# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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_bo2464

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2,4-di-nitro-NNO-azoxytoluene
_chemical_name_common            ?
_chemical_melting_point          331.5
_chemical_formula_moiety         C7H6N6O6
_chemical_formula_sum            'C7 H6 N6 O6'
_chemical_formula_weight         270.18

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   5.3336(13)
_cell_length_b                   7.9688(19)
_cell_length_c                   25.494(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.454(3)
_cell_angle_gamma                90.00
_cell_volume                     1080.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    3611
_cell_measurement_theta_min      2.404
_cell_measurement_theta_max      29.131

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.9170
_exptl_absorpt_correction_T_max  0.9783
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9291
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         29.13
_reflns_number_total             2885
_reflns_number_gt                2449
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_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)+(0.0615P)²+0.0890P] 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_number_reflns         2885
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1061
_refine_ls_wR_factor_gt          0.0996
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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
O1 O 0.90719(15) 0.61073(11) 0.07112(4) 0.0274(2) Uani 1 1 d . . .
O2 O 1.43465(18) 0.76215(12) 0.08712(4) 0.0366(2) Uani 1 1 d . . .
O3 O 1.3369(2) 0.66481(13) 0.00842(4) 0.0381(3) Uani 1 1 d . . .
O4 O 0.53791(18) 0.41766(11) 0.23065(4) 0.0336(2) Uani 1 1 d . . .
O5 O 0.06425(18) 0.26715(12) 0.26346(4) 0.0337(2) Uani 1 1 d . . .
O6 O 0.3853(2) 0.18570(14) 0.31460(4) 0.0418(3) Uani 1 1 d . . .
N1 N 1.05511(18) 0.49392(12) 0.08297(4) 0.0213(2) Uani 1 1 d . . .
N2 N 1.29328(18) 0.49489(13) 0.07901(4) 0.0259(2) Uani 1 1 d . . .
N3 N 1.35681(19) 0.65728(13) 0.05587(4) 0.0265(2) Uani 1 1 d . . .
N4 N 0.53177(19) 0.27411(12) 0.21163(4) 0.0230(2) Uani 1 1 d . . .
N5 N 0.3992(2) 0.15170(13) 0.22674(4) 0.0300(3) Uani 1 1 d . . .
N6 N 0.2722(2) 0.21033(13) 0.27243(4) 0.0271(2) Uani 1 1 d . . .
C1 C 0.9557(2) 0.34232(14) 0.10670(5) 0.0216(2) Uani 1 1 d . . .
C2 C 1.0206(2) 0.18076(15) 0.09049(5) 0.0237(2) Uani 1 1 d . . .
C3 C 0.9048(2) 0.04830(15) 0.11548(5) 0.0272(3) Uani 1 1 d . . .
H3 H 0.9393 -0.0634 0.1051 0.033 Uiso 1 1 calc R . .
C4 C 0.7425(2) 0.07299(15) 0.15456(5) 0.0264(3) Uani 1 1 d . . .
H4 H 0.6694 -0.0195 0.1712 0.032 Uiso 1 1 calc R . .
C5 C 0.6893(2) 0.23685(15) 0.16873(5) 0.0226(2) Uani 1 1 d . . .
C6 C 0.7924(2) 0.37387(15) 0.14488(5) 0.0219(2) Uani 1 1 d . . .
H6 H 0.7522 0.4853 0.1544 0.026 Uiso 1 1 calc R . .
C7 C 1.1953(3) 0.14620(16) 0.04815(5) 0.0290(3) Uani 1 1 d . . .
H7A H 1.1518 0.2193 0.0179 0.035 Uiso 1 1 calc R . .
H7B H 1.1790 0.0286 0.0372 0.035 Uiso 1 1 calc R . .
H7C H 1.3691 0.1682 0.0618 0.035 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0222(4) 0.0225(4) 0.0374(5) 0.0081(4) 0.0021(4) 0.0057(3)
O2 0.0319(5) 0.0302(5) 0.0485(6) -0.0074(4) 0.0079(4) -0.0048(4)
O3 0.0404(6) 0.0419(6) 0.0327(5) 0.0080(4) 0.0069(4) -0.0013(4)
O4 0.0381(5) 0.0204(4) 0.0438(6) -0.0076(4) 0.0136(4) -0.0030(4)
O5 0.0284(5) 0.0300(5) 0.0424(6) 0.0003(4) 0.0007(4) 0.0028(4)
O6 0.0428(6) 0.0559(7) 0.0271(5) 0.0102(5) 0.0053(4) 0.0144(5)
N1 0.0214(5) 0.0204(5) 0.0219(5) 0.0015(4) -0.0005(4) 0.0024(3)
N2 0.0211(5) 0.0229(5) 0.0337(6) 0.0041(4) 0.0019(4) 0.0021(4)
N3 0.0199(5) 0.0240(5) 0.0362(6) 0.0026(4) 0.0057(4) 0.0032(4)
N4 0.0248(5) 0.0195(5) 0.0245(5) 0.0007(4) -0.0001(4) 0.0005(4)
N5 0.0388(6) 0.0235(5) 0.0291(5) -0.0003(4) 0.0111(5) -0.0034(4)
N6 0.0310(6) 0.0229(5) 0.0279(5) 0.0032(4) 0.0057(4) 0.0012(4)
C1 0.0223(5) 0.0188(5) 0.0230(5) 0.0026(4) -0.0026(4) -0.0002(4)
C2 0.0257(6) 0.0221(5) 0.0229(6) 0.0005(4) -0.0016(4) 0.0043(4)
C3 0.0353(7) 0.0192(5) 0.0271(6) -0.0009(5) 0.0013(5) 0.0029(5)
C4 0.0338(6) 0.0187(5) 0.0264(6) 0.0014(4) 0.0002(5) -0.0009(4)
C5 0.0244(6) 0.0214(5) 0.0218(5) 0.0000(4) -0.0001(4) 0.0010(4)
C6 0.0229(5) 0.0181(5) 0.0243(5) -0.0002(4) -0.0015(4) 0.0015(4)
C7 0.0335(7) 0.0251(6) 0.0289(6) -0.0007(5) 0.0050(5) 0.0052(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
O1 N1 1.2422(12) . ?
O2 N3 1.2058(14) . ?
O3 N3 1.2075(15) . ?
O4 N4 1.2419(13) . ?
O5 N6 1.2032(14) . ?
O6 N6 1.2075(15) . ?
N1 N2 1.2821(13) . ?
N1 C1 1.4685(14) . ?
N2 N3 1.4727(14) . ?
N4 N5 1.2814(15) . ?
N4 C5 1.4605(16) . ?
N5 N6 1.4687(15) . ?
C1 C6 1.3787(18) . ?
C1 C2 1.4036(16) . ?
C2 C3 1.4009(17) . ?
C2 C7 1.5053(18) . ?
C3 C4 1.3838(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3899(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.3843(16) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

