##############################################################################
###                                                                        ###
###           Electronic papers (Acta Crystallographica Section C)         ###
###                                                                        ###
##############################################################################
#                                                                            #
# This paper is published electronically. It meets the data-validation       #
# criteria for publication in Acta Crystallographica Section C.              #
# The submission has been checked by a Section C Co-editor though the text   #
# in _publ_section_comments is the responsibility of the authors.            #
#                                                                            #
# Electronic papers are listed in the printed contents pages of an issue of  #
# Acta Crystallographica Section C within two months of acceptance and are   #
# available by email and via the online contents pages for that issue.       #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     IUC0000064
_journal_date_recd_electronic     2000-02-21
_journal_date_accepted     2000-03-03
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2000
_journal_volume     56
_journal_issue      4
_journal_page_first     e130
_journal_page_last     e131
_journal_paper_category     CM
_publ_contact_author_name     'Prof. Hoong-Kun Fun'
_publ_contact_author_address
;
X-ray Crystallography Unit
School of Physics
Universiti Sains Malaysia
11800 USM
Penang
MALAYSIA
;
_publ_contact_author_email     hkfun@usm.my
_publ_contact_author_fax     '6 04 6579150'
_publ_contact_author_phone     '6 04 6577888  Ext. 3690'
_publ_section_title
;
Tris(8-quinolinolato-N,O)cobalt(III) ethanol solvate
;
loop_
    _publ_author_name
    _publ_author_address
    'Shanmuga Sundara Raj, S.'
;
X-ray Crystallography Unit
School of Physics
Universiti Sains Malaysia
11800 USM
Penang
Malaysia
;
    'Razak, Ibrahim Abdul'
;
X-ray Crystallography Unit
School of Physics
Universiti Sains Malaysia
11800 USM
Penang
Malaysia
;
    'Fun, Hoong-Kun'
;
X-ray Crystallography Unit
School of Physics
Universiti Sains Malaysia
11800 USM
Penang
Malaysia
;
    'Zhao, PuSu'
;
Materials Chemistry Laboratory
Nanjing University of Science & Technology
Nanjing
210094
People's Republic of China
;
    'Jian, Fangfang'
;
Materials Chemistry Laboratory
Nanjing University of Science & Technology
Nanjing
210094
People's Republic of China
;
    'Yang, Xujie'
;
Materials Chemistry Laboratory
Nanjing University of Science & Technology
Nanjing
210094
People's Republic of China
;
    'Lu, Lude'
;
Materials Chemistry Laboratory
Nanjing University of Science & Technology
Nanjing
210094
People's Republic of China
;
    'Wang, Xin'
;
Materials Chemistry Laboratory
Nanjing University of Science & Technology
Nanjing
210094
People's Republic of China
;
_publ_section_synopsis
;
The central Co atom of the title complex has a distorted octahedral
coordination. The three Co---O bond distances are in the range
1.887(2)--1.910(2)Å, while the three Co---N bond distances are in the
range 1.919(2)--1.934(2)Å. The ethanol solvate molecule is involved
in an O---H...O intermolecular hydrogen bond.
;
_publ_section_abstract
;
In the crystal of the title complex, [Co(C₉H₆NO)₃].C₂H₅OH,
the central Co atom  has a distorted octahedral coordination comprising
of three N atoms and three O atoms from the three 8-quinolinolato ligands.
The three Co---O bond distances are in the range 1.887(2)--1.910(2)Å, while
the three Co---N bond distances range from 1.919(2) to 1.934(2)Å. The solvent
ethanol molecule forms an intermolecular O---H...O hydrogen bonding
with a quinolinolato ligand.
;
_publ_section_comment
;
8-Quinolinol has been widely used as an extracting agent for transition
metals and for the fluorescence analysis of group 3A elements as well
as in the preparation of non-linear optical materials with second
harmonic generation at high intensity and stability at room temperature
(Sanz-Medel et al., 1987; Sugiyama et al., 1991; Kato et al., 1988).
Its complexes with transition metals have also found extensive applications.
For example, bis(8-quinolinolato-N,O)nickel(II) [NiQ₂] has been used as
a free-resistant additive for olefin polymers and as a fungicide for leather
(Uma & Krishnamurthi, 1984). Also, tri(8-quinolinolato)cobalt(III) has
been synthesized and used to assist in the metal--ligand assignments which
are further based on Zn labeling of the Zn complex and on the effects of
metal ion substitution in relation to expectations based on crystal field
theory (Nakamoto & Ohkaku, 1971). Although the synthesis and characterization
of the title complex, (I), have been discussed previously (Hollingshead, 1954;
Engelter et al., 1989; Cheng, 1983), its crystal structure, to our
knowledge, has not been reported.
