# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_2d _database_code_depnum_ccdc_archive 'CCDC 900474' #TrackingRef 'strukil_etal_all_in_one_f.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H12 F N O' _chemical_formula_sum 'C17 H12 F N O' _chemical_formula_weight 265.28 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' _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.0689(2) _cell_length_b 10.5607(5) _cell_length_c 12.7211(6) _cell_angle_alpha 71.230(5) _cell_angle_beta 80.914(4) _cell_angle_gamma 82.591(4) _cell_volume 634.45(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150 _cell_measurement_reflns_used 4449 _cell_measurement_theta_min 4.2192 _cell_measurement_theta_max 28.3165 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_T_min 0.86154 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.3426 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6925 _diffrn_reflns_av_R_equivalents 0.0200 _diffrn_reflns_av_sigmaI/netI 0.0194 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.23 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2216 _reflns_number_gt 1921 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0480P)^2^+0.1383P] 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 2216 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0918 _refine_ls_wR_factor_gt 0.0876 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 0.3395(2) 0.23345(12) 0.46122(10) 0.0213(3) Uani 1 1 d . . . C2 C 0.3014(2) 0.32204(12) 0.34580(10) 0.0219(3) Uani 1 1 d . . . C3 C 0.1410(2) 0.28587(13) 0.28448(11) 0.0249(3) Uani 1 1 d . . . H3 H 0.0473 0.2075 0.3178 0.030 Uiso 1 1 calc R . . C4 C 0.1132(3) 0.36297(14) 0.17326(11) 0.0287(3) Uani 1 1 d . . . H4 H 0.0036 0.3357 0.1317 0.034 Uiso 1 1 calc R . . C5 C 0.2435(3) 0.47685(14) 0.12490(11) 0.0290(3) Uani 1 1 d . . . H5 H 0.2245 0.5281 0.0496 0.035 Uiso 1 1 calc R . . C6 C 0.4066(2) 0.51969(13) 0.18530(11) 0.0254(3) Uani 1 1 d . . . C7 C 0.5392(3) 0.63942(13) 0.13602(11) 0.0302(3) Uani 1 1 d . . . H7 H 0.5191 0.6915 0.0610 0.036 Uiso 1 1 calc R . . C8 C 0.6949(3) 0.68052(14) 0.19501(12) 0.0319(3) Uani 1 1 d . . . H8 H 0.7838 0.7603 0.1609 0.038 Uiso 1 1 calc R . . C9 C 0.7234(3) 0.60453(13) 0.30647(11) 0.0296(3) Uani 1 1 d . . . H9 H 0.8305 0.6341 0.3474 0.036 Uiso 1 1 calc R . . C10 C 0.5995(2) 0.48892(13) 0.35668(11) 0.0249(3) Uani 1 1 d . . . H10 H 0.6211 0.4392 0.4321 0.030 Uiso 1 1 calc R . . C11 C 0.4388(2) 0.44205(12) 0.29748(10) 0.0221(3) Uani 1 1 d . . . C12 C 0.1032(2) 0.09939(12) 0.63871(10) 0.0223(3) Uani 1 1 d . . . C13 C 0.3053(2) 0.00007(12) 0.67665(11) 0.0253(3) Uani 1 1 d . . . H13 H 0.4583 -0.0133 0.6265 0.030 Uiso 1 1 calc R . . C14 C 0.2836(3) -0.07932(13) 0.78751(11) 0.0288(3) Uani 1 1 d . . . H14 H 0.4209 -0.1472 0.8142 0.035 Uiso 1 1 calc R . . C15 C 