Phenyl-ring rotational disorder in the two-dimensional hydrogen-bonded structure of the 1:1 proton-transfer salt of the diazo-dye precursor 4-(phenyl­diazenyl)aniline (aniline yellow) with L-tartaric acid

In the structure of the 1:1 proton-transfer compound from the reaction of L-tartaric acid with the azo-dye precursor aniline yellow [4-(phenyl­­diazenyl)aniline], namely 4-(phenyl­di­az­enyl)­anilinium (2R,3R)-3-carb­oxy-2,3-dihy­droxy­propano­ate, C₁₂H₁₂N₃⁺·C₄H₅O₆⁻, the asymmetric unit contains two independent 4-(phenyl­diazenyl)­anilinium cations and two hydrogen L-tartrate anions. The structure is unusual in that all four phenyl rings of the two cations have identical rotational disorder with equal occupancy of the conformations. The two hydrogen L-tartrate anions form independent but similar chains through head-to-tail carboxyl–carboxyl­ate O—H...O hydrogen bonds [graph set C(7)], which are then extended into a two-dimensional hydrogen-bonded sheet structure through hy­droxy O—H...O hydrogen-bonded links. The anilinium groups of the 4-(phenyl­diazenyl)­anilinium cations are incorporated into the sheets and also provide inter­nal hydrogen-bonded extensions, while their aromatic tails are layered in the structure without significant association except for weak π–π inter­actions [minimum ring centroid separation = 3.844 (3) Å]. The hydrogen L-tartrate residues of both anions exhibit the common short intra­molecular hy­droxy–carboxylate O—H...O hydogen bonds. This work provides a solution to the unusual disorder problem inherent in the structure of this salt, as well as giving another example of the utility of the hydrogen tartrate anion in the generation of sheet substructures in mol­ecular assembly processes.

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

4-(phenyldiazenyl)anilinium (2R,3R)-3-carboxy-2,3-dihydroxypropanoate

Crystal data

C12H12N3^+·C4H5O6^−	Z = 2
Mr = 347.33	F(000) = 364
Triclinic, P1	Dx = 1.456 Mg m^−3
Hall symbol: P 1	Melting point: 467 K
a = 6.1710 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.4134 (3) Å	Cell parameters from 7191 reflections
c = 18.2438 (6) Å	θ = 2.9–32.2°
α = 91.754 (3)°	µ = 0.11 mm^−1
β = 91.308 (3)°	T = 200 K
γ = 108.135 (4)°	Plate, orange-red
V = 792.33 (6) Å^3	0.30 × 0.20 × 0.15 mm

Data collection

Oxford Gemini-S CCD detector diffractometer	4174 independent reflections
Radiation source: Enhance (Mo) X-ray source	3593 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
ω scans	θmax = 29.0°, θmin = 2.9°
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	h = −8→8
