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_1548767
_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 H24 O2'
_chemical_formula_sum            'C15 H24 O2'
_chemical_formula_weight         236.34
_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
_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                   5.18407(15)
_cell_length_b                   8.7085(3)
_cell_length_c                   29.2276(8)
_cell_measurement_reflns_used    1500
_cell_measurement_temperature    130.01(10)
_cell_measurement_theta_max      75.2600
_cell_measurement_theta_min      5.2870
_cell_volume                     1319.49(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      130.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -49.00  35.00   1.00    2.50    --  -40.81  38.00  30.00   84
  2  \w    -96.00  -2.00   1.00    2.50    --  -40.81 125.00  90.00   94
  3  \w   -115.00 -13.00   1.00    2.50    --  -40.81 -57.00-120.00  102
  4  \w     38.00 107.00   1.00    5.00    --  110.21 -94.00 -60.00   69
  5  \w     60.00 109.00   1.00    5.00    --  110.21 -94.00  30.00   49
  6  \w     39.00  93.00   1.00    5.00    --  110.21 -45.00 -90.00   54
  7  \w     62.00 137.00   1.00    5.00    --  110.21  15.00-120.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0435809000
_diffrn_orient_matrix_UB_12      -0.1746580000
_diffrn_orient_matrix_UB_13      -0.0027944000
_diffrn_orient_matrix_UB_21      -0.2444630000
_diffrn_orient_matrix_UB_22      -0.0267882000
_diffrn_orient_matrix_UB_23      0.0289694000
_diffrn_orient_matrix_UB_31      -0.1635626000
_diffrn_orient_matrix_UB_32      -0.0067266000
_diffrn_orient_matrix_UB_33      -0.0439568000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            7685
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.778
_diffrn_reflns_theta_min         5.300
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description       rod
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 951 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0350
_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^+0.1122P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0858
_reflns_Friedel_coverage         0.664
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                2466
_reflns_number_total             2686
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00616_si_003.cif
_cod_data_source_block           compound_14
_cod_original_cell_volume        1319.50(7)
_cod_database_code               1548767
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C13 H20 O2 F1'
_chemical_oxdiff_usercomment     'Needle in oil at 130 K'
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.832
_reflns_odcompleteness_completeness 93.06
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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:
 C1(H1), C4(H4), C5(H5), C6(H6), C10(H10), C12(H12), C14(H14A)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C9(H9A,H9B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              60095
_shelx_hkl_checksum              18912
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.429
_oxdiff_exptl_absorpt_empirical_full_min 0.685