1-(Furan-2-yl)-2-(2H-indazol-2-yl)ethanone.

The asymmetric unit of the title compound, C13H10N2O2, contains two crystallographically independent mol-ecules (A and B). The indazole ring systems are approximately planar [maximum deviations = 0.0037 (15) and -0.0198 (15) Å], and their mean planes are oriented at 80.10 (5) and 65.97 (4)° with respect to the furan rings in mol-ecules A and B, respectively. In the crystal, pairs of C-H⋯N hydrogen bonds link the B mol-ecules, forming inversion dimers. These dimers are bridged by the A mol-ecules via C-H⋯O hydrogen bonds, forming sheets parallel to (011). There are also C-H⋯π inter-actions present, and π-π inter-actions between neighbouring furan and the indazole rings [centroid-centroid distance = 3.8708 (9) Å] of inversion-related mol-ecules, forming a three-dimensional structure.

Related literature

For related structures, see: Peeters et al. (1979 ▶); Freer et al. (1986 ▶); Özel Güven et al. (2008a ▶,b ▶, 2013 ▶, 2014 ▶).

Experimental

Crystal data

C13H10N2O2

M = 226.23

Triclinic,

a = 9.2899 (3) Å

b = 10.6863 (4) Å

c = 11.7826 (5) Å

α = 77.046 (3)°

β = 70.780 (3)°

γ = 88.930 (4)°

V = 1074.47 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 294 K

0.17 × 0.15 × 0.10 mm

Data collection

Rigaku Saturn724+ diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2011 ▶) T min = 0.984, T max = 0.990

10517 measured reflections

5256 independent reflections

4130 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.127

S = 1.14

5256 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CrystalClear (Rigaku, 2011 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814006606/su2716sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814006606/su2716Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814006606/su2716Isup3.cml

CCDC reference: 993569

Additional supporting information: crystallographic information; 3D view; checkCIF report

C13H10N2O2	Z = 4
Mr = 226.23	F(000) = 472
Triclinic, P1	Dx = 1.399 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2899 (3) Å	Cell parameters from 9141 reflections
b = 10.6863 (4) Å	θ = 3.0–28.7°
c = 11.7826 (5) Å	µ = 0.10 mm−1
α = 77.046 (3)°	T = 294 K
β = 70.780 (3)°	Block, colourless
γ = 88.930 (4)°	0.17 × 0.15 × 0.10 mm
V = 1074.47 (7) Å3

Rigaku Saturn724+ diffractometer	5256 independent reflections
Radiation source: fine-focus sealed tube	4130 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω scans	θmax = 28.7°, θmin = 3.0°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2011)	h = −12→11
Tmin = 0.984, Tmax = 0.990	k = −14→14
10517 measured reflections	l = −15→15

