Enantiospecific first total synthesis and assignment of absolute configuration of the sesquiterpene (-)-cucumin H.
Srikrishna, A.; Dethe, Dattatraya H.; Organic letters 5 (2003) 2295–2298; doi:10.1021/ol034635p

data_1507326
_publ_section_title
;
 Enantiospecific first total synthesis and assignment of absolute
 configuration of the sesquiterpene (-)-cucumin H.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              2295
_journal_page_last               2298
_journal_paper_doi               10.1021/ol034635p
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C22 H25 N O5'
_chemical_formula_weight         383.45
_chemical_name_systematic
;
3-oxo-1,4,4,8-tetramethyltricyclo[6.3.0.0(2,6)]undec-2(6)-en-7-yl
4-nitrobenzoate
;
_space_group_IT_number           4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2002-12-04T17:03:27-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 117.887(5)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   17.450(5)
_cell_length_b                   11.560(3)
_cell_length_c                   17.583(5)
_cell_measurement_temperature    293(2)
_cell_volume                     3135.0(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.1039
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17522
_diffrn_reflns_theta_full        21.97
_diffrn_reflns_theta_max         21.97
_diffrn_reflns_theta_min         1.32
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1236
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.03
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881''
_refine_ls_abs_structure_Flack   1.8(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.878
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     769
_refine_ls_number_reflns         7649
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.878
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0524
_refine_ls_shift/su_max          0.049
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0467P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3''
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1228
_reflns_number_gt                4912
_reflns_number_total             7649
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol034635psi20030422_024142.cif
_cod_data_source_block           dd1_m
_cod_original_cell_volume        3134.8(16)
_cod_database_code               1507326