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_1548286
_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         'C22 H25 N O4'
_chemical_formula_sum            'C22 H25 N O4'
_chemical_formula_weight         367.43
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-08-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.731(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.2101(3)
_cell_length_b                   20.2873(7)
_cell_length_c                   21.2870(11)
_cell_measurement_reflns_used    6284
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      27.3170
_cell_measurement_theta_min      3.7290
_cell_volume                     3950.0(3)
_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)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3744
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -39.00  57.00   1.00   50.00    --  -11.22  57.00 150.00   96
  2  \w    -13.00  30.00   1.00   50.00    --  -11.22 -99.00-120.00   43
  3  \w     37.00  62.00   1.00   50.00    --  -11.22  37.00-150.00   25
  4  \w    -69.00  16.00   1.00   50.00    --  -11.22 -57.00-150.00   85
  5  \w    -38.00   0.00   1.00   50.00    --  -11.22  57.00 120.00   38
  6  \w    -83.00  -5.00   1.00   50.00    --  -11.22 -57.00   0.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Atlas'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0489020000
_diffrn_orient_matrix_UB_12      0.0046180000
_diffrn_orient_matrix_UB_13      -0.0279514000
_diffrn_orient_matrix_UB_21      -0.0527310000
_diffrn_orient_matrix_UB_22      0.0132675000
_diffrn_orient_matrix_UB_23      0.0182427000
_diffrn_orient_matrix_UB_31      0.0289006000
_diffrn_orient_matrix_UB_32      0.0320233000
_diffrn_orient_matrix_UB_33      -0.0035086000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            37480
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.229
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90184
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_description       plate
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.443
_exptl_crystal_size_mid          0.247
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         8073
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0477
_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^)+(0.0495P)^2^+0.5506P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1194
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5212
_reflns_number_total             8073
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00872_si_002.cif
_cod_data_source_block           YQ-11-P11-2_3_scale_compound_14
_cod_depositor_comments
'Adding full bibliography for 1548282--1548286.cif.'
_cod_database_code               1548286
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C6(H6), C36(H36)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C35(H35A,H35B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14), C17(H17), C18(H18), C20(H20),
 C21(H21), C40(H40), C41(H41), C43(H43), C44(H44), C47(H47), C48(H48), C50(H50),
  C51(H51)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C15(H15A,H15B,H15C), C22(H22A,H22B,H22C),
 C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C45(H45A,H45B,H45C), C52(H52A,H52B,
 H52C)
;
_shelx_res_checksum              75767
_shelx_hkl_checksum              61642
_ins_header
;
TITL YQ-11-P11-2_3_scale in P2(1)/c 
REM P2(1)/c (#14 in standard setting)
CELL 0.71073   9.210133  20.287314  21.286971  90.0000  96.7310  90.0000
ZERR    8.00   0.000349   0.000695   0.001058   0.0000   0.0038   0.0000
LATT  1
SYMM -x, y+1/2,-z+1/2 
SFAC C H N O
UNIT 176.00 200.00 8.00 32.00
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 1.109
_oxdiff_exptl_absorpt_empirical_full_min 0.892