#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/50/2225010.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_2225010
loop_
_publ_author_name
'Thiam, Ibrahima Elhadj'
'Retailleau, Pascal'
'Navaza, Alda'
'Gaye, Mohamed'
_publ_section_title
;{2-[(2-Acetylhydrazin-1-ylidene)methyl-κ²N¹,O]-6-methoxyphenolato-κO¹}(nitrato-κO)copper(II)
 monohydrate
;
_journal_coeditor_code           HY2267
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m136
_journal_paper_doi               10.1107/S1600536810000632
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Cu (C10 H11 N2 O3) (N O3)] , H2 O'
_chemical_formula_moiety         'C10 H11 Cu N3 O6 , H2 O'
_chemical_formula_sum            'C10 H13 Cu N3 O7'
_chemical_formula_weight         350.77
_chemical_melting_point          469
_chemical_name_systematic
;
{2-[(2-Acetylhydrazin-1-ylidene)methyl-κ²N¹,O]-
6-methoxyphenolato-κO¹}(nitrato-κO)copper(II) monohydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.16(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.274(2)
_cell_length_b                   10.455(4)
_cell_length_c                   13.726(4)
_cell_measurement_reflns_used    12725
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1325.5(7)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5500
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    1.687
_exptl_absorpt_correction_T_max  0.72
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(DENZO/SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.443
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3046
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0330
_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)+(0.0515P)²+0.2512P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0897
_reflns_number_gt                2493
_reflns_number_total             3046
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hy2267.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225010
_cod_database_fobs_code          2225010
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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
Cu Cu1 0.09934(3) 0.23847(2) 0.104081(19) 0.03448(11) Uani d . 1 . .
O O1 0.20916(16) 0.08774(13) 0.10007(12) 0.0391(3) Uani d . 1 . .
O O2 0.39441(16) -0.09065(15) 0.07532(13) 0.0489(4) Uani d . 1 . .
O O3 -0.02563(16) 0.38826(14) 0.12039(12) 0.0417(4) Uani d . 1 . .
O O4 0.25659(17) 0.34556(16) 0.06197(12) 0.0464(4) Uani d . 1 . .
O O5 0.40681(19) 0.48337(19) 0.13003(19) 0.0784(7) Uani d . 1 . .
O O6 0.2791(2) 0.3648(2) 0.21931(14) 0.0662(5) Uani d . 1 . .
O O7 -0.45344(19) 0.13264(18) 0.18452(13) 0.0589(5) Uani d . 1 . .
H H1O -0.5371 0.1148 0.1455 0.071 Uiso d R 1 . .
H H2O -0.4318 0.0772 0.2358 0.071 Uiso d R 1 . .
N N1 -0.07247(18) 0.14998(17) 0.13266(12) 0.0321(4) Uani d . 1 . .
N N2 -0.1848(2) 0.23436(17) 0.14647(14) 0.0362(4) Uani d . 1 . .
H H2N -0.2694 0.2092 0.1591 0.043 Uiso calc R 1 . .
N N3 0.31622(19) 0.39954(18) 0.13960(18) 0.0477(5) Uani d . 1 . .
C C1 0.1588(2) -0.02931(19) 0.10347(14) 0.0323(4) Uani d . 1 . .
C C2 0.0145(2) -0.0638(2) 0.11923(14) 0.0336(4) Uani d . 1 . .
C C3 -0.0258(3) -0.1947(2) 0.11989(16) 0.0404(5) Uani d . 1 . .
H H3 -0.1210 -0.2163 0.1288 0.048 Uiso calc R 1 . .
C C4 0.0720(3) -0.2894(2) 0.10779(16) 0.0435(5) Uani d . 1 . .
H H4 0.0438 -0.3747 0.1087 0.052 Uiso calc R 1 . .
C C5 0.2160(3) -0.2570(2) 0.09391(17) 0.0405(5) Uani d . 1 . .
H H5 0.2833 -0.3214 0.0865 0.049 Uiso calc R 1 . .
