Four-Component Reaction of N-Sulfonylimines, (Cyanomethylene)triphenylphosphorane, Nitromethane, and Formaldehyde for the Synthesis of 3-Substituted 2-Methylene-4-nitrobutanenitriles
Yin-Huan Jin; Fan Fang; Xiang Zhang; Qing-Zhou Liu; Hao-Bo Wang; Shi-Kai Tian; Journal of Organic Chemistry 76 (2011) 4163–4167; doi:10.1021/jo200483n

data_4026320
_publ_section_title
;
 Four-Component Reaction of N-Sulfonylimines,
 (Cyanomethylene)triphenylphosphorane, Nitromethane, and Formaldehyde for
 the Synthesis of 3-Substituted 2-Methylene-4-nitrobutanenitriles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4163
_journal_page_last               4167
_journal_paper_doi               10.1021/jo200483n
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C18 H16 N2 O5 S'
_chemical_formula_weight         372.39
_space_group_IT_number           14
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_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.670(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.2247(16)
_cell_length_b                   8.4060(9)
_cell_length_c                   17.517(3)
_cell_measurement_reflns_used    2489
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      68.2164
_cell_measurement_theta_min      2.6310
_cell_volume                     1865.5(5)
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_collection       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Gemini S Ultra, Oxford Diffraction'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6316
_diffrn_reflns_theta_full        65.07
_diffrn_reflns_theta_max         65.07
_diffrn_reflns_theta_min         5.42
_exptl_absorpt_coefficient_mu    1.815
_exptl_absorpt_correction_T_max  0.5943
_exptl_absorpt_correction_T_min  0.5305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3139
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0798
_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^)+(0.0015P)^2^+2.8704P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1376
_refine_ls_wR_factor_ref         0.1446
_reflns_number_gt                2437
_reflns_number_total             3139
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200483n_si_002.cif
_cod_data_source_block           jyh06-30
_cod_original_cell_volume        1865.4(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4026320