catena-Poly[[[aqua­(pyrazino[2,3-f][1,10]phenanthroline-κ2N,N′)copper(II)]-μ-isophthalato-κ2O:O′] N,N-dimethyl­formamide solvate monohydrate]

Che, G.-B.; Xu, Z.-L.; Ng, S.W.

doi:10.1107/S1600536806045107

catena-Poly[[[aqua(pyrazino[2,3-f][1,10]phenanthroline-κ²N,N′)copper(II)]-μ-isophthalato-κ²O:O′] N,N-dimethylformamide solvate monohydrate]

In the title compound, {[Cu(C₈H₄O₄)(C₁₄H₈N₄)(H₂O)]·C₃H₇NO·H₂O}_n, the Cu^II atom binds a water molecule and is chelated by the pyrazinophenanthroline N-heterocycle. It is also linked covalently to an isophthalate dianion that lies on a special position of site symmetry 2. The dianion serves as a spacer that connects adjacent square-pyramidal metal atoms into a zigzag chain propagating along the c axis of the orthorhombic unit cell. The chain motif is consolidated into a layer structure by hydrogen bonds involving both the coordinated and uncoordinated water molecules. The copper atom and the coordinated water molecule lie on a mirror plane, while the N-heterocycle, the disordered uncoordinated water molecule and the disordered dimethylformamide solvent molecule lie across a mirror plane.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806045107/sj2148sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806045107/sj2148Isup2.hkl Contains datablock I

CCDC reference: 630467

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R factor = 0.038
wR factor = 0.107
Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.552     0.845
            Tmin(prime) and Tmax expected:      0.819     0.840
            RR(prime) =      0.670
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.67
PLAT417_ALERT_2_B Short Inter D-H..H-D       H1W2   ..  H2W2    ..       1.95 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D       H1W2   ..  H2W2    ..       1.95 Ang.

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT301_ALERT_3_C Main Residue  Disorder .........................       6.00 Perc.
PLAT415_ALERT_2_C Short Inter D-H..H-X       H1W1   ..  H14C    ..       2.11 Ang.
PLAT415_ALERT_2_C Short Inter D-H..H-X       H1W1   ..  H14C    ..       2.11 Ang.
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........    O1<I>W<
                    CU1    O1<I>W<
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........    O1<I>W<
                    O1     CU1    O1<I>W<
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........    O1<I>W<
                    O1<I>W<CU1    N1
PLAT715_ALERT_1_C D-H     Unknown or Inconsistent Label ..........    O1<I>W<
PLAT715_ALERT_1_C D-H     Unknown or Inconsistent Label ..........    O1<I>W<
PLAT715_ALERT_1_C D-H     Unknown or Inconsistent Label ..........    O2<I>W<
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

  12 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2006).

catena-Poly[[[aqua(pyrazino[2,3-f][1,10]phenanthroline-κ²N,N')copper(II)]- µ-isophthalato-κ²O:O'] N,N-dimethylformamide solvate monohydrate] top

Crystal data top

[Cu(C₈H₄O₄)(C₁₄H₈N₄)(H₂O)]·C₃H₇NO·H₂O	F(000) = 1172
M_r = 569.02	D_x = 1.579 Mg m⁻³
Orthorhombic, Pbcm	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2c 2b	Cell parameters from 14093 reflections
a = 7.237 (2) Å	θ = 3.3–27.5°
b = 23.877 (6) Å	µ = 0.97 mm⁻¹
c = 13.848 (8) Å	T = 293 K
V = 2393 (2) Å³	Block, blue
Z = 4	0.20 × 0.19 × 0.18 mm

Data collection top

Rigaku RAXIS-RAPID IP diffractometer	2810 independent reflections
Radiation source: fine-focus sealed tube	2138 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
ω scans	θ_max = 27.5°, θ_min = 3.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→9
T_min = 0.552, T_max = 0.845	k = −30→30
20300 measured reflections	l = −17→17

