Energetic materials: variable-temperature crystal structures of γ- and [epsilon]-HNIW polymorphs

Crystals of γ- and [epsilon]-hexanitrohexaazaisowurtzitane (γ- and [epsilon]-HNIW, space group P2₁/n for both crystals) have been investigated in the 100–298 K temperature range using single-crystal X-ray diffraction techniques. Temperature-dependent changes of their crystal lattices have been evaluated from the second-rank thermal expansion tensors. Both lattices undergo anisotropic thermal expansion, that of γ-HNIW being more anisotropic than that of the [epsilon] phase. Comparison with previously reported predictions from molecular dynamics calculations indicates significant differences. Although there are many short (less than van der Waals) intermolecular interactions in both polymorphs, there is no obvious relationship between the short distances and the difference in thermal expansion behavior. Non-linear temperature dependence of the atomic displacement parameters is indicative of anharmon­icity of the crystal mean field potential.

Computing details

For all compounds, data collection: Siemens SMART; cell refinement: Siemens SAINT; data reduction: Siemens SAINT. Program(s) used to solve structure: SHELXS86 (Sheldrick, 1990) for 298gHNIW, 250gHNIW, 200gHNIW, 150gHNIW, 100gHNIW; SHELXS97 (Sheldrick, 1990) for 298eHNIW, 250eHNIW, 200eHNIW, 150eHNIW, 100eHNIW. Program(s) used to refine structure: SHELXL93 (Sheldrick, 1993) for 298gHNIW, 250gHNIW, 200gHNIW, 150gHNIW, 100gHNIW; SHELXL97 (Sheldrick, 1997) for 298eHNIW, 250eHNIW, 200eHNIW, 150eHNIW, 100eHNIW. For all compounds, molecular graphics: Siemens SHELXTL. Software used to prepare material for publication: Siemens SHELXTL and the Toledo cifomatic for 298gHNIW, 250gHNIW, 200gHNIW, 150gHNIW, 100gHNIW; Siemens SHELXTL for 298eHNIW, 250eHNIW, 200eHNIW, 150eHNIW, 100eHNIW.

Figures

(298gHNIW) gamma-hexaizohexaazaisowurtzitane

Crystal data

C6H6N12O12	F(000) = 888
Mr = 438.23	Dx = 1.915 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.2272 (7) Å	Cell parameters from 5732 reflections
b = 8.1692 (5) Å	θ = 3.1–20.4°
c = 14.8920 (8) Å	µ = 0.18 mm^−1
β = 109.164 (1)°	T = 298 K
V = 1520.0 (2) Å^3	Block
Z = 4	0.37 × 0.33 × 0.18 mm

Data collection

Platform diffractometer	3746 independent reflections
Radiation source: Sealed Tube	2671 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
ω scans	θmax = 28.3°, θmin = 2.5°
Absorption correction: empirical :Multipole Expansion Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany	h = −17→7
Tmin = 0.627, Tmax = 0.990	k = −10→10
10300 measured reflections	l = −19→19

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Calculated w = 1/[σ^2(Fo^2) + (0.0607P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.115	(Δ/σ)max = −0.001
S = 1.02	Δρmax = 0.27 e Å^−3
3746 reflections	Δρmin = −0.22 e Å^−3
296 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0127 (15)
Primary atom site location: structure-invariant direct methods

Special details

Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS. No formal measure of the extent of decay is printed out by this program. The final unit cell is obtained from the refinement of the XYZ weighted centroids of reflections above 20 σ(I).

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	1.01349 (11)	0.4574 (2)	0.34558 (8)	0.0285 (3)
C1	1.10707 (13)	0.5134 (2)	0.32341 (10)	0.0286 (3)
H1	1.1698 (15)	0.455 (2)	0.3558 (12)	0.034 (4)*
O1	1.11604 (13)	0.2992 (2)	0.46269 (9)	0.0597 (4)
O2	0.95367 (12)	0.3504 (2)	0.45602 (8)	0.0495 (4)
C2	0.93689 (12)	0.5926 (2)	0.32615 (10)	0.0260 (3)
H2	0.9006 (15)	0.5929 (19)	0.3688 (12)	0.031 (4)*
N2	1.03025 (14)	0.3637 (2)	0.42837 (9)	0.0380 (4)
N3	1.11598 (10)	0.6861 (2)	0.34891 (8)	0.0286 (3)
C3	1.00665 (12)	0.7500 (2)	0.32963 (10)	0.0261 (3)
H3	1.0065 (14)	0.825 (2)	0.3780 (12)	0.031 (4)*
O3	1.18378 (13)	0.8665 (2)	0.46544 (10)	0.0611 (4)
C4	1.08410 (12)	0.5012 (2)	0.21178 (10)	0.0278 (3)
H4	1.1372 (15)	0.437 (2)	0.2000 (11)	0.033 (4)*
O4	1.26246 (12)	0.6317 (2)	0.47409 (10)	0.0634 (4)
N4	1.19287 (12)	0.7302 (2)	0.43760 (10)	0.0412 (4)
N5	0.97052 (11)	0.82907 (14)	0.23881 (8)	0.0295 (3)
C5	0.90143 (13)	0.5741 (2)	0.15363 (10)	0.0257 (3)
H5	0.8471 (14)	0.5608 (18)	0.0980 (11)	0.023 (4)*
O5	0.9853 (2)	1.0716 (2)	0.30754 (11)	0.0832 (6)
C6	0.96894 (13)	0.7334 (2)	0.15718 (10)	0.0265 (3)
H6	0.9407 (13)	0.796 (2)	0.1022 (12)	0.028 (4)*
O6	0.93915 (14)	1.0574 (2)	0.15360 (9)	0.0641 (5)
N6	0.96633 (14)	0.9988 (2)	0.23263 (11)	0.0480 (4)
N7	0.85936 (10)	0.5784 (2)	0.23148 (8)	0.0283 (3)
O7	0.75611 (14)	0.4420 (3)	0.29756 (11)	0.0865 (6)
O8	0.72838 (13)	0.4108 (2)	0.14741 (10)	0.0717 (5)
N8	0.77517 (13)	0.4669 (2)	0.22496 (11)	0.0496 (4)
O9	0.87675 (12)	0.3432 (2)	0.02050 (8)	0.0488 (4)
N9	0.97772 (11)	0.43594 (14)	0.16436 (8)	0.0272 (3)
N10	0.96690 (13)	0.3580 (2)	0.07474 (9)	0.0365 (3)
O10	1.04827 (12)	0.3081 (2)	0.06365 (9)	0.0538 (4)
N11	1.07285 (11)	0.66059 (15)	0.16574 (8)	0.0281 (3)
O11	1.24831 (11)	0.6909 (2)	0.20907 (11)	0.0597 (4)
N12	1.16158 (12)	0.7583 (2)	0.17901 (10)	0.0404 (4)
O12	1.14506 (12)	0.9007 (2)	0.15740 (10)	0.0567 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0341 (7)	0.0303 (7)	0.0225 (6)	0.0030 (5)	0.0111 (5)	0.0049 (5)
C1	0.0261 (8)	0.0355 (8)	0.0235 (7)	0.0054 (7)	0.0073 (6)	0.0018 (6)
O1	0.0704 (11)	0.0606 (9)	0.0406 (7)	0.0185 (8)	0.0079 (7)	0.0218 (6)
O2	0.0736 (10)	0.0457 (7)	0.0390 (7)	−0.0129 (6)	0.0320 (7)	0.0031 (5)
C2	0.0256 (8)	0.0313 (8)	0.0234 (7)	−0.0013 (6)	0.0111 (6)	−0.0009 (5)
N2	0.0606 (11)	0.0301 (7)	0.0228 (6)	−0.0030 (7)	0.0132 (7)	0.0011 (5)
N3	0.0231 (7)	0.0382 (7)	0.0215 (6)	−0.0040 (5)	0.0032 (5)	−0.0044 (5)
C3	0.0280 (8)	0.0266 (7)	0.0241 (7)	−0.0011 (6)	0.0089 (6)	−0.0042 (5)
O3	0.0622 (10)	0.0599 (9)	0.0489 (8)	−0.0188 (7)	0.0017 (7)	−0.0224 (6)
C4	0.0280 (8)	0.0342 (8)	0.0230 (7)	0.0037 (7)	0.0106 (6)	0.0002 (6)
O4	0.0368 (8)	0.0915 (11)	0.0440 (8)	0.0089 (8)	−0.0108 (6)	−0.0067 (7)
N4	0.0310 (8)	0.0612 (10)	0.0270 (7)	−0.0136 (7)	0.0038 (6)	−0.0069 (6)
N5	0.0376 (8)	0.0206 (6)	0.0292 (6)	−0.0001 (5)	0.0094 (6)	0.0005 (4)
C5	0.0256 (8)	0.0272 (7)	0.0216 (7)	−0.0031 (6)	0.0041 (6)	0.0006 (5)
O5	0.155 (2)	0.0293 (7)	0.0565 (9)	−0.0053 (9)	0.0228 (10)	−0.0145 (6)
C6	0.0305 (8)	0.0251 (7)	0.0227 (7)	−0.0029 (6)	0.0072 (6)	0.0016 (5)
O6	0.1053 (14)	0.0298 (7)	0.0538 (8)	0.0049 (7)	0.0217 (9)	0.0143 (6)
N6	0.0676 (11)	0.0239 (7)	0.0500 (9)	−0.0011 (7)	0.0158 (8)	−0.0003 (6)
N7	0.0202 (6)	0.0370 (7)	0.0276 (6)	−0.0063 (5)	0.0079 (5)	−0.0015 (5)
O7	0.0648 (11)	0.148 (2)	0.0541 (9)	−0.0623 (11)	0.0301 (8)	−0.0068 (10)
O8	0.0593 (10)	0.1030 (13)	0.0484 (8)	−0.0524 (9)	0.0118 (7)	−0.0152 (8)
N8	0.0351 (9)	0.0717 (11)	0.0422 (9)	−0.0248 (8)	0.0129 (7)	−0.0040 (7)
O9	0.0596 (9)	0.0513 (8)	0.0287 (6)	−0.0102 (6)	0.0052 (6)	−0.0113 (5)
N9	0.0349 (7)	0.0277 (6)	0.0190 (6)	−0.0015 (5)	0.0090 (5)	−0.0031 (4)
N10	0.0565 (10)	0.0305 (7)	0.0258 (7)	−0.0054 (6)	0.0182 (7)	−0.0028 (5)
O10	0.0632 (10)	0.0624 (9)	0.0457 (7)	0.0010 (7)	0.0315 (7)	−0.0181 (6)
N11	0.0270 (7)	0.0338 (7)	0.0250 (6)	−0.0051 (5)	0.0105 (5)	0.0010 (5)
O11	0.0289 (8)	0.0847 (11)	0.0660 (9)	−0.0088 (7)	0.0161 (7)	0.0029 (8)
N12	0.0366 (9)	0.0537 (10)	0.0343 (8)	−0.0162 (7)	0.0160 (7)	−0.0040 (6)
O12	0.0601 (10)	0.0457 (8)	0.0701 (9)	−0.0222 (7)	0.0293 (8)	−0.0008 (6)

Geometric parameters (Å, º)

N1—N2	1.405 (2)	N5—C6	1.440 (2)
N1—C1	1.456 (2)	C5—N7	1.442 (2)
N1—C2	1.462 (2)	C5—N9	1.487 (2)
C1—N3	1.456 (2)	C5—C6	1.569 (2)
C1—C4	1.592 (2)	O5—N6	1.215 (2)
O1—N2	1.202 (2)	C6—N11	1.464 (2)
O2—N2	1.217 (2)	O6—N6	1.211 (2)
C2—N7	1.450 (2)	N7—N8	1.417 (2)
C2—C3	1.573 (2)	O7—N8	1.205 (2)
N3—N4	1.424 (2)	O8—N8	1.207 (2)
N3—C3	1.474 (2)	O9—N10	1.207 (2)
C3—N5	1.432 (2)	N9—N10	1.443 (2)
O3—N4	1.208 (2)	N10—O10	1.212 (2)
C4—N9	1.453 (2)	N11—N12	1.379 (2)
C4—N11	1.457 (2)	O11—N12	1.218 (2)
O4—N4	1.209 (2)	N12—O12	1.208 (2)
N5—N6	1.390 (2)
N2—N1—C1	117.97 (13)	N7—C5—N9	111.08 (11)
N2—N1—C2	118.98 (12)	N7—C5—C6	108.55 (11)
C1—N1—C2	107.65 (11)	N9—C5—C6	105.50 (12)
N1—C1—N3	104.32 (12)	N5—C6—N11	113.20 (12)
N1—C1—C4	109.40 (12)	N5—C6—C5	109.22 (12)
N3—C1—C4	107.72 (11)	N11—C6—C5	100.00 (11)
N7—C2—N1	110.78 (11)	O6—N6—O5	127.3 (2)
N7—C2—C3	108.50 (11)	O6—N6—N5	116.82 (14)
N1—C2—C3	104.49 (12)	O5—N6—N5	115.82 (14)
O1—N2—O2	126.23 (14)	N8—N7—C5	115.55 (12)
O1—N2—N1	117.82 (15)	N8—N7—C2	114.02 (12)
O2—N2—N1	115.86 (15)	C5—N7—C2	116.57 (12)
N4—N3—C1	117.34 (12)	O7—N8—O8	127.0 (2)
N4—N3—C3	116.58 (12)	O7—N8—N7	115.99 (14)
C1—N3—C3	107.59 (11)	O8—N8—N7	117.00 (14)
N5—C3—N3	110.21 (12)	N10—N9—C4	113.43 (12)
N5—C3—C2	109.10 (12)	N10—N9—C5	112.20 (11)
N3—C3—C2	104.13 (11)	C4—N9—C5	106.78 (11)
N9—C4—N11	99.57 (11)	O9—N10—O10	126.99 (14)
N9—C4—C1	110.67 (12)	O9—N10—N9	116.08 (14)
N11—C4—C1	112.99 (12)	O10—N10—N9	116.85 (14)
O3—N4—O4	127.3 (2)	N12—N11—C4	119.97 (13)
O3—N4—N3	115.50 (15)	N12—N11—C6	120.52 (12)
O4—N4—N3	117.07 (15)	C4—N11—C6	110.61 (11)
N6—N5—C3	120.42 (12)	O12—N12—O11	126.9 (2)
N6—N5—C6	119.79 (12)	O12—N12—N11	116.65 (15)
C3—N5—C6	117.42 (11)	O11—N12—N11	116.46 (15)

(250gHNIW) gamma-hexanitrohexaazaisowurtzitane

Crystal data

C6H6N12O12	F(000) = 888
Mr = 438.23	Dx = 1.929 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.1670 (3) Å	Cell parameters from 6062 reflections
b = 8.1676 (1) Å	θ = 3.1–22.2°
c = 14.8436 (1) Å	µ = 0.19 mm^−1
β = 109.001 (1)°	T = 250 K
V = 1509.34 (4) Å^3	Block
Z = 4	0.37 × 0.33 × 0.18 mm

Data collection

Platform diffractometer	3714 independent reflections
Radiation source: Sealed Tube	2772 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
ω scans	θmax = 28.3°, θmin = 2.5°
Absorption correction: empirical :Multipole Expansion Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany	h = −17→7
Tmin = 0.743, Tmax = 0.990	k = −10→10
10203 measured reflections	l = −19→19

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Calculated w = 1/[σ^2(Fo^2) + (0.0556P)^2 + 0.1184P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.109	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.31 e Å^−3
3714 reflections	Δρmin = −0.22 e Å^−3
296 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0096 (13)
Primary atom site location: structure-invariant direct methods

Special details

Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS. No formal measure of the extent of decay is printed out by this program. The final unit cell is obtained from the refinement of the XYZ weighted centroids of reflections above 20 σ(I).

