Metal-Free [2 + 2 + 2] Cycloaddition of Ynamide-Nitriles with Ynamides: A Highly Regio- and Chemoselective Synthesis of δ-Carboline Derivatives.
Wen, Hao; Cao, Wei; Liu, Yu; Wang, Liang; Chen, Ping; Tang, Yu; The Journal of organic chemistry 83 (2018) 13308–13324; doi:10.1021/acs.joc.8b02112

data_4035719
_publ_section_title
;
 Metal-Free [2 + 2 + 2] Cycloaddition of Ynamide-Nitriles with Ynamides: A
 Highly Regio- and Chemoselective Synthesis of \d-Carboline Derivatives.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13308
_journal_page_last               13324
_journal_paper_doi               10.1021/acs.joc.8b02112
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C32 H24 N4 O4 S2'
_chemical_formula_sum            'C32 H24 N4 O4 S2'
_chemical_formula_weight         592.67
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-28
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                82.413(3)
_cell_angle_beta                 77.103(3)
_cell_angle_gamma                75.947(3)
_cell_formula_units_Z            2
_cell_length_a                   7.5067(19)
_cell_length_b                   12.180(3)
_cell_length_c                   16.789(4)
_cell_measurement_reflns_used    3464
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.114
_cell_measurement_theta_min      2.498
_cell_volume                     1446.6(6)
_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 0.995
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device_type  'Bruker SMART'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11762
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.714
_diffrn_reflns_theta_min         2.498
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.0343 before and 0.0302 after correction. The Ratio of minimum to maximum transmission is 0.9419. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         6214
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0449
_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^)+(0.0479P)^2^+0.4116P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1101
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4460
_reflns_number_total             6214
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02112_si_002.cif
_cod_data_source_block           hz45_0m
_cod_database_code               4035719
_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 Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C28(H28), C29(H29),
  C30(H30), C31(H31)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              56903
_shelx_hkl_checksum              48408
_olex2_submission_special_instructions 'No special instructions were received'