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_4518288
_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         'C22 H24 O4'
_chemical_formula_sum            'C22 H24 O4'
_chemical_formula_weight         352.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-10-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.810(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.1860(4)
_cell_length_b                   7.2626(5)
_cell_length_c                   15.1791(8)
_cell_measurement_reflns_used    4553
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.9630
_cell_measurement_theta_min      5.6790
_cell_volume                     883.32(9)
_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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2687
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_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    -73.00  30.00   1.00    1.00    --  -42.68  77.00-180.00  103
  2  \w   -113.00 -17.00   1.00    1.00    --  -42.68 -57.00  30.00   96
  3  \w     17.00 113.00   1.00    1.00    --   42.68  57.00 -60.00   96
  4  \w     57.00 149.00   1.00    3.13    --  109.50  15.00 -60.00   92
  5  \w     54.00 112.00   1.00    3.13    --  109.50-125.00 120.00   58
  6  \w     86.00 149.00   1.00    3.13    --  109.50  45.00  30.00   63
  7  \w     54.00 112.00   1.00    3.13    --  109.50-125.00 -90.00   58
  8  \w     57.00 149.00   1.00    3.13    --  109.50  15.00-180.00   92
  9  \w     40.00 136.00   1.00    3.13    --  109.50 -61.00  90.00   96
 10  \w     37.00 132.00   1.00    3.13    --  109.50 -30.00-150.00   95
 11  \w    -64.00  28.00   1.00    1.00    --  -42.68  38.00 -30.00   92
 12  \w    -68.00  27.00   1.00    1.00    --  -42.68  57.00  60.00   95
 13  \w     12.00 115.00   1.00    1.00    --   42.68  77.00 150.00  103
 14  \w     83.00 149.00   1.00    3.13    --  109.50  61.00  60.00   66
 15  \w     79.00 149.00   1.00    3.13    --  109.50  77.00-180.00   70
 16  \w     40.00 136.00   1.00    3.13    --  109.50 -61.00 -60.00   96
 17  \w     79.00 149.00   1.00    3.13    --  109.50  77.00 -30.00   70
 18  \w     79.00 149.00   1.00    3.13    --  109.50  77.00 -90.00   70
 19  \w     86.00 149.00   1.00    3.13    --  109.50  45.00 -30.00   63
 20  \w     12.00 115.00   1.00    1.00    --   42.68  77.00  90.00  103
 21  \w     12.00 115.00   1.00    1.00    --   42.68  77.00-120.00  103
 22  \w     12.00 115.00   1.00    1.00    --   42.68  77.00   0.00  103
 23  \w     79.00 130.00   1.00    3.13    --  109.50  77.00  30.00   51
 24  \w     79.00 149.00   1.00    3.13    --  109.50  77.00-120.00   70
 25  \w     54.00 112.00   1.00    3.13    --  109.50-125.00 -30.00   58
;
_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      0.1918828000
_diffrn_orient_matrix_UB_12      -0.0130860000
_diffrn_orient_matrix_UB_13      0.0227372000
_diffrn_orient_matrix_UB_21      0.0079920000
_diffrn_orient_matrix_UB_22      0.1061132000
_diffrn_orient_matrix_UB_23      -0.0869009000
_diffrn_orient_matrix_UB_31      0.0083562000
_diffrn_orient_matrix_UB_32      0.1832233000
_diffrn_orient_matrix_UB_33      0.0518621000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0947
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10309
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.130
_diffrn_reflns_theta_min         5.712
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.643
_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    1.325
_exptl_crystal_description       needle
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.475
_exptl_crystal_size_mid          0.251
_exptl_crystal_size_min          0.126
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0819
_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^)+(0.1747P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2133
_refine_ls_wR_factor_ref         0.2335
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1459
_reflns_number_total             1826
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            2019_10_28_JD_AntOC4_100K_01_CCDC2004139.cif
_cod_data_source_block           2019_10_28_jd_antoc4_100k_01
_cod_database_code               4518288
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 H24 O4'
_reflns_odcompleteness_completeness 100.00
_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:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              54327
_shelx_hkl_checksum              10407
_olex2_date_sample_data_collection 2019-10-28
_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 4.270
_oxdiff_exptl_absorpt_empirical_full_min 0.262