10,10′-Dinitro-10,10′-(propane-1,3-di­yl)di-10H-anthracen-9-one

The title compound, C₃₁H₂₂N₂O₆, was obtained as the decomposition product of (E,E)-1,3-bis­[9,10-dihydro-9-nitro-10-(trinitro­meth­yl)-9-anthr­yl]propane, which was synthesized via a photochemical reaction of 1,3-di-9-anthrylpropane with tetra­nitro­methane. Inter­molecular C—H...O inter­actions are the most prominent features of the crystal packing; no indications of any inter­molecular π–π stacking were found.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.076
• wR factor = 0.214
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for          N

Alert level C
ABSMU01_ALERT_1_C  The ratio of given/expected absorption coefficient lies
               outside the range 0.99 <> 1.01
            Calculated value of mu =     0.094
            Value of mu given      =     0.090
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         42 Perc.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.87 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N'
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2'    ..  O2      ..       2.67 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5     ..  O2'     ..       2.69 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C31 H22 N2 O6

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4-PC Software (Enraf–Nonius, 1993); cell refinement: CAD-4-PC Software; data reduction: DATRD2 in NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

10,10'-Dinitro-10,10'-(propane-1,3-diyl)di-10H-anthracen-9-one

Crystal data

C31H22N2O6	F(000) = 1080
Mr = 518.51	Dx = 1.343 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 13.438 (2) Å	θ = 20.0–25.0°
b = 14.490 (3) Å	µ = 0.09 mm^−1
c = 13.974 (3) Å	T = 295 K
β = 109.505 (5)°	Plate, yellow
V = 2564.8 (9) Å^3	0.32 × 0.29 × 0.13 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	θmax = 25.1°, θmin = 1.8°
Radiation source: fine-focus sealed tube	h = −16→15
Graphite monochromator	k = 0→17
ω scans	l = 0→16
4554 measured reflections	3 standard reflections every 120 min
4554 independent reflections	intensity decay: 1.1%
1912 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.214	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0908P)^2] where P = (Fo^2 + 2Fc^2)/3
4554 reflections	(Δ/σ)max < 0.001
352 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 5.8565 (0.0154) x + 10.3861 (0.0066) y + 9.2033 (0.0075) z = 17.9254 (0.0211)

* -0.0234 (0.0052) C1 * -0.0282 (0.0055) C2 * -0.0125 (0.0048) C3 * 0.0026 (0.0042) C4 * 0.0010 (0.0041) C4A * 0.0619 (0.0051) C9 * 0.0188 (0.0045) C9A * 0.0040 (0.0044) C5 * -0.0197 (0.0055) C6 * -0.0305 (0.0061) C7 * -0.0112 (0.0052) C8 * 0.0123 (0.0047) C8A * 0.0166 (0.0038) C10 * 0.0082 (0.0041) C10A

Rms deviation of fitted atoms = 0.0234

- 0.9842 (0.0157) x + 10.4475 (0.0062) y + 9.4178 (0.0062) z = 16.7212 (0.0108)

Angle to previous plane (with approximate e.s.d.) = 22.51 (0.09)

* -0.0210 (0.0045) C1' * -0.0326 (0.0051) C2' * -0.0045 (0.0051) C3' * 0.0151 (0.0044) C4' * 0.0173 (0.0040) C4A' * 0.0286 (0.0044) C9' * -0.0024 (0.0043) C9A' * -0.0179 (0.0040) C5' * -0.0349 (0.0045) C6' * -0.0037 (0.0051) C7' * 0.0157 (0.0047) C8' * 0.0198 (0.0043) C8A' * 0.0273 (0.0036) C10' * -0.0066 (0.0039) C10A'

