tert-Butyl 4-{[5-(4-chloro-phen-yl)-1-(4-fluoro-phen-yl)-1H-pyrazol-3-yl]carbon-yl}piperazine-1-carboxyl-ate.

In the title pyrazole derivative, C(25)H(26)ClFN(4)O(3), both benzene rings are twisted out of the plane through the pyrazole ring, with dihedral angles of 67.62 (10) and 27.63 (10)° for the fluoro- and chloro-substituted rings, respectively. The dihedral angle between the two benzene rings is 64.54 (9)°. The piperazine ring (with a chair conformation) is linked to the pyrazole ring via a carbonyl spacer and is orientated to lie to one side of the pyrazole plane. In addition to an intra-molecular C-H⋯N contact, there are inter-molecular C-H⋯O inter-actions, which generate a supra-molecular chain with an undulating topology along the c axis that is sustained by alternating centrosymmetric ten-membered {⋯HCNCO}(2) and {⋯HC3O}(2) synthons.

Related literature

For the pharmacological potential of pyrazol derivatives, see: Ragavan et al. (2009 ▶). For the synthesis, see: Ragavan et al. (2010 ▶). For a related structure, see: Samshuddin et al. (2010 ▶).

Experimental

Crystal data

C25H26ClFN4O3

M = 484.95

Triclinic,

a = 6.0568 (5) Å

b = 12.0047 (10) Å

c = 16.2615 (13) Å

α = 88.852 (1)°

β = 81.206 (1)°

γ = 87.644 (1)°

V = 1167.37 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.21 mm−1

T = 100 K

0.35 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: analytical (FACES; Bruker, 2009 ▶) T min = 0.931, T max = 0.980

11213 measured reflections

5318 independent reflections

4351 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.145

S = 1.06

5318 reflections

310 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.39 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: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038560/hb5646sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038560/hb5646Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C25H26ClFN4O3	Z = 2
Mr = 484.95	F(000) = 508
Triclinic, P1	Dx = 1.380 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0568 (5) Å	Cell parameters from 3796 reflections
b = 12.0047 (10) Å	θ = 3.0–30.6°
c = 16.2615 (13) Å	µ = 0.21 mm−1
α = 88.852 (1)°	T = 100 K
β = 81.206 (1)°	Block, colourless
γ = 87.644 (1)°	0.35 × 0.10 × 0.10 mm
V = 1167.37 (17) Å3

Bruker SMART APEX diffractometer	5318 independent reflections
Radiation source: fine-focus sealed tube	4351 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω scan	θmax = 27.5°, θmin = 2.1°
Absorption correction: analytical (FACES; Bruker, 2009)	h = −7→7
Tmin = 0.931, Tmax = 0.980	k = −15→15
11213 measured reflections	l = −21→21

