2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yl N-ethyl-carbamate.

The title compound, C(13)H(17)NO(3), crystallizes with two independent mol-ecules in the asymmetric unit. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules, forming chains propagaiting in [100]. A weak C-H⋯O inter-action also occurs.

Related literature

For background on insecticides related to the title compound, see: Tomlin (1994 ▶). For a related structure, see Xu et al. (2005 ▶).

Experimental

Crystal data

C13H17NO3

M = 235.28

Orthorhombic,

a = 10.362 (2) Å

b = 13.962 (3) Å

c = 18.069 (4) Å

V = 2614.1 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.26 × 0.20 × 0.08 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.978, T max = 0.993

20967 measured reflections

3256 independent reflections

2338 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.154

S = 1.08

3256 reflections

322 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809044687/hb5190sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044687/hb5190Isup2.hkl

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

C13H17NO3	F(000) = 1008
Mr = 235.28	Dx = 1.196 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5268 reflections
a = 10.362 (2) Å	θ = 1.8–27.1°
b = 13.962 (3) Å	µ = 0.09 mm−1
c = 18.069 (4) Å	T = 293 K
V = 2614.1 (10) Å3	Prism, colourless
Z = 8	0.26 × 0.20 × 0.08 mm

Rigaku Saturn CCD area-detector diffractometer	3256 independent reflections
Radiation source: rotating anode	2338 reflections with I > 2σ(I)
confocal	Rint = 0.049
Detector resolution: 7.31 pixels mm-1	θmax = 27.2°, θmin = 1.8°
ω and φ scans	h = −10→13
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −17→17
Tmin = 0.978, Tmax = 0.993	l = −21→23
20967 measured 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)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.154	w = 1/[σ2(Fo2) + (0.083P)2] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
3256 reflections	Δρmax = 0.14 e Å−3
322 parameters	Δρmin = −0.14 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: 0.029 (3)

