2-(1,3-Dioxoisoindolin-2-yl)acetic acid-N'-[(E)-4-meth-oxy-benzyl-idene]pyridine-4-carbohydrazide (2/1).

In the crystal structure of the title compound, 2C(10)H(7)NO(4)·C(14)H(13)N(3)O(2), the two independent acid mol-ecules are connected through strong O-H⋯N and O-H⋯O hydrogen bonds to the central mol-ecule of the anti-tubercular drug N'-[(E)-4-meth-oxy-benzyl-idene]pyridine-4-carbohydrazide. Two such trimolecular units related by an inversion centre inter-act through a pair of N-H⋯O hydrogen bonds, forming a 3 + 3 mol-ecular aggregate. The dihedral angle between the aromatic rings of the hydrazone mol-ecule is 1.99 (12)°. The crystal packing features weak C-H⋯O and π-π stacking inter-actions, with centroid-centroid distances of 3.8460 (19) and 3.8703 (13) Å.

Related literature

For anti-tuberculosis drugs containing the isoniazid core structure, see: Bijev (2006 ▶); Imramovský et al. (2007 ▶); Maccari et al. (2005 ▶); Schultheiss & n class="Chemical">Newman (2009 ▶); Shindikar & Viswanathan (2005 ▶); Sinha et al. (2005 ▶). For crystal structures with N′-[(E)-(4-meth­oxy­phen­yl)methyl­idene]pyridine-4-carbo­hydrazide, see: Jing et al. (2005 ▶); Lin & Liu (2007 ▶); Shanmuga Sundara Raj et al. (1999 ▶); Wardell et al. (2007 ▶). For crystal structures with 2-(1,3-dioxoisoindolin-2-yl)acetic acid, see: Barooah et al. (2006 ▶); Feeder & Jones (1994 ▶, 1996 ▶). For a related co-crystal, see: Mohamed et al. (2012 ▶). For the synthesis of 2-(1,3-dioxoisoindolin-2-yl)acetic acid, see: Rajpurohit & Sah (2005 ▶).

Experimental

Crystal data

2C10H7NO4·C14n class="Species">H13N3O2

M = 665.61

Triclinic,

a = 8.1238 (4) Å

b = 12.7963 (7) Å

c = 15.9191 (11) Å

α = 105.590 (5)°

β = 101.160 (5)°

γ = 97.535 (4)°

V = 1534.19 (17) Å3

Z = 2

Cu Kα radiation

μ = 0.91 mm−1

T = 293 K

0.16 × 0.10 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur (Sapphire3, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.963, T max = 1.000

10334 measured reflections

5912 independent reflections

4836 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.116

S = 1.06

5912 reflections

456 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶), PLATON (Spek, 2009 ▶) and PARST (n class="Chemical">Nardelli, 1995 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812038032/rz2799sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038032/rz2799Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812038032/rz2799Isup3.cml

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

2C10H7NO4·C14H13N3O2	Z = 2
Mr = 665.61	F(000) = 692
Triclinic, P1	Dx = 1.441 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 8.1238 (4) Å	Cell parameters from 3871 reflections
b = 12.7963 (7) Å	θ = 3.0–72.3°
c = 15.9191 (11) Å	µ = 0.91 mm−1
α = 105.590 (5)°	T = 293 K
β = 101.160 (5)°	Prismatic, yellow
γ = 97.535 (4)°	0.16 × 0.10 × 0.08 mm
V = 1534.19 (17) Å3

Oxford Diffraction Xcalibur (Sapphire3, Gemini) diffractometer	5912 independent reflections
Radiation source: Enhance (Cu) X-ray Source	4836 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 16.3280 pixels mm-1	θmax = 72.5°, θmin = 3.0°
ω scans	h = −6→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −15→15
Tmin = 0.963, Tmax = 1.000	l = −19→19
10334 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.0523P)2 + 0.272P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
5912 reflections	Δρmax = 0.28 e Å−3
456 parameters	Δρmin = −0.21 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0024 (3)