0.0599(3) -0.05815(13) 0.85822(11) 0.0285(3) Uani 1 1 d . . . C16 C -0.1438(3) 0.03855(14) 0.82356(11) 0.0295(3) Uani 1 1 d . . . H16 H -0.2966 0.0507 0.8743 0.035 Uiso 1 1 calc R . . C17 C -0.1207(2) 0.11795(13) 0.71265(11) 0.0269(3) Uani 1 1 d . . . H17 H -0.2590 0.1857 0.6869 0.032 Uiso 1 1 calc R . . N1 N 0.11512(19) 0.18306(10) 0.52608(8) 0.0231(3) Uani 1 1 d . . . H1 H -0.0355 0.2040 0.4958 0.028 Uiso 1 1 calc R . . O1 O 0.56083(16) 0.20717(9) 0.49528(7) 0.0282(2) Uani 1 1 d . . . F1 F 0.03917(18) -0.13724(9) 0.96699(6) 0.0419(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 0.0200(6) 0.0217(6) 0.0237(6) -0.0082(5) -0.0033(5) -0.0030(5) C2 0.0175(6) 0.0243(6) 0.0228(6) -0.0074(5) -0.0005(5) 0.0000(5) C3 0.0220(6) 0.0247(6) 0.0280(7) -0.0074(5) -0.0037(5) -0.0024(5) C4 0.0281(7) 0.0335(7) 0.0271(7) -0.0115(6) -0.0087(5) -0.0007(6) C5 0.0307(7) 0.0318(7) 0.0210(7) -0.0046(6) -0.0051(5) 0.0023(6) C6 0.0233(6) 0.0254(7) 0.0247(7) -0.0069(5) 0.0006(5) 0.0016(5) C7 0.0325(7) 0.0256(7) 0.0257(7) -0.0022(6) 0.0019(6) 0.0002(5) C8 0.0311(7) 0.0237(7) 0.0374(8) -0.0072(6) 0.0045(6) -0.0064(5) C9 0.0292(7) 0.0279(7) 0.0341(8) -0.0132(6) -0.0004(6) -0.0058(5) C10 0.0244(6) 0.0259(7) 0.0244(7) -0.0085(5) -0.0010(5) -0.0020(5) C11 0.0190(6) 0.0226(6) 0.0235(7) -0.0081(5) 0.0004(5) 0.0011(5) C12 0.0210(6) 0.0239(6) 0.0231(7) -0.0061(5) -0.0042(5) -0.0072(5) C13 0.0242(6) 0.0224(6) 0.0281(7) -0.0062(5) -0.0009(5) -0.0048(5) C14 0.0302(7) 0.0228(7) 0.0323(8) -0.0042(6) -0.0085(6) -0.0037(5) C15 0.0370(7) 0.0277(7) 0.0207(7) -0.0029(5) -0.0057(6) -0.0115(6) C16 0.0282(7) 0.0355(7) 0.0253(7) -0.0099(6) 0.0008(5) -0.0085(6) C17 0.0219(6) 0.0298(7) 0.0287(7) -0.0077(6) -0.0036(5) -0.0042(5) N1 0.0168(5) 0.0276(6) 0.0233(6) -0.0039(5) -0.0049(4) -0.0036(4) O1 0.0201(5) 0.0336(5) 0.0272(5) -0.0021(4) -0.0055(4) -0.0049(4) F1 0.0553(5) 0.0405(5) 0.0233(4) 0.0011(4) -0.0043(4) -0.0092(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.2325(18) . ? C1 N1 1.3546(18) . ? C1 C2 1.4924(17) . ? C2 C3 1.3740(18) . ? C2 C11 1.4353(18) . ? C3 C4 1.4059(19) . ? C3 H3 0.9500 . ? C4 C5 1.364(2) . ? C4 H4 0.9500 . ? C5 C6 1.414(2) . ? C5 H5 0.9500 . ? C6 C7 1.421(2) . ? C6 C11 1.4217(18) . ? C7 C8 1.363(2) . ? C7 H7 0.9500 . ? C8 C9 1.406(2) . ? C8 H8 0.9500 . ? C9 C10 1.3646(19) . ? C9 H9 0.9500 . ? C10 C11 1.4191(19) . ? C10 H10 0.9500 . ? C12 C17 1.3913(19) . ? C12 C13 1.3913(19) . ? C12 N1 1.4174(16) . ? C13 C14 1.3848(19) . ? C13 H13 0.9500 . ? C14 C15 1.374(2) . ? C14 H14 0.9500 . ? C15 F1 1.3624(15) . ? C15 C16 1.373(2) . ? C16 C17 1.3854(19) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? N1 H1 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 O1 C1 N1 122.08(12) . . ? O1 C1 C2 122.27(11) . . ? N1 C1 C2 115.65(11) . . ? C3 C2 C11 120.05(12) . . ? C3 C2 C1 