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_2300760
_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
_audit_creation_date             2024-11-08
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2024.11.02 svn.r19aeb66f for OlexSys, GUI svn.r7078)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.4765(2)
_cell_length_b                   9.1539(1)
_cell_length_c                   23.3338(4)
_cell_measurement_reflns_used    14663
_cell_measurement_temperature    99.97(11)
_cell_measurement_theta_max      76.0860
_cell_measurement_theta_min      4.3480
_cell_volume                     3092.11(8)
_computing_cell_refinement       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 4.2047
_diffrn_detector_type            TitanS2
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.9970
_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   -114.00 -21.00   1.00   60.00    --  -44.42 -53.00-160.00   93
  2  \w     21.00 114.00   1.00   60.00    --   44.42  53.00 -16.00   93
  3  \w     85.00 177.00   1.00  150.00    --  108.00  53.00 -16.00   92
  4  \w     39.00 131.00   1.00  150.00    --  108.00 -53.00-160.00   92
  5  \w   -114.00 -20.00   1.00   60.00    --  -44.42 -57.00 120.00   94
  6  \w    -68.00  25.00   1.00   60.00    --  -44.42  53.00 -16.00   93
  7  \w    -87.00  -6.00   1.00   60.00    --  -44.42 125.00  60.00   81
  8  \w   -114.00 -20.00   1.00   60.00    --  -44.42 -57.00-180.00   94
  9  \w   -114.00 -20.00   1.00   60.00    --  -44.42 -57.00   0.00   94
 10  \w   -113.00 -22.00   1.00   60.00    --  -44.42 -44.00-116.14   91
 11  \w   -115.00 -22.00   1.00   60.00    --  -44.42 -37.00  60.00   93
 12  \w     13.00  42.00   1.00   60.00    --   44.42  80.00-112.78   29
 13  \w     13.00  42.00   1.00   60.00    --   44.42  79.00  10.25   29
 14  \w     13.00  42.00   1.00   60.00    --   44.42  79.00 -45.91   29
 15  \w     13.00  42.00   1.00   60.00    --   44.42  81.00  31.62   29
 16  \w     14.00  42.00   1.00   60.00    --   44.42  77.00 123.81   28
 17  \w    -21.00  75.00   1.00   60.00    --   44.42 -77.00  60.00   96
 18  \w    -25.00  68.00   1.00   60.00    --   44.42 -53.00-160.00   93
 19  \w     13.00  42.00   1.00   60.00    --   44.42  82.00 169.00   29
 20  \w     80.00 177.00   1.00  150.00    --  108.00  69.00-175.39   97
 21  \w     80.00 178.00   1.00  150.00    --  108.00  70.00 -30.20   98
 22  \w     82.00 177.00   1.00  150.00    --  108.00  64.00  73.41   95
 23  \w     83.00 177.00   1.00  150.00    --  108.00  59.00-109.08   94
 24  \w     81.00 177.00   1.00  150.00    --  108.00  68.00 156.17   96
 25  \w     82.00 177.00   1.00  150.00    --  108.00  64.00 136.03   95
 26  \w     83.00 177.00   1.00  150.00    --  108.00  61.00   0.00   94
 27  \w     80.00 177.00   1.00  150.00    --  108.00  69.00 -90.00   97
 28  \w     39.00 133.00   1.00  150.00    --  108.00 -61.00   0.00   94
 29  \w     83.00 177.00   1.00  150.00    --  108.00  61.00 -90.00   94
 30  \w     36.00 138.00   1.00  150.00    --  108.00 -77.00   0.00  102
 31  \w     27.00 107.00   1.00  150.00    --  108.00 -94.00 -30.00   80
 32  \w     83.00 177.00   1.00  150.00    --  108.00  61.00  60.00   94
 33  \w     85.00 177.00   1.00  150.00    --  108.00  54.00 -37.58   92
 34  \w     82.00 177.00   1.00  150.00    --  108.00  62.00  50.44   95
 35  \w     83.00 177.00   1.00  150.00    --  108.00  61.00-180.00   94
 36  \w     80.00 178.00   1.00  150.00    --  108.00  71.00 -24.13   98
 37  \w     83.00 177.00   1.00  150.00    --  108.00  61.00  90.00   94
 38  \w     83.00 177.00   1.00  150.00    --  108.00  61.00-150.00   94
 39  \w     83.00 177.00   1.00  150.00    --  108.00  61.00-143.73   94
 40  \w     83.00 177.00   1.00  150.00    --  108.00  59.00 -98.06   94
 41  \w     27.00 107.00   1.00  150.00    --  108.00 -94.00-120.00   80
 42  \w     81.00 177.00   1.00  150.00    --  108.00  67.00  29.45   96
