5-(4-Methoxy­phen­yl)-1-(4-methyl­phen­yl)-1H-pyrazol-3-ol

Sun, Y.-F.; Jia, H.-S.; Liu, S.; Zhu, H.-J.

doi:10.1107/S1600536807031686

Buy article online - an online subscription or single-article purchase is required to access this article.

5-(4-Methoxyphenyl)-1-(4-methylphenyl)-1H-pyrazol-3-ol

Y.-F. Sun, H.-S. Jia, S. Liu and H.-J. Zhu

The asymmetric unit of the title compound, C₁₇H₁₆N₂O₂, contains two crystallographically independent molecules, with methylphenyl and methoxyphenyl substituents in different orientations with respect to the pyrazole ring. In the crystal structure, intermolecular O—H

N and C—H

O hydrogen bonds link the molecules; the O—H

N bonds generate centrosymmetric dimers, and these are connected by C—H

O bonds to generate one-dimensional double-stranded chains.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031686/hk2281sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031686/hk2281Isup2.hkl Contains datablock I

CCDC reference: 657681

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.007 Å
R factor = 0.077
wR factor = 0.225
Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)       3000 Deg.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

In the process of synthesis, we obtained the title compound, (I), and we herein report its crystal structure.

The asymmetric unit of the title compound, (I), contains two crystallographically independent molecules, with methylphenyl and methoxyphenyl substituents in different orientations with respect to the pyrazole ring (Fig. 1). The bond lengths and angles are generally within normal ranges (Allen et al., 1987).

The rings A (N1/N2/C8—C10), B (C2—C7), C (C11—C16) and A' (N3/N4/C25—C27), B' (C19—C24), C' (C28—C33) are, of course, planar and they are oriented at diheral angles of A/B = 53.93 (2)°, A/C = 39.63 (3)°, B/C = 64.37 (2)° and A'/B' = 45.45 (2)°, A'/C' = 48.66 (3)°, B'/C' = 51.98 (3)°.

In the crystal structure, intermolecular O—H···N and C—H···O hydrogen bonds (Table 1) link the molecules, in which O—H···N bonds generate the centrosymmetric dimers, and they are connected by C—H···O bonds to generate one-dimensional double-stranded chains (Fig. 2).

Related literature top

For bond-length data, see: Allen et al. (1987). For related literature, see: Masahiko & Kazuyoshi (1999); Zhu et al. (2004).

Experimental top

For the preparation of the title compound, (I), 5-(4-Methoxyphenyl)-1-p -tolylpyrazolidin-3-one, (II), was firstly prepared and recrystallized from ethanol, according to the literature method (Masahiko & Kazuyoshi, 1999). Then, compound (II) (4.2 g, 15 mmol) was dissolved in dimethyl- formamide (100 ml) and mixed with FeCl₃ (0.3 g, 1.5 mmol) (Zhu et al., 2004). The mixture was heated to 353 K and maintained at that temperature for 1 h, and then stirred for 12 h without heating. The reaction mixture was then poured into water (500 ml). The precipitate which formed was filtered off, washed with water and dried under reduced pressure. The crude product was then crystallized from ethanol to give (I) (yield; 2.8 g, 10 mmol). Crystals of (I) suitable for X-ray analysis were grown by slow evaporation of a solution in acetic ether at room temperature about 7 d.

Structure description top

In the process of synthesis, we obtained the title compound, (I), and we herein report its crystal structure.

For bond-length data, see: Allen et al. (1987). For related literature, see: Masahiko & Kazuyoshi (1999); Zhu et al. (2004).

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1985); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level.
	Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.

5-(4-Methoxyphenyl)-1-(4-methylphenyl)-1H-pyrazol-3-ol top

Crystal data top

C₁₇H₁₆N₂O₂	Z = 4
M_r = 280.32	F(000) = 592
Triclinic, P1	D_x = 1.271 Mg m⁻³
Hall symbol: -P 1	Melting point: 515 K
a = 9.2520 (19) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.160 (2) Å	Cell parameters from 25 reflections
c = 16.338 (3) Å	θ = 9–12°
α = 90.72 (3)°	µ = 0.09 mm⁻¹
β = 91.97 (3)°	T = 298 K
γ = 107.34 (3)°	Needle, colorless
V = 1464.7 (6) Å³	0.40 × 0.10 × 0.10 mm

