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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 4| April 2012| Page o926
doi:10.1107/S1600536812008367

(1Z,2E)-N′-{2-Chloro-1-methyl-2-[2-(4-methyl­phen­yl)hydrazin-1-yl­­idene]ethyl­­idene}-4-meth­­oxy­benzohydrazide

Hatem A. Abdel-Aziz,a Hazem A. Ghabbour,a Madhukar Hemamalinib and Hoong-Kun Funb*‡

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 23 February 2012; accepted 24 February 2012; online 3 March 2012)

The asymmetric unit of the title compound, C18H19ClN4O2, contains two mol­ecules, in which the dihedral angles between the benzene rings are 43.60 (12) and 58.65 (13)°. The hydrazine N atoms are twisted slightly out of the planes of the tolyl and meth­oxy­benzene rings: the C—C—N—N and N—N—C—C torsion angles are 171.1 (2) and −174.4 (2)°, respectively, for one mol­ecule and −177.4 (2) and −170.6 (2)°, respectively, for the other. In the crystal, mol­ecules are linked by N—H⋯O and C—H⋯O hydrogen bonds into chains propagating along the b-axis direction.

Related literature

For related structures and background to the bioactivity of hydrazones, see: Chantrapromma et al. (2011[Chantrapromma, S., Nilwanna, B., Jansrisewangwong, P., Kobkeatthawin, T. & Fun, H.-K. (2011). Acta Cryst. E67, o3499-o3500.]); Fun et al. (2012[Fun, H.-K., Nilwanna, B., Chantrapromma, S. & Razak, I. A. (2012). Acta Cryst. E68, o398-o399.]); Abdel-Aziz & Mekawey (2009[Abdel-Aziz, H. A. & Mekawey, A. A. I. (2009). Eur. J. Med. Chem. 44, 3985-4997.]); Abdel-Aziz et al. (2010[Abdel-Aziz, H. A., Abdel-Wahab, B. F. & Badria, F. A. (2010). Arch. Pharm. 343, 152-159.]). For reference bond lengths, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data

  • C18H19ClN4O2

  • Mr = 358.82

  • Monoclinic, P 21 /n

  • a = 10.8081 (6) Å

  • b = 17.6741 (12) Å

  • c = 18.8074 (13) Å

  • β = 101.292 (5)°

  • V = 3523.1 (4) Å3

  • Z = 8

  • Cu Kα radiation

  • μ = 2.08 mm−1

  • T = 296 K

  • 0.67 × 0.16 × 0.13 mm
Data collection

  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.338, Tmax = 0.771

  • 23827 measured reflections

  • 6634 independent reflections

  • 4034 reflections with I > 2σ(I)

  • Rint = 0.069
Refinement

  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.137

  • S = 0.92

  • 6634 reflections

  • 473 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N4A—H1N1⋯O1Bi 0.86 (3) 2.47 (3) 3.309 (3) 166 (3)
N1B—H1N3⋯O2Bii 0.84 (3) 2.44 (3) 3.219 (3) 155 (3)
C9A—H9AB⋯O1Bi 0.96 2.59 3.289 (3) 130
C16B—H16A⋯O1A 0.93 2.49 3.412 (3) 170
Symmetry codes: (i) x+1, y, z; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812008367/hb6653sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812008367/hb6653Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812008367/hb6653Isup3.cml

checkCIF report


Comment top

As part of our ongoing research on the bioactivity of hydrazones, the title compound (I) was synthesized in order to study and compare its biological activity with other related compounds (Chantrapromma et al., 2011; Fun et al., 2012; Abdel-Aziz & Mekawey, 2009; Abdel-Aziz et al., 2010). Herein we report the synthesis and crystal structure of (I).

The asymmetric unit of the title compound consists of two crystallographically independent molecules, (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 terminal phenyl rings (C1A–C6A)/(C11A–C16A) and (C1B–C6B)/(C11B–C16B) are 43.60 (12)° and 58.65 (13)° respectively. The hydrazine N atoms are twisted slightly out of the plane of the phenyl and carboxyphenyl rings, C1—N1—N2—C7 and N3—N4—C10—C11 torsion angles are 171.1 (2)° : -174.4 (2)° for molecule A and -177.4 (2)° : -170.6 (2)° for molecule B.

In the crystal, (Fig. 2), the molecules are linked via intermolecular N—H···O and C—H···O hydrogen bonds (Table 1), forming supramolecular chains along the b-axis.

Related literature top

For related structures and background to the bioactivity of hydrazones, see: Chantrapromma et al. (2011); Fun et al. (2012); Abdel-Aziz & Mekawey (2009); Abdel-Aziz et al. (2010). For reference bond lengths, see: Allen et al. (1987).

