4-[(9-Ethyl-9H-carbazol-3-yl)methyl­idene­amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Asiri, A.M.; Khan, S.A.; Tan, K.W.; Ng, S.W.

doi:10.1107/S1600536810023779

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1782

doi:10.1107/S1600536810023779

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4-[(9-Ethyl-9H-carbazol-3-yl)methylideneamino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Abdullah M. Asiri,^a Salman A. Khan,^a Kong Wai Tan ^b and Seik Weng Ng ^b ^*

^aChemistry Department, Faculty of Science, King Abdul Aziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 15 June 2010; accepted 19 June 2010; online 26 June 2010)

The imino–carbon double bond in the title Schiff base, C₂₆H₂₄N₄O, has an E configuration. The 13-membered carbazolyl fused-ring (r.m.s. deviation = 0.056 Å) is nearly coplanar with five-membered pyrazole ring (r.m.s. deviation = 0.036 Å) [dihedral angle between the two systems = 10.4 (1)°]; the phenyl substituent is twisted by 51.1 (1)° with respect to the five-membered ring.

Related literature

For background to this class of Schiff bases, see: Montalvo-González & Ariza-Castolo (2003 ).

Experimental

Crystal data

C₂₆H₂₄N₄O
M_r = 408.49
Monoclinic, P 2₁ /n
a = 10.4458 (6) Å
b = 18.2674 (11) Å
c = 10.8989 (6) Å
β = 96.127 (1)°
V = 2067.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.25 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
19772 measured reflections
4756 independent reflections
4000 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.104
S = 1.02
4756 reflections
283 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023779/jh2169sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810023779/jh2169Isup2.hkl

checkCIF report

Comment top

4-Aminoantipyrine (4-amino-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one) possesses a pyrazolone unit, a feature that is important to the design of non-steroidal anti-inflammatory chemicals. Its amino group group allows the chemical to condense with aromatic aldehydes to yield Schiff bases. The crystal structures of a large number of such Schiff bases have been reported. For the Schiff base derived from the benzaldehyde homolog, the phenyl and pyrazoly rings are nearly coplanar (Montalvo-González & Ariza-Castolo, 2003). In the title carbazole-aldehyde analog (Scheme I, Fig. 1), the 13-membered carbazolyl fused-ring is nearly coplanar with 5-membered pyrazolyl ring [dihedral angle between the two systems 10.4 (1) °]. The phenyl substituent is twisted by 51.1 (1) ° with respect to the 5-membered ring.

Related literature top

For background to this class of Schiff bases, see: Montalvo-González & Ariza-Castolo (2003).

Experimental top

9-Ethylcarbazole-3-carboxaldehyde (0.50 g, 2.2 mmol) and 4-aminoantipyrine (0.45 g, 2.2 mmol) here heated in methanol (15 ml) for 5 h to afford a light yellow precipitate. The solid material was collected and recrystallized from methanol.

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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₆H₂₄N₄O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

4-[(9-Ethyl-9H-carbazol-3-yl)methylideneamino]-1,5-dimethyl- 2-phenyl-1H-pyrazol-3(2H)-one top

Crystal data top

C₂₆H₂₄N₄O	F(000) = 864
M_r = 408.49	D_x = 1.312 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7258 reflections
a = 10.4458 (6) Å	θ = 2.2–28.3°
b = 18.2674 (11) Å	µ = 0.08 mm⁻¹
c = 10.8989 (6) Å	T = 100 K
β = 96.127 (1)°	Prism, yellow
V = 2067.8 (2) Å³	0.25 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	4000 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.031
Graphite monochromator	θ_max = 27.5°, θ_min = 2.2°
ω scans	h = −13→13
19772 measured reflections	k = −23→23
4756 independent reflections	l = −14→14

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0525P)² + 0.720P] where P = (F_o² + 2F_c²)/3
4756 reflections	(Δ/σ)_max < 0.001
283 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₆H₂₄N₄O	V = 2067.8 (2) Å³
M_r = 408.49	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.4458 (6) Å	µ = 0.08 mm⁻¹
b = 18.2674 (11) Å	T = 100 K
c = 10.8989 (6) Å	0.25 × 0.20 × 0.20 mm
β = 96.127 (1)°

