(2E)-2-[(2-Hy-droxy-4-meth-oxy-phen-yl)(phen-yl)methyl-idene]-N-phenyl-hydrazinecarboxamide dimethyl-formamide monosolvate.

The title compound, C(21)H(19)N(3)O(3)·C(3)H(7)NO, adopts an E conformation with respect to the azomethine bond and crystallizes in the amide form. The dihedral angle between the rings lined to the C=N bond is 88.60 (12)°. The dimethyl-formamide solvent mol-ecule is disordered over two orientations with site occupancies of 0.684 (3) and 0.316 (3). The two N atoms of the hydrazinecarboxamide group are involved in inter-molecular N-H⋯O hydrogen bonds in which the dimethyl-formamide O atom acts as acceptor. The structure also features π-π inter-actions, with a centroid-centroid distance of 3.6561 (13) Å. Classical and non-classical intra-molecular O-H⋯N and C-H⋯O hydrogen bonds are also present.

Related literature

For applications of hydrazinecarboxamide and its derivatives, see: Afrasiabi et al. (2005 ▶); Alam et al. (2010 ▶). For related structures, see: Siji et al. (2010 ▶); Reena & Kurup (2010 ▶); Sithambaresan & Kurup (2011 ▶). For standard bond-length data, see: March (1992 ▶); Kala et al. (2007 ▶). For the synthesis, see: Sreekanth et al. (2004 ▶).

Experimental

Crystal data

C21H19N3O3·C3H7NO

M = 434.49

Monoclinic,

a = 13.1155 (7) Å

b = 16.9619 (11) Å

c = 10.7399 (5) Å

β = 105.509 (3)°

V = 2302.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.970, T max = 0.978

17400 measured reflections

4061 independent reflections

2875 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.158

S = 1.02

4061 reflections

311 parameters

10 restraints

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812017382/bv2201sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017382/bv2201Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812017382/bv2201Isup3.cml

