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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2994–o2995.
Published online 2010 October 31. doi:  10.1107/S1600536810043266
PMCID: PMC3009129

(1E,2E)-1,2-Bis[1-(2-methoxy­phen­yl)ethyl­idene]hydrazine1

Abstract

There are two crystallographically independent mol­ecules in the asymmetric unit of the title compound, C18H20N2O2. The two mol­ecules exist in an E,E configuration with respect to the two C=N double bonds. The dihedral angles between the two benzene rings in each mol­ecule are 16.89 (6) and 18.84 (6)°. In each mol­ecule, the two meth­oxy groups are coplanar with their attached benzene rings, with r.m.s. deviations of 0.0078 and 0.0336 Å in one mol­ecule, and 0.0163 and 0.0207 Å in the other. An intra­molecular C—H(...)O hydrogen bond is present in one mol­ecule. In the crystal structure, mol­ecules are arranged into ribbons along the c axis. These ribbons are further stacked along the a axis. The mol­ecules are consolidated by C(...)N [3.306 (2)–3.427 (2) Å] and C(...)O [3.3284 (16)–3.3863 (15) Å] short contacts. C—H(...)π inter­actions are also observed.

Related literature

For related structures, see: Jansrisewangwong et al. (2010 [triangle]); Zhao et al. (2006 [triangle]). For background to and biological activities of hydra­zones, see: El-Sherif (2009 [triangle]); Melnyk et al. (2006 [triangle]); Papakonstanti­nou-Garoufalias et al. (2002 [triangle]); Patole et al. (2003 [triangle]); Sridhar et al. (2002 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2994-scheme1.jpg

Experimental

Crystal data

  • C18H20N2O2
  • M r = 296.36
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2994-efi1.jpg
  • a = 7.9695 (2) Å
  • b = 14.8028 (4) Å
  • c = 15.4704 (4) Å
  • α = 117.909 (1)°
  • β = 90.151 (1)°
  • γ = 91.979 (1)°
  • V = 1611.46 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 100 K
  • 0.55 × 0.37 × 0.20 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.957, T max = 0.984
  • 39016 measured reflections
  • 9367 independent reflections
  • 7773 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.123
  • S = 1.02
  • 9367 reflections
  • 405 parameters
  • H-atom parameters constrained
  • Δρmax = 0.37 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; 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, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810043266/rz2497sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043266/rz2497Isup2.hkl

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

Acknowledgments

PJ thanks the Graduate School, Prince of Songkla University, for a graduate study research grant. The authors thank the Prince of Songkla University for financial support. The authors also thank Universiti Sains Malaysia for the research university grant No. 1001/PFIZIK/811160.

supplementary crystallographic information

Comment

Hydrazone derivatives play an important role in antimicrobial activity. Furthermore, a number of hydrazide and hydrazone derivatives have demonstrated to possess antibacterial, antifungal (Papakonstantinou-Garoufalias et al., 2002), anticonvulsant (Sridhar et al., 2002), anti-inflammatory (El-Sherif, 2009), antimalarial (Melnyk et al., 2006) and antituberculosis activities (Patole et al., 2003). These interesting features of hydrazones have led us to synthesize several hydrazone derivatives to study their antibacterial activities. Herein we report the synthesis and crystal structure of the title compound, (I).

There are two molecules (A and B) in an asymmetric unit of (I) (Fig. 1). The two molecules have slightly different bond angles but exist in the same configuration which is E,E configuration with respect to the C7═N1 and C8═N2 double bonds [1.2835 (14) and 1.2821 (14) Å, respectively in molecule A, and 1.2877 (14) and 1,2837 (13) Å in molecule B] and with torsion angles N2–N1–C7–C6 = 169.23 (9)° and N1–N2–C8–C9 = 167.25 (19)° in molecule A [-166.13 (9) and -166.24 (9)° in molecule B]. The dihedral angle between the two benzene rings is 16.89 (6)° in molecule A [18.84 (6)° in molecule B]. The two methoxy groups are co-planar with each attached benzene ring with the dihedral angles of C15–O1–C1–C2 = -3.00 (17)° and C18–O2–C14–C13 = 1.85 (15)° in molecule A [the corresponding values are 0.99 (16) and -1.54 (18)° in molecule B]. The two methyl groups are twisted from the plane of benzene rings and their orientations can be indicated by the torsion angles C1–C6–C7–C16 = -48.69 (14)° and C17–C8–C9–C14 = -49.33 (16)° in molecule A [the correspondibng values are 44.04 (16) and 53.67 (15)° in molecule B]. In molecule B, the intramolecular C17B—H17F···O2B weak interaction (Table 1) generate S(6) ring motif (Bernstein et al., 1995). The bond distances are of normal values (Allen et al., 1987) and are comparable with a related structure (Jansrisewangwong et al., 2010; Zhao et al., 2006).

