#------------------------------------------------------------------------------
#$Date: 2019-11-23 09:24:09 +0200 (Sat, 23 Nov 2019) $
#$Revision: 232711 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/80/4348058.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_4348058
loop_
_publ_author_name
'Mandal, Soham'
'Wang, Can'
'Prajapati, Rajneesh K.'
'Kösters, Jutta'
'Verma, Sandeep'
'Chi, Lifeng'
'Müller, Jens'
_publ_section_title
;
 Metal-Mediated Assembly of 1,N(6)-Ethenoadenine: From Surfaces to DNA
 Duplexes.
;
_journal_issue                   14
_journal_name_full               'Inorganic chemistry'
_journal_page_first              7041
_journal_page_last               7050
_journal_paper_doi               10.1021/acs.inorgchem.6b00927
_journal_volume                  55
_journal_year                    2016
_chemical_formula_sum            'C20 H28 Cu2 N12 O14'
_chemical_formula_weight         787.62
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                104.1619(12)
_cell_angle_beta                 103.0423(13)
_cell_angle_gamma                99.0491(12)
_cell_formula_units_Z            1
_cell_length_a                   7.3996(3)
_cell_length_b                   8.9100(4)
_cell_length_c                   11.8127(5)
_cell_measurement_reflns_used    8265
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.073
_cell_measurement_theta_min      2.42
_cell_volume                     716.81(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Photon 100 CMOS-detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9821
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.272
_diffrn_reflns_theta_min         2.583
_diffrn_source                   Microfocus
_exptl_absorpt_coefficient_mu    1.576
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.825
_exptl_crystal_description       block
_exptl_crystal_F_000             402
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0446P)²+0.3652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0801
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3154
_reflns_number_total             3494
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic6b00927_si_002.cif
_cod_data_source_block           sadp-1
_cod_database_code               4348058
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.846
_shelx_estimated_absorpt_t_max   0.925
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Cu1 Cu 0.52471(3) 0.53281(2) 0.64090(2) 0.01842(8) Uani 1 1 d . .
N1 N 0.2992(2) 0.93104(18) 0.62944(15) 0.0208(3) Uani 1 1 d . .
C2 C 0.2303(3) 1.0336(2) 0.56987(17) 0.0222(4) Uani 1 1 d . .
H2 H 0.1951 1.1228 0.6149 0.027 Uiso 1 1 calc R U
N3 N 0.2113(2) 1.01446(18) 0.45587(15) 0.0221(3) Uani 1 1 d . .
C4 C 0.2679(3) 0.8850(2) 0.39966(17) 0.0201(4) Uani 1 1 d . .
C5 C 0.6567(2) 0.2245(2) 0.55069(16) 0.0186(3) Uani 1 1 d . .
N6 N 0.4126(2) 0.72156(19) 0.65535(14) 0.0211(3) Uani 1 1 d . .
C6 C 0.3579(2) 0.7969(2) 0.57417(17) 0.0188(3) Uani 1 1 d . .
N7 N 0.6206(2) 0.33628(18) 0.64174(14) 0.0202(3) Uani 1 1 d . .
C8 C 0.6750(3) 0.2934(2) 0.74162(17) 0.0223(4) Uani 1 1 d . .
H8 H 0.6668 0.3504 0.8189 0.027 Uiso 1 1 calc R U
N9 N 0.2569(2) 0.83938(18) 0.27804(15) 0.0212(3) Uani 1 1 d . .
C91 C 0.1743(3) 0.9197(2) 0.19032(19) 0.0286(4) Uani 1 1 d . .
H91A H 0.2423 1.0328 0.2178 0.034 Uiso 1 1 calc R U
H91B H 0.0391 0.9158 0.1884 0.034 Uiso 1 1 calc R U
C92 C 0.1864(4) 0.8446(3) 0.0637(2) 0.0403(6) Uani 1 1 d . .
H92C H 0.3192 0.8432 0.0659 0.060 Uiso 1 1 calc R U
H92A H 0.1384 0.9063 0.0101 0.060 Uiso 1 1 calc R U
H92B H 0.1093 0.7355 0.0332 0.060 Uiso 1 1 calc R U
C10 C 0.3882(3) 0.8077(2) 0.76361(18) 0.0247(4) Uani 1 1 d . .
