tert-Butyl (S)-N-[(S)-1-(oxiranyl)ethyl]carbamate

The investigation of the title compound, C₉H₁₇NO₃, which has two independent but virtually identical mol­ecules in the asymmetric unit, allowed the determination of the relative configurations of the chiral atoms as S.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.055
• wR factor = 0.128
• Data-to-parameter ratio = 10.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C2A
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C2B
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C3A
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C6A
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C3B
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C6B
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C1A    -   C2A    ...       1.43 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.50
           From the CIF: _reflns_number_total               2685
           Count of symmetry unique reflns         2690
           Completeness (_total/calc)             99.81%
           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         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 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
   7 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: XSCANS (Siemens, 1993); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

tert-Butyl (S)—N-[(S)-(1-oxiranylethyl)]carbamate

Crystal data

C9H17NO3	F(000) = 408
Mr = 187.24	Dx = 1.118 Mg m^−3
Monoclinic, P21	Melting point = 321–323 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 9.741 (2) Å	Cell parameters from 37 reflections
b = 10.882 (2) Å	θ = 5.0–12.5°
c = 10.492 (1) Å	µ = 0.08 mm^−1
β = 90.04 (1)°	T = 294 K
V = 1112.2 (3) Å^3	Block, colourless
Z = 4	0.50 × 0.40 × 0.34 mm

Data collection

Siemens P4/PC diffractometer	1465 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 27.5°, θmin = 2.1°
ω–2θ scans	h = 0→12
Absorption correction: ψ scan (XPREP in SHELXTL; Sheldrick, 2000)	k = 0→14
Tmin = 0.955, Tmax = 0.971	l = −13→13
2835 measured reflections	3 standard reflections every 97 reflections
2685 independent reflections	intensity decay: 2.6%

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)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.128	w = 1/[σ^2(Fo^2) + (0.0453P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
2685 reflections	Δρmax = 0.13 e Å^−3
250 parameters	Δρmin = −0.12 e Å^−3
2 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: 0.063 (7)

