Tetra-kis(μ-4-azido-benzoato-κO:O')bis-[(N,N-dimethyl-formamide-κO)copper(II)].

The binuclear title compound, [Cu(2)(C(7)H(4)N(3)O(2))(4)(C(3)H(7)NO)(2)], is a discrete metal-organic compound having a paddle-wheel-type structure. The Cu⋯Cu distance is 2.6366 (5) Å and an inversion center is located at the mid-point of this bond. The Cu(II) cation is coordinated by four carboxyl-ate O atoms from four 4-azido-benzoate ligands, and one O atom from a dimethyl-formamide mol-ecule, forming an overall distorted octahedral geometry when the Cu⋯Cu bond is also considered.

Related literature

For similar complexes displaying a paddle-wheel structure, see: Del Sesto et al. (2000 ▶); Li et al. (2011 ▶). For the synthesis of 4-azido­benzoic acid, see: Sato et al. (2010 ▶).

Experimental

Crystal data

[Cu2(C7H4N3O2)4(C3H7NO)2]

M = 921.80

Monoclinic,

a = 11.9209 (8) Å

b = 17.9387 (10) Å

c = 9.3680 (5) Å

β = 91.277 (5)°

V = 2002.8 (2) Å3

Z = 2

Mo Kα radiation

μ = 1.14 mm−1

T = 293 K

0.2 × 0.2 × 0.2 mm

Data collection

Rigaku Mercury70 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2002 ▶) T min = 0.805, T max = 0.805

12312 measured reflections

3496 independent reflections

3141 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.091

S = 1.02

3496 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrystalClear (Rigaku, 2002 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811050999/bh2402sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050999/bh2402Isup2.hkl

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

[Cu2(C7H4N3O2)4(C3H7NO)2]	F(000) = 940
Mr = 921.80	Dx = 1.529 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4783 reflections
a = 11.9209 (8) Å	θ = 3.1–25°
b = 17.9387 (10) Å	µ = 1.14 mm−1
c = 9.3680 (5) Å	T = 293 K
β = 91.277 (5)°	Block, blue
V = 2002.8 (2) Å3	0.2 × 0.2 × 0.2 mm
Z = 2

