3-[2-(N,N-Diethyl­amino)­glyoxyloyl]-1H-indol-4-yl acetate monohydrate

In the crystal structure of the title compound, C₁₆H₁₈N₂O₄·H₂O, the substituted indole mol­ecule forms a hydrogen bond to the water mol­ecule. The water mol­ecule in turn interacts with the carbonyl O atom of the acetoxy unit of an adjacent indole mol­ecule and also with the O atom of the acet­amide unit of another indole mol­ecule, giving rise to a hydrogen-bonded helical chain structure that runs along the b axis of the monoclinic unit cell.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.128
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT128_ALERT_4_C Non-standard setting of Space group P21/c   ....    P21/a
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.63 Ratio
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C11    -   C12      =       1.53 Ang.
PLAT702_ALERT_1_C Angle   Calc  116.37(10), Rep  116.50(10), Dev..       1.30 Sigma
              C3   -C8   -C7      1.555   1.555   1.555
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

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

   1 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
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-II (Johnson, 1976); software used to prepare material for publication: SHELXL97.

3-[2-(N,N-Diethylamino)glyoxyloyl]-1H-indol-4-yl acetate monohydrate

Crystal data

C16H18N2O4·H2O	F(000) = 680
Mr = 320.34	Dx = 1.254 Mg m^−3
Monoclinic, P21/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yab	Cell parameters from 931 reflections
a = 12.646 (2) Å	θ = 2.5–26.8°
b = 10.518 (1) Å	µ = 0.09 mm^−1
c = 12.904 (2) Å	T = 293 K
β = 98.703 (2)°	Block, colourless
V = 1696.7 (4) Å^3	0.50 × 0.38 × 0.36 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2880 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.012
Graphite monochromator	θmax = 27.0°, θmin = 2.5°
φ and ω scans	h = −16→16
9454 measured reflections	k = −11→13
3695 independent reflections	l = −10→16

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0694P)^2 + 0.3054P] where P = (Fo^2 + 2Fc^2)/3
3695 reflections	(Δ/σ)max = 0.001
221 parameters	Δρmax = 0.30 e Å^−3
3 restraints	Δρmin = −0.17 e Å^−3

