New salt-solvates of Mirabegron: a combined experimental and computational study
Prohens, Rafel; Barbas, Rafael; Barceló-Oliver, Miquel; Frontera, Antonio; CrystEngComm 27 (2025) 2720–2728; doi:10.1039/D4CE01228C

data_7250208
_publ_section_title
;
 New salt-solvates of Mirabegron: a combined experimental and
 computational study
;
_journal_issue                   17
_journal_name_full               CrystEngComm
_journal_page_first              2720
_journal_page_last               2728
_journal_paper_doi               10.1039/D4CE01228C
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C21 H25 N4 O2 S, C5 H3 N2 O4, 0.5[C3H8O]'
_chemical_formula_sum            'C27.5 H32 N6 O6.5 S'
_chemical_formula_weight         582.65
_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_creation_date             2025-01-30
_audit_creation_method
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-03-05 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                100.627(5)
_cell_angle_beta                 97.557(5)
_cell_angle_gamma                98.458(5)
_cell_formula_units_Z            2
_cell_length_a                   7.0067(9)
_cell_length_b                   11.6243(15)
_cell_length_c                   17.481(2)
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.37
_cell_volume                     1365.6(3)
_computing_cell_refinement       'Bruker Apex5, 2024'
_computing_data_collection       'Bruker Apex5, 2024'
_computing_data_reduction        'SAINT v8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            56404
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.373
_diffrn_reflns_theta_min         2.372
_diffrn_source                   'high brilliance microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       block
_exptl_crystal_F_000             614
_exptl_crystal_size_max          0.811
_exptl_crystal_size_mid          0.303
_exptl_crystal_size_min          0.175
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       0.0112(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.296
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     449
_refine_ls_number_reflns         6797
_refine_ls_number_restraints     138
_refine_ls_restrained_S_all      1.290
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0889
_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^)+6.1431P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1985
_refine_ls_wR_factor_ref         0.2001
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6376
_reflns_number_total             6797
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce01228c2.cif
_cod_data_source_block           1b
_cod_depositor_comments
'Adding full bibliography for 7250208--7250210.cif.'
_cod_original_formula_sum        'C27.50 H32 N6 O6.50 S'
_cod_database_code               7250208
_shelx_shelxl_version_number     2019/3
_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,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O2-C15
 1.4 with sigma of 0.01
 C21-C20 = C20A-C21A = C21A-C16A = C21-C16 = C17A-C16A = C17-C16 = C19A-C20A =
 C20-C19 = C18-C17 = C17A-C18A = C19-C18 = C18A-C19A
 1.36 with sigma of 0.02
 C15A-C14A = C15-C14A
 1.5 with sigma of 0.02
 C16-C15 = C16A-C15A
 1.5 with sigma of 0.02
 C14-C15
 1.5 with sigma of 0.02
 N4-C14 = N4-C14A
 1.5 with sigma of 0.02
 N1-H1B = N1-H1A
 0.93 with sigma of 0.02
 N3-H3
 0.93 with sigma of 0.02
 N4-C15 \\sim N4-C15A
 with sigma of 0.04
3. Restrained planarity
 H1B, H1A, N1, C1
 with sigma of 0.1
4. Rigid body (RIGU) restrains
 N4, C14A, C15A, C16A, C21A, C20A, C19A, C18A, C17A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 N4, C14, C15, C16, C17, C18, C19, C20, C21
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
5. Others
 Sof(H4BC)=Sof(H4BD)=Sof(C14A)=Sof(H14A)=Sof(H14B)=Sof(C15A)=Sof(H15A)=
 Sof(O2A)=Sof(H2A)=Sof(C21A)=Sof(H21A)=Sof(C18A)=Sof(H18A)=Sof(C17A)=Sof(H17A)=
 Sof(C20A)=Sof(H20A)=Sof(C16A)=Sof(C19A)=Sof(H19A)=1-FVAR(1)
 Sof(H4AA)=Sof(H4AB)=Sof(O2)=Sof(H2)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(C17)=
 Sof(H17)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20)=Sof(C21)=
 Sof(H21)=Sof(C14)=Sof(H14C)=Sof(H14D)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C15(H15), C15A(H15A)
6.b Secondary CH2 refined with riding coordinates:
 N4(H4BC,H4BD), N4(H4AA,H4AB), C4(H4A,H4B), C12(H12A,H12B), C13(H13A,H13B),
 C14A(H14A,H14B), C14(H14C,H14D)
6.c Aromatic/amide H refined with riding coordinates:
 N5(H5), N6(H6), C3(H3A), C7(H7), C8(H8), C10(H10), C11(H11), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21), C26(H26), C21A(H21A), C18A(H18A),
 C17A(H17A), C20A(H20A), C19A(H19A)
6.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O2A(H2A)
;
_smtbx_masks_special_details
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A solvent mask was calculated and 35 electrons were 
found in a volume of 139\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
0.5[C3H8O] per formula unit 
which account for 34 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              28575
_shelx_fab_checksum              5509
_olex2_submission_special_instructions 'No special instructions were received'