Poly­[[[(2,2′-bi­pyridine)copper(II)]-hemi-μ₂-2-nitro­terephthalato-hemi-μ₄-2-nitro­terephthalato] monohydrate]

The polymeric title compound, {[Cu(C₈H₃NO₆)(C₁₀H₈N₂)]·H₂O}_n, has two disordered nitro­terephthalate units located around centres of inversion; one functions in a μ₂-bridging mode and the other in a μ₄-bridging mode to surround the five-coordinated Cu atom in a square-pyramidal geometry. The crystal structure reveals a two-dimensional hydrogen-bonded network involving a water mol­ecule of crystallization.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.052
• wR factor = 0.108
• Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT220_ALERT_2_A Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       4.66 Ratio

Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         O2

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.89 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C8
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Cu1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT301_ALERT_3_C Main Residue  Disorder .........................      10.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C12    -   C13    ...       1.38 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C13    -   C14_c  ...       1.37 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C16    -   C18    ...       1.39 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C17    -   C18_a  ...       1.38 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C15    -   C16    ...       1.53 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  13 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
  12 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Poly[[[(2,2'-bipyridine)copper(II)]-hemi(µ₂-2-nitroterephthalato)hemi(µ₄– 2-nitroterephthalato)] monohydrate]

Crystal data

[Cu(C8H3NO6)(C10H8N2)]·H2O	Z = 2
Mr = 446.85	F(000) = 454
Triclinic, P1	Dx = 1.618 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.537 (1) Å	Cell parameters from 963 reflections
b = 9.950 (1) Å	θ = 2.3–20.4°
c = 11.363 (1) Å	µ = 1.24 mm^−1
α = 94.156 (2)°	T = 295 K
β = 107.839 (2)°	Block, blue
γ = 113.535 (2)°	0.23 × 0.19 × 0.17 mm
V = 917.31 (16) Å^3

Data collection

Bruker APEX area-detector diffractometer	3534 independent reflections
Radiation source: fine-focus sealed tube	2227 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
φ and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −11→11
Tmin = 0.764, Tmax = 0.817	k = −12→12
5077 measured reflections	l = −14→11

