# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 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_san604 _audit_creation_date 2012-03-09T11:39:31-00:00 _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 'Compound X' _chemical_formula_moiety 'C18 H20 N2 O1' _chemical_formula_sum 'C18 H20 N2 O' _chemical_formula_weight 280.36 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.13 _cell_length_b 6.355 _cell_length_c 13.522 _cell_angle_alpha 90 _cell_angle_beta 105.71 _cell_angle_gamma 90 _cell_volume 838 _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4635 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.425 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.111 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(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 -0.12204E-2 _diffrn_orient_matrix_ub_12 0.7897E-3 _diffrn_orient_matrix_ub_13 -0.741928E-1 _diffrn_orient_matrix_ub_21 0.102538 _diffrn_orient_matrix_ub_22 0.14916E-2 _diffrn_orient_matrix_ub_23 0.199291E-1 _diffrn_orient_matrix_ub_31 0.9659E-3 _diffrn_orient_matrix_ub_32 -0.15735 _diffrn_orient_matrix_ub_33 -0.1834E-3 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_unetI/netI 0.0505 _diffrn_reflns_number 5581 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.18 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.986 _reflns_number_total 3286 _reflns_number_gt 2830 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process ; Scaled and merged with Sortav R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # 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_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 ; 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 'calc w=1/[\s^2^(Fo^2^)+(0.0468P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3286 _refine_ls_number_parameters 203 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0458 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0893 _refine_ls_wR_factor_gt 0.085 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.8(12) _refine_diff_density_max 0.121 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.028 #----------------------------------------------------------------------------# # 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 1.27507(15) 0.3129(3) 0.45987(11) 0.0355(3) Uani 1 1 d . . . C2 C 1.21877(16) 0.5143(3) 0.45601(12) 0.0400(4) Uani 1 1 d . . . H2 H 1.2294 0.6088 0.4063 0.048 Uiso 1 1 calc R . . C2A C 1.25346(15) 0.1744(3) 0.53514(11) 0.0350(3) Uani 1 1 d . . . H2A H 1.2888 0.0386 0.5394 0.042 Uiso 1 1 calc R . . C3 C 1.14752(15) 0.5749(3) 0.52506(11) 0.0366(4) Uani 1 1 d . . . H3 H 1.1128 0.711 0.5212 0.044 Uiso 1 1 calc R . . C3A C 1.18067(15) 0.2373(2) 0.60264(11) 0.0332(3) Uani 1 1 d . . . H3A H 1.1677 0.1418 0.6513 0.04 Uiso 1 1 calc R . . C4 C 1.12566(14) 0.4396(2) 0.60048(10) 0.0306(3) Uani 1 1 d . . . C5 C 1.04822(13) 0.5131(3) 0.66956(10) 0.0330(3) Uani 1 1 d . . . H5 H 1.0234 0.6544 0.6636 0.04 Uiso 1 1 calc R . . C6 C 1.00773(13) 0.4029(3) 0.74115(10) 0.0325(3) Uani 1 1 d . . . H6 H 1.0249 0.259 0.747 0.039 Uiso 1 1 calc R . . C7 C 0.93852(13) 0.5018(3) 0.80887(10) 0.0303(3) Uani 1 1 d . . . H7 H 0.9193 