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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): o1290–o1291.
Published online 2008 June 19. doi:  10.1107/S1600536808017844
PMCID: PMC2961660

2-Amino-N-(2-benz­yloxy-3-methoxy­benzyl­idene)aniline

Abstract

The title compound, C21H20N2O2, a Schiff base ligand, contains two independent mol­ecules (A and B) in the asymmetric unit, with similar conformations. In mol­ecule A, the central benzene ring forms dihedral angles of 30.79 (13) and 23.56 (13)°, respectively, with the amino and benzyl benzene rings, while in mol­ecule B these angles are 32.30 (13) and 13.13 (12)°. The mol­ecular structure is stabilized by intra­molecular N—H(...)N and C—H(...)O hydrogen bonds. The crystal structure is stabilized by N—H(...)N hydrogen bonds and N—H(...)π and C—H(...)π inter­actions.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For related structures, see: Al-Douh et al. (2006a [triangle],b [triangle], 2007 [triangle], 2008 [triangle]); Corden et al. (1996 [triangle]); Govindasamy et al. (1999 [triangle]); Pozharskii et al. (1966 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1290-scheme1.jpg

Experimental

Crystal data

  • C21H20N2O2
  • M r = 332.39
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1290-efi1.jpg
  • a = 12.0932 (2) Å
  • b = 13.7680 (3) Å
  • c = 20.5249 (4) Å
  • β = 99.149 (1)°
  • V = 3373.90 (11) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100.0 (1) K
  • 0.36 × 0.18 × 0.07 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker 2005 [triangle]) T min = 0.970, T max = 0.994
  • 37354 measured reflections
  • 7737 independent reflections
  • 4167 reflections with I > 2σ(I)
  • R int = 0.082

Refinement

  • R[F 2 > 2σ(F 2)] = 0.070
  • wR(F 2) = 0.192
  • S = 1.03
  • 7737 reflections
  • 465 parameters
  • 4 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.87 e Å−3
  • Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 [triangle]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017844/ci2609sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017844/ci2609Isup2.hkl

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

Acknowledgments

We thank the Malaysian Government and Universiti Sains Malaysia (USM) for an IRPA short-term grant (304/PKIMIA/638007) to conduct this work. MHA thanks the Yemen Government and Hadhramout University of Science and Technology (HUST) for financial scholarship support. HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

supplementary crystallographic information

Comment

Mono-anil, is a Schiff base compound prepared from an equimolar amount of o-phenylenediamine and an aromatic or heterocyclic aldehyde as the first stage to produce 2-substituted benzimidazole derivatives following spontaneous oxidation by atmospheric oxygen (Pozharskii et al., 1966). In our previous reports (Al-Douh et al., 2007,2006a,b; Al-Douh et al., 2008), we have reported crystal structures of 2-(2-benzyloxy -3-methoxyphenyl)-1-H-benzimidazole, benzyl o-vanillin and a derivative of the title compound, 2-amino-N-(2-hydroxy-3-methoxybenzylidene) benzeneamine. Continuing our investigation on the reaction mechanism of benzyl o-vanillin with o-phenylenediamine, we successfully synthesized the title compound, as a new amino benzeneamine derivative. We present here its crystal structure.

The bond lengths and angles in the title compound have normal values (Allen et al., 1987) and are comparable with those a realated structure (Al-Douh et al., 2008). The asymmetric unit contains two independent molecules [A and B] with almost similar conformations (Fig.1). In both A and B, the methoxy group is almost coplanar with the attached benzene ring [C21–O2–C12–C11 = -3.6 (4)° for A and -2.5 (4)° for B]. In molecule A, the C1-C6 and C15-C20 rings form dihedral angles of 30.79 (13)° and 23.56 (13)°, respectively, with the C8-C13 ring, while in B these angles are 32.30 (13)° and 13.13 (12)°. Intramolecular C—H···O and N—H···N hydrogen bonds involving O1, O2 and N1 atoms generate S(5) or S(6) ring motifs.

The crystal packing of the title compound is controlled by N—H···N hydrogen bonds, and N—H···π and C—H···π interactions (Table 1).

Experimental

The title compound was synthesized following procedures reported earlier (Al-Douh et al., 2006a,b; Al-Douh et al., 2007). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a hexane solution at room temperature.