Experimental top

A mixture of 4-methoxybenzohydrazide (1.66 g, 10 mmol) and 2(Z)-2-oxo-N'-p-tolylpropanehydrazonoyl chloride (2.11 g, 10 mmol) in absolute ethanol (50 ml) was refluxed for 6 h. The concoction was then left to cool at room temperature. The formed solid was filtered off, washed with ethanol and recrystallized twice from EtOH to afford colourless blocks of the title compound.

Refinement top

Atoms H1N1 and H1N2 were located from a difference Fourier map and refined freely [N—H = 0.83 (3)–0.86 (3) Å]. The remaining H atoms were positioned geometrically [C—H = 0.93 or 0.96 Å] and were refined using a riding model, with Uiso(H) = 1.2 or 1.5Ueq(C). A rotating group model was applied to the methyl groups

Structure description top

As part of our ongoing research on the bioactivity of hydrazones, the title compound (I) was synthesized in order to study and compare its biological activity with other related compounds (Chantrapromma et al., 2011; Fun et al., 2012; Abdel-Aziz & Mekawey, 2009; Abdel-Aziz et al., 2010). Herein we report the synthesis and crystal structure of (I).

The asymmetric unit of the title compound consists of two crystallographically independent molecules, (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 terminal phenyl rings (C1A–C6A)/(C11A–C16A) and (C1B–C6B)/(C11B–C16B) are 43.60 (12)° and 58.65 (13)° respectively. The hydrazine N atoms are twisted slightly out of the plane of the phenyl and carboxyphenyl rings, C1—N1—N2—C7 and N3—N4—C10—C11 torsion angles are 171.1 (2)° : -174.4 (2)° for molecule A and -177.4 (2)° : -170.6 (2)° for molecule B.

In the crystal, (Fig. 2), the molecules are linked via intermolecular N—H···O and C—H···O hydrogen bonds (Table 1), forming supramolecular chains along the b-axis.

