Facile access to highly functionalized hydroisoquinoline deriva-tives via phosphine-catalyzed sequential [3 + 3]/[3 + 3] annulation
Huang, You; Li, Ning; Jia, Penghao; Chemical Communications  (2019) –; doi:10.1039/C9CC05832J

data_7124029
_publ_section_title
;
 Facile access to highly functionalized hydroisoquinoline deriva-tives via
 phosphine-catalyzed sequential [3 + 3]/[3 + 3] annulation
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC05832J
_journal_year                    2019
_chemical_formula_moiety         'C38 H33 N3 O4 S'
_chemical_formula_sum            'C38 H33 N3 O4 S'
_chemical_formula_weight         627.73
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc236bl8
_audit_creation_date             2019-07-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-23 deposited with the CCDC.    2019-08-19 downloaded from the CCDC.
;
_cell_angle_alpha                80.701(5)
_cell_angle_beta                 89.806(5)
_cell_angle_gamma                67.529(6)
_cell_formula_units_Z            2
_cell_length_a                   9.6639(6)
_cell_length_b                   9.6973(7)
_cell_length_c                   23.2323(13)
_cell_measurement_reflns_used    7127
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.5180
_cell_measurement_theta_min      1.7470
_cell_volume                     1981.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (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    'ShelXS-1997 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_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   -120.00  60.00   0.50    8.00    --  -30.00  45.00   0.00  360
  2  \w   -120.00  30.00   0.50    8.00    --  -30.00  45.00  90.00  300
  3  \w   -120.00  30.00   0.50    8.00    --  -30.00  45.00 180.00  300
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'rigaku xtalp200'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0088378000
_diffrn_orient_matrix_UB_12      0.0280112000
_diffrn_orient_matrix_UB_13      0.0267330000
_diffrn_orient_matrix_UB_21      -0.0784373000
_diffrn_orient_matrix_UB_22      0.0188939000
_diffrn_orient_matrix_UB_23      -0.0030204000
_diffrn_orient_matrix_UB_31      0.0102118000
_diffrn_orient_matrix_UB_32      -0.0729289000
_diffrn_orient_matrix_UB_33      0.0154127000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14630
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.020
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_min         1.780
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.052
_exptl_crystal_description       block
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         6836
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0833
_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^)+(0.1214P)^2^+1.2436P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2304
_refine_ls_wR_factor_ref         0.2404
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5337
_reflns_number_total             6836
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc05832j2.cif
_cod_data_source_block           m20180303b_sq
_cod_database_code               7124029
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.977
_reflns_odcompleteness_completeness 97.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Uiso/Uaniso restraints and constraints
Uanis(C38) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C16(H16), C17(H17), C18(H18)
3.b Secondary CH2 refined with riding coordinates:
 C37(H37A,H37B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C19(H19), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29),
  C31(H31), C32(H32), C33(H33), C34(H34), C35(H35)
3.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C38(H38A,H38B,H38C)
;
_shelx_res_checksum              59508
_shelx_fab_checksum              51436
_platon_squeeze_void_probe_radius 1.20
_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 1.618
_oxdiff_exptl_absorpt_empirical_full_min 0.444