Aqua­(N,N'-ethane-1,2-diylbis{N-[(3-nitro­phen­yl)meth­yl]glycinato})copper(II)

In the title complex, [Cu(C₂₀H₂₀N₄O₈)(H₂O)], the Cu atom has a distorted trigonal-bipyramidal coordination environment defined by an N₂O₃ donor set; the Cu and water O atoms lie on a twofold axis. In the crystal structure, extensive hydrogen bonding links mol­ecules into a two-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.038
• wR factor = 0.117
• Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.95

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Aqua(N,N'-ethane-1,2-diylbis{N-[(3-nitrophenyl)methyl]glycinato})copper(II)

Crystal data

[Cu(C20H20N4O8)(H2O)]	F(000) = 1084
Mr = 525.96	Dx = 1.610 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3689 reflections
a = 11.5227 (11) Å	θ = 2.9–26.6°
b = 9.1244 (9) Å	µ = 1.07 mm^−1
c = 20.782 (2) Å	T = 298 K
β = 96.757 (2)°	Prism, blue
V = 2169.8 (4) Å^3	0.23 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2360 independent reflections
Radiation source: fine-focus sealed tube	2090 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 27.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −14→14
Tmin = 0.769, Tmax = 0.850	k = −10→11
7022 measured reflections	l = −25→26

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0705P)^2 + 0.483P] where P = (Fo^2 + 2Fc^2)/3
2360 reflections	(Δ/σ)max < 0.001
161 parameters	Δρmax = 0.43 e Å^−3
4 restraints	Δρmin = −0.35 e Å^−3

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.5000	0.87101 (4)	0.7500	0.03389 (17)
C1	0.5163 (2)	0.9855 (3)	0.59852 (12)	0.0417 (5)
H1	0.4474	0.9910	0.6176	0.050*
C2	0.5658 (3)	1.1097 (3)	0.57657 (13)	0.0478 (6)
C3	0.6668 (3)	1.1077 (4)	0.54804 (17)	0.0645 (8)
H3	0.6984	1.1941	0.5340	0.077*
C4	0.7207 (3)	0.9755 (4)	0.54056 (18)	0.0734 (10)
H4	0.7898	0.9717	0.5216	0.088*
C5	0.6716 (3)	0.8483 (3)	0.56141 (15)	0.0566 (7)
H5	0.7071	0.7588	0.5549	0.068*
C6	0.5708 (2)	0.8512 (3)	0.59175 (12)	0.0416 (6)
C7	0.5227 (2)	0.7136 (3)	0.61848 (12)	0.0450 (6)
H7A	0.4381	0.7143	0.6094	0.054*
H7B	0.5515	0.6294	0.5967	0.054*
