Rapid Cascade Synthesis of Poly-Heterocyclic Architectures from Indigo
Alireza Shakoori; John B. Bremner; Anthony C. Willis; Rachada Haritakun; Paul A. Keller; Journal of Organic Chemistry 78 (2013) 7639–7647; doi:10.1021/jo401210r

data_4028472
_publ_contact_author_address
;
Research School of Chemistry,
The Australian National University,
Canberra, A. C. T. 0200, Australia
;
_publ_contact_author_email       ' willis@rsc.anu.edu.au '
_publ_contact_author_fax         ' 61 2 6125 0750 '
_publ_contact_author_name        ' Anthony C. Willis '
_publ_contact_author_phone       ' 61 2 6125 4109 '
_publ_section_title
;
 Rapid Cascade Synthesis of Poly-Heterocyclic Architectures from Indigo
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7639
_journal_page_last               7647
_journal_paper_doi               10.1021/jo401210r
_journal_volume                  78
_journal_year                    2013
_chemical_compound_source        ' from U of Wollongong'
_chemical_formula_moiety         'C25 H16 N2 O2'
_chemical_formula_sum            'C25 H16 N2 O2'
_chemical_formula_weight         376.41
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             12-08-16
_audit_creation_method           CRYSTALS_ver_14.11
_audit_update_record
;
2012-08-16 - Report on C25 H16 N2 O2
             by Anthony C. Willis
             for Paul Keller

2012-08-16 - passes checkcif tests with minor warnings  
;
_cell_angle_alpha                90
_cell_angle_beta                 106.0180(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8893(2)
_cell_length_b                   21.6743(4)
_cell_length_c                   10.0894(2)
_cell_measurement_reflns_used    22246
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     1868.45(7)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
; 
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_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      200
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ' \f and \w scans with CCD '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            36338
_diffrn_reflns_theta_full        27.496
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.819
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.28
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.9556
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4287
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.0004522
_refine_ls_shift/su_mean         0.0000833
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.40P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0981
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0981
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              28
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                3143
_reflns_number_total             4287
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.07
_oxford_diffrn_Wilson_scale      2.87
_oxford_refine_ls_r_factor_ref   0.0625
_oxford_refine_ls_scale          0.6112(12)
_oxford_reflns_number_all        4287
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '8161523 kel1206'
_cod_data_source_file            jo401210r_si_003.cif
_cod_data_source_block           cmpd7
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               4028472
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'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   (   6,X'S) H   (  61,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) H   ( 272,X'S) 
RIDE C   (  29,X'S) H   ( 291,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                                                                             
;