Crystal structure and Hirshfeld surface analysis of new polymorph of racemic 2-phenyl­butyramide

The crystal structure of new polymorph is reported in which an N—H...O hydrogen bond links mol­ecules into chains with anti­parallel (centrosymmetric) packing.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.110
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor       N1       --H1A      .     Please Check

Alert level G
PLAT793_ALERT_4_G Model has Chirality at C7          (Centro SPGR)          R Verify
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          2 Info
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         12 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 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
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: SAINT (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

2-Phenylbutyramide

Crystal data

C10H13NO	F(000) = 352
Mr = 163.21	Dx = 1.227 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.575 (2) Å	Cell parameters from 3598 reflections
b = 10.746 (3) Å	θ = 2.4–30.1°
c = 9.798 (3) Å	µ = 0.08 mm^−1
β = 101.811 (3)°	T = 100 K
V = 883.8 (4) Å^3	Block, colourless
Z = 4	0.15 × 0.1 × 0.1 mm

Data collection

Bruker APEXII CCD diffractometer	1914 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.038
Absorption correction: multi-scan (SADABS; Bruker, 2004)	θmax = 28.5°, θmin = 2.4°
Tmin = 0.674, Tmax = 0.746	h = −11→10
9961 measured reflections	k = −14→14
2240 independent reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	All H-atom parameters refined
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0614P)^2 + 0.1474P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
2240 reflections	Δρmax = 0.31 e Å^−3
161 parameters	Δρmin = −0.27 e Å^−3
0 restraints

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.

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

	x	y	z	Uiso*/Ueq
O1	0.32919 (9)	0.23775 (7)	0.06137 (7)	0.0216 (2)
N1	0.27946 (11)	0.17768 (8)	0.26886 (9)	0.0192 (2)
H1A	0.2469 (17)	0.1033 (15)	0.2342 (15)	0.031 (4)*
H1B	0.2895 (17)	0.1927 (14)	0.3601 (15)	0.028 (3)*
C1	0.68011 (12)	0.34374 (9)	0.20614 (10)	0.0179 (2)
H1	0.6296 (16)	0.3276 (12)	0.1099 (14)	0.021 (3)*
C2	0.84492 (13)	0.33963 (10)	0.24848 (11)	0.0206 (2)
H2	0.9097 (17)	0.3192 (13)	0.1809 (14)	0.027 (3)*
C3	0.91672 (13)	0.36033 (10)	0.38704 (11)	0.0217 (2)
H3	1.0322 (19)	0.3568 (14)	0.4177 (15)	0.035 (4)*
C4	0.82161 (13)	0.38440 (10)	0.48320 (11)	0.0219 (2)
H4	0.8698 (17)	0.3979 (13)	0.5822 (15)	0.027 (3)*
C5	0.65680 (13)	0.38737 (9)	0.44137 (10)	0.0184 (2)
H5	0.5908 (15)	0.4038 (12)	0.5099 (13)	0.017 (3)*
C6	0.58384 (12)	0.36770 (8)	0.30233 (10)	0.0151 (2)
C7	0.40388 (12)	0.37876 (9)	0.25694 (10)	0.0150 (2)
H7	0.3586 (15)	0.3913 (12)	0.3424 (13)	0.019 (3)*
C8	0.35882 (12)	0.49138 (9)	0.16087 (11)	0.0189 (2)
H8A	0.4084 (18)	0.5661 (13)	0.2142 (15)	0.030 (4)*
H8B	0.4098 (16)	0.4803 (12)	0.0771 (14)	0.024 (3)*
C9	0.18019 (13)	0.50974 (11)	0.11476 (12)	0.0226 (2)
H9A	0.1318 (18)	0.4394 (14)	0.0522 (15)	0.033 (4)*
H9B	0.1575 (19)	0.5862 (15)	0.0573 (16)	0.039 (4)*
H9C	0.1253 (18)	0.5153 (14)	0.1957 (16)	0.034 (4)*
C10	0.33405 (11)	0.25883 (9)	0.18573 (10)	0.0148 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0261 (4)	0.0250 (4)	0.0141 (4)	−0.0021 (3)	0.0046 (3)	−0.0035 (3)
N1	0.0241 (5)	0.0158 (4)	0.0184 (4)	−0.0028 (3)	0.0060 (3)	−0.0006 (3)
C1	0.0198 (5)	0.0181 (5)	0.0155 (4)	−0.0020 (4)	0.0026 (4)	−0.0003 (3)
C2	0.0202 (5)	0.0185 (5)	0.0244 (5)	−0.0016 (4)	0.0073 (4)	−0.0004 (4)
C3	0.0168 (5)	0.0182 (5)	0.0279 (5)	−0.0025 (4)	−0.0004 (4)	0.0011 (4)
C4	0.0259 (6)	0.0191 (5)	0.0177 (5)	−0.0025 (4)	−0.0025 (4)	−0.0003 (4)
C5	0.0227 (5)	0.0160 (5)	0.0162 (5)	−0.0006 (4)	0.0034 (4)	−0.0003 (3)
C6	0.0167 (5)	0.0118 (4)	0.0163 (4)	−0.0012 (3)	0.0022 (3)	0.0010 (3)
C7	0.0163 (5)	0.0159 (5)	0.0129 (4)	−0.0007 (3)	0.0035 (3)	−0.0002 (3)
C8	0.0187 (5)	0.0176 (5)	0.0202 (5)	−0.0003 (4)	0.0036 (4)	0.0036 (4)
C9	0.0196 (5)	0.0231 (5)	0.0244 (5)	0.0031 (4)	0.0028 (4)	0.0036 (4)
C10	0.0131 (4)	0.0158 (4)	0.0150 (4)	0.0012 (3)	0.0020 (3)	−0.0003 (3)

