#------------------------------------------------------------------------------
#$Date: 2025-08-20 21:19:29 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301836 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/35/4303547.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_4303547
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 H28 N2 O8 Zn, 2(H2 O)'
_chemical_formula_sum            'C24 H32 N2 O10 Zn'
_chemical_formula_weight         573.89
_chemical_name_common            Zn(acacphNHCHO)2(H2O)4
_chemical_name_systematic
;
 Trans-diaquabis(3-(4-(Z-formamido)phenyl)-2,4-pentanedionato)zinc
 dihydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 114.60(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.442(5)
_cell_length_b                   9.637(4)
_cell_length_c                   11.947(5)
_cell_measurement_reflns_used    3304
_cell_measurement_temperature    110
_cell_measurement_theta_max      29.131
_cell_measurement_theta_min      2.546
_cell_volume                     1302.5(10)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0521
_diffrn_reflns_av_sigmaI/netI    0.0817
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6452
_diffrn_reflns_theta_full        29.14
_diffrn_reflns_theta_max         29.14
_diffrn_reflns_theta_min         2.78
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.001
_exptl_absorpt_correction_T_max  0.9424
_exptl_absorpt_correction_T_min  0.8840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.090
_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     169
_refine_ls_number_reflns         3476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0537
_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)+(0.0481P)²+1.4461P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1385
_reflns_number_gt                2204
_reflns_number_total             3476
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic900202e_si_001_7.cif
_cod_data_source_block           compound_13
_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/c'
_cod_database_code               4303547
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Zn1 Zn 1.0000 0.5000 0.5000 0.02676(17) Uani 1 2 d S . .
O1 O 0.86459(17) 0.5144(2) 0.55191(19) 0.0261(5) Uani 1 1 d . . .
O2 O 0.92063(18) 0.3286(2) 0.4055(2) 0.0327(6) Uani 1 1 d . . .
O3 O 0.1997(2) 0.4586(3) -0.0959(2) 0.0508(8) Uani 1 1 d . . .
O1W O 0.90154(18) 0.6335(2) 0.3401(2) 0.0328(6) Uani 1 1 d . . .
H1W H 0.8712 0.6055 0.2664 0.049 Uiso 1 1 d R . .
H2W H 0.9249 0.7123 0.3264 0.049 Uiso 1 1 d R . .
O2W O 0.0270(2) 0.3782(3) 0.2046(2) 0.0490(7) Uani 1 1 d . . .
H3W H 0.0594 0.4100 0.2778 0.073 Uiso 1 1 d R . .
H4W H -0.0373 0.4241 0.1739 0.073 Uiso 1 1 d R . .
N1 N 0.2324(2) 0.3292(3) 0.0754(2) 0.0311(6) Uani 1 1 d . . .
H1 H 0.1949 0.2769 0.1080 0.037 Uiso 1 1 d R . .
C1 C 0.6647(3) 0.5441(4) 0.5147(3) 0.0296(7) Uani 1 1 d . . .
H1A H 0.6996 0.6175 0.5760 0.036 Uiso 1 1 d R . .
H1B H 0.6299 0.4730 0.5482 0.036 Uiso 1 1 d R . .
H1C H 0.6030 0.5839 0.4401 0.036 Uiso 1 1 d R . .
C2 C 0.7587(3) 0.4790(3) 0.4833(3) 0.0240(7) Uani 1 1 d . . .
C3 C 0.7264(3) 0.3834(3) 0.3850(3) 0.0259(7) Uani 1 1 d . . .
C4 C 0.8092(3) 0.3087(4) 0.3565(3) 0.0299(8) Uani 1 1 d . . .
C5 C 0.7683(3) 0.1943(4) 0.2623(4) 0.0443(10) Uani 1 1 d . . .
H5A H 0.7502 0.2326 0.1804 0.053 Uiso 1 1 d R . .
H5B H 0.6971 0.1515 0.2629 0.053 Uiso 1 1 d R . .
H5C H 0.8306 0.1242 0.2825 0.053 Uiso 1 1 d R . .
