#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/38/2013821.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_2013821
loop_
_publ_author_name
'Ray, Jayanta Kumar'
'Haldar, Pranab'
'Canle L., M.'
'Santaballa, J. A.'
'Mahía, Jose'
_publ_section_title
;
 Diethyl
 1-(4-fluorophenyl)-3-(2-furyl)-5-oxopyrrolidine-2,2-dicarboxylate and
 diethyl
 1-(3,4-dichlorophenyl)-3-(2-furyl)-5-oxopyrrolidine-2,2-dicarboxylate
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o163
_journal_page_last               o165
_journal_paper_doi               10.1107/S0108270103029111
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C20 H20 F N O6'
_chemical_formula_moiety         'C20 H20 F N O6'
_chemical_formula_sum            'C20 H20 F N O6'
_chemical_formula_weight         389.37
_chemical_melting_point          .355E-305
_chemical_name_systematic
;
Diethyl 1-(4-fluorophenyl)-3-(2-furyl)-5-oxopyrrolidine -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                90.305(6)
_cell_angle_beta                 105.358(6)
_cell_angle_gamma                112.405(5)
_cell_formula_units_Z            2
_cell_length_a                   9.582(3)
_cell_length_b                   10.157(3)
_cell_length_c                   11.384(4)
_cell_measurement_reflns_used    2470
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.0
_cell_volume                     980.7(5)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0145
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6019
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.18
_diffrn_standards_decay_%        0.51
_diffrn_standards_interval_count 'set of frames'
_diffrn_standards_number         '50 first frames'
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9775
_exptl_absorpt_correction_T_min  0.8853
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.253
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4167
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0644P)²+0.1569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1297
_reflns_number_gt                2936
_reflns_number_total             4167
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na1631.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_original_cell_volume        980.6(5)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2013821
_cod_database_fobs_code          2013821
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
F1 0.4839(2) 1.69158(16) 0.20331(17) 0.1212(7) Uani d . 1 . . F
O1 -0.12609(16) 1.21079(14) 0.23505(15) 0.0643(4) Uani d . 1 . . O
O2 -0.03167(19) 0.66550(14) 0.19518(14) 0.0675(4) Uani d . 1 . . O
O3 0.19164(17) 1.07698(14) 0.46584(11) 0.0557(4) Uani d . 1 . . O
O4 0.25249(14) 0.90995(13) 0.38829(10) 0.0454(3) Uani d . 1 . . O
O5 0.15804(16) 0.95687(17) 0.05851(12) 0.0655(4) Uani d . 1 . . O
O6 0.36412(14) 1.08679(15) 0.21550(11) 0.0539(3) Uani d . 1 . . O
