##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_1
_audit_creation_method     'SHELXL-2018/3'
_database_code_depnum_ccdc_archive     'CCDC 1901534'
_chemical_name_systematic
;\
(Benzoato-κ²O,O')[(E)-2-({[2-(diethylamino)ethyl]\
imino}methyl)phenolato-κ³N,N',O]copper(II) dihydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H24 Cu N2 O3, 2(H2 O)'
_chemical_formula_sum     'C20 H28 Cu N2 O5'
_chemical_formula_iupac     '[Cu (C7 H5 O2) (C13 H19 N2 O)], 2H2 O1'
_chemical_formula_weight     439.98
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/c'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     11.2427(3)
_cell_length_b     10.1287(2)
_cell_length_c     17.7683(3)
_cell_angle_alpha     90
_cell_angle_beta     92.501(2)
_cell_angle_gamma     90
_cell_volume     2021.42(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     20474
_cell_measurement_theta_min     3.7550
_cell_measurement_theta_max     40.9290
_cell_measurement_temperature     100(2)
_exptl_crystal_description
;
multi-faceted prism
;
_exptl_crystal_colour     blue
_exptl_crystal_size_max     0.350
_exptl_crystal_size_mid     0.232
_exptl_crystal_size_min     0.182
_exptl_crystal_density_diffrn     1.446
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     924
_exptl_absorpt_coefficient_mu     1.114
_exptl_absorpt_correction_type     gaussian
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2018)
;
_exptl_absorpt_correction_T_min     0.474
_exptl_absorpt_correction_T_max     1.000
_diffrn_ambient_temperature     100(2)
_diffrn_source     'micro-focus sealed X-ray tube'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type
         'Rigaku OD SuperNova Dual source diffractometer with an Atlas detector'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     10.6501
_diffrn_reflns_number     51132
_diffrn_reflns_av_R_equivalents     0.0298
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_theta_min     3.499
_diffrn_reflns_theta_max     41.261
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.972
_diffrn_measured_fraction_theta_full     0.987
_diffrn_reflns_limit_h_min     -20
_diffrn_reflns_limit_h_max     20
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -25
_diffrn_reflns_limit_l_max     32
_refine_special_details     ?
_reflns_number_total     13125
_reflns_number_gt     10770
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0415
_refine_ls_R_factor_gt     0.0283
_refine_ls_wR_factor_gt     0.0694
_refine_ls_wR_factor_ref     0.0756
_refine_ls_goodness_of_fit_ref     1.066
_refine_ls_restrained_S_all     1.066
_refine_ls_number_reflns     13125
_refine_ls_number_parameters     270
_refine_ls_number_restraints     6
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0327P)²+0.3747P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.566
_refine_diff_density_min     -0.602
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
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 Cu 0.23818(2) 0.69525(2) 0.47778(2) 0.01137(2) Uani d 1 . .
    O O1 0.27766(5) 0.54601(5) 0.41727(3) 0.01650(9) Uani d 1 . .
    O O2 0.15402(5) 0.78344(6) 0.39331(3) 0.01670(9) Uani d 1 . .
    O O3 0.33453(5) 0.86472(6) 0.37715(3) 0.01897(10) Uani d 1 . .
    O O1W 0.52308(7) 0.83109(7) 0.28425(4) 0.02636(13) Uani d 1 . .
    H H1W1 0.4716(12) 0.8598(15) 0.3113(8) 0.034(4) Uiso d 1 . .
    H H1W2 0.5502(16) 0.8967(16) 0.2641(10) 0.060(5) Uiso d 1 . .
    O O2W 0.39643(9) 0.57738(7) 0.27758(4) 0.03167(16) Uani d 1 . .
    H H2W1 0.3575(13) 0.5822(15) 0.3162(8) 0.037(4) Uiso d 1 . .
    H H2W2 0.4310(14) 0.6492(14) 0.2765(9) 0.042(4) Uiso d 1 . .
    N N1 0.33000(6) 0.63419(6) 0.56489(3) 0.01338(9) Uani d 1 . .
    N N2 0.16538(6) 0.82506(6) 0.55446(3) 0.01380(9) Uani d 1 . .
    C C1 0.32672(6) 0.43555(7) 0.44259(4) 0.01414(10) Uani d 1 . .
    C C2 0.32873(8) 0.32474(8) 0.39411(5) 0.02019(13) Uani d 1 . .
    H H2A 0.294165 0.331522 0.344513 0.024 Uiso calc 1 . .
    C C3 0.38021(8) 0.20647(8) 0.41763(6) 0.02339(15) Uani d 1 . .
    H H3A 0.378582 0.133178 0.384235 0.028 Uiso calc 1 . .
    C C4 0.43441(8) 0.19302(7) 0.48948(6) 0.02259(15) Uani d 1 . .
    H H4A 0.471294 0.112327 0.504607 0.027 Uiso calc 1 . .
    C C5 0.43329(8) 0.29896(7) 0.53786(5) 0.01865(12) Uani d 1 . .
    H H5A 0.469865 0.290767 0.586855 0.022 Uiso calc 1 . .
    C C6 0.37906(6) 0.41938(7) 0.51635(4) 0.01382(10) Uani d 1 . .
    C C7 0.38029(6) 0.52083(7) 0.57282(4) 0.01411(10) Uani d 1 . .
    H H7A 0.421362 0.502782 0.619548 0.017 Uiso calc 1 . .
    C C8 0.32821(7) 0.72459(8) 0.62904(4) 0.01648(11) Uani d 1 . .
    H H8A 0.383817 0.799046 0.622365 0.020 Uiso calc 1 . .
    H H8B 0.351197 0.678039 0.676465 0.020 Uiso calc 1 . .
    C C9 0.20140(7) 0.77360(8) 0.63053(4) 0.01702(12) Uani d 1 . .
    H H9A 0.147997 0.700558 0.644253 0.020 Uiso calc 1 . .
    H H9B 0.195502 0.844521 0.668525 0.020 Uiso calc 1 . .
    C C10 0.21916(7) 0.95742(7) 0.54046(4) 0.01689(12) Uani d 1 . .
    H H10A 0.188508 0.989212 0.490618 0.020 Uiso calc 1 . .
    H H10B 0.306310 0.946107 0.537607 0.020 Uiso calc 1 . .
    C C11 0.19639(9) 1.06407(8) 0.59850(5) 0.02305(15) Uani d 1 . .
    H H11A 0.226691 1.148804 0.580836 0.035 Uiso calc 1 . .
    H H11B 0.237177 1.040824 0.646542 0.035 Uiso calc 1 . .
    H H11C 0.110635 1.071227 0.605459 0.035 Uiso calc 1 . .
    C C12 0.03368(7) 0.82973(8) 0.54397(5) 0.01943(13) Uani d 1 . .
    H H12A 0.012276 0.883028 0.498678 0.023 Uiso calc 1 . .
    H H12B 0.000355 0.874369 0.587918 0.023 Uiso calc 1 . .
    C C13 -0.02251(8) 0.69370(9) 0.53516(6) 0.02444(15) Uani d 1 . .
    H H13A -0.109103 0.702796 0.528447 0.037 Uiso calc 1 . .
    H H13B 0.008651 0.649662 0.491031 0.037 Uiso calc 1 . .
    H H13C -0.003276 0.640999 0.580316 0.037 Uiso calc 1 . .
    C C14 0.22685(7) 0.85663(7) 0.35854(4) 0.01419(10) Uani d 1 . .
    C C15 0.17491(7) 0.93920(7) 0.29497(4) 0.01484(11) Uani d 1 . .
    C C16 0.24644(8) 1.02998(8) 0.25883(4) 0.01974(13) Uani d 1 . .
    H H16A 0.328766 1.035916 0.272873 0.024 Uiso calc 1 . .
    C C17 0.19839(10) 1.11179(9) 0.20249(5) 0.02590(17) Uani d 1 . .
    H H17A 0.247678 1.173462 0.178319 0.031 Uiso calc 1 . .
    C C18 0.07821(10) 1.10309(9) 0.18165(5) 0.02722(18) Uani d 1 . .
    H H18A 0.045041 1.159443 0.143495 0.033 Uiso calc 1 . .
    C C19 0.00625(9) 1.01191(10) 0.21660(5) 0.02489(16) Uani d 1 . .
    H H19A -0.075915 1.005821 0.202140 0.030 Uiso calc 1 . .
    C C20 0.05468(8) 0.92951(8) 0.27283(4) 0.01896(12) Uani d 1 . .
    H H20A 0.005618 0.866548 0.296135 0.023 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    Cu O1 . 1.9183(5) ?
    Cu N1 . 1.9246(6) ?
    Cu O2 . 1.9550(6) ?
    Cu N2 . 2.0863(6) ?
    Cu O3 . 2.7360(6) ?
    O1 C1 . 1.3178(9) ?
    O2 C14 . 1.2828(9) ?
    O3 C14 . 1.2437(10) ?
    O1W H1W1 . 0.821(12) ?