In the 8-quinolinato ligands, the absence of any unusually
long bonds and the marginally longer  carbonyl bonds (C1---O1 = 1.325(4)Å;
C10---O2 = 1.337(3)Å and C19---O3 = 1.313(4)Å versus 1.28Å),
shorter than the normal single bond in ether and alcohols (>1.4Å),
suggest that the delocalization extends over the entire molecule and will
therefore withdraw more negative charge from the cation (Barton et al., 1983).
The three 8-quinolinol ligands are coordinated to the central Co atom by
their O and N atoms, forming five-membered chelate rings. The
CoIII atom has a slightly distorted octahedral coordination.
The structure of the title complex is very similar to that of
tris(8-quinolinolate)chromium(III) (CrQ₃; Folting et al., 1968) and
tris(8-quinolinolate)manganese(III) (MnQ₃; Xiong & You, 1995).
The Co---O bond distances in CoQ₃ [1.887(2), 1.903(2) and
1.910(2)Å] are normal,  slighty shorter than those in
Co(C₅H₄NOS)₃ [1.943(7)Å; Xu et al., 1995], and are in agreement
with those of [Co(salpron)(py)]³ [1.890(4)Å; Zhu et al., 1996]. Similarly,
the Co---N bond distances [1.919(2), 1.931(2) and 1.934(2)Å] are somewhat
shorter than those in [Co(phen)(pro)₂]⁺ [1.948(3)Å; Ye et al., 1994]
and [Co(C₄H₉(salen)(py)] [1.967(5)Å; Zhu et al., 1996].
The mean chelate angles Co---O---C and Co---N---C [111.5(2) and 110.3(2)°,
respectively] and the mean bite angle O---Co---N of 85.7(1)° are close to
those metal complexes of 8-hydroxyquinoline reported (Xiong & You,
1995; Xiong et al., 1995; Folting et al., 1968).
The three chelate rings, Co1/O1/C1/C9/N1, Co1/O2/C10/C18/N2 and
Co1/O3/C19/C27/N3 make dihedral angles of 87.1(1), 86.9(1) and 88.1(1)°,
respectively, with each other. Sterochemistry explains that this cis
geometry of the ligands minimizes the stereochemical interference
between the H atoms in the 2 and 4 positions of different ring systems.
The ethanol molecules do not take part in the coordination but invloves in
an O---H...O intermolecular hydrogen bond with one of the ligands; the donor
and acceptor distance, O4...O2, is 2.777(4)Å. The molecular packing is
stabilized by C---H...O and C---H...π(Cg) interactions (Table 2).
;
_publ_section_acknowledgements
;
The authors would like to thank the Malaysian Government and Universiti
Sains Malaysia for research grant R&D No. 305/pfizik/622004. SSSR thanks the
Universiti Sains Malaysia for a Visiting Postdoctoral Fellowship.
;
_publ_section_references
;
Barton, R .J., Dabeka, R. W., Shengzhi, H., Mihichuk, L. M., Pizzey, M.,
Robertson, B. E. & Wallace, W. J. (1983). Acta Cryst. C39, 714-717.
Cheng, W. (1983). J. Coord. Chem. 13, 57-62.
Engelter, C., Jackson, G., Knight, C. & Thornton, D. A. (1989). J.
Mol. Struct. 213, 133-144.
Folting, K., Cox, M. M., Moore, J. W. & Merritt, J. L. L. (1968). Chem.
Commun. pp. 1170-1171.
Hollingshead, R. G. W. (1954). In Oxine and its Derivatives, Vols. I-IV.
London: Butterworths.
Kato, H., Kanemitsuya, K. & Futagami, T. (1988). Jpn Kokai Tokkyo Koho JP
63 128 041 [88 128 041].
Nakamoto, K. & Ohkahu, N. (1971). Inorg. Chem. 10, 798-805.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.
Sanz-Medel, A., Fernandez, C. R. & Garcia, A. J. I. (1987). Analyst, 11,
493-497.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G.M. (1997).  SHELXTL Software Reference Manual. Version 5.1.
Bruker AXS Inc., Madison, Wisconsin, USA.
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc.,
Madison, Wisconsin, USA.
Spek, A.L. (1990). Acta Cryst. A46, C-34.
Sugiyama, T., Shigemoto, T., Kamiya, M. & Ota, T. (1991). Jpn Kokai
Tokkyo Koho JP 02 262 627 [90 262 67].
Uma, L. & Krishnamurthi, V.S. (1984). Leather Sci. 31, 15-16.
Xiong, R. G. & You, X. Z. (1995). Acta Cryst. C51, 1978-1980.
Xiong, R. G., Zou, J. L., You, X. Z., Wu, Q. J. &  Huang, X. Y. (1995).
Transition Met. Chem. 20, 498-500.
Xu, Y. J., Kang, B. S., Chen, X. T. & Huang, L. R. (1995).
Acta Cryst. C51, 370-374.
