2-((E)-{2-[(1E)-(2,4-Dihydroxy-benzyl-idene)amino]phen-yl}iminiometh-yl)-5-hydroxy-phenolate methanol solvate.

The asymmetric unit of the title compound, C(20)H(16)N(2)O(4)·CH(3)OH, contains two Schiff base zwitterions and two methanol solvent mol-ecules. The dihedral angles between the central benzene ring and the two outer benzene rings of the Schiff base are 2.57 (7) and 52.30 (7)° in one mol-ecule and 5.83 (7) and 49.82 (7)° in the other mol-ecule. Intra-molecular O-H⋯N and N-H⋯O hydrogen bonds generate S(6) ring motifs, whereas intra-molecular N-H⋯N hydrogen bonds generate S(5) ring motifs. In the crystal structure, O-H⋯O, hydrogen bonds and weak C-H⋯O inter-actions link the mol-ecules into one-dimensional chains along the b-axis direction and are further connected by O-H⋯O and weak C-H⋯O inter-actions into a three-dimensional network. C-H⋯π and π-π inter-actions [centroid-centroid distances = 3.6228 (9) and 3.6881 (9) Å] are also observed in the crystal structure.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see, for example: Eltayeb et al. (2007a ▶,b ▶). For background to applications of Schiff base ligands, see, for example: Dao et al. (2000 ▶); Eltayeb & Ahmed (2005a ▶,b ▶); Fakhari et al. (2005 ▶); Karthikeyan et al. (2006 ▶); Sriram et al. (2006 ▶).

Experimental

Crystal data

C20H16N2O4·CH4O

M = 380.39

Triclinic,

a = 8.3672 (2) Å

b = 11.0813 (2) Å

c = 20.3217 (3) Å

α = 89.313 (1)°

β = 80.309 (1)°

γ = 79.641 (1)°

V = 1826.73 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100.0 (1) K

0.50 × 0.34 × 0.17 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.952, T max = 0.984

42593 measured reflections

10651 independent reflections

7203 reflections with I > 2σ(I)’

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.162

S = 1.05

10651 reflections

515 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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/S1600536808014487/sj2499sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014487/sj2499Isup2.hkl

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

C20H16N2O4·CH4O	Z = 4
Mr = 380.39	F000 = 800
Triclinic, P1	Dx = 1.383 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.3672 (2) Å	Cell parameters from 10651 reflections
b = 11.0813 (2) Å	θ = 1.0–30.0º
c = 20.3217 (3) Å	µ = 0.10 mm−1
α = 89.313 (1)º	T = 100.0 (1) K
β = 80.309 (1)º	Block, yellow
γ = 79.641 (1)º	0.50 × 0.34 × 0.17 mm
V = 1826.73 (6) Å3

Bruker SMART APEX2 CCD area-detector diffractometer	10651 independent reflections
Radiation source: fine-focus sealed tube	7203 reflections with I > 2σ(I)'
Monochromator: graphite	Rint = 0.034
Detector resolution: 8.33 pixels mm-1	θmax = 30.0º
T = 100.0(1) K	θmin = 1.0º
ω scans	h = −11→10
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −15→15
Tmin = 0.952, Tmax = 0.984	l = −28→28
42593 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056	H-atom parameters constrained
wR(F2) = 0.162	w = 1/[σ2(Fo2) + (0.0788P)2 + 0.3402P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
10651 reflections	Δρmax = 0.44 e Å−3
515 parameters	Δρmin = −0.34 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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

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.

