rac-Poly[bis­(μ-tryptophanato)manganese(II)]

In the title compound, [Mn(C₁₁H₁₁N₂O₂)₂]_n, the Mn atom is chelated by the tryptophanate anion through the amino N and carboxylate O atoms; it is also linked to the carbonyl O atom of an adjacent monomer unit, forming a polymeric sheet. The Mn atom lies on an inversion centre.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.066
• wR factor = 0.170
• Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1A    ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N2     -   H2B    ...          ?
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            O1  -MN1 -O1  -C11    14.00  0.00   3.666   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         10
            N2  -MN1 -N2  -C10     2.00  0.00   3.666   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         13
            O2  -MN1 -O2  -C11     2.00  0.00   3.666   1.555   1.555   4.565

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 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
   1 ALERT type 3 Indicator that the structure quality may be low
   3 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: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

rac-Poly[bis(µ-tryptophanato)manganese(II)]

Crystal data

[Mn(C11H11N2O2)2]	F(000) = 478
Mr = 461.38	Dx = 1.520 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8273 reflections
a = 19.874 (4) Å	θ = 3.9–28.4°
b = 5.3600 (11) Å	µ = 0.69 mm^−1
c = 9.5420 (19) Å	T = 293 K
β = 97.41 (3)°	Slice, colorless
V = 1008.0 (4) Å^3	0.30 × 0.30 × 0.10 mm
Z = 2

Data collection

Siemens SMART CCD diffractometer	1728 independent reflections
Radiation source: fine-focus sealed tube	1665 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
φ and ω scans	θmax = 25.0°, θmin = 3.9°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −23→23
Tmin = 0.819, Tmax = 0.934	k = −6→6
5347 measured reflections	l = −11→11

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)] = 0.066	H-atom parameters constrained
wR(F^2) = 0.170	w = 1/[σ^2(Fo^2) + (0.123P)^2 + 0.282P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
1728 reflections	Δρmax = 0.74 e Å^−3
143 parameters	Δρmin = −0.65 e Å^−3
0 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: 0.22 (2)

Special details

Experimental. IR (KBr)/cm^-1: 3401 (s), 3357 (m), 3288 (s), 2908 (m), 1598 (s), 1456 (m), 1417 (s), 1419 (m), 1223 (m), 1092 (m), 1033 (m), 924 (m), 801 (m), 742 (s), 582 (m), 532 (m), 492 (m), 429 (m).

A suitable single-crystal was carefully selected under a polarizing microscope and mounted in a glass capillary. The scattering intensities were collected on an imaging plate diffractometer (SMART CCD, Siemens) equipped with a fine focus sealed tube X-ray source (Mo Kα, λ = 0.71073 Å) operating at 50 kV and 40 mA.