Data collection top

Bruker SMART APEX diffractometer	4000 reflections with I > 2σ(I)
19772 measured reflections	R_int = 0.031
4756 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.02	Δρ_max = 0.24 e Å⁻³
4756 reflections	Δρ_min = −0.25 e Å⁻³
283 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.60645 (8)	0.54578 (4)	0.40022 (8)	0.02038 (19)
N1	1.35714 (9)	0.68186 (6)	0.65745 (9)	0.0206 (2)
N2	0.75630 (9)	0.69353 (6)	0.47222 (9)	0.0175 (2)
N3	0.43648 (9)	0.70479 (5)	0.32066 (9)	0.0178 (2)
N4	0.44409 (9)	0.62867 (5)	0.33728 (9)	0.0179 (2)
C1	1.36337 (11)	0.75748 (7)	0.66819 (11)	0.0196 (2)
C2	1.46850 (12)	0.80129 (8)	0.70917 (12)	0.0250 (3)
H2	1.5508	0.7805	0.7330	0.030*
C3	1.44906 (13)	0.87620 (8)	0.71402 (12)	0.0269 (3)
H3	1.5192	0.9072	0.7419	0.032*
C4	1.32833 (13)	0.90704 (7)	0.67875 (11)	0.0255 (3)
H4	1.3177	0.9586	0.6833	0.031*
C5	1.22368 (12)	0.86349 (7)	0.63713 (11)	0.0213 (3)
H5	1.1420	0.8848	0.6126	0.026*
C6	1.24060 (11)	0.78774 (7)	0.63197 (10)	0.0178 (2)
C7	1.15504 (11)	0.72649 (6)	0.60145 (10)	0.0165 (2)
C8	1.02461 (11)	0.72027 (6)	0.56055 (10)	0.0167 (2)
H8	0.9737	0.7629	0.5434	0.020*
C9	0.96945 (11)	0.65098 (6)	0.54505 (10)	0.0172 (2)
C10	1.04661 (12)	0.58849 (6)	0.57261 (11)	0.0193 (2)
H10	1.0070	0.5416	0.5660	0.023*
C11	1.17744 (11)	0.59244 (6)	0.60877 (11)	0.0196 (2)
H11	1.2283	0.5496	0.6241	0.023*
C12	1.23104 (11)	0.66235 (7)	0.62169 (10)	0.0179 (2)
C13	1.46091 (11)	0.63045 (7)	0.69520 (11)	0.0223 (3)
H13A	1.5445	0.6535	0.6832	0.027*
H13B	1.4509	0.5864	0.6420	0.027*
C14	1.46196 (15)	0.60749 (9)	0.82923 (13)	0.0357 (3)
H14A	1.5318	0.5723	0.8501	0.054*
H14B	1.3794	0.5847	0.8416	0.054*
H14C	1.4754	0.6506	0.8825	0.054*
C15	0.83444 (11)	0.63985 (6)	0.49658 (10)	0.0175 (2)
H15	0.8037	0.5913	0.4827	0.021*
C16	0.56810 (11)	0.60962 (6)	0.38971 (10)	0.0165 (2)
C17	0.63052 (11)	0.67924 (6)	0.42004 (10)	0.0163 (2)
C18	0.54672 (11)	0.73382 (6)	0.37959 (10)	0.0169 (2)
C19	0.56536 (12)	0.81422 (6)	0.39240 (11)	0.0208 (3)
H19A	0.5360	0.8382	0.3139	0.031*
H19B	0.6569	0.8248	0.4147	0.031*
H19C	0.5155	0.8327	0.4571	0.031*
C20	0.31008 (11)	0.73921 (7)	0.31473 (12)	0.0221 (3)
H20A	0.3203	0.7914	0.3339	0.033*
H20B	0.2596	0.7160	0.3748	0.033*
H20C	0.2654	0.7334	0.2316	0.033*
C21	0.35842 (11)	0.58088 (6)	0.26541 (10)	0.0170 (2)
C22	0.31925 (12)	0.59525 (7)	0.14157 (11)	0.0207 (3)
H22	0.3482	0.6380	0.1034	0.025*
C23	0.23735 (12)	0.54634 (7)	0.07451 (11)	0.0217 (3)
H23	0.2100	0.5560	−0.0099	0.026*
C24	0.19515 (11)	0.48364 (7)	0.12940 (11)	0.0209 (3)
