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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270110020597/fg3168sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270110020597/fg3168Isup2.hkl
Contains datablock I

CCDC reference: 786812

Computing details top

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 top
Crystal data top
C12H12N3+·C4H5O6Z = 2
Mr = 347.33F(000) = 364
Triclinic, P1Dx = 1.456 Mg m3
Hall symbol: P 1Melting point: 467 K
a = 6.1710 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.4134 (3) ÅCell parameters from 7191 reflections
c = 18.2438 (6) Åθ = 2.9–32.2°
α = 91.754 (3)°µ = 0.11 mm1
β = 91.308 (3)°T = 200 K
γ = 108.135 (4)°Plate, orange-red
V = 792.33 (6) Å30.30 × 0.20 × 0.15 mm
Data collection top
Oxford Gemini-S CCD detector
diffractometer
4174 independent reflections
Radiation source: Enhance (Mo) X-ray source3593 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
ω scansθmax = 29.0°, θmin = 2.9°
Absorption correction: multi-scan
SADABS (Sheldrick, 1996)
h = 88
Tmin = 0.874, Tmax = 0.980k = 1010
16695 measured reflectionsl = 2424
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters not refined
S = 1.01 w = 1/[σ2(Fo2) + (0.0802P)2]
where P = (Fo2 + 2Fc2)/3
4174 reflections(Δ/σ)max < 0.001
432 parametersΔρmax = 0.43 e Å3
3 restraintsΔρmin = 0.31 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
N1C0.0628 (5)0.5384 (4)0.08229 (15)0.0322 (8)
N4C0.1760 (4)0.5383 (3)0.38852 (12)0.0195 (6)
N11C0.1379 (5)0.5723 (4)0.06254 (15)0.0347 (8)
C1C0.0825 (5)0.5374 (4)0.16033 (17)0.0272 (8)
C2C0.2964 (11)0.4571 (11)0.1863 (4)0.0281 (14)*0.500
C2E0.2957 (11)0.5296 (11)0.1872 (4)0.0280 (14)*0.500
C3C0.3319 (11)0.4563 (11)0.2614 (3)0.0246 (13)*0.500
C3E0.3281 (11)0.5288 (10)0.2630 (3)0.0248 (13)*0.500
C4C0.1479 (4)0.5351 (3)0.30893 (15)0.0203 (7)
C5C0.0709 (10)0.6190 (10)0.2837 (3)0.0249 (12)*0.500
C5E0.0633 (11)0.5398 (10)0.2840 (3)0.0261 (12)*0.500
C6C0.1044 (11)0.6185 (10)0.2089 (3)0.0257 (12)*0.500
C6E0.0963 (11)0.5392 (10)0.2092 (3)0.0253 (12)*0.500
C11C0.1642 (5)0.5787 (4)0.01519 (16)0.0286 (9)
C21C0.0058 (11)0.5805 (11)0.0652 (3)0.0272 (13)*0.500
C21E0.0111 (12)0.5046 (11)0.0658 (4)0.0306 (14)*0.500
