#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/23/2012398.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_2012398
loop_
_publ_author_name
'Usman, Anwar'
'Razak, Ibrahim Abdul'
'Chantrapromma, Suchada'
'Fun, Hoong-Kun'
'Ray, Jayanta Kumar'
'Das Adhikari, Sujit'
'Datta, Bishnu Pada'
_publ_section_title
;
 Diethyl
 1-(p-fluorophenyl)-5-oxo-3-(2-thienyl)pyrrolidine-2,2-dicarboxylate
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1441
_journal_page_last               1442
_journal_paper_doi               10.1107/S010827010101681X
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C20 H20 F N O5 S'
_chemical_formula_moiety         'C20 H20 F N O5 S'
_chemical_formula_sum            'C20 H20 F N O5 S'
_chemical_formula_weight         405.43
_chemical_name_systematic
;
Diethyl 1-(p-fluorophenyl)-5-oxo-3-(2-thienyl)pyrrolidine-2,2-dicarboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                110.7040(10)
_cell_angle_beta                 92.6590(10)
_cell_angle_gamma                115.8560(10)
_cell_formula_units_Z            2
_cell_length_a                   9.6560(2)
_cell_length_b                   10.11950(10)
_cell_length_c                   12.3126(2)
_cell_measurement_reflns_used    3864
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.56
_cell_measurement_theta_min      1.82
_cell_volume                     983.58(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full .979
_diffrn_measured_fraction_theta_max .979
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0447
_diffrn_reflns_av_sigmaI/netI    .0773
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5604
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.82
_diffrn_standards_decay_%        negligible
_diffrn_standards_interval_count none
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .205
_exptl_absorpt_correction_T_max  .9679
_exptl_absorpt_correction_T_min  .9188
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             424
_exptl_crystal_size_max          .42
_exptl_crystal_size_mid          .32
_exptl_crystal_size_min          .16
_refine_diff_density_max         .349
_refine_diff_density_min         -.441
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   .945
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3391
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .945
_refine_ls_R_factor_all          .0778
_refine_ls_R_factor_gt           .0586
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.096P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .1491
_refine_ls_wR_factor_ref         .1608
_reflns_number_gt                2358
_reflns_number_total             3391
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk1510.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2012398
_cod_database_fobs_code          2012398
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
S1 .09020(9) .42654(8) .36062(7) .0538(3) Uani d . 1 A . S
F1 -.8995(3) -.6360(3) .0284(2) .1039(8) Uani d . 1 . . F
O1 -.4219(2) -.1151(2) .49515(18) .0609(6) Uani d . 1 . . O
O2 -.2608(2) .1873(2) .20841(17) .0499(5) Uani d . 1 . . O
O3 -.3428(3) -.0689(2) .08644(18) .0656(6) Uani d . 1 . . O
O4 -.0970(3) -.1343(3) .2981(2) .0696(7) Uani d . 1 . . O
O5 -.0139(2) .0271(2) .2020(2) .0623(6) Uani d . 1 . . O
N1 -.3565(2) -.0818(2) .32687(18) .0385(5) Uani d . 1 A . N
C1 -.4900(3) -.3678(3) .1864(3) .0541(7) Uani d . 1 . . C
