Revision of the Phytochemistry of Eremophila sturtii and E. mitchellii
Sadgrove, Nicholas J.; Klepp, Julian; Legendre, Sarah V.A.-M.; Lyddiard, Dane; Sumby, Christopher J.; Greatrex, Ben W.; Journal of Natural Products  (2018) –; doi:10.1021/acs.jnatprod.7b00616

data_1548768
_publ_section_title
;
 Revision of the Phytochemistry of Eremophila sturtii and E. mitchellii
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.7b00616
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H26 O2'
_chemical_formula_sum            'C15 H26 O2'
_chemical_formula_weight         238.36
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-11-02
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8987(3)
_cell_length_b                   11.4701(7)
_cell_length_c                   15.1331(7)
_cell_measurement_reflns_used    4925
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      22.9060
_cell_measurement_theta_min      3.7150
_cell_volume                     1371.04(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_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_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1695
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_details
;
  1 omega  -52.00   38.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6743  -57.0000 -150.0000 90

  2 omega  -90.00   56.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.2993    0.0000   30.0000 146

  3 omega  -25.00   59.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6743  -99.0000  -30.0000 84

  4 omega   -5.00   85.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6743   57.0000    0.0000 90

  5 omega   32.00   93.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6743 -178.0000 -120.0000 61

  6 omega  -25.00   25.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.2993  -99.0000 -150.0000 50

  7 omega  -25.00   25.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.2993  -99.0000   30.0000 50

  8 omega  -41.00   54.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.2993   43.0000   87.0000 95

  9 omega   -5.00   85.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6743   57.0000  -90.0000 90

 10 omega  -25.00   20.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6743  -99.0000  150.0000 45

 11 omega  -25.00   25.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.2993  -99.0000  120.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0384798000
_diffrn_orient_matrix_UB_12      0.0452082000
_diffrn_orient_matrix_UB_13      -0.0248962000
_diffrn_orient_matrix_UB_21      -0.0737298000
_diffrn_orient_matrix_UB_22      -0.0345767000
_diffrn_orient_matrix_UB_23      -0.0049594000
_diffrn_orient_matrix_UB_31      -0.0338837000
_diffrn_orient_matrix_UB_32      0.0241303000
_diffrn_orient_matrix_UB_33      0.0394164000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22156
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        27.000
_diffrn_reflns_theta_max         28.441
_diffrn_reflns_theta_min         3.409
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 797 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3142
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0571
_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^)+(0.0418P)^2^+0.4409P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1303
_reflns_Friedel_coverage         0.685
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.865
_reflns_number_gt                2338
_reflns_number_total             3142
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00616_si_002.cif
_cod_data_source_block           cedranediol_12
_cod_database_code               1548768
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         C15H32O2
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.960
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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:
 C2(H2), C5(H5), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C14(H14A,H14B)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              22554
_shelx_hkl_checksum              86206
_olex2_submission_special_instructions 'No special instructions were received'