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0829P)2 + 0.4102P] where P = (Fo2 + 2Fc2)/3
5318 reflections	(Δ/σ)max = 0.001
310 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
Cl1	−0.54699 (8)	0.35562 (4)	0.36749 (3)	0.02774 (15)
F1	−0.3361 (2)	0.60200 (11)	0.83637 (8)	0.0351 (3)
O1	0.6767 (2)	−0.00368 (11)	0.59753 (8)	0.0216 (3)
O2	0.6127 (2)	−0.13676 (12)	1.00046 (8)	0.0223 (3)
O3	0.9285 (2)	−0.21367 (11)	0.92542 (8)	0.0186 (3)
N1	0.1504 (2)	0.26137 (12)	0.66173 (9)	0.0155 (3)
N2	0.3142 (2)	0.20929 (13)	0.69823 (10)	0.0167 (3)
N3	0.6639 (2)	0.04516 (13)	0.73200 (9)	0.0150 (3)
N4	0.6836 (3)	−0.11496 (14)	0.86022 (10)	0.0202 (3)
C1	0.0220 (3)	0.35009 (14)	0.70660 (10)	0.0148 (3)
C2	0.1251 (3)	0.44859 (15)	0.71731 (11)	0.0174 (4)
H2	0.2778	0.4572	0.6948	0.021*
C3	0.0030 (3)	0.53487 (16)	0.76141 (12)	0.0225 (4)
H3	0.0699	0.6033	0.7692	0.027*
C4	−0.2166 (3)	0.51834 (17)	0.79337 (12)	0.0226 (4)
C5	−0.3210 (3)	0.42072 (17)	0.78344 (12)	0.0213 (4)
H5	−0.4732	0.4122	0.8067	0.026*
C6	−0.2004 (3)	0.33534 (16)	0.73909 (11)	0.0183 (4)
H6	−0.2690	0.2675	0.7310	0.022*
C7	−0.0359 (3)	0.25317 (15)	0.53333 (11)	0.0154 (4)
C8	−0.1139 (3)	0.36381 (15)	0.52973 (11)	0.0180 (4)
H8	−0.0618	0.4178	0.5634	0.022*
C9	−0.2670 (3)	0.39586 (16)	0.47737 (12)	0.0199 (4)
H9	−0.3181	0.4715	0.4747	0.024*
C10	−0.3444 (3)	0.31675 (16)	0.42920 (11)	0.0183 (4)
C11	−0.2662 (3)	0.20696 (16)	0.43007 (12)	0.0212 (4)
H11	−0.3183	0.1535	0.3960	0.025*
C12	−0.1106 (3)	0.17607 (16)	0.48145 (11)	0.0188 (4)
H12	−0.0536	0.1011	0.4814	0.023*
C13	0.1254 (3)	0.21355 (14)	0.58746 (11)	0.0147 (3)
C14	0.2801 (3)	0.12616 (15)	0.57692 (11)	0.0166 (4)
H14	0.3060	0.0757	0.5319	0.020*
C15	0.3920 (3)	0.12677 (14)	0.64627 (11)	0.0150 (3)
C16	0.5851 (3)	0.04965 (14)	0.65783 (11)	0.0149 (3)
C17	0.5275 (3)	0.06276 (15)	0.81360 (11)	0.0168 (4)
H17A	0.3856	0.1031	0.8066	0.020*
H17B	0.6083	0.1087	0.8482	0.020*
C18	0.4778 (3)	−0.04902 (16)	0.85671 (12)	0.0194 (4)
H18A	0.3988	−0.0365	0.9139	0.023*
H18B	0.3788	−0.0904	0.8261	0.023*
C19	0.8221 (3)	−0.13264 (16)	0.77930 (11)	0.0190 (4)
H19A	0.7429	−0.1786	0.7441	0.023*
H19B	0.9640	−0.1726	0.7869	0.023*
C20	0.8709 (3)	−0.02034 (16)	0.73720 (11)	0.0180 (4)
H20A	0.9664	0.0214	0.7690	0.022*
H20B	0.9537	−0.0320	0.6805	0.022*
C21	0.7328 (3)	−0.15410 (15)	0.93439 (11)	0.0165 (4)
C22	1.0055 (3)	−0.26720 (16)	0.99898 (11)	0.0191 (4)
C23	1.2187 (3)	−0.32815 (17)	0.96125 (13)	0.0250 (4)
H23A	1.1842	−0.3848	0.9231	0.038*
H23B	1.2900	−0.3642	1.0056	0.038*
H23C	1.3205	−0.2750	0.9306	0.038*
C24	0.8349 (3)	−0.34893 (18)	1.03985 (14)	0.0285 (5)
H24A	0.7967	−0.3989	0.9977	0.043*
H24B	0.6998	−0.3076	1.0655	0.043*
H24C	0.8984	−0.3928	1.0826	0.043*
C25	1.0532 (3)	−0.17857 (18)	1.05902 (12)	0.0236 (4)
H25A	1.1630	−0.1278	1.0301	0.035*
H25B	1.1128	−0.2146	1.1061	0.035*
H25C	0.9145	−0.1363	1.0795	0.035*

