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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/4/51/79/4517974.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_4517974
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            'C19 H31 N O2'
_chemical_formula_weight         305.45
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   26.8597(3)
_cell_length_b                   26.8597(3)
_cell_length_c                   14.4115(2)
_cell_measurement_reflns_used    21971
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.3980
_cell_measurement_theta_min      3.6390
_cell_volume                     9004.14(19)
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_refinement  SHELXL-2014/7
_computing_structure_solution    SHELXT-2014/4
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur EOS'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            48489
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         3.034
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.014
_exptl_crystal_description       prism
_exptl_crystal_F_000             3024
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.350
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         4372
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0475P)²+6.8747P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.0985
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3802
_reflns_number_total             4372
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao0c02277_si_001.cif
_cod_data_source_block           3
_cod_original_cell_volume        9004.1(2)
_cod_database_code               4517974
_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   0.962
_shelx_estimated_absorpt_t_max   0.978
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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 0.79235(3) 0.61957(3) 0.23697(4) 0.01688(15) Uani 1 1 d . . . . .
O2 O 0.88225(3) 0.71650(3) 0.29075(5) 0.01858(16) Uani 1 1 d . . . . .
H2 H 0.8697(6) 0.6997(6) 0.2363(11) 0.041(4) Uiso 1 1 d . . . . .
N1 N 0.68978(3) 0.54170(4) 0.25320(6) 0.01738(18) Uani 1 1 d . . . . .
H1 H 0.7260(7) 0.5623(7) 0.2248(10) 0.042(4) Uiso 1 1 d . . . . .
C1 C 0.78803(4) 0.63902(4) 0.31739(6) 0.01429(18) Uani 1 1 d . . . . .
C2 C 0.83675(4) 0.69050(4) 0.35036(6) 0.01513(19) Uani 1 1 d . . . . .
C3 C 0.83798(4) 0.71090(4) 0.43844(6) 0.01569(19) Uani 1 1 d . . . . .
C4 C 0.78698(4) 0.68142(4) 0.49276(6) 0.01652(19) Uani 1 1 d . . . . .
H4A H 0.7877 0.6955 0.5535 0.020 Uiso 1 1 calc R U . . .
C5 C 0.73695(4) 0.63415(4) 0.46395(6) 0.01555(19) Uani 1 1 d . . . . .
C6 C 0.73706(4) 0.61163(4) 0.37313(6) 0.01499(19) Uani 1 1 d . . . . .
C7 C 0.89238(4) 0.76282(4) 0.47746(7) 0.0196(2) Uani 1 1 d . . . . .
C8 C 0.94295(4) 0.75104(5) 0.47181(7) 0.0249(2) Uani 1 1 d . . . . .
H8A H 0.9508 0.7470 0.4067 0.037 Uiso 1 1 calc R U . . .
H8B H 0.9330 0.7155 0.5053 0.037 Uiso 1 1 calc R U . . .
H8C H 0.9772 0.7832 0.4998 0.037 Uiso 1 1 calc R U . . .
C9 C 0.88570(5) 0.77467(5) 0.57970(7) 0.0258(2) Uani 1 1 d . . . . .
H9A H 0.8545 0.7833 0.5855 0.039 Uiso 1 1 calc R U . . .
H9B H 0.9216 0.8075 0.6018 0.039 Uiso 1 1 calc R U . . .
H9C H 0.8767 0.7407 0.6170 0.039 Uiso 1 1 calc R U . . .
C10 C 0.90624(5) 0.81690(4) 0.42144(7) 0.0252(2) Uani 1 1 d . . . . .
H10A H 0.8754 0.8259 0.4299 0.038 Uiso 1 1 calc R U . . .
H10B H 0.9095 0.8100 0.3555 0.038 Uiso 1 1 calc R U . . .
H10C H 0.9427 0.8493 0.4432 0.038 Uiso 1 1 calc R U . . .
C11 C 0.68343(4) 0.60768(4) 0.52714(6) 0.0184(2) Uani 1 1 d . . . . .
C12 C 0.63498(4) 0.61433(5) 0.48214(7) 0.0237(2) Uani 1 1 d . . . . .
H12A H 0.6483 0.6552 0.4724 0.035 Uiso 1 1 calc R U . . .
H12B H 0.6013 0.5977 0.5231 0.035 Uiso 1 1 calc R U . . .
H12C H 0.6245 0.5943 0.4223 0.035 Uiso 1 1 calc R U . . .
C13 C 0.66298(5) 0.54419(5) 0.55047(7) 0.0247(2) Uani 1 1 d . . . . .
H13A H 0.6947 0.5413 0.5787 0.037 Uiso 1 1 calc R U . . .
H13B H 0.6506 0.5212 0.4935 0.037 Uiso 1 1 calc R U . . .
H13C H 0.6307 0.5297 0.5940 0.037 Uiso 1 1 calc R U . . .
C14 C 0.69580(5) 0.63882(5) 0.62113(7) 0.0243(2) Uani 1 1 d . . . . .
H14A H 0.7070 0.6792 0.6110 0.036 Uiso 1 1 calc R U . . .
H14B H 0.7271 0.6367 0.6525 0.036 Uiso 1 1 calc R U . . .
