N-{2-[(4S)-4-tert-Butyl-4,5-dihydro-1,3-oxazol-2-yl]phen-yl}-5,6-diphenyl-1,2,4-triazin-3-amine.

The title compound, C(28)H(27)N(5)O, was synthesized using palladium cross-coupling amination of 3-bromo-5,6-diphenyl-1,2,4-triazine with 2-[(4S)-4-tert-butyl-4,5-dihydro-1,3-oxazol-2-yl]aniline. The oxazoline ring is almost planar, with a maximum atomic deviation of 0.023 (5) Å. The phenyl rings make dihedral angles of 29.0 (1) and 54.6 (1)° with the triazine ring while the benzene ring makes a dihedral angle of 0.6 (1)° with the oxazoline ring. The conformation of the mol-ecule is influenced by strong intra-molecular N-H⋯N and weak C-H⋯N hydrogen bonds. In the crystal, screw-axis related mol-ecules are linked into supra-molecular chains by inter-molecular C-H⋯O hydrogen bonds. π-π stacking is observed between the oxazoline and triazine rings of adjacent mol-ecules, with a centroid-centroid distance of 3.749 (2) Å.

Related literature

For applications of compounds containing a chiral oxazoline ring in asymmetric catalysis, see: Lindsey & Layton (2004 ▶); Desimoni et al. (2006 ▶); Hargaden & Guiry (2009 ▶). For related structures, see: Castro et al. (2001 ▶); Coeffard et al. (2009 ▶).

Experimental

Crystal data

C28H27N5O

M = 449.55

Orthorhombic,

a = 6.3306 (2) Å

b = 16.9244 (6) Å

c = 22.5787 (8) Å

V = 2419.12 (14) Å3

Z = 4

Cu Kα radiation

μ = 0.61 mm−1

T = 293 K

0.54 × 0.02 × 0.02 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.882, T max = 1.000

28527 measured reflections

2625 independent reflections

1648 reflections with I > 2σ(I)

R int = 0.090

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.134

S = 1.05

2625 reflections

311 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811005411/xu5158sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005411/xu5158Isup2.hkl

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

C28H27N5O	Dx = 1.234 Mg m−3
Mr = 449.55	Melting point = 489–490 K
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1210 reflections
a = 6.3306 (2) Å	θ = 4.6–30.0°
b = 16.9244 (6) Å	µ = 0.61 mm−1
c = 22.5787 (8) Å	T = 293 K
V = 2419.12 (14) Å3	Needle, yellow
Z = 4	0.54 × 0.02 × 0.02 mm
F(000) = 952

Bruker SMART APEXII CCD diffractometer	2625 independent reflections
Radiation source: fine-focus sealed tube	1648 reflections with I > 2σ(I)
graphite	Rint = 0.090
ω scans	θmax = 70.2°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→6
Tmin = 0.882, Tmax = 1.000	k = −20→20
28527 measured reflections	l = −27→27

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.134	w = 1/[σ2(Fo2) + (0.0683P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2625 reflections	Δρmax = 0.15 e Å−3
311 parameters	Δρmin = −0.17 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: 0.0053 (5)

