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ISSN: 2056-9890

Diiso­propyl [(4-meth­­oxy­benzamido)(p-tol­yl)meth­yl]phospho­nate

aThe Third Institute of Oceanography of the State Oceanic Administration, Xiamen 361005, People's Republic of China
*Correspondence e-mail: hfang@tio.org.cn

(Received 11 February 2014; accepted 26 February 2014; online 12 March 2014)

The asymmetric unit of the title compound, C22H30NO5P, contains two independent mol­ecules in which the dihedral angles between the benzene rings are 82.0 (2) and 78.4 (2)°. In the crystal, each mol­ecule forms an inversion dimer via a pair of N—H⋯O(=P) hydrogen bonds.

Related literature

For a related structure, see: Giarda et al. (1973[Giarda, L., Garbassi, F. & Calcaterra, M. (1973). Acta Cryst. B29, 1826-1829.]).

[Scheme 1]

Experimental

Crystal data
  • C22H30NO5P

  • Mr = 419.44

  • Triclinic, [P \overline 1]

  • a = 12.4900 (7) Å

  • b = 14.0338 (8) Å

  • c = 14.5693 (9) Å

  • α = 73.389 (5)°

  • β = 76.324 (5)°

  • γ = 78.609 (5)°

  • V = 2354.5 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.15 mm−1

  • T = 293 K

  • 0.44 × 0.32 × 0.18 mm

Data collection
  • Bruker APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SAINT, SMART and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.938, Tmax = 0.974

  • 17787 measured reflections

  • 7970 independent reflections

  • 4850 reflections with I > 2σ(I)

  • Rint = 0.048

Refinement
  • R[F2 > 2σ(F2)] = 0.067

  • wR(F2) = 0.237

  • S = 1.08

  • 7970 reflections

  • 523 parameters

  • H-atom parameters constrained

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1A⋯O2i 0.86 2.20 3.021 (4) 159
N2—H2A⋯O7ii 0.86 2.20 3.013 (4) 157
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x, -y, -z+1.

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT, SMART and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT, SMART and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The title compound, (I), was synthesized for a study of its antimicrobial activity against Bacillus subtilis. The hydroxyphosphonic acid derivative was found to have moderate antimicrobial activity (inhibition zone = 10 mm). The adjacent bonds P1—O3 and P1—O4 [mean 1.557 (8) Å] are similar to that in ammonium dimethylphosphate [1.559 (7) Å; Giarda et al., 1973]. The reaction scheme for (I) is shown in Fig. 1.

The title compound (I) contains two independent molecules which are shown in Figs. 2 and 3. The dihedral angle between the benzene rings in each are 82.0 (2) ° [C2-C7/C9-C14] and 78.4 (2) ° [C23-C28/C30-C35]. In the crystal, each molecule forms an inversion dimer via a pair of N—H···O(P) hydrogen bonds (Fig. 4).

Related literature top

For a related structure, see: Giarda et al. (1973).

Experimental top

Triphenylphosphine (0.39 g, 1.5 mmol) and hexachloroethane (0.39 g, 1.2 mmol) in dried 1,2-dichloroethane (15 ml) were reacted for 1 h in an ice bath. The resulting solution was added dropwise to a mixture of the hydrochloride of dialkyl α-aminotolylphosphonate (0.28 g, 1.0 mmol) and 4-methoxybenzoic acid (0.15 g, 1.0 mmol) in 1,2-dichloroethane (10 ml) and triethylamine (0.4 ml). After completion of the reaction, the solvent was removed to give the crude product, which was purified by recrystallization from hot ethanol. Single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of a petroleum ether C ethyl/acetate solution (1:1 v/v) of the title compound. Analysis calculated for C22H30NO5P: C 63.00, H 7.21, N 3.34; Found C 63.38, H 7.16, N 3.39.

Refinement top

The H atoms were positioned geometrically (C—H = 0.93, 0.98 or 0.96 A for benzene, tertiary or methyl H atoms, respectively, and N—H = 0.86 Å) and were included in the refinement in the riding-model approximation. The displacement parameters of the methyl H atoms were set at 1.5 Ueq of their parent atoms, while those of the other H atoms were set at 1.2 Ueq(C,N).