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	w = 1/[σ^2(Fo^2) + (0.0309P)^2] where P = (Fo^2 + 2Fc^2)/3
3534 reflections	(Δ/σ)max = 0.001
295 parameters	Δρmax = 0.40 e Å^−3
29 restraints	Δρmin = −0.41 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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.49376 (7)	0.33223 (6)	0.52464 (5)	0.0378 (2)
O1	0.5543 (4)	0.4071 (4)	0.7055 (3)	0.0525 (9)
O2	0.3151 (6)	0.2287 (5)	0.6951 (4)	0.0899 (14)
O3	0.7700 (13)	0.3680 (13)	0.9325 (9)	0.124 (4)	0.50
O4	0.8944 (16)	0.6084 (18)	0.9832 (13)	0.174 (6)	0.50
O5	0.3408 (4)	0.4212 (3)	0.4883 (3)	0.0376 (8)
O6	0.1063 (4)	0.2104 (4)	0.3970 (4)	0.0772 (12)
O7	0.0193 (10)	0.3611 (9)	0.2169 (7)	0.082 (3)	0.50
O8	−0.2353 (10)	0.2929 (11)	0.1863 (7)	0.095 (3)	0.50
O1W	0.1511 (8)	0.0196 (7)	0.8189 (4)	0.135 (2)
H1W1	0.211 (7)	0.088 (6)	0.791 (6)	0.161*
H1W2	0.058 (4)	−0.035 (7)	0.761 (5)	0.161*
N1	0.6448 (5)	0.2354 (4)	0.5605 (4)	0.0453 (10)
N2	0.4367 (5)	0.2277 (4)	0.3480 (4)	0.0457 (11)
N3	0.7732 (13)	0.4851 (17)	0.9639 (11)	0.112 (5)	0.50
N4	−0.0966 (12)	0.3505 (10)	0.2492 (6)	0.055 (2)	0.50
C1	0.7537 (6)	0.2502 (6)	0.6743 (6)	0.0598 (15)
H1	0.7618	0.3100	0.7452	0.072*
C2	0.8528 (7)	0.1797 (7)	0.6887 (7)	0.0756 (19)
H2	0.9271	0.1915	0.7686	0.091*
C3	0.8426 (8)	0.0933 (7)	0.5872 (8)	0.084 (2)
H3	0.9083	0.0435	0.5968	0.100*
C4	0.7371 (8)	0.0790 (6)	0.4716 (7)	0.0711 (19)
H4	0.7324	0.0219	0.4007	0.085*
C5	0.6346 (6)	0.1498 (5)	0.4577 (5)	0.0482 (14)
C6	0.5173 (7)	0.1441 (5)	0.3380 (5)	0.0484 (13)
C7	0.4862 (9)	0.0596 (7)	0.2239 (6)	0.080 (2)
H7	0.5444	0.0047	0.2191	0.096*
C8	0.3671 (11)	0.0574 (8)	0.1161 (7)	0.108 (3)
H8	0.3405	−0.0024	0.0384	0.130*
C9	0.2889 (8)	0.1448 (7)	0.1258 (5)	0.082 (2)
H9	0.2113	0.1476	0.0540	0.099*
C10	0.3262 (7)	0.2286 (6)	0.2427 (5)	0.0572 (15)
H10	0.2726	0.2876	0.2483	0.069*
C11	0.4450 (8)	0.3425 (6)	0.7509 (5)	0.0537 (15)
C12	0.4756 (7)	0.4223 (6)	0.8818 (4)	0.0509 (14)
C13	0.6295 (7)	0.5016 (6)	0.9743 (5)	0.0568 (15)
H13	0.7196	0.5035	0.9574	0.068*	0.50
C14	0.3445 (7)	0.4221 (6)	0.9099 (5)	0.0586 (15)
H14	0.2383	0.3699	0.8500	0.070*
C15	0.1838 (6)	0.3429 (6)	0.4485 (5)	0.0429 (12)
C16	0.0913 (5)	0.4293 (5)	0.4740 (5)	0.0375 (11)
C17	0.1391 (5)	0.5109 (5)	0.5937 (5)	0.0423 (12)