 43  \w     84.00 177.00   1.00  150.00    --  108.00  56.00  13.57   93
 44  \w     83.00 177.00   1.00  150.00    --  108.00  61.00 -30.00   94
 45  \w     27.00 107.00   1.00  150.00    --  108.00 -94.00   0.00   80
 46  \w     83.00 177.00   1.00  150.00    --  108.00  61.00 120.00   94
 47  \w     81.00 176.00   1.00  150.00    --  108.00  66.00-132.93   95
 48  \w     80.00 178.00   1.00  150.00    --  108.00  71.00   5.70   98
 49  \w     83.00 177.00   1.00  150.00    --  108.00  59.00 108.96   94
 50  \w     81.00 176.00   1.00  150.00    --  108.00  66.00  17.67   95
 51  \w     38.00 112.00   1.00  150.00    --  108.00-125.00 120.00   74
 52  \w     82.00  83.00   1.00  150.00    --  108.00  62.00 131.79    1
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dualflex, TitanS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0851385000
_diffrn_orient_matrix_UB_12      0.0704091000
_diffrn_orient_matrix_UB_13      -0.0027942000
_diffrn_orient_matrix_UB_21      -0.0271839000
_diffrn_orient_matrix_UB_22      0.0933791000
_diffrn_orient_matrix_UB_23      0.0439807000
_diffrn_orient_matrix_UB_31      0.0355073000
_diffrn_orient_matrix_UB_32      -0.0971794000
_diffrn_orient_matrix_UB_33      0.0402454000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\b'
_diffrn_radiation_wavelength     1.39222
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.9996
_diffrn_reflns_Laue_measured_fraction_max 0.9970
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4385
_diffrn_reflns_point_group_measured_fraction_full 0.9996
_diffrn_reflns_point_group_measured_fraction_max 0.9970
_diffrn_reflns_theta_full        56.6504
_diffrn_reflns_theta_max         76.18
_diffrn_reflns_theta_min         4.39
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.447
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.490
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.96a (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    1.437
_exptl_crystal_description       block
_exptl_crystal_F_000             1397.831
_exptl_crystal_size_max          0.238
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.113
_refine_diff_density_max         0.3623
_refine_diff_density_min         -0.3323
_refine_diff_density_rms         0.0746
_refine_ls_d_res_high            0.7169
_refine_ls_d_res_low             9.0840
_refine_ls_goodness_of_fit_ref   1.0682
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4385
_refine_ls_number_restraints     534
_refine_ls_restrained_S_all      1.0039
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0558P)^2^+1.8120P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1000
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              20
_reflns_limit_h_min              0
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              32
_reflns_limit_l_min              0
_reflns_number_gt                4228
_reflns_number_total             4385
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            pl5048.cif
_cod_data_source_block           WYlid_Large6_Cub_100K_fm2
_cod_depositor_comments
'Adding full bibliography for 2300759--2300765.cif.'
_cod_database_code               2300760
_chemical_oxdiff_formula         'C20 H14 O3 S'
_chemical_oxdiff_usercomment     ZA_Meurer
_diffrn_oxdiff_digest_hkl
;
014131ac26328ff14d86c85ffc964c30a65578
;
_olex2_refinement_description
;
1. Rigid body (RIGU) restrains
 C9, S1, C3, C1, C2, C11, C4, O1, O3, C20, C12, C10, C5, C19, C13, C6, C14,
 C18, O2, C8, C7, C15, C17, C16
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C18, S1, C3, C1, C2, C11, C4, H1a, H1b, H1c, H2a, H2b, H2c, O1, O3, C20, C12,
 C10, C5, C19, C13, C9, C6, C14, O2, C8, H9, C7, H6, C15, C17, H18, H8, H7, C16,
  H15, H17, H16
 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:      Toluene
   DATE:           2024-10-17_13-37-43
;
_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.464
_oxdiff_exptl_absorpt_empirical_full_min 0.594