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

In the title compound, [Cu(C₈H₄O₄)(C₁₄H₈N₄)(H₂O)]·C₃H₇NO·H₂O, the Cu^II atom binds a water mol­ecule and is chelated by the pyrazinophenanthroline N-heterocycle. It is also linked covalently to a terephthalate dianion that lies on a special position of site symmetry. This dianion serves as a spacer to connect adjacent square-pyramidal metal atoms into a helical chain that propagates along the b axis of the monoclinic unit cell. The chain motif is consolidated into a layer structure by hydrogen bonds involving the coordinated and uncoordinated water mol­ecules. The Cu atom and the coordinated water mol­ecule lie on a mirror plane, while the N-heterocycle, the disordered uncoordinated water mol­ecule and disordered dimethyl­formamide solvent molecule lie about a mirror plane.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.050
• wR factor = 0.144
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level A
DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.
DIFF022_ALERT_1_A  _diffrn_standards_decay_% is missing
            Percentage decrease in standards intensity.
PLAT780_ALERT_1_A Coordinates do not Form a Properly Connected Set          ?

Alert level B
PLAT415_ALERT_2_B Short Inter D-H..H-X       H1W1   ..  H13C    ..       2.03 Ang.
PLAT415_ALERT_2_B Short Inter D-H..H-X       H1W1   ..  H13C    ..       2.03 Ang.
PLAT416_ALERT_2_B Short Intra D-H..H-D       H1W2   ..  H2W2    ..       1.86 Ang.
PLAT416_ALERT_2_B Short Intra D-H..H-D       H1W2   ..  H2W2    ..       1.86 Ang.

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.701     0.909
            Tmin(prime) and Tmax expected:      0.811     0.908
            RR(prime) =      0.863
            Please check that your absorption correction is appropriate.
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
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.86
PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ...    1197.00 Ang-3
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         N2
PLAT301_ALERT_3_C Main Residue  Disorder .........................       5.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4
PLAT731_ALERT_1_C Bond    Calc     0.84(4), Rep   0.850(10) ......       4.00 su-Ra
              O1W  -H1W2    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.84(4), Rep   0.850(10) ......       4.00 su-Ra
              O1W  -H2#     1.555   1.555

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

   3 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
  13 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
   6 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

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-terephthalato-κ²O:O'] N,N-dimethylformamide monohydrate]

Crystal data

[Cu(C8H4O4)(C14H8N4)(H2O)]·C3H7NO·H2O	F(000) = 586
Mr = 569.02	Dx = 1.578 Mg m^−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 9444 reflections
a = 7.275 (4) Å	θ = 3.2–27.5°
b = 13.970 (5) Å	µ = 0.97 mm^−1
c = 11.794 (5) Å	T = 293 K
β = 92.78 (2)°	Block, green
V = 1197 (1) Å^3	0.21 × 0.19 × 0.10 mm
Z = 2

