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#$Date: 2025-08-06 07:40:01 +0200 (Wed 06 de Aug de 2025) $
#$Revision: 301657 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/53/1575326.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_1575326
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            'C19 H26 Cu N2 O4'
_chemical_formula_weight         409.96
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'intrinsic phasing'
_audit_creation_method           SHELXL-2019/1
_cell_angle_alpha                90
_cell_angle_beta                 107.4790(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9402(3)
_cell_length_b                   12.2115(3)
_cell_length_c                   15.0631(4)
_cell_measurement_reflns_used    7407
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.685
_cell_measurement_theta_min      2.568
_cell_volume                     1919.46(9)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0305
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14383
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.707
_diffrn_reflns_theta_min         2.567
_diffrn_source                   Microsource
_exptl_absorpt_coefficient_mu    1.164
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6904
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       block
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.094
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.042
_refine_diff_density_max         2.116
_refine_diff_density_min         -0.733
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         2482
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0300P)²+5.0669P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0826
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2284
_reflns_number_total             2482
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            Compound_3.cif
_cod_data_source_block           sad_a
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1575326
_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.500000 0.43548(3) 0.750000 0.01337(10) Uani 1 2 d S T P . .
O1 O 0.57023(12) 0.39432(11) 0.64834(9) 0.0161(3) Uani 1 1 d . . . . .
O2 O 0.32636(12) 0.42890(11) 0.66915(9) 0.0163(3) Uani 1 1 d . . . . .
N1 N 0.500000 0.61615(18) 0.750000 0.0148(4) Uani 1 2 d S T P . .
N2 N 0.500000 0.95887(18) 0.750000 0.0168(4) Uani 1 2 d S T P . .
C1 C 0.5803(2) 0.33190(19) 0.50240(15) 0.0256(4) Uani 1 1 d . . . . .
H1A H 0.523355 0.327764 0.438352 0.038 Uiso 1 1 calc R U . . .
H1B H 0.616850 0.259427 0.522176 0.038 Uiso 1 1 calc R U . . .
H1C H 0.649531 0.384039 0.505446 0.038 Uiso 1 1 calc R U . . .
C2 C 0.50494(18) 0.36965(15) 0.56600(13) 0.0168(4) Uani 1 1 d . . . . .
C3 C 0.29055(17) 0.40486(15) 0.58332(13) 0.0159(4) Uani 1 1 d . . . . .
C4 C 0.37056(19) 0.37364(17) 0.53107(14) 0.0210(4) Uani 1 1 d . . . . .
H4 H 0.331787 0.353821 0.467862 0.025 Uiso 1 1 calc R U . . .
C5 C 0.14784(19) 0.41421(19) 0.53687(15) 0.0252(4) Uani 1 1 d . . . . .
H5A H 0.124664 0.374674 0.477524 0.038 Uiso 1 1 calc R U . . .
H5B H 0.124407 0.491544 0.525537 0.038 Uiso 1 1 calc R U . . .
H5C H 0.101914 0.382480 0.577437 0.038 Uiso 1 1 calc R U . . .
C6 C 0.60898(17) 0.67482(15) 0.77340(13) 0.0153(3) Uani 1 1 d . . . . .
H6 H 0.687596 0.635585 0.790325 0.018 Uiso 1 1 calc R U . . .
C7 C 0.61538(17) 0.78737(15) 0.77470(13) 0.0150(3) Uani 1 1 d . . . . .
H7 H 0.695967 0.823564 0.791902 0.018 Uiso 1 1 calc R U . . .
C8 C 0.500000 0.8484(2) 0.750000 0.0134(5) Uani 1 2 d S T P . .
C9 C 0.61696(18) 1.02510(15) 0.77704(14) 0.0172(4) Uani 1 1 d . . . . .
H9A H 0.678611 1.000077 0.744842 0.021 Uiso 1 1 calc R U . . .
H9B H 0.658637 1.022166 0.845125 0.021 Uiso 1 1 calc R U . . .
C10 C 0.56843(19) 1.14014(16) 0.74605(17) 0.0235(4) Uani 1 1 d . . . . .
H10A H 0.567904 1.154116 0.681195 0.028 Uiso 1 1 calc R U . . .
H10B H 0.622081 1.196237 0.787255 0.028 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 O2 175.22(8) . 2_656 ?
