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_4036306
_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_absolute_configuration syn
_chemical_formula_moiety         'C9 H12 N2 O2'
_chemical_formula_sum            'C9 H12 N2 O2'
_chemical_formula_weight         180.21
_chemical_name_systematic
;
 (S)-1-Hydroxy-3-(1-phenylethyl)urea
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2013-04-06
_audit_creation_method
;
  Olex2 1.2-alpha
  (compiled Mar 21 2013 11:16:32, GUI svn.r4446)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.2202(3)
_cell_length_b                   10.5445(5)
_cell_length_c                   25.0280(13)
_cell_measurement_reflns_used    6090
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.57
_cell_measurement_theta_min      2.94
_cell_volume                     1905.47(16)
_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
;
SHELXL-2012, 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 0.999
_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  0.0363
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            20707
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        30.000
_diffrn_reflns_theta_max         30.001
_diffrn_reflns_theta_min         1.627
_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    0.090
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.7373
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2009/1 (Bruker,2010) was used for absorption correction.
wR2(int) was 0.0672 before and 0.0547 after correction.
The Ratio of minimum to maximum transmission is 0.8551.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x calculated using 1855 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61). Absolute 
 configuration cannot be determined reliably.
;
_refine_ls_abs_structure_Flack   -1.0(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         5554
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0531P)^2^+0.1774P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1035
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4710
_reflns_number_total             5554
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01470_si_002.cif
_cod_data_source_block           16
_cod_database_code               4036306
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Uiso(H81A)=Uiso(H82A)=Uiso(H83A)
 Uiso(H81B)=Uiso(H82B)=Uiso(H83B)
3.a Riding coordinates:
 C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C7A(H7A), C2B(H2B),
 C3B(H3B), C4B(H4B), C5B(H5B), C6B(H6B), C7B(H7B)
3.b Rotating group:
 C8A(H81A,H82A,H83A), C8B(H81B,H82B,H83B)
;
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.954
_shelxl_version_number           2013-2