Rms deviation of fitted atoms = 0.0204

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
O1	0.6501 (3)	0.8155 (3)	1.6982 (3)	0.0824 (12)
O2	0.5262 (3)	0.7478 (4)	1.5921 (4)	0.142 (2)
O9	1.0146 (3)	0.7358 (4)	1.7797 (3)	0.1274 (19)
O1'	0.6649 (3)	0.3216 (2)	1.2418 (3)	0.0724 (11)
O2'	0.5424 (3)	0.4161 (3)	1.2316 (3)	0.0997 (16)
O9'	1.0343 (2)	0.4184 (3)	1.4236 (3)	0.0900 (13)
N	0.6169 (3)	0.7578 (3)	1.6353 (3)	0.0570 (11)
N'	0.6317 (3)	0.3880 (3)	1.2705 (3)	0.0494 (10)
C1	0.9345 (5)	0.8340 (4)	1.5986 (5)	0.0827 (19)
H1	1.0061	0.8399	1.6348	0.099*
C2	0.8909 (7)	0.8850 (5)	1.5129 (6)	0.096 (2)
H2	0.9319	0.9261	1.491	0.115*
C3	0.7871 (6)	0.8747 (4)	1.4601 (5)	0.0799 (18)
H3	0.7568	0.9095	1.4017	0.096*
C4	0.7256 (4)	0.8143 (3)	1.4907 (4)	0.0574 (14)
H4	0.6543	0.8086	1.453	0.069*
C4A	0.7685 (3)	0.7619 (3)	1.5770 (3)	0.0411 (11)
C5	0.6958 (4)	0.5779 (4)	1.7388 (4)	0.0656 (15)
H5	0.6242	0.5698	1.7038	0.079*
C6	0.7437 (7)	0.5267 (4)	1.8245 (5)	0.092 (2)
H6	0.7043	0.4841	1.8464	0.11*
C7	0.8480 (8)	0.5374 (5)	1.8775 (5)	0.103 (2)
H7	0.8798	0.5022	1.9353	0.124*
C8	0.9049 (5)	0.5995 (5)	1.8458 (4)	0.0848 (19)
H8	0.9763	0.6071	1.8824	0.102*
C8A	0.8586 (4)	0.6524 (4)	1.7592 (4)	0.0556 (13)
C9	0.9224 (4)	0.7210 (4)	1.7277 (4)	0.0718 (17)
C9A	0.8730 (3)	0.7727 (3)	1.6333 (3)	0.0518 (13)
C10	0.6986 (3)	0.6962 (3)	1.6083 (3)	0.0381 (11)
C10A	0.7531 (3)	0.6415 (3)	1.7039 (3)	0.0435 (11)
C11	0.6376 (3)	0.6339 (3)	1.5206 (3)	0.0441 (12)
H11A	0.5894	0.5958	1.5419	0.053*
H11B	0.5957	0.6719	1.4644	0.053*
C12	0.7094 (3)	0.5715 (3)	1.4842 (3)	0.0418 (11)
H12A	0.7567	0.6091	1.461	0.05*
H12B	0.7519	0.5334	1.5399	0.05*
C1'	0.9300 (4)	0.5421 (4)	1.2691 (4)	0.0679 (16)
H1'	1.0024	0.5352	1.2839	0.082*
C2'	0.8775 (6)	0.6013 (4)	1.1967 (5)	0.0849 (19)
