N'-(4-Diethyl-amino-2-hy-droxy-benzyl-idene)-4-methyl-benzohydrazide.

The title compound, C(19)H(23)N(3)O(2), was prepared by condensing 4-diethyl-amino-2-hy-droxy-benzaldehyde and 4-methyl-benzo-hydrazide in methanol. The asymmetric unit contains two independent mol-ecules in which the two benzene rings make dihedral angles of 30.3 (3) and 18.9 (3)°. Intra-molecular O-H⋯N hydrogen bonds are observed in both mol-ecules. The crystal structure is stabilized by N-H⋯O hydrogen bonds, which form chains along the a axis.

Related literature

For the structures of similar hydrazone compounds, see: Fun et al. (2011 ▶); Horkaew et al. (2011 ▶); Zhi et al. (2011 ▶); Huang & Wu (2010 ▶); Shen et al. (2012 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C19H23N3O2

M = 325.40

Triclinic,

a = 9.923 (2) Å

b = 11.963 (2) Å

c = 15.827 (2) Å

α = 95.269 (2)°

β = 98.932 (2)°

γ = 103.691 (2)°

V = 1787.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.13 × 0.10 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.990, T max = 0.994

13230 measured reflections

6512 independent reflections

1651 reflections with I > 2σ(I)

R int = 0.137

Refinement

R[F 2 > 2σ(F 2)] = 0.086

wR(F 2) = 0.245

S = 0.85

6512 reflections

449 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812010690/sj5209sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010690/sj5209Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812010690/sj5209Isup3.cml

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

C19H23N3O2	Z = 4
Mr = 325.40	F(000) = 696
Triclinic, P1	Dx = 1.209 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.923 (2) Å	Cell parameters from 358 reflections
b = 11.963 (2) Å	θ = 2.3–23.7°
c = 15.827 (2) Å	µ = 0.08 mm−1
α = 95.269 (2)°	T = 298 K
β = 98.932 (2)°	Block, colorless
γ = 103.691 (2)°	0.13 × 0.10 × 0.08 mm
V = 1787.0 (5) Å3

Bruker SMART CCD area-detector diffractometer	6512 independent reflections
Radiation source: fine-focus sealed tube	1651 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.137
ω scans	θmax = 25.5°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→12
Tmin = 0.990, Tmax = 0.994	k = −14→14
13230 measured reflections	l = −19→19

