Ethyl N-(2-benzoyl-3-oxo-3-phenyl­propano­yl)carbamate

Akkurt, M.; Sarıoğlu, A.O.; Sönmez, M.; Tahir, M.N.

doi:10.1107/S1600536813000445

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o220

doi:10.1107/S1600536813000445

Open

access

Ethyl N-(2-benzoyl-3-oxo-3-phenylpropanoyl)carbamate

Mehmet Akkurt,^a ^* Ahmet Oral Sarıoğlu,^b Mehmet Sönmez ^b and Muhammad Nawaz Tahir ^c ^*

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Chemistry, Faculty of Arts and Sciences, Gaziantep University, 27310 Şehitkamil–Gaziantep, Turkey, and ^cDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: akkurt@erciyes.edu.tr, dmntahir_uos@yahoo.com

(Received 4 January 2013; accepted 5 January 2013; online 12 January 2013)

In the title compound, C₁₉H₁₇NO₅, the dihedral angle between the phenyl groups is 79.55 (15)°. The terminal ethoxy group is disordered over two orientations in a 0.873 (6):0.127 (6) ratio. In the crystal, molecules are linked by N—H⋯O and C—H⋯O hydrogen bonds into [001] chains which incorporate R₁²(6) loops. A very weak C—H⋯π contact also occurs.

Related literature

For background to the carboxamide [–C(O)NH–] group, see: Sönmez (2001 ). For further synthetic details, see: Fabian et al. (1992 ).

Experimental

Crystal data

C₁₉H₁₇NO₅
M_r = 339.34
Monoclinic, C 2/c
a = 33.088 (8) Å
b = 12.732 (3) Å
c = 8.7110 (18) Å
β = 97.896 (9)°
V = 3635.0 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.35 × 0.18 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.981, T_max = 0.986
14531 measured reflections
3579 independent reflections
1910 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.132
S = 1.01
3579 reflections
234 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C10–C15 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3ⁱ	0.86	2.37	3.025 (2)	133
N1—H1⋯O4ⁱ	0.86	2.08	2.842 (2)	147
C8—H8⋯O3ⁱ	0.98	2.38	3.263 (3)	150
C19B—H19F⋯Cg2ⁱⁱ	0.96	2.96	3.786 (5)	145
Symmetry codes: (i) $[x, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+1, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813000445/hb7023sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813000445/hb7023Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813000445/hb7023Isup3.cml

checkCIF report

Comment top

The carboxamide [–C(O)NH–] group, which seems to be everywhere throughout nature in the primary structure of proteins, is an important ligand construction unit for coordination chemists (Sönmez, 2001). The high stability of the amide linkage toward hydrolysis is of crucial importance to biological systems, since it allows the construction of peptides from relatively simple amino acid precursors.

In the title compound (I), (Fig. 1), the C1–C6 and C10–C15 phenyl rings make a dihedral angle of 79.55 (15)° with each other. The C7–C8–C16–O3, C8–C16–N1–C17, O3–C16–N1–C17, C16–N1–C17–O4 and C16–N1–C17–O5 torsion angles are -23.0 (3), -176.6 (2), 3.9 (4), 2.6 (4) and -177.2 (2)°, respectively.

In the crystal structure, N—H···O and C—H···O hydrogen bonds (Table 1, Fig. 2) connect the neighbouring molecules, into chains running along the c axis, forming the R²₁(6) motifs (Fig. 2). Furthermore, C—H···π interactions between the H19F hydrogen atom of the methyl group and the C10–C15 phenyl ring (with centroid Cg2) is also observed (Table 1).

Related literature top

For background to the carboxamide [–C(O)NH–] group, see: Sönmez (2001). For further synthetic details, see: Fabian et al. (1992).

Experimental top

Dibenzoylaceticacid-N-carboxyethylamide was prepared from reaction of 4-benzoyl-5-phenyl-2,3-furandione and ethyl urethane as the method reported earlier (Fabian et al., 1992). These compounds were refluxed in benzene for 5 h. The solvent was evaporated under reduced pressure to give an oily residue which was treated with ether and finally crystallized from absolute ethanol as colourless needles. Analysis calculated for (C₁₉H₁₇NO₅): C 67.25, H 5.01, N 4.14. Found: C 67.22, H 5.06, N 4.30.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids for non-H atoms drawn at the 30% probability level. Only the major disorder component is shown.
	Fig. 2. The packing and hydrogen bonding of the title compound, viewing along the b axis. H atoms not involved in hydrogen bonding and the minor disordered component are omitted for clarity.

