2-Fluoro-N'-[(2-meth-oxy-naphthalen-1-yl)methyl-idene]benzohydrazide.

The asymmetric unit of the title compound, C(19)H(15)FN(2)O(2), contains two mol-ecules, A and B, in which the dihedral angles between the ring systems are 46.4 (2) and 17.24 (14)°, respectively. In the crystal, mol-ecules are linked into [010] chains of alternating A and B species by N-H⋯O hydrogen bonds.

Related literature

For a related structure and background to hydrazones, see: Li (2011 ▶). For related structures, see: Qiu et al. (2006 ▶); Yang & Guo (2006 ▶); Yang (2006 ▶).

Experimental

Crystal data

C19H15FN2O2

M = 322.33

Monoclinic,

a = 9.462 (2) Å

b = 17.030 (3) Å

c = 20.470 (2) Å

β = 96.575 (2)°

V = 3276.9 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.18 × 0.18 × 0.17 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.983, T max = 0.984

19271 measured reflections

6420 independent reflections

3070 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.188

S = 1.01

6420 reflections

441 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.53 e Å−3

Δρmin = −0.30 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812011580/hb6672sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011580/hb6672Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812011580/hb6672Isup3.cml

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

C19H15FN2O2	F(000) = 1344
Mr = 322.33	Dx = 1.307 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2255 reflections
a = 9.462 (2) Å	θ = 2.4–24.5°
b = 17.030 (3) Å	µ = 0.09 mm−1
c = 20.470 (2) Å	T = 298 K
β = 96.575 (2)°	Cut from needle, colorless
V = 3276.9 (10) Å3	0.18 × 0.18 × 0.17 mm
Z = 8

Bruker SMART CCD diffractometer	6420 independent reflections
Radiation source: fine-focus sealed tube	3070 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.983, Tmax = 0.984	k = −20→20
19271 measured reflections	l = −18→25

