Regio- and stereoselective synthesis of 2-amino-dienes via decarboxylative amination of 4-(ethoxycarbonyl)-2,3-allenols by TsNCO.
Wu, Lijun; Huang, Hui; Liang, Yun; Cheng, Pi; The Journal of organic chemistry 79 (2014) 11264–11269; doi:10.1021/jo502098b

data_4030122
_publ_section_title
;
 Regio- and stereoselective synthesis of 2-amino-dienes via
 decarboxylative amination of 4-(ethoxycarbonyl)-2,3-allenols by TsNCO.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11264
_journal_page_last               11269
_journal_paper_doi               10.1021/jo502098b
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C21 H22 Br N O5 S'
_chemical_formula_sum            'C21 H22 Br N O5 S'
_chemical_formula_weight         480.36
_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'
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Olex2 1.2
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_cell_measurement_reflns_used    4707
_cell_measurement_temperature    100.00(10)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
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CrysAlisPro, Agilent Technologies,
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_diffrn_orient_matrix_UB_12      0.0338658000
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_diffrn_orient_matrix_UB_32      0.0584287000
_diffrn_orient_matrix_UB_33      0.0030848000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.440
_diffrn_reflns_theta_min         2.903
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
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_refine_ls_number_reflns         5538
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0594
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+1.1170P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_number_total             5538
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo502098b_si_002.cif
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_cod_depositor_comments          'Adding full bibliography for 4030122.cif.'
_cod_original_cell_volume        2086.84(16)
_cod_database_code               4030122
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C3 H8 N O S Br'
_shelx_estimated_absorpt_t_max   0.743
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_reflns_odcompleteness_completeness 99.82
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_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:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C11(H11), C16(H16), C17(H17),
 C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C14(H14A,H14B,H14C), C21(H21A,H21B,H21C)
;