N′-(2-Hydr­oxy-3,5-diiodo­benzyl­idene)-2-methoxy­benzohydrazide

Peng, S.-J.; Zhang, F.

doi:10.1107/S160053680901914X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1410

doi:10.1107/S160053680901914X

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N′-(2-Hydroxy-3,5-diiodobenzylidene)-2-methoxybenzohydrazide

San-Jun Peng ^a ^* and Fen Zhang ^b

^aCollege of Chemistry and Biological Engineering, Changsha University of Science and Technology, Changsha 410014, People's Republic of China, and ^bSchool of Foreign Languages, Jiangsu University, Zhenjiang 212013, People's Republic of China
^*Correspondence e-mail: sanjunpeng@163.com

(Received 14 May 2009; accepted 20 May 2009; online 29 May 2009)

The title compound, C₁₅H₁₂I₂N₂O₃, was synthesized by the condensation of equimolar amounts of 3,5-diiodosalicylaldehyde and 2-methoxybenzohydrazide in a methanol solution. There are two independent molecules, A and B, in the asymmetric unit. The dihedral angle between the two benzene rings is 30.2 (2)° for molecule A and 21.7 (2)° for molecule B. There are intramolecular O—H⋯N and N—H⋯O hydrogen bonds in each molecule. The crystal studied was an inversion twin with a 0.59 (3):0.41 (3) domain ratio.

Related literature

For background to Schiff bases and their complexes, see: Ali et al. (2005 ). For related structures, see: Yehye et al. (2008a ,b ); Jing et al. (2006 ); Ling et al. (2008 ).

Experimental

Crystal data

C₁₅H₁₂I₂N₂O₃
M_r = 522.07
Orthorhombic, P n a 2₁
a = 16.073 (2) Å
b = 15.628 (2) Å
c = 13.284 (1) Å
V = 3336.8 (6) Å³
Z = 8
Mo Kα radiation
μ = 3.78 mm⁻¹
T = 298 K
0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.432, T_max = 0.469
26178 measured reflections
7237 independent reflections
4902 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.101
S = 1.00
7237 reflections
407 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.78 e Å⁻³
Δρ_min = −0.56 e Å⁻³
Absolute structure: Flack (1983 ), 3436 Friedel pairs
Flack parameter: 0.59 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯N3	0.82	1.90	2.577 (8)	139
O1—H1⋯N1	0.82	1.92	2.568 (8)	136
N2—H2⋯O3	0.90 (3)	1.91 (6)	2.613 (8)	134 (8)
N4—H4B⋯O6	0.89 (5)	1.98 (7)	2.629 (9)	128 (7)

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680901914X/sj2624sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680901914X/sj2624Isup2.hkl

checkCIF report

Comment top

Schiff bases such as hydrazides are known to act as versatile ligands in coordination chemistry (Ali et al., 2005). We report herein the crystal structure of the new title benzohydrazide derivative (I), Fig. 1.

Compound (I) consists two independent molecules, A and B in the asymmetric unit. The dihedral angles between the two benzene rings are 30.2 (2)° for A and 21.7 (2)° for B, respectively. All the bond lengths are comparable to those observed in other similar compounds (Yehye et al., 2008a,b; Jing et al., 2006); Ling et al., 2008). There are two intramolecular O–H···N and N–H···O hydrogen bonds (Table 1) in each molecule.

Related literature top

For background to Schiff bases and their complexes, see: Ali et al. (2005). For related structures, see: Yehye et al. (2008a,b); Jing et al. (2006); Ling et al. (2008).

Experimental top

2-Methoxybenzohydrazide (0.1 mmol, 16.6 mg) and 3,5-diiodosalicylaldehyde (0.1 mmol, 37.4 mg) were stirred at 318 K in methanol (10 ml) for 30 min. The filtrate was kept in air for a few days depositing colorless block-like crystals of (I).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

Fig. 1. The molecular structure of (I), showing the atom-numbering scheme and 30% probability displacement ellipsoids. H atoms are shown as spheres of arbitrary radii.

