####################################################################### # # 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_05128a _database_code_depnum_ccdc_archive 'CCDC 621742' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H11 Br N2 O' _chemical_formula_weight 351.20 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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.5911(12) _cell_length_b 14.524(2) _cell_length_c 26.489(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2920.5(8) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 761 _cell_measurement_theta_min 2.908 _cell_measurement_theta_max 20.686 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.597 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 2.818 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.776 _exptl_absorpt_correction_T_max 0.928 _exptl_absorpt_process_details ; absorption correction based on 3617 reflections(SADABS);Rint 0.0690 before correction and 0.0465 after. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19679 _diffrn_reflns_av_R_equivalents 0.0930 _diffrn_reflns_av_sigmaI/netI 0.0705 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2559 _reflns_number_gt 1531 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; there is the presence of intramolecular hydrogen bonding; Hydrogen bonds with H..A < r(A) + 2.000 Angstroms and 110 deg. D-H d(D-H) d(H..A) 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^)+(0.0256P)^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 constrained _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2559 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0829 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.0776 _refine_ls_wR_factor_gt 0.0678 _refine_ls_goodness_of_fit_ref 0.868 _refine_ls_restrained_S_all 0.868 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 Br1 Br 0.00880(6) 0.62434(3) 0.305976(15) 0.04193(15) Uani 1 1 d . . . O1 O 0.0075(3) 0.47530(18) 0.43495(9) 0.0369(7) Uani 1 1 d . . . N1 N 0.3654(4) 0.5199(2) 0.35377(12) 0.0297(8) Uani 1 1 d . . . N2 N 0.2724(4) 0.5697(2) 0.48824(11) 0.0238(8) Uani 1 1 d . . . H2A H 0.1688 0.5494 0.4981 0.029 Uiso 1 1 calc R . . C1 C 0.2707(5) 0.5221(3) 0.39701(14) 0.0231(9) Uani 1 1 d . . . C2 C 0.5269(5) 0.5574(3) 0.35380(15) 0.0360(11) Uani 1 1 d . . . H2 H 0.5934 0.5548 0.3235 0.043 Uiso 1 1 calc R . . C3 C 0.6026(5) 0.5996(3) 0.39527(15) 0.0308(10) Uani 1 1 d . . . H3 H 0.7165 0.6263 0.3931 0.037 Uiso 1 1 calc R . . C4 C 0.5094(5) 0.6020(2) 0.43964(14) 0.0251(9) Uani 1 1 d . . . C5 C 0.5427(4) 0.6376(3) 0.48978(14) 0.0254(9) Uani 1 1 d . . . C6 C 0.6800(5) 0.6863(3) 0.51180(16) 0.0362(11) Uani 1 1 d . . . H6 H 0.7827 0.7015 0.4931 0.043 Uiso 1 1 calc R . . C7 C 0.6629(6) 0.7119(3) 0.56141(17) 0.0401(12) Uani 1 1 d . . . H7 H 0.7537 0.7471 0.5768 0.048 Uiso 1 1 calc R . . C8 C 0.5156(6) 0.6875(3) 0.58968(15) 0.0392(11) Uani 1 1 d . . . H8 H 0.5099 0.7048 0.6242 0.047 Uiso 1 1 calc R . . C9 C 0.3783(5) 0.6391(3) 0.56883(14) 0.0305(10) Uani 1 1 d . . . H9 H 0.2776 0.6226 0.5881 0.037 Uiso 1 1 calc R . . C10 C 0.3933(5) 0.6153(2) 0.51830(14) 0.0255(9) Uani 1 1 d . . . C11 C 0.3404(5) 0.5612(3) 0.44065(14) 0.0241(9) Uani 1 1 d . . . C12 C 0.0950(5) 0.4811(3) 0.39639(15) 0.0272(10) Uani 1 1 d . . . C13 C 0.0214(5) 0.4420(3) 0.34772(13) 0.0268(9) Uani 1 1 d . . . C14 C -0.0244(5) 0.4952(3) 0.30607(14) 0.0303(9) Uani 1 1 d . . . C15 C -0.1041(5) 0.4561(3) 0.26438(15) 0.0354(11) Uani 1 1 d . . . H15 H -0.1377 0.4936 0.2366 0.042 Uiso 1 1 calc R . . C16 C -0.1349(6) 0.3624(3) 0.26315(16) 0.0415(12) Uani 1 1 d . . . H16 H -0.1882 0.3350 0.2344 0.050 Uiso 1 1 calc R . . C17 C -0.0877(5) 0.3087(3) 0.30395(16) 0.0404(11) Uani 1 1 d . . . H17 H -0.1080 0.2442 0.3032 0.048 Uiso 1 1 calc R . . C18 C -0.0116(5) 0.3483(3) 0.34557(14) 0.0335(10) Uani 1 1 d . . . H18 H 0.0191 0.3107 0.3735 0.040 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 Br1 0.0462(3) 0.0371(2) 0.0425(3) 0.0069(2) 0.0026(3) 0.0036(3) O1 0.0310(16) 0.0553(19) 0.0244(15) -0.0053(13) 0.0065(16) -0.0088(17) N1 0.028(2) 0.036(2) 0.025(2) 0.0042(16) 0.0044(16) 0.0009(17) N2 0.0206(17) 0.028(2) 0.0233(19) 0.0013(16) 0.0034(15) -0.0029(15) C1 0.023(2) 0.024(2) 0.022(2) 0.0019(18) 0.0015(18) -0.0001(18) C2 0.031(3) 0.045(3) 0.033(3) 0.006(2) 0.013(2) 0.003(2) C3 0.024(2) 0.032(3) 0.036(3) 0.010(2) 0.002(2) -0.0046(19) C4 0.025(2) 0.022(2) 0.029(2) 0.0072(16) 0.001(2) -0.001(2) C5 0.022(2) 0.023(2) 0.031(2) 0.0078(19) -0.0031(18) -0.0003(18) C6 0.034(3) 0.032(3) 0.042(3) 0.007(2) -0.006(2) -0.007(2) C7 0.044(3) 0.029(3) 0.048(3) 0.003(2) -0.021(3) -0.011(2) C8 0.055(3) 0.030(2) 0.033(2) 0.0011(19) -0.010(3) -0.003(3) C9 0.033(2) 0.029(3) 0.030(3) -0.003(2) -0.0026(19) 0.002(2) C10 0.030(2) 0.018(2) 0.028(2) -0.0025(19) -0.0056(19) -0.0009(19) C11 0.026(2) 0.022(2) 0.024(2) 0.0031(19) 0.0026(19) 0.0027(19) C12 0.031(2) 0.027(2) 0.024(2) -0.0006(19) 0.002(2) 0.001(2) C13 0.021(2) 0.038(2) 0.021(2) -0.0027(18) 0.003(2) -0.002(2) C14 0.028(2) 0.034(2) 0.029(2) 0.000(2) 0.006(2) -0.001(2) C15 0.026(2) 0.059(3) 0.021(2) 0.004(2) 0.001(2) 0.005(2) C16 0.038(3) 0.057(4) 0.030(3) -0.014(3) -0.004(2) -0.008(3) C17 0.045(3) 0.037(3) 0.039(3) -0.004(2) 0.001(2) -0.003(2) C18 0.036(2) 0.036(2) 0.028(2) 0.0000(18) -0.004(2) 0.000(2) _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 Br1 C14 1.893(4) . ? O1 C12 1.221(4) . ? N1 C2 1.341(5) . ? N1 C1 1.353(4) . ? N2 C11 1.368(4) . ? N2 C10 1.384(4) . ? N2 H2A 0.8800 . ? C1 C11 1.393(5) . ? C1 C12 1.461(5) . ? C2 C3 1.383(5) . ? C2 H2 0.9500 . ? C3 C4 1.372(5) . ? C3 H3 0.9500 . ? C4 C11 1.413(5) . ? C4 C5 1.448(5) . ? C5 C6 1.388(5) . ? C5 C10 1.400(5) . ? C6 C7 1.372(5) . ? C6 H6 0.9500 . ? C7 C8 1.392(5) . ? C7 H7 0.9500 . ? C8 C9 1.374(5) . ? C8 H8 0.9500 . ? C9 C10 1.387(5) . ? C9 H9 0.9500 . ? C12 C13 1.515(5) . ? C13 C18 1.385(5) . ? C13 C14 1.391(5) . ? C14 C15 1.381(5) . ? C15 C16 1.381(5) . ? C15 H15 0.9500 . ? C16 C17 1.380(5) . ? C16 H16 0.9500 . ? C17 C18 1.371(5) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? 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 N1 C1 118.4(3) . . ? C11 N2 C10 108.8(3) . . ? C11 N2 H2A 125.6 . . ? C10 N2 H2A 125.6 . . ? N1 C1 C11 120.7(3) . . ? N1 C1 C12 117.8(4) . . ? C11 C1 C12 121.5(4) . . ? N1 C2 C3 124.1(4) . . ? N1 C2 H2 118.0 . . ? C3 C2 H2 118.0 . . ? C4 C3 C2 118.6(4) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? C3 C4 C11 118.2(4) . . ? C3 C4 C5 134.9(4) . . ? C11 C4 C5 106.9(3) . . ? C6 C5 C10 119.9(4) . . ? C6 C5 C4 134.3(4) . . ? C10 C5 C4 105.7(3) . . ? C7 C6 C5 118.0(4) . . ? C7 C6 H6 121.0 . . ? C5 C6 H6 121.0 . . ? C6 C7 C8 121.5(4) . . ? C6 C7 H7 119.2 . . ? C8 C7 H7 119.2 . . ? C9 C8 C7 121.6(4) . . ? C9 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? C8 C9 C10 116.9(4) . . ? C8 C9 H9 121.5 . . ? C10 C9 H9 121.5 . . ? N2 C10 C9 128.3(4) . . ? N2 C10 C5 109.7(3) . . ? C9 C10 C5 122.0(4) . . ? N2 C11 C1 131.2(3) . . ? N2 C11 C4 108.8(3) . . ? C1 C11 C4 120.0(3) . . ? O1 C12 C1 121.0(4) . . ? O1 C12 C13 119.0(3) . . ? C1 C12 C13 119.9(4) . . ? C18 C13 C14 117.9(3) . . ? C18 C13 C12 118.0(3) . . ? C14 C13 C12 124.0(4) . . ? C15 C14 C13 121.1(4) . . ? C15 C14 Br1 117.7(3) . . ? C13 C14 Br1 121.2(3) . . ? C14 C15 C16 119.8(4) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C17 C16 C15 119.6(4) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C18 C17 C16 120.2(4) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C17 C18 C13 121.4(4) . . ? C17 C18 H18 119.3 . . ? C13 C18 H18 119.3 . . ? 