Use of allene in 1,3-dipolar addition to a carbonyl ylide: syntheses of 3-hydroxy-cis-nemorensic acid and nemorensic acid.
Hodgson, David M; Le Strat, Frédéric; Chemical communications (Cambridge, England)  (2004) 822–823; doi:10.1039/b316908a

data_7102550
_publ_section_title
;
 Use of allene in 1,3-dipolar addition to a carbonyl ylide: syntheses
 of 3-hydroxy-cis-nemorensic acid and nemorensic acid.
;
_journal_issue                   7
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              822
_journal_page_last               823
_journal_paper_doi               10.1039/b316908a
_journal_year                    2004
_chemical_compound_source
;
synthesis as described
;
_chemical_formula_moiety         ' C12 H18 O4 '
_chemical_formula_sum            'C12 H18 O4'
_chemical_formula_weight         226.27
_chemical_melting_point          350.15
_chemical_name_common
;
(1'R*,5'R*,7'R*)-dispiro(1,3-dioxolane-2,2'-(1',5'-dimethyl-
8'-oxa-bicyclo(3.2.1)octane)-7',2''-oxirane)
;
_chemical_name_systematic
;
[1'R*,5'R*,7'R*]-dispiro[1,3-dioxolane-2,2'-(1',5'-dimethyl-8'-oxa-
bicyclo[3.2.1]octane)-7',2''-oxirane]

;
_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
_cell_angle_alpha                90
_cell_angle_beta                 99.5173(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7237(3)
_cell_length_b                   8.2796(2)
_cell_length_c                   10.8451(2)
_cell_measurement_reflns_used    11736
_cell_measurement_temperature    150
_cell_measurement_theta_max      28
_cell_measurement_theta_min      5
_cell_volume                     1126.8
_computing_cell_refinement
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_data_collection
;
KappaCCD software 'Collect' (Nonius, 2000)
;
_computing_data_reduction
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_publication_material
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_refinement
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
Nonius KappaCCD
;
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11736
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         5.19
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_exptl_crystal_colour            ' colourless '
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       ' fragment '
_exptl_crystal_F_000             488
_exptl_crystal_preparation       ' 10% CH2Cl2:petrol '
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.28
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0276
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1914
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.011630
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Chebychev polynomial with 3 parameters (Carruthers & Watkin , 1979)
1.39    0.752    0.881
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0549
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                1914
_reflns_number_total             2548
_reflns_threshold_expression     >3.00\s(I)
_cod_data_source_file            b316908a.txt
_cod_data_source_block           ARC557
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '77C' was changed to '350.15' - it
was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_original_formula_sum        ' C12 H18 O4 '
_cod_database_code               7102550