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: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The reaction scheme for the formation of the title compound.
[Figure 2] Fig. 2. The molecular structure of one independent molecule. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as spheres of arbitrary radii.
[Figure 3] Fig. 3. The molecular structure of the other independent molecule. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as spheres of arbitrary radii.
[Figure 4] Fig. 4. Part of the crystal structure with hydrogen bonds shown as dashed lines.
Diisopropyl [(4-methoxybenzamido)(p-tolyl)methyl]phosphonate top
Crystal data top
C22H30NO5PZ = 4
Mr = 419.44F(000) = 896
Triclinic, P1Dx = 1.183 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.4900 (7) ÅCell parameters from 1986 reflections
b = 14.0338 (8) Åθ = 1.3–27.1°
c = 14.5693 (9) ŵ = 0.15 mm1
α = 73.389 (5)°T = 293 K
β = 76.324 (5)°Block, colorless
γ = 78.609 (5)°0.44 × 0.32 × 0.18 mm
V = 2354.5 (2) Å3
Data collection top
Bruker APEX CCD
diffractometer
7970 independent reflections
Radiation source: fine-focus sealed tube4850 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
ϕ and ω scansθmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1414
Tmin = 0.938, Tmax = 0.974k = 1616
17787 measured reflectionsl = 1617
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.237H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.1456P)2]
where P = (Fo2 + 2Fc2)/3
7970 reflections(Δ/σ)max < 0.001
523 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C22H30NO5Pγ = 78.609 (5)°
Mr = 419.44V = 2354.5 (2) Å3
Triclinic, P1Z = 4
a = 12.4900 (7) ÅMo Kα radiation
b = 14.0338 (8) ŵ = 0.15 mm1
c = 14.5693 (9) ÅT = 293 K
α = 73.389 (5)°0.44 × 0.32 × 0.18 mm
β = 76.324 (5)°
Data collection top
Bruker APEX CCD
diffractometer
7970 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
4850 reflections with I > 2σ(I)
Tmin = 0.938, Tmax = 0.974Rint = 0.048
17787 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0670 restraints
wR(F2) = 0.237H-atom parameters constrained
S = 1.08Δρmax = 0.37 e Å3
7970 reflectionsΔρmin = 0.24 e Å3
523 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
xyzUiso*/Ueq
P10.57811 (7)0.44284 (7)0.16751 (6)0.0520 (3)
N10.6169 (2)0.6091 (2)0.0288 (2)0.0516 (7)
H1A0.56850.60270.00150.062*
C10.6337 (3)0.7016 (3)0.0261 (3)0.0638 (10)
O10.7087 (3)0.7155 (2)0.0598 (3)0.1190 (14)
O20.49931 (17)0.41867 (18)0.11966 (17)0.0571 (6)
C20.5546 (3)0.7864 (2)0.0178 (3)0.0582 (9)
P20.14534 (7)0.06980 (7)0.34174 (7)0.0566 (3)
N20.1934 (2)0.0972 (2)0.4752 (2)0.0547 (7)
H2A0.12390.09690.50070.066*
O30.52694 (19)0.5103 (2)0.2420 (2)0.0708 (7)
C30.5913 (4)0.8747 (3)0.0739 (4)0.0982 (16)
