# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_3-methyl-4-nitropyridine-N-oxide_285K

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-methyl-4-nitropyridine-N-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13

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           Orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   21.3830(10)
_cell_length_b                   6.1278(3)
_cell_length_c                   5.1462(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     674.31(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    285(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9637
_exptl_absorpt_correction_T_max  0.9756
_exptl_absorpt_process_details   '(CrysAlis Pro; Oxford Diffraction, 2010)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      285(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  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1895
_diffrn_reflns_av_R_equivalents  0.0121
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         3.46
_diffrn_reflns_theta_max         28.63
_reflns_number_total             952
_reflns_number_gt                830
_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          
; 
 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)+(0.0496P)²+0.0434P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.033(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_number_reflns         952
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0919
_refine_ls_wR_factor_gt          0.0875
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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
N1 N 0.15410(7) 0.0488(2) 0.5071(3) 0.0418(4) Uani 1 1 d . . .
C1 C 0.17916(9) 0.1781(3) 0.3211(4) 0.0401(5) Uani 1 1 d . . .
H1 H 0.2161 0.1338 0.2416 0.048 Uiso 1 1 calc R . .
C2 C 0.15233(8) 0.3738(3) 0.2436(3) 0.0344(4) Uani 1 1 d . . .
C3 C 0.09693(8) 0.4309(3) 0.3696(4) 0.0344(4) Uani 1 1 d . . .
C4 C 0.07181(8) 0.3013(3) 0.5647(4) 0.0394(4) Uani 1 1 d . . .
H2 H 0.0354 0.3440 0.6495 0.047 Uiso 1 1 calc R . .
C5 C 0.10086(9) 0.1106(3) 0.6316(4) 0.0435(5) Uani 1 1 d . . .
H3 H 0.0842 0.0233 0.7621 0.052 Uiso 1 1 calc R . .
O1 O 0.18089(7) -0.1340(2) 0.5679(4) 0.0622(5) Uani 1 1 d . . .
C6 C 0.18670(9) 0.5052(3) 0.0442(4) 0.0467(5) Uani 1 1 d . . .
H4 H 0.2230 0.4262 -0.0124 0.070 Uiso 1 1 calc R . .
H5 H 0.1994 0.6418 0.1188 0.070 Uiso 1 1 calc R . .
H6 H 0.1598 0.5319 -0.1017 0.070 Uiso 1 1 calc R . .
N2 N 0.06263(8) 0.6304(3) 0.3057(3) 0.0441(4) Uani 1 1 d . . .
O2 O 0.07478(8) 0.7233(3) 0.1026(3) 0.0743(6) Uani 1 1 d . . .
O3 O 0.02256(7) 0.6940(2) 0.4562(3) 0.0605(5) Uani 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
N1 0.0423(9) 0.0336(8) 0.0494(9) 0.0087(8) -0.0092(8) -0.0003(6)
C1 0.0345(9) 0.0401(10) 0.0457(10) 0.0014(9) 0.0000(9) 0.0013(8)
C2 0.0337(9) 0.0358(9) 0.0338(9) 0.0023(8) -0.0035(7) -0.0033(7)
C3 0.0328(9) 0.0328(8) 0.0375(9) 0.0015(8) -0.0064(8) -0.0014(7)
C4 0.0335(9) 0.0419(9) 0.0427(10) 0.0027(9) 0.0013(9) -0.0034(8)
C5 0.0423(10) 0.0444(10) 0.0439(11) 0.0108(10) 0.0001(9) -0.0093(9)
O1 0.0620(9) 0.0415(7) 0.0831(12) 0.0202(9) -0.0079(9) 0.0124(7)
C6 0.0427(10) 0.0527(11) 0.0448(10) 0.0098(11) 0.0061(9) -0.0022(9)
N2 0.0388(9) 0.0405(8) 0.0531(10) 0.0048(8) -0.0059(8) 0.0034(7)
O2 0.0681(11) 0.0776(12) 0.0773(11) 0.0434(10) 0.0082(10) 0.0237(9)
O3 0.0569(9) 0.0551(9) 0.0695(10) -0.0049(10) 0.0077(9) 0.0188(7)

_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
N1 O1 1.2966(19) . ?
N1 C1 1.353(3) . ?
N1 C5 1.360(3) . ?
C1 C2 1.388(3) . ?
C2 C3 1.395(2) . ?
C2 C6 1.497(2) . ?
C3 C4 1.388(2) . ?
C3 N2 1.463(2) . ?
C4 C5 1.367(3) . ?
N2 O2 1.218(2) . ?
N2 O3 1.219(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
O1 N1 C1 120.11(18) . . ?
O1 N1 C5 119.80(17) . . ?
C1 N1 C5 120.09(15) . . ?
N1 C1 C2 123.07(18) . . ?
C1 C2 C3 115.73(17) . . ?
C1 C2 C6 117.32(17) . . ?
C3 C2 C6 126.89(17) . . ?
C4 C3 C2 121.42(16) . . ?
C4 C3 N2 116.51(17) . . ?
C2 C3 N2 122.07(16) . . ?
C5 C4 C3 119.68(18) . . ?
N1 C5 C4 119.98(17) . . ?
O2 N2 O3 123.07(18) . . ?
O2 N2 C3 118.43(18) . . ?
O3 N2 C3 118.48(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
O1 N1 C1 C2 178.86(17) . . . . ?
C5 N1 C1 C2 -1.4(3) . . . . ?
N1 C1 C2 C3 -0.2(3) . . . . ?
N1 C1 C2 C6 177.28(17) . . . . ?
C1 C2 C3 C4 1.7(3) . . . . ?
C6 C2 C3 C4 -175.47(18) . . . . ?
C1 C2 C3 N2 -178.93(16) . . . . ?
C6 C2 C3 N2 3.9(3) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
N2 C3 C4 C5 178.95(16) . . . . ?
O1 N1 C5 C4 -178.78(17) . . . . ?
C1 N1 C5 C4 1.5(3) . . . . ?
C3 C4 C5 N1 0.0(3) . . . . ?
C4 C3 N2 O2 -164.36(18) . . . . ?
C2 C3 N2 O2 16.2(3) . . . . ?
C4 C3 N2 O3 14.5(2) . . . . ?
C2 C3 N2 O3 -164.94(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.914
_diffrn_reflns_theta_full        28.63
_diffrn_measured_fraction_theta_full 0.914
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.032
_database_code_depnum_ccdc_archive 'CCDC 979868'
#######################################################################
#
#                 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_3-methyl-4-nitropyridine-N-oxide_300K

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-methyl-4-nitropyridine-N-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13

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           Orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   21.4311(11)
_cell_length_b                   6.1298(3)
_cell_length_c                   5.1489(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     676.40(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9638
_exptl_absorpt_correction_T_max  0.9757
_exptl_absorpt_process_details   '(CrysAlis Pro; Oxford Diffraction, 2010)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      300(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  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1902
_diffrn_reflns_av_R_equivalents  0.0129
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         3.46
_diffrn_reflns_theta_max         28.60
_reflns_number_total             955
_reflns_number_gt                833
_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          
; 
 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)+(0.0417P)²+0.0763P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.034(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(6)
_refine_ls_number_reflns         955
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0895
_refine_ls_wR_factor_gt          0.0847
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_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
N1 N 0.15410(7) 0.0483(2) 0.5086(3) 0.0444(4) Uani 1 1 d . . .
C1 C 0.17919(9) 0.1780(3) 0.3226(4) 0.0419(5) Uani 1 1 d . . .
H1 H 0.2161 0.1340 0.2433 0.050 Uiso 1 1 calc R . .
C2 C 0.15235(8) 0.3727(3) 0.2453(3) 0.0364(4) Uani 1 1 d . . .
C3 C 0.09703(8) 0.4301(3) 0.3704(4) 0.0367(4) Uani 1 1 d . . .
C4 C 0.07185(9) 0.3001(3) 0.5648(4) 0.0424(5) Uani 1 1 d . . .
H2 H 0.0354 0.3423 0.6488 0.051 Uiso 1 1 calc R . .
C5 C 0.10086(9) 0.1100(3) 0.6322(4) 0.0461(5) Uani 1 1 d . . .
H3 H 0.0842 0.0227 0.7626 0.055 Uiso 1 1 calc R . .
O1 O 0.18094(8) -0.1341(2) 0.5694(4) 0.0672(5) Uani 1 1 d . . .
C6 C 0.18668(10) 0.5045(4) 0.0450(4) 0.0494(5) Uani 1 1 d . . .
H4 H 0.2229 0.4256 -0.0115 0.074 Uiso 1 1 calc R . .
H5 H 0.1993 0.6412 0.1193 0.074 Uiso 1 1 calc R . .
H6 H 0.1598 0.5309 -0.1008 0.074 Uiso 1 1 calc R . .
N2 N 0.06259(8) 0.6292(3) 0.3061(4) 0.0468(4) Uani 1 1 d . . .
O2 O 0.07476(9) 0.7221(3) 0.1031(4) 0.0793(6) Uani 1 1 d . . .
O3 O 0.02250(8) 0.6923(3) 0.4560(4) 0.0642(5) Uani 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
N1 0.0427(9) 0.0363(8) 0.0541(10) 0.0087(8) -0.0090(8) 0.0008(6)
C1 0.0361(9) 0.0409(10) 0.0485(11) 0.0019(10) 0.0009(9) 0.0006(8)
C2 0.0357(9) 0.0378(9) 0.0356(9) 0.0023(8) -0.0038(8) -0.0036(8)
C3 0.0343(9) 0.0355(9) 0.0404(10) 0.0017(8) -0.0059(8) -0.0016(7)
C4 0.0369(9) 0.0456(10) 0.0448(10) 0.0013(10) 0.0021(9) -0.0041(8)
C5 0.0453(10) 0.0465(11) 0.0467(11) 0.0102(10) 0.0000(9) -0.0093(9)
O1 0.0664(10) 0.0457(8) 0.0894(13) 0.0217(9) -0.0083(10) 0.0127(8)
C6 0.0469(10) 0.0551(11) 0.0462(11) 0.0126(11) 0.0073(10) -0.0032(10)
N2 0.0427(9) 0.0422(9) 0.0556(10) 0.0047(9) -0.0054(8) 0.0031(8)
O2 0.0732(11) 0.0827(12) 0.0819(12) 0.0460(11) 0.0079(10) 0.0252(10)
O3 0.0606(9) 0.0584(9) 0.0737(11) -0.0039(10) 0.0087(9) 0.0206(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
N1 O1 1.296(2) . ?
N1 C1 1.356(3) . ?
N1 C5 1.360(3) . ?
C1 C2 1.384(3) . ?
C2 C3 1.394(3) . ?
C2 C6 1.502(3) . ?
C3 C4 1.389(3) . ?
C3 N2 1.464(2) . ?
C4 C5 1.365(3) . ?
N2 O3 1.218(2) . ?
N2 O2 1.218(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
O1 N1 C1 120.04(18) . . ?
O1 N1 C5 119.94(18) . . ?
C1 N1 C5 120.02(16) . . ?
N1 C1 C2 122.96(18) . . ?
C1 C2 C3 116.00(17) . . ?
C1 C2 C6 117.24(18) . . ?
C3 C2 C6 126.71(17) . . ?
C4 C3 C2 121.23(17) . . ?
C4 C3 N2 116.46(17) . . ?
C2 C3 N2 122.31(16) . . ?
C5 C4 C3 119.74(19) . . ?
N1 C5 C4 120.01(18) . . ?
O3 N2 O2 123.13(19) . . ?
O3 N2 C3 118.47(17) . . ?
O2 N2 C3 118.39(19) . . ?

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
O1 N1 C1 C2 178.85(18) . . . . ?
C5 N1 C1 C2 -1.4(3) . . . . ?
N1 C1 C2 C3 -0.1(3) . . . . ?
N1 C1 C2 C6 177.47(17) . . . . ?
C1 C2 C3 C4 1.5(3) . . . . ?
C6 C2 C3 C4 -175.85(19) . . . . ?
C1 C2 C3 N2 -178.81(17) . . . . ?
C6 C2 C3 N2 3.9(3) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
N2 C3 C4 C5 178.91(16) . . . . ?
O1 N1 C5 C4 -178.71(18) . . . . ?
C1 N1 C5 C4 1.5(3) . . . . ?
C3 C4 C5 N1 -0.2(3) . . . . ?
C4 C3 N2 O3 14.7(3) . . . . ?
C2 C3 N2 O3 -165.04(18) . . . . ?
C4 C3 N2 O2 -164.22(19) . . . . ?
C2 C3 N2 O2 16.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.916
_diffrn_reflns_theta_full        28.60
_diffrn_measured_fraction_theta_full 0.916
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.031
_database_code_depnum_ccdc_archive 'CCDC 979869'
#######################################################################
#
#                 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_3-methyl-4-nitropyridine-N-oxide_0.1MPa

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-methyl-4-nitropyridine-N-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13

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           Orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   21.4235(4)
_cell_length_b                   6.12750(10)
_cell_length_c                   5.14870(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     675.88(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9521
_exptl_absorpt_correction_T_max  0.9638
_exptl_absorpt_process_details   '(CrysAlis Pro; Oxford Diffraction, 2010)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17434
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0110
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.46
_diffrn_reflns_theta_max         28.33
_reflns_number_total             985
_reflns_number_gt                878
_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          
; 
 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)+(0.0346P)²+0.0641P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.035(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_number_reflns         985
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0825
_refine_ls_wR_factor_gt          0.0804
_refine_ls_goodness_of_fit_ref   1.244
_refine_ls_restrained_S_all      1.244
_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
N1 N 0.15407(6) 0.0486(2) 0.5085(3) 0.0439(4) Uani 1 1 d . . .
C1 C 0.17911(8) 0.1781(3) 0.3221(4) 0.0409(4) Uani 1 1 d . . .
H1 H 0.2160 0.1339 0.2427 0.049 Uiso 1 1 calc R . .
C2 C 0.15237(7) 0.3730(3) 0.2447(3) 0.0359(4) Uani 1 1 d . . .
C3 C 0.09685(7) 0.4300(3) 0.3703(3) 0.0357(4) Uani 1 1 d . . .
C4 C 0.07187(7) 0.3004(3) 0.5647(3) 0.0411(4) Uani 1 1 d . . .
H2 H 0.0355 0.3430 0.6492 0.049 Uiso 1 1 calc R . .
C5 C 0.10076(8) 0.1099(3) 0.6322(4) 0.0452(5) Uani 1 1 d . . .
H3 H 0.0840 0.0224 0.7624 0.054 Uiso 1 1 calc R . .
O1 O 0.18097(6) -0.1343(2) 0.5693(3) 0.0652(5) Uani 1 1 d . . .
C6 C 0.18663(8) 0.5047(3) 0.0450(4) 0.0490(5) Uani 1 1 d . . .
H4 H 0.2232 0.4268 -0.0097 0.073 Uiso 1 1 calc R . .
H5 H 0.1987 0.6424 0.1186 0.073 Uiso 1 1 calc R . .
H6 H 0.1600 0.5293 -0.1020 0.073 Uiso 1 1 calc R . .
N2 N 0.06266(7) 0.6293(3) 0.3058(3) 0.0460(4) Uani 1 1 d . . .
O2 O 0.07475(7) 0.7222(3) 0.1028(3) 0.0777(6) Uani 1 1 d . . .
O3 O 0.02246(6) 0.6926(2) 0.4560(3) 0.0638(5) Uani 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
N1 0.0427(7) 0.0364(8) 0.0525(9) 0.0087(8) -0.0092(7) -0.0004(6)
C1 0.0355(8) 0.0401(9) 0.0471(10) 0.0021(9) 0.0003(8) 0.0013(7)
C2 0.0351(8) 0.0388(9) 0.0339(9) 0.0015(8) -0.0034(7) -0.0045(7)
C3 0.0334(8) 0.0342(8) 0.0396(9) 0.0023(8) -0.0058(7) -0.0011(7)
C4 0.0347(8) 0.0449(9) 0.0437(10) 0.0019(9) 0.0029(8) -0.0036(7)
C5 0.0434(9) 0.0458(10) 0.0462(11) 0.0104(9) -0.0001(8) -0.0088(8)
O1 0.0645(8) 0.0443(8) 0.0869(12) 0.0214(9) -0.0083(9) 0.0132(7)
C6 0.0455(9) 0.0557(11) 0.0456(10) 0.0106(11) 0.0064(9) -0.0019(9)
N2 0.0403(7) 0.0422(8) 0.0555(10) 0.0048(8) -0.0044(7) 0.0033(7)
O2 0.0717(9) 0.0814(12) 0.0798(11) 0.0456(10) 0.0083(9) 0.0254(9)
O3 0.0600(8) 0.0588(9) 0.0727(10) -0.0046(9) 0.0084(8) 0.0201(7)

_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
N1 O1 1.2983(18) . ?
N1 C1 1.356(2) . ?
N1 C5 1.361(2) . ?
C1 C2 1.383(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.398(2) . ?
C2 C6 1.499(2) . ?
C3 C4 1.386(2) . ?
C3 N2 1.462(2) . ?
C4 C5 1.366(2) . ?
C4 H2 0.9300 . ?
C5 H3 0.9300 . ?
C6 H4 0.9600 . ?
C6 H5 0.9600 . ?
C6 H6 0.9600 . ?
N2 O2 1.218(2) . ?
N2 O3 1.220(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
O1 N1 C1 120.03(16) . . ?
O1 N1 C5 119.86(16) . . ?
C1 N1 C5 120.11(15) . . ?
N1 C1 C2 123.07(16) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C1 C2 C3 115.76(16) . . ?
C1 C2 C6 117.36(16) . . ?
C3 C2 C6 126.83(16) . . ?
C4 C3 C2 121.31(16) . . ?
C4 C3 N2 116.69(15) . . ?
C2 C3 N2 122.00(15) . . ?
C5 C4 C3 119.91(16) . . ?
C5 C4 H2 120.0 . . ?
C3 C4 H2 120.0 . . ?
N1 C5 C4 119.80(17) . . ?
N1 C5 H3 120.1 . . ?
C4 C5 H3 120.1 . . ?
C2 C6 H4 109.5 . . ?
C2 C6 H5 109.5 . . ?
H4 C6 H5 109.5 . . ?
C2 C6 H6 109.5 . . ?
H4 C6 H6 109.5 . . ?
H5 C6 H6 109.5 . . ?
O2 N2 O3 123.03(17) . . ?
O2 N2 C3 118.57(17) . . ?
O3 N2 C3 118.38(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
O1 N1 C1 C2 178.88(16) . . . . ?
C5 N1 C1 C2 -1.2(3) . . . . ?
N1 C1 C2 C3 -0.3(3) . . . . ?
N1 C1 C2 C6 177.31(16) . . . . ?
C1 C2 C3 C4 1.8(2) . . . . ?
C6 C2 C3 C4 -175.62(17) . . . . ?
C1 C2 C3 N2 -178.92(15) . . . . ?
C6 C2 C3 N2 3.7(3) . . . . ?
C2 C3 C4 C5 -1.7(3) . . . . ?
N2 C3 C4 C5 178.93(15) . . . . ?
O1 N1 C5 C4 -178.80(16) . . . . ?
C1 N1 C5 C4 1.3(3) . . . . ?
C3 C4 C5 N1 0.2(3) . . . . ?
C4 C3 N2 O2 -164.29(17) . . . . ?
C2 C3 N2 O2 16.4(2) . . . . ?
C4 C3 N2 O3 14.4(2) . . . . ?
C2 C3 N2 O3 -164.99(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.967
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.030
_database_code_depnum_ccdc_archive 'CCDC 979870'
#######################################################################
#
#                 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_3-methyl-4-nitropyridine_N-oxide_0.07GPa

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-methyl-4-nitropyridineN-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13

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           Orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   21.363(5)
_cell_length_b                   6.141(5)
_cell_length_c                   5.1404(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     674.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       70000
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.6066
_exptl_absorpt_correction_T_max  0.9361
_exptl_absorpt_process_details   
;   
Katrusiak, A. (2003). REDSHABS - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Poznań.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467
;
_exptl_special_details           
; 
 Data were collected at room temperature and pressure of 0.07(3) GPa
 (70000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique.
 Pressure was determined by monitoring the shift of the ruby
 R1-fluorescence line.
;

_diffrn_ambient_temperature      296(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  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       
;HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2608
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.82
_diffrn_reflns_theta_max         27.45
_reflns_number_total             364
_reflns_number_gt                291
_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          
; 
 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)+(0.0532P)²+0.3254P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_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   6(7)
_refine_ls_number_reflns         364
_refine_ls_number_parameters     100
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1280
_refine_ls_wR_factor_gt          0.1136
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_restrained_S_all      1.097
_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
N1 N 0.1547(2) 0.040(2) 0.5075(11) 0.052(4) Uani 1 1 d DU . .
C1 C 0.1786(2) 0.179(2) 0.3224(12) 0.043(4) Uani 1 1 d DU . .
H1 H 0.2159 0.1379 0.2431 0.052 Uiso 1 1 calc R . .
C2 C 0.1523(2) 0.374(2) 0.2433(9) 0.038(4) Uani 1 1 d DU . .
C3 C 0.0969(2) 0.432(2) 0.3708(10) 0.042(4) Uani 1 1 d DU . .
C4 C 0.0722(3) 0.299(2) 0.5620(11) 0.045(4) Uani 1 1 d DU . .
H2 H 0.0352 0.3401 0.6441 0.054 Uiso 1 1 calc R . .
C5 C 0.1002(3) 0.109(2) 0.6340(11) 0.047(5) Uani 1 1 d DU . .
H3 H 0.0831 0.0246 0.7668 0.056 Uiso 1 1 calc R . .
O1 O 0.1808(2) -0.142(2) 0.5698(11) 0.085(5) Uani 1 1 d DU . .
C6 C 0.1867(2) 0.507(2) 0.0451(10) 0.052(4) Uani 1 1 d DU . .
H4 H 0.2230 0.4293 -0.0126 0.077 Uiso 1 1 calc R . .
H5 H 0.1993 0.6431 0.1217 0.077 Uiso 1 1 calc R . .
H6 H 0.1597 0.5353 -0.1005 0.077 Uiso 1 1 calc R . .
N2 N 0.0628(2) 0.631(2) 0.3048(10) 0.052(4) Uani 1 1 d DU . .
O2 O 0.07460(19) 0.718(2) 0.1022(9) 0.076(4) Uani 1 1 d U . .
O3 O 0.02208(18) 0.688(2) 0.4565(9) 0.072(4) Uani 1 1 d U . .

