Ethyl N,N′-bis­(3,4,5-trimethoxy­phen­yl)phospho­rodiamidate

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.

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

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Computing details

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

Crystal data

C20H29N2O8P	Z = 2
Mr = 456.42	F(000) = 484
Triclinic, P1	Dx = 1.419 Mg m^−3
Hall symbol: -P 1	Melting point = 434–436 K
a = 10.0994 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.1542 (5) Å	Cell parameters from 6224 reflections
c = 11.9800 (9) Å	θ = 2.4–26.2°
α = 93.596 (3)°	µ = 0.18 mm^−1
β = 98.968 (3)°	T = 100 K
γ = 117.066 (2)°	Irregular fragment, colorless
V = 1068.10 (11) Å^3	0.26 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer	4358 independent reflections
Radiation source: X-ray tube	3628 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 26.4°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
Tmin = 0.862, Tmax = 0.965	k = −12→12
31960 measured reflections	l = −14→14

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0355P)^2 + 0.7048P] where P = (Fo^2 + 2Fc^2)/3
4358 reflections	(Δ/σ)max = 0.001
295 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.44 e Å^−3

Special details

Experimental. R_F = 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 (Ų)

	x	y	z	Uiso*/Ueq
P1	0.07938 (5)	0.16365 (4)	0.65742 (4)	0.01396 (12)
O1	0.28320 (13)	0.76472 (12)	0.58531 (10)	0.0194 (3)
O2	0.44494 (13)	0.78872 (12)	0.42249 (10)	0.0186 (3)
O3	0.44492 (13)	0.54698 (12)	0.31786 (10)	0.0175 (3)
O4	0.12345 (13)	−0.09481 (13)	1.02950 (10)	0.0225 (3)
O5	0.39598 (13)	0.08991 (13)	1.16382 (9)	0.0184 (3)
O6	0.60601 (13)	0.31568 (13)	1.08376 (10)	0.0197 (3)
O7	0.03594 (12)	0.26332 (12)	0.73463 (9)	0.0160 (3)
O8	−0.03119 (13)	0.00310 (12)	0.64092 (10)	0.0176 (3)
N1	0.09461 (15)	0.22411 (15)	0.53471 (12)	0.0149 (3)
N2	0.25175 (16)	0.20541 (15)	0.72458 (12)	0.0166 (3)
C1	0.18692 (17)	0.37029 (17)	0.51126 (13)	0.0132 (3)
C2	0.18984 (18)	0.49540 (17)	0.56800 (14)	0.0152 (3)
H2A	0.1332	0.4857	0.6261	0.018*