Data collection

Rigaku R-AXIS RAPID IP diffractometer	2856 independent reflections
Radiation source: fine-focus sealed tube	2229 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→9
Tmin = 0.701, Tmax = 0.909	k = −16→18
11896 measured reflections	l = −15→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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.077P)^2 + 0.8938P] where P = (Fo^2 + 2Fc^2)/3
2856 reflections	(Δ/σ)max = 0.001
214 parameters	Δρmax = 0.85 e Å^−3
58 restraints	Δρmin = −0.56 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.35210 (8)	0.2500	0.64318 (4)	0.0386 (2)
O1	0.4201 (4)	0.3484 (2)	0.7528 (2)	0.0575 (7)
O2	0.1446 (4)	0.3936 (2)	0.8086 (2)	0.0617 (8)
O1W	0.6390 (5)	0.2500	0.5738 (3)	0.0607 (11)
H1W1	0.662 (7)	0.2500	0.5043 (13)	0.073*
H1W2	0.738 (4)	0.2500	0.614 (4)	0.073*
O2W	0.9645 (8)	0.260 (4)	0.6961 (5)	0.070 (7)	0.50
H2W1	1.036 (10)	0.302 (6)	0.726 (7)	0.084*	0.50
H2W2	0.889 (10)	0.242 (9)	0.745 (5)	0.084*	0.50
N1	0.2637 (4)	0.34436 (18)	0.5218 (2)	0.0375 (6)
N2	0.0266 (5)	0.3496 (3)	0.1299 (3)	0.0635 (10)
C1	0.3144 (5)	0.3923 (2)	0.8172 (3)	0.0433 (8)
C2	0.4119 (5)	0.4492 (2)	0.9116 (2)	0.0371 (7)
C3	0.6013 (5)	0.4521 (2)	0.9218 (3)	0.0429 (8)
H3	0.6701	0.4200	0.8693	0.051*
C4	0.6901 (5)	0.5024 (2)	1.0098 (3)	0.0419 (7)
H4	0.8180	0.5039	1.0161	0.050*
C5	0.1969 (4)	0.30106 (19)	0.4258 (2)	0.0328 (6)
C6	0.1358 (4)	0.3528 (2)	0.3294 (3)	0.0406 (7)
C7	0.1431 (6)	0.4526 (3)	0.3350 (3)	0.0565 (10)
H7	0.1010	0.4894	0.2734	0.068*
C8	0.2127 (7)	0.4954 (3)	0.4321 (3)	0.0641 (12)
H8	0.2206	0.5618	0.4365	0.077*
C9	0.2720 (6)	0.4390 (2)	0.5243 (3)	0.0523 (9)
H9	0.3189	0.4690	0.5899	0.063*
C10	0.0781 (5)	0.2997 (2)	0.2291 (2)	0.0434 (8)
C11	−0.0069 (5)	0.2992 (2)	0.0540 (3)	0.0437 (8)
H11	−0.0374	0.3286	−0.0151	0.052*
O5	0.6708 (10)	0.1582 (4)	0.3734 (5)	0.0651 (17)	0.50
N3	0.5780 (5)	0.2533 (16)	0.2253 (4)	0.0453 (12)	0.50
C12	0.6065 (15)	0.1672 (18)	0.2728 (10)	0.050 (4)	0.50
H12	0.5782	0.1126	0.2304	0.060*	0.50
