4-Chloro-N-[(E)-(3,4-dimeth­oxy­phen­yl)methyl­idene]aniline

Tahir, M.N.; Tariq, M.I.; Sarfraz, M.; Ahmad, S.; Tariq, R.H.

doi:10.1107/S1600536810032782

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page o2355

https://doi.org/10.1107/S1600536810032782

Open

access

4-Chloro-N-[(E)-(3,4-dimethoxyphenyl)methylidene]aniline

M. Nawaz Tahir,^a ^* Muhammad Ilyas Tariq,^b Muhammad Sarfraz,^b Shahbaz Ahmad ^b and Riaz H. Tariq ^c

^aDepartment of Physics, University of Sargodha, Sargodha, Pakistan, ^bDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan, and ^cInstitute of Chemical and Pharmaceutical Sciences, The University of Faisalabad, Faisalabad, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 14 August 2010; accepted 15 August 2010; online 18 August 2010)

The asymmetric unit of the title compound, C₁₅H₁₄ClNO₂, contains two molecules with significantly different conformations: the dihedral angles between the 4-chloroaniline and 3,4-dimethoxyphenyl (excluding C atoms) moieties are 19.68 (7) and 45.54 (4)°. In the crystal, the molecules are linked by C—H⋯O hydrogen bonds and weak C—H⋯π interactions.

Related literature

For related structures, see: Dehno Khalaji et al. (2009 ); Shang & Tan (2007 ).

Experimental

Crystal data

C₁₅H₁₄ClNO₂
M_r = 275.72
Monoclinic, P 2₁ /c
a = 12.4227 (4) Å
b = 7.3638 (2) Å
c = 30.4583 (13) Å
β = 96.080 (2)°
V = 2770.60 (17) Å³
Z = 8
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 296 K
0.35 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.932, T_max = 0.950
20975 measured reflections
5007 independent reflections
3456 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.120
S = 1.05
5007 reflections
347 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C8–C13 and C16–C21 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14B⋯O3ⁱ	0.96	2.52	3.468 (3)	170
C6—H6⋯Cg3ⁱⁱ	0.93	2.85	3.602 (2)	139
C18—H18⋯Cg1	0.93	2.89	3.588 (2)	133
C21—H21⋯Cg3ⁱⁱⁱ	0.93	2.88	3.549 (2)	130
C29—H29C⋯Cg2	0.96	2.88	3.782 (2)	157
C30—H30C⋯Cg1^iv	0.96	2.76	3.613 (2)	148
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x, y+1, z; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) x+1, y-1, z.

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 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810032782/hb5610sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810032782/hb5610Isup2.hkl

checkCIF report

Comment top

The crystal structures of (II) i.e, 4-chloro-N-(3,4,5-trimethoxybenzylidene)aniline (Dehno Khalaji et al., 2009) and (III) i.e, 4-[(4-chlorophenyl)iminomethyl]-2-methoxyphenol (Shang & Tan, 2007) have been published which are related to the title compound (I, Fig. 1)

The title compound consists of two molecules in the crystallographic asymmetric unit which differ from each other geometrically. In one molecule, the 4-chloroanilinic group A (C1—C6/N1/CL1) and group B (C7—C13/O1/O2) of 3,4-dimethoxyphenyl are planar with r.m.s. deviation of 0.0081 and 0.0146 Å, respectively. The dihedral angle between A/B is 45.54 (4)°. The C-atoms C14 and C15 of 3,4-dimethoxyphenyl are at a distance of -0.0058 (35) and 0.1132 (34) Å, respectively from the parent group B. In the second molecule, the 4-chloroanilinic group C (C16—C21/N2/CL2) and group D (C22—C28/O3/O4) of 3,4-dimethoxyphenyl are planar with r.m.s. deviation of 0.0094 and 0.0063 Å, respectively. The dihedral angle between C/D is 19.68 (7)°. The C-atoms C29 and C30 of 3,4-dimethoxyphenyl are at a distance of -0.2256 (33) and -0.2205 (31) Å, respectively from the parent group D. This shows that both molecules differ at large from each other. The molecules are stabilized through C—H···O type of H-bonding and π···π interactions (Table 1).

