Dibrucinium sulfate hepta­hydrate

The crystal structure of dibrucinium sulfate­(VI) hepta­hydrate, 2C₂₃H₂₇N₂O₄⁺·SO₄²⁻·7H₂O, has been determined. The components are packed in layers. Puckered brucinium sheets are separated by layers consisting of hydrogen-bonded disordered sulfate(VI) anions and water mol­ecules. Both layers, the cationic together with the anionic/water, are linked by N—H⁺...O⁻ and O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in solvent or counterion
• R factor = 0.047
• wR factor = 0.094
• Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H21W   ..  H42W    ..       1.90 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      31.00 Perc.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.99
           From the CIF: _reflns_number_total               4939
           Count of symmetry unique reflns         2791
           Completeness (_total/calc)            176.96%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2148
           Fraction of Friedel pairs measured     0.770
           Are heavy atom types Z>Si present        yes

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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

---

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2001); cell refinement: CrysAlis RED (Oxford Diffraction, 2001); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT (Bruker, 1999); software used to prepare material for publication: SHELXL97.

Dibrucinium sulfate heptahydrate

Crystal data

2C23H27N2O4^+·SO4^2^−·7H2O	F(000) = 2160
Mr = 1013.10	Dx = 1.455 Mg m^−3
Orthorhombic, C2221	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c 2	Cell parameters from 5256 reflections
a = 12.1765 (9) Å	θ = 3.7–28.5°
b = 14.2518 (10) Å	µ = 0.16 mm^−1
c = 26.6488 (18) Å	T = 100 K
V = 4624.6 (6) Å^3	Block, colourless
Z = 4	0.40 × 0.40 × 0.40 mm

Data collection

Kuma KM4 CCD area-detector diffractometer	4393 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.043
Graphite monochromator	θmax = 27.0°, θmin = 3.7°
ω scans	h = −15→15
15405 measured reflections	k = −18→17
4939 independent reflections	l = −33→19

