(N′,N′′Z,N′,N′′E)-N′,N′′-[1-(4-Chloro­phen­yl)ethane-1,2-diyl­idene]bis­(3-methyl-1-benzofuran-2-carbohydrazide)

Fun, H.-K.; Chia, T.S.; Alafeefy, A.M.; Abdel-Aziz, H.A.

doi:10.1107/S1600536812030504

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Pages o2405-o2406

https://doi.org/10.1107/S1600536812030504

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(N′,N′′Z,N′,N′′E)-N′,N′′-[1-(4-Chlorophenyl)ethane-1,2-diylidene]bis(3-methyl-1-benzofuran-2-carbohydrazide)

Hoong-Kun Fun,^a ^*‡ Tze Shyang Chia,^a Ahmed M. Alafeefy ^b and Hatem A. Abdel-Aziz ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Pharmaceutical Chemistry, College of Pharmacy, Salman Bin Abdulaziz University, PO Box 173, Alkharj 11942, Saudi Arabia, and ^cDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia
^*Correspondence e-mail: hkfun@usm.my

(Received 3 July 2012; accepted 4 July 2012; online 10 July 2012)

In the title compound, C₂₈H₂₁ClN₄O₄, the benzofuran ring systems make dihedral angles of 7.43 (8) and 30.92 (9)° with the chloro-substituted benzene ring. The dihedral angle between the two benzofuran ring systems is 27.41 (7)°. The two benzofuran rings are connected to the chloro-substituted benzene ring through C—N—N=C and C—N—N=C—C bridges which are nearly planar [maximum deviations = 0.003 (1) and 0.037 (1) Å]. An intramolecular N—H⋯N hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked by N—H⋯(O,N) and C—H⋯O hydrogen bonds into a tape along the c axis and these tapes are further connected by another weak C—H⋯O hydrogen bond into a sheet parallel to the bc plane. π–π interactions [centroid-to-centroid distances = 3.4845 (12)–3.6250 (13) Å] are also observed.

Related literature

For the biological activity of benzofurans, see: Abdel-Aziz et al. (2009 ); Abdel-Aziz & Mekawey (2009 ); Abdel-Wahab et al. (2009 ); Bhovi et al. (2010 ). For the synthesis, see: Abdel-Aziz et al. (2009). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₈H₂₁ClN₄O₄
M_r = 512.94
Monoclinic, P 2₁ /c
a = 7.5539 (9) Å
b = 23.332 (3) Å
c = 13.6027 (16) Å
β = 94.275 (2)°
V = 2390.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 100 K
0.30 × 0.11 × 0.09 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.942, T_max = 0.983
19379 measured reflections
6850 independent reflections
4662 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.144
S = 1.03
6850 reflections
344 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯N3	0.89 (2)	1.96 (2)	2.644 (2)	132.3 (18)
N4—H1N4⋯O2ⁱ	0.95 (3)	2.31 (3)	3.187 (2)	154 (2)
N4—H1N4⋯N2ⁱ	0.95 (3)	2.48 (3)	3.205 (2)	134 (2)
C17—H17A⋯O2ⁱ	0.93	2.32	3.165 (2)	150
C28—H28C⋯O4ⁱⁱ	0.96	2.53	3.464 (2)	164
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x, -y+2, -z+1.

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: https://doi.org/10.1107/S1600536812030504/is5163sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812030504/is5163Isup2.hkl

