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_7157620
_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 ad
_chemical_formula_moiety         'C20 H27 N7 O12'
_chemical_formula_sum            'C20 H27 N7 O12'
_chemical_formula_weight         557.48
_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     direct
_audit_creation_date             2019-01-15
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_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                   9.29096(14)
_cell_length_b                   14.5006(2)
_cell_length_c                   20.3184(3)
_cell_measurement_reflns_used    5984
_cell_measurement_temperature    291.6(2)
_cell_measurement_theta_max      72.3320
_cell_measurement_theta_min      3.7320
_cell_volume                     2737.39(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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_environment      air
_diffrn_ambient_temperature      291.6(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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   -104.00 -10.00   1.00    1.08    --  -36.42 -77.00 120.00   94
  2  \w   -107.00 -44.00   1.00    1.08    --  -36.42-167.00 142.00   63
  3  \w     10.00 104.00   1.00    1.08    --   36.42  77.00 -30.00   94
  4  \w     23.00  90.00   1.00    1.08    --   36.42-125.00 120.00   67
  5  \w     20.00 104.00   1.00    1.08    --   36.42  57.00-120.00   84
  6  \w     39.00 130.00   1.00    4.31    --  108.71 -30.00   0.00   91
  7  \w     39.00 109.00   1.00    4.31    --  108.71 -94.00 -90.00   70
  8  \w     41.00 135.00   1.00    4.31    --  108.71 -77.00   0.00   94
  9  \w     39.00 109.00   1.00    4.31    --  108.71 -94.00 150.00   70
 10  \w     39.00 130.00   1.00    4.31    --  108.71 -30.00 -60.00   91
 11  \w    100.00 178.00   1.00    4.31    --  108.71 111.00-180.00   78
 12  \w     39.00 130.00   1.00    4.31    --  108.71 -30.00  90.00   91
 13  \w   -106.00 -18.00   1.00    1.08    --  -36.42 -38.00   0.00   88
 14  \w    -55.00  15.00   1.00    1.08    --  -36.42  38.00 150.00   70
 15  \w    -31.00  53.00   1.00    1.08    --   36.42 -57.00 -30.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0182013000
_diffrn_orient_matrix_UB_12      -0.0493148000
_diffrn_orient_matrix_UB_13      -0.0666486000
_diffrn_orient_matrix_UB_21      0.0217078000
_diffrn_orient_matrix_UB_22      -0.0938605000
_diffrn_orient_matrix_UB_23      0.0341396000
_diffrn_orient_matrix_UB_31      -0.1633419000
_diffrn_orient_matrix_UB_32      -0.0069744000
_diffrn_orient_matrix_UB_33      0.0119150000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15433
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.958
_diffrn_reflns_theta_min         3.745
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.975
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 1906 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         5368
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0540
_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^)+(0.1068P)^2^+0.0504P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1492
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                4912
_reflns_number_total             5368
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01172j2.cif
_cod_data_source_block           qy-hh181126e
_cod_depositor_comments
'Adding full bibliography for 7157620--7157628.cif.'
_cod_original_cell_volume        2737.38(7)
_cod_database_code               7157620
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00F(H00F), C00G(H00G), C00I(H00I), C00J(H00J), C00Q(H00Q), C00S(H00S)
2.b Secondary CH2 refined with riding coordinates:
 C00U(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 N008(H008)
2.d Idealised Me refined as rotating group:
 C00X(H00C,H00D,H00E), C00Y(H00H,H00K,H00L), C00Z(H00M,H00N,H00O), C010(H01A,
 H01B,H01C), C012(H01D,H01E,H01F), C013(H01G,H01H,H01I)
;
_shelx_res_checksum              98932
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2019-01-14
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.537
_oxdiff_exptl_absorpt_empirical_full_min 0.785