#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/23/4022378.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4022378
loop_
_publ_author_name
'Wolfgang Holzer'
'Rosa M. Claramunt'
'Marta Pérez-Torralba'
'Davide Guggi'
'Thomas H. Brehmer'
_publ_contact_author
;                                                                              
      Wolfgang Holzer
      Institut für 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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0285P)²+0.2062P] where P=(Fo²+2Fc²)/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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
N1 N 0.1249(3) 0.37599(11) 0.42297(4) 0.0463(4) Uani 1 1 d
N2 N -0.0660(3) 0.43741(12) 0.45123(4) 0.0485(3) Uani 1 1 d
N3 N 0.2239(4) 0.69098(13) 0.38449(6) 0.0700(5) Uani 1 1 d
O1 O 0.3897(3) 0.41621(11) 0.35976(4) 0.0701(4) Uani 1 1 d
C1 C -0.2674(6) 0.6438(2) 0.45856(8) 0.0666(6) Uani 1 1 d
C2 C -0.0972(4) 0.54826(14) 0.43522(5) 0.0472(4) Uani 1 1 d
C3 C 0.0698(4) 0.56614(13) 0.39439(6) 0.0482(4) Uani 1 1 d
C4 C 0.2208(4) 0.44664(15) 0.38864(6) 0.0501(4) Uani 1 1 d
C5 C 0.0375(4) 0.65779(14) 0.35783(6) 0.0547(5) Uani 1 1 d
C6 C -0.0947(4) 0.68917(15) 0.31531(6) 0.0504(4) Uani 1 1 d
C7 C -0.0179(5) 0.79570(18) 0.29179(8) 0.0707(6) Uani 1 1 d
C8 C -0.1410(6) 0.8221(2) 0.25100(8) 0.0759(7) Uani 1 1 d
C9 C -0.3355(6) 0.7453(2) 0.23346(8) 0.0760(7) Uani 1 1 d
C10 C -0.4113(6) 0.6406(2) 0.25622(7) 0.0808(7) Uani 1 1 d
C11 C -0.2918(4) 0.61155(18) 0.29733(6) 0.0592(5) Uani 1 1 d
C12 C -0.0003(3) 0.15416(13) 0.41970(5) 0.0395(4) Uani 1 1 d
C13 C -0.0751(5) 0.14086(17) 0.37491(6) 0.0615(5) Uani 1 1 d
C14 C -0.2657(6) 0.0502(2) 0.36270(8) 0.0811(7) Uani 1 1 d
C15 C -0.3798(5) -0.02594(17) 0.39511(10) 0.0781(7) Uani 1 1 d
C16 C -0.3056(5) -0.01256(17) 0.43897(9) 0.0715(6) Uani 1 1 d
C17 C -0.1185(4) 0.07669(14) 0.45120(6) 0.0546(5) Uani 1 1 d
C18 C 0.2089(4) 0.24939(15) 0.43384(7) 0.0492(4) Uani 1 1 d
H1A H -0.403(5) 0.680(2) 0.4375(8) 0.092(7) Uiso 1 1 d
H1B H -0.152(6) 0.711(2) 0.4656(8) 0.104(9) Uiso 1 1 d
H1C H -0.339(6) 0.609(2) 0.4847(9) 0.109(9) Uiso 1 1 d
H7 H 0.108(5) 0.846(2) 0.3070(7) 0.086(7) Uiso 1 1 d
H8 H -0.085(5) 0.891(2) 0.2354(7) 0.092(7) Uiso 1 1 d
H9 H -0.414(5) 0.7715(18) 0.2056(7) 0.084(7) Uiso 1 1 d
H10 H -0.551(6) 0.582(2) 0.2433(8) 0.125(10) Uiso 1 1 d
H11 H -0.338(4) 0.5386(17) 0.3134(6) 0.067(6) Uiso 1 1 d
H13 H 0.010(4) 0.1999(18) 0.3537(6) 0.075(6) Uiso 1 1 d
H14 H -0.313(6) 0.045(2) 0.3321(8) 0.121(9) Uiso 1 1 d