N'-(2-Hydroxy-3,5-diiodobenzylidene)-2-methoxybenzohydrazide top

Crystal data top

C₁₅H₁₂I₂N₂O₃	F(000) = 1968
M_r = 522.07	D_x = 2.078 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4242 reflections
a = 16.073 (2) Å	θ = 2.3–24.5°
b = 15.628 (2) Å	µ = 3.78 mm⁻¹
c = 13.284 (1) Å	T = 298 K
V = 3336.8 (6) Å³	Block, colorless
Z = 8	0.23 × 0.20 × 0.20 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	7237 independent reflections
Radiation source: fine-focus sealed tube	4902 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ω scans	θ_max = 27.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −20→20
T_min = 0.432, T_max = 0.469	k = −19→19
26178 measured reflections	l = −16→16

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)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.101	w = 1/[σ²(F_o²) + (0.0412P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
7237 reflections	Δρ_max = 0.78 e Å⁻³
407 parameters	Δρ_min = −0.56 e Å⁻³
3 restraints	Absolute structure: Flack (1983), 3436 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.59 (3)

Crystal data top

C₁₅H₁₂I₂N₂O₃	V = 3336.8 (6) Å³
M_r = 522.07	Z = 8
Orthorhombic, Pna2₁	Mo Kα radiation
a = 16.073 (2) Å	µ = 3.78 mm⁻¹
b = 15.628 (2) Å	T = 298 K
c = 13.284 (1) Å	0.23 × 0.20 × 0.20 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	7237 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	4902 reflections with I > 2σ(I)
T_min = 0.432, T_max = 0.469	R_int = 0.053
26178 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.101	Δρ_max = 0.78 e Å⁻³
S = 1.00	Δρ_min = −0.56 e Å⁻³
7237 reflections	Absolute structure: Flack (1983), 3436 Friedel pairs
407 parameters	Absolute structure parameter: 0.59 (3)
3 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
I3	0.40540 (3)	0.37109 (4)	0.59648 (6)	0.0789 (2)
I4	0.75672 (4)	0.29448 (4)	0.71249 (6)	0.0744 (2)
O4	0.4652 (3)	0.5530 (4)	0.6664 (5)	0.0592 (16)
H4	0.4752	0.5974	0.6971	0.071*
O5	0.4563 (4)	0.7984 (3)	0.7103 (6)	0.0738 (18)
O6	0.7003 (4)	0.8732 (4)	0.7109 (6)	0.0745 (19)
N3	0.5663 (4)	0.6711 (4)	0.7246 (6)	0.0492 (17)
N4	0.5871 (4)	0.7542 (4)	0.7391 (6)	0.0552 (19)
C16	0.6078 (4)	0.5270 (5)	0.7135 (7)	0.0428 (18)
C17	0.5299 (5)	0.4972 (5)	0.6787 (6)	0.0430 (19)
C18	0.5183 (5)	0.4121 (5)	0.6577 (7)	0.052 (2)
C19	0.5820 (5)	0.3546 (5)	0.6660 (6)	0.048 (2)
H19	0.5740	0.2974	0.6493	0.057*
C20	0.6582 (5)	0.3831 (5)	0.6994 (6)	0.047 (2)
C21	0.6718 (5)	0.4676 (5)	0.7198 (7)	0.053 (2)
H21	0.7248	0.4856	0.7381	0.064*
C22	0.6248 (5)	0.6155 (5)	0.7341 (6)	0.047 (2)
