Carbonyl anti-(α-Amino)allylation via Ruthenium Catalyzed Hydrogen Autotransfer: Use of an Acetylenic Pyrrole as an Allylmetal Pronucleophile.
Zhang, Wandi; Chen, Weijie; Xiao, Hongde; Krische, Michael J.; Organic letters 19 (2017) 4876–4879; doi:10.1021/acs.orglett.7b02336

data_1547580
_publ_section_title
;
 Carbonyl anti-(\a-Amino)allylation via Ruthenium Catalyzed Hydrogen
 Autotransfer: Use of an Acetylenic Pyrrole as an Allylmetal
 Pronucleophile.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4876
_journal_page_last               4879
_journal_paper_doi               10.1021/acs.orglett.7b02336
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C15 H20 F N O3'
_chemical_formula_sum            'C15 H20 F N O3'
_chemical_formula_weight         281.32
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_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
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_cell_length_c                   26.361(4)
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_cell_measurement_theta_max      69.8
_cell_measurement_theta_min      4.33
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'CrysAlisPro V 1.171.38.43f, Agilent Technologies'
_computing_data_collection
'CrysAlisPro V 1.171.38.43f, Agilent Technologies'
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'CrysAlisPro V 1.171.38.43f, Agilent Technologies'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'Shelxl-2016/6, Sheldrick, G. M.'
_computing_structure_refinement  'Shelxl-2016/6, Sheldrick, G. M.'
_computing_structure_solution
;

SHELXT. Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8. 
;
_diffrn_ambient_temperature      100(2)
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_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device_type  'Agilent SuperNova with Atlas S2 CCD'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0979
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3095
_diffrn_reflns_point_group_measured_fraction_full 0.801
_diffrn_reflns_point_group_measured_fraction_max 0.748
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.126
_diffrn_reflns_theta_min         3.353
_diffrn_source                   'microfocus sealed tube'
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_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.602
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_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details
;
 Flack x determined using 336 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2260
_refine_ls_number_restraints     120
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.1075
_refine_ls_R_factor_gt           0.0859
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0829P)^2^+1.2790P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2060
_refine_ls_wR_factor_ref         0.2259
_reflns_Friedel_coverage         0.346
_reflns_Friedel_fraction_full    0.529
_reflns_Friedel_fraction_max     0.472
_reflns_number_gt                1786
_reflns_number_total             2260
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02336_si_002.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        1462.8(5)
_cod_database_code               1547580
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.783
_shelx_estimated_absorpt_t_max   0.984
_shelx_res_checksum              47684
_shelx_hkl_checksum              79783