#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/42/2204263.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2204263
loop_
_publ_author_name
'Vencato, Ivo'
'Lariucci, Carlito'
'Ferreira, Katiuscia D.'
'Santana, Ricardo C.'
'Carvalho, Jesiel F.'
_publ_section_title
;
 Redetermination of bis(<small>L</small>-asparaginato)copper(II)
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1428
_journal_page_last               m1430
_journal_paper_doi               10.1107/S1600536804022202
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          '[Cu (C4 H7 N2 O3 )2]'
_chemical_formula_moiety         'C8 H14 Cu N4 O6'
_chemical_formula_structural
;
 [Cu(OOC.CHNH~2~.CH~2~.CONH~2~)~2~]~n~
;
_chemical_formula_sum            'C8 H14 Cu N4 O6'
_chemical_formula_weight         325.77
_chemical_name_common
;
catena-(bis(υ₂-L-asparaginato-N,O,O')copper(II)
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 96.21(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.036(2)
_cell_length_b                   18.915(2)
_cell_length_c                   6.1520(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      58.3
_cell_measurement_theta_min      14.4
_cell_volume                     582.6(3)
_computing_cell_refinement       CAD-4/PC
_computing_data_collection       'CAD-4/PC (Enraf-Nonius, 1993)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
;
 Ortep-3 for Windows (Farrugia, 1997)
;
_computing_publication_material
;
WinGX publication routines (Farrugia, 1999)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.001
_diffrn_measurement_device_type  'Nonius CAD-4 diffractometer'
_diffrn_measurement_method       ω--2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.020
_diffrn_reflns_av_sigmaI/netI    0.018
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            2230
_diffrn_reflns_theta_full        73.9
_diffrn_reflns_theta_max         73.9
_diffrn_reflns_theta_min         4.68
_diffrn_standards_decay_%        <1.0
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    2.99
_exptl_absorpt_correction_T_max  0.796
_exptl_absorpt_correction_T_min  0.572
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'North, Phillips & Mathews (1968)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.857
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             334
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.44
_refine_diff_density_min         -0.58
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_coef       0.058(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.23
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         1228
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.22
_refine_ls_R_factor_all          0.034
_refine_ls_R_factor_gt           0.034
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0527P)²+0.3521P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.092
_refine_ls_wR_factor_ref         0.092
_reflns_number_gt                1226
_reflns_number_total             1228
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6505.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2204263
_cod_database_fobs_code          2204263
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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_type_symbol
Cu 0.78210(12) 0.62217(4) 0.22094(10) 0.0328(3) Uani d . 1 Cu
O11 0.5925(6) 0.71513(17) 0.2267(5) 0.0289(6) Uani d . 1 O
O12 0.5780(9) 0.8239(2) 0.0992(7) 0.0485(10) Uani d . 1 O
O13 1.1285(9) 0.6765(2) -0.4130(6) 0.0451(9) Uani d . 1 O
