Synthesis and quantum crystallographic evaluation of WYLID: YLID's red rival
Meurer, Florian; Schimpf, Maximilian; Hischa, Birgit; Hennig, Christoph; Rehbein, Julia; Kleemiss, Florian; Bodensteiner, Michael; Journal of Applied Crystallography 58 (2025) 678–687; doi:10.1107/S160057672500175X

data_2300759
_publ_section_title
;
 Synthesis and quantum crystallographic evaluation of WYLID: YLID's red
 rival
;
_journal_coeditor_code           PL5048
_journal_issue                   3
_journal_name_full               'Journal of Applied Crystallography'
_journal_page_first              678
_journal_page_last               687
_journal_paper_doi               10.1107/S160057672500175X
_journal_volume                  58
_journal_year                    2025
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H10 O3'
_chemical_formula_sum            'C18 H10 O3'
_chemical_formula_weight         274.278
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_symmetry_Int_Tables_number      43
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-29
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            32
_cell_length_a                   18.0174(1)
_cell_length_b                   20.9221(2)
_cell_length_c                   26.0847(2)
_cell_measurement_reflns_used    73652
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.6990
_cell_measurement_theta_min      3.3130
_cell_volume                     9832.94(13)
_computing_cell_refinement       'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.131a 64-bit (release 19-07-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.9942
_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     43.00  74.00   0.50    6.00    --   34.00  65.00  63.30   62
  2  \w     45.00  76.00   0.50    6.00    --   38.00  71.00 109.52   62
  3  \w     57.00  88.00   0.50    6.00    --   50.00  70.00   1.60   62
  4  \w     60.00  91.00   0.50    6.00    --   54.00  72.00-158.57   62
  5  \w     61.00  92.00   0.50    6.00    --   54.00  70.00 145.27   62
  6  \w     60.00  91.00   0.50    6.00    --   54.00  72.00-123.76   62
  7  \w   -103.00 -71.00   0.50    6.00    --  -62.00 -62.00  81.91   64
  8  \w     71.00 103.00   0.50    6.00    --   62.00  63.00  27.02   64
  9  \w    -90.00 -22.00   0.50    6.00    --  -63.83 125.00  90.00  136
 10  \w   -109.00 -76.00   0.50    6.00    --  -66.00 -56.00-178.09   66
 11  \w   -108.00 -76.00   0.50    6.00    --  -66.00 -57.00 -73.25   64
 12  \w   -110.00 -79.00   0.50    6.00    --  -70.00 -64.00  53.63   62
 13  \w   -113.00 -80.00   0.50    6.00    --  -70.00 -55.00-104.10   66
 14  \w   -100.00 -32.00   0.50    6.00    --  -73.70 125.00-180.00  136
 15  \w   -100.00 -32.00   0.50    6.00    --  -73.70 125.00 -90.00  136
 16  \w   -115.00 -83.00   0.50    6.00    --  -74.00 -63.00 127.56   64
 17  \w   -120.00 -86.00   0.50    6.00    --  -74.00 -42.00 149.07   68
 18  \w     38.00  84.00   0.50    6.00    --   75.50 -95.00 150.00   92
 19  \w     38.00  84.00   0.50    6.00    --   75.50 -95.00  90.00   92
 20  \w     34.00 102.00   0.50    6.00    --   75.50-125.00 -30.00  136
 21  \w     34.00 102.00   0.50    6.00    --   75.50-125.00-120.00  136
 22  \w     38.00  84.00   0.50    6.00    --   75.50 -95.00-120.00   92
 23  \w     44.00 121.00   0.50    6.00    --   75.50  15.00 120.00  154
 24  \w     39.00 113.00   0.50    6.00    --   75.94   0.00-150.00  148
 25  \w     34.00 103.00   0.50    6.00    --   75.94-125.00   0.00  138
 26  \w   -118.00 -73.00   0.50    6.00    --  -76.64-125.00-120.00   90
 27  \w   -112.00 -36.00   0.50    6.00    --  -78.25 135.00  56.56  152
 28  \w   -123.00 -40.00   0.50    6.00    --  -78.25 152.00 -25.09  166
 29  \w   -112.00 -36.00   0.50    6.00    --  -78.25 135.00  56.56  152
 30  \w   -123.00 -40.00   0.50    6.00    --  -78.25 152.00 -25.09  166
 31  \w   -123.00 -89.00   0.50    6.00    --  -78.25 -46.00 -93.39   68
 32  \w   -112.00 -36.00   0.50    6.00    --  -78.25 135.00 -69.88  152
 33  \w   -121.00 -89.00   0.50    6.00    --  -78.25 -55.00  72.94   64
 34  \w   -116.00 -37.00   0.50    6.00    --  -78.25 141.00 -40.70  158
 35  \w    -74.00 -42.00   0.50    6.00    --  -78.25  75.00 -65.25   64
 36  \w   -107.00 -36.00   0.50    6.00    --  -78.25 127.00-103.24  142
 37  \w   -121.00 -89.00   0.50    6.00    --  -78.25 -55.00 -37.38   64
 38  \w    -74.00 -43.00   0.50    6.00    --  -78.25  76.00  56.17   62
 39  \w   -107.00 -36.00   0.50    6.00    --  -78.25 127.00-103.24  142
 40  \w     90.00 127.00   0.50    6.00    --   79.75  36.00  34.29   74
 41  \w     68.00 127.00   0.50    6.00    --   79.75  24.00 -88.79  118
 42  \w     39.00 101.00   0.50    6.00    --   79.75-116.00-152.30  124
 43  \w     90.00 127.00   0.50    6.00    --   79.75  36.00 123.88   74
 44  \w     37.00 110.00   0.50    6.00    --   79.75-129.00 -56.06  146
 45  \w     72.00 127.00   0.50    6.00    --   79.75  25.00-160.60  110
 46  \w    -19.00   7.00   0.50    6.00    --   -6.00 103.00  32.70   52
 47  \w      3.00  34.00   0.50    6.00    --   10.00  93.00-119.98   62
 48  \w      6.00  34.00   0.50    6.00    --   14.00  94.00 131.32   56
 49  \w     27.00  59.00   0.50    6.00    --   22.00  74.00  -8.47   64
 50  \w     17.00  43.00   0.50    6.00    --   22.00  90.00 161.11   52
 51  \w     34.00  66.00   0.50    6.00    --   30.00  76.00  16.31   64
 52  \w     33.00  65.00   0.50    6.00    --   30.00  77.00 -73.11   64
 53  \w     51.00  83.00   0.50    6.00    --   42.00  63.00 -30.85   64
 54  \w     47.00  79.00   0.50    6.00    --   42.00  74.00-179.83   64
 55  \w   -111.00 -36.00   0.50    6.00    --  -73.70   0.00-150.00  150
 56  \w   -111.00 -36.00   0.50    6.00    --  -73.70   0.00 -90.00  150
 57  \w   -114.00 -82.00   0.50    6.00    --  -74.00 -65.00 -14.05   64
 58  \w     39.00 113.00   0.50    6.00    --   75.94   0.00  30.00  148
 59  \w   -118.00 -73.00   0.50    6.00    --  -76.64-125.00 150.00   90
 60  \w   -118.00 -73.00   0.50    6.00    --  -76.64-125.00  90.00   90
 61  \w   -103.00 -35.00   0.50    6.00    --  -76.64 125.00 -30.00  136
 62  \w   -113.00 -79.00   0.50    6.00    --  -78.00 -80.00-109.35   68
 63  \w   -117.00 -86.00   0.50    6.00    --  -78.25 -68.00   8.46   62
 64  \w   -118.00 -86.00   0.50    6.00    --  -78.25 -66.00  93.98   64
 65  \w   -113.00 -80.00   0.50    6.00    --  -78.25 -79.00-154.82   66
 66  \w   -121.00 -89.00   0.50    6.00    --  -78.25 -55.00 -15.14   64
 67  \w   -120.00 -88.00   0.50    6.00    --  -78.25 -59.00 136.81   64
 68  \w   -120.00 -88.00   0.50    6.00    --  -78.25 -60.00-141.39   64
 69  \w   -107.00 -36.00   0.50    6.00    --  -78.25 127.00 164.97  142
 70  \w   -116.00 -85.00   0.50    6.00    --  -78.25 -71.00-100.32   62
 71  \w   -113.00 -80.00   0.50    6.00    --  -78.25 -80.00  62.87   66
 72  \w   -113.00 -80.00   0.50    6.00    --  -78.25 -79.00 179.54   66
 73  \w   -119.00 -87.00   0.50    6.00    --  -78.25 -62.00 -38.07   64
 74  \w   -119.00 -87.00   0.50    6.00    --  -78.25 -62.00  72.23   64
 75  \w   -119.00 -87.00   0.50    6.00    --  -78.25 -62.00 -78.28   64
 76  \w   -115.00 -37.00   0.50    6.00    --  -78.25 139.00  19.56  156
 77  \w   -120.00 -88.00   0.50    6.00    --  -78.25 -60.00-155.34   64
 78  \w   -121.00 -89.00   0.50    6.00    --  -78.25 -55.00 144.87   64
 79  \w   -120.00 -88.00   0.50    6.00    --  -78.25 -59.00 -53.09   64
 80  \w   -113.00 -81.00   0.50    6.00    --  -78.25 -78.00  38.43   64
 81  \w   -113.00 -81.00   0.50    6.00    --  -78.25 -78.00 129.65   64
 82  \w      2.00  29.00   0.50    6.00    --   10.00  96.00  52.58   54
 83  \w    -25.00   2.00   0.50    6.00    --  -10.00 106.00-140.20   54
 84  \w     13.00  42.00   0.50    6.00    --   18.00  91.00-109.45   58
 85  \w     39.00  70.00   0.50    6.00    --   34.00  75.00-151.03   62
 86  \w     45.00  76.00   0.50    6.00    --   38.00  71.00 -66.90   62
 87  \w     45.00  76.00   0.50    6.00    --   38.00  71.00-120.14   62
 88  \w     43.00  75.00   0.50    6.00    --   38.00  74.00 125.60   64
 89  \w     53.00  84.00   0.50    6.00    --   46.00  71.00  59.95   62
 90  \w     57.00  88.00   0.50    6.00    --   50.00  71.00  24.86   62
 91  \w     60.00  91.00   0.50    6.00    --   54.00  72.00 177.27   62
 92  \w     64.00  95.00   0.50    6.00    --   58.00  72.00 -37.69   62
 93  \w     25.00  71.00   0.50    6.00    --   62.96 -95.00  60.00   92
 94  \w     38.00  84.00   0.50    6.00    --   75.50 -95.00 120.00   92
 95  \w   -118.00 -73.00   0.50    6.00    --  -76.64-125.00 -60.00   90
 96  \w   -103.00 -35.00   0.50    6.00    --  -76.64 125.00  90.00  136
 97  \w   -115.00 -83.00   0.50    6.00    --  -78.25 -74.00 140.84   64
 98  \w   -123.00 -40.00   0.50    6.00    --  -78.25 151.00  90.02  166
 99  \w   -121.00 -88.00   0.50    6.00    --  -78.25 -56.00 -76.92   66
100  \w   -120.00 -88.00   0.50    6.00    --  -78.25 -60.00-160.59   64
101  \w   -120.00 -88.00   0.50    6.00    --  -78.25 -58.00  29.45   64
102  \w   -120.00 -87.00   0.50    6.00    --  -78.25 -61.00 -99.33   66
103  \w    -69.00 -37.00   0.50    6.00    --  -78.25  62.00 -36.72   64
104  \w     68.00 127.00   0.50    6.00    --   79.75  24.00  27.35  118
105  \w     48.00 124.00   0.50    6.00    --   79.75  13.00 127.21  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0657137000
_diffrn_orient_matrix_UB_12      -0.0184846000
_diffrn_orient_matrix_UB_13      -0.0346841000
_diffrn_orient_matrix_UB_21      -0.0360353000
_diffrn_orient_matrix_UB_22      -0.0656029000
_diffrn_orient_matrix_UB_23      -0.0098976000
_diffrn_orient_matrix_UB_31      -0.0411866000
_diffrn_orient_matrix_UB_32      0.0278225000
_diffrn_orient_matrix_UB_33      -0.0467717000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_Laue_measured_fraction_full 0.9996
_diffrn_reflns_Laue_measured_fraction_max 0.9942
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            5026
_diffrn_reflns_point_group_measured_fraction_full 0.9996
_diffrn_reflns_point_group_measured_fraction_max 0.9884
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         75.32
_diffrn_reflns_theta_min         3.65
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.826
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.93a (Rigaku Oxford Diffraction, 2023)
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 green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_description       block
_exptl_crystal_F_000             4560.097
_exptl_crystal_size_max          0.087
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.0968
_refine_diff_density_min         -0.0924
_refine_diff_density_rms         0.0178
_refine_ls_abs_structure_details
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_d_res_high            0.7969
_refine_ls_d_res_low             12.0960
_refine_ls_goodness_of_fit_ref   1.0550
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     559
_refine_ls_number_reflns         5026
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0550
_refine_ls_R_factor_all          0.0163
_refine_ls_R_factor_gt           0.0161
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0108P)^2^+5.3369P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0366
_refine_ls_wR_factor_ref         0.0366
_reflns_Friedel_coverage         0.982
_reflns_limit_h_max              22
_reflns_limit_h_min              -22
_reflns_limit_k_max              26
_reflns_limit_k_min              -26
_reflns_limit_l_max              31
_reflns_limit_l_min              -32
_reflns_number_gt                4962
_reflns_number_total             5026
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            pl5048.cif
_cod_data_source_block           Biindandione_DW_CuKa_100K
_cod_depositor_comments
'Adding full bibliography for 2300759--2300765.cif.'
_cod_original_sg_symbol_Hall     ' F 2 -2d'
_cod_database_code               2300759
_chemical_oxdiff_formula         C18O3H23
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
;
_olex2_refine_details
;
Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field by employing cluster charges
or modelled using implicit solvation models, depending on the software used.
The following options were used:
   SOFTWARE:       ORCA 5.0
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         R2SCAN
   BASIS SET:      def2-TZVP
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2024-10-29_14-21-30
;
_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 1.916
_oxdiff_exptl_absorpt_empirical_full_min 0.654