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_7157627
_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         'C17 H22 N6 O11'
_chemical_formula_sum            'C17 H22 N6 O11'
_chemical_formula_weight         486.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-04-22
_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                 91.458(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.7778(5)
_cell_length_b                   13.2995(10)
_cell_length_c                   11.4128(6)
_cell_measurement_reflns_used    1527
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.3780
_cell_measurement_theta_min      3.4800
_cell_volume                     1180.17(13)
_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    'ShelXS (Sheldrick, 2008)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   15.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       17.0762   38.0000   30.0000 71

  2 omega   -8.00   20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -99.0000  -30.0000 28

  3 omega  -16.00   22.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -99.0000 -120.0000 38

  4 omega  -68.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106 -178.0000  -30.0000 32

  5 omega  -80.00  -41.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  178.0000   30.0000 39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0853317000
_diffrn_orient_matrix_UB_12      0.0118794000
_diffrn_orient_matrix_UB_13      0.0185984000
_diffrn_orient_matrix_UB_21      0.0321979000
_diffrn_orient_matrix_UB_22      -0.0353351000
_diffrn_orient_matrix_UB_23      -0.0404735000
_diffrn_orient_matrix_UB_31      0.0031759000
_diffrn_orient_matrix_UB_32      0.0380842000
_diffrn_orient_matrix_UB_33      -0.0434049000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5262
_diffrn_reflns_point_group_measured_fraction_full 0.682
_diffrn_reflns_point_group_measured_fraction_max 0.669
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         3.035
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99740
_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    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 516 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         3233
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0410
_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^)+(0.0476P)^2^+0.0116P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0994
_reflns_Friedel_coverage         0.282
_reflns_Friedel_fraction_full    0.334
_reflns_Friedel_fraction_max     0.308
_reflns_number_gt                2434
_reflns_number_total             3233
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01172j2.cif
_cod_data_source_block           190419_s2_hh_yd0417b
_cod_depositor_comments
'Adding full bibliography for 7157620--7157628.cif.'
_cod_original_cell_volume        1180.18(13)
_cod_database_code               7157627
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.961
_reflns_odcompleteness_completeness 99.84
_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) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C),
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              99116
_olex2_submission_special_instructions 'No special instructions were received'