# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_CEL-2PY _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Celecoxib-2-Pyrrolidinone _chemical_melting_point 403 _chemical_formula_moiety 'C17 H14 F3 N3 O2 S, C4 H7 N O' _chemical_formula_sum 'C21 H21 F3 N4 O3 S' _chemical_formula_weight 466.48 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.0368(5) _cell_length_b 8.6083(4) _cell_length_c 12.0762(6) _cell_angle_alpha 90.00 _cell_angle_beta 109.049(5) _cell_angle_gamma 90.00 _cell_volume 1084.51(9) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1867 _cell_measurement_theta_min 2.9578 _cell_measurement_theta_max 26.3148 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 0.206 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.93761 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4337 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -3 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2656 _reflns_number_gt 2351 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0514P)^2^+0.3791P] 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 mixed _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 0.06(12) _refine_ls_number_reflns 2656 _refine_ls_number_parameters 296 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0509 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1109 _refine_ls_wR_factor_gt 0.1047 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.33959(8) 0.16713(12) 0.04015(7) 0.0457(2) Uani 1 1 d . . . N2 N 0.5223(2) 0.1500(4) 0.5619(2) 0.0461(7) Uani 1 1 d . . . C15 C 0.3913(3) 0.1619(5) 0.1955(3) 0.0430(7) Uani 1 1 d . . . N1 N 0.6494(2) 0.1772(5) 0.6122(2) 0.0491(7) Uani 1 1 d . . . C3 C 0.4608(3) 0.1337(4) 0.6430(3) 0.0461(9) Uani 1 1 d . . . C5 C 0.3234(3) 0.1006(5) 0.6142(3) 0.0468(8) Uani 1 1 d . . . C10 C 0.2546(3) 0.1692(6) 0.6788(3) 0.0523(8) Uani 1 1 d . . . H10 H 0.2964 0.2342 0.7410 0.063 Uiso 1 1 calc R . . O2 O 0.2127(2) 0.2280(4) 0.0016(2) 0.0619(8) Uani 1 1 d . . . O1 O 0.3641(3) 0.0156(4) 0.0034(3) 0.0624(8) Uani 1 1 d . . . N3 N 0.4272(4) 0.2845(5) -0.0005(3) 0.0535(8) Uani 1 1 d . . . H3B H 0.418(4) 0.383(6) 0.007(4) 0.064 Uiso 1 1 d . . . H3A H 0.509(4) 0.252(6) 0.018(4) 0.064 Uiso 1 1 d . . . C17 C 0.3702(3) 0.2443(5) 0.3770(3) 0.0515(9) Uani 1 1 d . . . H17 H 0.3282 0.3021 0.4186 0.062 Uiso 1 1 calc R . . C2 C 0.5532(3) 0.1517(6) 0.7501(3) 0.0495(8) Uani 1 1 d . . . H2 H 0.5425 0.1471 0.8234 0.059 Uiso 1 1 calc R . . C1 C 0.6667(3) 0.1785(6) 0.7260(3) 0.0489(8) Uani 1 1 d . . . C12 C 0.4742(3) 0.1542(5) 0.4363(3) 0.0449(8) Uani 1 1 d . . . F2 F 0.8780(2) 0.2516(6) 0.7586(2) 0.1205(16) Uani 1 1 d . . . C16 C 0.3281(3) 0.2489(5) 0.2566(3) 0.0490(9) Uani 1 1 d . . . H16 H 0.2579 0.3098 0.2164 0.059 Uiso 1 1 calc R . . F1 F 0.8003(3) 0.3057(5) 0.8896(3) 0.1086(13) Uani 1 1 d . . . C14 C 0.4962(4) 0.0732(5) 0.2547(3) 0.0519(9) Uani 1 1 d . . . H14 H 0.5385 0.0154 0.2134 0.062 Uiso 1 1 calc R . . C13 C 0.5383(4) 0.0705(5) 0.3753(3) 0.0532(10) Uani 1 1 d . . . H13 H 0.6100 0.0121 0.4157 0.064 Uiso 1 1 calc R . . C8 C 0.0601(4) 0.0463(5) 0.5604(3) 0.0548(10) Uani 1 1 d . . . C4 C 0.7973(4) 0.2064(5) 0.8076(3) 0.0559(11) Uani 1 1 d . . . C7 C 0.1295(4) -0.0275(5) 0.4995(4) 0.0595(10) Uani 1 1 d . . . H7 H 0.0879 -0.0960 0.4396 0.071 Uiso 1 1 calc R . . F3 F 0.8489(3) 0.0798(5) 0.8667(4) 0.1300(15) Uani 1 1 d . . . C11 C -0.0835(4) 0.0216(7) 0.5260(4) 0.0746(14) Uani 1 1 d . . . H11A H -0.1252 0.0715 0.4523 0.112 Uiso 1 1 calc R . . H11B H -0.1143 0.0653 0.5850 0.112 Uiso 1 1 calc R . . H11C H -0.1019 -0.0877 0.5191 0.112 Uiso 1 1 calc R . . C9 C 0.1255(3) 0.1427(6) 0.6523(3) 0.0564(11) Uani 1 1 d . . . H9 H 0.0813 0.1903 0.6968 0.068 Uiso 1 1 calc R . . C6 C 0.2593(4) -0.0021(5) 0.5255(3) 0.0562(10) Uani 1 1 d . . . H6 H 0.3041 -0.0538 0.4835 0.067 Uiso 1 1 calc R . . O3 O 0.6610(3) 0.1006(4) 0.0662(3) 0.0698(8) Uani 1 1 d . . . C18 C 0.7742(4) 0.1323(5) 0.1182(3) 0.0542(10) Uani 1 1 d . . . C21 C 0.9980(5) 0.1152(8) 0.1813(6) 0.0962(19) Uani 1 1 d . . . H21A H 1.0399 0.1237 0.1223 0.115 Uiso 1 1 calc R . . H21B H 1.0546 0.0612 0.2489 0.115 Uiso 1 1 calc R . . C19 C 0.8240(5) 0.2788(6) 0.1693(6) 0.0945(19) Uani 1 1 d . . . H19A H 0.7911 0.3032 0.2325 0.113 Uiso 1 1 calc R . . H19B H 0.7975 0.3602 0.1108 0.113 Uiso 1 1 calc R . . N4 N 0.8754(4) 0.0345(6) 0.1347(4) 0.0872(13) Uani 1 1 d . . . H4A H 0.8680 -0.0633 0.1195 0.105 Uiso 1 1 calc R . . C20 C 0.9637(6) 0.2694(10) 0.2142(8) 0.143(3) Uani 1 1 d . . . H20A H 0.9944 0.2816 0.2986 0.172 Uiso 1 1 calc R . . H20B H 1.0013 0.3504 0.1799 0.172 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 0.0464(4) 0.0467(5) 0.0416(4) 0.0011(5) 0.0110(3) -0.0033(5) N2 0.0464(14) 0.0540(19) 0.0414(13) 0.0050(16) 0.0189(11) 0.0030(16) C15 0.0434(15) 0.0442(18) 0.0425(15) 0.0030(19) 0.0156(13) -0.0033(19) N1 0.0437(14) 0.060(2) 0.0460(14) 0.0018(18) 0.0173(11) -0.0007(17) C3 0.0504(18) 0.048(3) 0.0454(17) 0.0035(17) 0.0236(15) 0.0021(17) C5 0.0472(18) 0.052(2) 0.0451(18) 0.0037(17) 0.0209(15) 0.0027(18) C10 0.0549(18) 0.060(2) 0.0443(16) -0.005(2) 0.0195(14) 0.003(2) O2 0.0460(13) 0.077(2) 0.0548(14) 0.0093(15) 0.0063(11) 0.0009(14) O1 0.0745(19) 0.0491(17) 0.0601(17) -0.0123(14) 0.0171(14) -0.0066(15) N3 0.0556(19) 0.051(2) 0.0575(19) 0.0072(17) 0.0229(16) 0.0013(18) C17 0.054(2) 0.052(2) 0.052(2) -0.0075(19) 0.0231(16) 0.0087(19) C2 0.0547(18) 0.054(2) 0.0437(16) -0.002(2) 0.0216(15) 0.001(2) C1 0.0535(18) 0.050(2) 0.0450(17) 0.000(2) 0.0192(14) 0.004(2) C12 0.0448(16) 0.047(2) 0.0443(16) 0.003(2) 0.0173(13) -0.001(2) F2 0.0681(15) 0.225(5) 0.0714(16) -0.015(2) 0.0272(13) -0.049(2) C16 0.0484(18) 0.050(2) 0.0475(19) 0.0021(17) 0.0146(15) 0.0096(18) F1 0.0821(19) 0.140(3) 0.091(2) -0.059(2) 0.0111(15) 0.001(2) C14 0.056(2) 0.061(3) 0.0454(19) 0.0082(19) 0.0252(16) 0.017(2) C13 0.052(2) 0.065(3) 0.0457(19) 0.0146(19) 0.0207(16) 0.019(2) C8 0.051(2) 0.056(2) 0.059(2) 0.003(2) 0.0191(18) 0.0065(19) C4 0.056(2) 0.069(3) 0.0430(18) -0.0044(19) 0.0171(16) -0.002(2) C7 0.062(2) 0.062(3) 0.056(2) -0.010(2) 0.0228(19) -0.009(2) F3 0.087(2) 0.089(2) 0.158(3) 0.012(3) -0.038(2) 0.000(2) C11 0.055(2) 0.085(4) 0.083(3) -0.003(3) 0.020(2) -0.002(3) C9 0.0513(19) 0.067(3) 0.058(2) -0.006(2) 0.0275(17) 0.006(2) C6 0.063(2) 0.054(3) 0.060(2) -0.009(2) 0.032(2) -0.001(2) O3 0.0524(16) 0.0609(19) 0.097(2) -0.0134(17) 0.0255(15) -0.0035(15) C18 0.054(2) 0.056(3) 0.052(2) -0.0007(19) 0.0169(17) -0.002(2) C21 0.057(3) 0.092(5) 0.119(4) 0.010(4) 0.000(3) 0.004(3) C19 0.069(3) 0.046(3) 0.162(6) -0.018(3) 0.029(3) 0.003(3) N4 0.071(3) 0.055(2) 0.131(4) -0.008(3) 0.027(3) -0.004(2) C20 0.072(4) 0.105(6) 0.228(9) -0.073(6) 0.016(4) -0.019(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.424(3) . ? S1 O1 1.432(3) . ? S1 N3 1.583(4) . ? S1 C15 1.774(3) . ? N2 N1 1.355(4) . ? N2 C3 1.369(4) . ? N2 C12 1.435(4) . ? C15 C14 1.376(5) . ? C15 C16 1.388(5) . ? N1 C1 1.324(4) . ? C3 C2 1.371(5) . ? C3 C5 1.469(5) . ? C5 C10 1.385(5) . ? C5 C6 1.391(5) . ? C10 C9 1.373(5) . ? C10 H10 0.9300 . ? N3 H3B 0.86(5) . ? N3 H3A 0.90(4) . ? C17 C16 1.376(5) . ? C17 C12 1.377(5) . ? C17 H17 0.9300 . ? C2 C1 1.395(5) . ? C2 H2 0.9300 . ? C1 C4 1.476(5) . ? C12 C13 1.379(5) . ? F2 C4 1.281(4) . ? C16 H16 0.9300 . ? F1 C4 1.300(5) . ? C14 C13 1.377(5) . ? C14 H14 0.9300 . ? C13 H13 0.9300 . ? C8 C7 1.378(5) . ? C8 C9 1.385(6) . ? C8 C11 1.517(5) . ? C4 F3 1.325(6) . ? C7 C6 1.381(5) . ? C7 H7 0.9300 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C9 H9 0.9300 . ? C6 H6 0.9300 . ? O3 C18 1.232(4) . ? C18 N4 1.360(6) . ? C18 C19 1.432(7) . ? C21 N4 1.461(7) . ? C21 C20 1.470(9) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C19 C20 1.460(7) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? N4 H4A 0.8600 . ? C20 H20A 0.9700 . ? C20 H20B 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 O2 S1 O1 119.92(18) . . ? O2 S1 N3 107.4(2) . . ? O1 S1 N3 106.8(2) . . ? O2 S1 C15 107.33(16) . . ? O1 S1 C15 106.0(2) . . ? N3 S1 C15 109.01(19) . . ? N1 N2 C3 112.3(3) . . ? N1 N2 C12 116.2(2) . . ? C3 N2 C12 131.3(3) . . ? C14 C15 C16 120.5(3) . . ? C14 C15 S1 119.3(3) . . ? C16 C15 S1 120.3(3) . . ? C1 N1 N2 104.1(2) . . ? N2 C3 C2 105.9(3) . . ? N2 C3 C5 124.5(3) . . ? C2 C3 C5 129.6(3) . . ? C10 C5 C6 118.0(3) . . ? C10 C5 C3 119.8(3) . . ? C6 C5 C3 122.1(3) . . ? C9 C10 C5 121.1(4) . . ? C9 C10 H10 119.5 . . ? C5 C10 H10 119.5 . . ? S1 N3 H3B 120(3) . . ? S1 N3 H3A 113(3) . . ? H3B N3 H3A 115(4) . . ? C16 C17 C12 120.1(3) . . ? C16 C17 H17 119.9 . . ? C12 C17 H17 119.9 . . ? C3 C2 C1 105.3(3) . . ? C3 C2 H2 127.4 . . ? C1 C2 H2 127.4 . . ? N1 C1 C2 112.4(3) . . ? N1 C1 C4 118.2(3) . . ? C2 C1 C4 129.4(3) . . ? C17 C12 C13 120.2(3) . . ? C17 C12 N2 121.4(3) . . ? C13 C12 N2 118.3(3) . . ? C17 C16 C15 119.4(3) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C15 C14 C13 119.7(3) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C13 C12 120.1(3) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C7 C8 C9 118.0(4) . . ? C7 C8 C11 120.2(4) . . ? C9 C8 C11 121.9(4) . . ? F2 C4 F1 107.7(4) . . ? F2 C4 F3 104.9(4) . . ? F1 C4 F3 103.3(3) . . ? F2 C4 C1 114.6(3) . . ? F1 C4 C1 113.1(3) . . ? F3 C4 C1 112.3(4) . . ? C8 C7 C6 121.5(4) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C9 C8 121.0(3) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C7 C6 C5 120.3(4) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? O3 C18 N4 125.8(4) . . ? O3 C18 C19 126.7(4) . . ? N4 C18 C19 107.5(4) . . ? N4 C21 C20 104.2(5) . . ? N4 C21 H21A 110.9 . . ? C20 C21 H21A 110.9 . . ? N4 C21 H21B 110.9 . . ? C20 C21 H21B 110.9 . . ? H21A C21 H21B 108.9 . . ? C18 C19 C20 108.7(5) . . ? C18 C19 H19A 109.9 . . ? C20 C19 H19A 109.9 . . ? C18 C19 H19B 109.9 . . ? C20 C19 H19B 109.9 . . ? H19A C19 H19B 108.3 . . ? C18 N4 C21 112.0(4) . . ? C18 N4 H4A 124.0 . . ? C21 N4 H4A 124.0 . . ? C19 C20 C21 106.5(5) . . ? C19 C20 H20A 110.4 . . ? C21 C20 H20A 110.4 . . ? C19 C20 H20B 110.4 . . ? C21 C20 H20B 110.4 . . ? H20A C20 H20B 108.6 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.278 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 954140' ####################################################################### # # 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_CEL-AZL _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Celecoxib-Aza-2-cyclooctanone _chemical_melting_point 381 _chemical_formula_moiety 'C17 H14 F3 N3 O2 S, C7 H13 N O' _chemical_formula_sum 'C24 H27 F3 N4 O3 S' _chemical_formula_weight 508.56 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 monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.0409(5) _cell_length_b 27.2426(18) _cell_length_c 11.7927(8) _cell_angle_alpha 90.00 _cell_angle_beta 105.806(7) _cell_angle_gamma 90.00 _cell_volume 2485.