Synthesis of 1,5-Dioxocanes via the Two-Fold C-O Bond Forming Nucleophilic 4+4-Cyclodimerization of Cycloprop-2-en-1-ylmethanols
Edwards, Andrew Stephen; Bennin, Trevor; Rubina, Marina; Rubin, Michael; RSC Adv.  (2015) –; doi:10.1039/C5RA14077C

data_7221837
_publ_section_title
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 Synthesis of 1,5-Dioxocanes via the Two-Fold C-O Bond Forming
 Nucleophilic 4+4-Cyclodimerization of Cycloprop-2-en-1-ylmethanols
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_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA14077C
_journal_year                    2015
_chemical_formula_sum            'C22 H24 O2'
_chemical_formula_weight         320.41
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_audit_update_record
;
2015-06-22 deposited with the CCDC.
2015-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 116.9270(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.9651(7)
_cell_length_b                   6.1398(2)
_cell_length_c                   15.2881(6)
_cell_measurement_reflns_used    6742
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.63
_cell_measurement_theta_min      3.24
_cell_volume                     1670.87(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Helios multilayer optics'
_diffrn_radiation_source         'Bruker MicroStar microfocus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_sigmaI/netI    0.0129
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7532
_diffrn_reflns_theta_full        66.00
_diffrn_reflns_theta_max         69.35
_diffrn_reflns_theta_min         4.97
_exptl_absorpt_coefficient_mu    0.623
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.873
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Rectangular parallelepiped'
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1507
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+1.3367P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0944
_reflns_number_gt                1484
_reflns_number_total             1507
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra14077c2.cif
_cod_data_source_block           q32c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7221837