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)] = 0.086	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.245	H atoms treated by a mixture of independent and constrained refinement
S = 0.85	w = 1/[σ2(Fo2) + (0.0734P)2] where P = (Fo2 + 2Fc2)/3
6512 reflections	(Δ/σ)max = 0.002
449 parameters	Δρmax = 0.35 e Å−3
7 restraints	Δρmin = −0.30 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
N1	0.9155 (5)	0.6833 (5)	0.8899 (4)	0.0555 (16)
N2	0.9803 (6)	0.7347 (5)	0.9734 (4)	0.0548 (16)
N3	0.7708 (8)	0.4048 (6)	0.5086 (4)	0.091 (3)
N4	0.4397 (6)	0.6246 (5)	0.9527 (3)	0.0497 (15)
N5	0.4905 (5)	0.7327 (5)	1.0014 (4)	0.0465 (14)
N6	0.3516 (6)	0.1601 (5)	0.6941 (4)	0.0610 (17)
O1	0.7408 (5)	0.6651 (4)	0.7424 (3)	0.0652 (14)
H1	0.7676	0.6823	0.7947	0.098*
O2	0.7941 (5)	0.8102 (4)	0.9873 (3)	0.0597 (14)
O3	0.2415 (5)	0.4445 (4)	0.8802 (3)	0.0631 (14)
O4	0.2712 (5)	0.7437 (4)	1.0126 (3)	0.0649 (15)
C1	0.9216 (7)	0.5602 (6)	0.7634 (4)	0.0473 (18)
C2	0.8067 (8)	0.5856 (6)	0.7119 (4)	0.0526 (19)
C3	0.7584 (7)	0.5351 (6)	0.6274 (5)	0.059 (2)
H3A	0.6860	0.5570	0.5937	0.071*
C4	0.8177 (8)	0.4515 (6)	0.5924 (5)	0.063 (2)
C5	0.9315 (8)	0.4241 (6)	0.6437 (4)	0.066 (2)
H5A	0.9735	0.3692	0.6213	0.080*
C6	0.9797 (7)	0.4776 (6)	0.7254 (5)	0.059 (2)
H6	1.0554	0.4584	0.7579	0.071*
C7	0.9772 (7)	0.6152 (6)	0.8517 (4)	0.0527 (19)
H7	1.0588	0.6011	0.8813	0.063*
C8	0.9117 (8)	0.8019 (6)	1.0165 (4)	0.0504 (19)
C9	0.9927 (7)	0.8600 (6)	1.1021 (4)	0.0480 (18)
C10	0.9922 (7)	0.9737 (6)	1.1256 (5)	0.056 (2)
H10	0.9404	1.0101	1.0881	0.068*
C11	1.0673 (8)	1.0348 (6)	1.2039 (5)	0.065 (2)
H11	1.0656	1.1116	1.2180	0.078*
C12	1.1440 (8)	0.9839 (8)	1.2609 (5)	0.073 (2)
C13	1.1380 (8)	0.8669 (7)	1.2397 (5)	0.069 (2)
H13	1.1831	0.8284	1.2790	0.083*
C14	1.0655 (7)	0.8080 (6)	1.1605 (5)	0.062 (2)
H14	1.0660	0.7309	1.1465	0.075*
C15	1.2289 (8)	1.0512 (6)	1.3466 (4)	0.094 (3)
H15A	1.3126	1.1038	1.3366	0.141*
H15B	1.2548	0.9979	1.3839	0.141*
H15C	1.1728	1.0943	1.3732	0.141*
C16	0.8588 (10)	0.3486 (8)	0.4632 (6)	0.151 (5)
H16A	0.8486	0.3637	0.4037	0.182*
H16B	0.9571	0.3788	0.4903	0.182*
C17	0.8153 (10)	0.2270 (8)	0.4666 (6)	0.135 (4)
H17A	0.8250	0.2130	0.5257	0.202*
H17B	0.8732	0.1884	0.4376	0.202*
H17C	0.7185	0.1977	0.4387	0.202*
C18	0.6394 (8)	0.4169 (7)	0.4535 (5)	0.078 (2)
H18A	0.5719	0.4274	0.4898	0.094*
H18B	0.5976	0.3462	0.4136	0.094*
C19	0.6687 (9)	0.5177 (7)	0.4035 (5)	0.110 (3)
H19A	0.7166	0.5870	0.4425	0.166*
H19B	0.5814	0.5272	0.3732	0.166*
