4-(Naphthalene-2-carboxamido)-pyridin-1-ium thio-cyanate-N-(pyridin-4-yl)naphthalene-2-carboxamide (1/1).

The asymmetric unit of the title compound, C(16)H(13)N(2)O(+)·NCS(-)·C(16)H(12)N(2)O, contains two N-(pyridin-4-yl)naphthalene-2-carboxamide mol-ecules, both are partially protonated in the pyridine moiety, i.e. the H atom attached to the pyridine N atom is partially occupied with an occupancy factor of 0.61 (3) and 0.39 (3), respectively. In the crystal, protonated and neutral N-(pyridin-4-yl)naphthalene-2-carboxamide mol-ecules are linked by N-H⋯N hydrogen bonding; the thio-cyanate counter-ion links with both protonated and neutral N-(pyridin-4-yl)naphthalene-2-carboxamide mol-ecules via N-H⋯S and N-H⋯N hydrogen bonding. The dihedral angles between the pyridine ring and naphthalene ring systems are 11.33 (6) and 9.51 (6)°, respectively. π-π stacking is observed in the crystal structure, the shortest centroid-centroid distance being 3.5929 (8) Å. The crystal structure was determined from a nonmerohedral twin {ratio of the twin components = 0.357 (1):0.643 (1) and twin law [-100 0-10 -101]}.

Related literature

For background to the biological activity of N-substituted benzamides and their applications in synthesis, see: Saeed et al. (2011 ▶); Priya et al. (2005 ▶). For related structures and use in mol­ecular recognition, see: Toda et al. (1987 ▶); Saeed et al. (2011 ▶, 2012 ▶). For bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H13N2O+·NCS−·C16H12N2O

M = 555.64

Triclinic,

a = 8.2667 (4) Å

b = 12.9008 (7) Å

c = 13.5579 (8) Å

α = 84.047 (5)°

β = 77.566 (5)°

γ = 71.684 (5)°

V = 1339.45 (13) Å3

Z = 2

Cu Kα radiation

μ = 1.41 mm−1

T = 123 K

0.38 × 0.35 × 0.29 mm

Data collection

Xcalibur (Ruby, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis RED; Agilent, 2011 ▶)T min = 0.904, T max = 1.000

9408 measured reflections

9408 independent reflections

8399 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.137

S = 1.02

9408 reflections

374 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812039864/xu5617sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039864/xu5617Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812039864/xu5617Isup3.cml

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

C16H13N2O+·NCS−·C16H12N2O	Z = 2
Mr = 555.64	F(000) = 580
Triclinic, P1	Dx = 1.378 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 8.2667 (4) Å	Cell parameters from 3931 reflections
b = 12.9008 (7) Å	θ = 3.3–75.5°
c = 13.5579 (8) Å	µ = 1.41 mm−1
α = 84.047 (5)°	T = 123 K
β = 77.566 (5)°	Prism, colorless
γ = 71.684 (5)°	0.38 × 0.35 × 0.29 mm
V = 1339.45 (13) Å3

Xcalibur (Ruby, Gemini) diffractometer	9408 independent reflections
Radiation source: Enhance (Cu) X-ray Source	8399 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
Detector resolution: 10.5081 pixels mm-1	θmax = 76.0°, θmin = 3.3°
ω scans	h = −10→10
Absorption correction: multi-scan [CrysAlis RED (Agilent, 2011) based on expressions derived from Clark & Reid (1995)]	k = −16→16
Tmin = 0.904, Tmax = 1.000	l = −12→16
9408 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0899P)2 + 0.2899P] where P = (Fo2 + 2Fc2)/3
9408 reflections	(Δ/σ)max = 0.001
374 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Experimental. CrysAlis RED, (Agilent, 2011) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm (Clark & Reid, 1995).