Refinement

Amino H atoms were located in a difference map and their positional parameters were refined with N-H distances restrained to 0.90 (1)Å. C-bound H atoms were positioned geometrically and refined using a riding model with C-H = 0.95 Å for aromatic and methyine H, 0.99 Å for methylene H, and 0.98 Å for methyl H atoms. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups. The highest peak is located at 0.60 Å from H7A and the deepest hole is located at 0.71 Å from N2A.

Figures

Fig. 1.
The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level. Intramolecular interactions are shown as dashed lines.

Crystal data

C21H20N2O2F000 = 1408
Mr = 332.39Dx = 1.309 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3259 reflections
a = 12.0932 (2) Åθ = 2.4–22.7º
b = 13.7680 (3) ŵ = 0.09 mm1
c = 20.5249 (4) ÅT = 100.0 (1) K
β = 99.149 (1)ºPlate, yellow
V = 3373.90 (11) Å30.36 × 0.18 × 0.07 mm
Z = 8

Data collection

Bruker SMART APEXII CCD area-detector diffractometer7737 independent reflections
Radiation source: fine-focus sealed tube4167 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.082
T = 100.0(1) Kθmax = 27.5º
[var phi] and ω scansθmin = 1.7º
Absorption correction: multi-scan(SADABS; Bruker 2005)h = −15→15
Tmin = 0.970, Tmax = 0.994k = −17→17
37354 measured reflectionsl = −26→26

