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

Chantrapromma, S.; Jansrisewangwong, P.; Fun, H.-K.

doi:10.1107/S1600536810043266

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 11| November 2010| Pages o2994-o2995

https://doi.org/10.1107/S1600536810043266

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

Suchada Chantrapromma,^a ^*‡ Patcharaporn Jansrisewangwong ^a and Hoong-Kun Fun ^b §

^aCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: suchada.c@psu.ac.th

(Received 2 October 2010; accepted 23 October 2010; online 31 October 2010)

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

Experimental

Crystal data

C₁₈H₂₀N₂O₂
M_r = 296.36
Triclinic, $[P \overline 1]$
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 ) 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[F² > 2σ(F²)] = 0.046
wR(F²) = 0.123
S = 1.02
9367 reflections
405 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17B—H17F⋯O2B	0.96	2.36	2.9918 (17)	123
C15B—H15E⋯Cg1ⁱ	0.96	2.83	3.5974 (17)	138
C18A—H18C⋯Cg2ⁱⁱ	0.96	2.90	3.6976 (17)	141
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1. Cg1 and Cg2 are the centroids of the C9A–C14A and C1B–C6B rings, respectively.

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

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810043266/rz2497Isup2.hkl

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	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.

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

Crystal data top

C₁₈H₂₀N₂O₂	Z = 4
M_r = 296.36	F(000) = 632
Triclinic, P1	D_x = 1.222 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9695 (2) Å	Cell parameters from 9367 reflections
b = 14.8028 (4) Å	θ = 1.5–30.0°
c = 15.4704 (4) Å	µ = 0.08 mm⁻¹
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 top

Bruker APEXII CCD area-detector diffractometer	9367 independent reflections
Radiation source: sealed tube	7773 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
φ and ω scans	θ_max = 30.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
T_min = 0.957, T_max = 0.984	k = −20→20
39016 measured reflections	l = −21→21