Related literature top

For related structures, see: Dehno Khalaji et al. (2009); Shang & Tan (2007).

Experimental top

Equimolar quantities of 4-chloroaniline and 3,4-dimethoxybenzaldehyde were refluxed in methanol for 30 min. The solution was kept at room temperature which afforded orange light yellow prisms of (I) after 48 h.

Structure description top

For related structures, see: Dehno Khalaji et al. (2009); Shang & Tan (2007).

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 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

Fig. 1. View of (I) with displacement ellipsoids drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii.

4-Chloro-N-[(E)-(3,4-dimethoxyphenyl)methylidene]aniline top

Crystal data top

C₁₅H₁₄ClNO₂	F(000) = 1152
M_r = 275.72	D_x = 1.322 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3456 reflections
a = 12.4227 (4) Å	θ = 1.7–25.3°
b = 7.3638 (2) Å	µ = 0.27 mm⁻¹
c = 30.4583 (13) Å	T = 296 K
β = 96.080 (2)°	Prism, light yellow
V = 2770.60 (17) Å³	0.35 × 0.22 × 0.20 mm
Z = 8

Data collection top

Bruker Kappa APEXII CCD diffractometer	5007 independent reflections
Radiation source: fine-focus sealed tube	3456 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 8.10 pixels mm^-1	θ_max = 25.3°, θ_min = 1.7°
ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −8→8
T_min = 0.932, T_max = 0.950	l = −36→29
20975 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0465P)² + 1.0036P] where P = (F_o² + 2F_c²)/3
5007 reflections	(Δ/σ)_max < 0.001
347 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₅H₁₄ClNO₂	V = 2770.60 (17) Å³
M_r = 275.72	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.4227 (4) Å	µ = 0.27 mm⁻¹
b = 7.3638 (2) Å	T = 296 K
c = 30.4583 (13) Å	0.35 × 0.22 × 0.20 mm
β = 96.080 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	5007 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3456 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.950	R_int = 0.026
20975 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.05	Δρ_max = 0.19 e Å⁻³
5007 reflections	Δρ_min = −0.30 e Å⁻³
347 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 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 (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	−0.47381 (6)	0.59742 (12)	0.19551 (3)	0.1029 (3)
O1	0.34541 (11)	0.7300 (2)	0.00839 (5)	0.0666 (6)
O2	0.15540 (11)	0.7756 (2)	−0.03006 (4)	0.0622 (5)
N1	−0.10335 (14)	0.6680 (2)	0.09001 (5)	0.0531 (6)
C1	−0.18906 (15)	0.6522 (3)	0.11683 (6)	0.0480 (6)
C2	−0.27949 (16)	0.5526 (3)	0.10049 (7)	0.0534 (7)
C3	−0.36655 (17)	0.5352 (3)	0.12478 (7)	0.0582 (8)
C4	−0.36430 (18)	0.6199 (3)	0.16498 (8)	0.0597 (8)
C5	−0.27691 (19)	0.7213 (3)	0.18141 (7)	0.0641 (8)
