Tetracycline hydrochloride: a synchrotron microcrystal study

The title compound, [(4S,4aS,5aS,6S,12aS)-2-amino­hydroxy­methyl­ene-1,2,3,4,4a,5,5a,6,11,12a-deca­hydro-6,10,12,12a-tetra­­hydroxy-6-methyl-1,3,11-trioxo­naphthacen-4-yl]­di­methyl­amm­onium chloride, C₂₂H₂₅N₂O₈⁺·Cl^-, a well known antibiotic, has been structurally characterized from an individual coarse powder grain by use of high-intensity synchrotron radiation, in conjunction with an exercise in ab initio powder diffraction structure solution. Free refinement of all H atoms establishes the major tautomeric form of the protonated tetracycline mol­ecule without prejudice. The mol­ecule has extensive intramolecular hydrogen bonding involving most of the potential donors and acceptors, and all intermolecular hydrogen bonding uses the chloride anion as acceptor.

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: local programs; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 1995); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

[(4S,4aS,5aS,6R,12aS)-2-aminohydroxymethylene-1,2,3,4,4a,5,5a,6,11,12a- decahydro-6,10,12,12a-tetrahydroxy-6-methyl-1,3,11-trioxonaphthacen-4-yl] dimethylammonium chloride

Crystal data

C22H25N2O8^+·Cl^−	Dx = 1.463 Mg m^−3
Mr = 480.89	Synchrotron radiation, λ = 0.6883 Å
Orthorhombic, P212121	Cell parameters from 6452 reflections
a = 10.9300 (9) Å	θ = 2.5–29.2°
b = 12.7162 (11) Å	µ = 0.23 mm^−1
c = 15.7085 (13) Å	T = 150 K
V = 2183.3 (3) Å^3	Prism, yellow
Z = 4	0.04 × 0.03 × 0.02 mm
F(000) = 1008

Data collection

Bruker SMART CCD diffractometer with Oxford Cryosystems open-flow cryostat (Cosier & Glazer, 1986)	3937 reflections with I > 2σ(I)
Radiation source: Daresbury SRS station 9.8	Rint = 0.047
Silicon 111 monochromator	θmax = 29.3°, θmin = 2.2°
Detector resolution: 8.192 pixels mm^-1	h = −14→8
ω rotation with narrow frames scans	k = −17→17
8955 measured reflections	l = −21→4
4915 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.050	w = 1/[σ^2(Fo^2) + (0.0579P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.116	(Δ/σ)max = 0.001
S = 0.97	Δρmax = 0.57 e Å^−3
4915 reflections	Δρmin = −0.24 e Å^−3
399 parameters	Extinction correction: SHELXTL (Sheldrick, 1995), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0038 (12)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983); 1958 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.02 (8)

Special details

Experimental. The data collection nominally covered over a quadrant of reciprocal space, by a combination of two sets of ω-scan exposures, each set with a different φ angle for the crystal and with frame widths of 0.15°. Crystal cooling was by a Cryostream device (Cosier & Glazer, 1986).