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	0.5000	0.5000	0.0429 (4)
O1	0.47978 (8)	0.2540 (3)	0.66672 (18)	0.0468 (5)
N2	0.41113 (10)	0.6891 (4)	0.5892 (2)	0.0454 (6)
H2A	0.4257	0.8278	0.6369	0.054*
H2B	0.3791	0.7334	0.5181	0.054*
O2	0.42479 (10)	0.2871 (4)	0.3548 (2)	0.0637 (6)
C9	0.32035 (12)	0.3768 (5)	0.6060 (3)	0.0514 (7)
H9A	0.3312	0.3251	0.5141	0.062*
H9B	0.3122	0.2271	0.6584	0.062*
C10	0.38229 (15)	0.5135 (4)	0.6845 (3)	0.0439 (7)
H10A	0.3682	0.6060	0.7644	0.053*
C5	0.14513 (12)	0.6385 (5)	0.5128 (3)	0.0534 (7)
C6	0.19623 (14)	0.4639 (5)	0.4905 (3)	0.0468 (7)
N1	0.17275 (12)	0.7996 (5)	0.6152 (3)	0.0612 (7)
H1A	0.1520	0.9236	0.6477	0.073*
C11	0.43387 (12)	0.3145 (5)	0.7402 (3)	0.0458 (6)
C8	0.23920 (13)	0.7320 (5)	0.6583 (3)	0.0553 (7)
H8A	0.2683	0.8141	0.7274	0.066*
C7	0.25626 (15)	0.5272 (5)	0.5851 (4)	0.0474 (7)
C4	0.18039 (14)	0.2723 (5)	0.3916 (3)	0.0564 (7)
H4A	0.2130	0.1558	0.3745	0.068*
C3	0.07985 (14)	0.6263 (7)	0.4396 (4)	0.0661 (8)
H3A	0.0470	0.7431	0.4549	0.079*
C2	0.11501 (15)	0.2594 (6)	0.3197 (4)	0.0656 (8)
H2C	0.1040	0.1322	0.2545	0.079*
C1	0.06568 (16)	0.4345 (7)	0.3435 (4)	0.0694 (9)
H1B	0.0224	0.4217	0.2938	0.083*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn1	0.0390 (5)	0.0556 (5)	0.0354 (5)	−0.00208 (18)	0.0094 (3)	−0.00102 (17)
O1	0.0431 (9)	0.0563 (11)	0.0422 (10)	0.0059 (7)	0.0101 (7)	0.0050 (7)
N2	0.0374 (10)	0.0516 (11)	0.0468 (12)	0.0019 (8)	0.0043 (8)	0.0013 (9)
O2	0.0478 (10)	0.0947 (15)	0.0514 (12)	−0.0124 (9)	0.0167 (9)	−0.0263 (10)
C9	0.0400 (13)	0.0533 (15)	0.0609 (16)	0.0000 (10)	0.0065 (11)	−0.0011 (11)
C10	0.0362 (13)	0.0574 (16)	0.0390 (16)	0.0037 (9)	0.0077 (11)	0.0014 (9)
C5	0.0409 (13)	0.0595 (16)	0.0611 (16)	0.0035 (11)	0.0120 (11)	0.0059 (12)
C6	0.0337 (13)	0.0552 (14)	0.0528 (17)	0.0006 (9)	0.0107 (11)	0.0067 (11)
N1	0.0481 (13)	0.0622 (14)	0.0747 (17)	0.0105 (10)	0.0134 (11)	−0.0065 (12)
C11	0.0381 (12)	0.0578 (14)	0.0416 (13)	0.0005 (10)	0.0061 (10)	0.0042 (10)
C8	0.0439 (14)	0.0601 (16)	0.0618 (18)	−0.0006 (11)	0.0068 (12)	−0.0016 (12)
C7	0.0366 (14)	0.0550 (15)	0.0518 (18)	−0.0001 (9)	0.0097 (12)	0.0036 (10)
C4	0.0477 (14)	0.0616 (16)	0.0611 (17)	−0.0007 (11)	0.0117 (12)	0.0008 (12)
C3	0.0386 (14)	0.077 (2)	0.083 (2)	0.0088 (13)	0.0099 (13)	0.0118 (17)
C2	0.0564 (17)	0.075 (2)	0.0639 (19)	−0.0122 (14)	0.0026 (13)	−0.0002 (14)
C1	0.0409 (15)	0.085 (2)	0.079 (2)	−0.0082 (15)	−0.0023 (14)	0.0091 (19)

Geometric parameters (Å, º)