Experimental. 1H NMR (400 MHz, CDCl3) δ: 1.05 (s, 9H, (CH3)3C), 4.25–4.35 (m, 2H, (CH2O and CHN), 4.45–4.50 (m, 1H, CH2O), 7.11 (t, 1H, J = 7.6 Hz, Ph), 7.31–7.37 (m, 5H, Ph), 7.42–7.44 (m, 1H, Ph), 7.50–7.52 (m, 2H, Ph), 7.56–7.60 (m, 3H, Ph), 7.91 (d, 1H, J = 7.6 Hz, Ph), 8.89 (d, 1H, J = 8.4 Hz, Ph), 12.98 (s, 1H, NH); 13C NMR (50 MHz, CDCl3) δ: 25.9, 34.0, 67.5, 76.1, 112.8, 118.9, 120.7, 128.2, 128.3, 128.6, 129.2, 129.3, 129.8, 130.4, 132.3, 136.0, 136.1, 140.8, 150.8, 156.0, 158.8, 163.4; Analysis calculated for C28H27N5O: C 74.81; H 6.05; N 15.58; found: C 74.79; H 6.03; N 15.51.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 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
O18	0.9330 (4)	0.61773 (16)	0.78505 (12)	0.0793 (8)
N1	−0.0592 (5)	0.54476 (19)	0.97426 (12)	0.0735 (9)
N2	0.0979 (5)	0.58502 (18)	0.94731 (14)	0.0728 (9)
N4	0.1210 (5)	0.48257 (17)	0.87487 (12)	0.0640 (8)
N7	0.3575 (5)	0.58275 (18)	0.87252 (13)	0.0697 (9)
H7	0.411 (8)	0.548 (2)	0.8420 (18)	0.105*
N15	0.6459 (5)	0.54077 (19)	0.79214 (13)	0.0716 (9)
C3	0.1856 (6)	0.5505 (2)	0.90057 (16)	0.0611 (9)
C5	−0.0365 (6)	0.4448 (2)	0.90072 (15)	0.0578 (9)
C6	−0.1237 (6)	0.4751 (2)	0.95379 (15)	0.0613 (9)
C8	0.4787 (6)	0.6496 (2)	0.88589 (15)	0.0647 (10)
C9	0.6707 (6)	0.6585 (2)	0.85444 (16)	0.0637 (10)
C10	0.7987 (7)	0.7239 (2)	0.86881 (17)	0.0784 (11)
H10	0.9268	0.7306	0.8493	0.118*
C11	0.7389 (8)	0.7781 (3)	0.91095 (19)	0.0894 (14)
H11	0.8266	0.8205	0.9200	0.134*
C12	0.5491 (8)	0.7693 (2)	0.93957 (18)	0.0828 (12)
H12	0.5080	0.8064	0.9677	0.124*
C13	0.4183 (8)	0.7061 (2)	0.92720 (16)	0.0780 (12)
H13	0.2893	0.7014	0.9466	0.117*
C14	0.7399 (6)	0.6022 (2)	0.80992 (16)	0.0647 (10)
C16	0.7797 (6)	0.5003 (2)	0.74766 (16)	0.0668 (10)
H16	0.8305	0.4509	0.7653	0.100*
C17	0.9690 (7)	0.5565 (3)	0.74209 (19)	0.0855 (12)
H171	1.0999	0.5289	0.7504	0.128*
H172	0.9764	0.5786	0.7025	0.128*
C19	0.6617 (6)	0.4794 (2)	0.69076 (17)	0.0741 (11)
C20	0.4820 (8)	0.4227 (3)	0.7063 (2)	0.1036 (15)
H201	0.3925	0.4466	0.7357	0.155*
H202	0.5398	0.3744	0.7217	0.155*
H203	0.4007	0.4115	0.6714	0.155*
C21	0.8171 (9)	0.4373 (3)	0.64968 (19)	0.1075 (16)
H211	0.8815	0.3940	0.6704	0.161*
H212	0.9243	0.4737	0.6371	0.161*
H213	0.7429	0.4176	0.6157	0.161*
C22	0.5743 (10)	0.5535 (3)	0.6608 (2)	0.1179 (18)
H221	0.6884	0.5888	0.6516	0.177*
H222	0.4769	0.5793	0.6870	0.177*
H223	0.5026	0.5389	0.6250	0.177*
C51	−0.1113 (6)	0.3731 (2)	0.86873 (14)	0.0588 (9)
C52	0.0351 (7)	0.3342 (2)	0.83248 (16)	0.0694 (11)
H52	0.1747	0.3513	0.8317	0.104*
C53	−0.0247 (7)	0.2709 (2)	0.7979 (2)	0.0833 (12)
H53	0.0742	0.2456	0.7741	0.125*
C54	−0.2320 (7)	0.2451 (2)	0.7986 (2)	0.0828 (12)
H54	−0.2729	0.2026	0.7751	0.124*
C55	−0.3780 (7)	0.2826 (2)	0.83435 (18)	0.0802 (12)
H55	−0.5171	0.2650	0.8351	0.120*
C56	−0.3186 (6)	0.3463 (2)	0.86901 (16)	0.0684 (10)
H56	−0.4184	0.3713	0.8927	0.103*
C61	−0.2858 (6)	0.4352 (2)	0.99015 (15)	0.0676 (10)
C62	−0.2523 (8)	0.3591 (2)	1.01024 (18)	0.0882 (13)
H62	−0.1272	0.3328	1.0013	0.132*
C63	−0.4080 (12)	0.3219 (4)	1.0441 (2)	0.119 (2)
H63	−0.3863	0.2707	1.0579	0.179*
C64	−0.5935 (11)	0.3607 (5)	1.0572 (2)	0.133 (3)
H64	−0.6972	0.3355	1.0794	0.200*
C65	−0.6258 (9)	0.4369 (4)	1.0375 (2)	0.1133 (19)
H65	−0.7513	0.4631	1.0460	0.170*
C66	−0.4700 (6)	0.4739 (3)	1.00486 (17)	0.0838 (13)
H66	−0.4897	0.5258	0.9926	0.126*

