Ortho­rhom­bic modification of (E)-4-benzyl­idene-2-phenyl-1,3-oxazol-5(4H)-one: whole mol­ecule disorder

Ng, S.W.

doi:10.1107/S1600536809025999

organic compounds

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Volume 65| Part 8| August 2009| Page o1857

doi:10.1107/S1600536809025999

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Orthorhombic modification of (E)-4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-one: whole molecule disorder

Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 25 June 2009; accepted 4 July 2009; online 15 July 2009)

The title molecule, C₁₆H₁₁NO₂, is disordered about a pseudo-twofold rotation axis that approximately bisects the molecule along the C=O double bond. The two overlapping components are planar [r.m.s. deviation = 0.10 Å in the major 0.537 (4) component and 0.07 Å in the minor component]. The two components are aligned at 1.8 (3)°.

Related literature

For the monoclinic modification, see: Busetti et al. (1993 ).

Experimental

Crystal data

C₁₆H₁₁NO₂
M_r = 249.26
Orthorhombic, P 2₁ 2₁ 2₁
a = 3.9320 (1) Å
b = 14.7692 (5) Å
c = 20.6690 (6) Å
V = 1200.30 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 140 K
0.45 × 0.10 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
8204 measured reflections
1640 independent reflections
1312 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.125
S = 1.03
1640 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809025999/tk2490sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809025999/tk2490Isup2.hkl

checkCIF report

Related literature top

For the monoclinic modification, see: Busetti et al. (1993).

Experimental top

Anhydrous sodium acetate (0.26 g, 0.0036 mol) was added to solution of benzaldehyde (1 g, 0.0036 mol) and hippuric acid (0.77 g, 0.0043 mol) in acetic anhydride (0.27 ml, 0028 mol). The mixture was heated to 353 K for 2 h. Ethanol (10 ml) was added to the cool mixture to precipitate a yellow solid. This was collected and recrystallized from aqueous acetone to give yellow crystals in 60% yield; m.p. 443 K.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the major, 0.537 (4), component of disordered C₁₆H₁₁NO₂, shown at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Detail showing the disorder. The minor disorder component is indicated with primed atoms and dotted bonds.

(E)-4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-one top

Crystal data top

C₁₆H₁₁NO₂	F(000) = 520
M_r = 249.26	D_x = 1.379 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1737 reflections
a = 3.9320 (1) Å	θ = 2.5–25.8°
b = 14.7692 (5) Å	µ = 0.09 mm⁻¹
c = 20.6690 (6) Å	T = 140 K
V = 1200.30 (6) Å³	Prism, yellow
Z = 4	0.45 × 0.10 × 0.05 mm

Data collection top

Bruker SMART APEX diffractometer	1312 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.036
Graphite monochromator	θ_max = 27.5°, θ_min = 1.7°
ω scans	h = −5→4
8204 measured reflections	k = −19→19
1640 independent reflections	l = −25→26

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)] = 0.044	H-atom parameters constrained
wR(F²) = 0.125	w = 1/[σ²(F_o²) + (0.0752P)² + 0.1226P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
1640 reflections	Δρ_max = 0.29 e Å⁻³
182 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Absolute structure: nd
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₆H₁₁NO₂	V = 1200.30 (6) Å³
M_r = 249.26	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 3.9320 (1) Å	µ = 0.09 mm⁻¹
b = 14.7692 (5) Å	T = 140 K
c = 20.6690 (6) Å	0.45 × 0.10 × 0.05 mm

Data collection top

Bruker SMART APEX diffractometer	1312 reflections with I > 2σ(I)
8204 measured reflections	R_int = 0.036
1640 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.03	Δρ_max = 0.29 e Å⁻³
1640 reflections	Δρ_min = −0.17 e Å⁻³
182 parameters	Absolute structure: nd

