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_1574444
_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, C10 H8 N2'
_chemical_formula_sum            'C17 H12 N4 O6'
_chemical_formula_weight         368.31
_chemical_name_systematic        '4,4'-dipyridine_3,5-dinitrobenzoic acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2kmbn6
_audit_creation_date             2024-07-16
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-07-18 deposited with the CCDC.	2025-04-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.994(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.6498(5)
_cell_length_b                   7.3982(2)
_cell_length_c                   16.4817(5)
_cell_measurement_reflns_used    6026
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      77.0540
_cell_measurement_theta_min      5.0570
_cell_volume                     1591.71(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_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      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.911
_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     35.00  69.00   0.50    0.71    --  108.00 -61.00 150.00   68
  2  \w     25.00  54.00   0.50    0.71    --   96.11 -61.00  90.00   58
  3  \w     80.00 105.00   0.50    0.71    --  108.00 -77.00  60.00   50
  4  \w     24.00  51.00   0.50    0.71    --   96.11 -45.00 120.00   54
  5  \w    -25.00  42.00   0.50    0.71    --   48.76 -38.00  90.00  134
  6  \w     25.00  67.00   0.50    0.71    --   96.11 -61.00 -60.00   84
  7  \w     39.00  65.00   0.50    0.71    --  108.00 -61.00 -90.00   52
  8  \w     38.00  97.00   0.50    0.71    --   48.76  19.00  48.00  118
  9  \w     59.00 133.00   0.50    0.71    --   96.11  19.00  48.00  148
 10  \w    116.00 143.00   0.50    0.71    --  108.00  19.00  48.00   54
 11  \w   -127.00 -13.00   0.50    0.71    --  -49.57 -19.00-119.00  228
 12  \w   -157.00 -51.00   0.50    0.71    --  -92.01 -19.00-119.00  212
 13  \w    -23.00   2.00   0.50    0.71    --  -49.57  19.00  48.00   50
 14  \w    -50.00 -15.00   0.50    0.71    --  -92.01  45.00  60.00   70
 15  \w   -104.00 -27.00   0.50    0.71    --  -92.01  77.00-120.00  154
 16  \w    -49.00 -24.00   0.50    0.71    --  -92.01  45.00-150.00   50
 17  \w    -71.00 -18.00   0.50    0.71    --  -92.01  61.00-180.00  106
 18  \w     52.00  78.00   0.50    0.71    --  108.00 -95.00-150.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix-Arc 100'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0278363000
_diffrn_orient_matrix_UB_12      0.0440429000
_diffrn_orient_matrix_UB_13      -0.0954143000
_diffrn_orient_matrix_UB_21      0.1124871000
_diffrn_orient_matrix_UB_22      -0.0298403000
_diffrn_orient_matrix_UB_23      0.0020469000
_diffrn_orient_matrix_UB_31      -0.0228286000
_diffrn_orient_matrix_UB_32      -0.2011018000
_diffrn_orient_matrix_UB_33      -0.0211435000
_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  0.0267
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9803
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.811
_diffrn_reflns_theta_min         3.386
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.018
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
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    1.537
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_preparation
;
Crystallised from a saturated solution of 4,4'-bipyridine
and 3,5-dinitrobenzoic acid (1:1) in MeNO2.
;
_exptl_crystal_recrystallization_method
'High-throughput screening via the ENaCt co-crystallisationprotocol using SPT Labtech mosquito.'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.077
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3096
_refine_ls_number_restraints     196
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0797P)^2^+0.2949P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1243
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2664
_reflns_number_total             3096
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07556k2.cif
_cod_data_source_block           44-bipyridine_35-dinitrobenzoicacid
_cod_depositor_comments
'Adding full bibliography for 1574434--1574463.cif.'
_cod_database_code               1574444
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C10 H12 O2 N4'
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.585
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
2. Restrained distances
 O6A-H6A
 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), C2B(H2B), C3B(H3B), C4A(H4A), C4B(H4B), C5B(H5B), C6A(H6AA),
 C7B(H7B), C8B(H8B), C9B(H9B), C10B(H10B)
;
_shelx_res_checksum              30449
_shelx_hkl_checksum              37556
_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 1.311
_oxdiff_exptl_absorpt_empirical_full_min 0.616