Crystal structure of a second triclinic polymorph of 2-methyl-pyridinium picrate.

The title mol-ecular salt, C6H8N(+)·C6H2N3O7 (-) (systematic name: 2-methyl-pyridinium 2,4,6-tri-nitro-phenolate), crystallizes with two cations and two anions in the asymmetric unit. In the crystal, the cations are linked to the anions via bifurcated N-H⋯(O,O) hydrogen bonds, generating R 1 (2)(6) graph-set motifs. Numerous C-H⋯O hydrogen bonds are observed between these cation-anion pairs, which result in a three-dimensional network. In addition, weak aromatic π-π stacking between the 2-methyl-pyridinium rings [inter-centroid distance = 3.8334 (19) Å] and very weak stacking [inter-centroid distance = 4.0281 (16) Å] between inversion-related pairs of picrate anions is observed. The title salt is a second triclinic polymorph of the structure (also with Z' = 2) reported earlier [Anita et al. (2006). Acta Cryst. C62, o567-o570; Chan et al. (2014 ▸). CrystEngComm, 16, 4508-4538]. In the title compound, the cations and anions display a chequerboard arrangement when viewed down [100], whereas in the first polymorph, (010) layers of alternating cations and anions are apparent in a [100] view. It is inter-esting that the unit-cell lengths are almost identical for the two polymorphs, although the inter-axial angles are quite different.

Related literature

For the first triclinic polymorph of 2-methyl­pyridinium picrate, see: Anitha et al. (2006 ▸); Chan et al. (2014 ▸). For the crystal structure of the isomeric 3-methyl­pyridinium picrate, see: Gomathi & Kalaivani (2015 ▸).

Experimental

Crystal data

C6H8N+·C6H2N3O7 −

M = 322.24

Triclinic,

a = 8.1524 (4) Å

b = 11.8809 (6) Å

c = 14.6377 (9) Å

α = 102.077 (3)°

β = 90.001 (3)°

γ = 100.692 (3)°

V = 1361.21 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 296 K

0.35 × 0.35 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▸) T min = 0.952, T max = 0.969

25854 measured reflections

4789 independent reflections

3165 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.159

S = 1.06

4789 reflections

423 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: SAINT (Bruker, 2004 ▸); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: SHELXL2014.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S205698901501912X/hb7512sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901501912X/hb7512Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S205698901501912X/hb7512Isup3.cml

Click here for additional data file.

ORTEP . DOI: 10.1107/S205698901501912X/hb7512fig1.tif

ORTEP view of the title mol­ecular salt with displacement ellipsoids drawn at 40% probability.

Click here for additional data file.

. DOI: 10.1107/S205698901501912X/hb7512fig2.tif

A partial view of the crystal packing diagram of the title mol­ecular salt (hydrogen bonds and π–π stacking are shown as dotted lines).

CCDC reference: 1417625

Additional supporting information: crystallographic information; 3D view; checkCIF report

C6H8N+·C6H2N3O7−	Z = 4
Mr = 322.24	F(000) = 664
Triclinic, P1	Dx = 1.572 Mg m−3
a = 8.1524 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.8809 (6) Å	Cell parameters from 6819 reflections
c = 14.6377 (9) Å	θ = 2.5–25.5°
α = 102.077 (3)°	µ = 0.13 mm−1
β = 90.001 (3)°	T = 296 K
γ = 100.692 (3)°	Block, yellow
V = 1361.21 (13) Å3	0.35 × 0.35 × 0.30 mm

Bruker Kappa APEXII CCD diffractometer	4789 independent reflections
Radiation source: fine-focus sealed tube	3165 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω and φ scan	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→9
Tmin = 0.952, Tmax = 0.969	k = −14→14
25854 measured reflections	l = −17→17