0.6449 0.8011 0.036 Uiso 1 1 calc R . . C8 C 0.83391(14) 0.5221(2) 0.94393(11) 0.0315(3) Uani 1 1 d . . . H8 H 0.8543 0.672 0.9395 0.038 Uiso 1 1 calc R . . C9 C 0.88739(14) 0.4497(2) 1.05529(10) 0.0344(3) Uani 1 1 d . . . H9A H 0.8392 0.526 1.097 0.041 Uiso 1 1 calc R . . H9B H 0.8668 0.3014 1.0593 0.041 Uiso 1 1 calc R . . C10 C 0.67983(14) 0.4894(3) 0.90868(10) 0.0337(3) Uani 1 1 d . . . C11 C 0.59393(17) 0.6535(3) 0.91750(12) 0.0451(4) Uani 1 1 d . . . H11 H 0.6307 0.7829 0.9432 0.054 Uiso 1 1 calc R . . C11A C 0.62235(15) 0.2987(3) 0.86999(11) 0.0444(4) Uani 1 1 d . . . H11A H 0.679 0.1865 0.8647 0.053 Uiso 1 1 calc R . . C12 C 0.45192(18) 0.6246(4) 0.88771(14) 0.0595(6) Uani 1 1 d . . . H12 H 0.3944 0.7343 0.8948 0.071 Uiso 1 1 calc R . . C12A C 0.48116(17) 0.2734(4) 0.83911(13) 0.0592(5) Uani 1 1 d . . . H12A H 0.4436 0.1453 0.8122 0.071 Uiso 1 1 calc R . . C13 C 0.39694(18) 0.4362(4) 0.84819(13) 0.0623(6) Uani 1 1 d . . . H13 H 0.3023 0.4187 0.8275 0.075 Uiso 1 1 calc R . . C14 C 1.3671(2) 0.4009(3) 0.31547(13) 0.0567(5) Uani 1 1 d . . . H14A H 1.422 0.3373 0.2759 0.085 Uiso 1 1 calc R . . H14B H 1.4115 0.5262 0.3479 0.085 Uiso 1 1 calc R . . H14C H 1.2787 0.4363 0.2711 0.085 Uiso 1 1 calc R . . C14A C 1.40036(19) 0.0436(3) 0.39203(14) 0.0518(5) Uani 1 1 d . . . H14D H 1.4505 0.0329 0.3413 0.078 Uiso 1 1 calc R . . H14E H 1.3244 -0.0524 0.3754 0.078 Uiso 1 1 calc R . . H14F H 1.4597 0.0091 0.4584 0.078 Uiso 1 1 calc R . . N1 N 0.90238(12) 0.4014(2) 0.87921(9) 0.0321(3) Uani 1 1 d . . . N2 N 1.35054(15) 0.2539(2) 0.39360(11) 0.0499(4) Uani 1 1 d . . . O1 O 1.03012(11) 0.48018(18) 1.09654(8) 0.0398(3) Uani 1 1 d . . . H15 H 1.0478(18) 0.613(4) 1.0960(13) 0.051(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0364(8) 0.0411(9) 0.0298(7) -0.0027(7) 0.0103(6) -0.0049(7) C2 0.0457(9) 0.0398(9) 0.0369(7) 0.0091(7) 0.0151(6) -0.0042(8) C2A 0.0353(8) 0.0337(9) 0.0362(7) -0.0001(7) 0.0101(6) 0.0011(6) C3 0.0358(8) 0.0325(8) 0.0419(8) 0.0056(7) 0.0110(6) 0.0019(6) C3A 0.0347(8) 0.0337(8) 0.0319(7) 0.0063(6) 0.0099(6) -0.0004(7) C4 0.0275(7) 0.0322(9) 0.0313(6) 0.0015(6) 0.0063(5) -0.0013(6) C5 0.0286(7) 0.0327(8) 0.0373(7) 0.0013(7) 0.0079(5) 0.0021(6) C6 0.0279(7) 0.0328(8) 0.0371(7) -0.0006(7) 0.0095(5) 0.0013(6) C7 0.0271(7) 0.0283(8) 0.0350(7) 0.0017(6) 0.0077(5) 0.0002(6) C8 0.0329(7) 0.0267(8) 0.0377(7) -0.0003(6) 0.0142(6) 0.0019(6) C9 0.0347(7) 0.0314(9) 0.0367(7) -0.0025(6) 0.0091(6) -0.0034(7) C10 0.0342(7) 0.0418(9) 0.0277(6) 0.0039(7) 0.0128(5) 0.0048(7) C11 0.0462(10) 0.0526(11) 0.0417(8) 0.0064(8) 0.0208(7) 0.0132(8) C11A 0.0368(9) 0.0548(11) 0.0430(8) -0.0061(8) 0.0132(7) -0.0046(8) C12 0.0428(10) 0.0910(17) 0.0506(10) 0.0178(11) 0.0226(8) 0.0283(11) C12A 0.0397(10) 0.0903(17) 0.0479(9) -0.0110(10) 0.0124(8) -0.0142(11) C13 0.0332(9) 0.1111(19) 0.0418(9) 0.0036(11) 0.0085(7) 0.0003(12) C14 0.0739(12) 0.0639(12) 0.0427(9) -0.0033(9) 0.0338(8) -0.0119(10) C14A 0.0526(10) 0.0600(13) 0.0468(9) -0.0045(9) 0.0205(8) 0.0083(9) N1 0.0319(6) 0.0293(6) 0.0367(6) -0.0012(5) 0.0123(5) 0.0019(5) N2 0.0679(9) 0.0457(9) 0.0473(8) -0.0037(7) 0.0348(7) -0.0040(8) O1 0.0350(6) 0.0306(7) 0.0494(6) -0.0035(5) 