#------------------------------------------------------------------------------
#$Date: 2016-11-08 22:04:38 +0200 (Tue, 08 Nov 2016) $
#$Revision: 188225 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/07/7040784.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_7040784
loop_
_publ_author_name
'Krämer, Christoph'
'Leingang, Simone'
'Hübner, Olaf'
'Kaifer, Elisabeth'
'Wadepohl, Hubert'
'Himmel, Hans-Jörg'
_publ_section_title
;
 Construction of copper chains with new fluorescent
 guanidino-functionalized naphthyridine ligands.
;
_journal_issue                   42
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              16966
_journal_page_last               16983
_journal_paper_doi               10.1039/c6dt03166h
_journal_volume                  45
_journal_year                    2016
_chemical_formula_sum            'C25.6 H41.6 Cl12.8 N8'
_chemical_formula_weight         915.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-08-09 deposited with the CCDC.
2016-09-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 126.50(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.191(5)
_cell_length_b                   14.615(3)
_cell_length_c                   16.702(3)
_cell_measurement_reflns_used    6669
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.10
_cell_measurement_theta_min      2.18
_cell_volume                     4551(2)
_computing_cell_refinement       'DENZO/SKALEPACK (Bruker AXS, 1997-2009)'
_computing_data_collection       'COLLECT (Bruker AXS, 1997-2009)'
_computing_data_reduction        'DENZO/SKALEPACK (Bruker AXS, 1997-2009)'
_computing_molecular_graphics    'XPMA (Zsolnai, Huttner, 1994)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'NONIUS KAPPA CCD'
_diffrn_measurement_method       'O-Scan    '
_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  0.0601
_diffrn_reflns_av_unetI/netI     0.0738
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12732
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.102
_diffrn_reflns_theta_min         2.185
_exptl_absorpt_coefficient_mu    0.805
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       'box shaped'
_exptl_crystal_F_000             1875
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.931
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         6669
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0629
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1368P)²+1.9398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1906
_refine_ls_wR_factor_ref         0.2151
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4538
_reflns_number_total             6669
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6dt03166h2.cif
_cod_data_source_block           ck270n
_cod_depositor_comments
'Adding full bibliography for 7040782--7040791.cif.'
_cod_original_formula_sum        'C25.60 H41.60 Cl12.80 N8'
_cod_database_code               7040784
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.23330(3) 0.11137(4) 0.21450(4) 0.02863(17) Uani 1 1 d . . . . .
N1 N 0.34352(10) 0.04611(13) 0.73584(15) 0.0270(4) Uani 1 1 d . . . . .
H1N H 0.3059(17) 0.013(2) 0.722(2) 0.043(8) Uiso 1 1 d . . . . .
N2 N 0.28387(10) 0.17386(14) 0.73607(16) 0.0282(4) Uani 1 1 d . . . . .
H2N H 0.2844(14) 0.236(2) 0.752(2) 0.028(7) Uiso 1 1 d . . . . .
N3 N 0.39927(11) 0.18792(14) 0.77928(17) 0.0307(4) Uani 1 1 d . . . . .
H3N H 0.430(2) 0.154(3) 0.774(3) 0.070(12) Uiso 1 1 d . . . . .
N4 N 0.44910(10) 0.04085(12) 0.74691(15) 0.0252(4) Uani 1 1 d . . . . .
C1 C 0.39744(12) -0.00392(15) 0.74105(17) 0.0248(4) Uani 1 1 d . . . . .
C2 C 0.39180(13) -0.10035(15) 0.73838(19) 0.0292(5) Uani 1 1 d . . . . .
H2 H 0.3538 -0.1288 0.7331 0.035 Uiso 1 1 calc R U . . .
C3 C 0.44342(13) -0.15044(16) 0.74377(18) 0.0290(5) Uani 1 1 d . . . . .
H3 H 0.4415 -0.2140 0.7434 0.035 Uiso 1 1 calc R U . . .