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.070H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.192  w = 1/[σ2(Fo2) + (0.0781P)2 + 1.4666P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
7737 reflectionsΔρmax = 0.87 e Å3
465 parametersΔρmin = −0.38 e Å3
4 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O1A0.99391 (15)0.97464 (12)0.31812 (8)0.0232 (4)
O2A1.17303 (15)0.85898 (13)0.35794 (9)0.0257 (5)
N1A0.7858 (2)0.94192 (17)0.14556 (13)0.0358 (6)
N2A0.7063 (3)0.9977 (2)0.01884 (15)0.0516 (8)
H2AB0.657 (2)1.000 (3)−0.0199 (10)0.062*
H2AC0.748 (3)0.9432 (16)0.0317 (17)0.062*
C1A0.6378 (3)1.0482 (2)0.18465 (15)0.0353 (8)
H1A0.66361.03290.22960.042*
C2A0.5474 (3)1.1075 (2)0.16928 (18)0.0401 (8)
H2A0.51001.13200.20320.048*
C3A0.5108 (3)1.1317 (2)0.10576 (17)0.0395 (8)
H3A0.45001.17570.09540.047*
C4A0.5609 (3)1.0930 (2)0.05582 (15)0.0331 (7)
H4A0.53191.10970.01150.040*
C5A0.6517 (2)1.0309 (2)0.06765 (14)0.0283 (7)
C6A0.6950 (2)1.0082 (2)0.13495 (17)0.0344 (8)
C7A0.8502 (2)0.9488 (2)0.20040 (15)0.0311 (7)
H7A0.83540.99730.23080.037*
C8A0.9480 (2)0.88351 (19)0.21891 (13)0.0227 (6)
C9A0.9735 (2)0.8086 (2)0.17760 (13)0.0266 (7)
H9A0.92790.79870.13600.032*
C10A1.0642 (3)0.7494 (2)0.19684 (14)0.0283 (7)
H10A1.07970.69800.16880.034*
C11A1.1335 (2)0.76356 (19)0.25672 (14)0.0258 (7)
H11A1.19670.72270.26910.031*
C12A1.1104 (2)0.83792 (19)0.29868 (13)0.0224 (6)
C13A1.0167 (2)0.89782 (18)0.27938 (13)0.0192 (6)
C14A0.9679 (2)0.94967 (19)0.38311 (13)0.0246 (6)
H14A1.03790.94110.41490.030*
H14B0.92490.88820.38080.030*
C15A0.9004 (2)1.03068 (18)0.40466 (12)0.0201 (6)
C16A0.9483 (2)1.09881 (19)0.45039 (13)0.0217 (6)
H16A1.02511.09340.46910.026*
C17A0.8843 (2)1.17526 (19)0.46915 (13)0.0253 (7)
H17A0.91711.22080.50130.030*
C18A0.7739 (2)1.1844 (2)0.44110 (14)0.0268 (7)
H18A0.73091.23730.45320.032*
C19A0.7249 (2)1.1172 (2)0.39544 (14)0.0302 (7)
H19A0.64861.12380.37600.036*
C20A0.7880 (2)1.0401 (2)0.37814 (13)0.0250 (6)
H20A0.75380.99290.34760.030*
C21A1.2661 (2)0.7965 (2)0.38025 (15)0.0322 (7)
H21A1.30630.82060.42240.048*
H21B1.31670.79560.34740.048*
H21C1.23880.73060.38620.048*
O1B0.50904 (15)0.75379 (12)0.18231 (9)0.0226 (4)
O2B0.33148 (15)0.87429 (13)0.14797 (9)0.0282 (5)
N1B0.71887 (19)0.77598 (16)0.35724 (11)0.0243 (5)
N2B0.7842 (2)0.7181 (2)0.48460 (13)0.0408 (7)
H2BB0.830 (2)0.720 (2)0.5241 (9)0.049*
H2BC0.738 (2)0.7680 (17)0.4697 (15)0.049*
C1B0.8724 (2)0.6776 (2)0.32288 (15)0.0288 (7)
H1B0.85070.69570.27800.035*
C2B0.9638 (3)0.6175 (2)0.34035 (16)0.0328 (7)