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

	x	y	z	Uiso*/Ueq
Cl1	0.92963 (7)	0.41939 (6)	−0.00197 (4)	0.01949 (17)
O1	0.0086 (3)	0.3656 (3)	0.43967 (14)	0.0392 (7)
H1	0.039 (4)	0.433 (4)	0.435 (2)	0.047 (13)*
O6	0.1453 (2)	0.46012 (16)	0.12979 (12)	0.0194 (5)
H6	0.086 (4)	0.449 (3)	0.088 (2)	0.045 (12)*
O11	0.7514 (2)	0.64335 (19)	0.07408 (14)	0.0268 (5)
O13	0.3634 (2)	0.71743 (18)	0.18883 (13)	0.0250 (5)
O14	0.5800 (2)	0.60174 (18)	0.29547 (12)	0.0212 (5)
H14	0.565 (4)	0.614 (3)	0.338 (2)	0.033 (11)*
O15	0.3506 (2)	0.60822 (17)	0.35612 (12)	0.0198 (5)
H15	0.283 (4)	0.580 (4)	0.385 (2)	0.045 (12)*
O17	0.1647 (2)	0.50211 (18)	0.38835 (12)	0.0234 (5)
O19	0.6623 (3)	0.81863 (18)	0.04211 (13)	0.0269 (6)
H19	0.734 (5)	0.757 (4)	0.055 (3)	0.061 (14)*
N10	0.7465 (3)	0.4488 (2)	0.14281 (16)	0.0193 (6)
H10	0.793 (4)	0.464 (3)	0.100 (2)	0.035 (11)*
N19	0.4694 (3)	0.8551 (2)	0.08138 (17)	0.0288 (7)
H19A	0.475 (4)	0.921 (3)	0.058 (2)	0.034 (10)*
H19B	0.408 (4)	0.833 (4)	0.112 (2)	0.049 (14)*
C1	0.0207 (3)	0.3204 (3)	0.36224 (18)	0.0272 (8)
C2	−0.0525 (4)	0.2345 (3)	0.3435 (2)	0.0314 (9)
H2	−0.111 (3)	0.211 (3)	0.388 (2)	0.026 (9)*
C3	−0.0436 (4)	0.1888 (3)	0.2657 (2)	0.0302 (8)
H3	−0.084 (4)	0.134 (3)	0.253 (2)	0.040 (12)*
C4	0.0378 (3)	0.2253 (3)	0.2036 (2)	0.0240 (7)
H4	0.038 (3)	0.189 (3)	0.148 (2)	0.028 (9)*
C5	0.1113 (3)	0.3105 (2)	0.22057 (18)	0.0183 (7)
C6	0.1962 (3)	0.3609 (2)	0.15436 (17)	0.0178 (7)
C7	0.3178 (3)	0.3872 (2)	0.19906 (16)	0.0145 (6)
H7	0.337 (4)	0.318 (3)	0.222 (2)	0.028 (9)*
C8	0.4148 (3)	0.4314 (2)	0.13903 (16)	0.0170 (6)
H8A	0.378 (4)	0.486 (3)	0.107 (2)	0.035 (10)*
H8B	0.444 (3)	0.378 (3)	0.1001 (19)	0.025 (9)*
C9	0.5241 (3)	0.4766 (2)	0.18811 (16)	0.0141 (6)
H9	0.554 (3)	0.423 (3)	0.2292 (18)	0.020 (8)*
C10	0.6283 (3)	0.5041 (2)	0.12622 (17)	0.0156 (6)
H10A	0.615 (3)	0.482 (2)	0.0715 (17)	0.007 (7)*
C11	0.6526 (3)	0.6204 (2)	0.11090 (16)	0.0180 (6)
C12	0.5579 (3)	0.6923 (2)	0.12673 (16)	0.0170 (6)
C13	0.4588 (3)	0.6663 (2)	0.18199 (15)	0.0171 (7)
C14	0.4828 (3)	0.5705 (2)	0.24083 (15)	0.0150 (6)
C15	0.3690 (3)	0.5439 (2)	0.29061 (15)	0.0158 (6)
C16	0.2940 (3)	0.4624 (2)	0.27178 (16)	0.0149 (6)
C17	0.1867 (3)	0.4446 (2)	0.32353 (16)	0.0184 (7)
C18	0.1060 (3)	0.3578 (3)	0.30253 (17)	0.0187 (7)
C19	0.5622 (3)	0.7911 (2)	0.08265 (16)	0.0204 (7)
C20	0.2161 (4)	0.2919 (3)	0.0769 (2)	0.0246 (8)
H20A	0.135 (3)	0.284 (3)	0.0479 (18)	0.015 (8)*
H20B	0.245 (4)	0.225 (4)	0.090 (2)	0.038 (11)*
H20C	0.259 (3)	0.329 (3)	0.034 (2)	0.025 (9)*
C21	0.7318 (4)	0.3324 (3)	0.1384 (2)	0.0259 (8)
H21A	0.688 (4)	0.311 (3)	0.184 (2)	0.041 (11)*
H21B	0.810 (4)	0.303 (3)	0.1312 (19)	0.019 (9)*
H21C	0.698 (3)	0.321 (3)	0.085 (2)	0.028 (10)*
