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#$Date: 2025-08-06 08:43:02 +0300 (Wed, 06 Aug 2025) $
#$Revision: 301664 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/53/1575333.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_1575333
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            'C16 H21 Cu N O4'
_chemical_formula_weight         354.88
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 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                 116.6270(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.7043(4)
_cell_length_b                   9.5368(2)
_cell_length_c                   17.9698(4)
_cell_measurement_reflns_used    9990
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.01
_cell_measurement_theta_min      2.380
_cell_volume                     3325.08(12)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0190
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            29205
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.057
_diffrn_reflns_theta_min         1.905
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    1.330
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6729
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       block
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         5151
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0241
_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)+(0.0402P)²+2.8763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0743
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4783
_reflns_number_total             5151
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            Compound_2.cif
_cod_data_source_block           sad_b
_cod_original_cell_volume        3325.07(12)
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               1575333
_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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 0.70939(2) 0.500000 0.18772(2) 0.01509(6) Uani 1 2 d S T P . .
Cu2 Cu 0.54564(2) 0.500000 0.31399(2) 0.01793(6) Uani 1 2 d S T P . .
O1 O 0.69109(4) 0.35310(9) 0.10559(5) 0.02152(16) Uani 1 1 d . . . . .
O2 O 0.71267(4) 0.64706(8) 0.26364(5) 0.01913(15) Uani 1 1 d . . . . .
O3 O 0.56615(4) 0.64788(9) 0.39651(5) 0.02267(16) Uani 1 1 d . . . . .
O4 O 0.54373(4) 0.64826(9) 0.23866(5) 0.02214(16) Uani 1 1 d . . . . .
N1 N 0.82616(6) 0.500000 0.23164(8) 0.0158(2) Uani 1 2 d S T P . .
N2 N 0.43115(7) 0.500000 0.27197(8) 0.0185(2) Uani 1 2 d S T P . .
C1 C 0.96966(7) 0.500000 0.28623(10) 0.0171(3) Uani 1 2 d S T P . .
C2 C 0.94122(8) 0.500000 0.34207(9) 0.0187(3) Uani 1 2 d S T P . .
H2 H 0.970486 0.500000 0.400297 0.022 Uiso 1 2 calc R U P . .
C3 C 0.87037(7) 0.500000 0.31273(9) 0.0175(3) Uani 1 2 d S T P . .
H3 H 0.852262 0.500000 0.352042 0.021 Uiso 1 2 calc R U P . .
C4 C 0.85326(8) 0.500000 0.17768(9) 0.0184(3) Uani 1 2 d S T P . .
H4 H 0.822731 0.500000 0.119827 0.022 Uiso 1 2 calc R U P . .
C5 C 0.92342(8) 0.500000 0.20198(10) 0.0188(3) Uani 1 2 d S T P . .
H5 H 0.940015 0.500000 0.161227 0.023 Uiso 1 2 calc R U P . .
C6 C 1.04606(8) 0.500000 0.31573(12) 0.0265(3) Uani 1 2 d S T P . .
H6A H 1.068215 0.556869 0.366334 0.040 Uiso 0.5 1 calc R U P . .
H6B H 1.056540 0.539493 0.272338 0.040 Uiso 0.5 1 calc R U P . .
H6C H 1.063430 0.403638 0.327811 0.040 Uiso 0.5 1 calc R U P . .
C7 C 0.65727(9) 0.23757(18) -0.02224(10) 0.0408(3) Uani 1 1 d . . . . .
H7A H 0.642301 0.260953 -0.080927 0.061 Uiso 1 1 calc R U . . .
H7B H 0.620990 0.184049 -0.016727 0.061 Uiso 1 1 calc R U . . .
H7C H 0.699444 0.181182 -0.001703 0.061 Uiso 1 1 calc R U . . .
C8 C 0.67127(6) 0.37086(14) 0.02805(7) 0.0248(2) Uani 1 1 d . . . . .
C9 C 0.71072(5) 0.62971(12) 0.33285(7) 0.01905(19) Uani 1 1 d . . . . .
C10 C 0.71078(8) 0.500000 0.36934(10) 0.0222(3) Uani 1 2 d S T P . .
H10 H 0.710853 0.499999 0.422250 0.027 Uiso 1 2 calc R U P . .
C11 C 0.66169(10) 0.500000 -0.01200(11) 0.0316(4) Uani 1 2 d S T P . .
H11 H 0.647766 0.500002 -0.070223 0.038 Uiso 1 2 calc R U P . .
C12 C 0.70655(6) 0.76286(14) 0.37542(8) 0.0272(2) Uani 1 1 d . . . . .
H12A H 0.709251 0.740333 0.430011 0.041 Uiso 1 1 calc R U . . .
H12B H 0.662774 0.810242 0.341320 0.041 Uiso 1 1 calc R U . . .
