2-Amino-6-{[(6-chloropyridin-3-yl)methyl](ethyl)amino}-1-methyl-5-nitro-4-phenyl-1,4-dihydro-pyridine-3-carbonitrile ethanol monosolvate.

In the title compound, C(21)H(21)ClN(6)O(2)·C(2)H(6)O, a member of the insecticidal active neonicotinoid group of compounds, the 1,4-dihydro-pyridine ring adopts a boat conformation. An intra-molecular C-H⋯O hydrogen bond occurs while the components are linked by an N-H⋯O interaction. The crystal packing is stablized by O-H⋯N hydrogen bonds and C-H⋯O interactions.

Related literature

For the synthesis, see: Zhang et al. (2010 ▶). For the insectidal activity of nitenpyram [systematic name: (E)-N-(6-Chloro-3-pyridyl­meth­yl)-N-ethyl-N′-methyl-2-nitro­vinyl­idenediamine], see: Elbert & Nauen (2000 ▶); Jeschke & Nauen (2008 ▶); Kashiwada (1996 ▶); Minamida et al. (1993 ▶); Shao et al. (2008 ▶); Tomizawa & Casida (2009 ▶).

Experimental

Crystal data

C21H21ClN6O2·C2H6O

M = 470.96

Orthorhombic,

a = 19.3334 (19) Å

b = 12.1156 (12) Å

c = 20.644 (2) Å

V = 4835.5 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.19 mm−1

T = 298 K

0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS: Bruker, 2001 ▶) T min = 0.970, T max = 0.981

44471 measured reflections

4267 independent reflections

3044 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.135

S = 1.05

4267 reflections

330 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812011750/gg2077sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011750/gg2077Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812011750/gg2077Isup3.cml

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

C21H21ClN6O2·C2H6O	F(000) = 1984
Mr = 470.96	Dx = 1.294 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5913 reflections
a = 19.3334 (19) Å	θ = 2.2–20.1°
b = 12.1156 (12) Å	µ = 0.19 mm−1
c = 20.644 (2) Å	T = 298 K
V = 4835.5 (8) Å3	Block, yellow
Z = 8	0.16 × 0.12 × 0.10 mm

Bruker SMART CCD area-detector diffractometer	4267 independent reflections
Radiation source: fine-focus sealed tube	3044 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
phi and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS: Bruker, 2001)	h = −23→23
Tmin = 0.970, Tmax = 0.981	k = −14→14
44471 measured reflections	l = −24→24

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0687P)2 + 0.8771P] where P = (Fo2 + 2Fc2)/3
4267 reflections	(Δ/σ)max < 0.001
330 parameters	Δρmax = 0.21 e Å−3
4 restraints	Δρmin = −0.20 e Å−3

