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_4026454
_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 H14 Cl N'
_chemical_formula_weight         291.76
_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                 108.051(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.161(8)
_cell_length_b                   4.746(2)
_cell_length_c                   20.732(10)
_cell_measurement_reflns_used    397
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.17
_cell_measurement_theta_min      2.83
_cell_volume                     1418.3(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      296(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_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  0.0597
_diffrn_reflns_av_sigmaI/netI    0.0971
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            4881
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_T_max  0.9235
_exptl_absorpt_correction_T_min  0.9142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0048(11)
_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   0.924
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2509
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.924
_refine_ls_R_factor_all          0.1413
_refine_ls_R_factor_gt           0.0542
_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^)+(0.0477P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1361
_reflns_number_gt                1124
_reflns_number_total             2509
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200630x_si_003.cif
_cod_data_source_block           p21c
_cod_original_cell_volume        1418.2(12)
_cod_database_code               4026454