# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Mattson1860 _audit_creation_date 2011-10-27T14:21:27-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 'Mattson 1860' _chemical_formula_moiety 'C24 H22 N2 O5' _chemical_formula_sum 'C24 H22 N2 O5' _chemical_formula_weight 418.44 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.4338(1) _cell_length_b 15.4596(3) _cell_length_c 15.6357(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2038.63(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2673 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description 'rectangular block' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_special_details ;All work was done at 150 K using an Oxford Cryosystems Cryostream Cooler. The data collection strategy was set up to measure an octant of reciprocal space with a redundancy factor of 4.0, which means that 90% of these reflections were measured at least 4.0 times. Phi and omega scans with a frame width of 1.0 degree were used. Data integration was done with Denzo, and scaling and merging of the data was done with Scalepack. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.10519 _diffrn_orient_matrix_ub_12 0.298416E-1 _diffrn_orient_matrix_ub_13 0.7471E-3 _diffrn_orient_matrix_ub_21 0.97808E-2 _diffrn_orient_matrix_ub_22 0.8643E-2 _diffrn_orient_matrix_ub_23 0.631628E-1 _diffrn_orient_matrix_ub_31 0.538376E-1 _diffrn_orient_matrix_ub_32 0.567353E-1 _diffrn_orient_matrix_ub_33 -0.100152E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_av_unetI/netI 0.033 _diffrn_reflns_number 27402 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 4629 _reflns_number_gt 3972 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ;For the methyl group, the hydrogen atoms were added at calculated positions using a riding model with U(H) = 1.5*Ueq(bonded carbon atom). The torsion angle, which defines the orientation of the methyl group about the O-C bond, was refined. The rest of the hydrogen atoms were included in the model at calculated positions using a riding model with U(H) = 1.2*Ueq(bonded atom). 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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0353P)^2^+0.2348P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4629 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0469 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0761 _refine_ls_wR_factor_gt 0.0715 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.142 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.037 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 C 0.80427(16) 0.67984(9) 0.22388(9) 0.0227(3) Uani 1 1 d . . . H1 H 0.8768 0.7256 0.2466 0.027 Uiso 1 1 calc R . . C2 C 0.70834(16) 0.64038(9) 0.29706(9) 0.0228(3) Uani 1 1 d . . . H2A H 0.6491 0.6864 0.3273 0.027 Uiso 1 1 calc R . . H2B H 0.6308 0.5984 0.2739 0.027 Uiso 1 1 calc R . . C3 C 0.81954(16) 0.59487(9) 0.35931(8) 0.0209(3) Uani 1 1 d . . . C4 C 0.93064(16) 0.52960(9) 0.31356(9) 0.0210(3) Uani 1 1 d . . . H4 H 1.0148 0.5147 0.3561 0.025 Uiso 1 1 calc R . . C5 C 0.69893(16) 0.71734(9) 0.15586(9) 0.0218(3) Uani 1 1 d . . . C6 C 0.59222(18) 0.66569(10) 0.11079(9) 0.0284(3) Uani 1 1 d . . . H6 H 0.5877 0.6053 0.1218 0.034 Uiso 1 1 calc R . . C7 C 0.49274(19) 0.70195(11) 0.05010(10) 0.0329(4) Uani 1 1 d . . . H7 H 0.4211 0.6662 0.0193 0.039 Uiso 1 1 calc R . . C8 C 0.4973(2) 0.79004(12) 0.03421(10) 0.0364(4) Uani 1 1 d . . . H8 H 0.4285 0.8149 -0.0072 0.044 Uiso 1 1 calc R . . C9 C 0.60235(19) 0.84154(11) 0.07876(10) 0.0345(4) Uani 1 1 d . . . H9 H 0.6056 0.902 0.0681 0.041 Uiso 1 1 calc R . . C10 C 0.70323(18) 0.80553(9) 0.13905(10) 0.0274(3) Uani 1 1 d . . . H10 H 0.7758 0.8414 0.1691 0.033 Uiso 1 1 calc R . . C11 C 0.92346(16) 0.65798(9) 0.41212(9) 0.0230(3) Uani 1 1 d . . . C12 C 0.91943(19) 0.78730(11) 0.49317(11) 0.0360(4) Uani 1 1 d . . . H12A H 0.9836 0.8238 0.4554 0.054 Uiso 1 1 calc R . . H12B H 0.9886 0.7581 0.5345 0.054 Uiso 1 1 calc R . . H12C H 0.8425 0.8233 0.5238 0.054 Uiso 1 1 calc R . . C13 C 0.85982(16) 0.44355(9) 0.28509(9) 0.0224(3) Uani 1 1 d . . . C14 C 0.86489(19) 0.37489(10) 0.34272(10) 0.0302(3) Uani 1 1 d . . . H14 H 0.9032 0.3846 0.399 0.036 Uiso 1 1 calc R . . C15 C 0.81510(19) 0.29256(10) 0.31958(11) 0.0364(4) Uani 1 1 d . . . H15 H 0.8179 0.2468 0.3601 0.044 Uiso 1 1 calc R . . C16 C 0.76124(18) 0.27742(10) 0.23714(12) 0.0351(4) Uani 1 1 d . . . H16 H 0.728 0.2211 0.2206 0.042 Uiso 1 1 calc R . . C17 C 0.75639(18) 0.34463(10) 0.17942(11) 0.0319(4) Uani 1 1 d . . . H17 H 0.7197 0.3342 0.1229 0.038 Uiso 1 1 calc R . . C18 C 0.80432(17) 0.42768(10) 0.20241(9) 0.0261(3) Uani 1 1 d . . . H18 H 0.7992 0.4734 0.1619 0.031 Uiso 1 1 calc R . . C19 C 1.13675(16) 0.54025(9) 0.20404(9) 0.0220(3) Uani 1 1 d . . . C20 C 1.26543(17) 0.51255(9) 0.25328(10) 0.0268(3) Uani 1 1 d . . . H20 H 1.2672 0.5233 0.3131 0.032 Uiso 1 1 calc R . . C21 C 1.39009(17) 0.46947(10) 0.21473(10) 0.0302(4) Uani 1 1 d . . . H21 H 1.4759 0.4491 0.2486 0.036 Uiso 1 1 calc R . . C22 C 1.39112(18) 0.45570(10) 0.12747(10) 0.0314(4) Uani 1 1 d . . . H22 H 1.4768 0.4258 0.1014 0.038 Uiso 1 1 calc R . . C23 C 1.26646(18) 0.48579(10) 0.07839(10) 0.0329(4) Uani 1 1 d . . . H23 H 1.2683 0.4778 0.0182 0.039 Uiso 1 1 calc R . . C24 C 1.13844(18) 0.52768(10) 0.11616(9) 0.0285(3) Uani 1 1 d . . . H24 H 1.0527 0.5476 0.082 0.034 Uiso 1 1 calc R . . N1 N 1.00994(13) 0.58300(7) 0.24747(7) 0.0214(2) Uani 1 1 d . . . N2 N 0.72216(14) 0.54658(7) 0.42705(8) 0.0247(3) Uani 1 1 d . . . O1 O 0.89558(11) 0.61186(6) 0.18444(6) 0.0228(2) Uani 1 1 d . . . O2 O 1.06258(12) 0.64904(7) 0.42534(7) 0.0321(3) Uani 1 1 d . . . O3 O 0.83522(12) 0.72260(6) 0.44225(7) 0.0298(2) Uani 1 1 d . . . O4 O 0.58014(12) 0.53861(7) 0.41699(7) 0.0365(3) Uani 1 1 d . . . O5 O 0.79580(13) 0.51846(8) 0.48840(7) 0.0372(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0233(7) 0.0210(7) 0.0239(7) -0.0017(6) -0.0009(6) 0.0029(6) C2 0.0217(7) 0.0257(7) 0.0211(7) -0.0005(6) -0.0005(6) 0.0030(6) C3 0.0216(7) 0.0224(7) 0.0188(7) 0.0008(6) 0.0015(5) 0.0000(6) C4 0.0218(7) 0.0235(7) 0.0177(7) 0.0022(6) 0.0016(5) 0.0014(5) C5 0.0220(7) 0.0240(7) 0.0194(7) -0.0002(6) 0.0032(6) 0.0050(6) C6 0.0302(8) 0.0287(8) 0.0263(8) 0.0002(7) 0.0000(6) 0.0017(6) C7 0.0302(8) 0.0441(10) 0.0245(8) -0.0010(7) -0.0044(6) 0.0007(7) C8 0.0326(8) 0.0488(11) 0.0279(8) 0.0081(7) -0.0034(7) 0.0123(8) C9 0.0399(9) 0.0297(8) 0.0339(9) 0.0063(7) -0.0013(7) 0.0081(7) C10 0.0287(8) 0.0252(8) 0.0283(8) 0.0006(6) 0.0006(6) 0.0027(6) C11 0.0254(8) 0.0260(7) 0.0174(7) 0.0022(6) 0.0000(6) -0.0007(6) C12 0.0350(8) 0.0318(9) 0.0413(10) -0.0145(8) 0.0013(7) -0.0066(7) C13 0.0192(7) 0.0228(7) 0.0251(7) 0.0002(6) 0.0042(6) 0.0029(6) C14 0.0343(8) 0.0284(8) 0.0278(8) 0.0031(7) 0.0037(7) 0.0051(7) C15 0.0386(9) 0.0256(8) 0.0450(10) 0.0074(8) 0.0083(8) 0.0028(7) C16 0.0295(8) 0.0231(7) 0.0527(11) -0.0042(7) 