Diethyl phenyl(4-pyridyl­carbonyl­amino)­methyl­phospho­nate

Two mol­ecules of the title compound, C₁₇H₂₁N₂O₄P, are linked across a center of inversion by N—H...O=P amido–phospho­ryl interactions [d(N...O) = 2.894 (3) Å], forming a hydrogen-bonded dimer.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.072
• wR factor = 0.207
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.69 Ratio

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.97
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.71 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    P1     -   O4       =       5.99 su
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         P1
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C14
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C14    -   C15      =       1.42 Ang.
PLAT764_ALERT_4_C Overcomplete CIF Bond list Detected (Rep/Expd) .       1.36 Ratio

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Diethyl phenyl(4-pyridylcarbonylamino)methylphosphonate

Crystal data

C17H21N2O4P	F(000) = 1472
Mr = 348.33	Dx = 1.285 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4335 reflections
a = 23.714 (1) Å	θ = 2.3–27.5°
b = 8.0928 (4) Å	µ = 0.18 mm^−1
c = 20.012 (1) Å	T = 293 K
β = 110.325 (1)°	Block, colourless
V = 3601.4 (3) Å^3	0.35 × 0.27 × 0.26 mm
Z = 8

Data collection

Bruker APEX area-detector diffractometer	2774 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 25.0°, θmin = 1.8°
φ and ω scans	h = −28→28
12057 measured reflections	k = −9→9
3162 independent reflections	l = −23→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.207	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.1172P)^2 + 6.3036P] where P = (Fo^2 + 2Fc^2)/3
3162 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.95 e Å^−3
1 restraint	Δρmin = −0.32 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
P1	0.4453 (1)	0.4460 (1)	0.5871 (1)	0.0457 (3)
N1	0.7627 (2)	0.6298 (6)	0.6720 (3)	0.094 (1)
N2	0.5374 (1)	0.6483 (3)	0.6178 (1)	0.046 (1)
O2	0.5788 (1)	0.7240 (4)	0.7317 (1)	0.080 (1)
O3	0.4752 (1)	0.3332 (3)	0.6531 (1)	0.075 (1)
O4	0.3763 (1)	0.4501 (3)	0.5741 (2)	0.070 (1)
O5	0.4536 (1)	0.3961 (3)	0.5217 (1)	0.061 (1)
C1	0.6454 (1)	0.6638 (4)	0.6710 (2)	0.051 (1)
C2	0.6583 (2)	0.5617 (5)	0.6232 (2)	0.063 (1)
C3	0.7173 (2)	0.5495 (6)	0.6265 (2)	0.081 (1)
C4	0.7492 (2)	0.7287 (8)	0.7164 (3)	0.099 (2)
C5	0.6928 (2)	0.7497 (6)	0.7184 (2)	0.077 (1)
C6	0.5841 (1)	0.6831 (4)	0.6760 (2)	0.049 (1)
C7	0.4765 (1)	0.6489 (4)	0.6182 (2)	0.045 (1)
C8	0.4381 (1)	0.7884 (4)	0.5768 (2)	0.046 (1)
C9	0.4387 (2)	0.8348 (5)	0.5112 (2)	0.063 (1)
C10	0.4035 (2)	0.9637 (5)	0.4747 (2)	0.074 (1)
