#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/34/4303485.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_4303485
loop_
_publ_author_name
'Miguel A. Galindo'
'David Amantia'
'Alberto Martinez Martinez'
'William Clegg'
'Ross W. Harrington'
'Virtudes Moreno Martinez'
'Andrew Houlton'
_publ_section_title
;
Probing Metal-Ion Purine Interactions at DNA Minor-Groove Sites
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              10295
_journal_page_last               10303
_journal_paper_doi               10.1021/ic9013448
_journal_volume                  48
_journal_year                    2009
_chemical_formula_moiety         'C9 H18 Cu N9 O4 +, N O3 -, 0.5 H2 O'
_chemical_formula_sum            'C9 H19 Cu N10 O7.5'
_chemical_formula_weight         450.88
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                115.481(2)
_cell_angle_beta                 108.755(2)
_cell_angle_gamma                95.182(2)
_cell_formula_units_Z            2
_cell_length_a                   8.7250(5)
_cell_length_b                   10.4360(6)
_cell_length_c                   11.2345(6)
_cell_measurement_reflns_used    6426
_cell_measurement_temperature    423(2)
_cell_measurement_theta_max      28.70
_cell_measurement_theta_min      2.19
_cell_volume                     842.55(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      423(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_device_type  'Bruker SMART 1K CCD diffractometer'
_diffrn_measurement_method       'thin-slice ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7504
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.70
_diffrn_reflns_theta_min         2.19
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.361
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            blue-green
_exptl_crystal_density_diffrn    1.777
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3912
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0290
_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)+(0.0247P)²+1.0205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0717
_reflns_number_gt                3562
_reflns_number_total             3912
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic9013448_si_001_4.cif
_cod_data_source_block           ah85_compound_3
_cod_original_cell_volume        842.55(8)
_cod_original_formula_sum        'C9 H19 Cu N10 O7.50'
_cod_database_code               4303485
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 0.45226(3) 0.74817(3) 0.71892(2) 0.01279(7) Uani 1 1 d . . .
N1 N 0.8388(2) 0.58594(18) 0.91252(18) 0.0167(3) Uani 1 1 d . . .
C2 C 0.6958(2) 0.6250(2) 0.8704(2) 0.0146(4) Uani 1 1 d . . .
N2 N 0.5622(2) 0.5566(2) 0.8762(2) 0.0197(3) Uani 1 1 d D . .
H2A H 0.472(2) 0.573(3) 0.844(3) 0.022(6) Uiso 1 1 d D . .
H2B H 0.562(3) 0.479(2) 0.878(3) 0.026(7) Uiso 1 1 d D . .
N3 N 0.67670(19) 0.72691(17) 0.82483(17) 0.0136(3) Uani 1 1 d . . .
C4 C 0.8227(2) 0.7939(2) 0.83244(19) 0.0126(3) Uani 1 1 d . . .
C5 C 0.9740(2) 0.7605(2) 0.8712(2) 0.0151(4) Uani 1 1 d . . .
C6 C 0.9796(2) 0.6491(2) 0.9111(2) 0.0171(4) Uani 1 1 d . . .
N6 N 1.1183(2) 0.6080(2) 0.9509(2) 0.0266(4) Uani 1 1 d D . .
H6A H 1.200(3) 0.651(3) 0.950(3) 0.033(8) Uiso 1 1 d D . .
H6B H 1.120(3) 0.548(2) 0.981(3) 0.026(7) Uiso 1 1 d D . .
N7 N 1.0976(2) 0.85407(18) 0.87092(17) 0.0165(3) Uani 1 1 d . . .
C8 C 1.0195(2) 0.9405(2) 0.8322(2) 0.0155(4) Uani 1 1 d . . .
H8 H 1.0718 1.0148 0.8223 0.019 Uiso 1 1 calc R . .
N9 N 0.85269(19) 0.90971(17) 0.80784(17) 0.0132(3) Uani 1 1 d . . .
C10 C 0.7340(2) 0.9888(2) 0.7674(2) 0.0171(4) Uani 1 1 d . . .
