An atmosphere and light tuned highly diastereoselective synthesis of cyclobuta/penta[b]indoles from aniline-tethered alkylidenecyclopropanes with alkynes.
Cao, Bo; Wei, Yin; Shi, Min; Chemical communications (Cambridge, England) 54 (2018) 2870–2873; doi:10.1039/c8cc00180d

data_7121287
_publ_section_title
;
 An atmosphere and light tuned highly diastereoselective synthesis of
 cyclobuta/penta[b]indoles from aniline-tethered alkylidenecyclopropanes
 with alkynes.
;
_journal_issue                   23
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2870
_journal_page_last               2873
_journal_paper_doi               10.1039/c8cc00180d
_journal_volume                  54
_journal_year                    2018
_chemical_formula_sum            'C28 H22 Br Cl N2 O2'
_chemical_formula_weight         533.83
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-10-12 deposited with the CCDC.
2018-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.440(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   32.328(10)
_cell_length_b                   10.078(3)
_cell_length_c                   15.161(4)
_cell_measurement_reflns_used    9896
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      53.883
_cell_measurement_theta_min      5.345
_cell_volume                     4658(2)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            38239
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.434
_exptl_absorpt_coefficient_mu    1.910
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.00054(17)
_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   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4570
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0357P)^2^+13.6395P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1239
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3545
_reflns_number_total             4570
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc00180d2.cif
_cod_data_source_block           mo_d8v17426_0m
_cod_depositor_comments
'Adding full bibliography for 7121284--7121288.cif.'
_cod_database_code               7121287
_shelx_estimated_absorpt_t_min   0.737
_shelx_estimated_absorpt_t_max   0.803
_shelxl_version_number           2013-4
_shelx_res_checksum              83897