#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:59:43 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179874 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/70/7017002.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_7017002
loop_
_publ_author_name
'Zats, Galina M.'
'Arora, Himanshu'
'Lavi, Ronit'
'Yufit, Dmitry'
'Benisvy, Laurent'
_publ_section_title
;
 Phenolate and phenoxyl radical complexes of Cu(ii) and Co(iii), bearing a
 new redox active N,O-phenol-pyrazole ligand.
;
_journal_issue                   41
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              10889
_journal_page_last               10896
_journal_paper_doi               10.1039/c1dt10615e
_journal_volume                  40
_journal_year                    2011
_chemical_formula_moiety         '2(C18 H25 Cu0.5 N2 O)'
_chemical_formula_sum            'C36 H50 Cu N4 O2'
_chemical_formula_weight         634.34
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.830(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   17.3973(5)
_cell_length_b                   10.2763(3)
_cell_length_c                   9.3303(3)
_cell_measurement_reflns_used    4602
_cell_measurement_temperature    120
_cell_measurement_theta_max      31.071
_cell_measurement_theta_min      2.302
_cell_volume                     1667.22(9)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics
;
OLEX2: a complete structure solution, refinement and analysis program.
Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material
;
OLEX2: a complete structure solution, refinement and analysis program.
Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
A short history of SHELX (Sheldrick, 2007)/Bruker
;
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       '/w scans'
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0766
_diffrn_reflns_av_sigmaI/netI    0.0556
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19992
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             678
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.964
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4422
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.943
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0479
_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)+(0.0700P)²+1.0000P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1312
_reflns_number_gt                3096
_reflns_number_total             4422
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1dt10615e.txt
_cod_data_source_block           2_DBL10
_cod_database_code               7017002
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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
Cu1 Cu 1.0000 0.5000 0.5000 0.01923(12) Uani 1 2 d S . .
O1 O 0.89469(8) 0.50455(15) 0.55655(16) 0.0210(3) Uani 1 1 d . . .
N1 N 0.96678(10) 0.45260(19) 0.3101(2) 0.0219(4) Uani 1 1 d . . .
N2 N 1.01863(11) 0.42051(19) 0.2105(2) 0.0228(4) Uani 1 1 d . . .
C1 C 0.98481(13) 0.3592(2) 0.0983(2) 0.0230(4) Uani 1 1 d . . .
C2 C 0.90783(13) 0.3503(2) 0.1257(2) 0.0240(5) Uani 1 1 d . . .
C3 C 0.89835(12) 0.4113(2) 0.2603(2) 0.0222(4) Uani 1 1 d . . .
C4 C 0.82758(12) 0.4359(2) 0.3386(2) 0.0219(4) Uani 1 1 d . . .
C5 C 0.82954(12) 0.4856(2) 0.4811(2) 0.0214(4) Uani 1 1 d . . .
C6 C 0.75716(12) 0.5127(2) 0.5440(2) 0.0218(4) Uani 1 1 d . . .
C7 C 0.69028(13) 0.4910(2) 0.4641(3) 0.0244(4) Uani 1 1 d . . .
C8 C 0.68758(12) 0.4407(2) 0.3241(3) 0.0254(5) Uani 1 1 d . A .
C9 C 0.75736(13) 0.4145(2) 0.2644(2) 0.0241(5) Uani 1 1 d . . .
C10 C 0.61117(13) 0.4203(3) 0.2409(3) 0.0310(5) Uani 1 1 d . . .