Tmin = 0.874, Tmax = 0.980	k = −10→10
16695 measured reflections	l = −24→24

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.118	H-atom parameters not refined
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0802P)^2] where P = (Fo^2 + 2Fc^2)/3
4174 reflections	(Δ/σ)max < 0.001
432 parameters	Δρmax = 0.43 e Å^−3
3 restraints	Δρmin = −0.31 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1C	−0.0628 (5)	0.5384 (4)	0.08229 (15)	0.0322 (8)
N4C	−0.1760 (4)	0.5383 (3)	0.38852 (12)	0.0195 (6)
N11C	0.1379 (5)	0.5723 (4)	0.06254 (15)	0.0347 (8)
C1C	−0.0825 (5)	0.5374 (4)	0.16033 (17)	0.0272 (8)
C2C	−0.2964 (11)	0.4571 (11)	0.1863 (4)	0.0281 (14)*	0.500
C2E	−0.2957 (11)	0.5296 (11)	0.1872 (4)	0.0280 (14)*	0.500
C3C	−0.3319 (11)	0.4563 (11)	0.2614 (3)	0.0246 (13)*	0.500
C3E	−0.3281 (11)	0.5288 (10)	0.2630 (3)	0.0248 (13)*	0.500
C4C	−0.1479 (4)	0.5351 (3)	0.30893 (15)	0.0203 (7)
C5C	0.0709 (10)	0.6190 (10)	0.2837 (3)	0.0249 (12)*	0.500
C5E	0.0633 (11)	0.5398 (10)	0.2840 (3)	0.0261 (12)*	0.500
C6C	0.1044 (11)	0.6185 (10)	0.2089 (3)	0.0257 (12)*	0.500
C6E	0.0963 (11)	0.5392 (10)	0.2092 (3)	0.0253 (12)*	0.500
C11C	0.1642 (5)	0.5787 (4)	−0.01519 (16)	0.0286 (9)
C21C	−0.0058 (11)	0.5805 (11)	−0.0652 (3)	0.0272 (13)*	0.500
C21E	−0.0111 (12)	0.5046 (11)	−0.0658 (4)	0.0306 (14)*	0.500
C31C	0.0419 (12)	0.5946 (11)	−0.1387 (4)	0.0290 (13)*	0.500
C31E	0.0316 (13)	0.5164 (12)	−0.1397 (4)	0.0367 (16)*	0.500
C41C	0.2509 (6)	0.5998 (5)	−0.16274 (18)	0.0369 (10)
C51C	0.4195 (12)	0.5862 (10)	−0.1126 (4)	0.0320 (13)*	0.500
C51E	0.4278 (13)	0.6804 (12)	−0.1130 (4)	0.0380 (15)*	0.500
C61C	0.3743 (11)	0.5748 (10)	−0.0377 (4)	0.0307 (13)*	0.500
C61E	0.3888 (13)	0.6694 (12)	−0.0382 (4)	0.0384 (15)*	0.500
N1D	0.1669 (5)	0.0823 (4)	1.00283 (14)	0.0313 (8)
N4D	0.3820 (4)	0.1221 (3)	0.70360 (12)	0.0198 (6)
N11D	−0.0375 (5)	0.0488 (4)	1.01770 (15)	0.0329 (8)
C1D	0.2072 (5)	0.0879 (4)	0.92596 (16)	0.0262 (8)
C2D	0.0388 (10)	0.0771 (10)	0.8706 (3)	0.0209 (12)*	0.500
C2F	0.0402 (11)	0.0105 (11)	0.8723 (3)	0.0235 (13)*	0.500
C3D	0.0959 (10)	0.0889 (9)	0.7979 (3)	0.0186 (11)*	0.500
C3F	0.0972 (11)	0.0211 (10)	0.7994 (3)	0.0236 (13)*	0.500
C4D	0.3178 (4)	0.1069 (4)	0.77999 (15)	0.0196 (7)
C5D	0.4805 (10)	0.1031 (9)	0.8320 (3)	0.0246 (12)*	0.500
C5F	0.4912 (10)	0.1944 (10)	0.8347 (3)	0.0254 (12)*	0.500
C6D	0.4246 (10)	0.0911 (9)	0.9050 (3)	0.0248 (12)*	0.500
C6F	0.4348 (10)	0.1835 (10)	0.9080 (3)	0.0261 (12)*	0.500
C11D	−0.0770 (5)	0.0432 (4)	1.09485 (16)	0.0280 (8)
C21D	0.0920 (6)	0.1248 (5)	1.14872 (16)	0.0329 (14)*	0.500
C21F	0.0835 (11)	0.0406 (9)	1.1472 (3)	0.0300 (13)*	0.500