H10 H 0.4156 0.7799 0.8374 0.030 Uiso 1 1 calc R U
C11 C 0.3204(3) 0.9357(2) 0.75019(18) 0.0252(4) Uani 1 1 d . .
H11 H 0.2927 1.0134 0.8108 0.030 Uiso 1 1 calc R U
C1F C 0.1505(3) 0.3574(2) 0.48447(17) 0.0211(4) Uani 1 1 d . .
O1F O 0.32356(18) 0.41701(15) 0.49155(12) 0.0207(3) Uani 1 1 d . .
O2F O 0.0836(2) 0.35502(19) 0.56888(14) 0.0311(3) Uani 1 1 d . .
O1W O 0.7374(2) 0.65565(17) 0.78569(14) 0.0247(3) Uani 1 1 d . .
H1W H 0.831(4) 0.630(3) 0.791(3) 0.038(8) Uiso 1 1 d . .
H2W H 0.726(4) 0.672(3) 0.846(3) 0.037(8) Uiso 1 1 d . .
O2W O 0.0510(3) 0.5482(2) 0.78528(18) 0.0372(4) Uani 1 1 d . .
H3W H 0.065(4) 0.496(3) 0.725(3) 0.040(8) Uiso 1 1 d . .
H4W H 0.120(5) 0.538(4) 0.839(3) 0.046(9) Uiso 1 1 d . .
N2N N 0.7004(3) 0.6591(2) 0.06529(16) 0.0342(4) Uani 1 1 d . .
O21 O 0.7393(3) 0.5321(2) 0.01531(15) 0.0473(5) Uani 1 1 d . .
O22 O 0.6749(3) 0.7587(2) 0.00666(15) 0.0415(4) Uani 1 1 d . .
O23 O 0.6895(3) 0.6883(2) 0.17085(15) 0.0473(5) Uani 1 1 d . .
H1F H 0.073(3) 0.310(3) 0.405(2) 0.022(5) Uiso 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'
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
O1F Cu1 N6 90.68(6) . .
O1F Cu1 O1W 176.36(6) . .
N6 Cu1 O1W 89.07(6) . .
O1F Cu1 N7 90.43(6) . .
N6 Cu1 N7 172.63(6) . .
O1W Cu1 N7 90.28(6) . .
O1F Cu1 O1F 81.57(5) . 2_666
N6 Cu1 O1F 95.21(6) . 2_666
O1W Cu1 O1F 94.83(6) . 2_666
N7 Cu1 O1F 92.16(6) . 2_666
C2 N1 C11 128.46(16) . .
C2 N1 C6 124.16(17) . .
C11 N1 C6 107.37(16) . .
N3 C2 N1 123.02(17) . .
N3 C2 H2 118.5 . .
N1 C2 H2 118.5 . .
C2 N3 C4 114.15(17) . .
N3 C4 N9 124.30(17) . .
N3 C4 C5 128.51(18) . 2_666
N9 C4 C5 107.20(16) . 2_666
N7 C5 C4 108.45(16) . 2_666
N7 C5 C6 135.29(17) . 2_666
C4 C5 C6 116.18(16) 2_666 2_666
C6 N6 C10 106.51(16) . .
C6 N6 Cu1 130.35(13) . .
C10 N6 Cu1 123.02(13) . .
N6 C6 N1 109.30(16) . .
N6 C6 C5 136.77(17) . 2_666
N1 C6 C5 113.94(16) . 2_666
C8 N7 C5 105.48(15) . .
C8 N7 Cu1 122.98(12) . .
C5 N7 Cu1 131.43(13) . .
N7 C8 N9 112.84(16) . 2_666
N7 C8 H8 123.6 . .
N9 C8 H8 123.6 2_666 .
C8 N9 C4 106.02(16) 2_666 .
C8 N9 C91 129.32(17) 2_666 .
C4 N9 C91 124.55(16) . .
N9 C91 C92 112.37(17) . .
N9 C91 H91A 109.1 . .
C92 C91 H91A 109.1 . .
N9 C91 H91B 109.1 . .
C92 C91 H91B 109.1 . .
H91A C91 H91B 107.9 . .
C91 C92 H92C 109.5 . .
C91 C92 H92A 109.5 . .
H92C C92 H92A 109.5 . .
C91 C92 H92B 109.5 . .
H92C C92 H92B 109.5 . .
H92A C92 H92B 109.5 . .
C11 C10 N6 110.94(18) . .
C11 C10 H10 124.5 . .
