#------------------------------------------------------------------------------
#$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2200319.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_2200319
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2001
_journal_volume  57
_journal_page_first  o511
_journal_page_last  o513
_publ_section_title
;
7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine-4-ylamine,
an lck tyrosine kinase inhibitor
;
loop_
_publ_author_name
  "Zrinka Bani\'c Tomi\<si\'c"
  'Andreja \<Cempuh'
  'Ivica Malnar'
_chemical_formula_moiety  'C23 H22 N4 O'
_chemical_formula_sum  'C23 H22 N4 O'
_chemical_formula_iupac  'C23 H22 N4 O'
_chemical_formula_weight  370.45
_symmetry_cell_setting  Orthorhombic
_symmetry_space_group_name_H-M  'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
  x,y,z
  1/2-x,-y,1/2+z
  1/2+x,1/2-y,-z
  -x,1/2+y,1/2-z
  -x,-y,-z
  1/2+x,y,1/2-z
  1/2-x,1/2+y,z
  x,1/2-y,1/2+z
_cell_length_a  11.914(2)
_cell_length_b  12.399(5)
_cell_length_c  26.133(5)
_cell_angle_alpha  90
_cell_angle_beta  90
_cell_angle_gamma  90
_cell_volume  3860.4(18)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.275
_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_thermal_displace_type
_atom_site_occupancy
_atom_site_type_symbol
  O16  .2541(4)  -.1436(4)  .68577(16)  .0727(19) Uani 1.000 O
  N1  -.2088(4)  .3298(3)  .52631(17)  .0390(17) Uani 1.000 N
  N3  -.2389(4)  .1407(4)  .51220(18)  .0440(17) Uani 1.000 N
  N7  -.0508(4)  .3681(4)  .58142(18)  .0433(19) Uani 1.000 N
  N41  -.1340(4)  .0086(3)  .54859(15)  .051(2) Uani 1.000 N
  C2  -.2611(4)  .2454(5)  .5062(2)  .049(2) Uani 1.000 C
  C4  -.1503(5)  .1147(5)  .5410(2)  .035(2) Uani 1.000 C
  C5  .0086(5)  .2000(5)  .5984(2)  .038(3) Uani 1.000 C
  C6  .0265(4)  .3071(5)  .6072(2)  .043(3) Uani 1.000 C
  C8  -.1191(5)  .2997(5)  .5546(2)  .037(2) Uani 1.000 C
  C9  -.0834(5)  .1944(5)  .5634(2)  .033(2) Uani 1.000 C
  C10  .0740(5)  .1104(5)  .6210(2)  .035(2) Uani 1.000 C
  C11  .1189(4)  .0271(4)  .5922(2)  .041(2) Uani 1.000 C
  C12  .1759(4)  -.0555(5)  .6151(2)  .042(2) Uani 1.000 C
  C13  .1929(5)  -.0577(5)  .6675(3)  .047(3) Uani 1.000 C
  C14  .1537(5)  .0264(5)  .6967(2)  .053(3) Uani 1.000 C
  C15  .0930(5)  .1086(4)  .6737(2)  .047(3) Uani 1.000 C
  C17  .2673(6)  -.1556(5)  .7384(3)  .048(3) Uani 1.000 C
  C18  .2003(6)  -.2244(6)  .7635(3)  .063(3) Uani 1.000 C
  C19  .2193(6)  -.2440(6)  .8148(3)  .073(3) Uani 1.000 C
  C20  .3041(7)  -.1921(6)  .8393(3)  .071(3) Uani 1.000 C
  C21  .3716(6)  -.1223(6)  .8139(3)  .083(4) Uani 1.000 C
  C22  .3536(7)  -.1054(6)  .7630(3)  .077(4) Uani 1.000 C
  C71  -.0632(5)  .4861(4)  .5846(2)  .051(3) Uani 1.000 C
  C72  -.0838(6)  .5261(5)  .6392(2)  .078(3) Uani 1.000 C
  C73  .0152(7)  .5947(6)  .6527(3)  .093(4) Uani 1.000 C
  C74  .0557(6)  .6381(6)  .6025(3)  .095(4) Uani 1.000 C
  C75  .0411(5)  .5452(5)  .5660(2)  .063(3) Uani 1.000 C
  H2  -.32160  .26140  .48500  .0580 Uiso 1.000 H
  H6  .08320  .33470  .62790  .0520 Uiso 1.000 H
  H11  .11000  .02730  .55690  .0490 Uiso 1.000 H
  H12  .20390  -.11140  .59500  .0510 Uiso 1.000 H
  H14  .16790  .02830  .73170  .0640 Uiso 1.000 H
  H15  .06410  .16380  .69390  .0570 Uiso 1.000 H
  H18  .14160  -.25860  .74660  .0750 Uiso 1.000 H
  H19  .17430  -.29260  .83250  .0870 Uiso 1.000 H
  H20  .31600  -.20450  .87390  .0860 Uiso 1.000 H
  H21  .42910  -.08650  .83090  .1000 Uiso 1.000 H
  H22  .40070  -.05930  .74490  .0930 Uiso 1.000 H
  H41A  -.17920  -.03740  .53520  .0600 Uiso 1.000 H
  H41B  -.07830  -.01310  .56680  .0600 Uiso 1.000 H