	U11	U22	U33	U12	U13	U23
Cl1	0.0254 (3)	0.0297 (3)	0.0319 (3)	−0.0024 (2)	−0.0172 (2)	0.0069 (2)
F1	0.0380 (7)	0.0319 (7)	0.0337 (7)	0.0169 (6)	−0.0032 (6)	−0.0137 (6)
O1	0.0250 (7)	0.0246 (7)	0.0150 (6)	0.0078 (6)	−0.0038 (5)	−0.0048 (5)
O2	0.0206 (7)	0.0289 (7)	0.0157 (7)	0.0027 (5)	0.0011 (5)	0.0025 (6)
O3	0.0179 (6)	0.0224 (7)	0.0154 (6)	0.0036 (5)	−0.0036 (5)	0.0020 (5)
N1	0.0174 (7)	0.0153 (7)	0.0146 (7)	0.0012 (6)	−0.0054 (6)	0.0004 (6)
N2	0.0159 (7)	0.0155 (7)	0.0192 (8)	0.0029 (6)	−0.0057 (6)	0.0019 (6)
N3	0.0150 (7)	0.0178 (7)	0.0117 (7)	0.0035 (6)	−0.0017 (5)	0.0005 (6)
N4	0.0211 (8)	0.0230 (8)	0.0148 (7)	0.0073 (6)	−0.0001 (6)	0.0034 (6)
C1	0.0170 (8)	0.0150 (8)	0.0123 (8)	0.0057 (6)	−0.0037 (6)	−0.0006 (6)
C2	0.0180 (8)	0.0198 (9)	0.0147 (8)	−0.0006 (7)	−0.0031 (7)	0.0003 (7)
C3	0.0299 (10)	0.0169 (9)	0.0221 (9)	0.0012 (8)	−0.0090 (8)	−0.0037 (7)
C4	0.0274 (10)	0.0216 (10)	0.0185 (9)	0.0107 (8)	−0.0049 (8)	−0.0044 (7)
C5	0.0173 (9)	0.0276 (10)	0.0182 (9)	0.0042 (7)	−0.0018 (7)	0.0011 (8)
C6	0.0197 (9)	0.0179 (9)	0.0178 (9)	0.0005 (7)	−0.0043 (7)	0.0002 (7)
C7	0.0141 (8)	0.0172 (9)	0.0145 (8)	0.0000 (6)	−0.0015 (6)	0.0024 (7)
C8	0.0202 (9)	0.0176 (9)	0.0166 (8)	−0.0001 (7)	−0.0040 (7)	−0.0003 (7)
C9	0.0211 (9)	0.0193 (9)	0.0194 (9)	0.0007 (7)	−0.0043 (7)	0.0024 (7)
C10	0.0150 (8)	0.0245 (10)	0.0157 (8)	0.0009 (7)	−0.0048 (7)	0.0044 (7)
C11	0.0236 (9)	0.0215 (10)	0.0203 (9)	−0.0035 (7)	−0.0083 (7)	−0.0007 (7)
C12	0.0226 (9)	0.0185 (9)	0.0153 (8)	0.0005 (7)	−0.0037 (7)	0.0007 (7)
C13	0.0161 (8)	0.0147 (8)	0.0134 (8)	−0.0002 (6)	−0.0023 (6)	−0.0005 (6)
C14	0.0185 (8)	0.0160 (9)	0.0155 (8)	−0.0010 (7)	−0.0033 (7)	0.0002 (7)
C15	0.0160 (8)	0.0127 (8)	0.0162 (8)	0.0017 (6)	−0.0028 (7)	0.0000 (7)
C16	0.0159 (8)	0.0139 (8)	0.0148 (8)	−0.0005 (6)	−0.0019 (6)	0.0005 (7)
C17	0.0184 (8)	0.0183 (9)	0.0126 (8)	0.0042 (7)	−0.0004 (7)	−0.0016 (7)
C18	0.0167 (8)	0.0233 (10)	0.0169 (9)	0.0040 (7)	−0.0008 (7)	0.0039 (7)
C19	0.0210 (9)	0.0204 (9)	0.0141 (8)	0.0087 (7)	−0.0006 (7)	−0.0021 (7)
C20	0.0142 (8)	0.0243 (10)	0.0152 (8)	0.0043 (7)	−0.0024 (7)	0.0013 (7)
C21	0.0160 (8)	0.0139 (8)	0.0199 (9)	0.0003 (6)	−0.0039 (7)	0.0001 (7)
C22	0.0194 (9)	0.0220 (9)	0.0167 (9)	0.0008 (7)	−0.0061 (7)	0.0041 (7)
C23	0.0226 (10)	0.0252 (10)	0.0276 (10)	0.0059 (8)	−0.0070 (8)	0.0011 (8)
C24	0.0262 (10)	0.0279 (11)	0.0319 (11)	−0.0026 (8)	−0.0070 (9)	0.0127 (9)
C25	0.0196 (9)	0.0335 (11)	0.0175 (9)	0.0018 (8)	−0.0030 (7)	−0.0020 (8)

