Supra­molecular architectures in two 1:1 cocrystals of 5-fluoro­uracil with 5-bromo­thio­phene-2-carbox­y­lic acid and thio­phene-2-carb­oxy­lic acid

In solid-state engineering, cocrystallization is a strategy actively pursued for pharmaceuticals. Two 1:1 cocrystals of 5-fluoro­uracil (5FU; systematic name: 5-fluoro-1,3-dihydropyrimidine-2,4-dione), namely 5-fluoro­uracil–5-bromo­thio­phene-2-carb­oxy­lic acid (1/1), C₅H₃BrO₂S·C₄H₃FN₂O₂, (I), and 5-fluoro­uracil–thio­phene-2-carb­oxy­lic acid (1/1), C₄H₃FN₂O₂·C₅H₄O₂S, (II), have been synthesized and characterized by single-crystal X-ray diffraction studies. In both cocrystals, carb­oxy­lic acid mol­ecules are linked through an acid–acid R₂²(8) homosynthon (O—H...O) to form a carb­oxy­lic acid dimer and 5FU mol­ecules are connected through two types of base pairs [homosynthon, R₂²(8) motif] via a pair of N—H...O hydrogen bonds. The crystal structures are further stabilized by C—H...O inter­actions in (II) and C—Br...O inter­actions in (I). In both crystal structures, π–π stacking and C—F...π inter­actions are also observed.

Computing details

For both structures, data collection: APEX3 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a). Program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b) for (I); SHELXL2014 (Sheldrick, 2015b) for (II). For both structures, molecular graphics: PLATON (Spek, 2009), Mercury (Macrae et al., 2008) and POVRay (Cason, 2004); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

5-Fluoro-1,3-dihydropyrimidine-2,4-dione–5-bromothiophene-2-carboxylic acid (1/1) (I)

Crystal data

C5H3BrO2S·C4H3FN2O2	Z = 2
Mr = 337.13	F(000) = 332
Triclinic, P1	Dx = 1.977 Mg m^−3
a = 6.8884 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.5036 (6) Å	Cell parameters from 15925 reflections
c = 9.6180 (6) Å	θ = 2.2–26.4°
α = 73.608 (2)°	µ = 3.83 mm^−1
β = 87.634 (2)°	T = 100 K
γ = 69.969 (2)°	Column, colourless
V = 566.43 (6) Å^3	0.33 × 0.08 × 0.07 mm

