2-Iodo-N-(6-methyl-2-pyrid-yl)benzamide.

The asymmetric unit of the title compound, C(13)H(11)IN(2)O, comprises two crystallographically independent mol-ecules. The dihedral angles between the ring planes are 53.56 (9) and 72.14 (19)° in the two molecules. Pairs of inter-molecular N-H⋯N hydrogen bonds and I⋯O inter-actions link neighbouring mol-ecules into two different pairs of dimers, those involving N-H⋯N interactions having R(2) (2)(8) ring motifs. Short inter-molecular I⋯O [3.1458 (15) Å] and I⋯N [3.4834 (16) Å] contacts are present. The crystal structure is further stabilized by inter-molecular C-H⋯π inter-actions [3.565 (2) and 3.629 (2) Å].

Related literature

For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For applications in supramolecular chemistry and molecular recognition, see, for example: Goswami & Dey (2006 ▶); Goswami et al. (2005 ▶); Steed & Atwood (2001 ▶); Lehn (1995 ▶); Desiraju (2003 ▶).

Experimental

Crystal data

C13H11IN2O

M = 338.14

Triclinic,

a = 9.8687 (3) Å

b = 10.1276 (3) Å

c = 13.6366 (4) Å

α = 97.521 (1)°

β = 93.113 (1)°

γ = 110.380 (1)°

V = 1259.28 (6) Å3

Z = 4

Mo Kα radiation

μ = 2.53 mm−1

T = 100.0 (1) K

0.49 × 0.32 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.374, T max = 0.746

47136 measured reflections

11804 independent reflections

9568 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.090

S = 1.05

11804 reflections

317 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 2.34 e Å−3

Δρmin = −1.51 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808041950/tk2344sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041950/tk2344Isup2.hkl

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

C13H11IN2O	Z = 4
Mr = 338.14	F(000) = 656
Triclinic, P1	Dx = 1.784 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8687 (3) Å	Cell parameters from 9385 reflections
b = 10.1276 (3) Å	θ = 2.5–35.9°
c = 13.6366 (4) Å	µ = 2.53 mm−1
α = 97.521 (1)°	T = 100 K
β = 93.113 (1)°	Plate, colourless
γ = 110.380 (1)°	0.49 × 0.32 × 0.12 mm
V = 1259.28 (6) Å3

Bruker SMART APEXII CCD area-detector diffractometer	11804 independent reflections
Radiation source: fine-focus sealed tube	9568 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 36.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −16→16
Tmin = 0.374, Tmax = 0.746	k = −16→16
47136 measured reflections	l = −22→21

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0498P)2] where P = (Fo2 + 2Fc2)/3
11804 reflections	(Δ/σ)max = 0.002
317 parameters	Δρmax = 2.34 e Å−3
0 restraints	Δρmin = −1.51 e Å−3