checkCIF report

Comment top

Benzofurans are found to be useful as anticonvulsant, anti-inflammatory, antitumor, antifungal, anthelmintic and antihyperglycemic agents (Abdel-Aziz et al., 2009; Abdel-Aziz & Mekawey, 2009; Abdel-Wahab et al., 2009; Bhovi et al., 2010). In view of the biological activities and in continuation to our interest with benzofurans, we report herein the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The O1/C1–C8 and O3/C19–C26 benzofuran ring systems (r.m.s. deviations = 0.0096 and 0.0052 Å, respectively) make dihedral angles of 7.43 (8) and 30.92 (9)°, respectively with the chloro-substituted C11–C16 benzene ring. The dihedral angle between the two benzofuran ring systems is 27.41 (7)°. The two benzofuran rings are connected to the chloro-substituted benzene ring through C9—N1—N2—C10 and C18—N4—N3—C17—C10 bridges which are nearly planar [maximum deviations = 0.003 (1) Å at atom N2 and 0.037 (1) Å at atom C17] and the ketone O2 and O4 atoms are almost coplanar with their attached bridges [N2—N1—C9—O2 = 0.1 (3)° and N3—N4—C18—O4 = 11.4 (3)°]. An intramolecular N1—H1N1···N3 hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995) in the molecule.

In the crystal (Fig. 2), the molecules are linked by N4—H1N4···(O2,N2) and C17—H17A···O2 hydrogen bonds (Table 1) into a tape along the c axis and the tapes are further connected by weak C28—H28C···O4 hydrogen bonds into a sheet parallel to the bc plane. π–π interactions are also observed with Cg1···Cg3 = 3.4845 (12) Å [-x, 2 - y, 1 - z], Cg2···Cg4 = 3.6250 (13) Å [-1 + x, 3/2 - y, -1/2 + z] and Cg3···Cg3 = 3.6124 (13) Å [-1 - x, 2 - y, 1 - z], where Cg1, Cg2, Cg3 and Cg4 are the centroids of O1/C1/C6–C8, O3/C19–C21/C26, C1–C6 and C11–C16 rings, respectively.

Related literature top

For the biological activity of benzofurans, see: Abdel-Aziz et al. (2009); Abdel-Aziz & Mekawey (2009); Abdel-Wahab et al. (2009); Bhovi et al. (2010). For the synthesis, see: Abdel-Aziz et al. (2009). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound was prepared by the reaction of 3-methylbenzofuran-2-carbohydrazide with 2-chloro-1-(4-chlorophenyl)ethanone in absolute ethanol according to the reported method (Abdel-Aziz et al., 2009). Colourless blocks suitable for an X-ray structural analysis were obtained by slow evaporation from EtOH/DMF.

Structure description top

For the biological activity of benzofurans, see: Abdel-Aziz et al. (2009); Abdel-Aziz & Mekawey (2009); Abdel-Wahab et al. (2009); Bhovi et al. (2010). For the synthesis, see: Abdel-Aziz et al. (2009). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

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 molecular structure of the title compound with atom labels and 50% probability displacement ellipsoids. The dashed line represents the intramolecular N—H···N hydrogen bond.
	Fig. 2. The crystal packing of the title compound. The dashed lines represent the hydrogen bonds. For sake of clarity, hydrogen atoms not involved in hydrogen bonding have been omitted.

(N',N''Z,N',N''E)- N',N''-[1-(4-Chlorophenyl)ethane-1,2-diylidene]bis(3- methyl-1-benzofuran-2-carbohydrazide) top

Crystal data top

C₂₈H₂₁ClN₄O₄	F(000) = 1064
M_r = 512.94	D_x = 1.425 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4684 reflections
a = 7.5539 (9) Å	θ = 2.3–29.8°
b = 23.332 (3) Å	µ = 0.20 mm⁻¹
c = 13.6027 (16) Å	T = 100 K
β = 94.275 (2)°	Block, colourless
V = 2390.8 (5) Å³	0.30 × 0.11 × 0.09 mm
Z = 4

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	6850 independent reflections
Radiation source: fine-focus sealed tube	4662 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
φ and ω scans	θ_max = 29.9°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→10
T_min = 0.942, T_max = 0.983	k = −32→28
19379 measured reflections	l = −18→18

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0696P)² + 0.8585P] where P = (F_o² + 2F_c²)/3
6850 reflections	(Δ/σ)_max = 0.001
344 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₂₈H₂₁ClN₄O₄	V = 2390.8 (5) Å³
M_r = 512.94	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.5539 (9) Å	µ = 0.20 mm⁻¹
b = 23.332 (3) Å	T = 100 K
c = 13.6027 (16) Å	0.30 × 0.11 × 0.09 mm
β = 94.275 (2)°

