#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/00/1500028.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_1500028
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         'C18 H29 Cu N13 O4'
_chemical_formula_sum            'C18 H29 Cu N13 O4'
_chemical_formula_weight         555.08
_chemical_name_systematic
; 
 ? 
;
_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     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.298(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4355(6)
_cell_length_b                   40.985(3)
_cell_length_c                   7.1685(5)
_cell_measurement_reflns_used    5063
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      2.6
_cell_volume                     2276.3(3)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.934
_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  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       53
_diffrn_reflns_limit_k_min       -54
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            26461
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         1.99
_diffrn_standards_decay_%        0.0
_diffrn_standards_number         426
_exptl_absorpt_coefficient_mu    1.017
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1156
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.255
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.255
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0300P)²+2.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1121
_reflns_number_gt                4848
_reflns_number_total             5334
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cubapadmax.cif
_cod_data_source_block           cutrenax
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1500028
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_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 0.11762(4) 0.377801(7) 0.35923(5) 0.03240(11) Uani 1 1 d . . .
N1A N 0.3507(3) 0.42991(5) 0.6161(4) 0.0351(5) Uani 1 1 d . . .
N2A N 0.2028(3) 0.42300(5) 0.4636(4) 0.0359(5) Uani 1 1 d . . .
N3A N 0.1122(3) 0.44999(5) 0.3677(4) 0.0359(5) Uani 1 1 d . . .
C3AA C 0.2123(3) 0.47459(6) 0.4681(4) 0.0307(5) Uani 1 1 d . . .
N4A N 0.1788(3) 0.50744(5) 0.4306(4) 0.0328(5) Uani 1 1 d . . .
C4A C 0.0288(4) 0.51884(7) 0.2551(5) 0.0404(7) Uani 1 1 d . . .
H41A H -0.0247 0.5366 0.2956 0.049 Uiso 1 1 d R . .
H42A H -0.0525 0.5013 0.2038 0.049 Uiso 1 1 d R . .
H43A H 0.0652 0.5261 0.1510 0.049 Uiso 1 1 d R . .
C5A C 0.2974(4) 0.52970(6) 0.5479(4) 0.0335(6) Uani 1 1 d . . .
O5A O 0.2739(3) 0.55904(5) 0.5200(3) 0.0427(5) Uani 1 1 d . . .
N6A N 0.4471(3) 0.51757(5) 0.7013(3) 0.0330(5) Uani 1 1 d . . .
C6A C 0.5709(4) 0.54211(7) 0.8248(5) 0.0401(7) Uani 1 1 d . . .
H61A H 0.5942 0.5574 0.7374 0.048 Uiso 1 1 d R . .
H62A H 0.6762 0.5315 0.9099 0.048 Uiso 1 1 d R . .
H63A H 0.5234 0.5534 0.9080 0.048 Uiso 1 1 d R . .
C7A C 0.4922(4) 0.48453(6) 0.7503(4) 0.0324(6) Uani 1 1 d . . .
O7A O 0.6285(3) 0.47716(5) 0.8856(3) 0.0433(5) Uani 1 1 d . . .
C7AA C 0.3591(3) 0.46298(6) 0.6206(4) 0.0311(5) Uani 1 1 d . . .
N1B N -0.1231(3) 0.32465(5) 0.3884(4) 0.0360(5) Uani 1 1 d . . .
N2B N 0.0348(3) 0.33143(5) 0.4086(4) 0.0361(5) Uani 1 1 d . . .
N3B N 0.1340(3) 0.30422(5) 0.4263(4) 0.0362(5) Uani 1 1 d . . .
C3AB C 0.0268(3) 0.27979(6) 0.4145(4) 0.0311(5) Uani 1 1 d . . .
N4B N 0.0621(3) 0.24678(5) 0.4190(4) 0.0351(5) Uani 1 1 d . . .
C4B C 0.2317(4) 0.23491(7) 0.4405(5) 0.0446(7) Uani 1 1 d . . .
H41B H 0.2929 0.2268 0.5757 0.054 Uiso 1 1 d R . .
H42B H 0.2960 0.2525 0.4153 0.054 Uiso 1 1 d R . .
H43B H 0.2178 0.2177 0.3444 0.054 Uiso 1 1 d R . .
C5B C -0.0657(4) 0.22488(6) 0.4008(4) 0.0359(6) Uani 1 1 d . . .
O5B O -0.0424(3) 0.19558(5) 0.4015(4) 0.0498(6) Uani 1 1 d . . .
