Bis(methanol)bis­[(E)-4-meth­oxy-N-(4-pyridylmethyl­ene)aniline]di­thio­cyanatomanganese(II)

The title compound, [Mn(NCS)₂(C₁₃H₁₂N₂O)₂(CH₃OH)₂], has been synthesized and structurally characterized. The Mn atom is located on a crystallographic inversion centre. O—H...N hydrogen bonds connect the Mn^II monomers into a one-dimensional tape structure.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.042
• wR factor = 0.097
• Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    S1     -   C14     ..       7.03 su

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.58 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N3     -   C14     ..       5.23 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14

   0 ALERT level A = In general: serious problem
   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-III (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXTL (Bruker, 1998).

Bis(methanol)bis[(E)-4-methoxy-N-(4- pyridylmethylene)aniline]bis(thiocyanate)manganese(II)

Crystal data

[Mn(NCS)2(C13H12N2O)2(CH4O)2]	F(000) = 686
Mr = 659.70	Dx = 1.323 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.4046 (15) Å	Cell parameters from 2023 reflections
b = 16.724 (3) Å	θ = 2.4–22.8°
c = 12.306 (2) Å	µ = 0.57 mm^−1
β = 106.737 (3)°	T = 294 K
V = 1656.4 (5) Å^3	Block, yellow
Z = 2	0.24 × 0.22 × 0.18 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	3379 independent reflections
Radiation source: fine-focus sealed tube	1963 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
φ and ω scans	θmax = 26.4°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→6
Tmin = 0.876, Tmax = 0.905	k = −20→20
9254 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0302P)^2] where P = (Fo^2 + 2Fc^2)/3
3379 reflections	(Δ/σ)max = 0.002
201 parameters	Δρmax = 0.28 e Å^−3
1 restraint	Δρmin = −0.28 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 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
Mn1	1.0000	0.0000	0.5000	0.03839 (18)
S1	0.56081 (11)	0.08315 (5)	0.16074 (7)	0.0649 (3)
O1	−0.0565 (3)	0.21096 (15)	1.02624 (19)	0.0776 (7)
N1	0.8171 (3)	0.04381 (14)	0.59884 (18)	0.0445 (6)
N2	0.3417 (3)	0.14078 (13)	0.74703 (17)	0.0401 (6)
N3	0.8264 (3)	0.03878 (15)	0.34398 (18)	0.0480 (6)
C1	0.8586 (4)	0.0399 (2)	0.7115 (2)	0.0547 (8)
H1	0.9630	0.0201	0.7499	0.066*
C2	0.7553 (4)	0.06349 (19)	0.7743 (2)	0.0539 (8)
H2	0.7903	0.0590	0.8529	0.065*
C3	0.6009 (3)	0.09353 (16)	0.7211 (2)	0.0406 (7)
C4	0.5575 (4)	0.0991 (2)	0.6047 (2)	0.0673 (10)
H4	0.4547	0.1199	0.5646	0.081*
C5	0.6676 (4)	0.0737 (2)	0.5484 (2)	0.0665 (10)
H5	0.6353	0.0777	0.4697	0.080*
