Dimethyl 1-(3-hy­droxy-2-iodo-1-phenyl­prop­yl)-1H-1,2,3-triazole-4,5-dicarboxyl­ate

Fun, H.-K.; Chia, T.S.; Archana, S.; Dinesh, M.; Ponnuswamy, A.

doi:10.1107/S1600536812018193

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1559

doi:10.1107/S1600536812018193

Open

access

Dimethyl 1-(3-hydroxy-2-iodo-1-phenylpropyl)-1H-1,2,3-triazole-4,5-dicarboxylate

Hoong-Kun Fun,^a ^*‡ Tze Shyang Chia,^a Sivasubramanian Archana,^b Murugan Dinesh ^b and Alagusundaram Ponnuswamy ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, Tamil Nadu, India
^*Correspondence e-mail: hkfun@usm.my

(Received 23 April 2012; accepted 23 April 2012; online 28 April 2012)

In the title compound, C₁₅H₁₆IN₃O₅, the central triazole ring is essentially planar (r.m.s deviation = 0.0034 Å) and makes a dihedral angle of 70.14 (5)° with the pendant benzene ring. The mean planes of the two methoxycarbonyl groups make dihedral angles of 22.52 (7) and 40.93 (4)° with the triazole ring. In the crystal, inversion dimers linked by pairs of O—H⋯O hydrogen bonds generate R₂²(18) loops. The dimers are linked by C—H⋯O and C—H⋯N interactions into sheets lying parallel to the ac plane.

Related literature

For background to the industrial applications of 1,2,3-triazoles, see: Wamhoff (1984 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₅H₁₆IN₃O₅
M_r = 445.21
Triclinic, $[P \overline 1]$
a = 8.0504 (3) Å
b = 9.6941 (4) Å
c = 11.1893 (4) Å
α = 106.426 (1)°
β = 91.798 (1)°
γ = 98.606 (1)°
V = 825.65 (5) Å³
Z = 2
Mo Kα radiation
μ = 1.97 mm⁻¹
T = 100 K
0.31 × 0.24 × 0.14 mm

Data collection

Bruker APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.579, T_max = 0.763
21676 measured reflections
5934 independent reflections
5827 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.015
wR(F²) = 0.038
S = 1.10
5934 reflections
223 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.92 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H1O5⋯O3ⁱ	0.74 (2)	2.22 (2)	2.9213 (11)	159 (2)
C9—H9A⋯O1ⁱⁱ	0.97	2.57	3.3595 (13)	139
C13—H13B⋯O3ⁱⁱⁱ	0.96	2.48	3.4375 (14)	174
C13—H13C⋯O5ⁱ	0.96	2.58	3.4247 (14)	147
C15—H15C⋯N2^iv	0.96	2.62	3.4903 (14)	151
Symmetry codes: (i) -x, -y+2, -z; (ii) x-1, y, z; (iii) -x+1, -y+2, -z; (iv) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812018193/hb6752sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812018193/hb6752Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812018193/hb6752Isup3.cml

checkCIF report

Comment top

1,2,3-Triazoles are important in a wide range of industrial applications such as agrochemicals, corrosion inhibitors, dyes, optical brighteners as well as biologically active agents (Wamhoff et al., 1984). As part of our sudies in this area, we now describe the synthesis and structure of the title compound, (I) (Fig. 1).

The central triazole ring (N1–N3/C10/C11) is essentially planar [r.m.s deviation = 0.0034 Å] and makes a dihedral angle of 70.14 (5)° with the terminal benzene ring (C1–C6). The mean planes of the two methyl carboxylate groups (O1/O2/C14/C15 with maximum deviation = 0.0199 (6) Å at atom C14 and O3/O4/C12/C13 with maximum deviation = 0.0060 (6) Å at atom C12) make dihedral angles of 22.52 (7) and 40.93 (4)°, respectively with the triazole ring.

In the crystal (Fig. 2), the molecules are linked by O5—H1O5···O3, C9—H9A···O1, C13—H13B···O3, C13—H13C···O5 and C15—H15C···N2 hydrogen bonds (Table 1) into sheets parallel to ac plane.