    O1W H1W2 . 0.820(14) ?
    O2W H2W1 . 0.831(12) ?
    O2W H2W2 . 0.825(13) ?
    N1 C7 . 1.2849(9) ?
    N1 C8 . 1.4630(9) ?
    N2 C12 . 1.4850(10) ?
    N2 C9 . 1.4881(10) ?
    N2 C10 . 1.4960(9) ?
    C1 C2 . 1.4156(10) ?
    C1 C6 . 1.4225(10) ?
    C2 C3 . 1.3870(12) ?
    C2 H2A . 0.9500 ?
    C3 C4 . 1.3970(15) ?
    C3 H3A . 0.9500 ?
    C4 C5 . 1.3754(12) ?
    C4 H4A . 0.9500 ?
    C5 C6 . 1.4089(10) ?
    C5 H5A . 0.9500 ?
    C6 C7 . 1.4359(10) ?
    C7 H7A . 0.9500 ?
    C8 C9 . 1.5110(11) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 C11 . 1.5228(11) ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
    C12 C13 . 1.5210(12) ?
    C12 H12A . 0.9900 ?
    C12 H12B . 0.9900 ?
    C13 H13A . 0.9800 ?
    C13 H13B . 0.9800 ?
    C13 H13C . 0.9800 ?
    C14 C15 . 1.5029(9) ?
    C15 C20 . 1.3947(11) ?
    C15 C16 . 1.3963(11) ?
    C16 C17 . 1.3904(12) ?
    C16 H16A . 0.9500 ?
    C17 C18 . 1.3881(16) ?
    C17 H17A . 0.9500 ?
    C18 C19 . 1.3917(15) ?
    C18 H18A . 0.9500 ?
    C19 C20 . 1.3941(11) ?
    C19 H19A . 0.9500 ?
    C20 H20A . 0.9500 ?
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 Cu N1 . . 93.92(2) ?
    O1 Cu O2 . . 92.62(2) ?
    N1 Cu O2 . . 171.44(3) ?
    O1 Cu N2 . . 165.85(2) ?
    N1 Cu N2 . . 83.64(2) ?
    O2 Cu N2 . . 91.31(2) ?
    O1 Cu O3 . . 91.16(2) ?
    N1 Cu O3 . . 120.89(2) ?
    O2 Cu O3 . . 53.40(2) ?
    N2 Cu O3 . . 102.08(2) ?
    C1 O1 Cu . . 125.54(5) ?
    C14 O2 Cu . . 109.64(5) ?
    C14 O3 Cu . . 73.97(4) ?
    H1W1 O1W H1W2 . . 104.6(15) ?
    H2W1 O2W H2W2 . . 103.5(14) ?
    C7 N1 C8 . . 119.66(6) ?
    C7 N1 Cu . . 126.40(5) ?
    C8 N1 Cu . . 113.60(5) ?
    C12 N2 C9 . . 110.82(6) ?
    C12 N2 C10 . . 111.01(6) ?
    C9 N2 C10 . . 111.65(6) ?
    C12 N2 Cu . . 110.82(5) ?
    C9 N2 Cu . . 105.87(4) ?
    C10 N2 Cu . . 106.45(4) ?
    O1 C1 C2 . . 118.88(7) ?
    O1 C1 C6 . . 124.23(6) ?
    C2 C1 C6 . . 116.89(7) ?
    C3 C2 C1 . . 121.27(8) ?
    C3 C2 H2A . . 119.4 ?
    C1 C2 H2A . . 119.4 ?
    C2 C3 C4 . . 121.28(7) ?
    C2 C3 H3A . . 119.4 ?
    C4 C3 H3A . . 119.4 ?
    C5 C4 C3 . . 118.66(8) ?
    C5 C4 H4A . . 120.7 ?
    C3 C4 H4A . . 120.7 ?
    C4 C5 C6 . . 121.43(8) ?
    C4 C5 H5A . . 119.3 ?
    C6 C5 H5A . . 119.3 ?
    C5 C6 C1 . . 120.43(7) ?
    C5 C6 C7 . . 116.04(7) ?
    C1 C6 C7 . . 123.53(6) ?
    N1 C7 C6 . . 124.89(6) ?
    N1 C7 H7A . . 117.6 ?
    C6 C7 H7A . . 117.6 ?
    N1 C8 C9 . . 105.33(6) ?
    N1 C8 H8A . . 110.7 ?
    C9 C8 H8A . . 110.7 ?
    N1 C8 H8B . . 110.7 ?
    C9 C8 H8B . . 110.7 ?
    H8A C8 H8B . . 108.8 ?
    N2 C9 C8 . . 108.59(6) ?
    N2 C9 H9A . . 110.0 ?
    C8 C9 H9A . . 110.0 ?
    N2 C9 H9B . . 110.0 ?
    C8 C9 H9B . . 110.0 ?
    H9A C9 H9B . . 108.4 ?
    N2 C10 C11 . . 116.23(6) ?
    N2 C10 H10A . . 108.2 ?
    C11 C10 H10A . . 108.2 ?
    N2 C10 H10B . . 108.2 ?
    C11 C10 H10B . . 108.2 ?
    H10A C10 H10B . . 107.4 ?
    C10 C11 H11A . . 109.5 ?
    C10 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C10 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    N2 C12 C13 . . 113.04(7) ?
    N2 C12 H12A . . 109.0 ?
    C13 C12 H12A . . 109.0 ?
    N2 C12 H12B . . 109.0 ?
    C13 C12 H12B . . 109.0 ?
    H12A C12 H12B . . 107.8 ?
    C12 C13 H13A . . 109.5 ?
    C12 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    C12 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    O3 C14 O2 . . 122.98(6) ?
    O3 C14 C15 . . 120.33(7) ?
    O2 C14 C15 . . 116.63(7) ?
    C20 C15 C16 . . 119.15(7) ?
    C20 C15 C14 . . 120.86(7) ?
    C16 C15 C14 . . 119.96(7) ?
    C17 C16 C15 . . 120.67(9) ?
    C17 C16 H16A . . 119.7 ?
    C15 C16 H16A . . 119.7 ?
    C18 C17 C16 . . 119.82(9) ?
    C18 C17 H17A . . 120.1 ?
    C16 C17 H17A . . 120.1 ?
    C17 C18 C19 . . 120.08(8) ?
    C17 C18 H18A . . 120.0 ?
    C19 C18 H18A . . 120.0 ?
    C18 C19 C20 . . 120.04(9) ?
    C18 C19 H19A . . 120.0 ?
    C20 C19 H19A . . 120.0 ?
    C19 C20 C15 . . 120.23(8) ?
    C19 C20 H20A . . 119.9 ?
    C15 C20 H20A . . 119.9 ?
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
    Cu O1 C1 C2 . . . . 167.40(5) ?
    Cu O1 C1 C6 . . . . -12.80(10) ?
    O1 C1 C2 C3 . . . . 179.39(8) ?
    C6 C1 C2 C3 . . . . -0.42(11) ?
    C1 C2 C3 C4 . . . . -1.45(13) ?
    C2 C3 C4 C5 . . . . 1.69(13) ?
    C3 C4 C5 C6 . . . . -0.04(12) ?
    C4 C5 C6 C1 . . . . -1.84(11) ?
    C4 C5 C6 C7 . . . . 177.93(7) ?
    O1 C1 C6 C5 . . . . -177.78(7) ?
    C2 C1 C6 C5 . . . . 2.02(10) ?
    O1 C1 C6 C7 . . . . 2.47(11) ?
    C2 C1 C6 C7 . . . . -177.73(7) ?
    C8 N1 C7 C6 . . . . 174.37(7) ?
    Cu N1 C7 C6 . . . . 1.60(11) ?
    C5 C6 C7 N1 . . . . -176.20(7) ?
    C1 C6 C7 N1 . . . . 3.56(11) ?
    C7 N1 C8 C9 . . . . -133.03(7) ?
    Cu N1 C8 C9 . . . . 40.63(7) ?
    C12 N2 C9 C8 . . . . 159.78(6) ?
    C10 N2 C9 C8 . . . . -75.90(7) ?
    Cu N2 C9 C8 . . . . 39.55(7) ?
    N1 C8 C9 N2 . . . . -52.20(8) ?
    C12 N2 C10 C11 . . . . 69.58(9) ?
    C9 N2 C10 C11 . . . . -54.64(9) ?
    Cu N2 C10 C11 . . . . -169.73(6) ?
    C9 N2 C12 C13 . . . . -71.87(8) ?
    C10 N2 C12 C13 . . . . 163.45(7) ?
    Cu N2 C12 C13 . . . . 45.36(8) ?
    Cu O3 C14 O2 . . . . -0.92(6) ?
    Cu O3 C14 C15 . . . . 176.22(6) ?
    Cu O2 C14 O3 . . . . 1.32(9) ?
    Cu O2 C14 C15 . . . . -175.93(5) ?
    O3 C14 C15 C20 . . . . 179.00(7) ?