0.0039(8) 0.0002(6) C17 0.0276(8) 0.0295(8) 0.0385(9) -0.0078(7) -0.0023(7) 0.0013(7) C18 0.0253(7) 0.0251(7) 0.0279(8) 0.0011(6) 0.0006(6) 0.0031(6) C19 0.0223(7) 0.0189(7) 0.0247(8) 0.0011(6) 0.0038(6) -0.0006(6) C20 0.0246(7) 0.0305(8) 0.0251(8) 0.0016(6) 0.0016(6) 0.0002(6) C21 0.0218(7) 0.0316(9) 0.0372(9) 0.0059(7) 0.0025(6) 0.0033(6) C22 0.0252(8) 0.0314(8) 0.0376(9) 0.0001(7) 0.0085(7) 0.0053(6) C23 0.0335(8) 0.0388(8) 0.0264(8) -0.0027(7) 0.0074(7) 0.0027(7) C24 0.0267(8) 0.0321(8) 0.0266(8) 0.0036(7) 0.0025(6) 0.0035(6) N1 0.0192(6) 0.0249(6) 0.0201(6) 0.0037(5) 0.0000(5) 0.0048(5) N2 0.0275(7) 0.0248(6) 0.0219(6) -0.0014(5) 0.0031(5) -0.0004(5) O1 0.0237(5) 0.0249(5) 0.0197(5) 0.0018(4) -0.0017(4) 0.0065(4) O2 0.0250(6) 0.0380(6) 0.0334(6) -0.0062(5) -0.0075(5) 0.0023(5) O3 0.0269(5) 0.0278(6) 0.0346(6) -0.0105(5) -0.0002(4) 0.0000(4) O4 0.0245(6) 0.0451(7) 0.0399(6) 0.0050(6) 0.0030(5) -0.0072(5) O5 0.0399(6) 0.0486(7) 0.0232(6) 0.0105(5) -0.0013(5) -0.0007(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.4415(16) . ? C1 C5 1.5021(19) . ? C1 C2 1.5284(19) . ? C1 H1 1 . ? C2 C3 1.5238(19) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 N2 1.5341(18) . ? C3 C11 1.5498(19) . ? C3 C4 1.5517(19) . ? C4 N1 1.4822(17) . ? C4 C13 1.5247(19) . ? C4 H4 1 . ? C5 C10 1.389(2) . ? C5 C6 1.394(2) . ? C6 C7 1.385(2) . ? C6 H6 0.95 . ? C7 C8 1.385(2) . ? C7 H7 0.95 . ? C8 C9 1.380(2) . ? C8 H8 0.95 . ? C9 C10 1.386(2) . ? C9 H9 0.95 . ? C10 H10 0.95 . ? C11 O2 1.1994(17) . ? C11 O3 1.3317(17) . ? C12 O3 1.4624(18) . ? C12 H12A 0.98 . ? C12 H12B 0.98 . ? C12 H12C 0.98 . ? C13 C14 1.393(2) . ? C13 C18 1.397(2) . ? C14 C15 1.388(2) . ? C14 H14 0.95 . ? C15 C16 1.387(2) . ? C15 H15 0.95 . ? C16 C17 1.377(2) . ? C16 H16 0.95 . ? C17 C18 1.393(2) . ? C17 H17 0.95 . ? C18 H18 0.95 . ? C19 C24 1.388(2) . ? C19 C20 1.398(2) . ? C19 N1 1.4289(17) . ? C20 C21 1.383(2) . ? C20 H20 0.95 . ? C21 C22 1.381(2) . ? C21 H21 0.95 . ? C22 C23 1.382(2) . ? C22 H22 0.95 . ? C23 C24 1.391(2) . ? C23 H23 0.95 . ? C24 H24 0.95 . ? N1 O1 1.4494(14) . ? N2 O4 1.2143(15) . ? N2 O5 1.2227(16) . ? 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 O1 C1 C5 107.12(11) . . ? O1 C1 C2 108.18(11) . . ? C5 C1 C2 111.78(11) . . ? O1 C1 H1 109.9 . . ? C5 C1 H1 109.9 . . ? C2 C1 H1 109.9 . . ? C3 C2 C1 109.68(11) . . ? C3 C2 H2A 109.7 . . ? C1 C2 H2A 109.7 . . ? C3 C2 H2B 109.7 . . ? C1 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C2 C3 N2 109.64(11) . . ? C2 C3 C11 113.44(11) . . ? N2 C3 C11 103.96(10) . . ? C2 C3 C4 112.18(11) . . ? N2 C3 C4 108.96(10) . . ? C11 C3 C4 108.27(11) . . ? N1 C4 C13 117.34(11) . . ? N1 C4 C3 103.39(10) . . ? C13 C4 C3 117.74(11) . . ? N1 C4 H4 105.8 . . ? C13 C4 H4 105.8 . . ? C3 C4 H4 105.8 . . ? C10 C5 C6 118.90(13) . . ? C10 C5 C1 119.83(13) . . ? C6 C5 C1 121.24(13) . . ? C7 C6 C5 120.36(15) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C8 C7 C6 120.27(15) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C9 C8 C7 119.65(15) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C10 120.37(15) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C9 C10 C5 120.45(14) . . ? C9 C10 H10 119.8 . . ? C5 C10 H10 119.8 . . ? O2 C11 O3 124.90(13) . . ? O2 C11 C3 124.92(13) . . ? O3 C11 C3 110.16(11) . . ? O3 C12 H12A 109.5 . . ? O3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 118.38(13) . . ? C14 C13 C4 117.64(13) . . ? C18 C13 C4 123.70(12) . . ? C15 C14 C13 121.38(15) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C16 C15 C14 119.74(15) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C17 C16 C15 119.45(15) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C16 C17 C18 121.17(15) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? C17 C18 C13 119.86(14) . . ? C17 C18 H18 120.1 . . ? C13 C18 H18 120.1 . . ? C24 C19 C20 119.63(13) . . ? C24 C19 N1 122.89(13) . . ? C20 C19 N1 117.45(12) . . ? C21 C20 C19 119.85(14) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C22 C21 C20 120.65(14) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C21 C22 C23 119.46(14) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? C22 C23 C24 120.76(15) . . ? C22 C23 H23 119.6 . . ? C24 C23 H23 119.6 . . ? C19 C24 C23 119.58(14) . . ? C19 C24 H24 120.2 . . ? C23 C24 H24 120.2 . . ? C19 N1 O1 108.50(10) . . ? C19 N1 C4 114.29(10) . . ? O1 N1 C4 110.20(10) . . ? O4 N2 O5 124.51(13) . . ? O4 N2 C3 119.21(12) . . ? O5 N2 C3 116.28(11) . . ? C1 O1 N1 106.80(9) . . ? C11 O3 C12 115.74(11) . . ? 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 O1 C1 C2 C3 56.24(14) . . . . ? C5 C1 C2 C3 173.94(11) . . . . ? C1 C2 C3 N2 -173.59(11) . . . . ? C1 C2 C3 C11 70.69(14) . . . . ? C1 C2 C3 C4 -52.39(15) . . . . ? C2 C3 C4 N1 55.35(13) . . . . ? N2 C3 C4 N1 176.94(10) . . . . ? C11 C3 C4 N1 -70.59(13) . . . . ? C2 C3 C4 C13 -75.84(15) . . . . ? N2 C3 C4 C13 45.75(15) . . . . ? C11 C3 C4 C13 158.22(11) . . . . ? O1 C1 C5 C10 -124.90(13) . . . . ? C2 C1 C5 C10 116.76(14) . . . . ? O1 C1 C5 C6 57.28(16) . . . . ? C2 C1 C5 C6 -61.06(17) . . . . ? C10 C5 C6 C7 0.2(2) . . . . ? C1 C5 C6 C7 178.05(14) . . . . ? C5 C6 C7 C8 -0.6(2) . . . . ? C6 C7 C8 C9 0.4(3) . . . . ? C7 C8 C9 C10 0.1(2) . . . . ? C8 C9 C10 C5 -0.5(2) . . . . ? C6 C5 C10 C9 0.3(2) . . . . ? C1 C5 C10 C9 -177.52(13) . . . . ? C2 C3 C11 O2 -135.63(15) . . . . ? N2 C3 C11 O2 105.34(16) . . . . ? C4 C3 C11 O2 -10.43(19) . . . . ? C2 C3 C11 O3 45.71(15) . . . . ? N2 C3 C11 O3 -73.32(13) . . . . ? C4 C3 C11 O3 170.91(11) . . . . ? N1 C4 C13 C14 145.50(12) . . . . ? C3 C4 C13 C14 -90.00(15) . . . . ? N1 C4 C13 C18 -28.25(19) . . . . ? C3 C4 C13 C18 96.26(16) . . . . ? C18 C13 C14 C15 -0.5(2) . . . . ? C4 C13 C14 C15 -174.62(13) . . . . ? C13 C14 C15 C16 1.0(2) . . . . ? C14 C15 C16 C17 -0.6(2) . . . . ? C15 C16 C17 C18 -0.2(2) . . . . ? C16 C17 C18 C13 0.6(2) . . . . ? C14 C13 C18 C17 -0.3(2) . . . . ? C4 C13 C18 C17 173.45(13) . . . . ? C24 C19 C20 C21 -2.9(2) . . . . ? N1 C19 C20 C21 178.86(13) . . . . ? C19 C20 C21 C22 1.9(2) . . . . ? C20 C21 C22 C23 0.3(2) . . . . ? C21 C22 C23 C24 -1.7(2) . . . . ? C20 C19 C24 C23 1.6(2) . . . . ? N1 C19 C24 C23 179.72(13) . . . . ? C22 C23 C24 C19 0.7(2) . . . . ? C24 C19 N1 O1 -2.45(18) . . . . ? C20 C19 N1 O1 175.75(11) . . . . ? C24 C19 N1 C4 120.95(14) . . . . ? C20 C19 N1 C4 -60.85(16) . . . . ? C13 C4 N1 C19 -57.24(15) . . . . ? C3 C4 N1 C19 171.33(11) . . . . ? C13 C4 N1 O1 65.24(14) . . . . ? C3 C4 N1 O1 -66.19(12) . . . . ? C2 C3 N2 O4 10.96(16) . . . . ? C11 C3 N2 O4 132.56(13) . . . . ? C4 C3 N2 O4 -112.16(13) . . . . ? C2 C3 N2 O5 -169.06(12) . . . . ? C11 C3 N2 O5 -47.46(15) . . . . ? C4 C3 N2 O5 67.82(14) . . . . ? C5 C1 O1 N1 173.34(10) . . . . ? C2 C1 O1 N1 -66.00(12) . . . . ? C19 N1 O1 C1 -159.20(10) . . . . ? C4 N1 O1 C1 74.97(12) . . . . ? O2 C11 O3 C12 1.6(2) . . . . ? C3 C11 O3 C12 -179.73(12) . . . . ? # END of