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.159	w = 1/[σ2(Fo2) + (0.0576P)2 + 1.224P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
4789 reflections	Δρmax = 0.35 e Å−3
423 parameters	Δρmin = −0.27 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.2716 (3)	0.1874 (2)	0.86637 (19)	0.0366 (6)
C2	0.2025 (3)	0.2910 (2)	0.8744 (2)	0.0393 (7)
C3	0.2970 (3)	0.4009 (2)	0.8818 (2)	0.0411 (7)
H3	0.2457	0.4657	0.8877	0.049*
C4	0.4672 (3)	0.4148 (2)	0.88062 (19)	0.0369 (6)
C5	0.5471 (3)	0.3206 (2)	0.87618 (19)	0.0359 (6)
H5	0.6630	0.3308	0.8777	0.043*
C6	0.4504 (3)	0.2134 (2)	0.86961 (19)	0.0345 (6)
C7	0.6949 (3)	0.3848 (2)	0.64217 (19)	0.0367 (6)
C8	0.5153 (3)	0.3557 (2)	0.62748 (19)	0.0359 (6)
C9	0.4225 (3)	0.2467 (2)	0.61397 (19)	0.0372 (6)
H9	0.3071	0.2346	0.6047	0.045*
C10	0.5014 (3)	0.1533 (2)	0.61406 (19)	0.0361 (6)
C11	0.6715 (3)	0.1706 (2)	0.62624 (19)	0.0382 (7)
H11	0.7239	0.1071	0.6248	0.046*
C12	0.7637 (3)	0.2815 (2)	0.64042 (19)	0.0370 (6)
C13	1.1475 (4)	0.6975 (3)	0.6877 (2)	0.0460 (7)
C14	1.2631 (4)	0.7880 (3)	0.7391 (3)	0.0559 (9)
H14	1.3302	0.8401	0.7090	0.067*
C15	1.2802 (4)	0.8019 (3)	0.8328 (3)	0.0592 (9)
H15	1.3584	0.8635	0.8667	0.071*
C16	1.1837 (4)	0.7263 (3)	0.8779 (3)	0.0572 (9)
H16	1.1961	0.7346	0.9422	0.069*
C17	1.0688 (4)	0.6385 (3)	0.8267 (3)	0.0535 (8)
H17	1.0012	0.5860	0.8562	0.064*
C18	1.1222 (5)	0.6719 (4)	0.5849 (3)	0.0747 (11)
H18A	1.1979	0.7286	0.5597	0.112*
H18B	1.1430	0.5948	0.5592	0.112*
H18C	1.0093	0.6755	0.5691	0.112*
C19	−0.1835 (3)	−0.1337 (2)	0.8099 (2)	0.0412 (7)
C20	−0.2865 (4)	−0.2209 (3)	0.7485 (2)	0.0524 (8)
H20	−0.3591	−0.2782	0.7708	0.063*
C21	−0.2835 (4)	−0.2242 (3)	0.6552 (3)	0.0627 (10)
H21	−0.3535	−0.2839	0.6138	0.075*
C22	−0.1775 (5)	−0.1400 (3)	0.6221 (3)	0.0640 (10)
H22	−0.1753	−0.1408	0.5584	0.077*
C23	−0.0760 (4)	−0.0555 (3)	0.6837 (3)	0.0569 (9)
H23	−0.0024	0.0022	0.6623	0.068*
C24	−0.1811 (5)	−0.1215 (3)	0.9123 (2)	0.0641 (9)
H24A	−0.2608	−0.1842	0.9281	0.096*
H24B	−0.0715	−0.1247	0.9343	0.096*
H24C	−0.2096	−0.0477	0.9412	0.096*
N1	0.0244 (3)	0.2838 (3)	0.8789 (2)	0.0583 (8)
N2	0.5652 (3)	0.5307 (2)	0.88834 (18)	0.0459 (6)
N3	0.5319 (3)	0.1137 (2)	0.86915 (19)	0.0420 (6)
N4	0.9426 (3)	0.2915 (2)	0.6504 (2)	0.0513 (7)
N5	0.4056 (3)	0.0360 (2)	0.59800 (18)	0.0463 (6)
N6	0.4285 (3)	0.4513 (2)	0.6237 (2)	0.0485 (7)
N7	1.0518 (3)	0.6267 (2)	0.7348 (2)	0.0458 (6)
N8	−0.0805 (3)	−0.0542 (2)	0.7744 (2)	0.0455 (6)
O1	−0.0686 (3)	0.1928 (2)	0.8495 (3)	0.1149 (13)
O2	−0.0287 (3)	0.3707 (2)	0.9134 (3)	0.0944 (10)
O3	0.7155 (3)	0.5408 (2)	0.8829 (2)	0.0747 (8)
O4	0.4947 (3)	0.61454 (18)	0.90051 (17)	0.0594 (6)
O5	0.5817 (4)	0.1009 (3)	0.9423 (2)	0.0988 (11)
O6	0.5417 (4)	0.0464 (2)	0.79711 (19)	0.0767 (8)
O7	0.1934 (2)	0.08461 (17)	0.86122 (15)	0.0512 (6)
O8	1.0032 (3)	0.2064 (2)	0.6182 (2)	0.0866 (9)
O9	1.0276 (3)	0.3819 (2)	0.6908 (2)	0.0953 (10)
O10	0.4784 (3)	−0.04584 (18)	0.59417 (15)	0.0536 (6)
O11	0.2538 (3)	0.0224 (2)	0.5862 (2)	0.0737 (8)
O12	0.3364 (4)	0.4393 (3)	0.5559 (2)	0.0983 (11)
O13	0.4468 (3)	0.5344 (2)	0.6878 (2)	0.0752 (8)
O14	0.7744 (2)	0.48653 (17)	0.64961 (16)	0.0523 (6)
H7A	0.970 (5)	0.565 (3)	0.700 (2)	0.072 (11)*
H8A	−0.003 (5)	0.005 (3)	0.814 (3)	0.085 (12)*

