# Electronic Supplementary Material (ESI) for RSC Advances # 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_a1 _database_code_depnum_ccdc_archive 'CCDC 850135' #TrackingRef '7760_web_deposit_cif_file_0_RezaKia_1319402141.2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H10 Cl N2' _chemical_formula_sum 'C13 H10 Cl N2' _chemical_formula_weight 229.68 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' 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_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.115(5) _cell_length_b 12.488(5) _cell_length_c 14.141(5) _cell_angle_alpha 73.839(5) _cell_angle_beta 87.734(5) _cell_angle_gamma 81.732(5) _cell_volume 1194.3(11) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 2534 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 27.45 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476 _exptl_absorpt_coefficient_mu 0.292 _exptl_absorpt_correction_type ;multi-scan' _exptl_absorpt_correction_T_min 0.952 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'MULABS (Blessing, 1995) in PLATON (Spek, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS 2T Image Plate diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean '0.15 mm' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 9389 _diffrn_reflns_av_R_equivalents 0.1026 _diffrn_reflns_av_sigmaI/netI 0.6838 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 29.29 _reflns_number_total 5862 _reflns_number_gt 666 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area 1.52 (Stoe & Cie GmbH, 2009)' _computing_cell_refinement 'X-Area 1.52' _computing_data_reduction 'X-Area 1.52' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL, PLATON (Spek, 2009)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)] 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 5862 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3999 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.0578 _refine_ls_wR_factor_gt 0.0348 _refine_ls_goodness_of_fit_ref 0.475 _refine_ls_restrained_S_all 0.475 _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 Cl1 Cl 0.8243(3) -0.32818(13) 0.75734(13) 0.1083(7) Uani 1 1 d . . . Cl2 Cl 0.3587(3) -0.35515(13) 0.94361(14) 0.1108(7) Uani 1 1 d . . . N3 N 0.0716(8) 0.1289(4) 0.8701(3) 0.0591(14) Uani 1 1 d . . . N1 N 0.5630(9) 0.1456(5) 0.5465(4) 0.0652(16) Uani 1 1 d . . . C21 C -0.0917(10) 0.3018(5) 0.8284(4) 0.0599(17) Uani 1 1 d . . . N4 N 0.1830(7) 0.1969(4) 0.8998(3) 0.0724(16) Uani 1 1 d . . . N2 N 0.6815(7) 0.2045(5) 0.4779(4) 0.0711(16) Uani 1 1 d . . . C6 C 0.6237(12) 0.0299(6) 0.5989(5) 0.0592(19) Uani 1 1 d . . . C8 C 0.4021(11) 0.3132(7) 0.4871(5) 0.0610(18) Uani 1 1 d . . . C19 C 0.1375(11) 0.0126(5) 0.8884(4) 0.0626(19) Uani 1 1 d . . . C3 C 0.7494(13) -0.1865(5) 0.6933(5) 0.072(2) Uani 1 1 d . . . C20 C 0.0821(10) 0.2987(5) 0.8727(4) 0.0637(18) Uani 1 1 d . . . C18 C 0.3174(11) -0.0279(5) 0.9221(4) 0.084(2) Uani 1 1 d . . . H18A H 0.3935 0.0215 0.9343 0.101 Uiso 1 1 calc R . . C16 C 0.2732(12) -0.2116(5) 0.9219(4) 0.073(2) Uani 1 1 d . . . C22 C -0.0945(9) 0.1929(6) 0.8282(4) 0.0621(18) Uani 1 1 d . . . C5 C 0.8091(11) -0.0117(6) 0.5923(5) 0.071(2) Uani 1 1 d . . . H5A H 0.8923 0.0352 0.5560 0.085 Uiso 1 1 calc R . . C9 C 0.3958(11) 0.2108(7) 0.5520(5) 0.0605(19) Uani 1 1 d . . . C13 C 0.6598(8) 0.3934(5) 0.3599(4) 0.103(2) Uani 1 1 d . . . H13A H 0.7956 0.3831 0.3659 0.155 Uiso 1 1 calc R . . H13B H 0.6091 0.4678 0.3632 0.155 Uiso 1 1 calc R . . H13C H 0.6263 0.3838 0.2980 0.155 Uiso 1 1 calc R . . C12 C 0.2233(11) 0.3924(5) 0.4871(5) 0.093(2) Uani 1 1 d . . . H12A H 0.1539 0.4085 0.4260 0.112 Uiso 1 1 calc R . . H12B H 0.2499 0.4625 0.4971 0.112 Uiso 1 1 calc R . . C7 C 