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.188	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0767P)2 + 0.7482P] where P = (Fo2 + 2Fc2)/3
6420 reflections	(Δ/σ)max < 0.001
441 parameters	Δρmax = 0.53 e Å−3
2 restraints	Δρmin = −0.30 e Å−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
F1	−0.0022 (4)	0.3477 (2)	0.06984 (17)	0.1590 (14)
F2	1.3946 (2)	0.57294 (11)	0.16914 (12)	0.0780 (7)
H1	−0.008 (4)	0.4855 (11)	0.2092 (17)	0.080*
H3	1.086 (4)	0.7327 (10)	0.2401 (18)	0.080*
N1	−0.0394 (3)	0.43870 (15)	0.22248 (13)	0.0457 (7)
N2	0.0044 (3)	0.41427 (15)	0.28601 (13)	0.0469 (7)
N3	1.0565 (3)	0.68423 (14)	0.22805 (13)	0.0468 (7)
N4	0.9273 (3)	0.65685 (15)	0.24414 (13)	0.0463 (7)
O1	−0.1478 (3)	0.32290 (13)	0.19477 (12)	0.0626 (7)
O2	0.1075 (3)	0.59232 (16)	0.39855 (13)	0.0798 (8)
O3	1.0985 (2)	0.57402 (13)	0.17140 (11)	0.0580 (6)
O4	0.7134 (3)	0.83626 (14)	0.29575 (15)	0.0837 (9)
C1	−0.1047 (6)	0.3992 (3)	0.0618 (3)	0.0899 (14)
C2	−0.1593 (4)	0.4240 (2)	0.11484 (17)	0.0554 (9)
C3	−0.2676 (6)	0.4823 (3)	0.1082 (3)	0.1151 (19)
H3A	−0.3091	0.5027	0.1436	0.138*
C4	−0.3049 (8)	0.5056 (3)	0.0437 (4)	0.153 (3)
H4	−0.3757	0.5434	0.0362	0.183*
C5	−0.2457 (11)	0.4774 (4)	−0.0104 (4)	0.167 (4)
H5	−0.2777	0.4956	−0.0524	0.200*
C6	−0.1433 (8)	0.4244 (4)	−0.0018 (2)	0.132 (3)
H6	−0.0995	0.4050	−0.0369	0.158*
C7	−0.1146 (3)	0.38962 (19)	0.18080 (15)	0.0427 (8)
C8	0.0679 (3)	0.4674 (2)	0.32235 (16)	0.0498 (8)
H8	0.0799	0.5165	0.3039	0.060*
C9	0.1224 (3)	0.4555 (2)	0.39083 (16)	0.0502 (9)
C10	0.1416 (4)	0.5229 (2)	0.42919 (18)	0.0646 (10)
C11	0.1938 (6)	0.5182 (3)	0.4958 (2)	0.1005 (16)
H11	0.2067	0.5637	0.5208	0.121*
C12	0.2255 (6)	0.4478 (3)	0.5238 (2)	0.1048 (17)
H12	0.2594	0.4457	0.5683	0.126*
C13	0.2088 (4)	0.3779 (3)	0.48811 (18)	0.0711 (11)
C14	0.2415 (5)	0.3050 (3)	0.5180 (2)	0.0904 (14)
H14	0.2767	0.3035	0.5623	0.109*