N6B N -0.2266(3) 0.23742(5) 0.3806(4) 0.0367(5) Uani 1 1 d . . .
C6B C -0.3619(4) 0.21315(8) 0.3548(5) 0.0505(8) Uani 1 1 d . . .
H61B H -0.3839 0.2008 0.2332 0.061 Uiso 1 1 d R . .
H62B H -0.4657 0.2241 0.3445 0.061 Uiso 1 1 d R . .
H63B H -0.3246 0.1987 0.4695 0.061 Uiso 1 1 d R . .
C7B C -0.2723(4) 0.27060(7) 0.3791(4) 0.0346(6) Uani 1 1 d . . .
O7B O -0.4148(3) 0.27836(5) 0.3661(4) 0.0491(6) Uani 1 1 d . . .
C7AB C -0.1316(3) 0.29149(6) 0.3931(4) 0.0320(6) Uani 1 1 d . . .
N1E N -0.1273(3) 0.39244(5) 0.2744(4) 0.0380(5) Uani 1 1 d . . .
H11E H -0.1882 0.3751 0.2859 0.046 Uiso 1 1 d R . .
H12E H -0.1291 0.4072 0.3663 0.046 Uiso 1 1 d R . .
C2E C -0.2226(4) 0.40665(8) 0.0716(5) 0.0507(8) Uani 1 1 d . . .
H21E H -0.1801 0.4286 0.0691 0.061 Uiso 1 1 d R . .
H22E H -0.3435 0.4083 0.0489 0.061 Uiso 1 1 d R . .
C3E C -0.2071(5) 0.38725(9) -0.0995(5) 0.0565(9) Uani 1 1 d . . .
H31E H -0.2355 0.3647 -0.0859 0.068 Uiso 1 1 d R . .
H32E H -0.2920 0.3953 -0.2271 0.068 Uiso 1 1 d R . .
C4E C -0.0329(5) 0.38820(9) -0.1096(5) 0.0568(9) Uani 1 1 d . . .
H41E H -0.0432 0.3800 -0.2408 0.068 Uiso 1 1 d R . .
H42E H 0.0047 0.4107 -0.0996 0.068 Uiso 1 1 d R . .
N5E N 0.1005(3) 0.36916(5) 0.0514(4) 0.0353(5) Uani 1 1 d . . .
H5E H 0.0638 0.3481 0.0247 0.042 Uiso 1 1 d R . .
C6E C 0.2629(4) 0.36988(8) 0.0205(5) 0.0505(8) Uani 1 1 d . . .
H61E H 0.3005 0.3923 0.0255 0.061 Uiso 1 1 d R . .
H62E H 0.2417 0.3614 -0.1137 0.061 Uiso 1 1 d R . .
C7E C 0.4055(4) 0.35027(9) 0.1759(6) 0.0531(9) Uani 1 1 d . . .
H71E H 0.4978 0.3478 0.1286 0.064 Uiso 1 1 d R . .
H72E H 0.3613 0.3286 0.1828 0.064 Uiso 1 1 d R . .
C8E C 0.4807(4) 0.36425(7) 0.3875(5) 0.0452(7) Uani 1 1 d . . .
H81E H 0.5878 0.3530 0.4658 0.054 Uiso 1 1 d R . .
H82E H 0.5071 0.3871 0.3806 0.054 Uiso 1 1 d R . .
N9E N 0.3618(3) 0.36099(6) 0.4913(4) 0.0408(6) Uani 1 1 d . . .
H91E H 0.4114 0.3710 0.6125 0.049 Uiso 1 1 d R . .
H92E H 0.3555 0.3396 0.5165 0.049 Uiso 1 1 d R . .
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
N1E Cu N9E 169.95(11) . . ?
N1E Cu N2A 90.61(9) . . ?
N9E Cu N2A 89.55(10) . . ?
N1E Cu N2B 87.16(9) . . ?
N9E Cu N2B 87.57(9) . . ?
N2A Cu N2B 149.26(10) . . ?
N1E Cu N5E 95.37(10) . . ?
N9E Cu N5E 93.79(10) . . ?
N2A Cu N5E 113.26(9) . . ?
N2B Cu N5E 97.47(9) . . ?
N2A N1A C7AA 104.9(2) . . ?
N1A N2A N3A 113.6(2) . . ?
N1A N2A Cu 125.63(18) . . ?
N3A N2A Cu 120.67(17) . . ?
C3AA N3A N2A 103.5(2) . . ?
