N-(tert-Butyl­oxy­carbonyl­amino)­phthal­imide

An X-ray crystallographic study reveals a short N—N bond in the title compound, C₁₃H₁₄N₂O₄. The molecular packing is mainly driven by strong N—H...O=C hydrogen bonds, leading to C(5) infinite chains, and by π–π stacking interactions between the phthal­imide ring systems.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.046
• wR factor = 0.129
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: COLLECT; data reduction: HKL SUITE (Otwinoski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and WebLab ViewerPro 3.5 (MSI, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 1990).

(I)

Crystal data

C13H14N2O4	F(000) = 552
Mr = 262.26	Dx = 1.296 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10577 reflections
a = 9.7050 (6) Å	θ = 3.4–25.4°
b = 8.5290 (4) Å	µ = 0.10 mm^−1
c = 16.312 (1) Å	T = 293 K
β = 95.275 (3)°	Prism, colorless
V = 1344.49 (13) Å^3	0.2 × 0.1 × 0.1 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	1701 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
Graphite monochromator	θmax = 25.4°, θmin = 3.4°
φ and ω scans	h = −11→11
11015 measured reflections	k = −10→10
2444 independent reflections	l = −19→19

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0577P)^2 + 0.2922P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.046	(Δ/σ)max < 0.001
wR(F^2) = 0.129	Δρmax = 0.20 e Å^−3
S = 1.04	Δρmin = −0.13 e Å^−3
2444 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
173 parameters	Extinction coefficient: 0.044 (5)
0 restraints

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.

