Diethyl [(4-nitrobenzamido)(phen­yl)meth­yl]phospho­nate

Chen, J.-W.; Li, B.-C.; Fang, H.; Wu, Z.; Fang, M.-J.

doi:10.1107/S1600536814007776

organic compounds

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ISSN: 2056-9890

Volume 70| Part 5| May 2014| Page o548

doi:10.1107/S1600536814007776

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Diethyl [(4-nitrobenzamido)(phenyl)methyl]phosphonate

Jing-Wei Chen,^a Bai-Cun Li,^b Hua Fang,^c ^* Zhen Wu ^b and Mei-Juan Fang ^b

^aThe Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen 361005, People's Republic of China, ^bSchool of Pharmaceutical Sciences, Xiamen University, Xiang-An South Road, Xiamen 361100, People's Republic of China, and ^cThe Third Institute of Oceanography of the State Oceanic Administration, Xiamen 361005, People's Republic of China
^*Correspondence e-mail: hfang@tio.org.cn

(Received 24 March 2014; accepted 8 April 2014; online 12 April 2014)

In the title compound, C₁₈H₂₁N₂O₆P, the dihedral angle between the benzene and phenyl rings is 85.1 (2)°. In the crystal, molecules are linked via pairs of N—H⋯O(=P) hydrogen bonds, forming inversion dimers with graph-set notation R₂²(10). One of the ethyl groups is disordered over two sets of sites, with occupancies 0.746 (11) and 0.254 (11).

CCDC reference: 995975

Related literature

For the synthesis, see: Takahashi et al. (1994 ). For a related structure, see: Fang et al. (2004 ). For hydrogen bond graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₈H₂₁N₂O₆P
M_r = 392.34
Triclinic, $[P \overline 1]$
a = 8.112 (3) Å
b = 10.378 (4) Å
c = 12.583 (5) Å
α = 106.321 (7)°
β = 90.188 (8)°
γ = 106.035 (7)°
V = 973.3 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 293 K
0.42 × 0.28 × 0.23 mm

Data collection

Bruker APEX diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.929, T_max = 0.960
4948 measured reflections
3375 independent reflections
2719 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.075
wR(F²) = 0.200
S = 1.09
3375 reflections
259 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.78 (4)	2.15 (4)	2.909 (4)	164 (4)
Symmetry code: (i) -x+1, -y+2, -z+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: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 995975

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814007776/lh5697sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814007776/lh5697Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814007776/lh5697Isup3.cml

checkCIF report

Comment top

The title compound (I) was synthesized for a study of its antimicrobial activity against Bacillus subtilis. This aminophosphonate derivative was found to have weak antimicrobial activity (inhibition zone = 7 mm). The molecular structure of the title compound is shown in Fig. 1. The dihedral angle between the benzene (C2–C7) ring and phenyl (C9–C14) ring is 85.1 (2)°. In the crystal, molecules are linked via pairs of N—H···O(═P) hydrogen bonds forming inversion dimers with with graph-set notation R²₂(10) (Bernstein et al., 1995). One of the ethyl groups (C17/C18) is disordered over two sets of sites with occupancies 0.746 (11) and 0.254 (11). Bond lenths and angles in (I) are in agreement with the values reported for a similar structure (Fang et al., 2004).

Related literature top

For the synthesis, see: Takahashi et al. (1994). For a related structure, see: Fang et al. (2004). For hydrogen bond graph-set notation, see: Bernstein et al. (1995).

Experimental top

The hydrochloride of diethyl amino(phenyl)methylphosphonate was prepared according to the literature procedure (Takahashi et al., 1994). This ester (1.08 g, 5 mmol) was dissolved in dry tetrahydrofuran (20 ml) to which triethylamine (0.7 ml) was added, and the solution was added dropwise to 4-nitrobenzoyl chloride (0.9 g, 5 mmol) in the same solvent (10 ml) (see Fig. 1). After completion of the reaction, the precipitate was separated and the filtrate was extracted with ethyl acetate, dried over anhydrous MgSO₄ and concentrated under vacuum. The residual liquid was purified by column chromatography to give the title compound. Single crystals suitable for X-ray analysis were obtained by slow evaporation of a petroleum ether - ethyl acetate solution (3:1 v/v) of the title compound.