119.65(11) . . ? C11 C2 C1 120.27(11) . . ? C2 C3 C4 121.08(12) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 120.09(12) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 120.94(12) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C6 C7 121.21(12) . . ? C5 C6 C11 119.62(12) . . ? C7 C6 C11 119.18(12) . . ? C8 C7 C6 120.88(13) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C9 119.84(12) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C10 C9 C8 121.01(12) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 120.74(12) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C10 C11 C6 118.33(12) . . ? C10 C11 C2 123.44(12) . . ? C6 C11 C2 118.21(11) . . ? C17 C12 C13 119.61(12) . . ? C17 C12 N1 118.07(11) . . ? C13 C12 N1 122.31(11) . . ? C14 C13 C12 120.06(12) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C15 C14 C13 118.77(12) . . ? C15 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? F1 C15 C16 118.84(12) . . ? F1 C15 C14 118.43(12) . . ? C16 C15 C14 122.73(13) . . ? C15 C16 C17 118.25(12) . . ? C15 C16 H16 120.9 . . ? C17 C16 H16 120.9 . . ? C16 C17 C12 120.57(12) . . ? C16 C17 H17 119.7 . . ? C12 C17 H17 119.7 . . ? C1 N1 C12 125.31(10) . . ? C1 N1 H1 117.3 . . ? C12 N1 H1 117.3 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.156 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.037 data_2e _database_code_depnum_ccdc_archive 'CCDC 900475' #TrackingRef 'strukil_etal_all_in_one_f.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H12 Cl N O' _chemical_formula_sum 'C17 H12 Cl N O' _chemical_formula_weight 281.73 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' _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.04782(18) _cell_length_b 10.7197(4) _cell_length_c 13.3908(6) _cell_angle_alpha 71.589(4) _cell_angle_beta 80.789(3) _cell_angle_gamma 82.637(3) _cell_volume 676.30(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150 _cell_measurement_reflns_used 6275 _cell_measurement_theta_min 4.2071 _cell_measurement_theta_max 28.5249 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_absorpt_coefficient_mu 0.276 _exptl_absorpt_correction_T_min 0.94328 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_detector_area_resol_mean 16.3426 _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7477 _diffrn_reflns_av_R_equivalents 0.0138 _diffrn_reflns_av_sigmaI/netI 0.0142 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.22 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2358 _reflns_number_gt 2174 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0442P)^2^+0.2109P] 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 2358 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0307 _refine_ls_R_factor_gt 0.0280 _refine_ls_wR_factor_ref 0.0803 _refine_ls_wR_factor_gt 0.0784 