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 N2 126.21(10) . . ?
O1 N1 C1 118.28(9) . . ?
N2 N1 C1 115.41(9) . . ?
N1 N2 N3 107.28(9) . . ?
O2 N3 O3 128.79(11) . . ?
O2 N3 N2 114.99(11) . . ?
O3 N3 N2 116.10(10) . . ?
O4 N4 N5 125.61(11) . . ?
O4 N4 C5 118.71(10) . . ?
N5 N4 C5 115.68(10) . . ?
N4 N5 N6 107.20(10) . . ?
O5 N6 O6 128.33(12) . . ?
O5 N6 N5 116.36(11) . . ?
O6 N6 N5 115.15(11) . . ?
C6 C1 C2 123.97(11) . . ?
C6 C1 N1 114.13(10) . . ?
C2 C1 N1 121.88(11) . . ?
C3 C2 C1 115.45(11) . . ?
C3 C2 C7 120.50(11) . . ?
C1 C2 C7 124.02(11) . . ?
C4 C3 C2 122.88(11) . . ?
C4 C3 H3 118.6 . . ?
C2 C3 H3 118.6 . . ?
C3 C4 C5 118.19(11) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C6 C5 C4 122.06(11) . . ?
C6 C5 N4 116.09(10) . . ?
C4 C5 N4 121.77(11) . . ?
C1 C6 C5 117.42(11) . . ?
C1 C6 H6 121.3 . . ?
C5 C6 H6 121.3 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

