#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/20/2212036.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_2212036
loop_
_publ_author_name
'Kirillov, Alexander M.'
'Haukka, Matti'
'Kopylovich, Maximilian N.'
'Pombeiro, Armando J. L.'
_publ_section_title
;Bis{μ-2-[bis(2-hydroxyethyl)amino]ethanolato}bis(4-methylbenzoato)dicopper(II)
 dihydrate
;
_journal_coeditor_code           BI2138
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m526
_journal_page_last               m528
_journal_paper_doi               10.1107/S1600536807001687
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Cu2 (C8 H7 O2)2 (C6 H14 N O3)2], 2H2 O'
_chemical_formula_moiety         'C28 H42 Cu2 N2 O10, 2(H2 O)'
_chemical_formula_sum            'C28 H46 Cu2 N2 O12'
_chemical_formula_weight         729.75
_chemical_name_systematic
;Bis{μ-2-[bis(2-hydroxyethyl)amino]ethanolato}bis(4-methylbenzoato)dicopper(II)
dihydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                75.422(3)
_cell_angle_beta                 87.976(4)
_cell_angle_gamma                70.805(4)
_cell_formula_units_Z            1
_cell_length_a                   7.5137(5)
_cell_length_b                   7.9384(5)
_cell_length_c                   14.3761(10)
_cell_measurement_reflns_used    19611
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     782.69(9)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        DENZO/SCALEPACK
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_sigmaI/netI    0.0552
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12377
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.81
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.423
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.794
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(XPREP; Bruker, 2005)'
_exptl_crystal_colour            'pale blue'
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             382
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.661
_refine_diff_density_min         -0.418
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3429
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0307P)²+0.6222P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0797
_refine_ls_wR_factor_ref         0.0860
_reflns_number_gt                2743
_reflns_number_total             3429
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi2138.cif
_cod_data_source_block           I
_cod_database_code               2212036
_cod_database_fobs_code          2212036
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Cu Cu1 0.50352(4) 0.05251(4) 0.89570(2) 0.01727(11) Uani d . 1
O O1 0.2281(3) -0.0070(2) 0.83087(13) 0.0212(4) Uani d . 1
H H1O 0.3040 -0.0583 0.7878 0.032 Uiso d R 1
O O2 0.7261(3) 0.2210(2) 0.89230(13) 0.0232(4) Uani d . 1
H H2O 0.8020 0.2238 0.9353 0.035 Uiso d R 1
O O3 0.6471(2) -0.1441(2) 1.00309(12) 0.0165(4) Uani d . 1
O O4 0.6550(2) -0.0472(2) 0.79689(13) 0.0199(4) Uani d . 1
O O5 0.4815(3) -0.1644(3) 0.72423(14) 0.0251(4) Uani d . 1
N N1 0.3640(3) 0.3093(3) 0.80933(15) 0.0173(5) Uani d . 1
C C1 0.1231(4) 0.1726(4) 0.7756(2) 0.0236(6) Uani d . 1
H H1A 0.0294 0.2355 0.8166 0.028 Uiso calc R 1
