One-pot total synthesis of streptindole, arsindoline B and their congeners through tandem decarboxylative deaminative dual-coupling reaction of amino acids with indoles.
Xiang, Jiachen; Wang, Jungang; Wang, Miao; Meng, Xianggao; Wu, Anxin; Organic & biomolecular chemistry 13 (2015) 4240–4247; doi:10.1039/c5ob00025d

data_7154346
_publ_section_title
;
 One-pot total synthesis of streptindole, arsindoline B and their
 congeners through tandem decarboxylative deaminative dual-coupling
 reaction of amino acids with indoles.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4240
_journal_page_last               4247
_journal_paper_doi               10.1039/c5ob00025d
_journal_volume                  13
_journal_year                    2015
_chemical_formula_sum            'C25 H22 N2'
_chemical_formula_weight         350.45
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-10-22 deposited with the CCDC.
2015-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.641(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4408(17)
_cell_length_b                   25.506(5)
_cell_length_c                   8.0660(15)
_cell_measurement_reflns_used    1801
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.44
_cell_measurement_theta_min      2.66
_cell_volume                     1932.9(6)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0446
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12169
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.17
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.9930
_exptl_absorpt_correction_T_min  0.9916
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_meas      1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0019(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3388
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.098
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0599P)^2^+0.2980P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1367
_reflns_number_gt                2132
_reflns_number_total             3388
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob00025d2.cif
_cod_data_source_block           e:\140304g\work\t
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/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 3008 2015-01-20 13:52:24Z robertas 

 Adding full bibliography for 7154346.cif.
;
_cod_original_cell_volume        1932.8(6)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7154346