N,N,N′-Triacetyl-2,6-diamino-4-tert-butyl­anisole

The solid state structure of the title compound, C₁₇H₂₄N₂O₄, reveals the imide unit to be planar and perpendicular to the plane of the benzene ring. In the crystal structure, adjacent mol­ecules are hydrogen bonded through the amide unit.

Key indicators

• Single-crystal X-ray study
• T = 93 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.034
• wR factor = 0.089
• Data-to-parameter ratio = 8.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.10 Ratio

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.37 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C8

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           26.42
           From the CIF: _reflns_number_total               1934
           Count of symmetry unique reflns         1939
           Completeness (_total/calc)             99.74%
           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
   1 ALERT level B = Potentially serious problem
   2 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: APEXII (Bruker 2004); cell refinement: APEXII; data reduction: APEXII; program(s) used to solve structure: APEXII; program(s) used to refine structure: APEXII; molecular graphics: ORTEP-3 (Version 1.08; Farrugia, 1997) and Mercury (Version Bruno et al., 2002); software used to prepare material for publication: enCIFer (Version 1.1; Allen et al., 2004).

N,N,N'-Triacetyl-2,6-diamino-4-t-butylanisole

Crystal data

C17H24N2O4	Dx = 1.210 Mg m^−3
Mr = 320.38	Melting point: 452 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 10745 reflections
a = 9.9409 (6) Å	θ = 2.6–26.4°
b = 20.9722 (14) Å	µ = 0.09 mm^−1
c = 8.4392 (6) Å	T = 93 K
V = 1759.4 (2) Å^3	Block, colourless
Z = 4	0.59 × 0.52 × 0.35 mm
F(000) = 688

Data collection

Bruker APEX-II CCD area-detector diffractometer	1934 independent reflections
Radiation source: sealed tube	1858 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan (APEXII; Bruker, 2004)	h = −12→12
Tmin = 0.877, Tmax = 0.970	k = −26→23
14772 measured reflections	l = −10→10

