rac-(2R,3S)-2-Phenyl-3-(3-phenyl-1,2,3,4-tetra-hydro-quinoxalin-2-yl)quinoxaline.

The title compound, C(28)H(22)N(4), is the unexpected by-product of the reaction of 2-hydroxy-acetophenone and 1,2-diamino-benzene under iodine catalysis, during which a carbon-carbon σ-bond between two quinoxaline units was formed. Although a fully oxidized title compound should sterically be possible, only one quinoxaline ring is fully oxidized while the second ring remains in the reduced form. As expected, the tetra-hydro-quinoxaline unit is not planar; it adopts a sofa conformation, whereby the atom joining the two heterocyclic systems lies out of the plane of the other atoms. The quinoxaline ring system makes a dihedral angle of 53.61 (4)° with its phenyl ring substituent. The crystal packing is determined by pairs of N-H⋯N, N-H⋯π and weak C-H⋯N hydrogen bonds, forming a chain parallel to the a axis.

Related literature

For related literature, see: Banik et al. (1999 ▶); Chen et al. (2005 ▶); Gazit et al. (1996 ▶); Hwang et al. (2005 ▶); Jones et al. (2006 ▶); Kim et al. (2004 ▶); Kulkarni et al. (2006 ▶); McGovern et al. (2005 ▶); More et al. (2005 ▶); Raw et al. (2004 ▶); Robinson & Taylor (2005 ▶); Shirota & Kageyama (2007 ▶).

Experimental

Crystal data

C28H22N4

M = 414.50

Monoclinic,

a = 11.1601 (6) Å

b = 11.3987 (6) Å

c = 16.4638 (8) Å

β = 93.170 (2)°

V = 2091.17 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 133 (2) K

0.35 × 0.35 × 0.32 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: none

24311 measured reflections

6364 independent reflections

3306 reflections with I > 2σ(I)

R int = 0.109

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.152

S = 0.92

6364 reflections

297 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Siemens, 1994 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808015481/su2058sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015481/su2058Isup2.hkl

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

C28H22N4	F000 = 872
Mr = 414.50	Dx = 1.317 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3799 reflections
a = 11.1601 (6) Å	θ = 2–30º
b = 11.3987 (6) Å	µ = 0.08 mm−1
c = 16.4638 (8) Å	T = 133 (2) K
β = 93.170 (2)º	Prism, red
V = 2091.17 (19) Å3	0.35 × 0.35 × 0.32 mm
Z = 4

Bruker SMART 1000 CCD diffractometer	6364 independent reflections
Radiation source: fine-focus sealed tube	3306 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.109
Detector resolution: 8.192 pixels mm-1	θmax = 30.5º
T = 133(2) K	θmin = 1.8º
ω and φ scans	h = −15→15
Absorption correction: none	k = −16→16
24311 measured reflections	l = −23→23

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)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.152	w = 1/[σ2(Fo2) + (0.0734P)2]
S = 0.92	(Δ/σ)max = 0.001
6364 reflections	Δρmax = 0.42 e Å−3
297 parameters	Δρmin = −0.29 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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)7.0105 (0.0062) x + 1.5050 (0.0091) y - 13.1768 (0.0076) z = 0.4647 (0.0095)* -0.0196 (0.0009) N3 * 0.0131 (0.0012) C22 * 0.0135 (0.0011) C17 * -0.0327 (0.0012) N4 * 0.0257 (0.0009) C16 - 0.6550 (0.0023) C15Rms deviation of fitted atoms = 0.02227.1369 (0.0068) x - 0.2689 (0.0093) y + 12.0496 (0.0089) z = 10.3944 (0.0068)Angle to previous plane (with approximate e.s.d.) = 79.01 (0.04)* 0.0027 (0.0013) C23 * -0.0049 (0.0014) C24 * 0.0020 (0.0015) C25 * 0.0031 (0.0014) C26 * -0.0053 (0.0013) C27 * 0.0023 (0.0013) C28Rms deviation of fitted atoms = 0.00365.4792 (0.0064) x + 2.1540 (0.0079) y + 13.5331 (0.0066) z = 12.6941 (0.0020)Angle to previous plane (with approximate e.s.d.) = 15.63 (0.09)* -0.0411 (0.0011) C1 * 0.0366 (0.0011) C2 * 0.0019 (0.0011) N2 * -0.0370 (0.0012) C3 * 0.0330 (0.0012) C8 * 0.0067 (0.0011) N1Rms deviation of fitted atoms = 0.0304- 4.5755 (0.0081) x + 2.1574 (0.0088) y + 15.0404 (0.0054) z = 7.1104 (0.0101)Angle to previous plane (with approximate e.s.d.) = 53.61 (0.04)* -0.0098 (0.0013) C9 * 0.0103 (0.0013) C10 * -0.0010 (0.0014) C11 * -0.0088 (0.0014) C12 * 0.0092 (0.0014) C13 * 0.0001 (0.0013) C14Rms deviation of fitted atoms = 0.0078