N6 C10 H10 124.5 . .
C10 C11 N1 105.88(16) . .
C10 C11 H11 127.1 . .
N1 C11 H11 127.1 . .
O2F C1F O1F 126.46(18) . .
O2F C1F H1F 119.7(14) . .
O1F C1F H1F 113.8(14) . .
C1F O1F Cu1 126.14(12) . .
C1F O1F Cu1 134.47(12) . 2_666
Cu1 O1F Cu1 98.43(5) . 2_666
Cu1 O1W H1W 117(2) . .
Cu1 O1W H2W 122(2) . .
H1W O1W H2W 105(3) . .
H3W O2W H4W 109(3) . .
O23 N2N O21 120.8(2) . .
O23 N2N O22 120.20(18) . .
O21 N2N O22 119.04(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1F 1.9580(13) .
Cu1 N6 1.9769(15) .
Cu1 O1W 1.9818(15) .
Cu1 N7 1.9913(16) .
Cu1 O1F 2.2103(13) 2_666
N1 C2 1.375(2) .
N1 C11 1.389(3) .
N1 C6 1.398(2) .
C2 N3 1.287(3) .
C2 H2 0.9500 .
N3 C4 1.360(2) .
C4 N9 1.374(2) .
C4 C5 1.382(3) 2_666
C5 N7 1.382(2) .
C5 C4 1.382(3) 2_666
C5 C6 1.417(3) 2_666
N6 C6 1.326(2) .
N6 C10 1.387(2) .
C6 C5 1.417(3) 2_666
N7 C8 1.324(2) .
C8 N9 1.347(2) 2_666
C8 H8 0.9500 .
N9 C8 1.347(2) 2_666
N9 C91 1.475(2) .
C91 C92 1.510(3) .
C91 H91A 0.9900 .
C91 H91B 0.9900 .
C92 H92C 0.9800 .
C92 H92A 0.9800 .
C92 H92B 0.9800 .
C10 C11 1.346(3) .
C10 H10 0.9500 .
C11 H11 0.9500 .
C1F O2F 1.212(2) .
C1F O1F 1.282(2) .
C1F H1F 0.94(2) .
O1F Cu1 2.2103(13) 2_666
O1W H1W 0.76(3) .
O1W H2W 0.71(3) .
O2W H3W 0.79(3) .
O2W H4W 0.75(3) .
N2N O23 1.234(2) .
N2N O21 1.250(2) .
N2N O22 1.264(3) .
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_4
C11 N1 C2 N3 -177.65(19) . .
C6 N1 C2 N3 0.8(3) . .
N1 C2 N3 C4 -0.9(3) . .
C2 N3 C4 N9 178.61(17) . .
C2 N3 C4 C5 -0.8(3) . 2_666
C10 N6 C6 N1 0.2(2) . .
Cu1 N6 C6 N1 -175.93(12) . .
C10 N6 C6 C5 -179.2(2) . 2_666
Cu1 N6 C6 C5 4.6(3) . 2_666
C2 N1 C6 N6 -178.66(17) . .
C11 N1 C6 N6 0.0(2) . .
C2 N1 C6 C5 0.9(3) . 2_666
C11 N1 C6 C5 179.64(16) . 2_666
C4 C5 N7 C8 0.5(2) 2_666 .
C6 C5 N7 C8 -176.2(2) 2_666 .
C4 C5 N7 Cu1 176.68(13) 2_666 .
C6 C5 N7 Cu1 0.0(3) 2_666 .
C5 N7 C8 N9 -0.4(2) . 2_666
Cu1 N7 C8 N9 -177.03(12) . 2_666
N3 C4 N9 C8 -179.62(17) . 2_666
C5 C4 N9 C8 -0.1(2) 2_666 2_666
N3 C4 N9 C91 -3.0(3) . .
C5 C4 N9 C91 176.51(18) 2_666 .
C8 N9 C91 C92 -5.5(3) 2_666 .
C4 N9 C91 C92 178.73(19) . .
C6 N6 C10 C11 -0.4(2) . .
Cu1 N6 C10 C11 176.07(14) . .
N6 C10 C11 N1 0.5(2) . .
C2 N1 C11 C10 178.33(18) . .
C6 N1 C11 C10 -0.3(2) . .
O2F C1F O1F Cu1 -4.1(3) . .
O2F C1F O1F Cu1 -170.28(14) . 2_666
