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#$Date: 2020-08-22 00:35:06 +0300 (Sat, 22 Aug 2020) $
#$Revision: 255512 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/79/4517975.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_4517975
loop_
_publ_author_name
'Astaf’eva, Tatiana V.'
'Arsenyev, Maxim V.'
'Rumyantcev, Roman V.'
'Fukin, Georgy K.'
'Cherkasov, Vladimir K.'
'Poddel’sky, Andrey I.'
_publ_section_title
;
 Imine-Based Catechols and o-Benzoquinones: Synthesis, Structure, and
 Features of Redox Behavior
;
_journal_name_full               'ACS Omega'
_journal_paper_doi               10.1021/acsomega.0c02277
_journal_year                    2020
_chemical_formula_sum            'C21 H27 N O2'
_chemical_formula_weight         325.43
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                77.457(2)
_cell_angle_beta                 89.145(2)
_cell_angle_gamma                63.858(2)
_cell_formula_units_Z            2
_cell_length_a                   8.8570(12)
_cell_length_b                   9.1079(12)
_cell_length_c                   13.0615(17)
_cell_measurement_reflns_used    3767
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.48
_cell_measurement_theta_min      2.70
_cell_volume                     919.4(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Quest with CMOS Detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6140
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         2.563
_diffrn_source                   'microfocus tube'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9867
_exptl_absorpt_correction_T_min  0.8994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/2'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_description       plate
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3987
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0437
_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)+(0.0615P)²+0.2060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1188
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3253
_reflns_number_total             3987
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao0c02277_si_001.cif
_cod_data_source_block           4
_cod_database_code               4517975
_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.
;
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.992
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
O1 O 0.32484(10) 0.64879(12) 0.01437(7) 0.0203(2) Uani 1 1 d . . . . .
H1 H 0.236(2) 0.735(2) -0.0444(12) 0.024 Uiso 1 1 d . U . . .
O2 O 0.49050(10) 0.40945(12) 0.17993(8) 0.0240(2) Uani 1 1 d . . . . .
H2 H 0.510(2) 0.451(2) 0.1175(14) 0.029 Uiso 1 1 d . U . . .
N1 N 0.06266(12) 0.84101(13) -0.09934(8) 0.0188(2) Uani 1 1 d . . . . .
C1 C 0.22934(15) 0.61186(16) 0.08634(10) 0.0171(3) Uani 1 1 d . . . . .
C2 C 0.31717(14) 0.48583(16) 0.17638(10) 0.0184(3) Uani 1 1 d . . . . .
C3 C 0.23169(15) 0.44215(16) 0.25746(10) 0.0183(3) Uani 1 1 d . . . . .
C4 C 0.05340(15) 0.52932(16) 0.24356(10) 0.0194(3) Uani 1 1 d . . . . .
H4A H -0.0068 0.5035 0.2998 0.023 Uiso 1 1 calc R U . . .
C5 C -0.03980(14) 0.64865(16) 0.15491(10) 0.0174(3) Uani 1 1 d . . . . .
C6 C 0.05051(14) 0.69061(15) 0.07176(9) 0.0163(3) Uani 1 1 d . . . . .
C7 C 0.32390(16) 0.30287(17) 0.35609(10) 0.0217(3) Uani 1 1 d . . . . .
C8 C 0.44815(17) 0.34123(18) 0.41300(11) 0.0275(3) Uani 1 1 d . . . . .
H8A H 0.5261 0.3595 0.3637 0.041 Uiso 1 1 calc R U . . .
H8B H 0.5123 0.2460 0.4722 0.041 Uiso 1 1 calc R U . . .
H8C H 0.3853 0.4426 0.4393 0.041 Uiso 1 1 calc R U . . .
C9 C 0.41989(19) 0.13634(18) 0.32301(12) 0.0302(3) Uani 1 1 d . . . . .
H9A H 0.3398 0.1106 0.2887 0.045 Uiso 1 1 calc R U . . .
H9B H 0.4799 0.0460 0.3854 0.045 Uiso 1 1 calc R U . . .