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	Occ. (<1)
S1S	0.08493 (5)	0.80651 (3)	0.97576 (3)	0.03396 (11)
N1S	0.4395 (2)	0.68666 (11)	0.95127 (10)	0.0399 (3)
C1S	0.2927 (2)	0.73545 (11)	0.96208 (10)	0.0315 (3)
O1A	0.66272 (14)	0.64980 (8)	0.56439 (7)	0.0319 (2)
N1A	0.58653 (14)	0.61521 (8)	0.73364 (8)	0.0240 (2)
H1AA	0.5779	0.6394	0.7935	0.034 (4)*
N2A	0.44101 (14)	0.33301 (8)	0.74169 (8)	0.0245 (2)
H2AA	0.4093	0.2735	0.7445	0.029*	0.61 (3)
C1A	0.68983 (17)	0.77349 (10)	0.67251 (10)	0.0245 (3)
C2A	0.66122 (17)	0.81223 (11)	0.76696 (10)	0.0263 (3)
H2AB	0.6133	0.7745	0.8239	0.032*
C3A	0.70214 (18)	0.90814 (11)	0.78109 (11)	0.0276 (3)
C4A	0.6715 (2)	0.94936 (12)	0.87865 (12)	0.0358 (3)
H4AA	0.6243	0.9120	0.9362	0.043*
C5A	0.7098 (2)	1.04289 (13)	0.89019 (14)	0.0412 (4)
H5AA	0.6893	1.0700	0.9557	0.049*
C6A	0.7797 (2)	1.09912 (12)	0.80502 (14)	0.0401 (4)
H6AA	0.8058	1.1638	0.8138	0.048*
C7A	0.81019 (19)	1.06170 (12)	0.71064 (13)	0.0356 (3)
H7AA	0.8561	1.1009	0.6541	0.043*
C8A	0.77348 (17)	0.96363 (11)	0.69583 (11)	0.0277 (3)
C9A	0.80472 (18)	0.92153 (11)	0.59920 (11)	0.0295 (3)
H9AA	0.8545	0.9577	0.5416	0.035*
C10A	0.76400 (17)	0.82912 (10)	0.58763 (10)	0.0268 (3)
H10A	0.7856	0.8019	0.5221	0.032*
C11A	0.64576 (16)	0.67468 (10)	0.65080 (10)	0.0239 (3)
C12A	0.53898 (16)	0.52088 (10)	0.73240 (10)	0.0218 (2)
C13A	0.53009 (17)	0.47683 (10)	0.64435 (10)	0.0242 (3)
H13A	0.5583	0.5106	0.5800	0.029*
C14A	0.47968 (17)	0.38366 (10)	0.65253 (10)	0.0256 (3)
H14A	0.4721	0.3544	0.5928	0.031*
C15A	0.45085 (19)	0.37358 (11)	0.82714 (10)	0.0281 (3)
H15A	0.4240	0.3371	0.8902	0.034*
C16A	0.49897 (18)	0.46677 (11)	0.82490 (10)	0.0273 (3)
H16A	0.5050	0.4942	0.8859	0.033*
O1B	0.27783 (14)	−0.15477 (8)	0.54771 (7)	0.0330 (2)
N1B	0.21021 (14)	−0.12707 (8)	0.71690 (8)	0.0225 (2)
H1BA	0.1676	−0.1533	0.7758	0.034 (4)*
N2B	0.35165 (14)	0.15425 (8)	0.73472 (8)	0.0242 (2)
H2BB	0.3810	0.2132	0.7397	0.029*	0.39 (3)
C1B	0.16169 (16)	−0.28346 (10)	0.65252 (10)	0.0221 (2)
C2B	0.10170 (17)	−0.32263 (10)	0.74599 (10)	0.0242 (3)
H2BA	0.0943	−0.2846	0.8040	0.029*
C3B	0.05008 (17)	−0.41902 (10)	0.75834 (10)	0.0255 (3)
C4B	−0.0151 (2)	−0.45925 (13)	0.85460 (12)	0.0357 (3)
H4BA	−0.0282	−0.4202	0.9129	0.043*
C5B	−0.0597 (2)	−0.55389 (13)	0.86471 (13)	0.0401 (4)
H5BA	−0.1037	−0.5800	0.9298	0.048*
C6B	−0.0404 (2)	−0.61291 (12)	0.77879 (14)	0.0376 (4)
H6BA	−0.0690	−0.6795	0.7867	0.045*
C7B	0.01863 (19)	−0.57544 (11)	0.68477 (12)	0.0322 (3)
H7BA	0.0299	−0.6157	0.6275	0.039*
C8B	0.06374 (16)	−0.47632 (10)	0.67138 (11)	0.0257 (3)
C9B	0.12318 (18)	−0.43331 (11)	0.57536 (11)	0.0277 (3)
H9BA	0.1309	−0.4701	0.5166	0.033*
C10B	0.16984 (17)	−0.33960 (10)	0.56551 (10)	0.0255 (3)
H10B	0.2081	−0.3116	0.5001	0.031*
C11B	0.22166 (16)	−0.18353 (10)	0.63304 (9)	0.0221 (2)
C12B	0.25886 (16)	−0.03295 (10)	0.71828 (10)	0.0212 (2)
C13B	0.34762 (17)	0.01249 (10)	0.63456 (10)	0.0239 (3)
H13B	0.3773	−0.0193	0.5705	0.029*
C14B	0.39169 (17)	0.10469 (11)	0.64657 (10)	0.0259 (3)
H14B	0.4536	0.1345	0.5894	0.031*
C15B	0.26547 (18)	0.11074 (11)	0.81480 (10)	0.0273 (3)
H15B	0.2363	0.1450	0.8777	0.033*
C16B	0.21700 (18)	0.01874 (11)	0.81046 (10)	0.0267 (3)
H16B	0.1560	−0.0094	0.8692	0.032*

