#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:41:59 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180515 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/84/7218429.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_7218429
loop_
_publ_author_name
'Xie, Jing-Bo'
'Bao, Jia-Jing'
'Li, Hong-Xi'
'Tan, Da-Wei'
'Li, Hai-Yan'
'Lang, Jian-Ping'
_publ_section_title
;
 An efficient approach to the ammoxidation of alcohols to nitriles and the
 aerobic oxidation of alcohols to aldehydes in water using Cu(II)/pypzacac
 complexes as catalysts
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA11743C
_journal_year                    2014
_chemical_formula_moiety         'C24 H30 Cu2 N6 O14 S2, 2(C O H4)'
_chemical_formula_sum            'C26 H38 Cu2 N6 O16 S2'
_chemical_formula_weight         881.82
_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                112.268(6)
_cell_angle_beta                 114.296(6)
_cell_angle_gamma                96.811(5)
_cell_formula_units_Z            1
_cell_length_a                   9.9313(5)
_cell_length_b                   10.6591(8)
_cell_length_c                   10.9968(6)
_cell_measurement_reflns_used    3882
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      28.1300
_cell_measurement_theta_min      3.4120
_cell_volume                     928.42(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '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  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8269
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    1.334
_exptl_absorpt_correction_T_max  0.8250
_exptl_absorpt_correction_T_min  0.6904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             454
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3449
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0421P)²+0.4148P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0919
_reflns_number_gt                2917
_reflns_number_total             3449
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra11743c2.cif
_cod_data_source_block           3
_cod_original_cell_volume        928.42(10)
_cod_database_code               7218429
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
Cu1 Cu 0.26731(4) 0.48508(3) 0.10815(4) 0.02382(13) Uani 1 1 d . . .
S1 S 0.05578(8) 0.65958(7) 0.19491(8) 0.02589(18) Uani 1 1 d . A .
O1 O 0.1350(3) -0.0424(3) -0.0507(3) 0.0568(7) Uani 1 1 d . . .
O2 O 0.3866(3) 0.0780(3) 0.1149(4) 0.0671(8) Uani 1 1 d . . .
O3 O 0.2265(3) 0.4163(3) 0.2592(4) 0.0654(8) Uani 1 1 d D . .
H3A H 0.163(4) 0.461(4) 0.264(5) 0.079 Uiso 1 1 d D . .
O4 O 0.1616(2) 0.6268(2) 0.1321(2) 0.0292(5) Uani 1 1 d . . .
O5 O 0.0145(2) 0.5516(2) 0.2353(2) 0.0364(5) Uani 1 1 d . . .
O6 O -0.0867(2) 0.6621(2) 0.0766(3) 0.0401(5) Uani 1 1 d . . .
O7 O 0.1316(3) 0.8029(2) 0.3234(2) 0.0434(6) Uani 1 1 d . . .
N1 N 0.4086(3) 0.3731(2) 0.0734(3) 0.0241(5) Uani 1 1 d . . .
N2 N 0.3959(3) 0.2413(2) -0.0237(3) 0.0273(5) Uani 1 1 d . A .
N3 N 0.4781(3) 0.6386(2) 0.2602(3) 0.0268(5) Uani 1 1 d . . .
C1 C 0.5351(3) 0.2395(3) -0.0148(4) 0.0308(7) Uani 1 1 d . . .
H1 H 0.5554 0.1596 -0.0701 0.037 Uiso 1 1 calc R A .
C2 C 0.6414(3) 0.3726(3) 0.0876(4) 0.0317(7) Uani 1 1 d . A .
H2 H 0.7474 0.4036 0.1160 0.038 Uiso 1 1 calc R . .
C3 C 0.5585(3) 0.4527(3) 0.1409(3) 0.0243(6) Uani 1 1 d . A .
C4 C 0.6007(3) 0.6022(3) 0.2516(3) 0.0265(6) Uani 1 1 d . A .
C5 C 0.7506(4) 0.6983(3) 0.3414(4) 0.0356(7) Uani 1 1 d . . .
H5 H 0.8344 0.6716 0.3326 0.043 Uiso 1 1 calc R A .
C6 C 0.7746(4) 0.8353(4) 0.4451(4) 0.0431(8) Uani 1 1 d . A .
H6 H 0.8757 0.9025 0.5090 0.052 Uiso 1 1 calc R . .
C7 C 0.6508(4) 0.8721(3) 0.4541(4) 0.0447(9) Uani 1 1 d . . .