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
N1	0.73023 (13)	0.32241 (13)	0.59153 (9)	0.0174 (3)
N2	0.55476 (13)	0.48400 (13)	0.63650 (9)	0.0168 (3)
N3	0.90846 (13)	0.36907 (13)	0.49171 (10)	0.0173 (3)
H01	0.9504 (18)	0.3484 (17)	0.5339 (12)	0.019 (5)*
N4	0.70665 (15)	0.39968 (13)	0.38883 (10)	0.0187 (4)
H02	0.639 (2)	0.408 (2)	0.3641 (15)	0.043 (7)*
C1	0.73376 (15)	0.43303 (15)	0.56896 (10)	0.0147 (4)
C2	0.64804 (15)	0.51743 (15)	0.59598 (10)	0.0158 (4)
C3	0.54617 (16)	0.36728 (15)	0.65568 (10)	0.0157 (4)
C4	0.44601 (16)	0.32623 (17)	0.69629 (10)	0.0191 (4)
H4	0.3847	0.3792	0.7103	0.023*
C5	0.43791 (18)	0.20925 (17)	0.71539 (11)	0.0228 (4)
H5	0.3694	0.1811	0.7411	0.027*
C6	0.53032 (18)	0.13035 (17)	0.69726 (11)	0.0239 (4)
H6	0.5238	0.0498	0.7113	0.029*
C7	0.62894 (18)	0.16901 (17)	0.65979 (11)	0.0225 (4)
H7	0.6919	0.1160	0.6493	0.027*
C8	0.63732 (17)	0.28797 (16)	0.63657 (10)	0.0173 (4)
C9	0.66016 (16)	0.64540 (15)	0.58036 (11)	0.0174 (4)
C10	0.56469 (17)	0.70799 (16)	0.54368 (11)	0.0205 (4)
H10	0.4918	0.6686	0.5286	0.025*
C11	0.57501 (19)	0.82717 (17)	0.52897 (12)	0.0270 (5)
H11	0.5099	0.8690	0.5030	0.032*
C12	0.6806 (2)	0.88530 (18)	0.55223 (13)	0.0305 (5)
H12	0.6881	0.9668	0.5416	0.037*
C13	0.77457 (19)	0.82530 (17)	0.59063 (13)	0.0280 (5)
H13	0.8459	0.8659	0.6077	0.034*
C14	0.76546 (17)	0.70532 (17)	0.60446 (12)	0.0229 (4)
H14	0.8309	0.6640	0.6303	0.027*
C15	0.82767 (15)	0.46513 (15)	0.50791 (11)	0.0161 (4)
H15	0.8761	0.5330	0.5299	0.019*
C16	0.76314 (16)	0.50187 (15)	0.42612 (11)	0.0170 (4)
H16	0.6983	0.5586	0.4385	0.020*
C17	0.75484 (15)	0.28781 (15)	0.39818 (11)	0.0154 (4)
C18	0.70330 (17)	0.19060 (16)	0.35817 (11)	0.0204 (4)
H18	0.6338	0.2006	0.3229	0.025*
C19	0.75227 (18)	0.07975 (17)	0.36928 (12)	0.0254 (5)
H19	0.7159	0.0143	0.3420	0.030*
C20	0.85415 (18)	0.06402 (17)	0.42005 (12)	0.0262 (5)
H20	0.8884	−0.0118	0.4272	0.031*
C21	0.90571 (17)	0.15974 (17)	0.46026 (11)	0.0226 (4)
H21	0.9756	0.1487	0.4950	0.027*
C22	0.85742 (15)	0.27129 (15)	0.45090 (10)	0.0157 (4)
C23	0.84954 (16)	0.56456 (16)	0.37228 (10)	0.0166 (4)
C24	0.92716 (18)	0.50358 (18)	0.32431 (12)	0.0261 (5)
H24	0.9247	0.4203	0.3231	0.031*
C25	1.00828 (19)	0.56274 (18)	0.27815 (12)	0.0300 (5)
H25	1.0612	0.5195	0.2462	0.036*
C26	1.01289 (18)	0.68356 (18)	0.27821 (12)	0.0279 (5)
H26	1.0687	0.7236	0.2466	0.033*
C27	0.93552 (18)	0.74584 (18)	0.32474 (12)	0.0263 (5)
H27	0.9373	0.8292	0.3246	0.032*
C28	0.85472 (17)	0.68660 (16)	0.37190 (11)	0.0207 (4)
H28	0.8026	0.7302	0.4042	0.025*

