Dimethyl [1-(1-allyl-5-iodo-1H-indol-3-yl)-3-hydroxy-prop-yl]phospho-nate.

In the title compound, C(16)H(21)INO(4)P, the mol-ecular structure is stabilized by a weak intra-molecular C-H⋯O hydrogen-bond inter-action. The crystal packing is stabilized by strong inter-molecular O-H ⋯ O hydogen-bonding inter-actions to form a zigzag packing arrangement.

Related literature

For asymmetric synthesis of phospho­rus compounds, see: Carlone et al. (2007 ▶); Yang, et al. (2007 ▶); Ibrahem et al. (2007 ▶). For related structures, see: Sonar et al. (2006 ▶); Chen et al. (2007 ▶); Butcher et al. (2007 ▶). For related literature, see: Allen et al. (1989 ▶); Horiguchi & Kandatsu (1959 ▶).

Experimental

Crystal data

C16H21INO4P

M = 449.21

Orthorhombic,

a = 7.9983 (4) Å

b = 10.1295 (6) Å

c = 22.3722 (12) Å

V = 1812.57 (17) Å3

Z = 4

Mo Kα radiation

μ = 1.87 mm−1

T = 294 (2) K

0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.706, T max = 0.835

10836 measured reflections

3564 independent reflections

3314 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.102

S = 1.04

3564 reflections

211 parameters

H-atom parameters constrained

Δρmax = 0.69 e Å−3

Δρmin = −0.30 e Å−3

Absolute structure: Flack (1983 ▶), 1503 Freidel pairs

Flack parameter: 0.00 (1)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Bruker, 2001 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068171/at2520sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068171/at2520Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H21INO4P	F000 = 896
Mr = 449.21	Dx = 1.646 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5073 reflections
a = 7.9983 (4) Å	θ = 2.2–25.6º
b = 10.1295 (6) Å	µ = 1.87 mm−1
c = 22.3722 (12) Å	T = 294 (2) K
V = 1812.57 (17) Å3	Block, colourless
Z = 4	0.20 × 0.10 × 0.10 mm

Bruker SMART CCD area-detector diffractometer	3314 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.051
T = 294(2) K	θmax = 26.0º
phi and ω scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 1997)	h = −7→9
Tmin = 0.706, Tmax = 0.835	k = −11→12
10836 measured reflections	l = −27→27
3564 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.042	w = 1/[σ2(Fo2) + (0.0573P)2 + 0.6855P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.102	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.69 e Å−3
3564 reflections	Δρmin = −0.30 e Å−3
211 parameters	Extinction correction: none
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1503 Freidel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.00 (1)

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.