0.0038(4) -0.0001(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 N2 1.3780(18) . ? C1 C2 1.396(2) . ? C1 C2A 1.407(2) . ? C2 C3 1.381(2) . ? C2 H2 0.93 . ? C2A C3A 1.379(2) . ? C2A H2A 0.93 . ? C3 C4 1.397(2) . ? C3 H3 0.93 . ? C3A C4 1.398(2) . ? C3A H3A 0.93 . ? C4 C5 1.4503(19) . ? C5 C6 1.346(2) . ? C5 H5 0.93 . ? C6 C7 1.4399(19) . ? C6 H6 0.93 . ? C7 N1 1.2785(18) . ? C7 H7 0.93 . ? C8 N1 1.4711(17) . ? C8 C10 1.5177(19) . ? C8 C9 1.5266(19) . ? C8 H8 0.98 . ? C9 O1 1.4150(17) . ? C9 H9A 0.97 . ? C9 H9B 0.97 . ? C10 C11 1.384(2) . ? C10 C11A 1.384(2) . ? C11 C12 1.397(2) . ? C11 H11 0.93 . ? C11A C12A 1.387(2) . ? C11A H11A 0.93 . ? C12 C13 1.367(4) . ? C12 H12 0.93 . ? C12A C13 1.368(3) . ? C12A H12A 0.93 . ? C13 H13 0.93 . ? C14 N2 1.453(2) . ? C14 H14A 0.96 . ? C14 H14B 0.96 . ? C14 H14C 0.96 . ? C14A N2 1.431(2) . ? C14A H14D 0.96 . ? C14A H14E 0.96 . ? C14A H14F 0.96 . ? O1 H15 0.87(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 N2 C1 C2 121.18(14) . . ? N2 C1 C2A 121.53(15) . . ? C2 C1 C2A 117.28(13) . . ? C3 C2 C1 120.91(14) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C3A C2A C1 120.91(14) . . ? C3A C2A H2A 119.5 . . ? C1 C2A H2A 119.5 . . ? C2 C3 C4 122.48(15) . . ? C2 C3 H3 118.8 . . ? C4 C3 H3 118.8 . . ? C2A C3A C4 122.28(13) . . ? C2A C3A H3A 118.9 . . ? C4 C3A H3A 118.9 . . ? C3 C4 C3A 116.13(13) . . ? C3 C4 C5 119.48(14) . . ? C3A C4 C5 124.39(13) . . ? C6 C5 C4 128.24(15) . . ? C6 C5 H5 115.9 . . ? C4 C5 H5 115.9 . . ? C5 C6 C7 121.73(15) . . ? C5 C6 H6 119.1 . . ? C7 C6 H6 119.1 . . ? N1 C7 C6 122.82(14) . . ? N1 C7 H7 118.6 . . ? C6 C7 H7 118.6 . . ? N1 C8 C10 110.63(11) . . ? N1 C8 C9 109.34(12) . . ? C10 C8 C9 109.18(11) . . ? N1 C8 H8 109.2 . . ? C10 C8 H8 109.2 . . ? C9 C8 H8 109.2 . . ? O1 C9 C8 113.53(11) . . ? O1 C9 H9A 108.9 . . ? C8 C9 H9A 108.9 . . ? O1 C9 H9B 108.9 . . ? C8 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C11 C10 C11A 118.84(14) . . ? C11 C10 C8 119.13(15) . . ? C11A C10 C8 122.01(14) . . ? C10 C11 C12 119.88(19) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C10 C11A C12A 120.63(17) . . ? C10 C11A H11A 119.7 . . ? C12A C11A H11A 119.7 . . ? C13 C12 C11 120.45(19) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C13 C12A C11A 120.2(2) . . ? C13 C12A H12A 119.9 . . ? C11A C12A H12A 119.9 . . ? C12 C13 C12A 119.99(16) . . ? C12 C13 H13 120 . . ? C12A C13 H13 120 . . ? N2 C14 H14A 109.5 . . ? N2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N2 C14A H14D 109.5 . . ? N2 C14A H14E 109.5 . . ? H14D C14A H14E 109.5 . . ? N2 C14A H14F 109.5 . . ? H14D C14A H14F 109.5 . . ? H14E C14A H14F 109.5 . . ? C7 N1 C8 117.29(12) . . ? C1 N2 C14A 121.57(14) . . ? C1 N2 C14 119.44(15) . . ? C14A N2 C14 118.62(14) . . ? C9 O1 H15 108.8(12) . . ? 