N'-(3-Eth-oxy-2-hy-droxy-benzyl-idene)-2-hy-droxy-3-methyl-benzohydrazide.

The title compound, C(17)H(18)N(2)O(4), crystallizes with two independent mol-ecules in the asymmetric unit. The two benzene rings in each mol-ecule make dihedral angles of 7.6 (3) and 3.9 (3)°. Intra-molecular O-H⋯N and O-H⋯O hydrogen bonds are present in each mol-ecule. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into chains propagating in [010]. The are also a number of C-H⋯O and π-π inter-actions present [centroid-centroid distances = 3.874 (4) and 3.904 (3) Å], that result in the formation of a three-dimensional network.

Related literature

For the crystal 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 ▶).

Experimental

Crystal data

C17H18N2O4

M = 314.33

Monoclinic,

a = 7.7661 (17) Å

b = 22.148 (3) Å

c = 9.7002 (16) Å

β = 100.382 (2)°

V = 1641.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.982, T max = 0.984

8061 measured reflections

3436 independent reflections

1592 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.113

S = 0.97

3436 reflections

431 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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/S1600536812002127/su2365sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002127/su2365Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812002127/su2365Isup3.cml

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

C17H18N2O4	F(000) = 664
Mr = 314.33	Dx = 1.272 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 756 reflections
a = 7.7661 (17) Å	θ = 2.3–24.1°
b = 22.148 (3) Å	µ = 0.09 mm−1
c = 9.7002 (16) Å	T = 298 K
β = 100.382 (2)°	Block, colourless
V = 1641.1 (5) Å3	0.20 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3436 independent reflections
Radiation source: fine-focus sealed tube	1592 reflections with I > 2σ(I)
graphite	Rint = 0.058
ω scans	θmax = 26.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −7→9
Tmin = 0.982, Tmax = 0.984	k = −26→27
8061 measured reflections	l = −11→12