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0575P)² + 0.5178P] where P = (F_o² + 2F_c²)/3
2810 reflections	(Δ/σ)_max = 0.001
215 parameters	Δρ_max = 0.32 e Å⁻³
57 restraints	Δρ_min = −0.46 e Å⁻³

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cu1	0.15835 (5)	0.076495 (14)	0.7500	0.03864 (15)
O1	0.0938 (3)	0.12947 (6)	0.84985 (15)	0.0547 (5)
O2	0.3681 (2)	0.16345 (7)	0.89469 (14)	0.0515 (5)
O1w	−0.1417 (3)	0.04030 (10)	0.7500	0.0598 (8)
H1w1	−0.170 (4)	0.0059 (5)	0.7500	0.072*
H1w2	−0.239 (3)	0.0599 (11)	0.7500	0.072*
O2w	0.5377 (5)	0.10369 (14)	0.758 (3)	0.061 (4)	0.50
H2w1	0.483 (7)	0.121 (2)	0.803 (4)	0.074*	0.50
H2w2	0.610 (7)	0.1262 (17)	0.729 (4)	0.074*	0.50
N1	0.2360 (3)	0.01659 (7)	0.65507 (13)	0.0358 (4)
N2	0.4488 (3)	−0.17407 (7)	0.64883 (16)	0.0481 (5)
C1	0.1976 (4)	0.16395 (8)	0.89414 (17)	0.0396 (5)
C2	0.0947 (3)	0.20856 (8)	0.94985 (16)	0.0343 (5)
C3	0.1893 (4)	0.2500	1.0000	0.0340 (6)
H3	0.3178	0.2500	1.0000	0.041*
C4	−0.0977 (3)	0.20896 (9)	0.94993 (18)	0.0428 (6)
H4	−0.1627	0.1816	0.9163	0.051*
C5	−0.1920 (5)	0.2500	1.0000	0.0467 (8)
H5	−0.3205	0.2500	1.0000	0.056*
C6	0.2971 (3)	−0.03074 (8)	0.69834 (14)	0.0315 (4)
C7	0.3516 (3)	−0.07805 (8)	0.64667 (16)	0.0355 (5)
C8	0.3434 (4)	−0.07574 (10)	0.54579 (19)	0.0518 (7)
H8	0.3810	−0.1061	0.5086	0.062*
C9	0.2792 (5)	−0.02815 (11)	0.5029 (2)	0.0622 (8)
H9	0.2706	−0.0261	0.4360	0.075*
C10	0.2269 (4)	0.01721 (10)	0.55919 (18)	0.0511 (6)
H10	0.1838	0.0493	0.5286	0.061*
C11	0.4055 (3)	−0.12784 (8)	0.69982 (17)	0.0363 (5)
C12	0.4878 (3)	−0.21934 (9)	0.70064 (18)	0.0514 (6)
H12	0.5162	−0.2524	0.6684	0.062*
O3	−0.1821 (6)	−0.06183 (15)	0.8352 (3)	0.0617 (11)	0.50
N3	−0.0919 (4)	−0.13586 (14)	0.7437 (12)	0.0413 (13)	0.50
C13	−0.1257 (10)	−0.1112 (4)	0.8290 (11)	0.045 (2)	0.50
H13	−0.1065	−0.1315	0.8854	0.054*	0.50
C14	−0.1198 (17)	−0.1065 (5)	0.6538 (12)	0.059 (4)	0.50
H14A	−0.2281	−0.1209	0.6223	0.089*	0.50
H14B	−0.0143	−0.1119	0.6128	0.089*	0.50