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: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The reaction scheme.
	Fig. 2. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. H atoms are drawn as spheres of arbitrary radii and the open bonds indicate the minor component of disorder.

Diethyl [(4-nitrobenzamido)(phenyl)methyl]phosphonate top

Crystal data top

C₁₈H₂₁N₂O₆P	Z = 2
M_r = 392.34	F(000) = 412
Triclinic, P1	D_x = 1.339 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.112 (3) Å	Cell parameters from 1770 reflections
b = 10.378 (4) Å	θ = 1.3–26.6°
c = 12.583 (5) Å	µ = 0.18 mm⁻¹
α = 106.321 (7)°	T = 293 K
β = 90.188 (8)°	Block, colorless
γ = 106.035 (7)°	0.42 × 0.28 × 0.23 mm
V = 973.3 (6) Å³

Data collection top

Bruker APEX diffractometer	3375 independent reflections
Radiation source: fine-focus sealed tube	2719 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scan	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.929, T_max = 0.960	k = −12→12
4948 measured reflections	l = −8→14

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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.200	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.1021P)² + 0.2844P] where P = (F_o² + 2F_c²)/3
3375 reflections	(Δ/σ)_max = 0.013
259 parameters	Δρ_max = 0.48 e Å⁻³
1 restraint	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₈H₂₁N₂O₆P	γ = 106.035 (7)°
M_r = 392.34	V = 973.3 (6) Å³
Triclinic, P1	Z = 2
a = 8.112 (3) Å	Mo Kα radiation
b = 10.378 (4) Å	µ = 0.18 mm⁻¹
c = 12.583 (5) Å	T = 293 K
α = 106.321 (7)°	0.42 × 0.28 × 0.23 mm
β = 90.188 (8)°

Data collection top

Bruker APEX diffractometer	3375 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2719 reflections with I > 2σ(I)
T_min = 0.929, T_max = 0.960	R_int = 0.028
4948 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	1 restraint
wR(F²) = 0.200	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.48 e Å⁻³
3375 reflections	Δρ_min = −0.23 e Å⁻³
259 parameters