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3115 _cell_measurement_theta_min 2.8471 _cell_measurement_theta_max 26.3145 _exptl_crystal_description PLATE _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 0.186 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.88294 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9351 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0718 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 24.71 _reflns_number_total 4244 _reflns_number_gt 2455 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.1322P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4244 _refine_ls_number_parameters 323 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1211 _refine_ls_R_factor_gt 0.0760 _refine_ls_wR_factor_ref 0.2281 _refine_ls_wR_factor_gt 0.2099 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 O3 O 0.3021(5) 0.47406(14) -0.0776(3) 0.0684(10) Uani 1 1 d . . . S1 S 1.15737(13) 0.44068(4) 0.61060(10) 0.0426(4) Uani 1 1 d . . . O2 O 1.1201(4) 0.45273(12) 0.4883(3) 0.0534(9) Uani 1 1 d . . . N2 N 0.5530(5) 0.32550(13) 0.6637(3) 0.0444(9) Uani 1 1 d . . . C15 C 0.9797(5) 0.40599(16) 0.6301(4) 0.0393(10) Uani 1 1 d . . . N3 N 1.1614(5) 0.49167(15) 0.6789(3) 0.0484(10) Uani 1 1 d . . . O1 O 1.3114(4) 0.41489(13) 0.6657(3) 0.0609(10) Uani 1 1 d . . . N1 N 0.4400(5) 0.31318(14) 0.5605(3) 0.0503(10) Uani 1 1 d . . . C12 C 0.7011(5) 0.35410(15) 0.6583(4) 0.0389(10) Uani 1 1 d . . . C14 C 1.0041(5) 0.37105(17) 0.7156(4) 0.0466(11) Uani 1 1 d . . . H14 H 1.1142 0.3652 0.7648 0.056 Uiso 1 1 calc R . . C13 C 0.8629(6) 0.34395(17) 0.7294(4) 0.0489(12) Uani 1 1 d . . . H13 H 0.8788 0.3194 0.7860 0.059 Uiso 1 1 calc R . . C16 C 0.8146(5) 0.41634(16) 0.5592(4) 0.0435(11) Uani 1 1 d . . . H16 H 0.7988 0.4410 0.5028 0.052 Uiso 1 1 calc R . . C3 C 0.5094(6) 0.30762(15) 0.7605(4) 0.0468(11) Uani 1 1 d . . . C5 C 0.5957(6) 0.32067(17) 0.8836(4) 0.0481(12) Uani 1 1 d . . . C17 C 0.6744(5) 0.39016(16) 0.5724(4) 0.0462(11) Uani 1 1 d . . . H17 H 0.5640 0.3966 0.5245 0.055 Uiso 1 1 calc R . . C10 C 0.6165(6) 0.36922(18) 0.9197(4) 0.0554(13) Uani 1 1 d . . . H10 H 0.5867 0.3940 0.8636 0.066 Uiso 1 1 calc R . . C9 C 0.6801(6) 0.3816(2) 1.0364(4) 0.0584(13) Uani 1 1 d . . . H9 H 0.6917 0.4146 1.0576 0.070 Uiso 1 1 calc R . . C8 C 0.7275(6) 0.3459(2) 1.1236(4) 0.0566(13) Uani 1 1 d . . . C2 C 0.3619(6) 0.28115(18) 0.7166(5) 0.0593(14) Uani 1 1 d . . . H2 H 0.3007 0.2635 0.7593 0.071 Uiso 1 1 calc R . . C1 C 0.3216(6) 0.28604(17) 0.5938(5) 0.0544(13) Uani 1 1 d . . . C6 C 0.6421(7) 0.2847(2) 0.9692(5) 0.0660(15) Uani 1 1 d . . . H6 H 0.6288 0.2518 0.9475 0.079 Uiso 1 1 calc R . . C7 C 0.7085(7) 0.2971(2) 1.0875(5) 0.0706(16) Uani 1 1 d . . . H7 H 0.7408 0.2723 1.1433 0.085 Uiso 1 1 calc R . . C11 C 0.7927(8) 0.3597(3) 1.2522(5) 0.0871(19) Uani 1 1 d . . . H11A H 0.8988 0.3427 1.2871 0.131 Uiso 1 1 calc R . . H11B H 0.7081 0.3508 1.2924 0.131 Uiso 1 1 calc R . . H11C H 0.8125 0.3945 1.2589 0.131 Uiso 1 1 calc R . . F2 F 0.1964(8) 0.22287(19) 0.4690(5) 0.166(2) Uani 1 1 d . . . F3 F 0.1488(6) 0.28540(19) 0.3962(5) 0.1474(18) Uani 1 1 d . . . C4 C 0.1705(9) 0.2686(3) 0.5041(6) 0.087(2) Uani 1 1 d . . . F1 F 0.0407(7) 0.2672(4) 0.5309(6) 0.303(6) Uani 1 1 d . . . N4 N 0.3574(5) 0.49448(14) 0.1116(3) 0.0528(10) Uani 1 1 d D . . H4A H 0.4478 0.5093 0.1033 0.063 Uiso 1 1 calc RD . . C24 C 0.2623(6) 0.47245(17) 0.0172(4) 0.0488(12) Uani 1 1 d . . . C23 C 0.1080(6) 0.44333(18) 0.0262(5) 0.0566(13) Uani 1 1 d . . . H23A H 0.0190 0.4451 -0.0482 0.068 Uiso 1 1 calc R . . H23B H 0.0617 0.4575 0.0866 0.068 Uiso 1 1 calc R . . C22 C 0.1546(7) 0.38956(18) 0.0563(5) 0.0629(14) Uani 1 1 d . . . H22A H 0.1874 0.3747 -0.0092 0.075 Uiso 1 1 calc R . . H22B H 0.0525 0.3726 0.0645 0.075 Uiso 1 1 calc R . . C18 C 0.3299(7) 0.49723(19) 0.2295(4) 0.0600(14) Uani 1 1 d . . . H18A H 0.2071 0.5012 0.2206 0.072 Uiso 1 1 calc R . . H18B H 0.3873 0.5264 0.2684 0.072 Uiso 1 1 calc R . . C19 C 0.3929(7) 0.4537(2) 0.3089(4) 0.0649(15) Uani 1 1 d . . . H19A H 0.3937 0.4628 0.3886 0.078 Uiso 1 1 calc R . . H19B H 0.5114 0.4470 0.3090 0.078 Uiso 1 1 calc R . . C21 C 0.3024(8) 0.3815(2) 0.1697(6) 0.0806(18) Uani 1 1 d . . . H21A H 0.3114 0.3465 0.1859 0.097 Uiso 1 1 calc R . . H21B H 0.4096 0.3917 0.1540 0.097 Uiso 1 1 calc R . . C20 C 0.2894(8) 0.4066(2) 0.2772(5) 0.0852(18) Uani 1 1 d . . . H20A H 0.3264 0.3840 0.3428 0.102 Uiso 1 1 calc R . . H20B H 0.1687 0.4142 0.2686 0.102 Uiso 1 1 calc R . . H3A H 1.064(8) 0.513(2) 0.655(6) 0.102 Uiso 1 1 d . . . H3B H 1.184(8) 0.493(2) 0.749(6) 0.102 Uiso 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 O3 0.084(3) 0.082(3) 0.038(2) 0.0074(18) 0.0149(18) -0.0119(19) S1 0.0376(6) 0.0516(7) 0.0424(7) 0.0055(6) 0.0173(5) -0.0009(5) O2 0.0551(19) 0.071(2) 0.0424(19) 0.0024(16) 0.0277(16) -0.0056(16) N2 0.048(2) 0.042(2) 0.047(2) -0.0008(18) 0.0200(19) -0.0053(17) C15 0.041(2) 0.045(3) 0.036(2) -0.001(2) 0.016(2) -0.002(2) N3 0.052(2) 0.051(3) 0.039(2) 0.001(2) 0.008(2) -0.0101(19) O1 0.0367(16) 0.069(2) 0.078(2) 0.0136(19) 0.0175(17) 0.0061(16) N1 0.049(2) 0.045(2) 0.061(3) -0.010(2) 0.022(2) -0.0079(18) C12 0.042(2) 0.039(3) 0.042(3) -0.002(2) 0.021(2) -0.0032(19) C14 0.034(2) 0.060(3) 0.046(3) 0.013(2) 0.011(2) 0.005(2) C13 0.053(3) 0.048(3) 0.048(3) 0.018(2) 0.019(2) 0.008(2) C16 0.044(2) 0.049(3) 0.039(3) 0.012(2) 0.013(2) -0.002(2) C3 0.055(3) 0.037(3) 0.057(3) 0.005(2) 0.030(2) 0.000(2) C5 0.052(3) 0.047(3) 0.053(3) 0.012(2) 0.028(2) 0.002(2) C17 0.040(2) 0.051(3) 0.046(3) 0.009(2) 0.008(2) -0.003(2) C10 0.072(3) 0.045(3) 0.052(3) 0.006(2) 0.023(3) 0.001(2) C9 0.067(3) 0.055(3) 0.056(3) 0.002(3) 0.020(3) 0.001(3) C8 0.045(3) 0.074(4) 0.053(3) 0.004(3) 0.017(2) 0.002(3) C2 0.061(3) 0.052(3) 0.073(4) 0.003(3) 0.032(3) -0.012(2) C1 0.052(3) 0.043(3) 0.072(4) -0.012(3) 0.025(3) -0.010(2) C6 0.082(4) 0.047(3) 0.074(4) 0.012(3) 0.028(3) 0.001(3) C7 0.076(4) 0.078(4) 0.061(4) 0.028(3) 0.023(3) 0.015(3) C11 0.075(4) 0.116(5) 0.062(4) 0.010(4) 0.006(3) 0.005(4) F2 0.201(5) 0.098(4) 0.151(5) -0.035(3) -0.033(4) -0.042(3) F3 0.126(4) 0.159(5) 0.125(4) -0.005(3) -0.020(3) -0.041(3) C4 0.085(4) 0.105(6) 0.080(5) -0.036(4) 0.038(4) -0.061(4) F1 0.099(3) 0.611(15) 0.227(7) -0.283(9) 0.093(4) -0.180(6) N4 0.062(2) 0.054(3) 0.043(2) -0.001(2) 0.015(2) -0.012(2) C24 0.056(3) 0.044(3) 0.042(3) 0.007(2) 0.007(2) 0.009(2) C23 0.045(3) 0.061(3) 0.058(3) 0.001(3) 0.003(2) 0.004(2) C22 0.066(3) 0.055(3) 0.068(4) 0.000(3) 0.020(3) -0.004(3) C18 0.073(3) 0.063(3) 0.048(3) -0.008(3) 0.023(3) -0.004(3) C19 0.065(3) 0.091(4) 0.039(3) 0.003(3) 0.015(2) -0.021(3) C21 0.095(4) 0.056(4) 0.088(5) 0.011(3) 0.020(4) 0.005(3) C20 0.098(4) 0.094(5) 0.063(4) 0.020(4) 0.021(4) -0.011(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O3 C24 1.244(5) . ? S1 O1 1.418(3) . ? S1 O2 1.429(3) . ? S1 N3 1.601(4) . ? S1 C15 1.779(4) . ? N2 N1 1.348(5) . ? N2 C3 1.372(5) . ? N2 C12 1.439(5) . ? C15 C14 1.361(6) . ? C15 C16 1.392(6) . ? N3 H3A 0.96(7) . ? N3 H3B 0.80(7) . ? N1 C1 1.346(5) . ? C12 C13 1.371(6) . ? C12 C17 1.385(6) . ? C14 C13 1.400(6) . ? C14 H14 0.9300 . ? C13 H13 0.9300 . ? C16 C17 1.378(5) . ? C16 H16 0.9300 . ? C3 C2 1.364(6) . ? C3 C5 1.472(7) . ? C5 C6 1.383(7) . ? C5 C10 1.385(6) . ? C17 H17 0.9300 . ? C10 C9 1.373(7) . ? C10 H10 0.9300 . ? C9 C8 1.392(7) . ? C9 H9 0.9300 . ? C8 C7 1.391(7) . ? C8 C11 1.511(7) . ? C2 C1 1.401(7) . ? C2 H2 0.9300 . ? C1 C4 1.456(8) . ? C6 C7 1.392(8) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? F2 C4 1.348(8) . ? F3 C4 1.318(7) . ? C4 F1 1.171(6) . ? N4 C24 1.311(6) . ? N4 C18 1.469(6) . ? N4 H4A 0.8600 . ? C24 C23 1.501(6) . ? C23 C22 1.530(7) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C22 C21 1.545(8) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C18 C19 1.509(7) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.519(8) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C21 C20 1.469(8) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C20 