H1A -.3951 -.3700 .1965 .065 Uiso calc R 1 . . H
C2 -.6275(4) -.5069(4) .1116(3) .0648(9) Uani d . 1 . . C
H2A -.6257 -.6025 .0698 .078 Uiso calc R 1 . . H
C3 -.7642(4) -.5000(4) .1010(3) .0640(9) Uani d . 1 . . C
C4 -.7720(4) -.3616(4) .1586(3) .0644(9) Uani d . 1 . . C
H4A -.8676 -.3607 .1488 .077 Uiso calc R 1 . . H
C5 -.6352(3) -.2232(4) .2317(3) .0518(7) Uani d . 1 . . C
H5A -.6376 -.1275 .2718 .062 Uiso calc R 1 . . H
C6 -.4948(3) -.2274(3) .2450(2) .0394(6) Uani d . 1 . . C
C7 -.3332(3) -.0375(3) .4479(2) .0440(6) Uani d . 1 . . C
C8 -.1802(3) .1185(3) .5078(2) .0470(7) Uani d . 1 . . C
H8A -.0966 .1000 .5338 .056 Uiso calc R 1 . . H
H8B -.1924 .1938 .5765 .056 Uiso calc R 1 . . H
C9 -.1432(3) .1832(3) .4114(2) .0357(6) Uani d . 1 A . C
H9A -.2019 .2419 .4128 .043 Uiso calc R 1 . . H
C10 -.2229(3) .0244(3) .2924(2) .0335(5) Uani d . 1 . . C
C11 -.2825(3) .0410(3) .1830(2) .0389(6) Uani d . 1 A . C
C12 -.3036(4) .2198(4) .1086(3) .0647(9) Uani d . 1 . . C
H12A -.2372 .2093 .0529 .078 Uiso calc R 1 . . H
H12B -.4133 .1433 .0664 .078 Uiso calc R 1 . . H
C13 -.2807(5) .3832(5) .1572(4) .0902(13) Uani d . 1 . . C
H13A -.3108 .4063 .0936 .135 Uiso calc R 1 . . H
H13B -.1712 .4582 .1967 .135 Uiso calc R 1 . . H
H13C -.3449 .3932 .2136 .135 Uiso calc R 1 . . H
C14 -.1066(3) -.0411(3) .2632(2) .0427(6) Uani d . 1 A . C
C15A .1305(14) .0007(14) .2144(19) .054(3) Uani d P .44(3) A 1 C
H15A .1762 .0315 .2970 .065 Uiso calc PR .44(3) A 1 H
H15B .1047 -.1100 .1665 .065 Uiso calc PR .44(3) A 1 H
C16A .236(2) .114(2) .166(3) .098(6) Uani d P .44(3) A 1 C
H16A .3345 .1124 .1679 .147 Uiso calc PR .44(3) A 1 H
H16B .2551 .2214 .2136 .147 Uiso calc PR .44(3) A 1 H
H16C .1853 .0811 .0849 .147 Uiso calc PR .44(3) A 1 H
C15B .1098(13) -.0059(12) .1538(18) .067(3) Uani d P .56(3) A 2 C
H15C .1019 -.0147 .0725 .081 Uiso calc PR .56(3) A 2 H
H15D .0958 -.1073 .1528 .081 Uiso calc PR .56(3) A 2 H
C16B .2680(12) .1277(14) .2299(15) .074(3) Uani d P .56(3) A 2 C
H16D .3492 .1086 .1970 .112 Uiso calc PR .56(3) A 2 H
H16E .2771 .1326 .3094 .112 Uiso calc PR .56(3) A 2 H
H16F .2800 .2281 .2325 .112 Uiso calc PR .56(3) A 2 H
C17 .0285(3) .2981(3) .4312(2) .0372(6) Uani d . 1 . . C
C18 .1550(3) .3283(4) .5096(3) .0515(7) Uani d . 1 A . C
H18A .1472 .2719 .5566 .062 Uiso calc R 1 . . H
C19 .2994(4) .4552(4) .5111(3) .0677(9) Uani d . 1 . . C
H19A .3964 .4906 .5594 .081 Uiso calc R 1 A . H
C20 .2827(4) .5190(4) .4363(3) .0632(9) Uani d . 1 A . C
H20B .3656 .6032 .4269 .076 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 .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F .0171 .0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .1246 .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
C20 S1 C17 92.45(14) yes
C11 O2 C12 117.1(2) ?
C14 O5 C15B 127.4(7) ?
C14 O5 C15A 106.2(7) ?
C7 N1 C6 121.00(19) yes
C7 N1 C10 113.42(19) ?
C6 N1 C10 125.37(19) ?
C6 C1 C2 119.7(3) ?
C6 C1 H1A 120.1 ?
C2 C1 H1A 120.1 ?
C3 C2 C1 118.5(3) ?
C3 C2 H2A 120.7 ?
C1 C2 H2A 120.7 ?
C2 C3 F1 118.8(3) ?
C2 C3 C4 122.8(3) ?
F1 C3 C4 118.4(3) ?
C3 C4 C5 118.7(3) ?
C3 C4 H4A 120.7 ?
C5 C4 H4A 120.7 ?
C6 C5 C4 119.7(3) ?
C6 C5 H5A 120.2 ?
C4 C5 H5A 120.2 ?
C1 C6 C5 120.6(3) ?
C1 C6 N1 121.7(2) ?
C5 C6 N1 117.6(2) ?
O1 C7 N1 124.4(2) ?
O1 C7 C8 127.5(3) ?
N1 C7 C8 108.0(2) yes
C7 C8 C9 104.5(2) ?
C7 C8 H8A 110.8 ?
C9 C8 H8A 110.8 ?
C7 C8 H8B 110.8 ?
C9 C8 H8B 110.8 ?
H8A C8 H8B 108.9 ?
