6-Amino-4-(3-nitro­phen­yl)-2-oxo-1,2-dihydro­pyridine-3,5-dicarbonitrile ethanol solvate

The title compound, C₁₃H₇N₅O₃·C₂H₆O, was synthesized by the reaction of 2-cyano­acetamide, malononitrile and 3-nitro­benzaldehyde in water. The asymmetric unit contains two crystallographically independent 6-amino-4-(3-nitro­phen­yl)-2-oxo-1,2-dihydro­pyridine-3,5-dicarbonitrile mol­ecules of similar conformation and two ethanol solvent mol­ecules. The nitro group of one mol­ecule is disordered over two positions with site-occupation factors of 0.688 (17) and 0.312 (17). The dihedral angles between the pyridine and benzene rings are 52.06 (11) and 65.12 (13)° in the two mol­ecules. The crystal packing is stabilized by N—H...O, N—H...N, O—H...O and C—H...O intra- and inter­molecular hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in main residue
• R factor = 0.058
• wR factor = 0.124
• Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         34 Perc.

Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       N10'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N5
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        C29
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.06
PLAT301_ALERT_3_C Main Residue  Disorder .........................       7.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C22    -   C23    ...       1.37 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C23    -   C24    ...       1.36 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C15    -   C19    ...       1.42 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C17    -   C20    ...       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C2     -   C6     ...       1.42 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C4     -   C7     ...       1.42 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O6'    ..  C1      ..       2.99 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C1     ..  O6      ..       2.95 Ang.

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......        160

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

The synthesis of 2-pyridone derivatives is an area of growing interest because compounds with these scaffolds exhibited significant pharmacological properties such as antibacterial (Li et al., 2000), antifungal (Cox & O'Hagan, 1991) and antitumor activity (Nagarajan et al., 2003). These compounds have been used also as cardiotonic (Deshang et al., 1988) and psychotherapeutic agents (Kozikowski et al., 1996) and potential HIC-1 specific transcriptase inhibitors (Boeckman et al., 1987). Moreover it is well know that the 2-pyridone ring system is a valuable building block in the symthesis of natural products (Comins et al., 1994). For these reasons, the synthesis of new compounds containing 2-pyridone derivatives is strongly desired. In this paper we report the crystal structure of the title compound.

In the asymmetric units there are two title molecules of similar geometry and two ethanol molecules (Fig. 1). One nitro group is disordered over two positions, with refined site occupation factors of 0.688 (17) and 0.312 (17) for the major and minor components, respectively. The dihedral angle between the C1/C2/C3/C4/C5/N1 plane and the C8—C13 benzene ring is 52.06 (11) °, while the corresponding angle between the C14/C15/C16/C17/C18/N6 plane and the C21—C26 benzene ring is 65.12 (13)°. The crystal packing is stabilized by an extended network of N—H···O, N—H···N, O—H···O and C—H···O intra- and intermolecular hydrogen bonds (Table 1, Fig. 2).

Related literature

For general background, see: Boeckman et al. (1987); Comins et al. (1994); Cox & O'Hagan (1991); Deshang et al. (1988); Kozikowski et al. (1996); Li et al. (2000); Nagarajan et al. (2003).

S2. Experimental

The title Compound was prepared by the reaction of 2-cyanoacetamide (2 mmol), malononitrile (2 mmol) and 3-nitrobenzaldehyde (2 mmol) in water (2 ml). Single crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a 95% aqueous ethanol solution (yield 48%; m.p. >573 K). IR (cm^-1): 3546, 3338, 3189, 2214, 1670, 1646, 1529; ¹H NMR (DMSO-d₆): 7.87 (2H, brs, NH₂), 7.88–8.01 (4H, m, ArH), 11.85 (1H, s, NH).

S3. Refinement

All H atoms were positioned geometrically and treated as riding, with N—H = 0.86 Å, O—H = 0.82 Å and C—H = 0.93–0.97 Å, and with U_iso(H) = 1.2 U_eq(C, N) or 1.5 U_eq(C, O) for methyl and hydroxy groups.

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound viewed along the b axis. Dashed lines indicate hydrogen bonds.

