Stereoselective and regioselective 5-exo-dig cyclization of 8-alkynylnaphthalen-1-amines for the synthesis of (E)-2-(arylthio)alkylene-1,2-dihydrobenzo[cd]indoles.
Bi, Cheng; Zhang, Lianpeng; Qiu, Guanyinsheng; Li, Xiaofang; Yao, Jinzhong; Zhou, Hongwei; Organic & biomolecular chemistry 16 (2018) 3006–3011; doi:10.1039/c8ob00556g

data_7156180
_publ_section_title
;
 Stereoselective and regioselective 5-exo-dig cyclization of
 8-alkynylnaphthalen-1-amines for the synthesis of
 (E)-2-(arylthio)alkylene-1,2-dihydrobenzo[cd]indoles.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3006
_journal_page_last               3011
_journal_paper_doi               10.1039/c8ob00556g
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C31 H21 Br Cl N O2 S2, C H Cl3'
_chemical_formula_sum            'C32 H22 Br Cl4 N O2 S2'
_chemical_formula_weight         738.33
_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             2017-02-17
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.02.06 svn.r3384 for OlexSys, GUI svn.r5312)
;
_audit_update_record
;
2017-12-20 deposited with the CCDC.
2018-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.634(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9316(14)
_cell_length_b                   9.6118(13)
_cell_length_c                   33.373(5)
_cell_measurement_reflns_used    9896
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.185
_cell_measurement_theta_min      2.263
_cell_volume                     3157.6(8)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0494
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            46965
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.556
_diffrn_reflns_theta_min         2.069
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.804
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1115 before and 0.0547 after correction. The Ratio of minimum to maximum transmission is 0.7230. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.672
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         7276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0507
_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^)+(0.0780P)^2^+2.6160P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1527
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5095
_reflns_number_total             7276
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00556g3.cif
_cod_data_source_block           mo_2017038_0m
_cod_depositor_comments          'Adding full bibliography for 7156180.cif.'
_cod_original_cell_volume        3157.5(8)
_cod_database_code               7156180
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C32(H32)
2.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C15(H15), C25(H25), C31(H31), C22(H22), C24(H24), C9(H9), C27(H27),
 C30(H30), C28(H28), C6(H6), C14(H14), C7(H7), C10(H10), C13(H13), C4(H4),
 C11(H11), C3(H3)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'