C31D	0.0351 (12)	0.1183 (12)	1.2218 (4)	0.0366 (15)*	0.500
C31F	0.0244 (12)	0.0279 (11)	1.2198 (4)	0.0331 (14)*	0.500
C41D	−0.1885 (6)	0.0245 (5)	1.24124 (16)	0.0390 (10)
C51D	−0.3557 (13)	−0.0581 (12)	1.1884 (4)	0.0390 (15)*	0.500
C51F	−0.3483 (12)	0.0325 (11)	1.1886 (4)	0.0333 (14)*	0.500
C61D	−0.3000 (12)	−0.0492 (11)	1.1149 (4)	0.0347 (14)*	0.500
C61F	−0.2934 (11)	0.0419 (10)	1.1142 (4)	0.0301 (13)*	0.500
O2A	−0.3622 (3)	0.5088 (3)	0.69950 (11)	0.0228 (5)
O3A	0.1018 (3)	0.7150 (3)	0.66547 (12)	0.0276 (6)
O11A	−0.4098 (3)	0.8420 (3)	0.68346 (12)	0.0260 (6)
O12A	−0.1931 (3)	0.9075 (3)	0.58533 (11)	0.0258 (6)
O41A	−0.2114 (3)	0.2534 (3)	0.59407 (12)	0.0249 (6)
O42A	0.1255 (4)	0.3572 (3)	0.65412 (15)	0.0391 (8)
C1A	−0.2955 (4)	0.8008 (4)	0.63381 (14)	0.0179 (7)
C2A	−0.2911 (4)	0.5935 (3)	0.63153 (14)	0.0176 (7)
C3A	−0.0536 (4)	0.5847 (3)	0.61653 (15)	0.0178 (7)
C4A	−0.0376 (4)	0.3851 (4)	0.62462 (14)	0.0187 (7)
O2B	0.0297 (3)	−0.0729 (3)	0.41205 (12)	0.0250 (6)
O3B	0.2806 (3)	0.0322 (3)	0.54840 (10)	0.0231 (5)
O11B	0.0018 (3)	0.2667 (3)	0.43520 (13)	0.0280 (6)
O12B	0.3787 (3)	0.4087 (3)	0.43645 (13)	0.0288 (6)
O41B	0.3136 (3)	−0.2980 (3)	0.49378 (12)	0.0263 (6)
O42B	0.5627 (3)	−0.1540 (3)	0.41079 (11)	0.0235 (6)
C1B	0.2011 (5)	0.2653 (4)	0.43131 (15)	0.0195 (7)
C2B	0.2408 (4)	0.0740 (3)	0.41817 (14)	0.0173 (7)
C3B	0.3850 (4)	0.0350 (3)	0.48092 (14)	0.0164 (7)
C4B	0.4333 (4)	−0.1496 (4)	0.45930 (15)	0.0174 (7)
H2C	−0.42140	0.40170	0.15280	0.0340*	0.500
H2E	−0.41850	0.52500	0.15400	0.0340*	0.500
H3C	−0.48030	0.40230	0.27950	0.0300*	0.500
H3E	−0.47180	0.52390	0.28190	0.0300*	0.500
H5C	0.19510	0.67560	0.31730	0.0300*	0.500
H5E	0.18430	0.54340	0.31780	0.0310*	0.500
H6C	0.25270	0.67260	0.19070	0.0310*	0.500
H6E	0.23980	0.53990	0.19110	0.0300*	0.500
H21C	−0.15400	0.57200	−0.04930	0.0330*	0.500
H21E	−0.16150	0.44520	−0.05000	0.0370*	0.500
H31C	−0.07310	0.60080	−0.17320	0.0350*	0.500
H31E	−0.09020	0.46710	−0.17490	0.0440*	0.500
H41C	0.28230	0.61270	−0.21340	0.0440*
H42C	−0.10420	0.66280	0.40940	0.0230*
H43C	−0.10720	0.47180	0.41060	0.0230*
H44C	−0.32420	0.50280	0.39770	0.0230*
H51C	0.56370	0.58460	−0.12920	0.0380*	0.500
H51E	0.57610	0.74340	−0.12960	0.0460*	0.500
H61C	0.48660	0.56460	−0.00300	0.0370*	0.500
H61E	0.51040	0.72160	−0.00320	0.0460*	0.500
H2D	−0.11400	0.06180	0.88350	0.0250*	0.500
H2F	−0.11290	−0.04970	0.88530	0.0280*	0.500
H3D	−0.01570	0.08470	0.76060	0.0220*	0.500
H3F	−0.01770	−0.03170	0.76240	0.0280*	0.500
H5D	0.62970	0.10880	0.81800	0.0300*	0.500
H5F	0.64250	0.25890	0.82110	0.0310*	0.500
H6D	0.53490	0.08490	0.94120	0.0300*	0.500