Ye, B. H., Chen, X. M., Zeng, T. X. & Ji, L. N. (1994). Polyhedron, 14,
2185-2191.
Zhu, D. R., You, X. Z., Shi, X. H., Fun, H. K. & Sivakumar, K. (1996). Acta
Cryst. C52, 1146-1148.
;
_publ_section_exptl_prep
;
The title complex was prepared by mixing an aqueous solution of cobalt(II)
acetate and 8-hydroxyquinoline with heating. The complex was collected by
filtration, washed with water and dried over a night. The deep red single
crystals suitable for X-ray analysis were obtained by recrystalization
from anhydrous ethanol solution.
;
_publ_section_exptl_refinement
;
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
tris(8-quinolinolato-N,O)Cobalt(III) Ethanol Solvate
;
_chemical_name_common     ?
_chemical_formula_moiety     ?
_chemical_formula_sum     'C29 H24 Co N3 O4'
_chemical_formula_iupac     '[Co (C9 H6 N O)3], C2 H6 O'
_chemical_formula_weight     537.44
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     11.26490(10)
_cell_length_b     13.1101(2)
_cell_length_c     16.6181(3)
_cell_angle_alpha     90.00
_cell_angle_beta     94.2249(3)
_cell_angle_gamma     90.00
_cell_volume     2447.56(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6862
_cell_measurement_theta_min     1.98
_cell_measurement_theta_max     28.31
_cell_measurement_temperature     293(2)
_exptl_crystal_description     slab
_exptl_crystal_colour     black
_exptl_crystal_size_max      .38
_exptl_crystal_size_mid      .22
_exptl_crystal_size_min      .12
_exptl_crystal_density_diffrn     1.459
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1112
_exptl_absorpt_coefficient_mu      .743
_exptl_absorpt_correction_type     empirical
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min      .765
_exptl_absorpt_correction_T_max      .916
_exptl_special_details
;
The data collection covered over a hemisphere of reciprocal space by a
combination of three sets of exposures; each set had a different φ angle (0,
88 and 180°) for the crystal and each exposure of 10s covered 0.3° in ω.
The crystal-to-detector distance was 4 cm and the detector swing angle was
-35°. Coverage of the unique set is over 99% complete. Crystal decay was
monitored by repeating fifty initial frames at the end of data collection
and analysing the duplicate reflections, and was found  to be negligible.
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Siemens SMART CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     8.33
_diffrn_reflns_number     16823
_diffrn_reflns_av_R_equivalents      .069
_diffrn_reflns_av_sigmaI/netI      .0858
_diffrn_reflns_theta_min     1.98
_diffrn_reflns_theta_max     28.27
_diffrn_reflns_theta_full     28.27
_diffrn_measured_fraction_theta_max      .983
_diffrn_measured_fraction_theta_full      .983
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_k_max     17
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     5957
_reflns_number_gt     3727
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .102
_refine_ls_R_factor_gt      .055
_refine_ls_wR_factor_ref      .147
_refine_ls_goodness_of_fit_ref      .973
_refine_ls_restrained_S_all      .973
_refine_ls_number_reflns     5957
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
             'calc w = 1/[σ²(Fo²)+(0.0709P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_shift/su_max     <0.001
_refine_ls_shift/su_mean      .000
_refine_diff_density_max      .558
_refine_diff_density_min      -.767
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C'  .0033  .0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H'  .0000  .0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N'  .0061  .0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O'  .0106  .0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Co' 'Co'  .3494  .9721
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Siemens, 1996)'
_computing_cell_refinement     'SAINT (Siemens, 1996)'
_computing_data_reduction     SAINT
_computing_structure_solution     'SHELXTL (Sheldrick, 1997)'
_computing_structure_refinement     SHELXTL
_computing_molecular_graphics     ?
