#------------------------------------------------------------------------------
#$Date: 2016-03-25 10:31:10 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179752 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/48/7004812.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_7004812
loop_
_publ_author_name
'Scott, Lauren E.'
'Page, Brent D. G.'
'Patrick, Brian O.'
'Orvig, Chris'
_publ_section_title
;
 Altering pyridinone N-substituents to optimise activity as potential
 prodrugs for Alzheimer's disease
;
_journal_issue                   45
_journal_name_full               'Dalton Transactions'
_journal_page_first              6364
_journal_page_last               6367
_journal_paper_doi               10.1039/b815404j
_journal_year                    2008
_chemical_formula_sum            'C28 H26 Cl6 Cu N2 O4'
_chemical_formula_weight         730.75
_chemical_name_common            Cu(nbp)2
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.787(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.3840(3)
_cell_length_b                   21.0223(12)
_cell_length_c                   11.7249(7)
_cell_measurement_reflns_used    4397
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.17
_cell_measurement_theta_min      2.61
_cell_volume                     1562.53(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'area detector'
_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  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13415
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    1.249
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_correction_T_min  0.745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker Nonius, 2003)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             742
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3545
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0529
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0419P)²+2.3856P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1338
_reflns_number_gt                2533
_reflns_number_total             3545
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b815404j.txt
_cod_data_source_block           co340
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7004812
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1 C 0.4803(8) -0.1418(2) 0.7068(4) 0.0851(15) Uani 1 1 d . . .
H1A H 0.5629 -0.1662 0.6565 0.128 Uiso 1 1 calc R . .
H1B H 0.3307 -0.1528 0.6895 0.128 Uiso 1 1 calc R . .
H1C H 0.5283 -0.1521 0.7871 0.128 Uiso 1 1 calc R . .
C2 C 0.5088(7) -0.0733(2) 0.6874(3) 0.0646(11) Uani 1 1 d . A .
C3 C 0.3482(6) -0.03758(19) 0.6273(3) 0.0527(9) Uani 1 1 d . . .
C4 C 0.3766(7) 0.02759(18) 0.6074(3) 0.0541(9) Uani 1 1 d . . .
C5 C 0.5746(7) 0.0558(2) 0.6503(3) 0.0648(11) Uani 1 1 d . . .
H5 H 0.6003 0.0998 0.6396 0.078 Uiso 1 1 calc R . .
C6 C 0.7235(8) 0.0180(3) 0.7066(3) 0.0751(13) Uani 1 1 d . A .
H6 H 0.8558 0.0365 0.7339 0.090 Uiso 1 1 calc R . .
C7 C 0.856(5) -0.0836(14) 0.789(3) 0.061(4) Uani 0.50 1 d P A 1
H7A H 0.9963 -0.0641 0.7844 0.073 Uiso 0.50 1 calc PR A 1
H7B H 0.8555 -0.1259 0.7518 0.073 Uiso 0.50 1 calc PR A 1
C7B C 0.894(6) -0.0687(17) 0.791(3) 0.107(11) Uani 0.50 1 d P A 2
H7B1 H 1.0090 -0.0380 0.7837 0.128 Uiso 0.50 1 calc PR A 2
H7B2 H 0.9319 -0.1093 0.7559 0.128 Uiso 0.50 1 calc PR A 2
C8 C 0.827(3) -0.0922(10) 0.910(2) 0.045(4) Uani 0.50 1 d P A 1
C8B C 0.877(3) -0.0804(14) 0.923(2) 0.071(6) Uani 0.50 1 d P A 2
C9 C 0.6596(13) -0.0754(5) 0.9610(7) 0.058(2) Uani 0.50 1 d P A 1
H9 H 0.5450 -0.0552 0.9161 0.070 Uiso 0.50 1 calc PR A 1
C9B C 0.7558(18) -0.0383(6) 0.9820(8) 0.082(3) Uani 0.50 1 d P A 2
H9B H 0.6906 -0.0019 0.9454 0.098 Uiso 0.50 1 calc PR A 2
C10 C 0.6450(16) -0.0863(5) 1.0765(8) 0.065(3) Uani 0.50 1 d P A 1
H10 H 0.5174 -0.0779 1.1080 0.078 Uiso 0.50 1 calc PR A 1
C10B C 0.7356(19) -0.0526(7) 1.0956(8) 0.090(4) Uani 0.50 1 d P A 2
H10B H 0.6649 -0.0238 1.1403 0.108 Uiso 0.50 1 calc PR A 2
C11 C 0.8194(8) -0.1096(3) 1.1451(4) 0.0788(13) Uani 0.50 1 d P A 1
H11 H 0.8190 -0.1090 1.2261 0.095 Uiso 0.50 1 calc PR A 1
C11B C 0.8194(8) -0.1096(3) 1.1451(4) 0.0788(13) Uani 0.50 1 d P A 2
H11B H 0.7897 -0.1236 1.2185 0.095 Uiso 0.50 1 calc PR A 2
C12 C 1.001(4) -0.1346(14) 1.099(2) 0.065(5) Uani 0.50 1 d P A 1
H12 H 1.1045 -0.1584 1.1454 0.078 Uiso 0.50 1 calc PR A 1
C12B C 0.937(4) -0.1409(13) 1.086(3) 0.064(5) Uani 0.50 1 d P A 2
H12B H 1.0180 -0.1747 1.1222 0.077 Uiso 0.50 1 calc PR A 2
C13 C 1.020(2) -0.1230(12) 0.986(2) 0.057(4) Uani 0.50 1 d P A 1
H13 H 1.1461 -0.1333 0.9540 0.069 Uiso 0.50 1 calc PR A 1
C13B C 0.954(2) -0.1291(11) 0.9713(19) 0.049(3) Uani 0.50 1 d P A 2
H13B H 1.0251 -0.1588 0.9286 0.059 Uiso 0.50 1 calc PR A 2
C14 C 0.4454(6) 0.69923(18) 0.9826(4) 0.0680(12) Uani 1 1 d . . .
