Oxidative Asymmetric [2 + 3] Annulation of Aldehydes with Azomethine Imines Enabled by N-Heterocyclic Carbene Catalysis.
Yuan, Shiru; Luo, Yuchen; Peng, Jingyi; Miao, Maozhong; Xu, Jianfeng; Ren, Hongjun; Organic letters 19 (2017) 6100–6103; doi:10.1021/acs.orglett.7b02948

data_1548612
_publ_section_title
;
 Oxidative Asymmetric [2 + 3] Annulation of Aldehydes with Azomethine
 Imines Enabled by N-Heterocyclic Carbene Catalysis.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              6100
_journal_page_last               6103
_journal_paper_doi               10.1021/acs.orglett.7b02948
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C19 H17 Br N2 O2'
_chemical_formula_sum            'C19 H17 Br N2 O2'
_chemical_formula_weight         385.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-06-30
_audit_creation_method
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2066(5)
_cell_length_b                   16.3879(14)
_cell_length_c                   16.6057(16)
_cell_measurement_reflns_used    2020
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2310
_cell_measurement_theta_min      3.2757
_cell_volume                     1689.0(3)
_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
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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_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, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -38.00   50.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   38.0000 -150.0000 88

  2 omega  -75.00   10.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -77.0000  -60.0000 85

  3 omega  -87.00   14.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -38.0000   30.0000 101
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0188790000
_diffrn_orient_matrix_UB_12      0.0034591000
_diffrn_orient_matrix_UB_13      0.0419713000
_diffrn_orient_matrix_UB_21      -0.0543166000
_diffrn_orient_matrix_UB_22      -0.0374932000
_diffrn_orient_matrix_UB_23      0.0064443000
_diffrn_orient_matrix_UB_31      0.0987934000
_diffrn_orient_matrix_UB_32      -0.0213483000
_diffrn_orient_matrix_UB_33      -0.0045118000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10506
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.342
_diffrn_reflns_theta_min         3.493
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.447
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81792
_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    1.515
_exptl_crystal_description       needle
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 751 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.020(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3077
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0323P)^2^+0.3016P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0907
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2254
_reflns_number_total             3077
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02948_si_001.cif
_cod_data_source_block           170630_ysr3c
_cod_database_code               1548612
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c h n o br'
_shelx_estimated_absorpt_t_max   0.696
_shelx_estimated_absorpt_t_min   0.380
_reflns_odcompleteness_completeness 99.65
_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:
 C4(H4), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C18(H18),
 C19(H19)
;
_shelx_res_checksum              71641
_shelx_hkl_checksum              8262
_olex2_submission_special_instructions 'No special instructions were received'