N-Methyl-4-nitro­anilinium chloride

Wang, J.-L.; Zhou, F.-R.; Wei, F.-Y.

doi:10.1107/S1600536812024117

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1973

doi:10.1107/S1600536812024117

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N-Methyl-4-nitroanilinium chloride

Jian-Long Wang,^a ^* Fu-Rong Zhou ^a and Fei-Yun Wei ^a

^aSchool of Chemical Engineering and Environment, North University of China, Taiyuan, People's Republic of China
^*Correspondence e-mail: wangjianlong@nuc.edu.cn

(Received 30 April 2012; accepted 26 May 2012; online 31 May 2012)

The asymmetric unit of the title salt, C₇H₉N₂O₂⁺·Cl⁻, contains two independent cations and anions. In the crystal, each N-methyl-4-nitroanilinium cation is linked to two Cl⁻ anions via N—H⋯Cl hydrogen bonds. π–π stacking is observed between the benzene rings of adjacent cations [centroid-to-centroid distances = 3.7684 (14) and 3.7917 (7) Å].

Related literature

For applications of N-methyl-4-nitrobenzenamine, see: Bellamy & Sammour (1993 ); Sammour (1994 ); Williams & Friedlander (2000 ); Davies & Provatas (2006 ).

Experimental

Crystal data

C₇H₉N₂O₂⁺·Cl⁻
M_r = 188.61
Monoclinic, P 2₁ /c
a = 7.0509 (14) Å
b = 19.120 (4) Å
c = 13.443 (3) Å
β = 95.20 (3)°
V = 1804.8 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.12 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.927, T_max = 0.955
17869 measured reflections
4282 independent reflections
3022 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.124
S = 1.03
4282 reflections
236 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯Cl2ⁱ	0.90 (1)	2.18 (1)	3.0702 (17)	170 (2)
N2—H2B⋯Cl1ⁱ	0.89 (1)	2.16 (1)	3.0482 (19)	173 (2)
N4—H4A⋯Cl2ⁱⁱ	0.90 (1)	2.15 (1)	3.0361 (18)	168 (2)
N4—H4B⋯Cl1	0.89 (1)	2.26 (1)	3.1157 (18)	163 (2)
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x, -y+1, -z+1.

Data collection: RAPID-AUTO (Rigaku, 2000 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2000 ); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812024117/xu5532sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812024117/xu5532Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812024117/xu5532Isup3.cml

checkCIF report

Comment top

As a stablizer, N-methyl-4-nitrobenzenamine is used in order to lengthen the useful service life of double-base and minimum smoke propellants (Bellamy & Sammour, 1993; Sammour, 1994; Williams & Friedlander, 2000). As a important ingredient, N-methyl-4-nitrobenzenamine can improve melt-cast explosive systems mechanical properties (Davies & Provatas, 2006). In order to research reaction properties, here we report the synthesis and the crystal structure of the title compound (Fig. 1).

The title compound consists of a N-(4-nitrophenyl)-methylammonium cation and a chloride anion. The hydrochloric acid deprotonated and the N-methyl-4-nitrobenzenamine accepts the proton to produce the protonated organic cation, namely N-(4-nitrophenyl)-methylammonium chloride. In the crystal structure, contains two cations and two anions. They are linked by N—H···Cl hydrogen bonds to form a three-dimensional complex network.

Related literature top

For applications of N-methyl-4-nitrobenzenamine, see: Bellamy & Sammour (1993); Sammour (1994); Williams & Friedlander (2000); Davies & Provatas (2006).

Experimental top

The title compound was synthesized by N-methyl-4-nitrobenzenamine and concentrated hydrochloric acid in acetone at room temperature. Single crystals suitable for X-ray diffraction were obtained by evaporation of a solution of the title compound in acetone at room temperature.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2000); cell refinement: RAPID-AUTO (Rigaku, 2000); data reduction: CrystalStructure (Rigaku/MSC, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound.
	Fig. 2. The packing of the title compound.