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
I1A	0.600768 (13)	0.719329 (12)	0.055937 (8)	0.02055 (4)
O1A	0.73426 (15)	0.40166 (14)	0.01538 (10)	0.0225 (3)
N1A	0.71156 (17)	0.46318 (15)	0.17981 (11)	0.0178 (3)
N2A	0.53614 (17)	0.34154 (15)	0.27329 (11)	0.0179 (3)
C1A	0.8221 (2)	0.75540 (18)	0.08834 (12)	0.0181 (3)
C2A	0.9243 (2)	0.89336 (19)	0.09553 (14)	0.0229 (3)
H2AA	0.8937	0.9700	0.0928	0.027*
C3A	1.0713 (2)	0.9156 (2)	0.10670 (14)	0.0246 (4)
H3AA	1.1393	1.0077	0.1128	0.030*
C4A	1.1178 (2)	0.8017 (2)	0.10882 (14)	0.0245 (4)
H4AA	1.2166	0.8169	0.1141	0.029*
C5A	1.0165 (2)	0.6648 (2)	0.10306 (14)	0.0228 (3)
H5AA	1.0479	0.5885	0.1049	0.027*
C6A	0.86799 (19)	0.64057 (17)	0.09455 (12)	0.0176 (3)
C7A	0.76383 (19)	0.49040 (17)	0.09119 (13)	0.0174 (3)
C8A	0.61757 (19)	0.32996 (17)	0.19928 (12)	0.0170 (3)
C9A	0.6157 (2)	0.20087 (18)	0.14923 (14)	0.0218 (3)
H9AA	0.6738	0.1973	0.0983	0.026*
C10A	0.5238 (2)	0.07761 (19)	0.17815 (16)	0.0260 (4)
H10A	0.5191	−0.0112	0.1464	0.031*
C11A	0.4392 (2)	0.08663 (19)	0.25418 (15)	0.0243 (4)
H11A	0.3774	0.0043	0.2741	0.029*
C12A	0.4472 (2)	0.22025 (19)	0.30064 (14)	0.0206 (3)
C13A	0.3562 (2)	0.2346 (2)	0.38233 (16)	0.0267 (4)
H13A	0.4006	0.3270	0.4226	0.040*
H13B	0.3485	0.1620	0.4227	0.040*
H13C	0.2610	0.2241	0.3543	0.040*
I1B	0.755985 (14)	0.434720 (13)	0.498669 (9)	0.02504 (4)
O1B	0.64755 (17)	0.24584 (15)	0.71745 (14)	0.0330 (4)
N1B	0.49390 (17)	0.36405 (15)	0.68719 (11)	0.0176 (3)
N2B	0.24463 (17)	0.28564 (15)	0.66686 (11)	0.0182 (3)
C1B	0.8325 (2)	0.53935 (18)	0.64543 (13)	0.0194 (3)
C2B	0.9594 (2)	0.65908 (19)	0.66103 (14)	0.0221 (3)
H2BA	1.0122	0.6876	0.6082	0.027*
C3B	1.0066 (2)	0.7357 (2)	0.75644 (14)	0.0229 (3)
H3BA	1.0923	0.8151	0.7677	0.027*
C4B	0.9267 (2)	0.6946 (2)	0.83480 (14)	0.0244 (4)
H4BA	0.9578	0.7474	0.8983	0.029*
C5B	0.7997 (2)	0.57396 (19)	0.81873 (14)	0.0217 (3)
H5BA	0.7461	0.5464	0.8714	0.026*
C6B	0.75314 (19)	0.49482 (17)	0.72370 (12)	0.0170 (3)
C7B	0.6259 (2)	0.35554 (18)	0.70882 (13)	0.0199 (3)
C8B	0.3617 (2)	0.24816 (17)	0.66336 (12)	0.0180 (3)
C9B	0.3545 (2)	0.10825 (18)	0.63597 (14)	0.0222 (3)
H9BA	0.4381	0.0859	0.6336	0.027*
C10B	0.2170 (2)	0.0036 (2)	0.61241 (15)	0.0265 (4)
H10B	0.2071	−0.0914	0.5948	0.032*
C11B	0.0950 (2)	0.0406 (2)	0.61509 (14)	0.0257 (4)
H11B	0.0027	−0.0291	0.5998	0.031*
C12B	0.1116 (2)	0.18363 (19)	0.64094 (13)	0.0214 (3)
C13B	−0.0153 (2)	0.2316 (2)	0.63969 (16)	0.0282 (4)
H13D	0.0075	0.3177	0.6866	0.042*
H13E	−0.0983	0.1587	0.6574	0.042*
H13F	−0.0367	0.2494	0.5742	0.042*
H1NA	0.728 (3)	0.530 (3)	0.2269 (19)	0.030 (7)*
H1NB	0.485 (3)	0.444 (3)	0.6892 (19)	0.035 (7)*

