#------------------------------------------------------------------------------
#$Date: 2025-08-20 21:19:29 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301836 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/35/4303546.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_4303546
loop_
_publ_author_name
'Yixun Zhang'
'Andrew W. Maverick'
_publ_section_title
;
Preparation of an Isocyano-β-diketone via its Metal Complexes, by Use of
Metal Ions as Protecting Groups
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              10512
_journal_page_last               10518
_journal_paper_doi               10.1021/ic900202e
_journal_volume                  48
_journal_year                    2009
_chemical_compound_source        'Local laboratory'
_chemical_formula_moiety         'C24 H24 Cu N2 O6'
_chemical_formula_sum            'C24 H24 Cu N2 O6'
_chemical_formula_weight         500.00
_chemical_name_common            Cu(acphNHCHO)2
_chemical_name_systematic
;
 Bis(3-(4-(Z-formamido)phenyl)-2,4-pentanedionato)copper
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.166(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.136(2)
_cell_length_b                   7.480(2)
_cell_length_c                   17.771(4)
_cell_measurement_reflns_used    2679
_cell_measurement_temperature    110
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      2.546
_cell_volume                     1053.1(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare  et al., 1999)'
_diffrn_ambient_temperature      110
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'KappaCCD (with Oxford Cryostream)'
_diffrn_measurement_method       ' ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_sigmaI/netI    0.0851
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            4860
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.57
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.084
_exptl_absorpt_correction_T_max  0.9787
_exptl_absorpt_correction_T_min  0.8808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor 1997)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             518
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         3048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0543
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0600P)²+0.8909P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1385
_reflns_number_gt                1984
_reflns_number_total             3048
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic900202e_si_001_6.cif
_cod_data_source_block           compound_12
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4303546
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.0000 0.0000 0.0000 0.01838(16) Uani 1 2 d S . .
O1 O 0.9859(3) 0.2353(3) 0.04073(13) 0.0199(5) Uani 1 1 d . . .
O2 O 0.8062(3) -0.0769(3) 0.03644(12) 0.0178(5) Uani 1 1 d . . .
O3 O 0.3055(3) 0.3990(3) 0.35255(13) 0.0253(5) Uani 1 1 d . . .
N1 N 0.3116(3) 0.5812(3) 0.25022(15) 0.0200(6) Uani 1 1 d . . .
H1 H 0.2725 0.6828 0.2283 0.024 Uiso 1 1 calc R . .
C1 C 0.9026(4) 0.4893(4) 0.09960(19) 0.0220(6) Uani 1 1 d . . .
H1A H 0.9936 0.4977 0.1463 0.033 Uiso 1 1 calc R . .
H1B H 0.7982 0.5372 0.1103 0.033 Uiso 1 1 calc R . .
H1C H 0.9331 0.5586 0.0580 0.033 Uiso 1 1 calc R . .
C2 C 0.8765(4) 0.2961(4) 0.07528(16) 0.0168(6) Uani 1 1 d . . .
C3 C 0.7425(4) 0.1973(4) 0.09258(17) 0.0157(6) Uani 1 1 d . . .
C4 C 0.7173(4) 0.0145(4) 0.07267(16) 0.0166(6) Uani 1 1 d . . .
C5 C 0.5754(4) -0.0854(4) 0.09623(18) 0.0201(6) Uani 1 1 d . . .
H5A H 0.5721 -0.2087 0.0773 0.030 Uiso 1 1 calc R . .
H5B H 0.4679 -0.0263 0.0740 0.030 Uiso 1 1 calc R . .
H5C H 0.5944 -0.0860 0.1527 0.030 Uiso 1 1 calc R . .
C6 C 0.6240(4) 0.2878(4) 0.13377(17) 0.0155(6) Uani 1 1 d . . .
C7 C 0.6485(4) 0.2783(4) 0.21434(17) 0.0180(6) Uani 1 1 d . . .
H7 H 0.7375 0.2065 0.2428 0.022 Uiso 1 1 calc R . .
C8 C 0.5463(4) 0.3710(4) 0.25381(17) 0.0175(6) Uani 1 1 d . . .
H8 H 0.5652 0.3623 0.3084 0.021 Uiso 1 1 calc R . .
C9 C 0.4155(4) 0.4771(4) 0.21238(18) 0.0177(6) Uani 1 1 d . . .
C10 C 0.3852(4) 0.4850(4) 0.13209(17) 0.0199(6) Uani 1 1 d . . .
H10 H 0.2949 0.5551 0.1036 0.024 Uiso 1 1 calc R . .
C11 C 0.4885(4) 0.3894(4) 0.09421(18) 0.0206(6) Uani 1 1 d . . .
H11 H 0.4657 0.3934 0.0394 0.025 Uiso 1 1 calc R . .
C12 C 0.2680(4) 0.5372(4) 0.31691(18) 0.0207(7) Uani 1 1 d . . .
H12 H 0.2026 0.6214 0.3376 0.025 Uiso 1 1 calc R . .
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
O1 Cu1 O1 180.00 . 3_755 ?
O1 Cu1 O2 91.35(8) . . ?
O1 Cu1 O2 88.65(8) 3_755 . ?