Data collection

Bruker D8 Venture Photon 100 diffractometer	2194 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.032
φ and ω scans	θmax = 26.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −8→8
Tmin = 0.745, Tmax = 1.000	k = −11→11
15925 measured reflections	l = −12→12
2317 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.019	Hydrogen site location: mixed
wR(F^2) = 0.051	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0276P)^2 + 0.2836P] where P = (Fo^2 + 2Fc^2)/3
2317 reflections	(Δ/σ)max = 0.001
175 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.40 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.58555 (3)	0.24988 (2)	0.24091 (2)	0.02083 (7)
S1	1.02198 (6)	−0.01224 (5)	0.31979 (5)	0.01651 (10)
F1	0.03159 (16)	0.39395 (11)	0.20314 (12)	0.0250 (2)
O1	−0.26161 (18)	1.01827 (13)	−0.00967 (14)	0.0174 (3)
O2	0.29276 (19)	0.56879 (14)	0.13895 (15)	0.0234 (3)
O3	1.25662 (19)	−0.46319 (14)	0.51842 (15)	0.0230 (3)
O4	1.4071 (2)	−0.29176 (15)	0.39859 (15)	0.0218 (3)
N1	−0.3213 (2)	0.78787 (17)	0.06855 (17)	0.0168 (3)
N3	0.0123 (2)	0.79068 (16)	0.06118 (16)	0.0152 (3)
C2	−0.1954 (2)	0.87409 (19)	0.03752 (18)	0.0141 (3)
C4	0.1048 (3)	0.62998 (19)	0.11854 (19)	0.0167 (3)
C5	−0.0446 (3)	0.55091 (19)	0.14866 (19)	0.0168 (3)
C6	−0.2481 (3)	0.6279 (2)	0.12366 (19)	0.0180 (3)
H6	−0.342000	0.572171	0.143905	0.022*
C7	1.0465 (3)	−0.20354 (19)	0.40967 (19)	0.0171 (3)
C8	0.8580 (3)	−0.2205 (2)	0.4387 (2)	0.0203 (4)
H8	0.841631	−0.317163	0.487976	0.024*
C9	0.6907 (3)	−0.0786 (2)	0.3874 (2)	0.0211 (4)
H9	0.549202	−0.068797	0.397146	0.025*
C10	0.7577 (3)	0.0427 (2)	0.32214 (19)	0.0177 (3)
C11	1.2454 (3)	−0.3306 (2)	0.44742 (19)	0.0175 (3)
H1	−0.437 (4)	0.834 (3)	0.054 (2)	0.022 (6)*
H3	0.093 (4)	0.846 (3)	0.043 (2)	0.024 (5)*
H4	1.514 (5)	−0.372 (3)	0.425 (3)	0.047 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02001 (11)	0.01190 (10)	0.02576 (12)	−0.00155 (7)	−0.00404 (7)	−0.00217 (7)
S1	0.0160 (2)	0.0121 (2)	0.0199 (2)	−0.00474 (16)	0.00073 (16)	−0.00224 (16)
F1	0.0217 (5)	0.0102 (5)	0.0363 (6)	−0.0034 (4)	−0.0012 (5)	0.0014 (4)
O1	0.0124 (6)	0.0118 (6)	0.0255 (7)	−0.0031 (4)	0.0007 (5)	−0.0028 (5)
O2	0.0129 (6)	0.0156 (6)	0.0357 (8)	−0.0011 (5)	−0.0031 (5)	−0.0021 (5)
O3	0.0173 (6)	0.0125 (6)	0.0346 (8)	−0.0039 (5)	0.0007 (5)	−0.0012 (5)
O4	0.0162 (6)	0.0139 (6)	0.0308 (7)	−0.0042 (5)	0.0003 (5)	−0.0009 (5)
N1	0.0080 (7)	0.0128 (7)	0.0272 (8)	−0.0023 (6)	−0.0005 (6)	−0.0034 (6)
N3	0.0111 (7)	0.0111 (7)	0.0220 (8)	−0.0039 (5)	0.0002 (6)	−0.0026 (6)
C2	0.0127 (8)	0.0134 (8)	0.0151 (8)	−0.0033 (6)	0.0012 (6)	−0.0042 (6)
C4	0.0154 (8)	0.0128 (8)	0.0188 (9)	−0.0020 (6)	−0.0010 (7)	−0.0031 (6)
C5	0.0193 (8)	0.0088 (7)	0.0193 (9)	−0.0039 (6)	−0.0007 (7)	−0.0006 (6)
C6	0.0182 (8)	0.0140 (8)	0.0227 (9)	−0.0077 (7)	0.0018 (7)	−0.0037 (7)
C7	0.0193 (9)	0.0123 (8)	0.0190 (9)	−0.0052 (6)	−0.0004 (7)	−0.0034 (6)
C8	0.0204 (9)	0.0143 (8)	0.0252 (10)	−0.0072 (7)	0.0002 (7)	−0.0025 (7)
C9	0.0160 (9)	0.0177 (9)	0.0292 (10)	−0.0064 (7)	0.0001 (7)	−0.0053 (7)
C10	0.0159 (8)	0.0148 (8)	0.0202 (9)	−0.0024 (6)	−0.0019 (7)	−0.0047 (7)
C11	0.0183 (8)	0.0146 (8)	0.0196 (9)	−0.0054 (7)	−0.0008 (7)	−0.0049 (7)

Geometric parameters (Å, º)