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
N1 0.045(3) 0.050(13) 0.060(3) 0.009(6) -0.009(3) -0.002(5)
C1 0.035(3) 0.038(13) 0.055(3) 0.003(7) -0.001(3) -0.007(6)
C2 0.044(3) 0.039(13) 0.033(3) -0.001(6) -0.006(2) -0.003(6)
C3 0.036(2) 0.040(13) 0.049(3) 0.019(6) -0.004(2) 0.010(6)
C4 0.042(3) 0.040(13) 0.052(3) 0.003(7) 0.004(3) -0.014(6)
C5 0.050(3) 0.046(13) 0.044(3) -0.002(7) 0.003(2) -0.001(6)
O1 0.073(3) 0.084(13) 0.096(4) 0.018(7) -0.011(3) -0.001(6)
C6 0.061(3) 0.049(13) 0.045(3) -0.003(7) 0.002(2) -0.004(6)
N2 0.042(2) 0.055(13) 0.059(3) 0.003(7) -0.005(2) -0.002(5)
O2 0.082(3) 0.070(12) 0.077(3) 0.027(6) 0.009(2) 0.014(5)
O3 0.063(2) 0.068(12) 0.084(3) 0.000(6) 0.013(2) 0.019(5)

_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
N1 O1 1.293(7) . ?
N1 C1 1.376(13) . ?
N1 C5 1.398(9) . ?
C1 C2 1.384(7) . ?
C2 C3 1.399(9) . ?
C2 C6 1.499(7) . ?
C3 C4 1.384(7) . ?
C3 N2 1.463(7) . ?
C4 C5 1.362(7) . ?
N2 O2 1.199(9) . ?
N2 O3 1.220(7) . ?

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
O1 N1 C1 123.2(7) . . ?
O1 N1 C5 120.3(8) . . ?
C1 N1 C5 116.4(10) . . ?
N1 C1 C2 126.1(6) . . ?
C1 C2 C3 115.1(7) . . ?
C1 C2 C6 118.3(7) . . ?
C3 C2 C6 126.5(9) . . ?
C4 C3 C2 120.4(9) . . ?
C4 C3 N2 117.9(6) . . ?
C2 C3 N2 121.6(7) . . ?
C5 C4 C3 122.1(7) . . ?
C4 C5 N1 119.8(8) . . ?
O2 N2 O3 125.3(11) . . ?
O2 N2 C3 118.1(7) . . ?
O3 N2 C3 116.5(8) . . ?

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
O1 N1 C1 C2 178.6(6) . . . . ?
C5 N1 C1 C2 -2.9(9) . . . . ?
N1 C1 C2 C3 1.1(8) . . . . ?
N1 C1 C2 C6 177.8(6) . . . . ?
C1 C2 C3 C4 0.3(8) . . . . ?
C6 C2 C3 C4 -175.9(6) . . . . ?
C1 C2 C3 N2 -178.6(5) . . . . ?
C6 C2 C3 N2 5.1(9) . . . . ?
C2 C3 C4 C5 0.1(10) . . . . ?
N2 C3 C4 C5 179.1(5) . . . . ?
C3 C4 C5 N1 -1.9(10) . . . . ?
O1 N1 C5 C4 -178.3(6) . . . . ?
C1 N1 C5 C4 3.1(9) . . . . ?
C4 C3 N2 O2 -162.1(8) . . . . ?
C2 C3 N2 O2 16.9(9) . . . . ?
C4 C3 N2 O3 14.2(9) . . . . ?
C2 C3 N2 O3 -166.8(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.272
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.272
_refine_diff_density_max         0.097
_refine_diff_density_min         -0.113
_refine_diff_density_rms         0.031
_database_code_depnum_ccdc_archive 'CCDC 979871'
#######################################################################
#
#                 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_3-methyl-4-nitropyridine_N-oxide_0.12GPa

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-methyl-4-nitropyridineN-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13

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           Orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   21.325(5)
_cell_length_b                   6.152(6)
_cell_length_c                   5.1306(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     673.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       120000
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.5385
_exptl_absorpt_correction_T_max  0.9816
_exptl_absorpt_process_details   
;   
Katrusiak, A. (2003). REDSHABS - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Poznań.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467
;
_exptl_special_details           
; 
 Data were collected at room temperature and pressure of 0.12(3) GPa
 (120000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique.
 Pressure was determined by monitoring the shift of the ruby
 R1-fluorescence line.
;

_diffrn_ambient_temperature      296(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  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       
;HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2622
_diffrn_reflns_av_R_equivalents  0.0746
_diffrn_reflns_av_sigmaI/netI    0.0529
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.82
_diffrn_reflns_theta_max         27.98
_reflns_number_total             359
_reflns_number_gt                298
_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          
; 
 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)+(0.0000P)²+0.2731P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.078(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   4(7)
_refine_ls_number_reflns         359
_refine_ls_number_parameters     101
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_ref         0.0846
_refine_ls_wR_factor_gt          0.0780
_refine_ls_goodness_of_fit_ref   1.308
_refine_ls_restrained_S_all      1.231
_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
N1 N 0.1548(2) 0.050(2) 0.5062(11) 0.047(5) Uani 1 1 d DU . .
C1 C 0.1783(2) 0.186(3) 0.3171(12) 0.040(4) Uani 1 1 d DU . .
H1 H 0.2150 0.1433 0.2342 0.048 Uiso 1 1 calc R . .
C2 C 0.1516(2) 0.381(2) 0.2396(9) 0.037(4) Uani 1 1 d DU . .
C3 C 0.0968(2) 0.4377(19) 0.3711(10) 0.033(4) Uani 1 1 d DU . .
C4 C 0.0730(3) 0.301(2) 0.5606(12) 0.046(5) Uani 1 1 d DU . .
H2 H 0.0363 0.3436 0.6449 0.055 Uiso 1 1 calc R . .
C5 C 0.0994(3) 0.109(2) 0.6324(12) 0.054(5) Uani 1 1 d DU . .
H3 H 0.0814 0.0212 0.7596 0.065 Uiso 1 1 calc R . .
O1 O 0.1804(2) -0.134(2) 0.5687(11) 0.084(5) Uani 1 1 d DU . .
C6 C 0.1873(2) 0.512(3) 0.0419(10) 0.055(5) Uani 1 1 d DU . .
H4 H 0.2235 0.4313 -0.0135 0.083 Uiso 1 1 calc R . .
H5 H 0.2004 0.6467 0.1185 0.083 Uiso 1 1 calc R . .
H6 H 0.1609 0.5406 -0.1056 0.083 Uiso 1 1 calc R . .
N2 N 0.0629(2) 0.636(2) 0.3054(11) 0.047(4) Uani 1 1 d DU . .
O2 O 0.07465(19) 0.718(3) 0.1012(10) 0.077(4) Uani 1 1 d U . .
O3 O 0.02229(15) 0.695(2) 0.4543(8) 0.064(4) Uani 1 1 d U . .

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
N1 0.039(3) 0.043(13) 0.060(3) 0.005(6) -0.012(3) -0.006(5)
C1 0.030(2) 0.044(13) 0.047(3) 0.015(7) 0.005(3) -0.008(6)
C2 0.043(3) 0.032(13) 0.036(3) 0.003(7) -0.008(2) -0.012(6)
C3 0.027(2) 0.028(13) 0.045(3) 0.009(6) -0.006(2) 0.007(6)
C4 0.048(3) 0.046(13) 0.044(4) 0.017(7) 0.008(3) -0.003(7)
C5 0.058(3) 0.054(13) 0.050(4) 0.006(7) 0.000(3) 0.000(7)
O1 0.066(3) 0.086(13) 0.101(4) 0.000(8) -0.007(3) 0.005(6)
C6 0.056(3) 0.058(13) 0.052(3) 0.001(7) 0.004(2) -0.011(6)
N2 0.038(2) 0.052(13) 0.051(3) 0.014(6) -0.003(2) -0.001(5)
O2 0.075(2) 0.074(12) 0.083(3) 0.025(6) 0.010(2) 0.007(5)
O3 0.056(2) 0.059(12) 0.079(3) 0.004(6) 0.0147(19) 0.019(5)

_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
N1 O1 1.298(7) . ?
N1 C1 1.375(13) . ?
N1 C5 1.395(10) . ?
C1 C2 1.389(7) . ?
C2 C3 1.393(9) . ?
C2 C6 1.501(7) . ?
C3 C4 1.382(7) . ?
C3 N2 1.456(7) . ?
C4 C5 1.360(7) . ?
N2 O2 1.190(9) . ?
N2 O3 1.210(7) . ?

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
O1 N1 C1 123.5(8) . . ?
O1 N1 C5 118.0(8) . . ?
C1 N1 C5 118.5(10) . . ?
N1 C1 C2 125.4(7) . . ?
C1 C2 C3 114.9(7) . . ?
C1 C2 C6 116.6(7) . . ?
C3 C2 C6 128.4(9) . . ?
C4 C3 C2 119.9(9) . . ?
C4 C3 N2 119.2(7) . . ?
C2 C3 N2 120.8(7) . . ?
C5 C4 C3 124.5(8) . . ?
C4 C5 N1 116.8(9) . . ?
O2 N2 O3 125.3(11) . . ?
O2 N2 C3 117.1(8) . . ?
O3 N2 C3 117.4(7) . . ?

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
O1 N1 C1 C2 178.3(6) . . . . ?
C5 N1 C1 C2 0.5(9) . . . . ?
N1 C1 C2 C3 0.3(8) . . . . ?
N1 C1 C2 C6 176.0(6) . . . . ?
C1 C2 C3 C4 -0.5(8) . . . . ?
C6 C2 C3 C4 -175.6(6) . . . . ?
C1 C2 C3 N2 -178.4(5) . . . . ?
C6 C2 C3 N2 6.6(9) . . . . ?
C2 C3 C4 C5 -0.1(10) . . . . ?
N2 C3 C4 C5 177.8(6) . . . . ?
C3 C4 C5 N1 0.9(10) . . . . ?
O1 N1 C5 C4 -179.0(6) . . . . ?
C1 N1 C5 C4 -1.0(9) . . . . ?
C4 C3 N2 O2 -160.7(8) . . . . ?
C2 C3 N2 O2 17.2(9) . . . . ?
C4 C3 N2 O3 14.6(8) . . . . ?
C2 C3 N2 O3 -167.5(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.257
_diffrn_reflns_theta_full        27.98
_diffrn_measured_fraction_theta_full 0.257
_refine_diff_density_max         0.064
_refine_diff_density_min         -0.057
_refine_diff_density_rms         0.018
_database_code_depnum_ccdc_archive 'CCDC 979872'
#######################################################################
#
#                 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_3-methyl-4-nitropyridine_N-oxide_0.21GPa

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-methyl-4-nitropyridineN-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13

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           Orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   21.267(5)
_cell_length_b                   6.133(5)
_cell_length_c                   5.1284(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     668.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       210000
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.5274
_exptl_absorpt_correction_T_max  0.9801
_exptl_absorpt_process_details   
; 
Katrusiak, A. (2003). REDSHABS - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Poznań.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467
;
_exptl_special_details           
; 
 Data were collected at room temperature and pressure of 0.21(3) GPa
 (210000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique.
 Pressure was determined by monitoring the shift of the ruby
 R1-fluorescence line.
;

_diffrn_ambient_temperature      296(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  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       
;HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2577
_diffrn_reflns_av_R_equivalents  0.1065
_diffrn_reflns_av_sigmaI/netI    0.0499
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         5.52
_diffrn_reflns_theta_max         27.09
_reflns_number_total             364
_reflns_number_gt                321
_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          
; 
 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)+(0.0398P)²+0.3018P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_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   2(6)
_refine_ls_number_reflns         364
_refine_ls_number_parameters     100
_refine_ls_number_restraints     74
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.1061
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_restrained_S_all      1.095
_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
N1 N 0.15453(19) 0.044(3) 0.5074(10) 0.049(4) Uani 1 1 d DU . .
C1 C 0.1791(2) 0.184(3) 0.3168(10) 0.042(4) Uani 1 1 d DU . .
H1 H 0.2164 0.1431 0.2361 0.050 Uiso 1 1 calc R . .
C2 C 0.15251(19) 0.374(2) 0.2414(8) 0.037(4) Uani 1 1 d DU . .
C3 C 0.0965(2) 0.4317(18) 0.3673(8) 0.034(4) Uani 1 1 d DU . .
C4 C 0.0711(2) 0.3029(19) 0.5609(9) 0.046(4) Uani 1 1 d DU . .
H2 H 0.0343 0.3463 0.6441 0.055 Uiso 1 1 calc R . .
C5 C 0.0993(2) 0.113(2) 0.6313(10) 0.047(4) Uani 1 1 d DU . .
H3 H 0.0819 0.0286 0.7631 0.057 Uiso 1 1 calc R . .
O1 O 0.1810(2) -0.142(2) 0.5654(9) 0.082(4) Uani 1 1 d U . .
C6 C 0.1870(2) 0.506(2) 0.0398(8) 0.052(4) Uani 1 1 d DU . .
H4 H 0.2234 0.4267 -0.0175 0.079 Uiso 1 1 calc R . .
H5 H 0.1998 0.6425 0.1141 0.079 Uiso 1 1 calc R . .
H6 H 0.1598 0.5322 -0.1062 0.079 Uiso 1 1 calc R . .
N2 N 0.06268(17) 0.6313(19) 0.3018(9) 0.050(4) Uani 1 1 d DU . .
O2 O 0.07489(16) 0.722(3) 0.0985(7) 0.075(4) Uani 1 1 d U . .
O3 O 0.02151(16) 0.6900(19) 0.4536(7) 0.071(4) Uani 1 1 d U . .

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
N1 0.044(2) 0.045(13) 0.057(2) 0.000(5) -0.005(2) -0.003(5)
C1 0.038(2) 0.038(13) 0.049(3) 0.005(6) -0.004(2) -0.008(5)
C2 0.034(2) 0.041(13) 0.036(2) -0.002(5) -0.0051(17) -0.010(5)
C3 0.0357(19) 0.024(13) 0.040(2) 0.006(5) -0.0014(18) 0.003(5)
C4 0.038(2) 0.046(13) 0.053(3) 0.007(6) 0.008(2) -0.004(5)
C5 0.046(2) 0.048(13) 0.048(3) -0.003(6) 0.000(2) 0.001(6)
O1 0.072(3) 0.081(13) 0.093(3) 0.013(7) -0.009(2) 0.008(6)
C6 0.055(2) 0.057(13) 0.045(2) 0.003(6) 0.0036(18) -0.012(6)
N2 0.0384(18) 0.053(13) 0.060(2) 0.004(6) -0.0001(19) 0.005(4)
O2 0.074(2) 0.076(12) 0.075(2) 0.038(6) 0.0117(18) 0.009(5)
O3 0.0629(18) 0.071(12) 0.079(2) 0.005(6) 0.0093(17) 0.026(5)

_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
N1 O1 1.307(19) . ?
N1 C1 1.402(16) . ?
N1 C5 1.401(9) . ?
C1 C2 1.353(17) . ?
C2 C3 1.400(8) . ?
C2 C6 1.502(7) . ?
C3 C4 1.379(6) . ?
C3 N2 1.459(7) . ?
C4 C5 1.357(7) . ?
N2 O2 1.209(9) . ?
N2 O3 1.226(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
O1 N1 C1 122.3(7) . . ?
O1 N1 C5 121.5(10) . . ?
C1 N1 C5 116.3(12) . . ?
C2 C1 N1 124.9(7) . . ?
C1 C2 C3 116.1(7) . . ?
C1 C2 C6 117.1(6) . . ?
C3 C2 C6 126.8(8) . . ?
C4 C3 C2 121.4(8) . . ?
C4 C3 N2 117.0(5) . . ?
C2 C3 N2 121.6(6) . . ?
C5 C4 C3 120.6(6) . . ?
C4 C5 N1 120.6(8) . . ?
O2 N2 O3 124.5(10) . . ?
O2 N2 C3 118.5(7) . . ?
O3 N2 C3 116.9(7) . . ?

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
O1 N1 C1 C2 177.3(9) . . . . ?
C5 N1 C1 C2 -1.9(12) . . . . ?
N1 C1 C2 C3 0.2(11) . . . . ?
N1 C1 C2 C6 178.1(7) . . . . ?
C1 C2 C3 C4 1.5(9) . . . . ?
C6 C2 C3 C4 -176.2(6) . . . . ?
C1 C2 C3 N2 -179.2(6) . . . . ?
C6 C2 C3 N2 3.1(8) . . . . ?
C2 C3 C4 C5 -1.4(9) . . . . ?
N2 C3 C4 C5 179.3(5) . . . . ?
C3 C4 C5 N1 -0.5(9) . . . . ?
O1 N1 C5 C4 -177.3(7) . . . . ?
C1 N1 C5 C4 2.0(10) . . . . ?
C4 C3 N2 O2 -163.6(7) . . . . ?
C2 C3 N2 O2 17.1(8) . . . . ?
C4 C3 N2 O3 13.2(7) . . . . ?
C2 C3 N2 O3 -166.2(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.278
_diffrn_reflns_theta_full        27.09
_diffrn_measured_fraction_theta_full 0.278
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.105
_refine_diff_density_rms         0.025
_database_code_depnum_ccdc_archive 'CCDC 979873'
#######################################################################
#
#                 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_3-methyl-4-nitropyridine_N-oxide_0.26GPa

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-methyl-4-nitropyridineN-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13

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           Orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   21.215(4)
_cell_length_b                   6.128(5)
_cell_length_c                   5.1180(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     665.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       260000
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.5614
_exptl_absorpt_correction_T_max  0.9187
_exptl_absorpt_process_details   
;   
Katrusiak, A. (2003). REDSHABS - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Poznań.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467
;
_exptl_special_details           
; 
 Data were collected at room temperature and pressure of 0.26(3) GPa
 (260000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique.
 Pressure was determined by monitoring the shift of the ruby
 R1-fluorescence line.
;

_diffrn_ambient_temperature      296(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            2497
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.84
_diffrn_reflns_theta_max         27.16
_reflns_number_total             351
_reflns_number_gt                283
_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          
; 
 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)+(0.0569P)²+0.0905P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.067(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3(7)
_refine_ls_number_reflns         351
_refine_ls_number_parameters     101
_refine_ls_number_restraints     70
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1076
_refine_ls_wR_factor_gt          0.0969
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_restrained_S_all      1.084
_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
N1 N 0.15393(18) 0.051(3) 0.5041(9) 0.049(4) Uani 1 1 d DU . .
C1 C 0.1788(2) 0.188(3) 0.3169(10) 0.043(4) Uani 1 1 d DU . .
H1 H 0.2165 0.1479 0.2382 0.052 Uiso 1 1 calc R . .
C2 C 0.15244(18) 0.375(3) 0.2416(8) 0.036(4) Uani 1 1 d DU . .
C3 C 0.09696(19) 0.434(2) 0.3672(8) 0.038(4) Uani 1 1 d DU . .
C4 C 0.07178(19) 0.307(3) 0.5643(9) 0.043(4) Uani 1 1 d DU . .
H2 H 0.0352 0.3518 0.6492 0.051 Uiso 1 1 calc R . .
C5 C 0.09986(19) 0.119(3) 0.6340(9) 0.045(4) Uani 1 1 d DU . .
H3 H 0.0832 0.0354 0.7687 0.054 Uiso 1 1 calc R . .
O1 O 0.18035(17) -0.132(2) 0.5674(8) 0.081(4) Uani 1 1 d U . .
C6 C 0.18661(17) 0.521(3) 0.0396(8) 0.052(4) Uani 1 1 d U . .
H4 H 0.2236 0.4467 -0.0228 0.078 Uiso 1 1 calc R . .
H5 H 0.1986 0.6558 0.1204 0.078 Uiso 1 1 calc R . .
H6 H 0.1589 0.5498 -0.1044 0.078 Uiso 1 1 calc R . .
N2 N 0.06255(16) 0.640(3) 0.3029(8) 0.053(4) Uani 1 1 d U . .
O2 O 0.07502(15) 0.728(3) 0.0999(7) 0.077(4) Uani 1 1 d U . .
O3 O 0.02213(14) 0.698(2) 0.4554(6) 0.066(4) Uani 1 1 d U . .

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
N1 0.046(2) 0.041(13) 0.058(3) 0.012(5) -0.011(2) -0.008(5)
C1 0.036(2) 0.038(13) 0.055(3) 0.010(7) 0.000(2) 0.002(5)
C2 0.035(2) 0.039(13) 0.035(2) 0.003(6) -0.0020(16) -0.007(5)
C3 0.0353(19) 0.036(13) 0.042(2) 0.013(5) -0.0042(17) 0.003(5)
C4 0.037(2) 0.038(13) 0.052(3) -0.004(7) -0.002(2) -0.001(6)
C5 0.041(2) 0.043(13) 0.052(3) -0.007(6) 0.0033(18) -0.009(5)
O1 0.068(2) 0.086(13) 0.090(3) 0.013(7) -0.008(2) 0.008(5)
C6 0.048(2) 0.051(13) 0.057(2) 0.002(7) 0.0010(17) -0.005(5)
N2 0.0398(18) 0.054(13) 0.064(2) 0.000(6) 0.000(2) 0.010(5)
O2 0.0754(19) 0.076(12) 0.080(2) 0.027(6) 0.0135(17) 0.017(4)
O3 0.0639(17) 0.056(12) 0.0787(19) 0.009(6) 0.0063(16) 0.023(4)

_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
N1 O1 1.295(19) . ?
N1 C1 1.382(17) . ?
N1 C5 1.391(9) . ?
C1 C2 1.331(19) . ?
C2 C3 1.388(8) . ?
C2 C6 1.545(16) . ?
C3 C4 1.380(9) . ?
C3 N2 1.497(19) . ?
C4 C5 1.34(2) . ?
N2 O2 1.200(10) . ?
N2 O3 1.213(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
O1 N1 C1 122.5(7) . . ?
O1 N1 C5 120.0(10) . . ?
C1 N1 C5 117.5(12) . . ?
C2 C1 N1 124.5(7) . . ?
C1 C2 C3 116.3(8) . . ?
C1 C2 C6 119.5(6) . . ?
C3 C2 C6 124.0(12) . . ?
C4 C3 C2 121.5(10) . . ?
C4 C3 N2 116.5(6) . . ?
C2 C3 N2 122.0(8) . . ?
C5 C4 C3 120.2(7) . . ?
C4 C5 N1 119.8(10) . . ?
O2 N2 O3 125.5(12) . . ?
O2 N2 C3 117.6(8) . . ?
O3 N2 C3 116.8(7) . . ?

