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Hydrogen-bond inter­actions in the title compound, C20H29N2O8P, generate infinite ribbons consisting of alternating centrosymmetric R22(8) and R22(16) rings. Within the ribbons, the P=O bonds are anti­parallel, making the crystal structure non-polar.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806034374/ci2153sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806034374/ci2153Isup2.hkl
Contains datablock I

CCDC reference: 624165

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.038
  • wR factor = 0.089
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT and SADABS (Bruker, 2005); program(s) used to solve structure: SIR92 (Burla et al., 1989); program(s) used to refine structure: LS in TEXSAN (Molecular Structure Corporation, 1997) and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and SHELXTL (Bruker, 2005); software used to prepare material for publication: SHELXL97 and PLATON.

Ethyl N,N'-bis(3,4,5-trimethoxyphenyl)phosphorodiamidate top
Crystal data top
C20H29N2O8PZ = 2
Mr = 456.42F(000) = 484
Triclinic, P1Dx = 1.419 Mg m3
Hall symbol: -P 1Melting point = 434–436 K
a = 10.0994 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.1542 (5) ÅCell parameters from 6224 reflections
c = 11.9800 (9) Åθ = 2.4–26.2°
α = 93.596 (3)°µ = 0.18 mm1
β = 98.968 (3)°T = 100 K
γ = 117.066 (2)°Irregular fragment, colorless
V = 1068.10 (11) Å30.26 × 0.20 × 0.20 mm
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer
4358 independent reflections
Radiation source: X-ray tube3628 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
φ and ω scansθmax = 26.4°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1212
Tmin = 0.862, Tmax = 0.965k = 1212
31960 measured reflectionsl = 1414
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0355P)2 + 0.7048P]
where P = (Fo2 + 2Fc2)/3
4358 reflections(Δ/σ)max = 0.001
295 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.44 e Å3
Special details top

Experimental. RF = 0.58 (CH2Cl2/CH3OH = 95/10). 1H NMR (300 MHz, CDCl3, δ, p.p.m.): 7.86 (d, J = 9.0 Hz, 2H), 6.41 (s, 4H), 4.06 (p, J = 6.9 Hz, 2H), 3.69 (s, 12H), 3.56 (s, 6H), 1.29 (t, J = 6.9 Hz, 3H). 13C NMR (75 MHz, CDCl3, δ, p.p.m.): 153.7, 138.3, 132.3, 96.0, 61.6, 60.8, 56.4, 16.9.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P10.07938 (5)0.16365 (4)0.65742 (4)0.01396 (12)
O10.28320 (13)0.76472 (12)0.58531 (10)0.0194 (3)
O20.44494 (13)0.78872 (12)0.42249 (10)0.0186 (3)
O30.44492 (13)0.54698 (12)0.31786 (10)0.0175 (3)
O40.12345 (13)0.09481 (13)1.02950 (10)0.0225 (3)
O50.39598 (13)0.08991 (13)1.16382 (9)0.0184 (3)
O60.60601 (13)0.31568 (13)1.08376 (10)0.0197 (3)
O70.03594 (12)0.26332 (12)0.73463 (9)0.0160 (3)
O80.03119 (13)0.00310 (12)0.64092 (10)0.0176 (3)