C6	0.4904 (3)	0.11656 (16)	0.7893 (2)	0.0428 (7)
H6	0.5316	0.1132	0.8679	0.051*
C7	0.2435 (3)	0.15646 (16)	0.8217 (2)	0.0382 (6)
C8	0.2543 (3)	0.11038 (17)	0.9169 (2)	0.0450 (7)
H8	0.3283	0.0677	0.9337	0.054*
C9	0.1564 (4)	0.12690 (19)	0.9876 (2)	0.0493 (8)
H9	0.1644	0.0955	1.0513	0.059*
C10	0.0473 (4)	0.19023 (19)	0.9627 (2)	0.0514 (8)
C11	0.0332 (4)	0.23518 (19)	0.8664 (3)	0.0586 (9)
H11	−0.0421	0.2773	0.8487	0.070*
C12	0.1296 (4)	0.21814 (18)	0.7966 (2)	0.0500 (8)
H12	0.1182	0.2485	0.7314	0.060*
C13	−0.0322 (5)	0.1720 (3)	1.1326 (3)	0.0984 (14)
H13A	−0.0582	0.1162	1.1203	0.148*
H13B	−0.1036	0.1956	1.1722	0.148*
H13C	0.0815	0.1779	1.1771	0.148*
C14	0.7160 (3)	0.05750 (16)	0.2674 (2)	0.0388 (7)
O2	1.1193 (2)	0.11962 (12)	0.52743 (15)	0.0491 (5)
H2A	1.189 (3)	0.1257 (18)	0.5888 (14)	0.059*
C15	1.0529 (5)	0.1930 (2)	0.4763 (3)	0.0851 (12)
H15A	1.0131	0.1863	0.3955	0.128*
H15B	1.1379	0.2332	0.4942	0.128*
H15C	0.9627	0.2091	0.5047	0.128*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn1	0.0294 (3)	0.0489 (4)	0.0348 (3)	0.0064 (3)	0.0059 (2)	0.0019 (3)
S1	0.0592 (5)	0.0538 (5)	0.0595 (5)	0.0095 (4)	−0.0181 (4)	0.0007 (4)
O1	0.0803 (17)	0.0912 (19)	0.0812 (16)	0.0310 (14)	0.0551 (15)	0.0109 (13)
N1	0.0343 (13)	0.0573 (16)	0.0432 (13)	0.0078 (12)	0.0132 (11)	0.0048 (12)
N2	0.0415 (14)	0.0397 (14)	0.0419 (12)	0.0028 (11)	0.0163 (11)	−0.0022 (10)
N3	0.0390 (14)	0.0603 (17)	0.0394 (13)	0.0091 (12)	0.0027 (11)	0.0027 (12)
C1	0.0346 (16)	0.082 (2)	0.0463 (17)	0.0125 (16)	0.0097 (14)	0.0027 (16)
C2	0.0406 (17)	0.081 (2)	0.0386 (16)	0.0051 (16)	0.0094 (14)	−0.0034 (15)
C3	0.0348 (16)	0.0436 (18)	0.0458 (16)	−0.0001 (13)	0.0154 (13)	−0.0040 (13)
C4	0.051 (2)	0.106 (3)	0.0475 (18)	0.0340 (19)	0.0183 (16)	0.0123 (18)
C5	0.053 (2)	0.107 (3)	0.0410 (17)	0.032 (2)	0.0157 (16)	0.0085 (17)
C6	0.0416 (17)	0.0476 (18)	0.0397 (15)	−0.0019 (14)	0.0127 (14)	−0.0056 (13)
C7	0.0359 (15)	0.0424 (17)	0.0375 (15)	0.0023 (13)	0.0124 (13)	−0.0040 (13)
C8	0.0384 (16)	0.054 (2)	0.0417 (16)	0.0111 (14)	0.0102 (14)	0.0020 (14)
C9	0.0456 (17)	0.064 (2)	0.0417 (16)	0.0098 (15)	0.0180 (14)	0.0093 (14)
C10	0.0472 (19)	0.059 (2)	0.0543 (18)	0.0074 (16)	0.0248 (16)	−0.0008 (16)
C11	0.059 (2)	0.053 (2)	0.071 (2)	0.0222 (16)	0.0303 (18)	0.0068 (17)
C12	0.0530 (19)	0.048 (2)	0.0530 (17)	0.0110 (15)	0.0212 (16)	0.0093 (14)
C13	0.112 (3)	0.128 (4)	0.081 (3)	0.036 (3)	0.069 (3)	0.018 (2)
C14	0.0416 (17)	0.0359 (17)	0.0400 (15)	0.0010 (13)	0.0134 (14)	−0.0030 (12)
O2	0.0446 (13)	0.0526 (13)	0.0429 (11)	0.0006 (10)	0.0012 (9)	0.0007 (10)
C15	0.092 (3)	0.059 (2)	0.079 (2)	−0.010 (2)	−0.014 (2)	0.0190 (19)