H24	0.1394	0.4503	0.0830	0.025*
C25	0.23514 (12)	0.47000 (7)	0.25284 (11)	0.0208 (2)
H25	0.2067	0.4269	0.2906	0.025*
C26	0.31609 (11)	0.51841 (6)	0.32186 (11)	0.0186 (2)
H26	0.3422	0.5090	0.4066	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0190 (4)	0.0166 (4)	0.0248 (4)	0.0015 (3)	−0.0012 (3)	0.0022 (3)
N1	0.0129 (5)	0.0230 (5)	0.0254 (5)	0.0016 (4)	−0.0005 (4)	−0.0015 (4)
N2	0.0141 (5)	0.0215 (5)	0.0164 (4)	−0.0007 (4)	−0.0006 (4)	−0.0016 (4)
N3	0.0157 (5)	0.0142 (5)	0.0227 (5)	0.0007 (4)	−0.0022 (4)	0.0005 (4)
N4	0.0160 (5)	0.0145 (5)	0.0222 (5)	−0.0003 (4)	−0.0030 (4)	0.0019 (4)
C1	0.0169 (6)	0.0236 (6)	0.0187 (5)	−0.0015 (5)	0.0040 (4)	−0.0004 (4)
C2	0.0173 (6)	0.0327 (7)	0.0250 (6)	−0.0050 (5)	0.0031 (5)	−0.0012 (5)
C3	0.0263 (6)	0.0318 (7)	0.0229 (6)	−0.0139 (5)	0.0040 (5)	−0.0009 (5)
C4	0.0346 (7)	0.0208 (6)	0.0214 (6)	−0.0079 (5)	0.0043 (5)	0.0010 (5)
C5	0.0249 (6)	0.0203 (6)	0.0186 (5)	−0.0017 (5)	0.0024 (5)	0.0018 (4)
C6	0.0166 (5)	0.0219 (6)	0.0153 (5)	−0.0020 (4)	0.0029 (4)	0.0001 (4)
C7	0.0174 (6)	0.0171 (5)	0.0153 (5)	0.0005 (4)	0.0027 (4)	0.0000 (4)
C8	0.0162 (5)	0.0178 (5)	0.0159 (5)	0.0017 (4)	0.0009 (4)	0.0002 (4)
C9	0.0155 (5)	0.0204 (6)	0.0154 (5)	0.0008 (4)	0.0009 (4)	−0.0015 (4)
C10	0.0207 (6)	0.0167 (6)	0.0201 (5)	−0.0003 (4)	0.0006 (4)	−0.0033 (4)
C11	0.0190 (6)	0.0175 (6)	0.0218 (6)	0.0042 (4)	0.0002 (4)	−0.0023 (4)
C12	0.0142 (5)	0.0222 (6)	0.0173 (5)	0.0018 (4)	0.0009 (4)	−0.0012 (4)
C13	0.0141 (5)	0.0283 (6)	0.0243 (6)	0.0055 (5)	0.0010 (4)	−0.0021 (5)
C14	0.0337 (8)	0.0478 (9)	0.0254 (7)	0.0170 (7)	0.0021 (6)	0.0019 (6)
C15	0.0174 (5)	0.0190 (6)	0.0159 (5)	−0.0016 (4)	0.0004 (4)	−0.0016 (4)
C16	0.0142 (5)	0.0212 (6)	0.0138 (5)	−0.0005 (4)	0.0002 (4)	0.0017 (4)
C17	0.0157 (5)	0.0185 (6)	0.0147 (5)	−0.0008 (4)	0.0011 (4)	−0.0008 (4)
C18	0.0157 (5)	0.0198 (6)	0.0149 (5)	−0.0013 (4)	0.0009 (4)	−0.0016 (4)
C19	0.0218 (6)	0.0172 (6)	0.0226 (6)	0.0001 (5)	−0.0017 (5)	−0.0023 (4)
C20	0.0167 (6)	0.0225 (6)	0.0265 (6)	0.0028 (5)	−0.0001 (5)	0.0001 (5)
C21	0.0128 (5)	0.0174 (5)	0.0202 (5)	−0.0003 (4)	0.0000 (4)	−0.0006 (4)
C22	0.0215 (6)	0.0188 (6)	0.0215 (6)	−0.0037 (5)	0.0003 (5)	0.0039 (4)
C23	0.0238 (6)	0.0216 (6)	0.0188 (6)	−0.0006 (5)	−0.0024 (5)	0.0012 (5)
C24	0.0182 (6)	0.0187 (6)	0.0251 (6)	−0.0020 (5)	−0.0001 (5)	−0.0036 (5)
C25	0.0203 (6)	0.0168 (6)	0.0256 (6)	−0.0017 (5)	0.0043 (5)	0.0025 (5)
C26	0.0172 (5)	0.0199 (6)	0.0185 (5)	0.0017 (4)	0.0020 (4)	0.0021 (4)

