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_4036301
_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         'C7 H8 N2 O2'
_chemical_formula_sum            'C7 H8 N2 O2'
_chemical_formula_weight         152.15
_chemical_name_systematic
;
 1-hydroxy-3-phenylurea 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-04-30
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                94.598(18)
_cell_angle_beta                 90.430(18)
_cell_angle_gamma                110.027(16)
_cell_formula_units_Z            4
_cell_length_a                   5.3049(4)
_cell_length_b                   5.9648(5)
_cell_length_c                   24.0989(18)
_cell_measurement_reflns_used    2885
_cell_measurement_temperature    120
_cell_measurement_theta_max      0.000
_cell_measurement_theta_min      0.000
_cell_volume                     713.64(12)
_computing_cell_refinement       'SAINT v7.46A (Bruker, 2008)'
_computing_data_collection       'SMART v5.630 (Bruker, 2003)'
_computing_data_reduction        'SAINT v7.46A (Bruker, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_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  0.0620
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8767
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         0.85
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9936
_exptl_absorpt_correction_T_min  0.9729
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2514
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0504P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0962
_reflns_number_gt                1856
_reflns_number_total             2514
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo5b01470_si_002.cif
_cod_data_source_block           2
_cod_original_cell_volume        713.64(10)
_cod_database_code               4036301
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H3A(0.03) H4A(0.033) H5A(0.035) H6A(0.036) H7A(0.033) H3B(0.03)
 H4B(0.032) H5B(0.034) H6B(0.034) H7B(0.031)
 Fixed X: H3A(0.6514) H4A(0.2586) H5A(0.0271) H6A(0.1964) H7A(0.5863)
 H3B(0.2136) H4B(-0.1605) H5B(-0.392) H6B(-0.2447) H7B(0.1248)
 Fixed Y: H3A(0.7241) H4A(0.5441) H5A(0.1324) H6A(-0.0997) H7A(0.0798)
 H3B(0.8462) H4B(0.7031) H5B(0.2904) H6B(0.0241) H7B(0.1646)
 Fixed Z: H3A(0.3361) H4A(0.2811) H5A(0.2803) H6A(0.3329) H7A(0.3888)
 H3B(0.1655) H4B(0.2199) H5B(0.2198) H6B(0.1645) H7B(0.1093)
;
_olex2_submission_special_instructions 'No special instructions were received'