_computing_publication_material
                       'SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990)'
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
    Co1  .43457(4)  .48233(3)  .24446(2)  .02880(14) Uani d . 1 . . Co
    O1  .60063(19)  .48624(15)  .23028(12)  .0341(5) Uani d . 1 . . O
    O2  .26970(19)  .48312(16)  .26418(12)  .0355(5) Uani d . 1 . . O
    O3  .4288(2)  .34339(15)  .21476(12)  .0384(5) Uani d . 1 . . O
    N1  .4524(2)  .62417(19)  .27415(14)  .0297(5) Uani d . 1 . . N
    N2  .4612(2)  .43695(19)  .35408(14)  .0334(6) Uani d . 1 . . N
    N3  .3944(2)  .51022(19)  .13143(14)  .0314(6) Uani d . 1 . . N
    C1  .6477(3)  .5763(2)  .24959(17)  .0325(7) Uani d . 1 . . C
    C2  .7673(3)  .6014(3)  .2492(2)  .0430(8) Uani d . 1 . . C
    H2A  .8222  .5520  .2365  .052 Uiso calc R 1 . . H
    C3  .8059(3)  .7008(3)  .2676(2)  .0503(9) Uani d . 1 . . C
    H3A  .8865  .7160  .2669  .060 Uiso calc R 1 . . H
    C4  .7285(3)  .7765(3)  .2868(2)  .0505(9) Uani d . 1 . . C
    H4A  .7567  .8421  .2975  .061 Uiso calc R 1 . . H
    C5  .6072(3)  .7548(2)  .29042(18)  .0384(8) Uani d . 1 . . C
    C6  .5181(3)  .8238(3)  .3100(2)  .0485(9) Uani d . 1 . . C
    H6A  .5382  .8913  .3218  .058 Uiso calc R 1 . . H
    C7  .4030(3)  .7933(3)  .3121(2)  .0483(9) Uani d . 1 . . C
    H7A  .3452  .8395  .3259  .058 Uiso calc R 1 . . H
    C8  .3715(3)  .6919(2)  .29323(18)  .0379(7) Uani d . 1 . . C
    H8A  .2924  .6718  .2942  .046 Uiso calc R 1 . . H
    C9  .5689(3)  .6542(2)  .27146(16)  .0300(7) Uani d . 1 . . C
    C10  .2528(3)  .4524(2)  .33918(18)  .0349(7) Uani d . 1 . . C
    C11  .1441(3)  .4455(3)  .3718(2)  .0488(9) Uani d . 1 . . C
    H11A  .0747  .4629  .3411  .059 Uiso calc R 1 . . H
    C12  .1387(4)  .4121(3)  .4516(2)  .0617(11) Uani d . 1 . . C
    H12A  .0647  .4089  .4728  .074 Uiso calc R 1 . . H
    C13  .2368(4)  .3842(3)  .4995(2)  .0599(11) Uani d . 1 . . C
    H13A  .2290  .3616  .5519  .072 Uiso calc R 1 . . H
    C14  .3507(3)  .3898(3)  .46889(19)  .0445(9) Uani d . 1 . . C
    C15  .4598(4)  .3634(3)  .5099(2)  .0529(10) Uani d . 1 . . C
    H15A  .4613  .3397  .5627  .064 Uiso calc R 1 . . H
    C16  .5623(4)  .3720(3)  .4735(2)  .0571(10) Uani d . 1 . . C
    H16A  .6335  .3526  .5011  .069 Uiso calc R 1 . . H
    C17  .5630(3)  .4098(3)  .39475(19)  .0447(9) Uani d . 1 . . C
    H17A  .6346  .4160  .3707  .054 Uiso calc R 1 . . H
    C18  .3558(3)  .4260(2)  .38872(18)  .0347(7) Uani d . 1 . . C
    C19  .4038(3)  .3311(2)  .13693(18)  .0340(7) Uani d . 1 . . C
    C20  .3965(3)  .2376(3)  .0978(2)  .0423(8) Uani d . 1 . . C
    H20A  .4116  .1776  .1266  .051 Uiso calc R 1 . . H
    C21  .3663(3)  .2342(3)  .0145(2)  .0501(9) Uani d . 1 . . C
    H21A  .3617  .1710  -.0109  .060 Uiso calc R 1 . . H
    C22  .3433(3)  .3197(3)  -.0309(2)  .0524(10) Uani d . 1 . . C
    H22A  .3221  .3141  -.0859  .063 Uiso calc R 1 . . H
    C23  .3518(3)  .4166(3)  .00591(19)  .0397(8) Uani d . 1 . . C
    C24  .3355(3)  .5116(3)  -.0341(2)  .0471(9) Uani d . 1 . . C
    H24A  .3157  .5136  -.0894  .057 Uiso calc R 1 . . H
    C25  .3491(3)  .6003(3)  .0087(2)  .0469(9) Uani d . 1 . . C
    H25A  .3385  .6627  -.0175  .056 Uiso calc R 1 . . H
    C26  .3788(3)  .5975(3)  .09151(18)  .0376(7) Uani d . 1 . . C
    H26A  .3879  .6586  .1197  .045 Uiso calc R 1 . . H
    C27  .3821(3)  .4202(2)  .08965(17)  .0312(7) Uani d . 1 . . C