H3A0.66680.87990.08720.118*
O40.6468 (2)0.35073 (19)0.22714 (18)0.0659 (7)
C40.5166 (6)0.9569 (4)0.1114 (5)0.1155 (19)
H4A0.54321.01560.15050.139*
O50.98353 (19)0.2768 (2)0.1426 (2)0.0767 (8)
C50.4038 (5)0.9519 (4)0.0909 (4)0.0962 (15)
C60.3690 (4)0.8631 (4)0.0355 (4)0.0823 (12)
H6A0.29340.85800.02190.099*
O60.3615 (2)0.1907 (2)0.4513 (3)0.0923 (10)
C70.4419 (3)0.7802 (3)0.0013 (3)0.0644 (10)
H7A0.41510.72080.03850.077*
O70.02795 (18)0.08346 (19)0.38750 (19)0.0636 (7)
C80.6792 (3)0.5189 (2)0.0822 (3)0.0517 (8)
H8A0.71980.54060.12080.062*
O80.1754 (2)0.0138 (3)0.2580 (2)0.0911 (10)
C90.7636 (2)0.4594 (2)0.0191 (2)0.0462 (7)
O90.2008 (2)0.1666 (2)0.2895 (2)0.0786 (8)
C100.7348 (3)0.4320 (3)0.0546 (3)0.0550 (9)
H10A0.66390.45410.06900.066*
O100.2849 (2)0.2332 (3)0.6678 (2)0.0842 (9)
C110.8103 (3)0.3722 (3)0.1069 (3)0.0651 (10)
H11A0.78960.35440.15640.078*
C120.9168 (2)0.3378 (3)0.0877 (3)0.0550 (9)
C130.9486 (3)0.3677 (3)0.0166 (3)0.0632 (10)
H13A1.02010.34740.00350.076*
C140.8705 (3)0.4291 (3)0.0351 (3)0.0618 (9)
H14A0.89180.45030.08230.074*
C150.4143 (3)0.5126 (4)0.2970 (3)0.0760 (12)
H15A0.36800.49180.26250.091*
C160.3747 (5)0.6195 (5)0.2997 (5)0.1170 (19)
H16A0.37850.66090.23430.176*
H16B0.42090.64070.33200.176*
H16C0.29920.62550.33450.176*
C170.4119 (6)0.4438 (6)0.3946 (5)0.140 (2)
H17A0.43740.37630.38850.210*
H17B0.33710.44780.43140.210*
H17C0.45950.46220.42770.210*
C180.6608 (3)0.2496 (3)0.2166 (3)0.0709 (11)
H18A0.64880.25200.15180.085*
C190.5788 (5)0.1938 (4)0.2909 (5)0.124 (2)
H19A0.50520.22520.28180.186*
H19B0.58800.19370.35450.186*
H19C0.58950.12600.28520.186*
C200.7770 (4)0.2024 (4)0.2251 (5)0.122 (2)
H20A0.82810.24070.17490.183*
H20B0.78790.13500.21800.183*
H20C0.78980.20110.28790.183*
C211.0901 (3)0.2388 (5)0.1218 (4)0.1077 (18)
H21A1.12880.19670.16430.162*
H21B1.08370.20020.05520.162*
H21C1.13060.29350.13160.162*
C220.3224 (6)1.0398 (4)0.1290 (6)0.149 (3)
H22A0.24841.02250.10670.224*
H22B0.33921.05740.19910.224*
H22C0.32761.09590.10570.224*
C320.1632 (3)0.0901 (3)0.5589 (3)0.0721 (12)
H32A0.09310.07310.56490.086*
C240.2062 (3)0.2782 (3)0.5246 (3)0.0597 (9)
C340.2810 (3)0.1747 (3)0.6079 (3)0.0624 (9)
C350.3702 (3)0.1407 (3)0.5440 (3)0.0639 (10)
H35A0.44060.15680.53860.077*
C330.1773 (3)0.1485 (4)0.6153 (3)0.0782 (13)
H33A0.11670.17060.65880.094*
C290.1018 (3)0.2839 (3)0.5090 (3)0.0752 (11)
H29A0.06240.22780.47350.090*
C250.2597 (4)0.3628 (4)0.5797 (4)0.0933 (15)
H25A0.32960.36080.59050.112*
C270.1138 (6)0.4590 (4)0.6033 (4)0.1123 (19)
C400.1482 (4)0.2670 (3)0.2820 (4)0.0864 (13)
H40A0.08760.26830.33860.104*
C280.0569 (5)0.3729 (4)0.5465 (5)0.1047 (17)
H28A0.01180.37650.53420.126*
C430.3887 (4)0.2620 (4)0.6653 (4)0.0995 (16)
