[1,2-Bis-(diisopropyl-phosphan-yl)ethane-κP,P']dichloridonickel(II)-9H-carbazole (1/2).

In the title compound, [NiCl(2)(C(14)H(32)P(2))]·2C(12)H(9)N, the neutral [Ni(dppe)Cl(2)] complex [dppe is 1,2-bis-(diisopropyl-phosphan-yl)ethane] consists of a tetracoordinated Ni(2+) cation and has a crystallographic twofold axis passing through the metal atom and the mid-point of the CH(2)-CH(2) bond of the dppe ligand. The metal atom shows slight tetra-hedral distortion from an ideal square-planar coordination geometry, as reflected in the dihedral angle between NiCl(2) and NiP(2) planes of 15.32 (2)°. The 9H-carbazole ring system is essentially planar (r.m.s. deviation = 0.022 Å). In the crystal packing, there are two symmetry-related 9H-carbazole mol-ecules between two adjacent Ni(II) complexes, with an angle between the carbazole mean planes of ca 77°.

Related literature

For the use of nickel complexes of the type [Ni(dppe)Cl2] as starting materials and precursors in metal-mediated and catalytic systems, respectively, see: Vicic & Jones (1997 ▶); Arévalo & García (2010 ▶). For details of tetra­hedral distortion and motifs, see: Angulo et al. (2003 ▶); Dahlenburg & Kurth (2001 ▶); Etter et al. (1990 ▶).

Experimental

Crystal data

[NiCl2(C14H32P2)]·2C12H9N

M = 726.35

Monoclinic,

a = 22.5830 (5) Å

b = 8.4374 (2) Å

c = 18.9630 (5) Å

β = 101.544 (2)°

V = 3540.15 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.82 mm−1

T = 122 K

0.42 × 0.16 × 0.02 mm

Data collection

Oxford Diffraction Xcalibur Atlas Gemini diffractometer

Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009 ▶); based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.851, T max = 0.987

12792 measured reflections

3484 independent reflections

2908 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.065

S = 1.05

3484 reflections

211 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.62 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811010555/bh2344sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010555/bh2344Isup2.hkl

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

[NiCl2(C14H32P2)]·2C12H9N	F(000) = 1536
Mr = 726.35	Dx = 1.363 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7654 reflections
a = 22.5830 (5) Å	θ = 3.3–26.0°
b = 8.4374 (2) Å	µ = 0.82 mm−1
c = 18.9630 (5) Å	T = 122 K
β = 101.544 (2)°	Prism, orange
V = 3540.15 (15) Å3	0.42 × 0.16 × 0.02 mm
Z = 4

Oxford Diffraction Xcalibur Atlas Gemini diffractometer	3484 independent reflections
Radiation source: fine-focus sealed tube	2908 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 10.4685 pixels mm-1	θmax = 26.1°, θmin = 3.5°
ω scans	h = −27→27
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009); based on expressions derived by Clark & Reid (1995)]	k = −10→10
Tmin = 0.851, Tmax = 0.987	l = −18→23
12792 measured reflections

