Aqua­[N-(2-hydroxy-5-nitro­benzyl)­imino­diacetato-κ⁴O,N,O′,O′′]copper(II)

The structure of the title compound, [Cu(NO₂-XDAH)(H₂O)] [where NO₂-XDAH₃ is N-(2-hydroxy-5-nitro­benzyl)­imino­di­acetic acid, C₁₁H₁₀N₂O₇], shows that the mononuclear complex unit contains a CuNO₄ distorted square pyramid. The H atom attached to the phenolic O atom is retained, while the two carboxyl­ate groups are deprotonated in the complex.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.053
• wR factor = 0.086
• Data-to-parameter ratio = 11.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.63 Ratio
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O8     -   H8D    ...       1.01 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          3
            O8  -CU1 -N2  -C8   -106.60  1.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          7
            O8  -CU1 -N2  -C7    133.40  1.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         11
            O8  -CU1 -N2  -C10    15.00  1.20   1.555   1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   0 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
   1 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
   4 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1999); software used to prepare material for publication: SHELXTL/PC.

Aqua[N-(2-hydroxy-5-nitrobenzyl)iminodiacetato-κ⁴O,N,O',O'']copper(II)

Crystal data

[Cu(C11H10N2O7)(H2O)]	F(000) = 740
Mr = 363.77	Dx = 1.773 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.341 (11) Å	Cell parameters from 741 reflections
b = 7.400 (5) Å	θ = 3.1–21.1°
c = 12.149 (9) Å	µ = 1.65 mm^−1
β = 98.902 (11)°	T = 293 K
V = 1362.6 (17) Å^3	Plate, blue
Z = 4	0.20 × 0.20 × 0.02 mm

Data collection

Bruker SMART 1K CCD diffractometer	2399 independent reflections
Radiation source: fine-focus sealed tube	1536 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
φ and ω scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −17→18
Tmin = 0.734, Tmax = 0.968	k = −8→7
5397 measured reflections	l = −14→14

