#------------------------------------------------------------------------------
#$Date: 2022-07-23 01:46:19 +0300 (Sat, 23 Jul 2022) $
#$Revision: 276801 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/72/1567288.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_1567288
loop_
_publ_author_name
'Heck, Joshua'
'Metz, Fabian'
'Buchenau, Sören'
'Teubner, Melissa'
'Grimm-Lebsanft, Benjamin'
'Spaniol, Thomas P.'
'Hoffmann, Alexander'
'Rübhausen, Michael A.'
'Herres-Pawlis, Sonja'
_publ_section_title
;
 Manipulating electron transfer -- the influence of substituents on novel
 copper guanidine quinolinyl complexes
;
_journal_issue                   28
_journal_name_full               'Chemical Science'
_journal_page_first              8274
_journal_page_last               8288
_journal_paper_doi               10.1039/D2SC02910C
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C18 H26 N4'
_chemical_formula_sum            'C18 H26 N4'
_chemical_formula_weight         298.43
_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   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-01-06 deposited with the CCDC.	2022-07-06 downloaded from the CCDC.
;
_cell_angle_alpha                103.63(3)
_cell_angle_beta                 98.86(3)
_cell_angle_gamma                93.79(3)
_cell_formula_units_Z            2
_cell_length_a                   6.8997(14)
_cell_length_b                   10.446(2)
_cell_length_c                   12.234(2)
_cell_measurement_reflns_used    7175
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.35
_cell_measurement_theta_min      3.77
_cell_volume                     841.9(3)
_computing_cell_refinement
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection
;
X-Area Pilatus3_SV 1.31.131.0 (STOE, 2017)
;
_computing_data_reduction
;
X-Area Integrate 1.71.0.0 (STOE, 2016)
X-Area LANA 1.71.4.0 (STOE, 2017)
;
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.77, Darmstadt 2016
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Hybrid Pixel Counting Detector'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'Dectris Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.872
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_details      ' 3434 frames, detector distance = 60 mm'
_diffrn_measurement_device       '4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '0.5 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 0.872
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4739
_diffrn_reflns_point_group_measured_fraction_full 0.872
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         67.811
_diffrn_reflns_theta_min         3.776
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_source_target            Cu
_diffrn_source_type              'Xenocs Cu microfocus tube'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.553
_exptl_absorpt_correction_T_max  0.9689
_exptl_absorpt_correction_T_min  0.0141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_description       plate
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2782
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0507
_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)+(0.0633P)²+0.4502P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1370
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2460
_reflns_number_total             2782
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc02910c2.cif
_cod_data_source_block           L3
_cod_database_code               1567288
_shelx_shelxl_version_number     2018/3
_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   0.932
_shelx_estimated_absorpt_t_max   0.989
_exptl_absorpt_special_details
;
Afterwards scaling of reflection intensities was performed within STOE LANA.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7775(2) 0.62880(14) 0.42378(12) 0.0267(3) Uani 1 1 d . . . . .
C1 C 0.6175(3) 0.68725(17) 0.42747(14) 0.0266(4) Uani 1 1 d . . . . .
N3 N 0.4294(2) 0.63169(15) 0.37923(13) 0.0289(4) Uani 1 1 d . . . . .
C3 C 0.5123(3) 0.8525(2) 0.57903(17) 0.0374(5) Uani 1 1 d . . . . .
H3A H 0.486896 0.945440 0.589671 0.056 Uiso 1 1 calc R U . . .
H3B H 0.584085 0.839516 0.650538 0.056 Uiso 1 1 calc R U . . .
H3C H 0.386574 0.795773 0.557256 0.056 Uiso 1 1 calc R U . . .
N2 N 0.6301(2) 0.81786(15) 0.48924(13) 0.0301(4) Uani 1 1 d . . . . .
C2 C 0.8254(3) 0.89019(19) 0.51726(18) 0.0371(5) Uani 1 1 d . . . . .
H2A H 0.890052 0.871112 0.450154 0.056 Uiso 1 1 calc R U . . .
H2B H 0.903861 0.862867 0.580052 0.056 Uiso 1 1 calc R U . . .
H2C H 0.814144 0.985427 0.540489 0.056 Uiso 1 1 calc R U . . .
C5 C 0.3784(3) 0.48905(18) 0.34729(16) 0.0315(4) Uani 1 1 d . . . . .
H5A H 0.394645 0.453519 0.268016 0.047 Uiso 1 1 calc R U . . .
