# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

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

data_kx066
_database_code_depnum_ccdc_archive 'CCDC 1420413'
_audit_update_record             
;
2015-08-25 deposited with the CCDC.
2015-11-13 downloaded from the CCDC.
;
_audit_block_code                ?
_audit_creation_method           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_audit_creation_date             05.02.2015

_chemical_name_systematic        1,1,2,2-Tetranitratoethane
_chemical_compound_source        ?
_chemical_name_common            1,1,2,2-Tetranitratoethane
_chemical_formula_moiety         'C2 H2 N4 O12'
_chemical_formula_sum            'C2 H2 N4 O12'
_chemical_formula_weight         274.08


_cell_length_a                   7.5489(4)
_cell_length_b                   7.2995(3)
_cell_length_c                   8.3759(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.935(6)
_cell_angle_gamma                90.00
_cell_volume                     457.12(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173.05(10)
_cell_measurement_reflns_used    821
_cell_measurement_theta_min      4.8000
_cell_measurement_theta_max      32.6680
_cell_special_details            ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.991
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             276
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9149
_exptl_absorpt_correction_T_max  0.9893
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      173 # in K
_diffrn_source_type              'Spellman generator'
_diffrn_source_power             ? # in kW
_diffrn_source_voltage           50 # kV
_diffrn_source_current           40 # mA
_diffrn_radiation_wavelength     0.71073
_diffrn_ambient_environment      N~2~
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_collimation    0.5
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            1801
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.41
_diffrn_reflns_theta_max         27.00
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.994
_cell_oxdiff_twin_number         2

loop_
_cell_oxdiff_twin_id
_cell_oxdiff_twin_matrix_11
_cell_oxdiff_twin_matrix_12
_cell_oxdiff_twin_matrix_13
_cell_oxdiff_twin_matrix_21
_cell_oxdiff_twin_matrix_22
_cell_oxdiff_twin_matrix_23
_cell_oxdiff_twin_matrix_31
_cell_oxdiff_twin_matrix_32
_cell_oxdiff_twin_matrix_33
1 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000 1.0000
2 1.0000 -0.0007 0.2499 0.0000 -1.0001 0.0003 0.0001 0.0003 -1.0001

_diffrn_oxdiff_twin_integration_method simultaneous
loop_
_diffrn_oxdiff_twin_id
_diffrn_oxdiff_twin_ratio
_diffrn_oxdiff_twin_reflns_isolated
_diffrn_oxdiff_twin_reflns_overlapped
1 0.6959 2511 1263
2 0.3041 2516 1263

_reflns_number_total             1801
_reflns_number_gt                1366
_reflns_threshold_expression     >2sigma(I)

_diffrn_orient_matrix_UB_11      0.0628261000
_diffrn_orient_matrix_UB_12      0.0645456000
_diffrn_orient_matrix_UB_13      -0.0215480000
_diffrn_orient_matrix_UB_21      -0.0459161000
_diffrn_orient_matrix_UB_22      0.0023911000
_diffrn_orient_matrix_UB_23      -0.0797918000
_diffrn_orient_matrix_UB_31      -0.0543191000
_diffrn_orient_matrix_UB_32      0.0725853000
_diffrn_orient_matrix_UB_33      0.0218394000



_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  -P2ybc

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'


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

_exptl_special_details           ?


loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?

_diffrn_special_details          ?

_refine_diff_density_max         0.166
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.042

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0406P)²+0.0000P] where P=(Fo²+2Fc²)/3'


_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;

_computing_publication_material  
;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;

