Iodine-Mediated Solvent-Controlled Selective Electrophilic Cyclization and Oxidative Esterification ofo-Alkynyl Aldehydes: An Easy Access to Pyranoquinolines, Pyranoquinolinones, and Isocumarins
Akhilesh K. Verma; Vineeta Rustagi; Trapti Aggarwal; Amit P. Singh; Journal of Organic Chemistry 75 (2010) 7691–7703; doi:10.1021/jo101526b

data_4025819
_publ_section_title
;
 Iodine-Mediated Solvent-Controlled Selective Electrophilic Cyclization
 and Oxidative Esterification ofo-Alkynyl Aldehydes: An Easy Access to
 Pyranoquinolines, Pyranoquinolinones, and Isocumarins
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7691
_journal_page_last               7703
_journal_paper_doi               10.1021/jo101526b
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C22 H18 I N O2'
_chemical_formula_sum            'C22 H18 I N O2'
_chemical_formula_weight         455.27
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.85(3)
_cell_angle_beta                 99.30(3)
_cell_angle_gamma                103.80(3)
_cell_formula_units_Z            2
_cell_length_a                   5.905(2)
_cell_length_b                   10.998(4)
_cell_length_c                   15.103(5)
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      0.841
_cell_measurement_theta_min      0.813
_cell_volume                     934.3(6)
_computing_cell_refinement
;CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.49b (release 14-10-2009 CrysAlis171 .NET)
(compiled Oct 14 2009,10:37:23)
;
_computing_data_collection
;CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.49b (release 14-10-2009 CrysAlis171 .NET)
(compiled Oct 14 2009,10:37:23)
;
_computing_data_reduction        'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 15.9853
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0716
_diffrn_reflns_av_sigmaI/netI    0.0726
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6638
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         3.18
_exptl_absorpt_coefficient_mu    1.729
_exptl_absorpt_correction_T_max  0.841
_exptl_absorpt_correction_T_min  0.813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.49b (release 14-10-2009 CrysAlis171 .NET)
(compiled Oct 14 2009,10:37:23)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.465
_refine_diff_density_min         -2.504
_refine_diff_density_rms         0.185
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3862
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0673
_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^)+(0.1213P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1711
_refine_ls_wR_factor_ref         0.1806
_reflns_number_gt                2952
_reflns_number_total             3862
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101526b_si_003.cif
_cod_data_source_block           tag-146
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        934.4(6)
_cod_original_sg_symbol_Hall     -P1
_cod_database_code               4025819