C6	−0.18948 (17)	0.7378 (3)	0.15726 (7)	0.0572 (8)
C7	−0.00599 (17)	0.6629 (3)	0.10774 (7)	0.0547 (7)
C8	0.08663 (16)	0.6815 (3)	0.08263 (7)	0.0505 (7)
C9	0.07247 (15)	0.7174 (3)	0.03730 (6)	0.0481 (7)
C10	0.15987 (16)	0.7355 (3)	0.01380 (6)	0.0477 (6)
C11	0.26563 (16)	0.7137 (3)	0.03515 (7)	0.0505 (7)
C12	0.27930 (17)	0.6779 (3)	0.07967 (7)	0.0595 (8)
C13	0.19067 (17)	0.6630 (3)	0.10334 (7)	0.0606 (8)
C14	0.45431 (17)	0.7121 (4)	0.02793 (9)	0.0797 (10)
C15	0.05181 (18)	0.8106 (4)	−0.05280 (7)	0.0704 (9)
Cl2	−0.28854 (6)	0.13333 (12)	0.26687 (2)	0.0916 (3)
O3	0.34354 (11)	0.2151 (2)	0.04035 (5)	0.0685 (6)
O4	0.53216 (11)	0.1383 (2)	0.07674 (5)	0.0614 (5)
N2	0.08863 (14)	0.1523 (2)	0.16357 (6)	0.0538 (6)
C16	0.00252 (16)	0.1438 (3)	0.19048 (6)	0.0474 (7)
C17	−0.09141 (16)	0.2363 (3)	0.17535 (7)	0.0526 (7)
C18	−0.18002 (17)	0.2347 (3)	0.19879 (7)	0.0575 (7)
C19	−0.17623 (17)	0.1391 (3)	0.23760 (7)	0.0535 (7)
C20	−0.08492 (18)	0.0463 (3)	0.25324 (7)	0.0614 (8)
C21	0.00371 (17)	0.0481 (3)	0.22977 (7)	0.0572 (7)
C22	0.18473 (17)	0.1189 (3)	0.17922 (7)	0.0597 (8)
C23	0.27594 (16)	0.1226 (3)	0.15321 (7)	0.0547 (7)
C24	0.26207 (16)	0.1687 (3)	0.10854 (7)	0.0511 (7)
C25	0.34811 (16)	0.1725 (3)	0.08394 (7)	0.0502 (7)
C26	0.45269 (15)	0.1286 (3)	0.10403 (7)	0.0515 (7)
C27	0.46640 (17)	0.0814 (3)	0.14774 (8)	0.0654 (8)
C28	0.37878 (18)	0.0795 (4)	0.17212 (8)	0.0700 (9)
C29	0.23950 (17)	0.2317 (3)	0.01634 (7)	0.0672 (8)
C30	0.63635 (16)	0.0663 (3)	0.09192 (8)	0.0675 (9)
H2	−0.28136	0.49722	0.07297	0.0640*
H3	−0.42638	0.46651	0.11397	0.0699*
H5	−0.27641	0.77864	0.20863	0.0769*
H6	−0.13016	0.80729	0.16828	0.0686*
H7	0.00653	0.64637	0.13813	0.0656*
H9	0.00291	0.72905	0.02296	0.0577*
H12	0.34870	0.66362	0.09400	0.0714*
H13	0.20112	0.64022	0.13353	0.0727*
H14A	0.46754	0.79754	0.05169	0.1193*
H14B	0.50294	0.73565	0.00611	0.1193*
H14C	0.46581	0.59102	0.03914	0.1193*
H15A	0.00931	0.70152	−0.05403	0.1056*
H15B	0.05986	0.85091	−0.08225	0.1056*
H15C	0.01616	0.90321	−0.03750	0.1056*
H17	−0.09447	0.30033	0.14893	0.0631*
H18	−0.24229	0.29817	0.18840	0.0690*
H20	−0.08271	−0.01779	0.27963	0.0737*
H21	0.06554	−0.01593	0.24041	0.0687*
H22	0.19776	0.09042	0.20906	0.0716*
H24	0.19328	0.19723	0.09526	0.0614*
H27	0.53481	0.05060	0.16104	0.0785*
H28	0.38922	0.04869	0.20187	0.0840*
H29A	0.19869	0.12289	0.01982	0.1007*
H29B	0.24729	0.24997	−0.01437	0.1007*
H29C	0.20224	0.33350	0.02736	0.1007*
H30A	0.66641	0.13300	0.11741	0.1012*
H30B	0.68330	0.07689	0.06896	0.1012*
H30C	0.62931	−0.05923	0.09960	0.1012*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0819 (5)	0.1266 (7)	0.1086 (6)	0.0040 (4)	0.0499 (4)	0.0131 (5)
O1	0.0419 (8)	0.0932 (12)	0.0652 (10)	−0.0014 (8)	0.0074 (7)	0.0011 (9)