C3	0.27686 (18)	0.63521 (17)	0.53859 (14)	0.0149 (3)
C4	0.36392 (18)	0.65141 (17)	0.45542 (14)	0.0152 (3)
C5	0.35817 (17)	0.52395 (17)	0.39916 (14)	0.0140 (3)
C6	0.26837 (17)	0.38304 (17)	0.42577 (14)	0.0138 (3)
H6	0.2629	0.2964	0.3857	0.017*
C7	0.1920 (2)	0.75411 (19)	0.66762 (15)	0.0203 (4)
H7A	0.0857	0.6825	0.6343	0.030*
H7B	0.2003	0.8525	0.6899	0.030*
H7C	0.2274	0.7200	0.7352	0.030*
C8	0.58594 (19)	0.88588 (18)	0.50146 (15)	0.0203 (4)
H8A	0.5671	0.8905	0.5791	0.030*
H8B	0.6284	0.9865	0.4802	0.030*
H8C	0.6581	0.8467	0.4988	0.030*
C9	0.4421 (2)	0.41705 (18)	0.26117 (15)	0.0203 (4)
H9A	0.4734	0.3659	0.3180	0.031*
H9B	0.5122	0.4471	0.2084	0.031*
H9C	0.3389	0.3492	0.2183	0.031*
C10	0.28850 (18)	0.17349 (17)	0.83475 (14)	0.0149 (3)
C11	0.43198 (18)	0.26501 (17)	0.90260 (14)	0.0157 (3)
H11	0.5047	0.3475	0.8749	0.019*
C12	0.46766 (18)	0.23443 (17)	1.01131 (14)	0.0157 (3)
C13	0.36178 (19)	0.11490 (18)	1.05361 (14)	0.0159 (3)
C14	0.21974 (19)	0.02222 (18)	0.98284 (14)	0.0170 (4)
C15	0.18226 (18)	0.05054 (18)	0.87404 (14)	0.0166 (4)
H15	0.0853	−0.0130	0.8267	0.020*
C16	0.71306 (19)	0.4481 (2)	1.04916 (16)	0.0241 (4)
H16A	0.7431	0.4211	0.9809	0.036*
H16B	0.8030	0.5015	1.1111	0.036*
H16C	0.6667	0.5127	1.0317	0.036*
C17	0.45407 (19)	−0.01527 (19)	1.16731 (15)	0.0202 (4)
H17A	0.3790	−0.1100	1.1194	0.030*
H17B	0.4743	−0.0325	1.2463	0.030*
H17C	0.5486	0.0247	1.1387	0.030*
C18	−0.0143 (2)	−0.20325 (19)	0.95506 (16)	0.0250 (4)
H18A	−0.0718	−0.1539	0.9225	0.038*
H18B	−0.0752	−0.2792	0.9983	0.038*
H18C	0.0098	−0.2511	0.8933	0.038*
C19	−0.12383 (18)	0.23059 (19)	0.71416 (15)	0.0192 (4)
H19A	−0.1868	0.1336	0.7383	0.023*
H19B	−0.1623	0.2249	0.6318	0.023*
C20	−0.1313 (2)	0.3555 (2)	0.78301 (16)	0.0238 (4)
H20A	−0.0925	0.3602	0.8642	0.036*
H20B	−0.2369	0.3367	0.7716	0.036*
H20C	−0.0692	0.4506	0.7580	0.036*
H1	0.074 (2)	0.155 (2)	0.4806 (18)	0.029 (6)*
H2	0.321 (2)	0.259 (2)	0.6962 (18)	0.029 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0155 (2)	0.0124 (2)	0.0130 (2)	0.00527 (17)	0.00392 (16)	0.00347 (16)