0.5784(12) 0.3072(6) 0.4432(5) 0.0656(19) Uani 1 1 d . . . C17 C 0.3906(9) -0.1401(6) 0.9387(4) 0.090(2) Uani 1 1 d . . . H17A H 0.5147 -0.1665 0.9605 0.108 Uiso 1 1 calc R . . C14 C 0.0199(10) -0.0600(6) 0.8719(4) 0.096(3) Uani 1 1 d . . . H14A H -0.1039 -0.0336 0.8495 0.115 Uiso 1 1 calc R . . C25 C -0.2683(8) 0.3750(5) 0.7841(4) 0.080(2) Uani 1 1 d . . . H25A H -0.2394 0.4373 0.7297 0.096 Uiso 1 1 calc R . . H25B H -0.3425 0.4044 0.8327 0.096 Uiso 1 1 calc R . . C1 C 0.4908(10) -0.0336(6) 0.6520(5) 0.087(2) Uani 1 1 d . . . H1A H 0.3639 -0.0045 0.6564 0.105 Uiso 1 1 calc R . . C23 C -0.2667(9) 0.1714(5) 0.7833(4) 0.089(2) Uani 1 1 d . . . H23A H -0.3399 0.1223 0.8313 0.106 Uiso 1 1 calc R . . H23B H -0.2343 0.1398 0.7284 0.106 Uiso 1 1 calc R . . C4 C 0.8752(9) -0.1212(6) 0.6383(5) 0.080(2) Uani 1 1 d . . . H4A H 1.0015 -0.1506 0.6325 0.096 Uiso 1 1 calc R . . C15 C 0.0921(12) -0.1724(6) 0.8897(5) 0.099(3) Uani 1 1 d . . . H15A H 0.0152 -0.2224 0.8795 0.119 Uiso 1 1 calc R . . C2 C 0.5635(11) -0.1455(7) 0.6988(5) 0.082(2) Uani 1 1 d . . . H2A H 0.4814 -0.1933 0.7349 0.098 Uiso 1 1 calc R . . C26 C 0.1540(8) 0.3992(4) 0.8966(4) 0.120(3) Uani 1 1 d . . . H26A H 0.2832 0.3779 0.9190 0.180 Uiso 1 1 calc R . . H26B H 0.0761 0.4205 0.9472 0.180 Uiso 1 1 calc R . . H26C H 0.1474 0.4617 0.8384 0.180 Uiso 1 1 calc R . . C24 C -0.3731(9) 0.2937(6) 0.7486(5) 0.106(2) Uani 1 1 d . . . H24A H -0.3810 0.3173 0.6773 0.127 Uiso 1 1 calc R . . H24B H -0.5014 0.2957 0.7746 0.127 Uiso 1 1 calc R . . C10 C 0.2139(11) 0.2027(5) 0.6097(5) 0.090(2) Uani 1 1 d . . . H10A H 0.2377 0.1795 0.6800 0.109 Uiso 1 1 calc R . . H10B H 0.1406 0.1506 0.5931 0.109 Uiso 1 1 calc R . . C11 C 0.1115(10) 0.3265(7) 0.5750(6) 0.114(2) Uani 1 1 d . . . H11A H -0.0177 0.3272 0.5552 0.137 Uiso 1 1 calc R . . H11B H 0.1071 0.3614 0.6285 0.137 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 Cl1 0.148(2) 0.0701(12) 0.1051(16) -0.0185(11) -0.0140(13) -0.0162(13) Cl2 0.1577(19) 0.0731(12) 0.1044(16) -0.0282(11) -0.0132(13) -0.0142(13) N3 0.060(4) 0.067(4) 0.056(4) -0.020(3) 0.002(3) -0.023(4) N1 0.053(5) 0.079(5) 0.068(5) -0.030(4) 0.003(4) -0.007(4) C21 0.070(6) 0.058(4) 0.054(4) -0.013(3) -0.008(4) -0.017(4) N4 0.065(4) 0.057(3) 0.098(4) -0.020(3) -0.012(3) -0.016(3) N2 0.070(4) 0.067(4) 0.069(4) -0.003(3) -0.001(3) -0.019(4) C6 0.069(6) 0.063(5) 0.050(5) -0.022(4) -0.004(4) -0.007(5) C8 0.047(6) 0.078(5) 0.059(5) -0.022(5) 0.000(4) -0.005(5) C19 0.077(6) 0.064(5) 0.043(4) -0.010(4) -0.012(4) -0.005(5) C3 0.102(7) 0.052(5) 0.068(5) -0.029(4) -0.016(5) 0.003(5) C20 0.066(6) 0.068(5) 0.063(5) -0.021(4) -0.001(4) -0.022(4) C18 0.108(7) 0.052(5) 0.091(5) -0.009(4) -0.029(5) -0.024(5) C16 0.109(7) 0.060(4) 0.047(5) -0.007(4) 0.001(4) -0.016(5) C22 0.061(6) 0.072(5) 0.056(5) -0.017(4) -0.008(4) -0.018(4) C5 0.068(6) 0.061(5) 0.080(5) -0.014(4) 0.008(5) -0.010(5) C9 0.064(7) 0.076(6) 0.050(5) -0.021(5) 0.007(4) -0.029(5) C13 0.079(6) 0.086(4) 0.136(7) -0.013(5) 0.006(5) -0.019(4) C12 0.102(7) 0.114(6) 0.068(6) -0.026(5) 0.000(5) -0.023(6) C7 0.066(6) 0.073(5) 0.056(5) -0.007(4) -0.005(4) -0.025(5) C17 0.091(6) 0.077(5) 0.103(6) -0.023(4) -0.022(4) -0.014(5) C14 0.100(7) 0.083(5) 0.112(6) -0.019(5) -0.033(5) -0.041(6) C25 0.064(5) 0.103(5) 0.074(5) -0.022(4) -0.007(4) -0.012(5) C1 0.096(7) 0.079(5) 0.093(6) -0.026(5) 0.030(5) -0.039(6) C23 0.081(6) 0.094(5) 0.100(6) -0.040(5) -0.023(4) -0.011(5) C4 0.086(6) 0.065(5) 0.094(6) -0.028(4) 0.023(5) -0.018(5) C15 0.123(8) 0.069(5) 0.112(6) -0.026(5) -0.042(6) -0.025(5) C2 0.090(7) 0.080(6) 0.080(6) -0.026(5) 0.013(5) -0.025(5) C26 0.110(6) 0.069(4) 0.193(7) -0.044(5) -0.054(5) -0.026(4) C24 0.073(6) 0.135(6) 