Data collection top

Enraf-Nonius CAD-4 diffractometer	2899 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.056
Graphite monochromator	θ_max = 26.0°, θ_min = 1.3°
ω/2θ scans	h = −11→11
Absorption correction: ψ scan (North et al., 1968)	k = −12→12
T_min = 0.975, T_max = 0.990	l = 0→20
6130 measured reflections	3 standard reflections every 120 min
5754 independent reflections	intensity decay: none

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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.225	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.05P)² + 2.P] where P = (F_o² + 2F_c²)/3
5754 reflections	(Δ/σ)_max = 0.002
379 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₇H₁₆N₂O₂	γ = 107.34 (3)°
M_r = 280.32	V = 1464.7 (6) Å³
Triclinic, P1	Z = 4
a = 9.2520 (19) Å	Mo Kα radiation
b = 10.160 (2) Å	µ = 0.09 mm⁻¹
c = 16.338 (3) Å	T = 298 K
α = 90.72 (3)°	0.40 × 0.10 × 0.10 mm
β = 91.97 (3)°

Data collection top

Enraf-Nonius CAD-4 diffractometer	2899 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.056
T_min = 0.975, T_max = 0.990	3 standard reflections every 120 min
6130 measured reflections	intensity decay: none
5754 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.077	0 restraints
wR(F²) = 0.225	H-atom parameters constrained
S = 1.09	Δρ_max = 0.32 e Å⁻³
5754 reflections	Δρ_min = −0.28 e Å⁻³
379 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.