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 O1 H15 N1 0.87(2) 1.90(2) 2.7603(18) 169.8(17) 2_757 # END of CIF _database_code_depnum_ccdc_archive 'CCDC 953089' ####################################################################### # # 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_san560 _audit_creation_date 2012-03-04T22:28:12-00:00 _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 'san557 mario' _chemical_formula_moiety 'C18 H20 N2 O1' _chemical_formula_sum 'C18 H20 N2 O' _chemical_formula_weight 280.36 _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 6.1828(2) _cell_length_b 14.6917(8) _cell_length_c 16.9541(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1540.04(11) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5386 _cell_measurement_theta_min 2.91 _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 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.209 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.9416 _exptl_absorpt_correction_T_max 1.0222 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 298(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 0.59718E-1 _diffrn_orient_matrix_ub_12 -0.500225E-1 _diffrn_orient_matrix_ub_13 -0.335514E-1 _diffrn_orient_matrix_ub_21 -0.701233E-1 _diffrn_orient_matrix_ub_22 0.275788E-1 _diffrn_orient_matrix_ub_23 -0.47475E-1 _diffrn_orient_matrix_ub_31 0.132951 _diffrn_orient_matrix_ub_32 0.370148E-1 _diffrn_orient_matrix_ub_33 -0.99697E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0648 _diffrn_reflns_av_unetI/netI 0.0642 _diffrn_reflns_number 11063 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.973 _diffrn_measured_fraction_theta_max 0.973 _reflns_number_total 3393 _reflns_number_gt 2339 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process ; Scaled and merged with Sortav R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # 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_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 ; 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 'calc w=1/[\s^2^(Fo^2^)+(0.0484P)^2^+0.2247P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3393 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0944 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.1213 _refine_ls_wR_factor_gt 0.1051 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(2) _refine_diff_density_max 0.118 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.033 #----------------------------------------------------------------------------# # 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 0.9784(4) 0.97738(16) 0.45551(13) 0.0435(5) Uani 1 1 d . . . C2 C 0.7818(4) 0.94230(15) 0.48209(13) 0.0471(6) Uani 1 1 d . . . H6 H 0.6916 0.9786 0.5127 0.056 Uiso 1 1 calc R . . C2A C 1.1074(4) 0.91934(15) 0.41000(13) 0.0469(6) Uani 1 1 d . . . H2 H 1.2395 0.9403 0.3911 0.056 Uiso 1 1 calc R . . C3 C 0.7195(4) 0.85534(15) 0.46384(13) 0.0457(6) Uani 1 1 d . . . H5 H 0.587 0.8344 0.4825 0.055 Uiso 1 1 calc R . . C3A C 1.0434(4) 0.83207(15) 0.39252(13) 0.0439(5) Uani 1 1 d . . . H3 H 1.1343 0.7954 0.3625 0.053 Uiso 1 1 calc R . . C4 C 0.8463(3) 0.79681(14) 0.41841(11) 0.0375(5) Uani 1 1 d . . . C5 C 0.7712(4) 0.70548(14) 0.40170(12) 0.0404(5) Uani 1 1 d . . . H7 H 0.6338 0.6913 0.4203 0.049 Uiso 1 1 calc R . . C6 C 0.8735(4) 0.63904(15) 0.36307(12) 0.0431(5) Uani 1 1 d . . . H8 H 1.0109 0.6499 0.3428 0.052 Uiso 1 1 calc R . . C7 C 0.7763(4) 0.55129(15) 0.35215(12) 0.0411(5) Uani 1 1 d . . . H9 H 0.6371 0.5418 0.3712 0.049 Uiso 1 1 calc R . . C8 C 0.7687(4) 0.40010(14) 0.30687(12) 0.0412(5) Uani 1 1 d . . . C9 C 