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_4518289
_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         'C38 H56 O4'
_chemical_formula_sum            'C38 H56 O4'
_chemical_formula_weight         576.82
_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             2019-11-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                81.057(3)
_cell_angle_beta                 92.570(4)
_cell_angle_gamma                86.488(4)
_cell_formula_units_Z            1
_cell_length_a                   21.8747(11)
_cell_length_b                   8.1797(3)
_cell_length_c                   4.60630(10)
_cell_measurement_reflns_used    6544
_cell_measurement_temperature    94.9(2)
_cell_measurement_theta_max      66.3320
_cell_measurement_theta_min      4.0130
_cell_volume                     811.41(5)
_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      94.9(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2687
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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    -96.00 -12.00   1.00    2.89    --  -42.68 125.00  60.00   84
  2  \w    -26.00  68.00   1.00    2.89    --   42.68 -57.00-180.00   94
  3  \w     17.00 113.00   1.00    2.89    --   42.68  57.00 -30.00   96
  4  \w     20.00 117.00   1.00    9.50    --   89.79 -61.00 -90.00   97
  5  \w     67.00 149.00   1.00    9.50    --   89.79  30.00   0.00   82
  6  \w     57.00 115.00   1.00    9.50    --   89.79-129.00 -52.00   58
  7  \w     67.00 149.00   1.00    9.50    --   89.79  30.00  30.00   82
  8  \w     24.00 106.00   1.00    9.50    --   89.79 -94.00  60.00   82
  9  \w     67.00 149.00   1.00    9.50    --   89.79  45.00 -90.00   82
 10  \w     21.00 113.00   1.00    9.50    --   89.79 -45.00 120.00   92
 11  \w     12.00 137.00   1.00    9.50    --   89.79 -15.00   0.00  125
 12  \w     54.00 112.00   1.00    9.50    --   89.79-125.00  30.00   58
 13  \w     24.00 106.00   1.00    9.50    --   89.79 -94.00 120.00   82
 14  \w     24.00 106.00   1.00    9.50    --   89.79 -94.00-150.00   82
 15  \w     67.00 149.00   1.00    9.50    --   89.79  45.00-150.00   82
 16  \w     12.00 115.00   1.00    2.89    --   42.68  77.00-150.00  103
 17  \w     17.00 113.00   1.00    2.89    --   42.68  57.00 150.00   96
 18  \w     12.00 115.00   1.00    2.89    --   42.68  77.00  60.00  103
 19  \w     59.00 149.00   1.00    9.50    --   89.79  77.00  60.00   90
 20  \w     63.00 149.00   1.00    9.50    --   89.79  61.00-180.00   86
 21  \w     59.00 149.00   1.00    9.50    --   89.79  77.00  30.00   90
 22  \w     63.00 149.00   1.00    9.50    --   89.79  61.00 150.00   86
 23  \w     63.00 149.00   1.00    9.50    --   89.79  61.00 120.00   86
 24  \w     59.00 149.00   1.00    9.50    --   89.79  77.00-150.00   90
 25  \w     59.00 149.00   1.00    9.50    --   89.79  77.00 -30.00   90
 26  \w     59.00 149.00   1.00    9.50    --   89.79  77.00 -90.00   90
 27  \w     67.00 149.00   1.00    9.50    --   89.79  30.00 120.00   82
 28  \w     12.00 115.00   1.00    2.89    --   42.68  77.00 120.00  103
 29  \w     12.00 115.00   1.00    2.89    --   42.68  77.00 -30.00  103
 30  \w     32.00  81.00   1.00    2.89    --   42.68 -99.00 -90.00   49
 31  \w     59.00 149.00   1.00    9.50    --   89.79  77.00-120.00   90
 32  \w     59.00 149.00   1.00    9.50    --   89.79  77.00 -60.00   90
 33  \w     59.00 149.00   1.00    9.50    --   89.79  77.00   0.00   90
;
_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      -0.0679501365
_diffrn_orient_matrix_UB_12      -0.0059462427
_diffrn_orient_matrix_UB_13      0.0729869156
_diffrn_orient_matrix_UB_21      0.0191172592
_diffrn_orient_matrix_UB_22      -0.0984727079
_diffrn_orient_matrix_UB_23      0.3068591230
_diffrn_orient_matrix_UB_31      0.0033284017
_diffrn_orient_matrix_UB_32      0.1636844789
_diffrn_orient_matrix_UB_33      0.1244448976
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            15665
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        66.671
_diffrn_reflns_theta_max         66.671
_diffrn_reflns_theta_min         4.056
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.575
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.401
_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    1.180
_exptl_crystal_description       plate
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.654
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2861
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.1550
_refine_ls_R_factor_gt           0.1491
_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^)+14.8179P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3545
_refine_ls_wR_factor_ref         0.3565
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2534
_reflns_number_total             2861
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            2019_11_01_JD_AntOC12_95K_01_CCDC2004141.cif
_cod_data_source_block           2019_11_01_jd_antoc12_95k_01
_cod_database_code               4518289
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C38 H56 O4'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     62.30
_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), C11(H11A,H11B), C12(H12A,H12B),
 C13(H13A,H13B), C15(H15A,H15B), C14(H14A,H14B), C18(H18A,H18B), C16(H16A,H16B),
  C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C5(H5)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              14323
_shelx_hkl_checksum              37983
_olex2_date_sample_data_collection 2019-11-01
_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 2.953
_oxdiff_exptl_absorpt_empirical_full_min 0.387