Related literature top

For background to the industrial applications of 1,2,3-triazoles, see: Wamhoff (1984). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 3-azido-2-iodo-3-phenylpropan-1-ol (0.3 g, 0.99 mmol) and dimethyl but-2-ynedioate (0.14 g, 0.99 mmol) was heated to reflux in toluene for 3 h. The solvent was evaporated under reduced pressure to afford the crude reaction mass which was then subjected to column chromatography using silica gel (60–120 mesh) as the stationary phase and petroleum ether:ethyl acetate (80:20) as the mobile phase to give colourless blocks of (I) by slow recrystallization from the eluant. Yield: 0.35 g (81%); M.p.: 129–130 °C.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound. The dashed lines represent the hydrogen bonds. For clarity sake, hydrogen atoms not involved in hydrogen bonding have been omitted.

Dimethyl 1-(3-hydroxy-2-iodo-1-phenylpropyl)-1H-1,2,3-triazole-4,5-dicarboxylate top

Crystal data top

C₁₅H₁₆IN₃O₅	Z = 2
M_r = 445.21	F(000) = 440
Triclinic, P1	D_x = 1.791 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0504 (3) Å	Cell parameters from 9309 reflections
b = 9.6941 (4) Å	θ = 2.2–32.6°
c = 11.1893 (4) Å	µ = 1.97 mm⁻¹
α = 106.426 (1)°	T = 100 K
β = 91.798 (1)°	Block, colourless
γ = 98.606 (1)°	0.31 × 0.24 × 0.14 mm
V = 825.65 (5) Å³

Data collection top

Bruker APEX DUO CCD diffractometer	5934 independent reflections
Radiation source: fine-focus sealed tube	5827 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
ϕ and ω scans	θ_max = 32.6°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→11
T_min = 0.579, T_max = 0.763	k = −14→14
21676 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.015	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.038	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0171P)² + 0.3086P] where P = (F_o² + 2F_c²)/3
5934 reflections	(Δ/σ)_max = 0.002
223 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.92 e Å⁻³

Crystal data top

C₁₅H₁₆IN₃O₅	γ = 98.606 (1)°
M_r = 445.21	V = 825.65 (5) Å³
Triclinic, P1	Z = 2
a = 8.0504 (3) Å	Mo Kα radiation
b = 9.6941 (4) Å	µ = 1.97 mm⁻¹
c = 11.1893 (4) Å	T = 100 K
α = 106.426 (1)°	0.31 × 0.24 × 0.14 mm
β = 91.798 (1)°