O2	0.0502 (8)	0.0884 (11)	0.0482 (8)	0.0024 (8)	0.0058 (7)	0.0031 (8)
N1	0.0510 (10)	0.0576 (10)	0.0509 (10)	−0.0004 (8)	0.0067 (8)	0.0022 (8)
C1	0.0490 (11)	0.0469 (11)	0.0480 (11)	0.0033 (9)	0.0048 (9)	0.0062 (9)
C2	0.0576 (13)	0.0507 (12)	0.0512 (12)	0.0006 (10)	0.0028 (10)	0.0015 (10)
C3	0.0496 (12)	0.0575 (13)	0.0664 (14)	−0.0020 (10)	0.0005 (10)	0.0109 (11)
C4	0.0568 (13)	0.0607 (14)	0.0640 (14)	0.0086 (11)	0.0179 (11)	0.0117 (11)
C5	0.0749 (16)	0.0635 (14)	0.0554 (13)	0.0048 (12)	0.0139 (12)	−0.0054 (11)
C6	0.0574 (13)	0.0566 (13)	0.0572 (13)	−0.0035 (10)	0.0045 (10)	−0.0052 (10)
C7	0.0574 (13)	0.0604 (13)	0.0464 (11)	0.0015 (10)	0.0059 (10)	0.0051 (10)
C8	0.0492 (12)	0.0535 (12)	0.0487 (11)	0.0007 (9)	0.0043 (9)	0.0026 (9)
C9	0.0419 (11)	0.0496 (12)	0.0518 (12)	0.0011 (9)	0.0001 (9)	−0.0002 (9)
C10	0.0482 (11)	0.0469 (11)	0.0472 (11)	0.0005 (9)	0.0015 (9)	−0.0022 (9)
C11	0.0450 (11)	0.0514 (12)	0.0548 (12)	−0.0009 (9)	0.0043 (9)	−0.0033 (10)
C12	0.0438 (11)	0.0724 (15)	0.0601 (14)	0.0015 (10)	−0.0049 (10)	−0.0011 (11)
C13	0.0588 (13)	0.0740 (15)	0.0478 (12)	0.0017 (11)	0.0000 (10)	0.0064 (11)
C14	0.0445 (13)	0.113 (2)	0.0814 (17)	−0.0016 (13)	0.0054 (12)	−0.0137 (16)
C15	0.0656 (15)	0.0966 (18)	0.0477 (12)	0.0126 (13)	0.0000 (11)	−0.0030 (12)
Cl2	0.0734 (4)	0.1239 (6)	0.0828 (5)	0.0051 (4)	0.0329 (3)	−0.0075 (4)
O3	0.0441 (8)	0.1016 (12)	0.0596 (9)	0.0077 (8)	0.0045 (7)	0.0180 (9)
O4	0.0406 (8)	0.0748 (10)	0.0686 (10)	0.0043 (7)	0.0045 (7)	0.0094 (8)
N2	0.0529 (10)	0.0587 (11)	0.0503 (10)	0.0024 (8)	0.0072 (8)	0.0034 (8)
C16	0.0516 (12)	0.0447 (11)	0.0452 (11)	0.0001 (9)	0.0023 (9)	−0.0007 (9)
C17	0.0593 (13)	0.0538 (12)	0.0432 (11)	0.0071 (10)	−0.0019 (9)	0.0047 (9)
C18	0.0528 (12)	0.0617 (13)	0.0562 (13)	0.0120 (10)	−0.0030 (10)	−0.0051 (11)
C19	0.0538 (12)	0.0565 (12)	0.0509 (12)	0.0000 (10)	0.0094 (10)	−0.0085 (10)
C20	0.0689 (15)	0.0616 (14)	0.0543 (13)	0.0024 (11)	0.0092 (11)	0.0119 (11)
C21	0.0549 (12)	0.0573 (13)	0.0586 (13)	0.0091 (10)	0.0021 (10)	0.0126 (11)
C22	0.0588 (14)	0.0723 (15)	0.0474 (12)	0.0005 (11)	0.0035 (10)	0.0030 (11)
C23	0.0500 (12)	0.0606 (13)	0.0531 (12)	0.0010 (10)	0.0031 (10)	0.0013 (10)
C24	0.0425 (11)	0.0537 (12)	0.0564 (12)	0.0045 (9)	0.0016 (9)	0.0031 (10)
C25	0.0471 (11)	0.0496 (12)	0.0531 (12)	0.0015 (9)	0.0011 (9)	0.0050 (10)
C26	0.0423 (11)	0.0512 (12)	0.0600 (13)	0.0006 (9)	0.0005 (9)	0.0018 (10)
C27	0.0440 (12)	0.0853 (17)	0.0642 (14)	0.0044 (11)	−0.0073 (10)	0.0105 (12)
C28	0.0580 (14)	0.0963 (18)	0.0538 (13)	0.0041 (12)	−0.0028 (11)	0.0113 (13)
C29	0.0576 (13)	0.0810 (16)	0.0606 (14)	0.0047 (12)	−0.0046 (11)	0.0085 (12)
C30	0.0416 (12)	0.0733 (15)	0.0867 (17)	0.0067 (10)	0.0029 (11)	0.0070 (13)