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
O1 N1 C1 C2 178.3(9) . . . . ?
C5 N1 C1 C2 -4.3(13) . . . . ?
N1 C1 C2 C3 1.4(12) . . . . ?
N1 C1 C2 C6 177.1(7) . . . . ?
C1 C2 C3 C4 1.8(10) . . . . ?
C6 C2 C3 C4 -173.6(7) . . . . ?
C1 C2 C3 N2 179.7(9) . . . . ?
C6 C2 C3 N2 4.3(10) . . . . ?
C2 C3 C4 C5 -2.0(12) . . . . ?
N2 C3 C4 C5 -180.0(9) . . . . ?
C3 C4 C5 N1 -1.0(13) . . . . ?
O1 N1 C5 C4 -178.6(10) . . . . ?
C1 N1 C5 C4 4.0(12) . . . . ?
C4 C3 N2 O2 -164.5(8) . . . . ?
C2 C3 N2 O2 17.6(12) . . . . ?
C4 C3 N2 O3 12.1(10) . . . . ?
C2 C3 N2 O3 -165.9(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.275
_diffrn_reflns_theta_full        27.16
_diffrn_measured_fraction_theta_full 0.275
_refine_diff_density_max         0.070
_refine_diff_density_min         -0.075
_refine_diff_density_rms         0.022
_database_code_depnum_ccdc_archive 'CCDC 979874'
#######################################################################
#
#                 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_3-methyl-4-nitropyridine_N-oxide_0.34GPa
_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-methyl-4-nitropyridineN-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13

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           Orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   21.148(5)
_cell_length_b                   6.121(5)
_cell_length_c                   5.1082(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     661.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       340000
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.5709
_exptl_absorpt_correction_T_max  0.9283
_exptl_absorpt_process_details   
;   
Katrusiak, A. (2003). REDSHABS - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Poznań.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467
;
_exptl_special_details           
; 
 Data were collected at room temperature and pressure of 0.34(3) GPa
 (340000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique.
 Pressure was determined by monitoring the shift of the ruby
 R1-fluorescence line.
;
_diffrn_ambient_temperature      296(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  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       
;HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2514
_diffrn_reflns_av_R_equivalents  0.0715
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.85
_diffrn_reflns_theta_max         27.16
_reflns_number_total             349
_reflns_number_gt                282
_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          
; 
 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)+(0.0437P)²+0.1778P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.072(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   4(7)
_refine_ls_number_reflns         349
_refine_ls_number_parameters     101
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1104
_refine_ls_wR_factor_gt          0.1003
_refine_ls_goodness_of_fit_ref   1.203
_refine_ls_restrained_S_all      1.118
_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
N1 N 0.1537(2) 0.0532(19) 0.5026(10) 0.054(5) Uani 1 1 d DU . .
C1 C 0.1784(2) 0.187(2) 0.3160(11) 0.043(4) Uani 1 1 d DU . .
H1 H 0.2156 0.1424 0.2345 0.051 Uiso 1 1 calc R . .
C2 C 0.1521(2) 0.384(2) 0.2381(8) 0.038(4) Uani 1 1 d DU . .
C3 C 0.0972(2) 0.4337(18) 0.3652(9) 0.039(4) Uani 1 1 d DU . .
C4 C 0.0717(2) 0.3064(19) 0.5612(10) 0.047(4) Uani 1 1 d DU . .
H2 H 0.0352 0.3519 0.6463 0.056 Uiso 1 1 calc R . .
C5 C 0.0995(2) 0.115(2) 0.6312(10) 0.049(5) Uani 1 1 d DU . .
H3 H 0.0823 0.0282 0.7625 0.058 Uiso 1 1 calc R . .
O1 O 0.1796(2) -0.132(2) 0.5655(10) 0.083(4) Uani 1 1 d DU . .
C6 C 0.1873(2) 0.516(3) 0.0376(9) 0.054(4) Uani 1 1 d DU . .
H4 H 0.2239 0.4369 -0.0199 0.080 Uiso 1 1 calc R . .
H5 H 0.2003 0.6524 0.1141 0.080 Uiso 1 1 calc R . .
H6 H 0.1602 0.5444 -0.1093 0.080 Uiso 1 1 calc R . .
N2 N 0.06273(19) 0.6334(19) 0.3049(10) 0.049(4) Uani 1 1 d DU . .
O2 O 0.07521(17) 0.727(3) 0.1002(9) 0.081(4) Uani 1 1 d U . .
O3 O 0.02183(16) 0.6953(19) 0.4537(7) 0.070(4) Uani 1 1 d U . .

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
N1 0.052(3) 0.048(13) 0.063(3) 0.010(6) -0.008(2) -0.002(5)
C1 0.036(2) 0.041(13) 0.051(3) 0.007(7) 0.005(2) -0.009(5)
C2 0.041(2) 0.034(13) 0.038(3) 0.001(6) -0.0091(19) 0.000(5)
C3 0.034(2) 0.035(13) 0.048(3) 0.003(6) -0.007(2) 0.003(5)
C4 0.041(2) 0.045(13) 0.054(3) 0.002(7) 0.004(2) -0.004(6)
C5 0.051(3) 0.046(13) 0.049(3) 0.002(6) 0.002(2) 0.009(6)
O1 0.076(3) 0.083(13) 0.091(3) 0.013(7) -0.004(2) 0.004(6)
C6 0.053(2) 0.055(13) 0.053(3) -0.002(7) 0.0049(19) -0.015(6)
N2 0.042(2) 0.049(13) 0.057(3) -0.007(6) 0.000(2) 0.000(5)
O2 0.082(2) 0.079(12) 0.082(2) 0.020(6) 0.0079(19) 0.018(4)
O3 0.067(2) 0.066(12) 0.078(2) 0.001(6) 0.0139(17) 0.029(5)

_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
N1 O1 1.298(7) . ?
N1 C1 1.359(6) . ?
N1 C5 1.374(6) . ?
C1 C2 1.385(7) . ?
C2 C3 1.365(8) . ?
C2 C6 1.504(7) . ?
C3 C4 1.378(6) . ?
C3 N2 1.457(7) . ?
C4 C5 1.358(7) . ?
N2 O3 1.212(6) . ?
N2 O2 1.222(9) . ?

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
O1 N1 C1 122.4(6) . . ?
O1 N1 C5 118.3(8) . . ?
C1 N1 C5 119.3(7) . . ?
N1 C1 C2 124.8(6) . . ?
C3 C2 C1 113.5(7) . . ?
C3 C2 C6 128.5(8) . . ?
C1 C2 C6 117.9(6) . . ?
C2 C3 C4 123.4(9) . . ?
C2 C3 N2 120.9(6) . . ?
C4 C3 N2 115.6(6) . . ?
C5 C4 C3 120.6(7) . . ?
C4 C5 N1 118.2(8) . . ?
O3 N2 O2 123.0(10) . . ?
O3 N2 C3 119.2(7) . . ?
O2 N2 C3 117.8(7) . . ?

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
O1 N1 C1 C2 178.8(5) . . . . ?
C5 N1 C1 C2 -1.3(8) . . . . ?
N1 C1 C2 C3 -0.9(7) . . . . ?
N1 C1 C2 C6 177.1(5) . . . . ?
C1 C2 C3 C4 2.9(8) . . . . ?
C6 C2 C3 C4 -174.8(6) . . . . ?
C1 C2 C3 N2 -179.1(5) . . . . ?
C6 C2 C3 N2 3.2(8) . . . . ?
C2 C3 C4 C5 -2.8(9) . . . . ?
N2 C3 C4 C5 179.1(5) . . . . ?
C3 C4 C5 N1 0.4(8) . . . . ?
O1 N1 C5 C4 -178.6(5) . . . . ?
C1 N1 C5 C4 1.5(8) . . . . ?
C2 C3 N2 O3 -165.4(7) . . . . ?
C4 C3 N2 O3 12.7(7) . . . . ?
C2 C3 N2 O2 17.0(8) . . . . ?
C4 C3 N2 O2 -164.9(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.274
_diffrn_reflns_theta_full        27.16
_diffrn_measured_fraction_theta_full 0.274
_refine_diff_density_max         0.080
_refine_diff_density_min         -0.064
_refine_diff_density_rms         0.019
_database_code_depnum_ccdc_archive 'CCDC 979875'
#######################################################################
#
#                 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_3-methyl-4-nitropyridine_N-oxide_0.40GPa

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-methyl-4-nitropyridine_N-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13

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           Orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   21.101(4)
_cell_length_b                   6.112(5)
_cell_length_c                   5.0990(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     657.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       400000
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.5537
_exptl_absorpt_correction_T_max  0.9241
_exptl_absorpt_process_details   
;   
Katrusiak, A. (2003). REDSHABS - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Poznań.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467
;
_exptl_special_details           
; 
 Data were collected at room temperature and pressure of 0.40(3) GPa
 (400000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique.
 Pressure was determined by monitoring the shift of the ruby
 R1-fluorescence line.
;
_diffrn_ambient_temperature      296(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  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       
;HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2339
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.86
_diffrn_reflns_theta_max         27.22
_reflns_number_total             305
_reflns_number_gt                268
_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          
; 
 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)+(0.0133P)²+0.8177P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.094(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3(9)
_refine_ls_number_reflns         305
_refine_ls_number_parameters     101
_refine_ls_number_restraints     81
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0943
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.036
_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
N1 N 0.1531(2) 0.046(2) 0.5019(12) 0.052(5) Uani 1 1 d DU . .
C1 C 0.1776(3) 0.176(2) 0.3113(13) 0.042(5) Uani 1 1 d DU . .
H1 H 0.2140 0.1282 0.2258 0.050 Uiso 1 1 calc R . .
C2 C 0.1519(3) 0.374(3) 0.2363(11) 0.040(5) Uani 1 1 d DU . .
C3 C 0.0968(3) 0.430(3) 0.3635(11) 0.038(5) Uani 1 1 d DU . .
C4 C 0.0700(3) 0.302(2) 0.5557(11) 0.048(5) Uani 1 1 d DU . .
H2 H 0.0323 0.3440 0.6354 0.057 Uiso 1 1 calc R . .
C5 C 0.0990(3) 0.113(2) 0.6275(11) 0.040(5) Uani 1 1 d DU . .
H3 H 0.0822 0.0293 0.7626 0.048 Uiso 1 1 calc RD . .
O1 O 0.1804(2) -0.137(2) 0.5632(11) 0.073(5) Uani 1 1 d DU . .
C6 C 0.1863(3) 0.507(3) 0.0348(11) 0.054(5) Uani 1 1 d DU . .
H4 H 0.2230 0.4287 -0.0238 0.081 Uiso 1 1 calc R . .
H5 H 0.1991 0.6441 0.1106 0.081 Uiso 1 1 calc R . .
H6 H 0.1587 0.5342 -0.1115 0.081 Uiso 1 1 calc RD . .
N2 N 0.0626(3) 0.631(3) 0.3030(12) 0.052(5) Uani 1 1 d DU . .
O2 O 0.0748(2) 0.732(3) 0.1006(11) 0.078(5) Uani 1 1 d U . .
O3 O 0.0210(2) 0.701(3) 0.4480(9) 0.068(5) Uani 1 1 d U . .

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
N1 0.039(3) 0.051(14) 0.065(4) 0.003(7) -0.019(3) 0.003(6)
C1 0.043(3) 0.038(14) 0.045(4) 0.001(8) -0.001(3) -0.015(7)
C2 0.044(3) 0.038(14) 0.040(3) 0.005(7) -0.006(3) 0.005(7)
C3 0.032(2) 0.036(14) 0.047(4) 0.005(7) -0.001(2) 0.011(7)
C4 0.038(3) 0.044(14) 0.061(4) 0.009(8) 0.000(3) 0.017(7)
C5 0.042(3) 0.036(14) 0.043(3) 0.001(7) 0.004(2) -0.022(7)
O1 0.056(3) 0.073(14) 0.091(4) 0.006(8) -0.013(3) -0.007(6)
C6 0.053(3) 0.056(14) 0.053(4) -0.001(8) 0.006(3) -0.019(7)
N2 0.045(3) 0.052(14) 0.058(3) 0.003(7) 0.004(3) 0.001(7)
O2 0.077(3) 0.076(14) 0.081(3) 0.014(8) 0.007(3) 0.014(6)
O3 0.061(3) 0.065(14) 0.078(3) 0.010(7) 0.011(2) 0.019(6)

_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
N1 O1 1.297(8) . ?
N1 C1 1.357(7) . ?
N1 C5 1.372(7) . ?
C1 C2 1.383(8) . ?
C2 C3 1.374(10) . ?
C2 C6 1.497(7) . ?
C3 C4 1.377(7) . ?
C3 N2 1.459(8) . ?
C4 C5 1.354(8) . ?
N2 O3 1.226(10) . ?
N2 O2 1.230(12) . ?

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
O1 N1 C1 120.5(7) . . ?
O1 N1 C5 121.0(8) . . ?
C1 N1 C5 118.5(9) . . ?
N1 C1 C2 124.1(7) . . ?
C3 C2 C1 114.7(8) . . ?
C3 C2 C6 126.8(9) . . ?
C1 C2 C6 118.4(8) . . ?
C2 C3 C4 123.0(10) . . ?
C2 C3 N2 121.8(8) . . ?
C4 C3 N2 115.2(7) . . ?
C5 C4 C3 119.3(8) . . ?
C4 C5 N1 120.3(9) . . ?
O3 N2 O2 118.6(13) . . ?
O3 N2 C3 121.5(9) . . ?
O2 N2 C3 119.8(8) . . ?

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
O1 N1 C1 C2 -179.2(6) . . . . ?
C5 N1 C1 C2 0.8(10) . . . . ?
N1 C1 C2 C3 -2.5(9) . . . . ?
N1 C1 C2 C6 176.1(7) . . . . ?
C1 C2 C3 C4 1.7(9) . . . . ?
C6 C2 C3 C4 -176.9(7) . . . . ?
C1 C2 C3 N2 -178.4(6) . . . . ?
C6 C2 C3 N2 3.1(10) . . . . ?
C2 C3 C4 C5 1.0(10) . . . . ?
N2 C3 C4 C5 -179.0(6) . . . . ?
C3 C4 C5 N1 -2.9(10) . . . . ?
O1 N1 C5 C4 -177.9(6) . . . . ?
C1 N1 C5 C4 2.1(10) . . . . ?
C2 C3 N2 O3 -165.7(9) . . . . ?
C4 C3 N2 O3 14.3(11) . . . . ?
C2 C3 N2 O2 15.2(11) . . . . ?
C4 C3 N2 O2 -164.8(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.249
_diffrn_reflns_theta_full        27.22
_diffrn_measured_fraction_theta_full 0.249
_refine_diff_density_max         0.081
_refine_diff_density_min         -0.067
_refine_diff_density_rms         0.020
_database_code_depnum_ccdc_archive 'CCDC 979876'
#######################################################################
#
#                 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_3-methyl-4-nitropyridine_N-oxide_0.52GPa

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-methyl-4-nitropyridine_N-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13

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           Orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   20.994(8)
_cell_length_b                   6.105(7)
_cell_length_c                   5.0903(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     652.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       520000
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.5752
_exptl_absorpt_correction_T_max  0.9284
_exptl_absorpt_process_details   
;   
Katrusiak, A. (2003). REDSHABS - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Poznań.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467
;
_exptl_special_details           
; 
 Data were collected at room temperature and pressure of 0.52(3) GPa
 (520000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique.
 Pressure was determined by monitoring the shift of the ruby
 R1-fluorescence line.
;
_diffrn_ambient_temperature      296(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  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       
;HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2393
_diffrn_reflns_av_R_equivalents  0.1983
_diffrn_reflns_av_sigmaI/netI    0.0795
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.88
_diffrn_reflns_theta_max         27.14
_reflns_number_total             360
_reflns_number_gt                282
_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          
; 
 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)+(0.0532P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_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   8(8)
_refine_ls_number_reflns         360
_refine_ls_number_parameters     100
_refine_ls_number_restraints     87
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1276
_refine_ls_wR_factor_gt          0.1165
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.061
_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
N1 N 0.15395(17) 0.0464(18) 0.5063(10) 0.045(4) Uani 1 1 d DU . .
C1 C 0.1784(2) 0.177(2) 0.3141(10) 0.046(5) Uani 1 1 d DU . .
H1 H 0.2153 0.1292 0.2309 0.055 Uiso 1 1 calc R . .
C2 C 0.1530(2) 0.376(2) 0.2318(8) 0.037(4) Uani 1 1 d DU . .
C3 C 0.0966(2) 0.4358(19) 0.3606(9) 0.040(5) Uani 1 1 d DU . .
C4 C 0.0706(2) 0.3123(19) 0.5609(10) 0.044(5) Uani 1 1 d DU . .
H2 H 0.0343 0.3596 0.6490 0.053 Uiso 1 1 calc R . .
C5 C 0.0992(2) 0.1195(19) 0.6266(10) 0.044(5) Uani 1 1 d DU . .
H3 H 0.0810 0.0340 0.7578 0.053 Uiso 1 1 calc R . .
O1 O 0.18028(17) -0.1418(19) 0.5606(10) 0.089(5) Uani 1 1 d DU . .
C6 C 0.1881(2) 0.509(2) 0.0315(8) 0.048(5) Uani 1 1 d DU . .
H4 H 0.2250 0.4298 -0.0269 0.072 Uiso 1 1 calc R . .
H5 H 0.2012 0.6454 0.1086 0.072 Uiso 1 1 calc R . .
H6 H 0.1607 0.5374 -0.1155 0.072 Uiso 1 1 calc R . .
N2 N 0.06295(18) 0.639(2) 0.3038(9) 0.048(4) Uani 1 1 d DU . .
O2 O 0.07458(16) 0.734(2) 0.0957(8) 0.076(2) Uani 1 1 d U . .
O3 O 0.02041(16) 0.6956(19) 0.4520(7) 0.067(4) Uani 1 1 d U . .

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
N1 0.035(2) 0.043(13) 0.058(3) 0.010(6) -0.003(2) -0.006(5)
C1 0.040(2) 0.045(13) 0.053(3) 0.013(7) -0.003(3) -0.006(5)
C2 0.032(2) 0.038(13) 0.041(3) 0.013(6) -0.0058(18) -0.011(5)
C3 0.034(2) 0.038(13) 0.048(3) 0.006(6) -0.008(2) 0.001(6)
C4 0.032(2) 0.043(13) 0.057(3) 0.013(7) 0.009(2) -0.001(5)
C5 0.038(2) 0.041(13) 0.052(3) 0.000(6) -0.006(2) -0.004(6)
O1 0.065(2) 0.096(13) 0.105(4) 0.006(8) -0.009(3) 0.031(5)
C6 0.048(2) 0.044(13) 0.053(3) 0.005(7) 0.005(2) 0.003(7)
N2 0.0353(19) 0.045(13) 0.063(3) -0.001(6) -0.003(2) 0.004(5)
O2 0.072(2) 0.078(6) 0.079(2) 0.008(4) 0.0055(19) 0.008(4)
O3 0.0572(18) 0.068(13) 0.075(2) 0.014(6) 0.0136(16) 0.030(5)

_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
N1 O1 1.305(7) . ?
N1 C1 1.363(6) . ?
N1 C5 1.376(6) . ?
C1 C2 1.389(7) . ?
C2 C3 1.403(8) . ?
C2 C6 1.498(7) . ?
C3 C4 1.381(7) . ?
C3 N2 1.456(7) . ?
C4 C5 1.363(7) . ?
N2 O3 1.219(6) . ?
N2 O2 1.233(9) . ?

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
O1 N1 C1 120.5(6) . . ?
O1 N1 C5 123.0(7) . . ?
C1 N1 C5 116.3(7) . . ?
N1 C1 C2 125.7(5) . . ?
C1 C2 C3 114.3(6) . . ?
C1 C2 C6 119.4(5) . . ?
C3 C2 C6 126.2(8) . . ?
C4 C3 C2 122.4(8) . . ?
C4 C3 N2 114.8(6) . . ?
C2 C3 N2 122.7(6) . . ?
C5 C4 C3 118.6(7) . . ?
C4 C5 N1 122.6(7) . . ?
O3 N2 O2 122.8(10) . . ?
O3 N2 C3 118.3(7) . . ?
O2 N2 C3 118.5(7) . . ?

