Aqua­(4-formyl­benzoato-κO)(nitrato-κO)(1,10-phenanthroline-κ2N,N′)copper(II)

Deng, Z.-P.; Gao, S.; Huo, L.-H.; Zhao, H.

doi:10.1107/S1600536807049744

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Aqua(4-formylbenzoato-κO)(nitrato-κO)(1,10-phenanthroline-κ²N,N′)copper(II)

Z.-P. Deng, S. Gao, L.-H. Huo and H. Zhao

In the title complex, [Cu(C₈H₅O₃)(NO₃)(C₁₂H₈N₂)(H₂O)], the Cu^II atom adopts a distorted square-pyramidal coordination geometry with an O atom of the nitrate group occupying the apex of the pyramid. The complex molecules are linked into ribbons along the a axis via hydrogen bonding between the water molecule and the nitro anion. π–π stacking interactions between the 4-formylbenzoate and phenanthroline ligands assemble two ribbons into a larger one-dimensional structure. The centroid-to-centroid distances between the overlapping six-membered rings are 3.634 (3) and 3.722 (3) Å.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049744/gk2110sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049744/gk2110Isup2.hkl Contains datablock I

CCDC reference: 667167

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Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.006 Å
R factor = 0.049
wR factor = 0.157
Data-to-parameter ratio = 14.8

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No syntax errors found



Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)       3000 Deg.
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1         (2)       2.13
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3

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

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

Comment top

In our previous work, we have reported the synthesis and structure of complex [Cu(C₈H₅O₃)₂(H₂O)₂].2H₂O, (I) (Deng et al., 2006), which can be obtained by the reaction of Cu(X)₂ (X = Ac, NO₃, Cl) and 4-formylbenzoic acid in a aqueous solution. We have noticed that in the presence of 4-formylbenzoic acid the anion X was not coordinating to the copper(II) atom. But for the title complex, we introduced the 1,10-phenanthroline ligand to the system of Cu(NO₃)₂ and 4-formylbenzoic acid in a H₂O/EtOH solution, and obtained a new complex [Cu(NO₃)(C₈H₅O₃)(C₁₂H₈N₂)(H₂O)], (II), in which the copper(II) atom is five-coordinated by nitrate group and formylbenzoate carboxylate group in monodentate mode, 1.10-phenanthroline ligand in chelating mode as well as a water molecule (Fig.1). Adjacent complex molecules are linked into a one-dimensional chain structure via hydrogen-bonding interactions and π-π stacking interactions between the benzene rings of phenanthroline and 4-formylbenzoato ligand, with centroid-centroid distances of 3.634 (3) (Cg1 and Cg2) and 3.722 (3) Å (Cg2 and Cg3) [Cg1: C15ⁱ—C18ⁱ/N2ⁱ/C19ⁱ; Cg2: C2ⁱⁱ—C7ⁱⁱ; Cg3: C12—C15/C19—C20, symmetry code: (I) x - 1,y,z; (II) -x + 1,-y + 1,-z + 1; Fig.2].

Related literature top

For literature on copper 4-formylbenzoate complexes, see: Deng et al. (2006).

Experimental top

Copper(II) nitrate hexahydrate (1.48 g, 5 mmol) was added to a H₂O/EtOH solution (1:1 v/v) of 4-formylbenzoic acid (1.5 g, 10 mmol) and 1,10-phenanthroline (0.99 g 5 mmol). Sodium hydroxide (0.1 M) was added dropwise until pH = 5 was reached. Blue single crystals separated from the filtered solution after several days. CH&N analysis. Calc. for C₂₀H₁₅N₃O₇Cu: C 50.80, H 3.20, N 8.89. Found: C 50.85, H 3.24, N 8.82.

Structure description top

For literature on copper 4-formylbenzoate complexes, see: Deng et al. (2006).

Computing details top

Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO (Rigaku Corporation, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); 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 (Sheldrick, 1997).

Figures top

	Fig. 1. Molecular structure of the title compound with 30% probability ellipsoid for the non-H atoms. Dashed lines indicate O—H···O hydrogen bonds.
	Fig. 2. one-dimensional-chain structure of the title complex along the a axis formed by hydrogen-bonding and π-π stacking interactions, with the O—H···O hydrogen bonds denoted by dashed lines. H atoms not involved in hydrogen bonding have been omitted. Cg1, Cg2 and Cg3 represent the centroids of adjacent benzene rings of phen ligands and 4-formylbenzoato ligand, as defined in the Comment.

