Dimethyl [1-(1-allyl-5-iodo-1H-indol-3-yl)-3-hydroxy­prop­yl]phospho­nate

Guo, Y.-C.; Wang, X.-F.; Ding, Y.

doi:10.1107/S1600536807068171

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o384

doi:10.1107/S1600536807068171

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Dimethyl [1-(1-allyl-5-iodo-1H-indol-3-yl)-3-hydroxypropyl]phosphonate

Ying-Cen Guo,^a Xu-Fan Wang ^a and Yu Ding ^a ^*

^aKey Laboratory of Pesticides and Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
^*Correspondence e-mail: dingyu508@gmail.com

(Received 29 November 2007; accepted 21 December 2007; online 9 January 2008)

In the title compound, C₁₆H₂₁INO₄P, the molecular structure is stabilized by a weak intramolecular C—H⋯O hydrogen-bond interaction. The crystal packing is stabilized by strong intermolecular O—H ⋯ O hydogen-bonding interactions 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_r = 449.21
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.102
S = 1.04
3564 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 0.69 e Å⁻³
Δρ_min = −0.30 e Å⁻³
Absolute structure: Flack (1983 ), 1503 Freidel pairs
Flack parameter: 0.00 (1)

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) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

Phosphorus has been recognized as an essential structural constituent of many biomolecules and a crucial element in many biological transformations (Horiguchi & Kandatsu,1959; Allen et al. 1989). With the advances in the development of chiral catalysts, asymmetric synthesis of some phosphorus compounds has been well documented in literatures (Carlone et al., 2007; Yang, et al., 2007; Ibrahem et al., 2007). As part of our ongoing project on enantioselective organocatalysis, a series of α-indolyl phosphonates have been highly enantioselectively synthesized via Friedel-Crafts alkylation of substituted indoles with (E)-dialkyl 3-oxoprop-1-enylphosphonate using MacMillan's imidazolidinone catalysts. The title compound (I) was synthesized and its crystal structure is presented here.

As seen in Fig. 1, the pyrrole plane (C1/C6—C8/N1) and the phenyl ring (C1—C6) are coplanar with each other with a dihedral angle between their mean planes of 2.2 (24)° in the molecule of the title compound (I), and the molecular structure is stablized by a week C12—H12 ··· O1 intramolecular hydrogen bonding interaction (Table 1).

The crystal packing (Fig. 2) is stabilized by strong intermolecular O—H ··· O hydogen bonds interaction (Table 1) to form a zigzag packing arrangement. Dipole–dipole and van der Waals interactions are also effective in the molecular packing in the crystal structure.

Related literature top

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 top

The MacMillan's imidazolidinone catalysts (Fig 3) (0.02 mmol) and TFA (0.02 mmol) were stirred in 1 ml dichloromethane for 5 min at 195 K, then (E)-dialkyl 3-oxoprop-1-enylphosphonate 2 (0.1 mmol) was added and stirred for 15 min. And then 1-allyl-5-iodo-1H-indole 1 (0.11 mmol) was added. After the mixture was stirred for 48 h, the solvent (dichloromethane) was removed under reduced pressure at room temperature, and then the residue was added to a stirring solution of sodium borohydride (18.6 mg, 0.5 mmol, 5 equiv) in methanol (3.0 ml). After 15 min, the reaction was quenched with saturated aqueous NaHCO₃ and extracted with CH₂Cl₂. The combined organic layer was washed with saturated solutions of NaHCO₃ and NaCl and then dried over with Na₂SO₄. The combined organic layer was concentrated in vacuo and the product was purified by flash column chromatography on silica gel (ethyl acetate, R_f = 0.4), (14.3 mg, 48% yield). Compound 5 m: yellow solid; tr (minor) = 53.8 min, tr (major) = 59.5 min (Chiralcel AD—H, λ = 254 nm, 5% i-PrOH / hexanes, flow rate = 1.0 ml/min). ¹H NMR (400 MHz, CDCl₃) δ 2.10–2.18 (m, 1H), 2.28–2.35 (m, 1H), 2.59 (br, 1H), 3.49 (d, J = 10.8 Hz, 3H), 3.73 (d, J = 10.8 Hz, 3H), 3.50–3.75 (m, 3H), 4.67 (d, J = 5.2 Hz, 2H), 5.00 (d, J = 16.8 Hz, 1H), 5.19 (d, J = 10.4 Hz, 1H), 5.90–6.02 (m, 1H), 7.05–7.47 (m, 3H), 7.98 (s, 1H). ¹³C NMR (100 MHz, CDCl₃) δ 29.9, 31.3, 33.3, 48.9, 52.67, 52.75, 53.4, 53.5, 59.7, 59.8, 83.0, 107.9, 111.8, 117.5, 127.9, 128.5, 129.5, 130.2, 132.8, 135.2.; MS (EI) m/z 449 (M⁺), 450 (M⁺+1), 451 (M⁺+2). Elemental Analysis calculated for C₁₆H₂₁INO₄P: C 42.78, H 4.71, N 3.12%. Found: C 42.58, H 4.94, N 3.99%. [α]23D = -22.62 (C=2.35, CHCl₃) (after recrystallization). Single crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a CHCl₃ solution.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Bruker, 2001).