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
O1 N1 C1 C2 177.1(5) . . . . ?
C5 N1 C1 C2 0.3(8) . . . . ?
N1 C1 C2 C3 -1.5(7) . . . . ?
N1 C1 C2 C6 175.5(6) . . . . ?
C1 C2 C3 C4 3.0(8) . . . . ?
C6 C2 C3 C4 -173.7(6) . . . . ?
C1 C2 C3 N2 179.5(5) . . . . ?
C6 C2 C3 N2 2.8(8) . . . . ?
C2 C3 C4 C5 -3.3(9) . . . . ?
N2 C3 C4 C5 180.0(5) . . . . ?
C3 C4 C5 N1 1.9(8) . . . . ?
O1 N1 C5 C4 -177.2(6) . . . . ?
C1 N1 C5 C4 -0.4(8) . . . . ?
C4 C3 N2 O3 8.3(7) . . . . ?
C2 C3 N2 O3 -168.4(7) . . . . ?
C4 C3 N2 O2 -164.9(7) . . . . ?
C2 C3 N2 O2 18.3(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.282
_diffrn_reflns_theta_full        27.14
_diffrn_measured_fraction_theta_full 0.282
_refine_diff_density_max         0.079
_refine_diff_density_min         -0.092
_refine_diff_density_rms         0.026
_database_code_depnum_ccdc_archive 'CCDC 979877'
#######################################################################
#
#                 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_3-methyl-4-nitropyridine_N-oxide_0.83GPa

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-methyl-4-nitropyridineN-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13

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           Orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   20.771(4)
_cell_length_b                   6.075(4)
_cell_length_c                   5.0621(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     638.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       830000
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.5836
_exptl_absorpt_correction_T_max  0.9236
_exptl_absorpt_process_details   
;   
Katrusiak, A. (2003). REDSHABS - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Poznań.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467
;
_exptl_special_details           
; 
 Data were collected at room temperature and pressure of 0.83(3) GPa
 (830000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique.
 Pressure was determined by monitoring the shift of the ruby
 R1-fluorescence line.
;
_diffrn_ambient_temperature      296(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  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       
;HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2242
_diffrn_reflns_av_R_equivalents  0.0956
_diffrn_reflns_av_sigmaI/netI    0.0570
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         5.63
_diffrn_reflns_theta_max         27.04
_reflns_number_total             327
_reflns_number_gt                296
_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          
; 
 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)+(0.0000P)²+0.4669P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_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(7)
_refine_ls_number_reflns         327
_refine_ls_number_parameters     100
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_ref         0.0950
_refine_ls_wR_factor_gt          0.0912
_refine_ls_goodness_of_fit_ref   1.220
_refine_ls_restrained_S_all      1.159
_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
N1 N 0.1534(2) 0.051(2) 0.4983(11) 0.039(5) Uani 1 1 d DU . .
C1 C 0.1784(3) 0.180(3) 0.3067(12) 0.038(5) Uani 1 1 d DU . .
H1 H 0.2152 0.1310 0.2202 0.046 Uiso 1 1 calc R . .
C2 C 0.1522(3) 0.3815(19) 0.2307(9) 0.028(4) Uani 1 1 d DU . .
C3 C 0.0963(3) 0.445(2) 0.3606(10) 0.029(4) Uani 1 1 d DU . .
C4 C 0.0721(3) 0.3198(16) 0.5612(13) 0.045(5) Uani 1 1 d DU . .
H2 H 0.0365 0.3707 0.6542 0.054 Uiso 1 1 calc R . .
C5 C 0.0988(3) 0.1211(17) 0.6299(12) 0.045(5) Uani 1 1 d DU . .
H3 H 0.0805 0.0354 0.7624 0.054 Uiso 1 1 calc R . .
O1 O 0.1795(2) -0.137(2) 0.5581(10) 0.068(5) Uani 1 1 d DU . .
C6 C 0.1882(3) 0.513(3) 0.0288(9) 0.047(5) Uani 1 1 d DU . .
H4 H 0.2253 0.4323 -0.0290 0.071 Uiso 1 1 calc R . .
H5 H 0.2018 0.6504 0.1056 0.071 Uiso 1 1 calc R . .
H6 H 0.1607 0.5423 -0.1195 0.071 Uiso 1 1 calc R . .
N2 N 0.0621(2) 0.648(2) 0.2994(9) 0.039(4) Uani 1 1 d DU . .
O2 O 0.07552(19) 0.7350(18) 0.0913(9) 0.061(4) Uani 1 1 d DU . .
O3 O 0.02056(18) 0.7075(16) 0.4541(8) 0.057(4) Uani 1 1 d DU . .

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
N1 0.026(2) 0.039(13) 0.053(3) -0.005(6) -0.004(2) -0.002(5)
C1 0.031(3) 0.037(13) 0.046(3) 0.003(7) 0.000(3) -0.008(6)
C2 0.039(3) 0.023(13) 0.022(2) -0.010(6) 0.004(2) -0.008(6)
C3 0.028(2) 0.031(13) 0.029(3) -0.005(6) -0.007(2) 0.003(6)
C4 0.038(3) 0.042(13) 0.057(4) 0.012(7) 0.008(3) -0.011(7)
C5 0.045(3) 0.041(14) 0.050(4) 0.006(7) 0.005(3) -0.007(7)
O1 0.057(3) 0.069(13) 0.077(3) -0.004(7) -0.012(2) 0.015(6)
C6 0.055(3) 0.045(13) 0.042(3) 0.002(7) -0.005(2) 0.009(6)
N2 0.028(2) 0.041(13) 0.049(3) 0.007(6) -0.008(2) 0.003(5)
O2 0.066(2) 0.057(13) 0.060(2) 0.027(6) 0.0071(19) 0.005(5)
O3 0.049(2) 0.050(13) 0.074(3) 0.004(6) 0.0177(19) 0.018(5)

_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
N1 O1 1.301(7) . ?
N1 C1 1.349(7) . ?
N1 C5 1.383(7) . ?
C1 C2 1.395(15) . ?
C2 C3 1.389(8) . ?
C2 C6 1.499(7) . ?
C3 C4 1.364(11) . ?
C3 N2 1.460(7) . ?
C4 C5 1.373(7) . ?
N2 O2 1.210(8) . ?
N2 O3 1.219(7) . ?

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
O1 N1 C1 121.1(7) . . ?
O1 N1 C5 120.0(7) . . ?
C1 N1 C5 118.9(8) . . ?
N1 C1 C2 123.9(7) . . ?
C3 C2 C1 116.0(8) . . ?
C3 C2 C6 126.3(8) . . ?
C1 C2 C6 117.6(7) . . ?
C4 C3 C2 120.4(10) . . ?
C4 C3 N2 116.7(6) . . ?
C2 C3 N2 122.8(7) . . ?
C3 C4 C5 122.0(7) . . ?
C4 C5 N1 118.7(8) . . ?
O2 N2 O3 126.5(10) . . ?
O2 N2 C3 116.1(7) . . ?
O3 N2 C3 117.3(7) . . ?

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
O1 N1 C1 C2 179.0(7) . . . . ?
C5 N1 C1 C2 -0.3(10) . . . . ?
N1 C1 C2 C3 -1.6(10) . . . . ?
N1 C1 C2 C6 175.5(6) . . . . ?
C1 C2 C3 C4 4.1(9) . . . . ?
C6 C2 C3 C4 -172.8(6) . . . . ?
C1 C2 C3 N2 -178.4(6) . . . . ?
C6 C2 C3 N2 4.8(8) . . . . ?
C2 C3 C4 C5 -4.8(11) . . . . ?
N2 C3 C4 C5 177.5(6) . . . . ?
C3 C4 C5 N1 2.7(10) . . . . ?
O1 N1 C5 C4 -179.5(6) . . . . ?
C1 N1 C5 C4 -0.2(9) . . . . ?
C4 C3 N2 O2 -165.8(8) . . . . ?
C2 C3 N2 O2 16.6(8) . . . . ?
C4 C3 N2 O3 10.3(7) . . . . ?
C2 C3 N2 O3 -167.3(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.261
_diffrn_reflns_theta_full        27.04
_diffrn_measured_fraction_theta_full 0.261
_refine_diff_density_max         0.073
_refine_diff_density_min         -0.066
_refine_diff_density_rms         0.020
_database_code_depnum_ccdc_archive 'CCDC 979878'


#######################################################################
#
#                 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_3-methyl-4-nitropyridine-N-oxide_120K

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-methyl-4-nitropyridine-N-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13

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           Orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   20.9533(7)
_cell_length_b                   6.1092(2)
_cell_length_c                   5.1332(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     657.09(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9628
_exptl_absorpt_correction_T_max  0.9749
_exptl_absorpt_process_details   '(CrysAlis Pro; Oxford Diffraction, 2010)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(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  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1840
_diffrn_reflns_av_R_equivalents  0.0122
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         3.47
_diffrn_reflns_theta_max         28.94
_reflns_number_total             930
_reflns_number_gt                886
_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          
; 
 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)+(0.0376P)²+0.1306P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.023(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_number_reflns         930
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0282
_refine_ls_wR_factor_ref         0.0764
_refine_ls_wR_factor_gt          0.0739
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_restrained_S_all      1.144
_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
N1 N 0.15327(6) 0.0514(2) 0.4964(3) 0.0183(3) Uani 1 1 d . . .
C1 C 0.17901(7) 0.1804(3) 0.3074(3) 0.0182(3) Uani 1 1 d . . .
H1 H 0.2159 0.1332 0.2240 0.022 Uiso 1 1 calc R . .
C2 C 0.15259(7) 0.3794(3) 0.2338(3) 0.0166(3) Uani 1 1 d . . .
C3 C 0.09672(7) 0.4406(3) 0.3654(3) 0.0162(3) Uani 1 1 d . . .
C4 C 0.07122(7) 0.3123(3) 0.5629(3) 0.0178(3) Uani 1 1 d . . .
H2 H 0.0349 0.3580 0.6514 0.021 Uiso 1 1 calc R . .
C5 C 0.09999(7) 0.1172(3) 0.6269(3) 0.0193(3) Uani 1 1 d . . .
H3 H 0.0831 0.0304 0.7589 0.023 Uiso 1 1 calc R . .
O1 O 0.17978(5) -0.13501(19) 0.5535(3) 0.0261(3) Uani 1 1 d . . .
C6 C 0.18780(8) 0.5111(3) 0.0330(3) 0.0207(3) Uani 1 1 d . . .
H4 H 0.2246 0.4311 -0.0245 0.031 Uiso 1 1 calc R . .
H5 H 0.2011 0.6477 0.1079 0.031 Uiso 1 1 calc R . .
H6 H 0.1602 0.5387 -0.1127 0.031 Uiso 1 1 calc R . .
N2 N 0.06273(6) 0.6436(2) 0.3035(3) 0.0197(3) Uani 1 1 d . . .
O2 O 0.07540(6) 0.7378(2) 0.0990(3) 0.0311(3) Uani 1 1 d . . .
O3 O 0.02221(6) 0.7091(2) 0.4580(3) 0.0260(3) Uani 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
N1 0.0180(6) 0.0146(6) 0.0222(7) 0.0027(6) -0.0047(6) 0.0000(5)
C1 0.0164(7) 0.0189(7) 0.0194(7) 0.0001(7) -0.0002(6) -0.0002(6)
C2 0.0162(7) 0.0175(7) 0.0160(7) 0.0001(6) -0.0025(6) -0.0024(6)
C3 0.0158(7) 0.0150(7) 0.0178(7) 0.0002(7) -0.0037(6) -0.0003(6)
C4 0.0154(7) 0.0200(7) 0.0180(7) -0.0006(7) 0.0003(6) -0.0020(6)
C5 0.0189(7) 0.0198(7) 0.0193(7) 0.0038(7) -0.0003(6) -0.0044(6)
O1 0.0267(6) 0.0168(5) 0.0349(7) 0.0074(6) -0.0039(6) 0.0050(5)
C6 0.0202(7) 0.0227(8) 0.0190(7) 0.0047(7) 0.0016(7) -0.0008(6)
N2 0.0184(6) 0.0182(6) 0.0226(7) 0.0023(6) -0.0029(6) 0.0012(5)
O2 0.0288(6) 0.0324(7) 0.0321(7) 0.0174(6) 0.0021(6) 0.0072(5)
O3 0.0240(6) 0.0247(6) 0.0294(6) -0.0030(6) 0.0031(5) 0.0070(5)

_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
N1 O1 1.3005(16) . ?
N1 C1 1.361(2) . ?
N1 C5 1.363(2) . ?
C1 C2 1.388(2) . ?
C2 C3 1.402(2) . ?
C2 C6 1.501(2) . ?
C3 C4 1.388(2) . ?
C3 N2 1.465(2) . ?
C4 C5 1.375(2) . ?
N2 O2 1.2259(18) . ?
N2 O3 1.2287(18) . ?

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
O1 N1 C1 119.89(14) . . ?
O1 N1 C5 119.83(14) . . ?
C1 N1 C5 120.28(13) . . ?
N1 C1 C2 122.89(14) . . ?
C1 C2 C3 115.80(14) . . ?
C1 C2 C6 117.40(14) . . ?
C3 C2 C6 126.74(14) . . ?
C4 C3 C2 121.49(14) . . ?
C4 C3 N2 116.70(14) . . ?
C2 C3 N2 121.81(14) . . ?
C5 C4 C3 119.68(15) . . ?
N1 C5 C4 119.81(15) . . ?
O2 N2 O3 123.33(14) . . ?
O2 N2 C3 118.52(14) . . ?
O3 N2 C3 118.14(13) . . ?

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
O1 N1 C1 C2 178.91(14) . . . . ?
C5 N1 C1 C2 -1.4(2) . . . . ?
N1 C1 C2 C3 -0.5(2) . . . . ?
N1 C1 C2 C6 176.73(14) . . . . ?
C1 C2 C3 C4 2.2(2) . . . . ?
C6 C2 C3 C4 -174.76(15) . . . . ?
C1 C2 C3 N2 -178.44(14) . . . . ?
C6 C2 C3 N2 4.6(2) . . . . ?
C2 C3 C4 C5 -2.0(2) . . . . ?
N2 C3 C4 C5 178.58(13) . . . . ?
O1 N1 C5 C4 -178.68(14) . . . . ?
C1 N1 C5 C4 1.6(2) . . . . ?
C3 C4 C5 N1 0.1(2) . . . . ?
C4 C3 N2 O2 -165.16(14) . . . . ?
C2 C3 N2 O2 15.4(2) . . . . ?
C4 C3 N2 O3 13.8(2) . . . . ?
C2 C3 N2 O3 -165.63(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.888
_diffrn_reflns_theta_full        28.94
_diffrn_measured_fraction_theta_full 0.888
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.037
_database_code_depnum_ccdc_archive 'CCDC 979897'
#######################################################################
#
#                 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_3-methyl-4-nitropyridine-N-oxide_135K

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-methyl-4-nitropyridine-N-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13

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           Orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   20.9915(8)
_cell_length_b                   6.1114(2)
_cell_length_c                   5.1337(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     658.59(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    135(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9627
_exptl_absorpt_correction_T_max  0.9747
_exptl_absorpt_process_details   '(CrysAlis Pro; Oxford Diffraction, 2010)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      135(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  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1845
_diffrn_reflns_av_R_equivalents  0.0115
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         3.47
_diffrn_reflns_theta_max         28.91
_reflns_number_total             930
_reflns_number_gt                890
_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          
; 
 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)+(0.0373P)²+0.0867P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.025(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_number_reflns         930
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0765
_refine_ls_wR_factor_gt          0.0752
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_restrained_S_all      1.195
_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
N1 N 0.15341(6) 0.0511(2) 0.4975(3) 0.0204(3) Uani 1 1 d . . .
C1 C 0.17909(7) 0.1802(3) 0.3088(3) 0.0199(3) Uani 1 1 d . . .
H1 H 0.2160 0.1333 0.2259 0.024 Uiso 1 1 calc R . .
C2 C 0.15256(7) 0.3789(3) 0.2344(3) 0.0180(3) Uani 1 1 d . . .
C3 C 0.09677(7) 0.4399(2) 0.3653(3) 0.0177(3) Uani 1 1 d . . .
C4 C 0.07117(7) 0.3112(3) 0.5628(3) 0.0197(3) Uani 1 1 d . . .
H2 H 0.0347 0.3565 0.6506 0.024 Uiso 1 1 calc R . .
C5 C 0.09999(7) 0.1166(3) 0.6273(3) 0.0215(4) Uani 1 1 d . . .
H3 H 0.0831 0.0299 0.7592 0.026 Uiso 1 1 calc R . .
O1 O 0.17980(5) -0.13475(18) 0.5545(3) 0.0290(3) Uani 1 1 d . . .
C6 C 0.18772(8) 0.5104(3) 0.0339(3) 0.0225(3) Uani 1 1 d . . .
H4 H 0.2245 0.4304 -0.0235 0.034 Uiso 1 1 calc R . .
H5 H 0.2009 0.6470 0.1088 0.034 Uiso 1 1 calc R . .
H6 H 0.1602 0.5380 -0.1119 0.034 Uiso 1 1 calc R . .
N2 N 0.06277(6) 0.6425(2) 0.3038(3) 0.0214(3) Uani 1 1 d . . .
O2 O 0.07545(6) 0.7368(2) 0.0994(3) 0.0346(4) Uani 1 1 d . . .
O3 O 0.02218(6) 0.7079(2) 0.4577(3) 0.0291(3) Uani 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
N1 0.0209(6) 0.0163(6) 0.0239(7) 0.0030(6) -0.0049(6) 0.0001(5)
C1 0.0173(7) 0.0203(7) 0.0219(7) -0.0001(6) -0.0004(6) -0.0008(6)
C2 0.0171(7) 0.0195(7) 0.0173(7) 0.0002(6) -0.0031(6) -0.0028(6)
C3 0.0177(7) 0.0164(7) 0.0190(7) 0.0006(6) -0.0041(6) -0.0006(6)
C4 0.0163(7) 0.0225(7) 0.0201(7) -0.0012(7) 0.0003(6) -0.0023(6)
C5 0.0213(7) 0.0215(7) 0.0217(7) 0.0040(7) -0.0008(6) -0.0050(6)
O1 0.0294(6) 0.0185(5) 0.0391(7) 0.0087(6) -0.0043(6) 0.0054(5)
C6 0.0218(7) 0.0255(8) 0.0201(7) 0.0051(7) 0.0018(7) -0.0015(6)
N2 0.0195(6) 0.0197(6) 0.0249(7) 0.0028(6) -0.0031(6) 0.0009(5)
O2 0.0313(7) 0.0359(7) 0.0364(7) 0.0195(6) 0.0025(6) 0.0083(6)
O3 0.0282(6) 0.0271(6) 0.0319(6) -0.0027(6) 0.0031(5) 0.0080(5)

_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
N1 O1 1.2972(16) . ?
N1 C1 1.360(2) . ?
N1 C5 1.365(2) . ?
C1 C2 1.390(2) . ?
C2 C3 1.401(2) . ?
C2 C6 1.500(2) . ?
C3 C4 1.391(2) . ?
C3 N2 1.4636(19) . ?
C4 C5 1.374(2) . ?
N2 O2 1.2264(18) . ?
N2 O3 1.2288(18) . ?

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
O1 N1 C1 119.95(14) . . ?
O1 N1 C5 119.85(14) . . ?
C1 N1 C5 120.21(13) . . ?
N1 C1 C2 122.93(14) . . ?
C1 C2 C3 115.84(14) . . ?
C1 C2 C6 117.36(14) . . ?
C3 C2 C6 126.73(14) . . ?
C4 C3 C2 121.46(14) . . ?
C4 C3 N2 116.57(13) . . ?
C2 C3 N2 121.96(13) . . ?
C5 C4 C3 119.67(15) . . ?
N1 C5 C4 119.85(14) . . ?
O2 N2 O3 123.24(14) . . ?
O2 N2 C3 118.43(14) . . ?
O3 N2 C3 118.32(13) . . ?

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
O1 N1 C1 C2 178.67(13) . . . . ?
C5 N1 C1 C2 -1.4(2) . . . . ?
N1 C1 C2 C3 -0.3(2) . . . . ?
N1 C1 C2 C6 176.78(14) . . . . ?
C1 C2 C3 C4 1.9(2) . . . . ?
C6 C2 C3 C4 -174.89(15) . . . . ?
C1 C2 C3 N2 -178.66(13) . . . . ?
C6 C2 C3 N2 4.5(2) . . . . ?
C2 C3 C4 C5 -1.8(2) . . . . ?
N2 C3 C4 C5 178.77(13) . . . . ?
O1 N1 C5 C4 -178.50(14) . . . . ?
C1 N1 C5 C4 1.6(2) . . . . ?
C3 C4 C5 N1 0.0(2) . . . . ?
C4 C3 N2 O2 -165.09(14) . . . . ?
C2 C3 N2 O2 15.5(2) . . . . ?
C4 C3 N2 O3 13.8(2) . . . . ?
C2 C3 N2 O3 -165.68(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.889
_diffrn_reflns_theta_full        28.91
_diffrn_measured_fraction_theta_full 0.889
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.035
_database_code_depnum_ccdc_archive 'CCDC 979898'
#######################################################################
#
#                 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_3-methyl-4-nitropyridine-N-oxide_150K

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-methyl-4-nitropyridine-N-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13

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           Orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   21.0223(8)
_cell_length_b                   6.1129(2)
_cell_length_c                   5.1343(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     659.79(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9629
_exptl_absorpt_correction_T_max  0.9750
_exptl_absorpt_process_details   '(CrysAlis Pro; Oxford Diffraction, 2010)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1853
_diffrn_reflns_av_R_equivalents  0.0123
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         3.47
_diffrn_reflns_theta_max         28.89
_reflns_number_total             933
_reflns_number_gt                873
_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          
; 
 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)+(0.0405P)²+0.0900P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.026(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_number_reflns         933
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0768
_refine_ls_wR_factor_gt          0.0754
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.127
_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
N1 N 0.15334(6) 0.0509(2) 0.4984(3) 0.0224(3) Uani 1 1 d . . .
C1 C 0.17908(7) 0.1802(3) 0.3095(3) 0.0216(3) Uani 1 1 d . . .
H1 H 0.2160 0.1334 0.2268 0.026 Uiso 1 1 calc R . .
C2 C 0.15256(7) 0.3787(3) 0.2351(3) 0.0192(3) Uani 1 1 d . . .
C3 C 0.09676(7) 0.4391(2) 0.3658(3) 0.0191(3) Uani 1 1 d . . .
C4 C 0.07134(7) 0.3102(2) 0.5627(3) 0.0211(3) Uani 1 1 d . . .
H2 H 0.0349 0.3552 0.6503 0.025 Uiso 1 1 calc R . .
C5 C 0.10015(7) 0.1161(3) 0.6277(3) 0.0231(4) Uani 1 1 d . . .
H3 H 0.0833 0.0295 0.7598 0.028 Uiso 1 1 calc R . .
O1 O 0.17994(5) -0.13488(19) 0.5556(3) 0.0319(3) Uani 1 1 d . . .
C6 C 0.18765(8) 0.5100(3) 0.0346(3) 0.0247(4) Uani 1 1 d . . .
H4 H 0.2244 0.4299 -0.0226 0.037 Uiso 1 1 calc R . .
H5 H 0.2008 0.6466 0.1093 0.037 Uiso 1 1 calc R . .
H6 H 0.1602 0.5374 -0.1112 0.037 Uiso 1 1 calc R . .
N2 N 0.06268(6) 0.6414(2) 0.3039(3) 0.0233(3) Uani 1 1 d . . .
O2 O 0.07537(6) 0.7356(2) 0.0996(3) 0.0379(4) Uani 1 1 d . . .
O3 O 0.02222(6) 0.7066(2) 0.4572(3) 0.0313(3) Uani 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
N1 0.0224(6) 0.0181(6) 0.0267(7) 0.0031(6) -0.0056(6) 0.0001(5)
C1 0.0196(7) 0.0217(7) 0.0236(7) 0.0002(7) -0.0002(6) -0.0004(6)
C2 0.0185(7) 0.0210(7) 0.0183(7) 0.0002(6) -0.0026(6) -0.0031(6)
C3 0.0195(7) 0.0182(7) 0.0196(7) 0.0008(6) -0.0041(6) -0.0006(6)
C4 0.0180(7) 0.0235(7) 0.0219(7) -0.0007(7) 0.0003(6) -0.0020(6)
C5 0.0229(7) 0.0235(8) 0.0229(7) 0.0044(7) -0.0010(6) -0.0057(6)
O1 0.0323(6) 0.0206(5) 0.0427(7) 0.0097(6) -0.0051(6) 0.0058(5)
C6 0.0241(7) 0.0275(8) 0.0224(7) 0.0055(7) 0.0026(7) -0.0014(6)
N2 0.0212(6) 0.0213(6) 0.0274(7) 0.0027(6) -0.0029(6) 0.0014(5)
O2 0.0342(7) 0.0395(7) 0.0399(7) 0.0218(7) 0.0031(6) 0.0092(6)
O3 0.0299(6) 0.0289(6) 0.0350(6) -0.0030(6) 0.0028(6) 0.0088(5)

_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
N1 O1 1.2997(16) . ?
N1 C5 1.360(2) . ?
N1 C1 1.363(2) . ?
C1 C2 1.389(2) . ?
C2 C3 1.401(2) . ?
C2 C6 1.499(2) . ?
C3 C4 1.389(2) . ?
C3 N2 1.464(2) . ?
C4 C5 1.373(2) . ?
N2 O2 1.2262(18) . ?
N2 O3 1.2257(18) . ?

