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#$Date: 2018-08-12 06:27:56 +0300 (Sun, 12 Aug 2018) $
#$Revision: 209616 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/00/26/7002622.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_7002622
loop_
_publ_author_name
'Silva, Telma F. S.'
'Mishra, Gopal S.'
'Guedes da Silva, M. Fátima'
'Wanke, Riccardo'
'Martins, Luísa M. D. R. S.'
'Pombeiro, Armando J. L.'
_publ_section_title
;
 CuII complexes bearing the 2,2,2-tris(1-pyrazolyl)ethanol or
 2,2,2-tris(1-pyrazolyl)ethyl methanesulfonate scorpionates. X-Ray
 structural characterization and application in the mild catalytic
 peroxidative oxidation of cyclohexane
;
_journal_coden_ASTM              DTARAF
_journal_issue                   42
_journal_name_full               'Dalton Transactions'
_journal_page_first              9207
_journal_page_last               9215
_journal_paper_doi               10.1039/b911990f
_journal_year                    2009
_chemical_formula_moiety         'C11 H12 Cl2 Cu N6 O'
_chemical_formula_sum            'C11 H12 Cl2 Cu N6 O'
_chemical_formula_weight         378.71
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.902(5)
_cell_length_b                   13.026(5)
_cell_length_c                   16.7628(11)
_cell_measurement_reflns_used    4073
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.07
_cell_measurement_theta_min      2.43
_cell_volume                     3253.9(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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    'SIR97 (Giacovazzo et al, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17189
_diffrn_reflns_theta_full        28.77
_diffrn_reflns_theta_max         28.77
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    1.677
_exptl_absorpt_correction_T_max  0.8241
_exptl_absorpt_correction_T_min  0.7303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1528
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_platon_squeeze_details
;
;
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         4202
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.396
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0422
_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)+(0.0609P)²+0.7249P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1213
_reflns_number_gt                2966
_reflns_number_total             4202
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            B911990F.txt
_cod_data_source_block           compound3
_cod_original_cell_volume        3253.9(16)
_cod_database_code               7002622
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4687(2) 0.8076(3) 0.79688(19) 0.0228(7) Uani 1 1 d . . .
C2 C 0.4418(3) 0.8363(3) 0.8823(2) 0.0316(8) Uani 1 1 d . . .
H2A H 0.4634 0.7840 0.9187 0.038 Uiso 1 1 calc R . .
H2B H 0.4700 0.9008 0.8966 0.038 Uiso 1 1 calc R . .
C11 C 0.3964(3) 0.5855(3) 0.6962(3) 0.0405(10) Uani 1 1 d . . .
H11 H 0.3891 0.5454 0.6507 0.049 Uiso 1 1 calc R . .
C12 C 0.3689(3) 0.5567(3) 0.7718(3) 0.0440(11) Uani 1 1 d . . .
H12 H 0.3403 0.4961 0.7865 0.053 Uiso 1 1 calc R . .
C13 C 0.3928(3) 0.6361(3) 0.8199(3) 0.0348(9) Uani 1 1 d . . .
H13 H 0.3844 0.6395 0.8748 0.042 Uiso 1 1 calc R . .
C14 C 0.6918(3) 0.7753(3) 0.7370(2) 0.0349(9) Uani 1 1 d . . .
H14 H 0.7357 0.7595 0.6996 0.042 Uiso 1 1 calc R . .
C15 C 0.7093(3) 0.8021(3) 0.8153(3) 0.0375(9) Uani 1 1 d . . .
H15 H 0.7653 0.8077 0.8394 0.045 Uiso 1 1 calc R . .
C16 C 0.6288(3) 0.8183(3) 0.8495(2) 0.0302(8) Uani 1 1 d . . .
H16 H 0.6183 0.8371 0.9022 0.036 Uiso 1 1 calc R . .
C17 C 0.4192(3) 0.9609(3) 0.6296(2) 0.0346(9) Uani 1 1 d . . .
H17 H 0.4199 0.9749 0.5752 0.042 Uiso 1 1 calc R . .
C18 C 0.3831(3) 1.0251(3) 0.6861(2) 0.0370(9) Uani 1 1 d . . .
H18 H 0.3565 1.0888 0.6778 0.044 Uiso 1 1 calc R . .
C19 C 0.3945(3) 0.9755(3) 0.7568(2) 0.0312(8) Uani 1 1 d . . .
H19 H 0.3768 0.9993 0.8067 0.037 Uiso 1 1 calc R . .
N11 N 0.4342(2) 0.6773(2) 0.69692(18) 0.0322(7) Uani 1 1 d . . .
N13 N 0.4309(2) 0.7090(2) 0.77403(17) 0.0255(6) Uani 1 1 d . . .
N14 N 0.6046(2) 0.7749(3) 0.72218(17) 0.0287(7) Uani 1 1 d . . .
N16 N 0.5658(2) 0.8020(2) 0.79239(16) 0.0246(6) Uani 1 1 d . . .
N17 N 0.4527(2) 0.8772(2) 0.66194(17) 0.0272(7) Uani 1 1 d . . .
N19 N 0.4357(2) 0.8860(2) 0.74166(17) 0.0236(6) Uani 1 1 d . . .
