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_1574463
_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         'C3 H3 O, C10 H8 N2'
_chemical_formula_sum            'C13 H11 N2 O'
_chemical_formula_weight         211.24
_chemical_name_systematic        4,4'-bipyridine_quinol
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2kmbcx
_audit_creation_date             2024-07-15
_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                112.063(6)
_cell_angle_beta                 109.788(6)
_cell_angle_gamma                94.584(5)
_cell_formula_units_Z            2
_cell_length_a                   7.8241(4)
_cell_length_b                   8.6299(5)
_cell_length_c                   9.2154(6)
_cell_measurement_reflns_used    3023
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      75.9940
_cell_measurement_theta_min      5.5860
_cell_volume                     527.10(7)
_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 0.997
_diffrn_measured_fraction_theta_max 0.908
_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     48.00 104.00   0.50    0.60    --  108.19 -77.00  90.00  112
  2  \w     26.00  54.00   0.50    0.60    --   96.68 -61.00 150.00   56
  3  \w     20.00  49.00   0.50    0.60    --   96.68 -45.00  60.00   58
  4  \w     46.00 103.00   0.50    0.60    --  108.19 -77.00   0.00  114
  5  \w     17.00  49.00   0.50    0.60    --   96.68 -45.00 -60.00   64
  6  \w     19.00  51.00   0.50    0.60    --   96.68 -45.00-150.00   64
  7  \w     45.00  75.00   0.50    0.60    --  108.19 -77.00-180.00   60
  8  \w     93.00 118.00   0.50    0.60    --  108.19-134.00-179.00   50
  9  \w     40.00  66.00   0.50    0.60    --   48.00-134.00-179.00   52
 10  \w     63.00  89.00   0.50    0.60    --   96.68-136.00   1.00   52
 11  \w    -27.00  32.00   0.50    0.60    --  -48.75  19.00-180.00  118
 12  \w      3.00  30.00   0.50    0.60    --  -48.75  19.00 -90.00   54
 13  \w    -24.00   1.00   0.50    0.60    --  -48.75  19.00 -90.00   50
 14  \w    -48.00 -14.00   0.50    0.60    --  -92.21  45.00 -60.00   68
 15  \w    -45.00 -13.00   0.50    0.60    --  -92.21  45.00 120.00   64
 16  \w     72.00 117.00   0.50    0.60    --   48.00 136.00  65.00   90
 17  \w     97.00 177.00   0.50    0.60    --  108.19  45.00 150.00  160
 18  \w     72.00 109.00   0.50    0.60    --   48.00 134.00-112.00   74
 19  \w     76.00 120.00   0.50    0.60    --   48.00 125.00-180.00   88
 20  \w     75.00 101.00   0.50    0.60    --   48.00 125.00-120.00   52
 21  \w     82.00 119.00   0.50    0.60    --   96.68 136.00  65.00   74
 22  \w     68.00 123.00   0.50    0.60    --  108.19 134.00-112.00  110
 23  \w     24.00  65.00   0.50    0.60    --   48.00 -57.00-120.00   82
 24  \w    -29.00  -1.00   0.50    0.60    --   48.00 -57.00-120.00   56
 25  \w   -101.00 -70.00   0.50    0.60    --  -92.21 -61.00  30.00   62
 26  \w   -130.00-105.00   0.50    0.60    --  -92.21-136.00   1.00   50
 27  \w   -168.00 -84.00   0.50    0.60    --  -92.21 -61.00  60.00  168
 28  \w   -160.00-119.00   0.50    0.60    --  -92.21 -61.00  30.00   82
 29  \w    -67.00 -29.00   0.50    0.60    --  -92.21 125.00 -60.00   76
 30  \w    -90.00 -65.00   0.50    0.60    --  -48.75 134.00-112.00   50
 31  \w   -111.00 -61.00   0.50    0.60    --  -92.21 125.00-150.00  100
 32  \w    -47.00 -19.00   0.50    0.60    --  -92.21 125.00-150.00   56
 33  \w    -90.00 -64.00   0.50    0.60    --  -92.21 134.00-112.00   52
 34  \w   -112.00 -71.00   0.50    0.60    --  -92.21 125.00 -60.00   82
 35  \w    -90.00 -65.00   0.50    0.60    --  -48.75 136.00  65.00   50
 36  \w   -120.00 -62.00   0.50    0.60    --  -92.21 136.00  65.00  116
;
_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      0.1280871000
_diffrn_orient_matrix_UB_12      -0.0098848000
_diffrn_orient_matrix_UB_13      0.1636658000
_diffrn_orient_matrix_UB_21      -0.0338997000
_diffrn_orient_matrix_UB_22      0.1702626000
_diffrn_orient_matrix_UB_23      0.1091126000
_diffrn_orient_matrix_UB_31      -0.1698502000
_diffrn_orient_matrix_UB_32      -0.1011545000
_diffrn_orient_matrix_UB_33      0.0021121000
_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  0.0238
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5155
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.804
_diffrn_reflns_theta_min         5.649
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.693
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82258
_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    1.331
_exptl_crystal_description       plate
_exptl_crystal_F_000             222
_exptl_crystal_preparation
;
Crystallised from a saturated solution of 4,4'-bipyridine
and quinol (1:1) in 1,4-dioxane.
;
_exptl_crystal_recrystallization_method
'High-throughput screening via the ENaCt protocol using SPT Labtech mosquito.'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.081
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2042
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0636P)^2^+0.0903P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1137
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1810
_reflns_number_total             2042
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07556k2.cif
_cod_data_source_block           44-bipyridine_quinol
_cod_depositor_comments
'Adding full bibliography for 1574434--1574463.cif.'
_cod_original_cell_volume        527.10(6)
_cod_database_code               1574463
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C12 H10 O2 N6'
_shelx_estimated_absorpt_t_max   0.946
_shelx_estimated_absorpt_t_min   0.685
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
2. 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
3.a Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C2B(H2B), C3A(H3A), C3B(H3B), C4A(H4A), C5A(H5A), C7A(H7A),
 C8A(H8A), C9A(H9A), C10A(H10A)
;
_shelx_res_checksum              72009
_shelx_hkl_checksum              54271
_olex2_exptl_crystal_mounting_method
'Crystal mounted using inert oil from the encapsulation crystallisation technique onto a Mitegan Kapton micromount.'
_olex2_submission_original_sample_id 4,4'-bipyridine_quinol
_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 1.575
_oxdiff_exptl_absorpt_empirical_full_min 0.591