Methyl 2-(2-methoxy­carbonyl­acetamido)-3-methyl­butyrate

In the title compound, C₁₀H₁₇NO₅, an intra­molecular C—H...O inter­action generates an S(5) ring motif, whereas inter­molecular N—H—O and C—H...O inter­actions form an R¹₂(6) ring, linking the mol­ecules into a tape along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 230 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.048
• wR factor = 0.147
• Data-to-parameter ratio = 9.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) .         20 Ang.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.04 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.88 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C8
PLAT301_ALERT_3_C Main Residue  Disorder .........................      16.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         12

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           27.49
           From the CIF: _reflns_number_total               1700
           Count of symmetry unique reflns         1699
           Completeness (_total/calc)            100.06%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         1
           Fraction of Friedel pairs measured     0.001
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 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
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Methyl 2-(2-methoxycarbonylacetamido)-3-methylbutyrate

Crystal data

C10H17NO5	F(000) = 496
Mr = 231.25	Dx = 1.198 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4678 reflections
a = 9.2644 (2) Å	θ = 2.5–27.5°
b = 10.7251 (2) Å	µ = 0.10 mm^−1
c = 12.9015 (2) Å	T = 230 K
V = 1281.91 (4) Å^3	Block, colourless
Z = 4	0.33 × 0.26 × 0.21 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	1700 independent reflections
Radiation source: fine-focus sealed tube	1267 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 8.33 pixels mm^-1	θmax = 27.5°, θmin = 2.5°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→13
Tmin = 0.969, Tmax = 0.981	l = −14→16
15828 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.147	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0816P)^2 + 0.1264P] where P = (Fo^2 + 2Fc^2)/3
1700 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.23 e Å^−3
4 restraints	Δρmin = −0.17 e Å^−3