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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.089	w = 1/[σ^2(Fo^2) + (0.0562P)^2 + 0.5007P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
1934 reflections	Δρmax = 0.30 e Å^−3
218 parameters	Δρmin = −0.33 e Å^−3
13 restraints	Absolute structure: Friedel pairs were merged
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.14160 (16)	0.64898 (8)	0.6336 (2)	0.0212 (4)
O2	0.04407 (18)	0.48028 (8)	0.7138 (2)	0.0267 (4)
O3	0.25199 (18)	0.56720 (9)	1.0754 (3)	0.0276 (4)
O4	−0.26100 (16)	0.74736 (9)	0.3937 (2)	0.0229 (4)
N1	0.08842 (19)	0.56195 (9)	0.8812 (2)	0.0171 (4)
N2	−0.05543 (19)	0.71921 (9)	0.4951 (3)	0.0176 (4)
H2	0.027 (3)	0.7238 (13)	0.489 (4)	0.021*
C1	0.0103 (2)	0.63942 (11)	0.6831 (3)	0.0166 (5)
C2	−0.0194 (2)	0.59699 (11)	0.8045 (3)	0.0166 (5)
C3	−0.1510 (2)	0.58850 (10)	0.8568 (3)	0.0169 (5)
H3A	−0.1696	0.5582	0.9375	0.020*
C4	−0.2557 (2)	0.62414 (11)	0.7917 (3)	0.0166 (5)
C5	−0.2249 (2)	0.66876 (11)	0.6725 (3)	0.0163 (4)
H5A	−0.2948	0.6942	0.6290	0.020*
C6	−0.0935 (2)	0.67631 (11)	0.6167 (3)	0.0164 (5)
C7	0.1830 (3)	0.60510 (13)	0.5110 (4)	0.0296 (6)
H7A	0.2765	0.6139	0.4814	0.044*
H7B	0.1249	0.6104	0.4181	0.044*
H7C	0.1756	0.5613	0.5505	0.044*
C8	−0.4025 (2)	0.61306 (11)	0.8433 (3)	0.0199 (5)
C9	−0.4801 (3)	0.67577 (15)	0.8528 (5)	0.0434 (9)
H9A	−0.5711	0.6676	0.8928	0.065*
H9B	−0.4857	0.6949	0.7470	0.065*
H9C	−0.4335	0.7051	0.9246	0.065*
C10	−0.4106 (3)	0.58154 (19)	1.0061 (5)	0.0474 (8)
H10A	−0.5048	0.5792	1.0398	0.071*
H10B	−0.3592	0.6068	1.0828	0.071*
H10C	−0.3729	0.5384	1.0001	0.071*
C11	−0.4707 (4)	0.57000 (19)	0.7208 (5)	0.0549 (10)
H11A	−0.5650	0.5635	0.7505	0.082*
H11B	−0.4245	0.5288	0.7173	0.082*
H11C	−0.4663	0.5902	0.6162	0.082*
C12	0.1094 (2)	0.49899 (11)	0.8272 (3)	0.0197 (5)
C13	0.2089 (3)	0.45700 (12)	0.9112 (3)	0.0264 (5)
H13A	0.2067	0.4142	0.8647	0.040*
H13B	0.1854	0.4544	1.0238	0.040*
H13C	0.2994	0.4750	0.9000	0.040*
C14	0.1561 (2)	0.59126 (11)	1.0103 (3)	0.0197 (5)
C15	0.1013 (3)	0.65524 (12)	1.0600 (4)	0.0294 (6)
H15A	0.1534	0.6714	1.1500	0.044*
H15B	0.0068	0.6507	1.0911	0.044*