	U11	U22	U33	U12	U13	U23
O18	0.0671 (17)	0.0869 (18)	0.0839 (17)	−0.0114 (14)	0.0118 (14)	0.0045 (16)
N1	0.079 (2)	0.074 (2)	0.068 (2)	−0.0071 (18)	0.0151 (17)	−0.0099 (17)
N2	0.078 (2)	0.072 (2)	0.0678 (19)	−0.0101 (17)	0.0166 (17)	−0.0130 (17)
N4	0.0636 (19)	0.0691 (19)	0.0592 (17)	−0.0067 (16)	0.0089 (15)	−0.0032 (15)
N7	0.072 (2)	0.070 (2)	0.067 (2)	−0.0153 (17)	0.0156 (17)	−0.0113 (16)
N15	0.074 (2)	0.073 (2)	0.0673 (19)	−0.0073 (18)	0.0152 (17)	−0.0071 (17)
C3	0.062 (2)	0.063 (2)	0.058 (2)	−0.0057 (19)	0.0050 (18)	−0.0041 (19)
C5	0.059 (2)	0.060 (2)	0.054 (2)	0.0002 (18)	0.0035 (17)	0.0006 (17)
C6	0.066 (2)	0.067 (2)	0.051 (2)	−0.0009 (19)	0.0042 (18)	−0.0020 (18)
C8	0.072 (2)	0.064 (2)	0.058 (2)	−0.007 (2)	0.0023 (19)	0.0023 (19)
C9	0.066 (2)	0.065 (2)	0.059 (2)	−0.0057 (19)	−0.0018 (18)	0.0071 (19)
C10	0.080 (3)	0.078 (3)	0.076 (3)	−0.022 (2)	−0.002 (2)	0.009 (2)
C11	0.110 (4)	0.078 (3)	0.080 (3)	−0.026 (3)	−0.009 (3)	−0.005 (2)
C12	0.103 (3)	0.074 (3)	0.071 (3)	−0.013 (3)	0.001 (3)	−0.012 (2)
C13	0.093 (3)	0.075 (3)	0.066 (2)	−0.013 (2)	0.003 (2)	−0.014 (2)
C14	0.059 (2)	0.073 (2)	0.061 (2)	−0.007 (2)	0.0077 (19)	0.009 (2)
C16	0.066 (2)	0.074 (2)	0.061 (2)	0.0077 (19)	0.0127 (19)	0.0087 (19)
C17	0.075 (3)	0.101 (3)	0.080 (3)	−0.005 (3)	0.014 (2)	−0.003 (3)
C19	0.078 (3)	0.079 (3)	0.065 (2)	0.008 (2)	0.003 (2)	0.001 (2)
C20	0.095 (3)	0.108 (4)	0.108 (3)	−0.017 (3)	0.008 (3)	−0.024 (3)
C21	0.109 (4)	0.136 (4)	0.077 (3)	0.014 (3)	0.023 (3)	−0.016 (3)
C22	0.123 (4)	0.128 (4)	0.103 (4)	0.032 (4)	−0.023 (3)	0.025 (3)
C51	0.065 (2)	0.056 (2)	0.056 (2)	−0.0021 (18)	−0.0004 (18)	−0.0003 (17)
C52	0.071 (3)	0.063 (2)	0.075 (3)	0.002 (2)	0.006 (2)	−0.008 (2)
C53	0.086 (3)	0.070 (3)	0.094 (3)	0.003 (2)	0.010 (3)	−0.018 (2)
C54	0.088 (3)	0.072 (3)	0.088 (3)	−0.004 (2)	−0.008 (3)	−0.017 (2)
C55	0.076 (3)	0.073 (3)	0.092 (3)	−0.006 (2)	−0.008 (2)	−0.014 (2)
C56	0.064 (2)	0.073 (2)	0.068 (2)	−0.004 (2)	0.0008 (19)	−0.002 (2)
C61	0.072 (3)	0.080 (3)	0.051 (2)	−0.015 (2)	0.0057 (18)	0.000 (2)
C62	0.110 (4)	0.088 (3)	0.067 (2)	−0.022 (3)	0.003 (2)	0.008 (2)
C63	0.159 (6)	0.117 (4)	0.081 (3)	−0.054 (4)	−0.001 (4)	0.020 (3)
C64	0.126 (5)	0.199 (7)	0.075 (3)	−0.074 (6)	0.013 (4)	0.007 (4)
C65	0.086 (4)	0.180 (6)	0.074 (3)	−0.032 (4)	0.015 (3)	−0.001 (4)
C66	0.065 (3)	0.125 (4)	0.062 (2)	−0.011 (3)	0.009 (2)	−0.005 (2)