Geometric parameters (Å, º) top

O1—C16	1.2344 (14)	C11—C12	1.3956 (17)
N1—C12	1.3799 (15)	C11—H11	0.9500
N1—C1	1.3873 (16)	C13—C14	1.5187 (18)
N1—C13	1.4598 (15)	C13—H13A	0.9900
N2—C15	1.2853 (15)	C13—H13B	0.9900
N2—C17	1.3994 (14)	C14—H14A	0.9800
N3—C18	1.3646 (14)	C14—H14B	0.9800
N3—N4	1.4034 (13)	C14—H14C	0.9800
N3—C20	1.4577 (15)	C15—H15	0.9500
N4—C16	1.4028 (14)	C16—C17	1.4511 (16)
N4—C21	1.4237 (14)	C17—C18	1.3682 (16)
C1—C2	1.3933 (17)	C18—C19	1.4861 (16)
C1—C6	1.4134 (16)	C19—H19A	0.9800
C2—C3	1.385 (2)	C19—H19B	0.9800
C2—H2	0.9500	C19—H19C	0.9800
C3—C4	1.397 (2)	C20—H20A	0.9800
C3—H3	0.9500	C20—H20B	0.9800
C4—C5	1.3884 (17)	C20—H20C	0.9800
C4—H4	0.9500	C21—C26	1.3907 (16)
C5—C6	1.3969 (17)	C21—C22	1.3929 (16)
C5—H5	0.9500	C22—C23	1.3895 (16)
C6—C7	1.4484 (16)	C22—H22	0.9500
C7—C8	1.3922 (16)	C23—C24	1.3857 (17)
C7—C12	1.4192 (16)	C23—H23	0.9500
C8—C9	1.3935 (16)	C24—C25	1.3880 (17)
C8—H8	0.9500	C24—H24	0.9500
C9—C10	1.4112 (16)	C25—C26	1.3881 (16)
C9—C15	1.4664 (15)	C25—H25	0.9500
C10—C11	1.3832 (16)	C26—H26	0.9500
C10—H10	0.9500