H6F	0.54720	0.23930	0.94550	0.0310*	0.500
H21D	0.24480	0.18490	1.13540	0.0400*	0.500
H21F	0.23360	0.04730	1.13390	0.0360*	0.500
H31D	0.14800	0.17760	1.25870	0.0440*	0.500
H31F	0.13440	0.02140	1.25610	0.0400*	0.500
H41D	−0.22550	0.01760	1.29160	0.0470*
H42D	0.46920	0.23880	0.69710	0.0240*
H43D	0.25720	0.09080	0.67210	0.0240*
H44D	0.45720	0.05180	0.69310	0.0240*
H51D	−0.50760	−0.12050	1.20200	0.0470*	0.500
H51F	−0.49590	0.03170	1.20260	0.0400*	0.500
H61D	−0.41440	−0.10640	1.07810	0.0420*	0.500
H61F	−0.40320	0.04730	1.07770	0.0360*	0.500
H2A	−0.39880	0.52020	0.59150	0.0210*
H3A	−0.01560	0.62400	0.56520	0.0210*
H41A	−0.2060	0.15040	0.59690	0.0300*
H21A	−0.35990	0.59440	0.72470	0.0270*
H31A	0.23760	0.74820	0.67020	0.0330*
H2B	0.32300	0.07650	0.37140	0.0210*
H3B	0.53370	0.13980	0.48390	0.0200*
H21B	−0.06320	−0.02630	0.41980	0.0300*
H31B	0.14920	−0.00260	0.55870	0.0280*
H41B	0.32850	−0.39200	0.47470	0.0320*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1C	0.0307 (13)	0.0394 (15)	0.0258 (13)	0.0100 (11)	0.0020 (10)	0.0007 (10)
N4C	0.0145 (10)	0.0191 (10)	0.0258 (12)	0.0065 (8)	0.0014 (8)	0.0005 (8)
N11C	0.0296 (13)	0.0492 (17)	0.0259 (13)	0.0133 (12)	0.0021 (11)	−0.0017 (12)
C1C	0.0250 (14)	0.0276 (14)	0.0291 (15)	0.0087 (11)	−0.0007 (12)	−0.0008 (11)
C4C	0.0211 (13)	0.0148 (11)	0.0249 (13)	0.0055 (10)	0.0029 (10)	0.0005 (9)
C11C	0.0299 (15)	0.0303 (15)	0.0260 (15)	0.0101 (12)	0.0011 (12)	−0.0008 (12)
C41C	0.0434 (19)	0.0467 (19)	0.0258 (16)	0.0208 (16)	0.0063 (14)	0.0058 (14)
N1D	0.0300 (13)	0.0437 (15)	0.0207 (12)	0.0117 (12)	0.0036 (10)	0.0052 (10)
N4D	0.0182 (10)	0.0223 (11)	0.0211 (11)	0.0093 (8)	0.0033 (9)	0.0028 (8)
N11D	0.0302 (13)	0.0429 (15)	0.0253 (13)	0.0107 (12)	0.0046 (10)	0.0030 (11)
C1D	0.0260 (14)	0.0319 (15)	0.0211 (14)	0.0094 (12)	0.0042 (11)	0.0031 (11)
C4D	0.0202 (12)	0.0205 (12)	0.0194 (12)	0.0081 (10)	0.0018 (10)	0.0002 (10)
C11D	0.0312 (15)	0.0302 (15)	0.0215 (14)	0.0078 (12)	0.0019 (11)	0.0018 (11)
C41D	0.054 (2)	0.0444 (19)	0.0234 (15)	0.0210 (17)	0.0122 (15)	0.0065 (13)
O2A	0.0203 (9)	0.0205 (9)	0.0296 (10)	0.0084 (7)	0.0094 (8)	0.0057 (7)
O3A	0.0127 (8)	0.0202 (9)	0.0470 (13)	0.0019 (7)	−0.0048 (8)	−0.0036 (8)
O11A	0.0270 (10)	0.0234 (10)	0.0322 (11)	0.0136 (8)	0.0113 (8)	0.0027 (8)
O12A	0.0263 (10)	0.0216 (9)	0.0334 (11)	0.0122 (8)	0.0080 (8)	0.0073 (8)
O41A	0.0212 (9)	0.0178 (9)	0.0372 (11)	0.0089 (7)	−0.0050 (8)	−0.0015 (8)
O42A	0.0288 (11)	0.0310 (12)	0.0620 (16)	0.0180 (10)	−0.0176 (11)	−0.0047 (10)
C1A	0.0118 (10)	0.0194 (12)	0.0242 (13)	0.0075 (9)	−0.0020 (10)	0.0013 (10)
C2A	0.0125 (11)	0.0182 (12)	0.0228 (13)	0.0057 (9)	−0.0006 (9)	0.0018 (10)
