#------------------------------------------------------------------------------
#$Date: 2023-04-05 13:55:50 +0300 (Wed, 05 Apr 2023) $
#$Revision: 282397 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/20/2312038.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_2312038
loop_
_publ_author_name
'Ranaweera, Samantha A.'
'Donnadieu, Bruno'
'Henry, William P.'
'White, Mark G.'
_publ_section_title
;
 Effects of electron-donating ability of binding sites on coordination
 number: the interactions of a cyclic Schiff base with copper ions.
;
_journal_coeditor_code           DG3038
_journal_issue                   'Pt 4'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              142
_journal_page_last               148
_journal_paper_doi               10.1107/S2053229623002280
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          '[Cu2 (C16 H20 N2 O4) (C5 H5 N1)]'
_chemical_formula_moiety         'C21 H25 Cu2 N3 O4'
_chemical_formula_sum            'C21 H25 Cu2 N3 O4'
_chemical_formula_weight         510.52
_chemical_name_systematic
'[μ-6,11-Dimethyl-7,10-diazahexadeca-5,11-diene-2,4,13,15-tetraolato(4-)-1κ⁴O²,O⁴,O¹³,O¹⁵:2κ⁴N⁷,N¹⁰,O⁴,O¹³](pyridine-1κN)dicopper(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   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/1
_cell_angle_alpha                106.4510(10)
_cell_angle_beta                 103.2710(10)
_cell_angle_gamma                91.4820(10)
_cell_formula_units_Z            2
_cell_length_a                   8.0549(5)
_cell_length_b                   9.8811(6)
_cell_length_c                   13.7189(8)
_cell_measurement_reflns_used    1540
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.497
_cell_measurement_theta_min      1.597
_cell_volume                     1014.40(11)
_computing_cell_refinement
;
APEX4 (Bruker, 2021)
;
_computing_data_collection
;
APEX4 (Bruker, 2021)
;
_computing_data_reduction
;
SAINT (Bruker, 2021)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020) and POV-Ray (Cason, 2004)
;
_computing_publication_material
;
APEX4 (Bruker, 2021)
;
_computing_structure_refinement
;
SHELXTL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'profile data from θ/2θ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12405
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.497
_diffrn_reflns_theta_min         1.597
_exptl_absorpt_coefficient_mu    2.131
_exptl_absorpt_correction_T_max  0.848
_exptl_absorpt_correction_T_min  0.567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_description       'prism frag'
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.309
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4680
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0205
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0266P)²+0.5267P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0540
_refine_ls_wR_factor_ref         0.0554
_reflns_number_gt                4293
_reflns_number_total             4680
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            dg3038sup1.cif
_cod_data_source_block           I
_cod_database_code               2312038
_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   0.567
_shelx_estimated_absorpt_t_max   0.848
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 0.67560(2) 0.69842(2) 0.78376(2) 0.01441(5) Uani d 1 . .
Cu Cu2 0.74398(2) 0.47982(2) 0.59601(2) 0.01529(5) Uani d 1 . .
N N1 0.84460(16) 0.30766(13) 0.57589(10) 0.0174(2) Uani d 1 . .
N N2 0.74679(16) 0.47544(14) 0.45833(10) 0.0187(3) Uani d 1 . .
N N3 0.94332(16) 0.81239(13) 0.84007(10) 0.0180(2) Uani d 1 . .
O O1 0.65027(13) 0.67677(11) 0.91465(8) 0.0181(2) Uani d 1 . .
O O2 0.74876(14) 0.50802(11) 0.74018(8) 0.0174(2) Uani d 1 . .
O O3 0.66075(14) 0.66147(11) 0.63315(8) 0.0183(2) Uani d 1 . .
O O4 0.55647(13) 0.86413(11) 0.78924(8) 0.0188(2) Uani d 1 . .
C C1 0.6968(2) 0.59164(17) 1.06208(12) 0.0215(3) Uani d 1 . .