    O2 C14 C15 C20 . . . . -3.67(10) ?
    O3 C14 C15 C16 . . . . -3.00(10) ?
    O2 C14 C15 C16 . . . . 174.33(7) ?
    C20 C15 C16 C17 . . . . 1.29(11) ?
    C14 C15 C16 C17 . . . . -176.75(7) ?
    C15 C16 C17 C18 . . . . -0.21(13) ?
    C16 C17 C18 C19 . . . . -0.57(13) ?
    C17 C18 C19 C20 . . . . 0.26(13) ?
    C18 C19 C20 C15 . . . . 0.83(12) ?
    C16 C15 C20 C19 . . . . -1.60(11) ?
    C14 C15 C20 C19 . . . . 176.42(7) ?
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
    _geom_hbond_publ_flag
    O1W H1W1 O3 . 0.821(12) 1.976(12) 2.7641(9) 160.6(15) yes
    O1W H1W2 O2W 2_655 0.820(14) 2.073(14) 2.8871(10) 172.2(18) yes
    O2W H2W1 O1 . 0.831(12) 2.075(12) 2.8868(9) 165.3(15) yes
    O2W H2W2 O1W . 0.825(13) 2.115(13) 2.9378(11) 174.9(17) yes
_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     ?
_shelx_estimated_absorpt_T_max     ?
data_2
_audit_creation_method     'SHELXL-2018/3'
_database_code_depnum_ccdc_archive     'CCDC 1901535'
_chemical_name_systematic
;\
[(E)-2-({[2-(Diethylamino)ethyl]imino}methyl)phenolato-\
κ³N,N',O](2-phenylacetato-κ²O,O')\
copper(II)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H26 Cu N2 O3'
_chemical_formula_sum     'C21 H26 Cu N2 O3'
_chemical_formula_iupac     '[Cu (C8 H7 O2) (C13 H19 N2 O)]'
_chemical_formula_weight     417.98
_chemical_melting_point     ?
_chemical_absolute_configuration     ad
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P c a 21'
_space_group_name_Hall     'P 2c -2ac'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    'x+1/2, -y, z'
    '-x+1/2, y, z+1/2'
_cell_length_a     23.1862(10)
_cell_length_b     6.4178(3)
_cell_length_c     13.1598(6)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1958.22(15)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6436
_cell_measurement_theta_min     3.9290
_cell_measurement_theta_max     33.5560
_cell_measurement_temperature     100(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     blue
_exptl_crystal_size_max     0.198
_exptl_crystal_size_mid     0.106
_exptl_crystal_size_min     0.028
_exptl_crystal_density_diffrn     1.418
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     876
_exptl_absorpt_coefficient_mu     1.139
_exptl_absorpt_correction_type     gaussian
_exptl_absorpt_process_details
;
CrysAlis PRO (Rigaku OD, 2018)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model. Empirical absorption correction
using spherical harmonics, implemented in SCALE3 ABSPACK scaling
algorithm.
;
_exptl_absorpt_correction_T_min     0.684
_exptl_absorpt_correction_T_max     1.000
_diffrn_ambient_temperature     100(2)
_diffrn_source     'micro-focus sealed X-ray tube'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type
         'Rigaku OD SuperNova Dual source diffractometer with an Atlas detector'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     10.6501
_diffrn_reflns_number     46196
_diffrn_reflns_av_R_equivalents     0.0890
_diffrn_reflns_av_unetI/netI     0.0950
_diffrn_reflns_theta_min     3.515
_diffrn_reflns_theta_max     41.261
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.978
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -37
_diffrn_reflns_limit_h_max     42
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     22
_refine_special_details     ?
_reflns_number_total     11501
_reflns_number_gt     7093
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1145
_refine_ls_R_factor_gt     0.0557
_refine_ls_wR_factor_gt     0.0951
_refine_ls_wR_factor_ref     0.1207
_refine_ls_goodness_of_fit_ref     1.040
_refine_ls_restrained_S_all     1.040
_refine_ls_number_reflns     11501
_refine_ls_number_parameters     245
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0359P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     1.198
_refine_diff_density_min     -1.038
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack x determined using 1976 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack     -0.035(10)
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'
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
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 Cu 0.50251(2) 0.67151(4) 0.58234(5) 0.01478(6) Uani d 1 . .
    O O1 0.55832(9) 0.8376(3) 0.51299(18) 0.0204(4) Uani d 1 . .
    O O2 0.44362(8) 0.8849(3) 0.55955(16) 0.0185(4) Uani d 1 . .
    O O3 0.43374(10) 0.6755(3) 0.42593(18) 0.0219(5) Uani d 1 . .
    N N1 0.55334(9) 0.4358(3) 0.5937(2) 0.0180(5) Uani d 1 . .
    N N2 0.45221(10) 0.5167(4) 0.68793(19) 0.0176(4) Uani d 1 . .
    C C1 0.61121(12) 0.7875(4) 0.4914(2) 0.0167(5) Uani d 1 . .
    C C2 0.64665(13) 0.9369(5) 0.4416(2) 0.0186(5) Uani d 1 . .
    H H2A 0.630815 1.069146 0.425069 0.022 Uiso calc 1 . .
    C C3 0.70285(13) 0.8961(5) 0.4169(2) 0.0201(5) Uani d 1 . .
    H H3A 0.725123 1.000151 0.383750 0.024 Uiso calc 1 . .
    C C4 0.72806(13) 0.7032(5) 0.4396(2) 0.0215(6) Uani d 1 . .
    H H4A 0.767133 0.675768 0.422466 0.026 Uiso calc 1 . .
    C C5 0.69497(12) 0.5539(5) 0.4874(2) 0.0200(5) Uani d 1 . .
    H H5A 0.711564 0.422133 0.502459 0.024 Uiso calc 1 . .
    C C6 0.63715(12) 0.5921(5) 0.5145(2) 0.0176(5) Uani d 1 . .
    C C7 0.60647(11) 0.4276(4) 0.5657(2) 0.0181(6) Uani d 1 . .
    H H7A 0.627107 0.303159 0.580009 0.022 Uiso calc 1 . .
    C C8 0.52631(13) 0.2571(5) 0.6443(3) 0.0224(6) Uani d 1 . .
    H H8A 0.556181 0.164060 0.673164 0.027 Uiso calc 1 . .
    H H8B 0.502894 0.176370 0.595273 0.027 Uiso calc 1 . .
    C C9 0.48849(14) 0.3425(5) 0.7279(3) 0.0226(6) Uani d 1 . .
    H H9A 0.463338 0.230491 0.754515 0.027 Uiso calc 1 . .
    H H9B 0.512849 0.393847 0.784358 0.027 Uiso calc 1 . .
    C C10 0.43476(15) 0.6603(5) 0.7715(3) 0.0222(6) Uani d 1 . .
    H H10A 0.415201 0.578917 0.825322 0.027 Uiso calc 1 . .
    H H10B 0.406761 0.762946 0.744670 0.027 Uiso calc 1 . .
    C C11 0.48557(16) 0.7759(6) 0.8177(3) 0.0283(7) Uani d 1 . .
    H H11A 0.471804 0.867734 0.872038 0.043 Uiso calc 1 . .
    H H11B 0.513054 0.675182 0.845802 0.043 Uiso calc 1 . .
    H H11C 0.504613 0.859261 0.765128 0.043 Uiso calc 1 . .
    C C12 0.40028(13) 0.4385(5) 0.6321(2) 0.0222(6) Uani d 1 . .
    H H12A 0.413673 0.356314 0.572965 0.027 Uiso calc 1 . .
    H H12B 0.378887 0.560191 0.605402 0.027 Uiso calc 1 . .
    C C13 0.35861(15) 0.3051(6) 0.6926(3) 0.0319(8) Uani d 1 . .
    H H13A 0.324823 0.272829 0.650745 0.048 Uiso calc 1 . .
    H H13B 0.346350 0.381139 0.753507 0.048 Uiso calc 1 . .
    H H13C 0.377714 0.175336 0.712744 0.048 Uiso calc 1 . .
    C C14 0.42161(12) 0.8351(5) 0.4727(2) 0.0170(5) Uani d 1 . .
    C C15 0.37829(13) 0.9942(5) 0.4325(2) 0.0215(6) Uani d 1 . .
    H H15A 0.351429 1.028904 0.488492 0.026 Uiso calc 1 . .
    H H15B 0.399690 1.123004 0.415505 0.026 Uiso calc 1 . .
    C C16 0.34295(12) 0.9344(5) 0.3416(2) 0.0192(5) Uani d 1 . .
    C C17 0.33190(13) 1.0802(5) 0.2656(2) 0.0212(6) Uani d 1 . .
    H H17A 0.350911 1.211234 0.267692 0.025 Uiso calc 1 . .
    C C18 0.29376(14) 1.0383(6) 0.1867(3) 0.0258(6) Uani d 1 . .
    H H18A 0.286285 1.140770 0.136301 0.031 Uiso calc 1 . .
