#------------------------------------------------------------------------------
#$Date: 2020-12-05 02:40:14 +0200 (Sat, 05 Dec 2020) $
#$Revision: 259550 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/82/4518290.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_4518290
loop_
_publ_author_name
'Maranda-Niedbała, Agnieszka'
'Krzyżewska, Klaudyna'
'Kotwica, Kamil'
'Skórka, Łukasz'
'Drapała, Jakub'
'Jarzembska, Katarzyna N.'
'Zagórska, Małgorzata'
'Proń, Adam'
'Nowakowski, Robert'
_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         'C30 H40 O4'
_chemical_formula_sum            'C30 H40 O4'
_chemical_formula_weight         464.62
_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                81.744(4)
_cell_angle_beta                 93.137(3)
_cell_angle_gamma                90.740(3)
_cell_formula_units_Z            1
_cell_length_a                   16.9493(6)
_cell_length_b                   8.1949(4)
_cell_length_c                   4.6048(2)
_cell_measurement_reflns_used    9673
_cell_measurement_temperature    94.9(2)
_cell_measurement_theta_max      76.0600
_cell_measurement_theta_min      5.1650
_cell_volume                     632.01(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 0.988
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -113.00 -54.00   1.00    1.00    --  -42.68-152.00  73.00   59
  2  ω    -26.00  68.00   1.00    1.00    --   42.68 -57.00-180.00   94
  3  ω    -26.00  68.00   1.00    1.00    --   42.68 -57.00 -60.00   94
  4  ω     32.00  81.00   1.00    1.00    --   42.68 -99.00-150.00   49
  5  ω     17.00 113.00   1.00    1.00    --   42.68  57.00  90.00   96
  6  ω     79.00 149.00   1.00    1.00    --  109.50  77.00 -90.00   70
  7  ω     30.00 106.00   1.00    1.00    --  109.50 -94.00-120.00   76
  8  ω     30.00 106.00   1.00    1.00    --  109.50 -94.00 120.00   76
  9  ω     30.00 106.00   1.00    1.00    --  109.50 -94.00 -30.00   76
 10  ω     40.00 133.00   1.00    1.00    --  109.50 -45.00 -30.00   93
 11  ω     54.00 112.00   1.00    1.00    --  109.50-125.00  90.00   58
 12  ω     30.00 106.00   1.00    1.00    --  109.50 -94.00 150.00   76
 13  ω     86.00 149.00   1.00    1.00    --  109.50  30.00  90.00   63
 14  ω     40.00 133.00   1.00    1.00    --  109.50 -45.00-150.00   93
 15  ω     37.00 132.00   1.00    1.00    --  109.50 -30.00  90.00   95
 16  ω     86.00 149.00   1.00    1.00    --  109.50  30.00  30.00   63
 17  ω     31.00 149.00   1.00    1.00    --  109.50 -15.00-180.00  118
 18  ω     12.00 115.00   1.00    1.00    --   42.68  77.00  90.00  103
 19  ω    -26.00  68.00   1.00    1.00    --   42.68 -57.00  60.00   94
 20  ω     21.00 113.00   1.00    1.00    --   42.68  38.00 -90.00   92
 21  ω     12.00 115.00   1.00    1.00    --   42.68  77.00-180.00  103
 22  ω     17.00 113.00   1.00    1.00    --   42.68  57.00   0.00   96
 23  ω     79.00 149.00   1.00    1.00    --  109.50  77.00 150.00   70
 24  ω     79.00 149.00   1.00    1.00    --  109.50  77.00 120.00   70
 25  ω     86.00 149.00   1.00    1.00    --  109.50  45.00-150.00   63
 26  ω     83.00 149.00   1.00    1.00    --  109.50  61.00  30.00   66
 27  ω     86.00 149.00   1.00    1.00    --  109.50  45.00 120.00   63
 28  ω     83.00 149.00   1.00    1.00    --  109.50  61.00-120.00   66
 29  ω     83.00 149.00   1.00    1.00    --  109.50  61.00-150.00   66
 30  ω     79.00 149.00   1.00    1.00    --  109.50  77.00 -30.00   70
 31  ω     79.00 149.00   1.00    1.00    --  109.50  77.00  60.00   70
 32  ω     86.00 149.00   1.00    1.00    --  109.50  45.00 -30.00   63
