Bis(2-methyl-1H-indole-3-carbaldehyde 4-hydroxy­benzoyl­hydrazonato-κ²N,O)nickel(II) N,N-dimethyl­formamide disolvate dihydrate

The title compound, [Ni(C₁₇H₁₄N₃O₂)₂]·2C₃H₇NO·2H₂O, contains Ni^II cations (site symmetry ) chelated by two depro­ton­ated Schiff bases in a trans-NiN₂O₂ square-planar geometry. The complex mol­ecule and the dimethyl­formamide (DMF) and water mol­ecules inter­act by way of O—H...O and N—H...O hydrogen bonds, resulting in a layered structure.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.038
• wR factor = 0.107
• Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   N2      ..       5.72 su
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N4
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          9
            N2  -NI1 -N2  -N1      6.00  0.00   2.666   1.555   1.555   1.555
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              O2   -H2O     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              O2   -H2O     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.85(3), Rep   1.850(10) ......       3.00 su-Ra
              H2O  -O1W     1.555   2.765

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

   6 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEXII (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.

Bis(2-methyl-1H-indole-3-carbaldehyde 4-hydroxybenzoylhydrazonato-κ²N,O)nickel(II) N,N-dimethylformamide disolvate dihydrate

Crystal data

[Ni(C17H14N3O2)2]·2C3H7NO·2H2O	Z = 1
Mr = 825.56	F(000) = 434
Triclinic, P1	Dx = 1.325 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2441 (6) Å	Cell parameters from 3608 reflections
b = 12.326 (1) Å	θ = 2.7–27.1°
c = 12.395 (1) Å	µ = 0.53 mm^−1
α = 76.336 (1)°	T = 295 K
β = 74.120 (1)°	Irregular block, red
γ = 86.253 (1)°	0.45 × 0.35 × 0.15 mm
V = 1034.5 (2) Å^3

Data collection

Bruker APEX-II CCD diffractometer	4495 independent reflections
Radiation source: fine-focus sealed tube	3822 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
ω scans	θmax = 27.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.801, Tmax = 0.925	k = −15→15
9651 measured reflections	l = −15→15