O18—C14	1.370 (4)	C19—C21	1.529 (6)
O18—C17	1.437 (5)	C20—H201	0.9600
N1—C6	1.330 (4)	C20—H202	0.9600
N1—N2	1.351 (4)	C20—H203	0.9600
N2—C3	1.328 (4)	C21—H211	0.9600
N4—C5	1.320 (4)	C21—H212	0.9600
N4—C3	1.351 (4)	C21—H213	0.9600
N7—C3	1.372 (4)	C22—H221	0.9600
N7—C8	1.399 (4)	C22—H222	0.9600
N7—H7	0.97 (4)	C22—H223	0.9600
N15—C14	1.264 (5)	C51—C56	1.389 (5)
N15—C16	1.482 (5)	C51—C52	1.401 (5)
C5—C6	1.415 (5)	C52—C53	1.379 (5)
C5—C51	1.490 (5)	C52—H52	0.9300
C6—C61	1.478 (5)	C53—C54	1.383 (6)
C8—C13	1.390 (5)	C53—H53	0.9300
C8—C9	1.416 (5)	C54—C55	1.382 (6)
C9—C10	1.410 (5)	C54—H54	0.9300
C9—C14	1.452 (5)	C55—C56	1.383 (5)
C10—C11	1.375 (6)	C55—H55	0.9300
C10—H10	0.9300	C56—H56	0.9300
C11—C12	1.372 (6)	C61—C66	1.377 (5)
C11—H11	0.9300	C61—C62	1.382 (5)
C12—C13	1.381 (6)	C62—C63	1.397 (7)
C12—H12	0.9300	C62—H62	0.9300
C13—H13	0.9300	C63—C64	1.378 (9)
C16—C19	1.527 (5)	C63—H63	0.9300
C16—C17	1.536 (6)	C64—C65	1.380 (8)
C16—H16	0.9800	C64—H64	0.9300
C17—H171	0.9700	C65—C66	1.381 (6)
C17—H172	0.9700	C65—H65	0.9300
C19—C22	1.528 (5)	C66—H66	0.9300
C19—C20	1.530 (6)
C14—O18—C17	106.3 (3)	C20—C19—C21	109.0 (3)
C6—N1—N2	121.1 (3)	C19—C20—H201	109.5
C3—N2—N1	116.3 (3)	C19—C20—H202	109.5
C5—N4—C3	116.8 (3)	H201—C20—H202	109.5
C3—N7—C8	131.1 (3)	C19—C20—H203	109.5
C3—N7—H7	111 (3)	H201—C20—H203	109.5
C8—N7—H7	117 (3)	H202—C20—H203	109.5
C14—N15—C16	109.1 (3)	C19—C21—H211	109.5
N2—C3—N4	126.1 (3)	C19—C21—H212	109.5
N2—C3—N7	121.5 (3)	H211—C21—H212	109.5
N4—C3—N7	112.4 (3)	C19—C21—H213	109.5
N4—C5—C6	119.6 (3)	H211—C21—H213	109.5
N4—C5—C51	114.8 (3)	H212—C21—H213	109.5
C6—C5—C51	125.6 (3)	C19—C22—H221	109.5
N1—C6—C5	119.7 (3)	C19—C22—H222	109.5
N1—C6—C61	115.2 (3)	H221—C22—H222	109.5
C5—C6—C61	125.1 (3)	C19—C22—H223	109.5
C13—C8—N7	123.4 (3)	H221—C22—H223	109.5