C C6 0.2581(2) -0.1313(2) 0.09123(15) 0.0351(4) Uani d . 1 . .
C C7 -0.0955(2) 0.0287(2) 0.13384(15) 0.0360(5) Uani d . 1 . .
H H7 -0.1876 -0.0002 0.1447 0.043 Uiso calc R 1 . .
C C8 0.5026(3) -0.1853(3) 0.0650(2) 0.0549(6) Uani d . 1 . .
H H8A 0.5203 -0.2318 0.1251 0.082 Uiso calc R 1 . .
H H8B 0.5904 -0.1446 0.0494 0.082 Uiso calc R 1 . .
H H8C 0.4699 -0.2432 0.0134 0.082 Uiso calc R 1 . .
C C9 -0.1505(2) 0.3575(2) 0.13847(15) 0.0371(5) Uani d . 1 . .
C C10 -0.2645(3) 0.4550(2) 0.14953(19) 0.0504(6) Uani d . 1 . .
H H10A -0.2274 0.5200 0.1944 0.076 Uiso calc R 1 . .
H H10B -0.3470 0.4149 0.1742 0.076 Uiso calc R 1 . .
H H10C -0.2929 0.4931 0.0871 0.076 Uiso calc R 1 . .
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'
Cu Cu 0.3201 1.2651 '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 0.0060 '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
O1 Cu1 N1 . . 93.67(7) ?
O1 Cu1 O4 . . 92.90(7) ?
N1 Cu1 O4 . . 171.47(7) ?
O1 Cu1 O3 . . 173.76(6) ?
N1 Cu1 O3 . . 81.49(7) ?
O4 Cu1 O3 . . 92.30(7) ?
O1 Cu1 O6 . . 97.25(7) ?
O3 Cu1 O6 . . 82.93(7) ?
O4 Cu1 O6 . . 55.16(7) ?
N1 Cu1 O6 . . 129.12(7) ?
C1 O1 Cu1 . . 125.84(13) ?
C6 O2 C8 . . 117.93(18) ?
C9 O3 Cu1 . . 112.53(14) ?
N3 O4 Cu1 . . 106.34(13) ?
H1O O7 H2O . . 115.6 ?
C7 N1 N2 . . 119.75(18) ?
C7 N1 Cu1 . . 128.43(15) ?
N2 N1 Cu1 . . 111.66(13) ?
C9 N2 N1 . . 114.45(17) ?
C9 N2 H2N . . 122.8 ?
N1 N2 H2N . . 122.8 ?
O5 N3 O6 . . 123.6(2) ?
O5 N3 O4 . . 118.1(2) ?
O6 N3 O4 . . 118.24(19) ?
O1 C1 C2 . . 125.80(19) ?
O1 C1 C6 . . 117.19(18) ?
C2 C1 C6 . . 117.01(18) ?
C3 C2 C1 . . 119.86(19) ?
C3 C2 C7 . . 117.3(2) ?
C1 C2 C7 . . 122.82(19) ?
C4 C3 C2 . . 121.4(2) ?
C4 C3 H3 . . 119.3 ?
C2 C3 H3 . . 119.3 ?
C3 C4 C5 . . 119.5(2) ?
C3 C4 H4 . . 120.3 ?
C5 C4 H4 . . 120.3 ?
C6 C5 C4 . . 120.7(2) ?
C6 C5 H5 . . 119.7 ?
C4 C5 H5 . . 119.7 ?
O2 C6 C5 . . 124.8(2) ?
O2 C6 C1 . . 113.64(18) ?
C5 C6 C1 . . 121.6(2) ?
N1 C7 C2 . . 122.85(19) ?
N1 C7 H7 . . 118.6 ?
C2 C7 H7 . . 118.6 ?
O2 C8 H8A . . 109.5 ?
O2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O3 C9 N2 . . 119.85(19) ?
O3 C9 C10 . . 121.7(2) ?