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 0.3426(2) 0.73285(12) -0.03718(10) 0.0185(3) Uani 1 1 d . . . C2 C 0.3046(2) 0.82136(12) -0.14640(10) 0.0187(3) Uani 1 1 d . . . C3 C 0.1440(3) 0.78663(13) -0.20560(10) 0.0224(3) Uani 1 1 d . . . H3 H 0.0492 0.7096 -0.1750 0.027 Uiso 1 1 calc R . . C4 C 0.1180(3) 0.86343(14) -0.31070(11) 0.0260(3) Uani 1 1 d . . . H4 H 0.0074 0.8377 -0.3507 0.031 Uiso 1 1 calc R . . C5 C 0.2512(3) 0.97482(14) -0.35554(10) 0.0266(3) Uani 1 1 d . . . H5 H 0.2349 1.0251 -0.4271 0.032 Uiso 1 1 calc R . . C6 C 0.4136(2) 1.01653(13) -0.29682(10) 0.0224(3) Uani 1 1 d . . . C7 C 0.5444(3) 1.13478(14) -0.34130(11) 0.0275(3) Uani 1 1 d . . . H7 H 0.5265 1.1863 -0.4124 0.033 Uiso 1 1 calc R . . C8 C 0.6956(3) 1.17580(13) -0.28360(11) 0.0286(3) Uani 1 1 d . . . H8 H 0.7820 1.2553 -0.3145 0.034 Uiso 1 1 calc R . . C9 C 0.7233(3) 1.10011(13) -0.17826(11) 0.0262(3) Uani 1 1 d . . . H9 H 0.8277 1.1294 -0.1382 0.031 Uiso 1 1 calc R . . C10 C 0.6020(3) 0.98510(13) -0.13281(10) 0.0220(3) Uani 1 1 d . . . H10 H 0.6242 0.9351 -0.0617 0.026 Uiso 1 1 calc R . . C11 C 0.4430(2) 0.93908(12) -0.19044(10) 0.0191(3) Uani 1 1 d . . . C12 C 0.1047(2) 0.60070(12) 0.13048(10) 0.0192(3) Uani 1 1 d . . . C13 C 0.3073(3) 0.50261(13) 0.16539(11) 0.0228(3) Uani 1 1 d . . . H13 H 0.4605 0.4893 0.1174 0.027 Uiso 1 1 calc R . . C14 C 0.2852(3) 0.42439(13) 0.27039(11) 0.0247(3) Uani 1 1 d . . . H14 H 0.4233 0.3575 0.2946 0.030 Uiso 1 1 calc R . . C15 C 0.0616(3) 0.44412(13) 0.33955(10) 0.0238(3) Uani 1 1 d . . . C16 C -0.1423(3) 0.54051(14) 0.30619(10) 0.0250(3) Uani 1 1 d . . . H16 H -0.2955 0.5529 0.3545 0.030 Uiso 1 1 calc R . . C17 C -0.1200(3) 0.61875(13) 0.20138(10) 0.0232(3) Uani 1 1 d . . . H17 H -0.2591 0.6853 0.1776 0.028 Uiso 1 1 calc R . . N1 N 0.1163(2) 0.68333(11) 0.02391(8) 0.0202(2) Uani 1 1 d . . . H1 H -0.0348 0.7040 -0.0047 0.024 Uiso 1 1 calc R . . O1 O 0.56460(17) 0.70656(9) -0.00511(7) 0.0247(2) Uani 1 1 d . . . Cl1 Cl 0.03591(8) 0.34425(3) 0.47123(3) 0.03528(14) 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 0.0167(6) 0.0194(6) 0.0205(6) -0.0071(5) -0.0025(5) -0.0020(5) C2 0.0142(6) 0.0211(6) 0.0198(6) -0.0063(5) -0.0009(5) 0.0011(5) C3 0.0182(6) 0.0242(7) 0.0250(7) -0.0074(5) -0.0039(5) -0.0011(5) C4 0.0250(7) 0.0314(7) 0.0244(7) -0.0104(6) -0.0092(5) 0.0000(6) C5 0.0274(7) 0.0307(7) 0.0189(7) -0.0039(6) -0.0064(5) 0.0023(6) C6 0.0191(6) 0.0238(7) 0.0215(7) -0.0054(5) -0.0009(5) 0.0022(5) C7 0.0273(7) 0.0257(7) 0.0231(7) -0.0004(6) -0.0008(5) 0.0000(6) C8 0.0281(7) 0.0217(7) 0.0331(8) -0.0056(6) 0.0024(6) -0.0060(6) C9 0.0257(7) 0.0271(7) 0.0284(7) -0.0121(6) -0.0011(5) -0.0052(6) C10 0.0211(6) 0.0240(7) 0.0206(6) -0.0076(5) -0.0009(5) -0.0011(5) C11 0.0156(6) 0.0212(6) 0.0194(6) -0.0068(5) -0.0002(5) 0.0016(5) C12 0.0174(6) 0.0210(6) 