#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/46/2014607.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_2014607
loop_
_publ_author_name
'Rojas, Dario'
'García, Ana María'
'Manzur, Jorge'
'Vega, Andrés'
_publ_section_title
;Di-μ-hydroxo-bis{(acetonitrile)dibenzyl(6-methyl-2-pyridylmethyl)amine-κ²N,N]copper(II)}
 bis(perchlorate)
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m115
_journal_page_last               m116
_journal_paper_doi               10.1107/S010827010500034X
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac
'[Cu2 (O H)2 (C2 H3 N1)2 (C21 H22 N2)2] (Cl O4)2'
_chemical_formula_moiety         'C46 H52 Cu2 N6 O2 2+ , 2Cl O4 -'
_chemical_formula_sum            'C46 H52 Cl2 Cu2 N6 O10'
_chemical_formula_weight         1046.94
_chemical_name_systematic
;
Di-μ-hydroxo-bis{(acetonitrile)[N-benzyl-N-(6-methyl-2-
pyridylmethyl)benzylamine-κ²N',N'']copper(II)} diperchlorate
;
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.193(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.1453(10)
_cell_length_b                   20.0868(19)
_cell_length_c                   12.0925(12)
_cell_measurement_reflns_used    3378
_cell_measurement_temperature    571(2)
_cell_measurement_theta_max      46.691
_cell_measurement_theta_min      4.628
_cell_volume                     2378.2(4)
_computing_data_collection       'SMART-NT (Bruker, 2001)'
_computing_data_reduction        'SAINT-NT (Bruker, 1999)'
_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      571(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12077
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.02
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.070
_exptl_absorpt_correction_T_max  0.618
_exptl_absorpt_correction_T_min  0.572
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   '(SADABS in SAINT-NT; Bruker, 1999)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1084
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.45
_refine_diff_density_max         0.760
_refine_diff_density_min         -0.744
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4218
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0571
_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)+(0.1158P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1692
_refine_ls_wR_factor_ref         0.1826
_reflns_number_gt                3006
_reflns_number_total             4218
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            av1222.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (6 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Y' changed to 'y'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (6
