Variants of the Prins cyclization for the synthesis of terpenoid spiroethers and oxabicyclo[3.3.1]nonane-derivatives.
Weidmann, Verena; Ploog, Jasper; Kliewer, Serge; Schaffrath, Mathias; Maison, Wolfgang; The Journal of organic chemistry 79 (2014) 10123–; doi:10.1021/jo501755x

data_4030096
_publ_section_title
;
 Variants of the Prins cyclization for the synthesis of terpenoid
 spiroethers and oxabicyclo[3.3.1]nonane-derivatives.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10123
_journal_paper_doi               10.1021/jo501755x
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C15 H20 O2'
_chemical_formula_sum            'C15 H20 O2'
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_chemical_melting_point          364.6(15)
_chemical_name_systematic
; 
3-methoxy-1,9-dimethyl-10-oxatricyclo[7.3.1.0]-trideca-2,4,6-triene 
;
_space_group_IT_number           14
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_molecular_graphics    mercury
_computing_publication_material  SHELXL
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_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4127
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
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_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1113
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21571
_diffrn_reflns_theta_full        76.44
_diffrn_reflns_theta_max         76.44
_diffrn_reflns_theta_min         5.37
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
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_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  0.9504
_exptl_absorpt_correction_T_min  0.8306
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_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
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_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
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_refine_ls_number_reflns         2570
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0834
_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^)+(0.1801P)^2^+0.1450P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2106
_refine_ls_wR_factor_ref         0.2267
_reflns_number_gt                2251
_reflns_number_total             2570
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501755x_si_003.cif
_cod_data_source_block           sw03
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '90-93 C' was changed to '364.6(15)'
- it was converted from degrees Celsius(C) to Kelvins(K), the average
value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 4030095--4030097.cif.

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1226.20(8)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4030096