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
O1A	0.6148 (4)	0.2702 (4)	0.5501 (3)	0.0853 (12)
O2A	0.5251 (3)	0.3716 (4)	0.9627 (3)	0.0730 (11)
O3A	0.7383 (3)	0.3787 (4)	1.0516 (2)	0.0643 (10)
N1A	0.7139 (3)	0.4277 (4)	0.8503 (3)	0.0592 (11)
H1A	0.798 (4)	0.422 (5)	0.852 (4)	0.071*
C1A	0.6839 (6)	0.3023 (5)	0.6646 (5)	0.0686 (15)
H1	0.7809	0.2787	0.6684	0.082*
C2A	0.5888 (7)	0.2026 (6)	0.6641 (6)	0.098 (2)
H2	0.6253	0.1199	0.6701	0.118*
H3	0.5011	0.2149	0.7061	0.118*
C3A	0.6501 (4)	0.4234 (4)	0.7239 (4)	0.0518 (11)
H4	0.5503	0.4284	0.7346	0.062*
C4A	0.6962 (7)	0.5310 (6)	0.6437 (5)	0.0854 (18)
H5	0.6714	0.6064	0.6854	0.128*
H6	0.6525	0.5272	0.5618	0.128*
H7	0.7940	0.5279	0.6330	0.128*
C5A	0.6474 (4)	0.3904 (5)	0.9546 (3)	0.0532 (10)
C6A	0.6916 (4)	0.3442 (5)	1.1810 (4)	0.0643 (15)
C7A	0.8264 (5)	0.3408 (7)	1.2546 (5)	0.095 (2)
H8	0.8837	0.2768	1.2210	0.142*
H9	0.8081	0.3250	1.3430	0.142*
H10	0.8723	0.4185	1.2461	0.142*
C8A	0.6263 (6)	0.2187 (6)	1.1808 (5)	0.0904 (19)
H11	0.5431	0.2210	1.1317	0.136*
H12	0.6056	0.1948	1.2667	0.136*
H13	0.6886	0.1604	1.1438	0.136*
C9A	0.5995 (6)	0.4414 (7)	1.2328 (5)	0.099 (2)
H14	0.6452	0.5195	1.2290	0.149*
H15	0.5771	0.4227	1.3198	0.149*
H16	0.5168	0.4447	1.1831	0.149*
O1B	0.1054 (4)	0.5409 (4)	1.2094 (3)	0.0916 (13)
O2B	0.0220 (2)	0.4155 (4)	0.7993 (2)	0.0644 (10)
O3B	0.2307 (2)	0.3956 (4)	0.7046 (2)	0.0567 (8)
N1B	0.2154 (3)	0.3837 (5)	0.9125 (3)	0.0596 (11)
H1B	0.298 (4)	0.371 (5)	0.906 (4)	0.071*
C1B	0.1770 (6)	0.5146 (6)	1.0956 (4)	0.0712 (16)
H17	0.2720	0.5439	1.0924	0.085*
C2B	0.0737 (7)	0.6088 (7)	1.0954 (6)	0.104 (2)
H18	−0.0126	0.5915	1.0529	0.124*
H19	0.1039	0.6937	1.0906	0.124*
C3B	0.1526 (4)	0.3901 (5)	1.0387 (3)	0.0545 (11)
H20	0.0534	0.3786	1.0289	0.065*
C4B	0.2077 (6)	0.2867 (6)	1.1228 (5)	0.0787 (17)
H21	0.1892	0.2089	1.0832	0.118*
H22	0.1637	0.2898	1.2045	0.118*
H23	0.3050	0.2964	1.1335	0.118*
C5B	0.1450 (3)	0.3994 (5)	0.8047 (3)	0.0470 (9)
C6B	0.1790 (4)	0.4020 (5)	0.5731 (3)	0.0533 (11)
C7B	0.3097 (4)	0.3950 (7)	0.4951 (4)	0.0791 (16)
H24	0.3683	0.4629	0.5166	0.119*
H25	0.2873	0.3986	0.4060	0.119*
H26	0.3563	0.3193	0.5131	0.119*
C8B	0.1121 (7)	0.5229 (7)	0.5502 (5)	0.091 (2)
H27	0.0321	0.5300	0.6031	0.136*
H28	0.0856	0.5289	0.4623	0.136*
H29	0.1753	0.5877	0.5704	0.136*
C9B	0.0874 (7)	0.2946 (7)	0.5469 (6)	0.099 (2)
H30	0.1305	0.2207	0.5769	0.148*
H31	0.0715	0.2882	0.4568	0.148*
H32	0.0015	0.3059	0.5901	0.148*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.099 (3)	0.103 (3)	0.0533 (19)	0.015 (2)	−0.0048 (19)	−0.015 (2)
O2A	0.0404 (15)	0.123 (3)	0.0554 (16)	0.003 (2)	0.0024 (11)	0.014 (2)
O3A	0.0416 (13)	0.108 (3)	0.0428 (14)	−0.001 (2)	0.0017 (10)	0.0104 (19)
N1A	0.0415 (17)	0.090 (3)	0.0465 (17)	−0.003 (2)	−0.0043 (14)	0.007 (2)
C1A	0.063 (3)	0.089 (4)	0.054 (3)	0.019 (3)	−0.003 (2)	−0.001 (3)
C2A	0.137 (6)	0.070 (4)	0.087 (4)	−0.007 (4)	0.006 (4)	−0.009 (3)
C3A	0.044 (2)	0.065 (3)	0.047 (2)	0.002 (2)	−0.0058 (16)	0.004 (2)
C4A	0.093 (4)	0.098 (5)	0.065 (3)	−0.014 (4)	−0.008 (3)	0.022 (3)
C5A	0.0410 (18)	0.070 (3)	0.048 (2)	0.004 (3)	0.0019 (15)	0.006 (2)
C6A	0.052 (2)	0.103 (4)	0.038 (2)	0.006 (3)	0.0020 (18)	0.011 (2)
C7A	0.065 (3)	0.164 (7)	0.055 (3)	−0.006 (4)	−0.009 (2)	0.026 (3)
C8A	0.090 (4)	0.101 (5)	0.080 (4)	−0.009 (4)	0.001 (3)	0.026 (4)
C9A	0.102 (4)	0.134 (7)	0.062 (3)	0.031 (4)	0.013 (3)	−0.016 (4)
O1B	0.110 (3)	0.111 (3)	0.0539 (19)	−0.017 (3)	0.0077 (19)	−0.014 (2)
O2B	0.0367 (13)	0.110 (3)	0.0468 (14)	0.0065 (19)	−0.0015 (10)	0.0062 (18)
O3B	0.0398 (12)	0.093 (2)	0.0370 (12)	−0.0026 (19)	−0.0017 (9)	0.0046 (18)
N1B	0.0388 (15)	0.100 (3)	0.0402 (16)	0.002 (2)	−0.0021 (13)	0.007 (2)
C1B	0.072 (3)	0.094 (4)	0.048 (3)	−0.028 (3)	0.003 (2)	0.003 (3)
C2B	0.131 (6)	0.079 (5)	0.100 (5)	−0.004 (5)	−0.007 (4)	−0.009 (4)
C3B	0.0465 (19)	0.078 (3)	0.0389 (18)	−0.001 (3)	0.0007 (14)	0.011 (3)
C4B	0.075 (4)	0.095 (4)	0.066 (3)	−0.002 (3)	−0.003 (3)	0.021 (3)
C5B	0.0410 (18)	0.059 (3)	0.0407 (18)	−0.007 (2)	−0.0037 (14)	−0.002 (2)
C6B	0.0479 (18)	0.076 (3)	0.0361 (17)	−0.005 (3)	−0.0037 (14)	−0.002 (2)
C7B	0.064 (2)	0.128 (5)	0.045 (2)	0.006 (4)	0.0032 (18)	−0.003 (3)
C8B	0.111 (5)	0.110 (5)	0.051 (3)	0.032 (4)	0.009 (3)	0.009 (3)
C9B	0.093 (5)	0.119 (6)	0.083 (4)	−0.043 (4)	0.000 (4)	−0.033 (4)