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	1.10712 (12)	0.5120 (2)	0.32352 (10)	0.0224 (3)
C2	0.93654 (12)	0.5942 (2)	0.32656 (10)	0.0208 (3)
C3	1.00748 (12)	0.7505 (2)	0.32999 (10)	0.0211 (3)
C4	1.08408 (12)	0.4996 (2)	0.21162 (10)	0.0226 (3)
C5	0.90099 (12)	0.5748 (2)	0.15356 (10)	0.0205 (3)
C6	0.96961 (12)	0.7335 (2)	0.15709 (10)	0.0214 (3)
N1	1.01287 (10)	0.45789 (14)	0.34580 (8)	0.0231 (3)
N2	1.02870 (13)	0.3641 (2)	0.42844 (9)	0.0301 (3)
N3	1.11678 (10)	0.68546 (15)	0.34901 (8)	0.0228 (3)
N4	1.19387 (11)	0.7288 (2)	0.43789 (9)	0.0329 (3)
N5	0.97169 (11)	0.82949 (14)	0.23886 (8)	0.0233 (3)
N6	0.96819 (13)	0.9995 (2)	0.23260 (10)	0.0383 (4)
N7	0.85886 (10)	0.58036 (15)	0.23191 (8)	0.0227 (3)
N8	0.77392 (12)	0.4701 (2)	0.22545 (11)	0.0406 (4)
N9	0.97693 (11)	0.43579 (14)	0.16438 (8)	0.0218 (3)
N10	0.96593 (12)	0.3580 (2)	0.07439 (9)	0.0287 (3)
N11	1.07362 (10)	0.65945 (15)	0.16537 (8)	0.0228 (3)
N12	1.16289 (11)	0.7559 (2)	0.17898 (9)	0.0325 (3)
O1	1.11490 (12)	0.2990 (2)	0.46309 (9)	0.0473 (4)
O2	0.95137 (11)	0.35137 (15)	0.45605 (8)	0.0398 (3)
O3	1.18566 (12)	0.8657 (2)	0.46546 (9)	0.0481 (4)
O4	1.26315 (11)	0.6294 (2)	0.47468 (9)	0.0510 (4)
O5	0.9872 (2)	1.0726 (2)	0.30750 (10)	0.0685 (6)
O6	0.94194 (14)	1.05779 (14)	0.15356 (9)	0.0515 (4)
O7	0.75388 (13)	0.4468 (2)	0.29855 (10)	0.0707 (5)
O8	0.72656 (13)	0.4137 (2)	0.14787 (10)	0.0584 (5)
O9	0.87529 (11)	0.34288 (15)	0.02060 (8)	0.0387 (3)
O10	1.04726 (11)	0.3087 (2)	0.06240 (9)	0.0429 (3)
O11	1.24989 (10)	0.6878 (2)	0.20908 (10)	0.0474 (4)
O12	1.14703 (12)	0.8992 (2)	0.15747 (10)	0.0455 (3)
H1	1.1707 (15)	0.452 (2)	0.3554 (12)	0.027 (4)*
H2	0.9007 (14)	0.5964 (19)	0.3689 (12)	0.022 (4)*
H3	1.0077 (14)	0.8239 (19)	0.3789 (12)	0.022 (4)*
H4	1.1382 (15)	0.433 (2)	0.1986 (12)	0.027 (4)*
H5	0.8463 (14)	0.5621 (18)	0.0976 (11)	0.018 (4)*
H6	0.9414 (13)	0.7959 (19)	0.1018 (12)	0.021 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0207 (7)	0.0270 (7)	0.0196 (7)	0.0043 (6)	0.0067 (6)	0.0012 (5)
C2	0.0196 (7)	0.0247 (7)	0.0200 (7)	−0.0016 (6)	0.0090 (6)	−0.0009 (5)
C3	0.0221 (7)	0.0217 (7)	0.0199 (7)	−0.0010 (6)	0.0074 (6)	−0.0023 (5)
C4	0.0238 (8)	0.0255 (7)	0.0193 (7)	0.0019 (6)	0.0082 (6)	−0.0003 (5)
C5	0.0191 (7)	0.0220 (7)	0.0185 (7)	−0.0018 (6)	0.0034 (6)	−0.0002 (5)
C6	0.0239 (8)	0.0206 (7)	0.0187 (7)	−0.0015 (6)	0.0057 (6)	0.0014 (5)
N1	0.0291 (7)	0.0232 (6)	0.0184 (6)	0.0017 (5)	0.0097 (5)	0.0044 (4)
N2	0.0468 (9)	0.0240 (6)	0.0192 (6)	−0.0022 (6)	0.0103 (6)	0.0008 (5)
N3	0.0190 (6)	0.0304 (7)	0.0167 (6)	−0.0036 (5)	0.0027 (5)	−0.0033 (4)
N4	0.0244 (7)	0.0479 (9)	0.0236 (7)	−0.0101 (6)	0.0038 (6)	−0.0054 (6)
N5	0.0297 (7)	0.0148 (6)	0.0244 (6)	0.0002 (5)	0.0076 (5)	0.0003 (4)
N6	0.0540 (10)	0.0186 (6)	0.0407 (8)	−0.0001 (6)	0.0131 (7)	−0.0004 (5)
N7	0.0159 (6)	0.0282 (6)	0.0240 (6)	−0.0040 (5)	0.0067 (5)	−0.0014 (5)
N8	0.0268 (8)	0.0602 (10)	0.0354 (8)	−0.0201 (7)	0.0109 (6)	−0.0026 (7)
N9	0.0280 (7)	0.0211 (6)	0.0166 (6)	−0.0012 (5)	0.0078 (5)	−0.0027 (4)
N10	0.0447 (9)	0.0230 (6)	0.0216 (6)	−0.0036 (6)	0.0153 (6)	−0.0026 (5)
N11	0.0214 (6)	0.0267 (6)	0.0215 (6)	−0.0045 (5)	0.0088 (5)	0.0010 (4)
N12	0.0288 (8)	0.0439 (9)	0.0279 (7)	−0.0124 (6)	0.0134 (6)	−0.0037 (6)
O1	0.0564 (9)	0.0472 (8)	0.0330 (7)	0.0149 (7)	0.0070 (6)	0.0165 (5)
O2	0.0580 (9)	0.0362 (7)	0.0330 (6)	−0.0117 (6)	0.0256 (6)	0.0024 (5)
O3	0.0492 (9)	0.0452 (8)	0.0405 (7)	−0.0148 (6)	0.0017 (6)	−0.0175 (6)
O4	0.0311 (7)	0.0718 (10)	0.0366 (7)	0.0080 (7)	−0.0074 (6)	−0.0051 (6)
O5	0.129 (2)	0.0233 (7)	0.0452 (8)	−0.0028 (8)	0.0181 (9)	−0.0117 (5)
O6	0.0844 (12)	0.0237 (6)	0.0441 (7)	0.0046 (6)	0.0177 (8)	0.0119 (5)
O7	0.0521 (10)	0.1225 (15)	0.0440 (8)	−0.0516 (10)	0.0245 (7)	−0.0065 (8)
O8	0.0481 (9)	0.0840 (11)	0.0400 (8)	−0.0436 (8)	0.0103 (7)	−0.0127 (7)
O9	0.0467 (8)	0.0402 (7)	0.0242 (6)	−0.0085 (6)	0.0046 (6)	−0.0098 (5)
O10	0.0505 (9)	0.0483 (8)	0.0375 (7)	0.0012 (6)	0.0249 (6)	−0.0142 (5)
O11	0.0228 (7)	0.0661 (9)	0.0534 (8)	−0.0077 (6)	0.0123 (6)	0.0025 (7)
O12	0.0481 (9)	0.0355 (7)	0.0578 (8)	−0.0175 (6)	0.0240 (7)	−0.0008 (5)

Geometric parameters (Å, º)

C1—N1	1.453 (2)	N2—O2	1.220 (2)
C1—N3	1.461 (2)	N3—N4	1.423 (2)
C1—C4	1.592 (2)	N4—O3	1.207 (2)
C2—N7	1.448 (2)	N4—O4	1.211 (2)
C2—N1	1.464 (2)	N5—N6	1.392 (2)
C2—C3	1.573 (2)	N6—O6	1.208 (2)
C3—N5	1.433 (2)	N6—O5	1.214 (2)
C3—N3	1.473 (2)	N7—N8	1.415 (2)
C4—N9	1.453 (2)	N8—O8	1.208 (2)
C4—N11	1.460 (2)	N8—O7	1.212 (2)
C5—N7	1.443 (2)	N9—N10	1.443 (2)
C5—N9	1.486 (2)	N10—O9	1.207 (2)
C5—C6	1.571 (2)	N10—O10	1.210 (2)
C6—N5	1.438 (2)	N11—N12	1.374 (2)
C6—N11	1.465 (2)	N12—O12	1.213 (2)
N1—N2	1.403 (2)	N12—O11	1.219 (2)
N2—O1	1.206 (2)
N1—C1—N3	104.16 (11)	O3—N4—O4	127.28 (15)
N1—C1—C4	109.36 (12)	O3—N4—N3	115.42 (14)
N3—C1—C4	107.61 (11)	O4—N4—N3	117.16 (14)
N7—C2—N1	110.66 (11)	N6—N5—C3	120.38 (11)
N7—C2—C3	108.61 (11)	N6—N5—C6	119.78 (11)
N1—C2—C3	104.38 (12)	C3—N5—C6	117.50 (11)
N5—C3—N3	110.12 (11)	O6—N6—O5	127.18 (15)
N5—C3—C2	109.00 (11)	O6—N6—N5	116.81 (13)
N3—C3—C2	104.25 (11)	O5—N6—N5	115.92 (13)
N9—C4—N11	99.54 (11)	N8—N7—C5	115.34 (11)
N9—C4—C1	110.59 (11)	N8—N7—C2	114.12 (12)
N11—C4—C1	113.00 (11)	C5—N7—C2	116.68 (12)
N7—C5—N9	111.02 (11)	O8—N8—O7	126.73 (15)
N7—C5—C6	108.34 (11)	O8—N8—N7	117.31 (13)
N9—C5—C6	105.50 (12)	O7—N8—N7	115.90 (14)
N5—C6—N11	113.20 (12)	N10—N9—C4	113.20 (12)
N5—C6—C5	109.31 (11)	N10—N9—C5	112.02 (11)
N11—C6—C5	100.00 (11)	C4—N9—C5	106.95 (11)
N2—N1—C1	118.04 (12)	O9—N10—O10	126.90 (13)
N2—N1—C2	118.87 (12)	O9—N10—N9	115.91 (13)
C1—N1—C2	107.89 (11)	O10—N10—N9	117.10 (14)
O1—N2—O2	126.28 (14)	N12—N11—C4	119.86 (12)
O1—N2—N1	117.70 (14)	N12—N11—C6	120.48 (12)
O2—N2—N1	115.95 (14)	C4—N11—C6	110.55 (11)
N4—N3—C1	117.20 (12)	O12—N12—O11	126.61 (15)
N4—N3—C3	116.46 (12)	O12—N12—N11	116.65 (14)
C1—N3—C3	107.64 (11)	O11—N12—N11	116.71 (14)

(200gHNIW) gamma-hexanitrohexaazaizowurtzitane

Crystal data

C6H6N12O12	F(000) = 888
Mr = 438.23	Dx = 1.938 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.1156 (7) Å	Cell parameters from 6489 reflections
b = 8.1713 (4) Å	θ = 3.1–26.7°
c = 14.8059 (8) Å	µ = 0.19 mm^−1
β = 108.841 (1)°	T = 200 K
V = 1501.75 (14) Å^3	Block
Z = 4	0.37 × 0.33 × 0.18 mm

Data collection

Platform diffractometer	3686 independent reflections
Radiation source: Sealed Tube	2875 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
ω scans	θmax = 28.3°, θmin = 2.5°
Absorption correction: empirical :Multipole Expansion Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany	h = −17→7
Tmin = 0.737, Tmax = 0.990	k = −10→10
10149 measured reflections	l = −19→19

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Calculated w = 1/[σ^2(Fo^2) + (0.051P)^2 + 0.1409P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.101	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.34 e Å^−3
3686 reflections	Δρmin = −0.24 e Å^−3
296 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0078 (11)
Primary atom site location: structure-invariant direct methods

Special details

Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS. No formal measure of the extent of decay is printed out by this program. The final unit cell is obtained from the refinement of the XYZ weighted centroids of reflections above 20 σ(I).

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	1.10720 (11)	0.5111 (2)	0.32365 (9)	0.0179 (3)
C2	0.93625 (11)	0.5956 (2)	0.32705 (9)	0.0168 (3)
C3	1.00836 (11)	0.7511 (2)	0.33030 (9)	0.0173 (3)
C4	1.08410 (12)	0.4987 (2)	0.21157 (9)	0.0178 (3)
C5	0.90077 (11)	0.5757 (2)	0.15365 (9)	0.0166 (3)
C6	0.97020 (11)	0.7335 (2)	0.15690 (9)	0.0171 (3)
N1	1.01222 (10)	0.45845 (14)	0.34615 (8)	0.0186 (3)
N2	1.02746 (11)	0.36460 (14)	0.42874 (8)	0.0238 (3)
N3	1.11783 (9)	0.68472 (14)	0.34902 (8)	0.0185 (2)
N4	1.19506 (10)	0.7277 (2)	0.43801 (8)	0.0255 (3)
N5	0.97287 (10)	0.83010 (13)	0.23890 (8)	0.0188 (3)
N6	0.96981 (12)	0.99998 (15)	0.23253 (9)	0.0308 (3)
N7	0.85806 (9)	0.58261 (13)	0.23218 (8)	0.0182 (2)
N8	0.77247 (11)	0.4731 (2)	0.22624 (10)	0.0326 (3)
N9	0.97620 (10)	0.43585 (13)	0.16435 (7)	0.0177 (2)
N10	0.96495 (11)	0.35815 (14)	0.07412 (8)	0.0228 (3)
N11	1.07432 (10)	0.65821 (14)	0.16502 (8)	0.0183 (2)
N12	1.16436 (10)	0.7536 (2)	0.17904 (8)	0.0257 (3)
O1	1.11373 (11)	0.29824 (15)	0.46342 (8)	0.0371 (3)
O2	0.94947 (10)	0.35243 (13)	0.45625 (7)	0.0315 (3)
O3	1.18758 (11)	0.86525 (15)	0.46553 (8)	0.0384 (3)
O4	1.26401 (10)	0.6273 (2)	0.47512 (8)	0.0400 (3)
O5	0.98885 (15)	1.07368 (14)	0.30776 (9)	0.0535 (4)
O6	0.94454 (12)	1.05803 (13)	0.15316 (8)	0.0405 (3)
O7	0.75175 (11)	0.4517 (2)	0.29931 (9)	0.0561 (4)
O8	0.72508 (11)	0.4161 (2)	0.14838 (9)	0.0468 (4)
O9	0.87372 (10)	0.34231 (13)	0.02086 (7)	0.0306 (3)
O10	1.04669 (10)	0.30949 (14)	0.06142 (8)	0.0339 (3)
O11	1.25148 (9)	0.6851 (2)	0.20917 (9)	0.0377 (3)
O12	1.14891 (10)	0.89760 (14)	0.15769 (8)	0.0352 (3)
H1	1.1713 (14)	0.4526 (19)	0.3563 (11)	0.018 (4)*
H2	0.8996 (14)	0.6011 (18)	0.3708 (11)	0.019 (4)*
H3	1.0088 (14)	0.827 (2)	0.3782 (12)	0.026 (4)*
H4	1.1379 (14)	0.4329 (19)	0.2004 (11)	0.018 (4)*
H5	0.8437 (14)	0.5633 (18)	0.0976 (11)	0.017 (4)*
H6	0.9434 (12)	0.7964 (18)	0.1026 (11)	0.015 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0166 (7)	0.0207 (7)	0.0165 (6)	0.0031 (5)	0.0055 (5)	0.0007 (5)
C2	0.0157 (7)	0.0201 (6)	0.0159 (6)	−0.0014 (5)	0.0069 (5)	−0.0007 (4)
C3	0.0177 (7)	0.0170 (6)	0.0178 (6)	−0.0005 (5)	0.0064 (5)	−0.0020 (5)
C4	0.0183 (7)	0.0209 (7)	0.0149 (6)	0.0019 (5)	0.0065 (5)	−0.0002 (5)
C5	0.0150 (7)	0.0187 (6)	0.0151 (6)	−0.0017 (5)	0.0036 (5)	0.0001 (4)
C6	0.0190 (7)	0.0164 (6)	0.0153 (6)	−0.0013 (5)	0.0046 (5)	0.0011 (5)
N1	0.0229 (6)	0.0191 (6)	0.0157 (5)	0.0017 (5)	0.0088 (5)	0.0034 (4)
N2	0.0371 (8)	0.0188 (6)	0.0153 (6)	−0.0019 (5)	0.0082 (5)	0.0003 (4)
N3	0.0151 (6)	0.0240 (6)	0.0146 (5)	−0.0025 (5)	0.0022 (4)	−0.0033 (4)
N4	0.0180 (6)	0.0369 (7)	0.0193 (6)	−0.0066 (5)	0.0029 (5)	−0.0036 (5)
N5	0.0244 (6)	0.0126 (5)	0.0189 (6)	0.0005 (4)	0.0060 (5)	0.0004 (4)
N6	0.0426 (8)	0.0152 (6)	0.0333 (7)	0.0001 (6)	0.0103 (6)	−0.0003 (5)
N7	0.0128 (6)	0.0236 (6)	0.0188 (6)	−0.0036 (4)	0.0058 (5)	−0.0013 (4)
N8	0.0223 (7)	0.0475 (8)	0.0286 (7)	−0.0155 (6)	0.0088 (6)	−0.0019 (6)
N9	0.0230 (6)	0.0174 (5)	0.0137 (5)	−0.0004 (5)	0.0072 (5)	−0.0027 (4)
N10	0.0353 (8)	0.0187 (6)	0.0166 (6)	−0.0034 (5)	0.0115 (5)	−0.0016 (4)
N11	0.0167 (6)	0.0222 (6)	0.0171 (5)	−0.0033 (5)	0.0072 (4)	0.0009 (4)
N12	0.0227 (7)	0.0343 (7)	0.0223 (6)	−0.0094 (5)	0.0101 (5)	−0.0028 (5)
O1	0.0453 (8)	0.0366 (6)	0.0257 (6)	0.0112 (6)	0.0064 (5)	0.0120 (5)
O2	0.0448 (8)	0.0297 (6)	0.0263 (6)	−0.0089 (5)	0.0201 (5)	0.0015 (4)
O3	0.0386 (8)	0.0362 (7)	0.0330 (6)	−0.0105 (5)	0.0013 (5)	−0.0132 (5)
O4	0.0245 (6)	0.0557 (8)	0.0299 (6)	0.0066 (6)	−0.0049 (5)	−0.0033 (5)
O5	0.1003 (13)	0.0196 (6)	0.0352 (7)	−0.0021 (6)	0.0143 (7)	−0.0087 (5)
O6	0.0652 (10)	0.0207 (6)	0.0340 (6)	0.0027 (6)	0.0136 (6)	0.0094 (4)
O7	0.0398 (8)	0.0994 (12)	0.0343 (7)	−0.0389 (8)	0.0190 (6)	−0.0051 (7)
O8	0.0387 (8)	0.0665 (9)	0.0325 (7)	−0.0342 (7)	0.0077 (6)	−0.0108 (6)
O9	0.0364 (7)	0.0314 (6)	0.0198 (5)	−0.0067 (5)	0.0031 (5)	−0.0074 (4)
O10	0.0391 (7)	0.0383 (6)	0.0303 (6)	0.0010 (5)	0.0194 (5)	−0.0106 (5)
O11	0.0183 (6)	0.0515 (8)	0.0434 (7)	−0.0048 (5)	0.0104 (5)	0.0022 (5)
O12	0.0375 (7)	0.0281 (6)	0.0439 (7)	−0.0129 (5)	0.0184 (6)	−0.0003 (5)