C11 C 0.6148(3) 0.4986(5) 0.0990(5) 0.0416(10) Uiso 0.60 1 d P A 1
H11A H 0.5682 0.4856 0.0432 0.062 Uiso 0.60 1 calc PR A 1
H11C H 0.6578 0.4692 0.0456 0.062 Uiso 0.60 1 calc PR A 1
H11B H 0.6209 0.5895 0.1205 0.062 Uiso 0.60 1 calc PR A 1
C11A C 0.6189(4) 0.3525(7) 0.0927(7) 0.0373(15) Uiso 0.40 1 d P A 2
H11D H 0.5690 0.3451 0.0463 0.056 Uiso 0.40 1 calc PR A 2
H11E H 0.6406 0.2674 0.1064 0.056 Uiso 0.40 1 calc PR A 2
H11F H 0.6518 0.4034 0.0340 0.056 Uiso 0.40 1 calc PR A 2
C12 C 0.6030(3) 0.2791(6) 0.2076(6) 0.0566(14) Uiso 0.60 1 d P A 1
H12B H 0.6013 0.2305 0.2954 0.085 Uiso 0.60 1 calc PR A 1
H12C H 0.6461 0.2508 0.1539 0.085 Uiso 0.60 1 calc PR A 1
H12A H 0.5564 0.2649 0.1521 0.085 Uiso 0.60 1 calc PR A 1
C12A C 0.5582(4) 0.3249(7) 0.3272(8) 0.0388(15) Uiso 0.40 1 d P A 2
H12F H 0.5490 0.3612 0.4199 0.058 Uiso 0.40 1 calc PR A 2
H12E H 0.5833 0.2422 0.3386 0.058 Uiso 0.40 1 calc PR A 2
H12D H 0.5101 0.3134 0.2755 0.058 Uiso 0.40 1 calc PR A 2
C13 C 0.5427(3) 0.4703(5) 0.3206(6) 0.0513(13) Uiso 0.60 1 d P A 1
H13A H 0.4969 0.4602 0.2615 0.077 Uiso 0.60 1 calc PR A 1
H13C H 0.5501 0.5607 0.3431 0.077 Uiso 0.60 1 calc PR A 1
H13B H 0.5377 0.4217 0.4077 0.077 Uiso 0.60 1 calc PR A 1
C13A C 0.5679(4) 0.5469(8) 0.2217(8) 0.0423(16) Uiso 0.40 1 d P A 2
H13D H 0.5191 0.5305 0.1742 0.063 Uiso 0.40 1 calc PR A 2
H13F H 0.5972 0.6055 0.1649 0.063 Uiso 0.40 1 calc PR A 2
H13E H 0.5598 0.5852 0.3139 0.063 Uiso 0.40 1 calc PR A 2
C14 C 0.75405(13) 0.5688(2) 0.6970(2) 0.0254(5) Uani 1 1 d . . .
C15 C 0.67125(14) 0.5939(3) 0.7423(3) 0.0333(6) Uani 1 1 d . . .
C16 C 0.78908(15) 0.4709(3) 0.8057(3) 0.0297(5) Uani 1 1 d . . .
C17 C 0.79504(15) 0.7015(3) 0.7061(3) 0.0305(5) Uani 1 1 d . . .
C18 C 1.03140(15) 0.3153(2) -0.0244(3) 0.0277(5) Uani 1 1 d . . .
H2 H 1.0656(16) 0.436(3) 0.229(3) 0.024(7) Uiso 1 1 d . . .
H2A H 0.8706(16) 0.304(3) 0.067(3) 0.039(8) Uiso 1 1 d . . .
H7 H 0.6476(17) 0.512(2) 0.501(3) 0.029(8) Uiso 1 1 d . . .
H9 H 0.7589(15) 0.385(3) 0.169(3) 0.028(7) Uiso 1 1 d . . .
H15A H 0.6406(19) 0.513(3) 0.749(3) 0.036(8) Uiso 1 1 d . . .
H15B H 0.6464(18) 0.660(3) 0.684(3) 0.044(9) Uiso 1 1 d . . .
H15C H 0.6716(17) 0.628(3) 0.832(4) 0.044(9) Uiso 1 1 d . . .
H16A H 0.7544(18) 0.396(3) 0.817(3) 0.039(8) Uiso 1 1 d . . .
H16B H 0.8358(18) 0.443(3) 0.776(3) 0.038(8) Uiso 1 1 d . . .
H16C H 0.7977(19) 0.509(3) 0.896(4) 0.039(8) Uiso 1 1 d . . .
H17A H 0.7655(17) 0.767(3) 0.645(3) 0.040(8) Uiso 1 1 d . . .
H17B H 0.7978(16) 0.735(3) 0.803(3) 0.034(7) Uiso 1 1 d . . .