CIF _database_code_depnum_ccdc_archive 'CCDC 936756' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Mattson1934 _audit_creation_date 2013-02-27T17:49:38-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 'Mattson 1934' _chemical_formula_moiety 'C24 H22 N2 O5' _chemical_formula_sum 'C24 H22 N2 O5' _chemical_formula_weight 418.44 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2132(1) _cell_length_b 8.7380(1) _cell_length_c 15.5338(3) _cell_angle_alpha 84.567(1) _cell_angle_beta 79.398(1) _cell_angle_gamma 67.733(1) _cell_volume 1013.69(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4589 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description 'triangular plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_special_details ;All work was done at 150 K using an Oxford Cryosystems Cryostream Cooler. The data collection strategy was set up to measure a hemisphere of reciprocal space with a redundancy factor of 3.5, which means that 90% of these reflections were measured at least 3.5 times. Phi and omega scans with a frame width of 1.0 degree were used. Data integration was done with Denzo, and scaling and merging of the data was done with Scalepack. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.897 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.886911E-1 _diffrn_orient_matrix_ub_12 0.01525 _diffrn_orient_matrix_ub_13 -0.501322E-1 _diffrn_orient_matrix_ub_21 0.665067E-1 _diffrn_orient_matrix_ub_22 0.224084E-1 _diffrn_orient_matrix_ub_23 0.420527E-1 _diffrn_orient_matrix_ub_31 0.740242E-1 _diffrn_orient_matrix_ub_32 -0.120705 _diffrn_orient_matrix_ub_33 0.33166E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_av_R_equivalents 0.034 _diffrn_reflns_av_unetI/netI ? _diffrn_reflns_number 30041 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 27.4 _diffrn_reflns_theta_full 27.4 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 4605 _reflns_number_gt 3499 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ;For the methyl group, the hydrogen atoms were added at calculated positions using a riding model with U(H) = 1.5 * Ueq(bonded carbon atom). The torsion angle, which defines the orientation of the methyl group about the C-O bond, was refined. The rest of the hydrogen atoms were included in the model at calculated positions using a riding model with U(H) = 1.2 * Ueq(bonded atom). 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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0629P)^2^+0.2108P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4605 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0613 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1171 _refine_ls_wR_factor_gt 0.1054 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.259 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.046 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 C 0.16601(18) 0.82866(17) 0.36592(9) 0.0222(3) Uani 1 1 d . . . H1 H 0.06 0.9346 0.3726 0.027 Uiso 1 1 calc R . . C2 C 0.17728(19) 0.74656(17) 0.28136(9) 0.0243(3) Uani 1 1 d . . . H2A H 0.2729 0.6354 0.2793 0.029 Uiso 1 1 calc R . . H2B H 0.0634 0.7322 0.2813 0.029 Uiso 1 1 calc R . . C3 C 0.21503(18) 0.84723(16) 0.20008(9) 0.0223(3) Uani 1 1 d . . . C4 C 0.35894(18) 0.91873(16) 0.20510(8) 0.0216(3) Uani 1 1 d . . . H4 H 0.3368 1.0152 0.1627 0.026 Uiso 1 1 calc R . . C5 C 0.15667(18) 0.71714(16) 0.44529(8) 0.0217(3) Uani 1 1 d . . . C6 C 0.29330(19) 0.56364(17) 0.45162(9) 0.0261(3) Uani 1 1 d . . . H6 H 0.3954 0.5323 0.4073 0.031 Uiso 1 1 calc R . . C7 C 0.2815(2) 0.45680(18) 0.52173(10) 0.0294(3) Uani 1 1 d . . . H7 H 0.3758 0.3528 0.5256 0.035 Uiso 1 1 calc R . . C8 C 0.1330(2) 0.50072(18) 0.58628(9) 0.0286(3) Uani 1 1 d . . . H8 H 0.1237 0.4256 0.6336 0.034 Uiso 1 1 calc R . . C9 C -0.0018(2) 0.65365(19) 0.58218(9) 0.0305(3) Uani 1 1 d . . . H9 H -0.1029 0.6848 0.6272 0.037 Uiso 1 1 calc R . . C10 C 0.01060(19) 0.76226(18) 0.51185(9) 0.0267(3) Uani 1 1 d . . . H10 H -0.0816 0.868 0.5094 0.032 Uiso 1 1 calc R . . C11 C 0.54872(18) 0.80197(17) 0.17444(9) 0.0229(3) Uani 1 1 d . . . C12 C 0.6350(2) 0.83763(19) 0.09327(9) 0.0299(3) Uani 1 1 d . . . H12 H 0.5744 0.9332 0.0604 0.036 Uiso 1 1 calc R . . C13 C 0.8067(2) 0.7367(2) 0.05971(10) 0.0356(4) Uani 1 1 d . . . H13 H 0.8628 0.7632 0.0043 0.043 Uiso 1 1 calc R . . C14 C 0.8967(2) 0.5976(2) 0.10664(10) 0.0331(3) Uani 1 1 d . . . H14 H 1.0144 0.5275 0.0836 0.04 Uiso 1 1 calc R . . C15 C 0.8140(2) 0.56117(18) 0.18754(10) 0.0297(3) Uani 1 1 d . . . H15 H 0.8757 0.4656 0.22 0.036 Uiso 1 1 calc R . . C16 C 0.64181(19) 0.66268(17) 0.22185(9) 0.0258(3) Uani 1 1 d . . . H16 H 0.5874 0.637 0.2778 0.031 Uiso 1 1 calc R . . C17 C 0.43406(17) 1.07094(16) 0.30631(9) 0.0216(3) Uani 1 1 d . . . C18 C 0.44106(19) 1.20288(16) 0.24964(9) 0.0249(3) Uani 1 1 d . . . H18 H 0.372 1.2351 0.2036 0.03 Uiso 1 1 calc R . . C19 C 0.5487(2) 1.28699(17) 0.26043(9) 0.0276(3) Uani 1 1 d . . . H19 H 0.5553 1.375 0.2208 0.033 Uiso 1 1 calc R . . C20 C 0.64689(19) 1.24377(17) 0.32862(10) 0.0290(3) Uani 1 1 d . . . H20 H 0.7213 1.301 0.3356 0.035 Uiso 1 1 calc R . . C21 C 0.6353(2) 1.11636(18) 0.38636(10) 0.0296(3) Uani 1 1 d . . . H21 H 0.6996 1.0885 0.4342 0.036 Uiso 1 1 calc R . . C22 C 0.53069(19) 1.02844(17) 0.37538(9) 0.0261(3) Uani 1 1 d . . . H22 H 0.5253 0.9399 0.4148 0.031 Uiso 1 1 calc R . . C23 C 0.26730(18) 0.74226(17) 0.11781(9) 0.0233(3) Uani 1 1 d . . . C24 C 0.3035(2) 0.7515(2) -0.03625(10) 0.0367(4) Uani 1 1 d . . . H24A H 0.4304 0.6815 -0.0429 0.055 Uiso 1 1 calc R . . H24B H 0.2824 0.8319 -0.0854 0.055 Uiso 1 1 calc R . . H24C H 0.2332 0.6824 -0.0357 0.055 Uiso 1 1 calc R . . N1 N 0.31889(15) 0.98993(13) 0.29298(7) 0.0216(2) Uani 1 1 d . . . N2 N 0.03848(16) 0.99192(15) 0.18656(8) 0.0270(3) Uani 1 1 d . . . O1 O 0.32766(12) 0.86158(11) 0.36000(6) 0.0217(2) Uani 1 1 d . . . O2 O 0.03794(15) 1.13154(13) 0.16984(7) 0.0369(3) Uani 1 1 d . . . O3 O -0.09101(14) 0.95346(13) 0.19108(8) 0.0370(3) Uani 1 1 d . . . O4 O 0.31870(14) 0.59463(12) 0.11993(7) 0.0312(3) Uani 1 1 d . . . O5 O 0.25075(14) 0.83886(12) 0.04578(6) 0.0292(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0207(7) 0.0224(7) 0.0237(7) 0.0004(5) -0.0036(5) -0.0085(5) C2 0.0278(7) 0.0271(7) 0.0217(7) 0.0013(6) -0.0051(6) -0.0142(6) C3 0.0233(7) 0.0210(7) 0.0218(7) 0.0001(5) -0.0057(5) -0.0066(6) C4 0.0265(7) 0.0221(7) 0.0174(6) 0.0010(5) -0.0041(5) -0.0105(6) C5 0.0239(7) 0.0245(7) 0.0203(7) -0.0014(5) -0.0040(5) -0.0126(6) C6 0.0259(7) 0.0258(7) 0.0246(7) -0.0007(6) 0.0004(6) -0.0094(6) C7 0.0334(8) 0.0245(7) 0.0304(8) 0.0020(6) -0.0075(6) -0.0105(6) C8 0.0378(8) 0.0339(8) 0.0216(7) 0.0052(6) -0.0077(6) -0.0217(7) C9 0.0300(8) 0.0426(9) 0.0216(7) -0.0023(6) 0.0004(6) -0.0181(7) C10 0.0246(7) 0.0288(7) 0.0256(7) -0.0024(6) -0.0031(6) -0.0088(6) C11 0.0272(7) 0.0255(7) 0.0206(7) -0.0018(5) -0.0043(6) -0.0143(6) C12 0.0320(8) 0.0326(8) 