(E)-1-[2-(2-Cyano-phen-yl)diazen-2-ium-1-yl]naphthalen-2-olate.

There are two independent zwitterion mol-ecules (A and B) in the asymmetric unit of the title compound, C17H11N3O, which belongs to the family of azo dyes. The dihedral angle between the benzene ring and the naphthalene ring system is 6.99 (6)° in mol-ecule A and 4.38 (6)° in mol-ecule B. The azo group adopts an E conformation with respect to the -N=N- bond and each of the independent mol-ecules has an intra-molecular N-H⋯O hydrogen bond. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯N hydrogen bonds, forming ribbons propagating along [-110]. The ribbons are linked via π-π inter-actions involving the benzene and naphthalene rings of inversion-related A and inversion-related B mol-ecules, forming a three-dimensional structure. The most significant centroid-centroid distances vary from 3.6599 (6) to 3.7538 (9) Å.

Related literature

For general background to azo compounds and their use in dyes, pigments and advanced materials, see: Lee et al. (2004 ▶); Oueslati et al. (2004 ▶). Many azo compounds have been synthesized by diazo­tization and diazo coupling reactions, see: Wang et al. (2003 ▶). For a related structure, see: Rãdulescu et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H11N3O

M = 273.29

Triclinic,

a = 7.1296 (3) Å

b = 12.9532 (7) Å

c = 15.6181 (8) Å

α = 111.562 (2)°

β = 90.536 (2)°

γ = 100.779 (2)°

V = 1312.92 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 150 K

0.55 × 0.11 × 0.08 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.910, T max = 0.993

18729 measured reflections

6021 independent reflections

3859 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.120

S = 1.06

6021 reflections

387 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813017261/su2616sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813017261/su2616Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813017261/su2616Isup3.cml

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

C17H11N3O	Z = 4
Mr = 273.29	F(000) = 568
Triclinic, P1	Dx = 1.383 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1296 (3) Å	Cell parameters from 4069 reflections
b = 12.9532 (7) Å	θ = 2.7–27.2°
c = 15.6181 (8) Å	µ = 0.09 mm−1
α = 111.562 (2)°	T = 150 K
β = 90.536 (2)°	Rod, orange
γ = 100.779 (2)°	0.55 × 0.11 × 0.08 mm
V = 1312.92 (11) Å3

Bruker APEXII diffractometer	6021 independent reflections
Radiation source: fine-focus sealed tube	3859 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
CCD rotation images, thin slices scans	θmax = 27.6°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −9→8
Tmin = 0.910, Tmax = 0.993	k = −15→16
18729 measured reflections	l = −20→19

