Origin of the Thiopyrone CTP-431 "Unexpectedly" Isolated from the Marine Sponge Cacospongia mycofijiensis.
Przeslak, Adam D.; Inman, Martyn; Lewis, William; Moody, Christopher J.; The Journal of organic chemistry 83 (2018) 10595–10601; doi:10.1021/acs.joc.8b01258

data_4035031
_publ_section_title
;
 Origin of the Thiopyrone CTP-431 &quot;Unexpectedly&quot; Isolated from
 the Marine Sponge Cacospongia mycofijiensis.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10595
_journal_page_last               10601
_journal_paper_doi               10.1021/acs.joc.8b01258
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H17 N O3 S'
_chemical_formula_sum            'C11 H17 N O3 S'
_chemical_formula_weight         243.31
_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   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-10-03
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.342(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.7848(8)
_cell_length_b                   5.5237(6)
_cell_length_c                   12.4287(12)
_cell_measurement_reflns_used    1881
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.1160
_cell_measurement_theta_min      5.1480
_cell_volume                     595.10(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.3613
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
  1 omega  -48.00    6.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   29.0000   49.0000 54

  2 omega  -41.00   32.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000  150.0000 73

  3 omega  -48.00   23.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000   90.0000 71

  4 omega   19.00  108.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1277   57.0000  120.0000 89

  5 omega   55.00   82.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1277   38.0000 -150.0000 27

  6 omega   15.00   78.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1277   77.0000 -180.0000 63

  7 omega   85.00  168.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   45.0000 -150.0000 83

  8 omega  100.00  177.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822  125.0000 -150.0000 77

  9 omega  100.00  127.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822  125.0000  -90.0000 27

 10 omega  126.00  177.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   77.0000  150.0000 51

 11 omega   84.00  111.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   45.0000   90.0000 27

 12 omega   76.00  102.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   77.0000   60.0000 26

 13 omega  113.00  172.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   77.0000   60.0000 59

 14 omega   76.00  103.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   77.0000  120.0000 27

 15 omega   83.00  111.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   61.0000 -180.0000 28

 16 omega   79.00  106.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   77.0000  150.0000 27

 17 omega   82.00  111.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   61.0000   90.0000 29

 18 omega   33.00   91.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822  -30.0000  120.0000 58

 19 omega  121.00  177.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   77.0000   90.0000 56

 20 omega   86.00  115.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   61.0000  120.0000 29

 21 omega   80.00  110.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   61.0000  150.0000 30

 22 omega  123.00  175.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   77.0000  120.0000 52

 23 omega   82.00  109.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   77.0000   90.0000 27

 24 omega   77.00  104.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   77.0000 -180.0000 27

 25 omega   36.00   84.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822  -30.0000   60.0000 48

 26 omega   84.00  126.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   45.0000 -180.0000 42

 27 omega   83.00  110.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   45.0000  120.0000 27

 28 omega   85.00  112.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   45.0000  150.0000 27

 29 omega  148.00  175.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822  125.0000  -90.0000 27
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_UB_11      0.1661680000
_diffrn_orient_matrix_UB_12      0.0883434000
_diffrn_orient_matrix_UB_13      0.0391396000
_diffrn_orient_matrix_UB_21      -0.0187875000
_diffrn_orient_matrix_UB_22      -0.0528507000
_diffrn_orient_matrix_UB_23      0.1188740000
_diffrn_orient_matrix_UB_31      0.0603316000
_diffrn_orient_matrix_UB_32      -0.2591200000
_diffrn_orient_matrix_UB_33      -0.0107589000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_unetI/netI     0.0710
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4795
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.991
_diffrn_reflns_theta_min         3.604
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    2.371
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.679
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       needle
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.4098
_exptl_crystal_size_mid          0.0529
_exptl_crystal_size_min          0.0167
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.109
_refine_ls_abs_structure_details
;
 Flack x determined using 730 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2293
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0678
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1079P)^2^+0.2451P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1678
_refine_ls_wR_factor_ref         0.1790
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    0.926
_reflns_Friedel_fraction_max     0.883
_reflns_number_gt                2045
_reflns_number_total             2293
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01258_si_004.cif
_cod_data_source_block           adpcmg
_cod_database_code               4035031
_nottingham_internal_coll_name   ADPCMG
_nottingham_internal_coll_number 13939
_nottingham_internal_coll_client ADP/CJM
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time '20.0000, 80.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   28/08/2014
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_date 02/10/2014
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 28/8/2014
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 2/10/2014
_nottingham_internal_refinement_user pczwl
_nottingham_internal_validation_date 3/10/2014
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 3/10/2014
_chemical_oxdiff_formula         'C11 H19 N O4 S'
_chemical_oxdiff_usercomment
'ADPCMG #13939 SN-275 IN FOMBLIN FILM ON A MICROMOUNT FOR ADP/CJM'
_reflns_odcompleteness_completeness 100.00
_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:
 C3(H3), C5(H5), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C9(H9A,H9B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              73115
_shelx_hkl_checksum              18334
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'