#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/60/2016020.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2016020
loop_
_publ_author_name
'García, Ana María'
'Manzur, Jorge'
'Vega, Andrés'
_publ_section_title
;Di-μ-hydroxido-bis{[bis(6-methyl-2-pyridylmethyl)(2-phenylethyl)amine-κ³N',N'',N''']copper(II)}
 bis(perchlorate)
;
_journal_coeditor_code           BG3038
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m335
_journal_page_last               m337
_journal_paper_doi               10.1107/S0108270107025929
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Cu2 (O H)2 (C22 H25 N3)2] (Cl O4)2'
_chemical_formula_moiety         'C44 H52 Cu2 N6 O2 2+ , 2Cl O4 -'
_chemical_formula_sum            'C44 H52 Cl2 Cu2 N6 O10'
_chemical_formula_weight         1022.92
_chemical_name_systematic
;
Di-μ-hydroxo-bis{[bis(6-methyl-2-pyridylmethyl)(2-phenylethyl)amine-
κ³N',N'',N''']copper(II)} bis(perchlorate)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.229(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.9239(11)
_cell_length_b                   16.5696(19)
_cell_length_c                   13.9248(16)
_cell_measurement_reflns_used    2100
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      19.531
_cell_measurement_theta_min      2.792
_cell_volume                     2229.0(4)
_computing_cell_refinement       'SAINT-NT (Bruker, 1999)'
_computing_data_collection       'SMART-NT (Bruker, 2001)'
_computing_data_reduction        SAINT-NT
_computing_molecular_graphics    SHELXTL-NT
_computing_publication_material  SHELXTL-NT
_computing_structure_refinement  SHELXTL-NT
_computing_structure_solution    'SHELXTL-NT (Bruker, 1999)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0517
_diffrn_reflns_av_sigmaI/netI    0.0526
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13767
_diffrn_reflns_theta_full        25.21
_diffrn_reflns_theta_max         25.21
_diffrn_reflns_theta_min         1.94
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.139
_exptl_absorpt_correction_T_max  0.8660
_exptl_absorpt_correction_T_min  0.6524
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   '(SADABS in SAINT-NT; Bruker, 1999)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1060
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.313
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         3964
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0514
_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)+(0.0811P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1366
_reflns_number_gt                2909
_reflns_number_total             3964
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bg3038.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2016020
_cod_database_fobs_code          2016020
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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
Cu Cu1 0.39102(4) 0.53606(3) 0.41763(3) 0.03802(18) Uani d . 1 . .
O O1 0.4145(2) 0.49178(16) 0.54868(17) 0.0440(6) Uani d . 1 . .
H H1 0.3788 0.5043 0.5990 0.054(12) Uiso d . 1 . .
N N1 0.1913(3) 0.5678(2) 0.4137(2) 0.0461(7) Uani d . 1 . .
C C1 0.1483(4) 0.4308(3) 0.3506(3) 0.0602(11) Uani d . 1 . .
H H1A 0.1615 0.3951 0.4073 0.072 Uiso calc R 1 . .
H H1B 0.0787 0.4068 0.2980 0.072 Uiso calc R 1 . .
C C2 0.0963(4) 0.5114(3) 0.3776(3) 0.0543(10) Uani d . 1 . .
C C3 -0.0417(4) 0.5234(3) 0.3715(4) 0.0739(14) Uani d . 1 . .
H H3 -0.1056 0.4835 0.3455 0.089 Uiso calc R 1 . .
C C4 -0.0847(5) 0.5946(4) 0.4039(4) 0.0788(15) Uani d . 1 . .
H H4 -0.1784 0.6038 0.3993 0.095 Uiso calc R 1 . .
C C5 0.0106(5) 0.6520(3) 0.4431(3) 0.0696(13) Uani d . 1 . .
H H5 -0.0175 0.7005 0.4660 0.084 Uiso calc R 1 . .
C C6 0.1501(4) 0.6374(3) 0.4484(3) 0.0545(10) Uani d . 1 . .
C C7 0.2570(5) 0.6974(3) 0.4934(4) 0.0745(14) Uani d . 1 . .
H H7A 0.3387 0.6698 0.5282 0.112 Uiso calc R 1 . .