_refine_special_details          Twin

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         1801
_refine_ls_number_parameters     87
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0675
_refine_ls_wR_factor_gt          0.0641
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_restrained_S_all      0.945
_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
H1 H 0.3265(13) 0.0168(12) 0.5368(11) 0.019(2) Uiso 1 1 d . . .
O1 O 0.41412(8) 0.20521(8) 0.39786(8) 0.02684(17) Uani 1 1 d . . .
O4 O 0.36814(8) -0.09690(8) 0.33157(8) 0.02691(17) Uani 1 1 d . . .
O2 O 0.21623(9) 0.29574(9) 0.56199(9) 0.03595(19) Uani 1 1 d . . .
O6 O 0.15492(10) -0.21906(10) 0.16210(10) 0.0417(2) Uani 1 1 d . . .
N1 N 0.29819(11) 0.33929(10) 0.45639(10) 0.0280(2) Uani 1 1 d . . .
C1 C 0.40553(12) 0.02567(11) 0.46197(11) 0.0216(2) Uani 1 1 d . . .
N2 N 0.17908(11) -0.11959(11) 0.27570(10) 0.0285(2) Uani 1 1 d . . .
O5 O 0.07756(9) -0.03708(10) 0.34605(9) 0.0406(2) Uani 1 1 d . . .
O3 O 0.30604(11) 0.48120(9) 0.38697(10) 0.0459(2) 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
O1 0.0288(4) 0.0193(3) 0.0331(4) 0.0043(3) 0.0066(3) 0.0037(3)
O4 0.0215(4) 0.0251(4) 0.0327(4) -0.0057(3) -0.0013(3) -0.0001(2)
O2 0.0381(4) 0.0320(4) 0.0387(4) -0.0063(3) 0.0090(4) 0.0058(3)
O6 0.0479(5) 0.0285(4) 0.0438(5) -0.0062(3) -0.0118(4) -0.0070(3)
N1 0.0284(4) 0.0217(4) 0.0314(4) -0.0044(4) -0.0053(4) 0.0043(3)
C1 0.0231(5) 0.0169(4) 0.0251(4) 0.0008(4) 0.0039(4) 0.0003(3)
N2 0.0267(5) 0.0216(4) 0.0347(5) 0.0063(3) -0.0045(4) -0.0037(3)
O5 0.0227(4) 0.0489(5) 0.0493(5) -0.0026(4) 0.0020(3) 0.0009(3)
O3 0.0597(6) 0.0209(4) 0.0560(5) 0.0088(4) 0.0038(4) 0.0099(3)

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 C1 1.4212(11) . ?
O1 N1 1.4431(10) . ?
O4 C1 1.4100(11) . ?
O4 N2 1.4488(10) . ?
O2 N1 1.1904(11) . ?
O6 N2 1.1908(11) . ?
N1 O3 1.1934(10) . ?
C1 C1 1.5264(18) 3_656 ?
C1 H1 0.925(10) . ?
N2 O5 1.1925(11) . ?

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 O1 N1 115.82(7) . . ?
C1 O4 N2 113.93(7) . . ?
O2 N1 O3 131.27(8) . . ?
O2 N1 O1 118.23(7) . . ?
O3 N1 O1 110.48(8) . . ?
O4 C1 O1 107.89(7) . . ?
O4 C1 C1 104.07(9) . 3_656 ?
O1 C1 C1 107.18(9) . 3_656 ?
O4 C1 H1 113.7(6) . . ?
O1 C1 H1 112.8(6) . . ?
C1 C1 H1 110.7(6) 3_656 . ?
O6 N2 O5 131.67(9) . . ?
O6 N2 O4 111.30(8) . . ?
O5 N2 O4 117.02(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
C1 O1 N1 O2 6.13(11) . . . . ?
C1 O1 N1 O3 -175.02(8) . . . . ?
N2 O4 C1 O1 -86.91(8) . . . . ?
N2 O4 C1 C1 159.46(8) . . . 3_656 ?
N1 O1 C1 O4 125.20(7) . . . . ?
N1 O1 C1 C1 -123.26(9) . . . 3_656 ?
C1 O4 N2 O6 177.50(8) . . . . ?
C1 O4 N2 O5 -1.37(10) . . . . ?

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
? ? ? ? ? ? ? ?

_geom_special_details            ?

