2-Meth­yl-2-nitro­prop­yl methane­sulfonate

The title compound, C₅H₁₁NO₅S, has been obtained by reacting 2-meth­yl-2-nitro­propanol with methane­sulfon­yl chloride. The average S=O and S—O bond lengths are 1.414 (3) and 1.570 (3) Å, respectively. The mol­ecules are linked via C—H...O inter­actions, forming a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.027
• wR factor = 0.078
• Data-to-parameter ratio = 8.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT128_ALERT_4_C Non-standard setting of Space group Fdd2    ....    F2dd
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         S1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           25.14
           From the CIF: _reflns_number_total                861
           Count of symmetry unique reflns          861
           Completeness (_total/calc)            100.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   1 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I)

Crystal data

C5H11NO5S	F(000) = 1664
Mr = 197.21	Dx = 1.460 Mg m^−3
Orthorhombic, F2dd	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F -2d 2	Cell parameters from 25 reflections
a = 8.652 (2) Å	θ = 9.7–13.2°
b = 19.808 (9) Å	µ = 0.35 mm^−1
c = 20.934 (4) Å	T = 295 K
V = 3588 (2) Å^3	Prism, colorless
Z = 16	0.50 × 0.40 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	796 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.015
Graphite monochromator	θmax = 25.1°, θmin = 2.8°
ω/2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = 0→23
Tmin = 0.846, Tmax = 0.903	l = −1→24
909 measured reflections	3 standard reflections every 60 min
861 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.027	w = 1/[σ^2(Fo^2) + (0.0418P)^2 + 2.7911P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.078	(Δ/σ)max < 0.001
S = 1.14	Δρmax = 0.21 e Å^−3
861 reflections	Δρmin = −0.20 e Å^−3
103 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.00104 (14)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), no Friedel pair
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.02 (13)

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
S1	0.07082 (10)	0.13583 (5)	0.88337 (4)	0.0448 (2)
O1	0.6413 (5)	0.10412 (15)	0.83829 (16)	0.0852 (11)
O2	0.5448 (4)	0.20143 (13)	0.82495 (12)	0.0720 (9)
O3	0.2515 (3)	0.13907 (12)	0.87691 (10)	0.0457 (6)
O4	0.0155 (3)	0.19975 (14)	0.90375 (17)	0.0754 (8)
O5	0.0205 (4)	0.10882 (17)	0.82471 (14)	0.0723 (9)
N1	0.5684 (4)	0.15205 (13)	0.85729 (14)	0.0480 (7)
C1	0.5008 (4)	0.15054 (14)	0.92512 (15)	0.0393 (7)
C2	0.6012 (4)	0.19701 (18)	0.96538 (18)	0.0595 (10)
H2A	0.5620	0.1983	1.0083	0.089*
H2B	0.5995	0.2416	0.9475	0.089*
H2C	0.7054	0.1804	0.9658	0.089*
C3	0.5016 (5)	0.07832 (16)	0.94879 (18)	0.0541 (9)
H3A	0.4600	0.0767	0.9913	0.081*
H3B	0.6058	0.0616	0.9491	0.081*
H3C	0.4397	0.0509	0.9210	0.081*
C4	0.3400 (4)	0.17925 (13)	0.92200 (14)	0.0388 (7)
H4A	0.2920	0.1777	0.9639	0.047*
H4B	0.3435	0.2259	0.9081	0.047*
C5	0.0429 (5)	0.0765 (2)	0.94370 (19)	0.0653 (11)
H5A	−0.0657	0.0683	0.9490	0.098*
H5B	0.0853	0.0934	0.9830	0.098*
H5C	0.0938	0.0352	0.9324	0.098*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0348 (4)	0.0583 (5)	0.0415 (4)	−0.0022 (4)	0.0012 (4)	−0.0001 (4)
O1	0.104 (3)	0.0704 (18)	0.081 (2)	0.0245 (18)	0.046 (2)	−0.0001 (16)
O2	0.089 (2)	0.0634 (15)	0.0638 (14)	0.0064 (16)	0.0238 (16)	0.0209 (13)
O3	0.0378 (12)	0.0570 (15)	0.0425 (12)	−0.0059 (11)	0.0026 (10)	−0.0092 (10)
O4	0.0541 (15)	0.0653 (16)	0.107 (2)	0.0114 (14)	0.0015 (16)	−0.0075 (17)
O5	0.0540 (15)	0.117 (2)	0.0458 (14)	−0.0163 (16)	−0.0065 (13)	−0.0052 (14)
N1	0.0412 (15)	0.0512 (18)	0.0515 (14)	−0.0068 (17)	0.0072 (17)	−0.0008 (12)
C1	0.0442 (15)	0.0360 (15)	0.0378 (15)	0.0019 (14)	0.0001 (14)	−0.0013 (12)
C2	0.047 (2)	0.067 (2)	0.065 (2)	−0.0060 (18)	−0.0090 (18)	−0.0145 (18)
C3	0.066 (2)	0.0422 (17)	0.055 (2)	0.0132 (18)	0.0048 (18)	0.0050 (15)
C4	0.0414 (17)	0.0345 (13)	0.0405 (15)	−0.0011 (14)	0.0003 (14)	−0.0055 (11)
C5	0.070 (3)	0.069 (2)	0.057 (2)	−0.026 (2)	0.009 (2)	0.0063 (17)