	x	y	z	Uiso*/Ueq
I1	−0.17244 (5)	−0.23507 (4)	1.053601 (16)	0.06002 (15)
C1	−0.1488 (6)	0.1982 (4)	0.96323 (18)	0.0340 (9)
C2	−0.2151 (6)	0.1860 (5)	1.0201 (2)	0.0408 (11)
H2	−0.2575	0.2587	1.0404	0.049*
C3	−0.2158 (7)	0.0611 (6)	1.0455 (2)	0.0460 (12)
H3	−0.2580	0.0495	1.0838	0.055*
C4	−0.1542 (7)	−0.0467 (5)	1.0142 (2)	0.0414 (11)
C5	−0.0842 (6)	−0.0348 (5)	0.95801 (19)	0.0364 (10)
H5	−0.0414	−0.1081	0.9382	0.044*
C6	−0.0794 (5)	0.0896 (4)	0.93175 (17)	0.0299 (9)
C7	−0.0233 (5)	0.1394 (4)	0.87529 (18)	0.0303 (9)
C8	−0.0615 (5)	0.2707 (5)	0.87450 (19)	0.0365 (10)
H8	−0.0395	0.3272	0.8427	0.044*
C9	−0.1972 (10)	0.4394 (5)	0.9422 (2)	0.0627 (17)
H9A	−0.2818	0.4309	0.9731	0.075*
H9B	−0.1050	0.4893	0.9591	0.075*
C10	−0.2659 (14)	0.5131 (9)	0.8942 (4)	0.105 (3)
H10	−0.3574	0.4747	0.8753	0.126*
C11	−0.2201 (13)	0.6240 (7)	0.8734 (3)	0.089 (3)
H11A	−0.1294	0.6679	0.8902	0.107*
H11B	−0.2772	0.6613	0.8414	0.107*
C12	0.0602 (6)	0.0611 (5)	0.82594 (19)	0.0324 (9)
H12	0.0481	−0.0329	0.8355	0.039*
C13	−0.0169 (6)	0.0843 (5)	0.76336 (19)	0.0414 (11)
H13A	−0.0210	0.1785	0.7555	0.050*
H13B	0.0547	0.0443	0.7334	0.050*
C14	−0.1891 (8)	0.0284 (6)	0.7576 (2)	0.0541 (14)
H14A	−0.2652	0.0777	0.7829	0.065*
H14B	−0.2268	0.0374	0.7166	0.065*
C15	0.5194 (7)	0.0595 (7)	0.9005 (3)	0.0577 (15)
H15A	0.5880	0.0042	0.8757	0.087*
H15B	0.5363	0.0367	0.9417	0.087*
H15C	0.5494	0.1503	0.8943	0.087*
C16	0.3565 (9)	−0.1289 (6)	0.7724 (3)	0.0686 (18)
H16A	0.4059	−0.1626	0.8084	0.103*
H16B	0.4166	−0.1620	0.7384	0.103*
H16C	0.2419	−0.1566	0.7701	0.103*
N1	−0.1369 (5)	0.3078 (4)	0.92702 (16)	0.0379 (9)
O1	−0.1922 (9)	−0.1050 (5)	0.7740 (3)	0.112 (2)
H1	−0.2269	−0.1492	0.7459	0.168*
O2	0.3445 (4)	0.0404 (3)	0.88494 (12)	0.0386 (7)
O3	0.3641 (4)	0.0129 (4)	0.77276 (15)	0.0494 (9)
O4	0.3217 (5)	0.2376 (3)	0.81376 (16)	0.0521 (8)
P1	0.28050 (14)	0.09837 (13)	0.82350 (5)	0.0338 (3)

	U11	U22	U33	U12	U13	U23
I1	0.0725 (3)	0.0485 (2)	0.0591 (2)	−0.00777 (18)	0.00460 (18)	0.01635 (16)
C1	0.032 (2)	0.034 (2)	0.036 (2)	0.0011 (18)	−0.0051 (17)	−0.0074 (16)
C2	0.037 (2)	0.050 (3)	0.036 (2)	0.006 (2)	0.0039 (19)	−0.006 (2)
C3	0.047 (3)	0.058 (3)	0.032 (2)	0.000 (2)	0.008 (2)	0.001 (2)
C4	0.041 (3)	0.045 (3)	0.038 (2)	−0.003 (2)	−0.003 (2)	0.0070 (19)
C5	0.032 (2)	0.037 (2)	0.040 (3)	−0.0025 (19)	0.0006 (19)	−0.0012 (19)
C6	0.024 (2)	0.038 (2)	0.028 (2)	0.0039 (18)	−0.0029 (16)	−0.0024 (17)
C7	0.023 (2)	0.038 (2)	0.030 (2)	0.0002 (18)	−0.0002 (16)	−0.0048 (17)
C8	0.037 (2)	0.038 (2)	0.035 (2)	−0.003 (2)	0.0003 (18)	−0.0033 (19)
C9	0.104 (5)	0.039 (3)	0.045 (3)	0.022 (3)	0.005 (4)	−0.002 (2)
C10	0.141 (8)	0.083 (6)	0.090 (6)	0.057 (6)	0.025 (5)	0.008 (5)
C11	0.157 (8)	0.053 (4)	0.058 (4)	0.043 (5)	0.035 (4)	0.010 (3)
C12	0.034 (2)	0.032 (2)	0.031 (2)	0.0014 (19)	0.0026 (18)	−0.0003 (18)
C13	0.042 (3)	0.054 (3)	0.028 (2)	0.002 (2)	−0.0016 (19)	−0.007 (2)
C14	0.056 (3)	0.051 (3)	0.055 (3)	0.000 (3)	−0.026 (3)	−0.006 (2)
C15	0.038 (3)	0.080 (4)	0.056 (3)	−0.006 (3)	−0.013 (2)	0.014 (3)
C16	0.060 (4)	0.062 (4)	0.083 (4)	0.011 (3)	0.004 (3)	−0.029 (3)
N1	0.042 (2)	0.035 (2)	0.0367 (19)	0.0083 (17)	0.0030 (16)	−0.0041 (15)
O1	0.153 (6)	0.054 (3)	0.129 (5)	−0.034 (4)	−0.088 (4)	0.005 (3)
O2	0.0300 (16)	0.0523 (19)	0.0334 (15)	−0.0042 (16)	−0.0025 (14)	0.0044 (13)
O3	0.035 (2)	0.071 (3)	0.0416 (18)	0.0069 (17)	0.0066 (15)	−0.0039 (17)
O4	0.0469 (19)	0.047 (2)	0.062 (2)	−0.007 (2)	−0.0022 (16)	0.0139 (16)
P1	0.0292 (6)	0.0419 (7)	0.0304 (5)	0.0007 (5)	0.0017 (4)	0.0023 (5)

