#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/91/2009109.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2009109
loop_
_publ_author_name
'Jain, Subhash C.'
'Sinha, Juhi'
'Bhagat, Sunita'
'Babu, B. Ravindra'
'Bali, Shilpika'
_publ_section_title
3'-(2,3-Dimethyl-5-oxo-1-phenyl-3-pyrazolin-4-yl)-5-fluorospiro[3H-indole-3,2'-thiazolidine]-2(1H),4'-dione
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1826
_journal_page_last               1829
_journal_paper_doi               10.1107/S010827019900966X
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C21 H17 F N4 O3 S'
_chemical_formula_weight         424.45
_chemical_name_systematic
;
 3'-(2,3-Dimethyl-5-oxo-1-phenyl-3-pyrazolin-4-yl) Spiro
(5-fluoro-3H-indol-3,2'-thiazolidine)-2,4'-(1H)-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 110.7440(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1159(5)
_cell_length_b                   15.5291(7)
_cell_length_c                   13.3630(6)
_cell_measurement_reflns_used    7633
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      28.44
_cell_measurement_theta_min      2.09
_cell_volume                     1963.12(16)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1994a)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL/PC (Siemens, 1994b)'
_diffrn_ambient_temperature      180(2)
_diffrn_measurement_device       'Siemens SMART CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.020
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11442
_diffrn_reflns_theta_max         28.44
_diffrn_reflns_theta_min         2.09
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.295
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.030
_refine_ls_goodness_of_fit_obs   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4600
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_restrained_S_obs      1.094
_refine_ls_R_factor_all          0.053
_refine_ls_R_factor_obs          .037
_refine_ls_shift/esd_max         <0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0503P)²+0.2465P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.097
_refine_ls_wR_factor_obs         .090
_reflns_number_observed          3566
_reflns_number_total             4600
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            cf1329.cif
_cod_data_source_block           js104
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0503P)^2^+0.2465P] where P = (Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0503P)^2^+0.2465P] where P = (Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2009109
_cod_database_fobs_code          2009109
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'
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_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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C10 S1 C3 92.51(7) y
C2 N1 C8 112.09(12) ?
C11 N2 C12 118.88(11) ?
C11 N2 C3 118.11(11) ?
C12 N2 C3 122.17(11) ?
C13 N3 N4 109.39(10) ?
C13 N3 C15 128.98(12) ?
N4 N3 C15 119.00(11) ?
N3 N4 C16 107.76(10) ?
N3 N4 C17 117.86(10) ?
C16 N4 C17 120.86(11) ?
O1 C2 N1 127.88(14) ?
O1 C2 C3 125.43(13) ?
N1 C2 C3 106.66(12) ?
N2 C3 C9 118.80(11) y
N2 C3 C2 113.08(11) y
C9 C3 C2 102.93(11) y
N2 C3 S1 105.30(9) y
C9 C3 S1 108.91(9) y
C2 C3 S1 107.39(9) y
C9 C4 C5 116.17(14) ?
F1 C5 C6 118.39(15) ?
F1 C5 C4 117.73(15) ?
C6 C5 C4 123.87(15) ?
C5 C6 C7 119.54(15) ?
C8 C7 C6 117.68(15) ?
C7 C8 C9 121.65(14) ?
C7 C8 N1 128.15(14) ?
C9 C8 N1 110.20(12) ?
C4 C9 C8 121.05(13) ?
C4 C9 C3 131.35(13) ?
C8 C9 C3 107.37(12) ?
C11 C10 S1 106.81(10) ?
O2 C11 N2 123.96(13) ?
O2 C11 C10 124.24(13) ?
N2 C11 C10 111.76(12) ?
C13 C12 N2 128.28(12) ?
C13 C12 C16 108.79(12) ?
N2 C12 C16 121.40(11) ?
N3 C13 C12 108.27(12) ?
N3 C13 C14 122.06(12) ?
C12 C13 C14 129.67(12) ?
O3 C16 N4 123.99(12) ?
O3 C16 C12 130.56(13) ?
N4 C16 C12 105.42(11) ?
C18 C17 C22 120.82(13) ?
C18 C17 N4 119.51(13) ?
C22 C17 N4 119.62(13) ?
C17 C18 C19 119.07(15) ?
C20 C19 C18 120.46(16) ?
C19 C20 C21 120.18(15) ?
C20 C21 C22 119.95(16) ?
C21 C22 C17 119.51(15) ?