C11	0.3664 (2)	1.0452 (5)	0.5024 (2)	0.070 (1)
C12	0.3645 (2)	1.0003 (5)	0.5673 (2)	0.069 (1)
C13	0.4006 (2)	0.8727 (5)	0.6049 (2)	0.058 (1)
C14	0.5078 (2)	0.1842 (5)	0.6549 (2)	0.076 (1)
C15	0.5698 (2)	0.1977 (9)	0.6972 (3)	0.117 (2)
C16	0.3501 (2)	0.4646 (7)	0.6271 (3)	0.086 (1)
C17	0.2901 (2)	0.5394 (9)	0.5959 (3)	0.122 (2)
H1	0.543 (1)	0.630 (4)	0.5790 (9)	0.039 (8)*
H2	0.6281	0.5023	0.5896	0.076*
H3	0.7255	0.4795	0.5942	0.097*
H4	0.7804	0.7886	0.7486	0.118*
H5	0.6862	0.8211	0.7514	0.092*
H7	0.4788	0.6598	0.6679	0.054*
H9	0.4631	0.7786	0.4912	0.075*
H10	0.4051	0.9954	0.4307	0.088*
H11	0.3424	1.1313	0.4771	0.084*
H12	0.3390	1.0553	0.5862	0.083*
H13	0.3996	0.8434	0.6495	0.069*
H14a	0.4899	0.0960	0.6737	0.091*
H14b	0.5042	0.1546	0.6066	0.091*
H15a	0.5895	0.0945	0.6965	0.175*
H15b	0.5737	0.2245	0.7453	0.175*
H15c	0.5880	0.2832	0.6782	0.175*
H16a	0.3752	0.5330	0.6658	0.103*
H16b	0.3467	0.3563	0.6461	0.103*
H17a	0.2722	0.5498	0.6319	0.183*
H17b	0.2653	0.4704	0.5580	0.183*
H17c	0.2938	0.6467	0.5773	0.183*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.046 (1)	0.050 (1)	0.043 (1)	−0.003 (1)	0.017 (1)	0.003 (1)
N1	0.055 (2)	0.126 (4)	0.103 (3)	0.000 (2)	0.029 (2)	0.008 (3)
N2	0.044 (1)	0.060 (2)	0.036 (1)	−0.002 (1)	0.014 (1)	−0.004 (1)
O2	0.059 (2)	0.133 (3)	0.045 (1)	−0.008 (2)	0.015 (1)	−0.027 (2)
O3	0.102 (2)	0.067 (2)	0.058 (2)	0.019 (2)	0.031 (1)	0.010 (1)
O4	0.062 (2)	0.073 (2)	0.082 (2)	−0.012 (1)	0.032 (1)	−0.004 (1)
O5	0.072 (2)	0.065 (2)	0.047 (1)	−0.017 (1)	0.022 (1)	−0.008 (1)
C1	0.047 (2)	0.060 (2)	0.044 (2)	−0.001 (1)	0.012 (1)	0.008 (1)
C2	0.054 (2)	0.078 (3)	0.056 (2)	0.006 (2)	0.018 (2)	0.005 (2)
C3	0.069 (3)	0.102 (3)	0.078 (3)	0.017 (2)	0.034 (2)	0.008 (2)
C4	0.054 (2)	0.129 (4)	0.102 (4)	−0.022 (3)	0.013 (2)	−0.010 (3)
C5	0.053 (2)	0.097 (3)	0.073 (2)	−0.015 (2)	0.013 (2)	−0.015 (2)
C6	0.048 (2)	0.056 (2)	0.040 (2)	−0.002 (1)	0.011 (1)	−0.001 (1)
C7	0.044 (2)	0.056 (2)	0.036 (2)	−0.005 (1)	0.015 (1)	−0.002 (1)
C8	0.045 (2)	0.048 (2)	0.045 (2)	−0.009 (1)	0.015 (1)	−0.003 (1)
C9	0.072 (2)	0.066 (2)	0.056 (2)	0.008 (2)	0.029 (2)	0.006 (2)
C10	0.082 (3)	0.072 (3)	0.066 (2)	0.010 (2)	0.026 (2)	0.023 (2)
C11	0.060 (2)	0.055 (2)	0.086 (3)	0.004 (2)	0.014 (2)	0.016 (2)
C12	0.059 (2)	0.061 (2)	0.095 (3)	0.006 (2)	0.035 (2)	0.002 (2)
C13	0.055 (2)	0.062 (2)	0.062 (2)	−0.002 (2)	0.028 (2)	0.001 (2)
C14	0.088 (3)	0.064 (2)	0.065 (2)	0.008 (2)	0.014 (2)	0.004 (2)
C15	0.082 (3)	0.152 (6)	0.102 (4)	0.024 (3)	0.013 (3)	−0.016 (4)
C16	0.077 (3)	0.098 (3)	0.093 (3)	−0.011 (2)	0.043 (2)	−0.002 (3)
C17	0.065 (3)	0.174 (6)	0.141 (5)	0.014 (3)	0.053 (3)	0.003 (5)

