4-{[7-(Trifluoro-meth-yl)quinolin-4-yl]amino}-benzene-sulfonamide-ethanol-methanol (1/0.47/0.53).

In the title compound, C(16)H(12)F(3)N(3)O(2)S·0.47C(2)H(5)OH·0.53CH(3)OH, the quinoline ring system is approximately planar, with a maximum deviation of 0.035 (3) Å, and makes a dihedral angle of 52.67 (9)° with the benzene ring. The F atoms of the -CF(3) group are disordered over two orientations, with refined site occupancies of 0.56 (2) and 0.44 (2). A single solvate site is occupied at random by ethanol or methanol, with refined site occupancies of 0.470 (6) and 0.530 (6), respectively. In the crystal, mol-ecules are linked via N-H⋯O, N-H⋯N, O-H⋯O and C-H⋯O hydrogen bonds, thereby forming sheets lying parallel to (010).

Related literature

For background to the biological and pharmacological activity of quinolines, see: Ghorab et al. (2011 ▶, 2012 ▶).

Experimental

Crystal data

C16H12F3N3O2S·0.47C2H6O·0.53CH4O

M = 405.98

Triclinic,

a = 8.6037 (1) Å

b = 9.3146 (2) Å

c = 11.4590 (2) Å

α = 92.463 (1)°

β = 91.544 (1)°

γ = 92.969 (1)°

V = 915.85 (3) Å3

Z = 2

Cu Kα radiation

μ = 2.07 mm−1

T = 296 K

0.83 × 0.43 × 0.11 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.279, T max = 0.801

9433 measured reflections

2845 independent reflections

2631 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.129

S = 1.05

2845 reflections

309 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.41 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812029698/hb6882sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029698/hb6882Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029698/hb6882Isup3.cml

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

C16H12F3N3O2S·0.47C2H6O·0.53CH4O	Z = 2
Mr = 405.98	F(000) = 420
Triclinic, P1	Dx = 1.472 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 8.6037 (1) Å	Cell parameters from 2059 reflections
b = 9.3146 (2) Å	θ = 3.9–70.4°
c = 11.4590 (2) Å	µ = 2.07 mm−1
α = 92.463 (1)°	T = 296 K
β = 91.544 (1)°	Plate, colorless
γ = 92.969 (1)°	0.83 × 0.43 × 0.11 mm
V = 915.85 (3) Å3

Bruker SMART APEXII CCD diffractometer	2845 independent reflections
Radiation source: fine-focus sealed tube	2631 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 63.0°, θmin = 3.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.279, Tmax = 0.801	k = −10→10
9433 measured reflections	l = −12→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.129	w = 1/[σ2(Fo2) + (0.0745P)2 + 0.2909P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2845 reflections	Δρmax = 0.34 e Å−3
309 parameters	Δρmin = −0.41 e Å−3
2 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0031 (7)