	U11	U22	U33	U12	U13	U23
C1	0.0308 (14)	0.0384 (16)	0.0384 (16)	−0.0002 (12)	−0.0031 (11)	0.0091 (13)
C2	0.0229 (13)	0.0440 (17)	0.0499 (18)	0.0025 (12)	−0.0006 (11)	0.0104 (14)
C3	0.0349 (15)	0.0379 (16)	0.0528 (19)	0.0088 (12)	0.0022 (13)	0.0132 (14)
C4	0.0305 (14)	0.0343 (15)	0.0437 (17)	−0.0009 (11)	0.0022 (12)	0.0098 (13)
C5	0.0269 (13)	0.0381 (15)	0.0403 (16)	0.0011 (11)	0.0017 (11)	0.0074 (12)
C6	0.0314 (14)	0.0352 (15)	0.0366 (16)	0.0059 (11)	−0.0018 (11)	0.0071 (12)
C7	0.0318 (14)	0.0365 (16)	0.0390 (16)	0.0017 (12)	−0.0023 (11)	0.0063 (13)
C8	0.0317 (14)	0.0326 (15)	0.0423 (17)	0.0067 (11)	−0.0019 (11)	0.0052 (12)
C9	0.0268 (13)	0.0414 (16)	0.0409 (17)	0.0048 (12)	0.0012 (11)	0.0046 (13)
C10	0.0329 (14)	0.0318 (15)	0.0411 (17)	0.0019 (11)	0.0042 (11)	0.0057 (12)
C11	0.0361 (15)	0.0349 (15)	0.0450 (17)	0.0097 (12)	0.0056 (12)	0.0094 (13)
C12	0.0274 (13)	0.0402 (16)	0.0428 (17)	0.0048 (12)	−0.0006 (11)	0.0086 (13)
C13	0.0430 (16)	0.0397 (17)	0.060 (2)	0.0148 (14)	0.0040 (14)	0.0156 (15)
C14	0.0464 (18)	0.0427 (18)	0.079 (3)	−0.0026 (14)	0.0071 (17)	0.0229 (17)
C15	0.053 (2)	0.0429 (19)	0.074 (3)	−0.0037 (15)	−0.0136 (17)	0.0069 (17)
C16	0.0511 (19)	0.063 (2)	0.057 (2)	0.0121 (17)	−0.0037 (16)	0.0115 (18)
C17	0.0365 (16)	0.056 (2)	0.072 (3)	0.0031 (14)	0.0095 (15)	0.0270 (18)
C18	0.098 (3)	0.076 (3)	0.057 (2)	0.035 (2)	0.006 (2)	0.014 (2)
C19	0.0365 (15)	0.0333 (15)	0.0545 (19)	0.0067 (12)	0.0012 (13)	0.0106 (14)
C20	0.0489 (18)	0.0364 (17)	0.067 (2)	−0.0052 (14)	−0.0052 (16)	0.0111 (16)
C21	0.063 (2)	0.048 (2)	0.069 (3)	0.0044 (17)	−0.0196 (18)	−0.0004 (18)
C22	0.071 (2)	0.074 (3)	0.050 (2)	0.022 (2)	−0.0042 (18)	0.0120 (19)
C23	0.0455 (18)	0.062 (2)	0.071 (3)	0.0114 (16)	0.0139 (17)	0.0315 (19)