H12C H 0.744898 0.824666 0.382624 0.041 Uiso 1 1 calc R U . . .
C13 C 0.60070(8) 0.76179(15) 0.52512(9) 0.0337(3) Uani 1 1 d . . . . .
H13A H 0.619262 0.737568 0.584228 0.051 Uiso 1 1 calc R U . . .
H13B H 0.557370 0.813339 0.507731 0.051 Uiso 1 1 calc R U . . .
H13C H 0.633976 0.820452 0.516405 0.051 Uiso 1 1 calc R U . . .
C14 C 0.58762(6) 0.62951(13) 0.47433(7) 0.0226(2) Uani 1 1 d . . . . .
C15 C 0.54600(5) 0.62974(13) 0.16979(7) 0.0218(2) Uani 1 1 d . . . . .
C16 C 0.54710(8) 0.500000 0.13430(10) 0.0244(3) Uani 1 2 d S T P . .
H16 H 0.548704 0.500002 0.082334 0.029 Uiso 1 2 calc R U P . .
C17 C 0.59991(10) 0.500000 0.51485(11) 0.0271(3) Uani 1 2 d S T P . .
H17 H 0.617770 0.499999 0.573745 0.033 Uiso 1 2 calc R U P . .
C18 C 0.54927(7) 0.76219(15) 0.12571(8) 0.0301(3) Uani 1 1 d . . . . .
H18A H 0.546653 0.738292 0.071332 0.045 Uiso 1 1 calc R U . . .
H18B H 0.592736 0.810996 0.159259 0.045 Uiso 1 1 calc R U . . .
H18C H 0.510529 0.823280 0.117924 0.045 Uiso 1 1 calc R U . . .
C19 C 0.21183(9) 0.500000 0.18815(13) 0.0302(4) Uani 1 2 d S T P . .
H19A H 0.195116 0.596880 0.181306 0.045 Uiso 0.5 1 calc R U P . .
H19B H 0.201144 0.452251 0.229259 0.045 Uiso 0.5 1 calc R U P . .
H19C H 0.189258 0.450869 0.134701 0.045 Uiso 0.5 1 calc R U P . .
C20 C 0.28825(8) 0.500000 0.21750(10) 0.0195(3) Uani 1 2 d S T P . .
C21 C 0.32504(6) 0.37528(11) 0.23165(8) 0.0227(2) Uani 1 1 d . . . . .
H21 H 0.302030 0.287633 0.222953 0.027 Uiso 1 1 calc R U . . .
C22 C 0.39570(6) 0.38041(11) 0.25860(7) 0.0220(2) Uani 1 1 d . . . . .
H22 H 0.420162 0.294415 0.268044 0.026 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'
N N 0.0061 0.0033 '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'
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 92.87(5) 6_565 . ?
O2 Cu1 O1 171.32(3) 6_565 6_565 ?
O2 Cu1 O1 86.75(4) . 6_565 ?
O2 Cu1 O1 86.75(4) 6_565 . ?
O2 Cu1 O1 171.33(3) . . ?
O1 Cu1 O1 92.31(5) 6_565 . ?
O2 Cu1 N1 94.10(3) 6_565 . ?
O2 Cu1 N1 94.11(3) . . ?
O1 Cu1 N1 94.57(3) 6_565 . ?
O1 Cu1 N1 94.57(3) . . ?
O4 Cu2 O4 93.26(5) . 6_565 ?
O4 Cu2 O3 85.98(4) . . ?
O4 Cu2 O3 169.26(4) 6_565 . ?
O4 Cu2 O3 169.26(4) . 6_565 ?
O4 Cu2 O3 85.98(4) 6_565 6_565 ?
O3 Cu2 O3 92.77(5) . 6_565 ?
O4 Cu2 N2 95.20(3) . . ?
O4 Cu2 N2 95.20(3) 6_565 . ?
O3 Cu2 N2 95.54(3) . . ?
O3 Cu2 N2 95.54(3) 6_565 . ?
C8 O1 Cu1 126.14(8) . . ?
C9 O2 Cu1 125.96(8) . . ?
C14 O3 Cu2 125.67(8) . . ?
C15 O4 Cu2 125.30(8) . . ?
C3 N1 C4 117.03(13) . . ?
C3 N1 Cu1 121.17(10) . . ?
C4 N1 Cu1 121.79(10) . . ?
C22 N2 C22 117.23(13) 6_565 . ?
C22 N2 Cu2 121.38(7) 6_565 . ?
C22 N2 Cu2 121.38(7) . . ?
C5 C1 C2 116.54(13) . . ?
C5 C1 C6 121.96(14) . . ?
C2 C1 C6 121.50(14) . . ?
C3 C2 C1 120.04(14) . . ?
N1 C3 C2 123.15(14) . . ?
N1 C4 C5 123.33(14) . . ?
C4 C5 C1 119.90(14) . . ?
