4-Nitro-benzoic acid-N-(pyrimidin-2-yl)aniline (1/1).

Four independent mol-ecules comprise the asymmetric unit of the title co-crystal, C(10)H(9)N(3)·C(7)H(5)NO(4), two for each component. Small conformational differences are noted for the benzoic acid derivatives, notably in the twists of the carb-oxy-lic acid residue out of the plane of the benzene ring to which it is connected [torsion angles = 167.62 (17) and 174.54 (17)°]. In the aniline derivative, the major difference is observed in the dihedral angles formed between the CN(3) and phenyl least-squares planes [1.51 (5) and 6.25 (6)°]. Pairs of mol-ecules associate via O-H⋯N and N-H⋯O hydrogen bonds leading to eight-membered {⋯HOCO⋯HNCN} hetero-synthons. The two-mol-ecule aggregates are consolidated in the crystal structure by C-H⋯O(nitro) and π-π inter-actions [shortest centroid-centroid distance between benzene rings = 3.6242 (10) Å].

Related literature

For related studies in co-crystal formation, see: Wardell & Tiekink (2011 ▶). For the structure of N-(pyrimidin-2-yl)aniline, see: Badaruddin et al. (2009 ▶). For the structure of 4-nitro­benzoic acid, see: Tonogaki et al. (1993 ▶).

Experimental

Crystal data

C10H9N3·C7H5NO4

M = 338.32

Monoclinic,

a = 12.7754 (4) Å

b = 25.7788 (8) Å

c = 9.5813 (3) Å

β = 104.209 (4)°

V = 3058.92 (17) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.35 × 0.30 × 0.25 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.856, T max = 1.000

15808 measured reflections

6818 independent reflections

5093 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.118

S = 1.03

6818 reflections

463 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶), QMol (Gans & Shalloway, 2001 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811044175/ez2266sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044175/ez2266Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811044175/ez2266Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H9N3·C7H5NO4	F(000) = 1408
Mr = 338.32	Dx = 1.469 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5286 reflections
a = 12.7754 (4) Å	θ = 2.3–29.3°
b = 25.7788 (8) Å	µ = 0.11 mm−1
c = 9.5813 (3) Å	T = 100 K
β = 104.209 (4)°	Block, colourless
V = 3058.92 (17) Å3	0.35 × 0.30 × 0.25 mm
Z = 8

Agilent SuperNova Dual diffractometer with an Atlas detector	6818 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	5093 reflections with I > 2σ(I)
Mirror	Rint = 0.031
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.3°
ω scan	h = −16→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −25→33
Tmin = 0.856, Tmax = 1.000	l = −12→11
15808 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0435P)2 + 1.2445P] where P = (Fo2 + 2Fc2)/3
6818 reflections	(Δ/σ)max < 0.001
463 parameters	Δρmax = 0.26 e Å−3
4 restraints	Δρmin = −0.28 e Å−3