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (13 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2014607
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_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
_atom_site_type_symbol
Cu 0.39369(5) -0.00309(2) 0.89022(4) 0.0369(2) Uani d . 1 . . Cu
O1 0.5473(3) 0.05049(14) 0.9675(2) 0.0431(7) Uani d . 1 . . O
H1 0.6163 0.0577 0.9285 0.10(2) Uiso d . 1 . . H
N1 0.2476(4) -0.06543(16) 0.7961(3) 0.0402(8) Uani d . 1 . . N
C1 0.3294(6) -0.1707(2) 0.8914(5) 0.0691(15) Uani d . 1 . . C
H1A 0.4164 -0.1487 0.9096 0.104 Uiso calc R 1 . . H
H1B 0.3387 -0.2145 0.8626 0.104 Uiso calc R 1 . . H
H1C 0.2973 -0.1740 0.9591 0.104 Uiso calc R 1 . . H
C2 0.2299(5) -0.1318(2) 0.8028(4) 0.0490(11) Uani d . 1 . . C
C3 0.1183(6) -0.1628(3) 0.7287(5) 0.0651(15) Uani d . 1 . . C
H3 0.1071 -0.2086 0.7333 0.078 Uiso calc R 1 . . H
C4 0.0259(6) -0.1268(3) 0.6500(5) 0.0709(16) Uani d . 1 . . C
H4 -0.0502 -0.1474 0.6026 0.085 Uiso calc R 1 . . H
C5 0.0461(5) -0.0597(3) 0.6412(4) 0.0596(14) Uani d . 1 . . C
H5 -0.0156 -0.0341 0.5874 0.072 Uiso calc R 1 . . H
C6 0.1585(4) -0.0310(2) 0.7130(4) 0.0430(11) Uani d . 1 . . C
C7 0.1885(4) 0.0415(2) 0.7032(4) 0.0437(11) Uani d . 1 . . C
H7A 0.1569 0.0550 0.6237 0.052 Uiso calc R 1 . . H
H7B 0.1387 0.0672 0.7469 0.052 Uiso calc R 1 . . H
N2 0.3366(3) 0.05635(16) 0.7457(3) 0.0383(8) Uani d . 1 . . N
C8 0.4144(5) 0.0414(2) 0.6595(4) 0.0508(12) Uani d . 1 . . C
H8A 0.5031 0.0629 0.6834 0.061 Uiso calc R 1 . . H
H8B 0.3661 0.0606 0.5865 0.061 Uiso calc R 1 . . H
C9 0.4352(5) -0.0315(3) 0.6428(4) 0.0531(12) Uani d . 1 . . C
C10 0.3506(6) -0.0668(3) 0.5540(5) 0.0709(16) Uani d . 1 . . C
H10 0.2838 -0.0451 0.4982 0.085 Uiso calc R 1 . . H
C11 0.3674(8) -0.1363(4) 0.5493(7) 0.096(2) Uani d . 1 . . C
H11 0.3098 -0.1606 0.4908 0.116 Uiso calc R 1 . . H
C12 0.4658(9) -0.1681(4) 0.6285(8) 0.098(2) Uani d . 1 . . C
H12 0.4736 -0.2142 0.6259 0.117 Uiso calc R 1 . . H
C13 0.5538(7) -0.1326(3) 0.7123(6) 0.0837(19) Uani d . 1 . . C
H13 0.6249 -0.1542 0.7642 0.100 Uiso calc R 1 . . H
C14 0.5378(6) -0.0651(3) 0.7204(5) 0.0640(14) Uani d . 1 . . C
H14 0.5971 -0.0416 0.7790 0.077 Uiso calc R 1 . . H
C15 0.3537(4) 0.12901(19) 0.7795(4) 0.0434(11) Uani d . 1 . . C
H15A 0.3144 0.1362 0.8435 0.052 Uiso calc R 1 . . H
H15B 0.4505 0.1387 0.8058 0.052 Uiso calc R 1 . . H
C16 0.2899(4) 0.1773(2) 0.6862(4) 0.0437(11) Uani d . 1 . . C
C17 0.1583(5) 0.2006(2) 0.6742(4) 0.0511(12) Uani d . 1 . . C
H17 0.1092 0.1866 0.7249 0.061 Uiso calc R 1 . . H
C18 0.0996(5) 0.2446(2) 0.5868(5) 0.0580(14) Uani d . 1 . . C
H18 0.0103 0.2589 0.5782 0.070 Uiso calc R 1 . . H