H43A0.37880.30250.71070.149*
H43B0.41630.30000.60070.149*
H43C0.44100.20310.68300.149*
C420.2333 (6)0.3271 (5)0.2858 (7)0.152 (3)
H42A0.26010.29960.34590.229*
H42B0.20000.39560.28210.229*
H42C0.29430.32470.23180.229*
C260.2137 (7)0.4490 (4)0.6187 (4)0.116 (2)
H26A0.25210.50320.65740.139*
C370.1099 (4)0.0422 (4)0.2348 (4)0.1015 (17)
H37A0.04670.05660.28880.122*
C380.1784 (9)0.1388 (5)0.2208 (6)0.193 (4)
H38A0.20580.17460.27930.289*
H38B0.23990.12510.16750.289*
H38C0.13340.17890.20660.289*
C410.1017 (7)0.3054 (6)0.1941 (6)0.166 (3)
H41A0.04660.26540.19620.248*
H41B0.15980.30250.13820.248*
H41C0.06780.37380.18990.248*
C440.0581 (8)0.5530 (5)0.6473 (6)0.179 (4)
H44A0.10630.60440.68350.269*
H44B0.04340.57600.59600.269*
H44C0.01070.53800.69010.269*
C390.0687 (9)0.0138 (8)0.1473 (8)0.202 (4)
H39A0.02150.07370.15880.304*
H39B0.02700.02670.12980.304*
H39C0.13030.03150.09520.304*
C300.2356 (2)0.0021 (3)0.4265 (3)0.0536 (8)
H30A0.30880.01780.38710.064*
C310.2520 (3)0.0561 (3)0.4933 (2)0.0523 (8)
C230.2607 (3)0.1856 (3)0.4811 (3)0.0603 (9)
C360.3538 (3)0.0825 (3)0.4882 (3)0.0624 (10)
H36A0.41460.06000.44510.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0486 (5)0.0586 (6)0.0503 (5)0.0021 (4)0.0198 (4)0.0141 (4)
N10.0504 (15)0.0487 (16)0.0650 (17)0.0026 (12)0.0260 (13)0.0193 (14)
C10.061 (2)0.048 (2)0.087 (3)0.0059 (17)0.026 (2)0.0163 (19)
O10.105 (2)0.080 (2)0.213 (4)0.0052 (18)0.099 (3)0.049 (2)
O20.0510 (12)0.0623 (15)0.0600 (14)0.0056 (11)0.0191 (11)0.0131 (12)
C20.065 (2)0.0392 (19)0.072 (2)0.0051 (16)0.0234 (18)0.0160 (18)
P20.0508 (5)0.0632 (6)0.0555 (6)0.0126 (4)0.0074 (4)0.0133 (5)
N20.0352 (13)0.0492 (16)0.0709 (18)0.0023 (12)0.0046 (12)0.0112 (14)
O30.0563 (14)0.0921 (19)0.0739 (17)0.0027 (13)0.0116 (12)0.0423 (15)
C30.090 (3)0.058 (3)0.132 (4)0.014 (2)0.017 (3)0.003 (3)
O40.0776 (16)0.0635 (17)0.0567 (15)0.0014 (13)0.0327 (12)0.0068 (13)
C40.149 (5)0.052 (3)0.131 (5)0.023 (3)0.027 (4)0.006 (3)
O50.0500 (14)0.098 (2)0.0844 (19)0.0083 (13)0.0195 (13)0.0336 (17)
C50.129 (4)0.064 (3)0.090 (3)0.017 (3)0.038 (3)0.018 (3)
C60.075 (3)0.079 (3)0.091 (3)0.017 (2)0.032 (2)0.024 (3)
O60.0475 (15)0.089 (2)0.137 (3)0.0119 (14)0.0110 (16)0.044 (2)
C70.064 (2)0.058 (2)0.069 (2)0.0051 (18)0.0203 (18)0.0152 (19)
O70.0480 (13)0.0694 (16)0.0711 (16)0.0115 (11)0.0142 (11)0.0093 (13)
C80.0491 (18)0.0483 (19)0.064 (2)0.0021 (15)0.0311 (16)0.0108 (17)
O80.0774 (18)0.127 (3)0.086 (2)0.0213 (18)0.0065 (16)0.055 (2)
C90.0367 (15)0.0476 (18)0.0548 (19)0.0049 (13)0.0165 (13)0.0079 (15)
O90.0662 (16)0.0706 (19)0.0833 (19)0.0164 (14)0.0048 (14)0.0021 (15)
C100.0402 (16)0.067 (2)0.065 (2)0.0009 (15)0.0262 (16)0.0196 (19)
O100.0582 (15)0.119 (2)0.092 (2)0.0230 (15)0.0044 (14)0.055 (2)