C24	0.073 (2)	0.063 (2)	0.055 (2)	0.0104 (18)	0.0016 (17)	0.0122 (18)
N1	0.0306 (14)	0.0527 (17)	0.091 (2)	0.0057 (13)	0.0026 (13)	0.0164 (16)
N2	0.0393 (14)	0.0389 (15)	0.0577 (17)	−0.0015 (11)	0.0034 (11)	0.0140 (12)
N3	0.0369 (13)	0.0374 (14)	0.0507 (17)	0.0042 (10)	−0.0032 (11)	0.0095 (13)
N4	0.0319 (13)	0.0450 (16)	0.078 (2)	0.0065 (12)	−0.0019 (12)	0.0159 (14)
N5	0.0416 (15)	0.0393 (15)	0.0535 (16)	−0.0004 (12)	0.0106 (11)	0.0073 (12)
N6	0.0413 (14)	0.0418 (15)	0.0621 (18)	0.0093 (11)	−0.0072 (13)	0.0090 (14)
N7	0.0325 (13)	0.0381 (14)	0.0644 (19)	0.0009 (11)	−0.0052 (12)	0.0107 (13)
N8	0.0334 (13)	0.0389 (14)	0.0624 (19)	0.0024 (11)	−0.0012 (12)	0.0103 (13)
O1	0.0293 (13)	0.0564 (17)	0.239 (4)	−0.0057 (12)	−0.0048 (17)	−0.003 (2)
O2	0.0400 (14)	0.0627 (17)	0.181 (3)	0.0171 (12)	0.0187 (16)	0.0202 (19)
O3	0.0350 (13)	0.0545 (15)	0.131 (2)	−0.0054 (10)	0.0125 (13)	0.0251 (15)
O4	0.0605 (14)	0.0346 (12)	0.0830 (17)	0.0070 (10)	0.0091 (12)	0.0143 (11)
O5	0.151 (3)	0.096 (2)	0.0671 (19)	0.072 (2)	−0.0282 (18)	0.0147 (16)
O6	0.108 (2)	0.0571 (16)	0.0671 (18)	0.0379 (15)	0.0000 (15)	−0.0016 (14)
O7	0.0380 (11)	0.0385 (12)	0.0740 (15)	−0.0062 (9)	−0.0104 (10)	0.0170 (10)
O8	0.0375 (13)	0.0568 (16)	0.165 (3)	0.0165 (12)	0.0103 (15)	0.0163 (17)
O9	0.0410 (14)	0.0557 (16)	0.176 (3)	0.0013 (12)	−0.0321 (16)	0.0013 (18)
O10	0.0617 (14)	0.0335 (12)	0.0650 (15)	0.0068 (10)	0.0075 (11)	0.0113 (10)
O11	0.0383 (13)	0.0528 (14)	0.120 (2)	−0.0063 (10)	0.0119 (13)	0.0102 (14)
O12	0.122 (2)	0.091 (2)	0.089 (2)	0.0606 (19)	−0.0448 (19)	0.0001 (16)
O13	0.0726 (17)	0.0431 (14)	0.101 (2)	0.0219 (12)	−0.0229 (14)	−0.0149 (14)
O14	0.0399 (11)	0.0373 (12)	0.0764 (16)	−0.0041 (9)	−0.0136 (10)	0.0151 (11)