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 N2 N3 -2.23(15) . . . . ?
C1 N1 N2 N3 -178.53(9) . . . . ?
N1 N2 N3 O2 97.91(11) . . . . ?
N1 N2 N3 O3 -85.85(12) . . . . ?
O4 N4 N5 N6 -3.77(16) . . . . ?
C5 N4 N5 N6 175.45(9) . . . . ?
N4 N5 N6 O5 93.15(13) . . . . ?
N4 N5 N6 O6 -91.08(13) . . . . ?
O1 N1 C1 C6 -43.52(14) . . . . ?
N2 N1 C1 C6 133.09(11) . . . . ?
O1 N1 C1 C2 135.35(12) . . . . ?
N2 N1 C1 C2 -48.04(14) . . . . ?
C6 C1 C2 C3 0.75(17) . . . . ?
N1 C1 C2 C3 -178.00(10) . . . . ?
C6 C1 C2 C7 178.88(11) . . . . ?
N1 C1 C2 C7 0.13(17) . . . . ?
C1 C2 C3 C4 -1.71(18) . . . . ?
C7 C2 C3 C4 -179.91(12) . . . . ?
C2 C3 C4 C5 1.23(19) . . . . ?
C3 C4 C5 C6 0.29(18) . . . . ?
C3 C4 C5 N4 -176.37(11) . . . . ?
O4 N4 C5 C6 -13.56(15) . . . . ?
N5 N4 C5 C6 167.16(10) . . . . ?
O4 N4 C5 C4 163.29(11) . . . . ?
N5 N4 C5 C4 -15.99(16) . . . . ?
C2 C1 C6 C5 0.63(17) . . . . ?
N1 C1 C6 C5 179.47(9) . . . . ?
C4 C5 C6 C1 -1.17(17) . . . . ?
N4 C5 C6 C1 175.66(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        29.13
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.047

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
_database_code_depnum_ccdc_archive 'CCDC 1023014'
#######################################################################
#
#                 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_bo2465

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2,6-dinitro-4-nitro-NNO-azoxytoluene
_chemical_name_common            ?
_chemical_melting_point          387
_chemical_formula_moiety         C7H5N5O7
_chemical_formula_sum            'C7 H5 N5 O7'
_chemical_formula_weight         271.16

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   5.2932(15)
_cell_length_b                   29.236(8)
_cell_length_c                   6.907(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.746(4)
_cell_angle_gamma                90.00
_cell_volume                     1056.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    3669
_cell_measurement_theta_min      2.787
_cell_measurement_theta_max      31.507