	U11	U22	U33	U12	U13	U23
S1S	0.0457 (2)	0.03312 (19)	0.02666 (18)	−0.02096 (15)	0.00028 (14)	−0.00364 (13)
N1S	0.0512 (9)	0.0364 (7)	0.0346 (7)	−0.0163 (6)	−0.0070 (6)	−0.0049 (5)
C1S	0.0538 (10)	0.0279 (6)	0.0200 (6)	−0.0233 (7)	−0.0048 (6)	−0.0025 (5)
O1A	0.0463 (6)	0.0275 (5)	0.0268 (5)	−0.0190 (4)	−0.0050 (4)	−0.0023 (4)
N1A	0.0306 (6)	0.0186 (5)	0.0273 (5)	−0.0111 (4)	−0.0076 (4)	−0.0040 (4)
N2A	0.0276 (5)	0.0188 (5)	0.0303 (6)	−0.0107 (4)	−0.0064 (4)	−0.0020 (4)
C1A	0.0235 (6)	0.0179 (6)	0.0335 (7)	−0.0069 (5)	−0.0073 (5)	−0.0014 (5)
C2A	0.0284 (6)	0.0225 (6)	0.0302 (7)	−0.0107 (5)	−0.0066 (5)	0.0005 (5)
C3A	0.0281 (6)	0.0230 (6)	0.0340 (7)	−0.0076 (5)	−0.0105 (5)	−0.0018 (5)
C4A	0.0432 (8)	0.0308 (7)	0.0394 (8)	−0.0149 (6)	−0.0129 (7)	−0.0057 (6)
C5A	0.0468 (9)	0.0340 (8)	0.0512 (10)	−0.0151 (7)	−0.0186 (7)	−0.0111 (7)
C6A	0.0384 (8)	0.0248 (7)	0.0664 (11)	−0.0117 (6)	−0.0223 (7)	−0.0106 (7)
C7A	0.0323 (7)	0.0240 (6)	0.0549 (9)	−0.0119 (6)	−0.0134 (7)	0.0001 (6)
C8A	0.0238 (6)	0.0228 (6)	0.0384 (7)	−0.0070 (5)	−0.0103 (5)	0.0000 (5)
C9A	0.0298 (7)	0.0243 (6)	0.0349 (7)	−0.0106 (5)	−0.0061 (6)	0.0038 (5)
C10A	0.0282 (6)	0.0224 (6)	0.0294 (7)	−0.0078 (5)	−0.0053 (5)	−0.0002 (5)
C11A	0.0233 (6)	0.0163 (5)	0.0332 (7)	−0.0068 (5)	−0.0068 (5)	−0.0010 (5)
C12A	0.0216 (6)	0.0171 (5)	0.0280 (6)	−0.0064 (4)	−0.0059 (5)	−0.0022 (5)
C13A	0.0281 (6)	0.0229 (6)	0.0255 (6)	−0.0119 (5)	−0.0065 (5)	−0.0017 (5)
C14A	0.0303 (6)	0.0230 (6)	0.0276 (6)	−0.0121 (5)	−0.0067 (5)	−0.0038 (5)