N11 1.0333(8) 0.6784(2) 0.0508(6) 0.0275(7) Uani d D 1 N
H1N 1.176(10) 0.680(3) 0.158(8) 0.033 Uiso d D 1 H
H2N 1.081(11) 0.659(3) -0.056(8) 0.033 Uiso d D 1 H
N12 1.1722(9) 0.7923(3) -0.4892(7) 0.0363(9) Uani d D 1 N
H3N 1.088(13) 0.830(3) -0.512(12) 0.044 Uiso d D 1 H
H4N 1.276(12) 0.787(4) -0.583(9) 0.044 Uiso d D 1 H
C11 0.6800(9) 0.7654(2) 0.1141(7) 0.0271(9) Uani d . 1 C
C12 0.9237(8) 0.7494(2) -0.0097(7) 0.0239(8) Uani d . 1 C
H2A 1.0620 0.7848 0.0319 0.029 Uiso calc R 1 H
C13 0.8352(9) 0.7567(3) -0.2569(7) 0.0290(9) Uani d . 1 C
H3A 0.6861 0.7251 -0.2971 0.035 Uiso calc R 1 H
H3B 0.7748 0.8046 -0.2881 0.035 Uiso calc R 1 H
C14 1.0608(9) 0.7393(3) -0.3938(7) 0.0279(9) Uani d . 1 C
O21 1.0112(7) 0.53481(19) 0.2708(6) 0.0355(8) Uani d . 1 O
O22 1.0387(9) 0.4344(2) 0.4533(7) 0.0442(9) Uani d . 1 O
O23 0.5274(8) 0.57414(19) 0.9404(5) 0.0359(7) Uani d . 1 O
N21 0.5907(8) 0.5780(2) 0.4653(6) 0.0281(8) Uani d D 1 N
H5N 0.564(11) 0.611(3) 0.565(8) 0.034 Uiso d D 1 H
H6N 0.452(11) 0.555(3) 0.391(9) 0.034 Uiso d D 1 H
N22 0.3578(11) 0.4669(3) 1.0040(9) 0.0463(11) Uani d D 1 N
H7N 0.367(15) 0.422(2) 0.996(13) 0.056 Uiso d D 1 H
H8N 0.274(14) 0.479(4) 1.112(9) 0.056 Uiso d D 1 H
C21 0.9529(9) 0.4945(2) 0.4243(7) 0.0278(9) Uani d . 1 C
C22 0.7815(8) 0.5280(2) 0.5880(7) 0.0258(8) Uani d . 1 C
H2B 0.9018 0.5566 0.6883 0.031 Uiso calc R 1 H
C23 0.6522(9) 0.4753(2) 0.7254(7) 0.0303(9) Uani d . 1 C
H3C 0.7882 0.4437 0.7939 0.036 Uiso calc R 1 H
H3D 0.5263 0.4471 0.6315 0.036 Uiso calc R 1 H
C24 0.5075(9) 0.5095(2) 0.9008(7) 0.0286(9) Uani d . 1 C
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O11 Cu O21 . . 168.86(15) yes
O11 Cu N11 . . 82.75(14) yes
O21 Cu N11 . . 97.44(15) yes
O11 Cu N21 . . 94.70(14) yes
O21 Cu N21 . . 82.04(14) yes
N11 Cu N21 . . 164.02(16) yes
O11 Cu O23 . 1_554 97.81(14) yes
O21 Cu O23 . 1_554 93.18(15) yes
N11 Cu O23 . 1_554 98.80(14) yes
N21 Cu O23 . 1_554 97.18(15) yes
O23 Cu O13 1_554 1_556 176.61(13) yes
O11 Cu O13 . 1_556 85.56(12) yes
O21 Cu O13 . 1_556 83.45(13) yes
N11 Cu O13 . 1_556 81.82(14) yes
N21 Cu O13 . 1_556 82.26(14) yes
C11 O11 Cu . . 116.7(3) yes
C12 N11 Cu . . 111.6(3) yes
C12 N11 H1N . . 113(4) ?
Cu N11 H1N . . 97(4) ?
C12 N11 H2N . . 110(4) ?
Cu N11 H2N . . 116(4) ?
H1N N11 H2N . . 109(6) ?
C14 N12 H3N . . 119(5) ?
C14 N12 H4N . . 125(5) ?
H3N N12 H4N . . 109(7) ?
O12 C11 O11 . . 123.1(4) yes
O12 C11 C12 . . 119.5(4) yes
O11 C11 C12 . . 117.4(4) yes
N11 C12 C11 . . 110.4(3) yes
N11 C12 C13 . . 112.8(3) yes
C11 C12 C13 . . 108.0(3) yes
N11 C12 H2A . . 108.5 ?
C11 C12 H2A . . 108.5 ?
C13 C12 H2A . . 108.5 ?
C14 C13 C12 . . 111.9(4) yes
C14 C13 H3A . . 109.2 ?
C12 C13 H3A . . 109.2 ?
C14 C13 H3B . . 109.2 ?
C12 C13 H3B . . 109.2 ?
H3A C13 H3B . . 107.9 ?
O13 C14 N12 . . 123.3(5) yes
O13 C14 C13 . . 119.2(4) yes
N12 C14 C13 . . 117.5(4) yes
C21 O21 Cu . . 115.4(3) yes
C24 O23 Cu . 1_556 125.3(3) yes
C22 N21 Cu . . 107.5(3) yes
C22 N21 H5N . . 103(4) ?
Cu N21 H5N . . 109(4) ?
C22 N21 H6N . . 112(4) ?
Cu N21 H6N . . 103(4) ?
H5N N21 H6N . . 121(6) ?
C24 N22 H7N . . 123(5) ?
C24 N22 H8N . . 124(6) ?
H7N N22 H8N . . 111(8) ?
O22 C21 O21 . . 124.0(4) yes
O22 C21 C22 . . 120.3(4) yes
O21 C21 C22 . . 115.5(4) yes
N21 C22 C23 . . 114.3(4) yes
N21 C22 C21 . . 107.9(3) yes
C23 C22 C21 . . 113.9(4) yes
N21 C22 H2B . . 106.8 ?
C23 C22 H2B . . 106.8 ?
C21 C22 H2B . . 106.8 ?
C22 C23 C24 . . 113.0(4) yes
C22 C23 H3C . . 109.0 ?
C24 C23 H3C . . 109.0 ?
C22 C23 H3D . . 109.0 ?
C24 C23 H3D . . 109.0 ?
H3C C23 H3D . . 107.8 ?