H10A H 0.7961 1.0836 0.7893 0.020 Uiso 1 1 calc R . .
H10B H 0.6674 1.0067 0.8246 0.020 Uiso 1 1 calc R . .
C11 C 0.6171(2) 0.9047(2) 0.6087(2) 0.0185(4) Uani 1 1 d . . .
H11A H 0.5383 0.9600 0.5885 0.022 Uiso 1 1 calc R . .
H11B H 0.6824 0.8952 0.5513 0.022 Uiso 1 1 calc R . .
N12 N 0.5229(2) 0.75642(18) 0.56705(17) 0.0155(3) Uani 1 1 d D . .
H12 H 0.581(3) 0.701(2) 0.545(3) 0.022(6) Uiso 1 1 d D . .
C13 C 0.3649(3) 0.6963(2) 0.4354(2) 0.0216(4) Uani 1 1 d . . .
H13A H 0.3254 0.5906 0.3950 0.026 Uiso 1 1 calc R . .
H13B H 0.3853 0.7151 0.3637 0.026 Uiso 1 1 calc R . .
C14 C 0.2331(3) 0.7700(3) 0.4753(2) 0.0236(4) Uani 1 1 d . . .
H14A H 0.2555 0.8686 0.4875 0.028 Uiso 1 1 calc R . .
H14B H 0.1226 0.7142 0.3991 0.028 Uiso 1 1 calc R . .
N15 N 0.2382(2) 0.7770(2) 0.61132(19) 0.0193(3) Uani 1 1 d D . .
H15A H 0.159(3) 0.714(2) 0.595(3) 0.027(7) Uiso 1 1 d D . .
H15B H 0.232(4) 0.858(2) 0.666(3) 0.036(8) Uiso 1 1 d D . .
N16 N 0.2023(2) 0.43376(19) 0.56236(19) 0.0219(4) Uani 1 1 d . . .
O1 O 0.34525(18) 0.49743(16) 0.57999(17) 0.0236(3) Uani 1 1 d . . .
O2 O 0.1314(3) 0.5030(2) 0.6394(3) 0.0557(6) Uani 1 1 d . . .
O3 O 0.1372(2) 0.30352(18) 0.46867(18) 0.0323(4) Uani 1 1 d . . .
O4 O 0.3991(2) 0.80507(19) 0.88944(18) 0.0233(3) Uani 1 1 d . . .
H4A H 0.320(5) 0.828(4) 0.889(4) 0.048(10) Uiso 1 1 d . . .
H4B H 0.463(4) 0.835(3) 0.964(3) 0.034(8) Uiso 1 1 d . . .
N17 N 0.3940(3) 0.1837(2) -0.2022(2) 0.0305(4) Uani 1 1 d . . .
O5 O 0.3584(2) 0.09650(18) -0.15879(18) 0.0309(4) Uani 1 1 d . . .
O6 O 0.5395(2) 0.25333(19) -0.1567(2) 0.0341(4) Uani 1 1 d . . .
O7 O 0.2827(4) 0.1993(4) -0.2913(4) 0.1050(13) Uani 1 1 d . . .
O8 O 0.9773(6) 1.0093(5) 0.5786(6) 0.0635(13) Uani 0.50 1 d P . .
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
N3 Cu N12 92.98(6) . . ?
N3 Cu N15 176.49(7) . . ?
N3 Cu O1 91.61(6) . . ?
N3 Cu O4 90.36(7) . . ?
N12 Cu N15 84.11(7) . . ?
N12 Cu O1 90.62(6) . . ?
N12 Cu O4 162.60(7) . . ?
N15 Cu O1 90.40(7) . . ?
N15 Cu O4 91.85(7) . . ?
O1 Cu O4 106.36(7) . . ?
C2 N1 C6 119.96(16) . . ?
N1 C2 N2 115.62(17) . . ?
N1 C2 N3 126.03(17) . . ?
N2 C2 N3 118.34(16) . . ?
Cu N3 C2 124.55(12) . . ?