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
O1	0.3812 (4)	0.3092 (3)	0.4980 (3)	0.0922 (13)
H1E	0.4660	0.3544	0.5206	0.111*
O2	−0.4318 (4)	0.4092 (4)	0.2242 (2)	0.0857 (11)
N1	0.3451 (4)	0.5152 (4)	0.4561 (3)	0.0688 (11)
N2	0.2291 (4)	0.5472 (4)	0.4138 (2)	0.0651 (11)
C1	0.3833 (6)	1.1069 (5)	0.3103 (4)	0.0936 (18)
H1B	0.4116	1.1693	0.3568	0.140*
H1C	0.3011	1.1249	0.2797	0.140*
H1D	0.4684	1.1197	0.2760	0.140*
C2	0.3336 (5)	0.9587 (5)	0.3397 (3)	0.0626 (12)
C3	0.2867 (5)	0.8513 (5)	0.2808 (3)	0.0646 (13)
H3A	0.2808	0.8708	0.2255	0.078*
C4	0.2493 (5)	0.7155 (5)	0.3057 (3)	0.0639 (13)
H4A	0.2175	0.6435	0.2673	0.077*
C5	0.2593 (5)	0.6883 (5)	0.3867 (3)	0.0611 (12)
C6	0.3034 (5)	0.7945 (5)	0.4455 (3)	0.0662 (13)
H6A	0.3060	0.7753	0.5010	0.079*
C7	0.3429 (5)	0.9281 (5)	0.4198 (4)	0.0709 (14)
H7A	0.3770	0.9997	0.4585	0.085*
C8	0.2978 (6)	0.3788 (5)	0.4612 (3)	0.0725 (14)
C9	0.1579 (5)	0.3230 (5)	0.4217 (3)	0.0740 (14)
H9A	0.1031	0.2301	0.4164	0.089*
C10	0.1164 (5)	0.4329 (5)	0.3919 (3)	0.0663 (13)
C11	−0.0252 (5)	0.4331 (5)	0.3476 (3)	0.0617 (12)
C12	−0.0911 (5)	0.3309 (5)	0.2886 (3)	0.0726 (14)
H12A	−0.0419	0.2663	0.2754	0.087*
C13	−0.2264 (5)	0.3234 (5)	0.2498 (3)	0.0763 (15)
H13A	−0.2710	0.2515	0.2126	0.092*
C14	−0.2975 (5)	0.4228 (5)	0.2658 (3)	0.0670 (13)
C15	−0.2348 (6)	0.5255 (6)	0.3244 (4)	0.0844 (17)
H15A	−0.2834	0.5907	0.3373	0.101*
C16	−0.0983 (5)	0.5290 (5)	0.3634 (3)	0.0760 (15)
H16A	−0.0547	0.5993	0.4017	0.091*
C17	−0.5285 (6)	0.4835 (7)	0.2533 (4)	0.101 (2)
H17A	−0.6190	0.4625	0.2188	0.151*
H17B	−0.4771	0.5806	0.2523	0.151*
H17C	−0.5547	0.4576	0.3084	0.151*
O3	0.5366 (4)	0.9271 (4)	−0.1042 (2)	0.0901 (12)
H3C	0.4917	0.9760	−0.0826	0.135*
O4	1.2470 (4)	0.5589 (4)	0.0961 (2)	0.0795 (10)
N3	0.6276 (4)	0.9259 (4)	0.0300 (2)	0.0618 (10)
N4	0.7377 (4)	0.8768 (4)	0.0654 (2)	0.0609 (10)
C18	0.8710 (7)	0.9521 (6)	0.4095 (3)	0.0938 (18)
H18A	0.9787	0.9828	0.4203	0.141*
H18B	0.8286	0.8649	0.4348	0.141*
H18C	0.8269	1.0186	0.4315	0.141*
C19	0.8381 (5)	0.9361 (5)	0.3186 (3)	0.0607 (12)
C20	0.9493 (5)	0.9620 (5)	0.2624 (3)	0.0629 (12)
H20A	1.0497	0.9923	0.2817	0.076*
C21	0.9209 (5)	0.9459 (5)	0.1793 (3)	0.0586 (12)
H21A	1.0001	0.9647	0.1435	0.070*
C22	0.7713 (5)	0.9008 (4)	0.1499 (3)	0.0532 (11)
C23	0.6570 (5)	0.8759 (5)	0.2060 (3)	0.0597 (12)
H23A	0.5563	0.8462	0.1870	0.072*
C24	0.6890 (5)	0.8938 (5)	0.2871 (3)	0.0687 (13)
H24A	0.6099	0.8775	0.3229	0.082*
C25	0.6305 (6)	0.8974 (5)	−0.0495 (3)	0.0649 (13)
C26	0.7356 (6)	0.8242 (5)	−0.0640 (3)	0.0691 (13)
H26A	0.7548	0.7895	−0.1141	0.083*
C27	0.8022 (5)	0.8151 (5)	0.0092 (3)	0.0593 (12)
C28	0.9197 (5)	0.7482 (5)	0.0309 (3)	0.0578 (11)
C29	1.0511 (5)	0.7743 (5)	−0.0123 (3)	0.0696 (13)
H29A	1.0642	0.8343	−0.0559	0.083*
C30	1.1634 (5)	0.7144 (5)	0.0070 (3)	0.0706 (14)
H30A	1.2509	0.7346	−0.0227	0.085*
C31	1.1442 (5)	0.6256 (5)	0.0699 (3)	0.0602 (12)
C32	1.0140 (5)	0.5950 (5)	0.1143 (3)	0.0623 (12)
H32A	1.0013	0.5335	0.1570	0.075*
C33	0.9034 (5)	0.6563 (5)	0.0946 (3)	0.0574 (11)