H7 H 0.6657 0.9651 0.5232 0.054 Uiso 1 1 calc R A .
C8 C 0.5040(4) 0.7717(3) 0.3609(4) 0.0372(7) Uani 1 1 d . A .
H8 H 0.4191 0.7974 0.3680 0.045 Uiso 1 1 calc R . .
C9 C 0.2581(4) 0.1194(3) -0.0974(4) 0.0335(7) Uani 1 1 d . . .
H9A H 0.2463 0.0484 -0.1927 0.040 Uiso 1 1 calc R A .
H9B H 0.1654 0.1500 -0.1211 0.040 Uiso 1 1 calc R . .
C10 C 0.2712(4) 0.0523(3) 0.0045(4) 0.0378(8) Uani 1 1 d . A .
C11 C 0.1303(5) -0.1166(5) 0.0351(6) 0.0776(15) Uani 1 1 d . . .
H11A H 0.2020 -0.1713 0.0385 0.116 Uiso 1 1 calc R . .
H11B H 0.0251 -0.1811 -0.0133 0.116 Uiso 1 1 calc R . .
H11C H 0.1605 -0.0472 0.1373 0.116 Uiso 1 1 calc R . .
C12 C 0.2543(11) 0.3316(10) 0.3280(10) 0.060(2) Uiso 0.50 1 d P A 1
H12A H 0.3452 0.3051 0.3309 0.090 Uiso 0.50 1 calc PR A 1
H12B H 0.1642 0.2458 0.2715 0.090 Uiso 0.50 1 calc PR A 1
H12C H 0.2731 0.3839 0.4304 0.090 Uiso 0.50 1 calc PR A 1
C12A C 0.3259(14) 0.4041(13) 0.3805(13) 0.087(3) Uiso 0.50 1 d P A 2
H12D H 0.2664 0.3481 0.4046 0.130 Uiso 0.50 1 calc PR A 2
H12E H 0.3863 0.4988 0.4668 0.130 Uiso 0.50 1 calc PR A 2
H12F H 0.3960 0.3567 0.3567 0.130 Uiso 0.50 1 calc PR A 2
O8 O 0.1332(7) 0.8368(6) 0.5914(6) 0.0376(13) Uiso 0.50 1 d P B 1
H8A H 0.1386 0.8276 0.5134 0.045 Uiso 0.50 1 d PR B 1
C13 C 0.1564(13) 0.7263(12) 0.6241(13) 0.067(3) Uiso 0.50 1 d P B 1
H13A H 0.2617 0.7249 0.6486 0.101 Uiso 0.50 1 calc PR B 1
H13B H 0.0818 0.6361 0.5369 0.101 Uiso 0.50 1 calc PR B 1
H13C H 0.1421 0.7399 0.7098 0.101 Uiso 0.50 1 calc PR B 1
O8A O 0.1843(8) 0.8577(8) 0.6009(8) 0.065(2) Uiso 0.50 1 d P C 2
H8B H 0.1543 0.8327 0.5083 0.079 Uiso 0.50 1 d PR C 2
C13A C 0.2161(14) 0.7445(13) 0.6277(15) 0.084(4) Uiso 0.50 1 d P C 2
H13D H 0.2756 0.7049 0.5805 0.126 Uiso 0.50 1 calc PR C 2
H13E H 0.1188 0.6707 0.5853 0.126 Uiso 0.50 1 calc PR C 2
H13F H 0.2763 0.7786 0.7359 0.126 Uiso 0.50 1 calc PR C 2
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'
Cu Cu 0.3201 1.2651 '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'
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
O6 Cu1 O4 93.97(9) 2_565 .
O6 Cu1 N1 91.72(9) 2_565 .
O4 Cu1 N1 164.82(8) . .
O6 Cu1 N3 163.61(9) 2_565 .
O4 Cu1 N3 91.20(9) . .
N1 Cu1 N3 79.69(9) . .
O6 Cu1 O3 95.65(11) 2_565 .
O4 Cu1 O3 95.11(9) . .
N1 Cu1 O3 98.31(9) . .
N3 Cu1 O3 99.36(11) . .
O7 S1 O5 112.33(13) . .
O7 S1 O4 108.56(12) . .
O5 S1 O4 110.61(12) . .
O7 S1 O6 107.33(14) . .
O5 S1 O6 110.35(12) . .
O4 S1 O6 107.49(12) . .
C10 O1 C11 116.2(3) . .
C12A O3 C12 33.8(5) . .
