4-[Bis(2-chloro­eth­yl)amino]­benzaldehyde

In the title compound, C₁₁H₁₃Cl₂NO, the chloroethyl amino groups are twisted with respect to the amino group, with N—C—C—Cl torsion angles of −177.4 (4) and 179.2 (3)°. The carbonyl group lies in the plane of the benzene ring to which it is attached; torsion angles C_ar—C_ar—C=O are 0.1 (8) and −178.2 (5)°. In the crystal, C—H...Cl and C—H...O hydrogen bonds link the mol­ecules, forming sheets parallel to (20-1). The sheets are linked by C—H...π inter­actions, forming a three-dimensional framework.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.038
• wR factor = 0.103
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00589 Ang.
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Note

Alert level G
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT128_ALERT_4_G Alternate Setting for Input Space Group  Cc              Ia Note
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          86 % Note

   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
   4 ALERT level G = General information/check it is not something unexpected

   1 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
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

(I)

Crystal data

C11H13Cl2NO	F(000) = 512
Mr = 246.12	Dx = 1.345 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 14.7725 (5) Å	Cell parameters from 2835 reflections
b = 9.3588 (3) Å	θ = 2.7–26.2°
c = 9.8079 (3) Å	µ = 0.51 mm^−1
β = 116.3080 (14)°	T = 296 K
V = 1215.52 (7) Å^3	Block, violet
Z = 4	0.35 × 0.22 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer	1926 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.013
Absorption correction: multi-scan (SADABS; Bruker, 2014)	θmax = 25.0°, θmin = 2.7°
Tmin = 0.842, Tmax = 0.951	h = −17→17
4392 measured reflections	k = −11→11
2044 independent reflections	l = −11→11

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0553P)^2 + 0.7925P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
2044 reflections	Δρmax = 0.25 e Å^−3
136 parameters	Δρmin = −0.29 e Å^−3
2 restraints	Absolute structure: Flack x determined using 848 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.08 (2)

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.

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

	x	y	z	Uiso*/Ueq
C1	0.6673 (3)	0.3236 (4)	0.2692 (4)	0.0449 (8)
H1	0.6576	0.2252	0.2634	0.054*
C2	0.7354 (3)	0.3839 (5)	0.4026 (4)	0.0514 (9)
H2	0.7704	0.3253	0.4863	0.062*
C3	0.7538 (3)	0.5297 (5)	0.4168 (4)	0.0499 (9)
C4	0.7002 (3)	0.6147 (4)	0.2902 (4)	0.0473 (9)
H4	0.7113	0.7128	0.2968	0.057*
C5	0.6309 (3)	0.5565 (4)	0.1552 (4)	0.0432 (8)
H5	0.5961	0.6159	0.0721	0.052*
C6	0.6119 (3)	0.4089 (4)	0.1410 (4)	0.0379 (7)
C7	0.8248 (4)	0.5912 (6)	0.5606 (5)	0.0729 (13)
H7	0.8581	0.5279	0.6404	0.087*
C8	0.4888 (3)	0.4367 (4)	−0.1290 (4)	0.0476 (8)
H8A	0.4717	0.3777	−0.2184	0.057*
H8B	0.5330	0.5127	−0.1306	0.057*
C9	0.3941 (4)	0.5004 (6)	−0.1334 (5)	0.0649 (11)
H9A	0.4110	0.5636	−0.0472	0.078*
H9B	0.3507	0.4252	−0.1279	0.078*
C10	0.5119 (3)	0.2010 (4)	−0.0036 (5)	0.0549 (9)
H10A	0.4420	0.1908	−0.0782	0.066*
H10B	0.5175	0.1689	0.0939	0.066*
C11	0.5779 (4)	0.1099 (5)	−0.0490 (6)	0.0673 (12)
H11A	0.6480	0.1203	0.0248	0.081*
H11B	0.5716	0.1403	−0.1474	0.081*
Cl1	0.33067 (14)	0.5973 (2)	−0.30549 (17)	0.1116 (7)
Cl2	0.54009 (14)	−0.07305 (13)	−0.0583 (2)	0.1026 (6)
N1	0.5415 (2)	0.3503 (3)	0.0072 (3)	0.0485 (8)
O1	0.8448 (3)	0.7153 (5)	0.5867 (4)	0.1042 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0492 (19)	0.0381 (18)	0.0434 (18)	0.0023 (15)	0.0169 (15)	0.0023 (15)
C2	0.046 (2)	0.064 (3)	0.0378 (19)	0.0090 (17)	0.0129 (17)	0.0093 (16)
C3	0.0434 (19)	0.064 (2)	0.0401 (18)	−0.0042 (18)	0.0163 (15)	−0.0097 (18)
C4	0.054 (2)	0.044 (2)	0.049 (2)	−0.0157 (16)	0.0269 (18)	−0.0147 (17)
C5	0.050 (2)	0.0394 (19)	0.0380 (18)	−0.0018 (15)	0.0178 (17)	0.0007 (15)
C6	0.0400 (16)	0.0358 (17)	0.0372 (16)	−0.0025 (14)	0.0164 (14)	−0.0039 (13)
C7	0.061 (3)	0.096 (4)	0.049 (3)	−0.013 (3)	0.014 (2)	−0.020 (2)
C8	0.051 (2)	0.049 (2)	0.0374 (17)	−0.0015 (16)	0.0155 (16)	−0.0061 (15)
C9	0.057 (2)	0.079 (3)	0.057 (2)	0.011 (2)	0.0236 (19)	0.007 (2)
C10	0.048 (2)	0.048 (2)	0.059 (2)	−0.0081 (17)	0.0150 (17)	−0.0059 (18)
C11	0.065 (3)	0.053 (2)	0.078 (3)	−0.0001 (19)	0.027 (2)	−0.011 (2)
Cl1	0.1303 (13)	0.1108 (12)	0.0692 (8)	0.0702 (10)	0.0221 (8)	0.0210 (8)
Cl2	0.1109 (11)	0.0428 (6)	0.1303 (13)	0.0013 (6)	0.0317 (9)	−0.0175 (7)
N1	0.0513 (17)	0.0396 (16)	0.0401 (16)	−0.0029 (13)	0.0071 (14)	−0.0009 (13)
O1	0.108 (3)	0.109 (4)	0.072 (2)	−0.041 (3)	0.018 (2)	−0.040 (2)