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	Occ. (<1)
C1	0.16697 (13)	0.1575 (2)	0.97037 (12)	0.0672 (6)
C2	0.16346 (13)	0.0715 (2)	0.92705 (12)	0.0677 (6)
H2	0.1423	0.0051	0.9379	0.081*
C3	0.19239 (11)	0.08776 (18)	0.86736 (11)	0.0594 (6)
H3	0.1913	0.0314	0.8368	0.071*
C4	0.22332 (10)	0.18758 (16)	0.85211 (10)	0.0509 (5)
C5	0.22151 (11)	0.26760 (19)	0.89890 (12)	0.0636 (6)
H5	0.2408	0.3359	0.8890	0.076*
C6	0.26080 (10)	0.20673 (18)	0.78962 (10)	0.0538 (5)
H6A	0.2766	0.2827	0.7884	0.065*
H6B	0.3014	0.1596	0.7884	0.065*
C7	0.25784 (11)	0.15403 (18)	0.67342 (11)	0.0608 (6)
H7A	0.2256	0.1348	0.6392	0.073*
H7B	0.2857	0.0893	0.6828	0.073*
C8	0.30456 (13)	0.2463 (3)	0.65010 (14)	0.0890 (8)
H8A	0.2773	0.3106	0.6409	0.133*
H8B	0.3282	0.2233	0.6115	0.133*
H8C	0.3379	0.2634	0.6831	0.133*
C9	0.15149 (10)	0.21488 (15)	0.72709 (10)	0.0457 (5)
C10	0.04705 (11)	0.17912 (18)	0.66673 (10)	0.0540 (5)
C11	0.01366 (10)	0.26259 (18)	0.69650 (11)	0.0555 (5)
C12	0.04016 (10)	0.30390 (16)	0.76091 (10)	0.0515 (5)
H12	0.0249	0.3805	0.7660	0.062*
C13	0.11850 (9)	0.30414 (15)	0.75527 (10)	0.0473 (5)
C14	0.12560 (12)	0.02347 (17)	0.68983 (12)	0.0629 (6)
H14A	0.1431	0.0043	0.6478	0.094*
H14B	0.0841	−0.0175	0.6983	0.094*
H14C	0.1596	0.0060	0.7221	0.094*
C15	−0.04783 (12)	0.3063 (2)	0.66890 (13)	0.0663 (6)
C16	0.01488 (10)	0.23895 (18)	0.81946 (11)	0.0551 (5)
C17	−0.01453 (13)	0.1358 (2)	0.81419 (14)	0.0727 (7)
H17	−0.0206	0.1046	0.7734	0.087*
C18	−0.03510 (15)	0.0781 (2)	0.86844 (16)	0.0910 (9)
H18	−0.0544	0.0082	0.8638	0.109*
C19	−0.02752 (15)	0.1221 (3)	0.92841 (17)	0.0951 (9)
H19	−0.0416	0.0830	0.9649	0.114*
C20	0.00120 (15)	0.2249 (3)	0.93454 (15)	0.0975 (10)
H20	0.0067	0.2558	0.9755	0.117*
C21	0.02208 (13)	0.2832 (2)	0.88048 (13)	0.0784 (7)
H21	0.0412	0.3531	0.8854	0.094*
Cl1	0.13433 (5)	0.14060 (7)	1.04868 (3)	0.1000 (3)
N1	0.19380 (11)	0.25445 (17)	0.95814 (10)	0.0710 (6)
N2	0.21881 (8)	0.18511 (13)	0.73179 (8)	0.0486 (4)
N3	0.11034 (8)	0.14244 (13)	0.69193 (8)	0.0491 (4)
N4	0.02386 (10)	0.12143 (17)	0.61498 (10)	0.0750 (6)
H4A	−0.0156	0.1370	0.5981	0.090*
H4B	0.0486	0.0692	0.5989	0.090*
N5	−0.09771 (11)	0.34154 (19)	0.64678 (13)	0.0927 (7)
N6	0.15343 (9)	0.40156 (14)	0.77108 (9)	0.0568 (5)
O1	0.12139 (9)	0.47446 (13)	0.80126 (9)	0.0812 (5)
O2	0.21474 (8)	0.41614 (12)	0.75479 (9)	0.0703 (5)
C22	0.1322 (6)	−0.1213 (7)	0.4967 (5)	0.147 (4)	0.57
H22A	0.1746	−0.1413	0.5178	0.220*	0.57
H22B	0.1263	−0.1656	0.4585	0.220*	0.57
H22C	0.0941	−0.1334	0.5256	0.220*	0.57
C23	0.1345 (8)	−0.0106 (7)	0.4793 (5)	0.194 (6)	0.57
H23A	0.0942	0.0043	0.4528	0.233*	0.57
H23B	0.1747	−0.0004	0.4519	0.233*	0.57
O3	0.1370 (7)	0.0705 (9)	0.5276 (6)	0.145 (5)	0.57
H3A	0.1532	0.1222	0.5069	0.218*	0.57
C22'	0.1377 (5)	−0.0766 (13)	0.4602 (5)	0.113 (3)	0.43
H22D	0.0896	−0.0859	0.4701	0.169*	0.43
H22E	0.1581	−0.1473	0.4513	0.169*	0.43
H22F	0.1425	−0.0298	0.4229	0.169*	0.43
C23'	0.1723 (4)	−0.0269 (7)	0.5146 (4)	0.094 (2)	0.43
H23C	0.1732	−0.0788	0.5503	0.113*	0.43
H23D	0.2198	−0.0105	0.5028	0.113*	0.43
O3'	0.1403 (5)	0.0683 (7)	0.5341 (6)	0.085 (3)	0.43
H3B	0.1193	0.0955	0.5035	0.127*	0.43