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0552P)2] where P = (Fo2 + 2Fc2)/3
6021 reflections	(Δ/σ)max < 0.001
387 parameters	Δρmax = 0.20 e Å−3
2 restraints	Δρmin = −0.23 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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 > 2sigma(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	0.22974 (15)	−0.08495 (9)	−0.19945 (7)	0.0353 (4)
N1	0.26603 (15)	−0.03201 (9)	−0.00509 (8)	0.0228 (4)
N2	0.28634 (16)	−0.13393 (10)	−0.05950 (8)	0.0240 (4)
N3	0.2868 (2)	−0.37222 (11)	−0.25733 (9)	0.0395 (5)
C1	0.22947 (18)	0.03886 (11)	−0.04340 (9)	0.0214 (4)
C2	0.2066 (2)	0.00985 (13)	−0.14333 (10)	0.0273 (5)
C3	0.1577 (2)	0.09342 (13)	−0.17514 (10)	0.0322 (5)
C4	0.1391 (2)	0.19509 (13)	−0.11610 (10)	0.0323 (5)
C5	0.16559 (19)	0.22862 (12)	−0.01740 (10)	0.0258 (5)
C6	0.1453 (2)	0.33609 (13)	0.04241 (11)	0.0323 (5)
C7	0.1666 (2)	0.36735 (13)	0.13627 (11)	0.0343 (5)
C8	0.2071 (2)	0.29038 (13)	0.17290 (10)	0.0318 (5)
C9	0.2267 (2)	0.18361 (12)	0.11562 (10)	0.0265 (5)
C10	0.20812 (18)	0.15051 (11)	0.01973 (9)	0.0221 (4)
C11	0.31180 (18)	−0.21245 (11)	−0.02079 (9)	0.0221 (4)
C12	0.31961 (19)	−0.32258 (12)	−0.08066 (9)	0.0246 (4)
C13	0.3380 (2)	−0.40431 (12)	−0.04526 (10)	0.0307 (5)
C14	0.3500 (2)	−0.37679 (13)	0.04877 (11)	0.0336 (5)
C15	0.3436 (2)	−0.26761 (12)	0.10790 (10)	0.0302 (5)
C16	0.32483 (19)	−0.18560 (12)	0.07411 (9)	0.0252 (4)
C17	0.3020 (2)	−0.35134 (12)	−0.17923 (11)	0.0287 (5)
O2	0.25056 (17)	−0.07164 (10)	0.29923 (7)	0.0412 (4)
N4	0.23605 (16)	−0.01608 (10)	0.49355 (8)	0.0263 (4)
N5	0.15976 (18)	−0.12048 (10)	0.43789 (8)	0.0287 (4)
N6	−0.0106 (2)	−0.36198 (11)	0.23897 (9)	0.0409 (5)
C18	0.3133 (2)	0.05720 (12)	0.45560 (10)	0.0259 (5)
C19	0.3193 (2)	0.02819 (14)	0.35679 (10)	0.0320 (5)
C20	0.4066 (2)	0.11518 (15)	0.32526 (11)	0.0381 (6)
C21	0.4765 (2)	0.22096 (15)	0.38446 (11)	0.0391 (6)
C22	0.4725 (2)	0.25414 (13)	0.48296 (11)	0.0317 (5)
C23	0.5459 (2)	0.36558 (14)	0.54297 (13)	0.0426 (6)
C24	0.5446 (2)	0.39650 (14)	0.63640 (13)	0.0428 (6)
C25	0.4710 (2)	0.31589 (14)	0.67273 (11)	0.0391 (6)
C26	0.3963 (2)	0.20554 (13)	0.61554 (10)	0.0319 (5)
C27	0.3940 (2)	0.17243 (12)	0.51944 (10)	0.0272 (5)
C28	0.0844 (2)	−0.19913 (12)	0.47635 (10)	0.0257 (5)
C29	−0.0006 (2)	−0.30904 (12)	0.41620 (9)	0.0275 (5)
C30	−0.0778 (2)	−0.39107 (13)	0.45099 (10)	0.0319 (5)
C31	−0.0682 (2)	−0.36403 (13)	0.54521 (10)	0.0338 (5)
C32	0.0176 (2)	−0.25528 (13)	0.60442 (10)	0.0328 (5)
C33	0.0925 (2)	−0.17330 (13)	0.57078 (10)	0.0292 (5)
C34	−0.0066 (2)	−0.33815 (12)	0.31768 (11)	0.0314 (5)
H2	0.272 (2)	−0.1545 (14)	−0.1223 (6)	0.052 (5)*
H3	0.13860	0.07610	−0.23830	0.0390*
H4	0.10770	0.24650	−0.13970	0.0390*
H6	0.11680	0.38740	0.01790	0.0390*
H7	0.15390	0.43950	0.17520	0.0410*
H8	0.22120	0.31110	0.23660	0.0380*
H9	0.25270	0.13280	0.14120	0.0320*
H13	0.34210	−0.47760	−0.08500	0.0370*
H14	0.36250	−0.43140	0.07260	0.0400*
H15	0.35200	−0.24960	0.17140	0.0360*
H16	0.32090	−0.11260	0.11450	0.0300*
H5	0.171 (3)	−0.1310 (16)	0.3780 (7)	0.075 (7)*
H20	0.41490	0.09770	0.26230	0.0460*
H21	0.52990	0.27530	0.36110	0.0470*
H23	0.59660	0.41960	0.51880	0.0510*
H24	0.59290	0.47120	0.67550	0.0510*
H25	0.47210	0.33670	0.73640	0.0470*
H26	0.34690	0.15250	0.64090	0.0380*
H30	−0.13560	−0.46380	0.41090	0.0380*
H31	−0.11910	−0.41850	0.56890	0.0410*
H32	0.02470	−0.23750	0.66790	0.0390*
H33	0.14840	−0.10060	0.61140	0.0350*

