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_1574459
_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         'C8 H8 O5, 1.5(H2 O), C10 H8 N2'
_chemical_formula_sum            'C18 H19 N2 O6.5'
_chemical_formula_weight         367.35
_chemical_name_systematic        '4,4'-bipyridine_methyl gallate_H2O'
_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.cc2kmbq8
_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                99.092(2)
_cell_angle_beta                 97.390(2)
_cell_angle_gamma                105.510(2)
_cell_formula_units_Z            4
_cell_length_a                   9.5205(2)
_cell_length_b                   12.1056(3)
_cell_length_c                   16.1549(3)
_cell_measurement_reflns_used    11482
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      76.0640
_cell_measurement_theta_min      2.8000
_cell_volume                     1742.73(7)
_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      N~2~
_diffrn_ambient_temperature      149.99(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 0.992
_diffrn_measured_fraction_theta_max 0.944
_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    -36.00  -4.00   0.50    1.32    --  -43.81 109.00 101.00   64
  2  \w     32.00  77.00   0.50    1.32    --   44.81-109.00   6.00   90
  3  \w    -65.00 -40.00   0.50    1.32    --  -88.13 109.00 101.00   50
  4  \w   -144.00-111.00   0.50    1.32    --  -88.13-109.00   6.00   66
  5  \w    129.00 155.00   0.50    1.32    --  100.88 109.00 101.00   52
  6  \w     60.00  85.00   0.50    1.32    --  100.88-109.00   6.00   50
  7  \w     40.00  65.00   0.50    1.32    --  109.87-109.00   6.00   50
  8  \w    130.00 155.00   0.50    1.32    --  109.87 109.00 101.00   50
  9  \w   -121.00 -94.00   0.50    1.32    --  -43.81 -38.00 120.00   54
 10  \w    -66.00 -25.00   0.50    1.32    --  -43.81  77.00 120.00   82
 11  \w   -124.00 -91.00   0.50    1.32    --  -43.81 -38.00   0.00   66
 12  \w     -3.00  36.00   0.50    1.32    --  -43.81  38.00 150.00   78
 13  \w      0.00  28.00   0.50    1.32    --  -43.81  38.00 -30.00   56
 14  \w    -11.00  37.00   0.50    1.32    --  -43.81  38.00 120.00   96
 15  \w    -61.00 -33.00   0.50    1.32    --  -43.81 -38.00 120.00   56
 16  \w    -85.00 -29.00   0.50    1.32    --  -43.81 -38.00   0.00  112
 17  \w    -31.00  46.00   0.50    1.32    --   44.81 -57.00 -30.00  154
 18  \w     45.00  90.00   0.50    1.32    --   44.81-125.00-150.00   90
 19  \w    -44.00 -19.00   0.50    1.32    --  -88.13  61.00 120.00   50
 20  \w    -65.00 -28.00   0.50    1.32    --  -88.13  77.00  60.00   74
 21  \w   -164.00 -87.00   0.50    1.32    --  -88.13 -61.00-150.00  154
 22  \w    -44.00 -13.00   0.50    1.32    --  -88.13  61.00-150.00   62
 23  \w   -162.00 -89.00   0.50    1.32    --  -88.13 -61.00  90.00  146
 24  \w   -154.00-102.00   0.50    1.32    --  -88.13 -77.00 150.00  104
 25  \w     33.00  93.00   0.50    1.32    --  100.88 -95.00 -90.00  120
 26  \w     98.00 124.00   0.50    1.32    --  100.88  30.00 120.00   52
 27  \w     32.00  93.00   0.50    1.32    --  100.88 -95.00  30.00  122
 28  \w     30.00  55.00   0.50    1.32    --  100.88 -61.00  30.00   50
 29  \w     25.00  53.00   0.50    1.32    --  100.88 -61.00 -60.00   56
 30  \w     36.00  93.00   0.50    1.32    --  100.88 -95.00 120.00  114
 31  \w    124.00 149.00   0.50    1.32    --  100.88  77.00 -30.00   50
 32  \w    125.00 164.00   0.50    1.32    --  100.88  77.00   0.00   78
 33  \w    145.00 171.00   0.50    1.32    --  100.88  30.00 120.00   52
 34  \w     29.00  90.00   0.50    1.32    --  100.88 -95.00-150.00  122