I1—C4	2.107 (5)	C11—H11B	0.9300
C1—N1	1.378 (6)	C12—C13	1.548 (6)
C1—C2	1.383 (6)	C12—P1	1.803 (4)
C1—C6	1.419 (6)	C12—H12	0.9800
C2—C3	1.387 (7)	C13—C14	1.495 (8)
C2—H2	0.9300	C13—H13A	0.9700
C3—C4	1.387 (7)	C13—H13B	0.9700
C3—H3	0.9300	C14—O1	1.400 (7)
C4—C5	1.382 (6)	C14—H14A	0.9700
C5—C6	1.391 (7)	C14—H14B	0.9700
C5—H5	0.9300	C15—O2	1.455 (6)
C6—C7	1.432 (6)	C15—H15A	0.9600
C7—C8	1.365 (7)	C15—H15B	0.9600
C7—C12	1.514 (6)	C15—H15C	0.9600
C8—N1	1.374 (5)	C16—O3	1.438 (7)
C8—H8	0.9300	C16—H16A	0.9600
C9—C10	1.419 (10)	C16—H16B	0.9600
C9—N1	1.458 (6)	C16—H16C	0.9600
C9—H9A	0.9700	O1—H1	0.8200
C9—H9B	0.9700	O2—P1	1.580 (3)
C10—C11	1.270 (12)	O3—P1	1.576 (4)
C10—H10	0.9300	O4—P1	1.464 (4)
C11—H11A	0.9300
N1—C1—C2	129.7 (4)	C7—C12—H12	107.8
N1—C1—C6	107.8 (4)	C13—C12—H12	107.8
C2—C1—C6	122.5 (4)	P1—C12—H12	107.8
C1—C2—C3	117.3 (4)	C14—C13—C12	112.8 (4)
C1—C2—H2	121.3	C14—C13—H13A	109.0
C3—C2—H2	121.3	C12—C13—H13A	109.0
C4—C3—C2	120.7 (4)	C14—C13—H13B	109.0
C4—C3—H3	119.7	C12—C13—H13B	109.0
C2—C3—H3	119.7	H13A—C13—H13B	107.8
C5—C4—C3	122.2 (4)	O1—C14—C13	111.1 (5)
C5—C4—I1	119.2 (4)	O1—C14—H14A	109.4
C3—C4—I1	118.5 (3)	C13—C14—H14A	109.4
C4—C5—C6	118.4 (4)	O1—C14—H14B	109.4
C4—C5—H5	120.8	C13—C14—H14B	109.4
C6—C5—H5	120.8	H14A—C14—H14B	108.0
C5—C6—C1	118.8 (4)	O2—C15—H15A	109.5
C5—C6—C7	134.4 (4)	O2—C15—H15B	109.5
C1—C6—C7	106.7 (4)	H15A—C15—H15B	109.5
C8—C7—C6	106.5 (4)	O2—C15—H15C	109.5
C8—C7—C12	126.8 (4)	H15A—C15—H15C	109.5
C6—C7—C12	126.7 (4)	H15B—C15—H15C	109.5
C7—C8—N1	110.8 (4)	O3—C16—H16A	109.5
C7—C8—H8	124.6	O3—C16—H16B	109.5
N1—C8—H8	124.6	H16A—C16—H16B	109.5
C10—C9—N1	115.6 (5)	O3—C16—H16C	109.5
C10—C9—H9A	108.4	H16A—C16—H16C	109.5
N1—C9—H9A	108.4	H16B—C16—H16C	109.5
C10—C9—H9B	108.4	C8—N1—C1	108.2 (4)