Data collection top

Bruker APEX DUO CCD diffractometer	5934 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5827 reflections with I > 2σ(I)
T_min = 0.579, T_max = 0.763	R_int = 0.015
21676 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.015	0 restraints
wR(F²) = 0.038	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.49 e Å⁻³
5934 reflections	Δρ_min = −0.92 e Å⁻³
223 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	−0.382668 (7)	0.637377 (7)	0.141512 (5)	0.01603 (2)
O1	0.55901 (10)	1.17479 (8)	0.31744 (7)	0.01765 (13)
O2	0.46348 (10)	1.25049 (8)	0.50897 (7)	0.01713 (13)
O3	0.29674 (10)	1.04776 (7)	0.09582 (6)	0.01498 (12)
O4	0.26687 (9)	0.80305 (7)	0.05704 (6)	0.01300 (12)
O5	−0.09851 (11)	0.94656 (9)	0.12543 (7)	0.01876 (14)
N1	0.13027 (10)	0.84350 (8)	0.29530 (7)	0.01084 (12)
N2	0.13613 (11)	0.87602 (9)	0.42137 (7)	0.01341 (13)
N3	0.25260 (11)	0.99050 (9)	0.46809 (7)	0.01367 (14)
C1	0.11822 (13)	0.50289 (10)	0.15751 (9)	0.01454 (15)
H1A	0.1649	0.5371	0.0942	0.017*
C2	0.15365 (14)	0.37227 (10)	0.17255 (10)	0.01754 (17)
H2A	0.2246	0.3202	0.1202	0.021*
C3	0.08244 (14)	0.31994 (10)	0.26621 (10)	0.01701 (17)
H3A	0.1065	0.2332	0.2771	0.020*
C4	−0.02472 (14)	0.39767 (10)	0.34358 (9)	0.01666 (17)
H4A	−0.0740	0.3616	0.4051	0.020*
C5	−0.05871 (13)	0.52943 (10)	0.32951 (9)	0.01423 (15)
H5A	−0.1295	0.5814	0.3822	0.017*
C6	0.01325 (11)	0.58325 (9)	0.23655 (8)	0.01099 (14)
C7	−0.00868 (11)	0.72960 (9)	0.22038 (8)	0.01059 (13)
H7A	0.0028	0.7236	0.1322	0.013*
C8	−0.17309 (12)	0.78729 (9)	0.25651 (8)	0.01215 (14)
H8A	−0.1878	0.7938	0.3444	0.015*
C9	−0.16977 (13)	0.93812 (10)	0.23842 (9)	0.01566 (16)
H9A	−0.2837	0.9592	0.2369	0.019*
H9B	−0.1044	1.0111	0.3085	0.019*
C10	0.24390 (12)	0.94051 (9)	0.26041 (8)	0.01084 (14)
C11	0.32129 (12)	1.03422 (9)	0.37215 (8)	0.01193 (14)
C12	0.27066 (11)	0.93847 (9)	0.12878 (8)	0.01094 (14)
C13	0.30152 (14)	0.78729 (11)	−0.07305 (8)	0.01628 (16)
H13A	0.2970	0.6859	−0.1166	0.024*
H13B	0.4116	0.8397	−0.0761	0.024*
H13C	0.2187	0.8259	−0.1119	0.024*
C14	0.46100 (12)	1.15881 (10)	0.39366 (8)	0.01275 (14)
C15	0.60447 (14)	1.36969 (11)	0.54233 (10)	0.01921 (18)
H15A	0.5865	1.4391	0.6191	0.029*
H15B	0.6140	1.4164	0.4772	0.029*
H15C	0.7063	1.3326	0.5527	0.029*
H1O5	−0.166 (3)	0.934 (2)	0.0748 (18)	0.032 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.01068 (3)	0.01859 (3)	0.01613 (3)	0.00087 (2)	−0.00104 (2)	0.00174 (2)
O1	0.0165 (3)	0.0192 (3)	0.0152 (3)	−0.0009 (3)	0.0032 (3)	0.0036 (2)
O2	0.0163 (3)	0.0158 (3)	0.0135 (3)	−0.0035 (3)	0.0017 (2)	−0.0018 (2)
O3	0.0186 (3)	0.0131 (3)	0.0134 (3)	0.0007 (2)	0.0005 (2)	0.0052 (2)
O4	0.0170 (3)	0.0114 (3)	0.0099 (3)	0.0024 (2)	0.0029 (2)	0.0018 (2)
O5	0.0203 (4)	0.0221 (3)	0.0174 (3)	0.0057 (3)	0.0010 (3)	0.0101 (3)
N1	0.0121 (3)	0.0110 (3)	0.0088 (3)	0.0010 (2)	0.0003 (2)	0.0024 (2)
N2	0.0157 (4)	0.0143 (3)	0.0089 (3)	0.0004 (3)	0.0004 (3)	0.0024 (2)
N3	0.0148 (4)	0.0140 (3)	0.0108 (3)	0.0000 (3)	0.0007 (3)	0.0024 (2)
C1	0.0162 (4)	0.0122 (3)	0.0152 (4)	0.0034 (3)	0.0042 (3)	0.0033 (3)
C2	0.0192 (4)	0.0130 (4)	0.0205 (4)	0.0052 (3)	0.0041 (3)	0.0033 (3)
C3	0.0191 (4)	0.0117 (3)	0.0202 (4)	0.0019 (3)	−0.0010 (3)	0.0051 (3)
C4	0.0205 (4)	0.0150 (4)	0.0151 (4)	0.0012 (3)	0.0009 (3)	0.0064 (3)
C5	0.0159 (4)	0.0141 (3)	0.0130 (3)	0.0023 (3)	0.0024 (3)	0.0044 (3)
C6	0.0111 (4)	0.0102 (3)	0.0107 (3)	0.0009 (3)	0.0001 (3)	0.0021 (3)
C7	0.0104 (3)	0.0103 (3)	0.0099 (3)	0.0009 (3)	0.0001 (3)	0.0017 (3)
C8	0.0117 (4)	0.0123 (3)	0.0114 (3)	0.0022 (3)	0.0005 (3)	0.0017 (3)
C9	0.0172 (4)	0.0133 (3)	0.0172 (4)	0.0052 (3)	0.0023 (3)	0.0041 (3)
C10	0.0118 (4)	0.0108 (3)	0.0098 (3)	0.0017 (3)	0.0007 (3)	0.0029 (3)
C11	0.0124 (4)	0.0117 (3)	0.0103 (3)	0.0009 (3)	0.0005 (3)	0.0017 (3)
C12	0.0102 (3)	0.0122 (3)	0.0095 (3)	0.0011 (3)	0.0003 (3)	0.0022 (3)
C13	0.0218 (5)	0.0167 (4)	0.0094 (3)	0.0030 (3)	0.0033 (3)	0.0020 (3)
C14	0.0126 (4)	0.0123 (3)	0.0120 (3)	0.0010 (3)	−0.0006 (3)	0.0020 (3)
C15	0.0171 (4)	0.0160 (4)	0.0197 (4)	−0.0040 (3)	−0.0024 (3)	0.0013 (3)

