025(5) C10 0.0395(9) 0.0460(10) 0.0356(9) 0.0102(8) -0.0158(7) -0.0117(8) C11 0.0177(6) 0.0223(6) 0.0187(6) 0.0001(5) -0.0033(4) 0.0015(5) C12 0.0231(6) 0.0232(6) 0.0243(6) 0.0013(5) -0.0013(5) -0.0002(5) C13 0.0290(7) 0.0209(7) 0.0313(7) -0.0026(5) -0.0039(5) 0.0010(5) C14 0.0277(7) 0.0279(7) 0.0242(6) -0.0058(5) -0.0024(5) 0.0064(5) C15 0.0234(6) 0.0306(7) 0.0222(6) 0.0014(5) 0.0015(5) 0.0032(5) C16 0.0231(6) 0.0219(6) 0.0228(6) 0.0010(5) -0.0008(5) -0.0008(5) C17 0.0258(7) 0.0232(6) 0.0240(6) -0.0010(5) -0.0015(5) 0.0015(5) C18 0.0320(8) 0.0351(8) 0.0339(8) -0.0055(6) 0.0081(6) -0.0019(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 C7 1.2280(16) . ? O2 C9 1.2292(16) . ? N C1 1.4677(16) . ? N C2 1.3754(17) . ? N C6 1.3746(16) . ? C1 H1A 0.985(15) . ? C1 H1B 0.996(15) . ? C1 C17 1.5022(18) . ? C2 H2 0.960(15) . ? C2 C3 1.3455(18) . ? C3 C4 1.5213(17) . ? C3 C7 1.4665(18) . ? C4 H4 0.987(13) . ? C4 C5 1.5169(17) . ? C4 C11 1.5268(17) . ? C5 C6 1.3501(18) . ? C5 C9 1.4687(17) . ? C6 H6 0.955(15) . ? C7 C8 1.5145(18) . ? C8 H8A 0.997(17) . ? C8 H8B 1.007(18) . ? C8 H8C 0.961(19) . ? C9 C10 1.506(2) . ? C10 H10A 0.93(2) . ? C10 H10B 0.94(3) . ? C10 H10C 0.97(3) . ? C11 C12 1.3922(18) . ? C11 C16 1.3956(17) . ? C12 H12 0.995(16) . ? C12 C13 1.3861(19) . ? C13 H13 0.972(16) . ? C13 C14 1.386(2) . ? C14 H14 0.975(17) . ? C14 C15 1.3875(19) . ? C15 H15 0.996(15) . ? C15 C16 1.3920(18) . ? C16 H16 0.945(16) . ? C17 H17 0.966(16) . ? C17 C18 1.309(2) . ? C18 H18A 1.000(18) . ? C18 H18B 1.003(18) . ? 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 N C1 119.22(11) . . ? C6 N C1 121.77(11) . . ? C6 N C2 118.97(11) . . ? N C1 H1A 107.9(9) . . ? N C1 H1B 106.9(9) . . ? N C1 C17 112.03(11) . . ? H1A C1 H1B 111.3(12) . . ? C17 C1 H1A 110.6(9) . . ? C17 C1 H1B 108.0(8) . . ? N C2 H2 112.9(9) . . ? C3 C2 N 122.76(12) . . ? C3 C2 H2 124.1(9) . . ? C2 C3 C4 120.47(11) . . ? C2 C3 C7 120.28(11) . . ? C7 C3 C4 119.25(11) . . ? C3 C4 H4 109.2(7) . . ? C3 C4 C11 110.91(10) . . ? C5 C4 C3 109.53(10) . . ? C5 C4 H4 109.9(7) . . ? C5 C4 C11 111.62(10) . . ? C11 C4 H4 105.7(8) . . ? C6 C5 C4 120.81(11) . . ? C6 C5 C9 121.74(12) . . ? C9 C5 C4 117.44(11) . . ? N C6 H6 114.3(9) . . ? C5 C6 N 122.32(12) . . ? C5 C6 H6 123.2(9) . . ? O1 C7 C3 120.76(11) . . ? O1 C7 C8 119.70(12) . . ? C3 C7 C8 119.53(11) . . ? C7 C8 H8A 107.6(9) . . ? C7 C8 H8B 108.9(9) . . ? C7 C8 H8C 112.2(11) . . ? H8A C8 H8B 108.9(13) . . ? H8A C8 H8C 111.6(14) . . ? H8B C8 H8C 107.5(14) . . ? O2 C9 C5 119.78(12) . . ? O2 C9 C10 119.54(12) . . ? C5 C9 C10 120.68(12) . . ? C9 C10 H10A 110.1(13) . . ? C9 C10 H10B 111.9(16) . . ? C9 C10 H10C 111.6(15) . . ? H10A C10 H10B 113(2) . . ? H10A C10 H10C 107.0(19) . . ? H10B C10 H10C 103(2) . . ? C12 C11 C4 120.14(11) . . ? C12 C11 C16 118.53(11) . . ? C16 C11 C4 121.31(11) . . ? C11 C12 H12 118.2(9) . . ? C13 C12 C11 120.65(12) . . ? C13 C12 H12 121.2(9) . . ? C12 C13 H13 119.8(10) . . ? C14 C13 C12 120.49(13) . . ? C14 C13 H13 119.7(10) . . ? C13 C14 H14 120.6(10) . . ? C13 C14 C15 119.60(12) . . ? C15 C14 H14 119.8(10) . . ? C14 C15 H15 120.6(9) . . ? C14 C15 C16 119.88(12) . . ? C16 C15 H15 119.5(9) . . ? C11 C16 H16 118.8(9) . . ? C15 C16 C11 120.84(12) . . ? C15 C16 H16 120.4(9) . . ? C1 C17 H17 116.4(9) . . ? C18 C17 C1 123.87(13) . . ? C18 C17 H17 119.7(9) . . ? C17 C18 H18A 120.5(10) . . ? C17 C18 H18B 122.8(11) . . ? H18A C18 H18B 116.7(14) . . ? #===END data_4i _database_code_depnum_ccdc_archive 'CCDC 869487' #TrackingRef '- PRG.cif' _audit_creation_date 2012-02-03 _audit_creation_method ; Olex2 1.1-beta (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ;1,1'-(1-Allyl-4-(4-methoxyphenyl)-1,4-dihydropyridine-3,5-diyl)diethanone ; _chemical_formula_moiety 'C19 H21 N O3' _chemical_formula_sum 'C19 H21 N O3' _chemical_formula_weight 311.37 _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 0.0033 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 monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 8.5218(6) _cell_length_b 19.4587(16) _cell_length_c 9.7216(7) _cell_angle_alpha 90.00 _cell_angle_beta 97.456(9) _cell_angle_gamma 90.00 _cell_volume 1598.4(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9897 _cell_measurement_temperature 120 _cell_measurement_theta_max 29.996 _cell_measurement_theta_min 2.410 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_T_max 0.7460 _exptl_absorpt_correction_T_min 0.6614 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; ? was used for absorption correction. R(int) was 0.0607 before and 0.0441 after correction. The Ratio of minimum to maximum transmission is 0.8866. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'light yellow' _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 664 _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 5 sets of \w scans each set at different \f and/or 2\q angles and each scan (3 s exposure) covering -0.3\% in \w. The crystal to detector distance was 4.83 cm. ; _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_unetI/netI 0.0148 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 29459 _diffrn_reflns_theta_full 30.00 _diffrn_reflns_theta_max 30.00 _diffrn_reflns_theta_min 2.09 _diffrn_ambient_temperature 120 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'sealed X-ray tube' _diffrn_source_current 30.0 _diffrn_source_power 1.5 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _reflns_number_gt 4033 _reflns_number_total 4652 _reflns_threshold_expression I>2\s(I) _computing_cell_refinement 'SAINT v7.46A (Bruker, 2008)' _computing_data_collection 'SMART v5.630 (Bruker, 2003)' _computing_data_reduction 'SAINT v7.46A (Bruker, 2008)' _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 ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.449 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.049 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 222 _refine_ls_number_reflns 4652 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0458 _refine_ls_R_factor_gt 0.0403 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0702P)^2^+0.3634P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1148 _refine_ls_wR_factor_ref 0.1209 _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. Methyl groups were refined as rigid bodies rotating around C---C or O---C bonds, with a common refined U for three H atoms. Vinyl hydrogens at C(19) - refall. Other H atoms: riding model. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.63228(9) 0.18256(4) 0.38283(9) 0.0337(2) Uani 1 1 d . . . O2 O 0.41909(9) -0.03862(4) 0.15821(8) 0.02665(16) Uani 1 1 d . . . O3 O 0.03782(9) 0.07985(4) 0.67334(7) 0.02503(16) Uani 1 1 d . . . N1 N 0.23868(9) 0.17943(4) -0.00650(8) 0.01978(16) Uani 1 1 d . . . C1 C 0.13652(11) 0.21942(5) -0.10958(10) 0.02272(19) Uani 1 1 d . . . H1A H 0.1190 0.1930 -0.1972 0.027 Uiso 1 1 calc R . . H1B H 0.1917 0.2625 -0.1284 0.027 Uiso 1 1 calc R . . C2 C 0.34024(10) 0.21219(5) 0.09362(9) 0.01919(18) Uani 1 1 d . . . H2 H 0.3499 0.2608 0.0894 0.023 Uiso 1 1 calc R . . C3 C 0.42721(10) 0.17783(4) 0.19825(9) 0.01796(17) Uani 1 1 d . . . C4 C 0.40025(10) 0.10153(4) 0.22153(9) 0.01679(17) Uani 1 1 d . . . H4 H 0.5053 0.0789 0.2477 0.020 Uiso 1 1 calc R . . C5 C 0.32200(10) 0.06987(4) 0.08740(9) 0.01731(17) Uani 1 1 d . . . C6 C 0.24020(10) 0.10862(5) -0.01258(9) 0.01864(17) Uani 1 1 d . . . H6 H 0.1817 0.0863 -0.0898 0.022 Uiso 1 1 calc R . . C7 C 0.54664(11) 0.21432(5) 0.29321(10) 0.02256(19) Uani 1 1 d . . . C8 C 0.56371(13) 0.29148(5) 0.28086(12) 0.0285(2) Uani 1 1 d . . . H8A H 0.5907 0.3029 0.1886 0.050(3) Uiso 1 1 calc R . . H8B H 0.6478 0.3077 0.3517 0.050(3) Uiso 1 1 calc R . . H8C H 0.4637 0.3137 0.2943 0.050(3) Uiso 1 1 calc R . . C9 C 0.33451(11) -0.00497(5) 0.07113(10) 0.01982(18) Uani 1 1 d . . . C10 C 0.24220(13) -0.04077(5) -0.05175(11) 0.0281(2) Uani 1 1 d . . . H10A H 0.2707 -0.0896 -0.0504 0.058(3) Uiso 1 1 calc R . . H10B H 0.2675 -0.0198 -0.1378 0.058(3) Uiso 1 1 calc R . . H10C H 0.1286 -0.0361 -0.0466 0.058(3) Uiso 1 1 calc R . . C11 C 0.30062(10) 0.09155(4) 0.33992(9) 0.01616(16) Uani 1 1 d . . . C12 C 0.37205(11) 0.08302(5) 0.47681(9) 0.01991(18) Uani 1 1 d . . . H12 H 0.4841 