9,10-Anthraquinones Disubstituted with Linear Alkoxy Groups: Spectroscopy, Electrochemistry, and Peculiarities of Their 2D and 3D Supramolecular Organizations.
Maranda-Niedbała, Agnieszka; Krzyżewska, Klaudyna; Kotwica, Kamil; Skórka, Łukasz; Drapała, Jakub; Jarzembska, Katarzyna N.; Zagórska, Małgorzata; Proń, Adam; Nowakowski, Robert; Langmuir : the ACS journal of surfaces and colloids  (2020) –; doi:10.1021/acs.langmuir.0c02586

data_4518287
_publ_section_title
;
 9,10-Anthraquinones Disubstituted with Linear Alkoxy Groups:
 Spectroscopy, Electrochemistry, and Peculiarities of Their 2D and 3D
 Supramolecular Organizations.
;
_journal_name_full
'Langmuir : the ACS journal of surfaces and colloids'
_journal_paper_doi               10.1021/acs.langmuir.0c02586
_journal_year                    2020
_chemical_formula_moiety         'C26 H32 O4'
_chemical_formula_sum            'C26 H32 O4'
_chemical_formula_weight         408.51
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                82.122(3)
_cell_angle_beta                 93.736(4)
_cell_angle_gamma                94.110(3)
_cell_formula_units_Z            1
_cell_length_a                   14.5145(6)
_cell_length_b                   8.2297(3)
_cell_length_c                   4.6059(2)
_cell_measurement_reflns_used    6103
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.2360
_cell_measurement_theta_min      3.0330
_cell_volume                     542.73(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.55a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.55a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.55a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2687
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -115.00 -12.00   1.00    1.00    --  -42.68 -77.00 150.00  103
  2  \w    -96.00 -12.00   1.00    1.00    --  -42.68 125.00-120.00   84
  3  \w     21.00 113.00   1.00    1.00    --   42.68  38.00-180.00   92
  4  \w     32.00  81.00   1.00    1.00    --   42.68 -99.00-120.00   49
  5  \w    -28.00  64.00   1.00    1.00    --   42.68 -38.00   0.00   92
  6  \w     57.00 149.00   1.00    1.00    --  109.50  15.00  60.00   92
  7  \w     57.00 149.00   1.00    1.00    --  109.50  15.00 150.00   92
  8  \w     40.00 136.00   1.00    1.00    --  109.50 -61.00  30.00   96
  9  \w     40.00 133.00   1.00    1.00    --  109.50 -45.00-150.00   93
 10  \w     30.00 106.00   1.00    1.00    --  109.50 -94.00  30.00   76
 11  \w     54.00 112.00   1.00    1.00    --  109.50-125.00 -90.00   58
 12  \w     30.00 106.00   1.00    1.00    --  109.50 -94.00 150.00   76
 13  \w     86.00 149.00   1.00    1.00    --  109.50  30.00-150.00   63
 14  \w     54.00 112.00   1.00    1.00    --  109.50-125.00  30.00   58
 15  \w     40.00 133.00   1.00    1.00    --  109.50 -45.00 120.00   93
 16  \w     40.00 133.00   1.00    1.00    --  109.50 -45.00 -90.00   93
 17  \w     86.00 149.00   1.00    1.00    --  109.50  45.00  60.00   63
 18  \w     54.00 112.00   1.00    1.00    --  109.50-125.00 -30.00   58
 19  \w   -113.00 -17.00   1.00    1.00    --  -42.68 -57.00  30.00   96
 20  \w     32.00  81.00   1.00    1.00    --   42.68 -99.00 150.00   49
 21  \w     17.00 113.00   1.00    1.00    --   42.68  57.00 -30.00   96
 22  \w     21.00 113.00   1.00    1.00    --   42.68  38.00 -60.00   92
 23  \w     12.00 115.00   1.00    1.00    --   42.68  77.00   0.00  103
 24  \w     86.00 149.00   1.00    1.00    --  109.50  45.00-120.00   63
 25  \w     83.00 149.00   1.00    1.00    --  109.50  61.00 120.00   66
 26  \w     86.00 149.00   1.00    1.00    --  109.50  30.00 -60.00   63
 27  \w     83.00 149.00   1.00    1.00    --  109.50  61.00   0.00   66
 28  \w     79.00 149.00   1.00    1.00    --  109.50  77.00-120.00   70
 29  \w     83.00 149.00   1.00    1.00    --  109.50  61.00 150.00   66