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.043P)^2 + 1.9728P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
4939 reflections	Δρmax = 0.22 e Å^−3
335 parameters	Δρmin = −0.27 e Å^−3
0 restraints	Absolute structure: Toda et al. (1985) and Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (9)

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	Occ. (<1)
O1	0.54403 (13)	0.30905 (12)	0.10757 (6)	0.0255 (4)
O2	−0.04385 (12)	0.43000 (11)	−0.06702 (5)	0.0197 (3)
O3	−0.15923 (12)	0.38403 (11)	0.01099 (6)	0.0206 (4)
O4	0.36636 (13)	0.41266 (11)	−0.03854 (6)	0.0220 (4)
N1	0.28858 (14)	0.32578 (13)	0.02409 (7)	0.0174 (4)
N2	0.19748 (16)	0.17928 (17)	0.17234 (7)	0.0308 (5)
H2	0.1362	0.1542	0.1908	0.037*
C1	0.12701 (18)	0.38100 (15)	−0.02813 (8)	0.0170 (5)
H1	0.1702	0.4011	−0.0558	0.020*
C2	0.01389 (19)	0.39191 (14)	−0.02786 (8)	0.0170 (5)
C3	−0.04967 (17)	0.36429 (15)	0.01388 (8)	0.0169 (5)
C4	−0.0003 (2)	0.31886 (15)	0.05400 (8)	0.0191 (4)
H4	−0.0432	0.2965	0.0813	0.023*
C5	0.11303 (18)	0.30654 (16)	0.05366 (8)	0.0188 (5)
C6	0.17475 (17)	0.33953 (15)	0.01367 (8)	0.0163 (5)
C7	0.18417 (18)	0.25377 (17)	0.09034 (9)	0.0217 (5)
C8	0.30151 (18)	0.28741 (16)	0.07578 (8)	0.0188 (5)
H8	0.3528	0.2327	0.0752	0.023*
C9	0.37313 (18)	0.37408 (15)	0.00289 (9)	0.0186 (5)
C10	0.47825 (18)	0.37518 (16)	0.03282 (8)	0.0214 (5)
H10A	0.5223	0.4296	0.0214	0.026*
H10B	0.5202	0.3179	0.0241	0.026*
C11	0.46962 (19)	0.38020 (17)	0.09081 (9)	0.0238 (5)
H11	0.4960	0.4429	0.1026	0.029*
C12	0.5615 (2)	0.3049 (2)	0.16117 (10)	0.0327 (6)
H12A	0.5554	0.3688	0.1755	0.039*
H12B	0.6364	0.2812	0.1681	0.039*
C13	0.4790 (2)	0.24207 (19)	0.18547 (9)	0.0293 (6)
H13	0.5034	0.1860	0.2012	0.035*
C14	0.3732 (2)	0.26213 (18)	0.18572 (9)	0.0267 (6)
C15	0.2899 (2)	0.1970 (2)	0.20866 (9)	0.0338 (7)
H15A	0.2603	0.2252	0.2398	0.041*
H15B	0.3255	0.1368	0.2175	0.041*
C16	0.2276 (2)	0.10964 (18)	0.13187 (9)	0.0273 (6)
H16A	0.2000	0.0462	0.1402	0.033*
H16B	0.3083	0.1066	0.1274	0.033*
C17	0.17241 (19)	0.14704 (17)	0.08511 (9)	0.0258 (6)
H17A	0.0941	0.1284	0.0839	0.031*
H17B	0.2097	0.1241	0.0545	0.031*
C18	0.35045 (19)	0.36591 (17)	0.10752 (8)	0.0222 (5)
H18	0.3105	0.4243	0.0975	0.027*