 33  ω   -113.00 -17.00   1.00    1.00    --  -42.68 -57.00-120.00   96
 34  ω     12.00 115.00   1.00    1.00    --   42.68  77.00   0.00  103
 35  ω     17.00 113.00   1.00    1.00    --   42.68  57.00 -30.00   96
 36  ω     12.00 115.00   1.00    1.00    --   42.68  77.00  30.00  103
 37  ω     12.00 115.00   1.00    1.00    --   42.68  77.00 -90.00  103
 38  ω     79.00 149.00   1.00    1.00    --  109.50  77.00   0.00   70
 39  ω     79.00 149.00   1.00    1.00    --  109.50  77.00-120.00   70
 40  ω     83.00 149.00   1.00    1.00    --  109.50  61.00 -90.00   66
 41  ω     79.00 149.00   1.00    1.00    --  109.50  77.00-150.00   70
 42  ω     79.00 149.00   1.00    1.00    --  109.50  77.00 -60.00   70
 43  ω     83.00 149.00   1.00    1.00    --  109.50  61.00 150.00   66
 44  ω     79.00 149.00   1.00    1.00    --  109.50  77.00  30.00   70
 45  ω     83.00 149.00   1.00    1.00    --  109.50  61.00 120.00   66
 46  ω     83.00 149.00   1.00    1.00    --  109.50  61.00   0.00   66
 47  ω     83.00 149.00   1.00    1.00    --  109.50  61.00-180.00   66
 48  ω    -42.00 128.00   1.00    1.00    --   42.68   0.00 -60.00  170
 49  ω    -42.00 128.00   1.00    1.00    --   42.68   0.00 -90.00  170
 50  ω    -42.00 128.00   1.00    1.00    --   42.68   0.00-180.00  170
 51  ω    -42.00 128.00   1.00    1.00    --   42.68   0.00-120.00  170
 52  ω    -42.00 128.00   1.00    1.00    --   42.68   0.00-150.00  170
 53  ω     83.00 149.00   1.00    1.00    --  109.50  61.00  90.00   66
 54  ω     83.00 149.00   1.00    1.00    --  109.50  61.00 -60.00   66
 55  ω     79.00 149.00   1.00    1.00    --  109.50  77.00-180.00   70
 56  ω     86.00 149.00   1.00    1.00    --  109.50  45.00  90.00   63
 57  ω     86.00 149.00   1.00    1.00    --  109.50  45.00 -90.00   63
 58  ω     83.00 149.00   1.00    1.00    --  109.50  61.00  60.00   66
 59  ω     30.00 106.00   1.00    1.00    --  109.50 -94.00   0.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0105518470
_diffrn_orient_matrix_UB_12      0.0880374994
_diffrn_orient_matrix_UB_13      0.2736372803
_diffrn_orient_matrix_UB_21      -0.0899095773
_diffrn_orient_matrix_UB_22      0.0270114867
_diffrn_orient_matrix_UB_23      -0.0073733146
_diffrn_orient_matrix_UB_31      -0.0095586064
_diffrn_orient_matrix_UB_32      -0.1661473578
_diffrn_orient_matrix_UB_33      0.1991918644
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_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            18326
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.380
_diffrn_reflns_theta_min         2.611
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.623
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.336
_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    1.221
_exptl_crystal_description       plate
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.554
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2579
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0506
_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)+(0.0979P)²+0.1281P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1608
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2176
_reflns_number_total             2579
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            2019_10_31_JD_AntOC8_95K_01_CCDC2004143.cif
_cod_data_source_block           2019_10_31_jd_antoc8_95k_01
_cod_database_code               4518290
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C30 H40 O4'
_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.