C31C0.0419 (12)0.5946 (11)0.1387 (4)0.0290 (13)*0.500
C31E0.0316 (13)0.5164 (12)0.1397 (4)0.0367 (16)*0.500
C41C0.2509 (6)0.5998 (5)0.16274 (18)0.0369 (10)
C51C0.4195 (12)0.5862 (10)0.1126 (4)0.0320 (13)*0.500
C51E0.4278 (13)0.6804 (12)0.1130 (4)0.0380 (15)*0.500
C61C0.3743 (11)0.5748 (10)0.0377 (4)0.0307 (13)*0.500
C61E0.3888 (13)0.6694 (12)0.0382 (4)0.0384 (15)*0.500
N1D0.1669 (5)0.0823 (4)1.00283 (14)0.0313 (8)
N4D0.3820 (4)0.1221 (3)0.70360 (12)0.0198 (6)
N11D0.0375 (5)0.0488 (4)1.01770 (15)0.0329 (8)
C1D0.2072 (5)0.0879 (4)0.92596 (16)0.0262 (8)
C2D0.0388 (10)0.0771 (10)0.8706 (3)0.0209 (12)*0.500
C2F0.0402 (11)0.0105 (11)0.8723 (3)0.0235 (13)*0.500
C3D0.0959 (10)0.0889 (9)0.7979 (3)0.0186 (11)*0.500
C3F0.0972 (11)0.0211 (10)0.7994 (3)0.0236 (13)*0.500
C4D0.3178 (4)0.1069 (4)0.77999 (15)0.0196 (7)
C5D0.4805 (10)0.1031 (9)0.8320 (3)0.0246 (12)*0.500
C5F0.4912 (10)0.1944 (10)0.8347 (3)0.0254 (12)*0.500
C6D0.4246 (10)0.0911 (9)0.9050 (3)0.0248 (12)*0.500
C6F0.4348 (10)0.1835 (10)0.9080 (3)0.0261 (12)*0.500
C11D0.0770 (5)0.0432 (4)1.09485 (16)0.0280 (8)
C21D0.0920 (6)0.1248 (5)1.14872 (16)0.0329 (14)*0.500
C21F0.0835 (11)0.0406 (9)1.1472 (3)0.0300 (13)*0.500
C31D0.0351 (12)0.1183 (12)1.2218 (4)0.0366 (15)*0.500
C31F0.0244 (12)0.0279 (11)1.2198 (4)0.0331 (14)*0.500
C41D0.1885 (6)0.0245 (5)1.24124 (16)0.0390 (10)
C51D0.3557 (13)0.0581 (12)1.1884 (4)0.0390 (15)*0.500
C51F0.3483 (12)0.0325 (11)1.1886 (4)0.0333 (14)*0.500
C61D0.3000 (12)0.0492 (11)1.1149 (4)0.0347 (14)*0.500
C61F0.2934 (11)0.0419 (10)1.1142 (4)0.0301 (13)*0.500
O2A0.3622 (3)0.5088 (3)0.69950 (11)0.0228 (5)
O3A0.1018 (3)0.7150 (3)0.66547 (12)0.0276 (6)
O11A0.4098 (3)0.8420 (3)0.68346 (12)0.0260 (6)
O12A0.1931 (3)0.9075 (3)0.58533 (11)0.0258 (6)
O41A0.2114 (3)0.2534 (3)0.59407 (12)0.0249 (6)
O42A0.1255 (4)0.3572 (3)0.65412 (15)0.0391 (8)
C1A0.2955 (4)0.8008 (4)0.63381 (14)0.0179 (7)
C2A0.2911 (4)0.5935 (3)0.63153 (14)0.0176 (7)
C3A0.0536 (4)0.5847 (3)0.61653 (15)0.0178 (7)
C4A0.0376 (4)0.3851 (4)0.62462 (14)0.0187 (7)
O2B0.0297 (3)0.0729 (3)0.41205 (12)0.0250 (6)
O3B0.2806 (3)0.0322 (3)0.54840 (10)0.0231 (5)
O11B0.0018 (3)0.2667 (3)0.43520 (13)0.0280 (6)
O12B0.3787 (3)0.4087 (3)0.43645 (13)0.0288 (6)