C19	0.3279 (2)	0.35323 (19)	0.16393 (9)	0.0293 (6)
H19	0.3603	0.4074	0.1826	0.035*
C20	0.2029 (2)	0.3544 (2)	0.17057 (9)	0.0339 (7)
H20A	0.1843	0.3550	0.2067	0.041*
H20B	0.1719	0.4117	0.1550	0.041*
C21	0.1546 (2)	0.26868 (19)	0.14611 (9)	0.0297 (6)
H21	0.0729	0.2710	0.1495	0.036*
C22	0.0201 (2)	0.46212 (17)	−0.10871 (8)	0.0245 (5)
H22A	−0.0287	0.4879	−0.1345	0.037*
H22B	0.0618	0.4095	−0.1228	0.037*
H22C	0.0711	0.5110	−0.0974	0.037*
C23	−0.22143 (18)	0.37021 (19)	0.05599 (9)	0.0254 (5)
H23A	−0.2985	0.3864	0.0498	0.038*
H23B	−0.1921	0.4104	0.0826	0.038*
H23C	−0.2163	0.3044	0.0663	0.038*
S1	0.0000	0.06892 (6)	0.2500	0.01920 (17)
O5	0.0093 (3)	0.0658 (2)	0.19580 (10)	0.0215 (7)	0.50
O6	−0.0198 (3)	0.1691 (2)	0.26651 (11)	0.0248 (7)	0.50
O7	−0.0890 (3)	0.0116 (3)	0.26944 (14)	0.0315 (8)	0.50
O8	0.1087 (3)	0.0390 (2)	0.27217 (13)	0.0287 (8)	0.50
O1W	0.0000	0.5356 (2)	0.2500	0.0595 (9)
H11W	0.0447	0.4933	0.2630	0.020*
O2W	0.12986 (16)	0.27896 (13)	0.31405 (8)	0.0421 (5)
H21W	0.1510	0.2285	0.3306	0.063*
H22W	0.0798	0.2610	0.2922	0.063*
O3W	0.19672 (17)	0.45654 (14)	0.28801 (8)	0.0432 (5)
H31W	0.1870	0.3963	0.2941	0.065*
H32W	0.2600	0.4622	0.2723	0.065*
O4W	0.1939 (2)	0.11543 (16)	0.36085 (7)	0.0592 (7)
H41W	0.1629	0.1113	0.3906	0.089*
H42W	0.1458	0.0961	0.3384	0.089*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0193 (8)	0.0290 (10)	0.0280 (9)	0.0044 (7)	−0.0052 (7)	0.0038 (8)
O2	0.0161 (8)	0.0238 (8)	0.0191 (8)	−0.0027 (6)	−0.0008 (6)	0.0072 (7)
O3	0.0118 (8)	0.0276 (9)	0.0225 (8)	0.0002 (6)	−0.0002 (6)	0.0040 (7)
O4	0.0206 (9)	0.0240 (9)	0.0212 (8)	−0.0033 (7)	0.0021 (7)	0.0031 (7)
N1	0.0113 (9)	0.0221 (10)	0.0187 (9)	0.0017 (7)	0.0022 (7)	0.0036 (8)
N2	0.0198 (11)	0.0497 (14)	0.0230 (10)	0.0108 (10)	0.0054 (9)	0.0175 (10)
C1	0.0181 (11)	0.0162 (11)	0.0168 (11)	−0.0034 (8)	0.0031 (9)	−0.0009 (9)
C2	0.0189 (12)	0.0154 (11)	0.0168 (10)	−0.0028 (8)	−0.0027 (9)	−0.0006 (8)
C3	0.0127 (10)	0.0184 (11)	0.0195 (11)	−0.0006 (8)	0.0004 (9)	−0.0008 (9)
C4	0.0166 (11)	0.0231 (11)	0.0178 (10)	0.0006 (9)	0.0029 (10)	0.0036 (9)
C5	0.0184 (12)	0.0217 (12)	0.0164 (10)	0.0031 (9)	−0.0012 (9)	0.0020 (9)