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 C2 N1 C1 C11 -0.9(6) . . . . ? C2 N1 C1 C12 179.9(4) . . . . ? C1 N1 C2 C3 -0.9(6) . . . . ? N1 C2 C3 C4 1.4(6) . . . . ? C2 C3 C4 C11 0.0(5) . . . . ? C2 C3 C4 C5 179.1(4) . . . . ? C3 C4 C5 C6 3.0(8) . . . . ? C11 C4 C5 C6 -177.8(4) . . . . ? C3 C4 C5 C10 -178.6(4) . . . . ? C11 C4 C5 C10 0.7(4) . . . . ? C10 C5 C6 C7 -0.6(6) . . . . ? C4 C5 C6 C7 177.7(4) . . . . ? C5 C6 C7 C8 2.1(6) . . . . ? C6 C7 C8 C9 -2.0(6) . . . . ? C7 C8 C9 C10 0.2(6) . . . . ? C11 N2 C10 C9 179.5(4) . . . . ? C11 N2 C10 C5 0.3(4) . . . . ? C8 C9 C10 N2 -177.8(4) . . . . ? C8 C9 C10 C5 1.4(6) . . . . ? C6 C5 C10 N2 178.1(3) . . . . ? C4 C5 C10 N2 -0.6(4) . . . . ? C6 C5 C10 C9 -1.2(6) . . . . ? C4 C5 C10 C9 -179.9(3) . . . . ? C10 N2 C11 C1 -179.2(4) . . . . ? C10 N2 C11 C4 0.1(4) . . . . ? N1 C1 C11 N2 -178.5(4) . . . . ? C12 C1 C11 N2 0.6(6) . . . . ? N1 C1 C11 C4 2.2(6) . . . . ? C12 C1 C11 C4 -178.7(3) . . . . ? C3 C4 C11 N2 178.9(3) . . . . ? C5 C4 C11 N2 -0.5(4) . . . . ? C3 C4 C11 C1 -1.7(5) . . . . ? C5 C4 C11 C1 178.9(3) . . . . ? N1 C1 C12 O1 175.0(4) . . . . ? C11 C1 C12 O1 -4.1(6) . . . . ? N1 C1 C12 C13 -2.9(5) . . . . ? C11 C1 C12 C13 178.0(4) . . . . ? O1 C12 C13 C18 -62.2(5) . . . . ? C1 C12 C13 C18 115.7(4) . . . . ? O1 C12 C13 C14 114.0(5) . . . . ? C1 C12 C13 C14 -68.1(5) . . . . ? C18 C13 C14 C15 1.5(6) . . . . ? C12 C13 C14 C15 -174.7(4) . . . . ? C18 C13 C14 Br1 178.1(3) . . . . ? C12 C13 C14 Br1 1.9(5) . . . . ? C13 C14 C15 C16 -1.8(6) . . . . ? Br1 C14 C15 C16 -178.5(3) . . . . ? C14 C15 C16 C17 0.9(6) . . . . ? C15 C16 C17 C18 0.3(6) . . . . ? C16 C17 C18 C13 -0.6(6) . . . . ? C14 C13 C18 C17 -0.3(6) . . . . ? C12 C13 C18 C17 176.2(4) . . . . ? 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 N2 H2A O1 0.88 2.34 2.813(4) 114.2 . N2 H2A O1 0.88 2.25 3.013(4) 145.0 5_566 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.555 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.068 data_05135a _database_code_depnum_ccdc_archive 'CCDC 621743' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H11 F N2 O' _chemical_formula_weight 290.29 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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.6767(12) _cell_length_b 7.7705(11) _cell_length_c 19.715(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.173(3) _cell_angle_gamma 90.00 _cell_volume 1329.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1020 _cell_measurement_theta_min 2.348 _cell_measurement_theta_max 22.122 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.451 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9282 _diffrn_reflns_av_R_equivalents 0.0845 _diffrn_reflns_av_sigmaI/netI 0.0784 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2343 _reflns_number_gt 1621 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; There is the presence of intramolecular hydrogen bonding; Hydrogen bonds with H..A < r(A) + 2.000 Angstroms and 110 deg. D-H d(D-H) d(H..A) 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^)+(0.1050P)^2^+0.0694P] 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 constrained _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2343 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1018 _refine_ls_R_factor_gt 0.0672 _refine_ls_wR_factor_ref 0.1905 _refine_ls_wR_factor_gt 0.1715 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 C4 C 0.2435(4) 1.0073(4) 0.49128(16) 0.0237(8) Uani 1 1 d . . . N1 N 0.3886(3) 0.8458(3) 0.60136(14) 0.0261(7) Uani 1 1 d . . . N2 N 0.1074(3) 0.7706(3) 0.46043(13) 0.0259(7) Uani 1 1 d . . . H2A H 0.0701 0.6653 0.4600 0.031 Uiso 1 1 calc R . . O1 O 0.1484(3) 0.4967(3) 0.55821(13) 0.0350(7) Uani 1 1 d . . . F1 F 0.5744(3) 0.5215(3) 0.56199(11) 0.0490(7) Uani 1 1 d . . . C1 C 0.2876(4) 0.7562(4) 0.56257(16) 0.0233(8) Uani 1 1 d . . . C2 C 0.4129(4) 1.0105(4) 0.58732(17) 0.0266(8) Uani 1 1 d . . . H2 H 0.4812 1.0728 0.6165 0.032 Uiso 1 1 calc R . . C3 C 0.3461(4) 1.0975(4) 0.53345(18) 0.0281(8) Uani 1 1 d . . . H3 H 0.3692 1.2151 0.5253 0.034 Uiso 1 1 calc R . . C5 C 0.1531(4) 1.0491(4) 0.43105(17) 0.0240(8) Uani 1 1 d . . . C6 C 0.1347(4) 1.1958(5) 0.39137(18) 0.0320(9) Uani 1 1 d . . . H6 H 0.1899 1.2981 0.4023 0.038 Uiso 1 1 calc R . . C7 C 0.0357(4) 1.1908(5) 0.33614(19) 0.0348(9) Uani 1 1 d . . . H7 H 0.0227 1.2903 0.3086 0.042 Uiso 1 1 calc R . . C8 C -0.0464(4) 1.0404(5) 0.31995(19) 0.0371(10) Uani 1 1 d . . . H8 H -0.1147 1.0401 0.2817 0.045 Uiso 1 1 calc R . . C9 C -0.0303(4) 0.8924(5) 0.35850(18) 0.0310(9) Uani 1 1 d . . . H9 H -0.0858 0.7905 0.3474 0.037 Uiso 1 1 calc R . . C10 C 0.0699(4) 0.8989(4) 0.41384(17) 0.0242(8) Uani 1 1 d . . . C11 C 0.2114(4) 0.8339(4) 0.50697(16) 0.0221(8) Uani 1 1 d . . . C12 C 0.2582(4) 0.5770(4) 0.58201(17) 0.0253(8) Uani 1 1 d . . . C13 C 0.3656(4) 0.4965(4) 0.63385(17) 0.0255(8) Uani 1 1 d . . . C14 C 0.5198(4) 0.4727(4) 0.62223(17) 0.0284(8) Uani 1 1 d . . . C15 C 0.6189(4) 0.3971(4) 0.66834(19) 0.0345(9) Uani 1 1 d . . . H15 H 0.7242 0.3798 0.6579 0.041 Uiso 1 1 calc R . . C16 C 0.5630(5) 0.3469(5) 0.72991(19) 0.0374(10) Uani 1 1 d . . . H16 H 0.6306 0.2968 0.7629 0.045 Uiso 1 1 calc R . . C17 C 0.4097(5) 0.3686(5) 0.74419(19) 0.0370(10) Uani 1 1 d . . . H17 H 0.3719 0.3327 0.7868 0.044 Uiso 1 1 calc R . . C18 C 0.3095(5) 0.4430(4) 0.69637(18) 0.0326(9) Uani 1 1 d . . . H18 H 0.2036 0.4572 0.7062 0.039 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 C4 0.0228(18) 0.0220(18) 0.0264(18) -0.0023(14) 0.0049(15) 0.0002(14) N1 0.0277(16) 0.0265(16) 0.0239(15) -0.0037(13) -0.0029(12) -0.0041(12) N2 0.0278(16) 0.0221(15) 0.0275(16) -0.0001(12) -0.0048(13) -0.0038(12) O1 0.0336(15) 0.0277(14) 0.0432(16) 0.0012(12) -0.0124(12) -0.0072(11) F1 0.0472(15) 0.0595(15) 0.0405(14) 0.0048(12) 0.0043(11) 0.0007(12) C1 0.0207(18) 0.0243(18) 0.0249(18) -0.0007(14) 0.0014(14) -0.0009(14) C2 0.0271(19) 0.0260(18) 0.0267(19) -0.0046(15) -0.0023(15) -0.0037(15) C3 0.0281(19) 0.0206(18) 0.036(2) -0.0029(15) 0.0027(16) -0.0043(15) C5 0.0208(17) 0.0266(18) 0.0249(18) -0.0018(14) 0.0041(14) 0.0032(14) C6 0.030(2) 0.030(2) 0.036(2) 0.0051(16) 0.0041(17) 0.0018(16) C7 0.035(2) 0.036(2) 0.033(2) 0.0096(17) 0.0011(17) 0.0093(17) C8 0.031(2) 0.050(2) 0.030(2) 0.0007(18) -0.0041(17) 0.0088(18) C9 0.028(2) 0.035(2) 0.031(2) -0.0009(16) -0.0024(16) -0.0003(16) C10 0.0200(17) 0.0273(18) 0.0255(19) -0.0007(15) 0.0027(14) 0.0003(14) C11 0.0193(17) 0.0264(18) 0.0206(17) -0.0039(14) 0.0011(14) 0.0006(14) C12 0.0254(19) 0.0290(19) 0.0216(18) -0.0016(14) -0.0017(15) -0.0018(15) C13 0.0302(19) 0.0189(17) 0.0271(19) -0.0031(14) -0.0060(15) -0.0057(14) C14 0.039(2) 0.0246(18) 0.0210(19) 0.0032(15) -0.0036(16) -0.0062(15) C15 0.036(2) 0.029(2) 0.038(2) 0.0030(17) -0.0086(18) -0.0023(17) C16 0.046(2) 0.029(2) 0.036(2) 0.0058(17) -0.0184(19) -0.0032(17) C17 0.050(3) 0.034(2) 0.027(2) 0.0043(17) -0.0078(18) -0.0110(18) C18 0.045(2) 0.0269(19) 0.026(2) 0.0002(15) -0.0051(17) -0.0087(17) _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 C4 C3 1.394(5) . ? C4 C11 1.412(5) . ? C4 C5 1.447(5) . ? N1 C2 1.327(4) . ? N1 C1 1.345(4) . ? N2 C11 1.365(4) . ? N2 C10 1.390(4) . ? N2 H2A 0.8800 . ? O1 C12 1.225(4) . ? F1 C14 1.342(4) . ? C1 C11 1.405(4) . ? C1 C12 1.468(5) . ? C2 C3 1.377(5) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C5 C6 1.390(5) . ? C5 C10 1.410(5) . ? C6 C7 1.374(5) . ? C6 H6 0.9500 . ? C7 C8 1.402(5) . ? C7 H7 0.9500 . ? C8 C9 1.384(5) . ? C8 H8 0.9500 . ? C9 C10 1.382(5) . ? C9 H9 0.9500 . ? C12 C13 1.505(5) . ? C13 C14 1.375(5) . ? C13 C18 1.398(5) . ? C14 C15 1.371(5) . ? C15 C16 1.373(5) . ? C15 H15 0.9500 . ? C16 C17 1.376(5) . ? C16 H16 0.9500 . ? C17 C18 1.395(5) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? 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 C3 C4 C11 118.4(3) . . ? C3 C4 C5 134.9(3) . . ? C11 C4 C5 106.7(3) . . ? C2 N1 C1 119.0(3) . . ? C11 N2 C10 109.2(3) . . ? C11 N2 H2A 125.4 . . ? C10 N2 H2A 125.4 . . ? N1 C1 C11 120.8(3) . . ? N1 C1 C12 117.2(3) . . ? C11 C1 C12 122.0(3) . . ? N1 C2 C3 124.6(3) . . ? N1 C2 H2 117.7 . . ? C3 C2 H2 117.7 . . ? C2 C3 C4 117.8(3) . . ? C2 C3 H3 121.1 . . ? C4 C3 H3 121.1 . . ? C6 C5 C10 119.4(3) . . ? C6 C5 C4 134.4(3) . . ? C10 C5 C4 106.2(3) . . ? C7 C6 C5 119.1(3) . . ? C7 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? C6 C7 C8 120.7(3) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C9 C8 C7 121.5(3) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C10 C9 C8 117.2(3) . . ? C10 C9 H9 121.4 . . ? C8 C9 H9 121.4 . . ? C9 C10 N2 129.1(3) . . ? C9 C10 C5 122.1(3) . . ? N2 C10 C5 108.9(3) . . ? N2 C11 C1 131.6(3) . . ? N2 C11 C4 109.1(3) . . ? C1 C11 C4 119.3(3) . . ? O1 C12 C1 121.4(3) . . ? O1 C12 C13 120.9(3) . . ? C1 C12 C13 117.6(3) . . ? C14 C13 C18 117.7(3) . . ? C14 C13 C12 122.3(3) . . ? C18 C13 C12 120.1(3) . . ? F1 C14 C15 118.7(3) . . ? F1 C14 C13 118.2(3) . . ? C15 C14 C13 123.2(3) . . ? C14 C15 C16 118.7(4) . . ? C14 C15 H15 120.7 . . ? C16 C15 H15 120.7 . . ? C15 C16 C17 120.5(3) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C16 C17 C18 120.3(4) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C17 C18 C13 119.8(4) . . ? C17 C18 H18 120.1 . . ? C13 C18 H18 120.1 . . ? 