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metal-organic compounds
In the title complex, [Mo(L)O2(CH3OH)] [H2L is 3-methoxysalicylaldehyde (4-methoxybenzoyl)hydrazone, C16H16N2O4], the Mo atom has a distorted octahedral O5N configuration, defined by two O atoms from oxo groups, two O atoms and one N atom from the tridentate hydrazone ligand, and one O atom from the solvent methanol molecule. The intermolecular O—HN hydrogen bonds form centrosymmetric dimers, which are held in the crystal structure by van der Waals forces.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804026856/cv6399sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804026856/cv6399Isup2.hkl |
CCDC reference: 255471
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.028
- wR factor = 0.074
- Data-to-parameter ratio = 16.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.51 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 1 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 top
Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
(Methanol-κO)[3-methoxysalicylaldehyde
(4-methoxybenzoyl)hydrazonato(2-)-κ3O,O',N]dioxomolybdenum(VI) top
Crystal data top
[Mo(C16H14N2O4)O2(CH4O)] | F(000) = 928 |
Mr = 458.27 | Dx = 1.679 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 10166 reflections |
a = 13.131 (3) Å | θ = 4.0–28.0° |
b = 9.942 (2) Å | µ = 0.77 mm−1 |
c = 15.031 (3) Å | T = 293 K |
β = 112.47 (3)° | Prism, red |
V = 1813.2 (8) Å3 | 0.39 × 0.26 × 0.21 mm |
Z = 4 |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 4109 independent reflections |
Radiation source: fine-focus sealed tube | 3774 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 10 pixels mm-1 | θmax = 27.5°, θmin = 3.3° |
ω scan | h = −17→17 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −12→12 |
Tmin = 0.754, Tmax = 0.856 | l = −19→17 |
16671 measured reflections |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.074 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0413P)2 + 0.8397P] where P = (Fo2 + 2Fc2)/3 |
4109 reflections | (Δ/σ)max = 0.002 |
250 parameters | Δρmax = 0.53 e Å−3 |
1 restraint | Δρmin = −0.30 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Mo1 | 0.631581 (13) | 0.383777 (16) | 0.346081 (12) | 0.03506 (7) | |
O1 | 0.74996 (11) | 0.50887 (13) | 0.40404 (11) | 0.0415 (3) | |
O2 | 0.48477 (11) | 0.30993 (13) | 0.33662 (10) | 0.0395 (3) | |
O3 | 0.93998 (12) | 0.61234 (15) | 0.42123 (14) | 0.0514 (4) | |