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

	x	y	z	Uiso*/Ueq
O1	0.85371 (10)	0.60855 (5)	0.50402 (13)	0.0228 (3)
O2	0.73858 (10)	0.55038 (5)	0.55581 (14)	0.0244 (3)
H2O	0.7228 (17)	0.5752 (6)	0.608 (2)	0.037*
O3	1.04527 (12)	0.41493 (6)	0.13302 (18)	0.0414 (4)
O4	0.95094 (12)	0.35836 (5)	0.21412 (17)	0.0382 (4)
O5	0.60266 (10)	0.23665 (5)	0.43762 (14)	0.0236 (3)
O6	0.67258 (11)	0.29895 (5)	0.32451 (14)	0.0264 (3)
H6O	0.7045 (17)	0.2740 (6)	0.294 (2)	0.040*
O7	0.39904 (11)	0.43347 (5)	0.78791 (14)	0.0292 (3)
O8	0.48451 (11)	0.49026 (5)	0.69235 (14)	0.0268 (3)
N1	0.75301 (12)	0.69124 (6)	0.65279 (16)	0.0184 (3)
H1N	0.7837 (14)	0.6684 (6)	0.6080 (19)	0.022*
N2	0.67877 (11)	0.61741 (5)	0.71728 (15)	0.0179 (3)
N3	0.63472 (12)	0.69905 (5)	0.80552 (15)	0.0182 (3)
N4	0.74841 (12)	0.15764 (6)	0.34898 (16)	0.0206 (3)
H4N	0.7060 (13)	0.1808 (6)	0.375 (2)	0.025*
N5	0.78776 (12)	0.22892 (6)	0.23078 (16)	0.0195 (3)
N6	0.87374 (12)	0.14807 (6)	0.20705 (16)	0.0208 (3)
N7	0.97993 (13)	0.40311 (6)	0.20136 (18)	0.0272 (4)
N8	0.45857 (12)	0.44542 (6)	0.71057 (15)	0.0196 (3)
C1	0.68704 (14)	0.66985 (7)	0.72861 (18)	0.0168 (4)
C2	0.62103 (14)	0.59339 (7)	0.79624 (19)	0.0201 (4)
H2	0.6140	0.5567	0.7900	0.024*
C3	0.57137 (14)	0.61991 (7)	0.88640 (19)	0.0206 (4)
H3	0.5336	0.6025	0.9466	0.025*
C4	0.57942 (14)	0.67334 (7)	0.88454 (18)	0.0191 (4)
H4	0.5435	0.6928	0.9429	0.023*
C5	0.78214 (14)	0.74334 (7)	0.63821 (18)	0.0173 (4)
C6	0.85205 (14)	0.75203 (7)	0.54896 (19)	0.0191 (4)
H6	0.8780	0.7234	0.5047	0.023*
C7	0.88375 (14)	0.80179 (7)	0.52446 (19)	0.0213 (4)
H7	0.9305	0.8072	0.4625	0.026*
C8	0.84778 (15)	0.84381 (7)	0.58981 (19)	0.0212 (4)
H8	0.8695	0.8780	0.5731	0.025*
C9	0.77973 (15)	0.83529 (7)	0.67983 (19)	0.0214 (4)
H9	0.7554	0.8640	0.7257	0.026*
C10	0.74631 (15)	0.78552 (7)	0.70434 (19)	0.0202 (4)
H10	0.6992	0.7803	0.7660	0.024*
C11	0.80609 (14)	0.17769 (7)	0.25915 (18)	0.0183 (4)
C12	0.84094 (14)	0.25086 (7)	0.14286 (19)	0.0211 (4)
H12	0.8299	0.2867	0.1210	0.025*
C13	0.91108 (15)	0.22362 (7)	0.0826 (2)	0.0233 (4)
H13	0.9477	0.2395	0.0186	0.028*
C14	0.92555 (14)	0.17199 (7)	0.11999 (19)	0.0214 (4)
H14	0.9750	0.1524	0.0818	0.026*
C15	0.74319 (14)	0.10683 (7)	0.40058 (19)	0.0187 (4)
C16	0.68064 (15)	0.10025 (7)	0.50034 (19)	0.0222 (4)
H16	0.6465	0.1294	0.5308	0.027*
C17	0.66824 (15)	0.05151 (7)	0.5550 (2)	0.0233 (4)
H17	0.6251	0.0474	0.6222	0.028*
C18	0.71820 (15)	0.00886 (7)	0.51246 (19)	0.0228 (4)
H18	0.7098	−0.0246	0.5500	0.027*
C19	0.78049 (15)	0.01546 (7)	0.4146 (2)	0.0253 (4)
H19	0.8151	−0.0138	0.3854	0.030*
C20	0.79362 (15)	0.06385 (7)	0.3581 (2)	0.0228 (4)
H20	0.8368	0.0676	0.2909	0.027*
C28	0.61670 (14)	0.28223 (7)	0.41411 (18)	0.0192 (4)
C29	0.57437 (14)	0.32553 (7)	0.48937 (18)	0.0180 (4)
C30	0.59992 (14)	0.37699 (7)	0.46832 (19)	0.0196 (4)
H30	0.6429	0.3850	0.4032	0.023*
C31	0.56314 (14)	0.41665 (7)	0.54154 (19)	0.0196 (4)
H31	0.5808	0.4518	0.5282	0.023*
C32	0.50015 (14)	0.40359 (7)	0.63449 (18)	0.0177 (4)
C33	0.47428 (15)	0.35275 (7)	0.65914 (19)	0.0209 (4)
H33	0.4316	0.3449	0.7249	0.025*
C34	0.51214 (14)	0.31377 (7)	0.58564 (19)	0.0213 (4)
H34	0.4955	0.2786	0.6010	0.026*
C21	0.81529 (14)	0.56496 (7)	0.49520 (18)	0.0183 (4)
C22	0.85442 (14)	0.52222 (7)	0.41378 (18)	0.0183 (4)
C23	0.82458 (14)	0.47097 (7)	0.42781 (19)	0.0207 (4)
H23	0.7765	0.4629	0.4862	0.025*
C24	0.86457 (15)	0.43168 (7)	0.35713 (19)	0.0217 (4)
H24	0.8444	0.3966	0.3659	0.026*
C25	0.93451 (14)	0.44478 (7)	0.27357 (19)	0.0204 (4)
C26	0.96440 (15)	0.49535 (7)	0.2557 (2)	0.0227 (4)
H26	1.0115	0.5033	0.1958	0.027*
C27	0.92389 (14)	0.53422 (7)	0.32744 (19)	0.0198 (4)
H27	0.9437	0.5693	0.3175	0.024*

