#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/36/2223674.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_2223674
loop_
_publ_author_name
'Chen, Li-Hua'
'Zhao, Gan-Qing'
'Wang, Xiang'
'Peng, Qin-Long'
'Pan, Zi-Hong'
_publ_section_title
;
 (2-Acetylphenolato)(2,2'-bipyridine)nitratocopper(II)
;
_journal_coeditor_code           CI2918
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1427
_journal_paper_doi               10.1107/S1600536809042718
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Cu (C8 H7 O2) (N O3) (C10 H8 N2)]'
_chemical_formula_moiety         '[Cu(C8 H7 O2)(C10 H8 N2)(N O3)]'
_chemical_formula_sum            'C18 H15 Cu N3 O5'
_chemical_formula_weight         416.87
_chemical_name_systematic
;
(2-Acetylphenolato)(2,2'-bipyridine)nitratocopper(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 108.5830(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4683(12)
_cell_length_b                   8.3101(8)
_cell_length_c                   15.5924(15)
_cell_measurement_reflns_used    3127
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.97
_cell_measurement_theta_min      2.42
_cell_volume                     1654.2(3)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8261
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.42
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.358
_exptl_absorpt_correction_T_max  0.7728
_exptl_absorpt_correction_T_min  0.6860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.271
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2917
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0290
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0308P)²+0.9795P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0735
_reflns_number_gt                2370
_reflns_number_total             2917
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2918.cif
_cod_data_source_block           I
_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 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2223674
_cod_database_fobs_code          2223674
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'
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 0.77943(2) 0.96237(4) 0.03090(2) 0.03038(11) Uani d . 1 . .
C C1 0.7404(2) 1.1660(3) 0.17445(18) 0.0395(7) Uani d . 1 . .
H H1 0.8040 1.1268 0.2122 0.047 Uiso calc R 1 . .
C C2 0.6852(2) 1.2727(4) 0.20915(19) 0.0453(7) Uani d . 1 . .
H H2 0.7101 1.3038 0.2696 0.054 Uiso calc R 1 . .
C C3 0.5919(2) 1.3328(4) 0.1521(2) 0.0473(7) Uani d . 1 . .
H H3 0.5538 1.4070 0.1735 0.057 Uiso calc R 1 . .
C C4 0.5554(2) 1.2825(3) 0.06330(19) 0.0400(7) Uani d . 1 . .
H H4 0.4924 1.3216 0.0245 0.048 Uiso calc R 1 . .
C C5 0.61386(18) 1.1732(3) 0.03286(16) 0.0300(6) Uani d . 1 . .
C C6 0.58213(18) 1.1050(3) -0.05922(16) 0.0292(6) Uani d . 1 . .
C C7 0.4907(2) 1.1450(3) -0.12742(17) 0.0377(6) Uani d . 1 . .
H H7 0.4449 1.2210 -0.1174 0.045 Uiso calc R 1 . .
C C8 0.4688(2) 1.0699(3) -0.21052(18) 0.0418(7) Uani d . 1 . .
H H8 0.4079 1.0951 -0.2572 0.050 Uiso calc R 1 . .
C C9 0.5378(2) 0.9575(3) -0.22366(17) 0.0376(6) Uani d . 1 . .
H H9 0.5242 0.9058 -0.2791 0.045 Uiso calc R 1 . .
C C10 0.6270(2) 0.9231(3) -0.15362(17) 0.0352(6) Uani d . 1 . .
H H10 0.6733 0.8467 -0.1623 0.042 Uiso calc R 1 . .
C C11 0.99646(19) 0.9179(3) 0.13299(17) 0.0324(6) Uani d . 1 . .
C C12 1.08113(19) 0.9544(3) 0.21194(18) 0.0378(6) Uani d . 1 . .
H H12 1.0700 1.0212 0.2559 0.045 Uiso calc R 1 . .