Special details

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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)
O1	0.3684 (3)	0.9866 (2)	0.68851 (19)	0.0831 (7)
O2A	0.4155 (8)	0.7897 (9)	0.7172 (8)	0.091 (2)	0.60
O2B	0.4889 (13)	0.8036 (15)	0.7093 (13)	0.112 (5)	0.40
O3	0.60074 (18)	0.72204 (18)	0.5057 (2)	0.0829 (7)
O4	0.2188 (3)	0.4447 (2)	0.5103 (2)	0.0973 (9)
O5	0.4255 (3)	0.3436 (2)	0.4919 (2)	0.0902 (7)
N1	0.3743 (2)	0.66343 (19)	0.46789 (17)	0.0529 (5)
H1A	0.2844	0.6830	0.4704	0.064*
C1	0.4114 (4)	0.8755 (3)	0.6573 (3)	0.0728 (8)
C2	0.4136 (3)	0.8672 (2)	0.5426 (2)	0.0556 (6)
H2A	0.4735	0.9337	0.5153	0.067*
H2B	0.3165	0.8792	0.5164	0.067*
C3	0.4706 (2)	0.7437 (2)	0.5045 (2)	0.0542 (6)
C4	0.4148 (3)	0.5437 (2)	0.4236 (2)	0.0587 (7)
H4A	0.5191	0.5329	0.4330	0.070*
C5	0.3827 (4)	0.5419 (3)	0.3065 (3)	0.1030 (14)
H5A	0.2851	0.5695	0.2969	0.124*	0.60
H5B	0.4394	0.4743	0.2796	0.124*	0.40
C6A	0.3974 (11)	0.4248 (5)	0.2550 (5)	0.120 (3)	0.60
H6AA	0.3385	0.3637	0.2892	0.180*	0.60
H6AB	0.4965	0.3989	0.2571	0.180*	0.60
H6AC	0.3670	0.4331	0.1842	0.180*	0.60
C6B	0.2379 (7)	0.5090 (11)	0.2805 (6)	0.079 (2)	0.40
H6BA	0.2091	0.4375	0.3202	0.118*	0.40
H6BB	0.2323	0.4897	0.2079	0.118*	0.40
H6BC	0.1750	0.5776	0.2958	0.118*	0.40
C7B	0.442 (3)	0.6468 (17)	0.2531 (17)	0.119 (8)	0.40
H7BA	0.4201	0.6405	0.1806	0.179*	0.40
H7BB	0.5446	0.6485	0.2626	0.179*	0.40
H7BC	0.4005	0.7221	0.2804	0.179*	0.40
C7A	0.474 (2)	0.6263 (17)	0.2511 (15)	0.166 (9)	0.60
H7AA	0.5710	0.6184	0.2757	0.248*	0.60
H7AB	0.4407	0.7101	0.2619	0.248*	0.60
H7AC	0.4704	0.6071	0.1785	0.248*	0.60
C8	0.3400 (3)	0.4413 (2)	0.4810 (2)	0.0631 (7)
C9	0.3652 (6)	0.2347 (3)	0.5436 (4)	0.1226 (18)
H9A	0.4386	0.1720	0.5506	0.184*
H9B	0.2867	0.2022	0.5032	0.184*
H9C	0.3307	0.2580	0.6110	0.184*
C10	0.3686 (7)	1.0113 (5)	0.7996 (3)	0.1217 (17)
H10A	0.3236	1.0904	0.8127	0.182*
H10B	0.4662	1.0130	0.8244	0.182*
H10C	0.3161	0.9468	0.8348	0.182*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.1072 (18)	0.0544 (11)	0.0878 (15)	0.0053 (12)	0.0022 (14)	−0.0092 (11)
O2A	0.127 (6)	0.061 (2)	0.085 (3)	0.006 (4)	0.000 (5)	0.011 (2)
O2B	0.148 (11)	0.088 (8)	0.101 (8)	0.044 (9)	−0.047 (9)	−0.005 (6)
O3	0.0350 (9)	0.0636 (12)	0.150 (2)	0.0002 (8)	−0.0076 (11)	−0.0173 (13)
O4	0.0865 (16)	0.0585 (12)	0.147 (2)	−0.0064 (11)	0.0410 (17)	0.0085 (14)
O5	0.1052 (17)	0.0623 (12)	0.1032 (17)	0.0224 (12)	0.0021 (15)	0.0129 (12)
N1	0.0356 (9)	0.0451 (10)	0.0781 (14)	0.0009 (8)	−0.0024 (9)	−0.0047 (10)
C1	0.084 (2)	0.0471 (13)	0.088 (2)	−0.0021 (15)	−0.0104 (18)	−0.0035 (14)
C2	0.0438 (12)	0.0421 (11)	0.0809 (18)	−0.0028 (10)	−0.0051 (12)	0.0025 (12)
C3	0.0380 (11)	0.0460 (11)	0.0786 (16)	−0.0018 (10)	−0.0031 (11)	0.0013 (12)
C4	0.0471 (13)	0.0563 (13)	0.0727 (17)	−0.0016 (12)	0.0026 (12)	−0.0136 (12)
C5	0.116 (3)	0.128 (3)	0.066 (2)	−0.047 (3)	0.012 (2)	−0.019 (2)
C6A	0.193 (9)	0.078 (4)	0.089 (5)	0.011 (5)	0.001 (6)	−0.033 (3)
C6B	0.072 (5)	0.108 (6)	0.056 (4)	−0.025 (5)	−0.011 (3)	0.004 (4)
C7B	0.18 (2)	0.111 (9)	0.067 (11)	−0.055 (12)	−0.010 (11)	0.032 (8)
C7A	0.113 (8)	0.29 (2)	0.092 (9)	−0.097 (12)	0.039 (6)	−0.022 (11)
C8	0.0654 (17)	0.0463 (12)	0.0777 (19)	0.0024 (12)	0.0018 (14)	−0.0100 (13)
C9	0.180 (5)	0.0576 (18)	0.130 (4)	0.017 (3)	0.005 (4)	0.019 (2)
C10	0.173 (5)	0.099 (3)	0.093 (3)	−0.006 (3)	−0.001 (3)	−0.030 (2)

Geometric parameters (Å, º)

