Aqua­chloro(4-cyano­benzoato-κO)(1,10-phenanthroline-κ²N,N′)copper(II) monohydrate

The reaction of copper(II) chloride with 4-cyano­benzoic acid and 1,10-phenanthroline in a mixture of di­methyl­form­amide and methanol gives the title complex, [CuCl(C₈H₄NO₂)(C₁₂H₈N₂)(H₂O)]·H₂O. The Cu^II ion is coordinated by one 1,10-phenanthroline, one water mol­ecule, one Cl atom, and one 4-cyano­benzoate ligand. In the crystal structure, there are O—H...Cl hydrogen bonds and π–π-stacking interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.034
• wR factor = 0.088
• Data-to-parameter ratio = 11.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



ABSTM_02  Alert B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
          Tmin and Tmax reported:      0.382     0.655
          Tmin' and Tmax expected:      0.568     0.655
          RR' =      0.672
          Please check that your absorption correction is appropriate.


 Alert Level C:



PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C17    -   C20      =       1.44 Ang.


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 1 Alert Level C = Please check

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Computing details

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

(I)

Crystal data

[CuCl(C8H4NO2)(C12H8N2)(H2O)]·H2O	Z = 2
Mr = 461.35	F(000) = 470
Triclinic, P1	Dx = 1.603 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.5460 (6) Å	Cell parameters from 3099 reflections
b = 9.4402 (8) Å	θ = 5.2–55.6°
c = 15.6840 (14) Å	µ = 1.32 mm^−1
α = 87.438 (2)°	T = 293 K
β = 88.035 (2)°	Plate, blue
γ = 81.046 (2)°	0.42 × 0.35 × 0.32 mm
V = 956.07 (15) Å^3

Data collection

Bruker CCD area-detector diffractometer	3871 independent reflections
Radiation source: fine-focus sealed tube	3377 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
φ and ω scans	θmax = 26.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→7
Tmin = 0.382, Tmax = 0.655	k = −9→11
5452 measured reflections	l = −19→19

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.088	w = 1/[σ^2(Fo^2) + (0.0477P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.009
3871 reflections	Δρmax = 0.45 e Å^−3
327 parameters	Δρmin = −0.42 e Å^−3
4 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0119 (16)

