A light- and heat-driven glycal diazidation approach to nitrogenous carbohydrate derivatives with antiviral activity.
He, Huan; Cao, Ruiyuan; Cao, Ruidi; Liu, Xiao-Yu; Li, Wei; Yu, Di; Li, Yuexiang; Liu, Miaomiao; Wu, Yanmei; Wu, Pingzhou; Yang, Jin-Song; Yan, Yunzheng; Yang, Jingjing; Zheng, Zhi-Bing; Zhong, Wu; Qin, Yong; Organic & biomolecular chemistry 18 (2020) 6155–6161; doi:10.1039/d0ob01172j

data_7157624
_publ_section_title
;
 A light- and heat-driven glycal diazidation approach to nitrogenous
 carbohydrate derivatives with antiviral activity.
;
_journal_issue                   31
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6155
_journal_page_last               6161
_journal_paper_doi               10.1039/d0ob01172j
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C13 H16 N6 O8'
_chemical_formula_sum            'C13 H16 N6 O8'
_chemical_formula_weight         384.32
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-02-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-02 deposited with the CCDC.	2020-07-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2784(7)
_cell_length_b                   9.2019(10)
_cell_length_c                   26.166(3)
_cell_measurement_reflns_used    1361
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.1730
_cell_measurement_theta_min      3.6430
_cell_volume                     1752.5(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   21.00   48.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       17.0762  -99.0000    0.0000 54

  2 omega   -3.00   23.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -99.0000 -180.0000 52

  3 omega  -82.00  -34.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -77.0000    0.0000 96

  4 omega  -78.00  -17.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -57.0000  -90.0000 122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0073803000
_diffrn_orient_matrix_UB_12      0.0767235000
_diffrn_orient_matrix_UB_13      -0.0016163000
_diffrn_orient_matrix_UB_21      0.0083203000
_diffrn_orient_matrix_UB_22      0.0050967000
_diffrn_orient_matrix_UB_23      0.0269799000
_diffrn_orient_matrix_UB_31      0.0966986000
_diffrn_orient_matrix_UB_32      0.0055113000
_diffrn_orient_matrix_UB_33      -0.0024360000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6084
_diffrn_reflns_point_group_measured_fraction_full 0.919
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         3.114
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 635 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3278
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0461
_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^)+(0.0383P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0950
_reflns_Friedel_coverage         0.575
_reflns_Friedel_fraction_full    0.808
_reflns_Friedel_fraction_max     0.797
_reflns_number_gt                2428
_reflns_number_total             3278
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01172j2.cif
_cod_data_source_block           190226_s4_yd_2
_cod_depositor_comments
'Adding full bibliography for 7157620--7157628.cif.'
_cod_original_cell_volume        1752.4(3)
_cod_database_code               7157624
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.958
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O8) = Uanis(O8A)
3. Others
 Sof(H10C)=Sof(H10D)=Sof(O8A)=1-FVAR(1)
 Sof(H10A)=Sof(H10B)=Sof(O8)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C6(H6), C9(H9)
4.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C10(H10C,H10D)
4.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              41082
_olex2_submission_special_instructions 'No special instructions were received'