N-[6-(2,2-Di­methyl­propionyl­amino)­pyridin-2-yl]-2,2-di­methyl­propion­amide

At 150 K, only one of the two amide groups of the title compound, C₁₅H₂₃N₃O₂, is involved in weak hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.033
• wR factor = 0.072
• Data-to-parameter ratio = 19.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor       N2     -   H2     ...          ?

   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: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2001); program(s) used to solve structure: X-STEP32 (Stoe & Cie, 2001) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: WinGX (Farrugia, 1999) and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

N-[6-(2,2-Dimethylpropionylamino)pyridin-2-yl]-2,2-dimethylpropionamide

Crystal data

C15H23N3O2	F(000) = 600
Mr = 277.36	Dx = 1.176 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10680 reflections
a = 11.4234 (13) Å	θ = 2.6–27.5°
b = 15.1383 (19) Å	µ = 0.08 mm^−1
c = 9.3774 (10) Å	T = 150 K
β = 104.885 (9)°	Needle, colourless
V = 1567.2 (3) Å^3	0.50 × 0.20 × 0.10 mm
Z = 4

Data collection

Stoe IPDS-II area-detector diffractometer	2174 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.060
Graphite monochromator	θmax = 27.5°, θmin = 2.6°
Area detector scans	h = −14→14
22744 measured reflections	k = −19→19
3601 independent reflections	l = −10→12

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)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.072	w = 1/[σ^2(Fo^2) + (0.0372P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.80	(Δ/σ)max < 0.001
3601 reflections	Δρmax = 0.19 e Å^−3
190 parameters	Δρmin = −0.14 e Å^−3
0 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: 0.0101 (10)

Special details

Experimental. The crystal was mounted under the perfluoro-polyether PFO-XR75 (Lancaster Synthesis). A total of 320 frames (2 minute exposure) were collected (phi/omega: 0/10–170, 135/10–170, delta-omega = 1 °.)

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.

Weighted least-squares planes through the starred atoms (Nardelli, Musatti, Domiano & Andreetti Ric·Sci.(1965),15(II—A),807). Equation of the plane: m1*X+m2*Y+m3*Z=d

Plane 1 m1 = 0.80329(0.00031) m2 = -0.55618(0.00041) m3 = -0.21305(0.00048) D = -0.98660(0.00255) Atom d s d/s (d/s)**2 N1 * 0.0071 0.0010 7.072 50.007 C1 * -0.0143 0.0012 - 11.927 142.262 C2 * 0.0071 0.0012 5.867 34.424 C3 * 0.0042 0.0013 3.252 10.578 C4 * -0.0090 0.0013 - 6.791 46.116 C5 * 0.0008 0.0012 0.690 0.476 N2 - 0.0389 0.0011 - 34.591 1196.515 N3 - 0.0561 0.0012 - 47.048 2213.499 ============ Sum((d/s)**2) for starred atoms 283.863 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarity

Plane 2 m1 = -0.40324(0.00064) m2 = 0.85647(0.00075) m3 = 0.32227(0.00217) D = 2.11922(0.00226) Atom d s d/s (d/s)**2 C6 * 0.0000 0.0012 0.000 0.000 O1 * 0.0000 0.0009 0.000 0.000 N2 * 0.0000 0.0012 0.000 0.000 C1 0.1534 0.0012 127.095 16153.201 C7 0.0301 0.0012 24.540 602.188 ============ Sum((d/s)**2) for starred atoms 0.000

Plane 3 m1 = 0.84812(0.00120) m2 = -0.44459(0.00203) m3 = -0.28815(0.00073) D = -0.90977(0.01409) Atom d s d/s (d/s)**2 C11 * 0.0000 0.0012 0.000 0.000 O2 * 0.0000 0.0009 0.000 0.000 N3 * 0.0000 0.0012 0.000 0.000 C5 - 0.0652 0.0012 - 54.448 2964.621 C12 0.0221 0.0014 16.187 262.018 ============ Sum((d/s)**2) for starred atoms 0.000

Dihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1 2 29.67 (0.05) 150.33 (0.05) 1 3 8.13 (0.11) 171.87 (0.11) 2 3 35.35 (0.11) 144.65 (0.11)