C15A	0.0361 (7)	0.0245 (6)	0.0266 (6)	−0.0132 (5)	−0.0073 (5)	0.0010 (5)
C16A	0.0363 (7)	0.0251 (6)	0.0235 (6)	−0.0122 (5)	−0.0063 (5)	−0.0032 (5)
O1B	0.0489 (6)	0.0308 (5)	0.0251 (5)	−0.0232 (4)	−0.0024 (4)	−0.0017 (4)
N1B	0.0290 (5)	0.0188 (5)	0.0229 (5)	−0.0128 (4)	−0.0041 (4)	0.0003 (4)
N2B	0.0276 (5)	0.0176 (5)	0.0303 (6)	−0.0109 (4)	−0.0051 (4)	−0.0017 (4)
C1B	0.0224 (6)	0.0181 (6)	0.0275 (6)	−0.0068 (4)	−0.0072 (5)	−0.0018 (5)
C2B	0.0292 (6)	0.0216 (6)	0.0259 (6)	−0.0110 (5)	−0.0085 (5)	−0.0018 (5)
C3B	0.0277 (6)	0.0217 (6)	0.0308 (7)	−0.0109 (5)	−0.0098 (5)	0.0025 (5)
C4B	0.0457 (8)	0.0344 (7)	0.0343 (8)	−0.0219 (6)	−0.0118 (6)	0.0063 (6)
C5B	0.0481 (9)	0.0370 (8)	0.0442 (9)	−0.0261 (7)	−0.0158 (7)	0.0148 (7)
C6B	0.0366 (8)	0.0232 (6)	0.0605 (10)	−0.0167 (6)	−0.0187 (7)	0.0096 (6)
C7B	0.0310 (7)	0.0212 (6)	0.0495 (8)	−0.0102 (5)	−0.0143 (6)	−0.0027 (6)
C8B	0.0229 (6)	0.0186 (6)	0.0376 (7)	−0.0064 (5)	−0.0098 (5)	−0.0014 (5)
C9B	0.0297 (7)	0.0238 (6)	0.0317 (7)	−0.0083 (5)	−0.0065 (5)	−0.0079 (5)
C10B	0.0288 (6)	0.0232 (6)	0.0258 (6)	−0.0088 (5)	−0.0049 (5)	−0.0040 (5)
C11B	0.0249 (6)	0.0194 (6)	0.0238 (6)	−0.0088 (5)	−0.0052 (5)	−0.0011 (5)
C12B	0.0225 (6)	0.0175 (5)	0.0259 (6)	−0.0077 (4)	−0.0072 (5)	−0.0002 (4)
C13B	0.0290 (6)	0.0223 (6)	0.0234 (6)	−0.0124 (5)	−0.0041 (5)	−0.0014 (5)
C14B	0.0287 (6)	0.0237 (6)	0.0276 (6)	−0.0128 (5)	−0.0040 (5)	0.0007 (5)
C15B	0.0320 (7)	0.0244 (6)	0.0280 (7)	−0.0133 (5)	−0.0015 (5)	−0.0059 (5)
C16B	0.0314 (7)	0.0255 (6)	0.0252 (6)	−0.0145 (5)	−0.0007 (5)	−0.0013 (5)