O23 C24 N22 . . 123.0(4) yes
O23 C24 C23 . . 121.6(4) yes
N22 C24 C23 . . 115.4(4) yes
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
Cu O11 . 2.003(3) yes
Cu O21 . 2.020(3) yes
Cu N11 . 2.029(4) yes
Cu N21 . 2.049(4) yes
Cu O13 1_556 2.885(4) yes
Cu O23 1_554 2.229(4) yes
O11 C11 . 1.282(6) yes
O12 C11 . 1.219(6) yes
O13 C14 . 1.244(6) yes
N11 C12 . 1.483(5) yes
N11 H1N . 0.92(4) ?
N11 H2N . 0.81(4) ?
N12 C14 . 1.317(7) yes
N12 H3N . 0.84(4) ?
N12 H4N . 0.82(4) ?
C11 C12 . 1.543(6) yes
C12 C13 . 1.543(5) yes
C12 H2A . 0.9800 ?
C13 C14 . 1.522(6) yes
C13 H3A . 0.9700 ?
C13 H3B . 0.9700 ?
O21 C21 . 1.273(6) yes
O22 C21 . 1.222(6) yes
O23 C24 . 1.249(6) yes
N21 C22 . 1.493(6) yes
N21 H5N . 0.90(4) ?
N21 H6N . 0.90(4) ?
N22 C24 . 1.313(7) yes
N22 H7N . 0.86(5) ?
N22 H8N . 0.85(5) ?
C21 C22 . 1.533(6) yes
C22 C23 . 1.501(6) yes
C22 H2B . 0.9800 ?
C23 C24 . 1.511(6) yes
C23 H3C . 0.9700 ?
C23 H3D . 0.9700 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_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
N11 H1N O11 1_655 0.92(4) 2.20(5) 2.987(5) 143(5) yes
N11 H2N O13 . 0.81(4) 2.26(5) 2.944(5) 143(6) yes
N12 H3N O22 2_755 0.84(4) 2.11(5) 2.908(7) 158(7) yes
N12 H4N O11 1_654 0.82(4) 2.49(5) 3.235(5) 151(6) yes
N21 H5N O13 1_456 0.90(4) 2.54(5) 3.135(5) 125(4) yes
N21 H5N O23 . 0.90(4) 2.44(5) 2.975(5) 119(5) yes
N21 H6N O21 1_455 0.90(4) 2.30(5) 3.141(6) 156(6) yes
N22 H7N O12 2_646 0.86(5) 1.97(5) 2.805(6) 165(8) yes
N22 H8N O21 1_456 0.85(5) 2.03(5) 2.830(6) 157(7) yes
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
O21 Cu O11 C11 . 98.0(7)
N11 Cu O11 C11 . 6.3(3)
N21 Cu O11 C11 . 170.4(3)
O23 Cu O11 C11 1_554 -91.6(3)
O11 Cu N11 C12 . -9.9(3)
O21 Cu N11 C12 . -178.7(3)
N21 Cu N11 C12 . -91.6(6)
O23 Cu N11 C12 1_554 86.9(3)
Cu O11 C11 O12 . 178.0(4)
Cu O11 C11 C12 . -1.1(5)
Cu N11 C12 C11 . 11.6(4)
Cu N11 C12 C13 . -109.3(3)
O12 C11 C12 N11 . 173.7(4)
O11 C11 C12 N11 . -7.2(5)
O12 C11 C12 C13 . -62.6(6)
O11 C11 C12 C13 . 116.5(4)
N11 C12 C13 C14 . -55.8(5)
C11 C12 C13 C14 . -178.0(4)
C12 C13 C14 O13 . 73.8(6)
C12 C13 C14 N12 . -107.2(5)
O11 Cu O21 C21 . 71.1(8)
N11 Cu O21 C21 . 161.3(3)
N21 Cu O21 C21 . -2.6(3)
O23 Cu O21 C21 1_554 -99.4(3)
O11 Cu N21 C22 . -147.8(3)
O21 Cu N21 C22 . 21.5(3)
N11 Cu N21 C22 . -67.8(7)
O23 Cu N21 C22 1_554 113.7(3)
Cu O21 C21 O22 . 167.2(4)
Cu O21 C21 C22 . -17.6(5)
Cu N21 C22 C23 . -162.1(3)
Cu N21 C22 C21 . -34.4(4)
O22 C21 C22 N21 . -149.2(4)
O21 C21 C22 N21 . 35.5(5)
O22 C21 C22 C23 . -21.2(6)
O21 C21 C22 C23 . 163.4(4)
N21 C22 C23 C24 . -61.2(5)
C21 C22 C23 C24 . 174.2(4)
Cu O23 C24 N22 1_556 79.4(6)
Cu O23 C24 C23 1_556 -101.9(4)
C22 C23 C24 O23 . -8.7(7)
C22 C23 C24 N22 . 170.2(5)