H14 H 0.4433 0.6526 0.9990 0.082 Uiso 1 1 calc R . .
N1 N 0.6955(5) -0.04401(19) 0.7262(2) 0.0627(9) Uani 1 1 d . . .
O1 O 0.2242(4) 0.05829(11) 0.5512(2) 0.0534(6) Uani 1 1 d . . .
O2 O 0.1631(4) -0.06379(11) 0.5851(2) 0.0545(6) Uani 1 1 d . . .
Cu1 Cu 0.0000 0.0000 0.5000 0.04354(18) Uani 1 2 d S . .
Cl1 Cl 0.6560(2) 0.71536(7) 0.90670(17) 0.1218(7) Uani 1 1 d . . .
Cl2 Cl 0.4681(3) 0.74049(7) 1.11314(16) 0.1142(6) Uani 1 1 d . . .
Cl3 Cl 0.2110(2) 0.71962(7) 0.89943(18) 0.1184(6) Uani 1 1 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'
Cl Cl 0.1484 0.1585 '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
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 119.1(4) . . ?
N1 C2 C1 120.4(4) . . ?
C3 C2 C1 120.5(4) . . ?
O2 C3 C2 121.9(4) . . ?
O2 C3 C4 117.6(3) . . ?
C2 C3 C4 120.5(4) . . ?
O1 C4 C3 118.1(4) . . ?
O1 C4 C5 123.8(4) . . ?
C3 C4 C5 118.1(4) . . ?
C6 C5 C4 117.9(4) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
N1 C6 C5 123.8(5) . . ?
N1 C6 H6 118.1 . . ?
C5 C6 H6 118.1 . . ?
N1 C7 C8 114(2) . . ?
N1 C7 H7A 108.8 . . ?
C8 C7 H7A 108.9 . . ?
N1 C7 H7B 108.8 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
N1 C7B C8B 114(2) . . ?
N1 C7B H7B1 108.9 . . ?
C8B C7B H7B1 108.8 . . ?
N1 C7B H7B2 108.8 . . ?
C8B C7B H7B2 108.8 . . ?
H7B1 C7B H7B2 107.7 . . ?
C9 C8 C7 127(2) . . ?
C9 C8 C13 118.5(19) . . ?
C7 C8 C13 115(2) . . ?
C13B C8B C9B 120(2) . . ?
C13B C8B C7B 120(2) . . ?
C9B C8B C7B 119(3) . . ?
C8 C9 C10 122.8(13) . . ?
C8 C9 H9 118.6 . . ?
C10 C9 H9 118.6 . . ?
C10B C9B C8B 116.9(15) . . ?
C10B C9B H9B 121.5 . . ?
C8B C9B H9B 121.6 . . ?
C11 C10 C9 118.9(8) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C9B C10B H10B 119.8 . . ?
C10 C11 C12 122.6(11) . . ?
C10 C11 H11 118.7 . . ?
C12 C11 H11 118.7 . . ?
C13 C12 C11 118(2) . . ?
C13 C12 H12 121.0 . . ?
C11 C12 H12 120.9 . . ?
C13B C12B H12B 118.0 . . ?
C12 C13 C8 117.7(18) . . ?
C12 C13 H13 121.1 . . ?
C8 C13 H13 121.2 . . ?
C8B C13B C12B 121(2) . . ?
C8B C13B H13B 119.4 . . ?
C12B C13B H13B 119.5 . . ?
Cl1 C14 Cl3 109.4(3) . . ?
Cl1 C14 Cl2 111.3(2) . . ?
Cl3 C14 Cl2 110.2(2) . . ?
Cl1 C14 H14 108.6 . . ?
Cl3 C14 H14 108.6 . . ?
Cl2 C14 H14 108.6 . . ?
C6 N1 C2 120.5(4) . . ?
C6 N1 C7 123.0(12) . . ?
C2 N1 C7 116.5(12) . . ?
C6 N1 C7B 107.7(14) . . ?
C2 N1 C7B 131.8(14) . . ?
C7 N1 C7B 15(2) . . ?
C4 O1 Cu1 109.3(2) . . ?
C3 O2 Cu1 107.8(2) . . ?
O2 Cu1 O2 180.00(13) . 3_556 ?
O2 Cu1 O1 93.17(11) . 3_556 ?