S1S—C1S	1.6530 (17)	C16A—H16A	0.9500
N1S—C1S	1.163 (2)	O1B—C11B	1.2163 (16)
O1A—C11A	1.2141 (17)	N1B—C11B	1.3836 (16)
N1A—C11A	1.3822 (17)	N1B—C12B	1.3969 (15)
N1A—C12A	1.3941 (15)	N1B—H1BA	0.8800
N1A—H1AA	0.8800	N2B—C15B	1.3392 (17)
N2A—C14A	1.3384 (17)	N2B—C14B	1.3424 (17)
N2A—C15A	1.3476 (17)	N2B—H2BB	0.8800
N2A—H2AA	0.8800	C1B—C2B	1.3642 (18)
C1A—C2A	1.3688 (19)	C1B—C10B	1.4258 (17)
C1A—C10A	1.4201 (19)	C1B—C11B	1.5007 (17)
C1A—C11A	1.5035 (17)	C2B—C3B	1.4199 (17)
C2A—C3A	1.4220 (18)	C2B—H2BA	0.9500
C2A—H2AB	0.9500	C3B—C4B	1.413 (2)
C3A—C8A	1.413 (2)	C3B—C8B	1.4213 (19)
C3A—C4A	1.419 (2)	C4B—C5B	1.368 (2)
C4A—C5A	1.372 (2)	C4B—H4BA	0.9500
C4A—H4AA	0.9500	C5B—C6B	1.411 (2)
C5A—C6A	1.413 (3)	C5B—H5BA	0.9500
C5A—H5AA	0.9500	C6B—C7B	1.360 (2)
C6A—C7A	1.359 (2)	C6B—H6BA	0.9500
C6A—H6AA	0.9500	C7B—C8B	1.4247 (18)
C7A—C8A	1.4330 (19)	C7B—H7BA	0.9500
C7A—H7AA	0.9500	C8B—C9B	1.411 (2)
C8A—C9A	1.411 (2)	C9B—C10B	1.3659 (18)
C9A—C10A	1.3685 (19)	C9B—H9BA	0.9500
C9A—H9AA	0.9500	C10B—H10B	0.9500
C10A—H10A	0.9500	C12B—C13B	1.3943 (17)
C12A—C16A	1.3981 (18)	C12B—C16B	1.4029 (18)
C12A—C13A	1.3993 (17)	C13B—C14B	1.3828 (17)
C13A—C14A	1.3777 (17)	C13B—H13B	0.9500
C13A—H13A	0.9500	C14B—H14B	0.9500
C14A—H14A	0.9500	C15B—C16B	1.3770 (18)
C15A—C16A	1.3757 (18)	C15B—H15B	0.9500
C15A—H15A	0.9500	C16B—H16B	0.9500
N1S—C1S—S1S	178.91 (14)	C11B—N1B—C12B	127.11 (11)
C11A—N1A—C12A	126.84 (11)	C11B—N1B—H1BA	116.4
C11A—N1A—H1AA	116.6	C12B—N1B—H1BA	116.4
C12A—N1A—H1AA	116.6	C15B—N2B—C14B	117.55 (11)
C14A—N2A—C15A	119.63 (11)	C15B—N2B—H2BB	121.2
C14A—N2A—H2AA	120.2	C14B—N2B—H2BB	121.2
C15A—N2A—H2AA	120.2	C2B—C1B—C10B	119.21 (11)
C2A—C1A—C10A	119.38 (12)	C2B—C1B—C11B	124.68 (11)
C2A—C1A—C11A	124.32 (12)	C10B—C1B—C11B	116.11 (11)
C10A—C1A—C11A	116.29 (12)	C1B—C2B—C3B	121.33 (12)
C1A—C2A—C3A	121.01 (12)	C1B—C2B—H2BA	119.3
C1A—C2A—H2AB	119.5	C3B—C2B—H2BA	119.3
C3A—C2A—H2AB	119.5	C4B—C3B—C2B	121.82 (12)
C8A—C3A—C4A	119.61 (13)	C4B—C3B—C8B	119.12 (12)
C8A—C3A—C2A	119.03 (12)	C2B—C3B—C8B	119.06 (12)
C4A—C3A—C2A	121.36 (13)	C5B—C4B—C3B	120.68 (15)
C5A—C4A—C3A	120.27 (15)	C5B—C4B—H4BA	119.7
