Chemoenzymatic total syntheses of the sesquiterpene (–)-patchoulenoneAspects of this work have been reported in preliminary form: M. Banwell and M. McLeod, Chem. Commun., 1998, 1851.
Banwell, Martin G.; Hockless, David C. R.; McLeod, Malcolm D.; New Journal of Chemistry 27 (2003) 50–; doi:10.1039/b206372g

data_7050412
_publ_section_title
;
 Chemoenzymatic total syntheses of the sesquiterpene
 (--)-patchoulenoneAspects of this work have been reported in
 preliminary form: M. Banwell and M. McLeod, Chem. Commun., 1998, 1851.
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              50
_journal_paper_doi               10.1039/b206372g
_journal_volume                  27
_journal_year                    2003
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C22 H30 O2 '
_chemical_formula_sum            'C22 H30 O2'
_chemical_formula_weight         326.48
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_date             2002-07-01
_audit_creation_method           'by teXsan v1.8'
_audit_update_record
;
1999-02-24  dcrh does report
2002-07-01  acwillis does cif
2002-07-02  passes checkcif with warnings:
* Mass attenuation coefficients for absorption from
International Tables for X-ray Crystallography
Vol IV (1974) Table 2.1C.
* crystal small, data weak, so refln/parameter ratio low.
Non-centrosymmetric space group.
* Data can only be collected to 2theta 120 deg on a AFC6R
diffractometer when the evacuated beam tunnel in used.

;
_cell_angle_alpha                90
_cell_angle_beta                 112.073(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.017(1)
_cell_length_b                   9.245(2)
_cell_length_c                   11.062(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      16.2
_cell_volume                     949.3(2)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan (MSC, 1992-1997)'
_computing_publication_material  'teXsan (MSC, 1992-1997)'
_computing_structure_refinement  'teXsan (MSC, 1992-1997)'
_computing_structure_solution
;
SIR92 (Altomare, et. al. 1994)
;
_diffrn_ambient_temperature      296.2
_diffrn_measured_fraction_theta_max 1.
_diffrn_measurement_device_details
;
Rigaku AFC6R diffractometer with extended arm and
evacuated collimator and beam tunnel.
Data cannot be collected beyond \y 60 deg in this configuration.
;
_diffrn_measurement_device_type  'Rigaku AFC6R'
_diffrn_measurement_method       \w-2\q
_diffrn_orient_matrix_UB_11      -0.10369
_diffrn_orient_matrix_UB_12      -0.00979
_diffrn_orient_matrix_UB_13      -0.01218
_diffrn_orient_matrix_UB_21      0.02441
_diffrn_orient_matrix_UB_22      0.02693
_diffrn_orient_matrix_UB_23      0.09343
_diffrn_orient_matrix_UB_31      -0.01603
_diffrn_orient_matrix_UB_32      0.10431
_diffrn_orient_matrix_UB_33      -0.02526
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.03340
_diffrn_reflns_av_sigmaI/netI    0.100
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            1621
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         60.02
_diffrn_reflns_theta_min         4.32
_diffrn_standards_decay_%        -0.39
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.518
_exptl_absorpt_correction_T_max  .969
_exptl_absorpt_correction_T_min  .907
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
\y scans (North,Phillips & Matthews, 1968)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             356.00
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.13
_refine_diff_density_min         -0.11
_refine_ls_extinction_coef       0.0000034(6)
_refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.'
_refine_ls_extinction_method     'Zachariasen (1967)'
_refine_ls_goodness_of_fit_all   1.511
_refine_ls_goodness_of_fit_ref   1.790
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     217
_refine_ls_number_reflns         864
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(Fo) + 0.00001|Fo|^2^]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.0394
_refine_ls_wR_factor_ref         0.0329
_reflns_number_gt                864
_reflns_number_total             1520
_reflns_threshold_expression     I>3.00\s(I)
_cod_data_source_file            b206372g.txt
_cod_data_source_block           MGB49
_cod_original_sg_symbol_H-M      'P 21       '
_cod_original_formula_sum        'C22 H30 O2 '
_cod_database_code               7050412