For related structures and background to the bioactivity of hydrazones, see: Chantrapromma et al. (2011); Fun et al. (2012); Abdel-Aziz & Mekawey (2009); Abdel-Aziz et al. (2010). For reference bond lengths, 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
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids. The C—-H···O hydrogen bond is shown by a dashed line.
[Figure 2] Fig. 2. The crystal packing of the title compound (I).
(1Z,2E)-N'-{2-chloro-1-methyl-2-[2-(4- methylphenyl)hydrazin-1-ylidene]ethylidene}-4-methoxybenzohydrazide top
Crystal data top
C18H19ClN4O2F(000) = 1504
Mr = 358.82Dx = 1.353 Mg m−3
Monoclinic, P21/nCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ynCell parameters from 682 reflections
a = 10.8081 (6) Åθ = 3.5–50.1°
b = 17.6741 (12) ŵ = 2.08 mm−1
c = 18.8074 (13) ÅT = 296 K
β = 101.292 (5)°Block, colourless
V = 3523.1 (4) Å30.67 × 0.16 × 0.13 mm
Z = 8
Data collection top
Bruker SMART APEXII CCD
diffractometer		6634 independent reflections
Radiation source: fine-focus sealed tube4034 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.069
φ and ω scansθmax = 70.8°, θmin = 3.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −11→12
Tmin = 0.338, Tmax = 0.771k = −20→21
23827 measured reflectionsl = −22→22
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H atoms treated by a mixture of independent and constrained refinement
S = 0.92 w = 1/[σ2(Fo2) + (0.0723P)2]
where P = (Fo2 + 2Fc2)/3
6634 reflections(Δ/σ)max < 0.001
473 parametersΔρmax = 0.21 e Å−3
0 restraintsΔρmin = −0.27 e Å−3
Crystal data top
C18H19ClN4O2V = 3523.1 (4) Å3
Mr = 358.82Z = 8
Monoclinic, P21/nCu Kα radiation
a = 10.8081 (6) ŵ = 2.08 mm−1
b = 17.6741 (12) ÅT = 296 K
c = 18.8074 (13) Å0.67 × 0.16 × 0.13 mm
β = 101.292 (5)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		6634 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		4034 reflections with I > 2σ(I)
Tmin = 0.338, Tmax = 0.771Rint = 0.069
23827 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.137H atoms treated by a mixture of independent and constrained refinement
S = 0.92Δρmax = 0.21 e Å−3
6634 reflectionsΔρmin = −0.27 e Å−3
473 parameters
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
xyzUiso*/Ueq
Cl1A0.58879 (6)0.16734 (5)0.05740 (4)0.0709 (2)
O1A0.59702 (17)0.04472 (13)0.26901 (10)0.0697 (6)
O2A0.93683 (19)−0.13626 (13)0.52739 (11)0.0733 (6)
N1A0.7147 (2)0.17038 (14)−0.06169 (12)0.0574 (6)
H1N20.651 (2)0.1952 (16)−0.0579 (13)0.055 (8)*
N2A0.77016 (17)0.12348 (13)−0.00915 (10)0.0495 (5)
N3A0.71923 (18)0.06453 (12)0.16041 (11)0.0505 (5)
N4A0.7690 (2)0.02089 (13)0.21952 (11)0.0505 (5)
H1N10.847 (3)0.0088 (17)0.2317 (15)0.073 (9)*
C1A0.7724 (2)0.18923 (15)−0.12007 (13)0.0483 (6)
C2A0.8838 (2)0.15662 (15)−0.12980 (13)0.0527 (6)
H2AA0.92190.1188−0.09870.063*
C3A0.9385 (2)0.18116 (16)−0.18688 (14)0.0554 (6)
H3AA1.01300.1587−0.19380.066*
C4A0.8849 (2)0.23833 (16)−0.23384 (13)0.0515 (6)
C5A0.7702 (2)0.26801 (16)−0.22403 (13)0.0542 (6)
H5AA0.73040.3050−0.25560.065*
C6A0.7146 (2)0.24337 (16)−0.16808 (13)0.0532 (6)
H6AA0.63740.2635−0.16270.064*
C7A0.7219 (2)0.11569 (15)0.04729 (13)0.0479 (6)
C8A0.7762 (2)0.06449 (14)0.10652 (12)0.0465 (6)
C9A0.8895 (2)0.01858 (17)0.09952 (13)0.0570 (7)
H9AA0.8792−0.03220.11540.086*
H9AB0.96350.04050.12890.086*
H9AC0.89870.01800.04980.086*
C10A0.7013 (2)0.01690 (16)0.27438 (13)0.0513 (6)
