N-(2,5-Dichloro­phen­yl)maleamic acid

Shakuntala, K.; Gowda, B.T.; Tokarčík, M.; Kožíšek, J.

doi:10.1107/S1600536809048715

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3119

doi:10.1107/S1600536809048715

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N-(2,5-Dichlorophenyl)maleamic acid

K. Shakuntala,^a B. Thimme Gowda,^a ^* Miroslav Tokarčík ^b and Jozef Kožíšek ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bFaculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 13 November 2009; accepted 16 November 2009; online 18 November 2009)

The asymmetric unit of the title compound, C₁₀H₇Cl₂NO₃, contains two independent molecules. The molecular conformation of each maleamic unit is stabilized by an intramolecular O—H⋯O_carbonyl hydrogen bond owing to the anti disposition of the participating entities. The mean planes through the benzene ring and the amido group are inclined at angles of 45.7 (1) and 40.8 (1)° in the two molecules. In the crystal, the independent molecules self-associate via N—H⋯O hydrogen bonds into zigzag ribbons propagating along the a axis. The ribbons are weakly coupled by C—H⋯π and C—H⋯O interactions.

Related literature

For related structures, see: Gowda, Foro et al. (2009 ); Gowda, Tokarčík et al. (2009a ,b ); Leiserowitz (1976 ); Lo & Ng (2009 ); Prasad et al. (2002 ).

Experimental

Crystal data

C₁₀H₇Cl₂NO₃
M_r = 260.07
Orthorhombic, P b c a
a = 13.1618 (2) Å
b = 14.6993 (2) Å
c = 22.8406 (3) Å
V = 4418.95 (11) Å³
Z = 16
Mo Kα radiation
μ = 0.58 mm⁻¹
T = 295 K
0.40 × 0.33 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: analytical (CrysAlis Pro ; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.836, T_max = 0.892
61823 measured reflections
4191 independent reflections
3514 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.079
S = 1.08
4191 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3ⁱ	0.86	2.07	2.8938 (17)	160
N2—H2N⋯O6ⁱⁱ	0.86	2.09	2.9263 (17)	164
O2—H2A⋯O1	0.82	1.68	2.4979 (15)	175
O5—H5A⋯O4	0.82	1.68	2.4846 (15)	166
C7—H7⋯Cg2	0.93	2.77	3.6745 (15)	163
C18—H18⋯O5ⁱⁱⁱ	0.93	2.58	3.4186 (19)	151
Symmetry codes: (i) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ . Cg2 is the centroid of the C15–C20 ring.

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis Pro ; data reduction: CrysAlis Pro ; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2002 ); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ) and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809048715/tk2578sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809048715/tk2578Isup2.hkl

checkCIF report

Comment top

As a part of studying the effect of ring- and side-chain substitutions on the crystal structures of biologically significant amides (Gowda, Foro et al., 2009; Gowda, Tokarčík et al., 2009a,b; Prasad et al., 2002), the crystal structure of N-(2,5-dichlorophenyl)-maleamic acid (I) has been determined. The asymmetric unit of (I) contains two independent molecules (Fig. 1). The conformations of the N—H and C=O bonds in the amide segment of the structure are anti to each other, and those of the amide-O atom and the carbonyl-O atom of the acid segment are also anti to each other. The anti conformation of the C=O and O—H bonds of the acid group is comparatively rare and has been observed previously in N-phenylmaleamic acid (Lo & Ng, 2009), N-(2,6-dimethylphenyl)maleamic acid (Gowda, Tokarčík et al., 2009a), and N-(3,4-dimethylphenyl)maleamic acid (Gowda, Tokarčík et al., 2009b). The various modes of interlinking carboxylic acids by hydrogen bonds is described elsewhere (Leiserowitz, 1976). Each maleamic moiety includes a short intramolecular hydrogen O–H···O bond (Table 1). The mean planes through the phenyl ring and the amido group –NHCO– form dihedral angles of 45.7 (1) and 40.8 (1) ° in the first and second molecules, respectively. All non-hydrogen atoms of the maleamic moiety in the first molecule fit very well to a plane, having the r.m.s. deviation of fitted atoms 0.013 Å. The mean plane through the maleamic moiety in the second molecule has a r.m.s. deviation of 0.098 Å. In the crystal structure, intermolecular N–H···O hydrogen bonds link self-associated molecules into two distinct zig-zag ribbons propagating in the [1 0 0] direction (Fig. 2). These ribbons are weakly coupled by a C—H···π interaction, with atom C7-H acting as the donor and the aryl ring C15—C20 as the acceptor. The centroid of the C15—C20 ring is denoted Cg2 in the Table 1.

Related literature top

For related structures, see: Gowda, Foro et al. (2009); Gowda, Tokarčík et al. (2009a,b); Leiserowitz (1976); Lo & Ng (2009); Prasad et al. (2002). Cg2 is the centroid of the C15–C20 ring.

Experimental top

A solution of maleic anhydride (0.025 mol) in toluene (25 ml) was treated drop-wise with a solution of 2,5-dichloroaniline (0.025 mol) also in toluene (20 ml) with constant stirring. The resulting mixture was warmed with stirring for 30 min and set aside for an additional 30 min at room temperature for completion of the reaction. The mixture was then treated with dilute hydrochloric acid to remove the unreacted 2,5-dichloroaniline. The resultant solid N-(2,5-dichlorophenyl)maleamic acid was filtered under suction and washed thoroughly with water to remove the unreacted maleic anhydride and maleic acid. It was recrystallized to constant melting point from ethanol. Colourless crystals were grown by slow evaporation (room temperature) of an ethanol solution of (I).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of (I) showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Part of crystal structure of (I) showing 1-D zig-zag supramolecular chains generated by N—H···O hydrogen bonds (dashed lines). Symmetry codes (i) x - 1/2,y,-z + 1/2; (ii) x - 1/2,y,-z + 3/2.

N-(2,5-Dichlorophenyl)maleamic acid top

Crystal data top

C₁₀H₇Cl₂NO₃	F(000) = 2112
M_r = 260.07	D_x = 1.564 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 31107 reflections
a = 13.1618 (2) Å	θ = 1.6–29.5°
b = 14.6993 (2) Å	µ = 0.58 mm⁻¹
c = 22.8406 (3) Å	T = 295 K
V = 4418.95 (11) Å³	Block, colourless
Z = 16	0.40 × 0.33 × 0.24 mm

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	4191 independent reflections
Graphite monochromator	3514 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm^-1	R_int = 0.029
ω scans	θ_max = 25.7°, θ_min = 2.3°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	h = −16→16
T_min = 0.836, T_max = 0.892	k = −17→17
61823 measured reflections	l = −27→27

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0445P)² + 0.705P] where P = (F_o² + 2F_c²)/3
4191 reflections	(Δ/σ)_max = 0.001
289 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₀H₇Cl₂NO₃	V = 4418.95 (11) Å³
M_r = 260.07	Z = 16
Orthorhombic, Pbca	Mo Kα radiation
a = 13.1618 (2) Å	µ = 0.58 mm⁻¹
b = 14.6993 (2) Å	T = 295 K
c = 22.8406 (3) Å	0.40 × 0.33 × 0.24 mm

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	4191 independent reflections
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	3514 reflections with I > 2σ(I)
T_min = 0.836, T_max = 0.892	R_int = 0.029
61823 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.079	H-atom parameters constrained
S = 1.08	Δρ_max = 0.22 e Å⁻³
4191 reflections	Δρ_min = −0.25 e Å⁻³
289 parameters

Special details top

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
C1	0.73471 (10)	−0.00911 (10)	0.32684 (6)	0.0350 (3)
C2	0.72297 (11)	−0.04413 (10)	0.26641 (7)	0.0415 (3)
H2	0.6567	−0.0563	0.2547	0.05*
C3	0.79490 (12)	−0.06048 (11)	0.22658 (7)	0.0441 (4)
H3	0.7699	−0.0823	0.1912	0.053*
C4	0.90735 (12)	−0.05043 (11)	0.22796 (7)	0.0441 (4)
C5	0.63841 (10)	0.02870 (9)	0.41515 (6)	0.0339 (3)
C6	0.56221 (11)	0.08972 (9)	0.43094 (6)	0.0364 (3)
C7	0.54753 (12)	0.11305 (10)	0.48908 (7)	0.0415 (3)
H7	0.4961	0.1535	0.4992	0.05*
C8	0.60896 (11)	0.07648 (10)	0.53206 (7)	0.0416 (3)
H8	0.5994	0.0918	0.5712	0.05*
C9	0.68479 (11)	0.01675 (10)	0.51585 (6)	0.0374 (3)
C10	0.70068 (11)	−0.00722 (10)	0.45830 (6)	0.0363 (3)
H10	0.7527	−0.0472	0.4485	0.044*
N1	0.64725 (9)	0.00060 (8)	0.35603 (5)	0.0376 (3)
H1N	0.592	−0.0112	0.3374	0.045*
O1	0.81770 (8)	0.01020 (8)	0.34893 (4)	0.0466 (3)
O2	0.95290 (9)	−0.01830 (9)	0.27441 (5)	0.0616 (3)
H2A	0.9105	−0.0062	0.2995	0.092*
O3	0.95614 (9)	−0.07270 (9)	0.18517 (5)	0.0602 (3)
Cl1	0.48365 (3)	0.13629 (3)	0.378143 (19)	0.05137 (12)
Cl2	0.76232 (3)	−0.03099 (3)	0.569340 (18)	0.05382 (13)
C11	0.54290 (10)	0.29825 (10)	0.65172 (6)	0.0359 (3)
C12	0.55854 (11)	0.30418 (11)	0.71586 (6)	0.0415 (4)
H12	0.4998	0.3071	0.7384	0.05*
C13	0.64578 (11)	0.30582 (11)	0.74530 (6)	0.0420 (3)
H13	0.6379	0.31	0.7857	0.05*
C14	0.75294 (11)	0.30223 (11)	0.72582 (7)	0.0410 (3)
C15	0.41539 (10)	0.31099 (9)	0.57492 (6)	0.0349 (3)
C16	0.32356 (11)	0.27102 (9)	0.55905 (7)	0.0366 (3)
C17	0.29294 (12)	0.26877 (10)	0.50117 (7)	0.0444 (4)
H17	0.2322	0.2405	0.491	0.053*
C18	0.35224 (13)	0.30829 (11)	0.45862 (7)	0.0471 (4)
H18	0.3326	0.3062	0.4195	0.057*
C19	0.44124 (12)	0.35108 (10)	0.47466 (7)	0.0423 (4)
C20	0.47341 (11)	0.35263 (10)	0.53203 (7)	0.0397 (3)
H20	0.5339	0.3815	0.5419	0.048*
N2	0.44678 (9)	0.31040 (9)	0.63412 (5)	0.0386 (3)
H2N	0.4011	0.3184	0.6606	0.046*
O4	0.61248 (8)	0.28343 (8)	0.61652 (4)	0.0496 (3)
O5	0.77523 (8)	0.28321 (10)	0.67163 (5)	0.0590 (3)
H5A	0.7227	0.2744	0.6532	0.089*
O6	0.81990 (9)	0.31650 (10)	0.76074 (6)	0.0696 (4)
Cl3	0.24556 (3)	0.22391 (3)	0.61215 (2)	0.05196 (12)
Cl4	0.51489 (4)	0.40468 (4)	0.42195 (2)	0.06528 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0294 (8)	0.0400 (8)	0.0355 (8)	0.0015 (6)	0.0014 (6)	0.0035 (6)
C2	0.0301 (8)	0.0553 (9)	0.0390 (8)	−0.0023 (6)	−0.0013 (6)	−0.0030 (7)
C3	0.0413 (8)	0.0563 (9)	0.0347 (8)	−0.0033 (7)	0.0042 (7)	−0.0038 (7)
C4	0.0385 (8)	0.0509 (9)	0.0431 (9)	0.0007 (7)	0.0099 (7)	0.0071 (7)
C5	0.0272 (7)	0.0384 (7)	0.0362 (7)	0.0001 (6)	0.0043 (6)	−0.0015 (6)
C6	0.0296 (7)	0.0363 (7)	0.0434 (8)	0.0015 (6)	0.0032 (6)	0.0027 (6)
C7	0.0366 (8)	0.0384 (8)	0.0494 (9)	0.0028 (6)	0.0099 (7)	−0.0059 (7)
C8	0.0443 (8)	0.0428 (8)	0.0376 (8)	−0.0030 (7)	0.0086 (7)	−0.0067 (6)
C9	0.0365 (8)	0.0389 (8)	0.0369 (8)	−0.0043 (6)	0.0000 (6)	0.0017 (6)
C10	0.0303 (7)	0.0398 (8)	0.0390 (8)	0.0046 (6)	0.0033 (6)	−0.0005 (6)
N1	0.0269 (6)	0.0513 (7)	0.0346 (6)	0.0040 (5)	−0.0002 (5)	−0.0021 (5)
O1	0.0311 (6)	0.0708 (7)	0.0381 (6)	−0.0067 (5)	0.0014 (5)	−0.0048 (5)
O2	0.0323 (6)	0.1000 (10)	0.0524 (7)	−0.0044 (6)	0.0077 (5)	−0.0069 (7)
O3	0.0476 (7)	0.0808 (9)	0.0523 (7)	−0.0011 (6)	0.0219 (6)	−0.0027 (6)
Cl1	0.0399 (2)	0.0602 (3)	0.0540 (2)	0.01679 (18)	−0.00180 (18)	0.00427 (19)
Cl2	0.0543 (3)	0.0671 (3)	0.0401 (2)	0.0055 (2)	−0.00553 (18)	0.00738 (18)
C11	0.0255 (7)	0.0469 (8)	0.0352 (8)	−0.0010 (6)	−0.0001 (6)	−0.0043 (6)
C12	0.0253 (7)	0.0661 (10)	0.0331 (8)	0.0018 (7)	0.0046 (6)	−0.0053 (7)
C13	0.0325 (8)	0.0634 (9)	0.0300 (7)	0.0007 (7)	0.0005 (6)	−0.0079 (7)
C14	0.0284 (7)	0.0562 (9)	0.0385 (8)	−0.0011 (6)	−0.0045 (7)	0.0018 (7)
C15	0.0275 (7)	0.0399 (8)	0.0371 (8)	0.0039 (6)	−0.0037 (6)	−0.0061 (6)
C16	0.0295 (7)	0.0344 (7)	0.0460 (8)	0.0021 (6)	−0.0031 (6)	−0.0047 (6)
C17	0.0375 (8)	0.0430 (9)	0.0528 (10)	0.0028 (7)	−0.0152 (7)	−0.0104 (7)
C18	0.0519 (10)	0.0502 (9)	0.0393 (8)	0.0115 (8)	−0.0133 (7)	−0.0074 (7)
C19	0.0418 (9)	0.0452 (8)	0.0398 (8)	0.0119 (7)	0.0017 (7)	0.0013 (7)
C20	0.0309 (8)	0.0447 (8)	0.0435 (9)	0.0003 (6)	−0.0019 (6)	−0.0039 (7)
N2	0.0242 (6)	0.0577 (8)	0.0339 (6)	0.0000 (5)	0.0004 (5)	−0.0058 (5)
O4	0.0305 (6)	0.0850 (8)	0.0334 (5)	0.0094 (5)	0.0014 (5)	−0.0056 (5)
O5	0.0273 (6)	0.1095 (10)	0.0403 (6)	0.0074 (6)	0.0025 (5)	−0.0009 (6)
O6	0.0334 (6)	0.1215 (11)	0.0539 (7)	−0.0072 (7)	−0.0134 (6)	−0.0058 (7)
Cl3	0.0386 (2)	0.0552 (3)	0.0621 (3)	−0.01198 (17)	0.00285 (18)	−0.00156 (19)
Cl4	0.0633 (3)	0.0810 (3)	0.0515 (3)	0.0115 (2)	0.0144 (2)	0.0150 (2)

Geometric parameters (Å, º) top

C1—O1	1.2364 (17)	C11—O4	1.2380 (17)
C1—N1	1.3378 (18)	C11—N2	1.3395 (18)
C1—C2	1.481 (2)	C11—C12	1.482 (2)
C2—C3	1.335 (2)	C12—C13	1.331 (2)
C2—H2	0.93	C12—H12	0.93
C3—C4	1.488 (2)	C13—C14	1.480 (2)
C3—H3	0.93	C13—H13	0.93
C4—O3	1.2143 (19)	C14—O6	1.2070 (19)
C4—O2	1.307 (2)	C14—O5	1.3024 (19)
C5—C10	1.386 (2)	C15—C20	1.385 (2)
C5—C6	1.3931 (19)	C15—C16	1.392 (2)
C5—N1	1.4168 (18)	C15—N2	1.4141 (18)
C6—C7	1.385 (2)	C16—C17	1.382 (2)
C6—Cl1	1.7298 (15)	C16—Cl3	1.7334 (15)
C7—C8	1.381 (2)	C17—C18	1.375 (2)
C7—H7	0.93	C17—H17	0.93
C8—C9	1.380 (2)	C18—C19	1.379 (2)
C8—H8	0.93	C18—H18	0.93
C9—C10	1.377 (2)	C19—C20	1.377 (2)
C9—Cl2	1.7397 (15)	C19—Cl4	1.7349 (16)
C10—H10	0.93	C20—H20	0.93
N1—H1N	0.86	N2—H2N	0.86
O2—H2A	0.82	O5—H5A	0.82

O1—C1—N1	122.16 (13)	O4—C11—N2	121.82 (13)
O1—C1—C2	123.52 (13)	O4—C11—C12	123.35 (13)
N1—C1—C2	114.32 (13)	N2—C11—C12	114.83 (12)
C3—C2—C1	128.59 (14)	C13—C12—C11	128.35 (13)
C3—C2—H2	115.7	C13—C12—H12	115.8
C1—C2—H2	115.7	C11—C12—H12	115.8
C2—C3—C4	132.31 (15)	C12—C13—C14	132.04 (14)
C2—C3—H3	113.8	C12—C13—H13	114
C4—C3—H3	113.8	C14—C13—H13	114
O3—C4—O2	120.55 (15)	O6—C14—O5	120.06 (14)
O3—C4—C3	118.83 (15)	O6—C14—C13	119.40 (14)
O2—C4—C3	120.62 (13)	O5—C14—C13	120.54 (13)
C10—C5—C6	119.12 (13)	C20—C15—C16	118.76 (13)
C10—C5—N1	121.19 (12)	C20—C15—N2	121.22 (13)
C6—C5—N1	119.59 (13)	C16—C15—N2	120.01 (13)
C7—C6—C5	120.54 (14)	C17—C16—C15	120.82 (14)
C7—C6—Cl1	119.15 (11)	C17—C16—Cl3	119.13 (12)
C5—C6—Cl1	120.30 (11)	C15—C16—Cl3	120.05 (11)
C8—C7—C6	120.24 (14)	C18—C17—C16	120.01 (14)
C8—C7—H7	119.9	C18—C17—H17	120
C6—C7—H7	119.9	C16—C17—H17	120
C9—C8—C7	118.71 (14)	C17—C18—C19	119.13 (14)
C9—C8—H8	120.6	C17—C18—H18	120.4
C7—C8—H8	120.6	C19—C18—H18	120.4
C10—C9—C8	121.93 (14)	C20—C19—C18	121.43 (15)
C10—C9—Cl2	118.56 (11)	C20—C19—Cl4	118.75 (13)
C8—C9—Cl2	119.50 (11)	C18—C19—Cl4	119.82 (12)
C9—C10—C5	119.44 (13)	C19—C20—C15	119.76 (14)
C9—C10—H10	120.3	C19—C20—H20	120.1
C5—C10—H10	120.3	C15—C20—H20	120.1
C1—N1—C5	125.22 (12)	C11—N2—C15	124.31 (12)
C1—N1—H1N	117.4	C11—N2—H2N	117.8
C5—N1—H1N	117.4	C15—N2—H2N	117.8
C4—O2—H2A	109.5	C14—O5—H5A	109.5

O1—C1—C2—C3	−0.1 (3)	O4—C11—C12—C13	8.6 (3)
N1—C1—C2—C3	179.57 (16)	N2—C11—C12—C13	−171.30 (16)
C1—C2—C3—C4	0.2 (3)	C11—C12—C13—C14	−0.2 (3)
C2—C3—C4—O3	178.25 (18)	C12—C13—C14—O6	170.54 (18)
C2—C3—C4—O2	−1.7 (3)	C12—C13—C14—O5	−10.0 (3)
C10—C5—C6—C7	−1.1 (2)	C20—C15—C16—C17	3.2 (2)
N1—C5—C6—C7	175.32 (13)	N2—C15—C16—C17	−178.24 (13)
C10—C5—C6—Cl1	179.64 (11)	C20—C15—C16—Cl3	−176.38 (11)
N1—C5—C6—Cl1	−3.89 (19)	N2—C15—C16—Cl3	2.19 (18)
C5—C6—C7—C8	0.5 (2)	C15—C16—C17—C18	−1.6 (2)
Cl1—C6—C7—C8	179.72 (11)	Cl3—C16—C17—C18	177.97 (11)
C6—C7—C8—C9	0.1 (2)	C16—C17—C18—C19	−1.0 (2)
C7—C8—C9—C10	0.0 (2)	C17—C18—C19—C20	2.0 (2)
C7—C8—C9—Cl2	−179.39 (11)	C17—C18—C19—Cl4	−177.81 (12)
C8—C9—C10—C5	−0.6 (2)	C18—C19—C20—C15	−0.4 (2)
Cl2—C9—C10—C5	178.73 (11)	Cl4—C19—C20—C15	179.43 (11)
C6—C5—C10—C9	1.2 (2)	C16—C15—C20—C19	−2.2 (2)
N1—C5—C10—C9	−175.21 (13)	N2—C15—C20—C19	179.26 (13)
O1—C1—N1—C5	−3.4 (2)	O4—C11—N2—C15	−2.4 (2)
C2—C1—N1—C5	176.88 (13)	C12—C11—N2—C15	177.50 (13)
C10—C5—N1—C1	−45.1 (2)	C20—C15—N2—C11	−39.9 (2)
C6—C5—N1—C1	138.55 (15)	C16—C15—N2—C11	141.55 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.86	2.07	2.8938 (17)	160
N2—H2N···O6ⁱⁱ	0.86	2.09	2.9263 (17)	164
O2—H2A···O1	0.82	1.68	2.4979 (15)	175
O5—H5A···O4	0.82	1.68	2.4846 (15)	166
C7—H7···Cg2	0.93	2.77	3.6745 (15)	163
C18—H18···O5ⁱⁱⁱ	0.93	2.58	3.4186 (19)	151
C20—H20···O4	0.93	2.46	2.8477 (18)	105

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

Experimental details

Crystal data
Chemical formula	C₁₀H₇Cl₂NO₃
M_r	260.07
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	295
a, b, c (Å)	13.1618 (2), 14.6993 (2), 22.8406 (3)
V (Å³)	4418.95 (11)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.58
Crystal size (mm)	0.40 × 0.33 × 0.24

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Analytical (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.836, 0.892
No. of measured, independent and observed [I > 2σ(I)] reflections	61823, 4191, 3514
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.079, 1.08
No. of reflections	4191
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.25

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.86	2.07	2.8938 (17)	160
N2—H2N···O6ⁱⁱ	0.86	2.09	2.9263 (17)	164
O2—H2A···O1	0.82	1.68	2.4979 (15)	175
O5—H5A···O4	0.82	1.68	2.4846 (15)	166
C7—H7···Cg2	0.93	2.77	3.6745 (15)	163
C18—H18···O5ⁱⁱⁱ	0.93	2.58	3.4186 (19)	151
C20—H20···O4	0.93	2.46	2.8477 (18)	105

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

Acknowledgements

MT and JK thank the Grant Agency of the Slovak Republic (VEGA 1/0817/08) and Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer.

References

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