0.0804 0.4957 0.024 Uiso 1 1 calc R . . C13 C 0.28165(11) 0.07829(5) 0.58528(9) 0.02179(19) Uani 1 1 d . . . H13 H 0.3320 0.0722 0.6775 0.026 Uiso 1 1 calc R . . C14 C 0.11690(11) 0.08245(5) 0.55922(9) 0.01902(18) Uani 1 1 d . . . C15 C 0.04317(10) 0.08869(5) 0.42361(9) 0.01860(17) Uani 1 1 d . . . H15 H -0.0690 0.0902 0.4046 0.022 Uiso 1 1 calc R . . C16 C 0.13603(10) 0.09277(4) 0.31599(9) 0.01765(17) Uani 1 1 d . . . H16 H 0.0854 0.0965 0.2233 0.021 Uiso 1 1 calc R . . C17 C -0.13092(12) 0.08779(5) 0.64982(11) 0.0263(2) Uani 1 1 d . . . H17A H -0.1726 0.0895 0.7391 0.035(2) Uiso 1 1 calc R . . H17B H -0.1779 0.0488 0.5955 0.035(2) Uiso 1 1 calc R . . H17C H -0.1575 0.1305 0.5988 0.035(2) Uiso 1 1 calc R . . C18 C -0.02071(11) 0.23701(5) -0.06581(10) 0.02370(19) Uani 1 1 d . . . H18 H -0.0927 0.2618 -0.1304 0.028 Uiso 1 1 calc R . . C19 C -0.06879(13) 0.22134(5) 0.05401(11) 0.0269(2) Uani 1 1 d . . . H19A H -0.0016(17) 0.1957(7) 0.1250(15) 0.031(3) Uiso 1 1 d . . . H19B H -0.1729(18) 0.2346(8) 0.0757(15) 0.036(4) 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 0.0289(4) 0.0283(4) 0.0394(4) 0.0082(3) -0.0122(3) -0.0084(3) O2 0.0284(4) 0.0198(3) 0.0315(4) 0.0025(3) 0.0027(3) 0.0034(3) O3 0.0263(4) 0.0319(4) 0.0179(3) -0.0017(3) 0.0068(3) -0.0036(3) N1 0.0212(4) 0.0182(4) 0.0193(4) 0.0024(3) 0.0000(3) 0.0014(3) C1 0.0249(4) 0.0223(4) 0.0203(4) 0.0057(3) 0.0002(3) 0.0022(3) C2 0.0191(4) 0.0171(4) 0.0216(4) 0.0007(3) 0.0039(3) -0.0009(3) C3 0.0166(4) 0.0166(4) 0.0209(4) 0.0003(3) 0.0031(3) -0.0019(3) C4 0.0160(4) 0.0163(4) 0.0181(4) 0.0006(3) 0.0021(3) 0.0000(3) C5 0.0174(4) 0.0169(4) 0.0182(4) -0.0003(3) 0.0045(3) -0.0003(3) C6 0.0200(4) 0.0190(4) 0.0174(4) -0.0009(3) 0.0042(3) -0.0009(3) C7 0.0194(4) 0.0217(4) 0.0261(4) 0.0014(3) 0.0009(3) -0.0043(3) C8 0.0264(5) 0.0214(4) 0.0360(5) 0.0001(4) -0.0026(4) -0.0058(4) C9 0.0203(4) 0.0174(4) 0.0230(4) -0.0010(3) 0.0074(3) -0.0008(3) C10 0.0339(5) 0.0213(4) 0.0287(5) -0.0056(4) 0.0029(4) -0.0029(4) C11 0.0175(4) 0.0137(3) 0.0173(4) -0.0001(3) 0.0022(3) -0.0003(3) C12 0.0179(4) 0.0213(4) 0.0198(4) 0.0001(3) -0.0007(3) -0.0017(3) C13 0.0238(4) 0.0248(4) 0.0159(4) 0.0000(3) -0.0005(3) -0.0031(3) C14 0.0234(4) 0.0172(4) 0.0170(4) -0.0012(3) 0.0045(3) -0.0022(3) C15 0.0179(4) 0.0186(4) 0.0194(4) 0.0003(3) 0.0026(3) -0.0001(3) C16 0.0188(4) 0.0181(4) 0.0157(4) 0.0009(3) 0.0010(3) -0.0001(3) C17 0.0281(5) 0.0241(4) 0.0289(5) 0.0007(4) 0.0126(4) 0.0004(4) C18 0.0226(4) 0.0203(4) 0.0266(5) 0.0026(3) -0.0026(3) 0.0012(3) C19 0.0263(5) 0.0252(5) 0.0291(5) 0.0008(4) 0.0027(4) 0.0032(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.2283(12) . ? O2 C9 1.2274(12) . ? O3 C14 1.3718(11) . ? O3 C17 1.4347(12) . ? N1 C2 1.3727(12) . ? N1 C6 1.3794(12) . ? N1 C1 1.4632(11) . ? C1 C18 1.4972(14) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.3547(12) . ? C2 H2 0.9500 . ? C3 C7 1.4658(12) . ? C3 C4 1.5236(12) . ? C4 C5 1.5163(12) . ? C4 C11 1.5287(12) . ? C4 H4 1.0000 . ? C5 C6 1.3502(12) . ? C5 C9 1.4703(12) . ? C6 H6 0.9500 . ? C7 C8 1.5147(14) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.5123(14) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C16 1.3919(12) . ? C11 C12 1.3996(12) . ? C12 C13 1.3874(13) . ? C12 H12 0.9500 . ? C13 C14 1.3963(13) . ? C13 H13 0.9500 . ? C14 C15 1.3902(12) . ? C15 C16 1.3935(12) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.3196(15) . ? C18 H18 0.9500 . ? C19 H19A 0.975(14) . ? C19 H19B 0.973(15) . ? 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 O3 C17 117.04(8) . . ? C2 N1 C6 119.06(8) . . ? C2 N1 C1 120.20(8) . . ? C6 N1 C1 120.66(8) . . ? N1 C1 C18 113.69(8) . . ? N1 C1 H1A 108.8 . . ? C18 C1 H1A 108.8 . . ? N1 C1 H1B 108.8 . . ? C18 C1 H1B 108.8 . . ? H1A C1 H1B 107.7 . . ? C3 C2 N1 122.44(8) . . ? C3 C2 H2 118.8 . . ? N1 C2 H2 118.8 . . ? C2 C3 C7 120.08(8) . . ? C2 C3 C4 120.94(8) . . ? C7 C3 C4 118.96(8) . . ? C5 C4 C3 109.03(7) . . ? C5 C4 C11 111.75(7) . . ? C3 C4 C11 110.17(7) . . ? C5 C4 H4 108.6 . . ? C3 C4 H4 108.6 . . ? C11 C4 H4 108.6 . . ? C6 C5 C9 120.90(8) . . ? C6 C5 C4 121.37(8) . . ? C9 C5 