Geometric parameters (Å, º)

Mn1—N3^i	2.150 (2)	C4—H4	0.9300
Mn1—N3	2.150 (2)	C5—H5	0.9300
Mn1—O2^i	2.219 (2)	C6—H6	0.9300
Mn1—O2	2.219 (2)	C7—C12	1.380 (4)
Mn1—N1	2.336 (2)	C7—C8	1.383 (4)
Mn1—N1^i	2.336 (2)	C8—C9	1.387 (4)
S1—C14	1.619 (3)	C8—H8	0.9300
O1—C10	1.373 (3)	C9—C10	1.377 (4)
O1—C13	1.424 (4)	C9—H9	0.9300
N1—C5	1.329 (3)	C10—C11	1.380 (4)
N1—C1	1.330 (3)	C11—C12	1.370 (4)
N2—C6	1.274 (3)	C11—H11	0.9300
N2—C7	1.426 (3)	C12—H12	0.9300
N3—C14	1.159 (3)	C13—H13A	0.9600
C1—C2	1.376 (4)	C13—H13B	0.9600
C1—H1	0.9300	C13—H13C	0.9600
C2—C3	1.369 (4)	O2—C15	1.418 (4)
C2—H2	0.9300	O2—H2A	0.818 (10)
C3—C4	1.376 (4)	C15—H15A	0.9600
C3—C6	1.470 (4)	C15—H15B	0.9600
C4—C5	1.373 (4)	C15—H15C	0.9600
N3^i—Mn1—N3	180.0	N2—C6—H6	118.1
N3^i—Mn1—O2^i	91.41 (8)	C3—C6—H6	118.1
N3—Mn1—O2^i	88.59 (8)	C12—C7—C8	118.6 (3)
N3^i—Mn1—O2	88.59 (8)	C12—C7—N2	119.0 (2)
N3—Mn1—O2	91.41 (8)	C8—C7—N2	122.3 (2)
O2^i—Mn1—O2	179.999 (2)	C7—C8—C9	120.9 (3)
N3^i—Mn1—N1	90.50 (8)	C7—C8—H8	119.5
N3—Mn1—N1	89.50 (8)	C9—C8—H8	119.5
O2^i—Mn1—N1	91.48 (8)	C10—C9—C8	119.4 (3)
O2—Mn1—N1	88.52 (8)	C10—C9—H9	120.3
N3^i—Mn1—N1^i	89.50 (8)	C8—C9—H9	120.3
N3—Mn1—N1^i	90.50 (8)	O1—C10—C9	124.0 (3)
O2^i—Mn1—N1^i	88.52 (8)	O1—C10—C11	116.1 (3)
O2—Mn1—N1^i	91.48 (8)	C9—C10—C11	119.8 (3)
N1—Mn1—N1^i	180.0	C12—C11—C10	120.4 (3)
C10—O1—C13	117.5 (3)	C12—C11—H11	119.8
C5—N1—C1	115.7 (3)	C10—C11—H11	119.8
C5—N1—Mn1	123.40 (18)	C11—C12—C7	120.8 (3)
C1—N1—Mn1	120.86 (19)	C11—C12—H12	119.6
C6—N2—C7	118.5 (2)	C7—C12—H12	119.6
C14—N3—Mn1	170.4 (2)	O1—C13—H13A	109.5
N1—C1—C2	123.6 (3)	O1—C13—H13B	109.5
N1—C1—H1	118.2	H13A—C13—H13B	109.5
C2—C1—H1	118.2	O1—C13—H13C	109.5
C3—C2—C1	120.1 (3)	H13A—C13—H13C	109.5
C3—C2—H2	120.0	H13B—C13—H13C	109.5
C1—C2—H2	120.0	N3—C14—S1	179.5 (3)
C2—C3—C4	116.9 (3)	C15—O2—Mn1	127.58 (18)
C2—C3—C6	119.4 (2)	C15—O2—H2A	113 (2)
C4—C3—C6	123.7 (3)	Mn1—O2—H2A	115 (2)
C5—C4—C3	119.3 (3)	O2—C15—H15A	109.5
C5—C4—H4	120.4	O2—C15—H15B	109.5
C3—C4—H4	120.4	H15A—C15—H15B	109.5
N1—C5—C4	124.4 (3)	O2—C15—H15C	109.5
N1—C5—H5	117.8	H15A—C15—H15C	109.5
C4—C5—H5	117.8	H15B—C15—H15C	109.5
N2—C6—C3	123.8 (2)
N3^i—Mn1—N1—C5	−176.6 (3)	C4—C3—C6—N2	3.0 (5)
N3—Mn1—N1—C5	3.4 (3)	C6—N2—C7—C12	145.5 (3)
O2^i—Mn1—N1—C5	−85.1 (3)	C6—N2—C7—C8	−36.6 (4)
O2—Mn1—N1—C5	94.9 (3)	C12—C7—C8—C9	−1.8 (4)
N3^i—Mn1—N1—C1	3.4 (2)	N2—C7—C8—C9	−179.7 (2)
N3—Mn1—N1—C1	−176.6 (2)	C7—C8—C9—C10	−0.2 (4)
O2^i—Mn1—N1—C1	94.8 (2)	C13—O1—C10—C9	9.5 (5)
O2—Mn1—N1—C1	−85.2 (2)	C13—O1—C10—C11	−173.0 (3)
C5—N1—C1—C2	1.0 (5)	C8—C9—C10—O1	179.1 (3)
Mn1—N1—C1—C2	−178.9 (2)	C8—C9—C10—C11	1.7 (5)
N1—C1—C2—C3	−0.5 (5)	O1—C10—C11—C12	−178.9 (3)
C1—C2—C3—C4	−0.6 (5)	C9—C10—C11—C12	−1.3 (5)
C1—C2—C3—C6	178.4 (3)	C10—C11—C12—C7	−0.7 (5)
C2—C3—C4—C5	1.0 (5)	C8—C7—C12—C11	2.2 (4)
C6—C3—C4—C5	−178.0 (3)	N2—C7—C12—C11	−179.8 (3)
C1—N1—C5—C4	−0.6 (5)	N3^i—Mn1—O2—C15	−161.5 (3)
Mn1—N1—C5—C4	179.4 (3)	N3—Mn1—O2—C15	18.5 (3)
C3—C4—C5—N1	−0.4 (6)	N1—Mn1—O2—C15	−71.0 (3)
C7—N2—C6—C3	176.0 (2)	N1^i—Mn1—O2—C15	109.0 (3)
C2—C3—C6—N2	−175.9 (3)

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N2^ii	0.82 (1)	2.02 (1)	2.831 (3)	174 (3)

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