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_7121286
_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_moiety         'C24 H24 Br N O4'
_chemical_formula_sum            'C24 H24 Br N O4'
_chemical_formula_weight         470.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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     dual
_audit_creation_date             2016-12-15
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2016-12-15 deposited with the CCDC.
2018-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.809(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8749(12)
_cell_length_b                   13.1162(14)
_cell_length_c                   14.6639(16)
_cell_measurement_reflns_used    3164
_cell_measurement_temperature    130
_cell_measurement_theta_max      25.069
_cell_measurement_theta_min      2.37
_cell_volume                     2186.4(4)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_unetI/netI     0.0721
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21906
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.640
_diffrn_reflns_theta_min         1.791
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.910
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0884 before and 0.0441 after correction.
The Ratio of minimum to maximum transmission is 0.7689.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.863
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         6683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0461
_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^)+(0.0472P)^2^+0.5140P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1120
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4120
_reflns_number_total             6683
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc00180d2.cif
_cod_data_source_block           mo_dm16863_0m
_cod_depositor_comments
'Adding full bibliography for 7121284--7121288.cif.'
_cod_database_code               7121286
_shelx_estimated_absorpt_t_max   0.911
_shelx_estimated_absorpt_t_min   0.763
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C20(H20A,H20B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C16(H16),
 C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              87805
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'