H H1B 0.0530 0.1613 0.7218 0.028 Uiso calc R 1
C C2 0.2447(4) 0.2914(3) 0.73484(19) 0.0200(6) Uani d . 1
H H2A 0.3272 0.2369 0.6873 0.024 Uiso calc R 1
H H2B 0.1617 0.4159 0.7005 0.024 Uiso calc R 1
C C3 0.6440(4) 0.4012(3) 0.83068(19) 0.0220(6) Uani d . 1
H H3A 0.7433 0.4441 0.7956 0.026 Uiso calc R 1
H H3B 0.5783 0.4890 0.8690 0.026 Uiso calc R 1
C C4 0.5059(4) 0.3909(4) 0.76060(19) 0.0206(6) Uani d . 1
H H4A 0.4394 0.5166 0.7206 0.025 Uiso calc R 1
H H4B 0.5761 0.3156 0.7173 0.025 Uiso calc R 1
C C5 0.6805(4) -0.3363(3) 1.02155(19) 0.0196(6) Uani d . 1
H H5A 0.7756 -0.3903 0.9784 0.024 Uiso calc R 1
H H5B 0.5624 -0.3595 1.0104 0.024 Uiso calc R 1
C C6 0.2474(4) 0.4224(3) 0.87331(19) 0.0205(6) Uani d . 1
H H6A 0.1140 0.4301 0.8668 0.025 Uiso calc R 1
H H6B 0.2532 0.5492 0.8530 0.025 Uiso calc R 1
C C7 0.6271(4) -0.1276(3) 0.73515(19) 0.0184(6) Uani d . 1
C C8 0.7862(4) -0.1770(3) 0.66949(19) 0.0189(6) Uani d . 1
C C9 0.9583(4) -0.1558(3) 0.68504(19) 0.0207(6) Uani d . 1
H H9 0.9782 -0.1154 0.7394 0.025 Uiso calc R 1
C C10 1.1014(4) -0.1931(3) 0.6218(2) 0.0213(6) Uani d . 1
H H10 1.2175 -0.1760 0.6329 0.026 Uiso calc R 1
C C11 1.0767(4) -0.2552(4) 0.54250(19) 0.0216(6) Uani d . 1
C C12 1.2348(4) -0.2996(4) 0.4757(2) 0.0291(7) Uani d . 1
H H12A 1.2856 -0.1975 0.4576 0.044 Uiso calc R 1
H H12B 1.1866 -0.3176 0.4177 0.044 Uiso calc R 1
H H12C 1.3350 -0.4127 0.5083 0.044 Uiso calc R 1
C C13 0.9048(4) -0.2766(4) 0.5272(2) 0.0249(6) Uani d . 1
H H13 0.8854 -0.3179 0.4731 0.030 Uiso calc R 1
C C14 0.7606(4) -0.2382(4) 0.5901(2) 0.0247(6) Uani d . 1
H H14 0.6440 -0.2539 0.5787 0.030 Uiso calc R 1
O O6 0.0414(3) -0.2060(2) 0.96641(13) 0.0240(4) Uani d . 1
H H6O 0.0767 -0.1397 0.9213 0.036 Uiso d R 1
H H6P -0.0846 -0.1521 0.9607 0.036 Uiso d R 1
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 Cu1 O4 . . 95.09(7) yes
O3 Cu1 O3 . 2_657 83.42(7) yes
O4 Cu1 O3 . 2_657 178.13(7) ?
O3 Cu1 N1 . . 161.95(8) yes
O4 Cu1 N1 . . 96.98(8) yes
O3 Cu1 N1 2_657 . 84.73(8) ?
O3 Cu1 O2 . . 91.36(7) yes
O4 Cu1 O2 . . 84.90(7) yes
O3 Cu1 O2 2_657 . 96.25(7) ?
N1 Cu1 O2 . . 76.44(7) yes
O3 Cu1 O1 . . 114.12(6) yes
O4 Cu1 O1 . . 88.55(7) yes
O3 Cu1 O1 2_657 . 91.03(7) ?
N1 Cu1 O1 . . 79.62(7) yes
O2 Cu1 O1 . . 154.18(6) yes
O3 Cu1 Cu1 . 2_657 41.78(5) ?
O4 Cu1 Cu1 . 2_657 136.86(6) ?
O3 Cu1 Cu1 2_657 2_657 41.64(5) ?
N1 Cu1 Cu1 . 2_657 125.05(6) ?
O2 Cu1 Cu1 . 2_657 95.10(5) ?
O1 Cu1 Cu1 . 2_657 106.58(4) ?
C1 O1 Cu1 . . 101.16(14) ?
C1 O1 H1O . . 103.7 ?
Cu1 O1 H1O . . 89.3 ?
C3 O2 Cu1 . . 107.89(15) ?
C3 O2 H2O . . 109.8 ?
Cu1 O2 H2O . . 133.5 ?
C5 O3 Cu1 . . 128.55(15) ?
C5 O3 Cu1 . 2_657 108.71(14) ?
Cu1 O3 Cu1 . 2_657 96.58(7) yes
C7 O4 Cu1 . . 133.91(17) ?
C2 N1 C4 . . 108.6(2) ?
C2 N1 C6 . . 111.6(2) ?
C4 N1 C6 . . 111.5(2) ?
C2 N1 Cu1 . . 109.22(15) ?
C4 N1 Cu1 . . 108.73(15) ?
C6 N1 Cu1 . . 107.07(15) ?
O1 C1 C2 . . 113.6(2) ?
O1 C1 H1A . . 108.9 ?
C2 C1 H1A . . 108.9 ?
O1 C1 H1B . . 108.9 ?
C2 C1 H1B . . 108.9 ?
H1A C1 H1B . . 107.7 ?
N1 C2 C1 . . 113.3(2) ?
N1 C2 H2A . . 108.9 ?
C1 C2 H2A . . 108.9 ?
N1 C2 H2B . . 108.9 ?
C1 C2 H2B . . 108.9 ?
H2A C2 H2B . . 107.7 ?
O2 C3 C4 . . 107.7(2) ?
O2 C3 H3A . . 110.2 ?
C4 C3 H3A . . 110.2 ?
O2 C3 H3B . . 110.2 ?