C6	0.0115 (11)	0.0180 (11)	0.0195 (11)	0.0001 (8)	0.0013 (8)	−0.0015 (9)
C7	0.0127 (12)	0.0309 (14)	0.0214 (11)	0.0050 (9)	0.0024 (9)	0.0058 (10)
C8	0.0159 (11)	0.0225 (12)	0.0182 (11)	0.0039 (9)	0.0011 (9)	0.0010 (9)
C9	0.0176 (11)	0.0144 (11)	0.0237 (12)	0.0019 (9)	0.0033 (9)	−0.0041 (9)
C10	0.0155 (12)	0.0196 (12)	0.0292 (12)	−0.0004 (9)	−0.0009 (9)	0.0027 (10)
C11	0.0228 (13)	0.0196 (12)	0.0289 (12)	0.0017 (9)	−0.0084 (10)	−0.0020 (10)
C12	0.0270 (14)	0.0403 (17)	0.0307 (14)	0.0030 (11)	−0.0122 (11)	0.0006 (12)
C13	0.0330 (16)	0.0352 (14)	0.0197 (11)	0.0105 (11)	−0.0083 (11)	−0.0009 (11)
C14	0.0307 (14)	0.0329 (14)	0.0166 (11)	0.0095 (11)	−0.0032 (10)	−0.0005 (10)
C15	0.0314 (15)	0.0507 (18)	0.0193 (12)	0.0195 (13)	−0.0010 (11)	0.0071 (12)
C16	0.0188 (12)	0.0315 (14)	0.0316 (13)	0.0022 (10)	0.0019 (10)	0.0130 (11)
C17	0.0169 (12)	0.0324 (15)	0.0282 (13)	0.0002 (10)	0.0038 (10)	0.0103 (11)
C18	0.0196 (12)	0.0255 (13)	0.0216 (11)	0.0083 (10)	−0.0032 (10)	−0.0014 (10)
C19	0.0318 (14)	0.0359 (15)	0.0203 (12)	0.0141 (11)	−0.0057 (10)	−0.0067 (10)
C20	0.0357 (15)	0.0480 (18)	0.0178 (12)	0.0235 (13)	0.0014 (11)	0.0038 (12)
C21	0.0186 (13)	0.0488 (16)	0.0218 (12)	0.0160 (11)	0.0052 (10)	0.0102 (11)
C22	0.0241 (14)	0.0308 (13)	0.0188 (11)	−0.0052 (10)	−0.0004 (10)	0.0077 (10)
C23	0.0139 (12)	0.0394 (15)	0.0230 (12)	0.0022 (10)	0.0038 (10)	0.0009 (11)
S1	0.0225 (4)	0.0189 (4)	0.0162 (3)	0.000	0.0008 (3)	0.000
O5	0.0267 (17)	0.0285 (17)	0.0094 (13)	−0.0028 (15)	0.0047 (13)	−0.0015 (13)
O6	0.023 (2)	0.0222 (16)	0.0296 (18)	0.0016 (13)	0.0011 (14)	−0.0085 (13)
O7	0.0252 (19)	0.038 (2)	0.0310 (19)	−0.0047 (16)	0.0068 (16)	0.0110 (17)
O8	0.028 (2)	0.0302 (19)	0.0278 (18)	0.0052 (15)	−0.0113 (16)	−0.0021 (16)
O1W	0.056 (2)	0.0438 (17)	0.079 (2)	0.000	−0.0313 (19)	0.000
O2W	0.0373 (11)	0.0339 (11)	0.0553 (13)	−0.0071 (8)	0.0090 (10)	−0.0085 (9)
O3W	0.0433 (12)	0.0327 (11)	0.0535 (12)	−0.0011 (9)	−0.0104 (10)	−0.0090 (9)
O4W	0.0963 (18)	0.0553 (14)	0.0260 (10)	−0.0284 (13)	−0.0190 (11)	0.0048 (10)

Geometric parameters (Å, º)

O1—C11	1.431 (3)	C13—C14	1.320 (4)
O1—C12	1.445 (3)	C13—H13	0.9500
O2—C2	1.371 (2)	C14—C15	1.505 (4)
