Isopropyl 2-oxo-3,4-dihydro-1,4-benzoxazine-4-acetate

In the crystal structure of the title compound, C₁₃H₁₅NO₄, adjacent mol­ecules are linked together by C—H...O hydrogen bonding to form one-dimensional supra­molecular chains.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.057
• wR factor = 0.274
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.274
PLAT084_ALERT_2_C High R2 Value ..................................       0.27
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6     ..  O2      ..       2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8B    ..  O1      ..       2.62 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 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
   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: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Isopropyl 2-oxo-3,4-dihydro-1,4-benzoxazine-4-acetate

Crystal data

C13H15NO4	F(000) = 528
Mr = 249.26	Dx = 1.303 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1010 reflections
a = 13.632 (6) Å	θ = 2.6–20.6°
b = 9.587 (4) Å	µ = 0.10 mm^−1
c = 10.240 (5) Å	T = 298 K
β = 108.349 (6)°	Rectangle, colorless
V = 1270.2 (10) Å^3	0.48 × 0.39 × 0.14 mm
Z = 4

Data collection

Bruker CCD area-detector diffractometer	1134 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.052
Graphite monochromator	θmax = 25.0°, θmin = 1.5°
φ and ω scans	h = −13→16
6376 measured reflections	k = −11→9
2234 independent reflections	l = −11→12

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.274	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.116P)^2 + 0.2459P] where P = (Fo^2 + 2Fc^2)/3
2234 reflections	(Δ/σ)max < 0.001
165 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

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
N1	0.3795 (2)	0.4579 (3)	0.4064 (3)	0.0504 (9)
O2	0.5507 (2)	0.5936 (3)	0.2382 (3)	0.0730 (10)
O3	0.17099 (19)	0.2136 (3)	0.3604 (3)	0.0645 (9)
O4	0.1893 (2)	0.3773 (3)	0.2144 (4)	0.0898 (12)
C8	0.4229 (3)	0.4595 (4)	0.2946 (5)	0.0578 (11)
H8A	0.3673	0.4491	0.2086	0.069*
H8B	0.4684	0.3797	0.3041	0.069*
C7	0.4820 (3)	0.5881 (4)	0.2873 (5)	0.0549 (11)
O1	0.4533 (2)	0.7072 (2)	0.3347 (3)	0.0577 (8)
C1	0.3738 (3)	0.7076 (4)	0.3932 (4)	0.0497 (10)
C2	0.3360 (3)	0.5839 (4)	0.4300 (4)	0.0490 (10)
C3	0.2629 (3)	0.5947 (4)	0.4971 (5)	0.0647 (12)
H3	0.2373	0.5142	0.5252	0.078*
C4	0.2274 (4)	0.7233 (5)	0.5229 (5)	0.0769 (14)
H4	0.1784	0.7286	0.5687	0.092*
C5	0.2638 (4)	0.8436 (5)	0.4814 (5)	0.0759 (14)
H5	0.2385	0.9299	0.4972	0.091*
C6	0.3375 (3)	0.8357 (4)	0.4165 (5)	0.0645 (12)
H6	0.3627	0.9166	0.3885	0.077*
C9	0.2224 (3)	0.3115 (4)	0.3186 (4)	0.0545 (10)
C10	0.3292 (3)	0.3288 (4)	0.4217 (4)	0.0538 (11)
H10A	0.3237	0.3249	0.5138	0.065*
H10B	0.3721	0.2513	0.4119	0.065*
C11	0.0660 (3)	0.1809 (4)	0.2702 (5)	0.0643 (12)
H11	0.0339	0.2647	0.2199	0.077*
C12	0.0082 (4)	0.1356 (7)	0.3651 (7)	0.111 (2)
H12A	0.0389	0.0521	0.4123	0.166*
H12B	−0.0626	0.1177	0.3129	0.166*
H12C	0.0111	0.2080	0.4310	0.166*
C13	0.0729 (4)	0.0712 (6)	0.1723 (6)	0.1020 (19)
H13A	0.1116	0.1056	0.1153	0.153*
H13B	0.0046	0.0460	0.1157	0.153*
H13C	0.1069	−0.0092	0.2223	0.153*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0461 (18)	0.0426 (18)	0.066 (2)	−0.0026 (14)	0.0223 (17)	0.0019 (15)
O2	0.074 (2)	0.0632 (19)	0.096 (3)	−0.0003 (15)	0.048 (2)	0.0070 (15)
O3	0.0504 (16)	0.0719 (19)	0.063 (2)	−0.0180 (14)	0.0055 (14)	0.0085 (14)
O4	0.073 (2)	0.088 (2)	0.090 (3)	−0.0127 (17)	0.0000 (19)	0.035 (2)
C8	0.061 (3)	0.046 (2)	0.073 (3)	−0.0014 (18)	0.030 (2)	−0.001 (2)
C7	0.052 (2)	0.052 (2)	0.063 (3)	0.0026 (18)	0.022 (2)	0.006 (2)
O1	0.0565 (17)	0.0433 (16)	0.077 (2)	−0.0018 (12)	0.0272 (15)	0.0030 (13)
C1	0.041 (2)	0.051 (2)	0.057 (3)	0.0022 (17)	0.0142 (18)	0.0001 (18)
C2	0.044 (2)	0.051 (2)	0.050 (2)	0.0017 (17)	0.0118 (18)	−0.0007 (18)
C3	0.056 (3)	0.072 (3)	0.071 (3)	0.000 (2)	0.027 (2)	0.003 (2)
C4	0.065 (3)	0.091 (4)	0.081 (4)	0.010 (3)	0.031 (3)	−0.011 (3)
C5	0.073 (3)	0.072 (3)	0.078 (3)	0.019 (3)	0.018 (3)	−0.012 (3)
C6	0.067 (3)	0.049 (3)	0.072 (3)	0.009 (2)	0.015 (2)	−0.003 (2)
C9	0.052 (2)	0.051 (2)	0.058 (3)	−0.0038 (18)	0.013 (2)	0.004 (2)
C10	0.047 (2)	0.050 (2)	0.061 (3)	−0.0063 (17)	0.0114 (19)	0.0047 (19)
C11	0.051 (2)	0.069 (3)	0.069 (3)	−0.011 (2)	0.012 (2)	0.000 (2)
C12	0.080 (4)	0.156 (5)	0.105 (5)	−0.050 (4)	0.043 (3)	−0.045 (4)
C13	0.090 (4)	0.121 (5)	0.086 (4)	−0.005 (3)	0.015 (3)	−0.040 (3)

