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_7250209
_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, C4 H7 O2, C2 H3 N'
_chemical_formula_sum            'C27 H35 N5 O4 S'
_chemical_formula_weight         525.66
_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             2025-03-05
_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                81.610(4)
_cell_angle_beta                 88.461(4)
_cell_angle_gamma                83.493(3)
_cell_formula_units_Z            2
_cell_length_a                   7.9585(6)
_cell_length_b                   9.7595(8)
_cell_length_c                   18.6559(16)
_cell_measurement_reflns_used    9968
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.25
_cell_volume                     1424.2(2)
_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 1.000
_diffrn_measured_fraction_theta_max 0.995
_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  0.0616
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7062
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.321
_diffrn_reflns_theta_min         2.122
_diffrn_source                   'high brilliance microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.313
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.101
_refine_diff_density_max         0.822
_refine_diff_density_min         -0.959
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.0081(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   1.177
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     432
_refine_ls_number_reflns         7062
_refine_ls_number_restraints     606
_refine_ls_restrained_S_all      1.205
_refine_ls_R_factor_all          0.1098
_refine_ls_R_factor_gt           0.0955
_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^)+5.6596P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1957
_refine_ls_wR_factor_ref         0.2012
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5911
_reflns_number_total             7062
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce01228c2.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7250208--7250210.cif.'
_cod_database_code               7250209
_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
  O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1-H1
 0.9 with sigma of 0.01
 H1-O4_$2
 1.9 with sigma of 0.01
 O1-C15
 1.45 with sigma of 0.01
 O3-H1A_$1 = C9-C10 = C11-C10 = C6-C11 = C9-C8
 1.39 with sigma of 0.02
 C6-C11A = C11A-C10A = C9-C10A = C9-C8A = C8A-C7A = C7A-C6
 1.39 with sigma of 0.02
 C6-C11 \\sim C6-C11A
 with sigma of 0.02
 C8-C9 \\sim C8A-C9
 with sigma of 0.02
 C9-C10 \\sim C9-C10A
 with sigma of 0.02
 C10-C11 \\sim C10A-C11A
 with sigma of 0.02
 C6-C8 \\sim C6-C8A
 with sigma of 0.04
 C6-C10 \\sim C6-C10A
 with sigma of 0.04
 C9-C11 \\sim C9-C11A
 with sigma of 0.04
 C23-C24 \\sim C23-C24A
 with sigma of 0.02
 C23-C25 \\sim C23-C25A
 with sigma of 0.02
 C3N-H3NA \\sim C6N-H6NA
 with sigma of 0.02
 C3N-H3NB \\sim C6N-H6NB
 with sigma of 0.02
 C3N-H3NC \\sim C6N-H6NC
 with sigma of 0.02
 C3N-C2N \\sim C6N-C5N
 with sigma of 0.02
 C2N-N1N \\sim C5N-N4N
 with sigma of 0.02
 C3N-N1N \\sim C6N-N4N
 with sigma of 0.04
 H3NA-H3NB \\sim H6NA-H6NB
 with sigma of 0.04
 H3NA-H3NC \\sim H6NA-H6NC
 with sigma of 0.04
 H3NA-C2N \\sim H6NA-C5N
 with sigma of 0.04
 H3NB-H3NC \\sim H6NB-H6NC
 with sigma of 0.04
 H3NB-C2N \\sim H6NB-C5N
 with sigma of 0.04
 H3NC-C2N \\sim H6NC-C5N
 with sigma of 0.04
3. Restrained planarity
 C11, C10, C12, C9, C8, C6, N2
 with sigma of 0.1
 C6, C8, C9, C10, C11, N2, C12
 with sigma of 0.1
 C6, C9, C7A, C10A, C8A, C11A, N2, C12
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C24A \\sim C24 \\sim C23 \\sim C25 \\sim C25A \\sim C22: within 5A with sigma
of 0.002 and sigma for terminal atoms of 0.004 within 5A
N1N \\sim C2N \\sim N4N \\sim C5N \\sim C3N \\sim C6N: within 5A with sigma of
0.002 and sigma for terminal atoms of 0.004 within 5A
C8 \\sim C8A \\sim C9 \\sim C10 \\sim C10A \\sim C11 \\sim C11A \\sim C6 \\sim
C7A \\sim C7: within 5A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 5A
5. Rigid body (RIGU) restrains
 C9, C8, C7, C6, C11, C10
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C11A, C10A, C9, C8A, C7A, C6
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C24, C23, C25
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C24A, C23, C25A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 N4N, C5N, C6N
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 N1N, C2N, C3N
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
6. Others
 Sof(C11A)=Sof(H11A)=Sof(C10A)=Sof(H10A)=Sof(C8A)=Sof(H8A)=Sof(C7A)=Sof(H7A)=1-
 FVAR(1)
 Sof(C8)=Sof(H8)=Sof(C10)=Sof(H10)=Sof(C11)=Sof(H11)=Sof(C7)=Sof(H7)=FVAR(1)
 Sof(H23A)=Sof(C25A)=Sof(H25D)=Sof(H25E)=Sof(H25F)=Sof(C24A)=Sof(H24D)=
 Sof(H24E)=Sof(H24F)=1-FVAR(2)
 Sof(H23)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=Sof(C25)=Sof(H25A)=Sof(H25B)=
 Sof(H25C)=FVAR(2)
 Sof(O1')=Sof(H1')=1-FVAR(3)
 Sof(O1)=Sof(H1)=FVAR(3)
 Sof(N4N)=Sof(C5N)=Sof(C6N)=Sof(H6NA)=Sof(H6NB)=Sof(H6NC)=1-FVAR(4)
 Sof(C3N)=Sof(H3NA)=Sof(H3NB)=Sof(H3NC)=Sof(C2N)=Sof(N1N)=FVAR(4)
 Fixed Sof: H15(0.5) H15A(0.5)
7.a Ternary CH refined with riding coordinates:
 C15(H15), C15(H15A), C23(H23), C23(H23A)
7.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C4(H4C,H4D), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
7.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C11A(H11A), C10A(H10A), C8A(H8A), C7A(H7A), C8(H8), C10(H10),
  C11(H11), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C7(H7)
7.d Fitted hexagon refined as free rotating group:
 C6(C11A,C10A,C9,C8A,C7A)
7.e X=CH2 refined with riding coordinates:
 N4(H4A,H4B)
7.f Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C25A(H25D,H25E,H25F), C24A(H24D,
 H24E,H24F), C3N(H3NA,H3NB,H3NC), C6N(H6NA,H6NB,H6NC)
;
_shelx_res_checksum              55454
_olex2_submission_special_instructions 'No special instructions were received'