# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_jp218f3-a0 _database_code_depnum_ccdc_archive 'CCDC 885441' #TrackingRef '11708_web_deposit_cif_file_0_Tripier_1338988938.jp218f3-a0_cifdep.cif' _audit_creation_date 2010-11-23T16:11:30-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _chemical_name_systematic ; ? ; _chemical_formula_sum 'C25 H21 N O4' _chemical_formula_weight 399.43 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -C2yc _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.0913(17) _cell_length_b 10.8393(9) _cell_length_c 13.9585(15) _cell_angle_alpha 90 _cell_angle_beta 110.917(13) _cell_angle_gamma 90 _cell_volume 1991.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 1597 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 29.57 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description parallelepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 -1 0 0.045 -1 1 0 0.035 -1 -1 0 0.05 1 1 0 0.05 0 0 -1 0.05 0 0 1 0.06 2 -1 -1 0.065 1 1 -4 0.05 -1 -3 2 0.06 -1 1 2 0.055 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.09 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'sealed X-ray tube' _diffrn_ambient_temperature 170(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 8.3622 _diffrn_orient_matrix_ub_11 0.0499078868 _diffrn_orient_matrix_ub_12 -0.0245904745 _diffrn_orient_matrix_ub_13 0.0195451 _diffrn_orient_matrix_ub_21 0.0064537639 _diffrn_orient_matrix_ub_22 0.0242043907 _diffrn_orient_matrix_ub_23 0.0491422255 _diffrn_orient_matrix_ub_31 -0.0192808137 _diffrn_orient_matrix_ub_32 -0.0555863892 _diffrn_orient_matrix_ub_33 0.0127664168 _diffrn_measurement_device 'Kappa-geometry diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method ; 4 stepped omega-scans over 115 deg. with kappa -79 deg. (chi -58.3 deg.), phi 0, 90, 180, 270 deg. step 1 deg., exposure time 45 s detector distance 50 mm detector angle 30 deg. ; _diffrn_reflns_av_R_equivalents 0.0693 _diffrn_reflns_av_unetI/netI 0.1024 _diffrn_reflns_number 8568 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.5 _diffrn_reflns_theta_max 28.28 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 2465 _reflns_number_gt 1180 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 1980-2002)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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. 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 'calc w=1/[\s^2^(Fo^2^)+(0.0306P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2465 _refine_ls_number_parameters 139 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1458 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.0989 _refine_ls_wR_factor_gt 0.076 _refine_ls_goodness_of_fit_ref 0.911 _refine_ls_restrained_S_all 0.911 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.211 _refine_diff_density_min -0.157 _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' 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 0.28788(17) 0.1353(2) -0.08725(16) 0.0407(6) Uani 1 1 d . . . H1A H 0.2677 0.0882 -0.1513 0.061 Uiso 1 1 calc R . . H1B H 0.277 0.2235 -0.103 0.061 Uiso 1 1 calc R . . H1C H 0.247 0.1092 -0.047 0.061 Uiso 1 1 calc R . . C2 C 0.39802(17) 0.11274(19) -0.02685(16) 0.0347(6) Uani 1 1 d . . . H2A H 0.4092 0.0233 -0.0128 0.042 Uiso 1 1 calc R . . H2B H 0.4391 0.1386 -0.0679 0.042 Uiso 1 1 calc R . . C3 C 0.44932(15) 0.29974(19) 0.06331(17) 0.0260(5) Uani 1 1 d . . . C4 C 0.47716(14) 0.36680(17) 0.16321(15) 0.0218(5) Uani 1 1 d . . . C5 C 0.47726(15) 0.49514(18) 0.15975(16) 0.0256(5) Uani 1 1 d . . . H5 H 0.4619 0.5367 0.0961 0.031 Uiso 1 1 calc R . . C6 C 0.5 0.5620(3) 0.25 0.0233(7) Uani 1 2 d S . . C7 C 0.5 0.7004(2) 0.25 0.0237(7) Uani 1 2 d S . . C8 C 0.40757(16) 0.76506(18) 0.20706(16) 0.0257(5) Uani 1 1 d . . . C9 C 0.31164(17) 0.7047(2) 0.16524(17) 0.0350(6) Uani 1 1 d . . . H9 H 0.3089 0.6172 0.1662 0.042 