H H7B 0.2222 0.7308 0.5386 0.112 Uiso calc R 1 . .
H H7C 0.2793 0.7304 0.4426 0.112 Uiso calc R 1 . .
N N2 0.2776(3) 0.43728(19) 0.3191(2) 0.0454(7) Uani d . 1 . .
C C10 0.3633(4) 0.3646(2) 0.3419(3) 0.0506(10) Uani d . 1 . .
H H10A 0.3885 0.3586 0.4130 0.061 Uiso calc R 1 . .
H H10B 0.4482 0.3737 0.3201 0.061 Uiso calc R 1 . .
C C11 0.3015(5) 0.2847(2) 0.2978(4) 0.0718(13) Uani d . 1 . .
H H11A 0.2089 0.2785 0.3084 0.086 Uiso calc R 1 . .
H H11B 0.2956 0.2843 0.2273 0.086 Uiso calc R 1 . .
C C12 0.3919(5) 0.2159(2) 0.3461(3) 0.0601(11) Uani d . 1 . .
C C13 0.3714(5) 0.1804(3) 0.4311(4) 0.0728(13) Uani d . 1 . .
H H13 0.2979 0.1975 0.4572 0.087 Uiso calc R 1 . .
C C14 0.4560(6) 0.1210(3) 0.4778(4) 0.0835(16) Uani d . 1 . .
H H14 0.4405 0.0985 0.5355 0.100 Uiso calc R 1 . .
C C15 0.5634(6) 0.0942(3) 0.4404(5) 0.0856(16) Uani d . 1 . .
H H15 0.6208 0.0532 0.4721 0.103 Uiso calc R 1 . .
C C16 0.5859(5) 0.1279(3) 0.3563(4) 0.0802(15) Uani d . 1 . .
H H16 0.6585 0.1094 0.3301 0.096 Uiso calc R 1 . .
C C17 0.5019(5) 0.1893(3) 0.3097(4) 0.0722(13) Uani d . 1 . .
H H17 0.5197 0.2129 0.2533 0.087 Uiso calc R 1 . .
N N3 0.4102(3) 0.57877(18) 0.2840(2) 0.0422(7) Uani d . 1 . .
C C20 0.2592(5) 0.4663(3) 0.2188(3) 0.0606(12) Uani d . 1 . .
H H20A 0.1659 0.4873 0.1970 0.073 Uiso calc R 1 . .
H H20B 0.2683 0.4211 0.1765 0.073 Uiso calc R 1 . .
C C21 0.3596(4) 0.5307(2) 0.2060(3) 0.0470(9) Uani d . 1 . .
C C22 0.3941(5) 0.5427(3) 0.1169(3) 0.0594(11) Uani d . 1 . .
H H22 0.3586 0.5088 0.0640 0.071 Uiso calc R 1 . .
C C23 0.4802(5) 0.6044(3) 0.1063(3) 0.0721(13) Uani d . 1 . .
H H23 0.5049 0.6125 0.0465 0.087 Uiso calc R 1 . .
C C24 0.5302(5) 0.6544(3) 0.1847(3) 0.0647(12) Uani d . 1 . .
H H24 0.5882 0.6972 0.1782 0.078 Uiso calc R 1 . .
C C25 0.4941(4) 0.6411(2) 0.2738(3) 0.0480(9) Uani d . 1 . .
C C26 0.5456(4) 0.6942(2) 0.3600(3) 0.0602(11) Uani d . 1 . .
H H26A 0.4772 0.7345 0.3632 0.090 Uiso calc R 1 . .
H H26B 0.6296 0.7201 0.3534 0.090 Uiso calc R 1 . .
H H26C 0.5633 0.6626 0.4193 0.090 Uiso calc R 1 . .
Cl Cl1 0.31371(15) 0.61419(8) 0.80233(9) 0.0761(4) Uani d D 1 . .
O O2 0.3428(4) 0.5652(3) 0.7274(3) 0.1062(13) Uani d . 1 A .
