Dimethyl hydrazine-1,2-dicarboxyl-ate-triphenyl-phosphine oxide (1/1).

In the crystal structure of the title compound, C(4)H(8)N(2)O(4)·C(18)H(15)OP, two triphenyl-phosphine oxide mol-ecules and two dimethyl hydrazine-1,2-dicarboxyl-ate mol-ecules are connected via N-H⋯O hydrogen bonds of moderate strength and are related via a twofold rotational axis. Weak C(ar)-H⋯ O contacts strengthen the crystal structure.

Related literature

For the Mitsunobu reaction, see: Mitsunobu (1981 ▶); Hughes (1992 ▶), Swamy et al. (2009 ▶). For the structures of analogous compounds, see: Anderson et al. (1996 ▶); Héroux & Brisse (1997 ▶); Wang et al. (2007 ▶). For the synthesis of this and related compounds, see Doboszewski (1997 ▶, 2009 ▶).

Experimental

Crystal data

C4H8N2O4·C18H15OP

M = 426.39

Monoclinic,

a = 26.494 (3) Å

b = 8.5545 (9) Å

c = 20.4426 (19) Å

β = 109.090 (3)°

V = 4378.3 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.16 mm−1

T = 200 K

0.8 × 0.7 × 0.4 mm

Data collection

Bruker SMART X2S diffractometer

Absorption correction: multi-scan (SADABS (Sheldrick, 2008a ▶) T min = 0.84, T max = 0.93

20468 measured reflections

3862 independent reflections

2956 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.095

S = 1.03

3862 reflections

298 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.30 e Å−3

Data collection: GIS (Bruker, 2010 ▶); cell refinement: APEX2 (Bruker, 2010 ▶) and SAINT (Bruker, 2009 ▶); data reduction: SAINT and XPREP (Bruker, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681101991X/mw2011sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681101991X/mw2011Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681101991X/mw2011Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Enhanced figure: interactive version of Fig. 3

C4H8N2O4·C18H15OP	F(000) = 1792
Mr = 426.39	Dx = 1.294 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3730 reflections
a = 26.494 (3) Å	θ = 2.5–24.4°
b = 8.5545 (9) Å	µ = 0.16 mm−1
c = 20.4426 (19) Å	T = 200 K
β = 109.090 (3)°	Prism, colourless
V = 4378.3 (8) Å3	0.8 × 0.7 × 0.4 mm
Z = 8

Bruker SMART X2S diffractometer	3862 independent reflections
Radiation source: XOS X-beam microfocus source	2956 reflections with I > 2σ(I)
doubly curved silicon crystal	Rint = 0.036
ω scans	θmax = 25.1°, θmin = 2.5°
Absorption correction: multi-scan (SADABS (Sheldrick, 2008a)	h = −31→31
Tmin = 0.84, Tmax = 0.93	k = −10→10
20468 measured reflections	l = −24→24

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0533P)2] where P = (Fo2 + 2Fc2)/3
3862 reflections	(Δ/σ)max = 0.001
298 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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.