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

	x	y	z	Uiso*/Ueq
C1	0.4357 (2)	0.3969 (2)	0.15605 (12)	0.0606 (5)
C2	0.3752 (3)	0.5502 (3)	0.12290 (15)	0.0808 (7)
H2A	0.3487	0.6131	0.1677	0.121*
H2B	0.2953	0.5294	0.0852	0.121*
H2C	0.4431	0.6054	0.0948	0.121*
C3	0.4787 (3)	0.2943 (3)	0.08740 (15)	0.0827 (7)
H3A	0.4022	0.282	0.0463	0.124*
H3B	0.5066	0.1935	0.1091	0.124*
H3C	0.5547	0.3424	0.0632	0.124*
C4	0.5534 (3)	0.4194 (3)	0.22239 (16)	0.0921 (8)
H4A	0.5232	0.4849	0.2651	0.138*
H4B	0.63	0.4682	0.1991	0.138*
H4C	0.5817	0.3193	0.245	0.138*
O1	0.32387 (13)	0.30144 (15)	0.18812 (8)	0.0603 (4)
C5	0.2605 (2)	0.3501 (2)	0.25251 (12)	0.0579 (5)
O2	0.28040 (18)	0.46698 (19)	0.29248 (10)	0.0830 (5)
N1	0.16120 (18)	0.2415 (2)	0.26612 (10)	0.0639 (5)
H1	0.1469	0.1625	0.2337	0.077*
N2	0.08493 (16)	0.26069 (19)	0.33216 (10)	0.0571 (5)
C6	−0.0313 (2)	0.3560 (2)	0.33006 (12)	0.0545 (5)
O3	−0.07743 (17)	0.42941 (18)	0.27051 (9)	0.0748 (5)
C7	−0.0778 (2)	0.3457 (2)	0.41364 (12)	0.0535 (5)
C8	−0.1872 (2)	0.4196 (3)	0.44588 (14)	0.0676 (6)
H8	−0.246	0.4863	0.4141	0.081*
C9	−0.2056 (3)	0.3901 (3)	0.52762 (16)	0.0806 (8)
H9	−0.2776	0.4392	0.5515	0.097*
C10	−0.1196 (3)	0.2898 (3)	0.57418 (15)	0.0844 (8)
H10	−0.1359	0.2707	0.6286	0.101*
C11	−0.0095 (3)	0.2166 (3)	0.54196 (14)	0.0740 (7)
H11	0.0491	0.1493	0.5737	0.089*
C12	0.0101 (2)	0.2474 (2)	0.46067 (12)	0.0549 (5)
C13	0.1194 (2)	0.1924 (2)	0.40982 (13)	0.0585 (5)
O4	0.21798 (17)	0.1090 (2)	0.42608 (10)	0.0854 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0559 (12)	0.0671 (13)	0.0610 (12)	−0.0062 (10)	0.0167 (10)	0.0076 (10)
C2	0.0952 (18)	0.0745 (15)	0.0742 (15)	0.0013 (13)	0.0151 (13)	0.0103 (12)
C3	0.0826 (17)	0.0918 (17)	0.0799 (16)	0.0077 (13)	0.0409 (13)	0.0049 (13)
C4	0.0707 (15)	0.110 (2)	0.0937 (18)	−0.0202 (14)	−0.0033 (14)	0.0192 (15)
O1	0.0622 (9)	0.0641 (8)	0.0583 (8)	−0.0084 (6)	0.0246 (7)	−0.0107 (6)
C5	0.0626 (13)	0.0594 (12)	0.0541 (11)	−0.0030 (10)	0.0182 (10)	−0.0058 (10)
O2	0.1049 (13)	0.0725 (10)	0.0767 (10)	−0.0236 (9)	0.0360 (9)	−0.0277 (8)
N1	0.0693 (11)	0.0621 (10)	0.0650 (11)	−0.0071 (9)	0.0319 (9)	−0.0140 (8)
N2	0.0585 (10)	0.0619 (10)	0.0536 (10)	0.0058 (8)	0.0197 (8)	0.0020 (8)
C6	0.0590 (12)	0.0495 (10)	0.0564 (12)	−0.0006 (9)	0.0130 (10)	−0.0027 (10)
O3	0.0899 (11)	0.0728 (10)	0.0624 (9)	0.0177 (8)	0.0111 (8)	0.0093 (8)
C7	0.0550 (11)	0.0519 (11)	0.0560 (11)	−0.0099 (9)	0.0178 (9)	−0.0079 (9)
C8	0.0616 (13)	0.0700 (14)	0.0746 (14)	−0.0074 (10)	0.0255 (11)	−0.0149 (11)
C9	0.0804 (17)	0.0826 (16)	0.0862 (18)	−0.0248 (14)	0.0469 (15)	−0.0275 (14)
C10	0.105 (2)	0.0929 (18)	0.0614 (14)	−0.0388 (16)	0.0381 (15)	−0.0136 (14)
C11	0.0900 (17)	0.0761 (15)	0.0567 (13)	−0.0211 (13)	0.0121 (12)	0.0047 (11)
C12	0.0599 (12)	0.0559 (11)	0.0505 (11)	−0.0129 (9)	0.0133 (9)	−0.0018 (9)
C13	0.0553 (12)	0.0568 (12)	0.0635 (13)	−0.0035 (10)	0.0066 (10)	0.0001 (10)
O4	0.0734 (11)	0.0916 (11)	0.0907 (12)	0.0211 (9)	0.0041 (9)	0.0089 (9)

Geometric parameters (Å, º)