0.111(7) -0.040(6) -0.016(5) -0.005(6) C10 0.091(6) 0.091(6) 0.088(6) -0.024(5) 0.013(5) -0.012(5) C11 0.095(6) 0.129(7) 0.105(7) -0.032(6) 0.021(5) 0.020(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C3 1.763(6) . ? Cl2 C16 1.752(6) . ? N3 C22 1.381(6) . ? N3 N4 1.394(5) . ? N3 C19 1.414(6) . ? N1 C9 1.354(7) . ? N1 N2 1.382(6) . ? N1 C6 1.440(7) . ? C21 C22 1.363(6) . ? C21 C20 1.398(6) . ? C21 C25 1.490(7) . ? N4 C20 1.329(6) . ? N2 C7 1.354(7) . ? C6 C5 1.356(7) . ? C6 C1 1.384(7) . ? C8 C9 1.356(7) . ? C8 C7 1.380(7) . ? C8 C12 1.495(8) . ? C19 C18 1.360(6) . ? C19 C14 1.389(6) . ? C3 C2 1.356(8) . ? C3 C4 1.368(7) . ? C20 C26 1.545(6) . ? C18 C17 1.381(7) . ? C18 H18A 0.9300 . ? C16 C15 1.360(8) . ? C16 C17 1.379(6) . ? C22 C23 1.493(6) . ? C5 C4 1.364(7) . ? C5 H5A 0.9300 . ? C9 C10 1.503(8) . ? C13 C7 1.516(7) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C12 C11 1.547(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C17 H17A 0.9300 . ? C14 C15 1.381(7) . ? C14 H14A 0.9300 . ? C25 C24 1.540(6) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C1 C2 1.401(8) . ? C1 H1A 0.9300 . ? C23 C24 1.557(7) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C4 H4A 0.9300 . ? C15 H15A 0.9300 . ? C2 H2A 0.9300 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C10 C11 1.564(8) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? 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 C22 N3 N4 109.5(4) . . ? C22 N3 C19 131.5(6) . . ? N4 N3 C19 118.9(6) . . ? C9 N1 N2 110.7(6) . . ? C9 N1 C6 129.2(7) . . ? N2 N1 C6 120.0(7) . . ? C22 C21 C20 103.8(5) . . ? C22 C21 C25 111.3(6) . . ? C20 C21 C25 145.0(6) . . ? C20 N4 N3 103.7(4) . . ? C7 N2 N1 103.7(6) . . ? C5 C6 C1 123.3(7) . . ? C5 C6 N1 117.8(7) . . ? C1 C6 N1 118.8(8) . . ? C9 C8 C7 105.9(7) . . ? C9 C8 C12 112.4(7) . . ? C7 C8 C12 141.7(8) . . ? C18 C19 C14 120.0(6) . . ? C18 C19 N3 119.6(6) . . ? C14 C19 N3 120.4(7) . . ? C2 C3 C4 121.4(7) . . ? C2 C3 Cl1 117.9(7) . . ? C4 C3 Cl1 120.7(7) . . ? N4 C20 C21 114.1(5) . . ? N4 C20 C26 120.1(6) . . ? C21 C20 C26 125.7(6) . . ? C19 C18 C17 122.0(6) . . ? C19 C18 H18A 119.0 . . ? C17 C18 H18A 119.0 . . ? C15 C16 C17 120.9(6) . . ? C15 C16 Cl2 119.8(6) . . ? C17 C16 Cl2 119.3(6) . . ? C21 C22 N3 108.9(5) . . ? C21 C22 C23 115.4(6) . . ? N3 C22 C23 135.7(6) . . ? C6 C5 C4 120.9(7) . . ? C6 C5 H5A 119.6 . . ? C4 C5 H5A 119.5 . . ? N1 C9 C8 108.0(7) . . ? N1 C9 C10 138.6(8) . . ? C8 C9 C10 113.4(8) . . ? C7 C13 H13A 109.5 . . ? C7 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C7 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C8 C12 C11 102.9(6) . . ? C8 C12 H12A 111.2 . . ? C11 C12 H12A 111.2 . . ? C8 C12 H12B 111.2 . . ? C11 C12 H12B 111.2 . . ? H12A C12 H12B 109.1 . . ? N2 C7 C8 111.7(6) . . ? N2 C7 C13 118.6(8) . . ? C8 C7 C13 129.5(8) . . ? C16 C17 C18 117.7(6) . . ? C16 C17 H17A 121.1 . . ? C18 C17 H17A 121.1 . . ? C15 C14 C19 118.0(6) . . ? C15 C14 H14A 121.0 . . ? C19 C14 H14A 121.0 . . ? C21 C25 C24 102.6(5) . . ? C21 C25 H25A 111.2 . . ? C24 C25 H25A 111.2 . . ? C21 C25 H25B 111.2 . . ? C24 C25 H25B 111.2 . . ? H25A C25 H25B 109.2 . . ? C6 C1 C2 114.4(7) . . ? C6 C1 H1A 122.8 . . ? C2 C1 H1A 122.8 . . ? C22 C23 C24 99.9(5) . . ? C22 C23 H23A 111.8 . . ? C24 C23 H23A 111.8 . . ? C22 C23 H23B 111.8 . . ? C24 C23 H23B 111.8 . . ? H23A C23 H23B 109.5 . . ? C5 C4 C3 117.8(7) . . ? C5 C4 H4A 121.1 . . ? C3 C4 H4A 121.1 . . ? C16 C15 C14 121.4(6) . . ? C16 C15 H15A 119.3 . . ? C14 C15 H15A 119.3 . . ? C3 C2 C1 122.3(7) . . ? C3 C2 H2A 118.9 . . ? C1 C2 H2A 118.9 . . ? C20 C26 H26A 109.5 . . ? C20 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C20 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C24 C23 110.4(5) . . ? C25 C24 H24A 109.6 . . ? C23 C24 H24A 109.6 . . ? C25 C24 H24B 109.6 . . ? C23 C24 H24B 109.6 . . ? H24A C24 H24B 108.1 . . ? C9 C10 C11 101.7(6) . . ? C9 C10 H10A 111.4 . . ? C11 C10 H10A 111.4 . . ? C9 C10 H10B 111.4 . . ? C11 C10 H10B 111.4 . . ? H10A C10 H10B 109.3 . . ? C12 C11 C10 108.4(6) . . ? C12 C11 H11A 110.0 . . ? C10 C11 H11A 110.0 . . ? C12 C11 H11B 110.0 . . ? C10 C11 H11B 110.0 . . ? H11A C11 H11B 108.