(E)-2-(2,3-Dimethyl­anilino)-N′-[2-methyl-5-(prop-1-en-2-yl)cyclo­hex-2-enyl­idene]benzohydrazide

Bhat, M.A.; Abdel-Aziz, H.A.; Ghabbour, H.A.; Hemamalini, M.; Fun, H.-K.

doi:10.1107/S1600536812009087

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1135

doi:10.1107/S1600536812009087

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(E)-2-(2,3-Dimethylanilino)-N′-[2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enylidene]benzohydrazide

Mashooq A. Bhat,^a Hatem A. Abdel-Aziz,^a Hazem A. Ghabbour,^a Madhukar Hemamalini ^b and Hoong-Kun Fun ^b ^*‡

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 20 February 2012; accepted 29 February 2012; online 21 March 2012)

The asymmetric unit of the title compound, C₂₅H₂₉N₃O, comprises two crystallographically independent molecules. The dihedral angles between the benzene rings in the two molecules are 59.7 (2) and 61.27 (18)°. The cyclohexene rings adopt sofa and half-chair conformations. In the crystal, molecules are connected via N—H⋯O and weak C—H⋯O hydrogen bonds, forming chains along the a axis. In each molecule, there is an intramolecular N—H⋯O hydrogen bond.

Related literature

For background to the chemistry and biological activity of diaryl amines, see: Reddy et al. (2010 ); Ohta et al. (2008); Li et al. (2008). For related structures, see: Wang et al. (2010 ); Tian et al. (2010 ). For ring conformations, see: Cremer & Pople (1975 ). For standard bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₅H₂₉N₃O
M_r = 387.51
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.0296 (4) Å
b = 18.0457 (7) Å
c = 27.4755 (10) Å
V = 4477.0 (3) Å³
Z = 8
Cu Kα radiation
μ = 0.55 mm⁻¹
T = 296 K
10.28 × 0.28 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.070, T_max = 0.955
17464 measured reflections
7599 independent reflections
5248 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.167
S = 1.03
7599 reflections
531 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.11 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H2AB⋯O1B	0.86	2.31	2.969 (4)	134
N3A—H3AC⋯O1A	0.86	2.14	2.697 (3)	122
N2B—H2BB⋯O1Aⁱ	0.86	2.36	2.986 (4)	130
C5A—H5AB⋯O1B	0.97	2.47	3.189 (4)	130
C9A—H9AA⋯O1B	0.93	2.43	3.282 (4)	152
C5B—H5BA⋯O1Aⁱ	0.97	2.46	3.248 (4)	138
C9B—H9BA⋯O1Aⁱ	0.93	2.50	3.352 (4)	153
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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: 10.1107/S1600536812009087/lh5424sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812009087/lh5424Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812009087/lh5424Isup3.cml

checkCIF report

Comment top

Diarylamines represent an important class of compounds due to their wide applications and special pharmacological activities (Ohta et al., 2008; Li et al., 2008; Reddy et al., 2010). The crystal structues of 4-(o-Tolylamino) benzaldehyde (Wang et al., 2010) and 4-(p-Tolylamino) benzaldehyde (Tian et al., 2010) have been reported in the literature. Herein, we reported the crystal structure of the title compound, (I).

The asymmetric unit of the title compound consists of two crystallographically independent (E)-2-(2,3-dimethylphenylamino)- N'-(2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enylidene)benzohydrazide (A & B), as shown in Fig. 1. The bond lengths and angles of molecules A and B agree with each other and are within normal ranges for bond lengths (Allen et al., 1987). The dihedral angles between benzene rings (C8A–C13A)/(C15A–C20A), and (C8B–C13B)/(C15B–C20B) are 59.7 (2)° and 61.27 (18)° ° respectively. In molecule A (C1A–C6A), the cylcohexene rings adopts a sofa conformation [Q = 0.499 (4) Å, θ = 57.1 (5)°, φ = 176.4 (5)°]. In molecule B (C1B–C6B), the cyclohexene ring adopts a half-chair conformation [Q = 0.431 (4) Å, θ = 53.8 (5)°, φ = 195.3 (7)°; Cremer & Pople, 1975].

In the crystal structure (Fig. 2), molecules are connected via intermolecular N—H···O and C—H···O hydrogen bonds, forming one-dimensional chains along the a-axis. In each molecule the is an intramolecular N—H···O hydrogen bond.

Related literature top

For background to the chemistry and biological activity of diaryl amines, see: Reddy et al. (2010); Ohta et al. (2008); Li et al. (2008). For related structures, see: Wang et al. (2010); Tian et al. (2010). For ring conformations, see: Cremer & Pople (1975). For standard bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared by the reaction of carvone, 2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone (0.15 g, 1 mmol) and 2-(2,3-dimethylphenylamino)benzohydrazide (0.26 g, 1 mmol) in ETOH (25 mL). After stirring for 3 h, at room temperature, the resulting mixture was concentrated. The precipitate washed with ETOH to afford the title compound. Colorless blocks of the title compound suitable for X-ray structure determination were recrystallized from ETOH by the slow evaporation of the solvent at room temperature. The crystals are very brittle and shatter easily upon cutting so data were collected using a crystal which was a long needle.

Structure description top

For background to the chemistry and biological activity of diaryl amines, see: Reddy et al. (2010); Ohta et al. (2008); Li et al. (2008). For related structures, see: Wang et al. (2010); Tian et al. (2010). For ring conformations, see: Cremer & Pople (1975). For standard bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 asymmetric unit of the title compound, showing 10% probability displacement ellipsoids. Hydrogen atoms omitted for clarity.
	Fig. 2. The crystal packing of the title compound (I).

