cis-Di­chlorobis­[N-(3-chloro­phenyl)­pyridine-2-carbox­amide]­manganese(II)

In the title complex, [MnCl₂(C₁₂H₉ClN₂O)₂], the Mn atom is located on a twofold axes and the asymmetric unit thus contains only one-half of the complex; it is built up from one Cl atom and one 2-pyridine­dicarbox­amide ligand bonded to the metal through the carbonyl O and pyridine N atoms.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.037
• wR factor = 0.105
• Data-to-parameter ratio = 18.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Mn1    -   N1       =       5.86 su
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         O1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   2 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

---

Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SHELXTL-NT (Siemens, 1995); 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.

cis-DichloroBis[N-(3-chlorophenyl)pyridine-2-carboxamide]manganese(II)

Crystal data

[MnCl2(C12H9ClN2O)2]	F(000) = 1196
Mr = 591.16	Dx = 1.552 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 4832 reflections
a = 13.181 (4) Å	θ = 1.5–27.5°
b = 9.738 (3) Å	µ = 0.97 mm^−1
c = 19.707 (6) Å	T = 294 K
V = 2529.6 (12) Å^3	Box, yellow
Z = 4	0.28 × 0.24 × 0.2 mm

Data collection

Siemens SMART CCD area-detector diffractometer	2924 independent reflections
Radiation source: fine-focus sealed tube	2076 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 27.6°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→10
Tmin = 0.772, Tmax = 0.829	k = −12→12
16055 measured reflections	l = −23→25

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.105	w = 1/[σ^2(Fo^2) + (0.05P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
2924 reflections	Δρmax = 0.46 e Å^−3
159 parameters	Δρmin = −0.30 e Å^−3

Special details

Experimental. ? #Insert any special details here.

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	0.5000	0.14779 (4)	0.7500	0.04223 (11)
Cl1	0.53667 (3)	0.30940 (5)	0.65726 (2)	0.05043 (13)
Cl2	0.79788 (6)	−0.47714 (6)	0.47450 (3)	0.07830 (19)
O1	0.57090 (9)	−0.02327 (14)	0.69301 (8)	0.0598 (4)
N1	0.66481 (10)	0.12703 (14)	0.78397 (8)	0.0403 (3)
N2	0.71326 (11)	−0.13104 (14)	0.65794 (7)	0.0425 (4)
H2	0.7771	−0.1397	0.6660	0.051*
C1	0.70914 (14)	0.2057 (2)	0.83029 (10)	0.0478 (5)
H1	0.6688	0.2646	0.8559	0.057*
C2	0.81198 (15)	0.2042 (2)	0.84218 (11)	0.0560 (5)
H2A	0.8405	0.2610	0.8750	0.067*
C3	0.87120 (15)	0.1177 (2)	0.80497 (12)	0.0619 (6)
H3	0.9409	0.1146	0.8120	0.074*
C4	0.82650 (13)	0.0349 (2)	0.75686 (11)	0.0559 (5)
H4	0.8656	−0.0253	0.7312	0.067*
C5	0.72325 (12)	0.04220 (17)	0.74719 (9)	0.0382 (4)
C6	0.66340 (13)	−0.04102 (17)	0.69670 (9)	0.0408 (4)
C7	0.67341 (13)	−0.21423 (17)	0.60492 (9)	0.0429 (4)
C8	0.57298 (15)	−0.2118 (2)	0.58419 (11)	0.0592 (6)
H8	0.5261	−0.1567	0.6066	0.071*
C9	0.54332 (18)	−0.2919 (3)	0.53012 (12)	0.0726 (7)
H9	0.4759	−0.2896	0.5162	0.087*
C10	0.60988 (19)	−0.3745 (2)	0.49639 (12)	0.0688 (7)
H10	0.5887	−0.4281	0.4600	0.083*
C11	0.70928 (17)	−0.37620 (19)	0.51777 (10)	0.0536 (5)
C12	0.74213 (15)	−0.29779 (18)	0.57163 (10)	0.0477 (5)
H12	0.8096	−0.3010	0.5854	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn1	0.02083 (18)	0.0482 (2)	0.0576 (2)	0.000	−0.00128 (16)	0.000
Cl1	0.0326 (2)	0.0715 (3)	0.0472 (3)	−0.0112 (2)	0.00021 (18)	0.0017 (2)
Cl2	0.1166 (5)	0.0600 (3)	0.0583 (4)	0.0179 (3)	−0.0022 (3)	−0.0098 (3)
O1	0.0278 (6)	0.0600 (8)	0.0917 (10)	0.0033 (6)	−0.0099 (7)	−0.0236 (7)
N1	0.0279 (7)	0.0453 (8)	0.0477 (8)	0.0042 (6)	−0.0016 (6)	−0.0009 (7)
N2	0.0288 (7)	0.0482 (8)	0.0504 (9)	0.0021 (6)	−0.0055 (6)	−0.0052 (7)
C1	0.0338 (10)	0.0578 (11)	0.0517 (11)	0.0092 (8)	−0.0050 (8)	−0.0101 (9)
C2	0.0388 (11)	0.0660 (13)	0.0631 (13)	0.0046 (9)	−0.0119 (9)	−0.0165 (10)
C3	0.0279 (10)	0.0761 (13)	0.0817 (15)	0.0042 (9)	−0.0091 (9)	−0.0245 (12)
C4	0.0301 (9)	0.0620 (12)	0.0756 (14)	0.0082 (8)	−0.0037 (9)	−0.0200 (10)
C5	0.0271 (8)	0.0369 (8)	0.0505 (10)	0.0018 (7)	−0.0021 (7)	0.0022 (7)
C6	0.0314 (9)	0.0375 (9)	0.0536 (11)	0.0012 (7)	−0.0021 (8)	0.0022 (8)
C7	0.0413 (10)	0.0428 (9)	0.0445 (10)	−0.0076 (8)	−0.0039 (8)	0.0048 (8)
C8	0.0392 (11)	0.0798 (14)	0.0587 (13)	−0.0088 (10)	−0.0034 (9)	−0.0074 (11)
C9	0.0491 (13)	0.1000 (18)	0.0686 (15)	−0.0211 (13)	−0.0102 (11)	−0.0110 (13)
C10	0.0804 (16)	0.0716 (14)	0.0545 (13)	−0.0269 (12)	−0.0077 (12)	−0.0085 (11)
C11	0.0739 (14)	0.0431 (10)	0.0439 (11)	−0.0032 (9)	−0.0052 (10)	0.0034 (8)
C12	0.0509 (11)	0.0434 (9)	0.0490 (11)	0.0028 (8)	−0.0082 (9)	0.0030 (8)