Geometric parameters (Å, º)

C1—N1	1.455 (2)	N2—O2	1.221 (2)
C1—N3	1.462 (2)	N3—N4	1.422 (2)
C1—C4	1.591 (2)	N4—O3	1.211 (2)
C2—N7	1.451 (2)	N4—O4	1.213 (2)
C2—N1	1.465 (2)	N5—N6	1.391 (2)
C2—C3	1.576 (2)	N6—O6	1.210 (2)
C3—N5	1.434 (2)	N6—O5	1.219 (2)
C3—N3	1.475 (2)	N7—N8	1.416 (2)
C4—N9	1.455 (2)	N8—O7	1.210 (2)
C4—N11	1.460 (2)	N8—O8	1.212 (2)
C5—N7	1.446 (2)	N9—N10	1.4431 (15)
C5—N9	1.486 (2)	N10—O9	1.209 (2)
C5—C6	1.570 (2)	N10—O10	1.214 (2)
C6—N5	1.439 (2)	N11—N12	1.373 (2)
C6—N11	1.467 (2)	N12—O12	1.218 (2)
N1—N2	1.402 (2)	N12—O11	1.220 (2)
N2—O1	1.209 (2)
N1—C1—N3	104.23 (10)	O3—N4—O4	127.24 (13)
N1—C1—C4	109.35 (11)	O3—N4—N3	115.46 (12)
N3—C1—C4	107.45 (10)	O4—N4—N3	117.16 (12)
N7—C2—N1	110.77 (10)	N6—N5—C3	120.41 (11)
N7—C2—C3	108.56 (10)	N6—N5—C6	119.86 (10)
N1—C2—C3	104.30 (11)	C3—N5—C6	117.47 (10)
N5—C3—N3	110.02 (11)	O6—N6—O5	127.21 (13)
N5—C3—C2	108.98 (11)	O6—N6—N5	116.74 (12)
N3—C3—C2	104.31 (10)	O5—N6—N5	115.99 (12)
N9—C4—N11	99.49 (10)	N8—N7—C5	115.51 (11)
N9—C4—C1	110.60 (11)	N8—N7—C2	113.88 (11)
N11—C4—C1	113.18 (10)	C5—N7—C2	116.43 (11)
N7—C5—N9	111.22 (10)	O7—N8—O8	126.89 (14)
N7—C5—C6	108.35 (10)	O7—N8—N7	115.99 (12)
N9—C5—C6	105.58 (11)	O8—N8—N7	117.05 (12)
N5—C6—N11	113.11 (11)	N10—N9—C4	113.14 (11)
N5—C6—C5	109.39 (11)	N10—N9—C5	111.97 (10)
N11—C6—C5	99.99 (10)	C4—N9—C5	106.87 (10)
N2—N1—C1	118.05 (11)	O9—N10—O10	126.99 (12)
N2—N1—C2	118.90 (11)	O9—N10—N9	115.77 (12)
C1—N1—C2	107.98 (10)	O10—N10—N9	117.15 (12)
O1—N2—O2	126.26 (12)	N12—N11—C4	119.66 (11)
O1—N2—N1	117.77 (12)	N12—N11—C6	120.44 (11)
O2—N2—N1	115.89 (13)	C4—N11—C6	110.52 (10)
N4—N3—C1	117.22 (11)	O12—N12—O11	126.54 (13)
N4—N3—C3	116.23 (11)	O12—N12—N11	116.48 (13)
C1—N3—C3	107.60 (10)	O11—N12—N11	116.94 (12)

(150gHNIW) gamma-hexanitrohaxaazaisowurtzitane

Crystal data

C6H6N12O12	F(000) = 888
Mr = 438.23	Dx = 1.947 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.0698 (4) Å	Cell parameters from 6836 reflections
b = 8.1737 (3) Å	θ = 3.1–26.7°
c = 14.7718 (5) Å	µ = 0.19 mm^−1
β = 108.696 (1)°	T = 150 K
V = 1494.78 (9) Å^3	Block
Z = 4	0.37 × 0.33 × 0.18 mm

Data collection

Platform diffractometer	3678 independent reflections
Radiation source: Sealed Tube	2981 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω scans	θmax = 28.3°, θmin = 2.5°
Absorption correction: empirical :Multipole Expansion Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany	h = −17→7
Tmin = 0.776, Tmax = 0.990	k = −10→10
10088 measured reflections	l = −19→19

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Calculated w = 1/[σ^2(Fo^2) + (0.0493P)^2 + 0.1643P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.095	(Δ/σ)max = −0.001
S = 1.04	Δρmax = 0.32 e Å^−3
3678 reflections	Δρmin = −0.26 e Å^−3
296 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0074 (11)
Primary atom site location: structure-invariant direct methods

Special details

Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS. No formal measure of the extent of decay is printed out by this program. The final unit cell is obtained from the refinement of the XYZ weighted centroids of reflections above 20 σ(I).

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	1.10726 (11)	0.5103 (2)	0.32378 (9)	0.0142 (3)
C2	0.93615 (11)	0.59724 (15)	0.32746 (9)	0.0136 (3)
C3	1.00915 (11)	0.75182 (15)	0.33048 (9)	0.0139 (3)
C4	1.08430 (11)	0.49759 (15)	0.21156 (9)	0.0143 (3)
C5	0.90041 (11)	0.57671 (15)	0.15361 (9)	0.0136 (3)
C6	0.97084 (11)	0.73366 (15)	0.15673 (9)	0.0139 (3)
N1	1.01165 (9)	0.45888 (13)	0.34637 (7)	0.0148 (2)
N2	1.02649 (10)	0.36479 (13)	0.42896 (8)	0.0187 (3)
N3	1.11873 (9)	0.68410 (13)	0.34911 (7)	0.0149 (2)
N4	1.19613 (9)	0.72646 (15)	0.43823 (8)	0.0197 (3)
N5	0.97397 (9)	0.83042 (12)	0.23902 (7)	0.0150 (2)
N6	0.97140 (11)	1.00083 (14)	0.23260 (9)	0.0235 (3)
N7	0.85770 (9)	0.58446 (13)	0.23261 (7)	0.0146 (2)
N8	0.77116 (10)	0.4758 (2)	0.22663 (9)	0.0250 (3)
N9	0.97559 (9)	0.43555 (13)	0.16437 (7)	0.0142 (2)
N10	0.96409 (10)	0.35832 (13)	0.07394 (7)	0.0178 (2)
N11	1.07511 (9)	0.65711 (13)	0.16477 (7)	0.0145 (2)
N12	1.16552 (10)	0.75212 (14)	0.17898 (8)	0.0196 (3)
O1	1.11291 (9)	0.29777 (13)	0.46367 (7)	0.0280 (3)
O2	0.94769 (9)	0.35343 (12)	0.45644 (7)	0.0241 (2)
O3	1.18930 (9)	0.86484 (13)	0.46548 (7)	0.0294 (3)
O4	1.26482 (9)	0.62540 (14)	0.47553 (7)	0.0300 (3)
O5	0.99010 (13)	1.07447 (13)	0.30782 (8)	0.0405 (3)
O6	0.94683 (10)	1.05842 (12)	0.15298 (7)	0.0307 (3)
O7	0.75003 (10)	0.4560 (2)	0.30015 (8)	0.0428 (3)
O8	0.72381 (10)	0.41806 (15)	0.14881 (8)	0.0355 (3)
O9	0.87237 (9)	0.34196 (12)	0.02101 (7)	0.0239 (2)
O10	1.04614 (9)	0.31042 (13)	0.06036 (7)	0.0258 (2)
O11	1.25286 (8)	0.68271 (14)	0.20910 (8)	0.0288 (3)
O12	1.15046 (9)	0.89649 (12)	0.15786 (8)	0.0270 (3)
H1	1.1714 (13)	0.4487 (18)	0.3565 (11)	0.016 (4)*
H2	0.8981 (13)	0.6033 (18)	0.3717 (11)	0.016 (4)*
H3	1.0101 (13)	0.8252 (18)	0.3785 (11)	0.016 (4)*
H4	1.1383 (13)	0.4288 (18)	0.1998 (10)	0.015 (4)*
H5	0.8442 (13)	0.5661 (17)	0.0961 (11)	0.012 (4)*
H6	0.9455 (12)	0.7951 (18)	0.1022 (11)	0.013 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0137 (6)	0.0167 (6)	0.0126 (6)	0.0022 (5)	0.0048 (5)	0.0009 (4)
C2	0.0131 (6)	0.0152 (6)	0.0133 (6)	−0.0005 (5)	0.0053 (5)	−0.0005 (4)
C3	0.0141 (6)	0.0142 (6)	0.0138 (6)	−0.0007 (5)	0.0051 (5)	−0.0010 (4)
C4	0.0152 (6)	0.0158 (6)	0.0125 (6)	0.0010 (5)	0.0055 (5)	0.0001 (4)
C5	0.0135 (6)	0.0151 (6)	0.0118 (6)	−0.0011 (5)	0.0034 (5)	−0.0002 (4)
C6	0.0148 (6)	0.0144 (6)	0.0122 (6)	−0.0011 (5)	0.0040 (5)	0.0008 (4)
N1	0.0171 (6)	0.0154 (5)	0.0130 (5)	0.0014 (4)	0.0063 (4)	0.0029 (4)
N2	0.0284 (7)	0.0152 (5)	0.0125 (5)	−0.0016 (5)	0.0068 (5)	−0.0002 (4)
N3	0.0122 (5)	0.0187 (5)	0.0120 (5)	−0.0019 (4)	0.0015 (4)	−0.0024 (4)
N4	0.0146 (6)	0.0283 (6)	0.0151 (5)	−0.0054 (5)	0.0030 (4)	−0.0021 (4)
N5	0.0202 (6)	0.0096 (5)	0.0149 (5)	0.0001 (4)	0.0053 (4)	0.0004 (4)
N6	0.0323 (7)	0.0118 (5)	0.0254 (6)	−0.0003 (5)	0.0078 (5)	−0.0003 (4)
N7	0.0106 (5)	0.0188 (5)	0.0149 (5)	−0.0037 (4)	0.0049 (4)	−0.0012 (4)
N8	0.0173 (6)	0.0359 (7)	0.0220 (6)	−0.0109 (5)	0.0064 (5)	−0.0015 (5)
N9	0.0178 (6)	0.0148 (5)	0.0105 (5)	0.0002 (4)	0.0053 (4)	−0.0018 (4)
N10	0.0277 (7)	0.0150 (5)	0.0123 (5)	−0.0028 (5)	0.0085 (5)	−0.0012 (4)
N11	0.0140 (5)	0.0167 (5)	0.0134 (5)	−0.0026 (4)	0.0052 (4)	0.0006 (4)
N12	0.0176 (6)	0.0266 (6)	0.0164 (5)	−0.0069 (5)	0.0077 (5)	−0.0018 (4)
O1	0.0340 (6)	0.0273 (5)	0.0201 (5)	0.0086 (5)	0.0049 (5)	0.0083 (4)
O2	0.0335 (6)	0.0236 (5)	0.0202 (5)	−0.0071 (4)	0.0154 (5)	0.0009 (4)
O3	0.0295 (6)	0.0280 (6)	0.0258 (5)	−0.0081 (5)	0.0022 (5)	−0.0097 (4)
O4	0.0196 (6)	0.0414 (6)	0.0223 (5)	0.0049 (5)	−0.0029 (4)	−0.0017 (4)
O5	0.0740 (10)	0.0160 (5)	0.0273 (6)	−0.0016 (5)	0.0102 (6)	−0.0078 (4)
O6	0.0488 (8)	0.0164 (5)	0.0257 (6)	0.0022 (5)	0.0104 (5)	0.0072 (4)
O7	0.0321 (7)	0.0741 (9)	0.0265 (6)	−0.0284 (7)	0.0156 (5)	−0.0038 (6)
O8	0.0292 (6)	0.0503 (7)	0.0251 (6)	−0.0244 (5)	0.0061 (5)	−0.0077 (5)
O9	0.0280 (6)	0.0247 (5)	0.0161 (5)	−0.0053 (4)	0.0031 (4)	−0.0050 (4)
O10	0.0294 (6)	0.0300 (6)	0.0227 (5)	0.0009 (5)	0.0151 (5)	−0.0076 (4)
O11	0.0152 (5)	0.0385 (6)	0.0326 (6)	−0.0020 (5)	0.0075 (4)	0.0022 (5)
O12	0.0286 (6)	0.0217 (5)	0.0334 (6)	−0.0093 (4)	0.0137 (5)	−0.0002 (4)

