N-Aminopyrroledione?hydrazonoketene?pyrazolium oxide?pyrazolone rearrangements and pyrazolone tautomerismElectronic supplementary information (ESI) available: calculated and observed IR spectra of 8a and X-ray structure, packing diagram, bond lengths and angles for compound 14. See http://www.rsc.org/suppdata/ob/b3/b304070d
Ebner, Sieglinde; Wallfisch, Bianca; Andraos, John; Aitbaev, Ilyas; Kiselewsky, Michael; Bernhardt, Paul V.; Kollenz, Gert; Wentrup, Curt; Organic & Biomolecular Chemistry 1 (2003) 2550–; doi:10.1039/b304070d

data_7151471
_publ_section_title
;
 N-Aminopyrroledione?hydrazonoketene?pyrazolium oxide?pyrazolone
 rearrangements and pyrazolone tautomerismElectronic supplementary
 information (ESI) available: calculated and observed IR spectra of 8a
 and X-ray structure, packing diagram, bond lengths and angles for
 compound 14. See http://www.rsc.org/suppdata/ob/b3/b304070d
;
_journal_issue                   14
_journal_name_full               'Organic &amp;  Biomolecular Chemistry'
_journal_page_first              2550
_journal_paper_doi               10.1039/b304070d
_journal_volume                  1
_journal_year                    2003
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C11 H13 Cl1 N2 O1'
_chemical_formula_structural     'C11 H13 N2 O CL'
_chemical_formula_sum            'C11 H13 Cl N2 O'
_chemical_formula_weight         224.68
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_audit_conform_dict_location     ftp://ftp.iucr.org/cifdics/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.1
_audit_creation_date             2003-04-07T15:49:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                103.70(2)
_cell_angle_beta                 109.61(2)
_cell_angle_gamma                97.53(2)
_cell_formula_units_Z            2
_cell_length_a                   7.348(2)
_cell_length_b                   8.642(2)
_cell_length_c                   9.832(3)
_cell_measurement_reflns_used    21
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15.548
_cell_measurement_theta_min      10.684
_cell_measurement_wavelength     0.71073
_cell_volume                     556.1(3)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_orient_matrix_type
;
x-axis points to radiation source
the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      -0.107369
_diffrn_orient_matrix_UB_12      -0.89661E-1
_diffrn_orient_matrix_UB_13      -0.7768E-2
_diffrn_orient_matrix_UB_21      -0.06619
_diffrn_orient_matrix_UB_22      -0.14651E-1
_diffrn_orient_matrix_UB_23      -0.110674
_diffrn_orient_matrix_UB_31      0.78269E-1
_diffrn_orient_matrix_UB_32      -0.81995E-1
_diffrn_orient_matrix_UB_33      -0.22528E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2115
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.31
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        10
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.318
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       0.034(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1272
_refine_ls_R_factor_gt           0.0692
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1269P)^2^+0.0721P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1896
_refine_ls_wR_factor_ref         0.2244
_reflns_number_gt                1101
_reflns_number_total             1948
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b304070d.txt
_cod_data_source_block           1986cw10
_cod_database_code               7151471
_diffrn_standards_decay_corr_max 1.154
_diffrn_standards_decay_corr_min 0.996