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_2300762
_publ_section_title
;
 Synthesis and quantum crystallographic evaluation of WYLID: YLID's red
 rival
;
_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_formula_moiety         'C20 H14 O3 S'
_chemical_formula_sum            'C20 H14 O3 S'
_chemical_formula_weight         334.398
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_Int_Tables_number      61
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-23
_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            8
_cell_length_a                   14.49062(7)
_cell_length_b                   9.15691(4)
_cell_length_c                   23.32900(11)
_cell_measurement_reflns_used    243270
_cell_measurement_temperature    100.00(18)
_cell_measurement_theta_max      51.4760
_cell_measurement_theta_min      2.2260
_cell_volume                     3095.51(2)
_computing_cell_refinement       'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.91a 64-bit (release 29-09-2023))'
_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(18)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9998
_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    -79.00 -26.00   0.50   20.00    --  -34.48 151.00  77.00  106
  2  \w    -60.00 -11.00   0.50   20.00    --  -34.48 123.00 -83.00   98
  3  \w     32.00  79.00   0.50   20.00    --   34.87-151.00  33.00   94
  4  \w     32.00  82.00   0.50   20.00    --   37.72-151.00  33.00  100
  5  \w    -64.00 -11.00   0.50   20.00    --  -38.11 123.00 -83.00  106
  6  \w    -82.00 -26.00   0.50   20.00    --  -38.11 151.00  77.00  112
  7  \w      6.00  37.00   0.50   20.00    --    0.00  72.00  13.57   62
  8  \w      2.00  35.00   0.50   20.00    --    0.00  79.00 130.45   66
  9  \w      3.00  35.00   0.50   20.00    --    0.00  78.00  65.24   64
 10  \w      6.00  37.00   0.50   20.00    --    0.00  72.00 101.03   62
 11  \w      0.00  35.00   0.50   20.00    --    0.00  83.00-132.96   70
 12  \w     -1.00  31.00   0.50   20.00    --   -4.00  78.00 -14.73   64
 13  \w      8.00  41.00   0.50   20.00    --   -4.00  49.00-175.57   66
 14  \w      2.00  39.00   0.50   20.00    --    4.00  85.00-166.02   74
 15  \w    -14.00  29.00   0.50   20.00    --   -8.00  92.00 -71.41   86
 16  \w    -52.00 -23.00   0.50   20.00    --  -12.00 145.00  38.53   58
 17  \w      8.00  34.00   0.50   20.00    --   16.00  94.00-116.12   52
 18  \w      8.00  34.00   0.50   20.00    --   16.00  94.00  -4.53   52
 19  \w     15.00  43.00   0.50   20.00    --   20.00  90.00 -76.30   56
 20  \w     14.00  41.00   0.50   20.00    --   20.00  92.00  90.93   54
 21  \w     15.00  42.00   0.50   20.00    --   20.00  91.00  12.78   54
 22  \w     15.00  42.00   0.50   20.00    --   20.00  91.00 168.79   54
 23  \w    -53.00 -14.00   0.50   20.00    --  -24.00 127.00 150.66   78
 24  \w     28.00  60.00   0.50   20.00    --   24.00  76.00 -93.59   64
 25  \w     28.00  60.00   0.50   20.00    --   24.00  76.00  65.12   64
 26  \w     31.00  63.00   0.50   20.00    --   28.00  77.00 163.38   64
 27  \w    -79.00 -29.00   0.50   20.00    --  -32.00 156.00 -35.57  100
 28  \w     35.00  67.00   0.50   20.00    --   32.00  77.00 -89.67   64
 29  \w     35.00  67.00   0.50   20.00    --   32.00  77.00-133.42   64
 30  \w     38.00  69.00   0.50   20.00    --   32.00  72.00 -39.57   62
 31  \w    -61.00 -13.00   0.50   20.00    --  -34.48 125.00-150.00   96
 32  \w     -2.00  72.00   0.50   20.00    --   34.87   0.00 150.00  148
 33  \w    -71.00 -19.00   0.50   20.00    --  -36.00 137.00  11.81  104
