#------------------------------------------------------------------------------
#$Date: 2021-02-20 08:15:57 +0200 (Sat, 20 Feb 2021) $
#$Revision: 262111 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/37/2243753.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_2243753
loop_
_publ_author_name
'Gao, Sen'
'Fronczek, Frank R.'
'Maverick, Andrew W.'
_publ_section_title
;
 A copper complex of an unusual hydroxy--carboxylate ligand:
 [Cu(bpy)(C₄H₄O₆)]
;
_journal_coeditor_code           PK2655
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              282
_journal_page_last               285
_journal_paper_doi               10.1107/S2056989021001286
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          '[Cu (C4 H4 O6) (C10 H8 N2)]'
_chemical_formula_moiety         'C10 H8 N2, Cu, C4 H4 O6'
_chemical_formula_sum            'C14 H12 Cu N2 O6'
_chemical_formula_weight         367.80
_chemical_name_common            (bpy)Cu(2-(hydroxymethyl)tartronate)
_chemical_name_systematic
'[(2,2'-Bipyridine-κ²N,N')[2-hydroxy-2-(hydroxymethyl-κO)propanedioato-κ²O¹,O³]copper(II)]'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                95.204(4)
_cell_angle_beta                 107.729(4)
_cell_angle_gamma                111.462(4)
_cell_formula_units_Z            2
_cell_length_a                   7.6516(5)
_cell_length_b                   9.9272(6)
_cell_length_c                   10.0722(6)
_cell_measurement_reflns_used    3354
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      29.26
_cell_measurement_theta_min      2.18
_cell_volume                     660.34(8)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014/7 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEXII DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0827
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18442
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.564
_diffrn_reflns_theta_min         2.180
_exptl_absorpt_coefficient_mu    1.691
_exptl_absorpt_correction_T_max  0.891
_exptl_absorpt_correction_T_min  0.838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            'light blue'
_exptl_crystal_density_diffrn    1.850
_exptl_crystal_description       fragment
_exptl_crystal_F_000             374
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.735
_refine_diff_density_min         -0.559
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         4041
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0489
_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)+(0.0436P)²+0.3982P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.1049
_reflns_number_gt                2675
_reflns_number_total             4041
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            pk2655sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        660.34(7)
_cod_database_code               2243753
_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   0.786
_shelx_estimated_absorpt_t_max   0.891
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.60628(6) 0.63056(4) 0.41304(4) 0.01841(12) Uani d 1 . .
O O1 0.7261(3) 0.5158(2) 0.52799(19) 0.0200(5) Uani d 1 . .
O O2 0.9188(3) 0.7153(3) 0.3763(2) 0.0247(5) Uani d 1 . .
H H2O 0.931(6) 0.635(3) 0.346(4) 0.037 Uiso d 1 . .
O O3 0.7221(3) 0.7944(2) 0.5778(2) 0.0241(5) Uani d 1 . .
O O4 0.9916(3) 0.5149(2) 0.6990(2) 0.0239(5) Uani d 1 . .
O O5 1.2089(3) 0.8062(3) 0.7594(2) 0.0296(5) Uani d 1 . .
H H5O 1.178(6) 0.869(4) 0.813(3) 0.044 Uiso d 1 . .
O O6 0.9741(4) 0.9263(3) 0.7840(2) 0.0337(6) Uani d 1 . .
N N1 0.4537(4) 0.7282(3) 0.2933(2) 0.0170(5) Uani d 1 . .
N N2 0.4699(4) 0.4750(3) 0.2317(2) 0.0166(5) Uani d 1 . .
C C1 0.4522(5) 0.8585(3) 0.3373(3) 0.0201(6) Uani d 1 . .
H H1 0.5308 0.9116 0.4337 0.024 Uiso calc 1 . .
C C2 0.3410(5) 0.9188(3) 0.2483(3) 0.0217(7) Uani d 1 . .
H H2 0.3409 1.0109 0.2833 0.026 Uiso calc 1 . .
C C3 0.2293(4) 0.8435(3) 0.1071(3) 0.0195(6) Uani d 1 . .
H H3 0.1527 0.8836 0.0433 0.023 Uiso calc 1 . .
C C4 0.2309(4) 0.7080(3) 0.0597(3) 0.0180(6) Uani d 1 . .
H H4 0.1567 0.6548 -0.0372 0.022 Uiso calc 1 . .
C C5 0.3422(4) 0.6519(3) 0.1558(3) 0.0142(6) Uani d 1 . .
C C6 0.3512(4) 0.5078(3) 0.1208(3) 0.0142(6) Uani d 1 . .
C C7 0.2500(4) 0.4119(3) -0.0127(3) 0.0155(6) Uani d 1 . .
