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#$Date: 2022-05-17 12:06:32 +0300 (Tue, 17 May 2022) $
#$Revision: 275486 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/52/8105283.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_8105283
loop_
_publ_author_name
'Guo, Xiao-Yu'
'Chen, Ji-Hong'
'Meng, Xiang-Ru'
_publ_section_title
;
 Crystal structure of
 catena-poly[aqua[(μ2-4,5-dicarboxylato-2-(2-carboxylatophenyl)imidazol-1-ido-κ4
 N,O,O′:N′)](μ2-4,4′-bipyridine-κ2
 N:N′)dicopper(II)], C22H14Cu2N4O7
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              771
_journal_page_last               773
_journal_paper_doi               10.1515/ncrs-2019-0887
_journal_volume                  235
_journal_year                    2020
_chemical_formula_sum            'C22 H14 Cu2 N4 O7'
_chemical_formula_weight         573.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 102.184(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7885(4)
_cell_length_b                   14.9974(8)
_cell_length_c                   17.7464(10)
_cell_measurement_reflns_used    9995
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.69
_cell_volume                     2026.22(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18388
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.559
_diffrn_reflns_theta_min         2.685
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Bruker 2000)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.880
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_exptl_transmission_factor_max   0.7456
_exptl_transmission_factor_min   0.6354
_refine_diff_density_max         0.677
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4590
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0432P)²+1.9504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0936
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3501
_reflns_number_total             4590
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0887_suppl.cif
_cod_data_source_block           exp_I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8105283
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.685
_shelx_estimated_absorpt_t_max   0.752
loop_
_space_group_symop_operation_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_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu -0.01549(5) 0.78163(2) 0.40649(2) 0.03277(12) Uani 1 1 d . . . . .
Cu2 Cu 0.36285(5) 0.43343(2) 0.42669(2) 0.03650(12) Uani 1 1 d . . . . .
N1 N 0.1042(3) 0.66840(14) 0.42948(13) 0.0269(5) Uani 1 1 d . . . . .
N2 N 0.2469(3) 0.53878(14) 0.44283(13) 0.0266(5) Uani 1 1 d . . . . .
N3 N 0.4722(3) 0.32443(15) 0.41233(14) 0.0321(5) Uani 1 1 d . . . . .
N4 N 0.8689(3) -0.09902(15) 0.40118(16) 0.0368(6) Uani 1 1 d . . . . .
O1 O -0.0601(3) 0.75939(13) 0.51917(13) 0.0415(5) Uani 1 1 d . . . . .
O2 O -0.0101(3) 0.65640(15) 0.61277(13) 0.0457(6) Uani 1 1 d . . . . .
O3 O 0.1658(3) 0.51509(15) 0.63626(12) 0.0432(5) Uani 1 1 d . . . . .
O4 O 0.3074(3) 0.42437(14) 0.57187(13) 0.0430(5) Uani 1 1 d . . . . .
O5 O 0.1576(3) 0.82396(14) 0.34898(16) 0.0524(7) Uani 1 1 d . . . . .
O6 O 0.4416(3) 0.82363(16) 0.35081(16) 0.0536(6) Uani 1 1 d . . . . .
O7 O -0.2564(3) 0.72464(14) 0.33902(13) 0.0439(5) Uani 1 1 d . . . . .
H7A H -0.351604 0.754206 0.331865 0.066 Uiso 1 1 d R U . . .
H7B H -0.280104 0.673136 0.354035 0.066 Uiso 1 1 d R U . . .
C1 C 0.0032(4) 0.68709(19) 0.54818(18) 0.0326(6) Uani 1 1 d . . . . .
C2 C 0.0993(4) 0.63460(17) 0.50043(15) 0.0259(6) Uani 1 1 d . . . . .
C3 C 0.1872(3) 0.55490(16) 0.50921(16) 0.0254(6) Uani 1 1 d . . . . .
C4 C 0.2246(4) 0.49292(19) 0.57514(17) 0.0330(7) Uani 1 1 d . . . . .
C5 C 0.1933(4) 0.60918(16) 0.39632(16) 0.0265(6) Uani 1 1 d . . . . .
C6 C 0.2300(4) 0.61848(19) 0.31925(18) 0.0348(7) Uani 1 1 d . . . . .
C7 C 0.2224(5) 0.5421(2) 0.2728(2) 0.0494(9) Uani 1 1 d . . . . .
H7 H 0.185955 0.488332 0.290213 0.059 Uiso 1 1 calc R U . . .
C8 C 0.2675(6) 0.5453(3) 0.2022(2) 0.0632(11) Uani 1 1 d . . . . .