C22	0.8096 (4)	0.4811 (3)	0.2228 (2)	0.0308 (9)
H22A	0.820 (3)	0.559 (3)	0.223 (2)	0.028 (9)*
H22B	0.885 (4)	0.458 (4)	0.222 (2)	0.039 (12)*
H22C	0.761 (4)	0.457 (3)	0.269 (2)	0.030 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0148 (4)	0.0225 (3)	0.0212 (3)	−0.0031 (3)	0.0017 (3)	0.0011 (3)
O1	0.0359 (18)	0.0553 (19)	0.0265 (11)	−0.0166 (16)	0.0098 (10)	0.0003 (11)
O6	0.0161 (13)	0.0172 (11)	0.0248 (10)	0.0042 (11)	−0.0052 (9)	0.0008 (8)
O11	0.0167 (14)	0.0226 (12)	0.0412 (11)	−0.0041 (11)	0.0086 (10)	0.0072 (10)
O13	0.0229 (15)	0.0233 (12)	0.0288 (10)	0.0096 (12)	0.0041 (9)	0.0014 (9)
O14	0.0140 (13)	0.0322 (13)	0.0174 (9)	−0.0055 (11)	−0.0032 (8)	−0.0005 (8)
O15	0.0154 (13)	0.0240 (12)	0.0200 (9)	0.0000 (11)	0.0013 (8)	−0.0047 (8)
O17	0.0180 (13)	0.0292 (12)	0.0229 (9)	0.0002 (12)	0.0037 (8)	−0.0026 (9)
O19	0.0310 (16)	0.0199 (12)	0.0297 (11)	−0.0075 (13)	−0.0002 (10)	0.0052 (9)
N10	0.0132 (15)	0.0194 (13)	0.0254 (11)	−0.0001 (12)	0.0046 (10)	0.0042 (10)
N19	0.038 (2)	0.0166 (14)	0.0319 (14)	0.0056 (15)	−0.0021 (13)	0.0069 (11)
C1	0.020 (2)	0.0351 (19)	0.0262 (14)	−0.0004 (17)	0.0011 (13)	0.0090 (13)
C2	0.017 (2)	0.041 (2)	0.0364 (16)	−0.0087 (19)	−0.0011 (14)	0.0125 (15)
C3	0.017 (2)	0.0267 (19)	0.0466 (18)	−0.0080 (19)	−0.0042 (14)	0.0057 (15)
C4	0.013 (2)	0.0218 (17)	0.0373 (16)	0.0003 (15)	−0.0020 (13)	−0.0007 (13)
C5	0.0084 (18)	0.0178 (15)	0.0287 (13)	0.0039 (14)	−0.0015 (11)	0.0034 (11)
C6	0.0169 (18)	0.0154 (14)	0.0211 (12)	0.0025 (14)	−0.0004 (11)	−0.0015 (10)
C7	0.0061 (16)	0.0135 (14)	0.0237 (12)	0.0009 (13)	0.0003 (10)	−0.0006 (10)
C8	0.0124 (17)	0.0177 (15)	0.0209 (11)	0.0008 (15)	0.0022 (11)	−0.0034 (11)
C9	0.0079 (16)	0.0132 (14)	0.0211 (11)	0.0007 (13)	0.0011 (10)	0.0015 (10)
C10	0.0074 (16)	0.0173 (15)	0.0220 (12)	0.0014 (14)	−0.0008 (10)	0.0011 (11)
C11	0.0153 (18)	0.0184 (15)	0.0202 (12)	−0.0003 (15)	−0.0013 (11)	0.0031 (11)
C12	0.0172 (18)	0.0133 (13)	0.0206 (12)	−0.0003 (15)	−0.0011 (11)	0.0006 (9)
C13	0.018 (2)	0.0167 (14)	0.0161 (11)	0.0002 (15)	−0.0013 (11)	−0.0034 (10)
C14	0.0119 (16)	0.0151 (14)	0.0181 (11)	−0.0015 (14)	−0.0024 (10)	−0.0005 (10)
C15	0.0135 (17)	0.0170 (15)	0.0170 (11)	0.0046 (14)	−0.0036 (10)	0.0015 (10)
C16	0.0123 (17)	0.0153 (14)	0.0172 (11)	0.0040 (14)	−0.0009 (10)	0.0024 (10)
C17	0.0151 (18)	0.0210 (16)	0.0190 (12)	0.0052 (15)	−0.0009 (10)	0.0038 (10)
C18	0.0111 (18)	0.0209 (16)	0.0240 (13)	0.0031 (14)	−0.0007 (11)	0.0045 (11)
C19	0.026 (2)	0.0143 (14)	0.0209 (12)	−0.0055 (17)	−0.0036 (12)	0.0000 (10)
C20	0.019 (2)	0.0250 (19)	0.0299 (15)	−0.0014 (18)	0.0012 (13)	−0.0109 (13)
C21	0.024 (2)	0.0177 (17)	0.0366 (17)	0.0050 (17)	0.0117 (15)	0.0046 (13)
C22	0.017 (2)	0.038 (2)	0.0367 (18)	0.002 (2)	−0.0056 (15)	0.0019 (15)

