data_2013822
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2004
_journal_volume  60
_journal_page_first  o163
_journal_page_last  o165
_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
;
loop_
_publ_author_name
  'Ray, Jayanta Kumar'
  'Haldar, Pranab'
  'Canle L., M.'
  'Santaballa, J. A.'
  'Mah\'ia, Jose'
_chemical_formula_moiety  'C20 H19 Cl2 N O6'
_chemical_formula_sum  'C20 H19 Cl2 N O6'
_chemical_formula_iupac  'C20 H19 Cl2 N O6'
_chemical_formula_weight  440.26
_chemical_melting_point  .353E-305
_symmetry_cell_setting  Triclinic
_symmetry_space_group_name_H-M  'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  9.5478(9)
_cell_length_b  10.2319(9)
_cell_length_c  12.5088(11)
_cell_angle_alpha  72.749(2)
_cell_angle_beta  86.206(2)
_cell_angle_gamma  64.310(2)
_cell_volume  1048.91(16)
_cell_formula_units_Z  2
_cell_measurement_temperature  298(2)
_exptl_crystal_density_diffrn  1.394
_diffrn_ambient_temperature  298(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_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
  Cl1 0.48018(8) 0.71104(8) 0.48180(6) 0.0648(2) Uani d . 1 . . Cl
  Cl2 0.19057(11) 1.02484(10) 0.46814(8) 0.0985(4) Uani d . 1 . . Cl
  O1 0.1938(2) 0.87834(19) 0.00114(14) 0.0600(5) Uani d . 1 . . O
  O2 0.1639(2) 0.2812(2) 0.10045(16) 0.0604(5) Uani d . 1 . . O
  O3 0.50154(19) 0.4559(2) 0.17934(16) 0.0586(5) Uani d . 1 . . O
  O4 0.41958(18) 0.27495(18) 0.24500(14) 0.0527(4) Uani d . 1 . . O
  O5 0.1940(2) 0.4423(3) 0.37959(15) 0.0745(6) Uani d . 1 . . O
  O6 -0.0102(2) 0.5385(3) 0.25919(17) 0.0870(7) Uani d . 1 . . O
  N1 0.2024(2) 0.6852(2) 0.15596(14) 0.0417(4) Uani d . 1 . . N
  C1 0.1971(3) 0.7538(3) 0.04250(18) 0.0452(5) Uani d . 1 . . C
  C2 0.1988(3) 0.6467(3) -0.01788(18) 0.0473(5) Uani d . 1 . . C
  H2A 0.3002 0.5995 -0.0456 0.057 Uiso calc R 1 . . H
  H2B 0.1207 0.6996 -0.0807 0.057 Uiso calc R 1 . . H
  C3 0.1620(3) 0.5280(3) 0.06979(18) 0.0424(5) Uani d . 1 . . C
  H3A 0.0484 0.5675 0.0703 0.051 Uiso calc R 1 . . H
  C4 0.2253(2) 0.5273(2) 0.18339(17) 0.0391(5) Uani d . 1 . . C
  C5 0.2003(3) 0.7609(2) 0.23584(18) 0.0420(5) Uani d . 1 . . C
  C6 0.3258(3) 0.7050(3) 0.31264(19) 0.0455(5) Uani d . 1 . . C
  H6A 0.4123 0.6146 0.3147 0.055 Uiso calc R 1 . . H
  C7 0.3223(3) 0.7839(3) 0.38608(19) 0.0477(5) Uani d . 1 . . C
  C8 0.1948(3) 0.9202(3) 0.3808(2) 0.0581(6) Uani d . 1 . . C