C15	0.2231 (4)	0.2367 (3)	0.4841 (2)	0.0800 (13)
H15	0.2438	0.1889	0.5049	0.096*
C16	0.1727 (4)	0.2394 (2)	0.4175 (2)	0.0681 (11)
H16	0.1596	0.1929	0.3938	0.082*
C17	0.1425 (3)	0.3090 (2)	0.38666 (18)	0.0556 (9)
H17	0.1114	0.3091	0.3419	0.067*
C18	0.1572 (3)	0.3809 (2)	0.42067 (16)	0.0517 (9)
C19	0.1272 (6)	0.6641 (2)	0.4349 (2)	0.1031 (16)
H19A	0.0739	0.6621	0.4720	0.155*
H19B	0.0947	0.7073	0.4071	0.155*
H19C	0.2263	0.6708	0.4499	0.155*
C20	1.3748 (4)	0.64862 (18)	0.15306 (17)	0.0503 (9)
C21	1.2493 (3)	0.68480 (17)	0.16285 (15)	0.0407 (7)
C22	1.2363 (4)	0.76311 (19)	0.14472 (17)	0.0535 (9)
H22	1.1536	0.7902	0.1510	0.064*
C23	1.3431 (4)	0.8014 (2)	0.11767 (19)	0.0644 (10)
H23	1.3308	0.8534	0.1046	0.077*
C24	1.4673 (4)	0.7636 (2)	0.1098 (2)	0.0735 (12)
H24	1.5400	0.7901	0.0921	0.088*
C25	1.4845 (4)	0.6864 (2)	0.1280 (2)	0.0708 (11)
H25	1.5690	0.6601	0.1233	0.085*
C26	1.1294 (3)	0.64171 (18)	0.18800 (15)	0.0424 (8)
C27	0.8576 (3)	0.70852 (19)	0.27226 (15)	0.0461 (8)
H27	0.9017	0.7568	0.2811	0.055*
C28	0.7151 (3)	0.69900 (18)	0.29183 (14)	0.0419 (7)
C29	0.6442 (4)	0.7680 (2)	0.30429 (17)	0.0538 (9)
C30	0.5059 (4)	0.7667 (2)	0.32251 (19)	0.0678 (11)
H30	0.4593	0.8136	0.3295	0.081*
C31	0.4411 (4)	0.6978 (2)	0.32980 (19)	0.0681 (11)
H31	0.3492	0.6976	0.3418	0.082*
C32	0.5078 (3)	0.6258 (2)	0.31977 (17)	0.0549 (9)
C33	0.4409 (4)	0.5537 (3)	0.3293 (2)	0.0742 (12)
H33	0.3506	0.5536	0.3431	0.089*
C34	0.5048 (4)	0.4843 (2)	0.3190 (2)	0.0772 (12)
H34	0.4589	0.4372	0.3257	0.093*
C35	0.6399 (4)	0.4842 (2)	0.29817 (19)	0.0663 (10)
H35	0.6836	0.4367	0.2904	0.080*
C36	0.7081 (4)	0.55235 (18)	0.28913 (17)	0.0534 (9)
H36	0.7987	0.5508	0.2757	0.064*
C37	0.6458 (3)	0.62534 (18)	0.29945 (14)	0.0422 (8)
C38	0.6786 (5)	0.9035 (2)	0.3292 (2)	0.0879 (14)
H38A	0.5837	0.9197	0.3132	0.132*
H38B	0.7442	0.9447	0.3220	0.132*
H38C	0.6838	0.8923	0.3754	0.132*

