One Pot Hydroamination/[4+3] Cycloaddition: Synthesis towards the Cyclohepta[b]indole Core of Silicine and Ervatamine
XUE, Jijun; Zhang, Jie; Shao, Jidong; Wang, Yongxiang; Li, Ying; RSC Adv.  (2014) –; doi:10.1039/C4RA13249A

data_7218823
_publ_section_title
;
 One Pot Hydroamination/[4+3] Cycloaddition: Synthesis towards the
 Cyclohepta[b]indole Core of Silicine and Ervatamine
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA13249A
_journal_year                    2014
_chemical_formula_moiety         'C23 H22 F N O3 S'
_chemical_formula_sum            'C23 H22 F N O3 S'
_chemical_formula_weight         411.47
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-05-07
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.1688(16)
_cell_length_b                   8.5376(4)
_cell_length_c                   20.5949(12)
_cell_measurement_reflns_used    2210
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.7300
_cell_measurement_theta_min      3.6810
_cell_volume                     4073.8(4)
_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    '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(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0168361000
_diffrn_orient_matrix_UB_12      0.0575424000
_diffrn_orient_matrix_UB_13      0.0160862000
_diffrn_orient_matrix_UB_21      -0.0200440000
_diffrn_orient_matrix_UB_22      0.0585267000
_diffrn_orient_matrix_UB_23      -0.0094151000
_diffrn_orient_matrix_UB_31      -0.0158624000
_diffrn_orient_matrix_UB_32      -0.0129144000
_diffrn_orient_matrix_UB_33      0.0289671000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13772
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         3.125
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55932
_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 colourless'
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4002
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.1263
_refine_ls_R_factor_gt           0.0734
_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^)+(0.0833P)^2^+2.3392P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1787
_refine_ls_wR_factor_ref         0.2196
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2259
_reflns_number_total             4002
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ra13249a2.cif
_cod_data_source_block           zhangjie0507
_cod_database_code               7218823
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.36
_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(C5) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C2) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C5(H5)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C10(H10), C11(H11), C13(H13), C18(H18), C19(H19), C21(H21),
 C22(H22)
3.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              19381
_shelx_hkl_checksum              53557