H33A	0.8161	0.6357	0.1246	0.069*
C34	1.3763 (5)	0.5759 (6)	0.0480 (4)	0.0854 (17)
H34A	1.4398	0.5259	0.0718	0.128*
H34B	1.4321	0.6721	0.0465	0.128*
H34C	1.3443	0.5413	−0.0067	0.128*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.060 (2)	0.061 (2)	0.148 (4)	0.0090 (18)	−0.023 (2)	0.020 (2)
O2	0.057 (2)	0.087 (3)	0.109 (3)	0.018 (2)	−0.025 (2)	−0.006 (2)
N1	0.053 (2)	0.059 (3)	0.091 (3)	0.012 (2)	−0.013 (2)	0.006 (2)
N2	0.052 (2)	0.052 (2)	0.087 (3)	0.0116 (19)	−0.018 (2)	0.003 (2)
C1	0.078 (4)	0.059 (3)	0.135 (5)	0.007 (3)	0.003 (4)	0.000 (3)
C2	0.039 (2)	0.054 (3)	0.094 (4)	0.013 (2)	−0.002 (2)	−0.002 (3)
C3	0.047 (3)	0.072 (3)	0.076 (3)	0.021 (2)	0.000 (2)	−0.004 (3)
C4	0.050 (3)	0.062 (3)	0.079 (3)	0.019 (2)	−0.011 (2)	−0.018 (3)
C5	0.047 (3)	0.060 (3)	0.075 (3)	0.015 (2)	−0.008 (2)	−0.002 (3)
C6	0.068 (3)	0.064 (3)	0.066 (3)	0.019 (3)	−0.006 (2)	−0.008 (3)
C7	0.057 (3)	0.053 (3)	0.100 (4)	0.015 (2)	−0.010 (3)	−0.017 (3)
C8	0.058 (3)	0.067 (3)	0.093 (4)	0.021 (3)	−0.016 (3)	0.004 (3)
C9	0.053 (3)	0.061 (3)	0.099 (4)	0.003 (2)	−0.003 (3)	0.004 (3)
C10	0.051 (3)	0.062 (3)	0.083 (3)	0.014 (2)	−0.005 (2)	−0.005 (3)
C11	0.046 (2)	0.065 (3)	0.070 (3)	0.012 (2)	−0.009 (2)	−0.006 (2)
C12	0.057 (3)	0.065 (3)	0.095 (4)	0.020 (3)	−0.010 (3)	−0.008 (3)
C13	0.057 (3)	0.065 (3)	0.102 (4)	0.014 (3)	−0.019 (3)	−0.015 (3)
C14	0.048 (3)	0.068 (3)	0.083 (3)	0.017 (2)	−0.011 (2)	0.000 (3)
C15	0.062 (3)	0.081 (4)	0.112 (5)	0.026 (3)	−0.014 (3)	−0.023 (3)
C16	0.053 (3)	0.075 (4)	0.096 (4)	0.016 (3)	−0.017 (3)	−0.022 (3)
C17	0.063 (4)	0.110 (5)	0.136 (6)	0.039 (4)	−0.018 (4)	−0.006 (4)
O3	0.100 (3)	0.116 (3)	0.072 (2)	0.064 (3)	−0.023 (2)	−0.017 (2)
O4	0.057 (2)	0.088 (3)	0.102 (3)	0.0357 (19)	0.0013 (19)	0.014 (2)
N3	0.043 (2)	0.072 (3)	0.075 (3)	0.0259 (19)	−0.0095 (18)	−0.007 (2)
N4	0.050 (2)	0.065 (3)	0.068 (3)	0.0202 (19)	−0.0099 (19)	−0.002 (2)
C18	0.092 (4)	0.085 (4)	0.088 (4)	0.005 (3)	−0.019 (3)	−0.004 (3)
C19	0.056 (3)	0.058 (3)	0.068 (3)	0.019 (2)	−0.009 (2)	−0.006 (2)
C20	0.040 (2)	0.071 (3)	0.073 (3)	0.012 (2)	−0.009 (2)	−0.007 (3)
C21	0.044 (2)	0.070 (3)	0.060 (3)	0.015 (2)	−0.005 (2)	−0.002 (2)
C22	0.046 (2)	0.048 (3)	0.064 (3)	0.013 (2)	0.000 (2)	−0.003 (2)
C23	0.039 (2)	0.071 (3)	0.070 (3)	0.018 (2)	−0.003 (2)	−0.001 (2)
C24	0.051 (3)	0.087 (4)	0.066 (3)	0.017 (3)	0.006 (2)	0.002 (3)
C25	0.067 (3)	0.073 (3)	0.058 (3)	0.028 (3)	−0.011 (2)	−0.006 (2)
C26	0.070 (3)	0.085 (4)	0.054 (3)	0.026 (3)	0.000 (2)	−0.010 (3)
C27	0.048 (3)	0.059 (3)	0.071 (3)	0.015 (2)	0.003 (2)	−0.010 (2)
C28	0.048 (3)	0.054 (3)	0.071 (3)	0.015 (2)	0.004 (2)	0.001 (2)
C29	0.064 (3)	0.071 (3)	0.079 (3)	0.027 (3)	0.013 (3)	0.013 (3)
C30	0.048 (3)	0.065 (3)	0.102 (4)	0.022 (2)	0.012 (3)	0.007 (3)
C31	0.050 (3)	0.054 (3)	0.076 (3)	0.017 (2)	−0.007 (2)	−0.006 (2)
C32	0.050 (3)	0.064 (3)	0.073 (3)	0.018 (2)	0.002 (2)	0.001 (2)
C33	0.046 (2)	0.059 (3)	0.067 (3)	0.014 (2)	0.000 (2)	0.000 (2)
C34	0.051 (3)	0.089 (4)	0.117 (5)	0.025 (3)	−0.005 (3)	−0.007 (3)