C4 C 0.5000 -0.1058(2) 0.7500 0.0259(6) Uani 1 2 d S T P . .
C5 C 0.5000 -0.0094(2) 0.7500 0.0243(6) Uani 1 2 d S T P . .
C6 C 0.34211(12) 0.13786(15) 0.75026(17) 0.0258(4) Uani 1 1 d . . . . .
C7 C 0.21655(13) 0.12378(17) 0.6966(2) 0.0319(5) Uani 1 1 d . . . . .
H7 H 0.2286 0.0647 0.7308 0.038 Uiso 1 1 calc R U . . .
C8 C 0.17553(15) 0.10623(19) 0.5853(2) 0.0417(6) Uani 1 1 d . . . . .
H8A H 0.1601 0.1635 0.5502 0.062 Uiso 1 1 calc R U . . .
H8B H 0.1344 0.0687 0.5624 0.062 Uiso 1 1 calc R U . . .
H8C H 0.2062 0.0755 0.5731 0.062 Uiso 1 1 calc R U . . .
C9 C 0.17243(16) 0.1780(2) 0.7193(3) 0.0466(7) Uani 1 1 d . . . . .
H9A H 0.2004 0.1893 0.7897 0.070 Uiso 1 1 calc R U . . .
H9B H 0.1303 0.1438 0.6985 0.070 Uiso 1 1 calc R U . . .
H9C H 0.1586 0.2352 0.6843 0.070 Uiso 1 1 calc R U . . .
C10 C 0.40589(13) 0.28728(16) 0.7961(2) 0.0334(5) Uani 1 1 d . . . . .
H10 H 0.3820 0.3038 0.8266 0.040 Uiso 1 1 calc R U . . .
C11 C 0.48527(15) 0.3090(2) 0.8697(3) 0.0500(8) Uani 1 1 d . . . . .
H11A H 0.5042 0.2786 0.9318 0.075 Uiso 1 1 calc R U . . .
H11B H 0.4915 0.3738 0.8804 0.075 Uiso 1 1 calc R U . . .
H11C H 0.5102 0.2881 0.8434 0.075 Uiso 1 1 calc R U . . .
C12 C 0.37046(17) 0.33944(19) 0.6991(3) 0.0452(7) Uani 1 1 d . . . . .
H12A H 0.3941 0.3252 0.6692 0.068 Uiso 1 1 calc R U . . .
H12B H 0.3739 0.4040 0.7121 0.068 Uiso 1 1 calc R U . . .
H12C H 0.3209 0.3222 0.6546 0.068 Uiso 1 1 calc R U . . .
C21 C 0.3394(2) 0.0654(3) 0.4596(3) 0.0610(9) Uani 0.5 1 d . . P A 1
H21 H 0.3037 0.0778 0.3885 0.073 Uiso 0.5 1 calc R U P A 1
Cl2 Cl 0.3278(3) -0.0421(5) 0.4842(5) 0.095(2) Uani 0.5 1 d . . P A 1
Cl3 Cl 0.3366(4) 0.1477(4) 0.5239(5) 0.096(2) Uani 0.5 1 d . . P A 1
Cl4 Cl 0.4300(4) 0.0731(4) 0.4901(5) 0.0801(11) Uani 0.5 1 d . . P A 1
C22 C 0.3394(2) 0.0654(3) 0.4596(3) 0.0610(9) Uani 0.5 1 d . . P B 2
H22 H 0.3093 0.0825 0.3890 0.073 Uiso 0.5 1 calc R U P B 2
Cl5 Cl 0.2990(3) -0.0334(4) 0.4764(5) 0.0715(11) Uani 0.5 1 d . . P B 2
Cl6 Cl 0.33596(19) 0.1568(3) 0.5305(3) 0.0409(6) Uani 0.5 1 d . . P B 2
Cl7 Cl 0.4200(4) 0.0343(4) 0.4924(5) 0.105(2) Uani 0.5 1 d . . P B 2
C23 C 0.3639(5) 0.3381(6) 1.0271(5) 0.0478(18) Uani 0.4 1 d . . P C 1
H23 H 0.3421 0.3763 0.9675 0.057 Uiso 0.4 1 calc R U P C 1
