Atroposelective Construction of Axially Chiral Enamides via N‑Allylic Alkylation
Li, Xin; Zhou, Qianyi; Chemical Communications  (2022) –; doi:10.1039/D2CC01000C

data_7129863
_publ_section_title
;
 Atroposelective Construction of Axially Chiral Enamides via
 N&#x2011;Allylic Alkylation
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01000C
_journal_year                    2022
_chemical_formula_moiety         'C31 H31 Br I N O3'
_chemical_formula_sum            'C31 H31 Br I N O3'
_chemical_formula_weight         672.38
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-31 deposited with the CCDC.	2022-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                82.079(4)
_cell_angle_beta                 69.450(5)
_cell_angle_gamma                61.749(6)
_cell_formula_units_Z            4
_cell_length_a                   14.3867(9)
_cell_length_b                   14.4019(8)
_cell_length_c                   16.0728(8)
_cell_measurement_reflns_used    12943
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      31.5460
_cell_measurement_theta_min      1.8400
_cell_volume                     2745.2(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 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      113.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.894
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -115.00  65.00   1.00    2.00    --  -25.00  45.00   0.00  180
  2  \w   -115.00  65.00   1.00    2.00    --  -25.00  45.00  90.00  180
  3  \w   -115.00  65.00   1.00    2.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0283881000
_diffrn_orient_matrix_UB_12      -0.0220449000
_diffrn_orient_matrix_UB_13      -0.0122741000
_diffrn_orient_matrix_UB_21      0.0185892000
_diffrn_orient_matrix_UB_22      0.0139295000
_diffrn_orient_matrix_UB_23      -0.0446470000
_diffrn_orient_matrix_UB_31      0.0485566000
_diffrn_orient_matrix_UB_32      -0.0494936000
_diffrn_orient_matrix_UB_33      -0.0089304000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0847
_diffrn_reflns_av_unetI/netI     0.1339
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            41517
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.938
_diffrn_reflns_theta_min         1.606
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.655
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)'
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.434
_refine_diff_density_min         -1.160
_refine_diff_density_rms         0.169
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     667
_refine_ls_number_reflns         18410
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.0568
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0230P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.1145
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10751
_reflns_number_total             18410
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc01000c2.cif
_cod_data_source_block           r20210720b
_cod_database_code               7129863
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.676
_shelx_estimated_absorpt_t_min   0.593
_reflns_odcompleteness_completeness 99.88
_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
2.a Ternary CH refined with riding coordinates:
 C3(H3), C5(H5), C9(H9), C34(H34), C36(H36), C40(H40)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C10(H10A,
 H10B), C14(H14A,H14B), C22(H22A,H22B), C23(H23A,H23B), C33(H33A,H33B),
 C35(H35A,H35B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B), C41(H41A,H41B),
  C45(H45A,H45B), C53(H53A,H53B), C54(H54A,H54B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C20(H20), C27(H27), C28(H28), C30(H30),
 C31(H31), C48(H48), C49(H49), C50(H50), C51(H51), C58(H58), C59(H59), C61(H61),
  C62(H62)
2.d X=CH2 refined with riding coordinates:
 C13(H13A,H13B), C44(H44A,H44B)
;
_shelx_res_checksum              20001
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.967
_oxdiff_exptl_absorpt_empirical_full_min 0.538