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C22 N3 N4 C20 -1.4(6) . . . . ? C19 N3 N4 C20 -179.7(5) . . . . ? C9 N1 N2 C7 0.2(6) . . . . ? C6 N1 N2 C7 178.9(5) . . . . ? C9 N1 C6 C5 -169.7(6) . . . . ? N2 N1 C6 C5 12.0(7) . . . . ? C9 N1 C6 C1 11.2(8) . . . . ? N2 N1 C6 C1 -167.2(5) . . . . ? C22 N3 C19 C18 173.3(6) . . . . ? N4 N3 C19 C18 -8.8(7) . . . . ? C22 N3 C19 C14 -6.4(9) . . . . ? N4 N3 C19 C14 171.4(5) . . . . ? N3 N4 C20 C21 1.2(7) . . . . ? N3 N4 C20 C26 177.5(4) . . . . ? C22 C21 C20 N4 -0.5(7) . . . . ? C25 C21 C20 N4 178.5(8) . . . . ? C22 C21 C20 C26 -176.6(5) . . . . ? C25 C21 C20 C26 2.5(12) . . . . ? C14 C19 C18 C17 1.5(10) . . . . ? N3 C19 C18 C17 -178.3(6) . . . . ? C20 C21 C22 N3 -0.4(6) . . . . ? C25 C21 C22 N3 -179.8(5) . . . . ? C20 C21 C22 C23 -179.4(5) . . . . ? C25 C21 C22 C23 1.2(7) . . . . ? N4 N3 C22 C21 1.2(6) . . . . ? C19 N3 C22 C21 179.2(5) . . . . ? N4 N3 C22 C23 179.8(6) . . . . ? C19 N3 C22 C23 -2.2(11) . . . . ? C1 C6 C5 C4 0.6(10) . . . . ? N1 C6 C5 C4 -178.6(5) . . . . ? N2 N1 C9 C8 0.1(6) . . . . ? C6 N1 C9 C8 -178.4(5) . . . . ? N2 N1 C9 C10 -178.0(6) . . . . ? C6 N1 C9 C10 3.5(10) . . . . ? C7 C8 C9 N1 -0.4(6) . . . . ? C12 C8 C9 N1 -180.0(5) . . . . ? C7 C8 C9 C10 178.3(5) . . . . ? C12 C8 C9 C10 -1.4(7) . . . . ? C9 C8 C12 C11 7.6(7) . . . . ? C7 C8 C12 C11 -171.9(7) . . . . ? N1 N2 C7 C8 -0.5(7) . . . . ? N1 N2 C7 C13 -175.9(4) . . . . ? C9 C8 C7 N2 0.5(7) . . . . ? C12 C8 C7 N2 180.0(7) . . . . ? C9 C8 C7 C13 175.3(5) . . . . ? C12 C8 C7 C13 -5.2(12) . . . . ? C15 C16 C17 C18 0.2(9) . . . . ? Cl2 C16 C17 C18 -179.1(5) . . . . ? C19 C18 C17 C16 -1.3(9) . . . . ? C18 C19 C14 C15 -0.6(10) . . . . ? N3 C19 C14 C15 179.1(6) . . . . ? C22 C21 C25 C24 -4.7(7) . . . . ? C20 C21 C25 C24 176.3(8) . . . . ? C5 C6 C1 C2 -0.2(9) . . . . ? N1 C6 C1 C2 178.9(5) . . . . ? C21 C22 C23 C24 2.8(7) . . . . ? N3 C22 C23 C24 -175.8(7) . . . . ? C6 C5 C4 C3 -1.8(9) . . . . ? C2 C3 C4 C5 2.7(9) . . . . ? Cl1 C3 C4 C5 -178.6(4) . . . . ? C17 C16 C15 C14 0.6(11) . . . . ? Cl2 C16 C15 C14 179.9(6) . . . . ? C19 C14 C15 C16 -0.4(11) . . . . ? C4 C3 C2 C1 -2.4(10) . . . . ? Cl1 C3 C2 C1 178.8(5) . . . . ? C6 C1 C2 C3 1.1(9) . . . . ? C21 C25 C24 C23 6.4(7) . . . . ? C22 C23 C24 C25 -5.6(7) . . . . ? N1 C9 C10 C11 172.6(7) . . . . ? C8 C9 C10 C11 -5.4(7) . . . . ? C8 C12 C11 C10 -10.7(7) . . . . ? C9 C10 C11 C12 9.9(7) . . . . ? _diffrn_measured_fraction_theta_max 0.898 _diffrn_reflns_theta_full 29.29 _diffrn_measured_fraction_theta_full 0.898 _refine_diff_density_max 0.110 _refine_diff_density_min -0.106 _refine_diff_density_rms 0.027 data_a2 _database_code_depnum_ccdc_archive 'CCDC 850136' #TrackingRef '7761_web_deposit_cif_file_1_RezaKia_1319402141.2new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H8 Cl F3 N2 S' _chemical_formula_sum 'C14 H8 Cl F3 N2 S' _chemical_formula_weight 328.73 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' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _symmetry_space_group_name_Hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 25.542(5) _cell_length_b 9.4168(19) _cell_length_c 6.0399(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1452.