H20A 0.9700 . ? C20 H20B 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 O1 S1 O2 119.58(19) . . ? O1 S1 N3 107.7(2) . . ? O2 S1 N3 106.1(2) . . ? O1 S1 C15 108.0(2) . . ? O2 S1 C15 107.3(2) . . ? N3 S1 C15 107.61(19) . . ? N1 N2 C3 113.6(3) . . ? N1 N2 C12 117.2(3) . . ? C3 N2 C12 129.2(4) . . ? C14 C15 C16 120.5(4) . . ? C14 C15 S1 120.6(3) . . ? C16 C15 S1 118.9(3) . . ? S1 N3 H3A 119(4) . . ? S1 N3 H3B 121(5) . . ? H3A N3 H3B 103(6) . . ? C1 N1 N2 103.3(4) . . ? C13 C12 C17 121.5(4) . . ? C13 C12 N2 121.5(4) . . ? C17 C12 N2 116.8(4) . . ? C15 C14 C13 119.8(4) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C12 C13 C14 119.2(4) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C17 C16 C15 120.2(4) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C2 C3 N2 105.3(4) . . ? C2 C3 C5 129.1(4) . . ? N2 C3 C5 125.2(4) . . ? C6 C5 C10 117.8(5) . . ? C6 C5 C3 120.7(5) . . ? C10 C5 C3 121.2(4) . . ? C16 C17 C12 118.8(4) . . ? C16 C17 H17 120.6 . . ? C12 C17 H17 120.6 . . ? C9 C10 C5 121.5(5) . . ? C9 C10 H10 119.2 . . ? C5 C10 H10 119.2 . . ? C10 C9 C8 121.4(5) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C7 C8 C9 117.1(5) . . ? C7 C8 C11 121.7(5) . . ? C9 C8 C11 121.1(5) . . ? C3 C2 C1 106.0(4) . . ? C3 C2 H2 127.0 . . ? C1 C2 H2 127.0 . . ? N1 C1 C2 111.8(4) . . ? N1 C1 C4 118.9(5) . . ? C2 C1 C4 129.3(5) . . ? C5 C6 C7 120.9(5) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C8 C7 C6 121.2(5) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? F1 C4 F3 112.3(8) . . ? F1 C4 F2 105.9(7) . . ? F3 C4 F2 90.9(5) . . ? F1 C4 C1 116.3(6) . . ? F3 C4 C1 117.0(5) . . ? F2 C4 C1 110.9(6) . . ? C24 N4 C18 128.6(4) . . ? C24 N4 H4A 115.7 . . ? C18 N4 H4A 115.7 . . ? O3 C24 N4 120.9(4) . . ? O3 C24 C23 120.1(5) . . ? N4 C24 C23 119.0(4) . . ? C24 C23 C22 111.6(4) . . ? C24 C23 H23A 109.3 . . ? C22 C23 H23A 109.3 . . ? C24 C23 H23B 109.3 . . ? C22 C23 H23B 109.3 . . ? H23A C23 H23B 108.0 . . ? C23 C22 C21 114.8(4) . . ? C23 C22 H22A 108.6 . . ? C21 C22 H22A 108.6 . . ? C23 C22 H22B 108.6 . . ? C21 C22 H22B 108.6 . . ? H22A C22 H22B 107.5 . . ? N4 C18 C19 115.8(4) . . ? N4 C18 H18A 108.3 . . ? C19 C18 H18A 108.3 . . ? N4 C18 H18B 108.3 . . ? C19 C18 H18B 108.3 . . ? H18A C18 H18B 107.4 . . ? C18 C19 C20 116.2(5) . . ? C18 C19 H19A 108.2 . . ? C20 C19 H19A 108.2 . . ? C18 C19 H19B 108.2 . . ? C20 C19 H19B 108.2 . . ? H19A C19 H19B 107.4 . . ? C20 C21 C22 117.5(5) . . ? C20 C21 H21A 107.9 . . ? C22 C21 H21A 107.9 . . ? C20 C21 H21B 107.9 . . ? C22 C21 H21B 107.9 . . ? H21A C21 H21B 107.2 . . ? C21 C20 C19 116.3(5) . . ? C21 C20 H20A 108.2 . . ? C19 C20 H20A 108.2 . . ? C21 C20 H20B 108.2 . . ? C19 C20 H20B 108.2 . . ? H20A C20 H20B 107.4 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.917 _refine_diff_density_min -0.510 _refine_diff_density_rms 0.066 _database_code_depnum_ccdc_archive 'CCDC 954141' ####################################################################### # # 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_CEL-CPR _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Celecoxib-Caprolactam _chemical_melting_point 383 _chemical_formula_moiety 'C17 H14 F3 N3 O2 S, C6 H11 N O' _chemical_formula_sum 'C23 H25 F3 N4 O3 S' _chemical_formula_weight 494.53 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 monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.7189(11) _cell_length_b 8.7409(6) _cell_length_c 12.0503(10) _cell_angle_alpha 90.00 _cell_angle_beta 103.353(10) _cell_angle_gamma 90.00 _cell_volume 1200.98(17) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1827 _cell_measurement_theta_min 2.7590 _cell_measurement_theta_max 26.3066 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 0.190 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.30584 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; sadabs ; _diffrn_ambient_temperature 298(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 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4400 _diffrn_reflns_av_R_equivalents 0.0171 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 24.71 _reflns_number_total 2941 _reflns_number_gt 2685 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0927P)^2^+0.7840P] 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 mixed _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 -0.22(14) _refine_ls_number_reflns 2941 _refine_ls_number_parameters 316 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0595 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1559 _refine_ls_wR_factor_gt 0.1495 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 0.64277(8) 1.00846(13) 0.96227(8) 0.0417(3) Uani 1 1 d . . . C15 C 0.6019(3) 1.0001(6) 0.8111(3) 0.0415(9) Uani 1 1 d . . . N2 N 0.4964(4) 0.9879(6) 0.4553(3) 0.0548(10) Uani 1 1 d . . . N1 N 0.3825(4) 1.0129(6) 0.4112(3) 0.0575(10) Uani 1 1 d . . . O2 O 0.6194(3) 0.8608(4) 1.0014(3) 0.0579(9) Uani 1 1 d . . . C12 C 0.5353(4) 0.9921(7) 0.5779(4) 0.0535(12) Uani 1 1 d . . . C10 C 0.7546(5) 1.0180(8) 0.3351(5) 0.0722(16) Uani 1 1 d . . . H10 H 0.7207 1.0891 0.2799 0.087 Uiso 1 1 calc R . . O1 O 0.7591(3) 1.0680(4) 0.9931(3) 0.0555(9) Uani 1 1 d . . . C1 C 0.3718(5) 1.0151(7) 0.2995(4) 0.0601(12) Uani 1 1 d . . . N3 N 0.5594(4) 1.1265(6) 1.0049(4) 0.0514(11) Uani 1 1 d . . . C16 C 0.6574(4) 1.0912(6) 0.7471(4) 0.0523(12) Uani 1 1 d . . . H16 H 0.7178 1.1558 0.7831 0.063 Uiso 1 1 calc R . . C17 C 0.6240(5) 1.0873(7) 0.6295(4) 0.0593(13) Uani 1 1 d . . . H17 H 0.6615 1.1488 0.5860 0.071 Uiso 1 1 calc R . . C13 C 0.4799(5) 0.9016(7) 0.6414(4) 0.0596(14) Uani 1 1 d . . . H13 H 0.4195 0.8372 0.6053 0.072 Uiso 1 1 calc R . . C2 C 0.4791(5) 0.9906(7) 0.2713(4) 0.0606(13) Uani 1 1 d . . . H2 H 0.4934 0.9869 0.1986 0.073 Uiso 1 1 calc R . . C5 C 0.6858(5) 0.9426(7) 0.3966(4) 0.0582(13) Uani 1 1 d . . . C3 C 0.5596(5) 0.9730(6) 0.3733(4) 0.0548(13) Uani 1 1 d . . . C14 C 0.5129(4) 0.9053(6) 0.7584(4) 0.0515(12) Uani 1 1 d . . . H14 H 0.4749 0.8438 0.8016 0.062 Uiso 1 1 calc R . . C6 C 0.7394(5) 0.8368(8) 0.4782(5) 0.0681(16) Uani 1 1 d . . . H6 H 0.6949 0.7826 0.5196 0.082 Uiso 1 1 calc R . . C9 C 0.8721(6) 0.9886(9) 0.3550(5) 0.0773(17) Uani 1 1 d . . . H9 H 0.9164 1.0384 0.3111 0.093 Uiso 1 1 calc R . . C8 C 0.9268(5) 0.8881(8) 0.4376(5) 0.0702(16) Uani 1 1 d . . . C4 C 0.2573(6) 1.0492(8) 0.2248(4) 0.0707(18) Uani 1 1 d . . . C7 C 0.8580(6) 0.8123(7) 0.4977(5) 0.0722(17) Uani 1 1 d . . . H7 H 0.8929 0.7422 0.5533 0.087 Uiso 1 1 calc R . . F2 F 0.2584(5) 1.1473(9) 0.1497(5) 0.168(3) Uani 1 1 d . . . F3 F 0.1806(5) 1.0869(14) 0.2712(4) 0.238(6) Uani 1 1 d . . . F4 F 0.2125(6) 0.9358(7) 0.1625(7) 0.202(4) Uani 1 1 d . . . C11 C 1.0589(6) 0.8637(11) 0.4630(7) 0.102(2) Uani 1 1 d . . . H11A H 1.0758 0.7563 0.4715 0.152 Uiso 1 1 calc R . . H11B H 1.0951 0.9159 0.5323 0.152 Uiso 1 1 calc R . . H11C H 1.0891 0.9036 0.4013 0.152 Uiso 1 1 calc R . . O3 O 0.6515(3) 0.4478(5) 0.0571(4) 0.0723(11) Uani 1 1 d . . . C18 C 0.7517(4) 0.4659(7) 0.1141(4) 0.0557(14) Uani 1 1 d . . . N4 N 0.8286(4) 0.3489(6) 0.1262(5) 0.0794(16) Uani 1 1 d . . . H4A H 0.7993 0.2621 0.1006 0.095 Uiso 1 1 calc R . . C20 C 0.8874(6) 0.6890(9) 0.1351(7) 0.094(2) Uani 1 1 d . . . H20A H 0.8922 0.7913 0.1671 0.113 Uiso 1 1 calc R . . H20B H 0.8636 0.7001 0.0529 0.113 Uiso 1 1 calc R . . C19 C 0.7922(6) 0.6090(8) 0.1720(7) 0.087(2) Uani 1 1 d . . . H19A H 0.8181 0.5880 0.2530 0.105 Uiso 1 1 calc R . . H19B H 0.7258 0.6780 0.1621 0.105 Uiso 1 1 calc R . . C22 C 1.0237(6) 0.4624(9) 0.1356(9) 0.104(3) Uani 1 1 d . . . H22A H 1.0109 0.4525 0.0535 0.124 Uiso 1 1 calc R . . H22B H 1.1050 0.4363 0.1680 0.124 Uiso 1 1 calc R . . C23 C 0.9502(5) 0.3485(9) 0.1749(7) 0.088(2) Uani 1 1 d . . . H23A H 0.9801 0.2481 0.1624 0.105 Uiso 1 1 calc R . . H23B H 0.9609 0.3611 0.2567 0.105 Uiso 1 1 calc R . . C21 C 1.0070(6) 0.6256(10) 0.1618(9) 0.116(3) Uani 1 1 d . . . H21A H 1.0396 0.6406 0.2426 0.139 Uiso 1 1 calc R . . H21B H 1.0536 0.6864 0.1214 0.139 Uiso 1 1 calc R . . H3A H 0.476(5) 1.099(6) 0.987(4) 0.054(14) Uiso 1 1 d . . . H3B H 0.573(4) 1.215(7) 1.009(4) 0.042(15) Uiso 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 0.0392(5) 0.0421(6) 0.0431(5) -0.0008(5) 0.0079(4) 0.0010(5) C15 0.043(2) 0.041(2) 0.0418(19) -0.001(2) 0.0131(16) 0.007(2) N2 0.069(2) 0.056(3) 0.0427(18) 0.002(2) 0.0180(17) 0.001(2) N1 0.073(3) 0.057(2) 0.0439(19) 0.000(2) 0.0160(17) 0.006(3) O2 0.063(2) 0.051(2) 0.056(2) 0.0105(18) 0.0047(16) -0.0038(18) C12 0.065(3) 0.055(3) 0.043(2) -0.003(3) 0.016(2) 0.000(3) C10 0.095(4) 0.066(4) 0.061(3) 0.007(3) 0.030(3) -0.012(4) O1 0.0443(17) 0.062(2) 0.0589(18) -0.0083(17) 0.0084(14) -0.0051(16) C1 0.086(3) 0.047(3) 0.048(2) 0.005(3) 0.016(2) -0.001(3) N3 0.052(3) 0.051(3) 0.053(2) -0.009(2) 0.0162(19) -0.003(2) C16 0.052(3) 0.050(3) 0.056(3) 0.001(2) 0.014(2) -0.007(2) C17 0.067(3) 0.058(3) 0.056(3) 0.010(3) 0.021(2) -0.011(3) C13 0.066(3) 0.067(4) 0.046(3) -0.007(3) 0.013(2) -0.019(3) C2 0.089(3) 0.056(3) 0.039(2) 0.002(3) 0.020(2) -0.001(3) C5 0.084(4) 0.055(3) 0.042(2) 0.002(2) 0.027(2) -0.001(3) C3 0.080(3) 0.046(3) 0.045(2) 0.001(2) 0.027(2) 0.004(3) C14 0.062(3) 0.048(3) 0.050(3) -0.007(2) 0.025(2) -0.012(2) C6 0.086(4) 0.068(4) 0.059(3) 0.009(3) 0.033(3) -0.003(3) C9 0.089(4) 0.074(4) 0.080(3) 0.019(4) 0.044(3) 0.003(4) C8 0.078(4) 0.067(4) 0.070(3) -0.007(3) 0.027(3) -0.002(3) C4 0.089(4) 