	U11	U22	U33	U12	U13	U23
I1A	0.02262 (6)	0.01832 (5)	0.02205 (6)	0.00989 (4)	0.00152 (4)	0.00112 (4)
O1A	0.0268 (7)	0.0187 (6)	0.0190 (6)	0.0057 (5)	0.0032 (5)	−0.0012 (5)
N1A	0.0217 (7)	0.0118 (5)	0.0179 (6)	0.0038 (5)	0.0027 (5)	0.0008 (5)
N2A	0.0194 (7)	0.0138 (6)	0.0189 (6)	0.0039 (5)	0.0009 (5)	0.0029 (5)
C1A	0.0212 (8)	0.0158 (7)	0.0170 (7)	0.0062 (6)	0.0022 (6)	0.0022 (5)
C2A	0.0295 (10)	0.0152 (7)	0.0217 (8)	0.0057 (7)	0.0019 (7)	0.0021 (6)
C3A	0.0274 (10)	0.0179 (7)	0.0231 (8)	0.0018 (7)	−0.0004 (7)	0.0034 (6)
C4A	0.0205 (9)	0.0229 (8)	0.0267 (9)	0.0033 (7)	0.0022 (7)	0.0047 (7)
C5A	0.0220 (9)	0.0209 (8)	0.0259 (8)	0.0076 (7)	0.0028 (7)	0.0051 (7)
C6A	0.0202 (8)	0.0150 (6)	0.0167 (7)	0.0055 (6)	0.0019 (6)	0.0018 (5)
C7A	0.0187 (8)	0.0151 (6)	0.0189 (7)	0.0067 (6)	0.0026 (6)	0.0027 (5)
C8A	0.0198 (8)	0.0126 (6)	0.0180 (7)	0.0055 (6)	−0.0002 (6)	0.0023 (5)
C9A	0.0269 (9)	0.0141 (7)	0.0255 (8)	0.0093 (6)	0.0020 (7)	0.0013 (6)
C10A	0.0304 (10)	0.0119 (7)	0.0344 (10)	0.0075 (7)	0.0004 (8)	0.0004 (7)
C11A	0.0249 (9)	0.0140 (7)	0.0322 (10)	0.0045 (6)	−0.0003 (7)	0.0054 (7)
C12A	0.0189 (8)	0.0165 (7)	0.0260 (8)	0.0051 (6)	0.0007 (6)	0.0065 (6)
C13A	0.0278 (10)	0.0204 (8)	0.0317 (10)	0.0062 (7)	0.0077 (8)	0.0085 (7)
I1B	0.02984 (7)	0.02357 (6)	0.01716 (6)	0.00598 (5)	0.00087 (4)	−0.00172 (4)
O1B	0.0255 (7)	0.0141 (6)	0.0585 (10)	0.0062 (5)	−0.0030 (7)	0.0086 (6)
N1B	0.0201 (7)	0.0113 (5)	0.0198 (6)	0.0037 (5)	0.0015 (5)	0.0023 (5)
N2B	0.0196 (7)	0.0167 (6)	0.0161 (6)	0.0040 (5)	0.0008 (5)	0.0026 (5)
C1B	0.0211 (8)	0.0171 (7)	0.0183 (7)	0.0057 (6)	0.0016 (6)	0.0010 (6)
C2B	0.0214 (8)	0.0192 (7)	0.0219 (8)	0.0029 (6)	0.0045 (6)	0.0016 (6)
C3B	0.0209 (9)	0.0184 (7)	0.0237 (8)	0.0017 (6)	0.0000 (6)	0.0000 (6)
C4B	0.0308 (10)	0.0172 (7)	0.0187 (8)	0.0024 (7)	−0.0008 (7)	−0.0004 (6)
C5B	0.0279 (9)	0.0169 (7)	0.0184 (7)	0.0054 (7)	0.0037 (6)	0.0032 (6)
C6B	0.0177 (8)	0.0129 (6)	0.0192 (7)	0.0040 (6)	0.0009 (6)	0.0026 (5)
C7B	0.0221 (8)	0.0142 (7)	0.0226 (8)	0.0053 (6)	0.0030 (6)	0.0034 (6)
C8B	0.0231 (8)	0.0128 (6)	0.0155 (7)	0.0031 (6)	0.0006 (6)	0.0028 (5)
C9B	0.0246 (9)	0.0132 (7)	0.0253 (8)	0.0037 (6)	−0.0006 (7)	0.0005 (6)
C10B	0.0320 (11)	0.0139 (7)	0.0265 (9)	0.0014 (7)	−0.0041 (8)	0.0014 (6)
C11B	0.0241 (9)	0.0190 (8)	0.0252 (9)	−0.0023 (7)	−0.0029 (7)	0.0036 (7)
C12B	0.0219 (9)	0.0206 (8)	0.0174 (7)	0.0023 (6)	−0.0002 (6)	0.0038 (6)
C13B	0.0203 (9)	0.0316 (10)	0.0284 (9)	0.0053 (8)	−0.0006 (7)	0.0023 (8)

