1-Cyclo­hexyl-5-(4-meth­oxy­phen­yl)-1H-pyrazole-4-carb­oxy­lic acid

Fun, H.-K.; Quah, C.K.; Chandrakantha, B.; Isloor, A.M.; Shetty, P.

doi:10.1107/S1600536811050872

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3513

https://doi.org/10.1107/S1600536811050872

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1-Cyclohexyl-5-(4-methoxyphenyl)-1H-pyrazole-4-carboxylic acid

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § B. Chandrakantha,^b A. M. Isloor ^c and Prakash Shetty ^d

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Chemistry, Manipal Institute of Technology, Manipal 576 104, India, ^cMedicinal Chemistry Division, Department of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India, and ^dDepartment of Printing, Manipal Institute of Technology, Manipal 576 104, India
^*Correspondence e-mail: hkfun@usm.my

(Received 25 November 2011; accepted 26 November 2011; online 30 November 2011)

In the title compound, C₁₇H₂₀N₂O₃, the methoxyphenyl unit is disordered over two sets of sites in a 0.715 (4):0.285 (4) ratio. The pyrazole ring forms dihedral angles of 55.88 (16) and 72.6 (4)° with the benzene rings of its major and minor components, respectively. The cyclohexane ring adopts a chair conformation and its C—N bond is in an equatorial orientation. In the crystal, molecules are linked into inversion dimers by pairs of O—H⋯O hydrogen bonds, generating R₂²(8) loops.

Related literature

For bond-length data, see: Allen et al. (1987 ). For related structures and medicinal background to pyrazole derivatives, see: Fun et al. (2010a ,b , 2011 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For ring conformations, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₇H₂₀N₂O₃
M_r = 300.35
Monoclinic, P 2₁ /c
a = 12.0722 (9) Å
b = 12.7180 (9) Å
c = 11.7739 (8) Å
β = 118.698 (1)°
V = 1585.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.39 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.967, T_max = 0.987
24474 measured reflections
4585 independent reflections
2766 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.159
S = 1.03
4585 reflections
239 parameters
17 restraints
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O1ⁱ	0.91	1.73	2.640 (2)	174
Symmetry code: (i) -x, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811050872/hb6534sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811050872/hb6534Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811050872/hb6534Isup3.cml

checkCIF report

Comment top

As part of our ongoing structural studies of pyrazole derivatives (Fun et al., 2010a, 2010b), we now describe the synthesis and structure of the title compound, (I).

The molecular structure is shown in Fig. 1. The methoxy phenyl moiety (O3/C4-C9/C17) is disordered over two sets of sites with refined site occupancies of 0.715 (4): 0.285 (4). The pyrazole ring (N1/N2/C1-C3) forms dihedral angles of 55.88 (16) and 72.6 (4)° with the benzene rings (C4-C9) of major and minor components of the methoxy phenyl moiety, respectively. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Fun et al., 2010a, 2010b, 2011). The cyclohexane ring (C10-C15) adopts a chair conformation with puckering parameters (Cremer & Pople, 1975) Q = 0.571 (2) Å, Θ = 1.0 (2)° and φ = 300 (19)°.

In the crystal (Fig. 2), molecules are linked into inversion dimers by pairs of O2–H1O2···O1 hydrogen bonds (Table 1), generating eight-membered R²₂(8) ring motifs (Bernstein et al., 1995).

Related literature top

For bond-length data, see: Allen et al. (1987). For related structures and medicinal background to pyrazole derivatives, see: Fun et al. (2010a,b, 2011). For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring conformations, see: Cremer & Pople (1975).

Experimental top

A mixture of ethyl-3-(dimethylamino)-2-(4-methoxy phenylcarbonyl) prop-2-enoate (2.0g, 0.0088 mol) and cyclohexyl hydrazine (1.0 g, 0.0096 mol) in absolute ethanol (20 ml) was refluxed for 2h. On cooling, the separated colorless needle-shaped crystals of 5-(4-methoxy phenyl)-1-phenyl-1H-pyrazole-4- carboxylic acid ethyl ester were collected by filtration (yield: 2.0 g, 86%, m.p.: 390-395K). To a stirred solution of ester (1.0 g, 0.0031 mol) in THF with water (1:1, 20 ml) was added lithium hydroxide (0.26 g, 0.0062 mol) and the mixture was stirred at RT for 6h. The reaction mixture was concentrated and acidified with 10% citric acid solution. The solid that separated out was filtered and dried under high vacuum to afford title compound as colorless crystalline solid. Compound was recrystallized from methanol to yield colourless needles (yield: 1.5 g, 83%, m.p. 413-418K).