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)] = 0.038	Hydrogen site location: difmap and geom
wR(F^2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0595P)^2 + 0.185P] where P = (Fo^2 + 2Fc^2)/3
4495 reflections	(Δ/σ)max = 0.001
278 parameters	Δρmax = 0.29 e Å^−3
4 restraints	Δρmin = −0.20 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ni1	0.5000	0.5000	0.5000	0.0349 (1)
O1	0.5708 (2)	0.4751 (1)	0.3541 (1)	0.0402 (3)
O2	0.8370 (3)	0.5232 (2)	−0.1833 (1)	0.0681 (5)
O3	0.8506 (2)	0.1739 (1)	0.5398 (1)	0.0536 (4)
O1W	0.9006 (3)	0.3339 (2)	0.3372 (1)	0.0652 (5)
N1	0.6373 (2)	0.6633 (1)	0.3030 (1)	0.0399 (4)
N2	0.5809 (2)	0.6450 (1)	0.4241 (1)	0.0370 (3)
N3	0.7667 (3)	1.0003 (1)	0.4428 (2)	0.0481 (4)
N4	0.8494 (3)	0.2488 (2)	0.6909 (2)	0.0590 (5)
C1	0.6833 (3)	0.5601 (2)	0.1543 (2)	0.0386 (4)
C2	0.6589 (3)	0.4595 (2)	0.1271 (2)	0.0463 (5)
C3	0.7124 (3)	0.4491 (2)	0.0142 (2)	0.0541 (5)
C4	0.7904 (3)	0.5381 (2)	−0.0739 (2)	0.0485 (5)
C5	0.8148 (3)	0.6392 (2)	−0.0486 (2)	0.0526 (5)
C6	0.7616 (3)	0.6493 (2)	0.0648 (2)	0.0496 (5)
C7	0.6279 (3)	0.5683 (1)	0.2759 (2)	0.0366 (4)
C8	0.5984 (3)	0.7255 (1)	0.4719 (2)	0.0385 (4)
C9	0.6632 (3)	0.8387 (1)	0.4276 (2)	0.0385 (4)
C10	0.7043 (3)	0.8969 (2)	0.5019 (2)	0.0413 (4)
C11	0.6951 (3)	0.8610 (2)	0.6272 (2)	0.0544 (5)
C12	0.7671 (3)	1.0150 (2)	0.3292 (2)	0.0474 (5)
C13	0.8188 (4)	1.1089 (2)	0.2393 (2)	0.0674 (7)
C14	0.8003 (5)	1.1028 (2)	0.1338 (2)	0.0880 (10)
C15	0.7319 (5)	1.0061 (2)	0.1179 (2)	0.0863 (10)
C16	0.6818 (4)	0.9130 (2)	0.2070 (2)	0.0625 (6)
C17	0.7015 (3)	0.9149 (2)	0.3149 (2)	0.0438 (4)
C18	0.8306 (3)	0.1669 (2)	0.6431 (2)	0.0547 (5)
C19	0.8989 (4)	0.3612 (2)	0.6225 (2)	0.0692 (7)
C20	0.8215 (6)	0.2320 (3)	0.8135 (2)	0.1060 (12)
H2o	0.910 (4)	0.5731 (18)	−0.232 (2)	0.088 (10)*
H1w1	0.798 (2)	0.371 (2)	0.343 (2)	0.069 (8)*
H1w2	0.902 (4)	0.293 (2)	0.402 (1)	0.082 (9)*
H3n	0.796 (3)	1.048 (2)	0.476 (2)	0.066 (7)*
H2	0.6059	0.3987	0.1857	0.056*
H3	0.6956	0.3813	−0.0024	0.065*
H5	0.8666	0.6999	−0.1076	0.063*
H6	0.7787	0.7172	0.0811	0.060*
H8	0.5609	0.7053	0.5520	0.046*
H11a	0.8227	0.8486	0.6363	0.082*
H11b	0.6225	0.7931	0.6601	0.082*
H11c	0.6341	0.9182	0.6656	0.082*
H13	0.8640	1.1731	0.2504	0.081*
H14	0.8339	1.1639	0.0719	0.106*
H15	0.7197	1.0043	0.0456	0.104*
H16	0.6353	0.8495	0.1949	0.075*
H18	0.7992	0.0971	0.6921	0.066*
H19a	0.9576	0.3585	0.5437	0.104*