C13	0.622 (2)	0.3392 (17)	0.2888 (12)	0.054 (4)	0.50
H13A	0.5098	0.3705	0.3079	0.080*	0.50
H13B	0.6925	0.3813	0.2438	0.080*	0.50
H13C	0.6917	0.3229	0.3572	0.080*	0.50
C14	0.5053 (9)	0.2628 (15)	0.1094 (5)	0.055 (3)	0.50
H14A	0.5976	0.2901	0.0637	0.082*	0.50
H14B	0.3992	0.3038	0.1075	0.082*	0.50
H14C	0.4709	0.2009	0.0802	0.082*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0572 (4)	0.0337 (3)	0.0237 (3)	0.000	−0.0115 (2)	0.000
O1	0.0702 (18)	0.0646 (17)	0.0363 (12)	0.0002 (14)	−0.0127 (12)	−0.0222 (12)
O2	0.0586 (19)	0.0634 (18)	0.0611 (16)	−0.0045 (13)	−0.0199 (13)	−0.0174 (14)
O1W	0.043 (2)	0.096 (3)	0.042 (2)	0.000	−0.0104 (16)	0.000
O2W	0.071 (3)	0.04 (2)	0.094 (4)	0.009 (7)	−0.046 (3)	0.000 (5)
N1	0.0464 (16)	0.0332 (13)	0.0321 (13)	0.0022 (11)	−0.0057 (11)	−0.0004 (10)
N2	0.059 (2)	0.070 (2)	0.062 (2)	0.0172 (17)	0.0069 (17)	0.0347 (19)
C1	0.063 (2)	0.0354 (16)	0.0301 (15)	−0.0047 (15)	−0.0139 (15)	0.0002 (12)
C2	0.0499 (19)	0.0323 (15)	0.0279 (14)	−0.0018 (13)	−0.0101 (13)	0.0006 (11)
C3	0.055 (2)	0.0411 (18)	0.0320 (15)	0.0001 (15)	−0.0023 (14)	−0.0053 (13)
C4	0.0433 (19)	0.0434 (18)	0.0384 (16)	−0.0021 (14)	−0.0059 (14)	−0.0036 (13)
C5	0.0315 (15)	0.0406 (16)	0.0258 (13)	0.0017 (12)	−0.0026 (11)	0.0037 (12)
C6	0.0361 (17)	0.0518 (19)	0.0338 (15)	0.0054 (14)	−0.0001 (13)	0.0084 (14)
C7	0.071 (3)	0.048 (2)	0.051 (2)	0.0125 (18)	−0.0009 (19)	0.0167 (17)
C8	0.100 (4)	0.0336 (18)	0.059 (2)	0.006 (2)	0.002 (2)	0.0102 (17)
C9	0.077 (3)	0.0325 (17)	0.0471 (19)	−0.0009 (17)	−0.0033 (18)	−0.0013 (14)
C10	0.0347 (17)	0.070 (2)	0.0246 (14)	0.0052 (15)	−0.0043 (12)	0.0070 (14)
C11	0.0313 (17)	0.0469 (19)	0.053 (2)	0.0046 (14)	0.0034 (15)	0.0080 (16)
O5	0.095 (5)	0.050 (3)	0.049 (3)	0.014 (3)	0.002 (3)	0.003 (2)
N3	0.048 (2)	0.043 (3)	0.045 (2)	0.003 (8)	0.0017 (18)	−0.003 (8)
C12	0.056 (7)	0.058 (8)	0.038 (5)	0.001 (5)	0.009 (5)	−0.003 (5)
C13	0.062 (7)	0.042 (6)	0.056 (7)	−0.003 (5)	0.004 (5)	0.001 (6)
C14	0.054 (3)	0.059 (10)	0.051 (3)	0.001 (5)	0.002 (3)	0.006 (4)

