# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_a12609 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H14 Br N O' _chemical_formula_sum 'C21 H14 Br N O' _chemical_formula_weight 376.24 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 'P n a 21' 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' _cell_length_a 20.1931(14) _cell_length_b 20.0328(12) _cell_length_c 3.9753(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1608.11(19) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 2.563 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3852 _exptl_absorpt_correction_T_max 0.9505 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10631 _diffrn_reflns_av_R_equivalents 0.0512 _diffrn_reflns_av_sigmaI/netI 0.0487 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 2 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2301 _reflns_number_gt 1943 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0416P)^2^+2.2617P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.21(2) _refine_ls_number_reflns 2301 _refine_ls_number_parameters 217 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0554 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1002 _refine_ls_wR_factor_gt 0.0959 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 C1 C 0.4017(3) 0.5576(2) 0.4365(16) 0.0285(15) Uani 1 1 d . . . C2 C 0.3579(3) 0.5968(3) 0.6130(19) 0.0343(16) Uani 1 1 d . . . H2 H 0.3147 0.5809 0.6625 0.041 Uiso 1 1 calc R . . C3 C 0.3777(3) 0.6603(2) 0.7188(16) 0.0287(19) Uani 1 1 d . . . H3 H 0.3480 0.6874 0.8438 0.034 Uiso 1 1 calc R . . C4 C 0.4405(3) 0.6840(2) 0.6421(16) 0.0257(14) Uani 1 1 d . . . C5 C 0.4824(3) 0.6439(3) 0.4564(17) 0.0281(14) Uani 1 1 d . . . H5 H 0.5251 0.6599 0.3977 0.034 Uiso 1 1 calc R . . C6 C 0.4631(3) 0.5806(2) 0.3540(19) 0.0295(16) Uani 1 1 d . . . H6 H 0.4925 0.5534 0.2272 0.035 Uiso 1 1 calc R . . C7 C 0.4605(3) 0.7507(2) 0.7629(19) 0.0258(13) Uani 1 1 d . . . C8 C 0.5175(2) 0.7877(2) 0.778(2) 0.0302(13) Uani 1 1 d . . . C9 C 0.5874(3) 0.7734(2) 0.6844(16) 0.0303(17) Uani 1 1 d . . . C10 C 0.6170(3) 0.7137(2) 0.771(3) 0.0350(14) Uani 1 1 d . . . H10 H 0.5921 0.6802 0.8834 0.042 Uiso 1 1 calc R . . C11 C 0.6836(3) 0.7025(3) 0.6943(19) 0.044(2) Uani 1 1 d . . . H11 H 0.7038 0.6614 0.7546 0.053 Uiso 1 1 calc R . . C12 C 0.7204(3) 0.7512(3) 0.5300(19) 0.042(2) Uani 1 1 d . . . H12 H 0.7656 0.7437 0.4761 0.050 Uiso 1 1 calc R . . C13 C 0.6897(3) 0.8112(3) 0.4459(19) 0.0438(19) Uani 1 1 d . . . H13 H 0.7144 0.8451 0.3361 0.053 Uiso 1 1 calc R . . C14 C 0.6241(3) 0.8220(3) 0.5190(17) 0.0360(16) Uani 1 1 d . . . H14 H 0.6038 0.8629 0.4563 0.043 Uiso 1 1 calc R . . C15 C 0.4397(3) 0.8482(2) 0.9752(17) 0.0277(15) Uani 1 1 d . . . C16 C 0.3974(3) 0.9001(2) 1.1293(18) 0.0279(14) Uani 1 1 d . . . C17 C 0.3300(3) 0.8915(3) 1.1635(18) 0.0346(17) Uani 1 1 d . . . H17 H 0.3101 0.8513 1.0873 0.041 Uiso 1 1 calc R . . C18 C 0.2905(3) 0.9410(3) 1.308(3) 0.0440(16) Uani 1 1 d . . . H18 H 0.2442 0.9348 1.3334 0.053 Uiso 1 1 calc R . . C19 C 0.3208(3) 0.9993(3) 1.4141(17) 0.0378(17) Uani 1 1 d . . . H19 H 0.2944 1.0341 1.5066 0.045 Uiso 1 1 calc R . . C20 C 0.3873(3) 1.0080(3) 1.3887(17) 0.0348(18) Uani 1 1 d . . . H20 H 0.4072 1.0477 1.4717 0.042 Uiso 1 1 calc R . . C21 C 0.4264(3) 0.9588(2) 1.2411(19) 0.0268(16) Uani 1 1 d . . . H21 H 0.4727 0.9654 1.2171 0.032 Uiso 1 1 calc R . . N1 N 0.5021(2) 0.85051(19) 0.9108(13) 0.0283(13) Uani 1 1 d . . . O1 O 0.40998(18) 0.78951(16) 0.8927(11) 0.0288(11) Uani 1 1 d . . . Br1 Br 0.37492(3) 0.47146(2) 0.2987(3) 0.0416(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.036(3) 0.017(2) 0.032(4) 0.000(3) -0.017(3) 0.000(2) C2 0.024(3) 0.034(3) 0.045(5) 0.006(3) -0.006(3) -0.003(2) C3 0.031(3) 0.027(2) 0.028(6) -0.001(3) -0.001(3) 0.006(2) C4 0.032(3) 0.022(2) 0.023(3) 0.006(2) -0.009(3) 0.002(2) C5 0.027(3) 0.028(3) 0.030(4) -0.001(3) 0.000(3) -0.001(2) C6 0.032(3) 0.028(2) 0.030(5) 0.004(3) -0.001(3) 0.004(2) C7 0.036(3) 0.026(2) 0.016(4) -0.005(3) 0.003(4) 0.0061(19) C8 0.033(3) 0.021(2) 0.037(4) -0.008(4) -0.012(4) 0.0007(19) C9 0.032(3) 0.027(3) 0.032(5) -0.006(3) 0.003(3) -0.003(2) C10 0.035(3) 0.028(2) 0.041(4) -0.009(4) 0.004(4) -0.005(2) C11 0.033(4) 0.037(3) 0.062(7) -0.006(3) -0.010(3) 0.005(3) C12 0.034(4) 0.039(3) 0.052(6) -0.013(3) 0.000(4) -0.006(3) C13 0.033(4) 0.041(3) 0.057(5) -0.005(4) 0.010(4) -0.014(3) C14 0.040(4) 0.028(3) 0.040(4) -0.003(3) -0.003(3) -0.006(3) C15 0.032(4) 0.019(3) 0.032(4) 0.000(3) -0.007(3) -0.002(2) C16 0.030(3) 0.019(2) 0.035(4) 0.005(3) -0.008(3) 0.000(2) C17 0.029(3) 0.030(3) 0.044(5) -0.004(3) -0.005(3) 0.000(2) C18 0.024(3) 0.053(3) 0.055(5) 0.017(5) -0.004(5) 0.001(2) C19 0.046(4) 0.031(3) 0.036(5) -0.005(3) 0.006(3) 0.016(3) C20 0.048(4) 0.021(2) 0.036(5) 0.002(3) -0.002(3) 0.000(2) C21 0.026(3) 0.026(2) 0.028(5) -0.001(3) -0.004(3) -0.0011(19) N1 0.031(3) 0.0191(19) 0.034(4) -0.004(2) -0.003(2) 0.0020(18) O1 0.028(2) 0.0231(16) 0.035(3) -0.0007(18) -0.0023(19) -0.0003(15) Br1 0.0460(3) 0.0287(2) 0.0502(4) -0.0097(4) -0.0039(5) -0.0079(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 C1 C6 1.362(8) . ? C1 C2 1.374(9) . ? C1 Br1 1.890(5) . ? C2 C3 1.398(8) . ? C3 C4 1.389(7) . ? C4 C5 1.380(8) . ? C4 C7 1.476(7) . ? C5 C6 1.388(7) . ? C7 C8 1.372(7) . ? C7 O1 1.382(6) . ? C8 N1 1.399(6) . ? C8 C9 1.487(8) . ? C9 C10 1.381(8) . ? C9 C14 1.390(8) . ? C10 C11 1.397(8) . ? C11 C12 1.389(9) . ? C12 C13 1.393(9) . ? C13 C14 1.372(8) . ? C15 N1 1.288(7) . ? C15 O1 1.360(6) . ? C15 C16 1.478(8) . ? C16 C17 1.378(8) . ? C16 C21 1.386(7) . ? C17 C18 1.395(9) . ? C18 C19 1.385(9) . ? C19 C20 1.359(8) . ? C20 C21 1.393(8) . ? 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 C6 C1 C2 121.0(5) . . ? C6 C1 Br1 119.9(5) . . ? C2 C1 Br1 119.0(4) . . ? C1 C2 C3 119.3(5) . . ? C4 C3 C2 120.4(5) . . ? C5 C4 C3 118.6(5) . . ? C5 C4 C7 122.3(5) . . ? C3 C4 C7 119.2(5) . . ? C4 C5 C6 121.1(5) . . ? C1 C6 C5 119.5(6) . . ? C8 C7 O1 107.4(4) . . ? C8 C7 C4 137.2(5) . . ? O1 C7 C4 115.4(4) . . ? C7 C8 N1 108.4(5) . . ? C7 C8 C9 132.9(5) . . ? N1 C8 C9 118.6(4) . . ? C10 C9 C14 119.6(6) . . ? C10 C9 C8 121.1(5) . . ? C14 C9 C8 119.3(5) . . ? C9 C10 C11 120.1(6) . . ? C12 C11 C10 120.3(6) . . ? C11 C12 C13 118.7(6) . . ? C14 C13 C12 121.0(6) . . ? C13 C14 C9 120.2(6) . . ? N1 C15 O1 114.5(5) . . ? N1 C15 C16 128.5(5) . . ? O1 C15 C16 117.0(5) . . ? C17 C16 C21 119.4(5) . . ? C17 C16 C15 121.6(5) . . ? C21 C16 C15 119.0(5) . . ? C16 C17 C18 121.0(5) . . ? C19 C18 C17 118.2(5) . . ? C20 C19 C18 121.5(6) . . ? C19 C20 C21 120.0(5) . . ? C16 C21 C20 119.8(5) . . ? C15 N1 C8 105.1(4) . . ? C15 O1 C7 104.6(4) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.803 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.070 _database_code_depnum_ccdc_archive 'CCDC 