N-Methyl-4-nitroanilinium chloride top

Crystal data top

C₇H₉N₂O₂⁺·Cl⁻	F(000) = 784
M_r = 188.61	D_x = 1.388 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4042 reflections
a = 7.0509 (14) Å	θ = 2.6–27.9°
b = 19.120 (4) Å	µ = 0.39 mm⁻¹
c = 13.443 (3) Å	T = 293 K
β = 95.20 (3)°	Block, yellow
V = 1804.8 (6) Å³	0.20 × 0.20 × 0.12 mm
Z = 8

Data collection top

Rigaku Saturn diffractometer	4282 independent reflections
Radiation source: rotating anode	3022 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.051
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 2.6°
ω scans	h = −9→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −25→25
T_min = 0.927, T_max = 0.955	l = −17→12
17869 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.124	w = 1/[σ²(F_o²) + (0.0651P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
4282 reflections	Δρ_max = 0.24 e Å⁻³
236 parameters	Δρ_min = −0.27 e Å⁻³
4 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.073 (4)

Crystal data top

C₇H₉N₂O₂⁺·Cl⁻	V = 1804.8 (6) Å³
M_r = 188.61	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.0509 (14) Å	µ = 0.39 mm⁻¹
b = 19.120 (4) Å	T = 293 K
c = 13.443 (3) Å	0.20 × 0.20 × 0.12 mm
β = 95.20 (3)°