    O4  .0598(3)  .5801(3)  .2098(2)  .0969(12) Uani d . 1 . . O
    H4B  .0971  .5272  .2042  .145 Uiso calc R 1 . . H
    C28  .0661(5)  .6411(5)  .1414(4)  .108(2) Uani d . 1 . . C
    H28A  .1489  .6570  .1348  .130 Uiso calc R 1 . . H
    H28B  .0249  .7048  .1497  .130 Uiso calc R 1 . . H
    C29  .0159(8)  .5944(5)  .0696(4)  .172(4) Uani d . 1 . . C
    H29A  .0223  .6400  .0249  .258 Uiso calc R 1 . . H
    H29B  -.0665  .5794  .0754  .258 Uiso calc R 1 . . H
    H29C  .0578  .5323  .0601  .258 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
    Co1  .0303(2)  .0293(2)  .0264(2)  -.00100(18)  -.00034(16)  .00050(17)
    O1  .0324(11)  .0346(11)  .0356(11)  .0024(10)  .0038(10)  -.0029(9)
    O2  .0323(11)  .0439(12)  .0298(11)  -.0045(10)  .0000(9)  .0055(9)
    O3  .0515(14)  .0308(12)  .0320(11)  -.0029(10)  -.0022(10)  .0018(9)
    N1  .0295(13)  .0340(14)  .0255(12)  .0009(11)  .0008(10)  .0030(11)
    N2  .0394(15)  .0299(14)  .0301(13)  .0012(12)  -.0027(12)  -.0009(11)
    N3  .0289(13)  .0367(14)  .0284(13)  .0003(11)  .0015(11)  .0006(11)
    C1  .0330(16)  .0371(18)  .0272(15)  -.0030(14)  .0008(13)  .0023(13)
    C2  .0291(17)  .060(2)  .0407(19)  .0028(16)  .0046(15)  -.0005(16)
    C3  .0339(19)  .067(3)  .049(2)  -.0175(19)  -.0011(17)  .0040(19)
    C4  .053(2)  .050(2)  .048(2)  -.0205(19)  .0019(18)  -.0012(17)
    C5  .045(2)  .0378(18)  .0313(17)  -.0075(15)  -.0024(15)  .0030(14)
    C6  .065(3)  .0282(18)  .052(2)  .0002(17)  .0021(19)  .0007(15)
    C7  .056(2)  .0371(19)  .053(2)  .0123(17)  .0085(19)  -.0032(16)
    C8  .0333(17)  .0410(19)  .0393(18)  .0067(15)  .0012(15)  .0003(14)
    C9  .0316(16)  .0332(16)  .0251(15)  -.0021(13)  .0023(13)  .0032(12)
    C10  .0409(18)  .0315(16)  .0325(16)  -.0079(14)  .0043(14)  -.0011(13)
    C11  .0366(19)  .056(2)  .055(2)  -.0062(17)  .0103(17)  .0029(18)
    C12  .060(3)  .072(3)  .057(3)  -.021(2)  .028(2)  -.005(2)
    C13  .085(3)  .059(2)  .038(2)  -.016(2)  .020(2)  .0045(18)
    C14  .066(2)  .0376(18)  .0306(17)  -.0074(17)  .0065(17)  .0000(14)
    C15  .075(3)  .051(2)  .0307(19)  .002(2)  -.0072(19)  .0077(16)
    C16  .073(3)  .055(2)  .040(2)  .015(2)  -.020(2)  .0047(18)
    C17  .048(2)  .047(2)  .0374(19)  .0065(16)  -.0113(16)  .0021(15)
    C18  .0460(19)  .0303(17)  .0276(15)  -.0039(14)  .0013(14)  .0008(12)
    C19  .0287(16)  .0385(18)  .0346(17)  -.0027(14)  .0012(14)  -.0045(14)
    C20  .0402(19)  .0387(19)  .048(2)  -.0009(15)  .0010(16)  -.0097(15)
    C21  .044(2)  .050(2)  .056(2)  .0000(17)  .0018(18)  -.0232(18)
    C22  .050(2)  .071(3)  .0354(19)  .000(2)  -.0021(17)  -.0189(18)
    C23  .0326(17)  .054(2)  .0318(17)  .0014(15)  .0001(14)  -.0054(15)
    C24  .048(2)  .066(2)  .0263(16)  .0032(18)  -.0036(15)  .0051(16)
    C25  .049(2)  .055(2)  .0355(19)  .0046(18)  .0018(17)  .0136(16)
    C26  .0415(19)  .0387(18)  .0325(17)  -.0005(15)  .0019(15)  .0048(14)
    C27  .0274(15)  .0400(18)  .0261(15)  -.0015(13)  .0009(13)  -.0048(13)
    O4  .074(2)  .103(3)  .115(3)  .020(2)  .013(2)  .043(2)
    C28  .095(4)  .103(5)  .129(5)  .015(3)  .027(4)  .056(4)
    C29  .313(12)  .117(6)  .083(5)  -.057(6)  -.007(6)  -.008(4)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    Co1 O3 . 1.887(2) ?
    Co1 O1 . 1.903(2) ?
    Co1 O2 . 1.910(2) ?
    Co1 N2 . 1.919(2) ?
    Co1 N1 . 1.931(2) ?
    Co1 N3 . 1.934(2) ?
    O1 C1 . 1.325(4) ?
    O2 C10 . 1.337(3) ?
    O3 C19 . 1.313(4) ?