Cl8 Cl 0.4237(2) 0.2592(4) 1.0308(4) 0.0547(11) Uani 0.4 1 d . . P C 1
Cl9 Cl 0.29408(10) 0.27442(12) 1.01956(14) 0.0462(4) Uani 0.4 1 d . . P C 1
Cl10 Cl 0.40758(19) 0.4076(2) 1.1308(2) 0.0672(9) Uani 0.4 1 d . . P C 1
C24 C 0.3969(4) 0.3659(5) 1.0292(5) 0.0323(13) Uani 0.4 1 d . . P D 2
H24 H 0.3613 0.3906 0.9625 0.039 Uiso 0.4 1 calc R U P D 2
Cl11 Cl 0.47910(10) 0.41806(16) 1.0767(2) 0.0688(7) Uani 0.4 1 d . . P D 2
Cl12 Cl 0.4000(2) 0.2467(3) 1.0189(4) 0.0477(9) Uani 0.4 1 d . . P D 2
Cl13 Cl 0.3688(2) 0.3922(2) 1.1041(3) 0.0752(9) Uani 0.4 1 d . . P D 2
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'
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
C6 N1 C1 127.84(19) . .
C6 N1 H1N 117(2) . .
C1 N1 H1N 115(2) . .
C6 N2 C7 125.0(2) . .
C6 N2 H2N 119.1(17) . .
C7 N2 H2N 115.9(17) . .
C6 N3 C10 125.61(19) . .
C6 N3 H3N 110(2) . .
C10 N3 H3N 123(2) . .
C1 N4 C5 117.6(2) . .
N4 C1 N1 118.9(2) . .
N4 C1 C2 124.1(2) . .
N1 C1 C2 117.04(19) . .
C3 C2 C1 118.3(2) . .
C3 C2 H2 120.9 . .
C1 C2 H2 120.9 . .
C2 C3 C4 119.9(2) . .
C2 C3 H3 120.0 . .
C4 C3 H3 120.0 . .
C5 C4 C3 117.53(14) . .
C5 C4 C3 117.53(14) . 2_656
C3 C4 C3 124.9(3) . 2_656
N4 C5 N4 114.9(3) . 2_656
N4 C5 C4 122.54(13) . .
N4 C5 C4 122.53(13) 2_656 .
N3 C6 N2 122.2(2) . .
N3 C6 N1 118.8(2) . .
N2 C6 N1 119.0(2) . .
N2 C7 C9 108.8(2) . .
N2 C7 C8 110.8(2) . .
C9 C7 C8 111.7(2) . .
N2 C7 H7 108.5 . .
C9 C7 H7 108.5 . .
C8 C7 H7 108.5 . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C7 C9 H9A 109.5 . .
C7 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C7 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
N3 C10 C12 111.3(2) . .
N3 C10 C11 107.4(2) . .
C12 C10 C11 112.7(2) . .
N3 C10 H10 108.4 . .
C12 C10 H10 108.4 . .
C11 C10 H10 108.4 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C10 C12 H12A 109.5 . .
C10 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C10 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
Cl3 C21 Cl2 116.8(4) . .
Cl3 C21 Cl4 104.9(4) . .
Cl2 C21 Cl4 108.0(3) . .
Cl3 C21 H21 109.0 . .
Cl2 C21 H21 109.0 . .
Cl4 C21 H21 109.0 . .
Cl7 C22 Cl6 117.5(3) . .
Cl7 C22 Cl5 108.1(3) . .
Cl6 C22 Cl5 104.8(3) . .
Cl7 C22 H22 108.7 . .