O4 | 0.01490 (15) | 0.1363 (2) | 0.31702 (15) | 0.0692 (5) | |
O5 | 0.59264 (14) | 0.42566 (18) | 0.22768 (12) | 0.0510 (4) | |
O6 | 0.69962 (13) | 0.23506 (15) | 0.35995 (13) | 0.0523 (4) | |
O7 | 0.66255 (12) | 0.34127 (15) | 0.51140 (11) | 0.0423 (3) | |
H18 | 0.631 (2) | 0.391 (2) | 0.5376 (19) | 0.064* | |
N1 | 0.53721 (12) | 0.54853 (15) | 0.38195 (11) | 0.0328 (3) | |
N2 | 0.43303 (12) | 0.51264 (16) | 0.37967 (12) | 0.0351 (3) | |
C1 | 0.75727 (15) | 0.64418 (19) | 0.40609 (13) | 0.0337 (4) | |
C2 | 0.85927 (15) | 0.7015 (2) | 0.41603 (14) | 0.0378 (4) | |
C3 | 0.87014 (18) | 0.8404 (2) | 0.41869 (16) | 0.0434 (4) | |
H3 | 0.9366 | 0.8792 | 0.4239 | 0.052* | |
C4 | 0.78206 (19) | 0.9217 (2) | 0.41359 (17) | 0.0474 (5) | |
H4 | 0.7904 | 1.0146 | 0.4156 | 0.057* | |
C5 | 0.68332 (18) | 0.86741 (19) | 0.40572 (16) | 0.0420 (4) | |
H5 | 0.6253 | 0.9234 | 0.4026 | 0.050* | |
C6 | 0.66942 (15) | 0.72660 (19) | 0.40233 (13) | 0.0348 (4) | |
C7 | 0.56445 (15) | 0.67332 (19) | 0.39549 (14) | 0.0355 (4) | |
H7 | 0.5130 | 0.7333 | 0.4013 | 0.043* | |
C8 | 1.04465 (17) | 0.6639 (3) | 0.43132 (18) | 0.0506 (5) | |
H8A | 1.0372 | 0.7176 | 0.3761 | 0.076* | |
H8B | 1.0942 | 0.5906 | 0.4364 | 0.076* | |
H8C | 1.0734 | 0.7184 | 0.4883 | 0.076* | |
C9 | 0.41266 (15) | 0.38709 (18) | 0.35333 (13) | 0.0340 (4) | |
C10 | 0.30693 (15) | 0.3250 (2) | 0.34308 (13) | 0.0352 (4) | |
C11 | 0.21659 (18) | 0.4018 (2) | 0.33759 (18) | 0.0474 (5) | |
H11 | 0.2225 | 0.4951 | 0.3398 | 0.057* | |
C12 | 0.11790 (18) | 0.3430 (3) | 0.32888 (18) | 0.0528 (6) | |
H12 | 0.0582 | 0.3962 | 0.3253 | 0.063* | |
C13 | 0.10840 (18) | 0.2042 (3) | 0.32559 (16) | 0.0490 (5) | |
C14 | 0.1972 (2) | 0.1268 (2) | 0.32934 (19) | 0.0525 (6) | |
H14 | 0.1905 | 0.0336 | 0.3261 | 0.063* | |
C15 | 0.29579 (17) | 0.1854 (2) | 0.33785 (16) | 0.0440 (5) | |
H15 | 0.3548 | 0.1319 | 0.3401 | 0.053* | |
C16 | −0.0781 (2) | 0.2121 (4) | 0.3132 (2) | 0.0847 (11) | |
H16A | −0.0577 | 0.2703 | 0.3682 | 0.127* | |
H16B | −0.1354 | 0.1522 | 0.3133 | 0.127* | |
H16C | −0.1042 | 0.2652 | 0.2555 | 0.127* | |
C17 | 0.6744 (2) | 0.2084 (3) | 0.5490 (2) | 0.0601 (6) | |
H17A | 0.6094 | 0.1573 | 0.5139 | 0.090* | |
H17B | 0.6846 | 0.2117 | 0.6157 | 0.090* | |
H17C | 0.7372 | 0.1664 | 0.5429 | 0.090* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Mo1 | 0.03423 (10) | 0.03001 (11) | 0.04664 (12) | 0.00128 (6) | 0.02184 (8) | −0.00434 (6) |