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	Occ. (<1)
P1	0.32681 (11)	0.73988 (8)	0.39408 (7)	0.0472 (3)
O1	0.5803 (4)	0.6502 (2)	0.6389 (2)	0.0749 (8)
O2	0.3346 (3)	0.8870 (2)	0.41776 (19)	0.0576 (6)
O3	0.2957 (3)	0.6646 (2)	0.26662 (18)	0.0591 (7)
O4	0.1843 (3)	0.6511 (3)	0.4480 (2)	0.0675 (7)
O5	0.8608 (8)	1.1843 (7)	1.1263 (4)	0.195 (3)
O6	0.6792 (9)	1.2811 (5)	1.0861 (4)	0.172 (3)
N1	0.5688 (4)	0.8136 (3)	0.5566 (2)	0.0510 (8)
H1N	0.576 (5)	0.893 (4)	0.567 (3)	0.061*
N2	0.7490 (9)	1.1926 (6)	1.0645 (4)	0.124 (2)
C1	0.5887 (4)	0.7714 (3)	0.6449 (3)	0.0504 (8)
C2	0.6243 (4)	0.8826 (3)	0.7554 (3)	0.0513 (8)
C3	0.7279 (5)	0.8703 (5)	0.8364 (3)	0.0724 (11)
H3A	0.7716	0.7938	0.8219	0.087*
C4	0.7674 (6)	0.9689 (6)	0.9376 (4)	0.0849 (13)
H4A	0.8371	0.9599	0.9923	0.102*
C5	0.7041 (6)	1.0796 (5)	0.9574 (3)	0.0797 (14)
C6	0.5969 (6)	1.0951 (4)	0.8798 (3)	0.0790 (13)
H6A	0.5523	1.1712	0.8957	0.095*
C7	0.5574 (5)	0.9937 (4)	0.7773 (3)	0.0633 (10)
H7A	0.4852	1.0014	0.7232	0.076*
C8	0.5261 (4)	0.7180 (3)	0.4444 (2)	0.0469 (8)
H8A	0.5015	0.6220	0.4493	0.056*
C9	0.6651 (4)	0.7392 (3)	0.3678 (3)	0.0470 (8)
C10	0.6906 (5)	0.6247 (4)	0.2896 (3)	0.0609 (9)
H10A	0.6227	0.5351	0.2863	0.073*
C11	0.8151 (6)	0.6411 (5)	0.2164 (4)	0.0807 (13)
H11A	0.8304	0.5630	0.1638	0.097*
C12	0.9163 (6)	0.7726 (5)	0.2213 (4)	0.0899 (14)
H12A	1.0009	0.7845	0.1722	0.108*
C13	0.8918 (6)	0.8858 (5)	0.2989 (4)	0.0892 (14)
H13A	0.9605	0.9752	0.3024	0.107*
C14	0.7690 (5)	0.8704 (4)	0.3711 (3)	0.0676 (10)
H14A	0.7548	0.9492	0.4234	0.081*
C15	0.2262 (6)	0.5160 (4)	0.2178 (3)	0.0771 (12)
H15A	0.1059	0.4863	0.2312	0.092*
H15B	0.2881	0.4670	0.2508	0.092*
C16	0.2434 (10)	0.4827 (5)	0.0984 (4)	0.127 (2)
H16A	0.1971	0.3834	0.0647	0.191*
H16B	0.3628	0.5116	0.0857	0.191*
H16C	0.1814	0.5312	0.0663	0.191*
C17	0.0434 (8)	0.6943 (7)	0.5001 (5)	0.077 (2)	0.746 (11)
H17A	0.0383	0.7802	0.4856	0.092*	0.746 (11)
H17B	−0.0641	0.6225	0.4697	0.092*	0.746 (11)
C18	0.0671 (14)	0.7168 (8)	0.6179 (5)	0.114 (3)	0.746 (11)
H18A	−0.0335	0.7344	0.6517	0.171*	0.746 (11)
H18B	0.1655	0.7961	0.6491	0.171*	0.746 (11)
H18C	0.0851	0.6350	0.6314	0.171*	0.746 (11)
C17A	0.1513 (16)	0.7129 (17)	0.5723 (15)	0.060 (5)*	0.254 (11)
