{μ-1,1′-[2-Cyano-2-(2-pyrid­yl)propane-1,3-di­yl]di-η⁵-cyclo­penta­dien­yl}bis­[tricarbonyl­manganese(II)]

The dinuclear title compound, [Mn₂(C₁₉H₁₆N₂)(CO)₆], was isolated en route to other photochromic organometallic targets. The structure features two bridged half-sandwich cyclo­penta­dienylmanganese centers.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.026
• wR factor = 0.070
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O2     -   C22     ..       7.59 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C7     -   C15     ..       8.05 su
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Mn1    -   C21     ..      11.76 su
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Mn1    -   C22     ..      12.83 su
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Mn1    -   C23     ..      10.49 su
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Mn2    -   C24     ..      12.34 su
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Mn2    -   C25     ..      11.56 su
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Mn2    -   C26     ..      11.83 su

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1     -   C21     ..       6.00 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O4     -   C24     ..       5.92 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O5     -   C25     ..       6.88 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O6     -   C26     ..       6.45 su
PLAT432_ALERT_2_C Short Inter X...Y Contact  C3     ..  C3      ..       3.15 Ang.

   0 ALERT level A = In general: serious problem
   8 ALERT level B = Potentially serious problem
   5 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
  13 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
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: PROTEUM2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SADABS (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997), Mercury (Version 1.4.2, Build 2; Macrae et al., 2006) and RASTER3D (Merritt & Bacon, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and publCIF (Westrip, 2007).

{µ-1,1'-[2-Cyano-2-(2-pyridyl)propane-1,3-

Crystal data

[Mn2(C19H16N2)(CO)6]	F(000) = 1112
Mr = 550.28	Dx = 1.593 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 4204 reflections
a = 12.3281 (3) Å	θ = 3.7–69.1°
b = 14.9809 (4) Å	µ = 9.35 mm^−1
c = 12.7137 (3) Å	T = 173 K
β = 102.202 (1)°	Flake, yellow
V = 2295.0 (1) Å^3	0.19 × 0.12 × 0.05 mm
Z = 4

Data collection

Bruker Proteum diffractometer	3998 reflections with I > 2σ(I)
Radiation source: fine-focus rotating anode	Rint = 0.035
area detector scans	θmax = 69.1°, θmin = 3.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −14→14
Tmin = 0.259, Tmax = 0.626	k = −17→17
45918 measured reflections	l = −15→15
4204 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.026	w = 1/[σ^2(Fo^2) + (0.0456P)^2 + 0.8326P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.070	(Δ/σ)max = 0.004
S = 1.05	Δρmax = 0.38 e Å^−3
4204 reflections	Δρmin = −0.22 e Å^−3
316 parameters

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.

