#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/56/1515693.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_1515693
loop_
_publ_author_name
'Kawarada, Hikaru'
'Yoshikawa, Yutaka'
'Yasui, Hiroyuki'
'Kuwahara, Shunsuke'
'Habata, Yoichi'
'Saito, Ryota'
_publ_section_title
;
 Synthesis and in vitro insulin-mimetic activities of zinc(ii) complexes
 of ethyl 2,5-dihydro-4-hydroxy-5-oxo-1H-pyrrole-3-carboxylates.
;
_journal_issue                   7
_journal_name_full               'Metallomics : integrated biometal science'
_journal_page_first              675
_journal_page_last               679
_journal_paper_doi               10.1039/c1mt00009h
_journal_volume                  3
_journal_year                    2011
_chemical_formula_sum            'C28 H36 N2 O12 Zn'
_chemical_formula_weight         657.96
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8469(7)
_cell_length_b                   8.7118(5)
_cell_length_c                   28.9529(17)
_cell_measurement_temperature    100
_cell_volume                     2988.2(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            21051
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.41
_exptl_absorpt_coefficient_mu    0.888
_exptl_absorpt_correction_T_max  0.9048
_exptl_absorpt_correction_T_min  0.7974
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS, Sheldrick, 1996'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3713
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0626P)²+0.1653P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.1041
_reflns_number_gt                2920
_reflns_number_total             3713
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1mt00009h.txt
_cod_data_source_block           pbca
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1515693
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.18174(14) 0.35409(19) 0.65187(6) 0.0244(4) Uani 1 1 d .
H1A H 0.1189 0.3860 0.6315 0.029 Uiso 1 1 calc R
H1B H 0.2144 0.4479 0.6658 0.029 Uiso 1 1 calc R
C2 C 0.13550(14) 0.25288(19) 0.68993(6) 0.0224(3) Uani 1 1 d .
C3 C 0.03854(16) 0.1667(2) 0.68257(6) 0.0286(4) Uani 1 1 d .
H3 H 0.0008 0.1720 0.6537 0.034 Uiso 1 1 calc R
C4 C -0.00357(16) 0.0727(3) 0.71731(8) 0.0371(5) Uani 1 1 d .
H4 H -0.0695 0.0132 0.7120 0.045 Uiso 1 1 calc R
C5 C 0.0498(2) 0.0654(2) 0.75930(7) 0.0431(5) Uani 1 1 d .
H5 H 0.0209 0.0012 0.7830 0.052 Uiso 1 1 calc R
C6 C 0.1459(2) 0.1516(3) 0.76699(7) 0.0467(6) Uani 1 1 d .
H6 H 0.1826 0.1470 0.7961 0.056 Uiso 1 1 calc R
C7 C 0.18911(17) 0.2447(2) 0.73252(6) 0.0338(4) Uani 1 1 d .
H7 H 0.2555 0.3031 0.7380 0.041 Uiso 1 1 calc R
C8 C 0.38876(13) 0.30482(19) 0.62980(5) 0.0218(3) Uani 1 1 d .
H8A H 0.4148 0.2720 0.6608 0.026 Uiso 1 1 calc R
H8B H 0.4078 0.4144 0.6252 0.026 Uiso 1 1 calc R
C9 C 0.43912(13) 0.20668(18) 0.59252(5) 0.0194(3) Uani 1 1 d .
C10 C 0.35547(13) 0.13245(18) 0.56855(5) 0.0186(3) Uani 1 1 d .
C11 C 0.24467(13) 0.18150(19) 0.58922(5) 0.0191(3) Uani 1 1 d .
C12 C 0.55621(13) 0.20561(18) 0.58041(5) 0.0201(3) Uani 1 1 d .
C13 C 0.73804(13) 0.3105(2) 0.59487(6) 0.0251(4) Uani 1 1 d .
H13A H 0.7438 0.3682 0.5655 0.030 Uiso 1 1 calc R
H13B H 0.7741 0.2089 0.5907 0.030 Uiso 1 1 calc R
C14 C 0.79443(15) 0.3976(2) 0.63340(6) 0.0318(4) Uani 1 1 d .
H14A H 0.7550 0.4951 0.6383 0.048 Uiso 1 1 calc R
H14B H 0.8732 0.4180 0.6251 0.048 Uiso 1 1 calc R
H14C H 0.7918 0.3365 0.6618 0.048 Uiso 1 1 calc R
N1 N 0.26824(11) 0.27808(16) 0.62402(5) 0.0213(3) Uani 1 1 d .
O1 O 0.59757(9) 0.13411(14) 0.54751(4) 0.0230(3) Uani 1 1 d .
O2 O 0.35679(9) 0.03882(14) 0.53482(4) 0.0224(3) Uani 1 1 d .
O4 O 0.14944(9) 0.14061(14) 0.57656(4) 0.0232(3) Uani 1 1 d .
O5 O 0.62020(9) 0.29233(14) 0.60826(4) 0.0243(3) Uani 1 1 d .
O1S O 0.46962(11) 0.19859(15) 0.45964(4) 0.0245(3) Uani 1 1 d .