C13—C8—C9	119.9 (3)	H222—C22—H223	109.5
N7—C8—C9	116.7 (3)	C56—C51—C52	118.3 (3)
C10—C9—C8	117.5 (4)	C56—C51—C5	124.4 (3)
C10—C9—C14	120.0 (4)	C52—C51—C5	117.1 (3)
C8—C9—C14	122.4 (3)	C53—C52—C51	120.9 (4)
C11—C10—C9	121.7 (4)	C53—C52—H52	119.5
C11—C10—H10	119.2	C51—C52—H52	119.5
C9—C10—H10	119.2	C52—C53—C54	120.0 (4)
C10—C11—C12	119.6 (4)	C52—C53—H53	120.0
C10—C11—H11	120.2	C54—C53—H53	120.0
C12—C11—H11	120.2	C53—C54—C55	119.7 (4)
C11—C12—C13	121.0 (4)	C53—C54—H54	120.1
C11—C12—H12	119.5	C55—C54—H54	120.1
C13—C12—H12	119.5	C54—C55—C56	120.4 (4)
C12—C13—C8	120.3 (4)	C54—C55—H55	119.8
C12—C13—H13	119.9	C56—C55—H55	119.8
C8—C13—H13	119.9	C55—C56—C51	120.6 (4)
N15—C14—O18	116.6 (4)	C55—C56—H56	119.7
N15—C14—C9	128.1 (3)	C51—C56—H56	119.7
O18—C14—C9	115.3 (3)	C66—C61—C62	119.6 (4)
N15—C16—C19	113.4 (3)	C66—C61—C6	120.3 (4)
N15—C16—C17	102.4 (3)	C62—C61—C6	120.1 (4)
C19—C16—C17	117.1 (3)	C61—C62—C63	119.4 (5)
N15—C16—H16	107.8	C61—C62—H62	120.3
C19—C16—H16	107.8	C63—C62—H62	120.3
C17—C16—H16	107.8	C64—C63—C62	120.2 (6)
O18—C17—C16	105.5 (3)	C64—C63—H63	119.9
O18—C17—H171	110.6	C62—C63—H63	119.9
C16—C17—H171	110.6	C65—C64—C63	120.2 (6)
O18—C17—H172	110.6	C65—C64—H64	119.9
C16—C17—H172	110.6	C63—C64—H64	119.9
H171—C17—H172	108.8	C64—C65—C66	119.3 (6)
C16—C19—C22	111.1 (3)	C64—C65—H65	120.3
C16—C19—C20	108.4 (3)	C66—C65—H65	120.3
C22—C19—C20	110.3 (4)	C61—C66—C65	121.2 (5)
C16—C19—C21	107.7 (3)	C61—C66—H66	119.4
C22—C19—C21	110.3 (4)	C65—C66—H66	119.4
C6—N1—N2—C3	−1.4 (5)	C14—N15—C16—C19	−130.0 (4)
N1—N2—C3—N4	5.9 (6)	C14—N15—C16—C17	−2.9 (4)
N1—N2—C3—N7	−174.7 (3)	C14—O18—C17—C16	−3.5 (4)
C5—N4—C3—N2	−4.1 (5)	N15—C16—C17—O18	3.8 (4)
C5—N4—C3—N7	176.4 (3)	C19—C16—C17—O18	128.6 (4)
C8—N7—C3—N2	3.9 (6)	N15—C16—C19—C22	59.9 (5)