C3A	0.0128 (11)	0.0178 (11)	0.0237 (13)	0.0058 (9)	0.0027 (9)	0.0015 (9)
C4A	0.0169 (11)	0.0242 (12)	0.0174 (12)	0.0093 (10)	0.0046 (9)	0.0025 (9)
O2B	0.0157 (9)	0.0170 (9)	0.0419 (12)	0.0053 (7)	−0.0058 (8)	−0.0037 (8)
O3B	0.0220 (9)	0.0284 (10)	0.0191 (9)	0.0083 (8)	0.0035 (7)	−0.0014 (7)
O11B	0.0181 (9)	0.0220 (10)	0.0464 (13)	0.0094 (8)	0.0032 (9)	0.0059 (9)
O12B	0.0202 (9)	0.0152 (9)	0.0514 (13)	0.0051 (7)	0.0106 (9)	0.0030 (8)
O41B	0.0252 (10)	0.0168 (9)	0.0385 (12)	0.0077 (8)	0.0132 (9)	0.0035 (8)
O42B	0.0187 (9)	0.0215 (9)	0.0316 (11)	0.0077 (7)	0.0083 (8)	0.0024 (8)
C1B	0.0236 (13)	0.0154 (11)	0.0221 (13)	0.0089 (10)	0.0080 (10)	0.0052 (9)
C2B	0.0145 (11)	0.0168 (11)	0.0211 (12)	0.0053 (9)	0.0033 (9)	0.0013 (9)
C3B	0.0135 (11)	0.0151 (11)	0.0200 (12)	0.0040 (9)	−0.0007 (9)	−0.0008 (9)
C4B	0.0111 (10)	0.0184 (11)	0.0227 (13)	0.0047 (9)	−0.0003 (9)	0.0002 (9)

Geometric parameters (Å, º)

O2A—C2A	1.423 (3)	C6C—H6C	0.9500
O3A—C3A	1.408 (3)	C6E—H6E	0.9500
O11A—C1A	1.248 (3)	C21C—H21C	0.9500
O12A—C1A	1.251 (3)	C21E—H21E	0.9500
O41A—C4A	1.305 (3)	C31C—H31C	0.9500
O42A—C4A	1.207 (4)	C31E—H31E	0.9500
O2A—H21A	0.7700	C41C—H41C	0.9500
O3A—H31A	0.8000	C51C—H51C	0.9500
O41A—H41A	0.7800	C51E—H51E	0.9500
O2B—C2B	1.414 (3)	C61C—H61C	0.9500
O3B—C3B	1.400 (3)	C61E—H61E	0.9500
O11B—C1B	1.237 (4)	C1D—C2F	1.379 (7)
O12B—C1B	1.267 (4)	C1D—C2D	1.415 (7)
O41B—C4B	1.307 (3)	C1D—C6F	1.414 (7)
O42B—C4B	1.212 (3)	C1D—C6D	1.397 (7)
O2B—H21B	0.7700	C2D—C3D	1.379 (8)
O3B—H31B	0.8000	C2F—C3F	1.382 (8)
O41B—H41B	0.8000	C3D—C4D	1.382 (7)
N1C—C1C	1.432 (4)	C3F—C4D	1.371 (8)
N1C—N11C	1.249 (4)	C4D—C5F	1.429 (7)
N4C—C4C	1.467 (4)	C4D—C5D	1.373 (7)
N11C—C11C	1.432 (4)	C5D—C6D	1.382 (8)
N4C—H44C	0.8900	C5F—C6F	1.388 (8)
N4C—H43C	0.8500	C11D—C61F	1.386 (8)
N4C—H42C	0.9500	C11D—C21F	1.365 (7)
N1D—C1D	1.430 (4)	C11D—C61D	1.396 (8)
N1D—N11D	1.245 (4)	C11D—C21D	1.394 (5)
N4D—C4D	1.456 (4)	C21D—C31D	1.385 (8)
N11D—C11D	1.434 (4)	C21F—C31F	1.380 (9)
N4D—H42D	0.8800	C31D—C41D	1.398 (9)
N4D—H44D	0.8200	C31F—C41D	1.372 (9)
N4D—H43D	0.9200	C41D—C51F	1.377 (8)
C1C—C6E	1.399 (7)	C41D—C51D	1.376 (9)
C1C—C2C	1.370 (8)	C51D—C61D	1.390 (10)
C1C—C2E	1.399 (8)	C51F—C61F	1.405 (10)
C1C—C6C	1.402 (7)	C2D—H2D	0.9500
C2C—C3C	1.392 (9)	C2F—H2F	0.9500
C2E—C3E	1.402 (9)	C3D—H3D	0.9500
C3C—C4C	1.376 (7)	C3F—H3F	0.9500
C3E—C4C	1.365 (7)	C5D—H5D	0.9500
C4C—C5E	1.381 (7)	C5F—H5F	0.9500
C4C—C5C	1.395 (7)	C6D—H6D	0.9500
C5C—C6C	1.385 (8)	C6F—H6F	0.9500
C5E—C6E	1.384 (8)	C21D—H21D	0.9500
C11C—C61E	1.419 (9)	C21F—H21F	0.9500
C11C—C21C	1.378 (7)	C31D—H31D	0.9500