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0629P)2 + 0.1259P] where P = (Fo2 + 2Fc2)/3
5256 reflections	(Δ/σ)max < 0.001
307 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.34655 (12)	0.40513 (9)	0.72286 (9)	0.0301 (2)
O2	0.12038 (12)	0.66910 (9)	0.67289 (10)	0.0306 (2)
N1	0.13004 (13)	0.35998 (10)	0.95859 (10)	0.0222 (2)
N2	0.22341 (13)	0.35403 (11)	1.02685 (10)	0.0240 (3)
C1	0.24816 (16)	0.48234 (12)	0.74176 (12)	0.0227 (3)
C2	0.23765 (16)	0.58932 (12)	0.64362 (13)	0.0238 (3)
C3	0.32561 (18)	0.63034 (14)	0.52231 (13)	0.0295 (3)
H3	0.4122	0.5936	0.4795	0.035*
C4	0.2570 (2)	0.74121 (15)	0.47503 (14)	0.0356 (4)
H4	0.2902	0.7910	0.3945	0.043*
C5	0.13524 (19)	0.76044 (14)	0.56853 (15)	0.0358 (4)
H5	0.0703	0.8270	0.5625	0.043*
C6	0.13153 (16)	0.47746 (12)	0.86879 (12)	0.0236 (3)
H6A	0.1536	0.5500	0.8986	0.028*
H6B	0.0307	0.4862	0.8613	0.028*
C7	0.03917 (15)	0.25281 (12)	0.98598 (12)	0.0228 (3)
H7	−0.0318	0.2389	0.9492	0.027*
C8	0.07307 (15)	0.16724 (12)	1.08045 (12)	0.0220 (3)
C9	0.02026 (16)	0.04070 (13)	1.15061 (13)	0.0267 (3)
H9	−0.0550	−0.0043	1.1372	0.032*
C10	0.08333 (17)	−0.01324 (13)	1.23873 (14)	0.0297 (3)
H10	0.0501	−0.0961	1.2859	0.036*
C11	0.19855 (18)	0.05475 (14)	1.25960 (14)	0.0302 (3)
H11	0.2388	0.0151	1.3203	0.036*
C12	0.25205 (17)	0.17660 (13)	1.19336 (13)	0.0263 (3)
H12	0.3278	0.2199	1.2079	0.032*
C13	0.18851 (15)	0.23470 (12)	1.10204 (12)	0.0221 (3)
O1'	0.12771 (11)	0.65903 (9)	0.22019 (9)	0.0277 (2)
O2'	0.12290 (11)	0.46552 (9)	0.41588 (8)	0.0256 (2)
N1'	0.36805 (13)	0.72809 (11)	0.00180 (10)	0.0221 (2)
N2'	0.36774 (13)	0.71328 (10)	−0.10991 (10)	0.0215 (2)
C1'	0.23839 (15)	0.59371 (12)	0.21100 (12)	0.0212 (3)
C2'	0.24799 (15)	0.48921 (12)	0.31045 (11)	0.0210 (3)
C3'	0.35788 (16)	0.40672 (12)	0.32360 (12)	0.0238 (3)
H3'	0.4531	0.4032	0.2654	0.029*
C4'	0.29694 (18)	0.32704 (13)	0.44471 (13)	0.0281 (3)
H4'	0.3444	0.2603	0.4814	0.034*
C5'	0.15650 (17)	0.36727 (13)	0.49609 (13)	0.0270 (3)
H5'	0.0917	0.3321	0.5759	0.032*
C6'	0.37597 (16)	0.61447 (13)	0.09316 (12)	0.0252 (3)
H6C	0.4680	0.6225	0.1133	0.030*
H6D	0.3827	0.5397	0.0582	0.030*
C7'	0.36543 (16)	0.85057 (13)	0.01246 (12)	0.0238 (3)
H7'	0.3641	0.8792	0.0817	0.029*
C8'	0.36502 (15)	0.92660 (12)	−0.10033 (12)	0.0214 (3)
C9'	0.36551 (15)	1.05980 (13)	−0.15096 (12)	0.0242 (3)
H9'	0.3624	1.1197	−0.1039	0.029*
C10'	0.37064 (16)	1.09798 (13)	−0.27098 (13)	0.0264 (3)
H10'	0.3718	1.1852	−0.3060	0.032*
C11'	0.37424 (17)	1.00751 (13)	−0.34351 (12)	0.0267 (3)
H11'	0.3779	1.0372	−0.4249	0.032*
C12'	0.37248 (16)	0.87798 (12)	−0.29719 (12)	0.0236 (3)