  C9 0.0694(3) 0.9747(3) 0.3046(2) 0.0654(7) Uani d . 1 . . C
  H9A -0.0165 1.0659 0.3017 0.078 Uiso calc R 1 . . H
  C10 0.0710(3) 0.8947(3) 0.2329(2) 0.0546(6) Uani d . 1 . . C
  H10A -0.0145 0.9306 0.1828 0.066 Uiso calc R 1 . . H
  C11 0.2222(3) 0.3815(3) 0.04416(19) 0.0455(5) Uani d . 1 . . C
  C12 0.3202(3) 0.3247(3) -0.0289(2) 0.0639(7) Uani d . 1 . . C
  H12A 0.3757 0.3703 -0.0769 0.077 Uiso calc R 1 . . H
  C13 0.3237(4) 0.1821(3) -0.0198(3) 0.0783(9) Uani d . 1 . . C
  H13A 0.3814 0.1163 -0.0609 0.094 Uiso calc R 1 . . H
  C14 0.2296(4) 0.1605(3) 0.0579(3) 0.0748(9) Uani d . 1 . . C
  H14A 0.2103 0.0751 0.0809 0.090 Uiso calc R 1 . . H
  C15 0.3991(3) 0.4169(3) 0.20421(18) 0.0424(5) Uani d . 1 . . C
  C16 0.5786(3) 0.1584(3) 0.2504(3) 0.0682(7) Uani d . 1 . . C
  H16A 0.6463 0.1679 0.2991 0.082 Uiso calc R 1 . . H
  H16B 0.6175 0.1696 0.1762 0.082 Uiso calc R 1 . . H
  C17 0.5761(4) 0.0088(4) 0.2949(4) 0.0978(12) Uani d . 1 . . C
  H17A 0.6797 -0.0701 0.2992 0.147 Uiso calc R 1 . . H
  H17B 0.5091 0.0004 0.2459 0.147 Uiso calc R 1 . . H
  H17C 0.5378 -0.0013 0.3684 0.147 Uiso calc R 1 . . H
  C18 0.1366(3) 0.4932(3) 0.28685(19) 0.0456(5) Uani d . 1 . . C
  C19 -0.1125(5) 0.5277(7) 0.3508(4) 0.131(2) Uani d . 1 . . C
  H19A -0.0538 0.4939 0.4220 0.158 Uiso calc R 1 . . H
  H19B -0.1969 0.6275 0.3434 0.158 Uiso calc R 1 . . H
  C20 -0.1741(6) 0.4272(6) 0.3504(5) 0.142(2) Uani d . 1 . . C
  H20A -0.2565 0.4387 0.4004 0.213 Uiso calc R 1 . . H
  H20B -0.0938 0.3250 0.3748 0.213 Uiso calc R 1 . . H
  H20C -0.2145 0.4485 0.2758 0.213 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
  Cl1 0.0686(4) 0.0664(4) 0.0601(4) -0.0267(3) -0.0157(3) -0.0195(3)
  Cl2 0.1109(7) 0.0846(6) 0.0944(6) -0.0125(5) -0.0190(5) -0.0597(5)
  O1 0.0856(13) 0.0478(10) 0.0493(10) -0.0353(9) 0.0058(9) -0.0084(8)
  O2 0.0650(11) 0.0591(11) 0.0696(12) -0.0392(9) 0.0051(9) -0.0175(9)
  O3 0.0453(9) 0.0632(11) 0.0779(12) -0.0306(8) 0.0167(8) -0.0274(9)
  O4 0.0488(9) 0.0462(9) 0.0588(10) -0.0202(7) -0.0017(7) -0.0092(8)
  O5 0.0713(12) 0.1050(16) 0.0385(10) -0.0395(11) 0.0077(9) -0.0084(10)
  O6 0.0581(12) 0.170(2) 0.0598(12) -0.0676(14) 0.0266(9) -0.0485(14)
  N1 0.0486(10) 0.0433(10) 0.0365(9) -0.0233(8) 0.0015(8) -0.0110(8)
  C1 0.0480(12) 0.0472(13) 0.0402(12) -0.0224(10) 0.0039(9) -0.0101(10)
  C2 0.0562(13) 0.0536(13) 0.0376(12) -0.0293(11) 0.0048(10) -0.0133(10)