Cl1—C10	1.7439 (18)	C9—H9	0.9500
F1—C4	1.355 (2)	C10—C11	1.383 (3)
O1—C16	1.228 (2)	C11—C12	1.387 (2)
O2—C21	1.218 (2)	C11—H11	0.9500
O3—C21	1.349 (2)	C12—H12	0.9500
O3—C22	1.475 (2)	C13—C14	1.373 (2)
N1—N2	1.357 (2)	C14—C15	1.402 (2)
N1—C13	1.379 (2)	C14—H14	0.9500
N1—C1	1.436 (2)	C15—C16	1.494 (2)
N2—C15	1.338 (2)	C17—C18	1.521 (3)
N3—C16	1.363 (2)	C17—H17A	0.9900
N3—C20	1.465 (2)	C17—H17B	0.9900
N3—C17	1.466 (2)	C18—H18A	0.9900
N4—C21	1.356 (2)	C18—H18B	0.9900
N4—C18	1.457 (2)	C19—C20	1.519 (3)
N4—C19	1.463 (2)	C19—H19A	0.9900
C1—C6	1.387 (3)	C19—H19B	0.9900
C1—C2	1.386 (2)	C20—H20A	0.9900
C2—C3	1.392 (3)	C20—H20B	0.9900
C2—H2	0.9500	C22—C23	1.509 (3)
C3—C4	1.373 (3)	C22—C24	1.523 (3)
C3—H3	0.9500	C22—C25	1.524 (3)
C4—C5	1.378 (3)	C23—H23A	0.9800
C5—C6	1.382 (3)	C23—H23B	0.9800
C5—H5	0.9500	C23—H23C	0.9800
C6—H6	0.9500	C24—H24A	0.9800
C7—C8	1.394 (3)	C24—H24B	0.9800
C7—C12	1.398 (2)	C24—H24C	0.9800
C7—C13	1.471 (2)	C25—H25A	0.9800
C8—C9	1.390 (2)	C25—H25B	0.9800
C8—H8	0.9500	C25—H25C	0.9800
C9—C10	1.384 (3)
C21—O3—C22	119.64 (14)	C14—C15—C16	124.05 (16)
N2—N1—C13	112.50 (14)	O1—C16—N3	121.74 (16)
N2—N1—C1	117.44 (14)	O1—C16—C15	118.02 (15)
C13—N1—C1	129.91 (14)	N3—C16—C15	120.11 (15)
C15—N2—N1	104.23 (14)	N3—C17—C18	109.81 (14)
C16—N3—C20	118.19 (14)	N3—C17—H17A	109.7
C16—N3—C17	125.08 (14)	C18—C17—H17A	109.7
C20—N3—C17	112.72 (14)	N3—C17—H17B	109.7
C21—N4—C18	120.10 (15)	C18—C17—H17B	109.7
C21—N4—C19	125.57 (15)	H17A—C17—H17B	108.2
C18—N4—C19	114.33 (14)	N4—C18—C17	110.80 (15)
C6—C1—C2	121.44 (16)	N4—C18—H18A	109.5
C6—C1—N1	119.72 (16)	C17—C18—H18A	109.5
C2—C1—N1	118.84 (16)	N4—C18—H18B	109.5
C1—C2—C3	119.41 (17)	C17—C18—H18B	109.5
C1—C2—H2	120.3	H18A—C18—H18B	108.1
C3—C2—H2	120.3	N4—C19—C20	109.09 (15)