H19b	0.9870	0.3933	0.6517	0.104*
H19c	0.7847	0.4060	0.6270	0.104*
H20a	0.7939	0.1548	0.8496	0.159*
H20b	0.7161	0.2771	0.8441	0.159*
H20c	0.9360	0.2530	0.8282	0.159*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0462 (2)	0.02738 (17)	0.02759 (17)	−0.00525 (13)	−0.00232 (13)	−0.00707 (12)
O1	0.0574 (8)	0.0289 (6)	0.0296 (6)	−0.0071 (5)	−0.0023 (6)	−0.0065 (5)
O2	0.0886 (13)	0.0797 (12)	0.0342 (8)	−0.0206 (10)	0.0003 (8)	−0.0234 (8)
O3	0.0742 (10)	0.0443 (8)	0.0460 (8)	−0.0018 (7)	−0.0164 (7)	−0.0163 (6)
O1W	0.0779 (12)	0.0563 (10)	0.0456 (9)	0.0104 (9)	−0.0011 (9)	−0.0020 (8)
N1	0.0561 (10)	0.0320 (7)	0.0278 (7)	−0.0068 (7)	−0.0035 (7)	−0.0067 (6)
N2	0.0455 (9)	0.0322 (7)	0.0301 (7)	−0.0045 (6)	−0.0032 (6)	−0.0079 (6)
N3	0.0605 (11)	0.0329 (8)	0.0518 (10)	−0.0080 (7)	−0.0093 (8)	−0.0158 (7)
N4	0.0706 (12)	0.0652 (12)	0.0491 (11)	0.0054 (10)	−0.0183 (9)	−0.0270 (9)
C1	0.0453 (10)	0.0381 (9)	0.0310 (9)	−0.0043 (8)	−0.0067 (8)	−0.0079 (7)
C2	0.0651 (13)	0.0376 (10)	0.0342 (10)	−0.0069 (9)	−0.0081 (9)	−0.0082 (8)
C3	0.0759 (15)	0.0457 (11)	0.0430 (11)	−0.0070 (10)	−0.0112 (10)	−0.0180 (9)
C4	0.0541 (12)	0.0609 (12)	0.0310 (9)	−0.0059 (10)	−0.0057 (9)	−0.0166 (9)
C5	0.0669 (14)	0.0509 (12)	0.0335 (10)	−0.0171 (10)	−0.0018 (9)	−0.0059 (8)
C6	0.0671 (13)	0.0427 (10)	0.0351 (10)	−0.0146 (9)	−0.0023 (9)	−0.0102 (8)
C7	0.0420 (10)	0.0340 (9)	0.0306 (9)	−0.0027 (7)	−0.0047 (7)	−0.0064 (7)
C8	0.0474 (10)	0.0332 (9)	0.0323 (9)	−0.0045 (7)	−0.0034 (8)	−0.0097 (7)
C9	0.0453 (10)	0.0328 (9)	0.0349 (9)	−0.0040 (7)	−0.0037 (8)	−0.0100 (7)
C10	0.0456 (10)	0.0337 (9)	0.0435 (10)	−0.0025 (8)	−0.0056 (8)	−0.0132 (8)
C11	0.0742 (15)	0.0474 (12)	0.0441 (11)	−0.0046 (10)	−0.0129 (10)	−0.0176 (9)
C12	0.0587 (12)	0.0335 (9)	0.0468 (11)	−0.0060 (8)	−0.0064 (9)	−0.0101 (8)
C13	0.0954 (19)	0.0378 (11)	0.0606 (15)	−0.0182 (11)	−0.0068 (13)	−0.0066 (10)
C14	0.151 (3)	0.0427 (13)	0.0558 (15)	−0.0262 (15)	−0.0136 (17)	0.0086 (11)
C15	0.158 (3)	0.0533 (14)	0.0456 (13)	−0.0178 (17)	−0.0296 (16)	−0.0003 (11)
C16	0.1036 (19)	0.0378 (11)	0.0459 (12)	−0.0099 (11)	−0.0204 (12)	−0.0058 (9)
C17	0.0566 (12)	0.0302 (9)	0.0409 (10)	−0.0052 (8)	−0.0072 (9)	−0.0066 (8)
C18	0.0673 (14)	0.0495 (12)	0.0479 (12)	0.0003 (10)	−0.0151 (11)	−0.0123 (10)
C19	0.0834 (18)	0.0577 (14)	0.0809 (18)	0.0022 (13)	−0.0319 (15)	−0.0322 (13)
C20	0.157 (3)	0.118 (3)	0.0524 (16)	−0.004 (2)	−0.0293 (19)	−0.0350 (18)