Geometric parameters (Å, º)

S1—O5	1.409 (3)	C2—H2A	0.9599
S1—O4	1.419 (3)	C2—H2B	0.9599
S1—O3	1.570 (3)	C2—H2C	0.9599
S1—C5	1.742 (4)	C3—H3A	0.9599
O1—N1	1.207 (4)	C3—H3B	0.9599
O2—N1	1.207 (4)	C3—H3C	0.9599
O3—C4	1.453 (4)	C4—H4A	0.9700
N1—C1	1.536 (4)	C4—H4B	0.9700
C1—C4	1.504 (5)	C5—H5A	0.9599
C1—C3	1.514 (4)	C5—H5B	0.9599
C1—C2	1.521 (4)	C5—H5C	0.9599
O5—S1—O4	119.8 (2)	H2A—C2—H2C	109.5
O5—S1—O3	104.37 (16)	H2B—C2—H2C	109.5
O4—S1—O3	108.98 (17)	C1—C3—H3A	109.5
O5—S1—C5	109.5 (2)	C1—C3—H3B	109.5
O4—S1—C5	109.7 (2)	H3A—C3—H3B	109.5
O3—S1—C5	103.17 (19)	C1—C3—H3C	109.5
C4—O3—S1	119.4 (2)	H3A—C3—H3C	109.5
O2—N1—O1	122.7 (3)	H3B—C3—H3C	109.5
O2—N1—C1	118.0 (3)	O3—C4—C1	108.0 (2)
O1—N1—C1	119.2 (3)	O3—C4—H4A	110.1
C4—C1—C3	112.1 (3)	C1—C4—H4A	110.1
C4—C1—C2	108.9 (2)	O3—C4—H4B	110.1
C3—C1—C2	112.8 (3)	C1—C4—H4B	110.1
C4—C1—N1	107.8 (3)	H4A—C4—H4B	108.4
C3—C1—N1	108.6 (3)	S1—C5—H5A	109.5
C2—C1—N1	106.4 (3)	S1—C5—H5B	109.5
C1—C2—H2A	109.5	H5A—C5—H5B	109.5
C1—C2—H2B	109.5	S1—C5—H5C	109.5
H2A—C2—H2B	109.5	H5A—C5—H5C	109.5
C1—C2—H2C	109.5	H5B—C5—H5C	109.5
O5—S1—O3—C4	165.1 (2)	O2—N1—C1—C2	−75.2 (4)
O4—S1—O3—C4	36.1 (3)	O1—N1—C1—C2	105.4 (4)
C5—S1—O3—C4	−80.5 (3)	S1—O3—C4—C1	154.8 (2)
O2—N1—C1—C4	41.4 (4)	C3—C1—C4—O3	−61.7 (3)
O1—N1—C1—C4	−138.0 (4)	C2—C1—C4—O3	172.8 (2)
O2—N1—C1—C3	163.1 (4)	N1—C1—C4—O3	57.8 (3)
O1—N1—C1—C3	−16.3 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O5^i	0.97	2.44	3.339 (4)	155
C4—H4B···O1^ii	0.97	2.57	3.499 (4)	160

Symmetry codes: (i) x+1/4, −y+1/4, z+1/4; (ii) x−1/4, y+1/4, −z+7/4.