Nitrosporeusines A and B, Unprecedented Thioester-Bearing Alkaloids from the ArcticStreptomyces nitrosporeus
Yang, Aigang; Si, Longlong; Shi, Zhenping; Tian, Li; Liu, Dong; Zhou, Demin; Proksch, Peter; Lin, Wenhan; Organic Letters 15 (2013) 5366–; doi:10.1021/ol4026809

data_1512591
_publ_section_title
;
 Nitrosporeusines A and B, Unprecedented Thioester-Bearing Alkaloids from
 the ArcticStreptomyces nitrosporeus
;
_journal_issue                   20
_journal_name_full               'Organic Letters'
_journal_page_first              5366
_journal_paper_doi               10.1021/ol4026809
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H13 N O5 S'
_chemical_formula_sum            'C14 H13 N O5 S'
_chemical_formula_weight         307.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-06-20
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1030(3)
_cell_length_b                   23.0098(8)
_cell_length_c                   7.3274(2)
_cell_measurement_reflns_used    2607
_cell_measurement_temperature    98.0
_cell_measurement_theta_max      71.6686
_cell_measurement_theta_min      3.8390
_cell_volume                     1366.18(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_diffrn_ambient_temperature      98.0
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
  1 omega  -16.00   11.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   99.0000  -20.0000 27

  2 omega  -30.00   30.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000   30.0000 60

  3 omega  -47.00   18.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000 -180.0000 65

  4 omega   -9.00   20.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   45.0000  -30.0000 29

  5 omega  -49.00   23.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000 -120.0000 72

  6 omega   32.00   97.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   37.0000 -180.0000 65

  7 omega   60.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000 -150.0000 118

  8 omega   41.00   96.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   30.0000 55

  9 omega   48.00   95.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  120.0000 47

 10 omega  100.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  -90.0000 78

 11 omega  115.00  151.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000    0.0000 36

 12 omega   43.00  133.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -70.0000  -67.0000 90
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1153624000
_diffrn_orient_matrix_UB_12      -0.0516029000
_diffrn_orient_matrix_UB_13      -0.0530470000
_diffrn_orient_matrix_UB_21      -0.0876587000
_diffrn_orient_matrix_UB_22      0.1727051000
_diffrn_orient_matrix_UB_23      -0.0015069000
_diffrn_orient_matrix_UB_31      0.1520977000
_diffrn_orient_matrix_UB_32      0.0603820000
_diffrn_orient_matrix_UB_33      -0.0409324000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4389
_diffrn_reflns_theta_full        71.81
_diffrn_reflns_theta_max         71.81
_diffrn_reflns_theta_min         3.84
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.322
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.50
_refine_diff_density_max         1.127
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2602
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.192
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0589
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0778P)^2^+3.0879P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1675
_refine_ls_wR_factor_ref         0.1676
_reflns_number_gt                2590
_reflns_number_total             2602
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4026809_si_003.cif
_cod_data_source_block           exp_1428
_cod_database_code               1512591
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97