A 1:2 cocrystal of genistein with isonicotinamide: crystal structure and Hirshfeld surface analysis

Sowa, M.; Ślepokura, K.; Matczak-Jon, E.

doi:10.1107/S0108270113029545

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A 1:2 cocrystal of genistein with isonicotinamide: crystal structure and Hirshfeld surface analysis

M. Sowa, K. Slepokura and E. Matczak-Jon

Genistein, a naturally occurring polyphenolic compound, was combined with isonicotinamide, a pharmaceutically acceptable coformer, to yield a 1:2 cocrystal [systematic name: 5,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one-pyridine-4-carboxamide (1/2)], C₁₅H₁₀O₅·2C₆H₆N₂O. The molecules in the cocrystalline phase are present in their neutral forms, and assemble a molecular layer by means of hydrogen bonding.

Keywords: crystal structure; flavonoids; cocrystals; active pharmaceutical ingredients; genistein; Hirshfeld surface analysis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113029545/fm3012sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270113029545/fm3012Isup2.hkl Contains datablock I
	MDL mol file https://doi.org/10.1107/S0108270113029545/fm3012Isup3.mol Supplementary material

CCDC reference: 968754

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2010); cell refinement: CrysAlis RED (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009) and (DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008).

5,7-Dihydroxy-3-(4-hydroxyphenyl)chromen-4-one–pyridine-4-carboxamide (1/2) top

Crystal data top

C₁₅H₁₀O₅·2C₆H₆N₂O	Z = 2
M_r = 514.48	F(000) = 536
Triclinic, P1	D_x = 1.472 Mg m⁻³
a = 8.233 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.872 (4) Å	Cell parameters from 6644 reflections
c = 13.773 (4) Å	θ = 3.0–36.7°
α = 109.61 (3)°	µ = 0.11 mm⁻¹
β = 95.34 (3)°	T = 120 K
γ = 109.75 (3)°	Block, yellow
V = 1160.7 (7) Å³	0.28 × 0.20 × 0.13 mm

Data collection top

Kuma KM4-CCD kappa-geometry diffractometer with a Sapphire 2 CCD camera	4659 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	R_int = 0.033
ω scans	θ_max = 36.8°, θ_min = 3.0°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	h = −10→13
T_min = 0.797, T_max = 1.000	k = −15→13
12982 measured reflections	l = −23→18
6651 independent reflections

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)] = 0.055	Hydrogen site location: difference Fourier map
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.095P)²] where P = (F_o² + 2F_c²)/3
6651 reflections	(Δ/σ)_max < 0.001
371 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