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 4321 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 29.32 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.503 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.432 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8634 _exptl_absorpt_correction_T_max 0.9662 _exptl_absorpt_process_details 'MULABS (Blessing, 1995) in PLATON (Spek, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS 2T Image Plate diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean '0.15 mm' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 6269 _diffrn_reflns_av_R_equivalents 0.0652 _diffrn_reflns_av_sigmaI/netI 0.0915 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 29.20 _reflns_number_total 3222 _reflns_number_gt 1424 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area 1.52 (Stoe & Cie GmbH, 2009)' _computing_cell_refinement 'X-Area 1.52' _computing_data_reduction 'X-Area 1.52' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL, PLATON (Spek, 2009)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0745P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.08(11) _refine_ls_number_reflns 3222 _refine_ls_number_parameters 190 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1070 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1331 _refine_ls_wR_factor_gt 0.1211 _refine_ls_goodness_of_fit_ref 0.767 _refine_ls_restrained_S_all 0.767 _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 S1 S 0.70334(4) 0.90564(17) 0.86053(18) 0.0844(4) Uani 1 1 d . . . Cl1 Cl 0.44699(5) 0.58953(19) 1.5541(3) 0.1150(6) Uani 1 1 d . . . N1 N 0.61219(8) 1.0147(4) 1.3718(5) 0.0541(8) Uani 1 1 d . . . C12 C 0.49533(13) 0.7144(6) 1.4975(9) 0.0716(13) Uani 1 1 d . . . N2 N 0.61211(11) 1.1357(4) 1.4895(6) 0.0632(9) Uani 1 1 d . . . C6 C 0.65222(11) 0.7363(4) 1.1266(6) 0.0500(9) Uani 1 1 d . . . H6A H 0.6322 0.7010 1.2428 0.060 Uiso 1 1 calc R . . C3 C 0.68047(12) 1.1302(5) 1.2529(7) 0.0595(10) Uani 1 1 d . . . H3A H 0.7107 1.1572 1.1783 0.071 Uiso 1 1 calc R . . C5 C 0.66493(10) 0.8812(5) 1.0909(6) 0.0547(10) Uani 1 1 d . . . C4 C 0.65307(10) 1.0062(5) 1.2298(6) 0.0511(9) Uani 1 1 d . . . C9 C 0.57163(11) 0.9106(4) 1.4135(5) 0.0487(9) Uani 1 1 d . . . C13 C 0.49482(13) 0.7881(6) 1.3020(7) 0.0706(13) Uani 1 1 d . . . H13A H 0.4688 0.7716 1.1973 0.085 Uiso 1 1 calc R . . C10 C 0.57146(14) 0.8393(6) 1.6107(7) 0.0735(13) Uani 1 1 d . . . H10A H 0.5972 0.8582 1.7154 0.088 Uiso 1 1 calc R . . C14 C 0.53354(13) 0.8874(5) 1.2627(7) 0.0679(12) Uani 1 1 d . . . H14A H 0.5334 0.9387 1.1311 0.082 Uiso 1 1 calc R . . C11 C 0.53300(15) 0.7385(6) 1.6561(8) 0.0809(14) Uani 1 1 d . . . H11A H 0.5328 0.6890 1.7893 0.097 Uiso 1 1 calc R . . F1 F 0.62871(12) 1.4290(5) 1.5438(8) 0.1391(16) Uani 1 1 d . . . C8 C 0.70282(16) 0.7304(7) 0.8029(9) 0.0908(18) Uani 1 1 d . . . H8A H 0.7196 0.6910 0.6807 0.109 Uiso 1 1 calc R . . C2 C 0.65343(12) 1.2064(5) 1.4111(7) 0.0605(11) Uani 1 1 d . . . C7 C 0.67565(14) 0.6530(6) 0.9519(8) 0.0755(13) Uani 1 1 d . . . H7A H 0.6723 0.5548 0.9429 0.091 Uiso 1 1 calc R . . C1 C 0.66639(16) 1.3478(7) 1.5070(12) 0.0940(19) Uani 1 1 d . . . F3 F 0.6990(2) 1.4170(6) 1.3889(12) 0.213(3) Uani 1 1 d . . . F2 F 0.6905(2) 1.3351(5) 1.6944(9) 0.192(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0712(6) 0.0996(12) 0.0823(8) -0.0247(8) 0.0171(5) -0.0149(5) Cl1 0.0939(7) 0.1127(14) 0.1385(13) -0.0060(10) 0.0228(8) -0.0464(7) N1 0.0535(14) 0.051(2) 0.0574(18) -0.0126(18) 0.0021(13) -0.0001(13) C12 0.0570(18) 0.069(3) 0.089(3) -0.008(3) 0.010(2) -0.0089(17) N2 0.0694(16) 0.050(2) 0.070(2) -0.0236(19) 0.0038(15) 0.0012(15) C6 0.0508(15) 0.040(2) 0.059(2) -0.0294(19) 0.0027(15) 0.0031(13) C3 0.0594(18) 0.051(3) 0.068(3) -0.006(2) 0.0011(18) -0.0032(16) C5 0.0414(14) 