Nickel-Catalyzed Addition-Type Alkenylation of Unactivated, Aliphatic C-H Bonds with Alkynes: A Concise Route to Polysubstituted γ-Butyrolactones.
Li, Mingliang; Yang, Yudong; Zhou, Danni; Wan, Danyang; You, Jingsong; Organic letters 17 (2015) 2546–2549; doi:10.1021/acs.orglett.5b01128

data_1520757
_publ_section_title
;
 Nickel-Catalyzed Addition-Type Alkenylation of Unactivated, Aliphatic C-H
 Bonds with Alkynes: A Concise Route to Polysubstituted \g-Butyrolactones.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2546
_journal_page_last               2549
_journal_paper_doi               10.1021/acs.orglett.5b01128
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C24 H20 O3'
_chemical_formula_sum            'C24 H20 O3'
_chemical_formula_weight         356.40
_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'
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Olex2 1.2
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_cell_measurement_reflns_used    6764
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
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_diffrn_ambient_temperature      293(2)
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_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_12      -0.0458830000
_diffrn_orient_matrix_UB_13      0.0229291000
_diffrn_orient_matrix_UB_21      -0.0282808000
_diffrn_orient_matrix_UB_22      -0.1346504000
_diffrn_orient_matrix_UB_23      -0.0802365000
_diffrn_orient_matrix_UB_31      0.0022146000
_diffrn_orient_matrix_UB_32      0.1027947000
_diffrn_orient_matrix_UB_33      -0.0947162000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.987
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_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17279
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         25.093
_diffrn_reflns_theta_min         2.622
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38234
_exptl_absorpt_correction_type   multi-scan
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
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_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
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_refine_ls_extinction_method     none
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_refine_ls_number_parameters     245
_refine_ls_number_reflns         3387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0571
_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^)+(0.1160P)^2^+0.1710P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.1641
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_reflns_number_gt                2960
_reflns_number_total             3387
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01128_si_002.cif
_cod_data_source_block           limimgliang
_cod_original_cell_volume        1899.61(17)
_cod_database_code               1520757
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_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
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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:
 C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C9(H9), C20(H20), C19(H19), C21(H21), C11(H11), C10(H10), C5(H5),
 C6(H6), C1(H1), C7(H7), C8(H8), C2(H2), C3(H3), C16(H16)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
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