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#$Date: 2025-08-06 08:42:44 +0300 (Wed, 06 Aug 2025) $
#$Revision: 301663 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/53/1575332.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_1575332
loop_
_publ_author_name
'Mensing, Luca'
'Schäfer, Tim'
'Layh, Marcus'
'Hebenbrock, Marian'
_publ_section_title
;
 Gone with the Wind---Adducts of Volatile Pyridine Derivatives and
 Copper(II) Acetylacetonate
;
_journal_issue                   8
_journal_name_full               Crystals
_journal_page_first              690
_journal_paper_doi               10.3390/cryst15080690
_journal_volume                  15
_journal_year                    2025
_chemical_formula_sum            'C15 H19 Cu N O4'
_chemical_formula_weight         340.85
_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     'intrinsic phasing'
_audit_creation_method           SHELXL-2019/1
_cell_angle_alpha                93.9560(10)
_cell_angle_beta                 98.1740(10)
_cell_angle_gamma                117.6440(10)
_cell_formula_units_Z            2
_cell_length_a                   7.7444(3)
_cell_length_b                   8.1821(3)
_cell_length_c                   13.7360(5)
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.066
_cell_measurement_theta_min      2.844
_cell_volume                     754.10(5)
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_collection       'Bruker APEX5 2023/9-2'
_computing_data_reduction        'Bruker SAINT+'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Bruker Venture D8 with Photon III CMOS detector'
_diffrn_measurement_method       'f\ and w\ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11181
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.082
_diffrn_reflns_theta_min         2.844
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    1.462
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6394
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_description       fragment
_exptl_crystal_F_000             354
_exptl_crystal_size_max          0.444
_exptl_crystal_size_mid          0.173
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.698
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         4425
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0241
_refine_ls_R_factor_gt           0.0233
_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)+(0.0338P)²+0.4347P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0651
_refine_ls_wR_factor_ref         0.0656
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4291
_reflns_number_total             4425
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            Compound_1.cif
_cod_data_source_block           sad_a
_cod_database_code               1575332
_shelx_shelxl_version_number     2019/1
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.14148(2) 0.31299(2) 0.73259(2) 0.01044(5) Uani 1 1 d . . . . .
O1 O 0.22495(14) 0.24062(13) 0.61725(7) 0.01581(17) Uani 1 1 d . . . . .
O2 O 0.01793(14) 0.42079(13) 0.64402(7) 0.01573(17) Uani 1 1 d . . . . .
O3 O 0.00648(13) 0.33564(12) 0.83811(7) 0.01396(16) Uani 1 1 d . . . . .
O4 O 0.20261(13) 0.14736(12) 0.80903(7) 0.01440(16) Uani 1 1 d . . . . .
N1 N 0.42359(15) 0.57399(14) 0.79079(8) 0.01223(18) Uani 1 1 d . . . . .
C1 C 0.52485(18) 0.69642(17) 0.73344(9) 0.0156(2) Uani 1 1 d . . . . .
H1 H 0.475788 0.669255 0.663602 0.019 Uiso 1 1 calc R U . . .
C2 C 0.49480(18) 0.61410(17) 0.88889(9) 0.0139(2) Uani 1 1 d . . . . .
H2 H 0.422493 0.528665 0.930012 0.017 Uiso 1 1 calc R U . . .
C3 C 0.66901(18) 0.77418(17) 0.93377(9) 0.0158(2) Uani 1 1 d . . . . .
H3 H 0.716092 0.796710 1.003671 0.019 Uiso 1 1 calc R U . . .
C4 C 0.77250(18) 0.90042(17) 0.87370(10) 0.0174(2) Uani 1 1 d . . . . .
H4 H 0.891975 1.011739 0.901780 0.021 Uiso 1 1 calc R U . . .
C5 C 0.69843(19) 0.86120(18) 0.77197(10) 0.0189(2) Uani 1 1 d . . . . .
H5 H 0.765620 0.945973 0.729334 0.023 Uiso 1 1 calc R U . . .
C6 C 0.2691(2) 0.0460(2) 0.49996(10) 0.0216(3) Uani 1 1 d . . . . .
H6A H 0.202576 -0.089887 0.480664 0.032 Uiso 1 1 calc R U . . .
H6B H 0.411817 0.097506 0.501214 0.032 Uiso 1 1 calc R U . . .
H6C H 0.213447 0.100343 0.451723 0.032 Uiso 1 1 calc R U . . .
C7 C 0.23767(17) 0.09203(17) 0.60191(9) 0.0148(2) Uani 1 1 d . . . . .
C8 C -0.13808(18) 0.43107(16) 0.65342(9) 0.0144(2) Uani 1 1 d . . . . .
C9 C -0.22875(18) 0.39312(18) 0.73620(10) 0.0165(2) Uani 1 1 d . . . . .
H9 H -0.351945 0.393586 0.732530 0.020 Uiso 1 1 calc R U . . .
C10 C -0.14931(17) 0.35453(16) 0.82404(9) 0.0137(2) Uani 1 1 d . . . . .
C11 C 0.22653(19) -0.02837(18) 0.67159(10) 0.0175(2) Uani 1 1 d . . . . .
H11 H 0.226286 -0.141326 0.650005 0.021 Uiso 1 1 calc R U . . .
C12 C 0.21577(17) 0.00780(17) 0.77065(9) 0.0145(2) Uani 1 1 d . . . . .
C13 C -0.2245(2) 0.4941(2) 0.56809(11) 0.0230(3) Uani 1 1 d . . . . .
H13A H -0.362918 0.459059 0.570895 0.034 Uiso 1 1 calc R U . . .