H17C H 0.8466(16) 0.697(3) 0.678(3) 0.027(7) Uiso 1 1 d . . .
H18A H 1.0007(16) 0.301(3) -0.106(3) 0.033(7) Uiso 1 1 d . . .
H18B H 1.0610(15) 0.241(3) -0.002(3) 0.028(7) Uiso 1 1 d . . .
H18C H 1.0634(14) 0.378(3) -0.053(3) 0.020(6) Uiso 1 1 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'
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
O1 Cu1 O1 180.0 . 3_766
O1 C5 C4 122.79(19) . .
O1 C5 C6 120.0(2) . .
N1 Cu1 O1 89.89(7) 3_766 3_766
N1 Cu1 O1 89.89(7) . .
N1 Cu1 O1 90.11(7) . 3_766
N1 Cu1 O1 90.11(7) 3_766 .
N1 Cu1 N1 179.999(1) . 3_766
N1 N2 H2 118.3(18) . .
N1 C3 C2 108.76(19) . .
N1 C3 C4 121.5(2) . .
N2 N1 Cu1 120.64(14) . .
N2 C1 C2 106.93(19) . .
N2 C1 C18 120.3(2) . .
C1 N2 N1 111.37(19) . .
C1 N2 H2 130.1(18) . .
C1 C2 C3 106.1(2) . .
C1 C2 H2A 124.7(17) . .
C1 C18 H18A 111.3(17) . .
C1 C18 H18B 112.5(15) . .
C1 C18 H18C 111.3(16) . .
C2 C1 C18 132.7(2) . .
C2 C3 C4 129.6(2) . .
C3 N1 Cu1 130.18(15) . .
C3 N1 N2 106.84(18) . .
C3 C2 H2A 128.9(17) . .
C4 C5 C6 117.2(2) . .
C4 C9 H9 117.9(16) . .
C5 O1 Cu1 130.91(14) . .
C5 C4 C3 122.0(2) . .
C5 C6 C14 120.6(2) . .
C6 C7 C8 124.4(2) . .
C6 C7 H7 118(2) . .
C7 C6 C5 119.0(2) . .
C7 C6 C14 120.44(19) . .
C7 C8 C10 121.6(2) . .
C8 C7 H7 118(2) . .
C8 C9 C4 122.3(2) . .
C8 C9 H9 119.7(16) . .
C8 C10 C11 107.6(3) . .
C8 C10 C11A 114.4(3) . .
C8 C10 C12A 109.7(3) . .
C9 C4 C3 117.2(2) . .
C9 C4 C5 120.8(2) . .
C9 C8 C7 116.4(2) . .
C9 C8 C10 122.0(2) . .
C10 C11 H11A 109.5 . .
C10 C11 H11C 109.5 . .
C10 C11 H11B 109.5 . .
C10 C11A H11D 109.5 . .
C10 C11A H11E 109.5 . .
C10 C11A H11F 109.5 . .
C10 C12 H12B 109.5 . .
C10 C12 H12C 109.5 . .
C10 C12 H12A 109.5 . .
C10 C12A H12F 109.5 . .
C10 C12A H12E 109.5 . .
C10 C12A H12D 109.5 . .
C10 C13 H13A 109.5 . .
C10 C13 H13C 109.5 . .
C10 C13 H13B 109.5 . .
C10 C13A H13D 109.5 . .
C10 C13A H13F 109.5 . .
C10 C13A H13E 109.5 . .
C11 C10 C11A 57.8(3) . .
C11 C10 C12A 142.7(4) . .
C11A C10 C12A 104.1(4) . .
H11D C11A H11E 109.5 . .
H11D C11A H11F 109.5 . .
H11E C11A H11F 109.5 . .
C12 C10 C8 108.3(3) . .
C12 C10 C11 109.5(3) . .
C12 C10 C11A 52.4(3) . .
C12 C10 C12A 56.6(3) . .
C12 C10 C13 111.2(4) . .
C12 C10 C13A 140.4(4) . .
H12F C12A H12E 109.5 . .
H12F C12A H12D 109.5 . .