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
O1	0.9284 (3)	0.3257 (2)	0.01889 (15)	0.0801 (8)
O2	0.9054 (2)	0.50324 (18)	0.14502 (19)	0.0855 (9)
O3	0.7620 (2)	0.38179 (17)	0.13896 (15)	0.0725 (7)
O4	0.3318 (3)	0.79075 (16)	0.11613 (14)	0.0758 (7)
O5	0.2451 (2)	0.60024 (16)	0.08020 (14)	0.0688 (7)
O6	0.4027 (2)	0.51258 (19)	0.13447 (16)	0.0812 (8)
N1	0.6932 (3)	0.5302 (2)	0.12561 (19)	0.0709 (8)
N2	0.1916 (3)	0.4821 (2)	0.15411 (17)	0.0660 (8)
C1	1.0315 (4)	0.2815 (3)	−0.0269 (2)	0.0762 (10)
C2	1.1341 (5)	0.3563 (3)	−0.0360 (3)	0.1080 (16)
H2A	1.0989	0.4107	−0.0614	0.162*
H2B	1.2044	0.3303	−0.0641	0.162*
H2C	1.1647	0.3757	0.0119	0.162*
C3	0.9693 (6)	0.2508 (4)	−0.0979 (3)	0.127 (2)
H3A	0.9036	0.2043	−0.0875	0.190*
H3B	1.0332	0.2232	−0.1298	0.190*
H3C	0.9312	0.3054	−0.1217	0.190*
C4	1.0807 (5)	0.1960 (3)	0.0181 (2)	0.0931 (13)
H4A	1.0517	0.1360	−0.0033	0.112*
H4B	1.1743	0.1958	0.0205	0.112*
C5	1.0226 (4)	0.2114 (2)	0.0936 (2)	0.0729 (10)
C6	1.0378 (5)	0.1657 (3)	0.1605 (3)	0.0881 (12)
H6	1.0972	0.1161	0.1652	0.106*
C7	0.9655 (5)	0.1933 (3)	0.2198 (3)	0.0947 (13)
H7	0.9766	0.1626	0.2650	0.114*
C8	0.8759 (4)	0.2665 (3)	0.2138 (2)	0.0840 (12)
H8	0.8262	0.2840	0.2545	0.101*
C9	0.8606 (3)	0.3134 (2)	0.1472 (2)	0.0679 (9)
C10	0.9355 (3)	0.2866 (3)	0.0874 (2)	0.0662 (9)
C11	0.7964 (3)	0.4767 (2)	0.13721 (19)	0.0612 (8)
C12	0.6965 (4)	0.6335 (3)	0.1279 (3)	0.0935 (13)
H12A	0.6404	0.6590	0.0897	0.112*
H12B	0.7836	0.6554	0.1179	0.112*
C13	0.6545 (7)	0.6699 (4)	0.2009 (4)	0.136 (2)
H13A	0.5680	0.6489	0.2107	0.205*
H13B	0.6571	0.7387	0.2008	0.205*
H13C	0.7111	0.6459	0.2386	0.205*
C14	0.3854 (4)	0.8896 (3)	0.1104 (2)	0.0773 (10)
C15	0.4434 (6)	0.9120 (5)	0.1854 (3)	0.1229 (18)
H15A	0.3771	0.9094	0.2225	0.184*
H15B	0.4806	0.9749	0.1845	0.184*
H15C	0.5091	0.8658	0.1967	0.184*
C16	0.2739 (5)	0.9540 (3)	0.0911 (4)	0.127 (2)
H16A	0.2339	0.9318	0.0463	0.190*
H16B	0.3047	1.0182	0.0840	0.190*
H16C	0.2119	0.9532	0.1306	0.190*
C17	0.4848 (4)	0.8855 (3)	0.0467 (2)	0.0856 (11)
H17A	0.4712	0.9373	0.0119	0.103*
H17B	0.5723	0.8891	0.0656	0.103*
C18	0.4599 (3)	0.7908 (2)	0.0114 (2)	0.0647 (9)
C19	0.5074 (3)	0.7502 (3)	−0.0522 (2)	0.0731 (10)
H19	0.5640	0.7840	−0.0824	0.088*
C20	0.4699 (4)	0.6584 (3)	−0.0705 (2)	0.0833 (11)
H20	0.5022	0.6299	−0.1132	0.100*
C21	0.3851 (3)	0.6086 (3)	−0.0262 (2)	0.0729 (10)
H21	0.3603	0.5469	−0.0395	0.088*
C22	0.3368 (3)	0.6491 (2)	0.03737 (19)	0.0605 (8)
C23	0.3733 (3)	0.7411 (2)	0.05565 (19)	0.0584 (8)
C24	0.2899 (3)	0.5289 (2)	0.12496 (18)	0.0564 (8)
C25	0.2109 (4)	0.4110 (3)	0.2117 (2)	0.0874 (12)
H25A	0.2936	0.3798	0.2046	0.105*
H25B	0.1439	0.3627	0.2084	0.105*
C26	0.2072 (7)	0.4562 (6)	0.2855 (3)	0.166 (3)
H26A	0.2746	0.5031	0.2890	0.249*
H26B	0.2196	0.4081	0.3228	0.249*
H26C	0.1250	0.4866	0.2926	0.249*
H1	0.622 (4)	0.504 (2)	0.1267 (18)	0.056 (10)*
H2	0.117 (4)	0.503 (3)	0.144 (2)	0.072 (11)*

