Spiro-fused (C2)-Azirino-(C4)-Pyrazolones - a New Heterocyclic System, Synthesis, Spectroscopic Studies and X-Ray Structure Analysis
Wolfgang Holzer; Rosa M. Claramunt; Marta Pérez-Torralba; Davide Guggi; Thomas H. Brehmer; Journal of Organic Chemistry 68 (2003) 7943–7950; doi:10.1021/jo030131t

data_4022378
_publ_contact_author
;                                                                              
      Wolfgang Holzer
      Institut f\"ur Pharmazeutische Chemie
      University of Vienna, Pharmaziezentrum
      Althan str. 14
      A-1090 Vienna
      Austria
;
_publ_contact_author_email       wolfgang.holzer@merian.pch.univie.ac.at
_publ_contact_author_fax         '+43 1 4277 9551 '
_publ_contact_author_phone       '+43 1 4277 8023'
_publ_section_title
;
Spiro-fused (C2)-Azirino-(C4)-Pyrazolones - a New Heterocyclic System,
Synthesis, Spectroscopic Studies and X-Ray Structure Analysis
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7943
_journal_page_last               7950
_journal_paper_doi               10.1021/jo030131t
_journal_volume                  68
_journal_year                    2003
_chemical_formula_moiety         'C18 H15 N3 O'
_chemical_formula_sum            'C18 H15 N3 O'
_chemical_formula_weight         289.33
_chemical_melting_point          377.15
_chemical_name_common            spiro
_chemical_name_systematic
;
1-benzyl-7-methyl-2-phenyl-1,5,6-triazaspiro[2,4]hepta-1,6-dien-4-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   'electron difference map'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             00-01-20
_audit_creation_method           SHELXL-97
_audit_update_record
' 00-02-03   text and data added by Thomas H. Brehmer'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.8250(2)
_cell_length_b                   10.7660(4)
_cell_length_c                   29.5020(11)
_cell_measurement_temperature    200(2)
_cell_volume                     1532.51(10)
_computing_cell_refinement       'Denzo-SMN (Nonius, 1997)'
_computing_data_collection       'Denzo-SMN (Nonius, 1997)'
_computing_data_reduction        'Denzo-SMN (Nonius, 1997)'
_computing_molecular_graphics    'DIAMOND 2.1a (Klaus Brandenburg, 1999)'
_computing_publication_material  'LOTUS WORD PRO 97'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et.al, 1993)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 0.1
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Enraf Kappa CCD diffractometer'
_diffrn_measurement_method       'phi and omega 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            3038
_diffrn_reflns_theta_full        26.34
_diffrn_reflns_theta_max         26.34
_diffrn_reflns_theta_min         2.34
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'sqare base column'
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.109
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(18)
_refine_ls_extinction_coef       0.020(2)
_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     260
_refine_ls_number_reflns         3038
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0285P)^2^+0.2062P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0832
_reflns_number_gt                2499
_reflns_number_total             3038
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo030131t_2.cif
_cod_data_source_block           4h
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '104 deg C' was changed to '377.15' -
it was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not determined' was changed to
'?' - the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4022378