# Electronic Supplementary Material (ESI) for Chemical Communications # 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_be17jea1n #TrackingRef 'ccdc_deposit_C17 H13 N O.cif' _audit_creation_date 2013-02-14T10:11:59-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common DDJS-52 _chemical_formula_moiety 'C17 H13 N O' _chemical_formula_sum 'C17 H13 N O' _chemical_formula_weight 247.28 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_Int_Tables_number 61 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' '-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 10.4675(7) _cell_length_b 12.2615(8) _cell_length_c 19.3299(11) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2480.9(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5891 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 27.52 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.14 _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9126 _exptl_absorpt_correction_T_max 0.9890 _exptl_absorpt_process_details 'BRUKER AXS - SADABS' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Bruker X8 kappa APEXII CCD' _diffrn_measurement_method 'omega and phi scans' _diffrn_reflns_av_R_equivalents 0.0602 _diffrn_reflns_av_unetI/netI 0.0314 _diffrn_reflns_number 42766 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 28.28 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 3081 _reflns_number_gt 2260 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 v2012.10-0 (Bruker AXS, 2012)' _computing_cell_refinement 'APEX2 v2012.10-0 (Bruker AXS, 2012)' _computing_data_reduction 'APEX2 v2012.10-0 (Bruker AXS, 2012)' _computing_structure_solution 'SIR97 (Giacovazzo et al, 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^)+(0.0568P)^2^+0.8072P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3081 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0671 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1213 _refine_ls_wR_factor_gt 0.1101 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.423 _refine_diff_density_min -0.24 _refine_diff_density_rms 0.053 #----------------------------------------------------------------------------# # 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 0.46890(13) 0.01757(11) 0.25623(7) 0.0194(3) Uani 1 1 d . . . C2 C 0.55303(14) 0.06592(12) 0.30088(7) 0.0213(3) Uani 1 1 d . . . H2 H 0.6079 0.1222 0.2848 0.026 Uiso 1 1 calc R . . C3 C 0.55875(14) 0.03249(12) 0.37106(8) 0.0225(3) Uani 1 1 d . . . H3 H 0.6176 0.0663 0.4017 0.027 Uiso 1 1 calc R . . C4 C 0.48002(14) -0.04812(12) 0.39491(7) 0.0205(3) Uani 1 1 d . . . H4 H 0.4847 -0.0702 0.442 0.025 Uiso 1 1 calc R . . C5 C 0.39120(13) -0.09909(11) 0.34960(7) 0.0179(3) Uani 1 1 d . . . C6 C 0.30778(14) -0.18224(12) 0.37275(8) 0.0217(3) Uani 1 1 d . . . H6 H 0.3112 -0.2051 0.4197 0.026 Uiso 1 1 calc R . . C7 C 0.22256(14) -0.23009(12) 0.32880(8) 0.0238(3) Uani 1 1 d . . . H7 H 0.1675 -0.2859 0.3453 0.029 Uiso 1 1 calc R . . C8 C 0.21576(14) -0.19714(12) 0.25916(8) 0.0226(3) Uani 1 1 d . . . H8 H 0.1558 -0.2307 