Carbinoxaminium dipicrate.

In the dication of the title salt, C16H21ClN2O(2+)·2C6H2N3O7 (-) [systematic name: 2-{(4-chloro-phen-yl)[2-(di-methyl-aza-nium-yl)eth-oxy]meth-yl}pyridinium bis-(2,4,6-tri-nitro-phenolate), contains a carbinoxaminium dication and two picrate anions, which are held together through inter-molecular N-H⋯O hydrogen bonds. In the dication, the two aromatic rings form a dihedral angle of 80.1 (1)°. In the two independent picrate anions, the nitro groups are twisted from the benzene plane, the largest dihedral angle in each ion being 42.8 (1) and 81.1 (5)°. In the crystal, in addition to the classical N-H⋯O hydrogen bonds, weak C-H⋯O hydrogen bonds and π-π inter-actions between the aromatic rings of the anions [centroid-centroid distances of 3.5768 (15) and 3.7436 (15) Å] help to establish the packing.

Related literature

For the pharmacological importance of anti­histamines, see: Wagner (1962 ▶). For the effect of anti­histamines on psychomotor performance, see: Seppala et al. (1981 ▶). For related structures, see: Bertolasi et al. (1980 ▶); Parvez et al. (2001 ▶); Fun et al. (2010 ▶); Kaur et al. (2013 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H21ClN2O2+·2C6n class="Species">H2N3O7 −

M = 749.01

Triclinic,

a = 8.1719 (6) Å

b = 8.5341 (6) Å

c = 23.5868 (16) Å

α = 83.771 (6)°

β = 85.484 (6)°

γ = 74.827 (6)°

V = 1576.1 (2) Å3

Z = 2

Cu Kα radiation

μ = 1.87 mm−1

T = 173 K

0.24 × 0.16 × 0.12 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.871, T max = 1.000

9838 measured reflections

6071 independent reflections

4958 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.145

S = 1.02

6071 reflections

476 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813018886/cv5423sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018886/cv5423Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813018886/cv5423Isup3.cml

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

C16H21ClN2O2+·2C6H2N3O7−	Z = 2
Mr = 749.01	F(000) = 772
Triclinic, P1	Dx = 1.578 Mg m−3
a = 8.1719 (6) Å	Cu Kα radiation, λ = 1.54184 Å
b = 8.5341 (6) Å	Cell parameters from 3773 reflections
c = 23.5868 (16) Å	θ = 3.8–72.4°
α = 83.771 (6)°	µ = 1.87 mm−1
β = 85.484 (6)°	T = 173 K
γ = 74.827 (6)°	Prism, yellow
V = 1576.1 (2) Å3	0.24 × 0.16 × 0.12 mm

Agilent Xcalibur (Eos, Gemini) diffractometer	6071 independent reflections
Radiation source: Enhance (Cu) X-ray Source	4958 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1	Rint = 0.036
ω scans	θmax = 72.5°, θmin = 3.8°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	h = −9→10
Tmin = 0.871, Tmax = 1.000	k = −6→10
9838 measured reflections	l = −26→28

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.050	w = 1/[σ2(Fo2) + (0.0778P)2 + 0.3489P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.145	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.42 e Å−3
6071 reflections	Δρmin = −0.38 e Å−3
476 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0006 (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.

