# Electronic Supplementary Material (ESI) for Medicinal Chemistry 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_dm5clr #TrackingRef 'ccdc_deposit_13.cif' _audit_creation_date 2012-10-12T14:13:11-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C14 H15 Cl N2 O' _chemical_formula_weight 262.73 _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# 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 7.929(4) _cell_length_b 12.530(4) _cell_length_c 12.977(8) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1289.3(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 10 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_crystal_description needles _exptl_crystal_colour yellow _exptl_crystal_size_max 0.9 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.285 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details ; Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166 ; _exptl_absorpt_correction_T_min 0.3057 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_unetI/netI 0.0513 _diffrn_reflns_number 1806 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 1806 _reflns_number_gt 1010 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD-4 Software (Enraf Nonius, 1989)' _computing_cell_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 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^)+(0.0524P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_number_reflns 1806 _refine_ls_number_parameters 224 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0948 _refine_ls_R_factor_gt 0.041 _refine_ls_wR_factor_ref 0.1029 _refine_ls_wR_factor_gt 0.088 _refine_ls_goodness_of_fit_ref 0.949 _refine_ls_restrained_S_all 0.949 _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 -0.04(15) _refine_diff_density_max 0.142 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.04 #----------------------------------------------------------------------------# # 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' Cl Cl 0.1484 0.1585 '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 Cl1 Cl 0.8552(2) 0.75926(10) 0.47502(12) 0.0847(5) Uani 1 1 d . . . N2 N 0.9038(5) 0.3961(3) 0.4991(3) 0.0493(12) Uani 1 1 d . . . O1 O 0.8537(6) 0.5064(3) 0.7479(3) 0.0848(12) Uani 1 1 d . . . C5 C 0.8836(6) 0.2244(3) 0.4259(4) 0.0385(11) Uani 1 1 d . . . C3 C 0.9066(5) 0.2503(4) 0.6225(3) 0.0436(12) Uani 1 1 d . . . N1 N 0.9158(6) 0.4634(3) 0.5842(3) 0.0563(13) Uani 1 1 d . . . C4 C 0.8954(6) 0.2961(3) 0.5167(4) 0.0418(12) Uani 1 1 d . . . C2 C 0.8196(8) 0.3249(4) 0.6968(4) 0.0552(15) Uani 1 1 d . . . H2A H 0.688(6) 0.318(4) 0.682(4) 0.085(17) Uiso 1 1 d . . . H2B H 0.834(6) 0.306(3) 0.762(3) 0.061(16) Uiso 1 1 d . . . C8 C 0.8380(7) 0.1376(4) 0.6274(4) 0.0481(13) Uani 1 1 d . . . H8A H 0.704(5) 0.142(3) 0.613(3) 0.066(14) Uiso 1 1 d . . . H8B H 0.860(6) 0.105(3) 0.691(3) 0.053(14) Uiso 1 1 d . . . C9 C 0.8583(7) 0.2663(4) 0.3289(4) 0.0489(12) Uani 1 1 d . . . H9 H 0.843(5) 0.338(3) 0.318(3) 0.032(11) Uiso 1 1 d . . . C13 C 0.9558(9) 0.5731(4) 0.5564(5) 0.0706(19) Uani 1 1 d . . . H13A H 1.050(7) 0.573(4) 0.507(3) 0.09(2) Uiso 1 1 d . . . H13B H 0.967(7) 0.624(5) 0.630(4) 0.13(2) Uiso 1 1 d . . . C10 C 0.8520(8) 0.1996(5) 0.2449(4) 0.0632(14) Uani 1 1 d . . . H10 H 0.830(5) 0.229(3) 0.180(3) 