Ethyl N-(2-benzoyl-3-oxo-3-phenylpropanoyl)carbamate top

Crystal data top

C₁₉H₁₇NO₅	F(000) = 1424
M_r = 339.34	D_x = 1.240 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 270 reflections
a = 33.088 (8) Å	θ = 3.1–21.4°
b = 12.732 (3) Å	µ = 0.09 mm⁻¹
c = 8.7110 (18) Å	T = 296 K
β = 97.896 (9)°	Needle, white
V = 3635.0 (14) Å³	0.35 × 0.18 × 0.16 mm
Z = 8

Data collection top

Bruker Kappa APEXII CCD diffractometer	3579 independent reflections
Radiation source: fine-focus sealed tube	1910 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ω scans	θ_max = 26.0°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −37→40
T_min = 0.981, T_max = 0.986	k = −15→15
14531 measured reflections	l = −8→10

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.132	w = 1/[σ²(F_o²) + (0.0486P)² + 0.910P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
3579 reflections	Δρ_max = 0.16 e Å⁻³
234 parameters	Δρ_min = −0.13 e Å⁻³
4 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), FC^*=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0030 (4)

Crystal data top

C₁₉H₁₇NO₅	V = 3635.0 (14) Å³
M_r = 339.34	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 33.088 (8) Å	µ = 0.09 mm⁻¹
b = 12.732 (3) Å	T = 296 K
c = 8.7110 (18) Å	0.35 × 0.18 × 0.16 mm
β = 97.896 (9)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3579 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1910 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.986	R_int = 0.050
14531 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	4 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.01	Δρ_max = 0.16 e Å⁻³
3579 reflections	Δρ_min = −0.13 e Å⁻³
234 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.18768 (6)	0.74420 (16)	0.0969 (2)	0.0913 (9)
O2	0.09155 (6)	0.76202 (14)	0.08336 (19)	0.0757 (8)
O3	0.12375 (5)	0.56205 (12)	−0.09053 (15)	0.0564 (6)
O4	0.05773 (5)	0.42206 (13)	−0.13912 (16)	0.0578 (6)
O5	0.03265 (5)	0.39586 (14)	0.08394 (17)	0.0693 (7)
N1	0.08534 (6)	0.50073 (15)	0.08736 (18)	0.0494 (7)
C1	0.21155 (8)	0.5710 (2)	0.1313 (2)	0.0558 (10)
C2	0.24785 (9)	0.5949 (3)	0.0759 (3)	0.0819 (12)
C3	0.27677 (11)	0.5189 (4)	0.0679 (4)	0.1085 (18)
C4	0.27046 (12)	0.4194 (3)	0.1159 (4)	0.1102 (17)
C5	0.23524 (12)	0.3949 (3)	0.1725 (4)	0.0984 (17)
C6	0.20565 (9)	0.4704 (2)	0.1804 (3)	0.0707 (11)
C7	0.18068 (8)	0.6541 (2)	0.1304 (3)	0.0553 (10)
C8	0.13836 (7)	0.62652 (16)	0.1695 (2)	0.0435 (8)
C9	0.11479 (8)	0.72705 (18)	0.1908 (3)	0.0511 (9)
C10	0.12157 (8)	0.78140 (18)	0.3436 (3)	0.0520 (9)
C11	0.14062 (9)	0.7351 (2)	0.4765 (3)	0.0754 (11)
C12	0.14478 (11)	0.7874 (3)	0.6156 (3)	0.1070 (18)
C13	0.13103 (12)	0.8877 (3)	0.6216 (4)	0.1085 (18)
C14	0.11213 (11)	0.9365 (2)	0.4910 (4)	0.0946 (14)
C15	0.10659 (9)	0.8823 (2)	0.3516 (3)	0.0717 (11)
C16	0.11539 (7)	0.56060 (17)	0.0400 (2)	0.0444 (8)
C17	0.05827 (7)	0.43737 (18)	−0.0035 (2)	0.0475 (8)
C18B	−0.00031 (11)	0.3297 (3)	0.0107 (4)	0.0681 (16)	0.874 (6)
C19B	0.01476 (14)	0.2202 (3)	0.0081 (6)	0.122 (2)	0.874 (6)