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ2(Fo2) + (0.033P)2] where P = (Fo2 + 2Fc2)/3
3436 reflections	(Δ/σ)max < 0.001
431 parameters	Δρmax = 0.13 e Å−3
4 restraints	Δρmin = −0.15 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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	0.1824 (5)	0.21340 (14)	0.6459 (3)	0.0614 (14)
O2	0.2554 (5)	0.17087 (16)	0.9028 (4)	0.0698 (16)
O3	0.0043 (6)	0.24281 (18)	0.2650 (4)	0.0890 (19)
O4	−0.1208 (6)	0.23100 (17)	0.0048 (4)	0.0893 (17)
N1	0.1655 (6)	0.3042 (2)	0.4810 (5)	0.0631 (17)
N2	0.1167 (6)	0.3313 (2)	0.3504 (5)	0.0658 (19)
C1	0.2983 (7)	0.3115 (3)	0.7185 (6)	0.063 (2)
C2	0.2635 (6)	0.2517 (2)	0.7481 (5)	0.057 (2)
C3	0.3042 (7)	0.2287 (3)	0.8847 (6)	0.065 (2)
C4	0.3899 (9)	0.2654 (4)	0.9877 (7)	0.104 (3)
C5	0.4308 (10)	0.3244 (4)	0.9603 (8)	0.126 (4)
C6	0.3823 (9)	0.3481 (3)	0.8288 (8)	0.099 (3)
C7	0.2473 (7)	0.3374 (3)	0.5801 (6)	0.068 (3)
C8	0.0341 (8)	0.2960 (3)	0.2444 (6)	0.064 (2)
C9	−0.0216 (7)	0.3263 (2)	0.1074 (6)	0.057 (2)
C10	−0.0924 (7)	0.2907 (3)	−0.0083 (6)	0.069 (2)
C11	−0.1371 (8)	0.3159 (3)	−0.1414 (7)	0.080 (3)
C12	−0.1147 (9)	0.3763 (4)	−0.1557 (7)	0.097 (3)
C13	−0.0494 (9)	0.4132 (3)	−0.0452 (7)	0.094 (3)
C14	−0.0006 (8)	0.3884 (3)	0.0874 (6)	0.081 (3)
C15	−0.2122 (9)	0.2749 (3)	−0.2636 (7)	0.115 (3)
C16	0.2750 (8)	0.1487 (3)	1.0453 (6)	0.081 (3)
C17	0.1917 (9)	0.0870 (3)	1.0394 (6)	0.101 (3)
O5	−0.1527 (4)	−0.03370 (15)	0.5987 (4)	0.0601 (16)
O6	0.2365 (5)	0.00000 (16)	0.4276 (4)	0.0735 (17)
O7	−0.4309 (5)	−0.07716 (17)	0.6760 (4)	0.0754 (17)
O8	0.5012 (5)	−0.01235 (19)	0.3106 (4)	0.0801 (17)
N3	0.0562 (6)	0.05665 (19)	0.5918 (4)	0.0544 (17)
N4	0.1951 (6)	0.0840 (2)	0.5477 (5)	0.0597 (17)
C18	−0.1801 (7)	0.0613 (2)	0.7159 (5)	0.053 (2)
C19	−0.2382 (7)	0.0038 (2)	0.6776 (5)	0.0515 (19)
C20	−0.3885 (7)	−0.0194 (3)	0.7188 (6)	0.061 (2)
C21	−0.4786 (8)	0.0161 (3)	0.7980 (6)	0.082 (3)
C22	−0.4209 (9)	0.0736 (3)	0.8346 (7)	0.089 (3)