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	−0.109 (5)	0.373 (3)	0.2237 (16)	0.031 (2)	0.537 (4)
O2	0.1605 (8)	0.2739 (2)	0.28782 (13)	0.0282 (5)	0.537 (4)
N1	0.432 (3)	0.3613 (3)	0.3629 (6)	0.0229 (10)	0.537 (4)
C1	0.4568 (11)	0.19591 (18)	0.37320 (16)	0.0256 (7)	0.537 (4)
C2	0.3888 (11)	0.1143 (2)	0.34231 (13)	0.0280 (10)	0.537 (4)
H2	0.2715	0.1139	0.3021	0.034*	0.537 (4)
C3	0.4924 (12)	0.03323 (18)	0.37021 (15)	0.0304 (9)	0.537 (4)
H3	0.4460	−0.0225	0.3491	0.037*	0.537 (4)
C4	0.6641 (13)	0.03378 (19)	0.42900 (16)	0.0236 (10)	0.537 (4)
H4	0.7349	−0.0216	0.4481	0.028*	0.537 (4)
C5	0.7321 (13)	0.1154 (2)	0.45989 (15)	0.0285 (11)	0.537 (4)
H5	0.8494	0.1158	0.5001	0.034*	0.537 (4)
C6	0.6284 (12)	0.19646 (18)	0.43199 (17)	0.0246 (9)	0.537 (4)
H6	0.6749	0.2522	0.4531	0.029*	0.537 (4)
C7	0.4345 (10)	0.5780 (2)	0.35423 (15)	0.0225 (7)	0.537 (4)
C8	0.4110 (11)	0.6682 (2)	0.33534 (13)	0.0264 (9)	0.537 (4)
H8	0.3029	0.6835	0.2957	0.032*	0.537 (4)
C9	0.5458 (14)	0.73583 (17)	0.37442 (17)	0.0291 (9)	0.537 (4)
H9	0.5297	0.7974	0.3615	0.035*	0.537 (4)
C10	0.7040 (15)	0.7134 (2)	0.43239 (17)	0.0333 (13)	0.537 (4)
H10	0.7960	0.7597	0.4591	0.040*	0.537 (4)
C11	0.7274 (14)	0.6233 (3)	0.45127 (17)	0.0255 (10)	0.537 (4)
H11	0.8356	0.6080	0.4909	0.031*	0.537 (4)
C12	0.5927 (12)	0.55561 (18)	0.41219 (18)	0.0270 (10)	0.537 (4)
H12	0.6088	0.4940	0.4251	0.032*	0.537 (4)
C13	0.081 (5)	0.3626 (7)	0.2675 (10)	0.0237 (18)	0.537 (4)
C14	0.2749 (12)	0.4188 (3)	0.31640 (18)	0.0247 (5)	0.537 (4)
C15	0.2789 (12)	0.5102 (3)	0.31202 (19)	0.0255 (6)	0.537 (4)
H15	0.1616	0.5341	0.2757	0.031*	0.537 (4)
C16	0.3550 (11)	0.2805 (3)	0.34289 (17)	0.0234 (6)	0.537 (4)
O1'	−0.037 (6)	0.376 (3)	0.2199 (18)	0.031 (2)	0.463
O2'	0.1691 (10)	0.4755 (2)	0.28423 (15)	0.0282 (5)	0.463
N1'	0.421 (4)	0.3896 (4)	0.3594 (7)	0.0229 (10)	0.463
C1'	0.4779 (13)	0.5543 (2)	0.36785 (19)	0.0256 (7)	0.463
C2'	0.4019 (13)	0.6351 (3)	0.33667 (16)	0.0280 (10)	0.463
H2'	0.2789	0.6345	0.2971	0.034*	0.463 (4)
C3'	0.5060 (16)	0.7170 (2)	0.3634 (2)	0.0304 (9)	0.463
H3'	0.4540	0.7723	0.3420	0.037*	0.463 (4)
C4'	0.6860 (18)	0.7179 (2)	0.4212 (2)	0.0236 (10)	0.463
H4'	0.7571	0.7738	0.4395	0.028*	0.463 (4)
C5'	0.7620 (17)	0.6370 (3)	0.4524 (2)	0.0285 (11)	0.463
H5'	0.8850	0.6377	0.4920	0.034*	0.463 (4)
C6'	0.6580 (15)	0.5552 (2)	0.4257 (2)	0.0246 (9)	0.463
H6'	0.7099	0.4999	0.4470	0.029*	0.463 (4)
C7'	0.4147 (13)	0.1731 (2)	0.35940 (18)	0.0225 (7)	0.463
C8'	0.3876 (14)	0.0824 (3)	0.34221 (15)	0.0264 (9)	0.463
H8'	0.2839	0.0660	0.3024	0.032*	0.463 (4)
C9'	0.5123 (17)	0.0157 (2)	0.38330 (19)	0.0291 (9)	0.463
H9'	0.4938	−0.0463	0.3716	0.035*	0.463 (4)
C10'	0.6641 (17)	0.0397 (3)	0.44157 (19)	0.0333 (13)	0.463
H10B	0.7493	−0.0059	0.4696	0.040*	0.463 (4)
C11'	0.6911 (16)	0.1304 (3)	0.45875 (19)	0.0255 (10)	0.463
H11B	0.7948	0.1468	0.4986	0.031*	0.463 (4)
C12'	0.5664 (15)	0.1971 (2)	0.4177 (2)	0.0270 (10)	0.463
H12B	0.5849	0.2591	0.4294	0.032*	0.463 (4)
C13'	0.112 (6)	0.3856 (9)	0.2697 (12)	0.0237 (18)	0.463
C14'	0.2695 (14)	0.3313 (3)	0.3171 (2)	0.0247 (5)	0.463
C15'	0.2625 (14)	0.2393 (3)	0.3151 (2)	0.0255 (6)	0.463
H15B	0.1408	0.2141	0.2797	0.031*	0.463 (4)
C16'	0.3654 (13)	0.4697 (3)	0.3398 (2)	0.0234 (6)	0.463