Uiso 1 1 calc R . . C10 C 0.22426(17) 0.7699(2) 0.12407(18) 0.0428(7) Uani 1 1 d . . . H10 H 0.1615 0.7272 0.0961 0.051 Uiso 1 1 calc R . . C11 C 0.22493(18) 0.9001(2) 0.12210(18) 0.0386(6) Uani 1 1 d . . . H11 H 0.1632 0.9445 0.0923 0.046 Uiso 1 1 calc R . . C12 C 0.31411(18) 0.96123(19) 0.16297(16) 0.0330(6) Uani 1 1 d . . . H12 H 0.3139 1.0489 0.1625 0.04 Uiso 1 1 calc R . . C13 C 0.40852(16) 0.89743(17) 0.20685(16) 0.0252(5) Uani 1 1 d . . . C14 C 0.5 0.9597(3) 0.25 0.0289(8) Uani 1 2 d S . . H14 H 0.5 1.0473 0.25 0.035 Uiso 1 2 calc SR . . N1 N 0.5 0.3012(2) 0.25 0.0243(6) Uani 1 2 d S . . O1 O 0.43176(10) 0.18025(12) 0.07013(10) 0.0298(4) Uani 1 1 d . . . O2 O 0.44240(12) 0.35088(13) -0.01556(11) 0.0419(4) 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 0.0404(15) 0.0437(15) 0.0353(14) -0.0098(11) 0.0101(11) -0.0052(12) C2 0.0418(15) 0.0277(13) 0.0360(14) -0.0095(11) 0.0157(11) -0.0022(11) C3 0.0251(13) 0.0234(12) 0.0307(13) 0.0014(10) 0.0113(10) -0.0018(9) C4 0.0182(11) 0.0212(12) 0.0262(12) -0.0006(10) 0.0083(9) -0.0006(9) C5 0.0258(12) 0.0224(12) 0.0278(12) 0.0025(10) 0.0086(9) -0.0017(10) C6 0.0176(16) 0.0226(16) 0.0271(18) 0 0.0047(13) 0 C7 0.0283(18) 0.0192(16) 0.0227(17) 0 0.0081(14) 0 C8 0.0287(13) 0.0233(12) 0.0243(12) -0.0017(10) 0.0085(10) 0.0001(10) C9 0.0301(13) 0.0276(13) 0.0447(15) 0.0005(11) 0.0103(11) 0.0016(11) C10 0.0266(15) 0.0438(16) 0.0524(17) -0.0019(13) 0.0075(12) 0.0021(12) C11 0.0350(16) 0.0395(16) 0.0392(15) 0.0069(12) 0.0106(12) 0.0116(11) C12 0.0395(15) 0.0259(13) 0.0357(15) 0.0064(11) 0.0160(11) 0.0068(11) C13 0.0309(13) 0.0227(12) 0.0234(12) 0.0016(10) 0.0114(10) 0.0027(10) C14 0.040(2) 0.0197(17) 0.0292(19) 0 0.0148(16) 0 N1 0.0207(14) 0.0226(14) 0.0278(15) 0 0.0066(11) 0 O1 0.0371(9) 0.0217(8) 0.0280(9) -0.0029(7) 0.0086(7) -0.0016(7) O2 0.0639(12) 0.0340(10) 0.0292(9) -0.0010(8) 0.0186(8) -0.0119(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 C2 1.498(3) . ? C1 H1A 0.98 . ? C1 H1B 0.98 . ? C1 H1C 0.98 . ? C2 O1 1.461(2) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 O2 1.205(2) . ? C3 O1 1.328(2) . ? C3 C4 1.495(3) . ? C4 N1 1.341(2) . ? C4 C5 1.392(3) . ? C5 C6 1.388(2) . ? C5 H5 0.95 . ? C6 C5 1.388(2) 2_655 ? C6 C7 1.501(4) . ? C7 C8 1.410(2) 2_655 ? C7 C8 1.410(2) . ? C8 C9 1.426(3) . ? C8 C13 1.435(2) . ? C9 C10 1.357(3) . ? C9 H9 0.95 . ? C10 C11 1.412(3) . ? C10 H10 0.95 . ? C11 C12 1.353(3) . ? C11 H11 0.95 . ? C12 C13 1.429(3) . ? C12 H12 0.95 . ? C13 C14 1.388(2) . ? C14 C13 1.388(2) 2_655 ? C14 H14 0.95 . ? N1 C4 1.341(2) 2_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C1 111.63(17) . . ? O1 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? O1 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 108 . . ? O2 C3 O1 123.9(2) . . ? O2 C3 C4 122.48(18) . . ? O1 C3 C4 113.62(18) . . ? N1 C4 C5 123.9(2) . . ? N1 C4 C3 118.90(17) . . ? C5 C4 C3 117.17(18) . . ? C6 C5 C4 119.5(2) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C5 117.1(3) . 2_655 ? C5 C6 C7 121.47(13) . . ? C5 C6 C7 121.47(13) 2_655 . ? C8 C7 C8 120.4(3) 2_655 . ? C8 C7 C6 119.78(13) 2_655 . ? C8 C7 C6 119.78(13) . . ? C7 C8 C9 122.88(19) . . ? C7 C8 C13 119.3(2) . . ? C9 C8 C13 117.8(2) . . ? C10 C9 C8 121.3(2) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C9 C10 C11 121.2(2) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C12 C11 C10 119.5(2) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C13 121.7(2) . . ? C11 C12 H12 119.1 . . ? C13 C12 H12 119.1 . . ? C14 C13 C12 121.95(19) . . ? C14 C13 C8 119.6(2) . . ? C12 C13 C8 118.5(2) . . ? C13 C14 C13 121.8(3) 2_655 . ? C13 C14 H14 119.1 2_655 . ? C13 C14 H14 119.1 . . ? C4 N1 C4 116.0(2) 2_655 . ? C3 O1 C2 115.42(16) . . ? #----------------------------------------------------------------------------# # END OF CIF # #----------------------------------------------------------------------------#