H15C	0.1082	0.6852	0.9713	0.044*
C16	−0.1375 (2)	0.75127 (11)	0.3921 (3)	0.0185 (4)
C17	−0.0641 (3)	0.79204 (14)	0.2725 (4)	0.0307 (6)
H17A	−0.1295	0.8138	0.2045	0.046*	0.20 (4)
H17B	−0.0058	0.7650	0.2072	0.046*	0.20 (4)
H17C	−0.0092	0.8238	0.3280	0.046*	0.20 (4)
H17D	0.0331	0.7889	0.2906	0.046*	0.80 (4)
H17E	−0.0925	0.8365	0.2839	0.046*	0.80 (4)
H17F	−0.0851	0.7771	0.1652	0.046*	0.80 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0142 (8)	0.0278 (9)	0.0216 (8)	−0.0017 (7)	0.0004 (7)	0.0042 (7)
O2	0.0308 (9)	0.0241 (9)	0.0250 (10)	0.0017 (7)	−0.0051 (8)	−0.0022 (8)
O3	0.0197 (8)	0.0322 (10)	0.0309 (10)	0.0001 (7)	−0.0089 (8)	0.0037 (8)
O4	0.0167 (7)	0.0296 (9)	0.0223 (9)	0.0030 (7)	−0.0006 (8)	0.0051 (8)
N1	0.0148 (9)	0.0188 (9)	0.0177 (10)	0.0004 (7)	−0.0007 (8)	0.0022 (8)
N2	0.0134 (9)	0.0211 (10)	0.0184 (10)	−0.0015 (7)	−0.0006 (8)	0.0028 (8)
C1	0.0126 (10)	0.0198 (10)	0.0173 (11)	−0.0021 (8)	−0.0015 (9)	−0.0021 (9)
C2	0.0171 (11)	0.0172 (10)	0.0155 (11)	0.0003 (8)	−0.0026 (9)	−0.0008 (9)
C3	0.0173 (11)	0.0162 (10)	0.0170 (11)	−0.0024 (8)	0.0013 (9)	0.0011 (9)
C4	0.0162 (10)	0.0165 (11)	0.0172 (11)	−0.0016 (8)	0.0008 (9)	−0.0017 (9)
C5	0.0165 (10)	0.0161 (10)	0.0162 (11)	0.0003 (8)	−0.0020 (9)	−0.0006 (8)
C6	0.0186 (10)	0.0159 (10)	0.0147 (11)	−0.0021 (8)	−0.0010 (9)	0.0002 (9)
C7	0.0272 (13)	0.0281 (13)	0.0336 (15)	0.0050 (10)	0.0121 (12)	0.0069 (12)
C8	0.0147 (10)	0.0217 (11)	0.0232 (12)	−0.0008 (9)	0.0029 (10)	−0.0005 (10)
C9	0.0342 (15)	0.0343 (15)	0.062 (2)	0.0129 (12)	0.0294 (16)	0.0171 (16)
C10	0.0306 (13)	0.0624 (17)	0.0493 (16)	0.0067 (13)	0.0102 (14)	0.0298 (15)
C11	0.0362 (14)	0.0690 (18)	0.0595 (18)	−0.0195 (14)	0.0132 (14)	−0.0304 (16)
C12	0.0201 (11)	0.0199 (11)	0.0192 (11)	−0.0009 (9)	0.0043 (10)	0.0041 (10)
C13	0.0290 (13)	0.0242 (12)	0.0260 (13)	0.0043 (10)	−0.0023 (11)	0.0053 (11)
C14	0.0151 (10)	0.0241 (12)	0.0198 (12)	−0.0034 (9)	0.0000 (10)	0.0033 (9)
C15	0.0338 (14)	0.0251 (13)	0.0294 (14)	0.0014 (11)	−0.0120 (12)	−0.0053 (11)
C16	0.0181 (10)	0.0194 (10)	0.0179 (11)	0.0031 (8)	0.0023 (10)	0.0012 (9)
C17	0.0222 (12)	0.0387 (15)	0.0311 (14)	0.0076 (11)	0.0093 (11)	0.0179 (13)