H2'	0.913	0.6343	1.1609	0.102*
C3'	0.7724 (6)	0.6132 (4)	1.1755 (5)	0.0814 (18)
H3'	0.7363	0.6552	1.1257	0.098*
C4'	0.7186 (4)	0.5642 (3)	1.2263 (4)	0.0600 (14)
H4'	0.6463	0.5729	1.2104	0.072*
C4A'	0.7704 (3)	0.5023 (3)	1.3006 (3)	0.0394 (11)
C5'	0.7235 (4)	0.3268 (3)	1.4867 (4)	0.0540 (13)
H5'	0.6512	0.3324	1.4734	0.065*
C6'	0.7817 (6)	0.2653 (4)	1.5591 (4)	0.0745 (17)
H6'	0.7474	0.2285	1.5929	0.089*
C7'	0.8884 (6)	0.2574 (4)	1.5824 (4)	0.086 (2)
H7'	0.9267	0.2166	1.6326	0.103*
C8'	0.9381 (5)	0.3100 (4)	1.5314 (4)	0.0706 (16)
H8'	1.0107	0.3042	1.5464	0.085*
C8A'	0.8822 (3)	0.3719 (3)	1.4572 (3)	0.0469 (12)
C9'	0.9391 (4)	0.4265 (4)	1.4035 (4)	0.0564 (14)
C9A'	0.8788 (3)	0.4903 (3)	1.3231 (4)	0.0465 (12)
C10'	0.7091 (3)	0.4481 (3)	1.3555 (3)	0.0361 (10)
C10A'	0.7731 (3)	0.3801 (3)	1.4339 (3)	0.0390 (11)
C11'	0.6434 (3)	0.5108 (3)	1.3983 (3)	0.0421 (11)
H11C	0.5993	0.5496	1.3443	0.051*
H11D	0.5973	0.473	1.4227	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.079 (3)	0.080 (3)	0.096 (3)	0.003 (2)	0.039 (2)	−0.036 (3)
O2	0.043 (2)	0.185 (5)	0.190 (5)	0.008 (3)	0.030 (3)	−0.109 (4)
O9	0.057 (3)	0.201 (5)	0.094 (3)	−0.048 (3)	−0.014 (2)	0.012 (3)
O1'	0.084 (3)	0.057 (2)	0.071 (3)	−0.004 (2)	0.019 (2)	−0.028 (2)
O2'	0.044 (2)	0.119 (4)	0.114 (3)	0.002 (2)	−0.002 (2)	−0.056 (3)
O9'	0.0311 (19)	0.118 (3)	0.121 (3)	0.010 (2)	0.025 (2)	−0.002 (3)
N	0.044 (3)	0.067 (3)	0.063 (3)	0.004 (2)	0.023 (2)	−0.015 (2)
N'	0.049 (3)	0.047 (3)	0.052 (3)	−0.005 (2)	0.015 (2)	−0.012 (2)
C1	0.069 (4)	0.096 (5)	0.086 (5)	−0.042 (4)	0.030 (4)	−0.024 (4)
C2	0.119 (6)	0.085 (5)	0.111 (6)	−0.041 (5)	0.074 (5)	−0.010 (5)
C3	0.117 (5)	0.068 (4)	0.071 (4)	0.005 (4)	0.054 (4)	0.010 (3)
C4	0.063 (3)	0.060 (3)	0.053 (3)	−0.001 (3)	0.024 (3)	0.003 (3)