  H71  -.12690  .50780  .56320  .0600 Uiso 1.000 H
  H72A  -.15250  .56790  .64090  .0940 Uiso 1.000 H
  H72B  -.08990  .46570  .66260  .0940 Uiso 1.000 H
  H73A  .07310  .55210  .66910  .1110 Uiso 1.000 H
  H73B  -.00670  .65280  .67540  .1110 Uiso 1.000 H
  H74A  .13380  .65970  .60460  .1140 Uiso 1.000 H
  H74B  .01120  .69970  .59180  .1140 Uiso 1.000 H
  H75A  .10610  .49810  .56690  .0750 Uiso 1.000 H
  H75B  .03080  .57110  .53130  .0750 Uiso 1.000 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
  O16  .093(4)  .080(3)  .045(3)  .044(3)  -.003(3)  .006(3)
  N1  .036(3)  .039(3)  .042(3)  .003(3)  -.002(3)  -.006(3)
  N3  .043(3)  .032(3)  .057(3)  .000(3)  -.017(3)  .000(3)
  N7  .043(3)  .027(3)  .060(4)  .003(3)  -.011(3)  -.004(3)
  N41  .054(4)  .029(3)  .069(4)  -.007(3)  -.016(3)  -.003(3)
  C2  .042(4)  .051(4)  .053(4)  .006(4)  -.008(4)  .001(4)
  C4  .045(4)  .028(4)  .033(4)  -.005(4)  .011(3)  .002(3)
  C5  .047(5)  .033(4)  .034(4)  .003(4)  .002(3)  .003(4)
  C6  .031(4)  .052(5)  .046(4)  -.007(4)  -.006(3)  -.009(4)
  C8  .039(4)  .033(4)  .038(4)  -.011(4)  .001(4)  .000(4)
  C9  .038(4)  .029(4)  .031(4)  -.004(4)  .002(3)  -.004(3)
  C10  .033(4)  .040(4)  .033(4)  -.005(4)  .001(3)  .001(4)
  C11  .031(4)  .048(4)  .044(4)  .005(3)  -.007(3)  .007(4)
  C12  .046(4)  .050(4)  .031(4)  .003(4)  .005(4)  -.008(4)
  C13  .044(5)  .051(5)  .046(5)  .007(4)  .001(4)  .000(4)
  C14  .058(5)  .063(5)  .038(4)  .014(4)  -.001(4)  -.009(4)
  C15  .044(5)  .044(4)  .054(5)  .016(4)  .004(4)  -.008(4)
  C17  .060(6)  .042(4)  .042(5)  .025(4)  .005(5)  .010(4)
  C18  .058(5)  .077(6)  .053(5)  .001(5)  .000(4)  .004(5)
  C19  .063(6)  .084(6)  .072(6)  .000(5)  .023(5)  .027(5)
  C20  .063(6)  .095(6)  .055(5)  .037(5)  -.007(5)  .015(5)
  C21  .077(7)  .106(7)  .066(6)  -.013(5)  -.005(5)  .002(6)
  C22  .086(7)  .084(6)  .062(6)  -.024(5)  .010(5)  .013(5)
  C71  .053(5)  .031(4)  .068(5)  -.001(4)  -.012(4)  -.003(4)
  C72  .113(7)  .046(5)  .076(6)  -.008(5)  .033(6)  -.020(4)
  C73  .099(7)  .079(6)  .100(7)  .020(5)  -.038(6)  -.030(6)
  C74  .091(6)  .065(6)  .129(8)  -.027(5)  .006(6)  -.033(6)
  C75  .071(5)  .047(4)  .070(5)  -.016(4)  .009(5)  -.001(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  O16 C13 . . 1.376(8) no
  O16 C17 . . 1.392(9) no
  N1 C2 . . 1.326(7) no
  N1 C8 . . 1.352(7) no
  N3 C2 . . 1.334(8) no
  N3 C4 . . 1.336(7) no
  N7 C6 . . 1.369(7) no
  N7 C8 . . 1.368(8) no
  N7 C71 . . 1.473(7) no
  N41 C4 . . 1.345(7) no
  N41 H41A . .  .8589 no
  N41 H41B . .  .8598 no
  C4 C9 . . 1.398(8) no
  C5 C9 . . 1.429(8) no
  C5 C10 . . 1.480(8) no
  C5 C6 . . 1.364(9) no
  C8 C9 . . 1.392(9) no
  C10 C15 . . 1.396(7) no
  C10 C11 . . 1.385(8) no
  C11 C12 . . 1.367(8) no
  C12 C13 . . 1.385(9) no
  C13 C14 . . 1.374(9) no
  C14 C15 . . 1.387(8) no
  C17 C18 . . 1.340(10) no
  C17 C22 . . 1.363(11) no
  C18 C19 . . 1.381(11) no
  C19 C20 . . 1.358(11) no
  C20 C21 . . 1.355(11) no
  C21 C22 . . 1.364(11) no
  C71 C75 . . 1.522(8) no
  C71 C72 . . 1.530(8) no
  C72 C73 . . 1.496(11) no
  C73 C74 . . 1.498(11) no
  C74 C75 . . 1.506(10) no
  C2 H2 . .  .9305 no
  C6 H6 . .  .9306 no
  C11 H11 . .  .9286 no
  C12 H12 . .  .9314 no
  C14 H14 . .  .9305 no
  C15 H15 . .  .9304 no
  C18 H18 . .  .9295 no
  C19 H19 . .  .9298 no
  C20 H20 . .  .9281 no
  C21 H21 . .  .9294 no
  C22 H22 . .  .9302 no
  C71 H71 . .  .9804 no
  C72 H72A . .  .9698 no
  C72 H72B . .  .9696 no
  C73 H73A . .  .9688 no
  C73 H73B . .  .9690 no
  C74 H74A . .  .9698 no
  C74 H74B . .  .9709 no
  C75 H75A . .  .9702 no
  C75 H75B . .  .9698 no