O2 Cu1 O1 92.22(5) . . ?
O2 Cu1 O1 86.57(6) 2_656 . ?
O2 Cu1 O1 86.57(6) . 2_656 ?
O2 Cu1 O1 92.22(5) 2_656 2_656 ?
O1 Cu1 O1 150.49(8) . 2_656 ?
O2 Cu1 N1 92.39(4) . . ?
O2 Cu1 N1 92.39(4) 2_656 . ?
O1 Cu1 N1 104.75(4) . . ?
O1 Cu1 N1 104.75(4) 2_656 . ?
C2 O1 Cu1 125.69(12) . . ?
C3 O2 Cu1 126.77(12) . . ?
C6 N1 C6 115.6(2) 2_656 . ?
C6 N1 Cu1 122.21(11) 2_656 . ?
C6 N1 Cu1 122.21(11) . . ?
C8 N2 C9 123.53(10) . . ?
C8 N2 C9 123.53(10) . 2_656 ?
C9 N2 C9 112.9(2) . 2_656 ?
O1 C2 C4 125.20(17) . . ?
O1 C2 C1 116.00(17) . . ?
C4 C2 C1 118.79(17) . . ?
O2 C3 C4 125.79(17) . . ?
O2 C3 C5 114.49(17) . . ?
C4 C3 C5 119.72(17) . . ?
C3 C4 C2 124.16(18) . . ?
N1 C6 C7 124.99(18) . . ?
C6 C7 C8 118.99(17) . . ?
N2 C8 C7 121.77(11) . . ?
N2 C8 C7 121.77(11) . 2_656 ?
C7 C8 C7 116.5(2) . 2_656 ?
N2 C9 C10 103.24(15) . . ?
C9 C10 C10 103.53(12) . 2_656 ?
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 1.9257(13) . ?
Cu1 O2 1.9257(13) 2_656 ?
Cu1 O1 1.9735(13) . ?
Cu1 O1 1.9736(13) 2_656 ?
Cu1 N1 2.206(2) . ?
O1 C2 1.268(2) . ?
O2 C3 1.268(2) . ?
N1 C6 1.344(2) 2_656 ?
N1 C6 1.344(2) . ?
N2 C8 1.349(3) . ?
N2 C9 1.464(2) . ?
N2 C9 1.464(2) 2_656 ?
C1 C2 1.511(3) . ?
C2 C4 1.406(3) . ?
C3 C4 1.395(3) . ?
C3 C5 1.511(3) . ?
C6 C7 1.376(3) . ?
C7 C8 1.416(2) . ?
C9 C10 1.525(3) . ?
C10 C10 1.537(4) 2_656 ?
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
C6 H6 O2 0.95 2.61 3.146(2) 116.0 2_656 yes
C7 H7 O1 0.95 2.59 3.533(2) 171.2 4_656 yes
C9 H9A O2 0.99 2.40 3.392(2) 176.8 3 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
Cu1 O1 C2 C4 4.0(3) . . . . ?
Cu1 O1 C2 C1 -175.16(13) . . . . ?
Cu1 O2 C3 C4 2.9(3) . . . . ?
Cu1 O2 C3 C5 -175.97(13) . . . . ?
O2 C3 C4 C2 -3.3(3) . . . . ?
C5 C3 C4 C2 175.53(19) . . . . ?
O1 C2 C4 C3 -0.5(3) . . . . ?
C1 C2 C4 C3 178.66(19) . . . . ?
C6 N1 C6 C7 -0.06(14) 2_656 . . . ?
Cu1 N1 C6 C7 179.95(14) . . . . ?
N1 C6 C7 C8 0.1(3) . . . . ?
C9 N2 C8 C7 -1.42(13) . . . . ?
C9 N2 C8 C7 178.58(13) 2_656 . . . ?
C9 N2 C8 C7 178.58(13) . . . 2_656 ?
C9 N2 C8 C7 -1.42(13) 2_656 . . 2_656 ?
C6 C7 C8 N2 179.95(12) . . . . ?
C6 C7 C8 C7 -0.05(12) . . . 2_656 ?
C8 N2 C9 C10 168.43(10) . . . . ?
C9 N2 C9 C10 -11.58(10) 2_656 . . . ?
N2 C9 C10 C10 29.7(2) . . . 2_656 ?