Cl6 C22 H22 108.7 . .
Cl5 C22 H22 108.7 . .
Cl10 C23 Cl8 111.5(5) . .
Cl10 C23 Cl9 109.9(5) . .
Cl8 C23 Cl9 108.5(5) . .
Cl10 C23 H23 109.0 . .
Cl8 C23 H23 109.0 . .
Cl9 C23 H23 109.0 . .
C23 Cl9 Cl9 164.9(3) . 7_557
Cl11 C24 Cl12 112.3(4) . .
Cl11 C24 Cl13 110.3(4) . .
Cl12 C24 Cl13 109.9(4) . .
Cl11 C24 H24 108.0 . .
Cl12 C24 H24 108.0 . .
Cl13 C24 H24 108.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C6 1.366(3) .
N1 C1 1.406(3) .
N1 H1N 0.90(3) .
N2 C6 1.333(3) .
N2 C7 1.478(3) .
N2 H2N 0.94(3) .
N3 C6 1.328(3) .
N3 C10 1.470(3) .
N3 H3N 0.92(4) .
N4 C1 1.317(3) .
N4 C5 1.365(2) .
C1 C2 1.414(3) .
C2 C3 1.360(3) .
C2 H2 0.9300 .
C3 C4 1.413(3) .
C3 H3 0.9300 .
C4 C5 1.409(4) .
C4 C3 1.413(3) 2_656
C5 N4 1.365(2) 2_656
C7 C9 1.510(4) .
C7 C8 1.524(4) .
C7 H7 0.9800 .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C10 C12 1.516(4) .
C10 C11 1.519(4) .
C10 H10 0.9800 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C21 Cl3 1.638(7) .
C21 Cl2 1.686(8) .
C21 Cl4 1.848(8) .
C21 H21 0.9800 .
C22 Cl7 1.668(9) .
C22 Cl6 1.817(6) .
C22 Cl5 1.831(7) .
C22 H22 0.9800 .
C23 Cl10 1.723(8) .
C23 Cl8 1.776(10) .
C23 Cl9 1.806(11) .
C23 H23 0.9800 .
Cl9 Cl9 1.878(4) 7_557
C24 Cl11 1.745(8) .
C24 Cl12 1.756(8) .
C24 Cl13 1.761(7) .
C24 H24 0.9800 .
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
C5 N4 C1 N1 -178.80(17) . .
C5 N4 C1 C2 0.4(3) . .
C6 N1 C1 N4 -10.3(4) . .
C6 N1 C1 C2 170.5(2) . .
N4 C1 C2 C3 1.1(4) . .
N1 C1 C2 C3 -179.7(2) . .
C1 C2 C3 C4 -1.1(4) . .
C2 C3 C4 C5 -0.2(3) . .
C2 C3 C4 C3 179.8(3) . 2_656
C1 N4 C5 N4 178.2(2) . 2_656
C1 N4 C5 C4 -1.8(2) . .
C3 C4 C5 N4 1.76(15) . .
C3 C4 C5 N4 -178.24(15) 2_656 .
C3 C4 C5 N4 -178.23(15) . 2_656
C3 C4 C5 N4 1.77(15) 2_656 2_656
C10 N3 C6 N2 -2.2(4) . .
C10 N3 C6 N1 178.7(2) . .
C7 N2 C6 N3 175.1(2) . .
C7 N2 C6 N1 -5.9(4) . .
C1 N1 C6 N3 -5.0(4) . .
C1 N1 C6 N2 175.9(2) . .
C6 N2 C7 C9 163.6(3) . .
C6 N2 C7 C8 -73.2(3) . .
C6 N3 C10 C12 -81.4(3) . .
C6 N3 C10 C11 154.8(3) . .
Cl10 C23 Cl9 Cl9 117.3(10) . 7_557
Cl8 C23 Cl9 Cl9 -120.5(11) . 7_557
