#------------------------------------------------------------------------------
#$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: svn://www.crystallography.net/cod/cif/2/2013075.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_2013075
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o704
_journal_page_last  o707
_publ_section_title
;
2-(Pyrrolidin-1-yl)-1,4-naphthoquinone and
2-(phenylsulfanyl)-3-(pyrrolidin-1-yl)-1,4-naphthoquinone
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_[local]_cod_cif_authors_sg_Hall -P2ybc
loop_
_publ_author_name
  'Lynch, Daniel E.'
  'Ian McClenaghan'
_chemical_formula_moiety  'C20 H17 N O2 S'
_chemical_formula_sum  'C20 H17 N O2 S'
_chemical_formula_iupac  'C20 H17 N O2 S'
_chemical_formula_weight  335.42
_symmetry_cell_setting  Monoclinic
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  13.205(3)
_cell_length_b  11.387(2)
_cell_length_c  11.220(2)
_cell_angle_alpha  90
_cell_angle_beta  93.12(3)
_cell_angle_gamma  90
_cell_volume  1684.6(6)
_cell_formula_units_Z  4
_cell_measurement_temperature  150(2)
_exptl_crystal_density_diffrn  1.322
_diffrn_ambient_temperature  150(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
  C1 0.40096(16) 0.74543(19) -0.03400(17) 0.0485(5) Uani d . 1 . . C
  O1 0.47061(12) 0.81306(15) -0.05171(15) 0.0744(5) Uani d . 1 . . O
  C2 0.31222(14) 0.78222(18) 0.03657(15) 0.0409(5) Uani d . 1 . . C
  N21 0.27978(12) 0.89343(15) 0.02664(13) 0.0467(4) Uani d . 1 . . N
  C22 0.17644(17) 0.93098(19) 0.05505(18) 0.0570(6) Uani d . 1 . . C
  H221 0.1748 0.9568 0.1392 0.071 Uiso calc R 1 . . H
  H222 0.1270 0.8665 0.0409 0.071 Uiso calc R 1 . . H
  C23 0.15373(19) 1.0331(2) -0.0305(2) 0.0693(7) Uani d . 1 . . C
  H231 0.1290 1.0047 -0.1102 0.087 Uiso calc R 1 . . H
  H232 0.1028 1.0870 0.0010 0.087 Uiso calc R 1 . . H
  C24 0.2560(2) 1.0924(2) -0.0356(2) 0.0769(8) Uani d . 1 . . C
  H241 0.2711 1.1412 0.0362 0.096 Uiso calc R 1 . . H
  H242 0.2588 1.1423 -0.1076 0.096 Uiso calc R 1 . . H
  C25 0.32974(18) 0.98972(18) -0.04050(19) 0.0585(6) Uani d . 1 . . C
  H251 0.3393 0.9660 -0.1240 0.073 Uiso calc R 1 . . H
  H252 0.3965 1.0103 -0.0017 0.073 Uiso calc R 1 . . H
  C3 0.27236(14) 0.69487(18) 0.11022(15) 0.0435(5) Uani d . 1 . . C
  S3 0.22008(4) 0.73593(5) 0.24541(4) 0.0527(2) Uani d . 1 . . S
  C31 0.08772(15) 0.71279(18) 0.23074(16) 0.0472(5) Uani d . 1 . . C
  C32 0.0299(2) 0.7770(2) 0.3067(2) 0.0748(7) Uani d . 1 . . C
  H32 0.0620 0.8313 0.3608 0.093 Uiso calc R 1 . . H
  C33 -0.0739(2) 0.7628(3) 0.3043(3) 0.0905(9) Uani d . 1 . . C
  H33 -0.1126 0.8075 0.3570 0.113 Uiso calc R 1 . . H
  C34 -0.12134(19) 0.6862(3) 0.2280(2) 0.0761(7) Uani d . 1 . . C
  H34 -0.1928 0.6763 0.2276 0.095 Uiso calc R 1 . . H
  C35 -0.0653(2) 0.6227(3) 0.1513(2) 0.0817(8) Uani d . 1 . . C
  H35 -0.0984 0.5695 0.0969 0.102 Uiso calc R 1 . . H
  C36 0.03861(18) 0.6353(2) 0.1523(2) 0.0713(7) Uani d . 1 . . C
  H36 0.0766 0.5906 0.0989 0.089 Uiso calc R 1 . . H
  C4 0.28995(15) 0.57049(19) 0.08875(17) 0.0482(5) Uani d . 1 . . C
  O4 0.25770(12) 0.49153(13) 0.15308(13) 0.0696(5) Uani d . 1 . . O
  C5 0.34672(17) 0.4205(2) -0.0580(2) 0.0628(6) Uani d . 1 . . C
  H5 0.3114 0.3617 -0.0168 0.078 Uiso calc R 1 . . H
