data_2009109 _journal_name_full 'Acta Crystallographica' _journal_year 1999 _journal_volume C55 _journal_page_first 1826 _journal_page_last 1829 _publ_section_title ; 3'-(2,3-Dimethyl-5-oxo-1-phenyl-3-pyrazolin-4-yl)-5-fluoro- spiro[3H-indole-3,2'-thiazolidine]-2(1H),4'-dione ; loop_ _publ_author_name 'Jain, Subhash C.' 'Sinha, Juhi' 'Bhagat, Sunita' 'Babu, B. Ravindra' 'Bali, Shilpika' _chemical_formula_sum 'C21 H17 F N4 O3 S' _chemical_formula_weight 424.45 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.1159(5) _cell_length_b 15.5291(7) _cell_length_c 13.3630(6) _cell_angle_alpha 90.00 _cell_angle_beta 110.7440(10) _cell_angle_gamma 90.00 _cell_volume 1963.12(16) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _exptl_crystal_density_diffrn 1.436 _diffrn_ambient_temperature 180(2) _refine_ls_R_factor_obs .037 _refine_ls_wR_factor_obs .090 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol S1 .90704(4) .08981(3) .08156(3) .04236(13) Uani d . 1 . S F1 1.42084(11) -.04095(7) .08458(8) .0528(3) Uani d . 1 . F O1 .99382(13) .24940(7) .25473(10) .0435(3) Uani d . 1 . O O2 .89781(12) -.02488(7) .33098(9) .0395(3) Uani d . 1 . O O3 1.21320(11) -.10229(6) .32329(8) .0331(2) Uani d . 1 . O N1 1.17587(13) .24169(8) .18925(10) .0329(3) Uani d . 1 . N H1A 1.1954 .2969 .1888 .039 Uiso calc R 1 . H N2 1.04956(11) .06129(7) .28498(8) .0231(2) Uani d . 1 . N N3 1.30424(12) .02733(7) .54721(9) .0258(3) Uani d . 1 . N N4 1.32594(12) -.04616(7) .49437(9) .0258(3) Uani d . 1 . N C2 1.07202(15) .20992(9) .21993(11) .0301(3) Uani d . 1 . C C3 1.06652(14) .11144(9) .19885(10) .0254(3) Uani d . 1 . C C4 1.25109(16) .02163(10) .14521(11) .0312(3) Uani d . 1 . C H4A 1.2160 -.0336 .1535 .037 Uiso calc R 1 . H C5 1.36167(17) .03179(11) .10854(12) .0368(4) Uani d . 1 . C C6 1.41514(16) .11033(12) .09461(12) .0402(4) Uani d . 1 . C H6A 1.4903 .1135 .0678 .048 Uiso calc R 1 . H C7 1.35857(16) .18505(11) .12001(12) .0376(4) Uani d . 1 . C H7A 1.3940 .2401 .1114 .045 Uiso calc R 1 . H C8 1.24904(15) .17652(9) .15818(11) .0290(3) Uani d . 1 . C C9 1.19449(14) .09627(9) .16909(10) .0260(3) Uani d . 1 . C C10 .81242(16) .05022(12) .16237(13) .0411(4) Uani d . 1 . C H10A .7509 .0958 .1738 .049 Uiso calc R 1 . H H10B .7526 .0006 .1271 .049 Uiso calc R 1 . H C11 .92151(15) .02300(9) .26776(11) .0282(3) Uani d . 1 . C C12 1.16548(14) .03914(8) .37782(10) .0223(3) Uani d . 1 . C C13 1.21095(14) .07929(8) .47656(10) .0232(3) Uani d . 1 . C C14 1.17067(16) .16451(9) .50795(12) .0320(3) Uani d . 1 . C H14A 1.1314 .1566 .5646 .048 Uiso calc R 1 . H H14B 1.0997 .1915 .4457 .048 Uiso calc R 1 . H H14C 1.2544 .2015 .5342 .048 Uiso calc R 1 . H C15 1.40563(16) .04779(10) .65294(11) .0330(3) Uani d . 1 . C H15A 1.3783 .1018 .6782 .050 Uiso calc R 1 . H H15B 1.5000 .0540 .6489 .050 Uiso calc R 1 . H H15C 1.4067 .0013 .7028 .050 Uiso calc R 1 . H C16 1.23177(14) -.04251(8) .38845(11) .0247(3) Uani d . 1 . C C17 1.35368(15) -.12642(9) .55259(11) .0263(3) Uani d . 1 . C C18 1.47010(16) -.17456(10) .55719(12) .0333(3) Uani d . 