Geometric parameters (Å, º)

C1—N1	1.455 (2)	N2—O2	1.226 (2)
C1—N3	1.464 (2)	N3—N4	1.422 (2)
C1—C4	1.591 (2)	N4—O3	1.213 (2)
C2—N7	1.451 (2)	N4—O4	1.214 (2)
C2—N1	1.468 (2)	N5—N6	1.3958 (15)
C2—C3	1.575 (2)	N6—O6	1.211 (2)
C3—N5	1.432 (2)	N6—O5	1.218 (2)
C3—N3	1.477 (2)	N7—N8	1.419 (2)
C4—N9	1.458 (2)	N8—O8	1.213 (2)
C4—N11	1.463 (2)	N8—O7	1.214 (2)
C5—N7	1.447 (2)	N9—N10	1.4411 (14)
C5—N9	1.491 (2)	N10—O9	1.210 (2)
C5—C6	1.571 (2)	N10—O10	1.217 (2)
C6—N5	1.440 (2)	N11—N12	1.373 (2)
C6—N11	1.469 (2)	N12—O12	1.220 (2)
N1—N2	1.4021 (14)	N12—O11	1.224 (2)
N2—O1	1.211 (2)
N1—C1—N3	104.28 (10)	O3—N4—O4	127.29 (12)
N1—C1—C4	109.34 (10)	O3—N4—N3	115.34 (11)
N3—C1—C4	107.42 (9)	O4—N4—N3	117.22 (11)
N7—C2—N1	110.62 (10)	N6—N5—C3	120.35 (10)
N7—C2—C3	108.61 (10)	N6—N5—C6	119.82 (10)
N1—C2—C3	104.38 (10)	C3—N5—C6	117.62 (10)
N5—C3—N3	110.06 (10)	O6—N6—O5	127.41 (12)
N5—C3—C2	108.95 (10)	O6—N6—N5	116.56 (11)
N3—C3—C2	104.31 (10)	O5—N6—N5	115.97 (11)
N9—C4—N11	99.46 (10)	N8—N7—C5	115.36 (10)
N9—C4—C1	110.51 (10)	N8—N7—C2	114.06 (10)
N11—C4—C1	113.19 (10)	C5—N7—C2	116.50 (10)
N7—C5—N9	111.06 (10)	O8—N8—O7	127.07 (13)
N7—C5—C6	108.32 (10)	O8—N8—N7	117.19 (11)
N9—C5—C6	105.60 (10)	O7—N8—N7	115.67 (11)
N5—C6—N11	113.02 (10)	N10—N9—C4	113.05 (10)
N5—C6—C5	109.34 (10)	N10—N9—C5	111.77 (10)
N11—C6—C5	100.03 (9)	C4—N9—C5	106.84 (10)
N2—N1—C1	117.94 (11)	O9—N10—O10	126.91 (11)
N2—N1—C2	119.04 (10)	O9—N10—N9	115.75 (11)
C1—N1—C2	107.96 (10)	O10—N10—N9	117.25 (11)
O1—N2—O2	126.45 (11)	N12—N11—C4	119.73 (11)
O1—N2—N1	117.81 (11)	N12—N11—C6	120.14 (10)
O2—N2—N1	115.66 (11)	C4—N11—C6	110.57 (10)
N4—N3—C1	117.18 (10)	O12—N12—O11	126.62 (12)
N4—N3—C3	116.16 (10)	O12—N12—N11	116.59 (12)
C1—N3—C3	107.60 (10)	O11—N12—N11	116.76 (11)

(100gHNIW) gamma-hexanitrohaxaazaisowurtzitane

Crystal data

C6H6N12O12	F(000) = 888
Mr = 438.23	Dx = 1.954 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.0342 (3) Å	Cell parameters from 7099 reflections
b = 8.1773 (2) Å	θ = 3.1–26.7°
c = 14.7465 (2) Å	µ = 0.19 mm^−1
β = 108.566 (1)°	T = 100 K
V = 1489.95 (5) Å^3	Block
Z = 4	0.37 × 0.33 × 0.18 mm

Data collection

Platform diffractometer	3658 independent reflections
Radiation source: Sealed Tube	3005 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
ω scans	θmax = 28.3°, θmin = 2.5°
Absorption correction: empirical :Multipole Expansion Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany	h = −17→7
Tmin = 0.772, Tmax = 0.990	k = −10→10
9973 measured reflections	l = −19→19

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Calculated w = 1/[σ^2(Fo^2) + (0.0525P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.093	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.38 e Å^−3
3658 reflections	Δρmin = −0.28 e Å^−3
296 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0083 (11)
Primary atom site location: structure-invariant direct methods

Special details

Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS. No formal measure of the extent of decay is printed out by this program. The final unit cell is obtained from the refinement of the XYZ weighted centroids of reflections above 20 σ(I).

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	1.10727 (11)	0.50974 (14)	0.32381 (8)	0.0105 (2)
C2	0.93592 (10)	0.59834 (14)	0.32778 (8)	0.0100 (2)
C3	1.00962 (10)	0.75247 (14)	0.33073 (8)	0.0099 (2)
C4	1.08423 (11)	0.49692 (14)	0.21143 (8)	0.0104 (2)
C5	0.90035 (11)	0.57728 (14)	0.15385 (9)	0.0100 (2)
C6	0.97135 (10)	0.73394 (14)	0.15666 (8)	0.0100 (2)
N1	1.01135 (9)	0.45952 (12)	0.34664 (7)	0.0111 (2)
N2	1.02541 (10)	0.36499 (13)	0.42906 (7)	0.0133 (2)
N3	1.11940 (9)	0.68354 (12)	0.34915 (7)	0.0105 (2)
N4	1.19704 (9)	0.72571 (13)	0.43841 (7)	0.0138 (2)
N5	0.97493 (9)	0.83092 (12)	0.23918 (7)	0.0107 (2)
N6	0.97257 (10)	1.00135 (13)	0.23254 (8)	0.0165 (2)
N7	0.85735 (9)	0.58604 (12)	0.23289 (7)	0.0110 (2)
N8	0.77013 (9)	0.47805 (14)	0.22725 (8)	0.0171 (2)
N9	0.97526 (9)	0.43563 (12)	0.16447 (7)	0.0102 (2)
N10	0.96331 (9)	0.35854 (12)	0.07362 (7)	0.0125 (2)
N11	1.07558 (9)	0.65640 (12)	0.16451 (7)	0.0105 (2)
N12	1.16654 (9)	0.75069 (13)	0.17876 (7)	0.0138 (2)
O1	1.11202 (9)	0.29716 (12)	0.46395 (7)	0.0198 (2)
O2	0.94622 (8)	0.35409 (11)	0.45655 (6)	0.0171 (2)
O3	1.19055 (9)	0.86472 (12)	0.46543 (7)	0.0206 (2)
O4	1.26541 (8)	0.62406 (12)	0.47593 (7)	0.0212 (2)
O5	0.99071 (11)	1.07556 (12)	0.30786 (7)	0.0282 (3)
O6	0.94865 (9)	1.05874 (11)	0.15268 (7)	0.0215 (2)
O7	0.74863 (9)	0.45946 (15)	0.30095 (7)	0.0294 (3)
O8	0.72269 (9)	0.41955 (13)	0.14925 (7)	0.0247 (2)
O9	0.87133 (8)	0.34172 (11)	0.02114 (6)	0.0168 (2)
O10	1.04581 (8)	0.31104 (12)	0.05955 (6)	0.0182 (2)
O11	1.25407 (8)	0.68108 (12)	0.20910 (7)	0.0202 (2)
O12	1.15173 (8)	0.89558 (11)	0.15797 (7)	0.0188 (2)
H1	1.1707 (13)	0.4509 (18)	0.3561 (10)	0.012 (4)*
H2	0.9008 (13)	0.6025 (17)	0.3731 (11)	0.012 (4)*
H3	1.0112 (12)	0.8277 (18)	0.3802 (11)	0.012 (4)*
H4	1.1377 (13)	0.4298 (18)	0.1997 (10)	0.011 (4)*
H5	0.8460 (13)	0.5697 (17)	0.0968 (10)	0.008 (3)*
H6	0.9426 (12)	0.7980 (17)	0.1008 (10)	0.007 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0101 (6)	0.0116 (6)	0.0106 (6)	0.0009 (5)	0.0042 (5)	0.0004 (4)
C2	0.0096 (6)	0.0113 (6)	0.0097 (6)	0.0004 (4)	0.0041 (5)	0.0003 (4)
C3	0.0098 (6)	0.0096 (5)	0.0105 (6)	−0.0004 (4)	0.0036 (5)	−0.0005 (4)
C4	0.0112 (6)	0.0114 (6)	0.0097 (6)	0.0008 (5)	0.0046 (5)	0.0005 (4)
C5	0.0096 (6)	0.0112 (5)	0.0090 (6)	0.0000 (4)	0.0027 (5)	0.0004 (4)
C6	0.0107 (6)	0.0098 (5)	0.0094 (5)	−0.0006 (4)	0.0030 (5)	−0.0003 (4)
N1	0.0124 (6)	0.0121 (5)	0.0100 (5)	0.0014 (4)	0.0051 (4)	0.0025 (4)
N2	0.0198 (6)	0.0112 (5)	0.0091 (5)	−0.0014 (4)	0.0048 (4)	−0.0009 (4)
N3	0.0085 (5)	0.0126 (5)	0.0087 (5)	−0.0012 (4)	0.0006 (4)	−0.0015 (3)
N4	0.0100 (5)	0.0198 (5)	0.0111 (5)	−0.0039 (4)	0.0025 (4)	−0.0018 (4)
N5	0.0152 (6)	0.0062 (5)	0.0108 (5)	0.0007 (4)	0.0041 (4)	0.0006 (3)
N6	0.0218 (6)	0.0093 (5)	0.0182 (6)	0.0000 (4)	0.0061 (5)	−0.0004 (4)
N7	0.0081 (5)	0.0142 (5)	0.0110 (5)	−0.0028 (4)	0.0037 (4)	−0.0009 (4)
N8	0.0113 (6)	0.0241 (6)	0.0162 (5)	−0.0061 (5)	0.0047 (4)	−0.0004 (4)
N9	0.0122 (6)	0.0104 (5)	0.0085 (5)	−0.0001 (4)	0.0039 (4)	−0.0019 (3)
N10	0.0187 (6)	0.0101 (5)	0.0097 (5)	−0.0020 (4)	0.0060 (4)	−0.0007 (4)
N11	0.0087 (5)	0.0118 (5)	0.0115 (5)	−0.0012 (4)	0.0040 (4)	0.0009 (4)
N12	0.0122 (6)	0.0188 (5)	0.0115 (5)	−0.0043 (4)	0.0054 (4)	−0.0018 (4)
O1	0.0227 (6)	0.0203 (5)	0.0146 (5)	0.0058 (4)	0.0035 (4)	0.0049 (4)
O2	0.0219 (6)	0.0175 (5)	0.0153 (5)	−0.0047 (4)	0.0108 (4)	0.0002 (3)
O3	0.0204 (6)	0.0190 (5)	0.0192 (5)	−0.0055 (4)	0.0020 (4)	−0.0068 (4)
O4	0.0135 (5)	0.0284 (5)	0.0170 (5)	0.0040 (4)	−0.0017 (4)	−0.0002 (4)
O5	0.0502 (8)	0.0119 (5)	0.0194 (5)	−0.0012 (5)	0.0069 (5)	−0.0054 (3)
O6	0.0333 (6)	0.0126 (5)	0.0182 (5)	0.0018 (4)	0.0075 (4)	0.0055 (3)
O7	0.0215 (6)	0.0515 (7)	0.0184 (5)	−0.0178 (5)	0.0108 (4)	−0.0021 (5)
O8	0.0207 (6)	0.0345 (6)	0.0173 (5)	−0.0161 (5)	0.0037 (4)	−0.0055 (4)
O9	0.0188 (5)	0.0173 (5)	0.0123 (4)	−0.0040 (4)	0.0021 (4)	−0.0032 (3)
O10	0.0202 (6)	0.0209 (5)	0.0169 (5)	0.0012 (4)	0.0105 (4)	−0.0047 (3)
O11	0.0099 (5)	0.0273 (5)	0.0234 (5)	−0.0006 (4)	0.0054 (4)	0.0020 (4)
O12	0.0206 (6)	0.0141 (5)	0.0236 (5)	−0.0060 (4)	0.0096 (4)	0.0000 (3)

Geometric parameters (Å, º)

C1—N1	1.454 (2)	N2—O2	1.2264 (15)
C1—N3	1.4652 (15)	N3—N4	1.4239 (14)
C1—C4	1.591 (2)	N4—O4	1.2154 (15)
C2—N7	1.451 (2)	N4—O3	1.2164 (14)
C2—N1	1.469 (2)	N5—N6	1.3968 (14)
C2—C3	1.577 (2)	N6—O6	1.2126 (14)
C3—N5	1.4318 (15)	N6—O5	1.2208 (14)
C3—N3	1.480 (2)	N7—N8	1.4210 (15)
C4—N9	1.457 (2)	N8—O7	1.2151 (14)
C4—N11	1.4638 (15)	N8—O8	1.2170 (15)
C5—N7	1.447 (2)	N9—N10	1.4434 (13)
C5—N9	1.491 (2)	N10—O9	1.2101 (15)
C5—C6	1.573 (2)	N10—O10	1.2217 (15)
C6—N5	1.4407 (14)	N11—N12	1.3732 (15)
C6—N11	1.470 (2)	N12—O12	1.2236 (14)
N1—N2	1.4024 (14)	N12—O11	1.2251 (15)
N2—O1	1.2153 (15)
N1—C1—N3	104.23 (9)	O4—N4—O3	127.40 (11)
N1—C1—C4	109.37 (10)	O4—N4—N3	117.22 (10)
N3—C1—C4	107.39 (9)	O3—N4—N3	115.22 (10)
N7—C2—N1	110.69 (9)	N6—N5—C3	120.43 (9)
N7—C2—C3	108.59 (9)	N6—N5—C6	119.73 (9)
N1—C2—C3	104.32 (10)	C3—N5—C6	117.73 (9)
N5—C3—N3	109.89 (10)	O6—N6—O5	127.34 (11)
N5—C3—C2	108.99 (10)	O6—N6—N5	116.57 (10)
N3—C3—C2	104.21 (9)	O5—N6—N5	116.02 (10)
N9—C4—N11	99.50 (9)	N8—N7—C5	115.47 (9)
N9—C4—C1	110.49 (10)	N8—N7—C2	113.92 (9)
N11—C4—C1	113.22 (9)	C5—N7—C2	116.42 (10)
N7—C5—N9	111.26 (9)	O7—N8—O8	127.13 (12)
N7—C5—C6	108.30 (9)	O7—N8—N7	115.69 (10)
N9—C5—C6	105.66 (10)	O8—N8—N7	117.12 (10)
N5—C6—N11	112.98 (10)	N10—N9—C4	113.10 (9)
N5—C6—C5	109.33 (9)	N10—N9—C5	111.62 (9)
N11—C6—C5	99.90 (9)	C4—N9—C5	106.82 (9)
N2—N1—C1	118.15 (10)	O9—N10—O10	126.99 (10)
N2—N1—C2	119.00 (10)	O9—N10—N9	115.81 (10)
C1—N1—C2	108.12 (9)	O10—N10—N9	117.12 (10)
O1—N2—O2	126.36 (11)	N12—N11—C4	119.68 (10)
O1—N2—N1	117.77 (10)	N12—N11—C6	120.07 (10)
O2—N2—N1	115.79 (11)	C4—N11—C6	110.59 (9)
N4—N3—C1	117.25 (10)	O12—N12—O11	126.56 (11)
N4—N3—C3	116.00 (9)	O12—N12—N11	116.47 (11)
C1—N3—C3	107.64 (10)	O11—N12—N11	116.95 (10)

(298eHNIW)

Crystal data

C6H6N12O12	F(000) = 888
Mr = 438.23	Dx = 2.035 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.8628 (11) Å	Cell parameters from 2430 reflections
b = 12.5928 (16) Å	θ = 4.5–51.2°
c = 13.3947 (17) Å	µ = 0.20 mm^−1
β = 106.920 (2)°	T = 298 K
V = 1430.2 (3) Å^3	Block, colorless
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection

Radiation source: fine-focus sealed tube	2174 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
Absorption correction: empirical Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany	θmax = 29.7°, θmin = 2.3°
Tmin = 0.858, Tmax = 1.000	h = −12→11
9342 measured reflections	k = −16→17
3735 independent reflections	l = −18→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.0526P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.058
3735 reflections	Δρmax = 0.26 e Å^−3
296 parameters	Δρmin = −0.25 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0094 (13)

Special details

Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS. No formal measure of the extent of decay is printed out by this program. The final unit cell is obtained from the refinement of the XYZ weighted centroids of reflections above 15 σ(I).