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

	x	y	z	Uiso*/Ueq
Mn1	0.09883 (2)	1.048827 (16)	0.759598 (19)	0.01782 (8)
Mn2	0.60923 (2)	0.646565 (17)	1.069138 (19)	0.02019 (9)
N2	0.19326 (11)	0.75748 (9)	0.98444 (11)	0.0214 (3)
O3	0.09187 (12)	1.23885 (8)	0.69833 (11)	0.0355 (3)
C5	0.18953 (15)	1.05683 (11)	0.92285 (13)	0.0219 (3)
H5	0.255	1.0912	0.9459	0.026*
C15	0.39727 (14)	0.93761 (11)	1.05877 (13)	0.0207 (3)
O6	0.52453 (11)	0.60576 (9)	0.83992 (10)	0.0338 (3)
O2	−0.07780 (11)	0.98716 (10)	0.58084 (10)	0.0356 (3)
N1	0.44359 (13)	0.99568 (10)	1.10691 (12)	0.0295 (3)
O4	0.70013 (11)	0.46679 (9)	1.12601 (11)	0.0353 (3)
O1	0.26334 (10)	0.99996 (9)	0.63208 (10)	0.0308 (3)
C9	0.48409 (13)	0.74634 (11)	1.06451 (12)	0.0196 (3)
C16	0.25711 (12)	0.81784 (10)	1.04630 (12)	0.0176 (3)
O5	0.82232 (11)	0.71041 (9)	1.02786 (13)	0.0400 (3)
C12	0.51838 (17)	0.63739 (14)	1.19512 (15)	0.0348 (4)
H12	0.5124	0.5847	1.2351	0.042*
C17	0.25127 (13)	0.83433 (10)	1.15220 (13)	0.0203 (3)
H17	0.2983	0.8775	1.1936	0.024*
C3	0.00626 (14)	1.01612 (12)	0.87900 (13)	0.0248 (3)
H3	−0.0724	1.0181	0.8669	0.03*
C20	0.12117 (14)	0.71178 (11)	1.02880 (14)	0.0243 (3)
H20	0.0758	0.6684	0.9861	0.029*
C6	0.28168 (13)	0.90686 (10)	0.88129 (12)	0.0185 (3)
H6A	0.3369	0.9422	0.8528	0.022*
H6B	0.2556	0.8582	0.8295	0.022*
C4	0.07915 (15)	1.08664 (11)	0.91695 (13)	0.0256 (4)
H4	0.0581	1.1446	0.9356	0.031*
C2	0.07173 (14)	0.94095 (11)	0.86178 (13)	0.0213 (3)
H2	0.0439	0.8839	0.8369	0.026*
C8	0.42794 (13)	0.79769 (10)	0.96717 (12)	0.0197 (3)
H8A	0.3914	0.7552	0.9112	0.024*
H8B	0.4847	0.8308	0.9383	0.024*
C7	0.33956 (13)	0.86505 (10)	0.99082 (12)	0.0178 (3)
C1	0.18495 (14)	0.96590 (10)	0.88808 (12)	0.0188 (3)
C21	0.19983 (13)	1.02098 (11)	0.68092 (13)	0.0217 (3)
C19	0.10913 (14)	0.72431 (11)	1.13369 (14)	0.0247 (3)
H19	0.0563	0.6907	1.1617	0.03*
C18	0.17551 (14)	0.78667 (11)	1.19678 (13)	0.0231 (3)
H18	0.1695	0.7967	1.2691	0.028*
C10	0.58017 (14)	0.77069 (12)	1.14181 (13)	0.0260 (4)
H10	0.6229	0.8232	1.1403	0.031*
C25	0.73928 (15)	0.68487 (11)	1.04440 (15)	0.0276 (4)
C24	0.66504 (14)	0.53646 (12)	1.10247 (14)	0.0257 (4)
C13	0.44572 (14)	0.66325 (12)	1.09892 (14)	0.0250 (4)
H13	0.3822	0.6311	1.063	0.03*
C11	0.60158 (16)	0.70310 (14)	1.22184 (14)	0.0354 (4)
H11	0.6615	0.7023	1.2827	0.043*
C22	−0.01039 (14)	1.01364 (11)	0.64989 (14)	0.0246 (4)
C26	0.55945 (14)	0.61955 (11)	0.92943 (14)	0.0243 (4)