Experimental. Absorption correction: Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. 'CrysAlisPro, (Oxford Diffraction, 2009)'

	x	y	z	Uiso*/Ueq
C1	−0.2642 (2)	0.95037 (14)	0.17010 (12)	0.0549 (4)
H1	−0.3093	0.9940	0.1368	0.066*
C2	−0.1425 (2)	1.00139 (13)	0.24952 (11)	0.0493 (4)
H2	−0.1069	1.0778	0.2689	0.059*
C3	−0.07405 (18)	0.93782 (11)	0.30007 (9)	0.0366 (3)
C4	−0.1314 (2)	0.82441 (12)	0.26761 (11)	0.0451 (4)
H4	−0.0881	0.7786	0.2992	0.054*
C5	−0.2535 (2)	0.78039 (13)	0.18774 (11)	0.0508 (4)
H5	−0.2915	0.7041	0.1667	0.061*
C6	0.05450 (18)	0.99688 (11)	0.38761 (9)	0.0367 (3)
C7	0.33689 (19)	0.92085 (12)	0.54388 (10)	0.0401 (3)
H7	0.3112	0.8449	0.5156	0.048*
C8	0.46634 (18)	0.96649 (12)	0.62817 (9)	0.0384 (3)
C9	0.5239 (2)	1.08025 (13)	0.66447 (11)	0.0495 (4)
H9	0.4785	1.1271	0.6346	0.059*
C10	0.6462 (2)	1.12434 (13)	0.74335 (12)	0.0534 (4)
H10	0.6852	1.2005	0.7656	0.064*
C11	0.7124 (2)	1.05611 (13)	0.79041 (10)	0.0440 (3)
C12	0.6576 (2)	0.94290 (13)	0.75570 (11)	0.0479 (4)
H12	0.7014	0.8965	0.7865	0.057*
C13	0.5365 (2)	0.89881 (13)	0.67442 (11)	0.0455 (4)
H13	0.5017	0.8225	0.6505	0.055*
C14	0.8949 (3)	1.04657 (17)	0.92371 (12)	0.0657 (5)
H14A	0.8023	1.0151	0.9443	0.099*
H14B	0.9823	1.0934	0.9744	0.099*
H14C	0.9415	0.9884	0.8901	0.099*
N1	−0.31974 (17)	0.84128 (11)	0.13922 (9)	0.0491 (3)
N2	0.13864 (16)	0.93389 (10)	0.42826 (8)	0.0406 (3)
N3	0.25843 (15)	0.98456 (10)	0.50851 (8)	0.0406 (3)
O1	0.07630 (14)	1.09815 (8)	0.41843 (7)	0.0474 (3)
O2	0.83335 (17)	1.11023 (10)	0.86773 (8)	0.0597 (3)
C1A	−0.5342 (2)	0.78299 (14)	−0.07334 (12)	0.0535 (4)
C2A	−0.6544 (2)	0.71923 (15)	−0.16347 (11)	0.0555 (4)
H2A1	−0.6875	0.7711	−0.1952	0.067*
H2A2	−0.5940	0.6709	−0.1989	0.067*
C3A	−0.8216 (2)	0.54517 (13)	−0.15390 (10)	0.0475 (4)
C4A	−0.9875 (2)	0.51700 (15)	−0.13116 (11)	0.0511 (4)