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.4311 (3)	−0.23426 (18)	0.21368 (18)	0.0226 (5)
H1	0.389 (3)	−0.297 (2)	0.1834 (18)	0.029 (7)*
C3	0.6578 (3)	−0.11856 (18)	0.22188 (17)	0.0235 (5)
H3	0.746 (3)	−0.1124 (17)	0.1963 (17)	0.024 (6)*
C5	0.5852 (3)	−0.06188 (18)	0.37374 (18)	0.0229 (5)
H5	0.628 (3)	−0.0344 (17)	0.4418 (18)	0.023 (6)*
C7	0.5456 (3)	−0.01946 (18)	0.19291 (17)	0.0231 (5)
H7	0.582 (3)	0.0302 (17)	0.1539 (16)	0.021 (6)*
C9	0.3175 (3)	−0.13616 (18)	0.18368 (18)	0.0235 (5)
H9	0.221 (3)	−0.1552 (18)	0.1344 (17)	0.024 (6)*
C11	0.4378 (3)	−0.13681 (17)	0.36616 (18)	0.0220 (5)
H11	0.420 (3)	−0.1383 (18)	0.4300 (18)	0.030 (7)*
N1	0.6462 (3)	−0.29780 (17)	0.14733 (16)	0.0334 (5)
N2	0.5678 (2)	−0.21221 (14)	0.17942 (14)	0.0242 (5)
N3	0.7865 (2)	−0.19742 (16)	0.39606 (16)	0.0301 (5)
N4	0.7066 (2)	−0.11325 (14)	0.33720 (14)	0.0238 (4)
N5	0.4523 (2)	0.10326 (15)	0.30473 (16)	0.0265 (5)
N6	0.5518 (2)	0.02215 (14)	0.29654 (13)	0.0221 (4)
N7	0.3128 (3)	−0.01271 (17)	0.03894 (15)	0.0308 (5)
N8	0.3894 (2)	−0.05447 (15)	0.13678 (14)	0.0260 (5)
N9	0.1521 (3)	−0.10523 (16)	0.30145 (18)	0.0322 (5)
N10	0.3028 (2)	−0.09681 (15)	0.28366 (14)	0.0233 (4)
N11	0.4182 (2)	−0.33030 (15)	0.37243 (17)	0.0299 (5)
N12	0.4725 (2)	−0.24022 (13)	0.32829 (14)	0.0222 (4)
O1	0.5890 (3)	−0.38519 (15)	0.14840 (18)	0.0583 (6)
O2	0.7598 (2)	−0.27482 (15)	0.11910 (14)	0.0425 (5)
O3	0.8488 (2)	−0.26021 (14)	0.35129 (15)	0.0425 (5)
O4	0.7889 (2)	−0.19887 (15)	0.48707 (14)	0.0452 (5)
O5	0.4238 (2)	0.11200 (13)	0.38849 (13)	0.0364 (4)
O6	0.4058 (2)	0.16054 (12)	0.22897 (13)	0.0333 (4)
O7	0.1913 (3)	−0.05533 (17)	−0.00819 (14)	0.0549 (6)
O8	0.3753 (2)	0.06240 (14)	0.00985 (13)	0.0380 (5)
O9	0.0395 (2)	−0.11530 (14)	0.22564 (15)	0.0407 (5)
O10	0.1525 (2)	−0.09586 (16)	0.39190 (16)	0.0529 (6)
O11	0.4019 (2)	−0.31862 (14)	0.45821 (15)	0.0457 (5)
O12	0.4020 (2)	−0.41139 (13)	0.32126 (14)	0.0389 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0235 (13)	0.0202 (12)	0.0234 (13)	−0.0010 (10)	0.0058 (10)	−0.0026 (10)
C3	0.0213 (13)	0.0297 (13)	0.0199 (12)	0.0009 (11)	0.0067 (10)	0.0016 (10)
C5	0.0251 (13)	0.0238 (12)	0.0173 (12)	−0.0005 (10)	0.0025 (10)	−0.0012 (10)
C7	0.0226 (13)	0.0269 (12)	0.0204 (12)	−0.0018 (11)	0.0073 (10)	0.0026 (10)
C9	0.0202 (13)	0.0250 (12)	0.0226 (12)	−0.0009 (10)	0.0020 (10)	−0.0012 (10)
C11	0.0247 (14)	0.0213 (11)	0.0194 (12)	0.0009 (10)	0.0056 (10)	−0.0006 (9)
N1	0.0348 (13)	0.0339 (13)	0.0313 (12)	0.0101 (11)	0.0093 (10)	−0.0023 (9)
N2	0.0239 (12)	0.0253 (10)	0.0238 (11)	0.0011 (9)	0.0075 (9)	−0.0066 (8)
N3	0.0245 (12)	0.0336 (12)	0.0282 (12)	0.0043 (10)	0.0016 (9)	0.0034 (9)
N4	0.0200 (10)	0.0276 (10)	0.0216 (10)	0.0027 (9)	0.0024 (8)	0.0017 (8)
N5	0.0227 (11)	0.0238 (10)	0.0323 (12)	−0.0051 (9)	0.0069 (9)	−0.0028 (9)
N6	0.0244 (11)	0.0202 (10)	0.0214 (10)	0.0004 (9)	0.0060 (8)	−0.0004 (8)
N7	0.0341 (13)	0.0345 (12)	0.0215 (11)	0.0109 (11)	0.0044 (10)	−0.0002 (9)
N8	0.0233 (12)	0.0313 (11)	0.0191 (10)	0.0005 (9)	−0.0005 (8)	0.0064 (8)
N9	0.0277 (13)	0.0268 (11)	0.0461 (14)	0.0025 (10)	0.0169 (11)	0.0069 (10)
N10	0.0183 (11)	0.0270 (10)	0.0261 (11)	0.0001 (8)	0.0086 (8)	−0.0006 (8)
N11	0.0255 (12)	0.0238 (11)	0.0394 (13)	0.0002 (9)	0.0079 (10)	0.0065 (10)
N12	0.0267 (11)	0.0183 (9)	0.0216 (10)	−0.0008 (8)	0.0071 (8)	−0.0002 (7)
O1	0.0538 (15)	0.0287 (11)	0.0991 (18)	0.0040 (10)	0.0331 (13)	−0.0134 (11)
O2	0.0406 (12)	0.0514 (12)	0.0433 (11)	0.0144 (10)	0.0244 (10)	0.0020 (9)
O3	0.0395 (12)	0.0467 (11)	0.0433 (11)	0.0198 (10)	0.0153 (9)	0.0084 (9)
O4	0.0521 (13)	0.0574 (12)	0.0206 (10)	0.0130 (10)	0.0021 (8)	0.0093 (9)
O5	0.0429 (12)	0.0379 (10)	0.0316 (10)	0.0030 (9)	0.0161 (8)	−0.0081 (8)
O6	0.0345 (11)	0.0251 (9)	0.0392 (10)	0.0037 (8)	0.0089 (8)	0.0079 (8)
O7	0.0479 (13)	0.0612 (14)	0.0373 (11)	−0.0059 (11)	−0.0165 (10)	0.0009 (10)
O8	0.0431 (12)	0.0428 (11)	0.0310 (10)	0.0096 (9)	0.0153 (9)	0.0150 (8)
O9	0.0201 (10)	0.0395 (10)	0.0595 (13)	−0.0018 (9)	0.0068 (9)	0.0067 (9)
O10	0.0460 (13)	0.0737 (15)	0.0507 (13)	0.0092 (11)	0.0324 (10)	0.0042 (11)
O11	0.0643 (15)	0.0405 (11)	0.0418 (12)	−0.0018 (10)	0.0306 (10)	0.0095 (9)
O12	0.0412 (12)	0.0206 (9)	0.0520 (12)	−0.0046 (8)	0.0092 (9)	−0.0026 (8)

Geometric parameters (Å, º)

C1—N2	1.442 (3)	C11—H11	0.91 (2)
C1—N12	1.473 (3)	N1—O2	1.210 (3)
C1—C9	1.571 (3)	N1—O1	1.213 (3)
C1—H1	0.92 (2)	N1—N2	1.415 (3)
C3—N2	1.445 (3)	N3—O4	1.213 (2)
C3—N4	1.480 (3)	N3—O3	1.218 (3)
C3—C7	1.573 (3)	N3—N4	1.386 (3)
C3—H3	0.94 (2)	N5—O6	1.215 (2)
C5—N6	1.449 (3)	N5—O5	1.225 (2)
C5—N4	1.457 (3)	N5—N6	1.374 (3)
C5—C11	1.590 (3)	N7—O7	1.204 (3)
C5—H5	0.95 (2)	N7—O8	1.216 (3)
C7—N8	1.439 (3)	N7—N8	1.392 (3)
C7—N6	1.470 (3)	N9—O9	1.205 (3)
C7—H7	0.93 (2)	N9—O10	1.216 (3)
C9—N8	1.446 (3)	N9—N10	1.427 (3)
C9—N10	1.469 (3)	N11—O11	1.208 (3)
C9—H9	0.95 (2)	N11—O12	1.215 (2)
C11—N10	1.462 (3)	N11—N12	1.426 (3)
C11—N12	1.462 (3)
N2—C1—N12	111.38 (19)	O2—N1—O1	127.5 (2)
N2—C1—C9	107.63 (18)	O2—N1—N2	116.1 (2)
N12—C1—C9	104.66 (17)	O1—N1—N2	116.4 (2)
N2—C1—H1	107.1 (15)	N1—N2—C1	118.82 (19)
N12—C1—H1	111.2 (14)	N1—N2—C3	118.54 (19)
C9—C1—H1	114.9 (15)	C1—N2—C3	116.80 (18)
N2—C3—N4	114.07 (18)	O4—N3—O3	127.4 (2)
N2—C3—C7	108.27 (18)	O4—N3—N4	116.1 (2)
N4—C3—C7	101.14 (17)	O3—N3—N4	116.51 (19)
N2—C3—H3	110.2 (13)	N3—N4—C5	116.98 (17)
N4—C3—H3	110.9 (14)	N3—N4—C3	120.32 (17)
C7—C3—H3	112.1 (13)	C5—N4—C3	110.55 (18)
N6—C5—N4	95.85 (16)	O6—N5—O5	127.0 (2)
N6—C5—C11	113.24 (19)	O6—N5—N6	116.36 (19)
N4—C5—C11	112.85 (18)	O5—N5—N6	116.62 (19)
N6—C5—H5	111.3 (13)	N5—N6—C5	119.24 (18)
N4—C5—H5	110.9 (14)	N5—N6—C7	119.45 (18)
C11—C5—H5	111.8 (14)	C5—N6—C7	110.95 (17)
N8—C7—N6	111.65 (19)	O7—N7—O8	126.9 (2)
N8—C7—C3	109.22 (18)	O7—N7—N8	116.2 (2)
N6—C7—C3	101.70 (17)	O8—N7—N8	116.9 (2)
N8—C7—H7	110.4 (14)	N7—N8—C7	120.53 (19)
N6—C7—H7	111.5 (13)	N7—N8—C9	121.45 (19)
C3—C7—H7	112.1 (14)	C7—N8—C9	118.00 (18)
N8—C9—N10	108.86 (18)	O9—N9—O10	127.7 (2)
N8—C9—C1	109.86 (19)	O9—N9—N10	116.9 (2)
N10—C9—C1	104.62 (17)	O10—N9—N10	115.3 (2)
N8—C9—H9	107.4 (14)	N9—N10—C11	116.61 (18)
N10—C9—H9	114.9 (14)	N9—N10—C9	117.57 (19)
C1—C9—H9	111.1 (14)	C11—N10—C9	107.63 (17)
N10—C11—N12	104.66 (18)	O11—N11—O12	127.7 (2)
N10—C11—C5	108.67 (18)	O11—N11—N12	116.46 (19)
N12—C11—C5	107.39 (18)	O12—N11—N12	115.7 (2)
N10—C11—H11	112.8 (15)	N11—N12—C11	115.75 (18)
N12—C11—H11	114.7 (15)	N11—N12—C1	117.46 (18)
C5—C11—H11	108.3 (15)	C11—N12—C1	107.61 (17)

(250eHNIW)

Crystal data

C6H6N12O12	F(000) = 888
Mr = 438.23	Dx = 2.050 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.8408 (9) Å	Cell parameters from 2341 reflections
b = 12.5622 (12) Å	θ = 4.6–51.3°
c = 13.3577 (13) Å	µ = 0.20 mm^−1
β = 106.820 (2)°	T = 250 K
V = 1420.0 (2) Å^3	Block, colorless
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection

Radiation source: fine-focus sealed tube	2338 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
Absorption correction: empirical Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany	θmax = 29.7°, θmin = 2.3°
Tmin = 0.872, Tmax = 1.000	h = −10→12
9290 measured reflections	k = −16→17
3712 independent reflections	l = −15→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2) + (0.0526P)^2 + 0.0546P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.038
3712 reflections	Δρmax = 0.35 e Å^−3
296 parameters	Δρmin = −0.27 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0080 (13)

Special details

Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS. No formal measure of the extent of decay is printed out by this program. The final unit cell is obtained from the refinement of the XYZ weighted centroids of reflections above 15 σ(I).