	U11	U22	U33	U12	U13	U23
O1	0.0424 (7)	0.0354 (7)	0.0234 (6)	0.0079 (5)	0.0014 (5)	0.0058 (5)
N1	0.0197 (6)	0.0200 (7)	0.0252 (7)	0.0027 (5)	0.0010 (5)	0.0052 (5)
N2	0.0251 (6)	0.0214 (7)	0.0227 (7)	0.0043 (5)	0.0006 (5)	0.0054 (6)
N3	0.0474 (9)	0.0325 (8)	0.0325 (8)	0.0039 (7)	0.0031 (6)	0.0074 (7)
C1	0.0166 (7)	0.0232 (8)	0.0238 (8)	0.0011 (6)	−0.0008 (6)	0.0095 (7)
C2	0.0234 (7)	0.0285 (9)	0.0265 (9)	0.0016 (6)	0.0009 (6)	0.0083 (7)
C3	0.0324 (8)	0.0399 (10)	0.0267 (9)	0.0072 (7)	−0.0018 (7)	0.0155 (8)
C4	0.0282 (8)	0.0364 (10)	0.0379 (10)	0.0053 (7)	−0.0016 (7)	0.0210 (8)
C5	0.0178 (7)	0.0281 (9)	0.0328 (9)	0.0029 (6)	−0.0002 (6)	0.0139 (7)
C6	0.0252 (8)	0.0265 (9)	0.0484 (11)	0.0055 (7)	0.0010 (7)	0.0177 (8)
C7	0.0278 (8)	0.0248 (9)	0.0456 (10)	0.0060 (7)	0.0062 (7)	0.0075 (8)
C8	0.0301 (8)	0.0303 (9)	0.0298 (9)	0.0030 (7)	0.0054 (7)	0.0069 (7)
C9	0.0261 (8)	0.0243 (8)	0.0291 (9)	0.0038 (6)	0.0027 (6)	0.0108 (7)
C10	0.0153 (7)	0.0219 (8)	0.0273 (8)	0.0008 (6)	0.0004 (6)	0.0088 (6)
C11	0.0181 (7)	0.0211 (8)	0.0259 (8)	0.0028 (6)	0.0017 (6)	0.0080 (6)
C12	0.0219 (7)	0.0220 (8)	0.0269 (8)	0.0028 (6)	0.0017 (6)	0.0065 (7)
C13	0.0300 (8)	0.0220 (8)	0.0363 (9)	0.0050 (7)	0.0018 (7)	0.0067 (7)
C14	0.0347 (9)	0.0284 (9)	0.0433 (10)	0.0074 (7)	0.0013 (7)	0.0195 (8)
C15	0.0311 (8)	0.0323 (9)	0.0282 (9)	0.0062 (7)	0.0013 (7)	0.0126 (7)
C16	0.0245 (7)	0.0232 (8)	0.0252 (8)	0.0044 (6)	0.0017 (6)	0.0062 (7)
C17	0.0284 (8)	0.0205 (8)	0.0320 (10)	0.0025 (6)	0.0037 (7)	0.0050 (7)
O2	0.0551 (8)	0.0418 (7)	0.0233 (6)	0.0147 (6)	0.0010 (5)	0.0060 (5)
N4	0.0251 (6)	0.0258 (7)	0.0259 (7)	0.0089 (6)	−0.0009 (5)	0.0057 (6)
N5	0.0338 (7)	0.0263 (8)	0.0235 (7)	0.0094 (6)	−0.0001 (6)	0.0051 (6)
N6	0.0539 (9)	0.0338 (8)	0.0313 (8)	0.0092 (7)	0.0007 (7)	0.0080 (7)
C18	0.0229 (7)	0.0304 (9)	0.0253 (8)	0.0099 (7)	0.0005 (6)	0.0094 (7)
C19	0.0297 (8)	0.0395 (10)	0.0279 (9)	0.0149 (7)	0.0015 (7)	0.0101 (8)
C20	0.0339 (9)	0.0548 (12)	0.0313 (9)	0.0139 (8)	0.0054 (7)	0.0205 (9)
C21	0.0290 (9)	0.0493 (11)	0.0477 (11)	0.0067 (8)	0.0043 (7)	0.0287 (9)
C22	0.0209 (7)	0.0348 (10)	0.0395 (10)	0.0049 (7)	−0.0011 (7)	0.0145 (8)
C23	0.0281 (9)	0.0403 (11)	0.0610 (13)	0.0001 (8)	−0.0067 (8)	0.0245 (10)
C24	0.0346 (9)	0.0293 (10)	0.0554 (12)	0.0027 (8)	−0.0123 (8)	0.0077 (9)
C25	0.0367 (9)	0.0383 (11)	0.0342 (10)	0.0112 (8)	−0.0100 (7)	0.0029 (8)
C26	0.0312 (8)	0.0320 (10)	0.0306 (9)	0.0096 (7)	−0.0025 (7)	0.0082 (8)
C27	0.0206 (7)	0.0299 (9)	0.0305 (9)	0.0093 (7)	−0.0009 (6)	0.0086 (7)
C28	0.0249 (8)	0.0266 (9)	0.0264 (8)	0.0109 (7)	−0.0003 (6)	0.0084 (7)
C29	0.0287 (8)	0.0285 (9)	0.0233 (8)	0.0117 (7)	−0.0031 (6)	0.0047 (7)
C30	0.0314 (8)	0.0253 (9)	0.0339 (9)	0.0063 (7)	−0.0050 (7)	0.0054 (7)
C31	0.0349 (9)	0.0308 (9)	0.0353 (10)	0.0040 (7)	−0.0028 (7)	0.0133 (8)
C32	0.0323 (9)	0.0379 (10)	0.0270 (9)	0.0068 (7)	−0.0018 (7)	0.0113 (8)
C33	0.0287 (8)	0.0259 (9)	0.0282 (9)	0.0066 (7)	−0.0031 (6)	0.0042 (7)
C34	0.0347 (9)	0.0244 (9)	0.0329 (10)	0.0096 (7)	−0.0023 (7)	0.0066 (7)