Structure description top

As part of our ongoing structural studies of pyrazole derivatives (Fun et al., 2010a, 2010b), we now describe the synthesis and structure of the title compound, (I).

In the crystal (Fig. 2), molecules are linked into inversion dimers by pairs of O2–H1O2···O1 hydrogen bonds (Table 1), generating eight-membered R²₂(8) ring motifs (Bernstein et al., 1995).

For bond-length data, see: Allen et al. (1987). For related structures and medicinal background to pyrazole derivatives, see: Fun et al. (2010a,b, 2011). For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring conformations, see: Cremer & Pople (1975).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids for non-H atoms. Both major and minor components of disorder are shown.
	Fig. 2. The crystal structure of the major component of the title compound, viewed along the a axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

1-Cyclohexyl-5-(4-methoxyphenyl)-1H-pyrazole-4-carboxylic acid top

Crystal data top

C₁₇H₂₀N₂O₃	F(000) = 640
M_r = 300.35	D_x = 1.258 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5000 reflections
a = 12.0722 (9) Å	θ = 2.5–29.8°
b = 12.7180 (9) Å	µ = 0.09 mm⁻¹
c = 11.7739 (8) Å	T = 296 K
β = 118.698 (1)°	Needle, colourless
V = 1585.6 (2) Å³	0.39 × 0.20 × 0.15 mm
Z = 4

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	4585 independent reflections
Radiation source: fine-focus sealed tube	2766 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
φ and ω scans	θ_max = 29.9°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→16
T_min = 0.967, T_max = 0.987	k = −17→17
24474 measured reflections	l = −16→16

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0614P)² + 0.3536P] where P = (F_o² + 2F_c²)/3
4585 reflections	(Δ/σ)_max = 0.001
239 parameters	Δρ_max = 0.21 e Å⁻³
17 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₇H₂₀N₂O₃	V = 1585.6 (2) Å³
M_r = 300.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.0722 (9) Å	µ = 0.09 mm⁻¹
b = 12.7180 (9) Å	T = 296 K
c = 11.7739 (8) Å	0.39 × 0.20 × 0.15 mm
β = 118.698 (1)°