    C C19 0.26675(14) 0.8464(6) 0.1823(3) 0.0278(7) Uani d 1 . .
    H H19A 0.240039 0.817626 0.129361 0.033 Uiso calc 1 . .
    C C20 0.27865(15) 0.6955(6) 0.2551(3) 0.0275(7) Uani d 1 . .
    H H20A 0.260772 0.562618 0.250909 0.033 Uiso calc 1 . .
    C C21 0.31655(13) 0.7385(5) 0.3340(3) 0.0226(6) Uani d 1 . .
    H H21A 0.324698 0.634210 0.383164 0.027 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    Cu O1 . 1.909(2) ?
    Cu N1 . 1.923(2) ?
    Cu O2 . 1.957(2) ?
    Cu N2 . 2.068(2) ?
    Cu O3 . 2.604(2) ?
    O1 C1 . 1.299(3) ?
    O2 C14 . 1.292(4) ?
    O3 C14 . 1.228(4) ?
    N1 C7 . 1.287(3) ?
    N1 C8 . 1.467(4) ?
    N2 C10 . 1.490(4) ?
    N2 C9 . 1.495(4) ?
    N2 C12 . 1.497(4) ?
    C1 C2 . 1.423(4) ?
    C1 C6 . 1.424(4) ?
    C2 C3 . 1.368(4) ?
    C2 H2A . 0.9500 ?
    C3 C4 . 1.402(4) ?
    C3 H3A . 0.9500 ?
    C4 C5 . 1.379(4) ?
    C4 H4A . 0.9500 ?
    C5 C6 . 1.408(4) ?
    C5 H5A . 0.9500 ?
    C6 C7 . 1.441(4) ?
    C7 H7A . 0.9500 ?
    C8 C9 . 1.509(5) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 C11 . 1.519(5) ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
    C12 C13 . 1.517(4) ?
    C12 H12A . 0.9900 ?
    C12 H12B . 0.9900 ?
    C13 H13A . 0.9800 ?
    C13 H13B . 0.9800 ?
    C13 H13C . 0.9800 ?
    C14 C15 . 1.526(4) ?
    C15 C16 . 1.500(4) ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C16 C17 . 1.394(4) ?
    C16 C21 . 1.402(4) ?
    C17 C18 . 1.390(5) ?
    C17 H17A . 0.9500 ?
    C18 C19 . 1.383(5) ?
    C18 H18A . 0.9500 ?
    C19 C20 . 1.390(5) ?
    C19 H19A . 0.9500 ?
    C20 C21 . 1.387(5) ?
    C20 H20A . 0.9500 ?
    C21 H21A . 0.9500 ?
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 Cu N1 . . 93.49(9) ?
    O1 Cu O2 . . 90.51(9) ?
    N1 Cu O2 . . 171.79(10) ?
    O1 Cu N2 . . 166.33(11) ?
    N1 Cu N2 . . 85.17(10) ?
    O2 Cu N2 . . 92.61(9) ?
    O1 Cu O3 . . 91.81(9) ?
    N1 Cu O3 . . 116.37(10) ?
    O2 Cu O3 . . 56.27(8) ?
    N2 Cu O3 . . 100.98(9) ?
    C1 O1 Cu . . 127.30(19) ?
    C14 O2 Cu . . 103.79(18) ?
    C14 O3 Cu . . 75.67(17) ?
    C7 N1 C8 . . 120.5(2) ?
    C7 N1 Cu . . 126.6(2) ?
    C8 N1 Cu . . 112.84(18) ?
    C10 N2 C9 . . 110.8(3) ?
    C10 N2 C12 . . 110.6(2) ?
    C9 N2 C12 . . 112.0(2) ?
    C10 N2 Cu . . 110.60(19) ?
    C9 N2 Cu . . 106.15(18) ?
    C12 N2 Cu . . 106.56(18) ?
    O1 C1 C2 . . 118.6(3) ?
    O1 C1 C6 . . 124.8(3) ?
    C2 C1 C6 . . 116.6(3) ?
    C3 C2 C1 . . 122.1(3) ?
    C3 C2 H2A . . 119.0 ?
    C1 C2 H2A . . 119.0 ?
    C2 C3 C4 . . 121.0(3) ?
    C2 C3 H3A . . 119.5 ?
    C4 C3 H3A . . 119.5 ?
    C5 C4 C3 . . 118.6(3) ?
    C5 C4 H4A . . 120.7 ?
    C3 C4 H4A . . 120.7 ?
    C4 C5 C6 . . 121.6(3) ?
    C4 C5 H5A . . 119.2 ?
    C6 C5 H5A . . 119.2 ?
    C5 C6 C1 . . 120.1(3) ?
    C5 C6 C7 . . 117.4(3) ?
    C1 C6 C7 . . 122.4(3) ?
    N1 C7 C6 . . 125.2(3) ?
    N1 C7 H7A . . 117.4 ?
    C6 C7 H7A . . 117.4 ?
    N1 C8 C9 . . 107.2(3) ?
    N1 C8 H8A . . 110.3 ?
    C9 C8 H8A . . 110.3 ?
    N1 C8 H8B . . 110.3 ?
    C9 C8 H8B . . 110.3 ?
    H8A C8 H8B . . 108.5 ?
    N2 C9 C8 . . 110.0(3) ?
    N2 C9 H9A . . 109.7 ?
    C8 C9 H9A . . 109.7 ?
    N2 C9 H9B . . 109.7 ?
    C8 C9 H9B . . 109.7 ?
    H9A C9 H9B . . 108.2 ?
    N2 C10 C11 . . 112.8(3) ?
    N2 C10 H10A . . 109.0 ?
    C11 C10 H10A . . 109.0 ?
    N2 C10 H10B . . 109.0 ?
    C11 C10 H10B . . 109.0 ?
    H10A C10 H10B . . 107.8 ?
    C10 C11 H11A . . 109.5 ?
    C10 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C10 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    N2 C12 C13 . . 116.4(3) ?
    N2 C12 H12A . . 108.2 ?
    C13 C12 H12A . . 108.2 ?
    N2 C12 H12B . . 108.2 ?
    C13 C12 H12B . . 108.2 ?
    H12A C12 H12B . . 107.4 ?
    C12 C13 H13A . . 109.5 ?
    C12 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    C12 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    O3 C14 O2 . . 124.0(3) ?
    O3 C14 C15 . . 122.4(3) ?
    O2 C14 C15 . . 113.6(3) ?
    C16 C15 C14 . . 117.7(3) ?
    C16 C15 H15A . . 107.9 ?
    C14 C15 H15A . . 107.9 ?
    C16 C15 H15B . . 107.9 ?
    C14 C15 H15B . . 107.9 ?
    H15A C15 H15B . . 107.2 ?
    C17 C16 C21 . . 118.0(3) ?
    C17 C16 C15 . . 120.1(3) ?
    C21 C16 C15 . . 121.7(3) ?
    C18 C17 C16 . . 121.6(3) ?
    C18 C17 H17A . . 119.2 ?
    C16 C17 H17A . . 119.2 ?
    C19 C18 C17 . . 119.5(3) ?
    C19 C18 H18A . . 120.3 ?
    C17 C18 H18A . . 120.3 ?
    C18 C19 C20 . . 120.1(3) ?
    C18 C19 H19A . . 120.0 ?
    C20 C19 H19A . . 120.0 ?
    C21 C20 C19 . . 120.2(3) ?
    C21 C20 H20A . . 119.9 ?
    C19 C20 H20A . . 119.9 ?
    C20 C21 C16 . . 120.6(3) ?
    C20 C21 H21A . . 119.7 ?
    C16 C21 H21A . . 119.7 ?
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
    Cu O1 C1 C2 . . . . -178.1(2) ?
    Cu O1 C1 C6 . . . . 1.5(4) ?
    O1 C1 C2 C3 . . . . 179.7(3) ?
    C6 C1 C2 C3 . . . . 0.0(4) ?
    C1 C2 C3 C4 . . . . 0.1(5) ?
    C2 C3 C4 C5 . . . . 0.2(5) ?
    C3 C4 C5 C6 . . . . -0.7(5) ?
    C4 C5 C6 C1 . . . . 0.8(5) ?
    C4 C5 C6 C7 . . . . -179.0(3) ?
    O1 C1 C6 C5 . . . . 179.9(3) ?
    C2 C1 C6 C5 . . . . -0.5(4) ?
    O1 C1 C6 C7 . . . . -0.4(5) ?
    C2 C1 C6 C7 . . . . 179.3(3) ?
    C8 N1 C7 C6 . . . . 179.2(3) ?
    Cu N1 C7 C6 . . . . -4.0(4) ?
    C5 C6 C7 N1 . . . . -178.5(3) ?
    C1 C6 C7 N1 . . . . 1.7(5) ?
    C7 N1 C8 C9 . . . . 139.9(3) ?
    Cu N1 C8 C9 . . . . -37.3(3) ?
    C10 N2 C9 C8 . . . . -155.3(3) ?
