N-(5-Cyano­nonan-5-yl)benzamide

N-(5-Cyano­nonan-5-yl)benzamide, C₁₇H₂₄N₂O, synthesized from the reaction between benzoyl chloride and 2-amino-2-butyl­hexa­nenitrile, is an important inter­mediate in amino acid synthesis. Inter­molecular N—H...O and C—H...O hydrogen bonds with N...O and C...O distances of 3.083 (2) and 3.304 (2) Å, respectively, link adjacent mol­ecules into chains along the a axis. The dihedral angle between the mean plane of the phenyl group and the plane of the amide group is 19.504 (4)°.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.043
• wR factor = 0.112
• Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.232 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         29 Report
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          1 Check

Alert level G
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C12      --C17      .        6.4 s.u.
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        107 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        4.7 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   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
   4 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: CrysAlis PRO (Rigaku OD, 2023); cell refinement: CrysAlis PRO (Rigaku OD, 2023); data reduction: CrysAlis PRO (Rigaku OD, 2023); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

N-(5-Cyanononan-5-yl)benzamide

Crystal data

C17H24N2O	Dx = 1.115 Mg m^−3
Mr = 272.38	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pbca	Cell parameters from 10946 reflections
a = 10.3939 (1) Å	θ = 4.3–77.8°
b = 17.6680 (2) Å	µ = 0.54 mm^−1
c = 17.6653 (2) Å	T = 298 K
V = 3244.05 (6) Å^3	Needle, clear light colourless
Z = 8	0.06 × 0.03 × 0.02 mm
F(000) = 1184

Data collection

XtaLAB Synergy, Single source at home/near, HyPix diffractometer	3322 independent reflections
Radiation source: micro-focus sealed X-ray tube	2883 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	Rint = 0.027
ω scans	θmax = 78.0°, θmin = 5.0°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2023)	h = −10→12
Tmin = 0.852, Tmax = 1.000	k = −17→22
15515 measured reflections	l = −22→22

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.112	w = 1/[σ^2(Fo^2) + (0.0401P)^2 + 1.052P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
3322 reflections	Δρmax = 0.24 e Å^−3
188 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Extinction correction: SHELXL2018 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: dual	Extinction coefficient: 0.00252 (16)