	U11	U22	U33	U12	U13	U23
N1	0.0193 (8)	0.0180 (8)	0.0151 (8)	−0.0017 (6)	0.0013 (6)	−0.0004 (6)
N2	0.0183 (8)	0.0170 (8)	0.0151 (7)	−0.0004 (6)	0.0007 (6)	0.0009 (6)
N3	0.0133 (8)	0.0209 (8)	0.0176 (8)	0.0021 (6)	−0.0016 (6)	0.0006 (7)
N4	0.0156 (8)	0.0164 (8)	0.0234 (9)	0.0010 (6)	−0.0053 (7)	0.0001 (6)
C1	0.0146 (9)	0.0171 (9)	0.0122 (8)	0.0002 (7)	−0.0019 (7)	−0.0019 (7)
C2	0.0153 (9)	0.0177 (9)	0.0141 (9)	−0.0007 (7)	−0.0024 (7)	0.0001 (7)
C3	0.0164 (9)	0.0160 (9)	0.0144 (9)	−0.0005 (7)	−0.0017 (7)	0.0007 (7)
C4	0.0176 (9)	0.0245 (10)	0.0151 (9)	−0.0013 (8)	0.0009 (7)	0.0018 (8)
C5	0.0251 (11)	0.0251 (11)	0.0182 (10)	−0.0085 (8)	0.0008 (8)	0.0049 (8)
C6	0.0350 (11)	0.0190 (10)	0.0177 (10)	−0.0048 (9)	0.0002 (8)	0.0033 (8)
C7	0.0275 (11)	0.0199 (10)	0.0200 (10)	0.0014 (8)	0.0013 (8)	0.0005 (8)
C8	0.0211 (9)	0.0192 (9)	0.0115 (8)	−0.0020 (7)	−0.0001 (7)	0.0008 (7)
C9	0.0198 (9)	0.0179 (9)	0.0150 (9)	−0.0004 (7)	0.0047 (7)	−0.0003 (7)
C10	0.0222 (10)	0.0198 (10)	0.0196 (9)	−0.0014 (8)	0.0016 (8)	−0.0004 (8)
C11	0.0371 (12)	0.0182 (10)	0.0260 (11)	0.0032 (9)	0.0039 (9)	0.0009 (8)
C12	0.0445 (13)	0.0159 (10)	0.0322 (12)	−0.0033 (9)	0.0117 (10)	−0.0005 (9)
C13	0.0296 (11)	0.0207 (11)	0.0345 (12)	−0.0098 (9)	0.0089 (9)	−0.0085 (9)
C14	0.0192 (10)	0.0218 (10)	0.0277 (11)	−0.0009 (8)	0.0015 (8)	−0.0040 (8)
C15	0.0147 (9)	0.0168 (9)	0.0170 (9)	0.0002 (7)	0.0016 (7)	−0.0012 (7)
C16	0.0163 (9)	0.0169 (9)	0.0178 (9)	−0.0006 (7)	0.0010 (7)	−0.0025 (7)
C17	0.0157 (9)	0.0155 (9)	0.0152 (9)	−0.0007 (7)	0.0041 (7)	0.0009 (7)
C18	0.0230 (10)	0.0226 (10)	0.0158 (9)	−0.0028 (8)	0.0019 (8)	−0.0007 (8)
C19	0.0339 (12)	0.0174 (10)	0.0253 (11)	−0.0042 (9)	0.0057 (9)	−0.0035 (8)
C20	0.0335 (12)	0.0201 (10)	0.0258 (11)	0.0075 (9)	0.0081 (9)	0.0021 (8)
C21	0.0206 (10)	0.0252 (11)	0.0223 (10)	0.0079 (8)	0.0036 (8)	0.0021 (8)
C22	0.0141 (9)	0.0183 (9)	0.0151 (9)	0.0000 (7)	0.0040 (7)	0.0004 (7)
C23	0.0178 (9)	0.0180 (9)	0.0139 (9)	−0.0001 (7)	−0.0004 (7)	0.0019 (7)
C24	0.0328 (12)	0.0214 (10)	0.0249 (11)	−0.0028 (9)	0.0091 (9)	−0.0006 (8)
C25	0.0378 (13)	0.0285 (12)	0.0250 (11)	0.0005 (10)	0.0137 (9)	0.0007 (9)
C26	0.0279 (11)	0.0299 (12)	0.0264 (11)	−0.0059 (9)	0.0059 (9)	0.0075 (9)
C27	0.0315 (12)	0.0212 (11)	0.0259 (11)	−0.0033 (9)	−0.0010 (9)	0.0054 (8)
C28	0.0225 (10)	0.0197 (10)	0.0200 (9)	0.0026 (8)	0.0006 (8)	0.0007 (8)