940035' ####################################################################### # # 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_ch15078 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H14 Br N O' _chemical_formula_sum 'C21 H14 Br N O' _chemical_formula_weight 376.24 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 'P 21/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 4.9890(12) _cell_length_b 19.768(6) _cell_length_c 16.305(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.553(7) _cell_angle_gamma 90.00 _cell_volume 1606.5(8) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.556 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 2.565 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4194 _exptl_absorpt_correction_T_max 0.9505 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11035 _diffrn_reflns_av_R_equivalents 0.0945 _diffrn_reflns_av_sigmaI/netI 0.1178 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2801 _reflns_number_gt 1579 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0772P)^2^+0.4221P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2801 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1269 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1664 _refine_ls_wR_factor_gt 0.1126 _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 C1 C -0.6196(12) 0.0593(3) 0.3781(4) 0.0303(18) Uani 1 1 d . . . C2 C -0.5707(13) 0.0882(3) 0.4548(4) 0.0364(18) Uani 1 1 d . . . H2 H -0.6629 0.0730 0.5011 0.044 Uiso 1 1 calc R . . C3 C -0.3825(13) 0.1401(3) 0.4621(5) 0.0369(19) Uani 1 1 d . . . H3 H -0.3461 0.1602 0.5144 0.044 Uiso 1 1 calc R . . C4 C -0.2474(12) 0.1632(3) 0.3957(4) 0.0264(16) Uani 1 1 d . . . C5 C -0.3051(13) 0.1340(4) 0.3199(5) 0.040(2) Uani 1 1 d . . . H5 H -0.2164 0.1498 0.2733 0.047 Uiso 1 1 calc R . . C6 C -0.4880(13) 0.0825(3) 0.3111(4) 0.0356(18) Uani 1 1 d . . . H6 H -0.5243 0.0628 0.2587 0.043 Uiso 1 1 calc R . . C7 C -0.0506(12) 0.2166(3) 0.4060(4) 0.0296(17) Uani 1 1 d . A . C8 C 0.2611(12) 0.2846(3) 0.3691(4) 0.0252(16) Uani 1 1 d . A . C9 C 0.4459(12) 0.3113(3) 0.3102(4) 0.0259(16) Uani 1 1 d . . . C10 C 0.4364(13) 0.2873(4) 0.2303(4) 0.0351(18) Uani 1 1 d . . . H10 H 0.3082 0.2537 0.2144 0.042 Uiso 1 1 calc R . . C11 C 0.6075(14) 0.3109(4) 0.1742(4) 0.041(2) Uani 1 1 d . . . H11 H 0.5986 0.2937 0.1198 0.050 Uiso 1 1 calc R . . C12 C 0.7960(13) 0.3604(4) 0.1968(5) 0.0372(19) Uani 1 1 d . . . H12 H 0.9163 0.3767 0.1578 0.045 Uiso 1 1 calc R . . C13 C 0.8075(13) 0.3854(4) 0.2753(5) 0.0353(18) Uani 1 1 d . . . H13 H 0.9340 0.4195 0.2907 0.042 Uiso 1 1 calc R . . C14 C 0.6328(12) 0.3605(3) 0.3325(4) 0.0291(17) Uani 1 1 d . . . H14 H 0.6420 0.3774 0.3871 0.035 Uiso 1 1 calc R . . C15 C 0.2040(12) 0.2965(3) 0.4482(4) 0.0257(16) Uani 1 1 d . A . C16 C 0.3034(12) 0.3478(3) 0.5087(4) 0.0263(16) Uani 1 1 d . . . C17 C 0.438(3) 0.3285(10) 0.5790(12) 0.031(5) Uani 0.50 1 d P A 1 H17 H 0.4777 0.2821 0.5885 0.038 Uiso 0.50 1 calc PR A 1 C18 C 0.518(3) 0.3762(10) 0.6364(11) 0.034(5) Uani 0.50 1 d P A 1 H18 H 0.6036 0.3623 0.6869 0.041 Uiso 0.50 1 calc PR A 1 C19 C 0.4750 0.4442 0.621(2) 0.039 Uiso 0.50 1 d P A 1 H19 H 0.5332 0.4772 0.6601 0.047 Uiso 0.50 1 calc PR A 1 C20 C 0.347(3) 0.4635(7) 0.5484(10) 0.036(4) Uani 0.50 1 d P A 1 H20 H 0.3103 0.5100 0.5382 0.043 Uiso 0.50 1 calc PR A 1 C21 C 0.270(3) 0.4151(7) 0.4894(9) 0.030(3) Uani 0.50 1 d P A 1 H21 H 0.1957 0.4284 0.4372 0.036 Uiso 0.50 1 calc PR A 1 C17' C 0.549(4) 0.3432(10) 0.5503(11) 0.031(5) Uani 0.50 1 d P A 2 H17' H 0.6644 0.3066 0.5384 0.038 Uiso 0.50 1 calc PR A 2 C18' C 0.631(4) 0.3890(9) 0.6074(10) 0.033(4) Uani 0.50 1 d P A 2 H18' H 0.8024 0.3833 0.6342 0.040 Uiso 0.50 1 calc PR A 2 C19' C 0.4750 0.4442 0.629(2) 0.030 Uiso 0.50 1 d P A 2 H19' H 0.5425 0.4783 0.6650 0.036 Uiso 0.50 1 calc PR A 2 C20' C 0.221(3) 0.4467(8) 0.5948(10) 0.042(4) Uani 0.50 1 d P A 2 H20' H 0.1049 0.4817 0.6114 0.051 Uiso 0.50 1 calc PR A 2 C21' C 0.126(3) 0.4001(7) 0.5369(9) 0.034(4) Uani 0.50 1 d P A 2 H21' H -0.0543 0.4025 0.5159 0.041 Uiso 0.50 1 calc PR A 2 N1 N 0.0046(10) 0.2524(3) 0.4711(3) 0.0289(14) Uani 1 1 d . . . O1 O 0.0975(8) 0.2324(2) 0.3418(3) 0.0291(11) Uani 1 1 d . . . Br1 Br -0.86676(14) -0.01389(4) 0.36577(5) 0.0457(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.023(4) 0.025(4) 0.042(5) -0.003(4) -0.012(3) 0.007(3) C2 0.037(4) 0.036(5) 0.036(5) 0.001(4) 0.005(3) -0.011(3) C3 0.037(4) 0.033(5) 0.040(5) -0.009(4) -0.005(4) -0.006(3) C4 0.025(4) 0.022(4) 0.032(4) 0.001(3) -0.004(3) 0.000(3) C5 0.040(4) 0.036(5) 0.042(5) 0.007(4) -0.005(4) -0.013(4) C6 0.041(4) 0.036(5) 0.029(4) -0.002(4) -0.009(3) 0.000(4) C7 0.027(4) 0.026(4) 0.035(5) 0.006(4) -0.005(3) 0.004(3) C8 0.021(3) 0.017(4) 0.036(5) -0.009(3) -0.006(3) -0.001(3) C9 0.020(3) 0.024(4) 0.034(4) -0.004(3) -0.001(3) 0.003(3) C10 0.028(4) 0.042(5) 0.036(5) -0.014(4) -0.001(3) -0.002(3) C11 0.041(5) 0.048(5) 0.035(5) -0.017(4) 0.001(4) 0.003(4) C12 0.030(4) 0.047(5) 0.035(5) 0.007(4) 0.013(3) 0.011(4) C13 0.031(4) 0.031(4) 0.044(5) 0.005(4) -0.001(4) 0.000(3) C14 0.030(4) 0.032(4) 0.026(4) -0.001(3) -0.002(3) 0.002(3) C15 0.026(4) 0.016(4) 0.034(4) 0.003(3) -0.012(3) -0.004(3) C16 0.029(4) 0.023(4) 0.027(4) 0.003(3) -0.001(3) -0.005(3) C17 0.026(11) 0.029(10) 0.039(13) 0.004(9) -0.005(8) -0.002(8) C18 0.036(11) 0.048(12) 0.019(11) 0.007(9) 0.001(8) -0.018(9) C20 0.053(11) 0.013(8) 0.040(10) -0.008(7) -0.009(8) 0.014(7) C21 0.040(9) 0.030(9) 0.020(9) -0.006(7) -0.010(7) 0.012(7) C17' 0.033(12) 0.033(12) 0.028(12) -0.010(9) -0.003(8) 0.013(8) C18' 0.038(11) 0.036(11) 0.023(11) 0.004(9) -0.013(8) 0.005(9) C20' 0.053(11) 0.041(11) 0.035(11) -0.005(9) 0.027(9) 0.012(8) C21' 0.043(9) 0.035(10) 0.023(9) 0.002(7) -0.003(7) -0.005(7) N1 0.039(3) 0.018(3) 0.029(3) 0.004(3) -0.009(3) -0.008(2) O1 0.026(3) 0.020(3) 0.041(3) -0.007(2) -0.002(2) -0.003(2) Br1 0.0347(4) 0.0347(5) 0.0668(6) -0.0037(4) -0.0082(4) -0.0091(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.378(9) . ? C1 C2 1.387(9) . ? C1 Br1 1.906(6) . ? C2 C3 1.392(9) . ? C2 H2 0.9500 . ? C3 C4 1.379(9) . ? C3 H3 0.9500 . ? C4 C5 1.382(9) . ? C4 C7 1.446(9) . ? C5 C6 1.370(9) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 N1 1.295(8) . ? C7 O1 1.345(8) . ? C8 C15 1.354(9) . ? C8 O1 1.378(7) . ? C8 C9 1.460(9) . ? C9 C14 1.385(8) . ? C9 C10 1.386(9) . ? C10 C11 1.361(9) . ? C10 H10 0.9500 . ? C11 C12 1.394(9) . ? C11 H11 0.9500 . ? C12 C13 1.371(9) . ? C12 H12 0.9500 . ? C13 C14 1.394(9) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 N1 1.387(8) . ? C15 C16 1.484(8) . ? C16 C17 1.36(2) . ? C16 C21 1.376(15) . ? C16 C17' 1.377(19) . ? C16 C21' 1.450(16) . ? C17 C18 1.37(3) . ? C17 H17 0.9500 . ? C18 C19 1.38(2) . ? C18 H18 0.9500 . ? C19 C20 1.37(3) . ? C19 H19 0.9500 . ? C20 C21 