A switchable dual organocatalytic system and the enantioselective total synthesis of the quadrane sesquiterpene suberosanone
Yajun Ren; Marc Presset; Jeremy Godemert; Nicolas Vanthuyne; Jean-Valere Naubron; Michel Giorgi; Jean Rodriguez; Yoann Coquerel; Chem.Commun. 52 (2016) 6565–; doi:

data_7119103
_publ_section_title
;
 A switchable dual organocatalytic system and the enantioselective total
 synthesis of the quadrane sesquiterpene suberosanone
;
_journal_name_full               Chem.Commun.
_journal_page_first              6565
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H28 O3'
_chemical_formula_sum            'C16 H28 O3'
_chemical_formula_weight         268.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-04-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-01-25 deposited with the CCDC.
2016-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.67202(7)
_cell_length_b                   12.80551(14)
_cell_length_c                   18.3291(2)
_cell_measurement_reflns_used    4478
_cell_measurement_temperature    223.00(10)
_cell_measurement_theta_max      69.3470
_cell_measurement_theta_min      5.9250
_cell_volume                     1566.01(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      223.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
  1 omega -118.00  -72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -35.3416 -128.0000   74.0000 46

  2 omega -124.00  -79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -35.3416  -99.0000   60.0000 45

  3 omega -124.00  -79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -35.3416  -99.0000 -180.0000 45

  4 omega -124.00  -79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -35.3416  -99.0000 -150.0000 45

  5 omega -124.00  -79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -35.3416  -99.0000    0.0000 45

  6 omega   55.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.3416 -178.0000 -120.0000 75

  7 omega   57.00  132.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.3416  178.0000 -180.0000 75

  8 omega   68.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0077   45.0000   60.0000 110

  9 omega   18.00   71.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0077  -30.0000  150.0000 53

 10 omega   42.00   93.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0077  -45.0000   90.0000 51

 11 omega   19.00   53.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0077  -30.0000 -180.0000 34

 12 omega   20.00   96.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0077  -45.0000  -90.0000 76

 13 omega   38.00  143.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0077  -77.0000   90.0000 105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.2001413000
_diffrn_orient_matrix_UB_12      -0.0403201000
_diffrn_orient_matrix_UB_13      -0.0310043000
_diffrn_orient_matrix_UB_21      -0.0842474000
_diffrn_orient_matrix_UB_22      -0.0093128000
_diffrn_orient_matrix_UB_23      0.0779931000
_diffrn_orient_matrix_UB_31      -0.0784981000
_diffrn_orient_matrix_UB_32      0.1129567000
_diffrn_orient_matrix_UB_33      -0.0045546000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5568
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.232
_diffrn_reflns_theta_min         4.212
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1146 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2867
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0632P)^2^+0.1045P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0899
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                2805
_reflns_number_total             2867
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc01689h2.cif
_cod_data_source_block           ryj030193
_cod_original_cell_volume        1566.02(3)
_cod_database_code               7119103
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'c15 h28 o3'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C6(H6A,H6B)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C14(H14A,H14B,
 H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'