Methanol[4-nitro-2-(pyridin-2-ylmethyl­imino­methyl)phenolato](thio­cyanato)copper(II)

The title compound, [Cu(C₁₃H₁₀N₃O₃)(NCS)(CH₄O)], is a mononuclear copper(II) complex. The Cu^II atom has a square-pyramidal geometry. In the basal plane, the Cu atom is coordinated by two N atoms and one O atom of the Schiff base, and by the N atom of a thio­cyanate anion. The apical position is occupied by the O atom of a coordinated MeOH mol­ecule. In the crystal structure, the mol­ecules are linked via inter­molecular O—H...O hydrogen bonds, forming chains parallel to the b axis.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.043
• wR factor = 0.120
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.48
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     -   C14     ..       5.02 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT432_ALERT_2_C Short Inter X...Y Contact  C7     ..  C14     ..       3.17 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Methanol[4-nitro-2-(pyridin-2- ylmethyliminomethyl)phenolato](thiocyanato)copper(II)

Crystal data

[Cu(C13H10N3O3)(NCS)(CH4O)]	F(000) = 836
Mr = 409.90	Dx = 1.616 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3174 reflections
a = 10.539 (2) Å	θ = 2.3–24.4°
b = 15.986 (2) Å	µ = 1.45 mm^−1
c = 10.905 (2) Å	T = 298 K
β = 113.480 (2)°	Block, blue
V = 1685.1 (5) Å^3	0.25 × 0.20 × 0.12 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	3837 independent reflections
Radiation source: fine-focus sealed tube	2734 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.714, Tmax = 0.845	k = −20→20
14081 measured reflections	l = −13→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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0605P)^2 + 0.2163P] where = P = (Fo^2 + 2Fc^2)/3
3837 reflections	(Δ/σ)max < 0.001
230 parameters	Δρmax = 0.78 e Å^−3
1 restraint	Δρmin = −0.22 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wRand 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
Cu1	0.17005 (4)	0.94424 (2)	1.06402 (3)	0.04288 (14)
S1	0.23425 (11)	0.96158 (7)	1.51463 (9)	0.0706 (3)
O1	0.0768 (4)	1.22576 (18)	0.4953 (3)	0.0931 (9)
O2	0.1358 (3)	1.33212 (17)	0.6253 (3)	0.0904 (9)
O3	0.1919 (3)	1.06323 (12)	1.0488 (2)	0.0560 (6)
O4	0.3993 (3)	0.91438 (18)	1.1146 (3)	0.0695 (7)
