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_7157625
_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     dual
_audit_creation_date             2019-04-19
_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                 90.320(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.2129(4)
_cell_length_b                   40.7685(17)
_cell_length_c                   12.8563(5)
_cell_measurement_reflns_used    6267
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.7900
_cell_measurement_theta_min      3.3450
_cell_volume                     4828.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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 0.959
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -25.00  23.00   0.20    1.00    --  -15.63 -99.00 -90.00  240
  2  \w    -25.00   0.00   0.20    1.00    --  -15.63 -99.00-150.00  125
  3  \w    -74.00 -35.00   0.20    1.00    --  -15.63-178.00-120.00  195
  4  \w    -19.00  21.00   0.20    1.00    --   17.66-105.00  78.00  200
  5  \w     33.00  88.00   0.20    1.00    --   17.66-178.00 150.00  275
  6  \w    -43.00 -18.00   0.20    1.00    --  -15.63 105.00 179.00  125
  7  \w     40.00  69.00   0.20    1.00    --   17.66 178.00-180.00  145
  8  \w    -51.00  38.00   0.20    1.00    --   17.35 -19.00-180.00  445
  9  \w      9.00  42.00   0.20    1.00    --   17.35  38.00  60.00  165
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0589358000
_diffrn_orient_matrix_UB_12      -0.0104924000
_diffrn_orient_matrix_UB_13      0.0121406000
_diffrn_orient_matrix_UB_21      -0.0491009000
_diffrn_orient_matrix_UB_22      0.0131436000
_diffrn_orient_matrix_UB_23      -0.0079464000
_diffrn_orient_matrix_UB_31      -0.0065448000
_diffrn_orient_matrix_UB_32      -0.0043841000
_diffrn_orient_matrix_UB_33      -0.0532753000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            35580
_diffrn_reflns_point_group_measured_fraction_full 0.853
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.905
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       block
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 3926 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1253
_refine_ls_number_reflns         16488
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0499
_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^)+(0.0642P)^2^+0.1049P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1318
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    0.745
_reflns_Friedel_fraction_max     0.718
_reflns_number_gt                11897
_reflns_number_total             16488
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01172j2.cif
_cod_data_source_block           190419_s1_hh_yd0417a
_cod_depositor_comments
'Adding full bibliography for 7157620--7157628.cif.'
_cod_database_code               7157625
_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 94.72
_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(O33) = Uanis(O33A)
Uanis(O44) = Uanis(O44A)
3. Others
 Sof(O33A)=1-FVAR(1)
 Sof(O33)=FVAR(1)
 Sof(O44A)=1-FVAR(2)
 Sof(O44)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C19(H19), C20(H20), C21(H21),
 C22(H22), C29(H29), C36(H36), C37(H37), C38(H38), C39(H39), C46(H46), C53(H53),
  C54(H54), C55(H55), C56(H56), C63(H63)
4.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C32(H32A,H32B), C49(H49A,H49B), C66(H66A,H66B)
4.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), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C28(H28A,H28B,
 H28C), C31(H31A,H31B,H31C), C34(H34A,H34B,H34C), C41(H41A,H41B,H41C), C43(H43A,
 H43B,H43C), C45(H45A,H45B,H45C), C48(H48A,H48B,H48C), C51(H51A,H51B,H51C),
 C58(H58A,H58B,H58C), C60(H60A,H60B,H60C), C62(H62A,H62B,H62C), C65(H65A,H65B,
 H65C), C68(H68A,H68B,H68C)
;
_shelx_res_checksum              32157
_olex2_date_sample_data_collection 2009-06-13
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.058
_oxdiff_exptl_absorpt_empirical_full_min 0.920