# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_wx

_audit_creation_method           SHELXL-97
_chemical_name_systematic        4p
_chemical_name_common            wx-4
_chemical_melting_point          180-182
_chemical_formula_moiety         C13H12N2O2
_chemical_formula_sum            C13H12N2O2
_chemical_formula_weight         43.03

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   8.7007(12)
_cell_length_b                   15.1805(19)
_cell_length_c                   8.6860(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.082(4)
_cell_angle_gamma                90.00
_cell_volume                     1112.8(2)
_cell_formula_units_Z            22
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             484
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11021
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2529
_reflns_number_gt                1925
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          SQUEEZE

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0612P)²+0.2200P] where P=(Fo²+2Fc²)/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_number_reflns         2529
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1239
_refine_ls_wR_factor_gt          0.1102
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_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 0.08416(12) 1.14152(6) 0.12299(12) 0.0461(3) Uani 1 1 d . . .
O1 O -0.00229(14) 1.12806(6) 0.33951(14) 0.0579(3) Uani 1 1 d . . .
C1 C 0.21495(15) 0.97365(8) 0.15388(16) 0.0375(3) Uani 1 1 d . . .
C2 C 0.22909(15) 1.02643(9) 0.01992(16) 0.0391(3) Uani 1 1 d . . .
N2 N 0.21863(13) 0.87380(7) 0.32496(14) 0.0423(3) Uani 1 1 d . . .
C3 C 0.15979(15) 1.10996(9) 0.01006(16) 0.0400(3) Uani 1 1 d . . .
N1 N 0.26614(13) 0.89155(7) 0.18966(14) 0.0430(3) Uani 1 1 d . . .
C4 C 0.06703(16) 1.09350(9) 0.25140(17) 0.0422(3) Uani 1 1 d . . .
C5 C 0.13642(15) 1.00703(8) 0.26423(16) 0.0386(3) Uani 1 1 d . . .
C6 C 0.30207(18) 1.00123(10) -0.09875(17) 0.0478(4) Uani 1 1 d . . .
H6 H 0.3494 0.9461 -0.0945 0.057 Uiso 1 1 calc R . .
C7 C 0.16097(18) 1.16635(10) -0.11428(17) 0.0488(4) Uani 1 1 d . . .
H7 H 0.1135 1.2215 -0.1194 0.059 Uiso 1 1 calc R . .
C8 C 0.25832(18) 0.78854(9) 0.40367(19) 0.0497(4) Uani 1 1 d . . .
H8A H 0.2225 0.7417 0.3274 0.060 Uiso 1 1 calc R . .
H8B H 0.2028 0.7825 0.4874 0.060 Uiso 1 1 calc R . .
C9 C 0.14171(16) 0.94006(9) 0.37326(17) 0.0428(3) Uani 1 1 d . . .
H9 H 0.1000 0.9411 0.4622 0.051 Uiso 1 1 calc R . .
C10 C 0.43360(19) 0.77880(10) 0.4736(2) 0.0557(4) Uani 1 1 d . . .
H10A H 0.4532 0.7219 0.5254 0.067 Uiso 1 1 calc R . .
H10B H 0.4875 0.7796 0.3881 0.067 Uiso 1 1 calc R . .
C11 C 0.2333(2) 1.13965(11) -0.23014(19) 0.0551(4) Uani 1 1 d . . .
H11 H 0.2346 1.1770 -0.3147 0.066 Uiso 1 1 calc R . .
C12 C 0.3048(2) 1.05748(11) -0.22271(19) 0.0559(4) Uani 1 1 d . . .
H12 H 0.3545 1.0404 -0.3013 0.067 Uiso 1 1 calc R . .
C13 C 0.5033(3) 0.84889(13) 0.5910(2) 0.0783(6) Uani 1 1 d . . .
H13A H 0.4954 0.9048 0.5381 0.117 Uiso 1 1 calc R . .
H13B H 0.6127 0.8357 0.6373 0.117 Uiso 1 1 calc R . .
H13C H 0.4465 0.8511 0.6728 0.117 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
O2 0.0533(6) 0.0359(5) 0.0500(6) 0.0001(4) 0.0140(5) 0.0033(4)
O1 0.0725(8) 0.0436(6) 0.0658(7) -0.0055(5) 0.0326(6) 0.0054(5)
C1 0.0322(6) 0.0355(6) 0.0423(7) -0.0027(5) 0.0041(5) -0.0010(5)
C2 0.0335(6) 0.0397(7) 0.0413(7) -0.0010(6) 0.0039(5) -0.0027(5)
N2 0.0398(6) 0.0384(6) 0.0482(7) 0.0040(5) 0.0093(5) -0.0003(5)
C3 0.0363(7) 0.0391(7) 0.0420(7) -0.0027(6) 0.0046(6) -0.0045(5)
N1 0.0410(6) 0.0400(6) 0.0475(7) 0.0033(5) 0.0097(5) 0.0035(5)
C4 0.0425(7) 0.0373(7) 0.0465(8) -0.0053(6) 0.0100(6) -0.0043(6)
C5 0.0353(7) 0.0358(6) 0.0431(7) -0.0030(5) 0.0068(6) -0.0027(5)
C6 0.0461(8) 0.0492(8) 0.0487(8) -0.0010(6) 0.0127(6) 0.0029(6)
C7 0.0501(8) 0.0419(7) 0.0510(8) 0.0045(6) 0.0058(7) -0.0047(6)
C8 0.0516(9) 0.0363(7) 0.0595(9) 0.0081(6) 0.0103(7) -0.0043(6)
C9 0.0397(7) 0.0421(7) 0.0468(8) -0.0022(6) 0.0107(6) -0.0030(6)
C10 0.0547(9) 0.0437(8) 0.0658(10) 0.0095(7) 0.0089(8) 0.0048(7)
C11 0.0582(9) 0.0567(9) 0.0492(9) 0.0101(7) 0.0106(7) -0.0099(7)
C12 0.0556(9) 0.0665(10) 0.0486(9) -0.0002(7) 0.0188(7) -0.0047(8)
C13 0.0734(12) 0.0633(11) 0.0815(13) 0.0045(10) -0.0135(10) -0.0074(9)