C110.0476 (18)0.088 (3)0.071 (2)0.0031 (18)0.0211 (17)0.033 (2)
C120.0394 (17)0.064 (2)0.059 (2)0.0008 (16)0.0118 (15)0.0132 (18)
C130.0423 (17)0.080 (3)0.067 (2)0.0062 (17)0.0240 (16)0.017 (2)
C140.0512 (19)0.078 (3)0.066 (2)0.0009 (17)0.0291 (17)0.024 (2)
C150.064 (2)0.102 (3)0.069 (3)0.009 (2)0.011 (2)0.037 (3)
C160.110 (4)0.120 (4)0.137 (5)0.021 (3)0.032 (4)0.074 (4)
C170.146 (5)0.149 (6)0.098 (4)0.017 (5)0.008 (4)0.016 (4)
C180.073 (2)0.074 (3)0.062 (2)0.007 (2)0.0171 (19)0.020 (2)
C190.126 (4)0.093 (4)0.142 (5)0.032 (4)0.003 (4)0.021 (4)
C200.097 (4)0.094 (4)0.144 (5)0.032 (3)0.024 (3)0.014 (4)
C210.062 (2)0.161 (5)0.092 (3)0.049 (3)0.027 (2)0.053 (4)
C220.194 (7)0.078 (4)0.163 (6)0.058 (4)0.087 (5)0.020 (4)
C320.0389 (18)0.119 (4)0.069 (2)0.024 (2)0.0019 (17)0.042 (3)
C240.071 (2)0.053 (2)0.051 (2)0.0067 (18)0.0120 (17)0.0166 (18)
C340.057 (2)0.073 (2)0.060 (2)0.0138 (18)0.0154 (17)0.014 (2)
C350.0405 (17)0.080 (3)0.075 (2)0.0179 (17)0.0078 (17)0.023 (2)
C330.0454 (19)0.125 (4)0.077 (3)0.015 (2)0.0028 (18)0.055 (3)
C290.073 (3)0.057 (2)0.085 (3)0.009 (2)0.011 (2)0.004 (2)
C250.119 (4)0.070 (3)0.097 (3)0.025 (3)0.056 (3)0.028 (3)
C270.161 (6)0.068 (3)0.096 (4)0.017 (4)0.010 (4)0.015 (3)
C400.077 (3)0.071 (3)0.106 (4)0.015 (2)0.021 (3)0.008 (3)
C280.100 (4)0.080 (4)0.128 (4)0.022 (3)0.005 (3)0.024 (3)
C430.092 (3)0.134 (4)0.100 (3)0.054 (3)0.016 (3)0.048 (3)
C420.135 (5)0.109 (5)0.229 (9)0.050 (4)0.067 (5)0.018 (5)
C260.201 (7)0.059 (3)0.086 (4)0.007 (4)0.060 (4)0.006 (3)
C370.096 (3)0.125 (4)0.096 (4)0.043 (3)0.006 (3)0.050 (3)
C380.321 (12)0.109 (5)0.152 (7)0.009 (6)0.014 (7)0.078 (5)
C410.182 (7)0.158 (6)0.152 (6)0.030 (5)0.102 (6)0.032 (5)
C440.253 (9)0.069 (4)0.182 (8)0.060 (5)0.012 (7)0.000 (4)
C390.235 (10)0.213 (10)0.202 (9)0.003 (8)0.149 (8)0.054 (8)
C300.0362 (15)0.058 (2)0.059 (2)0.0048 (14)0.0034 (14)0.0143 (17)
C310.0452 (17)0.056 (2)0.0528 (19)0.0090 (15)0.0106 (15)0.0064 (16)
C230.049 (2)0.068 (3)0.063 (2)0.0026 (18)0.0127 (17)0.022 (2)
C360.0383 (17)0.077 (3)0.071 (2)0.0113 (17)0.0067 (16)0.018 (2)
Geometric parameters (Å, º) top
P1—O21.470 (2)C19—H19A0.9600
P1—O41.560 (3)C19—H19B0.9600
P1—O31.582 (3)C19—H19C0.9600
P1—C81.820 (3)C20—H20A0.9600
N1—C11.343 (4)C20—H20B0.9600
N1—C81.466 (4)C20—H20C0.9600
N1—H1A0.8600C21—H21A0.9600
C1—O11.225 (4)C21—H21B0.9600
C1—C21.483 (5)C21—H21C0.9600
C2—C31.372 (6)C22—H22A0.9600
C2—C71.385 (5)C22—H22B0.9600
P2—O71.460 (2)C22—H22C0.9600
P2—O81.570 (3)C32—C331.374 (5)
P2—O91.561 (3)C32—C311.387 (5)
P2—C301.820 (4)C32—H32A0.9300
N2—C231.347 (4)C24—C251.376 (6)
N2—C301.457 (4)C24—C291.396 (5)
N2—H2A0.8600C24—C231.494 (5)
O3—C151.444 (4)C34—C331.387 (5)
C3—C41.398 (7)C34—C351.375 (5)