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	6850 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4662 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.983	R_int = 0.043
19379 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.36 e Å⁻³
6850 reflections	Δρ_min = −0.49 e Å⁻³
344 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 100.0 (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
Cl1	0.45030 (7)	0.51063 (2)	0.65612 (4)	0.02517 (13)
O1	−0.18297 (18)	0.91093 (5)	0.50974 (9)	0.0174 (3)
O2	0.0296 (2)	0.84287 (6)	0.72023 (9)	0.0260 (3)
O3	−0.26774 (18)	0.77075 (5)	0.10805 (9)	0.0182 (3)
O4	−0.1284 (2)	0.88213 (6)	0.27065 (10)	0.0275 (3)
N1	0.0177 (2)	0.81923 (6)	0.55642 (11)	0.0161 (3)
N2	0.1004 (2)	0.76847 (6)	0.57851 (11)	0.0161 (3)
N3	0.0059 (2)	0.78780 (7)	0.36930 (10)	0.0175 (3)
N4	−0.0473 (2)	0.78768 (7)	0.27125 (11)	0.0190 (3)
C1	−0.2346 (2)	0.96694 (8)	0.49610 (13)	0.0166 (4)
C2	−0.3267 (3)	0.98844 (8)	0.41213 (14)	0.0207 (4)
H2A	−0.3607	0.9653	0.3583	0.025*
C3	−0.3650 (3)	1.04656 (9)	0.41339 (15)	0.0238 (4)
H3A	−0.4277	1.0631	0.3591	0.029*
C4	−0.3112 (3)	1.08106 (9)	0.49488 (15)	0.0242 (4)
H4A	−0.3386	1.1199	0.4930	0.029*
C5	−0.2186 (3)	1.05869 (8)	0.57782 (15)	0.0211 (4)
H5A	−0.1820	1.0820	0.6310	0.025*
C6	−0.1818 (2)	0.99973 (8)	0.57888 (13)	0.0168 (4)
C7	−0.0928 (2)	0.96115 (8)	0.64901 (13)	0.0171 (4)
C8	−0.0978 (2)	0.90913 (8)	0.60363 (12)	0.0167 (4)
C9	−0.0134 (3)	0.85473 (8)	0.63364 (12)	0.0174 (4)
C10	0.1336 (2)	0.73377 (7)	0.50707 (12)	0.0154 (3)
C11	0.2211 (2)	0.67909 (8)	0.53963 (13)	0.0157 (3)
C12	0.2970 (3)	0.67412 (8)	0.63637 (13)	0.0212 (4)
H12A	0.3000	0.7059	0.6776	0.025*
C13	0.3677 (3)	0.62277 (8)	0.67172 (14)	0.0225 (4)
H13A	0.4167	0.6200	0.7363	0.027*
C14	0.3648 (3)	0.57558 (8)	0.60979 (14)	0.0195 (4)
C15	0.2966 (3)	0.57942 (8)	0.51350 (14)	0.0232 (4)
H15A	0.2980	0.5477	0.4721	0.028*
C16	0.2252 (3)	0.63126 (8)	0.47841 (14)	0.0205 (4)
H16A	0.1796	0.6340	0.4132	0.025*
C17	0.0845 (3)	0.74172 (8)	0.40184 (13)	0.0186 (4)
H17A	0.1104	0.7130	0.3576	0.022*
C18	−0.1258 (3)	0.83580 (8)	0.22966 (13)	0.0180 (4)
C19	−0.2064 (2)	0.82603 (8)	0.12888 (13)	0.0168 (4)
C20	−0.2279 (3)	0.86146 (8)	0.04978 (13)	0.0172 (4)
C21	−0.3092 (3)	0.82657 (8)	−0.02879 (13)	0.0188 (4)
C22	−0.3632 (3)	0.83616 (9)	−0.12821 (14)	0.0266 (4)
H22A	−0.3489	0.8719	−0.1570	0.032*
C23	−0.4381 (3)	0.79104 (10)	−0.18212 (15)	0.0328 (5)
H23A	−0.4758	0.7966	−0.2481	0.039*
C24	−0.4586 (3)	0.73683 (10)	−0.13934 (16)	0.0324 (5)
H24A	−0.5101	0.7074	−0.1777	0.039*
C25	−0.4041 (3)	0.72607 (9)	−0.04164 (15)	0.0257 (4)
H25A	−0.4157	0.6901	−0.0132	0.031*
C26	−0.3311 (2)	0.77218 (8)	0.01104 (13)	0.0189 (4)
C27	−0.1779 (3)	0.92302 (8)	0.04235 (15)	0.0252 (4)
H27A	−0.1037	0.9338	0.0997	0.038*
H27B	−0.2833	0.9462	0.0380	0.038*
H27C	−0.1146	0.9287	−0.0155	0.038*
C28	−0.0066 (3)	0.97664 (8)	0.74798 (14)	0.0230 (4)
H28A	0.0764	0.9473	0.7696	0.034*