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	0.51834 (13)	0.12381 (11)	0.64558 (8)	0.0209 (2)
O4	0.89729 (14)	0.23163 (11)	0.48528 (8)	0.0229 (2)
O5	1.08861 (14)	0.14973 (12)	0.57897 (9)	0.0251 (2)
H5	1.042 (3)	0.184 (2)	0.5331 (19)	0.057 (7)*
O7	0.84395 (15)	−0.04517 (11)	0.81085 (8)	0.0227 (2)
H7	0.942 (4)	−0.070 (3)	0.809 (2)	0.070 (8)*
O14	0.52340 (16)	0.52997 (11)	0.30225 (9)	0.0238 (2)
H14	0.411 (3)	0.510 (2)	0.2813 (19)	0.056 (7)*
C2	0.5048 (2)	0.19105 (15)	0.58482 (11)	0.0202 (3)
H2	0.4026	0.2110	0.5800	0.024*
C3	0.62496 (18)	0.23205 (14)	0.53057 (10)	0.0173 (3)
C4	0.78245 (18)	0.20255 (14)	0.53669 (10)	0.0175 (3)
C5	0.95471 (19)	0.11236 (15)	0.62600 (11)	0.0189 (3)
C6	0.97093 (19)	0.05227 (15)	0.69395 (11)	0.0204 (3)
H6	1.0741	0.0353	0.7063	0.024*
C7	0.83373 (19)	0.01619 (14)	0.74491 (11)	0.0189 (3)
C8	0.68226 (19)	0.04062 (15)	0.72878 (11)	0.0195 (3)
H8	0.5904	0.0167	0.7640	0.023*
C9	0.66908 (18)	0.10083 (14)	0.65992 (10)	0.0176 (3)
C10	0.80092 (18)	0.13788 (14)	0.60627 (10)	0.0162 (3)
C11	0.59631 (19)	0.30788 (14)	0.46906 (11)	0.0186 (3)
C12	0.42640 (19)	0.28361 (15)	0.41736 (11)	0.0192 (3)
H12	0.3271	0.2156	0.4201	0.023*
C13	0.39942 (19)	0.35676 (15)	0.36201 (11)	0.0202 (3)
H13	0.2827	0.3380	0.3270	0.024*
C14	0.5425 (2)	0.45720 (15)	0.35776 (11)	0.0192 (3)
C15	0.71296 (19)	0.48563 (15)	0.41141 (11)	0.0207 (3)
H15	0.8114	0.5559	0.4108	0.025*
C16	0.73853 (19)	0.41135 (15)	0.46552 (11)	0.0205 (3)
H16	0.8553	0.4310	0.5011	0.025*
O1A	1.47917 (17)	−0.25272 (15)	1.04226 (11)	0.0415 (4)
N1A	1.11717 (17)	−0.11429 (13)	0.83485 (10)	0.0231 (3)
H2A1	1.665 (3)	−0.190 (2)	0.8742 (19)	0.052 (7)*
H2A2	1.730 (3)	−0.247 (2)	0.9574 (19)	0.053 (7)*
N2A	1.64569 (18)	−0.22442 (15)	0.92436 (11)	0.0272 (3)
C2A	1.1357 (2)	−0.11254 (16)	0.93324 (11)	0.0237 (3)
H2A	1.0583	−0.0875	0.9747	0.028*
C3A	1.2613 (2)	−0.14519 (15)	0.97712 (11)	0.0216 (3)
H3A	1.2692	−0.1431	1.0470	0.026*
C4A	1.37647 (19)	−0.18126 (14)	0.91769 (11)	0.0185 (3)
C5A	1.3580 (2)	−0.18397 (15)	0.81524 (11)	0.0214 (3)
H5A	1.4337	−0.2088	0.7721	0.026*
C6A	1.2278 (2)	−0.14995 (16)	0.77731 (11)	0.0236 (3)
H6A	1.2161	−0.1519	0.7074	0.028*
C7A	1.5068 (2)	−0.22172 (16)	0.96667 (12)	0.0228 (3)
O1B	−0.12272 (15)	0.69755 (12)	0.03549 (9)	0.0288 (3)
N1B	0.19402 (17)	0.50814 (13)	0.22105 (10)	0.0241 (3)
H2B1	−0.332 (3)	0.616 (2)	0.1895 (16)	0.035 (5)*
H2B2	−0.377 (3)	0.680 (2)	0.110 (2)	0.059 (7)*
N2B	−0.3086 (2)	0.64438 (17)	0.13790 (13)	0.0329 (3)
C2B	0.2329 (2)	0.57454 (17)	0.15895 (13)	0.0260 (3)
H2B	0.3452	0.5915	0.1414	0.031*
C3B	0.1202 (2)	0.61983 (15)	0.11890 (12)	0.0226 (3)
H3B	0.1549	0.6668	0.0753	0.027*
C4B	−0.04527 (19)	0.59584 (14)	0.14318 (11)	0.0186 (3)
C5B	−0.0896 (2)	0.52331 (16)	0.20509 (11)	0.0230 (3)
H5B	−0.2026	0.5022	0.2218	0.028*
C6B	0.0329 (2)	0.48243 (16)	0.24191 (12)	0.0248 (3)