C6 C 0.5976(2) 0.3643(3) 0.3031(3) 0.0240(7) Uani 1 1 d . . .
C7 C 0.5210(3) 0.2913(4) 0.3394(3) 0.0292(7) Uani 1 1 d . . .
H7 H 0.5512 0.2472 0.4176 0.035 Uiso 1 1 d R . .
C8 C 0.4011(3) 0.2813(3) 0.2630(3) 0.0283(7) Uani 1 1 d . . .
H8 H 0.3502 0.2309 0.2894 0.034 Uiso 1 1 d R . .
C9 C 0.3555(3) 0.3454(3) 0.1485(3) 0.0249(7) Uani 1 1 d . . .
C10 C 0.4300(3) 0.4166(4) 0.1103(3) 0.0323(8) Uani 1 1 d . . .
H10 H 0.3999 0.4604 0.0319 0.039 Uiso 1 1 d R . .
C11 C 0.5496(3) 0.4245(4) 0.1872(3) 0.0307(8) Uani 1 1 d . . .
H11 H 0.6005 0.4723 0.1592 0.037 Uiso 1 1 d R . .
C12 C 0.1656(3) 0.3826(4) -0.0349(3) 0.0369(9) Uani 1 1 d . . .
H12 H 0.0841 0.3587 -0.0698 0.044 Uiso 1 1 d 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'
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'
Zn Zn 0.2839 1.4301 '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 Zn1 O2 180.00(8) . 3_766 ?
O2 Zn1 O1 87.23(9) . . ?
O2 Zn1 O1 92.77(9) 3_766 . ?
O2 Zn1 O1 92.77(9) . 3_766 ?
O2 Zn1 O1 87.23(9) 3_766 3_766 ?
O1 Zn1 O1 180.0 . 3_766 ?
O2 Zn1 O1W 88.45(10) . 3_766 ?
O2 Zn1 O1W 91.55(10) 3_766 3_766 ?
O1 Zn1 O1W 90.44(9) . 3_766 ?
O1 Zn1 O1W 89.56(9) 3_766 3_766 ?
O2 Zn1 O1W 91.55(10) . . ?
O2 Zn1 O1W 88.45(10) 3_766 . ?
O1 Zn1 O1W 89.56(9) . . ?
O1 Zn1 O1W 90.44(9) 3_766 . ?
O1W Zn1 O1W 180.0 3_766 . ?
C2 O1 Zn1 123.6(2) . . ?
C4 O2 Zn1 124.5(2) . . ?
Zn1 O1W H1W 124.2 . . ?
Zn1 O1W H2W 125.1 . . ?
H1W O1W H2W 97.2 . . ?
H3W O2W H4W 102.3 . . ?
C12 N1 C9 129.3(3) . . ?
C12 N1 H1 115.5 . . ?
C9 N1 H1 115.2 . . ?
C2 C1 H1A 109.8 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.4 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 124.7(3) . . ?
O1 C2 C1 115.5(3) . . ?
C3 C2 C1 119.8(3) . . ?
C4 C3 C2 123.4(3) . . ?
C4 C3 C6 118.0(3) . . ?
C2 C3 C6 118.6(3) . . ?
O2 C4 C3 125.2(3) . . ?
O2 C4 C5 114.7(3) . . ?
C3 C4 C5 120.0(3) . . ?
C4 C5 H5A 109.7 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C6 C7 117.2(3) . . ?
C11 C6 C3 119.9(3) . . ?
C7 C6 C3 122.8(3) . . ?
C8 C7 C6 121.1(3) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.4 . . ?
C9 C8 C7 120.2(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 119.6(3) . . ?
C10 C9 N1 123.6(3) . . ?
C8 C9 N1 116.8(3) . . ?
C9 C10 C11 119.5(3) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.2 . . ?
C6 C11 C10 122.4(3) . . ?
C6 C11 H11 118.8 . . ?
C10 C11 H11 118.7 . . ?
O3 C12 N1 126.1(3) . . ?
O3 C12 H12 117.0 . . ?
N1 C12 H12 116.9 . . ?
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
Zn1 O2 2.012(2) . ?