Br1—C10	1.8712 (17)	N3—C2	1.369 (2)
S1—C10	1.7143 (18)	N3—C4	1.389 (2)
S1—C7	1.7308 (17)	N3—H3	0.86 (2)
F1—C5	1.3492 (19)	C4—C5	1.446 (2)
O1—C2	1.237 (2)	C5—C6	1.335 (2)
O2—C4	1.222 (2)	C6—H6	0.9500
O3—C11	1.229 (2)	C7—C8	1.370 (3)
O4—C11	1.319 (2)	C7—C11	1.458 (2)
O4—H4	0.84 (3)	C8—C9	1.413 (2)
N1—C2	1.356 (2)	C8—H8	0.9500
N1—C6	1.375 (2)	C9—C10	1.367 (2)
N1—H1	0.77 (2)	C9—H9	0.9500
C10—S1—C7	90.45 (8)	C5—C6—H6	120.1
C11—O4—H4	108.2 (19)	N1—C6—H6	120.1
C2—N1—C6	122.94 (15)	C8—C7—C11	124.66 (16)
C2—N1—H1	116.0 (17)	C8—C7—S1	111.96 (13)
C6—N1—H1	121.1 (17)	C11—C7—S1	123.38 (13)
C2—N3—C4	126.93 (14)	C7—C8—C9	112.72 (16)
C2—N3—H3	115.6 (15)	C7—C8—H8	123.6
C4—N3—H3	117.4 (15)	C9—C8—H8	123.6
O1—C2—N1	122.87 (15)	C10—C9—C8	111.60 (16)
O1—C2—N3	121.65 (15)	C10—C9—H9	124.2
N1—C2—N3	115.48 (14)	C8—C9—H9	124.2
O2—C4—N3	121.07 (16)	C9—C10—S1	113.27 (13)
O2—C4—C5	126.42 (15)	C9—C10—Br1	125.04 (14)
N3—C4—C5	112.51 (14)	S1—C10—Br1	121.68 (10)
C6—C5—F1	121.13 (15)	O3—C11—O4	123.82 (16)
C6—C5—C4	122.25 (15)	O3—C11—C7	121.27 (16)
F1—C5—C4	116.62 (15)	O4—C11—C7	114.91 (15)
C5—C6—N1	119.82 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.76 (3)	2.05 (3)	2.809 (2)	173 (3)
N3—H3···O1^ii	0.87 (3)	1.97 (3)	2.837 (2)	176 (2)
O4—H4···O3^iii	0.84 (3)	1.77 (3)	2.614 (2)	178 (4)
C6—H6···O2^iv	0.95	2.53	3.387 (3)	150
C8—H8···O3^v	0.95	2.42	3.276 (2)	150

Symmetry codes: (i) −x−1, −y+2, −z; (ii) −x, −y+2, −z; (iii) −x+3, −y−1, −z+1; (iv) x−1, y, z; (v) −x+2, −y−1, −z+1.

5-Fluoro-1,3-dihydropyrimidine-2,4-dione–thiophene-2-carboxylic acid (1/1) (II)

Crystal data

C4H3FN2O2·C5H4O2S	Z = 2
Mr = 258.23	F(000) = 264
Triclinic, P1	Dx = 1.684 Mg m^−3
a = 6.8304 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.0075 (4) Å	Cell parameters from 9804 reflections
c = 12.3042 (6) Å	θ = 3.3–28.3°
α = 93.348 (2)°	µ = 0.34 mm^−1
β = 103.091 (1)°	T = 100 K
γ = 115.566 (1)°	Column, colourless
V = 509.22 (4) Å^3	0.38 × 0.11 × 0.11 mm

