#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:39:45 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179856 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/52/7015294.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_7015294
loop_
_publ_author_name
'Kopylovich, Maximilian N.'
'Mac Leod, Tatiana C. O.'
'Mahmudov, Kamran T.'
'Guedes da Silva, M Fátima C'
'Pombeiro, Armando J. L.'
_publ_section_title
;
 Zinc(ii) ortho-hydroxyphenylhydrazo-β-diketonate complexes and their
 catalytic ability towards diastereoselective nitroaldol (Henry)
 reaction.
;
_journal_issue                   19
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5352
_journal_page_last               5361
_journal_paper_doi               10.1039/c0dt01457e
_journal_volume                  40
_journal_year                    2011
_chemical_formula_moiety         'C13 H17 N3 O7 S Zn'
_chemical_formula_sum            'C13 H17 N3 O7 S Zn'
_chemical_formula_weight         424.73
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                115.83(2)
_cell_angle_beta                 106.16(2)
_cell_angle_gamma                90.23(3)
_cell_formula_units_Z            2
_cell_length_a                   8.782(6)
_cell_length_b                   10.621(9)
_cell_length_c                   10.703(9)
_cell_measurement_reflns_used    481
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.04
_cell_measurement_theta_min      2.29
_cell_volume                     854.0(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.912
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0813
_diffrn_reflns_av_sigmaI/netI    0.1877
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4652
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    1.602
_exptl_absorpt_correction_T_max  0.8745
_exptl_absorpt_correction_T_min  0.7741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       0.0030(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.839
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         2859
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.839
_refine_ls_R_factor_all          0.1659
_refine_ls_R_factor_gt           0.0603
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0213P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0797
_refine_ls_wR_factor_ref         0.0979
_reflns_number_gt                1321
_reflns_number_total             2859
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0dt01457e.txt
_cod_data_source_block           Compound6
_cod_database_code               7015294
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6401(7) -0.0448(6) 0.7823(7) 0.0306(17) Uani 1 1 d . . .
C2 C 0.6380(7) 0.0510(6) 0.9220(6) 0.0269(16) Uani 1 1 d . . .
C3 C 0.7322(8) 0.0428(7) 1.0429(7) 0.043(2) Uani 1 1 d . . .
H3 H 0.7292 0.1091 1.1367 0.051 Uiso 1 1 calc R . .
C4 C 0.8326(8) -0.0603(7) 1.0320(7) 0.0404(19) Uani 1 1 d . . .
H4 H 0.8972 -0.0660 1.1163 0.049 Uiso 1 1 calc R . .
C5 C 0.8344(8) -0.1516(7) 0.8972(8) 0.0377(19) Uani 1 1 d . . .
C6 C 0.7392(8) -0.1493(7) 0.7690(7) 0.0407(19) Uani 1 1 d . . .
H6 H 0.7422 -0.2170 0.6758 0.049 Uiso 1 1 calc R . .
C11 C 0.2319(8) 0.4912(7) 0.9895(7) 0.054(2) Uani 1 1 d . . .
H11A H 0.3045 0.5810 1.0459 0.081 Uiso 1 1 calc R . .
H11B H 0.1646 0.4841 1.0461 0.081 Uiso 1 1 calc R . .
H11C H 0.1638 0.4869 0.8976 0.081 Uiso 1 1 calc R . .
C12 C 0.3288(8) 0.3700(7) 0.9568(7) 0.0379(18) Uani 1 1 d . . .
C13 C 0.4472(8) 0.3534(7) 1.0697(7) 0.0372(19) Uani 1 1 d . . .
C14 C 0.4856(9) 0.4528(7) 1.2234(7) 0.046(2) Uani 1 1 d . . .
C15 C 0.6171(9) 0.4325(8) 1.3351(7) 0.076(3) Uani 1 1 d . . .
H15A H 0.6353 0.5133 1.4313 0.114 Uiso 1 1 calc R . .
H15B H 0.7159 0.4254 1.3082 0.114 Uiso 1 1 calc R . .
H15C H 0.5859 0.3456 1.3383 0.114 Uiso 1 1 calc R . .
C21 C 0.0060(9) -0.2636(8) 0.4901(8) 0.083(3) Uani 1 1 d . . .
H21A H 0.0068 -0.2526 0.5861 0.124 Uiso 1 1 calc R . .
H21B H -0.0077 -0.3644 0.4223 0.124 Uiso 1 1 calc R . .
H21C H -0.0827 -0.2208 0.4529 0.124 Uiso 1 1 calc R . .
C22 C 0.1335(9) -0.1832(8) 0.3337(7) 0.076(3) Uani 1 1 d . . .
H22A H 0.0454 -0.1280 0.3257 0.114 Uiso 1 1 calc R . .