C1—O7	1.256 (3)	C17—N7	1.328 (4)
C1—C2	1.429 (4)	C17—H17	0.9300
C1—C6	1.431 (4)	C18—H18A	0.9600
C2—C3	1.371 (4)	C18—H18B	0.9600
C2—N1	1.441 (3)	C18—H18C	0.9600
C3—C4	1.367 (4)	C19—N8	1.334 (4)
C3—H3	0.9300	C19—C20	1.369 (4)
C4—C5	1.385 (4)	C19—C24	1.475 (4)
C4—N2	1.441 (3)	C20—C21	1.358 (5)
C5—C6	1.353 (4)	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.366 (5)
C6—N3	1.459 (3)	C21—H21	0.9300
C7—O14	1.244 (3)	C22—C23	1.348 (5)
C7—C12	1.437 (4)	C22—H22	0.9300
C7—C8	1.446 (4)	C23—N8	1.325 (4)
C8—C9	1.348 (4)	C23—H23	0.9300
C8—N6	1.455 (4)	C24—H24A	0.9600
C9—C10	1.382 (4)	C24—H24B	0.9600
C9—H9	0.9300	C24—H24C	0.9600
C10—C11	1.370 (4)	N1—O1	1.196 (3)
C10—N5	1.438 (3)	N1—O2	1.206 (3)
C11—C12	1.365 (4)	N2—O3	1.213 (3)
C11—H11	0.9300	N2—O4	1.222 (3)
C12—N4	1.446 (3)	N3—O5	1.193 (3)
C13—N7	1.337 (4)	N3—O6	1.195 (3)
C13—C14	1.377 (4)	N4—O9	1.200 (3)
C13—C18	1.478 (5)	N4—O8	1.215 (3)
C14—C15	1.351 (5)	N5—O10	1.222 (3)
C14—H14	0.9300	N5—O11	1.225 (3)
C15—C16	1.358 (5)	N6—O13	1.198 (3)
C15—H15	0.9300	N6—O12	1.213 (3)
C16—C17	1.356 (5)	N7—H7A	0.95 (4)
C16—H16	0.9300	N8—H8A	0.94 (4)
O7—C1—C2	127.2 (2)	C13—C18—H18A	109.5
O7—C1—C6	121.0 (3)	C13—C18—H18B	109.5
C2—C1—C6	111.7 (2)	H18A—C18—H18B	109.5
C3—C2—C1	123.7 (2)	C13—C18—H18C	109.5
C3—C2—N1	116.3 (3)	H18A—C18—H18C	109.5
C1—C2—N1	120.0 (2)	H18B—C18—H18C	109.5
C4—C3—C2	119.5 (3)	N8—C19—C20	117.5 (3)
C4—C3—H3	120.2	N8—C19—C24	118.3 (3)
C2—C3—H3	120.2	C20—C19—C24	124.2 (3)
C3—C4—C5	121.4 (2)	C21—C20—C19	120.5 (3)
C3—C4—N2	119.0 (2)	C21—C20—H20	119.8
C5—C4—N2	119.5 (2)	C19—C20—H20	119.8
C6—C5—C4	117.6 (2)	C20—C21—C22	120.0 (3)
C6—C5—H5	121.2	C20—C21—H21	120.0
C4—C5—H5	121.2	C22—C21—H21	120.0
C5—C6—C1	126.0 (3)	C23—C22—C21	118.6 (3)
C5—C6—N3	118.6 (2)	C23—C22—H22	120.7
C1—C6—N3	115.4 (2)	C21—C22—H22	120.7
O14—C7—C12	126.6 (2)	N8—C23—C22	120.4 (3)
O14—C7—C8	122.2 (2)	N8—C23—H23	119.8
C12—C7—C8	111.0 (2)	C22—C23—H23	119.8
C9—C8—C7	125.3 (2)	C19—C24—H24A	109.5