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 C2 N1 C1 C11 1.5(5) . . . . ? C2 N1 C1 C12 -176.9(3) . . . . ? C1 N1 C2 C3 -2.7(5) . . . . ? N1 C2 C3 C4 1.2(5) . . . . ? C11 C4 C3 C2 1.4(5) . . . . ? C5 C4 C3 C2 -179.3(3) . . . . ? C3 C4 C5 C6 0.8(7) . . . . ? C11 C4 C5 C6 -179.9(4) . . . . ? C3 C4 C5 C10 -178.9(4) . . . . ? C11 C4 C5 C10 0.5(3) . . . . ? C10 C5 C6 C7 0.0(5) . . . . ? C4 C5 C6 C7 -179.6(4) . . . . ? C5 C6 C7 C8 0.3(5) . . . . ? C6 C7 C8 C9 -0.3(6) . . . . ? C7 C8 C9 C10 0.2(5) . . . . ? C8 C9 C10 N2 -179.9(3) . . . . ? C8 C9 C10 C5 0.0(5) . . . . ? C11 N2 C10 C9 -179.8(3) . . . . ? C11 N2 C10 C5 0.2(4) . . . . ? C6 C5 C10 C9 -0.1(5) . . . . ? C4 C5 C10 C9 179.6(3) . . . . ? C6 C5 C10 N2 179.9(3) . . . . ? C4 C5 C10 N2 -0.4(4) . . . . ? C10 N2 C11 C1 -178.1(3) . . . . ? C10 N2 C11 C4 0.2(4) . . . . ? N1 C1 C11 N2 179.1(3) . . . . ? C12 C1 C11 N2 -2.5(5) . . . . ? N1 C1 C11 C4 1.0(5) . . . . ? C12 C1 C11 C4 179.3(3) . . . . ? C3 C4 C11 N2 179.1(3) . . . . ? C5 C4 C11 N2 -0.4(4) . . . . ? C3 C4 C11 C1 -2.4(5) . . . . ? C5 C4 C11 C1 178.1(3) . . . . ? N1 C1 C12 O1 165.9(3) . . . . ? C11 C1 C12 O1 -12.6(5) . . . . ? N1 C1 C12 C13 -12.5(4) . . . . ? C11 C1 C12 C13 169.1(3) . . . . ? O1 C12 C13 C14 118.4(4) . . . . ? C1 C12 C13 C14 -63.2(4) . . . . ? O1 C12 C13 C18 -61.5(5) . . . . ? C1 C12 C13 C18 116.8(3) . . . . ? C18 C13 C14 F1 179.1(3) . . . . ? C12 C13 C14 F1 -0.9(5) . . . . ? C18 C13 C14 C15 1.0(5) . . . . ? C12 C13 C14 C15 -178.9(3) . . . . ? F1 C14 C15 C16 -179.9(3) . . . . ? C13 C14 C15 C16 -1.8(5) . . . . ? C14 C15 C16 C17 1.5(5) . . . . ? C15 C16 C17 C18 -0.4(5) . . . . ? C16 C17 C18 C13 -0.4(5) . . . . ? C14 C13 C18 C17 0.1(5) . . . . ? C12 C13 C18 C17 -180.0(3) . . . . ? 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 N2 H2A O1 0.88 2.30 3.056(4) 144.4 3_566 N2 H2A O1 0.88 2.42 2.889(4) 113.4 . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.287 _refine_diff_density_min -0.377 _refine_diff_density_rms 0.068 data_05136 _database_code_depnum_ccdc_archive 'CCDC 621744' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H11 Cl N2 O' _chemical_formula_weight 306.74 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 0.0000 0.0000 '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 0.0060 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.605(2) _cell_length_b 14.272(4) _cell_length_c 26.587(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2885.6(13) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 564 _cell_measurement_theta_min 2.855 _cell_measurement_theta_max 19.869 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.412 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.267 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19314 _diffrn_reflns_av_R_equivalents 0.2061 _diffrn_reflns_av_sigmaI/netI 0.1614 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2525 _reflns_number_gt 1156 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; The data is poor due to crystal quality. There is intramolecular hydrogen bonding; Hydrogen bonds with H..A < r(A) + 2.000 Angstroms and 110 deg. D-H d(D-H) d(H..A) 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^)+(0.0080P)^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 constrained _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2525 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2187 _refine_ls_R_factor_gt 0.0895 _refine_ls_wR_factor_ref 0.1086 _refine_ls_wR_factor_gt 0.0811 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 N1 N 0.3575(6) 0.0332(3) 0.35391(16) 0.0430(14) Uani 1 1 d . . . O1 O 0.0054(5) -0.0197(2) 0.43528(12) 0.0494(11) Uani 1 1 d . . . Cl1 Cl 0.0002(2) 0.13125(10) 0.31101(5) 0.0616(5) Uani 1 1 d . . . C1 C 0.2651(7) 0.0304(4) 0.3971(2) 0.0376(15) Uani 1 1 d . . . C2 C 0.5210(8) 0.0689(4) 0.3544(2) 0.0509(17) Uani 1 1 d . . . H2 H 0.5871 0.0673 0.3241 0.061 Uiso 1 1 calc R . . C3 C 0.5989(7) 0.1080(4) 0.3968(2) 0.0444(16) Uani 1 1 d . . . H3 H 0.7133 0.1346 0.3952 0.053 Uiso 1 1 calc R . . C4 C 0.5057(8) 0.1072(3) 0.4413(2) 0.0366(14) Uani 1 1 d . . . C5 C 0.5416(7) 0.1386(4) 0.4916(2) 0.0361(15) Uani 1 1 d . . . C6 C 0.6806(8) 0.1839(4) 0.5143(2) 0.0503(18) Uani 1 1 d . . . H6 H 0.7831 0.1996 0.4956 0.060 Uiso 1 1 calc R . . C7 C 0.6677(9) 0.2060(4) 0.5645(3) 0.057(2) Uani 1 1 d . . . H7 H 0.7607 0.2394 0.5803 0.069 Uiso 1 1 calc R . . C8 C 0.5229(9) 0.1807(4) 0.5924(2) 0.0538(18) Uani 1 1 d . . . H8 H 0.5201 0.1955 0.6272 0.065 Uiso 1 1 calc R . . C9 C 0.3820(7) 0.1346(4) 0.5713(2) 0.0397(15) Uani 1 1 d . . . H9 H 0.2819 0.1169 0.5904 0.048 Uiso 1 1 calc R . . C10 C 0.3956(7) 0.1156(4) 0.5204(2) 0.0320(14) Uani 1 1 d . . . C11 C 0.3376(7) 0.0669(4) 0.4415(2) 0.0335(14) Uani 1 1 d . . . C12 C 0.0891(8) -0.0100(4) 0.3964(2) 0.0402(16) Uani 1 1 d . . . C13 C 0.0184(7) -0.0461(4) 0.34674(19) 0.0364(15) Uani 1 1 d . . . C14 C -0.0291(7) 0.0105(4) 0.3074(2) 0.0445(16) Uani 1 1 d . . . C15 C -0.1099(8) -0.0246(5) 0.2646(2) 0.0527(19) Uani 1 1 d . . . H15 H -0.1440 0.0161 0.2380 0.063 Uiso 1 1 calc R . . C16 C -0.1391(8) -0.1190(5) 0.2614(2) 0.062(2) Uani 1 1 d . . . H16 H -0.1936 -0.1441 0.2322 0.074 Uiso 1 1 calc R . . C17 C -0.0912(7) -0.1778(4) 0.2997(2) 0.0535(19) Uani 1 1 d . . . H17 H -0.1089 -0.2435 0.2967 0.064 Uiso 1 1 calc R . . C18 C -0.0174(8) -0.1410(4) 0.3424(2) 0.0507(16) Uani 1 1 d . . . H18 H 0.0099 -0.1815 0.3697 0.061 Uiso 1 1 calc R . . N2 N 0.2710(5) 0.0723(3) 0.48954(16) 0.0318(11) Uani 1 1 d . . . H2A H 0.1672 0.0518 0.4992 0.038 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 N1 0.036(3) 0.058(4) 0.035(3) 0.005(3) 0.009(3) 0.007(3) O1 0.044(3) 0.076(3) 0.029(2) -0.001(2) 0.007(2) -0.010(3) Cl1 0.0658(10) 0.0602(10) 0.0588(10) 0.0109(9) -0.0003(11) 0.0065(11) C1 0.040(4) 0.036(4) 0.037(4) 0.001(3) 0.000(3) 0.001(3) C2 0.037(4) 0.071(5) 0.045(4) 0.010(4) 0.011(4) 0.005(4) C3 0.038(4) 0.046(4) 0.050(4) 0.016(4) 0.003(4) -0.003(3) C4 0.037(4) 0.033(3) 0.040(4) 0.012(3) -0.005(4) -0.005(4) C5 0.026(4) 0.035(4) 0.047(4) 0.010(3) -0.011(3) -0.005(3) C6 0.045(4) 0.042(4) 0.064(5) 0.013(4) -0.010(4) -0.015(3) C7 0.064(5) 0.038(4) 0.069(5) 0.006(4) -0.027(4) -0.018(4) C8 0.069(5) 0.042(4) 0.050(4) 0.000(3) -0.015(4) -0.012(4) C9 0.053(4) 0.030(4) 0.037(4) 0.005(3) 0.000(3) -0.001(3) C10 0.035(4) 0.030(4) 0.032(4) 0.000(3) -0.007(3) -0.001(3) C11 0.038(4) 0.033(4) 0.029(4) 0.003(3) 0.004(3) -0.002(3) C12 0.042(4) 0.045(4) 0.034(4) -0.001(3) -0.009(3) 0.002(3) C13 0.030(4) 0.046(4) 0.032(3) 0.001(3) 0.002(3) 0.003(3) C14 0.039(4) 0.058(4) 0.037(4) 0.003(3) 0.001(3) 0.008(4) C15 0.041(4) 0.088(6) 0.029(4) 0.013(4) -0.002(3) -0.002(4) C16 0.056(5) 0.096(6) 0.033(4) -0.013(5) -0.015(4) -0.003(5) C17 0.046(4) 0.065(5) 0.050(5) -0.015(4) -0.005(4) -0.009(4) C18 0.054(4) 0.059(4) 0.039(4) 0.004(4) -0.005(4) -0.005(4) N2 0.025(3) 0.035(3) 0.036(3) 0.007(3) 0.000(2) -0.003(2) _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 N1 C2 1.344(6) . ? N1 C1 1.348(6) . ? O1 C12 1.222(6) . ? Cl1 C14 1.740(5) . ? C1 C11 1.402(7) . ? C1 C12 1.457(6) . ? C2 C3 1.390(6) . ? C2 H2 0.9500 . ? C3 C4 1.378(6) . ? C3 H3 0.9500 . ? C4 C11 1.402(6) . ? C4 C5 1.437(6) . ? C5 C6 1.379(6) . ? C5 C10 1.388(6) . ? C6 C7 1.376(7) . ? C6 H6 0.9500 . ? C7 C8 1.375(7) . ? C7 H7 0.9500 . ? C8 C9 1.377(6) . ? C8 H8 0.9500 . ? C9 C10 1.384(6) . ? C9 H9 0.9500 . ? C10 N2 1.398(6) . ? C11 N2 1.376(6) . ? C12 C13 1.516(6) . ? C13 C14 1.369(6) . ? C13 C18 1.386(6) . ? C14 C15 1.388(7) . ? C15 C16 1.369(7) . ? C15 H15 0.9500 . ? C16 C17 1.369(7) . ? C16 H16 0.9500 . ? C17 C18 1.371(6) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? N2 H2A 0.8800 . ? 