#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202607.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2202607
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o1002
_journal_page_last  o1003
_publ_section_title
;
8,8'-Dichloro-1,1',5,5'-tetrahydro-10,10'-bipyrrolo[1,2-b]isoquinoline-
3,3'(2H,2'H)-dione
;
loop_
_publ_author_name
  'Camus, Fabrice'
  'Norberg, Bernadette'
  'Bourry, Anne'
  'Aku\'e-G\'edu, Rufine'
  'Rigo, Beno\^it'
  'Durant, Fran\,cois'
_chemical_formula_moiety  'C24 H18 Cl2 N2 O2'
_chemical_formula_sum  'C24 H18 Cl2 N2 O2'
_chemical_formula_iupac  'C24 H18 Cl2 N2 O2'
_chemical_formula_weight  437.30
_symmetry_cell_setting  'monoclinic'
_symmetry_space_group_name_H-M  'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y-1/2, z-1/2'
_cell_length_a  8.1130(10)
_cell_length_b  12.0890(10)
_cell_length_c  20.181(2)
_cell_angle_alpha  90.00
_cell_angle_beta  92.79(3)
_cell_angle_gamma  90.00
_cell_volume  1977.0(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.469
_diffrn_ambient_temperature  293(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
  Cl34 0.38303(10) 0.75010(6) -0.13875(3) 0.0821(3) Uani d . 1 . . Cl
  Cl14 -0.37369(10) 0.64263(7) 0.02067(4) 0.0923(3) Uani d . 1 . . Cl
  O15 0.5730(3) 0.4899(2) 0.22826(13) 0.1124(8) Uani d . 1 . . O
  O35 0.0581(3) 1.20184(14) 0.16812(10) 0.0787(5) Uani d . 1 . . O
  N26 0.1280(2) 1.03773(13) 0.12151(9) 0.0501(4) Uani d . 1 . . N
  N6 0.3809(3) 0.59217(15) 0.16983(10) 0.0641(5) Uani d . 1 . . N
  C31 0.1943(3) 0.85067(15) 0.09537(10) 0.0467(5) Uani d . 1 . . C
  C13 -0.0627(3) 0.67889(18) 0.06927(11) 0.0573(6) Uani d . 1 . . C
  H13 -0.0828 0.7525 0.0582 0.069 Uiso calc R 1 . . H
  C10 0.3516(3) 0.70229(17) 0.15084(11) 0.0548(5) Uani d . 1 . . C
  C29 0.0640(4) 0.9102(2) 0.20386(12) 0.0676(6) Uani d . 1 . . C
  H29A 0.1472 0.8824 0.2358 0.081 Uiso calc R 1 . . H
  H29B -0.0281 0.8590 0.2013 0.081 Uiso calc R 1 . . H
  C30 0.1345(3) 0.92567(16) 0.13695(10) 0.0486(5) Uani d . 1 . . C
  C33 0.2857(3) 0.81184(17) -0.01868(11) 0.0518(5) Uani d . 1 . . C
  H33 0.2830 0.7365 -0.0096 0.062 Uiso calc R 1 . . H
  C21 0.3318(3) 0.84755(18) -0.07967(11) 0.0564(5) Uani d . 1 . . C
  C12 0.0885(3) 0.64865(16) 0.09836(10) 0.0523(5) Uani d . 1 . . C
  C32 0.2430(2) 0.88740(15) 0.02971(10) 0.0454(4) Uani d . 1 . . C
  C11 0.2164(3) 0.73258(16) 0.11550(11) 0.0506(5) Uani d . 1 . . C
  C23 0.2956(3) 1.03369(18) -0.04684(12) 0.0582(6) Uani d . 1 . . C