H2B1.00440.59430.30750.039*
C3B0.9958 (3)0.5914 (2)0.40519 (16)0.0324 (7)
H3B1.05820.54940.41690.039*
C4B0.9382 (2)0.6254 (2)0.45366 (16)0.0313 (7)
H4B0.96170.60710.49830.038*
C5B0.8457 (2)0.68672 (19)0.43727 (14)0.0257 (7)
C6B0.8112 (2)0.71220 (18)0.37070 (14)0.0249 (7)
C7B0.6539 (2)0.77124 (19)0.30195 (14)0.0234 (6)
H7B0.66800.72350.27090.028*
C8B0.5580 (2)0.83669 (19)0.28451 (13)0.0218 (6)
C9B0.5342 (2)0.9077 (2)0.32963 (14)0.0264 (7)
H9B0.58070.91390.37130.032*
C10B0.4435 (2)0.9681 (2)0.31328 (14)0.0289 (7)
H10B0.42841.01640.34370.035*
C11B0.3737 (2)0.95954 (19)0.25302 (14)0.0256 (6)
H11B0.31111.00160.24260.031*
C12B0.3950 (2)0.88960 (19)0.20775 (14)0.0227 (6)
C13B0.4884 (2)0.82822 (18)0.22413 (13)0.0213 (6)
C14B0.5337 (2)0.78276 (19)0.11804 (13)0.0250 (7)
H14C0.57670.84430.12170.030*
H14D0.46340.79270.08680.030*
C15B0.6015 (2)0.70273 (18)0.09400 (13)0.0194 (6)
C16B0.5587 (2)0.64734 (18)0.03910 (13)0.0216 (6)
H16B0.48610.66070.01570.026*
C17B0.6221 (2)0.57224 (19)0.01840 (13)0.0242 (6)
H17B0.59350.5355−0.01970.029*
C18B0.7262 (2)0.55126 (19)0.05313 (14)0.0251 (6)
H18B0.76840.49890.03960.030*
C19B0.7695 (2)0.6061 (2)0.10765 (14)0.0254 (6)
H19B0.84170.59190.13150.030*
C20B0.7074 (2)0.68178 (19)0.12734 (13)0.0227 (6)
H20B0.73800.72000.16440.027*
C21B0.2325 (2)0.9329 (2)0.13189 (15)0.0323 (7)
H21D0.19310.91460.08810.048*
H21E0.25371.00150.13170.048*
H21F0.18330.92230.16480.048*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1A0.0304 (11)0.0202 (9)0.0203 (10)0.0033 (8)0.0083 (9)0.0007 (8)
O2A0.0230 (11)0.0288 (10)0.0235 (11)0.0054 (8)−0.0019 (9)−0.0040 (8)
N1A0.0313 (15)0.0302 (14)0.0435 (17)−0.0047 (12)−0.0018 (13)0.0055 (12)
N2A0.045 (2)0.071 (2)0.0371 (18)0.0098 (16)0.0005 (15)−0.0018 (17)
C1A0.0352 (19)0.049 (2)0.0198 (16)−0.0130 (16)−0.0011 (14)0.0015 (14)
C2A0.041 (2)0.0316 (17)0.050 (2)0.0033 (15)0.0119 (17)−0.0015 (16)
C3A0.044 (2)0.0312 (17)0.045 (2)−0.0025 (15)0.0121 (17)−0.0029 (16)
C4A0.0277 (18)0.0409 (18)0.0292 (17)−0.0002 (14)0.0004 (14)−0.0017 (14)
C5A0.0225 (16)0.0376 (17)0.0249 (16)−0.0042 (13)0.0044 (13)0.0023 (13)
C6A0.0217 (17)0.0251 (15)0.055 (2)−0.0074 (13)0.0005 (15)0.0126 (15)
C7A0.0273 (17)0.0327 (16)0.0312 (17)−0.0103 (13)−0.0021 (14)0.0136 (14)
C8A0.0199 (15)0.0256 (14)0.0234 (15)−0.0034 (12)0.0056 (12)0.0027 (12)
C9A0.0276 (17)0.0319 (16)0.0197 (15)−0.0084 (13)0.0018 (13)−0.0022 (13)
C10A0.0361 (18)0.0251 (15)0.0253 (16)−0.0009 (13)0.0093 (14)−0.0064 (13)
C11A0.0270 (17)0.0244 (14)0.0267 (16)0.0039 (12)0.0061 (13)0.0001 (12)
