#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/49/2014966.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_2014966
loop_
_publ_author_name
'Ramos Silva, M.'
'Matos Beja, A.'
'Paixão, J. A.'
'Martin-Gil, J.'
_publ_section_title
Di-μ-chloro-1:2κ²Cl;3:4κ²Cl-hexachloro-1κ³Cl,4κ³Cl-tetra-μ-dimethylglycine-2:3κ⁸O:O'-tetracopper(II)
_journal_coeditor_code           BG1009
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m380
_journal_page_last               m382
_journal_paper_doi               10.1107/S0108270105021591
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          '[Cu4 Cl8 (C4 H9 N O2)4]'
_chemical_formula_moiety         'C16 H36 Cl8 Cu4 N4 O8'
_chemical_formula_sum            'C16 H36 Cl8 Cu4 N4 O8'
_chemical_formula_weight         950.25
_chemical_name_systematic
;
Octachloro-1κ⁴Cl,4κ⁴Cl-tetra-μ-dimethylglycine-2:3κ⁸O:O'-
tetracopper(II)]
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.20(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.7590(10)
_cell_length_b                   12.8610(10)
_cell_length_c                   14.0600(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15.93
_cell_measurement_theta_min      9.90
_cell_volume                     1742.0(3)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'PLATON (Spek, 2003)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'profile data from ω/2θ'
_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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3266
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         3.17
_diffrn_standards_decay_%        4.1
_diffrn_standards_interval_time  180
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.064
_exptl_absorpt_correction_T_max  0.303
_exptl_absorpt_correction_T_min  0.202
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.430
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3075
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0235
_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)+(0.0325P)²+1.4695P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0581
_refine_ls_wR_factor_ref         0.0635
_reflns_number_gt                2625
_reflns_number_total             3075
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bg1009.cif
_cod_data_source_block           I
_cod_original_cell_volume        1741.8(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2014966
_cod_database_fobs_code          2014966
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
Cu1 0.59767(3) -0.05778(2) 0.05727(2) 0.02322(9) Uani d . 1 . . Cu
Cu2 0.80484(3) 0.03701(2) 0.26202(2) 0.03025(10) Uani d . 1 . . Cu
Cl1 0.76619(7) -0.12398(5) 0.19292(5) 0.03222(15) Uani d . 1 . . Cl
Cl2 0.72292(8) 0.00060(6) 0.39923(5) 0.04465(19) Uani d . 1 . . Cl
Cl3 0.73336(9) 0.20340(6) 0.24919(5) 0.0481(2) Uani d . 1 . . Cl
Cl4 1.01405(8) 0.06124(7) 0.21906(7) 0.0547(2) Uani d . 1 . . Cl
O1 0.71701(18) 0.06279(13) 0.03822(14) 0.0305(4) Uani d . 1 . . O
O2 0.55297(18) 0.16049(14) -0.04852(14) 0.0351(4) Uani d . 1 . . O
O3 0.50695(19) 0.02369(15) 0.14862(13) 0.0340(4) Uani d . 1 . . O
O4 0.34662(19) 0.12127(14) 0.05746(13) 0.0340(4) Uani d . 1 . . O
N1 0.9150(2) 0.2101(2) 0.03939(18) 0.0368(6) Uani d . 1 . . N
H1 0.922(3) 0.167(3) 0.083(3) 0.044 Uiso d . 1 . . H
