The title compound, C
24H
18N
4O
4·2H
2O, has a centre of symmetry at the mid-point of the central C—C bond. The uncoordinated water links molecules along the
c axis
via O—H
O hydrogen bonds. N—H
O hydrogen bonds complete a two-dimensional hydrogen-bond network. π–π interactions exist between the imino group and the aromatic ring.
Supporting information
CCDC reference: 208406
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.053
- wR factor = 0.135
- Data-to-parameter ratio = 12.4
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor O3 - H3WA ... ?
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.822 1.000
Tmin(prime) and Tmax expected: 0.979 0.990
RR(prime) = 0.831
Please check that your absorption correction is appropriate.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.83
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.99
PLAT417_ALERT_2_C Short Inter D-H..H-D H3WA .. H2 .. 2.10 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
PLAT737_ALERT_1_C D...A Calc 2.935(3), Rep 2.935(9) ...... 3.00 su-Ra
N2 -O3 1.555 1.555
PLAT737_ALERT_1_C D...A Calc 2.554(3), Rep 2.554(9) ...... 3.00 su-Ra
O1 -N1 1.555 1.555
PLAT737_ALERT_1_C D...A Calc 2.933(4), Rep 2.933(9) ...... 2.25 su-Ra
O3 -O2 1.555 4.566
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
1 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
6 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
2 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEXII (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); 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, 2003); software used to prepare material for publication: SHELXTL.
Bis(2-hydroxy-1-naphthaldehyde) oxaloyldihydrazone dihydrate
top
Crystal data top
C24H18N4O4·2H2O | F(000) = 484 |
Mr = 462.46 | Dx = 1.405 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 649 reflections |
a = 13.678 (4) Å | θ = 2.8–26.3° |
b = 5.9250 (18) Å | µ = 0.10 mm−1 |
c = 14.883 (5) Å | T = 293 K |
β = 114.983 (5)° | Needle, yellow |
V = 1093.3 (6) Å3 | 0.20 × 0.18 × 0.10 mm |
Z = 2 | |
Data collection top
Bruker APEX-II CCD area-detector diffractometer | 1918 independent reflections |
Radiation source: fine-focus sealed tube | 1149 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
φ and ω scans | θmax = 25.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→15 |
Tmin = 0.822, Tmax = 1.000 | k = −3→7 |
5069 measured reflections | l = −17→17 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0569P)2 + 0.2643P] where P = (Fo2 + 2Fc2)/3 |
1918 reflections | (Δ/σ)max = 0.001 |
155 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
Special details top
Experimental. IR (KBr, ν cm-1): 3277, 3199, 1610, 1540, 1407, 1358, 1336, 1272, 1131, 955,
858, 609 (IR spectra were recorded on a BIO-RAD FTS 3000 IR
spectrophotometer). |