H8 H 0.259577 0.494543 0.171577 0.076 Uiso 1 1 calc R U . . .
C9 C 0.3253(6) 0.6257(3) 0.1769(2) 0.0615(11) Uani 1 1 d . . . . .
H9 H 0.359103 0.628172 0.129695 0.074 Uiso 1 1 calc R U . . .
C10 C 0.3329(5) 0.7016(2) 0.2213(2) 0.0494(9) Uani 1 1 d . . . . .
H10 H 0.372511 0.754673 0.203829 0.059 Uiso 1 1 calc R U . . .
C11 C 0.2818(4) 0.6998(2) 0.29220(18) 0.0364(7) Uani 1 1 d . . . . .
C12 C 0.2943(4) 0.7878(2) 0.33492(19) 0.0386(7) Uani 1 1 d . . . . .
C13 C 0.5415(4) 0.30177(19) 0.35193(18) 0.0353(7) Uani 1 1 d . . . . .
H13 H 0.536393 0.343010 0.312382 0.042 Uiso 1 1 calc R U . . .
C14 C 0.6200(4) 0.22033(18) 0.34544(18) 0.0355(7) Uani 1 1 d . . . . .
H14 H 0.666890 0.207766 0.302558 0.043 Uiso 1 1 calc R U . . .
C15 C 0.6284(4) 0.15751(18) 0.40343(17) 0.0305(6) Uani 1 1 d . . . . .
C16 C 0.5568(4) 0.18153(19) 0.46574(18) 0.0377(7) Uani 1 1 d . . . . .
H16 H 0.559744 0.141512 0.506027 0.045 Uiso 1 1 calc R U . . .
C17 C 0.4817(4) 0.26390(19) 0.46837(19) 0.0382(7) Uani 1 1 d . . . . .
H17 H 0.435270 0.278263 0.511013 0.046 Uiso 1 1 calc R U . . .
C18 C 0.7098(4) 0.06840(18) 0.40097(17) 0.0327(6) Uani 1 1 d . . . . .
C19 C 0.7574(5) 0.0344(2) 0.3368(2) 0.0550(10) Uani 1 1 d . . . . .
H19 H 0.736626 0.067044 0.291217 0.066 Uiso 1 1 calc R U . . .
C20 C 0.8361(6) -0.0485(2) 0.3395(2) 0.0571(11) Uani 1 1 d . . . . .
H20 H 0.867711 -0.069565 0.295059 0.069 Uiso 1 1 calc R U . . .
C21 C 0.8200(8) -0.0671(3) 0.4624(3) 0.0894(18) Uani 1 1 d . . . . .
H21 H 0.837875 -0.102264 0.506535 0.107 Uiso 1 1 calc R U . . .
C22 C 0.7442(7) 0.0153(3) 0.4650(2) 0.0843(17) Uani 1 1 d . . . . .
H22 H 0.716080 0.035022 0.510612 0.101 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 Cu1 O5 92.31(9) . .
N1 Cu1 N4 170.77(11) . 1_465
O5 Cu1 N4 92.17(10) . 1_465
N1 Cu1 O1 80.29(8) . .
O5 Cu1 O1 143.80(11) . .
N4 Cu1 O1 91.35(9) 1_465 .
N1 Cu1 O7 95.30(9) . .
O5 Cu1 O7 116.65(10) . .
N4 Cu1 O7 89.90(10) 1_465 .
O1 Cu1 O7 99.37(9) . .
N2 Cu2 N3 177.41(10) . .
C5 N1 C2 106.1(2) . .
C5 N1 Cu1 139.47(19) . .
C2 N1 Cu1 114.44(17) . .
C5 N2 C3 105.6(2) . .
C5 N2 Cu2 131.53(19) . .
C3 N2 Cu2 122.72(17) . .
C17 N3 C13 117.0(2) . .
C17 N3 Cu2 116.3(2) . .
C13 N3 Cu2 126.7(2) . .
C20 N4 C21 116.1(3) . .
C20 N4 Cu1 124.3(2) . 1_645
C21 N4 Cu1 119.6(2) . 1_645
C1 O1 Cu1 113.15(18) . .
C12 O5 Cu1 131.58(19) . .
Cu1 O7 H7A 120.0 . .
Cu1 O7 H7B 113.8 . .
H7A O7 H7B 106.3 . .
O1 C1 O2 126.0(3) . .
O1 C1 C2 115.4(3) . .
O2 C1 C2 118.6(2) . .
N1 C2 C3 108.6(2) . .
N1 C2 C1 116.7(2) . .
C3 C2 C1 134.7(3) . .
C2 C3 N2 107.9(2) . .