H22	0.6777	0.6325	0.7541	0.057*
C23	0.5297 (5)	0.8171 (5)	0.7244 (6)	0.0452 (19)
C24	0.5589 (5)	0.9062 (5)	0.7306 (6)	0.0455 (19)
C25	0.6422 (5)	0.9340 (5)	0.7234 (7)	0.053 (2)
C26	0.6607 (7)	1.0209 (6)	0.7251 (8)	0.074 (3)
H26	0.7154	1.0391	0.7171	0.089*
C27	0.6000 (9)	1.0786 (6)	0.7381 (7)	0.085 (4)
H27	0.6137	1.1362	0.7431	0.102*
C28	0.5176 (8)	1.0543 (7)	0.7445 (7)	0.083 (3)
H28	0.4758	1.0950	0.7518	0.100*
C29	0.4986 (6)	0.9687 (6)	0.7397 (6)	0.061 (2)
H29	0.4430	0.9522	0.7428	0.073*
C30	0.7849 (5)	0.8953 (7)	0.6937 (8)	0.080 (3)
H30A	0.8055	0.9276	0.7499	0.119*
H30B	0.7890	0.9292	0.6336	0.119*
H30C	0.8173	0.8441	0.6860	0.119*
I1	0.81885 (3)	0.63308 (4)	0.55553 (6)	0.0747 (2)
I2	0.46921 (4)	0.71070 (4)	0.43332 (6)	0.0793 (2)
O1	0.7606 (3)	0.4525 (4)	0.4793 (5)	0.0549 (16)
H1	0.7425	0.4041	0.4890	0.082*
O2	0.7669 (3)	0.2033 (4)	0.4301 (7)	0.076 (2)
O3	0.5224 (3)	0.1360 (3)	0.4748 (5)	0.0639 (16)
N1	0.6578 (4)	0.3339 (4)	0.4300 (5)	0.0465 (16)
N2	0.6348 (4)	0.2499 (4)	0.4275 (6)	0.0540 (17)
C1	0.6177 (4)	0.4794 (5)	0.4342 (6)	0.0407 (18)
C2	0.6962 (5)	0.5073 (5)	0.4661 (6)	0.046 (2)
C3	0.7075 (4)	0.5914 (5)	0.4888 (6)	0.048 (2)
C4	0.6443 (5)	0.6517 (5)	0.4757 (6)	0.052 (2)
H4A	0.6537	0.7094	0.4883	0.063*
C5	0.5680 (5)	0.6235 (5)	0.4438 (7)	0.053 (2)
C6	0.5548 (5)	0.5392 (5)	0.4207 (6)	0.0451 (19)
H6	0.5035	0.5219	0.3958	0.054*
C7	0.6016 (5)	0.3892 (5)	0.4185 (7)	0.048 (2)
H7	0.5486	0.3717	0.3996	0.057*
C8	0.6933 (5)	0.1877 (5)	0.4350 (7)	0.0462 (19)
C9	0.6631 (5)	0.0984 (5)	0.4467 (6)	0.044 (2)
C10	0.5797 (5)	0.0735 (5)	0.4667 (6)	0.047 (2)
C11	0.5616 (6)	−0.0131 (6)	0.4790 (7)	0.063 (2)
H11	0.5075	−0.0300	0.4938	0.075*
C12	0.6220 (8)	−0.0729 (6)	0.4696 (8)	0.077 (3)
H12	0.6084	−0.1304	0.4766	0.093*
C13	0.7045 (7)	−0.0501 (6)	0.4495 (7)	0.074 (3)
H13	0.7460	−0.0913	0.4437	0.089*
C14	0.7219 (6)	0.0346 (5)	0.4387 (6)	0.052 (2)
H14	0.7766	0.0503	0.4252	0.062*
C15	0.4365 (5)	0.1115 (6)	0.4888 (7)	0.066 (3)
H15A	0.4293	0.0880	0.5550	0.099*
H15B	0.4215	0.0694	0.4394	0.099*
H15C	0.4015	0.1609	0.4813	0.099*
H2	0.5807 (15)	0.237 (5)	0.435 (7)	0.080*
H4B	0.639 (2)	0.770 (5)	0.754 (7)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I3	0.0459 (3)	0.0612 (4)	0.1295 (6)	−0.0160 (3)	−0.0114 (4)	−0.0033 (4)
I4	0.0618 (4)	0.0584 (4)	0.1029 (5)	0.0198 (3)	−0.0071 (4)	−0.0048 (4)
O4	0.034 (3)	0.054 (3)	0.089 (5)	−0.002 (3)	0.003 (3)	−0.001 (3)
O5	0.056 (4)	0.053 (4)	0.112 (5)	0.002 (3)	0.003 (4)	0.002 (4)
O6	0.048 (4)	0.067 (4)	0.108 (6)	−0.011 (3)	0.003 (4)	0.010 (4)
