Total synthesis of five natural eremophilane-type sesquiterpenoids.
Meng, Zhe; Liu, Bo; Organic & biomolecular chemistry 16 (2018) 957–962; doi:10.1039/c7ob02769a

data_7156049
_publ_section_title
;
 Total synthesis of five natural eremophilane-type sesquiterpenoids.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              957
_journal_page_last               962
_journal_paper_doi               10.1039/c7ob02769a
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C12 H16 O2'
_chemical_formula_sum            'C12 H16 O2'
_chemical_formula_weight         192.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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
_audit_creation_date             2017-04-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-10-06 deposited with the CCDC.
2018-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.212(4)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   15.4159(7)
_cell_length_b                   16.6808(9)
_cell_length_c                   17.3970(6)
_cell_measurement_reflns_used    5127
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.9120
_cell_measurement_theta_min      3.4400
_cell_volume                     4295.7(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, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -22.00   21.20   0.9000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000 -150.0000 48

  2 omega   20.00   51.50   0.9000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   57.0000   60.0000 35

  3 omega  -15.00   21.00   0.9000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000   30.0000 40

  4 omega  -72.00    1.80   0.9000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -38.0000 -120.0000 82

  5 omega  -55.00  -11.80   0.9000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -19.0000  120.0000 48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0141623000
_diffrn_orient_matrix_UB_12      -0.0377037000
_diffrn_orient_matrix_UB_13      -0.0110355000
_diffrn_orient_matrix_UB_21      0.0432894000
_diffrn_orient_matrix_UB_22      0.0161763000
_diffrn_orient_matrix_UB_23      0.0027352000
_diffrn_orient_matrix_UB_31      0.0147751000
_diffrn_orient_matrix_UB_32      -0.0111857000
_diffrn_orient_matrix_UB_33      0.0409293000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20240
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.946
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91822
_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_density_diffrn    1.189
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         8766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0615P)^2^+0.1041P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1397
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5293
_reflns_number_total             8766
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02769a2.cif
_cod_data_source_block           170407_s1_mz
_cod_depositor_comments
'Adding full bibliography for 7156049--7156051.cif.'
_cod_original_cell_volume        4295.8(3)
_cod_database_code               7156049
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.977
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C5A(H5A), C5B(H5B), C5C(H5C), C5D(H5D)
2.b Secondary CH2 refined with riding coordinates:
 C6A(H6AA,H6AB), C7A(H7AA,H7AB), C8A(H8AA,H8AB), C6B(H6BA,H6BB), C7B(H7BA,
 H7BB), C8B(H8BA,H8BB), C6C(H6CA,H6CB), C7C(H7CA,H7CB), C8C(H8CA,H8CB),
 C6D(H6DA,H6DB), C7D(H7DA,H7DB), C8D(H8DA,H8DB)
2.c Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C10A(H10A), C3B(H3B), C10B(H10B), C3C(H3C), C10C(H10C), C3D(H3D),
 C10D(H10D)
2.d Idealised Me refined as rotating group:
 C11A(H11A,H11B,H11C), C12A(H12A,H12B,H12C), C11B(H11D,H11E,H11F), C12B(H12D,
 H12E,H12F), C11C(H11G,H11H,H11I), C12C(H12G,H12H,H12I), C11D(H11J,H11K,H11L),
 C12D(H12J,H12K,H12L)
2.e Idealised tetrahedral OH refined as rotating group:
 O2A(H2A), O2B(H2B), O2C(H2C), O2D(H2D)
;
_olex2_submission_special_instructions 'No special instructions were received'