	x	y	z	Uiso*/Ueq
P1	0.149303 (17)	0.57905 (5)	0.87467 (2)	0.02544 (14)
O1	−0.00845 (5)	0.79421 (15)	0.65671 (7)	0.0488 (4)
O2	0.07350 (5)	0.70178 (15)	0.66494 (6)	0.0447 (3)
O3	0.08693 (5)	0.23349 (15)	0.65300 (7)	0.0476 (4)
O4	0.01686 (5)	0.35822 (15)	0.57612 (6)	0.0451 (3)
O5	0.10118 (4)	0.50237 (13)	0.82537 (5)	0.0294 (3)
N1	0.00680 (6)	0.54291 (18)	0.67207 (8)	0.0378 (4)
H1	−0.0244 (8)	0.535 (2)	0.6754 (10)	0.048 (6)*
N2	0.03969 (6)	0.41275 (18)	0.68918 (8)	0.0372 (4)
H2	0.0640 (7)	0.419 (2)	0.7272 (10)	0.036 (5)*
C1	0.00936 (10)	0.9500 (2)	0.65050 (13)	0.0638 (7)
H1C	−0.0205 (4)	1.0138 (9)	0.6276 (8)	0.096*
H1B	0.0332 (6)	0.9482 (3)	0.6246 (8)	0.096*
H1A	0.0271 (6)	0.9911 (9)	0.6953 (6)	0.096*
C2	0.02861 (7)	0.6822 (2)	0.66519 (8)	0.0351 (4)
C3	0.05118 (7)	0.3283 (2)	0.63982 (9)	0.0349 (4)
C4	0.02347 (10)	0.2626 (3)	0.52124 (11)	0.0646 (7)
H4C	0.0053 (6)	0.3099 (11)	0.4776 (6)	0.097*
H4B	0.0089 (6)	0.1613 (14)	0.5229 (5)	0.097*
H4A	0.0606 (5)	0.2535 (15)	0.5269 (5)	0.097*
C11	0.16370 (7)	0.50014 (18)	0.96079 (8)	0.0281 (4)
C12	0.12062 (8)	0.4739 (2)	0.98395 (10)	0.0405 (5)
H12A	0.0857 (7)	0.4938 (5)	0.9542 (6)	0.049*
C13	0.12841 (9)	0.4190 (2)	1.04989 (10)	0.0486 (5)
H13A	0.0996 (6)	0.4028 (4)	1.0647 (3)	0.058*
C14	0.17909 (9)	0.3886 (2)	1.09350 (11)	0.0517 (6)
H14A	0.18455 (16)	0.3523 (9)	1.1397 (11)	0.062*
C15	0.22194 (9)	0.4102 (3)	1.07079 (11)	0.0575 (6)
H15A	0.2541 (8)	0.3883 (6)	1.0982 (7)	0.069*
C16	0.21459 (8)	0.4665 (2)	1.00490 (9)	0.0425 (5)
H16A	0.2438 (6)	0.4818 (4)	0.9902 (3)	0.051*
C21	0.14139 (6)	0.78746 (18)	0.88138 (8)	0.0268 (4)
C22	0.13023 (7)	0.8756 (2)	0.82090 (10)	0.0350 (4)
H22A	0.12774 (8)	0.8242 (10)	0.7772 (8)	0.042*
C23	0.12265 (8)	1.0355 (2)	0.82236 (11)	0.0422 (5)
H23A	0.11515 (17)	1.0970 (12)	0.7799 (9)	0.051*
C24	0.12570 (8)	1.1079 (2)	0.88404 (11)	0.0473 (5)
H24A	0.12009 (15)	1.216 (2)	0.88489 (11)	0.057*
C25	0.13689 (8)	1.0227 (2)	0.94401 (11)	0.0457 (5)
H25A	0.13925 (9)	1.0737 (11)	0.9865 (9)	0.055*
C26	0.14479 (7)	0.8620 (2)	0.94297 (10)	0.0352 (4)
H26A	0.15250 (16)	0.8033 (11)	0.9845 (8)	0.042*
C31	0.20790 (7)	0.55624 (18)	0.84924 (8)	0.0276 (4)
C32	0.20893 (8)	0.4427 (2)	0.80066 (9)	0.0392 (5)
H32A	0.1776 (6)	0.3766 (13)	0.7795 (4)	0.047*
C33	0.25459 (8)	0.4243 (3)	0.78255 (11)	0.0515 (6)
H33A	0.25523 (9)	0.3520 (18)	0.7511 (8)	0.062*
C34	0.29896 (8)	0.5155 (3)	0.81221 (10)	0.0477 (5)
H34A	0.3296 (7)	0.5006 (4)	0.8003 (3)	0.057*
C35	0.29792 (8)	0.6288 (2)	0.85965 (10)	0.0423 (5)
H35A	0.3295 (6)	0.6949 (14)	0.8805 (4)	0.051*
C36	0.25267 (7)	0.6494 (2)	0.87778 (9)	0.0352 (4)
H36A	0.25208 (7)	0.7255 (16)	0.9091 (6)	0.042*