N1—C9—H9B	108.4	C8—N1—C9	126.6 (4)
H9A—C9—H9B	107.4	C1—N1—C9	125.2 (4)
C11—C10—C9	129.1 (11)	C14—O1—H1	109.5
C11—C10—H10	115.5	C15—O2—P1	118.1 (3)
C9—C10—H10	115.5	C16—O3—P1	122.4 (4)
C10—C11—H11A	120.0	O4—P1—O3	109.0 (2)
C10—C11—H11B	120.0	O4—P1—O2	114.5 (2)
H11A—C11—H11B	120.0	O3—P1—O2	106.55 (19)
C7—C12—C13	113.8 (4)	O4—P1—C12	115.2 (2)
C7—C12—P1	110.1 (3)	O3—P1—C12	108.7 (2)
C13—C12—P1	109.3 (3)	O2—P1—C12	102.26 (19)
N1—C1—C2—C3	177.8 (5)	C7—C12—C13—C14	−69.1 (6)
C6—C1—C2—C3	−1.6 (7)	P1—C12—C13—C14	167.4 (4)
C1—C2—C3—C4	−0.9 (7)	C12—C13—C14—O1	−53.2 (7)
C2—C3—C4—C5	2.5 (8)	C7—C8—N1—C1	−0.1 (5)
C2—C3—C4—I1	−176.4 (4)	C7—C8—N1—C9	−179.2 (5)
C3—C4—C5—C6	−1.5 (7)	C2—C1—N1—C8	−179.9 (5)
I1—C4—C5—C6	177.4 (3)	C6—C1—N1—C8	−0.5 (5)
C4—C5—C6—C1	−1.0 (6)	C2—C1—N1—C9	−0.8 (8)
C4—C5—C6—C7	−177.9 (5)	C6—C1—N1—C9	178.7 (5)
N1—C1—C6—C5	−176.9 (4)	C10—C9—N1—C8	35.3 (10)
C2—C1—C6—C5	2.6 (6)	C10—C9—N1—C1	−143.6 (7)
N1—C1—C6—C7	0.8 (5)	C16—O3—P1—O4	175.5 (4)
C2—C1—C6—C7	−179.7 (4)	C16—O3—P1—O2	51.4 (5)
C5—C6—C7—C8	176.3 (5)	C16—O3—P1—C12	−58.1 (5)
C1—C6—C7—C8	−0.8 (5)	C15—O2—P1—O4	−51.1 (5)
C5—C6—C7—C12	−3.0 (8)	C15—O2—P1—O3	69.5 (4)
C1—C6—C7—C12	179.9 (4)	C15—O2—P1—C12	−176.4 (4)
C6—C7—C8—N1	0.6 (5)	C7—C12—P1—O4	−58.6 (4)
C12—C7—C8—N1	179.9 (4)	C13—C12—P1—O4	67.1 (4)
N1—C9—C10—C11	−120.5 (9)	C7—C12—P1—O3	178.7 (3)
C8—C7—C12—C13	−47.8 (6)	C13—C12—P1—O3	−55.6 (4)
C6—C7—C12—C13	131.4 (5)	C7—C12—P1—O2	66.3 (3)
C8—C7—C12—P1	75.3 (5)	C13—C12—P1—O2	−168.0 (3)
C6—C7—C12—P1	−105.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1	0.98	2.47	2.873 (7)	104
O1—H1···O4i	0.82	1.92	2.733 (6)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1	0.98	2.47	2.873 (7)	104
O1—H1⋯O4i	0.82	1.92	2.733 (6)	174

Symmetry code: (i) .