Synthesis and antiviral activity of novel spirocyclic nucleosides
Cobb, Alexander J. A.; Dell’Isola, Antonio; Abdulsattar, Ban O.; McLachlan, Matthew M. W.; Neuman, Benjamin W.; Müller, Christin; Shankland, Kenneth; Al-Mulla, Hawaa M. N.; Binks, Alexander W. D.; Elvidge, Warren; New Journal of Chemistry 42 (2018) 18363–; doi:10.1039/C8NJ02777C

data_7057826
_publ_section_title
;
 Synthesis and antiviral activity of novel spirocyclic nucleosides
;
_journal_issue                   22
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              18363
_journal_paper_doi               10.1039/C8NJ02777C
_journal_volume                  42
_journal_year                    2018
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C12 H17 N3 O5'
_chemical_formula_sum            'C12 H17 N3 O5'
_chemical_formula_weight         283.28
_chemical_name_systematic
(3'aR,6'R,6'aR,7R)-2',2'-dimethyl-octahydro-3'aH-spiro[[1,2,3]triazolo[4,3-c][1,4]oxazine-7,4'-furo[3,4-d][1,3]dioxol]-6'-ylmethanol
_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   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2018-03-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-04-28 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.596(5)
_cell_length_b                   8.066(5)
_cell_length_c                   24.761(5)
_cell_measurement_reflns_used    4772
_cell_measurement_temperature    150.00(14)
_cell_measurement_theta_max      29.2134
_cell_measurement_theta_min      3.0079
_cell_volume                     1317.4(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_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    'SIR97 (Burla et al., 2007)'
_diffrn_ambient_temperature      150.00(14)
_diffrn_detector_area_resol_mean 16.2086
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_details
;
  1 omega  -62.00   45.00   1.0000   17.2300
omega____ theta____ kappa____ phi______ frames
    -      -17.7198   19.0000    0.0000 107

  2 omega  -37.00    2.00   1.0000   17.2300
omega____ theta____ kappa____ phi______ frames
    -      -17.7198   77.0000 -150.0000 39

  3 omega  -86.00  -60.00   1.0000   17.2300
omega____ theta____ kappa____ phi______ frames
    -      -17.7198 -178.0000   30.0000 26

  4 omega  -90.00    8.00   1.0000   17.2300
omega____ theta____ kappa____ phi______ frames
    -      -17.7198  -38.0000 -180.0000 98

  5 omega  -94.00  -46.00   1.0000   17.2300
omega____ theta____ kappa____ phi______ frames
    -      -17.7198 -178.0000   90.0000 48

  6 omega  -87.00    4.00   1.0000   17.2300
omega____ theta____ kappa____ phi______ frames
    -      -17.7198  -57.0000  -30.0000 91

  7 omega   -4.00   61.00   1.0000   17.2300
omega____ theta____ kappa____ phi______ frames
    -       18.6573  -99.0000   90.0000 65

  8 omega  -22.00   27.00   1.0000   17.2300
omega____ theta____ kappa____ phi______ frames
    -       18.6573   97.0000  158.0000 49
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1041648000
_diffrn_orient_matrix_UB_12      0.0085633000
_diffrn_orient_matrix_UB_13      0.0065570000
_diffrn_orient_matrix_UB_21      -0.0267111000
_diffrn_orient_matrix_UB_22      0.0294099000
_diffrn_orient_matrix_UB_23      0.0260245000
_diffrn_orient_matrix_UB_31      0.0013976000
_diffrn_orient_matrix_UB_32      -0.0825056000
_diffrn_orient_matrix_UB_33      0.0099328000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            13779
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.280
_diffrn_reflns_theta_min         3.014
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99413
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1004 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3179
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0427
_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^)+(0.0315P)^2^+0.2114P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0779
_refine_ls_wR_factor_ref         0.0816
_reflns_Friedel_coverage         0.659
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.844
_reflns_number_gt                2860
_reflns_number_total             3179
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj02777c2.cif
_cod_data_source_block           17A
_cod_depositor_comments
'Adding full bibliography for 7057826--7057827.cif.'
_cod_database_code               7057826
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         C12H17N3O5
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
;
_shelx_res_checksum              54457
_olex2_submission_special_instructions 'No special instructions were received'