C23	−0.2746 (8)	0.0965 (3)	0.7968 (6)	0.075 (3)
C24	−0.0276 (7)	0.0874 (2)	0.6696 (6)	0.060 (2)
C25	0.2855 (7)	0.0518 (3)	0.4634 (6)	0.060 (2)
C26	0.4379 (7)	0.0804 (2)	0.4208 (5)	0.055 (2)
C27	0.5402 (8)	0.0456 (3)	0.3454 (6)	0.061 (2)
C28	0.6896 (8)	0.0694 (3)	0.3020 (6)	0.071 (3)
C29	0.7313 (8)	0.1279 (3)	0.3357 (7)	0.082 (3)
C30	0.6338 (9)	0.1639 (3)	0.4091 (7)	0.087 (3)
C31	0.4889 (8)	0.1399 (3)	0.4511 (6)	0.077 (3)
C32	0.7986 (9)	0.0305 (4)	0.2240 (7)	0.106 (3)
C33	−0.6007 (7)	−0.0994 (3)	0.6885 (6)	0.080 (3)
C34	−0.6145 (10)	−0.1627 (3)	0.6347 (8)	0.124 (4)
H1	0.16610	0.23080	0.57010	0.0920*
H2	0.147 (6)	0.3700 (9)	0.338 (5)	0.0800*
H4A	0.42150	0.25040	1.07830	0.1240*
H4B	−0.10510	0.22200	0.08810	0.1340*
H5A	0.49160	0.34820	1.03180	0.1520*
H6	0.40510	0.38840	0.81230	0.1180*
H7	0.27330	0.37740	0.56320	0.0810*
H12	−0.14490	0.39330	−0.24440	0.1170*
H13	−0.03800	0.45450	−0.05900	0.1120*
H14	0.04590	0.41280	0.16290	0.0980*
H15A	−0.24110	0.29850	−0.34760	0.1720*
H15B	−0.31570	0.25540	−0.24440	0.1720*
H15C	−0.12690	0.24490	−0.27580	0.1720*
H16A	0.21790	0.17580	1.10140	0.0970*
H16B	0.39800	0.14610	1.08710	0.0970*
H17A	0.06800	0.09060	1.00610	0.1510*
H17B	0.21200	0.06940	1.13140	0.1510*
H17C	0.24200	0.06160	0.97680	0.1510*
H4	0.243 (7)	0.1196 (13)	0.577 (5)	0.0800*
H5	−0.07000	−0.01560	0.57610	0.0900*
H8	0.397 (3)	−0.015 (3)	0.327 (6)	0.0800*
H21	−0.57850	0.00130	0.82670	0.0980*
H22	−0.48410	0.09740	0.88680	0.1080*
H23	−0.23710	0.13530	0.82430	0.0910*
H24	0.00870	0.12640	0.69670	0.0720*
H29	0.82990	0.14440	0.30810	0.0990*
H30	0.66600	0.20380	0.42960	0.1050*
H31	0.42330	0.16390	0.50080	0.0920*
H32A	0.73200	0.02030	0.13370	0.1580*
H32B	0.83150	−0.00580	0.27630	0.1580*
H32C	0.90200	0.05220	0.21210	0.1580*
H33A	−0.69100	−0.07450	0.63430	0.0950*
H33B	−0.61510	−0.09850	0.78580	0.0950*
H34A	−0.60150	−0.16290	0.53820	0.1870*
H34B	−0.72690	−0.17890	0.64270	0.1870*
H34C	−0.52410	−0.18680	0.68870	0.1870*