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	4585 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2766 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.987	R_int = 0.049
24474 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	17 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.03	Δρ_max = 0.21 e Å⁻³
4585 reflections	Δρ_min = −0.28 e Å⁻³
239 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
O1	0.07405 (12)	0.45236 (14)	0.92263 (12)	0.0870 (5)
O2	0.15254 (12)	0.47797 (13)	1.13352 (11)	0.0814 (5)
H1O2	0.0749	0.4999	1.1195	0.122*
O3A	0.1055 (2)	0.39532 (19)	0.44671 (17)	0.0769 (8)	0.715 (4)
C4A	0.2726 (5)	0.3627 (5)	0.8457 (5)	0.0409 (10)	0.715 (4)
C5A	0.1549 (3)	0.3174 (3)	0.7674 (3)	0.0528 (7)	0.715 (4)
H5AA	0.1137	0.2823	0.8057	0.063*	0.715 (4)
C6A	0.0978 (4)	0.3237 (3)	0.6330 (3)	0.0573 (9)	0.715 (4)
H6AA	0.0206	0.2909	0.5820	0.069*	0.715 (4)
C7A	0.1563 (3)	0.3787 (3)	0.5760 (2)	0.0489 (6)	0.715 (4)
C8A	0.2749 (3)	0.4202 (2)	0.6523 (3)	0.0523 (7)	0.715 (4)
H8AA	0.3168	0.4540	0.6139	0.063*	0.715 (4)
C9A	0.3314 (3)	0.4121 (2)	0.7843 (3)	0.0453 (6)	0.715 (4)
H9AA	0.4115	0.4405	0.8341	0.054*	0.715 (4)
C17A	−0.0253 (3)	0.3757 (3)	0.3667 (3)	0.0861 (11)	0.715 (4)
H17A	−0.0504	0.3991	0.2802	0.129*	0.715 (4)
H17B	−0.0727	0.4129	0.3999	0.129*	0.715 (4)
H17C	−0.0413	0.3016	0.3657	0.129*	0.715 (4)
O3B	0.0427 (5)	0.3332 (4)	0.4351 (5)	0.0707 (18)*	0.285 (4)
C4B	0.2589 (16)	0.3476 (14)	0.8323 (13)	0.043 (3)*	0.285 (4)
C5B	0.1646 (8)	0.2768 (6)	0.7716 (8)	0.051 (2)*	0.285 (4)
H5B	0.1475	0.2291	0.8211	0.061*	0.285 (4)
C6	0.0940 (9)	0.2735 (8)	0.6402 (9)	0.059 (2)	0.285 (4)
H6B	0.0277	0.2259	0.6006	0.070*	0.285 (4)
C7B	0.1219 (7)	0.3407 (6)	0.5680 (7)	0.0456 (18)*	0.285 (4)
C8B	0.2195 (9)	0.4113 (7)	0.6240 (8)	0.060 (2)*	0.285 (4)
H8B	0.2389	0.4551	0.5727	0.072*	0.285 (4)
C9B	0.2888 (8)	0.4168 (8)	0.7578 (9)	0.062 (3)*	0.285 (4)
H9B	0.3539	0.4654	0.7976	0.074*	0.285 (4)
C17B	0.0494 (10)	0.4149 (7)	0.3569 (10)	0.092 (3)*	0.285 (4)
H17D	−0.0130	0.4034	0.2684	0.138*	0.285 (4)
H17E	0.1319	0.4157	0.3637	0.138*	0.285 (4)
H17F	0.0338	0.4812	0.3857	0.138*	0.285 (4)
N1	0.44673 (12)	0.32694 (11)	1.06351 (12)	0.0524 (3)
N2	0.48284 (13)	0.34101 (14)	1.19163 (13)	0.0676 (4)
C1	0.38353 (16)	0.38444 (16)	1.19118 (16)	0.0650 (5)
H1A	0.3804	0.4035	1.2658	0.078*
C2	0.28347 (14)	0.39865 (14)	1.06610 (15)	0.0525 (4)
C3	0.32756 (13)	0.36065 (13)	0.98426 (14)	0.0460 (3)
C10	0.53239 (13)	0.27005 (13)	1.02944 (15)	0.0482 (4)
H10A	0.4887	0.2600	0.9354	0.058*
C11	0.56252 (17)	0.16218 (14)	1.09219 (18)	0.0602 (4)
H11A	0.4849	0.1227	1.0639	0.072*
H11B	0.6021	0.1698	1.1855	0.072*
C12	0.65043 (16)	0.10250 (14)	1.05635 (18)	0.0620 (5)
H12A	0.6723	0.0355	1.1013	0.074*
H12B	0.6072	0.0884	0.9640	0.074*
C13	0.76923 (16)	0.16370 (16)	1.0912 (2)	0.0734 (6)
H13A	0.8210	0.1254	1.0628	0.088*
H13B	0.8171	0.1715	1.1845	0.088*
C14	0.73834 (17)	0.27110 (16)	1.0285 (2)	0.0730 (6)
H14A	0.6976	0.2632	0.9351	0.088*
H14B	0.8159	0.3103	1.0555	0.088*
C15	0.65178 (16)	0.33218 (14)	1.0652 (2)	0.0622 (5)
H15A	0.6952	0.3460	1.1575	0.075*
H15B	0.6302	0.3992	1.0203	0.075*
C16	0.16128 (15)	0.44458 (16)	1.03370 (16)	0.0589 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0572 (7)	0.1573 (15)	0.0477 (7)	0.0425 (8)	0.0262 (6)	0.0055 (8)
O2	0.0613 (7)	0.1362 (13)	0.0527 (7)	0.0334 (8)	0.0323 (6)	−0.0050 (7)
O3A	0.0761 (14)	0.1104 (18)	0.0383 (10)	0.0057 (13)	0.0227 (9)	0.0049 (10)
C4A	0.0356 (19)	0.051 (2)	0.0423 (17)	0.0014 (13)	0.0234 (14)	−0.0032 (16)
C5A	0.0468 (14)	0.068 (2)	0.0531 (15)	−0.0086 (15)	0.0315 (12)	−0.0019 (14)
C6A	0.0447 (14)	0.077 (2)	0.0497 (16)	−0.0107 (18)	0.0226 (12)	−0.0097 (17)
C7A	0.0523 (16)	0.0575 (17)	0.0399 (13)	0.0057 (14)	0.0246 (12)	0.0014 (12)
C8A	0.0507 (16)	0.0666 (16)	0.0485 (14)	0.0042 (13)	0.0308 (13)	0.0101 (11)
C9A	0.0399 (14)	0.0515 (14)	0.0479 (14)	0.0012 (12)	0.0237 (12)	0.0039 (10)
C17A	0.0647 (18)	0.121 (3)	0.0512 (16)	0.0264 (19)	0.0110 (14)	−0.0099 (16)
C6	0.047 (4)	0.073 (6)	0.059 (4)	−0.013 (4)	0.027 (3)	−0.003 (4)
N1	0.0429 (7)	0.0684 (9)	0.0456 (7)	0.0084 (6)	0.0212 (6)	−0.0078 (6)
N2	0.0543 (8)	0.0971 (12)	0.0453 (8)	0.0182 (8)	0.0190 (6)	−0.0117 (7)
C1	0.0571 (10)	0.0919 (14)	0.0469 (9)	0.0174 (9)	0.0257 (8)	−0.0064 (9)
C2	0.0466 (8)	0.0704 (10)	0.0457 (8)	0.0107 (7)	0.0261 (7)	0.0011 (7)
C3	0.0401 (7)	0.0557 (9)	0.0461 (8)	0.0029 (6)	0.0238 (6)	0.0001 (6)
C10	0.0380 (7)	0.0575 (9)	0.0505 (8)	0.0035 (6)	0.0224 (6)	−0.0086 (7)
C11	0.0566 (9)	0.0603 (10)	0.0690 (11)	0.0006 (8)	0.0344 (9)	−0.0028 (8)
C12	0.0566 (10)	0.0564 (10)	0.0689 (11)	0.0086 (8)	0.0268 (9)	−0.0059 (8)
C13	0.0450 (9)	0.0802 (13)	0.0877 (14)	0.0097 (9)	0.0259 (9)	−0.0166 (11)
C14	0.0508 (9)	0.0802 (13)	0.1005 (15)	−0.0074 (9)	0.0463 (10)	−0.0130 (11)
C15	0.0515 (9)	0.0560 (10)	0.0826 (13)	−0.0032 (7)	0.0351 (9)	−0.0106 (9)
C16	0.0501 (9)	0.0872 (13)	0.0474 (9)	0.0161 (8)	0.0297 (8)	0.0036 (8)