0.070(3) 0.053(2) -0.015(2) -0.0001(13) -0.0014(14) C4 0.0476(16) 0.054(3) 0.052(2) -0.008(2) 0.0028(14) 0.0037(15) C9 0.0450(14) 0.057(3) 0.044(2) -0.004(2) 0.0073(13) -0.0002(14) C13 0.0528(18) 0.078(4) 0.081(3) 0.001(3) -0.0109(18) -0.0080(18) C10 0.070(2) 0.084(4) 0.066(3) -0.001(3) -0.0181(19) -0.019(2) C14 0.0610(19) 0.074(4) 0.069(3) 0.009(3) -0.0147(18) 0.0001(19) C11 0.086(3) 0.094(4) 0.063(3) 0.016(3) -0.003(2) -0.018(2) F1 0.126(2) 0.087(3) 0.205(4) -0.073(3) -0.034(2) 0.0233(18) C8 0.071(2) 0.113(5) 0.089(4) -0.054(3) 0.005(2) 0.002(2) C2 0.0574(17) 0.054(3) 0.070(3) -0.018(2) -0.0013(17) -0.0019(16) C7 0.071(2) 0.066(3) 0.090(3) -0.026(3) 0.001(2) -0.007(2) C1 0.071(2) 0.083(5) 0.128(5) -0.051(4) 0.005(3) -0.006(2) F3 0.264(5) 0.104(5) 0.271(7) -0.093(4) 0.135(5) -0.102(4) F2 0.259(5) 0.093(4) 0.224(6) -0.068(4) -0.148(5) 0.017(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C8 1.687(6) . ? S1 C5 1.718(4) . ? Cl1 C12 1.739(5) . ? N1 N2 1.343(5) . ? N1 C4 1.354(4) . ? N1 C9 1.448(5) . ? C12 C13 1.370(6) . ? C12 C11 1.376(6) . ? N2 C2 1.335(5) . ? C6 C5 1.418(6) . ? C6 C7 1.445(6) . ? C6 H6A 0.9300 . ? C3 C4 1.369(6) . ? C3 C2 1.380(6) . ? C3 H3A 0.9300 . ? C5 C4 1.477(6) . ? C9 C14 1.351(5) . ? C9 C10 1.368(6) . ? C13 C14 1.381(6) . ? C13 H13A 0.9300 . ? C10 C11 1.393(6) . ? C10 H10A 0.9300 . ? C14 H14A 0.9300 . ? C11 H11A 0.9300 . ? F1 C1 1.249(6) . ? C8 C7 1.350(8) . ? C8 H8A 0.9300 . ? C2 C1 1.489(7) . ? C7 H7A 0.9300 . ? C1 F3 1.276(8) . ? C1 F2 1.294(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 S1 C5 91.8(2) . . ? N2 N1 C4 112.8(3) . . ? N2 N1 C9 118.7(3) . . ? C4 N1 C9 128.4(3) . . ? C13 C12 C11 121.5(4) . . ? C13 C12 Cl1 120.4(3) . . ? C11 C12 Cl1 118.1(4) . . ? C2 N2 N1 103.5(3) . . ? C5 C6 C7 108.4(4) . . ? C5 C6 H6A 125.8 . . ? C7 C6 H6A 125.8 . . ? C4 C3 C2 105.0(3) . . ? C4 C3 H3A 127.5 . . ? C2 C3 H3A 127.5 . . ? C6 C5 C4 129.3(3) . . ? C6 C5 S1 112.5(3) . . ? C4 C5 S1 118.0(3) . . ? N1 C4 C3 106.2(3) . . ? N1 C4 C5 124.4(3) . . ? C3 C4 C5 129.3(3) . . ? C14 C9 C10 120.4(3) . . ? C14 C9 N1 120.5(3) . . ? C10 C9 N1 119.1(3) . . ? C12 C13 C14 119.0(4) . . ? C12 C13 H13A 120.5 . . ? C14 C13 H13A 120.5 . . ? C9 C10 C11 120.5(4) . . ? C9 C10 H10A 119.7 . . ? C11 C10 H10A 119.7 . . ? C9 C14 C13 120.6(4) . . ? C9 C14 H14A 119.7 . . ? C13 C14 H14A 119.7 . . ? C12 C11 C10 117.9(4) . . ? C12 C11 H11A 121.0 . . ? C10 C11 H11A 121.0 . . ? C7 C8 S1 113.2(4) . . ? C7 C8 H8A 123.4 . . ? S1 C8 H8A 123.4 . . ? N2 C2 C3 112.4(4) . . ? N2 C2 C1 118.9(4) . . ? C3 C2 C1 128.5(4) . . ? C8 C7 C6 114.0(5) . . ? C8 C7 H7A 123.0 . . ? C6 C7 H7A 123.0 . . ? F1 C1 F3 106.8(7) . . ? F1 C1 F2 105.5(5) . . ? F3 C1 F2 103.0(5) . . ? F1 C1 C2 116.4(4) . . ? F3 C1 C2 112.6(5) . . ? F2 C1 C2 111.3(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 N2 C2 2.3(4) . . . . ? C9 N1 N2 C2 -179.7(3) . . . . ? C7 C6 C5 C4 -175.9(3) . . . . ? C7 C6 C5 S1 -0.7(3) . . . . ? C8 S1 C5 C6 1.0(3) . . . . ? C8 S1 C5 C4 176.8(3) . . . . ? N2 N1 C4 C3 -1.4(4) . . . . ? C9 N1 C4 C3 -179.3(3) . . . . ? N2 N1 C4 C5 175.7(3) . . . . ? C9 N1 C4 C5 -2.1(5) . . . . ? C2 C3 C4 N1 0.0(4) . . . . ? C2 C3 C4 C5 -177.0(4) . . . . ? C6 C5 C4 N1 -26.0(5) . . . . ? S1 C5 C4 N1 159.1(3) . . . . ? C6 C5 C4 C3 150.4(4) . . . . ? S1 C5 C4 C3 -24.5(5) . . . . ? N2 N1 C9 C14 109.3(4) . . . . ? C4 N1 C9 C14 -73.0(5) . . . . ? N2 N1 C9 C10 -68.7(5) . . . . ? C4 N1 C9 C10 109.0(4) . . . . ? C11 C12 C13 C14 0.9(7) . . . . ? Cl1 C12 C13 C14 179.5(4) . . . . ? C14 C9 C10 C11 2.0(7) . . . . ? N1 C9 C10 C11 -180.0(4) . . . . ? C10 C9 C14 C13 -2.1(6) . . . . ? N1 C9 C14 C13 180.0(4) . . . . ? C12 C13 C14 C9 0.6(7) . . . . ? C13 C12 C11 C10 -1.0(8) . . . . ? Cl1 C12 