 34  \w     39.00  71.00   0.50   20.00    --   36.00  77.00 -44.49   64
 35  \w     39.00  71.00   0.50   20.00    --   36.00  77.00  83.93   64
 36  \w    -82.00 -49.00   0.50   20.00    --  -36.30 -41.00   3.03   66
 37  \w    -83.00 -46.00   0.50   20.00    --  -36.30 -36.00-151.52   74
 38  \w    -83.00 -47.00   0.50   20.00    --  -36.30 -37.00 -62.05   72
 39  \w    -83.00 -47.00   0.50   20.00    --  -36.30 -37.00 -83.95   72
 40  \w    -29.00   7.00   0.50   20.00    --  -36.30  10.00 143.29   72
 41  \w    -72.00 -40.00   0.50   20.00    --  -36.30 -76.00-170.54   64
 42  \w    -73.00 -20.00   0.50   20.00    --  -36.30 139.00-118.99  106
 43  \w    -71.00 -40.00   0.50   20.00    --  -36.30 -77.00 166.19   62
 44  \w    -83.00 -47.00   0.50   20.00    --  -36.30 -37.00  71.63   72
 45  \w    -83.00 -49.00   0.50   20.00    --  -36.30 -38.00-171.15   68
 46  \w    -27.00   5.00   0.50   20.00    --  -36.30  60.00  79.70   64
 47  \w    -83.00 -47.00   0.50   20.00    --  -36.30 -37.00-111.48   72
 48  \w     40.00  72.00   0.50   20.00    --   36.30  77.00-100.27   64
 49  \w     40.00  72.00   0.50   20.00    --   36.30  76.00  45.93   64
 50  \w     47.00  83.00   0.50   20.00    --   36.30  37.00-140.05   72
 51  \w     40.00  72.00   0.50   20.00    --   36.30  77.00 -20.05   64
 52  \w     40.00  72.00   0.50   20.00    --   36.30  76.00 121.10   64
 53  \w     44.00  84.00   0.50   20.00    --   36.30  34.00 124.46   80
 54  \w     41.00  73.00   0.50   20.00    --   36.30  74.00  69.29   64
 55  \w     40.00  72.00   0.50   20.00    --   36.30  77.00 170.08   64
 56  \w     40.00  72.00   0.50   20.00    --   36.30  77.00 -78.02   64
 57  \w     50.00  83.00   0.50   20.00    --   36.30  40.00 142.88   66
 58  \w     45.00  84.00   0.50   20.00    --   36.30  35.00-103.49   78
 59  \w     41.00  72.00   0.50   20.00    --   36.30  75.00-114.34   62
 60  \w     40.00  72.00   0.50   20.00    --   36.30  76.00   4.59   64
 61  \w     46.00  78.00   0.50   20.00    --   36.30  59.00 176.94   64
 62  \w     40.00  72.00   0.50   20.00    --   36.30  76.00 102.15   64
 63  \w     40.00  72.00   0.50   20.00    --   36.30  77.00  26.04   64
 64  \w     49.00  82.00   0.50   20.00    --   36.30  42.00  61.93   66
 65  \w    -27.00   8.00   0.50   20.00    --  -38.11  19.00 -30.00   70
 66  \w    -65.00 -13.00   0.50   20.00    --  -38.11 125.00  30.00  104
 67  \w    -65.00 -13.00   0.50   20.00    --  -38.11 125.00  60.00  104
 68  \w    -65.00 -13.00   0.50   20.00    --  -38.11 125.00-180.00  104
 69  \w    -65.00 -13.00   0.50   20.00    --  -38.11 125.00 -30.00  104
 70  \w    -65.00 -13.00   0.50   20.00    --  -38.11 125.00-120.00  104
 71  \w    -27.00   8.00   0.50   20.00    --  -38.11  19.00  30.00   70
 72  \w    -27.00   8.00   0.50   20.00    --  -38.11  19.00  60.00   70
 73  \w    -65.00 -13.00   0.50   20.00    --  -38.11 125.00 150.00  104
 74  \w    -65.00 -13.00   0.50   20.00    --  -38.11 125.00   0.00  104
 75  \w    -27.00   8.00   0.50   20.00    --  -38.11  19.00  90.00   70
 76  \w    -27.00   8.00   0.50   20.00    --  -38.11  19.00-180.00   70
 77  \w    -65.00 -13.00   0.50   20.00    --  -38.11 125.00-150.00  104
 78  \w    -27.00   8.00   0.50   20.00    --  -38.11  19.00 -60.00   70
 79  \w    -65.00 -13.00   0.50   20.00    --  -38.11 125.00 -60.00  104
 80  \w    -65.00 -13.00   0.50   20.00    --  -38.11 125.00 120.00  104
 81  \w    -65.00 -13.00   0.50   20.00    --  -38.11 125.00  90.00  104
 82  \w    -27.00   8.00   0.50   20.00    --  -38.11  19.00-120.00   70
 83  \w    -27.00   8.00   0.50   20.00    --  -38.11  19.00   0.00   70