O41B0.3136 (3)0.2980 (3)0.49378 (12)0.0263 (6)
O42B0.5627 (3)0.1540 (3)0.41079 (11)0.0235 (6)
C1B0.2011 (5)0.2653 (4)0.43131 (15)0.0195 (7)
C2B0.2408 (4)0.0740 (3)0.41817 (14)0.0173 (7)
C3B0.3850 (4)0.0350 (3)0.48092 (14)0.0164 (7)
C4B0.4333 (4)0.1496 (4)0.45930 (15)0.0174 (7)
H2C0.421400.401700.152800.0340*0.500
H2E0.418500.525000.154000.0340*0.500
H3C0.480300.402300.279500.0300*0.500
H3E0.471800.523900.281900.0300*0.500
H5C0.195100.675600.317300.0300*0.500
H5E0.184300.543400.317800.0310*0.500
H6C0.252700.672600.190700.0310*0.500
H6E0.239800.539900.191100.0300*0.500
H21C0.154000.572000.049300.0330*0.500
H21E0.161500.445200.050000.0370*0.500
H31C0.073100.600800.173200.0350*0.500
H31E0.090200.467100.174900.0440*0.500
H41C0.282300.612700.213400.0440*
H42C0.104200.662800.409400.0230*
H43C0.107200.471800.410600.0230*
H44C0.324200.502800.397700.0230*
H51C0.563700.584600.129200.0380*0.500
H51E0.576100.743400.129600.0460*0.500
H61C0.486600.564600.003000.0370*0.500
H61E0.510400.721600.003200.0460*0.500
H2D0.114000.061800.883500.0250*0.500
H2F0.112900.049700.885300.0280*0.500
H3D0.015700.084700.760600.0220*0.500
H3F0.017700.031700.762400.0280*0.500
H5D0.629700.108800.818000.0300*0.500
H5F0.642500.258900.821100.0310*0.500
H6D0.534900.084900.941200.0300*0.500
H6F0.547200.239300.945500.0310*0.500
H21D0.244800.184901.135400.0400*0.500
H21F0.233600.047301.133900.0360*0.500
H31D0.148000.177601.258700.0440*0.500
H31F0.134400.021401.256100.0400*0.500
H41D0.225500.017601.291600.0470*
H42D0.469200.238800.697100.0240*
H43D0.257200.090800.672100.0240*
H44D0.457200.051800.693100.0240*
H51D0.507600.120501.202000.0470*0.500
H51F0.495900.031701.202600.0400*0.500
H61D0.414400.106401.078100.0420*0.500
H61F0.403200.047301.077700.0360*0.500
H2A0.398800.520200.591500.0210*
H3A0.015600.624000.565200.0210*
H41A0.20600.150400.596900.0300*
H21A0.359900.594400.724700.0270*
H31A0.237600.748200.670200.0330*
H2B0.323000.076500.371400.0210*
H3B0.533700.139800.483900.0200*
H21B0.063200.026300.419800.0300*
H31B0.149200.002600.558700.0280*
H41B0.328500.392000.474700.0320*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1C0.0307 (13)0.0394 (15)0.0258 (13)0.0100 (11)0.0020 (10)0.0007 (10)
N4C0.0145 (10)0.0191 (10)0.0258 (12)0.0065 (8)0.0014 (8)0.0005 (8)
N11C0.0296 (13)0.0492 (17)0.0259 (13)0.0133 (12)0.0021 (11)0.0017 (12)
C1C0.0250 (14)0.0276 (14)0.0291 (15)0.0087 (11)0.0007 (12)0.0008 (11)
C4C0.0211 (13)0.0148 (11)0.0249 (13)0.0055 (10)0.0029 (10)0.0005 (9)
C11C0.0299 (15)0.0303 (15)0.0260 (15)0.0101 (12)0.0011 (12)0.0008 (12)
C41C0.0434 (19)0.0467 (19)0.0258 (16)0.0208 (16)0.0063 (14)0.0058 (14)
N1D0.0300 (13)0.0437 (15)0.0207 (12)0.0117 (12)0.0036 (10)0.0052 (10)
N4D0.0182 (10)0.0223 (11)0.0211 (11)0.0093 (8)0.0033 (9)0.0028 (8)
N11D0.0302 (13)0.0429 (15)0.0253 (13)0.0107 (12)0.0046 (10)0.0030 (11)
C1D0.0260 (14)0.0319 (15)0.0211 (14)0.0094 (12)0.0042 (11)0.0031 (11)
C4D0.0202 (12)0.0205 (12)0.0194 (12)0.0081 (10)0.0018 (10)0.0002 (10)
C11D0.0312 (15)0.0302 (15)0.0215 (14)0.0078 (12)0.0019 (11)0.0018 (11)
C41D0.054 (2)0.0444 (19)0.0234 (15)0.0210 (17)0.0122 (15)0.0065 (13)
O2A0.0203 (9)0.0205 (9)0.0296 (10)0.0084 (7)0.0094 (8)0.0057 (7)
O3A0.0127 (8)0.0202 (9)0.0470 (13)0.0019 (7)0.0048 (8)0.0036 (8)
O11A0.0270 (10)0.0234 (10)0.0322 (11)0.0136 (8)0.0113 (8)0.0027 (8)
O12A0.0263 (10)0.0216 (9)0.0334 (11)0.0122 (8)0.0080 (8)0.0073 (8)
O41A0.0212 (9)0.0178 (9)0.0372 (11)0.0089 (7)0.0050 (8)0.0015 (8)
O42A0.0288 (11)0.0310 (12)0.0620 (16)0.0180 (10)0.0176 (11)0.0047 (10)
C1A0.0118 (10)0.0194 (12)0.0242 (13)0.0075 (9)0.0020 (10)0.0013 (10)
C2A0.0125 (11)0.0182 (12)0.0228 (13)0.0057 (9)0.0006 (9)0.0018 (10)
C3A0.0128 (11)0.0178 (11)0.0237 (13)0.0058 (9)0.0027 (9)0.0015 (9)
C4A0.0169 (11)0.0242 (12)0.0174 (12)0.0093 (10)0.0046 (9)0.0025 (9)
O2B0.0157 (9)0.0170 (9)0.0419 (12)0.0053 (7)0.0058 (8)0.0037 (8)
O3B0.0220 (9)0.0284 (10)0.0191 (9)0.0083 (8)0.0035 (7)0.0014 (7)
O11B0.0181 (9)0.0220 (10)0.0464 (13)0.0094 (8)0.0032 (9)0.0059 (9)
O12B0.0202 (9)0.0152 (9)0.0514 (13)0.0051 (7)0.0106 (9)0.0030 (8)
O41B0.0252 (10)0.0168 (9)0.0385 (12)0.0077 (8)0.0132 (9)0.0035 (8)
O42B0.0187 (9)0.0215 (9)0.0316 (11)0.0077 (7)0.0083 (8)0.0024 (8)
C1B0.0236 (13)0.0154 (11)0.0221 (13)0.0089 (10)0.0080 (10)0.0052 (9)
C2B0.0145 (11)0.0168 (11)0.0211 (12)0.0053 (9)0.0033 (9)0.0013 (9)
C3B0.0135 (11)0.0151 (11)0.0200 (12)0.0040 (9)0.0007 (9)0.0008 (9)
C4B0.0111 (10)0.0184 (11)0.0227 (13)0.0047 (9)0.0003 (9)0.0002 (9)