H6B	0.0010	0.4334	0.2843	0.030*
C7B	−0.1631 (2)	0.64985 (16)	0.10111 (11)	0.0220 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0187 (5)	0.0299 (6)	0.0253 (5)	0.0138 (5)	0.0099 (4)	0.0185 (5)
O4	0.0219 (5)	0.0341 (6)	0.0246 (5)	0.0153 (5)	0.0127 (4)	0.0193 (5)
O5	0.0212 (5)	0.0383 (7)	0.0306 (5)	0.0168 (5)	0.0141 (4)	0.0236 (5)
O7	0.0242 (6)	0.0319 (6)	0.0251 (5)	0.0166 (5)	0.0101 (4)	0.0198 (5)
O14	0.0244 (6)	0.0301 (6)	0.0281 (5)	0.0154 (5)	0.0080 (4)	0.0197 (5)
C2	0.0212 (7)	0.0260 (8)	0.0223 (6)	0.0134 (6)	0.0085 (5)	0.0148 (6)
C3	0.0171 (7)	0.0204 (7)	0.0169 (6)	0.0083 (6)	0.0040 (5)	0.0093 (5)
C4	0.0178 (7)	0.0206 (7)	0.0169 (6)	0.0084 (6)	0.0054 (5)	0.0094 (5)
C5	0.0187 (7)	0.0230 (7)	0.0190 (6)	0.0100 (6)	0.0073 (5)	0.0102 (5)
C6	0.0200 (7)	0.0272 (8)	0.0207 (6)	0.0132 (6)	0.0078 (5)	0.0128 (6)
C7	0.0229 (7)	0.0212 (7)	0.0173 (6)	0.0104 (6)	0.0061 (5)	0.0111 (5)
C8	0.0212 (7)	0.0257 (8)	0.0194 (6)	0.0121 (6)	0.0088 (5)	0.0142 (6)
C9	0.0157 (7)	0.0211 (7)	0.0186 (6)	0.0092 (6)	0.0054 (5)	0.0088 (5)
C10	0.0172 (7)	0.0198 (7)	0.0155 (5)	0.0094 (6)	0.0054 (5)	0.0090 (5)
C11	0.0207 (7)	0.0230 (7)	0.0179 (6)	0.0114 (6)	0.0073 (5)	0.0113 (5)
C12	0.0181 (7)	0.0221 (7)	0.0203 (6)	0.0087 (6)	0.0069 (5)	0.0105 (5)
C13	0.0196 (7)	0.0258 (8)	0.0196 (6)	0.0127 (6)	0.0053 (5)	0.0105 (6)
C14	0.0238 (7)	0.0230 (7)	0.0192 (6)	0.0148 (6)	0.0077 (5)	0.0119 (5)
C15	0.0194 (7)	0.0233 (7)	0.0235 (6)	0.0090 (6)	0.0075 (5)	0.0128 (6)
C16	0.0179 (7)	0.0258 (8)	0.0217 (6)	0.0096 (6)	0.0047 (5)	0.0129 (6)
O1A	0.0376 (7)	0.0793 (10)	0.0489 (8)	0.0393 (7)	0.0270 (6)	0.0527 (8)
N1A	0.0255 (7)	0.0303 (7)	0.0221 (6)	0.0149 (6)	0.0089 (5)	0.0155 (5)
N2A	0.0247 (7)	0.0427 (9)	0.0303 (7)	0.0210 (7)	0.0132 (6)	0.0240 (6)
C2A	0.0283 (8)	0.0321 (9)	0.0228 (6)	0.0197 (7)	0.0127 (6)	0.0152 (6)
C3A	0.0247 (8)	0.0293 (8)	0.0190 (6)	0.0151 (7)	0.0089 (5)	0.0138 (6)
C4A	0.0190 (7)	0.0235 (7)	0.0195 (6)	0.0111 (6)	0.0068 (5)	0.0126 (6)
C5A	0.0241 (7)	0.0271 (8)	0.0204 (6)	0.0135 (6)	0.0099 (5)	0.0133 (6)
C6A	0.0278 (8)	0.0325 (8)	0.0199 (6)	0.0169 (7)	0.0098 (6)	0.0152 (6)
C7A	0.0229 (8)	0.0301 (8)	0.0260 (7)	0.0145 (7)	0.0092 (6)	0.0184 (6)
O1B	0.0279 (6)	0.0432 (7)	0.0313 (6)	0.0202 (6)	0.0126 (5)	0.0257 (5)
N1B	0.0242 (7)	0.0286 (7)	0.0246 (6)	0.0136 (6)	0.0052 (5)	0.0135 (5)
N2B	0.0265 (8)	0.0545 (10)	0.0421 (8)	0.0249 (7)	0.0171 (6)	0.0365 (8)
C2B	0.0219 (8)	0.0352 (9)	0.0303 (8)	0.0149 (7)	0.0095 (6)	0.0194 (7)
C3B	0.0213 (7)	0.0295 (8)	0.0258 (7)	0.0124 (7)	0.0096 (6)	0.0177 (6)
C4B	0.0175 (7)	0.0213 (7)	0.0181 (6)	0.0077 (6)	0.0033 (5)	0.0091 (5)
C5B	0.0190 (7)	0.0305 (8)	0.0240 (7)	0.0095 (6)	0.0069 (6)	0.0160 (6)
C6B	0.0257 (8)	0.0292 (8)	0.0264 (7)	0.0119 (7)	0.0076 (6)	0.0173 (6)
C7B	0.0206 (7)	0.0288 (8)	0.0231 (6)	0.0121 (6)	0.0064 (5)	0.0148 (6)