C5A	−1.0643 (3)	0.42141 (17)	−0.11908 (12)	0.0647 (5)
H5A	−1.0149	0.3590	−0.1273	0.078*
C6A	−1.2187 (3)	0.4222 (2)	−0.09410 (14)	0.0840 (7)
H6A	−1.2740	0.3594	−0.0848	0.101*
C7A	−1.2915 (3)	0.5161 (3)	−0.08276 (16)	0.0940 (9)
H7A	−1.3951	0.5146	−0.0660	0.113*
C8A	−1.2142 (3)	0.6116 (3)	−0.09567 (15)	0.0828 (7)
H8A	−1.2638	0.6739	−0.0882	0.099*
C9A	−1.0608 (2)	0.61061 (17)	−0.11997 (11)	0.0585 (5)
C10A	−0.9459 (2)	0.69870 (15)	−0.13613 (11)	0.0569 (4)
N1A	−0.80682 (17)	0.65359 (11)	−0.15608 (9)	0.0493 (3)
O1A	−0.4285 (3)	0.85939 (17)	−0.06654 (12)	0.1289 (9)
O2A	−0.55221 (17)	0.74356 (11)	−0.00883 (8)	0.0626 (4)
O3A	−0.71648 (17)	0.48833 (10)	−0.16856 (10)	0.0637 (3)
O4A	−0.9621 (2)	0.79203 (12)	−0.13410 (10)	0.0829 (5)
C1B	0.40479 (19)	1.30491 (12)	0.57084 (10)	0.0425 (3)
C2B	0.5016 (2)	1.37468 (13)	0.66499 (10)	0.0454 (4)
H2B1	0.4301	1.4222	0.6920	0.054*
H2B2	0.5286	1.3267	0.7015	0.054*
C3B	0.67039 (19)	1.55202 (12)	0.66280 (10)	0.0405 (3)
C4B	0.83781 (19)	1.58248 (12)	0.64317 (10)	0.0395 (3)
C5B	0.9136 (2)	1.67982 (13)	0.63322 (11)	0.0470 (4)
H5B	0.8603	1.7406	0.6396	0.056*
C6B	1.0719 (2)	1.68341 (15)	0.61333 (12)	0.0538 (4)
H6B	1.1261	1.7478	0.6059	0.065*
C7B	1.1523 (2)	1.59280 (16)	0.60421 (11)	0.0544 (4)
H7B	1.2594	1.5979	0.5913	0.065*
C8B	1.0751 (2)	1.49488 (14)	0.61414 (11)	0.0492 (4)
H8B	1.1285	1.4342	0.6082	0.059*
C9B	0.91670 (19)	1.49099 (12)	0.63309 (9)	0.0401 (3)
C10B	0.7997 (2)	1.39932 (12)	0.64460 (10)	0.0422 (3)
N1B	0.65796 (16)	1.44176 (10)	0.66338 (9)	0.0422 (3)
O1B	0.45570 (17)	1.30518 (12)	0.50517 (8)	0.0671 (4)
O2B	0.26246 (15)	1.24440 (9)	0.57228 (8)	0.0516 (3)
O3B	0.56253 (15)	1.60611 (10)	0.67685 (9)	0.0556 (3)
O4B	0.81814 (16)	1.30561 (9)	0.63963 (8)	0.0569 (3)
H1OA	−0.464 (3)	0.784 (2)	0.0486 (18)	0.101 (8)*
H1OB	0.210 (3)	1.1927 (18)	0.5169 (16)	0.078 (7)*
H1N2	0.126 (2)	0.8633 (16)	0.4029 (13)	0.056 (5)*