O1 | 0.0325 (7) | 0.0301 (7) | 0.0626 (9) | 0.0020 (5) | 0.0190 (6) | −0.0008 (6) |
O2 | 0.0366 (7) | 0.0344 (7) | 0.0525 (8) | −0.0018 (5) | 0.0227 (6) | −0.0070 (6) |
O3 | 0.0323 (7) | 0.0454 (9) | 0.0763 (11) | 0.0033 (6) | 0.0206 (7) | 0.0049 (7) |
O4 | 0.0502 (10) | 0.0891 (14) | 0.0721 (12) | −0.0286 (9) | 0.0276 (9) | −0.0043 (10) |
O5 | 0.0543 (9) | 0.0551 (9) | 0.0497 (9) | −0.0069 (7) | 0.0268 (7) | −0.0028 (7) |
O6 | 0.0556 (9) | 0.0359 (8) | 0.0791 (11) | 0.0072 (7) | 0.0410 (8) | −0.0026 (7) |
O7 | 0.0495 (8) | 0.0357 (7) | 0.0471 (8) | 0.0068 (6) | 0.0244 (7) | 0.0001 (6) |
N1 | 0.0297 (7) | 0.0330 (8) | 0.0379 (8) | 0.0018 (6) | 0.0152 (6) | −0.0007 (6) |
N2 | 0.0306 (7) | 0.0353 (8) | 0.0422 (9) | 0.0004 (6) | 0.0173 (6) | −0.0011 (6) |
C1 | 0.0346 (9) | 0.0315 (9) | 0.0351 (9) | 0.0010 (7) | 0.0133 (7) | 0.0017 (7) |
C2 | 0.0345 (9) | 0.0399 (10) | 0.0392 (10) | 0.0009 (8) | 0.0143 (8) | 0.0035 (8) |
C3 | 0.0411 (10) | 0.0406 (11) | 0.0518 (12) | −0.0065 (9) | 0.0213 (9) | 0.0023 (9) |
C4 | 0.0544 (12) | 0.0307 (10) | 0.0623 (14) | −0.0028 (9) | 0.0282 (11) | 0.0013 (9) |
C5 | 0.0461 (11) | 0.0312 (10) | 0.0545 (12) | 0.0041 (8) | 0.0258 (10) | 0.0011 (8) |
C6 | 0.0367 (9) | 0.0335 (9) | 0.0364 (9) | 0.0006 (7) | 0.0162 (8) | −0.0004 (7) |
C7 | 0.0350 (9) | 0.0317 (9) | 0.0427 (10) | 0.0040 (7) | 0.0182 (8) | 0.0007 (7) |
C8 | 0.0329 (10) | 0.0631 (14) | 0.0566 (13) | −0.0020 (10) | 0.0181 (9) | 0.0004 (11) |
C9 | 0.0328 (9) | 0.0375 (10) | 0.0326 (9) | 0.0010 (7) | 0.0135 (7) | −0.0007 (7) |
C10 | 0.0351 (9) | 0.0387 (10) | 0.0336 (9) | −0.0020 (7) | 0.0150 (7) | −0.0029 (7) |
C11 | 0.0375 (10) | 0.0449 (11) | 0.0597 (14) | −0.0035 (8) | 0.0185 (10) | −0.0121 (10) |
C12 | 0.0358 (10) | 0.0638 (15) | 0.0618 (14) | −0.0046 (10) | 0.0221 (10) | −0.0178 (12) |
C13 | 0.0414 (11) | 0.0656 (15) | 0.0423 (11) | −0.0170 (10) | 0.0186 (9) | −0.0048 (10) |
C14 | 0.0528 (13) | 0.0448 (13) | 0.0575 (14) | −0.0118 (10) | 0.0183 (11) | 0.0021 (10) |
C15 | 0.0409 (10) | 0.0409 (11) | 0.0503 (12) | −0.0018 (8) | 0.0177 (9) | −0.0011 (9) |
C16 | 0.0484 (15) | 0.141 (3) | 0.078 (2) | −0.0317 (17) | 0.0392 (14) | −0.027 (2) |
C17 | 0.0729 (16) | 0.0465 (13) | 0.0739 (17) | 0.0196 (12) | 0.0427 (14) | 0.0188 (12) |
Geometric parameters (Å, º) top
Mo1—N1 | 2.2405 (15) | C5—C6 | 1.410 (3) |
Mo1—O1 | 1.9201 (14) | C5—H5 | 0.9300 |
Mo1—O2 | 2.0164 (14) | C6—C7 | 1.443 (3) |
Mo1—O5 | 1.7048 (17) | C7—H7 | 0.9300 |
Mo1—O6 | 1.6985 (15) | C8—H8A | 0.9600 |