I1A—C1A	2.0966 (18)	I1B—C1B	2.1027 (17)
O1A—C7A	1.226 (2)	O1B—C7B	1.221 (2)
N1A—C7A	1.363 (2)	N1B—C7B	1.354 (2)
N1A—C8A	1.414 (2)	N1B—C8B	1.404 (2)
N1A—H1NA	0.83 (3)	N1B—H1NB	0.84 (3)
N2A—C8A	1.342 (2)	N2B—C8B	1.337 (2)
N2A—C12A	1.350 (2)	N2B—C12B	1.351 (2)
C1A—C2A	1.397 (2)	C1B—C6B	1.388 (2)
C1A—C6A	1.398 (2)	C1B—C2B	1.389 (3)
C2A—C3A	1.386 (3)	C2B—C3B	1.389 (3)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.385 (3)	C3B—C4B	1.384 (3)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.388 (3)	C4B—C5B	1.395 (3)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.394 (3)	C5B—C6B	1.393 (2)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.503 (2)	C6B—C7B	1.507 (2)
C8A—C9A	1.387 (2)	C8B—C9B	1.393 (2)
C9A—C10A	1.384 (3)	C9B—C10B	1.389 (3)
C9A—H9AA	0.9300	C9B—H9BA	0.9300
C10A—C11A	1.379 (3)	C10B—C11B	1.381 (3)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.391 (3)	C11B—C12B	1.394 (3)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.492 (3)	C12B—C13B	1.493 (3)
C13A—H13A	0.9600	C13B—H13D	0.9600
C13A—H13B	0.9600	C13B—H13E	0.9600
C13A—H13C	0.9600	C13B—H13F	0.9600
C7A—N1A—C8A	125.92 (15)	C7B—N1B—C8B	125.89 (15)
C7A—N1A—H1NA	120.2 (18)	C7B—N1B—H1NB	120.7 (19)
C8A—N1A—H1NA	113.6 (18)	C8B—N1B—H1NB	113.4 (19)
C8A—N2A—C12A	117.99 (15)	C8B—N2B—C12B	118.81 (16)
C2A—C1A—C6A	120.10 (17)	C6B—C1B—C2B	121.01 (16)
C2A—C1A—I1A	119.55 (13)	C6B—C1B—I1B	120.61 (13)
C6A—C1A—I1A	120.14 (13)	C2B—C1B—I1B	118.26 (13)
C3A—C2A—C1A	119.77 (17)	C3B—C2B—C1B	119.29 (17)
C3A—C2A—H2AA	120.1	C3B—C2B—H2BA	120.4
C1A—C2A—H2AA	120.1	C1B—C2B—H2BA	120.4
C4A—C3A—C2A	120.51 (18)	C4B—C3B—C2B	120.32 (17)
C4A—C3A—H3AA	119.7	C4B—C3B—H3BA	119.8
C2A—C3A—H3AA	119.7	C2B—C3B—H3BA	119.8
C3A—C4A—C5A	119.77 (18)	C3B—C4B—C5B	120.11 (17)
C3A—C4A—H4AA	120.1	C3B—C4B—H4BA	119.9
C5A—C4A—H4AA	120.1	C5B—C4B—H4BA	119.9
C4A—C5A—C6A	120.64 (17)	C6B—C5B—C4B	119.94 (17)
