

















 
#------------------ SECTION 1. GLOBAL INFORMATION ---------------------------#
 
data_global
 
#------------------ AUDIT DETAILS -------------------------------------------#
 
_audit_creation_date            2004-03-23
_audit_creation_method          'PrintCIF'
_audit_conform_dict_name        cif_core.dic
_audit_conform_dict_version     2.2
_audit_conform_dict_location    ftp://ftp.iucr.org/pub/cif_core.dic
_audit_update_record            ?
 
#------------------ SUBMISSION DETAILS --------------------------------------#
 
# Name and address of author for correspondence
 
_publ_contact_author_name      'Robert J. Lancashire'
_publ_contact_author_address
'Department of Chemistry, UWI, Mona Campus, Kingston 7, JAMAICA, W.I.'

_publ_contact_author_email      Robert.Lancashire@uwimona.edu.jm
_publ_contact_author_fax         '876 9771835'
_publ_contact_author_phone    '876 9271910'
 
_publ_requested_journal          'Acta Crystallographica Section C'
_publ_requested_coeditor_name    ?
_publ_contact_letter            # Include date of submission
;
Date of submission ?
 
Please consider this CIF submission for publication as a
Regular Structural Paper in Acta Crystallographica C.
;
_publ_requested_category        ?
 
#------------------ PROCESSING SUMMARY (JOURNAL OFFICE ONLY) ----------------#
 
_journal_date_recd_electronic    ?
_journal_date_to_coeditor        ?
_journal_date_from_coeditor      ?
_journal_date_accepted           ?
_journal_date_printers_first     ?
_journal_date_printers_final     ?
_journal_date_proofs_out         ?
_journal_date_proofs_in          ?
_journal_coeditor_name           ?
_journal_coeditor_code           ?
_journal_coeditor_notes          ?
_journal_techeditor_code         ?
_journal_techeditor_notes        ?
_journal_coden_ASTM              ?
_journal_name_full               ?
_journal_year                    ?
_journal_volume                  ?
_journal_issue                   ?
_journal_page_first              ?
_journal_page_last               ?
_journal_suppl_publ_number       ?
_journal_suppl_publ_pages        ?
 
#------------------ TITLE AND AUTHOR LIST------------------------------------#
 
_publ_section_title 
'trans-bis(glycinato-N,O)copper(II) 4-bromophenol solvate, trans-[Cu(gly)2].4-BrPhOH'

 _publ_section_title_footnote
;
?
;
 
loop_
_publ_author_name
_publ_author_address
'Mohammed Bakir'
'Department of Chemistry, UWI, Mona Campus, Kingston 7, Jamaica W.I.'

'Suzanne A. Clarke'
'Department of Chemistry, UWI, Mona Campus, Kingston 7, Jamaica W.I.'

'Ishmael Hassan'
'Department of Chemistry, UWI, Mona Campus, Kingston 7, Jamaica W.I.'

'Robert J. Lancashire^#^'
'Department of Chemistry, UWI, Mona Campus, Kingston 7, Jamaica W.I.'

'Marvadeen Singh-Wilmot'
'Department of Chemistry, UWI, Mona Campus, Kingston 7, Jamaica W.I.'
#------------------ TEXT ----------------------------------------------------#
 
_publ_section_abstract
;
trans-bis(glycinato--N,O)copper(II) 4-bromophenol solvate, 
trans-[Cu(gly)₂].4--BrPhOH (1), crystallized in the 
noncentrosymmetric orthorhombic space group Pca2(1) when a quantity of (1) 
was allowed to stand in water for several days. Structural analysis reveals 
well separated trans-bis(glycinato--N,O) copper(II) and 4-bromophenol. 
The coordination about copper is square planar with the glycinato units in 
N,O-bidentate binding modes. The packing of molecules shows infinite stacks 
of chains of (1) interlocked via a network of non-covalent bonds with copper 
in six coordination mode and 4--BrPhOH bridging adjacent stacks.
;
 