H13B H -0.219617 0.434337 0.504979 0.034 Uiso 1 1 calc R U . . .
H13C H -0.147269 0.630067 0.572872 0.034 Uiso 1 1 calc R U . . .
C14 C -0.2498(2) 0.3378(2) 0.91190(10) 0.0204(2) Uani 1 1 d . . . . .
H14A H -0.385940 0.315157 0.889075 0.031 Uiso 1 1 calc R U . . .
H14B H -0.175670 0.453861 0.959496 0.031 Uiso 1 1 calc R U . . .
H14C H -0.253236 0.233564 0.944239 0.031 Uiso 1 1 calc R U . . .
C15 C 0.2225(2) -0.12413(19) 0.84072(11) 0.0205(2) Uani 1 1 d . . . . .
H15A H 0.198297 -0.240639 0.802201 0.031 Uiso 1 1 calc R U . . .
H15B H 0.119881 -0.150986 0.880736 0.031 Uiso 1 1 calc R U . . .
H15C H 0.353543 -0.066477 0.884735 0.031 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
_geom_angle_publ_flag
O2 Cu1 O1 86.94(4) . . ?
O2 Cu1 O3 92.20(4) . . ?
O1 Cu1 O3 167.88(4) . . ?
O2 Cu1 O4 165.58(4) . . ?
O1 Cu1 O4 91.71(4) . . ?
O3 Cu1 O4 86.11(4) . . ?
O2 Cu1 N1 96.78(4) . . ?
O1 Cu1 N1 96.31(4) . . ?
O3 Cu1 N1 95.80(4) . . ?
O4 Cu1 N1 97.64(4) . . ?
C7 O1 Cu1 124.71(8) . . ?
C8 O2 Cu1 124.84(8) . . ?
C10 O3 Cu1 124.12(8) . . ?
C12 O4 Cu1 124.43(8) . . ?
C2 N1 C1 117.96(11) . . ?
C2 N1 Cu1 118.33(8) . . ?
C1 N1 Cu1 123.69(8) . . ?
N1 C1 C5 122.60(11) . . ?
N1 C2 C3 123.39(11) . . ?
C4 C3 C2 118.18(11) . . ?
C5 C4 C3 118.85(11) . . ?
C1 C5 C4 119.00(11) . . ?
O1 C7 C11 125.45(11) . . ?
O1 C7 C6 115.88(11) . . ?
C11 C7 C6 118.67(11) . . ?
O2 C8 C9 125.22(11) . . ?
O2 C8 C13 115.63(11) . . ?
C9 C8 C13 119.13(11) . . ?
C8 C9 C10 124.06(11) . . ?
O3 C10 C9 125.59(11) . . ?
O3 C10 C14 115.73(11) . . ?
C9 C10 C14 118.66(11) . . ?
C12 C11 C7 123.94(11) . . ?
O4 C12 C11 125.31(11) . . ?
O4 C12 C15 115.69(11) . . ?
C11 C12 C15 119.00(11) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.9426(9) . ?
Cu1 O1 1.9483(9) . ?
Cu1 O3 1.9499(9) . ?
Cu1 O4 1.9528(9) . ?
Cu1 N1 2.2160(10) . ?
O1 C7 1.2704(15) . ?
O2 C8 1.2730(15) . ?
O3 C10 1.2758(14) . ?
O4 C12 1.2777(15) . ?
N1 C2 1.3369(15) . ?
N1 C1 1.3397(15) . ?
C1 C5 1.3865(17) . ?
C2 C3 1.3886(17) . ?
C3 C4 1.3884(17) . ?
C4 C5 1.3871(18) . ?
C6 C7 1.5072(17) . ?
C7 C11 1.4031(18) . ?
C8 C9 1.3985(17) . ?
C8 C13 1.5064(17) . ?
C9 C10 1.3985(17) . ?
C10 C14 1.5074(17) . ?
C11 C12 1.3947(18) . ?
C12 C15 1.5084(17) . ?
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
C3 H3 O4 0.95 2.52 3.4609(15) 172.5 2_667 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
_geom_torsion_publ_flag
C2 N1 C1 C5 -0.13(18) . . . . ?
Cu1 N1 C1 C5 178.28(10) . . . . ?
C1 N1 C2 C3 -0.94(18) . . . . ?
Cu1 N1 C2 C3 -179.44(9) . . . . ?
N1 C2 C3 C4 1.13(19) . . . . ?
C2 C3 C4 C5 -0.26(19) . . . . ?
N1 C1 C5 C4 0.9(2) . . . . ?
C3 C4 C5 C1 -0.7(2) . . . . ?
Cu1 O1 C7 C11 -11.20(18) . . . . ?
Cu1 O1 C7 C6 169.37(9) . . . . ?
Cu1 O2 C8 C9 10.19(18) . . . . ?
Cu1 O2 C8 C13 -171.37(9) . . . . ?
O2 C8 C9 C10 6.0(2) . . . . ?
C13 C8 C9 C10 -172.41(12) . . . . ?
Cu1 O3 C10 C9 -11.33(17) . . . . ?
Cu1 O3 C10 C14 170.30(9) . . . . ?
C8 C9 C10 O3 -5.3(2) . . . . ?
C8 C9 C10 C14 173.06(12) . . . . ?
O1 C7 C11 C12 -5.4(2) . . . . ?
C6 C7 C11 C12 174.00(12) . . . . ?
Cu1 O4 C12 C11 12.85(17) . . . . ?
Cu1 O4 C12 C15 -167.97(8) . . . . ?
C7 C11 C12 O4 4.5(2) . . . . ?
C7 C11 C12 C15 -174.70(12) . . . . ?