C11A0.7643 (2)−0.02482 (15)0.34023 (13)0.0482 (6)
C12A0.7512 (2)0.00365 (16)0.40728 (14)0.0564 (7)
H12A0.70360.04710.40950.068*
C13A0.8081 (2)−0.03193 (17)0.47067 (14)0.0592 (7)
H13B0.8001−0.01160.51520.071*
C14A0.8764 (2)−0.09732 (16)0.46832 (14)0.0548 (6)
C15A0.8862 (2)−0.12742 (16)0.40139 (15)0.0587 (7)
H15B0.9297−0.17250.39920.070*
C16A0.8320 (2)−0.09081 (16)0.33831 (14)0.0562 (6)
H16B0.8410−0.11080.29390.067*
C17A0.9474 (3)−0.1002 (2)0.59612 (14)0.0787 (9)
H17D1.0058−0.12770.63190.118*
H17E0.8662−0.09910.60960.118*
H17F0.9773−0.04930.59310.118*
C18A0.9478 (3)0.26841 (18)−0.29298 (14)0.0653 (8)
H18A1.02170.2389−0.29480.098*
H18B0.97150.3203−0.28300.098*
H18C0.89020.2652−0.33880.098*
Cl1B0.09492 (6)0.17833 (4)0.06847 (4)0.0690 (2)
O1B0.08021 (16)0.00658 (13)0.25845 (10)0.0677 (6)
O2B0.41947 (16)−0.15836 (11)0.52262 (9)0.0593 (5)
N1B0.2306 (2)0.18981 (14)−0.04787 (11)0.0561 (6)
H1N30.175 (3)0.2186 (17)−0.0381 (15)0.063 (9)*
N2B0.27462 (18)0.13522 (12)−0.00049 (10)0.0488 (5)
N3B0.21195 (19)0.06202 (12)0.16206 (11)0.0522 (5)
N4B0.2637 (2)0.01366 (14)0.21748 (11)0.0553 (6)
H1N40.341 (3)0.0023 (16)0.2249 (14)0.062 (9)*
C1B0.2828 (2)0.20065 (16)−0.11030 (12)0.0483 (6)
C2B0.3676 (2)0.15036 (16)−0.13001 (13)0.0552 (6)
H2BA0.39470.1085−0.10120.066*
C3B0.4121 (2)0.16293 (17)−0.19348 (14)0.0588 (7)
H3BA0.46900.1288−0.20670.071*
C4B0.3744 (2)0.22483 (17)−0.23770 (13)0.0565 (7)
C5B0.2889 (2)0.27408 (16)−0.21659 (14)0.0585 (7)
H5BA0.26120.3158−0.24540.070*
C6B0.2436 (2)0.26265 (16)−0.15338 (14)0.0567 (7)
H6BA0.18680.2968−0.14000.068*
C7B0.2228 (2)0.12438 (15)0.05462 (12)0.0468 (6)
C8B0.2722 (2)0.06806 (14)0.10995 (12)0.0476 (6)
C9B0.3883 (2)0.02446 (16)0.10250 (13)0.0555 (6)
H9BA0.3783−0.02760.11490.083*
H9BB0.46030.04540.13450.083*
H9BC0.40040.02770.05340.083*
C10B0.1923 (2)−0.00721 (16)0.26657 (13)0.0518 (6)
C11B0.2620 (2)−0.04923 (15)0.33097 (13)0.0486 (6)
C12B0.1914 (2)−0.09340 (17)0.36911 (13)0.0574 (7)
H12B0.1050−0.09830.35190.069*
C13B0.2459 (2)−0.13004 (17)0.43162 (14)0.0576 (7)
H13A0.1969−0.15990.45600.069*
C14B0.3738 (2)−0.12254 (15)0.45834 (13)0.0492 (6)
C15B0.4464 (2)−0.08009 (17)0.42068 (14)0.0581 (7)
H15A0.5330−0.07590.43770.070*
C16B0.3900 (2)−0.04350 (17)0.35718 (14)0.0568 (7)
H16A0.4392−0.01470.33200.068*
C17B0.5505 (3)−0.1523 (2)0.55176 (16)0.0784 (9)
H17A0.5692−0.17730.59790.118*
H17B0.5734−0.09990.55780.118*
H17C0.5973−0.17570.51930.118*
C18B0.4217 (3)0.2380 (2)−0.30722 (15)0.0816 (10)
H18D0.45580.2882−0.30700.122*
H18E0.35320.2325−0.34790.122*
H18F0.48630.2017−0.31090.122*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0695 (4)0.0784 (5)0.0718 (5)0.0242 (4)0.0307 (3)0.0255 (4)
O1A0.0578 (11)0.0935 (16)0.0601 (12)0.0181 (10)0.0175 (8)0.0240 (11)
O2A0.0848 (13)0.0767 (15)0.0551 (12)0.0137 (11)0.0054 (9)0.0151 (11)
N1A0.0499 (11)0.0721 (17)0.0515 (13)0.0102 (11)0.0131 (9)0.0200 (11)
N2A0.0478 (10)0.0576 (13)0.0422 (11)0.0008 (9)0.0068 (8)0.0061 (10)
N3A0.0555 (11)0.0506 (13)0.0446 (12)0.0016 (10)0.0079 (9)0.0083 (10)
N4A0.0516 (12)0.0569 (14)0.0430 (12)0.0031 (10)0.0091 (9)0.0081 (10)
C1A0.0472 (12)0.0531 (15)0.0433 (13)−0.0045 (11)0.0056 (9)0.0046 (11)
C2A0.0588 (14)0.0521 (15)0.0471 (14)0.0058 (12)0.0099 (11)0.0087 (12)
C3A0.0561 (13)0.0606 (17)0.0509 (15)0.0065 (12)0.0137 (11)0.0020 (13)
C4A0.0555 (13)0.0576 (16)0.0407 (14)−0.0070 (12)0.0083 (10)−0.0016 (12)
C5A0.0548 (13)0.0588 (17)0.0455 (14)−0.0013 (12)0.0012 (10)0.0088 (12)
