#------------------------------------------------------------------------------
#$Date: 2019-12-17 12:00:47 +0200 (Tue, 17 Dec 2019) $
#$Revision: 245255 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/66/1556618.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_1556618
loop_
_publ_author_name
'Strassl, F.'
'Hoffmann, A.'
'Grimm-Lebsanft, B.'
'Rukser, D.'
'Biebl, F.'
'Tran, M.A.'
'Metz, F.'
'Rubhausen, M.'
'Herres-Pawlis, S.'
_publ_section_title
;
 Fluorescent Bis(guanidine) Copper Complexes as Precursors for
 Hydroxylation Catalysis
;
_journal_name_full               Inorganics
_journal_page_first              114
_journal_paper_doi               10.3390/inorganics6040114
_journal_volume                  6
_journal_year                    2018
_chemical_formula_moiety         'C17 H26 Br Cu N6'
_chemical_formula_sum            'C17 H26 Br Cu N6'
_chemical_formula_weight         457.89
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 93.439(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1936(10)
_cell_length_b                   12.8127(17)
_cell_length_c                   20.599(3)
_cell_measurement_reflns_used    2690
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.55
_cell_measurement_theta_min      2.54
_cell_volume                     1895.2(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'multi layer optics'
_diffrn_radiation_source         microsource
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_av_sigmaI/netI    0.0597
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            25339
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    3.273
_exptl_absorpt_correction_T_max  0.4401
_exptl_absorpt_correction_T_min  0.3543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.912
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4516
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0360
_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)+(0.0188P)²+2.7485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0900
_reflns_number_gt                3822
_reflns_number_total             4516
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C2.cif
_cod_data_source_block           a17_a25
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1895.2(4)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1556618
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
Br1 Br 0.09443(4) 0.73594(2) 0.044173(14) 0.01479(9) Uani 1 1 d . . .
Cu1 Cu 0.21286(4) 0.78683(3) -0.053608(16) 0.01092(10) Uani 1 1 d . . .
N1 N 0.3103(3) 1.05710(18) -0.02528(12) 0.0124(5) Uani 1 1 d . . .
C1 C 0.3753(4) 1.1646(2) -0.02351(15) 0.0170(6) Uani 1 1 d . . .
H1A H 0.4950 1.1711 0.0026 0.020 Uiso 1 1 calc R . .
H1B H 0.2825 1.2115 -0.0052 0.020 Uiso 1 1 calc R . .
N2 N 0.3079(3) 1.10192(19) -0.12969(12) 0.0145(5) Uani 1 1 d . . .
C2 C 0.3993(4) 1.1893(3) -0.09451(16) 0.0209(7) Uani 1 1 d . . .
H2A H 0.3388 1.2564 -0.1070 0.025 Uiso 1 1 calc R . .
H2B H 0.5329 1.1932 -0.1034 0.025 Uiso 1 1 calc R . .
N3 N 0.2002(3) 0.93077(18) -0.10061(11) 0.0105(5) Uani 1 1 d . . .
C3 C 0.2347(4) 1.0155(2) 0.03306(14) 0.0145(6) Uani 1 1 d . . .
H3A H 0.1895 0.9443 0.0247 0.022 Uiso 1 1 calc R . .
H3B H 0.1313 1.0596 0.0455 0.022 Uiso 1 1 calc R . .
H3C H 0.3321 1.0145 0.0684 0.022 Uiso 1 1 calc R . .
N4 N 0.3523(3) 0.71350(18) -0.12294(11) 0.0116(5) Uani 1 1 d . . .
C4 C 0.2664(4) 1.0242(2) -0.08684(13) 0.0099(5) Uani 1 1 d . . .
N5 N 0.4191(3) 0.54837(18) -0.07765(12) 0.0123(5) Uani 1 1 d . . .
C5 C 0.3676(5) 1.0848(3) -0.19525(15) 0.0242(7) Uani 1 1 d . . .
H5A H 0.2814 1.0365 -0.2184 0.036 Uiso 1 1 calc R . .
