A nucleophilic addition ring closure [NARC]-based synthesis of (+) -nonactic acid
Fraser, Benjamin; Perlmutter, Patrick; Journal of the Chemical Society, Perkin Transactions 1  (2002) 2896–; doi:10.1039/b206656d

data_7204489
_publ_section_title
;
 A nucleophilic addition ring closure [NARC]-based synthesis of (+)
 -nonactic acid
;
_journal_issue                   24
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2896
_journal_paper_doi               10.1039/b206656d
_journal_year                    2002
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C36 H50 Cl1 Hg1 N1 O5 S1 Si1'
_chemical_formula_structural     'C36 H50 CL1 HG1 N1 O5 S1 SI1'
_chemical_formula_sum            'C36 H50 Cl Hg N O5 S Si'
_chemical_formula_weight         872.96
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5515(1)
_cell_length_b                   19.0540(1)
_cell_length_c                   25.3617(2)
_cell_measurement_reflns_used    38127
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.9
_cell_volume                     3649.20(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.104717
_diffrn_orient_matrix_UB_12      0.323086E-1
_diffrn_orient_matrix_UB_13      0.743408E-1
_diffrn_orient_matrix_UB_21      -0.303809E-1
_diffrn_orient_matrix_UB_22      0
_diffrn_orient_matrix_UB_23      -0.427949E-1
_diffrn_orient_matrix_UB_31      -0.78442E-2
_diffrn_orient_matrix_UB_32      -0.38238E-1
_diffrn_orient_matrix_UB_33      0.55688E-2
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0363
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            38911
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.90
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    4.423
_exptl_absorpt_correction_T_max  0.6885
_exptl_absorpt_correction_T_min  0.4556
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
PLATON Reference : Spek, A.L. (1990), Acta Cryst. A46, 
C-34
a grid of  8 x  8 x  8 =   512 sampling points was used
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.932
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.003(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     422
_refine_ls_number_reflns         8889
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0217
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w=1/[\s^2^(Fo^2^)+(0.0158P)^2^+0.9320P] where 
P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0444
_refine_ls_wR_factor_ref         0.0450
_reflns_number_gt                8488
_reflns_number_total             8889
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b206656d.txt
_cod_data_source_block           bf_m
_cod_original_formula_sum        'C36 H50 Cl1 Hg1 N1 O5 S1 Si1'
_cod_database_code               7204489
_exptl_absorpt_correction_t_ave  0.6342