(E)-2-(2,3-Dimethylanilino)-N'-[2-methyl-5-(prop-1-en- 2-yl)cyclohex-2-enylidene]benzohydrazide top

Crystal data top

C₂₅H₂₉N₃O	F(000) = 1664
M_r = 387.51	D_x = 1.150 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6172 reflections
a = 9.0296 (4) Å	θ = 2.5–65.3°
b = 18.0457 (7) Å	µ = 0.55 mm⁻¹
c = 27.4755 (10) Å	T = 296 K
V = 4477.0 (3) Å³	Plate, colourless
Z = 8	10.28 × 0.28 × 0.09 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7599 independent reflections
Radiation source: fine-focus sealed tube	5248 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
φ and ω scans	θ_max = 69.7°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→10
T_min = 0.070, T_max = 0.955	k = −12→21
17464 measured reflections	l = −33→27

Refinement top

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)] = 0.059	H-atom parameters constrained
wR(F²) = 0.167	w = 1/[σ²(F_o²) + (0.0785P)² + 0.183P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
7599 reflections	Δρ_max = 0.13 e Å⁻³
531 parameters	Δρ_min = −0.11 e Å⁻³
0 restraints	Absolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876–881.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.4 (4)

Crystal data top

C₂₅H₂₉N₃O	V = 4477.0 (3) Å³
M_r = 387.51	Z = 8
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 9.0296 (4) Å	µ = 0.55 mm⁻¹
b = 18.0457 (7) Å	T = 296 K
c = 27.4755 (10) Å	10.28 × 0.28 × 0.09 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7599 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5248 reflections with I > 2σ(I)
T_min = 0.070, T_max = 0.955	R_int = 0.027
17464 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	H-atom parameters constrained
wR(F²) = 0.167	Δρ_max = 0.13 e Å⁻³
S = 1.03	Δρ_min = −0.11 e Å⁻³
7599 reflections	Absolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876–881.
531 parameters	Absolute structure parameter: 0.4 (4)
0 restraints