N1 0.07687(15) 1.14449(13) 0.23426(12) 0.0355(3) Uani d . 1 . . N
C1 -0.0740(2) 1.11918(18) 0.23530(16) 0.0420(4) Uani d . 1 . . C
C2 -0.1583(2) 0.96201(17) 0.24003(17) 0.0436(4) Uani d . 1 . . C
H2A -0.2632 0.9252 0.1825 0.052 Uiso calc R 1 . . H
H2B -0.1671 0.9436 0.3219 0.052 Uiso calc R 1 . . H
C3 -0.05662(18) 0.89350(16) 0.20475(15) 0.0360(4) Uani d . 1 . . C
H3A -0.0886 0.8751 0.1150 0.043 Uiso calc R 1 . . H
C4 0.11306(17) 1.01679(16) 0.24659(13) 0.0324(3) Uani d . 1 . . C
C5 0.18628(19) 1.28553(16) 0.22720(15) 0.0382(4) Uani d . 1 . . C
C6 0.3174(2) 1.35984(19) 0.32375(18) 0.0533(5) Uani d . 1 . . C
H6A 0.3374 1.3182 0.3955 0.064 Uiso calc R 1 . . H
C7 0.4195(3) 1.4963(2) 0.3143(2) 0.0683(6) Uani d . 1 . . C
H7A 0.5099 1.5463 0.3783 0.082 Uiso calc R 1 . . H
C8 0.3852(3) 1.5555(2) 0.2103(2) 0.0751(7) Uani d . 1 . . C
C9 0.2567(3) 1.4849(2) 0.1131(2) 0.0812(7) Uani d . 1 . . C
H9A 0.2367 1.5284 0.0425 0.097 Uiso calc R 1 . . H
C10 0.1561(2) 1.3470(2) 0.12134(18) 0.0572(5) Uani d . 1 . . C
H10A 0.0686 1.2962 0.0555 0.069 Uiso calc R 1 . . H
C11 -0.0740(2) 0.75493(17) 0.25436(17) 0.0436(4) Uani d . 1 . . C
C12 -0.1202(3) 0.6984(2) 0.3499(2) 0.0684(6) Uani d . 1 . . C
H12A -0.1533 0.7387 0.4052 0.082 Uiso calc R 1 . . H
C13 -0.1077(3) 0.5610(3) 0.3490(3) 0.0880(9) Uani d . 1 . . C
H13A -0.1325 0.4943 0.4039 0.106 Uiso calc R 1 . . H
C14 -0.0549(3) 0.5479(2) 0.2565(3) 0.0841(8) Uani d . 1 . . C
H14A -0.0359 0.4690 0.2356 0.101 Uiso calc R 1 . . H
C15 0.19318(18) 1.00859(17) 0.38058(14) 0.0367(4) Uani d . 1 . . C
C16 0.3037(2) 0.8702(2) 0.51026(17) 0.0565(5) Uani d . 1 . . C
H16A 0.2171 0.8367 0.5464 0.068 Uiso calc R 1 . . H
H16B 0.3891 0.9520 0.5635 0.068 Uiso calc R 1 . . H
C17 0.3578(3) 0.7535(2) 0.4944(2) 0.0700(6) Uani d . 1 . . C
H17A 0.3897 0.7219 0.5725 0.105 Uiso calc R 1 . . H
H17B 0.4455 0.7889 0.4608 0.105 Uiso calc R 1 . . H
H17C 0.2732 0.6745 0.4395 0.105 Uiso calc R 1 . . H
C18 0.21248(19) 1.01333(18) 0.16132(15) 0.0382(4) Uani d . 1 . . C
C19 0.4739(3) 1.1002(3) 0.1436(2) 0.0738(7) Uani d . 1 . . C
H19A 0.5700 1.0964 0.1959 0.089 Uiso calc R 1 . . H
H19B 0.4271 1.0208 0.0786 0.089 Uiso calc R 1 . . H
C20 0.5115(3) 1.2358(3) 0.0902(3) 0.0996(9) Uani d . 1 . . C
H20A 0.5834 1.2431 0.0433 0.149 Uiso calc R 1 . . H
H20B 0.5592 1.3143 0.1547 0.149 Uiso calc R 1 . . H
H20C 0.4165 1.2390 0.0377 0.149 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'
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
C14 O2 C11 106.14(19) ?
C15 O4 C16 116.77(13) ?
C18 O6 C19 117.65(15) ?
C1 N1 C5 121.46(13) ?
C1 N1 C4 113.29(12) ?
C5 N1 C4 125.19(12) ?
O1 C1 N1 124.72(15) ?
O1 C1 C2 127.00(15) ?
N1 C1 C2 108.26(13) ?
C1 C2 C3 104.66(13) ?
C1 C2 H2A 110.8 ?
C3 C2 H2A 110.8 ?
C1 C2 H2B 110.8 ?
C3 C2 H2B 110.8 ?
H2A C2 H2B 108.9 ?
C11 C3 C2 113.57(13) ?
C11 C3 C4 116.31(13) ?
C2 C3 C4 103.10(12) ?