Data collection

Bruker D8 Venture Photon 100 diffractometer	2357 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.023
φ and ω scans	θmax = 28.3°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −7→9
Tmin = 0.913, Tmax = 1.000	k = −9→9
11445 measured reflections	l = −16→16
2525 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.028	Hydrogen site location: mixed
wR(F^2) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0386P)^2 + 0.1738P] where P = (Fo^2 + 2Fc^2)/3
2525 reflections	(Δ/σ)max = 0.001
187 parameters	Δρmax = 0.37 e Å^−3
10 restraints	Δρmin = −0.32 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
F5	0.00118 (11)	0.30564 (11)	0.05970 (5)	0.02370 (16)
O1	0.25578 (13)	0.51105 (13)	0.51342 (6)	0.02083 (18)
O2	0.40406 (13)	0.32871 (13)	0.19059 (6)	0.02030 (17)
N1	−0.00787 (14)	0.43648 (14)	0.34484 (7)	0.01586 (18)
H1	−0.094 (2)	0.457 (2)	0.3786 (12)	0.022 (3)*
N3	0.32358 (14)	0.41751 (14)	0.35057 (7)	0.01623 (19)
H3	0.454 (2)	0.431 (2)	0.3924 (13)	0.032 (4)*
C2	0.19242 (17)	0.45695 (16)	0.40839 (9)	0.0154 (2)
C4	0.27477 (17)	0.36230 (16)	0.23342 (8)	0.0154 (2)
C5	0.06057 (17)	0.35276 (16)	0.17355 (8)	0.0164 (2)
C6	−0.07365 (17)	0.38684 (16)	0.22804 (9)	0.0164 (2)
H6	−0.2140	0.3768	0.1863	0.020*
S1A	0.50067 (8)	0.85187 (10)	0.13743 (3)	0.01907 (13)	0.8318 (16)
C7A	0.6604 (10)	0.8915 (19)	0.2741 (3)	0.0168 (4)	0.8318 (16)
C8A	0.8511 (13)	0.8729 (14)	0.2758 (6)	0.0196 (9)	0.8318 (16)
H8A	0.9589	0.8879	0.3442	0.024*	0.8318 (16)
C9A	0.8754 (3)	0.8300 (4)	0.16898 (15)	0.0205 (3)	0.8318 (16)
H9A	1.0008	0.8157	0.1562	0.025*	0.8318 (16)
C10A	0.6940 (3)	0.8109 (3)	0.08448 (15)	0.0202 (3)	0.8318 (16)
H10A	0.6777	0.7789	0.0059	0.024*	0.8318 (16)
C11A	0.5891 (12)	0.938 (2)	0.3713 (3)	0.0171 (4)	0.8318 (16)
O3A	0.7151 (12)	0.9703 (16)	0.4707 (5)	0.0262 (7)	0.8318 (16)
O4A	0.3972 (6)	0.9389 (7)	0.35536 (17)	0.0221 (4)	0.8318 (16)
H4A	0.3785	0.9682	0.4183	0.033*	0.8318 (16)
S1B	0.8842 (18)	0.8707 (18)	0.2879 (8)	0.0196 (9)	0.1682 (16)
C7B	0.636 (5)	0.887 (10)	0.2725 (13)	0.0168 (4)	0.1682 (16)
C8B	0.528 (2)	0.860 (3)	0.1612 (9)	0.01907 (13)	0.1682 (16)
H8B	0.3908	0.8693	0.1369	0.023*	0.1682 (16)
C9B	0.828 (2)	0.814 (2)	0.1436 (8)	0.0205 (3)	0.1682 (16)