Geometric parameters (Å, º)

O1A—C1A	1.420 (6)	O1B—C1B	1.413 (6)
O1A—C2A	1.427 (7)	O1B—C2B	1.439 (8)
O2A—C5A	1.211 (4)	O2B—C5B	1.212 (4)
O3A—C5A	1.355 (4)	O3B—C5B	1.342 (4)
O3A—C6A	1.481 (5)	O3B—C6B	1.470 (4)
N1A—C3A	1.464 (5)	N1B—C3B	1.460 (4)
N1A—C5A	1.336 (5)	N1B—C5B	1.334 (5)
N1A—H1A	0.82 (3)	N1B—H1B	0.81 (3)
C1A—C2A	1.427 (8)	C1B—C2B	1.436 (9)
C1A—C3A	1.495 (7)	C1B—C3B	1.499 (8)
C1A—H1	0.9800	C1B—H17	0.9800
C2A—H2	0.9700	C2B—H18	0.9700
C2A—H3	0.9700	C2B—H19	0.9700
C3A—C4A	1.511 (7)	C3B—C4B	1.527 (7)
C3A—H4	0.9800	C3B—H20	0.9800
C4A—H5	0.9600	C4B—H21	0.9600
C4A—H6	0.9600	C4B—H22	0.9600
C4A—H7	0.9600	C4B—H23	0.9600
C6A—C7A	1.523 (6)	C6B—C7B	1.516 (5)
C6A—C8A	1.507 (8)	C6B—C8B	1.488 (8)
C6A—C9A	1.489 (7)	C6B—C9B	1.496 (8)
C7A—H8	0.9600	C7B—H24	0.9600
C7A—H9	0.9600	C7B—H25	0.9600
C7A—H10	0.9600	C7B—H26	0.9600
C8A—H11	0.9600	C8B—H27	0.9600
C8A—H12	0.9600	C8B—H28	0.9600
C8A—H13	0.9600	C8B—H29	0.9600
C9A—H14	0.9600	C9B—H30	0.9600
C9A—H15	0.9600	C9B—H31	0.9600
C9A—H16	0.9600	C9B—H32	0.9600
C1A—O1A—C2A	60.2 (4)	C1B—O1B—C2B	60.5 (4)
C5A—O3A—C6A	120.8 (3)	C5B—O3B—C6B	121.3 (3)
C3A—N1A—C5A	121.8 (4)	C3B—N1B—C5B	123.2 (3)
C3A—N1A—H1A	116 (3)	C3B—N1B—H1B	119 (3)
C5A—N1A—H1A	116 (3)	C5B—N1B—H1B	117 (3)
O1A—C1A—C2A	60.2 (4)	O1B—C1B—C2B	60.7 (4)
O1A—C1A—C3A	117.7 (4)	O1B—C1B—C3B	116.2 (4)
C2A—C1A—C3A	121.9 (5)	C2B—C1B—C3B	122.3 (5)
O1A—C1A—H1	115.3	O1B—C1B—H17	115.4
C2A—C1A—H1	115.3	C2B—C1B—H17	115.4
C3A—C1A—H1	115.3	C3B—C1B—H17	115.4
O1A—C2A—C1A	59.7 (4)	C1B—C2B—O1B	58.8 (4)
O1A—C2A—H2	117.8	C1B—C2B—H18	117.9
C1A—C2A—H2	117.8	O1B—C2B—H18	117.9
O1A—C2A—H3	117.8	C1B—C2B—H19	117.9
C1A—C2A—H3	117.8	O1B—C2B—H19	117.9
H2—C2A—H3	114.9	H18—C2B—H19	115.0
N1A—C3A—C1A	108.1 (4)	N1B—C3B—C1B	109.7 (4)
N1A—C3A—C4A	110.7 (4)	N1B—C3B—C4B	110.0 (4)
C1A—C3A—C4A	112.7 (4)	C1B—C3B—C4B	112.3 (4)
N1A—C3A—H4	108.4	N1B—C3B—H20	108.2
C1A—C3A—H4	108.4	C1B—C3B—H20	108.2
C4A—C3A—H4	108.4	C4B—C3B—H20	108.2
C3A—C4A—H5	109.5	C3B—C4B—H21	109.5
C3A—C4A—H6	109.5	C3B—C4B—H22	109.5
H5—C4A—H6	109.5	H21—C4B—H22	109.5
C3A—C4A—H7	109.5	C3B—C4B—H23	109.5
