Total Synthesis of the Marine Alkaloid Discoipyrrole C via the MoOPH-Mediated Oxidation of a 2,3,5-Trisubstituted Pyrrole.
Yan, Qiao; Ma, Xiang; Banwell, Martin G.; Ward, Jas S.; Journal of natural products 80 (2017) 3305–3313; doi:10.1021/acs.jnatprod.7b00872

data_1548282
_publ_section_title
;
 Total Synthesis of the Marine Alkaloid Discoipyrrole C via the
 MoOPH-Mediated Oxidation of a 2,3,5-Trisubstituted Pyrrole.
;
_journal_issue                   12
_journal_name_full               'Journal of natural products'
_journal_page_first              3305
_journal_page_last               3313
_journal_paper_doi               10.1021/acs.jnatprod.7b00872
_journal_volume                  80
_journal_year                    2017
_chemical_formula_moiety         'C20 H21 N O4'
_chemical_formula_sum            'C20 H21 N O4'
_chemical_formula_weight         339.38
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2017-09-01
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.3150(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.87260(10)
_cell_length_b                   12.68010(10)
_cell_length_c                   18.1414(2)
_cell_measurement_reflns_used    9340
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.5940
_cell_measurement_theta_min      4.8560
_cell_volume                     2269.19(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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    -26.00  94.00   1.00    1.00    --   36.95   0.00 -60.00  120
  2  \w     45.00 122.00   1.00    3.50    --  111.00 -38.00  90.00   77
  3  \w     82.00 116.00   1.00    3.50    --  111.00-111.00 -30.00   34
  4  \w     93.00 143.00   1.00    3.50    --  111.00 -92.00 -30.00   50
  5  \w     69.00 119.00   1.00    3.50    --  111.00 -64.00 -60.00   50
  6  \w     60.00 116.00   1.00    3.50    --  111.00-111.00-180.00   56
  7  \w     45.00 128.00   1.00    3.50    --  111.00 -50.00-180.00   83
  8  \w     92.00 178.00   1.00    3.50    --  111.00  38.00 -90.00   86
  9  \w    143.00 174.00   1.00    3.50    --  111.00  50.00 -60.00   31
 10  \w     97.00 128.00   1.00    3.50    --  111.00  50.00 -60.00   31
 11  \w     67.00 178.00   1.00    3.50    --  111.00  12.00  30.00  111
 12  \w     54.00 129.00   1.00    3.50    --  111.00 -25.00 -30.00   75
 13  \w     58.00 111.00   1.00    3.50    --  111.00 -50.00   0.00   53
 14  \w     44.00  87.00   1.00    3.50    --  111.00 -92.00 -30.00   43
 15  \w     42.00 115.00   1.00    3.50    --  111.00 -38.00 -90.00   73
 16  \w     43.00 126.00   1.00    3.50    --  111.00 -77.00-180.00   83
 17  \w     30.00  80.00   1.00    1.00    --   36.95-125.00-150.00   50
 18  \w     -9.00  68.00   1.00    1.00    --   36.95 -88.00  -7.00   77
 19  \w     14.00  76.00   1.00    1.00    --   36.95 -99.00  60.00   62
 20  \w     43.00 115.00   1.00    3.50    --  111.00-111.00 150.00   72
 21  \w     20.00 102.00   1.00    1.00    --   36.95  57.00 150.00   82
 22  \w     10.00 105.00   1.00    1.00    --   36.95  77.00 -90.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0283519000
_diffrn_orient_matrix_UB_12      -0.0970572000
_diffrn_orient_matrix_UB_13      0.0480422000
_diffrn_orient_matrix_UB_21      -0.0574832000
_diffrn_orient_matrix_UB_22      0.0723635000
_diffrn_orient_matrix_UB_23      0.0593576000
_diffrn_orient_matrix_UB_31      -0.1424181000
_diffrn_orient_matrix_UB_32      -0.0098540000
_diffrn_orient_matrix_UB_33      -0.0373534000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16213
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.752
_diffrn_reflns_theta_min         4.255
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.564
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    0.993
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.104
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4554
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0421P)^2^+0.6795P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0917
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4193
_reflns_number_total             4554
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00872_si_002.cif
_cod_data_source_block           YQ-5-3_2_scale_sq_compound_3
_cod_depositor_comments
'Adding full bibliography for 1548282--1548286.cif.'
_cod_database_code               1548282
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, H2 of O2, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, H4 of O4, H3 of O3
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14), C16(H16), C17(H17), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              83374
_shelx_hkl_checksum              53306
_shelx_fab_checksum              25795
_ins_header
;
TITL YQ-5-3_2_scale in P2(1)/n 
REM P2(1)/n (#14 in standard setting)
CELL 1.54184   9.872637  12.680097  18.141359  90.0000  92.3150  90.0000
ZERR    4.00   0.000073   0.000107   0.000153   0.0000   0.0007   0.0000
LATT  1
SYMM -x+1/2, y+1/2,-z+1/2 
SFAC C H N O
UNIT 96.00 116.00 4.00 24.00
TREF
HKLF 4
END
;
_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 1.235
_oxdiff_exptl_absorpt_empirical_full_min 0.813