Cu N3 C4 121.92(12) . . ?
C2 N3 C4 112.37(15) . . ?
N3 C4 C5 126.07(17) . . ?
N3 C4 N9 127.98(16) . . ?
C5 C4 N9 105.93(16) . . ?
C4 C5 C6 117.30(17) . . ?
C4 C5 N7 110.39(16) . . ?
C6 C5 N7 132.18(17) . . ?
N1 C6 C5 118.11(17) . . ?
N1 C6 N6 119.21(18) . . ?
C5 C6 N6 122.65(18) . . ?
C5 N7 C8 104.36(15) . . ?
N7 C8 N9 112.97(17) . . ?
C4 N9 C8 106.36(15) . . ?
C4 N9 C10 127.69(15) . . ?
C8 N9 C10 125.94(16) . . ?
N9 C10 C11 112.66(16) . . ?
C10 C11 N12 111.74(15) . . ?
Cu N12 C11 114.17(12) . . ?
Cu N12 C13 105.33(12) . . ?
C11 N12 C13 112.62(15) . . ?
N12 C13 C14 108.88(16) . . ?
C13 C14 N15 108.99(16) . . ?
Cu N15 C14 112.20(13) . . ?
O1 N16 O2 119.68(18) . . ?
O1 N16 O3 118.88(17) . . ?
O2 N16 O3 121.44(19) . . ?
Cu O1 N16 121.13(12) . . ?
O5 N17 O6 120.49(19) . . ?
O5 N17 O7 120.3(2) . . ?
O6 N17 O7 119.2(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 N3 2.0266(15) . ?
Cu N12 2.0227(16) . ?
Cu N15 2.0004(17) . ?
Cu O1 2.2940(15) . ?
Cu O4 1.9699(16) . ?
N1 C2 1.351(2) . ?
N1 C6 1.348(3) . ?
C2 N2 1.346(2) . ?
C2 N3 1.366(2) . ?
N3 C4 1.355(2) . ?
C4 C5 1.378(2) . ?
C4 N9 1.372(2) . ?
C5 C6 1.414(3) . ?
C5 N7 1.390(2) . ?
C6 N6 1.326(2) . ?
N7 C8 1.314(2) . ?
C8 N9 1.371(2) . ?
N9 C10 1.461(2) . ?
C10 C11 1.521(3) . ?
C11 N12 1.480(3) . ?
N12 C13 1.489(2) . ?
C13 C14 1.519(3) . ?
C14 N15 1.484(3) . ?
N16 O1 1.271(2) . ?
N16 O2 1.241(2) . ?
N16 O3 1.234(2) . ?
N17 O5 1.261(2) . ?
N17 O6 1.224(3) . ?
N17 O7 1.231(3) . ?
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
N2 H2A O4 0.817(15) 2.44(2) 3.040(2) 131(2) .
N2 H2A O1 0.817(15) 2.53(2) 3.002(2) 118(2) .
N2 H2B O6 0.813(16) 2.198(16) 3.004(2) 171(3) 1_556
N6 H6A O6 0.811(16) 2.40(3) 2.873(3) 119(2) 2_766
N6 H6B N1 0.827(16) 2.186(16) 3.005(2) 171(3) 2_767
N12 H12 O1 0.812(15) 2.236(17) 3.013(2) 160(2) 2_666
N12 H12 O3 0.812(15) 2.52(2) 3.198(2) 142(2) 2_666
N15 H15A O3 0.817(16) 2.42(2) 3.034(2) 133(2) 2_566
N15 H15A O2 0.817(16) 2.47(2) 3.103(3) 135(2) .
N15 H15B O5 0.821(16) 2.28(2) 3.017(3) 150(3) 1_566
O4 H4A N7 0.75(4) 1.94(4) 2.684(2) 171(4) 1_455
O4 H4B O5 0.75(3) 2.00(3) 2.740(2) 176(3) 2_666
O4 H4B N17 0.75(3) 2.66(3) 3.339(3) 152(3) 2_666