0.0205(6) -0.0055(5) -0.0040(5) -0.0062(5) C13 0.0204(6) 0.0210(6) 0.0260(7) -0.0059(5) -0.0009(5) -0.0040(5) C14 0.0264(7) 0.0191(6) 0.0277(7) -0.0036(5) -0.0076(5) -0.0021(5) C15 0.0319(7) 0.0212(7) 0.0196(7) -0.0040(5) -0.0063(5) -0.0090(5) C16 0.0230(7) 0.0313(7) 0.0218(7) -0.0090(6) -0.0005(5) -0.0059(6) C17 0.0182(6) 0.0276(7) 0.0237(7) -0.0065(6) -0.0047(5) -0.0020(5) N1 0.0140(5) 0.0249(6) 0.0198(5) -0.0024(4) -0.0043(4) -0.0030(4) O1 0.0153(5) 0.0302(5) 0.0248(5) -0.0007(4) -0.0054(4) -0.0042(4) Cl1 0.0533(3) 0.0299(2) 0.01929(19) -0.00131(14) -0.00538(15) -0.00580(16) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.2316(15) . ? C1 N1 1.3555(16) . ? C1 C2 1.4975(17) . ? C2 C3 1.3764(18) . ? C2 C11 1.4325(18) . ? C3 C4 1.4055(19) . ? C3 H3 0.9500 . ? C4 C5 1.364(2) . ? C4 H4 0.9500 . ? C5 C6 1.4189(19) . ? C5 H5 0.9500 . ? C6 C7 1.4175(19) . ? C6 C11 1.4247(18) . ? C7 C8 1.365(2) . ? C7 H7 0.9500 . ? C8 C9 1.407(2) . ? C8 H8 0.9500 . ? C9 C10 1.3657(19) . ? C9 H9 0.9500 . ? C10 C11 1.4227(18) . ? C10 H10 0.9500 . ? C12 C13 1.3918(18) . ? C12 C17 1.3933(18) . ? C12 N1 1.4187(16) . ? C13 C14 1.3862(19) . ? C13 H13 0.9500 . ? C14 C15 1.380(2) . ? C14 H14 0.9500 . ? C15 C16 1.382(2) . ? C15 Cl1 1.7442(13) . ? C16 C17 1.3841(18) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? N1 H1 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 O1 C1 N1 122.24(11) . . ? O1 C1 C2 122.23(11) . . ? N1 C1 C2 115.53(10) . . ? C3 C2 C11 120.21(12) . . ? C3 C2 C1 119.67(11) . . ? C11 C2 C1 120.08(11) . . ? C2 C3 C4 120.95(12) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 120.22(12) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.91(12) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C7 C6 C5 121.36(12) . . ? C7 C6 C11 119.23(12) . . ? C5 C6 C11 119.41(12) . . ? C8 C7 C6 121.06(13) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C9 119.86(12) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C10 C9 C8 120.84(12) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 120.93(12) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C10 C11 C6 118.07(12) . . ? C10 C11 C2 123.62(11) . . ? C6 C11 C2 118.28(11) . . ? C13 C12 C17 119.60(12) . . ? C13 C12 N1 122.30(11) . . ? C17 C12 N1 118.10(11) . . ? C14 C13 C12 119.88(12) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C15 C14 C13 119.68(12) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C16 121.26(12) . . ? C14 C15 Cl1 119.12(10) . . ? C16 C15 Cl1 119.62(11) . . ? C15 C16 C17 119.07(12) . . ? C15 C16 H16 120.5 . . ? C17 C16 H16 120.5 . . ? C16 C17 C12 120.51(12) . . ? C16 C17 H17 119.7 . . ? C12 C17 H17 119.7 . . ? C1 N1 C12 124.95(10) . . ? C1 N1 H1 117.5 . . ? C12 N1 H1 117.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.192 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.045 data_4 _database_code_depnum_ccdc_archive 'CCDC 900476' #TrackingRef 'strukil_etal_all_in_one_f.