# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_2011nb0068 _audit_creation_method SHELXL-97 _chemical_compound_source 'Cally J E Haynes' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H20 N2 O S' _chemical_formula_sum 'C14 H20 N2 O S' _chemical_formula_weight 264.38 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' S S 0.1246 0.1234 '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/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 3.9805(12) _cell_length_b 21.132(7) _cell_length_c 16.710(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.391(4) _cell_angle_gamma 90.00 _cell_volume 1396.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2574 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.223 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8874 _exptl_absorpt_correction_T_max 0.9978 _exptl_absorpt_process_details ; Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.475 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_source 'Rotating Anode' _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_collimation 'Confocal mirrors, VHF Varimax ' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 (Right)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen micromount' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6301 _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 27.52 _reflns_number_total 3169 _reflns_number_gt 2815 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'WINGX (Farrugia, 1998)' _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^)+(0.0400P)^2^+0.2733P] 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 3169 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0459 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.0871 _refine_ls_wR_factor_gt 0.0834 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 0.3298(3) 0.66357(6) 0.41258(8) 0.0141(3) Uani 1 1 d . . . C2 C 0.4866(3) 0.71985(6) 0.39348(9) 0.0174(3) Uani 1 1 d . . . H2A H 0.5672 0.7485 0.4350 0.021 Uiso 1 1 calc R . . C3 C 0.5245(4) 0.73381(7) 0.31428(9) 0.0211(3) Uani 1 1 d . . . H3 H 0.6354 0.7717 0.3016 0.025 Uiso 1 1 calc R . . C4 C 0.4018(4) 0.69284(7) 0.25298(9) 0.0221(3) Uani 1 1 d . . . H4 H 0.4266 0.7029 0.1985 0.027 Uiso 1 1 calc R . . C5 C 0.2429(4) 0.63727(7) 0.27160(9) 0.0203(3) Uani 1 1 d . . . H5 H 0.1583 0.6092 0.2297 0.024 Uiso 1 1 calc R . . C6 C 0.2068(3) 0.62237(6) 0.35091(8) 0.0160(3) Uani 1 1 d . . . H6 H 0.0983 0.5841 0.3633 0.019 Uiso 1 1 calc R . . C7 C 0.2823(3) 0.64882(6) 0.49748(8) 0.0146(3) Uani 1 1 d . . . C8 C 0.2626(3) 0.55125(6) 0.58443(8) 0.0143(3) Uani 1 1 d . . . C9 C 0.0645(4) 0.54826(7) 0.71684(8) 0.0162(3) Uani 1 1 d . . . H9A H 0.2674 0.5243 0.7391 0.019 Uiso 1 1 calc R . . H9B H -0.1227 0.5178 0.7040 0.019 Uiso 1 1 calc R . . C10 C -0.0313(3) 0.59571(6) 0.77863(8) 0.0156(3) Uani 1 1 d . . . H10A H -0.2467 0.6164 0.7579 0.019 Uiso 1 1 calc R . . H10B H 0.1450 0.6289 0.7862 0.019 Uiso 1 1 calc R . . C11 C -0.0708(3) 0.56537(6) 0.85985(8) 0.0154(3) Uani 1 1 d . . . H11A H 0.1449 0.5448 0.8806 0.018 Uiso 1 1 calc R . . H11B H -0.2463 0.5321 0.8522 0.018 Uiso 1 1 calc R . . C12 C -0.1684(3) 0.61265(7) 0.92223(8) 0.0153(3) Uani 1 1 d . . . H12A H 0.0050 0.6464 0.9292 0.018 Uiso 1 1 calc R . . H12B H -0.3861 0.6327 0.9019 0.018 Uiso 1 1 calc R . . C13 C -0.2020(3) 0.58264(6) 1.00389(8) 0.0161(3) Uani 1 1 d . . . H13A H -0.3716 0.5483 0.9967 0.019 Uiso 1 1 calc R . . H13B H 0.0172 0.5635 1.0248 0.019 Uiso 1 1 calc R . . C14 C -0.3070(4) 0.62952(7) 1.06580(8) 0.0192(3) Uani 1 1 d . . . H14A H -0.3214 0.6076 1.1170 0.029 Uiso 1 1 calc R . . H14B H -0.5280 0.6476 1.0465 0.029 Uiso 1 1 calc R . . H14C H -0.1390 0.6635 1.0737 0.029 Uiso 1 1 calc R . . N1 N 0.3241(3) 0.58633(5) 0.51604(7) 0.0141(2) Uani 1 1 d . . . H1 H 0.4044 0.5637 0.4782 0.017 Uiso 1 1 calc R . . N2 N 0.1335(3) 0.58128(5) 0.64403(7) 0.0169(3) Uani 1 1 d . . . H2 H 0.0889 0.6220 0.6393 0.020 Uiso 1 1 calc R . . O1 O 0.3292(3) 0.49419(4) 0.58583(6) 0.0179(2) Uani 1 1 d . . . S1 S 0.18284(9) 0.705677(16) 0.55904(2) 0.01934(11) 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 0.0138(6) 0.0152(6) 0.0138(7) 0.0004(5) 0.0029(5) 0.0029(5) C2 0.0200(7) 0.0142(7) 0.0184(7) 0.0001(5) 0.0033(5) 0.0011(5) C3 0.0241(7) 0.0159(7) 0.0244(8) 0.0036(6) 0.0070(6) 0.0023(6) C4 0.0277(8) 0.0238(8) 0.0158(7) 0.0050(6) 0.0062(6) 0.0073(6) C5 0.0238(7) 0.0213(7) 0.0154(7) -0.0018(6) 0.0010(6) 0.0034(6) C6 0.0180(6) 0.0138(6) 0.0164(7) 0.0005(5) 0.0028(5) 0.0009(5) C7 0.0130(6) 0.0147(6) 0.0159(7) -0.0011(5) 0.0010(5) -0.0003(5) C8 0.0147(6) 0.0158(7) 0.0124(7) -0.0005(5) 0.0018(5) -0.0003(5) C9 0.0204(7) 0.0155(6) 0.0135(7) -0.0001(5) 0.0052(5) -0.0001(6) C10 0.0172(6) 0.0163(7) 0.0138(7) -0.0019(5) 0.0044(5) 0.0004(5) C11 0.0162(6) 0.0159(6) 0.0147(7) 0.0000(5) 0.0045(5) 0.0005(5) C12 0.0167(6) 0.0160(6) 0.0138(7) -0.0010(5) 0.0040(5) -0.0011(5) C13 0.0177(6) 0.0172(7) 0.0140(7) -0.0001(5) 0.0040(5) -0.0007(5) C14 0.0215(7) 0.0217(7) 0.0148(7) -0.0032(6) 0.0044(5) -0.0004(6) N1 0.0193(6) 0.0125(5) 0.0112(6) -0.0019(4) 0.0051(4) 0.0017(5) N2 0.0234(6) 0.0137(6) 0.0145(6) 0.0005(5) 0.0065(5) 0.0034(5) O1 0.0256(5) 0.0140(5) 0.0153(5) 0.0010(4) 0.0075(4) 0.0034(4) S1 0.0292(2) 0.01272(17) 0.01696(19) -0.00249(13) 0.00650(14) 0.00181(14) _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 C6 1.3955(19) . ? C1 C2 1.396(2) . ? C1 C7 1.4851(19) . ? C2 C3 1.381(2) . ? C2 H2A 0.9500 . ? C3 C4 1.388(2) . ? C3 H3 0.9500 . ? C4 C5 1.385(2) . ? C4 H4 0.9500 . ? C5 C6 1.385(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 N1 1.3624(17) . ? C7 S1 1.6581(14) . ? C8 O1 1.2342(17) . ? C8 N2 1.3315(17) . ? C8 N1 1.4062(17) . ? C9 N2 1.4549(18) . ? C9 C10 1.5180(19) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.5248(19) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.5250(19) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.5240(19) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.5239(19) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? N1 