Bis(2-hydr­oxy-1-naphthaldehyde) oxaloyldihydrazone dihydrate

The title compound, C₂₄H₁₈N₄O₄·2H₂O, 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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3	0.20 × 0.18 × 0.10 mm
Z = 2

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0569P)^2 + 0.2643P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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—C12^i	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—C12^i	177.9 (2)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º)

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···O2^ii	0.86	2.40	2.933 (9)	121

Symmetry code: (ii) x, −y+1/2, z+1/2.