Geometric parameters (Å, º)

Cu1—O1	1.934 (2)	C5—C5^i	1.426 (5)
Cu1—O1^i	1.934 (2)	C6—C7	1.396 (5)
Cu1—N1	2.028 (3)	C6—C10	1.442 (4)
Cu1—N1^i	2.028 (3)	C7—C8	1.368 (5)
Cu1—O1W	2.279 (4)	C7—H7	0.9300
O1—C1	1.265 (4)	C8—C9	1.394 (5)
O2—C1	1.235 (5)	C8—H8	0.9300
O1W—H1W1	0.84 (1)	C9—H9	0.9300
O1W—H1W2	0.85 (1)	C10—C10^i	1.388 (6)
O2W—H2W1	0.85 (1)	C11—C11^i	1.374 (6)
O2W—H2W2	0.86 (1)	C11—H11	0.9300
N1—C9	1.324 (4)	O5—C12	1.261 (10)
N1—C5	1.353 (3)	N3—C12	1.338 (9)
N2—C11	1.156 (5)	N3—C13	1.442 (9)
N2—C10	1.397 (4)	N3—C14	1.448 (6)
C1—C2	1.516 (4)	C12—H12	0.9300
C2—C3	1.378 (5)	C13—H13A	0.9600
C2—C4^ii	1.391 (5)	C13—H13B	0.9600
C3—C4	1.387 (4)	C13—H13C	0.9600
C3—H3	0.9300	C14—H14A	0.9600
C4—C2^ii	1.391 (5)	C14—H14B	0.9600
C4—H4	0.9300	C14—H14C	0.9600
C5—C6	1.401 (4)
O1—Cu1—O1^i	90.5 (2)	C8—C7—C6	119.2 (3)
O1—Cu1—O1W	91.8 (2)	C8—C7—H7	120.4
O1—Cu1—N1	94.1 (1)	C6—C7—H7	120.4
O1—Cu1—N1^i	174.7 (1)	C7—C8—C9	119.6 (3)
O1W—Cu1—N1	90.6 (1)	C7—C8—H8	120.2
O1W—Cu1—N1^i	90.6 (1)	C9—C8—H8	120.2
N1—Cu1—N1^i	81.1 (1)	N1—C9—C8	122.3 (3)
C1—O1—Cu1	127.1 (3)	N1—C9—H9	118.8
Cu1—O1W—H1W1	125 (4)	C8—C9—H9	118.8
Cu1—O1W—H1W2	125 (3)	C10^i—C10—N2	119.9 (2)
H1W1—O1W—H1W2	110 (2)	C10^i—C10—C6	120.97 (17)
H2W1—O2W—H2W2	109 (2)	N2—C10—C6	119.1 (3)
C9—N1—C5	118.7 (3)	N2—C11—C11^i	127.5 (2)
C9—N1—Cu1	128.4 (2)	N2—C11—H11	116.2
C5—N1—Cu1	112.88 (19)	C11^i—C11—H11	116.2
C11—N2—C10	112.5 (4)	C12—N3—C13	120.3 (5)
O2—C1—O1	126.3 (3)	C12—N3—C14	121.3 (11)
O2—C1—C2	118.9 (3)	C13—N3—C14	118.4 (11)
O1—C1—C2	114.8 (3)	O5—C12—N3	121.8 (15)
C3—C2—C4^ii	119.4 (3)	O5—C12—H12	119.1
C3—C2—C1	120.6 (3)	N3—C12—H12	119.1
C4^ii—C2—C1	119.9 (3)	N3—C13—H13A	109.5
C2—C3—C4	120.5 (3)	N3—C13—H13B	109.5
C2—C3—H3	119.7	H13A—C13—H13B	109.5
C4—C3—H3	119.7	N3—C13—H13C	109.5
C3—C4—C2^ii	120.1 (3)	H13A—C13—H13C	109.5
C3—C4—H4	120.0	H13B—C13—H13C	109.5
C2^ii—C4—H4	120.0	N3—C14—H14A	109.5
N1—C5—C6	122.4 (3)	N3—C14—H14B	109.5
N1—C5—C5^i	116.57 (15)	H14A—C14—H14B	109.5
C6—C5—C5^i	121.04 (18)	N3—C14—H14C	109.5
C7—C6—C5	117.8 (3)	H14A—C14—H14C	109.5
C7—C6—C10	124.1 (3)	H14B—C14—H14C	109.5
C5—C6—C10	118.0 (3)
O1^i—Cu1—O1—C1	−95.8 (3)	Cu1—N1—C5—C5^i	0.8 (2)
N1—Cu1—O1—C1	81.6 (3)	N1—C5—C6—C7	−0.9 (5)
O1W—Cu1—O1—C1	172.4 (3)	C5^i—C5—C6—C7	−178.8 (3)
O1—Cu1—N1—C9	4.8 (3)	N1—C5—C6—C10	176.1 (3)
N1^i—Cu1—N1—C9	−177.6 (3)	C5^i—C5—C6—C10	−1.8 (4)
O1W—Cu1—N1—C9	−87.1 (3)	C5—C6—C7—C8	1.6 (6)
O1—Cu1—N1—C5	−178.6 (2)	C10—C6—C7—C8	−175.2 (4)
N1^i—Cu1—N1—C5	−0.9 (3)	C6—C7—C8—C9	−1.2 (7)
O1W—Cu1—N1—C5	89.6 (2)	C5—N1—C9—C8	0.6 (6)
Cu1—O1—C1—O2	−14.0 (5)	Cu1—N1—C9—C8	177.1 (3)
Cu1—O1—C1—C2	167.1 (2)	C7—C8—C9—N1	0.1 (7)
O2—C1—C2—C3	−177.9 (3)	C11—N2—C10—C10^i	−2.2 (4)
O1—C1—C2—C3	1.1 (4)	C11—N2—C10—C6	176.0 (3)
O2—C1—C2—C4^ii	3.4 (5)	C7—C6—C10—C10^i	178.6 (3)
O1—C1—C2—C4^ii	−177.6 (3)	C5—C6—C10—C10^i	1.8 (4)
C4^ii—C2—C3—C4	0.2 (5)	C7—C6—C10—N2	0.4 (5)
C1—C2—C3—C4	−178.5 (3)	C5—C6—C10—N2	−176.4 (3)
C2—C3—C4—C2^ii	−0.2 (5)	C10—N2—C11—C11^i	2.4 (4)
C9—N1—C5—C6	−0.2 (5)	C13—N3—C12—O5	0.3 (3)
Cu1—N1—C5—C6	−177.2 (2)	C14—N3—C12—O5	179.6 (3)
C9—N1—C5—C5^i	177.8 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O5	0.84 (1)	2.01 (1)	2.708 (7)	140 (1)
O1W—H1W2···O2W	0.85 (1)	1.87 (1)	2.716 (7)	175 (3)
O2W—H2W1···O2^iii	0.85 (1)	1.77 (5)	2.61 (4)	167 (9)

Symmetry code: (iii) x+1, y, z.