O1	0.0277 (6)	0.0122 (5)	0.0210 (6)	0.0100 (5)	0.0102 (5)	0.0021 (5)
O2	0.0216 (6)	0.0112 (5)	0.0193 (6)	0.0045 (5)	0.0038 (5)	0.0051 (5)
O3	0.0214 (6)	0.0137 (6)	0.0188 (6)	0.0074 (5)	0.0101 (5)	0.0042 (5)
O4	0.0191 (6)	0.0217 (6)	0.0202 (7)	0.0030 (5)	0.0044 (5)	0.0107 (5)
O5	0.0240 (6)	0.0217 (6)	0.0127 (6)	0.0133 (5)	0.0037 (5)	0.0042 (5)
O6	0.0162 (6)	0.0198 (6)	0.0176 (6)	0.0049 (5)	0.0002 (5)	0.0021 (5)
O7	0.0142 (5)	0.0164 (6)	0.0161 (6)	0.0063 (5)	0.0029 (5)	0.0015 (5)
O8	0.0188 (6)	0.0140 (6)	0.0161 (6)	0.0040 (5)	0.0044 (5)	0.0036 (5)
N1	0.0185 (7)	0.0109 (7)	0.0128 (7)	0.0047 (6)	0.0035 (6)	0.0019 (6)
N2	0.0157 (7)	0.0168 (7)	0.0156 (8)	0.0052 (6)	0.0051 (6)	0.0071 (6)
C1	0.0134 (7)	0.0125 (7)	0.0118 (8)	0.0050 (6)	−0.0002 (6)	0.0040 (6)
C2	0.0168 (8)	0.0154 (8)	0.0134 (8)	0.0073 (7)	0.0040 (6)	0.0030 (6)
C3	0.0185 (8)	0.0125 (7)	0.0136 (8)	0.0080 (7)	0.0007 (6)	0.0013 (6)
C4	0.0169 (8)	0.0108 (7)	0.0163 (9)	0.0055 (6)	0.0010 (7)	0.0051 (6)
C5	0.0145 (8)	0.0165 (8)	0.0117 (8)	0.0075 (7)	0.0029 (6)	0.0053 (6)
C6	0.0165 (8)	0.0118 (7)	0.0134 (8)	0.0077 (6)	0.0011 (6)	0.0016 (6)
C7	0.0246 (9)	0.0201 (8)	0.0184 (9)	0.0117 (7)	0.0070 (7)	0.0011 (7)
C8	0.0183 (8)	0.0140 (8)	0.0254 (10)	0.0050 (7)	0.0043 (7)	0.0034 (7)
C9	0.0250 (9)	0.0185 (8)	0.0209 (9)	0.0111 (7)	0.0108 (7)	0.0035 (7)
C10	0.0178 (8)	0.0152 (8)	0.0146 (9)	0.0098 (7)	0.0043 (7)	0.0034 (6)
C11	0.0159 (8)	0.0121 (7)	0.0188 (9)	0.0057 (6)	0.0049 (7)	0.0029 (6)
C12	0.0164 (8)	0.0149 (8)	0.0157 (9)	0.0081 (7)	0.0023 (7)	−0.0010 (6)
C13	0.0198 (8)	0.0193 (8)	0.0123 (8)	0.0121 (7)	0.0041 (7)	0.0030 (6)
C14	0.0181 (8)	0.0157 (8)	0.0191 (9)	0.0078 (7)	0.0086 (7)	0.0063 (7)
C15	0.0142 (8)	0.0164 (8)	0.0172 (9)	0.0056 (7)	0.0025 (7)	0.0034 (7)
C16	0.0170 (8)	0.0220 (9)	0.0234 (10)	0.0018 (7)	0.0021 (7)	0.0014 (7)
C17	0.0213 (9)	0.0220 (9)	0.0201 (9)	0.0122 (7)	0.0048 (7)	0.0060 (7)
C18	0.0206 (9)	0.0184 (9)	0.0275 (10)	0.0014 (7)	0.0053 (8)	0.0077 (7)
C19	0.0146 (8)	0.0217 (9)	0.0200 (9)	0.0078 (7)	0.0030 (7)	0.0032 (7)
C20	0.0230 (9)	0.0278 (9)	0.0226 (10)	0.0133 (8)	0.0058 (7)	0.0050 (8)

