Stereoselective synthesis of novel adamantane derivatives with high potency against rimantadine-resistant influenza A virus strains.
Kuznetsov, Nikolai Yu; Tikhov, Rabdan M.; Godovikov, Ivan A.; Medvedev, Michael G.; Lyssenko, Konstantin A.; Burtseva, Elena I.; Kirillova, Elena S.; Bubnov, Yuri N.; Organic & biomolecular chemistry 15 (2017) 3152–3157; doi:10.1039/c7ob00331e

data_7155530
_publ_section_title
;
 Stereoselective synthesis of novel adamantane derivatives with high
 potency against rimantadine-resistant influenza A virus strains.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3152
_journal_page_last               3157
_journal_paper_doi               10.1039/c7ob00331e
_journal_volume                  15
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H30 Br N O2'
_chemical_formula_sum            'C19 H30 Br N O2'
_chemical_formula_weight         384.35
_chemical_name_systematic
4-((3r,5r,7r)-adamantan-1-yl)-6-(bromomethyl)-2-(tert-butoxy)-5,6-dihydro-4H-1,3-oxazine
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-02-03
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2017-02-03 deposited with the CCDC.
2017-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6735(7)
_cell_length_b                   11.9007(8)
_cell_length_c                   14.2306(9)
_cell_measurement_reflns_used    8923
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.190
_cell_measurement_theta_min      2.231
_cell_volume                     1807.6(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            37724
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_min         2.231
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.284
_exptl_absorpt_correction_T_max  0.4926
_exptl_absorpt_correction_T_min  0.4206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1182 before and 0.0718 after correction. The Ratio of minimum to maximum transmission is 0.8538. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.362
_exptl_crystal_size_mid          0.252
_exptl_crystal_size_min          0.185
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.006(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         4820
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0298
_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^)+(0.0353P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0651
_refine_ls_wR_factor_ref         0.0680
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4269
_reflns_number_total             4820
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00331e2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7155527--7155531.cif.'
_cod_database_code               7155530
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.677
_shelx_estimated_absorpt_t_min   0.492
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.006(9) -0.006(9)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C4(H4), C6(H6), C10(H10), C12(H12), C15(H15)
3.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B), C9(H9A,H9B), C11(H11A,H11B), C13(H13A,H13B),
 C14(H14A,H14B), C16(H16A,H16B), C17(H17A,H17B)
3.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              44153
_olex2_submission_special_instructions 'No special instructions were received'