C12A0.0235 (16)0.0238 (14)0.0197 (14)−0.0034 (12)0.0029 (12)−0.0002 (12)
C13A0.0216 (15)0.0181 (13)0.0188 (14)−0.0012 (11)0.0058 (12)0.0011 (11)
C14A0.0303 (17)0.0243 (14)0.0202 (15)0.0018 (12)0.0069 (12)0.0025 (12)
C15A0.0224 (16)0.0228 (13)0.0168 (14)0.0004 (11)0.0080 (12)0.0044 (11)
C16A0.0199 (15)0.0252 (14)0.0204 (15)−0.0014 (12)0.0041 (12)0.0064 (12)
C17A0.0361 (18)0.0204 (14)0.0198 (15)−0.0012 (13)0.0057 (13)−0.0003 (12)
C18A0.0299 (18)0.0248 (15)0.0284 (16)0.0083 (13)0.0127 (14)0.0050 (13)
C19A0.0198 (16)0.0418 (17)0.0297 (17)0.0042 (13)0.0061 (13)0.0057 (14)
C20A0.0218 (16)0.0308 (15)0.0224 (15)−0.0021 (12)0.0031 (12)−0.0040 (12)
C21A0.0276 (17)0.0351 (16)0.0301 (17)0.0101 (13)−0.0070 (14)−0.0010 (14)
O1B0.0265 (11)0.0201 (9)0.0221 (10)0.0013 (8)0.0070 (9)−0.0013 (8)
O2B0.0255 (11)0.0281 (10)0.0292 (11)0.0050 (9)−0.0010 (9)−0.0041 (9)
N1B0.0229 (13)0.0244 (12)0.0266 (14)−0.0005 (10)0.0068 (11)0.0008 (10)
N2B0.0474 (19)0.0516 (18)0.0213 (14)0.0191 (14)−0.0011 (13)−0.0062 (13)
C1B0.0287 (17)0.0257 (15)0.0348 (17)−0.0035 (13)0.0136 (14)0.0047 (13)
C2B0.0287 (18)0.0246 (15)0.049 (2)0.0013 (13)0.0168 (15)0.0047 (14)
C3B0.0254 (17)0.0226 (15)0.049 (2)0.0021 (13)0.0063 (15)0.0020 (14)
C4B0.0290 (17)0.0251 (15)0.0366 (18)0.0001 (13)−0.0045 (14)−0.0028 (14)
C5B0.0254 (17)0.0235 (14)0.0278 (16)−0.0014 (12)0.0030 (13)−0.0046 (12)
C6B0.0242 (16)0.0185 (13)0.0309 (17)−0.0037 (12)0.0013 (13)−0.0016 (12)
C7B0.0272 (16)0.0232 (14)0.0216 (15)−0.0023 (12)0.0093 (13)−0.0011 (12)
C8B0.0211 (15)0.0233 (14)0.0230 (15)−0.0019 (12)0.0092 (12)0.0012 (12)
C9B0.0280 (17)0.0293 (15)0.0223 (15)0.0006 (13)0.0055 (13)−0.0036 (12)
C10B0.0327 (18)0.0238 (14)0.0321 (17)−0.0001 (13)0.0114 (14)−0.0079 (13)
C11B0.0226 (16)0.0236 (14)0.0320 (17)0.0036 (12)0.0088 (13)−0.0031 (13)
C12B0.0221 (16)0.0216 (14)0.0249 (15)−0.0008 (12)0.0056 (12)−0.0011 (12)
C13B0.0232 (16)0.0164 (13)0.0256 (15)−0.0015 (11)0.0076 (12)−0.0026 (11)
C14B0.0290 (17)0.0240 (14)0.0232 (15)0.0012 (12)0.0074 (13)0.0015 (12)
C15B0.0194 (15)0.0197 (13)0.0196 (14)−0.0018 (11)0.0050 (12)0.0032 (11)
C16B0.0195 (15)0.0255 (14)0.0198 (14)−0.0025 (12)0.0033 (12)0.0052 (12)
C17B0.0292 (17)0.0229 (14)0.0216 (15)−0.0069 (12)0.0071 (13)−0.0035 (12)
C18B0.0268 (17)0.0223 (14)0.0289 (16)0.0013 (12)0.0131 (13)0.0039 (12)
C19B0.0211 (16)0.0320 (15)0.0239 (16)−0.0003 (12)0.0060 (12)0.0049 (13)
C20B0.0240 (16)0.0271 (15)0.0173 (14)−0.0034 (12)0.0042 (12)−0.0024 (12)
C21B0.0266 (17)0.0299 (15)0.0381 (18)0.0077 (13)−0.0018 (14)0.0012 (14)