H5B H 0.240938 0.468841 0.354593 0.047 Uiso 1 1 calc R U . . .
H5C H 0.465170 0.448579 0.397708 0.047 Uiso 1 1 calc R U . . .
N4 N 0.7497(2) 0.66613(15) 0.20505(12) 0.0265(3) Uani 1 1 d . . . . .
C4 C 0.2778(3) 0.7074(2) 0.33600(17) 0.0352(5) Uani 1 1 d . . . . .
H4A H 0.231766 0.668586 0.254224 0.053 Uiso 1 1 calc R U . . .
H4B H 0.333277 0.799479 0.347883 0.053 Uiso 1 1 calc R U . . .
H4C H 0.166699 0.705066 0.376924 0.053 Uiso 1 1 calc R U . . .
C7 C 0.7453(3) 0.5833(2) 0.00484(16) 0.0331(4) Uani 1 1 d . . . . .
H7 H 0.731130 0.600002 -0.068874 0.040 Uiso 1 1 calc R U . . .
C6 C 0.7414(2) 0.68736(19) 0.10191(15) 0.0283(4) Uani 1 1 d . . . . .
C9 C 0.7903(3) 0.43413(18) 0.12719(16) 0.0294(4) Uani 1 1 d . . . . .
C8 C 0.7696(3) 0.4587(2) 0.01765(16) 0.0337(4) Uani 1 1 d . . . . .
H8 H 0.772629 0.388485 -0.047294 0.040 Uiso 1 1 calc R U . . .
C10 C 0.8316(3) 0.31008(19) 0.14895(17) 0.0327(4) Uani 1 1 d . . . . .
H10 H 0.839459 0.236630 0.087540 0.039 Uiso 1 1 calc R U . . .
C11 C 0.8600(3) 0.29698(19) 0.25857(17) 0.0332(4) Uani 1 1 d . . . . .
H11 H 0.891869 0.214734 0.273023 0.040 Uiso 1 1 calc R U . . .
C12 C 0.8429(3) 0.40253(18) 0.34991(16) 0.0303(4) Uani 1 1 d . . . . .
H12 H 0.867044 0.391210 0.425452 0.036 Uiso 1 1 calc R U . . .
C13 C 0.7916(2) 0.52331(18) 0.33276(15) 0.0259(4) Uani 1 1 d . . . . .
C14 C 0.7732(2) 0.54196(17) 0.21903(15) 0.0254(4) Uani 1 1 d . . . . .
C15 C 0.7411(3) 0.83209(19) 0.09721(15) 0.0305(4) Uani 1 1 d . . . . .
C16 C 0.6968(3) 0.8488(2) -0.02509(17) 0.0376(5) Uani 1 1 d . . . . .
H16A H 0.799296 0.813078 -0.067129 0.056 Uiso 1 1 calc R U . . .
H16B H 0.694717 0.943078 -0.022933 0.056 Uiso 1 1 calc R U . . .
H16C H 0.568122 0.800962 -0.063350 0.056 Uiso 1 1 calc R U . . .
C17 C 0.9485(3) 0.9021(2) 0.15306(17) 0.0364(5) Uani 1 1 d . . . . .
H17A H 1.046534 0.859756 0.110771 0.055 Uiso 1 1 calc R U . . .
H17B H 0.977385 0.895402 0.232378 0.055 Uiso 1 1 calc R U . . .
H17C H 0.953482 0.995618 0.151562 0.055 Uiso 1 1 calc R U . . .
C18 C 0.5894(3) 0.8977(2) 0.16558(18) 0.0386(5) Uani 1 1 d . . . . .
H18A H 0.598175 0.992403 0.167930 0.058 Uiso 1 1 calc R U . . .
H18B H 0.616777 0.886524 0.243585 0.058 Uiso 1 1 calc R U . . .
H18C H 0.456441 0.856190 0.128819 0.058 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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
C1 N1 C13 121.13(15) . . ?
N1 C1 N3 126.69(16) . . ?
N1 C1 N2 119.02(16) . . ?
N3 C1 N2 114.23(16) . . ?
C1 N3 C5 121.53(16) . . ?
C1 N3 C4 122.51(16) . . ?
C5 N3 C4 114.89(15) . . ?
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 . . ?
C1 N2 C2 115.80(16) . . ?
C1 N2 C3 119.25(15) . . ?
C2 N2 C3 113.61(16) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N3 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C6 N4 C14 119.17(16) . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C8 C7 C6 119.61(17) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
N4 C6 C7 121.74(17) . . ?