N1	0.1168 (3)	1.2567 (2)	0.6062 (3)	0.0664 (8)
N2	0.0929 (3)	0.93021 (14)	0.8711 (2)	0.0433 (6)
N3	0.1267 (3)	0.82129 (15)	1.0579 (2)	0.0463 (6)
N4	0.2103 (3)	0.95644 (16)	1.2528 (3)	0.0533 (7)
C1	0.1328 (3)	1.07003 (18)	0.8127 (3)	0.0421 (7)
C2	0.1807 (3)	1.10501 (18)	0.9433 (3)	0.0462 (7)
C3	0.2143 (4)	1.1905 (2)	0.9560 (3)	0.0605 (9)
H3	0.2504	1.2143	1.0408	0.073*
C4	0.1959 (4)	1.2400 (2)	0.8479 (4)	0.0610 (9)
H4	0.2171	1.2967	0.8588	0.073*
C5	0.1449 (3)	1.2039 (2)	0.7219 (3)	0.0509 (8)
C6	0.1153 (3)	1.1210 (2)	0.7038 (3)	0.0482 (7)
H6	0.0833	1.0983	0.6183	0.058*
C7	0.0901 (3)	0.98462 (19)	0.7844 (3)	0.0443 (7)
H7	0.0578	0.9674	0.6956	0.053*
C8	0.0315 (4)	0.84861 (19)	0.8212 (3)	0.0576 (8)
H8A	0.0669	0.8275	0.7575	0.069*
H8B	−0.0681	0.8541	0.7758	0.069*
C9	0.0662 (3)	0.78847 (19)	0.9359 (3)	0.0489 (7)
C10	0.0350 (4)	0.7049 (2)	0.9144 (4)	0.0627 (9)
H10	−0.0077	0.6839	0.8280	0.075*
C11	0.0683 (4)	0.6526 (2)	1.0239 (4)	0.0675 (10)
H11	0.0477	0.5959	1.0121	0.081*
C12	0.1322 (4)	0.6854 (2)	1.1500 (4)	0.0680 (10)
H12	0.1570	0.6512	1.2249	0.082*
C13	0.1588 (4)	0.7698 (2)	1.1634 (3)	0.0577 (8)
H13	0.2007	0.7922	1.2489	0.069*
C14	0.2222 (3)	0.95849 (17)	1.3634 (3)	0.0439 (7)
C15	0.5049 (4)	0.9722 (3)	1.1738 (5)	0.0859 (13)
H15A	0.4984	1.0157	1.1108	0.129*
H15B	0.5928	0.9447	1.2004	0.129*
H15C	0.4963	0.9961	1.2509	0.129*
H4A	0.399 (4)	0.886 (2)	1.045 (2)	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0525 (2)	0.0399 (2)	0.0322 (2)	−0.00068 (15)	0.01267 (16)	−0.00033 (14)
S1	0.0848 (7)	0.0877 (7)	0.0358 (5)	−0.0009 (5)	0.0202 (5)	−0.0072 (4)
O1	0.140 (3)	0.082 (2)	0.0483 (16)	−0.0121 (18)	0.0283 (17)	0.0138 (14)
O2	0.139 (3)	0.0577 (17)	0.0761 (19)	−0.0019 (17)	0.0449 (18)	0.0212 (14)
O3	0.0910 (18)	0.0388 (12)	0.0354 (12)	−0.0009 (11)	0.0222 (12)	−0.0028 (9)
O4	0.0576 (15)	0.0849 (17)	0.0636 (17)	−0.0068 (13)	0.0216 (13)	−0.0343 (13)
N1	0.074 (2)	0.066 (2)	0.063 (2)	0.0031 (16)	0.0302 (17)	0.0203 (16)
N2	0.0466 (14)	0.0421 (13)	0.0345 (13)	−0.0012 (10)	0.0092 (11)	−0.0020 (10)
N3	0.0461 (14)	0.0421 (13)	0.0439 (14)	−0.0029 (11)	0.0107 (11)	0.0032 (11)
N4	0.0655 (18)	0.0551 (17)	0.0394 (15)	−0.0003 (13)	0.0209 (13)	0.0001 (12)
C1	0.0434 (16)	0.0448 (16)	0.0381 (16)	0.0031 (12)	0.0163 (13)	0.0004 (12)
