3-Butyl-2-propyl-amino-1-benzo-thieno[3,2-d]pyrimidin-4(3H)-one.

In the title compound, C(17)H(21)N(3)OS, the propyl and butyl groups are disordered over two positions; site occupation factors are 0.304 (10) and 0.696 (10). The three fused rings are coplanar. In the crystal structure, inter-molecular N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules. Further stability is provided by offset π-π stacking inter-actions. Adjacent thienophene-pyrimidine and pyrimidine-benzene rings have centroid-centroid distances of 3.96 (1) and 3.55 (2) Å, respectively.

Related literature

For general background, see: Chambhare et al. (2003 ▶); Janiak (2000 ▶). For related literature, see: Ding et al. (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H21N3OS

M = 315.43

Monoclinic,

a = 11.4322 (6) Å

b = 14.2791 (8) Å

c = 11.6704 (6) Å

β = 116.606 (1)°

V = 1703.36 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 298 (2) K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer

Absorption correction: none

15640 measured reflections

3712 independent reflections

2599 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.175

S = 1.04

3712 reflections

279 parameters

23 restraints

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807062484/hk2396sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062484/hk2396Isup2.hkl

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

C17H21N3OS	F000 = 672
Mr = 315.43	Dx = 1.230 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4476 reflections
a = 11.4322 (6) Å	θ = 2.4–24.2º
b = 14.2791 (8) Å	µ = 0.20 mm−1
c = 11.6704 (6) Å	T = 298 (2) K
β = 116.606 (1)º	Block, colorless
V = 1703.36 (16) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker SMART 4K CCD area-detector diffractometer	2599 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.054
Monochromator: graphite	θmax = 27.0º
T = 298(2) K	θmin = 2.0º
φ and ω scans	h = −14→14
Absorption correction: none	k = −17→18
15640 measured reflections	l = −14→14
3712 independent reflections

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)] = 0.058	H-atom parameters constrained
wR(F2) = 0.175	w = 1/[σ2(Fo2) + (0.107P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.004
3712 reflections	Δρmax = 0.35 e Å−3
279 parameters	Δρmin = −0.15 e Å−3
23 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