C9—C8—N6	117.4 (2)	C19—C24—H24B	109.5
C7—C8—N6	117.3 (2)	H24A—C24—H24B	109.5
C8—C9—C10	119.0 (2)	C19—C24—H24C	109.5
C8—C9—H9	120.5	H24A—C24—H24C	109.5
C10—C9—H9	120.5	H24B—C24—H24C	109.5
C11—C10—C9	120.7 (2)	O1—N1—O2	120.9 (3)
C11—C10—N5	119.2 (2)	O1—N1—C2	120.3 (3)
C9—C10—N5	120.1 (2)	O2—N1—C2	118.9 (3)
C12—C11—C10	119.6 (3)	O3—N2—O4	122.7 (2)
C12—C11—H11	120.2	O3—N2—C4	118.2 (2)
C10—C11—H11	120.2	O4—N2—C4	119.1 (2)
C11—C12—C7	124.4 (2)	O5—N3—O6	122.5 (3)
C11—C12—N4	116.0 (2)	O5—N3—C6	117.9 (3)
C7—C12—N4	119.6 (2)	O6—N3—C6	119.6 (3)
N7—C13—C14	117.2 (3)	O9—N4—O8	121.5 (3)
N7—C13—C18	117.6 (3)	O9—N4—C12	120.1 (3)
C14—C13—C18	125.2 (3)	O8—N4—C12	118.4 (3)
C15—C14—C13	120.7 (3)	O10—N5—O11	122.8 (2)
C15—C14—H14	119.7	O10—N5—C10	119.1 (2)
C13—C14—H14	119.7	O11—N5—C10	118.1 (2)
C14—C15—C16	120.4 (3)	O13—N6—O12	123.8 (3)
C14—C15—H15	119.8	O13—N6—C8	119.2 (3)
C16—C15—H15	119.8	O12—N6—C8	116.9 (3)
C17—C16—C15	118.3 (3)	C17—N7—C13	122.7 (3)
C17—C16—H16	120.8	C17—N7—H7A	119 (2)
C15—C16—H16	120.8	C13—N7—H7A	118 (2)
N7—C17—C16	120.6 (3)	C23—N8—C19	123.0 (3)
N7—C17—H17	119.7	C23—N8—H8A	116 (2)
C16—C17—H17	119.7	C19—N8—H8A	121 (2)
O7—C1—C2—C3	178.5 (3)	C15—C16—C17—N7	0.2 (5)
C6—C1—C2—C3	1.6 (4)	N8—C19—C20—C21	−0.7 (5)
O7—C1—C2—N1	1.0 (5)	C24—C19—C20—C21	178.5 (3)
C6—C1—C2—N1	−175.8 (3)	C19—C20—C21—C22	−0.2 (5)
C1—C2—C3—C4	0.8 (5)	C20—C21—C22—C23	0.8 (5)
N1—C2—C3—C4	178.3 (3)	C21—C22—C23—N8	−0.5 (5)
C2—C3—C4—C5	−2.9 (4)	C3—C2—N1—O1	160.5 (4)
C2—C3—C4—N2	179.9 (3)	C1—C2—N1—O1	−21.9 (5)
C3—C4—C5—C6	2.4 (4)	C3—C2—N1—O2	−20.0 (5)
N2—C4—C5—C6	179.6 (2)	C1—C2—N1—O2	157.6 (3)
C4—C5—C6—C1	0.3 (4)	C3—C4—N2—O3	−176.7 (3)
C4—C5—C6—N3	−177.2 (2)	C5—C4—N2—O3	6.0 (4)
O7—C1—C6—C5	−179.2 (3)	C3—C4—N2—O4	3.7 (4)
C2—C1—C6—C5	−2.1 (4)	C5—C4—N2—O4	−173.6 (3)
O7—C1—C6—N3	−1.6 (4)	C5—C6—N3—O5	79.3 (4)
C2—C1—C6—N3	175.5 (2)	C1—C6—N3—O5	−98.5 (3)
O14—C7—C8—C9	176.3 (3)	C5—C6—N3—O6	−103.1 (3)
C12—C7—C8—C9	0.1 (4)	C1—C6—N3—O6	79.1 (3)