H19C	0.7271	0.5035	0.3628	0.166*
C20	0.4824 (8)	0.4717 (6)	0.8644 (4)	0.0478 (18)
C21	0.3419 (8)	0.4062 (6)	0.8446 (4)	0.0521 (19)
C22	0.2982 (7)	0.3076 (6)	0.7870 (4)	0.0521 (19)
H22	0.2025	0.2706	0.7721	0.063*
C23	0.3943 (8)	0.2620 (6)	0.7503 (4)	0.056 (2)
C24	0.5391 (7)	0.3225 (6)	0.7723 (4)	0.0548 (19)
H24	0.6070	0.2936	0.7496	0.066*
C25	0.5766 (7)	0.4243 (5)	0.8276 (4)	0.0525 (19)
H25	0.6716	0.4638	0.8411	0.063*
C26	0.5295 (7)	0.5816 (6)	0.9197 (4)	0.0465 (18)
H26	0.6246	0.6210	0.9313	0.056*
C27	0.3997 (8)	0.7875 (6)	1.0303 (4)	0.0487 (18)
C28	0.4626 (7)	0.9045 (6)	1.0813 (4)	0.0440 (17)
C29	0.6076 (8)	0.9461 (6)	1.1139 (4)	0.060 (2)
H29	0.6682	0.8997	1.1042	0.072*
C30	0.6610 (8)	1.0558 (6)	1.1605 (4)	0.063 (2)
H30	0.7575	1.0828	1.1813	0.075*
C31	0.5727 (9)	1.1254 (6)	1.1764 (4)	0.057 (2)
C32	0.4292 (9)	1.0833 (6)	1.1442 (5)	0.063 (2)
H32	0.3675	1.1287	1.1541	0.076*
C33	0.3786 (7)	0.9747 (6)	1.0976 (4)	0.0529 (19)
H33	0.2822	0.9482	1.0764	0.063*
C34	0.6319 (8)	1.2448 (6)	1.2281 (4)	0.087 (3)
H34A	0.6889	1.2944	1.1957	0.130*
H34B	0.6885	1.2388	1.2816	0.130*
H34C	0.5557	1.2770	1.2397	0.130*
C35	0.2048 (8)	0.0962 (6)	0.6689 (5)	0.076 (2)
H35A	0.1586	0.1014	0.7183	0.091*
H35B	0.2002	0.0150	0.6528	0.091*
C36	0.1260 (9)	0.1388 (8)	0.5955 (5)	0.118 (3)
H36A	0.1224	0.2170	0.6127	0.177*
H36B	0.0317	0.0898	0.5796	0.177*
H36C	0.1731	0.1370	0.5470	0.177*
C37	0.4532 (8)	0.1073 (6)	0.6589 (5)	0.080 (2)
H37A	0.4124	0.0243	0.6448	0.096*
H37B	0.5367	0.1193	0.7030	0.096*
C38	0.4959 (9)	0.1541 (8)	0.5807 (5)	0.122 (4)
H38A	0.4136	0.1455	0.5373	0.183*
H38B	0.5576	0.1122	0.5590	0.183*
H38C	0.5443	0.2348	0.5952	0.183*
H2	1.068 (3)	0.726 (5)	0.988 (4)	0.080*
H5	0.580 (2)	0.773 (5)	1.003 (4)	0.080*
H3	0.2612 (18)	0.512 (2)	0.909 (4)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.044 (4)	0.066 (4)	0.054 (4)	0.018 (3)	0.005 (3)	−0.003 (3)
N2	0.036 (4)	0.067 (4)	0.056 (4)	0.016 (3)	−0.002 (3)	−0.012 (3)
N3	0.092 (6)	0.135 (7)	0.063 (5)	0.074 (5)	0.010 (5)	−0.019 (5)
N4	0.054 (4)	0.041 (4)	0.050 (4)	0.011 (3)	−0.002 (3)	0.007 (3)
N5	0.040 (4)	0.052 (4)	0.049 (4)	0.009 (3)	0.012 (3)	0.012 (3)
N6	0.053 (4)	0.066 (4)	0.063 (4)	0.013 (4)	0.019 (4)	−0.003 (3)
O1	0.065 (4)	0.071 (3)	0.061 (3)	0.032 (3)	0.005 (3)	−0.010 (3)
O2	0.036 (3)	0.076 (3)	0.064 (3)	0.016 (3)	0.005 (3)	−0.006 (3)
O3	0.051 (3)	0.061 (3)	0.072 (4)	0.011 (3)	0.010 (3)	−0.007 (3)
O4	0.035 (3)	0.077 (4)	0.077 (4)	0.013 (3)	0.005 (3)	−0.009 (3)