6-Amino-4-(3-nitrophenyl)-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile ethanol solvate

Crystal data

C13H7N5O3·C2H6O	F(000) = 1360
Mr = 327.30	Dx = 1.349 Mg m^−3
Monoclinic, P21/n	Melting point > 573 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 13.079 (3) Å	Cell parameters from 1628 reflections
b = 14.764 (4) Å	θ = 2.4–19,693°
c = 16.693 (4) Å	µ = 0.10 mm^−1
β = 90.923 (4)°	T = 298 K
V = 3223.0 (14) Å^3	Block, yellow
Z = 8	0.45 × 0.36 × 0.31 mm

Data collection

Bruker SMART CCD area-detector diffractometer	5690 independent reflections
Radiation source: fine-focus sealed tube	1952 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.089
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.950, Tmax = 0.962	k = −15→17
16780 measured reflections	l = −19→16

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.124	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0257P)^2] where P = (Fo^2 + 2Fc^2)/3
5690 reflections	(Δ/σ)max < 0.001
465 parameters	Δρmax = 0.38 e Å^−3
160 restraints	Δρmin = −0.33 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.

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	Occ. (<1)
N1	0.5413 (2)	−0.0007 (2)	0.88884 (17)	0.0437 (9)
H1	0.5749	−0.0469	0.9064	0.052*
N2	0.6368 (3)	0.2644 (3)	0.7473 (2)	0.0869 (14)
N3	0.1889 (3)	0.0708 (2)	0.8869 (2)	0.0649 (11)
N4	0.3967 (2)	−0.0744 (2)	0.92758 (17)	0.0535 (10)
H4A	0.4351	−0.1178	0.9448	0.064*
H4B	0.3315	−0.0780	0.9321	0.064*
N5	0.3662 (4)	0.4712 (3)	0.8369 (3)	0.0937 (16)
N6	0.6783 (2)	0.4244 (2)	0.59015 (17)	0.0485 (9)
H6	0.7123	0.4700	0.6084	0.058*
N7	0.7718 (3)	0.1339 (3)	0.4923 (2)	0.0779 (13)
N8	0.3234 (3)	0.3745 (2)	0.5484 (2)	0.0711 (12)
N9	0.5327 (2)	0.5071 (2)	0.61243 (18)	0.0612 (10)
H9A	0.5706	0.5513	0.6288	0.073*
H9B	0.4673	0.5127	0.6117	0.073*
N10	0.447 (3)	0.099 (3)	0.305 (2)	0.107 (9)	0.312 (17)
N10'	0.4599 (12)	0.0567 (11)	0.3306 (8)	0.098 (4)	0.688 (17)
O1	0.69115 (19)	0.06659 (18)	0.85852 (15)	0.0582 (8)
O2	0.4461 (4)	0.4791 (3)	0.8736 (3)	0.1390 (18)
O3	0.3055 (3)	0.5318 (3)	0.8276 (2)	0.1389 (18)
O4	0.82853 (19)	0.35442 (18)	0.56654 (15)	0.0615 (9)
O5	0.4957 (16)	0.1407 (14)	0.2640 (11)	0.097 (6)	0.312 (17)
O6	0.3707 (16)	0.0454 (18)	0.2843 (11)	0.128 (7)	0.312 (17)
O5'	0.5210 (8)	0.0869 (12)	0.2864 (7)	0.136 (4)	0.688 (17)
O6'	0.4135 (8)	−0.0099 (8)	0.3139 (6)	0.137 (4)	0.688 (17)
O7	0.0021 (2)	0.2717 (2)	0.5108 (2)	0.0806 (10)
H7	−0.0559	0.2762	0.5283	0.121*
O8	0.6269 (2)	0.6604 (3)	0.6769 (2)	0.1075 (13)
H8	0.6889	0.6636	0.6709	0.161*
C1	0.5962 (3)	0.0702 (3)	0.8570 (2)	0.0447 (11)
C2	0.5381 (3)	0.1436 (3)	0.8234 (2)	0.0431 (11)
C3	0.4334 (3)	0.1448 (3)	0.8294 (2)	0.0408 (10)