N2 0.4146(2) 0.07026(17) 0.31278(16) 0.0302(5) Uani d . 1 . . N
H2 0.509(3) 0.065(2) 0.320(2) 0.036 Uiso d . 1 . . H
C1 0.6723(3) 0.14454(19) -0.00322(18) 0.0256(5) Uani d . 1 . . C
C2 0.7680(3) 0.2372(2) 0.0039(2) 0.0311(6) Uani d . 1 . . C
H2A 0.7616 0.2692 -0.0591 0.037 Uiso calc R 1 . . H
H2B 0.7375 0.2880 0.0471 0.037 Uiso calc R 1 . . H
C3 0.9954(4) 0.3040(3) 0.0776(3) 0.0716(12) Uani d . 1 . . C
H3A 1.0905 0.2850 0.0991 0.107 Uiso calc R 1 . . H
H3B 0.9565 0.3322 0.1306 0.107 Uiso calc R 1 . . H
H3C 0.9911 0.3553 0.0276 0.107 Uiso calc R 1 . . H
C4 0.9797(4) 0.1568(4) -0.0356(3) 0.0670(11) Uani d . 1 . . C
H4A 1.0726 0.1363 -0.0090 0.101 Uiso calc R 1 . . H
H4B 0.9823 0.2032 -0.0888 0.101 Uiso calc R 1 . . H
H4C 0.9263 0.0963 -0.0576 0.101 Uiso calc R 1 . . H
C5 0.4099(3) 0.0885(2) 0.13612(19) 0.0272(5) Uani d . 1 . . C
C6 0.3643(3) 0.1331(2) 0.22518(19) 0.0293(6) Uani d . 1 . . C
H6A 0.3994 0.2035 0.2349 0.035 Uiso calc R 1 . . H
H6B 0.2638 0.1362 0.2157 0.035 Uiso calc R 1 . . H
C7 0.3818(4) 0.1243(3) 0.4001(2) 0.0500(8) Uani d . 1 . . C
H7A 0.4158 0.0838 0.4563 0.075 Uiso calc R 1 . . H
H7B 0.2831 0.1324 0.3948 0.075 Uiso calc R 1 . . H
H7C 0.4253 0.1915 0.4054 0.075 Uiso calc R 1 . . H
C8 0.3573(4) -0.0379(2) 0.3081(3) 0.0484(8) Uani d . 1 . . C
H8A 0.3968 -0.0754 0.3650 0.073 Uiso calc R 1 . . H
H8B 0.3801 -0.0725 0.2522 0.073 Uiso calc R 1 . . H
H8C 0.2583 -0.0351 0.3041 0.073 Uiso calc R 1 . . H
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'
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'
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'
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
O4 Cu1 O2 3_655 3_655 88.37(9) ?
O4 Cu1 O3 3_655 . 165.63(8) ?
O2 Cu1 O3 3_655 . 89.35(8) ?
O4 Cu1 O1 3_655 . 88.19(8) ?
O2 Cu1 O1 3_655 . 165.15(8) ?
O3 Cu1 O1 . . 90.40(8) ?
O4 Cu1 Cl1 3_655 . 104.74(6) ?
O2 Cu1 Cl1 3_655 . 102.49(6) ?
O3 Cu1 Cl1 . . 89.61(6) ?
O1 Cu1 Cl1 . . 92.35(6) ?
O4 Cu1 Cu1 3_655 3_655 90.04(6) ?
O2 Cu1 Cu1 3_655 3_655 83.35(6) ?
O3 Cu1 Cu1 . 3_655 75.60(6) ?
O1 Cu1 Cu1 . 3_655 82.21(5) ?
Cl1 Cu1 Cu1 . 3_655 164.13(2) yes
Cl4 Cu2 Cl3 . . 97.48(4) ?
Cl4 Cu2 Cl2 . . 136.30(4) yes
Cl3 Cu2 Cl2 . . 96.81(3) ?
Cl4 Cu2 Cl1 . . 96.12(3) ?
Cl3 Cu2 Cl1 . . 142.88(3) ?
Cl2 Cu2 Cl1 . . 96.80(3) ?
Cu2 Cl1 Cu1 . . 93.45(3) yes
C1 O1 Cu1 . . 123.61(16) ?
C1 O2 Cu1 . 3_655 123.19(17) ?
C5 O3 Cu1 . . 132.04(18) ?
C5 O4 Cu1 . 3_655 115.13(16) ?
C4 N1 C2 . . 111.7(2) ?
C4 N1 C3 . . 111.8(3) ?
C2 N1 C3 . . 110.8(3) ?
C4 N1 H1 . . 103(2) ?
C2 N1 H1 . . 112(2) ?
C3 N1 H1 . . 108(2) ?
C7 N2 C6 . . 110.0(2) ?
C7 N2 C8 . . 110.0(2) ?
C6 N2 C8 . . 113.4(2) ?
C7 N2 H2 . . 107(2) ?
C6 N2 H2 . . 109.5(19) ?
C8 N2 H2 . . 107.0(19) ?
O1 C1 O2 . . 127.1(2) ?
O1 C1 C2 . . 118.0(2) ?
O2 C1 C2 . . 114.9(2) ?
N1 C2 C1 . . 113.1(2) ?
N1 C2 H2A . . 109.0 ?
C1 C2 H2A . . 109.0 ?
N1 C2 H2B . . 109.0 ?
C1 C2 H2B . . 109.0 ?
H2A C2 H2B . . 107.8 ?
N1 C3 H3A . . 109.5 ?
N1 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
N1 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
N1 C4 H4A . . 109.5 ?
N1 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
N1 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
O4 C5 O3 . . 127.1(2) ?
O4 C5 C6 . . 115.9(2) ?
O3 C5 C6 . . 117.0(2) ?
N2 C6 C5 . . 112.2(2) ?
N2 C6 H6A . . 109.2 ?
C5 C6 H6A . . 109.2 ?