C11C—C61C	1.378 (8)	C31F—H31F	0.9500
C11C—C21E	1.370 (8)	C41D—H41D	0.9500
C21C—C31C	1.380 (9)	C51D—H51D	0.9500
C21E—C31E	1.380 (10)	C51F—H51F	0.9500
C31C—C41C	1.361 (9)	C61D—H61D	0.9500
C31E—C41C	1.383 (9)	C61F—H61F	0.9500
C41C—C51E	1.374 (9)	C1A—C2A	1.545 (4)
C41C—C51C	1.399 (8)	C2A—C3A	1.518 (4)
C51C—C61C	1.401 (10)	C3A—C4A	1.525 (4)
C51E—C61E	1.392 (10)	C2A—H2A	1.0000
C2C—H2C	0.9500	C3A—H3A	1.0000
C2E—H2E	0.9500	C1B—C2B	1.525 (4)
C3C—H3C	0.9500	C2B—C3B	1.523 (4)
C3E—H3E	0.9500	C3B—C4B	1.531 (4)
C5C—H5C	0.9500	C2B—H2B	1.0000
C5E—H5E	0.9500	C3B—H3B	1.0000
C2A—O2A—H21A	103.00	N1D—C1D—C2D	124.5 (4)
C3A—O3A—H31A	133.00	N1D—C1D—C2F	123.9 (4)
C4A—O41A—H41A	115.00	C2D—C1D—C6D	118.6 (4)
C2B—O2B—H21B	107.00	N1D—C1D—C6D	116.7 (3)
C3B—O3B—H31B	131.00	C2F—C1D—C6F	121.4 (4)
C4B—O41B—H41B	109.00	C1D—C2D—C3D	120.2 (6)
N11C—N1C—C1C	113.2 (3)	C1D—C2F—C3F	119.5 (6)
N1C—N11C—C11C	114.7 (3)	C2D—C3D—C4D	119.1 (5)
H42C—N4C—H43C	103.00	C2F—C3F—C4D	120.7 (6)
C4C—N4C—H44C	109.00	C3D—C4D—C5D	122.0 (4)
H42C—N4C—H44C	109.00	N4D—C4D—C5D	118.1 (3)
H43C—N4C—H44C	112.00	N4D—C4D—C3D	119.9 (3)
C4C—N4C—H42C	111.00	N4D—C4D—C3F	121.9 (3)
C4C—N4C—H43C	113.00	C4D—C5D—C6F	111.5 (5)
N11D—N1D—C1D	113.9 (3)	C4D—C5D—C6D	119.2 (5)
N1D—N11D—C11D	113.7 (3)	C4D—C5F—C6F	118.9 (6)
H42D—N4D—H44D	107.00	C1D—C6D—C5D	120.5 (5)
C4D—N4D—H44D	111.00	C1D—C6F—C5F	118.9 (5)
C4D—N4D—H42D	109.00	N11D—C11D—C61D	116.3 (4)
C4D—N4D—H43D	112.00	C21F—C11D—C61F	120.8 (5)
H43D—N4D—H44D	107.00	N11D—C11D—C21D	123.8 (3)
H42D—N4D—H43D	110.00	N11D—C11D—C21F	123.9 (4)
N1C—C1C—C2E	116.7 (4)	C21D—C11D—C61D	120.0 (4)
N1C—C1C—C6C	122.6 (4)	C11D—C21D—C31D	119.5 (4)
N1C—C1C—C2C	116.8 (4)	C11D—C21F—C31F	119.0 (6)
C2E—C1C—C6E	119.8 (4)	C21D—C31D—C41D	120.0 (6)
N1C—C1C—C6E	123.5 (4)	C21F—C31F—C41D	122.0 (6)
C2C—C1C—C6E	114.7 (5)	C31D—C41D—C51D	120.8 (5)
C2E—C1C—C6C	115.5 (5)	C41D—C51F—C61F	120.1 (6)
C2C—C1C—C6C	120.6 (5)	C11D—C61D—C51D	120.4 (7)
C1C—C2C—C3E	114.1 (6)	C11D—C61F—C51F	119.1 (6)
C1C—C2C—C3C	120.5 (6)	C1D—C2D—H2D	120.00
C1C—C2E—C3C	113.4 (6)	C3D—C2D—H2D	120.00
C1C—C2E—C3E	120.0 (6)	C1D—C2F—H2F	120.00
C2C—C3C—C4C	118.8 (6)	C3F—C2F—H2F	120.00
C2E—C3E—C4C	118.3 (6)	C2D—C3D—H3D	120.00
N4C—C4C—C3C	121.0 (3)	C4D—C3D—H3D	120.00
N4C—C4C—C5C	117.3 (3)	C2F—C3F—H3F	120.00
N4C—C4C—C5E	117.6 (3)	C4D—C3F—H3F	120.00
C3E—C4C—C5E	123.0 (4)	C4D—C5D—H5D	120.00
C3E—C4C—C5C	117.6 (4)	C6D—C5D—H5D	120.00
N4C—C4C—C3E	119.4 (3)	C4D—C5F—H5F	121.00
C3C—C4C—C5E	116.6 (4)	C6F—C5F—H5F	121.00
C3C—C4C—C5C	121.7 (4)	C1D—C6D—H6D	120.00
C4C—C5C—C6E	111.0 (5)	C5D—C6D—H6D	120.00
C4C—C5C—C6C	119.0 (5)	C1D—C6F—H6F	121.00
C4C—C5E—C6E	119.1 (6)	C5F—C6F—H6F	121.00