N3A C3AA C7AA 110.4(2) . . ?
N3A C3AA N4A 126.7(2) . . ?
C7AA C3AA N4A 123.0(2) . . ?
C5A N4A C3AA 119.1(2) . . ?
C5A N4A C4A 119.2(2) . . ?
C3AA N4A C4A 121.3(2) . . ?
N4A C4A H41A 109.4 . . ?
N4A C4A H42A 109.5 . . ?
H41A C4A H42A 109.5 . . ?
N4A C4A H43A 109.5 . . ?
H41A C4A H43A 109.5 . . ?
H42A C4A H43A 109.5 . . ?
O5A C5A N4A 121.6(3) . . ?
O5A C5A N6A 121.1(3) . . ?
N4A C5A N6A 117.4(2) . . ?
C5A N6A C7A 127.4(2) . . ?
C5A N6A C6A 115.9(2) . . ?
C7A N6A C6A 116.7(2) . . ?
N6A C6A H61A 109.5 . . ?
N6A C6A H62A 109.4 . . ?
H61A C6A H62A 109.5 . . ?
N6A C6A H63A 109.5 . . ?
H61A C6A H63A 109.5 . . ?
H62A C6A H63A 109.5 . . ?
O7A C7A N6A 121.0(2) . . ?
O7A C7A C7AA 127.8(3) . . ?
N6A C7A C7AA 111.2(2) . . ?
N1A C7AA C3AA 107.8(2) . . ?
N1A C7AA C7A 130.3(2) . . ?
C3AA C7AA C7A 121.9(2) . . ?
N2B N1B C7AB 105.6(2) . . ?
N1B N2B N3B 113.2(2) . . ?
N1B N2B Cu 124.28(17) . . ?
N3B N2B Cu 121.35(17) . . ?
C3AB N3B N2B 103.4(2) . . ?
N3B C3AB C7AB 110.6(2) . . ?
N3B C3AB N4B 126.9(2) . . ?
C7AB C3AB N4B 122.5(2) . . ?
C5B N4B C3AB 119.0(2) . . ?
C5B N4B C4B 119.6(2) . . ?
C3AB N4B C4B 121.4(2) . . ?
N4B C4B H41B 109.6 . . ?
N4B C4B H42B 109.4 . . ?
H41B C4B H42B 109.5 . . ?
N4B C4B H43B 109.4 . . ?
H41B C4B H43B 109.5 . . ?
H42B C4B H43B 109.5 . . ?
O5B C5B N4B 121.8(3) . . ?
O5B C5B N6B 120.6(3) . . ?
N4B C5B N6B 117.6(2) . . ?
C5B N6B C7B 127.1(2) . . ?
C5B N6B C6B 115.9(2) . . ?
C7B N6B C6B 117.1(2) . . ?
N6B C6B H61B 109.4 . . ?
N6B C6B H62B 109.4 . . ?
H61B C6B H62B 109.5 . . ?
N6B C6B H63B 109.5 . . ?
H61B C6B H63B 109.5 . . ?
H62B C6B H63B 109.5 . . ?
O7B C7B N6B 120.9(3) . . ?
O7B C7B C7AB 128.1(3) . . ?
N6B C7B C7AB 111.0(2) . . ?
N1B C7AB C3AB 107.1(2) . . ?
N1B C7AB C7B 130.1(3) . . ?
C3AB C7AB C7B 122.8(2) . . ?
C2E N1E Cu 120.9(2) . . ?
C2E N1E H11E 107.1 . . ?
Cu N1E H11E 107.1 . . ?
C2E N1E H12E 107.2 . . ?
Cu N1E H12E 107.1 . . ?
H11E N1E H12E 106.8 . . ?
N1E C2E C3E 113.8(3) . . ?
N1E C2E H21E 108.8 . . ?
C3E C2E H21E 108.8 . . ?
N1E C2E H22E 108.7 . . ?
C3E C2E H22E 108.9 . . ?
H21E C2E H22E 107.7 . . ?
C4E C3E C2E 115.2(3) . . ?
C4E C3E H31E 108.4 . . ?
C2E C3E H31E 108.4 . . ?
C4E C3E H32E 108.5 . . ?
C2E C3E H32E 108.5 . . ?
H31E C3E H32E 107.5 . . ?
N5E C4E C3E 114.0(3) . . ?
N5E C4E H41E 108.8 . . ?
C3E C4E H41E 108.9 . . ?
N5E C4E H42E 108.7 . . ?
C3E C4E H42E 108.6 . . ?
