#------------------------------------------------------------------------------
#$Date: 2008-11-20 19:58:43 +0000 (Thu, 20 Nov 2008) $
#$Revision: 481 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008502.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_2008502
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_publ_section_title
;
(S,S)-Ferrocenyl[methyl(1-phenylethyl)amino]acetonitrile
;
loop_
_publ_author_name
  'Howell, James A. S.'
  'Humphries, Kristina'
  'McArdle, Patrick'
  'Cunningham, Desmond'
  'Walsh, Martin'
  'Daly, Pearl'
_chemical_formula_moiety  'C21 H22 Fe N2'
_chemical_formula_sum  'C21 H22 Fe1 N2'
_chemical_formula_iupac  '[Fe (C5 H5) (C16 H17 N2)]'
_chemical_formula_weight  358.26
_symmetry_cell_setting  Orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y ,z'
  '-x+1/2, -y, z+1/2'
  '-x, y+1/2, -z+1/2'
  'x+1/2, -y+1/2, -z'
_cell_length_a  6.001(3)
_cell_length_b  12.107(4)
_cell_length_c  22.995(5)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  1670.7(11)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.424
_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
  Fe1  .34715(2)  .242602(9)  .177476(5)  .00859(3) Uani d . 1 . . Fe
  N2  .72066(12)  -.00827(6)  .07694(3)  .00998(11) Uani d . 1 . . N
  N1  .32873(17)  .14579(9)  -.00272(4)  .02059(16) Uani d . 1 . . N
  C1  .49387(13)  .10842(6)  .14134(4)  .00928(11) Uani d . 1 . . C
  C2  .26568(15)  .08486(7)  .15493(4)  .01092(12) Uani d . 1 . . C
  H2  .1560  .0637  .1286  .014 Uiso calc R 1 . . H
  C3  .23701(16)  .09965(7)  .21585(4)  .01242(13) Uani d . 1 . . C
  H3  .1050  .0895  .2363  .016 Uiso calc R 1 . . H
  C4  .44523(17)  .13277(7)  .24017(4)  .01347(14) Uani d . 1 . . C
  H4  .4723  .1484  .2791  .018 Uiso calc R 1 . . H
  C5  .60464(15)  .13769(7)  .19423(4)  .01209(13) Uani d . 1 . . C
  H5  .7542  .1566  .1980  .016 Uiso calc R 1 . . H
  C6  .60650(14)  .09784(7)  .08324(4)  .01031(12) Uani d . 1 . . C
  H6  .7221  .1549  .0820  .013 Uiso calc R 1 . . H
  C7  .44556(16)  .12410(7)  .03544(4)  .01368(14) Uani d . 1 . . C
  C8  .83760(17)  -.01688(8)  .02148(4)  .01532(14) Uani d . 1 . . C
  H8A  .7314  -.0158  -.0097  .020 Uiso calc R 1 . . H
  H8B  .9201  -.0848  .0203  .020 Uiso calc R 1 . . H
  H8C  .9383  .0443  .0174  .020 Uiso calc R 1 . . H
  C9  .59366(14)  -.10877(7)  .09249(4)  .01023(12) Uani d . 1 . . C
  H9  .5040  -.0901  .1267  .013 Uiso calc R 1 . . H
  C10  .43135(17)  -.14787(8)  .04573(5)  .01708(16) Uani d . 1 . . C
  H10A  .3369  -.2045  .0614  .022 Uiso calc R 1 . . H
  H10B  .5134  -.1769  .0133  .022 Uiso calc R 1 . . H
  H10C  .3416  -.0868  .0330  .022 Uiso calc R 1 . . H
  C11  .75880(15)  -.19756(6)  .11162(4)  .01011(12) Uani d . 1 . . C
  C12  .73716(19)  -.30808(7)  .09517(4)  .01559(15) Uani d . 1 . . C
  H12  .6176  -.3296  .0721  .020 Uiso calc R 1 . . H
  C13  .8932(2)  -.38663(8)  .11307(5)  .01949(18) Uani d . 1 . . C
  H13  .8773  -.4598  .1015  .025 Uiso calc R 1 . . H
  C14 1.0715(2)  -.35657(8)  .14792(5)  .01918(18) Uani d . 1 . . C
  H14 1.1765  -.4088  .1593  .025 Uiso calc R 1 . . H
  C15 1.09132(16)  -.24684(9)  .16581(4)  .01754(15) Uani d . 1 . . C
  H15 1.2088  -.2260  .1898  .023 Uiso calc R 1 . . H
