#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:46:28 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178700 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/11/4081178.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_4081178
loop_
_publ_author_name
'Voronova, Krisztina'
'Purgel, Mihály'
'Udvardy, Antal'
'Bényei, Attila C.'
'Kathó, Ágnes'
'Joó, Ferenc'
_publ_section_title
;
 Hydrogenation and Redox Isomerization of Allylic Alcohols Catalyzed by a
 New Water-Soluble Pd--tetrahydrosalen Complex
;
_journal_issue                   15
_journal_name_full               Organometallics
_journal_page_first              4391
_journal_paper_doi               10.1021/om400555u
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         'C10 H16 N1 O5 S2'
_chemical_formula_sum            'C10 H16 N O5 S2'
_chemical_formula_weight         294.36
_chemical_name_systematic
;
 ?
;
_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_date             2013-05-18T14:09:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 124.073(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5820(10)
_cell_length_b                   6.5740(10)
_cell_length_c                   16.592(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      16.1
_cell_measurement_theta_min      4.6
_cell_volume                     1317.5(3)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius MACH3'
_diffrn_measurement_method       'non-profiled ω/2τ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.1152
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            2772
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         2.96
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        17
_diffrn_standards_interval_count 89
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.416
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.688
_refine_diff_density_min         -0.52
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2772
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.2265
_refine_ls_R_factor_gt           0.0864
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0688P)²+3.0755P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2258
_reflns_number_gt                1039
_reflns_number_total             2772
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            om400555u_si_002.cif
_cod_data_source_block           sulfosalan
_cod_database_code               4081178
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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.1094(8) 0.2272(14) 0.3490(7) 0.032(3) Uani d . 1 . . C
C2 0.1512(8) 0.0284(14) 0.3746(7) 0.032(3) Uani d . 1 . . C
C3 0.2187(8) -0.0467(16) 0.3476(7) 0.040(3) Uani d . 1 . . C
H3 0.2454 -0.1791 0.3644 0.048 Uiso calc . 1 . . H
C4 0.2473(8) 0.0714(17) 0.2962(7) 0.038(3) Uani d . 1 . . C
H4 0.2929 0.0181 0.2787 0.046 Uiso calc . 1 . . H
C5 0.2091(8) 0.2662(15) 0.2709(7) 0.033(3) Uani d . 1 . . C
C6 0.1396(8) 0.3425(14) 0.2976(7) 0.031(3) Uani d . 1 . . C
H6 0.113 0.4748 0.2801 0.038 Uiso calc . 1 . . H
C11 0.0329(8) 0.3116(15) 0.3723(7) 0.040(3) Uani d . 1 . . C
H11A -0.0349 0.2327 0.3387 0.048 Uiso calc R 1 . . H
H11B 0.0143 0.4503 0.3485 0.048 Uiso calc R 1 . . H
C12 0.0053(10) 0.3870(15) 0.5056(8) 0.044(3) Uani d . 1 . . C
H12A 0.0346 0.3506 0.5725 0.053 Uiso calc R 1 . . H
H12B -0.0671 0.3246 0.4643 0.053 Uiso calc R 1 . . H
N1 0.0807(7) 0.3101(12) 0.4783(6) 0.039(2) Uani d . 1 . . N
H1A 0.1426 0.3865 0.5086 0.047 Uiso calc R 1 . . H
H1B 0.1006 0.1818 0.5003 0.047 Uiso calc R 1 . . H
O1 0.1230(6) -0.0852(11) 0.4255(5) 0.052(2) Uani d D 1 . . O
H1 0.0817 -0.0194 0.4345 0.078 Uiso calc D 1 . . H
O11 0.3179(6) 0.5777(12) 0.2768(5) 0.067(2) Uani d . 1 . . O
O12 0.2986(7) 0.2978(12) 0.1744(6) 0.061(2) Uani d . 1 . . O
O13 0.1424(6) 0.5108(11) 0.1271(5) 0.052(2) Uani d . 1 . . O
S1 0.2457(2) 0.4269(5) 0.2074(2) 0.0408(8) Uani d . 1 . . S
O21 0.426(2) 0.797(3) 0.605(2) 0.127(16) Uani d PD 0.359(14) A 1 O
S21 0.3654(7) 0.5675(14) 0.6116(8) 0.048(4) Uani d PD 0.359(14) A 1 S
C21 0.2513(14) 0.584(4) 0.5087(13) 0.000(6) Uiso d PD 0.359(14) A 1 C
H21A 0.2034 0.6771 0.513 0 Uiso calc PR 0.359(14) A 1 H
H21B 0.217 0.4527 0.4893 0 Uiso calc PR 0.359(14) A 1 H
H21C 0.2644 0.6334 0.4615 0 Uiso calc PR 0.359(14) A 1 H
C22 0.414(3) 0.408(8) 0.570(4) 0.28(6) Uiso d PD 0.359(14) A 1 C
H22A 0.4878 0.3703 0.621 0.423 Uiso calc PR 0.359(14) A 1 H
H22B 0.4141 0.4702 0.5177 0.423 Uiso calc PR 0.359(14) A 1 H
H22C 0.3677 0.2888 0.5461 0.423 Uiso calc PR 0.359(14) A 1 H
O21A 0.4272(19) 0.622(3) 0.6841(12) 0.162(10) Uani d PD 0.641(14) A 2 O
S21A 0.3671(5) 0.6091(10) 0.5563(5) 0.066(2) Uani d PD 0.641(14) A 2 S
C21A 0.2423(9) 0.598(3) 0.5238(10) 0.013(5) Uiso d PD 0.641(14) A 2 C
H21D 0.2177 0.7306 0.5274 0.019 Uiso calc PR 0.641(14) A 2 H
H21E 0.2366 0.5065 0.566 0.019 Uiso calc PR 0.641(14) A 2 H
H21F 0.1969 0.5486 0.4581 0.019 Uiso calc PR 0.641(14) A 2 H
C22A 0.4087(13) 0.377(2) 0.5506(13) 0.040(5) Uiso d PD 0.641(14) A 2 C
H22D 0.4844 0.3829 0.5704 0.06 Uiso calc PR 0.641(14) A 2 H
H22E 0.3631 0.3278 0.4851 0.06 Uiso calc PR 0.641(14) A 2 H
H22F 0.4026 0.288 0.5932 0.06 Uiso calc PR 0.641(14) A 2 H
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 0 '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 0.006 '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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-4 0 8
3 1 -2
1 -1 2
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
C6 C1 C2 117.5(9) . .
