#------------------------------------------------------------------------------
#$Date: 2019-12-17 12:01:04 +0200 (Tue, 17 Dec 2019) $
#$Revision: 245257 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/66/1556620.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_1556620
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 Cl2 Cu N6'
_chemical_formula_sum            'C17 H26 Cl2 Cu N6'
_chemical_formula_weight         448.88
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 113.072(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.234(3)
_cell_length_b                   8.1012(14)
_cell_length_c                   17.631(3)
_cell_measurement_reflns_used    2191
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.05
_cell_measurement_theta_min      2.51
_cell_volume                     2001.9(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0838
_diffrn_reflns_av_sigmaI/netI    0.0856
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            20515
_diffrn_reflns_theta_full        28.50
_diffrn_reflns_theta_max         28.50
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    1.372
_exptl_absorpt_correction_T_max  0.7806
_exptl_absorpt_correction_T_min  0.7000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 - Bruker AXS'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             932
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.934
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         5052
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0313P)²+1.5744P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1199
_reflns_number_gt                3881
_reflns_number_total             5052
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C4.cif
_cod_data_source_block           n16_a85
_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        2001.8(6)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1556620
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
Cu1 Cu 0.51148(2) 0.69405(4) 0.23374(2) 0.01551(11) Uani 1 1 d . . .
Cl1 Cl 0.58496(5) 0.82684(9) 0.16219(5) 0.02592(18) Uani 1 1 d . . .
N1 N 0.35612(17) 0.7779(3) 0.01640(15) 0.0179(5) Uani 1 1 d . . .
C1 C 0.3453(2) 0.9201(4) -0.0384(2) 0.0238(7) Uani 1 1 d . . .
H1A H 0.2775 0.9392 -0.0746 0.029 Uiso 1 1 calc R . .
H1B H 0.3828 0.9056 -0.0728 0.029 Uiso 1 1 calc R . .
C17 C 0.6261(2) 0.3677(4) 0.20876(19) 0.0235(6) Uani 1 1 d . . .
H17A H 0.6869 0.3314 0.2075 0.035 Uiso 1 1 calc R . .
H17B H 0.6174 0.4859 0.1962 0.035 Uiso 1 1 calc R . .
H17C H 0.5737 0.3058 0.1677 0.035 Uiso 1 1 calc R . .
N2 N 0.37290(16) 0.9946(3) 0.09641(16) 0.0176(5) Uani 1 1 d . . .
Cl2 Cl 0.60867(5) 0.76459(9) 0.36300(5) 0.02640(18) Uani 1 1 d . . .
C2 C 0.3849(2) 1.0600(3) 0.02365(19) 0.0223(6) Uani 1 1 d . . .
H2A H 0.4530 1.0812 0.0351 0.027 Uiso 1 1 calc R . .
H2B H 0.3481 1.1631 0.0040 0.027 Uiso 1 1 calc R . .
N3 N 0.37684(16) 0.7311(3) 0.15685(15) 0.0156(5) Uani 1 1 d . . .
C3 C 0.4010(2) 1.0875(4) 0.1725(2) 0.0252(7) Uani 1 1 d . . .
H3A H 0.3774 1.0318 0.2101 0.038 Uiso 1 1 calc R . .
H3B H 0.3739 1.1989 0.1606 0.038 Uiso 1 1 calc R . .
H3C H 0.4708 1.0949 0.1982 0.038 Uiso 1 1 calc R . .
C5 C 0.36812(18) 0.8281(3) 0.09206(18) 0.0149(5) Uani 1 1 d . . .
N5 N 0.56076(17) 0.2921(3) 0.38157(15) 0.0174(5) Uani 1 1 d . . .
N4 N 0.48259(16) 0.4757(3) 0.26633(15) 0.0152(5) Uani 1 1 d . . .
C4 C 0.3566(2) 0.6086(3) -0.0093(2) 0.0226(6) Uani 1 1 d . . .
H4A H 0.3703 0.5353 0.0382 0.034 Uiso 1 1 calc R . .
