Synthesis of the 1,2,4-Thiadiazole Alkaloid Polyaurine B
Anstis, Daniel G.; Lindsay, Ashley C.; Söhnel, Tilo; Sperry, Jonathan; Journal of Natural Products  (2020) –; doi:10.1021/acs.jnatprod.0c00166

data_1557810
_publ_section_title
;
 Synthesis of the 1,2,4-Thiadiazole Alkaloid Polyaurine B
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.0c00166
_journal_year                    2020
_chemical_formula_moiety         'C12 H15 N3 O4'
_chemical_formula_sum            'C12 H15 N3 O4'
_chemical_formula_weight         265.27
_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
_audit_creation_date             2020-02-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.673(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.63730(10)
_cell_length_b                   13.1251(2)
_cell_length_c                   14.4267(2)
_cell_measurement_reflns_used    8386
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.8210
_cell_measurement_theta_min      6.2020
_cell_volume                     1238.92(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_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    -64.00  14.00   0.50    0.50    --  -47.48  38.00 120.00  156
  2  \w    -50.00 -25.00   0.50    2.00    --  -90.25 118.00 149.00   50
  3  \w    -70.00 -45.00   0.50    0.50    --  -47.48 118.00 149.00   50
  4  \w    -95.00 -70.00   0.50    0.50    --  -47.48 160.00 -58.00   50
  5  \w     78.00 103.00   0.50    0.50    --   47.48 160.00 -58.00   50
  6  \w    103.00 129.00   0.50    2.00    --  101.53 160.00 -58.00   52
  7  \w    115.00 149.00   0.50    2.00    --  101.53 178.00   0.00   68
  8  \w    120.00 174.00   0.50    2.00    --  101.53 118.00 149.00  108
  9  \w     82.00 154.00   0.50    2.00    --  101.53  30.00  90.00  144
 10  \w     69.00 105.00   0.50    2.00    --  101.53 -45.00  30.00   72
 11  \w     60.00  89.00   0.50    0.50    --   47.48-118.00  62.00   58
 12  \w     87.00 114.00   0.50    2.00    --  101.53-118.00  62.00   54
 13  \w     82.00 111.00   0.50    2.00    --  101.53-111.00 150.00   58
 14  \w     36.00  63.00   0.50    2.00    --  101.53 -45.00  30.00   54
 15  \w     25.00 109.00   0.50    2.00    --  101.53 -95.00  60.00  168
 16  \w     61.00  86.00   0.50    0.50    --   47.48-160.00 -89.00   50
 17  \w     97.00 129.00   0.50    2.00    --  101.53-160.00 -89.00   64
 18  \w     29.00 106.00   0.50    2.00    --  101.53 -61.00 -90.00  154
 19  \w     73.00 157.00   0.50    2.00    --  101.53  15.00-150.00  168
 20  \w    130.00 173.00   0.50    2.00    --  101.53  61.00-120.00   86
 21  \w    108.00 161.00   0.50    2.00    --  101.53 111.00-150.00  106
 22  \w     84.00 110.00   0.50    0.50    --   47.48  77.00-150.00   52
 23  \w     80.00 121.00   0.50    2.00    --  101.53  61.00-120.00   82
 24  \w     59.00 133.00   0.50    2.00    --  101.53 178.00-120.00  148
 25  \w     61.00  87.00   0.50    2.00    --  101.53 178.00   0.00   52
 26  \w     23.00  60.00   0.50    0.50    --   47.48  77.00-150.00   74
 27  \w    -73.00 -37.00   0.50    0.50    --  -47.48 -57.00  90.00   72
 28  \w   -120.00 -78.00   0.50    0.50    --  -47.48-118.00  62.00   84
 29  \w   -123.00 -86.00   0.50    0.50    --  -47.48-125.00  90.00   74
 30  \w   -146.00 -97.00   0.50    2.00    --  -90.25-118.00  62.00   98
 31  \w   -159.00-133.00   0.50    2.00    --  -90.25 -77.00 -60.00   52
 32  \w   -130.00-105.00   0.50    2.00    --  -90.25 -77.00 -60.00   50
 33  \w   -120.00 -40.00   0.50    0.50    --  -47.48 -57.00 -90.00  160
 34  \w   -110.00 -85.00   0.50    0.50    --  -47.48-160.00 -89.00   50
 35  \w    -90.00 -46.00   0.50    2.00    --  -90.25-160.00 -89.00   88
 36  \w   -123.00 -73.00   0.50    0.50    --  -47.48-125.00-180.00  100
 37  \w   -144.00 -82.00   0.50    2.00    --  -90.25 -95.00-180.00  124
 38  \w   -164.00 -75.00   0.50    2.00    --  -90.25 -45.00-120.00  178
 39  \w   -168.00-125.00   0.50    2.00    --  -90.25-111.00  90.00   86
 40  \w    -87.00 -62.00   0.50    2.00    --  -90.25 111.00 -60.00   50
 41  \w    -48.00 -22.00   0.50    2.00    --  -90.25 111.00 -60.00   52
 42  \w    -95.00 -70.00   0.50    2.00    --  -90.25 160.00 -58.00   50
 43  \w     28.00  53.00   0.50    2.00    --  101.53-111.00 150.00   50
 44  \w     36.00 109.00   0.50    2.00    --  101.53-111.00 -60.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1392978000
_diffrn_orient_matrix_UB_12      0.0322841000
_diffrn_orient_matrix_UB_13      -0.0701631000
_diffrn_orient_matrix_UB_21      0.0124818000
_diffrn_orient_matrix_UB_22      -0.1116901000
_diffrn_orient_matrix_UB_23      -0.0314331000
_diffrn_orient_matrix_UB_31      -0.1893965000
_diffrn_orient_matrix_UB_32      0.0163718000
_diffrn_orient_matrix_UB_33      -0.0762747000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15882
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.392
_diffrn_reflns_theta_min         4.584
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.912
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2487
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0323
_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^)+(0.0445P)^2^+0.3827P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0889
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2190
_reflns_number_total             2487
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00166_si_002.cif
_cod_data_source_block           dap6_3
_cod_database_code               1557810
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C12H15N3O4
_shelx_estimated_absorpt_t_max   0.914
_shelx_estimated_absorpt_t_min   0.883
_diffrn_oxdiff_digest_frames
;
01b650aea8e520ae187e48b7c4df075a2c000478f59
;
_diffrn_oxdiff_digest_hkl
;
010e4b780b7035a148ecd538caa25d5d8d2e9c
;
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C)
;
_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 1.402
_oxdiff_exptl_absorpt_empirical_full_min 0.839