C11 C3 H3A 107.8 ?
C2 C3 H3A 107.8 ?
C4 C3 H3A 107.8 ?
N1 C4 C15 111.45(12) ?
N1 C4 C18 109.80(12) ?
C15 C4 C18 112.26(13) ?
N1 C4 C3 101.46(12) yes
C15 C4 C3 109.18(12) ?
C18 C4 C3 112.22(13) ?
C10 C5 C6 120.04(16) ?
C10 C5 N1 118.30(15) ?
C6 C5 N1 121.65(15) ?
C5 C6 C7 120.14(18) ?
C5 C6 H6A 119.9 ?
C7 C6 H6A 119.9 ?
C8 C7 C6 118.61(19) ?
C8 C7 H7A 120.7 ?
C6 C7 H7A 120.7 ?
C7 C8 C9 122.71(19) ?
C7 C8 F1 118.2(2) ?
C9 C8 F1 119.1(2) ?
C8 C9 C10 118.7(2) ?
C8 C9 H9A 120.6 ?
C10 C9 H9A 120.6 ?
C5 C10 C9 119.75(18) ?
C5 C10 H10A 120.1 ?
C9 C10 H10A 120.1 ?
C12 C11 O2 110.88(17) ?
C12 C11 C3 132.82(17) ?
O2 C11 C3 116.28(15) ?
C11 C12 C13 105.0(2) ?
C11 C12 H12A 127.5 ?
C13 C12 H12A 127.5 ?
C14 C13 C12 107.2(2) ?
C14 C13 H13A 126.4 ?
C12 C13 H13A 126.4 ?
C13 C14 O2 110.8(2) ?
C13 C14 H14A 124.6 ?
O2 C14 H14A 124.6 ?
O3 C15 O4 125.43(15) ?
O3 C15 C4 123.41(15) ?
O4 C15 C4 110.99(13) ?
O4 C16 C17 106.70(16) ?
O4 C16 H16A 110.4 ?
C17 C16 H16A 110.4 ?
O4 C16 H16B 110.4 ?
C17 C16 H16B 110.4 ?
H16A C16 H16B 108.6 ?
C16 C17 H17A 109.5 ?
C16 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
C16 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
O5 C18 O6 125.00(15) ?
O5 C18 C4 123.86(15) ?
O6 C18 C4 111.06(14) ?
C20 C19 O6 110.4(2) ?
C20 C19 H19A 109.6 ?
O6 C19 H19A 109.6 ?
C20 C19 H19B 109.6 ?
O6 C19 H19B 109.6 ?
H19A C19 H19B 108.1 ?
C19 C20 H20A 109.5 ?
C19 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
C19 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
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
F1 C8 . 1.362(2) ?
O1 C1 . 1.2120(19) ?
O2 C14 . 1.361(3) ?
O2 C11 . 1.365(2) ?
O3 C15 . 1.1970(19) ?
O4 C15 . 1.3203(19) ?
O4 C16 . 1.459(2) ?
O5 C18 . 1.188(2) ?
O6 C18 . 1.320(2) ?
O6 C19 . 1.464(2) ?
N1 C1 . 1.371(2) ?
N1 C5 . 1.435(2) ?
N1 C4 . 1.4635(19) ?
C1 C2 . 1.498(2) ?
C2 C3 . 1.522(2) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C11 . 1.486(2) ?
C3 C4 . 1.572(2) ?
C3 H3A . 0.9800 ?
C4 C15 . 1.534(2) ?
C4 C18 . 1.538(2) ?
C5 C10 . 1.373(2) ?
C5 C6 . 1.376(2) ?
C6 C7 . 1.383(3) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.351(3) yes
C7 H7A . 0.9300 ?
C8 C9 . 1.361(3) yes
C9 C10 . 1.386(3) ?
C9 H9A . 0.9300 ?
C10 H10A . 0.9300 ?