C1	0.045 (5)	0.060 (5)	0.038 (4)	0.016 (4)	0.008 (4)	−0.003 (4)
C2	0.058 (5)	0.053 (5)	0.046 (5)	0.008 (4)	0.017 (4)	0.003 (4)
C3	0.054 (5)	0.066 (5)	0.058 (5)	0.022 (4)	0.003 (4)	0.012 (4)
C4	0.070 (6)	0.070 (6)	0.040 (5)	0.015 (5)	0.001 (4)	−0.008 (4)
C5	0.070 (6)	0.091 (6)	0.041 (5)	0.032 (5)	0.003 (4)	−0.003 (4)
C6	0.044 (5)	0.080 (5)	0.059 (5)	0.031 (4)	0.005 (4)	0.008 (4)
C7	0.040 (5)	0.068 (5)	0.054 (5)	0.018 (4)	0.011 (4)	0.008 (4)
C8	0.051 (5)	0.046 (5)	0.053 (5)	0.008 (4)	0.009 (4)	0.011 (4)
C9	0.028 (4)	0.069 (5)	0.042 (4)	0.005 (4)	0.008 (4)	−0.004 (4)
C10	0.049 (5)	0.059 (5)	0.065 (5)	0.019 (4)	0.017 (4)	0.004 (4)
C11	0.067 (6)	0.054 (5)	0.063 (5)	−0.001 (4)	0.021 (5)	−0.016 (5)
C12	0.055 (6)	0.095 (7)	0.051 (5)	0.000 (5)	0.002 (4)	−0.009 (5)
C13	0.061 (6)	0.086 (6)	0.059 (6)	0.019 (5)	0.005 (5)	0.008 (5)
C14	0.048 (5)	0.076 (6)	0.063 (5)	0.018 (4)	0.012 (4)	0.003 (5)
C15	0.091 (7)	0.114 (7)	0.056 (5)	0.005 (6)	0.001 (5)	−0.012 (5)
C16	0.188 (13)	0.106 (9)	0.091 (8)	−0.036 (9)	−0.081 (8)	0.031 (7)
C17	0.149 (10)	0.135 (9)	0.109 (8)	0.034 (8)	−0.008 (7)	0.016 (7)
C18	0.069 (6)	0.100 (7)	0.063 (5)	0.033 (5)	0.000 (5)	−0.007 (5)
C19	0.111 (8)	0.144 (9)	0.095 (7)	0.048 (7)	0.035 (6)	0.045 (7)
C20	0.046 (5)	0.047 (5)	0.050 (5)	0.008 (4)	0.015 (4)	0.006 (4)
C21	0.060 (6)	0.067 (5)	0.046 (5)	0.034 (5)	0.024 (4)	0.019 (4)
C22	0.046 (5)	0.049 (5)	0.054 (5)	0.006 (4)	0.003 (4)	−0.003 (4)
C23	0.062 (6)	0.053 (5)	0.052 (5)	0.015 (5)	0.013 (4)	0.001 (4)
C24	0.046 (5)	0.054 (5)	0.065 (5)	0.013 (4)	0.019 (4)	−0.002 (4)
C25	0.058 (5)	0.050 (5)	0.043 (4)	0.004 (4)	0.006 (4)	0.005 (4)
C26	0.042 (5)	0.060 (5)	0.041 (4)	0.014 (4)	0.008 (4)	0.016 (4)
C27	0.057 (5)	0.058 (5)	0.037 (4)	0.020 (5)	0.012 (4)	0.013 (4)
C28	0.035 (5)	0.050 (5)	0.042 (4)	0.007 (4)	−0.001 (4)	0.007 (4)
C29	0.054 (6)	0.067 (5)	0.060 (5)	0.028 (4)	0.003 (4)	−0.008 (4)
C30	0.054 (5)	0.078 (6)	0.050 (5)	0.014 (5)	0.004 (4)	−0.002 (4)
C31	0.083 (6)	0.049 (5)	0.037 (4)	0.021 (5)	0.012 (5)	−0.005 (4)
C32	0.063 (6)	0.058 (5)	0.076 (6)	0.028 (5)	0.022 (5)	0.001 (4)
C33	0.029 (4)	0.061 (5)	0.063 (5)	0.003 (4)	0.004 (4)	0.012 (4)
C34	0.110 (7)	0.073 (6)	0.064 (5)	0.018 (5)	−0.007 (5)	−0.009 (5)
C35	0.059 (6)	0.069 (6)	0.080 (6)	−0.013 (5)	0.009 (5)	−0.009 (5)
C36	0.086 (7)	0.169 (10)	0.078 (6)	0.013 (7)	−0.016 (6)	0.015 (7)
C37	0.076 (6)	0.062 (5)	0.088 (6)	0.005 (5)	0.005 (5)	−0.016 (5)
C38	0.115 (8)	0.192 (10)	0.067 (6)	0.045 (7)	0.038 (6)	0.007 (7)