C3—H3A0.9300C35—C361.377 (5)
O4—C181.444 (5)C35—H35A0.9300
C4—C51.381 (8)C33—H33A0.9300
C4—H4A0.9300C29—C281.384 (6)
O5—C121.364 (4)C29—H29A0.9300
O5—C211.402 (5)C25—C261.357 (7)
C5—C61.367 (7)C25—H25A0.9300
C5—C221.498 (7)C27—C261.359 (8)
C6—C71.387 (5)C27—C281.420 (8)
C6—H6A0.9300C27—C441.518 (8)
O6—C231.225 (4)C40—C411.450 (8)
C7—H7A0.9300C40—C421.502 (7)
C8—C91.513 (5)C40—H40A0.9800
C8—H8A0.9800C28—H28A0.9300
O8—C371.392 (5)C43—H43A0.9600
C9—C101.380 (4)C43—H43B0.9600
C9—C141.373 (4)C43—H43C0.9600
O9—C401.417 (5)C42—H42A0.9600
C10—C111.374 (5)C42—H42B0.9600
C10—H10A0.9300C42—H42C0.9600
O10—C341.372 (4)C26—H26A0.9300
O10—C431.421 (5)C37—C391.444 (10)
C11—C121.388 (5)C37—C381.493 (9)
C11—H11A0.9300C37—H37A0.9800
C12—C131.384 (5)C38—H38A0.9600
C13—C141.397 (5)C38—H38B0.9600
C13—H13A0.9300C38—H38C0.9600
C14—H14A0.9300C41—H41A0.9600
C15—C171.471 (8)C41—H41B0.9600
C15—C161.492 (7)C41—H41C0.9600
C15—H15A0.9800C44—H44A0.9600
C16—H16A0.9600C44—H44B0.9600
C16—H16B0.9600C44—H44C0.9600
C16—H16C0.9600C39—H39A0.9600
C17—H17A0.9600C39—H39B0.9600
C17—H17B0.9600C39—H39C0.9600
C17—H17C0.9600C30—C311.506 (5)
C18—C191.463 (7)C30—H30A0.9800
C18—C201.489 (6)C31—C361.374 (4)
C18—H18A0.9800C36—H36A0.9300
O2—P1—O4115.52 (14)O5—C21—H21A109.5
O2—P1—O3116.31 (13)O5—C21—H21B109.5
O4—P1—O3103.65 (14)H21A—C21—H21B109.5
O2—P1—C8112.92 (14)O5—C21—H21C109.5
O4—P1—C8106.08 (14)H21A—C21—H21C109.5
O3—P1—C8100.76 (15)H21B—C21—H21C109.5
C1—N1—C8121.5 (3)C5—C22—H22A109.5
C1—N1—H1A119.3C5—C22—H22B109.5
C8—N1—H1A119.3H22A—C22—H22B109.5
O1—C1—N1122.2 (4)C5—C22—H22C109.5
O1—C1—C2121.5 (3)H22A—C22—H22C109.5
N1—C1—C2116.3 (3)H22B—C22—H22C109.5
C3—C2—C7118.7 (4)C33—C32—C31120.9 (3)
C3—C2—C1120.3 (4)C33—C32—H32A119.6
C7—C2—C1120.9 (3)C31—C32—H32A119.6
O7—P2—O8116.08 (15)C25—C24—C29117.6 (4)
O7—P2—O9117.14 (15)C25—C24—C23120.5 (4)
O8—P2—O9100.74 (17)C29—C24—C23121.9 (3)
O7—P2—C30113.59 (15)O10—C34—C33115.5 (3)
O8—P2—C30103.84 (17)O10—C34—C35125.3 (3)
O9—P2—C30103.56 (15)C33—C34—C35119.2 (3)
C23—N2—C30121.6 (3)C36—C35—C34119.0 (3)
C23—N2—H2A119.2C36—C35—H35A120.5
C30—N2—H2A119.2C34—C35—H35A120.5
C15—O3—P1124.0 (2)C32—C33—C34120.8 (3)
C2—C3—C4120.8 (5)C32—C33—H33A119.6
C2—C3—H3A119.6C34—C33—H33A119.6
C4—C3—H3A119.6C28—C29—C24120.0 (4)
C18—O4—P1124.5 (2)C28—C29—H29A120.0
C5—C4—C3120.8 (5)C24—C29—H29A120.0
C5—C4—H4A119.6C24—C25—C26122.1 (5)
C3—C4—H4A119.6C24—C25—H25A118.9
C12—O5—C21116.9 (3)C26—C25—H25A118.9
C6—C5—C4117.5 (4)C26—C27—C28116.6 (5)
C6—C5—C22121.0 (6)C26—C27—C44124.3 (7)
C4—C5—C22121.5 (6)C28—C27—C44119.1 (7)
C7—C6—C5122.6 (4)O9—C40—C41110.9 (5)
C7—C6—H6A118.7O9—C40—C42107.2 (4)
C5—C6—H6A118.7C41—C40—C42112.9 (5)
C6—C7—C2119.6 (4)O9—C40—H40A108.6
C6—C7—H7A120.2C41—C40—H40A108.6