C1C—C6C—C5C	119.4 (6)	C31D—C21D—H21D	120.00
C1C—C6E—C5E	119.7 (6)	C11D—C21D—H21D	120.00
C21E—C11C—C61E	120.5 (5)	C11D—C21F—H21F	121.00
N11C—C11C—C21E	124.0 (4)	C31F—C21F—H21F	120.00
C21E—C11C—C61C	114.6 (5)	C21D—C31D—H31D	120.00
C21C—C11C—C61C	121.2 (5)	C41D—C31D—H31D	120.00
C21C—C11C—C61E	114.5 (5)	C21F—C31F—H31F	119.00
N11C—C11C—C61E	115.5 (4)	C41D—C31F—H31F	119.00
N11C—C11C—C21C	124.3 (4)	C51D—C41D—H41D	120.00
N11C—C11C—C61C	114.5 (4)	C31D—C41D—H41D	120.00
C11C—C21C—C31C	119.2 (6)	C31F—C41D—H41D	121.00
C11C—C21E—C31E	119.8 (7)	C51F—C41D—H41D	120.00
C21C—C31C—C41C	121.2 (6)	C41D—C51D—H51D	120.00
C21E—C31E—C41C	120.2 (7)	C61D—C51D—H51D	120.00
C31E—C41C—C51E	120.9 (5)	C61F—C51F—H51F	120.00
C31C—C41C—C51C	119.8 (5)	C41D—C51F—H51F	120.00
C41C—C51C—C61C	119.6 (6)	C51D—C61D—H61D	120.00
C41C—C51E—C61E	119.7 (7)	C11D—C61D—H61D	120.00
C41C—C51E—C61C	109.1 (6)	C11D—C61F—H61F	121.00
C11C—C61C—C51C	118.9 (6)	C51F—C61F—H61F	120.00
C1C—C2C—H2C	120.00	O11A—C1A—C2A	115.3 (2)
C3C—C2C—H2C	120.00	O11A—C1A—O12A	126.7 (3)
C1C—C2E—H2E	120.00	O12A—C1A—C2A	118.0 (2)
C3E—C2E—H2E	120.00	C1A—C2A—C3A	111.04 (19)
C2C—C3C—H3C	121.00	O2A—C2A—C3A	109.2 (2)
C4C—C3C—H3C	121.00	O2A—C2A—C1A	110.0 (2)
C4C—C3E—H3E	121.00	C2A—C3A—C4A	111.85 (19)
C2E—C3E—H3E	121.00	O3A—C3A—C4A	110.7 (2)
C6C—C5C—H5C	120.00	O3A—C3A—C2A	108.1 (2)
C4C—C5C—H5E	103.00	O41A—C4A—O42A	125.0 (3)
C4C—C5C—H5C	121.00	O42A—C4A—C3A	122.0 (2)
C4C—C5E—H5E	120.00	O41A—C4A—C3A	113.0 (2)
C6E—C5E—H5E	121.00	O2A—C2A—H2A	109.00
C1C—C6C—H6C	120.00	C1A—C2A—H2A	109.00
C5C—C6C—H6C	120.00	C3A—C2A—H2A	109.00
C1C—C6E—H6E	120.00	C4A—C3A—H3A	109.00
C5E—C6E—H6E	120.00	O3A—C3A—H3A	109.00
C31C—C21C—H21C	120.00	C2A—C3A—H3A	109.00
C11C—C21C—H21C	120.00	O11B—C1B—C2B	117.8 (2)
C31E—C21E—H21E	120.00	O11B—C1B—O12B	126.3 (3)
C11C—C21E—H21E	120.00	O12B—C1B—C2B	115.8 (3)
C41C—C31C—H31C	119.00	O2B—C2B—C1B	110.1 (2)
C21E—C31E—H31E	120.00	O2B—C2B—C3B	109.38 (19)
C41C—C31E—H31E	120.00	C1B—C2B—C3B	110.5 (2)
C51E—C41C—H41C	118.00	C2B—C3B—C4B	106.4 (2)
C51C—C41C—H41C	120.00	O3B—C3B—C2B	111.8 (2)
C31E—C41C—H41C	121.00	O3B—C3B—C4B	114.4 (2)
C31C—C41C—H41C	120.00	O41B—C4B—O42B	124.6 (3)
C41C—C51C—H51C	120.00	O41B—C4B—C3B	114.4 (2)
C61C—C51C—H51C	120.00	O42B—C4B—C3B	120.8 (2)
C41C—C51E—H51E	120.00	O2B—C2B—H2B	109.00
C61E—C51E—H51E	120.00	C1B—C2B—H2B	109.00
C11C—C61C—H61C	121.00	C3B—C2B—H2B	109.00
C51C—C61C—H61E	109.00	O3B—C3B—H3B	108.00
C51C—C61C—H61C	121.00	C2B—C3B—H3B	108.00
C11C—C61E—H61E	121.00	C4B—C3B—H3B	108.00
C51E—C61E—H61E	121.00
C1C—N1C—N11C—C11C	−178.6 (2)	N4D—C4D—C5D—C6D	179.2 (5)
N11C—N1C—C1C—C2C	−164.5 (4)	C3D—C4D—C5D—C6D	−3.5 (8)