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.017 (7)	0.048 (3)	0.029 (3)	−0.004 (7)	−0.006 (5)	0.000 (2)
O2	0.0293 (11)	0.0299 (10)	0.0255 (10)	−0.0017 (12)	−0.0039 (9)	−0.0011 (10)
N1	0.0248 (13)	0.021 (3)	0.0229 (14)	0.007 (4)	0.0002 (11)	0.006 (3)
C1	0.0230 (17)	0.0248 (14)	0.0290 (17)	0.0008 (17)	0.0078 (14)	−0.0006 (12)
C2	0.0316 (18)	0.027 (3)	0.0250 (15)	−0.001 (3)	0.0010 (12)	−0.0002 (14)
C3	0.032 (2)	0.0311 (17)	0.0284 (16)	0.001 (2)	0.0008 (15)	0.0019 (14)
C4	0.027 (3)	0.0140 (17)	0.0296 (17)	−0.004 (2)	0.0084 (16)	0.0016 (13)
C5	0.030 (2)	0.0227 (18)	0.033 (3)	0.0016 (19)	0.0003 (19)	−0.0007 (14)
C6	0.0154 (19)	0.0302 (19)	0.0281 (17)	0.0010 (17)	−0.0032 (15)	−0.0020 (14)
C7	0.0216 (16)	0.0235 (15)	0.0224 (13)	0.0007 (17)	0.0047 (12)	−0.0011 (12)
C8	0.0321 (19)	0.022 (2)	0.0253 (16)	0.000 (2)	0.0020 (14)	0.0007 (14)
C9	0.035 (2)	0.0214 (13)	0.0310 (17)	−0.0025 (18)	0.0019 (16)	0.0021 (12)
C10	0.030 (3)	0.042 (3)	0.0281 (18)	0.007 (3)	−0.0007 (18)	−0.0018 (17)
C11	0.0223 (19)	0.0247 (17)	0.030 (2)	0.000 (2)	−0.0010 (17)	0.0008 (15)
C12	0.027 (2)	0.0239 (18)	0.030 (2)	0.0014 (18)	−0.0006 (17)	−0.0007 (14)
C13	0.022 (4)	0.024 (6)	0.0252 (15)	−0.009 (5)	−0.002 (2)	−0.007 (5)
C14	0.0217 (13)	0.0305 (13)	0.0217 (12)	0.0035 (16)	0.0004 (11)	−0.0006 (14)
C15	0.0237 (15)	0.0306 (14)	0.0221 (13)	0.0036 (16)	0.0002 (12)	0.0011 (15)
C16	0.0222 (14)	0.0279 (14)	0.0202 (12)	−0.0010 (17)	0.0009 (11)	−0.0006 (15)
O1'	0.017 (7)	0.048 (3)	0.029 (3)	−0.004 (7)	−0.006 (5)	0.000 (2)
O2'	0.0293 (11)	0.0299 (10)	0.0255 (10)	−0.0017 (12)	−0.0039 (9)	−0.0011 (10)
N1'	0.0248 (13)	0.021 (3)	0.0229 (14)	0.007 (4)	0.0002 (11)	0.006 (3)
C1'	0.0230 (17)	0.0248 (14)	0.0290 (17)	0.0008 (17)	0.0078 (14)	−0.0006 (12)
C2'	0.0316 (18)	0.027 (3)	0.0250 (15)	−0.001 (3)	0.0010 (12)	−0.0002 (14)
C3'	0.032 (2)	0.0311 (17)	0.0284 (16)	0.001 (2)	0.0008 (15)	0.0019 (14)
C4'	0.027 (3)	0.0140 (17)	0.0296 (17)	−0.004 (2)	0.0084 (16)	0.0016 (13)
C5'	0.030 (2)	0.0227 (18)	0.033 (3)	0.0016 (19)	0.0003 (19)	−0.0007 (14)
C6'	0.0154 (19)	0.0302 (19)	0.0281 (17)	0.0010 (17)	−0.0032 (15)	−0.0020 (14)
C7'	0.0216 (16)	0.0235 (15)	0.0224 (13)	0.0007 (17)	0.0047 (12)	−0.0011 (12)
C8'	0.0321 (19)	0.022 (2)	0.0253 (16)	0.000 (2)	0.0020 (14)	0.0007 (14)
C9'	0.035 (2)	0.0214 (13)	0.0310 (17)	−0.0025 (18)	0.0019 (16)	0.0021 (12)
C10'	0.030 (3)	0.042 (3)	0.0281 (18)	0.007 (3)	−0.0007 (18)	−0.0018 (17)
C11'	0.0223 (19)	0.0247 (17)	0.030 (2)	0.000 (2)	−0.0010 (17)	0.0008 (15)
C12'	0.027 (2)	0.0239 (18)	0.030 (2)	0.0014 (18)	−0.0006 (17)	−0.0007 (14)
C13'	0.022 (4)	0.024 (6)	0.0252 (15)	−0.009 (5)	−0.002 (2)	−0.007 (5)
C14'	0.0217 (13)	0.0305 (13)	0.0217 (12)	0.0035 (16)	0.0004 (11)	−0.0006 (14)
C15'	0.0237 (15)	0.0306 (14)	0.0221 (13)	0.0036 (16)	0.0002 (12)	0.0011 (15)
C16'	0.0222 (14)	0.0279 (14)	0.0202 (12)	−0.0010 (17)	0.0009 (11)	−0.0006 (15)

