#------------------------------------------------------------------------------
#$Date: 2025-08-20 21:19:29 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301836 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/35/4303543.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_4303543
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         'C12 H13 N O3'
_chemical_formula_sum            'C12 H13 N O3'
_chemical_formula_weight         219.23
_chemical_name_common            4-(Z-formamido)phenylacac
_chemical_name_systematic
;
 3-(4-(Z-formamido)phenyl)-2,4-pentanedione
;
_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                 111.153(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.289(2)
_cell_length_b                   7.5180(15)
_cell_length_c                   11.561(2)
_cell_measurement_reflns_used    2516
_cell_measurement_temperature    110
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.546
_cell_volume                     1077.2(3)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0434
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4649
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.17
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2468
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0424
_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)+(0.0572P)²+0.1446P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1109
_reflns_number_gt                1798
_reflns_number_total             2468
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic900202e_si_001_3.cif
_cod_data_source_block           compound_Z-2
_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               4303543
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
O1 O 0.46855(8) 0.65084(13) 0.40580(9) 0.0290(3) Uani 1 1 d . . .
O2 O 0.41601(8) 0.36355(14) 0.29668(10) 0.0304(3) Uani 1 1 d . . .
H2 H 0.4496(15) 0.457(3) 0.3614(18) 0.053(5) Uiso 1 1 d . . .
O3 O -0.12517(8) 0.82417(13) -0.25550(10) 0.0301(3) Uani 1 1 d . . .
N1 N 0.02198(9) 1.00858(15) -0.19461(10) 0.0235(3) Uani 1 1 d . . .
H1 H 0.0457 1.1095 -0.2137 0.028 Uiso 1 1 calc R . .
C1 C 0.38440(12) 0.9260(2) 0.32921(15) 0.0306(4) Uani 1 1 d . . .
H1A H 0.4117 0.9590 0.4171 0.046 Uiso 1 1 calc R . .
H1B H 0.3077 0.9569 0.2920 0.046 Uiso 1 1 calc R . .
H1C H 0.4248 0.9905 0.2864 0.046 Uiso 1 1 calc R . .
C2 C 0.39804(11) 0.72951(19) 0.31714(13) 0.0241(3) Uani 1 1 d . . .
C3 C 0.33188(11) 0.63342(18) 0.20813(13) 0.0222(3) Uani 1 1 d . . .
C4 C 0.34604(11) 0.45214(19) 0.20299(13) 0.0248(3) Uani 1 1 d . . .
C5 C 0.28771(10) 0.33518(11) 0.09537(8) 0.0297(4) Uani 1 1 d . . .
H5A H 0.3401 0.2649 0.0730 0.045 Uiso 1 1 calc R . .
H5B H 0.2453 0.4087 0.0246 0.045 Uiso 1 1 calc R . .
H5C H 0.2395 0.2551 0.1179 0.045 Uiso 1 1 calc R . .
C6 C 0.24975(7) 0.72940(11) 0.10321(8) 0.0214(3) Uani 1 1 d R . .
C7 C 0.28050(8) 0.84931(11) 0.03007(8) 0.0241(3) Uani 1 1 d R . .
H7 H 0.3551 0.8701 0.0478 0.029 Uiso 1 1 calc R . .
C8 C 0.20545(11) 0.93858(18) -0.06743(13) 0.0232(3) Uani 1 1 d . . .
H8 H 0.2287 1.0193 -0.1159 0.028 Uiso 1 1 calc R . .
C9 C 0.09585(11) 0.91039(17) -0.09477(13) 0.0212(3) Uani 1 1 d . . .
C10 C 0.06246(11) 0.79314(19) -0.02236(13) 0.0234(3) Uani 1 1 d . . .
H10 H -0.0122 0.7740 -0.0396 0.028 Uiso 1 1 calc R . .
C11 C 0.13927(11) 0.70454(18) 0.07523(13) 0.0231(3) Uani 1 1 d . . .