Geometric parameters (Å, º)

O1—C1	1.352 (4)	C6—C20	1.516 (4)
O1—H1	0.92 (5)	C6—C7	1.540 (4)
O6—C6	1.432 (4)	C7—C16	1.512 (4)
O6—H6	0.94 (4)	C7—C8	1.526 (4)
O11—C11	1.260 (4)	C7—H7	0.97 (4)
O13—C13	1.234 (4)	C8—C9	1.534 (4)
O14—C14	1.422 (3)	C8—H8A	0.95 (4)
O14—H14	0.70 (4)	C8—H8B	0.97 (3)
O15—C15	1.330 (3)	C9—C14	1.522 (4)
O15—H15	0.94 (4)	C9—C10	1.538 (4)
O17—C17	1.277 (3)	C9—H9	1.00 (3)
O19—C19	1.314 (4)	C10—C11	1.521 (4)
O19—H19	1.13 (5)	C10—H10A	0.92 (3)
N10—C21	1.490 (4)	C11—C12	1.403 (5)
N10—C22	1.490 (4)	C12—C13	1.427 (4)
N10—C10	1.494 (4)	C12—C19	1.435 (4)
N10—H10	0.87 (4)	C13—C14	1.551 (4)
N19—C19	1.301 (5)	C14—C15	1.507 (4)
N19—H19A	0.91 (4)	C15—C16	1.354 (4)
N19—H19B	0.86 (5)	C16—C17	1.445 (4)
C1—C2	1.386 (5)	C17—C18	1.450 (5)
C1—C18	1.405 (4)	C20—H20A	1.00 (3)
C2—C3	1.357 (5)	C20—H20B	0.93 (4)
C2—H2	1.00 (4)	C20—H20C	0.95 (4)
C3—C4	1.400 (5)	C21—H21A	0.90 (4)
C3—H3	0.85 (4)	C21—H21B	0.94 (4)
C4—C5	1.374 (5)	C21—H21C	0.92 (4)
C4—H4	0.99 (3)	C22—H22A	0.99 (4)
C5—C18	1.422 (4)	C22—H22B	0.88 (5)
C5—C6	1.534 (4)	C22—H22C	0.95 (4)
C1—O1—H1	107 (2)	N10—C10—C9	115.0 (2)
C6—O6—H6	109 (3)	C11—C10—C9	116.8 (3)
C14—O14—H14	117 (4)	N10—C10—H10A	99.4 (19)
C15—O15—H15	105 (3)	C11—C10—H10A	100.0 (19)
C19—O19—H19	108 (2)	C9—C10—H10A	113.8 (19)
C21—N10—C22	111.3 (3)	O11—C11—C12	124.2 (3)
C21—N10—C10	111.5 (3)	O11—C11—C10	116.6 (3)
C22—N10—C10	114.7 (3)	C12—C11—C10	118.5 (3)
C21—N10—H10	104 (3)	C11—C12—C13	121.1 (3)
C22—N10—H10	109 (3)	C11—C12—C19	117.5 (3)
C10—N10—H10	105 (3)	C13—C12—C19	121.4 (3)
C19—N19—H19A	121 (3)	O13—C13—C12	124.9 (3)
C19—N19—H19B	113 (3)	O13—C13—C14	120.3 (3)
H19A—N19—H19B	125 (4)	C12—C13—C14	114.6 (3)
O1—C1—C2	118.0 (3)	O14—C14—C15	111.5 (2)
O1—C1—C18	121.4 (3)	O14—C14—C9	109.0 (2)
C2—C1—C18	120.5 (3)	C15—C14—C9	110.5 (2)
C3—C2—C1	119.2 (3)	O14—C14—C13	105.5 (2)
C3—C2—H2	123 (2)	C15—C14—C13	110.2 (3)
C1—C2—H2	117 (2)	C9—C14—C13	110.0 (2)
C2—C3—C4	122.1 (4)	O15—C15—C16	123.2 (3)
C2—C3—H3	122 (3)	O15—C15—C14	112.8 (3)