H5B H 0.4933 1.0549 -0.1928 0.036 Uiso 1 1 calc R . .
H5C H 0.3684 1.1514 -0.2186 0.036 Uiso 1 1 calc R . .
N6 N 0.6347(3) 0.61769(19) -0.14026(12) 0.0125(5) Uani 1 1 d . . .
C6 C 0.1196(4) 0.9095(2) -0.16401(13) 0.0110(5) Uani 1 1 d . . .
C7 C -0.0432(4) 0.9602(2) -0.18762(14) 0.0153(6) Uani 1 1 d . . .
H7 H -0.0982 1.0122 -0.1621 0.018 Uiso 1 1 calc R . .
C8 C -0.1242(4) 0.9344(3) -0.24836(14) 0.0191(6) Uani 1 1 d . . .
H8 H -0.2337 0.9696 -0.2644 0.023 Uiso 1 1 calc R . .
C9 C -0.0468(4) 0.8576(3) -0.28590(14) 0.0193(7) Uani 1 1 d . . .
H9 H -0.1034 0.8398 -0.3273 0.023 Uiso 1 1 calc R . .
C10 C 0.1143(4) 0.8071(2) -0.26233(14) 0.0157(6) Uani 1 1 d . . .
H10 H 0.1669 0.7542 -0.2878 0.019 Uiso 1 1 calc R . .
C11 C 0.2002(4) 0.8328(2) -0.20186(13) 0.0113(5) Uani 1 1 d . . .
C12 C 0.3823(4) 0.7844(2) -0.17796(14) 0.0131(6) Uani 1 1 d . . .
H12A H 0.4358 0.7448 -0.2137 0.016 Uiso 1 1 calc R . .
H12B H 0.4716 0.8398 -0.1638 0.016 Uiso 1 1 calc R . .
C13 C 0.4638(4) 0.6341(2) -0.11401(13) 0.0094(5) Uani 1 1 d . . .
C14 C 0.2240(4) 0.5234(2) -0.07051(15) 0.0152(6) Uani 1 1 d . . .
H14A H 0.2145 0.4548 -0.0498 0.023 Uiso 1 1 calc R . .
H14B H 0.1576 0.5220 -0.1135 0.023 Uiso 1 1 calc R . .
H14C H 0.1684 0.5765 -0.0434 0.023 Uiso 1 1 calc R . .
C15 C 0.7736(4) 0.7007(2) -0.14355(15) 0.0175(6) Uani 1 1 d . . .
H15A H 0.8806 0.6748 -0.1661 0.026 Uiso 1 1 calc R . .
H15B H 0.8149 0.7225 -0.0994 0.026 Uiso 1 1 calc R . .
H15C H 0.7184 0.7604 -0.1673 0.026 Uiso 1 1 calc R . .
C16 C 0.7123(4) 0.5191(2) -0.11367(15) 0.0171(6) Uani 1 1 d . . .
H16A H 0.7999 0.5317 -0.0756 0.020 Uiso 1 1 calc R . .
H16B H 0.7773 0.4798 -0.1469 0.020 Uiso 1 1 calc R . .
C17 C 0.5406(4) 0.4618(2) -0.09436(16) 0.0182(6) Uani 1 1 d . . .
H17A H 0.4843 0.4201 -0.1309 0.022 Uiso 1 1 calc R . .
H17B H 0.5688 0.4155 -0.0566 0.022 Uiso 1 1 calc 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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
N4 Cu1 N3 95.32(9) . .
N4 Cu1 Br1 134.67(7) . .
N3 Cu1 Br1 129.99(7) . .
C4 N1 C3 125.7(2) . .
C4 N1 C1 112.0(2) . .
C3 N1 C1 117.6(2) . .
N1 C1 C2 103.2(2) . .
N1 C1 H1A 111.1 . .
C2 C1 H1A 111.1 . .
N1 C1 H1B 111.1 . .
C2 C1 H1B 111.1 . .
H1A C1 H1B 109.1 . .