O2—C22	1.432 (3)	C14—C19	1.525 (3)
O3—C3	1.365 (3)	C15—H15A	0.9900
O3—C23	1.432 (3)	C15—H15B	0.9900
O4—C9	1.236 (3)	C16—C17	1.513 (3)
N1—C9	1.361 (3)	C16—H16A	0.9900
N1—C6	1.427 (3)	C16—H16B	0.9900
N1—C8	1.490 (3)	C17—H17A	0.9900
N2—C15	1.505 (3)	C17—H17B	0.9900
N2—C16	1.511 (3)	C18—C19	1.539 (3)
N2—C21	1.544 (3)	C18—H18	1.0000
N2—H2	0.9626	C19—C20	1.533 (4)
C1—C2	1.386 (3)	C19—H19	1.0000
C1—C6	1.389 (3)	C20—C21	1.505 (4)
C1—H1	0.9500	C20—H20A	0.9900
C2—C3	1.411 (3)	C20—H20B	0.9900
C3—C4	1.387 (3)	C21—H21	1.0000
C4—C5	1.391 (3)	C22—H22A	0.9800
C4—H4	0.9500	C22—H22B	0.9800
C5—C6	1.386 (3)	C22—H22C	0.9800
C5—C7	1.507 (3)	C23—H23A	0.9800
C7—C17	1.534 (4)	C23—H23B	0.9800
C7—C21	1.544 (3)	C23—H23C	0.9800
C7—C8	1.556 (3)	S1—O5	1.449 (3)
C8—C18	1.524 (3)	S1—O7	1.453 (3)
C8—H8	1.0000	S1—O8	1.511 (3)
C9—C10	1.508 (3)	S1—O6	1.514 (3)
C10—C11	1.551 (3)	O1W—H11W	0.8836
C10—H10A	0.9900	O2W—H21W	0.8807
C10—H10B	0.9900	O2W—H22W	0.8798
C11—C18	1.531 (3)	O3W—H31W	0.8812
C11—H11	1.0000	O3W—H32W	0.8803
C12—C13	1.493 (4)	O4W—H41W	0.8806
C12—H12A	0.9900	O4W—H42W	0.8803
C12—H12B	0.9900
C11—O1—C12	115.47 (18)	C16—C17—H17B	111.1
C2—O2—C22	116.00 (16)	C7—C17—H17B	111.1
C3—O3—C23	116.17 (17)	H17A—C17—H17B	109.0
C9—N1—C6	125.77 (18)	C8—C18—C11	107.86 (18)
C9—N1—C8	119.28 (18)	C8—C18—C19	112.7 (2)
C6—N1—C8	109.44 (17)	C11—C18—C19	117.94 (19)
C15—N2—C16	112.79 (19)	C8—C18—H18	105.8
C15—N2—C21	113.9 (2)	C11—C18—H18	105.8
C16—N2—C21	107.52 (17)	C19—C18—H18	105.8
C15—N2—H2	108.2	C14—C19—C20	108.9 (2)
C16—N2—H2	108.0	C14—C19—C18	114.0 (2)
C21—N2—H2	106.0	C20—C19—C18	106.8 (2)
C2—C1—C6	117.35 (19)	C14—C19—H19	109.0
C2—C1—H1	121.3	C20—C19—H19	109.0
C6—C1—H1	121.3	C18—C19—H19	109.0
O2—C2—C1	123.38 (19)	C21—C20—C19	109.2 (2)
O2—C2—C3	115.42 (18)	C21—C20—H20A	109.8
C1—C2—C3	121.19 (19)	C19—C20—H20A	109.8
O3—C3—C4	124.3 (2)	C21—C20—H20B	109.8
O3—C3—C2	115.72 (18)	C19—C20—H20B	109.8
C4—C3—C2	120.01 (19)	H20A—C20—H20B	108.3
C3—C4—C5	118.9 (2)	C20—C21—C7	116.0 (2)
C3—C4—H4	120.5	C20—C21—N2	110.0 (2)
C5—C4—H4	120.5	C7—C21—N2	104.09 (19)
C6—C5—C4	120.0 (2)	C20—C21—H21	108.8
C6—C5—C7	110.86 (19)	C7—C21—H21	108.8
C4—C5—C7	129.0 (2)	N2—C21—H21	108.8
