Asymmetric Homoenolate Additions to Acyl Phosphonates through Rational Design of a Tailored N-Heterocyclic Carbene Catalyst.
Jang, Ki Po; Hutson, Gerri E.; Johnston, Ryne C.; McCusker, Elizabeth O.; Cheong, Paul H.-Y.; Scheidt, Karl A.; Journal of the American Chemical Society 136 (2014) 76–79; doi:10.1021/ja410932t

data_4120679
_publ_section_title
;
 Asymmetric Homoenolate Additions to Acyl Phosphonates through Rational
 Design of a Tailored N-Heterocyclic Carbene Catalyst.
;
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              76
_journal_page_last               79
_journal_paper_doi               10.1021/ja410932t
_journal_volume                  136
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H21 O6 P'
_chemical_formula_sum            'C18 H21 O6 P'
_chemical_formula_weight         364.32
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-10-31
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                69.5090(10)
_cell_angle_beta                 84.3470(10)
_cell_angle_gamma                75.7150(10)
_cell_formula_units_Z            1
_cell_length_a                   7.1747(2)
_cell_length_b                   7.9625(3)
_cell_length_c                   8.5502(3)
_cell_measurement_reflns_used    7377
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.48
_cell_measurement_theta_min      5.52
_cell_volume                     443.37(3)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      99.99
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7706
_diffrn_reflns_theta_full        64.82
_diffrn_reflns_theta_max         64.82
_diffrn_reflns_theta_min         5.52
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.655
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0539 before and 0.0272 after correction.
The Ratio of minimum to maximum transmission is 0.8538.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             192
_exptl_crystal_size_max          0.375
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.002(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2748
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0283
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0577P)^2^+0.0768P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0759
_reflns_number_gt                2743
_reflns_number_total             2748
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja410932t_si_001.cif
_cod_data_source_block           cu_n2667_0m
_cod_database_code               4120679
_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:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C4(H4A,H4B,H4C)
;