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0567P)² + 0.6198P] where P = (F_o² + 2F_c²)/3
9367 reflections	(Δ/σ)_max = 0.001
405 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₈H₂₀N₂O₂	γ = 91.979 (1)°
M_r = 296.36	V = 1611.46 (7) Å³
Triclinic, P1	Z = 4
a = 7.9695 (2) Å	Mo Kα radiation
b = 14.8028 (4) Å	µ = 0.08 mm⁻¹
c = 15.4704 (4) Å	T = 100 K
α = 117.909 (1)°	0.55 × 0.37 × 0.20 mm
β = 90.151 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	9367 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	7773 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.984	R_int = 0.028
39016 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.02	Δρ_max = 0.37 e Å⁻³
9367 reflections	Δρ_min = −0.24 e Å⁻³
405 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
O1A	0.75936 (11)	0.36403 (6)	0.20160 (6)	0.02473 (18)
O2A	0.05444 (11)	0.30674 (7)	0.43253 (6)	0.02626 (18)
N1A	0.46008 (11)	0.14041 (7)	0.17196 (6)	0.01854 (18)
N2A	0.37331 (11)	0.12913 (7)	0.24477 (7)	0.01884 (18)
C1A	0.78882 (13)	0.27395 (9)	0.12023 (8)	0.0191 (2)
C2A	0.88899 (15)	0.26604 (10)	0.04349 (9)	0.0252 (2)
H2AA	0.9423	0.3241	0.0460	0.030*
C3A	0.90873 (16)	0.17096 (11)	−0.03661 (9)	0.0293 (3)
H3AA	0.9765	0.1655	−0.0875	0.035*
C4A	0.82876 (17)	0.08417 (10)	−0.04166 (9)	0.0288 (3)
H4AA	0.8434	0.0206	−0.0953	0.035*
C5A	0.72626 (14)	0.09266 (9)	0.03416 (8)	0.0217 (2)
H5AA	0.6701	0.0346	0.0299	0.026*
C6A	0.70634 (12)	0.18658 (8)	0.11623 (7)	0.01635 (19)
C7A	0.60121 (13)	0.19120 (8)	0.19741 (7)	0.01595 (19)
C8A	0.22915 (13)	0.16892 (9)	0.26668 (8)	0.0194 (2)
C9A	0.12412 (13)	0.13672 (9)	0.32803 (8)	0.0201 (2)
C10A	0.11483 (15)	0.03358 (10)	0.30463 (8)	0.0251 (2)
H10A	0.1765	−0.0125	0.2527	0.030*
C11A	0.01548 (16)	−0.00223 (11)	0.35703 (9)	0.0297 (3)
H11A	0.0111	−0.0713	0.3404	0.036*
C12A	−0.07677 (15)	0.06652 (11)	0.43420 (9)	0.0295 (3)
H12A	−0.1452	0.0431	0.4687	0.035*
C13A	−0.06803 (14)	0.16999 (11)	0.46046 (9)	0.0261 (2)
H13A	−0.1295	0.2156	0.5128	0.031*
C14A	0.03324 (13)	0.20564 (10)	0.40820 (8)	0.0217 (2)
C15A	0.8430 (2)	0.45433 (11)	0.20980 (12)	0.0457 (4)
H15A	0.8164	0.5115	0.2710	0.069*
H15B	0.8070	0.4664	0.1570	0.069*
H15C	0.9621	0.4460	0.2069	0.069*
C16A	0.66645 (14)	0.24582 (9)	0.30146 (8)	0.0200 (2)
H16A	0.6653	0.1990	0.3283	0.030*
H16B	0.5964	0.3018	0.3395	0.030*
H16C	0.7793	0.2715	0.3030	0.030*
C17A	0.15991 (16)	0.23508 (12)	0.22654 (10)	0.0323 (3)
H17A	0.1805	0.2051	0.1577	0.048*
H17B	0.2138	0.3020	0.2592	0.048*
H17C	0.0412	0.2404	0.2370	0.048*
C18A	−0.0294 (2)	0.37775 (12)	0.51799 (10)	0.0364 (3)