0.229 0.027 Uiso 1 1 calc R . . C9 C 0.29461(14) -0.11738(11) 0.23453(7) 0.0202(3) Uani 1 1 d . . . H9 H 0.2898 -0.0963 0.1873 0.024 Uiso 1 1 calc R . . C10 C 0.38409(13) -0.06554(11) 0.27926(7) 0.0178(3) Uani 1 1 d . . . N11 N 0.45903(12) 0.05309(10) 0.18627(6) 0.0214(3) Uani 1 1 d . . . C12 C 0.55666(14) 0.04424(11) 0.14650(7) 0.0200(3) Uani 1 1 d . . . H12 H 0.6307 0.0079 0.1632 0.024 Uiso 1 1 calc R . . C13 C 0.55708(13) 0.08811(11) 0.07681(7) 0.0175(3) Uani 1 1 d . . . C14 C 0.45531(13) 0.15185(11) 0.05191(7) 0.0171(3) Uani 1 1 d . . . C15 C 0.46501(14) 0.20211(11) -0.01238(7) 0.0199(3) Uani 1 1 d . . . H15 H 0.3975 0.247 -0.0288 0.024 Uiso 1 1 calc R . . C16 C 0.57299(14) 0.18676(11) -0.05242(7) 0.0204(3) Uani 1 1 d . . . H16 H 0.5787 0.221 -0.0964 0.025 Uiso 1 1 calc R . . C17 C 0.67315(14) 0.12205(11) -0.02930(7) 0.0201(3) Uani 1 1 d . . . H17 H 0.7466 0.1113 -0.0574 0.024 Uiso 1 1 calc R . . C18 C 0.66469(14) 0.07362(11) 0.03494(7) 0.0193(3) Uani 1 1 d . . . H18 H 0.7332 0.0296 0.051 0.023 Uiso 1 1 calc R . . O19 O 0.34807(10) 0.16770(9) 0.08976(5) 0.0249(3) Uani 1 1 d . . . H19 H 0.360(2) 0.1284(19) 0.1318(12) 0.060(7) 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 0.0183(7) 0.0189(7) 0.0211(7) 0.0021(6) 0.0025(5) 0.0060(5) C2 0.0184(7) 0.0187(7) 0.0269(8) 0.0019(6) 0.0041(6) 0.0009(6) C3 0.0187(7) 0.0227(8) 0.0260(8) -0.0019(6) -0.0027(6) 0.0025(6) C4 0.0200(7) 0.0220(7) 0.0194(7) 0.0027(5) 0.0005(5) 0.0035(6) C5 0.0181(7) 0.0175(7) 0.0181(7) 0.0005(5) 0.0022(5) 0.0064(5) C6 0.0228(7) 0.0209(7) 0.0214(7) 0.0020(6) 0.0022(6) 0.0034(6) C7 0.0234(8) 0.0194(7) 0.0285(8) 0.0016(6) 0.0033(6) -0.0007(6) C8 0.0219(7) 0.0209(7) 0.0250(7) -0.0044(6) 0.0008(6) 0.0009(6) C9 0.0222(8) 0.0211(7) 0.0173(7) -0.0011(5) 0.0016(5) 0.0063(6) C10 0.0171(7) 0.0182(7) 0.0180(7) 0.0007(5) 0.0031(5) 0.0061(5) N11 0.0226(6) 0.0216(6) 0.0198(6) 0.0047(5) 0.0034(5) 0.0012(5) C12 0.0200(7) 0.0164(7) 0.0237(7) 0.0025(5) 0.0012(6) 0.0031(6) C13 0.0202(7) 0.0134(6) 0.0189(7) 0.0015(5) 0.0012(5) 0.0005(5) C14 0.0164(7) 0.0161(6) 0.0190(7) -0.0014(5) 0.0020(5) -0.0008(5) C15 0.0214(7) 0.0187(7) 0.0196(7) 0.0009(6) -0.0038(5) 0.0025(6) C16 0.0270(8) 0.0180(7) 0.0163(7) 0.0008(5) 0.0014(6) -0.0023(6) C17 0.0194(7) 0.0198(7) 0.0212(7) -0.0021(5) 0.0044(6) -0.0015(6) C18 0.0186(7) 0.0172(7) 0.0221(7) -0.0013(5) 0.0007(5) 0.0027(5) O19 0.0189(5) 0.0311(6) 0.0246(6) 0.0063(4) 0.0045(4) 0.0062(4) #----------------------------------------------------------------------------# # 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 C2 1.368(2) . ? C1 C10 1.423(2) . ? C1 N11 1.4244(18) . ? C2 C3 1.418(2) . ? C2 H2 0.95 . ? C3 C4 1.367(2) . ? C3 H3 0.95 . ? C4 C5 1.422(2) . ? C4 H4 0.95 . ? C5 C6 1.415(2) . ? C5 C10 1.4225(18) . ? C6 C7 1.365(2) . ? C6 H6 0.95 . ? C7 C8 1.407(2) . ? C7 H7 0.95 . ? C8 C9 1.365(2) . ? C8 H8 0.95 . ? C9 C10 1.424(2) . ? C9 H9 0.95 . ? N11 C12 1.2835(18) . ? C12 C13 1.4505(19) . ? C12 H12 0.95 . ? C13 C18 1.3984(19) . ? C13 C14 1.4061(19) . ? C14 O19 1.3539(16) . ? C14 C15 