_publ_section_comment
;
Copper complexes of glycine have been extensively studied for their 
physico-chemical properties (Beattie et al., 1976, Percy, 1976, Gillard et 
al., 1980, Goodman et al., 1981, Szabo-Planka, 1985, Efstathiou et al., 
2003). In particular, the unusual cis- trans-isomer conversion 
in the solid state of bis(glycinato--N,O)copper(II) (Delf, et al., 1979) and 
its biomimetic behavior in water (Davies et al., 2003) Although structural 
studies on bis(glycinato--N,O)copper(II) compounds 
cis-[Cu(gly)₂].H₂O), trans-[Cu(gly)₂].2AgNO₃, 
trans-Cu(gly)₂].Mg(H₂O)₆]. H₂O, a hexanuclear copper(II) 
complex Na[NaCu₆(gly)₈(H₂O)₂](ClO₄)₆.2 H₂O containing 
cis- coordinated glycine and mono-glycinato copper(II) compounds 
[Cu(gly)(OH₂)₄]⁺ and [Cu(gly)(NO₃)(OH₂)] were reported (Freeman et 
al., 1964, Davies et al., 2003, 1992, Hu et al., 2001), to our knowledge the 
structure of (1) is not known. As early as the 1940's, it was realised that 
addition of phenols caused the precipitation of dark blue salts Cu(gly)₂ 
2X, (Wieland et al., 1949) but the nature of these products was not 
determined and attempts to crystallise salts of this type (where X is phenol 
or a substituted phenol) suitable for X-ray analysis were futile. With picric 
acid, crystals of Cu(gly)₂.2picric acid.6H₂O were isolated in which the 
glycine was found to bind to copper in a unidentate coordination mode (Davies 
et al., 1995). Our continued interest in the interactions between α-amino 
acids and metal ions led to this report in which we describe the first 
structure of this type. 

A displacement ellipsoid plot of (1) is shown in Figure 1 and shows well 
separated trans-[Cu(gly)₂] and 4-bromophenol moieties. The 
coordinated sites of copper are occupied by two nitrogen and two O atoms of 
coordinated glycinato ligands in a square planar geometry. The O,N-bidentate 
glycinato ligands form two planar fused five-membered metallocyclic rings 
(Cu---N---C---C---O) with coordinated O's and N's in trans- geometry. 
The bond distances and angles of the coordinated atoms are normal (see Table 
1) and similar to those reported for a variety of Cu(II) glycinato compounds. 
For example, an O---Cu---N bite angle of 84.90º and d(Cu ---O) and d(Cu 
--- N) bond distances of 1.94 and 1.98 Å were reported for 
[Cu(gly)(NO₃)(H₂O)] (Davies et al., 1992). In the case of 
cis-[Cu(gly)₂].H₂O an average O---Cu---N bite angle of 85.20º 
(2) and Cu---O and Cu---N bond distances of 1.94 (2) and 2.00 (2) Å were 
reported (Freeman, et al., 1964). 

The molecular packing shows infinite stacks of chains of 
trans-[Cu(gly)₂].4-bromophenol units interlocked via a network of 
non-covalent bonds (see Table 2 and Figure 2). In the stacks, the 
coordination geometry around the coppers is six showing a Jahn-Teller 
distorted octahedral with the equatorial sites occupied by the covalent 
binding of N,O-bidentate glycinato units and the axial sites occupied by 
uncoordinated O atoms of the carboxylates of adjacent 
trans-[Cu(gly)₂] chains (see Figure 3). The axial non-covalent 
Cu---O bonds are not equivalent as apparent from their Cu---O bond distances 
of 2.48 and 2.83 Å but are of the same order as those observed in 
cis-[Cu(gly)₂(H₂O)] and other related compounds. For example, in 
cis- [Cu(gly)₂(H₂O)], axial d(Cu---O) of 2.40 and 2.74 Å were 
reported (Freeman, et al., 1964).The solvated 4-bromophenol units interlock 
adjacent strands of trans-[Cu(gly)₂] units via bifurcated 
non-covalent interactions as shown in Figure 4. The bond distances and angles 
of the non-covalent interactions are normal and similar to those reported for 
a variety of compounds containing such bonds. For example, in 
cis-[Cu(L-isoLeucine)₂], the following hydrogen bond parameters were 
reported: d(HA), d(DA) and <(DHA) of O---H---O and N---H---O 2.22 (3), 
2.87 (2), 156 (5) and 2.24 (2), 3.00 (2), 149 (4) (Weeks, et al. 1969). 