C5A—C4A—H4AA	119.9	C3B—C4B—H4BA	119.7
C3A—C4A—H4AA	119.9	C4B—C5B—C6B	120.25 (15)
C4A—C5A—C6A	120.28 (15)	C4B—C5B—H5BA	119.9
C4A—C5A—H5AA	119.9	C6B—C5B—H5BA	119.9
C6A—C5A—H5AA	119.9	C7B—C6B—C5B	120.65 (13)
C7A—C6A—C5A	120.78 (13)	C7B—C6B—H6BA	119.7
C7A—C6A—H6AA	119.6	C5B—C6B—H6BA	119.7
C5A—C6A—H6AA	119.6	C6B—C7B—C8B	120.55 (14)
C6A—C7A—C8A	120.49 (15)	C6B—C7B—H7BA	119.7
C6A—C7A—H7AA	119.8	C8B—C7B—H7BA	119.7
C8A—C7A—H7AA	119.8	C9B—C8B—C3B	118.65 (12)
C9A—C8A—C3A	119.19 (12)	C9B—C8B—C7B	122.67 (13)
C9A—C8A—C7A	122.24 (14)	C3B—C8B—C7B	118.68 (13)
C3A—C8A—C7A	118.57 (13)	C10B—C9B—C8B	121.09 (12)
C10A—C9A—C8A	120.63 (13)	C10B—C9B—H9BA	119.5
C10A—C9A—H9AA	119.7	C8B—C9B—H9BA	119.5
C8A—C9A—H9AA	119.7	C9B—C10B—C1B	120.62 (12)
C9A—C10A—C1A	120.75 (13)	C9B—C10B—H10B	119.7
C9A—C10A—H10A	119.6	C1B—C10B—H10B	119.7
C1A—C10A—H10A	119.6	O1B—C11B—N1B	122.34 (11)
O1A—C11A—N1A	122.82 (11)	O1B—C11B—C1B	121.19 (11)
O1A—C11A—C1A	120.67 (12)	N1B—C11B—C1B	116.47 (11)
N1A—C11A—C1A	116.51 (11)	C13B—C12B—N1B	124.48 (11)
N1A—C12A—C16A	117.80 (11)	C13B—C12B—C16B	117.79 (11)
N1A—C12A—C13A	124.03 (12)	N1B—C12B—C16B	117.72 (11)
C16A—C12A—C13A	118.16 (11)	C14B—C13B—C12B	118.76 (12)
C14A—C13A—C12A	118.88 (12)	C14B—C13B—H13B	120.6
C14A—C13A—H13A	120.6	C12B—C13B—H13B	120.6
C12A—C13A—H13A	120.6	N2B—C14B—C13B	123.50 (12)
N2A—C14A—C13A	122.28 (12)	N2B—C14B—H14B	118.3
N2A—C14A—H14A	118.9	C13B—C14B—H14B	118.3
C13A—C14A—H14A	118.9	N2B—C15B—C16B	123.19 (12)
N2A—C15A—C16A	121.34 (12)	N2B—C15B—H15B	118.4
N2A—C15A—H15A	119.3	C16B—C15B—H15B	118.4
C16A—C15A—H15A	119.3	C15B—C16B—C12B	119.21 (12)
C15A—C16A—C12A	119.70 (12)	C15B—C16B—H16B	120.4
C15A—C16A—H16A	120.1	C12B—C16B—H16B	120.4
C12A—C16A—H16A	120.1
C10A—C1A—C2A—C3A	1.0 (2)	C10B—C1B—C2B—C3B	1.06 (19)
C11A—C1A—C2A—C3A	−178.25 (12)	C11B—C1B—C2B—C3B	−178.88 (11)
C1A—C2A—C3A—C8A	0.0 (2)	C1B—C2B—C3B—C4B	−178.85 (13)
C1A—C2A—C3A—C4A	179.46 (13)	C1B—C2B—C3B—C8B	0.88 (19)
C8A—C3A—C4A—C5A	0.4 (2)	C2B—C3B—C4B—C5B	−178.25 (14)
C2A—C3A—C4A—C5A	−179.09 (14)	C8B—C3B—C4B—C5B	2.0 (2)
C3A—C4A—C5A—C6A	0.1 (2)	C3B—C4B—C5B—C6B	0.2 (2)