Data collection top

Rigaku Saturn diffractometer	4282 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3022 reflections with I > 2σ(I)
T_min = 0.927, T_max = 0.955	R_int = 0.051
17869 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	4 restraints
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.24 e Å⁻³
4282 reflections	Δρ_min = −0.27 e Å⁻³
236 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.5920 (3)	0.47358 (8)	0.82213 (13)	0.0978 (7)
O2	0.6814 (3)	0.46456 (9)	0.97433 (15)	0.1113 (9)
O3	0.2318 (3)	0.28345 (10)	1.09445 (12)	0.0814 (6)
O4	0.1062 (3)	0.20296 (9)	0.99778 (13)	0.0869 (6)
N1	0.6303 (3)	0.43952 (9)	0.89526 (14)	0.0532 (5)
N2	0.5910 (2)	0.14490 (8)	0.86838 (12)	0.0408 (4)
N3	0.1557 (2)	0.26321 (10)	1.01448 (14)	0.0542 (5)
N4	0.0461 (2)	0.45901 (8)	0.70054 (11)	0.0400 (4)
C1	0.5619 (3)	0.26091 (10)	0.79113 (13)	0.0405 (4)
H1	0.5343	0.2393	0.7295	0.049*
C2	0.5707 (3)	0.33269 (10)	0.79740 (13)	0.0414 (4)
H2	0.5485	0.3603	0.7406	0.050*
C3	0.6131 (2)	0.36260 (9)	0.88971 (14)	0.0394 (4)
C4	0.6468 (3)	0.32360 (10)	0.97592 (14)	0.0442 (5)
H4	0.6757	0.3453	1.0374	0.053*
C5	0.6365 (3)	0.25178 (10)	0.96866 (13)	0.0416 (4)
H5	0.6580	0.2242	1.0256	0.050*
C6	0.5942 (2)	0.22099 (9)	0.87655 (12)	0.0351 (4)
C7	0.4023 (3)	0.11454 (11)	0.83074 (18)	0.0602 (6)
H7A	0.3053	0.1324	0.8696	0.090*
H7B	0.4074	0.0645	0.8365	0.090*
H7C	0.3732	0.1272	0.7620	0.090*
C8	0.0468 (3)	0.33800 (9)	0.76075 (13)	0.0388 (4)
H8	0.0125	0.3233	0.6956	0.047*
C9	0.0732 (3)	0.28977 (9)	0.83732 (14)	0.0411 (4)
H9	0.0568	0.2422	0.8251	0.049*
C10	0.1243 (3)	0.31429 (10)	0.93243 (13)	0.0402 (4)
C11	0.1482 (3)	0.38398 (10)	0.95434 (14)	0.0474 (5)
H11	0.1817	0.3987	1.0195	0.057*
C12	0.1211 (3)	0.43201 (10)	0.87722 (13)	0.0423 (4)
H12	0.1360	0.4796	0.8898	0.051*
C13	0.0720 (2)	0.40829 (9)	0.78202 (12)	0.0347 (4)
C14	0.1958 (3)	0.45515 (11)	0.62862 (15)	0.0557 (6)
H14A	0.3184	0.4640	0.6634	0.084*
H14B	0.1701	0.4896	0.5772	0.084*
H14C	0.1948	0.4094	0.5991	0.084*
Cl1	0.10531 (8)	0.61298 (3)	0.77271 (4)	0.05256 (19)
Cl2	0.31979 (7)	0.57619 (3)	0.42629 (3)	0.04808 (18)
H2A	0.632 (3)	0.1249 (11)	0.9271 (10)	0.062 (7)*
H2B	0.684 (2)	0.1328 (12)	0.8311 (15)	0.075 (8)*
H4A	−0.0708 (18)	0.4519 (12)	0.6697 (15)	0.068 (7)*
H4B	0.041 (3)	0.5011 (7)	0.7277 (15)	0.064 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.187 (2)	0.0365 (10)	0.0681 (12)	−0.0036 (11)	0.0040 (12)	0.0119 (8)
O2	0.181 (2)	0.0497 (11)	0.0926 (13)	−0.0070 (12)	−0.0467 (15)	−0.0217 (10)
O3	0.1046 (14)	0.0890 (14)	0.0489 (10)	0.0101 (11)	−0.0028 (9)	0.0215 (9)
O4	0.1261 (17)	0.0515 (11)	0.0827 (12)	0.0016 (10)	0.0070 (11)	0.0284 (9)
N1	0.0590 (11)	0.0368 (10)	0.0633 (12)	−0.0019 (8)	0.0029 (9)	−0.0075 (9)
N2	0.0475 (10)	0.0353 (9)	0.0395 (9)	0.0044 (7)	0.0038 (7)	0.0004 (7)
N3	0.0558 (11)	0.0538 (12)	0.0544 (11)	0.0097 (9)	0.0121 (9)	0.0178 (9)
N4	0.0442 (9)	0.0350 (9)	0.0396 (9)	−0.0033 (7)	−0.0021 (7)	0.0040 (7)
C1	0.0491 (11)	0.0400 (11)	0.0317 (9)	−0.0016 (8)	0.0002 (8)	−0.0022 (7)
C2	0.0455 (11)	0.0402 (11)	0.0380 (10)	0.0005 (8)	0.0019 (8)	0.0049 (8)
C3	0.0381 (10)	0.0339 (10)	0.0463 (11)	−0.0009 (7)	0.0047 (8)	−0.0031 (8)
C4	0.0525 (12)	0.0453 (11)	0.0341 (10)	−0.0021 (9)	−0.0003 (8)	−0.0069 (8)
C5	0.0477 (11)	0.0428 (11)	0.0337 (9)	0.0026 (8)	0.0001 (8)	0.0035 (8)
C6	0.0331 (9)	0.0339 (9)	0.0381 (10)	0.0019 (7)	0.0026 (7)	−0.0008 (7)
C7	0.0611 (14)	0.0381 (12)	0.0789 (16)	−0.0080 (10)	−0.0066 (12)	−0.0052 (10)
C8	0.0414 (10)	0.0345 (10)	0.0400 (10)	−0.0010 (8)	0.0009 (8)	−0.0033 (8)
C9	0.0399 (10)	0.0312 (10)	0.0526 (12)	0.0011 (7)	0.0065 (8)	0.0024 (8)
C10	0.0398 (10)	0.0397 (11)	0.0416 (10)	0.0034 (8)	0.0067 (8)	0.0108 (8)
C11	0.0588 (13)	0.0462 (12)	0.0364 (10)	0.0007 (9)	−0.0010 (9)	0.0004 (8)
C12	0.0534 (12)	0.0314 (10)	0.0408 (10)	−0.0031 (8)	−0.0028 (8)	−0.0024 (8)
C13	0.0332 (9)	0.0340 (9)	0.0366 (9)	−0.0004 (7)	0.0015 (7)	0.0048 (7)
C14	0.0711 (15)	0.0500 (13)	0.0483 (12)	−0.0070 (10)	0.0177 (10)	0.0066 (10)
Cl1	0.0642 (4)	0.0381 (3)	0.0568 (3)	−0.0017 (2)	0.0129 (2)	0.0025 (2)
Cl2	0.0535 (3)	0.0514 (3)	0.0381 (3)	−0.0033 (2)	−0.0030 (2)	−0.0018 (2)