Geometric parameters (Å, º) top

O1—C13	1.18 (4)	O1'—C13'	1.19 (5)
O2—C16	1.375 (5)	O2'—C13'	1.378 (13)
O2—C13	1.412 (15)	O2'—C16'	1.386 (6)
N1—C16	1.300 (9)	N1'—C16'	1.270 (8)
N1—C14	1.424 (9)	N1'—C14'	1.365 (14)
C1—C2	1.3900	C1'—C2'	1.3900
C1—C6	1.3900	C1'—C6'	1.3900
C1—C16	1.453 (4)	C1'—C16'	1.446 (6)
C2—C3	1.3900	C2'—C3'	1.3900
C2—H2	0.9500	C2'—H2'	0.9500
C3—C4	1.3900	C3'—C4'	1.3900
C3—H3	0.9500	C3'—H3'	0.9500
C4—C5	1.3900	C4'—C5'	1.3900
C4—H4	0.9500	C4'—H4'	0.9500
C5—C6	1.3900	C5'—C6'	1.3900
C5—H5	0.9500	C5'—H5'	0.9500
C6—H6	0.9500	C6'—H6'	0.9500
C7—C8	1.3900	C7'—C8'	1.3900
C7—C12	1.3900	C7'—C12'	1.3900
C7—C15	1.463 (5)	C7'—C15'	1.467 (6)
C8—C9	1.3900	C8'—C9'	1.3900
C8—H8	0.9500	C8'—H8'	0.9500
C9—C10	1.3900	C9'—C10'	1.3900
C9—H9	0.9500	C9'—H9'	0.9500
C10—C11	1.3900	C10'—C11'	1.3900
C10—H10	0.9500	C10'—H10B	0.9500
C11—C12	1.3900	C11'—C12'	1.3900
C11—H11	0.9500	C11'—H11B	0.9500
C12—H12	0.9500	C12'—H12B	0.9500
C13—C14	1.515 (15)	C13'—C14'	1.41 (2)
C14—C15	1.352 (5)	C14'—C15'	1.359 (6)
C15—H15	0.9500	C15'—H15B	0.9500