In the crystal structure (Fig. 2), the molecules are arranged into ribbons along the c axis. These ribbons are further stacked along the a axis. The molecules are consolidated by C···N [3.306 (2)–3.427 (2) Å] and C···O [3.3284 (16)–3.3863 (15) Å] short contacts. C—H···π interactions were also observed (Table 1); Cg1 and Cg2 are the centroid of C9A–C14A and C1B–C6B rings, respectively.

Experimental

The title compound was synthesized by mixing a solution (1:2 molar ratio) of hydrazine hydrate (0.10 ml, 2 mmol) and 2-methoxyacetophenone (0.55 ml, 4 mmol) in ethanol (20 ml). The resulting solution was refluxed for 5 h, yielding the yellow crystalline solid. The resultant solid was filtered off and washed with methanol. Yellow block-shaped single crystals of the title compound suitable for x-ray structure determination were recrystalized from acetone by slow evaporation of the solvent at room temperature over several days.

Refinement

H atoms were positioned geometrically and allowed to ride on their parent atoms, with d(C—H) = 0.93 Å for aromatic and 0.96 Å for CH3 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 residual electron density peak is located at 0.69 Å from C7A and the deepest hole is located at 0.24 Å from H17D.

Figures

Fig. 1.
The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. Aromatic H atoms were omitted for clarify.
Fig. 2.
The crystal packing of the title compound viewed along the b axis.

Crystal data

C18H20N2O2Z = 4
Mr = 296.36F(000) = 632
Triclinic, P1Dx = 1.222 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.9695 (2) ÅCell parameters from 9367 reflections
b = 14.8028 (4) Åθ = 1.5–30.0°
c = 15.4704 (4) ŵ = 0.08 mm1
α = 117.909 (1)°T = 100 K
β = 90.151 (1)°Block, yellow
γ = 91.979 (1)°0.55 × 0.37 × 0.20 mm
V = 1611.46 (7) Å3

Data collection

Bruker APEXII CCD area-detector diffractometer9367 independent reflections
Radiation source: sealed tube7773 reflections with I > 2σ(I)
graphiteRint = 0.028
[var phi] and ω scansθmax = 30.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −11→11
Tmin = 0.957, Tmax = 0.984k = −20→20
39016 measured reflectionsl = −21→21

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0567P)2 + 0.6198P] where P = (Fo2 + 2Fc2)/3
9367 reflections(Δ/σ)max = 0.001
405 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = −0.24 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > 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)

xyzUiso*/Ueq
O1A0.75936 (11)0.36403 (6)0.20160 (6)0.02473 (18)
O2A0.05444 (11)0.30674 (7)0.43253 (6)0.02626 (18)
N1A0.46008 (11)0.14041 (7)0.17196 (6)0.01854 (18)
N2A0.37331 (11)0.12913 (7)0.24477 (7)0.01884 (18)
C1A0.78882 (13)0.27395 (9)0.12023 (8)0.0191 (2)
C2A0.88899 (15)0.26604 (10)0.04349 (9)0.0252 (2)
H2AA0.94230.32410.04600.030*
C3A0.90873 (16)0.17096 (11)−0.03661 (9)0.0293 (3)
H3AA0.97650.1655−0.08750.035*
C4A0.82876 (17)0.08417 (10)−0.04166 (9)0.0288 (3)
H4AA0.84340.0206−0.09530.035*
C5A0.72626 (14)0.09266 (9)0.03416 (8)0.0217 (2)
H5AA0.67010.03460.02990.026*
C6A0.70634 (12)0.18658 (8)0.11623 (7)0.01635 (19)
C7A0.60121 (13)0.19120 (8)0.19741 (7)0.01595 (19)
C8A0.22915 (13)0.16892 (9)0.26668 (8)0.0194 (2)
C9A0.12412 (13)0.13672 (9)0.32803 (8)0.0201 (2)
C10A0.11483 (15)0.03358 (10)0.30463 (8)0.0251 (2)
H10A0.1765−0.01250.25270.030*
C11A0.01548 (16)−0.00223 (11)0.35703 (9)0.0297 (3)
H11A0.0111−0.07130.34040.036*
C12A−0.07677 (15)0.06652 (11)0.43420 (9)0.0295 (3)
H12A−0.14520.04310.46870.035*
C13A−0.06803 (14)0.16999 (11)0.46046 (9)0.0261 (2)
H13A−0.12950.21560.51280.031*
C14A0.03324 (13)0.20564 (10)0.40820 (8)0.0217 (2)
C15A0.8430 (2)0.45433 (11)0.20980 (12)0.0457 (4)
H15A0.81640.51150.27100.069*
H15B0.80700.46640.15700.069*
H15C0.96210.44600.20690.069*
C16A0.66645 (14)0.24582 (9)0.30146 (8)0.0200 (2)
H16A0.66530.19900.32830.030*
H16B0.59640.30180.33950.030*
H16C0.77930.27150.30300.030*
C17A0.15991 (16)0.23508 (12)0.22654 (10)0.0323 (3)
H17A0.18050.20510.15770.048*
H17B0.21380.30200.25920.048*
H17C0.04120.24040.23700.048*
C18A−0.0294 (2)0.37775 (12)0.51799 (10)0.0364 (3)
H18A0.00570.44630.53310.055*
H18B−0.00150.36580.57210.055*
H18C−0.14860.36870.50610.055*
O1B0.45456 (11)0.82808 (7)0.44885 (6)0.02682 (19)
O2B−0.27309 (11)0.85346 (6)0.18823 (6)0.02520 (18)
N1B0.11694 (11)0.64386 (7)0.25137 (7)0.01901 (18)
N2B0.03346 (11)0.65363 (7)0.17709 (7)0.01845 (18)
C1B0.46224 (13)0.72673 (10)0.42254 (8)0.0221 (2)
C2B0.55967 (14)0.68929 (11)0.47331 (9)0.0259 (2)
H2BA0.62620.73440.52660.031*
C3B0.55744 (16)0.58569 (11)0.44459 (9)0.0311 (3)
H3BA0.62350.56150.47840.037*
C4B0.45791 (18)0.51747 (11)0.36600 (10)0.0323 (3)
H4BA0.45550.44790.34740.039*
C5B0.36140 (15)0.55442 (10)0.31511 (9)0.0262 (2)
H5BA0.29440.50870.26240.031*
C6B0.36273 (13)0.65829 (9)0.34121 (8)0.0204 (2)
C7B0.26160 (13)0.69058 (9)0.27974 (8)0.0192 (2)
C8B−0.11241 (12)0.69174 (8)0.19615 (7)0.01565 (19)
C9B−0.21463 (12)0.67896 (8)0.10995 (7)0.01684 (19)
C10B−0.23044 (14)0.58243 (9)0.02918 (8)0.0219 (2)
H10B−0.17320.52870.02910.026*
C11B−0.33037 (16)0.56475 (10)−0.05160 (9)0.0290 (3)
H11B−0.34200.4995−0.10450.035*
C12B−0.41238 (16)0.64566 (11)−0.05217 (9)0.0313 (3)
H12B−0.47860.6344−0.10610.038*
C13B−0.39686 (15)0.74310 (10)0.02671 (9)0.0274 (3)
H13B−0.45150.79690.02530.033*
C14B−0.29881 (13)0.75991 (9)0.10809 (8)0.0196 (2)
C15B0.5555 (2)0.89710 (12)0.53241 (11)0.0390 (3)
H15D0.53250.96640.54840.058*
H15E0.67220.88560.51760.058*
H15F0.52930.88550.58700.058*
C16B0.33209 (15)0.76471 (12)0.24739 (10)0.0311 (3)
H16D0.30330.74080.17970.047*
H16E0.45210.77030.25580.047*
H16F0.28610.83050.28600.047*
C17B−0.18961 (14)0.73647 (9)0.29538 (8)0.0216 (2)
H17D−0.10330.75260.34440.032*
H17E−0.26960.68770.29780.032*
H17F−0.24530.79760.30740.032*
C18B−0.3482 (2)0.93885 (11)0.18693 (12)0.0457 (4)
H18D−0.31970.99970.24660.069*
H18E−0.46800.92770.18090.069*
H18F−0.30740.94670.13240.069*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1A0.0321 (4)0.0190 (4)0.0229 (4)−0.0043 (3)0.0011 (3)0.0100 (3)
O2A0.0248 (4)0.0347 (5)0.0257 (4)0.0080 (3)0.0060 (3)0.0190 (4)
N1A0.0171 (4)0.0241 (5)0.0169 (4)0.0001 (3)0.0025 (3)0.0117 (4)
N2A0.0171 (4)0.0243 (5)0.0175 (4)−0.0023 (3)0.0010 (3)0.0120 (4)
C1A0.0180 (5)0.0228 (5)0.0178 (5)−0.0019 (4)−0.0019 (4)0.0109 (4)
C2A0.0238 (5)0.0316 (6)0.0239 (5)−0.0085 (5)−0.0002 (4)0.0167 (5)
C3A0.0278 (6)0.0402 (7)0.0209 (5)−0.0039 (5)0.0068 (4)0.0155 (5)
C4A0.0332 (6)0.0304 (6)0.0192 (5)−0.0004 (5)0.0076 (5)0.0086 (5)
C5A0.0242 (5)0.0225 (5)0.0186 (5)−0.0013 (4)0.0029 (4)0.0098 (4)
C6A0.0143 (4)0.0211 (5)0.0159 (4)−0.0002 (4)−0.0001 (3)0.0105 (4)
C7A0.0160 (4)0.0183 (5)0.0159 (4)0.0028 (4)0.0020 (3)0.0098 (4)
C8A0.0160 (4)0.0285 (6)0.0170 (5)−0.0019 (4)−0.0010 (4)0.0136 (4)
C9A0.0138 (4)0.0330 (6)0.0178 (5)−0.0029 (4)−0.0017 (3)0.0156 (4)
C10A0.0235 (5)0.0328 (6)0.0191 (5)−0.0060 (5)−0.0015 (4)0.0128 (5)
C11A0.0303 (6)0.0353 (7)0.0271 (6)−0.0111 (5)−0.0030 (5)0.0185 (5)
C12A0.0226 (5)0.0480 (8)0.0264 (6)−0.0080 (5)−0.0009 (4)0.0250 (6)
C13A0.0166 (5)0.0458 (7)0.0221 (5)0.0020 (5)0.0026 (4)0.0209 (5)
C14A0.0146 (4)0.0357 (6)0.0211 (5)0.0014 (4)−0.0012 (4)0.0184 (5)
C15A0.0716 (11)0.0246 (7)0.0364 (8)−0.0172 (7)0.0054 (7)0.0116 (6)
C16A0.0192 (5)0.0259 (5)0.0167 (5)−0.0003 (4)−0.0003 (4)0.0115 (4)
C17A0.0230 (6)0.0553 (9)0.0363 (7)0.0105 (5)0.0073 (5)0.0355 (7)
C18A0.0446 (8)0.0412 (8)0.0298 (6)0.0173 (6)0.0119 (6)0.0207 (6)
O1B0.0247 (4)0.0356 (5)0.0264 (4)−0.0053 (3)−0.0075 (3)0.0201 (4)
O2B0.0325 (4)0.0206 (4)0.0231 (4)0.0069 (3)−0.0027 (3)0.0103 (3)
N1B0.0166 (4)0.0256 (5)0.0178 (4)0.0042 (3)−0.0004 (3)0.0124 (4)
N2B0.0162 (4)0.0246 (5)0.0176 (4)0.0013 (3)−0.0015 (3)0.0124 (4)
C1B0.0136 (4)0.0387 (6)0.0210 (5)0.0017 (4)0.0019 (4)0.0197 (5)
C2B0.0162 (5)0.0473 (7)0.0215 (5)0.0029 (5)−0.0004 (4)0.0220 (5)
C3B0.0276 (6)0.0490 (8)0.0256 (6)0.0146 (5)0.0020 (5)0.0241 (6)
C4B0.0372 (7)0.0367 (7)0.0278 (6)0.0158 (6)0.0020 (5)0.0182 (5)
C5B0.0261 (6)0.0343 (6)0.0202 (5)0.0103 (5)0.0016 (4)0.0138 (5)
C6B0.0134 (4)0.0346 (6)0.0180 (5)0.0057 (4)0.0027 (4)0.0160 (4)
C7B0.0144 (4)0.0299 (6)0.0172 (5)0.0042 (4)0.0014 (3)0.0141 (4)
C8B0.0150 (4)0.0179 (5)0.0161 (4)−0.0010 (4)−0.0012 (3)0.0098 (4)
C9B0.0134 (4)0.0228 (5)0.0168 (4)0.0009 (4)−0.0005 (3)0.0113 (4)
C10B0.0230 (5)0.0244 (5)0.0181 (5)0.0027 (4)−0.0012 (4)0.0097 (4)
C11B0.0328 (6)0.0310 (6)0.0184 (5)0.0019 (5)−0.0058 (4)0.0076 (5)
C12B0.0299 (6)0.0427 (7)0.0203 (5)0.0069 (5)−0.0065 (4)0.0135 (5)
C13B0.0263 (6)0.0357 (7)0.0234 (5)0.0100 (5)−0.0021 (4)0.0160 (5)
C14B0.0182 (5)0.0239 (5)0.0183 (5)0.0035 (4)0.0009 (4)0.0112 (4)
C15B0.0461 (8)0.0438 (8)0.0347 (7)−0.0164 (6)−0.0191 (6)0.0262 (7)
C16B0.0189 (5)0.0542 (8)0.0363 (7)−0.0069 (5)−0.0063 (5)0.0354 (7)
C17B0.0206 (5)0.0295 (6)0.0180 (5)0.0055 (4)0.0025 (4)0.0135 (4)
C18B0.0700 (11)0.0272 (7)0.0393 (8)0.0196 (7)−0.0090 (7)0.0140 (6)

Geometric parameters (Å, °)

O1A—C1A1.3673 (14)O1B—C1B1.3619 (15)
O1A—C15A1.4237 (16)O1B—C15B1.4366 (16)
O2A—C14A1.3656 (15)O2B—C14B1.3670 (14)
O2A—C18A1.4325 (15)O2B—C18B1.4255 (15)
N1A—C7A1.2835 (14)N1B—C7B1.2877 (14)
N1A—N2A1.3954 (12)N1B—N2B1.3938 (12)
N2A—C8A1.2821 (14)N2B—C8B1.2837 (13)
C1A—C2A1.3935 (15)C1B—C2B1.4004 (15)
C1A—C6A1.4053 (15)C1B—C6B1.4086 (16)
C2A—C3A1.3875 (18)C2B—C3B1.382 (2)
C2A—H2AA0.9300C2B—H2BA0.9300
C3A—C4A1.3828 (19)C3B—C4B1.385 (2)
C3A—H3AA0.9300C3B—H3BA0.9300
C4A—C5A1.3904 (16)C4B—C5B1.3926 (16)
C4A—H4AA0.9300C4B—H4BA0.9300
C5A—C6A1.3906 (15)C5B—C6B1.3946 (18)
C5A—H5AA0.9300C5B—H5BA0.9300
C6A—C7A1.4876 (14)C6B—C7B1.4935 (14)
C7A—C16A1.5044 (14)C7B—C16B1.4977 (17)
C8A—C9A1.4929 (15)C8B—C9B1.4917 (13)
C8A—C17A1.5013 (16)C8B—C17B1.5018 (14)
C9A—C10A1.3935 (17)C9B—C10B1.3907 (15)
C9A—C14A1.4052 (16)C9B—C14B1.4052 (15)
C10A—C11A1.3936 (17)C10B—C11B1.3924 (15)
C10A—H10A0.9300C10B—H10B0.9300
C11A—C12A1.3858 (19)C11B—C12B1.3876 (18)
C11A—H11A0.9300C11B—H11B0.9300
C12A—C13A1.388 (2)C12B—C13B1.3870 (18)
C12A—H12A0.9300C12B—H12B0.9300
C13A—C14A1.3990 (16)C13B—C14B1.3948 (15)
C13A—H13A0.9300C13B—H13B0.9300
C15A—H15A0.9600C15B—H15D0.9600
C15A—H15B0.9600C15B—H15E0.9600
C15A—H15C0.9600C15B—H15F0.9600
C16A—H16A0.9600C16B—H16D0.9600
C16A—H16B0.9600C16B—H16E0.9600
C16A—H16C0.9600C16B—H16F0.9600
C17A—H17A0.9600C17B—H17D0.9600
C17A—H17B0.9600C17B—H17E0.9600
C17A—H17C0.9600C17B—H17F0.9600
C18A—H18A0.9600C18B—H18D0.9600
C18A—H18B0.9600C18B—H18E0.9600
C18A—H18C0.9600C18B—H18F0.9600
C1A—O1A—C15A117.43 (10)C1B—O1B—C15B116.31 (10)
C14A—O2A—C18A116.57 (10)C14B—O2B—C18B117.64 (10)
C7A—N1A—N2A116.67 (9)C7B—N1B—N2B116.99 (9)
C8A—N2A—N1A116.75 (9)C8B—N2B—N1B117.11 (9)
O1A—C1A—C2A124.13 (10)O1B—C1B—C2B123.31 (11)
O1A—C1A—C6A115.45 (9)O1B—C1B—C6B116.88 (9)
C2A—C1A—C6A120.40 (10)C2B—C1B—C6B119.79 (12)
C3A—C2A—C1A119.57 (11)C3B—C2B—C1B120.34 (12)
C3A—C2A—H2AA120.2C3B—C2B—H2BA119.8
C1A—C2A—H2AA120.2C1B—C2B—H2BA119.8
C4A—C3A—C2A120.79 (11)C2B—C3B—C4B120.68 (11)
C4A—C3A—H3AA119.6C2B—C3B—H3BA119.7
C2A—C3A—H3AA119.6C4B—C3B—H3BA119.7
C3A—C4A—C5A119.47 (11)C3B—C4B—C5B119.11 (13)
C3A—C4A—H4AA120.3C3B—C4B—H4BA120.4
C5A—C4A—H4AA120.3C5B—C4B—H4BA120.4
C4A—C5A—C6A121.10 (11)C4B—C5B—C6B121.66 (12)
C4A—C5A—H5AA119.4C4B—C5B—H5BA119.2
C6A—C5A—H5AA119.4C6B—C5B—H5BA119.2
C5A—C6A—C1A118.64 (10)C5B—C6B—C1B118.39 (10)
C5A—C6A—C7A119.18 (10)C5B—C6B—C7B118.06 (10)
C1A—C6A—C7A122.16 (9)C1B—C6B—C7B123.53 (11)
N1A—C7A—C6A115.93 (9)N1B—C7B—C6B114.65 (10)
N1A—C7A—C16A123.32 (9)N1B—C7B—C16B123.60 (9)
C6A—C7A—C16A120.57 (9)C6B—C7B—C16B121.53 (9)
N2A—C8A—C9A115.31 (10)N2B—C8B—C9B115.69 (9)
N2A—C8A—C17A123.59 (10)N2B—C8B—C17B124.37 (9)
C9A—C8A—C17A120.83 (9)C9B—C8B—C17B119.59 (9)
C10A—C9A—C14A118.35 (10)C10B—C9B—C14B118.76 (9)
C10A—C9A—C8A118.65 (10)C10B—C9B—C8B118.58 (9)
C14A—C9A—C8A123.00 (11)C14B—C9B—C8B122.64 (10)
C9A—C10A—C11A121.69 (12)C9B—C10B—C11B121.21 (11)
C9A—C10A—H10A119.2C9B—C10B—H10B119.4
C11A—C10A—H10A119.2C11B—C10B—H10B119.4
C12A—C11A—C10A119.09 (13)C12B—C11B—C10B119.19 (11)
C12A—C11A—H11A120.5C12B—C11B—H11B120.4
C10A—C11A—H11A120.5C10B—C11B—H11B120.4
C11A—C12A—C13A120.65 (11)C13B—C12B—C11B120.86 (11)
C11A—C12A—H12A119.7C13B—C12B—H12B119.6
C13A—C12A—H12A119.7C11B—C12B—H12B119.6
C12A—C13A—C14A120.00 (11)C12B—C13B—C14B119.64 (11)
C12A—C13A—H13A120.0C12B—C13B—H13B120.2
C14A—C13A—H13A120.0C14B—C13B—H13B120.2
O2A—C14A—C13A123.34 (11)O2B—C14B—C13B123.88 (10)
O2A—C14A—C9A116.44 (10)O2B—C14B—C9B115.77 (9)
C13A—C14A—C9A120.19 (12)C13B—C14B—C9B120.31 (11)
O1A—C15A—H15A109.5O1B—C15B—H15D109.5
O1A—C15A—H15B109.5O1B—C15B—H15E109.5
H15A—C15A—H15B109.5H15D—C15B—H15E109.5
O1A—C15A—H15C109.5O1B—C15B—H15F109.5
H15A—C15A—H15C109.5H15D—C15B—H15F109.5
H15B—C15A—H15C109.5H15E—C15B—H15F109.5
C7A—C16A—H16A109.5C7B—C16B—H16D109.5
C7A—C16A—H16B109.5C7B—C16B—H16E109.5
H16A—C16A—H16B109.5H16D—C16B—H16E109.5
C7A—C16A—H16C109.5C7B—C16B—H16F109.5
H16A—C16A—H16C109.5H16D—C16B—H16F109.5
H16B—C16A—H16C109.5H16E—C16B—H16F109.5
C8A—C17A—H17A109.5C8B—C17B—H17D109.5
C8A—C17A—H17B109.5C8B—C17B—H17E109.5
H17A—C17A—H17B109.5H17D—C17B—H17E109.5
C8A—C17A—H17C109.5C8B—C17B—H17F109.5
H17A—C17A—H17C109.5H17D—C17B—H17F109.5
H17B—C17A—H17C109.5H17E—C17B—H17F109.5
O2A—C18A—H18A109.5O2B—C18B—H18D109.5
O2A—C18A—H18B109.5O2B—C18B—H18E109.5
H18A—C18A—H18B109.5H18D—C18B—H18E109.5
O2A—C18A—H18C109.5O2B—C18B—H18F109.5
H18A—C18A—H18C109.5H18D—C18B—H18F109.5
H18B—C18A—H18C109.5H18E—C18B—H18F109.5
C7A—N1A—N2A—C8A117.39 (11)C7B—N1B—N2B—C8B−121.46 (11)
C15A—O1A—C1A—C2A−3.00 (17)C15B—O1B—C1B—C2B0.99 (16)
C15A—O1A—C1A—C6A178.73 (12)C15B—O1B—C1B—C6B179.48 (11)
O1A—C1A—C2A—C3A−179.01 (11)O1B—C1B—C2B—C3B177.84 (11)
C6A—C1A—C2A—C3A−0.82 (17)C6B—C1B—C2B—C3B−0.61 (16)
C1A—C2A—C3A—C4A0.69 (19)C1B—C2B—C3B—C4B−0.64 (18)
C2A—C3A—C4A—C5A0.6 (2)C2B—C3B—C4B—C5B0.9 (2)
C3A—C4A—C5A—C6A−1.75 (19)C3B—C4B—C5B—C6B0.11 (19)
C4A—C5A—C6A—C1A1.61 (16)C4B—C5B—C6B—C1B−1.33 (17)
C4A—C5A—C6A—C7A−177.40 (10)C4B—C5B—C6B—C7B177.19 (11)
O1A—C1A—C6A—C5A178.03 (9)O1B—C1B—C6B—C5B−176.99 (10)
C2A—C1A—C6A—C5A−0.31 (15)C2B—C1B—C6B—C5B1.56 (16)
O1A—C1A—C6A—C7A−2.99 (14)O1B—C1B—C6B—C7B4.58 (15)
C2A—C1A—C6A—C7A178.67 (10)C2B—C1B—C6B—C7B−176.86 (10)
N2A—N1A—C7A—C6A169.23 (9)N2B—N1B—C7B—C6B−166.13 (9)
N2A—N1A—C7A—C16A−5.92 (15)N2B—N1B—C7B—C16B8.60 (16)
C5A—C6A—C7A—N1A−45.02 (14)C5B—C6B—C7B—N1B40.45 (14)
C1A—C6A—C7A—N1A136.01 (11)C1B—C6B—C7B—N1B−141.12 (11)
C5A—C6A—C7A—C16A130.28 (11)C5B—C6B—C7B—C16B−134.40 (12)
C1A—C6A—C7A—C16A−48.69 (14)C1B—C6B—C7B—C16B44.04 (16)
N1A—N2A—C8A—C9A167.25 (9)N1B—N2B—C8B—C9B−166.24 (9)
N1A—N2A—C8A—C17A−6.81 (17)N1B—N2B—C8B—C17B6.97 (16)
N2A—C8A—C9A—C10A−43.91 (14)N2B—C8B—C9B—C10B48.84 (14)
C17A—C8A—C9A—C10A130.33 (12)C17B—C8B—C9B—C10B−124.72 (11)
N2A—C8A—C9A—C14A136.44 (11)N2B—C8B—C9B—C14B−132.77 (11)
C17A—C8A—C9A—C14A−49.33 (16)C17B—C8B—C9B—C14B53.67 (15)
C14A—C9A—C10A—C11A1.51 (16)C14B—C9B—C10B—C11B−1.41 (17)
C8A—C9A—C10A—C11A−178.16 (10)C8B—C9B—C10B—C11B177.04 (11)
C9A—C10A—C11A—C12A0.19 (18)C9B—C10B—C11B—C12B1.50 (19)
C10A—C11A—C12A—C13A−1.31 (18)C10B—C11B—C12B—C13B−0.5 (2)
C11A—C12A—C13A—C14A0.68 (18)C11B—C12B—C13B—C14B−0.6 (2)
C18A—O2A—C14A—C13A1.85 (15)C18B—O2B—C14B—C13B−1.54 (18)
C18A—O2A—C14A—C9A−176.08 (10)C18B—O2B—C14B—C9B176.41 (12)
C12A—C13A—C14A—O2A−176.79 (10)C12B—C13B—C14B—O2B178.53 (12)
C12A—C13A—C14A—C9A1.07 (16)C12B—C13B—C14B—C9B0.67 (18)
C10A—C9A—C14A—O2A175.87 (9)C10B—C9B—C14B—O2B−177.71 (10)
C8A—C9A—C14A—O2A−4.47 (15)C8B—C9B—C14B—O2B3.90 (15)
C10A—C9A—C14A—C13A−2.13 (15)C10B—C9B—C14B—C13B0.32 (16)
C8A—C9A—C14A—C13A177.52 (10)C8B—C9B—C14B—C13B−178.07 (10)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C17B—H17F···O2B0.962.362.9918 (17)123
C15B—H15E···Cg1i0.962.833.5974 (17)138
C18A—H18C···Cg2ii0.962.903.6976 (17)141

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

Footnotes

1This paper is dedicated to the late His Majesty King Chulalongkorn (King Rama V) of Thailand for his numerous reforms to modernize the country on the occasion of Chulalongkorn Day (Piyamaharaj Day) which fell on the 23rd October.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2497).

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