H22B H 0.0986 -0.2812 0.2577 0.114 Uiso 1 1 calc R . .
H22C H 0.2253 -0.1426 0.3212 0.114 Uiso 1 1 calc R . .
N1 N 0.5350(6) 0.1530(5) 0.9227(5) 0.0314(14) Uani 1 1 d . . .
N2 N 0.5424(6) 0.2483(6) 1.0504(5) 0.0355(15) Uani 1 1 d . . .
N5 N 0.9351(7) -0.2644(7) 0.8779(8) 0.0538(18) Uani 1 1 d . . .
O1 O 0.1939(5) -0.0242(5) 0.6129(5) 0.0546(15) Uani 1 1 d . . .
O2 O 0.2990(5) 0.2845(5) 0.8253(5) 0.0479(14) Uani 1 1 d . . .
O4 O 0.4101(6) 0.5527(5) 1.2690(5) 0.0714(18) Uani 1 1 d . . .
O5 O 0.9427(7) -0.3435(6) 0.7572(6) 0.086(2) Uani 1 1 d . . .
O6 O 1.0157(7) -0.2687(6) 0.9896(6) 0.0765(19) Uani 1 1 d . . .
O10 O 0.4148(6) 0.1890(5) 0.5805(4) 0.0518(14) Uani 1 1 d . . .
O11 O 0.5493(5) -0.0346(5) 0.6663(4) 0.0474(14) Uani 1 1 d . . .
Zn1 Zn 0.39845(11) 0.11170(9) 0.71797(8) 0.0401(3) Uani 1 1 d . . .
S1 S 0.1894(2) -0.1791(2) 0.5063(2) 0.0573(7) Uani 1 1 d . . .
H10A H 0.4571 0.1227 0.5074 0.086 Uiso 1 1 d . . .
H10B H 0.4886 0.2768 0.6349 0.086 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'
S S 0.1246 0.1234 '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
O11 C1 C6 121.5(6) . . ?
O11 C1 C2 119.8(6) . . ?
C6 C1 C2 118.7(6) . . ?
C3 C2 C1 120.6(6) . . ?
C3 C2 N1 125.5(6) . . ?
C1 C2 N1 113.9(5) . . ?
C2 C3 C4 121.6(6) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 117.4(6) . . ?
C5 C4 H4 121.3 . . ?
C3 C4 H4 121.3 . . ?
C4 C5 C6 123.6(6) . . ?
C4 C5 N5 120.1(6) . . ?
C6 C5 N5 116.3(6) . . ?
C1 C6 C5 118.2(6) . . ?
C1 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 C13 121.8(6) . . ?
O2 C12 C11 115.8(6) . . ?
C13 C12 C11 122.4(6) . . ?
N2 C13 C12 126.5(6) . . ?
N2 C13 C14 110.7(6) . . ?
C12 C13 C14 122.8(6) . . ?
O4 C14 C13 122.7(7) . . ?
O4 C14 C15 117.4(6) . . ?
C13 C14 C15 119.8(6) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
S1 C21 H21A 109.5 . . ?
S1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
S1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
S1 C22 H22A 109.5 . . ?
S1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
S1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N2 N1 C2 114.4(5) . . ?
N2 N1 Zn1 133.4(4) . . ?
C2 N1 Zn1 112.2(4) . . ?
N1 N2 C13 121.5(5) . . ?
O5 N5 O6 122.9(7) . . ?
O5 N5 C5 120.5(7) . . ?
O6 N5 C5 116.5(7) . . ?
S1 O1 Zn1 121.6(3) . . ?
C12 O2 Zn1 132.9(4) . . ?
Zn1 O10 H10A 109.2 . . ?
Zn1 O10 H10B 108.9 . . ?
H10A O10 H10B 108.3 . . ?
C1 O11 Zn1 112.3(4) . . ?
O1 Zn1 O10 104.3(2) . . ?
O1 Zn1 N1 122.3(2) . . ?
O10 Zn1 N1 133.3(2) . . ?
O1 Zn1 O11 96.9(2) . . ?
O10 Zn1 O11 97.13(19) . . ?
N1 Zn1 O11 80.74(18) . . ?
O1 Zn1 O2 96.2(2) . . ?
O10 Zn1 O2 89.23(18) . . ?
N1 Zn1 O2 83.86(19) . . ?
O11 Zn1 O2 163.56(17) . . ?
O1 S1 C22 104.5(3) . . ?
O1 S1 C21 103.8(3) . . ?
C22 S1 C21 98.0(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
C1 O11 1.326(6) . ?
C1 C6 1.396(8) . ?
C1 C2 1.401(8) . ?
C2 C3 1.367(8) . ?
C2 N1 1.413(7) . ?
C3 C4 1.394(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.348(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.404(8) . ?
C5 N5 1.468(8) . ?