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
O1 N1 C5 119.97(14) . . ?
O1 N1 C1 119.77(14) . . ?
C5 N1 C1 120.26(13) . . ?
N1 C1 C2 122.87(14) . . ?
C1 C2 C3 115.76(14) . . ?
C1 C2 C6 117.30(14) . . ?
C3 C2 C6 126.87(14) . . ?
C4 C3 C2 121.44(14) . . ?
C4 C3 N2 116.67(13) . . ?
C2 C3 N2 121.89(13) . . ?
C5 C4 C3 119.83(15) . . ?
N1 C5 C4 119.81(14) . . ?
O2 N2 O3 123.20(14) . . ?
O2 N2 C3 118.43(14) . . ?
O3 N2 C3 118.37(13) . . ?

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
O1 N1 C1 C2 178.80(14) . . . . ?
C5 N1 C1 C2 -1.4(2) . . . . ?
N1 C1 C2 C3 -0.4(2) . . . . ?
N1 C1 C2 C6 176.86(14) . . . . ?
C1 C2 C3 C4 2.0(2) . . . . ?
C6 C2 C3 C4 -174.97(15) . . . . ?
C1 C2 C3 N2 -178.55(13) . . . . ?
C6 C2 C3 N2 4.5(2) . . . . ?
C2 C3 C4 C5 -1.8(2) . . . . ?
N2 C3 C4 C5 178.76(13) . . . . ?
O1 N1 C5 C4 -178.52(14) . . . . ?
C1 N1 C5 C4 1.7(2) . . . . ?
C3 C4 C5 N1 -0.2(2) . . . . ?
C4 C3 N2 O2 -165.11(14) . . . . ?
C2 C3 N2 O2 15.4(2) . . . . ?
C4 C3 N2 O3 13.9(2) . . . . ?
C2 C3 N2 O3 -165.54(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.892
_diffrn_reflns_theta_full        28.89
_diffrn_measured_fraction_theta_full 0.892
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.036
_database_code_depnum_ccdc_archive 'CCDC 979899'
#######################################################################
#
#                 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_3-methyl-4-nitropyridine-N-oxide_165K

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-methyl-4-nitropyridine-N-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13

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           Orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   21.0588(8)
_cell_length_b                   6.1144(2)
_cell_length_c                   5.1343(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     661.10(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    165(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9630
_exptl_absorpt_correction_T_max  0.9751
_exptl_absorpt_process_details   '(CrysAlis Pro; Oxford Diffraction, 2010)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      165(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  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1857
_diffrn_reflns_av_R_equivalents  0.0122
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.47
_diffrn_reflns_theta_max         28.86
_reflns_number_total             935
_reflns_number_gt                870
_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          
; 
 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)+(0.0393P)²+0.1072P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.027(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_number_reflns         935
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0775
_refine_ls_wR_factor_gt          0.0748
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_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
N1 N 0.15347(6) 0.0509(2) 0.4992(3) 0.0239(3) Uani 1 1 d . . .
C1 C 0.17902(7) 0.1799(3) 0.3104(3) 0.0233(4) Uani 1 1 d . . .
H1 H 0.2159 0.1331 0.2275 0.028 Uiso 1 1 calc R . .
C2 C 0.15255(7) 0.3784(3) 0.2359(3) 0.0209(3) Uani 1 1 d . . .
C3 C 0.09676(7) 0.4384(3) 0.3660(3) 0.0203(3) Uani 1 1 d . . .
C4 C 0.07134(7) 0.3096(3) 0.5630(3) 0.0229(3) Uani 1 1 d . . .
H2 H 0.0349 0.3545 0.6504 0.028 Uiso 1 1 calc R . .
C5 C 0.10018(8) 0.1155(3) 0.6282(3) 0.0251(4) Uani 1 1 d . . .
H3 H 0.0834 0.0287 0.7600 0.030 Uiso 1 1 calc R . .
O1 O 0.18003(6) -0.1348(2) 0.5568(3) 0.0346(3) Uani 1 1 d . . .
C6 C 0.18749(8) 0.5094(3) 0.0356(3) 0.0267(4) Uani 1 1 d . . .
H4 H 0.2242 0.4296 -0.0216 0.040 Uiso 1 1 calc R . .
H5 H 0.2006 0.6461 0.1102 0.040 Uiso 1 1 calc R . .
H6 H 0.1601 0.5367 -0.1103 0.040 Uiso 1 1 calc R . .
N2 N 0.06265(6) 0.6402(2) 0.3041(3) 0.0253(3) Uani 1 1 d . . .
O2 O 0.07529(6) 0.7343(2) 0.0999(3) 0.0412(4) Uani 1 1 d . . .
O3 O 0.02227(6) 0.7053(2) 0.4572(3) 0.0344(3) Uani 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
N1 0.0240(6) 0.0190(6) 0.0287(7) 0.0036(6) -0.0061(6) -0.0003(5)
C1 0.0205(7) 0.0239(8) 0.0254(8) 0.0007(7) -0.0006(6) -0.0004(6)
C2 0.0206(7) 0.0225(7) 0.0196(7) 0.0009(7) -0.0027(6) -0.0035(6)
C3 0.0205(7) 0.0193(7) 0.0211(7) 0.0009(7) -0.0039(6) -0.0003(6)
C4 0.0201(7) 0.0251(7) 0.0237(7) -0.0007(7) 0.0010(7) -0.0025(6)
C5 0.0250(8) 0.0252(8) 0.0251(8) 0.0052(7) -0.0009(7) -0.0058(7)
O1 0.0350(6) 0.0229(6) 0.0458(8) 0.0102(6) -0.0050(6) 0.0064(5)
C6 0.0258(7) 0.0298(8) 0.0246(8) 0.0056(8) 0.0030(7) -0.0016(7)
N2 0.0233(6) 0.0226(6) 0.0300(7) 0.0027(6) -0.0035(6) 0.0014(6)
O2 0.0375(7) 0.0428(8) 0.0434(8) 0.0239(7) 0.0037(7) 0.0108(6)
O3 0.0331(6) 0.0316(6) 0.0385(7) -0.0033(7) 0.0035(6) 0.0101(5)

_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
N1 O1 1.2998(17) . ?
N1 C1 1.360(2) . ?
N1 C5 1.362(2) . ?
C1 C2 1.389(2) . ?
C2 C3 1.401(2) . ?
C2 C6 1.497(2) . ?
C3 C4 1.389(2) . ?
C3 N2 1.463(2) . ?
C4 C5 1.374(2) . ?
N2 O2 1.2250(19) . ?
N2 O3 1.2243(18) . ?

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
O1 N1 C1 119.90(14) . . ?
O1 N1 C5 119.82(14) . . ?
C1 N1 C5 120.29(13) . . ?
N1 C1 C2 122.96(15) . . ?
C1 C2 C3 115.71(14) . . ?
C1 C2 C6 117.37(14) . . ?
C3 C2 C6 126.87(15) . . ?
C4 C3 C2 121.48(14) . . ?
C4 C3 N2 116.58(14) . . ?
C2 C3 N2 121.94(14) . . ?
C5 C4 C3 119.79(15) . . ?
N1 C5 C4 119.73(15) . . ?
O2 N2 O3 123.22(15) . . ?
O2 N2 C3 118.38(14) . . ?
O3 N2 C3 118.39(14) . . ?

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
O1 N1 C1 C2 178.89(14) . . . . ?
C5 N1 C1 C2 -1.1(2) . . . . ?
N1 C1 C2 C3 -0.7(2) . . . . ?
N1 C1 C2 C6 176.79(14) . . . . ?
C1 C2 C3 C4 2.2(2) . . . . ?
C6 C2 C3 C4 -175.03(15) . . . . ?
C1 C2 C3 N2 -178.50(14) . . . . ?
C6 C2 C3 N2 4.3(2) . . . . ?
C2 C3 C4 C5 -1.9(2) . . . . ?
N2 C3 C4 C5 178.76(13) . . . . ?
O1 N1 C5 C4 -178.53(14) . . . . ?
C1 N1 C5 C4 1.5(2) . . . . ?
C3 C4 C5 N1 0.0(2) . . . . ?
C4 C3 N2 O2 -165.06(15) . . . . ?
C2 C3 N2 O2 15.6(2) . . . . ?
C4 C3 N2 O3 14.0(2) . . . . ?
C2 C3 N2 O3 -165.42(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.894
_diffrn_reflns_theta_full        28.86
_diffrn_measured_fraction_theta_full 0.894
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.035
_database_code_depnum_ccdc_archive 'CCDC 979900'
#######################################################################
#
#                 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_3-methyl-4-nitropyridine-N-oxide_180K

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-methyl-4-nitropyridine-N-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13

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           Orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   21.0975(9)
_cell_length_b                   6.1157(3)
_cell_length_c                   5.1353(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     662.59(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9631
_exptl_absorpt_correction_T_max  0.9752
_exptl_absorpt_process_details   '(CrysAlis Pro; Oxford Diffraction, 2010)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      180(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  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1856
_diffrn_reflns_av_R_equivalents  0.0114
_diffrn_reflns_av_sigmaI/netI    0.0164
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         3.47
_diffrn_reflns_theta_max         28.84
_reflns_number_total             938
_reflns_number_gt                881
_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          
; 
 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)+(0.0374P)²+0.1334P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.031(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_number_reflns         938
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0794
_refine_ls_wR_factor_gt          0.0767
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_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
N1 N 0.15352(7) 0.0506(2) 0.5002(3) 0.0260(3) Uani 1 1 d . . .
C1 C 0.17916(8) 0.1794(3) 0.3120(3) 0.0251(4) Uani 1 1 d . . .
H1 H 0.2161 0.1331 0.2301 0.030 Uiso 1 1 calc R . .
C2 C 0.15255(7) 0.3777(3) 0.2368(3) 0.0222(4) Uani 1 1 d . . .
C3 C 0.09681(7) 0.4375(3) 0.3667(3) 0.0222(4) Uani 1 1 d . . .
C4 C 0.07141(8) 0.3087(3) 0.5630(3) 0.0250(4) Uani 1 1 d . . .
H2 H 0.0350 0.3533 0.6500 0.030 Uiso 1 1 calc R . .
C5 C 0.10022(8) 0.1149(3) 0.6285(4) 0.0274(4) Uani 1 1 d . . .
H3 H 0.0834 0.0280 0.7600 0.033 Uiso 1 1 calc R . .
O1 O 0.18008(6) -0.1346(2) 0.5579(3) 0.0379(4) Uani 1 1 d . . .
C6 C 0.18741(8) 0.5090(3) 0.0364(3) 0.0287(4) Uani 1 1 d . . .
H4 H 0.2240 0.4293 -0.0209 0.043 Uiso 1 1 calc R . .
H5 H 0.2005 0.6457 0.1110 0.043 Uiso 1 1 calc R . .
H6 H 0.1600 0.5362 -0.1094 0.043 Uiso 1 1 calc R . .
N2 N 0.06272(7) 0.6393(2) 0.3041(3) 0.0276(3) Uani 1 1 d . . .
O2 O 0.07528(7) 0.7335(2) 0.1002(3) 0.0452(4) Uani 1 1 d . . .
O3 O 0.02226(6) 0.7041(2) 0.4570(3) 0.0374(4) Uani 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
N1 0.0263(7) 0.0205(6) 0.0313(7) 0.0046(7) -0.0065(6) -0.0002(5)
C1 0.0219(8) 0.0258(8) 0.0275(8) 0.0006(7) -0.0001(7) 0.0003(6)
C2 0.0218(7) 0.0235(8) 0.0213(8) 0.0013(7) -0.0026(7) -0.0027(6)
C3 0.0214(7) 0.0214(7) 0.0237(8) 0.0008(7) -0.0040(6) -0.0008(6)
C4 0.0223(7) 0.0277(8) 0.0249(8) -0.0001(8) 0.0011(7) -0.0021(6)
C5 0.0270(8) 0.0275(8) 0.0276(8) 0.0051(8) -0.0008(7) -0.0065(7)
O1 0.0382(7) 0.0251(6) 0.0504(9) 0.0116(7) -0.0053(7) 0.0073(5)
C6 0.0275(8) 0.0317(9) 0.0267(8) 0.0059(8) 0.0034(7) -0.0014(7)
N2 0.0250(7) 0.0245(7) 0.0333(8) 0.0028(6) -0.0038(6) 0.0018(6)
O2 0.0411(8) 0.0470(8) 0.0473(8) 0.0255(8) 0.0034(7) 0.0120(7)
O3 0.0354(7) 0.0340(7) 0.0427(8) -0.0026(7) 0.0039(6) 0.0107(5)

_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
N1 O1 1.2979(18) . ?
N1 C1 1.359(2) . ?
N1 C5 1.361(2) . ?
C1 C2 1.391(2) . ?
C2 C3 1.401(2) . ?
C2 C6 1.498(2) . ?
C3 C4 1.387(2) . ?
C3 N2 1.464(2) . ?
C4 C5 1.374(2) . ?
N2 O2 1.224(2) . ?
N2 O3 1.2258(19) . ?

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
O1 N1 C1 119.77(15) . . ?
O1 N1 C5 119.89(15) . . ?
C1 N1 C5 120.34(14) . . ?
N1 C1 C2 122.84(15) . . ?
C1 C2 C3 115.74(15) . . ?
C1 C2 C6 117.39(15) . . ?
C3 C2 C6 126.81(15) . . ?
C4 C3 C2 121.48(15) . . ?
C4 C3 N2 116.67(14) . . ?
C2 C3 N2 121.85(15) . . ?
C5 C4 C3 119.80(16) . . ?
N1 C5 C4 119.76(16) . . ?
O2 N2 O3 123.13(16) . . ?
O2 N2 C3 118.60(15) . . ?
O3 N2 C3 118.27(15) . . ?

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
O1 N1 C1 C2 178.70(15) . . . . ?
C5 N1 C1 C2 -1.4(3) . . . . ?
N1 C1 C2 C3 -0.3(2) . . . . ?
N1 C1 C2 C6 176.98(15) . . . . ?
C1 C2 C3 C4 1.8(2) . . . . ?
C6 C2 C3 C4 -175.17(16) . . . . ?
C1 C2 C3 N2 -178.61(15) . . . . ?
C6 C2 C3 N2 4.4(3) . . . . ?
C2 C3 C4 C5 -1.7(2) . . . . ?
N2 C3 C4 C5 178.72(14) . . . . ?
O1 N1 C5 C4 -178.53(15) . . . . ?
C1 N1 C5 C4 1.5(2) . . . . ?
C3 C4 C5 N1 0.0(2) . . . . ?
C4 C3 N2 O2 -164.96(16) . . . . ?
C2 C3 N2 O2 15.5(2) . . . . ?
C4 C3 N2 O3 14.0(2) . . . . ?
C2 C3 N2 O3 -165.54(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.897
_diffrn_reflns_theta_full        28.84
_diffrn_measured_fraction_theta_full 0.897
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.035
_database_code_depnum_ccdc_archive 'CCDC 979901'
#######################################################################
#
#                 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_3-methyl-4-nitropyridine-N-oxide_195K

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-methyl-4-nitropyridine-N-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13

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           Orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   21.1324(8)
_cell_length_b                   6.1162(2)
_cell_length_c                   5.1363(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     663.87(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    195(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9631
_exptl_absorpt_correction_T_max  0.9752
_exptl_absorpt_process_details   '(CrysAlis Pro; Oxford Diffraction, 2010)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      195(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            1866
_diffrn_reflns_av_R_equivalents  0.0123
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         3.47
_diffrn_reflns_theta_max         28.81
_reflns_number_total             939
_reflns_number_gt                876
_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          
; 
 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)+(0.0400P)²+0.0933P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.031(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_number_reflns         939
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0832
_refine_ls_wR_factor_gt          0.0790
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_restrained_S_all      1.155
_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
N1 N 0.15366(7) 0.0503(2) 0.5009(3) 0.0280(3) Uani 1 1 d . . .
C1 C 0.17908(8) 0.1794(3) 0.3127(4) 0.0267(4) Uani 1 1 d . . .
H1 H 0.2159 0.1332 0.2303 0.032 Uiso 1 1 calc R . .
C2 C 0.15250(7) 0.3771(3) 0.2379(3) 0.0243(4) Uani 1 1 d . . .
C3 C 0.09676(7) 0.4367(3) 0.3670(3) 0.0235(4) Uani 1 1 d . . .
C4 C 0.07144(8) 0.3075(3) 0.5631(3) 0.0269(4) Uani 1 1 d . . .
H2 H 0.0350 0.3517 0.6496 0.032 Uiso 1 1 calc R . .
C5 C 0.10035(8) 0.1146(3) 0.6291(4) 0.0296(4) Uani 1 1 d . . .
H3 H 0.0836 0.0279 0.7609 0.035 Uiso 1 1 calc R . .
O1 O 0.18032(6) -0.1345(2) 0.5591(3) 0.0409(4) Uani 1 1 d . . .
C6 C 0.18732(8) 0.5086(3) 0.0373(3) 0.0310(4) Uani 1 1 d . . .
H4 H 0.2239 0.4290 -0.0199 0.046 Uiso 1 1 calc R . .
H5 H 0.2003 0.6453 0.1118 0.046 Uiso 1 1 calc R . .
H6 H 0.1600 0.5356 -0.1086 0.046 Uiso 1 1 calc R . .
N2 N 0.06273(7) 0.6379(3) 0.3041(3) 0.0293(4) Uani 1 1 d . . .
O2 O 0.07520(7) 0.7318(2) 0.1003(3) 0.0486(4) Uani 1 1 d . . .
O3 O 0.02236(6) 0.7026(2) 0.4567(3) 0.0403(4) Uani 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
N1 0.0275(7) 0.0225(7) 0.0341(8) 0.0045(7) -0.0063(6) -0.0005(5)
C1 0.0234(8) 0.0265(8) 0.0303(8) 0.0004(8) 0.0003(7) 0.0005(7)
C2 0.0231(8) 0.0259(8) 0.0239(8) 0.0009(7) -0.0034(7) -0.0027(6)
C3 0.0231(7) 0.0224(7) 0.0250(8) 0.0006(7) -0.0044(7) 0.0000(6)
C4 0.0242(8) 0.0294(8) 0.0271(8) 0.0003(8) 0.0010(7) -0.0035(7)
C5 0.0295(8) 0.0298(9) 0.0295(9) 0.0071(8) -0.0010(7) -0.0062(7)
O1 0.0405(7) 0.0267(6) 0.0556(9) 0.0124(7) -0.0064(7) 0.0077(6)
C6 0.0294(8) 0.0342(9) 0.0293(8) 0.0077(8) 0.0044(7) -0.0014(7)
N2 0.0265(7) 0.0272(7) 0.0342(8) 0.0033(7) -0.0034(6) 0.0018(6)
O2 0.0441(8) 0.0505(9) 0.0511(9) 0.0273(8) 0.0046(7) 0.0138(7)
O3 0.0384(7) 0.0367(7) 0.0457(8) -0.0028(7) 0.0038(7) 0.0124(6)

_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
N1 O1 1.2980(18) . ?
N1 C1 1.359(2) . ?
N1 C5 1.363(2) . ?
C1 C2 1.388(2) . ?
C2 C3 1.400(2) . ?
C2 C6 1.500(2) . ?
C3 C4 1.387(2) . ?
C3 N2 1.462(2) . ?
C4 C5 1.371(2) . ?
N2 O2 1.222(2) . ?
N2 O3 1.2244(19) . ?

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
O1 N1 C1 119.89(15) . . ?
O1 N1 C5 119.93(15) . . ?
C1 N1 C5 120.18(14) . . ?
N1 C1 C2 122.90(16) . . ?
C1 C2 C3 115.87(16) . . ?
C1 C2 C6 117.30(15) . . ?
C3 C2 C6 126.78(15) . . ?
C4 C3 C2 121.35(15) . . ?
C4 C3 N2 116.77(15) . . ?
C2 C3 N2 121.88(15) . . ?
C5 C4 C3 119.84(16) . . ?
N1 C5 C4 119.82(16) . . ?
O2 N2 O3 123.13(16) . . ?
O2 N2 C3 118.62(16) . . ?
O3 N2 C3 118.25(14) . . ?