0.0249(7) 0.0030(6) -0.0048(6) -0.0124(7) C13 0.0344(9) 0.0464(9) 0.0261(8) -0.0007(7) 0.0027(6) -0.0185(7) C14 0.0282(8) 0.0380(8) 0.0320(8) -0.0099(7) 0.0005(6) -0.0113(7) C15 0.0317(8) 0.0258(7) 0.0305(8) -0.0022(6) -0.0055(6) -0.0087(6) C16 0.0292(8) 0.0244(7) 0.0238(7) 0.0000(6) -0.0025(6) -0.0108(6) C17 0.0216(7) 0.0204(6) 0.0221(7) -0.0040(5) 0.0001(5) -0.0076(5) C18 0.0303(8) 0.0224(7) 0.0222(7) -0.0008(5) -0.0038(6) -0.0100(6) C19 0.0330(8) 0.0226(7) 0.0269(7) -0.0026(6) 0.0020(6) -0.0126(6) C20 0.0274(8) 0.0277(7) 0.0349(8) -0.0078(6) -0.0009(6) -0.0138(6) C21 0.0295(8) 0.0292(8) 0.0316(8) -0.0027(6) -0.0101(6) -0.0096(6) C22 0.0299(8) 0.0228(7) 0.0263(7) 0.0021(6) -0.0062(6) -0.0103(6) C23 0.0234(7) 0.0259(7) 0.0216(7) -0.0006(5) -0.0053(5) -0.0094(6) C24 0.0462(10) 0.0409(9) 0.0207(7) -0.0055(6) -0.0044(7) -0.0129(8) N1 0.0289(6) 0.0198(6) 0.0178(5) 0.0025(4) -0.0039(5) -0.0114(5) N2 0.0270(7) 0.0275(6) 0.0246(6) -0.0025(5) -0.0057(5) -0.0067(5) O1 0.0260(5) 0.0230(5) 0.0187(5) 0.0044(4) -0.0046(4) -0.0126(4) O2 0.0376(6) 0.0244(5) 0.0456(7) 0.0047(5) -0.0124(5) -0.0066(5) O3 0.0250(6) 0.0389(6) 0.0486(7) -0.0046(5) -0.0099(5) -0.0110(5) O4 0.0398(6) 0.0246(5) 0.0285(5) -0.0029(4) -0.0068(5) -0.0100(5) O5 0.0373(6) 0.0289(5) 0.0194(5) 0.0001(4) -0.0057(4) -0.0096(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.4469(15) . ? C1 C5 1.5065(18) . ? C1 C2 1.5272(18) . ? C1 H1 1 . ? C2 C3 1.5219(18) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C23 1.5429(19) . ? C3 C4 1.5479(18) . ? C3 N2 1.5549(17) . ? C4 N1 1.4830(16) . ? C4 C11 1.520(2) . ? C4 H4 1 . ? C5 C10 1.3878(19) . ? C5 C6 1.394(2) . ? C6 C7 1.3798(19) . ? C6 H6 0.95 . ? C7 C8 1.382(2) . ? C7 H7 0.95 . ? C8 C9 1.380(2) . ? C8 H8 0.95 . ? C9 C10 1.393(2) . ? C9 H9 0.95 . ? C10 H10 0.95 . ? C11 C16 1.3930(19) . ? C11 C12 1.3976(19) . ? C12 C13 1.383(2) . ? C12 H12 0.95 . ? C13 C14 1.380(2) . ? C13 H13 0.95 . ? C14 C15 1.384(2) . ? C14 H14 0.95 . ? C15 C16 1.390(2) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C17 C22 1.3905(19) . ? C17 C18 1.3953(18) . ? C17 N1 1.4304(17) . ? C18 C19 1.3858(19) . ? C18 H18 0.95 . ? C19 C20 1.387(2) . ? C19 H19 0.95 . ? C20 C21 1.383(2) . ? C20 H20 0.95 . ? C21 C22 1.3913(19) . ? C21 H21 0.95 . ? C22 H22 0.95 . ? C23 O4 1.1949(16) . ? C23 O5 1.3317(16) . ? C24 O5 1.4575(17) . ? C24 H24A 0.98 . ? C24 H24B 0.98 . ? C24 H24C 0.98 . ? N1 O1 1.4464(13) . ? N2 O3 1.2197(15) . ? N2 O2 1.2215(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 O1 C1 C5 107.34(10) . . ? O1 C1 C2 107.53(10) . . ? C5 C1 C2 112.06(11) . . ? O1 C1 H1 109.9 . . ? C5 C1 H1 109.9 . . ? C2 C1 H1 109.9 . . ? C3 C2 C1 112.32(11) . . ? C3 C2 H2A 109.1 . . ? C1 C2 H2A 109.1 . . ? C3 C2 H2B 109.1 . . ? C1 C2 H2B 109.1 . . ? H2A C2 H2B 107.9 . . ? C2 C3 C23 110.06(11) . . ? C2 C3 C4 113.70(10) . . ? C23 C3 C4 110.30(11) . . ? C2 C3 N2 108.46(11) . . ? C23 C3 N2 104.84(10) . . ? C4 C3 N2 109.09(10) . . ? N1 C4 C11 117.55(11) . . ? N1 C4 C3 107.35(10) . . ? C11 C4 C3 114.15(11) . . ? N1 C4 H4 105.6 . . ? C11 C4 H4 105.6 . . ? C3 C4 H4 105.6 . . ? C10 C5 C6 118.79(12) . . ? C10 C5 C1 121.04(12) . . ? C6 C5 C1 120.14(12) . . ? C7 C6 C5 120.60(13) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C8 120.16(14) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C9 C8 C7 120.08(13) . . ? C9 C8 H8 120 . . ? C7 C8 H8 120 . . ? C8 C9 C10 119.80(14) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C5 C10 C9 120.51(13) . . ? C5 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C16 C11 C12 118.10(13) . . ? C16 C11 C4 124.40(12) . . ? C12 C11 C4 117.50(12) . . ? C13 C12 C11 121.38(14) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C14 C13 C12 120.02(14) . . ? C14 C13 H13 120 . . ? C12 C13 H13 120 . . ? C13 C14 C15 119.40(15) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C14 C15 C16 120.84(14) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C15 C16 C11 120.24(13) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? C22 C17 C18 119.57(12) . . ? C22 C17 N1 122.59(12) . . ? C18 C17 N1 117.76(12) . . ? C19 C18 C17 120.06(13) . . ? C19 C18 H18 120 . . ? C17 C18 H18 120 . . ? C18 C19 C20 120.52(13) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C21 C20 C19 119.28(13) . . ? C21 C20 H20 120.4 . . ? C19 C20 H20 120.4 . . ? C20 C21 C22 120.90(13) . . ? C20 C21 H21 119.5 . . ? C22 C21 H21 119.5 . . ? C17 C22 C21 119.62(13) . . ? C17 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? O4 C23 O5 125.77(13) . . ? O4 C23 C3 123.69(12) . . ? O5 C23 C3 110.53(11) . . ? O5 C24 H24A 109.5 . . ? O5 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O5 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C17 N1 O1 108.63(9) . . ? C17 N1 C4 114.37(10) . . ? O1 N1 C4 109.84(9) . . ? O3 N2 O2 124.66(12) . . ? O3 N2 C3 115.45(11) . . ? O2 N2 C3 119.84(11) . . ? N1 O1 C1 106.32(9) . . ? C23 O5 C24 115.07(11) . . ? 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 O1 C1 C2 C3 -53.58(14) . . . . ? C5 C1 C2 C3 -171.30(11) . . . . ? C1 C2 C3 C23 167.13(11) . . . . ? C1 C2 C3 C4 42.83(16) . . . . ? C1 C2 C3 N2 -78.70(13) . . . . ? C2 C3 C4 N1 -45.13(14) . . . . ? C23 C3 C4 N1 -169.31(10) . . . . ? N2 C3 C4 N1 76.04(12) . . . . ? C2 C3 C4 C11 87.02(14) . . . . ? C23 C3 C4 C11 -37.16(14) . . . . ? N2 C3 C4 C11 -151.81(11) . . . . ? O1 C1 C5 C10 123.26(13) . . . . ? C2 C1 C5 C10 -118.90(14) . . . . ? O1 C1 C5 C6 -58.75(15) . . . . ? C2 C1 C5 C6 59.08(16) . . . . ? C10 C5 C6 C7 1.6(2) . . . . ? C1 C5 C6 C7 -176.47(12) . . . . ? C5 C6 C7 C8 0.4(2) . . . . ? C6 C7 C8 C9 -1.9(2) . . . . ? C7 C8 C9 C10 1.3(2) . . . . ? C6 C5 C10 C9 -2.2(2) . . . . ? C1 C5 C10 C9 175.85(12) . . . . ? C8 C9 C10 C5 0.8(2) . . . . ? N1 C4 C11 C16 53.37(18) . . . . ? C3 C4 C11 C16 -73.68(16) . . . . ? N1 C4 C11 C12 -126.50(13) . . . . ? C3 C4 C11 C12 106.45(14) . . . . ? C16 C11 C12 C13 1.1(2) . . . . ? C4 C11 C12 C13 -179.05(13) . . . . ? C11 C12 C13 C14 -0.1(2) . . . . ? C12 C13 C14 C15 -0.5(2) . . . . ? C13 C14 C15 C16 0.1(2) . . . . ? C14 C15 C16 C11 0.9(2) . . . . ? C12 C11 C16 C15 -1.5(2) . . . . ? C4 C11 C16 C15 178.66(12) . . . . ? C22 C17 C18 C19 2.3(2) . . . . ? N1 C17 C18 C19 179.15(12) . . . . ? C17 C18 C19 C20 -1.6(2) . . . . ? C18 C19 C20 C21 -0.5(2) . . . . ? C19 C20 C21 C22 1.8(2) . . . . ? C18 C17 C22 C21 -1.0(2) . . . . ? N1 C17 C22 C21 -177.67(13) . . . . ? C20 C21 C22 C17 -1.1(2) . . . . ? C2 C3 C23 O4 -19.30(18) . . . . ? C4 C3 C23 O4 106.94(15) . . . . ? N2 C3 C23 O4 -135.75(13) . . . . ? C2 C3 C23 O5 162.13(11) . . . . ? C4 C3 C23 O5 -71.62(13) . . . . ? N2 C3 C23 O5 45.68(14) . . . . ? C22 C17 N1 O1 -1.44(17) . . . . ? C18 C17 N1 O1 -178.20(11) . . . . ? C22 C17 N1 C4 -124.54(14) . . . . ? C18 C17 N1 C4 58.71(16) . . . . ? C11 C4 N1 C17 53.46(15) . . . . ? C3 C4 N1 C17 -176.26(10) . . . . ? C11 C4 N1 O1 -68.98(13) . . . . ? C3 C4 N1 O1 61.30(12) . . . . ? C2 C3 N2 O3 -48.01(15) . . . . ? C23 C3 N2 O3 69.54(14) . . . . ? C4 C3 N2 O3 -172.33(11) . . . . ? C2 C3 N2 O2 134.25(13) . . . . ? C23 C3 N2 O2 -108.19(13) . . . . ? C4 C3 N2 O2 9.93(16) . . . . ? C17 N1 O1 C1 158.24(10) . . . . ? C4 N1 O1 C1 -75.98(12) . . . . ? C5 C1 O1 N1 -170.53(10) . . . . ? C2 C1 O1 N1 68.74(12) . . . . ? O4 C23 O5 C24 -0.8(2) . . . . ? C3 C23 O5 C24 177.74(11) . . . . ? # END of CIF _database_code_depnum_ccdc_archive 'CCDC 936757' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Mattson1932 _audit_creation_date 2013-02-18T11:33:30-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 'Mattson 1932' _chemical_formula_moiety 'C22 H20 N2 O3' _chemical_formula_sum 'C22 H20 N2 O3' _chemical_formula_weight 360.4 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M ' P 1' _symmetry_space_group_name_Hall 'P 1' _symmetry_Int_Tables_number 1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 7.3566(2) _cell_length_b 8.0059(2) _cell_length_c 9.0060(2) _cell_angle_alpha 65.624(1) _cell_angle_beta 71.772(2) _cell_angle_gamma 81.292(2) _cell_volume 458.74(2) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2089 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 190 _exptl_special_details ;All work was done at 150 K using an Oxford Cryosystems Cryostream Cooler. The data collection strategy was set up to measure a hemisphere of reciprocal space with a redundancy factor of 3.7, which means that 90% of these reflections were measured at least 3.7 times. Phi and omega scans with a frame width of 2.0 degrees were used. Data integration was done with Denzo, and scaling and merging of the data was done with Scalepack. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.877 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.13809E-1 _diffrn_orient_matrix_ub_12 0.133704 _diffrn_orient_matrix_ub_13 -0.219933E-1 _diffrn_orient_matrix_ub_21 -0.138126 _diffrn_orient_matrix_ub_22 -0.162905E-1 _diffrn_orient_matrix_ub_23 0.657133E-1 _diffrn_orient_matrix_ub_31 0.350096E-1 _diffrn_orient_matrix_ub_32 -0.259942E-1 _diffrn_orient_matrix_ub_33 0.106317 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_av_R_equivalents 0.027 _diffrn_reflns_av_unetI/netI ? _diffrn_reflns_number 14559 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 27.45 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 4070 _reflns_number_gt 3724 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ;As the molecule crystallized in space group P1 with Z=1, the crystal contains one enantiomer, but the absolute configuration has not been determined by this set of X-ray data. The hydrogen atoms are included in the model at calculated positions using a riding model with U(H) = 1.2*Ueq(bonded atom). 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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0426P)^2^+0.0690P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4070 _refine_ls_number_parameters 244 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.0863 _refine_ls_wR_factor_gt 0.0824 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_diff_density_max 0.128 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.036 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 C 0.0611(2) 0.28199(19) 0.22883(18) 0.0237(3) Uani 1 1 d . . . H1 H 0.027 0.2835 0.3448 0.028 Uiso 1 1 calc R . . C2 C -0.1096(2) 0.3505(2) 0.15468(19) 0.0264(3) Uani 1 1 d . . . H2A H -0.1579 0.469 0.1644 0.032 Uiso 1 1 calc R . . H2B H -0.0668 0.3722 0.0326 0.032 Uiso 1 1 calc R . . C3 C -0.2709(2) 0.2151(2) 0.24420(19) 0.0257(3) Uani 1 1 d . . . H3 H -0.3627 0.2519 0.1737 0.031 Uiso 1 1 calc R . . C4 C -0.1985(2) 0.0173(2) 0.26760(18) 0.0242(3) Uani 1 1 d . . . H4 H -0.3056 -0.0665 0.3488 0.029 Uiso 1 1 calc R . . C5 C 0.2380(2) 0.3917(2) 0.11746(18) 0.0247(3) Uani 1 1 d . . . C6 C 0.3402(2) 0.3723(2) -0.03386(19) 0.0297(3) Uani 1 1 d . . . H6 H 0.2976 0.2902 -0.0671 0.036 Uiso 1 1 calc R . . C7 C 0.5037(2) 0.4722(2) -0.1361(2) 0.0325(4) Uani 1 1 d . . . H7 H 0.5738 0.4566 -0.238 0.039 Uiso 1 1 calc R . . C8 C 0.5650(2) 0.5942(2) -0.0905(2) 0.0329(4) Uani 1 1 d . . . H8 H 0.6763 0.6633 -0.1613 0.039 Uiso 1 1 calc R . . C9 C 0.4636(2) 0.6152(2) 0.0589(2) 0.0335(4) Uani 1 1 d . . . H9 H 0.5051 0.6993 0.0906 0.04 Uiso 1 1 calc R . . C10 C 0.3011(2) 0.5135(2) 0.1627(2) 0.0286(3) Uani 1 1 d . . . H10 H 0.2329 0.5276 0.2656 0.034 Uiso 1 1 calc R . . C11 C -0.1473(2) -0.00869(19) 0.09966(18) 0.0251(3) Uani 1 1 d . . . C12 C -0.2917(2) 0.0229(2) 0.0202(2) 0.0322(4) Uani 1 1 d . . . H12 H -0.4174 0.0559 0.0724 0.039 Uiso 1 1 calc R . . C13 C -0.2533(3) 0.0064(2) -0.1344(2) 0.0390(4) Uani 1 1 d . . . H13 H -0.3516 0.0315 -0.189 0.047 Uiso 1 1 calc R . . C14 C -0.0725(3) -0.0463(2) -0.2085(2) 0.0427(5) Uani 1 1 d . . . H14 H -0.0461 -0.0571 -0.3145 0.051 Uiso 1 1 calc R . . C15 C 0.0704(3) -0.0836(3) -0.1287(2) 0.0400(4) Uani 1 1 d . . . H15 H 0.1942 -0.1225 -0.1789 0.048 Uiso 1 1 calc R . . C16 C 0.0337(2) -0.0644(2) 0.0247(2) 0.0323(4) Uani 1 1 d . . . H16 H 0.1328 -0.0895 0.0785 0.039 Uiso 1 1 calc R . . C17 C 0.0236(2) -0.1998(2) 0.42650(18) 0.0243(3) Uani 1 1 d . . . C18 C -0.0903(2) -0.3514(2) 0.4866(2) 0.0287(3) Uani 1 1 d . . . H18 H -0.2118 -0.3358 0.4657 0.034 Uiso 1 1 calc R . . C19 C -0.0257(2) -0.5254(2) 0.5773(2) 0.0339(4) Uani 1 1 d . . . H19 H -0.1052 -0.6275 0.6201 0.041 Uiso 1 1 calc R . . C20 C 0.1518(3) -0.5518(2) 0.6059(2) 0.0378(4) Uani 1 1 d . . . H20 H 0.1951 -0.6711 0.6676 0.045 Uiso 1 1 calc R . . C21 C 0.2660(3) -0.4022(3) 0.5433(2) 0.0400(4) Uani 1 1 d . . . H21 H 0.3895 -0.4197 0.5607 0.048 Uiso 1 1 calc R . . C22 C 0.2034(2) -0.2268(2) 0.4556(2) 0.0323(4) Uani 1 1 d . . . H22 H 0.2828 -0.1251 0.4154 0.039 Uiso 1 1 calc R . . N1 N -0.04666(16) -0.01879(16) 0.35074(15) 0.0230(3) Uani 1 1 d . . . N2 N -0.37960(19) 0.2145(2) 0.41927(18) 0.0331(3) Uani 1 1 d . . . O1 O 0.11236(14) 0.09751(13) 0.23739(12) 0.0248(2) Uani 1 1 d . . . O2 O -0.5011(2) 0.0982(2) 0.50943(18) 0.0542(4) Uani 1 1 d . . . O3 O -0.34535(17) 0.33071(19) 0.46079(17) 0.0425(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0232(7) 0.0228(7) 0.0258(7) -0.0112(6) -0.0055(6) 0.0000(6) C2 0.0242(7) 0.0248(7) 0.0300(8) -0.0110(6) -0.0075(6) 0.0010(6) C3 0.0224(7) 0.0275(7) 0.0269(7) -0.0121(6) -0.0057(6) 0.0027(6) C4 0.0215(7) 0.0241(7) 0.0251(7) -0.0086(6) -0.0051(6) -0.0009(6) C5 0.0244(7) 0.0232(7) 0.0238(7) -0.0064(6) -0.0077(6) 0.0016(6) C6 0.0299(8) 0.0343(8) 0.0259(8) -0.0121(7) -0.0074(6) -0.0036(7) C7 0.0285(8) 0.0394(9) 0.0238(8) -0.0088(7) -0.0038(6) -0.0024(7) C8 0.0267(8) 0.0294(8) 0.0341(9) -0.0048(7) -0.0064(6) -0.0039(6) C9 0.0322(8) 0.0277(8) 0.0406(9) -0.0128(7) -0.0090(7) -0.0046(7) C10 0.0275(8) 0.0261(7) 0.0311(8) -0.0123(6) -0.0054(6) -0.0001(6) C11 0.0312(7) 0.0200(7) 0.0237(7) -0.0078(6) -0.0069(6) -0.0033(6) C12 0.0357(9) 0.0274(8) 0.0362(9) -0.0110(7) -0.0147(7) -0.0022(6) C13 