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 > 2sigma(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
O1A	0.38240 (14)	1.21218 (9)	0.37963 (5)	0.0269 (3)
H1OA	0.3231	1.1862	0.4197	0.055 (6)*
O2A	0.70037 (13)	0.81358 (9)	0.39164 (5)	0.0243 (2)
O3A	0.83682 (14)	0.59449 (9)	0.48780 (5)	0.0268 (3)
H3OA	0.8948	0.5957	0.4431	0.054 (6)*
O4A	0.49475 (14)	0.34820 (10)	0.60844 (5)	0.0272 (3)
H4OA	0.4485	0.2903	0.6031	0.061 (7)*
N1A	0.94132 (15)	0.74067 (10)	0.29384 (6)	0.0193 (3)
H1NA	0.8739	0.7270	0.3329	0.042 (5)*
N2A	0.97260 (16)	0.52908 (11)	0.36228 (6)	0.0211 (3)
C1A	0.73415 (19)	1.05359 (13)	0.26751 (7)	0.0220 (3)
H1A	0.7991	1.0678	0.2273	0.026*
C2A	0.60758 (19)	1.14282 (13)	0.29478 (7)	0.0231 (3)
H2A	0.5870	1.2175	0.2736	0.028*
C3A	0.50713 (19)	1.12139 (12)	0.35571 (7)	0.0215 (3)
C4A	0.53930 (19)	1.01151 (12)	0.38853 (7)	0.0213 (3)
H4A	0.4740	0.9996	0.4290	0.026*
C5A	0.66928 (18)	0.91814 (12)	0.36127 (7)	0.0201 (3)
C6A	0.76932 (18)	0.93925 (12)	0.29904 (7)	0.0191 (3)
C7A	0.90059 (18)	0.84951 (12)	0.26841 (7)	0.0198 (3)
H7A	0.9618	0.8679	0.2282	0.024*
C8A	1.06914 (18)	0.64458 (12)	0.26672 (7)	0.0191 (3)
C9A	1.17540 (19)	0.65455 (13)	0.20737 (7)	0.0220 (3)
H9A	1.1653	0.7274	0.1840	0.026*
C10A	1.29635 (19)	0.55566 (14)	0.18314 (8)	0.0251 (3)
H10A	1.3668	0.5620	0.1432	0.030*
C11A	1.31301 (19)	0.44739 (14)	0.21809 (8)	0.0260 (3)
H11A	1.3952	0.3815	0.2017	0.031*
C12A	1.20798 (19)	0.43678 (13)	0.27732 (8)	0.0250 (3)
H12A	1.2205	0.3640	0.3007	0.030*
C13A	1.08334 (18)	0.53462 (13)	0.30223 (7)	0.0204 (3)
C14A	0.90878 (19)	0.43132 (13)	0.37372 (7)	0.0221 (3)
H14A	0.9346	0.3700	0.3408	0.026*
C15A	0.80086 (19)	0.41174 (12)	0.43391 (7)	0.0206 (3)
C16A	0.76986 (19)	0.49236 (12)	0.49003 (7)	0.0206 (3)
C17A	0.67009 (19)	0.46828 (13)	0.54807 (7)	0.0223 (3)
H17A	0.6535	0.5202	0.5851	0.027*
C18A	0.59436 (19)	0.36593 (13)	0.55096 (7)	0.0220 (3)
C19A	0.6219 (2)	0.28485 (13)	0.49599 (7)	0.0243 (3)
H19A	0.5723	0.2159	0.4983	0.029*
C20A	0.72290 (19)	0.30880 (13)	0.43892 (7)	0.0241 (3)
H20A	0.7405	0.2555	0.4024	0.029*
O1B	1.06277 (14)	0.29566 (9)	0.12539 (5)	0.0263 (2)
H1OB	1.1264	0.3111	0.0813	0.060 (7)*
O2B	0.78690 (13)	0.70842 (9)	0.11637 (5)	0.0246 (2)
O3B	0.65725 (14)	0.90440 (9)	0.01575 (5)	0.0263 (2)
H3OB	0.5866	0.9158	0.0575	0.050 (6)*
O4B	1.01686 (14)	1.13045 (10)	−0.11108 (5)	0.0269 (2)
H4OB	1.0777	1.1886	−0.1138	0.065 (7)*
N1B	0.53881 (15)	0.78591 (10)	0.21044 (6)	0.0188 (3)
H1NB	0.6050	0.7965	0.1739	0.043 (6)*
N2B	0.50773 (16)	0.98985 (11)	0.13603 (6)	0.0212 (3)
C1B	0.72248 (19)	0.46765 (13)	0.23763 (7)	0.0218 (3)
H1B	0.6540	0.4555	0.2773	0.026*
C2B	0.84138 (19)	0.37362 (13)	0.21012 (7)	0.0227 (3)
H2B	0.8535	0.2978	0.2306	0.027*
C3B	0.94691 (19)	0.39181 (12)	0.14999 (7)	0.0209 (3)
C4B	0.92878 (19)	0.50368 (13)	0.11862 (7)	0.0218 (3)
H4B	0.9983	0.5136	0.0789	0.026*
C5B	0.80678 (18)	0.60236 (12)	0.14599 (7)	0.0195 (3)
C6B	0.70035 (18)	0.58425 (12)	0.20722 (7)	0.0189 (3)
C7B	0.57163 (18)	0.67648 (12)	0.23642 (7)	0.0191 (3)
H7B	0.5062	0.6598	0.2760	0.023*
C8B	0.40985 (18)	0.88345 (12)	0.23481 (7)	0.0186 (3)
C9B	0.30337 (19)	0.87881 (13)	0.29475 (7)	0.0223 (3)
H9B	0.3152	0.8092	0.3208	0.027*
C10B	0.17954 (19)	0.97810 (14)	0.31555 (8)	0.0249 (3)
H10B	0.1086	0.9754	0.3558	0.030*
C11B	0.16100 (19)	1.08150 (14)	0.27664 (8)	0.0264 (3)
H11B	0.0766	1.1474	0.2906	0.032*
C12B	0.26700 (19)	1.08732 (13)	0.21731 (8)	0.0245 (3)
H12B	0.2533	1.1570	0.1914	0.029*
C13B	0.39474 (19)	0.98924 (13)	0.19586 (7)	0.0204 (3)
C14B	0.56811 (19)	1.08790 (13)	0.12067 (7)	0.0222 (3)
H14B	0.5372	1.1544	0.1504	0.027*
C15B	0.68020 (19)	1.09985 (12)	0.06030 (7)	0.0212 (3)
C16B	0.72244 (19)	1.00770 (12)	0.00920 (7)	0.0211 (3)
C17B	0.83261 (19)	1.02095 (13)	−0.04789 (7)	0.0225 (3)
H17B	0.8579	0.9607	−0.0814	0.027*
C18B	0.90569 (19)	1.12444 (13)	−0.05529 (7)	0.0222 (3)
C19B	0.8645 (2)	1.21803 (13)	−0.00595 (7)	0.0253 (3)
H19B	0.9114	1.2883	−0.0115	0.030*
C20B	0.7541 (2)	1.20413 (13)	0.05044 (7)	0.0255 (3)
H20B	0.7275	1.2658	0.0832	0.031*
O5A	0.78442 (15)	0.63854 (10)	−0.01097 (6)	0.0355 (3)
H5OA	0.7819	0.6756	0.0250	0.053*
C21A	0.6263 (3)	0.6108 (3)	−0.00516 (12)	0.0693 (8)
H21A	0.5458	0.6836	0.0074	0.104*
H21B	0.6128	0.5498	0.0283	0.104*
H21C	0.6116	0.5797	−0.0472	0.104*
O5B	0.77865 (16)	0.87056 (10)	0.50980 (6)	0.0370 (3)
H5OB	0.7381	0.8399	0.4761	0.055*
C21B	0.9533 (3)	0.84547 (17)	0.50003 (11)	0.0475 (5)
H21D	0.9915	0.7584	0.4966	0.071*
H21E	0.9903	0.8780	0.5372	0.071*
H21F	0.9964	0.8831	0.4597	0.071*

