2-Chloro-N-[(4-chloro-phen-yl)(phen-yl)meth-yl]-N-[2-(4-nitro-1H-imidazol-1-yl)eth-yl]ethanamine.

In the title compound, C(20)H(20)Cl(2)N(4)O(2), the nitro-imidazole ring makes dihedral angles of 17.00 (1) and 60.45 (11)° with the phenyl and chloro-phenyl rings, respectively. The three-coordinate N atom connected to two methyl-ene and one methine C atoms shows pyramidal coordination.

Related literature

For the use of nitro­gen mustards containing the β-chloro­ethyl­amine unit as anti­tumor drugs, see: Zhuang et al. (2008 ▶). Nitro­imidazole compounds are also used extensively in the treatment of various cancers as clinical radiosensitizers, see: Cai et al. (2009 ▶). For the synthesis, see: Fang et al. (2010 ▶); Gan et al. (2010 ▶).

Experimental

Crystal data

C20H20Cl2N4O2

M = 419.30

Monoclinic,

a = 8.8206 (16) Å

b = 25.005 (5) Å

c = 9.0450 (17) Å

β = 100.802 (3)°

V = 1959.6 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 298 K

0.32 × 0.24 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.903, T max = 0.938

9838 measured reflections

3449 independent reflections

2464 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.139

S = 1.03

3449 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681100256X/ng5107sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100256X/ng5107Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H20Cl2N4O2	Z = 4
Mr = 419.30	F(000) = 872
Monoclinic, P21/n	Dx = 1.421 Mg m−3
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.8206 (16) Å	θ = 2.4–21.3°
b = 25.005 (5) Å	µ = 0.36 mm−1
c = 9.0450 (17) Å	T = 298 K
β = 100.802 (3)°	Block, colourless
V = 1959.6 (6) Å3	0.32 × 0.24 × 0.18 mm

Bruker SMART CCD area-detector diffractometer	3449 independent reflections
Radiation source: fine-focus sealed tube	2464 reflections with I > 2σ(I)
graphite	Rint = 0.037
phi and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→7
Tmin = 0.903, Tmax = 0.938	k = −29→29
9838 measured reflections	l = −10→10