Aqua(4-formylbenzoato-κO)(nitrato-κO)(1,10-phenanthroline- κ²N,N')copper(II) top

Crystal data top

[Cu(C₈H₅O₃)(NO₃)(C₁₂H₈N₂)(H₂O)]	Z = 2
M_r = 472.89	F(000) = 482
Triclinic, P1	D_x = 1.670 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6070 (15) Å	Cell parameters from 4431 reflections
b = 9.0859 (18) Å	θ = 3.5–27.4°
c = 14.147 (3) Å	µ = 1.21 mm⁻¹
α = 88.88 (3)°	T = 295 K
β = 74.49 (3)°	Prism, blue
γ = 86.60 (3)°	0.32 × 0.25 × 0.18 mm
V = 940.5 (4) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	4247 independent reflections
Radiation source: fine-focus sealed tube	2405 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
Detector resolution: 10.000 pixels mm^-1	θ_max = 27.4°, θ_min = 3.5°
ω scans	h = −9→7
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −11→11
T_min = 0.699, T_max = 0.807	l = −18→18
9201 measured reflections

Refinement top

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0732P)²] where P = (F_o² + 2F_c²)/3
4247 reflections	(Δ/σ)_max < 0.001
286 parameters	Δρ_max = 0.67 e Å⁻³
3 restraints	Δρ_min = −0.68 e Å⁻³