O1—C2	1.261 (2)	C8—H8	0.9300
O2—C19	1.273 (2)	C9—H9	0.9300
N1—N2	1.3173 (17)	C13—H13	0.9300
N1—C1	1.3263 (19)	C14—H14	0.9300
N2—C11	1.397 (2)	C15—H15	0.9300
N3—C17	1.148 (2)	C16—H16	0.9300
N2—H2	0.916 (9)	C18—C27	1.459 (2)
N4—N5	1.3162 (18)	C18—C19	1.451 (2)
N4—C18	1.334 (2)	C19—C20	1.432 (3)
N5—C28	1.392 (2)	C20—C21	1.336 (3)
N6—C34	1.151 (2)	C21—C22	1.439 (2)
N5—H5	0.901 (12)	C22—C27	1.409 (2)
C1—C10	1.457 (2)	C22—C23	1.396 (3)
C1—C2	1.465 (2)	C23—C24	1.365 (3)
C2—C3	1.440 (2)	C24—C25	1.387 (3)
C3—C4	1.333 (2)	C25—C26	1.376 (2)
C4—C5	1.440 (2)	C26—C27	1.400 (2)
C5—C6	1.398 (2)	C28—C33	1.385 (2)
C5—C10	1.412 (2)	C28—C29	1.400 (2)
C6—C7	1.368 (2)	C29—C30	1.392 (2)
C7—C8	1.389 (2)	C29—C34	1.442 (2)
C8—C9	1.378 (2)	C30—C31	1.380 (2)
C9—C10	1.396 (2)	C31—C32	1.387 (2)
C11—C16	1.3903 (19)	C32—C33	1.376 (2)
C11—C12	1.401 (2)	C20—H20	0.9300
C12—C13	1.387 (2)	C21—H21	0.9300
C12—C17	1.443 (2)	C23—H23	0.9300
C13—C14	1.376 (2)	C24—H24	0.9300
C14—C15	1.386 (2)	C25—H25	0.9300
C15—C16	1.374 (2)	C26—H26	0.9300
C3—H3	0.9300	C30—H30	0.9300
C4—H4	0.9300	C31—H31	0.9300
C6—H6	0.9300	C32—H32	0.9300
C7—H7	0.9300	C33—H33	0.9300
N2—N1—C1	118.56 (12)	C14—C15—H15	119.00
N1—N2—C11	119.42 (11)	C16—C15—H15	120.00
C11—N2—H2	120.8 (11)	C11—C16—H16	120.00
N1—N2—H2	119.5 (11)	C15—C16—H16	120.00
N5—N4—C18	117.91 (12)	C19—C18—C27	119.88 (14)
N4—N5—C28	118.70 (12)	N4—C18—C27	116.30 (13)
N4—N5—H5	112.2 (13)	N4—C18—C19	123.82 (14)
C28—N5—H5	129.0 (13)	O2—C19—C18	121.45 (16)
N1—C1—C10	116.45 (12)	O2—C19—C20	120.47 (14)
C2—C1—C10	119.75 (13)	C18—C19—C20	118.08 (15)
N1—C1—C2	123.79 (13)	C19—C20—C21	121.38 (15)
O1—C2—C1	121.04 (14)	C20—C21—C22	122.62 (17)
O1—C2—C3	121.26 (13)	C21—C22—C27	119.33 (15)
C1—C2—C3	117.70 (14)	C23—C22—C27	119.46 (15)
C2—C3—C4	121.48 (14)	C21—C22—C23	121.21 (16)
C3—C4—C5	122.80 (15)	C22—C23—C24	121.13 (17)
C6—C5—C10	119.37 (13)	C23—C24—C25	119.63 (17)
C4—C5—C6	121.21 (15)	C24—C25—C26	120.72 (15)
C4—C5—C10	119.40 (14)	C25—C26—C27	120.53 (16)