C8	0.4970 (2)	0.5668 (3)	0.71352 (14)	0.0471 (6)
H8A	0.5342	0.4789	0.6995	0.056*
H8B	0.4158	0.5654	0.6948	0.056*
C9	0.6844 (2)	0.6883 (3)	0.70654 (13)	0.0445 (6)
H9A	0.7221	0.7240	0.6703	0.053*
H9B	0.7059	0.5861	0.7132	0.053*
C10	0.72994 (18)	0.7743 (2)	0.76657 (12)	0.0351 (5)
N1	0.5062 (3)	1.2512 (3)	0.58254 (12)	0.0604 (6)
N2	0.55557 (15)	0.6980 (2)	0.68961 (10)	0.0366 (4)
O1	0.5441 (3)	1.3563 (3)	0.55522 (15)	0.0969 (10)
O2	0.4243 (2)	1.2557 (3)	0.61403 (13)	0.0753 (7)
O3	0.83175 (13)	0.7565 (2)	0.79004 (9)	0.0496 (5)
O4	0.66010 (13)	0.86543 (16)	0.78882 (10)	0.0418 (4)
O5	0.5000	1.0854 (2)	0.7500	0.0429 (6)
H5C	0.544 (5)	1.132 (2)	0.730 (3)	0.064*	0.50
H5D	0.5605 (6)	1.134 (2)	0.756 (3)	0.064*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0213 (2)	0.0195 (2)	0.0597 (3)	0.000	−0.00009 (16)	0.000
C1	0.0421 (13)	0.0417 (14)	0.0407 (13)	0.0029 (10)	0.0026 (10)	−0.0038 (10)
C2	0.0574 (16)	0.0438 (15)	0.0408 (14)	0.0021 (11)	0.0001 (11)	−0.0010 (11)
C3	0.066 (2)	0.061 (2)	0.068 (2)	−0.0084 (15)	0.0178 (16)	0.0110 (15)
C4	0.060 (2)	0.087 (3)	0.078 (2)	0.0019 (17)	0.0305 (17)	0.0059 (18)
C5	0.0556 (17)	0.0606 (18)	0.0558 (17)	0.0132 (13)	0.0153 (13)	−0.0053 (13)
C6	0.0432 (13)	0.0419 (14)	0.0385 (13)	0.0032 (10)	0.0001 (10)	−0.0073 (10)
C7	0.0460 (13)	0.0354 (13)	0.0515 (15)	0.0026 (10)	−0.0025 (11)	−0.0091 (11)
C8	0.0544 (15)	0.0211 (11)	0.0646 (16)	0.0014 (10)	0.0025 (12)	−0.0065 (11)
C9	0.0343 (12)	0.0470 (14)	0.0520 (15)	0.0132 (10)	0.0047 (10)	−0.0052 (11)
C10	0.0265 (10)	0.0248 (11)	0.0541 (14)	0.0016 (8)	0.0055 (9)	0.0028 (9)
N1	0.0856 (19)	0.0385 (13)	0.0533 (14)	0.0043 (12)	−0.0086 (13)	0.0024 (11)
N2	0.0324 (9)	0.0287 (10)	0.0479 (11)	0.0032 (7)	0.0017 (8)	−0.0046 (8)
O1	0.155 (3)	0.0468 (15)	0.091 (2)	−0.0008 (15)	0.0214 (19)	0.0129 (12)
O2	0.0714 (15)	0.0591 (14)	0.0938 (17)	0.0224 (11)	0.0035 (13)	−0.0042 (12)
O3	0.0261 (8)	0.0452 (10)	0.0757 (12)	0.0090 (7)	−0.0014 (7)	−0.0096 (9)
O4	0.0242 (8)	0.0295 (9)	0.0702 (12)	0.0031 (6)	−0.0003 (7)	−0.0111 (7)
O5	0.0301 (12)	0.0212 (11)	0.0797 (19)	0.000	0.0162 (12)	0.000

