Pseudopericyclic 1,5- versus Pericyclic 1,4- and 1,6-Electrocyclization in Electron-Poor 4-Aryl-2-azabuta-1,3-dienes: Indole Synthesis from 2H-Azirines and Diazo Compounds.
Novikov, Mikhail S.; Khlebnikov, Alexander F.; Rostovskii, Nikolai V.; Tcyrulnikov, Sergei; Suhanova, Anna A.; Zavyalov, Kirill V.; Yufit, Dmitry S.; The Journal of organic chemistry 80 (2014) 18–; doi:10.1021/jo501051n

data_4030325
_publ_section_title
;
 Pseudopericyclic 1,5- versus Pericyclic 1,4- and 1,6-Electrocyclization
 in Electron-Poor 4-Aryl-2-azabuta-1,3-dienes: Indole Synthesis from
 2H-Azirines and Diazo Compounds.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              18
_journal_paper_doi               10.1021/jo501051n
_journal_volume                  80
_journal_year                    2014
_chemical_formula_moiety         'C25 H21 N O4'
_chemical_formula_sum            'C25 H21 N O4'
_chemical_formula_weight         399.43
_chemical_melting_point          449.6(15)
_chemical_name_systematic
;
Dimethyl 2-(2,3-diphenyl-1H-indol-1-yl)malonate 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-05-28
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.8984(4)
_cell_length_b                   12.9658(3)
_cell_length_c                   19.5357(5)
_cell_measurement_reflns_used    8520
_cell_measurement_temperature    120
_cell_measurement_theta_max      25.63
_cell_measurement_theta_min      2.28
_cell_volume                     4027.00(17)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            63105
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.08
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           10.0
_diffrn_source_power             0.3
_diffrn_source_target            Mo
_diffrn_source_voltage           30.0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6438
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2006/1 (Bruker,2006) was used for absorption correction.
R(int) was 0.0433 before and 0.0336 after correction.
The Ratio of minimum to maximum transmission is 0.6438.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         5346
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+2.7000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.1109
_reflns_number_gt                3672
_reflns_number_total             5346
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501051n_si_002.cif
_cod_data_source_block           6a_dax53
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '175-178C' was changed to '449.6(15)'
- it was converted from degrees Celsius(C) to Kelvins(K), the average
value was taken and precision was estimated.

'_diffrn_source_target'
value 'MO' changed to 'Mo' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 4030324--4030325.cif.
;
_cod_database_code               4030325