Strained to the limit: when a cyclobutyl moiety becomes a thermodynamic sink in a protolytic ring-opening of photogenerated oxetanes.
Valiulin, Roman A.; Arisco, Teresa M.; Kutateladze, Andrei G.; Organic letters 12 (2010) 3398–3401; doi:10.1021/ol101297b

data_1503096
_publ_section_title
;
 Strained to the limit: when a cyclobutyl moiety becomes a thermodynamic
 sink in a protolytic ring-opening of photogenerated oxetanes.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3398
_journal_page_last               3401
_journal_paper_doi               10.1021/ol101297b
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C12 H17 Cl O'
_chemical_formula_sum            'C12 H17 Cl O'
_chemical_formula_weight         212.71
_chemical_name_common            1,3-chlorohydrine
_chemical_name_systematic
;
10-chlorotetracyclo[5.3.1.1^9,11^.0^1,6^]dodecan-12-ol
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.201(8)
_cell_angle_beta                 96.264(8)
_cell_angle_gamma                115.471(5)
_cell_formula_units_Z            6
_cell_length_a                   10.9259(15)
_cell_length_b                   11.4009(16)
_cell_length_c                   14.825(3)
_cell_measurement_reflns_used    9750
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      45.96
_cell_measurement_theta_min      2.78
_cell_volume                     1604.8(5)
_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      296(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 APEX II Diffractometer'
_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  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0690
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            35462
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         1.43
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.636
_refine_diff_density_min         -0.931
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         9733
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0652P)^2^+0.6108P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1119
_reflns_number_gt                7721
_reflns_number_total             9733
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101297b_si_004.cif
_cod_data_source_block           57_oxetane_bn
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1503096