H12E C12A H12D 109.5 . .
C13 C10 C8 112.8(3) . .
C13 C10 C11 107.3(3) . .
C13 C10 C11A 132.8(4) . .
C13 C10 C12A 58.7(3) . .
C13A C10 C8 111.3(4) . .
C13A C10 C11 59.1(3) . .
C13A C10 C11A 109.6(4) . .
C13A C10 C12A 107.3(4) . .
C13A C10 C13 50.9(4) . .
H13D C13A H13F 109.5 . .
H13D C13A H13E 109.5 . .
H13F C13A H13E 109.5 . .
C14 C15 H15A 113.0(18) . .
C14 C15 H15B 111.8(18) . .
C14 C15 H15C 110(2) . .
C14 C16 H16A 110.4(18) . .
C14 C16 H16B 110.0(19) . .
C14 C16 H16C 111.6(18) . .
C14 C17 H17A 109.6(17) . .
C14 C17 H17B 111.8(17) . .
C14 C17 H17C 112.7(16) . .
C15 C14 C6 112.2(2) . .
C15 C14 C16 106.5(2) . .
C15 C14 C17 105.8(2) . .
C16 C14 C6 109.93(19) . .
C16 C14 C17 111.7(2) . .
C17 C14 C6 110.61(19) . .
H15A C15 H15B 113(3) . .
H15A C15 H15C 104(3) . .
H15B C15 H15C 104(3) . .
H16A C16 H16B 110(3) . .
H16A C16 H16C 108(2) . .
H16B C16 H16C 107(3) . .
H17A C17 H17B 108(2) . .
H17A C17 H17C 110(2) . .
H17B C17 H17C 105(2) . .
H18A C18 H18B 111(2) . .
H18A C18 H18C 103(2) . .
H18B C18 H18C 108(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.9233(14) .
Cu1 O1 1.9233(14) 3_766
Cu1 N1 1.9092(19) .
Cu1 N1 1.9093(19) 3_766
O1 C5 1.329(3) .
N1 N2 1.356(2) .
N1 C3 1.334(3) .
N2 C1 1.342(3) .
N2 H2 0.84(3) .
C1 C2 1.374(3) .
C1 C18 1.493(3) .
C2 C3 1.418(3) .
C2 H2A 0.96(3) .
C3 C4 1.474(3) .
C4 C5 1.424(3) .
C4 C9 1.402(3) .
C5 C6 1.433(3) .
C6 C7 1.380(3) .
C6 C14 1.542(3) .
C7 C8 1.404(3) .
C7 H7 0.86(3) .
C8 C9 1.378(3) .
C8 C10 1.532(3) .
C9 H9 0.95(3) .
C10 C11 1.553(5) .
C10 C11A 1.558(7) .
C10 C12 1.489(6) .
C10 C12A 1.583(7) .
C10 C13 1.514(6) .
C10 C13A 1.512(8) .
C11 H11A 0.9600 .
C11 H11C 0.9600 .
C11 H11B 0.9600 .
C11A H11D 0.9600 .
C11A H11E 0.9600 .
C11A H11F 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C12 H12A 0.9600 .
C12A H12F 0.9600 .
C12A H12E 0.9600 .
C12A H12D 0.9600 .
C13 H13A 0.9600 .
C13 H13C 0.9600 .
C13 H13B 0.9600 .
C13A H13D 0.9600 .
C13A H13F 0.9600 .
C13A H13E 0.9600 .
C14 C15 1.536(3) .
C14 C16 1.540(3) .
C14 C17 1.541(3) .
C15 H15A 0.99(3) .
C15 H15B 0.97(3) .
C15 H15C 0.91(3) .
C16 H16A 0.98(3) .
C16 H16B 0.91(3) .
C16 H16C 0.94(3) .
C17 H17A 1.01(3) .
C17 H17B 0.97(3) .
C17 H17C 0.94(3) .
C18 H18A 0.93(3) .
C18 H18B 0.94(3) .
C18 H18C 0.90(3) .
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
N2 H2 O1 0.84(3) 2.18(3) 2.717(2) 121(2) 3_766
