#------------------------------------------------------------------------------
#$Date: 2016-03-25 23:46:43 +0200 (Fri, 25 Mar 2016) $
#$Revision: 180053 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/47/7034733.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_7034733
loop_
_publ_author_name
'Ording-Wenker, Erica C M'
'Siegler, Maxime A.'
'Lutz, Martin'
'Bouwman, Elisabeth'
_publ_section_title
;
 Catalytic catechol oxidation by copper complexes: development of a
 structure-activity relationship.
;
_journal_issue                   27
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              12196
_journal_page_last               12209
_journal_paper_doi               10.1039/c5dt01041a
_journal_volume                  44
_journal_year                    2015
_chemical_formula_moiety         'C15 H18 Cl Cu N3 S, Cl O4'
_chemical_formula_sum            'C15 H18 Cl2 Cu N3 O4 S'
_chemical_formula_weight         470.82
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-01-12 deposited with the CCDC.
2015-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.200(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.2487(5)
_cell_length_b                   12.6146(2)
_cell_length_c                   14.6206(4)
_cell_measurement_reflns_used    7421
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.63
_cell_volume                     3677.92(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics    'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Goniometer KM4/Xcalibur, detector: Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13583
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.250
_diffrn_reflns_theta_min         2.192
_exptl_absorpt_coefficient_mu    1.618
_exptl_absorpt_correction_T_max  0.836
_exptl_absorpt_correction_T_min  0.809
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_description       'small block'
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.868
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3708
_refine_ls_number_restraints     136
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0448P)²+7.6184P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0955
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3303
_reflns_number_total             3708
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5dt01041a2.cif
_cod_data_source_block           '[CuII2(L2SSL2)(Cl)2]n(ClO4)2n'
_cod_depositor_comments
'Adding full bibliography for 7034724--7034733.cif.'
_cod_database_code               7034733
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2013-2
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.48381(2) 0.87489(2) 0.05021(2) 0.02071(11) Uani 1 1 d . . . . .
Cl1 Cl 0.53924(3) 1.02236(5) 0.12367(5) 0.02702(16) Uani 1 1 d . . . . .
S1 S 0.52776(3) 0.73528(5) 0.20542(5) 0.02590(16) Uani 1 1 d . . . . .
C1 C 0.42060(14) 0.6656(2) 0.0441(2) 0.0267(6) Uani 1 1 d . . . . .
H1A H 0.3990 0.6030 0.0048 0.032 Uiso 1 1 calc R U . . .
H1B H 0.3908 0.6907 0.0787 0.032 Uiso 1 1 calc R U . . .
C2 C 0.48647(15) 0.6313(2) 0.1188(2) 0.0289(6) Uani 1 1 d . . . . .
H2A H 0.5169 0.6080 0.0845 0.035 Uiso 1 1 calc R U . . .
H2B H 0.4783 0.5697 0.1552 0.035 Uiso 1 1 calc R U . . .
C12 C 0.53200(14) 0.7256(2) -0.0553(2) 0.0271(6) Uani 1 1 d . . . . .
C13 C 0.57020(17) 0.6698(2) -0.0992(3) 0.0368(7) Uani 1 1 d . . . . .
H13 H 0.5495 0.6254 -0.1539 0.044 Uiso 1 1 calc R U . . .
C14 C 0.63920(18) 0.6803(3) -0.0613(3) 0.0430(8) Uani 1 1 d . . . . .
H14 H 0.6669 0.6453 -0.0909 0.052 Uiso 1 1 calc R U . . .
C15 C 0.66650(15) 0.7415(3) 0.0186(3) 0.0413(8) Uani 1 1 d . . . . .
H15 H 0.7139 0.7471 0.0466 0.050 Uiso 1 1 calc R U . . .
C16 C 0.62616(14) 0.7973(2) 0.0611(2) 0.0313(6) Uani 1 1 d . . . . .
C17 C 0.45716(14) 0.7137(2) -0.0946(2) 0.0282(6) Uani 1 1 d . . . . .
H17A H 0.4387 0.7546 -0.1559 0.034 Uiso 1 1 calc R U . . .