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0576P)2 + 0.904P] where P = (Fo2 + 2Fc2)/3
3449 reflections	(Δ/σ)max = 0.001
253 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.3270 (3)	0.05952 (13)	0.0927 (3)	0.0487 (7)
C2	0.4173 (4)	0.01834 (13)	0.1569 (4)	0.0615 (9)
H2	0.3972	−0.0165	0.1231	0.074*
C3	0.5385 (4)	0.02915 (12)	0.2723 (3)	0.0538 (8)
H3	0.5994	0.0009	0.3161	0.065*
C4	0.5734 (3)	0.07989 (11)	0.3257 (3)	0.0402 (6)
C5	0.4771 (3)	0.12070 (12)	0.2588 (3)	0.0498 (7)
H5	0.4957	0.1556	0.2933	0.060*
C6	0.3544 (3)	0.11081 (12)	0.1423 (3)	0.0514 (8)
H6	0.2917	0.1386	0.0985	0.062*
C7	0.7143 (3)	0.08861 (11)	0.4496 (3)	0.0401 (6)
H7	0.7628	0.0533	0.4654	0.048*
C8	0.6827 (3)	0.10452 (10)	0.6032 (3)	0.0400 (6)
C9	0.8038 (3)	0.10174 (11)	0.7245 (3)	0.0456 (7)
H9	0.8999	0.0902	0.7091	0.055*
C10	0.7859 (4)	0.11550 (12)	0.8666 (3)	0.0536 (8)
H10	0.8695	0.1137	0.9463	0.064*
C11	0.6439 (4)	0.13203 (13)	0.8913 (4)	0.0592 (8)
H11	0.6313	0.1417	0.9875	0.071*
C12	0.5226 (4)	0.13412 (14)	0.7746 (4)	0.0657 (9)
H12	0.4263	0.1448	0.7912	0.079*
C13	0.5415 (3)	0.12044 (12)	0.6309 (3)	0.0538 (8)
H13	0.4573	0.1220	0.5518	0.065*
C14	0.9049 (3)	0.10277 (13)	0.2887 (3)	0.0547 (8)
H14A	0.9671	0.1308	0.2559	0.066*
H14B	0.8231	0.0941	0.2046	0.066*
C15	1.0037 (4)	0.05433 (13)	0.3272 (4)	0.0591 (8)
H15A	1.0457	0.0436	0.2400	0.071*
H15B	0.9407	0.0252	0.3526	0.071*
C16	0.7954 (3)	0.18032 (11)	0.3913 (3)	0.0498 (7)
H16A	0.7132	0.1884	0.4456	0.060*
H16B	0.7574	0.1876	0.2855	0.060*
C17	0.9333 (4)	0.21643 (13)	0.4485 (3)	0.0557 (8)
H17A	1.0205	0.2049	0.4051	0.067*
H17B	0.9081	0.2528	0.4158	0.067*
C18	1.1030 (3)	0.19238 (12)	0.6938 (4)	0.0523 (8)
H18	1.1775	0.1748	0.6516	0.063*
C19	0.9802 (3)	0.22472 (11)	0.8478 (3)	0.0479 (7)
C20	0.8953 (3)	0.23602 (11)	0.7104 (4)	0.0521 (8)
H20	0.8017	0.2542	0.6891	0.063*
Cl1	0.17478 (11)	0.04618 (4)	−0.05458 (11)	0.0835 (3)
Cl2	1.15787 (10)	0.06636 (4)	0.48090 (12)	0.0777 (3)
N1	0.8356 (2)	0.12352 (9)	0.4102 (2)	0.0412 (5)
N2	0.9760 (3)	0.21524 (9)	0.6115 (3)	0.0458 (6)
N3	1.1106 (3)	0.19743 (10)	0.8388 (3)	0.0538 (6)
N4	0.9403 (4)	0.23746 (13)	0.9901 (4)	0.0692 (8)
O1	1.0250 (3)	0.22177 (12)	1.1050 (3)	0.0897 (9)