Geometric parameters (Å, °)

O1A—C13A1.377 (3)O1B—C13B1.385 (3)
O1A—C14A1.459 (3)O1B—C14B1.454 (3)
O2A—C12A1.358 (3)O2B—C12B1.357 (3)
O2A—C21A1.432 (3)O2B—C21B1.437 (3)
N1A—C7A1.266 (4)N1B—C7B1.275 (3)
N1A—C6A1.417 (4)N1B—C6B1.413 (3)
N2A—C5A1.363 (4)N2B—C5B1.383 (4)
N2A—H2AB0.917 (10)N2B—H2BB0.905 (10)
N2A—H2AC0.921 (10)N2B—H2BC0.905 (10)
C1A—C2A1.361 (4)C1B—C2B1.381 (4)
C1A—C6A1.431 (4)C1B—C6B1.403 (4)
C1A—H1A0.95C1B—H1B0.95
C2A—C3A1.350 (4)C2B—C3B1.374 (4)
C2A—H2A0.95C2B—H2B0.95
C3A—C4A1.378 (4)C3B—C4B1.384 (4)
C3A—H3A0.95C3B—H3B0.95
C4A—C5A1.383 (4)C4B—C5B1.399 (4)
C4A—H4A0.95C4B—H4B0.95
C5A—C6A1.432 (4)C5B—C6B1.408 (4)
C7A—C8A1.486 (4)C7B—C8B1.467 (4)
C7A—H7A0.95C7B—H7B0.95
C8A—C13A1.393 (4)C8B—C13B1.388 (4)
C8A—C9A1.401 (4)C8B—C9B1.408 (4)
C9A—C10A1.373 (4)C9B—C10B1.374 (4)
C9A—H9A0.95C9B—H9B0.95
C10A—C11A1.387 (4)C10B—C11B1.387 (4)
C10A—H10A0.95C10B—H10B0.95
C11A—C12A1.394 (4)C11B—C12B1.391 (4)
C11A—H11A0.95C11B—H11B0.95
C12A—C13A1.407 (4)C12B—C13B1.407 (4)
C14A—C15A1.491 (4)C14B—C15B1.503 (4)
C14A—H14A0.99C14B—H14C0.99
C14A—H14B0.99C14B—H14D0.99
C15A—C16A1.387 (4)C15B—C20B1.383 (4)
C15A—C20A1.387 (4)C15B—C16B1.391 (4)
C16A—C17A1.396 (4)C16B—C17B1.393 (4)
C16A—H16A0.95C16B—H16B0.95
C17A—C18A1.373 (4)C17B—C18B1.374 (4)
C17A—H17A0.95C17B—H17B0.95
C18A—C19A1.382 (4)C18B—C19B1.383 (4)
C18A—H18A0.95C18B—H18B0.95
C19A—C20A1.387 (4)C19B—C20B1.381 (4)
C19A—H19A0.95C19B—H19B0.95
C20A—H20A0.95C20B—H20B0.95
C21A—H21A0.98C21B—H21D0.98
C21A—H21B0.98C21B—H21E0.98
C21A—H21C0.98C21B—H21F0.98
C13A—O1A—C14A116.02 (19)C13B—O1B—C14B116.28 (19)
C12A—O2A—C21A117.1 (2)C12B—O2B—C21B116.9 (2)
C7A—N1A—C6A116.1 (3)C7B—N1B—C6B119.9 (2)
C5A—N2A—H2AB107 (2)C5B—N2B—H2BB109 (2)
C5A—N2A—H2AC112 (2)C5B—N2B—H2BC112 (2)
H2AB—N2A—H2AC122 (3)H2BB—N2B—H2BC122 (3)
C2A—C1A—C6A121.8 (3)C2B—C1B—C6B120.7 (3)
C2A—C1A—H1A119.1C2B—C1B—H1B119.6
C6A—C1A—H1A119.1C6B—C1B—H1B119.6
C3A—C2A—C1A120.0 (3)C3B—C2B—C1B120.0 (3)
C3A—C2A—H2A120.0C3B—C2B—H2B120.0
C1A—C2A—H2A120.0C1B—C2B—H2B120.0
C2A—C3A—C4A120.5 (3)C2B—C3B—C4B120.7 (3)
C2A—C3A—H3A119.7C2B—C3B—H3B119.6
C4A—C3A—H3A119.7C4B—C3B—H3B119.6
C3A—C4A—C5A122.6 (3)C3B—C4B—C5B120.4 (3)
C3A—C4A—H4A118.7C3B—C4B—H4B119.8
C5A—C4A—H4A118.7C5B—C4B—H4B119.8
N2A—C5A—C4A122.8 (3)N2B—C5B—C4B121.2 (3)
N2A—C5A—C6A119.4 (3)N2B—C5B—C6B119.6 (3)
C4A—C5A—C6A117.6 (3)C4B—C5B—C6B119.1 (3)
N1A—C6A—C1A126.1 (3)C1B—C6B—C5B119.1 (3)
N1A—C6A—C5A116.4 (3)C1B—C6B—N1B124.2 (3)
C1A—C6A—C5A117.4 (3)C5B—C6B—N1B116.6 (2)
N1A—C7A—C8A122.3 (3)N1B—C7B—C8B122.5 (2)
N1A—C7A—H7A118.9N1B—C7B—H7B118.8
C8A—C7A—H7A118.9C8B—C7B—H7B118.8
C13A—C8A—C9A119.1 (3)C13B—C8B—C9B119.1 (3)