H1 0.8800 . ? N2 H2 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 C6 C1 C2 119.45(13) . . ? C6 C1 C7 120.19(12) . . ? C2 C1 C7 120.31(12) . . ? C3 C2 C1 120.03(13) . . ? C3 C2 H2A 120.0 . . ? C1 C2 H2A 120.0 . . ? C2 C3 C4 120.47(14) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 119.68(14) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C6 C5 C4 120.40(14) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C1 119.96(13) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? N1 C7 C1 113.31(11) . . ? N1 C7 S1 126.34(11) . . ? C1 C7 S1 120.35(10) . . ? O1 C8 N2 123.46(13) . . ? O1 C8 N1 118.30(12) . . ? N2 C8 N1 118.23(12) . . ? N2 C9 C10 109.70(11) . . ? N2 C9 H9A 109.7 . . ? C10 C9 H9A 109.7 . . ? N2 C9 H9B 109.7 . . ? C10 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? C9 C10 C11 112.72(11) . . ? C9 C10 H10A 109.0 . . ? C11 C10 H10A 109.0 . . ? C9 C10 H10B 109.0 . . ? C11 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? C10 C11 C12 113.10(12) . . ? C10 C11 H11A 109.0 . . ? C12 C11 H11A 109.0 . . ? C10 C11 H11B 109.0 . . ? C12 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? C13 C12 C11 113.19(12) . . ? C13 C12 H12A 108.9 . . ? C11 C12 H12A 108.9 . . ? C13 C12 H12B 108.9 . . ? C11 C12 H12B 108.9 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C12 113.29(12) . . ? C14 C13 H13A 108.9 . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13B 108.9 . . ? C12 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C7 N1 C8 131.93(12) . . ? C7 N1 H1 114.0 . . ? C8 N1 H1 114.0 . . ? C8 N2 C9 121.43(12) . . ? C8 N2 H2 119.3 . . ? C9 N2 H2 119.3 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 S1 0.88 2.28 3.0046(15) 140.2 . N1 H1 O1 0.88 2.01 2.8672(15) 166.0 3_666 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.354 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 941594' ####################################################################### # # 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_2011nb0069 _audit_creation_method SHELXL-97 _chemical_compound_source 'Cally-Jo Elizabeth Haynes' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H19 F3 N2 O S' _chemical_formula_sum 'C15 H19 F3 N2 O S' _chemical_formula_weight 332.39 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' S S 0.1246 0.1234 '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_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6713(7) _cell_length_b 12.2170(9) _cell_length_c 14.0933(11) _cell_angle_alpha 95.844(7) _cell_angle_beta 92.324(7) _cell_angle_gamma 104.975(7) _cell_volume 1596.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 11455 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.236 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.689 _exptl_absorpt_process_details ; Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.475 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_source 'Rotating Anode' _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_collimation 'Confocal mirrors, VHF Varimax ' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 (Right)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen micromount' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14983 _diffrn_reflns_av_R_equivalents 0.0383 _diffrn_reflns_av_sigmaI/netI 0.0549 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.48 _reflns_number_total 7217 _reflns_number_gt 5172 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'WINGX (Farrugia, 1998)' _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^)+(0.0570P)^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 7217 _refine_ls_number_parameters 397 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0626 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1175 _refine_ls_wR_factor_gt 0.1086 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 S1 S 0.06180(5) 0.41848(3) 0.37999(3) 0.02206(12) Uani 1 1 d . . . S2 S -0.45241(5) 0.43158(3) 0.36674(3) 0.02222(12) Uani 1 1 d . . . O2 O -0.10115(14) 0.76311(10) 0.40947(9) 0.0299(3) Uani 1 1 d . . . F6 F -0.14012(12) 1.17572(8) 0.76164(8) 0.0402(3) Uani 1 1 d . . . F5 F -0.34983(12) 1.08169(9) 0.79272(9) 0.0394(3) Uani 1 1 d . . . F1 F 0.36278(13) 1.03917(9) 0.86565(7) 0.0390(3) Uani 1 1 d . . . F2 F 0.17344(12) 1.07411(9) 0.80926(8) 0.0380(3) Uani 1 1 d . . . F4 F -0.16341(15) 1.05028(10) 0.85946(8) 0.0463(3) Uani 1 1 d . . . O1 O 0.37007(14) 0.77067(10) 0.39652(9) 0.0302(3) Uani 1 1 d . . . C18 C 0.33614(18) 1.01677(13) 0.61401(12) 0.0222(4) Uani 1 1 d . . . H18 H 0.3680 1.0959 0.6078 0.027 Uiso 1 1 calc R . . C4 C -0.33745(18) 0.81725(13) 0.58900(11) 0.0195(3) Uani 1 1 d . . . H4 H -0.4226 0.7604 0.5659 0.023 Uiso 1 1 calc R . . F3 F 0.37850(14) 1.17053(8) 0.77384(9) 0.0457(3) Uani 1 1 d . . . N1 N 0.18903(15) 0.63440(10) 0.44774(9) 0.0179(3) Uani 1 1 d . . . H1 H 0.1290 0.6207 0.4931 0.022 Uiso 1 1 calc R . . C21 C 0.24392(17) 0.78459(13) 0.63213(11) 0.0186(3) Uani 1 1 d . . . H21 H 0.2138 0.7054 0.6385 0.022 Uiso 1 1 calc R . . C3 C -0.34126(18) 0.89796(13) 0.66488(12) 0.0198(3) Uani 1 1 d . . . H3 H -0.4279 0.8951 0.6952 0.024 Uiso 1 1 calc R . . C22 C 0.25068(18) 0.86438(13) 0.71081(12) 0.0203(4) Uani 1 1 d . . . H22 H 0.2234 0.8399 0.7708 0.024 Uiso 1 1 calc R . . C7 C -0.09007(18) 0.98638(14) 0.65303(12) 0.0237(4) Uani 1 1 d . . . H7 H -0.0059 1.0451 0.6744 0.028 Uiso 1 1 calc R . . N4 N -0.22577(15) 0.57084(11) 0.30396(10) 0.0211(3) Uani 1 1 d . . . H4A H -0.1607 0.6369 0.3102 0.025 Uiso 1 1 calc R . . C19 C 0.32781(18) 0.93662(13) 0.53569(12) 0.0219(4) Uani 1 1 d . . . H19 H 0.3543 0.9612 0.4756 0.026 Uiso 1 1 calc R . . N2 N 0.25934(15) 0.56832(11) 0.30240(9) 0.0198(3) Uani 1 1 d . . . H2 H 0.3154 0.6378 0.3030 0.024 Uiso 1 1 calc R . . C5 C -0.21023(18) 0.81897(12) 0.54661(11) 0.0183(3) Uani 1 1 d . . . N3 N -0.30615(15) 0.63760(11) 0.44524(10) 0.0188(3) Uani 1 1 d . . . H3A H -0.3728 0.6265 0.4866 0.023 Uiso 1 1 calc R . . C2 C -0.21772(19) 0.98275(13) 0.69614(12) 