Crystal data top

[Cu(C₈H₅O₃)(NO₃)(C₁₂H₈N₂)(H₂O)]	γ = 86.60 (3)°
M_r = 472.89	V = 940.5 (4) Å³
Triclinic, P1	Z = 2
a = 7.6070 (15) Å	Mo Kα radiation
b = 9.0859 (18) Å	µ = 1.21 mm⁻¹
c = 14.147 (3) Å	T = 295 K
α = 88.88 (3)°	0.32 × 0.25 × 0.18 mm
β = 74.49 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4247 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2405 reflections with I > 2σ(I)
T_min = 0.699, T_max = 0.807	R_int = 0.048
9201 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	3 restraints
wR(F²) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.67 e Å⁻³
4247 reflections	Δρ_min = −0.68 e Å⁻³
286 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	0.54659 (7)	0.45156 (5)	0.68949 (4)	0.0463 (2)
O1W	0.3833 (4)	0.2877 (3)	0.7229 (2)	0.0532 (7)
H1W1	0.411 (5)	0.242 (5)	0.6689 (19)	0.080*
H1W2	0.2684 (17)	0.300 (5)	0.745 (3)	0.080*
O1	0.6488 (4)	0.3948 (3)	0.5529 (2)	0.0536 (7)
O2	0.5177 (5)	0.1807 (4)	0.5543 (3)	0.0758 (10)
O3	1.1474 (6)	0.2219 (5)	0.0636 (3)	0.0959 (13)
O4	0.7526 (4)	0.3261 (4)	0.7633 (2)	0.0685 (10)
O5	0.9981 (5)	0.2915 (5)	0.6474 (3)	0.0885 (12)
O6	1.0143 (4)	0.3075 (4)	0.7949 (2)	0.0653 (9)
N1	0.4366 (4)	0.5431 (4)	0.8214 (2)	0.0470 (8)
N2	0.6552 (4)	0.6481 (4)	0.6598 (2)	0.0429 (8)
N3	0.9214 (5)	0.3087 (4)	0.7339 (3)	0.0462 (8)
C1	0.6249 (6)	0.2757 (4)	0.5128 (3)	0.0484 (10)
C2	0.7352 (5)	0.2457 (4)	0.4095 (3)	0.0461 (10)
C3	0.8376 (6)	0.3544 (5)	0.3519 (3)	0.0489 (10)
H3	0.8364	0.4483	0.3771	0.059*
C4	0.9389 (6)	0.3223 (5)	0.2587 (3)	0.0527 (11)
H4	1.0070	0.3947	0.2209	0.063*
C5	0.9418 (6)	0.1814 (5)	0.2190 (3)	0.0514 (10)
C6	0.8392 (6)	0.0743 (5)	0.2771 (3)	0.0537 (11)
H6	0.8400	−0.0197	0.2520	0.064*
C7	0.7369 (6)	0.1062 (4)	0.3709 (3)	0.0512 (10)
H7	0.6685	0.0341	0.4088	0.061*
C8	1.0505 (7)	0.1427 (6)	0.1195 (4)	0.0686 (14)
H8	1.0431	0.0476	0.0982	0.082*
C9	0.3303 (6)	0.4855 (5)	0.9034 (3)	0.0581 (12)
H9	0.3038	0.3869	0.9036	0.070*
C10	0.2590 (7)	0.5672 (6)	0.9875 (3)	0.0668 (13)
H10	0.1885	0.5226	1.0434	0.080*
C11	0.2912 (7)	0.7120 (6)	0.9890 (3)	0.0641 (13)
H11	0.2408	0.7670	1.0455	0.077*
C12	0.4011 (6)	0.7796 (5)	0.9049 (3)	0.0507 (11)
C13	0.4415 (6)	0.9304 (5)	0.8971 (4)	0.0589 (12)
H13	0.3901	0.9930	0.9496	0.071*
C14	0.5541 (6)	0.9851 (5)	0.8140 (4)	0.0574 (12)
H14	0.5790	1.0844	0.8110	0.069*
C15	0.6352 (6)	0.8924 (5)	0.7309 (3)	0.0487 (10)
C16	0.7539 (6)	0.9401 (5)	0.6428 (3)	0.0553 (11)
H16	0.7877	1.0373	0.6359	0.066*
C17	0.8188 (6)	0.8433 (5)	0.5681 (3)	0.0576 (11)
H17	0.8985	0.8737	0.5100	0.069*
C18	0.7654 (6)	0.6971 (5)	0.5787 (3)	0.0529 (11)
H18	0.8096	0.6327	0.5263	0.063*
C19	0.5920 (5)	0.7451 (4)	0.7358 (3)	0.0440 (9)
C20	0.4725 (5)	0.6878 (4)	0.8236 (3)	0.0449 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0447 (3)	0.0530 (3)	0.0389 (3)	−0.0098 (2)	−0.0057 (2)	−0.0038 (2)
O1W	0.0412 (16)	0.0584 (18)	0.055 (2)	−0.0149 (13)	−0.0018 (14)	−0.0017 (14)
O1	0.0620 (19)	0.0583 (17)	0.0393 (17)	−0.0189 (14)	−0.0075 (14)	−0.0080 (13)
O2	0.078 (2)	0.065 (2)	0.070 (2)	−0.0312 (17)	0.0103 (19)	−0.0187 (17)
O3	0.101 (3)	0.104 (3)	0.065 (3)	0.008 (2)	0.005 (2)	0.003 (2)
O4	0.0388 (18)	0.103 (3)	0.059 (2)	0.0005 (16)	−0.0078 (16)	0.0154 (18)
O5	0.075 (3)	0.137 (3)	0.043 (2)	−0.007 (2)	0.0047 (19)	−0.018 (2)
O6	0.0442 (18)	0.099 (2)	0.051 (2)	−0.0018 (16)	−0.0079 (16)	−0.0120 (17)
N1	0.0404 (19)	0.055 (2)	0.043 (2)	−0.0061 (15)	−0.0053 (16)	−0.0023 (16)
N2	0.0417 (19)	0.0525 (19)	0.0313 (18)	−0.0106 (14)	−0.0024 (15)	−0.0031 (14)
N3	0.042 (2)	0.0527 (19)	0.040 (2)	−0.0091 (15)	−0.0017 (17)	−0.0012 (15)
C1	0.052 (3)	0.048 (2)	0.046 (3)	−0.0050 (18)	−0.014 (2)	−0.0095 (19)
C2	0.042 (2)	0.056 (2)	0.042 (2)	−0.0051 (18)	−0.0116 (19)	−0.0055 (19)
C3	0.055 (3)	0.050 (2)	0.042 (3)	−0.0082 (19)	−0.012 (2)	−0.0044 (18)
C4	0.058 (3)	0.050 (2)	0.049 (3)	−0.0087 (19)	−0.012 (2)	−0.001 (2)
C5	0.050 (3)	0.057 (2)	0.047 (3)	−0.0014 (19)	−0.014 (2)	−0.006 (2)
C6	0.056 (3)	0.055 (2)	0.050 (3)	−0.004 (2)	−0.012 (2)	−0.015 (2)
C7	0.051 (3)	0.049 (2)	0.055 (3)	−0.0085 (18)	−0.014 (2)	−0.009 (2)
C8	0.063 (3)	0.084 (4)	0.053 (3)	0.001 (3)	−0.007 (3)	0.001 (3)
C9	0.057 (3)	0.071 (3)	0.042 (3)	−0.010 (2)	−0.003 (2)	0.004 (2)
C10	0.066 (3)	0.083 (4)	0.039 (3)	−0.010 (3)	0.008 (2)	0.001 (2)
C11	0.059 (3)	0.085 (4)	0.041 (3)	0.003 (2)	−0.001 (2)	−0.019 (2)
C12	0.050 (3)	0.066 (3)	0.036 (2)	0.005 (2)	−0.011 (2)	−0.013 (2)
C13	0.066 (3)	0.061 (3)	0.053 (3)	0.006 (2)	−0.021 (2)	−0.020 (2)
C14	0.063 (3)	0.054 (2)	0.062 (3)	0.000 (2)	−0.028 (3)	−0.012 (2)
C15	0.048 (3)	0.055 (2)	0.047 (3)	−0.0047 (19)	−0.020 (2)	−0.005 (2)
C16	0.063 (3)	0.054 (2)	0.052 (3)	−0.019 (2)	−0.018 (2)	0.003 (2)
C17	0.064 (3)	0.066 (3)	0.043 (3)	−0.020 (2)	−0.011 (2)	−0.002 (2)
C18	0.051 (3)	0.070 (3)	0.036 (2)	−0.018 (2)	−0.004 (2)	−0.004 (2)
C19	0.042 (2)	0.056 (2)	0.035 (2)	−0.0035 (17)	−0.0119 (18)	−0.0058 (18)
C20	0.041 (2)	0.052 (2)	0.042 (2)	0.0027 (18)	−0.0132 (19)	−0.0045 (19)