C4—C3—H3	116 (3)	C16—C15—C14	123.9 (3)
C5—C4—C3	119.9 (3)	C15—C16—C17	119.3 (3)
C5—C4—H4	123 (2)	C15—C16—C7	123.0 (3)
C3—C4—H4	117 (2)	C17—C16—C7	117.7 (3)
C4—C5—C18	119.0 (3)	O17—C17—C16	120.8 (3)
C4—C5—C6	123.4 (3)	O17—C17—C18	120.2 (3)
C18—C5—C6	117.5 (3)	C16—C17—C18	119.0 (3)
O6—C6—C20	110.4 (2)	C1—C18—C5	119.2 (3)
O6—C6—C5	108.4 (3)	C1—C18—C17	120.6 (3)
C20—C6—C5	112.9 (3)	C5—C18—C17	120.2 (3)
O6—C6—C7	105.5 (2)	N19—C19—O19	118.4 (3)
C20—C6—C7	111.6 (3)	N19—C19—C12	122.0 (3)
C5—C6—C7	107.7 (2)	O19—C19—C12	119.6 (3)
C16—C7—C8	110.7 (2)	C6—C20—H20A	107.5 (18)
C16—C7—C6	109.5 (2)	C6—C20—H20B	114 (2)
C8—C7—C6	113.4 (2)	H20A—C20—H20B	108 (3)
C16—C7—H7	109 (2)	C6—C20—H20C	111 (2)
C8—C7—H7	114 (2)	H20A—C20—H20C	99 (3)
C6—C7—H7	99 (2)	H20B—C20—H20C	117 (3)
C7—C8—C9	111.6 (2)	N10—C21—H21A	109 (3)
C7—C8—H8A	108 (2)	N10—C21—H21B	108 (2)
C9—C8—H8A	109 (2)	H21A—C21—H21B	117 (3)
C7—C8—H8B	111 (2)	N10—C21—H21C	104 (2)
C9—C8—H8B	109 (2)	H21A—C21—H21C	117 (3)
H8A—C8—H8B	109 (3)	H21B—C21—H21C	101 (3)
C14—C9—C8	109.7 (2)	N10—C22—H22A	108.9 (19)
C14—C9—C10	112.6 (2)	N10—C22—H22B	110 (3)
C8—C9—C10	110.2 (2)	H22A—C22—H22B	103 (4)
C14—C9—H9	106.5 (18)	N10—C22—H22C	108 (2)
C8—C9—H9	109 (2)	H22A—C22—H22C	113 (3)
C10—C9—H9	109.1 (19)	H22B—C22—H22C	115 (3)
N10—C10—C11	109.5 (3)
O1—C1—C2—C3	178.9 (3)	C8—C9—C14—C15	48.5 (3)
C18—C1—C2—C3	−2.1 (5)	C10—C9—C14—C15	171.6 (2)
C1—C2—C3—C4	0.3 (6)	C8—C9—C14—C13	−73.4 (3)
C2—C3—C4—C5	−0.4 (5)	C10—C9—C14—C13	49.6 (3)
C3—C4—C5—C18	2.2 (5)	O13—C13—C14—O14	−110.9 (3)
C3—C4—C5—C6	−175.4 (3)	C12—C13—C14—O14	64.6 (3)
C4—C5—C6—O6	107.7 (3)	O13—C13—C14—C15	9.5 (4)
C18—C5—C6—O6	−69.9 (3)	C12—C13—C14—C15	−175.0 (2)
C4—C5—C6—C20	−15.0 (4)	O13—C13—C14—C9	131.7 (3)
C18—C5—C6—C20	167.5 (3)	C12—C13—C14—C9	−52.8 (3)
C4—C5—C6—C7	−138.7 (3)	O14—C14—C15—O15	38.9 (3)
C18—C5—C6—C7	43.8 (4)	C9—C14—C15—O15	160.3 (2)
O6—C6—C7—C16	55.9 (3)	C13—C14—C15—O15	−77.9 (3)
C20—C6—C7—C16	175.9 (3)	O14—C14—C15—C16	−140.3 (3)
C5—C6—C7—C16	−59.7 (3)	C9—C14—C15—C16	−18.8 (4)
