(N',N''Z,N',N''E)-N',N''-[1-(4-Chloro-phen-yl)ethane-1,2-diyl-idene]bis-(3-methyl-1-benzofuran-2-carbohydrazide).

In the title compound, C(28)H(21)ClN(4)O(4), the benzofuran ring systems make dihedral angles of 7.43 (8) and 30.92 (9)° with the chloro-substituted benzene ring. The dihedral angle between the two benzofuran ring systems is 27.41 (7)°. The two benzofuran rings are connected to the chloro-substituted benzene ring through C-N-N=C and C-N-N=C-C bridges which are nearly planar [maximum deviations = 0.003 (1) and 0.037 (1) Å]. An intra-molecular N-H⋯N hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked by N-H⋯(O,N) and C-H⋯O hydrogen bonds into a tape along the c axis and these tapes are further connected by another weak C-H⋯O hydrogen bond into a sheet parallel to the bc plane. π-π inter-actions [centroid-to-centroid distances = 3.4845 (12)-3.6250 (13) Å] are also observed.

Related literature

For the biological activity of benzofurans, see: Abdel-Aziz et al. (2009 ▶); Abdel-Aziz & Mekawey (2009 ▶); Abdel-Wahab et al. (2009 ▶); Bhovi et al. (2010 ▶). For the synthesis, see: Abdel-Aziz et al. (2009 ▶). For n class="Chemical">hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C28H21ClN4O4

M = 512.94

Monoclinic,

a = 7.5539 (9) Å

b = 23.332 (3) Å

c = 13.6027 (16) Å

β = 94.275 (2)°

V = 2390.8 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 100 K

0.30 × 0.11 × 0.09 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.942, T max = 0.983

19379 measured reflections

6850 independent reflections

4662 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.144

S = 1.03

6850 reflections

344 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.49 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812030504/is5163sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030504/is5163Isup2.hkl

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

C28H21ClN4O4	F(000) = 1064
Mr = 512.94	Dx = 1.425 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4684 reflections
a = 7.5539 (9) Å	θ = 2.3–29.8°
b = 23.332 (3) Å	µ = 0.20 mm−1
c = 13.6027 (16) Å	T = 100 K
β = 94.275 (2)°	Block, colourless
V = 2390.8 (5) Å3	0.30 × 0.11 × 0.09 mm
Z = 4

Bruker APEX DUO CCD area-detector diffractometer	6850 independent reflections
Radiation source: fine-focus sealed tube	4662 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ and ω scans	θmax = 29.9°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→10
Tmin = 0.942, Tmax = 0.983	k = −32→28
19379 measured reflections	l = −18→18