C5—C6—C1	122.29 (19)	O2—C22—H22A	109.5
C5—C6—N1	109.30 (18)	O2—C22—H22B	109.5
C1—C6—N1	128.39 (19)	H22A—C22—H22B	109.5
C5—C7—C17	112.5 (2)	O2—C22—H22C	109.5
C5—C7—C21	114.94 (19)	H22A—C22—H22C	109.5
C17—C7—C21	101.66 (19)	H22B—C22—H22C	109.5
C5—C7—C8	102.26 (17)	O3—C23—H23A	109.5
C17—C7—C8	111.62 (19)	O3—C23—H23B	109.5
C21—C7—C8	114.3 (2)	H23A—C23—H23B	109.5
N1—C8—C18	106.56 (18)	O3—C23—H23C	109.5
N1—C8—C7	104.27 (17)	H23A—C23—H23C	109.5
C18—C8—C7	116.53 (19)	H23B—C23—H23C	109.5
N1—C8—H8	109.7	O5^i—S1—O5	176.5 (3)
C18—C8—H8	109.7	O5^i—S1—O7	64.5 (2)
C7—C8—H8	109.7	O5—S1—O7	113.4 (2)
O4—C9—N1	123.0 (2)	O5—S1—O7^i	64.5 (2)
O4—C9—C10	121.6 (2)	O7—S1—O7^i	111.6 (3)
N1—C9—C10	115.33 (19)	O5^i—S1—O8	70.75 (19)
C9—C10—C11	118.04 (18)	O5—S1—O8	108.21 (19)
C9—C10—H10A	107.8	O7—S1—O8	110.82 (19)
C11—C10—H10A	107.8	O7^i—S1—O8	47.71 (17)
C9—C10—H10B	107.8	O5^i—S1—O8^i	108.21 (19)
C11—C10—H10B	107.8	O5—S1—O8^i	70.75 (19)
H10A—C10—H10B	107.1	O7—S1—O8^i	47.71 (17)
O1—C11—C18	114.52 (19)	O7^i—S1—O8^i	110.82 (19)
O1—C11—C10	103.61 (18)	O8—S1—O8^i	147.2 (3)
C18—C11—C10	110.35 (18)	O5^i—S1—O6	74.14 (17)
O1—C11—H11	109.4	O5—S1—O6	109.32 (18)
C18—C11—H11	109.4	O7—S1—O6	107.94 (19)
C10—C11—H11	109.4	O7^i—S1—O6	138.86 (19)
O1—C12—C13	110.7 (2)	O8—S1—O6	107.00 (18)
O1—C12—H12A	109.5	O8^i—S1—O6	103.90 (18)
C13—C12—H12A	109.5	O5^i—S1—O6^i	109.32 (18)
O1—C12—H12B	109.5	O5—S1—O6^i	74.14 (17)
C13—C12—H12B	109.5	O7—S1—O6^i	138.86 (19)
H12A—C12—H12B	108.1	O7^i—S1—O6^i	107.94 (19)
C14—C13—C12	121.9 (2)	O8—S1—O6^i	103.90 (18)
C14—C13—H13	119.0	O8^i—S1—O6^i	107.00 (18)
C12—C13—H13	119.0	S1—O5—O7^i	57.88 (16)
C13—C14—C15	121.8 (2)	S1—O5—O8^i	56.30 (15)
C13—C14—C19	122.4 (2)	O7^i—O5—O8^i	96.7 (2)
C15—C14—C19	115.9 (2)	S1—O5—O6^i	54.58 (14)
C14—C15—N2	110.24 (19)	O7^i—O5—O6^i	91.7 (2)
C14—C15—H15A	109.6	O8^i—O5—O6^i	87.9 (2)
N2—C15—H15A	109.6	O6^i—O6—S1	70.64 (12)
C14—C15—H15B	109.6	O6^i—O6—O5^i	117.3 (2)
N2—C15—H15B	109.6	S1—O6—O5^i	51.29 (13)
H15A—C15—H15B	108.1	O8^i—O7—S1	68.7 (2)
N2—C16—C17	104.38 (19)	O8^i—O7—O5^i	121.0 (3)
N2—C16—H16A	110.9	S1—O7—O5^i	57.64 (17)
C17—C16—H16A	110.9	O7^i—O8—S1	63.6 (2)
N2—C16—H16B	110.9	O7^i—O8—O5^i	111.4 (3)
