Intramolecular rhodium-catalysed [2 + 2 + 2] cycloaddition of linear chiral N-bridged triynes: straightforward access to fused tetrahydroisoquinoline core
Llobat, Alberto; Escorihuela, Jorge; Ramírez de Arellano, Carmen; Fustero, Santos; Medio-Simón, Mercedes; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00340F

data_7158569
_publ_section_title
;
 Intramolecular rhodium-catalysed [2 + 2 + 2] cycloaddition of linear
 chiral N-bridged triynes: straightforward access to fused
 tetrahydroisoquinoline core
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00340F
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_sum            'C153 H106 Cl2 F40 N8 O16 S8'
_chemical_formula_weight         3399.83
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-07-29 deposited with the CCDC.	2022-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   7.7647(5)
_cell_length_b                   12.5408(11)
_cell_length_c                   38.014(3)
_cell_measurement_reflns_used    9938
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.50
_cell_measurement_theta_min      2.68
_cell_volume                     3701.6(5)
_computing_cell_refinement       'Bruker, APEX3 v2019.11'
_computing_data_collection       'Bruker, APEX3 v2019.11'
_computing_data_reduction        'Bruker, APEX3 v2019.11'
_computing_molecular_graphics    'CrystalMaker v9.2, 2017'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0451
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            127114
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        29.717
_diffrn_reflns_theta_max         29.717
_diffrn_reflns_theta_min         2.677
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2, Bruker-AXS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_description       spike
_exptl_crystal_F_000             1730
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details
; 
 Flack x determined using 3767 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.033(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     562
_refine_ls_number_reflns         10449
_refine_ls_number_restraints     58
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0523
_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^)+(0.0635P)^2^+3.0666P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1371
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                9811
_reflns_number_total             10449
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00340f2.cif
_cod_data_source_block           MM_aln459
_cod_database_code               7158569
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              33868