C1—O1	1.490 (2)	N1—H1	0.86
C1—C3	1.510 (3)	N2—C6	1.388 (2)
C1—C4	1.512 (3)	N2—C13	1.407 (3)
C1—C2	1.513 (3)	C6—O3	1.207 (2)
C2—H2A	0.96	C6—C7	1.477 (3)
C2—H2B	0.96	C7—C12	1.378 (3)
C2—H2C	0.96	C7—C8	1.380 (3)
C3—H3A	0.96	C8—C9	1.384 (3)
C3—H3B	0.96	C8—H8	0.93
C3—H3C	0.96	C9—C10	1.375 (4)
C4—H4A	0.96	C9—H9	0.93
C4—H4B	0.96	C10—C11	1.383 (4)
C4—H4C	0.96	C10—H10	0.93
O1—C5	1.332 (2)	C11—C12	1.382 (3)
C5—O2	1.197 (2)	C11—H11	0.93
C5—N1	1.369 (3)	C12—C13	1.482 (3)
N1—N2	1.372 (2)	C13—O4	1.202 (2)
O1—C1—C3	101.77 (16)	C5—N1—H1	120.5
O1—C1—C4	110.17 (17)	N2—N1—H1	120.5
C3—C1—C4	111.2 (2)	N1—N2—C6	123.11 (16)
O1—C1—C2	109.04 (17)	N1—N2—C13	123.86 (16)
C3—C1—C2	111.13 (19)	C6—N2—C13	112.96 (16)
C4—C1—C2	112.9 (2)	O3—C6—N2	124.34 (18)
C1—C2—H2A	109.5	O3—C6—C7	130.67 (18)
C1—C2—H2B	109.5	N2—C6—C7	104.99 (17)
H2A—C2—H2B	109.5	C12—C7—C8	121.60 (18)
C1—C2—H2C	109.5	C12—C7—C6	108.93 (17)
H2A—C2—H2C	109.5	C8—C7—C6	129.5 (2)
H2B—C2—H2C	109.5	C7—C8—C9	117.2 (2)
C1—C3—H3A	109.5	C7—C8—H8	121.4
C1—C3—H3B	109.5	C9—C8—H8	121.4
H3A—C3—H3B	109.5	C10—C9—C8	121.3 (2)
C1—C3—H3C	109.5	C10—C9—H9	119.4
H3A—C3—H3C	109.5	C8—C9—H9	119.4
H3B—C3—H3C	109.5	C9—C10—C11	121.5 (2)
C1—C4—H4A	109.5	C9—C10—H10	119.2
C1—C4—H4B	109.5	C11—C10—H10	119.2
H4A—C4—H4B	109.5	C12—C11—C10	117.2 (2)
C1—C4—H4C	109.5	C12—C11—H11	121.4
H4A—C4—H4C	109.5	C10—C11—H11	121.4
H4B—C4—H4C	109.5	C7—C12—C11	121.2 (2)
C5—O1—C1	120.74 (15)	C7—C12—C13	108.62 (17)
O2—C5—O1	128.76 (19)	C11—C12—C13	130.2 (2)
O2—C5—N1	123.76 (18)	O4—C13—N2	124.22 (19)
O1—C5—N1	107.47 (17)	O4—C13—C12	131.3 (2)
C5—N1—N2	119.04 (16)	N2—C13—C12	104.46 (17)
C3—C1—O1—C5	177.78 (18)	C6—C7—C8—C9	−178.89 (19)
C4—C1—O1—C5	59.7 (2)	C7—C8—C9—C10	−0.9 (3)
C2—C1—O1—C5	−64.7 (2)	C8—C9—C10—C11	1.4 (4)
C1—O1—C5—O2	−0.4 (3)	C9—C10—C11—C12	−0.5 (3)
C1—O1—C5—N1	178.36 (16)	C8—C7—C12—C11	1.2 (3)
O2—C5—N1—N2	−4.2 (3)	C6—C7—C12—C11	179.99 (17)
O1—C5—N1—N2	176.89 (16)	C8—C7—C12—C13	−177.60 (17)
C5—N1—N2—C6	83.5 (2)	C6—C7—C12—C13	1.2 (2)
C5—N1—N2—C13	−93.4 (2)	C10—C11—C12—C7	−0.7 (3)
N1—N2—C6—O3	0.8 (3)	C10—C11—C12—C13	177.8 (2)
C13—N2—C6—O3	178.05 (18)	N1—N2—C13—O4	−0.9 (3)
N1—N2—C6—C7	−178.43 (16)	C6—N2—C13—O4	−178.06 (19)
C13—N2—C6—C7	−1.2 (2)	N1—N2—C13—C12	179.10 (16)
O3—C6—C7—C12	−179.3 (2)	C6—N2—C13—C12	1.9 (2)
N2—C6—C7—C12	−0.1 (2)	C7—C12—C13—O4	178.1 (2)
O3—C6—C7—C8	−0.6 (4)	C11—C12—C13—O4	−0.5 (4)
N2—C6—C7—C8	178.63 (19)	C7—C12—C13—N2	−1.9 (2)
C12—C7—C8—C9	−0.4 (3)	C11—C12—C13—N2	179.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3^i	0.86	2.10	2.831 (2)	143

Symmetry code: (i) −x, y−1/2, −z+1/2.