#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/10/4311056.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_4311056
loop_
_publ_author_name
'Patrick Deschamps'
'Prasad P. Kulkarni'
'Bibudhendra Sarkar'
_publ_section_title
;
 X-ray Structure of Physiological Copper(II)-Bis(l-histidinato) Complex
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3338
_journal_page_last               3340
_journal_paper_doi               10.1021/ic035413q
_journal_volume                  43
_journal_year                    2004
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C12 H16 Cu N6 O4, 1.5(H2 O)'
_chemical_formula_sum            'C12 H19 Cu N6 O5.5'
_chemical_formula_weight         398.87
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.273(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.9600(2)
_cell_length_b                   11.6650(5)
_cell_length_c                   9.6300(3)
_cell_measurement_reflns_used    6367
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     779.67(5)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'SHELXTL V6.12'
_computing_publication_material  'SHELXTL V6.12'
_computing_structure_refinement  'SHELXTL V6.12(Sheldrick, 2001)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_sigmaI/netI    0.0631
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6417
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.75
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.443
_exptl_absorpt_correction_T_max  0.937
_exptl_absorpt_correction_T_min  0.860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995) 
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.031(14)
_refine_ls_extinction_coef       0.0092(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3183
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0211P)²+0.3256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0779
_reflns_number_gt                2876
_reflns_number_total             3183
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic035413qsi20040420_095550.cif
_cod_data_source_block           k03184
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C12 H19 Cu N6 O5.50'
_cod_database_code               4311056
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.31608(5) 0.89032(4) 0.26600(4) 0.01653(12) Uani 1 1 d . . .
O1 O 0.5908(3) 0.8528(2) 0.2859(2) 0.0186(6) Uani 1 1 d . A .
O2 O 0.8150(3) 0.7518(3) 0.4077(3) 0.0298(6) Uani 1 1 d . A .
O3 O 0.2108(3) 0.7760(2) 0.0842(3) 0.0219(6) Uani 1 1 d . . .
O4 O 0.0341(4) 0.8202(2) -0.1119(3) 0.0278(6) Uani 1 1 d . . .
N1 N 0.3609(4) 1.0223(3) 0.1425(3) 0.0151(6) Uani 1 1 d . A .
N2 N 0.5136(5) 1.1481(3) 0.0221(3) 0.0190(7) Uani 1 1 d . . .
H2B H 0.6076 1.1902 -0.0069 0.023 Uiso 1 1 calc R . .
N3 N 0.0330(4) 0.9231(2) 0.2431(3) 0.0168(7) Uani 1 1 d . A .
H3A H -0.0344 0.8675 0.2866 0.020 Uiso 1 1 calc R . .
H3B H 0.0070 0.9930 0.2820 0.020 Uiso 1 1 calc R . .
C8 C 0.4916(5) 0.7398(4) 0.4771(4) 0.0265(9) Uani 1 1 d . A 1
H8 H 0.5220 0.7803 0.5676 0.032 Uiso 0.50 1 calc PR A 1
N4 N 0.2978(9) 0.7865(6) 0.4253(7) 0.0173(16) Uiso 0.50 1 d P A 1
H4C H 0.2450 0.8253 0.4964 0.021 Uiso 0.50 1 calc PR A 1
H4D H 0.2171 0.7265 0.3992 0.021 Uiso 0.50 1 calc PR A 1
C8* C 0.4916(5) 0.7398(4) 0.4771(4) 0.0265(9) Uani 0.00 1 d P A 2
H8* H 0.4948 0.7868 0.5641 0.032 Uiso 0.50 1 calc PR A 2
N4* N 0.2978(9) 0.7537(6) 0.3956(7) 0.0146(15) Uiso 0.50 1 d P A 2
H4*A H 0.2029 0.7659 0.4555 0.018 Uiso 0.50 1 calc PR A 2
H4*B H 0.2678 0.6885 0.3448 0.018 Uiso 0.50 1 calc PR A 2
C1 C 0.5294(5) 1.0716(3) 0.1249(3) 0.0176(7) Uani 1 1 d . . .
H1A H 0.6459 1.0544 0.1787 0.021 Uiso 1 1 calc R A .
C2 C 0.3249(5) 1.1495(3) -0.0306(3) 0.0184(7) Uani 1 1 d . . .
H2A H 0.2715 1.1959 -0.1048 0.022 Uiso 1 1 calc R A .