	U11	U22	U33	U12	U13	U23
O1	0.084 (3)	0.041 (2)	0.058 (2)	−0.008 (2)	0.010 (2)	−0.0046 (18)
O2	0.089 (3)	0.061 (3)	0.060 (2)	−0.002 (2)	0.0147 (19)	0.006 (2)
O3	0.132 (4)	0.049 (3)	0.084 (3)	−0.022 (3)	0.014 (2)	0.005 (2)
O4	0.105 (3)	0.057 (3)	0.100 (3)	−0.002 (3)	0.003 (3)	−0.009 (2)
N1	0.076 (3)	0.040 (3)	0.073 (3)	−0.006 (3)	0.013 (3)	0.000 (3)
N2	0.084 (4)	0.037 (3)	0.075 (3)	−0.006 (3)	0.011 (3)	0.009 (3)
C1	0.067 (4)	0.048 (4)	0.072 (4)	0.001 (3)	0.011 (3)	−0.002 (3)
C2	0.059 (4)	0.054 (4)	0.056 (4)	−0.003 (3)	0.007 (3)	−0.003 (3)
C3	0.073 (4)	0.058 (4)	0.062 (4)	−0.001 (3)	0.010 (3)	−0.002 (3)
C4	0.141 (7)	0.085 (6)	0.075 (5)	−0.024 (5)	−0.006 (4)	−0.002 (4)
C5	0.172 (8)	0.113 (7)	0.074 (5)	−0.030 (6)	−0.030 (5)	−0.025 (5)
C6	0.126 (6)	0.058 (4)	0.104 (5)	−0.023 (4)	−0.002 (5)	−0.022 (4)
C7	0.075 (4)	0.043 (4)	0.086 (5)	−0.001 (3)	0.016 (3)	0.003 (3)
C8	0.070 (4)	0.047 (4)	0.077 (4)	−0.001 (3)	0.018 (3)	−0.002 (3)
C9	0.067 (4)	0.039 (3)	0.065 (4)	−0.001 (3)	0.010 (3)	0.009 (3)
C10	0.071 (4)	0.057 (4)	0.078 (4)	0.007 (3)	0.014 (3)	−0.001 (4)
C11	0.093 (5)	0.078 (5)	0.066 (4)	0.019 (4)	0.005 (4)	−0.003 (4)
C12	0.126 (6)	0.094 (6)	0.075 (5)	0.024 (5)	0.027 (4)	0.016 (4)
C13	0.145 (7)	0.053 (4)	0.082 (5)	0.003 (4)	0.019 (5)	0.007 (4)
C14	0.108 (5)	0.060 (4)	0.074 (4)	−0.012 (4)	0.012 (4)	0.012 (3)
C15	0.129 (6)	0.119 (6)	0.086 (5)	0.026 (5)	−0.007 (4)	−0.018 (5)
C16	0.081 (4)	0.102 (5)	0.060 (4)	0.024 (4)	0.011 (3)	0.017 (4)
C17	0.106 (6)	0.106 (6)	0.092 (5)	−0.007 (5)	0.021 (4)	0.049 (5)
O5	0.064 (3)	0.041 (2)	0.079 (3)	−0.0014 (18)	0.023 (2)	−0.010 (2)
O6	0.072 (3)	0.045 (3)	0.108 (3)	−0.011 (2)	0.028 (2)	−0.013 (2)
O7	0.066 (3)	0.062 (3)	0.101 (3)	−0.011 (2)	0.023 (2)	−0.005 (2)
O8	0.078 (3)	0.064 (3)	0.104 (3)	0.001 (3)	0.032 (3)	−0.012 (2)
N3	0.047 (3)	0.048 (3)	0.066 (3)	−0.007 (2)	0.004 (2)	0.000 (2)
N4	0.060 (3)	0.040 (3)	0.081 (3)	−0.006 (3)	0.018 (3)	0.003 (3)
C18	0.053 (4)	0.042 (3)	0.066 (4)	0.005 (3)	0.014 (3)	0.003 (3)
C19	0.056 (4)	0.045 (3)	0.056 (3)	0.012 (3)	0.017 (3)	0.001 (3)
C20	0.059 (4)	0.055 (4)	0.070 (4)	−0.001 (3)	0.013 (3)	0.005 (3)
C21	0.077 (5)	0.078 (5)	0.100 (5)	0.009 (4)	0.041 (4)	0.006 (4)
C22	0.091 (5)	0.074 (5)	0.116 (6)	0.008 (4)	0.053 (4)	−0.011 (4)
C23	0.091 (5)	0.053 (4)	0.085 (4)	−0.002 (4)	0.025 (4)	−0.019 (3)
C24	0.065 (4)	0.038 (3)	0.074 (4)	0.005 (3)	0.004 (3)	−0.002 (3)
C25	0.055 (4)	0.057 (4)	0.065 (4)	0.003 (3)	0.007 (3)	0.008 (3)
C26	0.060 (4)	0.045 (4)	0.059 (3)	0.000 (3)	0.009 (3)	0.006 (3)
C27	0.060 (4)	0.061 (4)	0.058 (4)	−0.004 (3)	0.001 (3)	0.007 (3)
C28	0.078 (5)	0.074 (5)	0.060 (4)	0.004 (4)	0.012 (3)	0.020 (3)
C29	0.064 (5)	0.091 (6)	0.095 (5)	−0.008 (4)	0.023 (4)	0.023 (4)
C30	0.085 (5)	0.061 (4)	0.117 (5)	−0.018 (4)	0.021 (4)	0.007 (4)
C31	0.073 (4)	0.051 (4)	0.108 (5)	−0.009 (4)	0.019 (4)	0.005 (3)
C32	0.083 (5)	0.136 (7)	0.106 (5)	0.007 (5)	0.040 (4)	0.002 (5)
C33	0.065 (4)	0.086 (5)	0.090 (4)	−0.008 (4)	0.021 (3)	0.024 (4)
C34	0.123 (7)	0.105 (7)	0.154 (7)	−0.064 (5)	0.049 (5)	−0.040 (5)