H14C	−0.1357	−0.0673	0.6664	0.089*	0.50
C15	−0.0273 (6)	−0.19346 (16)	0.7409 (18)	0.056 (2)	0.50
H15A	0.0856	−0.1966	0.7768	0.084*	0.50
H15B	−0.0058	−0.2043	0.6751	0.084*	0.50
H15C	−0.1191	−0.2175	0.7689	0.084*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0574 (3)	0.0203 (2)	0.0382 (3)	−0.00113 (15)	0.000	0.000
O1	0.0665 (11)	0.0318 (8)	0.0658 (14)	0.0000 (7)	−0.0039 (9)	−0.0186 (8)
O2	0.0560 (11)	0.0423 (10)	0.0561 (13)	0.0046 (7)	0.0052 (8)	−0.0119 (8)
O1w	0.0490 (14)	0.0374 (13)	0.093 (2)	0.0014 (10)	0.000	0.000
O2w	0.066 (2)	0.066 (2)	0.052 (12)	0.0236 (14)	−0.003 (5)	0.016 (8)
N1	0.0490 (11)	0.0277 (9)	0.0307 (11)	−0.0018 (7)	−0.0010 (8)	0.0029 (7)
N2	0.0607 (12)	0.0331 (10)	0.0504 (14)	0.0043 (8)	0.0087 (10)	−0.0056 (9)
C1	0.0644 (16)	0.0223 (10)	0.0320 (14)	0.0001 (9)	0.0013 (11)	0.0014 (8)
C2	0.0509 (12)	0.0239 (10)	0.0281 (12)	−0.0010 (8)	−0.0008 (10)	0.0016 (8)
C3	0.0434 (16)	0.0262 (14)	0.0324 (17)	0.000	0.000	0.0021 (12)
C4	0.0515 (13)	0.0328 (12)	0.0442 (15)	−0.0085 (9)	−0.0048 (11)	−0.0016 (10)
C5	0.0442 (18)	0.0465 (19)	0.050 (2)	0.000	0.000	−0.0021 (16)
C6	0.0379 (10)	0.0282 (10)	0.0286 (11)	−0.0044 (8)	0.0007 (9)	0.0001 (8)
C7	0.0456 (12)	0.0305 (11)	0.0306 (13)	−0.0012 (8)	0.0016 (9)	−0.0020 (8)
C8	0.083 (2)	0.0385 (13)	0.0337 (15)	0.0029 (12)	0.0070 (12)	−0.0059 (10)
C9	0.111 (2)	0.0489 (15)	0.0265 (14)	0.0036 (15)	0.0004 (15)	0.0008 (11)
C10	0.0817 (18)	0.0369 (13)	0.0346 (15)	0.0052 (11)	−0.0057 (13)	0.0060 (10)
C11	0.0381 (11)	0.0282 (10)	0.0426 (13)	0.0008 (8)	0.0041 (10)	−0.0023 (9)
C12	0.0581 (14)	0.0305 (11)	0.0655 (17)	0.0079 (10)	0.0066 (12)	−0.0052 (10)
O3	0.092 (3)	0.0386 (18)	0.055 (2)	0.0031 (18)	0.017 (2)	−0.0047 (17)
N3	0.0508 (16)	0.0376 (15)	0.036 (4)	−0.0020 (12)	0.007 (4)	−0.003 (5)
C13	0.056 (5)	0.040 (4)	0.040 (5)	−0.019 (3)	0.000 (3)	0.002 (3)
C14	0.071 (6)	0.058 (5)	0.050 (7)	0.004 (4)	0.001 (4)	0.010 (4)
C15	0.056 (2)	0.0413 (19)	0.071 (7)	0.0001 (16)	−0.007 (5)	0.005 (4)

