Solar irradiation of the seed germination stimulant karrikinolide produces two novel head-to-head cage dimers
Scaffidi, Adrian; Waters, Mark T.; Skelton, Brian W.; Bond, Charles S.; Sobolev, Alexandre N.; Bythell-Douglas, Rohan; McKinley, Allan J.; Dixon, Kingsley W.; Ghisalberti, Emilio L.; Smith, Steven M.; Flematti, Gavin R.; Organic & Biomolecular Chemistry 10 (2012) 4069–; doi:10.1039/c2ob25090j

data_7152320
_publ_section_title
;
 Solar irradiation of the seed germination stimulant karrikinolide
 produces two novel head-to-head cage dimers
;
_journal_issue                   20
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              4069
_journal_paper_doi               10.1039/c2ob25090j
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C16 H12 O6'
_chemical_formula_sum            'C16 H12 O6'
_chemical_formula_weight         300.26
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.0
_cell_angle_beta                 113.283(4)
_cell_angle_gamma                90.0
_cell_formula_units_Z            8
_cell_length_a                   17.0210(5)
_cell_length_b                   11.9940(10)
_cell_length_c                   13.4560(5)
_cell_measurement_reflns_used    16855
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.9
_cell_measurement_theta_min      1.3
_cell_volume                     2523.3(3)
_computing_data_collection       'Blu-Ice (McPhillips,T.M. et.al. (2002)'
_computing_data_reduction        'XDS (Wabsch, W. (2010)'
_computing_molecular_graphics    'OrtepII (Johnson, C. K. (1976)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Beamline MX2 at the Australian Synchrotron'
_diffrn_measurement_method       '\f scans'
_diffrn_radiation_monochromator  silicon_111
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.71077
_diffrn_reflns_av_R_equivalents  0.1817
_diffrn_reflns_av_sigmaI/netI    0.2194
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16855
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.30
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.005
_exptl_crystal_size_min          0.005
_refine_diff_density_max         1.817
_refine_diff_density_min         -1.408
_refine_diff_density_rms         0.304
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         4267
_refine_ls_number_restraints     141
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.3714
_refine_ls_R_factor_gt           0.2660
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+150.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.5261
_refine_ls_wR_factor_ref         0.5693
_reflns_number_gt                2000
_reflns_number_total             4267
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            c2ob25090j.txt
_cod_data_source_block           asuv1
_cod_original_cell_volume        2523.3(2)
_cod_original_sg_symbol_Hall     '-p 2ybc'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7152320