	x	y	z	Uiso*/Ueq
Cl1	−0.11261 (7)	1.50201 (7)	0.24701 (3)	0.04328 (18)
O1	0.66697 (18)	0.99915 (17)	0.25648 (6)	0.0256 (3)
N1	0.5260 (2)	0.8100 (2)	0.15238 (8)	0.0259 (4)
H1	0.555 (4)	0.868 (4)	0.1249 (13)	0.045 (8)*
N2	0.9121 (2)	0.9449 (2)	0.33517 (7)	0.0270 (4)
H2	0.8313	0.8739	0.3411	0.032*
C1	0.5639 (2)	1.0201 (2)	0.20923 (8)	0.0229 (4)
H1A	0.6251	1.0540	0.1735	0.027*
C2	0.3938 (3)	1.1451 (2)	0.21871 (9)	0.0232 (4)
C3	0.3387 (3)	1.1925 (3)	0.27286 (9)	0.0273 (4)
H3	0.4076	1.1482	0.3043	0.033*
C4	0.1838 (3)	1.3039 (3)	0.28151 (9)	0.0296 (5)
H4	0.1471	1.3382	0.3184	0.036*
C5	0.0832 (3)	1.3645 (3)	0.23545 (10)	0.0288 (5)
C6	0.1341 (3)	1.3170 (3)	0.18120 (10)	0.0304 (5)
H6	0.0630	1.3585	0.1501	0.037*
C7	0.2907 (3)	1.2077 (3)	0.17307 (9)	0.0274 (4)
H7	0.3281	1.1752	0.1360	0.033*
C8	0.5295 (2)	0.8557 (2)	0.20483 (9)	0.0232 (4)
C9	0.4844 (3)	0.6731 (3)	0.14378 (10)	0.0311 (5)
H9	0.4842	0.6444	0.1060	0.037*
C10	0.4421 (3)	0.5740 (3)	0.18928 (10)	0.0314 (5)
H10	0.4096	0.4783	0.1833	0.038*
C11	0.4475 (3)	0.6162 (3)	0.24404 (9)	0.0298 (5)
H11	0.4208	0.5479	0.2761	0.036*
C12	0.4921 (3)	0.7583 (2)	0.25224 (9)	0.0260 (4)
H12	0.4968	0.7879	0.2896	0.031*
C13	0.7505 (3)	1.1265 (3)	0.25669 (9)	0.0278 (4)
H13A	0.6705	1.2343	0.2480	0.033*
H13B	0.8467	1.1132	0.2278	0.033*
C14	0.8134 (3)	1.1129 (3)	0.31594 (9)	0.0285 (4)
H14A	0.8860	1.1890	0.3166	0.034*
H14B	0.7149	1.1464	0.3432	0.034*
C15	0.9831 (4)	0.9471 (3)	0.39156 (11)	0.0432 (6)
H15A	1.0624	1.0166	0.3871	0.065*
H15B	1.0429	0.8360	0.4054	0.065*
H15C	0.8903	0.9902	0.4191	0.065*
C16	1.0494 (3)	0.8722 (3)	0.29313 (11)	0.0375 (5)
H16A	0.9990	0.8586	0.2582	0.056*
H16B	1.1142	0.7656	0.3095	0.056*
H16C	1.1252	0.9444	0.2840	0.056*