	U11	U22	U33	U12	U13	U23
C1	0.0628 (11)	0.0486 (9)	0.0472 (9)	0.0083 (8)	−0.0060 (8)	0.0194 (7)
C2	0.0578 (10)	0.0374 (8)	0.0453 (9)	0.0048 (7)	−0.0030 (7)	0.0135 (7)
C3	0.0358 (7)	0.0373 (7)	0.0347 (7)	0.0062 (6)	0.0053 (6)	0.0102 (6)
C4	0.0475 (9)	0.0371 (7)	0.0457 (8)	0.0063 (6)	−0.0004 (7)	0.0135 (6)
C5	0.0539 (9)	0.0381 (8)	0.0491 (9)	0.0017 (7)	−0.0016 (7)	0.0077 (7)
C6	0.0367 (7)	0.0350 (7)	0.0358 (7)	0.0037 (6)	0.0059 (6)	0.0098 (6)
C7	0.0418 (8)	0.0365 (7)	0.0397 (8)	0.0067 (6)	0.0058 (6)	0.0110 (6)
C8	0.0379 (7)	0.0409 (8)	0.0365 (7)	0.0083 (6)	0.0067 (6)	0.0129 (6)
C9	0.0550 (9)	0.0395 (8)	0.0492 (9)	0.0098 (7)	−0.0045 (7)	0.0169 (7)
C10	0.0605 (10)	0.0387 (8)	0.0508 (9)	0.0060 (7)	−0.0050 (8)	0.0112 (7)
C11	0.0446 (8)	0.0473 (8)	0.0365 (8)	0.0084 (7)	0.0030 (6)	0.0117 (6)
C12	0.0550 (9)	0.0477 (9)	0.0421 (8)	0.0130 (7)	0.0021 (7)	0.0207 (7)
C13	0.0522 (9)	0.0382 (8)	0.0437 (8)	0.0076 (7)	0.0047 (7)	0.0138 (6)
C14	0.0744 (13)	0.0714 (12)	0.0439 (10)	0.0109 (10)	−0.0080 (9)	0.0223 (9)
N1	0.0493 (8)	0.0489 (8)	0.0396 (7)	0.0038 (6)	−0.0030 (6)	0.0103 (6)
N2	0.0432 (7)	0.0340 (6)	0.0364 (6)	0.0068 (5)	−0.0026 (5)	0.0063 (5)
N3	0.0396 (6)	0.0400 (6)	0.0358 (6)	0.0054 (5)	−0.0006 (5)	0.0088 (5)
O1	0.0505 (6)	0.0348 (5)	0.0468 (6)	0.0030 (4)	−0.0050 (5)	0.0100 (5)
O2	0.0673 (8)	0.0539 (7)	0.0438 (6)	0.0057 (6)	−0.0126 (5)	0.0126 (5)
C1A	0.0593 (10)	0.0482 (9)	0.0460 (9)	−0.0015 (8)	0.0067 (8)	0.0126 (7)
C2A	0.0667 (11)	0.0522 (9)	0.0428 (9)	0.0047 (8)	0.0062 (8)	0.0147 (7)
C3A	0.0489 (9)	0.0448 (8)	0.0397 (8)	0.0092 (7)	−0.0003 (7)	0.0055 (7)
C4A	0.0451 (9)	0.0580 (10)	0.0373 (8)	0.0054 (7)	−0.0017 (7)	0.0034 (7)
C5A	0.0617 (11)	0.0676 (12)	0.0490 (10)	−0.0037 (9)	0.0045 (8)	0.0058 (9)