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	Occ. (<1)
S1	0.13711 (6)	0.04643 (4)	1.26890 (6)	0.0767 (3)
O1	0.22957 (17)	0.23409 (10)	1.18589 (13)	0.0782 (5)
N1	0.21439 (19)	−0.00118 (12)	0.97855 (15)	0.0679 (5)
N2	0.25553 (18)	0.16172 (11)	1.02369 (15)	0.0646 (5)
N3	0.2992 (7)	0.0903 (4)	0.8663 (6)	0.0835 (17)	0.696 (10)
H3A	0.3215	0.1450	0.8524	0.100*	0.696 (10)
N3'	0.2371 (11)	0.0885 (9)	0.8333 (9)	0.057 (2)	0.304 (10)
H3'	0.2257	0.1427	0.7977	0.068*	0.304 (10)
C1	0.14037 (18)	−0.08829 (14)	1.11773 (18)	0.0588 (5)
C2	0.1241 (2)	−0.17839 (15)	1.0674 (2)	0.0775 (6)
H2	0.1433	−0.1913	0.9995	0.093*
C3	0.0795 (3)	−0.24799 (17)	1.1191 (3)	0.0921 (8)
H3	0.0683	−0.3082	1.0855	0.110*
C4	0.0510 (3)	−0.2299 (2)	1.2203 (3)	0.0969 (8)
H4	0.0207	−0.2780	1.2539	0.116*
C5	0.0668 (3)	−0.14217 (19)	1.2713 (3)	0.0897 (7)
H5	0.0479	−0.1303	1.3396	0.108*
C6	0.1117 (2)	−0.07033 (16)	1.2202 (2)	0.0663 (5)
C7	0.18358 (19)	−0.00435 (13)	1.07820 (16)	0.0550 (5)
C8	0.1850 (2)	0.07176 (14)	1.15013 (17)	0.0569 (5)
C9	0.2227 (2)	0.16126 (14)	1.12618 (17)	0.0585 (5)
C10	0.2479 (2)	0.08120 (15)	0.95393 (19)	0.0708 (6)
C11	0.3166 (9)	0.0091 (5)	0.7964 (8)	0.115 (3)	0.696 (10)
H11	0.3261	−0.0490	0.8446	0.138*	0.696 (10)
C11'	0.2443 (15)	0.0099 (9)	0.7669 (9)	0.085 (5)	0.304 (10)
H11'	0.1795	−0.0319	0.7733	0.102*	0.304 (10)
C12	0.4388 (5)	0.0288 (5)	0.7817 (5)	0.118 (2)	0.696 (10)
H12A	0.4292	0.0873	0.7377	0.177*	0.696 (10)
H12B	0.4525	−0.0206	0.7332	0.177*	0.696 (10)
H12C	0.5125	0.0324	0.8648	0.177*	0.696 (10)
C12'	0.3646 (15)	−0.0512 (13)	0.8141 (10)	0.149 (9)	0.304 (10)
H12D	0.4229	−0.0277	0.7820	0.223*	0.304 (10)
H12E	0.3395	−0.1142	0.7843	0.223*	0.304 (10)
H12F	0.4080	−0.0507	0.9061	0.223*	0.304 (10)
C13	0.1988 (6)	0.0047 (7)	0.6697 (10)	0.139 (4)	0.696 (10)
H13A	0.1233	−0.0101	0.6821	0.208*	0.696 (10)
H13B	0.2109	−0.0429	0.6179	0.208*	0.696 (10)
H13C	0.1862	0.0641	0.6274	0.208*	0.696 (10)
C13'	0.1899 (19)	0.0248 (14)	0.6251 (10)	0.128 (8)	0.304 (10)
H13D	0.1081	0.0574	0.5945	0.193*	0.304 (10)
H13E	0.1764	−0.0348	0.5829	0.193*	0.304 (10)
H13F	0.2504	0.0611	0.6072	0.193*	0.304 (10)
C14	0.3278 (9)	0.2503 (6)	1.0136 (9)	0.079 (3)	0.622 (11)
H14A	0.3095	0.2584	0.9247	0.095*	0.622 (11)
H14B	0.2914	0.3040	1.0374	0.095*	0.622 (11)
C14'	0.2809 (11)	0.2515 (8)	0.9807 (12)	0.055 (2)	0.378 (11)
H14C	0.2538	0.3028	1.0179	0.066*	0.378 (11)
H14D	0.2356	0.2564	0.8881	0.066*	0.378 (11)
C15	0.4741 (8)	0.2515 (6)	1.0939 (8)	0.128 (3)	0.622 (11)
H15A	0.5120	0.1976	1.0725	0.154*	0.622 (11)
H15B	0.4941	0.2468	1.1838	0.154*	0.622 (11)
C15'	0.4291 (10)	0.2516 (6)	1.0287 (12)	0.082 (3)	0.378 (11)
H15C	0.4555	0.1983	0.9941	0.099*	0.378 (11)
H15D	0.4733	0.2479	1.1215	0.099*	0.378 (11)
C16	0.5353 (10)	0.3408 (6)	1.0727 (9)	0.174 (4)	0.622 (11)
H16A	0.4767	0.3931	1.0603	0.209*	0.622 (11)
H16B	0.6166	0.3535	1.1483	0.209*	0.622 (11)
C16'	0.4644 (9)	0.3432 (6)	0.9833 (10)	0.100 (3)	0.378 (11)
H16C	0.4288	0.3431	0.8907	0.120*	0.378 (11)
H16D	0.4274	0.3959	1.0083	0.120*	0.378 (11)
C17	0.5612 (12)	0.3325 (9)	0.9614 (9)	0.179 (4)	0.622 (11)
H17A	0.6154	0.2788	0.9714	0.269*	0.622 (11)
H17B	0.6053	0.3878	0.9543	0.269*	0.622 (11)
H17C	0.4800	0.3255	0.8854	0.269*	0.622 (11)
C17'	0.6098 (10)	0.3518 (14)	1.0427 (18)	0.194 (9)	0.378 (11)
H17D	0.6484	0.3093	1.1136	0.291*	0.378 (11)
H17E	0.6347	0.4148	1.0725	0.291*	0.378 (11)
H17F	0.6399	0.3370	0.9801	0.291*	0.378 (11)