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
O1	−0.08450 (7)	0.07892 (6)	0.18159 (10)	0.0346 (2)
O2	0.45687 (7)	0.21044 (6)	0.84217 (9)	0.0341 (2)
N1	0.23611 (8)	0.18425 (7)	0.41255 (11)	0.0264 (2)
N2	0.10043 (9)	0.13848 (8)	0.20205 (12)	0.0296 (3)
H2	0.1372 (14)	0.1735 (11)	0.1646 (17)	0.044 (5)*
N3	0.36988 (10)	0.24908 (8)	0.60522 (12)	0.0322 (3)
H3	0.3802 (13)	0.2802 (10)	0.5319 (17)	0.043 (4)*
C1	0.15320 (10)	0.12370 (8)	0.35315 (13)	0.0258 (3)
C2	0.12360 (10)	0.05306 (8)	0.43120 (14)	0.0279 (3)
H2A	0.0661	0.0098	0.3847	0.033*
C3	0.18150 (11)	0.04836 (8)	0.57963 (14)	0.0296 (3)
H3A	0.1632	0.0012	0.6371	0.035*
C4	0.26576 (11)	0.11132 (9)	0.64592 (14)	0.0298 (3)
H4A	0.3049	0.1088	0.7483	0.036*
C5	0.29085 (10)	0.17827 (8)	0.55712 (13)	0.0258 (3)
C6	−0.01614 (10)	0.11996 (8)	0.12578 (13)	0.0249 (3)
C7	−0.05457 (11)	0.15600 (8)	−0.03204 (13)	0.0283 (3)
C8	−0.17321 (12)	0.11076 (10)	−0.11259 (15)	0.0392 (3)
H8A	−0.1605	0.0468	−0.1143	0.047*
H8B	−0.1992	0.1330	−0.2140	0.047*
H8C	−0.2358	0.1235	−0.0610	0.047*
C9	0.04227 (12)	0.13786 (9)	−0.11518 (14)	0.0349 (3)
H9A	0.1184	0.1663	−0.0634	0.042*
H9B	0.0154	0.1617	−0.2155	0.042*
H9C	0.0549	0.0740	−0.1198	0.042*
C10	−0.07488 (12)	0.25575 (9)	−0.02261 (15)	0.0348 (3)
H10A	−0.1382	0.2665	0.0288	0.042*
H10B	−0.1001	0.2805	−0.1224	0.042*
H10C	0.0006	0.2840	0.0318	0.042*
C11	0.44589 (10)	0.26390 (9)	0.74201 (14)	0.0293 (3)
C12	0.51668 (11)	0.35106 (10)	0.75859 (15)	0.0357 (3)
C13	0.56619 (15)	0.37116 (12)	0.92231 (17)	0.0549 (5)
H13A	0.4988	0.3766	0.9687	0.066*
H13B	0.6117	0.4267	0.9341	0.066*
H13C	0.6198	0.3231	0.9694	0.066*
C14	0.62309 (13)	0.33889 (13)	0.68893 (17)	0.0514 (4)
H14A	0.6750	0.2908	0.7392	0.062*