Figures top

	Fig. 1. The molecular structure of (I), showing the atom-labelling scheme and 50% probability displacement ellipsoids.
	Fig. 2. The packing view of the title compound (I) along a axis, showing intermolecular hydrogen bonds as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity..
	Fig. 3. The reaction scheme.

Dimethyl [1-(1-allyl-5-iodo-1H-indol-3-yl)-3-hydroxypropyl]phosphonate top

Crystal data top

C₁₆H₂₁INO₄P	F(000) = 896
M_r = 449.21	D_x = 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 = 2.2–25.6°
b = 10.1295 (6) Å	µ = 1.87 mm⁻¹
c = 22.3722 (12) Å	T = 294 K
V = 1812.57 (17) Å³	Block, colourless
Z = 4	0.20 × 0.10 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3564 independent reflections
Radiation source: fine-focus sealed tube	3314 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
phi and ω scans	θ_max = 26.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −7→9
T_min = 0.706, T_max = 0.835	k = −11→12
10836 measured reflections	l = −27→27

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.102	w = 1/[σ²(F_o²) + (0.0573P)² + 0.6855P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3564 reflections	Δρ_max = 0.69 e Å⁻³
211 parameters	Δρ_min = −0.30 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1503 Freidel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (1)

Crystal data top

C₁₆H₂₁INO₄P	V = 1812.57 (17) Å³
M_r = 449.21	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.9983 (4) Å	µ = 1.87 mm⁻¹
b = 10.1295 (6) Å	T = 294 K
c = 22.3722 (12) Å	0.20 × 0.10 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3564 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	3314 reflections with I > 2σ(I)
T_min = 0.706, T_max = 0.835	R_int = 0.051
10836 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.102	Δρ_max = 0.69 e Å⁻³
S = 1.04	Δρ_min = −0.30 e Å⁻³
3564 reflections	Absolute structure: Flack (1983), 1503 Freidel pairs
211 parameters	Absolute structure parameter: 0.00 (1)
0 restraints

Special details top

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	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₂₁INO₄P
M_r	449.21
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	294
a, b, c (Å)	7.9983 (4), 10.1295 (6), 22.3722 (12)
V (Å³)	1812.57 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.87
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997)
T_min, T_max	0.706, 0.835
No. of measured, independent and observed [I > 2σ(I)] reflections	10836, 3564, 3314
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.102, 1.04
No. of reflections	3564
No. of parameters	211
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.69, −0.30
Absolute structure	Flack (1983), 1503 Freidel pairs
Absolute structure parameter	0.00 (1)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Bruker, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1	0.98	2.47	2.873 (7)	104.0
O1—H1···O4ⁱ	0.82	1.92	2.733 (6)	174.1

Symmetry code: (i) −x, y−1/2, −z+3/2.

Acknowledgements

The authors acknowledge financial support from the Natural Science Foundation of Hubei Province of China (No. 2006ABA175) and the Natural Science Foundation of Central China Normal University, and are indebted to Dr Guangmin Yao of Shijiazhuang Pharmaceutical Group, Zhongqi (sjz) Pharmaceutical Technology Co. Ltd, and Professor Wenjing Xiao and Dr Xianggao Meng of Central China Normal University, for their advice and support.

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