Copper(i)-catalyzed intramolecular [2 + 2] cycloaddition of 1,6-enyne-derived ketenimine: an efficient construction of strained and bridged 7-substituted-3-heterobicyclo[3.1.1]heptan-6-one
Li, Bao-Sheng; Yang, Bin-Miao; Wang, Shao-Hua; Zhang, Yong-Qiang; Cao, Xiao-Ping; Tu, Yong-Qiang; Chemical Science 3 (2012) 1975–; doi:10.1039/c2sc20109g

data_1515179
_publ_section_title
;
 Copper(i)-catalyzed intramolecular [2 + 2] cycloaddition of
 1,6-enyne-derived ketenimine: an efficient construction of strained and
 bridged 7-substituted-3-heterobicyclo[3.1.1]heptan-6-one
;
_journal_issue                   6
_journal_name_full               'Chemical Science'
_journal_page_first              1975
_journal_paper_doi               10.1039/c2sc20109g
_journal_volume                  3
_journal_year                    2012
_chemical_formula_sum            'C12 H12 O3'
_chemical_formula_weight         204.22
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.999(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.846(3)
_cell_length_b                   6.8888(16)
_cell_length_c                   12.417(3)
_cell_measurement_reflns_used    3234
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.80
_cell_measurement_theta_min      3.33
_cell_volume                     997.9(4)
_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  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6968
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         3.33
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9817
_exptl_absorpt_correction_T_min  0.9779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.185(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0939P)^2^+0.1799P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1373
_reflns_number_gt                1567
_reflns_number_total             1857
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2sc20109g.txt
_cod_data_source_block           p21c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1515179