C4 117.72(8) . . ? C5 C6 N1 122.27(8) . . ? C5 C6 H6 118.9 . . ? N1 C6 H6 118.9 . . ? O1 C7 C3 120.20(9) . . ? O1 C7 C8 120.04(9) . . ? C3 C7 C8 119.75(8) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C9 C5 119.89(9) . . ? O2 C9 C10 119.86(9) . . ? C5 C9 C10 120.25(8) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 117.74(8) . . ? C16 C11 C4 121.20(8) . . ? C12 C11 C4 121.03(8) . . ? C13 C12 C11 120.98(8) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C14 120.18(8) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? O3 C14 C15 124.14(8) . . ? O3 C14 C13 116.04(8) . . ? C15 C14 C13 119.82(8) . . ? C14 C15 C16 119.09(8) . . ? C14 C15 H15 120.5 . . ? C16 C15 H15 120.5 . . ? C11 C16 C15 122.11(8) . . ? C11 C16 H16 118.9 . . ? C15 C16 H16 118.9 . . ? O3 C17 H17A 109.5 . . ? O3 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O3 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C1 126.15(9) . . ? C19 C18 H18 116.9 . . ? C1 C18 H18 116.9 . . ? C18 C19 H19A 121.5(8) . . ? C18 C19 H19B 121.7(9) . . ? H19A C19 H19B 116.8(12) . . ? #===END data_4k _database_code_depnum_ccdc_archive 'CCDC 869488' #TrackingRef '- PRG.cif' _audit_creation_date 2011-11-30 _audit_creation_method ; Olex2 1.1-beta (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; 1,1'-(4-Ethyl-1-methyl-1,4-dihydropyridine-3,5-diyl)diethanone ; _chemical_formula_moiety 'C12 H17 N O2' _chemical_formula_sum 'C12 H17 N O2' _chemical_formula_weight 207.27 _chemical_absolute_configuration unk _chemical_melting_point 455.7(5) 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 33 _space_group_name_H-M_alt 'P n a 21' _space_group_name_Hall 'P 2c -2n' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, z+1/2' 3 '-x+1/2, y+1/2, z+1/2' 4 'x+1/2, -y+1/2, z' _cell_length_a 10.6949(3) _cell_length_b 9.1552(3) _cell_length_c 11.6695(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1142.61(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 6180 _cell_measurement_temperature 120 _cell_measurement_theta_max 29.985 _cell_measurement_theta_min 2.828 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_T_max 0.7460 _exptl_absorpt_correction_T_min 0.6316 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. R(int) was 0.0923 before and 0.0510 after correction. The Ratio of minimum to maximum transmission is 0.8466. The \l/2 correction factor is 0.0015. ; loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 1.00 1.00 0.1200 0.00 -1.00 -1.00 0.1200 0.00 1.00 -1.00 0.1350 0.00 -1.00 1.00 0.1350 1.00 0.00 0.00 0.3500 -1.00 0.00 0.00 0.3500 _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.205 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 448 _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.24 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of \w scans each set at different \f and/or 2\q angles and each scan (3 s exposure) covering -0.3\% in \w. The crystal to detector distance was 4.86 cm. ; _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_unetI/netI 0.0184 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 13623 _diffrn_reflns_theta_full 29.99 _diffrn_reflns_theta_max 29.99 _diffrn_reflns_theta_min 2.83 _diffrn_ambient_temperature 120 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'sealed X-ray tube' _diffrn_source_current 10.0 _diffrn_source_power 0.3 _diffrn_source_target Mo _diffrn_source_voltage 30.0 _diffrn_standards_number 0 _reflns_Friedel_coverage 0.86 _reflns_number_gt 1648 _reflns_number_total 1736 _reflns_threshold_expression I>2\s(I) _computing_cell_refinement 'SAINT v7.46A (Bruker, 2008)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v7.46A (Bruker, 2008)' _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 ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.370 _refine_diff_density_min -0.141 _refine_diff_density_rms 0.046 _refine_ls_abs_structure_details 'undeterminable, all \Df" set to 0, Friedel equivalents merged' _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 144 _refine_ls_number_reflns 1736 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0384 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0765P)^2^+0.1158P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1052 _refine_ls_wR_factor_ref 0.1077 _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. Methyl groups were refined as rigid bodies rotating around C---C bonds, with a common refined U for three H atoms. Other H atoms: riding model. Pseudo-centrosymmetric structure, but refinement in Pnma was unsuccessful: R1=0.096 and poor molecular geometry. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.41780(13) 0.30895(14) 0.78939(11) 0.0318(3) Uani 1 1 d . . . O2 O 0.39960(11) 0.31632(14) 0.36254(11) 0.0278(3) Uani 1 1 d . . . N1 N 0.12580(11) 0.02478(12) 0.58319(13) 0.0212(2) Uani 1 1 d . . . C1 C 0.01107(13) -0.06224(16) 0.58693(16) 0.0250(3) Uani 1 1 d . . . H1A H -0.0586 -0.0006 0.6121 0.049(4) Uiso 1 1 calc R . . H1B H 0.0218 -0.1434 0.6408 0.049(4) Uiso 1 1 calc R . . H1C H -0.0068 -0.1010 0.5104 0.049(4) Uiso 1 1 calc R . . C2 C 0.17848(14) 0.07480(17) 0.68348(13) 0.0207(3) Uani 1 1 d . . . H2 H 0.1380 0.0544 0.7542 0.025 Uiso 1 1 calc R . . C3 C 0.28645(13) 0.15225(16) 0.68418(13) 0.0192(3) Uani 1 1 d . . . C4 C 0.36152(12) 0.16486(14) 0.57459(14) 0.0189(3) Uani 1 1 d . . . H4 H 0.4091 0.2589 0.5754 0.023 Uiso 1 1 calc R . . C5 C 0.27076(14) 0.16603(15) 0.47504(13) 0.0192(3) Uani 1 1 d . . . C6 C 0.16377(13) 0.08694(16) 0.48165(13) 0.0197(3) Uani 1 1 d . . . H6 H 0.1141 0.0742 0.4149 0.024 Uiso 1 1 calc R . . C7 C 0.32764(15) 0.22503(18) 0.78920(14) 0.0247(3) Uani 1 1 d . . . C8 C 0.25568(19) 0.1999(2) 0.89953(15) 0.0352(4) Uani 1 1 d . . . H8A H 0.2986 0.2490 0.9629 0.051(4) Uiso 1 1 calc R . . H8B H 0.2509 0.0949 0.9152 0.051(4) Uiso 1 1 calc R . . H8C H 0.1710 0.2396 0.8917 0.051(4) Uiso 1 1 calc R . . C9 C 0.30248(13) 0.24319(17) 0.36920(13) 0.0201(3) Uani 1 1 d . . . C10 C 0.21408(14) 0.23469(19) 0.26867(14) 0.0254(3) Uani 1 1 d . . . H10A H 0.2493 0.2888 0.2038 0.040(4) Uiso 1 1 calc R . . H10B H 0.1334 0.2774 0.2901 0.040(4) Uiso 1 1 calc R . . H10C H 0.2021 0.1323 0.2468 0.040(4) Uiso 1 1 calc R . . C17 C 0.45404(13) 0.03688(17) 0.55958(14) 0.0245(3) Uani 1 1 d . . . H17A H 0.4061 -0.0556 0.5576 0.029 Uiso 1 1 calc R . . H17B H 0.4966 0.0476 0.4847 0.029 Uiso 1 1 calc R . . C18 C 0.55293(15) 0.0258(2) 0.65302(18) 0.0318(4) Uani 1 1 d . . . H18A H 0.6070 -0.0584 0.6379 0.048(4) Uiso 1 1 calc R . . H18B H 0.5120 0.0137 0.7276 0.048(4) Uiso 1 1 calc R . . H18C H 0.6034 0.1152 0.6537 0.048(4) 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 O1 0.0325(6) 0.0372(7) 0.0258(6) -0.0058(5) 0.0004(5) -0.0123(5) O2 0.0235(5) 0.0338(6) 0.0262(6) 0.0072(5) -0.0024(4) -0.0080(4) N1 0.0178(5) 0.0233(5) 0.0227(6) 0.0019(5) -0.0001(5) -0.0042(4) C1 0.0185(6) 0.0263(6) 0.0302(8) 0.0035(6) 0.0002(6) -0.0065(5) C2 0.0211(6) 0.0207(6) 0.0203(7) 0.0005(5) 0.0009(5) -0.0002(5) C3 0.0193(6) 0.0202(6) 0.0181(6) 0.0006(5) -0.0002(5) -0.0002(4) C4 0.0164(5) 0.0214(5) 0.0188(6) 0.0023(6) 0.0000(5) -0.0017(4) C5 0.0180(6) 0.0200(6) 0.0197(7) 0.0018(5) -0.0007(5) 0.0002(5) C6 0.0173(6) 0.0212(6) 0.0205(7) 0.0018(5) -0.0015(5) 0.0000(5) C7 0.0263(7) 0.0269(7) 0.0210(7) -0.0005(6) 0.0006(6) -0.0018(6) C8 0.0402(9) 0.0420(9) 0.0234(8) -0.0059(7) 0.0059(7) -0.0116(8) C9 0.0194(6) 0.0209(6) 0.0200(7) 0.0021(5) -0.0001(5) 0.0000(5) C10 0.0235(7) 0.0311(8) 0.0214(7) 0.0040(6) -0.0032(6) -0.0023(6) C17 0.0195(6) 0.0290(7) 0.0252(8) -0.0018(6) -0.0011(5) 0.0042(5) C18 0.0248(7) 0.0332(8) 0.0373(9) 0.0012(7) -0.0097(6) 0.0042(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 C7 1.233(2) . ? O2 C9 1.2382(18) . ? N1 C1 1.4636(17) . ? N1 C2 1.377(2) . ? N1 C6 1.376(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2 0.9500 . ? C2 C3 1.355(2) . ? C3 C4 1.514(2) . ? C3 C7 1.463(2) . ? C4 H4 1.0000 . ? C4 C5 1.514(2) . ? C4 C17 1.5436(19) . ? C5 C6 1.3563(19) . ? C5 C9 1.463(2) . ? C6 H6 0.9500 . ? C7 C8 1.518(2) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.509(2) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C17 C18 1.522(2) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? 