H41E C4E H42E 107.7 . . ?
C6E N5E C4E 109.8(3) . . ?
C6E N5E Cu 117.09(19) . . ?
C4E N5E Cu 115.5(2) . . ?
C6E N5E H5E 104.3 . . ?
C4E N5E H5E 104.2 . . ?
Cu N5E H5E 104.3 . . ?
N5E C6E C7E 113.4(3) . . ?
N5E C6E H61E 108.9 . . ?
C7E C6E H61E 109.0 . . ?
N5E C6E H62E 108.9 . . ?
C7E C6E H62E 108.8 . . ?
H61E C6E H62E 107.7 . . ?
C8E C7E C6E 115.9(3) . . ?
C8E C7E H71E 108.4 . . ?
C6E C7E H71E 108.3 . . ?
C8E C7E H72E 108.3 . . ?
C6E C7E H72E 108.3 . . ?
H71E C7E H72E 107.4 . . ?
N9E C8E C7E 112.0(3) . . ?
N9E C8E H81E 109.2 . . ?
C7E C8E H81E 109.1 . . ?
N9E C8E H82E 109.2 . . ?
C7E C8E H82E 109.3 . . ?
H81E C8E H82E 107.9 . . ?
C8E N9E Cu 120.3(2) . . ?
C8E N9E H91E 107.3 . . ?
Cu N9E H91E 107.2 . . ?
C8E N9E H92E 107.2 . . ?
Cu N9E H92E 107.2 . . ?
H91E N9E H92E 106.8 . . ?
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 N1E 2.001(2) . ?
Cu N9E 2.017(2) . ?
Cu N2A 2.021(2) . ?
Cu N2B 2.102(2) . ?
Cu N5E 2.183(2) . ?
N1A N2A 1.324(3) . ?
N1A C7AA 1.357(3) . ?
N2A N3A 1.365(3) . ?
N3A C3AA 1.329(3) . ?
C3AA C7AA 1.373(4) . ?
C3AA N4A 1.380(3) . ?
N4A C5A 1.369(3) . ?
N4A C4A 1.464(4) . ?
C4A H41A 0.9599 . ?
C4A H42A 0.9601 . ?
C4A H43A 0.9600 . ?
C5A O5A 1.222(3) . ?
C5A N6A 1.398(4) . ?
N6A C7A 1.413(3) . ?
N6A C6A 1.468(3) . ?
C6A H61A 0.9600 . ?
C6A H62A 0.9600 . ?
C6A H63A 0.9600 . ?
C7A O7A 1.213(3) . ?
C7A C7AA 1.442(4) . ?
N1B N2B 1.312(3) . ?
N1B C7AB 1.362(3) . ?
N2B N3B 1.370(3) . ?
N3B C3AB 1.330(3) . ?
C3AB C7AB 1.370(4) . ?
C3AB N4B 1.383(3) . ?
N4B C5B 1.369(4) . ?
N4B C4B 1.460(4) . ?
C4B H41B 0.9600 . ?
C4B H42B 0.9600 . ?
C4B H43B 0.9600 . ?
C5B O5B 1.217(3) . ?
C5B N6B 1.404(4) . ?
N6B C7B 1.412(3) . ?
N6B C6B 1.469(4) . ?
C6B H61B 0.9600 . ?
C6B H62B 0.9600 . ?
C6B H63B 0.9600 . ?
C7B O7B 1.211(3) . ?
C7B C7AB 1.435(4) . ?
N1E C2E 1.474(4) . ?
N1E H11E 0.9000 . ?
N1E H12E 0.9000 . ?
C2E C3E 1.510(5) . ?
C2E H21E 0.9700 . ?
C2E H22E 0.9700 . ?
C3E C4E 1.501(5) . ?
C3E H31E 0.9700 . ?
C3E H32E 0.9700 . ?
C4E N5E 1.476(4) . ?
C4E H41E 0.9700 . ?
C4E H42E 0.9700 . ?
N5E C6E 1.472(4) . ?
N5E H5E 0.9100 . ?
C6E C7E 1.508(5) . ?
C6E H61E 0.9700 . ?
C6E H62E 0.9700 . ?
C7E C8E 1.507(5) . ?
C7E H71E 0.9700 . ?
C7E H72E 0.9700 . ?
C8E N9E 1.473(4) . ?
C8E H81E 0.9700 . ?
C8E H82E 0.9700 . ?
N9E H91E 0.9000 . ?
N9E H92E 0.9000 . ?