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.065	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0343P)2 + 0.7966P] where P = (Fo2 + 2Fc2)/3
3484 reflections	(Δ/σ)max = 0.001
211 parameters	Δρmax = 0.62 e Å−3
0 restraints	Δρmin = −0.25 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
C1	0.13521 (7)	0.51654 (19)	0.17978 (9)	0.0162 (4)
C2	0.10421 (8)	0.4878 (2)	0.10949 (9)	0.0208 (4)
H2	0.0704	0.4185	0.0998	0.025*
C3	0.12477 (8)	0.5644 (2)	0.05455 (10)	0.0237 (4)
H3	0.1046	0.5469	0.0062	0.028*
C4	0.17440 (8)	0.6668 (2)	0.06818 (10)	0.0231 (4)
H4	0.1873	0.7177	0.0291	0.028*
C5	0.20488 (8)	0.6947 (2)	0.13744 (10)	0.0207 (4)
H5	0.2385	0.7648	0.1464	0.025*
C6	0.18570 (7)	0.61860 (19)	0.19446 (9)	0.0163 (4)
C7	0.20640 (7)	0.61872 (19)	0.27183 (9)	0.0164 (4)
C8	0.25374 (8)	0.6941 (2)	0.31818 (10)	0.0218 (4)
H8	0.2812	0.7597	0.2996	0.026*
C9	0.26007 (8)	0.6719 (2)	0.39150 (10)	0.0251 (4)
H9	0.2922	0.7226	0.4235	0.03*
C10	0.21966 (8)	0.5759 (2)	0.41916 (10)	0.0236 (4)
H10	0.2246	0.5635	0.4698	0.028*
C11	0.17264 (8)	0.4985 (2)	0.37428 (9)	0.0195 (4)
H11	0.1453	0.4334	0.3933	0.023*
C12	0.16687 (7)	0.51933 (19)	0.30049 (9)	0.0164 (4)
C13	0.12297 (7)	0.9420 (2)	0.35115 (9)	0.0193 (4)
H13	0.1382	0.8312	0.361	0.023*
C14	0.14981 (8)	1.0047 (2)	0.28869 (10)	0.0247 (4)
H14A	0.136	1.1137	0.2776	0.037*
H14B	0.1366	0.9377	0.2463	0.037*
H14C	0.194	1.0031	0.3022	0.037*
C15	0.14581 (8)	1.0381 (2)	0.41930 (10)	0.0247 (4)
H15A	0.19	1.0448	0.428	0.037*
H15B	0.1335	0.9862	0.4603	0.037*
H15C	0.1286	1.145	0.4134	0.037*
C16	0.01068 (8)	0.9163 (2)	0.40785 (9)	0.0213 (4)
H16	0.0272	1.0094	0.4381	0.026*
C17	0.03308 (9)	0.7674 (2)	0.45155 (11)	0.0316 (5)
H17A	0.0223	0.7741	0.499	0.047*
H17B	0.0771	0.7595	0.4573	0.047*
H17C	0.0141	0.6734	0.4262	0.047*
C18	−0.05797 (8)	0.9302 (2)	0.39410 (10)	0.0268 (4)
H18A	−0.0761	0.8401	0.3649	0.04*
H18B	−0.0705	1.0292	0.3684	0.04*
H18C	−0.0714	0.9301	0.4401	0.04*
C19	0.02934 (8)	0.7388 (2)	0.27707 (10)	0.0251 (4)
H19A	0.0633	0.7196	0.2523	0.03*
H19B	0.029	0.6525	0.3124	0.03*
Cl1	−0.025597 (18)	1.29303 (5)	0.16367 (2)	0.01865 (11)
N1	0.12485 (7)	0.45582 (17)	0.24411 (8)	0.0174 (3)
Ni1	0	1.11320 (3)	0.25	0.01164 (9)
P1	0.039792 (19)	0.93016 (5)	0.32401 (2)	0.01575 (11)
H1N	0.0953 (9)	0.405 (2)	0.2501 (10)	0.019*

	U11	U22	U33	U12	U13	U23
C1	0.0171 (8)	0.0132 (8)	0.0203 (9)	0.0045 (7)	0.0080 (7)	0.0006 (7)
C2	0.0194 (9)	0.0193 (9)	0.0239 (10)	−0.0008 (7)	0.0046 (8)	−0.0053 (7)
C3	0.0245 (10)	0.0283 (10)	0.0183 (10)	0.0045 (8)	0.0045 (8)	−0.0027 (8)
C4	0.0257 (10)	0.0252 (9)	0.0214 (10)	0.0059 (8)	0.0114 (8)	0.0056 (8)
C5	0.0188 (9)	0.0181 (9)	0.0272 (10)	0.0014 (7)	0.0091 (8)	0.0037 (8)
C6	0.0143 (8)	0.0140 (8)	0.0214 (9)	0.0033 (7)	0.0060 (7)	0.0007 (7)
C7	0.0149 (8)	0.0147 (8)	0.0205 (9)	0.0027 (7)	0.0054 (7)	0.0006 (7)
C8	0.0184 (9)	0.0204 (9)	0.0274 (10)	−0.0012 (8)	0.0061 (8)	0.0000 (8)
C9	0.0198 (9)	0.0280 (10)	0.0248 (10)	0.0000 (8)	−0.0016 (8)	−0.0049 (8)
C10	0.0268 (10)	0.0265 (10)	0.0169 (9)	0.0076 (8)	0.0029 (8)	0.0026 (7)
C11	0.0221 (9)	0.0161 (9)	0.0222 (10)	0.0029 (7)	0.0089 (8)	0.0036 (7)
C12	0.0172 (8)	0.0127 (8)	0.0198 (9)	0.0039 (7)	0.0047 (7)	−0.0006 (7)
C13	0.0157 (8)	0.0182 (9)	0.0218 (9)	0.0040 (7)	−0.0020 (7)	0.0012 (7)
C14	0.0183 (9)	0.0281 (10)	0.0274 (10)	0.0031 (8)	0.0037 (8)	0.0027 (8)
C15	0.0173 (9)	0.0268 (10)	0.0270 (10)	−0.0005 (8)	−0.0027 (8)	−0.0019 (8)
C16	0.0212 (9)	0.0252 (10)	0.0165 (9)	−0.0046 (8)	0.0013 (7)	0.0039 (7)
C17	0.0337 (11)	0.0314 (11)	0.0278 (11)	−0.0026 (9)	0.0016 (9)	0.0124 (9)
C18	0.0220 (9)	0.0363 (11)	0.0219 (10)	−0.0054 (8)	0.0042 (8)	0.0041 (8)
C19	0.0311 (10)	0.0137 (8)	0.0276 (10)	0.0010 (8)	−0.0014 (8)	−0.0001 (8)
Cl1	0.0204 (2)	0.0144 (2)	0.0208 (2)	0.00193 (16)	0.00338 (17)	0.00393 (16)
N1	0.0162 (7)	0.0158 (7)	0.0218 (8)	−0.0033 (6)	0.0074 (6)	−0.0011 (6)
Ni1	0.01075 (15)	0.00869 (15)	0.01507 (16)	0	0.00161 (11)	0
P1	0.0167 (2)	0.0120 (2)	0.0169 (2)	−0.00081 (17)	−0.00073 (17)	0.00090 (17)