C4A	0.040 (2)	0.049 (3)	0.036 (3)	−0.001 (2)	0.016 (2)	−0.006 (2)
C5	0.071 (3)	0.068 (4)	0.063 (4)	−0.010 (3)	0.029 (3)	0.001 (3)
C6	0.134 (6)	0.065 (4)	0.088 (5)	−0.011 (4)	0.054 (5)	0.011 (4)
C7	0.153 (8)	0.080 (5)	0.071 (5)	0.017 (5)	0.029 (5)	0.032 (4)
C8	0.083 (4)	0.096 (5)	0.060 (4)	0.024 (4)	0.003 (3)	0.016 (4)
C8A	0.046 (3)	0.065 (3)	0.048 (3)	0.005 (3)	0.006 (2)	−0.001 (3)
C9	0.039 (3)	0.103 (5)	0.063 (4)	−0.016 (3)	0.003 (3)	−0.009 (3)
C9A	0.043 (3)	0.063 (3)	0.051 (3)	−0.019 (3)	0.018 (2)	−0.011 (3)
C10	0.028 (2)	0.045 (3)	0.043 (3)	0.002 (2)	0.015 (2)	−0.008 (2)
C10A	0.042 (3)	0.047 (3)	0.045 (3)	0.002 (2)	0.019 (2)	−0.006 (2)
C11	0.028 (2)	0.054 (3)	0.053 (3)	−0.001 (2)	0.015 (2)	−0.010 (2)
C12	0.031 (2)	0.051 (3)	0.046 (3)	−0.005 (2)	0.016 (2)	−0.014 (2)
C1'	0.063 (4)	0.074 (4)	0.082 (4)	−0.015 (3)	0.044 (3)	−0.009 (3)
C2'	0.109 (5)	0.072 (4)	0.099 (5)	−0.026 (4)	0.068 (5)	0.004 (4)
C3'	0.111 (5)	0.059 (4)	0.081 (4)	0.006 (4)	0.042 (4)	0.026 (3)
C4'	0.059 (3)	0.053 (3)	0.073 (4)	0.005 (3)	0.028 (3)	0.019 (3)
C4A'	0.037 (2)	0.036 (3)	0.045 (3)	−0.001 (2)	0.014 (2)	−0.002 (2)
C5'	0.061 (3)	0.054 (3)	0.053 (3)	0.000 (3)	0.028 (3)	0.006 (3)
C6'	0.114 (5)	0.055 (4)	0.059 (4)	0.008 (4)	0.035 (4)	0.012 (3)
C7'	0.111 (5)	0.076 (5)	0.056 (4)	0.037 (4)	0.010 (4)	0.017 (3)
C8'	0.066 (4)	0.072 (4)	0.065 (4)	0.025 (3)	0.009 (3)	0.005 (3)
C8A'	0.039 (3)	0.050 (3)	0.047 (3)	0.010 (2)	0.008 (2)	−0.001 (2)
C9'	0.034 (3)	0.066 (4)	0.069 (3)	0.003 (3)	0.018 (3)	−0.013 (3)
C9A'	0.041 (3)	0.046 (3)	0.059 (3)	−0.006 (2)	0.026 (2)	−0.006 (3)
C10'	0.030 (2)	0.039 (3)	0.038 (2)	−0.007 (2)	0.0104 (19)	−0.011 (2)
C10A'	0.041 (2)	0.037 (3)	0.040 (3)	0.003 (2)	0.013 (2)	−0.003 (2)
C11'	0.032 (2)	0.049 (3)	0.046 (3)	−0.004 (2)	0.015 (2)	−0.004 (2)