	U11	U22	U33	U12	U13	U23
C1	0.0703 (15)	0.0707 (16)	0.0606 (14)	−0.0110 (12)	0.0025 (12)	0.0082 (12)
C2	0.0759 (15)	0.0581 (14)	0.0690 (16)	−0.0160 (12)	−0.0023 (13)	0.0120 (12)
C3	0.0652 (14)	0.0515 (12)	0.0616 (14)	−0.0049 (10)	−0.0046 (11)	0.0034 (11)
C4	0.0448 (11)	0.0496 (12)	0.0582 (13)	−0.0018 (9)	−0.0067 (9)	0.0043 (10)
C5	0.0669 (14)	0.0556 (13)	0.0683 (16)	−0.0134 (11)	0.0021 (12)	0.0053 (12)
C6	0.0416 (11)	0.0535 (12)	0.0665 (14)	−0.0009 (9)	−0.0016 (10)	0.0037 (10)
C7	0.0543 (12)	0.0631 (14)	0.0651 (14)	0.0088 (10)	0.0134 (11)	0.0066 (11)
C8	0.0765 (17)	0.0963 (19)	0.094 (2)	−0.0013 (15)	0.0331 (15)	0.0180 (16)
C9	0.0440 (11)	0.0428 (11)	0.0505 (11)	−0.0034 (9)	0.0030 (9)	0.0091 (9)
C10	0.0472 (11)	0.0586 (13)	0.0563 (13)	−0.0054 (10)	−0.0024 (10)	0.0052 (11)
C11	0.0430 (11)	0.0554 (12)	0.0682 (14)	0.0019 (10)	−0.0014 (10)	0.0085 (11)
C12	0.0435 (11)	0.0430 (11)	0.0682 (14)	0.0065 (9)	0.0034 (10)	0.0016 (10)
C13	0.0448 (11)	0.0389 (10)	0.0584 (12)	−0.0016 (9)	0.0009 (9)	0.0053 (9)
C14	0.0681 (14)	0.0443 (12)	0.0764 (16)	−0.0008 (10)	−0.0046 (12)	−0.0002 (11)
C15	0.0502 (13)	0.0630 (14)	0.0856 (17)	−0.0020 (11)	−0.0027 (12)	0.0091 (13)
C16	0.0394 (10)	0.0570 (13)	0.0690 (14)	0.0056 (10)	0.0088 (10)	0.0011 (11)
C17	0.0740 (15)	0.0651 (15)	0.0790 (17)	−0.0060 (13)	0.0211 (13)	0.0025 (13)
C18	0.094 (2)	0.0777 (18)	0.102 (2)	−0.0085 (15)	0.0348 (18)	0.0158 (17)
C19	0.0780 (19)	0.118 (3)	0.090 (2)	0.0036 (18)	0.0234 (16)	0.033 (2)
C20	0.087 (2)	0.141 (3)	0.0646 (18)	−0.006 (2)	0.0106 (15)	0.0001 (19)
C21	0.0729 (16)	0.0889 (19)	0.0735 (18)	−0.0101 (14)	0.0092 (14)	−0.0073 (15)
Cl1	0.1254 (7)	0.1083 (6)	0.0663 (5)	−0.0273 (5)	0.0183 (4)	0.0100 (4)
N1	0.0846 (14)	0.0667 (13)	0.0618 (13)	−0.0142 (11)	0.0057 (10)	−0.0010 (10)
N2	0.0411 (9)	0.0498 (9)	0.0550 (10)	0.0011 (7)	0.0036 (8)	0.0046 (8)
N3	0.0455 (9)	0.0430 (9)	0.0588 (10)	0.0013 (7)	−0.0006 (8)	0.0022 (8)
N4	0.0625 (12)	0.0837 (14)	0.0787 (14)	0.0041 (10)	−0.0180 (10)	−0.0155 (12)
N5	0.0568 (13)	0.0909 (16)	0.130 (2)	0.0106 (11)	−0.0179 (13)	0.0186 (15)
N6	0.0557 (11)	0.0431 (10)	0.0715 (12)	−0.0019 (9)	0.0003 (9)	0.0057 (9)
O1	0.0788 (11)	0.0533 (10)	0.1115 (14)	−0.0030 (9)	0.0099 (10)	−0.0224 (10)
O2	0.0534 (9)	0.0533 (9)	0.1042 (13)	−0.0117 (7)	0.0058 (9)	0.0071 (9)
C22	0.203 (10)	0.110 (7)	0.128 (8)	−0.023 (6)	−0.051 (7)	0.017 (5)
C23	0.363 (19)	0.097 (7)	0.122 (8)	0.046 (9)	−0.026 (10)	−0.009 (6)
O3	0.219 (11)	0.122 (8)	0.095 (6)	0.048 (7)	0.036 (6)	−0.014 (6)
C22'	0.099 (6)	0.134 (10)	0.105 (8)	−0.003 (7)	0.013 (6)	−0.021 (7)
C23'	0.099 (5)	0.105 (7)	0.077 (5)	0.040 (5)	−0.010 (4)	0.013 (5)
O3'	0.105 (6)	0.055 (5)	0.093 (7)	−0.001 (5)	0.037 (5)	0.016 (5)