N11C—N1C—C1C—C6C	17.2 (5)	C4D—C5D—C6D—C1D	−1.7 (9)
N1C—N11C—C11C—C21C	10.7 (6)	N11D—C11D—C21D—C31D	177.5 (5)
N1C—N11C—C11C—C61C	−166.6 (4)	C61D—C11D—C21D—C31D	−2.0 (7)
C1D—N1D—N11D—C11D	180.0 (2)	N11D—C11D—C61D—C51D	−178.6 (6)
N11D—N1D—C1D—C2D	6.4 (5)	C21D—C11D—C61D—C51D	0.9 (9)
N11D—N1D—C1D—C6D	−169.0 (4)	C11D—C21D—C31D—C41D	2.3 (9)
N1D—N11D—C11D—C61D	−160.8 (4)	C21D—C31D—C41D—C51D	−1.7 (10)
N1D—N11D—C11D—C21D	19.7 (4)	C31D—C41D—C51D—C61D	0.6 (10)
C6C—C1C—C2C—C3C	0.6 (9)	C41D—C51D—C61D—C11D	−0.3 (11)
N1C—C1C—C6C—C5C	177.4 (5)	O11A—C1A—C2A—O2A	−17.3 (3)
N1C—C1C—C2C—C3C	−177.7 (6)	O11A—C1A—C2A—C3A	−138.4 (2)
C2C—C1C—C6C—C5C	−0.8 (9)	O12A—C1A—C2A—O2A	165.0 (2)
C1C—C2C—C3C—C4C	−0.9 (10)	O12A—C1A—C2A—C3A	44.0 (3)
C2C—C3C—C4C—N4C	179.9 (5)	O2A—C2A—C3A—O3A	−71.7 (2)
C2C—C3C—C4C—C5C	1.5 (9)	O2A—C2A—C3A—C4A	50.5 (3)
N4C—C4C—C5C—C6C	179.9 (5)	C1A—C2A—C3A—O3A	49.9 (3)
C3C—C4C—C5C—C6C	−1.7 (9)	C1A—C2A—C3A—C4A	172.0 (2)
C4C—C5C—C6C—C1C	1.3 (9)	O3A—C3A—C4A—O41A	164.6 (2)
N11C—C11C—C21C—C31C	177.4 (5)	O3A—C3A—C4A—O42A	−18.0 (4)
N11C—C11C—C61C—C51C	−178.1 (5)	C2A—C3A—C4A—O41A	44.0 (3)
C21C—C11C—C61C—C51C	4.5 (9)	C2A—C3A—C4A—O42A	−138.6 (3)
C61C—C11C—C21C—C31C	−5.5 (9)	O11B—C1B—C2B—O2B	0.5 (3)
C11C—C21C—C31C—C41C	2.4 (11)	O11B—C1B—C2B—C3B	−120.4 (3)
C21C—C31C—C41C—C51C	1.5 (10)	O12B—C1B—C2B—O2B	−178.8 (2)
C31C—C41C—C51C—C61C	−2.5 (9)	O12B—C1B—C2B—C3B	60.3 (3)
C41C—C51C—C61C—C11C	−0.5 (10)	O2B—C2B—C3B—O3B	−61.9 (2)
N1D—C1D—C2D—C3D	178.2 (5)	O2B—C2B—C3B—C4B	63.7 (3)
C6D—C1D—C2D—C3D	−6.4 (8)	C1B—C2B—C3B—O3B	59.5 (3)
N1D—C1D—C6D—C5D	−177.8 (5)	C1B—C2B—C3B—C4B	−174.9 (2)
C2D—C1D—C6D—C5D	6.5 (8)	O3B—C3B—C4B—O41B	19.5 (3)
C1D—C2D—C3D—C4D	1.5 (9)	O3B—C3B—C4B—O42B	−164.8 (2)
C2D—C3D—C4D—N4D	−179.2 (5)	C2B—C3B—C4B—O41B	−104.6 (3)
C2D—C3D—C4D—C5D	3.6 (8)	C2B—C3B—C4B—O42B	71.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2A—H21A···O11A	0.77	2.11	2.601 (3)	122
O2B—H21B···O11B	0.77	2.09	2.599 (3)	124
O2B—H21B···O42B^i	0.77	2.21	2.754 (3)	129
O3A—H31A···O11A^ii	0.80	2.07	2.872 (3)	178
O3B—H31B···O12A^iii	0.80	2.08	2.881 (3)	180
O41A—H41A···O12A^iii	0.78	1.83	2.602 (3)	170
O41B—H41B···O12B^iii	0.80	1.73	2.531 (3)	176
N4C—H42C···O2B^iv	0.95	1.87	2.779 (3)	158
N4C—H43C···O11B	0.85	1.91	2.724 (3)	162
N4C—H44C···O12B^i	0.89	1.91	2.785 (3)	168
N4D—H42D···O2A^ii	0.88	1.95	2.814 (3)	169
N4D—H43D···O3B	0.92	2.30	2.898 (3)	122
N4D—H43D···O42A	0.92	2.39	2.847 (3)	111
N4D—H44D···O11A^v	0.82	1.98	2.781 (3)	167
C3A—H3A···O41B^iv	1.00	2.37	3.167 (3)	137
C3B—H3B···O41A^ii	1.00	2.48	3.184 (3)	127

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) x, y−1, z; (iv) x, y+1, z; (v) x+1, y−1, z.