C16—O2—C13	107.7 (8)	C13'—O2'—C16'	102.2 (11)
C16—N1—C14	103.4 (8)	C16'—N1'—C14'	107.9 (10)
C2—C1—C6	120.0	C2'—C1'—C6'	120.0
C2—C1—C16	119.6 (3)	C2'—C1'—C16'	119.4 (3)
C6—C1—C16	120.4 (3)	C6'—C1'—C16'	120.6 (3)
C3—C2—C1	120.0	C3'—C2'—C1'	120.0
C3—C2—H2	120.0	C3'—C2'—H2'	120.0
C1—C2—H2	120.0	C1'—C2'—H2'	120.0
C2—C3—C4	120.0	C2'—C3'—C4'	120.0
C2—C3—H3	120.0	C2'—C3'—H3'	120.0
C4—C3—H3	120.0	C4'—C3'—H3'	120.0
C5—C4—C3	120.0	C5'—C4'—C3'	120.0
C5—C4—H4	120.0	C5'—C4'—H4'	120.0
C3—C4—H4	120.0	C3'—C4'—H4'	120.0
C6—C5—C4	120.0	C4'—C5'—C6'	120.0
C6—C5—H5	120.0	C4'—C5'—H5'	120.0
C4—C5—H5	120.0	C6'—C5'—H5'	120.0
C5—C6—C1	120.0	C5'—C6'—C1'	120.0
C5—C6—H6	120.0	C5'—C6'—H6'	120.0
C1—C6—H6	120.0	C1'—C6'—H6'	120.0
C8—C7—C12	120.0	C8'—C7'—C12'	120.0
C8—C7—C15	117.4 (3)	C8'—C7'—C15'	116.8 (4)
C12—C7—C15	122.5 (3)	C12'—C7'—C15'	123.1 (4)
C9—C8—C7	120.0	C7'—C8'—C9'	120.0
C9—C8—H8	120.0	C7'—C8'—H8'	120.0
C7—C8—H8	120.0	C9'—C8'—H8'	120.0
C8—C9—C10	120.0	C8'—C9'—C10'	120.0
C8—C9—H9	120.0	C8'—C9'—H9'	120.0
C10—C9—H9	120.0	C10'—C9'—H9'	120.0
C11—C10—C9	120.0	C11'—C10'—C9'	120.0
C11—C10—H10	120.0	C11'—C10'—H10B	120.0
C9—C10—H10	120.0	C9'—C10'—H10B	120.0
C10—C11—C12	120.0	C10'—C11'—C12'	120.0
C10—C11—H11	120.0	C10'—C11'—H11B	120.0
C12—C11—H11	120.0	C12'—C11'—H11B	120.0
C11—C12—C7	120.0	C11'—C12'—C7'	120.0
C11—C12—H12	120.0	C11'—C12'—H12B	120.0
C7—C12—H12	120.0	C7'—C12'—H12B	120.0
O1—C13—O2	119 (2)	O1'—C13'—O2'	113 (3)
O1—C13—C14	140 (2)	O1'—C13'—C14'	138 (3)
O2—C13—C14	101.4 (13)	O2'—C13'—C14'	109.0 (15)
C15—C14—N1	129.4 (5)	C15'—C14'—N1'	131.3 (6)
C15—C14—C13	120.5 (7)	C15'—C14'—C13'	122.6 (7)
N1—C14—C13	110.1 (8)	N1'—C14'—C13'	106.1 (7)
C14—C15—C7	130.4 (4)	C14'—C15'—C7'	129.7 (5)
C14—C15—H15	114.8	C14'—C15'—H15B	115.2
C7—C15—H15	114.8	C7'—C15'—H15B	115.2
N1—C16—O2	117.3 (6)	N1'—C16'—O2'	114.7 (8)
N1—C16—C1	126.0 (6)	N1'—C16'—C1'	128.5 (8)
O2—C16—C1	116.7 (4)	O2'—C16'—C1'	116.7 (4)