Geometric parameters (Å, º) top
O2A—C2A1.423 (3)C6C—H6C0.9500
O3A—C3A1.408 (3)C6E—H6E0.9500
O11A—C1A1.248 (3)C21C—H21C0.9500
O12A—C1A1.251 (3)C21E—H21E0.9500
O41A—C4A1.305 (3)C31C—H31C0.9500
O42A—C4A1.207 (4)C31E—H31E0.9500
O2A—H21A0.7700C41C—H41C0.9500
O3A—H31A0.8000C51C—H51C0.9500
O41A—H41A0.7800C51E—H51E0.9500
O2B—C2B1.414 (3)C61C—H61C0.9500
O3B—C3B1.400 (3)C61E—H61E0.9500
O11B—C1B1.237 (4)C1D—C2F1.379 (7)
O12B—C1B1.267 (4)C1D—C2D1.415 (7)
O41B—C4B1.307 (3)C1D—C6F1.414 (7)
O42B—C4B1.212 (3)C1D—C6D1.397 (7)
O2B—H21B0.7700C2D—C3D1.379 (8)
O3B—H31B0.8000C2F—C3F1.382 (8)
O41B—H41B0.8000C3D—C4D1.382 (7)
N1C—C1C1.432 (4)C3F—C4D1.371 (8)
N1C—N11C1.249 (4)C4D—C5F1.429 (7)
N4C—C4C1.467 (4)C4D—C5D1.373 (7)
N11C—C11C1.432 (4)C5D—C6D1.382 (8)
N4C—H44C0.8900C5F—C6F1.388 (8)
N4C—H43C0.8500C11D—C61F1.386 (8)
N4C—H42C0.9500C11D—C21F1.365 (7)
N1D—C1D1.430 (4)C11D—C61D1.396 (8)
N1D—N11D1.245 (4)C11D—C21D1.394 (5)
N4D—C4D1.456 (4)C21D—C31D1.385 (8)
N11D—C11D1.434 (4)C21F—C31F1.380 (9)
N4D—H42D0.8800C31D—C41D1.398 (9)
N4D—H44D0.8200C31F—C41D1.372 (9)
N4D—H43D0.9200C41D—C51F1.377 (8)
C1C—C6E1.399 (7)C41D—C51D1.376 (9)
C1C—C2C1.370 (8)C51D—C61D1.390 (10)
C1C—C2E1.399 (8)C51F—C61F1.405 (10)
C1C—C6C1.402 (7)C2D—H2D0.9500
C2C—C3C1.392 (9)C2F—H2F0.9500
C2E—C3E1.402 (9)C3D—H3D0.9500
C3C—C4C1.376 (7)C3F—H3F0.9500
C3E—C4C1.365 (7)C5D—H5D0.9500
C4C—C5E1.381 (7)C5F—H5F0.9500
C4C—C5C1.395 (7)C6D—H6D0.9500
C5C—C6C1.385 (8)C6F—H6F0.9500
C5E—C6E1.384 (8)C21D—H21D0.9500
C11C—C61E1.419 (9)C21F—H21F0.9500
C11C—C21C1.378 (7)C31D—H31D0.9500
C11C—C61C1.378 (8)C31F—H31F0.9500
C11C—C21E1.370 (8)C41D—H41D0.9500
C21C—C31C1.380 (9)C51D—H51D0.9500
C21E—C31E1.380 (10)C51F—H51F0.9500
C31C—C41C1.361 (9)C61D—H61D0.9500
C31E—C41C1.383 (9)C61F—H61F0.9500
C41C—C51E1.374 (9)C1A—C2A1.545 (4)
C41C—C51C1.399 (8)C2A—C3A1.518 (4)
C51C—C61C1.401 (10)C3A—C4A1.525 (4)
C51E—C61E1.392 (10)C2A—H2A1.0000
C2C—H2C0.9500C3A—H3A1.0000
C2E—H2E0.9500C1B—C2B1.525 (4)
C3C—H3C0.9500C2B—C3B1.523 (4)
C3E—H3E0.9500C3B—C4B1.531 (4)
C5C—H5C0.9500C2B—H2B1.0000
C5E—H5E0.9500C3B—H3B1.0000
C2A—O2A—H21A103.00N1D—C1D—C2D124.5 (4)
C3A—O3A—H31A133.00N1D—C1D—C2F123.9 (4)
C4A—O41A—H41A115.00C2D—C1D—C6D118.6 (4)
C2B—O2B—H21B107.00N1D—C1D—C6D116.7 (3)