H17	0.2323	0.5192	0.6580	0.051*
C18	−0.0489 (6)	0.4195 (5)	0.3816 (5)	0.0449 (13)
H18	−0.0832	0.3641	0.3002	0.054*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0397 (4)	0.0434 (4)	0.0398 (4)	0.0257 (3)	0.0182 (3)	0.0037 (3)
O1	0.055 (2)	0.071 (3)	0.043 (2)	0.038 (2)	0.0205 (19)	0.0063 (19)
O2	0.114 (4)	0.060 (3)	0.066 (3)	0.004 (3)	0.047 (3)	−0.010 (2)
O3	0.148 (8)	0.162 (8)	0.098 (7)	0.115 (7)	0.035 (5)	0.014 (6)
O4	0.124 (8)	0.228 (11)	0.183 (10)	0.083 (7)	0.080 (7)	−0.005 (7)
O5	0.0262 (18)	0.044 (2)	0.046 (2)	0.0189 (17)	0.0153 (15)	0.0051 (15)
O6	0.046 (2)	0.041 (2)	0.132 (3)	0.020 (2)	0.022 (2)	−0.009 (2)
O7	0.075 (6)	0.119 (7)	0.063 (5)	0.052 (6)	0.032 (5)	0.007 (5)
O8	0.052 (6)	0.148 (9)	0.063 (6)	0.053 (6)	−0.006 (4)	−0.025 (5)
O1W	0.134 (5)	0.109 (5)	0.073 (3)	−0.012 (4)	0.017 (3)	0.012 (3)
N1	0.041 (3)	0.041 (3)	0.063 (3)	0.021 (2)	0.026 (2)	0.014 (2)
N2	0.058 (3)	0.047 (3)	0.043 (3)	0.029 (2)	0.026 (2)	0.008 (2)
N3	0.163 (16)	0.128 (13)	0.054 (7)	0.091 (13)	0.021 (9)	0.001 (8)
N4	0.045 (6)	0.069 (7)	0.052 (6)	0.034 (6)	0.010 (5)	−0.002 (5)
C1	0.046 (4)	0.057 (4)	0.084 (4)	0.030 (3)	0.023 (3)	0.021 (3)
C2	0.047 (4)	0.075 (5)	0.119 (6)	0.040 (4)	0.027 (4)	0.041 (4)
C3	0.072 (5)	0.064 (5)	0.160 (8)	0.054 (4)	0.063 (5)	0.051 (5)
C4	0.072 (5)	0.056 (4)	0.126 (6)	0.044 (4)	0.066 (4)	0.033 (4)
C5	0.054 (4)	0.031 (3)	0.077 (4)	0.019 (3)	0.045 (3)	0.014 (3)
C6	0.057 (4)	0.041 (3)	0.057 (4)	0.021 (3)	0.037 (3)	0.007 (3)
C7	0.119 (6)	0.073 (5)	0.072 (5)	0.053 (5)	0.055 (4)	0.007 (4)
C8	0.193 (9)	0.085 (5)	0.064 (5)	0.066 (6)	0.067 (5)	0.000 (4)
C9	0.110 (6)	0.079 (5)	0.043 (4)	0.037 (5)	0.017 (4)	0.006 (3)
C10	0.070 (4)	0.057 (4)	0.042 (3)	0.027 (3)	0.019 (3)	0.002 (3)
C11	0.081 (5)	0.042 (3)	0.035 (3)	0.028 (4)	0.018 (3)	0.000 (3)
C12	0.077 (4)	0.044 (3)	0.033 (3)	0.026 (3)	0.022 (3)	0.004 (2)
C13	0.058 (4)	0.067 (4)	0.051 (4)	0.030 (4)	0.026 (3)	0.000 (3)
C14	0.054 (4)	0.070 (4)	0.038 (3)	0.019 (3)	0.013 (3)	−0.003 (3)
C15	0.043 (3)	0.039 (3)	0.053 (3)	0.023 (3)	0.020 (3)	0.009 (3)
C16	0.024 (3)	0.035 (3)	0.059 (3)	0.014 (2)	0.021 (2)	0.012 (2)
C17	0.025 (3)	0.049 (3)	0.057 (3)	0.020 (3)	0.014 (2)	0.015 (3)
C18	0.040 (3)	0.044 (3)	0.054 (3)	0.018 (3)	0.024 (3)	0.010 (3)