Geometric parameters (Å, º)

P1—O3	1.559 (3)	C9—C10	1.377 (5)
P1—O4	1.565 (3)	C10—C11	1.362 (6)
P1—O5	1.448 (2)	C11—C12	1.364 (6)
P1—C7	1.819 (3)	C12—C13	1.385 (5)
N1—C3	1.314 (6)	C14—C15	1.424 (6)
N1—C4	1.314 (7)	C16—C17	1.470 (7)
N2—C6	1.330 (4)	N2—H1	0.84 (1)
N2—C7	1.447 (4)	C2—H2	0.93
O2—C6	1.210 (4)	C3—H3	0.93
O3—C14	1.425 (5)	C4—H4	0.93
O4—C16	1.407 (5)	C5—H5	0.93
C1—C2	1.375 (5)	C7—H7	0.98
C1—C5	1.380 (5)	C9—H9	0.93
C1—C6	1.500 (4)	C10—H10	0.93
C2—C3	1.381 (5)	C11—H11	0.93
C4—C5	1.364 (6)	C12—H12	0.93
C7—C8	1.506 (4)	C13—H13	0.93
C4—C5	1.364 (6)	C14—H14a	0.97
C7—C8	1.506 (4)	C14—H14b	0.97
C8—C13	1.386 (5)	C15—H15a	0.96
C9—C10	1.377 (5)	C15—H15b	0.96
C10—C11	1.362 (6)	C15—H15c	0.96
C11—C12	1.364 (6)	C16—H16a	0.97
C12—C13	1.385 (5)	C16—H16b	0.97
C14—C15	1.424 (6)	C17—H17a	0.96
C16—C17	1.470 (7)	C17—H17b	0.96
C8—C9	1.370 (5)	C17—H17c	0.96
C8—C13	1.386 (5)
O3—P1—O4	107.1 (2)	N1—C4—H4	117.7
O3—P1—O5	116.0 (2)	C5—C4—H4	117.7
O3—P1—C7	103.2 (2)	C4—C5—H5	120.3
O4—P1—O5	108.6 (2)	C1—C5—H5	120.3
O4—P1—C7	108.3 (1)	N2—C7—H7	107.5
O5—P1—C7	113.2 (1)	C8—C7—H7	107.5
C3—N1—C4	115.9 (4)	P1—C7—H7	107.5
C6—N2—C7	121.6 (3)	C8—C9—H9	119.7
C14—O3—P1	126.8 (3)	C10—C9—H9	119.7
C16—O4—P1	125.9 (3)	C11—C10—H10	119.7
C2—C1—C5	117.1 (3)	C9—C10—H10	119.7
C2—C1—C6	124.3 (3)	C10—C11—H11	120.0
C5—C1—C6	118.5 (3)	C12—C11—H11	120.0
C1—C2—C3	118.4 (4)	C11—C12—H12	120.1
N1—C3—C2	124.7 (4)	C13—C12—H12	120.1
N1—C4—C5	124.5 (5)	C12—C13—H13	119.7
C4—C5—C1	119.3 (4)	C8—C13—H13	119.7
O2—C6—N2	122.9 (3)	C15—C14—H14a	109.0
O2—C6—C1	120.2 (3)	O3—C14—H14a	109.0
N2—C6—C1	116.8 (3)	C15—C14—H14b	109.0
N2—C7—C8	114.4 (2)	O3—C14—H14b	109.0
N2—C7—P1	106.4 (2)	H14a—C14—H14b	107.8
C8—C7—P1	113.1 (2)	C14—C15—H15a	109.5
C9—C8—C13	118.4 (3)	C14—C15—H15b	109.5
C9—C8—C7	121.8 (3)	H15a—C15—H15b	109.5
C13—C8—C7	119.8 (3)	C14—C15—H15c	109.5
C8—C9—C10	120.7 (4)	H15a—C15—H15c	109.5
C11—C10—C9	120.6 (4)	H15b—C15—H15c	109.5
C10—C11—C12	119.9 (4)	O4—C16—H16a	109.8
C11—C12—C13	119.8 (4)	C17—C16—H16a	109.8
C12—C13—C8	120.6 (3)	O4—C16—H16b	109.8
C15—C14—O3	112.9 (4)	C17—C16—H16b	109.8
O4—C16—C17	109.2 (4)	H16a—C16—H16b	108.3
C6—N2—H1	120 (2)	C16—C17—H17a	109.5
C7—N2—H1	119 (2)	C16—C17—H17b	109.5
C1—C2—H2	120.8	H17a—C17—H17b	109.5
C3—C2—H2	120.8	C16—C17—H17c	109.5
N1—C3—H3	117.6	H17a—C17—H17c	109.5
C2—C3—H3	117.6	H17b—C17—H17c	109.5
O5—P1—O3—C14	−2.4 (4)	C6—N2—C7—P1	−124.1 (3)
O4—P1—O3—C14	119.1 (4)	O5—P1—C7—N2	−49.9 (2)
C7—P1—O3—C14	−126.7 (3)	O3—P1—C7—N2	76.3 (2)
O5—P1—O4—C16	168.3 (3)	O4—P1—C7—N2	−170.4 (2)
O3—P1—O4—C16	42.3 (4)	O5—P1—C7—C8	76.5 (2)
C7—P1—O4—C16	−68.3 (4)	O3—P1—C7—C8	−157.3 (2)
C5—C1—C2—C3	1.1 (5)	O4—P1—C7—C8	−44.0 (2)
C6—C1—C2—C3	−176.9 (3)	N2—C7—C8—C9	43.0 (4)
C4—N1—C3—C2	−0.6 (8)	P1—C7—C8—C9	−79.1 (3)
C1—C2—C3—N1	−0.5 (7)	N2—C7—C8—C13	−137.3 (3)
C3—N1—C4—C5	1.1 (8)	P1—C7—C8—C13	100.6 (3)
N1—C4—C5—C1	−0.5 (8)	C13—C8—C9—C10	0.9 (5)
C2—C1—C5—C4	−0.6 (6)	C7—C8—C9—C10	−179.4 (3)
C6—C1—C5—C4	177.5 (4)	C8—C9—C10—C11	−1.4 (6)
C7—N2—C6—O2	−3.3 (5)	C9—C10—C11—C12	0.8 (7)
C7—N2—C6—C1	174.6 (3)	C10—C11—C12—C13	0.4 (6)
C2—C1—C6—O2	153.6 (4)	C11—C12—C13—C8	−1.0 (6)
C5—C1—C6—O2	−24.3 (5)	C9—C8—C13—C12	0.3 (5)
C2—C1—C6—N2	−24.4 (5)	C7—C8—C13—C12	−179.4 (3)
C5—C1—C6—N2	157.6 (3)	P1—O3—C14—C15	113.8 (4)
C6—N2—C7—C8	110.2 (3)	P1—O4—C16—C17	153.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O5^i	0.84 (1)	2.06 (1)	2.894 (3)	173 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.