C1—N1	1.309 (3)	C14—H14B	0.9600
C1—C2	1.374 (3)	C14—H14C	0.9600
C1—Cl1	1.747 (3)	C15—N5	1.149 (3)
C2—C3	1.368 (3)	C16—C21	1.376 (3)
C2—H2	0.9300	C16—C17	1.377 (3)
C3—C4	1.385 (3)	C17—C18	1.379 (4)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.369 (3)	C18—C19	1.356 (4)
C4—C6	1.498 (3)	C18—H18	0.9300
C5—N1	1.345 (3)	C19—C20	1.370 (5)
C5—H5	0.9300	C19—H19	0.9300
C6—N2	1.467 (3)	C20—C21	1.381 (4)
C6—H6A	0.9700	C20—H20	0.9300
C6—H6B	0.9700	C21—H21	0.9300
C7—N2	1.471 (3)	N4—H4A	0.8600
C7—C8	1.516 (3)	N4—H4B	0.8600
C7—H7A	0.9700	N6—O2	1.245 (2)
C7—H7B	0.9700	N6—O1	1.246 (2)
C8—H8A	0.9600	C22—C23	1.388 (8)
C8—H8B	0.9600	C22—H22A	0.9600
C8—H8C	0.9600	C22—H22B	0.9600
C9—N2	1.354 (2)	C22—H22C	0.9600
C9—C13	1.384 (3)	C23—O3	1.400 (9)
C9—N3	1.389 (2)	C23—H23A	0.9700
C10—C11	1.348 (3)	C23—H23B	0.9700
C10—N4	1.353 (3)	O3—H3A	0.8200
C10—N3	1.402 (3)	C22'—C23'	1.439 (8)
C11—C15	1.420 (3)	C22'—H22D	0.9600
C11—C12	1.510 (3)	C22'—H22E	0.9600
C12—C13	1.519 (3)	C22'—H22F	0.9600
C12—C16	1.523 (3)	C23'—O3'	1.370 (8)
C12—H12	0.9800	C23'—H23C	0.9700
C13—N6	1.398 (3)	C23'—H23D	0.9700
C14—N3	1.472 (3)	O3'—H3A	0.8975
C14—H14A	0.9600	O3'—H3B	0.8200
N1—C1—C2	125.0 (2)	H14A—C14—H14C	109.5
N1—C1—Cl1	115.25 (19)	H14B—C14—H14C	109.5
C2—C1—Cl1	119.72 (19)	N5—C15—C11	179.7 (3)
C3—C2—C1	117.2 (2)	C21—C16—C17	117.9 (2)
C3—C2—H2	121.4	C21—C16—C12	119.5 (2)
C1—C2—H2	121.4	C17—C16—C12	122.6 (2)
C2—C3—C4	120.4 (2)	C16—C17—C18	121.0 (3)
C2—C3—H3	119.8	C16—C17—H17	119.5
C4—C3—H3	119.8	C18—C17—H17	119.5
C5—C4—C3	116.5 (2)	C19—C18—C17	120.8 (3)
C5—C4—C6	120.69 (19)	C19—C18—H18	119.6
C3—C4—C6	122.7 (2)	C17—C18—H18	119.6
N1—C5—C4	124.6 (2)	C18—C19—C20	119.0 (3)
N1—C5—H5	117.7	C18—C19—H19	120.5
C4—C5—H5	117.7	C20—C19—H19	120.5