C23	0.09418 (14)	1.16451 (12)	0.71986 (13)	0.0247 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn1	0.02015 (14)	0.01698 (14)	0.01693 (14)	0.00201 (9)	0.00523 (10)	0.00292 (9)
Mn2	0.01968 (14)	0.02329 (15)	0.01825 (14)	0.00462 (9)	0.00551 (10)	0.00351 (10)
N2	0.0246 (7)	0.0191 (6)	0.0202 (7)	−0.0007 (5)	0.0037 (6)	0.0000 (5)
O3	0.0506 (8)	0.0211 (7)	0.0343 (7)	0.0028 (6)	0.0078 (6)	0.0062 (5)
C5	0.0309 (9)	0.0190 (8)	0.0158 (8)	0.0008 (6)	0.0049 (7)	0.0007 (6)
C15	0.0231 (8)	0.0231 (8)	0.0166 (7)	0.0009 (7)	0.0057 (6)	0.0035 (6)
O6	0.0355 (7)	0.0430 (8)	0.0221 (7)	0.0031 (6)	0.0045 (5)	−0.0011 (5)
O2	0.0291 (7)	0.0463 (8)	0.0285 (7)	−0.0085 (6)	−0.0004 (6)	0.0014 (6)
N1	0.0374 (8)	0.0295 (8)	0.0216 (7)	−0.0100 (7)	0.0065 (6)	−0.0036 (6)
O4	0.0366 (7)	0.0300 (7)	0.0420 (8)	0.0097 (6)	0.0143 (6)	0.0122 (6)
O1	0.0285 (6)	0.0397 (7)	0.0274 (6)	0.0050 (5)	0.0127 (5)	0.0056 (5)
C9	0.0197 (7)	0.0217 (8)	0.0187 (8)	0.0039 (6)	0.0071 (6)	−0.0004 (6)
C16	0.0173 (7)	0.0159 (7)	0.0192 (7)	0.0035 (6)	0.0030 (6)	0.0017 (6)
O5	0.0318 (7)	0.0362 (7)	0.0572 (9)	−0.0058 (6)	0.0212 (6)	−0.0046 (7)
C12	0.0418 (11)	0.0400 (10)	0.0289 (10)	0.0186 (9)	0.0214 (8)	0.0149 (8)
C17	0.0216 (8)	0.0190 (7)	0.0197 (8)	0.0023 (6)	0.0032 (6)	−0.0004 (6)
C3	0.0262 (8)	0.0301 (9)	0.0209 (8)	0.0059 (7)	0.0110 (7)	0.0073 (7)
C20	0.0245 (8)	0.0201 (8)	0.0267 (9)	−0.0024 (6)	0.0019 (7)	0.0013 (7)
C6	0.0223 (7)	0.0177 (7)	0.0151 (7)	0.0013 (6)	0.0032 (6)	0.0005 (6)
C4	0.0385 (9)	0.0225 (8)	0.0178 (8)	0.0086 (7)	0.0103 (7)	0.0020 (6)
C2	0.0255 (8)	0.0205 (8)	0.0191 (8)	−0.0001 (6)	0.0076 (6)	0.0048 (6)
C8	0.0211 (7)	0.0209 (8)	0.0181 (7)	0.0024 (6)	0.0063 (6)	0.0019 (6)
C7	0.0203 (7)	0.0168 (7)	0.0160 (7)	0.0002 (6)	0.0031 (6)	−0.0003 (6)
C1	0.0252 (8)	0.0179 (7)	0.0133 (7)	0.0012 (6)	0.0042 (6)	0.0040 (6)
C21	0.0232 (8)	0.0211 (8)	0.0197 (8)	0.0002 (6)	0.0018 (7)	0.0057 (6)
C19	0.0218 (8)	0.0244 (8)	0.0288 (9)	0.0020 (7)	0.0076 (7)	0.0088 (7)
C18	0.0266 (8)	0.0246 (8)	0.0196 (8)	0.0070 (7)	0.0081 (7)	0.0033 (6)
C10	0.0245 (8)	0.0314 (9)	0.0218 (8)	0.0057 (7)	0.0044 (7)	−0.0052 (7)
C25	0.0303 (9)	0.0239 (8)	0.0292 (9)	0.0037 (7)	0.0074 (7)	−0.0010 (7)
C24	0.0230 (8)	0.0315 (9)	0.0240 (8)	0.0011 (7)	0.0079 (7)	0.0034 (7)
C13	0.0237 (8)	0.0256 (8)	0.0295 (9)	0.0061 (7)	0.0142 (7)	0.0066 (7)
C11	0.0366 (10)	0.0519 (12)	0.0171 (8)	0.0205 (9)	0.0042 (7)	0.0014 (8)
C22	0.0250 (8)	0.0258 (8)	0.0251 (9)	0.0010 (7)	0.0099 (7)	0.0066 (7)
C26	0.0216 (8)	0.0251 (8)	0.0278 (9)	0.0046 (7)	0.0088 (7)	0.0038 (7)
C23	0.0287 (8)	0.0252 (9)	0.0199 (8)	0.0020 (7)	0.0046 (7)	0.0019 (7)