C19 0.1712(6) 0.2671(2) 0.5136(4) 0.0588(14) Uani d . 1 . . C
H19 0.1316 0.2971 0.4559 0.071 Uiso calc R 1 . . H
C20 0.3018(6) 0.2453(2) 0.5256(5) 0.0654(15) Uani d . 1 . . C
H20 0.3506 0.2601 0.4751 0.078 Uiso calc R 1 . . H
C21 0.3619(5) 0.2013(2) 0.6121(5) 0.0558(13) Uani d . 1 . . C
H21 0.4516 0.1877 0.6206 0.067 Uiso calc R 1 . . H
N3 0.2201(4) 0.0519(2) 0.9695(4) 0.0599(11) Uani d . 1 . . N
C22 0.1587(5) 0.0594(2) 1.0321(5) 0.0540(13) Uani d . 1 . . C
C23 0.0792(7) 0.0684(3) 1.1156(6) 0.0842(19) Uani d . 1 . . C
H23A 0.0011 0.0957 1.0830 0.126 Uiso calc R 1 . . H
H23B 0.1348 0.0896 1.1829 0.126 Uiso calc R 1 . . H
H23C 0.0495 0.0258 1.1359 0.126 Uiso calc R 1 . . H
ClA 0.81252(13) 0.12494(7) 0.80005(13) 0.0693(5) Uani d PD 0.60 A 1 Cl
O2A 0.7094(8) 0.1640(4) 0.7324(9) 0.116(4) Uiso d PD 0.60 A 1 O
O3A 0.9310(7) 0.1617(5) 0.8419(11) 0.143(4) Uiso d PD 0.60 A 1 O
O4A 0.8574(11) 0.0838(5) 0.7248(8) 0.147(4) Uiso d PD 0.60 A 1 O
O5A 0.7786(10) 0.0821(5) 0.8762(9) 0.114(3) Uiso d P 0.60 A 1 O
ClB 0.81252(13) 0.12494(7) 0.80005(13) 0.0693(5) Uani d PD 0.40 B 2 Cl
O2B 0.6926(11) 0.1652(8) 0.7825(17) 0.141(7) Uiso d PD 0.40 B 2 O
O3B 0.8673(19) 0.1548(9) 0.9098(8) 0.168(7) Uiso d PD 0.40 B 2 O
O4B 0.910(2) 0.1394(15) 0.737(2) 0.237(11) Uiso d PD 0.40 B 2 O
O5B 0.7293(16) 0.0725(8) 0.7984(15) 0.131(5) Uiso d P 0.40 B 2 O
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
_geom_angle_publ_flag
O1 Cu O1 3_657 79.61(13) y
O1 Cu N1 3_657 101.86(13) y
O1 Cu N1 . 172.23(14) y
O1 Cu N2 3_657 174.44(12) y
O1 Cu N2 . 95.69(12) y
N1 Cu N2 . 83.20(14) y
O1 Cu N3 3_657 87.74(14) y
O1 Cu N3 . 97.49(14) y
N1 Cu N3 . 90.21(14) y
N2 Cu N3 . 89.97(14) y
Cu O1 Cu 3_657 100.39(13) y
Cu O1 H1 3_657 115.0 y
Cu O1 H1 . 116.9 y
C2 N1 C6 . 118.4(4) ?
C2 C1 H1A . 109.5 ?
C2 C1 H1B . 109.5 ?
H1A C1 H1B . 109.5 ?
C2 C1 H1C . 109.5 ?
H1A C1 H1C . 109.5 ?
H1B C1 H1C . 109.5 ?
N1 C2 C3 . 120.1(5) ?
N1 C2 C1 . 119.1(4) ?
C3 C2 C1 . 120.8(4) ?
C4 C3 C2 . 120.6(5) ?
C4 C3 H3 . 119.7 ?
C2 C3 H3 . 119.7 ?
C3 C4 C5 . 119.2(5) ?
C3 C4 H4 . 120.4 ?
C5 C4 H4 . 120.4 ?
C6 C5 C4 . 118.8(5) ?
C6 C5 H5 . 120.6 ?
C4 C5 H5 . 120.6 ?
N1 C6 C5 . 122.8(4) ?
N1 C6 C7 . 116.4(3) ?
C5 C6 C7 . 120.8(4) ?
N2 C7 C6 . 112.1(3) ?
N2 C7 H7A . 109.2 ?
C6 C7 H7A . 109.2 ?
N2 C7 H7B . 109.2 ?
C6 C7 H7B . 109.2 ?
H7A C7 H7B . 107.9 ?
C7 N2 C8 . 112.9(3) ?
C7 N2 C15 . 108.7(3) ?
C8 N2 C15 . 109.7(3) ?
C7 N2 Cu . 102.1(2) ?
C8 N2 Cu . 113.1(3) ?
C15 N2 Cu . 110.0(2) ?
N2 C8 C9 . 114.0(4) ?
N2 C8 H8A . 108.7 ?
C9 C8 H8A . 108.7 ?
N2 C8 H8B . 108.7 ?
C9 C8 H8B . 108.7 ?
H8A C8 H8B . 107.6 ?
C14 C9 C10 . 118.7(5) ?
C14 C9 C8 . 119.5(4) ?
C10 C9 C8 . 121.7(5) ?
C9 C10 C11 . 118.9(6) ?
C9 C10 H10 . 120.6 ?
