Tris(2-benzamido-eth-yl)ammonium tetra-fluoro-borate.

In the title compound, C(27)H(31)N(4)O(3) (+)·BF(4) (-), the central N atom is protonated. The three arms form a pocket and one amidic O atom accepts an inter-molecular hydrogen bond with the protonated amine. The tetra-fluoro-borate anion is outside the cavity and is hydrogen bonded to one amide N atom. Adjacent organic cations are connected by a pair of N-H⋯O hydrogen bonds, forming a chain.

Related literature

For general background to tris­(amino­eth­yl)–amine and its binding of anions, see: Bianchi et al. (1997 ▶); Kang et al. (2005 ▶); Hossain,(2008 ▶); For related structures, see: Bazzicalupi et al. (2009 ▶); Hossain et al. (2004 ▶); Burgess et al. (1991 ▶), Lo & Ng (2008 ▶); Saeed et al. (2010 ▶).

Experimental

Crystal data

C27H31N4O3 +·n class="Chemical">BF4 −

M = 546.37

Monoclinic,

a = 13.325 (2) Å

b = 9.572 (2) Å

c = 21.118 (3) Å

β = 94.546 (10)°

V = 2685.1 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 90 K

0.27 × 0.25 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer with Oxford Cryostream

31844 measured reflections

5914 independent reflections

3310 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.114

S = 1.00

5914 reflections

365 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.27 e Å−3

Data collection: COLLECT (Nonius, 1999 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024323/rk2214sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024323/rk2214Isup2.hkl

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

C27H31N4O3+·BF4−	F(000) = 1144
Mr = 546.37	Dx = 1.352 Mg m−3
Monoclinic, P21/n	Melting point: 423 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 13.325 (2) Å	Cell parameters from 6170 reflections
b = 9.572 (2) Å	θ = 2.5–27.1°
c = 21.118 (3) Å	µ = 0.11 mm−1
β = 94.546 (10)°	T = 90 K
V = 2685.1 (8) Å3	Block, colourless
Z = 4	0.27 × 0.25 × 0.10 mm

Nonius KappaCCD diffractometer with Oxford Cryostream	3310 reflections with I > 2σ(I)
Radiation source: fine–focus sealed tube	Rint = 0.068
graphite	θmax = 27.1°, θmin = 2.6°
ω–scans with κ–offsets	h = −17→17
31844 measured reflections	k = −12→12
5914 independent reflections	l = −27→26

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.114	w = 1/[σ2(Fo2) + (0.0492P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
5914 reflections	Δρmax = 0.26 e Å−3
365 parameters	Δρmin = −0.27 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0047 (7)