O O3A 0.1872(11) 0.6523(8) 0.754(2) 0.148(9) Uani d PD 0.45 A 1
O O4A 0.4110(16) 0.6693(10) 0.8592(17) 0.178(10) Uani d PD 0.45 A 1
O O5A 0.2839(15) 0.5531(7) 0.8670(11) 0.087(4) Uani d PD 0.45 A 1
O O3B 0.2421(15) 0.6843(6) 0.7572(17) 0.151(6) Uani d PD 0.55 A 2
O O4B 0.4497(4) 0.6397(7) 0.8511(10) 0.085(3) Uani d PD 0.55 A 2
O O5B 0.2323(17) 0.5784(9) 0.8635(14) 0.153(6) Uani d PD 0.55 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Cu1 O1 . 3_666 77.45(11) yes
O1 Cu1 N3 . . 167.88(11) yes
O1 Cu1 N3 3_666 . 90.44(11) yes
O1 Cu1 N1 . . 91.69(11) ?
O1 Cu1 N1 3_666 . 167.82(11) yes
N3 Cu1 N1 . . 100.31(12) ?
O1 Cu1 N2 . . 103.52(11) ?
O1 Cu1 N2 3_666 . 107.74(11) yes
N3 Cu1 N2 . . 80.51(12) yes
N1 Cu1 N2 . . 79.92(12) yes
Cu1 O1 Cu1 . 3_666 102.55(11) yes
Cu1 O1 H1 . . 133 ?
Cu1 O1 H1 3_666 . 115.10(19) ?
C2 N1 C6 . . 119.0(3) ?
C2 N1 Cu1 . . 115.2(3) ?
C6 N1 Cu1 . . 125.7(3) ?
N2 C1 C2 . . 112.7(3) ?
N2 C1 H1A . . 109.1 ?
C2 C1 H1A . . 109.1 ?
N2 C1 H1B . . 109.1 ?
C2 C1 H1B . . 109.1 ?
H1A C1 H1B . . 107.8 ?
N1 C2 C3 . . 122.1(4) ?
N1 C2 C1 . . 117.4(3) ?
C3 C2 C1 . . 120.4(4) ?
C4 C3 C2 . . 119.3(5) ?
C4 C3 H3 . . 120.4 ?
C2 C3 H3 . . 120.4 ?
C5 C4 C3 . . 119.6(4) ?
C5 C4 H4 . . 120.2 ?
C3 C4 H4 . . 120.2 ?
C4 C5 C6 . . 119.3(5) ?
C4 C5 H5 . . 120.3 ?
C6 C5 H5 . . 120.3 ?
N1 C6 C5 . . 120.6(4) ?
N1 C6 C7 . . 118.5(4) ?
C5 C6 C7 . . 120.8(4) ?
C6 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C6 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C20 N2 C1 . . 113.0(3) ?
C20 N2 C10 . . 114.8(3) ?
C1 N2 C10 . . 112.5(3) ?
C20 N2 Cu1 . . 106.3(2) ?
C1 N2 Cu1 . . 102.8(2) ?
C10 N2 Cu1 . . 106.2(2) ?
N2 C10 C11 . . 117.7(3) ?
N2 C10 H10A . . 107.9 ?
C11 C10 H10A . . 107.9 ?
N2 C10 H10B . . 107.9 ?
C11 C10 H10B . . 107.9 ?
H10A C10 H10B . . 107.2 ?
C12 C11 C10 . . 109.4(4) ?
C12 C11 H11A . . 109.8 ?
C10 C11 H11A . . 109.8 ?
C12 C11 H11B . . 109.8 ?
C10 C11 H11B . . 109.8 ?
H11A C11 H11B . . 108.2 ?
C17 C12 C13 . . 117.7(5) ?
C17 C12 C11 . . 121.2(5) ?
C13 C12 C11 . . 121.1(5) ?
C14 C13 C12 . . 121.6(5) ?
C14 C13 H13 . . 119.2 ?
C12 C13 H13 . . 119.2 ?
C13 C14 C15 . . 120.3(5) ?
C13 C14 H14 . . 119.9 ?
C15 C14 H14 . . 119.9 ?
C16 C15 C14 . . 119.5(5) ?
C16 C15 H15 . . 120.3 ?
C14 C15 H15 . . 120.3 ?
C15 C16 C17 . . 120.4(5) ?