C4—C3—C2	118.21 (18)	N4—C19—H19A	109.9
C4—C3—H3	120.9	C20—C19—H19A	109.9
C2—C3—H3	120.9	N4—C19—H19B	109.9
F1—C4—C3	118.44 (18)	C20—C19—H19B	109.9
F1—C4—C5	118.57 (18)	H19A—C19—H19B	108.3
C3—C4—C5	122.99 (18)	N3—C20—C19	111.15 (14)
C4—C5—C6	118.84 (18)	N3—C20—H20A	109.4
C4—C5—H5	120.6	C19—C20—H20A	109.4
C6—C5—H5	120.6	N3—C20—H20B	109.4
C5—C6—C1	119.12 (17)	C19—C20—H20B	109.4
C5—C6—H6	120.4	H20A—C20—H20B	108.0
C1—C6—H6	120.4	O2—C21—O3	124.94 (16)
C8—C7—C12	118.48 (16)	O2—C21—N4	123.32 (17)
C8—C7—C13	123.44 (16)	O3—C21—N4	111.74 (15)
C12—C7—C13	118.06 (16)	O3—C22—C23	102.28 (14)
C9—C8—C7	120.63 (17)	O3—C22—C24	110.27 (15)
C9—C8—H8	119.7	C23—C22—C24	110.76 (17)
C7—C8—H8	119.7	O3—C22—C25	109.96 (15)
C10—C9—C8	119.52 (17)	C23—C22—C25	110.84 (16)
C10—C9—H9	120.2	C24—C22—C25	112.29 (17)
C8—C9—H9	120.2	C22—C23—H23A	109.5
C11—C10—C9	121.10 (16)	C22—C23—H23B	109.5
C11—C10—Cl1	119.40 (14)	H23A—C23—H23B	109.5
C9—C10—Cl1	119.49 (14)	C22—C23—H23C	109.5
C10—C11—C12	118.99 (17)	H23A—C23—H23C	109.5
C10—C11—H11	120.5	H23B—C23—H23C	109.5
C12—C11—H11	120.5	C22—C24—H24A	109.5
C11—C12—C7	121.22 (17)	C22—C24—H24B	109.5
C11—C12—H12	119.4	H24A—C24—H24B	109.5
C7—C12—H12	119.4	C22—C24—H24C	109.5
C14—C13—N1	105.62 (15)	H24A—C24—H24C	109.5
C14—C13—C7	129.58 (16)	H24B—C24—H24C	109.5
N1—C13—C7	124.79 (16)	C22—C25—H25A	109.5
C13—C14—C15	105.83 (16)	C22—C25—H25B	109.5
C13—C14—H14	127.1	H25A—C25—H25B	109.5
C15—C14—H14	127.1	C22—C25—H25C	109.5
N2—C15—C14	111.80 (15)	H25A—C25—H25C	109.5
N2—C15—C16	124.02 (15)	H25B—C25—H25C	109.5
C13—N1—N2—C15	−0.52 (19)	N1—C13—C14—C15	−0.33 (19)
C1—N1—N2—C15	175.46 (15)	C7—C13—C14—C15	179.05 (17)
N2—N1—C1—C6	−110.40 (18)	N1—N2—C15—C14	0.29 (19)
C13—N1—C1—C6	64.8 (2)	N1—N2—C15—C16	176.34 (16)
N2—N1—C1—C2	68.8 (2)	C13—C14—C15—N2	0.0 (2)