C1—N1	1.386 (2)	C13—H13	1
C1—C2	1.397 (2)	C14—H14A	0.98
C1—C6	1.411 (2)	C14—H14B	0.98
C2—C3	1.383 (3)	C14—H14C	0.98
C2—H2	0.95	C15—H15A	0.98
C3—C4	1.398 (3)	C15—H15B	0.98
C3—H3	0.95	C15—H15C	0.98
C4—C5	1.376 (2)	C16—C18	1.524 (2)
C4—H4	0.95	C16—C17	1.534 (2)
C5—C6	1.399 (2)	C16—P1	1.8418 (18)
C5—H5	0.95	C16—H16	1
C6—C7	1.448 (2)	C17—H17A	0.98
C7—C8	1.394 (2)	C17—H17B	0.98
C7—C12	1.411 (2)	C17—H17C	0.98
C8—C9	1.382 (3)	C18—H18A	0.98
C8—H8	0.95	C18—H18B	0.98
C9—C10	1.399 (3)	C18—H18C	0.98
C9—H9	0.95	C19—C19i	1.505 (3)
C10—C11	1.384 (2)	C19—P1	1.8362 (18)
C10—H10	0.95	C19—H19A	0.99
C11—C12	1.390 (2)	C19—H19B	0.99
C11—H11	0.95	Ni1—Cl1	2.2221 (4)
C12—N1	1.387 (2)	N1—H1N	0.821 (19)
C13—C15	1.525 (2)	Ni1—P1i	2.1581 (5)
C13—C14	1.529 (3)	Ni1—P1	2.1581 (5)
C13—P1	1.8482 (17)	Ni1—Cl1i	2.2221 (4)
N1—C1—C2	129.44 (16)	H14B—C14—H14C	109.5
N1—C1—C6	108.91 (15)	C13—C15—H15A	109.5
C2—C1—C6	121.65 (16)	C13—C15—H15B	109.5
C3—C2—C1	117.26 (16)	H15A—C15—H15B	109.5
C3—C2—H2	121.4	C13—C15—H15C	109.5
C1—C2—H2	121.4	H15A—C15—H15C	109.5
C2—C3—C4	121.82 (17)	H15B—C15—H15C	109.5
C2—C3—H3	119.1	C18—C16—C17	111.69 (15)
C4—C3—H3	119.1	C18—C16—P1	111.96 (12)
C5—C4—C3	120.79 (17)	C17—C16—P1	112.49 (13)
C5—C4—H4	119.6	C18—C16—H16	106.8
C3—C4—H4	119.6	C17—C16—H16	106.8
C4—C5—C6	119.09 (17)	P1—C16—H16	106.8
C4—C5—H5	120.5	C16—C17—H17A	109.5
C6—C5—H5	120.5	C16—C17—H17B	109.5
C5—C6—C1	119.38 (16)	H17A—C17—H17B	109.5
C5—C6—C7	134.09 (16)	C16—C17—H17C	109.5
C1—C6—C7	106.53 (14)	H17A—C17—H17C	109.5
C8—C7—C12	119.53 (16)	H17B—C17—H17C	109.5
C8—C7—C6	133.67 (16)	C16—C18—H18A	109.5
C12—C7—C6	106.80 (14)	C16—C18—H18B	109.5
C9—C8—C7	118.98 (16)	H18A—C18—H18B	109.5
C9—C8—H8	120.5	C16—C18—H18C	109.5
C7—C8—H8	120.5	H18A—C18—H18C	109.5
C8—C9—C10	120.79 (17)	H18B—C18—H18C	109.5
C8—C9—H9	119.6	C19i—C19—P1	109.93 (8)
C10—C9—H9	119.6	C19i—C19—H19A	109.7
C11—C10—C9	121.37 (17)	P1—C19—H19A	109.7
C11—C10—H10	119.3	C19i—C19—H19B	109.7
C9—C10—H10	119.3	P1—C19—H19B	109.7
C10—C11—C12	117.70 (16)	H19A—C19—H19B	108.2
C10—C11—H11	121.1	C1—N1—C12	109.01 (14)
C12—C11—H11	121.1	C1—N1—H1N	126.9 (13)