	U11	U22	U33	U12	U13	U23
F1	0.181 (4)	0.188 (3)	0.119 (3)	0.030 (3)	0.062 (3)	−0.018 (2)
F2	0.0723 (14)	0.0502 (13)	0.1137 (19)	0.0092 (10)	0.0203 (13)	0.0088 (12)
N1	0.0481 (16)	0.0476 (17)	0.0404 (16)	−0.0057 (13)	0.0003 (13)	0.0044 (14)
N2	0.0487 (16)	0.0549 (17)	0.0366 (16)	−0.0028 (13)	0.0026 (13)	0.0052 (14)
N3	0.0456 (16)	0.0439 (16)	0.0534 (17)	−0.0090 (13)	0.0170 (13)	−0.0083 (14)
N4	0.0436 (16)	0.0489 (16)	0.0489 (17)	−0.0040 (13)	0.0160 (13)	−0.0021 (13)
O1	0.0756 (17)	0.0448 (14)	0.0638 (16)	−0.0116 (12)	−0.0074 (13)	0.0118 (12)
O2	0.112 (2)	0.0629 (18)	0.0635 (18)	−0.0032 (15)	0.0045 (16)	−0.0105 (15)
O3	0.0672 (15)	0.0424 (14)	0.0685 (16)	−0.0146 (11)	0.0257 (13)	−0.0102 (12)
O4	0.0845 (19)	0.0444 (15)	0.130 (3)	0.0030 (14)	0.0466 (18)	−0.0075 (15)
C1	0.106 (4)	0.081 (3)	0.082 (4)	0.007 (3)	0.008 (3)	0.003 (3)
C2	0.075 (2)	0.050 (2)	0.039 (2)	−0.0166 (19)	−0.0042 (19)	−0.0007 (17)
C3	0.131 (4)	0.092 (3)	0.105 (4)	0.018 (3)	−0.061 (3)	0.053 (3)
C4	0.221 (8)	0.092 (4)	0.125 (5)	0.026 (4)	−0.071 (6)	0.010 (4)
C5	0.278 (11)	0.105 (6)	0.092 (5)	−0.049 (6)	−0.088 (6)	0.040 (4)
C6	0.221 (8)	0.138 (6)	0.035 (3)	−0.055 (5)	0.008 (4)	0.001 (3)
C7	0.0421 (18)	0.0409 (19)	0.044 (2)	0.0030 (15)	0.0016 (15)	0.0016 (16)
C8	0.049 (2)	0.055 (2)	0.045 (2)	−0.0051 (17)	0.0051 (16)	0.0006 (17)
C9	0.0438 (19)	0.069 (2)	0.038 (2)	−0.0102 (17)	0.0039 (15)	−0.0053 (18)
C10	0.079 (3)	0.071 (3)	0.044 (2)	−0.012 (2)	0.0066 (19)	−0.003 (2)
C11	0.154 (5)	0.097 (4)	0.047 (3)	−0.019 (3)	−0.005 (3)	−0.019 (3)
C12	0.161 (5)	0.105 (4)	0.044 (3)	−0.014 (4)	−0.012 (3)	0.000 (3)
C13	0.086 (3)	0.088 (3)	0.038 (2)	−0.007 (2)	0.001 (2)	0.010 (2)
C14	0.109 (4)	0.111 (4)	0.050 (3)	0.001 (3)	0.002 (2)	0.020 (3)
C15	0.077 (3)	0.092 (3)	0.072 (3)	0.008 (2)	0.012 (2)	0.029 (3)
C16	0.053 (2)	0.074 (3)	0.077 (3)	0.0002 (19)	0.005 (2)	0.014 (2)
C17	0.049 (2)	0.065 (2)	0.052 (2)	−0.0016 (18)	0.0004 (17)	0.008 (2)
C18	0.0451 (19)	0.069 (3)	0.041 (2)	−0.0073 (17)	0.0056 (15)	0.0037 (19)
C19	0.145 (5)	0.071 (3)	0.098 (4)	−0.012 (3)	0.033 (3)	−0.027 (3)
C20	0.055 (2)	0.0336 (19)	0.063 (2)	0.0042 (16)	0.0136 (18)	0.0009 (16)
C21	0.0411 (18)	0.0403 (19)	0.0413 (18)	−0.0021 (14)	0.0076 (14)	−0.0017 (15)
C22	0.054 (2)	0.045 (2)	0.064 (2)	0.0011 (16)	0.0148 (18)	0.0060 (17)
C23	0.065 (2)	0.049 (2)	0.082 (3)	−0.0026 (19)	0.018 (2)	0.0143 (19)
C24	0.062 (3)	0.061 (3)	0.104 (3)	−0.008 (2)	0.039 (2)	0.006 (2)
C25	0.052 (2)	0.065 (3)	0.101 (3)	0.0006 (19)	0.032 (2)	0.000 (2)
C26	0.0468 (19)	0.0384 (19)	0.0424 (19)	−0.0009 (15)	0.0059 (15)	0.0013 (15)
C27	0.0460 (19)	0.0466 (19)	0.046 (2)	−0.0071 (16)	0.0083 (16)	0.0024 (16)
C28	0.0410 (18)	0.0499 (19)	0.0355 (17)	−0.0009 (15)	0.0079 (14)	−0.0034 (15)
C29	0.055 (2)	0.048 (2)	0.060 (2)	0.0018 (18)	0.0138 (18)	−0.0034 (18)
C30	0.057 (2)	0.064 (3)	0.084 (3)	0.017 (2)	0.017 (2)	−0.007 (2)
C31	0.047 (2)	0.081 (3)	0.079 (3)	0.004 (2)	0.020 (2)	−0.002 (2)
C32	0.043 (2)	0.066 (2)	0.057 (2)	−0.0038 (18)	0.0125 (16)	0.0014 (19)
C33	0.053 (2)	0.091 (3)	0.082 (3)	−0.012 (2)	0.023 (2)	0.003 (2)
C34	0.073 (3)	0.068 (3)	0.094 (3)	−0.024 (2)	0.023 (2)	0.003 (2)
C35	0.071 (3)	0.055 (2)	0.076 (3)	−0.006 (2)	0.023 (2)	0.002 (2)
C36	0.054 (2)	0.048 (2)	0.060 (2)	−0.0031 (17)	0.0193 (18)	−0.0012 (17)
C37	0.0404 (18)	0.051 (2)	0.0354 (18)	−0.0016 (15)	0.0047 (14)	0.0019 (15)
C38	0.107 (4)	0.054 (2)	0.104 (4)	0.006 (2)	0.016 (3)	−0.015 (2)