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) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0696P)2 + 0.8585P] where P = (Fo2 + 2Fc2)/3
6850 reflections	(Δ/σ)max = 0.001
344 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.49 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Cl1	0.45030 (7)	0.51063 (2)	0.65612 (4)	0.02517 (13)
O1	−0.18297 (18)	0.91093 (5)	0.50974 (9)	0.0174 (3)
O2	0.0296 (2)	0.84287 (6)	0.72023 (9)	0.0260 (3)
O3	−0.26774 (18)	0.77075 (5)	0.10805 (9)	0.0182 (3)
O4	−0.1284 (2)	0.88213 (6)	0.27065 (10)	0.0275 (3)
N1	0.0177 (2)	0.81923 (6)	0.55642 (11)	0.0161 (3)
N2	0.1004 (2)	0.76847 (6)	0.57851 (11)	0.0161 (3)
N3	0.0059 (2)	0.78780 (7)	0.36930 (10)	0.0175 (3)
N4	−0.0473 (2)	0.78768 (7)	0.27125 (11)	0.0190 (3)
C1	−0.2346 (2)	0.96694 (8)	0.49610 (13)	0.0166 (4)
C2	−0.3267 (3)	0.98844 (8)	0.41213 (14)	0.0207 (4)
H2A	−0.3607	0.9653	0.3583	0.025*
C3	−0.3650 (3)	1.04656 (9)	0.41339 (15)	0.0238 (4)
H3A	−0.4277	1.0631	0.3591	0.029*
C4	−0.3112 (3)	1.08106 (9)	0.49488 (15)	0.0242 (4)
H4A	−0.3386	1.1199	0.4930	0.029*
C5	−0.2186 (3)	1.05869 (8)	0.57782 (15)	0.0211 (4)
H5A	−0.1820	1.0820	0.6310	0.025*
C6	−0.1818 (2)	0.99973 (8)	0.57888 (13)	0.0168 (4)
C7	−0.0928 (2)	0.96115 (8)	0.64901 (13)	0.0171 (4)
C8	−0.0978 (2)	0.90913 (8)	0.60363 (12)	0.0167 (4)
C9	−0.0134 (3)	0.85473 (8)	0.63364 (12)	0.0174 (4)
C10	0.1336 (2)	0.73377 (7)	0.50707 (12)	0.0154 (3)
C11	0.2211 (2)	0.67909 (8)	0.53963 (13)	0.0157 (3)
C12	0.2970 (3)	0.67412 (8)	0.63637 (13)	0.0212 (4)
H12A	0.3000	0.7059	0.6776	0.025*
C13	0.3677 (3)	0.62277 (8)	0.67172 (14)	0.0225 (4)
H13A	0.4167	0.6200	0.7363	0.027*
C14	0.3648 (3)	0.57558 (8)	0.60979 (14)	0.0195 (4)
C15	0.2966 (3)	0.57942 (8)	0.51350 (14)	0.0232 (4)
H15A	0.2980	0.5477	0.4721	0.028*
C16	0.2252 (3)	0.63126 (8)	0.47841 (14)	0.0205 (4)
H16A	0.1796	0.6340	0.4132	0.025*
C17	0.0845 (3)	0.74172 (8)	0.40184 (13)	0.0186 (4)
H17A	0.1104	0.7130	0.3576	0.022*
C18	−0.1258 (3)	0.83580 (8)	0.22966 (13)	0.0180 (4)
C19	−0.2064 (2)	0.82603 (8)	0.12888 (13)	0.0168 (4)
C20	−0.2279 (3)	0.86146 (8)	0.04978 (13)	0.0172 (4)
C21	−0.3092 (3)	0.82657 (8)	−0.02879 (13)	0.0188 (4)
C22	−0.3632 (3)	0.83616 (9)	−0.12821 (14)	0.0266 (4)
H22A	−0.3489	0.8719	−0.1570	0.032*
C23	−0.4381 (3)	0.79104 (10)	−0.18212 (15)	0.0328 (5)
H23A	−0.4758	0.7966	−0.2481	0.039*
C24	−0.4586 (3)	0.73683 (10)	−0.13934 (16)	0.0324 (5)
H24A	−0.5101	0.7074	−0.1777	0.039*
C25	−0.4041 (3)	0.72607 (9)	−0.04164 (15)	0.0257 (4)
H25A	−0.4157	0.6901	−0.0132	0.031*
C26	−0.3311 (2)	0.77218 (8)	0.01104 (13)	0.0189 (4)
C27	−0.1779 (3)	0.92302 (8)	0.04235 (15)	0.0252 (4)
H27A	−0.1037	0.9338	0.0997	0.038*
H27B	−0.2833	0.9462	0.0380	0.038*
H27C	−0.1146	0.9287	−0.0155	0.038*
C28	−0.0066 (3)	0.97664 (8)	0.74798 (14)	0.0230 (4)
H28A	0.0764	0.9473	0.7696	0.034*
H28B	−0.0956	0.9802	0.7944	0.034*
H28C	0.0549	1.0124	0.7435	0.034*