C3B—O3B—H31B131.00C2F—C1D—C6F121.4 (4)
C4B—O41B—H41B109.00C1D—C2D—C3D120.2 (6)
N11C—N1C—C1C113.2 (3)C1D—C2F—C3F119.5 (6)
N1C—N11C—C11C114.7 (3)C2D—C3D—C4D119.1 (5)
H42C—N4C—H43C103.00C2F—C3F—C4D120.7 (6)
C4C—N4C—H44C109.00C3D—C4D—C5D122.0 (4)
H42C—N4C—H44C109.00N4D—C4D—C5D118.1 (3)
H43C—N4C—H44C112.00N4D—C4D—C3D119.9 (3)
C4C—N4C—H42C111.00N4D—C4D—C3F121.9 (3)
C4C—N4C—H43C113.00C4D—C5D—C6F111.5 (5)
N11D—N1D—C1D113.9 (3)C4D—C5D—C6D119.2 (5)
N1D—N11D—C11D113.7 (3)C4D—C5F—C6F118.9 (6)
H42D—N4D—H44D107.00C1D—C6D—C5D120.5 (5)
C4D—N4D—H44D111.00C1D—C6F—C5F118.9 (5)
C4D—N4D—H42D109.00N11D—C11D—C61D116.3 (4)
C4D—N4D—H43D112.00C21F—C11D—C61F120.8 (5)
H43D—N4D—H44D107.00N11D—C11D—C21D123.8 (3)
H42D—N4D—H43D110.00N11D—C11D—C21F123.9 (4)
N1C—C1C—C2E116.7 (4)C21D—C11D—C61D120.0 (4)
N1C—C1C—C6C122.6 (4)C11D—C21D—C31D119.5 (4)
N1C—C1C—C2C116.8 (4)C11D—C21F—C31F119.0 (6)
C2E—C1C—C6E119.8 (4)C21D—C31D—C41D120.0 (6)
N1C—C1C—C6E123.5 (4)C21F—C31F—C41D122.0 (6)
C2C—C1C—C6E114.7 (5)C31D—C41D—C51D120.8 (5)
C2E—C1C—C6C115.5 (5)C41D—C51F—C61F120.1 (6)
C2C—C1C—C6C120.6 (5)C11D—C61D—C51D120.4 (7)
C1C—C2C—C3E114.1 (6)C11D—C61F—C51F119.1 (6)
C1C—C2C—C3C120.5 (6)C1D—C2D—H2D120.00
C1C—C2E—C3C113.4 (6)C3D—C2D—H2D120.00
C1C—C2E—C3E120.0 (6)C1D—C2F—H2F120.00
C2C—C3C—C4C118.8 (6)C3F—C2F—H2F120.00
C2E—C3E—C4C118.3 (6)C2D—C3D—H3D120.00
N4C—C4C—C3C121.0 (3)C4D—C3D—H3D120.00
N4C—C4C—C5C117.3 (3)C2F—C3F—H3F120.00
N4C—C4C—C5E117.6 (3)C4D—C3F—H3F120.00
C3E—C4C—C5E123.0 (4)C4D—C5D—H5D120.00
C3E—C4C—C5C117.6 (4)C6D—C5D—H5D120.00
N4C—C4C—C3E119.4 (3)C4D—C5F—H5F121.00
C3C—C4C—C5E116.6 (4)C6F—C5F—H5F121.00
C3C—C4C—C5C121.7 (4)C1D—C6D—H6D120.00
C4C—C5C—C6E111.0 (5)C5D—C6D—H6D120.00
C4C—C5C—C6C119.0 (5)C1D—C6F—H6F121.00
C4C—C5E—C6E119.1 (6)C5F—C6F—H6F121.00
C1C—C6C—C5C119.4 (6)C31D—C21D—H21D120.00
C1C—C6E—C5E119.7 (6)C11D—C21D—H21D120.00
C21E—C11C—C61E120.5 (5)C11D—C21F—H21F121.00
N11C—C11C—C21E124.0 (4)C31F—C21F—H21F120.00
C21E—C11C—C61C114.6 (5)C21D—C31D—H31D120.00
C21C—C11C—C61C121.2 (5)C41D—C31D—H31D120.00
C21C—C11C—C61E114.5 (5)C21F—C31F—H31F119.00
N11C—C11C—C61E115.5 (4)C41D—C31F—H31F119.00
N11C—C11C—C21C124.3 (4)C51D—C41D—H41D120.00
N11C—C11C—C61C114.5 (4)C31D—C41D—H41D120.00