;
_reflns_odcompleteness_completeness 98.79
_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:
 C10(H10A,H10B), C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C13(H13A,H13B),
 C12(H12A,H12B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_olex2_date_sample_data_collection 2019-10-31
_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 3.635
_oxdiff_exptl_absorpt_empirical_full_min 0.264
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
O2 O 0.18327(5) 0.28549(12) 0.6803(2) 0.0193(3) Uani 1 1 d . . . . .
O1 O -0.05164(5) 0.31328(12) -0.0725(2) 0.0211(3) Uani 1 1 d . . . . .
C7 C 0.06757(7) -0.04511(16) 0.1995(3) 0.0147(3) Uani 1 1 d . . . . .
C3 C 0.07649(7) 0.23246(16) 0.3301(3) 0.0161(3) Uani 1 1 d . . . . .
H3 H 0.057400 0.339567 0.310876 0.019 Uiso 1 1 calc R . . . .
C1 C -0.02871(7) 0.17018(16) -0.0369(3) 0.0157(3) Uani 1 1 d . . . . .
C4 C 0.14166(7) 0.18493(17) 0.5182(3) 0.0168(3) Uani 1 1 d . . . . .
C2 C 0.03989(7) 0.11657(16) 0.1694(3) 0.0150(3) Uani 1 1 d . . . . .
C5 C 0.16956(8) 0.02288(17) 0.5492(3) 0.0178(3) Uani 1 1 d . . . . .
H5 H 0.212964 -0.008559 0.676363 0.021 Uiso 1 1 calc R . . . .
C6 C 0.13278(8) -0.09022(17) 0.3914(3) 0.0178(3) Uani 1 1 d . . . . .
H6 H 0.151627 -0.197598 0.413169 0.021 Uiso 1 1 calc R . . . .
C10 C 0.29219(7) 0.57698(17) 0.6804(3) 0.0175(3) Uani 1 1 d . . . . .
H10A H 0.310207 0.477608 0.613266 0.021 Uiso 1 1 calc R . . . .
H10B H 0.278710 0.656437 0.508133 0.021 Uiso 1 1 calc R . . . .
C8 C 0.15460(7) 0.45040(16) 0.6825(3) 0.0170(3) Uani 1 1 d . . . . .
H8A H 0.104878 0.447377 0.777939 0.020 Uiso 1 1 calc R . . . .
H8B H 0.146667 0.507479 0.483563 0.020 Uiso 1 1 calc R . . . .
C9 C 0.21796(7) 0.53624(17) 0.8525(3) 0.0174(3) Uani 1 1 d . . . . .
H9A H 0.232366 0.465854 1.035096 0.021 Uiso 1 1 calc R . . . .
H9B H 0.196563 0.637472 0.901486 0.021 Uiso 1 1 calc R . . . .
C11 C 0.35950(7) 0.64679(18) 0.8600(3) 0.0191(3) Uani 1 1 d . . . . .
H11A H 0.374964 0.565103 1.026633 0.023 Uiso 1 1 calc R . . . .
H11B H 0.340780 0.743017 0.935514 0.023 Uiso 1 1 calc R . . . .
C13 C 0.50161(7) 0.75493(18) 0.8617(3) 0.0196(3) Uani 1 1 d . . . . .
H13A H 0.516993 0.667812 1.019512 0.024 Uiso 1 1 calc R . . . .
H13B H 0.485115 0.848604 0.950096 0.024 Uiso 1 1 calc R . . . .
C12 C 0.43176(7) 0.69523(17) 0.6814(3) 0.0192(3) Uani 1 1 d . . . . .
H12A H 0.448143 0.600769 0.594968 0.023 Uiso 1 1 calc R . . . .