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
O1 N1 C1 C2 178.96(15) . . . . ?
C5 N1 C1 C2 -1.2(3) . . . . ?
N1 C1 C2 C3 -0.7(2) . . . . ?
N1 C1 C2 C6 176.92(15) . . . . ?
C1 C2 C3 C4 2.0(2) . . . . ?
C6 C2 C3 C4 -175.27(16) . . . . ?
C1 C2 C3 N2 -178.51(15) . . . . ?
C6 C2 C3 N2 4.2(3) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
N2 C3 C4 C5 178.90(14) . . . . ?
O1 N1 C5 C4 -178.48(15) . . . . ?
C1 N1 C5 C4 1.7(3) . . . . ?
C3 C4 C5 N1 -0.3(3) . . . . ?
C4 C3 N2 O2 -164.81(16) . . . . ?
C2 C3 N2 O2 15.7(2) . . . . ?
C4 C3 N2 O3 14.1(2) . . . . ?
C2 C3 N2 O3 -165.35(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.900
_diffrn_reflns_theta_full        28.81
_diffrn_measured_fraction_theta_full 0.900
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.035
_database_code_depnum_ccdc_archive 'CCDC 979902'
#######################################################################
#
#                 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_3-methyl-4-nitropyridine-N-oxide_210K

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-methyl-4-nitropyridine-N-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13

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           Orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   21.1719(9)
_cell_length_b                   6.1190(3)
_cell_length_c                   5.1373(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     665.54(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9632
_exptl_absorpt_correction_T_max  0.9753
_exptl_absorpt_process_details   '(CrysAlis Pro; Oxford Diffraction, 2010)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      210(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  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1869
_diffrn_reflns_av_R_equivalents  0.0119
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         3.47
_diffrn_reflns_theta_max         28.78
_reflns_number_total             940
_reflns_number_gt                866
_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          
; 
 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)+(0.0422P)²+0.0805P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.029(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_number_reflns         940
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0845
_refine_ls_wR_factor_gt          0.0811
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_restrained_S_all      1.152
_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
N1 N 0.15375(7) 0.0502(2) 0.5019(3) 0.0302(4) Uani 1 1 d . . .
C1 C 0.17901(8) 0.1794(3) 0.3141(4) 0.0289(4) Uani 1 1 d . . .
H1 H 0.2159 0.1335 0.2322 0.035 Uiso 1 1 calc R . .
C2 C 0.15251(7) 0.3766(3) 0.2386(3) 0.0256(4) Uani 1 1 d . . .
C3 C 0.09683(8) 0.4356(3) 0.3675(3) 0.0250(4) Uani 1 1 d . . .
C4 C 0.07154(8) 0.3068(3) 0.5636(3) 0.0288(4) Uani 1 1 d . . .
H2 H 0.0351 0.3511 0.6501 0.035 Uiso 1 1 calc R . .
C5 C 0.10036(8) 0.1140(3) 0.6295(4) 0.0313(4) Uani 1 1 d . . .
H3 H 0.0836 0.0270 0.7609 0.038 Uiso 1 1 calc R . .
O1 O 0.18034(6) -0.1347(2) 0.5605(3) 0.0437(4) Uani 1 1 d . . .
C6 C 0.18724(9) 0.5079(3) 0.0380(4) 0.0334(4) Uani 1 1 d . . .
H4 H 0.2238 0.4283 -0.0190 0.050 Uiso 1 1 calc R . .
H5 H 0.2002 0.6446 0.1124 0.050 Uiso 1 1 calc R . .
H6 H 0.1600 0.5347 -0.1079 0.050 Uiso 1 1 calc R . .
N2 N 0.06266(7) 0.6367(3) 0.3043(3) 0.0316(4) Uani 1 1 d . . .
O2 O 0.07517(7) 0.7306(3) 0.1007(3) 0.0523(5) Uani 1 1 d . . .
O3 O 0.02239(7) 0.7014(2) 0.4566(3) 0.0435(4) Uani 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
N1 0.0291(7) 0.0240(7) 0.0374(8) 0.0052(7) -0.0074(7) -0.0001(5)
C1 0.0252(8) 0.0289(8) 0.0327(8) 0.0018(8) -0.0007(7) 0.0007(7)
C2 0.0240(8) 0.0277(8) 0.0249(8) 0.0004(7) -0.0033(7) -0.0031(7)
C3 0.0235(8) 0.0245(7) 0.0270(8) 0.0013(7) -0.0042(7) -0.0005(6)
C4 0.0252(8) 0.0315(8) 0.0298(8) -0.0003(8) 0.0020(7) -0.0038(7)
C5 0.0303(8) 0.0315(9) 0.0321(9) 0.0069(8) -0.0010(7) -0.0074(7)
O1 0.0440(7) 0.0285(6) 0.0587(9) 0.0135(7) -0.0066(8) 0.0081(6)
C6 0.0314(8) 0.0372(9) 0.0316(9) 0.0070(9) 0.0043(8) -0.0019(8)
N2 0.0276(7) 0.0292(7) 0.0379(8) 0.0040(7) -0.0036(7) 0.0017(6)
O2 0.0473(8) 0.0547(9) 0.0548(9) 0.0303(8) 0.0045(8) 0.0146(7)
O3 0.0409(7) 0.0404(7) 0.0492(8) -0.0033(8) 0.0043(7) 0.0130(6)

_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
N1 O1 1.2988(18) . ?
N1 C1 1.357(2) . ?
N1 C5 1.364(2) . ?
C1 C2 1.386(2) . ?
C2 C3 1.399(2) . ?
C2 C6 1.499(2) . ?
C3 C4 1.386(2) . ?
C3 N2 1.464(2) . ?
C4 C5 1.371(2) . ?
N2 O2 1.222(2) . ?
N2 O3 1.2231(19) . ?

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
O1 N1 C1 120.09(16) . . ?
O1 N1 C5 119.81(16) . . ?
C1 N1 C5 120.09(14) . . ?
N1 C1 C2 123.14(16) . . ?
C1 C2 C3 115.68(15) . . ?
C1 C2 C6 117.39(15) . . ?
C3 C2 C6 126.88(16) . . ?
C4 C3 C2 121.49(15) . . ?
C4 C3 N2 116.62(15) . . ?
C2 C3 N2 121.89(15) . . ?
C5 C4 C3 119.80(17) . . ?
N1 C5 C4 119.76(16) . . ?
O2 N2 O3 123.13(16) . . ?
O2 N2 C3 118.53(16) . . ?
O3 N2 C3 118.33(15) . . ?

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
O1 N1 C1 C2 178.82(15) . . . . ?
C5 N1 C1 C2 -1.1(3) . . . . ?
N1 C1 C2 C3 -0.6(3) . . . . ?
N1 C1 C2 C6 177.01(15) . . . . ?
C1 C2 C3 C4 2.0(2) . . . . ?
C6 C2 C3 C4 -175.28(17) . . . . ?
C1 C2 C3 N2 -178.54(15) . . . . ?
C6 C2 C3 N2 4.1(3) . . . . ?
C2 C3 C4 C5 -1.8(3) . . . . ?
N2 C3 C4 C5 178.73(14) . . . . ?
O1 N1 C5 C4 -178.55(16) . . . . ?
C1 N1 C5 C4 1.4(3) . . . . ?
C3 C4 C5 N1 0.0(3) . . . . ?
C4 C3 N2 O2 -164.93(16) . . . . ?
C2 C3 N2 O2 15.6(2) . . . . ?
C4 C3 N2 O3 14.2(2) . . . . ?
C2 C3 N2 O3 -165.24(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.901
_diffrn_reflns_theta_full        28.78
_diffrn_measured_fraction_theta_full 0.901
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.035
_database_code_depnum_ccdc_archive 'CCDC 979903'
#######################################################################
#
#                 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_3-methyl-4-nitropyridine-N-oxide_225K

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-methyl-4-nitropyridine-N-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13

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           Orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   21.2160(9)
_cell_length_b                   6.1203(3)
_cell_length_c                   5.1381(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     667.17(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    225(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?


_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9633
_exptl_absorpt_correction_T_max  0.9753
_exptl_absorpt_process_details   '(CrysAlis Pro; Oxford Diffraction, 2010)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      225(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  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1876
_diffrn_reflns_av_R_equivalents  0.0125
_diffrn_reflns_av_sigmaI/netI    0.0174
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         3.46
_diffrn_reflns_theta_max         28.75
_reflns_number_total             941
_reflns_number_gt                868
_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          
; 
 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)+(0.0364P)²+0.0948P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.032(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_number_reflns         941
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0828
_refine_ls_wR_factor_gt          0.0796
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_restrained_S_all      1.173
_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
N1 N 0.15385(7) 0.0498(2) 0.5030(3) 0.0325(4) Uani 1 1 d . . .
C1 C 0.17902(8) 0.1794(3) 0.3154(4) 0.0310(4) Uani 1 1 d . . .
H1 H 0.2159 0.1338 0.2337 0.037 Uiso 1 1 calc R . .
C2 C 0.15253(8) 0.3759(3) 0.2398(3) 0.0271(4) Uani 1 1 d . . .
C3 C 0.09687(8) 0.4349(3) 0.3680(3) 0.0266(4) Uani 1 1 d . . .
C4 C 0.07154(8) 0.3055(3) 0.5633(4) 0.0311(4) Uani 1 1 d . . .
H2 H 0.0350 0.3492 0.6489 0.037 Uiso 1 1 calc R . .
C5 C 0.10045(9) 0.1131(3) 0.6301(4) 0.0338(4) Uani 1 1 d . . .
H3 H 0.0837 0.0261 0.7614 0.041 Uiso 1 1 calc R . .
O1 O 0.18046(7) -0.1344(2) 0.5621(3) 0.0474(4) Uani 1 1 d . . .
C6 C 0.18714(9) 0.5075(3) 0.0392(4) 0.0361(4) Uani 1 1 d . . .
H4 H 0.2236 0.4282 -0.0178 0.054 Uiso 1 1 calc R . .
H5 H 0.2000 0.6443 0.1138 0.054 Uiso 1 1 calc R . .
H6 H 0.1599 0.5343 -0.1066 0.054 Uiso 1 1 calc R . .
N2 N 0.06264(7) 0.6356(3) 0.3047(3) 0.0345(4) Uani 1 1 d . . .
O2 O 0.07504(8) 0.7294(3) 0.1009(3) 0.0567(5) Uani 1 1 d . . .
O3 O 0.02238(7) 0.6998(2) 0.4566(3) 0.0466(4) Uani 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
N1 0.0327(7) 0.0254(7) 0.0393(8) 0.0062(7) -0.0071(7) 0.0003(6)
C1 0.0269(8) 0.0313(9) 0.0347(9) 0.0006(8) -0.0008(8) 0.0017(7)
C2 0.0268(8) 0.0298(8) 0.0246(8) 0.0021(7) -0.0032(7) -0.0031(7)
C3 0.0250(8) 0.0265(8) 0.0285(8) 0.0005(7) -0.0042(7) -0.0002(6)
C4 0.0277(8) 0.0330(8) 0.0327(9) 0.0001(8) 0.0019(8) -0.0036(7)
C5 0.0347(9) 0.0339(9) 0.0329(9) 0.0068(8) -0.0015(8) -0.0082(8)
O1 0.0473(8) 0.0318(7) 0.0632(10) 0.0145(8) -0.0065(8) 0.0091(6)
C6 0.0339(9) 0.0408(9) 0.0336(9) 0.0079(9) 0.0054(8) -0.0013(8)
N2 0.0301(7) 0.0316(8) 0.0416(9) 0.0036(7) -0.0039(7) 0.0026(7)
O2 0.0508(9) 0.0600(10) 0.0592(9) 0.0327(9) 0.0052(8) 0.0164(8)
O3 0.0430(8) 0.0432(8) 0.0537(9) -0.0036(8) 0.0048(7) 0.0135(6)

_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
N1 O1 1.2968(18) . ?
N1 C1 1.358(2) . ?
N1 C5 1.364(2) . ?
C1 C2 1.384(2) . ?
C2 C3 1.400(2) . ?
C2 C6 1.500(2) . ?
C3 C4 1.387(2) . ?
C3 N2 1.464(2) . ?
C4 C5 1.371(3) . ?
N2 O3 1.222(2) . ?
N2 O2 1.223(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
O1 N1 C1 120.19(16) . . ?
O1 N1 C5 119.76(16) . . ?
C1 N1 C5 120.05(15) . . ?
N1 C1 C2 123.19(16) . . ?
C1 C2 C3 115.77(16) . . ?
C1 C2 C6 117.45(16) . . ?
C3 C2 C6 126.73(16) . . ?
C4 C3 C2 121.37(16) . . ?
C4 C3 N2 116.60(15) . . ?
C2 C3 N2 122.03(15) . . ?
C5 C4 C3 119.87(17) . . ?
N1 C5 C4 119.71(17) . . ?
O3 N2 O2 123.11(17) . . ?
O3 N2 C3 118.34(15) . . ?
O2 N2 C3 118.54(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
O1 N1 C1 C2 178.92(16) . . . . ?
C5 N1 C1 C2 -1.1(3) . . . . ?
N1 C1 C2 C3 -0.5(3) . . . . ?
N1 C1 C2 C6 177.06(16) . . . . ?
C1 C2 C3 C4 1.8(2) . . . . ?
C6 C2 C3 C4 -175.53(17) . . . . ?
C1 C2 C3 N2 -178.54(15) . . . . ?
C6 C2 C3 N2 4.2(3) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
N2 C3 C4 C5 178.87(15) . . . . ?
O1 N1 C5 C4 -178.54(16) . . . . ?
C1 N1 C5 C4 1.5(3) . . . . ?
C3 C4 C5 N1 -0.3(3) . . . . ?
C4 C3 N2 O3 14.4(2) . . . . ?
C2 C3 N2 O3 -165.27(16) . . . . ?
C4 C3 N2 O2 -164.59(17) . . . . ?
C2 C3 N2 O2 15.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.902
_diffrn_reflns_theta_full        28.75
_diffrn_measured_fraction_theta_full 0.902
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.034
_database_code_depnum_ccdc_archive 'CCDC 979904'
#######################################################################
#
#                 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_3-methyl-4-nitropyridine-N-oxide_240K

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-methyl-4-nitropyridine-N-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13

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           Orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   21.2598(9)
_cell_length_b                   6.1219(3)
_cell_length_c                   5.1391(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     668.86(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    240(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9634
_exptl_absorpt_correction_T_max  0.9754
_exptl_absorpt_process_details   '(CrysAlis Pro; Oxford Diffraction, 2010)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      240(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  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1876
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.46
_diffrn_reflns_theta_max         28.72
_reflns_number_total             944
_reflns_number_gt                859
_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          
; 
 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)+(0.0422P)²+0.0623P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.034(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_number_reflns         944
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0859
_refine_ls_wR_factor_gt          0.0804
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_restrained_S_all      1.130
_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
N1 N 0.15386(7) 0.0495(2) 0.5040(3) 0.0347(4) Uani 1 1 d . . .
C1 C 0.17903(8) 0.1787(3) 0.3165(4) 0.0330(4) Uani 1 1 d . . .
H1 H 0.2158 0.1331 0.2351 0.040 Uiso 1 1 calc R . .
C2 C 0.15246(8) 0.3754(3) 0.2407(3) 0.0289(4) Uani 1 1 d . . .
C3 C 0.09686(8) 0.4339(3) 0.3687(3) 0.0285(4) Uani 1 1 d . . .
C4 C 0.07166(8) 0.3045(3) 0.5632(3) 0.0332(4) Uani 1 1 d . . .
H2 H 0.0351 0.3479 0.6484 0.040 Uiso 1 1 calc R . .
C5 C 0.10048(9) 0.1128(3) 0.6304(4) 0.0365(4) Uani 1 1 d . . .
H3 H 0.0837 0.0260 0.7617 0.044 Uiso 1 1 calc R . .
O1 O 0.18059(7) -0.1345(2) 0.5635(3) 0.0511(4) Uani 1 1 d . . .
C6 C 0.18704(9) 0.5065(3) 0.0404(4) 0.0387(4) Uani 1 1 d . . .
H4 H 0.2235 0.4270 -0.0163 0.058 Uiso 1 1 calc R . .
H5 H 0.1999 0.6432 0.1148 0.058 Uiso 1 1 calc R . .
H6 H 0.1599 0.5331 -0.1055 0.058 Uiso 1 1 calc R . .
N2 N 0.06259(7) 0.6342(3) 0.3052(3) 0.0367(4) Uani 1 1 d . . .
O2 O 0.07500(8) 0.7279(3) 0.1014(3) 0.0606(5) Uani 1 1 d . . .
O3 O 0.02244(7) 0.6986(2) 0.4566(3) 0.0509(4) Uani 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
N1 0.0353(8) 0.0274(7) 0.0415(8) 0.0063(7) -0.0070(7) 0.0002(6)
C1 0.0292(8) 0.0321(9) 0.0377(9) 0.0005(8) 0.0003(8) 0.0014(7)
C2 0.0286(8) 0.0302(8) 0.0280(8) 0.0020(7) -0.0034(7) -0.0036(7)
C3 0.0271(8) 0.0279(8) 0.0307(8) 0.0012(7) -0.0043(7) -0.0002(6)
C4 0.0302(8) 0.0355(8) 0.0340(9) 0.0013(8) 0.0017(8) -0.0037(7)
C5 0.0373(9) 0.0366(9) 0.0357(10) 0.0083(8) -0.0011(8) -0.0078(8)
O1 0.0512(8) 0.0340(7) 0.0682(10) 0.0165(8) -0.0073(8) 0.0101(6)
C6 0.0366(9) 0.0429(10) 0.0367(9) 0.0080(9) 0.0054(8) -0.0024(8)
N2 0.0332(8) 0.0336(8) 0.0433(9) 0.0039(7) -0.0040(7) 0.0024(7)
O2 0.0554(9) 0.0635(10) 0.0630(9) 0.0352(9) 0.0057(8) 0.0175(8)
O3 0.0479(8) 0.0466(8) 0.0583(9) -0.0031(9) 0.0068(8) 0.0158(6)

_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
N1 O1 1.2984(18) . ?
N1 C1 1.356(2) . ?
N1 C5 1.364(2) . ?
C1 C2 1.386(2) . ?
C2 C3 1.399(2) . ?
C2 C6 1.498(2) . ?
C3 C4 1.383(2) . ?
C3 N2 1.463(2) . ?
C4 C5 1.368(3) . ?
N2 O3 1.220(2) . ?
N2 O2 1.223(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
O1 N1 C1 120.03(16) . . ?
O1 N1 C5 119.90(16) . . ?
C1 N1 C5 120.07(15) . . ?
N1 C1 C2 123.06(16) . . ?
C1 C2 C3 115.72(16) . . ?
C1 C2 C6 117.30(16) . . ?
C3 C2 C6 126.93(16) . . ?
C4 C3 C2 121.37(16) . . ?
C4 C3 N2 116.62(15) . . ?
C2 C3 N2 122.01(15) . . ?
C5 C4 C3 120.00(17) . . ?
N1 C5 C4 119.74(16) . . ?
O3 N2 O2 123.04(17) . . ?
O3 N2 C3 118.50(15) . . ?
O2 N2 C3 118.45(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
O1 N1 C1 C2 179.04(16) . . . . ?
C5 N1 C1 C2 -1.0(3) . . . . ?
N1 C1 C2 C3 -0.6(3) . . . . ?
N1 C1 C2 C6 177.06(16) . . . . ?
C1 C2 C3 C4 1.8(2) . . . . ?
C6 C2 C3 C4 -175.63(17) . . . . ?
C1 C2 C3 N2 -178.51(15) . . . . ?
C6 C2 C3 N2 4.1(3) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
N2 C3 C4 C5 178.90(15) . . . . ?
O1 N1 C5 C4 -178.58(16) . . . . ?
C1 N1 C5 C4 1.5(3) . . . . ?
C3 C4 C5 N1 -0.3(3) . . . . ?
C4 C3 N2 O3 14.6(2) . . . . ?
C2 C3 N2 O3 -165.13(17) . . . . ?
C4 C3 N2 O2 -164.53(17) . . . . ?
C2 C3 N2 O2 15.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.905
_diffrn_reflns_theta_full        28.72
_diffrn_measured_fraction_theta_full 0.905
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.032
_database_code_depnum_ccdc_archive 'CCDC 979905'
#######################################################################
#
#                 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_3-methyl-4-nitropyridine-N-oxide_255K

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-methyl-4-nitropyridine-N-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13

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           Orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   21.2997(10)
_cell_length_b                   6.1229(3)
_cell_length_c                   5.1413(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     670.51(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    255(2)
_cell_measurement_reflns_used    1885
_cell_measurement_theta_min      3.46
_cell_measurement_theta_max      28.70

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9635
_exptl_absorpt_correction_T_max  0.9754
_exptl_absorpt_process_details   '(CrysAlis Pro; Oxford Diffraction, 2010)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      255(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  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1885
_diffrn_reflns_av_R_equivalents  0.0116
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         3.46
_diffrn_reflns_theta_max         28.70
_reflns_number_total             946
_reflns_number_gt                842
_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          
; 
 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)+(0.0474P)²+0.0533P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.032(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_number_reflns         946
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0876
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_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
N1 N 0.15392(7) 0.0493(2) 0.5049(3) 0.0371(4) Uani 1 1 d . . .
C1 C 0.17904(8) 0.1784(3) 0.3183(4) 0.0350(4) Uani 1 1 d . . .
H1 H 0.2159 0.1334 0.2377 0.042 Uiso 1 1 calc R . .
C2 C 0.15242(8) 0.3746(3) 0.2417(3) 0.0314(4) Uani 1 1 d . . .
C3 C 0.09692(8) 0.4330(3) 0.3688(3) 0.0304(4) Uani 1 1 d . . .
C4 C 0.07179(8) 0.3035(3) 0.5644(4) 0.0353(4) Uani 1 1 d . . .
H2 H 0.0354 0.3469 0.6499 0.042 Uiso 1 1 calc R . .
C5 C 0.10064(9) 0.1120(3) 0.6310(4) 0.0391(5) Uani 1 1 d . . .
H3 H 0.0839 0.0249 0.7621 0.047 Uiso 1 1 calc R . .
O1 O 0.18064(7) -0.1342(2) 0.5648(3) 0.0549(4) Uani 1 1 d . . .
C6 C 0.18692(9) 0.5064(3) 0.0414(4) 0.0409(5) Uani 1 1 d . . .
H4 H 0.2233 0.4273 -0.0155 0.061 Uiso 1 1 calc R . .
H5 H 0.1997 0.6432 0.1160 0.061 Uiso 1 1 calc R . .
H6 H 0.1598 0.5331 -0.1044 0.061 Uiso 1 1 calc R . .
N2 N 0.06263(7) 0.6329(3) 0.3052(3) 0.0392(4) Uani 1 1 d . . .
O2 O 0.07503(8) 0.7267(3) 0.1020(3) 0.0646(5) Uani 1 1 d . . .
O3 O 0.02245(7) 0.6972(2) 0.4567(3) 0.0540(4) Uani 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
N1 0.0362(8) 0.0300(7) 0.0452(9) 0.0067(8) -0.0079(7) 0.0003(6)
C1 0.0304(8) 0.0349(9) 0.0398(9) 0.0013(8) 0.0004(8) 0.0013(7)
C2 0.0300(8) 0.0327(8) 0.0315(9) 0.0016(8) -0.0038(7) -0.0033(7)
C3 0.0288(8) 0.0301(8) 0.0324(8) 0.0013(7) -0.0055(7) -0.0006(6)
C4 0.0301(8) 0.0388(9) 0.0371(9) 0.0004(9) 0.0027(8) -0.0031(7)
C5 0.0382(9) 0.0382(9) 0.0409(10) 0.0094(9) -0.0005(8) -0.0089(8)
O1 0.0548(8) 0.0368(7) 0.0732(11) 0.0175(8) -0.0075(9) 0.0110(6)
C6 0.0384(9) 0.0455(10) 0.0388(9) 0.0089(10) 0.0057(8) -0.0017(8)
N2 0.0351(8) 0.0356(8) 0.0468(9) 0.0049(8) -0.0045(7) 0.0022(7)
O2 0.0587(10) 0.0679(10) 0.0674(10) 0.0378(9) 0.0064(9) 0.0197(8)
O3 0.0513(8) 0.0489(8) 0.0619(9) -0.0035(9) 0.0066(8) 0.0165(6)

_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
N1 O1 1.2964(18) . ?
N1 C1 1.353(2) . ?
N1 C5 1.362(2) . ?
C1 C2 1.386(2) . ?
C2 C3 1.397(2) . ?
C2 C6 1.501(2) . ?
C3 C4 1.388(2) . ?
C3 N2 1.462(2) . ?
C4 C5 1.367(3) . ?
N2 O2 1.221(2) . ?
N2 O3 1.223(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
O1 N1 C1 120.07(16) . . ?
O1 N1 C5 119.80(16) . . ?
C1 N1 C5 120.14(15) . . ?
N1 C1 C2 123.10(16) . . ?
C1 C2 C3 115.79(16) . . ?
C1 C2 C6 117.44(16) . . ?
C3 C2 C6 126.72(16) . . ?
C4 C3 C2 121.28(16) . . ?
C4 C3 N2 116.58(15) . . ?
C2 C3 N2 122.14(15) . . ?
C5 C4 C3 119.87(17) . . ?
N1 C5 C4 119.79(17) . . ?
O2 N2 O3 123.04(17) . . ?
O2 N2 C3 118.49(17) . . ?
O3 N2 C3 118.47(15) . . ?

