4-(4,5,6,7-Tetra­chloro-1,3-dioxoisoindolin-2-yl)­benz­aldehyde

The title compound, C₁₅H₅Cl₄NO₃, was synthesized from tetra­chloro­phthalic anhydride and 4-amino­benz­aldehyde. In the mol­ecule, the tetra­chloro­phthal­imide unit is nearly planar and makes a dihedral angle of 56.20 (3)° with the benzene ring.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.030
• wR factor = 0.085
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT431_ALERT_2_B Short Inter HL..A Contact  Cl1    ..  O2      ..       2.90 Ang.
PLAT431_ALERT_2_B Short Inter HL..A Contact  Cl2    ..  O3      ..       2.89 Ang.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-III(Burnett & Johnson, 1996); ORTEP-3 for Windows(Farrugia, 1997); PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL.

4-(4,5,6,7-tetrachloro-1,3-dioxoisoindolin-2-yl)benzaldehyde

Crystal data

C15H5Cl4NO3	F(000) = 776
Mr = 389	Dx = 1.705 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4015 reflections
a = 12.6686 (10) Å	θ = 2.7–27.8°
b = 8.9057 (7) Å	µ = 0.79 mm^−1
c = 13.4400 (11) Å	T = 293 K
β = 91.737 (1)°	Block, colorless
V = 1515.6 (2) Å^3	0.28 × 0.22 × 0.18 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	3619 independent reflections
Radiation source: fine-focus sealed tube	2932 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
φ and ω scans	θmax = 27.9°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −15→16
Tmin = 0.801, Tmax = 0.867	k = −11→11
9918 measured reflections	l = −17→12

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.030	w = 1/[σ^2(Fo^2) + (0.0497P)^2 + 0.0714P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.085	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.25 e Å^−3
3619 reflections	Δρmin = −0.34 e Å^−3
208 parameters