H H7 0.1676 0.4365 -0.0892 0.019 Uiso calc 1 . .
C C8 0.2703(4) 0.2792(3) -0.0335(3) 0.0180(6) Uani d 1 . .
H H8 0.2000 0.2107 -0.1239 0.022 Uiso calc 1 . .
C C9 0.3938(5) 0.2480(3) 0.0789(3) 0.0191(6) Uani d 1 . .
H H9 0.4109 0.1583 0.0665 0.023 Uiso calc 1 . .
C C10 0.4924(4) 0.3482(3) 0.2098(3) 0.0180(6) Uani d 1 . .
H H10 0.5788 0.3267 0.2866 0.022 Uiso calc 1 . .
C C11 0.9051(5) 0.5800(3) 0.6238(3) 0.0217(7) Uani d 1 . .
C C12 1.0222(5) 0.7493(4) 0.6426(3) 0.0247(7) Uani d 1 . .
C C13 0.8962(5) 0.8297(4) 0.6718(3) 0.0258(7) Uani d 1 . .
C C14 1.0784(5) 0.7878(4) 0.5103(3) 0.0284(7) Uani d 1 . .
H H14A 1.1263 0.8965 0.5195 0.034 Uiso calc 1 . .
H H14B 1.1917 0.7614 0.5117 0.034 Uiso calc 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
O3 Cu1 O1 . . 91.06(8) ?
O3 Cu1 N1 . . 91.97(9) ?
O1 Cu1 N1 . . 173.29(10) ?
O3 Cu1 N2 . . 173.32(9) ?
O1 Cu1 N2 . . 95.56(9) ?
N1 Cu1 N2 . . 81.35(9) ?
O3 Cu1 O2 . . 90.05(9) ?
O1 Cu1 O2 . . 81.94(8) ?
N1 Cu1 O2 . . 104.04(9) ?
N2 Cu1 O2 . . 91.77(9) ?
C11 O1 Cu1 . . 120.61(19) ?
C14 O2 Cu1 . . 108.93(18) ?
C14 O2 H2O . . 106(2) ?
Cu1 O2 H2O . . 106(2) ?
C13 O3 Cu1 . . 121.7(2) ?
C12 O5 H5O . . 96(2) ?
C1 N1 C5 . . 119.1(2) ?
C1 N1 Cu1 . . 125.71(19) ?
C5 N1 Cu1 . . 115.18(19) ?
C10 N2 C6 . . 119.0(2) ?
C10 N2 Cu1 . . 126.08(19) ?
C6 N2 Cu1 . . 114.81(18) ?
N1 C1 C2 . . 122.5(3) ?
N1 C1 H1 . . 118.8 ?
C2 C1 H1 . . 118.8 ?
C1 C2 C3 . . 119.0(3) ?
C1 C2 H2 . . 120.5 ?
C3 C2 H2 . . 120.5 ?
C2 C3 C4 . . 119.0(3) ?
C2 C3 H3 . . 120.5 ?
C4 C3 H3 . . 120.5 ?
C5 C4 C3 . . 119.0(3) ?
C5 C4 H4 . . 120.5 ?
C3 C4 H4 . . 120.5 ?
N1 C5 C4 . . 121.4(3) ?
N1 C5 C6 . . 114.2(2) ?
C4 C5 C6 . . 124.4(2) ?
N2 C6 C7 . . 121.5(3) ?
N2 C6 C5 . . 114.4(2) ?
C7 C6 C5 . . 124.1(2) ?
C6 C7 C8 . . 119.1(3) ?
C6 C7 H7 . . 120.4 ?
C8 C7 H7 . . 120.4 ?
C9 C8 C7 . . 119.0(3) ?
C9 C8 H8 . . 120.5 ?
C7 C8 H8 . . 120.5 ?
C8 C9 C10 . . 119.5(3) ?
C8 C9 H9 . . 120.3 ?
C10 C9 H9 . . 120.3 ?
N2 C10 C9 . . 121.9(3) ?
N2 C10 H10 . . 119.1 ?
C9 C10 H10 . . 119.1 ?
O4 C11 O1 . . 124.3(3) ?
O4 C11 C12 . . 117.9(3) ?
O1 C11 C12 . . 117.8(2) ?
O5 C12 C13 . . 108.3(2) ?
O5 C12 C11 . . 111.3(2) ?
C13 C12 C11 . . 109.2(3) ?
O5 C12 C14 . . 105.0(3) ?
C13 C12 C14 . . 110.5(3) ?
C11 C12 C14 . . 112.4(2) ?
O6 C13 O3 . . 125.2(3) ?
O6 C13 C12 . . 117.0(3) ?
O3 C13 C12 . . 117.8(3) ?
O2 C14 C12 . . 114.7(3) ?
