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_7152319
_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
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_date             2011-01-18T09:17:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 100.760(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8238(2)
_cell_length_b                   11.0492(3)
_cell_length_c                   16.3885(4)
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.5756
_cell_measurement_theta_min      3.7918
_cell_volume                     1213.93(6)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_molecular_graphics    'OrtepII (Johnson, C. K. (1976)'
_computing_publication_material  'WinGX Farrugia, L. J. (1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4738
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Oxford Diffraction Gemini diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0160134143
_diffrn_orient_matrix_UB_12      -0.0056400863
_diffrn_orient_matrix_UB_13      0.0438660707
_diffrn_orient_matrix_UB_21      0.1044184108
_diffrn_orient_matrix_UB_22      0.0048245384
_diffrn_orient_matrix_UB_23      0.0017833279
_diffrn_orient_matrix_UB_31      -0.0064108658
_diffrn_orient_matrix_UB_32      0.0638358566
_diffrn_orient_matrix_UB_33      0.0037662059
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22968
_diffrn_reflns_theta_full        32
_diffrn_reflns_theta_max         32.63
_diffrn_reflns_theta_min         3.9
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.90627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         4234
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.955
_refine_ls_R_factor_all          0.057
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0707P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1062
_reflns_number_gt                3131
_reflns_number_total             4234
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c2ob25090j.txt
_cod_data_source_block           asuv2
_cod_original_sg_symbol_Hall     '-p 2ybc'
_cod_database_code               7152319