N3	0.041 (4)	0.044 (4)	0.063 (5)	−0.004 (3)	0.002 (4)	−0.006 (4)
N4	0.045 (4)	0.038 (4)	0.083 (6)	−0.001 (3)	−0.012 (4)	−0.012 (4)
C16	0.029 (4)	0.043 (4)	0.056 (5)	0.008 (3)	−0.007 (4)	0.006 (4)
C17	0.045 (5)	0.042 (4)	0.042 (5)	−0.003 (4)	0.009 (4)	−0.003 (4)
C18	0.038 (4)	0.056 (5)	0.060 (6)	−0.006 (4)	0.001 (4)	0.016 (5)
C19	0.057 (5)	0.040 (4)	0.047 (5)	−0.009 (4)	0.009 (4)	0.008 (4)
C20	0.046 (4)	0.045 (5)	0.051 (5)	0.009 (4)	0.003 (4)	−0.002 (4)
C21	0.039 (4)	0.056 (5)	0.064 (6)	−0.009 (4)	0.013 (4)	−0.005 (5)
C22	0.046 (5)	0.043 (5)	0.053 (6)	−0.009 (4)	−0.005 (4)	−0.009 (4)
C23	0.042 (5)	0.053 (5)	0.041 (5)	−0.006 (4)	0.004 (4)	−0.003 (4)
C24	0.047 (4)	0.050 (5)	0.039 (5)	−0.001 (4)	0.007 (4)	0.006 (4)
C25	0.056 (5)	0.054 (5)	0.048 (5)	−0.002 (4)	−0.005 (4)	0.006 (4)
C26	0.093 (7)	0.053 (6)	0.076 (7)	−0.026 (6)	−0.015 (6)	0.008 (6)
C27	0.152 (12)	0.038 (5)	0.065 (7)	−0.015 (7)	0.019 (7)	0.002 (5)
C28	0.111 (9)	0.064 (7)	0.075 (8)	0.026 (6)	0.023 (7)	0.003 (5)
C29	0.079 (6)	0.056 (6)	0.047 (6)	−0.003 (5)	0.005 (5)	0.003 (4)
C30	0.055 (6)	0.115 (8)	0.069 (7)	−0.009 (6)	0.000 (5)	0.016 (6)
I1	0.0441 (3)	0.0585 (4)	0.1215 (6)	−0.0146 (3)	−0.0043 (3)	−0.0101 (4)
I2	0.0761 (4)	0.0635 (4)	0.0985 (5)	0.0285 (3)	−0.0265 (4)	−0.0121 (4)
O1	0.031 (3)	0.045 (3)	0.088 (5)	0.004 (2)	−0.002 (3)	0.000 (3)
O2	0.033 (3)	0.058 (4)	0.137 (6)	0.003 (3)	0.002 (4)	−0.004 (4)
O3	0.045 (3)	0.051 (3)	0.096 (5)	−0.003 (3)	0.005 (3)	0.000 (3)
N1	0.039 (4)	0.042 (4)	0.058 (4)	0.001 (3)	−0.001 (3)	−0.007 (4)
N2	0.041 (4)	0.039 (4)	0.082 (5)	−0.007 (3)	−0.004 (4)	−0.003 (4)
C1	0.039 (4)	0.037 (4)	0.047 (5)	−0.002 (3)	0.003 (4)	−0.007 (4)
C2	0.035 (4)	0.050 (5)	0.052 (5)	0.002 (4)	0.007 (4)	0.005 (4)
C3	0.038 (4)	0.051 (5)	0.053 (5)	−0.006 (4)	0.001 (4)	−0.005 (4)
C4	0.059 (6)	0.033 (4)	0.065 (6)	0.001 (4)	−0.004 (5)	−0.009 (4)
C5	0.055 (5)	0.048 (5)	0.057 (6)	0.003 (4)	−0.004 (4)	0.008 (5)
C6	0.040 (4)	0.061 (5)	0.035 (5)	0.008 (4)	−0.013 (4)	−0.004 (4)
C7	0.035 (4)	0.056 (5)	0.053 (5)	−0.012 (4)	−0.005 (4)	0.007 (4)
C8	0.043 (5)	0.037 (4)	0.058 (5)	0.002 (4)	0.007 (4)	−0.008 (4)
C9	0.052 (5)	0.045 (4)	0.034 (5)	0.008 (4)	0.005 (4)	0.000 (4)
C10	0.062 (5)	0.043 (5)	0.035 (5)	−0.013 (4)	−0.007 (4)	0.003 (4)
C11	0.070 (6)	0.053 (6)	0.064 (6)	−0.014 (5)	−0.014 (5)	0.001 (5)
C12	0.127 (10)	0.038 (5)	0.068 (7)	−0.007 (6)	−0.009 (6)	−0.002 (5)
C13	0.112 (9)	0.043 (5)	0.068 (7)	0.002 (6)	−0.018 (6)	0.001 (5)
C14	0.061 (5)	0.043 (5)	0.051 (5)	0.004 (4)	−0.001 (5)	−0.008 (4)
C15	0.054 (5)	0.080 (6)	0.065 (6)	−0.029 (5)	−0.002 (5)	−0.002 (5)