C11 C10 -179.6(4) . . . . ? C9 C10 C11 C12 -0.5(8) . . . . ? C5 S1 C8 C7 -1.1(4) . . . . ? N1 N2 C2 C3 -2.2(4) . . . . ? N1 N2 C2 C1 -179.1(4) . . . . ? C4 C3 C2 N2 1.5(5) . . . . ? C4 C3 C2 C1 178.0(5) . . . . ? S1 C8 C7 C6 0.9(5) . . . . ? C5 C6 C7 C8 -0.1(5) . . . . ? N2 C2 C1 F1 -42.0(9) . . . . ? C3 C2 C1 F1 141.7(6) . . . . ? N2 C2 C1 F3 -165.9(6) . . . . ? C3 C2 C1 F3 17.8(10) . . . . ? N2 C2 C1 F2 78.9(6) . . . . ? C3 C2 C1 F2 -97.4(7) . . . . ? _diffrn_measured_fraction_theta_max 0.921 _diffrn_reflns_theta_full 29.20 _diffrn_measured_fraction_theta_full 0.921 _refine_diff_density_max 0.266 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.047 data_a3 _database_code_depnum_ccdc_archive 'CCDC 850137' #TrackingRef '7762_web_deposit_cif_file_2_RezaKia_1319402141.SS1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H8 F3 N3 O S' _chemical_formula_sum 'C6 H8 F3 N3 O S' _chemical_formula_weight 227.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 2/c' _symmetry_space_group_name_Hall '-P 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 11.767(2) _cell_length_b 6.7984(14) _cell_length_c 13.303(3) _cell_angle_alpha 90.00 _cell_angle_beta 115.03(3) _cell_angle_gamma 90.00 _cell_volume 964.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 2350 _cell_measurement_theta_min 2.78 _cell_measurement_theta_max 29.59 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.565 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.353 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.978 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'MULABS (Blessing, 1995) in PLATON (Spek, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS 2T Image Plate diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean '0.15 mm' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 4251 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.0635 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1766 _reflns_number_gt 1020 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area 1.52 (Stoe & Cie GmbH, 2009)' _computing_cell_refinement 'X-Area 1.52' _computing_data_reduction 'X-Area 1.52' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL, PLATON (Spek, 2009)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0339P)^2^] 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 1766 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0713 _refine_ls_R_factor_gt 0.0323 _refine_ls_wR_factor_ref 0.0662 _refine_ls_wR_factor_gt 0.0605 _refine_ls_goodness_of_fit_ref 0.795 _refine_ls_restrained_S_all 0.795 _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 S1 S 0.55355(6) -0.21071(9) -0.42318(4) 0.0558(2) Uani 1 1 d . . . F1 F 0.82325(15) -0.0296(3) -0.30111(10) 0.0898(5) Uani 1 1 d . . . F2 F 0.89474(16) 0.1286(2) -0.14820(12) 0.0900(5) Uani 1 1 d . . . F3 F 0.94064(14) -0.1740(3) -0.14945(13) 0.0898(5) Uani 1 1 d . . . O1 O 0.64133(14) 0.0403(2) -0.21721(10) 0.0525(4) Uani 1 1 d . . . H1 H 0.6005 0.0057 -0.2865 0.079 Uiso 1 1 d R . . N1 N 0.69508(17) -0.3021(3) -0.21089(11) 0.0444(5) Uani 1 1 d . . . N2 N 0.73528(17) -0.4392(3) -0.12175(12) 0.0500(5) Uani 1 1 d . . . N3 N 0.5912(2) -0.5559(3) -0.32275(13) 0.0604(6) Uani 1 1 d . . . H2 H 0.6261 -0.6329 -0.2637 0.073 Uiso 1 1 d R . . H3 H 0.5460 -0.5939 -0.3827 0.073 Uiso 1 1 d R . . C1 C 0.7823(2) -0.3400(3) -0.03139(15) 0.0482(6) Uani 1 1 d . . . C2 C 0.7761(2) -0.1240(3) -0.04659(14) 0.0489(6) Uani 1 1 d . . . H2A H 0.8574 -0.0639 -0.0047 0.059 Uiso 1 1 calc R . . H2B H 0.7155 -0.0660 -0.0237 0.059 Uiso 1 1 calc R . . C3 C 0.7348(2) -0.0996(3) -0.17188(14) 0.0409(6) Uani 1 1 d . . . C4 C 0.6160(2) -0.3666(3) -0.31366(14) 0.0445(6) Uani 1 1 d . . . C5 C 0.8374(3) -0.4415(4) 