H9C H 0.5014 0.1460 0.2737 0.045 Uiso 1 1 calc R U . . .
C10 C 0.20164(18) 0.2810(2) 0.43541(12) 0.0334(4) Uani 1 1 d . . . . .
H10A H 0.1237 0.2510 0.4025 0.050 Uiso 1 1 calc R U . . .
H10B H 0.1373 0.3866 0.4571 0.050 Uiso 1 1 calc R U . . .
H10C H 0.2658 0.1914 0.4973 0.050 Uiso 1 1 calc R U . . .
C11 C -0.23457(15) 0.72814(17) 0.14782(10) 0.0209(3) Uani 1 1 d . . . . .
C12 C -0.30004(16) 0.66925(18) 0.06449(11) 0.0258(3) Uani 1 1 d . . . . .
H12A H -0.4234 0.7172 0.0619 0.039 Uiso 1 1 calc R U . . .
H12B H -0.2513 0.5462 0.0829 0.039 Uiso 1 1 calc R U . . .
H12C H -0.2672 0.7067 -0.0046 0.039 Uiso 1 1 calc R U . . .
C13 C -0.31436(16) 0.92140(18) 0.12465(12) 0.0264(3) Uani 1 1 d . . . . .
H13A H -0.4376 0.9671 0.1218 0.040 Uiso 1 1 calc R U . . .
H13B H -0.2822 0.9647 0.0569 0.040 Uiso 1 1 calc R U . . .
H13C H -0.2741 0.9555 0.1806 0.040 Uiso 1 1 calc R U . . .
C14 C -0.29861(17) 0.6734(2) 0.25193(12) 0.0347(4) Uani 1 1 d . . . . .
H14A H -0.4223 0.7315 0.2458 0.052 Uiso 1 1 calc R U . . .
H14B H -0.2539 0.7021 0.3088 0.052 Uiso 1 1 calc R U . . .
H14C H -0.2605 0.5516 0.2677 0.052 Uiso 1 1 calc R U . . .
C15 C -0.02665(15) 0.80353(15) -0.02889(10) 0.0176(3) Uani 1 1 d . . . . .
H15A H -0.1456 0.8514 -0.0438 0.021 Uiso 1 1 calc R U . . .
C16 C -0.00748(15) 0.94959(16) -0.19925(10) 0.0180(3) Uani 1 1 d . . . . .
C17 C 0.09613(16) 0.92313(17) -0.28140(10) 0.0214(3) Uani 1 1 d . . . . .
H17A H 0.2063 0.8316 -0.2696 0.026 Uiso 1 1 calc R U . . .
C18 C 0.03854(17) 1.03015(18) -0.38003(11) 0.0254(3) Uani 1 1 d . . . . .
H18A H 0.1093 1.0122 -0.4360 0.031 Uiso 1 1 calc R U . . .
C19 C -0.12174(18) 1.16336(18) -0.39761(11) 0.0266(3) Uani 1 1 d . . . . .
H19A H -0.1611 1.2368 -0.4656 0.032 Uiso 1 1 calc R U . . .
C20 C -0.22502(17) 1.18955(17) -0.31584(11) 0.0252(3) Uani 1 1 d . . . . .
H20A H -0.3354 1.2807 -0.3282 0.030 Uiso 1 1 calc R U . . .
C21 C -0.16847(15) 1.08408(16) -0.21662(10) 0.0207(3) Uani 1 1 d . . . . .
H21A H -0.2391 1.1033 -0.1606 0.025 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 0.0033 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
C1 O1 H1 101.9(8) . . ?
C2 O2 H2 103.2(11) . . ?
C15 N1 C16 123.17(10) . . ?
C15 N1 H1 100.5(6) . . ?
C16 N1 H1 136.2(6) . . ?
O1 C1 C2 115.94(10) . . ?
O1 C1 C6 122.69(11) . . ?
C2 C1 C6 121.34(11) . . ?
O2 C2 C3 122.23(11) . . ?