Geometric parameters (Å, º) top

I3—C18	2.090 (8)	I1—C3	2.101 (7)
I4—C20	2.111 (7)	I2—C5	2.098 (8)
O4—C17	1.367 (9)	O1—C2	1.355 (8)
O4—H4	0.8200	O1—H1	0.8200
O5—C23	1.229 (9)	O2—C8	1.210 (9)
O6—C25	1.342 (10)	O3—C10	1.348 (10)
O6—C30	1.421 (10)	O3—C15	1.445 (9)
N3—C22	1.287 (10)	N1—C7	1.259 (10)
N3—N4	1.354 (8)	N1—N2	1.364 (8)
N4—C23	1.362 (10)	N2—C8	1.356 (9)
N4—H4B	0.89 (5)	N2—H2	0.90 (3)
C16—C21	1.389 (10)	C1—C6	1.389 (10)
C16—C17	1.414 (10)	C1—C2	1.400 (10)
C16—C22	1.437 (10)	C1—C7	1.448 (10)
C17—C18	1.371 (11)	C2—C3	1.360 (10)
C18—C19	1.366 (11)	C3—C4	1.396 (11)
C19—C20	1.377 (11)	C4—C5	1.370 (11)
C19—H19	0.9300	C4—H4A	0.9300
C20—C21	1.365 (10)	C5—C6	1.369 (10)
C21—H21	0.9300	C6—H6	0.9300
C22—H22	0.9300	C7—H7	0.9300
C23—C24	1.472 (11)	C8—C9	1.485 (11)
C24—C29	1.382 (12)	C9—C14	1.379 (10)
C24—C25	1.412 (11)	C9—C10	1.421 (11)
C25—C26	1.390 (12)	C10—C11	1.393 (11)
C26—C27	1.339 (15)	C11—C12	1.353 (13)
C26—H26	0.9300	C11—H11	0.9300
C27—C28	1.381 (15)	C12—C13	1.399 (14)
C27—H27	0.9300	C12—H12	0.9300
C28—C29	1.374 (12)	C13—C14	1.360 (12)
C28—H28	0.9300	C13—H13	0.9300
C29—H29	0.9300	C14—H14	0.9300
C30—H30A	0.9600	C15—H15A	0.9600
C30—H30B	0.9600	C15—H15B	0.9600
C30—H30C	0.9600	C15—H15C	0.9600