H18A	0.0057	0.4463	0.5331	0.055*
H18B	−0.0015	0.3658	0.5721	0.055*
H18C	−0.1486	0.3687	0.5061	0.055*
O1B	0.45456 (11)	0.82808 (7)	0.44885 (6)	0.02682 (19)
O2B	−0.27309 (11)	0.85346 (6)	0.18823 (6)	0.02520 (18)
N1B	0.11694 (11)	0.64386 (7)	0.25137 (7)	0.01901 (18)
N2B	0.03346 (11)	0.65363 (7)	0.17709 (7)	0.01845 (18)
C1B	0.46224 (13)	0.72673 (10)	0.42254 (8)	0.0221 (2)
C2B	0.55967 (14)	0.68929 (11)	0.47331 (9)	0.0259 (2)
H2BA	0.6262	0.7344	0.5266	0.031*
C3B	0.55744 (16)	0.58569 (11)	0.44459 (9)	0.0311 (3)
H3BA	0.6235	0.5615	0.4784	0.037*
C4B	0.45791 (18)	0.51747 (11)	0.36600 (10)	0.0323 (3)
H4BA	0.4555	0.4479	0.3474	0.039*
C5B	0.36140 (15)	0.55442 (10)	0.31511 (9)	0.0262 (2)
H5BA	0.2944	0.5087	0.2624	0.031*
C6B	0.36273 (13)	0.65829 (9)	0.34121 (8)	0.0204 (2)
C7B	0.26160 (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	−0.1732	0.5287	0.0291	0.026*
C11B	−0.33037 (16)	0.56475 (10)	−0.05160 (9)	0.0290 (3)
H11B	−0.3420	0.4995	−0.1045	0.035*
C12B	−0.41238 (16)	0.64566 (11)	−0.05217 (9)	0.0313 (3)
H12B	−0.4786	0.6344	−0.1061	0.038*
C13B	−0.39686 (15)	0.74310 (10)	0.02671 (9)	0.0274 (3)
H13B	−0.4515	0.7969	0.0253	0.033*
C14B	−0.29881 (13)	0.75991 (9)	0.10809 (8)	0.0196 (2)
C15B	0.5555 (2)	0.89710 (12)	0.53241 (11)	0.0390 (3)
H15D	0.5325	0.9664	0.5484	0.058*
H15E	0.6722	0.8856	0.5176	0.058*
H15F	0.5293	0.8855	0.5870	0.058*
C16B	0.33209 (15)	0.76471 (12)	0.24739 (10)	0.0311 (3)
H16D	0.3033	0.7408	0.1797	0.047*
H16E	0.4521	0.7703	0.2558	0.047*
H16F	0.2861	0.8305	0.2860	0.047*
C17B	−0.18961 (14)	0.73647 (9)	0.29538 (8)	0.0216 (2)
H17D	−0.1033	0.7526	0.3444	0.032*
H17E	−0.2696	0.6877	0.2978	0.032*
H17F	−0.2453	0.7976	0.3074	0.032*
C18B	−0.3482 (2)	0.93885 (11)	0.18693 (12)	0.0457 (4)
H18D	−0.3197	0.9997	0.2466	0.069*
H18E	−0.4680	0.9277	0.1809	0.069*
H18F	−0.3074	0.9467	0.1324	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0321 (4)	0.0190 (4)	0.0229 (4)	−0.0043 (3)	0.0011 (3)	0.0100 (3)
O2A	0.0248 (4)	0.0347 (5)	0.0257 (4)	0.0080 (3)	0.0060 (3)	0.0190 (4)
N1A	0.0171 (4)	0.0241 (5)	0.0169 (4)	0.0001 (3)	0.0025 (3)	0.0117 (4)
N2A	0.0171 (4)	0.0243 (5)	0.0175 (4)	−0.0023 (3)	0.0010 (3)	0.0120 (4)
C1A	0.0180 (5)	0.0228 (5)	0.0178 (5)	−0.0019 (4)	−0.0019 (4)	0.0109 (4)
C2A	0.0238 (5)	0.0316 (6)	0.0239 (5)	−0.0085 (5)	−0.0002 (4)	0.0167 (5)
C3A	0.0278 (6)	0.0402 (7)	0.0209 (5)	−0.0039 (5)	0.0068 (4)	0.0155 (5)
C4A	0.0332 (6)	0.0304 (6)	0.0192 (5)	−0.0004 (5)	0.0076 (5)	0.0086 (5)
C5A	0.0242 (5)	0.0225 (5)	0.0186 (5)	−0.0013 (4)	0.0029 (4)	0.0098 (4)
C6A	0.0143 (4)	0.0211 (5)	0.0159 (4)	−0.0002 (4)	−0.0001 (3)	0.0105 (4)
C7A	0.0160 (4)	0.0183 (5)	0.0159 (4)	0.0028 (4)	0.0020 (3)	0.0098 (4)
C8A	0.0160 (4)	0.0285 (6)	0.0170 (5)	−0.0019 (4)	−0.0010 (4)	0.0136 (4)
C9A	0.0138 (4)	0.0330 (6)	0.0178 (5)	−0.0029 (4)	−0.0017 (3)	0.0156 (4)
C10A	0.0235 (5)	0.0328 (6)	0.0191 (5)	−0.0060 (5)	−0.0015 (4)	0.0128 (5)
C11A	0.0303 (6)	0.0353 (7)	0.0271 (6)	−0.0111 (5)	−0.0030 (5)	0.0185 (5)
C12A	0.0226 (5)	0.0480 (8)	0.0264 (6)	−0.0080 (5)	−0.0009 (4)	0.0250 (6)
C13A	0.0166 (5)	0.0458 (7)	0.0221 (5)	0.0020 (5)	0.0026 (4)	0.0209 (5)
C14A	0.0146 (4)	0.0357 (6)	0.0211 (5)	0.0014 (4)	−0.0012 (4)	0.0184 (5)
C15A	0.0716 (11)	0.0246 (7)	0.0364 (8)	−0.0172 (7)	0.0054 (7)	0.0116 (6)
C16A	0.0192 (5)	0.0259 (5)	0.0167 (5)	−0.0003 (4)	−0.0003 (4)	0.0115 (4)
C17A	0.0230 (6)	0.0553 (9)	0.0363 (7)	0.0105 (5)	0.0073 (5)	0.0355 (7)
C18A	0.0446 (8)	0.0412 (8)	0.0298 (6)	0.0173 (6)	0.0119 (6)	0.0207 (6)
O1B	0.0247 (4)	0.0356 (5)	0.0264 (4)	−0.0053 (3)	−0.0075 (3)	0.0201 (4)
O2B	0.0325 (4)	0.0206 (4)	0.0231 (4)	0.0069 (3)	−0.0027 (3)	0.0103 (3)
N1B	0.0166 (4)	0.0256 (5)	0.0178 (4)	0.0042 (3)	−0.0004 (3)	0.0124 (4)
N2B	0.0162 (4)	0.0246 (5)	0.0176 (4)	0.0013 (3)	−0.0015 (3)	0.0124 (4)
C1B	0.0136 (4)	0.0387 (6)	0.0210 (5)	0.0017 (4)	0.0019 (4)	0.0197 (5)
C2B	0.0162 (5)	0.0473 (7)	0.0215 (5)	0.0029 (5)	−0.0004 (4)	0.0220 (5)
C3B	0.0276 (6)	0.0490 (8)	0.0256 (6)	0.0146 (5)	0.0020 (5)	0.0241 (6)
C4B	0.0372 (7)	0.0367 (7)	0.0278 (6)	0.0158 (6)	0.0020 (5)	0.0182 (5)
C5B	0.0261 (6)	0.0343 (6)	0.0202 (5)	0.0103 (5)	0.0016 (4)	0.0138 (5)
C6B	0.0134 (4)	0.0346 (6)	0.0180 (5)	0.0057 (4)	0.0027 (4)	0.0160 (4)
C7B	0.0144 (4)	0.0299 (6)	0.0172 (5)	0.0042 (4)	0.0014 (3)	0.0141 (4)
C8B	0.0150 (4)	0.0179 (5)	0.0161 (4)	−0.0010 (4)	−0.0012 (3)	0.0098 (4)
C9B	0.0134 (4)	0.0228 (5)	0.0168 (4)	0.0009 (4)	−0.0005 (3)	0.0113 (4)
C10B	0.0230 (5)	0.0244 (5)	0.0181 (5)	0.0027 (4)	−0.0012 (4)	0.0097 (4)
C11B	0.0328 (6)	0.0310 (6)	0.0184 (5)	0.0019 (5)	−0.0058 (4)	0.0076 (5)
C12B	0.0299 (6)	0.0427 (7)	0.0203 (5)	0.0069 (5)	−0.0065 (4)	0.0135 (5)
C13B	0.0263 (6)	0.0357 (7)	0.0234 (5)	0.0100 (5)	−0.0021 (4)	0.0160 (5)
C14B	0.0182 (5)	0.0239 (5)	0.0183 (5)	0.0035 (4)	0.0009 (4)	0.0112 (4)
C15B	0.0461 (8)	0.0438 (8)	0.0347 (7)	−0.0164 (6)	−0.0191 (6)	0.0262 (7)
C16B	0.0189 (5)	0.0542 (8)	0.0363 (7)	−0.0069 (5)	−0.0063 (5)	0.0354 (7)
C17B	0.0206 (5)	0.0295 (6)	0.0180 (5)	0.0055 (4)	0.0025 (4)	0.0135 (4)
C18B	0.0700 (11)	0.0272 (7)	0.0393 (8)	0.0196 (7)	−0.0090 (7)	0.0140 (6)

Geometric parameters (Å, º) top

O1A—C1A	1.3673 (14)	O1B—C1B	1.3619 (15)
O1A—C15A	1.4237 (16)	O1B—C15B	1.4366 (16)
O2A—C14A	1.3656 (15)	O2B—C14B	1.3670 (14)
O2A—C18A	1.4325 (15)	O2B—C18B	1.4255 (15)
N1A—C7A	1.2835 (14)	N1B—C7B	1.2877 (14)
N1A—N2A	1.3954 (12)	N1B—N2B	1.3938 (12)
N2A—C8A	1.2821 (14)	N2B—C8B	1.2837 (13)
C1A—C2A	1.3935 (15)	C1B—C2B	1.4004 (15)
C1A—C6A	1.4053 (15)	C1B—C6B	1.4086 (16)
C2A—C3A	1.3875 (18)	C2B—C3B	1.382 (2)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.3828 (19)	C3B—C4B	1.385 (2)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.3904 (16)	C4B—C5B	1.3926 (16)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.3906 (15)	C5B—C6B	1.3946 (18)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.4876 (14)	C6B—C7B	1.4935 (14)
C7A—C16A	1.5044 (14)	C7B—C16B	1.4977 (17)
C8A—C9A	1.4929 (15)	C8B—C9B	1.4917 (13)
C8A—C17A	1.5013 (16)	C8B—C17B	1.5018 (14)
C9A—C10A	1.3935 (17)	C9B—C10B	1.3907 (15)
C9A—C14A	1.4052 (16)	C9B—C14B	1.4052 (15)
C10A—C11A	1.3936 (17)	C10B—C11B	1.3924 (15)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.3858 (19)	C11B—C12B	1.3876 (18)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.388 (2)	C12B—C13B	1.3870 (18)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.3990 (16)	C13B—C14B	1.3948 (15)
C13A—H13A	0.9300	C13B—H13B	0.9300
C15A—H15A	0.9600	C15B—H15D	0.9600
C15A—H15B	0.9600	C15B—H15E	0.9600
C15A—H15C	0.9600	C15B—H15F	0.9600
C16A—H16A	0.9600	C16B—H16D	0.9600
C16A—H16B	0.9600	C16B—H16E	0.9600
C16A—H16C	0.9600	C16B—H16F	0.9600
C17A—H17A	0.9600	C17B—H17D	0.9600
C17A—H17B	0.9600	C17B—H17E	0.9600
C17A—H17C	0.9600	C17B—H17F	0.9600
C18A—H18A	0.9600	C18B—H18D	0.9600
C18A—H18B	0.9600	C18B—H18E	0.9600
C18A—H18C	0.9600	C18B—H18F	0.9600

