#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/64/4026481.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_4026481
loop_
_publ_author_name
'Matthew Bancerz'
'Michael K. Georges'
_publ_section_title
;
 Verdazyl Radicals as Substrates for Organic Synthesis: A Synthesis of
 3-Methyl-5-aryl-1,3,4-oxadiazolones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6377
_journal_page_last               6382
_journal_paper_doi               10.1021/jo200820g
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C9 H8 N2 O2'
_chemical_formula_sum            'C9 H8 N2 O2'
_chemical_formula_weight         176.17
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                109.174(4)
_cell_angle_beta                 96.472(5)
_cell_angle_gamma                101.156(5)
_cell_formula_units_Z            2
_cell_length_a                   5.6864(6)
_cell_length_b                   7.6634(10)
_cell_length_c                   10.3029(10)
_cell_measurement_reflns_used    3615
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      2.9
_cell_volume                     408.46(8)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3615
_diffrn_reflns_theta_full        27.62
_diffrn_reflns_theta_max         27.62
_diffrn_reflns_theta_min         2.90
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_description       plate
_exptl_crystal_F_000             184
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1849
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0686P)²+0.0623P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1264
_reflns_number_gt                1414
_reflns_number_total             1849
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo200820g_si_001.cif
_cod_data_source_block           k0960a
_cod_database_code               4026481
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_refinement_flags
O1 O 0.68272(18) 0.71130(15) 0.38052(10) 0.0287(3) Uani 1 1 d .
O2 O 0.71309(19) 0.53703(16) 0.15689(11) 0.0338(3) Uani 1 1 d .
N1 N 0.3661(2) 0.48799(17) 0.25243(12) 0.0261(3) Uani 1 1 d .
N2 N 0.3014(2) 0.56933(17) 0.38067(12) 0.0270(3) Uani 1 1 d .
C1 C 0.4943(2) 0.7011(2) 0.45256(15) 0.0251(3) Uani 1 1 d .
C2 C 0.5955(3) 0.5703(2) 0.24912(15) 0.0268(3) Uani 1 1 d .
C3 C 0.5277(2) 0.8392(2) 0.59361(14) 0.0249(3) Uani 1 1 d .
C4 C 0.3411(3) 0.8302(2) 0.67063(15) 0.0291(4) Uani 1 1 d .
H4A H 0.1952 0.7315 0.6326 0.035 Uiso 1 1 calc R
C5 C 0.3707(3) 0.9660(2) 0.80256(16) 0.0320(4) Uani 1 1 d .
H5A H 0.2444 0.9599 0.8552 0.038 Uiso 1 1 calc R
C6 C 0.5834(3) 1.1117(2) 0.85935(16) 0.0309(4) Uani 1 1 d .
H6A H 0.6017 1.2048 0.9499 0.037 Uiso 1 1 calc R
C7 C 0.7676(3) 1.1202(2) 0.78317(15) 0.0298(4) Uani 1 1 d .
H7A H 0.9129 1.2193 0.8215 0.036 Uiso 1 1 calc R
C8 C 0.7411(3) 0.9844(2) 0.65092(15) 0.0281(3) Uani 1 1 d .
H8A H 0.8687 0.9904 0.5992 0.034 Uiso 1 1 calc R
C9 C 0.1948(3) 0.3388(2) 0.13644(16) 0.0316(4) Uani 1 1 d .
H9A H 0.2455 0.3373 0.0483 0.047 Uiso 1 1 calc R
H9B H 0.0316 0.3627 0.1362 0.047 Uiso 1 1 calc R
H9C H 0.1913 0.2154 0.1462 0.047 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0255(5) 0.0313(6) 0.0255(6) 0.0072(4) 0.0064(4) 0.0024(4)
O2 0.0302(6) 0.0384(7) 0.0299(6) 0.0081(5) 0.0113(5) 0.0061(5)
N1 0.0260(6) 0.0264(6) 0.0227(6) 0.0061(5) 0.0060(5) 0.0030(5)
N2 0.0288(6) 0.0270(7) 0.0247(7) 0.0085(5) 0.0068(5) 0.0059(5)
C1 0.0252(7) 0.0273(7) 0.0255(7) 0.0123(6) 0.0067(6) 0.0070(6)
C2 0.0266(7) 0.0257(7) 0.0269(8) 0.0088(6) 0.0044(6) 0.0054(6)
C3 0.0272(7) 0.0253(8) 0.0224(7) 0.0093(6) 0.0022(6) 0.0071(6)
C4 0.0265(7) 0.0294(8) 0.0289(8) 0.0097(6) 0.0037(6) 0.0033(6)
C5 0.0304(8) 0.0350(9) 0.0298(8) 0.0102(7) 0.0082(6) 0.0076(6)
C6 0.0351(8) 0.0297(8) 0.0251(8) 0.0073(6) 0.0034(6) 0.0075(6)
C7 0.0293(8) 0.0286(8) 0.0288(8) 0.0103(6) 0.0007(6) 0.0036(6)
C8 0.0257(7) 0.0309(8) 0.0270(8) 0.0113(6) 0.0043(6) 0.0046(6)
C9 0.0287(8) 0.0295(8) 0.0287(8) 0.0044(6) 0.0024(6) 0.0020(6)
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
C1 O1 C2 105.62(11)
C2 N1 N2 112.25(12)
C2 N1 C9 125.79(13)
N2 N1 C9 121.88(12)
C1 N2 N1 103.61(12)
N2 C1 O1 113.49(13)
N2 C1 C3 127.99(13)
O1 C1 C3 118.46(12)
O2 C2 N1 130.78(15)
O2 C2 O1 124.20(13)
N1 C2 O1 105.02(12)
C8 C3 C4 119.66(14)
C8 C3 C1 120.48(13)
C4 C3 C1 119.83(13)
C5 C4 C3 119.48(14)
C4 C5 C6 120.80(14)
C7 C6 C5 119.62(15)
C6 C7 C8 120.25(14)
C7 C8 C3 120.19(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3749(16)
O1 C2 1.3879(18)
O2 C2 1.2103(18)
N1 C2 1.3441(19)
N1 N2 1.3881(17)
N1 C9 1.4468(18)
N2 C1 1.2913(18)
C1 C3 1.455(2)
C3 C8 1.395(2)
C3 C4 1.399(2)
C4 C5 1.382(2)
C5 C6 1.394(2)
C6 C7 1.382(2)
C7 C8 1.387(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 456117