Due to the bioactivity of α-amino acids and their metal compounds, and 
current interest in developing technologies based on biomolecules, work is in 
progress in our laboratory to prepare single crystals of a variety of metal 
compounds of biomolecules that include α-amino acids
;
 
_publ_section_exptl_prep
;
trans-[Cu(gly)₂].4-bromophenol was synthesized from the reaction of 
a mixture of [CuSO₄.5H₂O], glycine and 4-bromophenol in distilled water 
in a procedure similar to those reported in the literature for the synthesis 
of a variety of copper-bis-glycinato compounds of the type [Cu(gly)₂].2X 
where X = solvate or salts of group I and II metal compounds (Wieland and 
Wirth, 1949, Davies, et al., 2003). Blue crystals, suitable for X-ray 
analysis, were obtained when a quantity of (1) was allowed to stand in 
distilled water for several days. 
;
 
_publ_section_exptl_refinement
;
Experimental refinement missing 
;
 
# Insert blank lines between references
 
_publ_section_references
;
Beattie, J. K. Fensom, D. J. & Freeman, H. C. (1976), J. Amer. Chem. Soc., 
98, 500-507. 

Bruker-SHELXTL (1997). Software Version 5.1. Brucker AXS, Inc., Madison, 
Wisconsin, USA. 

Burla M.C., Camalli M., Carrozzini B., Cascarano G.L., Giacovazzo C., 
Polidori G., Spagna R.. Sir2002: a new Direct Methods program for automatic 
solution and refinement of crystal structures J. Appl. Cryst. (2003). In 
preparation 

Davies, H. O., Park, J.-H. & Gillard, R. D. (2003). Inorg. Chim. Acta 
356, 69--84. 

Davies, H. O., Gillard, R. D., Hursthouse, M. B., Mazid, M. A. & Williams, P. 
A. (1992). J. Chem. Soc. Chem. Commun. pp. 226--228. 

Delf, B. W., Gillard, R. D. & O'Brien, P. (1979). J. Chem. Soc., Dalton 
Trans. pp. 1301--1305. 

Efstathiou, V. & Woodruff, D. P. (2003). Surface Science 531, 
304--318. 

Farrugia, L.J. (1999) WinGX. A Windows Program for Crystal Structure 
Analysis. Journal of Applied Crystallography, 32, 837--838. 

Farrugia, L.J. (1997) ORTEP3 for Windows---a version of ORTEP-III with a 
Graphical User Interface (GUI). Journal of Applied Crystallography, 
30, 565. 

Freeman, H. C., Nitta, M. R. & Tomita, K. (1964). Acta Cryst. 17, 
1463--1470. 

Gillard, R. D., Lancashire, R. J. & O'Brien, P. (1980). Transition Met. Chem. 
5, 340--345. 

Goodman, B.A. McPhail, D. B. & Powell H. K. J. (1981) J. Chem. Soc. Dalton 
Trans., pp. 822-827 

Hu S., Du W., Dai J., Wu L., Cui C., Fu Z., Wu X. (2001), J. Chem. Soc., 
Dalton Trans., pp 2963-2964. 

Percy, G. C. (1976), Spectrochim. Acta, 32A, 1287-1290. 

Sheldrick, G. M. (1990). Acta Cryst. A46, 467--473. 

Sheldrick, G. M. (1997). SHELX97 and SHELXL97. University of Gottengen, 
Germany. Weeks, C. M., Cooper, A. & Norton, D. A. (1969). Acta Cryst. 
B25, 443--450. 

Szabo-Planka T (1985), Acta Chim. Hung., 120, 143-151 

Wieland, T. & Wirth L. (1949). Chem. Ber. 82, 468--473.
;
_publ_section_figure_captions
;
Figure 1. A drawing of the molecular structure of (1). The thermal ellipsoids 
are drawn at the 30% probability level. 

Figure 2. A packing diagram for (1). Hydrogen bonds are shown by dashed 
lines. 

Figure 3. A view showing the coordination of Cu in the stacks. 