H5—C4A—H7	109.5	H21—C4B—H23	109.5
H6—C4A—H7	109.5	H22—C4B—H23	109.5
O2A—C5A—N1A	125.9 (3)	O2B—C5B—N1B	124.4 (3)
O2A—C5A—O3A	125.0 (3)	O2B—C5B—O3B	125.7 (3)
N1A—C5A—O3A	109.1 (3)	N1B—C5B—O3B	109.9 (3)
O3A—C6A—C9A	109.9 (4)	O3B—C6B—C8B	110.0 (4)
O3A—C6A—C8A	111.0 (4)	O3B—C6B—C9B	109.8 (4)
C9A—C6A—C8A	113.0 (5)	C8B—C6B—C9B	113.6 (4)
O3A—C6A—C7A	101.8 (3)	O3B—C6B—C7B	102.6 (3)
C9A—C6A—C7A	110.6 (5)	C8B—C6B—C7B	109.0 (5)
C8A—C6A—C7A	110.0 (5)	C9B—C6B—C7B	111.3 (5)
C6A—C7A—H8	109.5	C6B—C7B—H24	109.5
C6A—C7A—H9	109.5	C6B—C7B—H25	109.5
H8—C7A—H9	109.5	H24—C7B—H25	109.5
C6A—C7A—H10	109.5	C6B—C7B—H26	109.5
H8—C7A—H10	109.5	H24—C7B—H26	109.5
H9—C7A—H10	109.5	H25—C7B—H26	109.5
C6A—C8A—H11	109.5	C6B—C8B—H27	109.5
C6A—C8A—H12	109.5	C6B—C8B—H28	109.5
H11—C8A—H12	109.5	H27—C8B—H28	109.5
C6A—C8A—H13	109.5	C6B—C8B—H29	109.5
H11—C8A—H13	109.5	H27—C8B—H29	109.5
H12—C8A—H13	109.5	H28—C8B—H29	109.5
C6A—C9A—H14	109.5	C6B—C9B—H30	109.5
C6A—C9A—H15	109.5	C6B—C9B—H31	109.5
H14—C9A—H15	109.5	H30—C9B—H31	109.5
C6A—C9A—H16	109.5	C6B—C9B—H32	109.5
H14—C9A—H16	109.5	H30—C9B—H32	109.5
H15—C9A—H16	109.5	H31—C9B—H32	109.5
C2A—O1A—C1A—C3A	−112.7 (6)	C2B—O1B—C1B—C3B	−114.0 (6)
C3A—C1A—C2A—O1A	105.9 (5)	C3B—C1B—C2B—O1B	104.2 (5)
C5A—N1A—C3A—C1A	−91.2 (6)	C5B—N1B—C3B—C1B	−98.7 (6)
C5A—N1A—C3A—C4A	144.9 (5)	C5B—N1B—C3B—C4B	137.3 (5)
O1A—C1A—C3A—N1A	170.2 (4)	O1B—C1B—C3B—N1B	171.1 (4)
C2A—C1A—C3A—N1A	99.8 (6)	C2B—C1B—C3B—N1B	100.6 (6)
O1A—C1A—C3A—C4A	−67.1 (6)	O1B—C1B—C3B—C4B	−66.3 (6)
C2A—C1A—C3A—C4A	−137.5 (5)	C2B—C1B—C3B—C4B	−136.7 (6)
C3A—N1A—C5A—O2A	−14.4 (9)	C3B—N1B—C5B—O2B	−3.0 (9)
C3A—N1A—C5A—O3A	166.7 (4)	C3B—N1B—C5B—O3B	176.4 (5)
C6A—O3A—C5A—O2A	−1.9 (9)	C6B—O3B—C5B—O2B	−4.8 (8)
C6A—O3A—C5A—N1A	177.0 (4)	C6B—O3B—C5B—N1B	175.8 (4)
C5A—O3A—C6A—C9A	−63.5 (6)	C5B—O3B—C6B—C8B	64.0 (6)
C5A—O3A—C6A—C8A	62.1 (6)	C5B—O3B—C6B—C9B	−61.7 (6)
C5A—O3A—C6A—C7A	179.2 (5)	C5B—O3B—C6B—C7B	179.9 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1B—H1B···O2A	0.81 (3)	2.29 (4)	3.065 (4)	158 (5)
N1A—H1A···O2B^i	0.82 (3)	2.25 (4)	3.051 (4)	164 (4)

Symmetry code: (i) x+1, y, z.