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
Cu	0.78123 (4)	0.74728 (3)	0.210863 (17)	0.03227 (12)
Cl	0.61785 (10)	0.70256 (7)	0.07312 (4)	0.04587 (17)
O1	0.6570 (2)	0.61367 (17)	0.28995 (11)	0.0405 (4)
O2	0.9229 (3)	0.4378 (2)	0.31183 (12)	0.0539 (5)
O3	1.0454 (3)	0.6177 (2)	0.20226 (14)	0.0472 (5)
O4	0.2239 (3)	0.5500 (2)	0.05264 (14)	0.0566 (5)
N1	0.9123 (3)	0.91331 (19)	0.15965 (11)	0.0321 (4)
N2	0.5592 (3)	0.90732 (19)	0.24506 (11)	0.0308 (4)
N3	0.1193 (6)	0.1367 (4)	0.5859 (2)	0.1113 (14)
C1	1.0918 (4)	0.9128 (3)	0.11687 (15)	0.0398 (5)
C2	1.1513 (4)	1.0370 (3)	0.07990 (16)	0.0440 (6)
C3	1.0254 (4)	1.1656 (3)	0.08750 (16)	0.0450 (6)
C4	0.8364 (4)	1.1716 (3)	0.13311 (14)	0.0377 (5)
C5	0.6931 (5)	1.2997 (3)	0.14641 (16)	0.0445 (6)
C6	0.5147 (5)	1.2968 (3)	0.19150 (16)	0.0438 (6)
C7	0.4602 (4)	1.1653 (2)	0.22806 (14)	0.0343 (5)
C8	0.2792 (4)	1.1538 (3)	0.27636 (15)	0.0401 (6)
C9	0.2425 (4)	1.0226 (3)	0.30711 (16)	0.0419 (6)
C10	0.3846 (4)	0.9007 (3)	0.28963 (15)	0.0383 (5)
C11	0.5972 (3)	1.0382 (2)	0.21531 (13)	0.0303 (5)
C12	0.7880 (3)	1.0408 (2)	0.16787 (13)	0.0311 (5)
C13	0.7394 (4)	0.4950 (2)	0.32306 (14)	0.0351 (5)
C14	0.6034 (4)	0.4164 (2)	0.38111 (14)	0.0346 (5)
C15	0.6862 (4)	0.2881 (3)	0.42268 (16)	0.0441 (6)
C16	0.5642 (5)	0.2156 (3)	0.47681 (17)	0.0524 (7)
C17	0.3569 (4)	0.2698 (3)	0.48847 (15)	0.0465 (6)
C18	0.2721 (4)	0.3962 (3)	0.44667 (16)	0.0456 (6)
C19	0.3958 (4)	0.4695 (3)	0.39329 (15)	0.0397 (5)
C20	0.2247 (5)	0.1951 (4)	0.5436 (2)	0.0666 (9)
H1	1.175 (4)	0.828 (2)	0.1113 (14)	0.026 (6)*
H2	1.278 (5)	1.021 (3)	0.0517 (17)	0.057 (8)*
H3	1.067 (4)	1.246 (3)	0.0637 (15)	0.043 (7)*
H4	0.734 (4)	1.378 (2)	0.1275 (16)	0.047 (7)*
H5	0.424 (4)	1.379 (3)	0.2000 (16)	0.044 (7)*
H6	0.191 (4)	1.235 (3)	0.2890 (15)	0.045 (7)*
H7	0.123 (4)	1.009 (3)	0.3403 (16)	0.048 (7)*
H8	0.353 (4)	0.813 (3)	0.3082 (15)	0.038 (7)*
H9	0.825 (3)	0.260 (3)	0.4174 (16)	0.046 (7)*
H10	0.620 (5)	0.135 (3)	0.5070 (19)	0.070 (9)*
H11	0.133 (4)	0.433 (3)	0.4534 (16)	0.043 (7)*
H12	0.337 (4)	0.551 (3)	0.3622 (16)	0.047 (7)*
H13	1.080 (5)	0.594 (3)	0.152 (2)	0.071 (11)*
H14	1.030 (6)	0.550 (4)	0.236 (2)	0.085 (12)*
H15	0.337 (3)	0.582 (3)	0.0570 (19)	0.060 (9)*