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.2413 (3)	0.94820 (14)	0.28577 (7)	0.0736 (7)
N1A	0.3747 (3)	0.88060 (15)	0.21179 (8)	0.0664 (7)
N2A	0.4546 (3)	0.91235 (16)	0.24990 (8)	0.0675 (7)
H2AB	0.5495	0.9087	0.2514	0.081*
N3A	0.2794 (4)	0.9594 (2)	0.38283 (10)	0.1008 (12)
H3AC	0.2101	0.9666	0.3619	0.121*
C1A	0.3585 (4)	0.8031 (2)	0.14399 (11)	0.0736 (10)
C2A	0.4237 (5)	0.7575 (2)	0.11367 (12)	0.0910 (13)
H2AA	0.3697	0.7423	0.0866	0.109*
C3A	0.5779 (5)	0.7279 (2)	0.11888 (13)	0.0961 (13)
H3AA	0.6469	0.7598	0.1018	0.115*
H3AB	0.5837	0.6788	0.1046	0.115*
C4A	0.6196 (4)	0.72406 (18)	0.17249 (12)	0.0730 (9)
H4AA	0.5503	0.6900	0.1884	0.088*
C5A	0.5956 (4)	0.80113 (18)	0.19480 (12)	0.0781 (10)
H5AA	0.6133	0.7985	0.2296	0.094*
H5AB	0.6672	0.8353	0.1810	0.094*
C6A	0.4416 (4)	0.83090 (18)	0.18604 (10)	0.0650 (9)
C7A	0.3777 (4)	0.94886 (17)	0.28411 (10)	0.0619 (8)
C8A	0.4679 (4)	0.9879 (2)	0.32151 (12)	0.0722 (10)
C9A	0.5983 (4)	1.0215 (2)	0.31003 (14)	0.0842 (11)
H9AA	0.6308	1.0214	0.2779	0.101*
C10A	0.6841 (6)	1.0562 (2)	0.34572 (18)	0.1142 (16)
H10A	0.7715	1.0803	0.3374	0.137*
C11A	0.6381 (6)	1.0544 (3)	0.39265 (18)	0.122 (2)
H11A	0.6965	1.0761	0.4166	0.146*
C12A	0.5076 (6)	1.0213 (3)	0.40553 (15)	0.1101 (17)
H12A	0.4788	1.0212	0.4380	0.132*
C13A	0.4167 (5)	0.9875 (2)	0.37067 (12)	0.0828 (12)
C15A	0.2381 (5)	0.9205 (2)	0.42506 (12)	0.0924 (14)
C16A	0.3442 (6)	0.8805 (3)	0.45099 (14)	0.1184 (19)
H16A	0.4438	0.8824	0.4425	0.142*
C17A	0.2956 (8)	0.8376 (3)	0.49022 (17)	0.130 (2)
H17A	0.3639	0.8098	0.5078	0.155*
C18A	0.1500 (9)	0.8358 (3)	0.50314 (17)	0.133 (2)
H18A	0.1205	0.8068	0.5294	0.160*
C19A	0.0454 (8)	0.8764 (3)	0.47784 (15)	0.1158 (18)
C20A	0.0899 (5)	0.9205 (2)	0.43834 (13)	0.0904 (12)
C21A	0.2037 (5)	0.8302 (2)	0.13614 (13)	0.1015 (14)
H21A	0.1631	0.8072	0.1076	0.152*
H21B	0.2045	0.8830	0.1319	0.152*
H21C	0.1440	0.8177	0.1639	0.152*
C22A	0.7733 (5)	0.6955 (2)	0.18154 (16)	0.0936 (13)
C23A	0.7884 (6)	0.6531 (3)	0.2257 (2)	0.180 (3)
H23A	0.8896	0.6379	0.2296	0.270*
H23B	0.7261	0.6100	0.2240	0.270*
H23C	0.7595	0.6830	0.2530	0.270*
C24A	0.8842 (7)	0.7103 (5)	0.1526 (2)	0.229 (4)
H24A	0.9899	0.6860	0.1562	0.275*
H24B	0.8867	0.7160	0.1200	0.275*
C25A	−0.1157 (7)	0.8735 (3)	0.49329 (17)	0.159 (3)
H25A	−0.1247	0.8442	0.5223	0.238*
H25B	−0.1737	0.8516	0.4678	0.238*
H25C	−0.1507	0.9228	0.4995	0.238*
C26A	−0.0165 (5)	0.9662 (3)	0.41017 (14)	0.1073 (15)
H26A	0.0245	1.0146	0.4050	0.161*
H26B	−0.1076	0.9704	0.4280	0.161*
H26C	−0.0353	0.9431	0.3793	0.161*
O1B	0.7412 (3)	0.96096 (13)	0.20763 (7)	0.0724 (6)
N1B	0.8694 (3)	0.88310 (15)	0.27897 (9)	0.0698 (7)
N2B	0.9491 (3)	0.91252 (16)	0.24059 (8)	0.0678 (7)
H2BB	1.0424	0.9041	0.2378	0.081*
N3B	0.7821 (3)	0.96889 (18)	0.10927 (9)	0.0841 (9)
H3BC	0.7106	0.9812	0.1283	0.101*
C1B	0.8460 (4)	0.7998 (2)	0.34366 (11)	0.0713 (9)
C2B	0.9011 (5)	0.7448 (2)	0.36978 (13)	0.0903 (12)
H2BA	0.8418	0.7261	0.3946	0.108*
C3B	1.0496 (5)	0.7098 (2)	0.36318 (14)	0.0930 (13)
H3BA	1.0375	0.6621	0.3473	0.112*
H3BB	1.0937	0.7011	0.3949	0.112*
C4B	1.1538 (4)	0.75777 (19)	0.33295 (12)	0.0740 (9)
H4BA	1.1827	0.7998	0.3534	0.089*
C5B	1.0720 (4)	0.78947 (19)	0.28944 (11)	0.0724 (9)
H5BA	1.1368	0.8239	0.2727	0.087*
H5BB	1.0493	0.7495	0.2671	0.087*
C6B	0.9309 (4)	0.82876 (19)	0.30236 (11)	0.0670 (9)
C7B	0.8768 (4)	0.95481 (18)	0.20755 (10)	0.0640 (8)
C8B	0.9715 (4)	0.99015 (18)	0.16985 (11)	0.0639 (8)
C9B	1.1097 (4)	1.01853 (19)	0.18149 (13)	0.0792 (10)
H9BA	1.1428	1.0162	0.2135	0.095*
C10B	1.1990 (5)	1.0501 (2)	0.14666 (15)	0.0911 (12)
H10B	1.2905	1.0701	0.1550	0.109*
C11B	1.1505 (5)	1.0517 (2)	0.09901 (15)	0.0945 (13)
H11B	1.2109	1.0718	0.0750	0.113*
C12B	1.0164 (5)	1.0243 (2)	0.08696 (13)	0.0856 (12)
H12B	0.9860	1.0259	0.0546	0.103*
C13B	0.9222 (5)	0.9935 (2)	0.12170 (11)	0.0733 (10)
C15B	0.7459 (4)	0.9258 (2)	0.06847 (10)	0.0733 (10)
C16B	0.8528 (5)	0.8825 (2)	0.04525 (11)	0.0933 (14)
H16B	0.9509	0.8842	0.0554	0.112*
C17B	0.8119 (6)	0.8375 (3)	0.00722 (13)	0.1074 (16)
H17B	0.8826	0.8081	−0.0081	0.129*
C18B	0.6666 (7)	0.8355 (3)	−0.00828 (14)	0.1052 (16)
H18B	0.6409	0.8048	−0.0341	0.126*
C19B	0.5590 (6)	0.8780 (2)	0.01349 (12)	0.0891 (12)
C20B	0.5990 (5)	0.9243 (2)	0.05283 (11)	0.0782 (10)
C21B	0.6965 (4)	0.8320 (2)	0.35377 (13)	0.0942 (12)
H21D	0.6567	0.8102	0.3829	0.141*
H21E	0.6316	0.8218	0.3269	0.141*
H21F	0.7051	0.8846	0.3580	0.141*
C22B	1.2935 (5)	0.7160 (2)	0.32092 (16)	0.0924 (12)
C23B	1.3893 (7)	0.6953 (4)	0.3598 (2)	0.194 (3)
H23D	1.4841	0.6813	0.3470	0.291*
H23E	1.3471	0.6542	0.3772	0.291*
H23F	1.4013	0.7365	0.3816	0.291*