O14—C7—C8—N6	−1.4 (4)	C11—C12—N4—O9	−156.7 (3)
C12—C7—C8—N6	−177.6 (2)	C7—C12—N4—O9	25.7 (4)
C7—C8—C9—C10	0.2 (4)	C11—C12—N4—O8	22.4 (4)
N6—C8—C9—C10	177.9 (3)	C7—C12—N4—O8	−155.2 (3)
C8—C9—C10—C11	−1.0 (4)	C11—C10—N5—O10	−1.1 (4)
C8—C9—C10—N5	−178.8 (3)	C9—C10—N5—O10	176.7 (3)
C9—C10—C11—C12	1.4 (4)	C11—C10—N5—O11	−179.2 (3)
N5—C10—C11—C12	179.2 (2)	C9—C10—N5—O11	−1.4 (4)
C10—C11—C12—C7	−1.1 (4)	C9—C8—N6—O13	126.6 (3)
C10—C11—C12—N4	−178.6 (3)	C7—C8—N6—O13	−55.5 (4)
O14—C7—C12—C11	−175.7 (3)	C9—C8—N6—O12	−51.1 (4)
C8—C7—C12—C11	0.3 (4)	C7—C8—N6—O12	126.8 (3)
O14—C7—C12—N4	1.7 (4)	C16—C17—N7—C13	1.6 (5)
C8—C7—C12—N4	177.8 (2)	C14—C13—N7—C17	−2.4 (4)
N7—C13—C14—C15	1.4 (5)	C18—C13—N7—C17	177.0 (3)
C18—C13—C14—C15	−177.9 (3)	C22—C23—N8—C19	−0.4 (5)
C13—C14—C15—C16	0.2 (5)	C20—C19—N8—C23	1.0 (4)
C14—C15—C16—C17	−1.1 (5)	C24—C19—N8—C23	−178.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7A···O9	0.95 (4)	2.28 (4)	2.813 (4)	114 (3)
N7—H7A···O14	0.95 (4)	1.76 (4)	2.678 (3)	160 (3)
N8—H8A···O1	0.94 (4)	2.35 (4)	2.894 (4)	117 (3)
N8—H8A···O7	0.94 (4)	1.76 (4)	2.660 (3)	158 (4)
C5—H5···O2i	0.93	2.50	3.423 (4)	170
C9—H9···O8ii	0.93	2.45	3.365 (3)	167
C14—H14···O10iii	0.93	2.54	3.456 (4)	167
C17—H17···O3	0.93	2.34	3.078 (4)	136
C18—H18B···O12i	0.96	2.64	3.488 (5)	148
C20—H20···O13iv	0.93	2.55	3.247 (4)	132
C23—H23···O8ii	0.93	2.63	3.394 (4)	140
C23—H23···O11	0.93	2.36	3.122 (4)	139

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N7H7AO9	0.95(4)	2.28(4)	2.813(4)	114(3)
N7H7AO14	0.95(4)	1.76(4)	2.678(3)	160(3)
N8H8AO1	0.94(4)	2.35(4)	2.894(4)	117(3)
N8H8AO7	0.94(4)	1.76(4)	2.660(3)	158(4)
C5H5O2i	0.93	2.50	3.423(4)	170
C9H9O8ii	0.93	2.45	3.365(3)	167
C14H14O10iii	0.93	2.54	3.456(4)	167
C17H17O3	0.93	2.34	3.078(4)	136
C18H18BO12i	0.96	2.64	3.488(5)	148
C20H20O13iv	0.93	2.55	3.247(4)	132
C23H23O8ii	0.93	2.63	3.394(4)	140
C23H23O11	0.93	2.36	3.122(4)	139

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