Understanding of Mirabegron Edisylate Hydrate Conversion and Solvate Characterisation
Balogh, Margareta Cristina; Claybourn, Boe M.; Bonnaud, Thierry; Pitak, Mateusz B.; CrystEngComm  (2026) –; doi:10.1039/D5CE00592B

data_7251881
_publ_section_title
;
 Understanding of Mirabegron Edisylate Hydrate Conversion and Solvate
 Characterisation
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D5CE00592B
_journal_year                    2026
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H26 N4 O2 S, C2 H4 O6 S2, 0.5(H2 O)'
_chemical_formula_sum            'C23 H31 N4 O8.5 S3'
_chemical_formula_weight         595.70
_chemical_name_common            'Mirabegron Edysilate hemihydrate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2024-10-02
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-10-02 deposited with the CCDC.	2026-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.7368(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.91352(16)
_cell_length_b                   10.64981(10)
_cell_length_c                   18.2350(2)
_cell_measurement_reflns_used    25941
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.7230
_cell_measurement_theta_min      2.6110
_cell_volume                     2671.13(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_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 0.999
_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     53.00  78.00   0.50    1.00    --   47.95  12.00-127.00   50
  2  \w     61.00  92.00   0.50    1.00    --   47.95  19.00 -60.00   62
  3  \w     85.00 111.00   0.50    1.00    --   47.95  77.00 -30.00   52
  4  \w    145.00 178.00   0.50    4.00    --  107.75  12.00-127.00   66
  5  \w    148.00 174.00   0.50    4.00    --  107.75  61.00 -30.00   52
  6  \w    144.00 176.00   0.50    4.00    --  107.75  77.00   0.00   64
  7  \w    153.00 178.00   0.50    4.00    --  107.75  77.00 -30.00   50
  8  \w    153.00 178.00   0.50    4.00    --  107.75 125.00  30.00   50
  9  \w    138.00 164.00   0.50    4.00    --  107.75  77.00-120.00   52
 10  \w    115.00 146.00   0.50    4.00    --  107.75 125.00-120.00   62
 11  \w     91.00 178.00   0.50    4.00    --  107.75  61.00 -90.00  174
 12  \w    151.00 176.00   0.50    4.00    --  107.75  15.00 -30.00   50
 13  \w     95.00 169.00   0.50    4.00    --  107.75  61.00  30.00  148
 14  \w     92.00 134.00   0.50    4.00    --  107.75  12.00-127.00   84
 15  \w     91.00 175.00   0.50    4.00    --  107.75  61.00 -60.00  168
 16  \w     93.00 162.00   0.50    4.00    --  107.75  61.00   0.00  138
 17  \w     96.00 128.00   0.50    4.00    --  107.75 125.00  30.00   64
 18  \w     86.00 112.00   0.50    4.00    --  107.75  77.00 -30.00   52
 19  \w     97.00 123.00   0.50    4.00    --  107.75  61.00 -30.00   52
 20  \w     85.00 124.00   0.50    4.00    --  107.75  77.00 -60.00   78
 21  \w     88.00 124.00   0.50    4.00    --  107.75  77.00 -90.00   72
 22  \w     85.00 111.00   0.50    4.00    --  107.75  77.00-120.00   52
 23  \w     85.00 138.00   0.50    4.00    --  107.75  77.00   0.00  106
 24  \w     85.00 134.00   0.50    4.00    --  107.75  77.00  30.00   98
 25  \w     28.00  60.00   0.50    1.00    --   47.95  77.00   0.00   64
 26  \w     33.00  59.00   0.50    1.00    --   47.95  57.00 -30.00   52
 27  \w     28.00  71.00   0.50    1.00    --   47.95  77.00  30.00   86
 28  \w     26.00  51.00   0.50    1.00    --   47.95  77.00 -30.00   50
 29  \w     25.00  65.00   0.50    1.00    --   47.95  77.00 -90.00   80
 30  \w    -24.00  26.00   0.50    1.00    --  -47.95  12.00-127.00  100
 31  \w    -26.00  27.00   0.50    1.00    --  -47.95  19.00   0.00  106
 32  \w    -55.00 -29.00   0.50    1.00    --  -47.95 -77.00-150.00   52
 33  \w    -89.00 -63.00   0.50    4.00    --  -86.25 -77.00 -60.00   52
 34  \w    -90.00 -64.00   0.50    4.00    --  -86.25 -77.00   0.00   52
 35  \w    -89.00 -63.00   0.50    4.00    --  -86.25 -79.00 -34.14   52
 36  \w    -88.00 -62.00   0.50    4.00    --  -86.25 -80.00 -72.91   52
 37  \w    -90.00 -64.00   0.50    4.00    --  -86.25 -76.00 -19.75   52
 38  \w    -88.00 -62.00   0.50    4.00    --  -86.25 -80.00  11.65   52
 39  \w    -88.00 -62.00   0.50    4.00    --  -86.25 -79.00 -49.05   52
 40  \w    -88.00 -63.00   0.50    4.00    --  -86.25 -77.00 -30.00   50
 41  \w    -94.00 -68.00   0.50    4.00    --  -86.25 -69.00 -79.28   52
 42  \w    -96.00 -67.00   0.50    4.00    --  -86.25 -69.00 -20.41   58
 43  \w    -89.00 -63.00   0.50    4.00    --  -86.25 -78.00 -38.87   52
 44  \w   -105.00 -36.00   0.50    1.00    --  -47.95 -37.00  30.00  138
 45  \w    -63.00 -33.00   0.50    1.00    --  -47.95 -57.00   0.00   60
 46  \w    -89.00 -63.00   0.50    4.00    --  -86.25 -80.00  48.05   52
 47  \w    -91.00 -65.00   0.50    4.00    --  -86.25 -77.00  30.00   52
 48  \w    -95.00 -62.00   0.50    4.00    --  -86.25 -79.00  54.99   66
