Total Synthesis of (\±)-Isostemofoline
Andrew S. Kende; Terrence L. Smalley; He Huang; Journal of the American Chemical Society 121 (1999) 7431–7432; doi:10.1021/ja991528a

data_4116494
_publ_section_title
;
 Total Synthesis of (\+-)-Isostemofoline
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_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7431
_journal_page_last               7432
_journal_paper_doi               10.1021/ja991528a
_journal_volume                  121
_journal_year                    1999
_chemical_formula_sum            'C16 H23 N O3'
_chemical_formula_weight         277.35
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 105.213(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5560(7)
_cell_length_b                   12.2250(7)
_cell_length_c                   11.7344(8)
_cell_measurement_temperature    193(2)
_cell_volume                     1461.22(16)
_computing_cell_refinement       'Siemens SAINT'
_computing_data_collection       'Siemens SMART'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL-4.05'
_computing_publication_material  'Siemens SHELXTL-4.05'
_computing_structure_refinement  SHELXTL-4.05(Sheldrick)
_computing_structure_solution    'SHELXS-86 (Sheldrick)'
_diffrn_ambient_temperature      193(2)
_diffrn_measurement_device       'SMART CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5780
_diffrn_reflns_theta_max         23.28
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.800989
_exptl_absorpt_correction_T_min  0.573461
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    NA
_exptl_crystal_description       Plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.152
_refine_ls_goodness_of_fit_obs   1.211
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.152
_refine_ls_restrained_S_obs      1.211
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_obs          0.0603
_refine_ls_shift/esd_max         -0.004
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.3797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1289
_refine_ls_wR_factor_obs         0.1179
_reflns_number_observed          1581
_reflns_number_total             2039
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja991528a.cif
_cod_data_source_block           24
_cod_depositor_comments
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The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'NA' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.3797P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.3797P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1461.2(2)
_cod_database_code               4116494