H9B	0.9223	0.7825	0.1074	0.025*	0.1682 (16)
C10B	0.6340 (16)	0.8170 (19)	0.0855 (10)	0.0202 (3)	0.1682 (16)
H10B	0.5794	0.7936	0.0053	0.024*	0.1682 (16)
C11B	0.571 (6)	0.933 (13)	0.3718 (17)	0.0171 (4)	0.1682 (16)
O3B	0.725 (7)	0.985 (8)	0.464 (3)	0.0262 (7)	0.1682 (16)
H3B	0.6738	0.9950	0.5189	0.039*	0.1682 (16)
O4B	0.377 (3)	0.928 (4)	0.3352 (12)	0.0221 (4)	0.1682 (16)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F5	0.0248 (3)	0.0363 (4)	0.0111 (3)	0.0157 (3)	0.0040 (2)	0.0026 (3)
O1	0.0161 (4)	0.0348 (4)	0.0135 (4)	0.0141 (3)	0.0039 (3)	−0.0011 (3)
O2	0.0198 (4)	0.0287 (4)	0.0175 (4)	0.0140 (3)	0.0089 (3)	0.0026 (3)
N1	0.0128 (4)	0.0221 (4)	0.0150 (4)	0.0099 (3)	0.0049 (3)	0.0009 (3)
N3	0.0133 (4)	0.0244 (4)	0.0130 (4)	0.0108 (3)	0.0035 (3)	0.0009 (3)
C2	0.0138 (4)	0.0184 (4)	0.0150 (4)	0.0078 (4)	0.0051 (4)	0.0012 (3)
C4	0.0158 (5)	0.0172 (4)	0.0143 (4)	0.0075 (4)	0.0065 (4)	0.0022 (3)
C5	0.0172 (5)	0.0201 (5)	0.0115 (4)	0.0083 (4)	0.0034 (4)	0.0021 (3)
C6	0.0141 (4)	0.0185 (4)	0.0160 (5)	0.0078 (4)	0.0025 (4)	0.0026 (4)
S1A	0.0183 (2)	0.02611 (18)	0.0110 (2)	0.00991 (16)	0.00191 (17)	0.00117 (19)
C7A	0.0170 (15)	0.0184 (7)	0.0142 (5)	0.0069 (16)	0.0055 (6)	0.0023 (4)
C8A	0.020 (2)	0.0250 (4)	0.0161 (14)	0.0129 (11)	0.0043 (13)	0.0047 (8)
C9A	0.0205 (10)	0.0225 (7)	0.0214 (9)	0.0114 (8)	0.0084 (7)	0.0029 (8)
C10A	0.0244 (10)	0.0244 (5)	0.0158 (5)	0.0122 (7)	0.0112 (7)	0.0018 (4)
C11A	0.0171 (14)	0.0190 (9)	0.0157 (5)	0.0080 (16)	0.0060 (5)	0.0027 (4)
O3A	0.0256 (8)	0.0422 (17)	0.0138 (10)	0.0190 (9)	0.0044 (8)	0.0020 (7)
O4A	0.0192 (8)	0.0371 (7)	0.0114 (10)	0.0150 (7)	0.0035 (8)	0.0000 (10)
S1B	0.020 (2)	0.0250 (4)	0.0161 (14)	0.0129 (11)	0.0043 (13)	0.0047 (8)
C7B	0.0170 (15)	0.0184 (7)	0.0142 (5)	0.0069 (16)	0.0055 (6)	0.0023 (4)
C8B	0.0183 (2)	0.02611 (18)	0.0110 (2)	0.00991 (16)	0.00191 (17)	0.00117 (19)
C9B	0.0205 (10)	0.0225 (7)	0.0214 (9)	0.0114 (8)	0.0084 (7)	0.0029 (8)
C10B	0.0244 (10)	0.0244 (5)	0.0158 (5)	0.0122 (7)	0.0112 (7)	0.0018 (4)
C11B	0.0171 (14)	0.0190 (9)	0.0157 (5)	0.0080 (16)	0.0060 (5)	0.0027 (4)
O3B	0.0256 (8)	0.0422 (17)	0.0138 (10)	0.0190 (9)	0.0044 (8)	0.0020 (7)
O4B	0.0192 (8)	0.0371 (7)	0.0114 (10)	0.0150 (7)	0.0035 (8)	0.0000 (10)

