N-(3-Nitro­phen­yl)-1-oxo-2,6,7-trioxa-1-phosphabicyclo­[2.2.2]octane-4-carboxamide dimethyl­formamide solvate

In the crystal structure of the title compound, C₁₁H₁₁N₂O₇P, the carboxamide mol­ecule and the solvent mol­ecule of crystallization each possess mirror symmetry; for the former, the mirror plane bisects the two-ring OP(OCH₂)₃C cage. The packing is stabilized by an inter­molecular N—H...O hydrogen bond and a number of C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.043
• wR factor = 0.128
• Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         P1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 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, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

N-(3-Nitrophenyl)-1-oxo-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane-4-carboxamide dimethylformamide solvate

Crystal data

C11H11N2O7P·C3H7NO	F(000) = 404
Mr = 387.28	Dx = 1.439 Mg m^−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 1715 reflections
a = 11.052 (2) Å	θ = 3.1–25.0°
b = 6.7210 (15) Å	µ = 0.20 mm^−1
c = 13.204 (3) Å	T = 294 K
β = 114.344 (3)°	Prism, yellow
V = 893.6 (3) Å^3	0.26 × 0.22 × 0.20 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	2006 independent reflections
Radiation source: fine-focus sealed tube	1335 reflections with I > 2σ
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 26.4°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→13
Tmin = 0.951, Tmax = 0.962	k = −6→8
5100 measured reflections	l = −16→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.128	w = 1/[σ^2(Fo^2) + (0.0619P)^2 + 0.2629P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
2006 reflections	Δρmax = 0.23 e Å^−3
157 parameters	Δρmin = −0.26 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.061 (6)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
P1	0.29102 (9)	0.2500	0.64612 (6)	0.0616 (3)
O1	0.1862 (3)	0.2500	0.53511 (19)	0.0904 (9)
O2	0.2420 (2)	0.2500	0.74101 (16)	0.0659 (7)
O3	0.38695 (16)	0.4327 (3)	0.67331 (12)	0.0809 (6)
O5	0.55676 (18)	0.2500	1.04475 (14)	0.0529 (6)
O6	1.1947 (3)	0.2500	1.0623 (3)	0.1047 (11)
O7	1.2990 (2)	0.2500	1.2386 (2)	0.0851 (8)
N1	0.7166 (2)	0.2500	0.97925 (19)	0.0491 (6)
N2	1.1963 (3)	0.2500	1.1541 (3)	0.0665 (8)
C1	0.4937 (2)	0.4348 (3)	0.78379 (15)	0.0490 (5)
H1C	0.4878	0.5540	0.8230	0.059*
H1D	0.5787	0.4355	0.7786	0.059*
C3	0.3466 (3)	0.2500	0.8533 (2)	0.0457 (7)
H3A	0.3384	0.1331	0.8931	0.055*	0.50
H3B	0.3384	0.3669	0.8931	0.055*	0.50
C4	0.4829 (2)	0.2500	0.8475 (2)	0.0377 (6)