1.397(18) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C17' C18' 1.35(2) . ? C17' H17' 0.9500 . ? C18' C19' 1.39(2) . ? C18' H18' 0.9500 . ? C19' C20' 1.36(2) . ? C19' H19' 0.9500 . ? C20' C21' 1.387(19) . ? C20' H20' 0.9500 . ? C21' H21' 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 C6 C1 C2 120.5(6) . . ? C6 C1 Br1 119.9(5) . . ? C2 C1 Br1 119.7(6) . . ? C1 C2 C3 118.1(7) . . ? C1 C2 H2 120.9 . . ? C3 C2 H2 120.9 . . ? C4 C3 C2 121.9(6) . . ? C4 C3 H3 119.1 . . ? C2 C3 H3 119.1 . . ? C3 C4 C5 118.3(6) . . ? C3 C4 C7 120.2(6) . . ? C5 C4 C7 121.5(7) . . ? C6 C5 C4 121.0(7) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C1 120.2(7) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? N1 C7 O1 114.0(6) . . ? N1 C7 C4 127.8(7) . . ? O1 C7 C4 118.2(6) . . ? C15 C8 O1 107.0(6) . . ? C15 C8 C9 136.8(6) . . ? O1 C8 C9 116.2(6) . . ? C14 C9 C10 118.8(6) . . ? C14 C9 C8 121.3(6) . . ? C10 C9 C8 119.9(6) . . ? C11 C10 C9 121.1(7) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C11 C12 120.0(7) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C13 C12 C11 119.9(7) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 119.8(7) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C9 C14 C13 120.4(6) . . ? C9 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C8 C15 N1 109.3(5) . . ? C8 C15 C16 132.4(6) . . ? N1 C15 C16 118.2(6) . . ? C17 C16 C21 121.0(11) . . ? C17 C16 C17' 33.8(7) . . ? C21 C16 C17' 105.9(11) . . ? C17 C16 C21' 102.7(11) . . ? C21 C16 C21' 46.5(7) . . ? C17' C16 C21' 115.7(11) . . ? C17 C16 C15 120.6(10) . . ? C21 C16 C15 118.3(7) . . ? C17' C16 C15 123.1(10) . . ? C21' C16 C15 120.5(7) . . ? C16 C17 C18 120.0(17) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C17 C18 C19 120(2) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C20 C19 C18 119.3(19) . . ? C20 C19 H19 120.3 . . ? C18 C19 H19 120.3 . . ? C19 C20 C21 120.4(12) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C16 C21 C20 118.5(12) . . ? C16 C21 H21 120.7 . . ? C20 C21 H21 120.7 . . ? C18' C17' C16 122.1(17) . . ? C18' C17' H17' 119.0 . . ? C16 C17' H17' 119.0 . . ? C17' C18' C19' 122.8(17) . . ? C17' C18' H18' 118.6 . . ? C19' C18' H18' 118.6 . . ? C20' C19' C18' 116.6(17) . . ? C20' C19' H19' 121.7 . . ? C18' C19' H19' 121.7 . . ? C19' C20' C21' 122.5(15) . . ? C19' C20' H20' 118.8 . . ? C21' C20' H20' 118.8 . . ? C20' C21' C16 119.6(12) . . ? C20' C21' H21' 120.2 . . ? C16 C21' H21' 120.2 . . ? C7 N1 C15 104.6(6) . . ? C7 O1 C8 105.1(5) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.429 _refine_diff_density_min -0.629 _refine_diff_density_rms 0.116 _database_code_depnum_ccdc_archive 'CCDC 940036' ####################################################################### # # 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_ch15011 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H16 Cl N O2' _chemical_formula_sum 'C22 H16 Cl N O2' _chemical_formula_weight 361.81 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9367(17) _cell_length_b 10.1803(18) _cell_length_c 18.333(3) _cell_angle_alpha 77.518(9) _cell_angle_beta 87.401(7) _cell_angle_gamma 73.963(8) _cell_volume 1740.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.79 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.236 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8356 _exptl_absorpt_correction_T_max 0.9906 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14610 _diffrn_reflns_av_R_equivalents 0.0512 _diffrn_reflns_av_sigmaI/netI 0.0795 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.14 _diffrn_reflns_theta_max 25.19 _reflns_number_total 6162 _reflns_number_gt 3883 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1748P)^2^+1.4992P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6162 _refine_ls_number_parameters 469 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0966 _refine_ls_R_factor_gt 0.0550 _refine_ls_wR_factor_ref 0.2182 _refine_ls_wR_factor_gt 0.1565 _refine_ls_goodness_of_fit_ref 0.754 _refine_ls_restrained_S_all 0.754 _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 C1 C 0.5424(3) 0.8105(4) 0.94777(19) 0.0306(8) Uani 1 1 d . . . C2 C 0.5218(4) 0.9000(4) 0.8795(2) 0.0370(9) Uani 1 1 d . . . H2 H 0.4428 0.9797 0.8708 0.044 Uiso 1 1 calc R . . C3 C 0.6155(3) 0.8745(4) 0.8237(2) 0.0350(8) Uani 1 1 d . . . H3 H 0.6003 0.9366 0.7761 0.042 Uiso 1 1 calc R . . C4 C 0.7318(3) 0.7598(3) 0.83535(19) 0.0274(8) Uani 1 1 d . . . C5 C 0.7483(4) 0.6700(4) 0.9048(2) 0.0356(8) Uani 1 1 d . . . H5 H 0.8263 0.5894 0.9138 0.043 Uiso 1 1 calc R . . C6 C 0.6548(4) 0.6948(4) 0.9609(2) 0.0401(9) Uani 1 1 d . . . H6 H 0.6680 0.6323 1.0083 0.048 Uiso 1 1 calc R . . C7 C 0.8369(3) 0.7345(3) 0.77821(19) 0.0267(7) Uani 1 1 d . . . C8 C 1.0359(3) 0.6212(3) 0.74175(19) 0.0286(8) Uani 1 1 d . . . C9 C 1.1644(3) 0.5097(3) 0.7478(2) 0.0309(8) Uani 1 1 d . . . C10 C 1.1956(4) 0.4035(4) 0.8107(2) 0.0379(9) Uani 1 1 d . . . H10 H 1.1315 0.4026 0.8507 0.045 Uiso 1 1 calc R . . C11 C 1.3187(4) 0.2994(4) 0.8160(2) 0.0459(10) Uani 1 1 d . . . H11 H 1.3395 0.2269 0.8596 0.055 Uiso 1 1 calc R . . C12 C 1.4120(4) 0.2997(4) 0.7582(3) 0.0485(11) Uani 1 1 d . . . H12 H 1.4973 0.2274 0.7619 0.058 Uiso 1 1 calc R . . C13 C 1.3819(4) 0.4049(4) 0.6950(2) 0.0428(10) Uani 1 1 d . . . H13 H 1.4464 0.4051 0.6552 0.051 Uiso 1 1 calc R . . C14 C 1.2588(3) 0.5094(4) 0.6894(2) 0.0348(9) Uani 1 1 d . . . H14 H 1.2381 0.5815 0.6457 0.042 Uiso 1 1 calc R . . C15 C 0.8656(3) 0.8028(3) 0.71014(18) 0.0258(7) Uani 1 1 d . . . C16 C 0.7871(3) 0.9344(3) 0.66152(18) 0.0265(7) Uani 1 1 d . . . C17 C 0.8501(3) 1.0419(3) 0.63685(19) 0.0324(8) Uani 1 1 d . . . H17 H 0.9440 1.0294 0.6515 0.039 Uiso 1 1 calc R . . C18 C 0.7791(3) 1.1652(4) 0.5919(2) 0.0346(9) Uani 1 1 d . . . H18 H 0.8232 1.2382 0.5765 0.042 Uiso 1 1 calc R . . C19 C 0.6440(3) 1.1839(3) 0.56883(18) 0.0289(8) Uani 1 1 d . . . C20 C 0.4456(4) 1.3324(4) 0.4953(2) 0.0449(10) Uani 1 1 d . . . H20A H 0.4149 1.4266 0.4639 0.067 Uiso 1 1 calc R . . H20B H 0.3812 1.3232 0.5370 0.067 Uiso 1 1 calc R . . H20C H 0.4463 1.2631 0.4655 0.067 Uiso 1 1 calc R . . C21 C 0.5801(3) 1.0776(3) 0.59047(19) 0.0302(8) Uani 1 1 d . . . H21 H 0.4875 1.0891 0.5740 0.036 Uiso 1 1 calc R . . C22 C 0.6527(3) 0.9543(3) 0.63644(18) 0.0287(8) Uani 1 1 d . . . H22 H 0.6088 0.8810 0.6512 0.034 Uiso 1 1 calc R . . C23 C 0.9786(3) 0.1868(4) 0.0461(2) 0.0336(8) Uani 1 1 d . . . C24 C 0.8572(4) 0.2898(4) 0.0261(2) 0.0369(9) Uani 1 1 d . . . H24 H 0.8430 0.3428 -0.0238 0.044 Uiso 1 1 calc R . . C25 C 0.7548(3) 0.3165(4) 0.07878(19) 0.0332(8) Uani 1 1 d . . . H25 H 0.6699 0.3875 0.0649 0.040 Uiso 1 1 calc R . . C26 C 0.7752(3) 0.2407(3) 0.15158(18) 0.0249(7) Uani 1 1 d . . . C27 C 0.9017(3) 0.1401(3) 0.17098(19) 0.0284(8) Uani 1 1 d . . . H27 H 0.9184 0.0896 0.2212 0.034 Uiso 1 1 calc R . . C28 C 1.0031(3) 