H14C H 0.6612 0.6204 0.6598 0.036 Uiso 1 1 calc R U . . .
C15 C 0.68837(4) 0.56327(4) 0.33342(6) 0.0169(2) Uani 1 1 d . . . . .
H15A H 0.6532 0.5459 0.3670 0.020 Uiso 1 1 calc R U . . .
C16 C 0.63966(4) 0.49293(4) 0.20757(7) 0.0222(2) Uani 1 1 d . . . . .
C17 C 0.66358(5) 0.47635(6) 0.12494(9) 0.0390(3) Uani 1 1 d . . . . .
H17A H 0.6900 0.4638 0.1469 0.059 Uiso 1 1 calc R U . . .
H17B H 0.6842 0.5096 0.0839 0.059 Uiso 1 1 calc R U . . .
H17C H 0.6319 0.4450 0.0907 0.059 Uiso 1 1 calc R U . . .
C18 C 0.59867(5) 0.51317(5) 0.17458(8) 0.0321(3) Uani 1 1 d . . . . .
H18A H 0.6184 0.5445 0.1297 0.048 Uiso 1 1 calc R U . . .
H18B H 0.5862 0.5270 0.2278 0.048 Uiso 1 1 calc R U . . .
H18C H 0.5650 0.4811 0.1451 0.048 Uiso 1 1 calc R U . . .
C19 C 0.60966(5) 0.44291(5) 0.27539(8) 0.0284(2) Uani 1 1 d . . . . .
H19A H 0.6376 0.4329 0.2999 0.043 Uiso 1 1 calc R U . . .
H19B H 0.5788 0.4096 0.2432 0.043 Uiso 1 1 calc R U . . .
H19C H 0.5933 0.4541 0.3267 0.043 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
C2 O2 H2 106.4(10) . . ?
C15 N1 C16 124.85(8) . . ?
C15 N1 H1 112.1(9) . . ?
C16 N1 H1 122.9(9) . . ?
O1 C1 C2 117.58(8) . . ?
O1 C1 C6 123.21(8) . . ?
C2 C1 C6 119.22(8) . . ?
O2 C2 C3 122.63(8) . . ?
O2 C2 C1 115.98(8) . . ?
C3 C2 C1 121.34(8) . . ?
C2 C3 C4 117.40(8) . . ?
C2 C3 C7 121.45(8) . . ?
C4 C3 C7 121.14(8) . . ?
C5 C4 C3 124.91(8) . . ?
C5 C4 H4A 117.5 . . ?
C3 C4 H4A 117.5 . . ?
C4 C5 C6 117.13(8) . . ?
C4 C5 C11 120.24(8) . . ?
C6 C5 C11 122.63(8) . . ?
C15 C6 C1 116.68(8) . . ?
C15 C6 C5 123.63(8) . . ?
C1 C6 C5 119.68(8) . . ?
C3 C7 C10 109.69(8) . . ?
C3 C7 C9 112.49(8) . . ?
C10 C7 C9 107.84(8) . . ?
C3 C7 C8 109.26(8) . . ?
C10 C7 C8 110.13(8) . . ?
C9 C7 C8 107.39(8) . . ?
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 105.81(8) . . ?
C14 C11 C5 111.78(8) . . ?
C12 C11 C5 110.14(8) . . ?
C14 C11 C13 105.64(8) . . ?
C12 C11 C13 111.38(8) . . ?
C5 C11 C13 111.86(8) . . ?
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 123.04(8) . . ?
N1 C15 H15A 118.5 . . ?
C6 C15 H15A 118.5 . . ?
N1 C16 C17 106.02(8) . . ?
N1 C16 C19 109.90(8) . . ?
C17 C16 C19 110.98(10) . . ?
N1 C16 C18 108.74(9) . . ?
C17 C16 C18 110.23(10) . . ?
C19 C16 C18 110.84(9) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
O1 C1 1.3000(11) . ?
O2 C2 1.3658(11) . ?
O2 H2 0.884(16) . ?
N1 C15 1.3022(12) . ?
N1 C16 1.4824(12) . ?
N1 H1 0.939(16) . ?
C1 C2 1.4286(13) . ?
C1 C6 1.4331(12) . ?
C2 C3 1.3765(13) . ?
C3 C4 1.4253(13) . ?
C3 C7 1.5357(13) . ?
C4 C5 1.3727(14) . ?
C4 H4A 0.9500 . ?
C5 C6 1.4425(13) . ?
C5 C11 1.5424(12) . ?
C6 C15 1.4234(13) . ?
C7 C10 1.5360(14) . ?
C7 C9 1.5367(13) . ?
C7 C8 1.5431(14) . ?
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 1.5385(13) . ?
C11 C12 1.5423(14) . ?
C11 C13 1.5448(14) . ?
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 C17 1.5217(15) . ?
C16 C19 1.5256(15) . ?
C16 C18 1.5273(16) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
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 0.884(16) 2.116(15) 2.6312(10) 116.4(12) .
N1 H1 O1 0.939(16) 1.682(16) 2.5013(10) 143.6(14) .
O2 H2 O1 0.884(16) 2.044(16) 2.8076(10) 144.0(13) 13_665