Geometric parameters (Å, º) top

Cu1—O1	1.931 (2)	C6—C7	1.394 (3)
Cu1—O1ⁱ	1.931 (2)	C6—C6ⁱ	1.431 (4)
Cu1—N1ⁱ	2.022 (2)	C7—C8	1.399 (3)
Cu1—N1	2.022 (2)	C7—C11	1.452 (3)
Cu1—O1w	2.337 (2)	C8—C9	1.364 (3)
O1—C1	1.272 (3)	C8—H8	0.9300
O2—C1	1.234 (3)	C9—C10	1.387 (3)
O1w—H1w1	0.85 (1)	C9—H9	0.9300
O1w—H1w2	0.85 (1)	C10—H10	0.9300
O2w—H2w1	0.85 (1)	C11—C11ⁱ	1.390 (5)
O2w—H2w2	0.85 (1)	C12—C12ⁱ	1.367 (5)
N1—C10	1.329 (3)	C12—H12	0.9300
N1—C6	1.353 (2)	O3—C13	1.250 (8)
N2—C12	1.328 (3)	N3—C13	1.342 (8)
N2—C11	1.347 (3)	N3—C14	1.442 (8)
C1—C2	1.511 (3)	N3—C15	1.453 (5)
C2—C3	1.389 (3)	C13—H13	0.9300
C2—C4	1.392 (3)	C14—H14A	0.9600
C3—C2ⁱⁱ	1.389 (2)	C14—H14B	0.9600
C3—H3	0.9300	C14—H14C	0.9600
C4—C5	1.381 (3)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C5—C4ⁱⁱ	1.381 (3)	C15—H15C	0.9600
C5—H5	0.9300

O1—Cu1—O1ⁱ	91.4 (1)	C6—C7—C11	118.6 (2)
O1—Cu1—N1	174.8 (1)	C8—C7—C11	123.4 (2)
O1—Cu1—N1ⁱ	93.7 (1)	C9—C8—C7	118.8 (2)
O1—Cu1—O1w	91.0 (1)	C9—C8—H8	120.6
O1w—Cu1—N1	89.8 (1)	C7—C8—H8	120.6
O1w—Cu1—N1ⁱ	89.8 (1)	C8—C9—C10	119.9 (3)
N1—Cu1—N1ⁱ	81.1 (1)	C8—C9—H9	120.0
C1—O1—Cu1	128.79 (17)	C10—C9—H9	120.0
Cu1—O1w—H1w1	126 (2)	N1—C10—C9	122.6 (2)
Cu1—O1w—H1w2	125 (2)	N1—C10—H10	118.7
H1w1—O1w—H1w2	109 (2)	C9—C10—H10	118.7
H2w1—O2w—H2w2	109 (2)	N2—C11—C11ⁱ	121.61 (14)
C10—N1—C6	117.88 (19)	N2—C11—C7	117.9 (2)
C10—N1—Cu1	128.87 (16)	C11ⁱ—C11—C7	120.47 (12)
C6—N1—Cu1	113.18 (14)	N2—C12—C12ⁱ	122.71 (14)
C12—N2—C11	115.7 (2)	N2—C12—H12	118.6
O2—C1—O1	126.0 (2)	C12ⁱ—C12—H12	118.6
O2—C1—C2	119.7 (2)	C13—N3—C14	121.4 (4)
O1—C1—C2	114.3 (2)	C13—N3—C15	119.8 (11)
C3—C2—C4	119.2 (2)	C14—N3—C15	118.8 (11)
C3—C2—C1	121.0 (2)	O3—C13—N3	122.3 (9)
C4—C2—C1	119.9 (2)	O3—C13—H13	118.8
C2—C3—C2ⁱⁱ	121.0 (3)	N3—C13—H13	118.8
C2—C3—H3	119.5	N3—C14—H14A	109.5
C2ⁱⁱ—C3—H3	119.5	N3—C14—H14B	109.5
C5—C4—C2	120.0 (2)	H14A—C14—H14B	109.5
C5—C4—H4	120.0	N3—C14—H14C	109.5
C2—C4—H4	120.0	H14A—C14—H14C	109.5
C4ⁱⁱ—C5—C4	120.8 (3)	H14B—C14—H14C	109.5
C4ⁱⁱ—C5—H5	119.6	N3—C15—H15A	109.5
C4—C5—H5	119.6	N3—C15—H15B	109.5
N1—C6—C7	122.81 (19)	H15A—C15—H15B	109.5
N1—C6—C6ⁱ	116.28 (11)	N3—C15—H15C	109.5
C7—C6—C6ⁱ	120.88 (12)	H15A—C15—H15C	109.5
C6—C7—C8	117.9 (2)	H15B—C15—H15C	109.5