	U11	U22	U33	U12	U13	U23
O1	0.0670 (16)	0.0924 (17)	0.0808 (17)	0.0327 (14)	0.0019 (13)	−0.0074 (14)
O2	0.0409 (12)	0.0715 (15)	0.144 (2)	−0.0031 (11)	−0.0087 (15)	0.0076 (15)
O3	0.0450 (12)	0.0685 (14)	0.1038 (18)	0.0029 (11)	0.0026 (12)	−0.0232 (13)
O4	0.0812 (16)	0.0653 (13)	0.0811 (16)	−0.0084 (13)	0.0173 (13)	0.0042 (12)
O5	0.0460 (11)	0.0603 (12)	0.1001 (18)	0.0058 (10)	0.0084 (12)	0.0259 (12)
O6	0.0417 (12)	0.0868 (16)	0.115 (2)	0.0025 (11)	−0.0052 (13)	0.0285 (16)
N1	0.0387 (15)	0.0758 (19)	0.098 (2)	0.0029 (14)	−0.0018 (15)	0.0000 (17)
N2	0.0449 (15)	0.0672 (16)	0.086 (2)	−0.0045 (14)	−0.0054 (14)	0.0208 (15)
C1	0.064 (2)	0.084 (2)	0.081 (2)	0.023 (2)	0.0069 (18)	−0.012 (2)
C2	0.091 (3)	0.090 (3)	0.143 (4)	0.013 (3)	0.032 (3)	−0.007 (3)
C3	0.122 (4)	0.151 (5)	0.107 (4)	0.045 (4)	−0.030 (3)	−0.049 (3)
C4	0.084 (3)	0.092 (3)	0.104 (3)	0.034 (2)	0.010 (2)	−0.003 (2)
C5	0.064 (2)	0.0597 (18)	0.094 (3)	0.0074 (17)	0.0040 (19)	−0.0047 (19)
C6	0.095 (3)	0.062 (2)	0.107 (3)	0.016 (2)	0.003 (3)	0.004 (2)
C7	0.110 (4)	0.072 (2)	0.102 (3)	0.010 (3)	0.013 (3)	0.008 (2)
C8	0.095 (3)	0.070 (2)	0.086 (3)	−0.006 (2)	0.019 (2)	−0.006 (2)
C9	0.0520 (18)	0.0592 (18)	0.093 (3)	−0.0028 (15)	0.0054 (18)	−0.0162 (18)
C10	0.0541 (19)	0.0673 (19)	0.077 (2)	0.0050 (16)	−0.0014 (17)	−0.0106 (18)
C11	0.0451 (17)	0.0670 (19)	0.072 (2)	−0.0005 (15)	0.0029 (15)	−0.0018 (17)
C12	0.063 (2)	0.082 (2)	0.135 (4)	0.007 (2)	0.000 (3)	0.029 (3)
C13	0.147 (5)	0.094 (3)	0.168 (5)	0.004 (4)	−0.023 (5)	−0.044 (3)
C14	0.073 (2)	0.0630 (19)	0.096 (3)	−0.0086 (18)	0.004 (2)	−0.0076 (19)
C15	0.124 (4)	0.136 (4)	0.108 (4)	−0.031 (4)	0.006 (3)	−0.024 (3)
C16	0.091 (3)	0.076 (3)	0.213 (6)	0.008 (3)	0.011 (4)	0.015 (3)
C17	0.084 (3)	0.077 (2)	0.096 (3)	−0.021 (2)	0.006 (2)	0.011 (2)
C18	0.0516 (18)	0.0676 (19)	0.075 (2)	−0.0058 (16)	−0.0013 (16)	0.0140 (18)
C19	0.0522 (19)	0.092 (3)	0.075 (2)	−0.0105 (19)	0.0040 (18)	0.012 (2)
C20	0.063 (2)	0.102 (3)	0.085 (3)	−0.004 (2)	0.015 (2)	−0.012 (2)
C21	0.058 (2)	0.069 (2)	0.092 (3)	−0.0068 (17)	0.0035 (19)	−0.002 (2)
C22	0.0447 (16)	0.0575 (17)	0.079 (2)	0.0017 (14)	0.0040 (16)	0.0155 (16)
C23	0.0476 (17)	0.0603 (17)	0.0673 (19)	−0.0004 (14)	0.0007 (15)	0.0105 (15)
C24	0.0436 (16)	0.0517 (15)	0.074 (2)	−0.0015 (13)	−0.0072 (15)	0.0029 (16)
C25	0.070 (2)	0.087 (3)	0.106 (3)	−0.003 (2)	0.000 (2)	0.037 (2)
C26	0.187 (7)	0.215 (7)	0.096 (4)	0.112 (6)	0.043 (4)	0.060 (4)