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 N1 C1 119.0(5) . . ? N1 C1 C11 120.1(5) . . ? N1 C1 C12 118.6(6) . . ? C11 C1 C12 121.3(5) . . ? N1 C2 C3 123.7(5) . . ? N1 C2 H2 118.2 . . ? C3 C2 H2 118.2 . . ? C4 C3 C2 118.3(5) . . ? C4 C3 H3 120.9 . . ? C2 C3 H3 120.9 . . ? C3 C4 C11 118.4(5) . . ? C3 C4 C5 134.3(6) . . ? C11 C4 C5 107.2(5) . . ? C6 C5 C10 118.8(5) . . ? C6 C5 C4 134.4(6) . . ? C10 C5 C4 106.8(5) . . ? C7 C6 C5 118.5(6) . . ? C7 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? C8 C7 C6 121.4(6) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C7 C8 C9 121.9(6) . . ? C7 C8 H8 119.1 . . ? C9 C8 H8 119.1 . . ? C8 C9 C10 115.7(6) . . ? C8 C9 H9 122.1 . . ? C10 C9 H9 122.1 . . ? C9 C10 C5 123.6(5) . . ? C9 C10 N2 127.5(5) . . ? C5 C10 N2 108.8(5) . . ? N2 C11 C4 108.5(5) . . ? N2 C11 C1 131.1(5) . . ? C4 C11 C1 120.4(5) . . ? O1 C12 C1 120.8(5) . . ? O1 C12 C13 120.9(5) . . ? C1 C12 C13 118.2(5) . . ? C14 C13 C18 117.5(5) . . ? C14 C13 C12 123.9(5) . . ? C18 C13 C12 118.3(5) . . ? C13 C14 C15 122.0(6) . . ? C13 C14 Cl1 120.6(5) . . ? C15 C14 Cl1 117.3(5) . . ? C16 C15 C14 118.5(6) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? C15 C16 C17 121.0(6) . . ? C15 C16 H16 119.5 . . ? C17 C16 H16 119.5 . . ? C16 C17 C18 119.3(6) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C17 C18 C13 121.5(6) . . ? C17 C18 H18 119.2 . . ? C13 C18 H18 119.2 . . ? C11 N2 C10 108.6(4) . . ? C11 N2 H2A 125.7 . . ? C10 N2 H2A 125.7 . . ? 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 C2 N1 C1 C11 1.8(8) . . . . ? C2 N1 C1 C12 -179.0(5) . . . . ? C1 N1 C2 C3 -3.4(8) . . . . ? N1 C2 C3 C4 2.3(8) . . . . ? C2 C3 C4 C11 0.2(8) . . . . ? C2 C3 C4 C5 178.9(5) . . . . ? C3 C4 C5 C6 2.3(11) . . . . ? C11 C4 C5 C6 -178.8(6) . . . . ? C3 C4 C5 C10 -178.4(6) . . . . ? C11 C4 C5 C10 0.5(6) . . . . ? C10 C5 C6 C7 -1.1(8) . . . . ? C4 C5 C6 C7 178.2(6) . . . . ? C5 C6 C7 C8 2.4(9) . . . . ? C6 C7 C8 C9 -1.9(10) . . . . ? C7 C8 C9 C10 -0.1(9) . . . . ? C8 C9 C10 C5 1.5(8) . . . . ? C8 C9 C10 N2 -178.2(5) . . . . ? C6 C5 C10 C9 -0.9(8) . . . . ? C4 C5 C10 C9 179.6(5) . . . . ? C6 C5 C10 N2 178.8(4) . . . . ? C4 C5 C10 N2 -0.6(6) . . . . ? C3 C4 C11 N2 178.9(4) . . . . ? C5 C4 C11 N2 -0.2(6) . . . . ? C3 C4 C11 C1 -1.5(8) . . . . ? C5 C4 C11 C1 179.4(5) . . . . ? N1 C1 C11 N2 180.0(5) . . . . ? C12 C1 C11 N2 0.8(9) . . . . ? N1 C1 C11 C4 0.6(8) . . . . ? C12 C1 C11 C4 -178.6(5) . . . . ? N1 C1 C12 O1 175.0(5) . . . . ? C11 C1 C12 O1 -5.8(8) . . . . ? N1 C1 C12 C13 -0.5(8) . . . . ? C11 C1 C12 C13 178.7(5) . . . . ? O1 C12 C13 C14 113.9(7) . . . . ? C1 C12 C13 C14 -70.6(7) . . . . ? O1 C12 C13 C18 -59.2(8) . . . . ? C1 C12 C13 C18 116.3(6) . . . . ? C18 C13 C14 C15 -0.1(9) . . . . ? C12 C13 C14 C15 -173.3(6) . . . . ? C18 C13 C14 Cl1 176.6(4) . . . . ? C12 C13 C14 Cl1 3.4(8) . . . . ? C13 C14 C15 C16 -1.4(9) . . . . ? Cl1 C14 C15 C16 -178.1(5) . . . . ? C14 C15 C16 C17 0.4(10) . . . . ? C15 C16 C17 C18 1.9(10) . . . . ? C16 C17 C18 C13 -3.4(9) . . . . ? C14 C13 C18 C17 2.5(9) . . . . ? C12 C13 C18 C17 176.1(5) . . . . ? C4 C11 N2 C10 -0.2(6) . . . . ? C1 C11 N2 C10 -179.7(6) . . . . ? C9 C10 N2 C11 -179.7(5) . . . . ? C5 C10 N2 C11 0.5(6) . . . . ? 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 N2 H2A O1 0.88 2.23 2.996(5) 145.6 5_556 N2 H2A O1 0.88 2.33 2.808(5) 113.9 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.180 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.047 data_06004a _database_code_depnum_ccdc_archive 'CCDC 621745' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H13 Br N2 O' _chemical_formula_weight 353.21 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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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 23.342(4) _cell_length_b 7.5017(14) _cell_length_c 17.360(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.055(3) _cell_angle_gamma 90.00 _cell_volume 2961.3(9) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 834 _cell_measurement_theta_min 2.860 _cell_measurement_theta_max 24.147 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.585 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 2.779 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.516 _exptl_absorpt_correction_T_max 0.862 _exptl_absorpt_process_details ; absorption correction based on 5653 reflections(SADABS);Rint 0.0780 before correction and 0.0433 after. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10329 _diffrn_reflns_av_R_equivalents 0.0481 _diffrn_reflns_av_sigmaI/netI 0.0422 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2606 _reflns_number_gt 2087 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; There is the presence of hydrogen bonding: Hydrogen bonds with H..A < r(A) + 2.000 Angstroms and 110 deg. D-H d(D-H) d(H..A) 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^)+(0.0557P)^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 constrained _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2606 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0458 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0916 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 0.964 _refine_ls_restrained_S_all 0.964 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 Br1 Br 0.419628(14) 0.39794(4) 0.215749(19) 0.04218(15) Uani 1 1 d . . . O1 O 0.43331(9) 0.4378(3) 0.45098(13) 0.0393(5) Uani 1 1 d . . . N1 N 0.39245(11) 0.0689(3) 0.33398(16) 0.0339(6) Uani 1 1 d . . . N2 N 0.53762(10) 0.2226(3) 0.44710(14) 0.0314(6) Uani 1 1 d . . . H2 H 0.5342 0.3232 0.4659 0.036(9) Uiso 1 1 d R . . C1 C 0.43070(12) 0.1720(4) 0.37693(16) 0.0264(6) Uani 1 1 d . . . C2 C 0.41283(17) -0.1032(5) 0.3116(3) 0.0735(15) Uani 1 1 d . . . H2A H 0.3834 -0.1924 0.3195 0.088 Uiso 1 1 calc R . . H2B H 0.4104 -0.0976 0.2540 0.088 Uiso 1 1 calc R . . C3 C 0.46896(15) -0.1754(5) 0.3465(2) 0.0577(11) Uani 1 1 d . . . H3A H 0.4855 -0.2308 0.3046 0.069 Uiso 1 1 calc R . . H3B H 0.4640 -0.2706 0.3840 0.069 Uiso 1 1 calc R . . C4 C 0.51170(13) -0.0412(4) 0.38950(17) 0.0294(7) Uani 1 1 d . . . C5 C 0.57294(13) -0.0459(4) 0.42197(17) 0.0322(7) Uani 1 1 d . . . C6 C 0.61766(15) -0.1724(5) 0.4239(2) 0.0452(8) Uani 1 1 d . . . H6 H 0.6088 -0.2862 0.4002 0.054 Uiso 1 1 calc R . . C7 C 0.67417(15) -0.1293(5) 0.4605(2) 0.0522(10) Uani 1 1 d . . . H7 H 0.7047 -0.2138 0.4616 0.063 Uiso 1 1 calc R . . C8 C 0.68789(15) 0.0370(5) 0.4964(2) 0.0486(9) Uani 1 1 d . . . H8 H 0.7275 0.0626 0.5218 0.058 Uiso 1 1 calc R . . C9 C 0.64573(14) 0.1633(5) 0.49560(19) 0.0429(8) Uani 1 1 d . . . H9 H 0.6554 0.2761 0.5199 0.052 Uiso 1 1 calc R . . C10 C 0.58811(13) 0.1218(4) 0.45828(17) 0.0315(7) Uani 1 1 d . . . C11 C 0.49147(12) 0.1212(3) 0.40567(16) 0.0254(6) Uani 1 1 d . . . C12 C 0.40871(12) 0.3506(4) 0.39340(18) 0.0288(7) Uani 1 1 d . . . C13 C 0.35470(12) 0.4183(3) 0.33699(19) 0.0301(7) Uani 1 1 d . . . C14 C 0.35217(13) 0.4409(4) 0.25694(19) 0.0321(7) Uani 1 1 d . . . C15 C 0.30168(14) 0.5028(4) 0.2065(2) 0.0444(9) Uani 1 1 d . . . H15 H 0.3009 0.5193 0.1521 0.053 Uiso 1 1 calc R . . C16 C 0.25273(15) 0.5404(5) 0.2347(3) 0.0521(10) Uani 1 1 d . . . H16 H 0.2179 0.5812 0.1997 0.063 Uiso 1 1 calc R . . C17 C 0.25422(14) 0.5190(5) 0.3131(3) 0.0506(10) Uani 1 1 d . . . H17 H 0.2203 0.5457 0.3325 0.061 Uiso 1 1 calc R . . C18 C 0.30462(14) 0.4590(4) 0.3649(2) 0.0397(8) Uani 1 1 d . . . H18 H 0.3051 0.4454 0.4194 0.048 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 Br1 0.0395(2) 0.0486(2) 0.0397(2) 0.00330(15) 0.01176(15) 0.00113(15) O1 0.0343(12) 0.0384(12) 0.0409(13) -0.0151(10) -0.0003(10) -0.0003(10) N1 0.0283(14) 0.0267(14) 0.0424(16) -0.0062(11) -0.0010(12) 0.0000(11) N2 0.0266(13) 0.0288(15) 0.0362(15) -0.0084(11) 0.0015(11) 0.0008(11) C1 0.0236(15) 0.0260(14) 0.0295(16) 