H H1A 0.798563 0.647035 1.109045 0.032 Uiso calc 1 . .
H H1B 0.688525 0.500378 1.073311 0.032 Uiso calc 1 . .
H H1C 0.598137 0.639346 1.075005 0.032 Uiso calc 1 . .
C C2 0.70478(18) 0.57295(16) 0.94990(11) 0.0171(3) Uani d 1 . .
C C3 0.7684(2) 0.45196(16) 0.89819(12) 0.0191(3) Uani d 1 . .
H H3 0.802498 0.388154 0.935667 0.023 Uiso calc 1 . .
C C4 0.78706(18) 0.41521(15) 0.79329(11) 0.0165(3) Uani d 1 . .
C C5 0.8455(2) 0.28646(16) 0.74729(12) 0.0200(3) Uani d 1 . .
H H13 0.867341 0.225331 0.788305 0.024 Uiso calc 1 . .
C C6 0.87582(19) 0.23728(16) 0.64569(12) 0.0192(3) Uani d 1 . .
C C7 0.8840(2) 0.25573(17) 0.47290(12) 0.0213(3) Uani d 1 . .
H H7A 0.830832 0.159632 0.438267 0.026 Uiso calc 1 . .
H H7B 1.006961 0.253681 0.482675 0.026 Uiso calc 1 . .
C C8 0.8191(2) 0.35063(16) 0.40248(12) 0.0207(3) Uani d 1 . .
H H8A 0.913531 0.381478 0.378369 0.025 Uiso calc 1 . .
H H8B 0.732266 0.295644 0.341362 0.025 Uiso calc 1 . .
C C9 0.68559(19) 0.57112(17) 0.41322(12) 0.0194(3) Uani d 1 . .
C C10 0.6165(2) 0.69437(17) 0.46544(12) 0.0217(3) Uani d 1 . .
H H10 0.569839 0.751143 0.424439 0.026 Uiso calc 1 . .
C C11 0.61003(19) 0.74071(16) 0.57067(12) 0.0180(3) Uani d 1 . .
C C12 0.5485(2) 0.87312(16) 0.61445(12) 0.0207(3) Uani d 1 . .
H H12 0.521759 0.930978 0.571213 0.025 Uiso calc 1 . .
C C13 0.52491(18) 0.92382(16) 0.71465(12) 0.0189(3) Uani d 1 . .
C C14 0.4520(2) 1.06472(18) 0.74577(14) 0.0275(4) Uani d 1 . .
H H14A 0.346067 1.051050 0.764106 0.041 Uiso calc 1 . .
H H14B 0.431660 1.103913 0.688040 0.041 Uiso calc 1 . .
H H14C 0.532032 1.128651 0.804933 0.041 Uiso calc 1 . .
C C15 0.9508(2) 0.09704(18) 0.61936(14) 0.0276(4) Uani d 1 . .
H H15A 0.872528 0.030649 0.560754 0.041 Uiso calc 1 . .
H H15B 0.970034 0.061321 0.678814 0.041 Uiso calc 1 . .
H H15C 1.057625 0.109900 0.601769 0.041 Uiso calc 1 . .
C C16 0.6906(2) 0.55399(18) 0.30118(12) 0.0234(3) Uani d 1 . .
H H16A 0.807382 0.565340 0.297329 0.035 Uiso calc 1 . .
H H16B 0.628017 0.624467 0.276943 0.035 Uiso calc 1 . .
H H16C 0.639422 0.461260 0.257930 0.035 Uiso calc 1 . .
C C17 0.9586(2) 0.95341(16) 0.86038(12) 0.0210(3) Uani d 1 . .
H H17 0.861655 0.997153 0.839373 0.025 Uiso calc 1 . .
C C18 1.1110(2) 1.03733(17) 0.91091(13) 0.0241(3) Uani d 1 . .