C11 C10 H10 . 120.6 ?
C12 C11 C10 . 121.0(6) ?
C12 C11 H11 . 119.5 ?
C10 C11 H11 . 119.5 ?
C11 C12 C13 . 119.9(6) ?
C11 C12 H12 . 120.1 ?
C13 C12 H12 . 120.1 ?
C12 C13 C14 . 120.2(6) ?
C12 C13 H13 . 119.9 ?
C14 C13 H13 . 119.9 ?
C13 C14 C9 . 121.1(6) ?
C13 C14 H14 . 119.4 ?
C9 C14 H14 . 119.4 ?
C16 C15 N2 . 115.1(3) ?
C16 C15 H15A . 108.5 ?
N2 C15 H15A . 108.5 ?
C16 C15 H15B . 108.5 ?
N2 C15 H15B . 108.5 ?
H15A C15 H15B . 107.5 ?
C21 C16 C17 . 118.2(4) ?
C21 C16 C15 . 121.0(4) ?
C17 C16 C15 . 120.7(4) ?
C16 C17 C18 . 120.3(5) ?
C16 C17 H17 . 119.8 ?
C18 C17 H17 . 119.8 ?
C19 C18 C17 . 120.7(5) ?
C19 C18 H18 . 119.6 ?
C17 C18 H18 . 119.6 ?
C18 C19 C20 . 119.5(5) ?
C18 C19 H19 . 120.2 ?
C20 C19 H19 . 120.2 ?
C19 C20 C21 . 120.5(5) ?
C19 C20 H20 . 119.7 ?
C21 C20 H20 . 119.7 ?
C20 C21 C16 . 120.6(5) ?
C20 C21 H21 . 119.7 ?
C16 C21 H21 . 119.7 ?
C22 N3 Cu . 155.2(4) y
N3 C22 C23 . 179.2(6) ?
C22 C23 H23A . 109.5 ?
C22 C23 H23B . 109.5 ?
H23A C23 H23B . 109.5 ?
C22 C23 H23C . 109.5 ?
H23A C23 H23C . 109.5 ?
H23B C23 H23C . 109.5 ?
O5A ClA O3A . 115.8(7) ?
O5A ClA O2A . 117.9(6) ?
O3A ClA O2A . 111.1(6) ?
O5A ClA O4A . 104.5(7) ?
O3A ClA O4A . 98.9(7) ?
O2A ClA O4A . 106.0(7) ?
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
Cu O1 3_657 1.920(3) y
Cu O1 . 1.923(3) y
Cu N1 . 2.044(3) y
Cu N2 . 2.070(3) y
Cu N3 . 2.476(5) y
Cu Cu 3_657 2.9522(9) y
O1 Cu 3_657 1.920(3) ?
O1 H1 . 0.952 ?
N1 C2 . 1.350(5) ?
N1 C6 . 1.352(5) ?
C1 C2 . 1.487(7) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C3 . 1.393(7) ?
C3 C4 . 1.356(8) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.373(7) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.366(6) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.500(6) ?
C7 N2 . 1.485(5) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
N2 C8 . 1.494(6) ?
N2 C15 . 1.513(5) ?
C8 C9 . 1.501(7) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C14 . 1.381(7) ?
C9 C10 . 1.382(7) ?
C10 C11 . 1.408(8) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.350(10) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.362(9) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.372(8) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 C16 . 1.500(6) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 C21 . 1.382(6) ?
C16 C17 . 1.386(6) ?
C17 C18 . 1.387(7) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.361(7) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.367(7) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.384(6) ?
C20 H20 . 0.9300 ?
C21 H21 . 0.9300 ?
N3 C22 . 1.109(6) ?
C22 C23 . 1.459(8) ?
C23 H23A . 0.9600 ?
C23 H23B . 0.9600 ?
C23 H23C . 0.9600 ?
ClA O5A . 1.369(10) ?
ClA O3A . 1.3890(10) ?
ClA O2A . 1.3900(7) ?
ClA O4A . 1.3911(10) ?