Geometric parameters (Å, º) top

O1—C2	1.3568 (17)	C16—H16	0.9500
O1—C9	1.3686 (17)	O1A—C7A	1.2311 (18)
O4—C4	1.2580 (16)	N1A—C2A	1.3419 (19)
O5—C5	1.3517 (17)	N1A—C6A	1.3442 (19)
O5—H5	0.97 (2)	N2A—C7A	1.3358 (19)
O7—C7	1.3542 (17)	N2A—H2A1	0.91 (2)
O7—H7	0.95 (3)	N2A—H2A2	0.95 (2)
O14—C14	1.3669 (17)	C2A—C3A	1.377 (2)
O14—H14	0.87 (3)	C2A—H2A	0.9500
C2—C3	1.3527 (19)	C3A—C4A	1.3915 (19)
C2—H2	0.9500	C3A—H3A	0.9500
C3—C4	1.455 (2)	C4A—C5A	1.3933 (19)
C3—C11	1.484 (2)	C4A—C7A	1.506 (2)
C4—C10	1.4411 (19)	C5A—C6A	1.384 (2)
C5—C6	1.375 (2)	C5A—H5A	0.9500
C5—C10	1.421 (2)	C6A—H6A	0.9500
C6—C7	1.4051 (19)	O1B—C7B	1.2330 (18)
C6—H6	0.9500	N1B—C2B	1.337 (2)
C7—C8	1.387 (2)	N1B—C6B	1.339 (2)
C8—C9	1.3821 (19)	N2B—C7B	1.333 (2)
C8—H8	0.9500	N2B—H2B1	0.90 (2)
C9—C10	1.4009 (19)	N2B—H2B2	0.93 (3)
C11—C12	1.397 (2)	C2B—C3B	1.377 (2)
C11—C16	1.400 (2)	C2B—H2B	0.9500
C12—C13	1.389 (2)	C3B—C4B	1.391 (2)
C12—H12	0.9500	C3B—H3B	0.9500
C13—C14	1.387 (2)	C4B—C5B	1.393 (2)
C13—H13	0.9500	C4B—C7B	1.501 (2)
C14—C15	1.396 (2)	C5B—C6B	1.382 (2)
C15—C16	1.384 (2)	C5B—H5B	0.9500
C15—H15	0.9500	C6B—H6B	0.9500

