A unique spiro-β-triazinedione-γ-hydantoin type alkaloid with antiviral activity against tobacco mosaic virus from Streptomyces gamaensis
Guo, Xiaowei; Wang, Jidong; Su, Can; Liu, Chongxi; Ma, Xiao-Yan; Yu, Zhiyin; Li, Jiansong; Wang, Xiangjing; Xiang, Wensheng; Huang, Sheng-Xiong; Organic Chemistry Frontiers 6 (2019) 3215–; doi:10.1039/C9QO00742C

data_1555038
_publ_section_title
;
 A unique spiro-\b-triazinedione-\g-hydantoin type alkaloid with antiviral
 activity against tobacco mosaic virus from Streptomyces gamaensis
;
_journal_issue                   18
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3215
_journal_paper_doi               10.1039/C9QO00742C
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C9 H13 N5 O4'
_chemical_formula_sum            'C9 H13 N5 O4'
_chemical_formula_weight         255.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-08
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2019-03-24 deposited with the CCDC.	2019-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.2310(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3117(2)
_cell_length_b                   17.2043(4)
_cell_length_c                   8.3018(2)
_cell_measurement_reflns_used    6074
_cell_measurement_temperature    130
_cell_measurement_theta_max      69.315
_cell_measurement_theta_min      5.141
_cell_volume                     1155.62(5)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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      130
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8428
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.354
_diffrn_reflns_theta_min         5.142
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.003
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.5033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0961 before and 0.0445 after correction.
The Ratio of minimum to maximum transmission is 0.6682.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.808
_refine_diff_density_min         -0.748
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.0088(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.674
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2084
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.674
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0477
_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^)+(0.0930P)^2^+3.1499P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1260
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2029
_reflns_number_total             2084
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00742c2.cif
_cod_data_source_block           dm16178
_cod_database_code               1555038
_shelx_estimated_absorpt_t_max   0.825
_shelx_estimated_absorpt_t_min   0.788
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              65474
_shelx_hkl_checksum              93935
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'