C6 C1 C11 120.2(9) . .
C2 C1 C11 122.3(9) . .
O1 C2 C3 121.8(9) . .
O1 C2 C1 118.0(9) . .
C3 C2 C1 120.1(9) . .
C4 C3 C2 121.1(10) . .
C4 C3 H3 119.4 . .
C2 C3 H3 119.4 . .
C5 C4 C3 120.4(9) . .
C5 C4 H4 119.8 . .
C3 C4 H4 119.8 . .
C4 C5 C6 118.6(10) . .
C4 C5 S1 122.4(8) . .
C6 C5 S1 119.0(8) . .
C1 C6 C5 122.2(9) . .
C1 C6 H6 118.9 . .
C5 C6 H6 118.9 . .
C1 C11 N1 112.6(8) . .
C1 C11 H11A 109.1 . .
N1 C11 H11A 109.1 . .
C1 C11 H11B 109.1 . .
N1 C11 H11B 109.1 . .
H11A C11 H11B 107.8 . .
N1 C12 C12 109.9(11) . 3_566
N1 C12 H12A 109.7 . .
C12 C12 H12A 109.7 3_566 .
N1 C12 H12B 109.7 . .
C12 C12 H12B 109.7 3_566 .
H12A C12 H12B 108.2 . .
C11 N1 C12 114.9(8) . .
C11 N1 H1A 108.5 . .
C12 N1 H1A 108.5 . .
C11 N1 H1B 108.5 . .
C12 N1 H1B 108.5 . .
H1A N1 H1B 107.5 . .
C2 O1 H1 109.5 . .
O11 S1 O12 113.7(5) . .
O11 S1 O13 113.1(5) . .
O12 S1 O13 112.1(5) . .
O11 S1 C5 105.3(5) . .
O12 S1 C5 106.1(5) . .
O13 S1 C5 105.7(4) . .
C21 S21 C22 91.7(12) . .
C21 S21 O21 97.6(13) . .
C22 S21 O21 100(2) . .
S21 C21 H21A 109.5 . .
S21 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
S21 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
S21 C22 H22A 109.5 . .
S21 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
S21 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C21A S21A C22A 108.8(9) . .
C21A S21A O21A 96.6(10) . .
C22A S21A O21A 99.1(10) . .
S21A C21A H21D 109.5 . .
S21A C21A H21E 109.5 . .
H21D C21A H21E 109.5 . .
S21A C21A H21F 109.5 . .
H21D C21A H21F 109.5 . .
H21E C21A H21F 109.5 . .
S21A C22A H22D 109.5 . .
S21A C22A H22E 109.5 . .
H22D C22A H22E 109.5 . .
S21A C22A H22F 109.5 . .
H22D C22A H22F 109.5 . .
H22E C22A H22F 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C6 . 1.384(13)
C1 C2 . 1.404(13)
C1 C11 . 1.477(12)
C2 O1 . 1.353(10)
C2 C3 . 1.381(13)
C3 C4 . 1.378(13)
C3 H3 . 0.93
C4 C5 . 1.365(14)
C4 H4 . 0.93
C5 C6 . 1.407(13)
C5 S1 . 1.772(11)
C6 H6 . 0.93
C11 N1 . 1.485(10)
C11 H11A . 0.97
C11 H11B . 0.97
C12 N1 . 1.494(12)
C12 C12 3_566 1.495(19)
C12 H12A . 0.97
C12 H12B . 0.97
N1 H1A . 0.9
N1 H1B . 0.9
O1 H1 . 0.82
O11 S1 . 1.435(7)
O12 S1 . 1.445(7)
O13 S1 . 1.449(7)
O21 S21 . 1.780(17)
S21 C21 . 1.585(13)
S21 C22 . 1.618(16)
C21 H21A . 0.96
C21 H21B . 0.96
C21 H21C . 0.96
C22 H22A . 0.96
C22 H22B . 0.96
C22 H22C . 0.96
O21A S21A . 1.784(16)
S21A C21A . 1.583(12)
S21A C22A . 1.661(14)
C21A H21D . 0.96
C21A H21E . 0.96
C21A H21F . 0.96
C22A H22D . 0.96
C22A H22E . 0.96
C22A H22F . 0.96
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
N1 H1A O12 0.9 2.68 3.098(11) 109.3 4_566
N1 H1B O13 0.9 2.23 2.978(11) 140.5 4_566
N1 H1B O1 0.9 2.28 2.916(10) 127.8 .
O1 H1 N1 0.82 2.29 2.916(10) 133.9 .
N1 H1B S1 0.9 2.94 3.524(8) 124 4_566