H17B H 0.4456 0.6382 -0.1098 0.034 Uiso 1 1 calc R U . . .
C18 C 0.65903(16) 0.8564(3) 0.1505(3) 0.0434(8) Uani 1 1 d . . . . .
H18A H 0.6691 0.9283 0.1342 0.065 Uiso 1 1 calc R U . . .
H18B H 0.7008 0.8207 0.1885 0.065 Uiso 1 1 calc R U . . .
H18C H 0.6293 0.8601 0.1888 0.065 Uiso 1 1 calc R U . . .
C22 C 0.34143(14) 0.8709(2) -0.0054(2) 0.0267(6) Uani 1 1 d . . . . .
C23 C 0.27667(15) 0.8924(2) -0.0081(2) 0.0353(7) Uani 1 1 d . . . . .
H23 H 0.2391 0.8586 -0.0542 0.042 Uiso 1 1 calc R U . . .
C24 C 0.26828(17) 0.9654(3) 0.0590(3) 0.0396(8) Uani 1 1 d . . . . .
H24 H 0.2245 0.9819 0.0582 0.048 Uiso 1 1 calc R U . . .
C25 C 0.32297(17) 1.0135(3) 0.1261(3) 0.0380(7) Uani 1 1 d . . . . .
H25 H 0.3176 1.0618 0.1727 0.046 Uiso 1 1 calc R U . . .
C26 C 0.38559(17) 0.9896(2) 0.1239(2) 0.0339(7) Uani 1 1 d . . . . .
H26 H 0.4237 1.0229 0.1693 0.041 Uiso 1 1 calc R U . . .
C27 C 0.35805(13) 0.7972(2) -0.0742(2) 0.0272(6) Uani 1 1 d . . . . .
H27A H 0.3573 0.8363 -0.1333 0.033 Uiso 1 1 calc R U . . .
H27B H 0.3244 0.7396 -0.0942 0.033 Uiso 1 1 calc R U . . .
N1 N 0.42641(11) 0.75157(17) -0.02381(17) 0.0233(5) Uani 1 1 d . . . . .
N11 N 0.55861(11) 0.79131(17) 0.02057(17) 0.0241(5) Uani 1 1 d . . . . .
N21 N 0.39450(11) 0.92011(18) 0.05901(17) 0.0250(5) Uani 1 1 d . . . . .
Cl2 Cl 0.3287(8) 0.4934(11) -0.2393(14) 0.035(2) Uani 0.34(4) 1 d D U P A 1
O1 O 0.2703(10) 0.4275(18) -0.257(2) 0.036(3) Uani 0.34(4) 1 d D U P A 1
O2 O 0.3628(10) 0.4673(19) -0.3049(17) 0.028(3) Uani 0.34(4) 1 d D U P A 1
O3 O 0.3042(15) 0.6006(13) -0.254(2) 0.056(4) Uani 0.34(4) 1 d D U P A 1
O4 O 0.3701(13) 0.482(2) -0.1395(16) 0.039(4) Uani 0.34(4) 1 d D U P A 1
Cl2' Cl 0.3344(3) 0.4901(5) -0.2264(7) 0.0250(9) Uani 0.66(4) 1 d D U P A 2
O1' O 0.2771(7) 0.4237(12) -0.2616(13) 0.058(3) Uani 0.66(4) 1 d D U P A 2
O2' O 0.3756(7) 0.4776(13) -0.2856(11) 0.041(2) Uani 0.66(4) 1 d D U P A 2
O3' O 0.3176(4) 0.6003(6) -0.2283(10) 0.039(2) Uani 0.66(4) 1 d D U P A 2
O4' O 0.3735(6) 0.4607(11) -0.1274(8) 0.0345(19) Uani 0.66(4) 1 d D U P A 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'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 '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
N21 Cu1 N1 81.20(9) . .
N21 Cu1 N11 163.29(9) . .
N1 Cu1 N11 82.10(9) . .
N21 Cu1 Cl1 94.80(7) . .
N1 Cu1 Cl1 174.37(7) . .
N11 Cu1 Cl1 101.90(6) . .