H17C	0.1723	0.6563	0.6175	0.072*	0.254 (11)
H17D	0.2236	0.8086	0.6033	0.072*	0.254 (11)
C18A	−0.0275 (17)	0.707 (2)	0.565 (2)	0.082 (7)*	0.254 (11)
H18D	−0.0526	0.7677	0.6316	0.123*	0.254 (11)
H18E	−0.0973	0.6127	0.5546	0.123*	0.254 (11)
H18F	−0.0521	0.7373	0.5023	0.123*	0.254 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0631 (6)	0.0300 (5)	0.0477 (5)	0.0161 (4)	0.0095 (4)	0.0075 (3)
O1	0.130 (2)	0.0410 (14)	0.0592 (15)	0.0318 (15)	0.0001 (15)	0.0164 (12)
O2	0.0741 (15)	0.0361 (12)	0.0650 (15)	0.0244 (11)	0.0064 (12)	0.0104 (11)
O3	0.0810 (17)	0.0402 (13)	0.0496 (14)	0.0137 (11)	0.0008 (12)	0.0066 (10)
O4	0.0772 (17)	0.0490 (15)	0.0789 (18)	0.0217 (13)	0.0268 (14)	0.0190 (13)
O5	0.184 (5)	0.208 (6)	0.104 (3)	0.025 (4)	−0.043 (4)	−0.058 (4)
O6	0.290 (8)	0.074 (3)	0.094 (3)	0.009 (4)	0.056 (4)	−0.024 (2)
N1	0.085 (2)	0.0280 (13)	0.0423 (15)	0.0223 (14)	0.0062 (13)	0.0075 (12)
N2	0.149 (5)	0.095 (4)	0.063 (3)	−0.031 (3)	0.013 (3)	−0.013 (3)
C1	0.069 (2)	0.0373 (17)	0.0475 (19)	0.0213 (15)	0.0079 (16)	0.0103 (14)
C2	0.063 (2)	0.0424 (18)	0.0457 (18)	0.0104 (16)	0.0098 (16)	0.0135 (15)
C3	0.083 (3)	0.074 (3)	0.057 (2)	0.026 (2)	−0.002 (2)	0.012 (2)
C4	0.089 (3)	0.091 (3)	0.058 (2)	0.012 (3)	−0.007 (2)	0.008 (2)
C5	0.092 (3)	0.067 (3)	0.045 (2)	−0.019 (2)	0.016 (2)	0.0007 (19)
C6	0.119 (4)	0.043 (2)	0.065 (3)	0.015 (2)	0.037 (3)	0.0082 (18)
C7	0.093 (3)	0.048 (2)	0.049 (2)	0.0206 (19)	0.0153 (19)	0.0135 (16)
C8	0.072 (2)	0.0264 (15)	0.0436 (17)	0.0201 (15)	0.0071 (15)	0.0066 (13)
C9	0.0592 (19)	0.0405 (17)	0.0454 (17)	0.0242 (15)	0.0042 (15)	0.0093 (14)
C10	0.073 (2)	0.046 (2)	0.058 (2)	0.0202 (17)	0.0117 (18)	0.0023 (16)
C11	0.097 (3)	0.065 (3)	0.071 (3)	0.031 (2)	0.027 (2)	−0.001 (2)
C12	0.090 (3)	0.087 (3)	0.093 (3)	0.032 (3)	0.045 (3)	0.021 (3)
C13	0.094 (3)	0.060 (3)	0.115 (4)	0.024 (2)	0.045 (3)	0.026 (3)
C14	0.083 (3)	0.0388 (19)	0.082 (3)	0.0241 (18)	0.029 (2)	0.0121 (18)
C15	0.112 (3)	0.041 (2)	0.068 (3)	0.021 (2)	−0.009 (2)	0.0017 (18)
C16	0.230 (7)	0.070 (3)	0.058 (3)	0.031 (4)	−0.006 (4)	−0.007 (2)
C17	0.072 (4)	0.077 (4)	0.093 (5)	0.030 (3)	0.024 (4)	0.033 (3)
C18	0.160 (9)	0.101 (6)	0.080 (5)	0.033 (5)	0.055 (6)	0.028 (4)