N1—C1	1.316 (2)	C21—C22	1.386 (3)
N1—C8	1.365 (2)	C23—C24	1.390 (3)
N2—C2	1.323 (2)	C23—C28	1.392 (3)
N2—C3	1.372 (2)	C24—C25	1.389 (3)
N3—C22	1.406 (2)	C25—C26	1.378 (3)
N3—C15	1.453 (2)	C26—C27	1.382 (3)
N4—C17	1.389 (2)	C27—C28	1.396 (3)
N4—C16	1.445 (2)	N3—H01	0.85 (2)
C1—C2	1.444 (2)	N4—H02	0.84 (2)
C1—C15	1.536 (2)	C4—H4	0.9500
C2—C9	1.489 (2)	C5—H5	0.9500
C3—C8	1.409 (2)	C6—H6	0.9500
C3—C4	1.414 (2)	C7—H7	0.9500
C4—C5	1.374 (3)	C10—H10	0.9500
C5—C6	1.413 (3)	C11—H11	0.9500
C6—C7	1.364 (3)	C12—H12	0.9500
C7—C8	1.413 (3)	C13—H13	0.9500
C9—C10	1.392 (3)	C14—H14	0.9500
C9—C14	1.398 (3)	C15—H15	1.0000
C10—C11	1.386 (3)	C16—H16	1.0000
C11—C12	1.387 (3)	C18—H18	0.9500
C12—C13	1.376 (3)	C19—H19	0.9500
C13—C14	1.391 (3)	C20—H20	0.9500
C15—C16	1.549 (2)	C21—H21	0.9500
C16—C23	1.523 (2)	C24—H24	0.9500
C17—C18	1.397 (3)	C25—H25	0.9500
C17—C22	1.411 (2)	C26—H26	0.9500
C18—C19	1.385 (3)	C27—H27	0.9500
C19—C20	1.385 (3)	C28—H28	0.9500
C20—C21	1.385 (3)
C1—N1—C8	117.67 (15)	C25—C26—C27	119.30 (19)
C2—N2—C3	117.53 (15)	C26—C27—C28	120.16 (18)
C22—N3—C15	116.50 (15)	C23—C28—C27	120.93 (18)
C17—N4—C16	122.39 (15)	C22—N3—H01	111.2 (13)
N1—C1—C2	121.38 (16)	C15—N3—H01	112.2 (13)
N1—C1—C15	116.44 (15)	C17—N4—H02	119.4 (16)
C2—C1—C15	122.04 (15)	C16—N4—H02	118.0 (16)
N2—C2—C1	121.10 (16)	C5—C4—H4	120.2
N2—C2—C9	116.80 (15)	C3—C4—H4	120.2
C1—C2—C9	122.10 (16)	C4—C5—H5	119.6
N2—C3—C8	120.67 (16)	C6—C5—H5	119.6
N2—C3—C4	119.80 (16)	C7—C6—H6	119.8
C8—C3—C4	119.52 (16)	C5—C6—H6	119.8
C5—C4—C3	119.55 (17)	C6—C7—H7	120.0
C4—C5—C6	120.76 (17)	C8—C7—H7	120.0
C7—C6—C5	120.43 (18)	C11—C10—H10	119.7
C6—C7—C8	119.95 (18)	C9—C10—H10	119.7
N1—C8—C3	121.07 (16)	C10—C11—H11	120.1
N1—C8—C7	119.10 (17)	C12—C11—H11	120.1