C2	0.0548 (18)	0.0418 (16)	0.0411 (17)	0.0042 (13)	0.0183 (14)	0.0034 (13)
C3	0.087 (3)	0.0486 (19)	0.0425 (18)	−0.0066 (17)	0.0217 (17)	−0.0067 (14)
C4	0.079 (2)	0.0449 (18)	0.063 (2)	−0.0030 (16)	0.0314 (19)	0.0050 (16)
C5	0.0560 (19)	0.0541 (19)	0.0449 (18)	0.0015 (15)	0.0227 (15)	0.0109 (14)
C6	0.0503 (18)	0.0556 (19)	0.0366 (16)	0.0017 (14)	0.0151 (14)	0.0026 (13)
C7	0.0476 (17)	0.0489 (17)	0.0319 (15)	0.0043 (13)	0.0110 (13)	−0.0028 (12)
C8	0.066 (2)	0.0488 (18)	0.0435 (17)	−0.0092 (16)	0.0063 (15)	−0.0064 (14)
C9	0.0463 (17)	0.0448 (16)	0.0486 (18)	−0.0015 (13)	0.0114 (14)	−0.0023 (14)
C10	0.064 (2)	0.0478 (19)	0.063 (2)	−0.0053 (16)	0.0114 (18)	−0.0108 (16)
C11	0.072 (2)	0.0409 (18)	0.082 (3)	−0.0027 (16)	0.022 (2)	−0.0001 (18)
C12	0.080 (3)	0.0465 (19)	0.069 (2)	−0.0009 (17)	0.020 (2)	0.0109 (17)
C13	0.061 (2)	0.0517 (19)	0.0515 (19)	−0.0029 (15)	0.0130 (16)	0.0069 (15)
C14	0.0475 (17)	0.0372 (15)	0.0435 (17)	0.0009 (12)	0.0145 (14)	−0.0012 (12)
C15	0.069 (3)	0.103 (3)	0.080 (3)	−0.024 (2)	0.024 (2)	−0.020 (3)

Geometric parameters (Å, º)

Cu1—O3	1.931 (2)	C3—C4	1.367 (4)
Cu1—N4	1.939 (3)	C3—H3	0.9300
Cu1—N2	1.943 (2)	C4—C5	1.386 (5)
Cu1—N3	2.013 (2)	C4—H4	0.9300
Cu1—O4	2.304 (3)	C5—C6	1.357 (4)
S1—C14	1.603 (3)	C6—H6	0.9300
O1—N1	1.216 (4)	C7—H7	0.9300
O2—N1	1.227 (4)	C8—C9	1.503 (4)
O3—C2	1.294 (3)	C8—H8A	0.9700
O4—C15	1.392 (5)	C8—H8B	0.9700
O4—H4A	0.88 (3)	C9—C10	1.374 (4)
N1—C5	1.447 (4)	C10—C11	1.383 (5)
N2—C7	1.277 (4)	C10—H10	0.9300
N2—C8	1.461 (4)	C11—C12	1.372 (5)
N3—C9	1.332 (4)	C11—H11	0.9300
N3—C13	1.344 (4)	C12—C13	1.374 (5)
N4—C14	1.163 (4)	C12—H12	0.9300
C1—C6	1.391 (4)	C13—H13	0.9300
C1—C2	1.422 (4)	C15—H15A	0.9600
C1—C7	1.432 (4)	C15—H15B	0.9600
C2—C3	1.405 (4)	C15—H15C	0.9600
O3—Cu1—N4	90.51 (10)	C6—C5—N1	119.2 (3)
O3—Cu1—N2	91.92 (9)	C4—C5—N1	119.0 (3)
N4—Cu1—N2	168.94 (11)	C5—C6—C1	120.2 (3)
O3—Cu1—N3	172.83 (10)	C5—C6—H6	119.9
N4—Cu1—N3	94.85 (11)	C1—C6—H6	119.9
N2—Cu1—N3	81.93 (10)	N2—C7—C1	125.2 (3)
O3—Cu1—O4	94.29 (11)	N2—C7—H7	117.4
N4—Cu1—O4	90.08 (11)	C1—C7—H7	117.4
N2—Cu1—O4	100.49 (10)	N2—C8—C9	109.6 (2)
N3—Cu1—O4	90.46 (10)	N2—C8—H8A	109.7
C2—O3—Cu1	127.81 (19)	C9—C8—H8A	109.7
C15—O4—Cu1	122.8 (3)	N2—C8—H8B	109.7
C15—O4—H4A	118 (2)	C9—C8—H8B	109.7
Cu1—O4—H4A	105 (2)	H8A—C8—H8B	108.2
O1—N1—O2	122.5 (3)	N3—C9—C10	122.7 (3)