H28B	−0.0956	0.9802	0.7944	0.034*
H28C	0.0549	1.0124	0.7435	0.034*
H1N1	−0.013 (3)	0.8287 (9)	0.4940 (17)	0.023 (6)*
H1N4	−0.033 (3)	0.7535 (12)	0.2352 (19)	0.043 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0302 (3)	0.0151 (2)	0.0296 (2)	0.00422 (19)	−0.00130 (19)	0.00252 (17)
O1	0.0233 (7)	0.0133 (6)	0.0152 (6)	−0.0004 (5)	−0.0006 (5)	−0.0009 (5)
O2	0.0435 (9)	0.0199 (7)	0.0143 (6)	0.0074 (6)	0.0013 (6)	0.0017 (5)
O3	0.0223 (7)	0.0133 (6)	0.0182 (6)	−0.0003 (5)	−0.0025 (5)	−0.0016 (5)
O4	0.0436 (9)	0.0151 (7)	0.0226 (7)	0.0026 (6)	−0.0047 (6)	−0.0031 (5)
N1	0.0245 (8)	0.0101 (7)	0.0135 (7)	0.0008 (6)	−0.0003 (6)	−0.0001 (5)
N2	0.0192 (8)	0.0098 (7)	0.0191 (7)	0.0006 (6)	0.0004 (6)	0.0005 (5)
N3	0.0210 (8)	0.0174 (8)	0.0138 (7)	−0.0005 (6)	−0.0016 (6)	−0.0002 (5)
N4	0.0260 (9)	0.0158 (8)	0.0145 (7)	0.0032 (6)	−0.0027 (6)	−0.0025 (6)
C1	0.0168 (9)	0.0122 (8)	0.0209 (8)	−0.0009 (7)	0.0028 (7)	0.0002 (6)
C2	0.0196 (9)	0.0201 (10)	0.0222 (9)	−0.0016 (7)	0.0005 (7)	0.0025 (7)
C3	0.0198 (10)	0.0225 (10)	0.0289 (10)	0.0013 (8)	0.0005 (8)	0.0067 (8)
C4	0.0219 (10)	0.0138 (9)	0.0375 (11)	0.0032 (7)	0.0059 (8)	0.0039 (8)
C5	0.0197 (9)	0.0147 (9)	0.0293 (10)	−0.0006 (7)	0.0040 (8)	−0.0036 (7)
C6	0.0162 (9)	0.0149 (9)	0.0196 (8)	0.0002 (7)	0.0034 (7)	−0.0011 (6)
C7	0.0188 (9)	0.0143 (9)	0.0182 (8)	−0.0005 (7)	0.0022 (7)	−0.0011 (6)
C8	0.0207 (9)	0.0150 (9)	0.0143 (7)	−0.0012 (7)	0.0002 (7)	−0.0007 (6)
C9	0.0227 (10)	0.0133 (9)	0.0165 (8)	−0.0010 (7)	0.0029 (7)	−0.0017 (6)
C10	0.0161 (9)	0.0128 (8)	0.0169 (8)	−0.0015 (6)	−0.0006 (6)	−0.0005 (6)
C11	0.0147 (9)	0.0135 (8)	0.0188 (8)	−0.0010 (7)	0.0011 (6)	−0.0010 (6)
C12	0.0251 (10)	0.0177 (9)	0.0201 (8)	0.0024 (8)	−0.0033 (7)	−0.0046 (7)
C13	0.0264 (11)	0.0205 (10)	0.0197 (9)	0.0041 (8)	−0.0031 (7)	−0.0011 (7)
C14	0.0195 (9)	0.0132 (9)	0.0258 (9)	0.0008 (7)	0.0021 (7)	0.0018 (7)
C15	0.0301 (11)	0.0136 (9)	0.0257 (9)	0.0020 (8)	−0.0002 (8)	−0.0047 (7)
C16	0.0259 (10)	0.0164 (9)	0.0187 (8)	0.0005 (7)	−0.0022 (7)	−0.0019 (7)
C17	0.0231 (10)	0.0156 (9)	0.0168 (8)	0.0009 (7)	−0.0003 (7)	−0.0026 (6)
C18	0.0218 (9)	0.0151 (9)	0.0171 (8)	−0.0010 (7)	0.0014 (7)	−0.0016 (6)
C19	0.0199 (9)	0.0118 (8)	0.0183 (8)	−0.0003 (7)	−0.0005 (7)	−0.0029 (6)
C20	0.0190 (9)	0.0141 (9)	0.0184 (8)	0.0020 (7)	0.0007 (7)	−0.0009 (6)
C21	0.0198 (9)	0.0192 (10)	0.0172 (8)	0.0038 (7)	0.0005 (7)	−0.0011 (7)
C22	0.0363 (12)	0.0248 (11)	0.0181 (9)	0.0076 (9)	−0.0025 (8)	−0.0002 (7)
C23	0.0401 (13)	0.0350 (13)	0.0217 (9)	0.0093 (10)	−0.0093 (9)	−0.0075 (8)
C24	0.0343 (13)	0.0308 (12)	0.0300 (11)	0.0039 (9)	−0.0110 (9)	−0.0124 (9)
C25	0.0247 (10)	0.0205 (10)	0.0308 (10)	0.0002 (8)	−0.0049 (8)	−0.0062 (8)
C26	0.0171 (9)	0.0202 (9)	0.0187 (8)	0.0022 (7)	−0.0017 (7)	−0.0027 (7)
C27	0.0329 (12)	0.0168 (10)	0.0259 (9)	−0.0006 (8)	0.0031 (8)	0.0012 (7)
C28	0.0298 (11)	0.0191 (10)	0.0196 (8)	0.0000 (8)	−0.0007 (8)	−0.0060 (7)

