#------------------------------------------------------------------------------
#$Date: 2011-03-31 12:48:06 +0100 (Thu, 31 Mar 2011) $
#$Revision: 17004 $
#$URL: svn://www.crystallography.net/cod/cif/2/2011657.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_2011657
loop_
_publ_author_name
'Lynch, Daniel E.'
'McClenaghan, Ian'
_publ_section_title
;
2-Chloro-3-(pyrrolidin-1-yl)-1,4-naphthoquinone
;
_journal_name_full               'Acta Crystallographica, Section C'
_journal_page_first              e588
_journal_page_last               e588
_journal_volume                  56
_journal_year                    2000
_chemical_formula_sum            'C14 H12 Cl N O2'
_chemical_formula_weight         261.70
_chemical_melting_point          372.0(10)
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 115.829(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2926(6)
_cell_length_b                   10.4429(4)
_cell_length_c                   11.2028(4)
_cell_measurement_temperature    150(2)
_cell_volume                     1189.14(9)
_diffrn_ambient_temperature      150(2)
_exptl_crystal_density_diffrn    1.462
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '371 - 373 K' was changed to
'372.0(10)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               2011657
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'
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 .72406(19) .57168(17) .20910(17) .0340(4) Uani d . 1 . . C
O1 .80999(13) .49279(13) .27202(13) .0455(4) Uani d . 1 . . O
C2 .58666(18) .54950(15) .17490(17) .0311(4) Uani d . 1 . . C
Cl2 .55843(5) .39676(4) .21805(5) .04187(19) Uani d . 1 . . Cl
C3 .48609(18) .63550(15) .10887(16) .0295(4) Uani d . 1 . . C
N31 .36071(15) .62397(13) .09139(14) .0333(4) Uani d . 1 . . N
C32 .24495(18) .69738(19) -.00469(19) .0400(5) Uani d . 1 . . C
H321 .2378 .6911 -.0958 .050 Uiso calc R 1 . . H
H322 .2505 .7887 .0208 .050 Uiso calc R 1 . . H
C33 .1295(2) .6316(2) .0057(2) .0495(5) Uani d . 1 . . C
H331 .0534 .6902 -.0198 .062 Uiso calc R 1 . . H
H332 .1018 .5540 -.0505 .062 Uiso calc R 1 . . H
C34 .1864(2) .5978(2) .1514(2) .0500(6) Uani d . 1 . . C
H341 .1319 .5330 .1688 .062 Uiso calc R 1 . . H
H342 .1948 .6745 .2065 .062 Uiso calc R 1 . . H
C35 .3197(2) .54435(19) .17666(19) .0405(5) Uani d . 1 . . C
H351 .3826 .5529 .2713 .051 Uiso calc R 1 . . H
H352 .3132 .4530 .1511 .051 Uiso calc R 1 . . H
C4 .52273(18) .75446(16) .05398(16) .0312(4) Uani d . 1 . . C
O4 .43884(13) .83136(11) -.01240(13) .0410(4) Uani d . 1 . . O
C5 .6960(2) .88599(16) .03419(19) .0389(5) Uani d . 1 . . C
H5 .6298 .9448 -.0189 .049 Uiso calc R 1 . . H
C6 .8252(2) .90886(18) .0622(2) .0461(5) Uani d . 1 . . C
H6 .8479 .9830 .0276 .058 Uiso calc R 1 . . H
C7 .9229(2) .82417(19) .1408(2) .0476(5) Uani d . 1 . . C
H7 1.0123 .8411 .1613 .060 Uiso calc R 1 . . H
C8 .88945(19) .71527(19) .1892(2) .0434(5) Uani d . 1 . . C
H8 .9561 .6567 .2421 .054 Uiso calc R 1 . . H
C9 .75917(18) .69085(16) .16107(17) .0339(4) Uani d . 1 . . C
C10 .66167(18) .77668(16) .08350(17) .0312(4) 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 .0365(12) .0342(9) .0304(10) .0066(8) .0137(9) -.0013(8)
O1 .0406(8) .0440(7) .0480(8) .0154(6) .0156(7) .0106(6)
C2 .0383(11) .0274(9) .0292(9) .0021(8) .0162(8) .0017(7)
Cl2 .0555(4) .0306(3) .0446(3) .0030(2) .0265(3) .00587(19)
C3 .0338(11) .0302(9) .0260(9) .0006(7) .0144(8) -.0036(7)
N31 .0307(9) .0378(8) .0313(8) .0018(6) .0133(7) -.0002(7)
C32 .0324(11) .0472(11) .0353(11) .0054(9) .0100(9) -.0002(8)
C33 .0314(12) .0703(14) .0444(12) -.0009(10) .0143(10) -.0043(10)
C34 .0349(12) .0737(15) .0435(12) -.0062(10) .0190(10) -.0048(11)
C35 .0379(12) .0514(12) .0348(10) -.0034(9) .0182(9) .0010(9)
C4 .0381(11) .0284(9) .0288(9) .0035(8) .0161(8) -.0028(7)
O4 .0414(8) .0355(7) .0453(8) .0106(6) .0183(7) .0082(6)
C5 .0467(13) .0322(10) .0401(11) -.0013(8) .0210(10) -.0011(8)
C6 .0540(15) .0407(11) .0502(13) -.0127(10) .0288(11) -.0071(9)
C7 .0376(13) .0502(12) .0579(14) -.0092(10) .0234(11) -.0097(10)
C8 .0319(12) .0469(11) .0463(12) .0019(9) .0124(10) -.0047(9)
C9 .0355(12) .0344(9) .0323(10) .0013(8) .0151(9) -.0041(8)
C10 .0358(11) .0301(9) .0278(9) .0003(8) .0140(8) -.0039(7)
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 . 1.233(2) ?
C1 C2 . 1.446(3) ?
C1 C9 . 1.477(3) ?
C2 C3 . 1.383(2) ?
C2 Cl2 . 1.7361(17) ?
C3 N31 . 1.348(2) ?
C3 C4 . 1.521(2) ?
N31 C35 . 1.484(2) ?
N31 C32 . 1.493(2) ?
C32 C33 . 1.523(3) ?
C32 H321 . .9900 ?
C32 H322 . .9900 ?
C33 C34 . 1.512(3) ?
C33 H331 . .9900 ?
C33 H332 . .9900 ?
C34 C35 . 1.513(3) ?
C34 H341 . .9900 ?
C34 H342 . .9900 ?
C35 H351 . .9900 ?
C35 H352 . .9900 ?
C4 O4 . 1.217(2) ?
C4 C10 . 1.474(3) ?
C5 C6 . 1.373(3) ?
C5 C10 . 1.395(3) ?
C5 H5 . .9500 ?
C6 C7 . 1.389(3) ?
C6 H6 . .9500 ?
C7 C8 . 1.381(3) ?
C7 H7 . .9500 ?
C8 C9 . 1.387(3) ?
C8 H8 . .9500 ?
C9 C10 . 1.392(2) ?