C19A	−0.0059 (10)	0.230 (2)	0.104 (4)	0.122 (2)	0.127 (6)
C18A	0.0143 (10)	0.302 (2)	−0.003 (3)	0.0681 (16)	0.127 (6)
H2	0.25255	0.66297	0.04389	0.0984*
H1	0.08306	0.50283	0.18448	0.0593*
H5	0.23111	0.32685	0.20608	0.1180*
H6	0.18166	0.45305	0.21893	0.0846*
H8	0.14126	0.58613	0.26611	0.0522*
H11	0.15087	0.66726	0.47217	0.0903*
H12	0.15696	0.75432	0.70541	0.1281*
H13	0.13449	0.92367	0.71546	0.1301*
H14	0.10307	1.00540	0.49576	0.1135*
H15	0.09279	0.91396	0.26339	0.0861*
H18C	−0.00918	0.35382	−0.09419	0.0818*	0.874 (6)
H18D	−0.02337	0.33326	0.06829	0.0818*	0.874 (6)
H19D	−0.00633	0.17611	−0.04401	0.1830*	0.874 (6)
H19E	0.02221	0.19582	0.11238	0.1830*	0.874 (6)
H19F	0.03817	0.21784	−0.04587	0.1830*	0.874 (6)
H3	0.30085	0.53546	0.02943	0.1298*
H4	0.29018	0.36801	0.11008	0.1319*
H18A	0.03551	0.26331	−0.04608	0.0818*	0.127 (6)
H18B	−0.00573	0.32448	−0.08842	0.0818*	0.127 (6)
H19A	−0.02677	0.18932	0.04337	0.1830*	0.127 (6)
H19B	−0.01783	0.27177	0.17740	0.1830*	0.127 (6)
H19C	0.01418	0.18378	0.15742	0.1830*	0.127 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0800 (16)	0.0636 (13)	0.1396 (18)	−0.0162 (11)	0.0482 (13)	−0.0004 (12)
O2	0.0850 (15)	0.0718 (13)	0.0665 (12)	0.0153 (10)	−0.0035 (10)	−0.0004 (9)
O3	0.0666 (12)	0.0714 (11)	0.0345 (8)	−0.0136 (9)	0.0190 (7)	−0.0040 (7)
O4	0.0639 (12)	0.0765 (12)	0.0335 (9)	−0.0142 (9)	0.0081 (7)	−0.0070 (7)
O5	0.0696 (13)	0.0926 (13)	0.0477 (9)	−0.0354 (10)	0.0153 (8)	0.0001 (8)
N1	0.0573 (14)	0.0659 (13)	0.0265 (9)	−0.0173 (10)	0.0107 (8)	−0.0042 (8)
C1	0.0473 (18)	0.0715 (19)	0.0478 (14)	−0.0040 (14)	0.0034 (11)	−0.0022 (12)
C2	0.056 (2)	0.095 (2)	0.097 (2)	0.0000 (18)	0.0189 (16)	0.0082 (17)
C3	0.059 (2)	0.146 (4)	0.125 (3)	0.022 (2)	0.029 (2)	0.017 (3)
C4	0.077 (3)	0.127 (3)	0.127 (3)	0.045 (2)	0.015 (2)	0.017 (2)
C5	0.083 (3)	0.097 (3)	0.115 (3)	0.028 (2)	0.013 (2)	0.026 (2)
C6	0.058 (2)	0.081 (2)	0.0727 (18)	0.0107 (16)	0.0079 (13)	0.0116 (15)
C7	0.0559 (19)	0.0575 (16)	0.0534 (14)	−0.0127 (14)	0.0111 (12)	−0.0060 (12)
C8	0.0475 (16)	0.0496 (14)	0.0339 (11)	−0.0052 (11)	0.0075 (9)	−0.0025 (9)
C9	0.0540 (18)	0.0521 (15)	0.0488 (14)	−0.0059 (12)	0.0131 (12)	0.0011 (11)
C10	0.0574 (17)	0.0474 (15)	0.0547 (14)	−0.0077 (12)	0.0205 (12)	−0.0095 (11)
C11	0.096 (2)	0.0686 (18)	0.0586 (17)	0.0088 (16)	0.0003 (15)	−0.0192 (14)
C12	0.149 (4)	0.102 (3)	0.065 (2)	0.027 (2)	−0.0033 (19)	−0.0311 (18)
C13	0.142 (4)	0.104 (3)	0.079 (2)	0.011 (2)	0.013 (2)	−0.041 (2)
C14	0.129 (3)	0.064 (2)	0.098 (2)	0.0025 (19)	0.041 (2)	−0.0261 (18)
C15	0.091 (2)	0.0568 (18)	0.0722 (18)	−0.0022 (15)	0.0287 (15)	−0.0056 (13)
C16	0.0494 (16)	0.0486 (14)	0.0363 (12)	−0.0022 (11)	0.0102 (10)	0.0017 (10)
C17	0.0522 (17)	0.0552 (14)	0.0357 (12)	−0.0056 (12)	0.0080 (10)	0.0028 (10)
C18B	0.050 (3)	0.079 (3)	0.076 (2)	−0.020 (2)	0.0109 (19)	−0.0027 (16)
C19B	0.079 (3)	0.079 (3)	0.211 (6)	−0.007 (2)	0.032 (3)	−0.025 (3)
C19A	0.079 (3)	0.079 (3)	0.211 (6)	−0.007 (2)	0.032 (3)	−0.025 (3)
C18A	0.050 (3)	0.079 (3)	0.076 (2)	−0.020 (2)	0.0109 (19)	−0.0027 (16)

