# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Guoping Yong'
_publ_contact_author_email       gpyong@ustc.edu.cn

_publ_section_title              
;
From zwitterionic radical to neutral radical
with unusual magnetic properties: First K-promoted air oxidative
ring opening reaction of aromatic N-heterocycle
;
loop_
_publ_author_name
'Guoping Yong.'
'Yimen Zhang'
'Chongfu Li.'
'Yingzhou Li.'
'Yongshou Li'
'Wenlong She'

# Attachment '- Compd2.cif'

data_1
_database_code_depnum_ccdc_archive 'CCDC 764965'

#TrackingRef '- Compd2.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H10 N4 O2'
_chemical_formula_weight         266.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   27.0027(16)
_cell_length_b                   3.8705(2)
_cell_length_c                   11.6121(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1213.63(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1873
_cell_measurement_theta_min      3.2699
_cell_measurement_theta_max      62.6935

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.788
_exptl_absorpt_correction_T_max  0.803
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET)
(compiled Aug 27 2009,17:19:36)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2353
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         62.81
_reflns_number_total             1359
_reflns_number_gt                1249
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0331P)^2^+0.9850P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(6)
_refine_ls_number_reflns         1359
_refine_ls_number_parameters     185
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1061
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.85630(10) 0.7766(10) 0.1347(2) 0.0706(9) Uani 1 1 d . . .
N1 N 0.72535(10) 0.3685(8) 0.3347(2) 0.0447(8) Uani 1 1 d . . .
N2 N 0.76365(11) 0.4581(9) 0.1658(3) 0.0538(8) Uani 1 1 d . . .
N3 N 0.91219(12) 1.0348(10) 0.2974(3) 0.0537(8) Uani 1 1 d D . .
O1 O 0.86073(10) 0.8039(9) 0.4337(3) 0.0662(8) Uani 1 1 d . . .
C14 C 0.68842(13) 0.2527(11) 0.4068(3) 0.0536(10) Uani 1 1 d . . .
H14 H 0.6906 0.2829 0.4861 0.064 Uiso 1 1 calc R . .
C11 C 0.68159(14) 0.1627(12) 0.1683(4) 0.0587(11) Uani 1 1 d . . .
H11 H 0.6788 0.1308 0.0892 0.070 Uiso 1 1 calc R . .
C8 C 0.79187(12) 0.5824(10) 0.2551(3) 0.0451(9) Uani 1 1 d . . .
C10 C 0.72363(14) 0.3300(11) 0.2153(3) 0.0481(10) Uani 1 1 d . . .
C2 C 1.03376(17) 1.4070(13) 0.4706(4) 0.0691(13) Uani 1 1 d . . .
H2 H 1.0625 1.4905 0.5049 0.083 Uiso 1 1 calc R . .
C5 C 0.95241(13) 1.1602(10) 0.3631(4) 0.0507(10) Uani 1 1 d . . .
C9 C 0.76889(12) 0.5319(10) 0.3594(4) 0.0480(9) Uani 1 1 d . . .
H9 H 0.7806 0.5957 0.4317 0.058 Uiso 1 1 calc R . .
C4 C 0.95406(16) 1.1559(13) 0.4823(4) 0.0641(12) Uani 1 1 d . . .
H4 H 0.9275 1.0723 0.5250 0.077 Uiso 1 1 calc R . .
N4 N 0.98848(11) 1.2886(9) 0.2979(3) 0.0609(9) Uani 1 1 d . . .
C7 C 0.83960(13) 0.7413(11) 0.2312(3) 0.0501(9) Uani 1 1 d . . .
C13 C 0.64914(13) 0.0949(12) 0.3593(4) 0.0548(10) Uani 1 1 d . . .
H13 H 0.6239 0.0139 0.4065 0.066 Uiso 1 1 calc R . .
C6 C 0.87164(13) 0.8658(10) 0.3333(3) 0.0501(9) Uani 1 1 d . . .
C3 C 0.99569(18) 1.2778(14) 0.5358(4) 0.0723(14) Uani 1 1 d . . .
H3 H 0.9981 1.2730 0.6156 0.087 Uiso 1 1 calc R . .
C12 C 0.64555(15) 0.0501(12) 0.2395(4) 0.0591(11) Uani 1 1 d . . .
H12 H 0.6179 -0.0591 0.2088 0.071 Uiso 1 1 calc R . .
C1 C 1.02817(15) 1.4091(13) 0.3541(5) 0.0663(12) Uani 1 1 d . . .
H1 H 1.0538 1.5012 0.3104 0.080 Uiso 1 1 calc R . .
H5 H 0.9182(17) 1.040(13) 0.2212(18) 0.079(16) Uiso 1 1 d D . .