	U11	U22	U33	U12	U13	U23
O1	0.0274 (7)	0.0153 (7)	0.0280 (7)	−0.0011 (5)	0.0110 (6)	−0.0024 (5)
O2	0.0285 (7)	0.0200 (7)	0.0293 (7)	−0.0027 (6)	0.0161 (6)	−0.0074 (6)
O3	0.0402 (9)	0.0332 (9)	0.0613 (10)	−0.0049 (7)	0.0326 (8)	−0.0181 (8)
O4	0.0361 (9)	0.0197 (8)	0.0628 (10)	−0.0052 (6)	0.0197 (8)	−0.0163 (7)
O5	0.0260 (7)	0.0173 (7)	0.0293 (7)	0.0011 (5)	0.0105 (6)	−0.0013 (5)
O6	0.0329 (8)	0.0208 (7)	0.0309 (7)	0.0078 (6)	0.0181 (6)	0.0019 (6)
O7	0.0396 (8)	0.0246 (7)	0.0313 (7)	−0.0007 (6)	0.0238 (7)	−0.0013 (6)
O8	0.0359 (8)	0.0134 (7)	0.0336 (8)	−0.0042 (6)	0.0136 (6)	−0.0028 (6)
N1	0.0219 (8)	0.0140 (8)	0.0229 (8)	0.0011 (6)	0.0120 (7)	−0.0021 (6)
N2	0.0186 (7)	0.0150 (7)	0.0209 (7)	0.0002 (6)	0.0061 (6)	−0.0003 (6)
N3	0.0188 (8)	0.0173 (8)	0.0195 (7)	0.0015 (6)	0.0068 (6)	−0.0011 (6)
N4	0.0210 (8)	0.0176 (8)	0.0266 (8)	0.0034 (6)	0.0122 (7)	0.0006 (6)
N5	0.0206 (8)	0.0167 (8)	0.0217 (8)	−0.0009 (6)	0.0063 (6)	0.0000 (6)
N6	0.0184 (8)	0.0213 (8)	0.0246 (8)	0.0013 (6)	0.0087 (7)	0.0000 (6)
N7	0.0209 (8)	0.0244 (9)	0.0369 (10)	−0.0021 (7)	0.0082 (7)	−0.0117 (7)
N8	0.0230 (8)	0.0172 (8)	0.0191 (8)	−0.0007 (6)	0.0058 (7)	−0.0013 (6)
C1	0.0159 (8)	0.0175 (9)	0.0167 (8)	0.0007 (7)	0.0033 (7)	0.0007 (7)
C2	0.0191 (9)	0.0184 (9)	0.0227 (9)	−0.0005 (7)	0.0051 (8)	0.0009 (7)
C3	0.0206 (9)	0.0216 (9)	0.0211 (9)	−0.0002 (8)	0.0081 (8)	0.0028 (7)
C4	0.0191 (9)	0.0206 (9)	0.0189 (9)	0.0009 (7)	0.0072 (7)	−0.0002 (7)
C5	0.0177 (9)	0.0159 (9)	0.0180 (9)	−0.0004 (7)	0.0041 (7)	0.0006 (7)
C6	0.0195 (9)	0.0186 (9)	0.0207 (9)	0.0020 (7)	0.0076 (8)	−0.0001 (7)
C7	0.0195 (9)	0.0226 (10)	0.0234 (9)	−0.0009 (8)	0.0085 (8)	0.0024 (8)
C8	0.0219 (9)	0.0173 (9)	0.0232 (9)	−0.0030 (8)	0.0035 (8)	0.0019 (7)
C9	0.0261 (10)	0.0172 (9)	0.0211 (9)	0.0008 (8)	0.0061 (8)	−0.0024 (7)