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
O1	0.68510 (9)	0.39486 (6)	0.24909 (6)	0.0447 (3)
N2	0.47630 (10)	0.42156 (6)	0.27067 (6)	0.0354 (3)
H2N	0.3976 (15)	0.4095 (8)	0.2635 (9)	0.039 (4)*
N3	0.63961 (13)	0.41287 (9)	0.43755 (8)	0.0585 (4)
C1	0.57087 (12)	0.38404 (7)	0.23375 (7)	0.0346 (3)
C2	0.53211 (12)	0.32919 (7)	0.17351 (7)	0.0370 (3)
C3	0.62231 (15)	0.27549 (8)	0.15148 (9)	0.0458 (3)
H3	0.702073	0.273870	0.175283	0.055*
C4	0.59447 (18)	0.22447 (8)	0.09449 (10)	0.0563 (4)
H4	0.655468	0.188838	0.079870	0.068*
C5	0.4763 (2)	0.22650 (9)	0.05942 (10)	0.0629 (5)
H5	0.457268	0.191991	0.021279	0.075*
C6	0.38608 (18)	0.27953 (10)	0.08067 (10)	0.0618 (4)
H6	0.306382	0.280710	0.056764	0.074*
C7	0.41359 (14)	0.33116 (9)	0.13756 (9)	0.0485 (4)
H7	0.352624	0.367046	0.151570	0.058*
C8	0.13369 (18)	0.42176 (12)	0.51281 (11)	0.0687 (5)
H8A	0.130708	0.369920	0.496635	0.103*
H8B	0.048757	0.438170	0.526484	0.103*
H8C	0.189651	0.426219	0.555814	0.103*
C9	0.18399 (14)	0.47054 (9)	0.44905 (9)	0.0487 (4)
H9A	0.190157	0.522524	0.466342	0.058*
H9B	0.123469	0.469132	0.407272	0.058*
C10	0.31508 (13)	0.44461 (8)	0.42125 (8)	0.0431 (3)
H10A	0.371536	0.437325	0.464367	0.052*
H10B	0.306043	0.396317	0.395690	0.052*
C11	0.37556 (13)	0.50125 (7)	0.36746 (8)	0.0388 (3)
H11A	0.390117	0.547983	0.394978	0.047*
H11B	0.314076	0.512110	0.327604	0.047*
C12	0.50346 (12)	0.47737 (7)	0.33020 (7)	0.0356 (3)
C13	0.57641 (13)	0.54701 (8)	0.29944 (8)	0.0433 (3)
H13A	0.595421	0.580531	0.341460	0.052*
H13B	0.657822	0.530128	0.278570	0.052*
C14	0.50566 (16)	0.59173 (8)	0.23929 (9)	0.0510 (4)
H14A	0.424038	0.608940	0.259590	0.061*
H14B	0.487752	0.558979	0.196493	0.061*
C15	0.58252 (18)	0.65952 (9)	0.21246 (11)	0.0601 (4)
H15A	0.604988	0.690289	0.255974	0.072*
H15B	0.661983	0.641748	0.189802	0.072*
C16	0.5124 (2)	0.70834 (11)	0.15573 (11)	0.0803 (6)
H16A	0.504894	0.681592	0.108633	0.120*
H16B	0.559606	0.754376	0.147875	0.120*
H16C	0.428131	0.720084	0.174612	0.120*
C17	0.58394 (13)	0.44031 (8)	0.38925 (8)	0.0413 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0285 (5)	0.0569 (6)	0.0487 (5)	0.0014 (4)	0.0003 (4)	−0.0047 (5)
N2	0.0269 (5)	0.0385 (6)	0.0409 (6)	−0.0016 (4)	0.0001 (4)	−0.0063 (4)
N3	0.0533 (8)	0.0720 (9)	0.0503 (7)	0.0081 (7)	−0.0086 (6)	−0.0002 (6)
C1	0.0304 (6)	0.0375 (6)	0.0359 (6)	0.0015 (5)	0.0029 (5)	0.0027 (5)
C2	0.0373 (7)	0.0361 (6)	0.0377 (6)	0.0003 (5)	0.0048 (5)	0.0007 (5)
C3	0.0473 (8)	0.0395 (7)	0.0506 (8)	0.0057 (6)	0.0068 (6)	0.0012 (6)
C4	0.0712 (11)	0.0392 (7)	0.0584 (9)	0.0067 (7)	0.0142 (8)	−0.0052 (7)
C5	0.0875 (13)	0.0489 (9)	0.0523 (9)	−0.0082 (8)	0.0043 (9)	−0.0148 (7)
C6	0.0600 (10)	0.0696 (11)	0.0558 (9)	−0.0041 (8)	−0.0106 (8)	−0.0160 (8)
C7	0.0430 (8)	0.0544 (8)	0.0482 (8)	0.0044 (6)	−0.0027 (6)	−0.0104 (6)
C8	0.0595 (10)	0.0813 (12)	0.0653 (11)	−0.0059 (9)	0.0233 (9)	0.0014 (9)
C9	0.0400 (8)	0.0557 (8)	0.0505 (8)	−0.0011 (6)	0.0079 (6)	−0.0062 (7)
C10	0.0412 (7)	0.0439 (7)	0.0442 (7)	0.0006 (6)	0.0068 (6)	−0.0020 (6)
C11	0.0358 (7)	0.0384 (7)	0.0422 (7)	0.0023 (5)	0.0031 (5)	−0.0042 (5)
C12	0.0314 (6)	0.0374 (6)	0.0380 (6)	−0.0012 (5)	0.0000 (5)	−0.0041 (5)
C13	0.0384 (7)	0.0405 (7)	0.0509 (8)	−0.0066 (6)	0.0051 (6)	−0.0052 (6)
C14	0.0580 (9)	0.0457 (8)	0.0491 (8)	−0.0105 (7)	0.0018 (7)	0.0016 (6)
C15	0.0675 (11)	0.0460 (8)	0.0668 (10)	−0.0092 (8)	0.0102 (9)	0.0051 (7)
C16	0.1201 (18)	0.0588 (11)	0.0620 (11)	−0.0232 (11)	−0.0118 (12)	0.0109 (9)
C17	0.0350 (7)	0.0459 (7)	0.0428 (7)	−0.0001 (6)	−0.0003 (6)	−0.0064 (6)

Geometric parameters (Å, º)