C6A0.0457 (12)0.0640 (17)0.0491 (15)−0.0002 (12)0.0069 (10)0.0071 (13)
C7A0.0476 (12)0.0491 (15)0.0469 (14)−0.0040 (10)0.0087 (10)0.0025 (11)
C8A0.0450 (11)0.0503 (15)0.0435 (14)−0.0040 (10)0.0068 (9)0.0008 (11)
C9A0.0544 (14)0.0682 (19)0.0479 (15)0.0111 (13)0.0085 (11)0.0093 (13)
C10A0.0528 (14)0.0556 (16)0.0465 (15)−0.0035 (12)0.0119 (10)0.0077 (12)
C11A0.0469 (12)0.0524 (15)0.0459 (14)−0.0033 (11)0.0109 (10)0.0038 (12)
C12A0.0585 (14)0.0602 (17)0.0517 (16)0.0089 (12)0.0137 (11)0.0048 (13)
C13A0.0667 (16)0.0651 (19)0.0457 (15)0.0036 (13)0.0111 (12)0.0011 (13)
C14A0.0553 (13)0.0592 (17)0.0475 (15)−0.0024 (12)0.0047 (10)0.0120 (13)
C15A0.0618 (15)0.0535 (16)0.0625 (17)0.0078 (13)0.0166 (12)0.0056 (14)
C16A0.0628 (15)0.0578 (17)0.0502 (15)0.0012 (13)0.0168 (11)0.0026 (13)
C17A0.0810 (19)0.098 (3)0.0509 (17)−0.0136 (18)−0.0027 (13)0.0153 (18)
C18A0.0745 (17)0.075 (2)0.0491 (16)−0.0029 (15)0.0174 (13)0.0100 (14)
Cl1B0.0718 (4)0.0765 (5)0.0656 (4)0.0235 (4)0.0301 (3)0.0240 (4)
O1B0.0534 (11)0.0966 (17)0.0523 (11)0.0068 (10)0.0081 (8)0.0212 (11)
O2B0.0651 (10)0.0595 (12)0.0490 (10)−0.0014 (9)0.0000 (8)0.0135 (9)
N1B0.0602 (13)0.0623 (15)0.0488 (13)0.0139 (11)0.0186 (10)0.0140 (11)
N2B0.0524 (10)0.0527 (13)0.0403 (11)0.0001 (9)0.0066 (8)0.0068 (10)
N3B0.0573 (11)0.0568 (14)0.0418 (11)0.0023 (10)0.0078 (9)0.0102 (10)
N4B0.0564 (13)0.0655 (15)0.0442 (12)0.0070 (11)0.0102 (9)0.0125 (11)
C1B0.0458 (12)0.0575 (16)0.0412 (13)−0.0009 (11)0.0073 (9)0.0064 (12)
C2B0.0558 (13)0.0615 (17)0.0475 (15)0.0057 (12)0.0083 (11)0.0111 (13)
C3B0.0536 (13)0.0712 (19)0.0532 (16)0.0059 (13)0.0142 (11)−0.0004 (14)
C4B0.0501 (13)0.075 (2)0.0443 (14)−0.0069 (13)0.0098 (10)0.0067 (13)
C5B0.0628 (15)0.0601 (18)0.0531 (16)−0.0020 (13)0.0127 (12)0.0158 (13)
C6B0.0614 (15)0.0561 (17)0.0545 (16)0.0039 (12)0.0164 (12)0.0081 (13)
C7B0.0458 (12)0.0499 (15)0.0441 (13)0.0010 (10)0.0073 (10)0.0026 (11)
C8B0.0512 (12)0.0474 (14)0.0419 (13)−0.0050 (11)0.0033 (10)0.0006 (11)
C9B0.0599 (14)0.0603 (17)0.0460 (15)0.0044 (12)0.0097 (11)0.0064 (13)
C10B0.0573 (15)0.0569 (16)0.0420 (14)−0.0014 (12)0.0120 (10)0.0016 (12)
C11B0.0515 (13)0.0531 (15)0.0405 (13)−0.0023 (11)0.0074 (10)0.0058 (11)
C12B0.0476 (13)0.0711 (19)0.0523 (15)−0.0068 (12)0.0068 (10)0.0112 (14)
C13B0.0561 (14)0.0641 (18)0.0525 (16)−0.0101 (13)0.0103 (11)0.0147 (13)
C14B0.0569 (13)0.0458 (14)0.0439 (14)0.0028 (11)0.0074 (10)0.0045 (11)
C15B0.0459 (12)0.0696 (19)0.0566 (16)−0.0009 (12)0.0044 (10)0.0108 (14)
C16B0.0523 (13)0.0661 (18)0.0526 (15)−0.0048 (12)0.0118 (11)0.0141 (13)
C17B0.0720 (17)0.082 (2)0.070 (2)−0.0016 (16)−0.0129 (14)0.0232 (18)
C18B0.0762 (19)0.116 (3)0.0565 (18)0.0018 (19)0.0232 (14)0.0198 (19)
Geometric parameters (Å, º) top
Cl1A—C7A1.745 (2)Cl1B—C7B1.740 (2)
O1A—C10A1.216 (3)O1B—C10B1.216 (3)
O2A—C14A1.360 (3)O2B—C14B1.368 (3)
O2A—C17A1.426 (3)O2B—C17B1.418 (3)
N1A—N2A1.338 (3)N1B—N2B1.336 (3)
N1A—C1A1.405 (3)N1B—C1B1.412 (3)
N1A—H1N20.83 (3)N1B—H1N30.83 (3)
N2A—C7A1.279 (3)N2B—C7B1.285 (3)
N3A—C8A1.285 (3)N3B—C8B1.283 (3)
N3A—N4A1.373 (3)N3B—N4B1.379 (3)
N4A—C10A1.378 (3)N4B—C10B1.365 (3)
N4A—H1N10.86 (3)N4B—H1N40.84 (3)
C1A—C2A1.379 (3)C1B—C2B1.379 (3)
C1A—C6A1.379 (3)C1B—C6B1.379 (4)
C2A—C3A1.392 (3)C2B—C3B1.390 (3)
C2A—H2AA0.9300C2B—H2BA0.9300
C3A—C4A1.391 (4)C3B—C4B1.386 (4)
C3A—H3AA0.9300C3B—H3BA0.9300
C4A—C5A1.391 (4)C4B—C5B1.383 (4)
C4A—C18A1.510 (3)C4B—C18B1.513 (3)