0.0202(4) Uani 1 1 d . . . C6 C -0.08632(18) 0.90387(13) 0.57878(12) 0.0222(4) Uani 1 1 d . . . H6 H 0.0010 0.9053 0.5498 0.027 Uiso 1 1 calc R . . C30 C 0.5033(2) 0.80515(15) -0.10021(13) 0.0299(4) Uani 1 1 d . . . H30A H 0.4735 0.8629 -0.1334 0.045 Uiso 1 1 calc R . . H30B H 0.5102 0.7421 -0.1470 0.045 Uiso 1 1 calc R . . H30C H 0.5970 0.8394 -0.0657 0.045 Uiso 1 1 calc R . . C8 C -0.19998(18) 0.73788(13) 0.46179(12) 0.0201(4) Uani 1 1 d . . . C1 C -0.2187(2) 1.07203(14) 0.77692(13) 0.0269(4) Uani 1 1 d . . . C16 C 0.30360(19) 1.06562(14) 0.78711(13) 0.0248(4) Uani 1 1 d . . . C11 C -0.11824(19) 0.54407(14) 0.15221(12) 0.0215(4) Uani 1 1 d . . . H11A H -0.1054 0.4839 0.1034 0.026 Uiso 1 1 calc R . . H11B H -0.0241 0.5791 0.1877 0.026 Uiso 1 1 calc R . . C17 C 0.29740(17) 0.98031(13) 0.70185(12) 0.0193(3) Uani 1 1 d . . . C20 C 0.28115(17) 0.82044(13) 0.54388(11) 0.0183(3) Uani 1 1 d . . . C13 C -0.06350(18) 0.68038(13) 0.02582(12) 0.0215(4) Uani 1 1 d . . . H13A H 0.0335 0.7161 0.0570 0.026 Uiso 1 1 calc R . . H13B H -0.0566 0.6154 -0.0202 0.026 Uiso 1 1 calc R . . C26 C 0.36913(18) 0.53576(14) 0.15235(12) 0.0216(4) Uani 1 1 d . . . H26A H 0.3814 0.4740 0.1049 0.026 Uiso 1 1 calc R . . H26B H 0.4630 0.5705 0.1882 0.026 Uiso 1 1 calc R . . C24 C 0.17735(17) 0.54605(13) 0.37423(11) 0.0174(3) Uani 1 1 d . . . C27 C 0.32713(18) 0.62604(14) 0.09908(12) 0.0216(4) Uani 1 1 d . . . H27A H 0.3223 0.6909 0.1458 0.026 Uiso 1 1 calc R . . H27B H 0.2303 0.5933 0.0667 0.026 Uiso 1 1 calc R . . C28 C 0.43190(18) 0.67000(13) 0.02505(11) 0.0212(4) Uani 1 1 d . . . H28A H 0.5286 0.7024 0.0577 0.025 Uiso 1 1 calc R . . H28B H 0.4368 0.6048 -0.0213 0.025 Uiso 1 1 calc R . . C12 C -0.16353(19) 0.63491(13) 0.10156(12) 0.0217(4) Uani 1 1 d . . . H12A H -0.2616 0.6022 0.0711 0.026 Uiso 1 1 calc R . . H12B H -0.1667 0.6991 0.1496 0.026 Uiso 1 1 calc R . . C23 C 0.28434(18) 0.74032(13) 0.45662(12) 0.0199(4) Uani 1 1 d . . . C15 C -0.0078(2) 0.81131(15) -0.10400(13) 0.0333(5) Uani 1 1 d . . . H15A H -0.0432 0.8665 -0.1371 0.050 Uiso 1 1 calc R . . H15B H -0.0018 0.7475 -0.1503 0.050 Uiso 1 1 calc R . . H15C H 0.0877 0.8485 -0.0729 0.050 Uiso 1 1 calc R . . C29 C 0.39306(19) 0.76023(14) -0.02956(12) 0.0244(4) Uani 1 1 d . . . H29A H 0.3849 0.8246 0.0166 0.029 Uiso 1 1 calc R . . H29B H 0.2983 0.7272 -0.0647 0.029 Uiso 1 1 calc R . . C25 C 0.26200(19) 0.48365(13) 0.22167(11) 0.0211(4) Uani 1 1 d . . . H25A H 0.1652 0.4556 0.1883 0.025 Uiso 1 1 calc R . . H25B H 0.2887 0.4179 0.2454 0.025 Uiso 1 1 calc R . . C9 C -0.31969(18) 0.55143(13) 0.36983(11) 0.0184(3) Uani 1 1 d . . . C10 C -0.22372(19) 0.48892(13) 0.22137(12) 0.0220(4) Uani 1 1 d . . . H10A H -0.3209 0.4613 0.1886 0.026 Uiso 1 1 calc R . . H10B H -0.1958 0.4225 0.2429 0.026 Uiso 1 1 calc R . . C14 C -0.1101(2) 0.76699(14) -0.02900(12) 0.0270(4) Uani 1 1 d . . . H14A H -0.1171 0.8321 0.0167 0.032 Uiso 1 1 calc R . . H14B H -0.2068 0.7314 -0.0608 0.032 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 S1 0.0276(2) 0.0146(2) 0.0209(2) -0.00120(16) 0.00360(18) 0.00101(16) S2 0.0274(2) 0.0155(2) 0.0209(2) -0.00136(16) 0.00241(18) 0.00180(16) O2 0.0326(8) 0.0231(6) 0.0274(7) -0.0050(5) 0.0115(6) -0.0031(5) F6 0.0479(7) 0.0186(5) 0.0458(7) -0.0102(5) 0.0103(6) -0.0017(5) F5 0.0332(6) 0.0347(6) 0.0463(7) -0.0178(5) 0.0063(5) 0.0099(5) F1 0.0523(8) 0.0428(6) 0.0234(6) -0.0130(5) -0.0137(5) 0.0242(5) F2 0.0307(6) 0.0456(7) 0.0362(7) -0.0183(5) -0.0018(5) 0.0171(5) F4 0.0736(9) 0.0451(7) 0.0219(6) -0.0098(5) -0.0101(6) 0.0262(6) O1 0.0359(8) 0.0244(6) 0.0224(7) -0.0040(5) 0.0111(6) -0.0049(5) C18 0.0261(9) 0.0145(8) 0.0248(9) 0.0022(7) -0.0022(7) 0.0036(6) C4 0.0234(9) 0.0133(7) 0.0203(8) 0.0022(6) 0.0010(7) 0.0020(6) F3 0.0647(9) 0.0194(6) 0.0414(7) -0.0106(5) 0.0111(6) -0.0052(5) N1 0.0216(7) 0.0167(7) 0.0142(7) -0.0006(5) 0.0029(6) 0.0036(5) C21 0.0194(8) 0.0145(7) 0.0206(8) 0.0025(6) 0.0005(7) 0.0020(6) C3 0.0228(9) 0.0164(8) 0.0204(8) 0.0028(6) 0.0055(7) 0.0048(6) C22 0.0221(9) 0.0203(8) 0.0165(8) 0.0004(6) 0.0009(7) 0.0026(7) C7 0.0220(9) 0.0213(8) 0.0244(9) -0.0029(7) -0.0019(7) 0.0023(7) N4 0.0282(8) 0.0154(7) 0.0172(7) -0.0009(5) 0.0039(6) 0.0020(6) C19 0.0264(9) 0.0180(8) 0.0192(8) 0.0033(6) -0.0001(7) 0.0021(7) N2 0.0243(8) 0.0168(7) 0.0165(7) -0.0013(5) 0.0029(6) 0.0029(5) C5 0.0239(9) 0.0147(8) 0.0160(8) 0.0012(6) 0.0023(7) 0.0049(6) N3 0.0212(7) 0.0166(7) 0.0180(7) 0.0003(5) 0.0049(6) 0.0042(5) C2 0.0273(9) 0.0150(8) 0.0180(8) 0.0002(6) -0.0005(7) 0.0062(6) C6 0.0195(9) 0.0215(8) 0.0238(9) -0.0005(7) 0.0020(7) 0.0033(7) C30 0.0336(11) 0.0279(9) 0.0289(10) 0.0070(8) 0.0030(8) 0.0079(8) C8 0.0233(9) 0.0167(8) 0.0195(8) 0.0006(6) 0.0021(7) 0.0040(6) C1 0.0304(10) 0.0228(9) 0.0267(10) -0.0026(7) 0.0020(8) 0.0074(7) C16 0.0276(10) 0.0198(8) 0.0247(9) -0.0037(7) -0.0020(8) 0.0051(7) C11 0.0266(9) 0.0222(8) 0.0178(8) -0.0015(6) 0.0021(7) 0.0115(7) C17 0.0191(8) 0.0167(8) 0.0207(9) -0.0035(6) -0.0023(7) 0.0047(6) C20 0.0183(8) 0.0171(8) 0.0181(8) 0.0001(6) 0.0010(7) 0.0033(6) C13 0.0229(9) 0.0212(8) 0.0206(9) -0.0005(7) 0.0016(7) 0.0075(7) C26 0.0247(9) 0.0241(8) 0.0181(8) -0.0002(7) 0.0032(7) 0.0110(7) C24 0.0164(8) 0.0182(8) 0.0173(8) -0.0007(6) -0.0021(6) 0.0057(6) C27 0.0249(9) 0.0222(8) 0.0189(8) -0.0013(6) 0.0020(7) 0.0098(7) C28 0.0238(9) 0.0220(8) 0.0185(8) -0.0015(6) 0.0018(7) 0.0087(7) C12 0.0250(9) 0.0203(8) 0.0215(9) 0.0008(7) 0.0030(7) 0.0092(7) C23 0.0242(9) 0.0167(8) 0.0167(8) 0.0002(6) 0.0003(7) 0.0023(7) C15 0.0432(12) 0.0283(10) 0.0303(10) 0.0096(8) 0.0093(9) 0.0097(9) C29 0.0270(10) 0.0237(9) 0.0239(9) 0.0015(7) 0.0013(8) 0.0100(7) C25 0.0259(9) 0.0173(8) 0.0190(8) -0.0036(6) 0.0007(7) 0.0060(7) C9 0.0237(9) 0.0155(7) 0.0165(8) 0.0002(6) -0.0025(7) 0.0074(6) C10 0.0322(10) 0.0159(8) 0.0183(8) -0.0007(6) 0.0031(7) 0.0078(7) C14 0.0351(11) 0.0245(9) 0.0248(9) 0.0061(7) 0.0066(8) 0.0120(8) _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 S1 C24 1.6786(16) . ? S2 C9 1.6747(16) . ? O2 C8 1.2263(19) . ? F6 C1 1.342(2) . ? F5 C1 1.329(2) . ? F1 C16 1.332(2) . ? F2 C16 1.336(2) . ? F4 C1 1.340(2) . ? O1 C23 1.2265(19) . ? C18 C19 1.384(2) . ? C18 C17 1.391(2) . ? C18 H18 0.9500 . ? C4 C5 1.386(2) . ? C4 C3 1.387(2) . ? C4 H4 0.9500 . ? F3 C16 1.3351(19) . ? N1 C23 1.372(2) . ? N1 C24 1.3967(19) . ? N1 H1 0.8800 . ? C21 C22 1.387(2) . ? C21 C20 1.391(2) . ? C21 H21 0.9500 . ? C3 C2 1.385(2) . ? C3 H3 0.9500 . ? C22 C17 1.392(2) . ? C22 H22 0.9500 . ? C7 C6 1.386(2) . ? C7 C2 1.390(2) . ? C7 H7 0.9500 . ? N4 C9 1.321(2) . ? N4 C10 1.4601(19) . ? N4 H4A 0.8800 . ? C19 C20 1.392(2) . ? C19 H19 0.9500 . ? N2 C24 1.318(2) . ? N2 C25 1.4634(19) . ? N2 H2 0.8800 . ? C5 C6 1.391(2) . ? C5 C8 1.496(2) . ? N3 C8 1.372(2) . ? N3 C9 1.394(2) . ? N3 H3A 0.8800 . ? C2 C1 1.496(2) . ? C6 H6 0.9500 . ? C30 C29 1.525(2) . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C16 C17 1.497(2) . ? C11 C10 1.518(2) . ? C11 C12 1.523(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C20 C23 1.498(2) . ? C13 C14 1.518(2) . ? C13 C12 1.520(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C26 C25 1.517(2) . ? C26 C27 1.523(2) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.524(2) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.520(2) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C15 C14 1.521(2) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? 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 C19 C18 C17 119.35(15) . . ? C19 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? C5 C4 C3 120.42(15) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C23 N1 C24 126.74(14) . . ? C23 N1 H1 116.6 . . ? C24 N1 H1 116.6 . . ? C22 C21 C20 120.03(14) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C2 C3 C4 119.48(16) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C21 C22 C17 119.98(15) . . ? C21 C22 H22 120.0 . . ? C17 C22 H22 120.0 . . ? C6 C7 C2 119.64(16) . . ? C6 C7 H7 120.2 . . ? C2 C7 H7 120.2 . . ? C9 N4 C10 123.77(13) . . ? C9 N4 H4A 118.1 . . ? C10 N4 H4A 118.1 . . ? C18 C19 C20 120.82(15) . . ? C18 C19 H19 119.6 . . ? C20 C19 H19 119.6 . . ? C24 N2 C25 123.46(13) . . ? C24 N2 H2 118.3 . . ? C25 N2 H2 118.3 . . ? C4 C5 C6 119.79(15) . . ? C4 C5 C8 123.16(14) . . ? C6 C5 C8 116.91(15) . . ? C8 N3 C9 126.89(14) . . ? C8 N3 H3A 116.6 . . ? C9 N3 H3A 116.6 . . ? C3 C2 C7 120.54(15) . . ? C3 C2 C1 120.80(16) . . ? C7 C2 C1 118.66(15) . . ? C7 C6 C5 120.11(16) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? O2 C8 N3 122.71(15) . . ? O2 C8 C5 120.09(14) . . ? N3 C8 C5 117.18(14) . . ? F5 C1 F4 106.54(15) . . ? F5 C1 F6 106.77(14) . . ? F4 C1 F6 105.83(15) . . ? F5 C1 C2 112.85(15) . . ? F4 C1 C2 112.13(14) . . ? F6 C1 C2 112.24(15) . . ? F1 C16 F3 106.82(15) . . ? F1 C16 F2 105.68(14) . . ? F3 C16 F2 106.19(14) . . ? F1 C16 C17 112.72(14) . . ? F3 C16 C17 112.59(14) . . ? F2 C16 C17 112.33(14) . . ? C10 C11 C12 114.30(13) . . ? C10 C11 H11A 108.7 . . ? C12 C11 H11A 108.7 . . ? C10 C11 H11B 108.7 . . ? C12 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C18 C17 C22 120.29(15) . . ? C18 C17 C16 120.19(14) . . ? C22 C17 C16 119.51(15) . . ? C21 C20 C19 119.52(15) . . ? C21 C20 C23 123.49(14) . . ? C19 C20 C23 116.84(14) . . ? C14 C13 C12 114.21(14) . . ? C14 C13 H13A 108.7 . . ? C12 C13 H13A 108.7 . . ? C14 C13 H13B 108.7 . . ? C12 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? C25 C26 C27 114.55(13) . . ? C25 C26 H26A 108.6 . . ? C27 C26 H26A 108.6 . . ? C25 C26 H26B 108.6 . . ? C27 C26 H26B 108.6 . . ? H26A C26 H26B 107.6 . . ? N2 C24 N1 117.18(13) . . ? N2 C24 S1 123.03(12) . . ? N1 C24 S1 119.79(12) . . ? C26 C27 C28 112.90(13) . . ? C26 C27 H27A 109.0 . . ? C28 C27 H27A 109.0 . . ? C26 C27 H27B 109.0 . . ? C28 C27 H27B 109.0 . . ? H27A C27 H27B 107.8 . . ? C29 C28 C27 114.28(14) . . ? C29 C28 H28A 108.7 . . ? C27 C28 H28A 108.7 . . ? C29 C28 H28B 108.7 . . ? C27 C28 H28B 108.7 . . ? H28A C28 H28B 107.6 . . ? C13 C12 C11 113.15(13) . . ? C13 C12 H12A 108.9 . . ? C11 C12 H12A 108.9 . . ? C13 C12 H12B 108.9 . . ? C11 C12 H12B 108.9 . . ? H12A C12 H12B 107.8 . . ? O1 C23 N1 122.62(15) . . ? O1 C23 C20 119.87(14) . . ? N1 C23 C20 117.51(14) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C28 C29 C30 112.67(14) . . ? C28 C29 H29A 109.1 . . ? C30 C29 H29A 109.1 . . ? C28 C29 H29B 109.1 . . ? C30 C29 H29B 109.1 . . ? H29A C29 H29B 107.8 . . ? N2 C25 C26 110.35(13) . . ? N2 C25 H25A 109.6 . . ? C26 C25 H25A 109.6 . . ? N2 C25 H25B 109.6 . . ? C26 C25 H25B 109.6 . . ? H25A C25 H25B 108.1 . . ? N4 C9 N3 116.90(14) . . ? N4 C9 S2 123.92(12) . . ? N3 C9 S2 119.18(12) . . ? N4 C10 C11 110.34(13) . . ? N4 C10 H10A 109.6 . . ? C11 C10 H10A 109.6 . . ? N4 C10 H10B 109.6 . . ? C11 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? C13 C14 C15 113.04(15) . . ? C13 C14 H14A 109.0 . . ? C15 C14 H14A 109.0 . . ? C13 C14 H14B 109.0 . . ? C15 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 S1 0.88 2.61 3.4905(14) 176.4 2_566 N4 H4A O2 0.88 1.92 2.6194(17) 134.8 . N2 H2 O1 0.88 1.93 2.6204(17) 134.4 . _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.324 _refine_diff_density_min -0.404 _refine_diff_density_rms 0.058 _database_code_depnum_ccdc_archive 'CCDC 941595' ####################################################################### # # 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_shelxa _audit_creation_method SHELXL-97 _chemical_compound_source 'Cally-Jo Elizabeth Haynes' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H22 N2 O2 S' _chemical_formula_sum 'C15 H22 N2 O2 S' _chemical_formula_weight 294.41 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' S S 0.1246 0.1234 '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/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 18.395(8) _cell_length_b 8.682(4) _cell_length_c 9.855(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.783(6) _cell_angle_gamma 90.00 _cell_volume 1555.4(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3306 