O1—C2	1.369 (6)	C12—H12	0.9300
O2—C3	1.356 (7)	C13—H13	0.9300
O2—C16	1.449 (7)	C14—H14	0.9300
O3—C8	1.224 (8)	C15—H15C	0.9600
O4—C10	1.350 (8)	C15—H15A	0.9600
O1—H1	0.8200	C15—H15B	0.9600
O4—H4B	0.8200	C16—H16A	0.9700
O5—C19	1.378 (6)	C16—H16B	0.9700
O6—C25	1.239 (7)	C17—H17B	0.9600
O7—C20	1.367 (8)	C17—H17A	0.9600
O7—C33	1.433 (7)	C17—H17C	0.9600
O8—C27	1.348 (8)	C18—C19	1.380 (6)
O5—H5	0.8200	C18—C24	1.460 (8)
O8—H8	0.85 (3)	C18—C23	1.404 (8)
N1—N2	1.391 (7)	C19—C20	1.398 (8)
N1—C7	1.284 (8)	C20—C21	1.375 (9)
N2—C8	1.357 (8)	C21—C22	1.375 (9)
N2—H2	0.90 (2)	C22—C23	1.354 (9)
N3—N4	1.371 (7)	C25—C26	1.466 (8)
N3—C24	1.278 (7)	C26—C27	1.403 (8)
N4—C25	1.370 (8)	C26—C31	1.392 (8)
N4—H4	0.90 (4)	C27—C28	1.406 (9)
C1—C2	1.392 (8)	C28—C32	1.504 (10)
C1—C6	1.406 (9)	C28—C29	1.361 (9)
C1—C7	1.448 (8)	C29—C30	1.382 (9)
C2—C3	1.402 (8)	C30—C31	1.371 (9)
C3—C4	1.365 (10)	C33—C34	1.493 (9)
C4—C5	1.382 (12)	C21—H21	0.9300
C5—C6	1.368 (11)	C22—H22	0.9300
C8—C9	1.482 (8)	C23—H23	0.9300
C9—C14	1.403 (8)	C24—H24	0.9300
C9—C10	1.400 (8)	C29—H29	0.9300
C10—C11	1.392 (9)	C30—H30	0.9300
C11—C12	1.359 (11)	C31—H31	0.9300
C11—C15	1.523 (9)	C32—H32A	0.9600
C12—C13	1.370 (10)	C32—H32B	0.9600
C13—C14	1.387 (9)	C32—H32C	0.9600
C16—C17	1.509 (9)	C33—H33A	0.9700
C4—H4A	0.9300	C33—H33B	0.9700
C5—H5A	0.9300	C34—H34A	0.9600
C6—H6	0.9300	C34—H34B	0.9600
C7—H7	0.9300	C34—H34C	0.9600
C3—O2—C16	117.4 (4)	H16A—C16—H16B	109.00
C2—O1—H1	110.00	H17B—C17—H17C	109.00
C10—O4—H4B	109.00	H17A—C17—H17C	109.00
C20—O7—C33	118.1 (4)	C16—C17—H17B	110.00
C19—O5—H5	109.00	C16—C17—H17A	109.00
C27—O8—H8	101 (4)	H17A—C17—H17B	109.00
N2—N1—C7	116.8 (5)	C16—C17—H17C	110.00
N1—N2—C8	117.1 (5)	C19—C18—C24	121.8 (5)
N1—N2—H2	120 (3)	C23—C18—C24	119.2 (5)
C8—N2—H2	123 (3)	C19—C18—C23	119.0 (5)
N4—N3—C24	117.5 (4)	O5—C19—C20	116.6 (4)
N3—N4—C25	118.2 (4)	C18—C19—C20	120.8 (5)
N3—N4—H4	127 (3)	O5—C19—C18	122.6 (5)
C25—N4—H4	115 (3)	O7—C20—C19	115.2 (5)
C6—C1—C7	119.3 (6)	O7—C20—C21	125.9 (5)
C2—C1—C6	118.2 (5)	C19—C20—C21	119.0 (6)
C2—C1—C7	122.5 (5)	C20—C21—C22	119.9 (6)
O1—C2—C1	121.4 (4)	C21—C22—C23	121.8 (6)
O1—C2—C3	117.1 (4)	C18—C23—C22	119.5 (6)
C1—C2—C3	121.5 (5)	N3—C24—C18	119.9 (4)
O2—C3—C2	116.4 (5)	O6—C25—N4	119.0 (5)
C2—C3—C4	118.2 (6)	O6—C25—C26	123.0 (5)
O2—C3—C4	125.4 (6)	N4—C25—C26	118.0 (5)
C3—C4—C5	121.4 (7)	C27—C26—C31	117.6 (5)