O1—C10	1.356 (5)	C8—H8	0.9300
O1—C1	1.486 (4)	C9—C10	1.381 (5)
O2—C11	1.198 (4)	C12—C13	1.478 (7)
O3—C11	1.373 (4)	C12—H12A	0.9700
O3—C9	1.406 (4)	C12—H12B	0.9700
O4—C23	1.364 (4)	C13—H13A	0.9600
O4—C14	1.491 (4)	C13—H13B	0.9600
O5—C24	1.365 (4)	C13—H13C	0.9600
O5—C22	1.402 (4)	C14—C16	1.506 (6)
O6—C24	1.203 (4)	C14—C15	1.515 (6)
N1—C11	1.321 (4)	C14—C17	1.545 (6)
N1—C12	1.443 (5)	C15—H15A	0.9600
N1—H1	0.82 (4)	C15—H15B	0.9600
N2—C24	1.320 (4)	C15—H15C	0.9600
N2—C25	1.451 (5)	C16—H16A	0.9600
N2—H2	0.84 (4)	C16—H16B	0.9600
C1—C3	1.497 (6)	C16—H16C	0.9600
C1—C2	1.498 (6)	C17—C18	1.491 (5)
C1—C4	1.532 (6)	C17—H17A	0.9700
C2—H2A	0.9600	C17—H17B	0.9700
C2—H2B	0.9600	C18—C19	1.372 (5)
C2—H2C	0.9600	C18—C23	1.389 (4)
C3—H3A	0.9600	C19—C20	1.379 (6)
C3—H3B	0.9600	C19—H19	0.9300
C3—H3C	0.9600	C20—C21	1.377 (5)
C4—C5	1.506 (6)	C20—H20	0.9300
C4—H4A	0.9700	C21—C22	1.375 (5)
C4—H4B	0.9700	C21—H21	0.9300
C5—C6	1.376 (6)	C22—C23	1.379 (5)
C5—C10	1.389 (5)	C25—C26	1.475 (7)
C6—C7	1.364 (6)	C25—H25A	0.9700
C6—H6	0.9300	C25—H25B	0.9700
C7—C8	1.385 (6)	C26—H26A	0.9600
C7—H7	0.9300	C26—H26B	0.9600
C8—C9	1.379 (6)	C26—H26C	0.9600
C10—O1—C1	107.6 (3)	C12—C13—H13B	109.5
C11—O3—C9	118.0 (2)	H13A—C13—H13B	109.5
C23—O4—C14	107.3 (3)	C12—C13—H13C	109.5
C24—O5—C22	116.8 (2)	H13A—C13—H13C	109.5
C11—N1—C12	122.8 (3)	H13B—C13—H13C	109.5
C11—N1—H1	118 (2)	O4—C14—C16	106.5 (3)
C12—N1—H1	117 (2)	O4—C14—C15	106.0 (4)
C24—N2—C25	121.2 (3)	C16—C14—C15	112.8 (4)
C24—N2—H2	117 (3)	O4—C14—C17	105.4 (3)
C25—N2—H2	121 (3)	C16—C14—C17	111.2 (4)
O1—C1—C3	106.6 (3)	C15—C14—C17	114.2 (4)
O1—C1—C2	106.3 (3)	C14—C15—H15A	109.5
C3—C1—C2	114.3 (4)	C14—C15—H15B	109.5
O1—C1—C4	105.5 (3)	H15A—C15—H15B	109.5
C3—C1—C4	112.0 (4)	C14—C15—H15C	109.5
C2—C1—C4	111.4 (4)	H15A—C15—H15C	109.5
C1—C2—H2A	109.5	H15B—C15—H15C	109.5
C1—C2—H2B	109.5	C14—C16—H16A	109.5
H2A—C2—H2B	109.5	C14—C16—H16B	109.5
C1—C2—H2C	109.5	H16A—C16—H16B	109.5
H2A—C2—H2C	109.5	C14—C16—H16C	109.5
H2B—C2—H2C	109.5	H16A—C16—H16C	109.5
C1—C3—H3A	109.5	H16B—C16—H16C	109.5
C1—C3—H3B	109.5	C18—C17—C14	103.7 (3)
H3A—C3—H3B	109.5	C18—C17—H17A	111.0
C1—C3—H3C	109.5	C14—C17—H17A	111.0
H3A—C3—H3C	109.5	C18—C17—H17B	111.0
H3B—C3—H3C	109.5	C14—C17—H17B	111.0
C5—C4—C1	103.7 (3)	H17A—C17—H17B	109.0
C5—C4—H4A	111.0	C19—C18—C23	120.5 (3)
C1—C4—H4A	111.0	C19—C18—C17	131.5 (3)
C5—C4—H4B	111.0	C23—C18—C17	108.0 (3)
C1—C4—H4B	111.0	C18—C19—C20	118.9 (3)
H4A—C4—H4B	109.0	C18—C19—H19	120.6
C6—C5—C10	119.7 (4)	C20—C19—H19	120.6
C6—C5—C4	133.1 (3)	C21—C20—C19	120.7 (4)
C10—C5—C4	107.2 (3)	C21—C20—H20	119.7
C7—C6—C5	119.8 (4)	C19—C20—H20	119.7
C7—C6—H6	120.1	C22—C21—C20	120.7 (4)
C5—C6—H6	120.1	C22—C21—H21	119.7
C6—C7—C8	121.0 (4)	C20—C21—H21	119.7