C12—N1—C1	108.40 (10)	C14—C13—H13B	109.2
C12—N1—C13	124.84 (10)	H13A—C13—H13B	107.9
C1—N1—C13	126.16 (10)	C13—C14—H14A	109.5
C15—N2—C17	119.32 (10)	C13—C14—H14B	109.5
C18—N3—N4	106.92 (9)	H14A—C14—H14B	109.5
C18—N3—C20	124.62 (10)	C13—C14—H14C	109.5
N4—N3—C20	118.15 (9)	H14A—C14—H14C	109.5
C16—N4—N3	109.60 (9)	H14B—C14—H14C	109.5
C16—N4—C21	124.82 (10)	N2—C15—C9	122.27 (11)
N3—N4—C21	120.86 (9)	N2—C15—H15	118.9
N1—C1—C2	128.85 (11)	C9—C15—H15	118.9
N1—C1—C6	109.44 (10)	O1—C16—N4	123.27 (10)
C2—C1—C6	121.70 (12)	O1—C16—C17	132.33 (11)
C3—C2—C1	117.77 (12)	N4—C16—C17	104.38 (9)
C3—C2—H2	121.1	C18—C17—N2	122.39 (10)
C1—C2—H2	121.1	C18—C17—C16	107.99 (10)
C2—C3—C4	121.29 (12)	N2—C17—C16	129.46 (10)
C2—C3—H3	119.4	N3—C18—C17	110.31 (10)
C4—C3—H3	119.4	N3—C18—C19	121.59 (10)
C5—C4—C3	121.00 (12)	C17—C18—C19	128.09 (10)
C5—C4—H4	119.5	C18—C19—H19A	109.5
C3—C4—H4	119.5	C18—C19—H19B	109.5
C4—C5—C6	118.82 (12)	H19A—C19—H19B	109.5
C4—C5—H5	120.6	C18—C19—H19C	109.5
C6—C5—H5	120.6	H19A—C19—H19C	109.5
C5—C6—C1	119.41 (11)	H19B—C19—H19C	109.5
C5—C6—C7	134.17 (11)	N3—C20—H20A	109.5
C1—C6—C7	106.34 (10)	N3—C20—H20B	109.5
C8—C7—C12	119.64 (10)	H20A—C20—H20B	109.5
C8—C7—C6	134.06 (11)	N3—C20—H20C	109.5
C12—C7—C6	106.30 (10)	H20A—C20—H20C	109.5
C7—C8—C9	119.39 (11)	H20B—C20—H20C	109.5
C7—C8—H8	120.3	C26—C21—C22	120.59 (11)
C9—C8—H8	120.3	C26—C21—N4	118.08 (10)
C8—C9—C10	119.31 (10)	C22—C21—N4	121.33 (10)
C8—C9—C15	122.61 (10)	C23—C22—C21	119.29 (11)
C10—C9—C15	118.04 (10)	C23—C22—H22	120.4
C11—C10—C9	122.89 (11)	C21—C22—H22	120.4
C11—C10—H10	118.6	C24—C23—C22	120.71 (11)
C9—C10—H10	118.6	C24—C23—H23	119.6
C10—C11—C12	116.75 (11)	C22—C23—H23	119.6
C10—C11—H11	121.6	C23—C24—C25	119.35 (11)
C12—C11—H11	121.6	C23—C24—H24	120.3
N1—C12—C11	128.71 (11)	C25—C24—H24	120.3
N1—C12—C7	109.39 (10)	C26—C25—C24	120.92 (11)
C11—C12—C7	121.87 (10)	C26—C25—H25	119.5
N1—C13—C14	112.18 (10)	C24—C25—H25	119.5
N1—C13—H13A	109.2	C25—C26—C21	119.14 (11)
C14—C13—H13A	109.2	C25—C26—H26	120.4
N1—C13—H13B	109.2	C21—C26—H26	120.4