C13—N1—C1—C2	−116.1 (2)	C13—C14—C15—C16	−176.02 (16)
C6—C1—C2—C3	−0.2 (3)	C20—N3—C16—O1	3.6 (3)
N1—C1—C2—C3	−179.36 (16)	C17—N3—C16—O1	−152.18 (17)
C1—C2—C3—C4	0.5 (3)	C20—N3—C16—C15	−172.10 (15)
C2—C3—C4—F1	179.97 (16)	C17—N3—C16—C15	32.1 (2)
C2—C3—C4—C5	−0.3 (3)	N2—C15—C16—O1	−162.19 (17)
F1—C4—C5—C6	179.53 (16)	C14—C15—C16—O1	13.4 (3)
C3—C4—C5—C6	−0.3 (3)	N2—C15—C16—N3	13.6 (3)
C4—C5—C6—C1	0.5 (3)	C14—C15—C16—N3	−170.78 (16)
C2—C1—C6—C5	−0.3 (3)	C16—N3—C17—C18	101.11 (19)
N1—C1—C6—C5	178.85 (15)	C20—N3—C17—C18	−55.79 (19)
C12—C7—C8—C9	1.7 (3)	C21—N4—C18—C17	124.53 (18)
C13—C7—C8—C9	−179.81 (17)	C19—N4—C18—C17	−55.4 (2)
C7—C8—C9—C10	0.8 (3)	N3—C17—C18—N4	53.54 (19)
C8—C9—C10—C11	−2.3 (3)	C21—N4—C19—C20	−124.91 (19)
C8—C9—C10—Cl1	176.78 (14)	C18—N4—C19—C20	55.0 (2)
C9—C10—C11—C12	1.2 (3)	C16—N3—C20—C19	−101.57 (18)
Cl1—C10—C11—C12	−177.88 (14)	C17—N3—C20—C19	57.07 (19)
C10—C11—C12—C7	1.4 (3)	N4—C19—C20—N3	−54.33 (19)
C8—C7—C12—C11	−2.9 (3)	C22—O3—C21—O2	2.6 (3)
C13—C7—C12—C11	178.60 (17)	C22—O3—C21—N4	−177.38 (15)
N2—N1—C13—C14	0.5 (2)	C18—N4—C21—O2	−0.3 (3)
C1—N1—C13—C14	−174.80 (17)	C19—N4—C21—O2	179.57 (17)
N2—N1—C13—C7	−178.88 (16)	C18—N4—C21—O3	179.63 (15)
C1—N1—C13—C7	5.8 (3)	C19—N4—C21—O3	−0.5 (3)
C8—C7—C13—C14	−151.42 (19)	C21—O3—C22—C23	177.25 (15)
C12—C7—C13—C14	27.0 (3)	C21—O3—C22—C24	59.4 (2)
C8—C7—C13—N1	27.9 (3)	C21—O3—C22—C25	−64.9 (2)
C12—C7—C13—N1	−153.69 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17a···N2	0.99	2.24	2.950 (2)	128
C14—H14···O1i	0.95	2.28	3.192 (2)	161
C18—H18a···O2ii	0.99	2.52	3.223 (2)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17a⋯N2	0.99	2.24	2.950 (2)	128
C14—H14⋯O1i	0.95	2.28	3.192 (2)	161
C18—H18a⋯O2ii	0.99	2.52	3.223 (2)	128

Symmetry codes: (i) ; (ii) .