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_7112206
_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      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   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-07-30
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                97.496(15)
_cell_angle_beta                 111.360(17)
_cell_angle_gamma                90.383(14)
_cell_formula_units_Z            2
_cell_length_a                   8.5924(14)
_cell_length_b                   10.4758(18)
_cell_length_c                   10.797(2)
_cell_measurement_reflns_used    1909
_cell_measurement_temperature    293.80(10)
_cell_measurement_theta_max      26.7220
_cell_measurement_theta_min      3.8150
_cell_volume                     895.8(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
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      293.80(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9964
_diffrn_measured_fraction_theta_max 0.8762
_diffrn_measurement_details
;
  1 omega  -17.00   25.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  -99.0000 -120.0000 28

  2 omega   19.00   50.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700   57.0000 -120.0000 21

  3 omega  -88.00  -17.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  -77.0000 -150.0000 47

  4 omega  -45.00   48.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -57.0000  -30.0000 62

  5 omega   50.00   84.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  178.0000    0.0000 23

  6 omega   36.00   61.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -99.0000  120.0000 17

  7 omega    0.00   93.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   57.0000  120.0000 62
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0517428000
_diffrn_orient_matrix_UB_12      -0.0538248000
_diffrn_orient_matrix_UB_13      -0.0417687000
_diffrn_orient_matrix_UB_21      0.0319318000
_diffrn_orient_matrix_UB_22      -0.0378040000
_diffrn_orient_matrix_UB_23      0.0528606000
_diffrn_orient_matrix_UB_31      -0.0647661000
_diffrn_orient_matrix_UB_32      0.0188946000
_diffrn_orient_matrix_UB_33      0.0234057000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5643
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         3.19
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
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 light yellow'
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.3600
_exptl_crystal_size_mid          0.3400
_exptl_crystal_size_min          0.2800
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3519
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0566
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0522P)^2^+0.4006P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1524
_reflns_number_gt                2622
_reflns_number_total             3519
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc00310a2.cif
_cod_data_source_block           fanxh0725_1
_cod_database_code               7112206
_reflns_odcompleteness_completeness 99.64
_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. Uiso/Uaniso restraints and constraints
Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C13(H13)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C11(H11), C16(H16), C17(H17),
 C19(H19), C20(H20)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C21(H21A,H21B,H21C)
;