Preparation of 3-aryl-2-aminoindoles, 3-allyl-3-amino-2-iminoindolines, and tetrahydro-[1,4]diazepino[2,3-b]indoles from 3-diazoindolin-2-imines
Guorong Sheng; Kai Huang; Shicong Ma; Jing Qian; Ping Lu; Yanguang Wang; Chem.Commun. 51 (2015) 11056–; doi:10.1039/C5cc03238E

data_7117393
_publ_section_title
;
 Preparation of 3-aryl-2-aminoindoles, 3-allyl-3-amino-2-iminoindolines,
 and tetrahydro-[1,4]diazepino[2,3-b]indoles from 3-diazoindolin-2-imines
;
_journal_name_full               Chem.Commun.
_journal_page_first              11056
_journal_paper_doi               10.1039/C5cc03238E
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C27 H27 N3 O2 S'
_chemical_formula_sum            'C27 H27 N3 O2 S'
_chemical_formula_weight         457.58
_chemical_melting_point          520.6(5)
_chemical_name_systematic
2,6-dimethyl-1-phenyl-4-(tosylmethyl)-1,2,3,6-tetrahydro-[1,4]diazepino[2,3-b]indole
_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             2014-10-17
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2014-12-29 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.689(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0312(4)
_cell_length_b                   13.3378(5)
_cell_length_c                   19.5264(8)
_cell_measurement_reflns_used    3872
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4435
_cell_measurement_theta_min      2.8377
_cell_volume                     2318.53(17)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0331161000
_diffrn_orient_matrix_UB_12      -0.0012604000
_diffrn_orient_matrix_UB_13      -0.0356027000
_diffrn_orient_matrix_UB_21      -0.0115707000
_diffrn_orient_matrix_UB_22      0.0525705000
_diffrn_orient_matrix_UB_23      0.0005741000
_diffrn_orient_matrix_UB_31      0.0715469000
_diffrn_orient_matrix_UB_32      0.0079414000
_diffrn_orient_matrix_UB_33      -0.0094738000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15422
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.84
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55617
_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            yellow
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             968
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: HE/EA'
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4234
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0592P)^2^+0.3702P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1268
_reflns_number_gt                3208
_reflns_number_total             4234
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc03238e2.cif
_cod_data_source_block           141016_sgr2_163b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '520.15-521.15' was changed to
'520.6(5)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 3392 2015-05-12 13:50:21Z andrius 
;
_cod_original_cell_volume        2318.54(17)
_cod_database_code               7117393
_chemical_oxdiff_formula         'c10 h10 n2 o8 s1'
_reflns_odcompleteness_completeness 99.70
_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 Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C18(H18), C19(H19),
 C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;