Geometric parameters (Å, º) top

O1—N1	1.190 (2)	C4—C5	1.378 (3)
O2—N1	1.191 (2)	C4—H4	0.9300
O3—N3	1.220 (2)	C5—C6	1.379 (2)
O4—N3	1.218 (2)	C5—H5	0.9300
N1—C3	1.477 (2)	C7—H7A	0.9600
N2—C6	1.459 (2)	C7—H7B	0.9600
N2—C7	1.497 (3)	C7—H7C	0.9600
N2—H2A	0.901 (9)	C8—C9	1.382 (2)
N2—H2B	0.891 (10)	C8—C13	1.382 (2)
N3—C10	1.475 (2)	C8—H8	0.9300
N4—C13	1.462 (2)	C9—C10	1.379 (3)
N4—C14	1.496 (3)	C9—H9	0.9300
N4—H4A	0.898 (10)	C10—C11	1.372 (3)
N4—H4B	0.885 (10)	C11—C12	1.385 (3)
C1—C2	1.376 (3)	C11—H11	0.9300
C1—C6	1.380 (2)	C12—C13	1.372 (2)
C1—H1	0.9300	C12—H12	0.9300
C2—C3	1.374 (2)	C14—H14A	0.9600
C2—H2	0.9300	C14—H14B	0.9600
C3—C4	1.380 (3)	C14—H14C	0.9600

O1—N1—O2	123.02 (19)	C5—C6—C1	121.13 (16)
O1—N1—C3	119.47 (17)	C5—C6—N2	119.60 (15)
O2—N1—C3	117.52 (18)	C1—C6—N2	119.23 (15)
C6—N2—C7	114.80 (14)	N2—C7—H7A	109.5
C6—N2—H2A	110.9 (14)	N2—C7—H7B	109.5
C7—N2—H2A	109.6 (14)	H7A—C7—H7B	109.5
C6—N2—H2B	107.1 (16)	N2—C7—H7C	109.5
C7—N2—H2B	112.7 (16)	H7A—C7—H7C	109.5
H2A—N2—H2B	101 (2)	H7B—C7—H7C	109.5
O4—N3—O3	123.90 (19)	C9—C8—C13	119.26 (16)
O4—N3—C10	117.86 (18)	C9—C8—H8	120.4
O3—N3—C10	118.23 (19)	C13—C8—H8	120.4
C13—N4—C14	113.82 (15)	C10—C9—C8	118.03 (17)
C13—N4—H4A	107.0 (14)	C10—C9—H9	121.0
C14—N4—H4A	111.5 (14)	C8—C9—H9	121.0
C13—N4—H4B	107.5 (14)	C11—C10—C9	123.10 (17)
C14—N4—H4B	111.6 (15)	C11—C10—N3	118.39 (17)
H4A—N4—H4B	104.9 (19)	C9—C10—N3	118.50 (17)
C2—C1—C6	119.82 (16)	C10—C11—C12	118.52 (17)
C2—C1—H1	120.1	C10—C11—H11	120.7
C6—C1—H1	120.1	C12—C11—H11	120.7
C3—C2—C1	118.37 (16)	C13—C12—C11	119.01 (17)
C3—C2—H2	120.8	C13—C12—H12	120.5
C1—C2—H2	120.8	C11—C12—H12	120.5
C2—C3—C4	122.68 (17)	C12—C13—C8	122.08 (16)
C2—C3—N1	118.04 (16)	C12—C13—N4	118.90 (16)
C4—C3—N1	119.23 (16)	C8—C13—N4	119.02 (15)
C5—C4—C3	118.36 (16)	N4—C14—H14A	109.5
C5—C4—H4	120.8	N4—C14—H14B	109.5
C3—C4—H4	120.8	H14A—C14—H14B	109.5
C4—C5—C6	119.64 (16)	N4—C14—H14C	109.5
C4—C5—H5	120.2	H14A—C14—H14C	109.5
C6—C5—H5	120.2	H14B—C14—H14C	109.5

C6—C1—C2—C3	0.4 (3)	C13—C8—C9—C10	−0.1 (3)
C1—C2—C3—C4	−0.1 (3)	C8—C9—C10—C11	0.7 (3)
C1—C2—C3—N1	177.47 (17)	C8—C9—C10—N3	−179.08 (16)
O1—N1—C3—C2	6.2 (3)	O4—N3—C10—C11	168.9 (2)
O2—N1—C3—C2	−174.3 (2)	O3—N3—C10—C11	−12.1 (3)
O1—N1—C3—C4	−176.2 (2)	O4—N3—C10—C9	−11.3 (3)
O2—N1—C3—C4	3.3 (3)	O3—N3—C10—C9	167.65 (18)
C2—C3—C4—C5	−0.3 (3)	C9—C10—C11—C12	−0.5 (3)
N1—C3—C4—C5	−177.77 (17)	N3—C10—C11—C12	179.22 (17)
C3—C4—C5—C6	0.3 (3)	C10—C11—C12—C13	−0.1 (3)
C4—C5—C6—C1	0.0 (3)	C11—C12—C13—C8	0.6 (3)
C4—C5—C6—N2	177.53 (17)	C11—C12—C13—N4	−179.17 (17)
C2—C1—C6—C5	−0.4 (3)	C9—C8—C13—C12	−0.5 (3)
C2—C1—C6—N2	−177.88 (17)	C9—C8—C13—N4	179.30 (16)
C7—N2—C6—C5	118.4 (2)	C14—N4—C13—C12	111.3 (2)
C7—N2—C6—C1	−64.1 (2)	C14—N4—C13—C8	−68.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl2ⁱ	0.90 (1)	2.18 (1)	3.0702 (17)	170 (2)
N2—H2B···Cl1ⁱ	0.89 (1)	2.16 (1)	3.0482 (19)	173 (2)
N4—H4A···Cl2ⁱⁱ	0.90 (1)	2.15 (1)	3.0361 (18)	168 (2)
N4—H4B···Cl1	0.89 (1)	2.26 (1)	3.1157 (18)	163 (2)

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₇H₉N₂O₂⁺·Cl⁻
M_r	188.61
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.0509 (14), 19.120 (4), 13.443 (3)
β (°)	95.20 (3)
V (Å³)	1804.8 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.20 × 0.20 × 0.12

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.927, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	17869, 4282, 3022
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.124, 1.03
No. of reflections	4282
No. of parameters	236
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.27

Computer programs: RAPID-AUTO (Rigaku, 2000), CrystalStructure (Rigaku/MSC, 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl2ⁱ	0.901 (9)	2.179 (10)	3.0702 (17)	170.3 (19)
N2—H2B···Cl1ⁱ	0.891 (10)	2.162 (10)	3.0482 (19)	173 (2)
N4—H4A···Cl2ⁱⁱ	0.898 (10)	2.151 (11)	3.0361 (18)	168 (2)
N4—H4B···Cl1	0.885 (10)	2.259 (12)	3.1157 (18)	163 (2)

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x, −y+1, −z+1.

Acknowledgements

The authors thank China North Industries Group Corporation for financial support.

References

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