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

	x	y	z	Uiso*/Ueq
O1	0.2665 (1)	0.4409 (1)	0.1367 (1)	0.0527 (3)
O2	0.4382 (1)	0.4820 (2)	0.1248 (1)	0.0725 (4)
O3	0.2848 (1)	0.7145 (1)	0.1412 (1)	0.0566 (3)
O4	0.3046 (1)	0.9470 (1)	0.2926 (1)	0.0594 (3)
O1W	0.4043 (1)	0.5287 (2)	0.6934 (1)	0.0906 (5)
N1	0.3776 (1)	0.5793 (1)	0.4825 (1)	0.0504 (3)
N2	0.4593 (1)	0.9052 (1)	0.2313 (1)	0.0534 (3)
C1	0.3058 (2)	0.5067 (2)	−0.0273 (1)	0.0705 (5)
C2	0.3464 (1)	0.4771 (2)	0.0843 (1)	0.0541 (4)
C3	0.2943 (1)	0.4144 (1)	0.2439 (1)	0.0465 (3)
C4	0.2861 (1)	0.2909 (2)	0.2758 (1)	0.0590 (4)
C5	0.3088 (1)	0.2578 (2)	0.3814 (1)	0.0630 (4)
C6	0.3403 (1)	0.3477 (2)	0.4566 (1)	0.0570 (4)
C7	0.3476 (1)	0.4727 (1)	0.4230 (1)	0.0453 (3)
C8	0.3241 (1)	0.5108 (1)	0.3172 (1)	0.0407 (3)
C9	0.3408 (1)	0.6470 (1)	0.3164 (1)	0.0408 (3)
C10	0.3737 (1)	0.6812 (1)	0.4198 (1)	0.0475 (3)
C11	0.3274 (1)	0.7365 (1)	0.2311 (1)	0.0415 (3)
C12	0.3648 (1)	0.8727 (1)	0.2556 (1)	0.0435 (3)
C13	0.5290 (1)	0.8154 (2)	0.1867 (2)	0.0646 (4)
C14	0.5200 (2)	0.8246 (2)	0.0695 (2)	0.0863 (6)
C15	0.4968 (2)	1.0366 (2)	0.2478 (2)	0.0752 (5)
C16	0.5466 (2)	1.0606 (3)	0.3574 (2)	0.1068 (9)
H1W1	0.454 (1)	0.528 (2)	0.746 (1)	0.096 (7)*
H1W2	0.347 (1)	0.497 (2)	0.708 (2)	0.105 (8)*
H1N	0.395 (2)	0.578 (2)	0.550 (1)	0.069 (5)*
H1A	0.3633	0.5382	−0.0607	0.106*
H1B	0.2507	0.5700	−0.0308	0.106*
H1C	0.2770	0.4309	−0.0623	0.106*
H4	0.2649	0.2282	0.2262	0.071*
H5	0.3025	0.1734	0.4011	0.076*
H6	0.3562	0.3260	0.5271	0.068*
H10	0.3908	0.7636	0.4425	0.057*
H13A	0.5110	0.7295	0.2053	0.078*
H13B	0.6026	0.8312	0.2176	0.078*
H14A	0.5668	0.7635	0.0448	0.129*
H14B	0.5398	0.9086	0.0505	0.129*
H14C	0.4476	0.8077	0.0382	0.129*
H15A	0.4368	1.0940	0.2297	0.090*
H15B	0.5486	1.0546	0.2014	0.090*