C18—N3—N4—C16	−9.38 (12)	C8—C7—C12—C11	−3.85 (17)
C20—N3—N4—C16	−156.12 (10)	C6—C7—C12—C11	175.87 (11)
C18—N3—N4—C21	−166.14 (10)	C12—N1—C13—C14	−81.94 (15)
C20—N3—N4—C21	47.12 (15)	C1—N1—C13—C14	88.12 (15)
C12—N1—C1—C2	175.55 (12)	C17—N2—C15—C9	176.64 (10)
C13—N1—C1—C2	4.1 (2)	C8—C9—C15—N2	−4.26 (18)
C12—N1—C1—C6	−3.37 (13)	C10—C9—C15—N2	178.02 (11)
C13—N1—C1—C6	−174.79 (11)	N3—N4—C16—O1	−170.71 (10)
N1—C1—C2—C3	−178.53 (12)	C21—N4—C16—O1	−15.08 (18)
C6—C1—C2—C3	0.28 (18)	N3—N4—C16—C17	7.67 (12)
C1—C2—C3—C4	−0.18 (19)	C21—N4—C16—C17	163.30 (10)
C2—C3—C4—C5	−0.24 (19)	C15—N2—C17—C18	−172.81 (11)
C3—C4—C5—C6	0.56 (18)	C15—N2—C17—C16	1.92 (18)
C4—C5—C6—C1	−0.46 (17)	O1—C16—C17—C18	174.95 (12)
C4—C5—C6—C7	175.81 (12)	N4—C16—C17—C18	−3.22 (12)
N1—C1—C6—C5	179.06 (10)	O1—C16—C17—N2	−0.4 (2)
C2—C1—C6—C5	0.04 (17)	N4—C16—C17—N2	−178.54 (11)
N1—C1—C6—C7	1.84 (13)	N4—N3—C18—C17	7.25 (13)
C2—C1—C6—C7	−177.17 (11)	C20—N3—C18—C17	151.26 (11)
C5—C6—C7—C8	3.4 (2)	N4—N3—C18—C19	−173.40 (10)
C1—C6—C7—C8	179.98 (12)	C20—N3—C18—C19	−29.39 (17)
C5—C6—C7—C12	−176.29 (13)	N2—C17—C18—N3	173.21 (10)
C1—C6—C7—C12	0.32 (12)	C16—C17—C18—N3	−2.51 (13)
C12—C7—C8—C9	2.68 (17)	N2—C17—C18—C19	−6.09 (19)
C6—C7—C8—C9	−176.94 (12)	C16—C17—C18—C19	178.19 (11)
C7—C8—C9—C10	0.78 (16)	C16—N4—C21—C26	62.98 (15)
C7—C8—C9—C15	−176.91 (10)	N3—N4—C21—C26	−143.95 (11)
C8—C9—C10—C11	−3.41 (17)	C16—N4—C21—C22	−116.02 (13)
C15—C9—C10—C11	174.39 (11)	N3—N4—C21—C22	37.05 (16)
C9—C10—C11—C12	2.29 (18)	C26—C21—C22—C23	−0.13 (18)
C1—N1—C12—C11	−174.53 (12)	N4—C21—C22—C23	178.84 (11)
C13—N1—C12—C11	−2.97 (19)	C21—C22—C23—C24	−0.31 (19)
C1—N1—C12—C7	3.58 (13)	C22—C23—C24—C25	0.22 (19)
C13—N1—C12—C7	175.14 (10)	C23—C24—C25—C26	0.31 (18)
C10—C11—C12—N1	179.23 (11)	C24—C25—C26—C21	−0.74 (18)
C10—C11—C12—C7	1.34 (17)	C22—C21—C26—C25	0.65 (18)
C8—C7—C12—N1	177.90 (10)	N4—C21—C26—C25	−178.36 (10)
C6—C7—C12—N1	−2.39 (13)

Experimental details

Crystal data
Chemical formula	C₂₆H₂₄N₄O
M_r	408.49
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	10.4458 (6), 18.2674 (11), 10.8989 (6)
β (°)	96.127 (1)
V (Å³)	2067.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	19772, 4756, 4000
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.104, 1.02
No. of reflections	4756
No. of parameters	283
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.25

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

We thank King Abdul Aziz University and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Montalvo-González, R. & Ariza-Castolo, A. (2003). J. Mol. Struct. 655, 375–389. Web of Science CSD 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. (2010). J. Appl. Cryst. 43. Submitted. Google Scholar

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