C3—C8—C7	119.71 (17)	C13—C12—H12	119.9
C10—C9—C14	118.95 (17)	C11—C12—H12	119.9
C10—C9—C2	120.16 (16)	C12—C13—H13	119.9
C14—C9—C2	120.86 (16)	C14—C13—H13	119.9
C11—C10—C9	120.61 (18)	C13—C14—H14	119.9
C10—C11—C12	119.83 (19)	C9—C14—H14	119.9
C13—C12—C11	120.24 (19)	N3—C15—H15	108.8
C12—C13—C14	120.20 (19)	C1—C15—H15	108.8
C13—C14—C9	120.13 (18)	C16—C15—H15	108.8
N3—C15—C1	113.18 (14)	N4—C16—H16	107.7
N3—C15—C16	107.91 (14)	C23—C16—H16	107.7
C1—C15—C16	109.39 (14)	C15—C16—H16	107.7
N4—C16—C23	113.96 (15)	C19—C18—H18	119.6
N4—C16—C15	108.80 (14)	C17—C18—H18	119.6
C23—C16—C15	110.72 (14)	C18—C19—H19	119.9
N4—C17—C18	121.95 (16)	C20—C19—H19	119.9
N4—C17—C22	119.13 (16)	C21—C20—H20	120.3
C18—C17—C22	118.91 (16)	C19—C20—H20	120.3
C19—C18—C17	120.83 (18)	C20—C21—H21	119.3
C18—C19—C20	120.17 (18)	C22—C21—H21	119.3
C21—C20—C19	119.48 (18)	C25—C24—H24	119.5
C20—C21—C22	121.39 (18)	C23—C24—H24	119.5
C21—C22—N3	121.97 (17)	C26—C25—H25	119.7
C21—C22—C17	119.21 (17)	C24—C25—H25	119.7
N3—C22—C17	118.81 (16)	C25—C26—H26	120.3
C24—C23—C28	118.01 (17)	C27—C26—H26	120.3
C24—C23—C16	122.03 (16)	C26—C27—H27	119.9
C28—C23—C16	119.94 (16)	C28—C27—H27	119.9
C25—C24—C23	120.91 (18)	C23—C28—H28	119.5
C26—C25—C24	120.69 (19)	C27—C28—H28	119.5
C8—N1—C1—C2	4.7 (2)	N1—C1—C15—N3	−6.8 (2)
C8—N1—C1—C15	−171.04 (15)	C2—C1—C15—N3	177.41 (15)
C3—N2—C2—C1	3.5 (2)	N1—C1—C15—C16	113.51 (17)
C3—N2—C2—C9	−176.16 (15)	C2—C1—C15—C16	−62.2 (2)
N1—C1—C2—N2	−8.0 (3)	C17—N4—C16—C23	91.8 (2)
C15—C1—C2—N2	167.59 (16)	C17—N4—C16—C15	−32.3 (2)
N1—C1—C2—C9	171.65 (16)	N3—C15—C16—N4	54.42 (18)
C15—C1—C2—C9	−12.8 (2)	C1—C15—C16—N4	−69.11 (18)
C2—N2—C3—C8	3.4 (2)	N3—C15—C16—C23	−71.57 (18)
C2—N2—C3—C4	−177.68 (16)	C1—C15—C16—C23	164.91 (14)
