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#$Date: 2022-07-23 01:46:19 +0300 (Sat, 23 Jul 2022) $
#$Revision: 276801 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/72/1567283.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_1567283
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         'C15 H16 N2 O2'
_chemical_formula_sum            'C15 H16 N2 O2'
_chemical_formula_weight         256.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 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                90
_cell_angle_beta                 108.39(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.4884(17)
_cell_length_b                   6.7183(13)
_cell_length_c                   11.755(2)
_cell_measurement_reflns_used    6316
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.56
_cell_measurement_theta_min      2.54
_cell_volume                     636.1(2)
_computing_cell_refinement
;
X-Area Recipe 1.36.0.0 (STOE, 2020)
;
_computing_data_collection
;
X-Area Pilatus3_SV 1.31.170.0 (STOE, 2020)
;
_computing_data_reduction
;
X-Area Integrate 1.78.3.0 (STOE, 2020)
X-Area LANA 1.83.8.0 (STOE, 2020)
;
_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 1.90, Darmstadt 2020
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_detector                 Pilatus200K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS 200K'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_details      ' 1274 frames, detector distance = 60 mm'
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8322
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.797
_diffrn_reflns_theta_min         2.529
_diffrn_source                   'Genix Mo'
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9896
_exptl_absorpt_correction_T_min  0.3529
_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. Afterwards scaling of
reflection intensities was performed within STOE LANA. J. Koziskova, F. Hahn,
J. Richter, J. Kozisek, Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136-140.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         2549
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0412
_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)+(0.0685P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1213
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1748
_reflns_number_total             2549
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc02910c2.cif
_cod_data_source_block           2cycloHexyl8NO2Qu
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               1567283
_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   0.987
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
O1 O 0.98591(9) 0.41104(12) 0.63124(7) 0.0347(2) Uani 1 1 d . . . . .
N2 N 0.91730(13) 0.250000 0.60336(9) 0.0195(2) Uani 1 2 d S T P . .
C2 C 0.38979(16) 0.250000 0.70738(11) 0.0149(2) Uani 1 2 d S T P . .
H2 H 0.312151 0.250000 0.750526 0.018 Uiso 1 2 calc R U P . .
C3 C 0.33524(15) 0.250000 0.58496(11) 0.0155(2) Uani 1 2 d S T P . .
H3 H 0.219712 0.250000 0.542367 0.019 Uiso 1 2 calc R U P . .
C4 C 0.45277(15) 0.250000 0.52232(10) 0.0128(2) Uani 1 2 d S T P . .
C5 C 0.40878(15) 0.250000 0.39544(10) 0.0155(2) Uani 1 2 d S T P . .
H5 H 0.295035 0.250000 0.348153 0.019 Uiso 1 2 calc R U P . .
C6 C 0.52941(16) 0.250000 0.34064(11) 0.0165(2) Uani 1 2 d S T P . .
H6 H 0.498353 0.250000 0.255601 0.020 Uiso 1 2 calc R U P . .
C7 C 0.69916(17) 0.250000 0.40904(11) 0.0171(3) Uani 1 2 d S T P . .
H7 H 0.782558 0.250000 0.370892 0.021 Uiso 1 2 calc R U P . .
C8 C 0.74097(15) 0.250000 0.53072(10) 0.0142(2) Uani 1 2 d S T P . .
C9 C 0.62272(15) 0.250000 0.59278(10) 0.0118(2) Uani 1 2 d S T P . .
C10 C 0.62711(15) 0.250000 0.90561(10) 0.0145(2) Uani 1 2 d S T P . .
H10 H 0.529526 0.250001 0.935966 0.017 Uiso 1 2 calc R U P . .
C11 C 0.73077(12) 0.43751(12) 0.95329(8) 0.0194(2) Uani 1 1 d . . . . .
H11A H 0.821784 0.446389 0.917651 0.023 Uiso 1 1 calc R U . . .
H11B H 0.659683 0.556649 0.927966 0.023 Uiso 1 1 calc R U . . .
C12 C 0.80452(13) 0.43662(13) 1.08958(8) 0.0209(2) Uani 1 1 d . . . . .
H12A H 0.713719 0.443050 1.125536 0.025 Uiso 1 1 calc R U . . .
H12B H 0.875222 0.555844 1.115803 0.025 Uiso 1 1 calc R U . . .
C13 C 0.90796(17) 0.250000 1.13397(11) 0.0188(3) Uani 1 2 d S T P . .
H13A H 1.005245 0.250001 1.104663 0.023 Uiso 1 2 calc R U P . .
H13B H 0.949154 0.250000 1.222704 0.023 Uiso 1 2 calc R U P . .