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 0.87	w = 1/[σ^2(Fo^2) + (0.0191P)^2] where P = (Fo^2 + 2Fc^2)/3
2399 reflections	(Δ/σ)max < 0.001
203 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.40 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
Cu1	0.61491 (4)	0.98206 (8)	0.45126 (5)	0.0319 (2)
N2	0.6894 (2)	0.7879 (5)	0.5353 (3)	0.0250 (10)
O3	0.7338 (2)	1.0734 (5)	0.3559 (3)	0.0430 (11)
O4	0.6507 (2)	1.1354 (4)	0.5784 (3)	0.0408 (10)
O6	0.5716 (2)	0.7909 (4)	0.3502 (2)	0.0365 (9)
O8	0.5293 (2)	1.1435 (4)	0.3676 (3)	0.0419 (10)
H8C	0.5284	1.2650	0.3819	0.050*
H8D	0.5013	1.1135	0.2888	0.050*
C1	0.9526 (3)	1.1266 (8)	0.5952 (4)	0.0391 (14)
C2	0.9027 (3)	0.9697 (7)	0.5901 (4)	0.0355 (13)
H2	0.9184	0.8769	0.6409	0.043*
C3	0.8289 (3)	0.9524 (6)	0.5081 (4)	0.0298 (13)
C4	0.8072 (3)	1.0952 (7)	0.4339 (4)	0.0338 (13)
C5	0.8585 (4)	1.2509 (7)	0.4408 (5)	0.0502 (16)
H5	0.8433	1.3452	0.3909	0.060*
C6	0.9323 (4)	1.2655 (7)	0.5220 (5)	0.0493 (16)
H6	0.9674	1.3685	0.5264	0.059*
C7	0.7767 (3)	0.7766 (6)	0.4964 (4)	0.0298 (13)
H7A	0.7675	0.7406	0.4187	0.036*
H7B	0.8116	0.6831	0.5385	0.036*
C8	0.6986 (3)	0.8452 (6)	0.6535 (4)	0.0347 (14)
H8A	0.7562	0.8091	0.6918	0.042*
H8B	0.6543	0.7844	0.6890	0.042*
C9	0.6882 (3)	1.0506 (7)	0.6648 (5)	0.0371 (14)
C10	0.6381 (3)	0.6163 (6)	0.5074 (4)	0.0306 (13)
H10B	0.6022	0.5912	0.5647	0.037*
H10A	0.6787	0.5163	0.5053	0.037*
C11	0.5789 (3)	0.6335 (7)	0.3946 (4)	0.0303 (13)
H3	0.722 (3)	1.176 (7)	0.313 (4)	0.07 (2)*
N1	1.0325 (3)	1.1420 (8)	0.6794 (4)	0.0538 (15)
O1	1.0444 (3)	1.0325 (7)	0.7564 (4)	0.0962 (19)
O2	1.0853 (2)	1.2635 (6)	0.6676 (3)	0.0622 (13)
O5	0.7153 (2)	1.1153 (5)	0.7576 (3)	0.0599 (12)
O7	0.5405 (2)	0.4990 (5)	0.3489 (3)	0.0461 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0331 (4)	0.0242 (4)	0.0352 (4)	0.0014 (3)	−0.0054 (3)	−0.0025 (3)
N2	0.023 (2)	0.026 (2)	0.024 (2)	0.0009 (19)	0.000 (2)	−0.0008 (19)
O3	0.041 (2)	0.046 (3)	0.037 (2)	−0.004 (2)	−0.0071 (19)	0.012 (2)
O4	0.046 (2)	0.030 (2)	0.043 (2)	0.0022 (18)	−0.004 (2)	−0.0054 (19)
O6	0.046 (2)	0.029 (2)	0.029 (2)	0.0018 (18)	−0.0118 (18)	−0.0009 (17)
O8	0.044 (2)	0.027 (2)	0.047 (2)	0.0049 (17)	−0.0196 (19)	−0.0017 (18)
C1	0.030 (3)	0.053 (4)	0.033 (3)	−0.009 (3)	0.000 (3)	−0.007 (3)
C2	0.031 (3)	0.044 (4)	0.031 (3)	−0.002 (3)	0.004 (3)	0.003 (3)
C3	0.029 (3)	0.035 (3)	0.025 (3)	−0.003 (2)	0.004 (2)	−0.001 (3)
C4	0.029 (3)	0.042 (4)	0.030 (3)	−0.003 (3)	0.006 (3)	0.003 (3)
C5	0.051 (4)	0.039 (4)	0.058 (4)	−0.009 (3)	−0.001 (3)	0.014 (3)
C6	0.043 (4)	0.041 (4)	0.064 (4)	−0.018 (3)	0.005 (3)	−0.001 (3)
C7	0.029 (3)	0.032 (3)	0.027 (3)	0.004 (2)	0.003 (3)	0.001 (2)
C8	0.033 (3)	0.041 (4)	0.029 (3)	0.001 (3)	0.004 (3)	−0.003 (3)
C9	0.034 (3)	0.044 (4)	0.034 (3)	−0.005 (3)	0.009 (3)	−0.008 (3)
C10	0.034 (3)	0.023 (3)	0.033 (3)	−0.004 (2)	−0.003 (3)	0.005 (3)
C11	0.028 (3)	0.027 (3)	0.036 (3)	0.003 (3)	0.004 (3)	−0.005 (3)
N1	0.032 (3)	0.080 (4)	0.048 (4)	−0.018 (3)	0.003 (3)	−0.019 (3)
O1	0.074 (3)	0.133 (5)	0.067 (3)	−0.036 (3)	−0.034 (3)	0.033 (3)
O2	0.038 (3)	0.086 (3)	0.063 (3)	−0.017 (2)	0.007 (2)	−0.024 (3)
O5	0.075 (3)	0.059 (3)	0.039 (2)	−0.001 (2)	−0.009 (2)	−0.024 (2)
O7	0.053 (2)	0.024 (2)	0.055 (2)	−0.0069 (19)	−0.0125 (19)	−0.005 (2)