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.4318 (3)	−0.23479 (17)	0.21376 (16)	0.0195 (5)
H1	0.387 (3)	−0.2951 (18)	0.1852 (16)	0.016 (6)*
C3	0.6590 (3)	−0.11850 (17)	0.22197 (16)	0.0200 (5)
H3	0.747 (3)	−0.1165 (16)	0.1952 (17)	0.024 (6)*
C5	0.5857 (3)	−0.06175 (17)	0.37419 (17)	0.0198 (5)
H5	0.628 (3)	−0.0340 (17)	0.4418 (18)	0.022 (6)*
C7	0.5462 (3)	−0.01940 (17)	0.19285 (16)	0.0199 (5)
H7	0.579 (2)	0.0313 (15)	0.1532 (15)	0.009 (5)*
C9	0.3173 (3)	−0.13629 (17)	0.18320 (17)	0.0202 (5)
H9	0.219 (3)	−0.1546 (16)	0.1381 (16)	0.015 (5)*
C11	0.4380 (3)	−0.13684 (16)	0.36628 (17)	0.0192 (5)
H11	0.414 (2)	−0.1421 (16)	0.4273 (16)	0.015 (5)*
N1	0.6466 (2)	−0.29818 (15)	0.14683 (15)	0.0280 (5)
N2	0.5682 (2)	−0.21250 (14)	0.17918 (13)	0.0212 (4)
N3	0.7865 (2)	−0.19793 (15)	0.39555 (14)	0.0255 (4)
N4	0.7066 (2)	−0.11341 (13)	0.33711 (13)	0.0195 (4)
N5	0.4517 (2)	0.10351 (13)	0.30484 (15)	0.0224 (4)
N6	0.5518 (2)	0.02239 (13)	0.29651 (13)	0.0188 (4)
N7	0.3134 (2)	−0.01223 (15)	0.03873 (14)	0.0263 (4)
N8	0.3895 (2)	−0.05428 (14)	0.13648 (13)	0.0220 (4)
N9	0.1512 (2)	−0.10572 (15)	0.30174 (16)	0.0271 (5)
N10	0.3028 (2)	−0.09683 (14)	0.28387 (13)	0.0207 (4)
N11	0.4181 (2)	−0.33109 (14)	0.37247 (15)	0.0247 (4)
N12	0.4726 (2)	−0.24073 (12)	0.32868 (13)	0.0190 (4)
O1	0.5896 (2)	−0.38588 (13)	0.14767 (16)	0.0477 (5)
O2	0.7608 (2)	−0.27506 (14)	0.11842 (13)	0.0354 (4)
O3	0.8486 (2)	−0.26118 (13)	0.35111 (13)	0.0353 (4)
O4	0.7893 (2)	−0.19960 (14)	0.48719 (12)	0.0372 (4)
O5	0.4228 (2)	0.11217 (12)	0.38878 (12)	0.0302 (4)
O6	0.4048 (2)	0.16068 (12)	0.22868 (12)	0.0288 (4)
O7	0.1910 (2)	−0.05510 (15)	−0.00904 (13)	0.0455 (5)
O8	0.3756 (2)	0.06320 (13)	0.00969 (12)	0.0329 (4)
O9	0.0387 (2)	−0.11577 (13)	0.22548 (14)	0.0354 (4)
O10	0.1516 (2)	−0.09596 (15)	0.39247 (14)	0.0453 (5)
O11	0.4016 (2)	−0.31922 (13)	0.45840 (13)	0.0378 (5)
O12	0.4018 (2)	−0.41231 (12)	0.32130 (13)	0.0334 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0193 (11)	0.0192 (11)	0.0194 (11)	−0.0013 (9)	0.0048 (9)	−0.0026 (9)
C3	0.0187 (11)	0.0230 (11)	0.0193 (11)	0.0013 (9)	0.0072 (9)	0.0012 (9)
C5	0.0217 (12)	0.0213 (11)	0.0156 (11)	−0.0018 (9)	0.0042 (9)	−0.0023 (9)
C7	0.0191 (12)	0.0225 (11)	0.0177 (11)	−0.0027 (9)	0.0046 (9)	0.0013 (9)
C9	0.0138 (11)	0.0235 (11)	0.0219 (11)	−0.0003 (9)	0.0029 (9)	−0.0013 (9)
C11	0.0226 (12)	0.0204 (11)	0.0158 (11)	0.0003 (9)	0.0074 (9)	0.0007 (8)
N1	0.0276 (11)	0.0293 (11)	0.0277 (11)	0.0094 (9)	0.0088 (9)	−0.0020 (8)
N2	0.0207 (10)	0.0234 (9)	0.0203 (10)	0.0020 (8)	0.0073 (8)	−0.0040 (7)
N3	0.0218 (10)	0.0298 (11)	0.0233 (11)	0.0033 (9)	0.0040 (8)	0.0025 (8)
N4	0.0171 (9)	0.0210 (9)	0.0190 (9)	0.0019 (8)	0.0030 (7)	0.0023 (7)
N5	0.0209 (10)	0.0177 (9)	0.0277 (11)	−0.0036 (8)	0.0059 (8)	−0.0033 (8)
N6	0.0197 (10)	0.0182 (9)	0.0186 (9)	0.0000 (8)	0.0056 (7)	0.0005 (7)
N7	0.0267 (11)	0.0300 (11)	0.0203 (10)	0.0102 (9)	0.0041 (9)	0.0001 (8)
N8	0.0211 (10)	0.0257 (10)	0.0167 (9)	−0.0001 (8)	0.0016 (8)	0.0053 (8)
N9	0.0228 (11)	0.0219 (10)	0.0407 (13)	0.0030 (8)	0.0155 (10)	0.0041 (8)
N10	0.0172 (9)	0.0236 (9)	0.0223 (10)	0.0008 (8)	0.0071 (8)	0.0005 (7)
N11	0.0215 (10)	0.0222 (10)	0.0298 (11)	−0.0002 (8)	0.0068 (8)	0.0049 (8)
N12	0.0215 (10)	0.0151 (8)	0.0214 (10)	−0.0006 (8)	0.0076 (8)	0.0011 (7)
O1	0.0453 (12)	0.0235 (10)	0.0800 (15)	0.0008 (9)	0.0274 (11)	−0.0108 (9)
O2	0.0333 (10)	0.0417 (10)	0.0373 (10)	0.0109 (9)	0.0199 (8)	0.0024 (8)
O3	0.0336 (10)	0.0376 (10)	0.0362 (10)	0.0152 (8)	0.0127 (8)	0.0064 (8)
O4	0.0445 (11)	0.0449 (10)	0.0189 (9)	0.0112 (9)	0.0039 (7)	0.0072 (8)
O5	0.0351 (10)	0.0336 (9)	0.0254 (9)	0.0016 (8)	0.0142 (7)	−0.0066 (7)
O6	0.0288 (10)	0.0230 (8)	0.0337 (9)	0.0019 (7)	0.0076 (7)	0.0076 (7)
O7	0.0394 (11)	0.0490 (12)	0.0332 (10)	−0.0038 (10)	−0.0130 (9)	0.0021 (9)
O8	0.0392 (11)	0.0359 (10)	0.0259 (9)	0.0073 (8)	0.0132 (8)	0.0127 (7)
O9	0.0187 (9)	0.0339 (9)	0.0514 (11)	−0.0021 (8)	0.0066 (8)	0.0061 (8)
O10	0.0413 (12)	0.0621 (13)	0.0423 (11)	0.0074 (10)	0.0274 (9)	0.0030 (9)
O11	0.0517 (12)	0.0337 (10)	0.0352 (10)	−0.0019 (9)	0.0241 (9)	0.0065 (8)
O12	0.0364 (10)	0.0191 (8)	0.0415 (10)	−0.0024 (7)	0.0065 (8)	−0.0008 (7)

Geometric parameters (Å, º)

C1—N2	1.438 (3)	C11—H11	0.90 (2)
C1—N12	1.474 (3)	N1—O2	1.212 (3)
C1—C9	1.576 (3)	N1—O1	1.213 (2)
C1—H1	0.89 (2)	N1—N2	1.414 (2)
C3—N2	1.449 (3)	N3—O3	1.214 (2)
C3—N4	1.474 (3)	N3—O4	1.217 (2)
C3—C7	1.572 (3)	N3—N4	1.385 (2)
C3—H3	0.94 (2)	N5—O6	1.216 (2)
C5—N6	1.450 (3)	N5—O5	1.225 (2)
C5—N4	1.454 (3)	N5—N6	1.375 (2)
C5—C11	1.589 (3)	N7—O7	1.212 (3)
C5—H5	0.94 (2)	N7—O8	1.214 (2)
C7—N8	1.441 (3)	N7—N8	1.389 (2)
C7—N6	1.468 (3)	N9—O9	1.207 (3)
C7—H7	0.93 (2)	N9—O10	1.217 (2)
C9—N8	1.445 (3)	N9—N10	1.433 (3)
C9—N10	1.473 (3)	N11—O11	1.208 (2)
C9—H9	0.93 (2)	N11—O12	1.213 (2)
C11—N10	1.460 (3)	N11—N12	1.423 (2)
C11—N12	1.462 (3)
N2—C1—N12	111.69 (18)	O2—N1—O1	127.3 (2)
N2—C1—C9	107.42 (17)	O2—N1—N2	116.09 (19)
N12—C1—C9	104.75 (16)	O1—N1—N2	116.54 (19)
N2—C1—H1	110.1 (14)	N1—N2—C1	118.74 (17)
N12—C1—H1	110.4 (13)	N1—N2—C3	118.46 (17)
C9—C1—H1	112.4 (14)	C1—N2—C3	116.87 (16)
N2—C3—N4	113.92 (17)	O3—N3—O4	126.88 (19)
N2—C3—C7	107.99 (17)	O3—N3—N4	117.10 (18)
N4—C3—C7	101.13 (16)	O4—N3—N4	116.00 (18)
N2—C3—H3	107.1 (13)	N3—N4—C5	117.12 (16)
N4—C3—H3	112.1 (14)	N3—N4—C3	120.01 (16)
C7—C3—H3	114.6 (13)	C5—N4—C3	111.02 (16)
N6—C5—N4	95.84 (15)	O6—N5—O5	127.05 (19)
N6—C5—C11	112.90 (18)	O6—N5—N6	116.22 (17)
N4—C5—C11	112.53 (17)	O5—N5—N6	116.70 (17)
N6—C5—H5	111.1 (13)	N5—N6—C5	119.14 (16)
N4—C5—H5	111.3 (14)	N5—N6—C7	119.64 (17)
C11—C5—H5	112.2 (13)	C5—N6—C7	110.96 (16)
N8—C7—N6	111.48 (17)	O7—N7—O8	126.6 (2)
N8—C7—C3	109.49 (17)	O7—N7—N8	116.22 (19)
N6—C7—C3	101.77 (16)	O8—N7—N8	117.15 (19)
N8—C7—H7	108.7 (13)	N7—N8—C7	120.44 (17)
N6—C7—H7	111.3 (12)	N7—N8—C9	121.55 (18)
C3—C7—H7	114.1 (12)	C7—N8—C9	117.98 (17)
N8—C9—N10	108.67 (17)	O9—N9—O10	128.0 (2)
N8—C9—C1	109.94 (17)	O9—N9—N10	116.74 (18)
N10—C9—C1	104.29 (16)	O10—N9—N10	115.10 (19)
N8—C9—H9	110.0 (13)	N9—N10—C11	116.68 (16)
N10—C9—H9	111.3 (13)	N9—N10—C9	117.31 (17)
C1—C9—H9	112.5 (13)	C11—N10—C9	107.69 (16)
N10—C11—N12	104.79 (17)	O11—N11—O12	127.73 (19)
N10—C11—C5	108.86 (17)	O11—N11—N12	116.14 (17)
N12—C11—C5	107.65 (17)	O12—N11—N12	116.01 (18)
N10—C11—H11	110.7 (14)	N11—N12—C11	116.20 (17)
N12—C11—H11	111.8 (13)	N11—N12—C1	117.31 (17)
C5—C11—H11	112.6 (14)	C11—N12—C1	107.47 (16)

(200eHNIW)

Crystal data

C6H6N12O12	F(000) = 888
Mr = 438.23	Dx = 2.061 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.8212 (10) Å	Cell parameters from 2367 reflections
b = 12.5368 (14) Å	θ = 4.6–51.4°
c = 13.3330 (15) Å	µ = 0.20 mm^−1
β = 106.740 (2)°	T = 200 K
V = 1412.0 (3) Å^3	Block, colorless
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection

Radiation source: fine-focus sealed tube	2355 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Absorption correction: empirical Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany	θmax = 29.8°, θmin = 2.3°
Tmin = 0.878, Tmax = 1.000	h = −10→12
9186 measured reflections	k = −16→17
3681 independent reflections	l = −15→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.053P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max = 0.039
3681 reflections	Δρmax = 0.33 e Å^−3
296 parameters	Δρmin = −0.32 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0084 (12)

Special details

Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS. No formal measure of the extent of decay is printed out by this program. The final unit cell is obtained from the refinement of the XYZ weighted centroids of reflections above 15 σ(I).

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.4318 (2)	−0.23488 (16)	0.21342 (15)	0.0159 (4)
H1	0.385 (2)	−0.2953 (17)	0.1843 (16)	0.018 (5)*
C3	0.6595 (2)	−0.11861 (15)	0.22155 (15)	0.0169 (4)
H3	0.752 (3)	−0.1157 (14)	0.1953 (15)	0.016 (5)*
C5	0.5861 (2)	−0.06165 (15)	0.37452 (15)	0.0163 (4)
H5	0.627 (3)	−0.0362 (16)	0.4427 (17)	0.018 (5)*
C7	0.5464 (2)	−0.01934 (15)	0.19260 (15)	0.0161 (4)
H7	0.581 (2)	0.0306 (16)	0.1512 (15)	0.018 (5)*
C9	0.3170 (2)	−0.13641 (16)	0.18327 (15)	0.0173 (4)
H9	0.218 (3)	−0.1539 (15)	0.1347 (15)	0.016 (5)*
C11	0.4379 (2)	−0.13712 (15)	0.36653 (15)	0.0158 (4)
H11	0.419 (2)	−0.1406 (15)	0.4273 (15)	0.012 (5)*
N1	0.6470 (2)	−0.29860 (14)	0.14643 (13)	0.0229 (4)
N2	0.56852 (19)	−0.21268 (12)	0.17872 (12)	0.0175 (4)
N3	0.7870 (2)	−0.19838 (13)	0.39572 (13)	0.0212 (4)
N4	0.70748 (19)	−0.11347 (12)	0.33729 (12)	0.0169 (4)
N5	0.4512 (2)	0.10388 (12)	0.30481 (13)	0.0189 (4)
N6	0.55232 (19)	0.02268 (12)	0.29673 (12)	0.0154 (3)
N7	0.3129 (2)	−0.01225 (14)	0.03851 (12)	0.0216 (4)
N8	0.38965 (19)	−0.05413 (13)	0.13632 (12)	0.0185 (4)
N9	0.1509 (2)	−0.10619 (13)	0.30209 (14)	0.0224 (4)
N10	0.30230 (19)	−0.09672 (13)	0.28369 (12)	0.0171 (4)
N11	0.4183 (2)	−0.33170 (13)	0.37268 (14)	0.0209 (4)
N12	0.4729 (2)	−0.24091 (12)	0.32864 (12)	0.0161 (4)
O1	0.5897 (2)	−0.38654 (12)	0.14692 (14)	0.0393 (4)
O2	0.76165 (19)	−0.27533 (12)	0.11781 (12)	0.0285 (4)
O3	0.84835 (18)	−0.26200 (12)	0.35037 (12)	0.0287 (4)
O4	0.78985 (19)	−0.20028 (12)	0.48761 (11)	0.0303 (4)
O5	0.42199 (18)	0.11248 (11)	0.38889 (11)	0.0249 (3)
O6	0.40408 (17)	0.16102 (11)	0.22832 (11)	0.0236 (3)
O7	0.1908 (2)	−0.05507 (13)	−0.00986 (12)	0.0375 (4)
O8	0.37611 (18)	0.06385 (11)	0.00934 (11)	0.0261 (4)
O9	0.03782 (17)	−0.11619 (11)	0.22545 (12)	0.0286 (4)
O10	0.1514 (2)	−0.09648 (13)	0.39299 (13)	0.0368 (4)
O11	0.4016 (2)	−0.32000 (11)	0.45896 (12)	0.0311 (4)
O12	0.40199 (18)	−0.41308 (11)	0.32130 (11)	0.0269 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0154 (10)	0.0156 (10)	0.0163 (10)	−0.0008 (8)	0.0038 (8)	−0.0012 (8)
C3	0.0163 (10)	0.0194 (10)	0.0155 (10)	−0.0013 (8)	0.0053 (8)	0.0006 (8)
C5	0.0175 (10)	0.0180 (10)	0.0127 (10)	0.0003 (8)	0.0031 (8)	−0.0005 (8)
C7	0.0148 (10)	0.0192 (10)	0.0145 (10)	−0.0015 (8)	0.0045 (8)	0.0012 (8)
C9	0.0148 (10)	0.0186 (10)	0.0172 (10)	−0.0010 (8)	0.0027 (8)	−0.0003 (8)
C11	0.0158 (10)	0.0190 (10)	0.0128 (10)	0.0015 (8)	0.0042 (8)	0.0004 (8)
N1	0.0225 (10)	0.0233 (10)	0.0231 (10)	0.0069 (8)	0.0070 (8)	−0.0023 (7)
N2	0.0171 (9)	0.0177 (8)	0.0190 (9)	0.0003 (7)	0.0071 (7)	−0.0042 (7)
N3	0.0171 (9)	0.0249 (9)	0.0196 (9)	0.0020 (8)	0.0021 (7)	0.0015 (7)
N4	0.0148 (8)	0.0191 (8)	0.0156 (8)	0.0022 (7)	0.0025 (7)	0.0013 (7)
N5	0.0166 (9)	0.0165 (8)	0.0233 (9)	−0.0031 (7)	0.0051 (7)	−0.0025 (7)
N6	0.0173 (9)	0.0132 (8)	0.0159 (8)	0.0005 (7)	0.0051 (7)	−0.0004 (6)
N7	0.0230 (10)	0.0254 (9)	0.0150 (9)	0.0076 (8)	0.0034 (7)	0.0003 (7)
N8	0.0162 (9)	0.0226 (9)	0.0147 (8)	−0.0013 (7)	0.0012 (7)	0.0033 (7)
N9	0.0211 (10)	0.0174 (9)	0.0321 (11)	0.0019 (7)	0.0132 (8)	0.0037 (7)
N10	0.0137 (8)	0.0200 (8)	0.0185 (9)	0.0014 (7)	0.0061 (7)	0.0005 (7)
N11	0.0173 (9)	0.0183 (9)	0.0269 (10)	−0.0001 (7)	0.0061 (8)	0.0045 (7)
N12	0.0184 (9)	0.0134 (8)	0.0171 (8)	−0.0014 (7)	0.0064 (7)	0.0003 (6)
O1	0.0381 (10)	0.0197 (8)	0.0654 (12)	0.0008 (8)	0.0234 (9)	−0.0088 (8)
O2	0.0267 (9)	0.0344 (9)	0.0293 (8)	0.0074 (7)	0.0159 (7)	0.0022 (7)
O3	0.0254 (8)	0.0317 (8)	0.0307 (9)	0.0122 (7)	0.0109 (7)	0.0049 (7)
O4	0.0357 (10)	0.0374 (9)	0.0151 (8)	0.0073 (8)	0.0031 (6)	0.0063 (7)
O5	0.0285 (9)	0.0279 (8)	0.0214 (8)	0.0005 (7)	0.0120 (6)	−0.0066 (6)
O6	0.0216 (8)	0.0201 (7)	0.0286 (8)	0.0020 (6)	0.0065 (6)	0.0064 (6)
O7	0.0333 (10)	0.0415 (10)	0.0263 (9)	−0.0036 (8)	−0.0093 (7)	−0.0003 (7)
O8	0.0294 (9)	0.0294 (8)	0.0215 (8)	0.0057 (7)	0.0106 (7)	0.0095 (6)
O9	0.0149 (8)	0.0271 (8)	0.0419 (9)	−0.0017 (7)	0.0053 (7)	0.0065 (7)
O10	0.0320 (10)	0.0520 (11)	0.0339 (10)	0.0082 (8)	0.0215 (8)	0.0036 (8)
O11	0.0424 (11)	0.0284 (8)	0.0284 (9)	−0.0017 (7)	0.0196 (8)	0.0056 (7)
O12	0.0281 (9)	0.0160 (7)	0.0342 (9)	−0.0029 (6)	0.0053 (7)	−0.0022 (6)