_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 C4 1.3707(17) . ?
O2 C3 1.3924(17) . ?
O1 C4 1.2039(17) . ?
C1 N1 1.3345(17) . ?
C1 C5 1.4003(19) . ?
C1 C2 1.4425(19) . ?
C2 C6 1.389(2) . ?
C2 C3 1.3977(19) . ?
N2 C9 1.3312(18) . ?
N2 N1 1.3642(17) . ?
N2 C8 1.4652(17) . ?
C3 C7 1.380(2) . ?
C4 C5 1.4377(19) . ?
C5 C9 1.3826(19) . ?
C6 C12 1.379(2) . ?
C7 C11 1.372(2) . ?
C8 C10 1.505(2) . ?
C10 C13 1.496(2) . ?
C11 C12 1.388(2) . ?

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
C4 O2 C3 123.63(11) . . ?
N1 C1 C5 111.68(12) . . ?
N1 C1 C2 128.13(12) . . ?
C5 C1 C2 120.18(12) . . ?
C6 C2 C3 118.20(13) . . ?
C6 C2 C1 126.13(13) . . ?
C3 C2 C1 115.66(12) . . ?
C9 N2 N1 113.77(11) . . ?
C9 N2 C8 126.86(13) . . ?
N1 N2 C8 119.34(11) . . ?
C7 C3 O2 115.63(12) . . ?
C7 C3 C2 121.70(13) . . ?
O2 C3 C2 122.67(12) . . ?
C1 N1 N2 103.37(11) . . ?
O1 C4 O2 117.13(13) . . ?
O1 C4 C5 127.92(13) . . ?
O2 C4 C5 114.95(12) . . ?
C9 C5 C1 105.20(12) . . ?
C9 C5 C4 131.90(13) . . ?
C1 C5 C4 122.89(12) . . ?
C12 C6 C2 120.44(14) . . ?
C11 C7 C3 118.88(14) . . ?
N2 C8 C10 112.06(12) . . ?
N2 C9 C5 105.98(12) . . ?
C13 C10 C8 114.07(15) . . ?
C7 C11 C12 120.78(15) . . ?
C6 C12 C11 120.00(15) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.041
_chemical_properties_physical    'Hygroscopic, Heat-sensitive'
_exptl_crystal_preparation       'Magnetic properties'
_database_code_depnum_ccdc_archive 'CCDC 1016208'