Geometric parameters (Å, º) top

O1—C16	1.227 (2)	C8B—H8B	0.9300
O2—C16	1.3007 (19)	C9B—H9B	0.9300
O2—H1O2	0.9133	C17B—H17D	0.9600
O3A—C7A	1.357 (3)	C17B—H17E	0.9600
O3A—C17A	1.419 (4)	C17B—H17F	0.9600
C4A—C9A	1.384 (4)	N1—C3	1.3546 (19)
C4A—C5A	1.394 (5)	N1—N2	1.3660 (18)
C4A—C3	1.436 (5)	N1—C10	1.4671 (18)
C5A—C6A	1.393 (4)	N2—C1	1.318 (2)
C5A—H5AA	0.9300	C1—C2	1.397 (2)
C6A—C7A	1.376 (4)	C1—H1A	0.9300
C6A—H6AA	0.9300	C2—C3	1.392 (2)
C7A—C8A	1.379 (4)	C2—C16	1.457 (2)
C8A—C9A	1.368 (4)	C10—C15	1.515 (2)
C8A—H8AA	0.9300	C10—C11	1.517 (2)
C9A—H9AA	0.9300	C10—H10A	0.9800
C17A—H17A	0.9600	C11—C12	1.520 (2)
C17A—H17B	0.9600	C11—H11A	0.9700
C17A—H17C	0.9600	C11—H11B	0.9700
O3B—C7B	1.391 (8)	C12—C13	1.505 (3)
O3B—C17B	1.416 (10)	C12—H12A	0.9700
C4B—C5B	1.355 (12)	C12—H12B	0.9700
C4B—C9B	1.407 (13)	C13—C14	1.512 (3)
C4B—C3	1.578 (14)	C13—H13A	0.9700
C5B—C6	1.363 (10)	C13—H13B	0.9700
C5B—H5B	0.9300	C14—C15	1.521 (2)
C6—C7B	1.358 (10)	C14—H14A	0.9700
C6—H6B	0.9300	C14—H14B	0.9700
C7B—C8B	1.373 (9)	C15—H15A	0.9700
C8B—C9B	1.386 (10)	C15—H15B	0.9700

