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_4035030
_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_formula_moiety         'C14 H17 N O6 S'
_chemical_formula_sum            'C14 H17 N O6 S'
_chemical_formula_weight         327.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-04-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.058(17)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.642(3)
_cell_length_b                   8.5259(7)
_cell_length_c                   21.871(3)
_cell_measurement_reflns_used    4277
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.1950
_cell_measurement_theta_min      2.9240
_cell_volume                     2966.7(8)
_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, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.3271
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
  1 omega   55.00  101.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       43.0073   37.0000   60.0000 23

  2 omega   22.00  100.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       43.0073   57.0000    0.0000 39

  3 omega   -8.00   64.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       43.0073  -37.0000   30.0000 36

  4 omega   35.00   85.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5026  -45.0000    0.0000 25

  5 omega   76.00  108.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5026  -94.0000  -60.0000 16

  6 omega   60.00   96.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5026 -125.0000 -180.0000 18

  7 omega   36.00   74.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5026  -94.0000  -60.0000 19

  8 omega   32.00   92.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5026  -94.0000   30.0000 30

  9 omega   31.00   89.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5026  -30.0000   90.0000 29

 10 omega   38.00   68.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5026  -45.0000  150.0000 15

 11 omega   29.00  145.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5026  -15.0000  150.0000 58
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'GV1000, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0915749000
_diffrn_orient_matrix_UB_12      -0.0288850000
_diffrn_orient_matrix_UB_13      0.0003885000
_diffrn_orient_matrix_UB_21      0.0272601000
_diffrn_orient_matrix_UB_22      -0.0073693000
_diffrn_orient_matrix_UB_23      0.0735319000
_diffrn_orient_matrix_UB_31      -0.0160641000
_diffrn_orient_matrix_UB_32      -0.1782969000
_diffrn_orient_matrix_UB_33      -0.0031137000
_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_radiation_wavelength_determination fundamental
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11518
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.342
_diffrn_reflns_theta_min         2.956
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    2.221
_exptl_absorpt_correction_T_max  0.666
_exptl_absorpt_correction_T_min  0.411
_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    1.466
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of toluene and hexane  by slow evaporation'
_exptl_crystal_size_max          0.6941
_exptl_crystal_size_mid          0.3884
_exptl_crystal_size_min          0.2363
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.00081(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         5849
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0657P)^2^+1.0343P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1139
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5204
_reflns_number_total             5849
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01258_si_005.cif
_cod_data_source_block           adpcmf
_cod_database_code               4035030
_nottingham_internal_coll_name   ADPCMF
_nottingham_internal_coll_number 13590
_nottingham_internal_coll_client ADP/CJM
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time 2.0000
_nottingham_internal_coll_frame_width 2.0000
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   12/05/2014
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_date 12/05/2014
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 12/5/2014
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 12/5/2014
_nottingham_internal_refinement_user pczwl
_nottingham_internal_validation_date 13/5/2014
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 13/5/2014
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C14 H17 N O6 S'
_reflns_odcompleteness_completeness 99.58
_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 C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C42, C39, C41, C40, C41A, C40A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(H39C)=Sof(H39D)=Sof(H42C)=Sof(H42D)=Sof(C40A)=Sof(H40C)=Sof(H40D)=
 Sof(C41A)=Sof(H41C)=Sof(H41D)=1-FVAR(1)
 Sof(H39A)=Sof(H39B)=Sof(H42A)=Sof(H42B)=Sof(C40)=Sof(H40A)=Sof(H40B)=Sof(C41)=
 Sof(H41A)=Sof(H41B)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B),
 C39(H39A,H39B), C39(H39C,H39D), C42(H42A,H42B), C42(H42C,H42D), C43(H43A,H43B),
  C40(H40A,H40B), C40A(H40C,H40D), C41(H41A,H41B), C41A(H41C,H41D)
4.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C38(H38)
4.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C22(H22A,H22B,H22C), C48(H48A,H48B,H48C), C52(H52A,H52B,
 H52C)
;
_shelx_res_checksum              50501
_shelx_hkl_checksum              74413
_olex2_date_sample_data_collection 2014-05-12
_olex2_date_sample_submission    2014-05-09
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perflourotether oil'
_olex2_submission_special_instructions 'No special instructions were received'