Geometric parameters (Å, º)

C1—N2	1.438 (2)	C11—H11	0.876 (19)
C1—N12	1.475 (2)	N1—O1	1.214 (2)
C1—C9	1.574 (3)	N1—O2	1.215 (2)
C1—H1	0.90 (2)	N1—N2	1.413 (2)
C3—N2	1.448 (2)	N3—O3	1.218 (2)
C3—N4	1.479 (2)	N3—O4	1.218 (2)
C3—C7	1.572 (3)	N3—N4	1.385 (2)
C3—H3	0.97 (2)	N5—O6	1.217 (2)
C5—N6	1.451 (2)	N5—O5	1.225 (2)
C5—N4	1.456 (2)	N5—N6	1.378 (2)
C5—C11	1.592 (3)	N7—O7	1.209 (2)
C5—H5	0.93 (2)	N7—O8	1.224 (2)
C7—N8	1.438 (2)	N7—N8	1.388 (2)
C7—N6	1.472 (2)	N9—O9	1.211 (2)
C7—H7	0.94 (2)	N9—O10	1.217 (2)
C9—N8	1.448 (2)	N9—N10	1.431 (2)
C9—N10	1.469 (2)	N11—O11	1.210 (2)
C9—H9	0.95 (2)	N11—O12	1.214 (2)
C11—N12	1.461 (2)	N11—N12	1.427 (2)
C11—N10	1.465 (2)
N2—C1—N12	111.57 (16)	O1—N1—O2	127.28 (17)
N2—C1—C9	107.67 (15)	O1—N1—N2	116.70 (17)
N12—C1—C9	104.67 (15)	O2—N1—N2	115.97 (16)
N2—C1—H1	110.3 (13)	N1—N2—C1	118.73 (15)
N12—C1—H1	110.6 (13)	N1—N2—C3	118.43 (16)
C9—C1—H1	111.8 (13)	C1—N2—C3	116.87 (15)
N2—C3—N4	113.97 (15)	O3—N3—O4	127.08 (17)
N2—C3—C7	107.90 (15)	O3—N3—N4	116.72 (16)
N4—C3—C7	101.07 (14)	O4—N3—N4	116.19 (16)
N2—C3—H3	108.3 (11)	N3—N4—C5	117.00 (15)
N4—C3—H3	110.8 (11)	N3—N4—C3	119.98 (14)
C7—C3—H3	114.8 (11)	C5—N4—C3	110.96 (15)
N6—C5—N4	95.80 (14)	O6—N5—O5	127.12 (17)
N6—C5—C11	112.93 (16)	O6—N5—N6	116.23 (16)
N4—C5—C11	112.47 (15)	O5—N5—N6	116.61 (16)
N6—C5—H5	112.9 (12)	N5—N6—C5	119.14 (15)
N4—C5—H5	111.5 (13)	N5—N6—C7	119.37 (15)
C11—C5—H5	110.5 (13)	C5—N6—C7	110.97 (14)
N8—C7—N6	111.59 (16)	O7—N7—O8	126.42 (17)
N8—C7—C3	109.57 (15)	O7—N7—N8	116.85 (17)
N6—C7—C3	101.79 (14)	O8—N7—N8	116.72 (17)
N8—C7—H7	108.8 (13)	N7—N8—C7	120.75 (16)
N6—C7—H7	112.7 (12)	N7—N8—C9	121.24 (16)
C3—C7—H7	112.3 (12)	C7—N8—C9	117.98 (15)
N8—C9—N10	108.61 (16)	O9—N9—O10	128.10 (19)
N8—C9—C1	109.69 (16)	O9—N9—N10	116.51 (16)
N10—C9—C1	104.61 (15)	O10—N9—N10	115.23 (17)
N8—C9—H9	107.6 (12)	N9—N10—C11	116.22 (15)
N10—C9—H9	113.3 (12)	N9—N10—C9	117.40 (15)
C1—C9—H9	112.9 (12)	C11—N10—C9	107.63 (15)
N12—C11—N10	104.78 (15)	O11—N11—O12	127.69 (17)
N12—C11—C5	107.53 (15)	O11—N11—N12	116.26 (16)
N10—C11—C5	108.74 (15)	O12—N11—N12	115.93 (16)
N12—C11—H11	113.1 (13)	N11—N12—C11	116.00 (15)
N10—C11—H11	112.4 (13)	N11—N12—C1	117.30 (15)
C5—C11—H11	110.1 (13)	C11—N12—C1	107.55 (15)

(150eHNIW)

Crystal data

C6H6N12O12	F(000) = 888
Mr = 438.23	Dx = 2.077 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.8004 (10) Å	Cell parameters from 2396 reflections
b = 12.4992 (14) Å	θ = 4.6–55.7°
c = 13.2985 (15) Å	µ = 0.20 mm^−1
β = 106.622 (2)°	T = 150 K
V = 1401.7 (3) Å^3	Block, colorless
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection

Radiation source: fine-focus sealed tube	2398 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
Absorption correction: empirical Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany	θmax = 29.6°, θmin = 2.3°
Tmin = 0.880, Tmax = 1.000	h = −10→12
9177 measured reflections	k = −16→17
3669 independent reflections	l = −15→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.100	w = 1/[σ^2(Fo^2) + (0.0493P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max = 0.036
3669 reflections	Δρmax = 0.35 e Å^−3
296 parameters	Δρmin = −0.32 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0085 (12)

Special details

Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS. No formal measure of the extent of decay is printed out by this program. The final unit cell is obtained from the refinement of the XYZ weighted centroids of reflections above 15 σ(I).

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.4317 (2)	−0.23561 (16)	0.21320 (15)	0.0133 (4)
H1	0.389 (2)	−0.2981 (17)	0.1851 (15)	0.014 (5)*
C3	0.6597 (2)	−0.11876 (15)	0.22120 (14)	0.0139 (4)
H3	0.750 (2)	−0.1159 (14)	0.1947 (15)	0.012 (5)*
C5	0.5863 (2)	−0.06174 (15)	0.37475 (15)	0.0145 (4)
H5	0.629 (3)	−0.0347 (17)	0.4449 (18)	0.021 (6)*
C7	0.5467 (2)	−0.01899 (15)	0.19250 (15)	0.0137 (4)
H7	0.580 (2)	0.0341 (16)	0.1534 (16)	0.017 (5)*
C9	0.3168 (2)	−0.13679 (15)	0.18290 (15)	0.0138 (4)
H9	0.218 (3)	−0.1537 (15)	0.1347 (15)	0.011 (5)*
C11	0.4380 (2)	−0.13701 (15)	0.36692 (15)	0.0128 (4)
H11	0.413 (3)	−0.1419 (16)	0.4292 (16)	0.017 (5)*
N1	0.6476 (2)	−0.29880 (13)	0.14577 (13)	0.0187 (4)
N2	0.56883 (19)	−0.21303 (12)	0.17848 (12)	0.0144 (4)
N3	0.78692 (19)	−0.19912 (13)	0.39526 (13)	0.0168 (4)
N4	0.70805 (19)	−0.11377 (12)	0.33725 (12)	0.0138 (3)
N5	0.4507 (2)	0.10364 (12)	0.30450 (13)	0.0155 (4)
N6	0.55269 (19)	0.02294 (12)	0.29645 (12)	0.0126 (3)
N7	0.3132 (2)	−0.01169 (13)	0.03827 (12)	0.0176 (4)
N8	0.38946 (19)	−0.05407 (13)	0.13608 (12)	0.0148 (4)
N9	0.1505 (2)	−0.10646 (13)	0.30242 (14)	0.0185 (4)
N10	0.30240 (19)	−0.09690 (13)	0.28396 (12)	0.0135 (3)
N11	0.4182 (2)	−0.33230 (13)	0.37287 (13)	0.0173 (4)
N12	0.4731 (2)	−0.24137 (12)	0.32882 (12)	0.0134 (3)
O1	0.58986 (19)	−0.38730 (11)	0.14617 (13)	0.0297 (4)
O2	0.76277 (18)	−0.27567 (12)	0.11731 (11)	0.0229 (3)
O3	0.84850 (18)	−0.26291 (11)	0.35006 (11)	0.0226 (3)
O4	0.79001 (18)	−0.20093 (12)	0.48790 (11)	0.0240 (3)
O5	0.42133 (17)	0.11261 (11)	0.38900 (10)	0.0196 (3)
O6	0.40305 (17)	0.16120 (10)	0.22807 (11)	0.0188 (3)
O7	0.19062 (19)	−0.05483 (12)	−0.01069 (11)	0.0287 (4)
O8	0.37638 (18)	0.06450 (11)	0.00893 (11)	0.0207 (3)
O9	0.03745 (17)	−0.11666 (11)	0.22556 (12)	0.0230 (3)
O10	0.15030 (19)	−0.09702 (12)	0.39345 (12)	0.0289 (4)
O11	0.40164 (19)	−0.32067 (11)	0.45951 (11)	0.0245 (4)
O12	0.40215 (17)	−0.41404 (11)	0.32126 (11)	0.0214 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0137 (10)	0.0142 (10)	0.0118 (10)	−0.0014 (8)	0.0035 (8)	−0.0018 (8)
C3	0.0145 (10)	0.0154 (10)	0.0117 (10)	−0.0005 (8)	0.0033 (8)	0.0006 (8)
C5	0.0166 (10)	0.0158 (10)	0.0106 (10)	−0.0005 (8)	0.0031 (8)	−0.0004 (8)
C7	0.0137 (10)	0.0155 (9)	0.0119 (10)	−0.0020 (8)	0.0036 (8)	0.0001 (8)
C9	0.0124 (10)	0.0160 (9)	0.0125 (10)	−0.0005 (8)	0.0026 (8)	−0.0003 (8)
C11	0.0128 (10)	0.0141 (9)	0.0118 (10)	0.0008 (8)	0.0038 (8)	0.0001 (7)
N1	0.0208 (9)	0.0190 (9)	0.0163 (9)	0.0055 (8)	0.0053 (7)	−0.0015 (7)
N2	0.0155 (9)	0.0146 (8)	0.0144 (9)	−0.0007 (7)	0.0064 (7)	−0.0038 (7)
N3	0.0134 (8)	0.0200 (9)	0.0154 (9)	0.0014 (7)	0.0018 (7)	0.0017 (7)
N4	0.0126 (8)	0.0153 (8)	0.0133 (8)	0.0022 (7)	0.0034 (7)	0.0012 (7)
N5	0.0146 (8)	0.0149 (8)	0.0173 (9)	−0.0033 (7)	0.0047 (7)	−0.0017 (7)
N6	0.0147 (8)	0.0104 (8)	0.0131 (8)	0.0012 (7)	0.0049 (7)	−0.0003 (6)
N7	0.0200 (10)	0.0205 (9)	0.0122 (9)	0.0061 (8)	0.0044 (7)	0.0000 (7)
N8	0.0139 (9)	0.0189 (8)	0.0098 (8)	−0.0007 (7)	0.0004 (7)	0.0035 (7)
N9	0.0177 (9)	0.0155 (9)	0.0246 (10)	0.0010 (7)	0.0099 (8)	0.0040 (7)
N10	0.0111 (8)	0.0175 (8)	0.0129 (8)	0.0015 (7)	0.0050 (6)	0.0016 (6)
N11	0.0155 (9)	0.0163 (8)	0.0203 (9)	−0.0010 (7)	0.0056 (7)	0.0027 (7)
N12	0.0166 (9)	0.0113 (8)	0.0134 (8)	−0.0007 (7)	0.0062 (7)	0.0002 (6)
O1	0.0284 (9)	0.0158 (8)	0.0488 (10)	−0.0013 (7)	0.0173 (8)	−0.0065 (7)
O2	0.0207 (8)	0.0287 (8)	0.0232 (8)	0.0055 (7)	0.0128 (7)	0.0013 (6)
O3	0.0225 (8)	0.0243 (8)	0.0231 (8)	0.0094 (7)	0.0097 (6)	0.0022 (6)
O4	0.0289 (9)	0.0294 (8)	0.0120 (7)	0.0057 (7)	0.0033 (6)	0.0040 (6)
O5	0.0228 (8)	0.0232 (8)	0.0155 (7)	0.0008 (6)	0.0096 (6)	−0.0044 (6)
O6	0.0192 (8)	0.0162 (7)	0.0212 (8)	0.0005 (6)	0.0062 (6)	0.0040 (6)
O7	0.0254 (9)	0.0324 (9)	0.0201 (8)	−0.0034 (7)	−0.0068 (7)	−0.0009 (7)
O8	0.0254 (8)	0.0215 (8)	0.0171 (8)	0.0040 (7)	0.0088 (6)	0.0074 (6)
O9	0.0132 (7)	0.0222 (8)	0.0330 (9)	−0.0019 (6)	0.0057 (7)	0.0036 (7)
O10	0.0272 (9)	0.0410 (10)	0.0247 (9)	0.0053 (8)	0.0175 (7)	0.0025 (7)
O11	0.0341 (9)	0.0233 (8)	0.0209 (8)	−0.0003 (7)	0.0158 (7)	0.0035 (6)
O12	0.0227 (8)	0.0138 (7)	0.0256 (8)	−0.0020 (6)	0.0038 (6)	−0.0028 (6)

Geometric parameters (Å, º)