    C12 N2 C9 C8 . . . . 80.7(3) ?
    Cu N2 C9 C8 . . . . -35.2(3) ?
    N1 C8 C9 N2 . . . . 47.6(3) ?
    C9 N2 C10 C11 . . . . 66.1(3) ?
    C12 N2 C10 C11 . . . . -169.2(3) ?
    Cu N2 C10 C11 . . . . -51.4(3) ?
    C10 N2 C12 C13 . . . . -64.0(4) ?
    C9 N2 C12 C13 . . . . 60.1(4) ?
    Cu N2 C12 C13 . . . . 175.8(3) ?
    Cu O3 C14 O2 . . . . -4.8(2) ?
    Cu O3 C14 C15 . . . . 175.4(3) ?
    Cu O2 C14 O3 . . . . 6.4(3) ?
    Cu O2 C14 C15 . . . . -173.84(19) ?
    O3 C14 C15 C16 . . . . 10.0(4) ?
    O2 C14 C15 C16 . . . . -169.8(3) ?
    C14 C15 C16 C17 . . . . -139.8(3) ?
    C14 C15 C16 C21 . . . . 45.1(4) ?
    C21 C16 C17 C18 . . . . 3.1(5) ?
    C15 C16 C17 C18 . . . . -172.1(3) ?
    C16 C17 C18 C19 . . . . -1.2(5) ?
    C17 C18 C19 C20 . . . . -1.2(5) ?
    C18 C19 C20 C21 . . . . 1.6(5) ?
    C19 C20 C21 C16 . . . . 0.5(5) ?
    C17 C16 C21 C20 . . . . -2.8(5) ?
    C15 C16 C21 C20 . . . . 172.4(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
    _geom_hbond_publ_flag
    C8 H8B O2 1_545 0.99 2.37 3.260(4) 149.4 yes
    C9 H9B O3 2_665 0.99 2.28 3.172(4) 149.1 yes
    C12 H12B O2 . 0.99 2.64 3.183(4) 114.8 yes
_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     ?
_shelx_estimated_absorpt_T_max     ?
data_3
_audit_creation_method     'SHELXL-2018/3'
_database_code_depnum_ccdc_archive     'CCDC 1901536'
_chemical_name_systematic
;\
Bis[μ-(E)-2-({[3-(diethylamino)propyl]imino}methyl)phenolato]-\
κ⁴N,N',O:O;κ⁴O:N,N',\
O-(μ-2-methylbenzoato-κ²O:O')copper(II) perchlorate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C32 H41 Cu2 N4 O4 +, Cl O4 -'
_chemical_formula_sum     'C32 H41 Cl Cu2 N4 O8'
_chemical_formula_iupac     '[Cu2 (C8 H7 O2) (C12 H17 N2 O)2] Cl O4'
_chemical_formula_weight     772.22
_chemical_melting_point     ?
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P b c a'
_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    'x, -y-1/2, z-1/2'
    '-x-1/2, y-1/2, z'
_cell_length_a     10.51085(16)
_cell_length_b     22.2419(5)
_cell_length_c     28.8403(5)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     6742.3(2)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     21097
_cell_measurement_theta_min     3.7240
_cell_measurement_theta_max     36.3840
_cell_measurement_temperature     100(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     green-blue
_exptl_crystal_size_max     0.258
_exptl_crystal_size_mid     0.213
_exptl_crystal_size_min     0.031
_exptl_crystal_density_diffrn     1.521
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     3200
_exptl_absorpt_coefficient_mu     1.397
_exptl_absorpt_correction_type     gaussian
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2018)
;
_exptl_absorpt_correction_T_min     0.614
_exptl_absorpt_correction_T_max     1.000
_diffrn_ambient_temperature     100(2)
_diffrn_source     'micro-focus sealed X-ray tube'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type
         'Rigaku OD SuperNova Dual source diffractometer with an Atlas detector'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     10.6501
_diffrn_reflns_number     154652
_diffrn_reflns_av_R_equivalents     0.0897
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_theta_min     3.367
_diffrn_reflns_theta_max     41.558
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.961
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -18
_diffrn_reflns_limit_h_max     19
_diffrn_reflns_limit_k_min     -33
_diffrn_reflns_limit_k_max     40
_diffrn_reflns_limit_l_min     -35
_diffrn_reflns_limit_l_max     52
_refine_special_details     ?
_reflns_number_total     22070
_reflns_number_gt     12413
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1200
_refine_ls_R_factor_gt     0.0527
_refine_ls_wR_factor_gt     0.1031
_refine_ls_wR_factor_ref     0.1349
_refine_ls_goodness_of_fit_ref     1.035
_refine_ls_restrained_S_all     1.034
_refine_ls_number_reflns     22070
_refine_ls_number_parameters     467
_refine_ls_number_restraints     44
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0390P)²+5.3824P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     1.134
_refine_diff_density_min     -1.105
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
    'Cl' 'Cl' 0.1484 0.1585
                         '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'
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
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 0.28173(2) 1.08502(2) 0.16413(2) 0.01838(4) Uani d 1 . .
    Cu Cu2 0.32761(2) 0.99599(2) 0.08706(2) 0.01958(4) Uani d 1 . .
    O O1 0.18853(12) 1.01143(6) 0.14771(5) 0.0219(2) Uani d 1 . .
    O O2 0.44003(11) 1.05731(6) 0.11374(5) 0.0215(2) Uani d 1 . .
    O O3 0.18608(13) 1.12125(6) 0.11331(5) 0.0241(3) Uani d 1 . .
    O O4 0.24510(13) 1.06268(6) 0.05351(5) 0.0255(3) Uani d 1 . .
    N N1 0.32825(14) 1.17468(7) 0.18137(6) 0.0223(3) Uani d 1 . .
    N N2 0.35486(14) 1.04593(7) 0.21946(5) 0.0229(3) Uani d 1 . .
    N N3 0.42640(14) 0.93093(7) 0.11619(6) 0.0232(3) Uani d 1 . .
    N N4 0.24861(19) 0.93856(9) 0.03741(7) 0.0353(4) Uani d 1 . .
    C C1 0.15786(15) 0.96685(8) 0.17591(6) 0.0204(3) Uani d 1 . .
    C C2 0.06056(16) 0.92586(8) 0.16282(8) 0.0259(3) Uani d 1 . .
    H H2A 0.018193 0.931168 0.134018 0.031 Uiso calc 1 . .
    C C3 0.02630(19) 0.87838(9) 0.19118(9) 0.0326(4) Uani d 1 . .
    H H3A -0.040146 0.852123 0.181767 0.039 Uiso calc 1 . .
    C C4 0.0877(2) 0.86842(10) 0.23339(9) 0.0377(5) Uani d 1 . .
    H H4A 0.063932 0.835617 0.252624 0.045 Uiso calc 1 . .
    C C5 0.1835(2) 0.90699(10) 0.24663(8) 0.0340(4) Uani d 1 . .
    H H5A 0.226834 0.900052 0.275026 0.041 Uiso calc 1 . .
    C C6 0.21861(18) 0.95663(8) 0.21897(7) 0.0238(3) Uani d 1 . .
    C C7 0.31918(17) 0.99510(8) 0.23622(7) 0.0235(3) Uani d 1 . .
    H H7A 0.363661 0.981258 0.262830 0.028 Uiso calc 1 . .
    C C8 0.45833(19) 1.07664(10) 0.24478(7) 0.0305(4) Uani d 1 . .
    H H8A 0.535325 1.078379 0.225058 0.037 Uiso calc 1 . .
    H H8B 0.479509 1.053689 0.273162 0.037 Uiso calc 1 . .
    C C9 0.4179(2) 1.13985(10) 0.25785(7) 0.0310(4) Uani d 1 . .
    H H9A 0.328741 1.138993 0.268907 0.037 Uiso calc 1 . .
    H H9B 0.471883 1.154315 0.283668 0.037 Uiso calc 1 . .
    C C10 0.42827(18) 1.18331(10) 0.21765(7) 0.0297(4) Uani d 1 . .
    H H10A 0.422390 1.224879 0.229733 0.036 Uiso calc 1 . .
    H H10B 0.512998 1.178625 0.203100 0.036 Uiso calc 1 . .
    C C11 0.20745(19) 1.20172(11) 0.19811(8) 0.0338(5) Uani d 1 . .
    H H11A 0.220059 1.244773 0.203678 0.051 Uiso calc 1 . .
    H H11B 0.181586 1.182086 0.227028 0.051 Uiso calc 1 . .
    H H11C 0.141026 1.196136 0.174653 0.051 Uiso calc 1 . .
    C C12 0.3685(2) 1.21036(10) 0.14034(8) 0.0314(4) Uani d 1 . .
    H H12A 0.390609 1.251243 0.150133 0.047 Uiso calc 1 . .
    H H12B 0.298717 1.212011 0.117853 0.047 Uiso calc 1 . .
    H H12C 0.442856 1.191360 0.125973 0.047 Uiso calc 1 . .