Geometric parameters (Å, º)

Mn1—C22	1.8007 (18)	C16—C17	1.386 (2)
Mn1—C23	1.8027 (17)	C16—C7	1.528 (2)
Mn1—C21	1.8032 (17)	O5—C25	1.153 (2)
Mn1—C3	2.1399 (16)	C12—C13	1.409 (3)
Mn1—C4	2.1417 (16)	C12—C11	1.410 (3)
Mn1—C5	2.1428 (16)	C12—H12	0.95
Mn1—C2	2.1434 (16)	C17—C18	1.388 (2)
Mn1—C1	2.1460 (15)	C17—H17	0.95
Mn2—C25	1.7921 (18)	C3—C4	1.405 (3)
Mn2—C26	1.7985 (18)	C3—C2	1.429 (2)
Mn2—C24	1.8030 (18)	C3—H3	0.95
Mn2—C11	2.1384 (18)	C20—C19	1.385 (2)
Mn2—C9	2.1399 (15)	C20—H20	0.95
Mn2—C10	2.1400 (17)	C6—C1	1.502 (2)
Mn2—C13	2.1428 (16)	C6—C7	1.556 (2)
Mn2—C12	2.1440 (18)	C6—H6A	0.99
N2—C20	1.337 (2)	C6—H6B	0.99
N2—C16	1.339 (2)	C4—H4	0.95
O3—C23	1.146 (2)	C2—C1	1.415 (2)
C5—C4	1.419 (2)	C2—H2	0.95
C5—C1	1.430 (2)	C8—C7	1.560 (2)
C5—H5	0.95	C8—H8A	0.99
C15—N1	1.144 (2)	C8—H8B	0.99
C15—C7	1.475 (2)	C19—C18	1.381 (2)
O6—C26	1.147 (2)	C19—H19	0.95
O2—C22	1.145 (2)	C18—H18	0.95
O4—C24	1.145 (2)	C10—C11	1.420 (3)
O1—C21	1.142 (2)	C10—H10	0.95
C9—C10	1.418 (2)	C13—H13	0.95
C9—C13	1.432 (2)	C11—H11	0.95
C9—C8	1.497 (2)
C22—Mn1—C23	95.17 (8)	C16—C17—C18	118.86 (15)
C22—Mn1—C21	89.63 (7)	C16—C17—H17	120.6
C23—Mn1—C21	92.97 (7)	C18—C17—H17	120.6
C22—Mn1—C3	93.38 (7)	C4—C3—C2	107.71 (15)
C23—Mn1—C3	115.39 (7)	C4—C3—Mn1	70.92 (10)
C21—Mn1—C3	151.03 (7)	C2—C3—Mn1	70.64 (9)
C22—Mn1—C4	125.96 (7)	C4—C3—H3	126.1
C23—Mn1—C4	90.25 (7)	C2—C3—H3	126.1
C21—Mn1—C4	143.82 (7)	Mn1—C3—H3	123.9
C3—Mn1—C4	38.30 (7)	N2—C20—C19	123.54 (15)
C22—Mn1—C5	156.69 (7)	N2—C20—H20	118.2
C23—Mn1—C5	101.35 (7)	C19—C20—H20	118.2
C21—Mn1—C5	105.67 (7)	C1—C6—C7	113.90 (12)
C3—Mn1—C5	64.72 (7)	C1—C6—H6A	108.8
C4—Mn1—C5	38.68 (7)	C7—C6—H6A	108.8
C22—Mn1—C2	93.55 (7)	C1—C6—H6B	108.8
C23—Mn1—C2	153.49 (7)	C7—C6—H6B	108.8
C21—Mn1—C2	112.10 (7)	H6A—C6—H6B	107.7
C3—Mn1—C2	38.98 (6)	C3—C4—C5	108.56 (15)
C4—Mn1—C2	64.55 (6)	C3—C4—Mn1	70.78 (9)
C5—Mn1—C2	64.62 (6)	C5—C4—Mn1	70.70 (9)
C22—Mn1—C1	126.07 (7)	C3—C4—H4	125.7
C23—Mn1—C1	138.69 (7)	C5—C4—H4	125.7
C21—Mn1—C1	89.99 (7)	Mn1—C4—H4	124.4
C3—Mn1—C1	65.15 (6)	C1—C2—C3	108.45 (15)
C4—Mn1—C1	65.02 (6)	C1—C2—Mn1	70.84 (9)
C5—Mn1—C1	38.94 (6)	C3—C2—Mn1	70.38 (9)