H4B H 0.4057 0.5947 -0.0317 0.034 Uiso 1 1 calc R . .
H4C H 0.2940 0.5810 -0.0518 0.034 Uiso 1 1 calc R . .
C6 C 0.29846(19) 0.6261(3) 0.14640(17) 0.0145(5) Uani 1 1 d . . .
N6 N 0.62666(17) 0.3381(3) 0.29010(16) 0.0187(5) Uani 1 1 d . . .
C7 C 0.2096(2) 0.6489(3) 0.08184(19) 0.0172(6) Uani 1 1 d . . .
H7 H 0.2030 0.7313 0.0416 0.021 Uiso 1 1 calc R . .
C8 C 0.1310(2) 0.5545(4) 0.07502(19) 0.0196(6) Uani 1 1 d . . .
H8 H 0.0716 0.5728 0.0304 0.024 Uiso 1 1 calc R . .
C9 C 0.1387(2) 0.4337(4) 0.1329(2) 0.0222(6) Uani 1 1 d . . .
H9 H 0.0850 0.3687 0.1284 0.027 Uiso 1 1 calc R . .
C10 C 0.2263(2) 0.4096(3) 0.1973(2) 0.0198(6) Uani 1 1 d . . .
H10 H 0.2320 0.3263 0.2369 0.024 Uiso 1 1 calc R . .
C11 C 0.30649(19) 0.5042(3) 0.20594(18) 0.0160(6) Uani 1 1 d . . .
C12 C 0.39518(19) 0.4798(3) 0.28314(18) 0.0177(6) Uani 1 1 d . . .
H12A H 0.4002 0.5707 0.3222 0.021 Uiso 1 1 calc R . .
H12B H 0.3896 0.3749 0.3098 0.021 Uiso 1 1 calc R . .
C13 C 0.55258(19) 0.3762(3) 0.31126(18) 0.0160(6) Uani 1 1 d . . .
C14 C 0.5413(2) 0.3759(4) 0.44713(19) 0.0242(7) Uani 1 1 d . . .
H14A H 0.5806 0.3268 0.5005 0.036 Uiso 1 1 calc R . .
H14B H 0.4737 0.3634 0.4372 0.036 Uiso 1 1 calc R . .
H14C H 0.5567 0.4934 0.4475 0.036 Uiso 1 1 calc R . .
C15 C 0.6495(2) 0.1950(4) 0.4106(2) 0.0230(6) Uani 1 1 d . . .
H15A H 0.6384 0.0814 0.4255 0.028 Uiso 1 1 calc R . .
H15B H 0.6994 0.2478 0.4591 0.028 Uiso 1 1 calc R . .
C16 C 0.6781(2) 0.1942(3) 0.33688(19) 0.0208(6) Uani 1 1 d . . .
H16A H 0.7479 0.2071 0.3544 0.025 Uiso 1 1 calc R . .
H16B H 0.6573 0.0914 0.3044 0.025 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'
Cl Cl 0.1484 0.1585 '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
N4 Cu1 N3 92.62(9) . .
N4 Cu1 Cl2 93.81(7) . .
N3 Cu1 Cl2 138.18(7) . .
N4 Cu1 Cl1 144.04(7) . .
N3 Cu1 Cl1 98.73(7) . .
Cl2 Cu1 Cl1 99.85(3) . .
C5 N1 C4 125.9(2) . .
C5 N1 C1 110.7(2) . .
C4 N1 C1 123.4(2) . .
N1 C1 C2 101.5(2) . .
N1 C1 H1A 111.5 . .
C2 C1 H1A 111.5 . .
N1 C1 H1B 111.5 . .
C2 C1 H1B 111.5 . .
H1A C1 H1B 109.3 . .
N6 C17 H17A 109.5 . .
N6 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
N6 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C5 N2 C3 124.1(3) . .
C5 N2 C2 109.5(2) . .
C3 N2 C2 122.0(2) . .
N2 C2 C1 102.1(2) . .
N2 C2 H2A 111.4 . .