Geometric parameters (Å, º) top

P1—O2	1.454 (2)	C9—C10	1.379 (5)
P1—O4	1.553 (3)	C10—C11	1.377 (5)
P1—O3	1.559 (2)	C10—H10A	0.9300
P1—C8	1.829 (3)	C11—C12	1.369 (6)
O1—C1	1.222 (4)	C11—H11A	0.9300
O3—C15	1.435 (4)	C12—C13	1.364 (6)
O4—C17	1.435 (6)	C12—H12A	0.9300
O4—C17A	1.569 (18)	C13—C14	1.358 (6)
O5—N2	1.229 (9)	C13—H13A	0.9300
O6—N2	1.178 (9)	C14—H14A	0.9300
N1—C1	1.328 (4)	C15—C16	1.460 (6)
N1—C8	1.454 (4)	C15—H15A	0.9700
N1—H1N	0.78 (4)	C15—H15B	0.9700
N2—C5	1.482 (6)	C16—H16A	0.9600
C1—C2	1.503 (5)	C16—H16B	0.9600
C2—C7	1.367 (5)	C16—H16C	0.9600
C2—C3	1.374 (5)	C17—C18	1.437 (8)
C3—C4	1.363 (6)	C17—H17A	0.9700
C3—H3A	0.9300	C17—H17B	0.9700
C4—C5	1.345 (7)	C18—H18A	0.9600
C4—H4A	0.9300	C18—H18B	0.9600
C5—C6	1.377 (7)	C18—H18C	0.9600
C6—C7	1.387 (5)	C17A—C18A	1.437 (8)
C6—H6A	0.9300	C17A—H17C	0.9700
C7—H7A	0.9300	C17A—H17D	0.9700
C8—C9	1.497 (5)	C18A—H18D	0.9600
C8—H8A	0.9800	C18A—H18E	0.9600
C9—C14	1.379 (5)	C18A—H18F	0.9600

O2—P1—O4	115.90 (15)	C11—C10—C9	121.0 (4)
O2—P1—O3	111.00 (13)	C11—C10—H10A	119.5
O4—P1—O3	105.86 (14)	C9—C10—H10A	119.5
O2—P1—C8	111.80 (13)	C12—C11—C10	119.8 (4)
O4—P1—C8	103.95 (15)	C12—C11—H11A	120.1
O3—P1—C8	107.74 (14)	C10—C11—H11A	120.1
C15—O3—P1	124.6 (2)	C13—C12—C11	119.2 (4)
C17—O4—P1	125.5 (3)	C13—C12—H12A	120.4
C17—O4—C17A	46.7 (5)	C11—C12—H12A	120.4
P1—O4—C17A	119.6 (6)	C14—C13—C12	121.3 (4)
C1—N1—C8	122.9 (3)	C14—C13—H13A	119.4
C1—N1—H1N	118 (3)	C12—C13—H13A	119.4
C8—N1—H1N	119 (3)	C13—C14—C9	120.7 (4)
O6—N2—O5	124.5 (5)	C13—C14—H14A	119.7
O6—N2—C5	120.8 (7)	C9—C14—H14A	119.7
O5—N2—C5	114.8 (7)	O3—C15—C16	108.7 (4)
O1—C1—N1	123.2 (3)	O3—C15—H15A	110.0
O1—C1—C2	120.7 (3)	C16—C15—H15A	110.0
N1—C1—C2	116.1 (3)	O3—C15—H15B	110.0
C7—C2—C3	119.6 (3)	C16—C15—H15B	110.0
C7—C2—C1	122.4 (3)	H15A—C15—H15B	108.3
C3—C2—C1	118.0 (3)	C15—C16—H16A	109.5
C4—C3—C2	120.8 (4)	C15—C16—H16B	109.5
C4—C3—H3A	119.6	H16A—C16—H16B	109.5
C2—C3—H3A	119.6	C15—C16—H16C	109.5
C5—C4—C3	119.1 (4)	H16A—C16—H16C	109.5
C5—C4—H4A	120.5	H16B—C16—H16C	109.5
C3—C4—H4A	120.5	C18—C17—O4	109.3 (6)
C4—C5—C6	122.3 (4)	C18—C17—H17A	109.8
C4—C5—N2	121.2 (6)	O4—C17—H17A	109.8
C6—C5—N2	116.5 (6)	C18—C17—H17B	109.8
C5—C6—C7	118.0 (4)	O4—C17—H17B	109.8
C5—C6—H6A	121.0	H17A—C17—H17B	108.3
C7—C6—H6A	121.0	C18A—C17A—O4	102.9 (15)
C2—C7—C6	120.2 (4)	C18A—C17A—H17C	111.2
C2—C7—H7A	119.9	O4—C17A—H17C	111.2
C6—C7—H7A	119.9	C18A—C17A—H17D	111.2
N1—C8—C9	114.6 (3)	O4—C17A—H17D	111.2
N1—C8—P1	105.6 (2)	H17C—C17A—H17D	109.1
C9—C8—P1	112.3 (2)	C17A—C18A—H18D	109.5
N1—C8—H8A	108.1	C17A—C18A—H18E	109.5
C9—C8—H8A	108.1	H18D—C18A—H18E	109.5
P1—C8—H8A	108.1	C17A—C18A—H18F	109.5
C14—C9—C10	118.0 (3)	H18D—C18A—H18F	109.5
C14—C9—C8	122.3 (3)	H18E—C18A—H18F	109.5
C10—C9—C8	119.7 (3)