C15 C16 H16 . . 119.8 ?
C17 C16 H16 . . 119.8 ?
C12 C17 C16 . . 120.5(5) ?
C12 C17 H17 . . 119.8 ?
C16 C17 H17 . . 119.8 ?
C21 N3 C25 . . 119.3(3) ?
C21 N3 Cu1 . . 115.8(2) ?
C25 N3 Cu1 . . 123.3(2) ?
N2 C20 C21 . . 114.2(3) ?
N2 C20 H20A . . 108.7 ?
C21 C20 H20A . . 108.7 ?
N2 C20 H20B . . 108.7 ?
C21 C20 H20B . . 108.7 ?
H20A C20 H20B . . 107.6 ?
N3 C21 C22 . . 121.2(4) ?
N3 C21 C20 . . 117.4(3) ?
C22 C21 C20 . . 121.3(4) ?
C23 C22 C21 . . 119.9(4) ?
C23 C22 H22 . . 120.0 ?
C21 C22 H22 . . 120.0 ?
C22 C23 C24 . . 119.3(4) ?
C22 C23 H23 . . 120.4 ?
C24 C23 H23 . . 120.4 ?
C23 C24 C25 . . 119.7(4) ?
C23 C24 H24 . . 120.1 ?
C25 C24 H24 . . 120.1 ?
N3 C25 C24 . . 120.5(4) ?
N3 C25 C26 . . 118.3(3) ?
C24 C25 C26 . . 121.2(4) ?
C25 C26 H26A . . 109.5 ?
C25 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C25 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
O2 Cl1 O5B . . 116.3(8) ?
O2 Cl1 O3B . . 108.0(10) ?
O5B Cl1 O3B . . 107.9(10) ?
O2 Cl1 O4A . . 123.6(10) ?
O2 Cl1 O4B . . 101.1(5) ?
O5B Cl1 O4B . . 116.1(11) ?
O3B Cl1 O4B . . 106.8(8) ?
O2 Cl1 O5A . . 99.6(7) ?
O4A Cl1 O5A . . 108.3(13) ?
O2 Cl1 O3A . . 102.3(12) ?
O4A Cl1 O3A . . 112.8(11) ?
O5A Cl1 O3A . . 108.9(12) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O1 . 1.931(2) yes
Cu1 O1 3_666 1.935(2) yes
Cu1 N3 . 2.040(3) yes
Cu1 N1 . 2.039(3) yes
Cu1 N2 . 2.263(3) yes
Cu1 Cu1 3_666 3.0161(8) yes
O1 Cu1 3_666 1.935(2) no
O1 H1 . 0.88 ?
N1 C2 . 1.340(5) ?
N1 C6 . 1.349(5) ?
C1 N2 . 1.453(5) ?
C1 C2 . 1.510(6) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 C3 . 1.368(6) ?
C3 C4 . 1.365(7) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.365(7) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.390(6) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.484(6) ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
N2 C20 . 1.449(5) ?
N2 C10 . 1.467(5) ?
C10 C11 . 1.528(5) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.510(6) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C17 . 1.377(6) ?
C12 C13 . 1.378(6) ?
C13 C14 . 1.359(7) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.363(7) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.361(7) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.380(7) ?
C16 H16 . 0.9300 ?
C17 H17 . 0.9300 ?
N3 C21 . 1.348(5) ?
N3 C25 . 1.354(5) ?
C20 C21 . 1.498(6) ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
C21 C22 . 1.374(6) ?
C22 C23 . 1.362(6) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.370(6) ?
C23 H23 . 0.9300 ?
C24 C25 . 1.385(5) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.483(5) ?
C26 H26A . 0.9600 ?
C26 H26B . 0.9600 ?
C26 H26C . 0.9600 ?
Cl1 O2 . 1.403(4) ?
Cl1 O5B . 1.4293(11) ?
Cl1 O3B . 1.4295(10) ?
Cl1 O4A . 1.4295(11) ?
Cl1 O4B . 1.4294(11) ?
Cl1 O5A . 1.4294(10) ?
Cl1 O3A . 1.4297(11) ?
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
O1 H1 O2 0.88 2.15 2.999(4) 161