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

C21H19N3O3·C3H7NO	F(000) = 920
Mr = 434.49	Dx = 1.254 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5896 reflections
a = 13.1155 (7) Å	θ = 2.4–28.2°
b = 16.9619 (11) Å	µ = 0.09 mm−1
c = 10.7399 (5) Å	T = 296 K
β = 105.509 (3)°	Block, colourless
V = 2302.2 (2) Å3	0.35 × 0.30 × 0.25 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4061 independent reflections
Radiation source: fine-focus sealed tube	2875 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
ω and φ scan	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −15→15
Tmin = 0.970, Tmax = 0.978	k = −19→20
17400 measured reflections	l = −12→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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0824P)2 + 0.2581P] where P = (Fo2 + 2Fc2)/3
4061 reflections	(Δ/σ)max < 0.001
311 parameters	Δρmax = 0.18 e Å−3
10 restraints	Δρmin = −0.19 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)
O1	0.84998 (10)	0.61778 (8)	1.04160 (12)	0.0666 (4)
H1	0.7974	0.6191	0.9700	0.100*
O2	1.21655 (11)	0.59166 (9)	1.18461 (13)	0.0740 (4)
O3	0.57307 (11)	0.63119 (10)	0.84928 (12)	0.0826 (5)
N1	0.75944 (12)	0.61397 (9)	0.79832 (14)	0.0588 (4)
N2	0.66741 (12)	0.61639 (10)	0.70205 (14)	0.0655 (5)
H2'	0.6700	0.6187	0.6222	0.079*
N3	0.48988 (12)	0.63420 (11)	0.63350 (14)	0.0663 (5)
H3'	0.5040	0.6304	0.5610	0.080*
C1	0.94202 (14)	0.60977 (10)	1.00767 (16)	0.0520 (4)
C2	1.03416 (15)	0.60499 (11)	1.10594 (16)	0.0581 (5)
H2	1.0311	0.6074	1.1914	0.070*
C3	1.13084 (14)	0.59664 (11)	1.07944 (17)	0.0559 (4)
C4	1.13607 (15)	0.59357 (12)	0.95264 (17)	0.0609 (5)
H4	1.2009	0.5881	0.9338	0.073*
C5	1.04372 (14)	0.59881 (11)	0.85454 (17)	0.0575 (5)
H5	1.0479	0.5971	0.7695	0.069*
C6	0.94474 (13)	0.60652 (10)	0.87711 (15)	0.0496 (4)
C7	0.84867 (14)	0.60951 (10)	0.76958 (16)	0.0509 (4)
C8	0.57499 (15)	0.62767 (12)	0.73737 (17)	0.0590 (5)
C9	0.38600 (14)	0.65561 (11)	0.63201 (16)	0.0561 (5)
C10	0.35631 (16)	0.68054 (13)	0.73941 (19)	0.0705 (6)
H10	0.4059	0.6834	0.8194	0.085*
C11	0.25230 (18)	0.70127 (14)	0.7270 (2)	0.0804 (6)
H11	0.2324	0.7176	0.7998	0.097*
C12	0.17775 (17)	0.69846 (14)	0.6102 (2)	0.0794 (6)
H12	0.1080	0.7128	0.6036	0.095*
C13	0.20729 (17)	0.67438 (15)	0.5040 (2)	0.0811 (6)
H13	0.1576	0.6724	0.4240	0.097*