0.5643(3) 0.39049(14) 0.27234(12) 0.0394(5) Uani 1 1 d . . . C10 C 0.4327(4) 0.46945(16) 0.24281(14) 0.0500(6) Uani 1 1 d . . . H16A H 0.5283 0.513 0.2177 0.06 Uiso 1 1 calc R . . H16B H 0.3317 0.4478 0.2032 0.06 Uiso 1 1 calc R . . C11 C 0.4846(4) 0.30324(16) 0.26184(14) 0.0517(6) Uani 1 1 d . . . H14 H 0.3488 0.2957 0.2391 0.062 Uiso 1 1 calc R . . C12 C 0.5999(5) 0.22726(17) 0.28397(16) 0.0650(8) Uani 1 1 d . . . H13 H 0.5422 0.1695 0.2765 0.078 Uiso 1 1 calc R . . C13 C 0.8002(5) 0.23756(18) 0.31712(16) 0.0653(8) Uani 1 1 d . . . H12 H 0.879 0.1866 0.3324 0.078 Uiso 1 1 calc R . . C14 C 0.8851(4) 0.32331(17) 0.32790(14) 0.0551(6) Uani 1 1 d . . . H11 H 1.0225 0.3297 0.3496 0.066 Uiso 1 1 calc R . . C15 C 0.9043(5) 1.12471(17) 0.51736(16) 0.0644(7) Uani 1 1 d . . . H18A H 0.7799 1.1394 0.486 0.097 Uiso 1 1 calc R . . H18B H 0.9814 1.1795 0.53 0.097 Uiso 1 1 calc R . . H18C H 0.8587 1.0954 0.5651 0.097 Uiso 1 1 calc R . . C15A C 1.2442(5) 1.1000(2) 0.4463(2) 0.0862(10) Uani 1 1 d . . . H17A H 1.3597 1.0607 0.4627 0.129 Uiso 1 1 calc R . . H17B H 1.2662 1.1597 0.4679 0.129 Uiso 1 1 calc R . . H17C H 1.2418 1.1036 0.3898 0.129 Uiso 1 1 calc R . . N1 N 0.8735(3) 0.48508(13) 0.31708(11) 0.0479(5) Uani 1 1 d . . . N2 N 1.0435(4) 1.06449(14) 0.47378(14) 0.0605(6) Uani 1 1 d . . . O1 O 0.3153(3) 0.51412(13) 0.30376(12) 0.0624(5) Uani 1 1 d . . . H1 H 0.164(6) 0.501(2) 0.298(2) 0.109(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0483(13) 0.0389(12) 0.0431(12) -0.0032(10) -0.0005(10) -0.0035(10) C2 0.0479(14) 0.0429(13) 0.0503(13) -0.0079(10) 0.0109(11) 0.0043(11) C2A 0.0424(13) 0.0428(14) 0.0556(14) -0.0051(10) 0.0097(11) -0.0066(11) C3 0.0421(13) 0.0445(13) 0.0505(13) -0.0010(10) 0.0091(11) -0.0013(11) C3A 0.0415(12) 0.0399(12) 0.0503(12) -0.0080(10) 0.0098(10) -0.0007(10) C4 0.0391(12) 0.0373(12) 0.0362(11) -0.0003(9) -0.0012(9) -0.0015(10) C5 0.0367(11) 0.0424(12) 0.0423(11) 0.0006(10) -0.0021(10) -0.0056(10) C6 0.0376(12) 0.0445(13) 0.0473(12) -0.0071(10) 0.0004(10) -0.0087(10) C7 0.0337(11) 0.0430(13) 0.0465(12) -0.0054(10) -0.0009(10) -0.0059(10) C8 0.0398(12) 0.0377(12) 0.0460(12) -0.0069(10) 0.0072(10) -0.0020(10) C9 0.0381(12) 0.0359(12) 0.0441(11) -0.0061(10) 0.0068(9) -0.0032(10) C10 0.0445(13) 0.0500(14) 0.0556(14) -0.0105(11) -0.0015(11) 0.0040(11) C11 0.0531(14) 0.0463(14) 0.0556(14) -0.0113(11) 0.0033(11) -0.0126(12) C12 0.087(2) 0.0363(14) 0.0720(17) -0.0058(12) 0.0070(16) -0.0138(14) C13 0.092(2) 0.0415(15) 0.0629(16) 0.0036(12) -0.0010(15) 0.0144(15) C14 0.0514(15) 0.0525(16) 0.0615(15) -0.0051(11) -0.0056(12) 0.0065(12) C15 0.0820(19) 0.0428(14) 0.0685(16) -0.0130(12) -0.0024(15) 0.0042(14) C15A 0.070(2) 0.0530(18) 0.135(3) -0.0199(18) 0.019(2) -0.0161(16) N1 0.0363(10) 0.0429(11) 0.0646(12) -0.0140(9) 0.0041(9) -0.0070(9) N2 0.0622(14) 0.0409(11) 0.0784(14) -0.0147(10) 0.0100(12) -0.0071(10) O1 0.0356(9) 0.0667(12) 0.0848(12) -0.0322(10) 0.0019(8) 0.0019(8) #----------------------------------------------------------------------------# # 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 N2 1.377(3) . ? C1 C2 1.395(3) . ? C1 C2A 1.399(3) . ? C2 C3 1.370(3) . ? C2A C3A 1.374(3) . ? C3 C4 1.396(3) . ? C3A C4 1.395(3) . ? C4 C5 1.448(3) . ? C5 C6 1.335(3) . ? C6 C7 1.435(3) . ? C7 N1 1.289(3) . ? C8 C14 1.385(3) . ? C8 C9 1.400(3) . ? C8 N1 1.417(3) . ? C9 C11 1.385(3) . ? C9 C10 1.503(3) . ? C10 O1 1.423(3) . ? C11 C12 1.377(4) . ? C12 C13 1.368(4) . ? C13 C14 1.377(4) . ? C15 N2 1.439(3) . ? C15A N2 1.424(4) . ? 