Geometric parameters (Å, º) top

Cu1—O1	1.947 (3)	C5—C8	1.467 (6)
Cu1—O1W	1.965 (3)	C6—C7	1.374 (6)
Cu1—N2	2.002 (3)	C6—H6	0.9300
Cu1—N1	2.004 (3)	C7—H7	0.9300
Cu1—O4	2.337 (3)	C8—H8	0.9300
O1W—H1W1	0.85 (3)	C9—C10	1.379 (7)
O1W—H1W2	0.85 (3)	C9—H9	0.9300
O1—C1	1.276 (5)	C10—C11	1.354 (7)
O2—C1	1.250 (5)	C10—H10	0.9300
O3—C8	1.190 (6)	C11—C12	1.411 (6)
O4—N3	1.241 (4)	C11—H11	0.9300
O5—N3	1.215 (4)	C12—C20	1.401 (6)
O6—N3	1.252 (4)	C12—C13	1.418 (6)
N1—C9	1.341 (5)	C13—C14	1.360 (7)
N1—C20	1.362 (5)	C13—H13	0.9300
N2—C18	1.314 (5)	C14—C15	1.436 (6)
N2—C19	1.370 (5)	C14—H14	0.9300
C1—C2	1.499 (6)	C15—C19	1.392 (6)
C2—C7	1.388 (6)	C15—C16	1.407 (6)
C2—C3	1.403 (6)	C16—C17	1.357 (6)
C3—C4	1.365 (6)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.406 (6)
C4—C5	1.405 (6)	C17—H17	0.9300
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.396 (6)	C19—C20	1.438 (6)