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
O2 0.0667(17) 0.103(3) 0.0423(17) -0.0023(18) 0.0052(15) -0.0162(17)
N1 0.0450(15) 0.0513(17) 0.0377(17) 0.0002(15) -0.0015(14) 0.0031(14)
N2 0.0552(17) 0.065(2) 0.0415(16) -0.0083(19) -0.0006(16) -0.0031(15)
N3 0.0534(17) 0.064(2) 0.0435(19) 0.0013(19) 0.0022(15) -0.0061(15)
O1 0.0635(15) 0.092(2) 0.0433(16) -0.0045(18) 0.0047(14) -0.0144(16)
C14 0.060(2) 0.061(2) 0.039(2) 0.001(2) 0.0028(18) 0.001(2)
C11 0.062(2) 0.069(3) 0.045(2) -0.010(2) -0.010(2) -0.008(2)
C8 0.0466(17) 0.051(2) 0.038(2) -0.0019(18) 0.0000(16) 0.0038(16)
C10 0.053(2) 0.056(3) 0.035(2) -0.0006(19) -0.0004(17) 0.0034(19)
C2 0.059(2) 0.068(3) 0.081(4) -0.009(3) -0.013(2) -0.001(2)
C5 0.047(2) 0.053(2) 0.052(2) -0.002(2) 0.0005(19) 0.0026(17)
C9 0.0475(17) 0.056(2) 0.0404(19) -0.005(2) -0.0028(17) 0.0017(16)
C4 0.060(2) 0.080(3) 0.052(3) -0.001(3) 0.002(2) -0.010(2)
N4 0.0546(18) 0.068(2) 0.060(2) 0.000(2) 0.0049(18) -0.0087(17)
C7 0.0488(19) 0.059(2) 0.042(2) -0.0011(19) 0.0042(18) 0.0068(18)
C13 0.0478(19) 0.060(2) 0.057(2) 0.001(2) 0.003(2) -0.0053(18)
C6 0.0481(19) 0.055(2) 0.047(2) 0.002(2) 0.0059(17) 0.0058(18)
C3 0.074(3) 0.085(4) 0.058(3) -0.010(3) -0.009(2) 0.000(3)
C12 0.056(2) 0.062(3) 0.060(3) -0.001(2) -0.010(2) -0.007(2)
C1 0.054(2) 0.065(3) 0.080(3) 0.006(3) 0.005(2) -0.009(2)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C7 1.216(5) . ?
N1 C9 1.366(5) . ?
N1 C14 1.377(5) . ?
N1 C10 1.395(4) . ?
N2 C10 1.320(5) . ?
N2 C8 1.373(5) . ?
N3 C6 1.342(5) . ?
N3 C5 1.413(5) . ?
O1 C6 1.226(5) . ?
C14 C13 1.342(5) . ?
C11 C12 1.349(6) . ?
C11 C10 1.416(5) . ?
C8 C9 1.376(5) . ?
C8 C7 1.455(5) . ?
C2 C1 1.361(7) . ?
C2 C3 1.371(7) . ?
C5 N4 1.330(5) . ?
C5 C4 1.385(6) . ?
C4 C3 1.368(7) . ?
N4 C1 1.339(6) . ?
C7 C6 1.545(5) . ?
C13 C12 1.405(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C14 130.2(3) . . ?
C9 N1 C10 106.7(3) . . ?
C14 N1 C10 123.1(3) . . ?
C10 N2 C8 104.9(3) . . ?
C6 N3 C5 128.9(4) . . ?
C13 C14 N1 118.0(4) . . ?
C12 C11 C10 119.3(4) . . ?
N2 C8 C9 111.4(3) . . ?
N2 C8 C7 119.7(3) . . ?
C9 C8 C7 128.9(4) . . ?
N2 C10 N1 111.4(4) . . ?
N2 C10 C11 131.3(4) . . ?
N1 C10 C11 117.3(4) . . ?
C1 C2 C3 117.9(4) . . ?
N4 C5 C4 123.4(4) . . ?
N4 C5 N3 112.6(4) . . ?
C4 C5 N3 124.0(4) . . ?
N1 C9 C8 105.6(4) . . ?
C3 C4 C5 118.4(4) . . ?
C5 N4 C1 116.0(4) . . ?
O2 C7 C8 123.5(4) . . ?
O2 C7 C6 117.7(3) . . ?
C8 C7 C6 118.8(3) . . ?
C14 C13 C12 121.2(4) . . ?
O1 C6 N3 125.9(4) . . ?
O1 C6 C7 122.3(3) . . ?
N3 C6 C7 111.8(3) . . ?
C4 C3 C2 119.4(5) . . ?
C11 C12 C13 121.1(4) . . ?
N4 C1 C2 124.9(5) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        62.81
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.048