Geometric parameters (Å, º) top

I1—C8	2.1649 (9)	C4—C5	1.3953 (13)
O1—C14	1.2059 (11)	C4—H4A	0.9300
O2—C14	1.3414 (11)	C5—C6	1.3942 (12)
O2—C15	1.4491 (12)	C5—H5A	0.9300
O3—C12	1.2091 (11)	C6—C7	1.5148 (12)
O4—C12	1.3264 (10)	C7—C8	1.5347 (13)
O4—C13	1.4602 (11)	C7—H7A	0.9800
O5—C9	1.4227 (12)	C8—C9	1.5283 (13)
O5—H1O5	0.74 (2)	C8—H8A	0.9800
N1—N2	1.3534 (10)	C9—H9A	0.9700
N1—C10	1.3588 (11)	C9—H9B	0.9700
N1—C7	1.4904 (12)	C10—C11	1.3842 (12)
N2—N3	1.3091 (11)	C10—C12	1.4902 (12)
N3—C11	1.3646 (11)	C11—C14	1.4811 (13)
C1—C2	1.3923 (13)	C13—H13A	0.9600
C1—C6	1.3991 (12)	C13—H13B	0.9600
C1—H1A	0.9300	C13—H13C	0.9600
C2—C3	1.3913 (14)	C15—H15A	0.9600
C2—H2A	0.9300	C15—H15B	0.9600
C3—C4	1.3907 (14)	C15—H15C	0.9600
C3—H3A	0.9300

C14—O2—C15	114.80 (8)	C7—C8—I1	109.17 (6)
C12—O4—C13	115.88 (7)	C9—C8—H8A	109.1
C9—O5—H1O5	110.5 (15)	C7—C8—H8A	109.1
N2—N1—C10	110.40 (7)	I1—C8—H8A	109.1
N2—N1—C7	118.32 (7)	O5—C9—C8	111.51 (7)
C10—N1—C7	130.48 (7)	O5—C9—H9A	109.3
N3—N2—N1	108.01 (7)	C8—C9—H9A	109.3
N2—N3—C11	108.72 (7)	O5—C9—H9B	109.3
C2—C1—C6	120.75 (8)	C8—C9—H9B	109.3
C2—C1—H1A	119.6	H9A—C9—H9B	108.0
C6—C1—H1A	119.6	N1—C10—C11	104.27 (7)
C3—C2—C1	119.75 (9)	N1—C10—C12	124.96 (8)
C3—C2—H2A	120.1	C11—C10—C12	130.77 (8)
C1—C2—H2A	120.1	N3—C11—C10	108.59 (8)
C4—C3—C2	119.87 (9)	N3—C11—C14	122.16 (8)
C4—C3—H3A	120.1	C10—C11—C14	129.19 (8)
C2—C3—H3A	120.1	O3—C12—O4	126.17 (8)
C3—C4—C5	120.40 (9)	O3—C12—C10	123.15 (8)
C3—C4—H4A	119.8	O4—C12—C10	110.64 (7)
C5—C4—H4A	119.8	O4—C13—H13A	109.5
C6—C5—C4	120.08 (9)	O4—C13—H13B	109.5
C6—C5—H5A	120.0	H13A—C13—H13B	109.5
C4—C5—H5A	120.0	O4—C13—H13C	109.5
C5—C6—C1	119.13 (8)	H13A—C13—H13C	109.5
C5—C6—C7	123.26 (8)	H13B—C13—H13C	109.5
C1—C6—C7	117.53 (8)	O1—C14—O2	124.91 (9)
N1—C7—C6	109.14 (7)	O1—C14—C11	124.26 (8)
N1—C7—C8	106.17 (7)	O2—C14—C11	110.83 (8)
C6—C7—C8	118.54 (7)	O2—C15—H15A	109.5
N1—C7—H7A	107.5	O2—C15—H15B	109.5
C6—C7—H7A	107.5	H15A—C15—H15B	109.5
C8—C7—H7A	107.5	O2—C15—H15C	109.5
C9—C8—C7	111.09 (7)	H15A—C15—H15C	109.5
C9—C8—I1	109.34 (6)	H15B—C15—H15C	109.5

