Lewis Acid Catalyzed Cascade Reaction of 3-(2-Benzenesulfonamide)propargylic Alcohols to Spiro[indene-benzosultam]s.
Sun, Lang; Zhu, Yuanxun; Wang, Jing; Lu, Ping; Wang, Yanguang; Organic letters 17 (2015) 242–245; doi:10.1021/ol503316e

data_1518485
_publ_section_title
;
 Lewis Acid Catalyzed Cascade Reaction of
 3-(2-Benzenesulfonamide)propargylic Alcohols to
 Spiro[indene-benzosultam]s.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              242
_journal_page_last               245
_journal_paper_doi               10.1021/ol503316e
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C22 H16 I N O2 S'
_chemical_formula_sum            'C22 H16 I N O2 S'
_chemical_formula_weight         485.32
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-05-13
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.921(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0428(5)
_cell_length_b                   19.5870(8)
_cell_length_c                   12.8121(7)
_cell_measurement_reflns_used    2888
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5483
_cell_measurement_theta_min      2.8989
_cell_volume                     1950.29(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0622943000
_diffrn_orient_matrix_UB_12      -0.0101590000
_diffrn_orient_matrix_UB_13      -0.0474471000
_diffrn_orient_matrix_UB_21      -0.0396875000
_diffrn_orient_matrix_UB_22      0.0325184000
_diffrn_orient_matrix_UB_23      -0.0027894000
_diffrn_orient_matrix_UB_31      0.0537216000
_diffrn_orient_matrix_UB_32      0.0122466000
_diffrn_orient_matrix_UB_33      -0.0319618000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7709
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.90
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.766
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.847
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3570
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0299P)^2^+1.3711P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0818
_reflns_number_gt                2989
_reflns_number_total             3570
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol503316e_si_002.cif
_cod_data_source_block           140513_sl493_014
_cod_depositor_comments
'Adding full bibliography for 1518485--1518486.cif.'
_cod_original_cell_volume        1950.29(18)
_cod_database_code               1518485
_chemical_oxdiff_formula         'c10 h10 n2 o8 S1 i1'
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;