An Experimental and Computational Approach to Understanding the Reactions of Acyl Nitroso Compounds in [4 + 2] Cycloadditions.
Chaiyaveij, Duangduan; Batsanov, Andrei S.; Fox, Mark A.; Marder, Todd B.; Whiting, Andrew; The Journal of organic chemistry 80 (2015) 9518–9534; doi:10.1021/acs.joc.5b01470

data_4036307
_publ_section_title
;
 An Experimental and Computational Approach to Understanding the Reactions
 of Acyl Nitroso Compounds in [4 + 2] Cycloadditions.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9518
_journal_page_last               9534
_journal_paper_doi               10.1021/acs.joc.5b01470
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C14 H15 N O2'
_chemical_formula_sum            'C14 H15 N O2'
_chemical_formula_weight         229.27
_chemical_melting_point          348
_chemical_name_systematic
;
 2-Oxa-3-azabicyclo[2.2.2]oct-5-en-3-yl)-2-phenyl-ethanone 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-03-30
_audit_creation_method
;
  Olex2 1.1-beta
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.428(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.7130(10)
_cell_length_b                   5.8495(5)
_cell_length_c                   14.8249(12)
_cell_measurement_reflns_used    7245
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.980
_cell_measurement_theta_min      2.235
_cell_volume                     1169.53(17)
_computing_cell_refinement       'SAINT v7.46A (Bruker, 2008)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v7.46A (Bruker, 2008)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122
;
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20862
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.51
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3411
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0668
_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^)+(0.0736P)^2^+0.6610P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1720
_refine_ls_wR_factor_ref         0.1847
_reflns_number_gt                2722
_reflns_number_total             3411
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo5b01470_si_002.cif
_cod_data_source_block           17
_cod_original_cell_volume        1169.53(16)
_cod_database_code               4036307