C5—C6—C7	121.32 (16)	C22—C27—C26	118.51 (15)
C6—C7—C8	119.39 (15)	C18—C27—C26	122.81 (15)
C7—C8—C9	120.57 (14)	C18—C27—C22	118.67 (13)
C8—C9—C10	120.99 (14)	N5—C28—C29	117.98 (13)
C1—C10—C9	122.83 (13)	N5—C28—C33	122.77 (14)
C5—C10—C9	118.36 (13)	C29—C28—C33	119.25 (15)
C1—C10—C5	118.81 (12)	C28—C29—C30	120.34 (13)
N2—C11—C12	118.15 (12)	C30—C29—C34	119.64 (14)
N2—C11—C16	122.33 (13)	C28—C29—C34	120.02 (14)
C12—C11—C16	119.50 (14)	C29—C30—C31	119.69 (15)
C11—C12—C17	119.62 (14)	C30—C31—C32	119.71 (16)
C13—C12—C17	120.29 (14)	C31—C32—C33	121.05 (14)
C11—C12—C13	120.06 (12)	C28—C33—C32	119.96 (15)
C12—C13—C14	119.88 (14)	N6—C34—C29	179.50 (17)
C13—C14—C15	119.98 (16)	C19—C20—H20	119.00
C14—C15—C16	120.98 (14)	C21—C20—H20	119.00
C11—C16—C15	119.60 (14)	C20—C21—H21	119.00
N3—C17—C12	178.63 (17)	C22—C21—H21	119.00
C4—C3—H3	119.00	C22—C23—H23	119.00
C2—C3—H3	119.00	C24—C23—H23	119.00
C5—C4—H4	119.00	C23—C24—H24	120.00
C3—C4—H4	119.00	C25—C24—H24	120.00
C5—C6—H6	119.00	C24—C25—H25	120.00
C7—C6—H6	119.00	C26—C25—H25	120.00
C6—C7—H7	120.00	C25—C26—H26	120.00
C8—C7—H7	120.00	C27—C26—H26	120.00
C9—C8—H8	120.00	C29—C30—H30	120.00
C7—C8—H8	120.00	C31—C30—H30	120.00
C10—C9—H9	119.00	C30—C31—H31	120.00
C8—C9—H9	120.00	C32—C31—H31	120.00
C12—C13—H13	120.00	C31—C32—H32	119.00
C14—C13—H13	120.00	C33—C32—H32	119.00
C13—C14—H14	120.00	C28—C33—H33	120.00
C15—C14—H14	120.00	C32—C33—H33	120.00
C1—N1—N2—C11	−175.64 (12)	C11—C12—C13—C14	−0.5 (2)
N2—N1—C1—C2	1.2 (2)	C17—C12—C13—C14	−178.41 (14)
N2—N1—C1—C10	179.96 (12)	C12—C13—C14—C15	0.0 (2)
N1—N2—C11—C12	175.62 (12)	C13—C14—C15—C16	0.2 (2)
N1—N2—C11—C16	−2.8 (2)	C14—C15—C16—C11	0.1 (2)
N5—N4—C18—C27	179.18 (13)	N4—C18—C19—O2	−0.5 (2)
C18—N4—N5—C28	177.81 (13)	N4—C18—C19—C20	180.00 (15)
N5—N4—C18—C19	−0.5 (2)	C27—C18—C19—O2	179.83 (14)
N4—N5—C28—C29	178.40 (13)	C27—C18—C19—C20	0.3 (2)
N4—N5—C28—C33	−2.4 (2)	N4—C18—C27—C22	−178.20 (13)
C10—C1—C2—O1	177.94 (13)	N4—C18—C27—C26	1.6 (2)