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 (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.12945 (16) | 0.4243 (3) | 0.04378 (15) | 0.0398 (6) | |
N2 | 0.07885 (16) | 0.2389 (3) | 0.06101 (15) | 0.0405 (6) | |
H2 | 0.0823 | 0.2123 | 0.1191 | 0.049* | |
O1 | 0.17894 (17) | 0.6733 (4) | −0.07084 (13) | 0.0592 (6) | |
H1 | 0.1481 | 0.5705 | −0.0563 | 0.089* | |
O2 | 0.01142 (15) | 0.1287 (3) | −0.10093 (14) | 0.0513 (5) | |
O3 | 0.1155 (2) | 0.2429 (5) | 0.27006 (17) | 0.1025 (9) | |
H3WA | 0.0685 | 0.3549 | 0.2426 | 0.154* | |
H3WB | 0.0975 | 0.1741 | 0.3114 | 0.154* | |
C1 | 0.2356 (2) | 0.7980 (4) | 0.01065 (19) | 0.0416 (7) | |
C2 | 0.2877 (2) | 0.9913 (5) | −0.0042 (2) | 0.0518 (8) | |
H2A | 0.2825 | 1.0247 | −0.0671 | 0.062* | |
C3 | 0.3451 (2) | 1.1276 (5) | 0.0731 (2) | 0.0507 (8) | |
H3 | 0.3791 | 1.2536 | 0.0621 | 0.061* | |
C4 | 0.3551 (2) | 1.0850 (4) | 0.1701 (2) | 0.0403 (7) | |
C5 | 0.4141 (2) | 1.2294 (5) | 0.2501 (2) | 0.0512 (8) | |
H5 | 0.4462 | 1.3579 | 0.2387 | 0.061* | |
C6 | 0.4251 (2) | 1.1857 (5) | 0.3428 (2) | 0.0603 (9) | |
H6 | 0.4646 | 1.2828 | 0.3946 | 0.072* | |
C7 | 0.3767 (2) | 0.9928 (6) | 0.3605 (2) | 0.0613 (9) | |
H7 | 0.3848 | 0.9614 | 0.4245 | 0.074* | |
C8 | 0.3175 (2) | 0.8499 (5) | 0.28468 (19) | 0.0501 (8) | |
H8 | 0.2855 | 0.7238 | 0.2981 | 0.060* | |
C9 | 0.30387 (19) | 0.8895 (4) | 0.18657 (18) | 0.0367 (6) | |
C10 | 0.24212 (19) | 0.7450 (4) | 0.10432 (18) | 0.0352 (6) | |
C11 | 0.18548 (19) | 0.5491 (4) | 0.11817 (19) | 0.0389 (6) | |
H11 | 0.1900 | 0.5147 | 0.1808 | 0.047* | |
C12 | 0.02400 (19) | 0.1008 (4) | −0.0154 (2) | 0.0382 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0342 (12) | 0.0319 (13) | 0.0505 (13) | −0.0016 (10) | 0.0152 (11) | −0.0051 (11) |
N2 | 0.0413 (13) | 0.0321 (13) | 0.0451 (13) | −0.0036 (10) | 0.0155 (10) | −0.0029 (10) |
O1 | 0.0697 (15) | 0.0626 (15) | 0.0472 (11) | −0.0106 (11) | 0.0265 (10) | −0.0132 (10) |
O2 | 0.0565 (13) | 0.0484 (12) | 0.0491 (12) | −0.0092 (10) | 0.0224 (10) | −0.0050 (9) |
O3 | 0.139 (2) | 0.113 (2) | 0.0717 (16) | −0.0130 (19) | 0.0598 (16) | −0.0087 (15) |
C1 | 0.0402 (16) | 0.0381 (16) | 0.0474 (16) | 0.0051 (13) | 0.0193 (13) | −0.0027 (13) |
C2 | 0.0603 (19) | 0.0475 (19) | 0.0543 (18) | 0.0009 (15) | 0.0308 (16) | 0.0075 (15) |
C3 | 0.0469 (18) | 0.0397 (17) | 0.070 (2) | −0.0045 (13) | 0.0286 (16) | 0.0088 (15) |
C4 | 0.0304 (15) | 0.0308 (15) | 0.0578 (17) | 0.0015 (11) | 0.0168 (13) | 0.0011 (13) |
C5 | 0.0381 (16) | 0.0359 (17) | 0.074 (2) | −0.0052 (12) | 0.0188 (15) | −0.0052 (15) |
C6 | 0.0519 (19) | 0.053 (2) | 0.066 (2) | −0.0118 (15) | 0.0158 (16) | −0.0219 (16) |
C7 | 0.065 (2) | 0.066 (2) | 0.0497 (18) | −0.0144 (17) | 0.0216 (16) | −0.0128 (15) |
C8 | 0.0560 (19) | 0.0470 (18) | 0.0477 (17) | −0.0148 (14) | 0.0222 (14) | −0.0052 (14) |
C9 | 0.0300 (14) | 0.0309 (15) | 0.0478 (16) | 0.0028 (11) | 0.0151 (12) | −0.0010 (12) |
C10 | 0.0343 (15) | 0.0267 (14) | 0.0442 (15) | 0.0027 (11) | 0.0163 (12) | −0.0003 (11) |
C11 | 0.0379 (15) | 0.0343 (15) | 0.0424 (15) | 0.0027 (12) | 0.0149 (13) | −0.0016 (12) |
C12 | 0.0328 (15) | 0.0335 (15) | 0.0453 (16) | 0.0007 (11) | 0.0136 (12) | −0.0036 (13) |
Geometric parameters (Å, º) top
N1—C11 | 1.282 (3) | C4—C5 | 1.411 (4) |
N1—N2 | 1.379 (3) | C4—C9 | 1.427 (3) |
N2—C12 | 1.344 (3) | C5—C6 | 1.348 (4) |
N2—H2 | 0.8600 | C5—H5 | 0.9300 |
O1—C1 | 1.350 (3) | C6—C7 | 1.401 (4) |
O1—H1 | 0.8200 | C6—H6 | 0.9300 |
O2—C12 | 1.221 (3) | C7—C8 | 1.368 (4) |
O3—H3WA | 0.8940 | C7—H7 | 0.9300 |
O3—H3WB | 0.8556 | C8—C9 | 1.411 (4) |
C1—C10 | 1.394 (4) | C8—H8 | 0.9300 |
C1—C2 | 1.415 (4) | C9—C10 | 1.439 (3) |
C2—C3 | 1.352 (4) | C10—C11 | 1.458 (3) |
C2—H2A | 0.9300 | C11—H11 | 0.9300 |
C3—C4 | 1.413 (4) | C12—C12i | 1.525 (5) |
C3—H3 | 0.9300 | | |
| | | |
C11—N1—N2 | 117.6 (2) | C5—C6—C7 | 119.4 (3) |
C12—N2—N1 | 118.2 (2) | C5—C6—H6 | 120.3 |
C12—N2—H2 | 120.9 | C7—C6—H6 | 120.3 |
N1—N2—H2 | 120.9 | C8—C7—C6 | 120.8 (3) |
C1—O1—H1 | 109.5 | C8—C7—H7 | 119.6 |
H3WA—O3—H3WB | 108.2 | C6—C7—H7 | 119.6 |
O1—C1—C10 | 123.0 (2) | C7—C8—C9 | 121.6 (3) |
O1—C1—C2 | 116.0 (2) | C7—C8—H8 | 119.2 |
C10—C1—C2 | 120.9 (2) | C9—C8—H8 | 119.2 |
C3—C2—C1 | 120.0 (3) | C8—C9—C4 | 116.9 (2) |
C3—C2—H2A | 120.0 | C8—C9—C10 | 123.7 (2) |
C1—C2—H2A | 120.0 | C4—C9—C10 | 119.4 (2) |
C2—C3—C4 | 122.2 (3) | C1—C10—C9 | 118.9 (2) |
C2—C3—H3 | 118.9 | C1—C10—C11 | 120.5 (2) |
C4—C3—H3 | 118.9 | C9—C10—C11 | 120.6 (2) |
C5—C4—C3 | 121.9 (3) | N1—C11—C10 | 119.8 (2) |
C5—C4—C9 | 119.6 (3) | N1—C11—H11 | 120.1 |
C3—C4—C9 | 118.5 (2) | C10—C11—H11 | 120.1 |
C6—C5—C4 | 121.6 (3) | O2—C12—N2 | 125.6 (2) |
C6—C5—H5 | 119.2 | O2—C12—C12 | 122.1 (3) |
C4—C5—H5 | 119.2 | N2—C12—C12 | 112.3 (3) |
| | | |
C11—N1—N2—C12 | −177.0 (2) | C5—C4—C9—C10 | 178.9 (2) |
O1—C1—C2—C3 | 179.1 (3) | C3—C4—C9—C10 | −1.2 (3) |
C10—C1—C2—C3 | 0.1 (4) | O1—C1—C10—C9 | −179.5 (2) |
C1—C2—C3—C4 | −0.3 (4) | C2—C1—C10—C9 | −0.6 (4) |
C2—C3—C4—C5 | −179.3 (3) | O1—C1—C10—C11 | −0.7 (4) |
C2—C3—C4—C9 | 0.8 (4) | C2—C1—C10—C11 | 178.2 (2) |
C3—C4—C5—C6 | −178.7 (3) | C8—C9—C10—C1 | −178.8 (2) |
C9—C4—C5—C6 | 1.1 (4) | C4—C9—C10—C1 | 1.1 (3) |
C4—C5—C6—C7 | −0.2 (4) | C8—C9—C10—C11 | 2.4 (4) |
C5—C6—C7—C8 | −0.7 (5) | C4—C9—C10—C11 | −177.6 (2) |
C6—C7—C8—C9 | 0.6 (5) | N2—N1—C11—C10 | 179.0 (2) |
C7—C8—C9—C4 | 0.3 (4) | C1—C10—C11—N1 | 0.1 (4) |
C7—C8—C9—C10 | −179.7 (3) | C9—C10—C11—N1 | 178.9 (2) |
C5—C4—C9—C8 | −1.1 (4) | N1—N2—C12—O2 | −2.7 (4) |
C3—C4—C9—C8 | 178.7 (2) | N1—N2—C12—C12i | 177.9 (2) |
Symmetry code: (i) −x, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O3 | 0.86 | 2.10 | 2.935 (9) | 162 |
O1—H1···N1 | 0.82 | 1.83 | 2.554 (9) | 146 |
O3—H3WB···O2ii | 0.86 | 2.40 | 2.933 (9) | 121 |
Symmetry code: (ii) x, −y+1/2, z+1/2. |