Silver-Catalyzed 1,3-Acyloxy Migration/Diels-Alder Reaction of 1,9-Dien-4-yne Esters to Partially Hydrogenated Isoquinolines.
Zhao, Yichao; Jin, Jianwen; Boyle, Joshua William; Lee, Bo Ra; Day, David Philip; Susanti, Dewi; Clarkson, Guy James; Chan, Philip Wai Hong; The Journal of organic chemistry 82 (2017) 2826–2834; doi:10.1021/acs.joc.7b00048

data_4032344
_publ_section_title
;
 Silver-Catalyzed 1,3-Acyloxy Migration/Diels-Alder Reaction of
 1,9-Dien-4-yne Esters to Partially Hydrogenated Isoquinolines.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2826
_journal_page_last               2834
_journal_paper_doi               10.1021/acs.joc.7b00048
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C25 H27 N O4 S'
_chemical_formula_sum            'C25 H27 N O4 S'
_chemical_formula_weight         437.53
_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             2017-01-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3368 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.9332(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.21961(4)
_cell_length_b                   11.09937(5)
_cell_length_c                   18.19019(7)
_cell_measurement_reflns_used    30279
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.4980
_cell_measurement_theta_min      3.9530
_cell_volume                     2188.731(16)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9998
_diffrn_measured_fraction_theta_max 0.9575
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -118.00  -9.00   1.00    1.00    --  -41.82 -77.00 150.00  109
  2  \w    -66.00  33.00   1.00    1.00    --  -41.82  37.00-180.00   99
  3  \w   -114.00 -14.00   1.00    1.00    --  -41.82 -57.00-150.00  100
  4  \w   -122.00  -1.00   1.00    1.00    --  -41.82 -19.00   0.00  121
  5  \w   -114.00 -14.00   1.00    1.00    --  -41.82 -57.00-180.00  100
  6  \w     23.00  98.00   1.00    1.00    --   41.82-125.00-180.00   75
  7  \w     17.00 116.00   1.00    1.00    --   41.82  37.00-180.00   99
  8  \w     78.00 178.00   1.00    4.00    --  107.00  61.00-120.00  100
  9  \w     74.00 178.00   1.00    4.00    --  107.00  77.00-150.00  104
 10  \w     78.00 178.00   1.00    4.00    --  107.00  61.00 120.00  100
 11  \w     81.00 178.00   1.00    4.00    --  107.00  45.00 -90.00   97
 12  \w     94.00 178.00   1.00    4.00    --  107.00 125.00  60.00   84
 13  \w     74.00 178.00   1.00    4.00    --  107.00  77.00 120.00  104
 14  \w     94.00 178.00   1.00    4.00    --  107.00 125.00 -60.00   84
 15  \w     34.00 121.00   1.00    4.00    --  107.00-125.00 -90.00   87
 16  \w     74.00 178.00   1.00    4.00    --  107.00  77.00-180.00  104
 17  \w     78.00 178.00   1.00    4.00    --  107.00  61.00-150.00  100
 18  \w     74.00 178.00   1.00    4.00    --  107.00  77.00-120.00  104
 19  \w     34.00 121.00   1.00    4.00    --  107.00-125.00-120.00   87
 20  \w     78.00 178.00   1.00    4.00    --  107.00  61.00 150.00  100
 21  \w     81.00 178.00   1.00    4.00    --  107.00  45.00-150.00   97
 22  \w     74.00 178.00   1.00    4.00    --  107.00  77.00 150.00  104
 23  \w     81.00 178.00   1.00    4.00    --  107.00  45.00 150.00   97
 24  \w     78.00 178.00   1.00    4.00    --  107.00  61.00-180.00  100
 25  \w     81.00 178.00   1.00    4.00    --  107.00  45.00-180.00   97
 26  \w     81.00 178.00   1.00    4.00    --  107.00  45.00  30.00   97
 27  \w     81.00 178.00   1.00    4.00    --  107.00  45.00-120.00   97
 28  \w     94.00 178.00   1.00    4.00    --  107.00 125.00 -90.00   84
 29  \w     79.00 178.00   1.00    4.00    --  107.00  30.00-180.00   99
 30  \w     94.00 178.00   1.00    4.00    --  107.00 125.00  30.00   84
 31  \w   -118.00 -61.00   1.00    1.00    --  -41.82 -77.00 -30.00   57
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0500743000
_diffrn_orient_matrix_UB_12      0.0441278000
_diffrn_orient_matrix_UB_13      0.0825085000
_diffrn_orient_matrix_UB_21      -0.1327537000
_diffrn_orient_matrix_UB_22      0.0091622000
_diffrn_orient_matrix_UB_23      0.0085796000
_diffrn_orient_matrix_UB_31      0.0075342000
_diffrn_orient_matrix_UB_32      -0.1312798000
_diffrn_orient_matrix_UB_33      0.0283351000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            39823
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.665
_diffrn_reflns_theta_min         4.078
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.576
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.328
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4413
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0658P)^2^+0.7879P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1106
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4356
_reflns_number_total             4413
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00048_si_005.cif
_cod_data_source_block           sh4
_cod_depositor_comments          'Adding full bibliography for 4032344.cif.'
_cod_original_cell_volume        2188.730(15)
_cod_database_code               4032344
_chemical_oxdiff_formula         'C20 H20 N2 O2 S'
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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 Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B), C18(H18A,H18B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C14(H14), C24(H24), C25(H25), C26(H26),
 C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              93240
_shelx_hkl_checksum              45048
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.148
_oxdiff_exptl_absorpt_empirical_full_min 0.501