C4 N2 C5 124.9(3) . .
C4 N2 C2 110.1(2) . .
C5 N2 C2 115.1(2) . .
N2 C2 C1 104.1(2) . .
N2 C2 H2A 110.9 . .
C1 C2 H2A 110.9 . .
N2 C2 H2B 110.9 . .
C1 C2 H2B 110.9 . .
H2A C2 H2B 109.0 . .
C4 N3 C6 119.7(2) . .
C4 N3 Cu1 134.58(19) . .
C6 N3 Cu1 105.13(17) . .
N1 C3 H3A 109.5 . .
N1 C3 H3B 109.5 . .
H3A C3 H3B 109.5 . .
N1 C3 H3C 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
C13 N4 C12 118.1(2) . .
C13 N4 Cu1 126.17(19) . .
C12 N4 Cu1 110.93(17) . .
N3 C4 N1 123.1(3) . .
N3 C4 N2 127.7(3) . .
N1 C4 N2 109.1(2) . .
C13 N5 C14 119.2(2) . .
C13 N5 C17 108.3(2) . .
C14 N5 C17 116.7(2) . .
N2 C5 H5A 109.5 . .
N2 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
N2 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C13 N6 C15 122.0(2) . .
C13 N6 C16 108.0(2) . .
C15 N6 C16 113.3(2) . .
C7 C6 C11 119.8(3) . .
C7 C6 N3 121.1(3) . .
C11 C6 N3 119.0(2) . .
C8 C7 C6 120.0(3) . .
C8 C7 H7 120.0 . .
C6 C7 H7 120.0 . .
C9 C8 C7 120.7(3) . .
C9 C8 H8 119.7 . .
C7 C8 H8 119.7 . .
C8 C9 C10 119.3(3) . .
C8 C9 H9 120.4 . .
C10 C9 H9 120.4 . .
C9 C10 C11 121.2(3) . .
C9 C10 H10 119.4 . .
C11 C10 H10 119.4 . .
C10 C11 C6 119.1(3) . .
C10 C11 C12 121.6(3) . .
C6 C11 C12 119.2(2) . .
N4 C12 C11 109.8(2) . .
N4 C12 H12A 109.7 . .
C11 C12 H12A 109.7 . .
N4 C12 H12B 109.7 . .
C11 C12 H12B 109.7 . .
H12A C12 H12B 108.2 . .
N4 C13 N5 122.5(2) . .
N4 C13 N6 128.0(3) . .
N5 C13 N6 109.3(2) . .
N5 C14 H14A 109.5 . .
N5 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
N5 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
N6 C15 H15A 109.5 . .
N6 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
N6 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
N6 C16 C17 102.5(2) . .
N6 C16 H16A 111.3 . .
C17 C16 H16A 111.3 . .
N6 C16 H16B 111.3 . .
C17 C16 H16B 111.3 . .
H16A C16 H16B 109.2 . .
N5 C17 C16 101.7(2) . .
N5 C17 H17A 111.4 . .
C16 C17 H17A 111.4 . .
N5 C17 H17B 111.4 . .
C16 C17 H17B 111.4 . .
H17A C17 H17B 109.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 Cu1 2.3267(5) .
Cu1 N4 2.025(2) .
Cu1 N3 2.082(2) .
N1 C4 1.356(4) .
N1 C3 1.450(4) .
N1 C1 1.455(4) .
C1 C2 1.516(4) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
N2 C4 1.375(4) .
N2 C5 1.458(4) .
N2 C2 1.468(4) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
N3 C4 1.313(4) .
N3 C6 1.423(3) .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 0.9800 .
N4 C13 1.301(4) .
N4 C12 1.478(4) .
N5 C13 1.379(4) .
N5 C14 1.456(3) .
N5 C17 1.466(4) .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
N6 C13 1.389(3) .
N6 C15 1.464(4) .
N6 C16 1.474(4) .
C6 C7 1.400(4) .
C6 C11 1.402(4) .
C7 C8 1.388(4) .