0.0006(12) 0.0056(12) -0.0014(12) C2 0.042(2) 0.043(2) 0.117(4) -0.037(2) -0.020(2) 0.0084(18) C3 0.040(2) 0.040(2) 0.083(3) -0.023(2) -0.0075(19) 0.0026(17) C4 0.0274(16) 0.0296(16) 0.0287(17) 0.0000(12) 0.0011(13) 0.0017(13) C5 0.0299(17) 0.0363(17) 0.0282(17) 0.0023(13) 0.0021(13) 0.0054(13) C6 0.038(2) 0.0426(19) 0.052(2) -0.0021(17) 0.0033(16) 0.0101(16) C7 0.0340(19) 0.057(3) 0.061(2) 0.0055(18) 0.0019(17) 0.0181(17) C8 0.0267(18) 0.067(2) 0.047(2) 0.0027(19) -0.0036(15) 0.0035(17) C9 0.0344(19) 0.047(2) 0.042(2) -0.0035(16) -0.0024(15) -0.0050(16) C10 0.0262(16) 0.0392(18) 0.0272(16) 0.0019(13) 0.0021(13) 0.0008(13) C11 0.0251(15) 0.0262(16) 0.0237(14) -0.0002(11) 0.0027(12) -0.0010(12) C12 0.0205(15) 0.0300(16) 0.0366(17) -0.0025(13) 0.0077(13) -0.0038(12) C13 0.0217(15) 0.0209(15) 0.0459(19) -0.0042(13) 0.0040(14) -0.0030(11) C14 0.0255(16) 0.0253(16) 0.0426(19) -0.0001(13) 0.0014(14) -0.0019(12) C15 0.0333(19) 0.041(2) 0.052(2) 0.0094(17) -0.0038(16) -0.0041(16) C16 0.0303(19) 0.0351(19) 0.081(3) 0.0139(19) -0.0078(19) 0.0003(15) C17 0.0258(18) 0.036(2) 0.091(3) -0.0049(19) 0.0142(19) 0.0021(15) C18 0.0312(18) 0.0319(16) 0.057(2) -0.0061(16) 0.0108(16) 0.0008(14) _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 Br1 C14 1.898(3) . ? O1 C12 1.224(3) . ? N1 C1 1.285(4) . ? N1 C2 1.458(4) . ? N2 C10 1.377(4) . ? N2 C11 1.380(4) . ? N2 H2 0.8337 . ? C1 C11 1.444(4) . ? C1 C12 1.486(4) . ? C2 C3 1.421(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.493(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C11 1.359(4) . ? C4 C5 1.414(4) . ? C5 C6 1.406(4) . ? C5 C10 1.416(4) . ? C6 C7 1.367(5) . ? C6 H6 0.9500 . ? C7 C8 1.398(5) . ? C7 H7 0.9500 . ? C8 C9 1.364(5) . ? C8 H8 0.9500 . ? C9 C10 1.390(4) . ? C9 H9 0.9500 . ? C12 C13 1.499(4) . ? C13 C14 1.388(4) . ? C13 C18 1.396(4) . ? C14 C15 1.380(4) . ? C15 C16 1.370(5) . ? C15 H15 0.9500 . ? C16 C17 1.364(5) . ? C16 H16 0.9500 . ? C17 C18 1.384(5) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? 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 C1 N1 C2 117.5(3) . . ? C10 N2 C11 108.3(2) . . ? C10 N2 H2 126.6 . . ? C11 N2 H2 124.8 . . ? N1 C1 C11 122.8(3) . . ? N1 C1 C12 115.5(3) . . ? C11 C1 C12 121.7(2) . . ? C3 C2 N1 123.3(3) . . ? C3 C2 H2A 106.5 . . ? N1 C2 H2A 106.5 . . ? C3 C2 H2B 106.5 . . ? N1 C2 H2B 106.5 . . ? H2A C2 H2B 106.5 . . ? C2 C3 C4 113.8(3) . . ? C2 C3 H3A 108.8 . . ? C4 C3 H3A 108.8 . . ? C2 C3 H3B 108.8 . . ? C4 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? C11 C4 C5 107.9(3) . . ? C11 C4 C3 118.9(3) . . ? C5 C4 C3 133.2(3) . . ? C6 C5 C4 134.8(3) . . ? C6 C5 C10 118.7(3) . . ? C4 C5 C10 106.5(3) . . ? C7 C6 C5 119.0(3) . . ? C7 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? C6 C7 C8 121.2(3) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C9 C8 C7 121.5(3) . . ? C9 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? C8 C9 C10 118.0(3) . . ? C8 C9 H9 121.0 . . ? C10 C9 H9 121.0 . . ? N2 C10 C9 130.6(3) . . ? N2 C10 C5 107.8(2) . . ? C9 C10 C5 121.7(3) . . ? C4 C11 N2 109.6(2) . . ? C4 C11 C1 121.7(3) . . ? N2 C11 C1 128.7(2) . . ? O1 C12 C1 121.4(3) . . ? O1 C12 C13 121.5(3) . . ? C1 C12 C13 117.1(2) . . ? C14 C13 C18 118.1(3) . . ? C14 C13 C12 122.3(3) . . ? C18 C13 C12 119.6(3) . . ? C15 C14 C13 120.9(3) . . ? C15 C14 Br1 118.7(3) . . ? C13 C14 Br1 120.3(2) . . ? C16 C15 C14 120.3(3) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C17 C16 C15 119.8(3) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C18 120.8(3) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C17 C18 C13 120.1(3) . . ? C17 C18 H18 119.9 . . ? C13 C18 H18 119.9 . . ? 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 C2 N1 C1 C11 -2.4(5) . . . . ? C2 N1 C1 C12 175.8(3) . . . . ? C1 N1 C2 C3 12.4(6) . . . . ? N1 C2 C3 C4 -17.4(7) . . . . ? C2 C3 C4 C11 13.4(5) . . . . ? C2 C3 C4 C5 -169.1(4) . . . . ? C11 C4 C5 C6 -178.9(3) . . . . ? C3 C4 C5 C6 3.3(6) . . . . ? C11 C4 C5 C10 0.0(3) . . . . ? C3 C4 C5 C10 -177.7(4) . . . . ? C4 C5 C6 C7 178.7(4) . . . . ? C10 C5 C6 C7 -0.2(5) . . . . ? C5 C6 C7 C8 0.6(6) . . . . ? C6 C7 C8 C9 -0.7(6) . . . . ? C7 C8 C9 C10 0.3(5) . . . . ? C11 N2 C10 C9 179.4(3) . . . . ? C11 N2 C10 C5 0.7(3) . . . . ? C8 C9 C10 N2 -178.5(3) . . . . ? C8 C9 C10 C5 0.1(5) . . . . ? C6 C5 C10 N2 178.7(3) . . . . ? C4 C5 C10 N2 -0.5(3) . . . . ? C6 C5 C10 C9 -0.1(5) . . . . ? C4 C5 C10 C9 -179.3(3) . . . . ? C5 C4 C11 N2 0.4(3) . . . . ? C3 C4 C11 N2 178.5(3) . . . . ? C5 C4 C11 C1 176.9(3) . . . . ? C3 C4 C11 C1 -5.0(4) . . . . ? C10 N2 C11 C4 -0.7(3) . . . . ? C10 N2 C11 C1 -176.8(3) . . . . ? N1 C1 C11 C4 -0.8(5) . . . . ? C12 C1 C11 C4 -179.0(3) . . . . ? N1 C1 C11 N2 174.9(3) . . . . ? C12 C1 C11 N2 -3.2(5) . . . . ? N1 C1 C12 O1 156.8(3) . . . . ? C11 C1 C12 O1 -25.0(4) . . . . ? N1 C1 C12 C13 -22.5(4) . . . . ? C11 C1 C12 C13 155.8(3) . . . . ? O1 C12 C13 C14 121.7(3) . . . . ? C1 C12 C13 C14 -59.0(4) . . . . ? O1 C12 C13 C18 -58.9(4) . . . . ? C1 C12 C13 C18 120.4(3) . . . . ? C18 C13 C14 C15 0.3(4) . . . . ? C12 C13 C14 C15 179.7(3) . . . . ? C18 C13 C14 Br1 177.3(2) . . . . ? C12 C13 C14 Br1 -3.3(4) . . . . ? C13 C14 C15 C16 -1.0(5) . . . . ? Br1 C14 C15 C16 -178.0(2) . . . . ? C14 C15 C16 C17 0.9(5) . . . . ? C15 C16 C17 C18 -0.3(5) . . . . ? C16 C17 C18 C13 -0.4(5) . . . . ? C14 C13 C18 C17 0.4(4) . . . . ? C12 C13 C18 C17 -179.1(3) . . . . ? 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 N2 H2 O1 0.83 2.46 2.935(3) 116.6 . N2 H2 O1 0.83 2.32 3.088(3) 153.8 5_666 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.588 _refine_diff_density_min -0.399 _refine_diff_density_rms 0.072 data_06005 _database_code_depnum_ccdc_archive 'CCDC 621746' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H13 F N2 O' _chemical_formula_weight 292.30 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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.686(3) _cell_length_b 7.3469(16) _cell_length_c 16.098(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.710(4) _cell_angle_gamma 90.00 _cell_volume 1362.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 608 _cell_measurement_theta_min 2.354 _cell_measurement_theta_max 24.306 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.425 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9489 _diffrn_reflns_av_R_equivalents 0.0667 _diffrn_reflns_av_sigmaI/netI 0.0665 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 24.98 _reflns_number_total 2402 _reflns_number_gt 1730 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; There is the presence of intramolecular hydrogen bonding; Hydrogen bonds with H..A < r(A) + 2.000 Angstroms and 110 deg. D-H d(D-H) d(H..A) 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^)+(0.0298P)^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 constrained _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2402 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0689 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.0896 _refine_ls_wR_factor_gt 0.0826 _refine_ls_goodness_of_fit_ref 0.937 _refine_ls_restrained_S_all 0.937 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 F1 F 0.24756(10) 0.49568(15) 1.08811(7) 0.0369(3) Uani 1 1 d . . . O1 O -0.04493(12) 0.2754(2) 0.98358(9) 0.0389(4) Uani 1 1 d . . . N1 N 0.23614(14) 0.1178(2) 1.02732(10) 0.0293(4) Uani 1 1 d . . . N2 N 0.03221(14) 0.2032(2) 0.82894(10) 0.0264(4) Uani 1 1 d . . . H2 H -0.0343 0.2349 0.8445 0.061(8) Uiso 1 1 d R . . C1 C 0.14681(17) 0.1830(3) 0.97882(12) 0.0244(5) Uani 1 1 d . . . C2 C 0.31569(18) 0.0072(3) 0.98688(12) 0.0353(6) Uani 1 1 d . . . H2A H 0.2872 -0.1199 0.9840 0.042 Uiso 1 1 calc R . . H2B H 0.3926 0.0080 1.0237 0.042 Uiso 1 1 calc R . . C3 C 0.33221(17) 0.0639(3) 0.89948(12) 0.0283(5) Uani 1 1 d . . . H3A H 0.3820 0.1736 0.9028 0.034 Uiso 1 1 calc R . . H3B H 0.3709 -0.0350 0.8729 0.034 Uiso 1 1 calc R . . C4 C 0.21696(16) 0.1035(2) 0.84802(12) 0.0235(5) Uani 1 1 d . . . C5 C 0.17350(16) 0.1039(2) 0.76000(12) 0.0230(5) Uani 1 1 d . . . C6 C 0.21996(18) 0.0558(3) 0.68796(12) 