C11C—C21C—C31C119.2 (6)C31F—C41D—H41D121.00
C11C—C21E—C31E119.8 (7)C51F—C41D—H41D120.00
C21C—C31C—C41C121.2 (6)C41D—C51D—H51D120.00
C21E—C31E—C41C120.2 (7)C61D—C51D—H51D120.00
C31E—C41C—C51E120.9 (5)C61F—C51F—H51F120.00
C31C—C41C—C51C119.8 (5)C41D—C51F—H51F120.00
C41C—C51C—C61C119.6 (6)C51D—C61D—H61D120.00
C41C—C51E—C61E119.7 (7)C11D—C61D—H61D120.00
C41C—C51E—C61C109.1 (6)C11D—C61F—H61F121.00
C11C—C61C—C51C118.9 (6)C51F—C61F—H61F120.00
C1C—C2C—H2C120.00O11A—C1A—C2A115.3 (2)
C3C—C2C—H2C120.00O11A—C1A—O12A126.7 (3)
C1C—C2E—H2E120.00O12A—C1A—C2A118.0 (2)
C3E—C2E—H2E120.00C1A—C2A—C3A111.04 (19)
C2C—C3C—H3C121.00O2A—C2A—C3A109.2 (2)
C4C—C3C—H3C121.00O2A—C2A—C1A110.0 (2)
C4C—C3E—H3E121.00C2A—C3A—C4A111.85 (19)
C2E—C3E—H3E121.00O3A—C3A—C4A110.7 (2)
C6C—C5C—H5C120.00O3A—C3A—C2A108.1 (2)
C4C—C5C—H5E103.00O41A—C4A—O42A125.0 (3)
C4C—C5C—H5C121.00O42A—C4A—C3A122.0 (2)
C4C—C5E—H5E120.00O41A—C4A—C3A113.0 (2)
C6E—C5E—H5E121.00O2A—C2A—H2A109.00
C1C—C6C—H6C120.00C1A—C2A—H2A109.00
C5C—C6C—H6C120.00C3A—C2A—H2A109.00
C1C—C6E—H6E120.00C4A—C3A—H3A109.00
C5E—C6E—H6E120.00O3A—C3A—H3A109.00
C31C—C21C—H21C120.00C2A—C3A—H3A109.00
C11C—C21C—H21C120.00O11B—C1B—C2B117.8 (2)
C31E—C21E—H21E120.00O11B—C1B—O12B126.3 (3)
C11C—C21E—H21E120.00O12B—C1B—C2B115.8 (3)
C41C—C31C—H31C119.00O2B—C2B—C1B110.1 (2)
C21E—C31E—H31E120.00O2B—C2B—C3B109.38 (19)
C41C—C31E—H31E120.00C1B—C2B—C3B110.5 (2)
C51E—C41C—H41C118.00C2B—C3B—C4B106.4 (2)
C51C—C41C—H41C120.00O3B—C3B—C2B111.8 (2)
C31E—C41C—H41C121.00O3B—C3B—C4B114.4 (2)
C31C—C41C—H41C120.00O41B—C4B—O42B124.6 (3)
C41C—C51C—H51C120.00O41B—C4B—C3B114.4 (2)
C61C—C51C—H51C120.00O42B—C4B—C3B120.8 (2)
C41C—C51E—H51E120.00O2B—C2B—H2B109.00
C61E—C51E—H51E120.00C1B—C2B—H2B109.00
C11C—C61C—H61C121.00C3B—C2B—H2B109.00
C51C—C61C—H61E109.00O3B—C3B—H3B108.00
C51C—C61C—H61C121.00C2B—C3B—H3B108.00
C11C—C61E—H61E121.00C4B—C3B—H3B108.00
C51E—C61E—H61E121.00
C1C—N1C—N11C—C11C178.6 (2)N4D—C4D—C5D—C6D179.2 (5)
N11C—N1C—C1C—C2C164.5 (4)C3D—C4D—C5D—C6D3.5 (8)
N11C—N1C—C1C—C6C17.2 (5)C4D—C5D—C6D—C1D1.7 (9)
N1C—N11C—C11C—C21C10.7 (6)N11D—C11D—C21D—C31D177.5 (5)
N1C—N11C—C11C—C61C166.6 (4)C61D—C11D—C21D—C31D2.0 (7)
C1D—N1D—N11D—C11D180.0 (2)N11D—C11D—C61D—C51D178.6 (6)
N11D—N1D—C1D—C2D6.4 (5)C21D—C11D—C61D—C51D0.9 (9)