C24B	1.3230 (7)	0.6901 (4)	0.27603 (19)	0.191 (3)
H24C	1.2857	0.7072	0.2426	0.229*
H24D	1.4223	0.6670	0.2761	0.229*
C25B	0.4013 (6)	0.8752 (3)	−0.00426 (16)	0.125 (2)
H25D	0.3961	0.8458	−0.0333	0.187*
H25G	0.3675	0.9246	−0.0111	0.187*
H25E	0.3396	0.8535	0.0204	0.187*
C26B	0.4872 (4)	0.9721 (2)	0.07800 (14)	0.0997 (13)
H26D	0.5257	1.0215	0.0812	0.150*
H26E	0.4666	0.9522	0.1097	0.150*
H26F	0.3976	0.9734	0.0592	0.150*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0700 (18)	0.0877 (18)	0.0632 (12)	0.0027 (13)	−0.0034 (11)	−0.0075 (11)
N1A	0.0782 (19)	0.0627 (17)	0.0584 (13)	−0.0030 (15)	−0.0032 (13)	−0.0049 (13)
N2A	0.0708 (19)	0.0670 (19)	0.0649 (14)	−0.0004 (14)	−0.0046 (12)	−0.0146 (13)
N3A	0.098 (3)	0.145 (3)	0.0598 (16)	0.015 (3)	−0.0047 (16)	−0.0036 (19)
C1A	0.092 (3)	0.067 (2)	0.0613 (17)	0.001 (2)	−0.0129 (17)	−0.0092 (16)
C2A	0.118 (4)	0.087 (3)	0.068 (2)	0.006 (3)	−0.025 (2)	−0.0193 (19)
C3A	0.123 (4)	0.084 (3)	0.081 (2)	0.011 (3)	−0.007 (2)	−0.022 (2)
C4A	0.086 (3)	0.0542 (19)	0.0786 (19)	−0.0020 (17)	−0.0021 (18)	−0.0001 (16)
C5A	0.095 (3)	0.059 (2)	0.080 (2)	0.0024 (19)	−0.0089 (19)	−0.0181 (16)
C6A	0.078 (2)	0.059 (2)	0.0576 (16)	−0.0044 (17)	−0.0033 (15)	−0.0015 (15)
C7A	0.070 (2)	0.0554 (19)	0.0604 (16)	0.0051 (16)	−0.0064 (15)	−0.0033 (14)
C8A	0.072 (2)	0.068 (2)	0.077 (2)	0.0162 (18)	−0.0140 (17)	−0.0227 (17)
C9A	0.074 (3)	0.075 (2)	0.104 (3)	0.009 (2)	−0.009 (2)	−0.028 (2)
C10A	0.100 (3)	0.091 (3)	0.152 (4)	0.001 (3)	−0.028 (3)	−0.052 (3)
C11A	0.116 (4)	0.125 (4)	0.124 (4)	0.025 (4)	−0.038 (3)	−0.071 (3)
C12A	0.121 (4)	0.124 (4)	0.085 (3)	0.033 (3)	−0.022 (3)	−0.036 (3)
C13A	0.086 (3)	0.091 (3)	0.072 (2)	0.022 (2)	−0.0162 (19)	−0.0193 (19)
C15A	0.138 (4)	0.083 (3)	0.0559 (18)	0.024 (3)	−0.020 (2)	−0.0173 (18)
C16A	0.171 (5)	0.115 (4)	0.069 (2)	0.042 (4)	−0.015 (3)	−0.022 (2)
C17A	0.199 (7)	0.113 (4)	0.077 (3)	0.034 (5)	−0.020 (4)	−0.012 (3)
C18A	0.228 (8)	0.104 (4)	0.067 (3)	0.003 (5)	−0.018 (4)	0.001 (3)
C19A	0.172 (6)	0.107 (4)	0.069 (2)	−0.025 (4)	−0.004 (3)	−0.021 (3)
C20A	0.115 (4)	0.088 (3)	0.068 (2)	−0.001 (3)	−0.002 (2)	−0.024 (2)
C21A	0.109 (4)	0.109 (3)	0.087 (3)	0.006 (3)	−0.021 (2)	−0.023 (2)
C22A	0.109 (4)	0.067 (3)	0.106 (3)	0.002 (2)	−0.011 (3)	−0.017 (2)
C23A	0.143 (5)	0.121 (5)	0.276 (8)	−0.016 (4)	−0.075 (5)	0.085 (5)
C24A	0.099 (5)	0.421 (13)	0.167 (6)	0.082 (7)	0.018 (4)	0.068 (8)
C25A	0.197 (7)	0.182 (6)	0.098 (3)	−0.065 (6)	0.015 (4)	−0.008 (4)
C26A	0.108 (4)	0.117 (4)	0.097 (3)	0.008 (3)	−0.007 (2)	−0.013 (3)
O1B	0.0701 (18)	0.0785 (16)	0.0686 (12)	−0.0017 (13)	0.0039 (11)	0.0031 (11)
N1B	0.082 (2)	0.0648 (18)	0.0626 (14)	−0.0070 (16)	0.0047 (13)	0.0073 (13)
N2B	0.073 (2)	0.0683 (19)	0.0623 (14)	0.0008 (15)	0.0036 (13)	0.0092 (13)
N3B	0.081 (2)	0.108 (3)	0.0635 (15)	0.0155 (19)	0.0035 (14)	−0.0139 (16)
C1B	0.080 (2)	0.067 (2)	0.0670 (18)	−0.0037 (18)	0.0095 (16)	0.0067 (16)
C2B	0.104 (3)	0.086 (3)	0.081 (2)	−0.004 (2)	0.027 (2)	0.010 (2)
C3B	0.102 (3)	0.089 (3)	0.088 (2)	0.009 (2)	0.022 (2)	0.024 (2)
C4B	0.086 (3)	0.062 (2)	0.0742 (19)	−0.0055 (18)	−0.0005 (17)	0.0027 (16)
C5B	0.077 (2)	0.071 (2)	0.0693 (18)	−0.0075 (18)	0.0107 (16)	0.0059 (16)
C6B	0.080 (2)	0.062 (2)	0.0588 (16)	−0.0084 (18)	0.0014 (16)	0.0013 (15)
C7B	0.076 (3)	0.055 (2)	0.0606 (16)	−0.0002 (17)	0.0009 (15)	−0.0043 (14)
C8B	0.072 (2)	0.0546 (19)	0.0650 (17)	0.0072 (15)	0.0078 (15)	0.0021 (15)
C9B	0.086 (3)	0.066 (2)	0.085 (2)	0.003 (2)	0.008 (2)	0.0115 (18)
C10B	0.077 (3)	0.079 (3)	0.117 (3)	−0.004 (2)	0.016 (2)	0.020 (2)
C11B	0.098 (3)	0.084 (3)	0.101 (3)	0.016 (3)	0.034 (2)	0.030 (2)
C12B	0.098 (3)	0.087 (3)	0.071 (2)	0.018 (2)	0.017 (2)	0.014 (2)
C13B	0.086 (3)	0.072 (2)	0.0616 (17)	0.015 (2)	0.0103 (17)	0.0042 (16)
C15B	0.087 (3)	0.082 (3)	0.0509 (15)	0.012 (2)	0.0037 (16)	0.0110 (16)
C16B	0.118 (4)	0.098 (3)	0.0641 (19)	0.034 (3)	0.005 (2)	0.003 (2)
C17B	0.154 (5)	0.098 (3)	0.071 (2)	0.019 (3)	0.020 (3)	−0.012 (2)
C18B	0.151 (5)	0.100 (3)	0.065 (2)	−0.017 (3)	0.013 (3)	−0.007 (2)
C19B	0.118 (4)	0.087 (3)	0.0628 (19)	−0.009 (3)	−0.001 (2)	0.0129 (19)
C20B	0.101 (3)	0.070 (2)	0.0643 (18)	0.004 (2)	0.0068 (19)	0.0105 (17)
C21B	0.091 (3)	0.098 (3)	0.094 (2)	0.005 (2)	0.031 (2)	0.015 (2)
C22B	0.094 (3)	0.077 (3)	0.106 (3)	0.006 (2)	0.011 (2)	0.017 (2)
C23B	0.138 (6)	0.254 (8)	0.190 (6)	0.068 (6)	−0.049 (5)	−0.025 (6)
C24B	0.199 (6)	0.262 (8)	0.113 (4)	0.137 (6)	0.021 (4)	0.001 (5)
C25B	0.138 (5)	0.130 (4)	0.107 (3)	−0.044 (4)	−0.024 (3)	0.017 (3)
C26B	0.088 (3)	0.101 (3)	0.110 (3)	0.002 (3)	0.004 (2)	0.001 (3)