    C C13 0.56329(16) 1.04925(8) 0.12129(6) 0.0195(3) Uani d 1 . .
    C C14 0.64547(17) 1.09933(8) 0.12300(7) 0.0232(3) Uani d 1 . .
    H H14A 0.611230 1.138621 0.119659 0.028 Uiso calc 1 . .
    C C15 0.77541(17) 1.09226(9) 0.12948(7) 0.0243(3) Uani d 1 . .
    H H15A 0.828659 1.126763 0.130131 0.029 Uiso calc 1 . .
    C C16 0.82929(17) 1.03539(9) 0.13505(8) 0.0273(4) Uani d 1 . .
    H H16A 0.918577 1.030819 0.138755 0.033 Uiso calc 1 . .
    C C17 0.75007(18) 0.98594(9) 0.13505(8) 0.0276(4) Uani d 1 . .
    H H17A 0.785487 0.947130 0.139803 0.033 Uiso calc 1 . .
    C C18 0.61758(16) 0.99162(8) 0.12815(6) 0.0216(3) Uani d 1 . .
    C C19 0.54316(17) 0.93722(8) 0.12929(7) 0.0247(3) Uani d 1 . .
    H H19A 0.584320 0.902305 0.140915 0.030 Uiso calc 1 . .
    C C20 0.37186(19) 0.87002(9) 0.12140(8) 0.0295(4) Uani d 1 . .
    H H20A 0.294207 0.872019 0.140770 0.035 Uiso calc 1 . .
    H H20B 0.433996 0.843546 0.137170 0.035 Uiso calc 1 . .
    C C21 0.3391(2) 0.84414(11) 0.07424(11) 0.0425(6) Uani d 1 . .
    H H21A 0.414251 0.847807 0.053734 0.051 Uiso calc 1 . .
    H H21B 0.319906 0.800810 0.077773 0.051 Uiso calc 1 . .
    C C22 0.2275(3) 0.87454(11) 0.05142(10) 0.0431(6) Uani d 1 . .
    H H22A 0.203933 0.851222 0.023480 0.052 Uiso calc 1 . .
    H H22B 0.154364 0.873092 0.073008 0.052 Uiso calc 1 . .
    C C23 0.3397(3) 0.94346(15) -0.00141(10) 0.0532(7) Uani d 1 . .
    H H23A 0.309784 0.919079 -0.027527 0.080 Uiso calc 1 . .
    H H23B 0.423371 0.928975 0.008627 0.080 Uiso calc 1 . .
    H H23C 0.346501 0.985575 -0.011092 0.080 Uiso calc 1 . .
    C C24 0.1215(3) 0.95918(14) 0.02074(11) 0.0534(7) Uani d 1 . .
    H H24A 0.089533 0.931073 -0.002688 0.080 Uiso calc 1 . .
    H H24B 0.129479 0.999341 0.007071 0.080 Uiso calc 1 . .
    H H24C 0.062063 0.960663 0.046891 0.080 Uiso calc 1 . .
    C C25 0.19144(16) 1.10812(8) 0.07068(6) 0.0209(3) Uani d 1 . .
    C C26 0.12577(17) 1.15150(8) 0.03844(6) 0.0220(3) Uani d 1 . .
    C C27 0.02568(18) 1.18557(9) 0.05705(7) 0.0259(3) Uani d 1 . .
    H H27A 0.003035 1.180622 0.088715 0.031 Uiso calc 1 . .
    C C28 -0.0408(2) 1.22642(10) 0.02983(8) 0.0333(4) Uani d 1 . .
    H H28A -0.110083 1.248384 0.042477 0.040 Uiso calc 1 . .
    C C29 -0.0050(2) 1.23482(10) -0.01588(9) 0.0388(5) Uani d 1 . .
    H H29A -0.048923 1.263227 -0.034560 0.047 Uiso calc 1 . .
    C C30 0.0943(2) 1.20205(11) -0.03445(8) 0.0358(5) Uani d 1 . .
    H H30A 0.117859 1.208614 -0.065840 0.043 Uiso calc 1 . .
    C C31 0.16139(19) 1.15931(9) -0.00827(7) 0.0277(4) Uani d 1 . .
    C C32 0.2693(2) 1.12608(12) -0.03120(8) 0.0384(5) Uani d 1 . .
    H H32A 0.290621 1.145716 -0.060613 0.058 Uiso calc 1 . .
    H H32B 0.243726 1.084418 -0.037115 0.058 Uiso calc 1 . .
    H H32C 0.343858 1.126512 -0.010781 0.058 Uiso calc 1 . .
    Cl Cl1 0.71528(4) 0.76845(2) 0.15982(2) 0.02309(8) Uani d 1 . .
    O O11A 0.7359(13) 0.8310(3) 0.1481(5) 0.0305(14) Uani d 0.64(4) A 1
    O O12A 0.5835(7) 0.7574(6) 0.1677(4) 0.0448(17) Uani d 0.64(4) A 1
    O O13A 0.7872(10) 0.7544(7) 0.2006(4) 0.054(2) Uani d 0.64(4) A 1
    O O14A 0.7590(13) 0.7325(4) 0.1220(4) 0.059(2) Uani d 0.64(4) A 1
    O O11B 0.752(2) 0.8298(6) 0.1535(9) 0.030(2) Uani d 0.36(4) A 2
    O O12B 0.5852(13) 0.7673(13) 0.1760(10) 0.058(5) Uani d 0.36(4) A 2
    O O13B 0.7955(17) 0.7392(9) 0.1922(7) 0.053(3) Uani d 0.36(4) A 2
    O O14B 0.722(3) 0.7377(9) 0.1163(5) 0.068(4) Uani d 0.36(4) A 2
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 . 1.9514(13) ?
    Cu1 O1 . 1.9654(13) ?
    Cu1 N2 . 1.9731(15) ?
    Cu1 N1 . 2.1126(16) ?
    Cu1 O2 . 2.2935(13) ?
    Cu1 Cu2 . 3.0155(3) ?
    Cu2 O2 . 1.9615(13) ?
    Cu2 N3 . 1.9693(15) ?
    Cu2 O4 . 1.9719(14) ?
    Cu2 N4 . 2.0909(18) ?
    Cu2 O1 . 2.3053(14) ?
    O1 C1 . 1.322(2) ?
    O2 C13 . 1.326(2) ?
    O3 C25 . 1.265(2) ?
    O4 C25 . 1.259(2) ?
    N1 C11 . 1.485(2) ?
    N1 C12 . 1.486(3) ?
    N1 C10 . 1.496(3) ?
    N2 C7 . 1.285(2) ?
    N2 C8 . 1.477(2) ?
    N3 C19 . 1.292(2) ?
    N3 C20 . 1.479(2) ?
    N4 C23 . 1.478(4) ?
    N4 C24 . 1.492(3) ?
    N4 C22 . 1.497(3) ?
    C1 C6 . 1.415(3) ?
    C1 C2 . 1.421(2) ?
    C2 C3 . 1.383(3) ?
    C2 H2A . 0.9500 ?
    C3 C4 . 1.396(4) ?
    C3 H3A . 0.9500 ?
    C4 C5 . 1.376(3) ?
    C4 H4A . 0.9500 ?
    C5 C6 . 1.411(3) ?
    C5 H5A . 0.9500 ?
    C6 C7 . 1.448(3) ?
    C7 H7A . 0.9500 ?
    C8 C9 . 1.516(3) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C9 C10 . 1.513(3) ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
    C12 H12A . 0.9800 ?
    C12 H12B . 0.9800 ?
    C12 H12C . 0.9800 ?
    C13 C14 . 1.410(2) ?
    C13 C18 . 1.417(2) ?
    C14 C15 . 1.387(2) ?
    C14 H14A . 0.9500 ?
    C15 C16 . 1.395(3) ?
    C15 H15A . 0.9500 ?
    C16 C17 . 1.379(3) ?
    C16 H16A . 0.9500 ?
    C17 C18 . 1.412(3) ?
    C17 H17A . 0.9500 ?
    C18 C19 . 1.441(3) ?
    C19 H19A . 0.9500 ?
    C20 C21 . 1.517(4) ?
    C20 H20A . 0.9900 ?
    C20 H20B . 0.9900 ?
    C21 C22 . 1.505(4) ?
    C21 H21A . 0.9900 ?
    C21 H21B . 0.9900 ?
    C22 H22A . 0.9900 ?
    C22 H22B . 0.9900 ?
    C23 H23A . 0.9800 ?
    C23 H23B . 0.9800 ?
    C23 H23C . 0.9800 ?
    C24 H24A . 0.9800 ?
    C24 H24B . 0.9800 ?
    C24 H24C . 0.9800 ?
    C25 C26 . 1.507(2) ?
    C26 C27 . 1.403(3) ?
    C26 C31 . 1.409(3) ?
    C27 C28 . 1.389(3) ?
    C27 H27A . 0.9500 ?
    C28 C29 . 1.383(4) ?