O1 O 0.3482 0.8457 0.8904 0.0394(7) Uani 1 1 d D . .
Cl1 Cl 0.55733(9) 0.60643(8) 0.56010(6) 0.0445(3) Uani 1 1 d . . .
Cl2 Cl 0.57090(9) 0.84709(9) 0.51532(6) 0.0472(3) Uani 1 1 d . . .
Cu1 Cu 0.51331(3) 0.75326(3) 0.61710(2) 0.02816(16) Uani 1 1 d . . .
H1 H 0.3289 0.7993 0.9265 0.042 Uiso 1 1 d 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'
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'
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
N16 C1 N13 109.2(3) . . ?
N16 C1 N19 109.7(3) . . ?
N13 C1 N19 108.6(3) . . ?
N16 C1 C2 108.8(3) . . ?
N13 C1 C2 111.1(3) . . ?
N19 C1 C2 109.4(3) . . ?
O1 C2 C1 111.8 . . ?
O1 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
O1 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
N11 C11 C12 111.3(4) . . ?
N11 C11 H11 124.4 . . ?
C12 C11 H11 124.4 . . ?
C13 C12 C11 105.0(4) . . ?
C13 C12 H12 127.5 . . ?
C11 C12 H12 127.5 . . ?
N13 C13 C12 108.0(4) . . ?
N13 C13 H13 126.0 . . ?
C12 C13 H13 126.0 . . ?
N14 C14 C15 111.4(4) . . ?
N14 C14 H14 124.3 . . ?
C15 C14 H14 124.3 . . ?
C16 C15 C14 105.9(4) . . ?
C16 C15 H15 127.0 . . ?
C14 C15 H15 127.0 . . ?
C15 C16 N16 107.0(3) . . ?
C15 C16 H16 126.5 . . ?
N16 C16 H16 126.5 . . ?
N17 C17 C18 111.6(3) . . ?
N17 C17 H17 124.2 . . ?
C18 C17 H17 124.2 . . ?
C19 C18 C17 105.3(4) . . ?
C19 C18 H18 127.4 . . ?
C17 C18 H18 127.4 . . ?
N19 C19 C18 107.7(3) . . ?
N19 C19 H19 126.1 . . ?
C18 C19 H19 126.1 . . ?
C11 N11 N13 105.6(3) . . ?
C11 N11 Cu1 132.8(3) . . ?
N13 N11 Cu1 119.8(2) . . ?
C13 N13 N11 110.1(3) . . ?
C13 N13 C1 129.5(3) . . ?
N11 N13 C1 120.4(3) . . ?
C14 N14 N16 104.7(3) . . ?
C14 N14 Cu1 138.1(3) . . ?
N16 N14 Cu1 117.1(2) . . ?
C16 N16 N14 110.9(3) . . ?
C16 N16 C1 130.2(3) . . ?
N14 N16 C1 118.9(3) . . ?
C17 N17 N19 105.3(3) . . ?
C17 N17 Cu1 133.3(3) . . ?
N19 N17 Cu1 121.3(2) . . ?
C19 N19 N17 110.1(3) . . ?
C19 N19 C1 129.8(3) . . ?
N17 N19 C1 119.9(3) . . ?
C2 O1 H1 108.82 . . ?
N17 Cu1 N11 83.36(13) . . ?
N17 Cu1 Cl1 170.07(10) . . ?
N11 Cu1 Cl1 91.99(10) . . ?
N17 Cu1 N14 82.93(12) . . ?
N11 Cu1 N14 84.08(12) . . ?
Cl1 Cu1 N14 105.38(9) . . ?
N17 Cu1 Cl2 91.05(10) . . ?
N11 Cu1 Cl2 166.89(11) . . ?
Cl1 Cu1 Cl2 91.63(5) . . ?
N14 Cu1 Cl2 107.06(9) . . ?
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 N16 1.451(5) . ?
C1 N13 1.454(5) . ?
C1 N19 1.464(4) . ?
C1 C2 1.533(5) . ?
C2 O1 1.406 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C11 N11 1.321(5) . ?
C11 C12 1.383(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.359(6) . ?
C12 H12 0.9300 . ?
C13 N13 1.348(5) . ?
C13 H13 0.9300 . ?
C14 N14 1.322(5) . ?
C14 C15 1.383(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.347(6) . ?
C15 H15 0.9300 . ?
C16 N16 1.357(5) . ?
C16 H16 0.9300 . ?
C17 N17 1.316(5) . ?
C17 C18 1.374(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.360(5) . ?
C18 H18 0.9300 . ?
C19 N19 1.342(5) . ?
C19 H19 0.9300 . ?
N11 N13 1.358(4) . ?
N11 Cu1 2.040(3) . ?
N14 N16 1.358(4) . ?
N14 Cu1 2.244(3) . ?
N17 N19 1.365(4) . ?
N17 Cu1 1.997(3) . ?
O1 H1 0.90267 . ?
Cl1 Cu1 2.2364(12) . ?
Cl2 Cu1 2.2674(11) . ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.250 0.031 0.505 134.3 24.7
2 0.250 -0.010 1.005 134.3 25.0
3 0.750 0.030 0.995 134.3 24.9
4 0.750 -0.010 0.495 134.3 25.1