H14B	0.6702	0.3937	0.6989	0.062*
H14C	0.5922	0.3244	0.5841	0.062*
C15	0.43737 (14)	0.42753 (11)	0.6840 (2)	0.0603 (5)
H15A	0.4057	0.4147	0.5787	0.072*
H15B	0.4857	0.4818	0.6960	0.072*
H15C	0.3697	0.4353	0.7294	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0310 (4)	0.0416 (5)	0.0307 (5)	−0.0075 (4)	0.0070 (4)	0.0074 (4)
O2	0.0302 (5)	0.0466 (6)	0.0236 (5)	0.0026 (4)	0.0037 (4)	0.0016 (4)
N1	0.0250 (5)	0.0322 (6)	0.0217 (5)	−0.0015 (4)	0.0053 (4)	0.0015 (4)
N2	0.0298 (5)	0.0370 (6)	0.0213 (5)	−0.0088 (5)	0.0054 (4)	0.0043 (5)
N3	0.0339 (6)	0.0396 (7)	0.0218 (5)	−0.0088 (5)	0.0049 (5)	0.0035 (5)
C1	0.0239 (5)	0.0300 (7)	0.0232 (6)	0.0016 (5)	0.0058 (5)	0.0001 (5)
C2	0.0270 (6)	0.0276 (7)	0.0287 (7)	−0.0002 (5)	0.0067 (5)	0.0025 (5)
C3	0.0291 (6)	0.0302 (7)	0.0303 (7)	0.0039 (5)	0.0094 (5)	0.0084 (6)
C4	0.0288 (6)	0.0378 (7)	0.0226 (6)	0.0041 (5)	0.0062 (5)	0.0052 (6)
C5	0.0227 (6)	0.0328 (7)	0.0217 (6)	0.0012 (5)	0.0057 (5)	0.0006 (5)
C6	0.0276 (6)	0.0229 (6)	0.0243 (6)	−0.0010 (5)	0.0067 (5)	−0.0032 (5)
C7	0.0319 (6)	0.0293 (7)	0.0224 (6)	−0.0045 (5)	0.0046 (5)	0.0006 (5)
C8	0.0400 (7)	0.0450 (8)	0.0274 (7)	−0.0090 (6)	−0.0004 (6)	0.0012 (6)
C9	0.0449 (7)	0.0372 (8)	0.0236 (6)	−0.0031 (6)	0.0104 (6)	0.0008 (6)
C10	0.0388 (7)	0.0335 (7)	0.0289 (6)	0.0015 (6)	0.0028 (6)	0.0035 (6)
C11	0.0217 (6)	0.0432 (8)	0.0234 (6)	0.0016 (5)	0.0064 (5)	−0.0034 (6)
C12	0.0277 (6)	0.0488 (9)	0.0294 (7)	−0.0093 (6)	0.0053 (6)	−0.0035 (6)
C13	0.0611 (10)	0.0700 (12)	0.0356 (8)	−0.0309 (9)	0.0162 (7)	−0.0161 (8)
C14	0.0335 (7)	0.0821 (12)	0.0394 (9)	−0.0188 (7)	0.0106 (6)	−0.0098 (8)
C15	0.0460 (9)	0.0439 (10)	0.0816 (13)	−0.0119 (8)	−0.0009 (9)	0.0006 (9)