Rigaku Mercury70 diffractometer	3496 independent reflections
Radiation source: fine-focus sealed tube	3141 reflections with I > 2σ(I)
graphite	Rint = 0.031
Detector resolution: 14.6306 pixels mm-1	θmax = 25.0°, θmin = 2.5°
ω scans	h = −14→14
Absorption correction: multi-scan (CrystalClear; Rigaku, 2002)	k = −19→21
Tmin = 0.805, Tmax = 0.805	l = −11→11
12312 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0482P)2 + 0.7327P] where P = (Fo2 + 2Fc2)/3
3496 reflections	(Δ/σ)max = 0.001
271 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.31 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
Cu1	0.05068 (2)	0.451211 (14)	0.58459 (3)	0.03461 (12)
O1	0.16267 (14)	0.44589 (9)	0.43570 (18)	0.0472 (4)
O5	0.12483 (14)	0.36844 (9)	0.72800 (17)	0.0470 (4)
O3	0.04281 (13)	0.62087 (9)	0.52445 (18)	0.0461 (4)
O2	0.07599 (14)	0.52740 (10)	0.28944 (17)	0.0467 (4)
O4	0.12931 (15)	0.53807 (9)	0.66805 (19)	0.0497 (4)
N7	0.1214 (2)	0.31119 (12)	0.9451 (2)	0.0567 (6)
N1	0.4690 (2)	0.4056 (2)	−0.1016 (3)	0.0854 (9)
N2	0.4467 (3)	0.4246 (2)	−0.2269 (4)	0.1045 (11)
N6	0.4782 (4)	0.8193 (3)	1.0817 (4)	0.1397 (18)
N3	0.4367 (4)	0.4395 (3)	−0.3436 (4)	0.155 (2)
N4	0.3389 (3)	0.84292 (18)	0.9011 (3)	0.0855 (9)
N5	0.4106 (3)	0.8267 (2)	0.9946 (3)	0.0987 (12)
C4	0.3881 (2)	0.42884 (18)	−0.0005 (3)	0.0584 (7)
C7	0.15287 (19)	0.48163 (13)	0.3208 (2)	0.0398 (5)
C15	0.0863 (2)	0.35912 (14)	0.8475 (3)	0.0484 (6)
H15A	0.0259	0.3892	0.8714	0.058*
C1	0.2378 (2)	0.46654 (13)	0.2094 (3)	0.0414 (5)
C8	0.17273 (19)	0.66528 (13)	0.6976 (2)	0.0409 (5)
C2	0.2172 (2)	0.48554 (14)	0.0677 (2)	0.0460 (6)
H2A	0.1524	0.5118	0.0430	0.055*
C6	0.3359 (2)	0.42912 (18)	0.2440 (3)	0.0595 (7)
H6A	0.3512	0.4159	0.3384	0.071*
C13	0.1512 (2)	0.73877 (15)	0.6624 (3)	0.0539 (6)
H13A	0.0985	0.7498	0.5907	0.065*
C3	0.2911 (2)	0.46609 (15)	−0.0371 (3)	0.0512 (6)
H3A	0.2753	0.4781	−0.1320	0.061*
C9	0.2511 (2)	0.65078 (16)	0.8053 (3)	0.0556 (7)
H9A	0.2661	0.6016	0.8308	0.067*
C14	0.11051 (19)	0.60338 (13)	0.6237 (2)	0.0397 (5)
C10	0.3073 (2)	0.70738 (18)	0.8752 (3)	0.0603 (7)
H10A	0.3596	0.6966	0.9475	0.072*
C12	0.2067 (3)	0.79604 (16)	0.7321 (3)	0.0635 (8)
H12B	0.1908	0.8453	0.7081	0.076*
C11	0.2856 (2)	0.78027 (17)	0.8373 (3)	0.0576 (7)
C17	0.0706 (3)	0.3082 (2)	1.0850 (3)	0.0822 (11)
H17A	0.0097	0.3432	1.0881	0.123*
H17B	0.1258	0.3207	1.1572	0.123*
H17C	0.0428	0.2588	1.1018	0.123*
C16	0.2150 (3)	0.26297 (19)	0.9201 (4)	0.0807 (10)
H16A	0.2407	0.2704	0.8248	0.121*
H16B	0.1923	0.2120	0.9315	0.121*
H16C	0.2746	0.2742	0.9873	0.121*
C5	0.4114 (2)	0.4111 (2)	0.1403 (3)	0.0717 (9)
H5A	0.4781	0.3871	0.1652	0.086*