0.1124(3) 0.1187(2) 0.0330(8) Uani 1 1 d . . . H28 H 1.0891 0.0428 0.1324 0.040 Uiso 1 1 calc R . . C29 C 0.6664(3) 0.2688(3) 0.20625(18) 0.0239(7) Uani 1 1 d . . . C30 C 0.4735(3) 0.3929(3) 0.24398(18) 0.0232(7) Uani 1 1 d . . . C31 C 0.3469(3) 0.5074(3) 0.23816(18) 0.0253(7) Uani 1 1 d . . . C32 C 0.3145(3) 0.6110(3) 0.17425(19) 0.0303(8) Uani 1 1 d . . . H32 H 0.3758 0.6083 0.1330 0.036 Uiso 1 1 calc R . . C33 C 0.1940(4) 0.7176(4) 0.1702(2) 0.0388(9) Uani 1 1 d . . . H33 H 0.1719 0.7887 0.1261 0.047 Uiso 1 1 calc R . . C34 C 0.1049(4) 0.7224(4) 0.2295(2) 0.0388(9) Uani 1 1 d . . . H34 H 0.0215 0.7968 0.2265 0.047 Uiso 1 1 calc R . . C35 C 0.1364(3) 0.6195(4) 0.2931(2) 0.0362(9) Uani 1 1 d . . . H35 H 0.0747 0.6229 0.3342 0.043 Uiso 1 1 calc R . . C36 C 0.2565(3) 0.5120(3) 0.29782(19) 0.0300(8) Uani 1 1 d . . . H36 H 0.2776 0.4407 0.3419 0.036 Uiso 1 1 calc R . . C37 C 0.6400(3) 0.2075(3) 0.27682(18) 0.0236(7) Uani 1 1 d . . . C38 C 0.7129(3) 0.0740(3) 0.32453(18) 0.0230(7) Uani 1 1 d . . . C39 C 0.7456(3) 0.0660(3) 0.39810(18) 0.0274(7) Uani 1 1 d . . . H39 H 0.7223 0.1489 0.4173 0.033 Uiso 1 1 calc R . . C40 C 0.8112(3) -0.0597(3) 0.44430(18) 0.0287(8) Uani 1 1 d . . . H40 H 0.8339 -0.0632 0.4946 0.034 Uiso 1 1 calc R . . C41 C 0.8436(3) -0.1806(3) 0.41664(18) 0.0253(7) Uani 1 1 d . . . C42 C 0.9448(4) -0.3209(4) 0.5325(2) 0.0465(10) Uani 1 1 d . . . H42A H 0.9926 -0.4183 0.5551 0.070 Uiso 1 1 calc R . . H42B H 0.8590 -0.2897 0.5599 0.070 Uiso 1 1 calc R . . H42C H 1.0067 -0.2617 0.5348 0.070 Uiso 1 1 calc R . . C43 C 0.8080(3) -0.1741(3) 0.34360(18) 0.0247(7) Uani 1 1 d . . . H43 H 0.8283 -0.2572 0.3247 0.030 Uiso 1 1 calc R . . C44 C 0.7438(3) -0.0489(3) 0.29881(18) 0.0270(7) Uani 1 1 d . . . H44 H 0.7198 -0.0458 0.2488 0.032 Uiso 1 1 calc R . . N1 N 0.9949(3) 0.7290(3) 0.68786(16) 0.0297(7) Uani 1 1 d . . . N2 N 0.5166(2) 0.2901(3) 0.30040(15) 0.0243(6) Uani 1 1 d . . . O1 O 0.9461(2) 0.6173(2) 0.79885(12) 0.0282(5) Uani 1 1 d . . . O2 O 0.5826(2) 1.3097(2) 0.52372(14) 0.0391(6) Uani 1 1 d . . . O3 O 0.5586(2) 0.3878(2) 0.18457(12) 0.0253(5) Uani 1 1 d . . . O4 O 0.9102(2) -0.3105(2) 0.45655(13) 0.0349(6) Uani 1 1 d . . . Cl1 Cl 0.42658(10) 0.84642(11) 1.01894(5) 0.0463(3) Uani 1 1 d . . . Cl2 Cl 1.10289(10) 0.14698(12) -0.02044(6) 0.0521(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0354(18) 0.032(2) 0.027(2) -0.0083(16) 0.0034(15) -0.0134(15) C2 0.0363(19) 0.034(2) 0.035(2) -0.0057(17) -0.0023(16) -0.0026(16) C3 0.0378(19) 0.031(2) 0.029(2) -0.0020(16) -0.0021(15) -0.0008(15) C4 0.0315(17) 0.0229(18) 0.031(2) -0.0075(15) -0.0026(14) -0.0100(14) C5 0.0391(19) 0.0275(19) 0.032(2) 0.0033(16) 0.0025(16) -0.0030(15) C6 0.053(2) 0.031(2) 0.032(2) 0.0016(17) 0.0020(18) -0.0116(18) C7 0.0256(16) 0.0222(17) 0.031(2) -0.0050(15) -0.0041(14) -0.0036(13) C8 0.0265(16) 0.0262(19) 0.033(2) -0.0044(16) -0.0022(15) -0.0080(14) C9 0.0324(18) 0.0245(18) 0.039(2) -0.0109(16) -0.0062(15) -0.0083(14) C10 0.0383(19) 0.030(2) 0.042(2) -0.0052(17) -0.0089(17) -0.0038(16) C11 0.042(2) 0.030(2) 0.060(3) -0.0077(19) -0.016(2) 0.0005(17) C12 0.032(2) 0.028(2) 0.088(4) -0.024(2) -0.018(2) 0.0004(16) C13 0.0303(18) 0.044(2) 0.062(3) -0.027(2) 0.0013(18) -0.0112(17) C14 0.0316(18) 0.032(2) 0.045(2) -0.0136(17) -0.0052(16) -0.0103(15) C15 0.0264(16) 0.0240(18) 0.0285(19) -0.0068(15) -0.0022(13) -0.0077(13) C16 0.0280(16) 0.0285(18) 0.0239(18) -0.0076(14) 0.0026(13) -0.0080(14) C17 0.0261(16) 0.037(2) 0.036(2) -0.0053(16) -0.0008(14) -0.0119(15) C18 0.0348(18) 0.029(2) 0.039(2) 0.0018(16) -0.0030(16) -0.0137(15) C19 0.0318(17) 0.0242(18) 0.0269(19) -0.0031(15) 0.0021(14) -0.0036(14) C20 0.039(2) 0.039(2) 0.046(3) 0.0036(19) -0.0097(18) -0.0031(17) C21 0.0236(16) 0.0308(19) 0.033(2) -0.0030(15) 0.0020(14) -0.0058(14) C22 0.0306(17) 0.0318(19) 0.0261(19) -0.0051(15) 0.0037(14) -0.0141(14) C23 0.0347(18) 0.036(2) 0.034(2) -0.0134(17) 0.0099(15) -0.0139(16) C24 0.041(2) 0.039(2) 0.029(2) -0.0053(17) 0.0049(16) -0.0103(17) C25 0.0320(18) 0.032(2) 0.029(2) 0.0009(16) 0.0023(15) -0.0028(15) C26 0.0285(16) 0.0196(17) 0.0277(19) -0.0037(14) 0.0012(13) -0.0092(13) C27 0.0275(16) 0.0262(18) 0.029(2) 0.0007(15) -0.0024(14) -0.0074(14) C28 0.0273(17) 0.0280(19) 0.044(2) -0.0096(17) 0.0021(15) -0.0067(14) C29 0.0224(15) 0.0203(17) 0.0275(19) -0.0036(14) -0.0033(13) -0.0040(13) C30 0.0227(15) 0.0210(17) 0.0277(19) -0.0071(14) 0.0035(13) -0.0081(13) C31 0.0250(16) 0.0220(17) 0.030(2) -0.0065(14) -0.0018(14) -0.0064(13) C32 0.0314(17) 0.0274(19) 0.028(2) -0.0046(15) 0.0016(14) -0.0025(14) C33 0.0386(19) 0.033(2) 0.036(2) 0.0004(17) -0.0033(17) -0.0004(16) C34 0.0331(18) 0.030(2) 0.046(2) -0.0091(18) 0.0009(17) 0.0049(15) C35 0.0306(18) 0.037(2) 0.037(2) -0.0114(17) 0.0081(15) -0.0010(15) C36 0.0302(17) 0.0294(19) 0.029(2) -0.0061(15) 0.0037(14) -0.0073(14) C37 0.0244(15) 0.0230(17) 0.0250(19) -0.0062(14) -0.0009(13) -0.0081(13) C38 0.0194(15) 0.0219(17) 0.0264(19) -0.0048(14) 0.0015(13) -0.0042(12) C39 0.0312(17) 0.0249(18) 0.0255(19) -0.0068(14) 0.0023(14) -0.0057(14) C40 0.0353(18) 0.0290(19) 0.0182(18) -0.0017(14) -0.0005(14) -0.0053(14) C41 0.0225(15) 0.0203(17) 0.0289(19) -0.0020(14) 0.0035(13) -0.0021(13) C42 0.054(2) 0.039(2) 0.034(2) 0.0025(18) -0.0072(18) 0.0003(18) C43 0.0246(15) 0.0212(17) 0.0292(19) -0.0084(14) 0.0021(13) -0.0058(13) C44 0.0259(16) 0.0284(19) 0.0260(19) -0.0038(15) -0.0009(13) -0.0075(14) N1 0.0255(14) 0.0315(16) 0.0323(17) -0.0100(13) -0.0005(12) -0.0054(12) N2 0.0238(13) 0.0197(14) 0.0295(16) -0.0066(12) 0.0017(11) -0.0052(11) O1 0.0309(12) 0.0224(12) 0.0285(13) -0.0024(10) -0.0027(10) -0.0044(9) O2 0.0404(13) 0.0261(13) 0.0436(16) 0.0076(11) -0.0063(11) -0.0075(11) O3 0.0249(11) 0.0216(12) 0.0267(13) -0.0030(10) 0.0012(9) -0.0036(9) O4 0.0447(14) 0.0246(13) 0.0272(14) 0.0007(10) -0.0049(11) 0.0000(10) Cl1 0.0493(6) 0.0536(7) 0.0380(6) -0.0133(5) 0.0127(4) -0.0164(5) Cl2 0.0429(6) 0.0658(7) 0.0496(7) -0.0228(5) 0.0202(5) -0.0129(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.367(5) . ? C1 C2 1.366(5) . ? C1 Cl1 1.731(4) . ? C2 C3 1.370(5) . ? C2 H2 0.9500 . ? C3 C4 1.383(5) . ? C3 H3 0.9500 . ? C4 C5 1.385(5) . ? C4 C7 1.457(5) . ? C5 C6 1.371(5) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C15 1.351(5) . ? C7 O1 1.368(4) . ? C8 N1 1.291(4) . ? C8 O1 1.346(4) . ? C8 C9 1.445(4) . ? C9 C10 1.380(5) . ? C9 C14 1.390(5) . ? C10 C11 1.370(5) . ? C10 H10 0.9500 . ? C11 C12 1.376(6) . ? C11 H11 0.9500 . ? C12 C13 1.377(6) . ? C12 H12 0.9500 . ? C13 C14 1.372(5) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 N1 1.390(4) . ? C15 C16 1.472(4) . ? C16 C22 1.379(4) . ? C16 C17 1.390(4) . ? C17 C18 1.367(4) . ? C17 H17 0.9500 . ? C18 C19 1.375(4) . ? C18 H18 0.9500 . ? C19 O2 1.361(4) . ? C19 C21 1.380(4) . ? C20 O2 1.419(4) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.380(4) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.366(5) . ? C23 C28 1.376(5) . ? C23 Cl2 1.726(4) . ? C24 C25 1.383(5) . ? C24 H24 0.9500 . ? C25 C26 1.382(5) . ? C25 H25 0.9500 . ? C26 C27 1.388(4) . ? C26 C29 1.453(4) . ? C27 C28 1.373(5) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 C37 1.357(4) . ? C29 O3 1.373(3) . ? C30 N2 1.293(4) . ? C30 O3 1.349(4) . ? C30 C31 1.450(4) . ? C31 C32 1.379(4) . ? C31 C36 1.384(5) . ? C32 C33 1.368(5) . ? C32 H32 0.9500 . ? C33 C34 1.371(5) . ? C33 H33 0.9500 . ? C34 C35 1.371(5) . ? C34 H34 0.9500 . ? C35 C36 1.370(5) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 N2 1.392(4) . ? C37 C38 1.462(4) . ? C38 C44 1.382(4) . ? C38 C39 1.382(4) . ? C39 C40 1.379(4) . ? C39 H39 0.9500 . ? C40 C41 1.382(5) . ? C40 H40 0.9500 . ? C41 O4 1.366(4) . ? C41 C43 1.384(4) . ? C42 O4 1.424(4) . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C43 C44 1.361(4) . ? C43 H43 0.9500 . ? C44 H44 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 C6 C1 C2 120.8(3) . . ? C6 C1 Cl1 119.8(3) . . ? C2 C1 Cl1 119.5(3) . . ? C3 C2 C1 119.7(3) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 121.1(3) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 117.7(3) . . ? C5 C4 C7 120.1(3) . . ? C3 C4 C7 122.1(3) . . ? C4 C5 C6 121.5(3) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C1 C6 C5 119.2(3) . . ? C1 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C15 C7 O1 107.5(3) . . ? C15 C7 C4 137.3(3) . . ? O1 C7 C4 114.9(3) . . ? N1 C8 O1 113.8(3) . . ? N1 C8 C9 128.1(3) . . ? O1 C8 C9 118.1(3) . . ? C10 C9 C14 119.2(3) . . ? C10 C9 C8 121.1(3) . . ? C14 C9 C8 119.6(3) . . ? C11 C10 C9 120.5(4) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 120.2(4) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C13 119.9(3) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C14 C13 C12 120.2(4) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C9 120.1(4) . . ? C13 C14 H14 120.0 . . ? C9 C14 H14 120.0 . . ? C7 C15 N1 108.8(3) . . ? C7 C15 C16 131.4(3) . . ? N1 C15 C16 119.8(3) . . ? C22 C16 C17 117.6(3) . . ? C22 C16 C15 122.3(3) . . ? C17 C16 C15 120.0(3) . . ? C18 C17 C16 121.1(3) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C19 C18 C17 120.2(3) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? O2 C19 C18 115.9(3) . . ? O2 C19 C21 124.1(3) . . ? C18 C19 C21 120.0(3) . . ? O2 C20 H20A 109.5 . . ? O2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 C22 119.0(3) . . ? C19 C21 H21 120.5 . . ? C22 C21 H21 120.5 . . ? C16 C22 C21 121.9(3) . . ? C16 C22 H22 119.1 . . ? C21 C22 H22 119.1 . . ? C24 C23 C28 121.0(3) . . ? C24 C23 Cl2 119.8(3) . . ? C28 C23 Cl2 119.2(3) . . ? C23 C24 C25 119.6(3) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C24 C25 C26 120.5(3) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C27 C26 C25 118.6(3) . . ? C27 C26 C29 121.4(3) . . ? C25 C26 C29 120.0(3) . . ? C28 C27 C26 121.1(3) . . ? C28 C27 H27 119.5 . . ? C26 C27 H27 119.5 . . ? C27 C28 C23 119.1(3) . . ? C27 C28 H28 120.4 . . ? C23 C28 H28 120.4 . . ? C37 C29 O3 107.4(3) . . ? C37 C29 C26 136.7(3) . . ? O3 C29 C26 115.8(3) . . ? N2 C30 O3 113.9(3) . . ? N2 C30 C31 127.6(3) . . ? O3 C30 C31 118.5(3) . . ? C32 C31 C36 119.5(3) . . ? C32 C31 C30 121.3(3) . . ? C36 C31 C30 119.2(3) . . ? C33 C32 C31 120.1(3) . . ? C33 C32 H32 120.0 . . ? C31 C32 H32 120.0 . . ? C32 C33 C34 120.4(3) . . ? C32 C33 H33 119.8 . . ? C34 C33 H33 119.8 . . ? C35 C34 C33 119.8(3) . . ? C35 C34 H34 120.1 . . ? C33 C34 H34 120.1 . . ? C34 C35 C36 120.4(3) . . ? C34 C35 H35 119.8 . . ? C36 C35 H35 119.8 . . ? C31 C36 C35 119.9(3) . . ? C31 C36 H36 120.1 . . ? C35 C36 H36 120.1 . . ? C29 C37 N2 108.7(3) . . ? C29 C37 C38 130.8(3) . . ? N2 C37 C38 120.3(3) . . ? C44 C38 C39 118.0(3) . . ? C44 C38 C37 121.1(3) . . ? C39 C38 C37 120.8(3) . . ? C40 C39 C38 121.4(3) . . ? C40 C39 H39 119.3 . . ? C38 C39 H39 119.3 . . ? C39 C40 C41 119.3(3) . . ? C39 C40 H40 120.4 . . ? C41 C40 H40 120.4 . . ? O4 C41 C43 115.6(3) . . ? O4 C41 C40 124.6(3) . . ? C43 C41 C40 119.7(3) . . ? O4 C42 H42A 109.5 . . ? O4 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? O4 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C44 C43 C41 120.1(3) . . ? C44 C43 H43 120.0 . . ? C41 C43 H43 120.0 . . ? C43 C44 C38 121.4(3) . . ? C43 C44 H44 119.3 . . ? C38 C44 H44 119.3 . . ? C8 N1 C15 104.8(3) . . ? C30 N2 C37 104.9(3) . . ? C8 O1 C7 105.1(2) . . ? C19 O2 C20 118.4(3) . . ? C30 O3 C29 105.0(2) . . ? C41 O4 C42 116.9(3) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.19 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.364 _refine_diff_density_min -0.465 _refine_diff_density_rms 0.097 _database_code_depnum_ccdc_archive 'CCDC 940037' ####################################################################### # # 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_a15034 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H12 F3 N O2' _chemical_formula_sum 'C17 H12 F3 N O2' _chemical_formula_weight 319.28 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.433(2) _cell_length_b 9.695(3) _cell_length_c 17.073(4) _cell_angle_alpha 99.234(5) _cell_angle_beta 94.192(5) _cell_angle_gamma 104.966(5) _cell_volume 1478.2(7) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.53 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9252 _exptl_absorpt_correction_T_max 0.9684 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12247 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0473 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5132 _reflns_number_gt 3440 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0506P)^2^+0.6127P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5132 _refine_ls_number_parameters 427 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0843 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_ref 0.1352 _refine_ls_wR_factor_gt 0.1177 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.022 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8533(3) 0.4145(2) 0.28151(13) 0.0352(6) Uani 1 1 d . . . C2 C 0.7392(3) 0.3067(3) 0.31124(15) 0.0424(6) Uani 1 1 d . . . C3 C 0.8933(2) 0.4373(2) 0.20886(13) 0.0324(5) Uani 1 1 d . . . C4 C 0.8329(2) 0.3593(2) 0.12704(13) 0.0297(5) Uani 1 1 d . . . C5 C 0.6829(2) 0.2911(2) 0.10503(14) 0.0345(6) Uani 1 1 d . . . H5 H 0.6165 0.2907 0.1443 0.041 Uiso 1 1 calc R . . C6 C 0.6291(3) 0.2237(2) 0.02652(13) 0.0339(6) Uani 1 1 d . . . H6 H 0.5266 0.1771 0.0124 0.041 Uiso 1 1 calc R . . C7 C 0.7248(2) 0.2245(2) -0.03083(13) 0.0320(5) Uani 1 1 d . . . C8 C 0.5315(3) 0.0917(3) -0.13420(15) 0.0598(9) Uani 1 1 d . . . H8A H 0.5209 0.0385 -0.1927 0.072 Uiso 1 1 d R . . H8B H 0.4909 0.0309 -0.1016 0.072 Uiso 1 1 d R . . H8C H 0.4566 0.1781 -0.1235 0.072 Uiso 1 1 d R . . C9 