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 N2 C1 C2 121.7(2) . . ? N2 C1 C2A 121.6(2) . . ? C2 C1 C2A 116.7(2) . . ? C3 C2 C1 121.1(2) . . ? C3A C2A C1 121.6(2) . . ? C2 C3 C4 122.8(2) . . ? C2A C3A C4 122.0(2) . . ? C3A C4 C3 115.8(2) . . ? C3A C4 C5 124.2(2) . . ? C3 C4 C5 119.91(19) . . ? C6 C5 C4 128.4(2) . . ? C5 C6 C7 121.5(2) . . ? N1 C7 C6 122.9(2) . . ? C14 C8 C9 119.7(2) . . ? C14 C8 N1 116.7(2) . . ? C9 C8 N1 123.54(19) . . ? C11 C9 C8 117.9(2) . . ? C11 C9 C10 118.6(2) . . ? C8 C9 C10 123.39(19) . . ? O1 C10 C9 113.0(2) . . ? C12 C11 C9 122.1(2) . . ? C13 C12 C11 119.4(2) . . ? C12 C13 C14 120.1(2) . . ? C13 C14 C8 120.8(2) . . ? C7 N1 C8 120.55(18) . . ? C1 N2 C15A 121.4(2) . . ? C1 N2 C15 120.8(2) . . ? C15A N2 C15 117.6(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 O1 H1 N1 0.96(4) 1.84(4) 2.774(2) 163(3) 1_455 # END of CIF _database_code_depnum_ccdc_archive 'CCDC 953090' ####################################################################### # # 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_san583 _audit_creation_date 2012-08-23T18:57:47-00:00 _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 'Compound X' _chemical_formula_moiety 'C18 H20 N2 O1' _chemical_formula_sum 'C18 H20 N2 O' _chemical_formula_weight 280.36 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system orthorhombic _space_group_name_H-M_alt p_21_c_a _space_group_name_Hall 'P -2ac 2a' _space_group_IT_number 29 loop_ _space_group_symop_operation_xyz 'x, y, z' 'x+1/2, -y, -z' 'x, -y, z+1/2' 'x+1/2, y, -z+1/2' _cell_length_a 7.80650(40) _cell_length_b 16.42600(140) _cell_length_c 12.12220(119) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 1554.424(218) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2487 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 19.98 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.198 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.9398 _exptl_absorpt_correction_T_max 1.0329 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(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 0.266467E-1 _diffrn_orient_matrix_ub_12 -0.592479E-1 _diffrn_orient_matrix_ub_13 0.80818E-2 _diffrn_orient_matrix_ub_21 0.612371E-1 _diffrn_orient_matrix_ub_22 0.8384E-3 _diffrn_orient_matrix_ub_23 -0.724477E-1 _diffrn_orient_matrix_ub_31 0.109312 _diffrn_orient_matrix_ub_32 0.13973E-1 _diffrn_orient_matrix_ub_33 0.386154E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0468 _diffrn_reflns_av_unetI/netI 0.0471 _diffrn_reflns_number 3602 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 19.98 _diffrn_reflns_theta_full 19.98 _diffrn_measured_fraction_theta_full 0.975 _diffrn_measured_fraction_theta_max 0.975 _reflns_number_total 1418 _reflns_number_gt 1249 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process ; Scaled and merged with Sortav