Geometric parameters (Å, º)

Mn1—O1	2.2158 (14)	C3—H3	0.9300
Mn1—N1	2.2821 (15)	C4—C5	1.376 (2)
Mn1—Cl1	2.4598 (7)	C4—H4	0.9300
Cl2—C11	1.748 (2)	C5—C6	1.506 (2)
O1—C6	1.234 (2)	C7—C12	1.383 (3)
N1—C1	1.327 (2)	C7—C8	1.385 (3)
N1—C5	1.342 (2)	C8—C9	1.377 (3)
N2—C6	1.336 (2)	C8—H8	0.9300
N2—C7	1.423 (2)	C9—C10	1.363 (3)
N2—H2	0.8600	C9—H9	0.9300
C1—C2	1.376 (3)	C10—C11	1.376 (3)
C1—H1	0.9300	C10—H10	0.9300
C2—C3	1.363 (3)	C11—C12	1.377 (3)
C2—H2A	0.9300	C12—H12	0.9300
C3—C4	1.377 (3)
O1^i—Mn1—O1	82.50 (8)	C5—C4—H4	120.4
O1—Mn1—N1^i	100.73 (5)	C3—C4—H4	120.4
O1—Mn1—N1	71.38 (5)	N1—C5—C4	121.65 (17)
N1^i—Mn1—N1	169.84 (7)	N1—C5—C6	112.79 (14)
O1—Mn1—Cl1^i	160.13 (4)	C4—C5—C6	125.56 (16)
N1—Mn1—Cl1^i	91.47 (4)	O1—C6—N2	122.99 (16)
O1—Mn1—Cl1	91.24 (5)	O1—C6—C5	118.77 (15)
N1—Mn1—Cl1	95.03 (4)	N2—C6—C5	118.24 (15)
Cl1^i—Mn1—Cl1	100.44 (4)	C12—C7—C8	119.72 (18)
C6—O1—Mn1	119.49 (11)	C12—C7—N2	116.21 (16)
C1—N1—C5	118.31 (15)	C8—C7—N2	124.03 (17)
C1—N1—Mn1	124.72 (12)	C9—C8—C7	119.3 (2)
C5—N1—Mn1	116.26 (11)	C9—C8—H8	120.3
C6—N2—C7	127.75 (15)	C7—C8—H8	120.3
C6—N2—H2	116.1	C10—C9—C8	121.9 (2)
C7—N2—H2	116.1	C10—C9—H9	119.0
N1—C1—C2	122.98 (17)	C8—C9—H9	119.0
N1—C1—H1	118.5	C9—C10—C11	118.1 (2)
C2—C1—H1	118.5	C9—C10—H10	121.0
C3—C2—C1	118.66 (19)	C11—C10—H10	121.0
C3—C2—H2A	120.7	C10—C11—C12	121.9 (2)
C1—C2—H2A	120.7	C10—C11—Cl2	119.56 (17)
C2—C3—C4	119.17 (18)	C12—C11—Cl2	118.53 (17)
C2—C3—H3	120.4	C11—C12—C7	119.07 (19)
C4—C3—H3	120.4	C11—C12—H12	120.5
C5—C4—C3	119.21 (18)	C7—C12—H12	120.5

Symmetry code: (i) −x+1, y, −z+3/2.