C12A O3 Cu1 131.6(5) . .
C12 O3 Cu1 146.1(4) . .
C12A O3 H3A 121(3) . .
C12 O3 H3A 120(3) . .
Cu1 O3 H3A 93(3) . .
S1 O4 Cu1 134.75(12) . .
S1 O6 Cu1 133.74(13) . 2_565
C3 N1 N2 105.3(2) . .
C3 N1 Cu1 114.72(18) . .
N2 N1 Cu1 138.29(19) . .
C1 N2 N1 110.3(2) . .
C1 N2 C9 127.2(2) . .
N1 N2 C9 121.3(2) . .
C8 N3 C4 118.6(3) . .
C8 N3 Cu1 126.0(2) . .
C4 N3 Cu1 115.27(19) . .
N2 C1 C2 108.5(3) . .
N2 C1 H1 125.7 . .
C2 C1 H1 125.7 . .
C1 C2 C3 104.8(3) . .
C1 C2 H2 127.6 . .
C3 C2 H2 127.6 . .
N1 C3 C2 111.1(3) . .
N1 C3 C4 115.4(2) . .
C2 C3 C4 133.6(3) . .
N3 C4 C5 122.1(3) . .
N3 C4 C3 113.6(2) . .
C5 C4 C3 124.4(3) . .
C4 C5 C6 118.3(3) . .
C4 C5 H5 120.9 . .
C6 C5 H5 120.9 . .
C7 C6 C5 119.7(3) . .
C7 C6 H6 120.1 . .
C5 C6 H6 120.1 . .
C6 C7 C8 119.3(3) . .
C6 C7 H7 120.4 . .
C8 C7 H7 120.4 . .
N3 C8 C7 122.0(3) . .
N3 C8 H8 119.0 . .
C7 C8 H8 119.0 . .
N2 C9 C10 110.1(3) . .
N2 C9 H9A 109.6 . .
C10 C9 H9A 109.6 . .
N2 C9 H9B 109.6 . .
C10 C9 H9B 109.6 . .
H9A C9 H9B 108.2 . .
O2 C10 O1 124.9(3) . .
O2 C10 C9 125.0(3) . .
O1 C10 C9 110.0(3) . .
O1 C11 H11A 109.5 . .
O1 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
O1 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
O3 C12 H12A 109.5 . .
O3 C12 H12B 109.5 . .
O3 C12 H12C 109.5 . .
O3 C12A H12D 109.5 . .
O3 C12A H12E 109.5 . .
H12D C12A H12E 109.5 . .
O3 C12A H12F 109.5 . .
H12D C12A H12F 109.5 . .
H12E C12A H12F 109.5 . .
C13 O8 H8A 113.5 . .
C13 O8 H8B 113.3 . .
H8A O8 H8B 7.3 . .
C13A O8A H8A 107.0 . .
C13A O8A H8B 108.4 . .
H8A O8A H8B 12.8 . .
O8A C13A H13D 109.5 . .
O8A C13A H13E 109.5 . .
H13D C13A H13E 109.5 . .
O8A C13A H13F 109.5 . .
H13D C13A H13F 109.5 . .
H13E C13A H13F 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O6 1.930(2) 2_565
Cu1 O4 1.9376(19) .
Cu1 N1 2.008(2) .
Cu1 N3 2.022(2) .
Cu1 O3 2.207(2) .
S1 O7 1.453(2) .
S1 O5 1.455(2) .
S1 O4 1.4855(19) .
S1 O6 1.488(2) .
O1 C10 1.324(4) .
O1 C11 1.453(5) .
O2 C10 1.179(4) .
O3 C12A 1.359(11) .
O3 C12 1.366(9) .
O3 H3A 0.844(10) .
O6 Cu1 1.930(2) 2_565
N1 C3 1.342(3) .
N1 N2 1.356(3) .
N2 C1 1.349(4) .
N2 C9 1.444(3) .
N3 C8 1.340(4) .
N3 C4 1.350(4) .
C1 C2 1.361(4) .
C1 H1 0.9400 .
C2 C3 1.390(4) .
C2 H2 0.9400 .
C3 C4 1.466(4) .
C4 C5 1.379(4) .
C5 C6 1.386(5) .
C5 H5 0.9400 .
C6 C7 1.364(5) .
C6 H6 0.9400 .
C7 C8 1.375(4) .
C7 H7 0.9400 .
C8 H8 0.9400 .
C9 C10 1.515(4) .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C11 H11C 0.9700 .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C12 H12C 0.9700 .