R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # 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_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 ; 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 'calc w=1/[\s^2^(Fo^2^)+(0.0787P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 1418 _refine_ls_number_parameters 191 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0459 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.1046 _refine_ls_wR_factor_gt 0.0968 _refine_ls_goodness_of_fit_ref 0.968 _refine_ls_restrained_S_all 0.968 _refine_ls_shift/su_max 0.11 _refine_ls_shift/su_mean 0.009 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(3) _refine_diff_density_max 0.08 _refine_diff_density_min -0.095 _refine_diff_density_rms 0.021 #----------------------------------------------------------------------------# # 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 -0.1841(4) 1.0139(2) 0.3779(3) 0.0563(10) Uani 1 1 d . . . C2 C -0.1085(5) 0.9585(2) 0.4506(3) 0.0592(11) Uani 1 1 d . . . H12 H -0.0494 0.9776 0.5119 0.071 Uiso 1 1 calc R . . C2A C -0.2750(4) 0.9821(2) 0.2891(3) 0.0626(11) Uani 1 1 d . . . H14 H -0.3287 1.0172 0.2398 0.075 Uiso 1 1 calc R . . C3 C -0.1202(4) 0.8765(2) 0.4328(3) 0.0559(10) Uani 1 1 d . . . H11 H -0.0679 0.8411 0.4823 0.067 Uiso 1 1 calc R . . C3A C -0.2863(4) 0.8998(2) 0.2733(3) 0.0613(11) Uani 1 1 d . . . H15 H -0.3489 0.8805 0.2135 0.074 Uiso 1 1 calc R . . C4 C -0.2082(4) 0.8443(2) 0.3427(3) 0.0487(9) Uani 1 1 d . . . C5 C -0.2140(4) 0.7571(2) 0.3225(3) 0.0545(10) Uani 1 1 d . . . H9 H -0.1634 0.7243 0.376 0.065 Uiso 1 1 calc R . . C6 C -0.2833(4) 0.7181(2) 0.2364(3) 0.0560(10) Uani 1 1 d . . . H8 H -0.3374 0.7488 0.182 0.067 Uiso 1 1 calc R . . C7 C -0.2780(4) 0.6321(2) 0.2241(3) 0.0536(10) Uani 1 1 d . . . H7 H -0.2232 0.6011 0.2778 0.064 Uiso 1 1 calc R . . C8 C -0.3262(5) 0.5105(2) 0.1271(3) 0.0521(9) Uani 1 1 d . . . C9 C -0.1700(4) 0.4711(2) 0.1444(3) 0.0538(10) Uani 1 1 d . . . H1 H -0.077 0.5009 0.1702 0.065 Uiso 1 1 calc R . . C10 C -0.1507(5) 0.3889(2) 0.1239(3) 0.0553(10) Uani 1 1 d . . . C11 C -0.2924(5) 0.3454(2) 0.0871(3) 0.0626(10) Uani 1 1 d . . . H3 H -0.2825 0.2898 0.0745 0.075 Uiso 1 1 calc R . . C12 C -0.4466(5) 0.3832(3) 0.0690(3) 0.0666(11) Uani 1 1 d . . . H4 H -0.5397 0.3531 0.0439 0.08 Uiso 1 1 calc R . . C13 C -0.4640(5) 0.4658(3) 0.0878(3) 0.0626(11) Uani 1 1 d . . . H5 H -0.5681 0.4914 0.0741 0.075 Uiso 1 1 calc R . . C14 C 0.0195(5) 0.3492(2) 0.1379(3) 0.0696(11) Uani 1 1 d . . . H16A H 0.1042 0.3907 0.1544 0.084 Uiso 1 1 calc R . . H16B H 0.0142 0.3126 0.2006 0.084 Uiso 1 1 calc R . . C15 C -0.0813(6) 1.1317(3) 0.4847(4) 0.0945(15) Uani 1 1 d . . . H17A H -0.087 1.19 0.4801 0.142 Uiso 1 1 calc R . . H17B H 0.0362 1.1146 0.4828 0.142 Uiso 1 1 calc R . . H17C H -0.133 1.1139 0.5525 0.142 Uiso 1 1 calc R . . C15A C -0.2429(6) 1.1519(2) 0.3129(4) 0.0923(15) Uani 1 1 d . . . H18A H -0.2227 1.207 0.3359 0.139 Uiso 1 1 calc R . . H18B H -0.3639 1.1427 0.3067 0.139 Uiso 1 1 calc R . . H18C H -0.1895 1.1428 0.2426 0.139 Uiso 1 1 calc R . . N1 N -0.3465(4) 0.59552(18) 0.1411(3) 0.0574(8) Uani 1 1 d . . . N2 N -0.1715(4) 1.0966(2) 