0.090(5) 0.030(2) -0.001(3) 0.009(2) -0.001(4) C7 0.090(4) 0.069(4) 0.063(3) 0.013(3) 0.027(3) 0.012(3) F2 0.131(4) 0.192(7) 0.144(4) 0.101(5) -0.044(3) -0.044(4) F3 0.123(4) 0.506(18) 0.073(3) 0.001(5) -0.002(3) 0.132(7) F4 0.157(5) 0.102(4) 0.271(9) -0.041(5) -0.109(6) 0.019(4) C11 0.086(5) 0.112(6) 0.115(6) 0.018(5) 0.039(4) 0.018(5) O3 0.0423(18) 0.066(3) 0.107(3) 0.003(2) 0.0123(19) -0.0012(18) C18 0.044(2) 0.061(4) 0.063(3) 0.006(3) 0.014(2) -0.006(2) N4 0.059(3) 0.050(3) 0.120(4) 0.008(3) 0.002(3) -0.013(3) C20 0.082(5) 0.059(4) 0.128(6) -0.001(4) -0.001(4) -0.013(4) C19 0.075(4) 0.066(4) 0.120(6) -0.020(4) 0.022(4) 0.010(4) C22 0.056(3) 0.082(6) 0.173(8) 0.000(5) 0.027(4) -0.008(4) C23 0.063(4) 0.060(4) 0.131(6) 0.016(4) 0.005(4) 0.005(3) C21 0.064(4) 0.074(5) 0.196(9) -0.005(6) 0.002(5) -0.017(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.422(4) . ? S1 O1 1.426(3) . ? S1 N3 1.586(5) . ? S1 C15 1.775(4) . ? C15 C16 1.373(7) . ? C15 C14 1.368(7) . ? N2 N1 1.335(5) . ? N2 C3 1.372(6) . ? N2 C12 1.443(5) . ? N1 C1 1.323(6) . ? C12 C13 1.364(7) . ? C12 C17 1.364(7) . ? C10 C9 1.367(8) . ? C10 C5 1.381(7) . ? C10 H10 0.9300 . ? C1 C2 1.393(8) . ? C1 C4 1.464(8) . ? N3 H3A 0.98(6) . ? N3 H3B 0.79(6) . ? C16 C17 1.380(7) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C13 C14 1.374(7) . ? C13 H13 0.9300 . ? C2 C3 1.374(7) . ? C2 H2 0.9300 . ? C5 C6 1.390(8) . ? C5 C3 1.464(8) . ? C14 H14 0.9300 . ? C6 C7 1.372(8) . ? C6 H6 0.9300 . ? C9 C8 1.371(9) . ? C9 H9 0.9300 . ? C8 C7 1.371(8) . ? C8 C11 1.522(9) . ? C4 F3 1.209(8) . ? C4 F2 1.248(7) . ? C4 F4 1.280(8) . ? C7 H7 0.9300 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? O3 C18 1.226(6) . ? C18 N4 1.349(8) . ? C18 C19 1.457(9) . ? N4 C23 1.410(7) . ? N4 H4A 0.8600 . ? C20 C19 1.470(10) . ? C20 C21 1.471(10) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C22 C23 1.465(10) . ? C22 C21 1.484(12) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C21 H21A 0.9700 . ? C21 H21B 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 O2 S1 O1 119.4(2) . . ? O2 S1 N3 107.6(3) . . ? O1 S1 N3 107.5(3) . . ? O2 S1 C15 106.0(2) . . ? O1 S1 C15 107.3(2) . . ? N3 S1 C15 108.6(2) . . ? C16 C15 C14 120.0(4) . . ? C16 C15 S1 120.2(4) . . ? C14 C15 S1 119.8(3) . . ? N1 N2 C3 112.7(4) . . ? N1 N2 C12 117.0(3) . . ? C3 N2 C12 130.1(4) . . ? C1 N1 N2 105.0(4) . . ? C13 C12 C17 120.6(4) . . ? C13 C12 N2 118.7(5) . . ? C17 C12 N2 120.6(4) . . ? C9 C10 C5 120.4(6) . . ? C9 C10 H10 119.8 . . ? C5 C10 H10 119.8 . . ? N1 C1 C2 111.5(5) . . ? N1 C1 C4 119.2(5) . . ? C2 C1 C4 129.2(4) . . ? S1 N3 H3A 115(3) . . ? S1 N3 H3B 122(4) . . ? H3A N3 H3B 115(5) . . ? C15 C16 C17 120.2(5) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C12 C17 C16 119.3(5) . . ? C12 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C12 C13 C14 120.3(5) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C3 C2 C1 105.7(4) . . ? C3 C2 H2 127.1 . . ? C1 C2 H2 127.1 . . ? C10 C5 C6 118.2(6) . . ? C10 C5 C3 120.0(5) . . ? C6 C5 C3 121.8(5) . . ? N2 C3 C2 105.1(4) . . ? N2 C3 C5 124.7(4) . . ? C2 C3 C5 130.2(4) . . ? C15 C14 C13 119.6(4) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C7 C6 C5 119.9(5) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C10 C9 C8 122.0(6) . . ? C10 C9 H9 119.0 . . ? C8 C9 H9 119.0 . . ? C7 C8 C9 117.4(6) . . ? C7 C8 C11 121.3(6) . . ? C9 C8 C11 121.2(6) . . ? F3 C4 F2 106.4(8) . . ? F3 C4 F4 103.6(8) . . ? F2 C4 F4 100.3(6) . . ? F3 C4 C1 116.4(4) . . ? F2 C4 C1 115.1(6) . . ? F4 C4 C1 113.3(6) . . ? C6 C7 C8 122.0(6) . . ? C6 C7 H7 119.0 . . ? C8 C7 H7 119.0 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O3 C18 N4 119.5(5) . . ? O3 C18 C19 122.9(6) . . ? N4 C18 C19 117.6(5) . . ? C18 N4 C23 129.2(6) . . ? C18 N4 H4A 115.4 . . ? C23 N4 H4A 115.4 . . ? C19 C20 C21 120.4(7) . . ? C19 C20 H20A 107.2 . . ? C21 C20 H20A 107.2 . . ? C19 C20 H20B 107.2 . . ? C21 C20 H20B 107.2 . . ? H20A C20 H20B 106.9 . . ? C18 C19 C20 116.7(6) . . ? C18 C19 H19A 108.1 . . ? C20 C19 H19A 108.1 . . ? C18 C19 H19B 108.1 . . ? C20 C19 H19B 108.1 . . ? H19A C19 H19B 107.3 . . ? C23 C22 C21 117.9(7) . . ? C23 C22 H22A 107.8 . . ? C21 C22 H22A 107.8 . . ? C23 C22 H22B 107.8 . . ? C21 C22 H22B 107.8 . . ? H22A C22 H22B 107.2 . . ? N4 C23 C22 118.5(6) . . ? N4 C23 H23A 107.7 . . ? C22 C23 H23A 107.7 . . ? N4 C23 H23B 107.7 . . ? C22 C23 H23B 107.7 . . ? H23A C23 H23B 107.1 . . ? C20 C21 C22 118.8(6) . . ? C20 C21 H21A 107.6 . . ? C22 C21 H21A 107.6 . . ? C20 C21 H21B 107.6 . . ? C22 C21 H21B 107.6 . . ? H21A C21 H21B 107.1 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.545 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.049 _database_code_depnum_ccdc_archive 'CCDC 954142' ####################################################################### # # 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_CXB-VLM-I _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Celecoxib-Valerolactam-Form-I _chemical_melting_point 379 _chemical_formula_moiety 'C17 H14 F3 N3 O2 S, C5 H9 N O' _chemical_formula_sum 'C22 H23 F3 N4 O3 S' _chemical_formula_weight 480.50 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7346(6) _cell_length_b 11.2689(10) _cell_length_c 12.2391(9) _cell_angle_alpha 81.622(7) _cell_angle_beta 87.560(6) _cell_angle_gamma 73.363(7) _cell_volume 1141.94(16) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1561 _cell_measurement_theta_min 2.9516 _cell_measurement_theta_max 28.8810 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.397 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 0.198 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.94105 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8078 _diffrn_reflns_av_R_equivalents 0.0424 _diffrn_reflns_av_sigmaI/netI 0.1050 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 26.37 _reflns_number_total 4662 _reflns_number_gt 2382 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0375P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4662 _refine_ls_number_parameters 305 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1207 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.1374 _refine_ls_wR_factor_gt 0.1078 _refine_ls_goodness_of_fit_ref 0.953 _refine_ls_restrained_S_all 0.953 _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 0.37641(10) 1.38263(7) 0.11604(7) 0.0438(2) Uani 1 1 d . . . O2 O 0.3222(2) 1.45938(19) 0.01306(16) 0.0494(6) Uani 1 1 d . . . N2 N 0.8258(3) 0.9105(2) 0.0049(2) 0.0404(7) Uani 1 1 d . . . N1 N 0.8768(3) 0.9147(2) -0.1019(2) 0.0445(7) Uani 1 1 d . . . O1 O 0.2627(3) 1.3539(2) 0.19420(18) 0.0588(7) Uani 1 1 d . . . C15 C 0.5057(4) 1.2406(3) 0.0833(2) 0.0377(7) Uani 1 1 d . . . C1 C 0.9650(4) 0.7997(3) -0.1086(3) 0.0416(8) Uani 1 1 d . . . C12 C 0.7165(4) 1.0215(3) 0.0343(2) 0.0373(7) Uani 1 1 d . . . C14 C 0.6233(4) 1.2440(3) 0.0040(2) 0.0443(8) Uani 1 1 d . . . H14 H 0.6306 1.3203 -0.0331 0.053 Uiso 1 1 calc R . . F3 F 0.9519(3) 0.8150(2) -0.29977(17) 0.0903(8) Uani 1 1 d . . . F1 F 1.1090(3) 0.6523(2) -0.21603(18) 0.0965(8) Uani 1 1 d . . . C13 C 0.7285(4) 1.1348(3) -0.0198(2) 0.0421(8) Uani 1 1 d . . . H13 H 0.8081 1.1370 -0.0723 0.050 Uiso 1 1 calc R . . C3 C 0.8826(4) 0.7938(3) 0.0636(3) 0.0411(8) Uani 1 1 d . . . N3 N 0.4802(4) 1.4514(3) 0.1742(2) 0.0497(8) Uani 1 1 d . . . H3A H 0.546(4) 1.476(3) 0.134(3) 0.060 Uiso 1 1 d . . . H3B H 0.516(4) 1.415(3) 0.244(3) 0.060 Uiso 1 1 d . . . C16 C 0.4930(4) 1.1278(3) 0.1362(2) 0.0438(8) Uani 1 1 d . . . H16 H 0.4140 1.1257 0.1892 0.053 Uiso 1 1 calc R . . C17 C 0.5966(4) 1.0177(3) 0.1113(3) 0.0432(8) Uani 1 1 d . . . H17 H 0.5861 0.9413 0.1459 0.052 Uiso 1 1 calc R . . C5 C 0.8609(4) 0.7604(3) 0.1826(3) 0.0412(8) Uani 1 1 d . . . C2 C 0.9725(4) 0.7202(3) -0.0087(3) 0.0466(8) Uani 1 1 d . . . H2 H 1.0270 0.6356 0.0055 0.056 Uiso 1 1 calc R . . F2 F 1.1646(3) 0.8245(3) -0.23350(19) 0.1002(9) Uani 1 1 d . . . C6 C 0.8892(4) 0.8311(3) 0.2593(3) 0.0531(9) Uani 1 1 d . . . H6 H 0.9160 0.9049 0.2357 0.064 Uiso 1 1 calc R . . C10 C 0.8205(4) 0.6522(3) 0.2207(3) 0.0543(10) Uani 1 1 d . . . H10 H 0.8006 0.6039 0.1705 0.065 Uiso 1 1 calc R . . C4 C 1.0460(5) 0.7718(3) -0.2131(3) 0.0549(9) Uani 1 1 d . . . C8 C 0.8380(4) 0.6834(4) 0.4093(3) 0.0566(10) Uani 1 1 d . . . C7 C 0.8775(4) 0.7917(4) 0.3702(3) 0.0607(10) Uani 1 1 d . . . H7 H 0.8970 0.8399 0.4206 0.073 Uiso 1 1 calc R . . C9 C 0.8092(4) 0.6146(3) 0.3319(3) 0.0602(10) Uani 1 1 d . . . H9 H 0.7815 0.5412 0.3556 0.072 Uiso 1 1 calc R . . C11 C 0.8308(5) 0.6396(4) 0.5313(3) 0.0872(14) Uani 1 1 d . . . H1A H 0.9349 0.6221 0.5631 0.131 Uiso 1 1 calc R . . H1B H 0.7964 0.5651 0.5425 0.131 Uiso 1 1 calc R . . H1C H 0.7566 0.7038 0.5661 0.131 Uiso 1 1 calc R . . N4 N 0.4017(4) 0.6588(3) 0.4193(2) 0.0694(10) Uani 1 1 d . . . H4A H 0.4247 0.5803 0.4143 0.083 Uiso 1 1 calc R . . O3 O 0.4433(3) 0.6063(2) 0.59966(19) 0.0771(9) Uani 1 1 d . . . C22 C 0.3613(5) 0.7447(4) 0.3170(3) 0.0796(13) Uani 1 1 d . . . H22A H 0.4507 0.7272 0.2663 0.096 Uiso 1 1 calc R . . H22B H 0.2705 0.7310 0.2832 0.096 Uiso 1 1 calc R . . C19 C 0.3718(6) 0.8235(4) 0.5311(3) 0.0835(13) Uani 1 1 d . . . H19A H 0.2776 0.8460 0.5770 0.100 Uiso 1 1 calc R . . H19B H 0.4603 0.8347 0.5697 0.100 Uiso 1 1 calc R . . C20 C 0.3451(9) 0.9107(5) 0.4269(4) 0.172(3) Uani 1 1 d . . . H20A H 0.2526 0.9800 0.4379 0.207 Uiso 1 1 calc R . . H20B H 0.4361 0.9443 