Geometric parameters (Å, º)

Cu1—O5	1.949 (3)	C4—C5	1.395 (6)
Cu1—O1	1.955 (3)	C4—H4	0.9300
Cu1—N1	1.994 (4)	C5—C6	1.453 (7)
Cu1—N2	1.996 (4)	C6—C7	1.372 (7)
Cu1—O5^i	2.373 (3)	C7—C8	1.384 (8)
O1—C11	1.268 (6)	C7—H7	0.9300
O2—C11	1.231 (6)	C8—C9	1.371 (8)
O3—N3	1.179 (13)	C8—H8	0.9300
O4—N3	1.250 (16)	C9—C10	1.378 (7)
O5—C15	1.287 (5)	C9—H9	0.9300
O5—Cu1^i	2.373 (3)	C10—H10	0.9300
O6—C15	1.213 (5)	C11—C12	1.518 (6)
O7—N4	1.236 (9)	C12—C13	1.375 (7)
O8—N4	1.160 (9)	C12—C14	1.381 (6)
O1W—H1W1	0.85 (6)	C13—C14^ii	1.370 (6)
O1W—H1W2	0.85 (5)	C13—H13	0.9300
N1—C1	1.341 (6)	C14—C13^ii	1.370 (6)
N1—C5	1.349 (6)	C14—H14	0.9300
N2—C10	1.333 (6)	C15—C16	1.525 (6)
N2—C6	1.359 (5)	C16—C17	1.372 (6)
C1—C2	1.365 (6)	C16—C18	1.386 (6)
C1—H1	0.9300	C17—C18^iii	1.376 (5)
C2—C3	1.341 (8)	C17—H17	0.9300
C2—H2	0.9300	C18—C17^iii	1.376 (5)
C3—C4	1.344 (8)	C18—H18	0.9300
C3—H3	0.9300
O5—Cu1—O1	88.80 (12)	N2—C6—C5	114.4 (4)
O5—Cu1—N1	178.37 (15)	C7—C6—C5	123.6 (5)
O1—Cu1—N1	91.64 (15)	C6—C7—C8	119.0 (6)
O5—Cu1—N2	98.57 (14)	C6—C7—H7	120.5
O1—Cu1—N2	170.92 (15)	C8—C7—H7	120.5
N1—Cu1—N2	80.84 (17)	C9—C8—C7	118.9 (6)
O5—Cu1—O5^i	77.27 (12)	C9—C8—H8	120.5
O1—Cu1—O5^i	89.05 (13)	C7—C8—H8	120.5
N1—Cu1—O5^i	104.30 (13)	C8—C9—C10	119.6 (6)
N2—Cu1—O5^i	97.70 (13)	C8—C9—H9	120.2
C11—O1—Cu1	115.6 (3)	C10—C9—H9	120.2
C15—O5—Cu1	123.1 (3)	N2—C10—C9	122.1 (5)
C15—O5—Cu1^i	131.6 (3)	N2—C10—H10	119.0
Cu1—O5—Cu1^i	102.73 (12)	C9—C10—H10	119.0
H1W1—O1W—H1W2	111 (6)	O2—C11—O1	125.6 (5)
C1—N1—C5	118.9 (4)	O2—C11—C12	118.8 (5)
C1—N1—Cu1	126.3 (4)	O1—C11—C12	115.4 (5)
C5—N1—Cu1	114.8 (3)	C13—C12—C14	117.1 (5)
C10—N2—C6	118.4 (4)	C13—C12—C11	123.5 (5)
C10—N2—Cu1	126.8 (3)	C14—C12—C11	119.3 (5)
C6—N2—Cu1	114.8 (3)	C14^ii—C13—C12	122.7 (5)
O3—N3—O4	123.4 (10)	C14^ii—C13—H13	118.6
O8—N4—O7	127.3 (8)	C12—C13—H13	118.6
N1—C1—C2	121.7 (6)	C13^ii—C14—C12	120.1 (5)
N1—C1—H1	119.1	C13^ii—C14—H14	119.9
C2—C1—H1	119.1	C12—C14—H14	119.9
C3—C2—C1	119.8 (6)	O6—C15—O5	126.7 (4)
C3—C2—H2	120.1	O6—C15—C16	118.8 (5)
C1—C2—H2	120.1	O5—C15—C16	114.5 (4)
C2—C3—C4	119.8 (6)	C17—C16—C18	117.9 (4)
C2—C3—H3	120.1	C17—C16—C15	120.0 (4)