C 0.8749(3) 0.2933(2) -0.01007(14) 0.0358(6) Uani 1 1 d . . . H9 H 0.9410 0.2939 -0.0495 0.043 Uiso 1 1 calc R . . C10 C 0.9271(2) 0.3605(2) 0.06774(13) 0.0341(6) Uani 1 1 d . . . H10 H 1.0293 0.4087 0.0814 0.041 Uiso 1 1 calc R . . C11 C 1.0349(3) 0.6102(2) 0.29780(14) 0.0343(6) Uani 1 1 d . . . C12 C 1.1393(3) 0.7424(3) 0.34255(14) 0.0358(6) Uani 1 1 d . . . C13 C 1.2197(3) 0.8424(3) 0.30062(15) 0.0432(6) Uani 1 1 d . . . H13 H 1.2077 0.8230 0.2438 0.052 Uiso 1 1 calc R . . C14 C 1.3172(3) 0.9701(3) 0.34244(17) 0.0507(7) Uani 1 1 d . . . H14 H 1.3716 1.0388 0.3142 0.061 Uiso 1 1 calc R . . C15 C 1.3357(3) 0.9981(3) 0.42497(17) 0.0543(8) Uani 1 1 d . . . H15 H 1.4029 1.0857 0.4533 0.065 Uiso 1 1 calc R . . C16 C 1.2566(3) 0.8989(3) 0.46633(17) 0.0581(8) Uani 1 1 d . . . H16 H 1.2699 0.9183 0.5231 0.070 Uiso 1 1 calc R . . C17 C 1.1584(3) 0.7717(3) 0.42563(15) 0.0478(7) Uani 1 1 d . . . H17 H 1.1037 0.7041 0.4544 0.057 Uiso 1 1 calc R . . C18 C 0.8530(3) 0.9145(2) 0.27980(13) 0.0351(6) Uani 1 1 d . A . C19 C 0.7312(3) 0.8129(3) 0.30897(15) 0.0420(7) Uani 1 1 d . . . C20 C 0.8951(2) 0.9413(2) 0.20787(13) 0.0312(5) Uani 1 1 d . . . C21 C 0.8408(2) 0.8632(2) 0.12542(13) 0.0291(5) Uani 1 1 d . A . C22 C 0.7853(2) 0.7125(2) 0.10539(13) 0.0326(6) Uani 1 1 d . . . H22 H 0.7838 0.6563 0.1462 0.039 Uiso 1 1 calc R A . C23 C 0.7322(2) 0.6427(2) 0.02740(13) 0.0327(6) Uani 1 1 d . A . H23 H 0.6938 0.5400 0.0152 0.039 Uiso 1 1 calc R . . C24 C 0.7357(2) 0.7238(2) -0.03255(13) 0.0307(5) Uani 1 1 d . . . C25 C 0.6224(3) 0.5126(3) -0.13227(15) 0.0536(8) Uani 1 1 d . . . H25A H 0.5528 0.4793 -0.0986 0.064 Uiso 1 1 d R A . H25B H 0.5770 0.4893 -0.1851 0.064 Uiso 1 1 d R . . H25C H 0.7131 0.4651 -0.1198 0.064 Uiso 1 1 d R . . C26 C 0.7940(2) 0.8741(2) -0.01433(13) 0.0336(6) Uani 1 1 d . A . H26 H 0.7981 0.9295 -0.0557 0.040 Uiso 1 1 calc R . . C27 C 0.8460(2) 0.9429(2) 0.06349(13) 0.0326(6) Uani 1 1 d . . . H27 H 0.8857 1.0455 0.0753 0.039 Uiso 1 1 calc R A . C28 C 1.0296(3) 1.1134(2) 0.29919(13) 0.0345(6) Uani 1 1 d . . . C29 C 1.1340(3) 1.2436(3) 0.34646(13) 0.0359(6) Uani 1 1 d . A . C30 C 1.2243(3) 1.3422(3) 0.30784(15) 0.0426(6) Uani 1 1 d . . . H30 H 1.2185 1.3242 0.2512 0.051 Uiso 1 1 calc R A . C31 C 1.3224(3) 1.4665(3) 0.35233(16) 0.0503(7) Uani 1 1 d . A . H31 H 1.3839 1.5338 0.3259 0.060 Uiso 1 1 calc R . . C32 C 1.3316(3) 1.4937(3) 0.43450(16) 0.0508(7) Uani 1 1 d . . . H32 H 1.3991 1.5796 0.4645 0.061 Uiso 1 1 calc R A . C33 C 1.2432(3) 1.3964(3) 0.47304(16) 0.0542(8) Uani 1 1 d . A . H33 H 1.2497 1.4151 0.5297 0.065 Uiso 1 1 calc R . . C34 C 1.1445(3) 1.2710(3) 0.42936(14) 0.0474(7) Uani 1 1 d . . . H34 H 1.0839 1.2038 0.4562 0.057 Uiso 1 1 calc R A . N1 N 1.0116(2) 0.5626(2) 0.22099(11) 0.0346(5) Uani 1 1 d . . . N2 N 1.0087(2) 1.0702(2) 0.22210(11) 0.0342(5) Uani 1 1 d . A . O1 O 0.94220(18) 0.52440(17) 0.33974(9) 0.0383(4) Uani 1 1 d . . . O2 O 0.68370(17) 0.16155(18) -0.10975(9) 0.0416(4) Uani 1 1 d . . . O3 O 0.93812(18) 1.02378(17) 0.33927(9) 0.0382(4) Uani 1 1 d . A . O4 O 0.68424(18) 0.66640(17) -0.11129(9) 0.0415(4) Uani 1 1 d . A . F1 F 0.7817(2) 0.28986(19) 0.38419(9) 0.0736(6) Uani 1 1 d . . . F2 F 0.70576(17) 0.17619(15) 0.26453(9) 0.0561(5) Uani 1 1 d . . . F3 F 0.61311(19) 0.34297(19) 0.31499(12) 0.0807(6) Uani 1 1 d . . . F4 F 0.6331(3) 0.8782(3) 0.3367(2) 0.0665(7) Uani 0.70 1 d P A 1 F5 F 0.7824(3) 0.7701(4) 0.37440(18) 0.0842(10) Uani 0.70 1 d P A 1 F6 F 0.6667(5) 0.6973(4) 0.25740(19) 0.1115(16) Uani 0.70 1 d P A 1 F4' F 0.6020(8) 0.7768(9) 0.2605(5) 0.076(2) Uiso 0.30 1 d P A 2 F5' F 0.7457(8) 0.6879(8) 0.3105(6) 0.0773(19) Uiso 0.30 1 d P A 2 F6' F 0.6925(10) 0.8511(9) 0.3750(5) 0.090(2) Uiso 0.30 1 d P A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0404(14) 0.0298(12) 0.0333(13) 0.0039(10) 0.0015(11) 0.0080(11) C2 0.0470(16) 0.0384(14) 0.0420(15) 0.0082(12) 0.0079(12) 0.0109(13) C3 0.0312(13) 0.0300(12) 0.0377(14) 0.0072(10) 0.0046(10) 0.0109(11) C4 0.0321(13) 0.0247(11) 0.0328(13) 0.0046(10) 0.0039(10) 0.0088(10) C5 0.0300(13) 0.0372(13) 0.0373(14) 0.0112(11) 0.0082(10) 0.0074(11) C6 0.0271(12) 0.0338(13) 0.0390(14) 0.0106(11) 0.0023(10) 0.0034(11) C7 0.0344(13) 0.0281(12) 0.0326(13) 0.0061(10) 0.0025(10) 0.0069(11) C8 0.0454(16) 0.074(2) 0.0381(15) 0.0031(14) -0.0047(12) -0.0159(16) C9 0.0322(13) 0.0360(13) 0.0367(14) 0.0018(11) 0.0090(11) 0.0066(11) C10 0.0263(12) 0.0327(12) 0.0404(14) 0.0031(11) 0.0037(11) 0.0057(11) C11 0.0360(13) 0.0347(13) 0.0344(14) 0.0074(11) 0.0029(11) 0.0130(12) C12 0.0357(13) 0.0348(13) 0.0354(14) 0.0017(11) -0.0007(11) 0.0115(11) C13 0.0410(15) 0.0447(15) 0.0392(14) 0.0002(12) 0.0030(12) 0.0088(13) C14 0.0428(16) 0.0427(15) 0.0599(18) 0.0032(13) 0.0060(13) 0.0040(13) C15 0.0505(17) 0.0415(15) 0.0599(19) -0.0085(14) -0.0090(14) 0.0082(14) C16 0.069(2) 0.0520(17) 0.0428(16) -0.0037(14) -0.0114(15) 0.0113(16) C17 0.0564(17) 0.0451(15) 0.0379(15) 0.0052(12) -0.0032(13) 0.0109(14) C18 0.0409(14) 0.0294(12) 0.0322(13) 0.0024(10) 0.0033(11) 0.0067(11) C19 0.0559(18) 0.0365(14) 0.0322(14) 0.0048(11) 0.0118(13) 0.0097(14) C20 0.0327(13) 0.0276(12) 0.0335(13) 0.0033(10) 0.0036(10) 0.0103(11) C21 0.0263(12) 0.0288(12) 0.0320(12) 0.0036(10) 0.0058(10) 0.0077(10) C22 0.0362(13) 0.0306(12) 0.0329(13) 0.0088(10) 0.0068(10) 0.0099(11) C23 0.0329(13) 0.0271(12) 0.0353(13) 0.0037(10) 0.0057(10) 0.0043(11) C24 0.0258(12) 0.0346(12) 0.0295(13) 0.0023(10) 0.0059(10) 0.0061(11) C25 0.0568(17) 0.0455(16) 0.0377(15) -0.0035(12) 0.0011(13) -0.0146(14) C26 0.0328(13) 0.0331(12) 0.0362(13) 0.0128(11) 0.0059(10) 0.0073(11) C27 0.0313(13) 0.0278(12) 0.0364(13) 0.0055(10) 0.0051(10) 0.0042(11) C28 0.0364(13) 0.0345(13) 0.0319(13) 0.0062(11) 0.0050(10) 0.0083(12) C29 0.0378(14) 0.0343(13) 0.0345(14) 0.0011(11) 0.0010(11) 0.0120(12) C30 0.0436(15) 0.0412(14) 0.0371(14) 0.0002(12) 0.0033(12) 0.0057(13) C31 0.0479(16) 0.0431(15) 0.0509(17) 0.0033(13) 0.0025(13) 0.0009(14) C32 0.0513(17) 0.0401(15) 0.0508(17) -0.0053(13) -0.0094(13) 0.0070(14) C33 0.0671(19) 0.0487(16) 0.0396(15) -0.0023(13) -0.0053(14) 0.0124(16) C34 0.0559(17) 0.0436(15) 0.0368(15) 0.0039(12) 0.0011(13) 0.0068(14) N1 0.0351(11) 0.0336(11) 0.0333(11) 0.0036(9) 0.0016(9) 0.0087(9) N2 0.0348(11) 0.0308(10) 0.0347(11) 0.0038(9) 0.0031(9) 0.0067(9) O1 0.0443(10) 0.0367(9) 0.0322(9) 0.0039(7) 0.0042(8) 0.0098(8) O2 0.0380(9) 0.0459(10) 0.0323(9) -0.0004(8) 0.0011(7) 0.0017(8) O3 0.0467(10) 0.0340(9) 0.0308(9) 0.0036(7) 0.0048(8) 0.0069(8) O4 0.0435(10) 0.0405(10) 0.0318(9) 0.0028(7) 0.0015(8) -0.0008(8) F1 0.0927(13) 0.0732(12) 0.0416(9) 0.0236(8) 0.0062(9) -0.0079(10) F2 0.0682(11) 0.0360(8) 0.0548(10) 0.0060(7) 0.0096(8) -0.0011(8) F3 0.0554(11) 0.0703(12) 0.1322(17) 0.0353(12) 0.0475(11) 0.0250(10) F4 0.0428(13) 0.0653(16) 0.113(2) 0.0394(16) 0.0412(15) 0.0296(13) F5 