N2—C6—C4	113.92 (16)	C19—C20—C21	120.6 (3)
N2—C6—H6A	108.8	C19—C20—H20	119.7
C4—C6—H6A	108.8	C21—C20—H20	119.7
N2—C6—H6B	108.8	C16—C21—C20	120.7 (3)
C4—C6—H6B	108.8	C16—C21—H21	119.6
H6A—C6—H6B	107.7	C20—C21—H21	119.6
N2—C7—C8	112.2 (2)	C1—N1—C5	116.1 (2)
N2—C7—H7A	109.2	C9—N2—C6	122.86 (17)
C8—C7—H7A	109.2	C9—N2—C7	120.18 (18)
N2—C7—H7B	109.2	C6—N2—C7	115.36 (15)
C8—C7—H7B	109.2	C9—N3—C10	119.57 (16)
H7A—C7—H7B	107.9	C9—N3—C14	121.28 (16)
C7—C8—H8A	109.5	C10—N3—C14	118.32 (17)
C7—C8—H8B	109.5	C10—N4—H4A	120.0
H8A—C8—H8B	109.5	C10—N4—H4B	120.0
C7—C8—H8C	109.5	H4A—N4—H4B	120.0
H8A—C8—H8C	109.5	O2—N6—O1	120.54 (17)
H8B—C8—H8C	109.5	O2—N6—C13	121.09 (18)
N2—C9—C13	128.39 (18)	O1—N6—C13	118.36 (17)
N2—C9—N3	114.80 (17)	C22—C23—O3	119.7 (11)
C13—C9—N3	116.72 (17)	C22—C23—H23A	107.4
C11—C10—N4	126.1 (2)	O3—C23—H23A	107.4
C11—C10—N3	119.12 (19)	C22—C23—H23B	107.4
N4—C10—N3	114.74 (19)	O3—C23—H23B	107.4
C10—C11—C15	119.8 (2)	H23A—C23—H23B	106.9
C10—C11—C12	119.17 (18)	C23—O3—H3A	100.2
C15—C11—C12	120.9 (2)	C23'—C22'—H22D	109.5
C11—C12—C13	105.76 (17)	C23'—C22'—H22E	109.5
C11—C12—C16	114.75 (17)	H22D—C22'—H22E	109.5
C13—C12—C16	112.45 (17)	C23'—C22'—H22F	109.5
C11—C12—H12	107.9	H22D—C22'—H22F	109.5
C13—C12—H12	107.9	H22E—C22'—H22F	109.5
C16—C12—H12	107.9	O3'—C23'—C22'	111.9 (11)
C9—C13—N6	122.37 (17)	O3'—C23'—H23C	109.2
C9—C13—C12	119.35 (17)	C22'—C23'—H23C	109.2
N6—C13—C12	117.72 (17)	O3'—C23'—H23D	109.2
N3—C14—H14A	109.5	C22'—C23'—H23D	109.2
N3—C14—H14B	109.5	H23C—C23'—H23D	107.9
H14A—C14—H14B	109.5	C23'—O3'—H3A	107.5
N3—C14—H14C	109.5	C23'—O3'—H3B	109.5
N1—C1—C2—C3	2.3 (4)	C12—C16—C17—C18	178.2 (2)
Cl1—C1—C2—C3	−177.31 (18)	C16—C17—C18—C19	0.7 (4)
C1—C2—C3—C4	−0.4 (3)	C17—C18—C19—C20	−0.2 (5)