C2 C3 C4 130.6(3) . .
N2 C3 C4 121.5(2) . .
O4 C4 O3 122.3(3) . .
O4 C4 C3 120.7(3) . .
O3 C4 C3 116.9(2) . .
N1 C5 N2 111.9(2) . .
N1 C5 C6 124.8(2) . .
N2 C5 C6 123.4(2) . .
C11 C6 C7 119.2(3) . .
C11 C6 C5 122.1(3) . .
C7 C6 C5 118.6(3) . .
C8 C7 C6 121.4(3) . .
C8 C7 H7 119.3 . .
C6 C7 H7 119.3 . .
C7 C8 C9 119.1(4) . .
C7 C8 H8 120.4 . .
C9 C8 H8 120.4 . .
C10 C9 C8 120.5(3) . .
C10 C9 H9 119.7 . .
C8 C9 H9 119.7 . .
C9 C10 C11 120.8(3) . .
C9 C10 H10 119.6 . .
C11 C10 H10 119.6 . .
C10 C11 C6 118.8(3) . .
C10 C11 C12 115.7(3) . .
C6 C11 C12 125.5(3) . .
O6 C12 O5 123.0(3) . .
O6 C12 C11 116.7(3) . .
O5 C12 C11 120.2(3) . .
N3 C13 C14 123.4(3) . .
N3 C13 H13 118.3 . .
C14 C13 H13 118.3 . .
C13 C14 C15 119.4(3) . .
C13 C14 H14 120.3 . .
C15 C14 H14 120.3 . .
C14 C15 C16 116.8(2) . .
C14 C15 C18 122.9(3) . .
C16 C15 C18 120.2(3) . .
C17 C16 C15 120.5(3) . .
C17 C16 H16 119.8 . .
C15 C16 H16 119.8 . .
N3 C17 C16 122.9(3) . .
N3 C17 H17 118.6 . .
C16 C17 H17 118.6 . .
C22 C18 C19 115.8(3) . .
C22 C18 C15 120.7(3) . .
C19 C18 C15 123.6(3) . .
C18 C19 C20 120.1(3) . .
C18 C19 H19 119.9 . .
C20 C19 H19 119.9 . .
N4 C20 C19 123.8(3) . .
N4 C20 H20 118.1 . .
C19 C20 H20 118.1 . .
N4 C21 C22 123.8(4) . .
N4 C21 H21 118.1 . .
C22 C21 H21 118.1 . .
C18 C22 C21 120.4(3) . .
C18 C22 H22 119.8 . .
C21 C22 H22 119.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 1.939(2) .
Cu1 O5 1.960(2) .
Cu1 N4 1.997(2) 1_465
Cu1 O1 2.127(2) .
Cu1 O7 2.177(2) .
Cu2 N2 1.872(2) .
Cu2 N3 1.885(2) .
N1 C5 1.338(3) .
N1 C2 1.365(3) .
N2 C5 1.351(3) .
N2 C3 1.376(3) .
N3 C17 1.337(4) .
N3 C13 1.342(4) .
N4 C20 1.312(4) .
N4 C21 1.315(5) .
O1 C1 1.256(3) .
O2 C1 1.260(4) .
O3 C4 1.306(4) .
O4 C4 1.222(3) .
O5 C12 1.266(4) .
O6 C12 1.243(4) .
O7 H7A 0.8500 .
O7 H7B 0.8499 .
C1 C2 1.472(4) .
C2 C3 1.370(3) .
C3 C4 1.475(4) .
C5 C6 1.462(4) .
C6 C11 1.401(4) .
C6 C7 1.405(4) .
C7 C8 1.371(5) .
C7 H7 0.9300 .
C8 C9 1.394(6) .
C8 H8 0.9300 .
C9 C10 1.378(5) .
C9 H9 0.9300 .
C10 C11 1.398(5) .
C10 H10 0.9300 .
C11 C12 1.515(4) .
C13 C14 1.382(4) .
C13 H13 0.9300 .
C14 C15 1.387(4) .
C14 H14 0.9300 .
C15 C16 1.387(4) .
C15 C18 1.484(4) .
C16 C17 1.372(4) .
C16 H16 0.9300 .
C17 H17 0.9300 .
C18 C22 1.367(5) .
C18 C19 1.369(4) .
C19 C20 1.381(4) .
C19 H19 0.9300 .
C20 H20 0.9300 .
C21 C22 1.374(5) .
C21 H21 0.9300 .
C22 H22 0.9300 .
