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_7156349
_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         'C23 H18 N2 O6'
_chemical_formula_sum            'C23 H18 N2 O6'
_chemical_formula_weight         418.41
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             16-03-02
_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                 90.165(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.9584(7)
_cell_length_b                   9.6484(3)
_cell_length_c                   16.0090(6)
_cell_measurement_reflns_used    15550
_cell_measurement_temperature    150
_cell_measurement_theta_max      29
_cell_measurement_theta_min      2
_cell_volume                     3700.6(2)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2015)'
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb 9 2015,16:26:32)
;
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2015)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.931
_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         'Supermova (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            39146
_diffrn_reflns_theta_full        27.572
_diffrn_reflns_theta_max         29.364
_diffrn_reflns_theta_min         2.276
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb 9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.444
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.20
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0328
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4734
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.0019217
_refine_ls_shift/su_mean         0.0004532
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 4.28P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1093
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1093
_reflns_limit_h_max              32
_reflns_limit_h_min              -32
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                4495
_reflns_number_total             4736
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.85
_oxford_diffrn_Wilson_scale      0.50
_oxford_refine_ls_r_factor_ref   0.0474
_oxford_refine_ls_scale          1.325(6)
_oxford_reflns_number_all        4734
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'Z:\kel1602SNM\Tony_kel1602SNM_da At 12: 1 on'
_cod_data_source_file            c8ob00865e2.cif
_cod_data_source_block           kel1602SNM
_cod_depositor_comments
'Adding full bibliography for 7156347--7156351.cif.'
_cod_original_sg_symbol_H-M      'C 1 2/c 1 '
_cod_database_code               7156349
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
SUMFIX ELEMENT SCALES 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,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) H   ( 172,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,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                                                                             
;