N21 Cu1 Cl1 93.12(7) . 5_675
N1 Cu1 Cl1 89.20(7) . 5_675
N11 Cu1 Cl1 87.19(7) . 5_675
Cl1 Cu1 Cl1 87.05(2) . 5_675
N21 Cu1 S1 100.67(7) . .
N1 Cu1 S1 85.43(7) . .
N11 Cu1 S1 77.40(7) . .
Cl1 Cu1 S1 99.26(3) . .
Cl1 Cu1 S1 164.24(2) 5_675 .
Cu1 Cl1 Cu1 92.95(2) . 5_675
C2 S1 S1 101.43(10) . 2_655
C2 S1 Cu1 86.74(10) . .
S1 S1 Cu1 114.75(3) 2_655 .
N1 C1 C2 114.6(2) . .
N1 C1 H1A 108.6 . .
C2 C1 H1A 108.6 . .
N1 C1 H1B 108.6 . .
C2 C1 H1B 108.6 . .
H1A C1 H1B 107.6 . .
C1 C2 S1 113.56(18) . .
C1 C2 H2A 108.9 . .
S1 C2 H2A 108.9 . .
C1 C2 H2B 108.9 . .
S1 C2 H2B 108.9 . .
H2A C2 H2B 107.7 . .
N11 C12 C13 123.3(3) . .
N11 C12 C17 117.8(2) . .
C13 C12 C17 119.0(3) . .
C14 C13 C12 118.3(3) . .
C14 C13 H13 120.8 . .
C12 C13 H13 120.8 . .
C15 C14 C13 118.7(3) . .
C15 C14 H14 120.7 . .
C13 C14 H14 120.7 . .
C14 C15 C16 121.4(3) . .
C14 C15 H15 119.3 . .
C16 C15 H15 119.3 . .
N11 C16 C15 119.6(3) . .
N11 C16 C18 121.9(3) . .
C15 C16 C18 118.4(3) . .
N1 C17 C12 111.4(2) . .
N1 C17 H17A 109.3 . .
C12 C17 H17A 109.3 . .
N1 C17 H17B 109.3 . .
C12 C17 H17B 109.3 . .
H17A C17 H17B 108.0 . .
C16 C18 H18A 109.5 . .
C16 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C16 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
N21 C22 C23 120.8(3) . .
N21 C22 C27 114.9(2) . .
C23 C22 C27 124.3(3) . .
C22 C23 C24 118.2(3) . .
C22 C23 H23 120.9 . .
C24 C23 H23 120.9 . .
C25 C24 C23 120.6(3) . .
C25 C24 H24 119.7 . .
C23 C24 H24 119.7 . .
C26 C25 C24 118.2(3) . .
C26 C25 H25 120.9 . .
C24 C25 H25 120.9 . .
N21 C26 C25 122.0(3) . .
N21 C26 H26 119.0 . .
C25 C26 H26 119.0 . .
C22 C27 N1 108.8(2) . .
C22 C27 H27A 109.9 . .
N1 C27 H27A 109.9 . .
C22 C27 H27B 109.9 . .
N1 C27 H27B 109.9 . .
H27A C27 H27B 108.3 . .
C17 N1 C27 111.6(2) . .
C17 N1 C1 112.6(2) . .
C27 N1 C1 108.4(2) . .
C17 N1 Cu1 106.82(16) . .
C27 N1 Cu1 105.54(16) . .
C1 N1 Cu1 111.72(17) . .
C12 N11 C16 118.5(2) . .
C12 N11 Cu1 110.60(17) . .
C16 N11 Cu1 130.8(2) . .
C22 N21 C26 120.2(2) . .
C22 N21 Cu1 113.72(18) . .
C26 N21 Cu1 126.0(2) . .
O2 Cl2 O4 112.7(14) . .
O2 Cl2 O3 111.2(14) . .
O4 Cl2 O3 108.0(13) . .
O2 Cl2 O1 110.5(13) . .
O4 Cl2 O1 108.4(14) . .
O3 Cl2 O1 105.7(14) . .
O1' Cl2' O3' 112.9(8) . .
O1' Cl2' O2' 110.0(7) . .