0.0577(11) 0.0300(8) 0.0352(9) -0.0085(7) -0.0228(8) -0.0084(8) C14 0.0703(13) 0.0334(9) 0.0287(8) -0.0151(7) -0.0118(9) -0.0088(9) C15 0.0489(10) 0.0379(9) 0.0326(9) -0.0192(8) -0.0023(8) -0.0020(8) C16 0.0348(9) 0.0319(8) 0.0303(8) -0.0136(7) -0.0076(7) 0.0005(7) C17 0.0264(7) 0.0246(7) 0.0206(7) -0.0096(6) -0.0050(6) 0.0026(6) C18 0.0263(8) 0.0273(8) 0.0269(7) -0.0088(6) -0.0025(6) -0.0007(6) C19 0.0403(10) 0.0254(8) 0.0279(8) -0.0090(6) -0.0003(7) -0.0017(7) C20 0.0511(11) 0.0271(9) 0.0319(9) -0.0069(7) -0.0173(8) 0.0078(8) C21 0.0409(10) 0.0379(9) 0.0445(10) -0.0136(8) -0.0242(8) 0.0089(8) C22 0.0356(9) 0.0289(8) 0.0364(9) -0.0127(7) -0.0166(7) 0.0018(7) N1 0.0200(6) 0.0208(6) 0.0245(6) -0.0063(5) -0.0041(5) -0.0019(5) N2 0.0244(7) 0.0391(8) 0.0361(8) -0.0190(7) -0.0054(6) 0.0052(6) O1 0.0212(5) 0.0214(5) 0.0280(5) -0.0078(4) -0.0039(4) -0.0011(4) O2 0.0464(8) 0.0519(9) 0.0510(8) -0.0251(7) 0.0177(7) -0.0156(7) O3 0.0344(7) 0.0542(8) 0.0499(7) -0.0357(7) -0.0069(6) 0.0027(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.4440(17) . ? C1 C5 1.508(2) . ? C1 C2 1.529(2) . ? C1 H1 1 . ? C2 C3 1.517(2) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 N2 1.527(2) . ? C3 C4 1.542(2) . ? C3 H3 1 . ? C4 N1 1.4627(19) . ? C4 C11 1.534(2) . ? C4 H4 1 . ? C5 C10 1.384(2) . ? C5 C6 1.395(2) . ? C6 C7 1.387(2) . ? C6 H6 0.95 . ? C7 C8 1.381(2) . ? C7 H7 0.95 . ? C8 C9 1.385(2) . ? C8 H8 0.95 . ? C9 C10 1.390(2) . ? C9 H9 0.95 . ? C10 H10 0.95 . ? C11 C16 1.391(2) . ? C11 C12 1.396(2) . ? C12 C13 1.390(2) . ? C12 H12 0.95 . ? C13 C14 1.378(3) . ? C13 H13 0.95 . ? C14 C15 1.383(3) . ? C14 H14 0.95 . ? C15 C16 1.391(2) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C17 C22 1.396(2) . ? C17 C18 1.397(2) . ? C17 N1 1.4180(18) . ? C18 C19 1.391(2) . ? C18 H18 0.95 . ? C19 C20 1.378(3) . ? C19 H19 0.95 . ? C20 C21 1.382(3) . ? C20 H20 0.95 . ? C21 C22 1.387(2) . ? C21 H21 0.95 . ? C22 H22 0.95 . ? N1 O1 1.4407(15) . ? N2 O3 1.2187(18) . ? N2 O2 1.2247(19) . ? 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 O1 C1 C5 105.23(11) . . ? O1 C1 C2 108.70(11) . . ? C5 C1 C2 112.67(12) . . ? O1 C1 H1 110 . . ? C5 C1 H1 110 . . ? C2 C1 H1 110 . . ? C3 C2 C1 112.20(12) . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2B 109.2 . . ? C1 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C2 C3 N2 111.89(12) . . ? C2 C3 C4 112.29(12) . . ? N2 C3 C4 107.71(12) . . ? C2 C3 H3 108.3 . . ? N2 C3 H3 108.3 . . ? C4 C3 H3 108.3 . . ? N1 C4 C11 117.27(12) . . ? N1 C4 C3 105.49(11) . . ? C11 C4 C3 111.01(12) . . ? N1 C4 H4 107.6 . . ? C11 C4 H4 107.6 . . ? C3 C4 H4 107.6 . . ? C10 C5 C6 118.96(14) . . ? C10 C5 C1 120.84(13) . . ? C6 C5 C1 120.20(13) . . ? C7 C6 C5 120.35(15) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C8 C7 C6 120.32(15) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C9 119.68(15) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C8 C9 C10 120.09(15) . . ? C8 C9 H9 120 . . ? C10 C9 H9 120 . . ? C5 C10 C9 120.59(15) . . ? C5 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C16 C11 C12 118.75(14) . . ? C16 C11 C4 123.44(13) . . ? C12 C11 C4 117.81(13) . . ? C13 C12 C11 120.60(16) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C14 C13 C12 119.98(17) . . ? C14 C13 H13 120 . . ? C12 C13 H13 120 . . ? C13 C14 C15 120.05(16) . . ? C13 C14 H14 120 . . ? C15 C14 H14 120 . . ? C14 C15 C16 120.23(17) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C11 120.33(16) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? C22 C17 C18 118.97(14) . . ? C22 C17 N1 119.52(13) . . ? C18 C17 N1 121.25(13) . . ? C19 C18 C17 119.94(14) . . ? C19 C18 H18 120 . . ? C17 C18 H18 120 . . ? C20 C19 C18 121.02(15) . . ? C20 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C19 C20 C21 118.97(15) . . ? C19 C20 H20 120.5 . . ? C21 C20 H20 120.5 . . ? C20 C21 C22 121.16(17) . . ? C20 C21 H21 119.4 . . ? C22 C21 H21 119.4 . . ? C21 C22 C17 119.91(15) . . ? C21 C22 H22 120 . . ? C17 C22 H22 120 . . ? C17 N1 O1 109.07(10) . . ? C17 N1 C4 121.03(12) . . ? O1 N1 C4 109.59(10) . . ? O3 N2 O2 123.41(14) . . ? O3 N2 C3 119.13(13) . . ? O2 N2 C3 117.43(13) . . ? N1 O1 C1 108.53(9) . . ? 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 O1 C1 C2 C3 50.39(15) . . . . ? C5 C1 C2 C3 166.62(12) . . . . ? C1 C2 C3 N2 74.40(15) . . . . ? C1 C2 C3 C4 -46.87(17) . . . . ? C2 C3 C4 N1 52.95(15) . . . . ? N2 C3 C4 N1 -70.68(14) . . . . ? C2 C3 C4 C11 -75.06(15) . . . . ? N2 C3 C4 C11 161.31(12) . . . . ? O1 C1 C5 C10 -134.99(13) . . . . ? C2 C1 C5 C10 106.73(15) . . . . ? O1 C1 C5 C6 45.35(16) . . . . ? C2 C1 C5 C6 -72.94(17) . . . . ? C10 C5 C6 C7 0.7(2) . . . . ? C1 C5 C6 C7 -179.61(15) . . . . ? C5 C6 C7 C8 -1.1(2) . . . . ? C6 C7 C8 C9 0.6(2) . . . . ? C7 C8 C9 C10 0.2(2) . . . . ? C6 C5 C10 C9 0.1(2) . . . . ? C1 C5 C10 C9 -179.53(14) . . . . ? C8 C9 C10 C5 -0.6(2) . . . . ? N1 C4 C11 C16 0.2(2) . . . . ? C3 C4 C11 C16 121.48(15) . . . . ? N1 C4 C11 C12 179.14(13) . . . . ? C3 C4 C11 C12 -59.54(17) . . . . ? C16 C11 C12 C13 -2.7(2) . . . . ? C4 C11 C12 C13 178.31(14) . . . . ? C11 C12 C13 C14 1.7(2) . . . . ? C12 C13 C14 C15 0.3(3) . . . . ? C13 C14 C15 C16 -1.4(3) . . . . ? C14 C15 C16 C11 0.4(3) . . . . ? C12 C11 C16 C15 1.6(2) . . . . ? C4 C11 C16 C15 -179.44(15) . . . . ? C22 C17 C18 C19 1.4(2) . . . . ? N1 C17 C18 C19 -172.77(13) . . . . ? C17 C18 C19 C20 -1.5(2) . . . . ? C18 C19 C20 C21 0.2(2) . . . . ? C19 C20 C21 C22 1.2(3) . . . . ? C20 C21 C22 C17 -1.2(3) . . . . ? C18 C17 C22 C21 -0.1(2) . . . . ? N1 C17 C22 C21 174.19(14) . . . . ? C22 C17 N1 O1 31.11(17) . . . . ? C18 C17 N1 O1 -154.73(13) . . . . ? C22 C17 N1 C4 159.58(13) . . . . ? C18 C17 N1 C4 -26.3(2) . . . . ? C11 C4 N1 C17 -70.21(17) . . . . ? C3 C4 N1 C17 165.64(12) . . . . ? C11 C4 N1 O1 58.03(15) . . . . ? C3 C4 N1 O1 -66.12(13) . . . . ? C2 C3 N2 O3 8.43(19) . . . . ? C4 C3 N2 O3 132.31(14) . . . . ? C2 C3 N2 O2 -173.27(14) . . . . ? C4 C3 N2 O2 -49.39(18) . . . . ? C17 N1 O1 C1 -151.21(11) . . . . ? C4 N1 O1 C1 74.19(13) . . . . ? C5 C1 O1 N1 176.52(10) . . . . ? C2 C1 O1 N1 -62.56(13) . . . . ? # END of CIF _database_code_depnum_ccdc_archive 'CCDC 941136' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Mattson1956 _audit_creation_date 2013-06-13T10:52:33-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 'Mattson 1956' _chemical_formula_moiety 'C24 H21 Cl1 N2 O5' _chemical_formula_sum 'C24 H21 Cl N2 O5' _chemical_formula_weight 452.88 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system orthorhombic _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' _space_group_IT_number 19 loop_ _space_group_symop_operation_xyz x,y,z 1/2-x,-y,1/2+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z _cell_length_a 8.57840(1) _cell_length_b 15.2797(2) _cell_length_c 16.5909(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2174.66(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2845 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description 'rectangular block' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_special_details ;All work was done at 150 K using an Oxford Cryosystems Cryostream Cooler. The data collection strategy was set up to measure an octant of reciprocal space with a redundancy factor of 4.3, which means that 90% of these reflections were measured at least 4.3 times. Phi and omega scans with a frame width of 1.0 degree were used. Data integration was done with Denzo, and scaling and merging of the data was done with Scalepack. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.834 _exptl_absorpt_correction_T_max 0.968 _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.436277E-1 _diffrn_orient_matrix_ub_12 -0.602394E-1 _diffrn_orient_matrix_ub_13 -0.67988E-2 _diffrn_orient_matrix_ub_21 -0.164175E-1 _diffrn_orient_matrix_ub_22 0.115607E-1 _diffrn_orient_matrix_ub_23 -0.587157E-1 _diffrn_orient_matrix_ub_31 0.106846 _diffrn_orient_matrix_ub_32 -0.228208E-1 _diffrn_orient_matrix_ub_33 -0.117981E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_theta_min 2.455 _diffrn_reflns_theta_max 27.474 _diffrn_reflns_theta_full 27.5 _diffrn_reflns_number 31966 _diffrn_reflns_av_R_equivalents 0.033 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_point_group_measured_fraction_ful 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.999 _reflns_number_total 4977 _reflns_number_gt 4358 _reflns_threshold_expression 'I > 2\s(I)' #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ;For the methyl group, the hydrogen atoms were added at calculated positions using a riding model with U(H) = 1.5 * Ueq(bonded carbon atom). The torsion angle, which defines the orientation of this methyl group about the O-C bond, was refined. The rest of the hydrogen atoms were included in the model at calculated positions using a riding model with U(H) = 1.2 * Ueq(bonded atom). ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0422P)^2^+0.3942P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4977 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0446 _refine_ls_R_factor_gt 0.035 _refine_ls_wR_factor_ref 0.0838 _refine_ls_wR_factor_gt 0.079 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details ; Flack x determined using 1714 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack -0.034(16) _refine_diff_density_max 0.159 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.039 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4455(3) 0.52758(14) 0.57257(12) 0.0262(4) Uani 1 d . . H1 H 0.3728 0.5029 0.5313 0.031 Uiso 1 calc . . C2 C 0.5420(3) 0.45405(14) 0.60971(13) 0.0270(5) Uani 1 d . . H2A H 0.6025 0.4239 0.5671 0.032 Uiso 1 calc . . H2B H 0.6163 0.4786 0.6494 0.032 Uiso 1 calc . . C3 C 0.4341(3) 0.38941(13) 0.65102(13) 0.0257(4) Uani 1 d . . C4 C 0.3226(3) 0.43488(13) 0.71150(13) 0.0246(4) Uani 1 d . . H4 H 0.2401 0.3908 0.7244 0.03 Uiso 1 calc . . C5 C 0.5479(2) 0.59557(14) 0.53426(13) 0.0267(4) Uani 1 d . . C6 C 0.6500(3) 0.64616(14) 0.58021(15) 0.0327(5) Uani 1 d . . H6 H 0.6501 0.6409 0.6373 0.039 Uiso 1 calc . . C7 C 0.7514(3) 0.70428(15) 0.54272(17) 0.0383(6) Uani 1 d . . H7 H 0.8209 0.7386 0.5742 0.046 Uiso 1 calc . . C8 C 0.7515(3) 0.71231(16) 0.45963(18) 0.0430(6) Uani 1 d . . H8 H 0.8211 0.752 0.4342 0.052 Uiso 1 calc . . C9 C 0.6510(3) 0.66284(17) 0.41392(16) 0.0420(6) Uani 1 d . . H9 H 0.6513 0.6684 0.3569 0.05 Uiso 1 calc . . C10 C 0.5493(3) 0.60488(15) 0.45086(14) 0.0331(5) Uani 1 d . . H10 H 0.4798 0.5712 0.4189 0.04 Uiso 1 calc . . C11 C 0.3341(3) 0.33514(14) 0.59122(14) 0.0294(5) Uani 1 d . . C12 C 0.3336(4) 0.2701(2) 0.46185(19) 0.0550(8) Uani 1 d . . H12A H 0.2799 0.2193 0.4849 0.082 Uiso 1 calc . . H12B H 0.4083 0.2504 0.421 0.082 Uiso 1 calc . . H12C H 0.257 0.3092 0.4368 0.082 Uiso 1 calc . . C13 C 0.3910(2) 0.46234(14) 0.79184(13) 0.0257(4) Uani 1 d . . C14 C 0.3754(3) 0.40419(16) 0.85640(15) 0.0340(5) Uani 1 d . . H14 H 0.3268 0.3491 0.8478 0.041 Uiso 1 calc . . C15 C 0.4292(3) 0.42526(16) 0.93276(14) 0.0374(6) Uani 1 d . . H15 H 0.4188 0.385 0.976 0.045 Uiso 1 calc . . C16 C 0.4983(3) 0.50604(16) 0.94486(13) 0.0302(5) Uani 1 d . . C17 C 0.5119(3) 0.56545(15) 0.88261(14) 0.0309(5) Uani 1 d . . H17 H 0.5573 0.6212 0.892 0.037 Uiso 1 calc . . C18 C 0.4588(3) 0.54334(15) 0.80590(13) 0.0282(5) Uani 1 d . . H18 H 0.469 0.584 0.7629 0.034 Uiso 1 calc . . C19 C 0.1226(2) 0.54862(14) 0.70569(12) 0.0248(4) Uani 1 d . . C20 C -0.0009(3) 0.49886(16) 0.73525(14) 0.0308(5) Uani 1 d . . H20 H -0.0007 0.4371 0.7283 0.037 Uiso 1 calc . . C21 C -0.1234(3) 0.53866(17) 0.77453(14) 0.0346(5) Uani 1 d . . H21 H -0.2069 0.5042 0.7947 0.042 Uiso 1 calc . . C22 C -0.1255(3) 0.62876(17) 0.78478(16) 0.0404(6) Uani 1 d . . H22 H -0.2102 0.6563 0.8115 0.048 Uiso 1 calc . . C23 C -0.0031(3) 0.67773(17) 0.75570(18) 0.0444(7) Uani 1 d . . H23 H -0.0041 0.7394 0.7628 0.053 Uiso 1 calc . . C24 C 0.1220(3) 0.63873(16) 0.71613(15) 0.0365(6) Uani 1 d . . H24 H 0.2059 0.6733 0.6966 0.044 Uiso 1 calc . . Cl Cl 0.56978(7) 0.53235(5) 1.03935(4) 0.04298(17) Uani 1 d . . N1 N 0.2443(2) 0.50401(12) 0.66350(11) 0.0246(4) Uani 1 d . . N2 N 0.5301(2) 0.32137(12) 0.69794(12) 0.0305(4) Uani 1 d . . O1 O 0.35727(17) 0.56825(9) 0.63616(9) 0.0259(3) Uani 1 d . . O2 O 0.2029(2) 0.31249(11) 0.60366(11) 0.0412(4) Uani 1 d . . O3 O 0.4164(2) 0.31708(12) 0.52571(10) 0.0415(4) Uani 1 d . . O4 O 0.6687(2) 0.33411(12) 0.70757(13) 0.0494(5) Uani 1 d . . O5 O 0.4593(2) 0.25845(10) 0.72435(12) 0.0429(4) Uani 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0258(11) 0.0264(11) 0.0264(10) -0.0030(8) 0.0055(9) -0.0018(9) C2 0.0246(11) 0.0221(10) 0.0344(11) -0.0005(9) 0.0062(9) -0.0011(9) C3 0.0228(10) 0.0214(10) 0.0330(11) 0.0010(8) 0.0025(9) 0.0011(9) C4 0.0212(11) 0.0217(10) 0.0309(11) 0.0022(8) 0.0030(9) 0.0002(8) C5 0.0255(11) 0.0232(10) 0.0314(11) 0.0011(9) 0.0071(10) 0.0030(9) C6 0.0361(13) 0.0282(12) 0.0339(12) -0.0021(9) 0.0058(10) -0.0031(10) C7 0.0346(13) 0.0269(12) 0.0532(15) -0.0049(11) 0.0080(12) -0.0046(10) C8 0.0433(15) 0.0298(13) 0.0560(16) 0.0079(12) 0.0177(14) -0.0030(11) C9 0.0489(16) 0.0399(14) 0.0373(13) 0.0084(11) 0.0100(12) -0.0019(13) C10 0.0346(13) 0.0338(12) 0.0308(12) 0.0036(10) 0.0038(10) -0.0019(10) C11 0.0304(12) 0.0221(10) 0.0357(12) -0.0006(9) 0.0013(10) 0.0014(10) C12 0.0557(18) 0.0628(19) 0.0464(16) -0.0213(15) -0.0074(15) -0.0035(15) C13 0.0211(10) 0.0255(10) 0.0305(11) 0.0024(9) 0.0037(8) 0.0038(9) C14 0.0356(13) 0.0292(11) 0.0372(12) 0.0054(10) 0.0009(10) -0.0026(10) C15 0.0405(14) 0.0380(13) 0.0337(12) 0.0116(10) 0.0015(11) 0.0009(12) C16 0.0223(11) 0.0411(13) 0.0272(11) 0.0012(10) 0.0006(8) 0.0052(10) C17 0.0282(12) 0.0325(12) 0.0321(12) -0.0004(9) 0.0041(9) -0.0031(9) C18 0.0283(11) 0.0288(11) 0.0276(11) 0.0036(9) 0.0034(9) -0.0007(9) C19 0.0229(10) 0.0284(11) 