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
_geom_hbond_publ_flag
O7 H7A O6 0.85 2.01 2.826(3) 162.2 1_455 yes
O7 H7B O4 0.85 2.01 2.814(3) 158.0 3_566 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
Cu1 O1 C1 O2 -177.3(3) . . . .
Cu1 O1 C1 C2 2.1(3) . . . .
C5 N1 C2 C3 0.3(3) . . . .
Cu1 N1 C2 C3 179.70(18) . . . .
C5 N1 C2 C1 -178.4(2) . . . .
Cu1 N1 C2 C1 1.0(3) . . . .
O1 C1 C2 N1 -2.1(4) . . . .
O2 C1 C2 N1 177.3(3) . . . .
O1 C1 C2 C3 179.6(3) . . . .
O2 C1 C2 C3 -1.0(5) . . . .
N1 C2 C3 N2 -0.2(3) . . . .
C1 C2 C3 N2 178.2(3) . . . .
N1 C2 C3 C4 178.1(3) . . . .
C1 C2 C3 C4 -3.5(5) . . . .
C5 N2 C3 C2 0.1(3) . . . .
Cu2 N2 C3 C2 -176.16(18) . . . .
C5 N2 C3 C4 -178.4(2) . . . .
Cu2 N2 C3 C4 5.4(4) . . . .
C2 C3 C4 O4 -179.5(3) . . . .
N2 C3 C4 O4 -1.4(4) . . . .
C2 C3 C4 O3 0.3(5) . . . .
N2 C3 C4 O3 178.4(2) . . . .
C2 N1 C5 N2 -0.3(3) . . . .
Cu1 N1 C5 N2 -179.4(2) . . . .
C2 N1 C5 C6 179.9(3) . . . .
Cu1 N1 C5 C6 0.7(5) . . . .
C3 N2 C5 N1 0.1(3) . . . .
Cu2 N2 C5 N1 175.87(19) . . . .
C3 N2 C5 C6 180.0(3) . . . .
Cu2 N2 C5 C6 -4.3(4) . . . .
N1 C5 C6 C11 42.1(4) . . . .
N2 C5 C6 C11 -137.8(3) . . . .
N1 C5 C6 C7 -141.5(3) . . . .
N2 C5 C6 C7 38.7(4) . . . .
C11 C6 C7 C8 1.2(5) . . . .
C5 C6 C7 C8 -175.3(3) . . . .
C6 C7 C8 C9 1.3(6) . . . .
C7 C8 C9 C10 -1.7(6) . . . .
C8 C9 C10 C11 -0.4(6) . . . .
C9 C10 C11 C6 2.9(5) . . . .
C9 C10 C11 C12 -179.3(3) . . . .
C7 C6 C11 C10 -3.2(5) . . . .
C5 C6 C11 C10 173.2(3) . . . .
C7 C6 C11 C12 179.2(3) . . . .
C5 C6 C11 C12 -4.4(5) . . . .
Cu1 O5 C12 O6 -125.4(3) . . . .
Cu1 O5 C12 C11 58.8(4) . . . .
C10 C11 C12 O6 -58.3(4) . . . .
C6 C11 C12 O6 119.3(3) . . . .
C10 C11 C12 O5 117.8(3) . . . .
C6 C11 C12 O5 -64.6(4) . . . .
C17 N3 C13 C14 0.1(5) . . . .
Cu2 N3 C13 C14 179.9(2) . . . .
N3 C13 C14 C15 0.4(5) . . . .
C13 C14 C15 C16 -0.5(4) . . . .
C13 C14 C15 C18 179.8(3) . . . .
C14 C15 C16 C17 0.1(5) . . . .
C18 C15 C16 C17 179.9(3) . . . .
C13 N3 C17 C16 -0.5(5) . . . .
Cu2 N3 C17 C16 179.7(3) . . . .
C15 C16 C17 N3 0.3(5) . . . .
C14 C15 C18 C22 167.9(4) . . . .
C16 C15 C18 C22 -11.9(5) . . . .
C14 C15 C18 C19 -11.2(5) . . . .
C16 C15 C18 C19 169.1(3) . . . .
C22 C18 C19 C20 -0.5(6) . . . .
C15 C18 C19 C20 178.6(4) . . . .
C21 N4 C20 C19 0.8(7) . . . .
Cu1 N4 C20 C19 -179.4(3) 1_645 . . .
C18 C19 C20 N4 0.5(7) . . . .
C20 N4 C21 C22 -2.2(8) . . . .
Cu1 N4 C21 C22 178.1(5) 1_645 . . .
C19 C18 C22 C21 -0.7(7) . . . .
C15 C18 C22 C21 -179.8(5) . . . .
N4 C21 C22 C18 2.2(9) . . . .