O3' Cl2' O2' 107.1(7) . .
O1' Cl2' O4' 109.7(8) . .
O3' Cl2' O4' 108.8(6) . .
O2' Cl2' O4' 108.3(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N21 2.028(2) .
Cu1 N1 2.041(2) .
Cu1 N11 2.074(2) .
Cu1 Cl1 2.2644(7) .
Cu1 Cl1 2.7428(8) 5_675
Cu1 S1 2.7676(7) .
Cl1 Cu1 2.7428(8) 5_675
S1 C2 1.824(3) .
S1 S1 2.0378(13) 2_655
C1 N1 1.504(3) .
C1 C2 1.511(4) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C12 N11 1.344(4) .
C12 C13 1.388(4) .
C12 C17 1.500(4) .
C13 C14 1.383(5) .
C13 H13 0.9500 .
C14 C15 1.353(5) .
C14 H14 0.9500 .
C15 C16 1.409(4) .
C15 H15 0.9500 .
C16 N11 1.353(4) .
C16 C18 1.457(5) .
C17 N1 1.481(3) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C22 N21 1.346(4) .
C22 C23 1.390(4) .
C22 C27 1.498(4) .
C23 C24 1.401(5) .
C23 H23 0.9500 .
C24 C25 1.376(5) .
C24 H24 0.9500 .
C25 C26 1.375(4) .
C25 H25 0.9500 .
C26 N21 1.352(4) .
C26 H26 0.9500 .
C27 N1 1.498(3) .
C27 H27A 0.9900 .
C27 H27B 0.9900 .
Cl2 O2 1.426(12) .
Cl2 O4 1.427(12) .
Cl2 O3 1.439(12) .
Cl2 O1 1.440(12) .
Cl2' O1' 1.419(7) .
Cl2' O3' 1.434(6) .
Cl2' O2' 1.439(7) .
Cl2' O4' 1.446(7) .
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
N1 C1 C2 S1 64.7(3) .
S1 S1 C2 C1 76.3(2) 2_655
Cu1 S1 C2 C1 -38.30(19) .
N11 C12 C13 C14 1.7(5) .
C17 C12 C13 C14 -179.1(3) .
C12 C13 C14 C15 2.2(5) .
C13 C14 C15 C16 -2.4(5) .
C14 C15 C16 N11 -1.2(5) .
C14 C15 C16 C18 176.3(3) .
N11 C12 C17 N1 -17.6(3) .
C13 C12 C17 N1 163.1(3) .
N21 C22 C23 C24 -1.0(4) .
C27 C22 C23 C24 -178.2(3) .
C22 C23 C24 C25 -0.6(4) .
C23 C24 C25 C26 1.4(5) .
C24 C25 C26 N21 -0.8(5) .
N21 C22 C27 N1 30.8(3) .
C23 C22 C27 N1 -151.9(3) .
C12 C17 N1 C27 148.1(2) .
C12 C17 N1 C1 -89.8(3) .
C12 C17 N1 Cu1 33.2(3) .
C22 C27 N1 C17 -157.6(2) .
C22 C27 N1 C1 77.9(3) .
C22 C27 N1 Cu1 -41.9(2) .
C2 C1 N1 C17 71.3(3) .
C2 C1 N1 C27 -164.8(2) .
C2 C1 N1 Cu1 -49.0(3) .
C13 C12 N11 C16 -5.3(4) .
C17 C12 N11 C16 175.5(2) .
C13 C12 N11 Cu1 171.6(2) .
C17 C12 N11 Cu1 -7.7(3) .
C15 C16 N11 C12 4.9(4) .
C18 C16 N11 C12 -172.5(3) .
C15 C16 N11 Cu1 -171.2(2) .
C18 C16 N11 Cu1 11.4(4) .
C23 C22 N21 C26 1.7(4) .
C27 C22 N21 C26 179.1(2) .
C23 C22 N21 Cu1 179.4(2) .
C27 C22 N21 Cu1 -3.1(3) .
C25 C26 N21 C22 -0.8(4) .
C25 C26 N21 Cu1 -178.2(2) .
