Poly[μ-azido-κ²N¹:N³-μ-2-(2-pyridylmethyl­amino)ethanesulfonato-κ⁴N,N′,O:O′-copper(II)]

In the title compound, [Cu(C₈H₁₁N₂O₃S)(N₃)]_n, the Cu^II center is six-coordinated by two N and two sulfonate O atoms from two different 2-(2-pyridylmethyl­amino)ethanesulfonate ligands together with two N atoms from two different azide anions in a distorted octa­hedral geometry. The azide anions act as μ-(1,3) bridges, giving rise to a two-dimensional coordination polymer parallel to the bc plane of the monoclinic unit cell.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.030
• wR factor = 0.080
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT411_ALERT_2_B Short Inter H...H Contact  H2B    ..  H2B     ..       1.97 Ang.

Alert level C
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.19 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.49 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         N1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.21

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2004); software used to prepare material for publication: SHELXTL.

Poly[µ-azido-κ⁴N¹:N³-µ-2-(2-pyridylmethylamino)ethanesulfonato- κ⁴N,N',O:O'-copper(II)]

Crystal data

[Cu(C8H11N2O3S)(N3)]	F(000) = 652
Mr = 320.81	Dx = 1.766 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3069 reflections
a = 11.4260 (13) Å	θ = 2.5–27.3°
b = 11.2920 (13) Å	µ = 2.00 mm^−1
c = 9.3237 (10) Å	T = 291 K
β = 91.239 (1)°	Block, dark-blue
V = 1202.7 (2) Å^3	0.33 × 0.17 × 0.11 mm
Z = 4

Data collection

Bruker APEX-II CCD area-detector diffractometer	2748 independent reflections
Radiation source: fine-focus sealed tube	2192 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.560, Tmax = 0.806	k = −14→14
10287 measured reflections	l = −12→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.04P)^2 + 0.3558P] where P = (Fo^2 + 2Fc^2)/3
2748 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.38 e Å^−3

Special details

Experimental. IR (KBr, ν, cm^-1): 773.7 [γ(C═C—H)], 758.1 (γ CH₂); 1226.8, 1177.6, 1048.6 (ν SO3^-); 1610.7, 1573.4 (ν C═C + C═ N); 2048.5 (νN₃^-); 3224.0 (v N—H).