O1 C8 C11 125.60(12) . . ?
O1 C8 C7 114.97(12) . . ?
C11 C8 C7 119.43(12) . . ?
O2 C9 C10 125.36(11) . . ?
O2 C9 C12 114.97(11) . . ?
C10 C9 C12 119.66(10) . . ?
C9 C10 C9 124.18(14) . 6_565 ?
C8 C11 C8 124.09(16) . 6_565 ?
O3 C14 C17 125.78(12) . . ?
O3 C14 C13 115.27(11) . . ?
C17 C14 C13 118.94(11) . . ?
O4 C15 C16 125.65(12) . . ?
O4 C15 C18 115.19(11) . . ?
C16 C15 C18 119.15(11) . . ?
C15 C16 C15 124.66(15) . 6_565 ?
C14 C17 C14 124.22(15) 6_565 . ?
C21 C20 C21 117.53(14) 6_565 . ?
C21 C20 C19 121.23(7) 6_565 . ?
C21 C20 C19 121.23(7) . . ?
C22 C21 C20 119.21(11) . . ?
N2 C22 C21 123.40(10) . . ?
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 1.9355(8) 6_565 ?
Cu1 O2 1.9355(8) . ?
Cu1 O1 1.9425(8) 6_565 ?
Cu1 O1 1.9425(8) . ?
Cu1 N1 2.2920(12) . ?
Cu2 O4 1.9451(8) . ?
Cu2 O4 1.9451(8) 6_565 ?
Cu2 O3 1.9480(8) . ?
Cu2 O3 1.9480(8) 6_565 ?
Cu2 N2 2.2502(13) . ?
O1 C8 1.2720(14) . ?
O2 C9 1.2739(13) . ?
O3 C14 1.2724(14) . ?
O4 C15 1.2725(13) . ?
N1 C3 1.3381(19) . ?
N1 C4 1.3407(19) . ?
N2 C22 1.3360(13) 6_565 ?
N2 C22 1.3360(13) . ?
C1 C5 1.392(2) . ?
C1 C2 1.394(2) . ?
C1 C6 1.498(2) . ?
C2 C3 1.384(2) . ?
C4 C5 1.383(2) . ?
C7 C8 1.5095(19) . ?
C8 C11 1.3942(16) . ?
C9 C10 1.3998(14) . ?
C9 C12 1.5060(16) . ?
C13 C14 1.5075(17) . ?
C14 C17 1.3975(15) . ?
C15 C16 1.3971(15) . ?
C15 C18 1.5095(17) . ?
C19 C20 1.498(2) . ?
C20 C21 1.3910(13) 6_565 ?
C20 C21 1.3910(13) . ?
C21 C22 1.3868(15) . ?
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
C5 C1 C2 C3 0.000(0) . . . . ?
C6 C1 C2 C3 180.000(0) . . . . ?
C4 N1 C3 C2 0.000(0) . . . . ?
Cu1 N1 C3 C2 180.000(0) . . . . ?
C1 C2 C3 N1 0.000(0) . . . . ?
C3 N1 C4 C5 0.000(0) . . . . ?
Cu1 N1 C4 C5 180.000(0) . . . . ?
N1 C4 C5 C1 0.000(0) . . . . ?
C2 C1 C5 C4 0.000(0) . . . . ?
C6 C1 C5 C4 180.000(0) . . . . ?
Cu1 O1 C8 C11 2.83(19) . . . . ?
Cu1 O1 C8 C7 -176.86(9) . . . . ?
Cu1 O2 C9 C10 4.83(16) . . . . ?
Cu1 O2 C9 C12 -173.83(7) . . . . ?
O2 C9 C10 C9 -2.2(2) . . . 6_565 ?
C12 C9 C10 C9 176.40(10) . . . 6_565 ?
O1 C8 C11 C8 -1.5(3) . . . 6_565 ?
C7 C8 C11 C8 178.17(14) . . . 6_565 ?
Cu2 O3 C14 C17 -0.56(18) . . . . ?
Cu2 O3 C14 C13 179.08(8) . . . . ?
Cu2 O4 C15 C16 3.09(16) . . . . ?
Cu2 O4 C15 C18 -175.53(7) . . . . ?
O4 C15 C16 C15 -0.1(2) . . . 6_565 ?
C18 C15 C16 C15 178.42(11) . . . 6_565 ?
O3 C14 C17 C14 -2.6(3) . . . 6_565 ?
C13 C14 C17 C14 177.82(13) . . . 6_565 ?
C21 C20 C21 C22 -0.2(2) 6_565 . . . ?
C19 C20 C21 C22 179.84(14) . . . . ?
C22 N2 C22 C21 0.3(2) 6_565 . . . ?
Cu2 N2 C22 C21 -179.12(10) . . . . ?
C20 C21 C22 N2 0.0(2) . . . . ?
