Computational screening for prediction of co-crystals: method comparison and experimental validation
Molajafari, Fateme; Li, Tianrui; Abbasichaleshtori, Mehrnaz; Hajian Z. D., Moein; Cozzolino, Anthony F.; Fandrick, Daniel R.; Howe, Joshua D.; CrystEngComm 26 (2024) 1620–1636; doi:10.1039/D3CE01252B

data_7248219
_publ_section_title
;
 Computational screening for prediction of co-crystals: method comparison
 and experimental validation
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              1620
_journal_page_last               1636
_journal_paper_doi               10.1039/D3CE01252B
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         '2(C8 H10 N4 O2), 3(C6 H6 O3), 2.5(H2 O)'
_chemical_formula_sum            'C34 H43 N8 O15.5'
_chemical_formula_weight         811.76
_chemical_melting_point          379.83
_chemical_name_common            Caff-Py
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-09
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-10-04 deposited with the CCDC.	2024-02-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.97060(16)
_cell_length_b                   26.3924(3)
_cell_length_c                   19.9773(3)
_cell_measurement_reflns_used    14440
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.3230
_cell_measurement_theta_min      3.3440
_cell_volume                     7365.98(16)
_computing_cell_refinement       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 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
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_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   -121.00 -35.00   0.50    1.00    --  -47.13 -21.00 -48.00  172
  2  \w    -39.00  28.00   0.50    1.00    --  -47.13  21.00 117.00  134
  3  \w   -162.00 -86.00   0.50    4.00    --  -91.75-104.00 176.00  152
  4  \w   -162.00 -74.00   0.50    4.00    --  -91.75-127.00  98.00  176
  5  \w     43.00 109.00   0.50    4.00    --  113.25-127.00  98.00  132
  6  \w    101.00 178.00   0.50    4.00    --  113.25  21.00 117.00  154
  7  \w     86.00 122.00   0.50    4.00    --  113.25-143.00 -71.00   72
  8  \w    -65.00 -39.00   0.50    1.00    --  -47.11 127.00 174.00   52
  9  \w    -26.00  24.00   0.50    1.00    --   47.11 -19.00-150.00  100
 10  \w     44.00  69.00   0.50    4.00    --  113.25 -61.00 -60.00   50
 11  \w     61.00  94.00   0.50    4.00    --  113.25 -77.00 150.00   66
 12  \w     42.00  68.00   0.50    4.00    --  113.25 -77.00-120.00   52
 13  \w    118.00 174.00   0.50    4.00    --  113.25  45.00-180.00  112
 14  \w     49.00  93.00   0.50    4.00    --  113.25 -77.00  60.00   88
 15  \w     47.00 104.00   0.50    4.00    --  113.25-125.00-180.00  114
 16  \w     43.00  69.00   0.50    4.00    --  113.25 -61.00 -30.00   52
 17  \w     43.00  68.00   0.50    4.00    --  113.25 -61.00 150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0248992000
_diffrn_orient_matrix_UB_12      -0.0381868000
_diffrn_orient_matrix_UB_13      0.0557078000
_diffrn_orient_matrix_UB_21      -0.0170320000
_diffrn_orient_matrix_UB_22      -0.0412984000
_diffrn_orient_matrix_UB_23      -0.0531335000
_diffrn_orient_matrix_UB_31      0.1060899000
_diffrn_orient_matrix_UB_32      -0.0155579000
_diffrn_orient_matrix_UB_33      0.0044984000
_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  0.0475
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            41596
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.452
_diffrn_reflns_theta_min         3.349
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.997
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.99a (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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_description       plate
_exptl_crystal_F_000             3416
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_size_max          0.137
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     581
_refine_ls_number_reflns         7897
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0560P)^2^+3.7611P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1203
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6403
_reflns_number_total             7897
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce01252b3.cif
_cod_data_source_block           agi923a
_cod_depositor_comments          'Adding full bibliography for 7248219.cif.'
_cod_original_cell_volume        7365.95(15)
_cod_original_formula_sum        'C34 H43 N8 O15.50'
_cod_database_code               7248219
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C25H20N4O6F2
_chemical_oxdiff_usercomment     'AGI   CAF-PYr--sc  A'
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.875
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3D(H3D), C3E(H3E), C4A(H4A), C5A(H5A), C6A(H6A), C4B(H4B), C5B(H5B),
 C6B(H6B), C4C(H4C), C5C(H5C), C6C(H6C)
2.b Idealised Me refined as rotating group:
 C6D(H6DA,H6DB,H6DC), C7D(H7DA,H7DB,H7DC), C8D(H8DA,H8DB,H8DC), C6E(H6EA,H6EB,
 H6EC), C7E(H7EA,H7EB,H7EC), C8E(H8EA,H8EB,H8EC)
;
_shelx_res_checksum              73361
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id 'AGI   CAF-PYr--sc  A'
_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 1.221
_oxdiff_exptl_absorpt_empirical_full_min 0.841