N10.09461 (15)0.22411 (15)0.53471 (12)0.0149 (3)
N20.25175 (16)0.20541 (15)0.72458 (12)0.0166 (3)
C10.18692 (17)0.37029 (17)0.51126 (13)0.0132 (3)
C20.18984 (18)0.49540 (17)0.56800 (14)0.0152 (3)
H2A0.13320.48570.62610.018*
C30.27686 (18)0.63521 (17)0.53859 (14)0.0149 (3)
C40.36392 (18)0.65141 (17)0.45542 (14)0.0152 (3)
C50.35817 (17)0.52395 (17)0.39916 (14)0.0140 (3)
C60.26837 (17)0.38304 (17)0.42577 (14)0.0138 (3)
H60.26290.29640.38570.017*
C70.1920 (2)0.75411 (19)0.66762 (15)0.0203 (4)
H7A0.08570.68250.63430.030*
H7B0.20030.85250.68990.030*
H7C0.22740.72000.73520.030*
C80.58594 (19)0.88588 (18)0.50146 (15)0.0203 (4)
H8A0.56710.89050.57910.030*
H8B0.62840.98650.48020.030*
H8C0.65810.84670.49880.030*
C90.4421 (2)0.41705 (18)0.26117 (15)0.0203 (4)
H9A0.47340.36590.31800.031*
H9B0.51220.44710.20840.031*
H9C0.33890.34920.21830.031*
C100.28850 (18)0.17349 (17)0.83475 (14)0.0149 (3)
C110.43198 (18)0.26501 (17)0.90260 (14)0.0157 (3)
H110.50470.34750.87490.019*
C120.46766 (18)0.23443 (17)1.01131 (14)0.0157 (3)
C130.36178 (19)0.11490 (18)1.05361 (14)0.0159 (3)
C140.21974 (19)0.02222 (18)0.98284 (14)0.0170 (4)
C150.18226 (18)0.05054 (18)0.87404 (14)0.0166 (4)
H150.08530.01300.82670.020*
C160.71306 (19)0.4481 (2)1.04916 (16)0.0241 (4)
H16A0.74310.42110.98090.036*
H16B0.80300.50151.11110.036*
H16C0.66670.51271.03170.036*
C170.45407 (19)0.01527 (19)1.16731 (15)0.0202 (4)
H17A0.37900.11001.11940.030*
H17B0.47430.03251.24630.030*
H17C0.54860.02471.13870.030*
C180.0143 (2)0.20325 (19)0.95506 (16)0.0250 (4)
H18A0.07180.15390.92250.038*
H18B0.07520.27920.99830.038*
H18C0.00980.25110.89330.038*
C190.12383 (18)0.23059 (19)0.71416 (15)0.0192 (4)
H19A0.18680.13360.73830.023*
H19B0.16230.22490.63180.023*
C200.1313 (2)0.3555 (2)0.78301 (16)0.0238 (4)
H20A0.09250.36020.86420.036*
H20B0.23690.33670.77160.036*
H20C0.06920.45060.75800.036*
H10.074 (2)0.155 (2)0.4806 (18)0.029 (6)*
H20.321 (2)0.259 (2)0.6962 (18)0.029 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0155 (2)0.0124 (2)0.0130 (2)0.00527 (17)0.00392 (16)0.00347 (16)
O10.0277 (6)0.0122 (5)0.0210 (6)0.0100 (5)0.0102 (5)0.0021 (5)
O20.0216 (6)0.0112 (5)0.0193 (6)0.0045 (5)0.0038 (5)0.0051 (5)
O30.0214 (6)0.0137 (6)0.0188 (6)0.0074 (5)0.0101 (5)0.0042 (5)
O40.0191 (6)0.0217 (6)0.0202 (7)0.0030 (5)0.0044 (5)0.0107 (5)
O50.0240 (6)0.0217 (6)0.0127 (6)0.0133 (5)0.0037 (5)0.0042 (5)
O60.0162 (6)0.0198 (6)0.0176 (6)0.0049 (5)0.0002 (5)0.0021 (5)
O70.0142 (5)0.0164 (6)0.0161 (6)0.0063 (5)0.0029 (5)0.0015 (5)
O80.0188 (6)0.0140 (6)0.0161 (6)0.0040 (5)0.0044 (5)0.0036 (5)
N10.0185 (7)0.0109 (7)0.0128 (7)0.0047 (6)0.0035 (6)0.0019 (6)
N20.0157 (7)0.0168 (7)0.0156 (8)0.0052 (6)0.0051 (6)0.0071 (6)
C10.0134 (7)0.0125 (7)0.0118 (8)0.0050 (6)0.0002 (6)0.0040 (6)
C20.0168 (8)0.0154 (8)0.0134 (8)0.0073 (7)0.0040 (6)0.0030 (6)