0.0230(10) 0.0007(8) 0.0005(8) 0.0043(9) C20 0.0280(12) 0.0296(11) 0.0349(12) 0.0007(9) 0.0021(10) 0.0023(10) C21 0.0259(12) 0.0422(13) 0.0358(12) 0.0041(11) 0.0067(9) 0.0025(10) C22 0.0332(13) 0.0437(14) 0.0442(15) -0.0006(12) 0.0123(11) 0.0105(11) C23 0.0418(15) 0.0308(13) 0.0606(17) -0.0021(12) 0.0111(13) 0.0084(11) C24 0.0354(14) 0.0301(12) 0.0439(14) 0.0015(10) 0.0087(11) 0.0027(10) Cl 0.0378(3) 0.0621(4) 0.0291(3) 0.0017(3) -0.0029(3) 0.0006(3) N1 0.0222(9) 0.0221(8) 0.0296(9) 0.0034(7) 0.0039(7) -0.0003(7) N2 0.0297(11) 0.0228(9) 0.0391(11) 0.0002(8) 0.0011(8) 0.0047(8) O1 0.0256(8) 0.0220(7) 0.0301(8) 0.0018(6) 0.0065(6) -0.0017(6) O2 0.0336(10) 0.0403(10) 0.0498(11) -0.0067(8) 0.0035(8) -0.0113(8) O3 0.0373(9) 0.0473(10) 0.0399(10) -0.0160(8) 0.0036(8) -0.0048(8) O4 0.0286(10) 0.0488(11) 0.0709(13) 0.0151(10) -0.0072(9) 0.0023(8) O5 0.0424(11) 0.0261(8) 0.0604(11) 0.0128(8) -0.0019(9) -0.0024(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.439(2) . ? C1 C5 1.502(3) . ? C1 C2 1.526(3) . ? C1 H1 1 . ? C2 C3 1.517(3) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 N2 1.538(3) . ? C3 C4 1.551(3) . ? C3 C11 1.552(3) . ? C4 N1 1.484(3) . ? C4 C13 1.516(3) . ? C4 H4 1 . ? C5 C10 1.391(3) . ? C5 C6 1.394(3) . ? C6 C7 1.390(3) . ? C6 H6 0.95 . ? C7 C8 1.384(4) . ? C7 H7 0.95 . ? C8 C9 1.375(4) . ? C8 H8 0.95 . ? C9 C10 1.386(3) . ? C9 H9 0.95 . ? C10 H10 0.95 . ? C11 O2 1.195(3) . ? C11 O3 1.325(3) . ? C12 O3 1.464(3) . ? C12 H12A 0.98 . ? C12 H12B 0.98 . ? C12 H12C 0.98 . ? C13 C18 1.387(3) . ? C13 C14 1.398(3) . ? C14 C15 1.386(3) . ? C14 H14 0.95 . ? C15 C16 1.384(3) . ? C15 H15 0.95 . ? C16 C17 1.380(3) . ? C16 Cl 1.731(2) . ? C17 C18 1.393(3) . ? C17 H17 0.95 . ? C18 H18 0.95 . ? C19 C24 1.388(3) . ? C19 C20 1.393(3) . ? C19 N1 1.430(3) . ? C20 C21 1.378(3) . ? C20 H20 0.95 . ? C21 C22 1.387(4) . ? C21 H21 0.95 . ? C22 C23 1.376(4) . ? C22 H22 0.95 . ? C23 C24 1.392(4) . ? C23 H23 0.95 . ? C24 H24 0.95 . ? N1 O1 1.452(2) . ? N2 O4 1.215(3) . ? N2 O5 1.219(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 O1 C1 C5 108.61(16) . . ? O1 C1 C2 107.90(16) . . ? C5 C1 C2 111.26(18) . . ? O1 C1 H1 109.7 . . ? C5 C1 H1 109.7 . . ? C2 C1 H1 109.7 . . ? C3 C2 C1 109.31(17) . . ? C3 C2 H2A 109.8 . . ? C1 C2 H2A 109.8 . . ? C3 C2 H2B 109.8 . . ? C1 C2 H2B 109.8 . . ? H2A C2 H2B 108.3 . . ? C2 C3 N2 109.99(17) . . ? C2 C3 C4 112.15(17) . . ? N2 C3 C4 107.80(17) . . ? C2 C3 C11 113.35(18) . . ? N2 C3 C11 104.98(16) . . ? C4 C3 C11 108.19(17) . . ? N1 C4 C13 116.77(17) . . ? N1 C4 C3 104.54(16) . . ? C13 C4 C3 117.01(18) . . ? N1 C4 H4 105.8 . . ? C13 C4 H4 105.8 . . ? C3 C4 H4 105.8 . . ? C10 C5 C6 118.8(2) . . ? C10 C5 C1 119.8(2) . . ? C6 C5 C1 121.3(2) . . ? C7 C6 C5 120.2(2) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C8 C7 C6 120.2(2) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C9 C8 C7 120.0(2) . . ? C9 C8 H8 120 . . ? C7 C8 H8 120 . . ? C8 C9 C10 120.1(2) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C9 C10 C5 120.7(2) . . ? C9 C10 H10 119.7 . . ? C5 C10 H10 119.7 . . ? O2 C11 O3 125.7(2) . . ? O2 C11 C3 124.4(2) . . ? O3 C11 C3 109.95(18) . . ? O3 C12 H12A 109.5 . . ? O3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C18 C13 C14 118.6(2) . . ? C18 C13 C4 123.85(18) . . ? C14 C13 C4 117.42(19) . . ? C15 C14 C13 121.4(2) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C16 C15 C14 118.8(2) . . ? C16 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? C17 C16 C15 120.9(2) . . ? C17 C16 Cl 119.68(18) . . ? C15 C16 Cl 119.37(18) . . ? C16 C17 C18 119.8(2) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C13 C18 C17 120.5(2) . . ? C13 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C24 C19 C20 119.7(2) . . ? C24 C19 N1 122.4(2) . . ? C20 C19 N1 117.86(19) . . ? C21 C20 C19 120.4(2) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C20 C21 C22 120.4(2) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C23 C22 C21 119.1(2) . . ? C23 C22 H22 120.4 . . ? C21 C22 H22 120.4 . . ? C22 C23 C24 121.4(2) . . ? C22 C23 H23 119.3 . . ? C24 C23 H23 119.3 . . ? C19 C24 C23 119.1(2) . . ? C19 C24 H24 120.5 . . ? C23 C24 H24 120.5 . . ? C19 N1 O1 108.55(15) . . ? C19 N1 C4 114.04(16) . . ? O1 N1 C4 110.27(15) . . ? O4 N2 O5 124.5(2) . . ? O4 N2 C3 118.83(19) . . ? O5 N2 C3 116.61(18) . . ? C1 O1 N1 106.74(14) . . ? C11 O3 C12 115.9(2) . . ? 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 O1 C1 C2 C3 58.3(2) . . . . ? C5 C1 C2 C3 177.31(17) . . . . ? C1 C2 C3 N2 -172.79(16) . . . . ? C1 C2 C3 C4 -52.8(2) . . . . ? C1 C2 C3 C11 70.0(2) . . . . ? C2 C3 C4 N1 54.2(2) . . . . ? N2 C3 C4 N1 175.45(16) . . . . ? C11 C3 C4 N1 -71.5(2) . . . . ? C2 C3 C4 C13 -76.7(2) . . . . ? N2 C3 C4 C13 44.6(2) . . . . ? C11 C3 C4 C13 157.60(18) . . . . ? O1 C1 C5 C10 -130.2(2) . . . . ? C2 C1 C5 C10 111.2(2) . . . . ? O1 C1 C5 C6 54.0(3) . . . . ? C2 C1 C5 C6 -64.6(3) . . . . ? C10 C5 C6 C7 -0.4(3) . . . . ? C1 C5 C6 C7 175.4(2) . . . . ? C5 C6 C7 C8 0.1(4) . . . . ? C6 C7 C8 C9 0.1(4) . . . . ? C7 C8 C9 C10 0.0(4) . . . . ? C8 C9 C10 C5 -0.4(4) . . . . ? C6 C5 C10 C9 0.5(4) . . . . ? C1 C5 C10 C9 -175.4(2) . . . . ? C2 C3 C11 O2 -144.5(2) . . . . ? N2 C3 C11 O2 95.4(2) . . . . ? C4 C3 C11 O2 -19.5(3) . . . . ? C2 C3 C11 O3 36.3(2) . . . . ? N2 C3 C11 O3 -83.7(2) . . . . ? C4 C3 C11 O3 161.37(18) . . . . ? N1 C4 C13 C18 -35.1(3) . . . . ? C3 C4 C13 C18 89.8(2) . . . . ? N1 C4 C13 C14 140.6(2) . . . . ? C3 C4 C13 C14 -94.4(2) . . . . ? C18 C13 C14 C15 -1.6(4) . . . . ? C4 C13 C14 C15 -177.6(2) . . . . ? C13 C14 C15 C16 0.7(4) . . . . ? C14 C15 C16 C17 0.9(4) . . . . ? C14 C15 C16 Cl -178.6(2) . . . . ? C15 C16 C17 C18 -1.5(4) . . . . ? Cl C16 C17 C18 178.02(17) . . . . ? C14 C13 C18 C17 0.9(3) . . . . ? C4 C13 C18 C17 176.6(2) . . . . ? C16 C17 C18 C13 0.6(3) . . . . ? C24 C19 C20 C21 0.1(3) . . . . ? N1 C19 C20 C21 -178.3(2) . . . . ? C19 C20 C21 C22 0.3(4) . . . . ? C20 C21 C22 C23 -0.5(4) . . . . ? C21 C22 C23 C24 0.2(4) . . . . ? C20 C19 C24 C23 -0.4(4) . . . . ? N1 C19 C24 C23 178.0(2) . . . . ? C22 C23 C24 C19 0.3(4) . . . . ? C24 C19 N1 O1 -0.1(3) . . . . ? C20 C19 N1 O1 178.28(18) . . . . ? C24 C19 N1 C4 123.2(2) . . . . ? C20 C19 N1 C4 -58.4(3) . . . . ? C13 C4 N1 C19 -55.4(2) . . . . ? C3 C4 N1 C19 173.59(17) . . . . ? C13 C4 N1 O1 67.0(2) . . . . ? C3 C4 N1 O1 -64.00(19) . . . . ? C2 C3 N2 O4 11.6(3) . . . . ? C4 C3 N2 O4 -111.0(2) . . . . ? C11 C3 N2 O4 133.8(2) . . . . ? C2 C3 N2 O5 -169.80(19) . . . . ? C4 C3 N2 O5 67.6(2) . . . . ? C11 C3 N2 O5 -47.5(2) . . . . ? C5 C1 O1 N1 171.87(16) . . . . ? C2 C1 O1 N1 -67.41(19) . . . . ? C19 N1 O1 C1 -160.70(16) . . . . ? C4 N1 O1 C1 73.72(19) . . . . ? O2 C11 O3 C12 4.2(4) . . . . ? C3 C11 O3 C12 -176.7(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C2 H2A Cl 0.99 2.93 3.535(2) 120.6 2_664 # END of CIF _database_code_depnum_ccdc_archive 'CCDC 945056'