2-Chloro-N-[(4-chloro­phen­yl)(phen­yl)meth­yl]-N-[2-(4-nitro-1H-imidazol-1-yl)eth­yl]ethanamine

Wen-Tai Zhang; Cheng-He Zhou; Qing-Gang Ji

doi:10.1107/S160053681100256X

. 2011 Jan 26;67(Pt 2):o491. doi: 10.1107/S160053681100256X

2-Chloro-N-[(4-chlorophenyl)(phenyl)methyl]-N-[2-(4-nitro-1H-imidazol-1-yl)ethyl]ethanamine

Wen-Tai Zhang ^a, Cheng-He Zhou ^a,^*, Qing-Gang Ji ^a

PMCID: PMC3051753 PMID: 21523147

Abstract

In the title compound, C₂₀H₂₀Cl₂N₄O₂, the nitroimidazole ring makes dihedral angles of 17.00 (1) and 60.45 (11)° with the phenyl and chlorophenyl rings, respectively. The three-coordinate N atom connected to two methylene 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 _r = 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
Δρ_max = 0.49 e Å⁻³
Δρ_min = −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.

Supplementary Material

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

e-67-0o491-sup1.cif^{(20.8KB, cif)}

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

e-67-0o491-Isup2.hkl^{(169.2KB, hkl)}

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

Acknowledgments

We thank Southwest University (grant Nos. SWUB2006018 and XSGX0602), the Natural Science Foundation of Chongqing (grant No. 2009BB5296) and the Research Funds for the Central Universities (XDJK2009c092) for financial support.

supplementary crystallographic information

Comment

Nitrogen mustards as anticancer agents containing typical β-chloroethylamine moiety with easy synthesis and inexpensive expense are one of the most important antitumor drugs (Zhuang et al., 2008). Nitroimidazole compounds are also extensively used in the treatment of various cancers as clinical radiosensitizer (Cai et al., 2009). In view of this, it is of great interest for us to investigate the nitrogen mustard-based nitroimidazoles as new potential anticancer agents. Herein we would like to report the crystal structure of the title compound (I).

The title compound, C₂₀H₂₀Cl₂N₄O₂, crystallized in non-chiral monoclinic crystal system of P2(1)/n space group, including a racemic chiral isomers. In the molecule, the nitroimidazole ring makes dihedral angles of 17.00 (1) and 60.45 (11)°, respectively, with the benzene and chlorophenyl ring.

Experimental

The intermediate 2-chloro-N-(2-chloroethyl)-N-((4-chlorophenyl(phenyl)methyl)ethanamine (0.85 g, 2.5 mmol), which was prepared according to the procedure of Fang et al.(2010) and Gan et al.(2010), reacted with 4-nitroimidazole (0.34 g, 3.0 mmol) in the presence of weak base in acetonitrile at 60 °C for 12 h to produce the title compound (I) 0.30 g as white solid via silica gel column chromatography (ethyl acetate/petroleum ether, 1/2, V/V). A crystal of (I) suitable for X-ray analysis was grown from a mixture solution of ethyl acetate and petroleum ether by slow evaporation at room temperature.

Figures

Crystal data

C₂₀H₂₀Cl₂N₄O₂	Z = 4
M_r = 419.30	F(000) = 872
Monoclinic, P2₁/n	D_x = 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

Open in a new tab

Data collection

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

Open in a new tab

Refinement

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(F_o²) + (0.0576P)² + 0.904P] where P = (F_o² + 2F_c²)/3
3449 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Open in a new tab

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.

Open in a new tab

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

	x	y	z	U_iso*/U_eq
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)

Open in a new tab

Atomic displacement parameters (Å²)

	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)

Open in a new tab

Geometric parameters (Å, °)

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)

Open in a new tab

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5107).

References

Bruker (2000). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
Cai, J. L., Li, S., Zhou, C. H., Gan, L. L. & Wu, J. (2009). Chin J New Drugs, 18, 598–652.
Fang, B., Zhou, C. H. & Rao, X. C. (2010). Eur J Med Chem 45, 4388–4398. [DOI] [PubMed]
Gan, L. L., Fang, B. & Zhou, C. H. (2010). Bull Kor. Chem Soc 31, 3684–3693.
Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
Zhuang, Y. Y., Zhou, C. H., Wang, Y. F. & Li, D. H. (2008). Chin Pharm J 43, 1281–1287.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

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

e-67-0o491-sup1.cif^{(20.8KB, cif)}

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

e-67-0o491-Isup2.hkl^{(169.2KB, hkl)}

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

[bb1] Bruker (2000). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.

[bb2] Cai, J. L., Li, S., Zhou, C. H., Gan, L. L. & Wu, J. (2009). Chin J New Drugs, 18, 598–652.

[bb3] Fang, B., Zhou, C. H. & Rao, X. C. (2010). Eur J Med Chem 45, 4388–4398. [DOI] [PubMed]

[bb4] Gan, L. L., Fang, B. & Zhou, C. H. (2010). Bull Kor. Chem Soc 31, 3684–3693.

[bb5] Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.

[bb6] Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]

[bb7] Zhuang, Y. Y., Zhou, C. H., Wang, Y. F. & Li, D. H. (2008). Chin Pharm J 43, 1281–1287.

PERMALINK

2-Chloro-N-[(4-chlorophenyl)(phenyl)methyl]-N-[2-(4-nitro-1H-imidazol-1-yl)ethyl]ethanamine

Wen-Tai Zhang

Cheng-He Zhou

Qing-Gang Ji

Abstract

Related literature

Experimental

Crystal data

Data collection

Refinement

Supplementary Material

Acknowledgments

supplementary crystallographic information

Comment

Experimental

Refinement

Figures

Fig. 1.

Crystal data

Data collection

Refinement

Special details

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

Atomic displacement parameters (Å²)

Geometric parameters (Å, °)

Footnotes

References

Associated Data

Supplementary Materials

ACTIONS

PERMALINK

RESOURCES

Cite

Add to Collections

PERMALINK

2-Chloro-N-[(4-chloro­phen­yl)(phen­yl)meth­yl]-N-[2-(4-nitro-1H-imidazol-1-yl)eth­yl]ethanamine

Wen-Tai Zhang

Cheng-He Zhou

Qing-Gang Ji

Abstract

Related literature

Experimental

Crystal data

Data collection

Refinement

Supplementary Material

Acknowledgments

supplementary crystallographic information

Comment

Experimental

Refinement

Figures

Fig. 1.

Crystal data

Data collection

Refinement

Special details

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

Atomic displacement parameters (Å2)

Geometric parameters (Å, °)

Footnotes

References

Associated Data

Supplementary Materials

ACTIONS

PERMALINK

RESOURCES

Similar articles

Cited by other articles

Links to NCBI Databases

2-Chloro-N-[(4-chlorophenyl)(phenyl)methyl]-N-[2-(4-nitro-1H-imidazol-1-yl)ethyl]ethanamine

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

Atomic displacement parameters (Å²)