H16	0.254 (5)	0.479 (2)	0.0234 (17)	0.058 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu	0.02873 (17)	0.02632 (17)	0.03958 (18)	0.00012 (11)	0.00631 (11)	0.00193 (11)
Cl	0.0445 (3)	0.0481 (4)	0.0471 (3)	−0.0121 (3)	0.0032 (3)	−0.0115 (3)
O1	0.0371 (9)	0.0296 (8)	0.0502 (9)	0.0029 (7)	0.0093 (7)	0.0105 (7)
O2	0.0355 (10)	0.0519 (11)	0.0660 (12)	0.0106 (8)	0.0065 (8)	0.0229 (9)
O3	0.0384 (10)	0.0432 (11)	0.0534 (12)	0.0083 (8)	0.0131 (9)	0.0094 (9)
O4	0.0524 (13)	0.0554 (13)	0.0612 (12)	−0.0078 (10)	0.0182 (10)	−0.0119 (10)
N1	0.0291 (10)	0.0320 (10)	0.0350 (10)	−0.0048 (8)	0.0011 (8)	−0.0011 (8)
N2	0.0294 (9)	0.0273 (9)	0.0342 (9)	−0.0013 (7)	0.0027 (7)	0.0008 (7)
N3	0.102 (3)	0.144 (3)	0.099 (2)	−0.071 (3)	0.000 (2)	0.050 (2)
C1	0.0325 (13)	0.0461 (15)	0.0410 (13)	−0.0068 (11)	0.0022 (10)	−0.0051 (11)
C2	0.0386 (14)	0.0582 (17)	0.0382 (13)	−0.0192 (12)	0.0067 (11)	−0.0004 (12)
C3	0.0541 (16)	0.0463 (15)	0.0390 (13)	−0.0239 (13)	−0.0027 (11)	0.0052 (12)
C4	0.0470 (14)	0.0372 (13)	0.0312 (11)	−0.0140 (11)	−0.0054 (10)	0.0030 (10)
C5	0.0640 (17)	0.0284 (13)	0.0417 (13)	−0.0105 (12)	−0.0067 (12)	0.0070 (10)
C6	0.0598 (17)	0.0276 (13)	0.0414 (13)	0.0027 (12)	−0.0083 (12)	−0.0002 (10)
C7	0.0400 (13)	0.0306 (12)	0.0311 (11)	0.0003 (9)	−0.0064 (9)	−0.0032 (9)
C8	0.0396 (13)	0.0360 (13)	0.0407 (13)	0.0084 (11)	−0.0022 (10)	−0.0070 (11)
C9	0.0335 (13)	0.0471 (15)	0.0427 (13)	0.0000 (11)	0.0071 (11)	−0.0047 (11)
C10	0.0374 (13)	0.0337 (13)	0.0426 (13)	−0.0039 (10)	0.0046 (10)	0.0018 (10)
C11	0.0318 (11)	0.0288 (11)	0.0300 (10)	−0.0032 (9)	−0.0049 (9)	−0.0001 (9)
C12	0.0338 (12)	0.0315 (12)	0.0288 (10)	−0.0076 (9)	−0.0038 (9)	−0.0001 (9)
C13	0.0374 (13)	0.0328 (12)	0.0336 (11)	−0.0018 (10)	0.0010 (10)	0.0015 (9)
C14	0.0401 (13)	0.0309 (12)	0.0324 (11)	−0.0043 (10)	−0.0016 (10)	−0.0001 (9)
C15	0.0435 (15)	0.0388 (14)	0.0477 (14)	−0.0014 (11)	−0.0008 (12)	0.0058 (11)
C16	0.069 (2)	0.0397 (15)	0.0482 (15)	−0.0111 (14)	−0.0073 (14)	0.0139 (12)
C17	0.0571 (17)	0.0500 (15)	0.0363 (13)	−0.0227 (13)	0.0007 (12)	0.0030 (11)
C18	0.0421 (15)	0.0504 (16)	0.0449 (14)	−0.0098 (12)	0.0042 (12)	−0.0026 (12)
C19	0.0431 (14)	0.0360 (13)	0.0386 (13)	−0.0036 (11)	0.0015 (10)	0.0016 (10)
C20	0.075 (2)	0.073 (2)	0.0570 (18)	−0.0319 (18)	−0.0044 (16)	0.0127 (16)