C17—C16—H16B	110.9	S1—O8—O5^i	52.94 (15)
H16A—C16—H16B	108.9	H21W—O2W—H22W	107.2
C16—C17—C7	103.5 (2)	H31W—O3W—H32W	107.1
C16—C17—H17A	111.1	H41W—O4W—H42W	107.8
C7—C17—H17A	111.1
C22—O2—C2—C1	−2.3 (3)	C15—C14—C19—C20	−0.9 (3)
C22—O2—C2—C3	177.35 (19)	C13—C14—C19—C18	61.2 (3)
C6—C1—C2—O2	−178.68 (19)	C15—C14—C19—C18	−120.1 (2)
C6—C1—C2—C3	1.7 (3)	C8—C18—C19—C14	59.3 (3)
C23—O3—C3—C4	10.6 (3)	C11—C18—C19—C14	−67.4 (3)
C23—O3—C3—C2	−170.38 (19)	C8—C18—C19—C20	−61.0 (3)
O2—C2—C3—O3	−3.6 (3)	C11—C18—C19—C20	172.2 (2)
C1—C2—C3—O3	176.00 (19)	C14—C19—C20—C21	−56.6 (3)
O2—C2—C3—C4	175.40 (19)	C18—C19—C20—C21	67.0 (3)
C1—C2—C3—C4	−5.0 (3)	C19—C20—C21—C7	−54.9 (3)
O3—C3—C4—C5	−177.1 (2)	C19—C20—C21—N2	62.8 (2)
C2—C3—C4—C5	4.0 (3)	C5—C7—C21—C20	−84.1 (3)
C3—C4—C5—C6	0.1 (3)	C17—C7—C21—C20	154.2 (2)
C3—C4—C5—C7	−174.9 (2)	C8—C7—C21—C20	33.8 (3)
C4—C5—C6—C1	−3.4 (3)	C5—C7—C21—N2	155.0 (2)
C7—C5—C6—C1	172.4 (2)	C17—C7—C21—N2	33.2 (2)
C4—C5—C6—N1	175.0 (2)	C8—C7—C21—N2	−87.2 (2)
C7—C5—C6—N1	−9.2 (3)	C15—N2—C21—C20	−10.3 (3)
C2—C1—C6—C5	2.4 (3)	C16—N2—C21—C20	−136.0 (2)
C2—C1—C6—N1	−175.6 (2)	C15—N2—C21—C7	114.6 (2)
C9—N1—C6—C5	−157.5 (2)	C16—N2—C21—C7	−11.1 (3)
C8—N1—C6—C5	−4.2 (2)	O7—S1—O5—O7^i	−103.7 (3)
C9—N1—C6—C1	20.8 (4)	O8—S1—O5—O7^i	19.6 (2)
C8—N1—C6—C1	174.1 (2)	O8^i—S1—O5—O7^i	−125.7 (2)
C6—C5—C7—C17	−102.1 (2)	O6—S1—O5—O7^i	135.8 (2)
C4—C5—C7—C17	73.2 (3)	O6^i—S1—O5—O7^i	119.4 (2)
C6—C5—C7—C21	142.2 (2)	O7—S1—O5—O8^i	22.0 (2)
C4—C5—C7—C21	−42.5 (4)	O7^i—S1—O5—O8^i	125.7 (2)
C6—C5—C7—C8	17.8 (2)	O8—S1—O5—O8^i	145.3 (3)
C4—C5—C7—C8	−166.9 (2)	O6—S1—O5—O8^i	−98.5 (2)
C9—N1—C8—C18	46.4 (2)	O6^i—S1—O5—O8^i	−114.9 (2)
C6—N1—C8—C18	−108.9 (2)	O7—S1—O5—O6^i	136.9 (2)
C9—N1—C8—C7	170.26 (19)	O7^i—S1—O5—O6^i	−119.4 (2)
C6—N1—C8—C7	15.0 (2)	O8—S1—O5—O6^i	−99.8 (2)
C5—C7—C8—N1	−19.0 (2)	O8^i—S1—O5—O6^i	114.9 (2)
C17—C7—C8—N1	101.5 (2)	O6—S1—O5—O6^i	16.4 (3)
C21—C7—C8—N1	−143.85 (19)	O5^i—S1—O6—O6^i	154.7 (4)
C5—C7—C8—C18	98.1 (2)	O5—S1—O6—O6^i	−25.8 (4)
C17—C7—C8—C18	−141.4 (2)	O7—S1—O6—O6^i	−149.5 (4)
C21—C7—C8—C18	−26.7 (3)	O7^i—S1—O6—O6^i	47.2 (5)
C6—N1—C9—O4	−24.7 (3)	O8—S1—O6—O6^i	91.2 (4)
C8—N1—C9—O4	−175.6 (2)	O8^i—S1—O6—O6^i	−99.9 (4)
