Green Chemistry Strategies Using Crystal-to-Crystal Photoreactions: Stereoselective Synthesis and Decarbonylation of trans-α,α'-Dialkenoylcyclohexanones
Christopher J. Mortko; Miguel A. Garcia-Garibay; Journal of the American Chemical Society 127 (2005) 7994–7995; doi:10.1021/ja0508166

data_4111737
_publ_section_title
;
 Green Chemistry Strategies Using Crystal-to-Crystal Photoreactions:
 Stereoselective Synthesis and Decarbonylation of
 trans-\a,\a'-Dialkenoylcyclohexanones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7994
_journal_page_last               7995
_journal_paper_doi               10.1021/ja0508166
_journal_volume                  127
_journal_year                    2005
_chemical_formula_moiety         'C14 H18 O5'
_chemical_formula_sum            'C14 H18 O5'
_chemical_formula_weight         266.28
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_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            16
_cell_length_a                   25.083(10)
_cell_length_b                   36.373(15)
_cell_length_c                   5.759(2)
_cell_measurement_reflns_used    3445
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.165
_cell_measurement_theta_min      3.247
_cell_volume                     5254(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7987
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9949
_exptl_absorpt_correction_T_min  0.9007
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Bruker)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       parallelipiped
_exptl_crystal_F_000             2272
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         1754
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0312
_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^)+(0.0435P)^2^+2.1503P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0777
_reflns_number_gt                1587
_reflns_number_total             1754
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0508166si20050208_115127.cif
_cod_data_source_block           gg2503sm
_cod_original_sg_symbol_Hall     F2-2d
_cod_database_code               4111737