Geometric parameters (Å, º) top

Cl1—C4	1.735 (2)	C13—H13	0.9300
Cl2—C19	1.734 (2)	C14—H14A	0.9600
O1—C11	1.354 (2)	C14—H14B	0.9600
O1—C14	1.425 (3)	C14—H14C	0.9600
O2—C15	1.419 (3)	C15—H15A	0.9600
O2—C10	1.364 (2)	C15—H15B	0.9600
O3—C25	1.360 (3)	C15—H15C	0.9600
O3—C29	1.421 (3)	C16—C17	1.387 (3)
O4—C30	1.430 (3)	C16—C21	1.388 (3)
O4—C26	1.358 (2)	C17—C18	1.374 (3)
N1—C7	1.272 (3)	C18—C19	1.372 (3)
N1—C1	1.414 (2)	C19—C20	1.366 (3)
N2—C22	1.262 (3)	C20—C21	1.375 (3)
N2—C16	1.416 (3)	C22—C23	1.450 (3)
C1—C6	1.384 (3)	C23—C24	1.395 (3)
C1—C2	1.389 (3)	C23—C28	1.382 (3)
C2—C3	1.380 (3)	C24—C25	1.369 (3)
C3—C4	1.372 (3)	C25—C26	1.414 (3)
C4—C5	1.368 (3)	C26—C27	1.369 (3)
C5—C6	1.380 (3)	C27—C28	1.381 (3)
C7—C8	1.454 (3)	C17—H17	0.9300
C8—C9	1.398 (3)	C18—H18	0.9300
C8—C13	1.384 (3)	C20—H20	0.9300
C9—C10	1.369 (3)	C21—H21	0.9300
C10—C11	1.412 (3)	C22—H22	0.9300
C11—C12	1.374 (3)	C24—H24	0.9300
C12—C13	1.383 (3)	C27—H27	0.9300
C2—H2	0.9300	C28—H28	0.9300
C3—H3	0.9300	C29—H29A	0.9600
C5—H5	0.9300	C29—H29B	0.9600
C6—H6	0.9300	C29—H29C	0.9600
C7—H7	0.9300	C30—H30A	0.9600
C9—H9	0.9300	C30—H30B	0.9600
C12—H12	0.9300	C30—H30C	0.9600