  C6 0.39965(18) 0.3910(2) -0.1568(2) 0.0748(7) Uani d . 1 . . C
  H6 0.3990 0.3122 -0.1845 0.094 Uiso calc R 1 . . H
  C7 0.45313(19) 0.4748(3) -0.2154(2) 0.0757(8) Uani d . 1 . . C
  H7 0.4884 0.4537 -0.2838 0.095 Uiso calc R 1 . . H
  C8 0.45590(16) 0.5905(2) -0.17482(19) 0.0651(7) Uani d . 1 . . C
  H8 0.4951 0.6475 -0.2134 0.081 Uiso calc R 1 . . H
  C9 0.40071(14) 0.62191(19) -0.07721(17) 0.0472(5) Uani d . 1 . . C
  C10 0.34553(14) 0.53670(18) -0.01917(16) 0.0462(5) 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
  C1 0.0413(12) 0.0558(15) 0.0483(12) -0.0027(10) 0.0011(9) 0.0128(10)
  O1 0.0555(10) 0.0679(12) 0.1015(12) -0.0126(9) 0.0204(9) 0.0143(10)
  C2 0.0432(12) 0.0439(13) 0.0352(10) -0.0073(9) -0.0023(8) -0.0002(8)
  N21 0.0546(11) 0.0412(11) 0.0443(9) -0.0049(8) 0.0039(7) 0.0006(7)
  C22 0.0644(15) 0.0480(15) 0.0590(13) 0.0039(11) 0.0067(10) -0.0024(10)
  C23 0.0832(19) 0.0497(16) 0.0745(15) 0.0118(13) 0.0008(12) 0.0029(12)
  C24 0.109(2) 0.0426(16) 0.0787(17) -0.0033(14) 0.0045(14) 0.0052(12)
  C25 0.0741(16) 0.0428(14) 0.0588(13) -0.0144(12) 0.0050(10) 0.0072(10)
  C3 0.0452(12) 0.0465(14) 0.0385(10) -0.0030(9) 0.0013(8) 0.0027(9)
  S3 0.0553(4) 0.0670(4) 0.0358(3) -0.0066(3) 0.0016(2) -0.0014(2)
  C31 0.0538(13) 0.0488(13) 0.0394(10) -0.0003(10) 0.0059(9) 0.0075(9)
  C32 0.0685(18) 0.083(2) 0.0739(17) -0.0019(14) 0.0136(13) -0.0202(14)
  C33 0.071(2) 0.109(3) 0.094(2) 0.0108(17) 0.0256(16) -0.0120(17)
  C34 0.0525(16) 0.090(2) 0.0860(18) -0.0001(15) 0.0057(13) 0.0237(16)
  C35 0.0639(18) 0.090(2) 0.0899(19) -0.0077(15) -0.0096(14) -0.0066(15)
  C36 0.0583(16) 0.082(2) 0.0732(15) -0.0025(13) 0.0029(12) -0.0227(13)
  C4 0.0452(12) 0.0473(15) 0.0520(12) -0.0054(10) 0.0009(9) 0.0086(10)
  O4 0.0844(13) 0.0510(11) 0.0753(10) -0.0041(8) 0.0220(8) 0.0151(8)
  C5 0.0550(15) 0.0571(17) 0.0757(15) 0.0020(11) -0.0004(11) -0.0072(12)
  C6 0.0621(17) 0.076(2) 0.0859(18) 0.0122(14) -0.0018(13) -0.0267(15)
  C7 0.0593(17) 0.102(2) 0.0659(15) 0.0185(15) 0.0056(12) -0.0232(15)
  C8 0.0517(14) 0.084(2) 0.0610(14) 0.0104(12) 0.0104(10) 0.0044(13)
  C9 0.0381(12) 0.0551(15) 0.0481(11) 0.0047(10) -0.0005(8) 0.0035(10)
  C10 0.0407(12) 0.0482(14) 0.0490(11) 0.0023(10) -0.0036(8) -0.0014(10)
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
  C1 O1 . 1.224(2) ?
  C1 C9 . 1.488(3) ?
  C1 C2 . 1.509(3) ?
  C2 N21 . 1.340(2) ?
  C2 C3 . 1.413(3) ?
  N21 C22 . 1.481(3) ?
  N21 C25 . 1.503(2) ?
  C22 C23 . 1.527(3) ?
  C22 H221 . 0.99 ?
  C22 H222 . 0.99 ?
  C23 C24 . 1.514(3) ?
  C23 H231 . 0.99 ?
  C23 H232 . 0.99 ?
  C24 C25 . 1.524(3) ?
  C24 H241 . 0.99 ?
  C24 H242 . 0.99 ?
  C25 H251 . 0.99 ?
  C25 H252 . 0.99 ?
  C3 C4 . 1.457(3) ?
  C3 S3 . 1.7636(19) ?
  S3 C31 . 1.766(2) ?
  C31 C36 . 1.383(3) ?
  C31 C32 . 1.384(3) ?
  C32 C33 . 1.379(3) ?
  C32 H32 . 0.95 ?
  C33 C34 . 1.352(4) ?
  C33 H33 . 0.95 ?
  C34 C35 . 1.371(3) ?
  C34 H34 . 0.95 ?
  C35 C36 . 1.379(3) ?
  C35 H35 . 0.95 ?
  C36 H36 . 0.95 ?
  C4 O4 . 1.243(2) ?
  C4 C10 . 1.500(3) ?
  C5 C6 . 1.384(3) ?
  C5 C10 . 1.394(3) ?
  C5 H5 . 0.95 ?
  C6 C7 . 1.375(4) ?
  C6 H6 . 0.95 ?
  C7 C8 . 1.393(4) ?
  C7 H7 . 0.95 ?
  C8 C9 . 1.395(3) ?
  C8 H8 . 0.95 ?
  C9 C10 . 1.396(3) ?
_cod_database_code 2013075