# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_paox
_database_code_depnum_ccdc_archive 'CCDC 1474463'
_audit_update_record             
;
2016-04-15 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;
_chemical_name_common            'Pyrazine-2-Amidoxime '
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H6 N4 O'
_chemical_formula_sum            'C5 H6 N4 O'
_chemical_formula_weight         138.14

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           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   3.78050(15)
_cell_length_b                   10.5723(3)
_cell_length_c                   15.0385(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.249(3)
_cell_angle_gamma                90.00
_cell_volume                     599.41(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    10811
_cell_measurement_theta_min      5.12
_cell_measurement_theta_max      67.33

_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6039
_exptl_absorpt_correction_T_max  0.8928
_exptl_absorpt_process_details   
;
CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd.,
2008)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Ruby CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.4002
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10811
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         5.12
_diffrn_reflns_theta_max         67.33
_reflns_number_total             2162
_reflns_number_gt                1953
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_cell_refinement       
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2003)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0478P)²+0.0058P] 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     SHELXL
_refine_ls_extinction_coef       0.0154(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2162
_refine_ls_number_parameters     200
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0898
_refine_ls_wR_factor_gt          0.0842
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.002
_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
N1A N 0.4670(5) 0.29807(16) 0.36050(11) 0.0390(4) Uani 1 1 d . . .
C2A C 0.5060(5) 0.42282(19) 0.35041(12) 0.0327(5) Uani 1 1 d . . .
C3A C 0.6877(6) 0.4955(2) 0.41624(14) 0.0402(5) Uani 1 1 d . . .
H3A H 0.7187 0.5814 0.4058 0.048 Uiso 1 1 calc R . .
N4A N 0.8182(5) 0.44712(19) 0.49316(12) 0.0462(5) Uani 1 1 d . . .
C5A C 0.7719(6) 0.3230(2) 0.50350(15) 0.0461(6) Uani 1 1 d . . .
H5A H 0.8539 0.2850 0.5569 0.055 Uiso 1 1 calc R . .
C6A C 0.6059(6) 0.2496(2) 0.43727(14) 0.0432(6) Uani 1 1 d . . .
H6A H 0.5899 0.1629 0.4464 0.052 Uiso 1 1 calc R . .
C7A C 0.3364(5) 0.47961(19) 0.26745(12) 0.0321(5) Uani 1 1 d . . .
N8A N 0.2023(6) 0.40015(19) 0.20363(13) 0.0468(5) Uani 1 1 d . . .
H8A H 0.087(7) 0.435(3) 0.1538(18) 0.056 Uiso 1 1 d . . .
H8C H 0.240(7) 0.311(3) 0.2125(17) 0.056 Uiso 1 1 d . . .
N9A N 0.3197(5) 0.60107(16) 0.26423(11) 0.0365(4) Uani 1 1 d . . .
O10A O 0.1468(4) 0.63702(14) 0.18048(9) 0.0429(4) Uani 1 1 d . . .
H10A H 0.050(8) 0.715(3) 0.1911(19) 0.064 Uiso 1 1 d . . .
N1B N 0.2472(5) 1.12499(16) 0.14374(11) 0.0366(4) Uani 1 1 d . . .
C2B C 0.1119(5) 1.00863(18) 0.14535(13) 0.0320(5) Uani 1 1 d . . .
C3B C 0.0941(6) 0.9326(2) 0.06963(13) 0.0408(5) Uani 1 1 d . . .
H3B H -0.0032 0.8521 0.0730 0.049 Uiso 1 1 calc R . .
N4B N 0.2110(6) 0.97056(18) -0.00766(11) 0.0463(5) Uani 1 1 d . . .
C5B C 0.3468(6) 1.0872(2) -0.00826(16) 0.0436(6) Uani 1 1 d . . .
H5B H 0.4321 1.1181 -0.0605 0.052 Uiso 1 1 calc R . .
C6B C 0.3636(6) 1.1623(2) 0.06586(14) 0.0409(5) Uani 1 1 d . . .
H6B H 0.4599 1.2429 0.0621 0.049 Uiso 1 1 calc R . .
C7B C -0.0213(5) 0.96523(18) 0.23064(12) 0.0310(5) Uani 1 1 d . . .
N8B N 0.0159(6) 1.04331(18) 0.30162(13) 0.0436(5) Uani 1 1 d . . .