C14	0.31036 (16)	0.65306 (14)	0.51496 (19)	0.0722 (6)
H14	0.3295	0.6365	0.4418	0.087*
C15	0.85612 (14)	0.60722 (11)	0.63283 (16)	0.0527 (4)
C16	0.85331 (16)	0.53656 (13)	0.57021 (17)	0.0710 (6)
H16	0.8457	0.4899	0.6124	0.085*
C17	0.86165 (18)	0.53419 (16)	0.4453 (2)	0.0847 (7)
H17	0.8602	0.4861	0.4033	0.102*
C18	0.87206 (17)	0.60280 (18)	0.3829 (2)	0.0831 (7)
H18	0.8780	0.6014	0.2986	0.100*
C19	0.87374 (19)	0.67305 (17)	0.4443 (2)	0.0896 (7)
H19	0.8803	0.7196	0.4012	0.108*
C20	0.86589 (17)	0.67617 (14)	0.56947 (19)	0.0748 (6)
H20	0.8672	0.7245	0.6109	0.090*
C21	1.31791 (17)	0.58519 (18)	1.1620 (2)	0.0898 (7)
H21A	1.3203	0.5388	1.1116	0.135*
H21B	1.3708	0.5815	1.2431	0.135*
H21C	1.3312	0.6309	1.1160	0.135*
O4A	0.5772 (14)	0.6210 (6)	0.4203 (10)	0.100 (2)	0.684 (3)
N4A	0.6036 (4)	0.59304 (18)	0.2263 (4)	0.0615 (10)	0.684 (3)
C22A	0.5958 (2)	0.5725 (2)	0.3396 (3)	0.0780 (9)	0.684 (3)
H22A	0.6043	0.5196	0.3627	0.094*	0.684 (3)
C23A	0.6011 (5)	0.6733 (3)	0.1866 (5)	0.1115 (15)	0.684 (3)
H23A	0.5797	0.7059	0.2481	0.167*	0.684 (3)
H23B	0.5517	0.6791	0.1032	0.167*	0.684 (3)
H23C	0.6703	0.6888	0.1818	0.167*	0.684 (3)
C24A	0.6284 (3)	0.5357 (2)	0.1380 (4)	0.0957 (11)	0.684 (3)
H24A	0.6188	0.4834	0.1672	0.144*	0.684 (3)
H24B	0.7005	0.5423	0.1356	0.144*	0.684 (3)
H24C	0.5822	0.5435	0.0530	0.144*	0.684 (3)
O4B	0.576 (3)	0.5968 (15)	0.421 (2)	0.100 (2)	0.316 (3)
N4B	0.6081 (12)	0.6247 (6)	0.2322 (10)	0.0615 (10)	0.316 (3)
C22B	0.5949 (5)	0.6475 (5)	0.3420 (6)	0.0780 (9)	0.316 (3)
H22B	0.5990	0.7008	0.3633	0.094*	0.316 (3)
C23B	0.6333 (13)	0.6804 (8)	0.1434 (12)	0.1115 (15)	0.316 (3)
H23D	0.6241	0.7331	0.1712	0.167*	0.316 (3)
H23E	0.5872	0.6720	0.0586	0.167*	0.316 (3)
H23F	0.7054	0.6731	0.1413	0.167*	0.316 (3)
C24B	0.5982 (9)	0.5433 (6)	0.1957 (9)	0.0957 (11)	0.316 (3)
H24D	0.5607	0.5157	0.2478	0.144*	0.316 (3)
H24E	0.6673	0.5207	0.2085	0.144*	0.316 (3)
H24F	0.5599	0.5390	0.1062	0.144*	0.316 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0586 (8)	0.0987 (11)	0.0499 (7)	0.0052 (6)	0.0275 (6)	−0.0003 (6)
O2	0.0609 (8)	0.1036 (11)	0.0558 (8)	0.0070 (7)	0.0124 (6)	0.0008 (7)
O3	0.0688 (9)	0.1380 (14)	0.0465 (8)	0.0131 (8)	0.0250 (6)	0.0061 (7)
N1	0.0527 (9)	0.0780 (11)	0.0483 (8)	0.0002 (7)	0.0181 (7)	−0.0024 (7)
N2	0.0509 (9)	0.1028 (13)	0.0464 (8)	0.0032 (8)	0.0191 (7)	−0.0020 (7)