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 N1 C1 119.91(14) . . ? C6 N1 C1 119.89(14) . . ? C6 N1 C2 118.26(11) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 H2 119.1 . . ? C3 C2 N1 121.85(13) . . ? C3 C2 H2 119.1 . . ? C2 C3 C4 119.12(13) . . ? C2 C3 C7 120.00(13) . . ? C7 C3 C4 120.87(12) . . ? C3 C4 H4 109.1 . . ? C3 C4 C17 112.20(12) . . ? C5 C4 C3 107.98(10) . . ? C5 C4 H4 109.1 . . ? C5 C4 C17 109.23(12) . . ? C17 C4 H4 109.1 . . ? C6 C5 C4 119.57(13) . . ? C6 C5 C9 120.10(14) . . ? C9 C5 C4 120.18(12) . . ? N1 C6 H6 119.4 . . ? C5 C6 N1 121.26(14) . . ? C5 C6 H6 119.4 . . ? O1 C7 C3 121.39(15) . . ? O1 C7 C8 119.30(15) . . ? C3 C7 C8 119.28(14) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C9 C5 120.58(13) . . ? O2 C9 C10 120.31(13) . . ? C5 C9 C10 119.10(12) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C4 C17 H17A 108.6 . . ? C4 C17 H17B 108.6 . . ? H17A C17 H17B 107.6 . . ? C18 C17 C4 114.48(13) . . ? C18 C17 H17A 108.6 . . ? C18 C17 H17B 108.6 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? #===END data_6 _database_code_depnum_ccdc_archive 'CCDC 869489' #TrackingRef '- PRG.cif' _audit_creation_date 2012-01-16 _audit_creation_method ; Olex2 1.1-beta (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; 1,1'-(2-Methoxy-4-(4-nitrophenyl)-1-phenyl-1,2,3,4-tetrahydropyridine-3,5-diyl) diethanone ; _chemical_formula_moiety 'C22 H22 N2 O5' _chemical_formula_sum 'C22 H22 N2 O5' _chemical_formula_weight 394.42 _chemical_melting_point 471 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 monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 11.9899(6) _cell_length_b 15.0103(8) _cell_length_c 10.9303(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.151(10) _cell_angle_gamma 90.00 _cell_volume 1947.28(18) _cell_formula_units_Z 4 _cell_measurement_reflns_used 8297 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 29.873 _cell_measurement_theta_min 2.188 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 832 _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.06 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of \w scans each set at different \f and/or 2\q angles and each scan (10 s exposure) covering -0.3\% in \w. The crystal to detector distance was 4.83 cm. ; loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1.00 0.00 0.00 0.0300 -1.00 0.00 0.00 0.0300 0.00 1.00 -1.00 0.1500 0.00 1.00 0.00 0.1500 0.00 -1.00 0.00 0.1500 0.00 0.00 1.00 0.2050 0.00 -1.00 -1.00 0.1700 _diffrn_reflns_av_R_equivalents 0.0407 _diffrn_reflns_av_unetI/netI 0.0266 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 24552 _diffrn_reflns_theta_full 28.50 _diffrn_reflns_theta_max 28.50 _diffrn_reflns_theta_min 1.72 _diffrn_ambient_temperature 120(2) _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'sealed X-ray tube' _diffrn_source_current 35.0 _diffrn_source_power 1.75 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _reflns_number_gt 3804 _reflns_number_total 4928 _reflns_threshold_expression I>2\s(I) _computing_cell_refinement 'SAINT v7.46A (Bruker, 2008)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v7.46A (Bruker, 2008)' _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 ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.328 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.044 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 268 _refine_ls_number_reflns 4928 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0402 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0686P)^2^+0.1309P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1102 _refine_ls_wR_factor_ref 0.1177 _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. Methyl groups were refined as rigid bodies rotating around C---C or O---C bonds, with a common refined U for three H atoms. Other H atoms: riding model. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 -0.02958(7) 0.44774(5) 0.17930(8) 0.0291(2) Uani 1 1 d . . . O2 O 0.18969(8) 0.74788(6) 0.10437(9) 0.0397(2) Uani 1 1 d . . . O3 O 0.27488(9) 0.26466(6) 0.70120(9) 0.0437(3) Uani 1 1 d . . . O4 O 0.22521(9) 0.37258(7) 0.81155(8) 0.0449(3) Uani 1 1 d . . . O5 O 0.40289(7) 0.56944(6) 0.31039(8) 0.0346(2) Uani 1 1 d . . . N1 N 0.31281(8) 0.57959(6) 0.10883(9) 0.0273(2) Uani 1 1 d . . . N2 N 0.24154(9) 0.34095(7) 0.71214(9) 0.0299(2) Uani 1 1 d . . . C1 C 0.45188(15) 0.61505(11) 0.41914(15) 0.0502(4) Uani 1 1 d . . . H1A H 0.4847 0.6713 0.3962 0.069(3) Uiso 1 1 d R . . H1B H 0.5109 0.5779 0.4648 0.069(3) Uiso 1 1 d R . . H1C H 0.3936 0.6273 0.4714 0.069(3) Uiso 1 1 d R . . C2 C 0.22525(9) 0.52175(7) 0.08487(10) 0.0246(2) Uani 1 1 d . . . H2 H 0.2193 0.4885 0.0103 0.030 Uiso 1 1 d R . . C3 C 0.14598(10) 0.50809(7) 0.15938(10) 0.0238(2) Uani 1 1 d . . . C4 C 0.14697(10) 0.55975(7) 0.27730(10) 0.0252(2) Uani 1 1 d . . . H4 H 0.0680 0.5805 0.2790 0.030 Uiso 1 1 d R . . C5 C 0.22001(11) 0.64455(7) 0.27349(11) 0.0286(3) Uani 1 1 d . . . H5 H 0.2374 0.6679 0.3598 0.034 Uiso 1 1 d R . . C6 C 0.33178(11) 0.62492(8) 0.22701(11) 0.0289(3) Uani 1 1 d . . . H6 H 0.3715 0.6825 0.2169 0.035 Uiso 1 1 d R . . C7 C 0.05417(10) 0.44519(7) 0.12625(10) 0.0240(2) Uani 1 1 d . . . C8 C 0.06367(11) 0.37515(7) 0.02945(11) 0.0274(2) Uani 1 1 d . . . H8A H -0.0066 0.3410 0.0145 0.036(2) Uiso 1 1 d R . . H8B H 0.1262 0.3349 0.0584 0.036(2) Uiso 1 1 d R . . H8C H 0.0775 0.4039 -0.0475 0.036(2) Uiso 1 1 d R . . C9 C 0.15493(11) 0.71684(8) 0.19453(12) 0.0325(3) Uani 1 1 d . . . C10 C 0.04718(13) 0.74885(9) 0.23480(14) 0.0442(3) Uani 1 1 d . . . H10A H -0.0151 0.7106 0.1987 0.088(4) Uiso 1 1 d R . . H10B H 0.0325 0.8104 0.2067 0.088(4) Uiso 1 1 d R . . H10C H 0.0538 0.7466 0.3251 0.088(4) Uiso 1 1 d R . . C11 C 0.37933(10) 0.60085(8) 0.01456(12) 0.0280(3) Uani 1 1 d . . . C12 C 0.32944(11) 0.60488(8) -0.10810(12) 0.0310(3) Uani 1 1 d . . . H12 H 0.2505 0.5964 -0.1287 0.037 Uiso 1 1 d R . . C13 C 0.39521(12) 0.62126(9) -0.20042(13) 0.0366(3) Uani 1 1 d . . . H13 H 0.3614 0.6221 -0.2844 0.044 Uiso 1 1 d R . . C14 C 0.50967(12) 0.63639(9) -0.17085(14) 0.0384(3) Uani 1 1 d . . . H14 H 0.5546 0.6474 -0.2342 0.046 Uiso 1 1 d R . . C15 C 0.55808(11) 0.63530(8) -0.04827(14) 0.0373(3) Uani 1 1 d . . . H15 H 0.6363 0.6474 -0.0277 0.045 Uiso 1 1 d R . . C16 C 0.49434(11) 0.61692(8) 0.04510(13) 0.0328(3) Uani 1 1 d . . . H16 H 0.5287 0.6153 0.1289 0.039 Uiso 1 1 d R . . C17 C 0.17842(10) 0.50240(7) 0.39269(10) 0.0247(2) Uani 1 1 d . . . C18 C 0.15357(11) 0.53298(8) 0.50609(11) 0.0302(3) Uani 1 1 d . . . H18 H 0.1220 0.5907 0.5113 0.036 Uiso 1 1 d R . . C19 C 0.17412(11) 0.48067(8) 0.61178(11) 0.0310(3) Uani 1 1 d . . . H19 H 0.1572 0.5019 0.6889 0.037 Uiso 1 1 d R . . C20 C 0.21985(10) 0.39706(8) 0.60151(10) 0.0254(2) Uani 1 1 d . . . C21 C 0.24581(10) 0.36412(8) 0.49045(11) 0.0277(2) Uani 1 1 d . . . H21 H 0.2770 0.3063 0.4858 0.033 Uiso 1 1 d R . . C22 C 0.22498(10) 0.41764(8) 0.38641(11) 0.0278(3) Uani 1 1 d . . . H22 H 0.2427 0.3963 0.3096 0.033 Uiso 1 1 d 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 O1 0.0325(4) 0.0270(4) 0.0296(4) 0.0001(3) 0.0107(4) -0.0015(3) O2 0.0482(6) 0.0292(5) 0.0411(5) 0.0074(4) 0.0040(4) -0.0015(4) O3 0.0604(7) 0.0377(5) 0.0342(5) 0.0083(4) 0.0111(5) 0.0113(5) O4 0.0591(7) 0.0558(6) 0.0217(4) 0.0024(4) 0.0120(4) 0.0105(5) O5 0.0359(5) 0.0325(5) 0.0329(5) 0.0051(4) -0.0038(4) -0.0033(4) N1 0.0298(5) 0.0249(5) 0.0275(5) 0.0000(4) 0.0048(4) -0.0032(4) N2 0.0287(5) 0.0381(6) 0.0237(5) 0.0032(4) 0.0061(4) -0.0007(4) C1 0.0511(9) 0.0527(9) 0.0411(8) 0.0032(7) -0.0136(7) -0.0083(7) C2 0.0301(6) 0.0198(5) 0.0237(5) -0.0007(4) 0.0028(4) -0.0001(4) C3 0.0300(6) 0.0196(5) 0.0219(5) 0.0005(4) 0.0040(4) 0.0006(4) C4 0.0313(6) 0.0214(5) 0.0231(5) -0.0024(4) 0.0043(5) 0.0004(4) C5 0.0386(7) 0.0218(5) 0.0248(6) -0.0031(4) 0.0027(5) -0.0029(5) C6 0.0345(6) 0.0230(5) 0.0280(6) 0.0012(4) 0.0002(5) -0.0047(5) C7 0.0306(6) 0.0207(5) 0.0210(5) 0.0034(4) 0.0050(4) 0.0003(4) C8 0.0350(6) 0.0231(5) 0.0249(6) -0.0015(4) 0.0072(5) -0.0037(4) C9 0.0426(7) 0.0194(5) 0.0346(7) -0.0058(5) 0.0019(6) -0.0022(5) C10 0.0575(9) 0.0295(7) 0.0465(8) -0.0080(6) 0.0107(7) 0.0118(6) C11 0.0301(6) 0.0221(5) 0.0329(6) 0.0017(4) 0.0079(5) -0.0010(4) C12 0.0293(6) 0.0301(6) 