C2—Mn1—C1	38.53 (6)	C1—C2—H2	125.8
C25—Mn2—C26	91.71 (8)	C3—C2—H2	125.8
C25—Mn2—C24	91.32 (8)	Mn1—C2—H2	124.6
C26—Mn2—C24	93.43 (8)	C9—C8—C7	113.14 (13)
C25—Mn2—C11	104.20 (8)	C9—C8—H8A	109
C26—Mn2—C11	156.13 (7)	C7—C8—H8A	109
C24—Mn2—C11	103.70 (8)	C9—C8—H8B	109
C25—Mn2—C9	115.98 (7)	C7—C8—H8B	109
C26—Mn2—C9	92.09 (7)	H8A—C8—H8B	107.8
C24—Mn2—C9	151.96 (7)	C15—C7—C16	110.88 (13)
C11—Mn2—C9	65.07 (6)	C15—C7—C6	107.51 (12)
C25—Mn2—C10	92.01 (7)	C16—C7—C6	112.06 (12)
C26—Mn2—C10	124.66 (7)	C15—C7—C8	108.64 (13)
C24—Mn2—C10	141.62 (7)	C16—C7—C8	110.45 (12)
C11—Mn2—C10	38.77 (7)	C6—C7—C8	107.14 (12)
C9—Mn2—C10	38.69 (6)	C2—C1—C5	107.29 (14)
C25—Mn2—C13	154.62 (7)	C2—C1—C6	125.90 (14)
C26—Mn2—C13	93.63 (7)	C5—C1—C6	126.80 (15)
C24—Mn2—C13	113.06 (7)	C2—C1—Mn1	70.64 (9)
C11—Mn2—C13	64.52 (7)	C5—C1—Mn1	70.41 (9)
C9—Mn2—C13	39.08 (6)	C6—C1—Mn1	124.63 (10)
C10—Mn2—C13	64.71 (7)	O1—C21—Mn1	177.35 (15)
C25—Mn2—C12	141.22 (8)	C18—C19—C20	118.67 (15)
C26—Mn2—C12	126.89 (8)	C18—C19—H19	120.7
C24—Mn2—C12	89.97 (7)	C20—C19—H19	120.7
C11—Mn2—C12	38.46 (8)	C19—C18—C17	118.55 (15)
C9—Mn2—C12	65.03 (6)	C19—C18—H18	120.7
C10—Mn2—C12	64.64 (7)	C17—C18—H18	120.7
C13—Mn2—C12	38.38 (7)	C9—C10—C11	108.35 (17)
C20—N2—C16	117.29 (14)	C9—C10—Mn2	70.65 (9)
C4—C5—C1	107.98 (15)	C11—C10—Mn2	70.56 (10)
C4—C5—Mn1	70.62 (9)	C9—C10—H10	125.8
C1—C5—Mn1	70.65 (9)	C11—C10—H10	125.8
C4—C5—H5	126	Mn2—C10—H10	124.6
C1—C5—H5	126	O5—C25—Mn2	179.17 (17)
Mn1—C5—H5	124.3	O4—C24—Mn2	178.42 (16)
N1—C15—C7	176.48 (17)	C12—C13—C9	108.28 (16)
C10—C9—C13	107.06 (15)	C12—C13—Mn2	70.86 (10)
C10—C9—C8	127.85 (15)	C9—C13—Mn2	70.35 (9)
C13—C9—C8	125.04 (15)	C12—C13—H13	125.9
C10—C9—Mn2	70.66 (9)	C9—C13—H13	125.9
C13—C9—Mn2	70.57 (9)	Mn2—C13—H13	124.5
C8—C9—Mn2	125.91 (11)	C12—C11—C10	108.03 (16)
N2—C16—C17	123.11 (15)	C12—C11—Mn2	70.99 (11)
N2—C16—C7	114.03 (13)	C10—C11—Mn2	70.67 (10)
C17—C16—C7	122.84 (14)	C12—C11—H11	126
C13—C12—C11	108.28 (16)	C10—C11—H11	126
C13—C12—Mn2	70.77 (10)	Mn2—C11—H11	124
C11—C12—Mn2	70.55 (11)	O2—C22—Mn1	176.67 (16)
C13—C12—H12	125.9	O6—C26—Mn2	176.79 (15)
C11—C12—H12	125.9	O3—C23—Mn1	177.61 (15)
Mn2—C12—H12	124.4