2,4-Di­chloro-N-(2,5-dioxopyrrolidin-1-yl)benzamide

In the title compound, C₁₁H₈Cl₂N₂O₃, the plane of the pyrrolidine ring (r.m.s. deviation = 0.065 Å) makes a dihedral angle of 52.9 (2)° with the plane of the benzene ring. The least-squares plane of the central amide fragment makes dihedral angles of 49.3 (7) and 77.9 (7)° with those of the benzene and pyrrolidine rings, respectively. In the crystal, mol­ecules are linked via N—H...O hydrogen bonds, forming chains along the b-axis direction. π–π inter­actions link these chains into a two-dimensional network parallel to (100).

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.102
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          6 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: As the reported work is a part of collaboration between different Universities. Hence the number of authors are greater than 5. Synthesis has been carried out by S. Karanth, B. Narayana and B. K. Sarojini while Sumati Anthal and Jigmat Stondus are responsible for the data collection, refinement of the structure, Rajni Kant is responsible for structure completion in the form of paper and bearing the financial load for the publication.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

2,4-Dichloro-N-(2,5-dioxopyrrolidin-1-yl)benzamide

Crystal data

C11H8Cl2N2O3	F(000) = 584
Mr = 287.09	Dx = 1.622 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.8233 (5) Å	Cell parameters from 1764 reflections
b = 7.4705 (5) Å	θ = 3.8–28.5°
c = 20.1932 (12) Å	µ = 0.55 mm^−1
β = 94.866 (6)°	T = 293 K
V = 1175.92 (13) Å^3	Block, white
Z = 4	0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2306 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1790 reflections with I > 2σ(I)
Detector resolution: 16.1049 pixels mm^-1	Rint = 0.022
ω scans	θmax = 26.0°, θmin = 3.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	h = −5→9
Tmin = 0.843, Tmax = 1.000	k = −9→5
4484 measured reflections	l = −23→24

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.039	w = 1/[σ^2(Fo^2) + (0.0446P)^2 + 0.4192P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.102	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.27 e Å^−3
2306 reflections	Δρmin = −0.25 e Å^−3
164 parameters	Extinction correction: SHELXL2016 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.033 (3)

Special details

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. All the H-atoms were geometrically fixed and allowed to ride on their corresponding non-H atoms with Uiso(H)= 1.2Ueq(C/N).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.33079 (8)	0.67402 (9)	0.44687 (3)	0.0499 (2)
Cl2	−0.26441 (8)	0.82692 (10)	0.54467 (3)	0.0497 (2)
O3	−0.4599 (2)	0.4080 (3)	0.70363 (9)	0.0631 (6)
O2	−0.0342 (2)	0.6697 (2)	0.83595 (8)	0.0445 (4)
O1	−0.1790 (2)	0.8061 (2)	0.69526 (8)	0.0481 (5)
N2	−0.2154 (2)	0.5067 (2)	0.76313 (8)	0.0322 (4)
N1	−0.1163 (2)	0.5140 (2)	0.70973 (9)	0.0349 (5)
H1	−0.061713	0.421471	0.697493	0.042*
C8	−0.1680 (3)	0.5927 (3)	0.82315 (10)	0.0322 (5)
C9	−0.3159 (3)	0.5717 (3)	0.86544 (11)	0.0397 (6)
H9A	−0.354223	0.687723	0.879901	0.048*
H9B	−0.282461	0.499738	0.904372	0.048*
C10	−0.4579 (3)	0.4793 (4)	0.82189 (11)	0.0424 (6)
H10A	−0.484555	0.363709	0.840305	0.051*
H10B	−0.561064	0.551838	0.818213	0.051*
C11	−0.3888 (3)	0.4575 (3)	0.75525 (11)	0.0378 (5)
C7	−0.1084 (3)	0.6725 (3)	0.67729 (10)	0.0305 (5)
C1	0.0002 (3)	0.6678 (3)	0.61942 (10)	0.0283 (5)
C6	−0.0586 (3)	0.7415 (3)	0.55805 (10)	0.0302 (5)
C5	0.0427 (3)	0.7430 (3)	0.50520 (11)	0.0327 (5)
H5	0.001763	0.791103	0.464426	0.039*
C4	0.2062 (3)	0.6717 (3)	0.51414 (11)	0.0324 (5)
C3	0.2692 (3)	0.5985 (3)	0.57392 (12)	0.0364 (5)
H3	0.379787	0.552033	0.579194	0.044*
C2	0.1649 (3)	0.5952 (3)	0.62609 (11)	0.0341 (5)
H2	0.205534	0.543537	0.666277	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0441 (4)	0.0653 (5)	0.0439 (4)	0.0074 (3)	0.0241 (3)	0.0035 (3)
Cl2	0.0327 (3)	0.0773 (5)	0.0398 (4)	0.0180 (3)	0.0069 (2)	0.0149 (3)
O3	0.0549 (12)	0.0935 (16)	0.0397 (11)	−0.0197 (11)	−0.0030 (9)	−0.0141 (11)
O2	0.0408 (10)	0.0535 (10)	0.0383 (10)	−0.0099 (8)	−0.0018 (7)	−0.0023 (8)
O1	0.0596 (11)	0.0449 (10)	0.0427 (10)	0.0190 (9)	0.0213 (8)	0.0043 (8)
N2	0.0348 (10)	0.0410 (11)	0.0218 (9)	−0.0029 (8)	0.0073 (7)	−0.0005 (8)
N1	0.0423 (11)	0.0375 (10)	0.0268 (10)	0.0055 (8)	0.0136 (8)	0.0013 (9)
C8	0.0378 (13)	0.0337 (12)	0.0248 (11)	0.0013 (10)	0.0010 (9)	0.0029 (10)
C9	0.0451 (14)	0.0493 (14)	0.0257 (11)	0.0001 (11)	0.0090 (10)	−0.0004 (11)
C10	0.0370 (13)	0.0537 (15)	0.0376 (13)	−0.0044 (11)	0.0096 (10)	0.0023 (12)
C11	0.0379 (13)	0.0428 (13)	0.0324 (13)	−0.0047 (11)	0.0011 (10)	0.0005 (11)
C7	0.0294 (11)	0.0391 (12)	0.0230 (11)	0.0035 (9)	0.0021 (8)	0.0013 (10)
C1	0.0277 (11)	0.0322 (11)	0.0256 (11)	0.0015 (9)	0.0059 (8)	−0.0007 (9)
C6	0.0254 (11)	0.0357 (11)	0.0297 (11)	0.0023 (9)	0.0035 (9)	0.0029 (10)
C5	0.0341 (12)	0.0405 (12)	0.0240 (11)	0.0006 (10)	0.0053 (9)	0.0028 (10)
C4	0.0316 (11)	0.0359 (12)	0.0311 (12)	−0.0020 (10)	0.0115 (9)	−0.0028 (10)
C3	0.0266 (11)	0.0416 (13)	0.0415 (13)	0.0071 (10)	0.0066 (10)	−0.0016 (11)
C2	0.0323 (12)	0.0397 (13)	0.0301 (12)	0.0061 (10)	0.0010 (9)	0.0031 (10)

Geometric parameters (Å, º)

Cl1—C4	1.738 (2)	C10—C11	1.501 (3)
Cl2—C6	1.732 (2)	C10—H10A	0.9700
O3—C11	1.198 (3)	C10—H10B	0.9700
O2—C8	1.203 (3)	C7—C1	1.502 (3)
O1—C7	1.212 (3)	C1—C2	1.394 (3)
N2—N1	1.381 (2)	C1—C6	1.398 (3)
N2—C8	1.394 (3)	C6—C5	1.382 (3)
N2—C11	1.402 (3)	C5—C4	1.383 (3)
N1—C7	1.357 (3)	C5—H5	0.9300
N1—H1	0.8600	C4—C3	1.378 (3)
C8—C9	1.503 (3)	C3—C2	1.386 (3)
C9—C10	1.522 (3)	C3—H3	0.9300
C9—H9A	0.9700	C2—H2	0.9300
C9—H9B	0.9700
N1—N2—C8	122.35 (18)	N2—C11—C10	106.75 (18)
N1—N2—C11	121.57 (17)	O1—C7—N1	122.24 (19)
C8—N2—C11	113.77 (17)	O1—C7—C1	123.7 (2)
C7—N1—N2	117.59 (17)	N1—C7—C1	114.07 (18)
C7—N1—H1	121.2	C2—C1—C6	118.07 (19)
N2—N1—H1	121.2	C2—C1—C7	120.84 (19)
O2—C8—N2	124.7 (2)	C6—C1—C7	121.05 (18)
O2—C8—C9	128.7 (2)	C5—C6—C1	121.40 (19)
N2—C8—C9	106.57 (19)	C5—C6—Cl2	117.57 (16)
C8—C9—C10	106.14 (18)	C1—C6—Cl2	120.99 (16)
C8—C9—H9A	110.5	C6—C5—C4	118.7 (2)
C10—C9—H9A	110.5	C6—C5—H5	120.6
C8—C9—H9B	110.5	C4—C5—H5	120.6
C10—C9—H9B	110.5	C3—C4—C5	121.7 (2)
H9A—C9—H9B	108.7	C3—C4—Cl1	120.41 (17)
C11—C10—C9	105.48 (18)	C5—C4—Cl1	117.90 (17)
C11—C10—H10A	110.6	C4—C3—C2	118.9 (2)
C9—C10—H10A	110.6	C4—C3—H3	120.6
C11—C10—H10B	110.6	C2—C3—H3	120.6
C9—C10—H10B	110.6	C3—C2—C1	121.2 (2)
H10A—C10—H10B	108.8	C3—C2—H2	119.4
O3—C11—N2	123.6 (2)	C1—C2—H2	119.4
O3—C11—C10	129.7 (2)
C8—N2—N1—C7	−70.5 (3)	O1—C7—C1—C2	128.9 (2)
C11—N2—N1—C7	91.2 (2)	N1—C7—C1—C2	−48.9 (3)
N1—N2—C8—O2	−5.2 (3)	O1—C7—C1—C6	−48.9 (3)
C11—N2—C8—O2	−168.2 (2)	N1—C7—C1—C6	133.3 (2)
N1—N2—C8—C9	173.64 (19)	C2—C1—C6—C5	0.0 (3)
C11—N2—C8—C9	10.7 (2)	C7—C1—C6—C5	177.8 (2)
O2—C8—C9—C10	174.2 (2)	C2—C1—C6—Cl2	177.57 (17)
N2—C8—C9—C10	−4.6 (2)	C7—C1—C6—Cl2	−4.6 (3)
C8—C9—C10—C11	−2.3 (3)	C1—C6—C5—C4	−0.8 (3)
N1—N2—C11—O3	4.9 (4)	Cl2—C6—C5—C4	−178.47 (17)
C8—N2—C11—O3	168.0 (2)	C6—C5—C4—C3	0.5 (3)
N1—N2—C11—C10	−175.33 (19)	C6—C5—C4—Cl1	179.68 (17)
C8—N2—C11—C10	−12.2 (3)	C5—C4—C3—C2	0.6 (3)
C9—C10—C11—O3	−171.9 (3)	Cl1—C4—C3—C2	−178.55 (17)
C9—C10—C11—N2	8.3 (3)	C4—C3—C2—C1	−1.4 (3)
N2—N1—C7—O1	2.9 (3)	C6—C1—C2—C3	1.2 (3)
N2—N1—C7—C1	−179.25 (18)	C7—C1—C2—C3	−176.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.86	2.15	3.006 (3)	171

Symmetry code: (i) −x, y−1/2, −z+3/2.