Molecular adduct of amantadine ferulate presents a pathway for slowing in vitro/vivo releases and raising synergistic antiviral effects via dual optimization salification strategy
Niu, Yuan-Yuan; Wang, Ling-Yang; Yu, Yue-Ming; Li, Yan-Tuan; Wu, Zhi-Yong; Yan, Cui-Wei; CrystEngComm 23 (2021) 4389–4401; doi:10.1039/D1CE00382H

data_7242971
_publ_section_title
;
 Molecular adduct of amantadine ferulate presents a pathway for slowing in
 vitro/vivo releases and raising synergistic antiviral effects via dual
 optimization salification strategy
;
_journal_issue                   24
_journal_name_full               CrystEngComm
_journal_page_first              4389
_journal_page_last               4401
_journal_paper_doi               10.1039/D1CE00382H
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         '(C10 H18 N +), (C10 H9 O4 -), 0.5(C3 H8 O)'
_chemical_formula_sum            'C21.5 H31 N O4.5'
_chemical_formula_weight         375.47
_chemical_melting_point          215.0
_chemical_name_common            'Amantadine ferulate isopropanol solvate'
_chemical_name_systematic
'1-Adamantylammonium 3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid propan-2-ol'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2021-01-06 deposited with the CCDC.	2021-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.122(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7505(4)
_cell_length_b                   10.1320(4)
_cell_length_c                   18.7022(8)
_cell_measurement_reflns_used    3833
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.2000
_cell_measurement_theta_min      4.3520
_cell_volume                     1983.93(14)
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  Bruker
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7925
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.175
_diffrn_reflns_theta_min         4.367
_exptl_absorpt_coefficient_mu    0.704
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       block
_exptl_crystal_F_000             812
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Isopropanol/ethanol'
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         3871
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0544P)^2^+0.5240P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1058
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3367
_reflns_number_total             3871
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00382h2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7242971.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C21.50 H31 N O4.50'
_cod_database_code               7242971
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_min   0.844
_shelx_estimated_absorpt_t_max   0.872
_shelx_res_checksum              19302
_shelx_hkl_checksum              96386