C3 C 0.2287(5) 1.0718(3) 0.0437(3) 0.0159(7) Uani 1 1 d . A .
C4 C 0.0194(5) 1.0421(3) 0.0323(3) 0.0187(7) Uani 1 1 d . . .
H4A H -0.0287 1.0441 -0.0671 0.022 Uiso 1 1 calc R A .
H4B H -0.0516 1.1011 0.0818 0.022 Uiso 1 1 calc R . .
C5 C -0.0242(5) 0.9243(3) 0.0922(3) 0.0169(7) Uani 1 1 d . A .
H5A H -0.1660 0.9102 0.0783 0.020 Uiso 1 1 calc R . .
C6 C 0.0801(5) 0.8319(3) 0.0155(3) 0.0178(7) Uani 1 1 d . . .
C7 C 0.6459(5) 0.7830(3) 0.3837(4) 0.0216(8) Uani 1 1 d . . .
C9 C 0.5092(6) 0.6126(4) 0.5145(4) 0.0265(8) Uani 1 1 d DU A 1
H9A H 0.6454 0.5941 0.5424 0.032 Uiso 1 1 calc R A 1
H9B H 0.4319 0.5961 0.5944 0.032 Uiso 1 1 calc R A 1
N5 N 0.5748(16) 0.5101(8) 0.3073(9) 0.020(2) Uani 0.465(15) 1 d P A 1
N6 N 0.2908(18) 0.4365(9) 0.2448(12) 0.025(2) Uani 0.465(15) 1 d P A 1
H6 H 0.2007 0.3980 0.1956 0.030 Uiso 0.465(15) 1 calc PR A 1
C10 C 0.4398(18) 0.5393(9) 0.3927(8) 0.0269(11) Uani 0.465(15) 1 d PDU A 1
C11 C 0.2650(19) 0.4994(11) 0.3637(13) 0.022(3) Uani 0.465(15) 1 d P A 1
H11A H 0.1518 0.5107 0.4114 0.026 Uiso 0.465(15) 1 calc PR A 1
C12 C 0.473(3) 0.4440(10) 0.2176(10) 0.022(3) Uani 0.465(15) 1 d P A 1
H12A H 0.5257 0.4060 0.1419 0.027 Uiso 0.465(15) 1 calc PR A 1
C9* C 0.5092(6) 0.6126(4) 0.5145(4) 0.0265(8) Uani 0.00 1 d P A 2
H9C H 0.6305 0.6015 0.5733 0.032 Uiso 0.00 1 calc PR A 2
H9D H 0.4016 0.5924 0.5716 0.032 Uiso 0.00 1 calc PR A 2
N5* N 0.3345(14) 0.4821(8) 0.3285(10) 0.024(2) Uani 0.535(15) 1 d P A 2
N6* N 0.5744(17) 0.4053(9) 0.2197(6) 0.032(2) Uani 0.535(15) 1 d P A 2
H6* H 0.6361 0.3635 0.1613 0.039 Uiso 0.535(15) 1 calc PR A 2
C10* C 0.5078(16) 0.5301(7) 0.3945(8) 0.0263(11) Uani 0.535(15) 1 d PDU A 2
C11* C 0.6559(18) 0.4782(9) 0.3225(10) 0.025(2) Uani 0.535(15) 1 d P A 2
H11B H 0.7900 0.4912 0.3415 0.030 Uiso 0.535(15) 1 calc PR A 2
C12* C 0.382(3) 0.4116(11) 0.2276(10) 0.029(3) Uani 0.535(15) 1 d P A 2
H12B H 0.2908 0.3706 0.1683 0.034 Uiso 0.535(15) 1 calc PR A 2
O1W O -0.0423(5) 1.1722(3) 0.3492(3) 0.0379(8) Uani 1 1 d . . .
H1WA H -0.033(7) 1.218(5) 0.274(5) 0.046(14) Uiso 1 1 d . . .
H1WB H 0.023(9) 1.198(5) 0.406(6) 0.07(2) Uiso 1 1 d . . .
O2W O 0.9500(8) 0.4578(6) 0.4392(6) 0.0377(15) Uani 0.50 1 d P . .
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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
Cu Cu 0.3201 1.2651 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N4 84.6(2) . . ?
O1 Cu1 N1 92.08(10) . . ?
N4 Cu1 N1 165.4(2) . . ?
O1 Cu1 N3 177.96(12) . . ?