C10	0.0226 (9)	0.0196 (9)	0.0199 (9)	0.0004 (8)	0.0083 (8)	0.0006 (7)
C11	0.0176 (9)	0.0188 (9)	0.0180 (9)	−0.0022 (7)	0.0034 (7)	−0.0015 (7)
C12	0.0201 (9)	0.0191 (9)	0.0237 (9)	−0.0036 (8)	0.0044 (8)	0.0000 (7)
C13	0.0205 (9)	0.0231 (10)	0.0279 (10)	−0.0032 (8)	0.0090 (8)	0.0015 (8)
C14	0.0179 (9)	0.0251 (10)	0.0226 (9)	−0.0014 (8)	0.0075 (8)	−0.0023 (8)
C15	0.0166 (9)	0.0190 (9)	0.0196 (9)	−0.0014 (7)	0.0030 (7)	0.0005 (7)
C16	0.0213 (9)	0.0232 (10)	0.0234 (9)	0.0026 (8)	0.0082 (8)	−0.0003 (8)
C17	0.0212 (9)	0.0274 (10)	0.0222 (9)	−0.0010 (8)	0.0074 (8)	0.0034 (8)
C18	0.0222 (10)	0.0213 (10)	0.0240 (9)	−0.0042 (8)	0.0038 (8)	0.0026 (8)
C19	0.0270 (10)	0.0205 (10)	0.0296 (10)	0.0003 (8)	0.0091 (9)	−0.0012 (8)
C20	0.0234 (10)	0.0222 (10)	0.0258 (10)	−0.0018 (8)	0.0115 (8)	−0.0006 (8)
C28	0.0182 (9)	0.0203 (10)	0.0188 (9)	0.0038 (7)	0.0037 (7)	0.0016 (7)
C29	0.0174 (9)	0.0180 (9)	0.0174 (8)	0.0012 (7)	0.0022 (7)	0.0005 (7)
C30	0.0182 (9)	0.0213 (9)	0.0201 (9)	0.0006 (7)	0.0064 (7)	0.0009 (7)
C31	0.0207 (9)	0.0157 (9)	0.0223 (9)	−0.0002 (7)	0.0053 (8)	0.0021 (7)
C32	0.0174 (9)	0.0176 (9)	0.0177 (8)	0.0015 (7)	0.0036 (7)	−0.0013 (7)
C33	0.0239 (10)	0.0189 (9)	0.0222 (9)	−0.0025 (8)	0.0101 (8)	0.0003 (7)
C34	0.0232 (9)	0.0159 (9)	0.0253 (9)	0.0000 (8)	0.0065 (8)	0.0015 (7)
C21	0.0183 (9)	0.0198 (9)	0.0163 (8)	0.0030 (7)	0.0034 (7)	0.0013 (7)
C22	0.0169 (9)	0.0177 (9)	0.0181 (8)	0.0021 (7)	0.0002 (7)	−0.0011 (7)
C23	0.0206 (9)	0.0198 (9)	0.0221 (9)	−0.0002 (8)	0.0059 (8)	−0.0007 (7)
C24	0.0211 (9)	0.0177 (9)	0.0250 (9)	0.0004 (8)	0.0034 (8)	−0.0013 (7)
C25	0.0171 (9)	0.0193 (9)	0.0238 (9)	0.0023 (7)	0.0027 (8)	−0.0069 (7)
C26	0.0192 (9)	0.0234 (10)	0.0270 (10)	−0.0031 (8)	0.0085 (8)	−0.0046 (8)
C27	0.0188 (9)	0.0165 (9)	0.0233 (9)	0.0003 (7)	0.0039 (7)	−0.0022 (7)