Mo1—O7 | 2.3970 (16) | C8—H8B | 0.9600 |
N1—N2 | 1.402 (2) | C8—H8C | 0.9600 |
N1—C7 | 1.286 (3) | C9—C10 | 1.472 (3) |
N2—C9 | 1.306 (2) | C10—C11 | 1.386 (3) |
O1—C1 | 1.348 (2) | C10—C15 | 1.395 (3) |
O2—C9 | 1.315 (2) | C11—C12 | 1.382 (3) |
O3—C2 | 1.361 (2) | C11—H11 | 0.9300 |
O3—C8 | 1.420 (2) | C12—C13 | 1.384 (4) |
O4—C13 | 1.364 (3) | C12—H12 | 0.9300 |
O4—C16 | 1.417 (4) | C13—C14 | 1.381 (4) |
O7—C17 | 1.422 (3) | C14—C15 | 1.380 (3) |
O7—H18 | 0.83 (3) | C14—H14 | 0.9300 |
C1—C6 | 1.398 (3) | C15—H15 | 0.9300 |
C1—C2 | 1.410 (3) | C16—H16A | 0.9600 |
C2—C3 | 1.387 (3) | C16—H16B | 0.9600 |
C3—C4 | 1.389 (3) | C16—H16C | 0.9600 |
C3—H3 | 0.9300 | C17—H17A | 0.9600 |
C4—C5 | 1.367 (3) | C17—H17B | 0.9600 |
C4—H4 | 0.9300 | C17—H17C | 0.9600 |
N1—Mo1—O7 | 76.69 (6) | C3—C2—C1 | 119.25 (18) |
O1—Mo1—N1 | 81.00 (6) | C3—C4—H4 | 119.4 |
O1—Mo1—O2 | 148.67 (6) | C4—C3—H3 | 119.9 |
O1—Mo1—O7 | 81.76 (6) | C4—C5—C6 | 120.02 (19) |
O2—Mo1—N1 | 71.42 (6) | C4—C5—H5 | 120.0 |
O2—Mo1—O7 | 77.75 (6) | C5—C4—C3 | 121.2 (2) |
O5—Mo1—O7 | 171.71 (7) | C5—C4—H4 | 119.4 |
O5—Mo1—N1 | 95.73 (7) | C5—C6—C7 | 118.29 (17) |
O5—Mo1—O1 | 100.56 (8) | C6—C1—C2 | 120.19 (17) |
O5—Mo1—O2 | 96.78 (8) | C6—C5—H5 | 120.0 |
O6—Mo1—N1 | 156.95 (7) | C6—C7—H7 | 117.8 |
O6—Mo1—O1 | 102.21 (7) | C7—N1—Mo1 | 126.70 (12) |
O6—Mo1—O2 | 97.79 (7) | C7—N1—N2 | 117.35 (15) |
O6—Mo1—O5 | 105.94 (8) | C9—N2—N1 | 109.61 (15) |
O6—Mo1—O7 | 81.17 (7) | C9—O2—Mo1 | 120.85 (12) |
Mo1—O7—H18 | 118 (2) | C10—C11—H11 | 119.3 |
N1—C7—C6 | 124.46 (17) | C10—C15—H15 | 120.0 |
N1—C7—H7 | 117.8 | C11—C10—C15 | 118.40 (19) |
N2—N1—Mo1 | 115.62 (11) | C11—C10—C9 | 121.78 (18) |
N2—C9—O2 | 122.44 (17) | C11—C12—C13 | 119.6 (2) |
N2—C9—C10 | 120.51 (17) | C11—C12—H12 | 120.2 |
O1—C1—C6 | 122.23 (17) | C12—C11—C10 | 121.5 (2) |
O1—C1—C2 | 117.53 (17) | C12—C11—H11 | 119.3 |
O2—C9—C10 | 117.03 (16) | C13—O4—C16 | 118.1 (2) |
O3—C2—C3 | 125.28 (19) | C13—C12—H12 | 120.2 |
O3—C2—C1 | 115.47 (18) | C13—C14—H14 | 119.5 |
O3—C8—H8A | 109.5 | C14—C13—C12 | 119.4 (2) |
O3—C8—H8B | 109.5 | C14—C15—C10 | 120.0 (2) |
O3—C8—H8C | 109.5 | C14—C15—H15 | 120.0 |
O4—C13—C14 | 116.3 (2) | C15—C10—C9 | 119.81 (17) |
O4—C13—C12 | 124.2 (2) | C15—C14—C13 | 121.0 (2) |
O4—C16—H16A | 109.5 | C15—C14—H14 | 119.5 |
O4—C16—H16B | 109.5 | C17—O7—Mo1 | 121.70 (14) |
O4—C16—H16C | 109.5 | C17—O7—H18 | 111 (2) |
O7—C17—H17A | 109.5 | H8A—C8—H8B | 109.5 |