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
O1 N1 C1 C2 178.92(16) . . . . ?
C5 N1 C1 C2 -1.3(3) . . . . ?
N1 C1 C2 C3 -0.3(3) . . . . ?
N1 C1 C2 C6 177.17(16) . . . . ?
C1 C2 C3 C4 1.8(2) . . . . ?
C6 C2 C3 C4 -175.42(17) . . . . ?
C1 C2 C3 N2 -178.65(16) . . . . ?
C6 C2 C3 N2 4.1(3) . . . . ?
C2 C3 C4 C5 -1.7(3) . . . . ?
N2 C3 C4 C5 178.78(15) . . . . ?
O1 N1 C5 C4 -178.73(16) . . . . ?
C1 N1 C5 C4 1.5(3) . . . . ?
C3 C4 C5 N1 0.0(3) . . . . ?
C4 C3 N2 O2 -164.80(17) . . . . ?
C2 C3 N2 O2 15.7(2) . . . . ?
C4 C3 N2 O3 14.5(2) . . . . ?
C2 C3 N2 O3 -165.04(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.907
_diffrn_reflns_theta_full        28.70
_diffrn_measured_fraction_theta_full 0.907
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.031
_database_code_depnum_ccdc_archive 'CCDC 979906'
#######################################################################
#
#                 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_3-methyl-4-nitropyridine-N-oxide_270K

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-methyl-4-nitropyridine-N-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13

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           Orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   21.3430(10)
_cell_length_b                   6.1262(3)
_cell_length_c                   5.1430(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     672.45(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    270(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9636
_exptl_absorpt_correction_T_max  0.9755
_exptl_absorpt_process_details   '(CrysAlis Pro; Oxford Diffraction, 2010)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      270(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            1890
_diffrn_reflns_av_R_equivalents  0.0131
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         3.46
_diffrn_reflns_theta_max         28.66
_reflns_number_total             949
_reflns_number_gt                843
_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          
; 
 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)+(0.0413P)²+0.0744P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.035(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_number_reflns         949
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0863
_refine_ls_wR_factor_gt          0.0813
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_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
N1 N 0.15399(7) 0.0490(2) 0.5060(3) 0.0394(4) Uani 1 1 d . . .
C1 C 0.17916(8) 0.1783(3) 0.3198(4) 0.0374(4) Uani 1 1 d . . .
H1 H 0.2161 0.1336 0.2400 0.045 Uiso 1 1 calc R . .
C2 C 0.15244(8) 0.3742(3) 0.2426(3) 0.0329(4) Uani 1 1 d . . .
C3 C 0.09693(8) 0.4318(3) 0.3696(4) 0.0326(4) Uani 1 1 d . . .
C4 C 0.07177(8) 0.3026(3) 0.5647(4) 0.0369(4) Uani 1 1 d . . .
H2 H 0.0354 0.3457 0.6497 0.044 Uiso 1 1 calc R . .
C5 C 0.10072(9) 0.1112(3) 0.6316(4) 0.0413(5) Uani 1 1 d . . .
H3 H 0.0841 0.0240 0.7624 0.050 Uiso 1 1 calc R . .
O1 O 0.18073(7) -0.1343(2) 0.5666(4) 0.0585(5) Uani 1 1 d . . .
C6 C 0.18689(9) 0.5055(3) 0.0430(4) 0.0443(5) Uani 1 1 d . . .
H4 H 0.2232 0.4263 -0.0137 0.067 Uiso 1 1 calc R . .
H5 H 0.1996 0.6421 0.1175 0.067 Uiso 1 1 calc R . .
H6 H 0.1599 0.5322 -0.1030 0.067 Uiso 1 1 calc R . .
N2 N 0.06261(7) 0.6320(3) 0.3059(3) 0.0416(4) Uani 1 1 d . . .
O2 O 0.07491(8) 0.7250(3) 0.1023(3) 0.0696(5) Uani 1 1 d . . .
O3 O 0.02247(7) 0.6956(2) 0.4565(3) 0.0573(5) Uani 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
N1 0.0393(8) 0.0316(7) 0.0472(9) 0.0078(8) -0.0080(7) -0.0003(6)
C1 0.0323(8) 0.0369(9) 0.0430(10) 0.0017(9) -0.0001(8) 0.0015(7)
C2 0.0320(8) 0.0337(8) 0.0330(9) 0.0022(8) -0.0037(7) -0.0041(7)
C3 0.0310(8) 0.0308(8) 0.0360(9) 0.0020(8) -0.0055(7) -0.0004(7)
C4 0.0325(9) 0.0399(9) 0.0384(9) 0.0017(9) 0.0019(8) -0.0036(7)
C5 0.0409(9) 0.0407(10) 0.0425(10) 0.0091(9) -0.0014(9) -0.0089(8)
O1 0.0587(9) 0.0390(7) 0.0777(11) 0.0184(8) -0.0083(9) 0.0115(7)
C6 0.0418(9) 0.0503(11) 0.0409(10) 0.0099(10) 0.0058(9) -0.0019(9)
N2 0.0366(8) 0.0383(8) 0.0498(9) 0.0039(8) -0.0047(8) 0.0025(7)
O2 0.0647(10) 0.0726(11) 0.0714(11) 0.0397(10) 0.0071(9) 0.0217(9)
O3 0.0533(8) 0.0528(8) 0.0658(10) -0.0043(9) 0.0074(8) 0.0179(7)

_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
N1 O1 1.2976(19) . ?
N1 C1 1.354(2) . ?
N1 C5 1.362(2) . ?
C1 C2 1.387(2) . ?
C2 C3 1.398(2) . ?
C2 C6 1.497(2) . ?
C3 C4 1.386(2) . ?
C3 N2 1.465(2) . ?
C4 C5 1.369(3) . ?
N2 O3 1.219(2) . ?
N2 O2 1.221(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
O1 N1 C1 120.09(17) . . ?
O1 N1 C5 119.71(17) . . ?
C1 N1 C5 120.20(15) . . ?
N1 C1 C2 123.05(17) . . ?
C1 C2 C3 115.68(16) . . ?
C1 C2 C6 117.33(16) . . ?
C3 C2 C6 126.93(16) . . ?
C4 C3 C2 121.46(16) . . ?
C4 C3 N2 116.49(16) . . ?
C2 C3 N2 122.04(15) . . ?
C5 C4 C3 119.75(17) . . ?
N1 C5 C4 119.82(17) . . ?
O3 N2 O2 123.16(18) . . ?
O3 N2 C3 118.49(16) . . ?
O2 N2 C3 118.34(17) . . ?

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
O1 N1 C1 C2 178.87(16) . . . . ?
C5 N1 C1 C2 -1.5(3) . . . . ?
N1 C1 C2 C3 -0.1(3) . . . . ?
N1 C1 C2 C6 177.30(16) . . . . ?
C1 C2 C3 C4 1.7(2) . . . . ?
C6 C2 C3 C4 -175.46(18) . . . . ?
C1 C2 C3 N2 -178.87(16) . . . . ?
C6 C2 C3 N2 4.0(3) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
N2 C3 C4 C5 178.90(15) . . . . ?
O1 N1 C5 C4 -178.78(17) . . . . ?
C1 N1 C5 C4 1.6(3) . . . . ?
C3 C4 C5 N1 -0.1(3) . . . . ?
C4 C3 N2 O3 14.3(2) . . . . ?
C2 C3 N2 O3 -165.14(17) . . . . ?
C4 C3 N2 O2 -164.46(17) . . . . ?
C2 C3 N2 O2 16.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.912
_diffrn_reflns_theta_full        28.66
_diffrn_measured_fraction_theta_full 0.912
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.031
_database_code_depnum_ccdc_archive 'CCDC 979907'
#######################################################################
#
#                 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_3-methyl-4-nitropyridine_N-oxide_1.29GPa

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-methyl-4-nitropyridineN-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13

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           Orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   20.5114(19)
_cell_length_b                   6.016(4)
_cell_length_c                   5.005(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     617.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       1290000
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.5963
_exptl_absorpt_correction_T_max  0.9468
_exptl_absorpt_process_details   
;   
Katrusiak, A. (2003). REDSHABS - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Poznań.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467
;
_exptl_special_details           
; 
 Data were collected at room temperature and pressure of 0.12(3) GPa
 (120000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique.
 Pressure was determined by monitoring the shift of the ruby
 R1-fluorescence line.
;
_diffrn_ambient_temperature      296(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  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       
;HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2532
_diffrn_reflns_av_R_equivalents  0.0940
_diffrn_reflns_av_sigmaI/netI    0.0522
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         4.19
_diffrn_reflns_theta_max         28.24
_reflns_number_total             314
_reflns_number_gt                263
_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          
; 
 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)+(0.0299P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_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   2(5)
_refine_ls_number_reflns         314
_refine_ls_number_parameters     100
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.0709
_refine_ls_wR_factor_gt          0.0662
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_restrained_S_all      1.094
_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
N1 N 0.15244(17) 0.057(2) 0.4965(9) 0.042(4) Uani 1 1 d DU . .
C1 C 0.17850(17) 0.182(2) 0.3007(9) 0.032(4) Uani 1 1 d DU . .
H1 H 0.2155 0.1296 0.2134 0.038 Uiso 1 1 calc R . .
C2 C 0.15267(18) 0.384(2) 0.2237(8) 0.029(4) Uani 1 1 d DU . .
C3 C 0.0972(2) 0.451(2) 0.3603(8) 0.032(4) Uani 1 1 d DU . .
C4 C 0.0709(2) 0.3257(18) 0.5638(9) 0.032(4) Uani 1 1 d DU . .
H2 H 0.0340 0.3754 0.6539 0.038 Uiso 1 1 calc R . .
C5 C 0.0988(2) 0.1306(18) 0.6321(9) 0.039(4) Uani 1 1 d DU . .
H3 H 0.0816 0.0463 0.7710 0.046 Uiso 1 1 calc R . .
O1 O 0.17876(16) -0.136(2) 0.5567(7) 0.062(4) Uani 1 1 d U . .
C6 C 0.18871(17) 0.516(3) 0.0175(7) 0.041(4) Uani 1 1 d U . .
H4 H 0.2262 0.4336 -0.0411 0.061 Uiso 1 1 calc R . .
H5 H 0.2024 0.6546 0.0934 0.061 Uiso 1 1 calc R . .
H6 H 0.1606 0.5435 -0.1321 0.061 Uiso 1 1 calc R . .
N2 N 0.06290(18) 0.650(2) 0.2959(8) 0.038(4) Uani 1 1 d U . .
O2 O 0.07555(13) 0.7477(18) 0.0859(6) 0.052(4) Uani 1 1 d U . .
O3 O 0.02068(13) 0.717(2) 0.4508(5) 0.053(4) Uani 1 1 d U . .

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
N1 0.034(2) 0.047(13) 0.046(2) 0.000(5) -0.011(2) -0.005(5)
C1 0.029(2) 0.023(13) 0.043(3) 0.008(6) 0.002(2) -0.015(6)
C2 0.027(2) 0.033(13) 0.028(2) 0.000(5) -0.0038(18) 0.001(5)
C3 0.031(2) 0.030(13) 0.034(3) 0.005(5) -0.011(2) 0.011(6)
C4 0.034(2) 0.024(13) 0.037(3) 0.019(5) 0.003(2) -0.010(6)
C5 0.038(3) 0.039(13) 0.039(3) 0.009(5) -0.002(2) -0.005(6)
O1 0.055(2) 0.057(13) 0.074(3) 0.013(6) -0.0059(17) 0.016(5)
C6 0.0381(19) 0.039(13) 0.045(2) -0.009(6) 0.0002(18) -0.006(5)
N2 0.0292(17) 0.039(13) 0.046(2) -0.003(5) -0.003(2) 0.000(5)
O2 0.0545(18) 0.042(12) 0.0603(18) 0.022(5) 0.0078(14) 0.011(4)
O3 0.0489(16) 0.054(12) 0.0562(17) -0.001(4) 0.0063(14) 0.024(4)

_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
N1 O1 1.319(17) . ?
N1 C1 1.344(12) . ?
N1 C5 1.365(6) . ?
C1 C2 1.380(7) . ?
C2 C3 1.388(8) . ?
C2 C6 1.497(12) . ?
C3 C4 1.376(6) . ?
C3 N2 1.428(17) . ?
C4 C5 1.350(7) . ?
N2 O3 1.230(6) . ?
N2 O2 1.231(8) . ?

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
O1 N1 C1 119.7(6) . . ?
O1 N1 C5 120.0(8) . . ?
C1 N1 C5 120.3(10) . . ?
N1 C1 C2 122.7(7) . . ?
C1 C2 C3 115.6(7) . . ?
C1 C2 C6 118.0(7) . . ?
C3 C2 C6 126.2(10) . . ?
C4 C3 C2 121.8(9) . . ?
C4 C3 N2 115.7(5) . . ?
C2 C3 N2 122.4(8) . . ?
C5 C4 C3 119.7(6) . . ?
C4 C5 N1 119.8(8) . . ?
O3 N2 O2 122.0(10) . . ?
O3 N2 C3 118.7(6) . . ?
O2 N2 C3 119.3(6) . . ?

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
O1 N1 C1 C2 178.6(6) . . . . ?
C5 N1 C1 C2 -1.1(9) . . . . ?
N1 C1 C2 C3 -0.6(7) . . . . ?
N1 C1 C2 C6 175.5(6) . . . . ?
C1 C2 C3 C4 1.7(8) . . . . ?
C6 C2 C3 C4 -174.1(6) . . . . ?
C1 C2 C3 N2 -177.0(7) . . . . ?
C6 C2 C3 N2 7.3(10) . . . . ?
C2 C3 C4 C5 -1.0(9) . . . . ?
N2 C3 C4 C5 177.8(6) . . . . ?
C3 C4 C5 N1 -0.8(8) . . . . ?
O1 N1 C5 C4 -177.9(7) . . . . ?
C1 N1 C5 C4 1.9(9) . . . . ?
C4 C3 N2 O3 12.7(10) . . . . ?
C2 C3 N2 O3 -168.5(7) . . . . ?
C4 C3 N2 O2 -166.0(6) . . . . ?
C2 C3 N2 O2 12.8(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.228
_diffrn_reflns_theta_full        28.24
_diffrn_measured_fraction_theta_full 0.228
_refine_diff_density_max         0.054
_refine_diff_density_min         -0.062
_refine_diff_density_rms         0.017
_database_code_depnum_ccdc_archive 'CCDC 979908'
#######################################################################
#
#                 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_3-methyl-4-nitropyridine_N-oxide_1.58GPa

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-methyl-4-nitropyridineN-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13

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           Orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   20.343(2)
_cell_length_b                   6.001(4)
_cell_length_c                   4.9855(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     608.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       1580000
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.5872
_exptl_absorpt_correction_T_max  0.9409
_exptl_absorpt_process_details   
;  
Katrusiak, A. (2003). REDSHABS - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Poznań.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467
;
_exptl_special_details           
; 
 Data were collected at room temperature and pressure of 1.58(3) GPa
 (1580000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique.
 Pressure was determined by monitoring the shift of the ruby
 R1-fluorescence line.
;
_diffrn_ambient_temperature      296(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  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       
;HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2243
_diffrn_reflns_av_R_equivalents  0.0810
_diffrn_reflns_av_sigmaI/netI    0.0464
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         4.21
_diffrn_reflns_theta_max         27.18
_reflns_number_total             302
_reflns_number_gt                268
_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          
; 
 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)+(0.0330P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_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   3(4)
_refine_ls_number_reflns         302
_refine_ls_number_parameters     100
_refine_ls_number_restraints     70
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0598
_refine_ls_wR_factor_gt          0.0560
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      0.995
_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
N1 N 0.15217(14) 0.057(2) 0.4954(8) 0.039(4) Uani 1 1 d DU . .
C1 C 0.17791(16) 0.182(3) 0.2958(8) 0.030(4) Uani 1 1 d DU . .
H1 H 0.2146 0.1273 0.2055 0.036 Uiso 1 1 calc R . .
C2 C 0.15269(15) 0.384(2) 0.2193(7) 0.029(4) Uani 1 1 d DU . .
C3 C 0.09664(16) 0.448(3) 0.3612(7) 0.028(4) Uani 1 1 d DU . .
C4 C 0.07018(18) 0.329(2) 0.5637(7) 0.026(4) Uani 1 1 d DU . .
H2 H 0.0328 0.3787 0.6523 0.031 Uiso 1 1 calc R . .
C5 C 0.09833(17) 0.140(3) 0.6332(8) 0.030(4) Uani 1 1 d DU . .
H3 H 0.0817 0.0601 0.7781 0.036 Uiso 1 1 calc R . .
O1 O 0.17848(14) -0.1352(19) 0.5534(6) 0.056(4) Uani 1 1 d U . .
C6 C 0.18871(14) 0.521(3) 0.0114(6) 0.034(4) Uani 1 1 d U . .
H4 H 0.2267 0.4407 -0.0497 0.051 Uiso 1 1 calc R . .
H5 H 0.2023 0.6598 0.0895 0.051 Uiso 1 1 calc R . .
H6 H 0.1600 0.5497 -0.1376 0.051 Uiso 1 1 calc R . .
N2 N 0.06271(15) 0.658(2) 0.2968(7) 0.033(4) Uani 1 1 d DU . .
O2 O 0.07558(10) 0.7552(16) 0.0846(5) 0.050(4) Uani 1 1 d U . .
O3 O 0.02045(11) 0.7249(16) 0.4508(4) 0.049(4) Uani 1 1 d U . .

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
N1 0.028(2) 0.038(13) 0.051(2) 0.009(5) -0.0158(19) -0.006(5)
C1 0.029(2) 0.023(13) 0.039(2) 0.009(5) 0.0016(18) -0.014(5)
C2 0.0288(18) 0.030(13) 0.028(2) -0.006(5) -0.0051(15) 0.010(5)
C3 0.0252(16) 0.024(13) 0.036(2) 0.012(5) -0.0093(17) 0.008(5)
C4 0.0285(19) 0.018(13) 0.031(2) 0.011(4) -0.0016(16) -0.009(5)
C5 0.0252(19) 0.030(13) 0.036(2) 0.003(5) -0.0047(16) -0.005(5)
O1 0.0484(19) 0.052(12) 0.069(2) 0.005(5) -0.0066(14) 0.022(4)
C6 0.0356(15) 0.030(13) 0.0362(16) 0.007(5) 0.0006(15) -0.014(4)
N2 0.0267(14) 0.031(12) 0.0421(18) -0.003(4) -0.0030(15) -0.007(4)
O2 0.0484(14) 0.045(12) 0.0565(16) 0.021(4) 0.0050(11) 0.012(3)
O3 0.0443(12) 0.052(12) 0.0509(13) 0.003(4) 0.0042(11) 0.019(4)

_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
N1 O1 1.306(16) . ?
N1 C1 1.349(11) . ?
N1 C5 1.384(10) . ?
C1 C2 1.373(17) . ?
C2 C3 1.397(7) . ?
C2 C6 1.513(11) . ?
C3 C4 1.350(11) . ?
C3 N2 1.469(17) . ?
C4 C5 1.32(2) . ?
N2 O3 1.221(5) . ?
N2 O2 1.237(7) . ?

