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_7157621
_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         'C40 H35 N7 O12'
_chemical_formula_sum            'C40 H35 N7 O12'
_chemical_formula_weight         805.75
_space_group_crystal_system      trigonal
_space_group_IT_number           152
_space_group_name_Hall           'P 31 2"'
_space_group_name_H-M_alt        'P 31 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-03-24 deposited with the CCDC.	2020-07-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   19.7672(8)
_cell_length_b                   19.7672(8)
_cell_length_c                   23.6968(12)
_cell_measurement_reflns_used    5847
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.1160
_cell_measurement_theta_min      3.2860
_cell_volume                     8018.8(6)
_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    'ShelXT (Sheldrick, 2015)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -87.00  -59.70   0.7000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  178.0000  150.0000 39

  2 omega  -70.00   53.90   0.7000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106    0.0000  120.0000 177

  3 omega  -42.00   11.20   0.7000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106   19.0000   30.0000 76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0175588000
_diffrn_orient_matrix_UB_12      -0.0392682000
_diffrn_orient_matrix_UB_13      -0.0093801000
_diffrn_orient_matrix_UB_21      -0.0297968000
_diffrn_orient_matrix_UB_22      -0.0110978000
_diffrn_orient_matrix_UB_23      0.0205728000
_diffrn_orient_matrix_UB_31      -0.0228102000
_diffrn_orient_matrix_UB_32      0.0071383000
_diffrn_orient_matrix_UB_33      -0.0196121000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            34678
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.936
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71243
_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    1.001
_exptl_crystal_F_000             2520
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Flack x determined using 1764 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     536
_refine_ls_number_reflns         10925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1515
_refine_ls_R_factor_gt           0.0819
_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^)+(0.1419P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2096
_refine_ls_wR_factor_ref         0.2662
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                5441
_reflns_number_total             10925
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01172j2.cif
_cod_data_source_block           190510_s5_hh_0405b
_cod_depositor_comments
'Adding full bibliography for 7157620--7157628.cif.'
_cod_original_cell_volume        8018.8(8)
_cod_database_code               7157621
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.974
_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) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O2) = Uanis(O2A)
Uanis(C37) = Uanis(C36)
3. Others
 Sof(O2A)=1-FVAR(1)
 Sof(O2)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C17(H17), C25(H25)
4.b Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B)
4.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C20(H20), C21(H21),
 C22(H22), C23(H23), C24(H24), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32),
  C36(H36), C37(H37), C38(H38), C39(H39), C40(H40)
4.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              99331
_olex2_submission_special_instructions 'No special instructions were received'