O1A	0.6767 (2)	0.7783 (3)	0.37604 (7)	0.0510 (5)
O2A	0.9906 (3)	0.5583 (3)	0.38556 (9)	0.0628 (6)
O3A	0.9285 (3)	0.3338 (3)	0.41788 (10)	0.0648 (6)
O4A	0.6720 (2)	0.3773 (2)	0.61350 (7)	0.0384 (4)
O5A	0.4787 (3)	0.5957 (2)	0.63041 (7)	0.0499 (5)
O6A	0.2565 (3)	0.9728 (3)	0.47738 (9)	0.0603 (6)
O7A	0.4233 (4)	1.0273 (3)	0.40692 (9)	0.0810 (8)
N1A	0.9039 (3)	0.4822 (3)	0.41567 (9)	0.0450 (5)
N2A	0.5868 (2)	0.5149 (2)	0.59866 (8)	0.0323 (4)
N3A	0.3898 (3)	0.9401 (3)	0.44864 (9)	0.0467 (6)
C1A	0.6573 (3)	0.7231 (3)	0.42626 (9)	0.0360 (5)
C2A	0.7648 (3)	0.5717 (3)	0.45134 (10)	0.0348 (5)
C3A	0.7429 (3)	0.5018 (3)	0.50562 (9)	0.0328 (5)
H3A	0.8156	0.4001	0.5186	0.039*
C4A	0.6116 (3)	0.5837 (3)	0.54113 (9)	0.0288 (4)
C5A	0.4993 (3)	0.7266 (3)	0.52136 (9)	0.0306 (5)
H5A	0.4078	0.7790	0.5457	0.037*
C6A	0.5199 (3)	0.7930 (3)	0.46644 (9)	0.0333 (5)
O1B	0.5906 (2)	1.03134 (19)	0.07357 (7)	0.0357 (4)
O2B	0.5038 (3)	1.3996 (3)	0.06288 (11)	0.0659 (7)
O3B	0.7430 (4)	1.3352 (4)	0.09961 (11)	0.0893 (10)
O4B	1.0327 (4)	1.3210 (3)	−0.11434 (11)	0.0780 (8)
O5B	1.0417 (3)	1.0971 (3)	−0.14993 (8)	0.0573 (6)
O6B	0.8368 (2)	0.6875 (2)	−0.03911 (8)	0.0453 (5)
O7B	0.6563 (3)	0.7393 (2)	0.03210 (8)	0.0549 (6)
N1B	0.6504 (3)	1.3270 (2)	0.06334 (8)	0.0350 (4)
N2B	0.9919 (3)	1.1925 (3)	−0.11323 (9)	0.0426 (5)
N3B	0.7522 (3)	0.7805 (2)	−0.00549 (8)	0.0336 (4)
C1B	0.6833 (3)	1.0589 (3)	0.03035 (9)	0.0270 (4)
C2B	0.7212 (3)	1.2152 (3)	0.01923 (9)	0.0286 (4)
C3B	0.8166 (3)	1.2631 (3)	−0.02558 (9)	0.0308 (5)
H3B	0.8360	1.3689	−0.0299	0.037*
C4B	0.8853 (3)	1.1496 (3)	−0.06533 (9)	0.0304 (5)
C5B	0.8615 (3)	0.9943 (3)	−0.05819 (9)	0.0291 (5)
H5B	0.9116	0.9185	−0.0852	0.035*
C6B	0.7647 (3)	0.9490 (3)	−0.01178 (9)	0.0272 (4)