0.0588(16) 0.119(2) 0.089(2) 0.086(2) 0.0064(14) 0.0099(17) F6 0.131(3) 0.072(2) 0.0633(19) -0.0458(16) 0.063(2) -0.071(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 C1 C3 1.358(3) . ? C1 O1 1.380(3) . ? C1 C2 1.476(3) . ? C2 F1 1.328(3) . ? C2 F3 1.328(3) . ? C2 F2 1.330(3) . ? C3 N1 1.396(3) . ? C3 C4 1.473(3) . ? C4 C5 1.392(3) . ? C4 C10 1.395(3) . ? C5 C6 1.389(3) . ? C5 H5 0.9500 . ? C6 C7 1.379(3) . ? C6 H6 0.9500 . ? C7 O2 1.370(3) . ? C7 C9 1.392(3) . ? C8 O2 1.419(3) . ? C8 H8A 1.0332 . ? C8 H8B 0.9076 . ? C8 H8C 1.2295 . ? C9 C10 1.376(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 N1 1.301(3) . ? C11 O1 1.369(3) . ? C11 C12 1.456(3) . ? C12 C17 1.390(3) . ? C12 C13 1.397(3) . ? C13 C14 1.386(3) . ? C13 H13 0.9500 . ? C14 C15 1.381(4) . ? C14 H14 0.9500 . ? C15 C16 1.380(4) . ? C15 H15 0.9500 . ? C16 C17 1.380(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C20 1.361(3) . ? C18 O3 1.376(3) . ? C18 C19 1.481(3) . ? C19 F6' 1.240(8) . ? C19 F5' 1.258(7) . ? C19 F6 1.286(3) . ? C19 F4 1.323(4) . ? C19 F5 1.352(3) . ? C19 F4' 1.353(7) . ? C20 N2 1.394(3) . ? C20 C21 1.473(3) . ? C21 C22 1.394(3) . ? C21 C27 1.402(3) . ? C22 C23 1.386(3) . ? C22 H22 0.9500 . ? C23 C24 1.384(3) . ? C23 H23 0.9500 . ? C24 O4 1.370(3) . ? C24 C26 1.392(3) . ? C25 O4 1.428(3) . ? C25 H25A 0.9333 . ? C25 H25B 0.9359 . ? C25 H25C 1.0951 . ? C26 C27 1.379(3) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? C28 N2 1.300(3) . ? C28 O3 1.363(3) . ? C28 C29 1.460(3) . ? C29 C34 1.389(3) . ? C29 C30 1.392(3) . ? C30 C31 1.383(3) . ? C30 H30 0.9500 . ? C31 C32 1.377(4) . ? C31 H31 0.9500 . ? C32 C33 1.376(4) . ? C32 H32 0.9500 . ? C33 C34 1.387(3) . ? C33 H33 0.9500 . ? C34 H34 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 C1 O1 108.94(19) . . ? C3 C1 C2 136.0(2) . . ? O1 C1 C2 115.0(2) . . ? F1 C2 F3 106.6(2) . . ? F1 C2 F2 106.8(2) . . ? F3 C2 F2 106.1(2) . . ? F1 C2 C1 112.2(2) . . ? F3 C2 C1 112.6(2) . . ? F2 C2 C1 112.1(2) . . ? C1 C3 N1 107.82(19) . . ? C1 C3 C4 132.2(2) . . ? N1 C3 C4 119.98(19) . . ? C5 C4 C10 118.1(2) . . ? C5 C4 C3 122.6(2) . . ? C10 C4 C3 119.2(2) . . ? C6 C5 C4 121.0(2) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C7 C6 C5 119.8(2) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? O2 C7 C6 124.7(2) . . ? O2 C7 C9 115.3(2) . . ? C6 C7 C9 120.0(2) . . ? O2 C8 H8A 107.9 . . ? O2 C8 H8B 112.9 . . ? H8A C8 H8B 112.0 . . ? O2 C8 H8C 111.2 . . ? H8A C8 H8C 114.0 . . ? H8B C8 H8C 98.7 . . ? C10 C9 C7 119.7(2) . . ? C10 C9 H9 120.1 . . ? C7 C9 H9 120.1 . . ? C9 C10 C4 121.3(2) . . ? C9 C10 H10 119.3 . . ? C4 C10 H10 119.3 . . ? N1 C11 O1 113.46(19) . . ? N1 C11 C12 128.8(2) . . ? O1 C11 C12 117.7(2) . . ? C17 C12 C13 119.7(2) . . ? C17 C12 C11 121.4(2) . . ? C13 C12 C11 118.9(2) . . ? C14 C13 C12 119.5(2) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C15 C14 C13 120.3(3) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C16 C15 C14 120.1(2) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C17 120.3(3) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C16 C17 C12 120.0(3) . . ? C16 C17 H17 120.0 . . ? C12 C17 H17 120.0 . . ? C20 C18 O3 108.87(19) . . ? C20 C18 C19 137.1(2) . . ? O3 C18 C19 113.4(2) . . ? F6' C19 F5' 104.5(6) . . ? F6' C19 F6 126.6(4) . . ? F5' C19 F6 54.3(4) . . ? F6' C19 F4 43.0(4) . . ? F5' C19 F4 131.6(4) . . ? F6 C19 F4 110.4(3) . . ? F6' C19 F5 59.9(5) . . ? F5' C19 F5 55.2(4) . . ? F6 C19 F5 107.2(3) . . ? F4 C19 F5 102.4(3) . . ? F6' C19 F4' 101.8(6) . . ? F5' C19 F4' 99.5(5) . . ? F6 C19 F4' 49.0(3) . . ? F4 C19 F4' 66.0(4) . . ? F5 C19 F4' 136.1(4) . . ? F6' C19 C18 119.0(4) . . ? F5' C19 C18 116.2(4) . . ? F6 C19 C18 114.0(2) . . ? F4 C19 C18 111.7(2) . . ? F5 C19 C18 110.3(2) . . ? F4' C19 C18 113.2(4) . . ? C18 C20 N2 107.71(18) . . ? C18 C20 C21 132.1(2) . . ? N2 C20 C21 120.15(19) . . ? C22 C21 C27 117.9(2) . . ? C22 C21 C20 123.1(2) . . ? C27 C21 C20 119.0(2) . . ? C23 C22 C21 121.6(2) . . ? C23 C22 H22 119.2 . . ? C21 C22 H22 119.2 . . ? C24 C23 C22 119.5(2) . . ? C24 C23 H23 120.3 . . ? C22 C23 H23 120.3 . . ? O4 C24 C23 124.4(2) . . ? O4 C24 C26 115.71(19) . . ? C23 C24 C26 119.9(2) . . ? O4 C25 H25A 111.3 . . ? O4 C25 H25B 108.9 . . ? H25A C25 H25B 109.4 . . ? O4 C25 H25C 105.9 . . ? H25A C25 H25C 105.3 . . ? H25B C25 H25C 116.1 . . ? C27 C26 C24 120.2(2) . . ? C27 C26 H26 119.9 . . ? C24 C26 H26 119.9 . . ? C26 C27 C21 120.8(2) . . ? C26 C27 H27 119.6 . . ? C21 C27 H27 119.6 . . ? N2 C28 O3 113.82(19) . . ? N2 C28 C29 128.7(2) . . ? O3 C28 C29 117.4(2) . . ? C34 C29 C30 119.4(2) . . ? C34 C29 C28 121.1(2) . . ? C30 C29 C28 119.5(2) . . ? C31 C30 C29 119.7(2) . . ? C31 C30 H30 120.1 . . ? C29 C30 H30 120.1 . . ? C32 C31 C30 120.6(3) . . ? C32 C31 H31 119.7 . . ? C30 C31 H31 119.7 . . ? C33 C32 C31 119.9(2) . . ? C33 C32 H32 120.0 . . ? C31 C32 H32 120.0 . . ? C32 C33 C34 120.2(3) . . ? C32 C33 H33 119.9 . . ? C34 C33 H33 119.9 . . ? C33 C34 C29 120.1(2) . . ? C33 C34 H34 119.9 . . ? C29 C34 H34 119.9 . . ? C11 N1 C3 105.79(19) . . ? C28 N2 C20 105.62(18) . . ? C11 O1 C1 103.98(17) . . ? C7 O2 C8 117.53(19) . . ? C28 O3 C18 103.98(17) . . ? C24 O4 C25 117.39(18) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.281 _refine_diff_density_min -0.384 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 940038' ####################################################################### # # 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_15018 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H25 N1 O1' _chemical_formula_sum 'C19 H25 N O' _chemical_formula_weight 283.40 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 monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 6.0403(11) _cell_length_b 7.9754(11) _cell_length_c 17.197(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.530(10) _cell_angle_gamma 90.00 _cell_volume 821.