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	Occ. (<1)
S1	0.13678 (6)	1.19048 (6)	0.59873 (4)	0.0525 (2)
F1A	1.3524 (19)	0.588 (2)	1.0571 (10)	0.172 (6)	0.56 (2)
F2A	1.2936 (12)	0.4416 (8)	0.9214 (12)	0.116 (4)	0.56 (2)
F3A	1.4169 (11)	0.630 (2)	0.887 (2)	0.165 (5)	0.56 (2)
F1B	1.321 (2)	0.470 (2)	0.8836 (18)	0.154 (7)	0.44 (2)
F2B	1.2955 (16)	0.5212 (19)	1.0590 (12)	0.137 (5)	0.44 (2)
F3B	1.4139 (11)	0.6569 (10)	0.961 (2)	0.118 (4)	0.44 (2)
N1	0.8884 (2)	0.8734 (2)	1.08416 (15)	0.0558 (5)
N2	0.6928 (3)	0.8826 (3)	0.74398 (17)	0.0723 (6)
H1N2	0.7094	0.8068	0.6996	0.094*
N3	−0.0014 (2)	1.1225 (3)	0.67275 (19)	0.0607 (5)
O1	0.0977 (2)	1.15432 (19)	0.47846 (13)	0.0640 (4)
O2	0.1626 (2)	1.33775 (18)	0.63484 (16)	0.0724 (5)
C1	0.7685 (3)	0.9498 (3)	1.05917 (19)	0.0577 (6)
H1A	0.7267	1.0026	1.1203	0.069*
C2	0.6992 (2)	0.9581 (3)	0.94910 (19)	0.0545 (5)
H2A	0.6143	1.0145	0.9388	0.065*
C3	0.7565 (2)	0.8827 (2)	0.85519 (18)	0.0512 (5)
C4	0.8899 (2)	0.8004 (2)	0.87623 (18)	0.0499 (5)
C5	0.9674 (3)	0.7244 (3)	0.7879 (2)	0.0648 (6)
H5A	0.9300	0.7250	0.7110	0.078*
C6	1.0946 (3)	0.6508 (3)	0.8123 (2)	0.0680 (7)
H6A	1.1438	0.6016	0.7527	0.082*
C7	1.1524 (3)	0.6487 (3)	0.9279 (2)	0.0606 (6)
C8	1.0800 (3)	0.7194 (2)	1.0154 (2)	0.0564 (5)
H8A	1.1178	0.7155	1.0919	0.068*
C9	0.9493 (2)	0.7981 (2)	0.99220 (18)	0.0489 (5)
C10	1.3000 (3)	0.5751 (3)	0.9526 (3)	0.0769 (8)
C11	0.5640 (3)	0.9600 (3)	0.70824 (19)	0.0596 (6)
C12	0.5560 (3)	1.1052 (3)	0.7346 (2)	0.0616 (6)
H12A	0.6380	1.1554	0.7756	0.074*
C13	0.4265 (3)	1.1765 (3)	0.7003 (2)	0.0578 (6)
H13A	0.4199	1.2738	0.7203	0.069*
C14	0.3073 (2)	1.1028 (2)	0.63654 (18)	0.0504 (5)
C15	0.3168 (3)	0.9587 (3)	0.6061 (2)	0.0671 (7)
H15A	0.2377	0.9102	0.5609	0.081*
C16	0.4443 (3)	0.8871 (3)	0.6433 (2)	0.0718 (7)
H16A	0.4499	0.7893	0.6246	0.086*
H2N3	0.020 (3)	1.130 (3)	0.746 (3)	0.061 (7)*
H1N3	−0.034 (3)	1.037 (3)	0.645 (3)	0.075 (9)*
O3	0.6404 (7)	0.5947 (6)	0.6144 (5)	0.120 (2)	0.530 (6)
H1O3	0.7187	0.6422	0.5695	0.181*	0.530 (6)
C17	0.7032 (11)	0.4787 (8)	0.6295 (13)	0.148 (4)	0.530 (6)
H17A	0.7984	0.4949	0.6749	0.223*	0.530 (6)
H17B	0.6311	0.4193	0.6712	0.223*	0.530 (6)
H17C	0.7243	0.4313	0.5560	0.223*	0.530 (6)
C18	0.3657 (7)	0.5101 (10)	0.4490 (6)	0.084 (2)	0.470 (6)
H18A	0.4198	0.5162	0.3770	0.100*	0.470 (6)
H18B	0.3355	0.4103	0.4562	0.100*	0.470 (6)
C19	0.2268 (12)	0.5869 (11)	0.4363 (12)	0.131 (4)	0.470 (6)
H19A	0.1698	0.5435	0.3695	0.196*	0.470 (6)
H19B	0.1649	0.5786	0.5043	0.196*	0.470 (6)
H19C	0.2508	0.6867	0.4235	0.196*	0.470 (6)
O4	0.4659 (8)	0.5410 (5)	0.5282 (6)	0.130 (3)	0.470 (6)
H1O4	0.5659	0.5073	0.5128	0.195*	0.470 (6)