C6 H6 0.9500 . ?
C11 C12 1.511(8) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O2 1.246(7) . ?
C12 C13 1.436(8) . ?
C13 N2 1.375(7) . ?
C13 C14 1.452(8) . ?
C14 O4 1.240(7) . ?
C14 C15 1.506(8) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C21 S1 1.768(8) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 S1 1.755(7) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
N1 N2 1.281(6) . ?
N1 Zn1 2.032(5) . ?
N5 O5 1.217(7) . ?
N5 O6 1.228(7) . ?
O1 S1 1.532(4) . ?
O1 Zn1 2.004(5) . ?
O2 Zn1 2.046(4) . ?
O10 Zn1 2.007(4) . ?
O10 H10A 0.964 . ?
O10 H10B 0.970 . ?
O11 Zn1 2.037(4) . ?
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
O11 C1 C2 C3 -179.3(6) . . . . ?
C6 C1 C2 C3 0.5(9) . . . . ?
O11 C1 C2 N1 -0.4(8) . . . . ?
C6 C1 C2 N1 179.3(6) . . . . ?
C1 C2 C3 C4 -0.2(10) . . . . ?
N1 C2 C3 C4 -178.9(6) . . . . ?
C2 C3 C4 C5 0.5(10) . . . . ?
C3 C4 C5 C6 -1.2(11) . . . . ?
C3 C4 C5 N5 -178.8(6) . . . . ?
O11 C1 C6 C5 178.7(6) . . . . ?
C2 C1 C6 C5 -1.1(10) . . . . ?
C4 C5 C6 C1 1.5(11) . . . . ?
N5 C5 C6 C1 179.2(6) . . . . ?
O2 C12 C13 N2 1.4(11) . . . . ?
C11 C12 C13 N2 -179.0(6) . . . . ?
O2 C12 C13 C14 179.1(6) . . . . ?
C11 C12 C13 C14 -1.2(10) . . . . ?
N2 C13 C14 O4 -176.1(7) . . . . ?
C12 C13 C14 O4 5.8(11) . . . . ?
N2 C13 C14 C15 1.1(9) . . . . ?
C12 C13 C14 C15 -176.9(7) . . . . ?
C3 C2 N1 N2 4.4(9) . . . . ?
C1 C2 N1 N2 -174.3(5) . . . . ?
C3 C2 N1 Zn1 -173.3(5) . . . . ?
C1 C2 N1 Zn1 8.0(6) . . . . ?
C2 N1 N2 C13 -178.6(6) . . . . ?
Zn1 N1 N2 C13 -1.6(9) . . . . ?
C12 C13 N2 N1 1.6(10) . . . . ?
C14 C13 N2 N1 -176.4(5) . . . . ?
C4 C5 N5 O5 -176.9(7) . . . . ?
C6 C5 N5 O5 5.3(10) . . . . ?
C4 C5 N5 O6 -0.5(10) . . . . ?
C6 C5 N5 O6 -178.3(6) . . . . ?
C13 C12 O2 Zn1 -4.4(10) . . . . ?
C11 C12 O2 Zn1 175.9(4) . . . . ?
C6 C1 O11 Zn1 172.9(5) . . . . ?
C2 C1 O11 Zn1 -7.3(7) . . . . ?
S1 O1 Zn1 O10 87.6(3) . . . . ?
S1 O1 Zn1 N1 -95.0(3) . . . . ?
S1 O1 Zn1 O11 -11.6(3) . . . . ?
S1 O1 Zn1 O2 178.4(3) . . . . ?
N2 N1 Zn1 O1 -93.9(6) . . . . ?
C2 N1 Zn1 O1 83.3(4) . . . . ?
N2 N1 Zn1 O10 82.7(6) . . . . ?
C2 N1 Zn1 O10 -100.2(5) . . . . ?
N2 N1 Zn1 O11 173.8(6) . . . . ?
C2 N1 Zn1 O11 -9.1(4) . . . . ?
N2 N1 Zn1 O2 -0.4(6) . . . . ?
C2 N1 Zn1 O2 176.7(4) . . . . ?
C1 O11 Zn1 O1 -112.9(4) . . . . ?
C1 O11 Zn1 O10 141.7(4) . . . . ?
C1 O11 Zn1 N1 8.9(4) . . . . ?
C1 O11 Zn1 O2 29.6(10) . . . . ?
C12 O2 Zn1 O1 125.5(6) . . . . ?
C12 O2 Zn1 O10 -130.1(6) . . . . ?
C12 O2 Zn1 N1 3.6(6) . . . . ?
C12 O2 Zn1 O11 -17.0(12) . . . . ?
Zn1 O1 S1 C22 -95.8(4) . . . . ?
Zn1 O1 S1 C21 162.0(3) . . . . ?