C13A—C8A—C7A118.7 (2)C13B—C8B—C7B120.7 (2)
C9A—C8A—C7A122.3 (3)C9B—C8B—C7B120.2 (2)
C10A—C9A—C8A120.4 (3)C10B—C9B—C8B119.9 (3)
C10A—C9A—H9A119.8C10B—C9B—H9B120.1
C8A—C9A—H9A119.8C8B—C9B—H9B120.1
C9A—C10A—C11A120.9 (3)C9B—C10B—C11B121.0 (3)
C9A—C10A—H10A119.5C9B—C10B—H10B119.5
C11A—C10A—H10A119.5C11B—C10B—H10B119.5
C10A—C11A—C12A119.9 (3)C10B—C11B—C12B120.2 (3)
C10A—C11A—H11A120.0C10B—C11B—H11B119.9
C12A—C11A—H11A120.0C12B—C11B—H11B119.9
O2A—C12A—C11A124.9 (2)O2B—C12B—C11B125.0 (2)
O2A—C12A—C13A115.9 (2)O2B—C12B—C13B116.1 (2)
C11A—C12A—C13A119.2 (2)C11B—C12B—C13B118.9 (3)
O1A—C13A—C8A118.5 (2)O1B—C13B—C8B118.1 (2)
O1A—C13A—C12A120.9 (2)O1B—C13B—C12B120.9 (2)
C8A—C13A—C12A120.5 (2)C8B—C13B—C12B120.8 (2)
O1A—C14A—C15A107.6 (2)O1B—C14B—C15B107.4 (2)
O1A—C14A—H14A110.2O1B—C14B—H14C110.2
C15A—C14A—H14A110.2C15B—C14B—H14C110.2
O1A—C14A—H14B110.2O1B—C14B—H14D110.2
C15A—C14A—H14B110.2C15B—C14B—H14D110.2
H14A—C14A—H14B108.5H14C—C14B—H14D108.5
C16A—C15A—C20A118.7 (3)C20B—C15B—C16B118.9 (2)
C16A—C15A—C14A121.1 (2)C20B—C15B—C14B120.1 (2)
C20A—C15A—C14A120.1 (2)C16B—C15B—C14B121.0 (2)
C15A—C16A—C17A120.4 (3)C15B—C16B—C17B120.1 (3)
C15A—C16A—H16A119.8C15B—C16B—H16B119.9
C17A—C16A—H16A119.8C17B—C16B—H16B119.9
C18A—C17A—C16A119.9 (3)C18B—C17B—C16B120.1 (3)
C18A—C17A—H17A120.1C18B—C17B—H17B120.0
C16A—C17A—H17A120.1C16B—C17B—H17B120.0
C17A—C18A—C19A120.4 (3)C17B—C18B—C19B120.2 (3)
C17A—C18A—H18A119.8C17B—C18B—H18B119.9
C19A—C18A—H18A119.8C19B—C18B—H18B119.9
C18A—C19A—C20A119.5 (3)C20B—C19B—C18B119.7 (3)
C18A—C19A—H19A120.2C20B—C19B—H19B120.2
C20A—C19A—H19A120.2C18B—C19B—H19B120.2
C19A—C20A—C15A121.0 (3)C19B—C20B—C15B121.1 (3)
C19A—C20A—H20A119.5C19B—C20B—H20B119.5
C15A—C20A—H20A119.5C15B—C20B—H20B119.5
O2A—C21A—H21A109.5O2B—C21B—H21D109.5
O2A—C21A—H21B109.5O2B—C21B—H21E109.5
H21A—C21A—H21B109.5H21D—C21B—H21E109.5
O2A—C21A—H21C109.5O2B—C21B—H21F109.5
H21A—C21A—H21C109.5H21D—C21B—H21F109.5
H21B—C21A—H21C109.5H21E—C21B—H21F109.5
C6A—C1A—C2A—C3A−1.4 (5)C6B—C1B—C2B—C3B−0.3 (4)
C1A—C2A—C3A—C4A3.1 (5)C1B—C2B—C3B—C4B−0.7 (4)
C2A—C3A—C4A—C5A−1.9 (5)C2B—C3B—C4B—C5B0.4 (4)
C3A—C4A—C5A—N2A−175.4 (3)C3B—C4B—C5B—N2B177.2 (3)
C3A—C4A—C5A—C6A−1.0 (4)C3B—C4B—C5B—C6B0.8 (4)
C7A—N1A—C6A—C1A−30.8 (4)C2B—C1B—C6B—C5B1.5 (4)
C7A—N1A—C6A—C5A154.2 (3)C2B—C1B—C6B—N1B178.1 (3)
C2A—C1A—C6A—N1A−176.5 (3)N2B—C5B—C6B—C1B−178.2 (3)
C2A—C1A—C6A—C5A−1.6 (4)C4B—C5B—C6B—C1B−1.7 (4)
N2A—C5A—C6A—N1A−7.4 (4)N2B—C5B—C6B—N1B4.9 (4)
C4A—C5A—C6A—N1A178.1 (3)C4B—C5B—C6B—N1B−178.6 (2)
N2A—C5A—C6A—C1A177.2 (3)C7B—N1B—C6B—C1B33.0 (4)
C4A—C5A—C6A—C1A2.7 (4)C7B—N1B—C6B—C5B−150.3 (3)