0.4162 0.207 Uiso 1 1 calc R . . C21 C 0.3233(8) 0.8734(5) 0.3344(4) 0.134(2) Uani 1 1 d . . . H21A H 0.3816 0.9132 0.2785 0.160 Uiso 1 1 calc R . . H21B H 0.2109 0.9097 0.3167 0.160 Uiso 1 1 calc R . . C18 C 0.4067(5) 0.6892(4) 0.5189(3) 0.0611(10) 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 0.0506(5) 0.0364(5) 0.0406(5) -0.0071(4) 0.0031(4) -0.0059(4) O2 0.0589(15) 0.0407(14) 0.0408(13) -0.0008(10) -0.0087(11) -0.0027(11) N2 0.0479(16) 0.0305(16) 0.0398(16) -0.0043(12) 0.0019(13) -0.0070(13) N1 0.0525(17) 0.0372(17) 0.0403(17) -0.0089(13) 0.0052(14) -0.0064(14) O1 0.0576(15) 0.0539(16) 0.0622(16) -0.0107(12) 0.0226(13) -0.0136(13) C15 0.0446(19) 0.0329(19) 0.0346(18) -0.0051(14) 0.0026(15) -0.0092(15) C1 0.046(2) 0.035(2) 0.044(2) -0.0110(16) 0.0043(16) -0.0097(16) C12 0.0444(19) 0.0277(18) 0.0389(18) -0.0050(14) -0.0025(16) -0.0083(15) C14 0.058(2) 0.0275(19) 0.043(2) 0.0001(14) 0.0065(17) -0.0094(17) F3 0.1008(19) 0.106(2) 0.0493(14) -0.0189(13) -0.0043(13) -0.0011(16) F1 0.134(2) 0.0532(15) 0.0852(17) -0.0248(13) 0.0396(15) 0.0034(15) C13 0.050(2) 0.035(2) 0.0395(19) -0.0044(15) 0.0104(15) -0.0106(16) C3 0.044(2) 0.0285(19) 0.049(2) -0.0057(15) -0.0035(17) -0.0073(16) N3 0.071(2) 0.0413(18) 0.0357(18) -0.0043(14) -0.0027(15) -0.0148(16) C16 0.046(2) 0.040(2) 0.043(2) -0.0009(16) 0.0054(16) -0.0118(17) C17 0.047(2) 0.032(2) 0.047(2) 0.0025(15) 0.0042(17) -0.0108(16) C5 0.0420(19) 0.0358(19) 0.043(2) -0.0047(15) -0.0015(16) -0.0059(16) C2 0.053(2) 0.035(2) 0.051(2) -0.0099(16) 0.0016(17) -0.0084(17) F2 0.111(2) 0.142(2) 0.0791(17) -0.0491(16) 0.0466(14) -0.075(2) C6 0.067(2) 0.043(2) 0.053(2) -0.0108(17) -0.003(2) -0.0191(19) C10 0.078(3) 0.041(2) 0.045(2) -0.0026(16) -0.0081(19) -0.020(2) C4 0.065(3) 0.045(2) 0.052(2) -0.0095(18) 0.009(2) -0.012(2) C8 0.053(2) 0.066(3) 0.044(2) -0.0051(19) -0.0020(18) -0.008(2) C7 0.069(3) 0.066(3) 0.051(2) -0.020(2) -0.007(2) -0.018(2) C9 0.074(3) 0.050(2) 0.054(2) 0.0029(18) -0.003(2) -0.018(2) C11 0.102(3) 0.108(4) 0.045(2) -0.003(2) -0.002(2) -0.022(3) N4 0.104(3) 0.059(2) 0.0416(19) 0.0008(16) -0.0086(18) -0.020(2) O3 0.123(2) 0.0647(19) 0.0399(15) 0.0063(13) -0.0080(16) -0.0257(18) C22 0.104(3) 0.076(3) 0.043(2) 0.011(2) -0.008(2) -0.009(3) C19 0.111(4) 0.069(3) 0.068(3) -0.014(2) 0.008(3) -0.020(3) C20 0.344(10) 0.057(4) 0.085(4) 0.006(3) -0.035(5) -0.010(5) C21 0.248(7) 0.072(4) 0.068(4) 0.016(3) -0.033(4) -0.033(4) C18 0.074(3) 0.063(3) 0.043(2) -0.004(2) 0.003(2) -0.018(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.421(2) . ? S1 O2 1.4350(19) . ? S1 N3 1.596(3) . ? S1 C15 1.764(3) . ? N2 N1 1.361(3) . ? N2 C3 1.369(4) . ? N2 C12 1.422(4) . ? N1 C1 1.317(4) . ? C15 C16 1.372(4) . ? C15 C14 1.387(4) . ? C1 C2 1.398(4) . ? C1 C4 1.466(5) . ? C12 C13 1.380(4) . ? C12 C17 1.384(4) . ? C14 C13 1.371(4) . ? C14 H14 0.9300 . ? F3 C4 1.317(4) . ? F1 C4 1.306(4) . ? C13 H13 0.9300 . ? C3 C2 1.367(4) . ? C3 C5 1.468(4) . ? N3 H3A 0.82(3) . ? N3 H3B 0.92(3) . ? C16 C17 1.377(4) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C5 C10 1.377(4) . ? C5 C6 1.389(4) . ? C2 H2 0.9300 . ? F2 C4 1.332(4) . ? C6 C7 1.374(4) . ? C6 H6 0.9300 . ? C10 C9 1.373(4) . ? C10 H10 0.9300 . ? C8 C7 1.376(5) . ? C8 C9 1.382(4) . ? C8 C11 1.508(4) . ? C7 H7 0.9300 . ? C9 H9 0.9300 . ? C11 H1A 0.9600 . ? C11 H1B 0.9600 . ? C11 H1C 0.9600 . ? N4 C18 1.319(4) . ? N4 C22 1.455(4) . ? N4 H4A 0.8600 . ? O3 C18 1.241(4) . ? C22 C21 1.438(5) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C19 C20 1.475(5) . ? C19 C18 1.485(5) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.302(6) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9700 . ? C21 H21B 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 O1 S1 O2 119.49(14) . . ? O1 S1 N3 107.82(15) . . ? O2 S1 N3 106.53(13) . . ? O1 S1 C15 108.08(14) . . ? O2 S1 C15 106.67(14) . . ? N3 S1 C15 107.76(15) . . ? N1 N2 C3 112.0(3) . . ? N1 N2 C12 116.6(2) . . ? C3 N2 C12 131.2(3) . . ? C1 N1 N2 104.1(2) . . ? C16 C15 C14 119.9(3) . . ? C16 C15 S1 121.0(3) . . ? C14 C15 S1 119.1(2) . . ? N1 C1 C2 112.6(3) . . ? N1 C1 C4 118.7(3) . . ? C2 C1 C4 128.6(3) . . ? C13 C12 C17 120.1(3) . . ? C13 C12 N2 118.0(3) . . ? C17 C12 N2 121.8(3) . . ? C13 C14 C15 120.0(3) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C13 C12 120.0(3) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C2 C3 N2 106.1(3) . . ? C2 C3 C5 128.0(3) . . ? N2 C3 C5 125.7(3) . . ? S1 N3 H3A 115(2) . . ? S1 N3 H3B 115.7(19) . . ? H3A N3 H3B 115(3) . . ? C15 C16 C17 120.4(3) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C16 C17 C12 119.5(3) . . ? C16 C17 H17 120.2 . . ? C12 C17 H17 120.2 . . ? C10 C5 C6 118.4(3) . . ? C10 C5 C3 119.7(3) . . ? C6 C5 C3 121.8(3) . . ? C3 C2 C1 105.1(3) . . ? C3 C2 H2 127.4 . . ? C1 C2 H2 127.4 . . ? C7 C6 C5 119.7(3) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C9 C10 C5 120.9(3) . . ? C9 C10 H10 119.5 . . ? C5 C10 H10 119.5 . . ? F1 C4 F3 106.7(3) . . ? F1 C4 F2 106.3(3) . . ? F3 C4 F2 104.5(3) . . ? F1 C4 C1 113.3(3) . . ? F3 C4 C1 113.4(3) . . ? F2 C4 C1 112.0(3) . . ? C7 C8 C9 117.1(3) . . ? C7 C8 C11 121.6(3) . . ? C9 C8 C11 121.3(3) . . ? C6 C7 C8 122.4(3) . . ? C6 C7 H7 118.8 . . ? C8 C7 H7 118.8 . . ? C10 C9 C8 121.4(3) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C8 C11 H1A 109.5 . . ? C8 C11 H1B 109.5 . . ? H1A C11 H1B 109.5 . . ? C8 C11 H1C 109.5 . . ? H1A C11 H1C 109.5 . . ? H1B C11 H1C 109.5 . . ? C18 N4 C22 126.6(3) . . ? C18 N4 H4A 116.7 . . ? C22 N4 H4A 116.7 . . ? C21 C22 N4 112.3(3) . . ? C21 C22 H22A 109.1 . . ? N4 C22 H22A 109.1 . . ? C21 C22 H22B 109.1 . . ? N4 C22 H22B 109.1 . . ? H22A C22 H22B 107.9 . . ? C20 C19 C18 115.3(4) . . ? C20 C19 H19A 108.5 . . ? C18 C19 H19A 108.5 . . ? C20 C19 H19B 108.5 . . ? C18 C19 H19B 108.5 . . ? H19A C19 H19B 107.5 . . ? C21 C20 C19 120.9(5) . . ? C21 C20 H20A 107.1 . . ? C19 C20 H20A 107.1 . . ? C21 C20 H20B 107.1 . . ? C19 C20 H20B 107.1 . . ? H20A C20 H20B 106.8 . . ? C20 C21 C22 124.7(4) . . ? C20 C21 H21A 106.2 . . ? C22 C21 H21A 106.2 . . ? C20 C21 H21B 106.2 . . ? C22 C21 H21B 106.2 . . ? H21A C21 H21B 106.4 . . ? O3 C18 N4 120.1(4) . . ? O3 C18 C19 121.3(3) . . ? N4 C18 C19 118.6(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.318 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.047 _database_code_depnum_ccdc_archive 'CCDC 954143' ####################################################################### # # 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_CEL-VLM-II _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Celecoxib-Valerolactam-Form-II _chemical_melting_point 381 _chemical_formula_moiety 'C17 H14 F3 N3 O2 S, C5 H9 N O' _chemical_formula_sum 'C22 H23 F3 N4 O3 S' _chemical_formula_weight 480.50 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 22.591(2) _cell_length_b 8.6211(8) _cell_length_c 23.814(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.1630(10) _cell_angle_gamma 90.00 _cell_volume 4533.9(7) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5438 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 27.38 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2000 _exptl_absorpt_coefficient_mu 0.199 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 41174 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0229 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 24.71 _reflns_number_total 7737 _reflns_number_gt 6018 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.1081P)^2^+2.9650P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7737 _refine_ls_number_parameters 621 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0762 _refine_ls_R_factor_gt 0.0618 _refine_ls_wR_factor_ref 0.1878 _refine_ls_wR_factor_gt 0.1728 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 H7A H 0.5186(16) 0.869(4) 0.5227(15) 0.067(11) Uiso 1 1 d . . . S1 S 0.19211(4) 0.68717(8) 0.02149(3) 0.0471(2) Uani 1 1 d . . . N5 N 0.24991(10) 0.7291(3) 0.27684(9) 0.0450(6) Uani 1 1 d . . . C15 C 0.20960(12) 0.7031(3) 0.09779(11) 0.0404(6) Uani 1 1 d . . . C3 C 0.21443(13) 0.7125(3) 0.31678(11) 0.0436(6) Uani 1 1 d . . . C14 C 0.25769(13) 0.6227(4) 0.12883(12) 0.0518(7) Uani 1 1 d . . . H14 H 0.2818 0.5628 0.1101 0.062 Uiso 1 1 calc R . . C9 C 0.05255(14) 0.6808(4) 0.32896(13) 0.0534(8) Uani 1 1 d . . . H9 H 0.0278 0.7230 0.3516 0.064 Uiso 1 1 calc R . . C8 C 0.02873(14) 0.5733(4) 0.28761(13) 0.0524(7) Uani 1 1 d . . . O6 O 0.06660(11) -0.0266(3) 0.97252(11) 0.0690(7) Uani 1 1 d . . . C5 C 0.15033(12) 0.6657(3) 0.30446(11) 0.0430(6) Uani 1 1 d . . . C2 C 0.25215(13) 0.7404(4) 0.36891(12) 0.0485(7) Uani 1 1 d . . . H2 H 0.2422 0.7388 0.4048 0.058 Uiso 1 1 calc R . . N6 N 0.18279(16) 0.8547(3) -0.00537(11) 0.0532(7) Uani 1 1 d . . . C16 C 0.17391(13) 0.7935(4) 0.12540(12) 0.0514(7) Uani 1 1 d . . . H16 H 0.1414 0.8485 0.1042 0.062 Uiso 1 1 calc R . . N4 N 0.30809(11) 0.7645(3) 0.30118(10) 0.0495(6) Uani 1 1 d . . . C17 C 0.18678(14) 0.8016(4) 0.18433(12) 0.0522(7) Uani 1 1 d . . . H17 H 0.1631 0.8626 0.2031 0.063 Uiso 1 1 calc R . . C12 C 0.23453(12) 0.7199(3) 0.21538(11) 0.0419(6) Uani 1 1 d . . . C7 C 0.06713(14) 0.5108(4) 0.25519(13) 0.0571(8) Uani 1 1 d . . . H7 H 0.0522 0.4372 0.2272 0.069 Uiso 1 1 calc R . . O2 O 0.13563(12) 0.6095(3) 0.00541(10) 0.0758(7) Uani 1 1 d . . . C13 C 0.27049(14) 0.6306(4) 0.18803(12) 0.0547(8) Uani 1 1 d . . . H13 H 0.3031 0.5760 0.2093 0.066 