    C28 H28A . 0.9500 ?
    C29 C30 . 1.381(4) ?
    C29 H29A . 0.9500 ?
    C30 C31 . 1.404(3) ?
    C30 H30A . 0.9500 ?
    C31 C32 . 1.507(3) ?
    C32 H32A . 0.9800 ?
    C32 H32B . 0.9800 ?
    C32 H32C . 0.9800 ?
    Cl1 O13B . 1.417(11) ?
    Cl1 O12A . 1.425(7) ?
    Cl1 O11B . 1.428(12) ?
    Cl1 O14A . 1.430(6) ?
    Cl1 O14B . 1.433(11) ?
    Cl1 O13A . 1.433(7) ?
    Cl1 O12B . 1.445(12) ?
    Cl1 O11A . 1.448(7) ?
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 . . 84.62(6) ?
    O3 Cu1 N2 . . 171.91(6) ?
    O1 Cu1 N2 . . 91.26(6) ?
    O3 Cu1 N1 . . 84.62(6) ?
    O1 Cu1 N1 . . 163.37(6) ?
    N2 Cu1 N1 . . 97.79(7) ?
    O3 Cu1 O2 . . 90.51(5) ?
    O1 Cu1 O2 . . 89.15(5) ?
    N2 Cu1 O2 . . 96.40(6) ?
    N1 Cu1 O2 . . 103.59(5) ?
    O3 Cu1 Cu2 . . 78.46(4) ?
    O1 Cu1 Cu2 . . 49.86(4) ?
    N2 Cu1 Cu2 . . 104.15(5) ?
    N1 Cu1 Cu2 . . 139.14(4) ?
    O2 Cu1 Cu2 . . 40.58(3) ?
    O2 Cu2 N3 . . 91.49(6) ?
    O2 Cu2 O4 . . 86.24(6) ?
    N3 Cu2 O4 . . 173.70(6) ?
    O2 Cu2 N4 . . 158.84(7) ?
    N3 Cu2 N4 . . 93.01(7) ?
    O4 Cu2 N4 . . 87.06(7) ?
    O2 Cu2 O1 . . 88.90(5) ?
    N3 Cu2 O1 . . 96.90(6) ?
    O4 Cu2 O1 . . 88.94(5) ?
    N4 Cu2 O1 . . 111.03(7) ?
    O2 Cu2 Cu1 . . 49.52(4) ?
    N3 Cu2 Cu1 . . 104.63(5) ?
    O4 Cu2 Cu1 . . 78.32(4) ?
    N4 Cu2 Cu1 . . 147.40(6) ?
    O1 Cu2 Cu1 . . 40.67(3) ?
    C1 O1 Cu1 . . 126.72(12) ?
    C1 O1 Cu2 . . 120.64(11) ?
    Cu1 O1 Cu2 . . 89.47(5) ?
    C13 O2 Cu2 . . 123.99(11) ?
    C13 O2 Cu1 . . 129.87(11) ?
    Cu2 O2 Cu1 . . 89.91(5) ?
    C25 O3 Cu1 . . 127.72(12) ?
    C25 O4 Cu2 . . 127.43(12) ?
    C11 N1 C12 . . 106.62(17) ?
    C11 N1 C10 . . 108.75(15) ?
    C12 N1 C10 . . 106.75(15) ?
    C11 N1 Cu1 . . 105.12(12) ?
    C12 N1 Cu1 . . 112.50(13) ?
    C10 N1 Cu1 . . 116.64(13) ?
    C7 N2 C8 . . 115.82(16) ?
    C7 N2 Cu1 . . 125.31(13) ?
    C8 N2 Cu1 . . 118.87(13) ?
    C19 N3 C20 . . 115.97(16) ?
    C19 N3 Cu2 . . 123.10(13) ?
    C20 N3 Cu2 . . 120.81(12) ?
    C23 N4 C24 . . 108.3(2) ?
    C23 N4 C22 . . 111.8(2) ?
    C24 N4 C22 . . 104.3(2) ?
    C23 N4 Cu2 . . 102.51(15) ?
    C24 N4 Cu2 . . 112.86(16) ?
    C22 N4 Cu2 . . 117.07(15) ?
    O1 C1 C6 . . 123.39(16) ?
    O1 C1 C2 . . 119.55(17) ?
    C6 C1 C2 . . 117.05(17) ?
    C3 C2 C1 . . 121.3(2) ?
    C3 C2 H2A . . 119.3 ?
    C1 C2 H2A . . 119.3 ?
    C2 C3 C4 . . 121.09(19) ?
    C2 C3 H3A . . 119.5 ?
    C4 C3 H3A . . 119.5 ?
    C5 C4 C3 . . 118.8(2) ?
    C5 C4 H4A . . 120.6 ?
    C3 C4 H4A . . 120.6 ?
    C4 C5 C6 . . 121.5(2) ?
    C4 C5 H5A . . 119.3 ?
    C6 C5 H5A . . 119.3 ?
    C5 C6 C1 . . 120.24(18) ?
    C5 C6 C7 . . 117.34(18) ?
    C1 C6 C7 . . 122.41(16) ?
    N2 C7 C6 . . 127.13(17) ?
    N2 C7 H7A . . 116.4 ?
    C6 C7 H7A . . 116.4 ?
    N2 C8 C9 . . 110.19(16) ?
    N2 C8 H8A . . 109.6 ?
    C9 C8 H8A . . 109.6 ?
    N2 C8 H8B . . 109.6 ?
    C9 C8 H8B . . 109.6 ?
    H8A C8 H8B . . 108.1 ?
    C10 C9 C8 . . 112.43(17) ?
    C10 C9 H9A . . 109.1 ?
    C8 C9 H9A . . 109.1 ?
    C10 C9 H9B . . 109.1 ?
    C8 C9 H9B . . 109.1 ?
    H9A C9 H9B . . 107.8 ?
    N1 C10 C9 . . 113.79(16) ?
    N1 C10 H10A . . 108.8 ?
    C9 C10 H10A . . 108.8 ?
    N1 C10 H10B . . 108.8 ?
    C9 C10 H10B . . 108.8 ?
    H10A C10 H10B . . 107.7 ?
    N1 C11 H11A . . 109.5 ?
    N1 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    N1 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    N1 C12 H12A . . 109.5 ?
    N1 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    N1 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    O2 C13 C14 . . 119.83(16) ?
    O2 C13 C18 . . 122.59(15) ?
    C14 C13 C18 . . 117.58(15) ?
    C15 C14 C13 . . 121.20(17) ?
    C15 C14 H14A . . 119.4 ?
    C13 C14 H14A . . 119.4 ?
    C14 C15 C16 . . 121.19(17) ?
    C14 C15 H15A . . 119.4 ?
    C16 C15 H15A . . 119.4 ?
    C17 C16 C15 . . 118.55(17) ?
    C17 C16 H16A . . 120.7 ?
    C15 C16 H16A . . 120.7 ?
    C16 C17 C18 . . 121.59(18) ?
    C16 C17 H17A . . 119.2 ?
    C18 C17 H17A . . 119.2 ?
    C17 C18 C13 . . 119.84(16) ?
    C17 C18 C19 . . 117.18(16) ?
    C13 C18 C19 . . 122.97(15) ?
    N3 C19 C18 . . 126.86(17) ?
    N3 C19 H19A . . 116.6 ?
    C18 C19 H19A . . 116.6 ?
    N3 C20 C21 . . 110.15(19) ?
    N3 C20 H20A . . 109.6 ?
    C21 C20 H20A . . 109.6 ?
    N3 C20 H20B . . 109.6 ?
    C21 C20 H20B . . 109.6 ?
    H20A C20 H20B . . 108.1 ?
    C22 C21 C20 . . 113.5(2) ?
    C22 C21 H21A . . 108.9 ?
    C20 C21 H21A . . 108.9 ?
    C22 C21 H21B . . 108.9 ?
    C20 C21 H21B . . 108.9 ?
    H21A C21 H21B . . 107.7 ?
    N4 C22 C21 . . 115.5(2) ?
    N4 C22 H22A . . 108.4 ?
    C21 C22 H22A . . 108.4 ?
    N4 C22 H22B . . 108.4 ?
    C21 C22 H22B . . 108.4 ?
    H22A C22 H22B . . 107.5 ?
    N4 C23 H23A . . 109.5 ?
    N4 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    N4 C23 H23C . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
    N4 C24 H24A . . 109.5 ?
    N4 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    N4 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 109.5 ?
    O4 C25 O3 . . 125.98(16) ?
    O4 C25 C26 . . 118.45(16) ?
    O3 C25 C26 . . 115.56(16) ?
    C27 C26 C31 . . 119.90(17) ?
    C27 C26 C25 . . 116.94(16) ?
    C31 C26 C25 . . 123.16(17) ?
    C28 C27 C26 . . 120.9(2) ?
    C28 C27 H27A . . 119.5 ?
    C26 C27 H27A . . 119.5 ?