C5	0.5893 (3)	0.2500	0.9673 (2)	0.0393 (6)
C6	0.8331 (3)	0.2500	1.0800 (2)	0.0435 (7)
C7	0.8337 (3)	0.2500	1.1853 (2)	0.0510 (7)
H7	0.7539	0.2500	1.1932	0.061*
C8	0.9530 (3)	0.2500	1.2787 (2)	0.0583 (8)
H8	0.9521	0.2500	1.3488	0.070*
C9	1.0719 (3)	0.2500	1.2700 (2)	0.0541 (8)
H9	1.1517	0.2500	1.3329	0.065*
C10	1.0695 (3)	0.2500	1.1656 (3)	0.0505 (7)
C11	0.9534 (3)	0.2500	1.0698 (2)	0.0482 (7)
H11	0.9556	0.2500	1.0002	0.058*
O8	0.7895 (2)	0.2500	0.79608 (18)	0.0744 (7)
N3	0.8057 (3)	0.2500	0.6311 (2)	0.0586 (7)
C12	0.8541 (3)	0.2500	0.7396 (3)	0.0570 (8)
H12	0.9461	0.2500	0.7776	0.068*
C13	0.6638 (4)	0.2500	0.5664 (3)	0.1112 (18)
H13A	0.6439	0.3086	0.4950	0.167*	0.50
H13B	0.6217	0.3257	0.6046	0.167*	0.50
H13C	0.6314	0.1157	0.5568	0.167*	0.50
C14	0.8901 (4)	0.2500	0.5707 (3)	0.0872 (13)
H14A	0.8579	0.1532	0.5121	0.131*	0.50
H14B	0.9794	0.2174	0.6207	0.131*	0.50
H14C	0.8885	0.3795	0.5395	0.131*	0.50
H1	0.734 (3)	0.2500	0.919 (3)	0.065 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0572 (5)	0.0804 (7)	0.0349 (4)	0.000	0.0068 (4)	0.000
O1	0.0737 (16)	0.134 (2)	0.0426 (13)	0.000	0.0024 (12)	0.000
O2	0.0441 (11)	0.1014 (18)	0.0414 (11)	0.000	0.0069 (9)	0.000
O3	0.0761 (11)	0.0922 (13)	0.0500 (9)	−0.0135 (10)	0.0015 (8)	0.0320 (9)
O5	0.0485 (11)	0.0804 (15)	0.0324 (10)	0.000	0.0193 (9)	0.000
O6	0.0674 (17)	0.165 (3)	0.099 (2)	0.000	0.0519 (17)	0.000
O7	0.0409 (13)	0.0899 (19)	0.111 (2)	0.000	0.0173 (14)	0.000
N1	0.0404 (13)	0.0776 (18)	0.0305 (12)	0.000	0.0158 (10)	0.000
N2	0.0512 (17)	0.0638 (18)	0.087 (2)	0.000	0.0314 (17)	0.000
C1	0.0560 (12)	0.0493 (12)	0.0400 (10)	−0.0024 (10)	0.0182 (9)	0.0022 (9)
C3	0.0417 (14)	0.0560 (17)	0.0358 (14)	0.000	0.0123 (12)	0.000
C4	0.0406 (14)	0.0438 (15)	0.0291 (12)	0.000	0.0146 (11)	0.000
C5	0.0461 (15)	0.0411 (15)	0.0316 (13)	0.000	0.0171 (12)	0.000
C6	0.0423 (15)	0.0495 (16)	0.0379 (14)	0.000	0.0155 (12)	0.000
C7	0.0462 (16)	0.070 (2)	0.0358 (14)	0.000	0.0162 (12)	0.000
C8	0.0554 (18)	0.078 (2)	0.0352 (15)	0.000	0.0126 (14)	0.000
C9	0.0457 (16)	0.0601 (19)	0.0429 (16)	0.000	0.0046 (13)	0.000
C10	0.0409 (15)	0.0446 (16)	0.0644 (19)	0.000	0.0203 (14)	0.000
C11	0.0457 (16)	0.0556 (18)	0.0443 (15)	0.000	0.0196 (13)	0.000
O8	0.0830 (16)	0.105 (2)	0.0506 (13)	0.000	0.0425 (13)	0.000
N3	0.0668 (17)	0.0735 (19)	0.0462 (14)	0.000	0.0341 (13)	0.000
C12	0.0613 (19)	0.061 (2)	0.0515 (18)	0.000	0.0259 (16)	0.000
C13	0.076 (3)	0.199 (6)	0.053 (2)	0.000	0.021 (2)	0.000
C14	0.105 (3)	0.107 (3)	0.081 (3)	0.000	0.070 (2)	0.000

