Cascade reactions of indigo with oxiranes and aziridines: efficient access to dihydropyrazinodiindoles and spiro-oxazocinodiindoles.
Butler, Nicholas M.; Hendra, Rudi; Bremner, John B.; Willis, Anthony C.; Lucantoni, Leonardo; Avery, Vicky M.; Keller, Paul A.; Organic & biomolecular chemistry 16 (2018) 6006–6016; doi:10.1039/c8ob00865e

data_7156347
_publ_section_title
;
 Cascade reactions of indigo with oxiranes and aziridines: efficient
 access to dihydropyrazinodiindoles and spiro-oxazocinodiindoles.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6006
_journal_page_last               6016
_journal_paper_doi               10.1039/c8ob00865e
_journal_volume                  16
_journal_year                    2018
_chemical_compound_source        ' from U of Wollongong'
_chemical_formula_moiety         'C19 H14 N2 O3'
_chemical_formula_sum            'C19 H14 N2 O3'
_chemical_formula_weight         318.33
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             15-09-09
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2017-12-10 deposited with the CCDC.
2018-07-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.8798(1)
_cell_length_b                   18.4104(1)
_cell_length_c                   14.5081(1)
_cell_measurement_reflns_used    33874
_cell_measurement_temperature    150
_cell_measurement_theta_max      72
_cell_measurement_theta_min      5
_cell_volume                     2905.99(4)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Supernova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            54126
_diffrn_reflns_theta_full        72.334
_diffrn_reflns_theta_max         72.334
_diffrn_reflns_theta_min         4.721
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.819
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.359
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0045
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         2881
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/su_max          0.0005888
_refine_ls_shift/su_mean         0.0001237
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 1.27P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0746
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0746
_reflns_limit_h_max              13
_reflns_limit_h_min              0
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                2749
_reflns_number_total             2881
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.08
_oxford_diffrn_Wilson_scale      0.05
_oxford_refine_ls_r_factor_ref   0.0316
_oxford_refine_ls_scale          4.19(5)
_oxford_reflns_number_all        2881
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'Z:\kel1511SN\Tony_kel1511SN_data At 14:56 on'
_cod_data_source_file            c8ob00865e2.cif
_cod_data_source_block           kel1511SN
_cod_depositor_comments
'Adding full bibliography for 7156347--7156351.cif.'
_cod_original_sg_symbol_Hall     '-P 2ab 2ac '
_cod_original_sg_symbol_H-M      'P c c n '
_cod_database_code               7156347
_iucr_refine_instruction_details_constraints
;
BLOCK 
CONT SCALE 
CONT O    (    1 ,X'S,U'S)  UNTIL C    (   19 ) 
CONT H    (    2 ,X'S)  UNTIL H    (  192 ) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;