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 (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.69156 (2)	0.44096 (2)	0.16419 (3)	0.03454 (11)
S1	0.41326 (5)	0.42576 (5)	0.17291 (6)	0.02931 (14)
O1	0.52924 (13)	0.38809 (13)	0.12036 (17)	0.0334 (4)
O2	0.37930 (16)	0.35852 (15)	0.29684 (18)	0.0436 (4)
O3	0.32683 (15)	0.42319 (15)	0.05598 (18)	0.0395 (4)
N1	0.75849 (19)	0.3092 (2)	0.0564 (3)	0.0563 (7)
N2	0.71672 (16)	0.23415 (17)	−0.0142 (2)	0.0342 (4)
N3	0.6801 (2)	0.1573 (2)	−0.0831 (3)	0.0552 (6)
N4	0.64604 (17)	0.59051 (16)	0.2671 (2)	0.0289 (4)
N5	0.85329 (17)	0.49761 (19)	0.2204 (2)	0.0414 (5)
C1	0.4312 (2)	0.57496 (19)	0.2268 (3)	0.0335 (5)
H1A	0.4466	0.6230	0.1430	0.040*
H1B	0.3589	0.6028	0.2676	0.040*
C2	0.5303 (2)	0.5916 (2)	0.3359 (3)	0.0336 (5)
H2A	0.5200	0.6663	0.3854	0.040*
H2B	0.5275	0.5286	0.4066	0.040*
C3	0.7395 (2)	0.6212 (2)	0.3730 (3)	0.0399 (6)
H3A	0.7247	0.5818	0.4633	0.048*
H3B	0.7394	0.7060	0.3898	0.048*
C4	0.8559 (2)	0.5841 (2)	0.3193 (3)	0.0418 (6)
C5	0.9546 (2)	0.4559 (3)	0.1703 (4)	0.0643 (9)
H5	0.9525	0.3957	0.1022	0.077*
C6	1.0611 (3)	0.4992 (4)	0.2163 (5)	0.0981 (15)
H6	1.1301	0.4692	0.1796	0.118*
C7	1.0641 (3)	0.5865 (4)	0.3161 (6)	0.1072 (17)
H7	1.1354	0.6166	0.3492	0.129*
C8	0.9610 (3)	0.6304 (3)	0.3683 (4)	0.0774 (11)
H8	0.9622	0.6908	0.4360	0.093*
H1N	0.647 (2)	0.650 (2)	0.196 (3)	0.037 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.02613 (16)	0.03147 (17)	0.0459 (2)	0.00212 (11)	−0.00282 (12)	−0.01355 (12)
S1	0.0277 (3)	0.0302 (3)	0.0301 (3)	−0.0020 (2)	0.0027 (2)	0.0012 (2)
O1	0.0296 (8)	0.0289 (8)	0.0419 (9)	−0.0012 (7)	0.0015 (7)	−0.0059 (7)
O2	0.0544 (11)	0.0398 (10)	0.0369 (9)	−0.0126 (8)	0.0094 (8)	0.0057 (8)
O3	0.0319 (9)	0.0479 (10)	0.0384 (9)	−0.0030 (7)	−0.0030 (7)	0.0008 (7)
N1	0.0343 (12)	0.0511 (14)	0.0830 (18)	0.0118 (10)	−0.0124 (11)	−0.0376 (13)
N2	0.0295 (10)	0.0312 (10)	0.0418 (11)	0.0067 (8)	−0.0002 (8)	−0.0032 (9)
N3	0.0633 (16)	0.0415 (13)	0.0606 (15)	−0.0019 (11)	−0.0077 (12)	−0.0152 (11)
N4	0.0317 (10)	0.0251 (9)	0.0301 (10)	−0.0005 (8)	0.0006 (8)	−0.0004 (8)
N5	0.0295 (11)	0.0412 (12)	0.0535 (13)	−0.0003 (9)	−0.0019 (9)	−0.0123 (10)
C1	0.0309 (12)	0.0300 (12)	0.0398 (13)	0.0045 (9)	0.0061 (10)	−0.0003 (9)
C2	0.0399 (13)	0.0279 (11)	0.0332 (12)	−0.0013 (10)	0.0076 (10)	−0.0036 (9)
C3	0.0435 (14)	0.0319 (12)	0.0440 (14)	−0.0015 (11)	−0.0070 (11)	−0.0101 (10)
C4	0.0395 (14)	0.0363 (13)	0.0492 (15)	−0.0051 (11)	−0.0069 (11)	−0.0066 (11)
C5	0.0293 (15)	0.074 (2)	0.089 (2)	0.0017 (14)	−0.0009 (15)	−0.0353 (18)
C6	0.0311 (17)	0.121 (4)	0.142 (4)	−0.003 (2)	0.002 (2)	−0.063 (3)
C7	0.0360 (18)	0.132 (4)	0.153 (4)	−0.022 (2)	−0.007 (2)	−0.071 (3)
C8	0.0500 (19)	0.077 (2)	0.105 (3)	−0.0147 (17)	−0.0103 (18)	−0.044 (2)

Geometric parameters (Å, º)