C C13 1.1790(2) 0.8929(4) 0.2243(2) 0.0441(7) Uani d . 1 . .
H H13 1.2334 0.9192 0.2764 0.053 Uiso calc R 1 . .
C C14 1.1984(2) 0.7920(3) 0.1607(2) 0.0443(7) Uani d . 1 . .
H H14 1.2647 0.7482 0.1711 0.053 Uiso calc R 1 . .
C C15 1.11933(19) 0.7571(3) 0.08252(19) 0.0384(6) Uani d . 1 . .
H H15 1.1331 0.6919 0.0392 0.046 Uiso calc R 1 . .
C C16 1.01667(18) 0.8190(3) 0.06647(17) 0.0306(6) Uani d . 1 . .
C C17 0.93694(19) 0.7830(3) -0.01883(17) 0.0309(6) Uani d . 1 . .
C C18 0.9599(2) 0.6816(3) -0.08916(19) 0.0445(7) Uani d . 1 . .
H H18A 0.8996 0.6788 -0.1425 0.067 Uiso calc R 1 . .
H H18B 0.9769 0.5743 -0.0664 0.067 Uiso calc R 1 . .
H H18C 1.0182 0.7265 -0.1039 0.067 Uiso calc R 1 . .
N N1 0.70583(15) 1.1164(2) 0.08838(13) 0.0309(5) Uani d . 1 . .
N N2 0.64940(15) 0.9956(2) -0.07351(13) 0.0285(5) Uani d . 1 . .
N N3 0.73727(19) 0.5847(3) 0.03372(17) 0.0450(6) Uani d . 1 . .
O O1 0.90495(13) 0.9788(2) 0.12828(12) 0.0381(4) Uani d . 1 . .
O O2 0.84484(12) 0.8358(2) -0.04004(11) 0.0332(4) Uani d . 1 . .
O O3 0.70722(15) 0.7105(2) 0.06448(14) 0.0491(5) Uani d . 1 . .
O O4 0.6824(2) 0.5290(3) -0.03905(18) 0.0818(8) Uani d . 1 . .
O O5 0.8215(2) 0.5239(3) 0.07571(19) 0.0848(9) Uani d . 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'
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Cu1 O2 . . 92.60(7) ?
O1 Cu1 N2 . . 167.80(8) ?
O2 Cu1 N2 . . 92.87(8) ?
O1 Cu1 N1 . . 92.18(8) ?
O2 Cu1 N1 . . 171.30(8) ?
N2 Cu1 N1 . . 81.10(8) ?
O1 Cu1 O3 . . 101.92(8) ?
O2 Cu1 O3 . . 86.63(7) ?
N2 Cu1 O3 . . 89.28(7) ?
N1 Cu1 O3 . . 99.49(7) ?
N1 C1 C2 . . 122.4(3) ?
N1 C1 H1 . . 118.8 ?
C2 C1 H1 . . 118.8 ?
C1 C2 C3 . . 118.3(3) ?
C1 C2 H2 . . 120.8 ?
C3 C2 H2 . . 120.8 ?
C4 C3 C2 . . 119.8(3) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C3 C4 C5 . . 119.0(3) ?
C3 C4 H4 . . 120.5 ?
C5 C4 H4 . . 120.5 ?
N1 C5 C4 . . 121.1(2) ?
N1 C5 C6 . . 114.3(2) ?
C4 C5 C6 . . 124.6(2) ?
N2 C6 C7 . . 120.9(2) ?
N2 C6 C5 . . 114.7(2) ?
C7 C6 C5 . . 124.4(2) ?
C8 C7 C6 . . 118.8(2) ?
C8 C7 H7 . . 120.6 ?
C6 C7 H7 . . 120.6 ?
C9 C8 C7 . . 119.5(2) ?
C9 C8 H8 . . 120.2 ?
C7 C8 H8 . . 120.2 ?
C10 C9 C8 . . 118.9(3) ?
C10 C9 H9 . . 120.5 ?