0.0265(5) Uani 1 1 d . . . H6 H 0.2983 0.0165 0.6929 0.032 Uiso 1 1 calc R . . C7 C 0.15058(18) 0.0664(3) 0.61041(13) 0.0313(5) Uani 1 1 d . . . H7 H 0.1810 0.0330 0.5615 0.038 Uiso 1 1 calc R . . C8 C 0.03483(18) 0.1262(3) 0.60237(13) 0.0306(5) Uani 1 1 d . . . H8 H -0.0115 0.1318 0.5480 0.037 Uiso 1 1 calc R . . C9 C -0.01266(17) 0.1767(3) 0.67136(12) 0.0276(5) Uani 1 1 d . . . H9 H -0.0907 0.2180 0.6655 0.033 Uiso 1 1 calc R . . C10 C 0.05724(16) 0.1652(3) 0.75005(12) 0.0233(5) Uani 1 1 d . . . C11 C 0.12958(16) 0.1631(3) 0.88793(12) 0.0237(5) Uani 1 1 d . . . C12 C 0.05474(18) 0.2681(3) 1.02105(13) 0.0270(5) Uani 1 1 d . . . C13 C 0.08514(16) 0.3235(3) 1.11094(12) 0.0246(5) Uani 1 1 d . . . C14 C 0.18098(17) 0.4291(3) 1.14249(13) 0.0273(5) Uani 1 1 d . . . C15 C 0.20943(18) 0.4737(3) 1.22600(13) 0.0329(5) Uani 1 1 d . . . H15 H 0.2756 0.5467 1.2456 0.039 Uiso 1 1 calc R . . C16 C 0.13998(19) 0.4106(3) 1.28113(13) 0.0383(6) Uani 1 1 d . . . H16 H 0.1596 0.4379 1.3395 0.046 Uiso 1 1 calc R . . C17 C 0.0421(2) 0.3078(3) 1.25230(13) 0.0368(6) Uani 1 1 d . . . H17 H -0.0057 0.2656 1.2905 0.044 Uiso 1 1 calc R . . C18 C 0.01448(18) 0.2669(3) 1.16714(13) 0.0288(5) Uani 1 1 d . . . H18 H -0.0538 0.1991 1.1470 0.035 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 F1 0.0331(7) 0.0407(7) 0.0388(7) 0.0053(6) 0.0111(6) -0.0032(6) O1 0.0250(9) 0.0596(11) 0.0309(9) -0.0063(8) 0.0016(7) 0.0058(8) N1 0.0291(10) 0.0319(10) 0.0265(10) -0.0018(8) 0.0033(8) 0.0065(8) N2 0.0228(10) 0.0328(10) 0.0236(10) -0.0032(8) 0.0038(8) 0.0016(8) C1 0.0244(11) 0.0245(11) 0.0249(11) -0.0004(9) 0.0060(9) 0.0003(9) C2 0.0321(13) 0.0451(14) 0.0287(13) -0.0013(11) 0.0051(10) 0.0125(11) C3 0.0313(12) 0.0283(12) 0.0261(12) -0.0009(9) 0.0069(10) 0.0048(10) C4 0.0258(11) 0.0194(11) 0.0254(12) 0.0005(9) 0.0046(9) 0.0004(9) C5 0.0301(12) 0.0176(11) 0.0218(11) -0.0013(9) 0.0060(9) -0.0023(9) C6 0.0296(12) 0.0221(11) 0.0286(12) -0.0009(9) 0.0075(10) -0.0001(9) C7 0.0430(14) 0.0274(12) 0.0250(12) -0.0037(10) 0.0102(10) -0.0017(11) C8 0.0400(13) 0.0272(12) 0.0224(12) -0.0036(9) -0.0016(10) -0.0038(10) C9 0.0284(12) 0.0238(11) 0.0293(12) -0.0006(10) 0.0015(10) -0.0014(9) C10 0.0273(12) 0.0211(11) 0.0217(11) -0.0024(9) 0.0045(9) -0.0037(9) C11 0.0239(11) 0.0235(11) 0.0230(11) -0.0003(9) 0.0018(9) -0.0004(9) C12 0.0280(13) 0.0259(12) 0.0274(12) 0.0018(9) 0.0053(10) 0.0003(10) C13 0.0255(12) 0.0243(11) 0.0245(11) -0.0002(9) 0.0053(9) 0.0051(9) C14 0.0270(12) 0.0280(12) 0.0291(12) 0.0024(10) 0.0110(10) 0.0036(9) C15 0.0343(13) 0.0293(13) 0.0330(13) -0.0077(10) -0.0006(11) 0.0015(10) C16 0.0518(16) 0.0390(14) 0.0241(13) -0.0084(11) 0.0063(11) 0.0096(12) C17 0.0453(15) 0.0364(13) 0.0327(14) -0.0007(11) 0.0187(11) 0.0072(11) C18 0.0285(12) 0.0273(12) 0.0320(13) -0.0013(10) 0.0090(10) 0.0031(9) _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 F1 C14 1.357(2) . ? O1 C12 1.219(2) . ? N1 C1 1.286(2) . ? N1 C2 1.467(2) . ? N2 C10 1.379(2) . ? N2 C11 1.385(2) . ? N2 H2 0.8867 . ? C1 C11 1.450(3) . ? C1 C12 1.503(3) . ? C2 C3 1.510(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.486(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C11 1.367(2) . ? C4 C5 1.422(3) . ? C5 C6 1.406(2) . ? C5 C10 1.415(3) . ? C6 C7 1.371(3) . ? C6 H6 0.9500 . ? C7 C8 1.407(3) . ? C7 H7 0.9500 . ? C8 C9 1.374(3) . ? C8 H8 0.9500 . ? C9 C10 1.389(3) . ? C9 H9 0.9500 . ? C12 C13 1.487(3) . ? C13 C14 1.386(3) . ? C13 C18 1.388(3) . ? C14 C15 1.369(3) . ? C15 C16 1.380(3) . ? C15 H15 0.9500 . ? C16 C17 1.383(3) . ? C16 H16 0.9500 . ? C17 C18 1.387(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? 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 C1 N1 C2 116.55(17) . . ? C10 N2 C11 108.13(16) . . ? C10 N2 H2 130.2 . . ? C11 N2 H2 121.3 . . ? N1 C1 C11 122.37(18) . . ? N1 C1 C12 116.76(17) . . ? C11 C1 C12 120.68(18) . . ? N1 C2 C3 116.81(17) . . ? N1 C2 H2A 108.1 . . ? C3 C2 H2A 108.1 . . ? N1 C2 H2B 108.1 . . ? C3 C2 H2B 108.1 . . ? H2A C2 H2B 107.3 . . ? C4 C3 C2 109.08(16) . . ? C4 C3 H3A 109.9 . . ? C2 C3 H3A 109.9 . . ? C4 C3 H3B 109.9 . . ? C2 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? C11 C4 C5 107.34(17) . . ? C11 C4 C3 118.64(17) . . ? C5 C4 C3 133.91(18) . . ? C6 C5 C10 118.93(17) . . ? C6 C5 C4 134.31(19) . . ? C10 C5 C4 106.75(17) . . ? C7 C6 C5 119.03(19) . . ? C7 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? C6 C7 C8 120.87(19) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C9 C8 C7 121.54(19) . . ? C9 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? C8 C9 C10 117.73(19) . . ? C8 C9 H9 121.1 . . ? C10 C9 H9 121.1 . . ? N2 C10 C9 130.10(18) . . ? N2 C10 C5 108.00(16) . . ? C9 C10 C5 121.89(18) . . ? C4 C11 N2 109.77(17) . . ? C4 C11 C1 121.25(18) . . ? N2 C11 C1 128.94(17) . . ? O1 C12 C13 121.39(18) . . ? O1 C12 C1 119.44(18) . . ? C13 C12 C1 118.84(18) . . ? C14 C13 C18 117.51(18) . . ? C14 C13 C12 123.71(18) . . ? C18 C13 C12 118.78(19) . . ? F1 C14 C15 118.46(19) . . ? F1 C14 C13 118.76(18) . . ? C15 C14 C13 122.75(19) . . ? C14 C15 C16 118.6(2) . . ? C14 C15 H15 120.7 . . ? C16 C15 H15 120.7 . . ? C15 C16 C17 120.7(2) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C17 C18 119.4(2) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C17 C18 C13 120.9(2) . . ? C17 C18 H18 119.5 . . ? C13 C18 H18 119.5 . . ? 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 C2 N1 C1 C11 -5.3(3) . . . . ? C2 N1 C1 C12 169.66(17) . . . . ? C1 N1 C2 C3 35.3(3) . . . . ? N1 C2 C3 C4 -45.5(2) . . . . ? C2 C3 C4 C11 28.5(2) . . . . ? C2 C3 C4 C5 -155.9(2) . . . . ? C11 C4 C5 C6 -179.0(2) . . . . ? C3 C4 C5 C6 5.0(4) . . . . ? C11 C4 C5 C10 -0.3(2) . . . . ? C3 C4 C5 C10 -176.2(2) . . . . ? C10 C5 C6 C7 -1.3(3) . . . . ? C4 C5 C6 C7 177.4(2) . . . . ? C5 C6 C7 C8 0.7(3) . . . . ? C6 C7 C8 C9 0.3(3) . . . . ? C7 C8 C9 C10 -0.6(3) . . . . ? C11 N2 C10 C9 177.5(2) . . . . ? C11 N2 C10 C5 -1.2(2) . . . . ? C8 C9 C10 N2 -178.69(19) . . . . ? C8 C9 C10 C5 -0.1(3) . . . . ? C6 C5 C10 N2 179.88(17) . . . . ? C4 C5 C10 N2 0.9(2) . . . . ? C6 C5 C10 C9 1.0(3) . . . . ? C4 C5 C10 C9 -177.98(18) . . . . ? C5 C4 C11 N2 -0.5(2) . . . . ? C3 C4 C11 N2 176.20(16) . . . . ? C5 C4 C11 C1 -178.45(17) . . . . ? C3 C4 C11 C1 -1.8(3) . . . . ? C10 N2 C11 C4 1.1(2) . . . . ? C10 N2 C11 C1 178.84(19) . . . . ? N1 C1 C11 C4 -12.1(3) . . . . ? C12 C1 C11 C4 173.15(18) . . . . ? N1 C1 C11 N2 170.36(19) . . . . ? C12 C1 C11 N2 -4.4(3) . . . . ? N1 C1 C12 O1 -155.07(19) . . . . ? C11 C1 C12 O1 19.9(3) . . . . ? N1 C1 C12 C13 18.4(3) . . . . ? C11 C1 C12 C13 -166.55(18) . . . . ? O1 C12 C13 C14 -136.3(2) . . . . ? C1 C12 C13 C14 50.4(3) . . . . ? O1 C12 C13 C18 43.9(3) . . . . ? C1 C12 C13 C18 -129.5(2) . . . . ? C18 C13 C14 F1 -176.03(16) . . . . ? C12 C13 C14 F1 4.1(3) . . . . ? C18 C13 C14 C15 2.0(3) . . . . ? C12 C13 C14 C15 -177.87(19) . . . . ? F1 C14 C15 C16 178.18(17) . . . . ? C13 C14 C15 C16 0.2(3) . . . . ? C14 C15 C16 C17 -1.5(3) . . . . ? C15 C16 C17 C18 0.6(3) . . . . ? C16 C17 C18 C13 1.7(3) . . . . ? C14 C13 C18 C17 -2.9(3) . . . . ? C12 C13 C18 C17 176.97(18) . . . . ? 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 N2 H2 O1 0.89 2.28 2.837(2) 120.5 . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.185 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.041 data_06011 _database_code_depnum_ccdc_archive 'CCDC 621747' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H12 N2 O' _chemical_formula_weight 272.30 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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.2230(18) _cell_length_b 13.841(4) _cell_length_c 15.692(5) _cell_angle_alpha 92.103(7) _cell_angle_beta 93.903(5) _cell_angle_gamma 102.953(5) _cell_volume 1312.