#------------------------------------------------------------------------------
#$Date: 2016-03-25 12:39:45 +0100 (vie 25 de mar de 2016) $
#$Revision: 179856 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/52/7015293.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_7015293
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         'C24 H28 N4 O8 Zn2'
_chemical_formula_sum            'C24 H28 N4 O8 Zn2'
_chemical_formula_weight         631.24
_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                93.178(2)
_cell_angle_beta                 103.423(3)
_cell_angle_gamma                111.763(2)
_cell_formula_units_Z            1
_cell_length_a                   8.0218(4)
_cell_length_b                   8.8006(3)
_cell_length_c                   10.3280(5)
_cell_measurement_reflns_used    1847
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.93
_cell_measurement_theta_min      2.84
_cell_volume                     650.53(5)
_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      150(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0545
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6173
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.84
_exptl_absorpt_coefficient_mu    1.899
_exptl_absorpt_correction_T_max  0.8629
_exptl_absorpt_correction_T_min  0.6381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2320
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0423P)²+0.0048P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0793
_reflns_number_gt                1915
_reflns_number_total             2320
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0dt01457e.txt
_cod_data_source_block           Compound5
_cod_original_cell_volume        650.52(5)
_cod_database_code               7015293
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
Zn1 Zn 0.41933(5) 0.33715(4) 0.39891(4) 0.01735(13) Uani 1 1 d . . .
O1 O 0.3615(3) 0.5353(2) 0.4263(2) 0.0183(5) Uani 1 1 d . . .
O2 O -0.1598(3) -0.3006(3) 0.3005(2) 0.0305(6) Uani 1 1 d . . .
O3 O 0.1913(3) 0.1724(2) 0.2593(2) 0.0212(5) Uani 1 1 d . . .
O4 O 0.5886(3) 0.3976(3) 0.2771(2) 0.0244(5) Uani 1 1 d . . .
H4 H 0.664(5) 0.486(4) 0.286(4) 0.029 Uiso 1 1 d . . .
N1 N 0.3854(3) 0.1553(3) 0.5136(3) 0.0162(5) Uani 1 1 d . . .
N2 N 0.2556(3) 0.0101(3) 0.4950(3) 0.0177(6) Uani 1 1 d . . .
C1 C 0.1105(4) -0.0521(3) 0.3814(3) 0.0174(7) Uani 1 1 d . . .
C2 C -0.0162(4) -0.2179(4) 0.3906(3) 0.0208(7) Uani 1 1 d . . .
C3 C 0.0325(4) -0.2896(4) 0.5158(4) 0.0258(8) Uani 1 1 d . . .
H3A H -0.0718 -0.3930 0.5151 0.039 Uiso 1 1 calc R . .
H3B H 0.0570 -0.2104 0.5954 0.039 Uiso 1 1 calc R . .
H3C H 0.1440 -0.3120 0.5185 0.039 Uiso 1 1 calc R . .
C4 C 0.0795(4) 0.0301(4) 0.2681(3) 0.0192(7) Uani 1 1 d . . .
C5 C -0.0920(4) -0.0475(4) 0.1517(4) 0.0299(8) Uani 1 1 d . . .
H5A H -0.0911 0.0295 0.0866 0.045 Uiso 1 1 calc R . .
H5B H -0.2032 -0.0728 0.1844 0.045 Uiso 1 1 calc R . .
H5C H -0.0938 -0.1500 0.1079 0.045 Uiso 1 1 calc R . .
C6 C 0.5212(4) 0.1998(4) 0.6401(3) 0.0175(7) Uani 1 1 d . . .
C7 C 0.6514(4) 0.3652(4) 0.6677(3) 0.0168(7) Uani 1 1 d . . .
C8 C 0.7905(4) 0.4203(4) 0.7898(3) 0.0233(7) Uani 1 1 d . . .
H8 H 0.8800 0.5314 0.8101 0.028 Uiso 1 1 calc R . .
C9 C 0.7971(5) 0.3122(4) 0.8811(4) 0.0294(8) Uani 1 1 d . . .
H9 H 0.8917 0.3502 0.9642 0.035 Uiso 1 1 calc R . .
C10 C 0.6696(4) 0.1509(4) 0.8539(3) 0.0272(8) Uani 1 1 d . . .