C1—N2	1.438 (2)	C11—H11	0.92 (2)
C1—N12	1.477 (2)	N1—O2	1.214 (2)
C1—C9	1.574 (3)	N1—O1	1.218 (2)
C1—H1	0.90 (2)	N1—N2	1.411 (2)
C3—N2	1.446 (2)	N3—O3	1.215 (2)
C3—N4	1.480 (2)	N3—O4	1.225 (2)
C3—C7	1.573 (3)	N3—N4	1.381 (2)
C3—H3	0.96 (2)	N5—O6	1.218 (2)
C5—N6	1.455 (2)	N5—O5	1.228 (2)
C5—N4	1.458 (2)	N5—N6	1.375 (2)
C5—C11	1.587 (3)	N7—O7	1.215 (2)
C5—H5	0.96 (2)	N7—O8	1.222 (2)
C7—N8	1.441 (2)	N7—N8	1.387 (2)
C7—N6	1.465 (2)	N9—O9	1.212 (2)
C7—H7	0.94 (2)	N9—O10	1.217 (2)
C9—N8	1.447 (2)	N9—N10	1.431 (2)
C9—N10	1.472 (2)	N11—O11	1.211 (2)
C9—H9	0.94 (2)	N11—O12	1.216 (2)
C11—N10	1.463 (2)	N11—N12	1.425 (2)
C11—N12	1.464 (2)
N2—C1—N12	111.36 (16)	O2—N1—O1	127.17 (17)
N2—C1—C9	107.49 (15)	O2—N1—N2	116.28 (16)
N12—C1—C9	104.70 (15)	O1—N1—N2	116.50 (17)
N2—C1—H1	108.8 (13)	N1—N2—C1	118.76 (15)
N12—C1—H1	109.9 (13)	N1—N2—C3	118.34 (15)
C9—C1—H1	114.6 (13)	C1—N2—C3	117.04 (15)
N2—C3—N4	113.92 (15)	O3—N3—O4	126.91 (17)
N2—C3—C7	108.06 (15)	O3—N3—N4	117.02 (15)
N4—C3—C7	101.11 (14)	O4—N3—N4	116.04 (15)
N2—C3—H3	108.0 (11)	N3—N4—C5	117.03 (14)
N4—C3—H3	111.2 (12)	N3—N4—C3	119.88 (14)
C7—C3—H3	114.5 (11)	C5—N4—C3	110.82 (15)
N6—C5—N4	95.64 (14)	O6—N5—O5	126.70 (17)
N6—C5—C11	112.92 (16)	O6—N5—N6	116.42 (15)
N4—C5—C11	112.56 (15)	O5—N5—N6	116.82 (15)
N6—C5—H5	112.5 (13)	N5—N6—C5	118.79 (15)
N4—C5—H5	111.6 (13)	N5—N6—C7	119.19 (15)
C11—C5—H5	110.9 (13)	C5—N6—C7	111.12 (14)
N8—C7—N6	111.74 (16)	O7—N7—O8	126.17 (17)
N8—C7—C3	109.38 (15)	O7—N7—N8	116.76 (16)
N6—C7—C3	101.83 (14)	O8—N7—N8	117.06 (16)
N8—C7—H7	109.4 (13)	N7—N8—C7	120.47 (15)
N6—C7—H7	109.7 (12)	N7—N8—C9	121.44 (16)
C3—C7—H7	114.7 (13)	C7—N8—C9	118.05 (15)
N8—C9—N10	108.35 (16)	O9—N9—O10	127.91 (18)
N8—C9—C1	109.89 (15)	O9—N9—N10	116.47 (16)
N10—C9—C1	104.40 (14)	O10—N9—N10	115.46 (17)
N8—C9—H9	107.6 (12)	N9—N10—C11	116.27 (14)
N10—C9—H9	113.1 (12)	N9—N10—C9	117.17 (15)
C1—C9—H9	113.4 (12)	C11—N10—C9	107.91 (15)
N10—C11—N12	104.57 (15)	O11—N11—O12	127.72 (16)
N10—C11—C5	108.92 (15)	O11—N11—N12	116.27 (15)
N12—C11—C5	107.48 (15)	O12—N11—N12	115.86 (16)
N10—C11—H11	110.6 (13)	N11—N12—C11	116.02 (15)
N12—C11—H11	112.4 (13)	N11—N12—C1	117.08 (15)
C5—C11—H11	112.5 (13)	C11—N12—C1	107.66 (15)

(100eHNIW)

Crystal data

C6H6N12O12	F(000) = 888
Mr = 438.23	Dx = 2.083 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.7910 (18) Å	Cell parameters from 3033 reflections
b = 12.481 (3) Å	θ = 4.6–58.3°
c = 13.285 (3) Å	µ = 0.20 mm^−1
β = 106.55 (3)°	T = 100 K
V = 1397.2 (5) Å^3	Block, colorless
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection

Radiation source: fine-focus sealed tube	2666 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
Absorption correction: empirical Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany	θmax = 29.8°, θmin = 2.3°
Tmin = 0.936, Tmax = 1.000	h = −12→10
9849 measured reflections	k = −15→17
3651 independent reflections	l = −18→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.092	w = 1/[σ^2(Fo^2) + (0.0372P)^2 + 0.6042P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.112
3651 reflections	Δρmax = 0.37 e Å^−3
296 parameters	Δρmin = −0.32 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0065 (9)

Special details

Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS. No formal measure of the extent of decay is printed out by this program. The final unit cell is obtained from the refinement of the XYZ weighted centroids of reflections above 15 σ(I).

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.4318 (2)	−0.23594 (15)	0.21295 (14)	0.0097 (4)
H1	0.386 (2)	−0.3002 (17)	0.1853 (16)	0.012 (5)*
C3	0.6608 (2)	−0.11870 (14)	0.22128 (14)	0.0107 (4)
H3	0.748 (2)	−0.1154 (14)	0.1950 (14)	0.006 (5)*
C5	0.5867 (2)	−0.06174 (14)	0.37491 (15)	0.0101 (4)
H5	0.626 (2)	−0.0337 (15)	0.4414 (15)	0.002 (4)*
C7	0.5471 (2)	−0.01879 (14)	0.19224 (14)	0.0099 (4)
H7	0.584 (2)	0.0322 (16)	0.1536 (16)	0.012 (5)*
C9	0.3167 (2)	−0.13679 (14)	0.18275 (14)	0.0101 (4)
H9	0.215 (2)	−0.1538 (14)	0.1343 (14)	0.000 (4)*
C11	0.4376 (2)	−0.13737 (14)	0.36686 (14)	0.0098 (4)
H11	0.418 (2)	−0.1410 (15)	0.4300 (15)	0.003 (4)*
N1	0.64823 (19)	−0.29931 (12)	0.14541 (12)	0.0139 (3)
N2	0.56941 (17)	−0.21328 (12)	0.17818 (12)	0.0111 (3)
N3	0.78711 (18)	−0.19951 (12)	0.39532 (12)	0.0128 (3)
N4	0.70831 (18)	−0.11394 (12)	0.33713 (12)	0.0105 (3)
N5	0.45091 (18)	0.10406 (12)	0.30470 (12)	0.0113 (3)
N6	0.55296 (18)	0.02314 (11)	0.29666 (11)	0.0097 (3)
N7	0.31335 (18)	−0.01129 (12)	0.03787 (12)	0.0123 (3)
N8	0.39019 (18)	−0.05405 (12)	0.13583 (12)	0.0109 (3)
N9	0.14986 (18)	−0.10703 (12)	0.30257 (13)	0.0133 (3)
N10	0.30229 (17)	−0.09702 (12)	0.28399 (11)	0.0105 (3)
N11	0.41827 (18)	−0.33289 (12)	0.37300 (12)	0.0131 (3)
N12	0.47317 (18)	−0.24187 (11)	0.32874 (11)	0.0100 (3)
O1	0.59001 (17)	−0.38801 (11)	0.14527 (12)	0.0225 (3)
O2	0.76376 (16)	−0.27594 (11)	0.11673 (10)	0.0166 (3)
O3	0.84853 (16)	−0.26379 (10)	0.34949 (10)	0.0164 (3)
O4	0.79028 (16)	−0.20162 (11)	0.48817 (10)	0.0177 (3)
O5	0.42046 (16)	0.11271 (10)	0.38926 (10)	0.0150 (3)
O6	0.40260 (15)	0.16107 (10)	0.22766 (10)	0.0140 (3)
O7	0.19078 (17)	−0.05467 (11)	−0.01134 (11)	0.0211 (3)
O8	0.37694 (16)	0.06506 (10)	0.00896 (10)	0.0153 (3)
O9	0.03681 (15)	−0.11716 (10)	0.22562 (11)	0.0168 (3)
O10	0.14941 (17)	−0.09752 (12)	0.39367 (11)	0.0220 (3)
O11	0.40149 (17)	−0.32144 (11)	0.45976 (10)	0.0180 (3)
O12	0.40197 (16)	−0.41481 (10)	0.32114 (10)	0.0159 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0099 (8)	0.0106 (9)	0.0095 (9)	−0.0005 (7)	0.0043 (7)	−0.0006 (7)
C3	0.0099 (9)	0.0120 (9)	0.0102 (9)	0.0006 (7)	0.0028 (7)	0.0007 (7)
C5	0.0105 (9)	0.0103 (9)	0.0092 (9)	0.0015 (7)	0.0025 (7)	−0.0001 (7)
C7	0.0091 (8)	0.0129 (9)	0.0078 (9)	−0.0001 (7)	0.0027 (7)	0.0005 (7)
C9	0.0094 (9)	0.0104 (8)	0.0102 (9)	−0.0010 (7)	0.0025 (7)	0.0001 (7)
C11	0.0114 (9)	0.0103 (8)	0.0079 (9)	0.0007 (7)	0.0031 (7)	−0.0001 (7)
N1	0.0145 (8)	0.0151 (8)	0.0117 (8)	0.0040 (7)	0.0029 (6)	−0.0011 (6)
N2	0.0100 (7)	0.0116 (7)	0.0127 (8)	0.0001 (6)	0.0047 (6)	−0.0026 (6)
N3	0.0095 (7)	0.0142 (8)	0.0142 (8)	0.0001 (6)	0.0025 (6)	0.0010 (6)
N4	0.0102 (7)	0.0111 (7)	0.0099 (7)	0.0020 (6)	0.0024 (6)	0.0006 (6)
N5	0.0089 (7)	0.0109 (7)	0.0140 (8)	−0.0024 (6)	0.0030 (6)	−0.0010 (6)
N6	0.0110 (7)	0.0082 (7)	0.0102 (7)	0.0011 (6)	0.0037 (6)	0.0001 (6)
N7	0.0131 (8)	0.0141 (8)	0.0094 (8)	0.0046 (7)	0.0025 (6)	−0.0008 (6)
N8	0.0098 (7)	0.0140 (8)	0.0076 (7)	−0.0007 (6)	0.0003 (6)	0.0022 (6)
N9	0.0107 (8)	0.0115 (8)	0.0198 (9)	0.0008 (6)	0.0079 (7)	0.0024 (6)
N10	0.0073 (7)	0.0136 (8)	0.0112 (8)	−0.0004 (6)	0.0038 (6)	0.0000 (6)
N11	0.0104 (8)	0.0124 (8)	0.0164 (8)	0.0002 (6)	0.0037 (6)	0.0031 (6)
N12	0.0115 (7)	0.0091 (7)	0.0097 (8)	−0.0011 (6)	0.0037 (6)	0.0006 (6)
O1	0.0219 (8)	0.0126 (7)	0.0358 (9)	−0.0011 (6)	0.0127 (7)	−0.0042 (6)
O2	0.0150 (7)	0.0210 (7)	0.0166 (7)	0.0028 (6)	0.0089 (6)	0.0010 (6)
O3	0.0145 (7)	0.0188 (7)	0.0171 (7)	0.0064 (6)	0.0064 (6)	0.0015 (6)
O4	0.0197 (7)	0.0220 (7)	0.0101 (7)	0.0037 (6)	0.0021 (5)	0.0027 (6)
O5	0.0169 (7)	0.0169 (7)	0.0129 (7)	0.0001 (6)	0.0071 (5)	−0.0032 (5)
O6	0.0131 (7)	0.0129 (6)	0.0160 (7)	0.0004 (5)	0.0039 (5)	0.0031 (5)
O7	0.0175 (7)	0.0233 (8)	0.0165 (7)	−0.0024 (6)	−0.0050 (6)	−0.0010 (6)
O8	0.0179 (7)	0.0152 (7)	0.0144 (7)	0.0022 (6)	0.0073 (6)	0.0051 (5)
O9	0.0093 (6)	0.0162 (7)	0.0239 (8)	−0.0004 (6)	0.0034 (6)	0.0026 (6)
O10	0.0211 (8)	0.0296 (8)	0.0198 (8)	0.0035 (7)	0.0131 (6)	0.0015 (6)
O11	0.0242 (8)	0.0180 (7)	0.0153 (7)	0.0000 (6)	0.0113 (6)	0.0032 (5)
O12	0.0164 (7)	0.0104 (6)	0.0194 (7)	−0.0008 (5)	0.0027 (6)	−0.0010 (5)

Geometric parameters (Å, º)

C1—N2	1.441 (2)	N1—N2	1.412 (2)
C1—N12	1.478 (2)	N3—O3	1.222 (2)
C1—C9	1.576 (3)	N3—O4	1.226 (2)
C3—N2	1.451 (2)	N3—N4	1.383 (2)
C3—N4	1.477 (2)	N5—O6	1.2191 (19)
C3—C7	1.576 (3)	N5—O5	1.2315 (19)
C5—N6	1.454 (2)	N5—N6	1.375 (2)
C5—N4	1.458 (2)	N7—O7	1.217 (2)
C5—C11	1.593 (3)	N7—O8	1.221 (2)
C7—N8	1.439 (2)	N7—N8	1.391 (2)
C7—N6	1.470 (2)	N9—O9	1.212 (2)
C9—N8	1.450 (2)	N9—O10	1.217 (2)
C9—N10	1.473 (2)	N9—N10	1.435 (2)
C11—N10	1.461 (2)	N11—O11	1.211 (2)
C11—N12	1.465 (2)	N11—O12	1.218 (2)
N1—O2	1.217 (2)	N11—N12	1.425 (2)
N1—O1	1.219 (2)
N2—C1—N12	111.28 (15)	N3—N4—C5	116.89 (14)
N2—C1—C9	107.52 (14)	N3—N4—C3	119.96 (14)
N12—C1—C9	104.72 (14)	C5—N4—C3	111.06 (14)
N2—C3—N4	113.86 (14)	O6—N5—O5	126.90 (16)
N2—C3—C7	107.82 (14)	O6—N5—N6	116.25 (14)
N4—C3—C7	101.23 (13)	O5—N5—N6	116.83 (15)
N6—C5—N4	95.71 (13)	N5—N6—C5	118.95 (14)
N6—C5—C11	112.78 (15)	N5—N6—C7	119.12 (14)
N4—C5—C11	112.44 (14)	C5—N6—C7	111.13 (13)
N8—C7—N6	111.78 (14)	O7—N7—O8	126.38 (16)
N8—C7—C3	109.43 (15)	O7—N7—N8	116.86 (15)
N6—C7—C3	101.63 (13)	O8—N7—N8	116.75 (15)
N8—C9—N10	108.50 (14)	N7—N8—C7	120.54 (14)
N8—C9—C1	109.65 (14)	N7—N8—C9	121.23 (14)
N10—C9—C1	104.36 (14)	C7—N8—C9	118.21 (15)
N10—C11—N12	104.74 (14)	O9—N9—O10	127.91 (16)
N10—C11—C5	108.90 (14)	O9—N9—N10	116.44 (14)
N12—C11—C5	107.37 (14)	O10—N9—N10	115.47 (15)
O2—N1—O1	127.17 (16)	N9—N10—C11	116.12 (14)
O2—N1—N2	116.15 (15)	N9—N10—C9	117.07 (14)
O1—N1—N2	116.62 (15)	C11—N10—C9	107.97 (14)
N1—N2—C1	118.70 (14)	O11—N11—O12	127.62 (16)
N1—N2—C3	118.37 (14)	O11—N11—N12	116.48 (15)
C1—N2—C3	117.03 (14)	O12—N11—N12	115.77 (15)
O3—N3—O4	126.91 (16)	N11—N12—C11	115.89 (14)
O3—N3—N4	116.78 (15)	N11—N12—C1	117.21 (14)
O4—N3—N4	116.30 (14)	C11—N12—C1	107.56 (14)