O1—Cu1—O1W	95.24 (13)	C6—C7—C2	120.3 (4)
O1—Cu1—N2	89.81 (13)	C6—C7—H7	119.9
O1W—Cu1—N2	165.89 (13)	C2—C7—H7	119.9
O1—Cu1—N1	170.66 (12)	O3—C8—C5	125.9 (5)
O1W—Cu1—N1	91.10 (13)	O3—C8—H8	117.1
N2—Cu1—N1	82.47 (13)	C5—C8—H8	117.1
O1—Cu1—O4	101.06 (13)	N1—C9—C10	122.4 (5)
O1W—Cu1—O4	90.02 (12)	N1—C9—H9	118.8
N2—Cu1—O4	101.96 (13)	C10—C9—H9	118.8
N1—Cu1—O4	85.75 (13)	C11—C10—C9	120.4 (5)
Cu1—O1W—H1W1	101 (3)	C11—C10—H10	119.8
Cu1—O1W—H1W2	123 (3)	C9—C10—H10	119.8
H1W1—O1W—H1W2	111 (4)	C10—C11—C12	120.1 (4)
C1—O1—Cu1	126.9 (3)	C10—C11—H11	120.0
N3—O4—Cu1	129.6 (3)	C12—C11—H11	120.0
C9—N1—C20	117.3 (4)	C20—C12—C11	115.9 (4)
C9—N1—Cu1	130.1 (3)	C20—C12—C13	118.9 (4)
C20—N1—Cu1	112.6 (3)	C11—C12—C13	125.2 (4)
C18—N2—C19	117.6 (4)	C14—C13—C12	121.2 (4)
C18—N2—Cu1	129.9 (3)	C14—C13—H13	119.4
C19—N2—Cu1	112.3 (3)	C12—C13—H13	119.4
O5—N3—O4	121.4 (4)	C13—C14—C15	121.1 (4)
O5—N3—O6	119.4 (4)	C13—C14—H14	119.4
O4—N3—O6	119.2 (4)	C15—C14—H14	119.4
O2—C1—O1	124.5 (4)	C19—C15—C16	116.8 (4)
O2—C1—C2	117.5 (4)	C19—C15—C14	118.6 (4)
O1—C1—C2	118.0 (4)	C16—C15—C14	124.6 (4)
C7—C2—C3	119.6 (4)	C17—C16—C15	119.5 (4)
C7—C2—C1	118.8 (4)	C17—C16—H16	120.3
C3—C2—C1	121.6 (4)	C15—C16—H16	120.3
C4—C3—C2	119.9 (4)	C16—C17—C18	120.0 (4)
C4—C3—H3	120.0	C16—C17—H17	120.0
C2—C3—H3	120.0	C18—C17—H17	120.0
C3—C4—C5	120.9 (4)	N2—C18—C17	122.4 (4)
C3—C4—H4	119.5	N2—C18—H18	118.8
C5—C4—H4	119.5	C17—C18—H18	118.8
C6—C5—C4	118.5 (4)	N2—C19—C15	123.7 (4)
C6—C5—C8	119.1 (4)	N2—C19—C20	116.2 (4)
C4—C5—C8	122.4 (4)	C15—C19—C20	120.1 (4)
C7—C6—C5	120.7 (4)	N1—C20—C12	123.9 (4)
C7—C6—H6	119.6	N1—C20—C19	116.0 (4)
C5—C6—H6	119.6	C12—C20—C19	120.1 (4)