C2—C3—C4—C5	−1.5 (3)	C18—C19—C20—C21	0.1 (5)
C2—C3—C4—C6	174.9 (2)	C17—C16—C21—C20	0.8 (4)
C3—C4—C5—N1	1.9 (3)	C12—C16—C21—C20	−178.4 (2)
C6—C4—C5—N1	−174.6 (2)	C19—C20—C21—C16	−0.4 (4)
C5—C4—C6—N2	−127.6 (2)	C2—C1—N1—C5	−2.1 (4)
C3—C4—C6—N2	56.2 (3)	Cl1—C1—N1—C5	177.59 (17)
N4—C10—C11—C15	−8.0 (3)	C4—C5—N1—C1	−0.1 (4)
N3—C10—C11—C15	175.28 (19)	C13—C9—N2—C6	31.1 (3)
N4—C10—C11—C12	168.5 (2)	N3—C9—N2—C6	−145.33 (18)
N3—C10—C11—C12	−8.2 (3)	C13—C9—N2—C7	−133.8 (2)
C10—C11—C12—C13	40.0 (2)	N3—C9—N2—C7	49.8 (2)
C15—C11—C12—C13	−143.46 (19)	C4—C6—N2—C9	40.7 (3)
C10—C11—C12—C16	−84.5 (2)	C4—C6—N2—C7	−153.71 (17)
C15—C11—C12—C16	92.0 (2)	C8—C7—N2—C9	101.8 (2)
N2—C9—C13—N6	27.3 (3)	C8—C7—N2—C6	−64.2 (2)
N3—C9—C13—N6	−156.32 (18)	N2—C9—N3—C10	−160.22 (17)
N2—C9—C13—C12	−161.53 (19)	C13—C9—N3—C10	22.9 (3)
N3—C9—C13—C12	14.9 (3)	N2—C9—N3—C14	30.4 (3)
C11—C12—C13—C9	−43.8 (2)	C13—C9—N3—C14	−146.51 (19)
C16—C12—C13—C9	82.2 (2)	C11—C10—N3—C9	−26.8 (3)
C11—C12—C13—N6	127.84 (19)	N4—C10—N3—C9	156.08 (19)
C16—C12—C13—N6	−106.2 (2)	C11—C10—N3—C14	142.9 (2)
C11—C12—C16—C21	−164.9 (2)	N4—C10—N3—C14	−34.2 (3)
C13—C12—C16—C21	74.1 (3)	C9—C13—N6—O2	6.9 (3)
C11—C12—C16—C17	15.9 (3)	C12—C13—N6—O2	−164.43 (18)
C13—C12—C16—C17	−105.0 (2)	C9—C13—N6—O1	−174.0 (2)
C21—C16—C17—C18	−1.0 (4)	C12—C13—N6—O1	14.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N1i	0.82	1.97	2.785 (13)	179
N4—H4B···O3	0.86	2.26	2.902 (11)	132
C6—H6A···O2	0.97	2.13	2.783 (3)	124
C7—H7B···O2ii	0.97	2.57	3.378 (3)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯N1i	0.82	1.97	2.785 (13)	179
N4—H4B⋯O3	0.86	2.26	2.902 (11)	132
C6—H6A⋯O2	0.97	2.13	2.783 (3)	124
C7—H7B⋯O2ii	0.97	2.57	3.378 (3)	141

Symmetry codes: (i) ; (ii) .