Geometric parameters (Å, º) top

Cl1—C14	1.7465 (19)	C11—C16	1.394 (2)
O1—C1	1.372 (2)	C11—C12	1.400 (2)
O1—C8	1.387 (2)	C12—C13	1.383 (3)
O2—C9	1.230 (2)	C12—H12A	0.9300
O3—C26	1.370 (2)	C13—C14	1.386 (3)
O3—C19	1.392 (2)	C13—H13A	0.9300
O4—C18	1.217 (2)	C14—C15	1.374 (3)
N1—N2	1.362 (2)	C15—C16	1.394 (3)
N1—C9	1.372 (2)	C15—H15A	0.9300
N1—H1N1	0.89 (2)	C16—H16A	0.9300
N2—C10	1.304 (2)	C17—H17A	0.9300
N3—C17	1.291 (2)	C18—C19	1.476 (2)
N3—N4	1.364 (2)	C19—C20	1.357 (2)
N4—C18	1.372 (2)	C20—C21	1.444 (3)
N4—H1N4	0.95 (3)	C20—C27	1.491 (3)
C1—C2	1.386 (3)	C21—C26	1.395 (3)
C1—C6	1.395 (2)	C21—C22	1.401 (3)
C2—C3	1.387 (3)	C22—C23	1.380 (3)
C2—H2A	0.9300	C22—H22A	0.9300
C3—C4	1.405 (3)	C23—C24	1.406 (3)
C3—H3A	0.9300	C23—H23A	0.9300
C4—C5	1.385 (3)	C24—C25	1.385 (3)
C4—H4A	0.9300	C24—H24A	0.9300
C5—C6	1.403 (3)	C25—C26	1.384 (3)
C5—H5A	0.9300	C25—H25A	0.9300
C6—C7	1.441 (2)	C27—H27A	0.9600
C7—C8	1.361 (2)	C27—H27B	0.9600
C7—C28	1.496 (2)	C27—H27C	0.9600
C8—C9	1.465 (3)	C28—H28A	0.9600
C10—C17	1.463 (2)	C28—H28B	0.9600
C10—C11	1.489 (2)	C28—H28C	0.9600