O2	0.8228 (4)	0.26290 (15)	0.9864 (4)	0.1142 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0397 (16)	0.0603 (19)	0.0430 (17)	−0.0055 (14)	−0.0002 (13)	−0.0095 (14)
C2	0.059 (2)	0.0473 (18)	0.073 (2)	−0.0065 (16)	−0.0015 (18)	−0.0138 (16)
C3	0.0534 (18)	0.0446 (17)	0.060 (2)	0.0017 (14)	0.0013 (16)	−0.0014 (14)
C4	0.0360 (14)	0.0425 (15)	0.0416 (16)	0.0020 (12)	0.0059 (12)	0.0013 (12)
C5	0.0451 (16)	0.0416 (16)	0.0565 (19)	0.0023 (13)	−0.0061 (14)	−0.0055 (14)
C6	0.0427 (17)	0.0503 (18)	0.0561 (19)	0.0063 (14)	−0.0040 (14)	0.0038 (14)
C7	0.0361 (14)	0.0399 (15)	0.0417 (16)	0.0039 (12)	0.0005 (12)	0.0038 (12)
C8	0.0383 (15)	0.0369 (14)	0.0433 (16)	−0.0022 (12)	0.0041 (12)	0.0054 (12)
C9	0.0347 (15)	0.0561 (18)	0.0450 (17)	0.0012 (13)	0.0049 (13)	0.0102 (14)
C10	0.0498 (18)	0.068 (2)	0.0392 (17)	−0.0077 (16)	−0.0004 (14)	0.0072 (15)
C11	0.063 (2)	0.068 (2)	0.0475 (18)	−0.0007 (17)	0.0118 (16)	−0.0073 (16)
C12	0.0505 (19)	0.087 (3)	0.059 (2)	0.0159 (18)	0.0107 (17)	−0.0067 (18)
C13	0.0397 (16)	0.069 (2)	0.0493 (18)	0.0076 (15)	−0.0010 (14)	−0.0013 (15)
C14	0.0442 (17)	0.076 (2)	0.0419 (17)	−0.0036 (16)	0.0032 (14)	0.0063 (15)
C15	0.0513 (19)	0.072 (2)	0.057 (2)	−0.0036 (17)	0.0181 (16)	−0.0093 (17)
C16	0.0454 (17)	0.0521 (18)	0.0463 (17)	−0.0048 (14)	−0.0055 (14)	0.0111 (14)
C17	0.0549 (19)	0.0574 (19)	0.0500 (18)	−0.0139 (15)	−0.0022 (15)	0.0171 (15)
C18	0.0396 (16)	0.0621 (19)	0.054 (2)	0.0032 (15)	0.0060 (14)	0.0025 (15)
C19	0.0413 (16)	0.0467 (17)	0.0552 (19)	−0.0076 (14)	0.0074 (14)	−0.0049 (14)
C20	0.0404 (17)	0.0441 (17)	0.067 (2)	0.0010 (14)	−0.0030 (16)	−0.0054 (15)
Cl1	0.0626 (6)	0.0995 (7)	0.0751 (6)	−0.0043 (5)	−0.0216 (5)	−0.0236 (5)
Cl2	0.0537 (5)	0.0773 (6)	0.0937 (7)	0.0113 (4)	−0.0080 (5)	0.0054 (5)
N1	0.0341 (12)	0.0473 (13)	0.0411 (13)	0.0014 (10)	0.0038 (10)	0.0070 (10)
N2	0.0381 (13)	0.0465 (13)	0.0494 (15)	−0.0064 (11)	−0.0001 (11)	0.0047 (11)
N3	0.0452 (15)	0.0627 (16)	0.0507 (16)	−0.0013 (13)	0.0017 (12)	0.0051 (13)
N4	0.0560 (19)	0.080 (2)	0.072 (2)	−0.0215 (16)	0.0145 (17)	−0.0256 (17)
O1	0.094 (2)	0.117 (2)	0.0570 (16)	−0.0273 (18)	0.0125 (16)	−0.0085 (15)
O2	0.078 (2)	0.151 (3)	0.117 (3)	0.012 (2)	0.0262 (18)	−0.065 (2)