N1—C7	1.290 (7)	C16—H16B	0.9700
N1—N2	1.392 (7)	C17—H17A	0.9600
N2—C8	1.371 (8)	C17—H17B	0.9600
N2—H2	0.898 (11)	C17—H17C	0.9600
N3—C4	1.355 (8)	C18—C19	1.498 (9)
N3—C16	1.455 (8)	C18—H18A	0.9700
N3—C18	1.497 (8)	C18—H18B	0.9700
N4—C26	1.282 (7)	C19—H19A	0.9600
N4—N5	1.382 (7)	C19—H19B	0.9600
N5—C27	1.342 (8)	C19—H19C	0.9600
N5—H5	0.901 (11)	C20—C25	1.375 (8)
N6—C23	1.378 (7)	C20—C21	1.400 (8)
N6—C35	1.449 (8)	C20—C26	1.444 (8)
N6—C37	1.461 (8)	C21—C22	1.359 (8)
O1—C2	1.369 (7)	C22—C23	1.380 (8)
O1—H1	0.8200	C22—H22	0.9300
O2—C8	1.217 (7)	C23—C24	1.420 (8)
O3—C21	1.365 (7)	C24—C25	1.371 (8)
O3—H3	0.847 (10)	C24—H24	0.9300
O4—C27	1.235 (7)	C25—H25	0.9300
C1—C6	1.392 (8)	C26—H26	0.9300
C1—C2	1.406 (8)	C27—C28	1.492 (8)
C1—C7	1.453 (8)	C28—C33	1.351 (8)
C2—C3	1.379 (8)	C28—C29	1.402 (8)
C3—C4	1.389 (8)	C29—C30	1.385 (8)
C3—H3A	0.9300	C29—H29	0.9300
C4—C5	1.407 (8)	C30—C31	1.379 (8)
C5—C6	1.350 (8)	C30—H30	0.9300
C5—H5A	0.9300	C31—C32	1.389 (9)
C6—H6	0.9300	C31—C34	1.515 (8)
C7—H7	0.9300	C32—C33	1.372 (8)
C8—C9	1.479 (8)	C32—H32	0.9300
C9—C14	1.369 (8)	C33—H33	0.9300
C9—C10	1.378 (8)	C34—H34A	0.9600
C10—C11	1.385 (8)	C34—H34B	0.9600
C10—H10	0.9300	C34—H34C	0.9600
C11—C12	1.368 (9)	C35—C36	1.497 (9)
C11—H11	0.9300	C35—H35A	0.9700
C12—C13	1.394 (9)	C35—H35B	0.9700
C12—C15	1.523 (9)	C36—H36A	0.9600
C13—C14	1.379 (8)	C36—H36B	0.9600
C13—H13	0.9300	C36—H36C	0.9600
C14—H14	0.9300	C37—C38	1.485 (9)
C15—H15A	0.9600	C37—H37A	0.9700
C15—H15B	0.9600	C37—H37B	0.9700
C15—H15C	0.9600	C38—H38A	0.9600
C16—C17	1.424 (7)	C38—H38B	0.9600
C16—H16A	0.9700	C38—H38C	0.9600
C7—N1—N2	116.5 (5)	C19—C18—H18B	109.3
C8—N2—N1	117.1 (5)	H18A—C18—H18B	107.9
C8—N2—H2	129 (4)	C18—C19—H19A	109.5
N1—N2—H2	113 (4)	C18—C19—H19B	109.5
C4—N3—C16	119.6 (7)	H19A—C19—H19B	109.5
C4—N3—C18	125.1 (6)	C18—C19—H19C	109.5
C16—N3—C18	114.9 (7)	H19A—C19—H19C	109.5
C26—N4—N5	116.8 (6)	H19B—C19—H19C	109.5
C27—N5—N4	119.6 (6)	C25—C20—C21	115.6 (7)
C27—N5—H5	119 (4)	C25—C20—C26	120.7 (7)
N4—N5—H5	120 (4)	C21—C20—C26	123.7 (7)
C23—N6—C35	122.5 (6)	C22—C21—O3	117.5 (7)
C23—N6—C37	121.6 (6)	C22—C21—C20	122.6 (7)
C35—N6—C37	115.9 (6)	O3—C21—C20	119.7 (7)
C2—O1—H1	109.5	C21—C22—C23	120.7 (7)
C21—O3—H3	120.6 (17)	C21—C22—H22	119.7
C6—C1—C2	116.3 (6)	C23—C22—H22	119.7
C6—C1—C7	121.0 (7)	N6—C23—C22	121.1 (7)
C2—C1—C7	122.7 (6)	N6—C23—C24	120.5 (7)
O1—C2—C3	116.7 (7)	C22—C23—C24	118.4 (7)
O1—C2—C1	121.5 (6)	C25—C24—C23	118.5 (7)
C3—C2—C1	121.7 (7)	C25—C24—H24	120.7
C2—C3—C4	120.1 (7)	C23—C24—H24	120.7
C2—C3—H3A	120.0	C24—C25—C20	124.0 (7)
C4—C3—H3A	120.0	C24—C25—H25	118.0
