Structure of a 4-Nitroso-5-aminopyrazole and Its Salts: Tautomerism, Protonation, and E/Z Isomerism
Marcus H. Holschbach; Dionisia Sanz; Rosa M. Claramunt; Lourdes Infantes; Sam Motherwell; Paul R. Raithby; María Luisa Jimeno; David Herrero; Ibon Alkorta; Nadine Jagerovic; José Elguero; Journal of Organic Chemistry 68 (2003) 8831–8837; doi:10.1021/jo034833u

data_4022530
_publ_contact_author
;     Lourdes Infantes
       Cambridge Crystallographic Data Centre
       12 Union Rd
       Cambridge CB2 1EZ
       UK
;
_publ_contact_author_email       lourdes@ccdc.cam.ac
_publ_section_title
;
 Structure of a 4-Nitroso-5-aminopyrazole and Its Salts:
 Tautomerism, Protonation, and E/Z Isomerism
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8831
_journal_page_last               8837
_journal_paper_doi               10.1021/jo034833u
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C10 H10 N4 O'
_chemical_formula_weight         202.22
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 99.376(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.4700(6)
_cell_length_b                   23.896(3)
_cell_length_c                   9.3400(13)
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      2.91
_cell_volume                     984.3(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 19'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker Nonius Kappa CCD'
_diffrn_measurement_method       'Omega and phi 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  0.0634
_diffrn_reflns_av_sigmaI/netI    0.0761
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2475
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         4.07
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.011
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sortav (Blessing, 1995)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(2)
_refine_ls_extinction_coef       0.086(9)
_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   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1499
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0461
_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^)+(0.0330P)^2^+0.2745P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1078
_reflns_number_gt                1311
_reflns_number_total             1499
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo034833usi20030620_020324.cif
_cod_data_source_block           h03prr18
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4022530