Uiso 1 1 calc R . . C40 C 0.05479(13) 0.1022(4) 0.94954(13) 0.0504(7) Uani 1 1 d . . . C10 C 0.11237(13) 0.7279(3) 0.33771(12) 0.0480(7) Uani 1 1 d . . . H10 H 0.1272 0.8011 0.3658 0.058 Uiso 1 1 calc R . . C1 C 0.30837(14) 0.7717(3) 0.35677(12) 0.0481(7) Uani 1 1 d . . . F2 F 0.35830(12) 0.8189(5) 0.44981(10) 0.1372(14) Uani 1 1 d . . . O1 O 0.24444(12) 0.6211(3) 0.00657(9) 0.0755(7) Uani 1 1 d . . . F3 F 0.40750(11) 0.7073(4) 0.39988(14) 0.1282(12) Uani 1 1 d . . . C6 C 0.12690(14) 0.5553(4) 0.26354(12) 0.0535(7) Uani 1 1 d . . . H6 H 0.1518 0.5108 0.2415 0.064 Uiso 1 1 calc R . . N8 N 0.00630(14) 0.1783(3) 0.95471(15) 0.0677(8) Uani 1 1 d . . . C41 C 0.09650(15) 0.1728(4) 0.91551(14) 0.0591(8) Uani 1 1 d . . . H41A H 0.1353 0.1909 0.9411 0.071 Uiso 1 1 calc R . . H41B H 0.1029 0.0979 0.8870 0.071 Uiso 1 1 calc R . . C4 C 0.36520(15) 0.8114(4) 0.39741(13) 0.0570(8) Uani 1 1 d . . . C11 C -0.03653(15) 0.5210(5) 0.27859(17) 0.0757(10) Uani 1 1 d . . . H11A H -0.0439 0.4782 0.3137 0.113 Uiso 1 1 calc R . . H11B H -0.0443 0.4435 0.2490 0.113 Uiso 1 1 calc R . . H11C H -0.0628 0.6081 0.2673 0.113 Uiso 1 1 calc R . . F1 F 0.38880(16) 0.9396(4) 0.38748(15) 0.1737(19) Uani 1 1 d . . . C43 C 0.0287(2) 0.4012(5) 0.9022(2) 0.1037(16) Uani 1 1 d . . . H43A H 0.0471 0.4863 0.9263 0.124 Uiso 1 1 calc R . . H43B H 0.0048 0.4472 0.8676 0.124 Uiso 1 1 calc R . . C44 C -0.0114(2) 0.3314(5) 0.9304(3) 0.117(2) Uani 1 1 d . . . H44A H -0.0501 0.3218 0.9038 0.141 Uiso 1 1 calc R . . H44B H -0.0172 0.3993 0.9613 0.141 Uiso 1 1 calc R . . C42 C 0.0759(2) 0.3205(6) 0.8857(3) 0.1094(18) Uani 1 1 d . . . H42A H 0.1105 0.3895 0.8906 0.131 Uiso 1 1 calc R . . H42B H 0.0636 0.2984 0.8449 0.131 Uiso 1 1 calc R . . S2 S 0.30537(4) 0.30907(9) 0.48281(3) 0.0486(2) Uani 1 1 d . . . N2 N 0.24965(10) 0.2129(3) 0.22999(9) 0.0434(5) Uani 1 1 d . . . C20 C 0.28525(12) 0.1976(3) 0.19032(11) 0.0411(6) Uani 1 1 d . . . C32 C 0.29100(12) 0.2736(3) 0.40768(11) 0.0420(6) Uani 1 1 d . . . C22 C 0.35154(12) 0.1770(3) 0.20345(11) 0.0423(6) Uani 1 1 d . . . N1 N 0.19020(10) 0.2300(3) 0.20516(9) 0.0470(6) Uani 1 1 d . . . C31 C 0.24586(13) 0.1720(4) 0.38328(11) 0.0513(7) Uani 1 1 d . . . H31 H 0.2240 0.1187 0.4062 0.062 Uiso 1 1 calc R . . C29 C 0.26588(12) 0.2310(3) 0.29099(11) 0.0413(6) Uani 1 1 d . . . F4 F 0.09451(10) 0.1254(3) 0.10506(11) 0.0983(8) Uani 1 1 d . . . O4 O 0.24897(12) 0.3552(3) 0.49494(9) 0.0738(7) Uani 1 1 d . . . C24 C 0.44339(14) 0.0681(4) 0.25794(13) 0.0552(8) Uani 1 1 d . . . H24 H 0.4628 0.0075 0.2886 0.066 Uiso 1 1 calc R . . N3 N 0.32384(15) 0.1512(3) 0.51607(10) 0.0504(6) Uani 1 1 d . . . C26 C 0.44716(13) 0.2259(4) 0.17727(12) 0.0493(7) Uani 1 1 d . . . H26 H 0.4689 0.2728 0.1528 0.059 Uiso 1 1 calc R . . C25 C 0.47757(13) 0.1378(4) 0.22279(12) 0.0494(7) Uani 1 1 d . . . F5 F 0.13824(10) 0.2700(4) 0.05602(9) 0.1060(9) Uani 1 1 d . . . C34 C 0.31079(14) 0.3315(4) 0.31560(12) 0.0515(7) Uani 1 1 d . . . H34 H 0.3325 0.3852 0.2927 0.062 Uiso 1 1 calc R . . C19 C 0.24617(13) 0.2055(3) 0.13768(11) 0.0465(7) Uani 1 1 d . . . H19 H 0.2559 0.1983 0.1017 0.056 Uiso 1 1 calc R . . C18 C 0.18917(13) 0.2264(3) 0.14953(11) 0.0443(6) Uani 1 1 d . . . C33 C 0.32399(14) 0.3533(3) 0.37438(12) 0.0501(7) Uani 1 1 d . . . H33 H 0.3547 0.4207 0.3913 0.060 Uiso 1 1 calc R . . C27 C 0.38519(13) 0.2458(3) 0.16745(12) 0.0472(7) Uani 1 1 d . . . H27 H 0.3658 0.3056 0.1365 0.057 Uiso 1 1 calc R . . C30 C 0.23330(13) 0.1498(4) 0.32445(11) 0.0501(7) Uani 1 1 d . . . H30 H 0.2031 0.0809 0.3075 0.060 Uiso 1 1 calc R . . C23 C 0.38165(13) 0.0862(4) 0.24863(12) 0.0524(7) Uani 1 1 d . . . H23 H 0.3600 0.0374 0.2727 0.063 Uiso 1 1 calc R . . C21 C 0.13074(14) 0.2472(4) 0.10829(12) 0.0539(8) Uani 1 1 d . . . O3 O 0.35602(13) 0.4109(3) 0.49606(9) 0.0767(7) Uani 1 1 d . . . C28 C 0.54523(14) 0.1143(5) 0.23303(15) 0.0690(9) Uani 1 1 d . . . H28A H 0.5597 0.1490 0.2000 0.103 Uiso 1 1 calc R . . H28B H 0.5544 0.0062 0.2394 0.103 Uiso 1 1 calc R . . H28C H 0.5646 0.1728 0.2661 0.103 Uiso 1 1 calc R . . F6 F 0.09940(12) 0.3642(4) 0.12088(12) 0.1281(12) Uani 1 1 d . . . N7 N 0.49418(15) 0.8256(4) 0.54150(16) 0.0740(9) Uani 1 1 d . . . C35 C 0.45307(14) 0.9091(4) 0.55832(14) 0.0549(8) Uani 1 1 d . . . C36 C 0.41561(19) 0.8374(5) 0.59510(18) 0.0783(11) Uani 1 1 d . . . H36A H 0.3735 0.8458 0.5755 0.094 Uiso 1 1 calc R . . H36B H 0.4206 0.8976 0.6302 0.094 Uiso 1 1 calc R . . C37 C 0.4283(3) 0.6716(5) 0.6111(2) 0.1069(17) Uani 1 1 d . . . H37A H 0.4377 0.6648 0.6527 0.128 Uiso 1 1 calc R . . H37B H 0.3914 0.6130 0.5976 0.128 Uiso 1 1 calc R . . O5 O 0.44406(11) 1.0473(3) 0.54269(12) 0.0765(7) Uani 1 1 d . . . C39 C 0.5064(3) 0.6632(5) 0.5564(3) 0.139(3) Uani 1 1 d . . . H39A H 0.4995 0.6038 0.5210 0.166 Uiso 1 1 calc R . . H39B H 0.5490 0.6535 0.5741 0.166 Uiso 1 1 calc R . . C38 C 0.4749(3) 0.5986(6) 0.5909(3) 0.129(2) Uani 1 1 d . . . H38A H 0.5042 0.5654 0.6246 0.155 Uiso 1 1 calc R . . H38B H 0.4575 0.5047 0.5718 0.155 Uiso 1 1 calc R . . H3A H 0.3618(15) 0.125(4) 0.5178(13) 0.050(9) Uiso 1 1 d . . . H3B H 0.2975(16) 0.082(4) 0.5107(15) 0.062(11) Uiso 1 1 d . . . H6B H 0.2128(16) 0.914(4) 0.0012(15) 0.064(11) Uiso 1 1 d . . . H6A H 0.1459(17) 0.887(4) -0.0112(16) 0.070(12) Uiso 1 1 d . . . H8A H -0.0149(14) 0.144(4) 0.9762(13) 0.048(9) Uiso 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 0.0661(5) 0.0438(4) 0.0315(4) 0.0006(3) 0.0100(3) 0.0032(3) N5 0.0463(13) 0.0560(14) 0.0330(11) -0.0011(10) 0.0089(10) -0.0040(11) C15 0.0482(15) 0.0412(14) 0.0332(13) 0.0018(11) 0.0117(11) 0.0006(12) C3 0.0539(16) 0.0450(15) 0.0349(14) -0.0025(12) 0.0162(12) 0.0012(13) C14 0.0560(17) 0.0656(19) 0.0374(15) 0.0051(14) 0.0179(13) 0.0171(15) C9 0.0555(18) 0.0568(19) 0.0536(17) -0.0033(14) 0.0242(14) 0.0074(14) C8 0.0555(17) 0.0517(17) 0.0511(17) 0.0012(14) 0.0135(14) -0.0011(14) O6 0.0707(15) 0.0573(14) 0.0837(17) 0.0225(12) 0.0269(12) 0.0117(12) C5 0.0507(16) 0.0449(15) 0.0351(14) -0.0010(11) 0.0129(12) 0.0000(12) C2 0.0582(18) 0.0538(17) 0.0351(14) -0.0044(12) 0.0135(13) -0.0027(14) N6 0.0575(18) 0.0537(16) 0.0468(15) 0.0114(12) 0.0076(13) -0.0024(15) C16 0.0557(17) 0.0574(18) 0.0394(15) 0.0004(13) 0.0063(13) 0.0190(14) N4 0.0507(14) 0.0598(15) 0.0383(13) -0.0001(11) 0.0099(11) -0.0055(12) C17 0.0580(18) 0.0564(18) 0.0442(16) -0.0056(13) 0.0154(14) 0.0161(14) C12 0.0444(15) 0.0498(16) 0.0329(13) -0.0010(12) 0.0112(11) -0.0042(12) C7 0.0624(19) 0.063(2) 0.0479(17) -0.0131(15) 0.0154(14) -0.0111(16) O2 0.0997(18) 0.0678(15) 0.0522(13) -0.0017(11) -0.0014(12) -0.0319(14) C13 0.0537(17) 0.073(2) 0.0386(15) 0.0089(14) 0.0126(13) 0.0177(15) C40 0.0532(17) 0.0474(17) 0.0482(16) 0.0027(14) 0.0051(13) -0.0012(14) C10 0.0595(18) 0.0463(16) 0.0402(15) -0.0065(12) 0.0149(13) 0.0002(14) C1 0.0587(18) 0.0480(16) 0.0367(15) -0.0036(12) 0.0082(13) -0.0009(14) F2 0.0874(17) 0.265(4) 0.0532(14) -0.0444(19) 0.0000(12) -0.018(2) O1 0.1042(18) 0.0863(17) 0.0416(12) 0.0067(12) 0.0283(12) 0.0414(15) F3 0.0692(15) 0.150(3) 0.145(3) -0.059(2) -0.0242(15) 0.0251(16) C6 0.0581(18) 0.0586(18) 0.0481(16) -0.0130(14) 0.0211(14) -0.0028(15) N8 0.0596(17) 0.0594(18) 0.090(2) 0.0264(16) 0.0301(16) 0.0082(14) C41 0.0609(19) 0.064(2) 0.0531(18) 0.0059(15) 0.0124(15) 0.0016(16) C4 0.0599(19) 0.066(2) 0.0427(17) -0.0030(14) 0.0046(14) -0.0029(17) C11 0.056(2) 0.088(3) 0.086(3) -0.012(2) 0.0222(18) -0.0085(19) F1 0.164(3) 0.142(3) 0.161(3) 0.067(2) -0.088(2) -0.101(2) C43 0.089(3) 0.078(3) 0.150(5) 0.054(3) 0.037(3) 0.019(2) C44 0.119(4) 0.080(3) 0.176(5) 0.064(3) 0.082(4) 0.041(3) C42 0.113(4) 0.086(3) 0.149(5) 0.056(3) 0.074(3) 0.021(3) S2 0.0669(5) 0.0485(4) 0.0304(4) -0.0061(3) 0.0105(3) 0.0038(3) N2 0.0446(13) 0.0560(14) 0.0300(11) 0.0010(10) 0.0084(10) 0.0038(11) C20 0.0490(15) 0.0446(15) 0.0311(13) 0.0022(11) 0.0118(11) 0.0017(12) C32 0.0530(16) 0.0449(15) 0.0287(13) -0.0019(11) 0.0098(11) 0.0053(13) C22 0.0492(15) 0.0465(16) 0.0327(13) -0.0007(11) 0.0120(11) 0.0000(12) N1 0.0473(13) 0.0583(15) 0.0354(12) -0.0007(11) 0.0089(10) 0.0063(11) C31 0.0565(17) 0.066(2) 0.0343(14) -0.0041(13) 0.0162(13) -0.0111(15) C29 0.0467(15) 0.0485(16) 0.0291(13) 0.0002(11) 0.0087(11) 0.0043(12) F4 0.0712(14) 0.1042(19) 0.1049(18) 0.0221(15) -0.0144(12) -0.0198(13) O4 0.0898(17) 0.0908(18) 0.0445(12) -0.0059(12) 0.0223(11) 0.0351(14) C24 0.0549(18) 0.062(2) 0.0484(17) 0.0116(15) 0.0094(14) 0.0057(15) N3 0.0542(17) 0.0584(17) 0.0376(13) 0.0019(11) 0.0073(12) 0.0002(14) C26 0.0557(17) 0.0526(17) 0.0436(15) 0.0012(13) 0.0192(13) -0.0074(14) C25 0.0493(16) 0.0521(17) 0.0481(16) -0.0051(13) 0.0132(13) -0.0024(13) F5 0.0805(15) 0.184(3) 0.0462(12) 0.0280(15) -0.0029(10) -0.0045(16) C34 0.0617(18) 0.0549(18) 0.0390(15) 0.0063(13) 0.0129(13) -0.0095(14) C19 0.0553(17) 0.0533(17) 0.0322(14) 0.0027(12) 0.0119(12) 0.0024(14) C18 0.0540(17) 0.0462(15) 0.0327(14) 0.0024(12) 0.0087(12) 0.0049(13) C33 0.0628(18) 0.0482(16) 0.0378(15) 0.0010(12) 0.0072(13) -0.0105(14) C27 0.0560(17) 0.0490(16) 0.0377(14) 0.0044(12) 0.0122(13) 0.0002(13) C30 0.0547(17) 0.0616(18) 0.0344(14) -0.0040(13) 0.0103(12) -0.0101(14) C23 0.0548(17) 0.0584(18) 0.0467(16) 0.0142(14) 0.0170(13) 0.0022(14) C21 0.0564(18) 0.064(2) 0.0395(16) 0.0042(14) 0.0066(14) 0.0041(16) O3 0.113(2) 0.0683(15) 0.0457(12) -0.0116(11) 0.0103(13) -0.0343(14) C28 0.0528(19) 0.086(3) 0.069(2) 0.0023(19) 0.0152(16) 0.0025(18) F6 0.112(2) 0.134(2) 