H12'	0.3747	0.8196	−0.3455	0.028*
C13'	0.36711 (15)	0.83599 (12)	−0.17304 (12)	0.0201 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0299 (6)	0.0234 (5)	0.0321 (6)	0.0032 (4)	−0.0042 (4)	−0.0062 (4)
O2	0.0290 (6)	0.0273 (5)	0.0327 (6)	0.0029 (4)	−0.0084 (4)	−0.0044 (4)
N1	0.0198 (6)	0.0240 (5)	0.0223 (6)	−0.0006 (4)	−0.0066 (4)	−0.0047 (4)
N2	0.0224 (6)	0.0257 (6)	0.0248 (6)	−0.0011 (5)	−0.0091 (5)	−0.0057 (5)
C1	0.0226 (7)	0.0200 (6)	0.0248 (7)	−0.0029 (5)	−0.0065 (5)	−0.0056 (5)
C2	0.0238 (7)	0.0217 (6)	0.0266 (7)	0.0010 (5)	−0.0080 (6)	−0.0076 (5)
C3	0.0294 (8)	0.0318 (7)	0.0267 (7)	−0.0066 (6)	−0.0045 (6)	−0.0118 (6)
C4	0.0491 (10)	0.0320 (8)	0.0268 (8)	−0.0105 (7)	−0.0180 (7)	0.0002 (6)
C5	0.0393 (9)	0.0277 (7)	0.0426 (9)	0.0008 (6)	−0.0216 (8)	−0.0003 (6)
C6	0.0228 (7)	0.0220 (6)	0.0238 (7)	0.0001 (5)	−0.0059 (5)	−0.0038 (5)
C7	0.0186 (6)	0.0255 (7)	0.0242 (7)	−0.0013 (5)	−0.0061 (5)	−0.0068 (5)
C8	0.0184 (6)	0.0239 (6)	0.0225 (6)	−0.0008 (5)	−0.0044 (5)	−0.0065 (5)
C9	0.0232 (7)	0.0247 (7)	0.0297 (7)	−0.0031 (5)	−0.0055 (6)	−0.0058 (5)
C10	0.0306 (8)	0.0229 (7)	0.0304 (7)	−0.0006 (6)	−0.0066 (6)	−0.0011 (5)
C11	0.0320 (8)	0.0302 (7)	0.0293 (8)	0.0051 (6)	−0.0128 (6)	−0.0049 (6)
C12	0.0246 (7)	0.0281 (7)	0.0283 (7)	0.0006 (5)	−0.0113 (6)	−0.0069 (6)
C13	0.0207 (6)	0.0219 (6)	0.0220 (6)	−0.0002 (5)	−0.0049 (5)	−0.0049 (5)
O1'	0.0231 (5)	0.0331 (5)	0.0226 (5)	0.0041 (4)	−0.0050 (4)	−0.0017 (4)
O2'	0.0238 (5)	0.0299 (5)	0.0177 (5)	−0.0005 (4)	−0.0031 (4)	−0.0005 (4)
N1'	0.0214 (6)	0.0248 (6)	0.0168 (5)	−0.0008 (4)	−0.0037 (4)	−0.0021 (4)
N2'	0.0216 (6)	0.0241 (5)	0.0169 (5)	−0.0010 (4)	−0.0044 (4)	−0.0040 (4)
C1'	0.0207 (7)	0.0247 (6)	0.0190 (6)	−0.0004 (5)	−0.0072 (5)	−0.0053 (5)
C2'	0.0213 (6)	0.0244 (6)	0.0157 (6)	−0.0019 (5)	−0.0044 (5)	−0.0039 (5)
C3'	0.0264 (7)	0.0249 (6)	0.0201 (6)	0.0009 (5)	−0.0075 (5)	−0.0057 (5)
C4'	0.0378 (8)	0.0242 (7)	0.0237 (7)	0.0020 (6)	−0.0138 (6)	−0.0025 (5)
C5'	0.0319 (8)	0.0259 (7)	0.0200 (6)	−0.0035 (6)	−0.0083 (6)	0.0008 (5)
C6'	0.0225 (7)	0.0276 (7)	0.0204 (6)	0.0028 (5)	−0.0041 (5)	−0.0004 (5)
C7'	0.0232 (7)	0.0282 (7)	0.0201 (6)	−0.0022 (5)	−0.0058 (5)	−0.0075 (5)
C8'	0.0187 (6)	0.0238 (6)	0.0206 (6)	−0.0016 (5)	−0.0040 (5)	−0.0064 (5)
C9'	0.0219 (7)	0.0242 (6)	0.0255 (7)	−0.0017 (5)	−0.0038 (5)	−0.0099 (5)
C10'	0.0260 (7)	0.0209 (6)	0.0271 (7)	−0.0010 (5)	−0.0040 (6)	−0.0025 (5)
C11'	0.0303 (7)	0.0265 (7)	0.0199 (7)	0.0007 (6)	−0.0061 (6)	−0.0018 (5)
C12'	0.0272 (7)	0.0236 (6)	0.0200 (6)	−0.0008 (5)	−0.0069 (5)	−0.0060 (5)
C13'	0.0180 (6)	0.0210 (6)	0.0198 (6)	−0.0012 (5)	−0.0045 (5)	−0.0045 (5)