H16A	0.5703	1.1473	0.3644	0.160*
H16B	0.6067	1.0048	0.3753	0.160*
H16C	0.4951	1.0451	0.4035	0.160*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0507 (6)	0.0592 (6)	0.0466 (6)	−0.0074 (4)	0.0024 (4)	−0.0101 (4)
O2	0.0499 (6)	0.119 (1)	0.0491 (6)	0.0037 (6)	0.0085 (5)	−0.0023 (6)
O3	0.0649 (6)	0.0573 (6)	0.0443 (6)	−0.0048 (5)	−0.0027 (5)	0.0019 (4)
O4	0.0512 (6)	0.0546 (6)	0.0748 (7)	0.0051 (5)	0.0170 (5)	−0.0119 (5)
O1W	0.0534 (7)	0.166 (2)	0.0506 (7)	−0.0115 (8)	0.0004 (6)	0.0323 (8)
N1	0.0543 (7)	0.0594 (7)	0.0369 (6)	−0.0005 (5)	0.0043 (5)	0.0002 (5)
N2	0.0441 (6)	0.0470 (7)	0.0710 (8)	−0.0022 (5)	0.0143 (6)	−0.0019 (6)
C1	0.077 (1)	0.090 (1)	0.0419 (8)	−0.0017 (9)	0.0026 (7)	−0.0105 (8)
C2	0.0550 (8)	0.0641 (9)	0.0431 (8)	0.0009 (7)	0.0068 (6)	−0.0131 (6)
C3	0.0420 (7)	0.0486 (7)	0.0491 (8)	−0.0022 (5)	0.0076 (6)	−0.0043 (6)
C4	0.0601 (9)	0.0480 (8)	0.070 (1)	−0.0055 (7)	0.0133 (7)	−0.0087 (7)
C5	0.065 (1)	0.0465 (8)	0.080 (1)	−0.0016 (7)	0.0164 (8)	0.0084 (8)
C6	0.0554 (8)	0.0588 (9)	0.0581 (9)	0.0034 (7)	0.0127 (7)	0.0154 (7)
C7	0.0397 (6)	0.0516 (7)	0.0455 (7)	0.0011 (5)	0.0094 (5)	0.0027 (6)
C8	0.0349 (6)	0.0447 (7)	0.0430 (7)	−0.0003 (5)	0.0079 (5)	−0.0003 (5)
C9	0.0368 (6)	0.0445 (7)	0.0412 (7)	−0.0015 (5)	0.0063 (5)	−0.0021 (5)
C10	0.0479 (7)	0.0499 (7)	0.0445 (7)	−0.0026 (6)	0.0060 (6)	−0.0042 (6)
C11	0.0351 (6)	0.0462 (7)	0.0436 (7)	0.0008 (5)	0.0074 (5)	−0.0008 (5)
C12	0.0391 (6)	0.0446 (7)	0.0460 (7)	0.0024 (5)	0.0040 (5)	0.0011 (5)
C13	0.0447 (8)	0.0620 (9)	0.091 (1)	0.0064 (7)	0.0226 (8)	0.0027 (8)
C14	0.090 (1)	0.087 (1)	0.091 (2)	0.008 (1)	0.040 (1)	−0.004 (1)
C15	0.069 (1)	0.061 (1)	0.100 (2)	−0.0215 (8)	0.029 (1)	−0.013 (1)
C16	0.085 (2)	0.136 (2)	0.104 (2)	−0.044 (1)	0.027 (1)	−0.042 (2)

Geometric parameters (Å, º)

O1—C2	1.353 (2)	C15—C16	1.480 (3)
O1—C3	1.402 (2)	O1W—H1W1	0.85 (1)
O2—C2	1.199 (2)	O1W—H1W2	0.85 (1)
O3—C11	1.225 (2)	N1—H1N	0.86 (1)
O4—C12	1.236 (2)	C1—H1A	0.96
N1—C7	1.379 (2)	C1—H1B	0.96
N1—C10	1.339 (2)	C1—H1C	0.96
N2—C12	1.327 (2)	C4—H4	0.93
N2—C15	1.467 (2)	C5—H5	0.93
N2—C13	1.467 (2)	C6—H6	0.93
C1—C2	1.487 (2)	C10—H10	0.93
C3—C4	1.372 (2)	C13—H13A	0.97
C3—C8	1.399 (2)	C13—H13B	0.97
C4—C5	1.393 (2)	C14—H14A	0.96
C5—C6	1.370 (2)	C14—H14B	0.96
C6—C7	1.392 (2)	C14—H14C	0.96
C7—C8	1.410 (2)	C15—H15A	0.97
C8—C9	1.449 (2)	C15—H15B	0.97
C9—C10	1.383 (2)	C16—H16A	0.96
C9—C11	1.439 (2)	C16—H16B	0.96
C11—C12	1.526 (2)	C16—H16C	0.96
C13—C14	1.503 (3)
C2—O1—C3	117.0 (1)	C2—C1—H1B	109.5
C7—N1—C10	109.4 (1)	H1A—C1—H1B	109.5
C12—N2—C13	122.9 (1)	C2—C1—H1C	109.5
C12—N2—C15	119.5 (1)	H1A—C1—H1C	109.5
C13—N2—C15	117.6 (1)	H1B—C1—H1C	109.5
O1—C2—O2	122.8 (1)	C3—C4—H4	119.4
O1—C2—C1	111.6 (1)	C5—C4—H4	119.4
O2—C2—C1	125.6 (2)	C6—C5—H5	119.5
O1—C3—C4	117.7 (1)	C4—C5—H5	119.5
O1—C3—C8	121.7 (1)	C5—C6—H6	121.4
C4—C3—C8	120.5 (1)	C7—C6—H6	121.4
C3—C4—C5	121.1 (2)	N1—C10—H10	124.7
C4—C5—C6	121.0 (2)	C9—C10—H10	124.7
C5—C6—C7	117.2 (1)	N2—C13—H13A	108.9
N1—C7—C6	128.4 (1)	C14—C13—H13A	108.9
N1—C7—C8	108.0 (1)	N2—C13—H13B	108.9
C6—C7—C8	123.7 (1)	C14—C13—H13B	108.9
C3—C8—C7	116.5 (1)	H13A—C13—H13B	107.8
C3—C8—C9	137.4 (1)	C13—C14—H14A	109.5
C7—C8—C9	106.1 (1)	C13—C14—H14B	109.5
C8—C9—C10	105.9 (1)	H14A—C14—H14B	109.5
C10—C9—C11	123.4 (1)	C13—C14—H14C	109.5
C11—C9—C8	130.7 (1)	H14A—C14—H14C	109.5
N1—C10—C9	110.7 (1)	H14B—C14—H14C	109.5
O3—C11—C9	125.8 (1)	N2—C15—H15A	109.1
O3—C11—C12	116.9 (1)	C16—C15—H15A	109.1
C9—C11—C12	117.3 (1)	N2—C15—H15B	109.1
O4—C12—N2	124.0 (1)	C16—C15—H15B	109.1
O4—C12—C11	118.9 (1)	H15A—C15—H15B	107.9
N2—C12—C11	117.0 (1)	C15—C16—H16A	109.5
N2—C13—C14	113.2 (2)	C15—C16—H16B	109.5
N2—C15—C16	112.4 (2)	H16A—C16—H16B	109.5
C10—N1—H1N	127 (1)	C15—C16—H16C	109.5
C7—N1—H1N	124 (1)	H16A—C16—H16C	109.5
H1W1—O1W—H1W2	112 (2)	H16B—C16—H16C	109.5
C2—C1—H1A	109.5
C3—O1—C2—O2	3.0 (2)	C3—C8—C9—C11	2.5 (2)
C3—O1—C2—C1	−177.9 (1)	C7—C8—C9—C11	−178.9 (1)
C2—O1—C3—C4	−112.5 (2)	C7—N1—C10—C9	0.2 (2)
C2—O1—C3—C8	70.9 (2)	C11—C9—C10—N1	179.0 (1)
O1—C3—C4—C5	−177.8 (1)	C8—C9—C10—N1	−0.5 (2)
C8—C3—C4—C5	−1.2 (2)	C10—C9—C11—O3	−169.3 (1)
C3—C4—C5—C6	−0.1 (3)	C8—C9—C11—O3	10.1 (2)
C4—C5—C6—C7	0.5 (2)	C10—C9—C11—C12	7.7 (2)
C10—N1—C7—C6	−179.8 (1)	C8—C9—C11—C12	−173.0 (1)
C10—N1—C7—C8	0.1 (2)	C15—N2—C12—O4	−0.3 (2)
C5—C6—C7—N1	−179.7 (1)	C13—N2—C12—O4	−179.5 (2)
C5—C6—C7—C8	0.3 (2)	C15—N2—C12—C11	176.8 (1)
C4—C3—C8—C7	1.9 (2)	C13—N2—C12—C11	−2.5 (2)
O1—C3—C8—C7	178.5 (1)	O3—C11—C12—O4	94.3 (2)
C4—C3—C8—C9	−179.6 (2)	C9—C11—C12—O4	−82.9 (2)
O1—C3—C8—C9	−3.0 (2)	O3—C11—C12—N2	−82.9 (2)
N1—C7—C8—C3	178.5 (1)	C9—C11—C12—N2	99.9 (2)
C6—C7—C8—C3	−1.5 (2)	C12—N2—C13—C14	98.0 (2)
N1—C7—C8—C9	−0.4 (1)	C15—N2—C13—C14	−81.3 (2)
C6—C7—C8—C9	179.5 (1)	C12—N2—C15—C16	82.8 (2)
C3—C8—C9—C10	−178.1 (2)	C13—N2—C15—C16	−98.0 (2)
C7—C8—C9—C10	0.6 (1)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1W	0.86 (1)	1.91 (1)	2.743 (2)	161 (2)
O1W—H1W1···O2^i	0.85 (1)	1.99 (1)	2.841 (2)	175 (2)
O1W—H1W2···O4^ii	0.85 (1)	1.98 (1)	2.810 (2)	165 (2)

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