_iucr_refine_instructions_details 
;
TITL kx066_v1 in P2(1)/c
CELL  0.71073   7.5489   7.2995   8.3759   90.000   97.935   90.000
ZERR     2.00   0.0004   0.0003   0.0008    0.000    0.006    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    O
UNIT  4    4    8    24
MERG   2
OMIT    -2.00  54.00
OMIT     5   4   7
OMIT     6  -1   1
OMIT     6  -1   3
FMAP   2
PLAN   20
SIZE     0.05   0.30   0.42
ACTA
BOND   $H
CONF
L.S.   4
TEMP  -100.00
WGHT    0.040600
BASF   0.27331
FVAR      14.54719
H1    2    0.326523    0.016848    0.536813    11.00000    0.01894
MOLE    1
O1    4    0.414120    0.205215    0.397861    11.00000    0.02878    0.01929 =
         0.03311    0.00435    0.00658    0.00367
O4    4    0.368144   -0.096903    0.331571    11.00000    0.02153    0.02509 =
         0.03270   -0.00569   -0.00128   -0.00007
O2    4    0.216231    0.295745    0.561990    11.00000    0.03811    0.03203 =
         0.03873   -0.00628    0.00896    0.00578
O6    4    0.154920   -0.219058    0.162096    11.00000    0.04786    0.02850 =
         0.04377   -0.00621   -0.01182   -0.00697
N1    3    0.298186    0.339291    0.456393    11.00000    0.02838    0.02169 =
         0.03136   -0.00437   -0.00525    0.00427
C1    1    0.405528    0.025669    0.461971    11.00000    0.02312    0.01685 =
         0.02505    0.00075    0.00394    0.00028
N2    3    0.179084   -0.119585    0.275703    11.00000    0.02671    0.02157 =
         0.03470    0.00633   -0.00451   -0.00371
O5    4    0.077559   -0.037080    0.346054    11.00000    0.02270    0.04893 =
         0.04933   -0.00257    0.00204    0.00094
O3    4    0.306039    0.481200    0.386972    11.00000    0.05967    0.02086 =
         0.05596    0.00884    0.00376    0.00994
HKLF    5
 
REM  kx066_v1 in P2(1)/c
REM R1 =  0.0274 for   1366 Fo > 4sig(Fo)  and  0.0395 for all   1801 data
REM     87 parameters refined using      0 restraints
 
END
 
WGHT      0.0406      0.0000
REM Highest difference peak  0.166,  deepest hole -0.194,  1-sigma level  0.042
Q1    1   0.5000  0.0000  0.5000  10.50000  0.05    0.17
Q2    1   0.1809 -0.3944  0.0805  11.00000  0.05    0.14
Q3    1   0.3989 -0.0914  0.3700  11.00000  0.05    0.14
Q4    1   0.2934  0.0335  0.6057  11.00000  0.05    0.13
Q5    1   0.4123  0.0079  0.1944  11.00000  0.05    0.13
Q6    1   0.3607  0.5855  0.5813  11.00000  0.05    0.13
Q7    1   0.1531 -0.2486  0.1291  11.00000  0.05    0.13
Q8    1   0.1054 -0.1110  0.0559  11.00000  0.05    0.13
Q9    1   0.2167  0.2199  0.3154  11.00000  0.05    0.12
Q10   1   0.2562  0.1885  0.6143  11.00000  0.05    0.12
Q11   1   0.2897 -0.1318  0.3347  11.00000  0.05    0.11
Q12   1   0.4058  0.2487  0.6391  11.00000  0.05    0.11
Q13   1   0.2437  0.4511  0.5854  11.00000  0.05    0.11
Q14   1   0.3472 -0.0993  0.6009  11.00000  0.05    0.11
Q15   1   0.4296  0.0397  0.2733  11.00000  0.05    0.10
Q16   1  -0.0517  0.0443  0.4030  11.00000  0.05    0.10
Q17   1   0.2415 -0.1040  0.1221  11.00000  0.05    0.10
Q18   1   0.3206 -0.0333  0.2602  11.00000  0.05    0.10
Q19   1   0.3169  0.3189  0.5722  11.00000  0.05    0.10
Q20   1   0.3391  0.3729  0.6738  11.00000  0.05    0.10

;