C17 C9 C8 113.9(2) ?
C17 C9 C10 117.5(2) ?
C8 C9 C10 102.68(18) yes
C17 C9 H9A 107.4 ?
C8 C9 H9A 107.4 ?
C10 C9 H9A 107.4 ?
N1 C10 C11 110.58(19) ?
N1 C10 C14 111.24(19) ?
C11 C10 C14 108.8(2) ?
N1 C10 C9 101.06(18) yes
C11 C10 C9 115.42(19) ?
C14 C10 C9 109.59(19) ?
O3 C11 O2 124.9(2) ?
O3 C11 C10 122.6(2) ?
O2 C11 C10 112.5(2) ?
C13 C12 O2 108.0(3) ?
C13 C12 H12A 110.1 ?
O2 C12 H12A 110.1 ?
C13 C12 H12B 110.1 ?
O2 C12 H12B 110.1 ?
H12A C12 H12B 108.4 ?
C12 C13 H13A 109.5 ?
C12 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
C12 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
O4 C14 O5 125.6(3) ?
O4 C14 C10 123.8(3) ?
O5 C14 C10 110.4(2) ?
C16A C15A O5 98.9(15) ?
C16A C15A H15A 112.0 ?
O5 C15A H15A 112.0 ?
C16A C15A H15B 112.0 ?
O5 C15A H15B 112.0 ?
H15A C15A H15B 109.7 ?
C15A C16A H16A 109.5 ?
C15A C16A H16B 109.5 ?
H16A C16A H16B 109.5 ?
C15A C16A H16C 109.5 ?
H16A C16A H16C 109.5 ?
H16B C16A H16C 109.5 ?
O5 C15B C16B 109.2(11) ?
O5 C15B H15C 109.8 ?
C16B C15B H15C 109.8 ?
O5 C15B H15D 109.8 ?
C16B C15B H15D 109.8 ?
H15C C15B H15D 108.3 ?
C15B C16B H16D 109.5 ?
C15B C16B H16E 109.5 ?
H16D C16B H16E 109.5 ?
C15B C16B H16F 109.5 ?
H16D C16B H16F 109.5 ?
H16E C16B H16F 109.5 ?
C18 C17 C9 128.1(2) ?
C18 C17 S1 110.2(2) ?
C9 C17 S1 121.57(18) yes
C17 C18 C19 112.4(3) ?
C17 C18 H18A 123.8 ?
C19 C18 H18A 123.8 ?
C20 C19 C18 113.6(3) ?
C20 C19 H19A 123.2 ?
C18 C19 H19A 123.2 ?
C19 C20 S1 111.4(2) ?
C19 C20 H20B 124.3 ?
S1 C20 H20B 124.3 ?
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 C20 . 1.704(3) yes
S1 C17 . 1.724(2) yes
F1 C3 . 1.361(3) yes
O1 C7 . 1.213(3) yes
O2 C11 . 1.315(3) yes
O2 C12 . 1.465(3) yes
O3 C11 . 1.194(3) yes
O4 C14 . 1.201(3) yes
O5 C14 . 1.318(3) yes
O5 C15B . 1.471(10) no
O5 C15A . 1.540(12) no
N1 C7 . 1.372(3) yes
N1 C6 . 1.442(3) yes
N1 C10 . 1.471(3) yes
C1 C6 . 1.370(4) ?
C1 C2 . 1.390(4) ?
C1 H1A . .9300 ?
C2 C3 . 1.354(5) ?
C2 H2A . .9300 ?
C3 C4 . 1.366(5) ?
C4 C5 . 1.379(4) ?
C4 H4A . .9300 ?
C5 C6 . 1.379(4) ?
C5 H5A . .9300 ?
C7 C8 . 1.503(4) yes
C8 C9 . 1.533(3) yes
C8 H8A . .9700 ?
C8 H8B . .9700 ?
C9 C17 . 1.497(3) yes
C9 C10 . 1.573(3) yes
C9 H9A . .9800 ?
C10 C11 . 1.531(3) yes
C10 C14 . 1.532(4) ?
C12 C13 . 1.453(5) ?
C12 H12A . .9700 ?
C12 H12B . .9700 ?
C13 H13A . .9600 ?
C13 H13B . .9600 ?
C13 H13C . .9600 ?
C15A C16A . 1.49(3) no
C15A H15A . .9700 ?
C15A H15B . .9700 ?
C16A H16A . .9600 ?
C16A H16B . .9600 ?
C16A H16C . .9600 ?
C15B C16B . 1.49(2) no
C15B H15C . .9700 ?