C16—O2—H1O2	117.2	N2—C1—H1A	123.7
C7A—O3A—C17A	118.5 (3)	C2—C1—H1A	123.7
C9A—C4A—C5A	117.3 (4)	C3—C2—C1	105.08 (14)
C9A—C4A—C3	121.9 (4)	C3—C2—C16	129.32 (15)
C5A—C4A—C3	120.8 (3)	C1—C2—C16	125.60 (15)
C6A—C5A—C4A	121.2 (3)	N1—C3—C2	105.40 (13)
C6A—C5A—H5AA	119.4	N1—C3—C4A	123.2 (3)
C4A—C5A—H5AA	119.4	C2—C3—C4A	131.2 (3)
C7A—C6A—C5A	119.6 (3)	N1—C3—C4B	123.6 (8)
C7A—C6A—H6AA	120.2	C2—C3—C4B	130.8 (8)
C5A—C6A—H6AA	120.2	N1—C10—C15	111.61 (13)
O3A—C7A—C6A	124.4 (3)	N1—C10—C11	110.39 (13)
O3A—C7A—C8A	116.1 (3)	C15—C10—C11	111.26 (13)
C6A—C7A—C8A	119.5 (2)	N1—C10—H10A	107.8
C9A—C8A—C7A	120.4 (2)	C15—C10—H10A	107.8
C9A—C8A—H8AA	119.8	C11—C10—H10A	107.8
C7A—C8A—H8AA	119.8	C10—C11—C12	110.64 (15)
C8A—C9A—C4A	121.8 (3)	C10—C11—H11A	109.5
C8A—C9A—H9AA	119.1	C12—C11—H11A	109.5
C4A—C9A—H9AA	119.1	C10—C11—H11B	109.5
C7B—O3B—C17B	117.3 (7)	C12—C11—H11B	109.5
C5B—C4B—C9B	119.3 (11)	H11A—C11—H11B	108.1
C5B—C4B—C3	121.2 (9)	C13—C12—C11	111.52 (15)
C9B—C4B—C3	119.3 (9)	C13—C12—H12A	109.3
C4B—C5B—C6	121.9 (9)	C11—C12—H12A	109.3
C4B—C5B—H5B	119.0	C13—C12—H12B	109.3
C6—C5B—H5B	119.0	C11—C12—H12B	109.3
C7B—C6—C5B	118.9 (8)	H12A—C12—H12B	108.0
C7B—C6—H6B	120.5	C12—C13—C14	110.78 (15)
C5B—C6—H6B	120.5	C12—C13—H13A	109.5
C6—C7B—C8B	121.7 (7)	C14—C13—H13A	109.5
C6—C7B—O3B	114.7 (7)	C12—C13—H13B	109.5
C8B—C7B—O3B	123.6 (7)	C14—C13—H13B	109.5
C7B—C8B—C9B	119.3 (8)	H13A—C13—H13B	108.1
C7B—C8B—H8B	120.3	C13—C14—C15	111.37 (17)
C9B—C8B—H8B	120.3	C13—C14—H14A	109.4
C8B—C9B—C4B	118.8 (9)	C15—C14—H14A	109.4
C8B—C9B—H9B	120.6	C13—C14—H14B	109.4
C4B—C9B—H9B	120.6	C15—C14—H14B	109.4
O3B—C17B—H17D	109.5	H14A—C14—H14B	108.0
O3B—C17B—H17E	109.5	C10—C15—C14	110.26 (14)
H17D—C17B—H17E	109.5	C10—C15—H15A	109.6
O3B—C17B—H17F	109.5	C14—C15—H15A	109.6
H17D—C17B—H17F	109.5	C10—C15—H15B	109.6
H17E—C17B—H17F	109.5	C14—C15—H15B	109.6
C3—N1—N2	112.92 (12)	H15A—C15—H15B	108.1
C3—N1—C10	128.51 (13)	O1—C16—O2	122.41 (15)
N2—N1—C10	118.26 (12)	O1—C16—C2	123.66 (15)
C1—N2—N1	104.07 (13)	O2—C16—C2	113.93 (14)
N2—C1—C2	112.52 (15)