O1—C1	1.2190 (17)	O1'—C1'	1.2207 (16)
O2—C2	1.3720 (17)	O2'—C2'	1.3701 (16)
O2—C5	1.3562 (18)	O2'—C5'	1.3528 (16)
N1—N2	1.3556 (15)	N1'—C6'	1.4496 (16)
N1—C6	1.4462 (16)	N1'—C7'	1.3417 (17)
N1—C7	1.3488 (16)	N2'—N1'	1.3614 (15)
N2—C13	1.3550 (16)	N2'—C13'	1.3559 (16)
C1—C2	1.4598 (18)	C1'—C6'	1.5214 (18)
C1—C6	1.5219 (19)	C2'—C1'	1.4514 (18)
C2—C3	1.366 (2)	C2'—C3'	1.3610 (19)
C3—C4	1.425 (2)	C3'—C4'	1.4223 (19)
C3—H3	0.9300	C3'—H3'	0.9300
C4—C5	1.344 (2)	C4'—H4'	0.9300
C4—H4	0.9300	C5'—C4'	1.353 (2)
C5—H5	0.9300	C5'—H5'	0.9300
C6—H6A	0.9700	C6'—H6C	0.9700
C6—H6B	0.9700	C6'—H6D	0.9700
C7—H7	0.9300	C7'—H7'	0.9300
C8—C7	1.3922 (19)	C8'—C7'	1.3948 (18)
C8—C9	1.4174 (18)	C9'—C8'	1.4141 (18)
C9—H9	0.9300	C9'—C10'	1.3660 (19)
C10—C9	1.369 (2)	C9'—H9'	0.9300
C10—C11	1.420 (2)	C10'—C11'	1.4202 (19)
C10—H10	0.9300	C10'—H10'	0.9300
C11—H11	0.9300	C11'—H11'	0.9300
C12—C11	1.3655 (19)	C12'—C11'	1.3675 (18)
C12—H12	0.9300	C12'—C13'	1.4150 (18)
C13—C8	1.4231 (18)	C12'—H12'	0.9300
C13—C12	1.4130 (19)	C13'—C8'	1.4255 (18)
C5—O2—C2	106.78 (12)	C5'—O2'—C2'	106.24 (11)
N2—N1—C6	119.17 (10)	N2'—N1'—C6'	118.38 (11)
C7—N1—N2	114.56 (11)	C7'—N1'—N2'	114.33 (11)
C7—N1—C6	126.24 (11)	C7'—N1'—C6'	127.26 (11)
C13—N2—N1	103.11 (10)	C13'—N2'—N1'	102.97 (10)
O1—C1—C2	121.81 (13)	O1'—C1'—C2'	122.77 (12)
O1—C1—C6	122.96 (12)	O1'—C1'—C6'	122.35 (11)
C2—C1—C6	115.20 (12)	C2'—C1'—C6'	114.88 (12)
O2—C2—C1	117.61 (12)	O2'—C2'—C1'	115.92 (12)
C3—C2—O2	109.94 (12)	C3'—C2'—O2'	110.48 (11)
C3—C2—C1	132.44 (14)	C3'—C2'—C1'	133.60 (12)
C2—C3—C4	105.59 (14)	C2'—C3'—C4'	105.77 (13)
C2—C3—H3	127.2	C2'—C3'—H3'	127.1
C4—C3—H3	127.2	C4'—C3'—H3'	127.1
C3—C4—H4	126.4	O2'—C5'—H5'	124.5
C5—C4—C3	107.20 (13)	C4'—C5'—O2'	110.93 (12)
C5—C4—H4	126.4	C4'—C5'—H5'	124.5
O2—C5—H5	124.8	C3'—C4'—H4'	126.7
C4—C5—O2	110.48 (14)	C5'—C4'—C3'	106.58 (13)
C4—C5—H5	124.8	C5'—C4'—H4'	126.7