	U11	U22	U33	U12	U13	U23
S1	0.1169 (5)	0.0600 (4)	0.0808 (4)	−0.0027 (3)	0.0688 (4)	−0.0042 (3)
O1	0.1334 (13)	0.0518 (9)	0.0645 (8)	−0.0032 (8)	0.0578 (9)	−0.0075 (7)
N1	0.1108 (14)	0.0461 (10)	0.0552 (9)	0.0177 (9)	0.0447 (9)	0.0053 (7)
N2	0.1050 (12)	0.0456 (9)	0.0533 (9)	0.0107 (8)	0.0445 (9)	0.0074 (7)
N3	0.142 (5)	0.057 (2)	0.080 (3)	0.027 (3)	0.075 (4)	0.017 (2)
N3'	0.087 (6)	0.043 (3)	0.047 (4)	0.017 (4)	0.035 (4)	0.007 (3)
C1	0.0655 (11)	0.0501 (11)	0.0567 (10)	0.0086 (9)	0.0237 (9)	0.0051 (8)
C2	0.1061 (17)	0.0522 (13)	0.0719 (13)	0.0070 (11)	0.0378 (12)	0.0010 (10)
C3	0.1158 (19)	0.0537 (14)	0.0965 (18)	−0.0102 (13)	0.0384 (16)	−0.0010 (13)
C4	0.112 (2)	0.0737 (18)	0.109 (2)	−0.0186 (15)	0.0540 (17)	0.0101 (15)
C5	0.1149 (19)	0.0739 (17)	0.1055 (19)	−0.0128 (14)	0.0718 (16)	0.0048 (14)
C6	0.0756 (13)	0.0568 (12)	0.0731 (12)	0.0011 (9)	0.0393 (11)	0.0019 (10)
C7	0.0678 (11)	0.0480 (11)	0.0457 (9)	0.0132 (8)	0.0222 (8)	0.0056 (8)
C8	0.0749 (12)	0.0507 (11)	0.0504 (10)	0.0084 (9)	0.0329 (9)	0.0028 (8)
C9	0.0841 (13)	0.0485 (11)	0.0482 (10)	0.0082 (9)	0.0343 (9)	0.0024 (8)
C10	0.1190 (17)	0.0495 (12)	0.0595 (11)	0.0226 (11)	0.0538 (12)	0.0090 (9)
C11	0.212 (8)	0.070 (3)	0.125 (5)	0.050 (5)	0.132 (6)	0.024 (3)
C11'	0.175 (13)	0.053 (6)	0.055 (6)	0.052 (8)	0.078 (8)	0.018 (4)
C12	0.126 (4)	0.135 (5)	0.105 (3)	0.038 (3)	0.063 (3)	−0.008 (3)
C12'	0.204 (15)	0.134 (14)	0.103 (8)	0.106 (12)	0.065 (8)	0.010 (7)
C13	0.131 (6)	0.111 (6)	0.210 (11)	−0.033 (4)	0.109 (7)	−0.089 (7)
C13'	0.221 (19)	0.089 (10)	0.040 (5)	0.019 (10)	0.028 (6)	−0.016 (5)
C14	0.126 (7)	0.059 (3)	0.053 (4)	0.006 (4)	0.041 (5)	0.013 (2)
C14'	0.088 (6)	0.038 (3)	0.049 (6)	0.004 (4)	0.039 (5)	0.002 (3)
C15	0.113 (5)	0.155 (6)	0.090 (5)	−0.047 (4)	0.022 (4)	0.025 (4)
C15'	0.078 (6)	0.084 (5)	0.080 (6)	−0.012 (4)	0.032 (5)	0.014 (4)
C16	0.145 (7)	0.237 (10)	0.135 (8)	−0.084 (6)	0.058 (6)	−0.015 (6)
C16'	0.112 (6)	0.109 (6)	0.073 (5)	−0.034 (5)	0.034 (5)	−0.001 (4)
C17	0.162 (9)	0.259 (12)	0.140 (7)	−0.051 (8)	0.088 (7)	0.006 (8)
C17'	0.157 (12)	0.262 (19)	0.145 (14)	−0.116 (13)	0.052 (10)	0.013 (14)