C5A—C6A1.381 (3)C5B—C6B1.386 (3)
C5A—H5AA0.9300C5B—H5BA0.9300
C6A—H6AA0.9300C6B—H6BA0.9300
C7A—C8A1.466 (3)C7B—C8B1.463 (3)
C8A—C9A1.496 (3)C8B—C9B1.502 (3)
C9A—H9AA0.9600C9B—H9BA0.9600
C9A—H9AB0.9600C9B—H9BB0.9600
C9A—H9AC0.9600C9B—H9BC0.9600
C10A—C11A1.487 (3)C10B—C11B1.493 (3)
C11A—C16A1.381 (4)C11B—C16B1.378 (3)
C11A—C12A1.391 (3)C11B—C12B1.386 (3)
C12A—C13A1.381 (3)C12B—C13B1.370 (3)
C12A—H12A0.9300C12B—H12B0.9300
C13A—C14A1.377 (4)C13B—C14B1.382 (3)
C13A—H13B0.9300C13B—H13A0.9300
C14A—C15A1.390 (4)C14B—C15B1.378 (3)
C15A—C16A1.378 (4)C15B—C16B1.390 (3)
C15A—H15B0.9300C15B—H15A0.9300
C16A—H16B0.9300C16B—H16A0.9300
C17A—H17D0.9600C17B—H17A0.9600
C17A—H17E0.9600C17B—H17B0.9600
C17A—H17F0.9600C17B—H17C0.9600
C18A—H18A0.9600C18B—H18D0.9600
C18A—H18B0.9600C18B—H18E0.9600
C18A—H18C0.9600C18B—H18F0.9600
C14A—O2A—C17A117.0 (2)C14B—O2B—C17B117.8 (2)
N2A—N1A—C1A121.4 (2)N2B—N1B—C1B120.3 (2)
N2A—N1A—H1N2121.4 (18)N2B—N1B—H1N3118.0 (19)
C1A—N1A—H1N2116.4 (18)C1B—N1B—H1N3121.5 (19)
C7A—N2A—N1A118.9 (2)C7B—N2B—N1B119.4 (2)
C8A—N3A—N4A117.8 (2)C8B—N3B—N4B115.9 (2)
N3A—N4A—C10A117.0 (2)C10B—N4B—N3B118.6 (2)
N3A—N4A—H1N1125 (2)C10B—N4B—H1N4119.8 (18)
C10A—N4A—H1N1115.1 (19)N3B—N4B—H1N4121.0 (19)
C2A—C1A—C6A119.9 (2)C2B—C1B—C6B119.9 (2)
C2A—C1A—N1A122.5 (2)C2B—C1B—N1B122.1 (2)
C6A—C1A—N1A117.6 (2)C6B—C1B—N1B118.0 (2)
C1A—C2A—C3A119.0 (2)C1B—C2B—C3B119.2 (2)
C1A—C2A—H2AA120.5C1B—C2B—H2BA120.4
C3A—C2A—H2AA120.5C3B—C2B—H2BA120.4
C4A—C3A—C2A121.9 (2)C4B—C3B—C2B122.0 (3)
C4A—C3A—H3AA119.0C4B—C3B—H3BA119.0
C2A—C3A—H3AA119.0C2B—C3B—H3BA119.0
C5A—C4A—C3A117.4 (2)C5B—C4B—C3B117.3 (2)
C5A—C4A—C18A120.4 (2)C5B—C4B—C18B120.6 (3)
C3A—C4A—C18A122.1 (2)C3B—C4B—C18B122.0 (3)
C6A—C5A—C4A121.0 (2)C4B—C5B—C6B121.5 (3)
C6A—C5A—H5AA119.5C4B—C5B—H5BA119.3
C4A—C5A—H5AA119.5C6B—C5B—H5BA119.3
C1A—C6A—C5A120.6 (2)C1B—C6B—C5B120.0 (3)
C1A—C6A—H6AA119.7C1B—C6B—H6BA120.0
C5A—C6A—H6AA119.7C5B—C6B—H6BA120.0
N2A—C7A—C8A122.0 (2)N2B—C7B—C8B121.2 (2)
N2A—C7A—Cl1A120.9 (2)N2B—C7B—Cl1B121.56 (19)
C8A—C7A—Cl1A117.15 (16)C8B—C7B—Cl1B117.15 (17)
N3A—C8A—C7A114.6 (2)N3B—C8B—C7B115.5 (2)
N3A—C8A—C9A126.6 (2)N3B—C8B—C9B125.9 (2)
C7A—C8A—C9A118.8 (2)C7B—C8B—C9B118.6 (2)
C8A—C9A—H9AA109.5C8B—C9B—H9BA109.5
C8A—C9A—H9AB109.5C8B—C9B—H9BB109.5
H9AA—C9A—H9AB109.5H9BA—C9B—H9BB109.5
C8A—C9A—H9AC109.5C8B—C9B—H9BC109.5
H9AA—C9A—H9AC109.5H9BA—C9B—H9BC109.5
H9AB—C9A—H9AC109.5H9BB—C9B—H9BC109.5
O1A—C10A—N4A122.4 (2)O1B—C10B—N4B122.9 (2)
O1A—C10A—C11A122.4 (2)O1B—C10B—C11B122.3 (2)
N4A—C10A—C11A115.2 (2)N4B—C10B—C11B114.9 (2)
C16A—C11A—C12A118.5 (2)C16B—C11B—C12B118.2 (2)
C16A—C11A—C10A123.8 (2)C16B—C11B—C10B124.5 (2)
C12A—C11A—C10A117.7 (2)C12B—C11B—C10B117.3 (2)
C13A—C12A—C11A120.7 (3)C13B—C12B—C11B121.5 (2)
C13A—C12A—H12A119.6C13B—C12B—H12B119.3
C11A—C12A—H12A119.6C11B—C12B—H12B119.3
C14A—C13A—C12A120.3 (2)C12B—C13B—C14B119.9 (2)
C14A—C13A—H13B119.8C12B—C13B—H13A120.1
C12A—C13A—H13B119.8C14B—C13B—H13A120.1
O2A—C14A—C13A125.0 (3)O2B—C14B—C15B124.3 (2)
O2A—C14A—C15A115.9 (3)O2B—C14B—C13B116.0 (2)
C13A—C14A—C15A119.2 (2)C15B—C14B—C13B119.7 (2)
C16A—C15A—C14A120.3 (3)C14B—C15B—C16B119.8 (2)
C16A—C15A—H15B119.8C14B—C15B—H15A120.1
C14A—C15A—H15B119.8C16B—C15B—H15A120.1
C15A—C16A—C11A120.8 (2)C11B—C16B—C15B121.0 (2)
C15A—C16A—H16B119.6C11B—C16B—H16A119.5
C11A—C16A—H16B119.6C15B—C16B—H16A119.5
O2A—C17A—H17D109.5O2B—C17B—H17A109.5
O2A—C17A—H17E109.5O2B—C17B—H17B109.5