0.0344(7) 0.0019(5) 0.0074(5) -0.0012(5) C13 0.0412(7) 0.0357(7) 0.0345(7) 0.0016(5) 0.0108(6) -0.0028(5) C14 0.0393(7) 0.0333(7) 0.0465(8) 0.0035(6) 0.0197(6) -0.0007(5) C15 0.0276(6) 0.0300(6) 0.0557(9) 0.0050(6) 0.0108(6) -0.0010(5) C16 0.0303(6) 0.0281(6) 0.0395(7) 0.0047(5) 0.0026(5) -0.0006(5) C17 0.0276(6) 0.0238(5) 0.0231(5) -0.0024(4) 0.0046(4) -0.0021(4) C18 0.0391(7) 0.0262(6) 0.0262(6) -0.0049(5) 0.0071(5) 0.0031(5) C19 0.0384(7) 0.0341(6) 0.0217(5) -0.0052(5) 0.0088(5) 0.0006(5) C20 0.0261(6) 0.0307(6) 0.0198(5) 0.0009(4) 0.0041(4) -0.0022(4) C21 0.0329(6) 0.0259(5) 0.0250(6) -0.0008(4) 0.0066(5) 0.0038(4) C22 0.0348(6) 0.0279(6) 0.0221(5) -0.0027(4) 0.0081(5) 0.0028(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 O1 C7 1.2293(14) . ? O2 C9 1.2159(16) . ? O3 N2 1.2243(14) . ? O4 N2 1.2266(13) . ? O5 C1 1.4243(17) . ? O5 C6 1.4250(15) . ? N1 C2 1.3588(15) . ? N1 C6 1.4491(15) . ? N1 C11 1.4257(15) . ? N2 C20 1.4664(15) . ? C1 H1A 0.9793 . ? C1 H1B 0.9803 . ? C1 H1C 0.9805 . ? C2 H2 0.9498 . ? C2 C3 1.3520(16) . ? C3 C4 1.5028(15) . ? C3 C7 1.4564(16) . ? C4 H4 0.9999 . ? C4 C5 1.5489(16) . ? C4 C17 1.5294(15) . ? C5 H5 1.0000 . ? C5 C6 1.5277(18) . ? C5 C9 1.5297(17) . ? C6 H6 1.0000 . ? C7 C8 1.5073(15) . ? C8 H8A 0.9803 . ? C8 H8B 0.9800 . ? C8 H8C 0.9798 . ? C9 C10 1.502(2) . ? C10 H10A 0.9795 . ? C10 H10B 0.9810 . ? C10 H10C 0.9797 . ? C11 C12 1.3898(18) . ? C11 C16 1.3930(18) . ? C12 H12 0.9500 . ? C12 C13 1.3878(18) . ? C13 H13 0.9500 . ? C13 C14 1.383(2) . ? C14 H14 0.9500 . ? C14 C15 1.383(2) . ? C15 H15 0.9500 . ? C15 C16 1.3867(19) . ? C16 H16 0.9500 . ? C17 C18 1.3930(16) . ? C17 C22 1.3950(16) . ? C18 H18 0.9500 . ? C18 C19 1.3896(17) . ? C19 H19 0.9499 . ? C19 C20 1.3805(17) . ? C20 C21 1.3863(16) . ? C21 H21 0.9500 . ? C21 C22 1.3858(16) . ? C22 H22 0.9501 . ? 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 O5 C6 113.04(10) . . ? C2 N1 C6 119.41(10) . . ? C2 N1 C11 119.99(10) . . ? C11 N1 C6 120.39(9) . . ? O3 N2 O4 122.95(10) . . ? O3 N2 C20 118.61(10) . . ? O4 N2 C20 118.44(10) . . ? O5 C1 H1A 109.5 . . ? O5 C1 H1B 109.5 . . ? O5 C1 H1C 109.4 . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.4 . . ? N1 C2 H2 117.6 . . ? C3 C2 N1 124.80(10) . . ? C3 C2 H2 117.6 . . ? C2 C3 C4 121.17(10) . . ? C2 C3 C7 121.31(10) . . ? C7 C3 C4 117.49(10) . . ? C3 C4 H4 106.5 . . ? C3 C4 C5 109.68(9) . . ? C3 C4 C17 112.83(9) . . ? C5 C4 H4 106.5 . . ? C17 C4 H4 106.5 . . ? C17 C4 C5 114.23(9) . . ? C4 C5 H5 107.8 . . ? C6 C5 C4 112.11(9) . . ? C6 C5 H5 107.8 . . ? C6 C5 C9 110.51(10) . . ? C9 C5 C4 110.67(10) . . ? C9 C5 H5 107.8 . . ? O5 C6 N1 107.44(9) . . ? O5 C6 C5 111.93(10) . . ? O5 C6 H6 108.9 . . ? N1 C6 C5 110.66(10) . . ? N1 C6 H6 108.9 . . ? C5 C6 H6 108.9 . . ? O1 C7 C3 120.11(10) . . ? O1 C7 C8 120.06(10) . . ? C3 C7 C8 119.80(10) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8B 109.4 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C9 C5 121.54(12) . . ? O2 C9 C10 121.53(12) . . ? C10 C9 C5 116.92(11) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10B 109.4 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.4 . . ? C12 C11 N1 119.90(11) . . ? C12 C11 C16 119.98(12) . . ? C16 C11 N1 120.12(11) . . ? C11 C12 H12 120.1 . . ? C13 C12 C11 119.86(12) . . ? C13 C12 H12 120.1 . . ? C12 C13 H13 119.8 . . ? C14 C13 C12 120.42(13) . . ? C14 C13 H13 119.8 . . ? C13 C14 H14 120.3 . . ? C15 C14 C13 119.39(13) . . ? C15 C14 H14 120.3 . . ? C14 C15 H15 119.4 . . ? C14 C15 C16 121.07(12) . . ? C16 C15 H15 119.5 . . ? C11 C16 H16 120.4 . . ? C15 C16 C11 119.23(13) . . ? C15 C16 H16 120.4 . . ? C18 C17 C4 119.31(10) . . ? C18 C17 C22 118.81(11) . . ? C22 C17 C4 121.76(10) . . ? C17 C18 H18 119.4 . . ? C19 C18 C17 121.23(11) . . ? C19 C18 H18 119.4 . . ? C18 C19 H19 120.9 . . ? C20 C19 C18 118.14(10) . . ? C20 C19 H19 120.9 . . ? C19 C20 N2 118.76(10) . . ? C19 C20 C21 122.45(11) . . ? C21 C20 N2 118.79(10) . . ? C20 C21 H21 120.8 . . ? C22 C21 C20 118.36(11) . . ? C22 C21 H21 120.8 . . ? C17 C22 H22 119.5 . . ? C21 C22 C17 121.01(10) . . ? C21 C22 H22 119.5 . . ? #===END