  C16  .93625(16)  -.16857(7)  .14789(4)  .01349(14) Uani d . 1 . . C
  H16  .9509  -.0958  .1602  .018 Uiso calc R 1 . . H
  C17  .32043(17)  .39323(7)  .21694(5)  .01539(15) Uani d . 1 . . C
  H17  .3491  .4085  .2559  .020 Uiso calc R 1 . . H
  C18  .47767(18)  .39847(7)  .17072(5)  .01783(17) Uani d . 1 . . C
  H18  .6270  .4180  .1741  .023 Uiso calc R 1 . . H
  C19  .3662(2)  .36852(8)  .11835(5)  .02131(19) Uani d . 1 . . C
  H19  .4300  .3649  .0815  .028 Uiso calc R 1 . . H
  C20  .1392(2)  .34506(8)  .13237(5)  .02006(18) Uani d . 1 . . C
  H20  .0288  .3235  .1064  .026 Uiso calc R 1 . . H
  C21  .11256(16)  .36065(7)  .19327(5)  .01625(16) Uani d . 1 . . C
  H21  -.0190  .3511  .2140  .021 Uiso calc R 1 . . 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
  Fe1  .01163(5)  .00448(4)  .00967(4)  .00215(3)  -.00234(4)  .00056(3)
  N2  .0096(3)  .0086(2)  .0118(3)  .0019(2)  .0024(2)  .00173(19)
  N1  .0189(4)  .0261(4)  .0167(4)  .0039(3)  -.0022(3)  .0064(3)
  C1  .0105(3)  .0064(2)  .0109(3)  .0017(2)  -.0014(2)  .0001(2)
  C2  .0117(3)  .0078(3)  .0133(3)  .0002(2)  -.0010(2)  -.0010(2)
  C3  .0163(3)  .0091(3)  .0119(3)  .0005(2)  .0006(3)  .0014(2)
  C4  .0197(4)  .0104(3)  .0103(3)  .0034(3)  -.0036(3)  .0018(2)
  C5  .0129(3)  .0092(3)  .0142(3)  .0029(2)  -.0049(2)  .0006(2)
  C6  .0105(3)  .0083(3)  .0122(3)  .0013(2)  -.0001(2)  .0019(2)
  C7  .0138(3)  .0137(3)  .0136(3)  .0025(2)  .0007(3)  .0029(2)
  C8  .0125(3)  .0186(3)  .0149(3)  .0025(3)  .0052(3)  .0030(3)
  C9  .0102(3)  .0084(3)  .0122(3)  .0008(2)  .0021(2)  -.0004(2)
  C10  .0148(4)  .0145(3)  .0220(4)  -.0006(3)  -.0049(3)  -.0010(3)
  C11  .0132(3)  .0078(3)  .0094(3)  .0019(2)  .0023(2)  -.0002(2)
  C12  .0226(4)  .0092(3)  .0150(4)  .0029(3)  -.0004(3)  -.0016(3)
  C13  .0293(5)  .0091(3)  .0201(4)  .0058(3)  .0015(3)  .0010(3)
  C14  .0228(4)  .0142(4)  .0206(4)  .0076(3)  .0022(3)  .0068(3)
  C15  .0176(3)  .0164(4)  .0186(4)  .0034(3)  -.0019(3)  .0057(3)
  C16  .0152(4)  .0102(3)  .0150(4)  .0019(2)  -.0010(3)  .0015(2)
  C17  .0211(4)  .0075(3)  .0176(4)  .0014(3)  -.0024(3)  -.0023(2)
  C18  .0191(4)  .0081(3)  .0263(5)  .0003(2)  .0019(3)  .0036(3)
  C19  .0361(6)  .0114(3)  .0165(4)  .0076(4)  .0031(4)  .0058(3)
  C20  .0268(5)  .0117(3)  .0218(4)  .0068(3)  -.0125(4)  .0011(3)
  C21  .0145(4)  .0100(3)  .0243(4)  .0044(2)  -.0013(3)  .0000(3)
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
  Fe1 C1 . 2.0260(9) ?
  Fe1 C5 . 2.0369(10) ?
  Fe1 C2 . 2.0384(10) ?
  Fe1 C21 . 2.0387(11) ?
  Fe1 C20 . 2.0424(10) ?
  Fe1 C17 . 2.0432(10) ?
  Fe1 C19 . 2.0460(10) ?
  Fe1 C4 . 2.0477(9) ?
  Fe1 C18 . 2.0491(11) ?
  Fe1 C3 . 2.0521(10) ?
  N2 C8 . 1.4593(12) ?
  N2 C6 . 1.4631(12) ?
  N2 C9 . 1.4796(11) ?
  N1 C7 . 1.1534(13) ?
  C1 C5 . 1.4306(13) ?
  C1 C2 . 1.4332(14) ?
  C1 C6 . 1.5028(13) ?
  C2 C3 . 1.4227(14) ?
  C3 C4 . 1.4265(15) ?
  C4 C5 . 1.4263(14) ?
  C6 C7 . 1.4974(13) ?
  C9 C10 . 1.5260(14) ?
  C9 C11 . 1.5268(12) ?
  C11 C12 . 1.3965(13) ?
  C11 C16 . 1.3974(14) ?
  C12 C13 . 1.3968(15) ?
  C13 C14 . 1.3851(18) ?
  C14 C15 . 1.3958(16) ?
  C15 C16 . 1.3906(13) ?
  C17 C21 . 1.4170(15) ?
  C17 C18 . 1.4226(16) ?
  C18 C19 . 1.4245(17) ?
  C19 C20 . 1.4285(19) ?
  C20 C21 . 1.4221(17) ?