First Enantioselective Synthesis and Absolute Stereochemistry Assignment of New Monocyclic Sesquiterpenes from Artemisia chamaemelifolia
Jean-Pierre Uttaro; Gérard Audran; Elie Palombo; Honoré Monti; Journal of Organic Chemistry 68 (2003) 5407–5410; doi:10.1021/jo034424y

data_4022462
_publ_section_title
;
 First Enantioselective Synthesis and Absolute Stereochemistry
 Assignment of New Monocyclic Sesquiterpenes from
 Artemisia chamaemelifolia
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5407
_journal_page_last               5410
_journal_paper_doi               10.1021/jo034424y
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C15 H26 O3'
_chemical_formula_weight         254.36
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9850(4)
_cell_length_b                   13.051(1)
_cell_length_c                   16.103(2)
_cell_measurement_reflns_used    1722
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.41
_cell_measurement_theta_min      2.53
_cell_volume                     1468.0(2)
_computing_cell_refinement
'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD (Nonius, 1998)'
_computing_data_reduction
'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Phi scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.05
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1674
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         2.97
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .1
_exptl_crystal_size_min          .1
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       0.67(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1674
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.1128
_refine_ls_R_factor_gt           0.1075
_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^)+(0.1800P)^2^+1.9700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2991
_refine_ls_wR_factor_ref         0.3053
_reflns_number_gt                1564
_reflns_number_total             1674
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo034424ysi20030404_014823.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4022462