O2 Cu1 O1 86.83(11) 3_556 3_556 ?
O2 Cu1 O1 86.83(11) . . ?
O2 Cu1 O1 93.17(11) 3_556 . ?
O1 Cu1 O1 180.00(11) 3_556 . ?
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
C1 C2 1.474(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.370(6) . ?
C2 C3 1.393(5) . ?
C3 O2 1.344(5) . ?
C3 C4 1.405(5) . ?
C4 O1 1.283(5) . ?
C4 C5 1.433(6) . ?
C5 C6 1.350(6) . ?
C5 H5 0.9500 . ?
C6 N1 1.340(6) . ?
C6 H6 0.9500 . ?
C7 N1 1.45(4) . ?
C7 C8 1.47(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7B N1 1.49(4) . ?
C7B C8B 1.59(5) . ?
C7B H7B1 0.9900 . ?
C7B H7B2 0.9900 . ?
C8 C9 1.33(2) . ?
C8 C13 1.57(3) . ?
C8B C13B 1.24(4) . ?
C8B C9B 1.41(3) . ?
C9 C10 1.387(12) . ?
C9 H9 0.9500 . ?
C9B C10B 1.386(13) . ?
C9B H9B 0.9500 . ?
C10 C11 1.384(12) . ?
C10 H10 0.9500 . ?
C10B H10B 0.9500 . ?
C11 C12 1.44(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.37(4) . ?
C12 H12 0.9500 . ?
C12B C13B 1.38(4) . ?
C12B H12B 0.9500 . ?
C13 H13 0.9500 . ?
C13B H13B 0.9500 . ?
C14 Cl1 1.731(4) . ?
C14 Cl3 1.740(5) . ?
C14 Cl2 1.750(5) . ?
C14 H14 1.0000 . ?
O1 Cu1 1.925(2) . ?
O2 Cu1 1.906(2) . ?
Cu1 O2 1.906(2) 3_556 ?
Cu1 O1 1.925(2) 3_556 ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 O2 178.7(3) . . . . ?
C1 C2 C3 O2 0.1(5) . . . . ?
N1 C2 C3 C4 -0.5(5) . . . . ?
C1 C2 C3 C4 -179.0(3) . . . . ?
O2 C3 C4 O1 0.6(4) . . . . ?
C2 C3 C4 O1 179.7(3) . . . . ?
O2 C3 C4 C5 -179.0(3) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
O1 C4 C5 C6 -178.9(3) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
C4 C5 C6 N1 -1.2(5) . . . . ?
N1 C7 C8 C9 10(3) . . . . ?
N1 C7 C8 C13 -168.5(17) . . . . ?
N1 C7B C8B C13B 137(2) . . . . ?
N1 C7B C8B C9B -36(3) . . . . ?
C7 C8 C9 C10 179.1(18) . . . . ?
C13 C8 C9 C10 -3(2) . . . . ?
C13B C8B C9B C10B 3(3) . . . . ?
C7B C8B C9B C10B 176.3(18) . . . . ?
C8 C9 C10 C11 6.7(18) . . . . ?
C9 C10 C11 C12 -12.4(18) . . . . ?
C10 C11 C12 C13 14(3) . . . . ?
C11 C12 C13 C8 -9(3) . . . . ?
C9 C8 C13 C12 4(3) . . . . ?
C7 C8 C13 C12 -178(2) . . . . ?
C9B C8B C13B C12B -5(3) . . . . ?
C7B C8B C13B C12B -178(2) . . . . ?
C5 C6 N1 C2 0.9(5) . . . . ?
C5 C6 N1 C7 -178.7(14) . . . . ?
C5 C6 N1 C7B -179.5(14) . . . . ?
C3 C2 N1 C6 0.0(5) . . . . ?
C1 C2 N1 C6 178.6(4) . . . . ?
C3 C2 N1 C7 179.6(13) . . . . ?
C1 C2 N1 C7 -1.9(14) . . . . ?
C3 C2 N1 C7B -179.5(18) . . . . ?
C1 C2 N1 C7B -0.9(19) . . . . ?
C8 C7 N1 C6 97.7(19) . . . . ?
C8 C7 N1 C2 -82(2) . . . . ?
C8 C7 N1 C7B 101(10) . . . . ?
C8B C7B N1 C6 105(2) . . . . ?
C8B C7B N1 C2 -76(3) . . . . ?
C8B C7B N1 C7 -73(9) . . . . ?
C3 C4 O1 Cu1 -4.3(3) . . . . ?
C5 C4 O1 Cu1 175.3(3) . . . . ?
C2 C3 O2 Cu1 -175.7(2) . . . . ?
C4 C3 O2 Cu1 3.5(3) . . . . ?
C3 O2 Cu1 O2 71(100) . . . 3_556 ?
C3 O2 Cu1 O1 175.5(2) . . . 3_556 ?
C3 O2 Cu1 O1 -4.5(2) . . . . ?
C4 O1 Cu1 O2 4.9(2) . . . . ?
C4 O1 Cu1 O2 -175.1(2) . . . 3_556 ?
C4 O1 Cu1 O1 165(59) . . . 3_556 ?