O1—C1	1.320 (4)	C5—C7B	1.429 (4)
O1—C10	1.457 (5)	C5—H5A	0.9601
O2A—C1	1.202 (9)	C5—H5B	0.9600
O2B—C1	1.249 (14)	C6A—H6AA	0.9600
O3—C3	1.228 (3)	C6A—H6AB	0.9600
O4—C8	1.185 (4)	C6A—H6AC	0.9600
O5—C8	1.321 (3)	C6B—H6BA	0.9600
O5—C9	1.457 (5)	C6B—H6BB	0.9600
N1—C3	1.327 (3)	C6B—H6BC	0.9600
N1—C4	1.455 (3)	C7B—H7BA	0.9600
N1—H1A	0.8600	C7B—H7BB	0.9600
C1—C2	1.483 (4)	C7B—H7BC	0.9600
C2—C3	1.509 (3)	C7A—H7AA	0.9600
C2—H2A	0.9700	C7A—H7AB	0.9600
C2—H2B	0.9700	C7A—H7AC	0.9600
C4—C8	1.495 (4)	C9—H9A	0.9600
C4—C5	1.541 (5)	C9—H9B	0.9600
C4—H4A	0.9800	C9—H9C	0.9600
C5—C6A	1.426 (4)	C10—H10A	0.9600
C5—C6B	1.427 (4)	C10—H10B	0.9600
C5—C7A	1.428 (4)	C10—H10C	0.9600
C1—O1—C10	117.6 (3)	C7B—C5—H5B	102.2
C8—O5—C9	117.1 (3)	C4—C5—H5B	104.9
C3—N1—C4	122.6 (2)	C5—C6A—H6AA	109.5
C3—N1—H1A	118.7	C5—C6A—H6AB	109.5
C4—N1—H1A	118.7	C5—C6A—H6AC	109.5
O2A—C1—O1	120.4 (6)	C5—C6B—H6BA	109.5
O2B—C1—O1	124.6 (8)	C5—C6B—H6BB	109.5
O2A—C1—C2	126.5 (6)	H6BA—C6B—H6BB	109.5
O2B—C1—C2	119.4 (8)	C5—C6B—H6BC	109.5
O1—C1—C2	111.3 (3)	H6BA—C6B—H6BC	109.5
C1—C2—C3	112.5 (2)	H6BB—C6B—H6BC	109.5
C1—C2—H2A	109.1	C5—C7B—H7BA	109.5
C3—C2—H2A	109.1	C5—C7B—H7BB	109.5
C1—C2—H2B	109.1	C5—C7B—H7BC	109.5
C3—C2—H2B	109.1	C5—C7A—H7AA	109.5
O3—C3—N1	122.8 (2)	C5—C7A—H7AB	109.5
O3—C3—C2	120.4 (2)	H7AA—C7A—H7AB	109.5
N1—C3—C2	116.8 (2)	C5—C7A—H7AC	109.5
N1—C4—C8	109.6 (2)	H7AA—C7A—H7AC	109.5
N1—C4—C5	110.3 (3)	H7AB—C7A—H7AC	109.5
C8—C4—C5	112.8 (2)	O4—C8—O5	124.0 (3)
N1—C4—H4A	108.0	O4—C8—C4	125.1 (3)
C8—C4—H4A	108.0	O5—C8—C4	110.9 (3)
C5—C4—H4A	108.0	O5—C9—H9A	109.5
C6A—C5—C7A	105.6 (10)	O5—C9—H9B	109.5
C6B—C5—C7A	126.4 (10)	H9A—C9—H9B	109.5
C6A—C5—C7B	115.7 (12)	O5—C9—H9C	109.5
C6B—C5—C7B	116.2 (12)	H9A—C9—H9C	109.5
C6A—C5—C4	116.7 (4)	H9B—C9—H9C	109.5
C6B—C5—C4	114.5 (4)	O1—C10—H10A	109.5
C7A—C5—C4	111.6 (9)	O1—C10—H10B	109.5
C7B—C5—C4	112.9 (10)	H10A—C10—H10B	109.5
C6A—C5—H5A	107.6	O1—C10—H10C	109.5
C7A—C5—H5A	107.2	H10A—C10—H10C	109.5
C4—C5—H5A	107.7	H10B—C10—H10C	109.5
C6B—C5—H5B	104.1
C10—O1—C1—O2A	18.1 (8)	C8—C4—C5—C6A	−48.5 (6)
C10—O1—C1—O2B	−21.3 (10)	N1—C4—C5—C6B	−84.9 (6)
C10—O1—C1—C2	−176.5 (4)	C8—C4—C5—C6B	37.9 (6)
O2A—C1—C2—C3	−19.0 (7)	N1—C4—C5—C7A	67.1 (11)
O2B—C1—C2—C3	20.0 (9)	C8—C4—C5—C7A	−170.1 (10)
O1—C1—C2—C3	176.7 (2)	N1—C4—C5—C7B	51.1 (13)
C4—N1—C3—O3	−1.4 (5)	C8—C4—C5—C7B	173.9 (13)
C4—N1—C3—C2	176.7 (2)	C9—O5—C8—O4	−0.2 (5)
C1—C2—C3—O3	−76.9 (4)	C9—O5—C8—C4	−178.1 (3)
C1—C2—C3—N1	104.9 (3)	N1—C4—C8—O4	40.2 (4)
C3—N1—C4—C8	122.9 (3)	C5—C4—C8—O4	−83.0 (4)
C3—N1—C4—C5	−112.4 (3)	N1—C4—C8—O5	−142.0 (2)
N1—C4—C5—C6A	−171.3 (5)	C5—C4—C8—O5	94.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O3	0.98	2.36	2.783 (3)	105
N1—H1A···O3^i	0.86	2.01	2.837 (3)	162
C2—H2B···O3^i	0.97	2.30	3.115 (3)	142
C6B—H6BC···O2B^i	0.96	2.15	3.063 (17)	160

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