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.146 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9855 _exptl_absorpt_correction_T_max 0.9958 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5410 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0500 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2278 _reflns_number_gt 1962 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0612P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(2) _refine_ls_number_reflns 2278 _refine_ls_number_parameters 190 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1152 _refine_ls_wR_factor_gt 0.0945 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.107 _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 C1 C 0.7245(5) 0.8834(3) -0.00521(14) 0.0291(7) Uani 1 1 d . . . C2 C 0.5614(5) 0.8302(3) -0.07321(15) 0.0287(7) Uani 1 1 d . . . H2 H 0.6285 0.8554 -0.1221 0.034 Uiso 1 1 calc R . . C3 C 0.3411(5) 0.9253(3) -0.07785(16) 0.0328(7) Uani 1 1 d . . . H3A H 0.2776 0.9104 -0.0281 0.039 Uiso 1 1 calc R . . H3B H 0.3691 1.0464 -0.0845 0.039 Uiso 1 1 calc R . . C4 C 0.1728(5) 0.8644(4) -0.14577(17) 0.0393(8) Uani 1 1 d . . . H4A H 0.0289 0.9231 -0.1443 0.047 Uiso 1 1 calc R . . H4B H 0.2275 0.8927 -0.1960 0.047 Uiso 1 1 calc R . . C5 C 0.1355(5) 0.6769(4) -0.14214(19) 0.0420(8) Uani 1 1 d . . . H5A H 0.0331 0.6410 -0.1889 0.050 Uiso 1 1 calc R . . H5B H 0.0643 0.6498 -0.0950 0.050 Uiso 1 1 calc R . . C6 C 0.3560(5) 0.5814(4) -0.13909(17) 0.0402(8) Uani 1 1 d . . . H6A H 0.3283 0.4599 -0.1334 0.048 Uiso 1 1 calc R . . H6B H 0.4190 0.5985 -0.1888 0.048 Uiso 1 1 calc R . . C7 C 0.5237(5) 0.6413(3) -0.07042(15) 0.0332(7) Uani 1 1 d . . . H7A H 0.4681 0.6120 -0.0205 0.040 Uiso 1 1 calc R . . H7B H 0.6677 0.5828 -0.0718 0.040 Uiso 1 1 calc R . . C8 C 0.9631(5) 0.9070(3) 0.09769(14) 0.0277(7) Uani 1 1 d . . . C9 C 1.1169(5) 0.8420(3) 0.16587(14) 0.0279(7) Uani 1 1 d . . . C10 C 1.3202(5) 0.7719(4) 0.15525(17) 0.0397(8) Uani 1 1 d . . . H10 H 1.3629 0.7670 0.1041 0.048 Uiso 1 1 calc R . . C11 C 1.4618(6) 0.7089(4) 0.21806(18) 0.0466(9) Uani 1 1 d . . . H11 H 1.6001 0.6594 0.2100 0.056 Uiso 1 1 calc R . . C12 C 1.4012(6) 0.7184(4) 0.29240(17) 0.0416(9) Uani 1 1 d . . . H12 H 1.4998 0.6779 0.3359 0.050 Uiso 1 1 calc R . . C13 C 1.2005(6) 0.7858(4) 0.30387(16) 0.0419(8) Uani 1 1 d . . . H13 H 1.1589 0.7910 0.3552 0.050 Uiso 1 1 calc R . . C14 C 1.0575(5) 0.8464(4) 0.24077(15) 0.0365(7) Uani 1 1 d . . . H14 H 0.9168 0.8916 0.2490 0.044 Uiso 1 1 calc R . . C15 C 0.9168(5) 1.0653(3) 0.07226(14) 0.0297(7) Uani 1 1 d . . . C16 C 0.9857(5) 1.2410(3) 0.09493(16) 0.0324(7) Uani 1 1 d . . . C17 C 1.1707(6) 1.2405(4) 0.16570(18) 0.0466(9) Uani 1 1 d . . . H17A H 1.2114 1.3562 0.1805 0.070 Uiso 1 1 calc R . . H17B H 1.3020 1.1814 0.1517 0.070 Uiso 1 1 calc R . . H17C H 1.1163 1.1835 0.2100 0.070 Uiso 1 1 calc R . . C18 C 0.7828(6) 1.3388(4) 0.11657(18) 0.0470(9) Uani 1 1 d . . . H18A H 0.8282 1.4535 0.1317 0.071 Uiso 1 1 calc R . . H18B H 0.7249 1.2831 0.1605 0.071 Uiso 1 1 calc R . . H18C H 0.6662 1.3421 0.0712 0.071 Uiso 1 1 calc R . . C19 C 1.0733(6) 1.3281(4) 0.02541(17) 0.0469(9) Uani 1 1 d . . . H19A H 1.1162 1.4436 0.0399 0.070 Uiso 1 1 calc R . . H19B H 0.9560 1.3292 -0.0197 0.070 Uiso 1 1 calc R . . H19C H 1.2036 1.2672 0.0116 0.070 Uiso 1 1 calc R . . N1 N 0.8400(4) 0.7919(3) 0.04703(13) 0.0309(5) Uani 1 1 d . . . O1 O 0.7593(3) 1.0517(2) 0.00560(10) 0.0319(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0283(17) 0.0259(15) 0.0333(14) -0.0008(12) 0.0045(12) -0.0044(14) C2 0.0275(17) 0.0315(16) 0.0273(13) 0.0013(12) 0.0041(11) -0.0021(14) C3 0.0311(18) 0.0291(16) 0.0376(15) 0.0028(12) 0.0027(13) 0.0033(14) C4 0.032(2) 0.0383(19) 0.0453(16) 0.0077(13) -0.0014(14) -0.0018(15) C5 0.032(2) 0.042(2) 0.0490(17) 0.0025(14) -0.0039(14) -0.0077(17) C6 0.036(2) 0.0369(19) 0.0455(17) -0.0065(13) -0.0022(15) -0.0069(15) C7 0.0282(19) 0.0300(16) 0.0405(15) -0.0033(13) 0.0009(13) -0.0028(15) C8 0.0276(17) 0.0289(16) 0.0266(13) -0.0001(11) 0.0032(11) -0.0016(13) C9 0.0280(18) 0.0241(16) 0.0310(14) 0.0015(11) 0.0020(12) 0.0010(14) C10 0.038(2) 0.047(2) 0.0354(15) 0.0008(13) 0.0075(13) 0.0074(17) C11 0.037(2) 0.051(2) 0.0500(18) -0.0006(15) -0.0006(15) 0.0191(17) C12 0.045(2) 0.0392(19) 0.0362(16) -0.0002(13) -0.0100(15) 0.0107(17) C13 0.053(2) 0.0437(19) 0.0294(15) 0.0016(12) 0.0072(14) 0.0101(18) C14 0.0359(19) 0.0403(19) 0.0337(15) 0.0000(13) 0.0062(13) 0.0087(15) C15 0.0293(18) 0.0315(16) 0.0270(14) 0.0007(11) -0.0014(12) -0.0001(14) C16 0.0370(19) 0.0259(16) 0.0327(14) -0.0004(12) -0.0018(13) -0.0030(14) C17 0.050(2) 0.0371(19) 0.0482(18) -0.0012(14) -0.0112(16) -0.0089(16) C18 0.050(2) 0.0358(19) 0.0560(19) -0.0064(13) 0.0098(17) 0.0018(17) C19 0.060(2) 0.0368(18) 0.0448(17) -0.0002(13) 0.0117(16) -0.0122(18) N1 0.0292(14) 0.0306(12) 0.0316(11) 0.0020(10) -0.0014(9) 0.0010(12) O1 0.0344(12) 0.0268(11) 0.0319(9) 0.0025(7) -0.0055(8) -0.0033(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 C1 N1 1.289(3) . ? C1 O1 1.368(3) . ? C1 C2 1.489(3) . ? C2 C3 1.525(4) . ? C2 C7 1.525(4) . ? C2 H2 1.0000 . ? C3 C4 1.524(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.515(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.529(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.528(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C15 1.353(4) . ? C8 N1 1.409(3) . ? C8 C9 1.490(3) . ? C9 C14 1.382(4) . ? C9 C10 1.383(4) . ? C10 C11 1.382(4) . ? C10 H10 0.9500 . ? C11 C12 1.377(5) . ? C11 H11 0.9500 . ? C12 C13 1.364(4) . ? C12 H12 0.9500 . ? C13 C14 1.383(4) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 O1 1.395(3) . ? C15 C16 1.499(4) . ? C16 C19 1.535(4) . ? C16 C18 1.539(5) . ? C16 C17 1.540(4) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? 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 N1 C1 O1 113.7(2) . . ? N1 C1 C2 128.9(2) . . ? O1 C1 C2 117.4(2) . . ? C1 C2 C3 112.5(2) . . ? C1 C2 C7 110.1(2) . . ? C3 C2 C7 111.1(2) . . ? C1 C2 H2 107.7 . . ? C3 C2 H2 107.7 . . ? C7 C2 H2 107.7 . . ? C4 C3 C2 111.8(2) . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3A 109.2 . . ? C4 C3 H3B 109.2 . . ? C2 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C5 C4 C3 111.8(2) . . ? C5 C4 H4A 109.3 . . ? C3 C4 H4A 109.3 . . ? C5 C4 H4B 109.3 . . ? C3 C4 H4B 109.3 . . ? H4A C4 H4B 107.9 . . ? C4 C5 C6 111.1(3) . . ? C4 C5 H5A 109.4 . . ? C6 C5 H5A 109.4 . . ? C4 C5 H5B 109.4 . . ? C6 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? C7 C6 C5 110.9(2) . . ? C7 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? C7 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.0 . . ? C2 C7 C6 111.8(2) . . ? C2 C7 H7A 109.3 . . ? C6 C7 H7A 109.3 . . ? C2 C7 H7B 109.3 . . ? C6 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? C15 C8 N1 109.8(2) . . ? C15 C8 C9 131.3(2) . . ? N1 C8 C9 119.0(2) . . ? C14 C9 C10 118.5(2) . . ? C14 C9 C8 120.9(3) . . ? C10 C9 C8 120.6(2) . . ? C11 C10 C9 120.9(3) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C12 C11 C10 119.5(3) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C13 C12 C11 120.4(3) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 120.0(3) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C9 C14 C13 120.7(3) . . ? C9 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C8 C15 O1 106.5(2) . . ? C8 C15 C16 138.6(2) . . ? O1 C15 C16 115.0(2) . . ? C15 C16 C19 109.4(2) . . ? C15 C16 C18 109.5(2) . . ? C19 C16 C18 109.0(2) . . ? C15 C16 C17 110.5(2) . . ? C19 C16 C17 109.2(3) . . ? C18 C16 C17 109.2(2) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C1 N1 C8 104.8(2) . . ? C1 O1 C15 105.3(2) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.155 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 940042'