    N1 C8 . 1.327(4) ?
    N1 C9 . 1.374(4) ?
    N2 C17 . 1.336(4) ?
    N2 C18 . 1.365(4) ?
    N3 C26 . 1.328(4) ?
    N3 C27 . 1.372(4) ?
    C1 C2 . 1.387(4) ?
    C1 C9 . 1.418(4) ?
    C2 C3 . 1.400(5) ?
    C3 C4 . 1.374(5) ?
    C4 C5 . 1.402(5) ?
    C5 C6 . 1.407(5) ?
    C5 C9 . 1.416(4) ?
    C6 C7 . 1.360(5) ?
    C7 C8 . 1.406(5) ?
    C10 C11 . 1.378(4) ?
    C10 C18 . 1.415(4) ?
    C11 C12 . 1.401(5) ?
    C12 C13 . 1.364(6) ?
    C13 C14 . 1.416(5) ?
    C14 C15 . 1.404(5) ?
    C14 C18 . 1.419(4) ?
    C15 C16 . 1.347(6) ?
    C16 C17 . 1.400(5) ?
    C19 C20 . 1.388(4) ?
    C19 C27 . 1.418(4) ?
    C20 C21 . 1.400(5) ?
    C21 C22 . 1.366(5) ?
    C22 C23 . 1.410(5) ?
    C23 C27 . 1.409(4) ?
    C23 C24 . 1.418(5) ?
    C24 C25 . 1.366(5) ?
    C25 C26 . 1.393(4) ?
    O4 C28 . 1.396(5) ?
    C28 C29 . 1.421(8) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O3 Co1 O1 . . 90.51(9) ?
    O3 Co1 O2 . . 91.99(9) ?
    O1 Co1 O2 . . 176.68(9) ?
    O3 Co1 N2 . . 87.07(10) ?
    O1 Co1 N2 . . 92.27(10) ?
    O2 Co1 N2 . . 85.68(10) ?
    O3 Co1 N1 . . 175.98(10) ?
    O1 Co1 N1 . . 85.47(9) ?
    O2 Co1 N1 . . 92.02(10) ?
    N2 Co1 N1 . . 92.87(10) ?
    O3 Co1 N3 . . 85.83(10) ?
    O1 Co1 N3 . . 92.09(10) ?
    O2 Co1 N3 . . 90.27(9) ?
    N2 Co1 N3 . . 171.70(10) ?
    N1 Co1 N3 . . 94.51(10) ?
    C1 O1 Co1 . . 111.96(18) ?
    C10 O2 Co1 . . 111.45(19) ?
    C19 O3 Co1 . . 112.13(18) ?
    C8 N1 C9 . . 119.4(3) ?
    C8 N1 Co1 . . 130.2(2) ?
    C9 N1 Co1 . . 110.45(19) ?
    C17 N2 C18 . . 120.0(3) ?
    C17 N2 Co1 . . 129.1(2) ?
    C18 N2 Co1 . . 110.7(2) ?
    C26 N3 C27 . . 119.0(3) ?
    C26 N3 Co1 . . 131.4(2) ?
    C27 N3 Co1 . . 109.67(19) ?
    O1 C1 C2 . . 125.6(3) ?
    O1 C1 C9 . . 117.2(3) y
    C2 C1 C9 . . 117.2(3) ?
    C1 C2 C3 . . 120.4(3) ?
    C4 C3 C2 . . 122.1(3) ?
    C3 C4 C5 . . 120.1(3) ?
    C4 C5 C6 . . 126.5(3) ?
    C4 C5 C9 . . 117.5(3) ?
    C6 C5 C9 . . 116.1(3) ?
    C7 C6 C5 . . 121.0(3) ?
    C6 C7 C8 . . 119.9(3) ?
    N1 C8 C7 . . 121.3(3) ?
    N1 C9 C5 . . 122.4(3) ?
    N1 C9 C1 . . 114.8(3) y
    C5 C9 C1 . . 122.7(3) ?
    O2 C10 C11 . . 125.3(3) ?
    O2 C10 C18 . . 116.7(3) y
    C11 C10 C18 . . 118.0(3) ?
    C10 C11 C12 . . 119.6(4) ?
    C13 C12 C11 . . 123.1(4) ?
    C12 C13 C14 . . 119.6(3) ?
    C15 C14 C13 . . 126.6(3) ?
    C15 C14 C18 . . 116.4(3) ?
    C13 C14 C18 . . 117.0(3) ?
    C16 C15 C14 . . 120.6(3) ?
    C15 C16 C17 . . 120.9(4) ?
    N2 C17 C16 . . 120.2(3) ?
    N2 C18 C10 . . 115.5(3) y
    N2 C18 C14 . . 121.8(3) ?
    C10 C18 C14 . . 122.7(3) ?
    O3 C19 C20 . . 124.8(3) ?