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	0.69598 (10)	0.66708 (15)	0.51248 (6)	0.0235 (3)
O2	0.97004 (10)	0.65535 (14)	0.51217 (6)	0.0237 (3)
O3	0.66033 (11)	0.35955 (15)	0.42976 (6)	0.0269 (4)
N1	0.77743 (12)	0.52786 (18)	0.61191 (7)	0.0190 (4)
H1N	0.7663 (14)	0.584 (2)	0.5718 (9)	0.023*
N2	0.55317 (13)	0.65036 (19)	0.56356 (7)	0.0227 (4)
H2N	0.4881 (16)	0.655 (2)	0.5611 (9)	0.027*
N3	0.89693 (13)	0.78188 (18)	0.58685 (7)	0.0207 (4)
H3N	0.8721 (15)	0.867 (2)	0.5972 (9)	0.025*
N4	0.81500 (13)	0.39353 (18)	0.47972 (7)	0.0204 (4)
H4N	0.8780 (16)	0.412 (2)	0.4753 (9)	0.024*
C1	0.67293 (15)	0.4962 (2)	0.63108 (9)	0.0212 (5)
H1A	0.6782	0.4611	0.6753	0.025*
H1B	0.6432	0.4208	0.6035	0.025*
C2	0.60230 (16)	0.6219 (2)	0.62667 (8)	0.0238 (5)
H2A	0.5495	0.6073	0.6564	0.029*
H2B	0.6412	0.7058	0.6411	0.029*
C3	0.60327 (16)	0.6812 (2)	0.51281 (9)	0.0208 (5)
C4	0.54443 (15)	0.7377 (2)	0.45532 (9)	0.0203 (5)
C5	0.46519 (16)	0.8306 (2)	0.45962 (9)	0.0243 (5)
H5	0.4442	0.8555	0.5001	0.029*
C6	0.41677 (16)	0.8870 (2)	0.40503 (10)	0.0293 (5)
H6	0.3632	0.9516	0.4081	0.035*
C7	0.44618 (16)	0.8496 (2)	0.34635 (10)	0.0310 (6)
H7	0.4121	0.8875	0.3090	0.037*
C8	0.52504 (17)	0.7572 (2)	0.34138 (10)	0.0312 (6)
H8	0.5447	0.7313	0.3008	0.037*
C9	0.57503 (16)	0.7029 (2)	0.39571 (9)	0.0269 (5)
H9	0.6305	0.6417	0.3924	0.032*
C10	0.83608 (15)	0.6116 (2)	0.66272 (9)	0.0218 (5)
H10A	0.8600	0.5483	0.6978	0.026*
H10B	0.7908	0.6814	0.6801	0.026*
C11	0.92603 (15)	0.6867 (2)	0.63859 (9)	0.0224 (5)
H11A	0.9612	0.7398	0.6740	0.027*
H11B	0.9737	0.6168	0.6239	0.027*
C12	0.92266 (15)	0.7599 (2)	0.52720 (9)	0.0197 (5)
C13	0.88929 (15)	0.8684 (2)	0.47918 (9)	0.0191 (5)
C14	0.80176 (16)	0.9456 (2)	0.48281 (9)	0.0237 (5)
H14	0.7618	0.9325	0.5176	0.028*
C15	0.77232 (17)	1.0423 (2)	0.43572 (9)	0.0270 (5)
H15	0.7120	1.0942	0.4382	0.032*
C16	0.83094 (17)	1.0627 (2)	0.38534 (9)	0.0267 (5)
H16	0.8112	1.1296	0.3535	0.032*
C17	0.91824 (17)	0.9861 (2)	0.38106 (9)	0.0272 (5)
H17	0.9583	1.0000	0.3463	0.033*