H8B H -0.020(7) 1.013(3) 0.3552(18) 0.052 Uiso 1 1 d . . .
H8D H 0.149(7) 1.110(3) 0.2959(16) 0.052 Uiso 1 1 d . . .
N9B N -0.1730(5) 0.85612(16) 0.22844(11) 0.0354(4) Uani 1 1 d . . .
O10B O -0.2941(4) 0.82505(14) 0.31289(9) 0.0411(4) Uani 1 1 d . . .
H10B H -0.435(8) 0.747(3) 0.3001(18) 0.062 Uiso 1 1 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
N1A 0.0496(11) 0.0322(10) 0.0351(10) 0.0010(7) 0.0029(8) 0.0018(8)
C2A 0.0355(12) 0.0320(11) 0.0308(10) -0.0007(8) 0.0040(8) 0.0016(9)
C3A 0.0461(13) 0.0343(12) 0.0401(11) -0.0025(9) 0.0019(10) -0.0014(10)
N4A 0.0530(12) 0.0478(12) 0.0370(10) -0.0029(9) -0.0021(8) 0.0005(9)
C5A 0.0487(14) 0.0527(15) 0.0363(11) 0.0042(11) -0.0006(10) 0.0089(12)
C6A 0.0541(15) 0.0356(12) 0.0401(12) 0.0053(10) 0.0031(10) 0.0035(11)
C7A 0.0337(12) 0.0299(11) 0.0331(10) -0.0018(8) 0.0051(8) -0.0002(8)
N8A 0.0712(15) 0.0289(11) 0.0378(11) -0.0032(8) -0.0121(9) 0.0014(9)
N9A 0.0464(11) 0.0291(10) 0.0339(9) 0.0011(7) 0.0014(8) 0.0021(8)
O10A 0.0620(10) 0.0318(9) 0.0344(8) 0.0013(6) -0.0001(7) 0.0086(7)
N1B 0.0415(10) 0.0301(10) 0.0377(9) 0.0020(8) -0.0010(7) -0.0015(8)
C2B 0.0340(11) 0.0261(11) 0.0353(10) -0.0002(8) -0.0013(8) 0.0028(8)
C3B 0.0501(14) 0.0337(12) 0.0379(11) -0.0012(9) -0.0003(9) -0.0022(10)
N4B 0.0579(13) 0.0459(12) 0.0354(10) -0.0030(9) 0.0043(8) -0.0001(10)
C5B 0.0442(14) 0.0502(15) 0.0364(12) 0.0075(10) 0.0027(9) 0.0033(11)
C6B 0.0440(13) 0.0341(13) 0.0445(13) 0.0044(9) 0.0017(10) -0.0026(10)
C7B 0.0317(11) 0.0278(11) 0.0329(10) 0.0013(8) -0.0017(8) 0.0027(8)
N8B 0.0662(14) 0.0303(10) 0.0345(10) -0.0033(8) 0.0054(9) -0.0095(9)
N9B 0.0404(10) 0.0297(9) 0.0360(9) 0.0018(7) 0.0016(7) -0.0007(8)
O10B 0.0508(9) 0.0370(9) 0.0356(8) 0.0019(6) 0.0038(7) -0.0059(8)

_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
N1A C6A 1.335(3) . ?
N1A C2A 1.337(3) . ?
C2A C3A 1.393(3) . ?
C2A C7A 1.486(3) . ?
C3A N4A 1.326(3) . ?
C3A H3A 0.9300 . ?
N4A C5A 1.335(3) . ?
C5A C6A 1.376(3) . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
C7A N9A 1.286(3) . ?
C7A N8A 1.346(3) . ?
N8A H8A 0.92(3) . ?
N8A H8C 0.96(3) . ?
N9A O10A 1.427(2) . ?
O10A H10A 0.92(3) . ?
N1B C2B 1.333(3) . ?
N1B C6B 1.341(3) . ?
C2B C3B 1.391(3) . ?
C2B C7B 1.485(3) . ?
C3B N4B 1.335(3) . ?
C3B H3B 0.9300 . ?
N4B C5B 1.336(3) . ?
C5B C6B 1.366(3) . ?
C5B H5B 0.9300 . ?
C6B H6B 0.9300 . ?
C7B N9B 1.288(3) . ?