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
O1 N1 C1 119.5(6) . . ?
O1 N1 C5 122.0(9) . . ?
C1 N1 C5 118.4(11) . . ?
N1 C1 C2 123.3(6) . . ?
C1 C2 C3 114.1(8) . . ?
C1 C2 C6 119.4(6) . . ?
C3 C2 C6 126.3(10) . . ?
C4 C3 C2 123.9(11) . . ?
C4 C3 N2 115.5(7) . . ?
C2 C3 N2 120.6(8) . . ?
C5 C4 C3 118.8(7) . . ?
C4 C5 N1 121.4(8) . . ?
O3 N2 O2 122.0(8) . . ?
O3 N2 C3 118.4(6) . . ?
O2 N2 C3 119.5(5) . . ?

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
O1 N1 C1 C2 179.0(8) . . . . ?
C5 N1 C1 C2 -1.2(10) . . . . ?
N1 C1 C2 C3 -1.7(11) . . . . ?
N1 C1 C2 C6 174.2(5) . . . . ?
C1 C2 C3 C4 2.4(11) . . . . ?
C6 C2 C3 C4 -173.1(7) . . . . ?
C1 C2 C3 N2 -178.1(7) . . . . ?
C6 C2 C3 N2 6.3(10) . . . . ?
C2 C3 C4 C5 -0.1(13) . . . . ?
N2 C3 C4 C5 -179.6(8) . . . . ?
C3 C4 C5 N1 -3.1(14) . . . . ?
O1 N1 C5 C4 -176.4(9) . . . . ?
C1 N1 C5 C4 3.7(12) . . . . ?
C4 C3 N2 O3 10.7(10) . . . . ?
C2 C3 N2 O3 -168.8(6) . . . . ?
C4 C3 N2 O2 -166.2(6) . . . . ?
C2 C3 N2 O2 14.2(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.247
_diffrn_reflns_theta_full        27.18
_diffrn_measured_fraction_theta_full 0.247
_refine_diff_density_max         0.066
_refine_diff_density_min         -0.067
_refine_diff_density_rms         0.019
_database_code_depnum_ccdc_archive 'CCDC 979909'
#######################################################################
#
#                 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_3-methyl-4-nitropyridine_N-oxide_2.04GPa

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-methyl-4-nitropyridineN-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13

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           Orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   20.141(2)
_cell_length_b                   5.973(5)
_cell_length_c                   4.9650(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     597.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       2040000
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.6036
_exptl_absorpt_correction_T_max  0.9458
_exptl_absorpt_process_details   
;  
Katrusiak, A. (2003). REDSHABS - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Poznań.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467
;
_exptl_special_details           
; 
 Data were collected at room temperature and pressure of 2.04(3) GPa
 (2040000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique.
 Pressure was determined by monitoring the shift of the ruby
 R1-fluorescence line.
;
_diffrn_ambient_temperature      296(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  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       
;HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2268
_diffrn_reflns_av_R_equivalents  0.0799
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         4.23
_diffrn_reflns_theta_max         27.37
_reflns_number_total             304
_reflns_number_gt                260
_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          
; 
 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)+(0.0491P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_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   2(4)
_refine_ls_number_reflns         304
_refine_ls_number_parameters     100
_refine_ls_number_restraints     76
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0757
_refine_ls_wR_factor_gt          0.0700
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.001
_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
N1 N 0.15204(15) 0.066(2) 0.4888(8) 0.042(4) Uani 1 1 d DU . .
C1 C 0.17819(17) 0.1854(19) 0.2903(9) 0.034(4) Uani 1 1 d DU . .
H1 H 0.2149 0.1297 0.1983 0.040 Uiso 1 1 calc R . .
C2 C 0.15222(15) 0.3900(16) 0.2171(8) 0.029(4) Uani 1 1 d DU . .
C3 C 0.09682(17) 0.458(2) 0.3589(7) 0.030(4) Uani 1 1 d DU . .
C4 C 0.06982(17) 0.3358(13) 0.5665(7) 0.029(4) Uani 1 1 d DU . .
H2 H 0.0328 0.3880 0.6589 0.035 Uiso 1 1 calc R . .
C5 C 0.09819(17) 0.1376(16) 0.6340(8) 0.033(4) Uani 1 1 d DU . .
H3 H 0.0815 0.0522 0.7753 0.040 Uiso 1 1 calc R . .
O1 O 0.17768(14) -0.133(2) 0.5519(6) 0.057(4) Uani 1 1 d U . .
C6 C 0.18927(14) 0.520(3) 0.0093(6) 0.038(4) Uani 1 1 d U . .
H4 H 0.2272 0.4354 -0.0489 0.057 Uiso 1 1 calc R . .
H5 H 0.2037 0.6595 0.0849 0.057 Uiso 1 1 calc R . .
H6 H 0.1608 0.5482 -0.1418 0.057 Uiso 1 1 calc R . .
N2 N 0.06287(14) 0.6618(19) 0.2957(7) 0.032(4) Uani 1 1 d DU . .
O2 O 0.07577(11) 0.7595(16) 0.0830(6) 0.049(4) Uani 1 1 d DU . .
O3 O 0.02047(10) 0.7304(12) 0.4502(4) 0.052(4) Uani 1 1 d DU . .

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
N1 0.0345(19) 0.043(13) 0.049(2) 0.015(5) -0.0191(18) 0.001(5)
C1 0.0285(18) 0.031(13) 0.041(2) 0.002(6) 0.0090(19) -0.020(5)
C2 0.0295(18) 0.027(13) 0.029(2) -0.007(5) -0.0049(15) 0.015(5)
C3 0.0260(15) 0.026(13) 0.040(2) 0.006(5) -0.0091(17) 0.014(5)
C4 0.0304(17) 0.025(13) 0.032(2) 0.009(4) -0.0006(16) -0.008(5)
C5 0.0296(18) 0.036(13) 0.034(2) 0.001(4) 0.0008(16) -0.009(5)
O1 0.0501(18) 0.058(13) 0.063(2) 0.016(5) -0.0050(15) 0.012(4)
C6 0.0346(14) 0.040(13) 0.039(2) 0.011(5) -0.0007(15) -0.010(4)
N2 0.0286(14) 0.029(12) 0.0384(17) -0.003(4) 0.0014(16) -0.008(4)
O2 0.0524(14) 0.037(12) 0.0562(16) 0.029(4) 0.0053(12) 0.017(4)
O3 0.0447(12) 0.063(12) 0.0474(13) 0.007(4) 0.0042(11) 0.019(4)

_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
N1 C1 1.325(10) . ?
N1 O1 1.337(16) . ?
N1 C5 1.370(6) . ?
C1 C2 1.378(7) . ?
C2 C3 1.381(7) . ?
C2 C6 1.491(10) . ?
C3 C4 1.375(6) . ?
C3 N2 1.430(14) . ?
C4 C5 1.357(7) . ?
N2 O3 1.219(4) . ?
N2 O2 1.234(7) . ?

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
C1 N1 O1 120.0(6) . . ?
C1 N1 C5 122.6(9) . . ?
O1 N1 C5 117.4(7) . . ?
N1 C1 C2 121.4(6) . . ?
C1 C2 C3 115.7(6) . . ?
C1 C2 C6 117.0(6) . . ?
C3 C2 C6 127.2(9) . . ?
C4 C3 C2 123.0(9) . . ?
C4 C3 N2 115.3(5) . . ?
C2 C3 N2 121.7(6) . . ?
C5 C4 C3 118.8(5) . . ?
C4 C5 N1 118.3(7) . . ?
O3 N2 O2 121.8(8) . . ?
O3 N2 C3 118.9(6) . . ?
O2 N2 C3 119.3(5) . . ?

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
O1 N1 C1 C2 178.8(6) . . . . ?
C5 N1 C1 C2 -0.2(9) . . . . ?
N1 C1 C2 C3 -1.6(7) . . . . ?
N1 C1 C2 C6 174.3(6) . . . . ?
C1 C2 C3 C4 2.1(8) . . . . ?
C6 C2 C3 C4 -173.3(6) . . . . ?
C1 C2 C3 N2 -177.0(5) . . . . ?
C6 C2 C3 N2 7.7(9) . . . . ?
C2 C3 C4 C5 -0.8(8) . . . . ?
N2 C3 C4 C5 178.3(5) . . . . ?
C3 C4 C5 N1 -1.0(7) . . . . ?
C1 N1 C5 C4 1.6(8) . . . . ?
O1 N1 C5 C4 -177.5(6) . . . . ?
C4 C3 N2 O3 11.4(8) . . . . ?
C2 C3 N2 O3 -169.5(5) . . . . ?
C4 C3 N2 O2 -166.4(5) . . . . ?
C2 C3 N2 O2 12.7(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.248
_diffrn_reflns_theta_full        27.37
_diffrn_measured_fraction_theta_full 0.248
_refine_diff_density_max         0.069
_refine_diff_density_min         -0.080
_refine_diff_density_rms         0.021
_database_code_depnum_ccdc_archive 'CCDC 979910'
#######################################################################
#
#                 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_3-methyl-4-nitropyridine_N-oxide_2.68GPa

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-methyl-4-nitropyridineN-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13

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           Orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   19.878(3)
_cell_length_b                   5.938(4)
_cell_length_c                   4.9394(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     583.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       2680000
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.6109
_exptl_absorpt_correction_T_max  0.9448
_exptl_absorpt_process_details   
;  
Katrusiak, A. (2003). REDSHABS - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Poznań.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467
;
_exptl_special_details           
; 
 Data were collected at room temperature and pressure of 2.68(3) GPa
 (2680000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique.
 Pressure was determined by monitoring the shift of the ruby
 R1-fluorescence line.
;
_diffrn_ambient_temperature      296(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  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       
;HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2235
_diffrn_reflns_av_R_equivalents  0.0715
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         4.25
_diffrn_reflns_theta_max         27.61
_reflns_number_total             302
_reflns_number_gt                273
_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          
; 
 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)+(0.0519P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_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   -7(4)
_refine_ls_number_reflns         302
_refine_ls_number_parameters     100
_refine_ls_number_restraints     73
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0793
_refine_ls_wR_factor_gt          0.0758
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.035
_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
N1 N 0.15192(15) 0.059(2) 0.4886(8) 0.034(4) Uani 1 1 d DU . .
C1 C 0.17733(18) 0.189(3) 0.2848(8) 0.029(4) Uani 1 1 d DU . .
H1 H 0.2145 0.1350 0.1908 0.035 Uiso 1 1 calc R . .
C2 C 0.15189(16) 0.3926(17) 0.2103(8) 0.025(4) Uani 1 1 d DU . .
C3 C 0.09613(18) 0.465(2) 0.3557(8) 0.024(4) Uani 1 1 d DU . .
C4 C 0.07010(18) 0.3385(18) 0.5670(7) 0.024(4) Uani 1 1 d DU . .
H2 H 0.0330 0.3912 0.6624 0.028 Uiso 1 1 calc R . .
C5 C 0.09835(17) 0.1379(18) 0.6360(8) 0.029(4) Uani 1 1 d DU . .
H3 H 0.0816 0.0556 0.7813 0.035 Uiso 1 1 calc R . .
O1 O 0.17788(15) -0.138(2) 0.5468(7) 0.052(4) Uani 1 1 d U . .
C6 C 0.19000(16) 0.520(3) 0.0031(6) 0.033(4) Uani 1 1 d U . .
H4 H 0.2282 0.4334 -0.0543 0.049 Uiso 1 1 calc R . .
H5 H 0.2051 0.6603 0.0789 0.049 Uiso 1 1 calc R . .
H6 H 0.1614 0.5496 -0.1496 0.049 Uiso 1 1 calc R . .
N2 N 0.06200(16) 0.671(2) 0.2910(7) 0.026(4) Uani 1 1 d U . .
O2 O 0.07577(13) 0.7655(15) 0.0789(6) 0.044(4) Uani 1 1 d DU . .
O3 O 0.01998(11) 0.7382(18) 0.4490(5) 0.044(4) Uani 1 1 d U . .

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
N1 0.0302(19) 0.033(13) 0.0383(19) 0.003(4) -0.0135(18) 0.006(5)
C1 0.027(2) 0.026(13) 0.035(2) -0.002(5) 0.0044(19) -0.014(5)
C2 0.026(2) 0.021(13) 0.029(2) -0.005(5) -0.0074(16) 0.000(5)
C3 0.0225(16) 0.018(13) 0.030(2) 0.000(4) -0.0053(16) 0.004(5)
C4 0.0266(18) 0.018(13) 0.026(2) 0.004(4) 0.0022(16) -0.010(5)
C5 0.0255(18) 0.030(13) 0.032(2) 0.003(4) -0.0056(16) -0.002(5)
O1 0.0413(18) 0.051(12) 0.063(2) 0.005(5) -0.0060(16) 0.013(4)
C6 0.0335(15) 0.033(13) 0.032(2) 0.013(5) -0.0025(16) -0.006(4)
N2 0.0244(15) 0.023(12) 0.0322(18) -0.004(4) -0.0002(16) -0.009(4)
O2 0.0463(14) 0.036(12) 0.0482(15) 0.025(4) 0.0045(12) 0.009(4)
O3 0.0374(12) 0.050(12) 0.0453(13) 0.001(4) 0.0025(12) 0.019(4)

_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
N1 O1 1.307(16) . ?
N1 C1 1.367(12) . ?
N1 C5 1.373(6) . ?
C1 C2 1.361(17) . ?
C2 C3 1.389(7) . ?
C2 C6 1.482(10) . ?
C3 C4 1.386(6) . ?
C3 N2 1.433(17) . ?
C4 C5 1.360(7) . ?
N2 O3 1.212(5) . ?
N2 O2 1.221(8) . ?

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
O1 N1 C1 121.4(6) . . ?
O1 N1 C5 119.7(7) . . ?
C1 N1 C5 118.9(9) . . ?
C2 C1 N1 124.4(6) . . ?
C1 C2 C3 115.5(7) . . ?
C1 C2 C6 116.8(6) . . ?
C3 C2 C6 127.4(9) . . ?
C4 C3 C2 121.3(8) . . ?
C4 C3 N2 116.9(5) . . ?
C2 C3 N2 121.7(7) . . ?
C5 C4 C3 120.6(6) . . ?
C4 C5 N1 119.2(7) . . ?
O3 N2 O2 123.7(10) . . ?
O3 N2 C3 117.7(6) . . ?
O2 N2 C3 118.6(6) . . ?

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
O1 N1 C1 C2 178.6(8) . . . . ?
C5 N1 C1 C2 -2.0(10) . . . . ?
N1 C1 C2 C3 -0.4(10) . . . . ?
N1 C1 C2 C6 174.2(6) . . . . ?
C1 C2 C3 C4 1.7(9) . . . . ?
C6 C2 C3 C4 -172.2(6) . . . . ?
C1 C2 C3 N2 -176.9(8) . . . . ?
C6 C2 C3 N2 9.2(9) . . . . ?
C2 C3 C4 C5 -0.6(8) . . . . ?
N2 C3 C4 C5 178.1(6) . . . . ?
C3 C4 C5 N1 -1.9(7) . . . . ?
O1 N1 C5 C4 -177.5(6) . . . . ?
C1 N1 C5 C4 3.2(8) . . . . ?
C4 C3 N2 O3 11.5(9) . . . . ?
C2 C3 N2 O3 -169.9(6) . . . . ?
C4 C3 N2 O2 -167.2(5) . . . . ?
C2 C3 N2 O2 11.5(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.250
_diffrn_reflns_theta_full        27.61
_diffrn_measured_fraction_theta_full 0.250
_refine_diff_density_max         0.088
_refine_diff_density_min         -0.100
_refine_diff_density_rms         0.024
_database_code_depnum_ccdc_archive 'CCDC 979911'
#######################################################################
#
#                 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_3-methyl-4-nitropyridine_N-oxide_3.57GPa

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3-methyl-4-nitropyridineN-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13

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           Orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   19.5490(16)
_cell_length_b                   5.901(4)
_cell_length_c                   4.9131(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     566.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       3570000
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.806
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.6327
_exptl_absorpt_correction_T_max  0.9487
_exptl_absorpt_process_details   
;  
Katrusiak, A. (2003). REDSHABS - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Poznań.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467
;
_exptl_special_details           
; 
 Data were collected at room temperature and pressure of 3.57(3) GPa
 (3570000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique.
 Pressure was determined by monitoring the shift of the ruby
 R1-fluorescence line.
;
_diffrn_ambient_temperature      296(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  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       
;HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2150
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         4.28
_diffrn_reflns_theta_max         27.19
_reflns_number_total             293
_reflns_number_gt                260
_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          
; 
 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)+(0.0459P)²+0.0416P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_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   3(5)
_refine_ls_number_reflns         293
_refine_ls_number_parameters     100
_refine_ls_number_restraints     89
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.0809
_refine_ls_wR_factor_gt          0.0776
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_restrained_S_all      1.117
_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
N1 N 0.15123(17) 0.058(2) 0.4831(9) 0.029(4) Uani 1 1 d DU . .
C1 C 0.17766(19) 0.1820(18) 0.2760(10) 0.027(4) Uani 1 1 d DU . .
H1 H 0.2144 0.1237 0.1783 0.032 Uiso 1 1 calc R . .
C2 C 0.15201(17) 0.3915(16) 0.2051(9) 0.021(4) Uani 1 1 d DU . .
C3 C 0.0962(2) 0.470(2) 0.3535(8) 0.022(4) Uani 1 1 d DU . .
C4 C 0.0700(2) 0.3453(13) 0.5680(8) 0.024(2) Uani 1 1 d DU . .
H2 H 0.0330 0.4005 0.6666 0.029 Uiso 1 1 calc R . .
C5 C 0.0985(2) 0.1404(16) 0.6356(9) 0.033(4) Uani 1 1 d DU . .
H3 H 0.0820 0.0587 0.7836 0.039 Uiso 1 1 calc R . .
O1 O 0.17767(17) -0.133(2) 0.5424(8) 0.048(4) Uani 1 1 d U . .
C6 C 0.19065(18) 0.522(3) -0.0050(7) 0.032(4) Uani 1 1 d U . .
H4 H 0.2294 0.4348 -0.0641 0.048 Uiso 1 1 calc R . .
H5 H 0.2060 0.6625 0.0714 0.048 Uiso 1 1 calc R . .
H6 H 0.1614 0.5517 -0.1577 0.048 Uiso 1 1 calc R . .
N2 N 0.06218(17) 0.673(2) 0.2871(8) 0.024(4) Uani 1 1 d DU . .
O2 O 0.07602(14) 0.7703(15) 0.0734(6) 0.044(2) Uani 1 1 d DU . .
O3 O 0.01950(13) 0.7463(14) 0.4477(5) 0.037(4) Uani 1 1 d DU . .

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
N1 0.028(2) 0.024(13) 0.035(2) 0.008(5) -0.012(2) 0.007(5)
C1 0.017(2) 0.022(13) 0.040(3) 0.001(6) 0.004(2) -0.008(5)
C2 0.020(2) 0.016(13) 0.027(2) -0.007(5) -0.0057(17) 0.006(5)
C3 0.023(2) 0.014(13) 0.029(3) 0.002(5) -0.0093(18) 0.000(6)
C4 0.0240(19) 0.023(6) 0.026(2) 0.011(4) 0.0001(17) -0.004(4)
C5 0.035(2) 0.031(13) 0.031(3) -0.002(5) -0.0058(18) -0.002(6)
O1 0.038(2) 0.047(13) 0.059(2) 0.004(5) -0.0099(17) 0.009(4)
C6 0.0367(18) 0.028(13) 0.031(2) 0.007(6) -0.0023(18) 0.000(5)
N2 0.0226(17) 0.018(13) 0.031(2) -0.009(4) -0.0006(18) -0.010(4)
O2 0.0494(15) 0.041(6) 0.0416(16) 0.018(3) 0.0062(14) 0.005(3)
O3 0.0399(15) 0.031(12) 0.0399(15) 0.002(4) 0.0038(13) 0.009(4)

_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
N1 O1 1.274(17) . ?
N1 C1 1.356(10) . ?
N1 C5 1.365(6) . ?
C1 C2 1.379(7) . ?
C2 C3 1.391(8) . ?
C2 C6 1.493(11) . ?
C3 C4 1.384(6) . ?
C3 N2 1.410(15) . ?
C4 C5 1.372(7) . ?
N2 O2 1.226(7) . ?
N2 O3 1.227(4) . ?

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
O1 N1 C1 119.7(6) . . ?
O1 N1 C5 119.8(7) . . ?
C1 N1 C5 120.5(9) . . ?
N1 C1 C2 122.4(6) . . ?
C1 C2 C3 116.8(7) . . ?
C1 C2 C6 116.9(6) . . ?
C3 C2 C6 126.0(8) . . ?
C4 C3 C2 120.8(9) . . ?
C4 C3 N2 117.0(5) . . ?
C2 C3 N2 122.1(6) . . ?
C5 C4 C3 120.2(6) . . ?
N1 C5 C4 119.2(7) . . ?
O2 N2 O3 122.5(9) . . ?
O2 N2 C3 119.4(5) . . ?
O3 N2 C3 118.1(6) . . ?

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
O1 N1 C1 C2 -178.9(6) . . . . ?
C5 N1 C1 C2 -1.7(9) . . . . ?
N1 C1 C2 C3 -1.2(8) . . . . ?
N1 C1 C2 C6 173.2(6) . . . . ?
C1 C2 C3 C4 2.4(8) . . . . ?
C6 C2 C3 C4 -171.5(6) . . . . ?
C1 C2 C3 N2 -175.0(6) . . . . ?
C6 C2 C3 N2 11.2(9) . . . . ?
C2 C3 C4 C5 -0.7(8) . . . . ?
N2 C3 C4 C5 176.8(5) . . . . ?
O1 N1 C5 C4 -179.4(7) . . . . ?
C1 N1 C5 C4 3.4(8) . . . . ?
C3 C4 C5 N1 -2.3(8) . . . . ?
C4 C3 N2 O2 -168.0(5) . . . . ?
C2 C3 N2 O2 9.4(10) . . . . ?
C4 C3 N2 O3 12.0(9) . . . . ?
C2 C3 N2 O3 -170.5(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.254
_diffrn_reflns_theta_full        27.19
_diffrn_measured_fraction_theta_full 0.254
_refine_diff_density_max         0.106
_refine_diff_density_min         -0.088
_refine_diff_density_rms         0.026
_database_code_depnum_ccdc_archive 'CCDC 979912'