C18	0.94687 (16)	0.8890 (2)	0.42784 (9)	0.0231 (5)
H18	1.0065	0.8359	0.4248	0.028*
C19	0.83279 (16)	0.3959 (2)	0.59740 (8)	0.0211 (5)
H19A	0.8299	0.3309	0.6337	0.025*
H19B	0.9045	0.4192	0.5935	0.025*
C20	0.79230 (16)	0.3222 (2)	0.53764 (8)	0.0223 (5)
H20A	0.8210	0.2268	0.5374	0.027*
H20B	0.7184	0.3131	0.5381	0.027*
C21	0.74826 (15)	0.4008 (2)	0.42910 (9)	0.0199 (5)
C22	0.78649 (15)	0.4566 (2)	0.36920 (9)	0.0211 (5)
C23	0.86024 (15)	0.5588 (2)	0.36906 (9)	0.0228 (5)
H23	0.8870	0.5989	0.4080	0.027*
C24	0.89490 (16)	0.6025 (2)	0.31219 (9)	0.0280 (5)
H24	0.9440	0.6746	0.3122	0.034*
C25	0.85853 (18)	0.5420 (2)	0.25530 (9)	0.0308 (6)
H25	0.8844	0.5699	0.2166	0.037*
C26	0.78424 (18)	0.4403 (2)	0.25513 (10)	0.0338 (6)
H26	0.7589	0.3986	0.2163	0.041*
C27	0.74720 (17)	0.4001 (2)	0.31173 (9)	0.0274 (5)
H27	0.6945	0.3332	0.3114	0.033*
B1	0.8258 (2)	1.0373 (3)	0.69733 (11)	0.0262 (6)
F1	0.74417 (10)	0.95062 (13)	0.70473 (5)	0.0393 (4)
F2	0.81014 (10)	1.16644 (13)	0.72363 (5)	0.0396 (4)
F3	0.83701 (9)	1.05339 (12)	0.63193 (5)	0.0297 (3)
F4	0.91193 (10)	0.97574 (15)	0.72626 (5)	0.0444 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0192 (9)	0.0295 (9)	0.0217 (7)	0.0012 (7)	0.0004 (6)	0.0045 (6)
O2	0.0247 (9)	0.0212 (9)	0.0252 (8)	0.0040 (7)	0.0008 (6)	−0.0025 (6)
O3	0.0196 (9)	0.0279 (9)	0.0329 (8)	0.0000 (7)	0.0000 (6)	0.0030 (7)
N1	0.0182 (10)	0.0217 (10)	0.0169 (9)	−0.0006 (8)	−0.0003 (7)	0.0011 (7)
N2	0.0147 (10)	0.0320 (11)	0.0213 (9)	0.0018 (9)	0.0014 (8)	0.0021 (8)
N3	0.0235 (11)	0.0182 (10)	0.0201 (9)	0.0020 (8)	0.0010 (7)	0.0013 (8)
N4	0.0170 (10)	0.0250 (10)	0.0192 (9)	−0.0013 (9)	0.0013 (8)	−0.0006 (8)
C1	0.0182 (12)	0.0258 (13)	0.0199 (11)	−0.0029 (10)	0.0034 (8)	0.0007 (9)
C2	0.0230 (12)	0.0304 (13)	0.0181 (11)	0.0016 (10)	0.0027 (9)	0.0003 (9)
C3	0.0210 (13)	0.0188 (12)	0.0223 (11)	−0.0010 (10)	0.0007 (9)	−0.0017 (9)
C4	0.0183 (12)	0.0212 (12)	0.0209 (11)	−0.0012 (10)	−0.0010 (9)	0.0017 (9)
C5	0.0226 (13)	0.0241 (12)	0.0263 (12)	−0.0013 (10)	0.0036 (9)	0.0007 (10)
