General Route for Preparing β-Nitrocarbonyl Compounds Using Copper Thermal Redox Catalysis.
Gietter, Amber A. S.; Gildner, Peter G.; Cinderella, Andrew P.; Watson, Donald A.; Organic letters 16 (2014) 3166–3169; doi:10.1021/ol5014153

data_1516340
_publ_section_title
;
 General Route for Preparing \b-Nitrocarbonyl Compounds Using Copper
 Thermal Redox Catalysis.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              3166
_journal_page_last               3169
_journal_paper_doi               10.1021/ol5014153
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration syn
_chemical_formula_sum            'C7 H11 N O4'
_chemical_formula_weight         173.17
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8815(3)
_cell_length_b                   8.9902(4)
_cell_length_c                   15.9025(7)
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      73.54
_cell_measurement_theta_min      5.56
_cell_volume                     840.86(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35962
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.258
_diffrn_reflns_theta_min         5.564
_exptl_absorpt_coefficient_mu    0.964
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX2 (Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.249
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.128
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
; 
 Flack x determined using 655 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.49(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1700
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0269
_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^)+(0.0450P)^2^+0.0996P] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0772
_reflns_Friedel_coverage         0.672
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                1634
_reflns_number_total             1700
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5014153_si_002.cif
_cod_data_source_block           donw032
_cod_depositor_comments
'Adding full bibliography for 1516339--1516342.cif.'
_cod_database_code               1516340
_shelx_estimated_absorpt_t_min   0.795
_shelx_estimated_absorpt_t_max   0.887
_shelxl_version_number           2013-2
_shelx_res_checksum              4454
_shelx_hkl_checksum              89418