	U11	U22	U33	U12	U13	U23
S1	0.0516 (3)	0.0669 (4)	0.0399 (3)	0.0193 (2)	−0.0105 (2)	0.0026 (2)
F1A	0.138 (8)	0.260 (12)	0.120 (7)	0.136 (8)	−0.081 (6)	−0.078 (7)
F2A	0.087 (3)	0.065 (3)	0.196 (12)	0.027 (3)	−0.023 (4)	0.014 (5)
F3A	0.059 (3)	0.210 (10)	0.243 (12)	0.052 (4)	0.031 (5)	0.124 (9)
F1B	0.152 (11)	0.182 (13)	0.128 (8)	0.127 (10)	−0.068 (7)	−0.080 (8)
F2B	0.103 (6)	0.187 (9)	0.132 (9)	0.069 (6)	−0.014 (5)	0.083 (9)
F3B	0.044 (3)	0.105 (4)	0.205 (12)	0.005 (3)	−0.022 (6)	0.029 (6)
N1	0.0571 (11)	0.0718 (11)	0.0393 (10)	0.0096 (9)	−0.0032 (8)	0.0045 (8)
N2	0.0639 (12)	0.1111 (17)	0.0443 (11)	0.0455 (12)	−0.0132 (9)	−0.0094 (10)
N3	0.0517 (11)	0.0880 (16)	0.0435 (12)	0.0193 (10)	−0.0071 (8)	0.0019 (10)
O1	0.0681 (10)	0.0856 (11)	0.0397 (9)	0.0222 (8)	−0.0117 (7)	0.0052 (7)
O2	0.0794 (12)	0.0654 (10)	0.0728 (11)	0.0213 (8)	−0.0194 (9)	−0.0012 (8)
C1	0.0546 (13)	0.0764 (14)	0.0431 (12)	0.0127 (10)	0.0047 (9)	0.0018 (10)
C2	0.0429 (11)	0.0743 (14)	0.0478 (12)	0.0140 (9)	0.0029 (8)	0.0068 (10)
C3	0.0403 (10)	0.0718 (13)	0.0424 (11)	0.0126 (9)	−0.0032 (8)	0.0047 (9)
C4	0.0434 (11)	0.0641 (12)	0.0428 (11)	0.0090 (9)	−0.0035 (8)	0.0037 (9)
C5	0.0629 (14)	0.0883 (17)	0.0447 (13)	0.0271 (12)	−0.0072 (10)	−0.0008 (11)
C6	0.0639 (15)	0.0850 (16)	0.0571 (14)	0.0314 (12)	−0.0046 (11)	−0.0039 (11)
C7	0.0502 (12)	0.0637 (13)	0.0683 (15)	0.0145 (10)	−0.0126 (10)	0.0030 (11)
C8	0.0536 (12)	0.0642 (13)	0.0510 (13)	0.0072 (10)	−0.0156 (10)	0.0052 (10)
C9	0.0448 (11)	0.0595 (11)	0.0423 (11)	0.0032 (9)	−0.0060 (8)	0.0065 (8)
C10	0.0619 (17)	0.0797 (18)	0.090 (2)	0.0252 (14)	−0.0209 (14)	0.0023 (15)
C11	0.0482 (12)	0.0918 (17)	0.0405 (12)	0.0249 (11)	−0.0059 (9)	0.0021 (10)
C12	0.0479 (12)	0.0813 (16)	0.0554 (14)	0.0065 (10)	−0.0125 (10)	0.0054 (11)
C13	0.0528 (12)	0.0680 (13)	0.0529 (13)	0.0087 (10)	−0.0089 (9)	0.0061 (10)
C14	0.0463 (11)	0.0670 (13)	0.0391 (11)	0.0158 (9)	−0.0059 (8)	0.0046 (9)
C15	0.0599 (14)	0.0769 (16)	0.0637 (15)	0.0210 (11)	−0.0241 (11)	−0.0112 (12)
C16	0.0725 (16)	0.0784 (16)	0.0649 (16)	0.0330 (13)	−0.0241 (12)	−0.0127 (12)
O3	0.144 (5)	0.093 (3)	0.119 (4)	0.004 (3)	−0.041 (3)	−0.016 (3)
C17	0.111 (8)	0.139 (10)	0.191 (13)	−0.020 (7)	−0.039 (8)	0.017 (8)
C18	0.068 (4)	0.124 (7)	0.065 (4)	0.050 (4)	0.002 (3)	0.026 (4)
C19	0.104 (7)	0.090 (6)	0.203 (12)	0.024 (5)	0.006 (7)	0.034 (6)
O4	0.160 (6)	0.071 (3)	0.159 (7)	0.004 (3)	0.039 (5)	−0.022 (3)