C1 C2 H2A 111.4 . .
N2 C2 H2B 111.4 . .
C1 C2 H2B 111.4 . .
H2A C2 H2B 109.2 . .
C5 N3 C6 116.2(2) . .
C5 N3 Cu1 113.45(17) . .
C6 N3 Cu1 126.10(18) . .
N2 C3 H3A 109.5 . .
N2 C3 H3B 109.5 . .
H3A C3 H3B 109.5 . .
N2 C3 H3C 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
N1 C5 N3 126.6(2) . .
N1 C5 N2 110.1(2) . .
N3 C5 N2 123.2(3) . .
C13 N5 C14 120.4(2) . .
C13 N5 C15 108.9(2) . .
C14 N5 C15 114.5(2) . .
C13 N4 C12 118.2(2) . .
C13 N4 Cu1 120.22(18) . .
C12 N4 Cu1 111.25(17) . .
N1 C4 H4A 109.5 . .
N1 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
N1 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C7 C6 C11 118.2(2) . .
C7 C6 N3 121.6(2) . .
C11 C6 N3 120.0(2) . .
C13 N6 C17 123.5(2) . .
C13 N6 C16 110.2(2) . .
C17 N6 C16 118.9(2) . .
C8 C7 C6 121.7(3) . .
C8 C7 H7 119.1 . .
C6 C7 H7 119.1 . .
C9 C8 C7 120.4(3) . .
C9 C8 H8 119.8 . .
C7 C8 H8 119.8 . .
C8 C9 C10 118.7(3) . .
C8 C9 H9 120.7 . .
C10 C9 H9 120.7 . .
C9 C10 C11 122.1(3) . .
C9 C10 H10 119.0 . .
C11 C10 H10 119.0 . .
C10 C11 C6 119.0(3) . .
C10 C11 C12 117.5(3) . .
C6 C11 C12 123.3(2) . .
N4 C12 C11 112.5(2) . .
N4 C12 H12A 109.1 . .
C11 C12 H12A 109.1 . .
N4 C12 H12B 109.1 . .
C11 C12 H12B 109.1 . .
H12A C12 H12B 107.8 . .
N4 C13 N6 122.4(3) . .
N4 C13 N5 127.4(2) . .
N6 C13 N5 110.1(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 . .
N5 C15 C16 103.6(2) . .
N5 C15 H15A 111.0 . .
C16 C15 H15A 111.0 . .
N5 C15 H15B 111.0 . .
C16 C15 H15B 111.0 . .
H15A C15 H15B 109.0 . .
N6 C16 C15 102.0(2) . .
N6 C16 H16A 111.4 . .
C15 C16 H16A 111.4 . .
N6 C16 H16B 111.4 . .
C15 C16 H16B 111.4 . .
H16A C16 H16B 109.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N4 1.963(2) .
Cu1 N3 1.989(2) .
Cu1 Cl2 2.2512(9) .
Cu1 Cl1 2.2601(8) .
N1 C5 1.337(4) .
N1 C4 1.445(4) .
N1 C1 1.471(4) .
C1 C2 1.526(4) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C17 N6 1.451(4) .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
N2 C5 1.351(3) .
N2 C3 1.449(4) .
N2 C2 1.464(4) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
N3 C5 1.350(4) .
N3 C6 1.418(3) .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 0.9800 .
N5 C13 1.377(4) .
N5 C14 1.467(4) .
N5 C15 1.472(4) .
N4 C13 1.323(3) .
N4 C12 1.474(3) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C6 C7 1.398(4) .
C6 C11 1.412(4) .
N6 C13 1.356(3) .
N6 C16 1.465(4) .
C7 C8 1.386(4) .
C7 H7 0.9500 .
C8 C9 1.385(4) .
C8 H8 0.9500 .
C9 C10 1.386(4) .
C9 H9 0.9500 .
C10 C11 1.399(4) .
C10 H10 0.9500 .
C11 C12 1.509(4) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 C16 1.524(4) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 H16A 0.9900 .
