3-Cyclo­hexyl­amino­propane-1-sulfonic acid hemihydrate

The biological buffer 3-cyclo­hexyl­amino­propane-1-sulfonic acid (CAPS, C₉H₁₉NO₃S) crystallizes in the space group C2/c with two CAPS mol­ecules and one water mol­ecule in the asymmetric unit. As is the case for other amino­sulfonic acids, CAPS is a zwitterion. Mol­ecules are linked into hydrogen-bonded dimers by inter­actions involving one of the amine protons and sulfonic acid O atoms, and these dimers are further linked through hydrogen bonding via the water mol­ecule to form layers. These layers are linked by out-of-plane hydrogen bonds involving the other amine proton.

Key indicators

• Single-crystal X-ray study
• T = 103 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.033
• wR factor = 0.085
• Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         40
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C9 H19 N O3 S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus and XPREP (Bruker, 2005); program(s) used to solve structure: SHELXTL (Bruker 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

3-cyclohexylaminopropane-1-sulfonic acid hemihydrate

Crystal data

C9H19NO3S·0.5H2O	F(000) = 2000
Mr = 230.32	Dx = 1.342 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7367 reflections
a = 29.2675 (17) Å	θ = 2.5–26.7°
b = 8.1613 (4) Å	µ = 0.27 mm^−1
c = 19.0984 (11) Å	T = 103 K
β = 92.206 (2)°	Block, colorless
V = 4558.5 (4) Å^3	0.59 × 0.25 × 0.20 mm
Z = 16

Data collection

Bruker APEX-II CCD diffractometer	4813 independent reflections
Radiation source: fine-focus sealed tube	4297 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 26.7°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −36→36
Tmin = 0.855, Tmax = 0.947	k = −10→8
20375 measured reflections	l = −24→24

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0409P)^2 + 4.8323P] where P = (Fo^2 + 2Fc^2)/3
4813 reflections	(Δ/σ)max = 0.001
268 parameters	Δρmax = 0.52 e Å^−3
3 restraints	Δρmin = −0.39 e Å^−3

Special details

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.

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 > σ(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.

