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_7250210
_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, C3 H6 O'
_chemical_formula_sum            'C29 H34 N6 O7 S'
_chemical_formula_weight         610.68
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-03-05
_audit_creation_method
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_audit_update_record
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2025-03-05 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                111.948(3)
_cell_angle_beta                 95.785(2)
_cell_angle_gamma                114.007(2)
_cell_formula_units_Z            2
_cell_length_a                   10.6139(6)
_cell_length_b                   13.0164(11)
_cell_length_c                   13.2023(8)
_cell_measurement_reflns_used    9994
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.59
_cell_volume                     1475.00(18)
_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
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0364
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            58823
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.369
_diffrn_reflns_theta_min         2.201
_diffrn_source                   'high brilliance microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            coloueless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       prism
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.610
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.166
_refine_diff_density_max         1.583
_refine_diff_density_min         -1.270
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       0.0054(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   1.166
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         7375
_refine_ls_number_restraints     1108
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0881
_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^)+(0.0403P)^2^+4.7706P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1976
_refine_ls_wR_factor_ref         0.2000
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6877
_reflns_number_total             7375
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce01228c2.cif
_cod_data_source_block           1a
_cod_depositor_comments
'Adding full bibliography for 7250208--7250210.cif.'
_cod_original_cell_volume        1474.99(18)
_cod_database_code               7250210
_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) groups, All
  N(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N4-C13
 1.45 with sigma of 0.02
 O2B-C15A = O2A-C15
 1.45 with sigma of 0.01
 N4-C14A = N4-C14 = C15-C14 = C15A-C14A
 1.45 with sigma of 0.005
 C16-C15 = C16A-C15A = O2A-C15 = O2B-C15A
 1.45 with sigma of 0.005
 N4-C14 \\sim N4-C14A
 with sigma of 0.02
 O2A-C15 \\sim O2B-C15A
 with sigma of 0.02
 C14-C15 \\sim C14A-C15A
 with sigma of 0.02
 C15-C16 \\sim C15A-C16A
 with sigma of 0.02
 C16-C17 \\sim C16A-C17A
 with sigma of 0.02
 C16-C21 \\sim C16A-C21A
 with sigma of 0.02
 C17-C18 \\sim C17A-C18A
 with sigma of 0.02
 C18-C19 \\sim C18A-C19A
 with sigma of 0.02
 C19-C20 \\sim C19A-C20A
 with sigma of 0.02
 C20-C21 \\sim C20A-C21A
 with sigma of 0.02
 N4-C15 \\sim N4-C15A
 with sigma of 0.04
 O2A-C14 \\sim O2B-C14A
 with sigma of 0.04
 O2A-C16 \\sim O2B-C16A
 with sigma of 0.04
 C14-C16 \\sim C14A-C16A
 with sigma of 0.04
 C15-C17 \\sim C15A-C17A
 with sigma of 0.04
 C15-C21 \\sim C15A-C21A
 with sigma of 0.04
 C16-C18 \\sim C16A-C18A
 with sigma of 0.04
 C16-C20 \\sim C16A-C20A
 with sigma of 0.04
 C17-C19 \\sim C17A-C19A
 with sigma of 0.04
 C17-C21 \\sim C17A-C21A
 with sigma of 0.04
 C18-C20 \\sim C18A-C20A
 with sigma of 0.04
 C19-C21 \\sim C19A-C21A
 with sigma of 0.04
3. Rigid bond restraints
 C24, C25
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
O2B \\sim O2A \\sim C15A \\sim C15 \\sim C14A \\sim C14 \\sim N4 \\sim C16A
\\sim C16 \\sim C17A \\sim C17 \\sim C18A \\sim C18 \\sim C19A \\sim C19 \\sim
C20 \\sim C21A \\sim C21 \\sim C20A: within 5A with sigma of 0.002 and sigma
for terminal atoms of 0.004 within 5A
5. Rigid body (RIGU) restrains
 O2A, C15, C14, N4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 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
 O2B, C15A, C14A, N4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C15A, C16A, C17A, C18A, C19A, C20A, C21A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
6. Others
 Sof(H4BC)=Sof(H4BD)=Sof(O2B)=Sof(H2B)=Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(C15A)=
 Sof(H15A)=Sof(C16A)=Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=
 Sof(H19A)=Sof(C20A)=Sof(H20A)=Sof(C21A)=Sof(H21A)=1-FVAR(1)
 Sof(H4AA)=Sof(H4AB)=Sof(O2A)=Sof(H2A)=Sof(C14)=Sof(H14A)=Sof(H14B)=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)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C15(H15), C15A(H15A)
7.b Secondary CH2 refined with riding coordinates:
 N4(H4AA,H4AB), N4(H4BC,H4BD), C4(H4A,H4B), C12(H12A,H12B), C13(H13A,H13B),
 C14(H14A,H14B), C14A(H14C,H14D)
7.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C7(H7), C8(H8), C10(H10), C11(H11), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), N5(H5), N6(H6), C24(H24), C17A(H17A), C18A(H18A),
  C19A(H19A), C20A(H20A), C21A(H21A)
7.d Fitted hexagon refined as free rotating group:
 C16(C17,C18,C19,C20,C21), C16A(C17A,C18A,C19A,C20A,C21A)
7.e X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
7.f Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C30(H30A,H30B,H30C)
7.g Idealised tetrahedral OH refined as rotating group:
 O2A(H2A), O2B(H2B)
;
_shelx_res_checksum              21602
_olex2_submission_special_instructions 'No special instructions were received'