O2 C2 C1 116.89(10) . . ?
C3 C2 C1 120.87(11) . . ?
C2 C3 C4 116.59(11) . . ?
C2 C3 C7 122.13(11) . . ?
C4 C3 C7 121.26(11) . . ?
C5 C4 C3 125.10(11) . . ?
C5 C4 H4A 117.5 . . ?
C3 C4 H4A 117.5 . . ?
C4 C5 C6 117.45(10) . . ?
C4 C5 C11 119.78(11) . . ?
C6 C5 C11 122.75(11) . . ?
C1 C6 C5 118.45(11) . . ?
C1 C6 C15 116.88(10) . . ?
C5 C6 C15 124.62(10) . . ?
C3 C7 C9 108.56(11) . . ?
C3 C7 C10 112.19(10) . . ?
C9 C7 C10 107.82(12) . . ?
C3 C7 C8 111.10(11) . . ?
C9 C7 C8 109.74(11) . . ?
C10 C7 C8 107.35(11) . . ?
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 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C14 C11 C12 106.42(11) . . ?
C14 C11 C13 105.54(11) . . ?
C12 C11 C13 111.21(11) . . ?
C14 C11 C5 111.81(11) . . ?
C12 C11 C5 109.84(10) . . ?
C13 C11 C5 111.84(10) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 C6 121.31(11) . . ?
N1 C15 H15A 119.3 . . ?
C6 C15 H15A 119.3 . . ?
C21 C16 C17 119.96(12) . . ?
C21 C16 N1 123.08(11) . . ?
C17 C16 N1 116.86(11) . . ?
C18 C17 C16 119.90(12) . . ?
C18 C17 H17A 120.0 . . ?
C16 C17 H17A 120.0 . . ?
C17 C18 C19 120.23(12) . . ?
C17 C18 H18A 119.9 . . ?
C19 C18 H18A 119.9 . . ?
C18 C19 C20 119.86(12) . . ?
C18 C19 H19A 120.1 . . ?
C20 C19 H19A 120.1 . . ?
C21 C20 C19 120.46(12) . . ?
C21 C20 H20A 119.8 . . ?
C19 C20 H20A 119.8 . . ?
C20 C21 C16 119.58(12) . . ?
C20 C21 H21A 120.2 . . ?
C16 C21 H21A 120.2 . . ?
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 C1 1.3423(14) . ?
O1 H1 1.019(16) . ?
O2 C2 1.3747(14) . ?
O2 H2 0.868(17) . ?
N1 C15 1.2918(16) . ?
N1 C16 1.4104(16) . ?
N1 H1 1.493(16) . ?
C1 C2 1.4000(17) . ?
C1 C6 1.4171(16) . ?
C2 C3 1.3826(17) . ?
C3 C4 1.4135(16) . ?
C3 C7 1.5311(17) . ?
C4 C5 1.3765(17) . ?
C4 H4A 0.9500 . ?
C5 C6 1.4243(16) . ?
C5 C11 1.5439(16) . ?
C6 C15 1.4399(17) . ?
C7 C9 1.5321(19) . ?
C7 C10 1.5339(18) . ?
C7 C8 1.5368(19) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C14 1.5333(18) . ?
C11 C12 1.5346(18) . ?
C11 C13 1.5390(19) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9500 . ?
C16 C21 1.3910(17) . ?
C16 C17 1.3926(17) . ?
C17 C18 1.3806(19) . ?
C17 H17A 0.9500 . ?
C18 C19 1.382(2) . ?
C18 H18A 0.9500 . ?
C19 C20 1.387(2) . ?
C19 H19A 0.9500 . ?
C20 C21 1.3812(18) . ?
C20 H20A 0.9500 . ?
C21 H21A 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.868(17) 2.040(16) 2.6095(13) 122.4(14) .
O1 H1 N1 1.019(16) 1.493(16) 2.4606(13) 156.5(14) .
O2 H2 O1 0.868(17) 2.316(17) 3.0155(13) 137.7(14) 2_665