Geometric parameters (Å, º)

Cu1—O6	1.923 (3)	C3—C4	1.396 (6)
Cu1—O4	1.927 (3)	C3—C7	1.522 (6)
Cu1—O8	1.942 (3)	C4—C5	1.390 (6)
Cu1—N2	2.013 (4)	C5—C6	1.386 (6)
Cu1—O3	2.404 (4)	C5—H5	0.930
N2—C8	1.483 (5)	C6—H6	0.930
N2—C7	1.492 (5)	C7—H7A	0.970
N2—C10	1.504 (5)	C7—H7B	0.970
O3—C4	1.364 (5)	C8—C9	1.536 (7)
O3—H3	0.93 (5)	C8—H8A	0.970
O4—C9	1.280 (5)	C8—H8B	0.970
O6—C11	1.281 (5)	C9—O5	1.236 (5)
O8—H8C	0.9166	C10—C11	1.527 (6)
O8—H8D	1.0114	C10—H10B	0.970
C1—C6	1.364 (7)	C10—H10A	0.970
C1—C2	1.386 (7)	C11—O7	1.244 (5)
C1—N1	1.474 (6)	N1—O1	1.230 (6)
C2—C3	1.394 (6)	N1—O2	1.233 (5)
C2—H2	0.930
O6—Cu1—O4	166.55 (15)	C5—C4—C3	120.8 (5)
O6—Cu1—O8	88.83 (14)	C6—C5—C4	120.0 (5)
O4—Cu1—O8	98.24 (15)	C6—C5—H5	120.0
O6—Cu1—N2	84.92 (15)	C4—C5—H5	120.0
O4—Cu1—N2	86.82 (15)	C1—C6—C5	119.0 (5)
O8—Cu1—N2	171.63 (15)	C1—C6—H6	120.5
O6—Cu1—O3	96.43 (14)	C5—C6—H6	120.5
O4—Cu1—O3	94.42 (14)	N2—C7—C3	114.0 (4)
O8—Cu1—O3	94.40 (15)	N2—C7—H7A	108.7
N2—Cu1—O3	91.83 (15)	C3—C7—H7A	108.7
C8—N2—C7	111.5 (4)	N2—C7—H7B	108.7
C8—N2—C10	115.4 (4)	C3—C7—H7B	108.7
C7—N2—C10	110.2 (4)	H7A—C7—H7B	107.6
C8—N2—Cu1	104.4 (3)	N2—C8—C9	112.0 (4)
C7—N2—Cu1	110.3 (3)	N2—C8—H8A	109.2
C10—N2—Cu1	104.6 (3)	C9—C8—H8A	109.2
C4—O3—Cu1	107.7 (3)	N2—C8—H8B	109.2
C4—O3—H3	111 (3)	C9—C8—H8B	109.2
Cu1—O3—H3	114 (3)	H8A—C8—H8B	107.9
C9—O4—Cu1	113.9 (3)	O5—C9—O4	127.1 (5)
C11—O6—Cu1	113.6 (3)	O5—C9—C8	116.1 (5)
Cu1—O8—H8C	122.2	O4—C9—C8	116.8 (5)
Cu1—O8—H8D	121.0	N2—C10—C11	110.4 (4)
H8C—O8—H8D	112.2	N2—C10—H10B	109.6
C6—C1—C2	122.2 (5)	C11—C10—H10B	109.6
C6—C1—N1	118.4 (5)	N2—C10—H10A	109.6
C2—C1—N1	119.3 (5)	C11—C10—H10A	109.6
C1—C2—C3	119.4 (5)	H10B—C10—H10A	108.1
C1—C2—H2	120.3	O7—C11—O6	122.3 (5)
C3—C2—H2	120.3	O7—C11—C10	120.6 (5)
C2—C3—C4	118.6 (5)	O6—C11—C10	117.0 (4)
C2—C3—C7	120.2 (4)	O1—N1—O2	123.1 (5)