	U11	U22	U33	U12	U13	U23
Cl1	0.0298 (3)	0.0375 (3)	0.0553 (4)	0.0028 (2)	0.0052 (2)	−0.0063 (3)
O1	0.0273 (7)	0.0240 (7)	0.0269 (7)	−0.0089 (6)	−0.0051 (6)	−0.0002 (6)
N1	0.0313 (9)	0.0245 (9)	0.0216 (9)	−0.0076 (7)	0.0021 (7)	−0.0014 (7)
N2	0.0272 (9)	0.0278 (9)	0.0258 (9)	−0.0056 (7)	−0.0026 (7)	−0.0032 (7)
C1	0.0253 (10)	0.0231 (9)	0.0201 (9)	−0.0060 (8)	−0.0006 (7)	−0.0019 (7)
C2	0.0253 (10)	0.0203 (9)	0.0255 (10)	−0.0085 (8)	0.0002 (8)	−0.0027 (8)
C3	0.0280 (10)	0.0300 (11)	0.0247 (10)	−0.0091 (8)	−0.0018 (8)	−0.0024 (8)
C4	0.0314 (11)	0.0334 (11)	0.0249 (10)	−0.0100 (9)	0.0055 (8)	−0.0070 (9)
C5	0.0229 (10)	0.0230 (10)	0.0391 (12)	−0.0040 (8)	0.0043 (8)	−0.0051 (9)
C6	0.0291 (11)	0.0296 (11)	0.0327 (12)	−0.0068 (9)	−0.0056 (9)	−0.0019 (9)
C7	0.0318 (11)	0.0252 (10)	0.0256 (10)	−0.0066 (8)	−0.0012 (8)	−0.0055 (8)
C8	0.0196 (9)	0.0232 (9)	0.0256 (10)	−0.0032 (7)	0.0001 (7)	−0.0038 (8)
C9	0.0380 (12)	0.0285 (11)	0.0268 (11)	−0.0070 (9)	−0.0009 (9)	−0.0066 (9)
C10	0.0372 (12)	0.0233 (10)	0.0355 (12)	−0.0101 (9)	−0.0002 (9)	−0.0058 (9)
C11	0.0330 (11)	0.0265 (10)	0.0278 (11)	−0.0069 (9)	0.0017 (8)	0.0030 (8)
C12	0.0290 (10)	0.0260 (10)	0.0218 (10)	−0.0047 (8)	−0.0005 (8)	−0.0033 (8)
C13	0.0255 (10)	0.0251 (10)	0.0344 (11)	−0.0092 (8)	−0.0035 (8)	−0.0010 (8)
C14	0.0275 (10)	0.0245 (10)	0.0341 (11)	−0.0058 (8)	−0.0028 (8)	−0.0067 (9)
C15	0.0522 (15)	0.0412 (14)	0.0344 (13)	−0.0036 (11)	−0.0166 (11)	−0.0057 (11)
C16	0.0297 (12)	0.0378 (13)	0.0400 (13)	−0.0007 (10)	0.0022 (10)	−0.0051 (10)
O1A	0.0498 (11)	0.0875 (15)	0.0252 (9)	−0.0400 (11)	−0.0032 (7)	0.0092 (9)
O2A	0.0600 (13)	0.0879 (16)	0.0548 (12)	−0.0453 (12)	0.0332 (10)	−0.0307 (12)
O3A	0.0659 (14)	0.0592 (14)	0.0602 (14)	−0.0059 (11)	0.0231 (11)	−0.0100 (11)
O4A	0.0377 (9)	0.0383 (9)	0.0337 (9)	−0.0026 (7)	−0.0031 (7)	0.0050 (7)
O5A	0.0605 (12)	0.0493 (11)	0.0245 (9)	0.0068 (9)	0.0119 (8)	0.0020 (8)
O6A	0.0566 (13)	0.0600 (13)	0.0517 (12)	0.0047 (10)	−0.0095 (10)	0.0065 (10)