N1 N 0.67743(12) 0.250000 0.71494(8) 0.0129(2) Uani 1 2 d S T P . .
C1 C 0.56314(15) 0.250000 0.77021(10) 0.0131(2) Uani 1 2 d S T P . .
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'
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
O1 N2 O1 124.34(12) 4_565 . ?
O1 N2 C8 117.83(6) 4_565 . ?
O1 N2 C8 117.83(6) . . ?
C3 C2 C1 119.89(12) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 119.22(12) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 123.52(11) . . ?
C3 C4 C9 116.76(11) . . ?
C5 C4 C9 119.71(11) . . ?
C6 C5 C4 120.40(11) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.80(11) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 118.66(12) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
C7 C8 C9 123.35(11) . . ?
C7 C8 N2 119.37(11) . . ?
C9 C8 N2 117.27(10) . . ?
N1 C9 C8 118.81(11) . . ?
N1 C9 C4 124.12(11) . . ?
C8 C9 C4 117.07(10) . . ?
C1 C10 C11 110.99(7) . 4_565 ?
C1 C10 C11 110.99(7) . . ?
C11 C10 C11 110.03(10) 4_565 . ?
C1 C10 H10 108.2 . . ?
C11 C10 H10 108.2 4_565 . ?
C11 C10 H10 108.2 . . ?
C12 C11 C10 112.20(8) . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C13 111.34(8) . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 C12 110.58(11) 4_565 . ?
C12 C13 H13A 109.5 4_565 . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 4_565 . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C1 N1 C9 117.20(10) . . ?
N1 C1 C2 122.81(11) . . ?
N1 C1 C10 116.13(11) . . ?
C2 C1 C10 121.05(11) . . ?
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
O1 N2 1.2234(9) . ?
N2 C8 1.4707(16) . ?
C2 C3 1.3655(17) . ?
C2 C1 1.4230(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.4146(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.4187(16) . ?
C4 C9 1.4188(16) . ?
C5 C6 1.3710(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.4113(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.3607(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.4148(17) . ?
C9 N1 1.3626(14) . ?
C10 C1 1.5109(16) . ?
C10 C11 1.5376(11) 4_565 ?
C10 C11 1.5376(11) . ?
C10 H10 1.0000 . ?
C11 C12 1.5250(13) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5252(12) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
N1 C1 1.3270(16) . ?
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
C1 C2 C3 C4 0.000(1) . . . . ?
C2 C3 C4 C5 180.000(0) . . . . ?
C2 C3 C4 C9 0.000(1) . . . . ?
C3 C4 C5 C6 180.000(0) . . . . ?
C9 C4 C5 C6 0.000(0) . . . . ?
C4 C5 C6 C7 0.000(0) . . . . ?
C5 C6 C7 C8 0.000(0) . . . . ?
C6 C7 C8 C9 0.000(0) . . . . ?
C6 C7 C8 N2 180.000(0) . . . . ?
O1 N2 C8 C7 -89.77(9) 4_565 . . . ?
O1 N2 C8 C7 89.77(9) . . . . ?
O1 N2 C8 C9 90.23(9) 4_565 . . . ?
O1 N2 C8 C9 -90.23(9) . . . . ?
C7 C8 C9 N1 180.000(0) . . . . ?
N2 C8 C9 N1 0.000(0) . . . . ?
C7 C8 C9 C4 0.000(0) . . . . ?
N2 C8 C9 C4 180.000(0) . . . . ?
C3 C4 C9 N1 0.000(0) . . . . ?
C5 C4 C9 N1 180.000(0) . . . . ?
C3 C4 C9 C8 180.000(0) . . . . ?
C5 C4 C9 C8 0.000(0) . . . . ?
C1 C10 C11 C12 -177.05(8) . . . . ?
C11 C10 C11 C12 -53.81(13) 4_565 . . . ?
C10 C11 C12 C13 55.80(12) . . . . ?
C11 C12 C13 C12 -56.18(14) . . . 4_565 ?
C8 C9 N1 C1 180.000(0) . . . . ?
C4 C9 N1 C1 0.000(1) . . . . ?
C9 N1 C1 C2 0.000(1) . . . . ?
C9 N1 C1 C10 180.000(0) . . . . ?
C3 C2 C1 N1 0.000(1) . . . . ?
C3 C2 C1 C10 180.000(1) . . . . ?
C11 C10 C1 N1 -61.34(7) 4_565 . . . ?
C11 C10 C1 N1 61.34(7) . . . . ?
C11 C10 C1 C2 118.66(7) 4_565 . . . ?
C11 C10 C1 C2 -118.66(7) . . . . ?