O1ⁱ—Cu1—O1—C1	−93.6 (2)	C10—N1—C6—C6ⁱ	−177.28 (17)
N1ⁱ—Cu1—O1—C1	85.5 (2)	Cu1—N1—C6—C6ⁱ	−0.07 (15)
O1w—Cu1—O1—C1	175.4 (2)	N1—C6—C7—C8	0.5 (3)
O1ⁱ—Cu1—N1—C10	−3.9 (2)	C6ⁱ—C6—C7—C8	178.24 (16)
N1ⁱ—Cu1—N1—C10	176.91 (19)	N1—C6—C7—C11	−176.67 (19)
O1w—Cu1—N1—C10	87.1 (2)	C6ⁱ—C6—C7—C11	1.1 (2)
O1ⁱ—Cu1—N1—C6	179.25 (15)	C6—C7—C8—C9	−1.4 (4)
N1ⁱ—Cu1—N1—C6	0.08 (17)	C11—C7—C8—C9	175.6 (2)
O1w—Cu1—N1—C6	−89.75 (14)	C7—C8—C9—C10	1.2 (4)
Cu1—O1—C1—O2	−14.3 (4)	C6—N1—C10—C9	−0.7 (4)
Cu1—O1—C1—C2	165.69 (15)	Cu1—N1—C10—C9	−177.5 (2)
O2—C1—C2—C3	1.6 (3)	C8—C9—C10—N1	−0.1 (5)
O1—C1—C2—C3	−178.45 (17)	C12—N2—C11—C11ⁱ	1.2 (3)
O2—C1—C2—C4	−179.5 (2)	C12—N2—C11—C7	−176.6 (2)
O1—C1—C2—C4	0.5 (3)	C6—C7—C11—N2	176.71 (19)
C4—C2—C3—C2ⁱⁱ	0.22 (15)	C8—C7—C11—N2	−0.3 (3)
C1—C2—C3—C2ⁱⁱ	179.1 (2)	C6—C7—C11—C11ⁱ	−1.1 (2)
C3—C2—C4—C5	−0.4 (3)	C8—C7—C11—C11ⁱ	−178.07 (17)
C1—C2—C4—C5	−179.37 (17)	C11—N2—C12—C12ⁱ	−1.2 (3)
C2—C4—C5—C4ⁱⁱ	0.22 (15)	C14—N3—C13—O3	−0.3 (3)
C10—N1—C6—C7	0.6 (3)	C15—N3—C13—O3	−179.7 (3)
Cu1—N1—C6—C7	177.78 (15)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w1···O3	0.85 (1)	2.00 (1)	2.725 (4)	142 (1)
O1w—H1w2···O2wⁱⁱⁱ	0.85 (1)	1.93 (1)	2.773 (5)	177 (2)
O2w—H2w1···O2	0.85 (1)	1.82 (4)	2.67 (3)	175 (6)

Symmetry code: (iii) x−1, y, z.

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catena-Poly[[[aqua­(pyrazino[2,3-f][1,10]phenanthroline-κ2N,N′)copper(II)]-μ-isophthalato-κ2O:O′] N,N-dimethyl­formamide solvate monohydrate]

Supporting information

Key indicators

checkCIF/PLATON results

catena-Poly[[[aqua(pyrazino[2,3-f][1,10]phenanthroline-κ²N,N′)copper(II)]-μ-isophthalato-κ²O:O′] N,N-dimethylformamide solvate monohydrate]