0.3932(3) 0.0767(11) Uani 1 1 d . . . O1 O 0.0740(3) 0.30474(15) 0.0442(2) 0.0682(8) Uani 1 1 d . . . H1A H 0.0805 0.3354 -0.009 0.100(18) Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.047(2) 0.059(3) 0.063(3) -0.002(2) -0.002(2) 0.0047(19) C2 0.054(2) 0.069(3) 0.055(3) -0.013(2) -0.005(2) -0.007(2) C2A 0.056(2) 0.060(3) 0.071(3) -0.001(2) -0.021(2) 0.0072(19) C3 0.051(2) 0.071(3) 0.046(2) -0.0030(19) -0.0044(18) 0.004(2) C3A 0.053(2) 0.064(3) 0.067(3) -0.006(2) -0.016(2) -0.002(2) C4 0.0417(18) 0.049(2) 0.056(2) -0.005(2) 0.003(2) 0.0005(16) C5 0.0417(18) 0.065(3) 0.057(3) 0.007(2) -0.0003(19) 0.0031(17) C6 0.057(2) 0.053(2) 0.057(3) -0.002(2) -0.012(2) 0.006(2) C7 0.051(2) 0.057(3) 0.053(3) 0.000(2) -0.0043(18) -0.0003(18) C8 0.060(2) 0.056(2) 0.040(2) 0.0029(18) -0.0022(19) -0.001(2) C9 0.057(2) 0.058(3) 0.046(2) 0.0011(19) -0.0054(18) 0.0010(19) C10 0.067(3) 0.057(3) 0.042(2) -0.0025(19) 0.0028(19) 0.004(2) C11 0.075(3) 0.056(2) 0.057(2) -0.0103(19) -0.001(2) -0.002(3) C12 0.070(3) 0.065(3) 0.065(3) -0.008(2) -0.007(2) -0.010(2) C13 0.058(3) 0.074(3) 0.056(3) -0.003(2) -0.009(2) 0.004(2) C14 0.082(3) 0.076(3) 0.050(2) -0.011(2) 0.002(2) 0.019(2) C15 0.109(4) 0.075(3) 0.100(4) -0.016(3) -0.012(3) -0.011(3) C15A 0.093(3) 0.062(3) 0.122(4) -0.004(3) -0.013(3) 0.013(2) N1 0.0627(19) 0.051(2) 0.058(2) 0.0008(16) -0.0052(17) 0.0013(14) N2 0.086(3) 0.055(2) 0.089(3) -0.011(2) -0.020(2) 0.0047(18) O1 0.0884(19) 0.0535(17) 0.0625(18) -0.0041(16) 0.0095(15) 0.0148(13) #----------------------------------------------------------------------------# # 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 N2 1.375(5) . ? C1 C2A 1.391(5) . ? C1 C2 1.397(5) . ? C2 C3 1.367(5) . ? C2A C3A 1.367(5) . ? C3 C4 1.394(5) . ? C3A C4 1.382(5) . ? C4 C5 1.454(5) . ? C5 C6 1.339(5) . ? C6 C7 1.422(5) . ? C7 N1 1.288(4) . ? C8 C13 1.387(5) . ? C8 C9 1.396(5) . ? C8 N1 1.416(5) . ? C9 C10 1.381(5) . ? C10 C11 1.391(5) . ? C10 C14 1.490(5) . ? C11 C12 1.371(5) . ? C12 C13 1.383(5) . ? C14 O1 1.415(4) . ? C15 N2 1.434(6) . ? C15A N2 1.444(5) . ? 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 N2 C1 C2A 120.8(4) . . ? N2 C1 C2 121.9(4) . . ? C2A C1 C2 117.3(3) . . ? C3 C2 C1 120.9(3) . . ? C3A C2A C1 120.8(3) . . ? C2 C3 C4 122.0(3) . . ? C2A C3A C4 122.6(3) . . ? C3A C4 C3 116.3(3) . . ? C3A C4 C5 122.3(3) . . ? C3 C4 C5 121.4(3) . . ? C6 C5 C4 127.9(3) . . ? C5 C6 C7 123.0(3) . . ? N1 C7 C6 122.2(3) . . ? C13 C8 C9 118.9(3) . . ? C13 C8 N1 118.5(3) . . ? C9 C8 N1 122.4(3) . . ? C10 C9 C8 121.4(3) . . ? C9 C10 C11 118.2(3) . . ? C9 C10 C14 120.4(3) . . ? C11 C10 C14 121.4(3) . . ? C12 C11 C10 121.1(3) . . ? C11 C12 C13 120.2(4) . . ? C12 C13 C8 120.0(4) . . ? O1 C14 C10 113.7(3) . . ? C7 N1 C8 120.5(3) . . ? C1 N2 C15 122.5(4) . . ? C1 N2 C15A 120.2(4) . . ? C15 N2 C15A 117.3(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 C13 C7 N1 98.6(6) . . . . ? N1 C7 C6 C5 179.4(3) . . . . ? C2 C1 N2 C15 -0.4(6) . . . . ? C2A C1 N2 C15A -4.3(5) . . . . ? C10 C14 O1 H1 55.5 . . . . ? 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 O1 H1A N1 0.82 2.04 2.849(4) 167.1 2_565 # END of CIF _database_code_depnum_ccdc_archive 'CCDC 953091'