 35  \w     68.00  93.00   0.50    1.32    --  109.87 -95.00  60.00   50
 36  \w     43.00  93.00   0.50    1.32    --  109.87 -95.00 -30.00  100
 37  \w     74.00 138.00   0.50    1.32    --  109.87  15.00-180.00  128
 38  \w     93.00 171.00   0.50    1.32    --  109.87  30.00  60.00  156
 39  \w     46.00  92.00   0.50    1.32    --  109.87 -95.00-120.00   92
 40  \w     38.00  93.00   0.50    1.32    --  109.87 -95.00-180.00  110
 41  \w     93.00 123.00   0.50    1.32    --  109.87  30.00  30.00   60
 42  \w     35.00  70.00   0.50    1.32    --  109.87-125.00 -30.00   70
 43  \w     41.00  66.00   0.50    1.32    --  109.87 -77.00  60.00   50
 44  \w     64.00  89.00   0.50    1.32    --  109.87 -95.00  90.00   50
 45  \w     43.00  91.00   0.50    1.32    --  109.87 -95.00 150.00   96
;
_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      -0.1034401000
_diffrn_orient_matrix_UB_12      0.0399166000
_diffrn_orient_matrix_UB_13      0.0561956000
_diffrn_orient_matrix_UB_21      0.1270208000
_diffrn_orient_matrix_UB_22      0.0393873000
_diffrn_orient_matrix_UB_23      0.0775782000
_diffrn_orient_matrix_UB_31      0.0480286000
_diffrn_orient_matrix_UB_32      0.1226167000
_diffrn_orient_matrix_UB_33      -0.0214777000
_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  0.0237
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19549
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.378
_diffrn_reflns_theta_min         2.816
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.907
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87248
_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    1.400
_exptl_crystal_description       block
_exptl_crystal_F_000             772
_exptl_crystal_preparation
;
Crystallised from a saturated solution of 4,4'-bipyridine
and methyl gallate (1:1) in MeOH.
;
_exptl_crystal_recrystallization_method
'High-throughput screening via the ENaCt protocol using SPT Labtech mosquito'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.047
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     516
_refine_ls_number_reflns         6898
_refine_ls_number_restraints     361
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0385
_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^)+(0.0645P)^2^+0.2163P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1126
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5569
_reflns_number_total             6898
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07556k2.cif
_cod_data_source_block           44-bipyridine_methylgallate_h2o
_cod_depositor_comments
;

2025-05-14
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel

 Adding full bibliography for 1574434--1574463.cif.
;
_cod_original_formula_moiety     '2(C8 H8 O5), 3(H2 O), 2(C10 H8 N2)'
_cod_original_formula_sum        'C36 H38 N4 O13'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     734.70
_cod_database_code               1574459
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.825
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H1Ba-H5A_$1
 2.2 with sigma of 0.04
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), C2C(H2C), C2F(H2F), C2G(H2G), C3C(H3C), C3G(H3G), C4C(H4C),
 C4G(H4G), C5C(H5C), C5G(H5G), C6A(H6A), C6F(H6F), C7C(H7C), C7G(H7G), C8C(H8C),
  C8G(H8G), C9C(H9C), C9G(H9G), C10C(H10C), C10G(H10G)
4.b Idealised Me refined as rotating group:
 C8A(H8Aa,H8Ab,H8Ac), C8F(H8Fa,H8Fb,H8Fc)
;
_shelx_res_checksum              17162
_shelx_hkl_checksum              18260
_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_methyl gallate_H2O'
_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 1.433
_oxdiff_exptl_absorpt_empirical_full_min 0.773