Geometric parameters (Å, º)

P1—O1	1.446 (2)	C6—C7	1.388 (4)
P1—O2	1.557 (2)	C6—C11	1.390 (4)
P1—O3	1.5646 (18)	C7—C8	1.385 (4)
P1—O3^i	1.5646 (18)	C7—H7	0.9300
O2—C3	1.457 (3)	C8—C9	1.365 (4)
O3—C1	1.450 (2)	C8—H8	0.9300
O5—C5	1.217 (3)	C9—C10	1.368 (4)
O6—N2	1.204 (4)	C9—H9	0.9300
O7—N2	1.221 (4)	C10—C11	1.381 (4)
N1—C5	1.349 (4)	C11—H11	0.9300
N1—C6	1.420 (3)	O8—C12	1.226 (4)
N1—H1	0.90 (3)	N3—C12	1.307 (4)
N2—C10	1.471 (4)	N3—C13	1.445 (5)
C1—C4	1.532 (2)	N3—C14	1.455 (4)
C1—H1C	0.9700	C12—H12	0.9300
C1—H1D	0.9700	C13—H13A	0.9600
C3—C4	1.540 (4)	C13—H13B	0.9600
C3—H3A	0.9700	C13—H13C	0.9600
C3—H3B	0.9700	C14—H14A	0.9600
C4—C1^i	1.532 (2)	C14—H14B	0.9600
C4—C5	1.533 (3)	C14—H14C	0.9600
O1—P1—O2	114.63 (14)	C7—C6—N1	124.5 (2)
O1—P1—O3	114.62 (8)	C11—C6—N1	116.3 (2)
O2—P1—O3	104.07 (9)	C8—C7—C6	120.1 (3)
O1—P1—O3^i	114.62 (8)	C8—C7—H7	120.0
O2—P1—O3^i	104.07 (9)	C6—C7—H7	120.0
O3—P1—O3^i	103.45 (15)	C9—C8—C7	121.4 (3)
C3—O2—P1	115.21 (17)	C9—C8—H8	119.3
C1—O3—P1	115.58 (13)	C7—C8—H8	119.3
C5—N1—C6	127.5 (2)	C8—C9—C10	117.7 (3)
C5—N1—H1	120 (2)	C8—C9—H9	121.1
C6—N1—H1	113 (2)	C10—C9—H9	121.1
O6—N2—O7	122.8 (3)	C9—C10—C11	123.2 (3)
O6—N2—C10	119.0 (3)	C9—C10—N2	118.8 (3)
O7—N2—C10	118.2 (3)	C11—C10—N2	118.1 (3)
O3—C1—C4	109.25 (17)	C10—C11—C6	118.4 (3)
O3—C1—H1C	109.8	C10—C11—H11	120.8
C4—C1—H1C	109.8	C6—C11—H11	120.8
O3—C1—H1D	109.8	C12—N3—C13	120.1 (3)
C4—C1—H1D	109.8	C12—N3—C14	122.4 (3)
H1C—C1—H1D	108.3	C13—N3—C14	117.5 (3)
O2—C3—C4	109.3 (2)	O8—C12—N3	126.1 (3)
O2—C3—H3A	109.8	O8—C12—H12	116.9
C4—C3—H3A	109.8	N3—C12—H12	116.9
O2—C3—H3B	109.8	N3—C13—H13A	109.5
C4—C3—H3B	109.8	N3—C13—H13B	109.5
H3A—C3—H3B	108.3	H13A—C13—H13B	109.5
C1^i—C4—C1	108.3 (2)	N3—C13—H13C	109.5
C1^i—C4—C5	111.47 (14)	H13A—C13—H13C	109.5
C1—C4—C5	111.47 (14)	H13B—C13—H13C	109.5
C1^i—C4—C3	109.06 (15)	N3—C14—H14A	109.5
C1—C4—C3	109.06 (14)	N3—C14—H14B	109.5
C5—C4—C3	107.4 (2)	H14A—C14—H14B	109.5
O5—C5—N1	123.8 (2)	N3—C14—H14C	109.5
O5—C5—C4	120.0 (2)	H14A—C14—H14C	109.5
N1—C5—C4	116.1 (2)	H14B—C14—H14C	109.5
C7—C6—C11	119.2 (3)
O1—P1—O2—C3	180.0	C1—C4—C5—N1	−60.60 (15)
O3—P1—O2—C3	−54.03 (7)	C3—C4—C5—N1	180.000 (1)
O3^i—P1—O2—C3	54.03 (7)	C5—N1—C6—C7	0.000 (2)
O1—P1—O3—C1	−179.38 (17)	C5—N1—C6—C11	180.000 (1)
O2—P1—O3—C1	54.65 (18)	C11—C6—C7—C8	0.000 (2)
O3^i—P1—O3—C1	−53.9 (2)	N1—C6—C7—C8	180.000 (2)
P1—O3—C1—C4	−0.4 (2)	C6—C7—C8—C9	0.000 (2)
P1—O2—C3—C4	0.0	C7—C8—C9—C10	0.000 (2)
O3—C1—C4—C1^i	59.9 (3)	C8—C9—C10—C11	0.000 (3)
O3—C1—C4—C5	−177.05 (17)	C8—C9—C10—N2	180.000 (2)
O3—C1—C4—C3	−58.7 (2)	O6—N2—C10—C9	180.000 (2)
O2—C3—C4—C1^i	−59.07 (14)	O7—N2—C10—C9	0.000 (3)
O2—C3—C4—C1	59.07 (14)	O6—N2—C10—C11	0.000 (3)
O2—C3—C4—C5	180.000 (1)	O7—N2—C10—C11	180.000 (2)
C6—N1—C5—O5	0.000 (1)	C9—C10—C11—C6	0.000 (2)
C6—N1—C5—C4	180.000 (1)	N2—C10—C11—C6	180.000 (2)
C1^i—C4—C5—O5	−119.40 (15)	C7—C6—C11—C10	0.000 (2)
C1—C4—C5—O5	119.40 (15)	N1—C6—C11—C10	180.000 (2)
C3—C4—C5—O5	0.000 (1)	C13—N3—C12—O8	0.000 (2)
C1^i—C4—C5—N1	60.60 (15)	C14—N3—C12—O8	180.000 (1)

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O8	0.90 (3)	1.95 (3)	2.847 (3)	175 (3)
C1—H1C···O5^ii	0.97	2.40	3.311 (3)	157
C1—H1D···O8	0.97	2.57	3.439 (3)	149
C1—H1D···O7^iii	0.97	2.57	3.222 (3)	125
C7—H7···O5	0.93	2.25	2.851 (3)	122
C9—H9···O1^iv	0.93	2.54	3.194 (4)	128
C11—H11···O8	0.93	2.56	3.309 (4)	138

Symmetry codes: (ii) −x+1, y+1/2, −z+2; (iii) −x+2, y+1/2, −z+2; (iv) x+1, y, z+1.