Photoinduced Cyclization of 3-Acyl-2-halo-1-[(ω-phenylethynyl)alkyl]indoles to Azaheterocyclo[1,2,3-lm]-Fused Benzo[c]carbazoles
Shenci Lu; Ren Wang; Yi Yang; Yang Li; Zongjun Shi; Wei Zhang; Zhifeng Tu; Journal of Organic Chemistry 76 (2011) 5661–5669; doi:10.1021/jo200630x

data_4026455
_publ_section_title
;
 Photoinduced Cyclization of
 3-Acyl-2-halo-1-[(\w-phenylethynyl)alkyl]indoles to
 Azaheterocyclo[1,2,3-lm]-Fused Benzo[c]carbazoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5661
_journal_page_last               5669
_journal_paper_doi               10.1021/jo200630x
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C19 H3.5 Br N'
_chemical_formula_weight         325.64
_chemical_name_systematic
; 
 ? 
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 103.675(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.216(4)
_cell_length_b                   12.671(5)
_cell_length_c                   12.559(5)
_cell_measurement_reflns_used    1565
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.49
_cell_measurement_theta_min      2.32
_cell_volume                     1425.0(10)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0520
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6667
_diffrn_reflns_theta_full        24.66
_diffrn_reflns_theta_max         24.66
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    2.875
_exptl_absorpt_correction_T_max  0.4328
_exptl_absorpt_correction_T_min  0.4080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_description       cubic
_exptl_crystal_F_000             638
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2395
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0540P)^2^+0.1162P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.1043
_reflns_number_gt                1638
_reflns_number_total             2395
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200630x_si_004.cif
_cod_data_source_block           p21c
_cod_original_formula_sum        'C19 H3.50 Br N'
_cod_database_code               4026455