Asymmetric Allylic C-H Alkylation of Allyl Ethers with 2-Acylimidazoles.
Wang, Tian-Ci; Fan, Lian-Feng; Shen, Yang; Wang, Pu-Sheng; Gong, Liu-Zhu; Journal of the American Chemical Society 141 (2019) 10616–10620; doi:10.1021/jacs.9b05247

data_4127638
_publ_section_title
;
 Asymmetric Allylic C-H Alkylation of Allyl Ethers with 2-Acylimidazoles.
;
_journal_issue                   27
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10616
_journal_page_last               10620
_journal_paper_doi               10.1021/jacs.9b05247
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C22 H21 Cl N2 O2'
_chemical_formula_sum            'C22 H21 Cl N2 O2'
_chemical_formula_weight         380.86
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.039(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.7278(6)
_cell_length_b                   6.6803(4)
_cell_length_c                   14.4312(9)
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      55.04
_cell_measurement_theta_min      3.75
_cell_volume                     988.81(10)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.02
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15323
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.110
_diffrn_reflns_theta_min         3.749
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.209
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1457 before and 0.0906 after correction. The Ratio of minimum to maximum transmission is 0.6823. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       prism
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1402 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.042(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3764
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1407
_refine_ls_wR_factor_ref         0.1465
_reflns_Friedel_coverage         0.826
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                3472
_reflns_number_total             3764
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b05247_si_002.cif
_cod_data_source_block           20181221wtc_0m
_cod_database_code               4127638
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.889
_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. Others
 Fixed Sof: H3A(0.6) H3B(0.4) C4(0.6) H4A(0.6) H4B(0.6) C4A(0.4) H4AA(0.4)
 H4AB(0.4)
3.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C3(H3B), C7(H7), C8(H8), C11(H11), C12(H12), C14(H14), C15(H15),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
3.d X=CH2 refined with riding coordinates:
 C4(H4A,H4B), C4A(H4AA,H4AB)
3.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              31786
_shelx_hkl_checksum              49328
_olex2_submission_special_instructions 'No special instructions were received'