Geometric parameters (Å, º) top

O1—C7	1.214 (3)	C13—C14	1.370 (5)
O2—C9	1.212 (3)	C14—C15	1.387 (4)
O3—C16	1.207 (2)	C18A—C19A	1.53 (4)
O4—C17	1.195 (2)	C18B—C19B	1.482 (5)
O5—C17	1.325 (3)	C2—H2	0.9300
O5—C18B	1.454 (4)	C3—H3	0.9300
O5—C18A	1.50 (3)	C4—H4	0.9300
N1—C16	1.361 (3)	C5—H5	0.9300
N1—C17	1.373 (3)	C6—H6	0.9300
N1—H1	0.8600	C8—H8	0.9800
C1—C2	1.388 (4)	C11—H11	0.9300
C1—C7	1.470 (4)	C12—H12	0.9300
C1—C6	1.373 (4)	C13—H13	0.9300
C2—C3	1.369 (6)	C14—H14	0.9300
C3—C4	1.359 (6)	C15—H15	0.9300
C4—C5	1.363 (6)	C18A—H18B	0.9700
C5—C6	1.381 (5)	C18A—H18A	0.9700
C7—C8	1.527 (4)	C18B—H18D	0.9700
C8—C9	1.523 (3)	C18B—H18C	0.9700
C8—C16	1.523 (3)	C19A—H19A	0.9600
C9—C10	1.490 (4)	C19A—H19C	0.9600
C10—C11	1.373 (4)	C19A—H19B	0.9600
C10—C15	1.382 (4)	C19B—H19E	0.9600
C11—C12	1.373 (4)	C19B—H19F	0.9600
C12—C13	1.359 (5)	C19B—H19D	0.9600

C17—O5—C18B	118.64 (19)	C3—C4—H4	120.00
C17—O5—C18A	105.9 (11)	C5—C4—H4	120.00
C16—N1—C17	126.89 (16)	C4—C5—H5	120.00
C17—N1—H1	117.00	C6—C5—H5	120.00
C16—N1—H1	117.00	C1—C6—H6	120.00
C2—C1—C7	118.3 (3)	C5—C6—H6	120.00
C2—C1—C6	118.7 (3)	C7—C8—H8	109.00
C6—C1—C7	123.0 (2)	C9—C8—H8	109.00
C1—C2—C3	120.5 (3)	C16—C8—H8	109.00
C2—C3—C4	120.3 (3)	C10—C11—H11	119.00
C3—C4—C5	120.0 (4)	C12—C11—H11	120.00
C4—C5—C6	120.4 (3)	C11—C12—H12	120.00
C1—C6—C5	120.1 (3)	C13—C12—H12	120.00
C1—C7—C8	119.4 (2)	C12—C13—H13	120.00
O1—C7—C1	121.8 (2)	C14—C13—H13	120.00
O1—C7—C8	118.8 (2)	C13—C14—H14	120.00
C9—C8—C16	109.97 (19)	C15—C14—H14	120.00
C7—C8—C9	109.54 (19)	C10—C15—H15	120.00
C7—C8—C16	109.95 (17)	C14—C15—H15	120.00
O2—C9—C8	119.7 (2)	H18A—C18A—H18B	108.00
O2—C9—C10	121.4 (2)	O5—C18A—H18A	110.00
C8—C9—C10	118.8 (2)	O5—C18A—H18B	110.00
C9—C10—C11	123.3 (2)	C19A—C18A—H18A	109.00
C11—C10—C15	118.9 (2)	C19A—C18A—H18B	110.00
C9—C10—C15	117.8 (2)	C19B—C18B—H18C	110.00
C10—C11—C12	121.0 (3)	C19B—C18B—H18D	110.00
C11—C12—C13	119.8 (3)	O5—C18B—H18D	110.00
C12—C13—C14	120.8 (3)	O5—C18B—H18C	110.00
C13—C14—C15	119.5 (3)	H18C—C18B—H18D	108.00
C10—C15—C14	120.1 (3)	C18A—C19A—H19A	109.00
O3—C16—N1	124.45 (19)	C18A—C19A—H19B	109.00
N1—C16—C8	113.28 (16)	H19A—C19A—H19C	109.00
O3—C16—C8	122.3 (2)	H19B—C19A—H19C	110.00
O4—C17—N1	125.9 (2)	C18A—C19A—H19C	109.00
O4—C17—O5	125.4 (2)	H19A—C19A—H19B	110.00
O5—C17—N1	108.74 (16)	C18B—C19B—H19F	109.00
O5—C18A—C19A	111 (2)	H19E—C19B—H19F	109.00
O5—C18B—C19B	108.5 (3)	H19D—C19B—H19E	110.00
C1—C2—H2	120.00	H19D—C19B—H19F	109.00
C3—C2—H2	120.00	C18B—C19B—H19D	109.00
C2—C3—H3	120.00	C18B—C19B—H19E	109.00
C4—C3—H3	120.00