N11D—N1D—C1D—C6D169.0 (4)C11D—C21D—C31D—C41D2.3 (9)
N1D—N11D—C11D—C61D160.8 (4)C21D—C31D—C41D—C51D1.7 (10)
N1D—N11D—C11D—C21D19.7 (4)C31D—C41D—C51D—C61D0.6 (10)
C6C—C1C—C2C—C3C0.6 (9)C41D—C51D—C61D—C11D0.3 (11)
N1C—C1C—C6C—C5C177.4 (5)O11A—C1A—C2A—O2A17.3 (3)
N1C—C1C—C2C—C3C177.7 (6)O11A—C1A—C2A—C3A138.4 (2)
C2C—C1C—C6C—C5C0.8 (9)O12A—C1A—C2A—O2A165.0 (2)
C1C—C2C—C3C—C4C0.9 (10)O12A—C1A—C2A—C3A44.0 (3)
C2C—C3C—C4C—N4C179.9 (5)O2A—C2A—C3A—O3A71.7 (2)
C2C—C3C—C4C—C5C1.5 (9)O2A—C2A—C3A—C4A50.5 (3)
N4C—C4C—C5C—C6C179.9 (5)C1A—C2A—C3A—O3A49.9 (3)
C3C—C4C—C5C—C6C1.7 (9)C1A—C2A—C3A—C4A172.0 (2)
C4C—C5C—C6C—C1C1.3 (9)O3A—C3A—C4A—O41A164.6 (2)
N11C—C11C—C21C—C31C177.4 (5)O3A—C3A—C4A—O42A18.0 (4)
N11C—C11C—C61C—C51C178.1 (5)C2A—C3A—C4A—O41A44.0 (3)
C21C—C11C—C61C—C51C4.5 (9)C2A—C3A—C4A—O42A138.6 (3)
C61C—C11C—C21C—C31C5.5 (9)O11B—C1B—C2B—O2B0.5 (3)
C11C—C21C—C31C—C41C2.4 (11)O11B—C1B—C2B—C3B120.4 (3)
C21C—C31C—C41C—C51C1.5 (10)O12B—C1B—C2B—O2B178.8 (2)
C31C—C41C—C51C—C61C2.5 (9)O12B—C1B—C2B—C3B60.3 (3)
C41C—C51C—C61C—C11C0.5 (10)O2B—C2B—C3B—O3B61.9 (2)
N1D—C1D—C2D—C3D178.2 (5)O2B—C2B—C3B—C4B63.7 (3)
C6D—C1D—C2D—C3D6.4 (8)C1B—C2B—C3B—O3B59.5 (3)
N1D—C1D—C6D—C5D177.8 (5)C1B—C2B—C3B—C4B174.9 (2)
C2D—C1D—C6D—C5D6.5 (8)O3B—C3B—C4B—O41B19.5 (3)
C1D—C2D—C3D—C4D1.5 (9)O3B—C3B—C4B—O42B164.8 (2)
C2D—C3D—C4D—N4D179.2 (5)C2B—C3B—C4B—O41B104.6 (3)
C2D—C3D—C4D—C5D3.6 (8)C2B—C3B—C4B—O42B71.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2A—H21A···O11A0.772.112.601 (3)122
O2B—H21B···O11B0.772.092.599 (3)124
O2B—H21B···O42Bi0.772.212.754 (3)129
O3A—H31A···O11Aii0.802.072.872 (3)178
O3B—H31B···O12Aiii0.802.082.881 (3)180
O41A—H41A···O12Aiii0.781.832.602 (3)170
O41B—H41B···O12Biii0.801.732.531 (3)176
N4C—H42C···O2Biv0.951.872.779 (3)158
N4C—H43C···O11B0.851.912.724 (3)162
N4C—H44C···O12Bi0.891.912.785 (3)168
N4D—H42D···O2Aii0.881.952.814 (3)169
N4D—H43D···O3B0.922.302.898 (3)122
N4D—H43D···O42A0.922.392.847 (3)111
N4D—H44D···O11Av0.821.982.781 (3)167
C3A—H3A···O41Biv1.002.373.167 (3)137
C3B—H3B···O41Aii1.002.483.184 (3)127
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z; (iii) x, y1, z; (iv) x, y+1, z; (v) x+1, y1, z.
 

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