H1N1	−0.013 (3)	0.8287 (9)	0.4940 (17)	0.023 (6)*
H1N4	−0.033 (3)	0.7535 (12)	0.2352 (19)	0.043 (7)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0302 (3)	0.0151 (2)	0.0296 (2)	0.00422 (19)	−0.00130 (19)	0.00252 (17)
O1	0.0233 (7)	0.0133 (6)	0.0152 (6)	−0.0004 (5)	−0.0006 (5)	−0.0009 (5)
O2	0.0435 (9)	0.0199 (7)	0.0143 (6)	0.0074 (6)	0.0013 (6)	0.0017 (5)
O3	0.0223 (7)	0.0133 (6)	0.0182 (6)	−0.0003 (5)	−0.0025 (5)	−0.0016 (5)
O4	0.0436 (9)	0.0151 (7)	0.0226 (7)	0.0026 (6)	−0.0047 (6)	−0.0031 (5)
N1	0.0245 (8)	0.0101 (7)	0.0135 (7)	0.0008 (6)	−0.0003 (6)	−0.0001 (5)
N2	0.0192 (8)	0.0098 (7)	0.0191 (7)	0.0006 (6)	0.0004 (6)	0.0005 (5)
N3	0.0210 (8)	0.0174 (8)	0.0138 (7)	−0.0005 (6)	−0.0016 (6)	−0.0002 (5)
N4	0.0260 (9)	0.0158 (8)	0.0145 (7)	0.0032 (6)	−0.0027 (6)	−0.0025 (6)
C1	0.0168 (9)	0.0122 (8)	0.0209 (8)	−0.0009 (7)	0.0028 (7)	0.0002 (6)
C2	0.0196 (9)	0.0201 (10)	0.0222 (9)	−0.0016 (7)	0.0005 (7)	0.0025 (7)
C3	0.0198 (10)	0.0225 (10)	0.0289 (10)	0.0013 (8)	0.0005 (8)	0.0067 (8)
C4	0.0219 (10)	0.0138 (9)	0.0375 (11)	0.0032 (7)	0.0059 (8)	0.0039 (8)
C5	0.0197 (9)	0.0147 (9)	0.0293 (10)	−0.0006 (7)	0.0040 (8)	−0.0036 (7)
C6	0.0162 (9)	0.0149 (9)	0.0196 (8)	0.0002 (7)	0.0034 (7)	−0.0011 (6)
C7	0.0188 (9)	0.0143 (9)	0.0182 (8)	−0.0005 (7)	0.0022 (7)	−0.0011 (6)
C8	0.0207 (9)	0.0150 (9)	0.0143 (7)	−0.0012 (7)	0.0002 (7)	−0.0007 (6)
C9	0.0227 (10)	0.0133 (9)	0.0165 (8)	−0.0010 (7)	0.0029 (7)	−0.0017 (6)
C10	0.0161 (9)	0.0128 (8)	0.0169 (8)	−0.0015 (6)	−0.0006 (6)	−0.0005 (6)
C11	0.0147 (9)	0.0135 (8)	0.0188 (8)	−0.0010 (7)	0.0011 (6)	−0.0010 (6)
C12	0.0251 (10)	0.0177 (9)	0.0201 (8)	0.0024 (8)	−0.0033 (7)	−0.0046 (7)
C13	0.0264 (11)	0.0205 (10)	0.0197 (9)	0.0041 (8)	−0.0031 (7)	−0.0011 (7)
C14	0.0195 (9)	0.0132 (9)	0.0258 (9)	0.0008 (7)	0.0021 (7)	0.0018 (7)
C15	0.0301 (11)	0.0136 (9)	0.0257 (9)	0.0020 (8)	−0.0002 (8)	−0.0047 (7)
C16	0.0259 (10)	0.0164 (9)	0.0187 (8)	0.0005 (7)	−0.0022 (7)	−0.0019 (7)
C17	0.0231 (10)	0.0156 (9)	0.0168 (8)	0.0009 (7)	−0.0003 (7)	−0.0026 (6)
C18	0.0218 (9)	0.0151 (9)	0.0171 (8)	−0.0010 (7)	0.0014 (7)	−0.0016 (6)
C19	0.0199 (9)	0.0118 (8)	0.0183 (8)	−0.0003 (7)	−0.0005 (7)	−0.0029 (6)
C20	0.0190 (9)	0.0141 (9)	0.0184 (8)	0.0020 (7)	0.0007 (7)	−0.0009 (6)
C21	0.0198 (9)	0.0192 (10)	0.0172 (8)	0.0038 (7)	0.0005 (7)	−0.0011 (7)
C22	0.0363 (12)	0.0248 (11)	0.0181 (9)	0.0076 (9)	−0.0025 (8)	−0.0002 (7)
C23	0.0401 (13)	0.0350 (13)	0.0217 (9)	0.0093 (10)	−0.0093 (9)	−0.0075 (8)
C24	0.0343 (13)	0.0308 (12)	0.0300 (11)	0.0039 (9)	−0.0110 (9)	−0.0124 (9)
C25	0.0247 (10)	0.0205 (10)	0.0308 (10)	0.0002 (8)	−0.0049 (8)	−0.0062 (8)
C26	0.0171 (9)	0.0202 (9)	0.0187 (8)	0.0022 (7)	−0.0017 (7)	−0.0027 (7)
C27	0.0329 (12)	0.0168 (10)	0.0259 (9)	−0.0006 (8)	0.0031 (8)	0.0012 (7)
C28	0.0298 (11)	0.0191 (10)	0.0196 (8)	0.0000 (8)	−0.0007 (8)	−0.0060 (7)

Cl1—C14	1.7465 (19)	C11—C16	1.394 (2)
O1—C1	1.372 (2)	C11—C12	1.400 (2)
O1—C8	1.387 (2)	C12—C13	1.383 (3)
O2—C9	1.230 (2)	C12—H12A	0.9300
O3—C26	1.370 (2)	C13—C14	1.386 (3)
O3—C19	1.392 (2)	C13—H13A	0.9300
O4—C18	1.217 (2)	C14—C15	1.374 (3)
N1—N2	1.362 (2)	C15—C16	1.394 (3)
N1—C9	1.372 (2)	C15—H15A	0.9300
N1—H1N1	0.89 (2)	C16—H16A	0.9300
N2—C10	1.304 (2)	C17—H17A	0.9300
N3—C17	1.291 (2)	C18—C19	1.476 (2)
N3—N4	1.364 (2)	C19—C20	1.357 (2)
N4—C18	1.372 (2)	C20—C21	1.444 (3)
N4—H1N4	0.95 (3)	C20—C27	1.491 (3)
C1—C2	1.386 (3)	C21—C26	1.395 (3)
C1—C6	1.395 (2)	C21—C22	1.401 (3)
C2—C3	1.387 (3)	C22—C23	1.380 (3)
C2—H2A	0.9300	C22—H22A	0.9300
C3—C4	1.405 (3)	C23—C24	1.406 (3)
C3—H3A	0.9300	C23—H23A	0.9300
C4—C5	1.385 (3)	C24—C25	1.385 (3)
C4—H4A	0.9300	C24—H24A	0.9300
C5—C6	1.403 (3)	C25—C26	1.384 (3)
C5—H5A	0.9300	C25—H25A	0.9300
C6—C7	1.441 (2)	C27—H27A	0.9600
C7—C8	1.361 (2)	C27—H27B	0.9600
C7—C28	1.496 (2)	C27—H27C	0.9600
C8—C9	1.465 (3)	C28—H28A	0.9600
C10—C17	1.463 (2)	C28—H28B	0.9600
C10—C11	1.489 (2)	C28—H28C	0.9600
C1—O1—C8	105.12 (13)	C15—C14—Cl1	120.19 (15)
C26—O3—C19	105.10 (14)	C13—C14—Cl1	118.78 (14)
N2—N1—C9	117.26 (14)	C14—C15—C16	119.41 (17)
N2—N1—H1N1	120.4 (14)	C14—C15—H15A	120.3
C9—N1—H1N1	122.3 (14)	C16—C15—H15A	120.3
C10—N2—N1	119.09 (15)	C15—C16—C11	121.00 (17)
C17—N3—N4	115.35 (15)	C15—C16—H16A	119.5
N3—N4—C18	119.22 (15)	C11—C16—H16A	119.5
N3—N4—H1N4	118.1 (16)	N3—C17—C10	121.18 (16)
C18—N4—H1N4	122.6 (16)	N3—C17—H17A	119.4
O1—C1—C2	125.17 (16)	C10—C17—H17A	119.4
O1—C1—C6	110.60 (15)	O4—C18—N4	124.01 (16)
C2—C1—C6	124.24 (17)	O4—C18—C19	122.89 (17)
C1—C2—C3	115.84 (18)	N4—C18—C19	113.10 (15)
C1—C2—H2A	122.1	C20—C19—O3	112.62 (15)
C3—C2—H2A	122.1	C20—C19—C18	131.24 (17)
C2—C3—C4	121.44 (18)	O3—C19—C18	116.11 (15)
C2—C3—H3A	119.3	C19—C20—C21	105.23 (16)
C4—C3—H3A	119.3	C19—C20—C27	128.68 (17)
C5—C4—C3	121.71 (18)	C21—C20—C27	126.09 (16)
C5—C4—H4A	119.1	C26—C21—C22	119.06 (18)
C3—C4—H4A	119.1	C26—C21—C20	106.37 (15)
C4—C5—C6	117.75 (18)	C22—C21—C20	134.56 (19)
C4—C5—H5A	121.1	C23—C22—C21	118.0 (2)
C6—C5—H5A	121.1	C23—C22—H22A	121.0
C1—C6—C5	119.00 (17)	C21—C22—H22A	121.0
C1—C6—C7	106.45 (16)	C22—C23—C24	121.32 (19)
C5—C6—C7	134.54 (17)	C22—C23—H23A	119.3
C8—C7—C6	105.12 (15)	C24—C23—H23A	119.3
C8—C7—C28	128.27 (17)	C25—C24—C23	121.77 (19)
C6—C7—C28	126.54 (16)	C25—C24—H24A	119.1
C7—C8—O1	112.71 (16)	C23—C24—H24A	119.1
C7—C8—C9	130.51 (16)	C26—C25—C24	115.7 (2)
O1—C8—C9	116.43 (15)	C26—C25—H25A	122.1
O2—C9—N1	123.33 (17)	C24—C25—H25A	122.1
O2—C9—C8	122.71 (16)	O3—C26—C25	125.22 (18)
N1—C9—C8	113.93 (15)	O3—C26—C21	110.68 (16)
N2—C10—C17	126.98 (16)	C25—C26—C21	124.09 (17)
N2—C10—C11	114.60 (15)	C20—C27—H27A	109.5
C17—C10—C11	118.30 (15)	C20—C27—H27B	109.5
C16—C11—C12	117.99 (17)	H27A—C27—H27B	109.5
C16—C11—C10	122.49 (16)	C20—C27—H27C	109.5
C12—C11—C10	119.47 (16)	H27A—C27—H27C	109.5
C13—C12—C11	121.25 (17)	H27B—C27—H27C	109.5
C13—C12—H12A	119.4	C7—C28—H28A	109.5
C11—C12—H12A	119.4	C7—C28—H28B	109.5
C12—C13—C14	119.25 (17)	H28A—C28—H28B	109.5
C12—C13—H13A	120.4	C7—C28—H28C	109.5
C14—C13—H13A	120.4	H28A—C28—H28C	109.5
C15—C14—C13	121.03 (17)	H28B—C28—H28C	109.5
C9—N1—N2—C10	−179.44 (17)	C12—C13—C14—C15	1.5 (3)
C17—N3—N4—C18	−177.48 (17)	C12—C13—C14—Cl1	−178.68 (16)
C8—O1—C1—C2	−179.32 (19)	C13—C14—C15—C16	−1.7 (3)
C8—O1—C1—C6	0.6 (2)	Cl1—C14—C15—C16	178.55 (16)
O1—C1—C2—C3	−179.65 (18)	C14—C15—C16—C11	−0.3 (3)
C6—C1—C2—C3	0.5 (3)	C12—C11—C16—C15	2.4 (3)
C1—C2—C3—C4	0.6 (3)	C10—C11—C16—C15	−175.19 (18)
C2—C3—C4—C5	−0.4 (3)	N4—N3—C17—C10	−174.21 (16)
C3—C4—C5—C6	−0.9 (3)	N2—C10—C17—N3	3.1 (3)
O1—C1—C6—C5	178.29 (16)	C11—C10—C17—N3	178.91 (17)
C2—C1—C6—C5	−1.8 (3)	N3—N4—C18—O4	11.4 (3)
O1—C1—C6—C7	−0.6 (2)	N3—N4—C18—C19	−169.09 (16)
C2—C1—C6—C7	179.31 (18)	C26—O3—C19—C20	−0.2 (2)
C4—C5—C6—C1	2.0 (3)	C26—O3—C19—C18	−178.47 (16)
C4—C5—C6—C7	−179.5 (2)	O4—C18—C19—C20	31.0 (3)
C1—C6—C7—C8	0.4 (2)	N4—C18—C19—C20	−148.4 (2)
C5—C6—C7—C8	−178.3 (2)	O4—C18—C19—O3	−151.14 (19)
C1—C6—C7—C28	177.63 (19)	N4—C18—C19—O3	29.4 (2)
C5—C6—C7—C28	−1.0 (4)	O3—C19—C20—C21	−0.1 (2)
C6—C7—C8—O1	0.0 (2)	C18—C19—C20—C21	177.8 (2)
C28—C7—C8—O1	−177.21 (18)	O3—C19—C20—C27	−179.37 (18)
C6—C7—C8—C9	172.82 (19)	C18—C19—C20—C27	−1.5 (4)
C28—C7—C8—C9	−4.4 (4)	C19—C20—C21—C26	0.4 (2)
C1—O1—C8—C7	−0.4 (2)	C27—C20—C21—C26	179.71 (19)
C1—O1—C8—C9	−174.26 (16)	C19—C20—C21—C22	−178.8 (2)
N2—N1—C9—O2	0.1 (3)	C27—C20—C21—C22	0.5 (4)
N2—N1—C9—C8	178.22 (15)	C26—C21—C22—C23	0.8 (3)
C7—C8—C9—O2	24.7 (3)	C20—C21—C22—C23	180.0 (2)
O1—C8—C9—O2	−162.71 (18)	C21—C22—C23—C24	−0.6 (3)
C7—C8—C9—N1	−153.5 (2)	C22—C23—C24—C25	−0.3 (4)
O1—C8—C9—N1	19.1 (2)	C23—C24—C25—C26	0.9 (3)
N1—N2—C10—C17	−2.9 (3)	C19—O3—C26—C25	179.39 (19)
N1—N2—C10—C11	−178.84 (15)	C19—O3—C26—C21	0.5 (2)
N2—C10—C11—C16	162.87 (18)	C24—C25—C26—O3	−179.46 (19)
C17—C10—C11—C16	−13.4 (3)	C24—C25—C26—C21	−0.8 (3)
N2—C10—C11—C12	−14.7 (3)	C22—C21—C26—O3	178.77 (17)
C17—C10—C11—C12	169.01 (17)	C20—C21—C26—O3	−0.6 (2)
C16—C11—C12—C13	−2.5 (3)	C22—C21—C26—C25	−0.1 (3)
C10—C11—C12—C13	175.12 (18)	C20—C21—C26—C25	−179.49 (19)
C11—C12—C13—C14	0.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···N3	0.89 (2)	1.96 (2)	2.644 (2)	132.3 (18)
N4—H1N4···O2i	0.95 (3)	2.31 (3)	3.187 (2)	154 (2)
N4—H1N4···N2i	0.95 (3)	2.48 (3)	3.205 (2)	134 (2)
C17—H17A···O2i	0.93	2.32	3.165 (2)	150
C28—H28C···O4ii	0.96	2.53	3.464 (2)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯N3	0.89 (2)	1.96 (2)	2.644 (2)	132.3 (18)
N4—H1N4⋯O2i	0.95 (3)	2.31 (3)	3.187 (2)	154 (2)
N4—H1N4⋯N2i	0.95 (3)	2.48 (3)	3.205 (2)	134 (2)
C17—H17A⋯O2i	0.93	2.32	3.165 (2)	150
C28—H28C⋯O4ii	0.96	2.53	3.464 (2)	164

Symmetry codes: (i) ; (ii) .