 30  \w     83.00 149.00   1.00    1.00    --  109.50  61.00-150.00   66
 31  \w     79.00 149.00   1.00    1.00    --  109.50  77.00 -90.00   70
 32  \w     83.00 149.00   1.00    1.00    --  109.50  61.00  30.00   66
 33  \w     79.00 149.00   1.00    1.00    --  109.50  77.00 -60.00   70
 34  \w   -115.00 -12.00   1.00    1.00    --  -42.68 -77.00-150.00  103
 35  \w     32.00  81.00   1.00    1.00    --   42.68 -99.00  90.00   49
 36  \w    -28.00  64.00   1.00    1.00    --   42.68 -38.00 120.00   92
 37  \w     12.00 115.00   1.00    1.00    --   42.68  77.00  90.00  103
 38  \w     12.00 115.00   1.00    1.00    --   42.68  77.00-180.00  103
 39  \w     83.00 149.00   1.00    1.00    --  109.50  61.00  90.00   66
 40  \w     79.00 149.00   1.00    1.00    --  109.50  77.00   0.00   70
 41  \w     79.00 149.00   1.00    1.00    --  109.50  77.00 -30.00   70
 42  \w     83.00 149.00   1.00    1.00    --  109.50  61.00  60.00   66
 43  \w     83.00 149.00   1.00    1.00    --  109.50  61.00-120.00   66
 44  \w     86.00 149.00   1.00    1.00    --  109.50  45.00-150.00   63
 45  \w     79.00 149.00   1.00    1.00    --  109.50  77.00  30.00   70
 46  \w     79.00 149.00   1.00    1.00    --  109.50  77.00  90.00   70
 47  \w     79.00 149.00   1.00    1.00    --  109.50  77.00 120.00   70
 48  \w     79.00 149.00   1.00    1.00    --  109.50  77.00 150.00   70
 49  \w     17.00 113.00   1.00    1.00    --   42.68  57.00  60.00   96
 50  \w     21.00 113.00   1.00    1.00    --   42.68  38.00 -30.00   92
 51  \w    -42.00 128.00   1.00    1.00    --   42.68   0.00-180.00  170
 52  \w    -42.00 128.00   1.00    1.00    --   42.68   0.00-150.00  170
 53  \w     12.00 115.00   1.00    1.00    --   42.68  77.00 -30.00  103
 54  \w     83.00 149.00   1.00    1.00    --  109.50  61.00 -90.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1047907261
_diffrn_orient_matrix_UB_12      0.0136915392
_diffrn_orient_matrix_UB_13      0.0162057339
_diffrn_orient_matrix_UB_21      0.0194047820
_diffrn_orient_matrix_UB_22      0.1306865097
_diffrn_orient_matrix_UB_23      0.2095516417
_diffrn_orient_matrix_UB_31      0.0013191748
_diffrn_orient_matrix_UB_32      0.1363487277
_diffrn_orient_matrix_UB_33      -0.2649507876
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            12452
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.755
_diffrn_reflns_theta_min         3.057
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.659
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.390
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.55a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_description       plate
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.399
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2239
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0569
_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/[\s^2^(Fo^2^)+(0.0952P)^2^+0.1091P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1555
_refine_ls_wR_factor_ref         0.1752
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1769
_reflns_number_total             2239
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            2019_11_03_JD_AntOC6_100K_02_CCDC2004140.cif
_cod_data_source_block           2019_11_03_jd_antoc6_100k_02
_cod_database_code               4518287
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C26 H32 O4'
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.779
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C10(H10A,H10B), C8(H8A,H8B), C9(H9A,H9B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C5(H5)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              93421
_shelx_hkl_checksum              65687
_olex2_date_sample_data_collection 2019-11-03
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.215
_oxdiff_exptl_absorpt_empirical_full_min 0.364