H17D—C17A—H17E109.5H17A—C17B—H17B109.5
O2A—C17A—H17F109.5O2B—C17B—H17C109.5
H17D—C17A—H17F109.5H17A—C17B—H17C109.5
H17E—C17A—H17F109.5H17B—C17B—H17C109.5
C4A—C18A—H18A109.5C4B—C18B—H18D109.5
C4A—C18A—H18B109.5C4B—C18B—H18E109.5
H18A—C18A—H18B109.5H18D—C18B—H18E109.5
C4A—C18A—H18C109.5C4B—C18B—H18F109.5
H18A—C18A—H18C109.5H18D—C18B—H18F109.5
H18B—C18A—H18C109.5H18E—C18B—H18F109.5
C1A—N1A—N2A—C7A171.1 (2)C1B—N1B—N2B—C7B−177.4 (2)
C8A—N3A—N4A—C10A−175.0 (2)C8B—N3B—N4B—C10B−166.8 (2)
N2A—N1A—C1A—C2A5.0 (4)N2B—N1B—C1B—C2B8.8 (4)
N2A—N1A—C1A—C6A−174.0 (2)N2B—N1B—C1B—C6B−173.2 (2)
C6A—C1A—C2A—C3A2.3 (4)C6B—C1B—C2B—C3B−0.2 (4)
N1A—C1A—C2A—C3A−176.7 (3)N1B—C1B—C2B—C3B177.8 (3)
C1A—C2A—C3A—C4A0.9 (4)C1B—C2B—C3B—C4B0.3 (4)
C2A—C3A—C4A—C5A−3.1 (4)C2B—C3B—C4B—C5B−0.5 (4)
C2A—C3A—C4A—C18A176.2 (3)C2B—C3B—C4B—C18B−179.3 (3)
C3A—C4A—C5A—C6A2.3 (4)C3B—C4B—C5B—C6B0.7 (4)
C18A—C4A—C5A—C6A−177.0 (3)C18B—C4B—C5B—C6B179.5 (3)
C2A—C1A—C6A—C5A−3.1 (4)C2B—C1B—C6B—C5B0.4 (4)
N1A—C1A—C6A—C5A175.9 (3)N1B—C1B—C6B—C5B−177.7 (3)
C4A—C5A—C6A—C1A0.8 (4)C4B—C5B—C6B—C1B−0.6 (4)
N1A—N2A—C7A—C8A179.1 (2)N1B—N2B—C7B—C8B−176.6 (2)
N1A—N2A—C7A—Cl1A−2.0 (3)N1B—N2B—C7B—Cl1B0.9 (3)
N4A—N3A—C8A—C7A−176.6 (2)N4B—N3B—C8B—C7B−174.9 (2)
N4A—N3A—C8A—C9A3.0 (4)N4B—N3B—C8B—C9B3.5 (4)
N2A—C7A—C8A—N3A178.0 (2)N2B—C7B—C8B—N3B−179.5 (2)
Cl1A—C7A—C8A—N3A−0.9 (3)Cl1B—C7B—C8B—N3B2.9 (3)
N2A—C7A—C8A—C9A−1.7 (4)N2B—C7B—C8B—C9B2.0 (4)
Cl1A—C7A—C8A—C9A179.34 (19)Cl1B—C7B—C8B—C9B−175.62 (19)
N3A—N4A—C10A—O1A6.4 (4)N3B—N4B—C10B—O1B10.0 (4)
N3A—N4A—C10A—C11A−174.4 (2)N3B—N4B—C10B—C11B−170.6 (2)
O1A—C10A—C11A—C16A138.9 (3)O1B—C10B—C11B—C16B−155.4 (3)
N4A—C10A—C11A—C16A−40.3 (4)N4B—C10B—C11B—C16B25.3 (4)
O1A—C10A—C11A—C12A−39.5 (4)O1B—C10B—C11B—C12B20.7 (4)
N4A—C10A—C11A—C12A141.4 (2)N4B—C10B—C11B—C12B−158.7 (2)
C16A—C11A—C12A—C13A2.1 (4)C16B—C11B—C12B—C13B0.6 (4)
C10A—C11A—C12A—C13A−179.5 (2)C10B—C11B—C12B—C13B−175.7 (3)
C11A—C12A—C13A—C14A−1.5 (4)C11B—C12B—C13B—C14B0.8 (4)
C17A—O2A—C14A—C13A−10.8 (4)C17B—O2B—C14B—C15B−1.1 (4)
C17A—O2A—C14A—C15A169.2 (2)C17B—O2B—C14B—C13B179.7 (3)
C12A—C13A—C14A—O2A179.4 (3)C12B—C13B—C14B—O2B177.3 (3)
C12A—C13A—C14A—C15A−0.7 (4)C12B—C13B—C14B—C15B−2.0 (4)
O2A—C14A—C15A—C16A−177.8 (2)O2B—C14B—C15B—C16B−177.5 (3)
C13A—C14A—C15A—C16A2.2 (4)C13B—C14B—C15B—C16B1.7 (4)
C14A—C15A—C16A—C11A−1.6 (4)C12B—C11B—C16B—C15B−0.9 (4)
C12A—C11A—C16A—C15A−0.6 (4)C10B—C11B—C16B—C15B175.1 (3)
C10A—C11A—C16A—C15A−178.9 (2)C14B—C15B—C16B—C11B−0.3 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4A—H1N1···O1Bi0.86 (3)2.47 (3)3.309 (3)166 (3)
N1B—H1N3···O2Bii0.84 (3)2.44 (3)3.219 (3)155 (3)
C9A—H9AB···O1Bi0.962.593.289 (3)130
C16B—H16A···O1A0.932.493.412 (3)170
Symmetry codes: (i) x+1, y, z; (ii) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC18H19ClN4O2
Mr358.82
Crystal system, space groupMonoclinic, P21/n
Temperature (K)296
a, b, c (Å)10.8081 (6), 17.6741 (12), 18.8074 (13)
β (°) 101.292 (5)
V (Å3)3523.1 (4)
Z8
Radiation typeCu Kα
µ (mm−1)2.08
Crystal size (mm)0.67 × 0.16 × 0.13
Data collection
DiffractometerBruker SMART APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.338, 0.771
No. of measured, independent and
observed [I > 2σ(I)] reflections		23827, 6634, 4034
Rint0.069
(sin θ/λ)max (Å−1)0.613
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.137, 0.92
No. of reflections6634
No. of parameters473
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.21, −0.27

