#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2200332.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_2200332
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2001
_journal_volume  57
_journal_page_first  o389
_journal_page_last  o391
_publ_section_title
;
1-(2-Chlorophenyl)-N-methyl-N-(1-methylpropyl)isoquinoline-3-carboxamide
;
loop_
_publ_author_name
  'Kubicki, Maciej'
  'Codding, Penelope W.'
_chemical_name_common  'PK11195'
_chemical_formula_moiety  'C21 H21 Cl N2 O'
_chemical_formula_sum  'C21 H21 Cl N2 O'
_chemical_formula_iupac  'C21 H21 Cl N2 O'
_chemical_formula_weight  352.85
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
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  10.365(2)
_cell_length_b  15.529(4)
_cell_length_c  11.767(3)
_cell_angle_alpha  90.00
_cell_angle_beta  93.33(2)
_cell_angle_gamma  90.00
_cell_volume  1890.8(8)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.240
_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
  C1  .9486(3)  .23215(18)  .4205(2)  .0469(7) Uani d . 1 . . C
  C1'  .8930(3)  .1463(2)  .4479(3)  .0564(8) Uani d D 1 A . C
  C2'  .8570(3)  .0891(2)  .3638(3)  .0612(9) Uani d . 1 . . C
  H2B  .8634  .1049  .2882  .073 Uiso calc PR  .064(2) A 1 H
  Cl2A  .86755(12)  .11831(7)  .22397(8)  .0801(4) Uani d P  .936(2) A 2 Cl
  C3'  .8107(4)  .0073(2)  .3891(4)  .0853(13) Uani d . 1 A . C
  H3'  .7860  -.0311  .3312  .102 Uiso calc R 1 . . H
  C4'  .8025(4)  -.0151(3)  .5000(5)  .0910(13) Uani d . 1 . . C
  H4'  .7745  -.0701  .5176  .109 Uiso calc R 1 A . H
  C5'  .8338(5)  .0403(3)  .5851(4)  .1032(15) Uani d D 1 A . C
  H5'  .8251  .0229  .6599  .124 Uiso calc R 1 . . H
  C6'  .8797(3)  .1243(3)  .5641(4)  .0957(15) Uani d D 1 . . C
  H6A  .9000  .1630  .6228  .115 Uiso calc PR  .936(2) A 1 H
  Cl6B  .9168(13)  .1953(7)  .6710(9)  .122 Uiso d PD  .064(2) A 2 Cl
  N2 1.0708(2)  .23158(15)  .3962(2)  .0501(6) Uani d . 1 . . N
  C3 1.1277(3)  .30875(19)  .3754(2)  .0453(7) Uani d . 1 . . C
  C4 1.0654(3)  .38537(19)  .3793(2)  .0472(7) Uani d . 1 . . C
  H4 1.1094  .4363  .3662  .057 Uiso calc R 1 . . H
  C4a  .9335(3)  .38763(18)  .4033(2)  .0446(7) Uani d . 1 . . C
  C5  .8620(3)  .46484(19)  .4094(3)  .0540(8) Uani d . 1 . . C
  H5  .9021  .5173  .3973  .065 Uiso calc R 1 . . H
  C6  .7356(3)  .4631(2)  .4329(3)  .0605(8) Uani d . 1 . . C
  H6  .6895  .5142  .4370  .073 Uiso calc R 1 . . H
  C7  .6741(3)  .3842(2)  .4510(3)  .0620(9) Uani d . 1 . . C
  H7  .5869  .3834  .4654  .074 Uiso calc R 1 . . H
  C8  .7401(3)  .3093(2)  .4478(3)  .0540(8) Uani d . 1 . . C
  H8  .6980  .2576  .4608  .065 Uiso calc R 1 . . H