Geometric parameters (Å, º)

Ni1—O1	1.833 (1)	C5—H5	0.9300
Ni1—O1^i	1.833 (1)	C6—H6	0.9300
Ni1—N2^i	1.862 (1)	C8—C9	1.432 (2)
Ni1—N2	1.862 (1)	C8—H8	0.9300
O1—C7	1.322 (2)	C9—C10	1.394 (3)
O2—C4	1.358 (2)	C9—C17	1.453 (3)
O2—H2o	0.85 (1)	C10—C11	1.494 (3)
O3—C18	1.231 (2)	C11—H11a	0.9600
O1W—H1w1	0.84 (1)	C11—H11b	0.9600
O1W—H1w2	0.84 (1)	C11—H11c	0.9600
N1—C7	1.302 (2)	C12—C13	1.393 (3)
N1—N2	1.410 (2)	C12—C17	1.416 (3)
N2—C8	1.299 (2)	C13—C14	1.369 (4)
N3—C10	1.349 (2)	C13—H13	0.9300
N3—C12	1.376 (3)	C14—C15	1.395 (4)
N3—H3n	0.861 (10)	C14—H14	0.9300
N4—C18	1.316 (3)	C15—C16	1.380 (3)
N4—C20	1.443 (3)	C15—H15	0.9300
N4—C19	1.453 (3)	C16—C17	1.390 (3)
C1—C6	1.387 (3)	C16—H16	0.9300
C1—C2	1.394 (3)	C18—H18	0.9300
C1—C7	1.476 (2)	C19—H19a	0.9600
C2—C3	1.381 (3)	C19—H19b	0.9600
C2—H2	0.9300	C19—H19c	0.9600
C3—C4	1.375 (3)	C20—H20a	0.9600
C3—H3	0.9300	C20—H20b	0.9600
C4—C5	1.388 (3)	C20—H20c	0.9600
C5—C6	1.385 (3)
O1—Ni1—N2	83.52 (6)	C10—C9—C17	106.48 (16)
O1—Ni1—N2^i	96.48 (6)	C8—C9—C17	134.51 (17)
O1—Ni1—O1^i	180.0	N3—C10—C9	109.52 (17)
O1^i—Ni1—N2^i	83.52 (6)	N3—C10—C11	119.78 (17)
O1^i—Ni1—N2	96.48 (6)	C9—C10—C11	130.66 (17)
N2^i—Ni1—N2	180.0	C10—C11—H11a	109.5
C7—O1—Ni1	111.37 (10)	C10—C11—H11b	109.5
C4—O2—H2o	114 (2)	H11a—C11—H11b	109.5
H1w1—O1W—H1w2	110 (3)	C10—C11—H11c	109.5
C7—N1—N2	108.06 (14)	H11a—C11—H11c	109.5
C8—N2—N1	119.22 (14)	H11b—C11—H11c	109.5
C8—N2—Ni1	126.36 (12)	N3—C12—C13	129.01 (19)
N1—N2—Ni1	114.32 (11)	N3—C12—C17	108.10 (17)
C10—N3—C12	110.12 (16)	C13—C12—C17	122.9 (2)
C10—N3—H3n	121.7 (16)	C14—C13—C12	117.4 (2)
C12—N3—H3n	128.2 (16)	C14—C13—H13	121.3
C18—N4—C20	122.0 (2)	C12—C13—H13	121.3
C18—N4—C19	121.52 (19)	C13—C14—C15	120.9 (2)
C20—N4—C19	116.5 (2)	C13—C14—H14	119.5
C6—C1—C2	118.08 (17)	C15—C14—H14	119.5
C6—C1—C7	122.32 (17)	C16—C15—C14	121.6 (2)
C2—C1—C7	119.60 (16)	C16—C15—H15	119.2
C3—C2—C1	120.76 (18)	C14—C15—H15	119.2
C3—C2—H2	119.6	C15—C16—C17	119.4 (2)
C1—C2—H2	119.6	C15—C16—H16	120.3
C4—C3—C2	120.65 (19)	C17—C16—H16	120.3
C4—C3—H3	119.7	C16—C17—C12	117.81 (18)
C2—C3—H3	119.7	C16—C17—C9	136.35 (18)
O2—C4—C3	117.86 (19)	C12—C17—C9	105.77 (17)
O2—C4—C5	122.69 (19)	O3—C18—N4	126.3 (2)
