An NMR and X-ray study of the structure of the azo coupling product of 4-dimethylaminopent-3-en-2-one and benzenediazonium-tetrafluoroborate
Petr Šim°unek; Valerio Bertolasi; Antonín Lyčka; Vladimír Macháček; Org. Biomol. Chem. 1 (2003) 3250–3256; doi:10.1039/b303206j

data_7151437
_publ_section_title
;
 An NMR and X-ray study of the structure of the azo coupling product of
 4-dimethylaminopent-3-en-2-one and benzenediazonium-tetrafluoroborate
;
_journal_issue                   18
_journal_name_full               'Org. Biomol. Chem.'
_journal_page_first              3250
_journal_page_last               3256
_journal_paper_doi               10.1039/b303206j
_journal_volume                  1
_journal_year                    2003
_chemical_formula_moiety         'C19 H21 N5 O'
_chemical_formula_sum            'C19 H21 N5 O'
_chemical_formula_weight         335.41
_chemical_name_systematic
;
(3E,4E)-4-(dimethylamino)-5-[(E)-phenyldiazenyl]pent-4-ene-2,3-dione 
3-(phenylhydrazone)
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.8290(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5524(2)
_cell_length_b                   10.8377(2)
_cell_length_c                   16.4357(4)
_cell_measurement_reflns_used    8623
_cell_measurement_temperature    295
_cell_measurement_theta_max      28
_cell_measurement_theta_min      3.43
_cell_volume                     1839.73(7)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Kappa CCd server software (Nonius, 1997)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP II (Johnson, 1976)'
_computing_publication_material
;
SHELXL-97 (Sheldrick, 1997); PARST (Nardelli, 1995)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et. al. 1994)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius Kappa CCd'
_diffrn_measurement_method       '\f scans and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8623
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         3.43
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4414
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0540
_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^)+(0.0666P)^2^+0.3977P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1634
_reflns_number_gt                2987
_reflns_number_total             4414
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            b303206j.txt
_cod_data_source_block           (1)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7151437