C4A—C5A—C6A—C7A	0.0 (2)	C4B—C5B—C6B—C7B	−1.5 (2)
C5A—C6A—C7A—C8A	−0.6 (2)	C5B—C6B—C7B—C8B	0.6 (2)
C4A—C3A—C8A—C9A	179.51 (13)	C4B—C3B—C8B—C9B	177.77 (13)
C2A—C3A—C8A—C9A	−0.98 (19)	C2B—C3B—C8B—C9B	−1.97 (18)
C4A—C3A—C8A—C7A	−1.1 (2)	C4B—C3B—C8B—C7B	−2.89 (19)
C2A—C3A—C8A—C7A	178.46 (12)	C2B—C3B—C8B—C7B	177.37 (12)
C6A—C7A—C8A—C9A	−179.41 (13)	C6B—C7B—C8B—C9B	−179.07 (13)
C6A—C7A—C8A—C3A	1.2 (2)	C6B—C7B—C8B—C3B	1.6 (2)
C3A—C8A—C9A—C10A	1.1 (2)	C3B—C8B—C9B—C10B	1.13 (19)
C7A—C8A—C9A—C10A	−178.35 (13)	C7B—C8B—C9B—C10B	−178.18 (13)
C8A—C9A—C10A—C1A	−0.1 (2)	C8B—C9B—C10B—C1B	0.8 (2)
C2A—C1A—C10A—C9A	−0.9 (2)	C2B—C1B—C10B—C9B	−1.93 (19)
C11A—C1A—C10A—C9A	178.39 (12)	C11B—C1B—C10B—C9B	178.01 (12)
C12A—N1A—C11A—O1A	0.2 (2)	C12B—N1B—C11B—O1B	−0.2 (2)
C12A—N1A—C11A—C1A	−179.59 (11)	C12B—N1B—C11B—C1B	179.44 (11)
C2A—C1A—C11A—O1A	174.42 (13)	C2B—C1B—C11B—O1B	178.11 (13)
C10A—C1A—C11A—O1A	−4.83 (18)	C10B—C1B—C11B—O1B	−1.83 (18)
C2A—C1A—C11A—N1A	−5.75 (19)	C2B—C1B—C11B—N1B	−1.58 (18)
C10A—C1A—C11A—N1A	175.00 (11)	C10B—C1B—C11B—N1B	178.48 (11)
C11A—N1A—C12A—C16A	173.68 (12)	C11B—N1B—C12B—C13B	−8.2 (2)
C11A—N1A—C12A—C13A	−5.9 (2)	C11B—N1B—C12B—C16B	172.51 (12)
N1A—C12A—C13A—C14A	−179.35 (12)	N1B—C12B—C13B—C14B	−178.54 (12)
C16A—C12A—C13A—C14A	1.12 (18)	C16B—C12B—C13B—C14B	0.80 (18)
C15A—N2A—C14A—C13A	0.1 (2)	C15B—N2B—C14B—C13B	0.5 (2)
C12A—C13A—C14A—N2A	−0.9 (2)	C12B—C13B—C14B—N2B	−0.9 (2)
C14A—N2A—C15A—C16A	0.4 (2)	C14B—N2B—C15B—C16B	0.0 (2)
N2A—C15A—C16A—C12A	−0.1 (2)	N2B—C15B—C16B—C12B	0.0 (2)
N1A—C12A—C16A—C15A	179.78 (12)	C13B—C12B—C16B—C15B	−0.39 (19)
C13A—C12A—C16A—C15A	−0.65 (19)	N1B—C12B—C16B—C15B	179.00 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1AA···N1S	0.88	2.24	3.0576 (17)	154
N1B—H1BA···S1Si	0.88	2.69	3.5345 (11)	162
N2A—H2AA···N2B	0.88	1.77	2.6492 (15)	173
N2B—H2BB···N2A	0.88	1.77	2.6492 (15)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1AA⋯N1S	0.88	2.24	3.0576 (17)	154
N1B—H1BA⋯S1S i	0.88	2.69	3.5345 (11)	162
N2A—H2AA⋯N2B	0.88	1.77	2.6492 (15)	173
N2B—H2BB⋯N2A	0.88	1.77	2.6492 (15)	177

Symmetry code: (i) .