Chemoselective phosphine-catalyzed cyanoacylation of α-dicarbonyl compounds: a general method for the synthesis of cyanohydrin esters with one quaternary stereocenter
Zhang, Honghui; Liu, Rongfang; Liu, Jialin; Fan, Binbin; Li, Ruifeng; Qiao, Yan; Zhou, Rong; New Journal of Chemistry 42 (2018) 19720–; doi:10.1039/C8NJ04867C

data_7057878
_publ_section_title
;
 Chemoselective phosphine-catalyzed cyanoacylation of \a-dicarbonyl
 compounds: a general method for the synthesis of cyanohydrin esters with
 one quaternary stereocenter
;
_journal_issue                   24
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              19720
_journal_paper_doi               10.1039/C8NJ04867C
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C17 H11 Cl N2 O3'
_chemical_formula_sum            'C17 H11 Cl N2 O3'
_chemical_formula_weight         326.73
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2018-05-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2018-07-25 deposited with the CCDC.
2018-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                99.73(3)
_cell_angle_beta                 96.54(3)
_cell_angle_gamma                97.78(3)
_cell_formula_units_Z            2
_cell_length_a                   8.0653(16)
_cell_length_b                   8.4613(17)
_cell_length_c                   12.124(2)
_cell_measurement_reflns_used    2398
_cell_measurement_temperature    113
_cell_measurement_theta_max      28.0470
_cell_measurement_theta_min      2.4733
_cell_volume                     800.0(3)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      113
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Saturn 70'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9464
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.845
_diffrn_reflns_theta_min         2.473
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       prism
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.079(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3763
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0635P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1140
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2581
_reflns_number_total             3763
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj04867c2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments          'Adding full bibliography for 7057878.cif.'
_cod_database_code               7057878
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.937
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              6929
_shelx_hkl_checksum              51296
_olex2_submission_special_instructions 'No special instructions were received'