C2—O1—C9	118.88 (11)	C15—C16—H16	119.2
C5—O5—H5	103.1 (14)	C11—C16—H16	119.2
C7—O7—H7	111.7 (16)	C2A—N1A—C6A	117.54 (13)
C14—O14—H14	108.2 (16)	C7A—N2A—H2A1	118.2 (15)
C3—C2—O1	125.34 (13)	C7A—N2A—H2A2	117.7 (14)
C3—C2—H2	117.3	H2A1—N2A—H2A2	123 (2)
O1—C2—H2	117.3	N1A—C2A—C3A	123.29 (13)
C2—C3—C4	118.31 (13)	N1A—C2A—H2A	118.4
C2—C3—C11	119.93 (13)	C3A—C2A—H2A	118.4
C4—C3—C11	121.74 (12)	C2A—C3A—C4A	119.09 (13)
O4—C4—C10	121.24 (13)	C2A—C3A—H3A	120.5
O4—C4—C3	122.77 (13)	C4A—C3A—H3A	120.5
C10—C4—C3	115.99 (11)	C3A—C4A—C5A	118.15 (13)
O5—C5—C6	119.38 (13)	C3A—C4A—C7A	117.49 (12)
O5—C5—C10	119.66 (13)	C5A—C4A—C7A	124.28 (12)
C6—C5—C10	120.94 (12)	C6A—C5A—C4A	118.94 (13)
C5—C6—C7	119.47 (13)	C6A—C5A—H5A	120.5
C5—C6—H6	120.3	C4A—C5A—H5A	120.5
C7—C6—H6	120.3	N1A—C6A—C5A	122.99 (13)
O7—C7—C8	117.55 (12)	N1A—C6A—H6A	118.5
O7—C7—C6	121.02 (13)	C5A—C6A—H6A	118.5
C8—C7—C6	121.43 (13)	O1A—C7A—N2A	123.15 (14)
C9—C8—C7	117.95 (12)	O1A—C7A—C4A	118.79 (13)
C9—C8—H8	121.0	N2A—C7A—C4A	118.05 (13)
C7—C8—H8	121.0	C2B—N1B—C6B	116.63 (13)
O1—C9—C8	116.69 (12)	C7B—N2B—H2B1	122.1 (13)
O1—C9—C10	120.23 (13)	C7B—N2B—H2B2	114.8 (16)
C8—C9—C10	123.08 (13)	H2B1—N2B—H2B2	123 (2)
C9—C10—C5	117.13 (13)	N1B—C2B—C3B	124.04 (14)
C9—C10—C4	121.01 (12)	N1B—C2B—H2B	118.0
C5—C10—C4	121.84 (12)	C3B—C2B—H2B	118.0
C12—C11—C16	117.47 (13)	C2B—C3B—C4B	119.07 (14)
C12—C11—C3	121.52 (13)	C2B—C3B—H3B	120.5
C16—C11—C3	120.93 (13)	C4B—C3B—H3B	120.5
C13—C12—C11	121.45 (14)	C3B—C4B—C5B	117.47 (13)
C13—C12—H12	119.3	C3B—C4B—C7B	117.87 (13)
C11—C12—H12	119.3	C5B—C4B—C7B	124.66 (13)
C14—C13—C12	120.13 (14)	C6B—C5B—C4B	119.17 (14)
C14—C13—H13	119.9	C6B—C5B—H5B	120.4
C12—C13—H13	119.9	C4B—C5B—H5B	120.4
O14—C14—C13	122.36 (13)	N1B—C6B—C5B	123.58 (14)
O14—C14—C15	118.24 (13)	N1B—C6B—H6B	118.2
C13—C14—C15	119.40 (13)	C5B—C6B—H6B	118.2
C16—C15—C14	119.97 (14)	O1B—C7B—N2B	122.72 (14)
C16—C15—H15	120.0	O1B—C7B—C4B	119.77 (13)
C14—C15—H15	120.0	N2B—C7B—C4B	117.50 (13)
C15—C16—C11	121.54 (14)