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 31.5 _exptl_crystal_description chip _exptl_crystal_colour colourless _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.212 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9874 _exptl_absorpt_correction_T_max 0.9979 _exptl_absorpt_process_details ; Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.475 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_source 'Rotating Anode' _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_collimation 'Confocal mirrors, HF Varimax ' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 (Right)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen MicroMesh' _diffrn_reflns_number 9058 _diffrn_reflns_av_R_equivalents 0.1258 _diffrn_reflns_av_sigmaI/netI 0.1076 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 25.34 _reflns_number_total 2842 _reflns_number_gt 2267 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'WINGX (Farrugia, 1998)' _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. The Rint value > than 0.10 is due to the size of the crystal used. ; _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^)+(0.0539P)^2^+1.0507P] 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 2842 _refine_ls_number_parameters 196 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0810 _refine_ls_R_factor_gt 0.0614 _refine_ls_wR_factor_ref 0.1513 _refine_ls_wR_factor_gt 0.1388 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.13184(15) 0.1241(3) 0.4732(3) 0.0191(6) Uani 1 1 d . . . C2 C -0.10245(16) 0.0374(3) 0.5874(3) 0.0208(6) Uani 1 1 d . . . H2 H -0.1306 -0.0431 0.6191 0.025 Uiso 1 1 calc R . . C3 C -0.03267(16) 0.0680(3) 0.6544(3) 0.0189(6) Uani 1 1 d . . . H3 H -0.0130 0.0083 0.7322 0.023 Uiso 1 1 calc R . . C4 C 0.00959(15) 0.1861(3) 0.6092(3) 0.0171(6) Uani 1 1 d . . . C5 C -0.02127(15) 0.2745(3) 0.4965(3) 0.0203(6) Uani 1 1 d . . . H5 H 0.0063 0.3565 0.4658 0.024 Uiso 1 1 calc R . . C6 C -0.09175(15) 0.2443(3) 0.4286(3) 0.0194(6) Uani 1 1 d . . . H6 H -0.1123 0.3054 0.3523 0.023 Uiso 1 1 calc R . . C7 C 0.08502(15) 0.2091(3) 0.6828(3) 0.0177(6) Uani 1 1 d . . . C8 C 0.20482(15) 0.3383(3) 0.6625(3) 0.0176(6) Uani 1 1 d . . . C9 C -0.22660(16) 0.1483(4) 0.2792(3) 0.0268(7) Uani 1 1 d . . . H9A H -0.2758 0.1085 0.2448 0.040 Uiso 1 1 calc R . . H9B H -0.1931 0.1226 0.2142 0.040 Uiso 1 1 calc R . . H9C H -0.2289 0.2605 0.2892 0.040 Uiso 1 1 calc R . . C10 C 0.30939(15) 0.3298(3) 0.8496(3) 0.0203(6) Uani 1 1 d . . . H10A H 0.3115 0.3287 0.9506 0.024 Uiso 1 1 calc R A 1 H10B H 0.3199 0.4362 0.8219 0.024 Uiso 1 1 calc R A 1 C11A C 0.36811(16) 0.2226(3) 0.8108(3) 0.0238(7) Uani 0.680(5) 1 d PD B 1 H11A H 0.3617 0.2132 0.7096 0.029 Uiso 0.680(5) 1 calc PR B 1 H11B H 0.3613 0.1190 0.8490 0.029 Uiso 0.680(5) 1 calc PR B 1 C12A C 0.4460(3) 0.2777(9) 0.8628(7) 0.0229(16) Uani 0.680(5) 1 d PD B 1 H12A H 0.4529 0.2833 0.9642 0.028 Uiso 0.680(5) 1 calc PR B 1 H12B H 0.4520 0.3831 0.8277 0.028 Uiso 0.680(5) 1 calc PR B 1 C13A C 0.5058(3) 0.1741(10) 0.8196(6) 0.0243(16) Uani 0.680(5) 1 d PD B 1 H13A H 0.5044 0.0735 0.8664 0.029 Uiso 0.680(5) 1 calc PR B 1 H13B H 0.4942 0.1552 0.7196 0.029 Uiso 0.680(5) 1 calc PR B 1 C14A C 0.5838(2) 0.2388(6) 0.8514(5) 0.0332(11) Uani 0.680(5) 1 d PD B 1 H14A H 0.6174 0.1685 0.8119 0.040 Uiso 0.680(5) 1 calc PR B 1 H14B H 0.5850 0.3394 0.8046 0.040 Uiso 0.680(5) 1 calc PR B 1 C15A C 0.6128(3) 0.2608(7) 1.0020(6) 0.0409(14) Uani 0.680(5) 1 d PD B 1 H15A H 0.5842 0.3411 1.0397 0.061 Uiso 0.680(5) 1 calc PR B 1 H15B H 0.6646 0.2918 1.0128 0.061 Uiso 0.680(5) 1 calc PR B 1 H15C H 0.6084 0.1639 1.0511 0.061 Uiso 0.680(5) 1 calc PR B 1 C11B C 0.36811(16) 0.2226(3) 0.8108(3) 0.0238(7) Uani 0.320(5) 1 d PD B 2 H11C H 0.3540 0.1145 0.8251 0.029 Uiso 0.320(5) 1 calc PR B 2 H11D H 0.3719 0.2360 0.7124 0.029 Uiso 0.320(5) 1 calc PR B 2 C12B C 0.4417(7) 0.256(2) 0.8962(18) 0.0229(16) Uani 0.320(5) 1 d PD B 2 H12C H 0.4382 0.2397 0.9945 0.028 Uiso 0.320(5) 1 calc PR B 2 H12D H 0.4552 0.3644 0.8837 0.028 Uiso 0.320(5) 1 calc PR B 2 C13B C 0.5011(7) 0.151(2) 0.8554(16) 0.0243(16) Uani 0.320(5) 1 d PD B 2 H13C H 0.4854 0.0429 0.8636 0.029 Uiso 0.320(5) 1 calc PR B 2 H13D H 0.5044 0.1700 0.7575 0.029 Uiso 0.320(5) 1 calc PR B 2 C14B C 0.5767(5) 0.1696(12) 0.9372(11) 0.0332(11) Uani 0.320(5) 1 d PD B 2 H14C H 0.5747 0.1376 1.0330 0.040 Uiso 0.320(5) 1 calc PR B 2 H14D H 0.6105 0.0982 0.8995 0.040 Uiso 0.320(5) 1 calc PR B 2 C15B C 0.6088(7) 0.3285(14) 0.9398(14) 0.0409(14) Uani 0.320(5) 1 d PD B 2 H15D H 0.6049 0.3679 0.8458 0.061 Uiso 0.320(5) 1 calc PR B 2 H15E H 0.6606 0.3250 0.9815 0.061 Uiso 0.320(5) 1 calc PR B 2 H15F H 0.5817 0.3966 0.9937 0.061 Uiso 0.320(5) 1 calc PR B 2 N1 N 0.13237(12) 0.2922(3) 0.6153(2) 0.0175(5) Uani 1 1 d . . . H1 H 0.1147 0.3202 0.5309 0.021 Uiso 1 1 calc R . . N2 N 0.23539(12) 0.2866(3) 0.7849(2) 0.0187(5) Uani 1 1 d . B . H2A H 0.2098 0.2234 0.8292 0.022 Uiso 1 1 calc R . . O1 O 0.10497(11) 0.1553(2) 0.79881(19) 0.0207(5) Uani 1 1 d . . . O2 O -0.20006(11) 0.0797(2) 0.4108(2) 0.0253(5) Uani 1 1 d . . . S1 S 0.24572(4) 0.45572(8) 0.56227(7) 0.0212(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 0.0152(14) 0.0224(15) 0.0193(14) -0.0052(12) 0.0012(12) 0.0006(11) C2 0.0223(15) 0.0221(15) 0.0189(14) -0.0034(12) 0.0060(13) -0.0054(12) C3 0.0237(15) 0.0192(15) 0.0137(13) -0.0012(11) 0.0022(12) -0.0011(12) C4 0.0180(14) 0.0180(15) 0.0153(14) -0.0048(11) 0.0023(12) 0.0015(11) C5 0.0192(14) 0.0204(15) 0.0216(15) 0.0014(12) 0.0041(13) 0.0008(12) C6 0.0200(14) 0.0209(15) 0.0172(14) 0.0025(11) 0.0018(12) 0.0016(12) C7 0.0193(14) 0.0177(14) 0.0164(14) -0.0034(11) 0.0039(12) 0.0005(12) C8 0.0186(14) 0.0159(14) 0.0184(14) -0.0033(11) 0.0034(12) 0.0004(11) C9 0.0240(16) 0.0277(17) 0.0255(16) -0.0015(13) -0.0068(14) -0.0023(13) C10 0.0176(14) 0.0240(15) 0.0186(14) 0.0001(12) -0.0002(12) -0.0023(12) C11A 0.0200(15) 0.0281(16) 0.0229(15) -0.0014(13) 0.0022(13) 0.0011(13) C12A 0.0208(18) 0.031(3) 0.017(4) 