Palladium-catalyzed asymmetric allylic amination of racemic butadiene monoxide with isatin derivatives.
Li, Gen; Feng, Xiangqing; Du, Haifeng; Organic & biomolecular chemistry 13 (2015) 5826–5830; doi:10.1039/c5ob00663e

data_7154471
_publ_section_title
;
 Palladium-catalyzed asymmetric allylic amination of racemic butadiene
 monoxide with isatin derivatives.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5826
_journal_page_last               5830
_journal_paper_doi               10.1039/c5ob00663e
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H10 Cl N3 O2'
_chemical_formula_sum            'C15 H10 Cl N3 O2'
_chemical_formula_weight         299.71
_chemical_melting_point          426.0(10)
_chemical_name_systematic        mx3217
_chemical_properties_physical    Heat-sensitive
_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
_audit_creation_date             2014-07-23
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_audit_update_record
;
2014-12-05 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.052(2)
_cell_length_b                   19.594(7)
_cell_length_c                   19.706(7)
_cell_measurement_reflns_used    9197
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4851
_cell_measurement_theta_min      1.0333
_cell_volume                     2722.9(16)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution
;
'SHELXS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0347
_diffrn_orient_matrix_UB_12      -0.0437
_diffrn_orient_matrix_UB_13      0.1304
_diffrn_orient_matrix_UB_21      -0.0204
_diffrn_orient_matrix_UB_22      0.0457
_diffrn_orient_matrix_UB_23      0.0099
_diffrn_orient_matrix_UB_31      -0.0448
_diffrn_orient_matrix_UB_32      -0.0162
_diffrn_orient_matrix_UB_33      -0.0174
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0809
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11312
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.508
_diffrn_reflns_theta_min         1.466
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_description       plate
_exptl_crystal_F_000             1232
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 1517 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.14(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         6049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0766
_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^)+(0.0232P)^2^+2.5638P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1400
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.945
_reflns_number_gt                5081
_reflns_number_total             6049
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00663e2.cif
_cod_data_source_block           mx3217a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '425-427' was changed to '426.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7154471.cif.
;
_cod_original_cell_volume        2722.7(17)
_cod_database_code               7154471
_shelxl_version_number           2013-4
_diffrn_number_total             3525
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C9A(H9A)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C12A(H12C,H12D)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C4(H4), C5(H5), C10(H10), C2A(H2AB), C4A(H4A), C5A(H5A), C10A(H10A)
2.d X=CH2 refined with riding coordinates:
 C11(H11A,H11B), C11A(H11C,H11D)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O2A(H2AA)
;
_shelx_res_checksum              17229