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 726 _cell_measurement_theta_min 2.943 _cell_measurement_theta_max 28.271 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9574 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0676 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4594 _reflns_number_gt 3380 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Intramolecular and intermolecular hydrogen bonding. Hydrogen bonds with H..A < r(A) + 2.000 Angstroms and 110 deg. D-H d(D-H) d(H..A) 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^)+(0.0351P)^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 constrained _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4594 _refine_ls_number_parameters 381 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0758 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1042 _refine_ls_wR_factor_gt 0.0947 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 O1 O 0.3315(2) -0.07534(10) 0.04641(9) 0.0357(4) Uani 1 1 d . . . N1 N -0.1410(3) -0.04576(12) 0.14845(10) 0.0312(4) Uani 1 1 d . . . N2 N 0.3370(3) 0.12320(12) 0.06337(10) 0.0309(4) Uani 1 1 d . . . H1 H 0.4129 0.0922 0.0379 0.035(6) Uiso 1 1 d R . . C1 C 0.0510(3) -0.01984(15) 0.11106(12) 0.0279(5) Uani 1 1 d . . . C2 C -0.2406(3) 0.02683(16) 0.17183(12) 0.0326(5) Uani 1 1 d . . . H2 H -0.3782 0.0078 0.1963 0.039 Uiso 1 1 calc R . . C3 C -0.1580(3) 0.12688(16) 0.16294(12) 0.0324(5) Uani 1 1 d . . . H3 H -0.2348 0.1748 0.1818 0.039 Uiso 1 1 calc R . . C4 C 0.0410(3) 0.15523(15) 0.12554(12) 0.0290(5) Uani 1 1 d . . . C5 C 0.1836(3) 0.24863(15) 0.10814(12) 0.0307(5) Uani 1 1 d . . . C6 C 0.1783(4) 0.34781(16) 0.12314(13) 0.0390(6) Uani 1 1 d . . . H6 H 0.0566 0.3649 0.1485 0.047 Uiso 1 1 calc R . . C7 C 0.3513(4) 0.42059(17) 0.10085(14) 0.0466(6) Uani 1 1 d . . . H7 H 0.3483 0.4885 0.1102 0.056 Uiso 1 1 calc R . . C8 C 0.5324(4) 0.39530(17) 0.06431(14) 0.0436(6) Uani 1 1 d . . . H8 H 0.6514 0.4469 0.0503 0.052 Uiso 1 1 calc R . . C9 C 0.5429(3) 0.29842(16) 0.04821(13) 0.0361(5) Uani 1 1 d . . . H9 H 0.6657 0.2821 0.0230 0.043 Uiso 1 1 calc R . . C10 C 0.3662(3) 0.22487(16) 0.07026(12) 0.0308(5) Uani 1 1 d . . . C11 C 0.1438(3) 0.07938(15) 0.09704(12) 0.0275(5) Uani 1 1 d . . . C12 C 0.1725(3) -0.09768(15) 0.09045(12) 0.0285(5) Uani 1 1 d . . . C13 C 0.1252(3) -0.19607(15) 0.12851(12) 0.0291(5) Uani 1 1 d . . . C14 C -0.0858(3) -0.25656(16) 0.12966(13) 0.0379(5) Uani 1 1 d . . . H14 H -0.2112 -0.2347 0.1071 0.046 Uiso 1 1 calc R . . C15 C -0.1117(4) -0.34858(18) 0.16384(16) 0.0506(7) Uani 1 1 d . . . H15 H -0.2549 -0.3912 0.1624 0.061 Uiso 1 1 calc R . . C16 C 0.0690(4) -0.37941(18) 0.20011(15) 0.0507(7) Uani 1 1 d . . . H16 H 0.0487 -0.4424 0.2244 0.061 Uiso 1 1 calc R . . C17 C 0.2771(4) -0.31947(17) 0.20113(14) 0.0441(6) Uani 1 1 d . . . H17 H 0.4005 -0.3400 0.2273 0.053 Uiso 1 1 calc R . . C18 C 0.3062(3) -0.22918(16) 0.16389(13) 0.0360(5) Uani 1 1 d . . . H18 H 0.4511 -0.1890 0.1623 0.043 Uiso 1 1 calc R . . O1' O 0.8181(2) 0.90517(10) 0.47296(9) 0.0366(4) Uani 1 1 d . . . N1' N 0.2863(3) 0.88082(13) 0.36847(10) 0.0329(4) Uani 1 1 d . . . N2' N 0.7845(2) 1.08642(12) 0.41134(10) 0.0301(4) Uani 1 1 d . . . H1' H 0.8865 1.0683 0.4451 0.053(7) Uiso 1 1 d R . . C1' C 0.4937(3) 0.92545(15) 0.39907(12) 0.0285(5) Uani 1 1 d . . . C2' C 0.1618(3) 0.93640(16) 0.32995(12) 0.0333(5) Uani 1 1 d . . . H2' H 0.0148 0.9045 0.3097 0.040 Uiso 1 1 calc R . . C3' C 0.2311(3) 1.03653(16) 0.31745(12) 0.0310(5) Uani 1 1 d . . . H3' H 0.1349 1.0722 0.2898 0.037 Uiso 1 1 calc R . . C4' C 0.4462(3) 1.08326(15) 0.34675(12) 0.0271(5) Uani 1 1 d . . . C5' C 0.5827(3) 1.18174(15) 0.34156(12) 0.0283(5) Uani 1 1 d . . . C6' C 0.5511(3) 1.26752(15) 0.30375(13) 0.0339(5) Uani 1 1 d . . . H6' H 0.4106 1.2704 0.2776 0.041 Uiso 1 1 calc R . . C7' C 0.7267(4) 1.34771(16) 0.30510(13) 0.0391(6) Uani 1 1 d . . . H7' H 0.7076 1.4065 0.2792 0.047 Uiso 1 1 calc R . . C8' C 0.9343(4) 1.34437(16) 0.34408(14) 0.0407(6) Uani 1 1 d . . . H8' H 1.0535 1.4009 0.3436 0.049 Uiso 1 1 calc R . . C9' C 0.9696(3) 1.26127(15) 0.38305(13) 0.0352(5) Uani 1 1 d . . . H9' H 1.1100 1.2597 0.4101 0.042 Uiso 1 1 calc R . . C10' C 0.7919(3) 1.17956(15) 0.38138(12) 0.0296(5) Uani 1 1 d . . . C11' C 0.5784(3) 1.02665(15) 0.39005(12) 0.0263(5) Uani 1 1 d . . . C12' C 0.6370(3) 0.86329(15) 0.43711(12) 0.0298(5) Uani 1 1 d . . . C13' C 0.5762(3) 0.75326(15) 0.42569(12) 0.0297(5) Uani 1 1 d . . . C14' C 0.3702(3) 0.69578(16) 0.44054(13) 0.0361(5) Uani 1 1 d . . . H14' H 0.2567 0.7268 0.4571 0.043 Uiso 1 1 calc R . . C15' C 0.3304(3) 0.59394(16) 0.43132(14) 0.0413(6) Uani 1 1 d . . . H15' H 0.1909 0.5550 0.4437 0.050 Uiso 1 1 calc R . . C16' C 0.4915(4) 0.54739(17) 0.40414(14) 0.0440(6) Uani 1 1 d . . . H16' H 0.4616 0.4771 0.3965 0.053 Uiso 1 1 calc R . . C17' C 0.6958(4) 0.60452(17) 0.38840(14) 0.0437(6) Uani 1 1 d . . . H17' H 0.8062 0.5733 0.3691 0.052 Uiso 1 1 calc R . . C18' C 0.7405(3) 0.70612(16) 0.40038(13) 0.0366(5) Uani 1 1 d . . . H18' H 0.8833 0.7445 0.3915 0.044 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 O1 0.0290(8) 0.0409(9) 0.0401(9) 0.0016(7) 0.0107(7) 0.0116(7) N1 0.0241(9) 0.0431(11) 0.0273(9) -0.0008(8) 0.0009(7) 0.0102(8) N2 0.0279(10) 0.0362(11) 0.0320(10) -0.0011(8) 0.0063(8) 0.0137(8) C1 0.0216(11) 0.0395(13) 0.0241(11) -0.0009(9) -0.0011(9) 0.0114(9) C2 0.0223(11) 0.0490(15) 0.0287(12) -0.0031(10) 0.0024(9) 0.0136(10) C3 0.0271(11) 0.0465(14) 0.0281(12) -0.0015(10) -0.0005(9) 0.0191(10) C4 0.0271(11) 0.0383(13) 0.0244(11) 0.0004(9) -0.0023(9) 0.0152(10) C5 0.0309(12) 0.0396(14) 0.0256(11) 0.0006(10) 0.0002(9) 0.0173(10) C6 0.0410(14) 0.0452(15) 0.0367(13) 0.0024(11) 0.0054(10) 0.0215(12) C7 0.0535(16) 0.0382(14) 0.0529(15) 0.0044(12) 0.0060(12) 0.0201(12) C8 0.0459(14) 0.0391(15) 0.0462(15) 0.0063(11) 0.0067(11) 0.0092(11) C9 0.0341(12) 0.0417(14) 0.0345(13) 0.0030(10) 0.0051(10) 0.0119(11) C10 0.0317(12) 0.0369(13) 0.0264(11) 0.0018(9) -0.0012(9) 0.0142(10) C11 0.0232(11) 0.0397(13) 0.0216(11) 0.0004(9) -0.0012(8) 0.0124(10) C12 0.0203(11) 0.0379(13) 0.0267(11) -0.0037(9) 0.0002(9) 0.0063(9) C13 0.0273(11) 0.0339(13) 0.0271(11) -0.0044(9) 0.0048(9) 0.0091(10) C14 0.0304(12) 0.0410(15) 0.0428(14) -0.0026(11) 0.0071(10) 0.0086(11) C15 0.0381(14) 0.0446(16) 0.0669(17) -0.0004(13) 0.0163(12) 0.0014(12) C16 0.0610(17) 0.0399(15) 0.0577(17) 0.0121(12) 0.0235(13) 0.0181(13) C17 0.0462(15) 0.0452(15) 0.0469(15) 0.0045(12) 0.0084(11) 0.0210(12) C18 0.0322(12) 0.0384(14) 0.0395(13) -0.0024(11) 0.0034(10) 0.0126(10) O1' 0.0274(8) 0.0423(9) 0.0395(9) 0.0001(7) -0.0062(7) 0.0096(7) N1' 0.0255(9) 0.0443(12) 0.0287(10) -0.0015(8) -0.0018(8) 0.0089(8) N2' 0.0224(9) 0.0387(11) 0.0296(10) 0.0019(8) -0.0015(8) 0.0087(8) C1' 0.0253(11) 0.0365(13) 0.0245(11) -0.0026(9) 0.0018(9) 0.0096(10) C2' 0.0199(11) 0.0471(15) 0.0321(12) -0.0003(10) -0.0030(9) 0.0080(10) C3' 0.0251(11) 0.0435(14) 0.0272(11) 0.0010(10) -0.0009(9) 0.0148(10) C4' 0.0249(11) 0.0365(13) 0.0221(11) -0.0029(9) 0.0037(8) 0.0116(9) C5' 0.0257(11) 0.0365(13) 0.0249(11) -0.0035(9) 0.0014(9) 0.0129(10) C6' 0.0324(12) 0.0379(14) 0.0348(12) -0.0028(10) 0.0014(10) 0.0159(10) C7' 0.0450(14) 0.0345(14) 0.0400(14) 0.0008(10) 0.0028(11) 0.0143(11) C8' 0.0386(13) 0.0370(14) 0.0440(14) -0.0015(11) 0.0032(11) 0.0041(11) C9' 0.0288(12) 0.0399(14) 0.0356(13) -0.0030(10) 0.0004(10) 0.0066(10) C10' 0.0278(11) 0.0360(13) 0.0266(11) -0.0025(9) 0.0016(9) 0.0112(10) C11' 0.0209(10) 0.0364(13) 0.0223(10) -0.0009(9) 0.0009(8) 0.0087(9) C12' 0.0227(11) 0.0424(14) 0.0244(11) 0.0000(10) 0.0025(9) 0.0080(10) C13' 0.0279(11) 0.0348(13) 0.0262(11) 0.0025(9) -0.0023(9) 0.0077(10) C14' 0.0308(12) 0.0426(15) 0.0360(13) 0.0015(10) 0.0023(10) 0.0108(11) C15' 0.0332(13) 0.0410(15) 0.0478(15) 0.0062(11) 0.0042(11) 0.0034(11) C16' 0.0438(14) 0.0360(14) 0.0525(15) 0.0037(11) 0.0011(12) 0.0107(11) C17' 0.0365(14) 0.0428(16) 0.0550(16) 0.0010(12) 0.0035(11) 0.0161(12) C18' 0.0283(12) 0.0395(14) 0.0431(14) 0.0036(11) 0.0003(10) 0.0106(10) _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 O1 C12 1.234(2) . ? N1 C2 1.346(2) . ? N1 C1 1.349(2) . ? N2 C11 1.370(2) . ? N2 C10 1.377(2) . ? N2 H1 0.8194 . ? C1 C11 1.397(3) . ? C1 C12 1.487(3) . ? C2 C3 1.381(3) . ? C2 H2 0.9500 . ? C3 C4 1.389(3) . ? C3 H3 0.9500 . ? C4 C11 1.420(3) . ? C4 C5 1.441(3) . ? C5 C6 1.392(3) . ? C5 C10 1.414(3) . ? C6 C7 1.374(3) . ? C6 H6 0.9500 . ? C7 C8 1.404(3) . ? C7 H7 0.9500 . ? C8 C9 1.372(3) . ? C8 H8 0.9500 . ? C9 C10 1.393(3) . ? C9 H9 0.9500 . ? C12 C13 1.484(3) . ? C13 C14 1.392(3) . ? C13 C18 1.397(3) . ? C14 C15 1.381(3) . ? C14 H14 0.9500 . ? C15 C16 1.384(3) . ? C15 H15 0.9500 . ? C16 C17 1.371(3) . ? C16 H16 0.9500 . ? C17 C18 1.379(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? O1' C12' 1.233(2) . ? N1' C2' 1.339(2) . ? N1' C1' 1.347(2) . ? N2' C11' 1.374(2) . ? N2' C10' 1.381(2) . ? N2' H1' 0.8842 . ? C1' C11' 1.398(3) . ? C1' C12' 1.484(3) . ? C2' C3' 1.382(3) . ? C2' H2' 0.9500 . ? C3' C4' 1.389(3) . ? C3' H3' 0.9500 . ? C4' C11' 1.416(2) . ? C4' C5' 1.444(3) . ? C5' C6' 1.393(3) . ? C5' C10' 1.412(3) . ? C6' C7' 1.371(3) . ? C6' H6' 0.9500 . ? C7' C8' 1.402(3) . ? C7' H7' 0.9500 . ? C8' C9' 1.375(3) . ? C8' H8' 0.9500 . ? C9' C10' 1.392(3) . ? C9' H9' 0.9500 . ? C12' C13' 1.486(3) . ? C13' C14' 1.389(3) . ? C13' C18' 1.402(3) . ? C14' C15' 1.376(3) . ? C14' H14' 0.9500 . ? C15' C16' 1.389(3) . ? C15' H15' 0.9500 . ? C16' C17' 1.382(3) . ? C16' H16' 0.9500 . ? C17' C18' 1.374(3) . ? C17' H17' 0.9500 . ? C18' H18' 0.9500 . ? 