N3—C11	1.482 (9)	C12'—H12D	0.9600
N3—H3A	0.8600	C12'—H12E	0.9600
N3'—C11'	1.387 (16)	C12'—H12F	0.9600
N3'—H3'	0.8600	C13—H13A	0.9600
C1—C2	1.392 (3)	C13—H13B	0.9600
C1—C6	1.397 (3)	C13—H13C	0.9600
C1—C7	1.448 (3)	C13'—H13D	0.9600
C2—C3	1.374 (3)	C13'—H13E	0.9600
C2—H2	0.9300	C13'—H13F	0.9600
C3—C4	1.384 (4)	C14—C15	1.507 (7)
C3—H3	0.9300	C14—N2	1.544 (7)
C4—C5	1.364 (4)	C14—H14A	0.9700
C4—H4	0.9300	C14—H14B	0.9700
C5—C6	1.395 (3)	C14'—N2	1.452 (9)
C5—H5	0.9300	C14'—C15'	1.528 (9)
C6—S1	1.743 (2)	C14'—H14C	0.9700
C7—N1	1.359 (3)	C14'—H14D	0.9700
C7—C8	1.369 (3)	C15—C16	1.528 (7)
C8—C9	1.416 (3)	C15—H15A	0.9700
C8—S1	1.741 (2)	C15—H15B	0.9700
C9—O1	1.235 (2)	C15'—C16'	1.531 (8)
C9—N2	1.405 (2)	C15'—H15C	0.9700
C10—N1	1.308 (3)	C15'—H15D	0.9700
C10—N3'	1.361 (10)	C16—C17	1.461 (8)
C10—N2	1.389 (3)	C16—H16A	0.9700
C10—N3	1.394 (5)	C16—H16B	0.9700
C11—C13	1.490 (7)	C16'—C17'	1.493 (9)
C11—C12	1.508 (7)	C16'—H16C	0.9700
C11—H11	0.9800	C16'—H16D	0.9700
C11'—C13'	1.499 (9)	C17—H17A	0.9600
C11'—C12'	1.510 (9)	C17—H17B	0.9600
C11'—H11'	0.9800	C17—H17C	0.9600
C12—H12A	0.9600	C17'—H17D	0.9600
C12—H12B	0.9600	C17'—H17E	0.9600
C12—H12C	0.9600	C17'—H17F	0.9600
C8—S1—C6	90.27 (10)	C12'—C11'—H11'	102.4
C10—N1—C7	115.57 (16)	C11'—C12'—H12D	109.5
C10—N2—C9	121.65 (17)	C11'—C12'—H12E	109.5
C10—N2—C14'	119.9 (6)	H12D—C12'—H12E	109.5
C9—N2—C14'	118.0 (6)	C11'—C12'—H12F	109.5
C10—N2—C14	121.9 (4)	H12D—C12'—H12F	109.5
C9—N2—C14	115.1 (4)	H12E—C12'—H12F	109.5
C10—N3—C11	122.4 (6)	C11'—C13'—H13D	109.5
C10—N3—H3A	118.8	C11'—C13'—H13E	109.5
C11—N3—H3A	118.8	H13D—C13'—H13E	109.5
C10—N3'—C11'	121.0 (10)	C11'—C13'—H13F	109.5
C10—N3'—H3'	119.5	H13D—C13'—H13F	109.5
C11'—N3'—H3'	119.5	H13E—C13'—H13F	109.5
C2—C1—C6	119.5 (2)	C15—C14—N2	116.4 (6)