    O3 C19 C27 . . 117.4(3) y
    C20 C19 C27 . . 117.7(3) ?
    C19 C20 C21 . . 119.5(3) ?
    C22 C21 C20 . . 122.9(3) ?
    C21 C22 C23 . . 119.7(3) ?
    C27 C23 C22 . . 117.5(3) ?
    C27 C23 C24 . . 116.6(3) ?
    C22 C23 C24 . . 125.8(3) ?
    C25 C24 C23 . . 119.9(3) ?
    C24 C25 C26 . . 120.1(3) ?
    N3 C26 C25 . . 122.0(3) ?
    N3 C27 C23 . . 122.4(3) ?
    N3 C27 C19 . . 114.9(3) y
    C23 C27 C19 . . 122.6(3) ?
    O4 C28 C29 . . 113.3(6) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O3 Co1 O1 C1 . . . . -177.09(19) ?
    O2 Co1 O1 C1 . . . . -38.2(16) ?
    N2 Co1 O1 C1 . . . . -90.0(2) ?
    N1 Co1 O1 C1 . . . . 2.70(19) ?
    N3 Co1 O1 C1 . . . . 97.1(2) ?
    O3 Co1 O2 C10 . . . . 86.1(2) ?
    O1 Co1 O2 C10 . . . . -52.8(16) ?
    N2 Co1 O2 C10 . . . .  -.8(2) ?
    N1 Co1 O2 C10 . . . . -93.6(2) ?
    N3 Co1 O2 C10 . . . . 171.9(2) ?
    O1 Co1 O3 C19 . . . . -91.2(2) ?
    O2 Co1 O3 C19 . . . . 91.0(2) ?
    N2 Co1 O3 C19 . . . . 176.6(2) ?
    N1 Co1 O3 C19 . . . . -94.2(13) ?
    N3 Co1 O3 C19 . . . .  .9(2) ?
    O3 Co1 N1 C8 . . . .  -18E1(10)
                                   ?
    O1 Co1 N1 C8 . . . . 177.2(3) ?
    O2 Co1 N1 C8 . . . . -5.0(3) ?
    N2 Co1 N1 C8 . . . . -90.8(3) ?
    N3 Co1 N1 C8 . . . . 85.4(3) ?
    O3 Co1 N1 C9 . . . . 2.1(14) ?
    O1 Co1 N1 C9 . . . .  -.86(18) ?
    O2 Co1 N1 C9 . . . . 176.97(18) ?
    N2 Co1 N1 C9 . . . . 91.19(19) ?
    N3 Co1 N1 C9 . . . . -92.61(19) ?
    O3 Co1 N2 C17 . . . . 84.0(3) ?
    O1 Co1 N2 C17 . . . . -6.4(3) ?
    O2 Co1 N2 C17 . . . . 176.2(3) ?
    N1 Co1 N2 C17 . . . . -92.0(3) ?
    N3 Co1 N2 C17 . . . . 115.3(7) ?
    O3 Co1 N2 C18 . . . . -90.8(2) ?
    O1 Co1 N2 C18 . . . . 178.8(2) ?
    O2 Co1 N2 C18 . . . . 1.4(2) ?
    N1 Co1 N2 C18 . . . . 93.3(2) ?
    N3 Co1 N2 C18 . . . . -59.5(8) ?
    O3 Co1 N3 C26 . . . . -179.3(3) ?
    O1 Co1 N3 C26 . . . . -88.9(3) ?
    O2 Co1 N3 C26 . . . . 88.7(3) ?
    N2 Co1 N3 C26 . . . . 149.4(7) ?
    N1 Co1 N3 C26 . . . . -3.3(3) ?
    O3 Co1 N3 C27 . . . .  .36(19) ?
    O1 Co1 N3 C27 . . . . 90.7(2) ?
    O2 Co1 N3 C27 . . . . -91.6(2) ?
    N2 Co1 N3 C27 . . . . -30.9(8) ?
    N1 Co1 N3 C27 . . . . 176.34(19) ?
    Co1 O1 C1 C2 . . . . 176.9(2) ?
    Co1 O1 C1 C9 . . . . -4.0(3) ?
    O1 C1 C2 C3 . . . . 177.4(3) ?
    C9 C1 C2 C3 . . . . -1.7(5) ?
    C1 C2 C3 C4 . . . .  .1(5) ?
    C2 C3 C4 C5 . . . . 1.6(5) ?
    C3 C4 C5 C6 . . . . 179.3(3) ?
    C3 C4 C5 C9 . . . . -1.7(5) ?
    C4 C5 C6 C7 . . . . -179.5(3) ?
    C9 C5 C6 C7 . . . . 1.5(5) ?
    C5 C6 C7 C8 . . . . -1.0(5) ?
    C9 N1 C8 C7 . . . . -1.1(4) ?