C6—C1—C2—C3	0.0	C6'—C1'—C2'—C3'	0.0
C16—C1—C2—C3	178.5 (4)	C16'—C1'—C2'—C3'	179.5 (5)
C1—C2—C3—C4	0.0	C1'—C2'—C3'—C4'	0.0
C2—C3—C4—C5	0.0	C2'—C3'—C4'—C5'	0.0
C3—C4—C5—C6	0.0	C3'—C4'—C5'—C6'	0.0
C4—C5—C6—C1	0.0	C4'—C5'—C6'—C1'	0.0
C2—C1—C6—C5	0.0	C2'—C1'—C6'—C5'	0.0
C16—C1—C6—C5	−178.5 (4)	C16'—C1'—C6'—C5'	−179.5 (5)
C12—C7—C8—C9	0.0	C12'—C7'—C8'—C9'	0.0
C15—C7—C8—C9	178.2 (4)	C15'—C7'—C8'—C9'	−177.1 (5)
C7—C8—C9—C10	0.0	C7'—C8'—C9'—C10'	0.0
C8—C9—C10—C11	0.0	C8'—C9'—C10'—C11'	0.0
C9—C10—C11—C12	0.0	C9'—C10'—C11'—C12'	0.0
C10—C11—C12—C7	0.0	C10'—C11'—C12'—C7'	0.0
C8—C7—C12—C11	0.0	C8'—C7'—C12'—C11'	0.0
C15—C7—C12—C11	−178.1 (4)	C15'—C7'—C12'—C11'	176.9 (5)
C16—O2—C13—O1	−173.9 (18)	C16'—O2'—C13'—O1'	−175 (2)
C16—O2—C13—C14	3.3 (13)	C16'—O2'—C13'—C14'	1.1 (18)
C16—N1—C14—C15	−178.0 (5)	C16'—N1'—C14'—C15'	177.7 (7)
C16—N1—C14—C13	2.4 (13)	C16'—N1'—C14'—C13'	−0.4 (16)
O1—C13—C14—C15	−7 (3)	O1'—C13'—C14'—C15'	−4 (4)
O2—C13—C14—C15	176.8 (7)	O2'—C13'—C14'—C15'	−178.8 (9)
O1—C13—C14—N1	173 (3)	O1'—C13'—C14'—N1'	175 (3)
O2—C13—C14—N1	−3.6 (15)	O2'—C13'—C14'—N1'	−1 (2)
N1—C14—C15—C7	−2.2 (10)	N1'—C14'—C15'—C7'	1.2 (13)
C13—C14—C15—C7	177.3 (10)	C13'—C14'—C15'—C7'	179.0 (13)
C8—C7—C15—C14	176.7 (4)	C8'—C7'—C15'—C14'	−175.1 (5)
C12—C7—C15—C14	−5.2 (6)	C12'—C7'—C15'—C14'	7.9 (8)
C14—N1—C16—O2	−0.2 (11)	C14'—N1'—C16'—O2'	1.2 (14)
C14—N1—C16—C1	179.5 (5)	C14'—N1'—C16'—C1'	−179.1 (6)
C13—O2—C16—N1	−2.2 (12)	C13'—O2'—C16'—N1'	−1.4 (15)
C13—O2—C16—C1	178.1 (10)	C13'—O2'—C16'—C1'	178.8 (12)
C2—C1—C16—N1	−172.6 (8)	C2'—C1'—C16'—N1'	176.8 (10)
C6—C1—C16—N1	5.9 (9)	C6'—C1'—C16'—N1'	−3.7 (11)
C2—C1—C16—O2	7.1 (5)	C2'—C1'—C16'—O2'	−3.5 (6)
C6—C1—C16—O2	−174.4 (3)	C6'—C1'—C16'—O2'	176.0 (4)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₁NO₂
M_r	249.26
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	140
a, b, c (Å)	3.9320 (1), 14.7692 (5), 20.6690 (6)
V (Å³)	1200.30 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.45 × 0.10 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8204, 1640, 1312
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.125, 1.03
No. of reflections	1640
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.17
Absolute structure	Nd

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

I thank Professor Abdullah Mohamed Asiri of King Abdul Aziz University for providing the crystal for this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Busetti, V., Mayoral, J. A., Cativiela, C., de Villegas, M. D. & Ajo, D. (1993). Z. Kristallogr. 203, 49–55. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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