(4-Chloro­phen­yl)[1-(4-methoxy­phen­yl)-3-(5-nitro-2-fur­yl)-1H-pyrazol-4-yl]methanone

Goh, J.H.; Fun, H.-K.; Nithinchandra; Kalluraya, B.; Rai, N.S.

doi:10.1107/S1600536810011931

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Pages o1063-o1064

https://doi.org/10.1107/S1600536810011931

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(4-Chlorophenyl)[1-(4-methoxyphenyl)-3-(5-nitro-2-furyl)-1H-pyrazol-4-yl]methanone

Jia Hao Goh,^a ‡ Hoong-Kun Fun,^a ^*§ Nithinchandra,^b B. Kalluraya ^b and N. Satheesh Rai ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 30 March 2010; accepted 30 March 2010; online 14 April 2010)

In the title compound, C₂₁H₁₄ClN₃O₅, an intramolecular C—H⋯O hydrogen bond generates an S(7) ring motif and the furan and pyrazole rings are almost coplanar, making a dihedral angle of 1.98 (5)°. The pyrazole ring is inclined at dihedral angles of 47.59 (4) and 7.27 (4)° to the chlorophenyl and methoxyphenyl groups, respectively. The nitro group is almost coplanar to its attached furan ring [dihedral angle = 2.03 (12)°]. In the crystal, intermolecular C—H⋯O hydrogen bonds link the molecules into a three-dimensional network. The crystal structure also features short intermolecular O⋯N [2.8546 (12) Å] and Cl⋯O [3.0844 (9) Å] contacts as well as aromatic π–π stacking interactions [centroid–centroid distance = 3.4367 (6) Å].

Related literature

For general background to and applications of the title compound, see: Hedge et al. (2006 ); Kalluraya et al. (1994 ); Rai & Kalluraya (2006 ); Rai et al. (2008 ). For graph-set theory, see: Bernstein et al. (1995 ). For closely related structures, see: Goh et al. (2009a ,b , 2010 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₁H₁₄ClN₃O₅
M_r = 423.80
Triclinic, $[P \overline 1]$
a = 9.5589 (8) Å
b = 9.6603 (8) Å
c = 10.6401 (9) Å
α = 95.523 (2)°
β = 91.074 (2)°
γ = 107.706 (2)°
V = 930.44 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 100 K
0.35 × 0.30 × 0.15 mm

Data collection

Bruker SMART APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.919, T_max = 0.963
31674 measured reflections
8076 independent reflections
7107 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.146
S = 1.13
8076 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.87 e Å⁻³
Δρ_min = −0.70 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O2	0.93	2.27	2.9153 (12)	126
C2—H2A⋯O5ⁱ	0.93	2.48	3.2820 (13)	145
C14—H14A⋯O4ⁱⁱ	0.93	2.46	3.3846 (12)	175
C21—H21A⋯O2ⁱⁱⁱ	0.96	2.55	3.5064 (14)	173
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x+1, y+1, z; (iii) x+1, y, 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/S1600536810011931/hb5382sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810011931/hb5382Isup2.hkl

checkCIF report

Comment top

The pyrazole nucleus constitutes an interesting class of organic compound with diverse chemical applications. They possess anti-pyretic, anti-tumor, tranquilizing and herbicidal activities. Sydnones are easily accessible aromatic compounds and versatile synthetic intermediates with a masked azomethine imine unit. The 1,3-dipolar cycloaddition reaction with various dipolarophiles offers a convenient synthetic route for the preparation of pyrazole derivatives and has been studied extensively (Rai & Kalluraya, 2006; Rai et al., 2008). The incorporation of 5-nitrofuran moiety into various heterocyclic systems has found to increase their biological activities. We have reported a few heterocyclic systems carrying 5-nitrofuran moiety as potent anti-microbial agents (Hedge et al., 2006). In continuation of our studies on 1,3-dipolar cycloaddition reactions of sydnones with dipolarphiles carrying nitrofuran moiety (Kalluraya et al., 1994), we herein report the crystal structure of the above pyrazole compound.

In the title pyrazole compound, an intramolecular C11—H11A···O2 hydrogen bond (Table 1) generates a seven-membered ring, producing an S(7) ring motif (Fig. 1, Bernstein et al., 1995). The furan (C10-C13/O1) and pyrazole (C8/C9/N2/N1/C14) rings are essentially planar, with maximum deviations of 0.003 (1) and 0.004 (1) Å, respectively, at atoms O1 and N2. These two rings are coplanar to one another, making a dihedral angle of 3.06 (10)° between them. The pyrazole ring is inclined at dihedral angles of 47.59 (4) and 7.27 (4)°, respectively, with the mean planes through 4-chlorophenyl (C1-C6/Cl1) and 4-methoxyphenyl (C15-C20/O3/C21) groups. The nitro group is coplanar with the attached furan ring, as indicated by the dihedral angle formed of 2.03 (12)°. The bond lengths and angles are comparable to those observed in closely related pyrazole structures (Goh et al., 2009a,b, 2010).

In the crystal structure, intermolecular C2—H2A···O5, C14—H14A···O4 and C21—H21A···O2 hydrogen bonds (Table 1) link neighbouring molecules into a three-dimensional extended network. The interesting feature of the crystal structure is the short intermolecular Cl1···O3 [3.0844 (9) Å, symmetry code: -x+3, -y+2, -z+1] and O2···N3 [2.8546 (12) Å, symmetry code: -x+1, -y+1, -z+1] interactions which are shorter than the sum of the van der Waals radii of the relevant atoms. The crystal structure is further stabilized by the weak intermolecular π–π interactions involving the pyrazole ring [Cg1···Cg1 = 3.4367 (6) Å; symmetry code: -x+2, -y+1, -z+1].

Related literature top

For general background to and applications of the title compound, see: Hedge et al. (2006); Kalluraya et al. (1994); Rai & Kalluraya (2006); Rai et al. (2008). For graph-set theory, see: Bernstein et al. (1995). For closely related structures, see: Goh et al. (2009a,b, 2010). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

3-(p-Anisyl)sydnone (0.01 mol) and 1-(p-chlorophenyl)-3-(5-nitro-2-furyl)-2-propyn-1-one (0.01 mol) were dissolved in dry xylene (10 ml) and refluxed for 4 h. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The crude product obtained was purified by recrystallization from a mixture of ethanol and DMF. The solid obtained was collected by filtration, washed with ethanol and dried. Orange blocks of (I) were obtained from a 1:2 mixture of ethanol and DMF by slow evaporation.

Structure description top

For general background to and applications of the title compound, see: Hedge et al. (2006); Kalluraya et al. (1994); Rai & Kalluraya (2006); Rai et al. (2008). For graph-set theory, see: Bernstein et al. (1995). For closely related structures, see: Goh et al. (2009a,b, 2010). 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 (I), showing 50% probability displacement ellipsoids for non-H atoms. An intramolecular hydrogen bond is shown as dashed line.
	Fig. 2. The crystal structure of (I), viewed along the c axis, showing the three-dimensional extended network. Hydrogen atoms not involved in intermolecular interactions (dashed lines) have been omitted for clarity.

(4-Chlorophenyl)[1-(4-methoxyphenyl)-3-(5-nitro-2-furyl)-1H- pyrazol-4-yl]methanone top

Crystal data top

C₂₁H₁₄ClN₃O₅	Z = 2
M_r = 423.80	F(000) = 436
Triclinic, P1	D_x = 1.513 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5589 (8) Å	Cell parameters from 9944 reflections
b = 9.6603 (8) Å	θ = 2.6–37.6°
c = 10.6401 (9) Å	µ = 0.25 mm⁻¹
α = 95.523 (2)°	T = 100 K
β = 91.074 (2)°	Block, orange
γ = 107.706 (2)°	0.35 × 0.30 × 0.15 mm
V = 930.44 (13) Å³

Data collection top

Bruker SMART APEX DUO CCD diffractometer	8076 independent reflections
Radiation source: fine-focus sealed tube	7107 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
φ and ω scans	θ_max = 35.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
T_min = 0.919, T_max = 0.963	k = −13→15
31674 measured reflections	l = −17→17

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.095P)² + 0.1254P] where P = (F_o² + 2F_c²)/3
8076 reflections	(Δ/σ)_max = 0.001
272 parameters	Δρ_max = 0.87 e Å⁻³
0 restraints	Δρ_min = −0.70 e Å⁻³

Crystal data top

C₂₁H₁₄ClN₃O₅	γ = 107.706 (2)°
M_r = 423.80	V = 930.44 (13) Å³
Triclinic, P1	Z = 2
a = 9.5589 (8) Å	Mo Kα radiation
b = 9.6603 (8) Å	µ = 0.25 mm⁻¹
c = 10.6401 (9) Å	T = 100 K
α = 95.523 (2)°	0.35 × 0.30 × 0.15 mm
β = 91.074 (2)°

Data collection top

Bruker SMART APEX DUO CCD diffractometer	8076 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	7107 reflections with I > 2σ(I)
T_min = 0.919, T_max = 0.963	R_int = 0.026
31674 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.13	Δρ_max = 0.87 e Å⁻³
8076 reflections	Δρ_min = −0.70 e Å⁻³
272 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 esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	1.29464 (2)	1.14454 (3)	0.06814 (2)	0.02139 (7)
O1	0.61940 (7)	0.32154 (7)	0.56102 (7)	0.01521 (12)
O2	0.71984 (7)	0.69219 (8)	0.30892 (7)	0.01788 (13)
O3	1.40488 (8)	0.71448 (9)	1.04135 (7)	0.02060 (14)
O4	0.30019 (9)	0.02849 (9)	0.52238 (8)	0.02777 (17)
O5	0.47299 (9)	0.09317 (9)	0.67232 (9)	0.02794 (18)
N1	0.99713 (8)	0.64428 (8)	0.64105 (7)	0.01227 (12)
N2	0.87287 (8)	0.52812 (8)	0.62820 (7)	0.01314 (12)
N3	0.41817 (9)	0.10960 (9)	0.57182 (8)	0.01796 (14)
C1	1.11008 (9)	0.82550 (10)	0.28130 (8)	0.01484 (14)
H1A	1.1386	0.7582	0.3241	0.018*
C2	1.21148 (9)	0.92103 (10)	0.21216 (9)	0.01643 (15)
H2A	1.3069	0.9161	0.2064	0.020*
C3	1.16768 (9)	1.02368 (10)	0.15196 (8)	0.01521 (14)
C4	1.02482 (10)	1.03149 (10)	0.15658 (9)	0.01617 (15)
H4A	0.9977	1.1017	0.1167	0.019*
C5	0.92349 (9)	0.93211 (10)	0.22196 (8)	0.01508 (14)
H5A	0.8266	0.9332	0.2228	0.018*
C6	0.96547 (9)	0.83057 (9)	0.28646 (8)	0.01292 (13)
C7	0.84764 (9)	0.72576 (9)	0.35099 (8)	0.01295 (13)
C8	0.88513 (9)	0.66693 (9)	0.46450 (8)	0.01251 (13)
C9	0.80310 (8)	0.54115 (9)	0.52175 (8)	0.01230 (13)
C10	0.66580 (9)	0.42891 (9)	0.48123 (8)	0.01289 (13)
C11	0.56829 (10)	0.40179 (10)	0.37915 (8)	0.01690 (15)
H11A	0.5753	0.4580	0.3119	0.020*
C12	0.45459 (10)	0.27164 (11)	0.39557 (9)	0.01852 (16)
H12A	0.3722	0.2250	0.3421	0.022*
C13	0.49222 (9)	0.23009 (9)	0.50622 (9)	0.01568 (15)
C14	1.00849 (9)	0.72922 (9)	0.54574 (8)	0.01321 (14)
H14A	1.0848	0.8137	0.5363	0.016*
C15	1.09929 (9)	0.66115 (9)	0.74528 (8)	0.01229 (13)
C16	1.07607 (9)	0.55323 (10)	0.82671 (8)	0.01586 (15)
H16A	0.9930	0.4716	0.8143	0.019*
C17	1.17703 (10)	0.56696 (11)	0.92700 (9)	0.01755 (15)
H17A	1.1624	0.4936	0.9805	0.021*
C18	1.29982 (9)	0.69077 (10)	0.94696 (8)	0.01540 (14)
C19	1.32113 (9)	0.80016 (10)	0.86573 (9)	0.01607 (15)
H19A	1.4019	0.8839	0.8800	0.019*
C20	1.22302 (9)	0.78476 (9)	0.76433 (8)	0.01446 (14)
H20A	1.2393	0.8564	0.7091	0.017*
C21	1.39244 (12)	0.60104 (13)	1.12158 (10)	0.0247 (2)
H21A	1.4770	0.6276	1.1793	0.037*
H21B	1.3867	0.5115	1.0709	0.037*
H21C	1.3053	0.5879	1.1684	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.01544 (10)	0.02511 (12)	0.01991 (12)	−0.00141 (8)	0.00097 (7)	0.00950 (8)
O1	0.0108 (2)	0.0127 (3)	0.0197 (3)	−0.0006 (2)	0.0000 (2)	0.0044 (2)
O2	0.0113 (2)	0.0195 (3)	0.0219 (3)	0.0026 (2)	−0.0025 (2)	0.0051 (2)
O3	0.0142 (3)	0.0274 (4)	0.0167 (3)	0.0004 (3)	−0.0036 (2)	0.0065 (3)
O4	0.0233 (3)	0.0221 (3)	0.0248 (4)	−0.0114 (3)	0.0003 (3)	−0.0004 (3)
O5	0.0186 (3)	0.0246 (4)	0.0393 (5)	0.0009 (3)	−0.0044 (3)	0.0172 (3)
N1	0.0098 (3)	0.0114 (3)	0.0141 (3)	0.0005 (2)	−0.0005 (2)	0.0027 (2)
N2	0.0099 (3)	0.0119 (3)	0.0157 (3)	0.0003 (2)	−0.0003 (2)	0.0025 (2)
N3	0.0147 (3)	0.0128 (3)	0.0234 (4)	−0.0004 (2)	0.0030 (3)	0.0023 (3)
C1	0.0117 (3)	0.0165 (3)	0.0162 (3)	0.0037 (3)	−0.0007 (2)	0.0037 (3)
C2	0.0111 (3)	0.0196 (4)	0.0177 (4)	0.0027 (3)	−0.0002 (3)	0.0045 (3)
C3	0.0131 (3)	0.0165 (3)	0.0140 (3)	0.0010 (3)	0.0003 (2)	0.0034 (3)
C4	0.0156 (3)	0.0177 (4)	0.0161 (3)	0.0053 (3)	0.0015 (3)	0.0055 (3)
C5	0.0134 (3)	0.0173 (3)	0.0159 (3)	0.0057 (3)	0.0018 (2)	0.0049 (3)
C6	0.0114 (3)	0.0133 (3)	0.0137 (3)	0.0027 (2)	0.0002 (2)	0.0028 (2)
C7	0.0109 (3)	0.0130 (3)	0.0146 (3)	0.0028 (2)	−0.0001 (2)	0.0026 (2)
C8	0.0102 (3)	0.0123 (3)	0.0140 (3)	0.0017 (2)	−0.0001 (2)	0.0025 (2)
C9	0.0098 (3)	0.0115 (3)	0.0150 (3)	0.0021 (2)	0.0008 (2)	0.0020 (2)
C10	0.0100 (3)	0.0121 (3)	0.0150 (3)	0.0010 (2)	0.0014 (2)	0.0016 (2)
C11	0.0153 (3)	0.0168 (4)	0.0143 (3)	−0.0012 (3)	−0.0006 (3)	0.0011 (3)
C12	0.0159 (3)	0.0183 (4)	0.0154 (4)	−0.0027 (3)	−0.0003 (3)	−0.0009 (3)
C13	0.0123 (3)	0.0127 (3)	0.0185 (4)	−0.0012 (3)	0.0018 (3)	0.0008 (3)
C14	0.0112 (3)	0.0125 (3)	0.0146 (3)	0.0011 (2)	−0.0002 (2)	0.0030 (2)
C15	0.0101 (3)	0.0124 (3)	0.0134 (3)	0.0019 (2)	0.0001 (2)	0.0017 (2)
C16	0.0140 (3)	0.0154 (3)	0.0151 (3)	−0.0008 (3)	−0.0009 (3)	0.0042 (3)
C17	0.0152 (3)	0.0198 (4)	0.0153 (4)	0.0008 (3)	−0.0007 (3)	0.0061 (3)
C18	0.0117 (3)	0.0197 (4)	0.0133 (3)	0.0027 (3)	−0.0002 (2)	0.0021 (3)
C19	0.0116 (3)	0.0159 (3)	0.0186 (4)	0.0011 (3)	−0.0013 (3)	0.0021 (3)
C20	0.0112 (3)	0.0130 (3)	0.0180 (4)	0.0016 (2)	−0.0011 (2)	0.0031 (3)
C21	0.0208 (4)	0.0327 (5)	0.0192 (4)	0.0042 (4)	−0.0033 (3)	0.0096 (4)

Geometric parameters (Å, º) top

Cl1—C3	1.7351 (9)	C7—C8	1.4662 (12)
O1—C13	1.3488 (11)	C8—C14	1.3892 (11)
O1—C10	1.3774 (10)	C8—C9	1.4294 (11)
O2—C7	1.2282 (10)	C9—C10	1.4516 (11)
O3—C18	1.3593 (11)	C10—C11	1.3696 (12)
O3—C21	1.4313 (13)	C11—C12	1.4180 (13)
O4—N3	1.2343 (11)	C11—H11A	0.9300
O5—N3	1.2270 (12)	C12—C13	1.3563 (13)
N1—C14	1.3503 (11)	C12—H12A	0.9300
N1—N2	1.3574 (10)	C14—H14A	0.9300
N1—C15	1.4275 (11)	C15—C16	1.3883 (12)
N2—C9	1.3393 (11)	C15—C20	1.3969 (12)
N3—C13	1.4200 (12)	C16—C17	1.3942 (12)
C1—C2	1.3949 (12)	C16—H16A	0.9300
C1—C6	1.3998 (12)	C17—C18	1.3933 (13)
C1—H1A	0.9300	C17—H17A	0.9300
C2—C3	1.3906 (12)	C18—C19	1.3987 (13)
C2—H2A	0.9300	C19—C20	1.3828 (12)
C3—C4	1.3919 (12)	C19—H19A	0.9300
C4—C5	1.3899 (13)	C20—H20A	0.9300
C4—H4A	0.9300	C21—H21A	0.9600
C5—C6	1.3975 (12)	C21—H21B	0.9600
C5—H5A	0.9300	C21—H21C	0.9600
C6—C7	1.4948 (12)

C13—O1—C10	105.18 (7)	O1—C10—C9	114.95 (7)
C18—O3—C21	117.66 (8)	C10—C11—C12	106.87 (8)
C14—N1—N2	112.41 (7)	C10—C11—H11A	126.6
C14—N1—C15	128.09 (7)	C12—C11—H11A	126.6
N2—N1—C15	119.46 (7)	C13—C12—C11	104.95 (8)
C9—N2—N1	105.18 (7)	C13—C12—H12A	127.5
O5—N3—O4	124.52 (9)	C11—C12—H12A	127.5
O5—N3—C13	119.17 (8)	O1—C13—C12	112.92 (8)
O4—N3—C13	116.31 (9)	O1—C13—N3	116.80 (8)
C2—C1—C6	120.23 (8)	C12—C13—N3	130.27 (8)
C2—C1—H1A	119.9	N1—C14—C8	107.30 (7)
C6—C1—H1A	119.9	N1—C14—H14A	126.3
C3—C2—C1	118.94 (8)	C8—C14—H14A	126.3
C3—C2—H2A	120.5	C16—C15—C20	120.14 (8)
C1—C2—H2A	120.5	C16—C15—N1	119.68 (7)
C2—C3—C4	121.82 (8)	C20—C15—N1	120.17 (7)
C2—C3—Cl1	118.96 (7)	C15—C16—C17	120.14 (8)
C4—C3—Cl1	119.22 (7)	C15—C16—H16A	119.9
C5—C4—C3	118.60 (8)	C17—C16—H16A	119.9
C5—C4—H4A	120.7	C18—C17—C16	119.84 (8)
C3—C4—H4A	120.7	C18—C17—H17A	120.1
C4—C5—C6	120.81 (8)	C16—C17—H17A	120.1
C4—C5—H5A	119.6	O3—C18—C17	124.49 (8)
C6—C5—H5A	119.6	O3—C18—C19	115.85 (8)
C5—C6—C1	119.53 (8)	C17—C18—C19	119.66 (8)
C5—C6—C7	116.77 (7)	C20—C19—C18	120.48 (8)
C1—C6—C7	123.58 (7)	C20—C19—H19A	119.8
O2—C7—C8	120.95 (8)	C18—C19—H19A	119.8
O2—C7—C6	119.13 (8)	C19—C20—C15	119.70 (8)
C8—C7—C6	119.91 (7)	C19—C20—H20A	120.1
C14—C8—C9	104.13 (7)	C15—C20—H20A	120.1
C14—C8—C7	126.36 (8)	O3—C21—H21A	109.5
C9—C8—C7	129.40 (7)	O3—C21—H21B	109.5
N2—C9—C8	110.98 (7)	H21A—C21—H21B	109.5
N2—C9—C10	117.95 (7)	O3—C21—H21C	109.5
C8—C9—C10	131.03 (8)	H21A—C21—H21C	109.5
C11—C10—O1	110.07 (7)	H21B—C21—H21C	109.5
C11—C10—C9	134.98 (8)

C14—N1—N2—C9	−0.53 (9)	O1—C10—C11—C12	0.31 (10)
C15—N1—N2—C9	−178.56 (7)	C9—C10—C11—C12	179.62 (9)
C6—C1—C2—C3	1.91 (13)	C10—C11—C12—C13	−0.05 (10)
C1—C2—C3—C4	−1.44 (14)	C10—O1—C13—C12	0.43 (10)
C1—C2—C3—Cl1	178.93 (7)	C10—O1—C13—N3	−178.49 (7)
C2—C3—C4—C5	−0.89 (14)	C11—C12—C13—O1	−0.24 (11)
Cl1—C3—C4—C5	178.74 (7)	C11—C12—C13—N3	178.50 (9)
C3—C4—C5—C6	2.78 (14)	O5—N3—C13—O1	−1.02 (13)
C4—C5—C6—C1	−2.31 (13)	O4—N3—C13—O1	178.36 (8)
C4—C5—C6—C7	−178.41 (8)	O5—N3—C13—C12	−179.72 (10)
C2—C1—C6—C5	−0.08 (13)	O4—N3—C13—C12	−0.34 (15)
C2—C1—C6—C7	175.74 (8)	N2—N1—C14—C8	0.08 (9)
C5—C6—C7—O2	27.96 (12)	C15—N1—C14—C8	177.90 (7)
C1—C6—C7—O2	−147.96 (9)	C9—C8—C14—N1	0.37 (9)
C5—C6—C7—C8	−150.78 (8)	C7—C8—C14—N1	177.02 (8)
C1—C6—C7—C8	33.30 (12)	C14—N1—C15—C16	−172.85 (8)
O2—C7—C8—C14	−156.41 (9)	N2—N1—C15—C16	4.84 (12)
C6—C7—C8—C14	22.30 (12)	C14—N1—C15—C20	6.33 (13)
O2—C7—C8—C9	19.38 (14)	N2—N1—C15—C20	−175.98 (7)
C6—C7—C8—C9	−161.90 (8)	C20—C15—C16—C17	−0.74 (13)
N1—N2—C9—C8	0.76 (9)	N1—C15—C16—C17	178.45 (8)
N1—N2—C9—C10	178.64 (7)	C15—C16—C17—C18	1.34 (14)
C14—C8—C9—N2	−0.72 (9)	C21—O3—C18—C17	3.45 (14)
C7—C8—C9—N2	−177.23 (8)	C21—O3—C18—C19	−176.00 (9)
C14—C8—C9—C10	−178.24 (8)	C16—C17—C18—O3	−179.70 (8)
C7—C8—C9—C10	5.26 (15)	C16—C17—C18—C19	−0.27 (14)
C13—O1—C10—C11	−0.45 (9)	O3—C18—C19—C20	178.05 (8)
C13—O1—C10—C9	−179.91 (7)	C17—C18—C19—C20	−1.43 (13)
N2—C9—C10—C11	−177.28 (9)	C18—C19—C20—C15	2.03 (13)
C8—C9—C10—C11	0.10 (16)	C16—C15—C20—C19	−0.95 (13)
N2—C9—C10—O1	2.01 (11)	N1—C15—C20—C19	179.87 (8)
C8—C9—C10—O1	179.38 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O2	0.93	2.27	2.9153 (12)	126
C2—H2A···O5ⁱ	0.93	2.48	3.2820 (13)	145
C14—H14A···O4ⁱⁱ	0.93	2.46	3.3846 (12)	175
C21—H21A···O2ⁱⁱⁱ	0.96	2.55	3.5064 (14)	173

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₄ClN₃O₅
M_r	423.80
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.5589 (8), 9.6603 (8), 10.6401 (9)
α, β, γ (°)	95.523 (2), 91.074 (2), 107.706 (2)
V (Å³)	930.44 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.35 × 0.30 × 0.15

Data collection
Diffractometer	Bruker SMART APEX DUO CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.919, 0.963
No. of measured, independent and observed [I > 2σ(I)] reflections	31674, 8076, 7107
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.807

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.146, 1.13
No. of reflections	8076
No. of parameters	272
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.87, −0.70

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
C11—H11A···O2	0.93	2.27	2.9153 (12)	126
C2—H2A···O5ⁱ	0.93	2.48	3.2820 (13)	145
C14—H14A···O4ⁱⁱ	0.93	2.46	3.3846 (12)	175
C21—H21A···O2ⁱⁱⁱ	0.96	2.55	3.5064 (14)	173

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

Footnotes

‡Thomson Reuters ResearcherID: C-7576-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship.

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