Tandem Prins/Wagner/Ritter process for the stereoselective synthesis of (3-oxabicyclo[4.2.0]octanyl)amide and (1-(5-aryltetrahydrofuran-3-yl)cyclobutyl)amide derivatives.
Subba Reddy, B. V.; Muralikrishna, K.; Yadav, J. S.; Babu, N. Jagdeesh; Sirisha, K.; Sarma, A. V. S.; Organic & biomolecular chemistry 13 (2015) 5532–5536; doi:10.1039/c5ob00031a

data_7154415
_publ_section_title
;
 Tandem Prins/Wagner/Ritter process for the stereoselective synthesis of
 (3-oxabicyclo[4.2.0]octanyl)amide and
 (1-(5-aryltetrahydrofuran-3-yl)cyclobutyl)amide derivatives.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5532
_journal_page_last               5536
_journal_paper_doi               10.1039/c5ob00031a
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C21 H20 F3 N O2'
_chemical_formula_sum            'C21 H20 F3 N O2'
_chemical_formula_weight         375.38
_chemical_name_systematic
;
N-{4-[4-(trifluoromethyl)phenyl]-3-oxabicyclo[4.2.0]octan-1-yl}benzamide
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-06-19 deposited with the CCDC.
2015-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.212(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.9345(13)
_cell_length_b                   22.9721(13)
_cell_length_c                   10.3059(7)
_cell_measurement_reflns_used    3299
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.45
_cell_measurement_theta_min      2.25
_cell_volume                     3808.4(4)
_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      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18217
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9959
_exptl_absorpt_correction_T_min  0.9676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.244
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3346
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.293
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0978
_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^)+(0.0605P)^2^+5.3381P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1977
_refine_ls_wR_factor_ref         0.2084
_reflns_number_gt                2715
_reflns_number_total             3346
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob00031a2.cif
_cod_data_source_block           av66
_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 3143 2015-03-26 13:38:13Z robertas 

 Adding full bibliography for 7154415.cif.
;
_cod_original_sg_symbol_H-M      'C2/c  '
_cod_database_code               7154415