0.004(3) 0.001(2) 0.0003(17) C13A 0.0218(19) 0.033(3) 0.018(4) 0.006(3) 0.004(2) 0.0044(17) C14A 0.022(2) 0.042(3) 0.035(3) 0.005(2) 0.003(2) 0.009(2) C15A 0.023(2) 0.051(4) 0.045(4) -0.012(3) -0.005(3) 0.000(3) C11B 0.0200(15) 0.0281(16) 0.0229(15) -0.0014(13) 0.0022(13) 0.0011(13) C12B 0.0208(18) 0.031(3) 0.017(4) 0.004(3) 0.001(2) 0.0003(17) C13B 0.0218(19) 0.033(3) 0.018(4) 0.006(3) 0.004(2) 0.0044(17) C14B 0.022(2) 0.042(3) 0.035(3) 0.005(2) 0.003(2) 0.009(2) C15B 0.023(2) 0.051(4) 0.045(4) -0.012(3) -0.005(3) 0.000(3) N1 0.0157(12) 0.0220(12) 0.0144(11) 0.0000(9) 0.0010(10) -0.0014(10) N2 0.0174(12) 0.0233(13) 0.0156(12) -0.0023(10) 0.0032(10) -0.0037(10) O1 0.0203(10) 0.0258(11) 0.0154(10) 0.0008(8) 0.0005(9) -0.0009(8) O2 0.0189(11) 0.0296(12) 0.0250(11) 0.0009(9) -0.0044(9) -0.0050(9) S1 0.0209(4) 0.0247(4) 0.0182(4) 0.0004(3) 0.0033(3) -0.0037(3) _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 O2 1.366(3) . ? C1 C6 1.387(4) . ? C1 C2 1.393(4) . ? C2 C3 1.377(4) . ? C2 H2 0.9500 . ? C3 C4 1.400(4) . ? C3 H3 0.9500 . ? C4 C5 1.397(4) . ? C4 C7 1.478(4) . ? C5 C6 1.390(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O1 1.237(3) . ? C7 N1 1.378(4) . ? C8 N2 1.329(3) . ? C8 N1 1.401(3) . ? C8 S1 1.676(3) . ? C9 O2 1.443(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 N2 1.461(3) . ? C10 C11A 1.518(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11A C12A 1.523(7) . ? C11A H11A 0.9900 . ? C11A H11B 0.9900 . ? C12A C13A 1.531(7) . ? C12A H12A 0.9900 . ? C12A H12B 0.9900 . ? C13A C14A 1.528(7) . ? C13A H13A 0.9900 . ? C13A H13B 0.9900 . ? C14A C15A 1.510(7) . ? C14A H14A 0.9900 . ? C14A H14B 0.9900 . ? C15A H15A 0.9800 . ? C15A H15B 0.9800 . ? C15A H15C 0.9800 . ? C12B C13B 1.520(14) . ? C12B H12C 0.9900 . ? C12B H12D 0.9900 . ? C13B C14B 1.507(13) . ? C13B H13C 0.9900 . ? C13B H13D 0.9900 . ? C14B C15B 1.499(13) . ? C14B H14C 0.9900 . ? C14B H14D 0.9900 . ? C15B H15D 0.9800 . ? C15B H15E 0.9800 . ? C15B H15F 0.9800 . ? N1 H1 0.8800 . ? N2 H2A 0.8800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 C6 124.5(2) . . ? O2 C1 C2 115.3(2) . . ? C6 C1 C2 120.2(2) . . ? C3 C2 C1 120.1(3) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 120.7(3) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C5 C4 C3 118.5(2) . . ? C5 C4 C7 123.6(3) . . ? C3 C4 C7 117.9(2) . . ? C6 C5 C4 121.0(3) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C1 C6 C5 119.4(3) . . ? C1 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? O1 C7 N1 121.6(2) . . ? O1 C7 C4 121.8(3) . . ? N1 C7 C4 116.7(2) . . ? N2 C8 N1 117.0(2) . . ? N2 C8 S1 125.1(2) . . ? N1 C8 S1 117.90(19) . . ? O2 C9 H9A 109.5 . . ? O2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 C11A 112.6(2) . . ? N2 C10 H10A 109.1 . . ? C11A C10 H10A 109.1 . . ? N2 C10 H10B 109.1 . . ? C11A C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? C10 C11A C12A 113.1(4) . . ? C10 C11A H11A 109.0 . . ? C12A C11A H11A 109.0 . . ? C10 C11A H11B 109.0 . . ? C12A C11A H11B 109.0 . . ? H11A C11A H11B 107.8 . . ? C11A C12A C13A 113.6(5) . . ? C11A C12A H12A 108.8 . . ? C13A C12A H12A 108.8 . . ? C11A C12A H12B 108.8 . . ? C13A C12A H12B 108.8 . . ? H12A C12A H12B 107.7 . . ? C14A C13A C12A 114.8(6) . . ? C14A C13A H13A 108.6 . . ? C12A C13A H13A 108.6 . . ? C14A C13A H13B 108.6 . . ? C12A C13A H13B 108.6 . . ? H13A C13A H13B 107.6 . . ? C15A C14A C13A 115.3(5) . . ? C15A C14A H14A 108.4 . . ? C13A C14A H14A 108.4 . . ? C15A C14A H14B 108.4 . . ? C13A C14A H14B 108.4 . . ? H14A C14A H14B 107.5 . . ? C13B C12B H12C 109.4 . . ? C13B C12B H12D 109.4 . . ? H12C C12B H12D 108.0 . . ? C14B C13B C12B 115.9(12) . . ? C14B C13B H13C 108.3 . . ? C12B C13B H13C 108.3 . . ? C14B C13B H13D 108.3 . . ? C12B C13B H13D 108.3 . . ? H13C C13B H13D 107.4 . . ? C15B C14B C13B 115.8(10) . . ? C15B C14B H14C 108.3 . . ? C13B C14B H14C 108.3 . . ? C15B C14B H14D 108.3 . . ? C13B C14B H14D 108.3 . . ? H14C C14B H14D 107.4 . . ? C14B C15B H15D 109.5 . . ? C14B C15B H15E 109.5 . . ? H15D C15B H15E 109.5 . . ? C14B C15B H15F 109.5 . . ? H15D C15B H15F 109.5 . . ? H15E C15B H15F 109.5 . . ? C7 N1 C8 128.9(2) . . ? C7 N1 H1 115.5 . . ? C8 N1 H1 115.5 . . ? C8 N2 C10 123.1(2) . . ? C8 N2 H2A 118.4 . . ? C10 N2 H2A 118.4 . . ? C1 O2 C9 116.7(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.88 2.28 3.116(3) 159.4 4_565 N2 H2A O1 0.88 2.00 2.678(3) 133.4 . N2 H2A S1 0.88 2.77 3.431(3) 133.1 4_566 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.340 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.067 _iucr_refine_instructions_details ; TITL shelxa in P2(1)/c CELL 0.71073 18.3951 8.6816 9.8549 90.000 98.783 90.000 ZERR 4.00 0.0083 0.0039 0.0046 0.000 0.006 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O S UNIT 60 88 8 8 4 MERG 2 SHEL 7 0.83 EADP C11A C11B EADP C12A C12B EADP C13A C13B EADP C14A C14B EADP C15A C15B EXYZ C11A C11B HTAB N1 O1_$1 HTAB N2 O1 HTAB N2 S1_$2 EQIV $1 x, -y+1/2, z-1/2 EQIV $2 x, -y+1/2, z+1/2 FMAP 2 PLAN 20 SIZE 0.01 0.04 0.06 ACTA 55.00 BOND $H L.S. 20 TEMP -173.00 WGHT 0.053900 1.050700 FVAR 0.52617 0.67966 C1 1 -0.131835 0.124146 0.473154 11.00000 0.01522 0.02241 = 0.01931 -0.00520 0.00118 0.00063 C2 1 -0.102450 0.037364 0.587388 11.00000 0.02226 0.02210 = 0.01890 -0.00338 0.00601 -0.00538 AFIX 43 H2 2 -0.130602 -0.043056 0.619071 11.00000 -1.20000 AFIX 0 C3 1 -0.032671 0.067987 0.654422 11.00000 0.02370 0.01922 = 0.01370 -0.00123 0.00221 -0.00108 AFIX 43 H3 2 -0.012981 0.008320 0.732218 11.00000 -1.20000 AFIX 0 C4 1 0.009589 0.186119 0.609180 11.00000 0.01802 0.01799 = 0.01534 -0.00482 0.00231 0.00146 C5 1 -0.021272 0.274473 0.496514 11.00000 0.01922 0.02035 = 0.02156 0.00141 0.00409 0.00077 AFIX 43 H5 2 0.006324 0.356453 0.465838 11.00000 -1.20000 AFIX 0 C6 1 -0.091754 0.244288 0.428577 11.00000 0.01999 0.02086 = 0.01715 0.00254 0.00180 0.00162 AFIX 43 H6 2 -0.112277 0.305411 0.352301 11.00000 -1.20000 AFIX 0 C7 1 0.085025 0.209091 0.682821 11.00000 0.01933 0.01767 = 0.01638 -0.00336 0.00386 0.00052 C8 1 0.204824 0.338296 0.662489 11.00000 0.01861 0.01587 = 0.01835 -0.00326 0.00338 0.00037 C9 1 -0.226604 0.148337 0.279221 11.00000 0.02404 0.02767 = 0.02549 -0.00152 -0.00681 -0.00226 AFIX 33 H9A 2 -0.275819 0.108506 0.244812 11.00000 -1.50000 H9B 2 -0.193105 0.122635 0.214219 11.00000 -1.50000 H9C 2 -0.228917 0.260462 0.289241 11.00000 -1.50000 AFIX 0 C10 1 0.309387 0.329799 0.849577 11.00000 0.01759 0.02397 = 0.01856 0.00006 -0.00020 -0.00232 AFIX 23 H10A 2 0.311497 0.328695 0.950556 11.00000 -1.20000 H10B 2 0.319856 0.436171 0.821942 11.00000 -1.20000 AFIX 0 PART 1 SAME C11B > C15B C11A 1 0.368106 0.222630 0.810827 21.00000 0.02004 0.02811 = 0.02287 -0.00139 0.00224 0.00105 AFIX 23 H11A 2 0.361739 0.213198 0.709590 21.00000 -1.20000 H11B 2 0.361289 0.119046 0.848969 21.00000 -1.20000 AFIX 0 C12A 1 0.446004 0.277749 0.862752 21.00000 0.02079 0.03084 = 0.01662 0.00411 0.00103 0.00028 AFIX 23 H12A 2 0.452866 0.283253 0.964247 21.00000 -1.20000 H12B 2 0.452031 0.383126 0.827720 21.00000 -1.20000 AFIX 0 C13A 1 0.505807 0.174088 0.819598 21.00000 0.02184 0.03336 = 0.01792 0.00561 0.00378 0.00445 AFIX 23 H13A 2 0.504439 0.073488 0.866444 21.00000 -1.20000 H13B 2 0.494173 0.155241 0.719558 21.00000 -1.20000 AFIX 0 C14A 1 0.583776 0.238771 0.851405 21.00000 0.02207 0.04238 = 0.03472 0.00482 0.00334 0.00943 AFIX 23 H14A 2 0.617408 0.168507 0.811887 21.00000 -1.20000 H14B 2 0.585003 0.339416 0.804579 21.00000 -1.20000 AFIX 0 C15A 1 0.612780 0.260815 1.001980 21.00000 0.02348 0.05068 = 0.04532 -0.01187 -0.00474 -0.00006 AFIX 137 H15A 2 0.584172 0.341062 1.039722 21.00000 -1.50000 H15B 2 0.664578 0.291763 1.012799 21.00000 -1.50000 H15C 2 0.608409 0.163923 1.051115 21.00000 -1.50000 AFIX 0 PART 2 SAME C11A > C15A C11B 1 0.368106 0.222630 0.810827 -21.00000 0.02004 0.02811 = 0.02287 -0.00139 0.00224 0.00105 AFIX 23 H11C 2 0.353975 0.114477 0.825091 -21.00000 -1.20000 H11D 2 0.371862 0.236048 0.712379 -21.00000 -1.20000 AFIX 0 C12B 1 0.441706 0.255530 0.896177 -21.00000 0.02079 0.03084 = 0.01662 0.00411 0.00103 0.00028 AFIX 23 H12C 2 0.438213 0.239678 0.994455 -21.00000 -1.20000 H12D 2 0.455211 0.364433 0.883684 -21.00000 -1.20000 AFIX 0 C13B 1 0.501068 0.151152 0.855388 -21.00000 0.02184 0.03336 = 0.01792 0.00561 0.00378 0.00445 AFIX 23 H13C 2 0.485371 0.042913 0.863617 -21.00000 -1.20000 H13D 2 0.504449 0.169983 0.757470 -21.00000 -1.20000 AFIX 0 C14B 1 0.576715 0.169574 0.937240 -21.00000 0.02207 0.04238 = 0.03472 0.00482 0.00334 0.00943 AFIX 23 H14C 2 0.574689 0.137550 1.033005 -21.00000 -1.20000 H14D 2 0.610533 0.098164 0.899522 -21.00000 -1.20000 AFIX 0 C15B 1 0.608783 0.328528 0.939789 -21.00000 0.02348 0.05068 = 0.04532 -0.01187 -0.00474 -0.00006 AFIX 137 H15D 2 0.604925 0.367861 0.845751 -21.00000 -1.50000 H15E 2 0.660642 0.324979 0.981544 -21.00000 -1.50000 H15F 2 0.581743 0.396629 0.993738 -21.00000 -1.50000 AFIX 0 PART 0 N1 3 0.132369 0.292223 0.615280 11.00000 0.01572 0.02204 = 0.01444 0.00000 0.00104 -0.00136 AFIX 43 H1 2 0.114656 0.320228 0.530875 11.00000 -1.20000 AFIX 0 N2 3 0.235386 0.286629 0.784930 11.00000 0.01739 0.02329 = 0.01560 -0.00232 0.00320 -0.00373 AFIX 43 H2A 2 0.209843 0.223425 0.829160 11.00000 -1.20000 AFIX 0 O1 4 0.104970 0.155304 0.798810 11.00000 0.02029 0.02578 = 0.01537 0.00083 0.00054 -0.00086 O2 4 -0.200064 0.079747 0.410814 11.00000 0.01894 0.02955 = 0.02499 0.00095 -0.00444 -0.00496 S1 5 0.245718 0.455722 0.562275 11.00000 0.02094 0.02469 = 0.01818 0.00045 0.00331 -0.00368 HKLF 4 REM shelxa in P2(1)/c REM R1 = 0.0614 for 2267 Fo > 4sig(Fo) and 0.0810 for all 2842 data REM 196 parameters refined using 7 restraints END WGHT 0.0475 0.1382 REM Highest difference peak 0.340, deepest hole -0.271, 1-sigma level 0.067 Q1 1 0.3172 0.4793 0.5380 11.00000 0.05 0.34 Q2 1 0.0415 0.1449 0.8393 11.00000 0.05 0.33 Q3 1 0.1936 0.4607 0.6129 11.00000 0.05 0.32 Q4 1 -0.0304 0.1724 0.6616 11.00000 0.05 0.31 Q5 1 0.2581 0.3409 0.5858 11.00000 0.05 0.26 Q6 1 -0.1160 0.0845 0.5219 11.00000 0.05 0.25 Q7 1 0.2478 0.5773 0.5795 11.00000 0.05 0.24 Q8 1 0.1594 0.0615 0.8985 11.00000 0.05 0.24 Q9 1 0.6388 -0.0512 0.9404 11.00000 0.05 0.24 Q10 1 0.3028 0.4470 0.8431 11.00000 0.05 0.24 Q11 1 0.6268 0.1034 1.0096 11.00000 0.05 0.23 Q12 1 0.2481 0.4685 0.6964 11.00000 0.05 0.23 Q13 1 0.5379 0.2259 0.8880 11.00000 0.05 0.22 Q14 1 -0.0949 0.1405 0.4064 11.00000 0.05 0.22 Q15 1 -0.0168 0.2555 0.5767 11.00000 0.05 0.21 Q16 1 -0.2071 -0.0326 0.1755 11.00000 0.05 0.21 Q17 1 -0.1261 0.1481 0.5760 11.00000 0.05 0.21 Q18 1 0.6921 0.1621 1.0378 11.00000 0.05 0.21 Q19 1 -0.2645 0.0889 0.4301 11.00000 0.05 0.21 Q20 1 -0.2598 0.0411 0.2549 11.00000 0.05 0.21 ; _database_code_depnum_ccdc_archive 'CCDC 941596' ####################################################################### # # 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_2012sot0005 #O1O-H2PO4 _audit_creation_method SHELXL-97 _chemical_compound_source 'Cally-Jo Elizabeth Haynes' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H20 N2 O2' _chemical_formula_sum 'C14 H20 N2 O2' _chemical_formula_weight 248.32 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.166(3) _cell_length_b 34.07(2) _cell_length_c 7.566(5) _cell_angle_alpha 90.00 _cell_angle_beta 101.193(10) _cell_angle_gamma 90.00 _cell_volume 1306.3(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3816 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 31.3 _exptl_crystal_description Lath _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9832 _exptl_absorpt_correction_T_max 0.9983 _exptl_absorpt_process_details ; Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.475 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_source 'Rotating Anode' _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_collimation 'Confocal mirrors, HF Varimax ' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 (Right)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen MicroMesh' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4606 