1.3908(19) . ? C15 C16 1.383(2) . ? C15 H15 0.95 . ? C16 C17 1.389(2) . ? C16 H16 0.95 . ? C17 C18 1.3794(19) . ? C17 H17 0.95 . ? C18 H18 0.95 . ? O19 H19 0.95(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 C2 C1 C10 120.97(13) . . ? C2 C1 N11 120.87(13) . . ? C10 C1 N11 118.08(13) . . ? C1 C2 C3 120.35(14) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C3 C2 120.40(14) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 120.28(13) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 121.69(12) . . ? C6 C5 C10 118.58(13) . . ? C4 C5 C10 119.72(13) . . ? C7 C6 C5 121.09(13) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 C8 120.34(14) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C9 C8 C7 120.57(14) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 120.37(13) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C5 C10 C1 118.26(13) . . ? C5 C10 C9 119.05(13) . . ? C1 C10 C9 122.68(12) . . ? C12 N11 C1 119.02(12) . . ? N11 C12 C13 121.83(13) . . ? N11 C12 H12 119.1 . . ? C13 C12 H12 119.1 . . ? C18 C13 C14 118.87(12) . . ? C18 C13 C12 119.52(13) . . ? C14 C13 C12 121.45(12) . . ? O19 C14 C15 118.67(12) . . ? O19 C14 C13 121.52(12) . . ? C15 C14 C13 119.79(12) . . ? C16 C15 C14 119.97(13) . . ? C16 C15 H15 120 . . ? C14 C15 H15 120 . . ? C15 C16 C17 120.98(13) . . ? C15 C16 H16 119.5 . . ? C17 C16 H16 119.5 . . ? C18 C17 C16 119.16(13) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C17 C18 C13 121.20(13) . . ? C17 C18 H18 119.4 . . ? C13 C18 H18 119.4 . . ? C14 O19 H19 106.1(14) . . ? 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 C10 C1 C2 C3 1.1(2) . . . . ? N11 C1 C2 C3 177.72(12) . . . . ? C1 C2 C3 C4 -0.2(2) . . . . ? C2 C3 C4 C5 -0.2(2) . . . . ? C3 C4 C5 C6 -179.56(13) . . . . ? C3 C4 C5 C10 -0.3(2) . . . . ? C4 C5 C6 C7 179.67(14) . . . . ? C10 C5 C6 C7 0.4(2) . . . . ? C5 C6 C7 C8 -0.2(2) . . . . ? C6 C7 C8 C9 0.3(2) . . . . ? C7 C8 C9 C10 -0.7(2) . . . . ? C6 C5 C10 C1 -179.56(12) . . . . ? C4 C5 C10 C1 1.13(19) . . . . ? C6 C5 C10 C9 -0.68(19) . . . . ? C4 C5 C10 C9 -179.99(12) . . . . ? C2 C1 C10 C5 -1.6(2) . . . . ? N11 C1 C10 C5 -178.26(12) . . . . ? C2 C1 C10 C9 179.60(13) . . . . ? N11 C1 C10 C9 2.9(2) . . . . ? C8 C9 C10 C5 0.8(2) . . . . ? C8 C9 C10 C1 179.66(13) . . . . ? C2 C1 N11 C12 62.47(19) . . . . ? C10 C1 N11 C12 -120.82(15) . . . . ? C1 N11 C12 C13 -174.06(12) . . . . ? N11 C12 C13 C18 -178.25(14) . . . . ? N11 C12 C13 C14 6.4(2) . . . . ? C18 C13 C14 O19 179.21(12) . . . . ? C12 C13 C14 O19 -5.4(2) . . . . ? C18 C13 C14 C15 -2.2(2) . . . . ? C12 C13 C14 C15 173.17(13) . . . . ? O19 C14 C15 C16 -179.52(13) . . . . ? C13 C14 C15 C16 1.8(2) . . . . ? C14 C15 C16 C17 -0.4(2) . . . . ? C15 C16 C17 C18 -0.7(2) . . . . ? C16 C17 C18 C13 0.3(2) . . . . ? C14 C13 C18 C17 1.1(2) . . . . ? C12 C13 C18 C17 -174.35(13) . . . . ? 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 O19 H19 N11 0.95(2) 1.74(2) 2.6084(16) 150(2) . # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF _database_code_depnum_ccdc_archive 'CCDC 925351'