F1—C1	1.304 (5)	C15—H15	0.9300
F2—C20	1.338 (3)	C16—C17	1.357 (5)
N1—C7	1.340 (4)	C16—H16	0.9300
N1—N2	1.383 (3)	C17—C18	1.407 (5)
N1—H1	0.903 (10)	C17—H17	0.9300
N2—C8	1.277 (4)	C19—H19A	0.9600
N3—C26	1.342 (4)	C19—H19B	0.9600
N3—N4	1.383 (3)	C19—H19C	0.9600
N3—H3	0.897 (10)	C20—C25	1.370 (5)
N4—C27	1.276 (4)	C20—C21	1.374 (4)
O1—C7	1.221 (3)	C21—C22	1.386 (4)
O2—C10	1.359 (4)	C21—C26	1.491 (4)
O2—C19	1.431 (4)	C22—C23	1.371 (4)
O3—C26	1.228 (3)	C22—H22	0.9300
O4—C29	1.356 (4)	C23—C24	1.366 (5)
O4—C38	1.392 (4)	C23—H23	0.9300
C1—C2	1.325 (6)	C24—C25	1.371 (5)
C1—C6	1.379 (7)	C24—H24	0.9300
C2—C3	1.421 (6)	C25—H25	0.9300
C2—C7	1.488 (4)	C27—C28	1.458 (4)
C3—C4	1.385 (8)	C27—H27	0.9300
C3—H3A	0.9300	C28—C29	1.390 (4)
C4—C5	1.383 (10)	C28—C37	1.432 (4)
C4—H4	0.9300	C29—C30	1.402 (5)
C5—C6	1.321 (9)	C30—C31	1.342 (5)
C5—H5	0.9300	C30—H30	0.9300
C6—H6	0.9300	C31—C32	1.404 (5)
C8—C9	1.451 (4)	C31—H31	0.9300
C8—H8	0.9300	C32—C33	1.406 (5)
C9—C10	1.392 (5)	C32—C37	1.415 (4)
C9—C18	1.431 (5)	C33—C34	1.355 (5)
C10—C11	1.398 (5)	C33—H33	0.9300
C11—C12	1.348 (6)	C34—C35	1.393 (5)
C11—H11	0.9300	C34—H34	0.9300
C12—C13	1.396 (6)	C35—C36	1.351 (4)
C12—H12	0.9300	C35—H35	0.9300
C13—C14	1.403 (5)	C36—C37	1.402 (4)
C13—C18	1.412 (5)	C36—H36	0.9300
C14—C15	1.355 (6)	C38—H38A	0.9600
C14—H14	0.9300	C38—H38B	0.9600
C15—C16	1.392 (6)	C38—H38C	0.9600
C7—N1—N2	119.4 (3)	O2—C19—H19B	109.5
C7—N1—H1	122 (2)	H19A—C19—H19B	109.5
N2—N1—H1	118 (2)	O2—C19—H19C	109.5
C8—N2—N1	113.9 (3)	H19A—C19—H19C	109.5
C26—N3—N4	119.6 (2)	H19B—C19—H19C	109.5
C26—N3—H3	120 (2)	F2—C20—C25	117.0 (3)
N4—N3—H3	120 (2)	F2—C20—C21	119.7 (3)
C27—N4—N3	113.1 (3)	C25—C20—C21	123.3 (3)
C10—O2—C19	119.5 (3)	C20—C21—C22	116.4 (3)
C29—O4—C38	119.8 (3)	C20—C21—C26	122.3 (3)
F1—C1—C2	117.7 (4)	C22—C21—C26	121.2 (3)
F1—C1—C6	116.3 (6)	C23—C22—C21	121.2 (3)
C2—C1—C6	126.0 (5)	C23—C22—H22	119.4
C1—C2—C3	119.3 (4)	C21—C22—H22	119.4
C1—C2—C7	121.4 (4)	C24—C23—C22	120.5 (3)
C3—C2—C7	119.2 (4)	C24—C23—H23	119.7
C4—C3—C2	113.2 (6)	C22—C23—H23	119.7
C4—C3—H3A	123.4	C23—C24—C25	119.8 (3)
C2—C3—H3A	123.4	C23—C24—H24	120.1