Geometric parameters (Å, º)

Cu1—O4^i	1.9252 (16)	C7—N2	1.489 (3)
Cu1—O4	1.9253 (16)	C7—H7A	0.9700
Cu1—O5	1.956 (2)	C7—H7B	0.9700
Cu1—N2^i	2.1601 (19)	C8—N2	1.488 (3)
Cu1—N2	2.1601 (18)	C8—C8^i	1.510 (6)
C1—C2	1.370 (4)	C8—H8A	0.9700
C1—C6	1.392 (3)	C8—H8B	0.9700
C1—H1	0.9300	C9—N2	1.487 (3)
C2—C3	1.367 (4)	C9—C10	1.515 (3)
C2—N1	1.475 (3)	C9—H9A	0.9700
C3—C4	1.373 (5)	C9—H9B	0.9700
C3—H3	0.9300	C10—O3	1.227 (3)
C4—C5	1.383 (5)	C10—O4	1.281 (3)
C4—H4	0.9300	N1—O2	1.211 (3)
C5—C6	1.386 (4)	N1—O1	1.221 (4)
C5—H5	0.9300	O5—H5C	0.818 (10)
C6—C7	1.505 (4)	O5—H5D	0.822 (10)
O4^i—Cu1—O4	176.97 (9)	N2—C7—H7B	109.1
O4^i—Cu1—O5	91.51 (4)	C6—C7—H7B	109.1
O4—Cu1—O5	91.52 (4)	H7A—C7—H7B	107.8
O4^i—Cu1—N2^i	83.64 (7)	N2—C8—C8^i	111.49 (17)
O4—Cu1—N2^i	94.14 (7)	N2—C8—H8A	109.3
O5—Cu1—N2^i	136.95 (5)	C8^i—C8—H8A	109.3
O4^i—Cu1—N2	94.14 (7)	N2—C8—H8B	109.3
O4—Cu1—N2	83.64 (7)	C8^i—C8—H8B	109.3
O5—Cu1—N2	136.95 (5)	H8A—C8—H8B	108.0
N2^i—Cu1—N2	86.09 (10)	N2—C9—C10	113.78 (18)
C2—C1—C6	118.9 (2)	N2—C9—H9A	108.8
C2—C1—H1	120.5	C10—C9—H9A	108.8
C6—C1—H1	120.5	N2—C9—H9B	108.8
C3—C2—C1	122.9 (3)	C10—C9—H9B	108.8
C3—C2—N1	118.5 (3)	H9A—C9—H9B	107.7
C1—C2—N1	118.7 (3)	O3—C10—O4	123.7 (2)
C2—C3—C4	118.7 (3)	O3—C10—C9	118.76 (19)
C2—C3—H3	120.7	O4—C10—C9	117.54 (19)
C4—C3—H3	120.7	O2—N1—O1	124.7 (3)
C3—C4—C5	119.7 (3)	O2—N1—C2	118.4 (3)
C3—C4—H4	120.2	O1—N1—C2	116.9 (3)
C5—C4—H4	120.2	C9—N2—C8	110.63 (19)
C4—C5—C6	121.4 (3)	C9—N2—C7	111.77 (18)
C4—C5—H5	119.3	C8—N2—C7	109.61 (19)
C6—C5—H5	119.3	C9—N2—Cu1	105.20 (14)
C5—C6—C1	118.4 (3)	C8—N2—Cu1	102.52 (14)
C5—C6—C7	121.1 (2)	C7—N2—Cu1	116.67 (14)
C1—C6—C7	120.5 (2)	C10—O4—Cu1	118.53 (15)
N2—C7—C6	112.59 (19)	Cu1—O5—H5C	121.7 (13)
N2—C7—H7A	109.1	Cu1—O5—H5D	122.4 (13)
C6—C7—H7A	109.1
C6—C1—C2—C3	0.1 (4)	C8^i—C8—N2—C7	−166.0 (2)
C6—C1—C2—N1	178.6 (2)	C8^i—C8—N2—Cu1	−41.4 (3)
C1—C2—C3—C4	0.5 (5)	C6—C7—N2—C9	−61.7 (3)
N1—C2—C3—C4	−178.0 (3)	C6—C7—N2—C8	175.2 (2)
C2—C3—C4—C5	0.5 (5)	C6—C7—N2—Cu1	59.4 (2)
C3—C4—C5—C6	−2.1 (5)	O4^i—Cu1—N2—C9	175.14 (15)
C4—C5—C6—C1	2.7 (4)	O4—Cu1—N2—C9	−6.93 (15)
C4—C5—C6—C7	−175.7 (3)	O5—Cu1—N2—C9	78.46 (16)
C2—C1—C6—C5	−1.7 (4)	N2^i—Cu1—N2—C9	−101.54 (16)
C2—C1—C6—C7	176.7 (2)	O4^i—Cu1—N2—C8	−69.12 (15)
C5—C6—C7—N2	98.9 (3)	O4—Cu1—N2—C8	108.81 (15)
C1—C6—C7—N2	−79.4 (3)	O5—Cu1—N2—C8	−165.80 (11)
N2—C9—C10—O3	169.5 (2)	N2^i—Cu1—N2—C8	14.20 (11)
N2—C9—C10—O4	−12.6 (3)	O4^i—Cu1—N2—C7	50.63 (16)
C3—C2—N1—O2	−171.9 (3)	O4—Cu1—N2—C7	−131.44 (17)
C1—C2—N1—O2	9.5 (4)	O5—Cu1—N2—C7	−46.05 (18)
C3—C2—N1—O1	7.7 (4)	N2^i—Cu1—N2—C7	133.95 (18)
C1—C2—N1—O1	−170.9 (3)	O3—C10—O4—Cu1	−175.94 (18)
C10—C9—N2—C8	−98.5 (2)	C9—C10—O4—Cu1	6.3 (3)
C10—C9—N2—C7	139.0 (2)	O5—Cu1—O4—C10	−136.46 (16)
C10—C9—N2—Cu1	11.5 (2)	N2^i—Cu1—O4—C10	86.24 (18)
C8^i—C8—N2—C9	70.3 (3)	N2—Cu1—O4—C10	0.65 (17)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O3^ii	0.97	2.54	3.457 (3)	157
C9—H9B···O4^ii	0.97	2.54	3.443 (3)	155
O5—H5C···O3^iii	0.82 (1)	1.91 (3)	2.696 (2)	161 (7)
O5—H5C···O3^iii	0.82 (1)	1.91 (3)	2.696 (2)	161 (7)

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