_exptl_crystal_description       Chunk
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.9210
_exptl_absorpt_correction_T_max  0.9756
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8887
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         29.00
_reflns_number_total             2800
_reflns_number_gt                2335
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_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)+(0.0695P)²+0.2590P] 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       0.004(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2800
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1290
_refine_ls_wR_factor_gt          0.1185
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
O1 O 0.6341(2) 0.20138(4) 0.87635(16) 0.0331(3) Uani 1 1 d . . .
O2 O 0.1788(3) 0.22976(5) 1.0367(2) 0.0504(4) Uani 1 1 d . . .
O3 O 0.2629(3) 0.28255(5) 0.8325(2) 0.0447(4) Uani 1 1 d . . .
O4 O -0.0255(2) 0.12616(4) 0.11769(17) 0.0323(3) Uani 1 1 d . . .
O5 O 0.2935(3) 0.11005(4) -0.03384(16) 0.0347(3) Uani 1 1 d . . .
O6 O 1.0685(2) 0.04864(4) 0.49207(19) 0.0344(3) Uani 1 1 d . . .
O7 O 0.9078(3) 0.03894(4) 0.76041(18) 0.0373(3) Uani 1 1 d . . .
N1 N 0.4508(2) 0.19138(4) 0.74950(17) 0.0231(3) Uani 1 1 d . . .
N2 N 0.2274(3) 0.20884(5) 0.7279(2) 0.0311(3) Uani 1 1 d . . .
N3 N 0.2268(3) 0.24351(5) 0.8811(2) 0.0333(3) Uani 1 1 d . . .
N4 N 0.2010(3) 0.11795(4) 0.11500(18) 0.0244(3) Uani 1 1 d . . .
N5 N 0.9090(3) 0.05637(4) 0.59936(19) 0.0260(3) Uani 1 1 d . . .
C1 C 0.4835(3) 0.15552(5) 0.6081(2) 0.0215(3) Uani 1 1 d . . .
C2 C 0.3267(3) 0.15368(5) 0.4293(2) 0.0218(3) Uani 1 1 d . . .
H2 H 0.1936 0.1753 0.3942 0.026 Uiso 1 1 calc R . .
C3 C 0.3725(3) 0.11888(5) 0.3036(2) 0.0216(3) Uani 1 1 d . . .
C4 C 0.5583(3) 0.08479(5) 0.3463(2) 0.0223(3) Uani 1 1 d . . .
C5 C 0.7055(3) 0.08976(5) 0.5317(2) 0.0221(3) Uani 1 1 d . . .
C6 C 0.6748(3) 0.12394(5) 0.6632(2) 0.0230(3) Uani 1 1 d . . .
H6 H 0.7810 0.1257 0.7869 0.028 Uiso 1 1 calc R . .
C7 C 0.5818(3) 0.04433(5) 0.2151(2) 0.0294(3) Uani 1 1 d . . .
H7A H 0.6870 0.0527 0.1155 0.035 Uiso 1 1 calc R . .
H7B H 0.4115 0.0351 0.1509 0.035 Uiso 1 1 calc R . .
H7C H 0.6623 0.0188 0.2935 0.035 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0311(6) 0.0393(7) 0.0244(6) -0.0098(5) -0.0103(5) 0.0038(5)
O2 0.0563(9) 0.0610(10) 0.0385(8) -0.0178(7) 0.0220(7) -0.0123(7)
O3 0.0541(9) 0.0348(7) 0.0427(8) -0.0085(6) -0.0012(6) 0.0122(6)
O4 0.0264(6) 0.0420(7) 0.0257(6) 0.0005(5) -0.0048(4) 0.0012(5)
O5 0.0428(7) 0.0444(7) 0.0170(5) -0.0025(5) 0.0047(5) -0.0023(5)
O6 0.0262(6) 0.0318(6) 0.0471(7) 0.0052(5) 0.0114(5) 0.0031(5)
O7 0.0480(8) 0.0353(7) 0.0269(6) 0.0072(5) 0.0004(5) 0.0097(5)
N1 0.0251(6) 0.0260(6) 0.0170(6) -0.0010(5) -0.0008(5) 0.0002(5)
N2 0.0268(7) 0.0370(8) 0.0281(7) -0.0130(6) -0.0004(5) 0.0035(5)
N3 0.0271(7) 0.0413(8) 0.0307(7) -0.0148(6) 0.0017(6) 0.0035(6)
N4 0.0288(7) 0.0254(6) 0.0177(6) 0.0008(5) -0.0008(5) -0.0031(5)
N5 0.0253(7) 0.0233(6) 0.0280(6) 0.0006(5) -0.0006(5) 0.0001(5)
C1 0.0233(7) 0.0241(7) 0.0166(6) -0.0018(5) 0.0015(5) -0.0013(5)
C2 0.0217(7) 0.0242(7) 0.0187(6) 0.0015(5) 0.0002(5) -0.0008(5)
C3 0.0230(7) 0.0263(7) 0.0149(6) 0.0010(5) 0.0006(5) -0.0043(5)
C4 0.0223(7) 0.0248(7) 0.0199(6) 0.0003(5) 0.0033(5) -0.0042(5)
C5 0.0194(7) 0.0242(7) 0.0225(7) 0.0022(5) 0.0023(5) 0.0004(5)
C6 0.0219(7) 0.0281(7) 0.0177(6) 0.0015(5) -0.0011(5) -0.0009(5)
C7 0.0315(8) 0.0275(8) 0.0288(8) -0.0058(6) 0.0031(6) -0.0020(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
O1 N1 1.2391(16) . ?
O2 N3 1.210(2) . ?
O3 N3 1.213(2) . ?
O4 N4 1.2255(18) . ?
O5 N4 1.2262(16) . ?
O6 N5 1.2258(18) . ?
O7 N5 1.2245(17) . ?
N1 N2 1.2758(19) . ?
N1 C1 1.4610(18) . ?
N2 N3 1.4654(18) . ?
N4 C3 1.4704(18) . ?
N5 C5 1.4760(19) . ?
C1 C6 1.380(2) . ?
C1 C2 1.3806(19) . ?
C2 C3 1.383(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.400(2) . ?
C4 C5 1.402(2) . ?
C4 C7 1.507(2) . ?
C5 C6 1.377(2) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