C6A—N1A—C7A—C8A179.2 (2)C6B—N1B—C7B—C8B−178.7 (2)
N1A—C7A—C8A—C13A178.0 (3)N1B—C7B—C8B—C13B−179.1 (3)
N1A—C7A—C8A—C9A−1.7 (4)N1B—C7B—C8B—C9B−0.5 (4)
C13A—C8A—C9A—C10A0.8 (4)C13B—C8B—C9B—C10B−0.7 (4)
C7A—C8A—C9A—C10A−179.4 (3)C7B—C8B—C9B—C10B−179.3 (3)
C8A—C9A—C10A—C11A−1.3 (4)C8B—C9B—C10B—C11B0.8 (4)
C9A—C10A—C11A—C12A1.0 (4)C9B—C10B—C11B—C12B−0.4 (4)
C21A—O2A—C12A—C11A−3.6 (4)C21B—O2B—C12B—C11B−2.5 (4)
C21A—O2A—C12A—C13A177.3 (2)C21B—O2B—C12B—C13B176.8 (2)
C10A—C11A—C12A—O2A−179.3 (3)C10B—C11B—C12B—O2B179.1 (3)
C10A—C11A—C12A—C13A−0.1 (4)C10B—C11B—C12B—C13B−0.1 (4)
C14A—O1A—C13A—C8A119.4 (3)C14B—O1B—C13B—C8B−120.0 (3)
C14A—O1A—C13A—C12A−63.8 (3)C14B—O1B—C13B—C12B64.1 (3)
C9A—C8A—C13A—O1A176.9 (2)C9B—C8B—C13B—O1B−175.8 (2)
C7A—C8A—C13A—O1A−2.9 (4)C7B—C8B—C13B—O1B2.8 (4)
C9A—C8A—C13A—C12A0.0 (4)C9B—C8B—C13B—C12B0.1 (4)
C7A—C8A—C13A—C12A−179.7 (2)C7B—C8B—C13B—C12B178.7 (2)
O2A—C12A—C13A—O1A2.1 (4)O2B—C12B—C13B—O1B−3.2 (4)
C11A—C12A—C13A—O1A−177.1 (2)C11B—C12B—C13B—O1B176.1 (2)
O2A—C12A—C13A—C8A178.8 (2)O2B—C12B—C13B—C8B−179.0 (2)
C11A—C12A—C13A—C8A−0.4 (4)C11B—C12B—C13B—C8B0.3 (4)
C13A—O1A—C14A—C15A−156.0 (2)C13B—O1B—C14B—C15B155.0 (2)
O1A—C14A—C15A—C16A−102.4 (3)O1B—C14B—C15B—C20B−65.1 (3)
O1A—C14A—C15A—C20A76.5 (3)O1B—C14B—C15B—C16B113.6 (3)
C20A—C15A—C16A—C17A0.0 (4)C20B—C15B—C16B—C17B−0.1 (4)
C14A—C15A—C16A—C17A178.8 (2)C14B—C15B—C16B—C17B−178.8 (2)
C15A—C16A—C17A—C18A−1.5 (4)C15B—C16B—C17B—C18B1.5 (4)
C16A—C17A—C18A—C19A1.4 (4)C16B—C17B—C18B—C19B−1.7 (4)
C17A—C18A—C19A—C20A0.1 (4)C17B—C18B—C19B—C20B0.4 (4)
C18A—C19A—C20A—C15A−1.7 (4)C18B—C19B—C20B—C15B1.0 (4)
C16A—C15A—C20A—C19A1.6 (4)C16B—C15B—C20B—C19B−1.2 (4)
C14A—C15A—C20A—C19A−177.3 (2)C14B—C15B—C20B—C19B177.5 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2A—H2AC···N1A0.92 (3)2.31 (3)2.735 (4)108 (2)
N2A—H2AC···N2Bi0.92 (3)2.49 (3)3.229 (4)138 (3)
N2B—H2BC···N1B0.90 (2)2.29 (3)2.726 (3)109 (2)
C7A—H7A···O1A0.952.432.765 (3)101
C7B—H7B···O1B0.952.462.790 (3)100
C14A—H14A···O2A0.992.432.895 (3)108
C14B—H14D···O2B0.992.452.903 (3)107
C21A—H21C···Cg1ii0.982.963.511 (3)117
C21B—H21F···Cg2iii0.982.813.739 (3)159
C10A—H10A···Cg3ii0.952.603.500 (3)159
C21B—H21E···Cg4iv0.982.803.433 (3)123
C21A—H21B···Cg5v0.982.963.844 (4)150
C10B—H10B···Cg6iv0.952.663.587 (3)165
N2B—H2BC···Cg6vi0.90 (2)2.83 (3)3.288 (3)113 (2)

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+2, y−1/2, −z+1/2; (iii) x−1, y, z; (iv) −x+1, y+1/2, −z+1/2; (v) x+1, y, z; (vi) x, −y+1/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2609).

References

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