C1A—O1A—C15A	117.43 (10)	C1B—O1B—C15B	116.31 (10)
C14A—O2A—C18A	116.57 (10)	C14B—O2B—C18B	117.64 (10)
C7A—N1A—N2A	116.67 (9)	C7B—N1B—N2B	116.99 (9)
C8A—N2A—N1A	116.75 (9)	C8B—N2B—N1B	117.11 (9)
O1A—C1A—C2A	124.13 (10)	O1B—C1B—C2B	123.31 (11)
O1A—C1A—C6A	115.45 (9)	O1B—C1B—C6B	116.88 (9)
C2A—C1A—C6A	120.40 (10)	C2B—C1B—C6B	119.79 (12)
C3A—C2A—C1A	119.57 (11)	C3B—C2B—C1B	120.34 (12)
C3A—C2A—H2AA	120.2	C3B—C2B—H2BA	119.8
C1A—C2A—H2AA	120.2	C1B—C2B—H2BA	119.8
C4A—C3A—C2A	120.79 (11)	C2B—C3B—C4B	120.68 (11)
C4A—C3A—H3AA	119.6	C2B—C3B—H3BA	119.7
C2A—C3A—H3AA	119.6	C4B—C3B—H3BA	119.7
C3A—C4A—C5A	119.47 (11)	C3B—C4B—C5B	119.11 (13)
C3A—C4A—H4AA	120.3	C3B—C4B—H4BA	120.4
C5A—C4A—H4AA	120.3	C5B—C4B—H4BA	120.4
C4A—C5A—C6A	121.10 (11)	C4B—C5B—C6B	121.66 (12)
C4A—C5A—H5AA	119.4	C4B—C5B—H5BA	119.2
C6A—C5A—H5AA	119.4	C6B—C5B—H5BA	119.2
C5A—C6A—C1A	118.64 (10)	C5B—C6B—C1B	118.39 (10)
C5A—C6A—C7A	119.18 (10)	C5B—C6B—C7B	118.06 (10)
C1A—C6A—C7A	122.16 (9)	C1B—C6B—C7B	123.53 (11)
N1A—C7A—C6A	115.93 (9)	N1B—C7B—C6B	114.65 (10)
N1A—C7A—C16A	123.32 (9)	N1B—C7B—C16B	123.60 (9)
C6A—C7A—C16A	120.57 (9)	C6B—C7B—C16B	121.53 (9)
N2A—C8A—C9A	115.31 (10)	N2B—C8B—C9B	115.69 (9)
N2A—C8A—C17A	123.59 (10)	N2B—C8B—C17B	124.37 (9)
C9A—C8A—C17A	120.83 (9)	C9B—C8B—C17B	119.59 (9)
C10A—C9A—C14A	118.35 (10)	C10B—C9B—C14B	118.76 (9)
C10A—C9A—C8A	118.65 (10)	C10B—C9B—C8B	118.58 (9)
C14A—C9A—C8A	123.00 (11)	C14B—C9B—C8B	122.64 (10)
C9A—C10A—C11A	121.69 (12)	C9B—C10B—C11B	121.21 (11)
C9A—C10A—H10A	119.2	C9B—C10B—H10B	119.4
C11A—C10A—H10A	119.2	C11B—C10B—H10B	119.4
C12A—C11A—C10A	119.09 (13)	C12B—C11B—C10B	119.19 (11)
C12A—C11A—H11A	120.5	C12B—C11B—H11B	120.4
C10A—C11A—H11A	120.5	C10B—C11B—H11B	120.4
C11A—C12A—C13A	120.65 (11)	C13B—C12B—C11B	120.86 (11)
C11A—C12A—H12A	119.7	C13B—C12B—H12B	119.6
C13A—C12A—H12A	119.7	C11B—C12B—H12B	119.6
C12A—C13A—C14A	120.00 (11)	C12B—C13B—C14B	119.64 (11)
C12A—C13A—H13A	120.0	C12B—C13B—H13B	120.2
C14A—C13A—H13A	120.0	C14B—C13B—H13B	120.2
O2A—C14A—C13A	123.34 (11)	O2B—C14B—C13B	123.88 (10)
O2A—C14A—C9A	116.44 (10)	O2B—C14B—C9B	115.77 (9)
C13A—C14A—C9A	120.19 (12)	C13B—C14B—C9B	120.31 (11)
O1A—C15A—H15A	109.5	O1B—C15B—H15D	109.5
O1A—C15A—H15B	109.5	O1B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
O1A—C15A—H15C	109.5	O1B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
C7A—C16A—H16A	109.5	C7B—C16B—H16D	109.5
C7A—C16A—H16B	109.5	C7B—C16B—H16E	109.5
H16A—C16A—H16B	109.5	H16D—C16B—H16E	109.5
C7A—C16A—H16C	109.5	C7B—C16B—H16F	109.5
H16A—C16A—H16C	109.5	H16D—C16B—H16F	109.5
H16B—C16A—H16C	109.5	H16E—C16B—H16F	109.5
C8A—C17A—H17A	109.5	C8B—C17B—H17D	109.5
C8A—C17A—H17B	109.5	C8B—C17B—H17E	109.5
H17A—C17A—H17B	109.5	H17D—C17B—H17E	109.5
C8A—C17A—H17C	109.5	C8B—C17B—H17F	109.5
H17A—C17A—H17C	109.5	H17D—C17B—H17F	109.5
H17B—C17A—H17C	109.5	H17E—C17B—H17F	109.5
O2A—C18A—H18A	109.5	O2B—C18B—H18D	109.5
O2A—C18A—H18B	109.5	O2B—C18B—H18E	109.5
H18A—C18A—H18B	109.5	H18D—C18B—H18E	109.5
O2A—C18A—H18C	109.5	O2B—C18B—H18F	109.5
H18A—C18A—H18C	109.5	H18D—C18B—H18F	109.5
H18B—C18A—H18C	109.5	H18E—C18B—H18F	109.5

