#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/00/1500029.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_1500029
loop_
_publ_author_name
'Carmen R. Maldonado'
'Miguel Quirós'
'Juan M. Salas'
_publ_contact_author_address
;
     Departamento de Química Inorgánica
     Facultad de Ciencias
     Universidad de Granada
     18071 Granada
     SPAIN
;
_publ_contact_author_email       mquiros@ugr.es
_publ_contact_author_fax         34-58-248526
_publ_contact_author_name        'Miguel Quirós'
_publ_contact_author_phone       34-58-240441
_journal_name_full               Polyhedron
_journal_page_first              372
_journal_page_last               378
_journal_paper_doi               10.1016/j.poly.2009.06.002
_journal_volume                  29
_journal_year                    2010
_chemical_formula_moiety         'C16 H28 Cu N14 O4, 2 (H2 O)'
_chemical_formula_sum            'C16 H32 Cu N14 O6'
_chemical_formula_weight         580.10
_chemical_name_systematic
; 
 ? 
;
_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     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                108.819(1)
_cell_angle_beta                 96.302(1)
_cell_angle_gamma                97.634(1)
_cell_formula_units_Z            1
_cell_length_a                   7.5499(6)
_cell_length_b                   8.1885(6)
_cell_length_c                   10.9247(9)
_cell_measurement_reflns_used    2826
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.2
_cell_measurement_theta_min      2.7
_cell_volume                     625.18(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART (Bruker, 1999)'
_computing_data_reduction        'Bruker SAINT (Bruker, 1999)'
_computing_molecular_graphics    'Xtal_GX (Hall & du Boulay, 1997)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997b)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_device_type  'Bruker SMART APEX CCD system'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0126
_diffrn_reflns_av_sigmaI/netI    0.0243
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3961
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.20
_diffrn_reflns_theta_min         2.00
_diffrn_standards_decay_%        1.1
_diffrn_standards_number         204
_exptl_absorpt_coefficient_mu    0.936
_exptl_absorpt_correction_T_max  0.850
_exptl_absorpt_correction_T_min  0.688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             303
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2679
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0303
_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)+(0.0400P)²+0.4000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0787
_reflns_number_gt                2579
_reflns_number_total             2679
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cuendmax.cif
_cod_data_source_block           cuendmax
_cod_database_code               1500029
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Cu Cu 0.5000 0.5000 0.5000 0.01472(10) Uani 1 2 d S . .
N1 N 0.32670(19) 0.40219(18) 0.66906(14) 0.0168(3) Uani 1 1 d . . .
N2 N 0.2469(2) 0.23594(19) 0.63026(14) 0.0181(3) Uani 1 1 d . . .
N3 N 0.1819(2) 0.19187(19) 0.72961(14) 0.0182(3) Uani 1 1 d . . .
C3A C 0.2251(2) 0.3385(2) 0.83347(16) 0.0156(3) Uani 1 1 d . . .
N4 N 0.1918(2) 0.36377(19) 0.95955(14) 0.0180(3) Uani 1 1 d . . .
C4 C 0.1105(3) 0.2182(3) 0.99739(19) 0.0255(4) Uani 1 1 d . . .
H41 H 0.2031 0.1873 1.0520 0.031 Uiso 1 1 d R . .
H42 H 0.0610 0.1165 0.9184 0.031 Uiso 1 1 d R . .
H43 H 0.0129 0.2531 1.0469 0.031 Uiso 1 1 d R . .
C5 C 0.2407(2) 0.5283(2) 1.05237(17) 0.0178(3) Uani 1 1 d . . .
O5 O 0.20808(18) 0.55970(18) 1.16422(12) 0.0248(3) Uani 1 1 d . . .
N6 N 0.3298(2) 0.66135(19) 1.01504(14) 0.0170(3) Uani 1 1 d . . .
C6 C 0.3813(3) 0.8350(2) 1.11900(17) 0.0236(4) Uani 1 1 d . . .
H61 H 0.2764 0.8659 1.1610 0.028 Uiso 1 1 d R . .