Figure 4. A view showing the non-covalent binding of 4-bromophenol to 
adjacent strands of trans- [Cu(gly)₂] units.
;
_publ_section_table_legends
;
Table 1. Fractional atomic coordinates and equivalent
         isotropic displacement parameters (Å²)
 
Table 2. Selected geometric parameters (Å ,° )
;
 
#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------#
 
data_glycubr
 
_audit_creation_date            2004-03-07T16:20:45-00:00
_audit_creation_method         ?
 
#------------------ CHEMICAL INFORMATION ------------------------------------#
 
_chemical_formula_moiety                'C10 H13 Br1 Cu1 N2 O5'
_chemical_formula_sum
                                       'C40 H52 Br4 Cu4 N8 O20'
_chemical_formula_weight                512.9
_chemical_absolute_configuration        unk
 
#------------------ UNIT CELL INFORMATION -----------------------------------#
 
_symmetry_cell_setting                  orthorhombic
_symmetry_space_group_name_H-M          'P c a 21'
_symmetry_Int_Tables_number 29
loop_
    _symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
 
_cell_length_a                          9.4420(10)
_cell_length_b                          5.0630(10)
_cell_length_c                          27.926(4)
_cell_angle_alpha                       90
_cell_angle_beta                        90
_cell_angle_gamma                       90
_cell_volume                            1335.0(4)
_cell_formula_units_Z                   4
_cell_measurement_temperature           293(2)
_cell_measurement_reflns_used           0
_cell_measurement_theta_min             0
_cell_measurement_theta_max             0
 
#------------------ CRYSTAL INFORMATION -------------------------------------#
 
_exptl_crystal_description              prism
_exptl_crystal_colour                   Blue
_exptl_crystal_size_max                 0.26
_exptl_crystal_size_mid                 0.18
_exptl_crystal_size_min                 0.06
_exptl_crystal_density_diffrn           1.914
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    764
_exptl_absorpt_coefficient_mu           4.646
_exptl_absorpt_correction_type          none
 
#------------------ DATA COLLECTION INFORMATION -----------------------------#
 
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_probe                 x-ray
_diffrn_reflns_number                   1691
_diffrn_reflns_av_R_equivalents         0.0446
_diffrn_reflns_limit_h_min              -1
_diffrn_reflns_limit_h_max              11
_diffrn_reflns_limit_k_min              -1
_diffrn_reflns_limit_k_max              6
_diffrn_reflns_limit_l_min              -1
_diffrn_reflns_limit_l_max              33
_diffrn_reflns_theta_min                2.92
_diffrn_reflns_theta_max                24.99
_diffrn_reflns_theta_full               24.99
_diffrn_measured_fraction_theta_max     0.971
_diffrn_measured_fraction_theta_full    0.971
_diffrn_standards_interval_count 97
_diffrn_standards_number 3
_diffrn_standards_decay_%  0
_diffrn_measurement_device_type 'Bruker P4' 
_diffrn_measurement_method '2θ/ω'
 
#------------------ COMPUTER PROGRAMS USED ----------------------------------#
 
_computing_structure_solution           'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement         'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics           'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
 
#------------------ REFINEMENT INFORMATION ----------------------------------#
 
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0578P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment           mixed
_refine_ls_extinction_method            SHELXL
_refine_ls_extinction_expression
                                    Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef              0.0012(9)
_refine_ls_number_reflns                1214
_refine_ls_number_parameters            174
_refine_ls_number_restraints            1
_refine_ls_R_factor_gt                  0.0423
_refine_ls_wR_factor_ref                0.1038
_refine_ls_goodness_of_fit_ref          1.032
_refine_ls_restrained_S_all             1.032
_refine_ls_shift/su_max                 0
_refine_ls_abs_structure_details  
'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack          0.07(3)
_refine_diff_density_max                0.469
_refine_diff_density_min                -0.394
_refine_diff_density_rms    		    0.103 

_reflns_number_total                    1214
_reflns_number_gt                       983
_reflns_threshold_expression            >2sigma(I)