C30.0185 (8)0.0125 (7)0.0136 (8)0.0080 (7)0.0007 (6)0.0013 (6)
C40.0169 (8)0.0108 (7)0.0163 (9)0.0055 (6)0.0010 (7)0.0051 (6)
C50.0145 (8)0.0165 (8)0.0117 (8)0.0075 (7)0.0029 (6)0.0053 (6)
C60.0165 (8)0.0118 (7)0.0134 (8)0.0077 (6)0.0011 (6)0.0016 (6)
C70.0246 (9)0.0201 (8)0.0184 (9)0.0117 (7)0.0070 (7)0.0011 (7)
C80.0183 (8)0.0140 (8)0.0254 (10)0.0050 (7)0.0043 (7)0.0034 (7)
C90.0250 (9)0.0185 (8)0.0209 (9)0.0111 (7)0.0108 (7)0.0035 (7)
C100.0178 (8)0.0152 (8)0.0146 (9)0.0098 (7)0.0043 (7)0.0034 (6)
C110.0159 (8)0.0121 (7)0.0188 (9)0.0057 (6)0.0049 (7)0.0029 (6)
C120.0164 (8)0.0149 (8)0.0157 (9)0.0081 (7)0.0023 (7)0.0010 (6)
C130.0198 (8)0.0193 (8)0.0123 (8)0.0121 (7)0.0041 (7)0.0030 (6)
C140.0181 (8)0.0157 (8)0.0191 (9)0.0078 (7)0.0086 (7)0.0063 (7)
C150.0142 (8)0.0164 (8)0.0172 (9)0.0056 (7)0.0025 (7)0.0034 (7)
C160.0170 (8)0.0220 (9)0.0234 (10)0.0018 (7)0.0021 (7)0.0014 (7)
C170.0213 (9)0.0220 (9)0.0201 (9)0.0122 (7)0.0048 (7)0.0060 (7)
C180.0206 (9)0.0184 (9)0.0275 (10)0.0014 (7)0.0053 (8)0.0077 (7)
C190.0146 (8)0.0217 (9)0.0200 (9)0.0078 (7)0.0030 (7)0.0032 (7)
C200.0230 (9)0.0278 (9)0.0226 (10)0.0133 (8)0.0058 (7)0.0050 (8)
Geometric parameters (Å, º) top
P1—O81.4757 (11)C7—H7C0.98
P1—O71.5765 (12)C8—H8A0.98
P1—N11.6308 (14)C8—H8B0.98
P1—N21.6451 (15)C8—H8C0.98
O1—C31.3662 (19)C9—H9A0.98
O1—C71.428 (2)C9—H9B0.98
O2—C41.3786 (18)C9—H9C0.98
O2—C81.442 (2)C10—C111.392 (2)
O3—C51.3708 (19)C10—C151.394 (2)
O3—C91.4320 (19)C11—C121.389 (2)
O4—C141.3680 (19)C11—H110.95
O4—C181.428 (2)C12—C131.392 (2)
O5—C131.381 (2)C13—C141.398 (2)
O5—C171.433 (2)C14—C151.385 (2)
O6—C121.3672 (19)C15—H150.95
O6—C161.427 (2)C16—H16A0.98
O7—C191.4673 (19)C16—H16B0.98
N1—C11.4233 (19)C16—H16C0.98
N1—H10.85 (2)C17—H17A0.98
N2—C101.413 (2)C17—H17B0.98
N2—H20.80 (2)C17—H17C0.98
C1—C61.387 (2)C18—H18A0.98
C1—C21.389 (2)C18—H18B0.98
C2—C31.391 (2)C18—H18C0.98
C2—H2A0.95C19—C201.506 (2)
C3—C41.398 (2)C19—H19A0.99
C4—C51.394 (2)C19—H19B0.99
C5—C61.392 (2)C20—H20A0.98
C6—H60.95C20—H20B0.98
C7—H7A0.98C20—H20C0.98
C7—H7B0.98
O8—P1—O7112.74 (6)O3—C9—H9C109.5
O8—P1—N1110.68 (7)H9A—C9—H9C109.5
O7—P1—N1108.58 (7)H9B—C9—H9C109.5
O8—P1—N2114.49 (7)C11—C10—C15120.67 (15)
O7—P1—N2102.90 (7)C11—C10—N2119.25 (14)
N1—P1—N2106.96 (7)C15—C10—N2120.07 (14)
C3—O1—C7117.43 (13)C12—C11—C10119.26 (15)
C4—O2—C8113.89 (12)C12—C11—H11120.4
C5—O3—C9116.47 (12)C10—C11—H11120.4
C14—O4—C18116.83 (13)O6—C12—C11123.83 (14)
C13—O5—C17111.66 (12)O6—C12—C13115.13 (15)
C12—O6—C16117.20 (13)C11—C12—C13121.04 (15)
C19—O7—P1117.61 (10)O5—C13—C12120.52 (14)
C1—N1—P1129.34 (12)O5—C13—C14120.80 (14)
C1—N1—H1113.3 (14)C12—C13—C14118.67 (15)
P1—N1—H1112.5 (14)O4—C14—C15123.72 (15)
C10—N2—P1124.98 (12)O4—C14—C13115.18 (15)
C10—N2—H2117.8 (15)C15—C14—C13121.10 (15)
P1—N2—H2116.5 (15)C14—C15—C10119.21 (15)