0.112(2) -0.0390(18) -0.0352(16) 0.0741(19) N7 0.0660(19) 0.0580(18) 0.107(3) 0.0172(17) 0.0380(19) 0.0056(15) C35 0.0509(17) 0.0522(19) 0.0589(19) 0.0001(15) 0.0049(14) -0.0013(14) C36 0.085(3) 0.086(3) 0.071(2) 0.012(2) 0.033(2) 0.013(2) C37 0.154(5) 0.075(3) 0.113(4) 0.013(3) 0.076(4) 0.000(3) O5 0.0729(16) 0.0614(16) 0.101(2) 0.0120(14) 0.0316(14) 0.0116(12) C39 0.165(5) 0.067(3) 0.223(7) 0.046(4) 0.130(5) 0.044(3) C38 0.150(5) 0.091(4) 0.173(6) 0.059(4) 0.097(4) 0.040(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 O2 1.420(2) . ? S1 O1 1.423(2) . ? S1 N6 1.576(3) . ? S1 C15 1.782(3) . ? N5 N4 1.355(3) . ? N5 C3 1.374(3) . ? N5 C12 1.434(3) . ? C15 C14 1.367(4) . ? C15 C16 1.383(4) . ? C3 C2 1.371(4) . ? C3 C5 1.472(4) . ? C14 C13 1.380(4) . ? C14 H14 0.9300 . ? C9 C8 1.377(4) . ? C9 C10 1.384(4) . ? C9 H9 0.9300 . ? C8 C7 1.386(4) . ? C8 C11 1.513(4) . ? O6 C40 1.242(4) . ? C5 C6 1.385(4) . ? C5 C10 1.391(4) . ? C2 C1 1.387(4) . ? C2 H2 0.9300 . ? N6 H6B 0.83(4) . ? N6 H6A 0.86(4) . ? C16 C17 1.374(4) . ? C16 H16 0.9300 . ? N4 C1 1.324(4) . ? C17 C12 1.368(4) . ? C17 H17 0.9300 . ? C12 C13 1.378(4) . ? C7 C6 1.377(4) . ? C7 H7 0.9300 . ? C13 H13 0.9300 . ? C40 N8 1.305(4) . ? C40 C41 1.495(4) . ? C10 H10 0.9300 . ? C1 C4 1.476(4) . ? F2 C4 1.291(4) . ? F3 C4 1.303(4) . ? C6 H6 0.9300 . ? N8 C44 1.463(5) . ? N8 H8A 0.83(3) . ? C41 C42 1.484(5) . ? C41 H41A 0.9700 . ? C41 H41B 0.9700 . ? C4 F1 1.271(4) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C43 C44 1.375(6) . ? C43 C42 1.397(6) . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? C42 H42A 0.9700 . ? C42 H42B 0.9700 . ? S2 O4 1.421(2) . ? S2 O3 1.424(2) . ? S2 N3 1.585(3) . ? S2 C32 1.776(3) . ? N2 N1 1.357(3) . ? N2 C20 1.370(3) . ? N2 C29 1.430(3) . ? C20 C19 1.374(4) . ? C20 C22 1.475(4) . ? C32 C31 1.377(4) . ? C32 C33 1.380(4) . ? C22 C23 1.387(4) . ? C22 C27 1.392(4) . ? N1 C18 1.321(3) . ? C31 C30 1.383(4) . ? C31 H31 0.9300 . ? C29 C34 1.368(4) . ? C29 C30 1.383(4) . ? F4 C21 1.323(4) . ? C24 C23 1.374(4) . ? C24 C25 1.389(4) . ? C24 H24 0.9300 . ? N3 H3A 0.88(3) . ? N3 H3B 0.83(4) . ? C26 C27 1.381(4) . ? C26 C25 1.382(4) . ? C26 H26 0.9300 . ? C25 C28 1.510(4) . ? F5 C21 1.306(3) . ? C34 C33 1.381(4) . ? C34 H34 0.9300 . ? C19 C18 1.387(4) . ? C19 H19 0.9300 . ? C18 C21 1.481(4) . ? C33 H33 0.9300 . ? C27 H27 0.9300 . ? C30 H30 0.9300 . ? C23 H23 0.9300 . ? C21 F6 1.303(4) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? N7 C35 1.303(4) . ? N7 C39 1.457(5) . ? N7 H7A 0.86(4) . ? C35 O5 1.252(4) . ? C35 C36 1.476(5) . ? C36 C37 1.492(6) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 C38 1.396(6) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C39 C38 1.319(6) . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C38 H38A 0.9700 . ? C38 H38B 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 O2 S1 O1 119.35(17) . . ? O2 S1 N6 106.68(17) . . ? O1 S1 N6 108.22(17) . . ? O2 S1 C15 107.76(13) . . ? O1 S1 C15 105.55(13) . . ? N6 S1 C15 108.99(14) . . ? N4 N5 C3 112.5(2) . . ? N4 N5 C12 117.0(2) . . ? C3 N5 C12 130.5(2) . . ? C14 C15 C16 120.3(2) . . ? C14 C15 S1 119.5(2) . . ? C16 C15 S1 120.1(2) . . ? C2 C3 N5 105.5(2) . . ? C2 C3 C5 128.8(2) . . ? N5 C3 C5 125.7(2) . . ? C15 C14 C13 120.0(3) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C8 C9 C10 121.8(3) . . ? C8 C9 H9 119.1 . . ? C10 C9 H9 119.1 . . ? C9 C8 C7 117.6(3) . . ? C9 C8 C11 121.6(3) . . ? C7 C8 C11 120.7(3) . . ? C6 C5 C10 118.4(3) . . ? C6 C5 C3 122.8(2) . . ? C10 C5 C3 118.7(2) . . ? C3 C2 C1 105.5(2) . . ? C3 C2 H2 127.3 . . ? C1 C2 H2 127.3 . . ? S1 N6 H6B 117(2) . . ? S1 N6 H6A 114(3) . . ? H6B N6 H6A 124(4) . . ? C17 C16 C15 119.7(3) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C1 N4 N5 103.8(2) . . ? C12 C17 C16 119.9(3) . . ? C12 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C17 C12 C13 120.6(2) . . ? C17 C12 N5 121.2(2) . . ? C13 C12 N5 118.2(2) . . ? C6 C7 C8 121.4(3) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C12 C13 C14 119.5(3) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? O6 C40 N8 121.0(3) . . ? O6 C40 C41 120.1(3) . . ? N8 C40 C41 119.0(3) . . ? C9 C10 C5 120.1(3) . . ? C9 C10 H10 120.0 . . ? C5 C10 H10 120.0 . . ? N4 C1 C2 112.8(3) . . ? N4 C1 C4 119.1(3) . . ? C2 C1 C4 128.1(3) . . ? C7 C6 C5 120.7(3) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C40 N8 C44 125.6(3) . . ? C40 N8 H8A 119(2) . . ? C44 N8 H8A 115(2) . . ? C42 C41 C40 116.0(3) . . ? C42 C41 H41A 108.3 . . ? C40 C41 H41A 108.3 . . ? C42 C41 H41B 108.3 . . ? C40 C41 H41B 108.3 . . ? H41A C41 H41B 107.4 . . ? F1 C4 F2 106.1(4) . . ? F1 C4 F3 106.0(3) . . ? F2 C4 F3 103.2(3) . . ? F1 C4 C1 114.9(3) . . ? F2 C4 C1 112.3(3) . . ? F3 C4 C1 113.5(3) . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C44 C43 C42 122.7(4) . . ? C44 C43 H43A 106.6 . . ? C42 C43 H43A 106.6 . . ? C44 C43 H43B 106.6 . . ? C42 C43 H43B 106.6 . . ? H43A C43 H43B 106.6 . . ? C43 C44 N8 115.7(4) . . ? C43 C44 H44A 108.4 . . ? N8 C44 H44A 108.4 . . ? C43 C44 H44B 108.4 . . ? N8 C44 H44B 108.4 . . ? H44A C44 H44B 107.4 . . ? C43 C42 C41 118.2(4) . . ? C43 C42 H42A 107.8 . . ? C41 C42 H42A 107.8 . . ? C43 C42 H42B 107.8 . . ? C41 C42 H42B 107.8 . . ? H42A C42 H42B 107.1 . . ? O4 S2 O3 119.70(17) . . ? O4 S2 N3 106.92(16) . . ? O3 S2 N3 107.69(17) . . ? O4 S2 C32 105.75(13) . . ? O3 S2 C32 107.29(14) . . ? N3 S2 C32 109.17(13) . . ? N1 N2 C20 112.4(2) . . ? N1 N2 C29 116.7(2) . . ? C20 N2 C29 130.5(2) . . ? N2 C20 C19 105.5(2) . . ? N2 C20 C22 125.7(2) . . ? C19 C20 C22 128.9(2) . . ? C31 C32 C33 121.1(2) . . ? C31 C32 S2 119.8(2) . . ? C33 C32 S2 119.1(2) . . ? C23 C22 C27 118.4(3) . . ? C23 C22 C20 122.9(2) . . ? C27 C22 C20 118.7(2) . . ? C18 N1 N2 104.0(2) . . ? C32 C31 C30 119.4(3) . . ? C32 C31 H31 120.3 . . ? C30 C31 H31 120.3 . . ? C34 C29 C30 120.7(2) . . ? C34 C29 N2 120.8(2) . . ? C30 C29 N2 118.5(2) . . ? C23 C24 C25 121.9(3) . . ? C23 C24 H24 119.1 . . ? C25 C24 H24 119.1 . . ? S2 N3 H3A 113(2) . . ? S2 N3 H3B 116(2) . . ? H3A N3 H3B 119(3) . . ? C27 C26 C25 121.3(3) . . ? C27 C26 H26 119.3 . . ? C25 C26 H26 119.3 . . ? C26 C25 C24 117.6(3) . . ? C26 C25 C28 121.3(3) . . ? C24 C25 C28 121.1(3) . . ? C29 C34 C33 120.2(3) . . ? C29 C34 H34 119.9 . . ? C33 C34 H34 119.9 . . ? C20 C19 C18 105.4(2) . . ? C20 C19 H19 127.3 . . ? C18 C19 H19 127.3 . . ? N1 C18 C19 112.7(2) . . ? N1 C18 C21 119.2(3) . . ? C19 C18 C21 128.1(2) . . ? C32 C33 C34 119.1(3) . . ? C32 C33 H33 120.4 . . ? C34 C33 H33 120.4 . . ? C26 C27 C22 120.6(3) . . ? C26 C27 H27 119.7 . . ? C22 C27 H27 119.7 . . ? C31 C30 C29 119.6(3) . . ? C31 C30 H30 120.2 . . ? C29 C30 H30 120.2 . . ? C24 C23 C22 120.3(3) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? F6 C21 F5 106.8(3) . . ? F6 C21 F4 105.6(3) . . ? F5 C21 F4 105.5(3) . . ? F6 C21 C18 113.1(3) . . ? F5 C21 C18 111.9(3) . . ? F4 C21 C18 113.4(3) . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C35 N7 C39 124.6(3) . . ? C35 N7 H7A 120(2) . . ? C39 N7 H7A 115(2) . . ? O5 C35 N7 121.0(3) . . ? O5 C35 C36 119.8(3) . . ? N7 C35 C36 119.1(3) . . ? C35 C36 C37 116.7(3) . . ? C35 C36 H36A 108.1 . . ? C37 C36 H36A 108.1 . . ? C35 C36 H36B 108.1 . . ? C37 C36 H36B 108.1 . . ? H36A C36 H36B 107.3 . . ? C38 C37 C36 117.5(4) . . ? C38 C37 H37A 107.9 . . ? C36 C37 H37A 107.9 . . ? C38 C37 H37B 107.9 . . ? C36 C37 H37B 107.9 . . ? H37A C37 H37B 107.2 . . ? C38 C39 N7 117.2(4) . . ? C38 C39 H39A 108.0 . . ? N7 C39 H39A 108.0 . . ? C38 C39 H39B 108.0 . . ? N7 C39 H39B 108.0 . . ? H39A C39 H39B 107.2 . . ? C39 C38 C37 124.7(4) . . ? C39 C38 H38A 106.1 . . ? C37 C38 H38A 106.1 . . ? C39 C38 H38B 106.1 . . ? C37 C38 H38B 106.1 . . ? H38A C38 H38B 106.3 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.859 _refine_diff_density_min -0.394 _refine_diff_density_rms 0.061 _database_code_depnum_ccdc_archive 'CCDC 954144' ####################################################################### # # 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_CEL-VLM-III _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Celecoxib-Valerolactam-Form-III _chemical_melting_point 381 _chemical_formula_moiety 'C17 H14 F3 N3 O2 S, C6 H11 N O' _chemical_formula_sum 'C22 H23 F3 N4 O3 S' _chemical_formula_weight 480.50 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 monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.8501(18) _cell_length_b 8.4190(11) _cell_length_c 17.761(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.901(2) _cell_angle_gamma 90.00 _cell_volume 2215.