C6	0.0250 (13)	0.0293 (14)	0.0333 (13)	0.0044 (11)	0.0010 (10)	0.0069 (11)
C7	0.0247 (13)	0.0398 (15)	0.0275 (12)	0.0034 (12)	−0.0040 (10)	0.0123 (11)
C8	0.0321 (14)	0.0391 (15)	0.0224 (12)	0.0044 (12)	0.0024 (10)	0.0050 (10)
C9	0.0231 (13)	0.0292 (14)	0.0283 (12)	0.0022 (10)	0.0021 (9)	0.0023 (10)
C10	0.0237 (12)	0.0236 (12)	0.0173 (10)	−0.0001 (10)	−0.0028 (9)	−0.0019 (9)
C11	0.0212 (12)	0.0236 (12)	0.0218 (11)	0.0013 (10)	−0.0010 (9)	0.0010 (9)
C12	0.0172 (12)	0.0195 (12)	0.0221 (11)	−0.0051 (10)	−0.0012 (9)	−0.0019 (9)
C13	0.0185 (12)	0.0173 (12)	0.0212 (11)	−0.0019 (10)	−0.0004 (8)	−0.0035 (9)
C14	0.0274 (13)	0.0228 (12)	0.0206 (11)	−0.0009 (11)	0.0010 (9)	−0.0039 (10)
C15	0.0284 (13)	0.0226 (13)	0.0292 (12)	0.0035 (11)	−0.0024 (10)	−0.0026 (10)
C16	0.0325 (14)	0.0207 (12)	0.0253 (12)	−0.0028 (11)	−0.0065 (10)	0.0017 (10)
C17	0.0302 (14)	0.0286 (14)	0.0225 (12)	−0.0068 (11)	0.0009 (9)	−0.0002 (10)
C18	0.0206 (12)	0.0225 (12)	0.0261 (11)	−0.0021 (10)	0.0016 (9)	−0.0034 (10)
C19	0.0239 (12)	0.0181 (12)	0.0213 (11)	0.0051 (10)	0.0019 (9)	0.0012 (9)
C20	0.0248 (13)	0.0215 (12)	0.0210 (11)	0.0003 (10)	0.0048 (9)	0.0006 (9)
C21	0.0159 (12)	0.0168 (11)	0.0268 (12)	0.0024 (10)	0.0004 (9)	−0.0039 (9)
C22	0.0184 (12)	0.0216 (12)	0.0225 (11)	0.0055 (10)	−0.0029 (9)	0.0014 (9)
C23	0.0243 (13)	0.0236 (13)	0.0203 (11)	0.0040 (10)	0.0012 (9)	−0.0021 (9)
C24	0.0264 (13)	0.0264 (13)	0.0312 (13)	0.0020 (11)	0.0021 (10)	0.0031 (10)
C25	0.0428 (16)	0.0291 (14)	0.0209 (12)	0.0080 (12)	0.0050 (10)	0.0042 (10)
C26	0.0472 (16)	0.0296 (14)	0.0231 (12)	0.0057 (13)	−0.0079 (11)	0.0007 (10)
C27	0.0294 (14)	0.0230 (13)	0.0285 (12)	−0.0003 (11)	−0.0058 (10)	0.0036 (10)
B1	0.0297 (16)	0.0295 (16)	0.0199 (13)	0.0049 (13)	0.0043 (11)	0.0011 (11)
F1	0.0437 (9)	0.0353 (8)	0.0392 (7)	−0.0023 (7)	0.0056 (6)	0.0090 (6)
F2	0.0628 (10)	0.0305 (8)	0.0269 (7)	0.0042 (7)	0.0127 (6)	−0.0040 (6)
F3	0.0397 (8)	0.0307 (8)	0.0194 (6)	0.0108 (6)	0.0058 (5)	0.0022 (5)
F4	0.0383 (9)	0.0703 (11)	0.0249 (7)	0.0223 (8)	0.0048 (6)	0.0119 (7)