C6A	0.0640 (13)	0.1115 (19)	0.0524 (12)	−0.0225 (13)	0.0051 (10)	0.0102 (12)
C7A	0.0479 (12)	0.154 (3)	0.0619 (14)	0.0113 (15)	0.0099 (10)	0.0095 (15)
C8A	0.0557 (12)	0.121 (2)	0.0680 (14)	0.0321 (13)	0.0120 (10)	0.0173 (13)
C9A	0.0498 (10)	0.0750 (12)	0.0404 (9)	0.0219 (9)	−0.0015 (7)	0.0044 (8)
C10A	0.0659 (11)	0.0573 (10)	0.0384 (8)	0.0239 (9)	−0.0017 (8)	0.0038 (7)
N1A	0.0500 (8)	0.0448 (7)	0.0424 (7)	0.0095 (6)	−0.0027 (6)	0.0053 (6)
O1A	0.1529 (18)	0.1220 (15)	0.0688 (10)	−0.0829 (14)	−0.0089 (11)	0.0354 (10)
O2A	0.0641 (8)	0.0649 (8)	0.0428 (7)	−0.0146 (6)	−0.0080 (6)	0.0175 (6)
O3A	0.0600 (8)	0.0566 (7)	0.0794 (9)	0.0226 (6)	0.0205 (7)	0.0204 (7)
O4A	0.1137 (13)	0.0643 (9)	0.0734 (10)	0.0459 (9)	0.0155 (9)	0.0164 (7)
C1B	0.0432 (8)	0.0369 (7)	0.0429 (8)	0.0079 (6)	0.0024 (6)	0.0103 (6)
C2B	0.0483 (9)	0.0400 (8)	0.0426 (8)	0.0018 (6)	0.0056 (7)	0.0108 (6)
C3B	0.0431 (8)	0.0367 (7)	0.0374 (7)	0.0087 (6)	0.0009 (6)	0.0096 (6)
C4B	0.0410 (8)	0.0365 (7)	0.0358 (7)	0.0082 (6)	0.0000 (6)	0.0085 (6)
C5B	0.0493 (9)	0.0408 (8)	0.0484 (9)	0.0073 (7)	0.0037 (7)	0.0155 (7)
C6B	0.0514 (9)	0.0533 (9)	0.0506 (9)	−0.0018 (7)	0.0043 (7)	0.0170 (8)
C7B	0.0390 (8)	0.0720 (11)	0.0448 (9)	0.0057 (8)	0.0031 (7)	0.0130 (8)
C8B	0.0434 (8)	0.0551 (9)	0.0424 (8)	0.0167 (7)	0.0002 (7)	0.0076 (7)
C9B	0.0411 (8)	0.0378 (7)	0.0333 (7)	0.0088 (6)	−0.0035 (6)	0.0057 (6)
C10B	0.0465 (8)	0.0359 (7)	0.0356 (7)	0.0095 (6)	−0.0036 (6)	0.0056 (6)
N1B	0.0421 (7)	0.0339 (6)	0.0445 (7)	0.0049 (5)	0.0015 (5)	0.0092 (5)
O1B	0.0629 (8)	0.0824 (9)	0.0427 (7)	−0.0045 (7)	0.0081 (6)	0.0092 (6)
O2B	0.0517 (7)	0.0436 (6)	0.0470 (6)	−0.0037 (5)	0.0027 (5)	0.0058 (5)
O3B	0.0522 (7)	0.0508 (7)	0.0704 (8)	0.0220 (5)	0.0183 (6)	0.0208 (6)
O4B	0.0673 (8)	0.0347 (6)	0.0633 (7)	0.0158 (5)	0.0027 (6)	0.0124 (5)