N1—C6—C1	113.33 (11)	N1'—C6'—C1'	112.61 (11)
N1—C6—H6A	108.9	N1'—C6'—H6C	109.1
N1—C6—H6B	108.9	N1'—C6'—H6D	109.1
C1—C6—H6A	108.9	C1'—C6'—H6C	109.1
C1—C6—H6B	108.9	C1'—C6'—H6D	109.1
H6A—C6—H6B	107.7	H6C—C6'—H6D	107.8
N1—C7—C8	106.09 (11)	N1'—C7'—C8'	106.76 (11)
N1—C7—H7	127.0	N1'—C7'—H7'	126.6
C8—C7—H7	127.0	C8'—C7'—H7'	126.6
C7—C8—C9	135.26 (13)	C7'—C8'—C9'	135.85 (12)
C7—C8—C13	104.46 (11)	C7'—C8'—C13'	103.89 (11)
C9—C8—C13	120.28 (12)	C9'—C8'—C13'	120.25 (12)
C8—C9—H9	121.0	C8'—C9'—H9'	121.0
C10—C9—C8	118.01 (13)	C10'—C9'—C8'	118.06 (12)
C10—C9—H9	121.0	C10'—C9'—H9'	121.0
C9—C10—C11	121.33 (13)	C9'—C10'—C11'	121.52 (12)
C9—C10—H10	119.3	C9'—C10'—H10'	119.2
C11—C10—H10	119.3	C11'—C10'—H10'	119.2
C10—C11—H11	119.0	C10'—C11'—H11'	119.0
C12—C11—C10	122.04 (13)	C12'—C11'—C10'	121.97 (12)
C12—C11—H11	119.0	C12'—C11'—H11'	119.0
C11—C12—C13	117.78 (13)	C11'—C12'—C13'	117.58 (12)
C11—C12—H12	121.1	C11'—C12'—H12'	121.2
C13—C12—H12	121.1	C13'—C12'—H12'	121.2
N2—C13—C8	111.78 (12)	N2'—C13'—C8'	112.04 (11)
N2—C13—C12	127.66 (12)	N2'—C13'—C12'	127.32 (12)
C12—C13—C8	120.56 (12)	C12'—C13'—C8'	120.61 (11)
C5—O2—C2—C1	179.45 (12)	C5'—O2'—C2'—C1'	−179.04 (11)
C5—O2—C2—C3	0.22 (15)	C5'—O2'—C2'—C3'	0.50 (14)
C2—O2—C5—C4	0.01 (16)	C2'—O2'—C5'—C4'	−0.84 (15)
C6—N1—N2—C13	177.98 (11)	N2'—N1'—C6'—C1'	−119.87 (13)
C7—N1—N2—C13	0.09 (15)	C7'—N1'—C6'—C1'	62.35 (18)
N2—N1—C6—C1	89.29 (14)	N2'—N1'—C7'—C8'	−0.71 (16)
C7—N1—C6—C1	−93.08 (15)	C6'—N1'—C7'—C8'	177.15 (12)
N2—N1—C7—C8	0.11 (16)	C13'—N2'—N1'—C6'	−177.16 (11)
C6—N1—C7—C8	−177.61 (12)	C13'—N2'—N1'—C7'	0.91 (15)
N1—N2—C13—C8	−0.25 (15)	N1'—N2'—C13'—C8'	−0.76 (14)
N1—N2—C13—C12	−179.97 (14)	N1'—N2'—C13'—C12'	177.36 (13)
O1—C1—C2—O2	178.16 (12)	O1'—C1'—C6'—N1'	7.19 (18)
O1—C1—C2—C3	−2.8 (2)	C2'—C1'—C6'—N1'	−173.78 (11)
C6—C1—C2—O2	−3.81 (17)	O2'—C2'—C1'—O1'	1.42 (19)
C6—C1—C2—C3	175.21 (14)	O2'—C2'—C1'—C6'	−177.60 (11)