C2—C1—C7	129.1 (2)	C15—C14—H14A	108.2
C6—C1—C7	111.39 (18)	N2—C14—H14A	108.2
C3—C2—C1	119.2 (2)	C15—C14—H14B	108.2
C3—C2—H2	120.4	N2—C14—H14B	108.2
C1—C2—H2	120.4	H14A—C14—H14B	107.3
C2—C3—C4	121.1 (2)	N2—C14'—C15'	103.6 (7)
C2—C3—H3	119.5	N2—C14'—H14C	111.0
C4—C3—H3	119.5	C15'—C14'—H14C	111.0
C5—C4—C3	120.5 (2)	N2—C14'—H14D	111.0
C5—C4—H4	119.7	C15'—C14'—H14D	111.0
C3—C4—H4	119.7	H14C—C14'—H14D	109.0
C4—C5—C6	119.4 (3)	C14—C15—C16	111.7 (6)
C4—C5—H5	120.3	C14—C15—H15A	109.3
C6—C5—H5	120.3	C16—C15—H15A	109.3
C5—C6—C1	120.2 (2)	C14—C15—H15B	109.3
C5—C6—S1	127.07 (19)	C16—C15—H15B	109.3
C1—C6—S1	112.71 (16)	H15A—C15—H15B	107.9
N1—C7—C8	124.20 (18)	C14'—C15'—C16'	107.1 (7)
N1—C7—C1	123.82 (17)	C14'—C15'—H15C	110.3
C8—C7—C1	111.94 (18)	C16'—C15'—H15C	110.3
C7—C8—C9	121.09 (18)	C14'—C15'—H15D	110.3
C7—C8—S1	113.69 (15)	C16'—C15'—H15D	110.3
C9—C8—S1	125.23 (15)	H15C—C15'—H15D	108.5
O1—C9—N2	120.20 (18)	C17—C16—C15	111.5 (7)
O1—C9—C8	126.63 (18)	C17—C16—H16A	109.3
N2—C9—C8	113.17 (16)	C15—C16—H16A	109.3
N1—C10—N3'	113.4 (6)	C17—C16—H16B	109.3
N1—C10—N2	124.28 (18)	C15—C16—H16B	109.3
N3'—C10—N2	119.7 (5)	H16A—C16—H16B	108.0
N1—C10—N3	120.3 (3)	C17'—C16'—C15'	108.7 (7)
N2—C10—N3	114.6 (3)	C17'—C16'—H16C	109.9
N3—C11—C13	107.2 (6)	C15'—C16'—H16C	109.9
N3—C11—C12	106.0 (6)	C17'—C16'—H16D	109.9
C13—C11—C12	111.5 (5)	C15'—C16'—H16D	109.9
N3—C11—H11	110.7	H16C—C16'—H16D	108.3
C13—C11—H11	110.7	C16'—C17'—H17D	109.5
C12—C11—H11	110.7	C16'—C17'—H17E	109.5
N3'—C11'—C13'	113.8 (11)	H17D—C17'—H17E	109.5
N3'—C11'—C12'	122.5 (11)	C16'—C17'—H17F	109.5
C13'—C11'—C12'	110.1 (8)	H17D—C17'—H17F	109.5
N3'—C11'—H11'	102.4	H17E—C17'—H17F	109.5
C13'—C11'—H11'	102.4
C6—C1—C2—C3	0.3 (3)	C14—C15—C16—C17	−84.7 (12)
C7—C1—C2—C3	−178.9 (2)	N2—C14'—C15'—C16'	178.1 (8)