Cu1—N1	1.960 (2)	C1—C2	1.517 (3)
Cu1—O1	1.9826 (15)	C1—H1A	0.9700
Cu1—N5	2.014 (2)	C1—H1B	0.9700
Cu1—N4	2.0160 (18)	C2—H2A	0.9700
Cu1—O3^i	2.568 (2)	C2—H2B	0.9700
Cu1—N3^ii	2.610 (3)	C3—C4	1.492 (4)
S1—O2	1.4428 (17)	C3—H3A	0.9700
S1—O3	1.4554 (17)	C3—H3B	0.9700
S1—O1	1.4849 (16)	C4—C8	1.378 (4)
S1—C1	1.769 (2)	C5—C6	1.371 (4)
N1—N2	1.169 (3)	C5—H5	0.9300
N2—N3	1.153 (3)	C6—C7	1.356 (5)
N4—C3	1.479 (3)	C6—H6	0.9300
N4—C2	1.483 (3)	C7—C8	1.376 (5)
N4—H1N	0.94 (3)	C7—H7	0.9300
N5—C4	1.342 (3)	C8—H8	0.9300
N5—C5	1.343 (3)
N1—Cu1—O1	92.26 (8)	H1A—C1—H1B	107.8
N1—Cu1—N5	90.49 (9)	N4—C2—C1	111.60 (19)
O1—Cu1—N5	176.57 (7)	N4—C2—H2A	109.3
N1—Cu1—N4	170.89 (9)	C1—C2—H2A	109.3
O1—Cu1—N4	95.77 (7)	N4—C2—H2B	109.3
N5—Cu1—N4	81.65 (8)	C1—C2—H2B	109.3
O2—S1—O3	113.55 (11)	H2A—C2—H2B	108.0
O2—S1—O1	111.77 (10)	N4—C3—C4	110.3 (2)
O3—S1—O1	110.06 (10)	N4—C3—H3A	109.6
O2—S1—C1	107.79 (11)	C4—C3—H3A	109.6
O3—S1—C1	107.72 (11)	N4—C3—H3B	109.6
O1—S1—C1	105.52 (10)	C4—C3—H3B	109.6
S1—O1—Cu1	133.10 (10)	H3A—C3—H3B	108.1
N2—N1—Cu1	132.86 (18)	N5—C4—C8	120.7 (3)
N3—N2—N1	177.0 (2)	N5—C4—C3	115.3 (2)
C3—N4—C2	110.31 (19)	C8—C4—C3	124.0 (2)
C3—N4—Cu1	108.89 (14)	N5—C5—C6	122.1 (3)
C2—N4—Cu1	117.03 (14)	N5—C5—H5	118.9
C3—N4—H1N	106.3 (15)	C6—C5—H5	118.9
C2—N4—H1N	109.0 (15)	C7—C6—C5	118.9 (3)
Cu1—N4—H1N	104.7 (15)	C7—C6—H6	120.6
C4—N5—C5	119.2 (2)	C5—C6—H6	120.6
C4—N5—Cu1	114.61 (17)	C6—C7—C8	119.7 (3)
C5—N5—Cu1	126.22 (19)	C6—C7—H7	120.2
C2—C1—S1	112.86 (16)	C8—C7—H7	120.2
C2—C1—H1A	109.0	C7—C8—C4	119.5 (3)
S1—C1—H1A	109.0	C7—C8—H8	120.3
C2—C1—H1B	109.0	C4—C8—H8	120.3
S1—C1—H1B	109.0
O2—S1—O1—Cu1	−90.56 (15)	C3—N4—C2—C1	173.19 (19)
O3—S1—O1—Cu1	142.30 (13)	Cu1—N4—C2—C1	−61.6 (2)
C1—S1—O1—Cu1	26.34 (16)	S1—C1—C2—N4	78.3 (2)
N1—Cu1—O1—S1	170.97 (15)	C2—N4—C3—C4	162.2 (2)
N4—Cu1—O1—S1	−13.34 (15)	Cu1—N4—C3—C4	32.5 (2)
O1—Cu1—N1—N2	4.6 (3)	C5—N5—C4—C8	0.5 (5)
N5—Cu1—N1—N2	−177.4 (3)	Cu1—N5—C4—C8	179.5 (3)
O1—Cu1—N4—C3	152.36 (16)	C5—N5—C4—C3	−177.6 (3)
N5—Cu1—N4—C3	−25.37 (16)	Cu1—N5—C4—C3	1.4 (3)
O1—Cu1—N4—C2	26.46 (16)	N4—C3—C4—N5	−22.8 (3)
N5—Cu1—N4—C2	−151.27 (17)	N4—C3—C4—C8	159.2 (3)
N1—Cu1—N5—C4	−170.7 (2)	C4—N5—C5—C6	−0.3 (6)
N4—Cu1—N5—C4	13.89 (19)	Cu1—N5—C5—C6	−179.2 (3)
N1—Cu1—N5—C5	8.2 (3)	N5—C5—C6—C7	0.3 (7)
N4—Cu1—N5—C5	−167.2 (3)	C5—C6—C7—C8	−0.5 (8)
O2—S1—C1—C2	64.24 (19)	C6—C7—C8—C4	0.6 (8)
O3—S1—C1—C2	−172.87 (16)	N5—C4—C8—C7	−0.7 (6)
O1—S1—C1—C2	−55.32 (19)	C3—C4—C8—C7	177.2 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1N···O3^i	0.94 (3)	2.52 (2)	3.039 (3)	115.3 (18)
N4—H1N···O2^iii	0.94 (3)	2.38 (2)	3.097 (3)	133.1 (19)

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