Butadienic Building Blocks from 2-Nitrothiophene as Precursors of Nitrogen Heterocycles: Intriguing Dichotomic Behavior
Lara Bianchi; Gianluca Giorgi; Massimo Maccagno; Giovanni Petrillo; Valeria Rocca; Fernando Sancassan; Carlo Scapolla; Elda Severi; Cinzia Tavani; Journal of Organic Chemistry 72 (2007) 9067–9073; doi:10.1021/jo701460k

data_4023014
_publ_contact_author_address
; Dept of Chemistry
  Universit\`a degli Studi di Siena
  Via Aldo Moro
  I-53100 Siena
  Italy
;
_publ_contact_author_email       gianluca.giorgi@unisi.it
_publ_contact_author_fax         '+39 0577 234241'
_publ_contact_author_name        'Gianluca Giorgi, Ph. D.'
_publ_contact_author_phone       '+39 0577 234233'
_publ_section_title
;
 Butadienic Building Blocks from 2-Nitrothiophene as Precursors
 of Nitrogen Heterocycles: Intriguing Dichotomic Behavior
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9067
_journal_page_last               9073
_journal_paper_doi               10.1021/jo701460k
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C12 H13 N3 O2 S'
_chemical_formula_sum            'C12 H13 N3 O2 S'
_chemical_formula_weight         263.31
_chemical_name_systematic
;
(3S,4S,E)-3-(methylthio)-3-nitro-4-styryl-4,5-dihydro-3H-pyrazole
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 104.882(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.0745(3)
_cell_length_b                   10.6010(5)
_cell_length_c                   9.9223(5)
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     617.52(5)
_computing_cell_refinement
;
        'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' 
;
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
;
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' 
;
_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    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0643
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7697
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         3.47
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2804
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0408
_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^)+(0.0321P)^2^+0.0838P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0849
_reflns_number_gt                2305
_reflns_number_total             2805
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701460k-File001.cif
_cod_data_source_block           petr05
_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      'P 21'
_cod_database_code               4023014