N4 C6 C15 115.32(16) . . ?
C7 C6 C15 122.82(16) . . ?
C8 C9 C14 116.72(17) . . ?
C8 C9 C10 123.55(17) . . ?
C14 C9 C10 119.70(17) . . ?
C7 C8 C9 120.10(17) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C11 C10 C9 119.67(17) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 121.15(18) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 121.51(17) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 N1 121.46(16) . . ?
C12 C13 C14 118.16(17) . . ?
N1 C13 C14 120.06(16) . . ?
N4 C14 C9 122.45(16) . . ?
N4 C14 C13 117.93(16) . . ?
C9 C14 C13 119.53(16) . . ?
C6 C15 C16 112.96(16) . . ?
C6 C15 C18 109.89(15) . . ?
C16 C15 C18 109.34(16) . . ?
C6 C15 C17 107.31(15) . . ?
C16 C15 C17 108.30(16) . . ?
C18 C15 C17 108.93(17) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
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
N1 C1 1.298(2) . ?
N1 C13 1.391(2) . ?
C1 N3 1.369(2) . ?
C1 N2 1.385(2) . ?
N3 C5 1.453(2) . ?
N3 C4 1.461(2) . ?
C3 N2 1.458(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
N2 C2 1.451(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
N4 C6 1.325(2) . ?
N4 C14 1.365(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C7 C8 1.365(3) . ?
C7 C6 1.413(3) . ?
C7 H7 0.9500 . ?
C6 C15 1.527(3) . ?
C9 C8 1.411(3) . ?
C9 C14 1.417(3) . ?
C9 C10 1.421(3) . ?
C8 H8 0.9500 . ?
C10 C11 1.366(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.398(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.438(2) . ?
C15 C16 1.534(3) . ?
C15 C18 1.536(3) . ?
C15 C17 1.541(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 N1 C1 N3 28.5(3) . . . . ?
C13 N1 C1 N2 -154.24(16) . . . . ?
N1 C1 N3 C5 19.5(3) . . . . ?
N2 C1 N3 C5 -157.94(16) . . . . ?
N1 C1 N3 C4 -148.14(18) . . . . ?
N2 C1 N3 C4 34.4(2) . . . . ?
N1 C1 N2 C2 17.2(2) . . . . ?
N3 C1 N2 C2 -165.13(16) . . . . ?
N1 C1 N2 C3 -124.08(19) . . . . ?
N3 C1 N2 C3 53.5(2) . . . . ?
C14 N4 C6 C7 3.6(2) . . . . ?
C14 N4 C6 C15 -172.60(14) . . . . ?
C8 C7 C6 N4 -3.8(3) . . . . ?
C8 C7 C6 C15 172.03(17) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C14 C9 C8 C7 3.5(3) . . . . ?
C10 C9 C8 C7 -174.86(17) . . . . ?
C8 C9 C10 C11 176.43(17) . . . . ?
C14 C9 C10 C11 -1.9(3) . . . . ?
C9 C10 C11 C12 2.1(3) . . . . ?
C10 C11 C12 C13 1.7(3) . . . . ?
C11 C12 C13 N1 -179.05(16) . . . . ?
C11 C12 C13 C14 -5.5(3) . . . . ?
C1 N1 C13 C12 -125.13(19) . . . . ?
C1 N1 C13 C14 61.5(2) . . . . ?
C6 N4 C14 C9 0.3(2) . . . . ?
C6 N4 C14 C13 176.97(15) . . . . ?
C8 C9 C14 N4 -3.8(2) . . . . ?
C10 C9 C14 N4 174.57(16) . . . . ?
C8 C9 C14 C13 179.60(16) . . . . ?
C10 C9 C14 C13 -2.0(2) . . . . ?
C12 C13 C14 N4 -171.13(15) . . . . ?
N1 C13 C14 N4 2.5(2) . . . . ?
C12 C13 C14 C9 5.6(2) . . . . ?
N1 C13 C14 C9 179.22(15) . . . . ?
N4 C6 C15 C16 -170.41(15) . . . . ?
C7 C6 C15 C16 13.5(2) . . . . ?
N4 C6 C15 C18 -48.0(2) . . . . ?
C7 C6 C15 C18 135.88(18) . . . . ?
N4 C6 C15 C17 70.30(19) . . . . ?
C7 C6 C15 C17 -105.82(19) . . . . ?
