P-stereogenic PNP pincer-Pd catalyzed intramolecular hydroamination of amino-1,3-dienes.
Yang, Zehua; Xia, Chao; Liu, Delong; Liu, Yangang; Sugiya, Masashi; Imamoto, Tsuneo; Zhang, Wanbin; Organic & biomolecular chemistry 13 (2015) 2694–2702; doi:10.1039/c4ob02402h

data_7154267
_publ_section_title
;
 P-stereogenic PNP pincer-Pd catalyzed intramolecular hydroamination of
 amino-1,3-dienes.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2694
_journal_page_last               2702
_journal_paper_doi               10.1039/c4ob02402h
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H29 N O2 S'
_chemical_formula_sum            'C27 H29 N O2 S'
_chemical_formula_weight         431.57
_chemical_melting_point          388.1(8)
_chemical_name_common            5o
_chemical_name_systematic        5o
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-10-16
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2014-10-20 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.686(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.9708(4)
_cell_length_b                   8.8036(3)
_cell_length_c                   11.9111(5)
_cell_measurement_reflns_used    3449
_cell_measurement_temperature    171.4
_cell_measurement_theta_max      67.2062
_cell_measurement_theta_min      3.7865
_cell_volume                     1126.56(8)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      171.4
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0561964000
_diffrn_orient_matrix_UB_12      0.1514827000
_diffrn_orient_matrix_UB_13      -0.0508222000
_diffrn_orient_matrix_UB_21      0.0229270000
_diffrn_orient_matrix_UB_22      0.0696235000
_diffrn_orient_matrix_UB_23      0.1211494000
_diffrn_orient_matrix_UB_31      0.1299501000
_diffrn_orient_matrix_UB_32      0.0530795000
_diffrn_orient_matrix_UB_33      -0.0137215000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7079
_diffrn_reflns_theta_full        67.32
_diffrn_reflns_theta_max         67.32
_diffrn_reflns_theta_min         5.00
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.455
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72949
_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            colorless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane Hexane'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack (1983), 1402 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3414
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0946P)^2^+0.1188P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1417
_reflns_number_gt                3140
_reflns_number_total             3414
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob02402h2.cif
_cod_data_source_block           20141015_140528_2_3rd
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '387.3-388.8' was changed to
'388.1(8)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 7154266--7154267.cif.
;
_cod_original_cell_volume        1126.55(7)
_cod_database_code               7154267
_chemical_oxdiff_formula         'c10 h10 n2 o8 s1'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.d X=CH2 refined with riding coordinates:
 C26(H26A,H26B)
2.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;