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 N2 126.89(13) . . ?
O1 N1 C1 118.85(12) . . ?
N2 N1 C1 114.26(12) . . ?
N1 N2 N3 107.22(12) . . ?
O2 N3 O3 128.41(15) . . ?
O2 N3 N2 115.79(15) . . ?
O3 N3 N2 115.71(14) . . ?
O4 N4 O5 124.48(13) . . ?
O4 N4 C3 117.18(12) . . ?
O5 N4 C3 118.32(13) . . ?
O7 N5 O6 124.87(14) . . ?
O7 N5 C5 117.29(13) . . ?
O6 N5 C5 117.84(13) . . ?
C6 C1 C2 122.47(14) . . ?
C6 C1 N1 116.88(12) . . ?
C2 C1 N1 120.65(13) . . ?
C1 C2 C3 116.84(14) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 H2 121.6 . . ?
C2 C3 C4 125.19(13) . . ?
C2 C3 N4 115.22(13) . . ?
C4 C3 N4 119.54(13) . . ?
C3 C4 C5 113.20(13) . . ?
C3 C4 C7 123.50(13) . . ?
C5 C4 C7 123.06(14) . . ?
C6 C5 C4 124.97(14) . . ?
C6 C5 N5 115.13(13) . . ?
C4 C5 N5 119.89(13) . . ?
C5 C6 C1 117.30(13) . . ?
C5 C6 H6 121.3 . . ?
C1 C6 H6 121.3 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

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 N2 N3 0.4(2) . . . . ?
C1 N1 N2 N3 179.45(12) . . . . ?
N1 N2 N3 O2 -86.72(18) . . . . ?
N1 N2 N3 O3 96.58(16) . . . . ?
O1 N1 C1 C6 23.3(2) . . . . ?
N2 N1 C1 C6 -155.87(14) . . . . ?
O1 N1 C1 C2 -157.34(14) . . . . ?
N2 N1 C1 C2 23.5(2) . . . . ?
C6 C1 C2 C3 -1.2(2) . . . . ?
N1 C1 C2 C3 179.39(12) . . . . ?
C1 C2 C3 C4 2.3(2) . . . . ?
C1 C2 C3 N4 179.75(12) . . . . ?
O4 N4 C3 C2 -40.30(18) . . . . ?
O5 N4 C3 C2 138.18(14) . . . . ?
O4 N4 C3 C4 137.29(15) . . . . ?
O5 N4 C3 C4 -44.23(19) . . . . ?
C2 C3 C4 C5 -2.0(2) . . . . ?
N4 C3 C4 C5 -179.29(12) . . . . ?
C2 C3 C4 C7 172.51(14) . . . . ?
N4 C3 C4 C7 -4.8(2) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C7 C4 C5 C6 -173.92(14) . . . . ?
C3 C4 C5 N5 179.66(13) . . . . ?
C7 C4 C5 N5 5.2(2) . . . . ?
O7 N5 C5 C6 50.69(19) . . . . ?
O6 N5 C5 C6 -128.26(15) . . . . ?
O7 N5 C5 C4 -128.48(15) . . . . ?
O6 N5 C5 C4 52.56(19) . . . . ?
C4 C5 C6 C1 0.3(2) . . . . ?
N5 C5 C6 C1 -178.81(13) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
N1 C1 C6 C5 179.40(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        29.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.051

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/ethyl acetate'
_database_code_depnum_ccdc_archive 'CCDC 1023015'