C6—C7—H7	119.5	C21—C22—C23	118.9 (3)
C8—C7—H7	119.5	C21—C22—O5	120.6 (3)
C9—C8—C7	119.7 (4)	C23—C22—O5	120.4 (3)
C9—C8—H8	120.2	O4—C23—C22	125.4 (3)
C7—C8—H8	120.2	O4—C23—C18	114.3 (3)
C8—C9—C10	119.3 (3)	C22—C23—C18	120.3 (3)
C8—C9—O3	119.8 (3)	O6—C24—N2	126.8 (3)
C10—C9—O3	120.6 (3)	O6—C24—O5	123.6 (3)
O1—C10—C9	125.1 (3)	N2—C24—O5	109.6 (3)
O1—C10—C5	114.4 (3)	N2—C25—C26	110.6 (4)
C9—C10—C5	120.5 (3)	N2—C25—H25A	109.5
O2—C11—N1	127.4 (3)	C26—C25—H25A	109.5
O2—C11—O3	122.7 (3)	N2—C25—H25B	109.5
N1—C11—O3	109.9 (3)	C26—C25—H25B	109.5
N1—C12—C13	111.3 (4)	H25A—C25—H25B	108.1
N1—C12—H12A	109.4	C25—C26—H26A	109.5
C13—C12—H12A	109.4	C25—C26—H26B	109.5
N1—C12—H12B	109.4	H26A—C26—H26B	109.5
C13—C12—H12B	109.4	C25—C26—H26C	109.5
H12A—C12—H12B	108.0	H26A—C26—H26C	109.5
C12—C13—H13A	109.5	H26B—C26—H26C	109.5
C10—O1—C1—C3	131.3 (4)	C23—O4—C14—C16	107.5 (4)
C10—O1—C1—C2	−106.3 (4)	C23—O4—C14—C15	−132.1 (4)
C10—O1—C1—C4	12.1 (4)	C23—O4—C14—C17	−10.7 (4)
O1—C1—C4—C5	−12.4 (4)	O4—C14—C17—C18	11.4 (4)
C3—C1—C4—C5	−128.0 (4)	C16—C14—C17—C18	−103.6 (4)
C2—C1—C4—C5	102.6 (4)	C15—C14—C17—C18	127.4 (4)
C1—C4—C5—C6	−173.3 (4)	C14—C17—C18—C19	172.3 (4)
C1—C4—C5—C10	8.7 (5)	C14—C17—C18—C23	−8.4 (4)
C10—C5—C6—C7	1.2 (6)	C23—C18—C19—C20	−1.4 (5)
C4—C5—C6—C7	−176.6 (5)	C17—C18—C19—C20	177.9 (4)
C5—C6—C7—C8	0.5 (7)	C18—C19—C20—C21	0.7 (6)
C6—C7—C8—C9	−1.1 (7)	C19—C20—C21—C22	−0.4 (6)
C7—C8—C9—C10	−0.1 (6)	C20—C21—C22—C23	0.8 (5)
C7—C8—C9—O3	174.4 (3)	C20—C21—C22—O5	176.5 (3)
C11—O3—C9—C8	106.3 (4)	C24—O5—C22—C21	78.1 (4)
C11—O3—C9—C10	−79.3 (4)	C24—O5—C22—C23	−106.3 (3)
C1—O1—C10—C9	175.9 (3)	C14—O4—C23—C22	−174.8 (3)
C1—O1—C10—C5	−6.9 (4)	C14—O4—C23—C18	5.7 (4)
C8—C9—C10—O1	178.9 (4)	C21—C22—C23—O4	179.0 (3)
O3—C9—C10—O1	4.4 (5)	O5—C22—C23—O4	3.3 (5)
C8—C9—C10—C5	1.8 (5)	C21—C22—C23—C18	−1.6 (5)
O3—C9—C10—C5	−172.6 (3)	O5—C22—C23—C18	−177.2 (3)
C6—C5—C10—O1	−179.7 (4)	C19—C18—C23—O4	−178.6 (3)
C4—C5—C10—O1	−1.4 (5)	C17—C18—C23—O4	2.0 (4)
C6—C5—C10—C9	−2.4 (6)	C19—C18—C23—C22	1.9 (5)
C4—C5—C10—C9	175.9 (3)	C17—C18—C23—C22	−177.5 (3)
C12—N1—C11—O2	−6.4 (7)	C25—N2—C24—O6	9.2 (6)
C12—N1—C11—O3	173.9 (3)	C25—N2—C24—O5	−171.5 (3)
C9—O3—C11—O2	−2.7 (5)	C22—O5—C24—O6	7.3 (5)
C9—O3—C11—N1	176.9 (3)	C22—O5—C24—N2	−172.0 (3)
C11—N1—C12—C13	−96.9 (5)	C24—N2—C25—C26	89.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6	0.82 (4)	2.28 (4)	3.024 (4)	151 (3)
N2—H2···O2i	0.84 (4)	2.19 (4)	2.985 (4)	156 (3)
C19—H19···O5ii	0.93	2.48	3.269 (4)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O6	0.82 (4)	2.28 (4)	3.024 (4)	151 (3)
N2—H2⋯O2i	0.84 (4)	2.19 (4)	2.985 (4)	156 (3)
C19—H19⋯O5ii	0.93	2.48	3.269 (4)	143

Symmetry codes: (i) ; (ii) .