  C8a  .8725(3)  .30848(18)  .4247(2)  .0441(7) Uani d . 1 . . C
  C31 1.2704(3)  .3049(2)  .3562(3)  .0496(7) Uani d . 1 B . C
  O31 1.3445(2)  .34467(16)  .4223(2)  .0708(7) Uani d . 1 . . O
  N31 1.3089(2)  .2586(2)  .2697(3)  .0685(9) Uani d D 1 . . N
  C32A 1.2164(11)  .2327(9)  .1757(11)  .076(4) Uani d PD  .624(9) B 1 C
  H32A 1.2606  .1997  .1210  .092 Uiso calc PR  .624(9) B 1 H
  H32B 1.1795  .2832  .1397  .092 Uiso calc PR  .624(9) B 1 H
  H32C 1.1490  .1985  .2054  .092 Uiso calc PR  .624(9) B 1 H
  C33A 1.4472(7)  .2607(6)  .2448(8)  .063(2) Uani d PD  .624(9) B 1 C
  H33A 1.4951  .2772  .3156  .076 Uiso calc PR  .624(9) B 1 H
  C34A 1.4848(16)  .3240(7)  .1547(15)  .102(4) Uani d PD  .624(9) B 1 C
  H34A 1.4576  .3808  .1748  .123 Uiso calc PR  .624(9) B 1 H
  H34B 1.4438  .3081  .0825  .123 Uiso calc PR  .624(9) B 1 H
  H34C 1.5769  .3233  .1497  .123 Uiso calc PR  .624(9) B 1 H
  C35A 1.4883(8)  .1691(5)  .2180(7)  .081(2) Uani d PD  .624(9) B 1 C
  H35A 1.5805  .1687  .2080  .097 Uiso calc PR  .624(9) B 1 H
  H35B 1.4450  .1516  .1463  .097 Uiso calc PR  .624(9) B 1 H
  C36A 1.459(2)  .1030(7)  .3091(16)  .124(5) Uani d PD  .624(9) B 1 C
  H36A 1.4868  .0470  .2862  .149 Uiso calc PR  .624(9) B 1 H
  H36B 1.3672  .1018  .3185  .149 Uiso calc PR  .624(9) B 1 H
  H36C 1.5032  .1185  .3799  .149 Uiso calc PR  .624(9) B 1 H
  C32B 1.2261(17)  .1992(14)  .199(2)  .085(8) Uani d PD  .376(9) B 2 C
  H32D 1.2764  .1734  .1416  .102 Uiso calc PR  .376(9) B 2 H
  H32E 1.1556  .2309  .1624  .102 Uiso calc PR  .376(9) B 2 H
  H32F 1.1929  .1550  .2459  .102 Uiso calc PR  .376(9) B 2 H
  C33B 1.4506(11)  .2290(9)  .2770(13)  .064(4) Uani d PDU  .376(9) B 2 C
  H33B 1.4941  .2577  .3429  .077 Uiso calc PR  .376(9) B 2 H
  C34B 1.472(2)  .1334(11)  .291(3)  .124(10) Uani d PDU  .376(9) B 2 C
  H34D 1.4351  .1145  .3601  .149 Uiso calc PR  .376(9) B 2 H
  H34E 1.5628  .1214  .2955  .149 Uiso calc PR  .376(9) B 2 H
  H34F 1.4309  .1036  .2275  .149 Uiso calc PR  .376(9) B 2 H
  C35B 1.5071(12)  .2652(10)  .1705(12)  .097(5) Uani d PDU  .376(9) B 2 C
  H35C 1.5985  .2514  .1728  .117 Uiso calc PR  .376(9) B 2 H
  H35D 1.4663  .2364  .1046  .117 Uiso calc PR  .376(9) B 2 H
  C36B 1.492(4)  .3609(13)  .154(3)  .155(13) Uani d PDU  .376(9) B 2 C
  H36D 1.5289  .3778  .0850  .186 Uiso calc PR  .376(9) B 2 H
  H36E 1.5350  .3904  .2174  .186 Uiso calc PR  .376(9) B 2 H
  H36F 1.4016  .3754  .1506  .186 Uiso calc PR  .376(9) B 2 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
  C1  .0415(16)  .0483(16)  .0516(18)  -.0031(13)  .0072(13)  -.0017(13)
  C1'  .0427(17)  .0470(17)  .080(2)  -.0012(14)  .0105(15)  .0035(16)
  C2'  .057(2)  .0512(18)  .077(2)  -.0019(16)  .0192(17)  .0016(16)