O1—C3	1.243 (2)	C11—H11A	0.9900
O2—C12	1.238 (2)	C11—H11B	0.9900
O3—C21	1.238 (2)	C12—C13	1.495 (3)
N1—C19	1.506 (2)	C13—C14	1.388 (3)
N1—C10	1.507 (2)	C13—C18	1.391 (3)
N1—C1	1.511 (2)	C14—C15	1.392 (3)
N1—H1N	1.003 (19)	C14—H14	0.9500
N2—C3	1.340 (2)	C15—C16	1.383 (3)
N2—C2	1.463 (2)	C15—H15	0.9500
N2—H2N	0.87 (2)	C16—C17	1.384 (3)
N3—C12	1.348 (2)	C16—H16	0.9500
N3—C11	1.452 (2)	C17—C18	1.388 (3)
N3—H3N	0.92 (2)	C17—H17	0.9500
N4—C21	1.337 (2)	C18—H18	0.9500
N4—C20	1.453 (2)	C19—C20	1.508 (3)
N4—H4N	0.87 (2)	C19—H19A	0.9900
C1—C2	1.526 (3)	C19—H19B	0.9900
C1—H1A	0.9900	C20—H20A	0.9900
C1—H1B	0.9900	C20—H20B	0.9900
C2—H2A	0.9900	C21—C22	1.499 (3)
C2—H2B	0.9900	C22—C23	1.387 (3)
C3—C4	1.493 (3)	C22—C27	1.392 (3)
C4—C5	1.389 (3)	C23—C24	1.385 (3)
C4—C9	1.394 (3)	C23—H23	0.9500
C5—C6	1.385 (3)	C24—C25	1.386 (3)
C5—H5	0.9500	C24—H24	0.9500
C6—C7	1.376 (3)	C25—C26	1.388 (3)
C6—H6	0.9500	C25—H25	0.9500
C7—C8	1.384 (3)	C26—C27	1.384 (3)
C7—H7	0.9500	C26—H26	0.9500
C8—C9	1.382 (3)	C27—H27	0.9500
C8—H8	0.9500	B1—F2	1.378 (3)
C9—H9	0.9500	B1—F1	1.387 (3)
C10—C11	1.520 (3)	B1—F4	1.388 (3)
C10—H10A	0.9900	B1—F3	1.409 (2)
C10—H10B	0.9900
C19—N1—C10	110.86 (15)	O2—C12—N3	122.60 (18)
C19—N1—C1	111.27 (16)	O2—C12—C13	121.20 (17)
C10—N1—C1	110.66 (15)	N3—C12—C13	116.19 (18)
C19—N1—H1N	108.6 (11)	C14—C13—C18	119.04 (19)
C10—N1—H1N	110.5 (11)	C14—C13—C12	122.60 (17)
C1—N1—H1N	104.8 (11)	C18—C13—C12	118.33 (18)
C3—N2—C2	123.66 (18)	C13—C14—C15	120.34 (19)
C3—N2—H2N	120.1 (13)	C13—C14—H14	119.8
C2—N2—H2N	115.9 (13)	C15—C14—H14	119.8
C12—N3—C11	122.19 (18)	C16—C15—C14	119.9 (2)
C12—N3—H3N	119.1 (12)	C16—C15—H15	120.0
C11—N3—H3N	117.5 (12)	C14—C15—H15	120.0
C21—N4—C20	121.86 (18)	C15—C16—C17	120.3 (2)
C21—N4—H4N	119.3 (13)	C15—C16—H16	119.9
C20—N4—H4N	116.9 (13)	C17—C16—H16	119.9
N1—C1—C2	113.71 (17)	C16—C17—C18	119.6 (2)
N1—C1—H1A	108.8	C16—C17—H17	120.2
C2—C1—H1A	108.8	C18—C17—H17	120.2
N1—C1—H1B	108.8	C17—C18—C13	120.8 (2)
C2—C1—H1B	108.8	C17—C18—H18	119.6
H1A—C1—H1B	107.7	C13—C18—H18	119.6
N2—C2—C1	115.56 (16)	N1—C19—C20	114.47 (16)
N2—C2—H2A	108.4	N1—C19—H19A	108.6
C1—C2—H2A	108.4	C20—C19—H19A	108.6
N2—C2—H2B	108.4	N1—C19—H19B	108.6
C1—C2—H2B	108.4	C20—C19—H19B	108.6
H2A—C2—H2B	107.5	H19A—C19—H19B	107.6
O1—C3—N2	122.62 (18)	N4—C20—C19	113.57 (17)
O1—C3—C4	119.51 (17)	N4—C20—H20A	108.9
N2—C3—C4	117.86 (18)	C19—C20—H20A	108.9
C5—C4—C9	119.34 (18)	N4—C20—H20B	108.9
C5—C4—C3	122.10 (17)	C19—C20—H20B	108.9
C9—C4—C3	118.41 (19)	H20A—C20—H20B	107.7
C6—C5—C4	120.12 (19)	O3—C21—N4	122.99 (18)
C6—C5—H5	119.9	O3—C21—C22	120.58 (17)
C4—C5—H5	119.9	N4—C21—C22	116.38 (18)
C7—C6—C5	120.0 (2)	C23—C22—C27	119.33 (19)
C7—C6—H6	120.0	C23—C22—C21	122.77 (17)