N4 Cu1 N3 94.8(2) . . ?
N1 Cu1 N3 89.03(11) . . ?
O1 Cu1 N4* 82.52(18) . . ?
N4 Cu1 N4* 13.6(2) . . ?
N1 Cu1 N4* 174.56(19) . . ?
N3 Cu1 N4* 96.39(19) . . ?
O1 Cu1 O3 101.54(9) . . ?
N4 Cu1 O3 101.7(2) . . ?
N1 Cu1 O3 92.85(11) . . ?
N3 Cu1 O3 76.69(10) . . ?
N4* Cu1 O3 88.9(2) . . ?
C7 O1 Cu1 116.8(2) . . ?
C6 O3 Cu1 106.1(2) . . ?
C1 N1 C3 106.1(3) . . ?
C1 N1 Cu1 126.3(2) . . ?
C3 N1 Cu1 127.1(2) . . ?
C1 N2 C2 107.9(3) . . ?
C5 N3 Cu1 107.47(19) . . ?
N4 C8 C9 118.8(4) . . ?
N4 C8 C7 109.6(4) . . ?
C9 C8 C7 114.1(3) . . ?
C8 N4 Cu1 111.9(4) . . ?
N1 C1 N2 111.1(3) . . ?
C3 C2 N2 107.0(3) . . ?
C2 C3 N1 107.9(3) . . ?
C2 C3 C4 129.1(3) . . ?
N1 C3 C4 122.9(3) . . ?
C3 C4 C5 113.6(3) . . ?
N3 C5 C6 111.6(3) . . ?
N3 C5 C4 109.5(3) . . ?
C6 C5 C4 109.8(3) . . ?
O4 C6 O3 125.3(3) . . ?
O4 C6 C5 117.2(3) . . ?
O3 C6 C5 117.5(3) . . ?
O2 C7 O1 123.6(3) . . ?
O2 C7 C8 119.4(3) . . ?
O1 C7 C8 117.0(3) . . ?
C10 C9 C8 110.7(5) . . ?
C12 N5 C10 100.6(9) . . ?
C12 N6 C11 108.4(9) . . ?
C11 C10 N5 117.4(8) . . ?
C11 C10 C9 127.4(9) . . ?
N5 C10 C9 115.2(8) . . ?
C10 C11 N6 100.9(9) . . ?
N6 C12 N5 112.7(9) . . ?
C12* N5* C10* 108.6(8) . . ?
C12* N6* C11* 106.2(8) . . ?
C11* C10* N5* 103.5(6) . . ?
N6* C11* C10* 109.6(8) . . ?
N5* C12* N6* 112.0(10) . . ?
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
Cu1 O1 1.957(2) . ?
Cu1 N4 1.966(6) . ?
Cu1 N1 1.984(3) . ?
Cu1 N3 2.003(3) . ?
Cu1 N4* 2.034(6) . ?
Cu1 O3 2.277(2) . ?
O1 C7 1.282(4) . ?
O2 C7 1.237(4) . ?
O3 C6 1.266(4) . ?
O4 C6 1.251(4) . ?
N1 C1 1.328(4) . ?
N1 C3 1.398(4) . ?
N2 C1 1.331(5) . ?
N2 C2 1.373(5) . ?
N3 C5 1.478(4) . ?
C8 N4 1.505(7) . ?
C8 C9 1.530(6) . ?
C8 C7 1.536(5) . ?
C2 C3 1.361(5) . ?
C3 C4 1.493(5) . ?
C4 C5 1.529(5) . ?
C5 C6 1.521(5) . ?
C9 C10 1.501(7) . ?
N5 C12 1.323(14) . ?
N5 C10 1.339(12) . ?
N6 C12 1.317(13) . ?
N6 C11 1.383(15) . ?
C10 C11 1.313(14) . ?
N5* C12* 1.333(14) . ?
N5* C10* 1.435(11) . ?
N6* C12* 1.350(14) . ?
N6* C11* 1.394(11) . ?
C10* C11* 1.420(11) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A O2 0.92 2.11 3.028(4) 173.2 1_455
N3 H3B O1W 0.92 2.22 3.137(5) 172.1 .
O1W H1WA O4 0.90(5) 1.97(5) 2.869(4) 176(4) 2
O1W H1WB O2 0.75(6) 2.14(6) 2.879(4) 170(6) 2_656
N2 H2B O3 0.88 1.82 2.692(4) 174.2 2_655