C4—C5—C6	120.5 (7)	C25—C26—C27	118.1 (5)
C1—C6—C5	120.0 (7)	C25—C26—C31	124.3 (5)
N1—C7—C1	118.9 (6)	O8—C27—C28	116.3 (5)
N2—C8—C9	116.1 (5)	C26—C27—C28	121.7 (6)
O3—C8—N2	120.5 (5)	O8—C27—C26	122.1 (5)
O3—C8—C9	123.3 (5)	C27—C28—C29	117.3 (6)
C8—C9—C10	118.2 (5)	C27—C28—C32	120.4 (6)
C8—C9—C14	123.1 (5)	C29—C28—C32	122.4 (6)
C10—C9—C14	118.7 (5)	C28—C29—C30	123.0 (6)
C9—C10—C11	120.9 (6)	C29—C30—C31	119.0 (6)
O4—C10—C9	121.5 (5)	C26—C31—C30	121.5 (6)
O4—C10—C11	117.5 (5)	O7—C33—C34	107.6 (5)
C12—C11—C15	123.1 (6)	C20—C21—H21	120.00
C10—C11—C15	118.6 (6)	C22—C21—H21	120.00
C10—C11—C12	118.3 (6)	C21—C22—H22	119.00
C11—C12—C13	122.9 (7)	C23—C22—H22	119.00
C12—C13—C14	119.3 (6)	C18—C23—H23	120.00
C9—C14—C13	119.8 (6)	C22—C23—H23	120.00
O2—C16—C17	107.5 (5)	N3—C24—H24	120.00
C3—C4—H4A	119.00	C18—C24—H24	120.00
C5—C4—H4A	119.00	C28—C29—H29	119.00
C4—C5—H5A	120.00	C30—C29—H29	119.00
C6—C5—H5A	120.00	C29—C30—H30	120.00
C1—C6—H6	120.00	C31—C30—H30	121.00
C5—C6—H6	120.00	C26—C31—H31	119.00
N1—C7—H7	121.00	C30—C31—H31	119.00
C1—C7—H7	121.00	C28—C32—H32A	110.00
C11—C12—H12	119.00	C28—C32—H32B	110.00
C13—C12—H12	119.00	C28—C32—H32C	109.00
C14—C13—H13	120.00	H32A—C32—H32B	109.00
C12—C13—H13	120.00	H32A—C32—H32C	109.00
C13—C14—H14	120.00	H32B—C32—H32C	109.00
C9—C14—H14	120.00	O7—C33—H33A	110.00
C11—C15—H15B	110.00	O7—C33—H33B	110.00
H15A—C15—H15B	110.00	C34—C33—H33A	110.00
C11—C15—H15A	110.00	C34—C33—H33B	110.00
H15B—C15—H15C	109.00	H33A—C33—H33B	108.00
H15A—C15—H15C	109.00	C33—C34—H34A	109.00
C11—C15—H15C	109.00	C33—C34—H34B	109.00
C17—C16—H16B	110.00	C33—C34—H34C	109.00
C17—C16—H16A	110.00	H34A—C34—H34B	110.00
O2—C16—H16A	110.00	H34A—C34—H34C	110.00
O2—C16—H16B	110.00	H34B—C34—H34C	110.00
C16—O2—C3—C2	−172.1 (5)	O4—C10—C11—C15	−0.9 (8)
C16—O2—C3—C4	8.5 (8)	C9—C10—C11—C12	−1.7 (9)
C3—O2—C16—C17	172.9 (5)	C9—C10—C11—C15	179.5 (6)
C33—O7—C20—C19	−167.2 (5)	C10—C11—C12—C13	0.4 (10)
C33—O7—C20—C21	13.5 (8)	C15—C11—C12—C13	179.1 (7)
C20—O7—C33—C34	179.8 (5)	C11—C12—C13—C14	1.1 (11)
C7—N1—N2—C8	178.4 (5)	C12—C13—C14—C9	−1.2 (10)
N2—N1—C7—C1	179.0 (5)	C23—C18—C19—O5	−179.8 (5)
N1—N2—C8—C9	178.1 (5)	C23—C18—C19—C20	−0.2 (8)
N1—N2—C8—O3	0.3 (8)	C24—C18—C19—O5	2.9 (8)
N4—N3—C24—C18	178.0 (4)	C24—C18—C19—C20	−177.5 (5)
C24—N3—N4—C25	−179.5 (5)	C19—C18—C23—C22	−0.5 (8)