O1W—Cu1—O1—C1	−8.8 (4)	C6—C5—C8—O3	−177.9 (5)
N2—Cu1—O1—C1	−175.6 (4)	C4—C5—C8—O3	1.3 (8)
O4—Cu1—O1—C1	82.3 (4)	C20—N1—C9—C10	−0.1 (6)
O1—Cu1—O4—N3	40.4 (4)	Cu1—N1—C9—C10	−177.0 (3)
O1W—Cu1—O4—N3	135.8 (4)	N1—C9—C10—C11	1.6 (8)
N2—Cu1—O4—N3	−51.8 (4)	C9—C10—C11—C12	−1.2 (8)
N1—Cu1—O4—N3	−133.1 (4)	C10—C11—C12—C20	−0.6 (7)
O1W—Cu1—N1—C9	15.0 (4)	C10—C11—C12—C13	178.8 (4)
N2—Cu1—N1—C9	−177.6 (4)	C20—C12—C13—C14	−2.9 (6)
O4—Cu1—N1—C9	−74.9 (4)	C11—C12—C13—C14	177.7 (4)
O1W—Cu1—N1—C20	−162.0 (3)	C12—C13—C14—C15	0.4 (7)
N2—Cu1—N1—C20	5.4 (3)	C13—C14—C15—C19	1.8 (6)
O4—Cu1—N1—C20	108.1 (3)	C13—C14—C15—C16	−179.5 (4)
O1—Cu1—N2—C18	−6.0 (4)	C19—C15—C16—C17	0.4 (6)
O1W—Cu1—N2—C18	−117.2 (6)	C14—C15—C16—C17	−178.3 (4)
N1—Cu1—N2—C18	179.3 (4)	C15—C16—C17—C18	0.8 (7)
O4—Cu1—N2—C18	95.3 (4)	C19—N2—C18—C17	0.0 (6)
O1—Cu1—N2—C19	169.6 (3)	Cu1—N2—C18—C17	175.3 (3)
O1W—Cu1—N2—C19	58.4 (6)	C16—C17—C18—N2	−1.0 (7)
N1—Cu1—N2—C19	−5.2 (3)	C18—N2—C19—C15	1.3 (6)
O4—Cu1—N2—C19	−89.2 (3)	Cu1—N2—C19—C15	−174.8 (3)
Cu1—O4—N3—O5	−36.2 (6)	C18—N2—C19—C20	−179.7 (4)
Cu1—O4—N3—O6	144.4 (3)	Cu1—N2—C19—C20	4.1 (4)
Cu1—O1—C1—O2	6.3 (7)	C16—C15—C19—N2	−1.5 (6)
Cu1—O1—C1—C2	−172.4 (2)	C14—C15—C19—N2	177.3 (4)
O2—C1—C2—C7	−10.6 (6)	C16—C15—C19—C20	179.6 (4)
O1—C1—C2—C7	168.3 (4)	C14—C15—C19—C20	−1.6 (6)
O2—C1—C2—C3	170.1 (4)	C9—N1—C20—C12	−1.9 (6)
O1—C1—C2—C3	−11.1 (6)	Cu1—N1—C20—C12	175.5 (3)
C7—C2—C3—C4	−0.5 (6)	C9—N1—C20—C19	177.8 (4)
C1—C2—C3—C4	178.9 (4)	Cu1—N1—C20—C19	−4.8 (4)
C2—C3—C4—C5	0.3 (6)	C11—C12—C20—N1	2.2 (6)
C3—C4—C5—C6	−0.2 (7)	C13—C12—C20—N1	−177.2 (4)
C3—C4—C5—C8	−179.4 (4)	C11—C12—C20—C19	−177.5 (4)
C4—C5—C6—C7	0.3 (6)	C13—C12—C20—C19	3.1 (6)
C8—C5—C6—C7	179.5 (4)	N2—C19—C20—N1	0.4 (5)
C5—C6—C7—C2	−0.4 (6)	C15—C19—C20—N1	179.4 (3)
C3—C2—C7—C6	0.5 (6)	N2—C19—C20—C12	−179.8 (3)
C1—C2—C7—C6	−178.9 (4)	C15—C19—C20—C12	−0.9 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O2	0.85 (3)	1.70 (2)	2.520 (5)	164 (5)
O1W—H1W2···O6ⁱ	0.85 (3)	1.87 (1)	2.714 (4)	175 (5)

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[Cu(C₈H₅O₃)(NO₃)(C₁₂H₈N₂)(H₂O)]
M_r	472.89
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	7.6070 (15), 9.0859 (18), 14.147 (3)
α, β, γ (°)	88.88 (3), 74.49 (3), 86.60 (3)
V (Å³)	940.5 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.21
Crystal size (mm)	0.32 × 0.25 × 0.18

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.699, 0.807
No. of measured, independent and observed [I > 2σ(I)] reflections	9201, 4247, 2405
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.157, 1.09
No. of reflections	4247
No. of parameters	286
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.68

Computer programs: RAPID-AUTO (Rigaku Corporation, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976).

Selected bond lengths (Å) top

Cu1—O1	1.947 (3)	Cu1—N1	2.004 (3)
Cu1—O1W	1.965 (3)	Cu1—O4	2.337 (3)
Cu1—N2	2.002 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O2	0.85 (3)	1.696 (15)	2.520 (5)	164 (5)
O1W—H1W2···O6ⁱ	0.85 (3)	1.870 (12)	2.714 (4)	175 (5)

Symmetry code: (i) x−1, y, z.

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