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H16 N2 O2' _chemical_formula_sum 'C16 H16 N2 O2' _chemical_formula_weight 268.31 _chemical_compound_source 'chemical synthesis' 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 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_int_tables_number 15 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 17.179(4) _cell_length_b 5.0906(7) _cell_length_c 29.764(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.721(19) _cell_angle_gamma 90.00 _cell_volume 2601.7(9) _cell_formula_units_Z 8 _cell_measurement_temperature 293 _cell_measurement_reflns_used 1441 _cell_measurement_theta_min 4.1529 _cell_measurement_theta_max 26.3797 loop_ _cell_oxdiff_twin_id _cell_oxdiff_twin_matrix_11 _cell_oxdiff_twin_matrix_12 _cell_oxdiff_twin_matrix_13 _cell_oxdiff_twin_matrix_21 _cell_oxdiff_twin_matrix_22 _cell_oxdiff_twin_matrix_23 _cell_oxdiff_twin_matrix_31 _cell_oxdiff_twin_matrix_32 _cell_oxdiff_twin_matrix_33 1 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000 1.0000 2 -0.9931 0.0065 -0.0005 -0.0003 -0.9939 -0.0001 0.1118 0.0084 0.9949 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_T_min 0.73655 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_method '\w scans' _diffrn_radiation_collimation '1.0 mm' _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_detector_area_resol_mean 16.3426 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2626 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1918 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 4.18 _diffrn_reflns_theta_max 24.99 _diffrn_orient_matrix_UB_11 -0.0160875000 _diffrn_orient_matrix_UB_12 -0.0637132000 _diffrn_orient_matrix_UB_13 -0.0192357000 _diffrn_orient_matrix_UB_21 0.0377323000 _diffrn_orient_matrix_UB_22 -0.0169109000 _diffrn_orient_matrix_UB_23 -0.0083515000 _diffrn_orient_matrix_UB_31 0.0032801000 _diffrn_orient_matrix_UB_32 -0.1224925000 _diffrn_orient_matrix_UB_33 0.0111552000 loop_ _diffrn_oxdiff_twin_id _diffrn_oxdiff_twin_ratio _diffrn_oxdiff_twin_reflns_isolated _diffrn_oxdiff_twin_reflns_overlapped 1 0.6841 175 6343 2 0.3159 171 6343 _reflns_number_total 2626 _reflns_number_gt 1421 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_structure_solution SIR-2004 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1661P)^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_number_reflns 2626 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1720 _refine_ls_R_factor_gt 0.1129 _refine_ls_wR_factor_ref 0.3593 _refine_ls_wR_factor_gt 0.3349 _refine_ls_goodness_of_fit_ref 1.145 _refine_ls_restrained_S_all 1.145 _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 0.2442(4) 0.2270(10) 0.39591(19) 