O1—C1—C6—N1	−11.17 (18)	C3'—C2'—C1'—O1'	−177.99 (14)
C2—C1—C6—N1	170.83 (11)	C3'—C2'—C1'—C6'	3.0 (2)
O2—C2—C3—C4	−0.35 (15)	O2'—C2'—C3'—C4'	0.00 (15)
C1—C2—C3—C4	−179.43 (14)	C1'—C2'—C3'—C4'	179.43 (14)
C2—C3—C4—C5	0.35 (16)	C2'—C3'—C4'—C5'	−0.50 (15)
C3—C4—C5—O2	−0.22 (17)	O2'—C5'—C4'—C3'	0.85 (16)
C9—C8—C7—N1	179.74 (15)	C9'—C8'—C7'—N1'	−178.62 (15)
C13—C8—C7—N1	−0.25 (15)	C13'—C8'—C7'—N1'	0.19 (15)
C7—C8—C9—C10	−179.87 (16)	C10'—C9'—C8'—C7'	177.57 (15)
C13—C8—C9—C10	0.1 (2)	C10'—C9'—C8'—C13'	−1.1 (2)
C11—C10—C9—C8	−0.2 (2)	C8'—C9'—C10'—C11'	0.5 (2)
C9—C10—C11—C12	0.0 (2)	C9'—C10'—C11'—C12'	0.1 (2)
C13—C12—C11—C10	0.2 (2)	C13'—C12'—C11'—C10'	−0.1 (2)
N2—C13—C8—C7	0.32 (16)	C11'—C12'—C13'—N2'	−178.52 (13)
N2—C13—C8—C9	−179.67 (12)	C11'—C12'—C13'—C8'	−0.5 (2)
C12—C13—C8—C7	−179.94 (13)	N2'—C13'—C8'—C7'	0.38 (15)
C12—C13—C8—C9	0.1 (2)	N2'—C13'—C8'—C9'	179.41 (12)
N2—C13—C12—C11	179.48 (14)	C12'—C13'—C8'—C7'	−177.89 (12)
C8—C13—C12—C11	−0.2 (2)	C12'—C13'—C8'—C9'	1.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3′—H3′···N2′i	0.93	2.57	3.4031 (18)	149
C7—H7···O1′ii	0.93	2.48	3.2544 (17)	141
C10′—H10′···O1iii	0.93	2.44	3.2719 (17)	148
C7—H7···Cg5iv	0.93	2.97	3.6000 (16)	126
C9—H9···Cg6iv	0.93	2.81	3.4312 (17)	125
C9′—H9′···Cg2v	0.93	2.94	3.6743 (15)	137
C12′—H12′···Cg1i	0.93	2.63	3.4480 (16)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg5 and Cg6 are the centroids of the O2/C2–C5, N1/N2/C7/C8/C13, N1′/N2′/C7′/C8′/C13′, and C8′–C13′ rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3′—H3′⋯N2′i	0.93	2.57	3.4031 (18)	149
C7—H7⋯O1′ii	0.93	2.48	3.2544 (17)	141
C10′—H10′⋯O1iii	0.93	2.44	3.2719 (17)	148
C7—H7⋯Cg5iv	0.93	2.97	3.6000 (16)	126
C9—H9⋯Cg6iv	0.93	2.81	3.4312 (17)	125
C9′—H9′⋯Cg2v	0.93	2.94	3.6743 (15)	137
C12′—H12′⋯Cg1i	0.93	2.63	3.4480 (16)	147

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .