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_7156348
_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         'C31 H25 N3 O4 S'
_chemical_formula_sum            'C31 H25 N3 O4 S'
_chemical_formula_weight         535.62
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             16-07-25
_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                 90.966(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.5193(13)
_cell_length_b                   11.6263(7)
_cell_length_c                   9.3856(5)
_cell_measurement_reflns_used    1769
_cell_measurement_temperature    150
_cell_measurement_theta_max      71
_cell_measurement_theta_min      4
_cell_volume                     2566.1(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2016)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2016)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2016)'
_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_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.079
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16907
_diffrn_reflns_theta_full        67.958
_diffrn_reflns_theta_max         72.273
_diffrn_reflns_theta_min         3.759
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.482
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro version 1.171.38.43 (Rigaku Oxford Diffraction, 2016)
(Release 29 April 2016; compiled 27 May 2016,16:53)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.014
_refine_diff_density_max         0.61
_refine_diff_density_min         -0.68
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         4953
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1170
_refine_ls_R_factor_gt           0.0706
_refine_ls_shift/su_max          0.0001434
_refine_ls_shift/su_mean         0.0000139
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 2.75P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1532
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1532
_reflns_limit_h_max              28
_reflns_limit_h_min              -28
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                3162
_reflns_number_total             4953
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.67
_oxford_diffrn_Wilson_scale      0.07
_oxford_refine_ls_r_factor_ref   0.1170
_oxford_refine_ls_scale          4.01(7)
_oxford_reflns_number_all        4953
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'Z:\kel1608SN\Tony_kel1608SN_data At 16:34 on'
_cod_data_source_file            c8ob00865e2.cif
_cod_data_source_block           kel1608SN
_cod_depositor_comments
'Adding full bibliography for 7156347--7156351.cif.'
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               7156348
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE N   (   2,X'S) H   (   2,X'S) 
RIDE N   (   3,X'S) H   (   3,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) H   ( 312,X'S) H   ( 313,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;