N2 C9 C10 . . 118.4(2) ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
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
Cu1 N1 . 1.9134(18) y
Cu1 O1 . 1.8798(15) y
Cu1 O3 . 1.9730(16) y
Cu1 O4 . 1.9663(16) y
Cu1 O6 . 2.559(2) y
O1 C1 . 1.312(2) ?
O2 C6 . 1.370(3) ?
O2 C8 . 1.425(3) ?
O3 C9 . 1.248(3) ?
O4 N3 . 1.286(3) ?
O5 N3 . 1.229(3) ?
O6 N3 . 1.231(3) ?
O7 H1O . 0.92 ?
O7 H2O . 0.92 ?
N1 C7 . 1.286(3) ?
N1 N2 . 1.391(2) ?
N2 C9 . 1.333(3) ?
N2 H2N . 0.8600 ?
C1 C2 . 1.422(3) ?
C1 C6 . 1.428(3) ?
C2 C3 . 1.419(3) ?
C2 C7 . 1.433(3) ?
C3 C4 . 1.363(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.407(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.373(3) ?
C5 H5 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 C10 . 1.486(3) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
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
N2 H2N O7 . 0.86 1.95 2.801(3) 174
O7 H1O O1 1_455 0.92 2.40 3.271(3) 159
O7 H1O O2 1_455 0.92 2.42 3.050(3) 126
O7 H2O O5 2_545 0.92 2.08 2.984(3) 167
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
N1 Cu1 O1 C1 . . . . 7.99(17) ?
O4 Cu1 O1 C1 . . . . -166.57(17) ?
N1 Cu1 O3 C9 . . . . -1.29(15) ?
O4 Cu1 O3 C9 . . . . 172.83(15) ?
O1 Cu1 O4 N3 . . . . -101.08(13) ?
O3 Cu1 O4 N3 . . . . 75.48(14) ?
O1 Cu1 N1 C7 . . . . -7.63(19) ?
O3 Cu1 N1 C7 . . . . 176.33(18) ?
O1 Cu1 N1 N2 . . . . 177.15(13) ?
O3 Cu1 N1 N2 . . . . 1.11(13) ?
C7 N1 N2 C9 . . . . -176.51(19) ?
Cu1 N1 N2 C9 . . . . -0.8(2) ?
Cu1 O4 N3 O5 . . . . -171.45(16) ?
Cu1 O4 N3 O6 . . . . 8.3(2) ?
Cu1 O1 C1 C2 . . . . -5.8(3) ?
Cu1 O1 C1 C6 . . . . 174.91(14) ?
O1 C1 C2 C3 . . . . 179.18(19) ?
C6 C1 C2 C3 . . . . -1.5(3) ?
O1 C1 C2 C7 . . . . -0.1(3) ?
C6 C1 C2 C7 . . . . 179.19(18) ?
C1 C2 C3 C4 . . . . 1.5(3) ?
C7 C2 C3 C4 . . . . -179.2(2) ?
C2 C3 C4 C5 . . . . -0.3(3) ?
C3 C4 C5 C6 . . . . -0.8(4) ?
C8 O2 C6 C5 . . . . -2.9(3) ?
C8 O2 C6 C1 . . . . 178.26(19) ?
C4 C5 C6 O2 . . . . -178.0(2) ?
C4 C5 C6 C1 . . . . 0.7(3) ?
O1 C1 C6 O2 . . . . -1.3(3) ?
C2 C1 C6 O2 . . . . 179.32(18) ?
O1 C1 C6 C5 . . . . 179.8(2) ?
C2 C1 C6 C5 . . . . 0.4(3) ?
N2 N1 C7 C2 . . . . 179.38(18) ?
Cu1 N1 C7 C2 . . . . 4.5(3) ?
C3 C2 C7 N1 . . . . -178.50(19) ?
C1 C2 C7 N1 . . . . 0.8(3) ?
Cu1 O3 C9 N2 . . . . 1.2(3) ?
Cu1 O3 C9 C10 . . . . -177.50(16) ?
N1 N2 C9 O3 . . . . -0.3(3) ?
N1 N2 C9 C10 . . . . 178.48(18) ?