Geometric parameters (Å, º)

N1—C2	1.400 (4)	C4—C5	1.375 (6)
N1—C8	1.445 (5)	C4—H4	0.9300
N1—C10	1.447 (4)	C5—C6	1.370 (6)
O2—C7	1.196 (4)	C5—H5	0.9300
O3—C9	1.321 (4)	C6—H6	0.9300
O3—C11	1.472 (5)	C9—C10	1.515 (5)
O4—C9	1.198 (5)	C10—H10A	0.9700
C8—C7	1.487 (5)	C10—H10B	0.9700
C8—H8A	0.9700	C11—C13	1.476 (6)
C8—H8B	0.9700	C11—C12	1.495 (7)
C7—O1	1.346 (4)	C11—H11	0.9800
O1—C1	1.393 (4)	C12—H12A	0.9600
C1—C6	1.373 (5)	C12—H12B	0.9600
C1—C2	1.392 (5)	C12—H12C	0.9600
C2—C3	1.380 (5)	C13—H13A	0.9600
C3—C4	1.380 (5)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C2—N1—C8	115.4 (3)	C5—C6—H6	120.2
C2—N1—C10	118.6 (3)	C1—C6—H6	120.2
C8—N1—C10	114.9 (3)	O4—C9—O3	125.0 (4)
C9—O3—C11	117.3 (3)	O4—C9—C10	125.0 (4)
N1—C8—C7	114.3 (3)	O3—C9—C10	110.1 (3)
N1—C8—H8A	108.7	N1—C10—C9	113.7 (3)
C7—C8—H8A	108.7	N1—C10—H10A	108.8
N1—C8—H8B	108.7	C9—C10—H10A	108.8
C7—C8—H8B	108.7	N1—C10—H10B	108.8
H8A—C8—H8B	107.6	C9—C10—H10B	108.8
O2—C7—O1	118.0 (3)	H10A—C10—H10B	107.7
O2—C7—C8	124.5 (4)	O3—C11—C13	108.7 (4)
O1—C7—C8	117.5 (3)	O3—C11—C12	105.2 (4)
C7—O1—C1	120.7 (3)	C13—C11—C12	113.2 (4)
C6—C1—C2	122.0 (4)	O3—C11—H11	109.9
C6—C1—O1	116.7 (3)	C13—C11—H11	109.9
C2—C1—O1	121.3 (3)	C12—C11—H11	109.9
C3—C2—C1	117.3 (3)	C11—C12—H12A	109.5
C3—C2—N1	124.2 (3)	C11—C12—H12B	109.5
C1—C2—N1	118.4 (3)	H12A—C12—H12B	109.5
C2—C3—C4	120.9 (4)	C11—C12—H12C	109.5
C2—C3—H3	119.5	H12A—C12—H12C	109.5
C4—C3—H3	119.5	H12B—C12—H12C	109.5
C5—C4—C3	120.5 (4)	C11—C13—H13A	109.5
C5—C4—H4	119.8	C11—C13—H13B	109.5
C3—C4—H4	119.8	H13A—C13—H13B	109.5
C6—C5—C4	119.7 (4)	C11—C13—H13C	109.5
C6—C5—H5	120.2	H13A—C13—H13C	109.5
C4—C5—H5	120.2	H13B—C13—H13C	109.5
C5—C6—C1	119.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2^i	0.93	2.63	3.531 (5)	163
C8—H8B···O1^ii	0.97	2.62	3.443 (5)	143
C10—H10B···O2^ii	0.97	2.60	3.483 (5)	151

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