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 N1 C1 118.00(18) . . ? C11 N2 C10 109.62(17) . . ? C11 N2 H1 123.5 . . ? C10 N2 H1 126.4 . . ? N1 C1 C11 121.00(17) . . ? N1 C1 C12 119.00(18) . . ? C11 C1 C12 119.85(17) . . ? N1 C2 C3 125.01(19) . . ? N1 C2 H2 117.5 . . ? C3 C2 H2 117.5 . . ? C2 C3 C4 117.85(18) . . ? C2 C3 H3 121.1 . . ? C4 C3 H3 121.1 . . ? C3 C4 C11 117.95(19) . . ? C3 C4 C5 135.13(19) . . ? C11 C4 C5 106.90(17) . . ? C6 C5 C10 119.44(19) . . ? C6 C5 C4 134.47(19) . . ? C10 C5 C4 106.05(17) . . ? C7 C6 C5 119.2(2) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C6 C7 C8 120.4(2) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C9 C8 C7 122.0(2) . . ? C9 C8 H8 119.0 . . ? C7 C8 H8 119.0 . . ? C8 C9 C10 117.3(2) . . ? C8 C9 H9 121.3 . . ? C10 C9 H9 121.3 . . ? N2 C10 C9 129.35(18) . . ? N2 C10 C5 109.03(18) . . ? C9 C10 C5 121.6(2) . . ? N2 C11 C1 131.38(18) . . ? N2 C11 C4 108.39(18) . . ? C1 C11 C4 120.08(18) . . ? O1 C12 C13 119.38(17) . . ? O1 C12 C1 117.90(19) . . ? C13 C12 C1 122.37(17) . . ? C14 C13 C18 119.0(2) . . ? C14 C13 C12 124.00(18) . . ? C18 C13 C12 116.96(17) . . ? C15 C14 C13 119.6(2) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C16 120.6(2) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C17 C16 C15 120.3(2) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C18 119.6(2) . . ? C16 C17 H17 120.2 . . ? C18 C17 H17 120.2 . . ? C17 C18 C13 120.8(2) . . ? C17 C18 H18 119.6 . . ? C13 C18 H18 119.6 . . ? C2' N1' C1' 118.15(18) . . ? C11' N2' C10' 109.31(16) . . ? C11' N2' H1' 123.2 . . ? C10' N2' H1' 127.0 . . ? N1' C1' C11' 121.14(17) . . ? N1' C1' C12' 118.44(18) . . ? C11' C1' C12' 120.27(18) . . ? N1' C2' C3' 124.99(19) . . ? N1' C2' H2' 117.5 . . ? C3' C2' H2' 117.5 . . ? C2' C3' C4' 117.64(18) . . ? C2' C3' H3' 121.2 . . ? C4' C3' H3' 121.2 . . ? C3' C4' C11' 118.31(19) . . ? C3' C4' C5' 134.64(18) . . ? C11' C4' C5' 107.02(17) . . ? C6' C5' C10' 119.78(19) . . ? C6' C5' C4' 134.12(18) . . ? C10' C5' C4' 105.98(17) . . ? C7' C6' C5' 118.66(19) . . ? C7' C6' H6' 120.7 . . ? C5' C6' H6' 120.7 . . ? C6' C7' C8' 121.1(2) . . ? C6' C7' H7' 119.5 . . ? C8' C7' H7' 119.5 . . ? C9' C8' C7' 121.6(2) . . ? C9' C8' H8' 119.2 . . ? C7' C8' H8' 119.2 . . ? C8' C9' C10' 117.5(2) . . ? C8' C9' H9' 121.3 . . ? C10' C9' H9' 121.3 . . ? N2' C10' C9' 129.36(18) . . ? N2' C10' C5' 109.15(17) . . ? C9' C10' C5' 121.4(2) . . ? N2' C11' C1' 131.61(18) . . ? N2' C11' C4' 108.52(18) . . ? C1' C11' C4' 119.72(18) . . ? O1' C12' C1' 118.37(19) . . ? O1' C12' C13' 119.89(17) . . ? C1' C12' C13' 121.49(17) . . ? C14' C13' C18' 119.1(2) . . ? C14' C13' C12' 123.81(18) . . ? C18' C13' C12' 117.07(18) . . ? C15' C14' C13' 120.0(2) . . ? C15' C14' H14' 120.0 . . ? C13' C14' H14' 120.0 . . ? C14' C15' C16' 120.8(2) . . ? C14' C15' H15' 119.6 . . ? C16' C15' H15' 119.6 . . ? C17' C16' C15' 119.2(2) . . ? C17' C16' H16' 120.4 . . ? C15' C16' H16' 120.4 . . ? C18' C17' C16' 120.6(2) . . ? C18' C17' H17' 119.7 . . ? C16' C17' H17' 119.7 . . ? C17' C18' C13' 120.2(2) . . ? C17' C18' H18' 119.9 . . ? C13' C18' H18' 119.9 . . ? 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 C2 N1 C1 C11 0.0(3) . . . . ? C2 N1 C1 C12 175.56(16) . . . . ? C1 N1 C2 C3 -2.1(3) . . . . ? N1 C2 C3 C4 1.3(3) . . . . ? C2 C3 C4 C11 1.5(3) . . . . ? C2 C3 C4 C5 -177.0(2) . . . . ? C3 C4 C5 C6 0.9(4) . . . . ? C11 C4 C5 C6 -177.7(2) . . . . ? C3 C4 C5 C10 178.4(2) . . . . ? C11 C4 C5 C10 -0.2(2) . . . . ? C10 C5 C6 C7 -0.1(3) . . . . ? C4 C5 C6 C7 177.1(2) . . . . ? C5 C6 C7 C8 -0.8(3) . . . . ? C6 C7 C8 C9 1.1(3) . . . . ? C7 C8 C9 C10 -0.5(3) . . . . ? C11 N2 C10 C9 176.7(2) . . . . ? C11 N2 C10 C5 -1.2(2) . . . . ? C8 C9 C10 N2 -178.10(19) . . . . ? C8 C9 C10 C5 -0.3(3) . . . . ? C6 C5 C10 N2 178.81(17) . . . . ? C4 C5 C10 N2 0.9(2) . . . . ? C6 C5 C10 C9 0.6(3) . . . . ? C4 C5 C10 C9 -177.28(18) . . . . ? C10 N2 C11 C1 -174.27(19) . . . . ? C10 N2 C11 C4 1.1(2) . . . . ? N1 C1 C11 N2 177.63(18) . . . . ? C12 C1 C11 N2 2.1(3) . . . . ? N1 C1 C11 C4 2.7(3) . . . . ? C12 C1 C11 C4 -172.80(17) . . . . ? C3 C4 C11 N2 -179.40(16) . . . . ? C5 C4 C11 N2 -0.5(2) . . . . ? C3 C4 C11 C1 -3.4(3) . . . . ? C5 C4 C11 C1 175.47(16) . . . . ? N1 C1 C12 O1 170.67(17) . . . . ? C11 C1 C12 O1 -13.7(3) . . . . ? N1 C1 C12 C13 -16.2(3) . . . . ? C11 C1 C12 C13 159.39(17) . . . . ? O1 C12 C13 C14 -136.9(2) . . . . ? C1 C12 C13 C14 50.0(3) . . . . ? O1 C12 C13 C18 42.1(3) . . . . ? C1 C12 C13 C18 -130.92(19) . . . . ? C18 C13 C14 C15 -1.4(3) . . . . ? C12 C13 C14 C15 177.60(19) . . . . ? C13 C14 C15 C16 2.7(3) . . . . ? C14 C15 C16 C17 -1.2(4) . . . . ? C15 C16 C17 C18 -1.6(3) . . . . ? C16 C17 C18 C13 2.9(3) . . . . ? C14 C13 C18 C17 -1.4(3) . . . . ? C12 C13 C18 C17 179.56(18) . . . . ? C2' N1' C1' C11' -0.8(3) . . . . ? C2' N1' C1' C12' -176.36(17) . . . . ? C1' N1' C2' C3' 1.3(3) . . . . ? N1' C2' C3' C4' 0.2(3) . . . . ? C2' C3' C4' C11' -2.2(3) . . . . ? C2' C3' C4' C5' 175.2(2) . . . . ? C3' C4' C5' C6' -1.2(4) . . . . ? C11' C4' C5' C6' 176.4(2) . . . . ? C3' C4' C5' C10' -177.1(2) . . . . ? C11' C4' C5' C10' 0.5(2) . . . . ? C10' C5' C6' C7' 1.0(3) . . . . ? C4' C5' C6' C7' -174.4(2) . . . . ? C5' C6' C7' C8' -0.4(3) . . . . ? C6' C7' C8' C9' -0.6(3) . . . . ? C7' C8' C9' C10' 0.9(3) . . . . ? C11' N2' C10' C9' -175.22(19) . . . . ? C11' N2' C10' C5' 1.8(2) . . . . ? C8' C9' C10' N2' 176.42(19) . . . . ? C8' C9' C10' C5' -0.3(3) . . . . ? C6' C5' C10' N2' -178.00(16) . . . . ? C4' C5' C10' N2' -1.4(2) . . . . ? C6' C5' C10' C9' -0.7(3) . . . . ? C4' C5' C10' C9' 175.88(18) . . . . ? C10' N2' C11' C1' 173.89(19) . . . . ? C10' N2' C11' C4' -1.4(2) . . . . ? N1' C1' C11' N2' -176.00(18) . . . . ? C12' C1' C11' N2' -0.5(3) . . . . ? N1' C1' C11' C4' -1.1(3) . . . . ? C12' C1' C11' C4' 174.33(17) . . . . ? C3' C4' C11' N2' 178.58(16) . . . . ? C5' C4' C11' N2' 0.5(2) . . . . ? C3' C4' C11' C1' 2.6(3) . . . . ? C5' C4' C11' C1' -175.44(16) . . . . ? N1' C1' C12' O1' -172.63(17) . . . . ? C11' C1' C12' O1' 11.8(3) . . . . ? N1' C1' C12' C13' 13.2(3) . . . . ? C11' C1' C12' C13' -162.40(18) . . . . ? O1' C12' C13' C14' 136.2(2) . . . . ? C1' C12' C13' C14' -49.7(3) . . . . ? O1' C12' C13' C18' -42.2(3) . . . . ? C1' C12' C13' C18' 131.88(19) . . . . ? C18' C13' C14' C15' 0.8(3) . . . . ? C12' C13' C14' C15' -177.66(18) . . . . ? C13' C14' C15' C16' -2.4(3) . . . . ? C14' C15' C16' C17' 1.7(3) . . . . ? C15' C16' C17' C18' 0.8(3) . . . . ? C16' C17' C18' C13' -2.4(3) . . . . ? C14' C13' C18' C17' 1.6(3) . . . . ? C12' C13' C18' C17' -179.84(18) . . . . ? 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 N2' H1' O1' 0.88 2.27 2.767(2) 115.7 . N2' H1' O1' 0.88 2.12 2.944(2) 154.2 2_776 N2 H1 O1 0.82 2.27 2.744(2) 117.2 . N2 H1 O1 0.82 2.18 2.945(2) 154.9 2_655 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.210 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.037