C1—O1—C8	105.12 (13)	C15—C14—Cl1	120.19 (15)
C26—O3—C19	105.10 (14)	C13—C14—Cl1	118.78 (14)
N2—N1—C9	117.26 (14)	C14—C15—C16	119.41 (17)
N2—N1—H1N1	120.4 (14)	C14—C15—H15A	120.3
C9—N1—H1N1	122.3 (14)	C16—C15—H15A	120.3
C10—N2—N1	119.09 (15)	C15—C16—C11	121.00 (17)
C17—N3—N4	115.35 (15)	C15—C16—H16A	119.5
N3—N4—C18	119.22 (15)	C11—C16—H16A	119.5
N3—N4—H1N4	118.1 (16)	N3—C17—C10	121.18 (16)
C18—N4—H1N4	122.6 (16)	N3—C17—H17A	119.4
O1—C1—C2	125.17 (16)	C10—C17—H17A	119.4
O1—C1—C6	110.60 (15)	O4—C18—N4	124.01 (16)
C2—C1—C6	124.24 (17)	O4—C18—C19	122.89 (17)
C1—C2—C3	115.84 (18)	N4—C18—C19	113.10 (15)
C1—C2—H2A	122.1	C20—C19—O3	112.62 (15)
C3—C2—H2A	122.1	C20—C19—C18	131.24 (17)
C2—C3—C4	121.44 (18)	O3—C19—C18	116.11 (15)
C2—C3—H3A	119.3	C19—C20—C21	105.23 (16)
C4—C3—H3A	119.3	C19—C20—C27	128.68 (17)
C5—C4—C3	121.71 (18)	C21—C20—C27	126.09 (16)
C5—C4—H4A	119.1	C26—C21—C22	119.06 (18)
C3—C4—H4A	119.1	C26—C21—C20	106.37 (15)
C4—C5—C6	117.75 (18)	C22—C21—C20	134.56 (19)
C4—C5—H5A	121.1	C23—C22—C21	118.0 (2)
C6—C5—H5A	121.1	C23—C22—H22A	121.0
C1—C6—C5	119.00 (17)	C21—C22—H22A	121.0
C1—C6—C7	106.45 (16)	C22—C23—C24	121.32 (19)
C5—C6—C7	134.54 (17)	C22—C23—H23A	119.3
C8—C7—C6	105.12 (15)	C24—C23—H23A	119.3
C8—C7—C28	128.27 (17)	C25—C24—C23	121.77 (19)
C6—C7—C28	126.54 (16)	C25—C24—H24A	119.1
C7—C8—O1	112.71 (16)	C23—C24—H24A	119.1
C7—C8—C9	130.51 (16)	C26—C25—C24	115.7 (2)
O1—C8—C9	116.43 (15)	C26—C25—H25A	122.1
O2—C9—N1	123.33 (17)	C24—C25—H25A	122.1
O2—C9—C8	122.71 (16)	O3—C26—C25	125.22 (18)
N1—C9—C8	113.93 (15)	O3—C26—C21	110.68 (16)
N2—C10—C17	126.98 (16)	C25—C26—C21	124.09 (17)
N2—C10—C11	114.60 (15)	C20—C27—H27A	109.5
C17—C10—C11	118.30 (15)	C20—C27—H27B	109.5
C16—C11—C12	117.99 (17)	H27A—C27—H27B	109.5
C16—C11—C10	122.49 (16)	C20—C27—H27C	109.5
C12—C11—C10	119.47 (16)	H27A—C27—H27C	109.5
C13—C12—C11	121.25 (17)	H27B—C27—H27C	109.5
C13—C12—H12A	119.4	C7—C28—H28A	109.5
C11—C12—H12A	119.4	C7—C28—H28B	109.5
C12—C13—C14	119.25 (17)	H28A—C28—H28B	109.5
C12—C13—H13A	120.4	C7—C28—H28C	109.5
C14—C13—H13A	120.4	H28A—C28—H28C	109.5
C15—C14—C13	121.03 (17)	H28B—C28—H28C	109.5