0.0506(18) Uani 1 1 d . . . O2 O 0.3857(4) 0.7222(10) 0.52167(19) 0.0480(17) Uani 1 1 d . . . N2 N 0.4182(3) 0.2931(12) 0.5353(2) 0.0326(16) Uani 1 1 d . . . H2 H 0.4109 0.1356 0.5256 0.039 Uiso 1 1 calc R . . N1 N 0.2255(4) 0.6600(12) 0.3784(2) 0.0358(16) Uani 1 1 d . . . H1 H 0.2314 0.8171 0.3885 0.043 Uiso 1 1 calc R . . C6 C 0.1358(5) 0.4437(17) 0.3251(3) 0.042(2) Uani 1 1 d . . . H6 H 0.1233 0.3191 0.3466 0.051 Uiso 1 1 calc R . . C2 C 0.2939(4) 0.5517(15) 0.4466(3) 0.0321(18) Uani 1 1 d . . . H2A H 0.3305 0.6850 0.4374 0.039 Uiso 1 1 calc R . . H2B H 0.2562 0.6396 0.4650 0.039 Uiso 1 1 calc R . . C12 C 0.5251(4) 0.1260(17) 0.5806(3) 0.041(2) Uani 1 1 d . . . H12 H 0.5290 -0.0129 0.5605 0.049 Uiso 1 1 calc R . . C5 C 0.1895(4) 0.6344(14) 0.3351(2) 0.0272(17) Uani 1 1 d . . . C4 C 0.3804(5) 0.4857(14) 0.5123(2) 0.0319(19) Uani 1 1 d . . . C16 C 0.4612(5) 0.5237(17) 0.6036(3) 0.040(2) Uani 1 1 d . . . H16 H 0.4236 0.6529 0.5987 0.048 Uiso 1 1 calc R . . C14 C 0.5669(5) 0.3422(19) 0.6484(3) 0.052(3) Uani 1 1 d . . . H14 H 0.5994 0.3475 0.6739 0.062 Uiso 1 1 calc R . . C10 C 0.2083(5) 0.8236(16) 0.3039(3) 0.043(2) Uani 1 1 d . . . H10 H 0.2439 0.9557 0.3111 0.051 Uiso 1 1 calc R . . C3 C 0.3325(4) 0.3911(15) 0.4731(2) 0.0326(18) Uani 1 1 d . . . H3A H 0.3670 0.2912 0.4543 0.039 Uiso 1 1 calc R . . H3B H 0.2951 0.2675 0.4846 0.039 Uiso 1 1 calc R . . C11 C 0.4686(4) 0.3211(15) 0.5737(3) 0.0338(19) Uani 1 1 d . . . C15 C 0.5113(5) 0.5332(19) 0.6417(3) 0.047(2) Uani 1 1 d . . . H15 H 0.5068 0.6687 0.6625 0.057 Uiso 1 1 calc R . . C9 C 0.1721(5) 0.8106(18) 0.2614(3) 0.049(2) Uani 1 1 d . . . H9 H 0.1842 0.9340 0.2396 0.059 Uiso 1 1 calc R . . C7 C 0.1002(5) 0.4377(18) 0.2828(3) 0.051(2) Uani 1 1 d . . . H7 H 0.0632 0.3093 0.2759 0.061 Uiso 1 1 calc R . . C13 C 0.5747(5) 0.1429(17) 0.6176(3) 0.046(2) Uani 1 1 d . . . H13 H 0.6140 0.0187 0.6218 0.055 Uiso 1 1 calc R . . C1 C 0.2514(5) 0.4631(14) 0.4053(2) 0.0341(19) Uani 1 1 d . . . C8 C 0.1187(5) 0.6158(19) 0.2514(3) 0.051(2) Uani 1 1 d . . . H8 H 0.0953 0.6074 0.2229 0.061 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 0.070(4) 0.022(3) 0.058(4) 0.001(3) -0.028(3) 0.003(3) O2 0.071(4) 0.026(3) 0.045(3) -0.003(3) -0.027(3) -0.001(3) N2 0.036(4) 0.021(3) 0.040(4) -0.002(3) -0.015(3) -0.003(3) N1 0.051(4) 0.019(3) 0.036(4) 0.001(3) -0.015(3) -0.001(3) C6 0.039(5) 0.035(4) 0.053(5) 0.009(4) -0.012(4) -0.007(4) C2 0.031(4) 0.029(4) 0.036(4) -0.001(4) -0.005(3) -0.006(4) C12 0.036(5) 0.038(5) 0.049(5) 0.003(4) -0.003(4) 0.002(4) C5 0.034(4) 0.026(4) 0.021(3) -0.004(3) -0.009(3) 0.008(3) C4 0.041(5) 0.024(4) 0.030(4) 0.002(3) -0.012(3) 0.000(4) C16 0.040(5) 0.038(5) 0.041(5) -0.004(4) -0.010(4) 0.001(4) C14 0.050(5) 0.055(6) 0.049(5) 0.017(5) -0.026(4) -0.015(5) C10 0.049(5) 0.034(5) 