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4A—H1N1···O1Bi0.86 (3)2.47 (3)3.309 (3)166 (3)
N1B—H1N3···O2Bii0.84 (3)2.44 (3)3.219 (3)155 (3)
C9A—H9AB···O1Bi0.962.593.289 (3)130
C16B—H16A···O1A0.932.493.412 (3)170
Symmetry codes: (i) x+1, y, z; (ii) −x+1/2, y+1/2, −z+1/2.
 

Footnotes

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

Acknowledgements

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 Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a postdoctoral research fellowship.

References

First citationAbdel-Aziz, H. A., Abdel-Wahab, B. F. & Badria, F. A. (2010). Arch. Pharm. 343, 152–159.  Google Scholar
 First citationAbdel-Aziz, H. A. & Mekawey, A. A. I. (2009). Eur. J. Med. Chem. 44, 3985–4997.  Google Scholar
 First citationAllen, 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
 First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationChantrapromma, S., Nilwanna, B., Jansrisewangwong, P., Kobkeatthawin, T. & Fun, H.-K. (2011). Acta Cryst. E67, o3499–o3500.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationFun, H.-K., Nilwanna, B., Chantrapromma, S. & Razak, I. A. (2012). Acta Cryst. E68, o398–o399.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 68| Part 4| April 2012| Page o926
doi:10.1107/S1600536812008367
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