	U11	U22	U33	U12	U13	U23
Cu1	0.04444 (19)	0.02783 (19)	0.03131 (18)	0.00240 (10)	−0.00460 (12)	0.00345 (10)
O1	0.0503 (10)	0.0503 (11)	0.0409 (9)	0.0099 (7)	0.0020 (7)	0.0104 (8)
O5	0.0606 (10)	0.0393 (10)	0.0408 (9)	0.0062 (8)	−0.0076 (7)	0.0085 (8)
O3	0.0538 (10)	0.0364 (10)	0.0474 (9)	−0.0021 (7)	−0.0126 (8)	0.0021 (8)
O2	0.0541 (10)	0.0447 (10)	0.0416 (9)	0.0133 (8)	0.0052 (7)	0.0058 (8)
O4	0.0648 (11)	0.0328 (10)	0.0507 (10)	−0.0040 (8)	−0.0167 (8)	0.0013 (8)
N7	0.0779 (15)	0.0430 (13)	0.0485 (12)	−0.0044 (11)	−0.0166 (11)	0.0141 (10)
N1	0.0804 (18)	0.112 (3)	0.0643 (18)	0.0276 (17)	0.0221 (14)	−0.0009 (17)
N2	0.088 (2)	0.157 (3)	0.069 (2)	0.035 (2)	0.0240 (17)	−0.016 (2)
N6	0.135 (3)	0.192 (5)	0.091 (3)	−0.087 (3)	−0.021 (2)	−0.024 (3)
N3	0.131 (3)	0.272 (7)	0.061 (2)	0.059 (3)	0.026 (2)	−0.009 (3)
N4	0.094 (2)	0.088 (2)	0.0738 (18)	−0.0434 (17)	0.0006 (16)	−0.0252 (16)
N5	0.105 (2)	0.124 (3)	0.0677 (19)	−0.068 (2)	0.0097 (18)	−0.0299 (19)
C4	0.0564 (16)	0.0638 (19)	0.0553 (16)	0.0072 (14)	0.0110 (13)	−0.0019 (14)
C7	0.0454 (13)	0.0319 (13)	0.0421 (13)	0.0001 (10)	−0.0022 (10)	−0.0011 (10)
C15	0.0594 (15)	0.0403 (15)	0.0450 (14)	−0.0014 (11)	−0.0108 (11)	0.0081 (11)
C1	0.0471 (13)	0.0353 (13)	0.0418 (13)	0.0009 (10)	0.0004 (10)	0.0003 (10)
C8	0.0455 (12)	0.0370 (13)	0.0403 (12)	−0.0018 (10)	0.0023 (10)	−0.0048 (10)
C2	0.0527 (14)	0.0416 (14)	0.0437 (13)	0.0080 (11)	−0.0016 (10)	0.0015 (11)
C6	0.0550 (16)	0.076 (2)	0.0476 (15)	0.0150 (14)	−0.0009 (12)	0.0108 (14)
C13	0.0583 (15)	0.0437 (16)	0.0593 (16)	0.0019 (12)	−0.0070 (12)	−0.0032 (13)
C3	0.0627 (16)	0.0511 (16)	0.0398 (14)	−0.0009 (13)	−0.0006 (11)	−0.0011 (12)
C9	0.0623 (16)	0.0483 (16)	0.0557 (16)	−0.0008 (13)	−0.0105 (12)	−0.0027 (13)
C14	0.0473 (13)	0.0348 (13)	0.0370 (12)	−0.0003 (10)	0.0025 (10)	−0.0008 (10)
C10	0.0559 (16)	0.073 (2)	0.0517 (16)	−0.0075 (14)	−0.0087 (12)	−0.0109 (15)
C12	0.0780 (19)	0.0398 (16)	0.0725 (19)	−0.0082 (14)	−0.0040 (15)	−0.0064 (14)
C11	0.0612 (16)	0.0577 (18)	0.0543 (16)	−0.0193 (14)	0.0113 (13)	−0.0180 (14)
C17	0.124 (3)	0.076 (2)	0.0466 (17)	−0.021 (2)	−0.0081 (17)	0.0223 (15)
C16	0.098 (2)	0.059 (2)	0.084 (2)	0.0146 (18)	−0.0344 (19)	0.0090 (18)
C5	0.0555 (17)	0.097 (3)	0.0628 (18)	0.0284 (16)	0.0050 (14)	0.0108 (18)