Geometric parameters (Å, º) top

O1—C8	1.327 (5)	O3—C25	1.325 (5)
O1—H1E	0.8500	O3—H3C	0.8200
O2—C14	1.365 (5)	O4—C31	1.382 (5)
O2—C17	1.420 (6)	O4—C34	1.423 (6)
N1—C8	1.328 (6)	N3—C25	1.329 (6)
N1—N2	1.378 (5)	N3—N4	1.374 (5)
N2—C10	1.344 (6)	N4—C27	1.355 (5)
N2—C5	1.454 (6)	N4—C22	1.407 (5)
C1—C2	1.526 (7)	C18—C19	1.502 (7)
C1—H1B	0.9600	C18—H18A	0.9600
C1—H1C	0.9600	C18—H18B	0.9600
C1—H1D	0.9600	C18—H18C	0.9600
C2—C7	1.356 (7)	C19—C20	1.372 (6)
C2—C3	1.403 (6)	C19—C24	1.395 (6)
C3—C4	1.388 (6)	C20—C21	1.372 (6)
C3—H3A	0.9300	C20—H20A	0.9300
C4—C5	1.360 (6)	C21—C22	1.388 (6)
C4—H4A	0.9300	C21—H21A	0.9300
C5—C6	1.392 (6)	C22—C23	1.391 (6)
C6—C7	1.372 (7)	C23—C24	1.346 (6)
C6—H6A	0.9300	C23—H23A	0.9300
C7—H7A	0.9300	C24—H24A	0.9300
C8—C9	1.382 (6)	C25—C26	1.413 (6)
C9—C10	1.374 (6)	C26—C27	1.344 (6)
C9—H9A	0.9300	C26—H26A	0.9300
C10—C11	1.475 (6)	C27—C28	1.480 (6)
C11—C16	1.368 (6)	C28—C29	1.386 (6)
C11—C12	1.392 (6)	C28—C33	1.389 (6)
C12—C13	1.365 (6)	C29—C30	1.382 (6)
C12—H12A	0.9300	C29—H29A	0.9300
C13—C14	1.387 (6)	C30—C31	1.356 (6)
C13—H13A	0.9300	C30—H30A	0.9300
C14—C15	1.385 (7)	C31—C32	1.384 (6)
C15—C16	1.385 (6)	C32—C33	1.379 (6)
C15—H15A	0.9300	C32—H32A	0.9300
C16—H16A	0.9300	C33—H33A	0.9300
C17—H17A	0.9600	C34—H34A	0.9600
C17—H17B	0.9600	C34—H34B	0.9600
C17—H17C	0.9600	C34—H34C	0.9600