C11 C12 . 1.333(3) yes
C12 C13 . 1.446(3) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.309(4) yes
C13 H13A . 0.9300 ?
C14 H14A . 0.9300 ?
C16 C17 . 1.491(3) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C19 C20 . 1.463(4) yes
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
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
C2 H2B O3 2_576 0.97 2.49 3.457(2) 174
C14 H14A O1 1_545 0.93 2.43 3.220(3) 143
C19 H19A O1 1_655 0.97 2.60 3.410(3) 141
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
C5 N1 C1 O1 -2.8(3) ?
C4 N1 C1 O1 174.55(17) ?
C5 N1 C1 C2 178.61(14) ?
C4 N1 C1 C2 -4.03(19) ?
O1 C1 C2 C3 165.64(18) ?
N1 C1 C2 C3 -15.83(19) ?
C1 C2 C3 C11 154.40(15) ?
C1 C2 C3 C4 27.67(16) ?
C1 N1 C4 C15 -94.87(16) ?
C5 N1 C4 C15 82.38(17) ?
C1 N1 C4 C18 140.10(14) ?
C5 N1 C4 C18 -42.65(19) ?
C1 N1 C4 C3 21.22(16) ?
C5 N1 C4 C3 -161.53(14) ?
C11 C3 C4 N1 -154.13(13) ?
C2 C3 C4 N1 -29.15(14) ?
C11 C3 C4 C15 -36.38(17) ?
C2 C3 C4 C15 88.60(14) ?
C11 C3 C4 C18 88.74(16) ?
C2 C3 C4 C18 -146.29(13) ?
C1 N1 C5 C10 -66.6(2) yes
C4 N1 C5 C10 116.36(18) ?
C1 N1 C5 C6 112.42(19) ?
C4 N1 C5 C6 -64.6(2) ?
C10 C5 C6 C7 -0.3(3) ?
N1 C5 C6 C7 -179.27(18) ?
C5 C6 C7 C8 1.7(3) ?
C6 C7 C8 C9 -1.8(4) ?
C6 C7 C8 F1 178.0(2) ?
C7 C8 C9 C10 0.4(4) ?
F1 C8 C9 C10 -179.4(2) ?
C6 C5 C10 C9 -1.2(3) ?
N1 C5 C10 C9 177.9(2) ?
C8 C9 C10 C5 1.1(4) ?
C14 O2 C11 C12 0.8(2) ?
C14 O2 C11 C3 179.16(17) ?
C2 C3 C11 C12 -23.6(3) ?
C4 C3 C11 C12 95.8(2) ?
C2 C3 C11 O2 158.45(15) ?
C4 C3 C11 O2 -82.10(19) ?
O2 C11 C12 C13 -0.9(2) ?
C3 C11 C12 C13 -178.9(2) ?
C11 C12 C13 C14 0.7(3) ?
C12 C13 C14 O2 -0.2(3) ?
C11 O2 C14 C13 -0.3(3) ?
C16 O4 C15 O3 7.4(2) ?
C16 O4 C15 C4 -167.98(14) yes
N1 C4 C15 O3 16.6(2) ?
C18 C4 C15 O3 140.26(16) ?
C3 C4 C15 O3 -94.65(18) ?
N1 C4 C15 O4 -167.88(12) ?
C18 C4 C15 O4 -44.24(17) ?
C3 C4 C15 O4 80.85(15) ?
C15 O4 C16 C17 177.24(15) yes
C19 O6 C18 O5 0.2(3) ?
C19 O6 C18 C4 -176.75(16) yes
N1 C4 C18 O5 -90.32(19) ?
C15 C4 C18 O5 145.12(17) ?
C3 C4 C18 O5 21.7(2) ?
N1 C4 C18 O6 86.63(16) ?
C15 C4 C18 O6 -37.93(18) ?
C3 C4 C18 O6 -161.33(13) ?
C18 O6 C19 C20 96.1(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4414790