	U11	U22	U33	U12	U13	U23
P1	0.0270 (2)	0.0250 (2)	0.0231 (3)	−0.00232 (18)	0.00640 (19)	−0.00216 (18)
O1	0.0400 (8)	0.0444 (8)	0.0621 (9)	0.0031 (6)	0.0167 (7)	0.0007 (7)
O2	0.0374 (8)	0.0594 (9)	0.0420 (8)	−0.0045 (6)	0.0192 (6)	−0.0049 (6)
O3	0.0497 (8)	0.0438 (8)	0.0514 (9)	0.0081 (7)	0.0195 (7)	0.0000 (6)
O4	0.0513 (8)	0.0565 (9)	0.0254 (7)	0.0014 (7)	0.0097 (6)	−0.0057 (6)
O5	0.0281 (6)	0.0295 (6)	0.0275 (6)	−0.0044 (5)	0.0049 (5)	−0.0050 (5)
N1	0.0282 (9)	0.0469 (10)	0.0385 (10)	0.0018 (7)	0.0113 (7)	−0.0041 (7)
N2	0.0327 (9)	0.0480 (10)	0.0259 (9)	0.0065 (7)	0.0026 (8)	−0.0050 (7)
C1	0.0649 (16)	0.0467 (14)	0.0768 (17)	−0.0003 (11)	0.0192 (13)	0.0018 (12)
C2	0.0311 (10)	0.0512 (12)	0.0218 (10)	0.0021 (9)	0.0070 (8)	−0.0043 (8)
C3	0.0353 (10)	0.0372 (11)	0.0337 (11)	−0.0056 (9)	0.0132 (9)	−0.0016 (8)
C4	0.0955 (19)	0.0660 (15)	0.0359 (13)	−0.0054 (13)	0.0262 (12)	−0.0144 (11)
C11	0.0327 (10)	0.0237 (9)	0.0267 (10)	−0.0028 (7)	0.0082 (8)	−0.0032 (7)
C12	0.0400 (11)	0.0510 (12)	0.0321 (11)	0.0040 (9)	0.0139 (9)	0.0054 (9)
C13	0.0553 (14)	0.0582 (14)	0.0403 (13)	0.0019 (10)	0.0267 (11)	0.0055 (10)
C14	0.0726 (17)	0.0516 (13)	0.0304 (12)	−0.0028 (11)	0.0164 (11)	0.0101 (9)
C15	0.0484 (13)	0.0737 (16)	0.0383 (13)	0.0008 (11)	−0.0024 (10)	0.0208 (11)
C16	0.0356 (11)	0.0528 (13)	0.0358 (12)	−0.0052 (9)	0.0072 (9)	0.0093 (9)
C21	0.0253 (9)	0.0258 (9)	0.0281 (10)	−0.0024 (7)	0.0069 (7)	−0.0027 (7)
C22	0.0389 (11)	0.0325 (10)	0.0332 (11)	−0.0022 (8)	0.0111 (8)	0.0003 (8)
C23	0.0470 (12)	0.0315 (10)	0.0449 (12)	−0.0027 (8)	0.0107 (9)	0.0071 (9)
C24	0.0483 (13)	0.0252 (10)	0.0635 (15)	−0.0010 (8)	0.0114 (11)	−0.0041 (10)
C25	0.0508 (13)	0.0366 (11)	0.0453 (12)	−0.0017 (9)	0.0096 (10)	−0.0170 (10)
C26	0.0385 (10)	0.0324 (10)	0.0310 (10)	−0.0018 (8)	0.0064 (8)	−0.0052 (8)
C31	0.0301 (9)	0.0279 (9)	0.0234 (9)	0.0005 (7)	0.0071 (7)	0.0016 (7)
C32	0.0411 (11)	0.0403 (11)	0.0368 (11)	−0.0021 (9)	0.0136 (9)	−0.0076 (9)
C33	0.0575 (14)	0.0564 (14)	0.0464 (13)	0.0051 (11)	0.0251 (11)	−0.0156 (10)
C34	0.0407 (12)	0.0643 (14)	0.0453 (13)	0.0059 (10)	0.0241 (10)	0.0021 (11)
C35	0.0348 (11)	0.0546 (12)	0.0391 (12)	−0.0064 (9)	0.0142 (9)	0.0012 (10)
C36	0.0375 (11)	0.0391 (10)	0.0306 (10)	−0.0042 (8)	0.0131 (8)	−0.0052 (8)