C2—C7—H7A120.2C42—C40—H40A108.6
N1—C8—C9115.1 (3)C29—C28—C27121.2 (5)
N1—C8—P1107.4 (2)C29—C28—H28A119.4
C9—C8—P1111.9 (2)C27—C28—H28A119.4
N1—C8—H8A107.3O10—C43—H43A109.5
C9—C8—H8A107.3O10—C43—H43B109.5
P1—C8—H8A107.3H43A—C43—H43B109.5
C37—O8—P2128.1 (3)O10—C43—H43C109.5
C10—C9—C14118.2 (3)H43A—C43—H43C109.5
C10—C9—C8121.1 (3)H43B—C43—H43C109.5
C14—C9—C8120.7 (3)C40—C42—H42A109.5
C40—O9—P2126.3 (3)C40—C42—H42B109.5
C9—C10—C11120.3 (3)H42A—C42—H42B109.5
C9—C10—H10A119.9C40—C42—H42C109.5
C11—C10—H10A119.9H42A—C42—H42C109.5
C34—O10—C43118.7 (3)H42B—C42—H42C109.5
C10—C11—C12121.5 (3)C27—C26—C25122.4 (5)
C10—C11—H11A119.2C27—C26—H26A118.8
C12—C11—H11A119.2C25—C26—H26A118.8
O5—C12—C11116.3 (3)O8—C37—C39109.9 (6)
O5—C12—C13124.7 (3)O8—C37—C38108.8 (6)
C11—C12—C13119.0 (3)C39—C37—C38110.6 (6)
C14—C13—C12118.4 (3)O8—C37—H37A109.2
C14—C13—H13A120.8C39—C37—H37A109.2
C12—C13—H13A120.8C38—C37—H37A109.2
C13—C14—C9122.5 (3)C37—C38—H38A109.5
C13—C14—H14A118.7C37—C38—H38B109.5
C9—C14—H14A118.7H38A—C38—H38B109.5
O3—C15—C17110.2 (4)C37—C38—H38C109.5
O3—C15—C16106.0 (4)H38A—C38—H38C109.5
C17—C15—C16113.1 (5)H38B—C38—H38C109.5
O3—C15—H15A109.1C40—C41—H41A109.5
C17—C15—H15A109.1C40—C41—H41B109.5
C16—C15—H15A109.1H41A—C41—H41B109.5
C15—C16—H16A109.5C40—C41—H41C109.5
C15—C16—H16B109.5H41A—C41—H41C109.5
H16A—C16—H16B109.5H41B—C41—H41C109.5
C15—C16—H16C109.5C27—C44—H44A109.5
H16A—C16—H16C109.5C27—C44—H44B109.5
H16B—C16—H16C109.5H44A—C44—H44B109.5
C15—C17—H17A109.5C27—C44—H44C109.5
C15—C17—H17B109.5H44A—C44—H44C109.5
H17A—C17—H17B109.5H44B—C44—H44C109.5
C15—C17—H17C109.5C37—C39—H39A109.5
H17A—C17—H17C109.5C37—C39—H39B109.5
H17B—C17—H17C109.5H39A—C39—H39B109.5
O4—C18—C19109.4 (4)C37—C39—H39C109.5
O4—C18—C20108.3 (4)H39A—C39—H39C109.5
C19—C18—C20112.0 (5)H39B—C39—H39C109.5
O4—C18—H18A109.1N2—C30—C31115.4 (3)
C19—C18—H18A109.1N2—C30—P2107.5 (2)
C20—C18—H18A109.1C31—C30—P2113.2 (2)
C18—C19—H19A109.5N2—C30—H30A106.8
C18—C19—H19B109.5C31—C30—H30A106.8
H19A—C19—H19B109.5P2—C30—H30A106.8
C18—C19—H19C109.5C36—C31—C32117.1 (3)
H19A—C19—H19C109.5C36—C31—C30121.7 (3)
H19B—C19—H19C109.5C32—C31—C30121.1 (3)
C18—C20—H20A109.5O6—C23—N2122.3 (3)
C18—C20—H20B109.5O6—C23—C24121.1 (3)
H20A—C20—H20B109.5N2—C23—C24116.6 (3)
C18—C20—H20C109.5C31—C36—C35123.1 (3)
H20A—C20—H20C109.5C31—C36—H36A118.4
H20B—C20—H20C109.5C35—C36—H36A118.4
C8—N1—C1—O17.1 (6)C10—C9—C14—C133.5 (6)
C8—N1—C1—C2171.3 (3)C8—C9—C14—C13175.1 (3)
O1—C1—C2—C339.0 (6)P1—O3—C15—C1795.6 (5)
N1—C1—C2—C3142.5 (4)P1—O3—C15—C16141.7 (4)
O1—C1—C2—C7137.4 (4)P1—O4—C18—C1996.1 (4)
N1—C1—C2—C741.1 (5)P1—O4—C18—C20141.6 (4)
O2—P1—O3—C1528.2 (4)C43—O10—C34—C33179.2 (4)
O4—P1—O3—C1599.7 (3)C43—O10—C34—C350.1 (6)