 84  \w    -27.00   8.00   0.50   20.00    --  -38.11  19.00 150.00   70
 85  \w    -27.00   8.00   0.50   20.00    --  -38.11  19.00-150.00   70
 86  \w     33.00  64.00   0.50   20.00    --   28.00  75.00-158.75   62
 87  \w     36.00  68.00   0.50   20.00    --   32.00  76.00 -21.74   64
 88  \w    -11.00  33.00   0.50   20.00    --   34.87 -19.00 -30.00   88
 89  \w    -66.00 -15.00   0.50   20.00    --  -36.00 129.00 102.49  102
 90  \w     47.00  83.00   0.50   20.00    --   36.30  37.00 133.59   72
 91  \w     40.00  72.00   0.50   20.00    --   36.30  76.00 149.23   64
;
_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      0.0247060000
_diffrn_orient_matrix_UB_12      -0.0506593000
_diffrn_orient_matrix_UB_13      0.0171446000
_diffrn_orient_matrix_UB_21      -0.0121628000
_diffrn_orient_matrix_UB_22      0.0399442000
_diffrn_orient_matrix_UB_23      0.0249344000
_diffrn_orient_matrix_UB_31      -0.0404543000
_diffrn_orient_matrix_UB_32      -0.0429067000
_diffrn_orient_matrix_UB_33      0.0029624000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0072
_diffrn_reflns_Laue_measured_fraction_full 0.9993
_diffrn_reflns_Laue_measured_fraction_max 0.9998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            9749
_diffrn_reflns_point_group_measured_fraction_full 0.9993
_diffrn_reflns_point_group_measured_fraction_max 0.9998
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         40.25
_diffrn_reflns_theta_min         2.24
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.707
_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 red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       block
_exptl_crystal_F_000             1393.827
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.079
_refine_diff_density_max         0.1314
_refine_diff_density_min         -0.1290
_refine_diff_density_rms         0.0322
_refine_ls_d_res_high            0.5500
_refine_ls_d_res_low             9.0864
_refine_ls_goodness_of_fit_ref   1.2594
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     418
_refine_ls_number_reflns         9749
_refine_ls_number_restraints     207
_refine_ls_restrained_S_all      1.2456
_refine_ls_R_factor_all          0.0162
_refine_ls_R_factor_gt           0.0112
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0027P)^2^+0.0170P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0139
_refine_ls_wR_factor_ref         0.0142
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              26
_reflns_limit_h_min              0
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              42
_reflns_limit_l_min              0
_reflns_number_gt                8596
_reflns_number_total             9749
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            pl5048.cif
_cod_data_source_block           Ylidanhydrate_MoKaDW_cut
_cod_depositor_comments
'Adding full bibliography for 2300759--2300765.cif.'
_cod_database_code               2300762
_chemical_oxdiff_formula         'S C20 H20 O3'
_olex2_refinement_description
;
1. Rigid body (RIGU) restrains
 C20, S1, C3, C1, C2, C11, C4, C12, C10, O1, C5, C13, C9, C6, O3, C19, O2, C14,
  C8, C7, C18, C15, C17, C16
 with sigma for 1-2 distances of 0.2 and sigma for 1-3 distances of 0.2
 O2, C13
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
;
_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
   SOLVATION:      DMSO
   DATE:           2024-10-07_14-34-13
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   10658
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.431
_oxdiff_exptl_absorpt_empirical_full_min 0.857