Geometric parameters (Å, º)

F5—C5	1.3449 (11)	C9A—C10A	1.375 (2)
O1—C2	1.2445 (12)	C9A—H9A	0.9500
O2—C4	1.2202 (13)	C10A—H10A	0.9500
N1—C2	1.3553 (13)	C11A—O3A	1.269 (3)
N1—C6	1.3793 (13)	C11A—O4A	1.2849 (17)
N1—H1	0.846 (13)	O4A—H4A	0.8400
N3—C2	1.3655 (13)	S1B—C9B	1.714 (5)
N3—C4	1.3944 (12)	S1B—C7B	1.714 (6)
N3—H3	0.883 (13)	C7B—C8B	1.360 (8)
C4—C5	1.4524 (14)	C7B—C11B	1.458 (5)
C5—C6	1.3400 (14)	C8B—C10B	1.393 (8)
C6—H6	0.9500	C8B—H8B	0.9500
S1A—C10A	1.7164 (15)	C9B—C10B	1.365 (5)
S1A—C7A	1.717 (3)	C9B—H9B	0.9500
C7A—C8A	1.360 (6)	C10B—H10B	0.9500
C7A—C11A	1.4581 (17)	C11B—O3B	1.270 (5)
C8A—C9A	1.393 (7)	C11B—O4B	1.285 (5)
C8A—H8A	0.9500	O3B—H3B	0.8400
C2—N1—C6	122.43 (9)	C10A—C9A—H9A	124.4
C2—N1—H1	118.2 (10)	C8A—C9A—H9A	124.4
C6—N1—H1	119.3 (10)	C9A—C10A—S1A	112.20 (15)
C2—N3—C4	126.89 (9)	C9A—C10A—H10A	123.9
C2—N3—H3	115.8 (11)	S1A—C10A—H10A	123.9
C4—N3—H3	117.3 (11)	O3A—C11A—O4A	120.9 (6)
O1—C2—N1	122.30 (9)	O3A—C11A—C7A	119.4 (6)
O1—C2—N3	121.47 (9)	O4A—C11A—C7A	119.7 (3)
N1—C2—N3	116.22 (9)	C11A—O4A—H4A	109.5
O2—C4—N3	121.41 (9)	C9B—S1B—C7B	90.4 (9)
O2—C4—C5	126.36 (10)	C8B—C7B—C11B	128.4 (15)
N3—C4—C5	112.23 (9)	C8B—C7B—S1B	111.1 (12)
C6—C5—F5	121.13 (9)	C11B—C7B—S1B	120.5 (12)
C6—C5—C4	122.23 (9)	C7B—C8B—C10B	114.8 (13)
F5—C5—C4	116.64 (9)	C7B—C8B—H8B	122.6
C5—C6—N1	119.94 (9)	C10B—C8B—H8B	122.6
C5—C6—H6	120.0	C10B—C9B—S1B	113.6 (10)
N1—C6—H6	120.0	C10B—C9B—H9B	123.2
C10A—S1A—C7A	91.18 (12)	S1B—C9B—H9B	123.2
C8A—C7A—C11A	127.3 (4)	C9B—C10B—C8B	110.0 (11)
C8A—C7A—S1A	111.0 (4)	C9B—C10B—H10B	125.0
C11A—C7A—S1A	121.7 (2)	C8B—C10B—H10B	125.0
C7A—C8A—C9A	114.4 (5)	O3B—C11B—O4B	139 (3)
C7A—C8A—H8A	122.8	O3B—C11B—C7B	113 (3)
C9A—C8A—H8A	122.8	O4B—C11B—C7B	106.9 (17)
C10A—C9A—C8A	111.2 (4)	C11B—O3B—H3B	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.85 (2)	1.97 (2)	2.8008 (13)	167 (1)
N3—H3···O1^ii	0.88 (2)	1.91 (2)	2.7908 (13)	175 (1)
O4A—H4A···O3A^iii	0.84	1.74	2.565 (8)	167
C6—H6···O2^iv	0.95	2.50	3.3293 (16)	147
C8A—H8A···O3A^v	0.95	2.58	3.510 (11)	166
C10A—H10A···O2^vi	0.95	2.35	3.2987 (19)	174

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