C6—N1—C9—C10	157.1 (2)	O5—S1—O6—O5^i	179.48 (4)
C8—N1—C9—C10	6.2 (3)	O7—S1—O6—O5^i	55.8 (2)
O4—C9—C10—C11	145.4 (2)	O7^i—S1—O6—O5^i	−107.5 (3)
N1—C9—C10—C11	−36.4 (3)	O8—S1—O6—O5^i	−63.6 (2)
C12—O1—C11—C18	−66.2 (3)	O8^i—S1—O6—O5^i	105.3 (2)
C12—O1—C11—C10	173.60 (19)	O6^i—S1—O6—O5^i	−154.7 (4)
C9—C10—C11—O1	132.9 (2)	O5^i—S1—O7—O8^i	154.5 (3)
C9—C10—C11—C18	9.9 (3)	O5—S1—O7—O8^i	−28.6 (3)
C11—O1—C12—C13	88.8 (2)	O7^i—S1—O7—O8^i	−99.0 (3)
O1—C12—C13—C14	−65.1 (3)	O8—S1—O7—O8^i	−150.5 (3)
C12—C13—C14—C15	177.8 (2)	O6—S1—O7—O8^i	92.7 (3)
C12—C13—C14—C19	−3.5 (4)	O6^i—S1—O7—O8^i	63.8 (4)
C13—C14—C15—N2	−129.5 (2)	O5—S1—O7—O5^i	177.0 (2)
C19—C14—C15—N2	51.7 (3)	O7^i—S1—O7—O5^i	106.5 (2)
C16—N2—C15—C14	77.8 (3)	O8—S1—O7—O5^i	55.1 (2)
C21—N2—C15—C14	−45.1 (3)	O8^i—S1—O7—O5^i	−154.5 (3)
C15—N2—C16—C17	−142.3 (2)	O6—S1—O7—O5^i	−61.8 (2)
C21—N2—C16—C17	−15.9 (2)	O6^i—S1—O7—O5^i	−90.6 (3)
N2—C16—C17—C7	37.1 (2)	O5^i—S1—O8—O7^i	152.3 (3)
C5—C7—C17—C16	−167.22 (18)	O5—S1—O8—O7^i	−24.2 (3)
C21—C7—C17—C16	−43.8 (2)	O7—S1—O8—O7^i	100.7 (4)
C8—C7—C17—C16	78.5 (2)	O8^i—S1—O8—O7^i	58.3 (2)
N1—C8—C18—C11	−70.5 (2)	O6—S1—O8—O7^i	−141.9 (3)
C7—C8—C18—C11	173.67 (18)	O6^i—S1—O8—O7^i	−101.8 (3)
N1—C8—C18—C19	157.55 (18)	O5—S1—O8—O5^i	−176.5 (3)
C7—C8—C18—C19	41.7 (3)	O7—S1—O8—O5^i	−51.6 (2)
O1—C11—C18—C8	−74.8 (2)	O7^i—S1—O8—O5^i	−152.3 (3)
C10—C11—C18—C8	41.6 (2)	O8^i—S1—O8—O5^i	−93.96 (15)
O1—C11—C18—C19	54.3 (3)	O6—S1—O8—O5^i	65.83 (19)
C10—C11—C18—C19	170.7 (2)	O6^i—S1—O8—O5^i	105.94 (19)
C13—C14—C19—C20	−179.6 (2)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O6^i	0.96	1.83	2.712 (4)	151
N2—H2···O5	0.96	2.00	2.873 (4)	150
N2—H2···O7^i	0.96	2.36	3.141 (4)	138
O1W—H11W···O3W	0.88	2.04	2.834 (2)	150
O2W—H21W···O4W	0.88	1.88	2.756 (3)	175
O2W—H22W···O6	0.88	1.91	2.716 (4)	151
O2W—H22W···O6^i	0.88	2.17	2.976 (4)	152
O3W—H31W···O2W	0.88	1.89	2.748 (3)	165
O3W—H32W···O7^ii	0.88	1.97	2.769 (4)	150
O3W—H32W···O8^iii	0.88	2.27	3.093 (4)	155
O4W—H41W···O4^iv	0.88	1.95	2.808 (3)	164
O4W—H42W···O8	0.88	2.00	2.801 (4)	151
O4W—H42W···O5^i	0.88	2.14	2.983 (4)	160

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