The mechanism of N-vinylindole formation via tandem imine formation and cycloisomerisation of o-ethynylanilines
Kennedy, Danielle F.; Nova, Ainara; Willis, Anthony C.; Eisenstein, Odile; Messerle, Barbara A.; Dalton Transactions  (2009) 10296–10304; doi:10.1039/b915269e

data_7002847
_publ_section_title
;
 The mechanism of N-vinylindole formation via tandem imine formation
 and cycloisomerisation of o-ethynylanilines
;
_journal_issue                   46
_journal_name_full               'Dalton Transactions'
_journal_page_first              10296
_journal_page_last               10304
_journal_paper_doi               10.1039/b915269e
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_compound_source        ' from UNSW'
_chemical_formula_moiety         'C24 H26 Cl2 Ir N, C H2 Cl2'
_chemical_formula_sum            'C25 H28 Cl4 Ir N'
_chemical_formula_weight         676.53
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             06-07-03
_audit_creation_method           CRYSTALS_ver_12.18
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8981(1)
_cell_length_b                   11.8148(2)
_cell_length_c                   24.1539(3)
_cell_measurement_reflns_used    30440
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3
_cell_volume                     2539.28(6)
_computing_cell_refinement       'Denzo/Scalepack '
_computing_data_collection       'COLLECT (Nonius BV, 1997)'
_computing_data_reduction        'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_computing_publication_material  'CRYSTALS '
_computing_structure_refinement  'CRYSTALS (Watkin 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_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  0.028
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            29393
_diffrn_reflns_theta_full        27.516
_diffrn_reflns_theta_max         27.516
_diffrn_reflns_theta_min         2.843
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.692
_exptl_absorpt_correction_T_max  0.661
_exptl_absorpt_correction_T_min  0.367
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.770
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.79
_refine_diff_density_min         -1.00
_refine_ls_abs_structure_details 'Flack (1983), 2523 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.019(4)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9414
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         5819
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0177
_refine_ls_R_factor_gt           0.0163
_refine_ls_shift/su_max          0.002348
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
11.3 13.6 4.60
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0302
_refine_ls_wR_factor_gt          0.0291
_refine_ls_wR_factor_ref         0.0302
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              31
_reflns_limit_l_min              0
_reflns_number_gt                5566
_reflns_number_total             5831
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.95
_oxford_diffrn_Wilson_scale      16.93
_oxford_refine_ls_scale          0.31884(7)
_oxford_structure_analysis_title '7031225 nsw0616'
_cod_data_source_file            b915269e.txt
_cod_data_source_block           nsw0616
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               7002847