O1—C1	1.2327 (15)	C9—H9A	0.9700
N2—C1	1.3531 (16)	C9—H9B	0.9700
N2—C12	1.4691 (16)	C10—C11	1.5164 (19)
N2—H2N	0.855 (16)	C10—H10A	0.9700
N3—C17	1.1393 (19)	C10—H10B	0.9700
C1—C2	1.4946 (18)	C11—C12	1.5422 (17)
C2—C7	1.386 (2)	C11—H11A	0.9700
C2—C3	1.3894 (19)	C11—H11B	0.9700
C3—C4	1.382 (2)	C12—C17	1.4888 (19)
C3—H3	0.9300	C12—C13	1.5439 (18)
C4—C5	1.376 (3)	C13—C14	1.515 (2)
C4—H4	0.9300	C13—H13A	0.9700
C5—C6	1.377 (3)	C13—H13B	0.9700
C5—H5	0.9300	C14—C15	1.516 (2)
C6—C7	1.387 (2)	C14—H14A	0.9700
C6—H6	0.9300	C14—H14B	0.9700
C7—H7	0.9300	C15—C16	1.510 (3)
C8—C9	1.512 (2)	C15—H15A	0.9700
C8—H8A	0.9600	C15—H15B	0.9700
C8—H8B	0.9600	C16—H16A	0.9600
C8—H8C	0.9600	C16—H16B	0.9600
C9—C10	1.5191 (19)	C16—H16C	0.9600
C1—N2—C12	122.30 (11)	C9—C10—H10B	109.2
C1—N2—H2N	120.1 (10)	H10A—C10—H10B	107.9
C12—N2—H2N	117.2 (10)	C10—C11—C12	116.38 (11)
O1—C1—N2	121.18 (12)	C10—C11—H11A	108.2
O1—C1—C2	121.11 (11)	C12—C11—H11A	108.2
N2—C1—C2	117.71 (11)	C10—C11—H11B	108.2
C7—C2—C3	119.23 (13)	C12—C11—H11B	108.2
C7—C2—C1	123.33 (12)	H11A—C11—H11B	107.3
C3—C2—C1	117.41 (12)	N2—C12—C17	108.31 (10)
C4—C3—C2	120.54 (15)	N2—C12—C11	108.88 (10)
C4—C3—H3	119.7	C17—C12—C11	107.80 (11)
C2—C3—H3	119.7	N2—C12—C13	112.17 (11)
C5—C4—C3	119.85 (15)	C17—C12—C13	108.73 (11)
C5—C4—H4	120.1	C11—C12—C13	110.83 (10)
C3—C4—H4	120.1	C14—C13—C12	115.10 (11)
C4—C5—C6	120.18 (15)	C14—C13—H13A	108.5
C4—C5—H5	119.9	C12—C13—H13A	108.5
C6—C5—H5	119.9	C14—C13—H13B	108.5
C5—C6—C7	120.29 (16)	C12—C13—H13B	108.5
C5—C6—H6	119.9	H13A—C13—H13B	107.5
C7—C6—H6	119.9	C13—C14—C15	112.07 (14)
C2—C7—C6	119.91 (14)	C13—C14—H14A	109.2
C2—C7—H7	120.0	C15—C14—H14A	109.2
C6—C7—H7	120.0	C13—C14—H14B	109.2
C9—C8—H8A	109.5	C15—C14—H14B	109.2
C9—C8—H8B	109.5	H14A—C14—H14B	107.9
H8A—C8—H8B	109.5	C16—C15—C14	113.86 (16)
C9—C8—H8C	109.5	C16—C15—H15A	108.8
H8A—C8—H8C	109.5	C14—C15—H15A	108.8
H8B—C8—H8C	109.5	C16—C15—H15B	108.8
C8—C9—C10	112.28 (14)	C14—C15—H15B	108.8
C8—C9—H9A	109.1	H15A—C15—H15B	107.7
C10—C9—H9A	109.1	C15—C16—H16A	109.5
C8—C9—H9B	109.1	C15—C16—H16B	109.5
C10—C9—H9B	109.1	H16A—C16—H16B	109.5
H9A—C9—H9B	107.9	C15—C16—H16C	109.5
C11—C10—C9	112.05 (12)	H16A—C16—H16C	109.5
C11—C10—H10A	109.2	H16B—C16—H16C	109.5
C9—C10—H10A	109.2	N3—C17—C12	175.77 (15)
C11—C10—H10B	109.2
C12—N2—C1—O1	0.53 (19)	C8—C9—C10—C11	−169.86 (13)
C12—N2—C1—C2	−179.26 (11)	C9—C10—C11—C12	−174.73 (12)
O1—C1—C2—C7	−159.19 (14)	C1—N2—C12—C17	−55.56 (15)
N2—C1—C2—C7	20.60 (19)	C1—N2—C12—C11	−172.52 (11)
O1—C1—C2—C3	18.64 (18)	C1—N2—C12—C13	64.45 (15)
N2—C1—C2—C3	−161.57 (12)	C10—C11—C12—N2	75.12 (14)
C7—C2—C3—C4	−0.1 (2)	C10—C11—C12—C17	−42.17 (15)
C1—C2—C3—C4	−178.02 (13)	C10—C11—C12—C13	−161.06 (12)
C2—C3—C4—C5	−0.3 (2)	N2—C12—C13—C14	61.10 (15)
C3—C4—C5—C6	0.4 (3)	C17—C12—C13—C14	−179.14 (12)
C4—C5—C6—C7	−0.1 (3)	C11—C12—C13—C14	−60.82 (15)
C3—C2—C7—C6	0.4 (2)	C12—C13—C14—C15	179.43 (13)
C1—C2—C7—C6	178.21 (14)	C13—C14—C15—C16	−176.64 (15)
C5—C6—C7—C2	−0.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1^i	0.93	2.52	3.3046 (17)	142
N2—H2N···O1^i	0.860 (16)	2.229 (16)	3.0829 (13)	171.7 (13)

Symmetry code: (i) x−1/2, y, −z+1/2.