data_2011560
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  e537
_journal_page_last  e537
_publ_section_title
;
2-Chloro-3-morpholino-1,4-naphthoquinone
;
loop_
_publ_author_name
  'Lynch, Daniel E.'
  'McClenaghan, Ian'
_chemical_formula_sum  'C14 H12 Cl N O3'
_chemical_formula_weight  277.70
_chemical_melting_point  '428 - 430 K'
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P -1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  5.03860(10)
_cell_length_b  10.3948(2)
_cell_length_c  12.7421(3)
_cell_angle_alpha  67.2038(12)
_cell_angle_beta  84.4066(10)
_cell_angle_gamma  81.2678(12)
_cell_volume  607.56(2)
_cell_formula_units_Z  2
_cell_measurement_temperature  150(2)
_exptl_crystal_density_diffrn  1.518
_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  .5044(3)  .20176(14)  .10486(11)  .0230(3) Uani d . 1 . . C
  O1  .4184(2)  .28268(11)  .01277(9)  .0345(3) Uani d . 1 . . O
  C2  .4346(3)  .05762(14)  .15913(11)  .0209(3) Uani d . 1 . . C
  Cl2  .20776(6)  .01615(3)  .08691(3)  .02830(17) Uani d . 1 . . Cl
  C3  .5264(2)  -.03813(13)  .26084(11)  .0203(3) Uani d . 1 . . C
  N31  .4885(2)  -.17681(12)  .30333(10)  .0247(3) Uani d . 1 . . N
  C32  .4332(3)  -.26062(15)  .42384(12)  .0280(3) Uani d . 1 . . C
  H111  .3748  -.1981  .4661  .035 Uiso calc R 1 . . H
  H112  .5974  -.3226  .4581  .035 Uiso calc R 1 . . H
  C33  .2117(3)  -.34858(15)  .43056(13)  .0329(3) Uani d . 1 . . C
  H121  .1748  -.4083  .5112  .041 Uiso calc R 1 . . H
  H122  .0451  -.2853  .4012  .041 Uiso calc R 1 . . H
  O34  .2832(2)  -.43609(10)  .36633(9)  .0344(3) Uani d . 1 . . O
  C35  .3313(3)  -.35325(15)  .24931(13)  .0303(3) Uani d . 1 . . C
  H131  .1645  -.2919  .2177  .038 Uiso calc R 1 . . H
  H132  .3831  -.4156  .2065  .038 Uiso calc R 1 . . H
  C36  .5524(3)  -.26367(14)  .23482(12)  .0244(3) Uani d . 1 . . C
  H141  .7240  -.3250  .2586  .030 Uiso calc R 1 . . H
  H142  .5746  -.2023  .1535  .030 Uiso calc R 1 . . H
  C4  .6912(3)  .01070(14)  .32853(12)  .0230(3) Uani d . 1 . . C
  O4  .7648(3)  -.06883(11)  .42194(10)  .0419(3) Uani d . 1 . . O
  C5  .9383(3)  .19717(14)  .33317(12)  .0242(3) Uani d . 1 . . C
  H5  .9982  .1350  .4061  .030 Uiso calc R 1 . . H
  C6 1.0187(3)  .33047(15)  .28378(13)  .0293(3) Uani d . 1 . . C
  H6 1.1341  .3596  .3227  .037 Uiso calc R 1 . . H
  C7  .9300(3)  .42136(14)  .17709(13)  .0304(3) Uani d . 1 . . C
  H7  .9838  .5129  .1438  .038 Uiso calc R 1 . . H
  C8  .7641(3)  .37966(14)  .11893(12)  .0274(3) Uani d . 1 . . C
  H8  .7053  .4422  .0459  .034 Uiso calc R 1 . . H
  C9  .6838(3)  .24580(13)  .16766(11)  .0203(3) Uani d . 1 . . C
  C10  .7691(3)  .15463(13)  .27548(11)  .0206(3) 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  .0255(7)  .0223(7)  .0224(7)  .0005(5)  -.0045(5)  -.0100(5)
  O1  .0511(7)  .0251(5)  .0262(6)  -.0009(5)  -.0165(5)  -.0064(4)
  C2  .0199(6)  .0245(6)  .0225(7)  -.0037(5)  -.0035(5)  -.0124(5)
  Cl2  .0250(2)  .0357(3)  .0301(3)  -.00578(16)  -.00844(16)  -.01645(18)
  C3  .0202(6)  .0223(6)  .0212(7)  -.0059(5)  -.0001(5)  -.0103(5)
  N31  .0335(7)  .0221(6)  .0221(6)  -.0111(5)  .0015(5)  -.0101(5)
  C32  .0349(8)  .0251(7)  .0240(7)  -.0115(6)  .0004(6)  -.0070(6)
  C33  .0363(8)  .0305(8)  .0325(8)  -.0139(6)  .0072(6)  -.0109(6)
  O34  .0421(6)  .0267(5)  .0379(6)  -.0167(5)  .0042(5)  -.0129(5)
  C35  .0319(7)  .0291(7)  .0357(8)  -.0140(6)  .0003(6)  -.0152(6)
  C36  .0248(7)  .0241(6)  .0290(7)  -.0080(5)  .0010(5)  -.0138(6)
  C4  .0274(7)  .0198(6)  .0229(7)  -.0038(5)  -.0065(5)  -.0078(5)
  O4  .0642(8)  .0265(6)  .0332(6)  -.0144(5)  -.0259(6)  -.0006(5)
  C5  .0280(7)  .0243(6)  .0239(7)  -.0047(5)  -.0044(5)  -.0119(6)
  C6  .0313(7)  .0303(7)  .0335(8)  -.0102(6)  -.0014(6)  -.0176(6)
  C7  .0372(8)  .0225(7)  .0355(8)  -.0117(6)  .0024(6)  -.0135(6)
  C8  .0327(7)  .0228(7)  .0253(7)  -.0032(6)  -.0019(6)  -.0075(6)
  C9  .0230(6)  .0185(6)  .0213(6)  -.0013(5)  -.0021(5)  -.0097(5)
  C10  .0229(7)  .0187(6)  .0219(7)  -.0016(5)  -.0027(5)  -.0094(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
  C1 O1 . 1.2229(17) ?
  C1 C2 . 1.4685(19) ?
  C1 C9 . 1.4892(17) ?
  C2 C3 . 1.3645(19) ?
  C2 Cl2 . 1.7322(12) ?
  C3 N31 . 1.3661(16) ?
  C3 C4 . 1.5160(17) ?
  N31 C32 . 1.4657(18) ?
  N31 C36 . 1.4658(15) ?
  C32 C33 . 1.5230(18) ?
  C32 H111 .  .9900 ?
  C32 H112 .  .9900 ?
  C33 O34 . 1.4307(16) ?
  C33 H121 .  .9900 ?
  C33 H122 .  .9900 ?
  O34 C35 . 1.4218(18) ?
  C35 C36 . 1.5110(17) ?
  C35 H131 .  .9900 ?
  C35 H132 .  .9900 ?
  C36 H141 .  .9900 ?
  C36 H142 .  .9900 ?
  C4 O4 . 1.2116(18) ?
  C4 C10 . 1.4806(18) ?
  C5 C6 . 1.3875(19) ?
  C5 C10 . 1.3968(17) ?
  C5 H5 .  .9500 ?
  C6 C7 . 1.391(2) ?
  C6 H6 .  .9500 ?
  C7 C8 . 1.384(2) ?
  C7 H7 .  .9500 ?
  C8 C9 . 1.3922(19) ?
  C8 H8 .  .9500 ?
  C9 C10 . 1.3975(18) ?