Palladium-Catalyzed Synthesis of 3-Haloindol-2-amines from 3-Diazoindolin-2-imines and Alkyl Halides.
Zhou, Yuxuan; Li, Zhenmin; Ma, Fanghui; Zhao, Chang; Lu, Ping; Wang, Yanguang; The Journal of organic chemistry 84 (2019) 6655–6668; doi:10.1021/acs.joc.9b00191

data_4033600
_publ_section_title
;
 Palladium-Catalyzed Synthesis of 3-Haloindol-2-amines from
 3-Diazoindolin-2-imines and Alkyl Halides.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6655
_journal_page_last               6668
_journal_paper_doi               10.1021/acs.joc.9b00191
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C19 H19 Br N2 O2 S'
_chemical_formula_sum            'C19 H19 Br N2 O2 S'
_chemical_formula_weight         419.33
_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     dual
_audit_creation_date             2018-03-27
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
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_cell_length_b                   9.1695(5)
_cell_length_c                   12.8814(7)
_cell_measurement_reflns_used    3953
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_cell_measurement_theta_max      29.3457
_cell_measurement_theta_min      3.0460
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_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)
;
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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)
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_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_details
;
  1 omega  -85.00  -12.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
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  2 omega  -26.00    1.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
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  3 omega  -74.00   -6.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
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  4 omega  -71.00  -46.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  128.0000 -160.0000 25

  5 omega  -13.00   85.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   38.0000   60.0000 98

  6 omega  -10.00   86.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   38.0000  150.0000 96

  7 omega  -13.00   74.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
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  8 omega  -37.00   45.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
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  9 omega  -15.00   87.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   77.0000  -60.0000 102
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_diffrn_orient_matrix_UB_12      -0.0256330000
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_diffrn_orient_matrix_UB_21      -0.0286419000
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_diffrn_orient_matrix_UB_32      -0.0334941000
_diffrn_orient_matrix_UB_33      -0.0327411000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.998
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_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
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_diffrn_reflns_number            13774
_diffrn_reflns_point_group_measured_fraction_full 0.998
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         3.052
_diffrn_source                   'Enhance (Mo) X-ray Source'
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_exptl_absorpt_correction_T_min  0.85982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
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_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_reflns         3389
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_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0538
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_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0421P)^2^+0.3666P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_number_gt                2682
_reflns_number_total             3389
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00191_si_002.cif
_cod_data_source_block           180327_zyx427010_2
_cod_depositor_comments
'Adding full bibliography for 4033600--4033601.cif.'
_cod_database_code               4033600
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c h o n s br'
_shelx_estimated_absorpt_t_max   0.582
_shelx_estimated_absorpt_t_min   0.522
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_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:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14)
2.c X=CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              64922
_shelx_hkl_checksum              5469
_olex2_submission_special_instructions 'No special instructions were received'