C16 H16B 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
C5 N1 C1 C2 17.8(3) . . . .
C4 N1 C1 C2 -160.4(3) . . . .
C5 N2 C2 C1 22.9(3) . . . .
C3 N2 C2 C1 -179.7(2) . . . .
N1 C1 C2 N2 -23.3(3) . . . .
N4 Cu1 N3 C5 -150.3(2) . . . .
Cl2 Cu1 N3 C5 111.07(19) . . . .
Cl1 Cu1 N3 C5 -4.48(19) . . . .
N4 Cu1 N3 C6 5.4(2) . . . .
Cl2 Cu1 N3 C6 -93.3(2) . . . .
Cl1 Cu1 N3 C6 151.2(2) . . . .
C4 N1 C5 N3 -4.5(4) . . . .
C1 N1 C5 N3 177.5(3) . . . .
C4 N1 C5 N2 174.0(2) . . . .
C1 N1 C5 N2 -4.0(3) . . . .
C6 N3 C5 N1 -60.6(4) . . . .
Cu1 N3 C5 N1 97.6(3) . . . .
C6 N3 C5 N2 121.1(3) . . . .
Cu1 N3 C5 N2 -80.7(3) . . . .
C3 N2 C5 N1 -169.5(2) . . . .
C2 N2 C5 N1 -12.7(3) . . . .
C3 N2 C5 N3 9.1(4) . . . .
C2 N2 C5 N3 165.9(2) . . . .
N3 Cu1 N4 C13 170.2(2) . . . .
Cl2 Cu1 N4 C13 -51.1(2) . . . .
Cl1 Cu1 N4 C13 61.4(3) . . . .
N3 Cu1 N4 C12 -45.31(19) . . . .
Cl2 Cu1 N4 C12 93.34(18) . . . .
Cl1 Cu1 N4 C12 -154.09(14) . . . .
C5 N3 C6 C7 -14.6(4) . . . .
Cu1 N3 C6 C7 -169.7(2) . . . .
C5 N3 C6 C11 171.0(2) . . . .
Cu1 N3 C6 C11 16.0(3) . . . .
C11 C6 C7 C8 -0.6(4) . . . .
N3 C6 C7 C8 -175.1(3) . . . .
C6 C7 C8 C9 0.0(4) . . . .
C7 C8 C9 C10 0.0(4) . . . .
C8 C9 C10 C11 0.5(4) . . . .
C9 C10 C11 C6 -1.1(4) . . . .
C9 C10 C11 C12 173.6(3) . . . .
C7 C6 C11 C10 1.1(4) . . . .
N3 C6 C11 C10 175.6(2) . . . .
C7 C6 C11 C12 -173.3(2) . . . .
N3 C6 C11 C12 1.3(4) . . . .
C13 N4 C12 C11 -144.8(2) . . . .
Cu1 N4 C12 C11 69.9(2) . . . .
C10 C11 C12 N4 138.0(2) . . . .
C6 C11 C12 N4 -47.6(3) . . . .
C12 N4 C13 N6 166.2(3) . . . .
Cu1 N4 C13 N6 -51.7(3) . . . .
C12 N4 C13 N5 -10.8(4) . . . .
Cu1 N4 C13 N5 131.2(2) . . . .
C17 N6 C13 N4 -15.3(4) . . . .
C16 N6 C13 N4 -164.6(3) . . . .
C17 N6 C13 N5 162.1(3) . . . .
C16 N6 C13 N5 12.9(3) . . . .
C14 N5 C13 N4 -45.4(4) . . . .
C15 N5 C13 N4 179.5(3) . . . .
C14 N5 C13 N6 137.3(3) . . . .
C15 N5 C13 N6 2.1(3) . . . .
C13 N5 C15 C16 -15.2(3) . . . .
C14 N5 C15 C16 -153.2(2) . . . .
C13 N6 C16 C15 -21.4(3) . . . .
C17 N6 C16 C15 -172.3(3) . . . .
N5 C15 C16 N6 21.2(3) . . . .