C3—C4—C5	119.43 (18)	O3—C18—H18	116.8
C6—C5—C4	119.84 (18)	N4—C18—H18	116.8
C6—C5—H5	120.1	N4—C19—H19a	109.5
C4—C5—H5	120.1	N4—C19—H19b	109.5
C1—C6—C5	121.24 (18)	H19a—C19—H19b	109.5
C1—C6—H6	119.4	N4—C19—H19c	109.5
C5—C6—H6	119.4	H19a—C19—H19c	109.5
N1—C7—O1	122.54 (16)	H19b—C19—H19c	109.5
N1—C7—C1	120.75 (16)	N4—C20—H20a	109.5
O1—C7—C1	116.71 (15)	N4—C20—H20b	109.5
N2—C8—C9	133.60 (17)	H20a—C20—H20b	109.5
N2—C8—H8	113.2	N4—C20—H20c	109.5
C9—C8—H8	113.2	H20a—C20—H20c	109.5
C10—C9—C8	119.01 (16)	H20b—C20—H20c	109.5
N2^i—Ni1—O1—C7	176.52 (12)	Ni1—N2—C8—C9	177.63 (17)
N2—Ni1—O1—C7	−3.48 (12)	N2—C8—C9—C10	−166.0 (2)
C7—N1—N2—C8	172.68 (17)	N2—C8—C9—C17	13.5 (4)
C7—N1—N2—Ni1	−3.80 (19)	C12—N3—C10—C9	0.8 (2)
O1—Ni1—N2—C8	−172.04 (17)	C12—N3—C10—C11	178.84 (19)
O1^i—Ni1—N2—C8	7.96 (17)	C8—C9—C10—N3	178.62 (17)
O1—Ni1—N2—N1	4.15 (12)	C17—C9—C10—N3	−1.1 (2)
O1^i—Ni1—N2—N1	−175.85 (12)	C8—C9—C10—C11	0.8 (3)
N2^i—Ni1—N2—N1	−56 (100)	C17—C9—C10—C11	−178.9 (2)
C6—C1—C2—C3	0.4 (3)	C10—N3—C12—C13	179.3 (2)
C7—C1—C2—C3	−178.95 (19)	C10—N3—C12—C17	−0.1 (2)
C1—C2—C3—C4	−0.2 (3)	N3—C12—C13—C14	−178.0 (3)
C2—C3—C4—O2	−178.8 (2)	C17—C12—C13—C14	1.3 (4)
C2—C3—C4—C5	−0.2 (3)	C12—C13—C14—C15	0.2 (5)
O2—C4—C5—C6	179.0 (2)	C13—C14—C15—C16	−0.5 (6)
C3—C4—C5—C6	0.4 (3)	C14—C15—C16—C17	−0.6 (5)
C2—C1—C6—C5	−0.2 (3)	C15—C16—C17—C12	2.0 (4)
C7—C1—C6—C5	179.16 (19)	C15—C16—C17—C9	178.6 (3)
C4—C5—C6—C1	−0.2 (4)	N3—C12—C17—C16	177.0 (2)
N2—N1—C7—O1	0.9 (2)	C13—C12—C17—C16	−2.4 (3)
N2—N1—C7—C1	−178.49 (15)	N3—C12—C17—C9	−0.5 (2)
Ni1—O1—C7—N1	2.4 (2)	C13—C12—C17—C9	−180.0 (2)
Ni1—O1—C7—C1	−178.19 (13)	C10—C9—C17—C16	−175.9 (3)
C6—C1—C7—N1	5.3 (3)	C8—C9—C17—C16	4.5 (4)
C2—C1—C7—N1	−175.40 (18)	C10—C9—C17—C12	1.0 (2)
C6—C1—C7—O1	−174.15 (18)	C8—C9—C17—C12	−178.7 (2)
C2—C1—C7—O1	5.2 (3)	C20—N4—C18—O3	179.6 (3)
N1—N2—C8—C9	1.6 (3)	C19—N4—C18—O3	−0.2 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2o···O1w^ii	0.85 (1)	1.85 (1)	2.688 (2)	171 (3)
O1w—H1w1···O1	0.84 (1)	2.02 (1)	2.852 (2)	173 (3)
O1w—H1w2···O3	0.84 (1)	1.94 (1)	2.754 (2)	163 (3)
N3—H3n···O3^iii	0.86 (1)	2.00 (1)	2.859 (2)	173 (2)

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