Zn1 O2 2.012(2) 3_766 ?
Zn1 O1 2.028(2) . ?
Zn1 O1 2.028(2) 3_766 ?
Zn1 O1W 2.204(2) 3_766 ?
Zn1 O1W 2.204(2) . ?
O1 C2 1.275(4) . ?
O2 C4 1.275(4) . ?
O3 C12 1.226(4) . ?
O1W H1W 0.8449 . ?
O1W H2W 0.8530 . ?
O2W H3W 0.8537 . ?
O2W H4W 0.8517 . ?
N1 C12 1.335(4) . ?
N1 C9 1.421(4) . ?
N1 H1 0.8801 . ?
C1 C2 1.506(4) . ?
C1 H1A 0.9799 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9799 . ?
C2 C3 1.413(4) . ?
C3 C4 1.409(4) . ?
C3 C6 1.501(4) . ?
C4 C5 1.505(5) . ?
C5 H5A 0.9801 . ?
C5 H5B 0.9799 . ?
C5 H5C 0.9801 . ?
C6 C11 1.385(4) . ?
C6 C7 1.391(4) . ?
C7 C8 1.391(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.376(4) . ?
C10 C11 1.388(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9499 . ?
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 O1W 0.88 2.09 2.959(4) 170.8 2_645
O1W H1W O3 0.84 1.95 2.797(4) 179.7 3_665
O1W H2W O2W 0.85 1.80 2.651(4) 179.3 2_655
O2W H3W O1 0.85 1.99 2.844(3) 179.6 3_666
O2W H4W O3 0.85 2.16 3.011(4) 179.7 3_565
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 Zn1 O1 C2 -34.2(2) . . . . ?
O2 Zn1 O1 C2 145.8(2) 3_766 . . . ?
O1W Zn1 O1 C2 -122.6(2) 3_766 . . . ?
O1W Zn1 O1 C2 57.4(2) . . . . ?
O1 Zn1 O2 C4 31.0(3) . . . . ?
O1 Zn1 O2 C4 -149.0(3) 3_766 . . . ?
O1W Zn1 O2 C4 121.6(3) 3_766 . . . ?
O1W Zn1 O2 C4 -58.4(3) . . . . ?
Zn1 O1 C2 C3 23.4(4) . . . . ?
Zn1 O1 C2 C1 -157.9(2) . . . . ?
O1 C2 C3 C4 4.4(5) . . . . ?
C1 C2 C3 C4 -174.2(3) . . . . ?
O1 C2 C3 C6 -173.0(3) . . . . ?
C1 C2 C3 C6 8.4(4) . . . . ?
Zn1 O2 C4 C3 -16.8(5) . . . . ?
Zn1 O2 C4 C5 163.7(2) . . . . ?
C2 C3 C4 O2 -8.2(6) . . . . ?
C6 C3 C4 O2 169.2(3) . . . . ?
C2 C3 C4 C5 171.2(3) . . . . ?
C6 C3 C4 C5 -11.4(5) . . . . ?
C4 C3 C6 C11 -74.3(4) . . . . ?
C2 C3 C6 C11 103.2(4) . . . . ?
C4 C3 C6 C7 107.8(4) . . . . ?
C2 C3 C6 C7 -74.7(4) . . . . ?
C11 C6 C7 C8 -1.0(5) . . . . ?
C3 C6 C7 C8 177.0(3) . . . . ?
C6 C7 C8 C9 -0.3(5) . . . . ?
C7 C8 C9 C10 1.1(5) . . . . ?
C7 C8 C9 N1 179.4(3) . . . . ?
C12 N1 C9 C10 -4.4(6) . . . . ?
C12 N1 C9 C8 177.5(3) . . . . ?
C8 C9 C10 C11 -0.6(5) . . . . ?
N1 C9 C10 C11 -178.7(3) . . . . ?
C7 C6 C11 C10 1.6(5) . . . . ?
C3 C6 C11 C10 -176.5(3) . . . . ?
C9 C10 C11 C6 -0.8(6) . . . . ?
C9 N1 C12 O3 0.0(6) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168336821