Geometric parameters (Å, º) top

O1A—C7A	1.232 (4)	O1B—C7B	1.230 (4)
N1A—C6A	1.292 (4)	N1B—C6B	1.297 (4)
N1A—N2A	1.394 (3)	N1B—N2B	1.383 (3)
N2A—C7A	1.342 (4)	N2B—C7B	1.354 (4)
N2A—H2AB	0.8600	N2B—H2BB	0.8600
N3A—C13A	1.381 (5)	N3B—C13B	1.383 (5)
N3A—C15A	1.406 (5)	N3B—C15B	1.403 (4)
N3A—H3AC	0.8600	N3B—H3BC	0.8600
C1A—C2A	1.311 (5)	C1B—C2B	1.323 (5)
C1A—C6A	1.466 (4)	C1B—C6B	1.466 (4)
C1A—C21A	1.496 (5)	C1B—C21B	1.496 (5)
C2A—C3A	1.499 (6)	C2B—C3B	1.494 (5)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.522 (5)	C3B—C4B	1.525 (5)
C3A—H3AA	0.9700	C3B—H3BA	0.9700
C3A—H3AB	0.9700	C3B—H3BB	0.9700
C4A—C22A	1.501 (5)	C4B—C22B	1.506 (5)
C4A—C5A	1.535 (4)	C4B—C5B	1.517 (4)
C4A—H4AA	0.9800	C4B—H4BA	0.9800
C5A—C6A	1.510 (5)	C5B—C6B	1.501 (5)
C5A—H5AA	0.9700	C5B—H5BA	0.9700
C5A—H5AB	0.9700	C5B—H5BB	0.9700
C7A—C8A	1.489 (4)	C7B—C8B	1.487 (4)
C8A—C9A	1.361 (5)	C8B—C9B	1.387 (5)
C8A—C13A	1.428 (5)	C8B—C13B	1.397 (4)
C9A—C10A	1.398 (5)	C9B—C10B	1.375 (5)
C9A—H9AA	0.9300	C9B—H9BA	0.9300
C10A—C11A	1.355 (6)	C10B—C11B	1.381 (5)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.367 (7)	C11B—C12B	1.349 (5)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.401 (5)	C12B—C13B	1.394 (5)
C12A—H12A	0.9300	C12B—H12B	0.9300
C15A—C20A	1.387 (6)	C15B—C20B	1.394 (5)
C15A—C16A	1.395 (6)	C15B—C16B	1.396 (5)
C16A—C17A	1.398 (7)	C16B—C17B	1.374 (5)
C16A—H16A	0.9300	C16B—H16B	0.9300
C17A—C18A	1.362 (8)	C17B—C18B	1.380 (7)
C17A—H17A	0.9300	C17B—H17B	0.9300
C18A—C19A	1.384 (7)	C18B—C19B	1.374 (6)
C18A—H18A	0.9300	C18B—H18B	0.9300
C19A—C20A	1.404 (6)	C19B—C20B	1.414 (5)
C19A—C25A	1.516 (7)	C19B—C25B	1.506 (6)
C20A—C26A	1.484 (5)	C20B—C26B	1.497 (5)
C21A—H21A	0.9600	C21B—H21D	0.9600
C21A—H21B	0.9600	C21B—H21E	0.9600
C21A—H21C	0.9600	C21B—H21F	0.9600
C22A—C24A	1.305 (7)	C22B—C24B	1.346 (6)
C22A—C23A	1.443 (6)	C22B—C23B	1.425 (6)
C23A—H23A	0.9600	C23B—H23D	0.9600
C23A—H23B	0.9600	C23B—H23E	0.9600
C23A—H23C	0.9600	C23B—H23F	0.9600
C24A—H24A	1.0556	C24B—H24C	1.0268
C24A—H24B	0.9026	C24B—H24D	0.9881
C25A—H25A	0.9600	C25B—H25D	0.9600
C25A—H25B	0.9600	C25B—H25G	0.9600
C25A—H25C	0.9600	C25B—H25E	0.9600
C26A—H26A	0.9600	C26B—H26D	0.9600
C26A—H26B	0.9600	C26B—H26E	0.9600
C26A—H26C	0.9600	C26B—H26F	0.9600