C11—O1—C14	117.62 (17)	H15A—C15—H15B	109.00
C10—O2—C15	117.28 (15)	O2—C15—H15A	109.00
C25—O3—C29	117.64 (16)	O2—C15—H15B	109.00
C26—O4—C30	118.33 (17)	N2—C16—C17	116.51 (17)
C1—N1—C7	119.52 (17)	N2—C16—C21	125.58 (19)
C16—N2—C22	121.01 (18)	C17—C16—C21	117.89 (19)
N1—C1—C6	123.42 (18)	C16—C17—C18	121.0 (2)
N1—C1—C2	117.81 (17)	C17—C18—C19	119.7 (2)
C2—C1—C6	118.70 (18)	Cl2—C19—C18	119.96 (17)
C1—C2—C3	120.48 (19)	Cl2—C19—C20	119.48 (17)
C2—C3—C4	119.6 (2)	C18—C19—C20	120.6 (2)
C3—C4—C5	121.0 (2)	C19—C20—C21	119.7 (2)
Cl1—C4—C3	119.47 (17)	C16—C21—C20	121.2 (2)
Cl1—C4—C5	119.53 (18)	N2—C22—C23	123.6 (2)
C4—C5—C6	119.5 (2)	C22—C23—C24	120.96 (18)
C1—C6—C5	120.8 (2)	C22—C23—C28	120.6 (2)
N1—C7—C8	122.94 (19)	C24—C23—C28	118.41 (19)
C7—C8—C9	120.89 (18)	C23—C24—C25	121.05 (19)
C7—C8—C13	120.26 (19)	O3—C25—C24	125.80 (19)
C9—C8—C13	118.85 (19)	O3—C25—C26	114.64 (17)
C8—C9—C10	120.72 (18)	C24—C25—C26	119.57 (19)
O2—C10—C11	114.53 (17)	O4—C26—C25	114.67 (18)
O2—C10—C9	125.53 (18)	O4—C26—C27	125.80 (18)
C9—C10—C11	119.93 (17)	C25—C26—C27	119.54 (19)
O1—C11—C10	114.68 (18)	C26—C27—C28	120.1 (2)
O1—C11—C12	126.11 (19)	C23—C28—C27	121.3 (2)
C10—C11—C12	119.21 (19)	C16—C17—H17	119.00
C11—C12—C13	120.5 (2)	C18—C17—H17	119.00
C8—C13—C12	120.8 (2)	C17—C18—H18	120.00
C1—C2—H2	120.00	C19—C18—H18	120.00
C3—C2—H2	120.00	C19—C20—H20	120.00
C2—C3—H3	120.00	C21—C20—H20	120.00
C4—C3—H3	120.00	C16—C21—H21	119.00
C4—C5—H5	120.00	C20—C21—H21	119.00
C6—C5—H5	120.00	N2—C22—H22	118.00
C1—C6—H6	120.00	C23—C22—H22	118.00
C5—C6—H6	120.00	C23—C24—H24	119.00
C8—C7—H7	119.00	C25—C24—H24	119.00
N1—C7—H7	119.00	C26—C27—H27	120.00
C8—C9—H9	120.00	C28—C27—H27	120.00
C10—C9—H9	120.00	C23—C28—H28	119.00
C11—C12—H12	120.00	C27—C28—H28	119.00
C13—C12—H12	120.00	O3—C29—H29A	109.00
C12—C13—H13	120.00	O3—C29—H29B	109.00
C8—C13—H13	120.00	O3—C29—H29C	109.00
O1—C14—H14B	109.00	H29A—C29—H29B	109.00
H14A—C14—H14C	109.00	H29A—C29—H29C	109.00
O1—C14—H14C	109.00	H29B—C29—H29C	109.00
H14A—C14—H14B	109.00	O4—C30—H30A	109.00
O1—C14—H14A	109.00	O4—C30—H30B	109.00
H14B—C14—H14C	109.00	O4—C30—H30C	109.00
O2—C15—H15C	109.00	H30A—C30—H30B	109.00
H15A—C15—H15C	109.00	H30A—C30—H30C	109.00
H15B—C15—H15C	109.00	H30B—C30—H30C	110.00