1 . C H18A 1.5344 -.1540 .5253 .040 Uiso calc R 1 . H C19 1.49217(18) -.25360(10) .60907(13) .0422(4) Uani d . 1 . C H19A 1.5711 -.2878 .6116 .051 Uiso calc R 1 . H C20 1.4006(2) -.28270(10) .65686(13) .0456(4) Uani d . 1 . C H20A 1.4171 -.3365 .6930 .055 Uiso calc R 1 . H C21 1.2847(2) -.23395(11) .65252(13) .0454(4) Uani d . 1 . C H21A 1.2218 -.2540 .6860 .054 Uiso calc R 1 . H C22 1.26004(17) -.15573(10) .59942(12) .0359(3) Uani d . 1 . C H22A 1.1795 -.1224 .5951 .043 Uiso calc R 1 . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 .0322(2) .0620(3) .0249(2) -.01191(18) .00028(15) .00766(18) F1 .0570(7) .0624(7) .0439(6) .0206(5) .0239(5) -.0033(5) O1 .0499(7) .0306(6) .0580(7) .0120(5) .0290(6) .0100(5) O2 .0358(6) .0459(6) .0391(6) -.0088(5) .0159(5) .0079(5) O3 .0472(6) .0235(5) .0269(5) .0059(4) .0111(5) -.0027(4) N1 .0374(7) .0235(6) .0380(7) -.0033(5) .0136(6) .0050(5) N2 .0235(6) .0228(5) .0215(6) -.0013(4) .0061(4) .0025(4) N3 .0284(6) .0241(6) .0220(6) -.0012(5) .0053(5) -.0025(4) N4 .0288(6) .0240(6) .0228(6) .0033(5) .0070(5) .0012(4) C2 .0321(8) .0277(7) .0284(7) .0029(6) .0080(6) .0079(6) C3 .0254(7) .0263(7) .0216(7) -.0011(5) .0048(5) .0036(5) C4 .0366(8) .0340(8) .0207(7) .0002(6) .0073(6) -.0011(6) C5 .0364(8) .0488(10) .0235(7) .0112(7) .0084(6) .0004(6) C6 .0286(8) .0642(11) .0279(8) .0012(7) .0102(6) .0057(7) C7 .0317(8) .0465(9) .0330(8) -.0072(7) .0093(7) .0069(7) C8 .0270(7) .0329(8) .0243(7) -.0023(6) .0054(6) .0041(6) C9 .0270(7) .0303(7) .0183(6) -.0018(5) .0050(5) .0018(5) C10 .0270(8) .0558(10) .0355(9) -.0066(7) .0050(7) .0058(7) C11 .0261(7) .0291(7) .0295(7) -.0017(6) .0097(6) -.0010(6) C12 .0245(7) .0213(6) .0208(6) -.0004(5) .0076(5) .0009(5) C13 .0236(6) .0223(6) .0248(7) -.0037(5) .0099(5) .0006(5) C14 .0401(8) .0244(7) .0321(8) .0003(6) .0135(6) -.0031(6) C15 .0306(8) .0374(8) .0251(7) -.0066(6) .0024(6) -.0014(6) C16 .0260(7) .0249(7) .0241(7) .0003(5) .0099(5) .0025(5) C17 .0277(7) .0249(7) .0231(7) .0019(5) .0051(5) .0032(5) C18 .0295(8) .0357(8) .0314(8) .0046(6) .0068(6) .0016(6) C19 .0441(10) .0334(8) .0389(9) .0121(7) .0021(7) .0023(7) C20 .0658(12) .0286(8) .0331(8) .0005(8) .0061(8) .0072(7) C21 .0607(11) .0404(9) .0391(9) -.0091(8) .0226(8) .0063(7) C22 .0386(9) .0343(8) .0386(9) .0000(6) .0182(7) .0024(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 C10 . 1.7867(17) y S1 C3 . 1.8388(13) y F1 C5 . 1.3685(18) y O1 C2 . 1.2159(18) y O2 C11 . 1.2114(17) y O3 C16 . 1.2406(16) y N1 C2 . 1.3492(19) ? N1 C8 . 1.4007(19) ? N2 C11 . 1.3686(18) y N2 C12 . 1.4149(16) y N2 C3 . 1.4494(17) y N3 C13 . 1.3424(17) ? N3 N4 . 1.3997(15) ? N3 C15 . 1.4569(17) ? N4 C16 . 1.3996(16) ? N4 C17 . 1.4432(17) ? C2 C3 . 1.552(2) ? C3 C9 . 1.501(2) ? C4 C9 . 1.379(2) ? C4 C5 . 1.380(2) ? C5 C6 . 1.373(2) ? C6 C7 . 1.388(2) ? C7 C8 . 1.381(2) ? C8 C9 . 1.3913(19) ? C10 C11 . 1.510(2) ? C12 C13 . 1.3825(18) ? C12 C16 . 1.4177(18) ? C13 C14 . 1.4882(19) ? C17 C18 . 1.378(2) ? C17 C22 . 1.384(2) ? C18 C19 . 1.388(2) ? C19 C20 . 1.375(3) ? C20 C21 . 1.379(3) ? C21 C22 . 1.384(2) ?