C8—O1—H1E	118.4	C25—O3—H3C	109.5
C14—O2—C17	118.8 (4)	C31—O4—C34	116.5 (4)
C8—N1—N2	104.5 (4)	C25—N3—N4	104.2 (4)
C10—N2—N1	111.3 (4)	C27—N4—N3	111.7 (4)
C10—N2—C5	130.5 (4)	C27—N4—C22	129.9 (4)
N1—N2—C5	116.9 (4)	N3—N4—C22	118.4 (4)
C2—C1—H1B	109.5	C19—C18—H18A	109.5
C2—C1—H1C	109.5	C19—C18—H18B	109.5
H1B—C1—H1C	109.5	H18A—C18—H18B	109.5
C2—C1—H1D	109.5	C19—C18—H18C	109.5
H1B—C1—H1D	109.5	H18A—C18—H18C	109.5
H1C—C1—H1D	109.5	H18B—C18—H18C	109.5
C7—C2—C3	119.4 (5)	C20—C19—C24	116.3 (4)
C7—C2—C1	122.0 (5)	C20—C19—C18	123.2 (4)
C3—C2—C1	118.4 (5)	C24—C19—C18	120.6 (5)
C4—C3—C2	119.4 (5)	C21—C20—C19	123.8 (4)
C4—C3—H3A	120.3	C21—C20—H20A	118.1
C2—C3—H3A	120.3	C19—C20—H20A	118.1
C5—C4—C3	119.7 (5)	C20—C21—C22	118.5 (4)
C5—C4—H4A	120.1	C20—C21—H21A	120.8
C3—C4—H4A	120.1	C22—C21—H21A	120.8
C4—C5—C6	121.1 (5)	C21—C22—C23	118.5 (4)
C4—C5—N2	120.7 (4)	C21—C22—N4	120.2 (4)
C6—C5—N2	118.2 (4)	C23—C22—N4	121.3 (4)
C7—C6—C5	118.5 (5)	C24—C23—C22	121.4 (4)
C7—C6—H6A	120.8	C24—C23—H23A	119.3
C5—C6—H6A	120.8	C22—C23—H23A	119.3
C2—C7—C6	121.8 (5)	C23—C24—C19	121.5 (5)
C2—C7—H7A	119.1	C23—C24—H24A	119.2
C6—C7—H7A	119.1	C19—C24—H24A	119.2
N1—C8—O1	122.1 (4)	O3—C25—N3	122.1 (4)
N1—C8—C9	111.5 (4)	O3—C25—C26	126.8 (4)
O1—C8—C9	126.3 (5)	N3—C25—C26	110.9 (4)
C10—C9—C8	105.9 (5)	C27—C26—C25	105.9 (4)
C10—C9—H9A	127.1	C27—C26—H26A	127.0
C8—C9—H9A	127.1	C25—C26—H26A	127.0
N2—C10—C9	106.8 (4)	C26—C27—N4	107.2 (4)
N2—C10—C11	124.3 (4)	C26—C27—C28	129.7 (4)
C9—C10—C11	128.9 (5)	N4—C27—C28	123.1 (4)
C16—C11—C12	117.6 (4)	C29—C28—C33	117.1 (4)
C16—C11—C10	122.6 (4)	C29—C28—C27	121.0 (4)
C12—C11—C10	119.8 (4)	C33—C28—C27	121.9 (4)
C13—C12—C11	121.3 (5)	C30—C29—C28	122.2 (5)
C13—C12—H12A	119.3	C30—C29—H29A	118.9
C11—C12—H12A	119.3	C28—C29—H29A	118.9
C12—C13—C14	120.0 (5)	C31—C30—C29	119.2 (5)
C12—C13—H13A	120.0	C31—C30—H30A	120.4
C14—C13—H13A	120.0	C29—C30—H30A	120.4
O2—C14—C15	123.4 (5)	C30—C31—O4	125.4 (4)
O2—C14—C13	116.7 (5)	C30—C31—C32	120.7 (4)
C15—C14—C13	119.8 (4)	O4—C31—C32	114.0 (4)
C14—C15—C16	118.5 (5)	C33—C32—C31	119.5 (5)
C14—C15—H15A	120.7	C33—C32—H32A	120.2
C16—C15—H15A	120.7	C31—C32—H32A	120.2
C11—C16—C15	122.6 (5)	C32—C33—C28	121.3 (4)
C11—C16—H16A	118.7	C32—C33—H33A	119.4
C15—C16—H16A	118.7	C28—C33—H33A	119.4
O2—C17—H17A	109.5	O4—C34—H34A	109.5
O2—C17—H17B	109.5	O4—C34—H34B	109.5
H17A—C17—H17B	109.5	H34A—C34—H34B	109.5
O2—C17—H17C	109.5	O4—C34—H34C	109.5
H17A—C17—H17C	109.5	H34A—C34—H34C	109.5
H17B—C17—H17C	109.5	H34B—C34—H34C	109.5