 49  \w   -104.00 -65.00   0.50    4.00    --  -86.25 -72.00   6.73   78
 50  \w    -96.00 -69.00   0.50    4.00    --  -86.25 -69.00 -32.16   54
 51  \w    -96.00 -63.00   0.50    4.00    --  -86.25 -77.00 -90.00   66
 52  \w    -91.00 -62.00   0.50    4.00    --  -86.25 -80.00-106.86   58
 53  \w   -109.00 -35.00   0.50    1.00    --  -47.95 -45.00  -5.37  148
 54  \w    -50.00 -15.00   0.50    4.00    --  -86.25  45.00   0.00   70
 55  \w    -97.00 -65.00   0.50    4.00    --  -86.25 -75.00  23.54   64
 56  \w    -95.00 -69.00   0.50    4.00    --  -86.25 -72.00  14.98   52
 57  \w   -122.00 -33.00   0.50    1.00    --  -47.95 -12.00  60.00  178
 58  \w     37.00  70.00   0.50    4.00    --  107.75 -61.00 -90.00   66
 59  \w     72.00  98.00   0.50    4.00    --  107.75 -94.00 -30.00   52
 60  \w     60.00  86.00   0.50    4.00    --  107.75-125.00  60.00   52
 61  \w     87.00 112.00   0.50    4.00    --  107.75-125.00  60.00   50
 62  \w     44.00 100.00   0.50    4.00    --  107.75 -95.00 159.30  112
 63  \w     35.00  70.00   0.50    4.00    --  107.75 -61.00 150.00   70
 64  \w     37.00  70.00   0.50    4.00    --  107.75 -61.00   0.00   66
 65  \w     36.00  65.00   0.50    4.00    --  107.75 -94.00 -30.00   58
 66  \w     40.00  89.00   0.50    4.00    --  107.75 -77.00 -90.00   98
 67  \w     65.00 106.00   0.50    4.00    --  107.75 -94.00-180.00   82
 68  \w     36.00  64.00   0.50    4.00    --  107.75 -61.00-120.00   56
 69  \w     35.00  69.00   0.50    4.00    --  107.75 -61.00-180.00   68
 70  \w     36.00  70.00   0.50    4.00    --  107.75 -61.00-150.00   68
 71  \w     35.00  95.00   0.50    1.00    --   47.95-125.00-150.00  120
 72  \w    -26.00  20.00   0.50    1.00    --   47.95 -12.00  60.00   92
 73  \w   -140.00-115.00   0.50    4.00    --  -86.25 -12.00  60.00   50
 74  \w   -147.00-121.00   0.50    4.00    --  -86.25 -77.00 -30.00   52
 75  \w   -141.00-115.00   0.50    4.00    --  -86.25 -77.00 -90.00   52
;
_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      -0.0475170000
_diffrn_orient_matrix_UB_12      0.0193959000
_diffrn_orient_matrix_UB_13      -0.0906995000
_diffrn_orient_matrix_UB_21      -0.1014162000
_diffrn_orient_matrix_UB_22      -0.0123407000
_diffrn_orient_matrix_UB_23      0.0030692000
_diffrn_orient_matrix_UB_31      -0.0022992000
_diffrn_orient_matrix_UB_32      0.1427968000
_diffrn_orient_matrix_UB_33      0.0125497000
_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  0.0574
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            47589
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.244
_diffrn_reflns_theta_min         2.627
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.036
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.74a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_description       lath
_exptl_crystal_F_000             1252
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 4073 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.041(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     705
_refine_ls_number_reflns         9557
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0441
_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^)+(0.0555P)^2^+3.1224P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1121
_reflns_Friedel_coverage         0.848
_reflns_Friedel_fraction_full    0.954
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                9298
_reflns_number_total             9557
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00592b2.cif
_cod_data_source_block           p20098_3_r1
_cod_original_formula_sum        'C23 H31 N4 O8.50 S3'
_cod_database_code               7251881
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C23 H28 Cl2 N7 O4 S'
_chemical_oxdiff_usercomment
'MCB-1801-92-02 E,  P3716, Cu 100K, MP ,14SEP2020'
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.542
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB)
2.b Ternary CH refined with riding coordinates:
 C15A(H15A), C15B(H15B)
2.c Secondary CH2 refined with riding coordinates:
 N4A(H4AA,H4AB), C4A(H4AC,H4AD), C12A(H12A,H12B), C13A(H13A,H13B), C14A(H14A,
 H14B), N4B(H4BA,H4BB), C4B(H4BC,H4BD), C12B(H12C,H12D), C13B(H13C,H13D),
 C14B(H14C,H14D), C22A(H22A,H22B), C23A(H23A,H23B), C22B(H22C,H22D), C23B(H23C,
 H23D)
2.d Aromatic/amide H refined with riding coordinates:
 N2A(H2AA), N3A(H3A), C2A(H2AB), C7A(H7A), C8A(H8A), C10A(H10A), C11A(H11A),
 C17A(H17A), C18A(H18A), C19A(H19A), C20A(H20A), C21A(H21A), N2B(H2BA),
 N3B(H3B), C2B(H2BB), C7B(H7B), C8B(H8B), C10B(H10B), C11B(H11B), C17B(H17B),
 C18B(H18B), C19B(H19B), C20B(H20B), C21B(H21B)
2.e X=CH2 refined with riding coordinates:
 N1A(H1AA,H1AB), N1B(H1BA,H1BB)
;
_shelx_res_checksum              23408
_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 1.860
_oxdiff_exptl_absorpt_empirical_full_min 0.576