C1—N1	1.332 (2)	C3A—N1A	1.387 (2)
C1—C2	1.380 (2)	C3A—C4A	1.486 (2)
C1—H1	0.9300	C4A—C5A	1.377 (3)
C2—C3	1.384 (2)	C4A—C9A	1.391 (3)
C2—H2	0.9300	C5A—C6A	1.388 (3)
C3—C4	1.384 (2)	C5A—H5A	0.9300
C3—C6	1.5058 (19)	C6A—C7A	1.392 (4)
C4—C5	1.378 (2)	C6A—H6A	0.9300
C4—H4	0.9300	C7A—C8A	1.384 (4)
C5—N1	1.329 (2)	C7A—H7A	0.9300
C5—H5	0.9300	C8A—C9A	1.375 (3)
C6—O1	1.2312 (17)	C8A—H8A	0.9300
C6—N2	1.3376 (19)	C9A—C10A	1.477 (3)
C7—N3	1.2775 (19)	C10A—O4A	1.211 (2)
C7—C8	1.456 (2)	C10A—N1A	1.386 (2)
C7—H7	0.9300	O2A—H1OA	1.00 (3)
C8—C13	1.388 (2)	C1B—O1B	1.197 (2)
C8—C9	1.392 (2)	C1B—O2B	1.3123 (19)
C9—C10	1.368 (2)	C1B—C2B	1.517 (2)
C9—H9	0.9300	C2B—N1B	1.445 (2)
C10—C11	1.390 (2)	C2B—H2B1	0.9700
C10—H10	0.9300	C2B—H2B2	0.9700
C11—O2	1.3619 (18)	C3B—O3B	1.2036 (18)
C11—C12	1.381 (2)	C3B—N1B	1.4038 (18)
C12—C13	1.389 (2)	C3B—C4B	1.480 (2)
C12—H12	0.9300	C4B—C5B	1.378 (2)
C13—H13	0.9300	C4B—C9B	1.394 (2)
C14—O2	1.425 (2)	C5B—C6B	1.381 (2)
C14—H14A	0.9600	C5B—H5B	0.9300
C14—H14B	0.9600	C6B—C7B	1.391 (3)
C14—H14C	0.9600	C6B—H6B	0.9300
N2—N3	1.3811 (16)	C7B—C8B	1.388 (2)
N2—H1N2	0.87 (2)	C7B—H7B	0.9300
C1A—O1A	1.180 (2)	C8B—C9B	1.375 (2)
C1A—O2A	1.284 (2)	C8B—H8B	0.9300
C1A—C2A	1.516 (2)	C9B—C10B	1.484 (2)
C2A—N1A	1.446 (2)	C10B—O4B	1.2114 (18)
C2A—H2A1	0.9700	C10B—N1B	1.386 (2)
C2A—H2A2	0.9700	O2B—H1OB	0.93 (2)
C3A—O3A	1.2090 (19)
N1—C1—C2	122.73 (15)	C5A—C4A—C9A	122.03 (18)
N1—C1—H1	118.6	C5A—C4A—C3A	130.83 (17)
C2—C1—H1	118.6	C9A—C4A—C3A	107.11 (16)
C1—C2—C3	119.45 (15)	C4A—C5A—C6A	117.2 (2)
C1—C2—H2	120.3	C4A—C5A—H5A	121.4
C3—C2—H2	120.3	C6A—C5A—H5A	121.4
C4—C3—C2	117.70 (14)	C5A—C6A—C7A	120.7 (2)
C4—C3—C6	124.47 (13)	C5A—C6A—H6A	119.7
C2—C3—C6	117.81 (13)	C7A—C6A—H6A	119.7
C5—C4—C3	119.02 (14)	C8A—C7A—C6A	121.9 (2)
C5—C4—H4	120.5	C8A—C7A—H7A	119.1
C3—C4—H4	120.5	C6A—C7A—H7A	119.1
N1—C5—C4	123.38 (15)	C9A—C8A—C7A	117.3 (2)
N1—C5—H5	118.3	C9A—C8A—H8A	121.4
C4—C5—H5	118.3	C7A—C8A—H8A	121.4
O1—C6—N2	123.53 (13)	C8A—C9A—C4A	121.0 (2)
O1—C6—C3	119.79 (13)	C8A—C9A—C10A	130.3 (2)
N2—C6—C3	116.68 (12)	C4A—C9A—C10A	108.63 (16)
N3—C7—C8	120.32 (13)	O4A—C10A—N1A	124.2 (2)
N3—C7—H7	119.8	O4A—C10A—C9A	129.96 (19)
C8—C7—H7	119.8	N1A—C10A—C9A	105.85 (15)
C13—C8—C9	118.05 (14)	C10A—N1A—C3A	112.07 (15)
C13—C8—C7	121.51 (14)	C10A—N1A—C2A	122.47 (15)
C9—C8—C7	120.44 (13)	C3A—N1A—C2A	124.74 (14)
C10—C9—C8	121.12 (14)	C1A—O2A—H1OA	112.8 (14)
