Sigillins from Springtails Are Potent Natural Insecticides.
Steinbiss, Michael; Maczka, Michael; Langewald, Juergen; London, Brecht; Vallinayagam, Ramakrishnan; Jones, Peter G.; Bastiaans, Harold; Schulz, Stefan; Journal of natural products 83 (2020) 468–472; doi:10.1021/acs.jnatprod.9b01013

data_1557312
_publ_section_title
;
 Sigillins from Springtails Are Potent Natural Insecticides.
;
_journal_issue                   2
_journal_name_full               'Journal of natural products'
_journal_page_first              468
_journal_page_last               472
_journal_paper_doi               10.1021/acs.jnatprod.9b01013
_journal_volume                  83
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C12 H14 Cl6 O5'
_chemical_formula_weight         450.93
_chemical_name_common            'Sigillin F'
_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_Hall           'P 4w'
_space_group_name_H-M_alt        'P 41'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.98338(13)
_cell_length_b                   8.98338(13)
_cell_length_c                   20.8299(7)
_cell_measurement_reflns_used    18473
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.9580
_cell_measurement_theta_min      4.9060
_cell_volume                     1681.00(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-2017
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3543
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Atlas, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            34679
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        75.000
_diffrn_reflns_theta_max         76.276
_diffrn_reflns_theta_min         4.923
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    9.530
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43c (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.782
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1528 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.024(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3471
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0227
_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^)+(0.0263P)^2^+0.1990P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0509
_refine_ls_wR_factor_ref         0.0520
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                3336
_reflns_number_total             3471
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b01013_si_001.cif
_cod_data_source_block           match
_cod_depositor_comments
'Adding full bibliography for 1557311--1557312.cif.'
_cod_original_cell_volume        1680.99(7)
_cod_database_code               1557312
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.329
_shelx_estimated_absorpt_t_max   0.702
_shelx_res_checksum              134
_shelx_hkl_checksum              83132