  H23 0.2997 1.1089 -0.0564 0.070 Uiso calc R 1 . . H
  C9 0.4932(3) 0.7706(2) 0.17792(13) 0.0671(6) Uani d . 1 . . C
  H9A 0.4555 0.8264 0.2082 0.081 Uiso calc R 1 . . H
  H9B 0.5485 0.8069 0.1423 0.081 Uiso calc R 1 . . H
  C28 0.0071(4) 1.0261(2) 0.22320(13) 0.0738(7) Uani d . 1 . . C
  H28A -0.1120 1.0286 0.2252 0.089 Uiso calc R 1 . . H
  H28B 0.0562 1.0472 0.2661 0.089 Uiso calc R 1 . . H
  C8 0.6083(4) 0.6891(3) 0.21414(14) 0.0778(8) Uani d . 1 . . C
  H8A 0.7150 0.6878 0.1945 0.093 Uiso calc R 1 . . H
  H8B 0.6238 0.7088 0.2606 0.093 Uiso calc R 1 . . H
  C4 0.1176(3) 0.53706(17) 0.11382(12) 0.0614(6) Uani d . 1 . . C
  C24 0.2457(3) 1.00078(16) 0.01429(10) 0.0479(5) Uani d . 1 . . C
  C1 -0.1836(3) 0.6009(2) 0.05652(13) 0.0657(6) Uani d . 1 . . C
  C3 -0.0082(4) 0.46050(18) 0.10093(14) 0.0756(8) Uani d . 1 . . C
  H3 0.0100 0.3866 0.1117 0.091 Uiso calc R 1 . . H
  C25 0.2023(3) 1.08603(17) 0.06466(13) 0.0627(6) Uani d . 1 . . C
  H25A 0.3014 1.1256 0.0794 0.075 Uiso calc R 1 . . H
  H25B 0.1262 1.1391 0.0440 0.075 Uiso calc R 1 . . H
  C2 -0.1591(4) 0.4919(2) 0.07247(14) 0.0766(8) Uani d . 1 . . C
  H2 -0.2424 0.4401 0.0643 0.092 Uiso calc R 1 . . H
  C22 0.3397(3) 0.9586(2) -0.09461(12) 0.0631(6) Uani d . 1 . . C
  H22 0.3738 0.9824 -0.1356 0.076 Uiso calc R 1 . . H
  C5 0.2815(4) 0.5002(2) 0.14315(15) 0.0791(8) Uani d . 1 . . C
  H5A 0.2641 0.4475 0.1784 0.095 Uiso calc R 1 . . H
  H5B 0.3415 0.4628 0.1093 0.095 Uiso calc R 1 . . H
  C27 0.0639(3) 1.10198(19) 0.16994(12) 0.0599(6) Uani d . 1 . . C
  C7 0.5242(4) 0.5789(2) 0.20656(14) 0.0770(8) Uani d . 1 . . C
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
  Cl34 0.1194(6) 0.0595(4) 0.0702(4) -0.0090(4) 0.0330(4) -0.0114(3)
  Cl14 0.0816(5) 0.0773(5) 0.1172(6) -0.0204(4) -0.0026(4) -0.0196(4)
  O15 0.1234(19) 0.0840(15) 0.1296(19) 0.0358(14) 0.0028(15) 0.0475(14)
  O35 0.1103(15) 0.0419(9) 0.0839(12) 0.0167(9) 0.0054(11) -0.0100(8)
  N26 0.0621(11) 0.0306(8) 0.0578(10) 0.0001(7) 0.0034(8) -0.0003(7)
  N6 0.0870(14) 0.0412(10) 0.0650(11) 0.0135(9) 0.0146(10) 0.0150(9)
  C31 0.0563(11) 0.0291(9) 0.0548(11) -0.0039(8) 0.0035(9) 0.0037(8)
  C13 0.0756(15) 0.0349(10) 0.0624(13) -0.0069(10) 0.0141(11) -0.0043(9)
  C10 0.0764(15) 0.0368(10) 0.0521(11) 0.0045(10) 0.0127(11) 0.0077(9)
  C29 0.0916(18) 0.0515(13) 0.0610(13) -0.0030(12) 0.0182(12) 0.0006(11)
  C30 0.0581(12) 0.0341(10) 0.0535(11) -0.0044(9) 0.0017(9) 0.0027(8)
  C33 0.0646(13) 0.0317(10) 0.0597(12) -0.0056(9) 0.0081(10) 0.0020(9)
  C21 0.0663(14) 0.0452(11) 0.0585(12) -0.0029(10) 0.0099(10) -0.0023(10)
  C12 0.0766(15) 0.0292(9) 0.0529(11) -0.0050(9) 0.0196(10) 0.0004(8)
  C32 0.0501(11) 0.0314(9) 0.0546(11) -0.0044(8) 0.0023(9) 0.0041(8)
  C11 0.0710(14) 0.0288(9) 0.0527(11) -0.0008(9) 0.0114(10) 0.0043(8)
  C23 0.0704(14) 0.0368(11) 0.0679(14) 0.0003(10) 0.0099(11) 0.0132(10)
  C9 0.0784(17) 0.0569(14) 0.0657(14) 0.0038(12) -0.0001(12) 0.0064(11)
  C28 0.0959(19) 0.0598(15) 0.0667(15) 0.0040(14) 0.0157(14) -0.0053(12)
  C8 0.0796(18) 0.085(2) 0.0693(16) 0.0173(15) 0.0052(13) 0.0117(14)
  C4 0.0948(18) 0.0296(10) 0.0618(13) 0.0015(11) 0.0240(12) 0.0024(9)
  C24 0.0516(11) 0.0319(9) 0.0601(12) -0.0011(8) 0.0025(9) 0.0064(8)
  C1 0.0800(16) 0.0491(13) 0.0693(14) -0.0145(12) 0.0174(12) -0.0132(11)
  C3 0.124(2) 0.0275(10) 0.0779(16) -0.0110(13) 0.0325(17) -0.0016(10)
  C25 0.0842(16) 0.0320(10) 0.0733(14) -0.0026(10) 0.0177(12) 0.0042(10)
  C2 0.104(2) 0.0452(13) 0.0822(18) -0.0265(14) 0.0233(16) -0.0123(12)
  C22 0.0798(16) 0.0524(13) 0.0581(13) -0.0046(11) 0.0138(11) 0.0115(11)
  C5 0.114(2) 0.0333(11) 0.0918(19) 0.0117(13) 0.0237(17) 0.0100(12)
  C27 0.0692(14) 0.0468(12) 0.0634(13) 0.0066(11) -0.0011(11) -0.0075(10)
  C7 0.0917(19) 0.0699(17) 0.0709(16) 0.0243(15) 0.0178(14) 0.0227(13)
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
  Cl34 C21 . 1.741(2) ?
  Cl14 C1 . 1.746(3) ?
  O15 C7 . 1.220(3) ?
  O35 C27 . 1.209(3) ?
  N26 C27 . 1.370(3) ?
  N26 C30 . 1.391(2) ?
  N26 C25 . 1.445(3) ?
  N6 C7 . 1.358(4) ?
  N6 C10 . 1.402(3) ?
  N6 C5 . 1.461(4) ?
  C31 C30 . 1.342(3) ?
  C31 C32 . 1.470(3) ?
  C31 C11 . 1.493(3) ?
  C13 C1 . 1.376(3) ?
  C13 C12 . 1.383(3) ?
  C13 H13 . 0.9300 ?
  C10 C11 . 1.330(3) ?
  C10 C9 . 1.496(3) ?
  C29 C30 . 1.503(3) ?
  C29 C28 . 1.531(4) ?
  C29 H29A . 0.9700 ?
  C29 H29B . 0.9700 ?
  C33 C21 . 1.373(3) ?
  C33 C32 . 1.393(3) ?
  C33 H33 . 0.9300 ?
  C21 C22 . 1.378(3) ?
  C12 C4 . 1.402(3) ?
  C12 C11 . 1.480(3) ?
  C32 C24 . 1.406(3) ?
  C23 C24 . 1.376(3) ?
  C23 C22 . 1.384(3) ?
  C23 H23 . 0.9300 ?
  C9 C8 . 1.519(4) ?
  C9 H9A . 0.9700 ?
  C9 H9B . 0.9700 ?
  C28 C27 . 1.502(4) ?
  C28 H28A . 0.9700 ?
  C28 H28B . 0.9700 ?
  C8 C7 . 1.501(4) ?
  C8 H8A . 0.9700 ?
  C8 H8B . 0.9700 ?
  C4 C3 . 1.392(4) ?
  C4 C5 . 1.497(4) ?
  C24 C25 . 1.502(3) ?
  C1 C2 . 1.368(4) ?
  C3 C2 . 1.380(4) ?
  C3 H3 . 0.9300 ?
  C25 H25A . 0.9700 ?
  C25 H25B . 0.9700 ?
  C2 H2 . 0.9300 ?
  C22 H22 . 0.9300 ?
  C5 H5A . 0.9700 ?
  C5 H5B . 0.9700 ?