C10—C9—H9	119.4	O1B—C1B—O2B	125.65 (15)
C8—C9—H9	119.4	O1B—C1B—C2B	123.35 (15)
C9—C10—C11	120.42 (15)	O2B—C1B—C2B	110.99 (14)
C9—C10—H10	119.8	N1B—C2B—C1B	111.00 (13)
C11—C10—H10	119.8	N1B—C2B—H2B1	109.4
O2—C11—C12	125.81 (14)	C1B—C2B—H2B1	109.4
O2—C11—C10	114.62 (14)	N1B—C2B—H2B2	109.4
C12—C11—C10	119.54 (14)	C1B—C2B—H2B2	109.4
C11—C12—C13	119.55 (14)	H2B1—C2B—H2B2	108.0
C11—C12—H12	120.2	O3B—C3B—N1B	124.21 (15)
C13—C12—H12	120.2	O3B—C3B—C4B	130.12 (14)
C8—C13—C12	121.27 (14)	N1B—C3B—C4B	105.68 (12)
C8—C13—H13	119.4	C5B—C4B—C9B	121.58 (15)
C12—C13—H13	119.4	C5B—C4B—C3B	130.30 (14)
O2—C14—H14A	109.5	C9B—C4B—C3B	108.11 (13)
O2—C14—H14B	109.5	C4B—C5B—C6B	117.23 (15)
H14A—C14—H14B	109.5	C4B—C5B—H5B	121.4
O2—C14—H14C	109.5	C6B—C5B—H5B	121.4
H14A—C14—H14C	109.5	C5B—C6B—C7B	121.48 (16)
H14B—C14—H14C	109.5	C5B—C6B—H6B	119.3
C5—N1—C1	117.72 (14)	C7B—C6B—H6B	119.3
C6—N2—N3	118.70 (12)	C8B—C7B—C6B	121.01 (16)
C6—N2—H1N2	121.2 (13)	C8B—C7B—H7B	119.5
N3—N2—H1N2	119.8 (12)	C6B—C7B—H7B	119.5
C7—N3—N2	116.20 (12)	C9B—C8B—C7B	117.49 (15)
C11—O2—C14	117.57 (14)	C9B—C8B—H8B	121.3
O1A—C1A—O2A	124.36 (17)	C7B—C8B—H8B	121.3
O1A—C1A—C2A	120.76 (17)	C8B—C9B—C4B	121.20 (15)
O2A—C1A—C2A	114.78 (15)	C8B—C9B—C10B	130.71 (14)
N1A—C2A—C1A	113.27 (14)	C4B—C9B—C10B	108.08 (13)
N1A—C2A—H2A1	108.9	O4B—C10B—N1B	124.78 (15)
C1A—C2A—H2A1	108.9	O4B—C10B—C9B	129.25 (15)
N1A—C2A—H2A2	108.9	N1B—C10B—C9B	105.98 (12)
C1A—C2A—H2A2	108.9	C10B—N1B—C3B	112.14 (13)
H2A1—C2A—H2A2	107.7	C10B—N1B—C2B	123.63 (13)
O3A—C3A—N1A	124.53 (16)	C3B—N1B—C2B	123.10 (13)
O3A—C3A—C4A	129.13 (16)	C1B—O2B—H1OB	112.4 (14)
N1A—C3A—C4A	106.33 (14)
N1—C1—C2—C3	0.0 (3)	C3A—C4A—C9A—C10A	0.63 (18)
C1—C2—C3—C4	0.4 (2)	C8A—C9A—C10A—O4A	−2.3 (3)
C1—C2—C3—C6	−178.24 (15)	C4A—C9A—C10A—O4A	179.28 (18)
C2—C3—C4—C5	−0.5 (2)	C8A—C9A—C10A—N1A	178.19 (19)
C6—C3—C4—C5	178.00 (15)	C4A—C9A—C10A—N1A	−0.28 (18)
C3—C4—C5—N1	0.3 (3)	O4A—C10A—N1A—C3A	−179.81 (16)
C4—C3—C6—O1	−167.66 (15)	C9A—C10A—N1A—C3A	−0.21 (18)
C2—C3—C6—O1	10.8 (2)	O4A—C10A—N1A—C2A	9.5 (3)
C4—C3—C6—N2	11.7 (2)	C9A—C10A—N1A—C2A	−170.92 (14)
C2—C3—C6—N2	−169.80 (14)	O3A—C3A—N1A—C10A	−179.69 (16)
N3—C7—C8—C13	170.94 (14)	C4A—C3A—N1A—C10A	0.59 (17)
N3—C7—C8—C9	−9.4 (2)	O3A—C3A—N1A—C2A	−9.2 (3)
C13—C8—C9—C10	0.1 (3)	C4A—C3A—N1A—C2A	171.05 (14)
C7—C8—C9—C10	−179.63 (16)	C1A—C2A—N1A—C10A	80.2 (2)
C8—C9—C10—C11	−1.8 (3)	C1A—C2A—N1A—C3A	−89.3 (2)
C9—C10—C11—O2	179.91 (16)	O1B—C1B—C2B—N1B	1.4 (2)