C6A—N1A—N2A	117.1 (3)	C6B—N1B—N2B	116.4 (3)
C7A—N2A—N1A	117.4 (3)	C7B—N2B—N1B	118.5 (3)
C7A—N2A—H2AB	121.3	C7B—N2B—H2BB	120.8
N1A—N2A—H2AB	121.3	N1B—N2B—H2BB	120.8
C13A—N3A—C15A	128.4 (4)	C13B—N3B—C15B	126.0 (3)
C13A—N3A—H3AC	115.8	C13B—N3B—H3BC	117.0
C15A—N3A—H3AC	115.8	C15B—N3B—H3BC	117.0
C2A—C1A—C6A	119.1 (4)	C2B—C1B—C6B	119.4 (4)
C2A—C1A—C21A	122.2 (3)	C2B—C1B—C21B	122.0 (3)
C6A—C1A—C21A	118.7 (3)	C6B—C1B—C21B	118.5 (3)
C1A—C2A—C3A	125.5 (4)	C1B—C2B—C3B	126.1 (3)
C1A—C2A—H2AA	117.2	C1B—C2B—H2BA	116.9
C3A—C2A—H2AA	117.2	C3B—C2B—H2BA	116.9
C2A—C3A—C4A	109.8 (3)	C2B—C3B—C4B	112.3 (3)
C2A—C3A—H3AA	109.7	C2B—C3B—H3BA	109.1
C4A—C3A—H3AA	109.7	C4B—C3B—H3BA	109.1
C2A—C3A—H3AB	109.7	C2B—C3B—H3BB	109.1
C4A—C3A—H3AB	109.7	C4B—C3B—H3BB	109.1
H3AA—C3A—H3AB	108.2	H3BA—C3B—H3BB	107.9
C22A—C4A—C3A	113.8 (3)	C22B—C4B—C5B	115.1 (3)
C22A—C4A—C5A	112.0 (3)	C22B—C4B—C3B	110.6 (3)
C3A—C4A—C5A	108.1 (3)	C5B—C4B—C3B	110.1 (3)
C22A—C4A—H4AA	107.5	C22B—C4B—H4BA	106.9
C3A—C4A—H4AA	107.5	C5B—C4B—H4BA	106.9
C5A—C4A—H4AA	107.5	C3B—C4B—H4BA	106.9
C6A—C5A—C4A	112.9 (3)	C6B—C5B—C4B	113.9 (3)
C6A—C5A—H5AA	109.0	C6B—C5B—H5BA	108.8
C4A—C5A—H5AA	109.0	C4B—C5B—H5BA	108.8
C6A—C5A—H5AB	109.0	C6B—C5B—H5BB	108.8
C4A—C5A—H5AB	109.0	C4B—C5B—H5BB	108.8
H5AA—C5A—H5AB	107.8	H5BA—C5B—H5BB	107.7
N1A—C6A—C1A	115.5 (3)	N1B—C6B—C1B	115.4 (3)
N1A—C6A—C5A	126.1 (3)	N1B—C6B—C5B	127.1 (3)
C1A—C6A—C5A	118.4 (3)	C1B—C6B—C5B	117.3 (3)
O1A—C7A—N2A	122.6 (3)	O1B—C7B—N2B	122.0 (3)
O1A—C7A—C8A	121.7 (3)	O1B—C7B—C8B	122.4 (3)
N2A—C7A—C8A	115.7 (3)	N2B—C7B—C8B	115.6 (3)
C9A—C8A—C13A	120.1 (3)	C9B—C8B—C13B	119.3 (3)
C9A—C8A—C7A	121.6 (3)	C9B—C8B—C7B	121.0 (3)
C13A—C8A—C7A	118.3 (4)	C13B—C8B—C7B	119.7 (3)
C8A—C9A—C10A	121.1 (4)	C10B—C9B—C8B	121.4 (4)
C8A—C9A—H9AA	119.5	C10B—C9B—H9BA	119.3
C10A—C9A—H9AA	119.5	C8B—C9B—H9BA	119.3
C11A—C10A—C9A	119.1 (5)	C9B—C10B—C11B	118.9 (4)
C11A—C10A—H10A	120.4	C9B—C10B—H10B	120.6
C9A—C10A—H10A	120.4	C11B—C10B—H10B	120.6
C10A—C11A—C12A	121.4 (4)	C12B—C11B—C10B	120.6 (4)
C10A—C11A—H11A	119.3	C12B—C11B—H11B	119.7
C12A—C11A—H11A	119.3	C10B—C11B—H11B	119.7
C11A—C12A—C13A	121.2 (4)	C11B—C12B—C13B	121.7 (4)
C11A—C12A—H12A	119.4	C11B—C12B—H12B	119.1
C13A—C12A—H12A	119.4	C13B—C12B—H12B	119.1
N3A—C13A—C12A	121.4 (4)	N3B—C13B—C12B	121.1 (3)
N3A—C13A—C8A	121.5 (3)	N3B—C13B—C8B	120.7 (3)
C12A—C13A—C8A	117.0 (4)	C12B—C13B—C8B	118.1 (4)
C20A—C15A—C16A	121.9 (4)	C20B—C15B—C16B	120.4 (4)
C20A—C15A—N3A	118.2 (4)	C20B—C15B—N3B	118.6 (3)
C16A—C15A—N3A	119.8 (5)	C16B—C15B—N3B	120.9 (3)
C15A—C16A—C17A	117.7 (6)	C17B—C16B—C15B	119.5 (4)
C15A—C16A—H16A	121.2	C17B—C16B—H16B	120.2
C17A—C16A—H16A	121.2	C15B—C16B—H16B	120.2
C18A—C17A—C16A	121.1 (6)	C16B—C17B—C18B	120.3 (5)
C18A—C17A—H17A	119.4	C16B—C17B—H17B	119.8
C16A—C17A—H17A	119.4	C18B—C17B—H17B	119.8
C17A—C18A—C19A	121.0 (6)	C19B—C18B—C17B	121.6 (4)
C17A—C18A—H18A	119.5	C19B—C18B—H18B	119.2
C19A—C18A—H18A	119.5	C17B—C18B—H18B	119.2
C18A—C19A—C20A	119.5 (6)	C18B—C19B—C20B	118.8 (5)
C18A—C19A—C25A	119.8 (5)	C18B—C19B—C25B	120.6 (4)
C20A—C19A—C25A	120.7 (6)	C20B—C19B—C25B	120.6 (5)
C15A—C20A—C19A	118.7 (5)	C15B—C20B—C19B	119.3 (4)
C15A—C20A—C26A	119.2 (4)	C15B—C20B—C26B	119.2 (3)
C19A—C20A—C26A	122.2 (5)	C19B—C20B—C26B	121.5 (4)
C1A—C21A—H21A	109.5	C1B—C21B—H21D	109.5
C1A—C21A—H21B	109.5	C1B—C21B—H21E	109.5
H21A—C21A—H21B	109.5	H21D—C21B—H21E	109.5
C1A—C21A—H21C	109.5	C1B—C21B—H21F	109.5
H21A—C21A—H21C	109.5	H21D—C21B—H21F	109.5
H21B—C21A—H21C	109.5	H21E—C21B—H21F	109.5
C24A—C22A—C23A	123.3 (5)	C24B—C22B—C23B	118.5 (5)
C24A—C22A—C4A	122.6 (5)	C24B—C22B—C4B	122.7 (4)
C23A—C22A—C4A	114.1 (4)	C23B—C22B—C4B	118.3 (4)
C22A—C23A—H23A	109.5	C22B—C23B—H23D	109.5
C22A—C23A—H23B	109.5	C22B—C23B—H23E	109.5
H23A—C23A—H23B	109.5	H23D—C23B—H23E	109.5
C22A—C23A—H23C	109.5	C22B—C23B—H23F	109.5
H23A—C23A—H23C	109.5	H23D—C23B—H23F	109.5
H23B—C23A—H23C	109.5	H23E—C23B—H23F	109.5
C22A—C24A—H24A	123.5	C22B—C24B—H24C	130.6
C22A—C24A—H24B	130.3	C22B—C24B—H24D	108.9
H24A—C24A—H24B	96.7	H24C—C24B—H24D	115.2
C19A—C25A—H25A	109.5	C19B—C25B—H25D	109.5
C19A—C25A—H25B	109.5	C19B—C25B—H25G	109.5
H25A—C25A—H25B	109.5	H25D—C25B—H25G	109.5
C19A—C25A—H25C	109.5	C19B—C25B—H25E	109.5
H25A—C25A—H25C	109.5	H25D—C25B—H25E	109.5
H25B—C25A—H25C	109.5	H25G—C25B—H25E	109.5
C20A—C26A—H26A	109.5	C20B—C26B—H26D	109.5
C20A—C26A—H26B	109.5	C20B—C26B—H26E	109.5
H26A—C26A—H26B	109.5	H26D—C26B—H26E	109.5
C20A—C26A—H26C	109.5	C20B—C26B—H26F	109.5
H26A—C26A—H26C	109.5	H26D—C26B—H26F	109.5
H26B—C26A—H26C	109.5	H26E—C26B—H26F	109.5