Geometric parameters (Å, º)

O1—N	1.187 (5)	C11—C12	1.528 (5)
O2—N	1.175 (5)	C11—H11A	0.97
O9—C9	1.228 (5)	C11—H11B	0.97
O1'—N'	1.185 (4)	C12—C11'	1.514 (5)
O2'—N'	1.210 (5)	C12—H12A	0.97
O9'—C9'	1.221 (5)	C12—H12B	0.97
N—C10	1.554 (5)	C1'—C2'	1.334 (8)
N'—C10'	1.558 (5)	C1'—C9A'	1.398 (6)
C1—C2	1.362 (8)	C1'—H1'	0.93
C1—C9A	1.405 (7)	C2'—C3'	1.354 (8)
C1—H1	0.93	C2'—H2'	0.93
C2—C3	1.351 (8)	C3'—C4'	1.370 (7)
C2—H2	0.93	C3'—H3'	0.93
C3—C4	1.366 (7)	C4'—C4A'	1.372 (6)
C3—H3	0.93	C4'—H4'	0.93
C4—C4A	1.379 (6)	C4A'—C9A'	1.396 (5)
C4—H4	0.93	C4A'—C10'	1.519 (5)
C4A—C9A	1.371 (6)	C5'—C6'	1.378 (7)
C4A—C10	1.501 (6)	C5'—C10A'	1.384 (6)
C5—C6	1.371 (8)	C5'—H5'	0.93
C5—C10A	1.390 (6)	C6'—C7'	1.366 (8)
C5—H5	0.93	C6'—H6'	0.93
C6—C7	1.357 (9)	C7'—C8'	1.361 (8)
C6—H6	0.93	C7'—H7'	0.93
C7—C8	1.348 (8)	C8'—C8A'	1.387 (6)
C7—H7	0.93	C8'—H8'	0.93
C8—C8A	1.391 (7)	C8A'—C10A'	1.396 (6)
C8—H8	0.93	C8A'—C9'	1.469 (7)
C8A—C10A	1.380 (6)	C9'—C9A'	1.472 (6)
C8A—C9	1.473 (7)	C10'—C11'	1.522 (5)
C9—C9A	1.469 (7)	C10'—C10A'	1.510 (6)
C10—C10A	1.515 (6)	C11'—H11C	0.97
C10—C11	1.523 (5)	C11'—H11D	0.97
O1—N—O2	122.4 (4)	C11'—C12—C11	109.8 (3)
O1—N—C10	117.6 (4)	C11'—C12—H12A	109.7
O2—N—C10	120.0 (4)	C11—C12—H12A	109.7
O1'—N'—O2'	123.4 (4)	C11'—C12—H12B	109.7
O1'—N'—C10'	118.7 (4)	C11—C12—H12B	109.7
O2'—N'—C10'	117.6 (4)	H12A—C12—H12B	108.2
C2—C1—C9A	121.1 (6)	C2'—C1'—C9A'	121.6 (5)
C2—C1—H1	119.4	C2'—C1'—H1'	119.2
C9A—C1—H1	119.4	C9A'—C1'—H1'	119.2
C1—C2—C3	118.8 (6)	C1'—C2'—C3'	119.8 (6)
C1—C2—H2	120.6	C1'—C2'—H2'	120.1
C3—C2—H2	120.6	C3'—C2'—H2'	120.1
C2—C3—C4	121.5 (6)	C2'—C3'—C4'	120.9 (6)
C2—C3—H3	119.2	C2'—C3'—H3'	119.6
C4—C3—H3	119.2	C4'—C3'—H3'	119.6
C3—C4—C4A	120.4 (5)	C4A'—C4'—C3'	120.6 (5)
C3—C4—H4	119.8	C4A'—C4'—H4'	119.7
C4A—C4—H4	119.8	C3'—C4'—H4'	119.7
C9A—C4A—C4	119.2 (5)	C4'—C4A'—C9A'	118.7 (4)
C9A—C4A—C10	121.8 (4)	C4'—C4A'—C10'	119.8 (4)
C4—C4A—C10	119.0 (4)	C9A'—C4A'—C10'	121.5 (4)
C6—C5—C10A	120.8 (6)	C6'—C5'—C10A'	119.7 (5)
C6—C5—H5	119.6	C6'—C5'—H5'	120.1
C10A—C5—H5	119.6	C10A'—C5'—H5'	120.1
C7—C6—C5	120.9 (6)	C7'—C6'—C5'	121.5 (6)
C7—C6—H6	119.6	C7'—C6'—H6'	119.3
C5—C6—H6	119.6	C5'—C6'—H6'	119.3
C6—C7—C8	119.5 (6)	C6'—C7'—C8'	119.2 (6)