C10—C1—C2—C3	−1.8 (2)	C19—C18—C27—C22	1.5 (2)
N1—C1—C2—O1	−3.3 (2)	C19—C18—C27—C26	−178.72 (14)
N1—C1—C2—C3	176.96 (13)	O2—C19—C20—C21	178.79 (15)
C2—C1—C10—C9	179.57 (13)	C18—C19—C20—C21	−1.7 (2)
N1—C1—C10—C5	−178.85 (12)	C19—C20—C21—C22	1.2 (2)
N1—C1—C10—C9	0.7 (2)	C20—C21—C22—C23	−179.67 (15)
C2—C1—C10—C5	0.0 (2)	C20—C21—C22—C27	0.7 (2)
O1—C2—C3—C4	−177.83 (15)	C21—C22—C23—C24	−179.01 (14)
C1—C2—C3—C4	1.9 (2)	C27—C22—C23—C24	0.6 (2)
C2—C3—C4—C5	−0.2 (2)	C21—C22—C27—C18	−2.0 (2)
C3—C4—C5—C10	−1.8 (2)	C21—C22—C27—C26	178.21 (14)
C3—C4—C5—C6	179.86 (15)	C23—C22—C27—C18	178.35 (14)
C6—C5—C10—C9	0.6 (2)	C23—C22—C27—C26	−1.4 (2)
C4—C5—C10—C1	1.8 (2)	C22—C23—C24—C25	0.7 (2)
C4—C5—C6—C7	178.66 (14)	C23—C24—C25—C26	−1.1 (2)
C10—C5—C6—C7	0.3 (2)	C24—C25—C26—C27	0.3 (2)
C4—C5—C10—C9	−177.84 (13)	C25—C26—C27—C18	−178.79 (14)
C6—C5—C10—C1	−179.82 (13)	C25—C26—C27—C22	1.0 (2)
C5—C6—C7—C8	−0.7 (2)	N5—C28—C29—C30	179.85 (13)
C6—C7—C8—C9	0.3 (2)	N5—C28—C29—C34	0.6 (2)
C7—C8—C9—C10	0.6 (2)	C33—C28—C29—C30	0.7 (2)
C8—C9—C10—C1	179.42 (14)	C33—C28—C29—C34	−178.65 (14)
C8—C9—C10—C5	−1.0 (2)	N5—C28—C33—C32	−179.13 (14)
C16—C11—C12—C13	0.7 (2)	C29—C28—C33—C32	0.0 (2)
C16—C11—C12—C17	178.68 (13)	C28—C29—C30—C31	−0.8 (2)
N2—C11—C12—C17	0.2 (2)	C34—C29—C30—C31	178.51 (14)
N2—C11—C12—C13	−177.75 (13)	C29—C30—C31—C32	0.2 (2)
C12—C11—C16—C15	−0.5 (2)	C30—C31—C32—C33	0.4 (2)
N2—C11—C16—C15	177.89 (13)	C31—C32—C33—C28	−0.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.92 (1)	1.80 (2)	2.5380 (16)	136 (2)
N5—H5···O2	0.90 (1)	1.72 (2)	2.5277 (17)	147 (2)
C21—H21···N3i	0.93	2.61	3.509 (2)	162
C30—H30···N3ii	0.93	2.60	3.487 (2)	159
C32—H32···O1iii	0.93	2.49	3.1994 (18)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.92 (1)	1.80 (2)	2.5380 (16)	136 (2)
N5—H5⋯O2	0.90 (1)	1.72 (2)	2.5277 (17)	147 (2)
C21—H21⋯N3i	0.93	2.61	3.509 (2)	162
C30—H30⋯N3ii	0.93	2.60	3.487 (2)	159
C32—H32⋯O1iii	0.93	2.49	3.1994 (18)	133

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