Geometric parameters (Å, º)

P1—O8	1.4757 (11)	C7—H7C	0.98
P1—O7	1.5765 (12)	C8—H8A	0.98
P1—N1	1.6308 (14)	C8—H8B	0.98
P1—N2	1.6451 (15)	C8—H8C	0.98
O1—C3	1.3662 (19)	C9—H9A	0.98
O1—C7	1.428 (2)	C9—H9B	0.98
O2—C4	1.3786 (18)	C9—H9C	0.98
O2—C8	1.442 (2)	C10—C11	1.392 (2)
O3—C5	1.3708 (19)	C10—C15	1.394 (2)
O3—C9	1.4320 (19)	C11—C12	1.389 (2)
O4—C14	1.3680 (19)	C11—H11	0.95
O4—C18	1.428 (2)	C12—C13	1.392 (2)
O5—C13	1.381 (2)	C13—C14	1.398 (2)
O5—C17	1.433 (2)	C14—C15	1.385 (2)
O6—C12	1.3672 (19)	C15—H15	0.95
O6—C16	1.427 (2)	C16—H16A	0.98
O7—C19	1.4673 (19)	C16—H16B	0.98
N1—C1	1.4233 (19)	C16—H16C	0.98
N1—H1	0.85 (2)	C17—H17A	0.98
N2—C10	1.413 (2)	C17—H17B	0.98
N2—H2	0.80 (2)	C17—H17C	0.98
C1—C6	1.387 (2)	C18—H18A	0.98
C1—C2	1.389 (2)	C18—H18B	0.98
C2—C3	1.391 (2)	C18—H18C	0.98
C2—H2A	0.95	C19—C20	1.506 (2)
C3—C4	1.398 (2)	C19—H19A	0.99
C4—C5	1.394 (2)	C19—H19B	0.99
C5—C6	1.392 (2)	C20—H20A	0.98
C6—H6	0.95	C20—H20B	0.98
C7—H7A	0.98	C20—H20C	0.98
C7—H7B	0.98
O8—P1—O7	112.74 (6)	O3—C9—H9C	109.5
O8—P1—N1	110.68 (7)	H9A—C9—H9C	109.5
O7—P1—N1	108.58 (7)	H9B—C9—H9C	109.5
O8—P1—N2	114.49 (7)	C11—C10—C15	120.67 (15)
O7—P1—N2	102.90 (7)	C11—C10—N2	119.25 (14)
N1—P1—N2	106.96 (7)	C15—C10—N2	120.07 (14)
C3—O1—C7	117.43 (13)	C12—C11—C10	119.26 (15)
C4—O2—C8	113.89 (12)	C12—C11—H11	120.4
C5—O3—C9	116.47 (12)	C10—C11—H11	120.4
C14—O4—C18	116.83 (13)	O6—C12—C11	123.83 (14)
C13—O5—C17	111.66 (12)	O6—C12—C13	115.13 (15)
C12—O6—C16	117.20 (13)	C11—C12—C13	121.04 (15)
C19—O7—P1	117.61 (10)	O5—C13—C12	120.52 (14)
C1—N1—P1	129.34 (12)	O5—C13—C14	120.80 (14)
C1—N1—H1	113.3 (14)	C12—C13—C14	118.67 (15)
P1—N1—H1	112.5 (14)	O4—C14—C15	123.72 (15)
C10—N2—P1	124.98 (12)	O4—C14—C13	115.18 (15)
C10—N2—H2	117.8 (15)	C15—C14—C13	121.10 (15)
P1—N2—H2	116.5 (15)	C14—C15—C10	119.21 (15)
C6—C1—C2	120.96 (14)	C14—C15—H15	120.4
C6—C1—N1	117.74 (14)	C10—C15—H15	120.4
C2—C1—N1	121.24 (14)	O6—C16—H16A	109.5
C1—C2—C3	119.08 (15)	O6—C16—H16B	109.5
C1—C2—H2A	120.5	H16A—C16—H16B	109.5
C3—C2—H2A	120.5	O6—C16—H16C	109.5
O1—C3—C2	124.06 (15)	H16A—C16—H16C	109.5
O1—C3—C4	114.97 (14)	H16B—C16—H16C	109.5
C2—C3—C4	120.96 (14)	O5—C17—H17A	109.5
O2—C4—C5	119.91 (14)	O5—C17—H17B	109.5
O2—C4—C3	121.09 (14)	H17A—C17—H17B	109.5
C5—C4—C3	118.81 (14)	O5—C17—H17C	109.5
O3—C5—C6	123.25 (14)	H17A—C17—H17C	109.5
O3—C5—C4	116.05 (14)	H17B—C17—H17C	109.5
C6—C5—C4	120.70 (15)	O4—C18—H18A	109.5