C8—N7—C3—N4	−176.7 (3)	C17—C16—C19—C22	−59.1 (5)
C3—N4—C5—C6	−1.9 (5)	N15—C16—C19—C20	−61.5 (4)
C3—N4—C5—C51	176.3 (3)	C17—C16—C19—C20	179.5 (3)
N2—N1—C6—C5	−4.2 (5)	N15—C16—C19—C21	−179.2 (3)
N2—N1—C6—C61	175.7 (3)	C17—C16—C19—C21	61.8 (5)
N4—C5—C6—N1	6.0 (5)	N4—C5—C51—C56	−148.3 (4)
C51—C5—C6—N1	−172.0 (3)	C6—C5—C51—C56	29.8 (6)
N4—C5—C6—C61	−174.0 (3)	N4—C5—C51—C52	26.6 (4)
C51—C5—C6—C61	8.0 (6)	C6—C5—C51—C52	−155.3 (3)
C3—N7—C8—C13	−12.4 (6)	C56—C51—C52—C53	0.0 (5)
C3—N7—C8—C9	168.3 (4)	C5—C51—C52—C53	−175.1 (3)
C13—C8—C9—C10	2.8 (5)	C51—C52—C53—C54	0.1 (6)
N7—C8—C9—C10	−177.8 (3)	C52—C53—C54—C55	−0.4 (7)
C13—C8—C9—C14	−178.7 (3)	C53—C54—C55—C56	0.5 (7)
N7—C8—C9—C14	0.7 (5)	C54—C55—C56—C51	−0.4 (6)
C8—C9—C10—C11	−1.1 (6)	C52—C51—C56—C55	0.1 (5)
C14—C9—C10—C11	−179.6 (4)	C5—C51—C56—C55	174.9 (3)
C9—C10—C11—C12	−0.7 (6)	N1—C6—C61—C66	54.0 (5)
C10—C11—C12—C13	0.8 (7)	C5—C6—C61—C66	−126.1 (4)
C11—C12—C13—C8	0.9 (6)	N1—C6—C61—C62	−125.2 (4)
N7—C8—C13—C12	177.9 (4)	C5—C6—C61—C62	54.7 (5)
C9—C8—C13—C12	−2.8 (6)	C66—C61—C62—C63	1.4 (6)
C16—N15—C14—O18	0.8 (5)	C6—C61—C62—C63	−179.4 (4)
C16—N15—C14—C9	−178.1 (3)	C61—C62—C63—C64	0.2 (8)
C17—O18—C14—N15	1.9 (4)	C62—C63—C64—C65	−0.7 (9)
C17—O18—C14—C9	−179.1 (3)	C63—C64—C65—C66	−0.4 (8)
C10—C9—C14—N15	179.6 (4)	C62—C61—C66—C65	−2.5 (6)
C8—C9—C14—N15	1.2 (6)	C6—C61—C66—C65	178.3 (4)
C10—C9—C14—O18	0.7 (5)	C64—C65—C66—C61	2.0 (7)
C8—C9—C14—O18	−177.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···N15	0.97 (4)	1.87 (5)	2.671 (4)	138 (4)
C13—H13···N2	0.93	2.31	2.919 (5)	122
C53—H53···O18i	0.93	2.54	3.250 (5)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7⋯N15	0.97 (4)	1.87 (5)	2.671 (4)	138 (4)
C13—H13⋯N2	0.93	2.31	2.919 (5)	122
C53—H53⋯O18i	0.93	2.54	3.250 (5)	133

Symmetry code: (i) .