 
#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#
 
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
loop_
    _atom_site_label
    _atom_site_type_symbol
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_occupancy
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_disorder_group
    _atom_site_disorder_assembly
Cu Cu 0.36333(11) 0.2586(2) 0.21775(5) 0.0313(3) Uani 1 d . . .
O1 O 0.5170(6) 0.0230(12) 0.2382(2) 0.0327(16) Uani 1 d . . .
C3 C 0.1190(9) 0.3839(19) 0.1698(4) 0.030(2) Uani 1 d . . .
O2 O 0.1987(6) 0.4766(12) 0.2029(2) 0.0315(16) Uani 1 d . . .
C1 C 0.5892(11) 0.0951(17) 0.2738(4) 0.030(2) Uani 1 d . . .
C2 C 0.5388(11) 0.3426(18) 0.2996(4) 0.037(2) Uani 1 d . . .
H2B H 0.4977 0.2941 0.3302 0.044 Uiso 1 calc R . .
H2A H 0.6189 0.4577 0.3057 0.044 Uiso 1 calc R . .
N1 N 0.2867(9) 0.0151(14) 0.1683(3) 0.033(2) Uani 1 d . . .
H1B H 0.3562 -0.0325 0.148 0.04 Uiso 1 calc R . .
H1A H 0.2529 -0.1318 0.1824 0.04 Uiso 1 calc R . .
C4 C 0.1733(11) 0.147(2) 0.1419(3) 0.032(2) Uani 1 d . . .
H4A H 0.0963 0.024 0.1364 0.038 Uiso 1 calc R . .
H4B H 0.2087 0.2049 0.111 0.038 Uiso 1 calc R . .
O3 O 0.6931(8) -0.0238(14) 0.2894(3) 0.0442(19) Uani 1 d . . .
O4 O 0.0023(8) 0.4821(14) 0.1585(3) 0.0411(18) Uani 1 d . . .
N2 N 0.4325(8) 0.4845(15) 0.2707(3) 0.0306(19) Uani 1 d . . .
H2C H 0.4714 0.6324 0.2586 0.037 Uiso 1 calc R . .
H2D H 0.3592 0.5318 0.2895 0.037 Uiso 1 calc R . .
Br Br 0.61815(14) 0.3466(3) 0.55637(4) 0.0669(5) Uani 1 d . . .
O5 O 0.8520(9) 0.1758(17) 0.3582(3) 0.051(2) Uani 1 d . . .
H5B H 0.8087 0.0591 0.3441 0.076 Uiso 1 calc R . .
C5 C 0.6293(13) 0.103(3) 0.4647(5) 0.060(3) Uani 1 d . . .
H5 H 0.5531 0.004 0.4759 0.072 Uiso 1 calc R . .
C6 C 0.6809(13) 0.063(2) 0.4187(4) 0.049(3) Uani 1 d . . .
H6 H 0.639 -0.0615 0.3988 0.058 Uiso 1 calc R . .
C7 C 0.7951(12) 0.210(2) 0.4026(4) 0.044(3) Uani 1 d . . .
C9 C 0.8026(15) 0.431(3) 0.4784(4) 0.058(3) Uani 1 d . . .
H9 H 0.846 0.5527 0.4987 0.07 Uiso 1 calc R . .
C10 C 0.6913(12) 0.290(2) 0.4937(4) 0.042(3) Uani 1 d . . .
C8 C 0.8521(12) 0.395(3) 0.4322(5) 0.056(3) Uani 1 d . . .
H8 H 0.926 0.5004 0.4211 0.067 Uiso 1 calc R . .
 