    Co1 N1 C8 C7 . . . . -179.0(2) ?
    C6 C7 C8 N1 . . . .  .7(5) ?
    C8 N1 C9 C5 . . . . 1.7(4) ?
    Co1 N1 C9 C5 . . . . 180.0(2) ?
    C8 N1 C9 C1 . . . . -179.3(3) ?
    Co1 N1 C9 C1 . . . . -1.0(3) ?
    C4 C5 C9 N1 . . . . 179.0(3) ?
    C6 C5 C9 N1 . . . . -1.8(4) ?
    C4 C5 C9 C1 . . . .  .1(4) ?
    C6 C5 C9 C1 . . . . 179.2(3) ?
    O1 C1 C9 N1 . . . . 3.4(4) ?
    C2 C1 C9 N1 . . . . -177.4(3) ?
    O1 C1 C9 C5 . . . . -177.6(3) ?
    C2 C1 C9 C5 . . . . 1.6(4) ?
    Co1 O2 C10 C11 . . . . 179.5(3) ?
    Co1 O2 C10 C18 . . . .  .1(3) ?
    O2 C10 C11 C12 . . . . -180.0(3) ?
    C18 C10 C11 C12 . . . .  -.6(5) ?
    C10 C11 C12 C13 . . . .  -.9(6) ?
    C11 C12 C13 C14 . . . .  .9(6) ?
    C12 C13 C14 C15 . . . . -179.6(4) ?
    C12 C13 C14 C18 . . . .  .7(5) ?
    C13 C14 C15 C16 . . . . 179.8(4) ?
    C18 C14 C15 C16 . . . .  -.5(5) ?
    C14 C15 C16 C17 . . . . 1.6(6) ?
    C18 N2 C17 C16 . . . . -1.3(5) ?
    Co1 N2 C17 C16 . . . . -175.6(3) ?
    C15 C16 C17 N2 . . . .  -.7(6) ?
    C17 N2 C18 C10 . . . . -177.1(3) ?
    Co1 N2 C18 C10 . . . . -1.8(3) ?
    C17 N2 C18 C14 . . . . 2.4(5) ?
    Co1 N2 C18 C14 . . . . 177.8(2) ?
    O2 C10 C18 N2 . . . . 1.2(4) ?
    C11 C10 C18 N2 . . . . -178.3(3) ?
    O2 C10 C18 C14 . . . . -178.4(3) ?
    C11 C10 C18 C14 . . . . 2.2(5) ?
    C15 C14 C18 N2 . . . . -1.5(5) ?
    C13 C14 C18 N2 . . . . 178.3(3) ?
    C15 C14 C18 C10 . . . . 178.0(3) ?
    C13 C14 C18 C10 . . . . -2.2(5) ?
    Co1 O3 C19 C20 . . . . 178.4(3) ?
    Co1 O3 C19 C27 . . . . -2.0(3) ?
    O3 C19 C20 C21 . . . . 178.5(3) ?
    C27 C19 C20 C21 . . . . -1.2(5) ?
    C19 C20 C21 C22 . . . .  .1(5) ?
    C20 C21 C22 C23 . . . . 1.1(6) ?
    C21 C22 C23 C27 . . . . -1.1(5) ?
    C21 C22 C23 C24 . . . . 177.1(3) ?
    C27 C23 C24 C25 . . . .  -.2(5) ?
    C22 C23 C24 C25 . . . . -178.5(3) ?
    C23 C24 C25 C26 . . . .  .0(5) ?
    C27 N3 C26 C25 . . . .  .7(5) ?
    Co1 N3 C26 C25 . . . . -179.7(2) ?
    C24 C25 C26 N3 . . . .  -.2(5) ?
    C26 N3 C27 C23 . . . .  -.9(4) ?
    Co1 N3 C27 C23 . . . . 179.4(2) ?
    C26 N3 C27 C19 . . . . 178.2(3) ?
    Co1 N3 C27 C19 . . . . -1.5(3) ?
    C22 C23 C27 N3 . . . . 179.1(3) ?
    C24 C23 C27 N3 . . . .  .6(4) ?
    C22 C23 C27 C19 . . . .  .0(5) ?
    C24 C23 C27 C19 . . . . -178.4(3) ?
    O3 C19 C27 N3 . . . . 2.3(4) ?
    C20 C19 C27 N3 . . . . -178.0(3) ?
    O3 C19 C27 C23 . . . . -178.5(3) ?
    C20 C19 C27 C23 . . . . 1.1(5) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    O4 H4B O2 . . 1_555  .82 2.20 2.777(4) 128 yes
    C4 H4A O1 . . 2_655  .93 2.54 3.380(4) 150 yes
    C24 H24A O1 . . 3_665  .93 2.59 3.390(4) 145 yes
    C15 H15A Cg1 . . 3_666  .93 2.58 3.496(4) 168 yes