Geometric parameters (Å, º)

O1—C1	1.385 (3)	C8—C11	1.531 (4)
O1—C7	1.444 (3)	C9—H9A	0.9800
O2—C12	1.221 (3)	C9—H9B	0.9800
O3—C14	1.211 (3)	C9—H9C	0.9800
O4—C16	1.231 (3)	C10—H10A	0.9800
N1—C12	1.412 (3)	C10—H10B	0.9800
N1—C14	1.420 (3)	C10—H10C	0.9800
N1—C2	1.452 (3)	C11—H11A	0.9800
N2—C16	1.369 (3)	C11—H11B	0.9800
N2—C6	1.416 (3)	C11—H11C	0.9800
N2—H2	0.83 (3)	C12—C13	1.502 (3)
C1—C2	1.389 (3)	C13—H13A	0.9800
C1—C6	1.406 (3)	C13—H13B	0.9800
C2—C3	1.393 (3)	C13—H13C	0.9800
C3—C4	1.394 (3)	C14—C15	1.507 (4)
C3—H3A	0.9500	C15—H15A	0.9800
C4—C5	1.408 (3)	C15—H15B	0.9800
C4—C8	1.541 (3)	C15—H15C	0.9800
C5—C6	1.398 (3)	C16—C17	1.511 (3)
C5—H5A	0.9500	C17—H17A	0.9800
C7—H7A	0.9800	C17—H17B	0.9800
C7—H7B	0.9800	C17—H17C	0.9800
C7—H7C	0.9800	C17—H17D	0.9800
C8—C10	1.526 (4)	C17—H17E	0.9800
C8—C9	1.527 (4)	C17—H17F	0.9800
C1—O1—C7	113.11 (19)	C8—C10—H10A	109.5
C12—N1—C14	125.6 (2)	C8—C10—H10B	109.5
C12—N1—C2	115.97 (19)	H10A—C10—H10B	109.5
C14—N1—C2	118.22 (19)	C8—C10—H10C	109.5
C16—N2—C6	127.8 (2)	H10A—C10—H10C	109.5
C16—N2—H2	119 (2)	H10B—C10—H10C	109.5
C6—N2—H2	113 (2)	C8—C11—H11A	109.5
O1—C1—C2	121.1 (2)	C8—C11—H11B	109.5
O1—C1—C6	119.4 (2)	H11A—C11—H11B	109.5
C2—C1—C6	119.4 (2)	C8—C11—H11C	109.5
C1—C2—C3	121.0 (2)	H11A—C11—H11C	109.5
C1—C2—N1	119.8 (2)	H11B—C11—H11C	109.5
C3—C2—N1	119.2 (2)	O2—C12—N1	118.4 (2)
C2—C3—C4	120.5 (2)	O2—C12—C13	122.1 (2)
C2—C3—H3A	119.7	N1—C12—C13	119.5 (2)
C4—C3—H3A	119.7	C12—C13—H13A	109.5
C3—C4—C5	118.4 (2)	C12—C13—H13B	109.5
C3—C4—C8	121.0 (2)	H13A—C13—H13B	109.5
C5—C4—C8	120.6 (2)	C12—C13—H13C	109.5
C6—C5—C4	121.3 (2)	H13A—C13—H13C	109.5
C6—C5—H5A	119.4	H13B—C13—H13C	109.5
C4—C5—H5A	119.4	O3—C14—N1	122.7 (2)
C5—C6—C1	119.3 (2)	O3—C14—C15	121.9 (2)
C5—C6—N2	124.4 (2)	N1—C14—C15	115.3 (2)
C1—C6—N2	116.3 (2)	C14—C15—H15A	109.5
O1—C7—H7A	109.5	C14—C15—H15B	109.5
O1—C7—H7B	109.5	H15A—C15—H15B	109.5
H7A—C7—H7B	109.5	C14—C15—H15C	109.5
O1—C7—H7C	109.5	H15A—C15—H15C	109.5
H7A—C7—H7C	109.5	H15B—C15—H15C	109.5
H7B—C7—H7C	109.5	O4—C16—N2	123.7 (2)
C10—C8—C9	107.4 (3)	O4—C16—C17	121.8 (2)
C10—C8—C11	109.2 (3)	N2—C16—C17	114.5 (2)
C9—C8—C11	108.7 (3)	C16—C17—H17A	109.5
C10—C8—C4	111.7 (2)	C16—C17—H17B	109.5
C9—C8—C4	111.3 (2)	C16—C17—H17C	109.5
C11—C8—C4	108.5 (2)	C16—C17—H17D	109.5
C8—C9—H9A	109.5	C16—C17—H17E	109.5
C8—C9—H9B	109.5	H17D—C17—H17E	109.5
H9A—C9—H9B	109.5	C16—C17—H17F	109.5
C8—C9—H9C	109.5	H17D—C17—H17F	109.5
H9A—C9—H9C	109.5	H17E—C17—H17F	109.5
H9B—C9—H9C	109.5
C7—O1—C1—C2	88.4 (3)	O1—C1—C6—N2	3.3 (3)
C7—O1—C1—C6	−95.8 (3)	C2—C1—C6—N2	179.1 (2)
O1—C1—C2—C3	178.5 (2)	C16—N2—C6—C5	−13.1 (4)
C6—C1—C2—C3	2.7 (3)	C16—N2—C6—C1	166.7 (2)
O1—C1—C2—N1	0.0 (3)	C3—C4—C8—C10	22.2 (3)
C6—C1—C2—N1	−175.7 (2)	C5—C4—C8—C10	−160.6 (3)
C12—N1—C2—C1	−98.3 (2)	C3—C4—C8—C9	142.2 (3)
C14—N1—C2—C1	86.5 (3)	C5—C4—C8—C9	−40.5 (3)
C12—N1—C2—C3	83.3 (3)	C3—C4—C8—C11	−98.3 (3)
C14—N1—C2—C3	−92.0 (3)	C5—C4—C8—C11	79.0 (3)
C1—C2—C3—C4	−2.1 (3)	C14—N1—C12—O2	−179.6 (2)
N1—C2—C3—C4	176.3 (2)	C2—N1—C12—O2	5.5 (3)
C2—C3—C4—C5	−0.1 (3)	C14—N1—C12—C13	1.2 (3)
C2—C3—C4—C8	177.2 (2)	C2—N1—C12—C13	−173.6 (2)
C3—C4—C5—C6	1.7 (3)	C12—N1—C14—O3	9.6 (4)
C8—C4—C5—C6	−175.6 (2)	C2—N1—C14—O3	−175.7 (2)
C4—C5—C6—C1	−1.2 (3)	C12—N1—C14—C15	−171.2 (2)
C4—C5—C6—N2	178.7 (2)	C2—N1—C14—C15	3.6 (3)
O1—C1—C6—C5	−176.9 (2)	C6—N2—C16—O4	1.1 (4)
C2—C1—C6—C5	−1.0 (3)	C6—N2—C16—C17	−178.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.83 (3)	2.29 (3)	2.715 (3)	112 (3)
N2—H2···O4^i	0.83 (3)	2.33 (3)	3.129 (3)	161 (3)

Symmetry code: (i) x+1/2, −y+3/2, z.