C14—O1—C11—C10	179.1 (2)	O2—C10—C11—O1	−2.1 (3)
C14—O1—C11—C12	−1.3 (3)	O2—C10—C11—C12	178.25 (19)
C15—O2—C10—C9	3.4 (3)	C9—C10—C11—O1	178.4 (2)
C15—O2—C10—C11	−176.1 (2)	C9—C10—C11—C12	−1.3 (3)
C29—O3—C25—C26	169.99 (18)	O1—C11—C12—C13	−179.5 (2)
C29—O3—C25—C24	−9.7 (3)	C10—C11—C12—C13	0.1 (3)
C30—O4—C26—C25	−169.27 (18)	C11—C12—C13—C8	0.8 (3)
C30—O4—C26—C27	10.8 (3)	N2—C16—C17—C18	179.24 (19)
C1—N1—C7—C8	−178.84 (19)	C21—C16—C17—C18	0.7 (3)
C7—N1—C1—C6	41.7 (3)	N2—C16—C21—C20	−179.1 (2)
C7—N1—C1—C2	−141.6 (2)	C17—C16—C21—C20	−0.6 (3)
C22—N2—C16—C21	−21.7 (3)	C16—C17—C18—C19	−0.5 (3)
C16—N2—C22—C23	179.0 (2)	C17—C18—C19—Cl2	−178.91 (17)
C22—N2—C16—C17	159.9 (2)	C17—C18—C19—C20	0.3 (3)
N1—C1—C6—C5	178.2 (2)	Cl2—C19—C20—C21	178.95 (17)
C6—C1—C2—C3	−1.9 (3)	C18—C19—C20—C21	−0.3 (3)
N1—C1—C2—C3	−178.78 (19)	C19—C20—C21—C16	0.5 (3)
C2—C1—C6—C5	1.5 (3)	N2—C22—C23—C24	1.6 (3)
C1—C2—C3—C4	1.2 (3)	N2—C22—C23—C28	−178.1 (2)
C2—C3—C4—Cl1	−179.88 (17)	C22—C23—C24—C25	179.9 (2)
C2—C3—C4—C5	−0.1 (3)	C28—C23—C24—C25	−0.4 (3)
Cl1—C4—C5—C6	179.46 (17)	C22—C23—C28—C27	179.6 (2)
C3—C4—C5—C6	−0.3 (3)	C24—C23—C28—C27	0.0 (4)
C4—C5—C6—C1	−0.4 (3)	C23—C24—C25—O3	179.9 (2)
N1—C7—C8—C9	3.9 (3)	C23—C24—C25—C26	0.2 (3)
N1—C7—C8—C13	−175.8 (2)	O3—C25—C26—O4	0.8 (3)
C7—C8—C9—C10	179.8 (2)	O3—C25—C26—C27	−179.21 (19)
C9—C8—C13—C12	−0.6 (3)	C24—C25—C26—O4	−179.42 (19)
C13—C8—C9—C10	−0.5 (3)	C24—C25—C26—C27	0.5 (3)
C7—C8—C13—C12	179.1 (2)	O4—C26—C27—C28	179.0 (2)
C8—C9—C10—C11	1.5 (3)	C25—C26—C27—C28	−1.0 (3)
C8—C9—C10—O2	−178.0 (2)	C26—C27—C28—C23	0.7 (4)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C8–C13 and C16–C21 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O3ⁱ	0.96	2.52	3.468 (3)	170
C6—H6···Cg3ⁱⁱ	0.93	2.85	3.602 (2)	139
C18—H18···Cg1	0.93	2.89	3.588 (2)	133
C21—H21···Cg3ⁱⁱⁱ	0.93	2.88	3.549 (2)	130
C29—H29C···Cg2	0.96	2.88	3.782 (2)	157
C30—H30C···Cg1^iv	0.96	2.76	3.613 (2)	148

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄ClNO₂
M_r	275.72
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.4227 (4), 7.3638 (2), 30.4583 (13)
β (°)	96.080 (2)
V (Å³)	2770.60 (17)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.35 × 0.22 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.932, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	20975, 5007, 3456
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.120, 1.05
No. of reflections	5007
No. of parameters	347
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.30

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C8–C13 and C16–C21 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O3ⁱ	0.96	2.52	3.468 (3)	170
C6—H6···Cg3ⁱⁱ	0.93	2.85	3.602 (2)	139
C18—H18···Cg1	0.93	2.89	3.588 (2)	133
C21—H21···Cg3ⁱⁱⁱ	0.93	2.88	3.549 (2)	130
C29—H29C···Cg2	0.96	2.88	3.782 (2)	157
C30—H30C···Cg1^iv	0.96	2.76	3.613 (2)	148

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

Acknowledgements

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

References

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dehno Khalaji, A., Asghari, J., Fejfarová, K. & Dušek, M. (2009). Acta Cryst. E65, o253. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Shang, Z.-H. & Tan, S. (2007). Acta Cryst. E63, o2960–o2961. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals 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 66| Part 9| September 2010| Page o2355

https://doi.org/10.1107/S1600536810032782

Open

access