C7 H7 0.9500 .
C8 C9 1.388(5) .
C8 H8 0.9500 .
C9 C10 1.389(4) .
C9 H9 0.9500 .
C10 C11 1.396(4) .
C10 H10 0.9500 .
C11 C12 1.506(4) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 C17 1.511(4) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
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
C4 N1 C1 C2 -9.8(3) . . . .
C3 N1 C1 C2 -166.9(2) . . . .
C4 N2 C2 C1 -10.6(3) . . . .
C5 N2 C2 C1 -158.2(3) . . . .
N1 C1 C2 N2 11.7(3) . . . .
N4 Cu1 N3 C4 -117.0(3) . . . .
Br1 Cu1 N3 C4 64.4(3) . . . .
N4 Cu1 N3 C6 53.76(18) . . . .
Br1 Cu1 N3 C6 -124.85(15) . . . .
N3 Cu1 N4 C13 152.4(2) . . . .
Br1 Cu1 N4 C13 -29.1(3) . . . .
N3 Cu1 N4 C12 -2.33(19) . . . .
Br1 Cu1 N4 C12 176.18(13) . . . .
C6 N3 C4 N1 166.2(2) . . . .
Cu1 N3 C4 N1 -24.1(4) . . . .
C6 N3 C4 N2 -15.9(4) . . . .
Cu1 N3 C4 N2 153.7(2) . . . .
C3 N1 C4 N3 -23.4(4) . . . .
C1 N1 C4 N3 -178.3(2) . . . .
C3 N1 C4 N2 158.4(2) . . . .
C1 N1 C4 N2 3.5(3) . . . .
C5 N2 C4 N3 -29.6(4) . . . .
C2 N2 C4 N3 -173.3(3) . . . .
C5 N2 C4 N1 148.5(3) . . . .
C2 N2 C4 N1 4.8(3) . . . .
C4 N3 C6 C7 -64.7(4) . . . .
Cu1 N3 C6 C7 122.9(2) . . . .
C4 N3 C6 C11 118.5(3) . . . .
Cu1 N3 C6 C11 -53.9(3) . . . .
C11 C6 C7 C8 0.0(4) . . . .
N3 C6 C7 C8 -176.9(3) . . . .
C6 C7 C8 C9 0.8(5) . . . .
C7 C8 C9 C10 -0.6(5) . . . .
C8 C9 C10 C11 -0.5(5) . . . .
C9 C10 C11 C6 1.3(4) . . . .
C9 C10 C11 C12 -175.4(3) . . . .
C7 C6 C11 C10 -1.0(4) . . . .
N3 C6 C11 C10 175.9(3) . . . .
C7 C6 C11 C12 175.7(3) . . . .
N3 C6 C11 C12 -7.4(4) . . . .
C13 N4 C12 C11 150.9(2) . . . .
Cu1 N4 C12 C11 -52.1(3) . . . .
C10 C11 C12 N4 -110.8(3) . . . .
C6 C11 C12 N4 72.6(3) . . . .
C12 N4 C13 N5 -160.8(2) . . . .
Cu1 N4 C13 N5 46.1(4) . . . .
C12 N4 C13 N6 15.6(4) . . . .
Cu1 N4 C13 N6 -137.5(2) . . . .
C14 N5 C13 N4 25.2(4) . . . .
C17 N5 C13 N4 161.8(3) . . . .
C14 N5 C13 N6 -151.8(2) . . . .
C17 N5 C13 N6 -15.2(3) . . . .
C15 N6 C13 N4 43.4(4) . . . .
C16 N6 C13 N4 177.5(3) . . . .
C15 N6 C13 N5 -139.8(3) . . . .
C16 N6 C13 N5 -5.7(3) . . . .
C13 N6 C16 C17 23.2(3) . . . .
C15 N6 C16 C17 161.6(2) . . . .
C13 N5 C17 C16 28.8(3) . . . .
C14 N5 C17 C16 166.6(2) . . . .
N6 C16 C17 N5 -30.5(3) . . . .