C6A—N1A—N2A—C7A	−163.2 (3)	C6B—N1B—N2B—C7B	162.9 (3)
C6A—C1A—C2A—C3A	2.4 (6)	C6B—C1B—C2B—C3B	3.4 (6)
C21A—C1A—C2A—C3A	−179.9 (4)	C21B—C1B—C2B—C3B	−178.9 (4)
C1A—C2A—C3A—C4A	28.6 (6)	C1B—C2B—C3B—C4B	17.1 (6)
C2A—C3A—C4A—C22A	−179.5 (3)	C2B—C3B—C4B—C22B	−171.6 (4)
C2A—C3A—C4A—C5A	−54.3 (4)	C2B—C3B—C4B—C5B	−43.4 (5)
C22A—C4A—C5A—C6A	179.9 (3)	C22B—C4B—C5B—C6B	178.2 (3)
C3A—C4A—C5A—C6A	53.7 (4)	C3B—C4B—C5B—C6B	52.5 (4)
N2A—N1A—C6A—C1A	−175.3 (3)	N2B—N1B—C6B—C1B	178.5 (3)
N2A—N1A—C6A—C5A	3.2 (5)	N2B—N1B—C6B—C5B	−6.4 (5)
C2A—C1A—C6A—N1A	174.1 (3)	C2B—C1B—C6B—N1B	−179.5 (3)
C21A—C1A—C6A—N1A	−3.7 (5)	C21B—C1B—C6B—N1B	2.8 (5)
C2A—C1A—C6A—C5A	−4.6 (5)	C2B—C1B—C6B—C5B	4.9 (5)
C21A—C1A—C6A—C5A	177.7 (3)	C21B—C1B—C6B—C5B	−172.8 (3)
C4A—C5A—C6A—N1A	156.9 (3)	C4B—C5B—C6B—N1B	151.3 (3)
C4A—C5A—C6A—C1A	−24.7 (5)	C4B—C5B—C6B—C1B	−33.7 (4)
N1A—N2A—C7A—O1A	8.1 (5)	N1B—N2B—C7B—O1B	−8.2 (5)
N1A—N2A—C7A—C8A	−174.4 (3)	N1B—N2B—C7B—C8B	174.7 (3)
O1A—C7A—C8A—C9A	−146.1 (4)	O1B—C7B—C8B—C9B	144.2 (4)
N2A—C7A—C8A—C9A	36.4 (5)	N2B—C7B—C8B—C9B	−38.7 (5)
O1A—C7A—C8A—C13A	35.8 (5)	O1B—C7B—C8B—C13B	−37.3 (5)
N2A—C7A—C8A—C13A	−141.7 (3)	N2B—C7B—C8B—C13B	139.8 (3)
C13A—C8A—C9A—C10A	−0.2 (6)	C13B—C8B—C9B—C10B	0.3 (6)
C7A—C8A—C9A—C10A	−178.2 (3)	C7B—C8B—C9B—C10B	178.8 (3)
C8A—C9A—C10A—C11A	1.9 (7)	C8B—C9B—C10B—C11B	−1.6 (6)
C9A—C10A—C11A—C12A	−2.0 (8)	C9B—C10B—C11B—C12B	1.5 (6)
C10A—C11A—C12A—C13A	0.4 (8)	C10B—C11B—C12B—C13B	−0.1 (7)
C15A—N3A—C13A—C12A	−39.7 (7)	C15B—N3B—C13B—C12B	45.2 (6)
C15A—N3A—C13A—C8A	144.6 (4)	C15B—N3B—C13B—C8B	−136.8 (4)
C11A—C12A—C13A—N3A	−174.6 (4)	C11B—C12B—C13B—N3B	176.8 (4)
C11A—C12A—C13A—C8A	1.3 (7)	C11B—C12B—C13B—C8B	−1.3 (6)
C9A—C8A—C13A—N3A	174.5 (4)	C9B—C8B—C13B—N3B	−176.9 (3)
C7A—C8A—C13A—N3A	−7.4 (6)	C7B—C8B—C13B—N3B	4.5 (5)
C9A—C8A—C13A—C12A	−1.4 (6)	C9B—C8B—C13B—C12B	1.2 (5)
C7A—C8A—C13A—C12A	176.7 (4)	C7B—C8B—C13B—C12B	−177.4 (3)
C13A—N3A—C15A—C20A	157.1 (4)	C13B—N3B—C15B—C20B	−160.8 (3)
C13A—N3A—C15A—C16A	−25.8 (6)	C13B—N3B—C15B—C16B	22.1 (6)
C20A—C15A—C16A—C17A	2.4 (6)	C20B—C15B—C16B—C17B	−1.0 (6)
N3A—C15A—C16A—C17A	−174.6 (4)	N3B—C15B—C16B—C17B	176.1 (4)
C15A—C16A—C17A—C18A	−1.0 (8)	C15B—C16B—C17B—C18B	0.7 (7)
C16A—C17A—C18A—C19A	0.0 (9)	C16B—C17B—C18B—C19B	−0.1 (8)
C17A—C18A—C19A—C20A	−0.2 (8)	C17B—C18B—C19B—C20B	−0.2 (7)
C17A—C18A—C19A—C25A	−179.7 (6)	C17B—C18B—C19B—C25B	179.7 (4)
C16A—C15A—C20A—C19A	−2.7 (6)	C16B—C15B—C20B—C19B	0.7 (5)
N3A—C15A—C20A—C19A	174.4 (3)	N3B—C15B—C20B—C19B	−176.5 (3)
C16A—C15A—C20A—C26A	177.9 (4)	C16B—C15B—C20B—C26B	−179.1 (3)
N3A—C15A—C20A—C26A	−5.1 (6)	N3B—C15B—C20B—C26B	3.7 (5)
C18A—C19A—C20A—C15A	1.5 (6)	C18B—C19B—C20B—C15B	−0.1 (6)
C25A—C19A—C20A—C15A	−179.0 (4)	C25B—C19B—C20B—C15B	−180.0 (4)
C18A—C19A—C20A—C26A	−179.1 (4)	C18B—C19B—C20B—C26B	179.7 (4)
C25A—C19A—C20A—C26A	0.4 (7)	C25B—C19B—C20B—C26B	−0.2 (6)
C3A—C4A—C22A—C24A	35.6 (7)	C5B—C4B—C22B—C24B	−18.2 (7)
C5A—C4A—C22A—C24A	−87.4 (7)	C3B—C4B—C22B—C24B	107.3 (6)
C3A—C4A—C22A—C23A	−146.6 (4)	C5B—C4B—C22B—C23B	169.7 (5)
C5A—C4A—C22A—C23A	90.4 (5)	C3B—C4B—C22B—C23B	−64.9 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2AB···O1B	0.86	2.31	2.969 (4)	134
N3A—H3AC···O1A	0.86	2.14	2.697 (3)	122
N2B—H2BB···O1Aⁱ	0.86	2.36	2.986 (4)	130
C5A—H5AB···O1B	0.97	2.47	3.189 (4)	130
C9A—H9AA···O1B	0.93	2.43	3.282 (4)	152
C5B—H5BA···O1Aⁱ	0.97	2.46	3.248 (4)	138
C9B—H9BA···O1Aⁱ	0.93	2.50	3.352 (4)	153