O1—C21	1.221 (2)	C9—H9	0.9500
O2—C21	1.311 (2)	C10—H10	0.9500
O2—H2O	0.866 (9)	C12—C13	1.372 (3)
O3—N7	1.219 (2)	C12—H12	0.9500
O4—N7	1.227 (2)	C13—C14	1.379 (3)
O5—C28	1.218 (2)	C13—H13	0.9500
O6—C28	1.317 (2)	C14—H14	0.9500
O6—H6O	0.853 (9)	C15—C20	1.392 (2)
O7—N8	1.2243 (18)	C15—C16	1.399 (2)
O8—N8	1.2267 (18)	C16—C17	1.385 (3)
N1—C1	1.357 (2)	C16—H16	0.9500
N1—C5	1.410 (2)	C17—C18	1.382 (3)
N1—H1N	0.876 (9)	C17—H17	0.9500
N2—C2	1.332 (2)	C18—C19	1.381 (2)
N2—C1	1.358 (2)	C18—H18	0.9500
N3—C4	1.332 (2)	C19—C20	1.386 (3)
N3—C1	1.341 (2)	C19—H19	0.9500
N4—C11	1.365 (2)	C20—H20	0.9500
N4—C15	1.407 (2)	C28—C29	1.500 (2)
N4—H4N	0.881 (9)	C29—C34	1.391 (2)
N5—C12	1.331 (2)	C29—C30	1.393 (2)
N5—C11	1.357 (2)	C30—C31	1.386 (2)
N6—C14	1.336 (2)	C30—H30	0.9500
N6—C11	1.338 (2)	C31—C32	1.380 (2)
N7—C25	1.472 (2)	C31—H31	0.9500
N8—C32	1.472 (2)	C32—C33	1.386 (2)
C2—C3	1.373 (2)	C33—C34	1.381 (2)
C2—H2	0.9500	C33—H33	0.9500
C3—C4	1.382 (2)	C34—H34	0.9500
C3—H3	0.9500	C21—C22	1.505 (2)
C4—H4	0.9500	C22—C27	1.389 (2)
C5—C10	1.391 (2)	C22—C23	1.391 (2)
C5—C6	1.398 (2)	C23—C24	1.384 (2)
C6—C7	1.382 (2)	C23—H23	0.9500
C6—H6	0.9500	C24—C25	1.380 (2)
C7—C8	1.385 (2)	C24—H24	0.9500
C7—H7	0.9500	C25—C26	1.381 (3)
C8—C9	1.384 (2)	C26—C27	1.385 (2)
C8—H8	0.9500	C26—H26	0.9500
C9—C10	1.390 (2)	C27—H27	0.9500
C21—O2—H2O	110.5 (14)	C20—C15—C16	119.11 (16)
C28—O6—H6O	111.2 (15)	C20—C15—N4	124.96 (15)
C1—N1—C5	130.82 (15)	C16—C15—N4	115.93 (15)
C1—N1—H1N	113.6 (12)	C17—C16—C15	120.40 (16)
C5—N1—H1N	115.5 (12)	C17—C16—H16	119.8
C2—N2—C1	117.41 (15)	C15—C16—H16	119.8
C4—N3—C1	116.00 (15)	C18—C17—C16	120.40 (16)
C11—N4—C15	130.81 (15)	C18—C17—H17	119.8
C11—N4—H4N	112.5 (13)	C16—C17—H17	119.8
C15—N4—H4N	116.6 (13)	C19—C18—C17	119.15 (17)
C12—N5—C11	116.77 (15)	C19—C18—H18	120.4
C14—N6—C11	115.72 (15)	C17—C18—H18	120.4
O3—N7—O4	123.48 (16)	C18—C19—C20	121.40 (17)
O3—N7—C25	118.09 (15)	C18—C19—H19	119.3
O4—N7—C25	118.42 (15)	C20—C19—H19	119.3
O7—N8—O8	123.56 (14)	C19—C20—C15	119.55 (16)
O7—N8—C32	117.95 (14)	C19—C20—H20	120.2
O8—N8—C32	118.48 (14)	C15—C20—H20	120.2
N3—C1—N1	121.65 (16)	O5—C28—O6	124.38 (16)
N3—C1—N2	124.28 (15)	O5—C28—C29	122.83 (15)