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) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A O3 2_755 0.88 1.85 2.7002(15) 161
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
C13 N3 N4 C16 -5.60(14) ?
C15 N3 N4 C16 -168.85(12) ?
C13 N3 N4 C17 -146.72(12) ?
C15 N3 N4 C17 50.03(16) ?
C8 N1 C2 O1 177.04(14) ?
C8 N1 C2 C3 -4.82(15) ?
C11 N2 C3 C9 -131.66(13) ?
C12 N2 C3 C9 37.69(17) ?
C11 N2 C3 C2 107.56(13) ?
C12 N2 C3 C2 -83.09(15) ?
C11 N2 C3 S1 -9.41(14) ?
C12 N2 C3 S1 159.95(10) ?
O1 C2 C3 N2 -44.35(19) ?
N1 C2 C3 N2 137.46(12) ?
O1 C2 C3 C9 -173.77(14) ?
N1 C2 C3 C9 8.03(14) ?
O1 C2 C3 S1 71.37(16) ?
N1 C2 C3 S1 -106.82(11) ?
C10 S1 C3 N2 18.13(11) ?
C10 S1 C3 C9 146.56(11) ?
C10 S1 C3 C2 -102.64(11) ?
C9 C4 C5 F1 179.68(12) ?
C9 C4 C5 C6 -0.5(2) ?
F1 C5 C6 C7 -178.93(13) ?
C4 C5 C6 C7 1.2(2) ?
C5 C6 C7 C8 -0.3(2) ?
C6 C7 C8 C9 -1.3(2) ?
C6 C7 C8 N1 179.75(13) ?
C2 N1 C8 C7 178.32(14) ?
C2 N1 C8 C9 -0.74(16) ?
C5 C4 C9 C8 -1.1(2) ?
C5 C4 C9 C3 172.56(13) ?
C7 C8 C9 C4 2.1(2) ?
N1 C8 C9 C4 -178.80(12) ?
C7 C8 C9 C3 -172.98(12) ?
N1 C8 C9 C3 6.15(15) ?
N2 C3 C9 C4 51.4(2) ?
C2 C3 C9 C4 177.21(14) ?
S1 C3 C9 C4 -69.04(17) ?
N2 C3 C9 C8 -134.26(12) ?
C2 C3 C9 C8 -8.44(14) ?
S1 C3 C9 C8 105.31(11) ?
C3 S1 C10 C11 -21.89(12) ?
C12 N2 C11 O2 5.3(2) ?
C3 N2 C11 O2 174.98(13) ?
C12 N2 C11 C10 -176.78(12) ?
C3 N2 C11 C10 -7.07(18) ?
S1 C10 C11 O2 -161.55(13) ?
S1 C10 C11 N2 20.51(16) ?
C11 N2 C12 C13 -92.71(17) ?
C3 N2 C12 C13 98.02(17) y
C11 N2 C12 C16 71.49(17) ?
C3 N2 C12 C16 -97.79(16) y
N4 N3 C13 C12 2.67(15) ?
C15 N3 C13 C12 163.74(13) ?
N4 N3 C13 C14 -177.42(12) ?
C15 N3 C13 C14 -16.3(2) ?
N2 C12 C13 N3 167.04(13) ?
C16 C12 C13 N3 1.25(15) ?
N2 C12 C13 C14 -12.9(2) ?
C16 C12 C13 C14 -178.65(13) ?
N3 N4 C16 O3 -171.93(13) ?
C17 N4 C16 O3 -32.2(2) ?
N3 N4 C16 C12 6.10(14) ?
C17 N4 C16 C12 145.83(12) ?
C13 C12 C16 O3 173.26(14) ?
N2 C12 C16 O3 6.3(2) ?
C13 C12 C16 N4 -4.59(15) ?
N2 C12 C16 N4 -171.54(11) ?
N3 N4 C17 C18 -128.04(14) ?
C16 N4 C17 C18 96.09(16) y
N3 N4 C17 C22 54.56(17) y
C16 N4 C17 C22 -81.31(17) y
C22 C17 C18 C19 0.4(2) ?
N4 C17 C18 C19 -176.97(13) ?
C17 C18 C19 C20 -1.2(2) ?
C18 C19 C20 C21 0.8(3) ?
C19 C20 C21 C22 0.4(3) ?
C20 C21 C22 C17 -1.1(2) ?
C18 C17 C22 C21 0.7(2) ?
N4 C17 C22 C21 178.10(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4425255