Geometric parameters (Å, º)

O1—C10	1.2316 (12)	C5—H5	0.979 (12)
N1—H1A	0.890 (16)	C5—C6	1.3940 (14)
N1—H1B	0.895 (15)	C6—C7	1.5206 (14)
N1—C10	1.3414 (13)	C7—H7	1.002 (12)
C1—H1	0.970 (13)	C7—C8	1.5333 (14)
C1—C2	1.3898 (15)	C7—C10	1.5282 (13)
C1—C6	1.3982 (14)	C8—H8A	1.004 (14)
C2—H2	0.973 (14)	C8—H8B	1.013 (13)
C2—C3	1.3891 (15)	C8—C9	1.5187 (15)
C3—H3	0.975 (16)	C9—H9A	1.007 (15)
C3—C4	1.3909 (16)	C9—H9B	0.992 (16)
C4—H4	0.984 (14)	C9—H9C	1.004 (15)
C4—C5	1.3890 (15)
H1A—N1—H1B	120.1 (13)	C6—C7—H7	108.0 (7)
C10—N1—H1A	118.2 (9)	C6—C7—C8	110.76 (8)
C10—N1—H1B	121.0 (9)	C6—C7—C10	110.30 (8)
C2—C1—H1	120.6 (8)	C8—C7—H7	108.4 (7)
C2—C1—C6	120.62 (9)	C10—C7—H7	108.2 (7)
C6—C1—H1	118.8 (8)	C10—C7—C8	111.06 (8)
C1—C2—H2	119.4 (8)	C7—C8—H8A	106.5 (8)
C3—C2—C1	120.46 (10)	C7—C8—H8B	107.9 (8)
C3—C2—H2	120.1 (8)	H8A—C8—H8B	108.0 (11)
C2—C3—H3	120.9 (9)	C9—C8—C7	113.41 (8)
C2—C3—C4	119.20 (10)	C9—C8—H8A	110.2 (8)
C4—C3—H3	119.9 (9)	C9—C8—H8B	110.5 (8)
C3—C4—H4	120.6 (8)	C8—C9—H9A	110.4 (8)
C5—C4—C3	120.45 (9)	C8—C9—H9B	110.2 (9)
C5—C4—H4	119.0 (8)	C8—C9—H9C	112.4 (9)
C4—C5—H5	119.9 (7)	H9A—C9—H9B	105.6 (12)
C4—C5—C6	120.73 (9)	H9A—C9—H9C	108.9 (12)
C6—C5—H5	119.4 (7)	H9B—C9—H9C	109.2 (12)
C1—C6—C7	121.41 (9)	O1—C10—N1	122.40 (9)
C5—C6—C1	118.55 (9)	O1—C10—C7	122.52 (9)
C5—C6—C7	119.98 (9)	N1—C10—C7	115.07 (8)
C1—C2—C3—C4	0.44 (16)	C5—C6—C7—C8	112.46 (10)
C1—C6—C7—C8	−64.48 (12)	C5—C6—C7—C10	−124.17 (9)
C1—C6—C7—C10	58.89 (11)	C6—C1—C2—C3	−0.55 (16)
C2—C1—C6—C5	0.03 (15)	C6—C7—C8—C9	−178.47 (8)
C2—C1—C6—C7	177.01 (9)	C6—C7—C10—O1	−83.85 (11)
C2—C3—C4—C5	0.18 (15)	C6—C7—C10—N1	95.67 (10)
C3—C4—C5—C6	−0.70 (15)	C8—C7—C10—O1	39.34 (13)
C4—C5—C6—C1	0.59 (15)	C8—C7—C10—N1	−141.14 (9)
C4—C5—C6—C7	−176.43 (9)	C10—C7—C8—C9	58.60 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1^i	0.895 (15)	2.071 (15)	2.9533 (13)	168.4 (13)

Symmetry code: (i) x, −y+1/2, z+1/2.