O2—P1—O3—C15	−158.4 (3)	C1—C2—C7—C6	−178.7 (3)
O4—P1—O3—C15	−31.9 (3)	C5—C6—C7—C2	−0.1 (6)
C8—P1—O3—C15	78.9 (3)	C1—N1—C8—C9	−113.4 (3)
O2—P1—O4—C17	12.4 (4)	C1—N1—C8—P1	122.6 (3)
O3—P1—O4—C17	−111.2 (4)	O2—P1—C8—N1	46.0 (2)
C8—P1—O4—C17	135.5 (4)	O4—P1—C8—N1	−79.8 (2)
O2—P1—O4—C17A	−43.3 (6)	O3—P1—C8—N1	168.18 (18)
O3—P1—O4—C17A	−166.8 (6)	O2—P1—C8—C9	−79.5 (2)
C8—P1—O4—C17A	79.8 (6)	O4—P1—C8—C9	154.8 (2)
C8—N1—C1—O1	3.3 (6)	O3—P1—C8—C9	42.7 (2)
C8—N1—C1—C2	−177.2 (3)	N1—C8—C9—C14	−37.0 (4)
O1—C1—C2—C7	−147.5 (4)	P1—C8—C9—C14	83.4 (4)
N1—C1—C2—C7	32.9 (5)	N1—C8—C9—C10	143.8 (3)
O1—C1—C2—C3	32.3 (5)	P1—C8—C9—C10	−95.8 (3)
N1—C1—C2—C3	−147.2 (3)	C14—C9—C10—C11	−0.5 (6)
C7—C2—C3—C4	−1.2 (6)	C8—C9—C10—C11	178.6 (3)
C1—C2—C3—C4	178.9 (4)	C9—C10—C11—C12	0.4 (7)
C2—C3—C4—C5	−0.3 (7)	C10—C11—C12—C13	−0.1 (8)
C3—C4—C5—C6	1.7 (7)	C11—C12—C13—C14	−0.1 (8)
C3—C4—C5—N2	−177.5 (4)	C12—C13—C14—C9	−0.1 (8)
O6—N2—C5—C4	−171.8 (5)	C10—C9—C14—C13	0.4 (6)
O5—N2—C5—C4	7.7 (7)	C8—C9—C14—C13	−178.8 (4)
O6—N2—C5—C6	9.0 (7)	P1—O3—C15—C16	−170.5 (4)
O5—N2—C5—C6	−171.6 (5)	P1—O4—C17—C18	−110.7 (5)
C4—C5—C6—C7	−1.5 (6)	C17A—O4—C17—C18	−11.4 (9)
N2—C5—C6—C7	177.7 (3)	C17—O4—C17A—C18A	10.2 (11)
C3—C2—C7—C6	1.4 (5)	P1—O4—C17A—C18A	122.7 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.78 (4)	2.15 (4)	2.909 (4)	164 (4)

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.78 (4)	2.15 (4)	2.909 (4)	164 (4)

Symmetry code: (i) −x+1, −y+2, −z+1.

Acknowledgements

This work was supported by the National Science Foundation of China (No. 81302652) and the special financial fund of the innovative development of marine economic demonstration project, GD2012-D01–001.

References

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