O7A	0.146 (3)	0.0492 (13)	0.0382 (12)	−0.0148 (15)	−0.0048 (13)	0.0148 (10)
N1A	0.0419 (12)	0.0678 (16)	0.0320 (11)	−0.0237 (11)	0.0082 (9)	−0.0171 (10)
N2A	0.0321 (10)	0.0389 (11)	0.0243 (9)	−0.0074 (8)	−0.0011 (7)	0.0000 (8)
N3A	0.0757 (17)	0.0401 (12)	0.0274 (11)	−0.0182 (11)	−0.0177 (11)	0.0027 (9)
C1A	0.0403 (13)	0.0547 (15)	0.0233 (11)	−0.0318 (11)	−0.0018 (9)	−0.0007 (10)
C2A	0.0324 (12)	0.0527 (14)	0.0254 (11)	−0.0205 (11)	0.0045 (9)	−0.0106 (10)
C3A	0.0312 (12)	0.0421 (13)	0.0275 (11)	−0.0132 (10)	−0.0007 (9)	−0.0053 (9)
C4A	0.0324 (11)	0.0355 (11)	0.0202 (10)	−0.0123 (9)	−0.0005 (8)	−0.0011 (8)
C5A	0.0348 (11)	0.0357 (12)	0.0230 (10)	−0.0117 (9)	−0.0016 (8)	−0.0030 (9)
C6A	0.0433 (13)	0.0361 (12)	0.0254 (11)	−0.0183 (10)	−0.0067 (9)	0.0001 (9)
O1B	0.0498 (10)	0.0294 (8)	0.0262 (8)	−0.0103 (7)	0.0101 (7)	−0.0037 (6)
O2B	0.0407 (11)	0.0705 (15)	0.0901 (17)	−0.0047 (10)	0.0063 (11)	−0.0533 (13)
O3B	0.0874 (18)	0.102 (2)	0.0667 (16)	0.0240 (15)	−0.0328 (14)	−0.0554 (15)
O4B	0.111 (2)	0.0569 (14)	0.0702 (15)	−0.0414 (14)	0.0510 (15)	−0.0147 (12)
O5B	0.0684 (14)	0.0647 (13)	0.0369 (10)	−0.0175 (11)	0.0225 (9)	−0.0134 (9)
O6B	0.0565 (11)	0.0355 (9)	0.0443 (10)	−0.0106 (8)	0.0101 (8)	−0.0175 (8)
O7B	0.0897 (16)	0.0415 (11)	0.0377 (10)	−0.0289 (11)	0.0213 (10)	−0.0097 (8)
N1B	0.0470 (12)	0.0279 (10)	0.0313 (10)	−0.0121 (9)	0.0048 (9)	−0.0072 (8)
N2B	0.0453 (12)	0.0437 (12)	0.0347 (11)	−0.0090 (10)	0.0115 (9)	−0.0019 (9)
N3B	0.0447 (11)	0.0316 (10)	0.0250 (9)	−0.0092 (8)	−0.0022 (8)	−0.0055 (8)
C1B	0.0310 (11)	0.0280 (10)	0.0209 (10)	−0.0050 (8)	−0.0020 (8)	−0.0025 (8)
C2B	0.0313 (11)	0.0278 (10)	0.0246 (10)	−0.0039 (8)	0.0010 (8)	−0.0041 (8)
C3B	0.0312 (11)	0.0294 (11)	0.0305 (11)	−0.0067 (9)	0.0002 (9)	−0.0012 (9)
C4B	0.0308 (11)	0.0349 (12)	0.0230 (10)	−0.0062 (9)	0.0021 (8)	0.0001 (9)
C5B	0.0308 (11)	0.0327 (11)	0.0213 (10)	−0.0022 (9)	−0.0022 (8)	−0.0059 (8)
C6B	0.0308 (11)	0.0273 (10)	0.0228 (10)	−0.0051 (8)	−0.0032 (8)	−0.0031 (8)