S1—O2	1.4202 (18)	C7—C10	1.500 (3)
S1—O1	1.4314 (16)	C8—C9	1.399 (3)
S1—N3	1.599 (2)	C8—H8A	0.9300
S1—C14	1.768 (2)	C11—C12	1.379 (4)
F1A—C10	1.266 (8)	C11—C16	1.385 (4)
F2A—C10	1.277 (8)	C12—C13	1.383 (3)
F3A—C10	1.362 (9)	C12—H12A	0.9300
F1B—C10	1.258 (10)	C13—C14	1.379 (3)
F2B—C10	1.339 (10)	C13—H13A	0.9300
F3B—C10	1.209 (9)	C14—C15	1.379 (3)
N1—C1	1.316 (3)	C15—C16	1.381 (3)
N1—C9	1.371 (3)	C15—H15A	0.9300
N2—C3	1.373 (3)	C16—H16A	0.9300
N2—C11	1.414 (3)	O3—C17	1.2497 (11)
N2—H1N2	0.8727	O3—H1O3	0.9600
N3—H2N3	0.86 (3)	C17—H17A	0.9600
N3—H1N3	0.88 (3)	C17—H17B	0.9600
C1—C2	1.387 (3)	C17—H17C	0.9600
C1—H1A	0.9300	C18—O4	1.2485 (11)
C2—C3	1.376 (3)	C18—C19	1.432 (11)
C2—H2A	0.9300	C18—O4i	1.567 (11)
C3—C4	1.434 (3)	C18—H18A	0.9600
C4—C5	1.412 (3)	C18—H18B	0.9600
C4—C9	1.412 (3)	C19—H19A	0.9600
C5—C6	1.350 (3)	C19—H19B	0.9600
C5—H5A	0.9300	C19—H19C	0.9600
C6—C7	1.404 (3)	O4—O4i	1.171 (11)
C6—H6A	0.9300	O4—C18i	1.567 (11)
C7—C8	1.359 (4)	O4—H1O4	0.9500
O2—S1—O1	118.81 (11)	F3B—C10—C7	113.3 (5)
O2—S1—N3	108.50 (13)	F1B—C10—C7	114.0 (6)
O1—S1—N3	106.49 (12)	F1A—C10—C7	115.9 (4)
O2—S1—C14	107.14 (11)	F2A—C10—C7	114.0 (5)
O1—S1—C14	108.12 (10)	F2B—C10—C7	109.6 (5)
N3—S1—C14	107.28 (10)	F3A—C10—C7	110.3 (4)
C1—N1—C9	116.18 (18)	C12—C11—C16	119.6 (2)
C3—N2—C11	126.10 (19)	C12—C11—N2	121.9 (2)
C3—N2—H1N2	115.2	C16—C11—N2	118.5 (2)
C11—N2—H1N2	114.7	C11—C12—C13	120.2 (2)
S1—N3—H2N3	111.6 (17)	C11—C12—H12A	119.9
S1—N3—H1N3	112 (2)	C13—C12—H12A	119.9
H2N3—N3—H1N3	116 (3)	C14—C13—C12	119.8 (2)
N1—C1—C2	125.4 (2)	C14—C13—H13A	120.1
N1—C1—H1A	117.3	C12—C13—H13A	120.1
C2—C1—H1A	117.3	C13—C14—C15	120.4 (2)
C3—C2—C1	119.9 (2)	C13—C14—S1	120.16 (17)
C3—C2—H2A	120.0	C15—C14—S1	119.35 (17)
C1—C2—H2A	120.0	C14—C15—C16	119.6 (2)
N2—C3—C2	123.6 (2)	C14—C15—H15A	120.2
N2—C3—C4	119.04 (19)	C16—C15—H15A	120.2
C2—C3—C4	117.38 (19)	C15—C16—C11	120.3 (2)
C5—C4—C9	118.1 (2)	C15—C16—H16A	119.8
C5—C4—C3	124.07 (19)	C11—C16—H16A	119.8
C9—C4—C3	117.80 (19)	C17—O3—H1O3	99.6
C6—C5—C4	121.6 (2)	O3—C17—H17A	110.6
C6—C5—H5A	119.2	O3—C17—H17B	106.9
C4—C5—H5A	119.2	H17A—C17—H17B	109.5
C5—C6—C7	119.9 (2)	O3—C17—H17C	110.9
C5—C6—H6A	120.1	H17A—C17—H17C	109.5
C7—C6—H6A	120.1	H17B—C17—H17C	109.5
C8—C7—C6	120.2 (2)	O4—C18—C19	122.6 (9)
C8—C7—C10	120.4 (2)	O4—C18—O4i	47.5 (5)
C6—C7—C10	119.3 (2)	C19—C18—O4i	167.5 (9)
C7—C8—C9	121.1 (2)	O4—C18—H18A	105.7
C7—C8—H8A	119.5	C19—C18—H18A	107.2
C9—C8—H8A	119.5	O4i—C18—H18A	72.6
N1—C9—C8	117.50 (19)	O4—C18—H18B	106.1
N1—C9—C4	123.32 (19)	C19—C18—H18B	107.9
C8—C9—C4	119.1 (2)	O4i—C18—H18B	83.8