H62 H 0.4230 0.9229 1.0804 0.028 Uiso 1 1 d R . .
H63 H 0.4791 0.8316 1.1845 0.028 Uiso 1 1 d R . .
C7 C 0.3744(2) 0.6451(2) 0.89029(16) 0.0170(3) Uani 1 1 d . . .
O7 O 0.45450(19) 0.77106(16) 0.86896(13) 0.0245(3) Uani 1 1 d . . .
C7A C 0.3146(2) 0.4709(2) 0.79883(16) 0.0153(3) Uani 1 1 d . . .
N1E N 0.48360(19) 0.75323(18) 0.59323(14) 0.0166(3) Uani 1 1 d . . .
H11E H 0.4599 0.7682 0.6766 0.020 Uiso 1 1 d R . .
H12E H 0.5911 0.8251 0.5992 0.020 Uiso 1 1 d R . .
C1E C 0.3348(2) 0.7974(2) 0.51656(19) 0.0210(4) Uani 1 1 d . . .
H13E H 0.3766 0.8210 0.4401 0.025 Uiso 1 1 d R . .
H14E H 0.2945 0.9034 0.5715 0.025 Uiso 1 1 d R . .
C2E C 0.1808(2) 0.6419(2) 0.47137(19) 0.0214(4) Uani 1 1 d . . .
H23E H 0.1299 0.6266 0.5475 0.026 Uiso 1 1 d R . .
H24E H 0.0832 0.6607 0.4117 0.026 Uiso 1 1 d R . .
N2E N 0.25428(19) 0.48495(18) 0.40204(14) 0.0162(3) Uani 1 1 d . . .
H21E H 0.2629 0.4803 0.3177 0.019 Uiso 1 1 d R . .
H22E H 0.1787 0.3851 0.3984 0.019 Uiso 1 1 d R . .
O1W O 0.11003(19) 0.10330(17) 0.35873(13) 0.0242(3) Uani 1 1 d D . .
H11W H 0.137(3) 0.122(3) 0.4388(11) 0.029 Uiso 1 1 d D . .
H12W H 0.020(2) 0.022(2) 0.333(2) 0.029 Uiso 1 1 d 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
_geom_angle_publ_flag
N2E Cu N2E 180.0 . 2_666 ?
N2E Cu N1E 85.15(6) . . ?
N2E Cu N1E 94.85(6) 2_666 . ?
N2E Cu N1E 94.85(6) . 2_666 ?
N2E Cu N1E 85.15(6) 2_666 2_666 ?
N1E Cu N1E 180.000(2) . 2_666 ?
N2E Cu N1 93.79(5) . 2_666 ?
N2E Cu N1 86.21(5) 2_666 2_666 ?
N1E Cu N1 89.23(5) . 2_666 ?
N1E Cu N1 90.77(5) 2_666 2_666 ?
N2E Cu N1 86.21(5) . . ?
N2E Cu N1 93.79(5) 2_666 . ?
N1E Cu N1 90.77(5) . . ?
N1E Cu N1 89.23(5) 2_666 . ?
N1 Cu N1 180.0 2_666 . ?
N2 N1 C7A 105.90(14) . . ?
N2 N1 Cu 116.50(10) . . ?
C7A N1 Cu 136.84(11) . . ?
N1 N2 N3 112.26(13) . . ?
C3A N3 N2 104.82(14) . . ?
N3 C3A C7A 109.66(15) . . ?
N3 C3A N4 128.02(16) . . ?
C7A C3A N4 122.31(15) . . ?
C5 N4 C3A 119.14(15) . . ?
C5 N4 C4 119.25(15) . . ?
C3A N4 C4 121.59(15) . . ?
N4 C4 H41 109.5 . . ?
N4 C4 H42 109.3 . . ?
H41 C4 H42 109.5 . . ?
N4 C4 H43 109.6 . . ?
H41 C4 H43 109.5 . . ?
H42 C4 H43 109.5 . . ?
O5 C5 N4 121.94(17) . . ?
O5 C5 N6 120.41(16) . . ?
N4 C5 N6 117.65(15) . . ?