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_sigmaI/netI 0.0659 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 40 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2078 _reflns_number_gt 1589 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Images generated using CrystalMaker: a crystal and molecular structures program for Mac and Windows. CrystalMaker Software Ltd, Oxford, England (www.crystalmaker.com) ; _computing_publication_material 'WINGX (Farrugia, 1998)' _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. The data were collected using an orthorhombic strategy, and the structure is actually monoclinic - thus the data are not complete. ; _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^)+(0.0463P)^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 2078 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0708 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1083 _refine_ls_wR_factor_gt 0.0988 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.004 _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 O1 O 0.7762(2) 0.21454(4) 0.4437(2) 0.0203(4) Uani 1 1 d . . . O2 O 1.4293(2) 0.14138(4) 0.5316(2) 0.0245(4) Uani 1 1 d . . . N1 N 1.2159(3) 0.19982(5) 0.4918(3) 0.0181(4) Uani 1 1 d . . . H1 H 1.3726 0.2106 0.5007 0.022 Uiso 1 1 calc R . . N2 N 0.9817(3) 0.14053(4) 0.4854(3) 0.0181(4) Uani 1 1 d . . . H2 H 0.8353 0.1540 0.4516 0.022 Uiso 1 1 calc R . . C1 C 0.8892(4) 0.29465(5) 0.3916(3) 0.0186(5) Uani 1 1 d . . . H1A H 0.7238 0.2853 0.3284 0.022 Uiso 1 1 calc R . . C2 C 0.9389(4) 0.33457(6) 0.3978(3) 0.0222(5) Uani 1 1 d . . . H2A H 0.8104 0.3524 0.3373 0.027 Uiso 1 1 calc R . . C3 C 1.1791(4) 0.34828(6) 0.4935(3) 0.0224(5) Uani 1 1 d . . . H3 H 1.2145 0.3757 0.4989 0.027 Uiso 1 1 calc R . . C4 C 1.3663(4) 0.32238(6) 0.5805(3) 0.0222(6) Uani 1 1 d . . . H4 H 1.5287 0.3320 0.6472 0.027 Uiso 1 1 calc R . . C5 C 1.3190(4) 0.28232(6) 0.5715(3) 0.0194(5) Uani 1 1 d . . . H5 H 1.4502 0.2646 0.6296 0.023 Uiso 1 1 calc R . . C6 C 1.0775(4) 0.26797(5) 0.4764(3) 0.0169(5) Uani 1 1 d . . . C7 C 1.0089(4) 0.22544(6) 0.4683(3) 0.0169(5) Uani 1 1 d . . . C8 C 1.2147(4) 0.15834(6) 0.5040(3) 0.0181(5) Uani 1 1 d . . . C9 C 0.9693(4) 0.09851(5) 0.5213(3) 0.0198(5) Uani 1 1 d . . . H9A H 0.7982 0.0926 0.5559 0.024 Uiso 1 1 calc R . . H9B H 1.1109 0.0918 0.6250 0.024 Uiso 1 1 calc R . . C10 C 0.9983(4) 0.07276(6) 0.3623(3) 0.0215(6) Uani 1 1 d . . . H10A H 1.0054 0.0450 0.4011 0.026 Uiso 1 1 calc R . . H10B H 1.1683 0.0790 0.3267 0.026 Uiso 1 1 calc R . . C11 C 0.7767(4) 0.07743(6) 0.1979(3) 0.0227(6) Uani 1 1 d . . . H11A H 0.6058 0.0724 0.2344 0.027 Uiso 1 1 calc R . . H11B H 0.7753 0.1049 0.1548 0.027 Uiso 1 1 calc R . . C12 C 0.8020(4) 0.05004(6) 0.0435(3) 0.0230(6) Uani 1 1 d . . . H12A H 0.8087 0.0227 0.0880 0.028 Uiso 1 1 calc R . . H12B H 0.9714 0.0555 0.0056 0.028 Uiso 1 1 calc R . . C13 C 0.5795(4) 0.05339(6) -0.1208(3) 0.0250(6) Uani 1 1 d . . . H13A H 0.4090 0.0492 -0.0824 0.030 Uiso 1 1 calc R . . H13B H 0.5786 0.0803 -0.1698 0.030 Uiso 1 1 calc R . . C14 C 0.6021(4) 0.02426(6) -0.2697(4) 0.0291(6) Uani 1 1 d . . . H14A H 0.7695 0.0284 -0.3096 0.044 Uiso 1 1 calc R . . H14B H 0.4551 0.0282 -0.3715 0.044 Uiso 1 1 calc R . . H14C H 0.5961 -0.0026 -0.2238 0.044 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0134(7) 0.0228(8) 0.0247(12) 0.0006(6) 0.0036(7) -0.0014(6) O2 0.0153(7) 0.0213(8) 0.0376(13) 0.0012(7) 0.0067(7) 0.0032(6) N1 0.0119(8) 0.0178(9) 0.0254(14) 0.0000(7) 0.0054(8) -0.0006(7) N2 0.0129(8) 0.0176(9) 0.0237(14) 0.0016(7) 0.0033(8) 0.0021(7) C1 0.0159(10) 0.0234(12) 0.0173(16) -0.0008(9) 0.0051(10) -0.0005(9) C2 0.0236(11) 0.0220(12) 0.0223(17) 0.0041(9) 0.0080(10) 0.0052(9) C3 0.0269(11) 0.0177(11) 0.0256(17) -0.0013(9) 0.0128(11) -0.0008(9) C4 0.0180(10) 0.0251(13) 0.0249(18) -0.0027(9) 0.0077(10) -0.0043(9) C5 0.0165(10) 0.0216(12) 0.0206(17) -0.0012(9) 0.0047(10) 0.0021(9) C6 0.0168(10) 0.0179(11) 0.0179(15) 0.0001(9) 0.0078(10) 0.0010(9) C7 0.0179(10) 0.0230(12) 0.0103(15) 0.0000(8) 0.0039(9) 0.0014(9) C8 0.0173(10) 0.0219(12) 0.0161(16) -0.0025(9) 0.0054(10) 0.0021(9) C9 0.0175(10) 0.0183(11) 0.0242(16) 0.0032(9) 0.0053(10) 0.0000(9) C10 0.0172(10) 0.0177(11) 0.0304(18) -0.0020(9) 0.0068(10) 0.0002(9) C11 0.0192(10) 0.0181(12) 0.0318(19) -0.0002(9) 0.0079(11) 0.0014(9) C12 0.0195(10) 0.0199(12) 0.0310(19) -0.0020(9) 0.0083(11) -0.0009(9) C13 0.0230(11) 0.0230(12) 0.0295(19) -0.0006(10) 0.0063(11) 0.0004(9) C14 0.0338(12) 0.0265(13) 0.0281(19) -0.0009(10) 0.0083(12) 0.0000(10) _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 C7 1.237(2) . ? O2 C8 1.232(2) . ? N1 C7 1.365(2) . ? N1 C8 1.416(3) . ? N2 C8 1.331(2) . ? N2 C9 1.461(2) . ? C1 C2 1.383(3) . ? C1 C6 1.393(3) . ? C2 C3 1.391(3) . ? C3 C4 1.378(3) . ? C4 C5 1.386(3) . ? C5 C6 1.402(3) . ? C6 C7 1.490(3) . ? C9 C10 1.520(3) . ? C10 C11 1.526(3) . ? C11 C12 1.520(3) . ? C12 C13 1.524(3) . ? C13 C14 1.523(3) . ? 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 C7 N1 C8 129.32(16) . . ? C8 N2 C9 119.92(16) . . ? C2 C1 C6 121.16(19) . . ? C1 C2 C3 119.28(19) . . ? C4 C3 C2 120.40(19) . . ? C3 C4 C5 120.4(2) . . ? C4 C5 C6 120.00(19) . . ? C1 C6 C5 118.74(18) . . ? C1 C6 C7 118.46(18) . . ? C5 C6 C7 122.76(18) . . ? O1 C7 N1 122.77(18) . . ? O1 C7 C6 120.95(16) . . ? N1 C7 C6 116.28(16) . . ? O2 C8 N2 124.74(19) . . ? O2 C8 N1 117.66(17) . . ? N2 C8 N1 117.60(17) . . ? N2 C9 C10 113.81(18) . . ? C9 C10 C11 114.29(16) . . ? C12 C11 C10 113.55(16) . . ? C11 C12 C13 114.63(17) . . ? C14 C13 C12 113.61(17) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.88 2.21 3.029(3) 153.8 1_655 N2 H2 O1 0.88 2.08 2.730(2) 129.7 . N2 H2 O2 0.88 2.33 2.941(3) 126.4 1_455 _diffrn_measured_fraction_theta_max 0.905 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.905 _refine_diff_density_max 0.193 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.043 _database_code_depnum_ccdc_archive 'CCDC 941597'