H12B H 0.416890 0.781874 0.522044 0.023 Uiso 1 1 calc R . . . .
C14 C 0.57326(8) 0.80515(19) 0.6810(3) 0.0231(3) Uani 1 1 d . . . . .
H14A H 0.589652 0.711751 0.591603 0.028 Uiso 1 1 calc R . . . .
H14B H 0.558066 0.892888 0.523986 0.028 Uiso 1 1 calc R . . . .
C15 C 0.64295(8) 0.8636(2) 0.8636(4) 0.0279(4) Uani 1 1 d . . . . .
H15A H 0.686380 0.892102 0.740393 0.042 Uiso 1 1 calc GR . . . .
H15B H 0.658649 0.776976 1.018420 0.042 Uiso 1 1 calc GR . . . .
H15C H 0.627711 0.958538 0.947093 0.042 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-11 -1 0 0.0270
-1 4 -1 0.1758
11 1 0 0.0270
1 -4 1 0.1758
-1 -5 0 0.0478
2 2 -2 0.1913
-2 0 3 0.3169
1 -3 -3 0.2006
0 5 0 0.0996
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
C4 O2 C8 118.59(10) . . ?
C2 C7 C1 121.68(12) . 2 ?
C6 C7 C1 119.32(12) . 2 ?
C6 C7 C2 118.99(12) . . ?
C4 C3 C2 119.09(12) . . ?
O1 C1 C7 121.25(12) . 2 ?
O1 C1 C2 121.04(12) . . ?
C7 C1 C2 117.70(12) 2 . ?
O2 C4 C3 124.93(12) . . ?
O2 C4 C5 114.83(12) . . ?
C3 C4 C5 120.24(12) . . ?
C7 C2 C3 120.86(13) . . ?
C7 C2 C1 120.58(12) . . ?
C3 C2 C1 118.56(12) . . ?
C6 C5 C4 120.13(13) . . ?
C5 C6 C7 120.69(13) . . ?
C11 C10 C9 113.28(10) . . ?
O2 C8 C9 105.75(10) . . ?
C8 C9 C10 112.74(10) . . ?
C10 C11 C12 112.83(10) . . ?
C12 C13 C14 113.35(11) . . ?
C13 C12 C11 113.65(11) . . ?
C15 C14 C13 112.94(12) . . ?
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
O2 C4 1.3559(15) . ?
O2 C8 1.4436(16) . ?
O1 C1 1.2259(16) . ?
C7 C1 1.4811(17) 2 ?
C7 C2 1.3968(19) . ?
C7 C6 1.3962(19) . ?
C3 C4 1.3898(19) . ?
C3 C2 1.4037(17) . ?
C1 C2 1.4898(19) . ?
C4 C5 1.401(2) . ?
C5 C6 1.3800(18) . ?
C10 C9 1.5315(17) . ?
C10 C11 1.5259(16) . ?
C8 C9 1.5192(16) . ?
C11 C12 1.5289(17) . ?
C13 C12 1.5245(17) . ?
C13 C14 1.5284(18) . ?
C14 C15 1.5247(19) . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-10.8619 -0.7658 0.0133 -0.1784 0.9558 0.2337
-0.7651 4.2076 -1.4499 -0.0344 0.1931 -0.9806
10.8619 0.7658 -0.0133 0.1784 -0.9558 -0.2337
0.7651 -4.2076 1.4499 0.0344 -0.1931 0.9806
-0.5627 -5.2781 -0.1007 -0.4982 -0.0912 0.8623
1.8350 2.3684 -2.4315 -0.4375 -0.0831 -0.8954
-1.8387 0.4711 2.9654 0.8335 0.1562 0.5300
1.3864 -2.8896 -2.7070 -0.9805 -0.1827 -0.0724
-0.1027 5.3001 0.1758 0.5136 0.1511 -0.8446