C8—N1—N2—C10	−1.7 (6)	C25—N3—N4—C27	−2.3 (5)
C8—N1—N2—C5	−169.9 (4)	C25—N3—N4—C22	175.2 (4)
C7—C2—C3—C4	0.6 (7)	C24—C19—C20—C21	−1.4 (7)
C1—C2—C3—C4	176.4 (4)	C18—C19—C20—C21	178.9 (5)
C2—C3—C4—C5	−0.4 (7)	C19—C20—C21—C22	0.1 (7)
C3—C4—C5—C6	1.5 (7)	C20—C21—C22—C23	0.8 (7)
C3—C4—C5—N2	−176.4 (4)	C20—C21—C22—N4	−177.1 (4)
C10—N2—C5—C4	−45.2 (7)	C27—N4—C22—C21	42.1 (7)
N1—N2—C5—C4	120.3 (5)	N3—N4—C22—C21	−134.9 (4)
C10—N2—C5—C6	136.8 (5)	C27—N4—C22—C23	−135.7 (5)
N1—N2—C5—C6	−57.7 (6)	N3—N4—C22—C23	47.2 (6)
C4—C5—C6—C7	−2.7 (7)	C21—C22—C23—C24	−0.4 (7)
N2—C5—C6—C7	175.3 (4)	N4—C22—C23—C24	177.5 (4)
C3—C2—C7—C6	−2.0 (7)	C22—C23—C24—C19	−1.0 (8)
C1—C2—C7—C6	−177.5 (5)	C20—C19—C24—C23	1.8 (7)
C5—C6—C7—C2	3.0 (7)	C18—C19—C24—C23	−178.5 (5)
N2—N1—C8—O1	179.6 (5)	N4—N3—C25—O3	178.5 (4)
N2—N1—C8—C9	1.7 (6)	N4—N3—C25—C26	3.1 (5)
N1—C8—C9—C10	−1.0 (7)	O3—C25—C26—C27	−178.1 (5)
O1—C8—C9—C10	−178.9 (5)	N3—C25—C26—C27	−2.9 (6)
N1—N2—C10—C9	1.1 (6)	C25—C26—C27—N4	1.4 (6)
C5—N2—C10—C9	167.2 (5)	C25—C26—C27—C28	179.2 (5)
N1—N2—C10—C11	178.4 (4)	N3—N4—C27—C26	0.5 (5)
C5—N2—C10—C11	−15.4 (8)	C22—N4—C27—C26	−176.6 (4)
C8—C9—C10—N2	−0.1 (6)	N3—N4—C27—C28	−177.5 (4)
C8—C9—C10—C11	−177.2 (5)	C22—N4—C27—C28	5.3 (7)
N2—C10—C11—C16	−38.6 (8)	C26—C27—C28—C29	50.0 (7)
C9—C10—C11—C16	138.1 (6)	N4—C27—C28—C29	−132.4 (5)
N2—C10—C11—C12	142.9 (5)	C26—C27—C28—C33	−129.5 (6)
C9—C10—C11—C12	−40.4 (8)	N4—C27—C28—C33	48.1 (7)
C16—C11—C12—C13	−2.2 (8)	C33—C28—C29—C30	−1.1 (7)
C10—C11—C12—C13	176.3 (5)	C27—C28—C29—C30	179.4 (5)
C11—C12—C13—C14	3.2 (8)	C28—C29—C30—C31	0.7 (8)
C17—O2—C14—C15	−13.9 (8)	C29—C30—C31—O4	−179.7 (4)
C17—O2—C14—C13	163.2 (5)	C29—C30—C31—C32	0.1 (7)
C12—C13—C14—O2	179.5 (5)	C34—O4—C31—C30	−6.1 (7)
C12—C13—C14—C15	−3.4 (8)	C34—O4—C31—C32	174.2 (4)
O2—C14—C15—C16	179.5 (5)	C30—C31—C32—C33	−0.5 (7)
C13—C14—C15—C16	2.6 (8)	O4—C31—C32—C33	179.3 (4)
C12—C11—C16—C15	1.5 (8)	C31—C32—C33—C28	0.1 (7)
C10—C11—C16—C15	−177.0 (5)	C29—C28—C33—C32	0.6 (7)
C14—C15—C16—C11	−1.7 (9)	C27—C28—C33—C32	−179.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1E···N1ⁱ	0.85	1.88	2.702 (5)	164
O3—H3C···N3ⁱⁱ	0.82	1.91	2.728 (5)	175
C18—H18B···O1ⁱ	0.96	2.50	3.380 (7)	152

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆N₂O₂
M_r	280.32
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.2520 (19), 10.160 (2), 16.338 (3)
α, β, γ (°)	90.72 (3), 91.97 (3), 107.34 (3)
V (Å³)	1464.7 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.10 × 0.10

Data collection
Diffractometer	Enraf-Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.975, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	6130, 5754, 2899
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.077, 0.225, 1.09
No. of reflections	5754
No. of parameters	379
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.28

Computer programs: CAD-4 Software (Enraf-Nonius, 1985), CAD-4 Software, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1E···N1ⁱ	0.85	1.880	2.702 (5)	164.00
O3—H3C···N3ⁱⁱ	0.82	1.910	2.728 (5)	175.00
C18—H18B···O1ⁱ	0.96	2.500	3.380 (7)	152.00

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

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page