Isolation of Picrotoxanes from <i>Austrobuxus carunculatus</i> Using Taxonomy-Based Molecular Networking.
Olivon, Florent; Retailleau, Pascal; Desrat, Sandy; Touboul, David; Roussi, Fanny; Apel, Cécile; Litaudon, Marc; Journal of natural products 83 (2020) 3069–3079; doi:10.1021/acs.jnatprod.0c00636

data_1559266
_publ_section_title
;
 Isolation of Picrotoxanes from <i>Austrobuxus carunculatus</i> Using
 Taxonomy-Based Molecular Networking.
;
_journal_issue                   10
_journal_name_full               'Journal of natural products'
_journal_page_first              3069
_journal_page_last               3079
_journal_paper_doi               10.1021/acs.jnatprod.0c00636
_journal_volume                  83
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H28 O9'
_chemical_formula_sum            'C20 H28 O9'
_chemical_formula_weight         412.42
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.93810(10)
_cell_length_b                   12.3500(3)
_cell_length_c                   23.4283(16)
_cell_measurement_reflns_used    8322
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.6
_cell_volume                     2007.47(15)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Rigaku Rapid2 curved large area IP'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
scan:
	Number of images: 18
	           Slice: 20.0000 - 200.0000
	     Image width: 10.0000
	        Exp time: 1200.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 27.0000
	             Phi: 270.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 18
	           Slice: 20.0000 - 200.0000
	     Image width: 10.0000
	        Exp time: 1200.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 18
	           Slice: 20.0000 - 200.0000
	     Image width: 10.0000
	        Exp time: 1200.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 27.0000
	             Phi: 180.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 15
	           Slice: 20.0000 - 170.0000
	     Image width: 10.0000
	        Exp time: 1200.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 270.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 6
	           Slice: 54.0000 - 123.0000
	     Image width: 10.0000
	        Exp time: 1200.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 27.0000
	             Phi: 90.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 6
	           Slice: 20.0000 - 80.0000
	     Image width: 10.0000
	        Exp time: 1200.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 180.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 4
	           Slice: 65.0000 - 110.0000
	     Image width: 10.0000
	        Exp time: 1200.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 27.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 4
	           Slice: 20.0000 - 60.0000
	     Image width: 10.0000
	        Exp time: 1200.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: 0.0000

;
_diffrn_measurement_device
;
Crystal Goniometer chi-partial
;
_diffrn_measurement_device_type
;
Rigaku MM007HF Spider
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       FS_PROCESS
_diffrn_orient_matrix_UB_11      -0.057561
_diffrn_orient_matrix_UB_12      -0.021663
_diffrn_orient_matrix_UB_13      0.041046
_diffrn_orient_matrix_UB_21      0.049509
_diffrn_orient_matrix_UB_22      0.067385
_diffrn_orient_matrix_UB_23      0.022476
_diffrn_orient_matrix_UB_31      -0.095708
_diffrn_orient_matrix_UB_32      0.047886
_diffrn_orient_matrix_UB_33      -0.013059
_diffrn_radiation_monochromator  'OSMIC CMF optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            24730
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.226
_diffrn_reflns_theta_min         3.773
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.907
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Reqab, (Rigaku-Higashi, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       Tab
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1190 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         3658
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0324
_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^)+(0.0431P)^2^+0.2868P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0878
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                3196
_reflns_number_total             3658
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00636_si_007.cif
_cod_data_source_block           compound-12
_cod_depositor_comments
'Adding full bibliography for 1559261--1559267.cif.'
_cod_database_code               1559266
_shelx_res_checksum              66947
_shelx_hkl_checksum              30706