C18B—O5—C17—O4	−3.0 (4)	C1—C7—C8—C16	−69.7 (3)
C18B—O5—C17—N1	176.9 (2)	C7—C8—C9—O2	95.7 (3)
C17—O5—C18B—C19B	88.0 (3)	C7—C8—C9—C10	−83.1 (3)
C16—N1—C17—O4	2.7 (4)	C16—C8—C9—O2	−25.2 (3)
C16—N1—C17—O5	−177.2 (2)	C16—C8—C9—C10	156.0 (2)
C17—N1—C16—O3	−3.9 (4)	C7—C8—C16—O3	−23.0 (3)
C17—N1—C16—C8	176.6 (2)	C9—C8—C16—N1	−82.8 (2)
C6—C1—C2—C3	1.2 (4)	C7—C8—C16—N1	156.55 (19)
C7—C1—C2—C3	−177.1 (3)	C9—C8—C16—O3	97.7 (3)
C2—C1—C6—C5	−0.8 (4)	C8—C9—C10—C15	167.1 (2)
C7—C1—C6—C5	177.4 (3)	O2—C9—C10—C11	166.1 (3)
C2—C1—C7—O1	−7.1 (4)	O2—C9—C10—C15	−11.7 (4)
C6—C1—C7—O1	174.7 (2)	C8—C9—C10—C11	−15.1 (4)
C6—C1—C7—C8	−6.5 (3)	C9—C10—C11—C12	−177.6 (3)
C2—C1—C7—C8	171.7 (2)	C15—C10—C11—C12	0.2 (4)
C1—C2—C3—C4	−0.8 (5)	C9—C10—C15—C14	−179.9 (3)
C2—C3—C4—C5	−0.1 (5)	C11—C10—C15—C14	2.2 (4)
C3—C4—C5—C6	0.5 (5)	C10—C11—C12—C13	−2.1 (5)
C4—C5—C6—C1	−0.1 (5)	C11—C12—C13—C14	1.6 (6)
O1—C7—C8—C16	109.2 (2)	C12—C13—C14—C15	0.8 (6)
O1—C7—C8—C9	−11.8 (3)	C13—C14—C15—C10	−2.7 (5)
C1—C7—C8—C9	169.4 (2)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C10–C15 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.86	2.37	3.025 (2)	133
N1—H1···O4ⁱ	0.86	2.08	2.842 (2)	147
C8—H8···O3ⁱ	0.98	2.38	3.263 (3)	150
C19B—H19F···Cg2ⁱⁱ	0.96	2.96	3.786 (5)	145

Symmetry codes: (i) x, −y+1, z+1/2; (ii) x, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₇NO₅
M_r	339.34
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	33.088 (8), 12.732 (3), 8.7110 (18)
β (°)	97.896 (9)
V (Å³)	3635.0 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.35 × 0.18 × 0.16

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.981, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	14531, 3579, 1910
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.132, 1.01
No. of reflections	3579
No. of parameters	234
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.13

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and PLATON (Spek, 2009), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C10–C15 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.86	2.37	3.025 (2)	133
N1—H1···O4ⁱ	0.86	2.08	2.842 (2)	147
C8—H8···O3ⁱ	0.98	2.38	3.263 (3)	150
C19B—H19F···Cg2ⁱⁱ	0.96	2.96	3.786 (5)	145

Symmetry codes: (i) x, −y+1, z+1/2; (ii) x, −y+1, z−1/2.

Acknowledgements

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fabian, W. F., Kollenz, G., Akcamur, Y., Kök, T. R., Tezcan, M., Akkurt, M. & Hiller, W. (1992). Monatsch. Chem. 123, 265–275. CrossRef CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sönmez, M. (2001). Turk. J. Chem. 25, 181–185. Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o220

doi:10.1107/S1600536813000445

Open

access