  Cl2A  .1093(9)  .0711(6)  .0606(6)  -.0157(6)  .0105(5)  -.0101(5)
  C3'  .096(3)  .050(2)  .113(3)  -.005(2)  .031(3)  -.011(2)
  C4'  .096(3)  .070(3)  .109(4)  -.013(2)  .025(3)  .020(3)
  C5'  .113(4)  .099(3)  .100(4)  -.021(3)  .019(3)  .035(3)
  C6'  .073(3)  .101(3)  .116(3)  -.005(2)  .031(2)  .062(3)
  N2  .0417(14)  .0480(14)  .0615(16)  -.0001(11)  .0105(11)  .0022(11)
  C3  .0371(15)  .0526(17)  .0466(16)  -.0034(13)  .0065(12)  -.0034(13)
  C4  .0403(16)  .0483(16)  .0537(17)  -.0071(13)  .0088(13)  -.0043(13)
  C4a  .0406(15)  .0469(15)  .0464(16)  -.0017(13)  .0046(12)  -.0035(12)
  C5  .0530(19)  .0434(16)  .066(2)  .0018(14)  .0049(15)  -.0053(14)
  C6  .0509(19)  .059(2)  .071(2)  .0109(16)  .0046(16)  -.0082(16)
  C7  .0392(16)  .077(2)  .070(2)  .0054(17)  .0081(14)  -.0095(18)
  C8  .0418(17)  .0591(19)  .062(2)  -.0070(15)  .0073(14)  -.0054(15)
  C8a  .0383(15)  .0485(16)  .0455(16)  -.0003(13)  .0031(12)  -.0017(12)
  C31  .0369(16)  .0550(18)  .0573(19)  -.0054(14)  .0074(13)  -.0029(14)
  O31  .0451(13)  .0879(17)  .0802(16)  -.0133(12)  .0093(11)  -.0301(13)
  N31  .0360(14)  .101(2)  .0692(19)  -.0028(14)  .0094(13)  -.0330(16)
  C32A  .046(4)  .120(9)  .062(6)  -.005(5)  -.006(3)  -.036(7)
  C33A  .038(4)  .087(6)  .065(5)  -.001(4)  .012(3)  -.011(4)
  C34A  .083(7)  .095(8)  .134(10)  -.006(7)  .056(7)  .027(8)
  C35A  .054(4)  .094(6)  .095(6)  .013(4)  .012(4)  -.020(4)
  C36A  .146(11)  .083(8)  .143(11)  .031(8)  .002(9)  .003(8)
  C32B  .042(7)  .142(19)  .072(10)  .007(9)  .020(7)  -.023(11)
  C33B  .038(6)  .073(8)  .082(10)  .000(5)  .011(6)  -.018(6)
  C34B  .070(11)  .074(11)  .23(3)  .015(10)  -.009(16)  -.018(12)
  C35B  .054(7)  .157(15)  .083(9)  -.025(9)  .018(6)  -.027(9)
  C36B  .14(2)  .19(2)  .134(18)  .02(2)  .023(15)  .087(19)
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 N2 . 1.315(4) ?
  C1 C8a . 1.426(4) ?
  C1 C1' . 1.495(4) ?
  C1' C2' . 1.366(5) ?
  C1' C6' . 1.423(5) ?
  C2' C3' . 1.395(5) ?
  C2' Cl2A . 1.717(4) ?
  C3' C4' . 1.358(6) ?
  C4' C5' . 1.345(6) ?
  C5' C6' . 1.416(5) ?
  C6' Cl6B . 1.700(10)
  ?
  N2 C3 . 1.364(3) ?
  C3 C4 . 1.356(4) ?
  C4 C4a . 1.412(4) ?
  C4a C8a . 1.412(4) ?
  C4a C5 . 1.414(4) ?
  C5 C6 . 1.355(4) ?
  C6 C7 . 1.403(5) ?
  C7 C8 . 1.351(4) ?
  C8 C8a . 1.414(4) ?
  C3 C31 . 1.510(4) ?
  C31 O31 . 1.228(3) ?
  C31 N31 . 1.327(4) ?
  N31 C32A . 1.476(8) ?
  N31 C33A . 1.479(7) ?
  N31 C32B . 1.480(10)
  ?
  N31 C33B . 1.540(10)
  ?
  C33A C34A . 1.510(10)
  ?
  C33A C35A . 1.520(10)
  ?
  C35A C36A . 1.530(10)
  ?
  C33B C34B . 1.51(2) ?
  C33B C35B . 1.520(10)
  ?
  C35B C36B . 1.51(2) ?