C5 N6 C7 126.68(14) . . ?
C5 N6 C6 115.40(14) . . ?
C7 N6 C6 117.92(14) . . ?
N6 C6 H61 109.6 . . ?
N6 C6 H62 109.3 . . ?
H61 C6 H62 109.5 . . ?
N6 C6 H63 109.5 . . ?
H61 C6 H63 109.5 . . ?
H62 C6 H63 109.5 . . ?
O7 C7 N6 121.04(15) . . ?
O7 C7 C7A 126.95(16) . . ?
N6 C7 C7A 112.01(15) . . ?
N1 C7A C3A 107.36(15) . . ?
N1 C7A C7 130.50(16) . . ?
C3A C7A C7 122.13(15) . . ?
C1E N1E Cu 107.65(10) . . ?
C1E N1E H11E 110.1 . . ?
Cu N1E H11E 110.1 . . ?
C1E N1E H12E 110.2 . . ?
Cu N1E H12E 110.3 . . ?
H11E N1E H12E 108.5 . . ?
N1E C1E C2E 107.42(14) . . ?
N1E C1E H13E 110.1 . . ?
C2E C1E H13E 110.2 . . ?
N1E C1E H14E 110.3 . . ?
C2E C1E H14E 110.3 . . ?
H13E C1E H14E 108.5 . . ?
N2E C2E C1E 107.61(14) . . ?
N2E C2E H23E 110.2 . . ?
C1E C2E H23E 110.2 . . ?
N2E C2E H24E 110.1 . . ?
C1E C2E H24E 110.1 . . ?
H23E C2E H24E 108.5 . . ?
C2E N2E Cu 108.30(11) . . ?
C2E N2E H21E 110.1 . . ?
Cu N2E H21E 110.0 . . ?
C2E N2E H22E 110.0 . . ?
Cu N2E H22E 110.0 . . ?
H21E N2E H22E 108.4 . . ?
H11W O1W H12W 105(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu N2E 2.0051(14) . ?
Cu N2E 2.0052(14) 2_666 ?
Cu N1E 2.0213(14) . ?
Cu N1E 2.0214(14) 2_666 ?
Cu N1 2.6402(14) 2_666 ?
Cu N1 2.6402(14) . ?
N1 N2 1.323(2) . ?
N1 C7A 1.365(2) . ?
N2 N3 1.368(2) . ?
N3 C3A 1.331(2) . ?
C3A C7A 1.379(2) . ?
C3A N4 1.382(2) . ?
N4 C5 1.372(2) . ?
N4 C4 1.466(2) . ?
C4 H41 0.9801 . ?
C4 H42 0.9801 . ?
C4 H43 0.9801 . ?
C5 O5 1.225(2) . ?
C5 N6 1.400(2) . ?
N6 C7 1.408(2) . ?
N6 C6 1.475(2) . ?
C6 H61 0.9800 . ?
C6 H62 0.9800 . ?
C6 H63 0.9800 . ?
C7 O7 1.227(2) . ?
C7 C7A 1.431(2) . ?
N1E C1E 1.480(2) . ?
N1E H11E 0.9200 . ?
N1E H12E 0.9200 . ?
C1E C2E 1.514(3) . ?
C1E H13E 0.9900 . ?
C1E H14E 0.9900 . ?
C2E N2E 1.479(2) . ?
C2E H23E 0.9900 . ?
C2E H24E 0.9900 . ?
N2E H21E 0.9200 . ?
N2E H22E 0.9200 . ?
O1W H11W 0.834(10) . ?
O1W H12W 0.836(10) . ?
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
N1E H11E O7 0.92 2.10 3.0023(19) 167.0 .
N1E H12E O1W 0.92 2.21 3.0593(19) 152.8 2_666
N2E H21E O5 0.92 2.01 2.8514(19) 151.9 1_554
N2E H22E O1W 0.92 2.18 3.0340(19) 153.3 .
O1W H11W N2 0.834(10) 2.022(12) 2.828(2) 162(2) .
O1W H12W N3 0.836(10) 2.038(10) 2.871(2) 174(2) 2_556