N3	0.0544 (9)	0.1032 (13)	0.0464 (8)	0.0042 (8)	0.0224 (7)	−0.0056 (8)
C1	0.0570 (10)	0.0564 (11)	0.0489 (9)	−0.0002 (8)	0.0249 (8)	−0.0001 (7)
C2	0.0648 (12)	0.0707 (12)	0.0426 (9)	0.0019 (9)	0.0208 (8)	0.0010 (8)
C3	0.0565 (11)	0.0599 (11)	0.0506 (10)	0.0009 (8)	0.0132 (8)	0.0013 (8)
C4	0.0533 (11)	0.0763 (13)	0.0577 (11)	0.0004 (9)	0.0230 (9)	−0.0020 (9)
C5	0.0578 (11)	0.0731 (13)	0.0466 (9)	−0.0014 (9)	0.0224 (8)	−0.0018 (8)
C6	0.0557 (10)	0.0525 (10)	0.0446 (9)	−0.0014 (8)	0.0204 (8)	−0.0013 (7)
C7	0.0552 (10)	0.0554 (10)	0.0468 (9)	0.0004 (8)	0.0216 (8)	−0.0019 (7)
C8	0.0562 (11)	0.0774 (13)	0.0483 (10)	0.0011 (9)	0.0224 (8)	0.0005 (8)
C9	0.0541 (10)	0.0655 (12)	0.0545 (10)	−0.0016 (8)	0.0245 (8)	−0.0001 (8)
C10	0.0660 (12)	0.0894 (15)	0.0636 (12)	0.0022 (10)	0.0301 (10)	−0.0071 (10)
C11	0.0787 (15)	0.0872 (16)	0.0902 (15)	0.0045 (12)	0.0481 (13)	−0.0083 (12)
C12	0.0601 (13)	0.0776 (15)	0.1070 (18)	0.0068 (11)	0.0335 (13)	0.0089 (12)
C13	0.0610 (13)	0.0981 (18)	0.0811 (14)	0.0040 (11)	0.0138 (11)	0.0091 (12)
C14	0.0657 (13)	0.0950 (16)	0.0576 (11)	0.0047 (11)	0.0197 (10)	0.0009 (10)
C15	0.0483 (9)	0.0676 (12)	0.0453 (9)	0.0019 (8)	0.0180 (7)	−0.0003 (8)
C16	0.0888 (15)	0.0769 (14)	0.0508 (10)	0.0136 (11)	0.0248 (10)	0.0000 (9)
C17	0.0972 (17)	0.1058 (19)	0.0559 (12)	0.0201 (14)	0.0286 (11)	−0.0127 (12)
C18	0.0656 (13)	0.142 (2)	0.0486 (11)	−0.0003 (13)	0.0267 (10)	0.0035 (13)
C19	0.0954 (17)	0.113 (2)	0.0636 (13)	−0.0207 (14)	0.0274 (12)	0.0217 (13)
C20	0.0877 (15)	0.0799 (15)	0.0613 (12)	−0.0139 (11)	0.0276 (10)	0.0036 (10)
C21	0.0567 (13)	0.134 (2)	0.0743 (14)	0.0100 (13)	0.0106 (10)	−0.0093 (13)
O4A	0.0932 (13)	0.156 (7)	0.0592 (9)	0.019 (6)	0.0347 (9)	−0.010 (3)
N4A	0.0719 (13)	0.064 (3)	0.0525 (11)	−0.004 (3)	0.0242 (10)	−0.004 (2)
C22A	0.0719 (17)	0.115 (3)	0.0520 (14)	0.0056 (19)	0.0260 (13)	0.0029 (17)
C23A	0.146 (5)	0.099 (3)	0.099 (4)	0.018 (3)	0.048 (3)	0.018 (3)
C24A	0.122 (3)	0.103 (3)	0.073 (2)	−0.008 (2)	0.045 (2)	−0.022 (2)
O4B	0.0932 (13)	0.156 (7)	0.0592 (9)	0.019 (6)	0.0347 (9)	−0.010 (3)
N4B	0.0719 (13)	0.064 (3)	0.0525 (11)	−0.004 (3)	0.0242 (10)	−0.004 (2)
C22B	0.0719 (17)	0.115 (3)	0.0520 (14)	0.0056 (19)	0.0260 (13)	0.0029 (17)
C23B	0.146 (5)	0.099 (3)	0.099 (4)	0.018 (3)	0.048 (3)	0.018 (3)
C24B	0.122 (3)	0.103 (3)	0.073 (2)	−0.008 (2)	0.045 (2)	−0.022 (2)