C17—O4—H4	109.4	C2—O1—H1	109.5
C25—O6—C30	120.9 (7)	C10—O3—C15	118.1 (6)
C22—N3—N4	116.9 (7)	C7—N1—N2	117.7 (7)
N3—N4—C23	120.3 (7)	C8—N2—N1	120.1 (6)
N3—N4—H4B	121 (6)	C8—N2—H2	120 (6)
C23—N4—H4B	118 (6)	N1—N2—H2	118 (6)
C21—C16—C17	117.1 (7)	C6—C1—C2	119.0 (7)
C21—C16—C22	119.4 (7)	C6—C1—C7	120.5 (7)
C17—C16—C22	123.3 (7)	C2—C1—C7	120.5 (7)
O4—C17—C18	119.5 (7)	O1—C2—C3	118.7 (7)
O4—C17—C16	120.1 (7)	O1—C2—C1	122.0 (7)
C18—C17—C16	120.4 (7)	C3—C2—C1	119.2 (7)
C19—C18—C17	121.3 (8)	C2—C3—C4	121.8 (7)
C19—C18—I3	118.7 (7)	C2—C3—I1	120.4 (6)
C17—C18—I3	119.6 (6)	C4—C3—I1	117.6 (6)
C18—C19—C20	118.7 (8)	C5—C4—C3	118.2 (8)
C18—C19—H19	120.7	C5—C4—H4A	120.9
C20—C19—H19	120.7	C3—C4—H4A	120.9
C21—C20—C19	121.3 (8)	C6—C5—C4	121.2 (8)
C21—C20—I4	119.9 (6)	C6—C5—I2	119.5 (6)
C19—C20—I4	118.8 (6)	C4—C5—I2	119.3 (6)
C20—C21—C16	121.0 (8)	C5—C6—C1	120.4 (7)
C20—C21—H21	119.5	C5—C6—H6	119.8
C16—C21—H21	119.5	C1—C6—H6	119.8
N3—C22—C16	119.5 (7)	N1—C7—C1	121.5 (8)
N3—C22—H22	120.3	N1—C7—H7	119.2
C16—C22—H22	120.3	C1—C7—H7	119.2
O5—C23—N4	120.1 (7)	O2—C8—N2	121.9 (7)
O5—C23—C24	122.6 (7)	O2—C8—C9	121.0 (7)
N4—C23—C24	117.3 (7)	N2—C8—C9	117.1 (7)
C29—C24—C25	117.0 (8)	C14—C9—C10	117.6 (8)
C29—C24—C23	116.7 (7)	C14—C9—C8	116.6 (7)
C25—C24—C23	126.2 (7)	C10—C9—C8	125.9 (7)
O6—C25—C26	123.0 (8)	O3—C10—C11	123.5 (8)
O6—C25—C24	116.7 (7)	O3—C10—C9	117.4 (7)
C26—C25—C24	120.2 (9)	C11—C10—C9	119.0 (8)
C27—C26—C25	120.3 (10)	C12—C11—C10	120.7 (9)
C27—C26—H26	119.9	C12—C11—H11	119.7
C25—C26—H26	119.9	C10—C11—H11	119.7
C26—C27—C28	121.5 (9)	C11—C12—C13	121.5 (9)
C26—C27—H27	119.3	C11—C12—H12	119.3
C28—C27—H27	119.3	C13—C12—H12	119.3
C29—C28—C27	118.6 (10)	C14—C13—C12	117.5 (10)
C29—C28—H28	120.7	C14—C13—H13	121.2
C27—C28—H28	120.7	C12—C13—H13	121.2
C28—C29—C24	122.4 (9)	C13—C14—C9	123.7 (9)
C28—C29—H29	118.8	C13—C14—H14	118.1
C24—C29—H29	118.8	C9—C14—H14	118.1
O6—C30—H30A	109.5	O3—C15—H15A	109.5
O6—C30—H30B	109.5	O3—C15—H15B	109.5
H30A—C30—H30B	109.5	H15A—C15—H15B	109.5
O6—C30—H30C	109.5	O3—C15—H15C	109.5
H30A—C30—H30C	109.5	H15A—C15—H15C	109.5
H30B—C30—H30C	109.5	H15B—C15—H15C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···N3	0.82	1.90	2.577 (8)	139
O1—H1···N1	0.82	1.92	2.568 (8)	136
N2—H2···O3	0.90 (3)	1.91 (6)	2.613 (8)	134 (8)
N4—H4B···O6	0.89 (5)	1.98 (7)	2.629 (9)	128 (7)

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂I₂N₂O₃
M_r	522.07
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	298
a, b, c (Å)	16.073 (2), 15.628 (2), 13.284 (1)
V (Å³)	3336.8 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.78
Crystal size (mm)	0.23 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.432, 0.469
No. of measured, independent and observed [I > 2σ(I)] reflections	26178, 7237, 4902
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.101, 1.00
No. of reflections	7237
No. of parameters	407
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.78, −0.56
Absolute structure	Flack (1983), 3436 Friedel pairs
Absolute structure parameter	0.59 (3)

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···N3	0.82	1.90	2.577 (8)	139.4
O1—H1···N1	0.82	1.92	2.568 (8)	135.6
N2—H2···O3	0.90 (3)	1.91 (6)	2.613 (8)	134 (8)
N4—H4B···O6	0.89 (5)	1.98 (7)	2.629 (9)	128 (7)

Acknowledgements

We acknowledge Changsha University of Science and Technology for research grants.

References

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