Ligand-Controlled Ni(0)–Al(III) Bimetal-Catalyzed C3–H Alkenylation of 2-Pyridones by Reversing Conventional Selectivity
Yin, Ge; Li, Yue; Wang, Rong-Hua; Li, Jiang-Fei; Xu, Xue-Tao; Luan, Yu-Xin; Ye, Mengchun; ACS Catalysis 11 (2021) 4606–4612; doi:10.1021/acscatal.1c00750

data_4518675
_publ_section_title
;
 Ligand-Controlled Ni(0)--Al(III) Bimetal-Catalyzed C3--H Alkenylation of
 2-Pyridones by Reversing Conventional Selectivity
;
_journal_issue                   8
_journal_name_full               'ACS Catalysis'
_journal_page_first              4606
_journal_page_last               4612
_journal_paper_doi               10.1021/acscatal.1c00750
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C26 H29 N O'
_chemical_formula_sum            'C26 H29 N O'
_chemical_formula_weight         371.50
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-03-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                79.86(3)
_cell_angle_beta                 77.01(3)
_cell_angle_gamma                76.01(3)
_cell_formula_units_Z            8
_cell_length_a                   13.737(3)
_cell_length_b                   14.478(3)
_cell_length_c                   22.319(5)
_cell_measurement_reflns_used    8414
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.8864
_cell_measurement_theta_min      1.5563
_cell_volume                     4162.1(17)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            40308
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.020
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_min         1.556
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.8828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1017
_refine_ls_number_reflns         14669
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0717
_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^)+(0.1104P)^2^+0.2187P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1892
_refine_ls_wR_factor_ref         0.2149
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10292
_reflns_number_total             14669
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c00750_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4518675
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.986
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1(0.043) H2(0.049) H3(0.054) H4(0.056) H5(0.049) H8(0.042)
 H9(0.045) H11(0.041) H12(0.042) H13A(0.048) H13B(0.048) H14(0.05) H15(0.055)
 H16(0.049) H20A(0.054) H20B(0.054) H21A(0.06) H21B(0.06) H22A(0.098)
 H22B(0.098) H22C(0.098) H23(0.054) H24A(0.066) H24B(0.066) H25A(0.071)
 H25B(0.071) H26A(0.1) H26B(0.1) H26C(0.1) H27(0.036) H28(0.039) H29(0.041)
 H30(0.039) H31(0.036) H34(0.034) H35(0.036) H37(0.04) H38(0.039) H39A(0.037)
 H39B(0.037) H40(0.037) H41(0.041) H42(0.04) H46A(0.042) H46B(0.042)
 H47A(0.048) H47B(0.048) H48A(0.091) H48B(0.091) H48C(0.091) H49(0.046)
 H50A(0.057) H50B(0.057) H51A(0.049) H51B(0.049) H52A(0.084) H52B(0.084)