C4—C3—C7	121.1 (4)	O1—N1—C1	119.1 (5)
O3—C4—C5	122.6 (5)	O2—N1—C1	117.8 (5)
O3—C4—C3	116.6 (5)
O6—Cu1—N2—C8	−148.5 (3)	C7—C3—C4—O3	4.3 (7)
O4—Cu1—N2—C8	20.9 (3)	C2—C3—C4—C5	0.6 (7)
O8—Cu1—N2—C8	−106.6 (10)	C7—C3—C4—C5	−175.8 (5)
O3—Cu1—N2—C8	115.2 (3)	O3—C4—C5—C6	179.9 (5)
O6—Cu1—N2—C7	91.6 (3)	C3—C4—C5—C6	0.1 (8)
O4—Cu1—N2—C7	−99.1 (3)	C2—C1—C6—C5	1.1 (9)
O8—Cu1—N2—C7	133.4 (10)	N1—C1—C6—C5	178.5 (5)
O3—Cu1—N2—C7	−4.7 (3)	C4—C5—C6—C1	−0.9 (8)
O6—Cu1—N2—C10	−26.9 (3)	C8—N2—C7—C3	−57.6 (5)
O4—Cu1—N2—C10	142.5 (3)	C10—N2—C7—C3	172.9 (4)
O8—Cu1—N2—C10	15.0 (12)	Cu1—N2—C7—C3	57.9 (4)
O3—Cu1—N2—C10	−123.2 (3)	C2—C3—C7—N2	107.3 (5)
O6—Cu1—O3—C4	−134.5 (3)	C4—C3—C7—N2	−76.3 (6)
O4—Cu1—O3—C4	37.6 (3)	C7—N2—C8—C9	93.8 (5)
O8—Cu1—O3—C4	136.2 (3)	C10—N2—C8—C9	−139.4 (4)
N2—Cu1—O3—C4	−49.4 (3)	Cu1—N2—C8—C9	−25.2 (5)
O6—Cu1—O4—C9	39.5 (8)	Cu1—O4—C9—O5	−178.1 (4)
O8—Cu1—O4—C9	160.6 (3)	Cu1—O4—C9—C8	0.2 (6)
N2—Cu1—O4—C9	−12.7 (3)	N2—C8—C9—O5	−163.3 (4)
O3—Cu1—O4—C9	−104.3 (3)	N2—C8—C9—O4	18.2 (6)
O4—Cu1—O6—C11	−28.2 (8)	C8—N2—C10—C11	140.1 (4)
O8—Cu1—O6—C11	−150.3 (3)	C7—N2—C10—C11	−92.5 (4)
N2—Cu1—O6—C11	24.1 (3)	Cu1—N2—C10—C11	26.0 (4)
O3—Cu1—O6—C11	115.4 (3)	Cu1—O6—C11—O7	166.6 (4)
C6—C1—C2—C3	−0.4 (8)	Cu1—O6—C11—C10	−13.8 (5)
N1—C1—C2—C3	−177.8 (4)	N2—C10—C11—O7	169.9 (4)
C1—C2—C3—C4	−0.4 (7)	N2—C10—C11—O6	−9.7 (6)
C1—C2—C3—C7	176.0 (5)	C6—C1—N1—O1	168.7 (6)
Cu1—O3—C4—C5	−129.0 (5)	C2—C1—N1—O1	−13.8 (8)
Cu1—O3—C4—C3	50.9 (5)	C6—C1—N1—O2	−12.6 (7)
C2—C3—C4—O3	−179.3 (4)	C2—C1—N1—O2	164.9 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O5^i	0.93 (5)	1.68 (5)	2.590 (5)	168 (5)
O8—H8D···O7^ii	1.01	1.90	2.887 (5)	166
O8—H8C···O7^iii	0.92	1.79	2.648 (5)	154

Symmetry codes: (i) x, −y+5/2, z−1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) x, y+1, z.