Cl1—C5	1.741 (2)	C16—H16A	0.9800
O1—C1	1.418 (2)	C16—H16B	0.9800
O1—C13	1.428 (2)	C16—H16C	0.9800
N1—H1	0.83 (3)	O1A—C1A	1.240 (3)
N1—C8	1.341 (3)	O2A—N1A	1.220 (3)
N1—C9	1.338 (3)	O3A—N1A	1.226 (3)
N2—H2	1.0000	O4A—N2A	1.227 (3)
N2—C14	1.491 (3)	O5A—N2A	1.227 (3)
N2—C15	1.496 (3)	O6A—N3A	1.220 (3)
N2—C16	1.490 (3)	O7A—N3A	1.226 (3)
C1—H1A	1.0000	N1A—C2A	1.455 (3)
C1—C2	1.532 (3)	N2A—C4A	1.440 (3)
C1—C8	1.517 (3)	N3A—C6A	1.463 (3)
C2—C3	1.387 (3)	C1A—C2A	1.454 (4)
C2—C7	1.392 (3)	C1A—C6A	1.456 (3)
C3—H3	0.9500	C2A—C3A	1.371 (3)
C3—C4	1.386 (3)	C3A—H3A	0.9500
C4—H4	0.9500	C3A—C4A	1.391 (3)
C4—C5	1.385 (3)	C4A—C5A	1.380 (3)
C5—C6	1.384 (3)	C5A—H5A	0.9500
C6—H6	0.9500	C5A—C6A	1.372 (3)
C6—C7	1.386 (3)	O1B—C1B	1.260 (3)
C7—H7	0.9500	O2B—N1B	1.196 (3)
C8—C12	1.382 (3)	O3B—N1B	1.205 (3)
C9—H9	0.9500	O4B—N2B	1.224 (3)
C9—C10	1.373 (3)	O5B—N2B	1.225 (3)
C10—H10	0.9500	O6B—N3B	1.225 (2)
C10—C11	1.385 (3)	O7B—N3B	1.221 (3)
C11—H11	0.9500	N1B—C2B	1.469 (3)
C11—C12	1.391 (3)	N2B—C4B	1.446 (3)
C12—H12	0.9500	N3B—C6B	1.459 (3)
C13—H13A	0.9900	C1B—C2B	1.439 (3)
C13—H13B	0.9900	C1B—C6B	1.443 (3)
C13—C14	1.509 (3)	C2B—C3B	1.355 (3)
C14—H14A	0.9900	C3B—H3B	0.9500
C14—H14B	0.9900	C3B—C4B	1.401 (3)
C15—H15A	0.9800	C4B—C5B	1.380 (3)
C15—H15B	0.9800	C5B—H5B	0.9500
C15—H15C	0.9800	C5B—C6B	1.380 (3)
C1—O1—C13	112.85 (15)	H15A—C15—H15B	109.5
C8—N1—H1	118 (2)	H15A—C15—H15C	109.5
C9—N1—H1	120 (2)	H15B—C15—H15C	109.5
C9—N1—C8	122.27 (19)	N2—C16—H16A	109.5
C14—N2—H2	107.7	N2—C16—H16B	109.5
C14—N2—C15	109.09 (17)	N2—C16—H16C	109.5
C15—N2—H2	107.7	H16A—C16—H16B	109.5
C16—N2—H2	107.7	H16A—C16—H16C	109.5
C16—N2—C14	113.72 (17)	H16B—C16—H16C	109.5
C16—N2—C15	110.69 (19)	O2A—N1A—O3A	123.5 (2)
O1—C1—H1A	110.2	O2A—N1A—C2A	118.5 (2)
O1—C1—C2	111.44 (15)	O3A—N1A—C2A	118.0 (2)
O1—C1—C8	106.13 (16)	O4A—N2A—C4A	118.84 (19)
C2—C1—H1A	110.2	O5A—N2A—O4A	122.87 (19)
C8—C1—H1A	110.2	O5A—N2A—C4A	118.27 (19)
C8—C1—C2	108.51 (16)	O6A—N3A—O7A	123.5 (3)
C3—C2—C1	120.58 (18)	O6A—N3A—C6A	118.3 (2)
C3—C2—C7	119.51 (19)	O7A—N3A—C6A	118.1 (3)
C7—C2—C1	119.87 (17)	O1A—C1A—C2A	123.5 (2)
C2—C3—H3	119.7	O1A—C1A—C6A	125.4 (3)
C4—C3—C2	120.5 (2)	C2A—C1A—C6A	111.06 (19)
C4—C3—H3	119.7	C1A—C2A—N1A	117.9 (2)
C3—C4—H4	120.5	C3A—C2A—N1A	116.6 (2)
C5—C4—C3	118.96 (19)	C3A—C2A—C1A	125.5 (2)
C5—C4—H4	120.5	C2A—C3A—H3A	120.8
C4—C5—Cl1	118.57 (17)	C2A—C3A—C4A	118.3 (2)