C7A—N1A—N2A—C8A	117.39 (11)	C7B—N1B—N2B—C8B	−121.46 (11)
C15A—O1A—C1A—C2A	−3.00 (17)	C15B—O1B—C1B—C2B	0.99 (16)
C15A—O1A—C1A—C6A	178.73 (12)	C15B—O1B—C1B—C6B	179.48 (11)
O1A—C1A—C2A—C3A	−179.01 (11)	O1B—C1B—C2B—C3B	177.84 (11)
C6A—C1A—C2A—C3A	−0.82 (17)	C6B—C1B—C2B—C3B	−0.61 (16)
C1A—C2A—C3A—C4A	0.69 (19)	C1B—C2B—C3B—C4B	−0.64 (18)
C2A—C3A—C4A—C5A	0.6 (2)	C2B—C3B—C4B—C5B	0.9 (2)
C3A—C4A—C5A—C6A	−1.75 (19)	C3B—C4B—C5B—C6B	0.11 (19)
C4A—C5A—C6A—C1A	1.61 (16)	C4B—C5B—C6B—C1B	−1.33 (17)
C4A—C5A—C6A—C7A	−177.40 (10)	C4B—C5B—C6B—C7B	177.19 (11)
O1A—C1A—C6A—C5A	178.03 (9)	O1B—C1B—C6B—C5B	−176.99 (10)
C2A—C1A—C6A—C5A	−0.31 (15)	C2B—C1B—C6B—C5B	1.56 (16)
O1A—C1A—C6A—C7A	−2.99 (14)	O1B—C1B—C6B—C7B	4.58 (15)
C2A—C1A—C6A—C7A	178.67 (10)	C2B—C1B—C6B—C7B	−176.86 (10)
N2A—N1A—C7A—C6A	169.23 (9)	N2B—N1B—C7B—C6B	−166.13 (9)
N2A—N1A—C7A—C16A	−5.92 (15)	N2B—N1B—C7B—C16B	8.60 (16)
C5A—C6A—C7A—N1A	−45.02 (14)	C5B—C6B—C7B—N1B	40.45 (14)
C1A—C6A—C7A—N1A	136.01 (11)	C1B—C6B—C7B—N1B	−141.12 (11)
C5A—C6A—C7A—C16A	130.28 (11)	C5B—C6B—C7B—C16B	−134.40 (12)
C1A—C6A—C7A—C16A	−48.69 (14)	C1B—C6B—C7B—C16B	44.04 (16)
N1A—N2A—C8A—C9A	167.25 (9)	N1B—N2B—C8B—C9B	−166.24 (9)
N1A—N2A—C8A—C17A	−6.81 (17)	N1B—N2B—C8B—C17B	6.97 (16)
N2A—C8A—C9A—C10A	−43.91 (14)	N2B—C8B—C9B—C10B	48.84 (14)
C17A—C8A—C9A—C10A	130.33 (12)	C17B—C8B—C9B—C10B	−124.72 (11)
N2A—C8A—C9A—C14A	136.44 (11)	N2B—C8B—C9B—C14B	−132.77 (11)
C17A—C8A—C9A—C14A	−49.33 (16)	C17B—C8B—C9B—C14B	53.67 (15)
C14A—C9A—C10A—C11A	1.51 (16)	C14B—C9B—C10B—C11B	−1.41 (17)
C8A—C9A—C10A—C11A	−178.16 (10)	C8B—C9B—C10B—C11B	177.04 (11)
C9A—C10A—C11A—C12A	0.19 (18)	C9B—C10B—C11B—C12B	1.50 (19)
C10A—C11A—C12A—C13A	−1.31 (18)	C10B—C11B—C12B—C13B	−0.5 (2)
C11A—C12A—C13A—C14A	0.68 (18)	C11B—C12B—C13B—C14B	−0.6 (2)
C18A—O2A—C14A—C13A	1.85 (15)	C18B—O2B—C14B—C13B	−1.54 (18)
C18A—O2A—C14A—C9A	−176.08 (10)	C18B—O2B—C14B—C9B	176.41 (12)
C12A—C13A—C14A—O2A	−176.79 (10)	C12B—C13B—C14B—O2B	178.53 (12)
C12A—C13A—C14A—C9A	1.07 (16)	C12B—C13B—C14B—C9B	0.67 (18)
C10A—C9A—C14A—O2A	175.87 (9)	C10B—C9B—C14B—O2B	−177.71 (10)
C8A—C9A—C14A—O2A	−4.47 (15)	C8B—C9B—C14B—O2B	3.90 (15)
C10A—C9A—C14A—C13A	−2.13 (15)	C10B—C9B—C14B—C13B	0.32 (16)
C8A—C9A—C14A—C13A	177.52 (10)	C8B—C9B—C14B—C13B	−178.07 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17B—H17F···O2B	0.96	2.36	2.9918 (17)	123
C15B—H15E···Cg1ⁱ	0.96	2.83	3.5974 (17)	138
C18A—H18C···Cg2ⁱⁱ	0.96	2.90	3.6976 (17)	141

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀N₂O₂
M_r	296.36
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.9695 (2), 14.8028 (4), 15.4704 (4)
α, β, γ (°)	117.909 (1), 90.151 (1), 91.979 (1)
V (Å³)	1611.46 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.55 × 0.37 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.957, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	39016, 9367, 7773
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.123, 1.02
No. of reflections	9367
No. of parameters	405
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.24

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17B—H17F···O2B	0.96	2.36	2.9918 (17)	123
C15B—H15E···Cg1ⁱ	0.96	2.83	3.5974 (17)	138
C18A—H18C···Cg2ⁱⁱ	0.96	2.90	3.6976 (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.

‡Thomson Reuters ResearcherID: A-5085-2009.

§Additional correspondence author, e-mail: hkfun@usm.my. Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

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.

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