O1—C1	1.3579 (19)	C15—C20	1.376 (3)
O1—H1	0.8851	C16—C17	1.376 (3)
O2—C3	1.367 (2)	C16—H16	0.9300
O2—C21	1.418 (2)	C17—C18	1.368 (3)
O3—C8	1.210 (2)	C17—H17	0.9300
N1—C7	1.290 (2)	C18—C19	1.359 (4)
N1—N2	1.364 (2)	C18—H18	0.9300
N2—C8	1.377 (2)	C19—C20	1.376 (3)
N2—H2'	0.8683	C19—H19	0.9300
N3—C8	1.355 (2)	C20—H20	0.9300
N3—C9	1.406 (2)	C21—H21A	0.9600
N3—H3'	0.8495	C21—H21B	0.9600
C1—C2	1.378 (3)	C21—H21C	0.9600
C1—C6	1.413 (2)	O4A—C22A	1.265 (10)
C2—C3	1.379 (2)	N4A—C22A	1.295 (4)
C2—H2	0.9300	N4A—C23A	1.424 (6)
C3—C4	1.383 (2)	N4A—C24A	1.455 (5)
C4—C5	1.379 (3)	C22A—H22A	0.9300
C4—H4	0.9300	C23A—H23A	0.9600
C5—C6	1.389 (2)	C23A—H23B	0.9600
C5—H5	0.9300	C23A—H23C	0.9600
C6—C7	1.465 (2)	C24A—H24A	0.9600
C7—C15	1.498 (2)	C24A—H24B	0.9600
C9—C14	1.378 (3)	C24A—H24C	0.9600
C9—C10	1.379 (2)	O4B—C22B	1.274 (11)
C10—C11	1.380 (3)	N4B—C22B	1.295 (10)
C10—H10	0.9300	N4B—C24B	1.432 (10)
C11—C12	1.369 (3)	N4B—C23B	1.442 (11)
C11—H11	0.9300	C22B—H22B	0.9300
C12—C13	1.362 (3)	C23B—H23D	0.9600
C12—H12	0.9300	C23B—H23E	0.9600
C13—C14	1.374 (3)	C23B—H23F	0.9600
C13—H13	0.9300	C24B—H24D	0.9600
C14—H14	0.9300	C24B—H24E	0.9600
C15—C16	1.370 (3)	C24B—H24F	0.9600
C1—O1—H1	108.1	C9—C14—H14	119.3
C3—O2—C21	117.70 (15)	C16—C15—C20	119.64 (17)
C7—N1—N2	119.74 (14)	C16—C15—C7	120.25 (16)
N1—N2—C8	117.46 (14)	C20—C15—C7	120.11 (17)
N1—N2—H2'	119.3	C15—C16—C17	120.4 (2)
C8—N2—H2'	122.4	C15—C16—H16	119.8
C8—N3—C9	127.79 (14)	C17—C16—H16	119.8
C8—N3—H3'	114.5	C18—C17—C16	119.8 (2)
C9—N3—H3'	117.2	C18—C17—H17	120.1
O1—C1—C2	117.44 (14)	C16—C17—H17	120.1
O1—C1—C6	122.02 (16)	C19—C18—C17	119.97 (19)
C2—C1—C6	120.54 (15)	C19—C18—H18	120.0
C1—C2—C3	120.95 (15)	C17—C18—H18	120.0
C1—C2—H2	119.5	C18—C19—C20	120.8 (2)
C3—C2—H2	119.5	C18—C19—H19	119.6
O2—C3—C2	115.74 (15)	C20—C19—H19	119.6
O2—C3—C4	124.42 (16)	C15—C20—C19	119.4 (2)
C2—C3—C4	119.85 (17)	C15—C20—H20	120.3
C5—C4—C3	119.02 (16)	C19—C20—H20	120.3
C5—C4—H4	120.5	O2—C21—H21A	109.5
C3—C4—H4	120.5	O2—C21—H21B	109.5
C4—C5—C6	122.93 (15)	H21A—C21—H21B	109.5
C4—C5—H5	118.5	O2—C21—H21C	109.5
C6—C5—H5	118.5	H21A—C21—H21C	109.5
C5—C6—C1	116.71 (16)	H21B—C21—H21C	109.5
C5—C6—C7	120.84 (14)	C22A—N4A—C23A	122.5 (4)
C1—C6—C7	122.44 (15)	C22A—N4A—C24A	121.3 (3)
N1—C7—C6	117.22 (14)	C23A—N4A—C24A	115.8 (4)
N1—C7—C15	122.50 (15)	O4A—C22A—N4A	123.1 (5)
C6—C7—C15	120.28 (14)	O4A—C22A—H22A	118.4
O3—C8—N3	125.60 (16)	N4A—C22A—H22A	118.4
O3—C8—N2	122.28 (17)	C22B—N4B—C24B	120.9 (10)
N3—C8—N2	112.12 (14)	C22B—N4B—C23B	121.1 (9)
C14—C9—C10	118.51 (17)	C24B—N4B—C23B	118.0 (9)
