Organocatalytic Asymmetric Synthesis of Chiral Dioxazinanes and Dioxazepanes with in Situ Generated Nitrones via a Tandem Reaction Pathway Using a Cooperative Cation Binding Catalyst.
Liu, Yidong; Ao, Jun; Paladhi, Sushovan; Song, Choong Eui; Yan, Hailong; Journal of the American Chemical Society 138 (2016) 16486–16492; doi:10.1021/jacs.6b10660

data_4131198
_publ_section_title
;
 Organocatalytic Asymmetric Synthesis of Chiral Dioxazinanes and
 Dioxazepanes with in Situ Generated Nitrones via a Tandem Reaction
 Pathway Using a Cooperative Cation Binding Catalyst.
;
_journal_issue                   50
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16486
_journal_page_last               16492
_journal_paper_doi               10.1021/jacs.6b10660
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H30 Br N O5'
_chemical_formula_sum            'C22 H30 Br N O5'
_chemical_formula_weight         468.38
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-03-14
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.09.16 svn.r3215 for OlexSys, GUI svn.r5097)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0690(3)
_cell_length_b                   16.0832(8)
_cell_length_c                   23.2308(13)
_cell_measurement_reflns_used    1901
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      21.9850
_cell_measurement_theta_min      3.5840
_cell_volume                     2267.5(2)
_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      293(2)
_diffrn_detector_area_resol_mean 16.0892
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0640
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            7065
_diffrn_reflns_point_group_measured_fraction_full 0.892
_diffrn_reflns_point_group_measured_fraction_max 0.749
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.243
_diffrn_reflns_theta_min         3.470
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.844
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.372
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_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 760 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4622
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0146P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0779
_reflns_Friedel_coverage         0.508
_reflns_Friedel_fraction_full    0.746
_reflns_Friedel_fraction_max     0.588
_reflns_number_gt                2928
_reflns_number_total             4622
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b10660_si_002.cif
_cod_data_source_block           20160314-yanhailong-liuyidong-aj-196
_cod_original_cell_volume        2267.53(19)
_cod_database_code               4131198
_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.a Ternary CH refined with riding coordinates:
 C9(H008), C12(H00E), C11(H00F)
2.b Secondary CH2 refined with riding coordinates:
 C8(H00A,H00C), C13(H00G,H00J), C10(H00K,H00L), C17(H00M,H00N), C16(H00R,H00S),
  C15(H00T,H00U), C14(H00Z,HB)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H00B), C3(H00D), C5(H00H), C6(H00I)
2.d Idealised Me refined as rotating group:
 C21(H00O,H00P,H00Q), C22(H00V,H00W,H00X), C20(H00Y,H,HA)
;
_shelx_res_checksum              14646
_shelx_hkl_checksum              33486
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'