O1 Cu1 O2 88.65(8) . 3_755 ?
O1 Cu1 O2 91.35(8) 3_755 3_755 ?
O2 Cu1 O2 180.00 . 3_755 ?
O1 Cu1 O3 92.03(8) . 4_665 ?
O1 Cu1 O3 87.97(8) 3_755 4_665 ?
O2 Cu1 O3 93.61(8) . 4_665 ?
O2 Cu1 O3 86.39(8) 3_755 4_665 ?
O1 Cu1 O3 87.97(8) . 2_645 ?
O1 Cu1 O3 92.03(8) 3_755 2_645 ?
O2 Cu1 O3 86.39(8) . 2_645 ?
O2 Cu1 O3 93.61(8) 3_755 2_645 ?
O3 Cu1 O3 180.00 4_665 2_645 ?
C2 O1 Cu1 128.15(19) . . ?
C4 O2 Cu1 127.86(19) . . ?
C12 N1 C9 125.6(3) . . ?
C12 N1 H1 117.2 . . ?
C9 N1 H1 117.2 . . ?
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 125.3(3) . . ?
O1 C2 C1 114.3(3) . . ?
C3 C2 C1 120.4(3) . . ?
C2 C3 C4 121.8(3) . . ?
C2 C3 C6 119.1(2) . . ?
C4 C3 C6 119.1(3) . . ?
O2 C4 C3 125.4(3) . . ?
O2 C4 C5 115.6(2) . . ?
C3 C4 C5 119.0(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C6 C7 117.1(3) . . ?
C11 C6 C3 121.6(3) . . ?
C7 C6 C3 121.2(3) . . ?
C8 C7 C6 121.9(3) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C9 119.3(3) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 N1 118.3(3) . . ?
C8 C9 N1 121.6(3) . . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C6 122.3(3) . . ?
C10 C11 H11 118.9 . . ?
C6 C11 H11 118.9 . . ?
O3 C12 N1 125.4(3) . . ?
O3 C12 H12 117.3 . . ?
N1 C12 H12 117.3 . . ?
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 O1 1.9165(19) . ?
Cu1 O1 1.9165(19) 3_755 ?
Cu1 O2 1.924(2) . ?
Cu1 O2 1.924(2) 3_755 ?
Cu1 O3 2.838(2) 4_665 ?
Cu1 O3 2.838(2) 2_645 ?
O1 C2 1.275(4) . ?
O2 C4 1.272(4) . ?
O3 C12 1.215(4) . ?
N1 C12 1.353(4) . ?
N1 C9 1.426(4) . ?
N1 H1 0.8800 . ?
C1 C2 1.510(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.408(4) . ?
C3 C4 1.416(4) . ?
C3 C6 1.498(4) . ?
C4 C5 1.512(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C11 1.390(4) . ?
C6 C7 1.402(4) . ?
C7 C8 1.389(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.395(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.393(4) . ?
C10 C11 1.389(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
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
N1 H1 O3 0.88 2.16 3.017(3) 164.3 2
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
O2 Cu1 O1 C2 -1.9(3) . . . . ?
O2 Cu1 O1 C2 178.1(3) 3_755 . . . ?
O1 Cu1 O2 C4 0.4(2) . . . . ?
O1 Cu1 O2 C4 -179.6(2) 3_755 . . . ?
Cu1 O1 C2 C3 1.8(4) . . . . ?
Cu1 O1 C2 C1 -179.68(19) . . . . ?
O1 C2 C3 C4 0.3(5) . . . . ?
C1 C2 C3 C4 -178.1(3) . . . . ?
O1 C2 C3 C6 179.9(3) . . . . ?
C1 C2 C3 C6 1.4(4) . . . . ?
Cu1 O2 C4 C3 1.3(4) . . . . ?
Cu1 O2 C4 C5 -177.96(19) . . . . ?
C2 C3 C4 O2 -2.0(5) . . . . ?
C6 C3 C4 O2 178.5(3) . . . . ?
C2 C3 C4 C5 177.3(3) . . . . ?
C6 C3 C4 C5 -2.2(4) . . . . ?
C2 C3 C6 C11 83.2(4) . . . . ?
C4 C3 C6 C11 -97.2(3) . . . . ?
C2 C3 C6 C7 -94.6(3) . . . . ?
C4 C3 C6 C7 84.9(4) . . . . ?
C11 C6 C7 C8 -2.3(4) . . . . ?
C3 C6 C7 C8 175.7(3) . . . . ?
C6 C7 C8 C9 -0.1(4) . . . . ?
C7 C8 C9 C10 1.9(4) . . . . ?
C7 C8 C9 N1 -177.2(3) . . . . ?
C12 N1 C9 C10 148.6(3) . . . . ?
C12 N1 C9 C8 -32.3(5) . . . . ?
C8 C9 C10 C11 -1.3(4) . . . . ?
N1 C9 C10 C11 177.9(3) . . . . ?
C9 C10 C11 C6 -1.2(5) . . . . ?
C7 C6 C11 C10 2.9(4) . . . . ?
C3 C6 C11 C10 -175.0(3) . . . . ?
C9 N1 C12 O3 -3.2(5) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139127255