C4A—C5A—H5AA	119.7	C6B—C5B—H5BA	120.0
C6A—C5A—H5AA	119.7	C4B—C5B—H5BA	120.0
C5A—C6A—C1A	119.12 (16)	C1B—C6B—C5B	119.29 (16)
C5A—C6A—C7A	118.07 (15)	C1B—C6B—C7B	120.77 (15)
C1A—C6A—C7A	122.80 (16)	C5B—C6B—C7B	119.71 (15)
O1A—C7A—N1A	124.45 (16)	O1B—C7B—N1B	125.15 (17)
O1A—C7A—C6A	121.70 (16)	O1B—C7B—C6B	119.13 (17)
N1A—C7A—C6A	113.81 (14)	N1B—C7B—C6B	115.71 (14)
N2A—C8A—C9A	123.90 (16)	N2B—C8B—C9B	123.56 (16)
N2A—C8A—N1A	113.34 (14)	N2B—C8B—N1B	113.63 (14)
C9A—C8A—N1A	122.70 (17)	C9B—C8B—N1B	122.78 (17)
C10A—C9A—C8A	117.33 (18)	C10B—C9B—C8B	117.12 (18)
C10A—C9A—H9AA	121.3	C10B—C9B—H9BA	121.4
C8A—C9A—H9AA	121.3	C8B—C9B—H9BA	121.4
C11A—C10A—C9A	119.90 (17)	C11B—C10B—C9B	120.02 (18)
C11A—C10A—H10A	120.1	C11B—C10B—H10B	120.0
C9A—C10A—H10A	120.1	C9B—C10B—H10B	120.0
C10A—C11A—C12A	119.28 (18)	C10B—C11B—C12B	119.32 (17)
C10A—C11A—H11A	120.4	C10B—C11B—H11B	120.3
C12A—C11A—H11A	120.4	C12B—C11B—H11B	120.3
N2A—C12A—C11A	121.60 (18)	N2B—C12B—C11B	121.10 (18)
N2A—C12A—C13A	117.44 (16)	N2B—C12B—C13B	116.96 (17)
C11A—C12A—C13A	120.95 (17)	C11B—C12B—C13B	121.93 (17)
C12A—C13A—H13A	109.5	C12B—C13B—H13D	109.5
C12A—C13A—H13B	109.5	C12B—C13B—H13E	109.5
H13A—C13A—H13B	109.5	H13D—C13B—H13E	109.5
C12A—C13A—H13C	109.5	C12B—C13B—H13F	109.5
H13A—C13A—H13C	109.5	H13D—C13B—H13F	109.5
H13B—C13A—H13C	109.5	H13E—C13B—H13F	109.5
C6A—C1A—C2A—C3A	1.4 (3)	C6B—C1B—C2B—C3B	−0.5 (3)
I1A—C1A—C2A—C3A	−173.36 (14)	I1B—C1B—C2B—C3B	175.59 (14)
C1A—C2A—C3A—C4A	1.3 (3)	C1B—C2B—C3B—C4B	−1.1 (3)
C2A—C3A—C4A—C5A	−2.2 (3)	C2B—C3B—C4B—C5B	1.3 (3)
C3A—C4A—C5A—C6A	0.4 (3)	C3B—C4B—C5B—C6B	0.0 (3)
C4A—C5A—C6A—C1A	2.2 (3)	C2B—C1B—C6B—C5B	1.8 (3)
C4A—C5A—C6A—C7A	−178.51 (17)	I1B—C1B—C6B—C5B	−174.20 (13)
C2A—C1A—C6A—C5A	−3.1 (3)	C2B—C1B—C6B—C7B	−172.64 (17)
I1A—C1A—C6A—C5A	171.60 (13)	I1B—C1B—C6B—C7B	11.3 (2)
C2A—C1A—C6A—C7A	177.67 (16)	C4B—C5B—C6B—C1B	−1.5 (3)
I1A—C1A—C6A—C7A	−7.6 (2)	C4B—C5B—C6B—C7B	172.96 (17)