Geometric parameters (Å, º)

Cu—O3	1.9609 (17)	C5—C6	1.348 (4)
Cu—O1	1.9751 (15)	C5—H4	0.866 (16)
Cu—N2	2.0046 (18)	C6—C7	1.434 (3)
Cu—N1	2.0242 (18)	C6—H5	0.91 (3)
Cu—Cl	2.5238 (7)	C7—C11	1.399 (3)
O1—C13	1.263 (3)	C7—C8	1.401 (3)
O2—C13	1.248 (3)	C8—C9	1.362 (4)
O3—H13	0.84 (3)	C8—H6	0.91 (2)
O3—H14	0.82 (4)	C9—C10	1.394 (3)
O4—H15	0.849 (18)	C9—H7	0.95 (3)
O4—H16	0.823 (18)	C10—H8	0.92 (2)
N1—C1	1.332 (3)	C11—C12	1.435 (3)
N1—C12	1.353 (3)	C13—C14	1.504 (3)
N2—C10	1.327 (3)	C14—C19	1.383 (3)
N2—C11	1.357 (3)	C14—C15	1.392 (3)
N3—C20	1.129 (4)	C15—C16	1.378 (4)
C1—C2	1.389 (4)	C15—H9	0.905 (17)
C1—H1	0.90 (2)	C16—C17	1.383 (4)
C2—C3	1.364 (4)	C16—H10	0.91 (3)
C2—H2	0.92 (3)	C17—C18	1.383 (4)
C3—C4	1.403 (4)	C17—C20	1.442 (4)
C3—H3	0.91 (2)	C18—C19	1.383 (3)
C4—C12	1.404 (3)	C18—H11	0.93 (3)
C4—C5	1.429 (4)	C19—H12	0.93 (3)
O3—Cu—O1	92.94 (7)	C11—C7—C6	118.2 (2)
O3—Cu—N2	162.57 (8)	C8—C7—C6	124.9 (2)
O1—Cu—N2	89.82 (7)	C9—C8—C7	119.7 (2)
O3—Cu—N1	91.20 (8)	C9—C8—H6	121.0 (16)
O1—Cu—N1	164.20 (7)	C7—C8—H6	119.2 (16)
N2—Cu—N1	81.84 (7)	C8—C9—C10	119.8 (2)
O3—Cu—Cl	101.12 (7)	C8—C9—H7	122.9 (16)
O1—Cu—Cl	100.41 (6)	C10—C9—H7	117.3 (16)
N2—Cu—Cl	95.28 (5)	N2—C10—C9	122.3 (2)
N1—Cu—Cl	93.73 (5)	N2—C10—H8	119.5 (15)
C13—O1—Cu	129.04 (15)	C9—C10—H8	118.2 (15)
Cu—O3—H13	114 (2)	N2—C11—C7	123.3 (2)
Cu—O3—H14	104 (3)	N2—C11—C12	116.27 (19)
H13—O3—H14	115 (3)	C7—C11—C12	120.4 (2)
H15—O4—H16	104 (3)	N1—C12—C4	123.8 (2)
C1—N1—C12	117.8 (2)	N1—C12—C11	116.48 (19)
C1—N1—Cu	129.82 (17)	C4—C12—C11	119.8 (2)
C12—N1—Cu	112.30 (14)	O2—C13—O1	125.8 (2)
C10—N2—C11	118.00 (19)	O2—C13—C14	117.5 (2)
C10—N2—Cu	129.05 (16)	O1—C13—C14	116.7 (2)
C11—N2—Cu	112.92 (14)	C19—C14—C15	119.4 (2)
N1—C1—C2	122.3 (2)	C19—C14—C13	120.8 (2)
N1—C1—H1	117.8 (14)	C15—C14—C13	119.8 (2)
C2—C1—H1	119.9 (14)	C16—C15—C14	120.5 (3)
C3—C2—C1	120.1 (2)	C16—C15—H9	121.6 (16)
C3—C2—H2	126.9 (18)	C14—C15—H9	117.6 (16)
C1—C2—H2	113.1 (18)	C15—C16—C17	119.5 (2)
C2—C3—C4	119.7 (2)	C15—C16—H10	121 (2)
C2—C3—H3	119.0 (17)	C17—C16—H10	120 (2)
C4—C3—H3	121.3 (17)	C16—C17—C18	120.5 (2)
C3—C4—C12	116.5 (2)	C16—C17—C20	120.8 (3)
C3—C4—C5	124.8 (2)	C18—C17—C20	118.7 (3)
C12—C4—C5	118.7 (2)	C17—C18—C19	119.7 (3)
C6—C5—C4	121.3 (2)	C17—C18—H11	121.2 (16)