O7—C17—H17B | 109.5 | H8A—C8—H8C | 109.5 |
O7—C17—H17C | 109.5 | H8B—C8—H8C | 109.5 |
C1—O1—Mo1 | 134.01 (12) | H16A—C16—H16B | 109.5 |
C1—C6—C5 | 119.13 (18) | H16A—C16—H16C | 109.5 |
C1—C6—C7 | 122.58 (17) | H16B—C16—H16C | 109.5 |
C2—O3—C8 | 118.15 (17) | H17A—C17—H17B | 109.5 |
C2—C3—C4 | 120.2 (2) | H17A—C17—H17C | 109.5 |
C2—C3—H3 | 119.9 | H17B—C17—H17C | 109.5 |
Mo1—N1—N2—C9 | −1.90 (19) | O6—Mo1—N1—N2 | −64.2 (2) |
Mo1—N1—C7—C6 | −8.6 (3) | O6—Mo1—N1—C7 | 122.6 (2) |
Mo1—O1—C1—C6 | 30.9 (3) | O6—Mo1—O1—C1 | 168.72 (18) |
Mo1—O1—C1—C2 | −151.46 (15) | O6—Mo1—O2—C9 | 159.75 (15) |
Mo1—O2—C9—N2 | −2.3 (3) | O6—Mo1—O7—C17 | −26.97 (17) |
Mo1—O2—C9—C10 | 178.97 (12) | O7—Mo1—N1—N2 | −80.64 (12) |
N1—Mo1—O1—C1 | −34.52 (18) | O7—Mo1—N1—C7 | 106.14 (16) |
N1—Mo1—O2—C9 | 0.72 (14) | O7—Mo1—O1—C1 | −112.24 (18) |
N1—Mo1—O7—C17 | 146.58 (18) | O7—Mo1—O2—C9 | 80.60 (14) |
N1—N2—C9—O2 | 2.7 (2) | C1—C2—C3—C4 | 1.3 (3) |
N1—N2—C9—C10 | −178.62 (16) | C1—C6—C7—N1 | −7.7 (3) |
N2—N1—C7—C6 | 178.28 (17) | C2—C1—C6—C5 | 1.9 (3) |
N2—C9—C10—C11 | 15.9 (3) | C2—C1—C6—C7 | −177.86 (18) |
N2—C9—C10—C15 | −164.63 (19) | C2—C3—C4—C5 | −0.1 (4) |
O1—Mo1—N1—N2 | −164.23 (13) | C3—C4—C5—C6 | −0.2 (4) |
O1—Mo1—N1—C7 | 22.55 (16) | C4—C5—C6—C1 | −0.7 (3) |
O1—Mo1—O2—C9 | 30.3 (2) | C4—C5—C6—C7 | 179.1 (2) |
O1—Mo1—O7—C17 | −130.78 (17) | C5—C6—C7—N1 | 172.53 (19) |
O1—C1—C2—C3 | −179.83 (19) | C6—C1—C2—O3 | 178.51 (18) |
O1—C1—C2—O3 | 0.9 (3) | C6—C1—C2—C3 | −2.2 (3) |
O1—C1—C6—C5 | 179.40 (19) | C7—N1—N2—C9 | 171.98 (17) |
O1—C1—C6—C7 | −0.3 (3) | C8—O3—C2—C3 | 0.8 (3) |
O2—Mo1—N1—N2 | 0.70 (12) | C8—O3—C2—C1 | −179.98 (18) |
O2—Mo1—N1—C7 | −172.52 (17) | C9—C10—C11—C12 | −179.4 (2) |
O2—Mo1—O1—C1 | −62.8 (2) | C9—C10—C15—C14 | 179.3 (2) |
O2—Mo1—O7—C17 | 73.06 (17) | C10—C11—C12—C13 | 0.1 (4) |
O2—C9—C10—C11 | −165.34 (19) | C11—C10—C15—C14 | −1.3 (3) |
O2—C9—C10—C15 | 14.1 (3) | C11—C12—C13—O4 | −179.9 (2) |
O3—C2—C3—C4 | −179.5 (2) | C11—C12—C13—C14 | −1.1 (4) |
O4—C13—C14—C15 | 179.9 (2) | C12—C13—C14—C15 | 1.0 (4) |
O5—Mo1—N1—N2 | 95.95 (13) | C13—C14—C15—C10 | 0.2 (4) |
O5—Mo1—N1—C7 | −77.27 (17) | C15—C10—C11—C12 | 1.1 (3) |
O5—Mo1—O1—C1 | 59.69 (19) | C16—O4—C13—C12 | −1.4 (4) |
O5—Mo1—O2—C9 | −93.07 (15) | C16—O4—C13—C14 | 179.8 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H18···N2i | 0.83 (3) | 1.99 (3) | 2.817 (2) | 169 (3) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
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