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.88128 (4)	0.76476 (4)	0.12379 (3)	0.04384 (12)
Cl2	1.12468 (3)	0.70786 (5)	0.13137 (3)	0.04427 (12)
Cl3	1.21189 (3)	0.38355 (5)	0.13027 (3)	0.04846 (13)
Cl4	1.05704 (3)	0.10925 (4)	0.12373 (3)	0.04098 (12)
N1	0.72161 (10)	0.29949 (14)	0.11662 (10)	0.0370 (3)
O1	0.68065 (9)	0.55199 (13)	0.11447 (10)	0.0498 (3)
O2	0.81341 (9)	0.07618 (12)	0.11842 (10)	0.0467 (3)
O3	0.29063 (12)	−0.07076 (19)	0.15452 (14)	0.0774 (5)
C1	0.74447 (12)	0.45412 (16)	0.11736 (11)	0.0348 (3)
C2	0.86296 (11)	0.46221 (16)	0.12188 (10)	0.0311 (3)
C3	0.92941 (12)	0.58498 (16)	0.12445 (11)	0.0328 (3)
C4	1.03815 (12)	0.55868 (16)	0.12761 (10)	0.0334 (3)
C5	1.07789 (12)	0.41240 (17)	0.12754 (11)	0.0331 (3)
C6	1.00958 (12)	0.28979 (16)	0.12464 (10)	0.0315 (3)
C7	0.90305 (11)	0.31795 (16)	0.12250 (10)	0.0299 (3)
C8	0.81240 (11)	0.21009 (16)	0.11921 (11)	0.0328 (3)
C9	0.61778 (12)	0.23670 (18)	0.11448 (12)	0.0376 (3)
C10	0.54712 (13)	0.2727 (2)	0.03843 (14)	0.0476 (4)
H10	0.5648	0.3421	−0.0100	0.057*
C11	0.44882 (13)	0.2034 (2)	0.03526 (15)	0.0496 (4)
H11	0.4001	0.2272	−0.0154	0.060*
C12	0.42306 (12)	0.10010 (19)	0.10645 (14)	0.0442 (4)
C13	0.49414 (14)	0.0676 (2)	0.18396 (15)	0.0542 (5)
H13	0.4761	−0.0006	0.2331	0.065*
C14	0.59139 (14)	0.1364 (2)	0.18803 (15)	0.0523 (5)
H14	0.6392	0.1155	0.2401	0.063*
C15	0.32021 (14)	0.0222 (2)	0.09831 (16)	0.0536 (5)
H15	0.2751	0.0478	0.0451	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0558 (2)	0.02470 (18)	0.0511 (2)	−0.00035 (16)	0.00265 (19)	0.00030 (15)
Cl2	0.0480 (2)	0.0386 (2)	0.0463 (2)	−0.01880 (17)	0.00249 (18)	−0.00332 (16)
Cl3	0.0292 (2)	0.0532 (3)	0.0631 (3)	−0.00588 (16)	0.00306 (18)	−0.0039 (2)
Cl4	0.0362 (2)	0.0322 (2)	0.0547 (3)	0.00445 (14)	0.00383 (17)	0.00155 (16)
N1	0.0284 (6)	0.0309 (7)	0.0519 (8)	−0.0026 (5)	0.0028 (6)	0.0042 (6)
O1	0.0395 (6)	0.0355 (6)	0.0747 (9)	0.0074 (5)	0.0062 (6)	0.0090 (6)
O2	0.0380 (6)	0.0272 (6)	0.0749 (9)	−0.0040 (5)	0.0012 (6)	0.0005 (5)
O3	0.0485 (8)	0.0688 (10)	0.1146 (13)	−0.0236 (7)	−0.0010 (8)	0.0064 (9)
C1	0.0337 (8)	0.0297 (7)	0.0411 (8)	−0.0001 (6)	0.0048 (6)	0.0044 (6)
C2	0.0330 (7)	0.0275 (7)	0.0329 (7)	−0.0015 (5)	0.0034 (6)	0.0018 (6)
C3	0.0412 (8)	0.0253 (6)	0.0320 (7)	−0.0039 (6)	0.0031 (6)	0.0000 (5)
C4	0.0389 (8)	0.0326 (7)	0.0288 (7)	−0.0120 (6)	0.0029 (6)	−0.0012 (6)
C5	0.0293 (7)	0.0393 (8)	0.0309 (7)	−0.0042 (6)	0.0025 (6)	−0.0005 (6)
C6	0.0336 (7)	0.0284 (7)	0.0325 (7)	−0.0005 (5)	0.0024 (6)	0.0006 (6)
C7	0.0313 (7)	0.0272 (7)	0.0314 (7)	−0.0026 (5)	0.0028 (6)	0.0011 (5)
C8	0.0293 (7)	0.0294 (7)	0.0397 (8)	−0.0031 (6)	0.0020 (6)	0.0008 (6)
C9	0.0277 (7)	0.0349 (8)	0.0503 (9)	−0.0019 (6)	0.0030 (6)	0.0020 (7)
C10	0.0380 (9)	0.0443 (9)	0.0602 (11)	0.0000 (7)	−0.0011 (8)	0.0143 (8)
C11	0.0329 (8)	0.0527 (10)	0.0626 (11)	0.0036 (7)	−0.0090 (8)	0.0051 (9)
C12	0.0284 (8)	0.0412 (9)	0.0628 (11)	−0.0004 (6)	0.0019 (7)	−0.0039 (8)
C13	0.0387 (9)	0.0587 (11)	0.0649 (12)	−0.0143 (8)	−0.0003 (8)	0.0173 (9)
C14	0.0347 (9)	0.0624 (11)	0.0594 (11)	−0.0126 (8)	−0.0067 (8)	0.0183 (9)
C15	0.0334 (9)	0.0471 (10)	0.0803 (13)	−0.0048 (8)	0.0006 (8)	−0.0087 (10)

Geometric parameters (Å, º)

Cl1—C3	1.7132 (15)	C5—C6	1.393 (2)
Cl2—C4	1.7222 (14)	C6—C7	1.372 (2)
Cl3—C5	1.7162 (16)	C7—C8	1.4968 (19)
Cl4—C6	1.7168 (14)	C9—C10	1.376 (2)
N1—C8	1.3984 (19)	C9—C14	1.381 (2)
N1—C1	1.4071 (19)	C10—C11	1.389 (2)
N1—C9	1.4288 (19)	C10—H10	0.9300
O1—C1	1.1887 (18)	C11—C12	1.374 (3)
O2—C8	1.1927 (18)	C11—H11	0.9300
O3—C15	1.189 (2)	C12—C13	1.387 (2)
C1—C2	1.502 (2)	C12—C15	1.478 (2)
C2—C3	1.3796 (19)	C13—C14	1.376 (2)
C2—C7	1.381 (2)	C13—H13	0.9300
C3—C4	1.397 (2)	C14—H14	0.9300
C4—C5	1.397 (2)	C15—H15	0.9300
C8—N1—C1	112.84 (12)	O2—C8—N1	125.32 (13)
C8—N1—C9	122.25 (12)	O2—C8—C7	129.31 (14)
C1—N1—C9	124.91 (13)	N1—C8—C7	105.37 (12)
O1—C1—N1	125.29 (14)	C10—C9—C14	121.07 (15)
O1—C1—C2	130.09 (14)	C10—C9—N1	120.12 (14)
N1—C1—C2	104.62 (12)	C14—C9—N1	118.78 (14)
C3—C2—C7	120.86 (13)	C9—C10—C11	118.81 (16)
C3—C2—C1	130.33 (13)	C9—C10—H10	120.6
C7—C2—C1	108.80 (12)	C11—C10—H10	120.6
C2—C3—C4	117.93 (13)	C12—C11—C10	120.50 (16)
C2—C3—Cl1	121.58 (12)	C12—C11—H11	119.7
C4—C3—Cl1	120.49 (11)	C10—C11—H11	119.7
C5—C4—C3	120.77 (13)	C11—C12—C13	120.03 (15)
C5—C4—Cl2	119.37 (12)	C11—C12—C15	119.38 (17)
C3—C4—Cl2	119.86 (12)	C13—C12—C15	120.57 (17)
C6—C5—C4	120.49 (14)	C14—C13—C12	119.81 (17)
C6—C5—Cl3	119.77 (12)	C14—C13—H13	120.1
C4—C5—Cl3	119.74 (11)	C12—C13—H13	120.1
C7—C6—C5	117.85 (13)	C13—C14—C9	119.72 (16)
C7—C6—Cl4	121.03 (11)	C13—C14—H14	120.1
C5—C6—Cl4	121.12 (12)	C9—C14—H14	120.1
C6—C7—C2	122.09 (13)	O3—C15—C12	125.05 (19)
C6—C7—C8	129.54 (13)	O3—C15—H15	117.5
C2—C7—C8	108.36 (12)	C12—C15—H15	117.5
C8—N1—C1—O1	179.14 (16)	C3—C2—C7—C6	−0.7 (2)
C9—N1—C1—O1	−1.4 (3)	C1—C2—C7—C6	178.87 (14)
C8—N1—C1—C2	−0.58 (17)	C3—C2—C7—C8	−179.98 (13)
C9—N1—C1—C2	178.84 (14)	C1—C2—C7—C8	−0.44 (16)
O1—C1—C2—C3	0.4 (3)	C1—N1—C8—O2	−179.40 (16)
N1—C1—C2—C3	−179.90 (15)	C9—N1—C8—O2	1.2 (3)
O1—C1—C2—C7	−179.08 (17)	C1—N1—C8—C7	0.33 (18)
N1—C1—C2—C7	0.62 (16)	C9—N1—C8—C7	−179.10 (14)
C7—C2—C3—C4	0.0 (2)	C6—C7—C8—O2	0.6 (3)
C1—C2—C3—C4	−179.38 (14)	C2—C7—C8—O2	179.80 (16)
C7—C2—C3—Cl1	−179.97 (11)	C6—C7—C8—N1	−179.15 (15)
C1—C2—C3—Cl1	0.6 (2)	C2—C7—C8—N1	0.09 (17)
C2—C3—C4—C5	0.4 (2)	C8—N1—C9—C10	−123.09 (18)
Cl1—C3—C4—C5	−179.60 (11)	C1—N1—C9—C10	57.6 (2)
C2—C3—C4—Cl2	−179.76 (11)	C8—N1—C9—C14	54.9 (2)
Cl1—C3—C4—Cl2	0.26 (18)	C1—N1—C9—C14	−124.45 (18)
C3—C4—C5—C6	−0.2 (2)	C14—C9—C10—C11	−1.5 (3)
Cl2—C4—C5—C6	179.93 (11)	N1—C9—C10—C11	176.42 (16)
C3—C4—C5—Cl3	179.38 (11)	C9—C10—C11—C12	−0.5 (3)
Cl2—C4—C5—Cl3	−0.48 (18)	C10—C11—C12—C13	2.0 (3)
C4—C5—C6—C7	−0.4 (2)	C10—C11—C12—C15	−176.75 (17)
Cl3—C5—C6—C7	−179.98 (11)	C11—C12—C13—C14	−1.5 (3)
C4—C5—C6—Cl4	179.59 (11)	C15—C12—C13—C14	177.19 (19)
Cl3—C5—C6—Cl4	0.00 (18)	C12—C13—C14—C9	−0.4 (3)
C5—C6—C7—C2	0.8 (2)	C10—C9—C14—C13	2.0 (3)
Cl4—C6—C7—C2	−179.15 (11)	N1—C9—C14—C13	−175.99 (18)
C5—C6—C7—C8	179.98 (14)	C11—C12—C15—O3	178.7 (2)
Cl4—C6—C7—C8	0.0 (2)	C13—C12—C15—O3	−0.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1^i	0.93	2.57	3.359 (2)	143

Symmetry code: (i) −x+1, −y+1, −z.