P1—O5	1.4938 (11)	C14—C15	1.373 (3)
P1—C31	1.8017 (17)	C14—H14A	0.9582
P1—C21	1.8056 (16)	C15—C16	1.383 (3)
P1—C11	1.8058 (17)	C15—H15A	0.8729
O1—C2	1.342 (2)	C16—H16A	0.9271
O1—C1	1.433 (2)	C21—C26	1.388 (2)
O2—C2	1.203 (2)	C21—C22	1.395 (2)
O3—C3	1.209 (2)	C22—C23	1.384 (2)
O4—C3	1.347 (2)	C22—H22A	0.9782
O4—C4	1.445 (2)	C23—C24	1.383 (3)
N1—C2	1.352 (2)	C23—H23A	0.9780
N1—N2	1.386 (2)	C24—C25	1.373 (3)
N1—H1	0.85 (2)	C24—H24A	0.9379
N2—C3	1.354 (2)	C25—C26	1.391 (2)
N2—H2	0.832 (18)	C25—H25A	0.9546
C1—H1C	0.9492	C26—H26A	0.9485
C1—H1B	0.9492	C31—C36	1.389 (2)
C1—H1A	0.9492	C31—C32	1.396 (2)
C4—H4C	0.9539	C32—C33	1.385 (3)
C4—H4B	0.9539	C32—H32A	0.9810
C4—H4A	0.9539	C33—C34	1.375 (3)
C11—C16	1.385 (2)	C33—H33A	0.8962
C11—C12	1.389 (2)	C34—C35	1.378 (3)
C12—C13	1.378 (3)	C34—H34A	0.9307
C12—H12A	0.9422	C35—C36	1.377 (2)
C13—C14	1.372 (3)	C35—H35A	0.9830
C13—H13A	0.9187	C36—H36A	0.9161
O5—P1—C31	112.56 (7)	C15—C14—H14A	120.1
O5—P1—C21	112.97 (7)	C14—C15—C16	120.5 (2)
C31—P1—C21	105.14 (7)	C14—C15—H15A	119.7
O5—P1—C11	110.80 (7)	C16—C15—H15A	119.7
C31—P1—C11	108.28 (8)	C15—C16—C11	120.22 (19)
C21—P1—C11	106.73 (8)	C15—C16—H16A	119.9
C2—O1—C1	115.29 (16)	C11—C16—H16A	119.9
C3—O4—C4	115.36 (16)	C26—C21—C22	119.19 (16)
C2—N1—N2	118.65 (16)	C26—C21—P1	123.23 (13)
C2—N1—H1	122.3 (13)	C22—C21—P1	117.57 (13)
N2—N1—H1	117.6 (13)	C23—C22—C21	120.35 (18)
C3—N2—N1	121.10 (16)	C23—C22—H22A	119.8
C3—N2—H2	115.9 (12)	C21—C22—H22A	119.8
N1—N2—H2	114.3 (12)	C24—C23—C22	119.80 (19)
O1—C1—H1C	109.5	C24—C23—H23A	120.1
O1—C1—H1B	109.5	C22—C23—H23A	120.1
H1C—C1—H1B	109.5	C25—C24—C23	120.46 (19)
O1—C1—H1A	109.5	C25—C24—H24A	119.8
H1C—C1—H1A	109.5	C23—C24—H24A	119.8
H1B—C1—H1A	109.5	C24—C25—C26	120.04 (19)
O2—C2—O1	125.67 (18)	C24—C25—H25A	120.0
O2—C2—N1	125.44 (18)	C26—C25—H25A	120.0
O1—C2—N1	108.86 (15)	C21—C26—C25	120.16 (18)
O3—C3—O4	125.12 (17)	C21—C26—H26A	119.9
O3—C3—N2	122.87 (17)	C25—C26—H26A	119.9
O4—C3—N2	111.95 (16)	C36—C31—C32	119.02 (17)
O4—C4—H4C	109.5	C36—C31—P1	120.98 (13)
O4—C4—H4B	109.5	C32—C31—P1	120.00 (13)
H4C—C4—H4B	109.5	C33—C32—C31	119.46 (18)
O4—C4—H4A	109.5	C33—C32—H32A	120.3
H4C—C4—H4A	109.5	C31—C32—H32A	120.3
H4B—C4—H4A	109.5	C34—C33—C32	120.84 (19)