H15 H -0.513(6) -0.087(2) 0.3859(8) 0.111(8) Uiso 1 1 d
H16 H -0.394(6) -0.070(2) 0.4623(8) 0.116(8) Uiso 1 1 d
H17 H -0.061(4) 0.0854(17) 0.4845(7) 0.077(6) Uiso 1 1 d
H18A H 0.379(4) 0.2356(17) 0.4165(6) 0.067(6) Uiso 1 1 d
H18B H 0.242(4) 0.2468(15) 0.4671(6) 0.058(5) Uiso 1 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C4 N1 N2 113.87(13)
C4 N1 C18 126.66(15)
N2 N1 C18 119.41(14)
C2 N2 N1 107.08(13)
C5 N3 C3 61.87(11)
C2 C1 H1A 110.6(13)
C2 C1 H1B 108.1(16)
H1A C1 H1B 103.0(18)
C2 C1 H1C 108.0(16)
H1A C1 H1C 116(2)
H1B C1 H1C 111(2)
N2 C2 C3 111.00(14)
N2 C2 C1 122.31(17)
C3 C2 C1 126.55(16)
C2 C3 C5 129.38(15)
C2 C3 C4 104.48(13)
C5 C3 C4 123.25(15)
C2 C3 N3 121.96(14)
C5 C3 N3 48.42(10)
C4 C3 N3 119.26(15)
O1 C4 N1 126.91(16)
O1 C4 C3 129.56(16)
N1 C4 C3 103.52(14)
N3 C5 C6 142.90(16)
N3 C5 C3 69.71(13)
C6 C5 C3 147.07(16)
C11 C6 C7 119.59(18)
C11 C6 C5 119.88(15)
C7 C6 C5 120.50(18)
C8 C7 C6 119.5(2)
C8 C7 H7 126.1(13)
C6 C7 H7 114.3(13)
C9 C8 C7 120.6(2)
C9 C8 H8 120.6(14)
C7 C8 H8 118.8(15)
C8 C9 C10 120.2(2)
C8 C9 H9 115.4(13)
C10 C9 H9 124.4(13)
C9 C10 C11 120.6(2)
C9 C10 H10 121.0(15)
C11 C10 H10 118.4(15)
C6 C11 C10 119.45(19)
C6 C11 H11 118.5(11)
C10 C11 H11 122.1(12)
C17 C12 C13 118.52(16)
C17 C12 C18 120.48(15)
C13 C12 C18 121.00(16)
C12 C13 C14 119.71(19)
C12 C13 H13 115.8(11)
C14 C13 H13 124.5(11)
C15 C14 C13 120.3(2)
C15 C14 H14 122.8(17)
C13 C14 H14 116.9(17)
C16 C15 C14 119.8(2)
C16 C15 H15 121.7(15)
C14 C15 H15 118.5(15)
C15 C16 C17 120.2(2)
C15 C16 H16 118.2(14)
C17 C16 H16 121.6(14)
C16 C17 C12 121.52(19)
C16 C17 H17 119.6(11)
C12 C17 H17 118.8(11)
N1 C18 C12 113.03(14)
N1 C18 H18A 105.1(11)
C12 C18 H18A 108.4(11)
N1 C18 H18B 106.7(10)
C12 C18 H18B 111.3(10)
H18A C18 H18B 112.2(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C4 1.349(2)
N1 N2 1.4072(18)
N1 C18 1.458(2)
N2 C2 1.2922(19)
N3 C5 1.247(2)
N3 C3 1.564(2)
O1 C4 1.224(2)
C1 C2 1.485(3)
C1 H1A 0.98(3)
C1 H1B 0.94(3)
C1 H1C 0.93(3)
C2 C3 1.462(2)
C3 C5 1.470(2)
C3 C4 1.488(2)
C5 C6 1.447(2)
C6 C11 1.373(3)
C6 C7 1.391(2)
C7 C8 1.372(3)
C7 H7 0.93(2)
C8 C9 1.353(3)
C8 H8 0.92(2)
C9 C10 1.362(3)
C9 H9 0.95(2)
C10 C11 1.379(3)
C10 H10 1.00(3)
C11 H11 0.945(18)
C12 C17 1.373(2)
C12 C13 1.377(2)
C12 C18 1.498(2)
C13 C14 1.389(3)
C13 H13 0.98(2)
C14 C15 1.374(3)
C14 H14 0.93(2)
C15 C16 1.350(3)
C15 H15 0.96(3)
C16 C17 1.367(3)
C16 H16 1.02(3)
C17 H17 1.026(19)
C18 H18A 0.98(2)
C18 H18B 0.994(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21176850