C1—C2—C3—C4	−0.2 (4)	C14'—C15'—C16'—C17'	172.6 (15)
C2—C3—C4—C5	−0.1 (4)	N3'—C10—N1—C7	−160.1 (5)
C3—C4—C5—C6	0.3 (4)	N2—C10—N1—C7	1.3 (3)
C4—C5—C6—C1	−0.1 (4)	N3—C10—N1—C7	170.8 (4)
C4—C5—C6—S1	179.2 (2)	C8—C7—N1—C10	0.5 (3)
C2—C1—C6—C5	−0.2 (3)	C1—C7—N1—C10	178.05 (18)
C7—C1—C6—C5	179.2 (2)	N1—C10—N2—C9	−2.2 (3)
C2—C1—C6—S1	−179.60 (17)	N3'—C10—N2—C9	158.1 (6)
C7—C1—C6—S1	−0.2 (2)	N3—C10—N2—C9	−172.3 (4)
C2—C1—C7—N1	1.2 (3)	N1—C10—N2—C14'	−173.8 (6)
C6—C1—C7—N1	−178.14 (17)	N3'—C10—N2—C14'	−13.5 (8)
C2—C1—C7—C8	178.9 (2)	N3—C10—N2—C14'	16.1 (7)
C6—C1—C7—C8	−0.4 (2)	N1—C10—N2—C14	164.2 (4)
N1—C7—C8—C9	−1.5 (3)	N3'—C10—N2—C14	−35.5 (7)
C1—C7—C8—C9	−179.22 (17)	N3—C10—N2—C14	−5.9 (6)
N1—C7—C8—S1	178.56 (15)	O1—C9—N2—C10	−179.5 (2)
C1—C7—C8—S1	0.8 (2)	C8—C9—N2—C10	1.1 (3)
C7—C8—C9—O1	−178.78 (19)	O1—C9—N2—C14'	−7.7 (6)
S1—C8—C9—O1	1.2 (3)	C8—C9—N2—C14'	172.9 (5)
C7—C8—C9—N2	0.5 (3)	O1—C9—N2—C14	13.3 (4)
S1—C8—C9—N2	−179.48 (14)	C8—C9—N2—C14	−166.1 (4)
N1—C10—N3—C11	0.8 (8)	C15'—C14'—N2—C10	−80.9 (8)
N3'—C10—N3—C11	−81.1 (18)	C15'—C14'—N2—C9	107.1 (8)
N2—C10—N3—C11	171.4 (5)	C15'—C14'—N2—C14	21 (2)
C10—N3—C11—C13	95.4 (8)	C15—C14—N2—C10	−82.4 (8)
C10—N3—C11—C12	−145.4 (7)	C15—C14—N2—C9	84.8 (8)
N1—C10—N3'—C11'	−25.1 (12)	C15—C14—N2—C14'	−172 (3)
N2—C10—N3'—C11'	172.6 (9)	C7—C8—S1—C6	−0.77 (16)
N3—C10—N3'—C11'	86.3 (17)	C9—C8—S1—C6	179.24 (19)
C10—N3'—C11'—C13'	161.8 (14)	C5—C6—S1—C8	−178.8 (2)
C10—N3'—C11'—C12'	−61.6 (18)	C1—C6—S1—C8	0.55 (16)
N2—C14—C15—C16	178.0 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O1i	0.97	2.52	3.478 (9)	171
N3—H3A···O1i	0.86	2.46	3.140 (6)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯O1i	0.97	2.52	3.478 (9)	171
N3—H3A⋯O1i	0.86	2.46	3.140 (6)	137

Symmetry code: (i) .