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_23
    _atom_site_aniso_U_13
    _atom_site_aniso_U_12
Cu 0.0278(5) 0.0226(5) 0.0435(7) -0.0058(5) -0.0087(7) 0.0030(5)
O1 0.031(3) 0.022(3) 0.045(4) -0.004(3) -0.011(3) 0.002(3)
C3 0.018(4) 0.035(5) 0.038(5) 0.003(5) 0.002(5) -0.010(5)
O2 0.025(3) 0.025(3) 0.045(4) -0.005(3) -0.001(3) 0.007(3)
C1 0.037(5) 0.026(5) 0.028(5) 0.004(4) 0.008(5) -0.003(5)
C2 0.036(5) 0.031(5) 0.044(6) -0.010(5) 0.005(5) 0.000(5)
N1 0.034(4) 0.024(4) 0.042(5) 0.000(4) 0.013(4) 0.004(4)
C4 0.037(5) 0.029(5) 0.029(5) -0.004(4) -0.003(4) 0.010(4)
O3 0.044(4) 0.035(4) 0.054(5) -0.004(4) -0.016(4) 0.015(4)
O4 0.040(4) 0.044(5) 0.039(4) -0.003(3) -0.007(4) 0.015(3)
N2 0.029(4) 0.027(4) 0.036(4) -0.008(3) 0.005(4) -0.003(4)
Br 0.0679(8) 0.0926(10) 0.0401(6) -0.0025(9) 0.0026(8) 0.0030(8)
O5 0.063(5) 0.055(5) 0.033(4) -0.007(4) 0.007(4) -0.022(4)
C5 0.049(7) 0.075(9) 0.056(8) -0.001(7) 0.012(7) -0.013(7)
C6 0.060(7) 0.042(6) 0.044(7) -0.004(5) 0.000(6) -0.014(6)
C7 0.036(6) 0.045(7) 0.052(7) 0.011(5) -0.007(5) 0.003(5)
C9 0.066(8) 0.063(8) 0.046(7) -0.012(6) -0.006(7) -0.020(7)
C10 0.043(6) 0.055(7) 0.027(5) -0.004(5) -0.004(5) 0.004(6)
C8 0.053(7) 0.066(9) 0.048(7) -0.009(7) 0.001(6) -0.020(7)
 
 
#------------------ MOLECULAR GEOMETRY --------------------------------------#
 
_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_distance
    _geom_bond_site_symmetry_2
    _geom_bond_publ_flag
Cu O2 1.952(6) . ?
Cu O1 1.963(6) . ?
Cu N2 1.981(8) . ?
Cu N1 1.987(8) . ?
O1 C1 1.260(12) . ?
C3 O4 1.249(12) . ?
C3 O2 1.280(12) . ?
C3 C4 1.520(14) . ?
C1 O3 1.231(12) . ?
C1 C2 1.522(13) . ?
C2 N2 1.475(13) . ?
N1 C4 1.462(12) . ?
Br C10 1.904(11) . ?
O5 C7 1.362(14) . ?
C5 C10 1.374(17) . ?
C5 C6 1.390(18) . ?
C6 C7 1.384(16) . ?
C7 C8 1.361(16) . ?
C9 C10 1.343(18) . ?
C9 C8 1.386(18) . ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
O2 Cu O1 173.9(3) . . ?
O2 Cu N2 95.5(3) . . ?
O1 Cu N2 83.7(3) . . ?
O2 Cu N1 85.0(3) . . ?
O1 Cu N1 95.4(3) . . ?
N2 Cu N1 175.7(4) . . ?
C1 O1 Cu 117.0(6) . . ?
O4 C3 O2 123.8(9) . . ?
O4 C3 C4 118.8(9) . . ?
O2 C3 C4 117.5(8) . . ?
C3 O2 Cu 114.5(6) . . ?
O3 C1 O1 124.7(9) . . ?
O3 C1 C2 119.0(9) . . ?
O1 C1 C2 116.3(9) . . ?
N2 C2 C1 110.7(8) . . ?
C4 N1 Cu 109.5(6) . . ?
N1 C4 C3 110.4(8) . . ?
C2 N2 Cu 110.6(6) . . ?
C10 C5 C6 119.7(11) . . ?
C7 C6 C5 119.7(11) . . ?
C8 C7 O5 118.9(10) . . ?
C8 C7 C6 118.8(12) . . ?
O5 C7 C6 122.3(11) . . ?
C10 C9 C8 119.3(11) . . ?
C9 C10 C5 120.9(11) . . ?
C9 C10 Br 119.7(9) . . ?
C5 C10 Br 119.4(9) . . ?
C7 C8 C9 121.5(12) . . ?
 
_exptl_absorpt_correction_T_min 0.191

_exptl_absorpt_correction_T_max 0.308
    
_computing_data_collection 'Bruker XSCANS'
 
_computing_cell_refinement 'Bruker XSCANS, SIR2002 (Burla et al., 2003) '
 
_computing_data_reduction 'Bruker XSCANS'
 