N3—N4—C25—O6	1.6 (8)	C24—C18—C23—C22	176.9 (6)
N3—N4—C25—C26	−177.8 (4)	C19—C18—C24—N3	−0.2 (8)
C6—C1—C2—O1	−179.9 (5)	C23—C18—C24—N3	−177.6 (5)
C6—C1—C2—C3	2.5 (8)	O5—C19—C20—O7	0.5 (7)
C7—C1—C2—O1	1.8 (8)	O5—C19—C20—C21	179.8 (5)
C2—C1—C6—C5	1.4 (10)	C18—C19—C20—O7	−179.1 (5)
C7—C1—C6—C5	179.8 (6)	C18—C19—C20—C21	0.2 (8)
C7—C1—C2—C3	−175.9 (5)	O7—C20—C21—C22	179.6 (6)
C6—C1—C7—N1	−177.7 (6)	C19—C20—C21—C22	0.4 (9)
C2—C1—C7—N1	0.6 (8)	C20—C21—C22—C23	−1.1 (10)
C1—C2—C3—C4	−4.2 (8)	C21—C22—C23—C18	1.2 (10)
C1—C2—C3—O2	176.3 (5)	O6—C25—C26—C27	−5.2 (8)
O1—C2—C3—O2	−1.5 (7)	O6—C25—C26—C31	175.3 (5)
O1—C2—C3—C4	178.0 (5)	N4—C25—C26—C27	174.2 (5)
O2—C3—C4—C5	−178.4 (6)	N4—C25—C26—C31	−5.3 (8)
C2—C3—C4—C5	2.2 (10)	C25—C26—C27—O8	0.7 (8)
C3—C4—C5—C6	1.6 (12)	C25—C26—C27—C28	−179.3 (5)
C4—C5—C6—C1	−3.4 (11)	C31—C26—C27—O8	−179.8 (5)
O3—C8—C9—C10	−8.2 (9)	C31—C26—C27—C28	0.3 (8)
O3—C8—C9—C14	174.3 (6)	C25—C26—C31—C30	179.5 (6)
N2—C8—C9—C10	174.1 (5)	C27—C26—C31—C30	0.0 (8)
N2—C8—C9—C14	−3.4 (9)	O8—C27—C28—C29	179.9 (5)
C10—C9—C14—C13	−0.1 (9)	O8—C27—C28—C32	−1.3 (8)
C8—C9—C10—O4	4.4 (8)	C26—C27—C28—C29	−0.2 (9)
C8—C9—C10—C11	−176.0 (5)	C26—C27—C28—C32	178.7 (5)
C14—C9—C10—O4	−178.0 (5)	C27—C28—C29—C30	−0.2 (10)
C14—C9—C10—C11	1.6 (9)	C32—C28—C29—C30	−179.0 (6)
C8—C9—C14—C13	177.4 (6)	C28—C29—C30—C31	0.4 (10)
O4—C10—C11—C12	177.9 (6)	C29—C30—C31—C26	−0.3 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.84	2.558 (5)	145
O4—H4B···O3	0.82	1.83	2.549 (5)	145
O5—H5···N3	0.82	1.87	2.585 (6)	145
O8—H8···O6	0.85 (3)	1.75 (4)	2.536 (6)	152 (5)
N2—H2···O5i	0.90 (2)	2.22 (2)	3.035 (6)	150 (4)
N2—H2···O7i	0.90 (2)	2.52 (4)	3.218 (6)	134 (3)
N4—H4···O1	0.90 (4)	2.26 (3)	3.027 (5)	144 (5)
C7—H7···O5i	0.93	2.59	3.353 (7)	140
C14—H14···O5i	0.93	2.60	3.516 (7)	169
C24—H24···O1	0.93	2.45	3.261 (6)	145
C33—H33A···O6ii	0.97	2.58	3.420 (7)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.84	2.558 (5)	145
O4—H4B⋯O3	0.82	1.83	2.549 (5)	145
O5—H5⋯N3	0.82	1.87	2.585 (6)	145
O8—H8⋯O6	0.85 (3)	1.75 (4)	2.536 (6)	152 (5)
N2—H2⋯O5i	0.90 (2)	2.22 (2)	3.035 (6)	150 (4)
N2—H2⋯O7i	0.90 (2)	2.52 (4)	3.218 (6)	134 (3)
N4—H4⋯O1	0.90 (4)	2.26 (3)	3.027 (5)	144 (5)
C7—H7⋯O5i	0.93	2.59	3.353 (7)	140
C14—H14⋯O5i	0.93	2.60	3.516 (7)	169
C24—H24⋯O1	0.93	2.45	3.261 (6)	145
C33—H33A⋯O6ii	0.97	2.58	3.420 (7)	145

Symmetry codes: (i) ; (ii) .