H H18 1.115733 1.135193 0.924179 0.029 Uiso calc 1 . .
C C19 1.2563(2) 0.97349(18) 0.94140(14) 0.0276(4) Uani d 1 . .
H H19 1.360332 1.027555 0.976354 0.033 Uiso calc 1 . .
C C20 1.2440(2) 0.82729(19) 0.91890(14) 0.0293(4) Uani d 1 . .
H H20 1.340221 0.780985 0.936801 0.035 Uiso calc 1 . .
C C21 1.0856(2) 0.75152(17) 0.86922(13) 0.0222(3) Uani d 1 . .
H H21 1.077474 0.653523 0.855383 0.027 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
O4 Cu1 O1 . . 96.96(4) ?
O4 Cu1 O2 . . 163.66(5) ?
O1 Cu1 O2 . . 92.26(4) ?
O4 Cu1 O3 . . 91.98(4) ?
O1 Cu1 O3 . . 161.95(5) ?
O2 Cu1 O3 . . 75.68(4) ?
O4 Cu1 N3 . . 96.36(5) ?
O1 Cu1 N3 . . 98.64(5) ?
O2 Cu1 N3 . . 95.55(5) ?
O3 Cu1 N3 . . 95.90(5) ?
O4 Cu1 Cu2 . . 129.40(3) ?
O1 Cu1 Cu2 . . 129.34(3) ?
O2 Cu1 Cu2 . . 37.88(3) ?
O3 Cu1 Cu2 . . 37.87(3) ?
N3 Cu1 Cu2 . . 95.51(3) ?
N1 Cu2 N2 . . 89.11(5) ?
N1 Cu2 O3 . . 172.95(5) ?
N2 Cu2 O3 . . 96.15(5) ?
N1 Cu2 O2 . . 96.14(5) ?
N2 Cu2 O2 . . 173.15(5) ?
O3 Cu2 O2 . . 78.27(4) ?
N1 Cu2 Cu1 . . 134.73(4) ?
N2 Cu2 Cu1 . . 135.12(4) ?
O3 Cu2 Cu1 . . 39.35(3) ?
O2 Cu2 Cu1 . . 39.00(3) ?
C6 N1 C7 . . 122.22(13) ?
C6 N1 Cu2 . . 124.18(10) ?
C7 N1 Cu2 . . 113.59(10) ?
C9 N2 C8 . . 121.97(13) ?
C9 N2 Cu2 . . 124.47(11) ?
C8 N2 Cu2 . . 113.53(10) ?
C17 N3 C21 . . 117.19(13) ?
C17 N3 Cu1 . . 117.85(10) ?
C21 N3 Cu1 . . 124.18(10) ?
C2 O1 Cu1 . . 123.78(9) ?
C4 O2 Cu2 . . 126.53(9) ?
C4 O2 Cu1 . . 130.30(9) ?
Cu2 O2 Cu1 . . 103.12(5) ?
C11 O3 Cu2 . . 126.89(10) ?
C11 O3 Cu1 . . 130.31(10) ?
Cu2 O3 Cu1 . . 102.78(5) ?
C13 O4 Cu1 . . 124.28(10) ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O1 C2 C3 . . 128.09(13) ?
O1 C2 C1 . . 113.90(13) ?
C3 C2 C1 . . 118.01(13) ?
C2 C3 C4 . . 126.58(14) ?
C2 C3 H3 . . 116.7 ?
C4 C3 H3 . . 116.7 ?
O2 C4 C5 . . 120.43(13) ?
O2 C4 C3 . . 117.93(13) ?
C5 C4 C3 . . 121.63(14) ?
C4 C5 C6 . . 128.09(14) ?
C4 C5 H13 . . 116.0 ?
C6 C5 H13 . . 116.0 ?
N1 C6 C5 . . 123.86(14) ?
N1 C6 C15 . . 119.59(14) ?
C5 C6 C15 . . 116.55(14) ?