C10—N1—N2—N3	−0.86 (10)	I1—C8—C9—O5	−78.79 (9)
C7—N1—N2—N3	−171.70 (8)	N2—N1—C10—C11	0.45 (10)
N1—N2—N3—C11	0.91 (10)	C7—N1—C10—C11	169.83 (9)
C6—C1—C2—C3	0.76 (16)	N2—N1—C10—C12	−179.45 (8)
C1—C2—C3—C4	0.53 (16)	C7—N1—C10—C12	−10.07 (15)
C2—C3—C4—C5	−1.28 (16)	N2—N3—C11—C10	−0.64 (11)
C3—C4—C5—C6	0.75 (15)	N2—N3—C11—C14	−178.05 (8)
C4—C5—C6—C1	0.53 (14)	N1—C10—C11—N3	0.11 (10)
C4—C5—C6—C7	−176.10 (9)	C12—C10—C11—N3	180.00 (9)
C2—C1—C6—C5	−1.29 (15)	N1—C10—C11—C14	177.28 (9)
C2—C1—C6—C7	175.54 (9)	C12—C10—C11—C14	−2.83 (17)
N2—N1—C7—C6	−66.54 (10)	C13—O4—C12—O3	1.45 (14)
C10—N1—C7—C6	124.78 (9)	C13—O4—C12—C10	−176.52 (8)
N2—N1—C7—C8	62.31 (9)	N1—C10—C12—O3	140.62 (10)
C10—N1—C7—C8	−106.37 (10)	C11—C10—C12—O3	−39.26 (16)
C5—C6—C7—N1	90.62 (10)	N1—C10—C12—O4	−41.34 (12)
C1—C6—C7—N1	−86.06 (10)	C11—C10—C12—O4	138.79 (10)
C5—C6—C7—C8	−31.01 (13)	C15—O2—C14—O1	−4.72 (14)
C1—C6—C7—C8	152.31 (8)	C15—O2—C14—C11	175.14 (8)
N1—C7—C8—C9	54.79 (9)	N3—C11—C14—O1	156.03 (10)
C6—C7—C8—C9	177.90 (8)	C10—C11—C14—O1	−20.80 (16)
N1—C7—C8—I1	175.44 (5)	N3—C11—C14—O2	−23.83 (13)
C6—C7—C8—I1	−61.45 (9)	C10—C11—C14—O2	159.34 (9)
C7—C8—C9—O5	41.77 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1O5···O3ⁱ	0.74 (2)	2.22 (2)	2.9213 (11)	159 (2)
C9—H9A···O1ⁱⁱ	0.97	2.57	3.3595 (13)	139
C13—H13B···O3ⁱⁱⁱ	0.96	2.48	3.4375 (14)	174
C13—H13C···O5ⁱ	0.96	2.58	3.4247 (14)	147
C15—H15C···N2^iv	0.96	2.62	3.4903 (14)	151

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₆IN₃O₅
M_r	445.21
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.0504 (3), 9.6941 (4), 11.1893 (4)
α, β, γ (°)	106.426 (1), 91.798 (1), 98.606 (1)
V (Å³)	825.65 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.97
Crystal size (mm)	0.31 × 0.24 × 0.14

Data collection
Diffractometer	Bruker APEX DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.579, 0.763
No. of measured, independent and observed [I > 2σ(I)] reflections	21676, 5934, 5827
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.759

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.015, 0.038, 1.10
No. of reflections	5934
No. of parameters	223
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.92

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1O5···O3ⁱ	0.74 (2)	2.22 (2)	2.9213 (11)	159 (2)
C9—H9A···O1ⁱⁱ	0.97	2.57	3.3595 (13)	139
C13—H13B···O3ⁱⁱⁱ	0.96	2.48	3.4375 (14)	174
C13—H13C···O5ⁱ	0.96	2.58	3.4247 (14)	147
C15—H15C···N2^iv	0.96	2.62	3.4903 (14)	151

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC also thanks the Malaysian Government and USM for the award of a research fellowship.

References

Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wamhoff, H. (1984). Comprehensive Heterocyclic Chemistry, Vol. 5, edited by A. R. Katritzky & C. W. Rees, pp. 669–732. Oxford: Pergamon Press. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1559

doi:10.1107/S1600536812018193

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Di­methyl 1-(3-hy­dr­oxy-2-iodo-1-phenyl­prop­yl)-1H-1,2,3-triazole-4,5-di­carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

Dimethyl 1-(3-hydroxy-2-iodo-1-phenylpropyl)-1H-1,2,3-triazole-4,5-dicarboxylate