High-throughput encapsulated nanodroplet screening for accelerated co-crystal discovery
Metherall, Jessica P.; Corner, Philip A.; McCabe, James F.; Probert, Michael R.; Hall, Michael J.; Chemical Science 16 (2025) 9843–9853; doi:10.1039/D4SC07556K

data_1574439
_publ_section_title
;
 High-throughput encapsulated nanodroplet screening for accelerated
 co-crystal discovery
;
_journal_issue                   22
_journal_name_full               'Chemical Science'
_journal_page_first              9843
_journal_page_last               9853
_journal_paper_doi               10.1039/D4SC07556K
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C7 H4 N2 O6, 0.5(C10 H8 N2)'
_chemical_formula_sum            'C12 H8 N3 O6'
_chemical_formula_weight         290.21
_chemical_name_systematic        '4,4'-bipyridine_3,5-dinitrobenzoic acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2kmb8t
_audit_creation_date             2025-02-26
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2025-03-04 deposited with the CCDC.	2025-04-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.411(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2329(7)
_cell_length_b                   22.008(3)
_cell_length_c                   9.4129(11)
_cell_measurement_reflns_used    2086
_cell_measurement_temperature    294.98(17)
_cell_measurement_theta_max      67.6890
_cell_measurement_theta_min      4.0050
_cell_volume                     1273.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.98(17)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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    -71.00 -46.00   0.50   14.00    --  -43.94 131.00 -33.00   50
  2  \w    -61.00 -23.00   0.50   14.00    --  -43.94 139.00 141.00   76
  3  \w     56.00  81.00   0.50   14.00    --   44.81-131.00-104.00   50
  4  \w     75.00 100.00   0.50   14.00    --   44.81-139.00  81.00   50
  5  \w   -108.00 -83.00   0.50   56.00    --  -88.13-139.00  81.00   50
  6  \w   -145.00 -93.00   0.50   56.00    --  -88.13-131.00-104.00  104
  7  \w   -143.00-114.00   0.50   56.00    --  -88.13-139.00  81.00   58
  8  \w    -71.00 -46.00   0.50   56.00    --  -88.13 131.00 -33.00   50
  9  \w    138.00 163.00   0.50   56.00    --  100.88 131.00 -33.00   50
 10  \w     46.00  71.00   0.50   56.00    --  100.88-131.00-104.00   50
 11  \w    108.00 133.00   0.50   56.00    --  100.88 139.00 141.00   50
 12  \w    108.00 133.00   0.50   56.00    --  109.87 139.00 141.00   50
 13  \w    113.00 138.00   0.50   56.00    --  109.87 131.00 -33.00   50
 14  \w     52.00  77.00   0.50   56.00    --  109.87-139.00  81.00   50
 15  \w     46.00  71.00   0.50   56.00    --  109.87-131.00-104.00   50
 16  \w    -10.00  36.00   0.50   14.00    --  -43.94  38.00 -60.00   92
 17  \w     -9.00  32.00   0.50   14.00    --  -43.94  38.00 -90.00   82
 18  \w    -14.00  35.00   0.50   14.00    --  -43.94  38.00  60.00   98
 19  \w    -10.00  30.00   0.50   14.00    --  -43.94  38.00 -30.00   80
 20  \w   -130.00 -46.00   0.50   56.00    --  -88.13 -15.00-150.00  168
 21  \w   -156.00-123.00   0.50   56.00    --  -88.13 -77.00-180.00   66
 22  \w     25.00  53.00   0.50   56.00    --  100.88 -61.00 150.00   56
 23  \w     91.00 134.00   0.50   56.00    --  100.88  30.00 150.00   86
 24  \w     49.00  93.00   0.50   56.00    --  100.88 -95.00 -90.00   88
 25  \w     25.00  54.00   0.50   56.00    --  100.88 -61.00 -30.00   58
 26  \w     25.00  54.00   0.50   56.00    --  100.88 -61.00 -60.00   58
 27  \w    143.00 171.00   0.50   56.00    --  100.88  30.00 150.00   56
 28  \w     76.00 101.00   0.50   56.00    --  100.88-139.00  81.00   50
 29  \w    127.00 178.00   0.50   56.00    --  109.87  77.00   0.00  102
 30  \w    127.00 176.00   0.50   56.00    --  109.87  77.00-120.00   98
 31  \w     64.00  93.00   0.50   56.00    --  109.87 -95.00-120.00   58
 32  \w     44.00  93.00   0.50   56.00    --  109.87 -95.00 -60.00   98
 33  \w     63.00  93.00   0.50   56.00    --  109.87 -95.00   0.00   60
 34  \w     68.00  93.00   0.50   56.00    --  109.87 -95.00 -30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0229758000
_diffrn_orient_matrix_UB_12      -0.0253265000
_diffrn_orient_matrix_UB_13      -0.1542343000
_diffrn_orient_matrix_UB_21      -0.0175031000
_diffrn_orient_matrix_UB_22      0.0652271000
_diffrn_orient_matrix_UB_23      -0.0601312000
_diffrn_orient_matrix_UB_31      0.2489954000
_diffrn_orient_matrix_UB_32      0.0022817000
_diffrn_orient_matrix_UB_33      0.0087171000
_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  0.0387
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8471
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.595
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_min         4.017
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_description       plate
_exptl_crystal_F_000             596
_exptl_crystal_preparation
;
Crystallised from a saturated solution of 4,4'-bipyridine, 
3,5-dinitrobenzoic acid (2:1) in MeOH.
;
_exptl_crystal_recrystallization_method
'High-throughput screening via the ENaCt protocol using SPT Labtech mosquito.'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.023
_exptl_crystal_size_min          0.017
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2234
_refine_ls_number_restraints     145
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0593
_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^)+(0.0704P)^2^+0.3127P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1570
_refine_ls_wR_factor_ref         0.1716
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1578
_reflns_number_total             2234
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07556k2.cif
_cod_data_source_block           3,5-dinitrobenzoic_acid_4,4-bipyridine_k
_cod_depositor_comments
'Adding full bibliography for 1574434--1574463.cif.'
_cod_original_cell_volume        1273.9(3)
_cod_database_code               1574439
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.731
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
2. Restrained distances
 H6A-O6A
 0.9 with sigma of 0.02
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C6A(H6Aa), C4A(H4A), C5B(H5B), C2B(H2B), C4B(H4B), C3B(H3B)
;
_shelx_res_checksum              24858
_shelx_hkl_checksum              34781
_olex2_exptl_crystal_mounting_method
'Crystal mounted using inert oil from the encapsulation crystallisation technique onto a MiTeGen Kapton micromount.'
_olex2_submission_original_sample_id '4,4'-bipyridine_3,5-dinitrobenzoic acid'
_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 1.473
_oxdiff_exptl_absorpt_empirical_full_min 0.694