The Construction of Chiral Fused Azabicycles Using a Pd-Catalyzed Allylic Substitution Cascade and Asymmetric Desymmetrization Strategy.
An, Qianjin; Liu, Delong; Shen, Jiefeng; Liu, Yangang; Zhang, Wanbin; Organic letters 19 (2017) 238–241; doi:10.1021/acs.orglett.6b03529

data_1544967
_publ_section_title
;
 The Construction of Chiral Fused Azabicycles Using a Pd-Catalyzed Allylic
 Substitution Cascade and Asymmetric Desymmetrization Strategy.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              238
_journal_page_last               241
_journal_paper_doi               10.1021/acs.orglett.6b03529
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C20 H21 N O2 S'
_chemical_formula_sum            'C20 H21 N O2 S'
_chemical_formula_weight         339.44
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-04-25
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Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
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_cell_length_b                   9.4230(4)
_cell_length_c                   28.5737(12)
_cell_measurement_reflns_used    4177
_cell_measurement_temperature    293(2)
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_computing_cell_refinement
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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)
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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)
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_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)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
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_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0388549000
_diffrn_orient_matrix_UB_12      0.0695778000
_diffrn_orient_matrix_UB_13      0.0037941000
_diffrn_orient_matrix_UB_21      0.0841810000
_diffrn_orient_matrix_UB_22      0.0137478000
_diffrn_orient_matrix_UB_23      0.0155592000
_diffrn_orient_matrix_UB_31      0.0612735000
_diffrn_orient_matrix_UB_32      0.0252084000
_diffrn_orient_matrix_UB_33      -0.0189711000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
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_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10289
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.04
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92774
_exptl_absorpt_correction_type   multi-scan
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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)
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    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack (1983), 1292 Friedel pairs'
_refine_ls_abs_structure_Flack   0.00(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0422P)^2^+0.1335P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0864
_reflns_number_gt                2785
_reflns_number_total             3138
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b03529_si_003.cif
_cod_data_source_block           160425_aqj_0422
_cod_depositor_comments
'Adding full bibliography for 1544966--1544967.cif.'
_cod_original_cell_volume        1718.28(12)
_cod_database_code               1544967
_chemical_oxdiff_formula         'C30 H20 N8 O10 S1'
_reflns_odcompleteness_completeness 99.66
_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:
 C7(H7), C8(H8), C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20)
;