C5—C4—C3	125.6 (7)	C25—C24—H24	120.1
C5—C4—H4	117.2	C20—C25—C24	118.7 (3)
C3—C4—H4	117.2	C20—C25—H25	120.6
C6—C5—C4	119.2 (6)	C24—C25—H25	120.6
C6—C5—H5	120.4	O3—C26—N3	123.6 (3)
C4—C5—H5	120.4	O3—C26—C21	122.2 (3)
C5—C6—C1	116.8 (6)	N3—C26—C21	114.2 (3)
C5—C6—H6	121.6	N4—C27—C28	126.1 (3)
C1—C6—H6	121.6	N4—C27—H27	116.9
O1—C7—N1	124.3 (3)	C28—C27—H27	116.9
O1—C7—C2	121.7 (3)	C29—C28—C37	118.9 (3)
N1—C7—C2	114.0 (3)	C29—C28—C27	115.9 (3)
N2—C8—C9	123.7 (3)	C37—C28—C27	125.2 (3)
N2—C8—H8	118.1	O4—C29—C28	116.8 (3)
C9—C8—H8	118.1	O4—C29—C30	121.7 (3)
C10—C9—C18	118.9 (3)	C28—C29—C30	121.4 (3)
C10—C9—C8	116.0 (3)	C31—C30—C29	119.7 (3)
C18—C9—C8	125.1 (3)	C31—C30—H30	120.1
O2—C10—C9	116.7 (3)	C29—C30—H30	120.1
O2—C10—C11	122.6 (4)	C30—C31—C32	121.9 (3)
C9—C10—C11	120.7 (4)	C30—C31—H31	119.0
C12—C11—C10	120.2 (4)	C32—C31—H31	119.0
C12—C11—H11	119.9	C31—C32—C33	121.7 (3)
C10—C11—H11	119.9	C31—C32—C37	119.6 (3)
C11—C12—C13	121.9 (4)	C33—C32—C37	118.7 (3)
C11—C12—H12	119.0	C34—C33—C32	121.6 (3)
C13—C12—H12	119.0	C34—C33—H33	119.2
C12—C13—C14	121.3 (4)	C32—C33—H33	119.2
C12—C13—C18	119.2 (4)	C33—C34—C35	119.4 (4)
C14—C13—C18	119.5 (4)	C33—C34—H34	120.3
C15—C14—C13	121.9 (4)	C35—C34—H34	120.3
C15—C14—H14	119.1	C36—C35—C34	120.7 (4)
C13—C14—H14	119.1	C36—C35—H35	119.7
C14—C15—C16	118.8 (4)	C34—C35—H35	119.7
C14—C15—H15	120.6	C35—C36—C37	121.7 (3)
C16—C15—H15	120.6	C35—C36—H36	119.2
C17—C16—C15	121.0 (4)	C37—C36—H36	119.2
C17—C16—H16	119.5	C36—C37—C32	117.9 (3)
C15—C16—H16	119.5	C36—C37—C28	123.7 (3)
C16—C17—C18	121.7 (3)	C32—C37—C28	118.4 (3)
C16—C17—H17	119.2	O4—C38—H38A	109.5
C18—C17—H17	119.2	O4—C38—H38B	109.5
C17—C18—C13	117.1 (3)	H38A—C38—H38B	109.5
C17—C18—C9	123.8 (3)	O4—C38—H38C	109.5
C13—C18—C9	119.1 (3)	H38A—C38—H38C	109.5
O2—C19—H19A	109.5	H38B—C38—H38C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.90 (1)	2.02 (1)	2.901 (3)	166 (3)
N3—H3···O1ii	0.90 (1)	2.07 (2)	2.917 (3)	156 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.90 (1)	2.02 (1)	2.901 (3)	166 (3)
N3—H3⋯O1ii	0.90 (1)	2.07 (2)	2.917 (3)	156 (3)

Symmetry codes: (i) ; (ii) .