O1—N1—C5	120.0 (3)	N3—C9—C8	116.1 (3)
O2—N1—C5	117.6 (3)	C10—C9—C8	121.1 (3)
C7—N2—C8	117.2 (3)	C9—C10—C11	118.6 (3)
C7—N2—Cu1	126.8 (2)	C9—C10—H10	120.7
C8—N2—Cu1	116.00 (19)	C11—C10—H10	120.7
C9—N3—C13	118.1 (3)	C12—C11—C10	119.3 (3)
C9—N3—Cu1	115.5 (2)	C12—C11—H11	120.3
C13—N3—Cu1	126.4 (2)	C10—C11—H11	120.3
C14—N4—Cu1	172.7 (3)	C11—C12—C13	118.7 (3)
C6—C1—C2	119.9 (3)	C11—C12—H12	120.7
C6—C1—C7	116.8 (3)	C13—C12—H12	120.7
C2—C1—C7	123.1 (3)	N3—C13—C12	122.6 (3)
O3—C2—C3	119.0 (3)	N3—C13—H13	118.7
O3—C2—C1	123.9 (3)	C12—C13—H13	118.7
C3—C2—C1	117.1 (3)	N4—C14—S1	178.5 (3)
C4—C3—C2	122.3 (3)	O4—C15—H15A	109.5
C4—C3—H3	118.8	O4—C15—H15B	109.5
C2—C3—H3	118.8	H15A—C15—H15B	109.5
C3—C4—C5	118.6 (3)	O4—C15—H15C	109.5
C3—C4—H4	120.7	H15A—C15—H15C	109.5
C5—C4—H4	120.7	H15B—C15—H15C	109.5
C6—C5—C4	121.8 (3)
N4—Cu1—O3—C2	179.4 (3)	C3—C4—C5—C6	−1.1 (5)
N2—Cu1—O3—C2	−11.4 (3)	C3—C4—C5—N1	176.2 (3)
O4—Cu1—O3—C2	89.3 (3)	O1—N1—C5—C6	−5.3 (5)
O3—Cu1—O4—C15	25.6 (3)	O2—N1—C5—C6	175.2 (3)
N4—Cu1—O4—C15	−64.9 (3)	O1—N1—C5—C4	177.3 (3)
N2—Cu1—O4—C15	118.3 (3)	O2—N1—C5—C4	−2.2 (5)
N3—Cu1—O4—C15	−159.8 (3)	C4—C5—C6—C1	1.5 (5)
O3—Cu1—N2—C7	10.4 (3)	N1—C5—C6—C1	−175.8 (3)
N4—Cu1—N2—C7	113.0 (5)	C2—C1—C6—C5	0.5 (5)
N3—Cu1—N2—C7	−173.3 (3)	C7—C1—C6—C5	175.7 (3)
O4—Cu1—N2—C7	−84.3 (3)	C8—N2—C7—C1	173.7 (3)
O3—Cu1—N2—C8	−169.4 (2)	Cu1—N2—C7—C1	−6.1 (4)
N4—Cu1—N2—C8	−66.8 (6)	C6—C1—C7—N2	−176.7 (3)
N3—Cu1—N2—C8	6.9 (2)	C2—C1—C7—N2	−1.8 (5)
O4—Cu1—N2—C8	95.9 (2)	C7—N2—C8—C9	170.0 (3)
N4—Cu1—N3—C9	167.5 (2)	Cu1—N2—C8—C9	−10.2 (3)
N2—Cu1—N3—C9	−1.8 (2)	C13—N3—C9—C10	0.4 (5)
O4—Cu1—N3—C9	−102.3 (2)	Cu1—N3—C9—C10	177.3 (3)
N2—Cu1—N3—C13	174.8 (3)	C13—N3—C9—C8	179.6 (3)
O4—Cu1—N3—C13	74.2 (3)	Cu1—N3—C9—C8	−3.5 (4)
Cu1—O3—C2—C3	−173.6 (2)	N2—C8—C9—N3	8.7 (4)
Cu1—O3—C2—C1	7.9 (5)	N2—C8—C9—C10	−172.1 (3)
C6—C1—C2—O3	175.7 (3)	N3—C9—C10—C11	−0.3 (5)
C7—C1—C2—O3	0.9 (5)	C8—C9—C10—C11	−179.5 (3)
C6—C1—C2—C3	−2.8 (4)	C9—C10—C11—C12	−0.5 (5)
C7—C1—C2—C3	−177.6 (3)	C10—C11—C12—C13	1.2 (6)
O3—C2—C3—C4	−175.3 (3)	C9—N3—C13—C12	0.3 (5)
C1—C2—C3—C4	3.3 (5)	Cu1—N3—C13—C12	−176.2 (3)
C2—C3—C4—C5	−1.4 (6)	C11—C12—C13—N3	−1.1 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O2^i	0.88 (3)	1.94 (1)	2.818 (3)	169 (3)

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