F3B—C10—F1B	111.2 (9)	H18A—C18—H18B	106.3
F3B—C10—F1A	69.1 (7)	C18—C19—H19A	106.8
F1B—C10—F1A	124.4 (7)	C18—C19—H19B	110.5
F3B—C10—F2A	127.6 (7)	H19A—C19—H19B	109.5
F1A—C10—F2A	107.9 (8)	C18—C19—H19C	111.1
F3B—C10—F2B	102.5 (7)	H19A—C19—H19C	109.5
F1B—C10—F2B	105.4 (9)	H19B—C19—H19C	109.5
F2A—C10—F2B	81.8 (8)	O4i—O4—C18	80.7 (6)
F1B—C10—F3A	78.6 (8)	O4i—O4—C18i	51.8 (4)
F1A—C10—F3A	105.2 (7)	C18—O4—C18i	132.5 (5)
F2A—C10—F3A	102.4 (9)	C18—O4—H1O4	114.4
F2B—C10—F3A	133.7 (6)
C9—N1—C1—C2	0.9 (3)	C8—C7—C10—F1A	−2.1 (15)
N1—C1—C2—C3	−0.2 (4)	C6—C7—C10—F1A	174.3 (14)
C11—N2—C3—C2	1.4 (4)	C8—C7—C10—F2A	124.1 (7)
C11—N2—C3—C4	−178.6 (2)	C6—C7—C10—F2A	−59.5 (7)
C1—C2—C3—N2	178.6 (2)	C8—C7—C10—F2B	34.5 (10)
C1—C2—C3—C4	−1.4 (3)	C6—C7—C10—F2B	−149.1 (10)
N2—C3—C4—C5	3.9 (4)	C8—C7—C10—F3A	−121.4 (13)
C2—C3—C4—C5	−176.1 (2)	C6—C7—C10—F3A	55.0 (13)
N2—C3—C4—C9	−177.6 (2)	C3—N2—C11—C12	50.6 (4)
C2—C3—C4—C9	2.3 (3)	C3—N2—C11—C16	−130.4 (3)
C9—C4—C5—C6	0.2 (4)	C16—C11—C12—C13	2.5 (4)
C3—C4—C5—C6	178.7 (2)	N2—C11—C12—C13	−178.6 (2)
C4—C5—C6—C7	0.1 (4)	C11—C12—C13—C14	−2.0 (4)
C5—C6—C7—C8	0.6 (4)	C12—C13—C14—C15	−0.4 (4)
C5—C6—C7—C10	−175.8 (3)	C12—C13—C14—S1	176.73 (17)
C6—C7—C8—C9	−1.5 (4)	O2—S1—C14—C13	5.9 (2)
C10—C7—C8—C9	174.9 (2)	O1—S1—C14—C13	135.11 (19)
C1—N1—C9—C8	178.0 (2)	N3—S1—C14—C13	−110.4 (2)
C1—N1—C9—C4	0.2 (3)	O2—S1—C14—C15	−176.9 (2)
C7—C8—C9—N1	−176.2 (2)	O1—S1—C14—C15	−47.8 (2)
C7—C8—C9—C4	1.7 (3)	N3—S1—C14—C15	66.7 (2)
C5—C4—C9—N1	176.8 (2)	C13—C14—C15—C16	2.2 (4)
C3—C4—C9—N1	−1.8 (3)	S1—C14—C15—C16	−175.0 (2)
C5—C4—C9—C8	−1.0 (3)	C14—C15—C16—C11	−1.6 (4)
C3—C4—C9—C8	−179.6 (2)	C12—C11—C16—C15	−0.7 (4)
C8—C7—C10—F3B	−79.2 (13)	N2—C11—C16—C15	−179.7 (2)
C6—C7—C10—F3B	97.2 (13)	C19—C18—O4—O4i	−170.3 (9)
C8—C7—C10—F1B	152.4 (15)	C19—C18—O4—C18i	−170.3 (9)
C6—C7—C10—F1B	−31.2 (16)	O4i—C18—O4—C18i	−0.003 (1)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O3	0.87	2.21	3.016 (6)	153
N3—H2N3···N1ii	0.85 (3)	2.08 (3)	2.924 (3)	169 (3)
N3—H1N3···O1iii	0.87 (3)	2.26 (3)	3.107 (3)	163 (3)
O3—H1O3···O1iv	0.96	2.49	3.387 (6)	155
O3—H1O3···O2iv	0.96	2.59	3.425 (6)	146
C5—H5A···O1iv	0.93	2.50	3.343 (3)	151
C16—H16A···O3	0.93	2.51	3.287 (6)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O3	0.87	2.21	3.016 (6)	153
N3—H2N3⋯N1i	0.85 (3)	2.08 (3)	2.924 (3)	169 (3)
N3—H1N3⋯O1ii	0.87 (3)	2.26 (3)	3.107 (3)	163 (3)
O3—H1O3⋯O1iii	0.96	2.49	3.387 (6)	155
O3—H1O3⋯O2iii	0.96	2.59	3.425 (6)	146
C5—H5A⋯O1iii	0.93	2.50	3.343 (3)	151
C16—H16A⋯O3	0.93	2.51	3.287 (6)	141

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