Synthesis of piperitone-derived halogenated lactones and their effect on aphid probing, feeding, and settling behavior
Grudniewska, Aleksandra; Dancewicz, Katarzyna; Białońska, Agata; Ciunik, Zbigniew; Gabryś, Beata; Wawrzeńczyk, Czesław; RSC Advances 1 (2011) 498–; doi:10.1039/c1ra00270h

data_7238413
_publ_section_title
;
 Synthesis of piperitone-derived halogenated lactones and their effect on
 aphid probing, feeding, and settling behavior
;
_journal_issue                   3
_journal_name_full               'RSC Advances'
_journal_page_first              498
_journal_paper_doi               10.1039/c1ra00270h
_journal_volume                  1
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H19 Br O2'
_chemical_formula_sum            'C12 H19 Br O2'
_chemical_formula_weight         275.18
_chemical_name_systematic
;
(+)-(1<i>S</i>,4<i>R</i>,5<i>R</i>,6<i>R</i>)-5-bromo-4-isopropyl
-1-methyl-7-oxabicyclo[4.3.0]nonan-8-one
;
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.951(2)
_cell_length_b                   8.165(2)
_cell_length_c                   19.191(3)
_cell_measurement_reflns_used    8317
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.73
_cell_measurement_theta_min      2.77
_cell_volume                     1245.9(5)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_structure_refinement
;
SHELXL-97 (Sheldrick, G. M. (2008). <i>Acta Cryst.</i> <b>A64</b>, 112-122.)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, G. M. (2008). <i>Acta Cryst.</i> <b>A64</b>, 112-122.)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Kuma KM4CCD'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10539
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.77
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.280
_exptl_absorpt_correction_T_max  0.789
_exptl_absorpt_correction_T_min  0.368
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.008(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2721
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0239
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0356P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0565
_refine_ls_wR_factor_ref         0.0573
_reflns_number_gt                2518
_reflns_number_total             2721
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ra00270h.txt
_cod_data_source_block           (+)-5a
_cod_database_code               7238413