N1—C1—N2	114.06 (15)	O6—C28—C29	112.76 (15)
N2—C2—C3	122.12 (17)	C34—C29—C30	119.75 (16)
N2—C2—H2	118.9	C34—C29—C28	119.25 (15)
C3—C2—H2	118.9	C30—C29—C28	120.96 (15)
C2—C3—C4	116.16 (16)	C31—C30—C29	120.58 (16)
C2—C3—H3	121.9	C31—C30—H30	119.7
C4—C3—H3	121.9	C29—C30—H30	119.7
N3—C4—C3	123.71 (16)	C32—C31—C30	118.07 (16)
N3—C4—H4	118.1	C32—C31—H31	121.0
C3—C4—H4	118.1	C30—C31—H31	121.0
C10—C5—C6	118.98 (16)	C31—C32—C33	122.79 (16)
C10—C5—N1	125.10 (15)	C31—C32—N8	118.63 (15)
C6—C5—N1	115.92 (15)	C33—C32—N8	118.57 (14)
C7—C6—C5	120.68 (16)	C34—C33—C32	118.24 (16)
C7—C6—H6	119.7	C34—C33—H33	120.9
C5—C6—H6	119.7	C32—C33—H33	120.9
C6—C7—C8	120.36 (16)	C33—C34—C29	120.54 (16)
C6—C7—H7	119.8	C33—C34—H34	119.7
C8—C7—H7	119.8	C29—C34—H34	119.7
C9—C8—C7	119.11 (16)	O1—C21—O2	124.39 (16)
C9—C8—H8	120.4	O1—C21—C22	122.06 (15)
C7—C8—H8	120.4	O2—C21—C22	113.54 (15)
C8—C9—C10	121.17 (16)	C27—C22—C23	119.97 (16)
C8—C9—H9	119.4	C27—C22—C21	119.21 (16)
C10—C9—H9	119.4	C23—C22—C21	120.78 (15)
C9—C10—C5	119.69 (16)	C24—C23—C22	120.34 (16)
C9—C10—H10	120.2	C24—C23—H23	119.8
C5—C10—H10	120.2	C22—C23—H23	119.8
N6—C11—N5	125.17 (15)	C25—C24—C23	118.30 (17)
N6—C11—N4	121.16 (16)	C25—C24—H24	120.8
N5—C11—N4	113.68 (15)	C23—C24—H24	120.8
N5—C12—C13	122.43 (17)	C24—C25—C26	122.76 (16)
N5—C12—H12	118.8	C24—C25—N7	118.70 (16)
C13—C12—H12	118.8	C26—C25—N7	118.54 (16)
C12—C13—C14	116.37 (16)	C25—C26—C27	118.24 (16)
C12—C13—H13	121.8	C25—C26—H26	120.9
C14—C13—H13	121.8	C27—C26—H26	120.9
N6—C14—C13	123.53 (16)	C26—C27—C22	120.37 (17)
N6—C14—H14	118.2	C26—C27—H27	119.8
C13—C14—H14	118.2	C22—C27—H27	119.8
C4—N3—C1—N1	−174.73 (16)	C16—C15—C20—C19	0.4 (3)
C4—N3—C1—N2	6.1 (3)	N4—C15—C20—C19	−178.62 (18)
C5—N1—C1—N3	1.1 (3)	O5—C28—C29—C34	−3.0 (3)
C5—N1—C1—N2	−179.67 (17)	O6—C28—C29—C34	178.90 (16)
C2—N2—C1—N3	−5.1 (3)	O5—C28—C29—C30	174.54 (17)
C2—N2—C1—N1	175.71 (15)	O6—C28—C29—C30	−3.6 (2)
C1—N2—C2—C3	−0.1 (3)	C34—C29—C30—C31	−0.5 (3)
N2—C2—C3—C4	3.6 (3)	C28—C29—C30—C31	−178.06 (16)
C1—N3—C4—C3	−2.2 (3)	C29—C30—C31—C32	−0.5 (3)
C2—C3—C4—N3	−2.4 (3)	C30—C31—C32—C33	1.2 (3)
C1—N1—C5—C10	0.3 (3)	C30—C31—C32—N8	−178.68 (15)
C1—N1—C5—C6	−179.26 (17)	O7—N8—C32—C31	176.93 (16)
