Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806030364/ng2063sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806030364/ng2063Isup2.hkl |
CCDC reference: 621422
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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.
[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) Å3 | 0.30 × 0.30 × 0.10 mm |
Z = 2 |
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 on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.066 | H-atom parameters constrained |
wR(F2) = 0.170 | w = 1/[σ2(Fo2) + (0.123P)2 + 0.282P] where P = (Fo2 + 2Fc2)/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+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.22 (2) |
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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
Mn1—O1i | 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—O2i | 2.2186 (19) | C6—C4 | 1.402 (4) |
Mn1—N2 | 2.293 (2) | C6—C7 | 1.441 (4) |
Mn1—N2i | 2.293 (2) | N1—C8 | 1.380 (4) |
O1—C11 | 1.263 (3) | N1—H1A | 0.8600 |
N2—C10 | 1.475 (3) | C11—O2iii | 1.255 (3) |
N2—H2A | 0.9000 | C8—C7 | 1.367 (4) |
N2—H2B | 0.9000 | C8—H8A | 0.9300 |
O2—C11ii | 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 |
O1i—Mn1—O1 | 180.000 (1) | C11—C10—H10A | 109.2 |
O1i—Mn1—O2 | 91.64 (8) | C9—C10—H10A | 109.2 |
O1—Mn1—O2 | 88.36 (8) | N1—C5—C3 | 130.6 (3) |
O1i—Mn1—O2i | 88.36 (8) | N1—C5—C6 | 107.2 (2) |
O1—Mn1—O2i | 91.64 (8) | C3—C5—C6 | 122.2 (3) |
O2—Mn1—O2i | 180.0 | C4—C6—C5 | 118.8 (3) |
O1i—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) |
O2i—Mn1—N2 | 91.72 (7) | C5—N1—H1A | 125.4 |
O1i—Mn1—N2i | 76.68 (7) | C8—N1—H1A | 125.4 |
O1—Mn1—N2i | 103.32 (7) | O2iii—C11—O1 | 124.6 (2) |
O2—Mn1—N2i | 91.72 (7) | O2iii—C11—C10 | 116.2 (2) |
O2i—Mn1—N2i | 88.28 (7) | O1—C11—C10 | 119.1 (2) |
N2—Mn1—N2i | 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 |
C11ii—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 | ||
O1i—Mn1—O1—C11 | 141 (100) | C6—C5—N1—C8 | −0.2 (3) |
O2—Mn1—O1—C11 | −91.01 (18) | Mn1—O1—C11—O2iii | −167.0 (2) |
O2i—Mn1—O1—C11 | 88.99 (18) | Mn1—O1—C11—C10 | 17.0 (3) |
N2—Mn1—O1—C11 | −2.39 (18) | N2—C10—C11—O2iii | 156.1 (2) |
N2i—Mn1—O1—C11 | 177.61 (18) | C9—C10—C11—O2iii | −82.7 (3) |
O1i—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) |
O2i—Mn1—N2—C10 | −103.30 (17) | N1—C8—C7—C6 | −0.1 (3) |
N2i—Mn1—N2—C10 | 23 (100) | N1—C8—C7—C9 | −173.9 (3) |
O1i—Mn1—O2—C11ii | 54.8 (2) | C4—C6—C7—C8 | −178.1 (3) |
O1—Mn1—O2—C11ii | −125.2 (2) | C5—C6—C7—C8 | −0.1 (3) |
O2i—Mn1—O2—C11ii | −16 (52) | C4—C6—C7—C9 | −4.0 (5) |
N2—Mn1—O2—C11ii | 158.0 (3) | C5—C6—C7—C9 | 174.0 (3) |
N2i—Mn1—O2—C11ii | −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. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1iv | 0.90 | 2.51 | 2.991 (3) | 114 |
Symmetry code: (iv) −x+1, y+1/2, −z+3/2. |
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