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

	x	y	z	Uiso*/Ueq
S1A	0.459860 (11)	0.33601 (4)	0.099768 (17)	0.01212 (9)
S1B	0.598850 (11)	−0.17871 (4)	0.198158 (17)	0.01187 (9)
O1A	0.44727 (3)	0.49339 (12)	0.12872 (5)	0.0176 (2)
O2A	0.44587 (4)	0.31377 (15)	0.02657 (5)	0.0240 (3)
O3A	0.44499 (3)	0.20012 (12)	0.14439 (5)	0.0159 (2)
O1B	0.64140 (3)	−0.21641 (14)	0.16502 (5)	0.0210 (2)
O2B	0.59709 (4)	−0.01685 (13)	0.22959 (5)	0.0204 (2)
O3B	0.58598 (3)	−0.30605 (12)	0.24869 (5)	0.0135 (2)
O1W	0.35863 (5)	0.42664 (19)	−0.03730 (7)	0.0416 (3)
H1W1	0.3822 (7)	0.392 (3)	−0.0164 (11)	0.062*
H1W2	0.3537 (8)	0.358 (3)	−0.0688 (11)	0.062*
N1A	0.60980 (4)	0.35863 (15)	0.25250 (6)	0.0128 (2)
H1AC	0.5923	0.2928	0.2800	0.015*
H1AD	0.6043	0.4654	0.2652	0.015*
N1B	0.42648 (4)	−0.13911 (15)	0.12386 (6)	0.0121 (2)
H1BC	0.4237	−0.0329	0.1393	0.015*
H1BD	0.4250	−0.2062	0.1624	0.015*
C1A	0.52081 (4)	0.32706 (18)	0.10229 (7)	0.0143 (3)
H1AA	0.5306	0.2213	0.0824	0.017*
H1AB	0.5327	0.4160	0.0728	0.017*
C2A	0.54117 (5)	0.34402 (18)	0.17645 (7)	0.0139 (3)
H2AA	0.5294	0.2547	0.2059	0.017*
H2AB	0.5313	0.4495	0.1965	0.017*
C3A	0.59332 (4)	0.33742 (18)	0.17829 (7)	0.0132 (3)
H3AA	0.6038	0.2308	0.1600	0.016*
H3AB	0.6056	0.4258	0.1489	0.016*
C4A	0.65945 (4)	0.32139 (17)	0.26998 (7)	0.0135 (3)
H4AA	0.6654	0.2032	0.2598	0.016*
C5A	0.66754 (5)	0.35144 (19)	0.34842 (7)	0.0161 (3)
H5AA	0.6479	0.2768	0.3749	0.019*
H5AB	0.6589	0.4655	0.3596	0.019*
C6A	0.71770 (5)	0.3231 (2)	0.37111 (8)	0.0197 (3)
H6AA	0.7223	0.3499	0.4214	0.024*
H6AB	0.7255	0.2061	0.3647	0.024*
C7A	0.74923 (5)	0.4289 (2)	0.32830 (8)	0.0200 (3)
H7AA	0.7815	0.4040	0.3418	0.024*
H7AB	0.7436	0.5460	0.3384	0.024*
C8A	0.74100 (5)	0.3973 (2)	0.25009 (8)	0.0185 (3)
H8AA	0.7494	0.2827	0.2395	0.022*
H8AB	0.7609	0.4703	0.2233	0.022*
C9A	0.69092 (5)	0.42666 (19)	0.22640 (7)	0.0158 (3)
H9AA	0.6832	0.5439	0.2322	0.019*
H9AB	0.6865	0.3984	0.1762	0.019*
C1B	0.55596 (4)	−0.18533 (18)	0.12968 (7)	0.0139 (3)
H1BA	0.5626	−0.1001	0.0946	0.017*
H1BB	0.5572	−0.2931	0.1061	0.017*
C2B	0.50793 (4)	−0.15862 (18)	0.15525 (7)	0.0134 (3)
H2BA	0.5067	−0.0528	0.1804	0.016*
H2BB	0.5004	−0.2467	0.1885	0.016*
C3B	0.47276 (4)	−0.15811 (18)	0.09442 (7)	0.0126 (3)
H3BA	0.4789	−0.0664	0.0622	0.015*
H3BB	0.4744	−0.2620	0.0679	0.015*
C4B	0.38593 (4)	−0.17650 (17)	0.07551 (7)	0.0120 (3)
H4BA	0.3867	−0.2952	0.0626	0.014*
C5B	0.38719 (5)	−0.07462 (18)	0.00896 (7)	0.0148 (3)
H5BA	0.4148	−0.1030	−0.0169	0.018*
H5BB	0.3889	0.0431	0.0212	0.018*
C6B	0.34427 (5)	−0.1067 (2)	−0.03767 (7)	0.0180 (3)
H6BA	0.3450	−0.0369	−0.0800	0.022*