0.07907(16) 0.0744(9) Uani 1 1 d . . . H5A H 0.8196 -0.5797 0.0688 0.112 Uiso 1 1 calc R . . H5B H 0.8014 -0.3880 0.1258 0.112 Uiso 1 1 calc R . . H5C H 0.9265 -0.4218 0.1133 0.112 Uiso 1 1 calc R . . C6 C 0.8479(3) -0.0451(4) -0.19427(17) 0.0603(7) 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 S1 0.0704(5) 0.0420(3) 0.0379(3) 0.0022(2) 0.0063(2) 0.0029(3) F1 0.0841(12) 0.1288(14) 0.0596(8) 0.0127(8) 0.0334(7) -0.0245(11) F2 0.0808(12) 0.0818(12) 0.0958(10) -0.0065(9) 0.0262(8) -0.0433(10) F3 0.0564(11) 0.1108(14) 0.1051(11) 0.0251(10) 0.0371(9) 0.0169(10) O1 0.0535(10) 0.0336(9) 0.0523(8) -0.0034(6) 0.0048(7) 0.0061(8) N1 0.0566(13) 0.0293(10) 0.0355(8) 0.0030(7) 0.0082(7) 0.0005(10) N2 0.0594(13) 0.0387(11) 0.0427(9) 0.0084(8) 0.0125(8) 0.0009(10) N3 0.0830(16) 0.0356(13) 0.0441(9) -0.0048(8) 0.0088(9) -0.0064(11) C1 0.0486(15) 0.0486(16) 0.0393(11) 0.0040(10) 0.0107(9) -0.0054(12) C2 0.0488(15) 0.0518(15) 0.0384(10) -0.0062(10) 0.0109(9) -0.0062(12) C3 0.0435(15) 0.0317(13) 0.0398(10) -0.0007(9) 0.0101(9) -0.0018(11) C4 0.0523(15) 0.0359(14) 0.0384(10) -0.0018(9) 0.0126(10) 0.0022(11) C5 0.089(2) 0.0753(19) 0.0441(11) 0.0157(12) 0.0137(12) -0.0099(17) C6 0.0553(18) 0.0652(18) 0.0538(13) 0.0085(12) 0.0166(12) -0.0062(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C4 1.697(2) . ? F1 C6 1.329(2) . ? F2 C6 1.337(3) . ? F3 C6 1.328(3) . ? O1 C3 1.385(2) . ? O1 H1 0.8718 . ? N1 C4 1.360(2) . ? N1 N2 1.422(2) . ? N1 C3 1.476(2) . ? N2 C1 1.282(2) . ? N3 C4 1.314(3) . ? N3 H2 0.8866 . ? N3 H3 0.7922 . ? C1 C2 1.480(3) . ? C1 C5 1.500(3) . ? C2 C3 1.535(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C6 1.527(3) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 H1 104.8 . . ? C4 N1 N2 118.14(18) . . ? C4 N1 C3 129.36(16) . . ? N2 N1 C3 111.95(14) . . ? C1 N2 N1 107.25(17) . . ? C4 N3 H2 119.7 . . ? C4 N3 H3 116.1 . . ? H2 N3 H3 124.2 . . ? N2 C1 C2 114.65(16) . . ? N2 C1 C5 120.9(2) . . ? C2 C1 C5 124.49(18) . . ? C1 C2 C3 103.30(16) . . ? C1 C2 H2A 111.1 . . ? C3 C2 H2A 111.1 . . ? C1 C2 H2B 111.1 . . ? C3 C2 H2B 111.1 . . ? H2A C2 H2B 109.1 . . ? O1 C3 N1 114.36(16) . . ? O1 C3 C6 110.23(18) . . ? N1 C3 C6 109.29(19) . . ? O1 C3 C2 112.03(18) . . ? N1 C3 C2 100.89(15) . . ? C6 C3 C2 109.64(17) . . ? N3 C4 N1 116.03(17) . . ? N3 C4 S1 122.28(15) . . ? N1 C4 S1 121.69(17) . . ? C1 C5 H5A 109.5 . . ? C1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? F3 C6 F1 107.4(2) . . ? F3 C6 F2 106.0(2) . . ? F1 C6 F2 106.3(2) . . ? F3 C6 C3 111.8(2) . . ? F1 C6 C3 114.45(19) . . ? F2 C6 C3 110.4(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 N2 C1 -164.7(2) . . . . ? C3 N1 N2 C1 7.5(3) . . . . ? N1 N2 C1 C2 2.2(3) . . . . ? N1 N2 C1 C5 -178.2(2) . . . . ? N2 C1 C2 C3 -10.3(3) . . . . ? C5 C1 C2 C3 170.1(2) . . . . ? C4 N1 C3 O1 37.7(3) . . . . ? N2 N1 C3 O1 -133.49(18) . . . . ? C4 N1 C3 C6 -86.5(3) . . . . ? N2 N1 C3 C6 102.41(19) . . . . ? C4 N1 C3 C2 158.1(2) . . . . ? N2 N1 C3 C2 -13.1(2) . . . . ? C1 C2 C3 O1 135.1(2) . . . . ? C1 C2 C3 N1 13.0(2) . . . . ? C1 C2 C3 C6 -102.2(2) . . . . ? N2 N1 C4 N3 -5.0(3) . . . . ? C3 N1 C4 N3 -175.7(2) . . . . ? N2 N1 C4 S1 175.02(16) . . . . ? C3 N1 C4 S1 4.3(3) . . . . ? O1 C3 C6 F3 178.45(17) . . . . ? N1 C3 C6 F3 -55.1(2) . . . . ? C2 C3 C6 F3 54.7(2) . . . . ? O1 C3 C6 F1 -59.2(3) . . . . ? N1 C3 C6 F1 67.3(3) . . . . ? C2 C3 C6 F1 177.0(2) . . . . ? O1 C3 C6 F2 60.7(2) . . . . ? N1 C3 C6 F2 -172.81(16) . . . . ? C2 C3 C6 F2 -63.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.928 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.928 _refine_diff_density_max 0.140 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.039 #======================== #END OF CIF