    C29 C28 C27 . . 119.4(2) ?
    C29 C28 H28A . . 120.3 ?
    C27 C28 H28A . . 120.3 ?
    C30 C29 C28 . . 120.2(2) ?
    C30 C29 H29A . . 119.9 ?
    C28 C29 H29A . . 119.9 ?
    C29 C30 C31 . . 121.9(2) ?
    C29 C30 H30A . . 119.0 ?
    C31 C30 H30A . . 119.0 ?
    C30 C31 C26 . . 117.7(2) ?
    C30 C31 C32 . . 118.3(2) ?
    C26 C31 C32 . . 124.01(18) ?
    C31 C32 H32A . . 109.5 ?
    C31 C32 H32B . . 109.5 ?
    H32A C32 H32B . . 109.5 ?
    C31 C32 H32C . . 109.5 ?
    H32A C32 H32C . . 109.5 ?
    H32B C32 H32C . . 109.5 ?
    O13B Cl1 O11B . . 111.3(10) ?
    O12A Cl1 O14A . . 109.8(5) ?
    O13B Cl1 O14B . . 109.3(9) ?
    O11B Cl1 O14B . . 109.4(11) ?
    O12A Cl1 O13A . . 110.1(5) ?
    O14A Cl1 O13A . . 109.6(5) ?
    O13B Cl1 O12B . . 110.0(11) ?
    O11B Cl1 O12B . . 108.2(11) ?
    O14B Cl1 O12B . . 108.6(9) ?
    O12A Cl1 O11A . . 110.4(6) ?
    O14A Cl1 O11A . . 108.1(6) ?
    O13A Cl1 O11A . . 108.8(5) ?
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
    Cu1 O1 C1 C6 . . . . -19.3(2) ?
    Cu2 O1 C1 C6 . . . . 96.02(18) ?
    Cu1 O1 C1 C2 . . . . 161.71(13) ?
    Cu2 O1 C1 C2 . . . . -82.93(17) ?
    O1 C1 C2 C3 . . . . 179.52(17) ?
    C6 C1 C2 C3 . . . . 0.5(3) ?
    C1 C2 C3 C4 . . . . -1.1(3) ?
    C2 C3 C4 C5 . . . . 0.3(3) ?
    C3 C4 C5 C6 . . . . 1.2(4) ?
    C4 C5 C6 C1 . . . . -1.8(3) ?
    C4 C5 C6 C7 . . . . 179.1(2) ?
    O1 C1 C6 C5 . . . . -178.04(18) ?
    C2 C1 C6 C5 . . . . 0.9(3) ?
    O1 C1 C6 C7 . . . . 1.0(3) ?
    C2 C1 C6 C7 . . . . 179.95(17) ?
    C8 N2 C7 C6 . . . . 178.45(19) ?
    Cu1 N2 C7 C6 . . . . -0.9(3) ?
    C5 C6 C7 N2 . . . . -171.1(2) ?
    C1 C6 C7 N2 . . . . 9.9(3) ?
    C7 N2 C8 C9 . . . . -125.45(19) ?
    Cu1 N2 C8 C9 . . . . 54.0(2) ?
    N2 C8 C9 C10 . . . . -79.2(2) ?
    C11 N1 C10 C9 . . . . 77.9(2) ?
    C12 N1 C10 C9 . . . . -167.42(18) ?
    Cu1 N1 C10 C9 . . . . -40.7(2) ?
    C8 C9 C10 N1 . . . . 72.8(2) ?
    Cu2 O2 C13 C14 . . . . 155.33(13) ?
    Cu1 O2 C13 C14 . . . . -80.6(2) ?
    Cu2 O2 C13 C18 . . . . -25.1(2) ?
    Cu1 O2 C13 C18 . . . . 99.03(18) ?
    O2 C13 C14 C15 . . . . -178.08(17) ?
    C18 C13 C14 C15 . . . . 2.3(3) ?
    C13 C14 C15 C16 . . . . -0.7(3) ?
    C14 C15 C16 C17 . . . . -1.5(3) ?
    C15 C16 C17 C18 . . . . 2.0(3) ?
    C16 C17 C18 C13 . . . . -0.4(3) ?
    C16 C17 C18 C19 . . . . -179.3(2) ?
    O2 C13 C18 C17 . . . . 178.64(18) ?
    C14 C13 C18 C17 . . . . -1.7(3) ?
    O2 C13 C18 C19 . . . . -2.5(3) ?
    C14 C13 C18 C19 . . . . 177.14(18) ?
    C20 N3 C19 C18 . . . . -179.53(19) ?
    Cu2 N3 C19 C18 . . . . 4.4(3) ?
    C17 C18 C19 N3 . . . . -167.3(2) ?
    C13 C18 C19 N3 . . . . 13.8(3) ?
    C19 N3 C20 C21 . . . . -115.9(2) ?
    Cu2 N3 C20 C21 . . . . 60.3(2) ?
    N3 C20 C21 C22 . . . . -70.2(2) ?
    C23 N4 C22 C21 . . . . 69.0(3) ?
    C24 N4 C22 C21 . . . . -174.2(2) ?
    Cu2 N4 C22 C21 . . . . -48.7(3) ?
    C20 C21 C22 N4 . . . . 67.0(3) ?
    Cu2 O4 C25 O3 . . . . 4.0(3) ?
    Cu2 O4 C25 C26 . . . . -175.52(12) ?
    Cu1 O3 C25 O4 . . . . 11.9(3) ?
    Cu1 O3 C25 C26 . . . . -168.62(12) ?
    O4 C25 C26 C27 . . . . 153.93(18) ?
    O3 C25 C26 C27 . . . . -25.6(2) ?
    O4 C25 C26 C31 . . . . -26.8(3) ?
    O3 C25 C26 C31 . . . . 153.65(18) ?
    C31 C26 C27 C28 . . . . 1.1(3) ?
    C25 C26 C27 C28 . . . . -179.63(18) ?
    C26 C27 C28 C29 . . . . -1.9(3) ?
    C27 C28 C29 C30 . . . . 1.2(3) ?
    C28 C29 C30 C31 . . . . 0.4(4) ?
    C29 C30 C31 C26 . . . . -1.2(3) ?
    C29 C30 C31 C32 . . . . -179.4(2) ?
    C27 C26 C31 C30 . . . . 0.5(3) ?
    C25 C26 C31 C30 . . . . -178.74(18) ?
    C27 C26 C31 C32 . . . . 178.5(2) ?
    C25 C26 C31 C32 . . . . -0.7(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
    _geom_hbond_publ_flag
    C10 H10B O13A^a^ 8_765 0.99 2.69 3.418(12) 130.3 yes
    C10 H10B O13B^b^ 8_765 0.99 2.44 3.242(14) 137.5 yes
    C11 H11B O13A^a^ 3_655 0.98 2.65 3.148(8) 111.4 yes
    C11 H11C O3 . 0.98 2.48 3.039(2) 116.2 yes
    C12 H12B O3 . 0.98 2.34 2.866(3) 112.5 yes
    C14 H14A O14A^a^ 8_765 0.95 2.49 3.127(10) 124.0 yes
    C19 H19A O11A^a^ . 0.95 2.26 3.159(12) 158.1 yes
    C20 H20B O12A^a^ . 0.99 2.63 3.606(13) 169.0 yes
    C24 H24B O4 . 0.98 2.29 2.807(3) 111.7 yes
_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     ?
_shelx_estimated_absorpt_T_max     ?
data_global
_journal_date_recd_electronic     2018-12-20
_journal_date_accepted     2019-03-06
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2019
_journal_volume     75
_journal_issue      5
_journal_page_first     538
_journal_page_last     544
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2053229619003267
_journal_coeditor_code     FN3293
_publ_contact_author_name     'Ray J. Butcher'
_publ_contact_author_address
;
Department of Chemistry,
Howard University,
525 College Street NW,
Washington, DC 20059,
USA
;
_publ_contact_author_email     'rbutcher99@yahoo.com'
_publ_contact_author_fax     '202-806-5442'
_publ_contact_author_phone     '703-585-6631'
_publ_section_title
;
The crystal and molecular structures of three copper-containing complexes and
their activities in mimicking galactose oxidase
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Dimeska, Roza' .
;
School of Chemistry
University of Wollongong
Wollongong, NSW 2522
Australia
;
    'Wikaira, Jan' .
;
Department of Chemistry
University of Canterbury
Private Bag 4800
Christchurch 8140
New Zealand
;
    'Mockler, Garry M.' .
;
School of Chemistry
University of Wollongong
Wollongong, NSW 2522
Australia
;
    'Butcher, Ray J.' .
;
Department of Chemistry
Howard University
525 College Street NW
Washington
DC 20059
USA
;
_publ_section_synopsis
;
The structures of three copper-containing complexes are reported and tests for
their activity in the oxidation of D-galactose suggest that, unlike the
enzyme galactose oxidase, due to the precipitation of Cu₂O, this reaction is
not catalytic as would have been expected.
;