H6BB	0.3439	−0.2227	−0.0529	0.022*
C7B	0.30116 (5)	−0.0700 (2)	0.00170 (7)	0.0198 (3)
H7BA	0.2739	−0.0943	−0.0287	0.024*
H7BB	0.3004	0.0478	0.0141	0.024*
C8B	0.30005 (5)	−0.1732 (2)	0.06817 (8)	0.0211 (3)
H8BA	0.2984	−0.2907	0.0554	0.025*
H8BB	0.2724	−0.1456	0.0940	0.025*
C9B	0.34263 (5)	−0.14290 (19)	0.11549 (7)	0.0165 (3)
H9BA	0.3428	−0.0279	0.1320	0.020*
H9BB	0.3420	−0.2154	0.1570	0.020*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.01151 (16)	0.01340 (19)	0.01141 (17)	−0.00142 (12)	−0.00008 (12)	−0.00100 (13)
S1B	0.01107 (16)	0.01246 (18)	0.01195 (16)	−0.00150 (12)	−0.00116 (12)	0.00202 (13)
O1A	0.0176 (5)	0.0120 (5)	0.0235 (5)	0.0004 (4)	0.0018 (4)	0.0013 (4)
O2A	0.0179 (5)	0.0406 (7)	0.0134 (5)	−0.0037 (5)	−0.0023 (4)	−0.0032 (5)
O3A	0.0158 (5)	0.0114 (5)	0.0208 (5)	−0.0017 (4)	0.0026 (4)	−0.0002 (4)
O1B	0.0112 (5)	0.0331 (7)	0.0188 (5)	0.0004 (4)	0.0016 (4)	0.0044 (5)
O2B	0.0254 (6)	0.0121 (5)	0.0230 (5)	−0.0037 (4)	−0.0063 (4)	0.0015 (4)
O3B	0.0169 (5)	0.0114 (5)	0.0121 (5)	−0.0003 (4)	−0.0001 (4)	0.0013 (4)
O1W	0.0429 (8)	0.0463 (9)	0.0352 (7)	0.0177 (7)	−0.0048 (6)	−0.0039 (7)
N1A	0.0118 (5)	0.0131 (6)	0.0135 (6)	0.0005 (4)	0.0001 (4)	0.0003 (5)
N1B	0.0119 (5)	0.0131 (6)	0.0113 (5)	−0.0005 (4)	−0.0003 (4)	0.0003 (4)
C1A	0.0110 (6)	0.0182 (8)	0.0137 (7)	−0.0018 (5)	0.0019 (5)	−0.0016 (5)
C2A	0.0134 (6)	0.0152 (7)	0.0129 (6)	−0.0011 (5)	0.0000 (5)	−0.0010 (5)
C3A	0.0135 (6)	0.0135 (7)	0.0127 (6)	−0.0005 (5)	−0.0002 (5)	0.0006 (5)
C4A	0.0099 (6)	0.0128 (7)	0.0177 (7)	0.0015 (5)	−0.0003 (5)	0.0000 (5)
C5A	0.0138 (7)	0.0183 (8)	0.0163 (7)	−0.0003 (6)	0.0003 (5)	0.0011 (6)
C6A	0.0158 (7)	0.0227 (8)	0.0203 (7)	0.0011 (6)	−0.0043 (5)	0.0017 (6)
C7A	0.0135 (7)	0.0228 (8)	0.0233 (7)	−0.0008 (6)	−0.0023 (5)	−0.0019 (6)
C8A	0.0125 (7)	0.0199 (8)	0.0232 (7)	−0.0001 (6)	0.0028 (5)	−0.0018 (6)
C9A	0.0133 (7)	0.0175 (8)	0.0166 (7)	−0.0009 (5)	0.0017 (5)	0.0010 (6)
C1B	0.0120 (6)	0.0186 (8)	0.0110 (6)	0.0006 (5)	−0.0002 (5)	0.0013 (5)
C2B	0.0122 (6)	0.0152 (7)	0.0126 (6)	0.0003 (5)	−0.0005 (5)	−0.0002 (5)
C3B	0.0106 (6)	0.0136 (7)	0.0135 (6)	0.0000 (5)	0.0006 (5)	0.0014 (5)
C4B	0.0112 (6)	0.0122 (7)	0.0124 (6)	−0.0022 (5)	−0.0023 (5)	−0.0002 (5)
C5B	0.0139 (6)	0.0170 (7)	0.0136 (6)	0.0000 (5)	0.0002 (5)	0.0030 (6)
C6B	0.0177 (7)	0.0231 (8)	0.0129 (7)	−0.0003 (6)	−0.0027 (5)	0.0020 (6)
C7B	0.0142 (7)	0.0254 (8)	0.0193 (7)	−0.0001 (6)	−0.0044 (5)	0.0013 (6)
C8B	0.0118 (7)	0.0314 (9)	0.0199 (7)	−0.0040 (6)	−0.0008 (5)	0.0012 (6)
C9B	0.0128 (7)	0.0233 (8)	0.0132 (6)	−0.0015 (6)	0.0004 (5)	0.0017 (6)