C1—C2	1.364 (4)	C13—H13	0.9300
C1—C6	1.365 (4)	C14—N1	1.450 (4)
C1—Cl1	1.737 (3)	C14—C15	1.495 (4)
C2—C3	1.374 (4)	C14—H14A	0.9700
C2—H2	0.9300	C14—H14B	0.9700
C3—C4	1.372 (4)	C15—Cl2	1.779 (3)
C3—H3	0.9300	C15—H15A	0.9700
C4—C5	1.392 (4)	C15—H15B	0.9700
C4—C7	1.524 (4)	C16—N1	1.466 (3)
C5—C6	1.384 (4)	C16—C17	1.525 (4)
C5—H5	0.9300	C16—H16A	0.9700
C6—H6	0.9300	C16—H16B	0.9700
C7—N1	1.475 (3)	C17—N2	1.452 (4)
C7—C8	1.520 (4)	C17—H17A	0.9700
C7—H7	0.9800	C17—H17B	0.9700
C8—C13	1.375 (4)	C18—N3	1.307 (4)
C8—C9	1.382 (4)	C18—N2	1.350 (4)
C9—C10	1.368 (4)	C18—H18	0.9300
C9—H9	0.9300	C19—N3	1.353 (4)
C10—C11	1.376 (4)	C19—C20	1.355 (4)
C10—H10	0.9300	C19—N4	1.432 (4)
C11—C12	1.356 (4)	C20—N2	1.348 (4)
C11—H11	0.9300	C20—H20	0.9300
C12—C13	1.384 (4)	N4—O2	1.211 (4)
C12—H12	0.9300	N4—O1	1.225 (4)
C2—C1—C6	121.1 (3)	N1—C14—H14A	108.5
C2—C1—Cl1	119.2 (2)	C15—C14—H14A	108.5
C6—C1—Cl1	119.8 (2)	N1—C14—H14B	108.5
C1—C2—C3	119.0 (3)	C15—C14—H14B	108.5
C1—C2—H2	120.5	H14A—C14—H14B	107.5
C3—C2—H2	120.5	C14—C15—Cl2	111.8 (2)
C4—C3—C2	122.8 (3)	C14—C15—H15A	109.2
C4—C3—H3	118.6	Cl2—C15—H15A	109.2
C2—C3—H3	118.6	C14—C15—H15B	109.2
C3—C4—C5	116.5 (3)	Cl2—C15—H15B	109.2
C3—C4—C7	119.3 (2)	H15A—C15—H15B	107.9
C5—C4—C7	124.2 (2)	N1—C16—C17	112.0 (2)
C6—C5—C4	121.8 (3)	N1—C16—H16A	109.2
C6—C5—H5	119.1	C17—C16—H16A	109.2
C4—C5—H5	119.1	N1—C16—H16B	109.2
C1—C6—C5	118.9 (3)	C17—C16—H16B	109.2
C1—C6—H6	120.6	H16A—C16—H16B	107.9
C5—C6—H6	120.6	N2—C17—C16	111.8 (2)
N1—C7—C8	109.3 (2)	N2—C17—H17A	109.3
N1—C7—C4	115.8 (2)	C16—C17—H17A	109.3
C8—C7—C4	116.5 (2)	N2—C17—H17B	109.3
N1—C7—H7	104.6	C16—C17—H17B	109.3
C8—C7—H7	104.6	H17A—C17—H17B	107.9
C4—C7—H7	104.6	N3—C18—N2	113.2 (3)
C13—C8—C9	117.5 (3)	N3—C18—H18	123.4
C13—C8—C7	124.7 (3)	N2—C18—H18	123.4
C9—C8—C7	117.8 (2)	N3—C19—C20	112.3 (3)
C10—C9—C8	121.7 (3)	N3—C19—N4	121.4 (3)
C10—C9—H9	119.2	C20—C19—N4	126.2 (3)
C8—C9—H9	119.2	N2—C20—C19	105.0 (3)
C9—C10—C11	119.8 (3)	N2—C20—H20	127.5
C9—C10—H10	120.1	C19—C20—H20	127.5
C11—C10—H10	120.1	C14—N1—C16	112.7 (2)
C12—C11—C10	119.7 (3)	C14—N1—C7	113.5 (2)
C12—C11—H11	120.2	C16—N1—C7	115.5 (2)
C10—C11—H11	120.2	C20—N2—C18	106.5 (2)
C11—C12—C13	120.4 (3)	C20—N2—C17	126.7 (3)
C11—C12—H12	119.8	C18—N2—C17	126.8 (3)
C13—C12—H12	119.8	C18—N3—C19	103.0 (3)
C8—C13—C12	121.0 (3)	O2—N4—O1	125.0 (3)
C8—C13—H13	119.5	O2—N4—C19	116.4 (3)
C12—C13—H13	119.5	O1—N4—C19	118.5 (3)
N1—C14—C15	115.1 (2)
C6—C1—C2—C3	−0.6 (5)	N1—C14—C15—Cl2	−58.3 (3)
Cl1—C1—C2—C3	179.4 (2)	N1—C16—C17—N2	−70.4 (3)
C1—C2—C3—C4	−0.4 (5)	N3—C19—C20—N2	−0.3 (3)
C2—C3—C4—C5	1.3 (4)	N4—C19—C20—N2	−178.3 (3)
C2—C3—C4—C7	−177.3 (3)	C15—C14—N1—C16	156.5 (3)
C3—C4—C5—C6	−1.3 (4)	C15—C14—N1—C7	−69.7 (3)
C7—C4—C5—C6	177.2 (3)	C17—C16—N1—C14	−83.4 (3)
C2—C1—C6—C5	0.6 (5)	C17—C16—N1—C7	143.8 (2)
Cl1—C1—C6—C5	−179.4 (2)	C8—C7—N1—C14	163.5 (2)
C4—C5—C6—C1	0.4 (5)	C4—C7—N1—C14	−62.6 (3)
C3—C4—C7—N1	118.5 (3)	C8—C7—N1—C16	−64.1 (3)
C5—C4—C7—N1	−60.0 (3)	C4—C7—N1—C16	69.8 (3)
C3—C4—C7—C8	−110.9 (3)	C19—C20—N2—C18	0.6 (3)
C5—C4—C7—C8	70.6 (3)	C19—C20—N2—C17	179.6 (3)
N1—C7—C8—C13	121.7 (3)	N3—C18—N2—C20	−0.7 (3)
C4—C7—C8—C13	−11.9 (4)	N3—C18—N2—C17	−179.7 (3)
N1—C7—C8—C9	−59.8 (3)	C16—C17—N2—C20	−70.0 (4)
C4—C7—C8—C9	166.6 (2)	C16—C17—N2—C18	108.8 (3)
C13—C8—C9—C10	−1.6 (4)	N2—C18—N3—C19	0.4 (3)
C7—C8—C9—C10	179.7 (3)	C20—C19—N3—C18	−0.1 (3)
C8—C9—C10—C11	0.7 (4)	N4—C19—N3—C18	178.0 (3)
C9—C10—C11—C12	0.5 (5)	N3—C19—N4—O2	178.6 (3)
C10—C11—C12—C13	−0.9 (5)	C20—C19—N4—O2	−3.6 (5)
C9—C8—C13—C12	1.2 (4)	N3—C19—N4—O1	−2.0 (4)
C7—C8—C13—C12	179.8 (3)	C20—C19—N4—O1	175.8 (3)
C11—C12—C13—C8	0.0 (5)