Thermal Cycloisomerization of Putative Allenylpyridines for the Synthesis of Isoquinoline Derivatives.
Morrison, Alec E.; Hrudka, Jeremy J.; Dudley, Gregory B.; Organic letters 18 (2016) 4104–4107; doi:10.1021/acs.orglett.6b02034

data_1555676
_publ_section_title
;
 Thermal Cycloisomerization of Putative Allenylpyridines for the Synthesis
 of Isoquinoline Derivatives.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4104
_journal_page_last               4107
_journal_paper_doi               10.1021/acs.orglett.6b02034
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C23 H25 N'
_chemical_formula_weight         315.44
_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_method           SHELXL-2013
_cell_angle_alpha                75.115(3)
_cell_angle_beta                 77.430(3)
_cell_angle_gamma                81.256(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1533(15)
_cell_length_b                   10.925(2)
_cell_length_c                   12.115(3)
_cell_measurement_reflns_used    755
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      26.23
_cell_measurement_theta_min      2.30
_cell_volume                     888.4(3)
_computing_cell_refinement       'SMART V5.625 (Bruker, 2000)'
_computing_data_collection       'SMART V5.625 (Bruker, 2000)'
_computing_data_reduction        'SAINT V6.32 (Bruker, 2001)'
_computing_molecular_graphics    'SHELXL-2013 (Sheldrick, 2013)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measurement_device_type  'Bruker APEX II CCD area-detector'
_diffrn_measurement_method       'profile data from \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7111
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.213
_diffrn_reflns_theta_min         1.770
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.03 (Bruker, 2003)'
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3908
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1067
_refine_ls_R_factor_gt           0.0570
_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^)+(0.1097P)^2^+0.0257P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1558
_refine_ls_wR_factor_ref         0.1898
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2417
_reflns_number_total             3908
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02034_si_002.cif
_cod_data_source_block           aem1
_cod_database_code               1555676
_shelx_estimated_absorpt_t_min   0.992
_shelx_estimated_absorpt_t_max   0.998
_shelxl_version_number           2013-4
_shelx_res_checksum              12624
_shelx_hkl_checksum              9626