Geometric parameters (Å, º)

S1A—O1A	1.4515 (11)	C6A—H6AB	0.990
S1A—O2A	1.4528 (10)	C7A—C8A	1.526 (2)
S1A—O3A	1.4745 (10)	C7A—H7AA	0.990
S1A—C1A	1.7842 (13)	C7A—H7AB	0.990
N1A—C3A	1.4894 (17)	C8A—C9A	1.5359 (19)
N1A—C4A	1.5093 (16)	C8A—H8AA	0.990
S1B—O1B	1.4514 (10)	C8A—H8AB	0.990
S1B—O2B	1.4527 (11)	C9A—H9AA	0.990
S1B—O3B	1.4769 (10)	C9A—H9AB	0.990
S1B—C1B	1.7785 (13)	C1B—C2B	1.5214 (18)
O1W—H1W1	0.832 (16)	C1B—H1BA	0.990
O1W—H1W2	0.829 (16)	C1B—H1BB	0.990
N1B—C3B	1.4944 (16)	C2B—C3B	1.5222 (18)
N1B—C4B	1.5066 (16)	C2B—H2BA	0.990
N1A—H1AC	0.920	C2B—H2BB	0.990
N1A—H1AD	0.920	C3B—H3BA	0.990
N1B—H1BC	0.920	C3B—H3BB	0.990
N1B—H1BD	0.920	C4B—C5B	1.5205 (19)
C1A—C2A	1.5216 (18)	C4B—C9B	1.5292 (18)
C1A—H1AA	0.990	C4B—H4BA	1.000
C1A—H1AB	0.990	C5B—C6B	1.5340 (18)
C2A—C3A	1.5265 (18)	C5B—H5BA	0.990
C2A—H2AA	0.990	C5B—H5BB	0.990
C2A—H2AB	0.990	C6B—C7B	1.523 (2)
C3A—H3AA	0.990	C6B—H6BA	0.990
C3A—H3AB	0.990	C6B—H6BB	0.990
C4A—C5A	1.5274 (19)	C7B—C8B	1.525 (2)
C4A—C9A	1.5292 (19)	C7B—H7BA	0.990
C4A—H4AA	1.000	C7B—H7BB	0.990
C5A—C6A	1.5324 (19)	C8B—C9B	1.5312 (19)
C5A—H5AA	0.990	C8B—H8BA	0.990
C5A—H5AB	0.990	C8B—H8BB	0.990
C6A—C7A	1.525 (2)	C9B—H9BA	0.990
C6A—H6AA	0.990	C9B—H9BB	0.990
O1A—S1A—O2A	114.26 (7)	C7A—C8A—C9A	112.01 (12)
O1A—S1A—O3A	111.13 (6)	C7A—C8A—H8AA	109.2
O2A—S1A—O3A	112.56 (6)	C9A—C8A—H8AA	109.2
O1A—S1A—C1A	107.10 (6)	C7A—C8A—H8AB	109.2
O2A—S1A—C1A	105.38 (6)	C9A—C8A—H8AB	109.2
O3A—S1A—C1A	105.70 (6)	H8AA—C8A—H8AB	107.9
C3A—N1A—C4A	117.44 (10)	C4A—C9A—C8A	109.88 (12)
O1B—S1B—O2B	114.69 (7)	C4A—C9A—H9AA	109.7
O1B—S1B—O3B	112.36 (6)	C8A—C9A—H9AA	109.7
O2B—S1B—O3B	110.84 (6)	C4A—C9A—H9AB	109.7
O1B—S1B—C1B	105.43 (6)	C8A—C9A—H9AB	109.7
O2B—S1B—C1B	107.23 (6)	H9AA—C9A—H9AB	108.2
O3B—S1B—C1B	105.59 (6)	C2B—C1B—S1B	113.22 (9)
