# Supplementary Material (ESI) for Metallomics
# This journal is (c) The Royal Society of Chemistry 2011
data_global
_journal_coden_Cambridge 1400
loop_
_publ_author_name
'Kawarada, Hikaru'
'Yoshikawa, Yutaka'
'Yasui, Hiroyuki'
'Kuwahara, Shunsuke'
'Habata, Yoichi'
'Tamaki, Makoto'
'Saito, Ryota'
_publ_contact_author_name 'Saito, Ryota'
_publ_contact_author_email saito@chem.sci.toho-u.ac.jp
_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
;
data_pbca
_database_code_depnum_ccdc_archive 'CCDC 809751'
#TrackingRef 'Pbca.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C28 H36 N2 O12 Zn'
_chemical_formula_weight 657.96
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'
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_H-M Pbca
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'
_cell_length_a 11.8469(7)
_cell_length_b 8.7118(5)
_cell_length_c 28.9529(17)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 2988.2(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 100
_cell_measurement_reflns_used ?
_cell_measurement_theta_min ?
_cell_measurement_theta_max ?
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.27
_exptl_crystal_size_mid 0.17
_exptl_crystal_size_min 0.12
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.463
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1376
_exptl_absorpt_coefficient_mu 0.888
_exptl_absorpt_correction_type empirical
_exptl_absorpt_correction_T_min 0.7974
_exptl_absorpt_correction_T_max 0.9048
_exptl_absorpt_process_details 'SADABS, Sheldrick, 1996'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 21051
_diffrn_reflns_av_R_equivalents 0.0393
_diffrn_reflns_av_sigmaI/netI 0.0302
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 15
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_l_min -32
_diffrn_reflns_limit_l_max 38
_diffrn_reflns_theta_min 1.41
_diffrn_reflns_theta_max 28.30
_reflns_number_total 3713
_reflns_number_gt 2920
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker SMART'
_computing_cell_refinement 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0626P)^2^+0.1653P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3713
_refine_ls_number_parameters 213
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0483
_refine_ls_R_factor_gt 0.0333
_refine_ls_wR_factor_ref 0.1041
_refine_ls_wR_factor_gt 0.0889
_refine_ls_goodness_of_fit_ref 1.087
_refine_ls_restrained_S_all 1.087
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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
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_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0278(9) 0.0215(8) 0.0240(8) 0.0006(6) 0.0076(7) 0.0059(7)
C2 0.0264(8) 0.0188(8) 0.0221(8) -0.0008(6) 0.0066(7) 0.0042(6)
C3 0.0269(8) 0.0321(10) 0.0269(9) -0.0023(7) 0.0045(7) 0.0032(7)
C4 0.0349(11) 0.0335(11) 0.0429(12) -0.0033(9) 0.0133(8) -0.0071(8)
C5 0.0591(14) 0.0355(12) 0.0346(11) 0.0087(8) 0.0153(10) -0.0080(10)
C6 0.0663(15) 0.0480(14) 0.0258(10) 0.0102(9) -0.0035(10) -0.0120(11)
C7 0.0410(11) 0.0319(10) 0.0284(9) 0.0024(7) -0.0018(8) -0.0083(8)
C8 0.0218(8) 0.0250(8) 0.0187(8) -0.0017(6) 0.0000(6) -0.0001(6)
C9 0.0188(8) 0.0215(8) 0.0178(7) -0.0008(6) 0.0006(6) 0.0006(6)
C10 0.0187(7) 0.0194(8) 0.0179(7) 0.0030(5) 0.0012(6) 0.0007(6)
C11 0.0206(7) 0.0195(8) 0.0172(7) 0.0046(6) 0.0020(6) 0.0023(6)
C12 0.0207(8) 0.0201(8) 0.0194(7) 0.0011(6) -0.0019(6) -0.0013(6)
C13 0.0195(8) 0.0316(9) 0.0241(8) -0.0012(7) -0.0001(6) -0.0059(7)
C14 0.0298(9) 0.0391(11) 0.0264(9) 0.0005(7) -0.0060(8) -0.0120(8)
N1 0.0215(7) 0.0225(7) 0.0199(7) -0.0014(5) 0.0041(5) 0.0019(5)
O1 0.0186(5) 0.0273(6) 0.0232(6) -0.0061(5) 0.0017(4) -0.0024(5)
O2 0.0184(5) 0.0267(6) 0.0221(6) -0.0061(5) 0.0020(4) -0.0017(5)
O4 0.0175(5) 0.0272(6) 0.0249(6) 0.0021(5) -0.0003(5) 0.0007(5)
O5 0.0193(6) 0.0306(7) 0.0230(6) -0.0064(5) 0.0000(5) -0.0054(5)
O1S 0.0191(6) 0.0257(7) 0.0288(6) 0.0007(5) 0.0040(5) 0.0000(5)
Zn1 0.01624(16) 0.02214(17) 0.01966(16) -0.00407(9) 0.00247(9) -0.00089(9)
O2S 0.0297(8) 0.0422(10) 0.0394(9) -0.0078(7) 0.0024(7) 0.0118(7)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
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_
_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
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) . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 28.30
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.533
_refine_diff_density_min -0.416
_refine_diff_density_rms 0.130