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_7157628
_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_formula_moiety         'C20 H27 N7 O12'
_chemical_formula_sum            'C20 H27 N7 O12'
_chemical_formula_weight         557.48
_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     iterative
_audit_creation_date             2020-01-02
_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                 101.469(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6273(12)
_cell_length_b                   8.8714(10)
_cell_length_c                   16.549(2)
_cell_measurement_reflns_used    1235
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.1530
_cell_measurement_theta_min      3.7500
_cell_volume                     1385.2(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(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measurement_details
;
  1 omega  -78.50    2.00   0.7000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -57.0000  -60.0000 115

  2 omega  -82.00   10.40   0.7000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -77.0000 -150.0000 132

  3 omega  -15.00   11.60   0.7000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       16.9200   95.0000 -179.0000 38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0681832000
_diffrn_orient_matrix_UB_12      -0.0145052000
_diffrn_orient_matrix_UB_13      0.0242412000
_diffrn_orient_matrix_UB_21      0.0316800000
_diffrn_orient_matrix_UB_22      0.0257861000
_diffrn_orient_matrix_UB_23      -0.0326221000
_diffrn_orient_matrix_UB_31      0.0023745000
_diffrn_orient_matrix_UB_32      0.0743059000
_diffrn_orient_matrix_UB_33      0.0160684000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6381
_diffrn_reflns_point_group_measured_fraction_full 0.755
_diffrn_reflns_point_group_measured_fraction_max 0.615
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.087
_diffrn_reflns_theta_min         2.969
_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  0.96830
_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    1.337
_exptl_crystal_F_000             584
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 616 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         4555
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      0.951
_refine_ls_R_factor_all          0.1129
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0421P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1215
_reflns_Friedel_coverage         0.350
_reflns_Friedel_fraction_full    0.476
_reflns_Friedel_fraction_max     0.340
_reflns_number_gt                2348
_reflns_number_total             4555
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01172j2.cif
_cod_data_source_block           190321_s2_hh
_cod_depositor_comments
'Adding full bibliography for 7157620--7157628.cif.'
_cod_database_code               7157628
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3
_reflns_odcompleteness_completeness 99.70
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C19-C20 = C19A-C20A
 1.55 with sigma of 0.02
 O11-C19 = O11A-C19A
 1.38 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C19) = Uanis(C19A)
Uanis(O12) = Uanis(O12A)
Uanis(C20) = Uanis(C20A)
Uanis(O11) = Uanis(O11A)
Uanis(O2) = Uanis(O2A)
Uanis(O5) = Uanis(O5A)
4. Others
 Sof(O12A)=Sof(C19A)=Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=1-FVAR(1)
 Sof(O12)=Sof(C19)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=FVAR(1)
 Sof(H18C)=Sof(H18D)=Sof(O11A)=1-FVAR(2)
 Sof(H18A)=Sof(H18B)=Sof(O11)=FVAR(2)
 Sof(O2A)=1-FVAR(3)
 Sof(O2)=FVAR(3)
 Sof(O5A)=1-FVAR(4)
 Sof(O5)=FVAR(4)
5.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C15(H15)
5.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C18(H18C,H18D)
5.c Aromatic/amide H refined with riding coordinates:
 N7(H7)
5.d 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), C20(H20A,H20B,H20C), C20A(H20D,H20E,H20F)
;
_shelx_res_checksum              54076
_olex2_submission_special_instructions 'No special instructions were received'