C3B—N1B—C4B	116.89 (10)	C2B—C1B—H1BA	108.9
H1W1—O1W—H1W2	104 (2)	S1B—C1B—H1BA	108.9
C3A—N1A—H1AC	107.9	C2B—C1B—H1BB	108.9
C4A—N1A—H1AC	107.9	S1B—C1B—H1BB	108.9
C3A—N1A—H1AD	107.9	H1BA—C1B—H1BB	107.7
C4A—N1A—H1AD	107.9	C1B—C2B—C3B	111.18 (11)
H1AC—N1A—H1AD	107.2	C1B—C2B—H2BA	109.4
C3B—N1B—H1BC	108.1	C3B—C2B—H2BA	109.4
C4B—N1B—H1BC	108.1	C1B—C2B—H2BB	109.4
C3B—N1B—H1BD	108.1	C3B—C2B—H2BB	109.4
C4B—N1B—H1BD	108.1	H2BA—C2B—H2BB	108.0
H1BC—N1B—H1BD	107.3	N1B—C3B—C2B	108.01 (10)
C2A—C1A—S1A	112.13 (9)	N1B—C3B—H3BA	110.1
C2A—C1A—H1AA	109.2	C2B—C3B—H3BA	110.1
S1A—C1A—H1AA	109.2	N1B—C3B—H3BB	110.1
C2A—C1A—H1AB	109.2	C2B—C3B—H3BB	110.1
S1A—C1A—H1AB	109.2	H3BA—C3B—H3BB	108.4
H1AA—C1A—H1AB	107.9	N1B—C4B—C5B	110.97 (11)
C1A—C2A—C3A	111.94 (11)	N1B—C4B—C9B	107.82 (10)
C1A—C2A—H2AA	109.2	C5B—C4B—C9B	111.49 (11)
C3A—C2A—H2AA	109.2	N1B—C4B—H4BA	108.8
C1A—C2A—H2AB	109.2	C5B—C4B—H4BA	108.8
C3A—C2A—H2AB	109.2	C9B—C4B—H4BA	108.8
H2AA—C2A—H2AB	107.9	C4B—C5B—C6B	110.27 (11)
N1A—C3A—C2A	107.74 (10)	C4B—C5B—H5BA	109.6
N1A—C3A—H3AA	110.2	C6B—C5B—H5BA	109.6
C2A—C3A—H3AA	110.2	C4B—C5B—H5BB	109.6
N1A—C3A—H3AB	110.2	C6B—C5B—H5BB	109.6
C2A—C3A—H3AB	110.2	H5BA—C5B—H5BB	108.1
H3AA—C3A—H3AB	108.5	C7B—C6B—C5B	110.79 (11)
N1A—C4A—C5A	107.23 (11)	C7B—C6B—H6BA	109.5
N1A—C4A—C9A	111.19 (11)	C5B—C6B—H6BA	109.5
C5A—C4A—C9A	111.70 (11)	C7B—C6B—H6BB	109.5
N1A—C4A—H4AA	108.9	C5B—C6B—H6BB	109.5
C5A—C4A—H4AA	108.9	H6BA—C6B—H6BB	108.1
C9A—C4A—H4AA	108.9	C6B—C7B—C8B	110.29 (12)
C4A—C5A—C6A	111.33 (12)	C6B—C7B—H7BA	109.6
C4A—C5A—H5AA	109.4	C8B—C7B—H7BA	109.6
C6A—C5A—H5AA	109.4	C6B—C7B—H7BB	109.6
C4A—C5A—H5AB	109.4	C8B—C7B—H7BB	109.6
C6A—C5A—H5AB	109.4	H7BA—C7B—H7BB	108.1
H5AA—C5A—H5AB	108.0	C7B—C8B—C9B	111.04 (12)
C7A—C6A—C5A	110.84 (12)	C7B—C8B—H8BA	109.4