N1 C7 C8 . . 111.64(12) ?
N1 C7 H7A . . 109.3 ?
C8 C7 H7A . . 109.3 ?
N1 C7 H7B . . 109.3 ?
C8 C7 H7B . . 109.3 ?
H7A C7 H7B . . 108.0 ?
N2 C8 C7 . . 111.93(12) ?
N2 C8 H8A . . 109.2 ?
C7 C8 H8A . . 109.2 ?
N2 C8 H8B . . 109.2 ?
C7 C8 H8B . . 109.2 ?
H8A C8 H8B . . 107.9 ?
N2 C9 C10 . . 123.47(14) ?
N2 C9 C16 . . 119.63(14) ?
C10 C9 C16 . . 116.89(14) ?
C11 C10 C9 . . 128.15(14) ?
C11 C10 H10 . . 115.9 ?
C9 C10 H10 . . 115.9 ?
O3 C11 C10 . . 120.35(14) ?
O3 C11 C12 . . 117.70(13) ?
C10 C11 C12 . . 121.95(14) ?
C13 C12 C11 . . 126.53(14) ?
C13 C12 H12 . . 116.7 ?
C11 C12 H12 . . 116.7 ?
O4 C13 C12 . . 127.96(14) ?
O4 C13 C14 . . 113.09(13) ?
C12 C13 C14 . . 118.95(14) ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C6 C15 H15A . . 109.5 ?
C6 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C6 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C9 C16 H16A . . 109.5 ?
C9 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C9 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
N3 C17 C18 . . 123.38(15) ?
N3 C17 H17 . . 118.3 ?
C18 C17 H17 . . 118.3 ?
C19 C18 C17 . . 118.85(15) ?
C19 C18 H18 . . 120.6 ?
C17 C18 H18 . . 120.6 ?
C18 C19 C20 . . 118.67(15) ?
C18 C19 H19 . . 120.7 ?
C20 C19 H19 . . 120.7 ?
C21 C20 C19 . . 118.63(15) ?
C21 C20 H20 . . 120.7 ?
C19 C20 H20 . . 120.7 ?
N3 C21 C20 . . 123.25(15) ?
N3 C21 H21 . . 118.4 ?
C20 C21 H21 . . 118.4 ?
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 O4 . 1.9110(10) ?
Cu1 O1 . 1.9223(10) ?
Cu1 O2 . 1.9561(10) ?
Cu1 O3 . 1.9682(10) ?
Cu1 N3 . 2.2654(13) ?
Cu1 Cu2 . 3.0275(3) ?
Cu2 N1 . 1.8801(12) ?
Cu2 N2 . 1.8823(13) ?
Cu2 O3 . 1.9057(10) ?
Cu2 O2 . 1.9088(10) ?
N1 C6 . 1.319(2) ?
N1 C7 . 1.4711(19) ?
N2 C9 . 1.317(2) ?
N2 C8 . 1.4679(19) ?
N3 C17 . 1.3379(19) ?
N3 C21 . 1.3404(19) ?
O1 C2 . 1.2985(18) ?
O2 C4 . 1.3255(17) ?
O3 C11 . 1.3232(17) ?
O4 C13 . 1.2999(18) ?
C1 C2 . 1.514(2) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C3 . 1.383(2) ?
C3 C4 . 1.425(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.397(2) ?
C5 C6 . 1.420(2) ?
C5 H13 . 0.9300 ?
C6 C15 . 1.508(2) ?
C7 C8 . 1.547(2) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.425(2) ?
C9 C16 . 1.508(2) ?
C10 C11 . 1.399(2) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.429(2) ?
C12 C13 . 1.383(2) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.512(2) ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 C18 . 1.381(2) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.380(2) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.385(2) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.384(2) ?
C20 H20 . 0.9300 ?
C21 H21 . 0.9300 ?

_cod_database_fobs_code 2312038
