Diastereoselective Syntheses of Spiro[indoline-3,4'-pyridin]-2-yl)carbamates via AgOTf/Ph3P-Catalyzed Tandem Cyclizations of Tryptamine-Ynesulfonamides.
Liang, Guoduan; Pang, Yadong; Ji, Yanjun; Zhuang, Kaitong; Li, Linji; Xie, Fukai; Yang, Lu; Cheng, Maosheng; Lin, Bin; Liu, Yongxiang; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b02839

data_4037872
_publ_section_title
;
 Diastereoselective Syntheses of
 Spiro[indoline-3,4'-pyridin]-2-yl)carbamates via AgOTf/Ph3P-Catalyzed
 Tandem Cyclizations of Tryptamine-Ynesulfonamides.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02839
_journal_year                    2020
_chemical_formula_moiety         'C31 H34 Cl N3 O4 S'
_chemical_formula_sum            'C31 H34 Cl N3 O4 S'
_chemical_formula_weight         580.12
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.614(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.4939(5)
_cell_length_b                   25.4522(10)
_cell_length_c                   19.9319(9)
_cell_measurement_reflns_used    7810
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.1340
_cell_measurement_theta_min      2.5960
_cell_volume                     5803.0(4)
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -20.00   5.00   1.00    5.00    --  -11.59 -99.00 -30.00   25
  2  \w    -10.00  85.00   1.00    5.00    --   11.74  57.00 -90.00   95
  3  \w    -47.00  39.00   1.00    5.00    --   11.74 -77.00 120.00   86
;
_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      -0.0022800000
_diffrn_orient_matrix_UB_12      -0.0242203000
_diffrn_orient_matrix_UB_13      -0.0176975000
_diffrn_orient_matrix_UB_21      0.0088943000
_diffrn_orient_matrix_UB_22      -0.0137847000
_diffrn_orient_matrix_UB_23      0.0310212000
_diffrn_orient_matrix_UB_31      -0.0613083000
_diffrn_orient_matrix_UB_32      -0.0010954000
_diffrn_orient_matrix_UB_33      0.0015373000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27119
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.952
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76761
_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             2448
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     731
_refine_ls_number_reflns         10222
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0405P)^2^+1.8552P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1069
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8030
_reflns_number_total             10222
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02839_si_001.cif
_cod_data_source_block           sy0831
_cod_database_code               4037872
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.969
_reflns_odcompleteness_completeness 99.95
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C017(H017)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C01D(H01B,H01C), C12(H12A,H12B), C01I(H01D,H01E)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), N00F(H00F), C10(H10), C24(H24), C00V(H00V), C5(H5), C20(H20),
 C18(H18), C2(H2), C4(H4), C21(H21), C018(H018), C019(H019), C01A(H01A),
 C3(H3A), C14(H14), C01H(H01H), C15(H15), C17(H17), C01L(H01L), C01N(H01N),
 C23(H23), C01Q(H01Q), C01S(H01S), C01U(H01U), C01X(H01X), C01Z(H01Z),
 C020(H020)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C01W(H01F,H01G,H01I), C30(H30A,H30B,H30C), C021(H02A,
 H02B,H02C), C022(H02D,H02E,H02F), C31(H31A,H31B,H31C), C025(H02G,H02H,H02I),
 C29(H29A,H29B,H29C), C25(H25A,H25B,H25C), C028(H02J,H02K,H02L)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.279
_oxdiff_exptl_absorpt_empirical_full_min 0.825