C15B H15D . .9700 ?
C16B H16D . .9600 ?
C16B H16E . .9600 ?
C16B H16F . .9600 ?
C17 C18 . 1.369(4) yes
C18 C19 . 1.419(4) yes
C18 H18A . .9300 ?
C19 C20 . 1.337(5) yes
C19 H19A . .9300 ?
C20 H20B . .9300 ?
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
_geom_hbond_publ_flag
C8 H8A O4 2_556 .9692 2.5428 3.415(4) 150 yes
C9 H9A O2 1_555 .9807 2.3605 2.718(3) 100 yes
C12 H12B O3 2_455 .9698 2.5875 3.443(5) 147 yes
C18 H18A O4 2_556 .9308 2.5744 3.496(5) 171 yes
C20 H20B O1 1_665 .9293 2.4672 3.327(4) 154 yes
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
C6 C1 C2 C3 -1.4(5) ?
C1 C2 C3 F1 -179.7(3) ?
C1 C2 C3 C4 1.4(5) ?
C2 C3 C4 C5 -.6(5) ?
F1 C3 C4 C5 -179.6(3) ?
C3 C4 C5 C6 -.1(5) ?
C2 C1 C6 C5 .8(4) ?
C2 C1 C6 N1 177.7(3) ?
C4 C5 C6 C1 .0(4) ?
C4 C5 C6 N1 -177.0(2) ?
C7 N1 C6 C1 -98.2(3) ?
C10 N1 C6 C1 76.1(3) ?
C7 N1 C6 C5 78.8(3) ?
C10 N1 C6 C5 -106.9(3) ?
C6 N1 C7 O1 1.2(4) ?
C10 N1 C7 O1 -173.8(2) ?
C6 N1 C7 C8 -179.8(2) ?
C10 N1 C7 C8 5.2(3) ?
O1 C7 C8 C9 -165.2(3) ?
N1 C7 C8 C9 15.9(3) ?
C7 C8 C9 C17 -156.9(2) ?
C7 C8 C9 C10 -28.8(3) ?
C7 N1 C10 C11 -145.9(2) ?
C6 N1 C10 C11 39.4(3) ?
C7 N1 C10 C14 93.1(2) ?
C6 N1 C10 C14 -81.6(3) ?
C7 N1 C10 C9 -23.1(2) ?
C6 N1 C10 C9 162.1(2) ?
C17 C9 C10 N1 156.56(19) ?
C8 C9 C10 N1 30.8(2) ?
C17 C9 C10 C11 -84.1(3) ?
C8 C9 C10 C11 150.1(2) ?
C17 C9 C10 C14 39.1(3) ?
C8 C9 C10 C14 -86.7(2) ?
C12 O2 C11 O3 -4.7(4) ?
C12 O2 C11 C10 175.9(2) yes
N1 C10 C11 O3 -67.4(3) ?
C14 C10 C11 O3 55.0(3) ?
C9 C10 C11 O3 178.6(3) ?
N1 C10 C11 O2 111.9(2) ?
C14 C10 C11 O2 -125.6(2) ?
C9 C10 C11 O2 -2.0(3) ?
C11 O2 C12 C13 176.2(3) ?
C15B O5 C14 O4 6.1(9) ?
C15A O5 C14 O4 -14.8(7) ?
C15B O5 C14 C10 -178.0(8) no
C15A O5 C14 C10 161.1(7) no
N1 C10 C14 O4 -21.4(3) ?
C11 C10 C14 O4 -143.4(3) ?
C9 C10 C14 O4 89.5(3) ?
N1 C10 C14 O5 162.6(2) ?
C11 C10 C14 O5 40.6(3) ?
C9 C10 C14 O5 -86.5(2) ?
C14 O5 C15A C16A -167.8(16) ?
C15B O5 C15A C16A 49.2(19) ?
C14 O5 C15B C16B -104.2(13) ?
C15A O5 C15B C16B -57.5(19) ?
C8 C9 C17 C18 12.7(4) ?
C10 C9 C17 C18 -107.4(3) ?
C8 C9 C17 S1 -161.93(19) ?
C10 C9 C17 S1 78.0(2) ?
C20 S1 C17 C18 -.2(2) ?
C20 S1 C17 C9 175.3(2) ?
C9 C17 C18 C19 -175.0(3) ?
S1 C17 C18 C19 .2(3) ?
C17 C18 C19 C20 .0(4) ?
C18 C19 C20 S1 -.2(4) ?
C17 S1 C20 C19 .3(3) ?