  C3 0.0418(11) 0.0517(13) 0.0395(11) -0.0249(10) 0.0020(9) -0.0143(10)
  C4 0.0410(11) 0.0448(12) 0.0372(11) -0.0240(9) 0.0039(8) -0.0120(9)
  C5 0.0457(12) 0.0442(12) 0.0380(11) -0.0215(10) 0.0044(9) -0.0121(9)
  C6 0.0474(12) 0.0422(12) 0.0458(12) -0.0177(10) 0.0001(10) -0.0135(10)
  C7 0.0531(13) 0.0482(13) 0.0428(12) -0.0238(11) -0.0034(10) -0.0105(10)
  C8 0.0696(16) 0.0563(15) 0.0513(14) -0.0228(13) 0.0007(12) -0.0262(12)
  C9 0.0614(16) 0.0567(15) 0.0630(17) -0.0042(12) -0.0040(13) -0.0286(13)
  C10 0.0484(13) 0.0576(15) 0.0505(14) -0.0146(11) -0.0028(10) -0.0176(11)
  C11 0.0506(13) 0.0511(13) 0.0427(12) -0.0290(11) -0.0011(10) -0.0134(10)
  C12 0.0799(19) 0.0614(16) 0.0566(16) -0.0338(14) 0.0147(14) -0.0234(13)
  C13 0.103(2) 0.0608(18) 0.071(2) -0.0278(17) 0.0056(18) -0.0316(15)
  C14 0.095(2) 0.0506(16) 0.087(2) -0.0379(16) -0.0075(18) -0.0202(15)
  C15 0.0461(12) 0.0487(13) 0.0378(11) -0.0239(10) 0.0038(9) -0.0154(9)
  C16 0.0575(16) 0.0576(16) 0.0765(19) -0.0138(13) -0.0015(14) -0.0181(14)
  C17 0.094(2) 0.0527(18) 0.133(3) -0.0200(17) -0.013(2) -0.0218(19)
  C18 0.0499(13) 0.0536(13) 0.0423(13) -0.0306(11) 0.0106(10) -0.0157(10)
  C19 0.111(3) 0.269(6) 0.102(3) -0.136(4) 0.074(3) -0.107(4)
  C20 0.167(5) 0.142(4) 0.153(4) -0.104(4) 0.095(4) -0.053(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
  Cl1 C7 . 1.731(2) ?
  Cl2 C8 . 1.729(2) ?
  O1 C1 . 1.212(3) ?
  O2 C11 . 1.368(3) ?
  O2 C14 . 1.370(3) ?
  O3 C15 . 1.199(3) ?
  O4 C15 . 1.317(3) ?
  O4 C16 . 1.459(3) ?
  O5 C18 . 1.181(3) ?
  O6 C18 . 1.306(3) ?
  O6 C19 . 1.466(4) ?
  N1 C1 . 1.378(3) ?
  N1 C5 . 1.429(3) ?
  N1 C4 . 1.466(3) ?
  C1 C2 . 1.499(3) ?
  C2 C3 . 1.526(3) ?
  C2 H2A . 0.9700 ?
  C2 H2B . 0.9700 ?
  C3 C11 . 1.481(3) ?
  C3 C4 . 1.577(3) ?
  C3 H3A . 0.9800 ?
  C4 C15 . 1.535(3) ?
  C4 C18 . 1.535(3) ?
  C5 C10 . 1.383(3) ?
  C5 C6 . 1.385(3) ?
  C6 C7 . 1.381(3) ?
  C6 H6A . 0.9300 ?
  C7 C8 . 1.384(3) yes
  C8 C9 . 1.382(4) yes
  C9 C10 . 1.377(3) ?
  C9 H9A . 0.9300 ?
  C10 H10A . 0.9300 ?
  C11 C12 . 1.334(4) yes
  C12 C13 . 1.416(4) ?
  C12 H12A . 0.9300 ?
  C13 C14 . 1.316(5) yes
  C13 H13A . 0.9300 ?
  C14 H14A . 0.9300 ?
  C16 C17 . 1.476(4) ?
  C16 H16A . 0.9700 ?
  C16 H16B . 0.9700 ?
  C17 H17A . 0.9600 ?
  C17 H17B . 0.9600 ?
  C17 H17C . 0.9600 ?
  C19 C20 . 1.390(6) yes
  C19 H19A . 0.9700 ?
  C19 H19B . 0.9700 ?
  C20 H20A . 0.9600 ?
  C20 H20B . 0.9600 ?
  C20 H20C . 0.9600 ?