Zn1 Zn 0.5000 0.0000 0.5000 0.01935(10) Uani 1 2 d S
O2S O 0.34849(15) 0.4325(2) 0.49543(5) 0.0371(4) Uani 1 1 d .
H2X H 0.433(2) 0.271(3) 0.4729(8) 0.041(6) Uiso 1 1 d .
H1X H 0.527(2) 0.239(3) 0.4503(8) 0.041(7) Uiso 1 1 d .
H3X H 0.366(3) 0.492(4) 0.5155(12) 0.075(12) Uiso 1 1 d .
H4X H 0.291(3) 0.425(5) 0.4974(10) 0.074(12) Uiso 1 1 d .
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
N1 C1 C2 113.03(13) . .
N1 C1 H1A 109.0 . .
C2 C1 H1A 109.0 . .
N1 C1 H1B 109.0 . .
C2 C1 H1B 109.0 . .
H1A C1 H1B 107.8 . .
C7 C2 C3 119.13(16) . .
C7 C2 C1 120.70(16) . .
C3 C2 C1 120.17(15) . .
C2 C3 C4 120.30(17) . .
C2 C3 H3 119.9 . .
C4 C3 H3 119.9 . .
C5 C4 C3 120.19(18) . .
C5 C4 H4 119.9 . .
C3 C4 H4 119.9 . .
C4 C5 C6 119.85(18) . .
C4 C5 H5 120.1 . .
C6 C5 H5 120.1 . .
C5 C6 C7 120.46(19) . .
C5 C6 H6 119.8 . .
C7 C6 H6 119.8 . .
C6 C7 C2 120.07(18) . .
C6 C7 H7 120.0 . .
C2 C7 H7 120.0 . .
N1 C8 C9 102.48(12) . .
N1 C8 H8A 111.3 . .
C9 C8 H8A 111.3 . .
N1 C8 H8B 111.3 . .
C9 C8 H8B 111.3 . .
H8A C8 H8B 109.2 . .
C10 C9 C12 124.98(14) . .
C10 C9 C8 110.20(13) . .
C12 C9 C8 124.43(14) . .
O2 C10 C9 132.96(15) . .
O2 C10 C11 119.87(14) . .
C9 C10 C11 107.16(13) . .
O4 C11 N1 126.30(14) . .
O4 C11 C10 126.53(14) . .
N1 C11 C10 107.17(13) . .
O1 C12 O5 121.48(14) . .
O1 C12 C9 125.10(14) . .
O5 C12 C9 113.41(13) . .
O5 C13 C14 106.42(14) . .
O5 C13 H13A 110.4 . .
C14 C13 H13A 110.4 . .
O5 C13 H13B 110.4 . .
C14 C13 H13B 110.4 . .
H13A C13 H13B 108.6 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C11 N1 C8 112.98(13) . .
C11 N1 C1 123.51(14) . .
C8 N1 C1 123.45(14) . .
C12 O1 Zn1 123.65(10) . .
C10 O2 Zn1 120.34(10) . .
C12 O5 C13 116.30(12) . .
Zn1 O1S H2X 116.1(15) . .
Zn1 O1S H1X 113.1(17) . .
H2X O1S H1X 105(2) . .
O2 Zn1 O2 180.00(6) . 5_656
O2 Zn1 O1S 90.24(5) . 5_656
O2 Zn1 O1S 89.76(5) 5_656 5_656
O2 Zn1 O1S 89.76(5) . .
O2 Zn1 O1S 90.24(5) 5_656 .
O1S Zn1 O1S 180.00(6) 5_656 .
O2 Zn1 O1 92.40(4) . .
O2 Zn1 O1 87.60(4) 5_656 .
O1S Zn1 O1 89.98(5) 5_656 .
O1S Zn1 O1 90.02(5) . .
O2 Zn1 O1 87.60(4) . 5_656
O2 Zn1 O1 92.40(4) 5_656 5_656
O1S Zn1 O1 90.02(5) 5_656 5_656
O1S Zn1 O1 89.98(5) . 5_656
O1 Zn1 O1 180.0 . 5_656
H3X O2S H4X 105(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.462(2) .
C1 C2 1.514(2) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 C7 1.389(2) .
C2 C3 1.389(3) .
C3 C4 1.390(3) .
C3 H3 0.9500 .
C4 C5 1.372(3) .
C4 H4 0.9500 .
C5 C6 1.382(3) .
C5 H5 0.9500 .
C6 C7 1.384(3) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C8 N1 1.456(2) .
C8 C9 1.501(2) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.372(2) .
C9 C12 1.431(2) .
C10 O2 1.2726(19) .
C10 C11 1.505(2) .
C11 O4 1.2386(19) .
C11 N1 1.342(2) .
C12 O1 1.2392(19) .
C12 O5 1.3400(19) .
C13 O5 1.4574(19) .
C13 C14 1.506(2) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
O1 Zn1 2.1431(11) .
O2 Zn1 2.0022(11) .
O1S Zn1 2.1185(13) .
O1S H2X 0.86(3) .
O1S H1X 0.81(2) .
Zn1 O2 2.0022(11) 5_656
Zn1 O1S 2.1185(13) 5_656
Zn1 O1 2.1431(11) 5_656
O2S H3X 0.80(3) .
O2S H4X 0.69(4) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168302419