C9—N1—N2—C10	−179.44 (17)	C12—C13—C14—C15	1.5 (3)
C17—N3—N4—C18	−177.48 (17)	C12—C13—C14—Cl1	−178.68 (16)
C8—O1—C1—C2	−179.32 (19)	C13—C14—C15—C16	−1.7 (3)
C8—O1—C1—C6	0.6 (2)	Cl1—C14—C15—C16	178.55 (16)
O1—C1—C2—C3	−179.65 (18)	C14—C15—C16—C11	−0.3 (3)
C6—C1—C2—C3	0.5 (3)	C12—C11—C16—C15	2.4 (3)
C1—C2—C3—C4	0.6 (3)	C10—C11—C16—C15	−175.19 (18)
C2—C3—C4—C5	−0.4 (3)	N4—N3—C17—C10	−174.21 (16)
C3—C4—C5—C6	−0.9 (3)	N2—C10—C17—N3	3.1 (3)
O1—C1—C6—C5	178.29 (16)	C11—C10—C17—N3	178.91 (17)
C2—C1—C6—C5	−1.8 (3)	N3—N4—C18—O4	11.4 (3)
O1—C1—C6—C7	−0.6 (2)	N3—N4—C18—C19	−169.09 (16)
C2—C1—C6—C7	179.31 (18)	C26—O3—C19—C20	−0.2 (2)
C4—C5—C6—C1	2.0 (3)	C26—O3—C19—C18	−178.47 (16)
C4—C5—C6—C7	−179.5 (2)	O4—C18—C19—C20	31.0 (3)
C1—C6—C7—C8	0.4 (2)	N4—C18—C19—C20	−148.4 (2)
C5—C6—C7—C8	−178.3 (2)	O4—C18—C19—O3	−151.14 (19)
C1—C6—C7—C28	177.63 (19)	N4—C18—C19—O3	29.4 (2)
C5—C6—C7—C28	−1.0 (4)	O3—C19—C20—C21	−0.1 (2)
C6—C7—C8—O1	0.0 (2)	C18—C19—C20—C21	177.8 (2)
C28—C7—C8—O1	−177.21 (18)	O3—C19—C20—C27	−179.37 (18)
C6—C7—C8—C9	172.82 (19)	C18—C19—C20—C27	−1.5 (4)
C28—C7—C8—C9	−4.4 (4)	C19—C20—C21—C26	0.4 (2)
C1—O1—C8—C7	−0.4 (2)	C27—C20—C21—C26	179.71 (19)
C1—O1—C8—C9	−174.26 (16)	C19—C20—C21—C22	−178.8 (2)
N2—N1—C9—O2	0.1 (3)	C27—C20—C21—C22	0.5 (4)
N2—N1—C9—C8	178.22 (15)	C26—C21—C22—C23	0.8 (3)
C7—C8—C9—O2	24.7 (3)	C20—C21—C22—C23	180.0 (2)
O1—C8—C9—O2	−162.71 (18)	C21—C22—C23—C24	−0.6 (3)
C7—C8—C9—N1	−153.5 (2)	C22—C23—C24—C25	−0.3 (4)
O1—C8—C9—N1	19.1 (2)	C23—C24—C25—C26	0.9 (3)
N1—N2—C10—C17	−2.9 (3)	C19—O3—C26—C25	179.39 (19)
N1—N2—C10—C11	−178.84 (15)	C19—O3—C26—C21	0.5 (2)
N2—C10—C11—C16	162.87 (18)	C24—C25—C26—O3	−179.46 (19)
C17—C10—C11—C16	−13.4 (3)	C24—C25—C26—C21	−0.8 (3)
N2—C10—C11—C12	−14.7 (3)	C22—C21—C26—O3	178.77 (17)
C17—C10—C11—C12	169.01 (17)	C20—C21—C26—O3	−0.6 (2)
C16—C11—C12—C13	−2.5 (3)	C22—C21—C26—C25	−0.1 (3)
C10—C11—C12—C13	175.12 (18)	C20—C21—C26—C25	−179.49 (19)
C11—C12—C13—C14	0.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···N3	0.89 (2)	1.96 (2)	2.644 (2)	132.3 (18)
N4—H1N4···O2ⁱ	0.95 (3)	2.31 (3)	3.187 (2)	154 (2)
N4—H1N4···N2ⁱ	0.95 (3)	2.48 (3)	3.205 (2)	134 (2)
C17—H17A···O2ⁱ	0.93	2.32	3.165 (2)	150
C28—H28C···O4ⁱⁱ	0.96	2.53	3.464 (2)	164

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

Experimental details

Crystal data
Chemical formula	C₂₈H₂₁ClN₄O₄
M_r	512.94
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.5539 (9), 23.332 (3), 13.6027 (16)
β (°)	94.275 (2)
V (Å³)	2390.8 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.30 × 0.11 × 0.09

Data collection
Diffractometer	Bruker APEX DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.942, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	19379, 6850, 4662
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.701

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.144, 1.03
No. of reflections	6850
No. of parameters	344
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.49

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
N1—H1N1···N3	0.89 (2)	1.96 (2)	2.644 (2)	132.3 (18)
N4—H1N4···O2ⁱ	0.95 (3)	2.31 (3)	3.187 (2)	154 (2)
N4—H1N4···N2ⁱ	0.95 (3)	2.48 (3)	3.205 (2)	134 (2)
C17—H17A···O2ⁱ	0.93	2.32	3.165 (2)	150
C28—H28C···O4ⁱⁱ	0.96	2.53	3.464 (2)	164

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and TSC thank Universiti Sains Malaysia (USM) for a Research University Grant (No. 1001/PFIZIK/811160). TSC thanks the Malaysian government and USM for the award of a Research Fellowship. The authors thank the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University, for funding and facilities.

References

Abdel-Aziz, H. A. & Mekawey, A. A. I. (2009). Eur. J. Med. Chem. 44, 4985–4997. Web of Science PubMed CAS Google Scholar
Abdel-Aziz, H. A., Mekawey, A. A. I. & Dawood, K. M. (2009). Eur. J. Med. Chem. 44, 3637–3644. Web of Science PubMed CAS Google Scholar
Abdel-Wahab, B. F., Abdel-Aziz, H. A. & Ahmed, E. M. (2009). Monatsh. Chem. 140, 601–605. CAS Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bhovi, V. K., Bodke, Y. D., Biradar, S., Swamy, B. E. K. & Umesh, S. (2010). Phosphorus Sulfur Silicon Relat. Elem. 185, 110–116. Web of Science CrossRef CAS Google Scholar
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Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals 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

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Volume 68| Part 8| August 2012| Pages o2405-o2406

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

(N′,N′′Z,N′,N′′E)-N′,N′′-[1-(4-Chloro­phen­yl)ethane-1,2-diyl­­idene]bis­­(3-methyl-1-benzo­furan-2-carbohydrazide)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

(N′,N′′Z,N′,N′′E)-N′,N′′-[1-(4-Chlorophenyl)ethane-1,2-diylidene]bis(3-methyl-1-benzofuran-2-carbohydrazide)