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₉N₃O
M_r	387.51
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	9.0296 (4), 18.0457 (7), 27.4755 (10)
V (Å³)	4477.0 (3)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	0.55
Crystal size (mm)	10.28 × 0.28 × 0.09

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.070, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	17464, 7599, 5248
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.608

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.167, 1.03
No. of reflections	7599
No. of parameters	531
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.11
Absolute structure	Flack, H. D. (1983). Acta Cryst. A39, 876–881.
Absolute structure parameter	0.4 (4)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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
N2A—H2AB···O1B	0.8600	2.3100	2.969 (4)	134.00
N3A—H3AC···O1A	0.8600	2.1400	2.697 (3)	122.00
N2B—H2BB···O1Aⁱ	0.8600	2.3600	2.986 (4)	130.00
C5A—H5AB···O1B	0.9700	2.4700	3.189 (4)	130.00
C9A—H9AA···O1B	0.9300	2.4300	3.282 (4)	152.00
C5B—H5BA···O1Aⁱ	0.9700	2.4600	3.248 (4)	138.00
C9B—H9BA···O1Aⁱ	0.9300	2.5000	3.352 (4)	153.00

Symmetry code: (i) x+1, y, z.

Footnotes

‡College of Pharmacy (Visiting Professor), King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia. Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

MAB, HAA and HAG thank the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University. MH and HFK thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Li, S. L., Ai, X. P., Feng, J. K., Cao, Y. L. & Yang, H. X. (2008). J. Power Sources, 184, 553–556. Web of Science CrossRef CAS Google Scholar
Ohta, K., Chiba, Y., Ogawa, T. & Endo, Y. (2008). Bioorg. Med. Chem. Lett. 18, 5050–5053. Web of Science CrossRef PubMed CAS Google Scholar
Reddy, L. V., Suman, A., Beevi, S. S., Mangamoori, L. N., Mukkanti, K. & Pal, S. (2010). J. Braz. Chem. Soc. 21, 98–104. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tian, X., Xie, Y.-S. & Zuo, H. (2010). Acta Cryst. E66, o2828. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Volume 68| Part 4| April 2012| Page o1135

doi:10.1107/S1600536812009087

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(E)-2-(2,3-Di­methyl­anilino)-N′-[2-methyl-5-(prop-1-en-2-yl)cyclo­hex-2-enyl­­idene]benzohydrazide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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Acknowledgements

References

organic compounds

(E)-2-(2,3-Dimethylanilino)-N′-[2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enylidene]benzohydrazide