C6—C5—Cl1	119.81 (18)	C4A—C3A—H3A	120.8
C6—C5—C4	121.6 (2)	C3A—C4A—N2A	119.7 (2)
C5—C6—H6	120.6	C5A—C4A—N2A	119.2 (2)
C5—C6—C7	118.7 (2)	C5A—C4A—C3A	121.1 (2)
C7—C6—H6	120.6	C4A—C5A—H5A	120.0
C2—C7—H7	119.7	C6A—C5A—C4A	119.9 (2)
C6—C7—C2	120.67 (19)	C6A—C5A—H5A	120.0
C6—C7—H7	119.7	C1A—C6A—N3A	120.1 (2)
N1—C8—C1	117.61 (18)	C5A—C6A—N3A	115.8 (2)
N1—C8—C12	119.82 (19)	C5A—C6A—C1A	124.0 (2)
C12—C8—C1	122.46 (18)	O2B—N1B—O3B	123.5 (2)
N1—C9—H9	119.8	O2B—N1B—C2B	118.9 (2)
N1—C9—C10	120.3 (2)	O3B—N1B—C2B	117.5 (2)
C10—C9—H9	119.8	O4B—N2B—O5B	122.8 (2)
C9—C10—H10	120.6	O4B—N2B—C4B	118.2 (2)
C9—C10—C11	118.8 (2)	O5B—N2B—C4B	119.0 (2)
C11—C10—H10	120.6	O6B—N3B—C6B	117.99 (19)
C10—C11—H11	120.0	O7B—N3B—O6B	123.0 (2)
C10—C11—C12	120.1 (2)	O7B—N3B—C6B	118.96 (19)
C12—C11—H11	120.0	O1B—C1B—C2B	119.94 (19)
C8—C12—C11	118.64 (19)	O1B—C1B—C6B	127.9 (2)
C8—C12—H12	120.7	C2B—C1B—C6B	112.14 (19)
C11—C12—H12	120.7	C1B—C2B—N1B	113.88 (18)
O1—C13—H13A	110.5	C3B—C2B—N1B	119.5 (2)
O1—C13—H13B	110.5	C3B—C2B—C1B	126.6 (2)
O1—C13—C14	106.08 (17)	C2B—C3B—H3B	121.5
H13A—C13—H13B	108.7	C2B—C3B—C4B	116.9 (2)
C14—C13—H13A	110.5	C4B—C3B—H3B	121.5
C14—C13—H13B	110.5	C3B—C4B—N2B	119.4 (2)
N2—C14—C13	113.08 (16)	C5B—C4B—N2B	119.0 (2)
N2—C14—H14A	109.0	C5B—C4B—C3B	121.5 (2)
N2—C14—H14B	109.0	C4B—C5B—H5B	120.0
C13—C14—H14A	109.0	C6B—C5B—C4B	120.00 (19)
C13—C14—H14B	109.0	C6B—C5B—H5B	120.0
H14A—C14—H14B	107.8	C1B—C6B—N3B	120.33 (19)
N2—C15—H15A	109.5	C5B—C6B—N3B	116.93 (18)
N2—C15—H15B	109.5	C5B—C6B—C1B	122.7 (2)
N2—C15—H15C	109.5
Cl1—C5—C6—C7	179.84 (16)	O6A—N3A—C6A—C1A	162.2 (2)
O1—C1—C2—C3	−15.7 (3)	O6A—N3A—C6A—C5A	−15.9 (3)
O1—C1—C2—C7	166.52 (17)	O7A—N3A—C6A—C1A	−20.6 (3)
O1—C1—C8—N1	−142.31 (17)	O7A—N3A—C6A—C5A	161.2 (2)
O1—C1—C8—C12	41.7 (2)	N1A—C2A—C3A—C4A	179.83 (19)
O1—C13—C14—N2	50.9 (2)	N2A—C4A—C5A—C6A	−179.3 (2)
N1—C8—C12—C11	−1.5 (3)	C1A—C2A—C3A—C4A	−2.6 (3)
N1—C9—C10—C11	−1.7 (3)	C2A—C1A—C6A—N3A	−175.87 (19)
C1—O1—C13—C14	164.84 (16)	C2A—C1A—C6A—C5A	2.1 (3)
C1—C2—C3—C4	−179.11 (19)	C2A—C3A—C4A—N2A	−179.0 (2)
C1—C2—C7—C6	177.94 (18)	C2A—C3A—C4A—C5A	3.9 (3)
C1—C8—C12—C11	174.37 (19)	C3A—C4A—C5A—C6A	−2.3 (3)
C2—C1—C8—N1	97.8 (2)	C4A—C5A—C6A—N3A	177.1 (2)
C2—C1—C8—C12	−78.2 (2)	C4A—C5A—C6A—C1A	−1.0 (3)
C2—C3—C4—C5	1.4 (3)	C6A—C1A—C2A—N1A	177.21 (19)
C3—C2—C7—C6	0.2 (3)	C6A—C1A—C2A—C3A	−0.3 (3)
C3—C4—C5—Cl1	179.02 (16)	O1B—C1B—C2B—N1B	2.9 (3)