Cu1—O1	1.9545 (17)	C1—C2	1.387 (3)
Cu1—O4	1.9711 (17)	C1—C6	1.382 (4)
Cu1—O2i	1.9747 (16)	C8—C13	1.382 (4)
Cu1—O3i	1.9765 (16)	C8—C9	1.384 (3)
Cu1—O5	2.1767 (16)	C8—C14	1.496 (3)
Cu1—Cu1i	2.6363 (5)	C2—C3	1.379 (3)
O1—C7	1.256 (3)	C2—H2A	0.9300
O5—C15	1.231 (3)	C6—C5	1.377 (4)
O3—C14	1.258 (3)	C6—H6A	0.9300
O3—Cu1i	1.9765 (16)	C13—C12	1.379 (4)
O2—C7	1.260 (3)	C13—H13A	0.9300
O2—Cu1i	1.9747 (16)	C3—H3A	0.9300
O4—C14	1.261 (3)	C9—C10	1.375 (4)
N7—C15	1.316 (3)	C9—H9A	0.9300
N7—C16	1.436 (4)	C10—C11	1.378 (4)
N7—C17	1.456 (4)	C10—H10A	0.9300
N1—N2	1.245 (4)	C12—C11	1.376 (4)
N1—C4	1.429 (3)	C12—H12B	0.9300
N2—N3	1.130 (5)	C17—H17A	0.9600
N6—N5	1.142 (5)	C17—H17B	0.9600
N4—N5	1.245 (5)	C17—H17C	0.9600
N4—C11	1.417 (4)	C16—H16A	0.9600
C4—C3	1.373 (4)	C16—H16B	0.9600
C4—C5	1.379 (4)	C16—H16C	0.9600
C7—C1	1.495 (3)	C5—H5A	0.9300
C15—H15A	0.9300
O1—Cu1—O4	89.73 (8)	C3—C2—C1	121.1 (2)
O1—Cu1—O2i	168.40 (7)	C3—C2—H2A	119.4
O4—Cu1—O2i	88.43 (8)	C1—C2—H2A	119.4
O1—Cu1—O3i	89.17 (7)	C5—C6—C1	120.8 (3)
O4—Cu1—O3i	168.48 (7)	C5—C6—H6A	119.6
O2i—Cu1—O3i	90.35 (7)	C1—C6—H6A	119.6
O1—Cu1—O5	97.62 (6)	C12—C13—C8	120.9 (3)
O4—Cu1—O5	96.40 (7)	C12—C13—H13A	119.6
O2i—Cu1—O5	93.97 (7)	C8—C13—H13A	119.6
O3i—Cu1—O5	95.12 (7)	C4—C3—C2	119.6 (2)
O1—Cu1—Cu1i	85.10 (5)	C4—C3—H3A	120.2
O4—Cu1—Cu1i	85.48 (5)	C2—C3—H3A	120.2
O2i—Cu1—Cu1i	83.34 (5)	C10—C9—C8	121.5 (3)
O3i—Cu1—Cu1i	83.00 (5)	C10—C9—H9A	119.2
O5—Cu1—Cu1i	176.69 (5)	C8—C9—H9A	119.2
C7—O1—Cu1	122.33 (15)	O3—C14—O4	125.6 (2)
C15—O5—Cu1	119.94 (16)	O3—C14—C8	117.4 (2)
C14—O3—Cu1i	124.34 (15)	O4—C14—C8	117.0 (2)
C7—O2—Cu1i	123.31 (15)	C9—C10—C11	119.4 (3)
C14—O4—Cu1	121.62 (15)	C9—C10—H10A	120.3
C15—N7—C16	121.1 (3)	C11—C10—H10A	120.3
C15—N7—C17	121.1 (3)	C11—C12—C13	120.0 (3)
C16—N7—C17	117.7 (3)	C11—C12—H12B	120.0
N2—N1—C4	114.4 (3)	C13—C12—H12B	120.0
N3—N2—N1	173.3 (4)	C12—C11—C10	120.1 (3)
N5—N4—C11	114.0 (3)	C12—C11—N4	115.6 (3)
N6—N5—N4	173.3 (4)	C10—C11—N4	124.3 (3)
C3—C4—C5	120.1 (2)	N7—C17—H17A	109.5
C3—C4—N1	123.6 (3)	N7—C17—H17B	109.5
C5—C4—N1	116.2 (3)	H17A—C17—H17B	109.5
O1—C7—O2	125.8 (2)	N7—C17—H17C	109.5
O1—C7—C1	117.0 (2)	H17A—C17—H17C	109.5
O2—C7—C1	117.1 (2)	H17B—C17—H17C	109.5
O5—C15—N7	126.9 (3)	N7—C16—H16A	109.5
O5—C15—H15A	116.5	N7—C16—H16B	109.5
N7—C15—H15A	116.5	H16A—C16—H16B	109.5
C2—C1—C6	118.4 (2)	N7—C16—H16C	109.5
C2—C1—C7	121.0 (2)	H16A—C16—H16C	109.5
C6—C1—C7	120.5 (2)	H16B—C16—H16C	109.5
C13—C8—C9	118.2 (2)	C4—C5—C6	120.0 (3)
C13—C8—C14	120.7 (2)	C4—C5—H5A	120.0
C9—C8—C14	121.1 (2)	C6—C5—H5A	120.0