C4—C3—H3	120.1	C18—C16—C15	122.0 (4)
C3—C4—C5	120.1 (6)	C16—C17—C18^iii	119.8 (4)
C3—C4—H4	119.9	C16—C17—H17	120.1
C5—C4—H4	119.9	C18^iii—C17—H17	120.1
N1—C5—C4	119.6 (5)	C17^iii—C18—C16	122.3 (4)
N1—C5—C6	115.2 (4)	C17^iii—C18—H18	118.9
C4—C5—C6	125.2 (5)	C16—C18—H18	118.9
N2—C6—C7	122.0 (5)
O5—Cu1—O1—C11	70.1 (3)	Cu1—N2—C6—C5	−1.9 (5)
N1—Cu1—O1—C11	−108.3 (3)	N1—C5—C6—N2	0.7 (6)
O5^i—Cu1—O1—C11	147.4 (3)	C4—C5—C6—N2	−177.1 (4)
O1—Cu1—O5—C15	−107.0 (3)	N1—C5—C6—C7	−178.0 (5)
N2—Cu1—O5—C15	67.7 (3)	C4—C5—C6—C7	4.2 (8)
O5^i—Cu1—O5—C15	163.7 (4)	N2—C6—C7—C8	−1.2 (9)
O1—Cu1—O5—Cu1^i	89.30 (14)	C5—C6—C7—C8	177.4 (6)
N2—Cu1—O5—Cu1^i	−96.01 (14)	C6—C7—C8—C9	2.8 (11)
O5^i—Cu1—O5—Cu1^i	0.0	C7—C8—C9—C10	−2.2 (10)
O1—Cu1—N1—C1	−7.7 (4)	C6—N2—C10—C9	1.6 (8)
N2—Cu1—N1—C1	177.4 (4)	Cu1—N2—C10—C9	−175.9 (4)
O5^i—Cu1—N1—C1	81.7 (4)	C8—C9—C10—N2	0.0 (9)
O1—Cu1—N1—C5	173.4 (3)	Cu1—O1—C11—O2	8.7 (7)
N2—Cu1—N1—C5	−1.5 (3)	Cu1—O1—C11—C12	−166.6 (3)
O5^i—Cu1—N1—C5	−97.1 (3)	O2—C11—C12—C13	149.7 (6)
O5—Cu1—N2—C10	1.0 (4)	O1—C11—C12—C13	−34.7 (7)
N1—Cu1—N2—C10	179.5 (4)	O2—C11—C12—C14	−33.1 (7)
O5^i—Cu1—N2—C10	−77.2 (4)	O1—C11—C12—C14	142.5 (5)
O5—Cu1—N2—C6	−176.6 (3)	C14—C12—C13—C14^ii	0.1 (9)
N1—Cu1—N2—C6	1.8 (3)	C11—C12—C13—C14^ii	177.3 (5)
O5^i—Cu1—N2—C6	105.2 (3)	C13—C12—C14—C13^ii	−0.1 (9)
C5—N1—C1—C2	−0.7 (7)	C11—C12—C14—C13^ii	−177.5 (5)
Cu1—N1—C1—C2	−179.5 (4)	Cu1—O5—C15—O6	−20.8 (7)
N1—C1—C2—C3	0.2 (8)	Cu1^i—O5—C15—O6	137.7 (4)
C1—C2—C3—C4	1.3 (9)	Cu1—O5—C15—C16	157.4 (3)
C2—C3—C4—C5	−2.1 (9)	Cu1^i—O5—C15—C16	−44.0 (5)
C1—N1—C5—C4	−0.2 (7)	O6—C15—C16—C17	127.5 (5)
Cu1—N1—C5—C4	178.8 (3)	O5—C15—C16—C17	−50.9 (6)
C1—N1—C5—C6	−178.1 (4)	O6—C15—C16—C18	−47.5 (7)
Cu1—N1—C5—C6	0.9 (5)	O5—C15—C16—C18	134.0 (5)
C3—C4—C5—N1	1.6 (8)	C18—C16—C17—C18^iii	−0.4 (7)
C3—C4—C5—C6	179.3 (5)	C15—C16—C17—C18^iii	−175.7 (4)
C10—N2—C6—C7	−1.0 (7)	C17—C16—C18—C17^iii	0.4 (8)
Cu1—N2—C6—C7	176.8 (4)	C15—C16—C18—C17^iii	175.6 (4)
C10—N2—C6—C5	−179.7 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O2	0.85 (6)	1.98 (6)	2.815 (6)	169 (6)
O1W—H1W2···O6^iv	0.85 (5)	2.09 (4)	2.879 (7)	155 (8)

Symmetry code: (iv) −x, −y, −z+1.