N3—C4—C3	119.2 (7)	C20—C25—H25	118.0
N3—C4—C5	122.1 (7)	N4—C26—C20	119.7 (7)
C3—C4—C5	118.6 (7)	N4—C26—H26	120.2
C6—C5—C4	120.0 (7)	C20—C26—H26	120.2
C6—C5—H5A	120.0	O4—C27—N5	121.0 (7)
C4—C5—H5A	120.0	O4—C27—C28	122.6 (7)
C5—C6—C1	123.1 (7)	N5—C27—C28	116.3 (7)
C5—C6—H6	118.4	C33—C28—C29	117.6 (6)
C1—C6—H6	118.4	C33—C28—C27	119.8 (7)
N1—C7—C1	121.2 (6)	C29—C28—C27	122.6 (7)
N1—C7—H7	119.4	C30—C29—C28	120.5 (7)
C1—C7—H7	119.4	C30—C29—H29	119.8
O2—C8—N2	122.7 (7)	C28—C29—H29	119.8
O2—C8—C9	123.8 (7)	C31—C30—C29	120.6 (7)
N2—C8—C9	113.5 (6)	C31—C30—H30	119.7
C14—C9—C10	117.6 (7)	C29—C30—H30	119.7
C14—C9—C8	124.7 (7)	C30—C31—C32	118.5 (7)
C10—C9—C8	117.7 (7)	C30—C31—C34	120.3 (8)
C9—C10—C11	121.3 (7)	C32—C31—C34	121.2 (7)
C9—C10—H10	119.3	C33—C32—C31	119.9 (7)
C11—C10—H10	119.3	C33—C32—H32	120.1
C12—C11—C10	121.0 (7)	C31—C32—H32	120.1
C12—C11—H11	119.5	C28—C33—C32	122.9 (7)
C10—C11—H11	119.5	C28—C33—H33	118.6
C11—C12—C13	117.9 (7)	C32—C33—H33	118.6
C11—C12—C15	121.3 (8)	C31—C34—H34A	109.5
C13—C12—C15	120.8 (8)	C31—C34—H34B	109.5
C14—C13—C12	120.3 (7)	H34A—C34—H34B	109.5
C14—C13—H13	119.8	C31—C34—H34C	109.5
C12—C13—H13	119.8	H34A—C34—H34C	109.5
C9—C14—C13	121.7 (7)	H34B—C34—H34C	109.5
C9—C14—H14	119.1	N6—C35—C36	113.7 (6)
C13—C14—H14	119.1	N6—C35—H35A	108.8
C12—C15—H15A	109.5	C36—C35—H35A	108.8
C12—C15—H15B	109.5	N6—C35—H35B	108.8
H15A—C15—H15B	109.5	C36—C35—H35B	108.8
C12—C15—H15C	109.5	H35A—C35—H35B	107.7
H15A—C15—H15C	109.5	C35—C36—H36A	109.5
H15B—C15—H15C	109.5	C35—C36—H36B	109.5
C17—C16—N3	108.2 (8)	H36A—C36—H36B	109.5
C17—C16—H16A	110.1	C35—C36—H36C	109.5
N3—C16—H16A	110.1	H36A—C36—H36C	109.5
C17—C16—H16B	110.1	H36B—C36—H36C	109.5
N3—C16—H16B	110.1	N6—C37—C38	113.9 (7)
H16A—C16—H16B	108.4	N6—C37—H37A	108.8
C16—C17—H17A	109.5	C38—C37—H37A	108.8
C16—C17—H17B	109.5	N6—C37—H37B	108.8
H17A—C17—H17B	109.5	C38—C37—H37B	108.8
C16—C17—H17C	109.5	H37A—C37—H37B	107.7
H17A—C17—H17C	109.5	C37—C38—H38A	109.5
H17B—C17—H17C	109.5	C37—C38—H38B	109.5
N3—C18—C19	111.8 (7)	H38A—C38—H38B	109.5
N3—C18—H18A	109.3	C37—C38—H38C	109.5
C19—C18—H18A	109.3	H38A—C38—H38C	109.5
N3—C18—H18B	109.3	H38B—C38—H38C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4i	0.90 (1)	1.95 (2)	2.831 (7)	167 (6)
O1—H1···N1	0.82	1.93	2.641 (7)	145
N5—H5···O2	0.90 (1)	2.12 (2)	2.985 (7)	160 (6)
O3—H3···N4	0.85 (1)	1.94 (1)	2.581 (7)	132 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4i	0.90 (1)	1.95 (2)	2.831 (7)	167 (6)
O1—H1⋯N1	0.82	1.93	2.641 (7)	145
N5—H5⋯O2	0.90 (1)	2.12 (2)	2.985 (7)	160 (6)
O3—H3⋯N4	0.85 (1)	1.94 (1)	2.581 (7)	132 (2)

Symmetry code: (i) .