C4	0.3825 (3)	0.0726 (3)	0.8654 (2)	0.0400 (10)
C5	0.4381 (3)	−0.0024 (3)	0.8943 (2)	0.0406 (11)
C6	0.5925 (3)	0.2113 (3)	0.7813 (3)	0.0572 (13)
C7	0.2748 (3)	0.0719 (3)	0.8769 (2)	0.0459 (11)
C8	0.3733 (3)	0.2238 (3)	0.8012 (2)	0.0466 (11)
C9	0.3988 (3)	0.3087 (3)	0.8279 (2)	0.0544 (12)
H9	0.4558	0.3170	0.8612	0.065*
C10	0.3397 (4)	0.3813 (3)	0.8054 (3)	0.0634 (14)
C11	0.2560 (4)	0.3732 (4)	0.7573 (3)	0.0808 (17)
H11	0.2168	0.4236	0.7438	0.097*
C12	0.2302 (4)	0.2888 (4)	0.7289 (3)	0.0791 (16)
H12	0.1734	0.2818	0.6953	0.095*
C13	0.2886 (3)	0.2144 (3)	0.7503 (2)	0.0628 (13)
H13	0.2711	0.1575	0.7305	0.075*
C14	0.7335 (3)	0.3502 (3)	0.5651 (2)	0.0453 (11)
C15	0.6741 (3)	0.2752 (3)	0.5383 (2)	0.0445 (11)
C16	0.5687 (3)	0.2784 (3)	0.5358 (2)	0.0424 (11)
C17	0.5190 (3)	0.3557 (3)	0.5605 (2)	0.0430 (11)
C18	0.5750 (3)	0.4312 (3)	0.5884 (2)	0.0449 (11)
C19	0.7282 (3)	0.1969 (3)	0.5126 (3)	0.0547 (13)
C20	0.4105 (3)	0.3644 (3)	0.5539 (2)	0.0507 (12)
C21	0.5069 (3)	0.1995 (3)	0.5085 (3)	0.0462 (11)
C22	0.5108 (3)	0.1706 (3)	0.4295 (3)	0.0638 (14)
H22	0.5532	0.1988	0.3929	0.077*
C23	0.4500 (4)	0.0988 (4)	0.4074 (3)	0.0753 (16)
C24	0.3867 (4)	0.0549 (3)	0.4580 (4)	0.0872 (19)
H24	0.3459	0.0073	0.4398	0.105*
C25	0.3839 (3)	0.0819 (3)	0.5366 (4)	0.0821 (16)
H25	0.3425	0.0523	0.5730	0.098*
C26	0.4444 (3)	0.1545 (3)	0.5604 (3)	0.0621 (13)
H26	0.4426	0.1733	0.6136	0.074*
C27	0.0420 (4)	0.1856 (4)	0.5300 (3)	0.0975 (18)
H27A	−0.0073	0.1394	0.5149	0.117*
H27B	0.0540	0.1816	0.5874	0.117*
C28	0.1378 (4)	0.1693 (4)	0.4885 (3)	0.140 (2)
H28A	0.1244	0.1647	0.4320	0.210*
H28B	0.1679	0.1139	0.5076	0.210*
H28C	0.1841	0.2186	0.4988	0.210*
C29	0.6040 (6)	0.6753 (5)	0.7591 (5)	0.180 (4)
H29A	0.5308	0.6793	0.7670	0.216*
H29B	0.6364	0.7300	0.7792	0.216*
C30	0.6487 (6)	0.5913 (5)	0.7994 (5)	0.210 (4)
H30A	0.6229	0.5381	0.7729	0.315*
H30B	0.6295	0.5902	0.8546	0.315*
H30C	0.7219	0.5927	0.7960	0.315*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.035 (2)	0.043 (2)	0.053 (2)	0.0012 (18)	−0.0031 (17)	0.0028 (17)
N2	0.075 (3)	0.077 (4)	0.109 (4)	−0.005 (3)	0.027 (3)	0.023 (3)
N3	0.038 (2)	0.068 (3)	0.088 (3)	0.005 (2)	0.008 (2)	0.008 (2)
N4	0.0299 (19)	0.057 (3)	0.074 (3)	0.0025 (19)	−0.0017 (18)	0.007 (2)
N5	0.120 (5)	0.046 (4)	0.116 (4)	0.016 (4)	0.017 (4)	0.005 (3)
N6	0.032 (2)	0.050 (3)	0.063 (2)	−0.0055 (19)	−0.0007 (18)	−0.0132 (19)
N7	0.061 (3)	0.071 (3)	0.101 (3)	0.006 (2)	0.012 (2)	−0.017 (3)
N8	0.036 (2)	0.072 (3)	0.105 (3)	0.001 (2)	0.008 (2)	−0.022 (2)
N9	0.035 (2)	0.058 (3)	0.092 (3)	0.0023 (19)	0.0032 (19)	−0.019 (2)
N10	0.105 (12)	0.112 (12)	0.105 (12)	−0.017 (9)	0.001 (9)	−0.032 (9)
N10'	0.083 (7)	0.116 (11)	0.095 (9)	−0.039 (7)	0.000 (7)	−0.048 (7)