C12A H12D 0.9700 .
C12A H12E 0.9700 .
C12A H12F 0.9700 .
O8 C13 1.373(12) .
O8 H8A 0.8500 .
O8 H8B 1.0050 .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C13 H13C 0.9700 .
O8A C13A 1.388(13) .
O8A H8A 0.7784 .
O8A H8B 0.8500 .
C13A H13D 0.9700 .
C13A H13E 0.9700 .
C13A H13F 0.9700 .
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_4
O6 Cu1 O3 C12A 137.8(7) 2_565 .
O4 Cu1 O3 C12A -127.7(7) . .
N1 Cu1 O3 C12A 45.2(7) . .
N3 Cu1 O3 C12A -35.6(7) . .
O6 Cu1 O3 C12 89.9(8) 2_565 .
O4 Cu1 O3 C12 -175.6(8) . .
N1 Cu1 O3 C12 -2.7(8) . .
N3 Cu1 O3 C12 -83.5(8) . .
O7 S1 O4 Cu1 117.66(19) . .
O5 S1 O4 Cu1 -6.0(2) . .
O6 S1 O4 Cu1 -126.54(17) . .
O6 Cu1 O4 S1 82.55(19) 2_565 .
N1 Cu1 O4 S1 -165.7(3) . .
N3 Cu1 O4 S1 -113.01(18) . .
O3 Cu1 O4 S1 -13.5(2) . .
O7 S1 O6 Cu1 -167.23(17) . 2_565
O5 S1 O6 Cu1 -44.5(2) . 2_565
O4 S1 O6 Cu1 76.2(2) . 2_565
O6 Cu1 N1 C3 155.07(19) 2_565 .
O4 Cu1 N1 C3 43.0(4) . .
N3 Cu1 N1 C3 -10.88(18) . .
O3 Cu1 N1 C3 -109.0(2) . .
O6 Cu1 N1 N2 -7.4(3) 2_565 .
O4 Cu1 N1 N2 -119.5(3) . .
N3 Cu1 N1 N2 -173.4(3) . .
O3 Cu1 N1 N2 88.6(3) . .
C3 N1 N2 C1 0.7(3) . .
Cu1 N1 N2 C1 164.2(2) . .
C3 N1 N2 C9 168.9(2) . .
Cu1 N1 N2 C9 -27.5(4) . .
O6 Cu1 N3 C8 125.8(3) 2_565 .
O4 Cu1 N3 C8 17.4(2) . .
N1 Cu1 N3 C8 -174.8(3) . .
O3 Cu1 N3 C8 -78.0(3) . .
O6 Cu1 N3 C4 -50.7(4) 2_565 .
O4 Cu1 N3 C4 -159.2(2) . .
N1 Cu1 N3 C4 8.6(2) . .
O3 Cu1 N3 C4 105.4(2) . .
N1 N2 C1 C2 -1.1(3) . .
C9 N2 C1 C2 -168.5(3) . .
N2 C1 C2 C3 1.0(3) . .
N2 N1 C3 C2 0.0(3) . .
Cu1 N1 C3 C2 -168.01(18) . .
N2 N1 C3 C4 179.5(2) . .
Cu1 N1 C3 C4 11.5(3) . .
C1 C2 C3 N1 -0.6(3) . .
C1 C2 C3 C4 -180.0(3) . .
C8 N3 C4 C5 -0.8(4) . .
Cu1 N3 C4 C5 176.0(2) . .
C8 N3 C4 C3 178.2(2) . .
Cu1 N3 C4 C3 -5.0(3) . .
N1 C3 C4 N3 -4.2(3) . .
C2 C3 C4 N3 175.1(3) . .
N1 C3 C4 C5 174.7(3) . .
C2 C3 C4 C5 -6.0(5) . .
N3 C4 C5 C6 1.1(4) . .
C3 C4 C5 C6 -177.8(3) . .
C4 C5 C6 C7 -1.0(5) . .
C5 C6 C7 C8 0.8(5) . .
C4 N3 C8 C7 0.5(5) . .
Cu1 N3 C8 C7 -175.9(2) . .
C6 C7 C8 N3 -0.5(5) . .
C1 N2 C9 C10 81.1(4) . .
N1 N2 C9 C10 -85.1(3) . .
C11 O1 C10 O2 1.1(5) . .
C11 O1 C10 C9 179.5(3) . .
N2 C9 C10 O2 -12.8(5) . .
N2 C9 C10 O1 168.8(2) . .