C6—C7—H7	120.3	C6'—C7'—H7'	120.4
C8—C7—H7	120.3	C8'—C7'—H7'	120.4
C7—C8—C8A	121.0 (6)	C7'—C8'—C8A'	121.0 (5)
C7—C8—H8	119.5	C7'—C8'—H8'	119.5
C8A—C8—H8	119.5	C8A'—C8'—H8'	119.5
C10A—C8A—C8	120.1 (5)	C10A'—C8A'—C8'	119.6 (5)
C10A—C8A—C9	120.1 (5)	C10A'—C8A'—C9'	121.3 (4)
C8—C8A—C9	119.8 (5)	C8'—C8A'—C9'	119.1 (5)
O9—C9—C9A	120.5 (5)	O9'—C9'—C9A'	120.2 (5)
O9—C9—C8A	120.9 (5)	O9'—C9'—C8A'	121.0 (5)
C9A—C9—C8A	118.7 (4)	C9A'—C9'—C8A'	118.8 (4)
C4A—C9A—C1	118.8 (5)	C4A'—C9A'—C1'	118.4 (5)
C4A—C9A—C9	121.8 (4)	C4A'—C9A'—C9'	121.2 (4)
C1—C9A—C9	119.4 (5)	C1'—C9A'—C9'	120.4 (5)
C4A—C10—C10A	115.1 (3)	C11'—C10'—C10A'	111.6 (4)
C4A—C10—C11	111.2 (4)	C11'—C10'—C4A'	111.9 (3)
C10A—C10—C11	111.7 (4)	C10A'—C10'—C4A'	115.5 (3)
C4A—C10—N	105.5 (3)	C11'—C10'—N'	107.9 (3)
C10A—C10—N	105.0 (3)	C10A'—C10'—N'	105.2 (3)
C11—C10—N	107.6 (3)	C4A'—C10'—N'	104.0 (3)
C5—C10A—C8A	117.7 (5)	C5'—C10A'—C8A'	118.9 (4)
C5—C10A—C10	119.7 (4)	C5'—C10A'—C10'	119.4 (4)
C8A—C10A—C10	122.6 (4)	C8A'—C10A'—C10'	121.6 (4)
C12—C11—C10	112.9 (3)	C12—C11'—C10'	113.3 (3)
C12—C11—H11A	109	C12—C11'—H11C	108.9
C10—C11—H11A	109	C10'—C11'—H11C	108.9
C12—C11—H11B	109	C12—C11'—H11D	108.9
C10—C11—H11B	109	C10'—C11'—H11D	108.9
H11A—C11—H11B	107.8	H11C—C11'—H11D	107.7
C9A—C1—C2—C3	−1.0 (10)	C9A'—C1'—C2'—C3'	1.1 (9)
C1—C2—C3—C4	−0.3 (10)	C1'—C2'—C3'—C4'	−1.0 (10)
C2—C3—C4—C4A	−0.1 (9)	C2'—C3'—C4'—C4A'	0.5 (9)
C3—C4—C4A—C9A	1.7 (7)	C3'—C4'—C4A'—C9A'	−0.1 (7)
C3—C4—C4A—C10	−179.9 (4)	C3'—C4'—C4A'—C10'	−179.5 (5)
C10A—C5—C6—C7	0.4 (9)	C10A'—C5'—C6'—C7'	1.8 (8)
C5—C6—C7—C8	0.3 (11)	C5'—C6'—C7'—C8'	−1.4 (9)
C6—C7—C8—C8A	−0.4 (11)	C6'—C7'—C8'—C8A'	0.7 (9)
C7—C8—C8A—C10A	−0.4 (9)	C7'—C8'—C8A'—C10A'	−0.5 (8)
C7—C8—C8A—C9	178.7 (6)	C7'—C8'—C8A'—C9'	−179.4 (5)
C10A—C8A—C9—O9	175.2 (5)	C10A'—C8A'—C9'—O9'	−179.3 (5)
C8—C8A—C9—O9	−3.8 (9)	C8'—C8A'—C9'—O9'	−0.4 (7)
C10A—C8A—C9—C9A	−3.9 (8)	C10A'—C8A'—C9'—C9A'	−0.5 (7)
C8—C8A—C9—C9A	177.0 (5)	C8'—C8A'—C9'—C9A'	178.4 (4)
C4—C4A—C9A—C1	−2.9 (7)	C4'—C4A'—C9A'—C1'	0.1 (7)
C10—C4A—C9A—C1	178.8 (4)	C10'—C4A'—C9A'—C1'	179.5 (4)
C4—C4A—C9A—C9	178.0 (5)	C4'—C4A'—C9A'—C9'	178.6 (4)
C10—C4A—C9A—C9	−0.4 (7)	C10'—C4A'—C9A'—C9'	−2.0 (6)
