Assembly of indenamine derivatives through in situ formed N-sulfonyliminium ion initiated cyclization
Xiaohui Fan; Hao Lv; Yong-Hong Guan; Hong-Bo Zhu; Xiao-Meng Cui; Kun Guo; Chem.Commun. 50 (2014) 4119–; doi:10.1039/C4CC00310A

data_7112207
_publ_section_title
;
 Assembly of indenamine derivatives through in situ formed
 N-sulfonyliminium ion initiated cyclization
;
_journal_name_full               Chem.Commun.
_journal_page_first              4119
_journal_paper_doi               10.1039/C4CC00310A
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C21 H19 N O2 S'
_chemical_formula_sum            'C21 H19 N O2 S'
_chemical_formula_weight         349.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-08-02
_audit_creation_method
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  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2086(5)
_cell_length_b                   7.3342(6)
_cell_length_c                   23.4547(12)
_cell_measurement_reflns_used    1069
_cell_measurement_temperature    301.19(10)
_cell_measurement_theta_max      24.6620
_cell_measurement_theta_min      3.8230
_cell_volume                     1756.10(19)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      301.19(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9962
_diffrn_measured_fraction_theta_max 0.6027
_diffrn_measurement_details
;
  1 omega   35.00   93.50   1.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  178.0000  150.0000 39

  2 omega   37.00   73.00   1.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   38.0000 -150.0000 24

  3 omega  -35.00   35.50   1.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -57.0000  -90.0000 47
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0019727000
_diffrn_orient_matrix_UB_12      -0.0023889000
_diffrn_orient_matrix_UB_13      -0.0302195000
_diffrn_orient_matrix_UB_21      -0.0595286000
_diffrn_orient_matrix_UB_22      -0.0496444000
_diffrn_orient_matrix_UB_23      0.0011092000
_diffrn_orient_matrix_UB_31      -0.0357436000
_diffrn_orient_matrix_UB_32      0.0828884000
_diffrn_orient_matrix_UB_33      -0.0001900000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0689
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            4431
_diffrn_reflns_point_group_measured_fraction_full 0.690
_diffrn_reflns_point_group_measured_fraction_max 0.686
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         3.420
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 377 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.15(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2372
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0238P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0909
_reflns_Friedel_coverage         0.339
_reflns_Friedel_fraction_full    0.366
_reflns_Friedel_fraction_max     0.356
_reflns_number_gt                1700
_reflns_number_total             2372
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc00310a2.cif
_cod_data_source_block           fanxh0802
_cod_original_cell_volume        1756.09(19)
_cod_database_code               7112207
_reflns_odcompleteness_completeness 99.62
_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.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C19(H19), C17(H17), C20(H20), C4(H4), C1(H1), C2(H2), C7(H7),
 C8(H8), C3(H3A)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C21(H21A,H21B,H21C)
;
_shelx_hkl_checksum              46044
_shelx_res_checksum              78170
_shelxl_version_number           2013-2