C10—C5—C6—C7	−1.1 (3)	O8—N8—C32—C31	−2.5 (2)
N1—C5—C6—C7	178.48 (16)	O7—N8—C32—C33	−3.0 (2)
C5—C6—C7—C8	0.9 (3)	O8—N8—C32—C33	177.59 (16)
C6—C7—C8—C9	0.0 (3)	C31—C32—C33—C34	−0.9 (3)
C7—C8—C9—C10	−0.6 (3)	N8—C32—C33—C34	178.98 (16)
C8—C9—C10—C5	0.4 (3)	C32—C33—C34—C29	−0.1 (3)
C6—C5—C10—C9	0.5 (3)	C30—C29—C34—C33	0.8 (3)
N1—C5—C10—C9	−179.09 (17)	C28—C29—C34—C33	178.42 (17)
C14—N6—C11—N5	−0.4 (3)	O1—C21—C22—C27	−10.3 (3)
C14—N6—C11—N4	179.87 (16)	O2—C21—C22—C27	170.65 (16)
C12—N5—C11—N6	0.7 (3)	O1—C21—C22—C23	167.62 (17)
C12—N5—C11—N4	−179.51 (16)	O2—C21—C22—C23	−11.4 (2)
C15—N4—C11—N6	−1.8 (3)	C27—C22—C23—C24	0.6 (3)
C15—N4—C11—N5	178.41 (17)	C21—C22—C23—C24	−177.32 (17)
C11—N5—C12—C13	0.1 (3)	C22—C23—C24—C25	0.2 (3)
N5—C12—C13—C14	−1.2 (3)	C23—C24—C25—C26	−1.2 (3)
C11—N6—C14—C13	−0.8 (3)	C23—C24—C25—N7	178.25 (16)
C12—C13—C14—N6	1.5 (3)	O3—N7—C25—C24	−176.83 (18)
C11—N4—C15—C20	−5.3 (3)	O4—N7—C25—C24	2.5 (3)
C11—N4—C15—C16	175.72 (18)	O3—N7—C25—C26	2.7 (3)
C20—C15—C16—C17	−0.6 (3)	O4—N7—C25—C26	−178.00 (18)
N4—C15—C16—C17	178.45 (17)	C24—C25—C26—C27	1.4 (3)
C15—C16—C17—C18	0.5 (3)	N7—C25—C26—C27	−178.10 (16)
C16—C17—C18—C19	−0.1 (3)	C25—C26—C27—C22	−0.5 (3)
C17—C18—C19—C20	−0.2 (3)	C23—C22—C27—C26	−0.4 (3)
C18—C19—C20—C15	0.0 (3)	C21—C22—C27—C26	177.51 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2o···N2	0.866 (9)	1.698 (10)	2.5581 (18)	171 (2)
O6—H6o···N5	0.853 (9)	1.777 (10)	2.6230 (18)	171 (2)
N1—H1n···O1	0.876 (9)	2.147 (10)	3.0217 (18)	176.3 (17)
N4—H4n···O5	0.881 (9)	2.138 (10)	3.0190 (19)	179.6 (19)
C2—H2···O8	0.95	2.41	3.201 (2)	141
C12—H12···O4	0.95	2.43	3.106 (2)	128
C18—H18···O7i	0.95	2.56	3.330 (2)	138
C19—H19···O3ii	0.95	2.60	3.518 (2)	163
C31—H31···O8iii	0.95	2.55	3.238 (2)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2o⋯N2	0.87 (1)	1.70 (1)	2.5581 (18)	171 (2)
O6—H6o⋯N5	0.85 (1)	1.78 (1)	2.6230 (18)	171 (2)
N1—H1n⋯O1	0.88 (1)	2.15 (1)	3.0217 (18)	176 (2)
N4—H4n⋯O5	0.88 (1)	2.14 (1)	3.0190 (19)	180 (2)
C2—H2⋯O8	0.95	2.41	3.201 (2)	141
C12—H12⋯O4	0.95	2.43	3.106 (2)	128
C18—H18⋯O7i	0.95	2.56	3.330 (2)	138
C19—H19⋯O3ii	0.95	2.60	3.518 (2)	163
C31—H31⋯O8iii	0.95	2.55	3.238 (2)	129

Symmetry codes: (i) ; (ii) ; (iii) .