 H52C(0.084) H53(0.035) H54(0.039) H55(0.04) H56(0.041) H57(0.036) H60(0.036)
 H61(0.037) H63(0.036) H64(0.037) H65A(0.038) H65B(0.038) H66(0.037) H67(0.04)
 H68(0.038) H72A(0.043) H72B(0.043) H73A(0.049) H73B(0.049) H74A(0.08)
 H74B(0.08) H74C(0.08) H75(0.046) H76A(0.054) H76B(0.054) H77A(0.051)
 H77B(0.051) H78A(0.077) H78B(0.077) H78C(0.077) H79(0.043) H80(0.05)
 H81(0.049) H82(0.046) H83(0.039) H86(0.038) H87(0.039) H89(0.039) H90(0.037)
 H91A(0.044) H91B(0.044) H92(0.045) H93(0.051) H94(0.049) H98A(0.05) H98B(0.05)
 H99A(0.058) H99B(0.058) H10A(0.088) H10B(0.088) H10C(0.088) H101(0.048)
 H10D(0.057) H10E(0.057) H10F(0.084) H10G(0.084) H10H(0.145) H10I(0.145)
 H10J(0.145)
 Fixed X: H1(0.789018) H2(0.75397) H3(0.885047) H4(1.049465) H5(1.084622)
 H8(0.817004) H9(0.849693) H11(1.145162) H12(1.112378) H13A(1.097052)
 H13B(0.984293) H14(1.120329) H15(1.075349) H16(0.919784) H20A(0.710746)
 H20B(0.800569) H21A(0.831295) H21B(0.922946) H22A(0.892288) H22B(0.909741)
 H22C(0.796538) H23(0.718212) H24A(0.548163) H24B(0.595529) H25A(0.498188)
 H25B(0.590402) H26A(0.699973) H26B(0.612907) H26C(0.602133) H27(0.721047)
 H28(0.67259) H29(0.732325) H30(0.842509) H31(0.890837) H34(0.853434)
 H35(0.893766) H37(0.863825) H38(0.826832) H39A(0.955054) H39B(0.84085)
 H40(1.081939) H41(1.149857) H42(1.049486) H46A(0.75623) H46B(0.782372)
 H47A(0.950967) H47B(0.858986) H48A(0.86181) H48B(0.971274) H48C(0.953359)
 H49(0.892338) H50A(0.750265) H50B(0.853534) H51A(0.707662) H51B(0.807775)
 H52A(0.739132) H52B(0.664944) H52C(0.638219) H53(1.227206) H54(1.178576)
 H55(1.225537) H56(1.324316) H57(1.370705) H60(1.299367) H61(1.336258)
 H63(1.406675) H64(1.364968) H65A(1.448023) H65B(1.334398) H66(1.577104)
 H67(1.649039) H68(1.551414) H72A(1.255285) H72B(1.278802) H73A(1.445062)
 H73B(1.352873) H74A(1.369882) H74B(1.4755) H74C(1.461431) H75(1.395296)
 H76A(1.247736) H76B(1.351374) H77A(1.21468) H77B(1.312505) H78A(1.231959)
 H78B(1.166581) H78C(1.132906) H79(0.579208) H80(0.537796) H81(0.376369)
 H82(0.258526) H83(0.298382) H86(0.620841) H87(0.656242) H89(0.356023)
 H90(0.320482) H91A(0.606706) H91B(0.493688) H92(0.633385) H93(0.590793)
 H94(0.436999) H98A(0.233277) H98B(0.322803) H99A(0.354161) H99B(0.445399)
 H10A(0.41504) H10B(0.442445) H10C(0.326241) H101(0.23071) H10D(0.065737)
 H10E(0.118128) H10F(0.128237) H10G(0.181352) H10H(0.023989) H10I(0.03298)
 H10J(-0.029334)
 Fixed Y: H1(0.660855) H2(0.711092) H3(0.745562) H4(0.725569) H5(0.675217)
 H8(0.68709) H9(0.648794) H11(0.539051) H12(0.573452) H13A(0.54175)
 H13B(0.522428) H14(0.706793) H15(0.85529) H16(0.895756) H20A(0.742932)
 H20B(0.662751) H21A(0.822023) H21B(0.748189) H22A(0.623362) H22B(0.71061)
 H22C(0.694294) H23(0.900317) H24A(0.883475) H24B(0.857981) H25A(1.021816)
 H25B(1.041108) H26A(0.998965) H26B(1.092983) H26C(0.992374) H27(0.996707)
 H28(1.064885) H29(1.199396) H30(1.263839) H31(1.196251) H34(0.908402)
 H35(0.853379) H37(1.125589) H38(1.18115) H39A(0.884572) H39B(0.933418)