C7B N8B 1.348(3) . ?
N8B H8B 0.89(3) . ?
N8B H8D 0.88(3) . ?
N9B O10B 1.420(2) . ?
O10B H10B 0.99(3) . ?

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
C6A N1A C2A 115.92(18) . . ?
N1A C2A C3A 121.07(18) . . ?
N1A C2A C7A 116.70(18) . . ?
C3A C2A C7A 122.20(18) . . ?
N4A C3A C2A 122.6(2) . . ?
N4A C3A H3A 118.7 . . ?
C2A C3A H3A 118.7 . . ?
C3A N4A C5A 115.9(2) . . ?
N4A C5A C6A 121.8(2) . . ?
N4A C5A H5A 119.1 . . ?
C6A C5A H5A 119.1 . . ?
N1A C6A C5A 122.6(2) . . ?
N1A C6A H6A 118.7 . . ?
C5A C6A H6A 118.7 . . ?
N9A C7A N8A 125.5(2) . . ?
N9A C7A C2A 116.86(17) . . ?
N8A C7A C2A 117.55(19) . . ?
C7A N8A H8A 117.4(17) . . ?
C7A N8A H8C 118.0(16) . . ?
H8A N8A H8C 125(2) . . ?
C7A N9A O10A 108.49(17) . . ?
N9A O10A H10A 104.4(18) . . ?
C2B N1B C6B 116.02(17) . . ?
N1B C2B C3B 120.89(19) . . ?
N1B C2B C7B 117.12(17) . . ?
C3B C2B C7B 121.98(18) . . ?
N4B C3B C2B 122.7(2) . . ?
N4B C3B H3B 118.7 . . ?
C2B C3B H3B 118.7 . . ?
C3B N4B C5B 115.80(19) . . ?
N4B C5B C6B 121.7(2) . . ?
N4B C5B H5B 119.1 . . ?
C6B C5B H5B 119.1 . . ?
N1B C6B C5B 122.9(2) . . ?
N1B C6B H6B 118.5 . . ?
C5B C6B H6B 118.5 . . ?
N9B C7B N8B 126.07(18) . . ?
N9B C7B C2B 115.69(17) . . ?
N8B C7B C2B 118.20(18) . . ?
C7B N8B H8B 119.1(18) . . ?
C7B N8B H8D 116.4(16) . . ?
H8B N8B H8D 120(2) . . ?
C7B N9B O10B 110.90(16) . . ?
N9B O10B H10B 102.8(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A N1A C2A C3A 1.2(3) . . . . ?
C6A N1A C2A C7A -176.84(19) . . . . ?
N1A C2A C3A N4A -2.8(3) . . . . ?
C7A C2A C3A N4A 175.1(2) . . . . ?
C2A C3A N4A C5A 1.3(3) . . . . ?
C3A N4A C5A C6A 1.5(3) . . . . ?
C2A N1A C6A C5A 1.6(3) . . . . ?
N4A C5A C6A N1A -3.1(4) . . . . ?
N1A C2A C7A N9A 168.29(19) . . . . ?
C3A C2A C7A N9A -9.7(3) . . . . ?
N1A C2A C7A N8A -9.3(3) . . . . ?
C3A C2A C7A N8A 172.7(2) . . . . ?
N8A C7A N9A O10A -2.1(3) . . . . ?
C2A C7A N9A O10A -179.48(16) . . . . ?
C6B N1B C2B C3B -0.3(3) . . . . ?
C6B N1B C2B C7B -179.59(18) . . . . ?
N1B C2B C3B N4B 0.4(3) . . . . ?
C7B C2B C3B N4B 179.7(2) . . . . ?
C2B C3B N4B C5B -0.2(3) . . . . ?
C3B N4B C5B C6B -0.1(3) . . . . ?
C2B N1B C6B C5B 0.0(3) . . . . ?
N4B C5B C6B N1B 0.1(4) . . . . ?
N1B C2B C7B N9B 175.29(18) . . . . ?
C3B C2B C7B N9B -4.0(3) . . . . ?
N1B C2B C7B N8B -2.7(3) . . . . ?
C3B C2B C7B N8B 178.01(19) . . . . ?
N8B C7B N9B O10B -1.4(3) . . . . ?
C2B C7B N9B O10B -179.15(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        67.33
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.037