O1	0.0329 (17)	0.062 (2)	0.080 (2)	−0.0014 (15)	0.0019 (15)	0.0115 (15)
O2	0.133 (4)	0.062 (3)	0.221 (5)	−0.007 (3)	−0.013 (4)	−0.019 (3)
O3	0.213 (5)	0.066 (3)	0.137 (4)	0.069 (3)	0.002 (3)	0.007 (2)
O4	0.0309 (17)	0.060 (2)	0.094 (2)	−0.0044 (15)	−0.0003 (16)	−0.0134 (16)
O5	0.100 (9)	0.111 (9)	0.081 (8)	−0.026 (7)	0.011 (7)	−0.023 (7)
O6	0.124 (9)	0.142 (10)	0.119 (9)	−0.041 (8)	−0.006 (7)	−0.048 (7)
O5'	0.121 (6)	0.177 (8)	0.111 (6)	−0.032 (6)	0.028 (5)	−0.068 (6)
O6'	0.152 (6)	0.122 (7)	0.137 (6)	−0.020 (5)	−0.022 (5)	−0.061 (5)
O7	0.056 (2)	0.070 (2)	0.116 (3)	−0.0024 (19)	0.009 (2)	−0.014 (2)
O8	0.067 (2)	0.105 (3)	0.151 (4)	−0.005 (2)	0.003 (2)	−0.043 (3)
C1	0.033 (3)	0.053 (3)	0.048 (3)	−0.006 (3)	0.005 (2)	−0.006 (2)
C2	0.039 (3)	0.040 (3)	0.050 (3)	0.004 (2)	0.003 (2)	0.003 (2)
C3	0.041 (3)	0.038 (3)	0.043 (3)	0.001 (2)	0.002 (2)	−0.006 (2)
C4	0.030 (2)	0.040 (3)	0.050 (3)	0.001 (2)	−0.001 (2)	−0.004 (2)
C5	0.032 (3)	0.044 (3)	0.047 (3)	−0.007 (2)	0.004 (2)	−0.005 (2)
C6	0.041 (3)	0.051 (4)	0.080 (4)	0.004 (2)	0.011 (3)	0.006 (3)
C7	0.042 (3)	0.041 (3)	0.055 (3)	0.004 (2)	0.002 (2)	0.000 (2)
C8	0.043 (3)	0.043 (3)	0.054 (3)	0.002 (2)	0.004 (2)	0.001 (2)
C9	0.045 (3)	0.049 (3)	0.069 (3)	0.007 (3)	0.006 (2)	0.003 (3)
C10	0.064 (4)	0.051 (4)	0.076 (4)	0.011 (3)	0.012 (3)	0.007 (3)
C11	0.074 (4)	0.075 (5)	0.094 (4)	0.028 (4)	0.018 (3)	0.034 (3)
C12	0.061 (3)	0.088 (5)	0.088 (4)	0.009 (4)	−0.017 (3)	0.026 (4)
C13	0.056 (3)	0.067 (4)	0.064 (3)	0.001 (3)	−0.004 (3)	0.002 (3)
C14	0.034 (3)	0.053 (3)	0.049 (3)	0.001 (2)	0.004 (2)	−0.008 (2)
C15	0.034 (3)	0.047 (3)	0.053 (3)	0.000 (2)	0.003 (2)	−0.010 (2)
C16	0.034 (3)	0.047 (3)	0.046 (3)	−0.005 (2)	0.001 (2)	−0.006 (2)
C17	0.027 (2)	0.052 (3)	0.050 (3)	−0.004 (2)	0.002 (2)	−0.008 (2)
C18	0.029 (3)	0.049 (3)	0.056 (3)	0.002 (2)	0.003 (2)	−0.006 (2)
C19	0.038 (3)	0.063 (4)	0.063 (3)	−0.010 (3)	0.006 (2)	−0.006 (3)
C20	0.047 (3)	0.043 (3)	0.062 (3)	−0.003 (3)	0.005 (3)	−0.012 (2)
C21	0.036 (3)	0.049 (3)	0.053 (3)	−0.002 (2)	0.004 (2)	−0.010 (3)
C22	0.041 (3)	0.080 (4)	0.071 (4)	−0.018 (3)	0.006 (2)	−0.023 (3)
C23	0.051 (3)	0.089 (4)	0.087 (4)	−0.010 (3)	0.008 (3)	−0.050 (4)
C24	0.053 (4)	0.068 (4)	0.142 (6)	−0.016 (3)	0.014 (4)	−0.037 (4)
C25	0.057 (3)	0.067 (4)	0.122 (5)	−0.015 (3)	0.016 (3)	−0.004 (4)
C26	0.049 (3)	0.070 (4)	0.067 (3)	−0.009 (3)	0.016 (3)	−0.007 (3)
C27	0.100 (5)	0.090 (5)	0.102 (5)	0.010 (4)	−0.007 (4)	0.009 (3)
C28	0.079 (4)	0.175 (7)	0.166 (6)	0.048 (4)	0.017 (4)	0.008 (5)
C29	0.155 (7)	0.210 (10)	0.177 (8)	0.007 (7)	0.016 (6)	−0.073 (7)
C30	0.175 (7)	0.281 (8)	0.175 (7)	−0.054 (6)	0.038 (5)	−0.045 (6)

