Cobalt(iii)-catalyzed cross-coupling of enamides with allyl acetates/maleimides
Yu, Wenlong; Zhang, Wei; Liu, Yue; Liu, Zhanxiang; Zhang, Yuhong; Organic Chemistry Frontiers 4 (2017) 77–; doi:10.1039/C6QO00479B

data_1553543
_publ_section_title
;
 Cobalt(iii)-catalyzed cross-coupling of enamides with allyl
 acetates/maleimides
;
_journal_issue                   1
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              77
_journal_paper_doi               10.1039/C6QO00479B
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C22 H21 N O2'
_chemical_formula_sum            'C22 H21 N O2'
_chemical_formula_weight         331.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-03-14
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2016-07-12 deposited with the CCDC.
2016-10-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.092(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3480(9)
_cell_length_b                   22.781(3)
_cell_length_c                   11.2360(15)
_cell_measurement_reflns_used    1301
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4020
_cell_measurement_theta_min      3.2509
_cell_volume                     1845.7(4)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
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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)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0686832000
_diffrn_orient_matrix_UB_12      0.0222507000
_diffrn_orient_matrix_UB_13      0.0109646000
_diffrn_orient_matrix_UB_21      0.0218805000
_diffrn_orient_matrix_UB_22      -0.0082349000
_diffrn_orient_matrix_UB_23      0.0620407000
_diffrn_orient_matrix_UB_31      0.0668805000
_diffrn_orient_matrix_UB_32      -0.0201551000
_diffrn_orient_matrix_UB_33      -0.0132363000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7149
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.26
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
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
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3366
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1248
_refine_ls_R_factor_gt           0.0677
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1103P)^2^+0.1115P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1801
_refine_ls_wR_factor_ref         0.2255
_reflns_number_gt                1750
_reflns_number_total             3366
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6qo00479b3.cif
_cod_data_source_block           160314_ywl7_073_4_1
_cod_database_code               1553543
_chemical_oxdiff_formula         'C9 H8 O4 n2'
_reflns_odcompleteness_completeness 99.48
_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. Uiso/Uaniso restraints and constraints
O1 \\sim O2 \\sim C15 \\sim C16 \\sim O1A \\sim O2A \\sim C16A: within 1.7A
with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Sof(O1A)=Sof(O2A)=Sof(C16A)=Sof(H16C)=Sof(H16D)=1-FVAR(1)
 Sof(O1)=Sof(O2)=Sof(C16)=Sof(H16A)=Sof(H16B)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C16A(H16C,H16D)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C9(H9), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22)
4.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;