Divergent reactions of indoles with aminobenzaldehydes: indole ring-opening vs. annulation and facile synthesis of neocryptolepine
Vecchione, Matthew K.; Sun, Aaron X.; Seidel, Daniel; Chemical Science 2 (2011) 2178–; doi:10.1039/c1sc00506e

data_1515568
_publ_section_title
;
 Divergent reactions of indoles with aminobenzaldehydes: indole
 ring-opening vs. annulation and facile synthesis of neocryptolepine
;
_journal_issue                   11
_journal_name_full               'Chemical Science'
_journal_page_first              2178
_journal_paper_doi               10.1039/c1sc00506e
_journal_volume                  2
_journal_year                    2011
_chemical_formula_sum            'C16 H12 N2'
_chemical_formula_weight         232.28
_space_group_IT_number           15
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.058(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   54.319(8)
_cell_length_b                   4.7958(7)
_cell_length_c                   18.476(3)
_cell_measurement_reflns_used    5212
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.41
_cell_measurement_theta_min      2.35
_cell_volume                     4549.2(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \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  0.0670
_diffrn_reflns_av_sigmaI/netI    0.0548
_diffrn_reflns_limit_h_max       62
_diffrn_reflns_limit_h_min       -62
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14989
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9976
_exptl_absorpt_correction_T_min  0.9690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SAINT (SADABS)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         3886
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0629
_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^)+(0.0790P)^2^+7.9000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1558
_refine_ls_wR_factor_ref         0.1676
_reflns_number_gt                2946
_reflns_number_total             3886
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1sc00506e.txt
_cod_data_source_block           aaron001
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        4549.2(11)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1515568