tert-Butyl­amido­dichloro­phosphine oxide

The monomeric units in the title compound, C₄H₁₀Cl₂NOP, are linked together by N—H...O hydrogen bonds to give parallel linear strands along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.059
• wR factor = 0.165
• Data-to-parameter ratio = 23.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         P1
PLAT318_ALERT_2_C Check Hybridisation of  N1     in Main Residue .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

   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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

tert-Butylamidodichlorophosphine oxide

Crystal data

C4H10Cl2NOP	F(000) = 392
Mr = 190.00	Dx = 1.450 Mg m^−3
Monoclinic, P21/n	Melting point = 379–381 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.256 (3) Å	Cell parameters from 6208 reflections
b = 10.219 (5) Å	θ = 3.3–27.5°
c = 11.053 (5) Å	µ = 0.86 mm^−1
β = 111.090 (2)°	T = 173 K
V = 870.1 (7) Å^3	Prism, colorless
Z = 4	0.21 × 0.08 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer	1970 independent reflections
Radiation source: fine-focus sealed tube	1538 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω and φ scans	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −10→10
Tmin = 0.840, Tmax = 0.950	k = −13→11
6208 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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.165	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.06P)^2 + 2.44P] where P = (Fo^2 + 2Fc^2)/3
1970 reflections	(Δ/σ)max < 0.001
85 parameters	Δρmax = 0.75 e Å^−3
0 restraints	Δρmin = −0.46 e Å^−3

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

	x	y	z	Uiso*/Ueq
P1	0.79303 (12)	0.11098 (9)	0.24634 (11)	0.0325 (3)
Cl1	0.87620 (15)	0.16877 (14)	0.10558 (11)	0.0548 (4)
Cl2	1.00214 (16)	0.15702 (15)	0.40162 (12)	0.0619 (4)
O1	0.7555 (4)	−0.0283 (3)	0.2389 (4)	0.0617 (10)
N1	0.6393 (4)	0.2076 (3)	0.2418 (4)	0.0395 (8)
H1	0.6591	0.2917	0.2371	0.047*
C1	0.4658 (5)	0.1715 (4)	0.2446 (4)	0.0316 (8)
C2	0.4873 (7)	0.0984 (5)	0.3691 (5)	0.0524 (12)
H2A	0.5478	0.0156	0.3707	0.079*
H2B	0.3728	0.0807	0.3733	0.079*
H2C	0.5553	0.1519	0.4437	0.079*
C3	0.3741 (5)	0.3015 (4)	0.2429 (5)	0.0433 (10)
H3A	0.4416	0.3533	0.3190	0.065*
H3B	0.2581	0.2850	0.2447	0.065*
H3C	0.3638	0.3498	0.1638	0.065*
C4	0.3651 (6)	0.0915 (5)	0.1255 (5)	0.0501 (11)
H4A	0.4208	0.0061	0.1302	0.075*
H4B	0.3636	0.1378	0.0474	0.075*
H4C	0.2457	0.0791	0.1220	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0283 (5)	0.0226 (5)	0.0489 (6)	0.0019 (4)	0.0165 (4)	−0.0005 (4)
Cl1	0.0484 (6)	0.0756 (9)	0.0479 (6)	0.0141 (6)	0.0267 (5)	0.0056 (6)
Cl2	0.0442 (6)	0.0844 (10)	0.0442 (6)	0.0185 (6)	0.0003 (5)	−0.0092 (6)
O1	0.0475 (18)	0.0218 (14)	0.124 (3)	0.0036 (13)	0.040 (2)	−0.0027 (17)
N1	0.0316 (16)	0.0172 (14)	0.078 (3)	0.0028 (13)	0.0296 (17)	0.0028 (15)
C1	0.0278 (17)	0.0288 (19)	0.042 (2)	−0.0042 (14)	0.0170 (16)	0.0002 (16)
C2	0.063 (3)	0.053 (3)	0.051 (3)	0.010 (2)	0.033 (2)	0.016 (2)
C3	0.035 (2)	0.035 (2)	0.066 (3)	0.0032 (18)	0.026 (2)	0.001 (2)
C4	0.042 (2)	0.054 (3)	0.051 (3)	−0.010 (2)	0.013 (2)	−0.016 (2)

Geometric parameters (Å, º)

P1—O1	1.453 (3)	C2—H2A	0.9800
P1—N1	1.595 (3)	C2—H2B	0.9800
P1—Cl1	2.0025 (17)	C2—H2C	0.9800
P1—Cl2	2.0038 (17)	C3—H3A	0.9800
N1—C1	1.490 (5)	C3—H3B	0.9800
N1—H1	0.8800	C3—H3C	0.9800
C1—C2	1.519 (6)	C4—H4A	0.9800
C1—C4	1.518 (6)	C4—H4B	0.9800
C1—C3	1.526 (6)	C4—H4C	0.9800
O1—P1—N1	116.98 (18)	H2A—C2—H2B	109.5
O1—P1—Cl1	111.76 (18)	C1—C2—H2C	109.5
N1—P1—Cl1	106.53 (15)	H2A—C2—H2C	109.5
O1—P1—Cl2	112.28 (18)	H2B—C2—H2C	109.5
N1—P1—Cl2	108.20 (15)	C1—C3—H3A	109.5
Cl1—P1—Cl2	99.53 (8)	C1—C3—H3B	109.5
C1—N1—P1	127.3 (3)	H3A—C3—H3B	109.5
C1—N1—H1	116.3	C1—C3—H3C	109.5
P1—N1—H1	116.3	H3A—C3—H3C	109.5
N1—C1—C2	109.9 (4)	H3B—C3—H3C	109.5
N1—C1—C4	110.2 (3)	C1—C4—H4A	109.5
C2—C1—C4	111.7 (4)	C1—C4—H4B	109.5
N1—C1—C3	105.1 (3)	H4A—C4—H4B	109.5
C2—C1—C3	109.6 (4)	C1—C4—H4C	109.5
C4—C1—C3	110.1 (4)	H4A—C4—H4C	109.5
C1—C2—H2A	109.5	H4B—C4—H4C	109.5
C1—C2—H2B	109.5
O1—P1—N1—C1	7.0 (5)	P1—N1—C1—C2	60.2 (5)
Cl1—P1—N1—C1	132.8 (3)	P1—N1—C1—C4	−63.4 (5)
Cl2—P1—N1—C1	−121.0 (4)	P1—N1—C1—C3	178.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.88	1.95	2.820 (4)	168

Symmetry code: (i) −x+3/2, y+1/2, −z+1/2.