C3—C4—C5—C6	−0.3 (3)	O1B—C1B—C2B—C3B	−179.1 (2)
C4—C5—C6—C7	−0.9 (3)	O1B—C1B—C6B—N3B	−3.4 (4)
C5—C6—C7—C2	0.9 (3)	O1B—C1B—C6B—C5B	178.8 (2)
C7—C2—C3—C4	−1.3 (3)	O2B—N1B—C2B—C1B	−79.9 (3)
C8—N1—C9—C10	0.5 (3)	O2B—N1B—C2B—C3B	102.0 (3)
C8—C1—C2—C3	100.8 (2)	O3B—N1B—C2B—C1B	97.2 (3)
C8—C1—C2—C7	−77.0 (2)	O3B—N1B—C2B—C3B	−80.9 (3)
C9—N1—C8—C1	−174.95 (19)	O4B—N2B—C4B—C3B	7.3 (4)
C9—N1—C8—C12	1.2 (3)	O4B—N2B—C4B—C5B	−169.1 (3)
C9—C10—C11—C12	1.2 (3)	O5B—N2B—C4B—C3B	−174.9 (2)
C10—C11—C12—C8	0.4 (3)	O5B—N2B—C4B—C5B	8.6 (4)
C13—O1—C1—C2	−79.0 (2)	O6B—N3B—C6B—C1B	−172.9 (2)
C13—O1—C1—C8	163.01 (16)	O6B—N3B—C6B—C5B	5.0 (3)
C15—N2—C14—C13	174.50 (19)	O7B—N3B—C6B—C1B	8.3 (3)
C16—N2—C14—C13	50.4 (2)	O7B—N3B—C6B—C5B	−173.8 (2)
O1A—C1A—C2A—N1A	1.1 (3)	N1B—C2B—C3B—C4B	178.0 (2)
O1A—C1A—C2A—C3A	−176.5 (2)	N2B—C4B—C5B—C6B	177.9 (2)
O1A—C1A—C6A—N3A	0.2 (3)	C1B—C2B—C3B—C4B	0.1 (4)
O1A—C1A—C6A—C5A	178.2 (2)	C2B—C1B—C6B—N3B	175.34 (19)
O2A—N1A—C2A—C1A	43.5 (3)	C2B—C1B—C6B—C5B	−2.5 (3)
O2A—N1A—C2A—C3A	−138.8 (3)	C2B—C3B—C4B—N2B	−178.4 (2)
O3A—N1A—C2A—C1A	−137.1 (3)	C2B—C3B—C4B—C5B	−2.0 (3)
O3A—N1A—C2A—C3A	40.7 (3)	C3B—C4B—C5B—C6B	1.6 (3)
O4A—N2A—C4A—C3A	−7.0 (3)	C4B—C5B—C6B—N3B	−177.0 (2)
O4A—N2A—C4A—C5A	170.1 (2)	C4B—C5B—C6B—C1B	0.9 (3)
O5A—N2A—C4A—C3A	174.4 (2)	C6B—C1B—C2B—N1B	−175.96 (18)
O5A—N2A—C4A—C5A	−8.5 (3)	C6B—C1B—C2B—C3B	2.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1B	0.83 (3)	1.81 (3)	2.628 (2)	167 (3)
N2—H2···O1A	1.00	1.78	2.737 (3)	159
C1—H1A···O1B	1.00	2.43	3.183 (2)	132
C3—H3···O7A	0.95	2.53	3.366 (3)	148
C9—H9···O2Bi	0.95	2.38	3.137 (3)	136
C9—H9···O7B	0.95	2.36	2.956 (3)	120
C11—H11···O5Aii	0.95	2.49	3.309 (3)	144
C12—H12···O1A	0.95	2.59	3.430 (3)	148
C14—H14B···O5Aiii	0.99	2.46	3.253 (3)	137
C15—H15B···O4Aiv	0.98	2.59	3.400 (3)	140
C16—H16A···O5Bv	0.98	2.58	3.483 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1B	0.83 (3)	1.81 (3)	2.628 (2)	167 (3)
N2—H2⋯O1A	1.00	1.78	2.737 (3)	159
C1—H1A⋯O1B	1.00	2.43	3.183 (2)	132
C3—H3⋯O7A	0.95	2.53	3.366 (3)	148
C9—H9⋯O2B i	0.95	2.38	3.137 (3)	136
C9—H9⋯O7B	0.95	2.36	2.956 (3)	120
C11—H11⋯O5A ii	0.95	2.49	3.309 (3)	144
C12—H12⋯O1A	0.95	2.59	3.430 (3)	148
C14—H14B⋯O5A iii	0.99	2.46	3.253 (3)	137
C15—H15B⋯O4A iv	0.98	2.59	3.400 (3)	140
C16—H16A⋯O5B v	0.98	2.58	3.483 (3)	154

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