0.056(13) Uiso 1 1 d . . . C7 C 0.9248(8) 0.0689(4) 0.5463(4) 0.0579(16) Uani 1 1 d . . . C6 C 0.8998(6) 0.1149(3) 0.4400(4) 0.0463(13) Uani 1 1 d . . . C1 C 0.8627(8) 0.4387(4) 0.6818(4) 0.0565(14) Uani 1 1 d . . . C12 C 0.8899(8) 0.0505(4) 0.3535(5) 0.0663(17) Uani 1 1 d . . . H12 H 0.916(6) -0.022(3) 0.368(3) 0.051(14) Uiso 1 1 d . . . C11 C 0.8682(9) 0.0912(5) 0.2579(5) 0.0728(17) Uani 1 1 d . . . H11 H 0.866(7) 0.037(3) 0.205(3) 0.075(15) Uiso 1 1 d . . . C14 C 0.8102(9) 0.6229(5) 0.5013(6) 0.078(2) Uani 1 1 d . . . H14A H 0.726(6) 0.610(3) 0.551(3) 0.059(18) Uiso 1 1 d . . . H14B H 0.754(8) 0.582(4) 0.439(4) 0.13(3) Uiso 1 1 d . . . H3 H 1.027(5) 0.251(4) 0.638(3) 0.059(13) Uiso 1 1 d . . . H7A H 1.074(7) 0.068(4) 0.563(4) 0.10(2) Uiso 1 1 d . . . H7B H 0.861(7) -0.002(4) 0.549(4) 0.096(18) 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 Cl1 0.0899(10) 0.0622(7) 0.1019(11) 0.0097(8) 0.0285(11) 0.0036(10) N2 0.053(3) 0.051(2) 0.044(3) -0.006(2) 0.003(3) 0.000(2) O1 0.100(3) 0.086(2) 0.068(2) -0.039(2) 0.004(3) -0.006(3) C5 0.022(3) 0.053(2) 0.041(3) -0.001(3) 0.003(3) -0.003(2) C3 0.031(3) 0.062(3) 0.038(3) 0.001(3) -0.003(3) 0.000(3) N1 0.066(3) 0.0462(19) 0.057(3) 0.000(2) -0.009(3) -0.002(2) C4 0.026(3) 0.057(2) 0.043(3) 0.010(2) 0.008(3) 0.000(2) C2 0.060(4) 0.069(3) 0.037(3) -0.003(3) 0.007(3) -0.003(3) C8 0.038(3) 0.058(3) 0.049(3) 0.013(3) -0.003(3) -0.003(3) C9 0.040(3) 0.066(3) 0.040(3) 0.003(3) 0.003(3) 0.006(4) C13 0.055(4) 0.068(3) 0.089(5) -0.008(4) 0.005(4) -0.010(3) C10 0.059(4) 0.094(4) 0.036(3) 0.011(3) 0.003(3) -0.009(4) C7 0.069(5) 0.054(3) 0.051(4) 0.004(3) 0.000(3) 0.003(3) C6 0.044(3) 0.055(3) 0.040(3) 0.000(3) 0.004(3) 0.001(3) C1 0.053(3) 0.067(3) 0.050(3) 0.001(3) 0.004(3) 0.001(3) C12 0.075(4) 0.066(4) 0.058(4) -0.012(3) 0.005(4) -0.014(4) C11 0.077(4) 0.091(4) 0.050(4) -0.021(4) 0.004(4) -0.030(4) C14 0.066(4) 0.064(3) 0.103(6) 0.006(4) -0.007(5) -0.008(3) #----------------------------------------------------------------------------# # 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 Cl1 C14 1.778(6) . ? N2 C4 1.276(5) . ? N2 N1 1.392(5) . ? O1 C1 1.209(5) . ? C5 C9 1.379(6) . ? C5 C6 1.390(6) . ? C5 C4 1.485(6) . ? C3 C4 1.490(6) . ? C3 C2 1.509(7) . ? C3 C8 1.514(6) . ? N1 C1 1.370(6) . ? N1 C13 1.456(6) . ? C2 C1 1.480(7) . ? C8 C7 1.525(7) . ? C9 C10 1.374(6) . ? C13 C14 1.494(8) . ? C10 C11 1.374(7) . ? C7 C6 1.508(7) . ? C6 C12 1.384(7) . ? C12 C11 1.352(7) . ? 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 C4 N2 N1 117.2(4) . . ? C9 C5 C6 120.7(5) . . ? C9 C5 C4 120.2(4) . . ? C6 C5 C4 119.1(4) . . ? C4 C3 C2 108.8(4) . . ? C4 C3 C8 112.1(4) . . ? C2 C3 C8 112.7(4) . . ? C1 N1 N2 125.1(4) . . ? C1 N1 C13 120.6(5) . . ? N2 N1 C13 113.0(4) . . ? N2 C4 C5 117.1(4) . . ? N2 C4 C3 122.7(5) . . ? C5 C4 C3 120.1(4) . . ? C1 C2 C3 114.0(5) . . ? C3 C8 C7 109.6(5) . . ? C10 C9 C5 119.8(5) . . ? N1 C13 C14 110.2(5) . . ? C9 C10 C11 120.1(5) . . ? C6 C7 C8 110.9(4) . . ? C12 C6 C5 117.5(5) . . ? C12 C6 C7 121.8(4) . . ? C5 C6 C7 120.7(5) . . ? O1 C1 N1 121.1(5) . . ? O1 C1 C2 124.7(5) . . ? N1 C1 C2 114.2(5) . . ? C11 C12 C6 122.1(5) . . ? C12 C11 C10 119.8(6) . . ? C13 C14 Cl1 109.8(4) . . ? # 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 906024'