H10 H 0.6768 0.0787 0.9181 0.033 Uiso 1 1 calc R . .
C11 C 0.5305(4) 0.0929(4) 0.7333(3) 0.0228(7) Uani 1 1 d . . .
H11 H 0.4422 -0.0187 0.7145 0.027 Uiso 1 1 calc R . .
C12 C 0.5325(6) 0.3484(5) 0.1349(4) 0.0542(12) Uani 1 1 d . . .
H12A H 0.4711 0.2274 0.1136 0.081 Uiso 1 1 calc R . .
H12B H 0.6423 0.3870 0.1000 0.081 Uiso 1 1 calc R . .
H12C H 0.4454 0.3971 0.0930 0.081 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'
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
O1 Zn1 O4 103.86(9) . . ?
O1 Zn1 N1 126.31(9) . . ?
O4 Zn1 N1 127.15(9) . . ?
O1 Zn1 O3 104.79(8) . . ?
O4 Zn1 O3 96.89(9) . . ?
N1 Zn1 O3 86.38(9) . . ?
O1 Zn1 O1 81.84(8) . 2_666 ?
O4 Zn1 O1 93.10(8) . 2_666 ?
N1 Zn1 O1 80.03(9) . 2_666 ?
O3 Zn1 O1 166.23(8) . 2_666 ?
O1 Zn1 Zn1 42.41(6) . 2_666 ?
O4 Zn1 Zn1 100.98(7) . 2_666 ?
N1 Zn1 Zn1 105.19(8) . 2_666 ?
O3 Zn1 Zn1 145.65(6) . 2_666 ?
O1 Zn1 Zn1 39.43(5) 2_666 2_666 ?
C7 O1 Zn1 123.89(19) 2_666 . ?
C7 O1 Zn1 111.93(17) 2_666 2_666 ?
Zn1 O1 Zn1 98.16(8) . 2_666 ?
C4 O3 Zn1 129.8(2) . . ?
C12 O4 Zn1 125.4(2) . . ?
C12 O4 H4 103(3) . . ?
Zn1 O4 H4 121(3) . . ?
N2 N1 C6 114.6(2) . . ?
N2 N1 Zn1 130.9(2) . . ?
C6 N1 Zn1 114.39(19) . . ?
N1 N2 C1 122.9(3) . . ?
N2 C1 C4 126.4(3) . . ?
N2 C1 C2 110.4(3) . . ?
C4 C1 C2 123.3(3) . . ?
O2 C2 C1 122.9(3) . . ?
O2 C2 C3 119.3(3) . . ?
C1 C2 C3 117.8(3) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O3 C4 C1 123.1(3) . . ?
O3 C4 C5 115.4(3) . . ?
C1 C4 C5 121.5(3) . . ?
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 . . ?
C11 C6 C7 120.5(3) . . ?
C11 C6 N1 124.6(3) . . ?
C7 C6 N1 114.9(3) . . ?
O1 C7 C8 122.4(3) 2_666 . ?
O1 C7 C6 118.6(3) 2_666 . ?
C8 C7 C6 119.0(3) . . ?
C9 C8 C7 119.6(3) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C10 C9 C8 121.3(3) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C6 119.3(3) . . ?
C10 C11 H11 120.3 . . ?
C6 C11 H11 120.3 . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
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 O1 1.986(2) . ?
Zn1 O4 2.011(2) . ?
Zn1 N1 2.019(2) . ?
Zn1 O3 2.025(2) . ?
Zn1 O1 2.109(2) 2_666 ?
Zn1 Zn1 3.0955(7) 2_666 ?
O1 C7 1.354(3) 2_666 ?
O1 Zn1 2.109(2) 2_666 ?
O2 C2 1.236(4) . ?
O3 C4 1.264(3) . ?
O4 C12 1.423(4) . ?
O4 H4 0.77(4) . ?
N1 N2 1.283(3) . ?
N1 C6 1.419(4) . ?
N2 C1 1.361(4) . ?
C1 C4 1.431(4) . ?
C1 C2 1.460(4) . ?
C2 C3 1.503(5) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.500(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C11 1.392(4) . ?
C6 C7 1.407(4) . ?
C7 O1 1.354(3) 2_666 ?
C7 C8 1.396(4) . ?
C8 C9 1.382(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.373(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