C8—P1—O3—C15150.7 (3)O10—C34—C35—C36180.0 (4)
C7—C2—C3—C40.1 (7)C33—C34—C35—C360.7 (6)
C1—C2—C3—C4176.6 (5)C31—C32—C33—C340.1 (7)
O2—P1—O4—C1817.7 (3)O10—C34—C33—C32180.0 (4)
O3—P1—O4—C18146.2 (3)C35—C34—C33—C320.6 (7)
C8—P1—O4—C18108.2 (3)C25—C24—C29—C281.5 (6)
C2—C3—C4—C51.5 (9)C23—C24—C29—C28176.6 (4)
C3—C4—C5—C62.0 (9)C29—C24—C25—C260.5 (6)
C3—C4—C5—C22179.0 (6)C23—C24—C25—C26178.6 (4)
C4—C5—C6—C71.1 (7)P2—O9—C40—C4190.9 (5)
C22—C5—C6—C7179.8 (5)P2—O9—C40—C42145.5 (4)
C5—C6—C7—C20.3 (6)C24—C29—C28—C271.7 (7)
C3—C2—C7—C60.8 (6)C26—C27—C28—C290.0 (8)
C1—C2—C7—C6175.7 (4)C44—C27—C28—C29176.7 (5)
C1—N1—C8—C9109.7 (4)C28—C27—C26—C252.1 (9)
C1—N1—C8—P1124.9 (3)C44—C27—C26—C25178.6 (6)
O2—P1—C8—N155.7 (2)C24—C25—C26—C272.4 (8)
O4—P1—C8—N1176.9 (2)P2—O8—C37—C39105.7 (6)
O3—P1—C8—N169.1 (2)P2—O8—C37—C38133.0 (5)
O2—P1—C8—C971.6 (2)C23—N2—C30—C31102.7 (4)
O4—P1—C8—C955.8 (2)C23—N2—C30—P2130.1 (3)
O3—P1—C8—C9163.6 (2)O7—P2—C30—N255.0 (3)
O7—P2—O8—C3714.4 (5)O8—P2—C30—N272.0 (2)
O9—P2—O8—C37142.0 (4)O9—P2—C30—N2176.9 (2)
C30—P2—O8—C37111.0 (4)O7—P2—C30—C3173.5 (3)
N1—C8—C9—C1050.3 (4)O8—P2—C30—C31159.5 (2)
P1—C8—C9—C1072.7 (4)O9—P2—C30—C3154.6 (3)
N1—C8—C9—C14131.3 (3)C33—C32—C31—C360.6 (6)
P1—C8—C9—C14105.7 (3)C33—C32—C31—C30175.8 (4)
O7—P2—O9—C400.1 (4)N2—C30—C31—C36122.0 (4)
O8—P2—O9—C40126.8 (4)P2—C30—C31—C36113.7 (3)
C30—P2—O9—C40126.0 (4)N2—C30—C31—C3261.7 (4)
C14—C9—C10—C112.9 (5)P2—C30—C31—C3262.6 (4)
C8—C9—C10—C11175.6 (3)C30—N2—C23—O64.4 (6)
C9—C10—C11—C120.0 (6)C30—N2—C23—C24174.6 (3)
C21—O5—C12—C11178.0 (4)C25—C24—C23—O635.2 (5)
C21—O5—C12—C132.9 (6)C29—C24—C23—O6142.8 (4)
C10—C11—C12—O5178.4 (3)C25—C24—C23—N2145.7 (4)
C10—C11—C12—C132.5 (6)C29—C24—C23—N236.3 (5)
O5—C12—C13—C14179.0 (3)C32—C31—C36—C350.5 (6)
C11—C12—C13—C142.0 (6)C30—C31—C36—C35175.9 (4)
C12—C13—C14—C91.0 (6)C34—C35—C36—C310.2 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.862.203.021 (4)159
N2—H2A···O7ii0.862.203.013 (4)157
Symmetry codes: (i) x+1, y+1, z; (ii) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.862.203.021 (4)159
N2—H2A···O7ii0.862.203.013 (4)157
Symmetry codes: (i) x+1, y+1, z; (ii) x, y, z+1.
 

Acknowledgements

This work was supported by the Special Financial Fund of Innovative Development of the Marine Economic Demonstration Project, GD2012-D01–001, and the Public Science and Technology Research Funds Projects of the Ocean (grant Nos. 201205022–8 and 201405017)

References

First citationBruker (2001). SAINT, SMART and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationGiarda, L., Garbassi, F. & Calcaterra, M. (1973). Acta Cryst. B29, 1826–1829.  CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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