H11 H 0.1161 0.6248 0.1243 0.028 Uiso 1 1 calc R . .
C12 C -0.07995(12) 0.96393(19) -0.26269(14) 0.0257(3) Uani 1 1 d . . .
H12 H -0.1211 1.0484 -0.3221 0.031 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'
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
C4 O2 H2 104.5(11) . . ?
C12 N1 C9 126.99(12) . . ?
C12 N1 H1 116.5 . . ?
C9 N1 H1 116.5 . . ?
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 121.04(13) . . ?
O1 C2 C1 117.78(13) . . ?
C3 C2 C1 121.18(13) . . ?
C4 C3 C2 118.84(13) . . ?
C4 C3 C6 120.90(12) . . ?
C2 C3 C6 120.26(11) . . ?
O2 C4 C3 121.85(13) . . ?
O2 C4 C5 112.69(11) . . ?
C3 C4 C5 125.46(12) . . ?
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 . . ?
C7 C6 C11 117.36(7) . . ?
C7 C6 C3 121.13(6) . . ?
C11 C6 C3 121.51(10) . . ?
C8 C7 C6 121.75(7) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C9 120.03(12) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C10 119.62(13) . . ?
C8 C9 N1 117.70(12) . . ?
C10 C9 N1 122.65(12) . . ?
C11 C10 C9 119.44(12) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C6 121.80(12) . . ?
C10 C11 H11 119.1 . . ?
C6 C11 H11 119.1 . . ?
O3 C12 N1 126.15(13) . . ?
O3 C12 H12 116.9 . . ?
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
O1 C2 1.2591(17) . ?
O2 C4 1.3246(17) . ?
O2 H2 1.01(2) . ?
O3 C12 1.2281(17) . ?
N1 C12 1.3407(18) . ?
N1 C9 1.4224(17) . ?
N1 H1 0.8800 . ?
C1 C2 1.501(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.443(2) . ?
C3 C4 1.380(2) . ?
C3 C6 1.4926(16) . ?
C4 C5 1.4920(17) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.3944 . ?
C6 C11 1.3972(16) . ?
C7 C8 1.3800(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.3906(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.394(2) . ?
C10 C11 1.3883(19) . ?
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
O2 H2 O1 1.01(2) 1.54(2) 2.4714(15) 152.5(18) .
N1 H1 O3 0.88 2.03 2.9005(15) 170.5 2_554
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
O1 C2 C3 C4 0.9(2) . . . . ?
C1 C2 C3 C4 -178.51(13) . . . . ?
O1 C2 C3 C6 -179.16(11) . . . . ?
C1 C2 C3 C6 1.47(19) . . . . ?
C2 C3 C4 O2 2.2(2) . . . . ?
C6 C3 C4 O2 -177.79(11) . . . . ?
C2 C3 C4 C5 -177.29(13) . . . . ?
C6 C3 C4 C5 2.7(2) . . . . ?
C4 C3 C6 C7 -111.78(11) . . . . ?
C2 C3 C6 C7 68.24(13) . . . . ?
C4 C3 C6 C11 68.99(16) . . . . ?
C2 C3 C6 C11 -110.99(13) . . . . ?
C11 C6 C7 C8 -0.93(9) . . . . ?
C3 C6 C7 C8 179.81(12) . . . . ?
C6 C7 C8 C9 0.16(15) . . . . ?
C7 C8 C9 C10 0.7(2) . . . . ?
C7 C8 C9 N1 178.73(11) . . . . ?
C12 N1 C9 C8 155.85(14) . . . . ?
C12 N1 C9 C10 -26.2(2) . . . . ?
C8 C9 C10 C11 -0.7(2) . . . . ?
N1 C9 C10 C11 -178.68(12) . . . . ?
C9 C10 C11 C6 0.0(2) . . . . ?
C7 C6 C11 C10 0.87(15) . . . . ?
C3 C6 C11 C10 -179.88(12) . . . . ?
C9 N1 C12 O3 -4.9(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660752
2 PubChem 131519625