Geometric parameters (Å, º)

C1—C2	1.370 (5)	C8—N1	1.457 (5)
C1—C6	1.405 (5)	C8—C9	1.504 (6)
C1—H1	0.9300	C8—H8A	0.9700
C2—C3	1.385 (6)	C8—H8B	0.9700
C2—H2	0.9300	C9—Cl1	1.774 (5)
C3—C4	1.389 (6)	C9—H9A	0.9700
C3—C7	1.453 (6)	C9—H9B	0.9700
C4—C5	1.377 (5)	C10—N1	1.454 (5)
C4—H4	0.9300	C10—C11	1.503 (6)
C5—C6	1.405 (5)	C10—H10A	0.9700
C5—H5	0.9300	C10—H10B	0.9700
C6—N1	1.377 (4)	C11—Cl2	1.791 (5)
C7—O1	1.197 (7)	C11—H11A	0.9700
C7—H7	0.9300	C11—H11B	0.9700
C2—C1—C6	120.7 (3)	N1—C8—H8B	109.4
C2—C1—H1	119.6	C9—C8—H8B	109.4
C6—C1—H1	119.6	H8A—C8—H8B	108.0
C1—C2—C3	122.0 (3)	C8—C9—Cl1	108.9 (3)
C1—C2—H2	119.0	C8—C9—H9A	109.9
C3—C2—H2	119.0	Cl1—C9—H9A	109.9
C2—C3—C4	117.8 (3)	C8—C9—H9B	109.9
C2—C3—C7	120.8 (4)	Cl1—C9—H9B	109.9
C4—C3—C7	121.4 (4)	H9A—C9—H9B	108.3
C5—C4—C3	121.3 (4)	N1—C10—C11	110.7 (3)
C5—C4—H4	119.4	N1—C10—H10A	109.5
C3—C4—H4	119.4	C11—C10—H10A	109.5
C4—C5—C6	120.9 (3)	N1—C10—H10B	109.5
C4—C5—H5	119.5	C11—C10—H10B	109.5
C6—C5—H5	119.5	H10A—C10—H10B	108.1
N1—C6—C5	121.3 (3)	C10—C11—Cl2	109.2 (3)
N1—C6—C1	121.4 (3)	C10—C11—H11A	109.8
C5—C6—C1	117.3 (3)	Cl2—C11—H11A	109.8
O1—C7—C3	126.6 (5)	C10—C11—H11B	109.8
O1—C7—H7	116.7	Cl2—C11—H11B	109.8
C3—C7—H7	116.7	H11A—C11—H11B	108.3
N1—C8—C9	111.0 (3)	C6—N1—C10	121.9 (3)
N1—C8—H8A	109.4	C6—N1—C8	121.6 (3)
C9—C8—H8A	109.4	C10—N1—C8	116.5 (3)
C6—C1—C2—C3	−0.9 (6)	C4—C3—C7—O1	0.1 (8)
C1—C2—C3—C4	0.2 (6)	N1—C8—C9—Cl1	−177.4 (3)
C1—C2—C3—C7	178.6 (4)	N1—C10—C11—Cl2	179.2 (3)
C2—C3—C4—C5	0.2 (6)	C5—C6—N1—C10	−172.2 (3)
C7—C3—C4—C5	−178.2 (4)	C1—C6—N1—C10	7.4 (5)
C3—C4—C5—C6	0.1 (6)	C5—C6—N1—C8	4.7 (5)
C4—C5—C6—N1	178.8 (3)	C1—C6—N1—C8	−175.8 (3)
C4—C5—C6—C1	−0.8 (5)	C11—C10—N1—C6	−90.4 (4)
C2—C1—C6—N1	−178.4 (3)	C11—C10—N1—C8	92.6 (4)
C2—C1—C6—C5	1.2 (5)	C9—C8—N1—C6	−88.8 (5)
C2—C3—C7—O1	−178.2 (5)	C9—C8—N1—C10	88.2 (4)

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cl1^i	0.93	2.81	3.715 (5)	164
C8—H8A···O1^ii	0.97	2.51	3.367 (6)	147
C8—H8B···Cg^iii	0.97	2.73	3.482 (5)	134

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