C7A—C6A—H6AA	109.5	C9B—C8B—H8BA	109.4
C5A—C6A—H6AA	109.5	C7B—C8B—H8BB	109.4
C7A—C6A—H6AB	109.5	C9B—C8B—H8BB	109.4
C5A—C6A—H6AB	109.5	H8BA—C8B—H8BB	108.0
H6AA—C6A—H6AB	108.1	C4B—C9B—C8B	110.35 (11)
C6A—C7A—C8A	110.67 (12)	C4B—C9B—H9BA	109.6
C6A—C7A—H7AA	109.5	C8B—C9B—H9BA	109.6
C8A—C7A—H7AA	109.5	C4B—C9B—H9BB	109.6
C6A—C7A—H7AB	109.5	C8B—C9B—H9BB	109.6
C8A—C7A—H7AB	109.5	H9BA—C9B—H9BB	108.1
H7AA—C7A—H7AB	108.1
O1A—S1A—C1A—C2A	59.46 (11)	O1B—S1B—C1B—C2B	176.53 (10)
O2A—S1A—C1A—C2A	−178.50 (10)	O2B—S1B—C1B—C2B	−60.84 (12)
O3A—S1A—C1A—C2A	−59.11 (11)	O3B—S1B—C1B—C2B	57.41 (12)
S1A—C1A—C2A—C3A	−179.63 (10)	S1B—C1B—C2B—C3B	177.57 (10)
C4A—N1A—C3A—C2A	167.48 (11)	C4B—N1B—C3B—C2B	−165.44 (11)
C1A—C2A—C3A—N1A	178.79 (11)	C1B—C2B—C3B—N1B	177.43 (11)
C3A—N1A—C4A—C5A	−179.71 (11)	C3B—N1B—C4B—C5B	−55.56 (15)
C3A—N1A—C4A—C9A	57.93 (16)	C3B—N1B—C4B—C9B	−177.93 (11)
N1A—C4A—C5A—C6A	−177.87 (11)	N1B—C4B—C5B—C6B	−176.68 (11)
C9A—C4A—C5A—C6A	−55.81 (16)	C9B—C4B—C5B—C6B	−56.47 (15)
C4A—C5A—C6A—C7A	55.73 (17)	C4B—C5B—C6B—C7B	57.21 (16)
C5A—C6A—C7A—C8A	−55.89 (17)	C5B—C6B—C7B—C8B	−57.69 (17)
C6A—C7A—C8A—C9A	56.70 (17)	C6B—C7B—C8B—C9B	57.36 (17)
N1A—C4A—C9A—C8A	174.88 (11)	N1B—C4B—C9B—C8B	178.09 (12)
C5A—C4A—C9A—C8A	55.14 (16)	C5B—C4B—C9B—C8B	56.05 (16)
C7A—C8A—C9A—C4A	−55.86 (16)	C7B—C8B—C9B—C4B	−56.26 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O2A	0.83 (2)	2.11 (2)	2.9354 (17)	173 (3)
O1W—H1W2···O1B^i	0.83 (2)	2.18 (2)	2.9821 (18)	162 (2)
N1A—H1AC···O3A^ii	0.92	1.99	2.8924 (15)	165
N1A—H1AD···O3B^iii	0.92	1.96	2.8243 (16)	155
N1A—H1AD···O1A^ii	0.92	2.58	3.0721 (15)	114
N1B—H1BC···O3A	0.92	2.00	2.8453 (16)	152
N1B—H1BC···O2B^ii	0.92	2.60	3.0747 (15)	113
N1B—H1BD···O3B^ii	0.92	1.92	2.8253 (15)	167

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