	U11	U22	U33	U12	U13	U23
O1A	0.0347 (7)	0.0192 (5)	0.0245 (6)	0.0013 (5)	−0.0056 (5)	0.0008 (4)
O2A	0.0273 (6)	0.0196 (5)	0.0238 (5)	−0.0020 (4)	−0.0007 (5)	0.0079 (4)
O3A	0.0374 (7)	0.0182 (5)	0.0266 (6)	−0.0113 (5)	−0.0032 (5)	−0.0006 (4)
O4A	0.0351 (7)	0.0275 (6)	0.0202 (5)	−0.0114 (5)	−0.0025 (5)	0.0051 (4)
N1A	0.0202 (7)	0.0189 (6)	0.0191 (6)	−0.0048 (5)	−0.0029 (5)	0.0028 (4)
N2A	0.0232 (7)	0.0197 (6)	0.0207 (6)	−0.0045 (5)	−0.0039 (5)	0.0032 (5)
C1A	0.0274 (8)	0.0213 (7)	0.0196 (7)	−0.0087 (6)	−0.0065 (6)	0.0048 (5)
C2A	0.0318 (9)	0.0162 (6)	0.0238 (7)	−0.0063 (6)	−0.0101 (7)	0.0057 (5)
C3A	0.0253 (8)	0.0174 (6)	0.0233 (7)	−0.0037 (6)	−0.0082 (6)	−0.0016 (5)
C4A	0.0250 (8)	0.0200 (7)	0.0193 (7)	−0.0052 (6)	−0.0033 (6)	0.0028 (5)
C5A	0.0227 (8)	0.0182 (6)	0.0214 (7)	−0.0067 (6)	−0.0063 (6)	0.0039 (5)
C6A	0.0202 (8)	0.0182 (6)	0.0209 (7)	−0.0061 (6)	−0.0067 (6)	0.0034 (5)
C7A	0.0225 (8)	0.0217 (7)	0.0177 (7)	−0.0086 (6)	−0.0054 (6)	0.0030 (5)
C8A	0.0173 (7)	0.0204 (6)	0.0204 (7)	−0.0048 (5)	−0.0042 (6)	−0.0001 (5)
C9A	0.0233 (8)	0.0238 (7)	0.0207 (7)	−0.0075 (6)	−0.0060 (6)	0.0028 (5)
C10A	0.0214 (8)	0.0304 (8)	0.0236 (7)	−0.0080 (6)	−0.0007 (6)	−0.0029 (6)
C11A	0.0201 (8)	0.0247 (7)	0.0321 (8)	−0.0020 (6)	−0.0029 (7)	−0.0064 (6)
C12A	0.0246 (8)	0.0210 (7)	0.0299 (8)	−0.0041 (6)	−0.0061 (7)	−0.0003 (6)
C13A	0.0227 (8)	0.0206 (7)	0.0194 (7)	−0.0061 (6)	−0.0054 (6)	0.0018 (5)
C14A	0.0253 (8)	0.0198 (6)	0.0222 (7)	−0.0046 (6)	−0.0065 (6)	0.0012 (5)
C15A	0.0244 (8)	0.0181 (6)	0.0200 (7)	−0.0053 (6)	−0.0043 (6)	0.0023 (5)
C16A	0.0239 (8)	0.0169 (6)	0.0228 (7)	−0.0051 (6)	−0.0076 (6)	0.0036 (5)
C17A	0.0284 (9)	0.0194 (6)	0.0202 (7)	−0.0041 (6)	−0.0069 (6)	0.0008 (5)
C18A	0.0244 (8)	0.0218 (7)	0.0198 (7)	−0.0037 (6)	−0.0049 (6)	0.0056 (5)
C19A	0.0290 (9)	0.0210 (7)	0.0246 (8)	−0.0096 (6)	−0.0042 (6)	0.0033 (6)
C20A	0.0292 (9)	0.0208 (7)	0.0235 (7)	−0.0077 (6)	−0.0038 (6)	−0.0017 (6)
O1B	0.0326 (7)	0.0182 (5)	0.0253 (6)	0.0023 (4)	−0.0047 (5)	0.0008 (4)
O2B	0.0270 (6)	0.0182 (5)	0.0257 (5)	−0.0024 (4)	0.0011 (5)	0.0069 (4)