C4 C3 H3B . . 110.2 ?
H3A C3 H3B . . 108.5 ?
N1 C4 C3 . . 112.7(2) ?
N1 C4 H4A . . 109.1 ?
C3 C4 H4A . . 109.1 ?
N1 C4 H4B . . 109.1 ?
C3 C4 H4B . . 109.1 ?
H4A C4 H4B . . 107.8 ?
O3 C5 C6 . 2_657 107.3(2) ?
O3 C5 H5A . . 110.3 ?
C6 C5 H5A 2_657 . 110.3 ?
O3 C5 H5B . . 110.3 ?
C6 C5 H5B 2_657 . 110.3 ?
H5A C5 H5B . . 108.5 ?
N1 C6 C5 . 2_657 110.7(2) ?
N1 C6 H6A . . 109.5 ?
C5 C6 H6A 2_657 . 109.5 ?
N1 C6 H6B . . 109.5 ?
C5 C6 H6B 2_657 . 109.5 ?
H6A C6 H6B . . 108.1 ?
O5 C7 O4 . . 125.9(2) ?
O5 C7 C8 . . 118.7(2) ?
O4 C7 C8 . . 115.4(2) ?
C14 C8 C9 . . 118.8(2) ?
C14 C8 C7 . . 120.4(2) ?
C9 C8 C7 . . 120.8(2) ?
C10 C9 C8 . . 120.6(3) ?
C10 C9 H9 . . 119.7 ?
C8 C9 H9 . . 119.7 ?
C9 C10 C11 . . 120.7(2) ?
C9 C10 H10 . . 119.6 ?
C11 C10 H10 . . 119.6 ?
C13 C11 C10 . . 118.5(2) ?
C13 C11 C12 . . 121.2(3) ?
C10 C11 C12 . . 120.3(2) ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C11 C13 C14 . . 120.9(3) ?
C11 C13 H13 . . 119.5 ?
C14 C13 H13 . . 119.5 ?
C8 C14 C13 . . 120.4(3) ?
C8 C14 H14 . . 119.8 ?
C13 C14 H14 . . 119.8 ?
H6O O6 H6P . . 102.5 ?
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 O1 . 2.5249(18) yes
Cu1 O2 . 2.4535(18) yes
Cu1 O3 . 1.9443(17) yes
Cu1 O3 2_657 1.9497(17) yes
Cu1 O4 . 1.9491(18) yes
Cu1 N1 . 2.051(2) yes
Cu1 Cu1 2_657 2.9070(7) ?
O1 C1 . 1.422(3) ?
O1 H1O . 0.908 ?
O2 C3 . 1.425(3) ?
O2 H2O . 0.865 ?
O3 C5 . 1.418(3) ?
O3 Cu1 2_657 1.9498(17) ?
O4 C7 . 1.275(3) ?
O5 C7 . 1.246(3) ?
N1 C2 . 1.483(3) ?
N1 C4 . 1.490(3) ?
N1 C6 . 1.504(3) ?
C1 C2 . 1.522(4) ?
C1 H1A . 0.990 ?
C1 H1B . 0.990 ?
C2 H2A . 0.990 ?
C2 H2B . 0.990 ?
C3 C4 . 1.507(4) ?
C3 H3A . 0.990 ?
C3 H3B . 0.990 ?
C4 H4A . 0.990 ?
C4 H4B . 0.990 ?
C5 C6 2_657 1.530(4) ?
C5 H5A . 0.990 ?
C5 H5B . 0.990 ?
C6 C5 2_657 1.530(4) ?
C6 H6A . 0.990 ?
C6 H6B . 0.990 ?
C7 C8 . 1.507(4) ?
C8 C14 . 1.390(4) ?
C8 C9 . 1.391(4) ?
C9 C10 . 1.388(4) ?
C9 H9 . 0.950 ?
C10 C11 . 1.392(4) ?
C10 H10 . 0.950 ?
C11 C13 . 1.388(4) ?
C11 C12 . 1.507(4) ?
C12 H12A . 0.980 ?
C12 H12B . 0.980 ?
C12 H12C . 0.980 ?
C13 C14 . 1.391(4) ?
C13 H13 . 0.950 ?
C14 H14 . 0.950 ?
O6 H6O . 0.822 ?
O6 H6P . 0.898 ?
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
_geom_hbond_publ_flag
O1 H1O O5 . 0.91 1.70 2.594(3) 168.4 yes
O2 H2O O6 2_657 0.87 1.82 2.680(3) 173.6 yes
O6 H6O O1 . 0.82 2.02 2.824(3) 165.1 yes
O6 H6P O3 1_455 0.90 2.07 2.891(2) 151.3 yes