N2 C6 H6B . . 109.2 ?
C5 C6 H6B . . 109.2 ?
H6A C6 H6B . . 107.9 ?
N2 C7 H7A . . 109.5 ?
N2 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
N2 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
N2 C8 H8A . . 109.5 ?
N2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
N2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
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 O4 3_655 1.9608(19) yes
Cu1 O2 3_655 1.9656(18) yes
Cu1 O3 . 1.9735(18) yes
Cu1 O1 . 1.9830(17) yes
Cu1 Cl1 . 2.4625(9) yes
Cu1 Cu1 3_655 2.7303(8) yes
Cu2 Cl4 . 2.2416(9) yes
Cu2 Cl3 . 2.2490(8) yes
Cu2 Cl2 . 2.2523(9) yes
Cu2 Cl1 . 2.2925(7) yes
O1 C1 . 1.246(3) ?
O2 C1 . 1.252(3) ?
O2 Cu1 3_655 1.9656(18) ?
O3 C5 . 1.253(3) ?
O4 C5 . 1.250(3) ?
O4 Cu1 3_655 1.9608(19) ?
N1 C4 . 1.482(5) ?
N1 C2 . 1.482(4) ?
N1 C3 . 1.493(4) ?
N1 H1 . 0.82(3) ?
N2 C7 . 1.489(4) ?
N2 C6 . 1.489(3) ?
N2 C8 . 1.496(4) ?
N2 H2 . 0.91(3) ?
C1 C2 . 1.508(4) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 H3A . 0.9600 ?
C3 H3B . 0.9600 ?
C3 H3C . 0.9600 ?
C4 H4A . 0.9600 ?
C4 H4B . 0.9600 ?
C4 H4C . 0.9600 ?
C5 C6 . 1.507(4) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C6 H6B Cl4 1_455 0.97 2.63 3.529(3) 155
C7 H7C O2 4_566 0.96 2.31 3.254(4) 167
C2 H2A Cl3 4_565 0.97 2.69 3.625(3) 162
C8 H8C Cl4 1_455 0.96 2.78 3.616(4) 146
N1 H1 Cl4 . 0.82(3) 2.40(4) 3.194(3) 162(3)
N2 H2 Cl2 . 0.91(3) 2.35(3) 3.188(3) 153(3)
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_site_symmetry_1
_geom_torsion
_geom_torsion_publ_flag
Cl4 Cu2 Cl1 Cu1 . -105.25(3) yes
Cl3 Cu2 Cl1 Cu1 . 5.77(6) yes
Cl2 Cu2 Cl1 Cu1 . 116.58(3) yes
O4 Cu1 Cl1 Cu2 3_655 133.21(6) ?
O2 Cu1 Cl1 Cu2 3_655 -135.17(7) ?
O3 Cu1 Cl1 Cu2 . -45.92(6) ?
O1 Cu1 Cl1 Cu2 . 44.46(6) ?
Cu1 Cu1 Cl1 Cu2 3_655 -24.95(10) yes
O4 Cu1 O1 C1 3_655 97.4(2) ?
O2 Cu1 O1 C1 3_655 20.7(4) ?
O3 Cu1 O1 C1 . -68.3(2) ?
Cl1 Cu1 O1 C1 . -157.96(19) ?
Cu1 Cu1 O1 C1 3_655 7.06(19) ?
O4 Cu1 O3 C5 3_655 -1.7(5) ?
O2 Cu1 O3 C5 3_655 -82.6(2) ?
O1 Cu1 O3 C5 . 82.5(2) ?
Cl1 Cu1 O3 C5 . 174.9(2) ?
Cu1 Cu1 O3 C5 3_655 0.7(2) ?
Cu1 O1 C1 O2 . -8.9(4) ?
Cu1 O1 C1 C2 . 168.39(18) ?
Cu1 O2 C1 O1 3_655 3.9(4) ?
Cu1 O2 C1 C2 3_655 -173.54(17) ?
C4 N1 C2 C1 . 74.5(3) ?
C3 N1 C2 C1 . -160.2(3) ?
O1 C1 C2 N1 . 14.5(3) ?
O2 C1 C2 N1 . -167.9(2) ?
Cu1 O4 C5 O3 3_655 3.1(4) ?
Cu1 O4 C5 C6 3_655 -177.53(17) ?
Cu1 O3 C5 O4 . -2.6(4) ?
Cu1 O3 C5 C6 . 177.95(17) ?
C7 N2 C6 C5 . 173.1(2) ?
C8 N2 C6 C5 . -63.2(3) ?
O4 C5 C6 N2 . 163.9(2) ?
O3 C5 C6 N2 . -16.6(3) ?