C6—C5—H4	123.2 (19)	C19—C18—H11	119.1 (16)
C4—C5—H4	115.3 (19)	C18—C19—C14	120.3 (2)
C5—C6—C7	121.6 (2)	C18—C19—H12	119.6 (16)
C5—C6—H5	121.0 (17)	C14—C19—H12	119.9 (16)
C7—C6—H5	117.4 (17)	N3—C20—C17	179.1 (4)
C11—C7—C8	116.9 (2)
O3—Cu—O1—C13	4.2 (2)	C10—N2—C11—C7	−1.1 (3)
N2—Cu—O1—C13	−158.6 (2)	Cu—N2—C11—C7	177.35 (17)
N1—Cu—O1—C13	−100.8 (3)	C10—N2—C11—C12	179.67 (19)
Cl—Cu—O1—C13	106.1 (2)	Cu—N2—C11—C12	−1.9 (2)
O3—Cu—N1—C1	15.9 (2)	C8—C7—C11—N2	1.9 (3)
O1—Cu—N1—C1	121.1 (3)	C6—C7—C11—N2	−178.3 (2)
N2—Cu—N1—C1	179.8 (2)	C8—C7—C11—C12	−178.9 (2)
Cl—Cu—N1—C1	−85.3 (2)	C6—C7—C11—C12	0.9 (3)
O3—Cu—N1—C12	−168.02 (16)	C1—N1—C12—C4	0.8 (3)
O1—Cu—N1—C12	−62.8 (3)	Cu—N1—C12—C4	−175.83 (17)
N2—Cu—N1—C12	−4.05 (14)	C1—N1—C12—C11	−179.13 (19)
Cl—Cu—N1—C12	90.76 (14)	Cu—N1—C12—C11	4.3 (2)
O3—Cu—N2—C10	−111.3 (3)	C3—C4—C12—N1	0.2 (3)
O1—Cu—N2—C10	−12.0 (2)	C5—C4—C12—N1	−179.7 (2)
N1—Cu—N2—C10	−178.5 (2)	C3—C4—C12—C11	−179.9 (2)
Cl—Cu—N2—C10	88.4 (2)	C5—C4—C12—C11	0.3 (3)
O3—Cu—N2—C11	70.5 (3)	N2—C11—C12—N1	−1.7 (3)
O1—Cu—N2—C11	169.74 (15)	C7—C11—C12—N1	179.12 (19)
N1—Cu—N2—C11	3.19 (15)	N2—C11—C12—C4	178.42 (19)
Cl—Cu—N2—C11	−89.82 (14)	C7—C11—C12—C4	−0.8 (3)
C12—N1—C1—C2	−1.2 (3)	Cu—O1—C13—O2	0.3 (4)
Cu—N1—C1—C2	174.70 (18)	Cu—O1—C13—C14	−179.67 (15)
N1—C1—C2—C3	0.7 (4)	O2—C13—C14—C19	−176.7 (2)
C1—C2—C3—C4	0.3 (4)	O1—C13—C14—C19	3.3 (3)
C2—C3—C4—C12	−0.7 (4)	O2—C13—C14—C15	2.7 (3)
C2—C3—C4—C5	179.1 (2)	O1—C13—C14—C15	−177.2 (2)
C3—C4—C5—C6	−179.6 (2)	C19—C14—C15—C16	−1.2 (4)
C12—C4—C5—C6	0.2 (4)	C13—C14—C15—C16	179.3 (2)
C4—C5—C6—C7	−0.1 (4)	C14—C15—C16—C17	1.2 (4)
C5—C6—C7—C11	−0.5 (4)	C15—C16—C17—C18	−0.4 (4)
C5—C6—C7—C8	179.3 (2)	C15—C16—C17—C20	179.0 (3)
C11—C7—C8—C9	−1.0 (3)	C16—C17—C18—C19	−0.5 (4)
C6—C7—C8—C9	179.2 (2)	C20—C17—C18—C19	−179.8 (3)
C7—C8—C9—C10	−0.6 (4)	C17—C18—C19—C14	0.5 (4)
C11—N2—C10—C9	−0.6 (4)	C15—C14—C19—C18	0.4 (4)
Cu—N2—C10—C9	−178.82 (18)	C13—C14—C19—C18	179.9 (2)
C8—C9—C10—N2	1.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H13···O4^i	0.84 (3)	1.82 (4)	2.645 (3)	164 (3)
O3—H14···O2	0.82 (4)	1.76 (4)	2.559 (3)	163 (4)
O4—H15···Cl	0.85 (2)	2.33 (2)	3.175 (2)	171 (3)
O4—H16···Cl^ii	0.82 (2)	2.37 (2)	3.187 (2)	170 (3)

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