N1—C12—C11	129.69 (15)	C12—N1—H1N	123.1 (13)
N1—C12—C7	108.71 (14)	P1i—Ni1—P1	88.61 (3)
C11—C12—C7	121.60 (16)	P1i—Ni1—Cl1i	168.757 (16)
C15—C13—C14	110.67 (15)	P1—Ni1—Cl1i	89.797 (16)
C15—C13—P1	114.66 (12)	P1i—Ni1—Cl1	89.797 (16)
C14—C13—P1	109.96 (12)	P1—Ni1—Cl1	168.758 (16)
C15—C13—H13	107.1	Cl1i—Ni1—Cl1	93.87 (2)
C14—C13—H13	107.1	C19—P1—C16	109.21 (9)
P1—C13—H13	107.1	C19—P1—C13	101.97 (8)
C13—C14—H14A	109.5	C16—P1—C13	106.35 (8)
C13—C14—H14B	109.5	C19—P1—Ni1	108.52 (6)
H14A—C14—H14B	109.5	C16—P1—Ni1	115.65 (6)
C13—C14—H14C	109.5	C13—P1—Ni1	114.22 (6)
H14A—C14—H14C	109.5
N1—C1—C2—C3	−179.52 (17)	C6—C1—N1—C12	1.32 (18)
C6—C1—C2—C3	−0.4 (3)	C11—C12—N1—C1	177.09 (17)
C1—C2—C3—C4	−0.1 (3)	C7—C12—N1—C1	−2.04 (18)
C2—C3—C4—C5	0.2 (3)	C19i—C19—P1—C16	93.81 (18)
C3—C4—C5—C6	0.3 (3)	C19i—C19—P1—C13	−153.95 (17)
C4—C5—C6—C1	−0.7 (2)	C19i—C19—P1—Ni1	−33.06 (19)
C4—C5—C6—C7	179.56 (17)	C18—C16—P1—C19	−79.07 (14)
N1—C1—C6—C5	−179.89 (15)	C17—C16—P1—C19	47.67 (15)
C2—C1—C6—C5	0.8 (2)	C18—C16—P1—C13	171.60 (13)
N1—C1—C6—C7	−0.11 (18)	C17—C16—P1—C13	−61.66 (14)
C2—C1—C6—C7	−179.40 (15)	C18—C16—P1—Ni1	43.64 (14)
C5—C6—C7—C8	−0.7 (3)	C17—C16—P1—Ni1	170.38 (11)
C1—C6—C7—C8	179.53 (18)	C15—C13—P1—C19	−151.39 (13)
C5—C6—C7—C12	178.62 (18)	C14—C13—P1—C19	83.17 (14)
C1—C6—C7—C12	−1.10 (18)	C15—C13—P1—C16	−37.02 (15)
C12—C7—C8—C9	−1.3 (2)	C14—C13—P1—C16	−162.46 (12)
C6—C7—C8—C9	178.01 (17)	C15—C13—P1—Ni1	91.77 (13)
C7—C8—C9—C10	−0.2 (3)	C14—C13—P1—Ni1	−33.67 (14)
C8—C9—C10—C11	0.8 (3)	P1i—Ni1—P1—C19	10.07 (6)
C9—C10—C11—C12	0.0 (3)	Cl1i—Ni1—P1—C19	178.94 (7)
C10—C11—C12—N1	179.44 (16)	Cl1—Ni1—P1—C19	−71.87 (12)
C10—C11—C12—C7	−1.5 (2)	P1i—Ni1—P1—C16	−113.00 (7)
C8—C7—C12—N1	−178.60 (15)	Cl1i—Ni1—P1—C16	55.87 (6)
C6—C7—C12—N1	1.93 (18)	Cl1—Ni1—P1—C16	165.06 (10)
C8—C7—C12—C11	2.2 (2)	P1i—Ni1—P1—C13	123.06 (7)
C6—C7—C12—C11	−177.29 (15)	Cl1i—Ni1—P1—C13	−68.07 (6)
C2—C1—N1—C12	−179.46 (16)	Cl1—Ni1—P1—C13	41.12 (12)

Ni1—Cl1	2.2221 (4)
Ni1—P1	2.1581 (5)

P1i—Ni1—P1	88.61 (3)
P1i—Ni1—Cl1i	168.757 (16)
P1i—Ni1—Cl1	89.797 (16)
Cl1i—Ni1—Cl1	93.87 (2)

Symmetry code: (i) .