C9—C10—C11—C12	1.8 (3)	O2B—C1B—C2B—N1B	−179.70 (12)
O2—C11—C12—C13	−178.07 (16)	O3B—C3B—C4B—C5B	−2.0 (3)
C10—C11—C12—C13	−0.2 (3)	N1B—C3B—C4B—C5B	178.67 (15)
C9—C8—C13—C12	1.5 (2)	O3B—C3B—C4B—C9B	179.29 (16)
C7—C8—C13—C12	−178.76 (15)	N1B—C3B—C4B—C9B	−0.02 (16)
C11—C12—C13—C8	−1.5 (3)	C9B—C4B—C5B—C6B	−0.4 (2)
C4—C5—N1—C1	0.0 (3)	C3B—C4B—C5B—C6B	−178.94 (15)
C2—C1—N1—C5	−0.1 (3)	C4B—C5B—C6B—C7B	−0.4 (2)
O1—C6—N2—N3	−1.0 (2)	C5B—C6B—C7B—C8B	0.5 (3)
C3—C6—N2—N3	179.68 (12)	C6B—C7B—C8B—C9B	0.1 (2)
C8—C7—N3—N2	179.59 (13)	C7B—C8B—C9B—C4B	−0.9 (2)
C6—N2—N3—C7	−179.03 (13)	C7B—C8B—C9B—C10B	177.81 (15)
C12—C11—O2—C14	−8.0 (3)	C5B—C4B—C9B—C8B	1.0 (2)
C10—C11—O2—C14	174.13 (16)	C3B—C4B—C9B—C8B	179.88 (13)
O1A—C1A—C2A—N1A	−161.2 (2)	C5B—C4B—C9B—C10B	−177.90 (13)
O2A—C1A—C2A—N1A	22.3 (2)	C3B—C4B—C9B—C10B	0.93 (16)
O3A—C3A—C4A—C5A	1.4 (3)	C8B—C9B—C10B—O4B	−0.1 (3)
N1A—C3A—C4A—C5A	−178.94 (17)	C4B—C9B—C10B—O4B	178.70 (15)
O3A—C3A—C4A—C9A	179.55 (17)	C8B—C9B—C10B—N1B	179.68 (15)
N1A—C3A—C4A—C9A	−0.75 (17)	C4B—C9B—C10B—N1B	−1.50 (16)
C9A—C4A—C5A—C6A	−0.7 (3)	O4B—C10B—N1B—C3B	−178.65 (14)
C3A—C4A—C5A—C6A	177.28 (17)	C9B—C10B—N1B—C3B	1.54 (16)
C4A—C5A—C6A—C7A	0.5 (3)	O4B—C10B—N1B—C2B	−10.5 (2)
C5A—C6A—C7A—C8A	0.0 (3)	C9B—C10B—N1B—C2B	169.65 (13)
C6A—C7A—C8A—C9A	−0.3 (3)	O3B—C3B—N1B—C10B	179.65 (14)
C7A—C8A—C9A—C4A	0.1 (3)	C4B—C3B—N1B—C10B	−0.99 (16)
C7A—C8A—C9A—C10A	−178.19 (19)	O3B—C3B—N1B—C2B	11.5 (2)
C5A—C4A—C9A—C8A	0.4 (3)	C4B—C3B—N1B—C2B	−169.17 (13)
C3A—C4A—C9A—C8A	−178.01 (17)	C1B—C2B—N1B—C10B	−71.42 (18)
C5A—C4A—C9A—C10A	179.01 (15)	C1B—C2B—N1B—C3B	95.41 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O2A—H1OA···N1	1.00 (3)	1.60 (3)	2.5997 (19)	177 (2)
O2B—H1OB···O1	0.93 (2)	1.75 (2)	2.6736 (16)	170 (2)
N2—H1N2···O4Bi	0.87 (2)	2.22 (2)	3.0549 (18)	161 (2)
C2A—H2A2···O3Bii	0.97	2.57	3.477 (2)	156
C5B—H5B···O1iii	0.93	2.51	3.158 (2)	126
C7B—H7B···O3Biv	0.93	2.55	3.275 (2)	135
C5—H5···O3Av	0.93	2.48	3.341 (2)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2A—H1OA⋯N1	1.00 (3)	1.60 (3)	2.5997 (19)	177 (2)
O2B—H1OB⋯O1	0.93 (2)	1.75 (2)	2.6736 (16)	170 (2)
N2—H1N2⋯O4B i	0.87 (2)	2.22 (2)	3.0549 (18)	161 (2)
C2A—H2A2⋯O3B ii	0.97	2.57	3.477 (2)	156
C5B—H5B⋯O1iii	0.93	2.51	3.158 (2)	126
C7B—H7B⋯O3B iv	0.93	2.55	3.275 (2)	135
C5—H5⋯O3A v	0.93	2.48	3.341 (2)	154

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .