N-(4-Amino-2-methyl­phenyl)-4-chloro­phthal­imide

In the title compound, C₁₅H₁₁ClN₂O₂, the benzene ring is twisted with respect to the phthal­imide plane. The mol­ecules are held together by intermolecular O...H—N hydrogen bonds, giving rise to a dimeric structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.053
• wR factor = 0.147
• Data-to-parameter ratio = 20.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor       N2     -   H2B    ...          ?
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C15 H11 Cl N2 O2

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

   0 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

N-(4-Amino-2-methylphenyl)-4-chlorophthalimide

Crystal data

C15H11ClN2O2	F(000) = 1184
Mr = 286.71	Dx = 1.449 Mg m^−3
Monoclinic, C2/c	Melting point = 208–210 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 23.624 (11) Å	Cell parameters from 25 reflections
b = 7.779 (5) Å	θ = 9.4–10.4°
c = 14.307 (14) Å	µ = 0.29 mm^−1
β = 90.72 (6)°	T = 293 K
V = 2629 (3) Å^3	Prism, yellow
Z = 8	0.56 × 0.48 × 0.28 mm

Data collection

Enraf-Nonius MACH3 four-circle (CAD-4) diffractometer	Rint = 0.037
Radiation source: fine-focus sealed tube	θmax = 30.0°, θmin = 1.7°
Graphite monochromator	h = 0→33
Profile data from ω scans	k = 0→10
3897 measured reflections	l = −20→20
3823 independent reflections	3 standard reflections every 90 min
2136 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0597P)^2 + 1.5745P] where P = (Fo^2 + 2Fc^2)/3
3823 reflections	(Δ/σ)max < 0.001
188 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

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	0.32015 (3)	0.14290 (10)	0.68512 (5)	0.0610 (2)
O1	0.10990 (7)	−0.2024 (2)	0.60643 (12)	0.0559 (5)
O2	0.16596 (8)	−0.1310 (3)	0.30363 (11)	0.0596 (5)
N1	0.12330 (8)	−0.1776 (3)	0.44620 (13)	0.0445 (5)
N2	−0.09652 (10)	−0.3683 (4)	0.33639 (18)	0.0610 (6)
H2A	−0.1143 (14)	−0.295 (5)	0.297 (2)	0.091*
H2B	−0.1003 (14)	−0.477 (5)	0.323 (2)	0.091*
C1	0.21279 (9)	−0.0590 (3)	0.45056 (15)	0.0405 (5)
C2	0.26439 (9)	0.0144 (3)	0.42980 (16)	0.0438 (5)
H2	0.2764	0.0240	0.3684	0.053*
C3	0.29761 (10)	0.0732 (3)	0.50391 (17)	0.0453 (6)
H3	0.3326	0.1233	0.4925	0.054*
C4	0.27871 (9)	0.0574 (3)	0.59492 (16)	0.0430 (5)
C5	0.22765 (10)	−0.0198 (3)	0.61695 (16)	0.0439 (5)
H5	0.2160	−0.0325	0.6784	0.053*
C6	0.19525 (9)	−0.0765 (3)	0.54213 (15)	0.0392 (5)
C7	0.13824 (10)	−0.1587 (3)	0.54105 (16)	0.0429 (5)
C8	0.16715 (10)	−0.1243 (3)	0.38760 (16)	0.0446 (5)
C9	0.06762 (9)	−0.2266 (3)	0.41368 (15)	0.0416 (5)
C10	0.02940 (10)	−0.0993 (3)	0.38596 (16)	0.0456 (6)
C11	−0.02470 (10)	−0.1510 (3)	0.35893 (17)	0.0489 (6)
H11	−0.0509	−0.0681	0.3404	0.059*
C12	−0.04090 (10)	−0.3220 (3)	0.35869 (15)	0.0438 (6)
C13	−0.00168 (11)	−0.4450 (3)	0.38521 (18)	0.0525 (6)
H13	−0.0116	−0.5607	0.3845	0.063*
C14	0.05229 (10)	−0.3962 (3)	0.41290 (18)	0.0504 (6)
H14	0.0784	−0.4795	0.4312	0.060*
C15	0.04537 (13)	0.0880 (3)	0.3836 (2)	0.0717 (9)
H15A	0.0680	0.1101	0.3296	0.107*
H15B	0.0667	0.1163	0.4391	0.107*
H15C	0.0117	0.1569	0.3807	0.107*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0550 (4)	0.0730 (5)	0.0546 (4)	−0.0050 (3)	−0.0108 (3)	−0.0017 (3)
O1	0.0497 (10)	0.0696 (12)	0.0488 (10)	−0.0055 (9)	0.0121 (8)	0.0075 (9)
O2	0.0553 (11)	0.0840 (14)	0.0396 (10)	−0.0148 (10)	0.0020 (8)	−0.0007 (9)
N1	0.0385 (10)	0.0526 (12)	0.0425 (10)	−0.0040 (9)	0.0046 (8)	0.0037 (9)
N2	0.0419 (12)	0.0770 (18)	0.0640 (15)	−0.0079 (13)	−0.0042 (10)	0.0061 (14)
C1	0.0391 (12)	0.0429 (13)	0.0396 (12)	0.0050 (10)	0.0029 (9)	−0.0010 (10)
C2	0.0391 (12)	0.0515 (14)	0.0411 (12)	0.0031 (11)	0.0074 (9)	0.0028 (11)
C3	0.0355 (11)	0.0483 (14)	0.0520 (13)	0.0013 (10)	0.0012 (10)	0.0035 (11)
C4	0.0399 (12)	0.0425 (13)	0.0465 (13)	0.0052 (10)	−0.0050 (10)	−0.0014 (10)
C5	0.0455 (13)	0.0476 (14)	0.0387 (12)	0.0056 (11)	0.0023 (9)	0.0022 (10)
C6	0.0359 (11)	0.0398 (13)	0.0419 (12)	0.0046 (10)	0.0049 (9)	0.0025 (10)
C7	0.0409 (12)	0.0438 (13)	0.0442 (12)	0.0033 (10)	0.0050 (10)	0.0022 (10)
C8	0.0428 (13)	0.0489 (14)	0.0424 (13)	0.0017 (11)	0.0034 (10)	0.0032 (11)
C9	0.0369 (11)	0.0457 (14)	0.0423 (12)	−0.0018 (10)	0.0018 (9)	0.0028 (10)
C10	0.0465 (13)	0.0417 (13)	0.0488 (13)	0.0018 (10)	0.0063 (10)	0.0036 (11)
C11	0.0415 (13)	0.0527 (15)	0.0525 (14)	0.0097 (12)	0.0022 (10)	0.0070 (12)
C12	0.0393 (12)	0.0556 (15)	0.0368 (11)	−0.0020 (11)	0.0052 (9)	0.0025 (11)
C13	0.0523 (15)	0.0391 (14)	0.0660 (16)	−0.0056 (11)	0.0005 (12)	0.0041 (12)
C14	0.0426 (13)	0.0445 (14)	0.0640 (16)	0.0052 (11)	−0.0006 (11)	0.0094 (12)
C15	0.0668 (19)	0.0404 (15)	0.108 (2)	−0.0006 (14)	−0.0012 (17)	0.0032 (16)

Geometric parameters (Å, º)

Cl1—C4	1.742 (3)	C5—C6	1.381 (3)
O1—C7	1.206 (3)	C5—H5	0.9300
O2—C8	1.203 (3)	C6—C7	1.491 (3)
N1—C8	1.404 (3)	C9—C14	1.368 (4)
N1—C7	1.406 (3)	C9—C10	1.395 (3)
N1—C9	1.441 (3)	C10—C11	1.390 (3)
N2—C12	1.395 (3)	C10—C15	1.505 (4)
N2—H2A	0.90 (3)	C11—C12	1.384 (4)
N2—H2B	0.87 (4)	C11—H11	0.9300
C1—C2	1.382 (3)	C12—C13	1.382 (3)
C1—C6	1.386 (3)	C13—C14	1.383 (3)
C1—C8	1.486 (3)	C13—H13	0.9300
C2—C3	1.389 (3)	C14—H14	0.9300
C2—H2	0.9300	C15—H15A	0.9600
C3—C4	1.387 (3)	C15—H15B	0.9600
C3—H3	0.9300	C15—H15C	0.9600
C4—C5	1.387 (3)
C8—N1—C7	111.56 (19)	O2—C8—N1	125.1 (2)
C8—N1—C9	124.25 (19)	O2—C8—C1	128.9 (2)
C7—N1—C9	123.82 (19)	N1—C8—C1	105.9 (2)
C12—N2—H2A	114 (2)	C14—C9—C10	120.8 (2)
C12—N2—H2B	113 (2)	C14—C9—N1	119.9 (2)
H2A—N2—H2B	115 (3)	C10—C9—N1	119.3 (2)
C2—C1—C6	121.3 (2)	C11—C10—C9	117.6 (2)
C2—C1—C8	130.3 (2)	C11—C10—C15	120.3 (2)
C6—C1—C8	108.4 (2)	C9—C10—C15	122.1 (2)
C1—C2—C3	117.6 (2)	C12—C11—C10	122.2 (2)
C1—C2—H2	121.2	C12—C11—H11	118.9
C3—C2—H2	121.2	C10—C11—H11	118.9
C4—C3—C2	120.1 (2)	C13—C12—C11	118.7 (2)
C4—C3—H3	119.9	C13—C12—N2	120.7 (2)
C2—C3—H3	119.9	C11—C12—N2	120.5 (2)
C5—C4—C3	122.9 (2)	C12—C13—C14	120.1 (2)
C5—C4—Cl1	118.63 (19)	C12—C13—H13	120.0
C3—C4—Cl1	118.48 (19)	C14—C13—H13	120.0
C6—C5—C4	115.9 (2)	C9—C14—C13	120.6 (2)
C6—C5—H5	122.0	C9—C14—H14	119.7
C4—C5—H5	122.0	C13—C14—H14	119.7
C5—C6—C1	122.1 (2)	C10—C15—H15A	109.5
C5—C6—C7	129.6 (2)	C10—C15—H15B	109.5
C1—C6—C7	108.3 (2)	H15A—C15—H15B	109.5
O1—C7—N1	125.7 (2)	C10—C15—H15C	109.5
O1—C7—C6	128.5 (2)	H15A—C15—H15C	109.5
N1—C7—C6	105.71 (19)	H15B—C15—H15C	109.5
C6—C1—C2—C3	−1.3 (4)	C7—N1—C8—C1	−2.6 (3)
C8—C1—C2—C3	176.3 (2)	C9—N1—C8—C1	170.6 (2)
C1—C2—C3—C4	0.0 (4)	C2—C1—C8—O2	2.0 (5)
C2—C3—C4—C5	1.6 (4)	C6—C1—C8—O2	179.8 (3)
C2—C3—C4—Cl1	−176.75 (18)	C2—C1—C8—N1	−177.4 (2)
C3—C4—C5—C6	−1.9 (4)	C6—C1—C8—N1	0.5 (3)
Cl1—C4—C5—C6	176.52 (17)	C8—N1—C9—C14	106.0 (3)
C4—C5—C6—C1	0.5 (3)	C7—N1—C9—C14	−81.6 (3)
C4—C5—C6—C7	−177.8 (2)	C8—N1—C9—C10	−76.0 (3)
C2—C1—C6—C5	1.0 (4)	C7—N1—C9—C10	96.5 (3)
C8—C1—C6—C5	−177.1 (2)	C14—C9—C10—C11	0.8 (3)
C2—C1—C6—C7	179.7 (2)	N1—C9—C10—C11	−177.2 (2)
C8—C1—C6—C7	1.6 (3)	C14—C9—C10—C15	−178.4 (3)
C8—N1—C7—O1	−176.0 (2)	N1—C9—C10—C15	3.5 (4)
C9—N1—C7—O1	10.7 (4)	C9—C10—C11—C12	−0.2 (4)
C8—N1—C7—C6	3.6 (3)	C15—C10—C11—C12	179.0 (3)
C9—N1—C7—C6	−169.7 (2)	C10—C11—C12—C13	−0.7 (4)
C5—C6—C7—O1	−5.0 (4)	C10—C11—C12—N2	176.2 (2)
C1—C6—C7—O1	176.4 (2)	C11—C12—C13—C14	1.1 (4)
C5—C6—C7—N1	175.4 (2)	N2—C12—C13—C14	−175.8 (2)
C1—C6—C7—N1	−3.1 (3)	C10—C9—C14—C13	−0.5 (4)
C7—N1—C8—O2	178.0 (2)	N1—C9—C14—C13	177.6 (2)
C9—N1—C8—O2	−8.7 (4)	C12—C13—C14—C9	−0.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2^i	0.90 (3)	2.27 (4)	3.167 (4)	174 (3)

Symmetry code: (i) −x, y, −z+1/2.