Transfer of axial chirality through the nickel-catalysed hydrocyanation of chiral allenes.
Amako, Yuka; Arai, Shigeru; Nishida, Atsushi; Organic & biomolecular chemistry 15 (2017) 1612–1617; doi:10.1039/c7ob00047b

data_7155454
_publ_section_title
;
 Transfer of axial chirality through the nickel-catalysed hydrocyanation
 of chiral allenes.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1612
_journal_page_last               1617
_journal_paper_doi               10.1039/c7ob00047b
_journal_volume                  15
_journal_year                    2017
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C9 H13 N3 O5 S'
_chemical_formula_sum            'C9 H13 N3 O5 S'
_chemical_formula_weight         275.28
_chemical_melting_point          396
_chemical_name_systematic
(E)-3,3-dimethyl-2-((S)-4-((E)-styryl)-1-tosylpyrrolidin-3-ylidene)butanenitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2016-12-06 deposited with the CCDC.
2017-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 104.0503(10)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   12.2397(2)
_cell_length_b                   7.42711(13)
_cell_length_c                   12.5508(2)
_cell_measurement_reflns_used    10110
_cell_measurement_temperature    93
_cell_measurement_theta_max      68.17
_cell_measurement_theta_min      3.63
_cell_volume                     1106.80(3)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2.2'
_computing_publication_material  'CrystalStructure 4.2.2 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXD97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11915
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        68.170
_diffrn_reflns_theta_max         68.170
_diffrn_reflns_theta_min         3.630
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.830
_exptl_absorpt_correction_T_max  0.754
_exptl_absorpt_correction_T_min  0.631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             576.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.32
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1658 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3854
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0228P)^2^+0.3596P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0971
_reflns_number_gt                3246
_reflns_number_total             3854
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c7ob00047b2.cif
_cod_data_source_block           amako161205
_cod_depositor_comments
;
          Adding full bibliography for 7155454.cif.

2018-02-05
Z value changed to be consistent with given formula
                 miguel
;
_cod_original_formula_units_Z            4
_cod_original_cell_volume        1106.81(3)
_cod_database_code               7155454