C1—C6—C5	119.44 (15)	O4—C18—H18B	109.5
C1—C6—H6	120.3	H18A—C18—H18B	109.5
C5—C6—H6	120.3	O4—C18—H18C	109.5
O1—C7—H7A	109.5	H18A—C18—H18C	109.5
O1—C7—H7B	109.5	H18B—C18—H18C	109.5
H7A—C7—H7B	109.5	O7—C19—C20	107.33 (13)
O1—C7—H7C	109.5	O7—C19—H19A	110.2
H7A—C7—H7C	109.5	C20—C19—H19A	110.2
H7B—C7—H7C	109.5	O7—C19—H19B	110.2
O2—C8—H8A	109.5	C20—C19—H19B	110.2
O2—C8—H8B	109.5	H19A—C19—H19B	108.5
H8A—C8—H8B	109.5	C19—C20—H20A	109.5
O2—C8—H8C	109.5	C19—C20—H20B	109.5
H8A—C8—H8C	109.5	H20A—C20—H20B	109.5
H8B—C8—H8C	109.5	C19—C20—H20C	109.5
O3—C9—H9A	109.5	H20A—C20—H20C	109.5
O3—C9—H9B	109.5	H20B—C20—H20C	109.5
H9A—C9—H9B	109.5
O8—P1—O7—C19	−43.07 (13)	C2—C1—C6—C5	2.1 (2)
N1—P1—O7—C19	79.95 (12)	N1—C1—C6—C5	179.05 (14)
N2—P1—O7—C19	−166.92 (11)	O3—C5—C6—C1	178.45 (14)
O8—P1—N1—C1	179.76 (13)	C4—C5—C6—C1	−1.6 (2)
O7—P1—N1—C1	55.50 (16)	P1—N2—C10—C11	−151.83 (13)
N2—P1—N1—C1	−54.91 (16)	P1—N2—C10—C15	28.9 (2)
O8—P1—N2—C10	−57.67 (15)	C15—C10—C11—C12	−1.3 (2)
O7—P1—N2—C10	65.02 (14)	N2—C10—C11—C12	179.44 (15)
N1—P1—N2—C10	179.32 (13)	C16—O6—C12—C11	6.7 (2)
P1—N1—C1—C6	133.69 (14)	C16—O6—C12—C13	−173.79 (15)
P1—N1—C1—C2	−49.4 (2)	C10—C11—C12—O6	178.77 (15)
C6—C1—C2—C3	−0.4 (2)	C10—C11—C12—C13	−0.7 (2)
N1—C1—C2—C3	−177.26 (14)	C17—O5—C13—C12	−94.24 (18)
C7—O1—C3—C2	−1.3 (2)	C17—O5—C13—C14	86.64 (18)
C7—O1—C3—C4	177.68 (14)	O6—C12—C13—O5	3.7 (2)
C1—C2—C3—O1	177.20 (15)	C11—C12—C13—O5	−176.85 (14)
C1—C2—C3—C4	−1.8 (2)	O6—C12—C13—C14	−177.20 (14)
C8—O2—C4—C5	−106.40 (17)	C11—C12—C13—C14	2.3 (2)
C8—O2—C4—C3	78.76 (19)	C18—O4—C14—C15	8.7 (2)
O1—C3—C4—O2	−1.9 (2)	C18—O4—C14—C13	−171.80 (15)
C2—C3—C4—O2	177.11 (14)	O5—C13—C14—O4	−2.4 (2)
O1—C3—C4—C5	−176.84 (14)	C12—C13—C14—O4	178.44 (14)
C2—C3—C4—C5	2.2 (2)	O5—C13—C14—C15	177.11 (15)
C9—O3—C5—C6	−1.3 (2)	C12—C13—C14—C15	−2.0 (3)
C9—O3—C5—C4	178.81 (14)	O4—C14—C15—C10	179.64 (15)
O2—C4—C5—O3	4.5 (2)	C13—C14—C15—C10	0.2 (3)
C3—C4—C5—O3	179.42 (14)	C11—C10—C15—C14	1.5 (2)
O2—C4—C5—C6	−175.45 (14)	N2—C10—C15—C14	−179.19 (15)
C3—C4—C5—C6	−0.5 (2)	P1—O7—C19—C20	−170.39 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O8^i	0.85 (2)	1.94 (2)	2.7904 (18)	179 (3)
N2—H2···O3^ii	0.81 (2)	2.33 (2)	3.099 (2)	160 (2)
C8—H8B···O1^iii	0.98	2.49	3.470 (2)	175
C9—H9B···O6^iv	0.98	2.50	3.270 (2)	135
C16—H16B···O7^v	0.98	2.60	3.459 (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, z−1; (v) −x+1, −y+1, −z+2.