0.045(5) -0.001(4) -0.009(4) -0.006(4) C3 0.037(4) 0.029(4) 0.031(4) 0.006(3) -0.006(3) -0.004(4) C11 0.032(4) 0.027(4) 0.042(4) 0.002(4) -0.011(3) -0.005(4) C15 0.052(6) 0.047(5) 0.042(5) 0.000(4) -0.017(4) -0.012(5) C9 0.063(6) 0.047(5) 0.036(5) 0.011(4) -0.005(4) 0.008(5) C7 0.057(6) 0.041(5) 0.054(5) -0.003(5) -0.032(4) 0.000(5) C13 0.042(5) 0.042(5) 0.053(5) 0.016(5) -0.015(4) -0.001(5) C1 0.045(5) 0.023(4) 0.034(4) -0.003(3) -0.011(4) 0.001(4) C8 0.056(6) 0.055(6) 0.041(5) -0.010(5) -0.026(4) 0.016(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.239(9) . ? O2 C4 1.239(9) . ? N2 C4 1.351(9) . ? N2 C11 1.419(9) . ? N2 H2 0.8600 . ? N1 C1 1.351(9) . ? N1 C5 1.419(9) . ? N1 H1 0.8600 . ? C6 C5 1.365(10) . ? C6 C7 1.386(11) . ? C6 H6 0.9300 . ? C2 C3 1.302(10) . ? C2 C1 1.481(10) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C12 C13 1.375(10) . ? C12 C11 1.399(10) . ? C12 H12 0.9300 . ? C5 C10 1.382(10) . ? C4 C3 1.488(10) . ? C16 C11 1.371(11) . ? C16 C15 1.405(10) . ? C16 H16 0.9300 . ? C14 C15 1.372(12) . ? C14 C13 1.377(13) . ? C14 H14 0.9300 . ? C10 C9 1.395(11) . ? C10 H10 0.9300 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C15 H15 0.9300 . ? C9 C8 1.377(12) . ? C9 H9 0.9300 . ? C7 C8 1.345(13) . ? C7 H7 0.9300 . ? C13 H13 0.9300 . ? C8 H8 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 N2 C11 127.4(6) . . ? C4 N2 H2 116.3 . . ? C11 N2 H2 116.3 . . ? C1 N1 C5 126.8(6) . . ? C1 N1 H1 116.6 . . ? C5 N1 H1 116.6 . . ? C5 C6 C7 119.3(8) . . ? C5 C6 H6 120.3 . . ? C7 C6 H6 120.3 . . ? C3 C2 C1 122.7(7) . . ? C3 C2 H2A 106.7 . . ? C1 C2 H2A 106.7 . . ? C3 C2 H2B 106.7 . . ? C1 C2 H2B 106.7 . . ? H2A C2 H2B 106.6 . . ? C13 C12 C11 118.9(8) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C6 C5 C10 121.3(7) . . ? C6 C5 N1 122.4(7) . . ? C10 C5 N1 116.2(7) . . ? O2 C4 N2 124.1(7) . . ? O2 C4 C3 121.7(7) . . ? N2 C4 C3 114.1(6) . . ? C11 C16 C15 119.0(8) . . ? C11 C16 H16 120.5 . . ? C15 C16 H16 120.5 . . ? C15 C14 C13 120.6(7) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C5 C10 C9 118.0(7) . . ? C5 C10 H10 121.0 . . ? C9 C10 H10 121.0 . . ? C2 C3 C4 122.0(7) . . ? C2 C3 H3A 106.8 . . ? C4 C3 H3A 106.8 . . ? C2 C3 H3B 106.8 . . ? C4 C3 H3B 106.8 . . ? H3A C3 H3B 106.7 . . ? C16 C11 C12 121.1(7) . . ? C16 C11 N2 122.1(7) . . ? C12 C11 N2 116.8(7) . . ? C14 C15 C16 119.9(9) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C8 C9 C10 120.3(8) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C8 C7 C6 120.6(8) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C12 C13 C14 120.5(8) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? O1 C1 N1 123.8(7) . . ? O1 C1 C2 121.8(7) . . ? N1 C1 C2 114.3(6) . . ? C7 C8 C9 120.4(8) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.379 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.101