Geometric parameters (Å, º)

N1—C5	1.355 (4)	C8—C13	1.392 (5)
N1—C1	1.380 (4)	C9—C10	1.370 (5)
N1—H1	0.8600	C9—H9	0.9300
N2—C6	1.132 (5)	C10—C11	1.352 (6)
N3—C7	1.139 (4)	C11—C12	1.373 (6)
N4—C5	1.320 (4)	C11—H11	0.9300
N4—H4A	0.8600	C12—C13	1.382 (6)
N4—H4B	0.8600	C12—H12	0.9300
N5—O3	1.205 (5)	C13—H13	0.9300
N5—O2	1.210 (5)	C14—C15	1.421 (5)
N5—C10	1.466 (6)	C15—C16	1.380 (5)
N6—C18	1.354 (4)	C15—C19	1.426 (5)
N6—C14	1.380 (4)	C16—C17	1.379 (5)
N6—H6	0.8600	C16—C21	1.485 (5)
N7—C19	1.145 (5)	C17—C18	1.409 (5)
N8—C20	1.151 (4)	C17—C20	1.427 (5)
N9—C18	1.316 (4)	C21—C26	1.374 (5)
N9—H9A	0.8600	C21—C22	1.386 (5)
N9—H9B	0.8600	C22—C23	1.373 (5)
N10—O5	1.13 (4)	C22—H22	0.9300
N10—O6	1.32 (4)	C23—C24	1.357 (6)
N10—C23	1.70 (4)	C24—C25	1.373 (6)
N10'—O5'	1.183 (13)	C24—H24	0.9300
N10'—O6'	1.186 (11)	C25—C26	1.386 (5)
N10'—C23	1.433 (13)	C25—H25	0.9300
O1—C1	1.242 (4)	C26—H26	0.9300
O4—C14	1.245 (4)	C27—C28	1.460 (6)
O7—C27	1.410 (5)	C27—H27A	0.9700
O7—H7	0.8200	C27—H27B	0.9700
O8—C29	1.427 (7)	C28—H28A	0.9600
O8—H8	0.8200	C28—H28B	0.9600
C1—C2	1.433 (5)	C28—H28C	0.9600
C2—C3	1.374 (5)	C29—C30	1.523 (8)
C2—C6	1.420 (5)	C29—H29A	0.9700
C3—C4	1.396 (5)	C29—H29B	0.9700
C3—C8	1.480 (5)	C30—H30A	0.9600
C4—C5	1.406 (5)	C30—H30B	0.9600
C4—C7	1.425 (5)	C30—H30C	0.9600
C8—C9	1.370 (5)
C5—N1—C1	124.4 (4)	N6—C14—C15	115.3 (4)
C5—N1—H1	117.8	C16—C15—C14	121.6 (4)
C1—N1—H1	117.8	C16—C15—C19	121.3 (4)
C5—N4—H4A	120.0	C14—C15—C19	117.1 (4)
C5—N4—H4B	120.0	C17—C16—C15	119.7 (4)
H4A—N4—H4B	120.0	C17—C16—C21	118.9 (4)
O3—N5—O2	123.7 (6)	C15—C16—C21	121.4 (4)
O3—N5—C10	118.4 (6)	C16—C17—C18	120.5 (4)
O2—N5—C10	117.8 (6)	C16—C17—C20	121.6 (4)
C18—N6—C14	125.3 (4)	C18—C17—C20	117.7 (4)
C18—N6—H6	117.3	N9—C18—N6	118.7 (4)
C14—N6—H6	117.3	N9—C18—C17	123.7 (4)
C18—N9—H9A	120.0	N6—C18—C17	117.5 (4)
C18—N9—H9B	120.0	N7—C19—C15	179.7 (6)
H9A—N9—H9B	120.0	N8—C20—C17	177.8 (5)
O5—N10—O6	127 (3)	C26—C21—C22	118.8 (4)
O5—N10—C23	128 (3)	C26—C21—C16	120.8 (4)
O6—N10—C23	106 (3)	C22—C21—C16	120.3 (4)
O5'—N10'—O6'	121.0 (13)	C23—C22—C21	117.6 (4)
O5'—N10'—C23	117.8 (11)	C23—C22—H22	121.2