C9—O1—C2—C3	4.2 (2)	C3—C11—C12—C13	178.40 (12)
O1—C2—C3—C4	0.1 (2)	C11—C12—C13—C14	−0.5 (2)
O1—C2—C3—C11	−178.44 (14)	C12—C13—C14—O14	178.39 (12)
C2—C3—C4—O4	176.76 (14)	C12—C13—C14—C15	−1.3 (2)
C11—C3—C4—O4	−4.8 (2)	O14—C14—C15—C16	−177.81 (12)
C2—C3—C4—C10	−3.6 (2)	C13—C14—C15—C16	1.9 (2)
C11—C3—C4—C10	174.90 (12)	C14—C15—C16—C11	−0.7 (2)
O5—C5—C6—C7	178.47 (13)	C12—C11—C16—C15	−1.1 (2)
C10—C5—C6—C7	−0.3 (2)	C3—C11—C16—C15	−177.81 (13)
C5—C6—C7—O7	178.84 (14)	C6A—N1A—C2A—C3A	0.0 (2)
C5—C6—C7—C8	−0.4 (2)	N1A—C2A—C3A—C4A	0.4 (3)
O7—C7—C8—C9	−178.71 (13)	C2A—C3A—C4A—C5A	−0.6 (2)
C6—C7—C8—C9	0.6 (2)	C2A—C3A—C4A—C7A	−177.47 (14)
C2—O1—C9—C8	175.27 (13)	C3A—C4A—C5A—C6A	0.5 (2)
C2—O1—C9—C10	−4.7 (2)	C7A—C4A—C5A—C6A	177.09 (15)
C7—C8—C9—O1	−179.95 (13)	C2A—N1A—C6A—C5A	−0.2 (2)
C7—C8—C9—C10	0.0 (2)	C4A—C5A—C6A—N1A	−0.1 (3)
O1—C9—C10—C5	179.26 (13)	C3A—C4A—C7A—O1A	18.0 (2)
C8—C9—C10—C5	−0.7 (2)	C5A—C4A—C7A—O1A	−158.63 (16)
O1—C9—C10—C4	1.1 (2)	C3A—C4A—C7A—N2A	−163.23 (15)
C8—C9—C10—C4	−178.87 (14)	C5A—C4A—C7A—N2A	20.2 (2)
O5—C5—C10—C9	−177.93 (13)	C6B—N1B—C2B—C3B	1.9 (2)
C6—C5—C10—C9	0.8 (2)	N1B—C2B—C3B—C4B	−0.2 (3)
O5—C5—C10—C4	0.2 (2)	C2B—C3B—C4B—C5B	−1.7 (2)
C6—C5—C10—C4	179.00 (13)	C2B—C3B—C4B—C7B	178.19 (14)
O4—C4—C10—C9	−177.30 (13)	C3B—C4B—C5B—C6B	2.0 (2)
C3—C4—C10—C9	3.0 (2)	C7B—C4B—C5B—C6B	−177.94 (15)
O4—C4—C10—C5	4.6 (2)	C2B—N1B—C6B—C5B	−1.6 (2)
C3—C4—C10—C5	−175.08 (13)	C4B—C5B—C6B—N1B	−0.3 (2)
C2—C3—C11—C12	−34.8 (2)	C3B—C4B—C7B—O1B	9.8 (2)
C4—C3—C11—C12	146.71 (14)	C5B—C4B—C7B—O1B	−170.23 (15)
C2—C3—C11—C16	141.72 (15)	C3B—C4B—C7B—N2B	−169.73 (15)
C4—C3—C11—C16	−36.7 (2)	C5B—C4B—C7B—N2B	10.2 (2)
C16—C11—C12—C13	1.7 (2)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O4	0.97 (2)	1.65 (3)	2.567 (2)	155 (2)
O7—H7···N1A	0.95 (3)	1.74 (3)	2.671 (2)	166 (2)
O14—H14···N1B	0.87 (3)	1.89 (3)	2.727 (2)	162 (2)
N2A—H2A1···O7ⁱ	0.91 (2)	2.33 (2)	3.162 (2)	152 (2)
N2A—H2A2···O1Bⁱⁱ	0.95 (2)	1.96 (3)	2.905 (2)	172 (2)
N2B—H2B1···O14ⁱⁱⁱ	0.90 (2)	2.33 (2)	3.203 (2)	164 (2)
N2B—H2B2···O1A^iv	0.93 (3)	1.97 (3)	2.894 (2)	176 (2)
C2—H2···O5ⁱⁱⁱ	0.95	2.44	3.283 (2)	149
C6A—H6A···O4^v	0.95	2.46	3.370 (2)	160
C5A—H5A···Cg3^v	0.95	2.69	3.497 (2)	143

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

Geometry of selected π–π interactions (Å, °) top

Cg1 is the centroid of the O1/C2–C4/C10/C9 ring, Cg2 that of the C5–C10 ring, Cg3 that of the C11–C16 and Cg4 that of the N1B/C2B–C6B ring.

CgI	CgJ	Cg···Cg^a	Dihedral angle^b	Interplanar distance^c	Offset^d
Cg1	Cg1^vi	3.686 (3)	0	3.582 (2)	0.868 (3)
Cg1	Cg4^vii	3.554 (2)	5.76 (5)	3.454 (2)	0.836 (3)
Cg2	Cg4^vii	3.925 (2)	5.96 (5)	3.423 (2)	1.921 (3)
Cg3	Cg3^vii	3.577 (2)	0	3.393 (2)	1.132 (3)

(a) The distance between ring centroids. (b) The angle between the planes of rings I and J. (c) The perpendicular distance of CgI from ring J. (d) The perpendicular distance of ring I from ring J. Symmetry codes: (vi) -x + 1, -y, -z + 1; (vii) -x + 1, -y + 1, -z + 1.

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