O3B	0.0342 (7)	0.0198 (5)	0.0261 (6)	−0.0106 (5)	−0.0024 (5)	−0.0001 (4)
O4B	0.0331 (7)	0.0283 (6)	0.0203 (5)	−0.0107 (5)	−0.0024 (5)	0.0052 (4)
N1B	0.0196 (6)	0.0179 (5)	0.0188 (6)	−0.0040 (5)	−0.0019 (5)	0.0013 (4)
N2B	0.0234 (7)	0.0198 (6)	0.0206 (6)	−0.0041 (5)	−0.0040 (5)	0.0029 (5)
C1B	0.0254 (8)	0.0227 (7)	0.0191 (7)	−0.0080 (6)	−0.0049 (6)	0.0060 (5)
C2B	0.0290 (9)	0.0174 (6)	0.0234 (7)	−0.0065 (6)	−0.0072 (6)	0.0059 (5)
C3B	0.0241 (8)	0.0187 (6)	0.0209 (7)	−0.0030 (6)	−0.0077 (6)	0.0000 (5)
C4B	0.0235 (8)	0.0208 (7)	0.0203 (7)	−0.0038 (6)	−0.0018 (6)	0.0029 (5)
C5B	0.0209 (8)	0.0178 (6)	0.0210 (7)	−0.0061 (6)	−0.0042 (6)	0.0043 (5)
C6B	0.0196 (8)	0.0185 (6)	0.0201 (7)	−0.0051 (6)	−0.0059 (6)	0.0027 (5)
C7B	0.0208 (8)	0.0219 (7)	0.0163 (6)	−0.0076 (6)	−0.0040 (6)	0.0031 (5)
C8B	0.0170 (7)	0.0192 (6)	0.0207 (7)	−0.0042 (5)	−0.0048 (6)	−0.0014 (5)
C9B	0.0227 (8)	0.0240 (7)	0.0214 (7)	−0.0079 (6)	−0.0034 (6)	0.0012 (5)
C10B	0.0211 (8)	0.0316 (8)	0.0222 (7)	−0.0079 (6)	−0.0004 (6)	−0.0036 (6)
C11B	0.0196 (8)	0.0255 (7)	0.0335 (8)	−0.0029 (6)	−0.0036 (7)	−0.0063 (6)
C12B	0.0261 (8)	0.0194 (7)	0.0293 (8)	−0.0042 (6)	−0.0080 (7)	0.0013 (6)
C13B	0.0218 (8)	0.0202 (6)	0.0207 (7)	−0.0056 (6)	−0.0057 (6)	−0.0003 (5)
C14B	0.0262 (8)	0.0197 (7)	0.0213 (7)	−0.0041 (6)	−0.0063 (6)	0.0003 (5)
C15B	0.0255 (8)	0.0188 (6)	0.0206 (7)	−0.0048 (6)	−0.0074 (6)	0.0024 (5)
C16B	0.0252 (8)	0.0184 (6)	0.0222 (7)	−0.0060 (6)	−0.0091 (6)	0.0042 (5)
C17B	0.0280 (9)	0.0200 (7)	0.0202 (7)	−0.0042 (6)	−0.0063 (6)	0.0004 (5)
C18B	0.0246 (8)	0.0244 (7)	0.0187 (7)	−0.0059 (6)	−0.0062 (6)	0.0066 (5)
C19B	0.0315 (9)	0.0204 (7)	0.0262 (8)	−0.0095 (6)	−0.0061 (7)	0.0037 (6)
C20B	0.0323 (9)	0.0221 (7)	0.0234 (8)	−0.0085 (6)	−0.0045 (7)	0.0005 (6)
O5A	0.0446 (8)	0.0320 (6)	0.0259 (6)	−0.0036 (5)	0.0020 (5)	−0.0061 (5)
C21A	0.0710 (18)	0.0941 (19)	0.0535 (14)	−0.0471 (15)	−0.0052 (12)	−0.0218 (13)
O5B	0.0476 (8)	0.0312 (6)	0.0264 (6)	0.0059 (6)	−0.0035 (6)	−0.0034 (5)
C21B	0.0521 (14)	0.0349 (10)	0.0598 (13)	−0.0127 (9)	−0.0163 (11)	0.0007 (9)

O1A—C3A	1.3420 (17)	O4B—C18B	1.3493 (18)
O1A—H1OA	0.9500	O4B—H4OB	0.8863
O2A—C5A	1.3113 (16)	N1B—C7B	1.3183 (17)
O3A—C16A	1.3473 (16)	N1B—C8B	1.4112 (18)
O3A—H3OA	0.9560	N1B—H1NB	0.8691
O4A—C18A	1.3503 (18)	N2B—C14B	1.2921 (18)
O4A—H4OA	0.8240	N2B—C13B	1.4097 (19)
N1A—C7A	1.3169 (17)	C1B—C2B	1.357 (2)
N1A—C8A	1.4098 (18)	C1B—C6B	1.4209 (18)
N1A—H1NA	0.9215	C1B—H1B	0.9300
N2A—C14A	1.2934 (18)	C2B—C3B	1.417 (2)
N2A—C13A	1.4105 (19)	C2B—H2B	0.9300
C1A—C2A	1.358 (2)	C3B—C4B	1.3828 (19)
C1A—C6A	1.4186 (19)	C4B—C5B	1.403 (2)
C1A—H1A	0.9300	C4B—H4B	0.9300
C2A—C3A	1.418 (2)	C5B—C6B	1.438 (2)
C2A—H2A	0.9300	C6B—C7B	1.400 (2)
C3A—C4A	1.3868 (19)	C7B—H7B	0.9300
C4A—C5A	1.402 (2)	C8B—C9B	1.389 (2)
C4A—H4A	0.9300	C8B—C13B	1.4053 (19)
C5A—C6A	1.436 (2)	C9B—C10B	1.384 (2)
C6A—C7A	1.405 (2)	C9B—H9B	0.9300
C7A—H7A	0.9300	C10B—C11B	1.385 (2)
C8A—C9A	1.389 (2)	C10B—H10B	0.9300
C8A—C13A	1.4054 (19)	C11B—C12B	1.380 (2)
C9A—C10A	1.383 (2)	C11B—H11B	0.9300
C9A—H9A	0.9300	C12B—C13B	1.397 (2)
C10A—C11A	1.384 (2)	C12B—H12B	0.9300
C10A—H10A	0.9300	C14B—C15B	1.434 (2)
C11A—C12A	1.383 (2)	C14B—H14B	0.9300
C11A—H11A	0.9300	C15B—C20B	1.4028 (19)
C12A—C13A	1.396 (2)	C15B—C16B	1.4206 (19)
C12A—H12A	0.9300	C16B—C17B	1.379 (2)
C14A—C15A	1.432 (2)	C17B—C18B	1.389 (2)
C14A—H14A	0.9300	C17B—H17B	0.9300
C15A—C20A	1.4069 (19)	C18B—C19B	1.407 (2)
C15A—C16A	1.4169 (19)	C19B—C20B	1.371 (2)
C16A—C17A	1.378 (2)	C19B—H19B	0.9300
C17A—C18A	1.391 (2)	C20B—H20B	0.9300
C17A—H17A	0.9300	O5A—C21A	1.398 (2)
C18A—C19A	1.404 (2)	O5A—H5OA	0.8380
C19A—C20A	1.368 (2)	C21A—H21A	0.9600
C19A—H19A	0.9300	C21A—H21B	0.9600
C20A—H20A	0.9300	C21A—H21C	0.9600
O1B—C3B	1.3428 (17)	O5B—C21B	1.418 (2)
O1B—H1OB	0.9923	O5B—H5OB	0.9079
O2B—C5B	1.3106 (16)	C21B—H21D	0.9600
O3B—C16B	1.3498 (16)	C21B—H21E	0.9600
O3B—H3OB	0.9451	C21B—H21F	0.9600
C3A—O1A—H1OA	108.9	C2B—C1B—C6B	121.45 (14)
C16A—O3A—H3OA	104.7	C2B—C1B—H1B	119.3
C18A—O4A—H4OA	109.0	C6B—C1B—H1B	119.3
C7A—N1A—C8A	127.48 (13)	C1B—C2B—C3B	119.54 (13)
C7A—N1A—H1NA	114.2	C1B—C2B—H2B	120.2
C8A—N1A—H1NA	118.2	C3B—C2B—H2B	120.2
C14A—N2A—C13A	118.47 (12)	O1B—C3B—C4B	122.39 (14)
C2A—C1A—C6A	121.38 (14)	O1B—C3B—C2B	116.82 (12)
C2A—C1A—H1A	119.3	C4B—C3B—C2B	120.78 (13)
C6A—C1A—H1A	119.3	C3B—C4B—C5B	120.80 (14)
C1A—C2A—C3A	119.60 (13)	C3B—C4B—H4B	119.6
C1A—C2A—H2A	120.2	C5B—C4B—H4B	119.6
C3A—C2A—H2A	120.2	O2B—C5B—C4B	121.44 (13)
O1A—C3A—C4A	122.46 (14)	O2B—C5B—C6B	120.08 (13)
O1A—C3A—C2A	116.87 (12)	C4B—C5B—C6B	118.46 (12)
C4A—C3A—C2A	120.67 (13)	C7B—C6B—C1B	118.99 (13)
C3A—C4A—C5A	120.66 (14)	C7B—C6B—C5B	122.01 (12)
C3A—C4A—H4A	119.7	C1B—C6B—C5B	118.96 (13)
C5A—C4A—H4A	119.7	N1B—C7B—C6B	123.07 (13)
O2A—C5A—C4A	121.24 (13)	N1B—C7B—H7B	118.5
O2A—C5A—C6A	120.17 (13)	C6B—C7B—H7B	118.5
C4A—C5A—C6A	118.59 (12)	C9B—C8B—C13B	120.41 (13)
C7A—C6A—C1A	119.15 (13)	C9B—C8B—N1B	122.93 (12)
C7A—C6A—C5A	121.77 (12)	C13B—C8B—N1B	116.65 (13)
C1A—C6A—C5A	119.08 (13)	C10B—C9B—C8B	119.76 (14)
N1A—C7A—C6A	123.28 (13)	C10B—C9B—H9B	120.1
N1A—C7A—H7A	118.4	C8B—C9B—H9B	120.1
C6A—C7A—H7A	118.4	C9B—C10B—C11B	120.23 (15)
C9A—C8A—C13A	120.45 (13)	C9B—C10B—H10B	119.9
C9A—C8A—N1A	122.92 (12)	C11B—C10B—H10B	119.9
C13A—C8A—N1A	116.61 (13)	C12B—C11B—C10B	120.40 (14)
C10A—C9A—C8A	119.76 (13)	C12B—C11B—H11B	119.8
C10A—C9A—H9A	120.1	C10B—C11B—H11B	119.8
C8A—C9A—H9A	120.1	C11B—C12B—C13B	120.44 (14)
C9A—C10A—C11A	120.34 (15)	C11B—C12B—H12B	119.8
C9A—C10A—H10A	119.8	C13B—C12B—H12B	119.8
C11A—C10A—H10A	119.8	C12B—C13B—C8B	118.71 (14)
C12A—C11A—C10A	120.27 (14)	C12B—C13B—N2B	123.18 (13)
C12A—C11A—H11A	119.9	C8B—C13B—N2B	118.09 (13)
C10A—C11A—H11A	119.9	N2B—C14B—C15B	123.63 (13)
C11A—C12A—C13A	120.43 (14)	N2B—C14B—H14B	118.2
C11A—C12A—H12A	119.8	C15B—C14B—H14B	118.2
C13A—C12A—H12A	119.8	C20B—C15B—C16B	117.67 (14)
C12A—C13A—C8A	118.72 (14)	C20B—C15B—C14B	120.20 (13)
C12A—C13A—N2A	122.94 (13)	C16B—C15B—C14B	122.12 (13)
C8A—C13A—N2A	118.32 (13)	O3B—C16B—C17B	118.42 (12)
N2A—C14A—C15A	124.04 (13)	O3B—C16B—C15B	120.78 (13)
N2A—C14A—H14A	118.0	C17B—C16B—C15B	120.79 (13)
C15A—C14A—H14A	118.0	C16B—C17B—C18B	119.86 (13)
C20A—C15A—C16A	117.79 (13)	C16B—C17B—H17B	120.1
C20A—C15A—C14A	119.92 (13)	C18B—C17B—H17B	120.1
C16A—C15A—C14A	122.29 (13)	O4B—C18B—C17B	117.28 (13)
O3A—C16A—C17A	118.50 (12)	O4B—C18B—C19B	122.12 (13)
O3A—C16A—C15A	120.74 (13)	C17B—C18B—C19B	120.60 (14)
C17A—C16A—C15A	120.76 (13)	C20B—C19B—C18B	118.98 (13)
C16A—C17A—C18A	119.73 (13)	C20B—C19B—H19B	120.5
C16A—C17A—H17A	120.1	C18B—C19B—H19B	120.5
C18A—C17A—H17A	120.1	C19B—C20B—C15B	122.06 (13)
O4A—C18A—C17A	117.35 (13)	C19B—C20B—H20B	119.0
O4A—C18A—C19A	121.91 (13)	C15B—C20B—H20B	119.0
C17A—C18A—C19A	120.74 (14)	C21A—O5A—H5OA	103.6
C20A—C19A—C18A	119.01 (13)	O5A—C21A—H21A	109.5
C20A—C19A—H19A	120.5	O5A—C21A—H21B	109.5
C18A—C19A—H19A	120.5	H21A—C21A—H21B	109.5
C19A—C20A—C15A	121.93 (13)	O5A—C21A—H21C	109.5
C19A—C20A—H20A	119.0	H21A—C21A—H21C	109.5
C15A—C20A—H20A	119.0	H21B—C21A—H21C	109.5
C3B—O1B—H1OB	113.4	C21B—O5B—H5OB	112.5
C16B—O3B—H3OB	103.5	O5B—C21B—H21D	109.5
C18B—O4B—H4OB	118.9	O5B—C21B—H21E	109.5
C7B—N1B—C8B	127.42 (13)	H21D—C21B—H21E	109.5
C7B—N1B—H1NB	114.3	O5B—C21B—H21F	109.5
C8B—N1B—H1NB	118.3	H21D—C21B—H21F	109.5
C14B—N2B—C13B	118.92 (12)	H21E—C21B—H21F	109.5
C6A—C1A—C2A—C3A	−0.6 (2)	C6B—C1B—C2B—C3B	0.4 (2)
C1A—C2A—C3A—O1A	−178.94 (13)	C1B—C2B—C3B—O1B	179.61 (13)
C1A—C2A—C3A—C4A	1.6 (2)	C1B—C2B—C3B—C4B	−0.8 (2)
O1A—C3A—C4A—C5A	178.95 (12)	O1B—C3B—C4B—C5B	−179.67 (12)
C2A—C3A—C4A—C5A	−1.6 (2)	C2B—C3B—C4B—C5B	0.8 (2)
C3A—C4A—C5A—O2A	−179.61 (13)	C3B—C4B—C5B—O2B	−179.15 (13)
C3A—C4A—C5A—C6A	0.6 (2)	C3B—C4B—C5B—C6B	−0.4 (2)
C2A—C1A—C6A—C7A	179.34 (13)	C2B—C1B—C6B—C7B	177.55 (13)
C2A—C1A—C6A—C5A	−0.4 (2)	C2B—C1B—C6B—C5B	0.0 (2)
O2A—C5A—C6A—C7A	0.9 (2)	O2B—C5B—C6B—C7B	1.3 (2)
C4A—C5A—C6A—C7A	−179.35 (13)	C4B—C5B—C6B—C7B	−177.51 (13)
O2A—C5A—C6A—C1A	−179.39 (12)	O2B—C5B—C6B—C1B	178.79 (12)
C4A—C5A—C6A—C1A	0.36 (19)	C4B—C5B—C6B—C1B	0.00 (19)
C8A—N1A—C7A—C6A	179.33 (12)	C8B—N1B—C7B—C6B	178.07 (12)
C1A—C6A—C7A—N1A	−179.54 (13)	C1B—C6B—C7B—N1B	−177.73 (13)
C5A—C6A—C7A—N1A	0.2 (2)	C5B—C6B—C7B—N1B	−0.2 (2)
C7A—N1A—C8A—C9A	1.4 (2)	C7B—N1B—C8B—C9B	4.9 (2)
C7A—N1A—C8A—C13A	−177.32 (13)	C7B—N1B—C8B—C13B	−176.36 (13)
C13A—C8A—C9A—C10A	−0.2 (2)	C13B—C8B—C9B—C10B	1.3 (2)
N1A—C8A—C9A—C10A	−178.88 (12)	N1B—C8B—C9B—C10B	179.98 (13)
C8A—C9A—C10A—C11A	−0.7 (2)	C8B—C9B—C10B—C11B	0.4 (2)
C9A—C10A—C11A—C12A	0.5 (2)	C9B—C10B—C11B—C12B	−0.9 (2)
C10A—C11A—C12A—C13A	0.5 (2)	C10B—C11B—C12B—C13B	−0.2 (2)
C11A—C12A—C13A—C8A	−1.3 (2)	C11B—C12B—C13B—C8B	1.9 (2)
C11A—C12A—C13A—N2A	179.96 (13)	C11B—C12B—C13B—N2B	−179.56 (13)
C9A—C8A—C13A—C12A	1.2 (2)	C9B—C8B—C13B—C12B	−2.4 (2)
N1A—C8A—C13A—C12A	179.95 (12)	N1B—C8B—C13B—C12B	178.80 (12)
C9A—C8A—C13A—N2A	179.95 (12)	C9B—C8B—C13B—N2B	178.95 (12)
N1A—C8A—C13A—N2A	−1.28 (18)	N1B—C8B—C13B—N2B	0.20 (18)
C14A—N2A—C13A—C12A	−43.96 (19)	C14B—N2B—C13B—C12B	43.0 (2)
C14A—N2A—C13A—C8A	137.33 (14)	C14B—N2B—C13B—C8B	−138.49 (14)
C13A—N2A—C14A—C15A	177.04 (13)	C13B—N2B—C14B—C15B	−178.21 (13)
N2A—C14A—C15A—C20A	172.92 (14)	N2B—C14B—C15B—C20B	−173.14 (14)
N2A—C14A—C15A—C16A	−7.8 (2)	N2B—C14B—C15B—C16B	5.9 (2)
C20A—C15A—C16A—O3A	−178.04 (13)	C20B—C15B—C16B—O3B	179.28 (13)
C14A—C15A—C16A—O3A	2.7 (2)	C14B—C15B—C16B—O3B	0.2 (2)
C20A—C15A—C16A—C17A	1.7 (2)	C20B—C15B—C16B—C17B	0.1 (2)
C14A—C15A—C16A—C17A	−177.56 (13)	C14B—C15B—C16B—C17B	−178.99 (13)
O3A—C16A—C17A—C18A	177.61 (13)	O3B—C16B—C17B—C18B	−178.07 (13)
C15A—C16A—C17A—C18A	−2.2 (2)	C15B—C16B—C17B—C18B	1.1 (2)
C16A—C17A—C18A—O4A	−178.44 (13)	C16B—C17B—C18B—O4B	177.70 (12)
C16A—C17A—C18A—C19A	1.8 (2)	C16B—C17B—C18B—C19B	−2.0 (2)
O4A—C18A—C19A—C20A	179.29 (13)	O4B—C18B—C19B—C20B	−178.04 (13)
C17A—C18A—C19A—C20A	−0.9 (2)	C17B—C18B—C19B—C20B	1.7 (2)
C18A—C19A—C20A—C15A	0.5 (2)	C18B—C19B—C20B—C15B	−0.4 (2)
C16A—C15A—C20A—C19A	−0.9 (2)	C16B—C15B—C20B—C19B	−0.5 (2)
C14A—C15A—C20A—C19A	178.42 (14)	C14B—C15B—C20B—C19B	178.67 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1OA···O5Bi	0.95	1.71	2.6610 (16)	176
O3A—H3OA···N2A	0.96	1.78	2.6637 (16)	153
O4A—H4OA···O2Aii	0.82	1.83	2.6330 (16)	164
N1A—H1NA···O2A	0.92	1.84	2.6021 (16)	138
N1A—H1NA···N2A	0.92	2.31	2.7063 (16)	106
O1B—H1OB···O5Aiii	0.99	1.64	2.6205 (16)	170
O3B—H3OB···N2B	0.94	1.77	2.6526 (16)	154
O4B—H4OB···O2Biv	0.89	1.74	2.6241 (16)	174
N1B—H1NB···O2B	0.87	1.88	2.6006 (16)	139
N1B—H1NB···N2B	0.87	2.32	2.7020 (16)	107
O5A—H5OA···O2B	0.84	1.91	2.7145 (16)	162
O5A—H5OA···O3B	0.84	2.58	2.9703 (15)	110
O5B—H5OB···O2A	0.91	1.83	2.7034 (16)	160
C4A—H4A···O5Bi	0.93	2.48	3.165 (2)	131
C4B—H4B···O5Aiii	0.93	2.48	3.1596 (19)	130
C7A—H7A···O4Biv	0.93	2.36	3.1691 (17)	146
C7B—H7B···O4Aii	0.93	2.35	3.1253 (17)	141
C12B—H12B···O1Bv	0.93	2.55	3.3603 (18)	146
C21B—H21D···O3A	0.96	2.44	3.134 (2)	129
C21B—H21D···Cg3vi	0.96	2.86	3.568 (2)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1OA⋯O5Bi	0.95	1.71	2.6610 (16)	176
O3A—H3OA⋯N2A	0.96	1.78	2.6637 (16)	153
O4A—H4OA⋯O2Aii	0.82	1.83	2.6330 (16)	164
N1A—H1NA⋯O2A	0.92	1.84	2.6021 (16)	138
N1A—H1NA⋯N2A	0.92	2.31	2.7063 (16)	106
O1B—H1OB⋯O5Aiii	0.99	1.64	2.6205 (16)	170
O3B—H3OB⋯N2B	0.94	1.77	2.6526 (16)	154
O4B—H4OB⋯O2Biv	0.89	1.74	2.6241 (16)	174
N1B—H1NB⋯O2B	0.87	1.88	2.6006 (16)	139
N1B—H1NB⋯N2B	0.87	2.32	2.7020 (16)	107
O5A—H5OA⋯O2B	0.84	1.91	2.7145 (16)	162
O5A—H5OA⋯O3B	0.84	2.58	2.9703 (15)	110
O5B—H5OB⋯O2A	0.91	1.83	2.7034 (16)	160
C4A—H4A⋯O5Bi	0.93	2.48	3.165 (2)	131
C4B—H4B⋯O5Aiii	0.93	2.48	3.1596 (19)	130
C7A—H7A⋯O4Biv	0.93	2.36	3.1691 (17)	146
C7B—H7B⋯O4Aii	0.93	2.35	3.1253 (17)	141
C12B—H12B⋯O1Bv	0.93	2.55	3.3603 (18)	146
C21B—H21D⋯O3A	0.96	2.44	3.134 (2)	129
C21B—H21D⋯Cg3vi	0.96	2.86	3.568 (2)	132

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) . Cg3 is the centroid of the C15A–C20A ring.