N2—C3—C4—C5	−179.96 (16)	C16—N4—C17—C18	−176.29 (16)
C8—C3—C4—C5	−1.1 (3)	C16—N4—C17—C22	5.0 (3)
C3—C4—C5—C6	2.1 (3)	N4—C17—C18—C19	−179.23 (17)
C4—C5—C6—C7	−0.5 (3)	C22—C17—C18—C19	−0.6 (3)
C5—C6—C7—C8	−2.0 (3)	C17—C18—C19—C20	−0.5 (3)
C1—N1—C8—C3	2.2 (2)	C18—C19—C20—C21	0.7 (3)
C1—N1—C8—C7	178.17 (16)	C19—C20—C21—C22	0.1 (3)
N2—C3—C8—N1	−6.6 (3)	C20—C21—C22—N3	179.64 (17)
C4—C3—C8—N1	174.52 (16)	C20—C21—C22—C17	−1.1 (3)
N2—C3—C8—C7	177.48 (16)	C15—N3—C22—C21	−152.96 (17)
C4—C3—C8—C7	−1.4 (3)	C15—N3—C22—C17	27.8 (2)
C6—C7—C8—N1	−173.07 (17)	N4—C17—C22—C21	−179.94 (16)
C6—C7—C8—C3	2.9 (3)	C18—C17—C22—C21	1.3 (3)
N2—C2—C9—C10	−53.0 (2)	N4—C17—C22—N3	−0.7 (2)
C1—C2—C9—C10	127.41 (18)	C18—C17—C22—N3	−179.40 (16)
N2—C2—C9—C14	124.95 (19)	N4—C16—C23—C24	−40.5 (2)
C1—C2—C9—C14	−54.7 (2)	C15—C16—C23—C24	82.5 (2)
C14—C9—C10—C11	2.0 (3)	N4—C16—C23—C28	141.30 (17)
C2—C9—C10—C11	179.92 (17)	C15—C16—C23—C28	−95.7 (2)
C9—C10—C11—C12	−1.1 (3)	C28—C23—C24—C25	0.7 (3)
C10—C11—C12—C13	−0.7 (3)	C16—C23—C24—C25	−177.50 (18)
C11—C12—C13—C14	1.7 (3)	C23—C24—C25—C26	−0.7 (3)
C12—C13—C14—C9	−0.8 (3)	C24—C25—C26—C27	−0.1 (3)
C10—C9—C14—C13	−1.0 (3)	C25—C26—C27—C28	0.8 (3)
C2—C9—C14—C13	−178.92 (17)	C24—C23—C28—C27	0.0 (3)
C22—N3—C15—C1	66.7 (2)	C16—C23—C28—C27	178.24 (16)
C22—N3—C15—C16	−54.46 (19)	C26—C27—C28—C23	−0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H02···N2i	0.84 (2)	2.49 (2)	3.211 (2)	144 (2)
C15—H15···N3ii	1.00	2.69	3.499 (2)	138
N3—H01···Cent(C23–C28)ii	0.85 (2)	2.63	3.42	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H02⋯N2i	0.84 (2)	2.49 (2)	3.211 (2)	144 (2)
C15—H15⋯N3ii	1.00	2.69	3.499 (2)	138
N3—H01⋯Cent(C23–C28)ii	0.85 (2)	2.63	3.42	157

Symmetry codes: (i) ; (ii) .