Total synthesis of (-)-agelastatin A: an S<sub>H</sub>2' radical azidation strategy.
Tsuchimochi, Izuru; Kitamura, Yuta; Aoyama, Hiroshi; Akai, Shuji; Nakai, Keiyo; Yoshimitsu, Takehiko; Chemical communications (Cambridge, England) 54 (2018) 9893–9896; doi:10.1039/c8cc05697h

data_7122116
_publ_section_title
;
 Total synthesis of (-)-agelastatin A: an S<sub>H</sub>2' radical
 azidation strategy.
;
_journal_issue                   71
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9893
_journal_page_last               9896
_journal_paper_doi               10.1039/c8cc05697h
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C16 H23 Br1 N2 O2 Si1'
_chemical_formula_sum            'C32 H46 Br2 N4 O4 Si2'
_chemical_formula_weight         766.73
_chemical_name_systematic
(1R,3aS,9aS)-1-Azido-2-((tert-butyldimethylsilyl)oxy)-1,3a,4,9a-tetrahydro-5H-cyclopenta[e]pyrrolo[1,2-a]pyrazin-5-one
_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'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-06-25T17:10:37-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2018-06-30 deposited with the CCDC.
2018-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.239(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.0818(2)
_cell_length_b                   34.0727(11)
_cell_length_c                   8.0223(15)
_cell_measurement_reflns_used    7629
_cell_measurement_temperature    163(2)
_cell_measurement_theta_max      68.14
_cell_measurement_theta_min      5.195
_cell_measurement_wavelength     1.54178
_cell_volume                     1867.7(4)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction
'CrystalClear (Rigaku/MSC Inc., 2006), SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      163(2)
_diffrn_detector                 'curved image-plate'
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'quarter \C-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku R-Axis Rapid'
_diffrn_measurement_method       'phi or omega oscillation scans'
_diffrn_orient_matrix_type       fs_process
_diffrn_orient_matrix_UB_11      -0.067198
_diffrn_orient_matrix_UB_12      0.023114
_diffrn_orient_matrix_UB_13      0.035639
_diffrn_orient_matrix_UB_21      -0.059019
_diffrn_orient_matrix_UB_22      0.006676
_diffrn_orient_matrix_UB_23      -0.124176
_diffrn_orient_matrix_UB_31      -0.115847
_diffrn_orient_matrix_UB_32      -0.016809
_diffrn_orient_matrix_UB_33      -0.00031
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0866
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            18514
_diffrn_reflns_point_group_measured_fraction_full 0.98
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.202
_diffrn_reflns_theta_min         5.192
_diffrn_source                   'sealed x-ray tube'
_exptl_absorpt_coefficient_mu    3.679
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.008
_refine_diff_density_min         -1.24
_refine_diff_density_rms         0.141
_refine_ls_abs_structure_details
;
 Flack x determined using 1033 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.046(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         6688
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.1839
_refine_ls_R_factor_gt           0.0987
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1376P)^2^+5.0614P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2276
_refine_ls_wR_factor_ref         0.3234
_reflns_number_gt                3190
_reflns_number_total             6688
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc05697h2.cif
_cod_data_source_block           160625
_cod_depositor_comments          'Adding full bibliography for 7122116.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7122116