C16—C11—C12	118.54 (16)	C34—C33—H33A	119.6
C16—C11—P1	124.23 (14)	C32—C33—H33A	119.6
C12—C11—P1	117.23 (13)	C33—C34—C35	119.90 (19)
C13—C12—C11	120.77 (19)	C33—C34—H34A	120.0
C13—C12—H12A	119.6	C35—C34—H34A	120.0
C11—C12—H12A	119.6	C36—C35—C34	119.92 (19)
C14—C13—C12	120.1 (2)	C36—C35—H35A	120.0
C14—C13—H13A	119.9	C34—C35—H35A	120.0
C12—C13—H13A	119.9	C35—C36—C31	120.85 (18)
C13—C14—C15	119.8 (2)	C35—C36—H36A	119.6
C13—C14—H14A	120.1	C31—C36—H36A	119.6
C2—N1—N2—C3	−85.2 (2)	O5—P1—C21—C22	−58.38 (15)
C1—O1—C2—O2	−3.3 (3)	C31—P1—C21—C22	64.74 (15)
C1—O1—C2—N1	178.43 (16)	C11—P1—C21—C22	179.61 (13)
N2—N1—C2—O2	8.9 (3)	C26—C21—C22—C23	0.0 (3)
N2—N1—C2—O1	−172.85 (14)	P1—C21—C22—C23	178.68 (14)
C4—O4—C3—O3	2.5 (3)	C21—C22—C23—C24	−0.6 (3)
C4—O4—C3—N2	−174.72 (16)	C22—C23—C24—C25	0.8 (3)
N1—N2—C3—O3	165.73 (17)	C23—C24—C25—C26	−0.6 (3)
N1—N2—C3—O4	−17.0 (2)	C22—C21—C26—C25	0.3 (3)
O5—P1—C11—C16	138.93 (15)	P1—C21—C26—C25	−178.33 (14)
C31—P1—C11—C16	15.04 (17)	C24—C25—C26—C21	0.0 (3)
C21—P1—C11—C16	−97.70 (16)	O5—P1—C31—C36	163.98 (13)
O5—P1—C11—C12	−41.92 (15)	C21—P1—C31—C36	40.60 (16)
C31—P1—C11—C12	−165.81 (13)	C11—P1—C31—C36	−73.19 (15)
C21—P1—C11—C12	81.45 (14)	O5—P1—C31—C32	−16.60 (16)
C16—C11—C12—C13	1.5 (3)	C21—P1—C31—C32	−139.98 (14)
P1—C11—C12—C13	−177.73 (15)	C11—P1—C31—C32	106.23 (15)
C11—C12—C13—C14	−0.4 (3)	C36—C31—C32—C33	0.7 (3)
C12—C13—C14—C15	−1.2 (3)	P1—C31—C32—C33	−178.72 (14)
C13—C14—C15—C16	1.7 (3)	C31—C32—C33—C34	0.5 (3)
C14—C15—C16—C11	−0.7 (3)	C32—C33—C34—C35	−1.2 (3)
C12—C11—C16—C15	−0.9 (3)	C33—C34—C35—C36	0.7 (3)
P1—C11—C16—C15	178.22 (16)	C34—C35—C36—C31	0.5 (3)
O5—P1—C21—C26	120.24 (14)	C32—C31—C36—C35	−1.2 (3)
C31—P1—C21—C26	−116.65 (14)	P1—C31—C36—C35	178.21 (13)
C11—P1—C21—C26	−1.77 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5i	0.85 (2)	2.05 (2)	2.899 (2)	174.2 (19)
N2—H2···O5	0.83 (2)	2.05 (2)	2.833 (2)	155.9 (17)
C13—H13A···O2ii	0.92	2.53	3.310 (3)	143
C35—H35A···O3iii	0.98	2.54	3.270 (3)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O5i	0.85 (2)	2.05 (2)	2.899 (2)	174.2 (19)
N2—H2⋯O5	0.83 (2)	2.05 (2)	2.833 (2)	155.9 (17)
C13—H13A⋯O2ii	0.92	2.53	3.310 (3)	143
C35—H35A⋯O3iii	0.98	2.54	3.270 (3)	131

Symmetry codes: (i) ; (ii) ; (iii) .