Mn1—O1^i	2.1438 (16)	C5—N1	1.365 (4)
Mn1—O1	2.1438 (16)	C5—C3	1.394 (4)
Mn1—O2	2.2186 (19)	C5—C6	1.417 (4)
Mn1—O2^i	2.2186 (19)	C6—C4	1.402 (4)
Mn1—N2	2.293 (2)	C6—C7	1.441 (4)
Mn1—N2^i	2.293 (2)	N1—C8	1.380 (4)
O1—C11	1.263 (3)	N1—H1A	0.8600
N2—C10	1.475 (3)	C11—O2^iii	1.255 (3)
N2—H2A	0.9000	C8—C7	1.367 (4)
N2—H2B	0.9000	C8—H8A	0.9300
O2—C11^ii	1.255 (3)	C4—C2	1.391 (4)
C9—C7	1.499 (4)	C4—H4A	0.9300
C9—C10	1.541 (4)	C3—C1	1.382 (6)
C9—H9A	0.9700	C3—H3A	0.9300
C9—H9B	0.9700	C2—C1	1.397 (5)
C10—C11	1.527 (3)	C2—H2C	0.9300
C10—H10A	0.9800	C1—H1B	0.9300
O1^i—Mn1—O1	180.000 (1)	C11—C10—H10A	109.2
O1^i—Mn1—O2	91.64 (8)	C9—C10—H10A	109.2
O1—Mn1—O2	88.36 (8)	N1—C5—C3	130.6 (3)
O1^i—Mn1—O2^i	88.36 (8)	N1—C5—C6	107.2 (2)
O1—Mn1—O2^i	91.64 (8)	C3—C5—C6	122.2 (3)
O2—Mn1—O2^i	180.0	C4—C6—C5	118.8 (3)
O1^i—Mn1—N2	103.32 (7)	C4—C6—C7	133.6 (3)
O1—Mn1—N2	76.68 (7)	C5—C6—C7	107.5 (3)
O2—Mn1—N2	88.28 (7)	C5—N1—C8	109.1 (2)
O2^i—Mn1—N2	91.72 (7)	C5—N1—H1A	125.4
O1^i—Mn1—N2^i	76.68 (7)	C8—N1—H1A	125.4
O1—Mn1—N2^i	103.32 (7)	O2^iii—C11—O1	124.6 (2)
O2—Mn1—N2^i	91.72 (7)	O2^iii—C11—C10	116.2 (2)
O2^i—Mn1—N2^i	88.28 (7)	O1—C11—C10	119.1 (2)
N2—Mn1—N2^i	180.0	C7—C8—N1	110.5 (3)
C11—O1—Mn1	118.18 (15)	C7—C8—H8A	124.8
C10—N2—Mn1	109.00 (15)	N1—C8—H8A	124.8
C10—N2—H2A	109.9	C8—C7—C6	105.6 (2)
Mn1—N2—H2A	109.9	C8—C7—C9	128.8 (3)
C10—N2—H2B	109.9	C6—C7—C9	125.3 (2)
Mn1—N2—H2B	109.9	C2—C4—C6	118.9 (3)
H2A—N2—H2B	108.3	C2—C4—H4A	120.6
C11^ii—O2—Mn1	127.31 (16)	C6—C4—H4A	120.6
C7—C9—C10	114.9 (2)	C1—C3—C5	117.7 (3)
C7—C9—H9A	108.5	C1—C3—H3A	121.2
C10—C9—H9A	108.5	C5—C3—H3A	121.2
C7—C9—H9B	108.5	C4—C2—C1	121.1 (3)
C10—C9—H9B	108.5	C4—C2—H2C	119.4
H9A—C9—H9B	107.5	C1—C2—H2C	119.4
N2—C10—C11	111.3 (2)	C3—C1—C2	121.4 (3)
N2—C10—C9	110.7 (2)	C3—C1—H1B	119.3
C11—C10—C9	107.19 (19)	C2—C1—H1B	119.3
N2—C10—H10A	109.2
O1^i—Mn1—O1—C11	141 (100)	C6—C5—N1—C8	−0.2 (3)
O2—Mn1—O1—C11	−91.01 (18)	Mn1—O1—C11—O2^iii	−167.0 (2)
O2^i—Mn1—O1—C11	88.99 (18)	Mn1—O1—C11—C10	17.0 (3)
N2—Mn1—O1—C11	−2.39 (18)	N2—C10—C11—O2^iii	156.1 (2)
N2^i—Mn1—O1—C11	177.61 (18)	C9—C10—C11—O2^iii	−82.7 (3)
O1^i—Mn1—N2—C10	167.98 (16)	N2—C10—C11—O1	−27.5 (3)
O1—Mn1—N2—C10	−12.02 (16)	C9—C10—C11—O1	93.7 (3)
O2—Mn1—N2—C10	76.70 (17)	C5—N1—C8—C7	0.2 (3)
O2^i—Mn1—N2—C10	−103.30 (17)	N1—C8—C7—C6	−0.1 (3)
N2^i—Mn1—N2—C10	23 (100)	N1—C8—C7—C9	−173.9 (3)
O1^i—Mn1—O2—C11^ii	54.8 (2)	C4—C6—C7—C8	−178.1 (3)
O1—Mn1—O2—C11^ii	−125.2 (2)	C5—C6—C7—C8	−0.1 (3)
O2^i—Mn1—O2—C11^ii	−16 (52)	C4—C6—C7—C9	−4.0 (5)
N2—Mn1—O2—C11^ii	158.0 (3)	C5—C6—C7—C9	174.0 (3)
N2^i—Mn1—O2—C11^ii	−22.0 (3)	C10—C9—C7—C8	−21.4 (4)
Mn1—N2—C10—C11	22.6 (3)	C10—C9—C7—C6	166.0 (3)
Mn1—N2—C10—C9	−96.47 (19)	C5—C6—C4—C2	−0.4 (4)
C7—C9—C10—N2	−77.6 (3)	C7—C6—C4—C2	177.5 (3)
C7—C9—C10—C11	160.8 (2)	N1—C5—C3—C1	−177.9 (3)
N1—C5—C6—C4	178.6 (2)	C6—C5—C3—C1	0.5 (5)
C3—C5—C6—C4	−0.2 (4)	C6—C4—C2—C1	0.5 (5)
N1—C5—C6—C7	0.2 (3)	C5—C3—C1—C2	−0.4 (5)
C3—C5—C6—C7	−178.5 (3)	C4—C2—C1—C3	−0.2 (5)
C3—C5—N1—C8	178.3 (3)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1/2, z−1/2; (iii) x, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1^iv	0.90	2.51	2.991 (3)	114

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