Pd(ii)-Catalyzed aerobic 1,2-difunctionalization of conjugated dienes: efficient synthesis of morpholines and 2-morpholones.
Wen, Ke; Wu, Zhengxing; Chen, Buyun; Chen, Jianzhong; Zhang, Wanbin; Organic & biomolecular chemistry 16 (2018) 5618–5625; doi:10.1039/c8ob01291a

data_7156314
_publ_section_title
;
 Pd(ii)-Catalyzed aerobic 1,2-difunctionalization of conjugated dienes:
 efficient synthesis of morpholines and 2-morpholones.
;
_journal_issue                   31
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5618
_journal_page_last               5625
_journal_paper_doi               10.1039/c8ob01291a
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C18 H25 N O4 S'
_chemical_formula_sum            'C18 H25 N O4 S'
_chemical_formula_weight         351.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-03-06
_audit_creation_method
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
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_audit_update_record
;
2018-03-24 deposited with the CCDC.
2018-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                63.440(8)
_cell_angle_beta                 84.691(6)
_cell_angle_gamma                84.975(7)
_cell_formula_units_Z            2
_cell_length_a                   8.2097(6)
_cell_length_b                   11.3718(10)
_cell_length_c                   11.4320(9)
_cell_measurement_reflns_used    1949
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4119
_cell_measurement_theta_min      3.2754
_cell_volume                     949.27(15)
_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)
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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)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -72.00   15.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -38.0000  -30.0000 87

  2 omega  -38.00   64.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   38.0000  150.0000 102

  3 omega  -22.00   67.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   77.0000  -90.0000 89
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0815863000
_diffrn_orient_matrix_UB_12      0.0153936000
_diffrn_orient_matrix_UB_13      -0.0255422000
_diffrn_orient_matrix_UB_21      -0.0114265000
_diffrn_orient_matrix_UB_22      0.0601251000
_diffrn_orient_matrix_UB_23      0.0051099000
_diffrn_orient_matrix_UB_31      0.0276360000
_diffrn_orient_matrix_UB_32      -0.0320018000
_diffrn_orient_matrix_UB_33      0.0644194000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0813
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6022
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         3.282
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83674
_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    1.230
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.952
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0524
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0265P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.1075
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2133
_reflns_number_total             3462
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01291a2.cif
_cod_data_source_block           180306_leu_noh_cw
_cod_depositor_comments
'Adding full bibliography for 7156313--7156318.cif.'
_cod_database_code               7156314
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H N O S'
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.928
_reflns_odcompleteness_completeness 99.51
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C11A)=Sof(H11D)=Sof(H11E)=Sof(H11F)=1-FVAR(1)
 Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(H11C)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
3.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C16(H16), C17(H17)
3.d X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
3.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C18(H18A,H18B,H18C), C11(H11A,H11B,H11C),
 C11A(H11D,H11E,H11F)
;
_shelx_res_checksum              30084
_olex2_submission_special_instructions 'No special instructions were received'