C8 C9 H9 . . 120.5 ?
N2 C10 C9 . . 122.1(2) ?
N2 C10 H10 . . 118.9 ?
C9 C10 H10 . . 118.9 ?
O1 C11 C16 . . 125.4(2) ?
O1 C11 C12 . . 116.5(2) ?
C16 C11 C12 . . 118.1(2) ?
C13 C12 C11 . . 120.9(3) ?
C13 C12 H12 . . 119.5 ?
C11 C12 H12 . . 119.5 ?
C12 C13 C14 . . 121.2(3) ?
C12 C13 H13 . . 119.4 ?
C14 C13 H13 . . 119.4 ?
C15 C14 C13 . . 119.6(3) ?
C15 C14 H14 . . 120.2 ?
C13 C14 H14 . . 120.2 ?
C14 C15 C16 . . 121.1(3) ?
C14 C15 H15 . . 119.4 ?
C16 C15 H15 . . 119.4 ?
C11 C16 C15 . . 119.0(2) ?
C11 C16 C17 . . 122.2(2) ?
C15 C16 C17 . . 118.8(2) ?
O2 C17 C16 . . 123.4(2) ?
O2 C17 C18 . . 115.0(2) ?
C16 C17 C18 . . 121.6(2) ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C1 N1 C5 . . 119.3(2) ?
C1 N1 Cu1 . . 125.73(18) ?
C5 N1 Cu1 . . 114.92(16) ?
C10 N2 C6 . . 119.7(2) ?
C10 N2 Cu1 . . 125.48(17) ?
C6 N2 Cu1 . . 114.78(16) ?
O5 N3 O4 . . 121.3(3) ?
O5 N3 O3 . . 119.4(3) ?
O4 N3 O3 . . 119.2(3) ?
C11 O1 Cu1 . . 127.05(16) ?
C17 O2 Cu1 . . 129.18(16) ?
N3 O3 Cu1 . . 115.43(16) ?
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 O1 . 1.8832(17) y
Cu1 O2 . 1.9307(17) y
Cu1 N2 . 1.9941(19) y
Cu1 N1 . 1.998(2) y
Cu1 O3 . 2.434(2) y
C1 N1 . 1.338(3) ?
C1 C2 . 1.374(4) ?
C1 H1 . 0.93 ?
C2 C3 . 1.381(4) ?
C2 H2 . 0.93 ?
C3 C4 . 1.378(4) ?
C3 H3 . 0.93 ?
C4 C5 . 1.381(4) ?
C4 H4 . 0.93 ?
C5 N1 . 1.350(3) ?
C5 C6 . 1.474(3) ?
C6 N2 . 1.351(3) ?
C6 C7 . 1.387(3) ?
C7 C8 . 1.383(4) ?
C7 H7 . 0.93 ?
C8 C9 . 1.379(4) ?
C8 H8 . 0.93 ?
C9 C10 . 1.371(3) ?
C9 H9 . 0.93 ?
C10 N2 . 1.332(3) ?
C10 H10 . 0.93 ?
C11 O1 . 1.313(3) ?
C11 C16 . 1.416(4) ?
C11 C12 . 1.419(3) ?
C12 C13 . 1.369(4) ?
C12 H12 . 0.93 ?
C13 C14 . 1.386(4) ?
C13 H13 . 0.93 ?
C14 C15 . 1.370(4) ?
C14 H14 . 0.93 ?
C15 C16 . 1.421(3) ?
C15 H15 . 0.93 ?
C16 C17 . 1.450(3) ?
C17 O2 . 1.256(3) ?
C17 C18 . 1.492(4) ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?
N3 O5 . 1.224(3) ?
N3 O4 . 1.230(3) ?
N3 O3 . 1.269(3) ?
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
C2 H2 O3 2_655 0.93 2.59 3.401(4) 146
C7 H7 O3 3_675 0.93 2.51 3.343(3) 150
