Copper(II)-catalyzed room temperature aerobic oxidation of hydroxamic acids and hydrazides to acyl-nitroso and azo intermediates, and their Diels-Alder trapping.
Chaiyaveij, Duangduan; Cleary, Leah; Batsanov, Andrei S.; Marder, Todd B.; Shea, Kenneth J.; Whiting, Andrew; Organic letters 13 (2011) 3442–3445; doi:10.1021/ol201188d

data_1502252
_publ_section_title
;
 Copper(II)-catalyzed room temperature aerobic oxidation of hydroxamic
 acids and hydrazides to acyl-nitroso and azo intermediates, and their
 Diels-Alder trapping.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3442
_journal_page_last               3445
_journal_paper_doi               10.1021/ol201188d
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C14 H15 N O3'
_chemical_formula_sum            'C14 H15 N O3'
_chemical_formula_weight         245.27
_chemical_melting_point          350(1)
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                65.453(6)
_cell_angle_beta                 88.454(6)
_cell_angle_gamma                84.712(7)
_cell_formula_units_Z            2
_cell_length_a                   6.0126(3)
_cell_length_b                   10.4102(5)
_cell_length_c                   10.6716(5)
_cell_measurement_reflns_used    7443
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.99
_cell_measurement_theta_min      2.16
_cell_volume                     604.96(6)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement
'A short history of SHELX (Sheldrick, 2008)/Bruker'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2008)/Bruker'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.098254
_diffrn_orient_matrix_UB_12      0.046873
_diffrn_orient_matrix_UB_13      -0.083819
_diffrn_orient_matrix_UB_21      0.056942
_diffrn_orient_matrix_UB_22      -0.074345
_diffrn_orient_matrix_UB_23      -0.032186
_diffrn_orient_matrix_UB_31      -0.122327
_diffrn_orient_matrix_UB_32      -0.059347
_diffrn_orient_matrix_UB_33      0.050608
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_refln_scan_width         0.3
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11016
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.10
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3525
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0628P)^2^+0.1250P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1154
_reflns_number_gt                3209
_reflns_number_total             3525
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol201188d_si_001.cif
_cod_data_source_block           4b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        604.96(5)
_cod_database_code               1502252