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3351 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 23.04 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 0.204 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23019 _diffrn_reflns_av_R_equivalents 0.0545 _diffrn_reflns_av_sigmaI/netI 0.0413 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 26.37 _reflns_number_total 4532 _reflns_number_gt 3832 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0674P)^2^+2.2486P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4532 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0998 _refine_ls_R_factor_gt 0.0850 _refine_ls_wR_factor_ref 0.1881 _refine_ls_wR_factor_gt 0.1802 _refine_ls_goodness_of_fit_ref 1.234 _refine_ls_restrained_S_all 1.234 _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 0.23964(6) 0.08721(11) 1.17115(5) 0.0367(3) Uani 1 1 d . . . F1 F 0.79974(15) 0.4217(3) 0.90876(13) 0.0629(7) Uani 1 1 d . . . N2 N 0.53120(18) 0.2735(3) 0.97454(15) 0.0294(6) Uani 1 1 d . . . C3 C 0.5315(2) 0.2828(4) 0.89721(18) 0.0293(7) Uani 1 1 d . . . C16 C 0.3311(2) 0.0705(4) 1.04249(19) 0.0316(7) Uani 1 1 d . . . H16 H 0.2881 -0.0044 1.0262 0.038 Uiso 1 1 calc R . . N1 N 0.61334(18) 0.3075(3) 1.00885(15) 0.0321(6) Uani 1 1 d . . . O1 O 0.19032(19) -0.0384(3) 1.13434(17) 0.0545(8) Uani 1 1 d . . . F3 F 0.80981(16) 0.2721(4) 1.00452(17) 0.0767(9) Uani 1 1 d . . . C2 C 0.6181(2) 0.3209(4) 0.88230(19) 0.0327(8) Uani 1 1 d . . . H2 H 0.6410 0.3341 0.8352 0.039 Uiso 1 1 calc R . . C17 C 0.3988(2) 0.1126(4) 0.99681(19) 0.0309(7) Uani 1 1 d . . . H17 H 0.4024 0.0646 0.9499 0.037 Uiso 1 1 calc R . . C13 C 0.4587(2) 0.2937(4) 1.0919(2) 0.0373(8) Uani 1 1 d . . . H13 H 0.5019 0.3681 1.1083 0.045 Uiso 1 1 calc R . . C1 C 0.6646(2) 0.3356(4) 0.95254(19) 0.0315(7) Uani 1 1 d . . . C15 C 0.3278(2) 0.1402(4) 1.11265(18) 0.0296(7) Uani 1 1 d . . . C12 C 0.4612(2) 0.2264(4) 1.02118(18) 0.0291(7) Uani 1 1 d . . . O2 O 0.2806(2) 0.0625(4) 1.24523(15) 0.0571(8) Uani 1 1 d . . . N3 N 0.1733(2) 0.2354(4) 1.1758(2) 0.0432(8) Uani 1 1 d . . . C4 C 0.7602(2) 0.3853(5) 0.9698(2) 0.0413(9) Uani 1 1 d . . . C5 C 0.4504(2) 0.2775(4) 0.84448(19) 0.0319(7) Uani 1 1 d . . . C7 C 0.2997(2) 0.3636(5) 0.8085(2) 0.0423(9) Uani 1 1 d . . . H7 H 0.2477 0.4166 0.8207 0.051 Uiso 1 1 calc R . . C6 C 0.3723(2) 0.3582(4) 0.8608(2) 0.0376(8) Uani 1 1 d . . . H6 H 0.3693 0.4085 0.9071 0.045 Uiso 1 1 calc R . . F2 F 0.76643(18) 0.5088(4) 1.01558(19) 0.0934(12) Uani 1 1 d . . . C14 C 0.3918(2) 0.2504(4) 1.13806(19) 0.0377(8) Uani 1 1 d . . . H14 H 0.3898 0.2949 1.1858 0.045 Uiso 1 1 calc R . . C10 C 0.4531(3) 0.2041(5) 0.7749(2) 0.0402(9) Uani 1 1 d . . . H10 H 0.5047 0.1494 0.7630 0.048 Uiso 1 1 calc R . . C8 C 0.3014(3) 0.2927(5) 0.7382(2) 0.0426(9) Uani 1 1 d . . . C9 C 0.3793(3) 0.2119(5) 0.7231(2) 0.0464(10) Uani 1 1 d . . . H9 H 0.3822 0.1614 0.6767 0.056 Uiso 1 1 calc R . . C11 C 0.2223(3) 0.3080(6) 0.6812(3) 0.0636(13) Uani 1 1 d . . . H11A H 0.1938 0.4092 0.6871 0.095 Uiso 1 1 calc R . . H11B H 0.1797 0.2248 0.6890 0.095 Uiso 1 1 calc R . . H11C H 0.2428 0.2997 0.6313 0.095 Uiso 1 1 calc R . . N4 N 0.0133(3) 0.3558(5) 0.9221(2) 0.0553(10) Uani 1 1 d . . . C18 C 0.0538(2) 0.2758(5) 0.9786(2) 0.0468(10) Uani 1 1 d . . . C22 C -0.0016(4) 0.3013(6) 0.8446(3) 0.0686(14) Uani 1 1 d . . . H22A H 0.0167 0.3844 0.8110 0.082 Uiso 1 1 calc R . . H22B H -0.0657 0.2830 0.8337 0.082 Uiso 1 1 calc R . . C21 C 0.0480(5) 0.1545(8) 0.8290(3) 0.0928(19) Uani 1 1 d . . . H21A H 0.0116 0.0943 0.7916 0.111 Uiso 1 1 calc R . . H21B H 0.1029 0.1846 0.8061 0.111 Uiso 1 1 calc R . . C20 C 0.0710(7) 0.0563(10) 0.8870(4) 0.153(4) Uani 1 1 d . . . H20A H 0.1206 -0.0091 0.8722 0.184 Uiso 1 1 calc R . . H20B H 0.0203 -0.0142 0.8929 0.184 Uiso 1 1 calc R . . C19 C 0.0973(4) 0.1221(6) 0.9608(3) 0.0696(14) Uani 1 1 d . . . H19A H 0.1622 0.1371 0.9645 0.084 Uiso 1 1 calc R . . H19B H 0.0832 0.0450 0.9988 0.084 Uiso 1 1 calc R . . O3 O 0.0576(2) 0.3260(4) 1.04438(18) 0.0607(8) Uani 1 1 d . . . H4A H -0.009(3) 0.450(6) 0.934(3) 0.060(14) Uiso 1 1 d . . . H3A H 0.142(2) 0.250(4) 1.137(2) 0.027(10) Uiso 1 1 d . . . H3B H 0.197(3) 0.314(5) 1.202(2) 0.037(11) Uiso 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 0.0368(5) 0.0410(5) 0.0334(5) 0.0083(4) 0.0109(4) -0.0054(4) F1 0.0436(13) 0.097(2) 0.0497(14) 0.0041(14) 0.0142(11) -0.0260(13) N2 0.0255(13) 0.0348(15) 0.0280(14) -0.0014(12) 0.0037(11) -0.0024(11) C3 0.0312(17) 0.0301(17) 0.0272(17) -0.0032(13) 0.0066(14) 0.0015(14) C16 0.0274(16) 0.0298(17) 0.0376(18) 0.0002(14) 0.0017(14) -0.0029(14) N1 0.0256(14) 0.0392(16) 0.0314(15) -0.0004(12) 0.0009(12) -0.0043(12) O1 0.0533(17) 0.0461(16) 0.0666(19) -0.0024(14) 0.0224(14) -0.0183(13) F3 0.0375(13) 0.105(2) 0.086(2) 0.0246(17) -0.0135(13) -0.0077(14) C2 0.0324(17) 0.0399(19) 0.0263(17) 0.0010(14) 0.0068(14) 0.0000(15) C17 0.0346(17) 0.0295(17) 0.0287(17) -0.0028(13) 0.0028(14) 0.0009(14) C13 0.0375(19) 0.042(2) 0.0332(19) -0.0065(16) 0.0044(15) -0.0116(16) C1 0.0290(16) 0.0309(17) 0.0355(18) -0.0016(14) 0.0090(14) -0.0032(14) C15 0.0255(15) 0.0327(17) 0.0311(17) 0.0080(14) 0.0056(13) -0.0002(14) C12 0.0274(16) 0.0296(17) 0.0308(17) 0.0029(14) 0.0052(13) 0.0009(13) O2 0.0616(18) 0.072(2) 0.0389(15) 0.0221(14) 0.0094(14) -0.0004(16) N3 0.0378(18) 0.054(2) 0.038(2) -0.0064(17) 0.0040(16) -0.0026(16) C4 0.0319(18) 0.053(2) 0.040(2) -0.0097(18) 0.0075(16) -0.0082(17) C5 0.0333(18) 0.0329(18) 0.0298(17) 0.0022(14) 0.0030(14) -0.0043(14) C7 0.0335(19) 0.049(2) 0.044(2) -0.0003(18) -0.0002(16) 0.0049(17) C6 0.0380(19) 0.043(2) 0.0321(18) -0.0079(16) 0.0030(15) 0.0029(16) F2 0.0523(16) 0.114(2) 0.118(3) -0.077(2) 0.0301(16) -0.0379(16) C14 0.042(2) 0.046(2) 0.0256(17) -0.0038(15) 0.0031(15) -0.0058(17) C10 0.040(2) 0.049(2) 0.0322(19) -0.0069(16) 0.0052(16) 0.0015(17) C8 0.042(2) 0.047(2) 0.037(2) 0.0054(17) -0.0082(17) -0.0089(17) C9 0.055(2) 0.056(2) 0.0284(19) -0.0064(17) 0.0023(17) -0.006(2) C11 0.059(3) 0.080(3) 0.050(3) -0.002(2) -0.014(2) -0.002(2) N4 0.056(2) 0.046(2) 0.061(2) -0.0041(18) -0.0129(18) 0.0065(18) C18 0.0305(19) 0.050(2) 0.058(3) -0.005(2) -0.0066(18) -0.0056(17) C22 0.075(3) 0.074(3) 0.055(3) 0.003(2) -0.007(3) 0.000(3) C21 0.099(5) 0.109(5) 0.070(4) -0.020(4) 0.003(3) 0.019(4) C20 0.245(11) 0.129(7) 0.080(5) -0.041(5) -0.035(6) 0.111(7) C19 0.068(3) 0.063(3) 0.076(3) -0.007(3) -0.006(3) 0.025(3) O3 0.0620(19) 0.0580(19) 0.059(2) -0.0095(15) -0.0167(15) 0.0067(15) _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 O1 1.420(3) . ? S1 O2 1.427(3) . ? S1 N3 1.595(4) . ? S1 C15 1.782(3) . ? F1 C4 1.304(4) . ? N2 N1 1.356(4) . ? N2 C3 1.376(4) . ? N2 C12 1.428(4) . ? C3 C2 1.369(4) . ? C3 C5 1.476(5) . ? C16 C17 1.380(5) . ? C16 C15 1.382(5) . ? C16 H16 0.9300 . ? N1 C1 1.319(4) . ? F3 C4 1.330(5) . ? C2 C1 1.390(5) . ? C2 H2 0.9300 . ? C17 C12 1.382(5) . ? C17 H17 0.9300 . ? C13 C14 1.379(5) . ? C13 C12 1.380(5) . ? C13 H13 0.9300 . ? C1 C4 1.493(5) . ? C15 C14 1.382(5) . ? N3 H3A 0.81(4) . ? N3 H3B 0.87(4) . ? C4 F2 1.319(4) . ? C5 C10 1.384(5) . ? C5 C6 1.391(5) . ? C7 C6 1.376(5) . ? C7 C8 1.385(5) . ? C7 H7 0.9300 . ? C6 H6 0.9300 . ? C14 H14 0.9300 . ? C10 C9 1.384(5) . ? C10 H10 0.9300 . ? C8 C9 1.384(6) . ? C8 C11 1.504(5) . ? C9 H9 0.9300 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? N4 C18 1.320(5) . ? N4 C22 1.454(6) . ? N4 H4A 0.89(5) . ? C18 O3 1.240(5) . ? C18 C19 1.490(6) . ? C22 C21 1.475(8) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C21 C20 1.347(9) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C20 C19 1.452(8) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 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 O1 S1 O2 119.34(19) . . ? O1 S1 N3 107.8(2) . . ? O2 S1 N3 107.0(2) . . ? O1 S1 C15 107.12(17) . . ? O2 S1 C15 106.88(17) . . ? N3 S1 C15 108.36(17) . . ? N1 N2 C3 111.9(3) . . ? N1 N2 C12 117.7(3) . . ? C3 N2 C12 130.3(3) . . ? C2 C3 N2 105.9(3) . . ? C2 C3 C5 128.4(3) . . ? N2 C3 C5 125.0(3) . . ? C17 C16 C15 119.6(3) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C1 N1 N2 104.2(3) . . ? C3 C2 C1 105.2(3) . . ? C3 C2 H2 127.4 . . ? C1 C2 H2 127.4 . . ? C16 C17 C12 119.6(3) . . ? C16 C17 H17 120.2 . . ? C12 C17 H17 120.2 . . ? C14 C13 C12 119.9(3) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? N1 C1 C2 112.8(3) . . ? N1 C1 C4 119.0(3) . . ? C2 C1 C4 128.1(3) . . ? C16 C15 C14 120.9(3) . . ? C16 C15 S1 119.5(3) . . ? C14 C15 S1 119.6(3) . . ? C13 C12 C17 120.7(3) . . ? C13 C12 N2 118.7(3) . . ? C17 C12 N2 120.6(3) . . ? S1 N3 H3A 113(3) . . ? S1 N3 H3B 113(3) . . ? H3A N3 H3B 122(4) . . ? F1 C4 F2 108.1(3) . . ? F1 C4 F3 106.7(3) . . ? F2 C4 F3 105.4(3) . . ? F1 C4 C1 111.8(3) . . ? F2 C4 C1 111.9(3) . . ? F3 C4 C1 112.5(3) . . ? C10 C5 C6 118.6(3) . . ? C10 C5 C3 120.5(3) . . ? C6 C5 C3 120.6(3) . . ? C6 C7 C8 122.1(4) . . ? C6 C7 H7 118.9 . . ? C8 C7 H7 118.9 . . ? C7 C6 C5 120.2(3) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C13 C14 C15 119.4(3) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C9 C10 C5 120.2(4) . . ? C9 C10 H10 119.9 . . ? C5 C10 H10 119.9 . . ? C9 C8 C7 117.0(3) . . ? C9 C8 C11 122.5(4) . . ? C7 C8 C11 120.5(4) . . ? C10 C9 C8 121.9(3) . . ? C10 C9 H9 119.1 . . ? C8 C9 H9 119.1 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C18 N4 C22 126.3(4) . . ? C18 N4 H4A 116(3) . . ? C22 N4 H4A 118(3) . . ? O3 C18 N4 122.1(4) . . ? O3 C18 C19 120.3(4) . . ? N4 C18 C19 117.6(4) . . ? N4 C22 C21 113.4(4) . . ? N4 C22 H22A 108.9 . . ? C21 C22 H22A 108.9 . . ? N4 C22 H22B 108.9 . . ? C21 C22 H22B 108.9 . . ? H22A C22 H22B 107.7 . . ? C20 C21 C22 118.4(6) . . ? C20 C21 H21A 107.7 . . ? C22 C21 H21A 107.7 . . ? C20 C21 H21B 107.7 . . ? C22 C21 H21B 107.7 . . ? H21A C21 H21B 107.1 . . ? C21 C20 C19 119.7(7) . . ? C21 C20 H20A 107.4 . . ? C19 C20 H20A 107.4 . . ? C21 C20 H20B 107.4 . . ? C19 C20 H20B 107.4 . . ? H20A C20 H20B 106.9 . . ? C20 C19 C18 115.5(5) . . ? C20 C19 H19A 108.4 . . ? C18 C19 H19A 108.4 . . ? C20 C19 H19B 108.4 . . ? C18 C19 H19B 108.4 . . ? H19A C19 H19B 107.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.623 _refine_diff_density_min -0.354 _refine_diff_density_rms 0.065 _database_code_depnum_ccdc_archive 'CCDC 954145'