Ring opening of pyridines: the pseudo-<i>cis</i> and pseudo-<i>trans</i> isomers of tetra-<i>n</i>-butylammonium 4-nitro-5-oxo-2-pentenenitrilate
Zeller, Matthias; Pett, Virginia B.; Haynes, LeRoy W.; Acta Crystallographica Section C 63 (2007) o343–o346; doi:10.1107/S0108270107019506

data_2016000
_publ_section_title
;
 Ring opening of pyridines: the pseudo-<i>cis</i> and
 pseudo-<i>trans</i> isomers of tetra-<i>n</i>-butylammonium
 4-nitro-5-oxo-2-pentenenitrilate
;
_journal_coeditor_code           LN3045
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o343
_journal_page_last               o346
_journal_paper_doi               10.1107/S0108270107019506
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C16 H36 N +, C5 H3 N2 O3 -'
_chemical_formula_moiety         'C16 H36 N +, C5 H3 N2 O3 -'
_chemical_formula_sum            'C21 H39 N3 O3'
_chemical_formula_weight         381.55
_chemical_name_systematic
;
tetra-<i>n</i>-butylammonium 4-nitro-5-oxo-2-pentenenitrilate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 95.894(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7894(9)
_cell_length_b                   18.3872(16)
_cell_length_c                   12.2327(11)
_cell_measurement_reflns_used    7740
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.54
_cell_measurement_theta_min      2.54
_cell_volume                     2190.2(3)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEX CCD diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18699
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS in SAINT-Plus; Bruker, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.73
_exptl_crystal_size_mid          0.59
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.180
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         5402
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.186
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0579
_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^)+(0.046P)^2^+1.24P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1358
_reflns_number_gt                4809
_reflns_number_total             5402
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ln3045.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2016000
_cod_database_fobs_code          2016000