O6'—N10'—C23	121.1 (12)	C21—C22—H22	121.2
C27—O7—H7	109.5	C24—C23—C22	123.9 (5)
C29—O8—H8	109.5	C24—C23—N10'	114.5 (8)
O1—C1—N1	119.1 (4)	C22—C23—N10'	121.0 (7)
O1—C1—C2	124.3 (4)	C24—C23—N10	128.3 (15)
N1—C1—C2	116.6 (4)	C22—C23—N10	105.7 (14)
C3—C2—C6	122.4 (4)	C23—C24—C25	118.8 (5)
C3—C2—C1	120.3 (4)	C23—C24—H24	120.6
C6—C2—C1	117.3 (4)	C25—C24—H24	120.6
C2—C3—C4	120.3 (4)	C24—C25—C26	118.4 (5)
C2—C3—C8	120.8 (4)	C24—C25—H25	120.8
C4—C3—C8	118.9 (4)	C26—C25—H25	120.8
C3—C4—C5	120.1 (4)	C21—C26—C25	122.4 (5)
C3—C4—C7	122.9 (4)	C21—C26—H26	118.8
C5—C4—C7	117.0 (4)	C25—C26—H26	118.8
N4—C5—N1	117.3 (4)	O7—C27—C28	111.0 (5)
N4—C5—C4	124.5 (4)	O7—C27—H27A	109.4
N1—C5—C4	118.2 (4)	C28—C27—H27A	109.4
N2—C6—C2	179.0 (6)	O7—C27—H27B	109.4
N3—C7—C4	179.3 (5)	C28—C27—H27B	109.4
C9—C8—C13	118.5 (4)	H27A—C27—H27B	108.0
C9—C8—C3	119.5 (4)	C27—C28—H28A	109.5
C13—C8—C3	122.0 (4)	C27—C28—H28B	109.5
C10—C9—C8	119.5 (4)	H28A—C28—H28B	109.5
C10—C9—H9	120.2	C27—C28—H28C	109.5
C8—C9—H9	120.2	H28A—C28—H28C	109.5
C11—C10—C9	122.8 (5)	H28B—C28—H28C	109.5
C11—C10—N5	118.5 (5)	O8—C29—C30	102.3 (6)
C9—C10—N5	118.7 (5)	O8—C29—H29A	111.3
C10—C11—C12	118.5 (5)	C30—C29—H29A	111.3
C10—C11—H11	120.7	O8—C29—H29B	111.3
C12—C11—H11	120.7	C30—C29—H29B	111.3
C11—C12—C13	120.0 (5)	H29A—C29—H29B	109.2
C11—C12—H12	120.0	C29—C30—H30A	109.5
C13—C12—H12	120.0	C29—C30—H30B	109.5
C12—C13—C8	120.7 (5)	H30A—C30—H30B	109.5
C12—C13—H13	119.7	C29—C30—H30C	109.5
C8—C13—H13	119.7	H30A—C30—H30C	109.5
O4—C14—N6	118.8 (4)	H30B—C30—H30C	109.5
O4—C14—C15	125.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9A···O8	0.86	1.94	2.785 (5)	167
C22—H22···O5	0.93	2.42	2.802 (19)	104
N1—H1···O4^i	0.86	1.98	2.826 (4)	170
N4—H4A···O7^ii	0.86	1.97	2.816 (4)	169
N4—H4B···N8^ii	0.86	2.17	3.009 (5)	164
C13—H13···O3^ii	0.93	2.32	3.228 (6)	167
C25—H25···O3^ii	0.93	2.59	3.464 (7)	158
N6—H6···O1^iii	0.86	1.98	2.830 (4)	171
O8—H8···O1^iii	0.82	2.19	2.824 (4)	135
N9—H9B···N3^iv	0.86	2.22	3.047 (5)	163
O7—H7···O4^v	0.82	2.01	2.753 (4)	150

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