Geometric parameters (Å, º)

O1—C6	1.2165 (14)	C8—H8B	0.9800
O2—C11	1.2215 (15)	C8—H8C	0.9800
N1—C1	1.3328 (15)	C9—H9A	0.9800
N1—C5	1.3423 (15)	C9—H9B	0.9800
N2—C6	1.3689 (15)	C9—H9C	0.9800
N2—C1	1.4080 (16)	C10—H10A	0.9800
N2—H2	0.810 (16)	C10—H10B	0.9800
N3—C11	1.3702 (16)	C10—H10C	0.9800
N3—C5	1.3995 (16)	C11—C12	1.5345 (18)
N3—H3	0.866 (16)	C12—C13	1.524 (2)
C1—C2	1.3859 (17)	C12—C15	1.525 (2)
C2—C3	1.3810 (18)	C12—C14	1.532 (2)
C2—H2A	0.9500	C13—H13A	0.9800
C3—C4	1.3834 (18)	C13—H13B	0.9800
C3—H3A	0.9500	C13—H13C	0.9800
C4—C5	1.3875 (18)	C14—H14A	0.9800
C4—H4A	0.9500	C14—H14B	0.9800
C6—C7	1.5319 (17)	C14—H14C	0.9800
C7—C9	1.5329 (18)	C15—H15A	0.9800
C7—C8	1.5331 (17)	C15—H15B	0.9800
C7—C10	1.5338 (19)	C15—H15C	0.9800
C8—H8A	0.9800
C1—N1—C5	118.19 (11)	C7—C9—H9B	109.5
C6—N2—C1	126.92 (11)	H9A—C9—H9B	109.5
C6—N2—H2	116.8 (11)	C7—C9—H9C	109.5
C1—N2—H2	113.9 (11)	H9A—C9—H9C	109.5
C11—N3—C5	128.92 (12)	H9B—C9—H9C	109.5
C11—N3—H3	118.1 (10)	C7—C10—H10A	109.5
C5—N3—H3	111.6 (10)	C7—C10—H10B	109.5
N1—C1—C2	123.61 (11)	H10A—C10—H10B	109.5
N1—C1—N2	112.69 (11)	C7—C10—H10C	109.5
C2—C1—N2	123.68 (11)	H10A—C10—H10C	109.5
C3—C2—C1	116.96 (12)	H10B—C10—H10C	109.5
C3—C2—H2A	121.5	O2—C11—N3	121.78 (12)
C1—C2—H2A	121.5	O2—C11—C12	122.98 (11)
C2—C3—C4	121.01 (12)	N3—C11—C12	115.23 (11)
C2—C3—H3A	119.5	C13—C12—C15	109.48 (14)
C4—C3—H3A	119.5	C13—C12—C14	108.89 (11)
C3—C4—C5	117.43 (11)	C15—C12—C14	109.81 (13)
C3—C4—H4A	121.3	C13—C12—C11	108.86 (12)
C5—C4—H4A	121.3	C15—C12—C11	111.77 (10)
N1—C5—C4	122.75 (11)	C14—C12—C11	107.97 (12)
N1—C5—N3	111.62 (11)	C12—C13—H13A	109.5
C4—C5—N3	125.57 (11)	C12—C13—H13B	109.5
O1—C6—N2	121.71 (11)	H13A—C13—H13B	109.5
O1—C6—C7	122.77 (10)	C12—C13—H13C	109.5
N2—C6—C7	115.51 (11)	H13A—C13—H13C	109.5
C6—C7—C9	111.25 (10)	H13B—C13—H13C	109.5
C6—C7—C8	108.34 (10)	C12—C14—H14A	109.5
C9—C7—C8	109.36 (11)	C12—C14—H14B	109.5
C6—C7—C10	107.76 (10)	H14A—C14—H14B	109.5
C9—C7—C10	110.19 (11)	C12—C14—H14C	109.5
C8—C7—C10	109.91 (11)	H14A—C14—H14C	109.5
C7—C8—H8A	109.5	H14B—C14—H14C	109.5
C7—C8—H8B	109.5	C12—C15—H15A	109.5
H8A—C8—H8B	109.5	C12—C15—H15B	109.5
C7—C8—H8C	109.5	H15A—C15—H15B	109.5
H8A—C8—H8C	109.5	C12—C15—H15C	109.5
H8B—C8—H8C	109.5	H15A—C15—H15C	109.5
C7—C9—H9A	109.5	H15B—C15—H15C	109.5
C5—N1—C1—C2	−2.46 (18)	C1—N2—C6—C7	170.93 (12)
C5—N1—C1—N2	178.51 (10)	O1—C6—C7—C9	−135.40 (12)
C6—N2—C1—N1	−147.04 (12)	N2—C6—C7—C9	45.85 (14)
C6—N2—C1—C2	33.94 (19)	O1—C6—C7—C8	−15.16 (17)
N1—C1—C2—C3	2.27 (18)	N2—C6—C7—C8	166.09 (11)
N2—C1—C2—C3	−178.80 (12)	O1—C6—C7—C10	103.70 (13)
C1—C2—C3—C4	−0.49 (18)	N2—C6—C7—C10	−75.04 (13)
C2—C3—C4—C5	−0.93 (18)	C5—N3—C11—O2	3.4 (2)
C1—N1—C5—C4	0.86 (18)	C5—N3—C11—C12	−177.47 (12)
C1—N1—C5—N3	−176.41 (10)	O2—C11—C12—C13	−17.66 (18)
C3—C4—C5—N1	0.78 (18)	N3—C11—C12—C13	163.26 (12)
C3—C4—C5—N3	177.67 (12)	O2—C11—C12—C15	−138.71 (14)
C11—N3—C5—N1	−176.39 (12)	N3—C11—C12—C15	42.21 (17)
C11—N3—C5—C4	6.4 (2)	O2—C11—C12—C14	100.41 (14)
C1—N2—C6—O1	−7.8 (2)	N3—C11—C12—C14	−78.67 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O2^i	0.866 (15)	2.180 (15)	2.9508 (14)	148.0 (14)

Symmetry code: (i) x, −y+1/2, z−1/2.