Rhodium(i)-catalysed cycloisomerisation/6π electrocyclisation of 5-(ethynylamino)pent-2-yn-1-yl esters to 2,3-dihydrobenzo[f]indoles
Merrett, James Theodore; Chen, Xiaoyu; Kyne, Sara Helen; Harode, Mandeep; Chan, Philip Wai Hong; New Journal of Chemistry 46 (2022) 13519–13523; doi:10.1039/D2NJ01992B

data_7061620
_publ_section_title
;
 Rhodium(i)-catalysed cycloisomerisation/6\p electrocyclisation of
 5-(ethynylamino)pent-2-yn-1-yl esters to 2,3-dihydrobenzo[f]indoles
;
_journal_issue                   28
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              13519
_journal_page_last               13523
_journal_paper_doi               10.1039/D2NJ01992B
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C28 H24 Cl N O4 S'
_chemical_formula_sum            'C28 H24 Cl N O4 S'
_chemical_formula_weight         505.99
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-07-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-15 deposited with the CCDC.	2022-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                98.270(3)
_cell_angle_beta                 94.546(3)
_cell_angle_gamma                114.109(3)
_cell_formula_units_Z            2
_cell_length_a                   9.8638(4)
_cell_length_b                   10.1729(3)
_cell_length_c                   13.2234(5)
_cell_measurement_reflns_used    4849
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      2
_cell_volume                     1184.47(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'XtaLAB Synergy Dualflex HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_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       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24865
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.473
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62171
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4849
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0589P)^2^+0.4490P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1103
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4138
_reflns_number_total             4849
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj01992b2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7061620.cif.'
_cod_database_code               7061620
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.932
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C11(H11A,H11B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C5(H5), C23(H23), C25(H25), C15(H15), C22(H22), C19(H19),
 C21(H21), C17(H17), C16(H16), C18(H18)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C28(H28A,H28B,H28C)
;
_olex2_submission_special_instructions 'No special instructions were received'