 H40(0.988104) H41(1.095881) H42(1.184265) H46A(1.173313) H46B(1.082619)
 H47A(1.042033) H47B(1.028696) H48A(1.175951) H48B(1.104896) H48C(1.189905)
 H49(1.309706) H50A(1.320366) H50B(1.356708) H51A(1.440433) H51B(1.479168)
 H52A(1.519454) H52B(1.575304) H52C(1.483096) H53(0.484562) H54(0.552762)
 H55(0.695353) H56(0.768067) H57(0.701122) H60(0.677072) H61(0.620541)
 H63(0.34876) H64(0.404904) H65A(0.378981) H65B(0.428861) H66(0.478678)
 H67(0.583012) H68(0.673303) H72A(0.672536) H72B(0.581264) H73A(0.53369)
 H73B(0.529793) H74A(0.677134) H74B(0.600159) H74C(0.682003) H75(0.803548)
 H76A(0.820372) H76B(0.855241) H77A(0.936994) H77B(0.97603) H78A(1.016665)
 H78B(1.073604) H78C(0.982574) H79(1.202722) H80(1.259448) H81(1.259189)
 H82(1.197932) H83(1.144099) H86(1.090147) H87(1.049358) H89(1.130531)
 H90(1.172804) H91A(1.033554) H91B(1.01483) H92(1.196137) H93(1.343137)
 H94(1.382312) H98A(1.221523) H98B(1.145407) H99A(1.299265) H99B(1.230494)
 H10A(1.097413) H10B(1.177938) H10C(1.167824) H101(1.389891) H10D(1.392802)
 H10E(1.340008) H10F(1.532717) H10G(1.480028) H10H(1.475905) H10I(1.583702)
 H10J(1.52828)
 Fixed Z: H1(0.563986) H2(0.66158) H3(0.700074) H4(0.640575) H5(0.543551)
 H8(0.461868) H9(0.361805) H11(0.372901) H12(0.474016) H13A(0.278077)
 H13B(0.287089) H14(0.250266) H15(0.195802) H16(0.159248) H20A(0.108688)
 H20B(0.133528) H21A(0.039986) H21B(0.067019) H22A(0.023773) H22B(-0.02962)
 H22C(-0.000883) H23(0.212377) H24A(0.205595) H24B(0.136779) H25A(0.144259)
 H25B(0.169844) H26A(0.077018) H26B(0.066859) H26C(0.051603) H27(0.632361)
 H28(0.724649) H29(0.7328) H30(0.648838) H31(0.556618) H34(0.556629)
 H35(0.460361) H37(0.374895) H38(0.470427) H39A(0.347107) H39B(0.337961)
 H40(0.317206) H41(0.240381) H42(0.167618) H46A(0.108566) H46B(0.159192)
 H47A(0.093781) H47B(0.065359) H48A(0.001244) H48B(-0.011096) H48C(0.029893)
 H49(0.164259) H50A(0.086376) H50B(0.055502) H51A(0.155086) H51B(0.119501)
 H52A(0.02723) H52B(0.0817) H52C(0.063992) H53(0.635708) H54(0.728103)
 H55(0.733225) H56(0.646085) H57(0.553832) H60(0.47121) H61(0.376124)
 H63(0.460676) H64(0.556615) H65A(0.348486) H65B(0.33859) H66(0.318506)
 H67(0.241016) H68(0.168119) H72A(0.109009) H72B(0.159667) H73A(0.095659)
 H73B(0.064016) H74A(0.002084) H74B(-0.00876) H74C(0.034085) H75(0.165939)
 H76A(0.091309) H76B(0.059144) H77A(0.162414) H77B(0.122897) H78A(0.035156)
 H78B(0.091391) H78C(0.077122) H79(0.553404) H80(0.649251) H81(0.711138)
 H82(0.677872) H83(0.581787) H86(0.487382) H87(0.387342) H89(0.380415)
 H90(0.478776) H91A(0.295822) H91B(0.304667) H92(0.263512) H93(0.205896)
 H94(0.167807) H98A(0.120304) H98B(0.148335) H99A(0.050041) H99B(0.08031)
 H10A(0.043502) H10B(-0.012743) H10C(0.011795) H101(0.219582) H10D(0.201073)
 H10E(0.140917) H10F(0.150957) H10G(0.091001) H10H(0.074452) H10I(0.075652)
 H10J(0.134593)
;
_shelx_res_checksum              2435
_shelx_hkl_checksum              92745
_olex2_submission_special_instructions 'No special instructions were received'