O2 C14 H14A . . 108.6 ?
C12 C14 H14A . . 108.6 ?
O2 C14 H14B . . 108.6 ?
C12 C14 H14B . . 108.6 ?
H14A C14 H14B . . 107.6 ?
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 O3 . 1.935(2) ?
Cu1 O1 . 1.9587(19) ?
Cu1 N1 . 1.985(2) ?
Cu1 N2 . 1.990(2) ?
Cu1 O2 . 2.384(2) ?
O1 C11 . 1.288(3) ?
O2 C14 . 1.417(4) ?
O2 H2O . 0.880(18) ?
O3 C13 . 1.275(4) ?
O4 C11 . 1.236(3) ?
O5 C12 . 1.417(4) ?
O5 H5O . 0.929(18) ?
O6 C13 . 1.236(4) ?
N1 C1 . 1.334(4) ?
N1 C5 . 1.355(3) ?
N2 C10 . 1.339(4) ?
N2 C6 . 1.358(3) ?
C1 C2 . 1.375(4) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.383(4) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.391(4) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.383(4) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.474(4) ?
C6 C7 . 1.381(4) ?
C7 C8 . 1.387(4) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.377(4) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.380(4) ?
C9 H9 . 0.9500 ?
C10 H10 . 0.9500 ?
C11 C12 . 1.549(5) ?
C12 C13 . 1.532(4) ?
C12 C14 . 1.558(4) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
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
O2 H2O O4 2_766 0.880(18) 1.85(2) 2.723(3) 169(4)
O5 H5O O6 . 0.929(18) 1.80(3) 2.549(3) 136(3)
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
C5 N1 C1 C2 . . . . 0.1(5) ?
Cu1 N1 C1 C2 . . . . -179.4(2) ?
N1 C1 C2 C3 . . . . -1.3(5) ?
C1 C2 C3 C4 . . . . 0.8(5) ?
C2 C3 C4 C5 . . . . 0.8(4) ?
C1 N1 C5 C4 . . . . 1.5(4) ?
Cu1 N1 C5 C4 . . . . -178.9(2) ?
C1 N1 C5 C6 . . . . -178.4(3) ?
Cu1 N1 C5 C6 . . . . 1.2(3) ?
C3 C4 C5 N1 . . . . -2.0(4) ?
C3 C4 C5 C6 . . . . 177.9(3) ?
C10 N2 C6 C7 . . . . 1.6(4) ?
Cu1 N2 C6 C7 . . . . 178.7(2) ?
C10 N2 C6 C5 . . . . -178.2(3) ?
Cu1 N2 C6 C5 . . . . -1.1(3) ?
N1 C5 C6 N2 . . . . -0.1(4) ?
C4 C5 C6 N2 . . . . -179.9(3) ?
N1 C5 C6 C7 . . . . -179.9(3) ?
C4 C5 C6 C7 . . . . 0.3(5) ?
N2 C6 C7 C8 . . . . 0.0(4) ?
C5 C6 C7 C8 . . . . 179.8(3) ?
C6 C7 C8 C9 . . . . -1.2(4) ?
C7 C8 C9 C10 . . . . 0.8(4) ?
C6 N2 C10 C9 . . . . -2.0(4) ?
Cu1 N2 C10 C9 . . . . -178.8(2) ?
C8 C9 C10 N2 . . . . 0.8(5) ?
Cu1 O1 C11 O4 . . . . -179.0(2) ?
Cu1 O1 C11 C12 . . . . -1.0(4) ?
O4 C11 C12 O5 . . . . -6.9(4) ?
O1 C11 C12 O5 . . . . 175.0(2) ?
O4 C11 C12 C13 . . . . -126.3(3) ?
O1 C11 C12 C13 . . . . 55.6(3) ?
O4 C11 C12 C14 . . . . 110.7(3) ?
O1 C11 C12 C14 . . . . -67.4(4) ?
Cu1 O3 C13 O6 . . . . -175.1(3) ?
Cu1 O3 C13 C12 . . . . 6.5(4) ?
O5 C12 C13 O6 . . . . 1.0(4) ?
C11 C12 C13 O6 . . . . 122.3(3) ?
C14 C12 C13 O6 . . . . -113.5(3) ?
O5 C12 C13 O3 . . . . 179.6(3) ?
C11 C12 C13 O3 . . . . -59.1(4) ?
C14 C12 C13 O3 . . . . 65.1(4) ?
Cu1 O2 C14 C12 . . . . 19.3(3) ?
O5 C12 C14 O2 . . . . 167.8(3) ?
C13 C12 C14 O2 . . . . -75.7(3) ?
C11 C12 C14 O2 . . . . 46.6(4) ?

_cod_database_fobs_code 2243753