C2—C1—C9A—C4A	2.6 (9)	C2'—C1'—C9A'—C4A'	−0.6 (8)
C2—C1—C9A—C9	−178.2 (6)	C2'—C1'—C9A'—C9'	−179.2 (5)
O9—C9—C9A—C4A	−175.9 (5)	O9'—C9'—C9A'—C4A'	−178.5 (5)
C8A—C9—C9A—C4A	3.3 (8)	C8A'—C9'—C9A'—C4A'	2.7 (7)
O9—C9—C9A—C1	5.0 (9)	O9'—C9'—C9A'—C1'	0.0 (7)
C8A—C9—C9A—C1	−175.9 (5)	C8A'—C9'—C9A'—C1'	−178.8 (4)
C9A—C4A—C10—C10A	−1.9 (6)	C4'—C4A'—C10'—C11'	−52.4 (5)
C4—C4A—C10—C10A	179.8 (4)	C9A'—C4A'—C10'—C11'	128.2 (4)
C9A—C4A—C10—C11	−130.2 (4)	C4'—C4A'—C10'—C10A'	178.5 (4)
C4—C4A—C10—C11	51.4 (5)	C9A'—C4A'—C10'—C10A'	−0.9 (6)
C9A—C4A—C10—N	113.4 (4)	C4'—C4A'—C10'—N'	63.8 (5)
C4—C4A—C10—N	−64.9 (5)	C9A'—C4A'—C10'—N'	−115.6 (4)
O1—N—C10—C4A	−56.6 (5)	O1'—N'—C10'—C11'	−164.3 (4)
O2—N—C10—C4A	121.6 (5)	O2'—N'—C10'—C11'	21.6 (5)
O1—N—C10—C10A	65.4 (5)	O1'—N'—C10'—C10A'	−45.1 (5)
O2—N—C10—C10A	−116.4 (6)	O2'—N'—C10'—C10A'	140.8 (4)
O1—N—C10—C11	−175.4 (4)	O1'—N'—C10'—C4A'	76.7 (5)
O2—N—C10—C11	2.8 (7)	O2'—N'—C10'—C4A'	−97.4 (5)
C6—C5—C10A—C8A	−1.1 (7)	C6'—C5'—C10A'—C8A'	−1.5 (7)
C6—C5—C10A—C10	179.2 (5)	C6'—C5'—C10A'—C10'	−179.3 (4)
C8—C8A—C10A—C5	1.1 (7)	C8'—C8A'—C10A'—C5'	0.9 (7)
C9—C8A—C10A—C5	−178.0 (5)	C9'—C8A'—C10A'—C5'	179.8 (4)
C8—C8A—C10A—C10	−179.3 (4)	C8'—C8A'—C10A'—C10'	178.6 (4)
C9—C8A—C10A—C10	1.6 (7)	C9'—C8A'—C10A'—C10'	−2.4 (6)
C4A—C10—C10A—C5	−179.2 (4)	C11'—C10'—C10A'—C5'	51.6 (5)
C11—C10—C10A—C5	−51.1 (5)	C4A'—C10'—C10A'—C5'	−179.2 (4)
N—C10—C10A—C5	65.2 (5)	N'—C10'—C10A'—C5'	−65.2 (5)
C4A—C10—C10A—C8A	1.2 (6)	C11'—C10'—C10A'—C8A'	−126.2 (4)
C11—C10—C10A—C8A	129.3 (4)	C4A'—C10'—C10A'—C8A'	3.1 (6)
N—C10—C10A—C8A	−114.4 (5)	N'—C10'—C10A'—C8A'	117.1 (4)
C4A—C10—C11—C12	63.0 (5)	C11—C12—C11'—C10'	178.4 (4)
C10A—C10—C11—C12	−67.1 (5)	C10A'—C10'—C11'—C12	63.3 (5)
N—C10—C11—C12	178.1 (4)	C4A'—C10'—C11'—C12	−67.8 (5)
C10—C11—C12—C11'	179.1 (4)	N'—C10'—C11'—C12	178.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2′—H2′···O2^i	0.93	2.67	3.586 (10)	168
C4—H4···O9^ii	0.93	2.60	3.417 (6)	147
C5—H5···O2′^iii	0.93	2.69	3.363 (7)	130
C5′—H5′···O2^iii	0.93	2.53	3.343 (7)	146
C7′—H7′···O2′^iv	0.93	2.57	3.473 (7)	165

Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) x−1/2, −y+3/2, z−1/2; (iii) −x+1, −y+1, −z+3; (iv) x+1/2, −y+1/2, z+1/2.