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

data_7156051
_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         'C14 H18 O3, H2 O'
_chemical_formula_sum            'C14 H20 O4'
_chemical_formula_weight         252.30
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-11-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-11-14 deposited with the CCDC.
2018-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.344(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.0329(6)
_cell_length_b                   7.9949(3)
_cell_length_c                   11.4441(6)
_cell_measurement_reflns_used    1488
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.2110
_cell_measurement_theta_min      3.5810
_cell_volume                     1364.14(10)
_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    'olex2.solve (Bourhis et al., 2015)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -25.00    1.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  -60.0000 26

  2 omega    6.00   85.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       16.8419   38.0000   30.0000 79

  3 omega  -53.00   45.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       16.8419  -19.0000 -150.0000 98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0077711000
_diffrn_orient_matrix_UB_12      -0.0228783000
_diffrn_orient_matrix_UB_13      0.0577218000
_diffrn_orient_matrix_UB_21      0.0449478000
_diffrn_orient_matrix_UB_22      -0.0282645000
_diffrn_orient_matrix_UB_23      0.0122290000
_diffrn_orient_matrix_UB_31      0.0135046000
_diffrn_orient_matrix_UB_32      0.0808994000
_diffrn_orient_matrix_UB_33      0.0206421000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5658
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.117
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97865
_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    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2778
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0487
_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^)+(0.0532P)^2^+0.2369P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1303
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1929
_reflns_number_total             2778
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02769a2.cif
_cod_data_source_block           171113_s3_fj
_cod_depositor_comments
'Adding full bibliography for 7156049--7156051.cif.'
_cod_original_cell_volume        1364.15(11)
_cod_database_code               7156051
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3s1
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.970
_reflns_odcompleteness_completeness 99.77
_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
2.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'