O6—C6—C7—C8	−68.3 (3)	C13—C14—C15—C16	103.0 (3)
C20—C6—C7—C8	51.6 (4)	O15—C15—C16—C17	1.4 (4)
C5—C6—C7—C8	176.1 (3)	C14—C15—C16—C17	−179.6 (3)
C16—C7—C8—C9	45.2 (3)	O15—C15—C16—C7	−177.8 (3)
C6—C7—C8—C9	168.7 (2)	C14—C15—C16—C7	1.3 (4)
C7—C8—C9—C14	−64.4 (3)	C8—C7—C16—C15	−14.4 (4)
C7—C8—C9—C10	171.1 (3)	C6—C7—C16—C15	−140.2 (3)
C21—N10—C10—C11	−166.9 (2)	C8—C7—C16—C17	166.4 (3)
C22—N10—C10—C11	65.5 (3)	C6—C7—C16—C17	40.6 (3)
C21—N10—C10—C9	59.2 (3)	C15—C16—C17—O17	−2.7 (4)
C22—N10—C10—C9	−68.4 (3)	C7—C16—C17—O17	176.6 (3)
C14—C9—C10—N10	116.1 (3)	C15—C16—C17—C18	179.4 (3)
C8—C9—C10—N10	−121.1 (3)	C7—C16—C17—C18	−1.4 (4)
C14—C9—C10—C11	−14.3 (3)	O1—C1—C18—C5	−177.2 (3)
C8—C9—C10—C11	108.5 (3)	C2—C1—C18—C5	3.8 (5)
N10—C10—C11—O11	33.6 (3)	O1—C1—C18—C17	1.9 (5)
C9—C10—C11—O11	166.6 (2)	C2—C1—C18—C17	−177.1 (3)
N10—C10—C11—C12	−155.6 (2)	C4—C5—C18—C1	−3.8 (5)
C9—C10—C11—C12	−22.6 (4)	C6—C5—C18—C1	173.8 (3)
O11—C11—C12—C13	−168.4 (3)	C4—C5—C18—C17	177.1 (3)
C10—C11—C12—C13	21.5 (4)	C6—C5—C18—C17	−5.2 (4)
O11—C11—C12—C19	14.0 (4)	O17—C17—C18—C1	−14.8 (4)
C10—C11—C12—C19	−156.0 (3)	C16—C17—C18—C1	163.1 (3)
C11—C12—C13—O13	−168.0 (3)	O17—C17—C18—C5	164.3 (3)
C19—C12—C13—O13	9.5 (4)	C16—C17—C18—C5	−17.8 (4)
C11—C12—C13—C14	16.7 (4)	C11—C12—C19—N19	167.9 (3)
C19—C12—C13—C14	−165.8 (2)	C13—C12—C19—N19	−9.6 (4)
C8—C9—C14—O14	171.4 (2)	C11—C12—C19—O19	−12.1 (4)
C10—C9—C14—O14	−65.6 (3)	C13—C12—C19—O19	170.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O17	0.92 (5)	1.79 (5)	2.564 (4)	140 (4)
O6—H6···Cl1^i	0.94 (4)	2.25 (4)	3.179 (2)	174 (3)
O14—H14···O15	0.70 (4)	2.36 (4)	2.683 (3)	110 (4)
O14—H14···Cl1^ii	0.70 (4)	2.56 (4)	3.195 (2)	153 (4)
O15—H15···O17	0.94 (4)	1.63 (5)	2.491 (3)	151 (4)
O19—H19···O11	1.13 (5)	1.49 (5)	2.484 (3)	143 (4)
N10—H10···Cl1	0.87 (4)	2.26 (4)	3.053 (3)	152 (3)
N19—H19A···Cl1^iii	0.91 (4)	2.27 (4)	3.157 (3)	163 (4)
N19—H19B···O13	0.86 (5)	1.97 (5)	2.694 (4)	141 (4)

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