C14—C9—N3	117.47 (15)	O4B—C22B—N4B	119.8 (14)
C10—C9—N3	124.01 (17)	O4B—C22B—H22B	120.1
C9—C10—C11	119.4 (2)	N4B—C22B—H22B	120.1
C9—C10—H10	120.3	N4B—C23B—H23D	109.5
C11—C10—H10	120.3	N4B—C23B—H23E	109.5
C12—C11—C10	121.66 (19)	H23D—C23B—H23E	109.5
C12—C11—H11	119.2	N4B—C23B—H23F	109.5
C10—C11—H11	119.2	H23D—C23B—H23F	109.5
C13—C12—C11	118.96 (19)	H23E—C23B—H23F	109.5
C13—C12—H12	120.5	N4B—C24B—H24D	109.5
C11—C12—H12	120.5	N4B—C24B—H24E	109.5
C12—C13—C14	120.1 (2)	H24D—C24B—H24E	109.5
C12—C13—H13	120.0	N4B—C24B—H24F	109.5
C14—C13—H13	120.0	H24D—C24B—H24F	109.5
C13—C14—C9	121.45 (18)	H24E—C24B—H24F	109.5
C13—C14—H14	119.3
C7—N1—N2—C8	−174.78 (16)	C8—N3—C9—C14	−175.6 (2)
O1—C1—C2—C3	179.87 (16)	C8—N3—C9—C10	5.9 (3)
C6—C1—C2—C3	−0.3 (3)	C14—C9—C10—C11	0.7 (3)
C21—O2—C3—C2	−178.32 (18)	N3—C9—C10—C11	179.1 (2)
C21—O2—C3—C4	1.9 (3)	C9—C10—C11—C12	−0.6 (3)
C1—C2—C3—O2	−179.31 (16)	C10—C11—C12—C13	0.2 (4)
C1—C2—C3—C4	0.5 (3)	C11—C12—C13—C14	0.3 (4)
O2—C3—C4—C5	179.65 (17)	C12—C13—C14—C9	−0.2 (4)
C2—C3—C4—C5	−0.1 (3)	C10—C9—C14—C13	−0.3 (3)
C3—C4—C5—C6	−0.5 (3)	N3—C9—C14—C13	−178.8 (2)
C4—C5—C6—C1	0.7 (3)	N1—C7—C15—C16	−89.3 (2)
C4—C5—C6—C7	−178.17 (17)	C6—C7—C15—C16	90.6 (2)
O1—C1—C6—C5	179.55 (16)	N1—C7—C15—C20	90.7 (2)
C2—C1—C6—C5	−0.3 (2)	C6—C7—C15—C20	−89.4 (2)
O1—C1—C6—C7	−1.6 (3)	C20—C15—C16—C17	0.9 (3)
C2—C1—C6—C7	178.53 (17)	C7—C15—C16—C17	−179.07 (18)
N2—N1—C7—C6	−179.56 (15)	C15—C16—C17—C18	−0.5 (3)
N2—N1—C7—C15	0.3 (3)	C16—C17—C18—C19	−0.2 (4)
C5—C6—C7—N1	177.65 (16)	C17—C18—C19—C20	0.5 (4)
C1—C6—C7—N1	−1.2 (2)	C16—C15—C20—C19	−0.6 (3)
C5—C6—C7—C15	−2.2 (3)	C7—C15—C20—C19	179.34 (19)
C1—C6—C7—C15	178.97 (15)	C18—C19—C20—C15	−0.1 (3)
C9—N3—C8—O3	8.5 (3)	C23A—N4A—C22A—O4A	5.7 (12)
C9—N3—C8—N2	−171.40 (18)	C24A—N4A—C22A—O4A	178.0 (10)
N1—N2—C8—O3	−3.9 (3)	C24B—N4B—C22B—O4B	2 (3)
N1—N2—C8—N3	175.94 (16)	C23B—N4B—C22B—O4B	−178 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.89	1.78	2.5655 (18)	147
N2—H2′···O4A	0.87	2.19	2.941 (12)	145
N2—H2′···O4B	0.87	2.22	2.96 (3)	143
N3—H3′···O4A	0.85	2.00	2.830 (7)	165
N3—H3′···O4B	0.85	2.07	2.882 (18)	161
C24A—H24C···O3i	0.96	2.62	3.400 (4)	139
C23B—H23E···O3i	0.96	2.31	3.157 (13)	147
C23B—H23F···O1i	0.96	2.59	3.473 (13)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.89	1.78	2.5655 (18)	147
N2—H2′⋯O4A	0.87	2.19	2.941 (12)	145
N2—H2′⋯O4B	0.87	2.22	2.96 (3)	143
N3—H3′⋯O4A	0.85	2.00	2.830 (7)	165
N3—H3′⋯O4B	0.85	2.07	2.882 (18)	161
C24A—H24C⋯O3i	0.96	2.62	3.400 (4)	139
C23B—H23E⋯O3i	0.96	2.31	3.157 (13)	147
C23B—H23F⋯O1i	0.96	2.59	3.473 (13)	153

Symmetry code: (i) .