C5—C6—H6	120.0	C27—C22—C21	117.88 (19)
C6—C7—C8	120.5 (2)	C24—C23—C22	119.99 (19)
C6—C7—H7	119.8	C24—C23—H23	120.0
C8—C7—H7	119.8	C22—C23—H23	120.0
C9—C8—C7	119.8 (2)	C23—C24—C25	120.5 (2)
C9—C8—H8	120.1	C23—C24—H24	119.8
C7—C8—H8	120.1	C25—C24—H24	119.8
C8—C9—C4	120.3 (2)	C24—C25—C26	119.7 (2)
C8—C9—H9	119.9	C24—C25—H25	120.1
C4—C9—H9	119.9	C26—C25—H25	120.1
N1—C10—C11	113.03 (15)	C27—C26—C25	119.7 (2)
N1—C10—H10A	109.0	C27—C26—H26	120.1
C11—C10—H10A	109.0	C25—C26—H26	120.1
N1—C10—H10B	109.0	C26—C27—C22	120.6 (2)
C11—C10—H10B	109.0	C26—C27—H27	119.7
H10A—C10—H10B	107.8	C22—C27—H27	119.7
N3—C11—C10	112.24 (16)	F2—B1—F1	110.24 (19)
N3—C11—H11A	109.2	F2—B1—F4	110.49 (19)
C10—C11—H11A	109.2	F1—B1—F4	108.96 (19)
N3—C11—H11B	109.2	F2—B1—F3	109.16 (19)
C10—C11—H11B	109.2	F1—B1—F3	108.70 (18)
H11A—C11—H11B	107.9	F4—B1—F3	109.26 (18)
C19—N1—C1—C2	−162.24 (15)	N3—C12—C13—C18	151.42 (18)
C10—N1—C1—C2	74.0 (2)	C18—C13—C14—C15	−0.1 (3)
C3—N2—C2—C1	−61.3 (3)	C12—C13—C14—C15	−177.89 (18)
N1—C1—C2—N2	83.1 (2)	C13—C14—C15—C16	−0.7 (3)
C2—N2—C3—O1	11.6 (3)	C14—C15—C16—C17	0.8 (3)
C2—N2—C3—C4	−167.04 (19)	C15—C16—C17—C18	−0.3 (3)
O1—C3—C4—C5	−140.5 (2)	C16—C17—C18—C13	−0.5 (3)
N2—C3—C4—C5	38.1 (3)	C14—C13—C18—C17	0.6 (3)
O1—C3—C4—C9	35.0 (3)	C12—C13—C18—C17	178.56 (18)
N2—C3—C4—C9	−146.4 (2)	C10—N1—C19—C20	−166.83 (16)
C9—C4—C5—C6	0.5 (3)	C1—N1—C19—C20	69.6 (2)
C3—C4—C5—C6	175.96 (19)	C21—N4—C20—C19	−140.97 (19)
C4—C5—C6—C7	0.9 (3)	N1—C19—C20—N4	72.5 (2)
C5—C6—C7—C8	−1.0 (3)	C20—N4—C21—O3	6.9 (3)
C6—C7—C8—C9	−0.4 (4)	C20—N4—C21—C22	−170.42 (17)
C7—C8—C9—C4	1.9 (3)	O3—C21—C22—C23	149.1 (2)
C5—C4—C9—C8	−1.9 (3)	N4—C21—C22—C23	−33.5 (3)
C3—C4—C9—C8	−177.53 (19)	O3—C21—C22—C27	−32.3 (3)
C19—N1—C10—C11	75.0 (2)	N4—C21—C22—C27	145.04 (19)
C1—N1—C10—C11	−161.06 (17)	C27—C22—C23—C24	−0.8 (3)
C12—N3—C11—C10	−112.8 (2)	C21—C22—C23—C24	177.74 (19)
N1—C10—C11—N3	58.7 (2)	C22—C23—C24—C25	−1.9 (3)
C11—N3—C12—O2	2.2 (3)	C23—C24—C25—C26	2.3 (3)
C11—N3—C12—C13	−178.72 (17)	C24—C25—C26—C27	−0.1 (3)
O2—C12—C13—C14	148.4 (2)	C25—C26—C27—C22	−2.5 (3)
N3—C12—C13—C14	−30.7 (3)	C23—C22—C27—C26	3.0 (3)
O2—C12—C13—C18	−29.5 (3)	C21—C22—C27—C26	−175.61 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	1.003 (19)	1.70 (2)	2.646 (2)	155.2 (16)
N2—H2N···O3i	0.87 (2)	2.01 (2)	2.861 (2)	168.8 (19)
N3—H3N···F3	0.92 (2)	2.00 (2)	2.901 (2)	170.0 (18)
N4—H4N···O2ii	0.87 (2)	2.12 (2)	2.894 (2)	147.5 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1	1.003 (19)	1.70 (2)	2.646 (2)	155.2 (16)
N2—H2N⋯O3i	0.87 (2)	2.01 (2)	2.861 (2)	168.8 (19)
N3—H3N⋯F3	0.92 (2)	2.00 (2)	2.901 (2)	170.0 (18)
N4—H4N⋯O2ii	0.87 (2)	2.12 (2)	2.894 (2)	147.5 (19)

Symmetry codes: (i) ; (ii) .