C9A—C4A—C5A—C6A	−1.4 (8)	C1—C2—C3—N1	0.32 (19)
C3—C4A—C5A—C6A	176.6 (4)	C16—C2—C3—N1	179.92 (18)
C4A—C5A—C6A—C7A	−2.3 (6)	C1—C2—C3—C4A	−173.6 (3)
C17A—O3A—C7A—C6A	14.3 (4)	C16—C2—C3—C4A	6.0 (4)
C17A—O3A—C7A—C8A	−166.1 (3)	C1—C2—C3—C4B	175.8 (7)
C5A—C6A—C7A—O3A	−175.6 (3)	C16—C2—C3—C4B	−4.6 (7)
C5A—C6A—C7A—C8A	4.8 (5)	C9A—C4A—C3—N1	−53.1 (7)
O3A—C7A—C8A—C9A	176.7 (2)	C5A—C4A—C3—N1	129.0 (5)
C6A—C7A—C8A—C9A	−3.6 (4)	C9A—C4A—C3—C2	119.9 (5)
C7A—C8A—C9A—C4A	−0.1 (5)	C5A—C4A—C3—C2	−58.0 (7)
C5A—C4A—C9A—C8A	2.6 (7)	C9A—C4A—C3—C4B	−149 (8)
C3—C4A—C9A—C8A	−175.4 (4)	C5A—C4A—C3—C4B	33 (7)
C9B—C4B—C5B—C6	−3 (2)	C5B—C4B—C3—N1	107.3 (15)
C3—C4B—C5B—C6	171.7 (11)	C9B—C4B—C3—N1	−78.2 (17)
C4B—C5B—C6—C7B	2.3 (17)	C5B—C4B—C3—C2	−67.5 (19)
C5B—C6—C7B—C8B	0.3 (14)	C9B—C4B—C3—C2	107.0 (14)
C5B—C6—C7B—O3B	−178.5 (8)	C5B—C4B—C3—C4A	−163 (9)
C17B—O3B—C7B—C6	166.9 (8)	C9B—C4B—C3—C4A	11 (6)
C17B—O3B—C7B—C8B	−11.8 (12)	C3—N1—C10—C15	118.83 (18)
C6—C7B—C8B—C9B	−2.2 (14)	N2—N1—C10—C15	−68.1 (2)
O3B—C7B—C8B—C9B	176.4 (7)	C3—N1—C10—C11	−116.88 (18)
C7B—C8B—C9B—C4B	1.6 (16)	N2—N1—C10—C11	56.22 (19)
C5B—C4B—C9B—C8B	1 (2)	N1—C10—C11—C12	179.54 (13)
C3—C4B—C9B—C8B	−173.8 (11)	C15—C10—C11—C12	−55.96 (19)
C3—N1—N2—C1	0.0 (2)	C10—C11—C12—C13	55.8 (2)
C10—N1—N2—C1	−174.16 (16)	C11—C12—C13—C14	−56.0 (2)
N1—N2—C1—C2	0.2 (2)	C12—C13—C14—C15	56.4 (2)
N2—C1—C2—C3	−0.4 (2)	N1—C10—C15—C14	−179.95 (15)
N2—C1—C2—C16	−179.98 (19)	C11—C10—C15—C14	56.3 (2)
N2—N1—C3—C2	−0.20 (19)	C13—C14—C15—C10	−56.4 (2)
C10—N1—C3—C2	173.21 (16)	C3—C2—C16—O1	3.2 (3)
N2—N1—C3—C4A	174.3 (3)	C1—C2—C16—O1	−177.3 (2)
C10—N1—C3—C4A	−12.2 (4)	C3—C2—C16—O2	−176.26 (18)
N2—N1—C3—C4B	−176.1 (6)	C1—C2—C16—O2	3.3 (3)
C10—N1—C3—C4B	−2.7 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1ⁱ	0.91	1.73	2.640 (2)	174

Symmetry code: (i) −x, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₀N₂O₃
M_r	300.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.0722 (9), 12.7180 (9), 11.7739 (8)
β (°)	118.698 (1)
V (Å³)	1585.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.39 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.967, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	24474, 4585, 2766
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.702

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.159, 1.03
No. of reflections	4585
No. of parameters	239
No. of restraints	17
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.28

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1ⁱ	0.91	1.73	2.640 (2)	174

Symmetry code: (i) −x, −y+1, −z+2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

HKF and CKQ thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). AMI thanks the Board for Research in Nuclear Sciences, Department of Atomic Energy, Government of India for the Young Scientist award.

References

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