C8A—N1A—C7A—O1A	0.8 (3)	C8B—N1B—C7B—O1B	−5.4 (3)
C8A—N1A—C7A—C6A	−176.93 (15)	C8B—N1B—C7B—C6B	175.15 (16)
C5A—C6A—C7A—O1A	−77.9 (2)	C1B—C6B—C7B—O1B	86.5 (2)
C1A—C6A—C7A—O1A	101.3 (2)	C5B—C6B—C7B—O1B	−87.9 (2)
C5A—C6A—C7A—N1A	99.94 (19)	C1B—C6B—C7B—N1B	−94.0 (2)
C1A—C6A—C7A—N1A	−80.8 (2)	C5B—C6B—C7B—N1B	91.6 (2)
C12A—N2A—C8A—C9A	0.1 (3)	C12B—N2B—C8B—C9B	−1.2 (3)
C12A—N2A—C8A—N1A	−177.17 (15)	C12B—N2B—C8B—N1B	177.04 (14)
C7A—N1A—C8A—N2A	−153.70 (16)	C7B—N1B—C8B—N2B	165.94 (16)
C7A—N1A—C8A—C9A	29.0 (3)	C7B—N1B—C8B—C9B	−15.8 (3)
N2A—C8A—C9A—C10A	0.0 (3)	N2B—C8B—C9B—C10B	−0.7 (3)
N1A—C8A—C9A—C10A	177.00 (17)	N1B—C8B—C9B—C10B	−178.83 (17)
C8A—C9A—C10A—C11A	−0.2 (3)	C8B—C9B—C10B—C11B	1.1 (3)
C9A—C10A—C11A—C12A	0.2 (3)	C9B—C10B—C11B—C12B	0.4 (3)
C8A—N2A—C12A—C11A	0.0 (3)	C8B—N2B—C12B—C11B	2.8 (3)
C8A—N2A—C12A—C13A	−179.40 (16)	C8B—N2B—C12B—C13B	−176.19 (16)
C10A—C11A—C12A—N2A	−0.1 (3)	C10B—C11B—C12B—N2B	−2.4 (3)
C10A—C11A—C12A—C13A	179.25 (17)	C10B—C11B—C12B—C13B	176.50 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1NA···N2Bi	0.83 (3)	2.14 (3)	2.962 (2)	172 (3)
N1B—H1NB···N2Ai	0.84 (3)	2.25 (3)	3.079 (2)	169 (2)
C9A—H9AA···O1A	0.93	2.40	2.895 (2)	113
C5B—H5BA···O1Aii	0.93	2.58	3.359 (2)	141
C9B—H9BA···O1B	0.93	2.26	2.825 (3)	118
C11A—H11A···O1Biii	0.93	2.48	3.254 (2)	141
C4B—H4BA···Cg1ii	0.93	2.71	3.565 (2)	153
C13A—H13C···Cg2i	0.96	2.85	3.629 (2)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1NA⋯N2Bi	0.83 (3)	2.14 (3)	2.962 (2)	172 (3)
N1B—H1NB⋯N2Ai	0.84 (3)	2.25 (3)	3.079 (2)	169 (2)
C9A—H9AA⋯O1A	0.93	2.40	2.895 (2)	113
C5B—H5BA⋯O1Aii	0.93	2.58	3.359 (2)	141
C9B—H9BA⋯O1B	0.93	2.26	2.825 (3)	118
C11A—H11A⋯O1Biii	0.93	2.48	3.254 (2)	141
C4B—H4BA⋯Cg1ii	0.93	2.71	3.565 (2)	153
C13A—H13C⋯Cg2i	0.96	2.85	3.629 (2)	139

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C1A–C6A and C1B–C6B rings, respectively.