C6—C1—C2120.96 (14)C14—C15—H15120.4
C6—C1—N1117.74 (14)C10—C15—H15120.4
C2—C1—N1121.24 (14)O6—C16—H16A109.5
C1—C2—C3119.08 (15)O6—C16—H16B109.5
C1—C2—H2A120.5H16A—C16—H16B109.5
C3—C2—H2A120.5O6—C16—H16C109.5
O1—C3—C2124.06 (15)H16A—C16—H16C109.5
O1—C3—C4114.97 (14)H16B—C16—H16C109.5
C2—C3—C4120.96 (14)O5—C17—H17A109.5
O2—C4—C5119.91 (14)O5—C17—H17B109.5
O2—C4—C3121.09 (14)H17A—C17—H17B109.5
C5—C4—C3118.81 (14)O5—C17—H17C109.5
O3—C5—C6123.25 (14)H17A—C17—H17C109.5
O3—C5—C4116.05 (14)H17B—C17—H17C109.5
C6—C5—C4120.70 (15)O4—C18—H18A109.5
C1—C6—C5119.44 (15)O4—C18—H18B109.5
C1—C6—H6120.3H18A—C18—H18B109.5
C5—C6—H6120.3O4—C18—H18C109.5
O1—C7—H7A109.5H18A—C18—H18C109.5
O1—C7—H7B109.5H18B—C18—H18C109.5
H7A—C7—H7B109.5O7—C19—C20107.33 (13)
O1—C7—H7C109.5O7—C19—H19A110.2
H7A—C7—H7C109.5C20—C19—H19A110.2
H7B—C7—H7C109.5O7—C19—H19B110.2
O2—C8—H8A109.5C20—C19—H19B110.2
O2—C8—H8B109.5H19A—C19—H19B108.5
H8A—C8—H8B109.5C19—C20—H20A109.5
O2—C8—H8C109.5C19—C20—H20B109.5
H8A—C8—H8C109.5H20A—C20—H20B109.5
H8B—C8—H8C109.5C19—C20—H20C109.5
O3—C9—H9A109.5H20A—C20—H20C109.5
O3—C9—H9B109.5H20B—C20—H20C109.5
H9A—C9—H9B109.5
O8—P1—O7—C1943.07 (13)C2—C1—C6—C52.1 (2)
N1—P1—O7—C1979.95 (12)N1—C1—C6—C5179.05 (14)
N2—P1—O7—C19166.92 (11)O3—C5—C6—C1178.45 (14)
O8—P1—N1—C1179.76 (13)C4—C5—C6—C11.6 (2)
O7—P1—N1—C155.50 (16)P1—N2—C10—C11151.83 (13)
N2—P1—N1—C154.91 (16)P1—N2—C10—C1528.9 (2)
O8—P1—N2—C1057.67 (15)C15—C10—C11—C121.3 (2)
O7—P1—N2—C1065.02 (14)N2—C10—C11—C12179.44 (15)
N1—P1—N2—C10179.32 (13)C16—O6—C12—C116.7 (2)
P1—N1—C1—C6133.69 (14)C16—O6—C12—C13173.79 (15)
P1—N1—C1—C249.4 (2)C10—C11—C12—O6178.77 (15)
C6—C1—C2—C30.4 (2)C10—C11—C12—C130.7 (2)
N1—C1—C2—C3177.26 (14)C17—O5—C13—C1294.24 (18)
C7—O1—C3—C21.3 (2)C17—O5—C13—C1486.64 (18)
C7—O1—C3—C4177.68 (14)O6—C12—C13—O53.7 (2)
C1—C2—C3—O1177.20 (15)C11—C12—C13—O5176.85 (14)
C1—C2—C3—C41.8 (2)O6—C12—C13—C14177.20 (14)
C8—O2—C4—C5106.40 (17)C11—C12—C13—C142.3 (2)
C8—O2—C4—C378.76 (19)C18—O4—C14—C158.7 (2)
O1—C3—C4—O21.9 (2)C18—O4—C14—C13171.80 (15)
C2—C3—C4—O2177.11 (14)O5—C13—C14—O42.4 (2)
O1—C3—C4—C5176.84 (14)C12—C13—C14—O4178.44 (14)
C2—C3—C4—C52.2 (2)O5—C13—C14—C15177.11 (15)
C9—O3—C5—C61.3 (2)C12—C13—C14—C152.0 (3)
C9—O3—C5—C4178.81 (14)O4—C14—C15—C10179.64 (15)
O2—C4—C5—O34.5 (2)C13—C14—C15—C100.2 (3)
C3—C4—C5—O3179.42 (14)C11—C10—C15—C141.5 (2)
O2—C4—C5—C6175.45 (14)N2—C10—C15—C14179.19 (15)
C3—C4—C5—C60.5 (2)P1—O7—C19—C20170.39 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O8i0.85 (2)1.94 (2)2.7904 (18)179 (3)
N2—H2···O3ii0.81 (2)2.33 (2)3.099 (2)160 (2)
C8—H8B···O1iii0.982.493.470 (2)175
C9—H9B···O6iv0.982.503.270 (2)135
C16—H16B···O7v0.982.603.459 (2)147
Symmetry codes: (i) x, y, z+1; (ii) x+1, y+1, z+1; (iii) x+1, y+2, z+1; (iv) x, y, z1; (v) x+1, y+1, z+2.
 

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