2,3-Dimeth­oxy-10-oxostrychnidinium 3-carboxy­benzoate trihydrate: the 1:1 proton-transfer compound of brucine with isophthalic acid

The structure of the title, compound C₂₃H₂₇N₂O₄⁺·C₈H₅O₄⁻·3H₂O, has been determined at 130 K. The hydrogen isophthalate anions and the water mol­ecules (one of which is disordered over two approximately equal sites) associate through extensive hydrogen-bonded inter­actions, including those with the common undulating brucinium cation layer substructures, forming a three-dimensional framework structure.

Key indicators

• Single-crystal X-ray study
• T = 130 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in solvent or counterion
• R factor = 0.054
• wR factor = 0.095
• Data-to-parameter ratio = 9.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H11W   ..  H321    ..       2.06 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D       H22W   ..  H32W    ..       2.03 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D       H22W   ..  H34W    ..       2.09 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  C211   ..  C211    ..       3.09 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.68 Ratio
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      25.00 Perc.
PLAT415_ALERT_2_C Short Inter D-H..H-X       H20B   ..  H22W    ..       2.12 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

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           27.48
           From the CIF: _reflns_number_total               3815
           Count of symmetry unique reflns         3815
           Completeness (_total/calc)            100.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
   5 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
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997) in WinGX (Farrugia, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) in WinGX; molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

2,3-dimethoxy-10-oxostrychnidinium 3-carboxybenzoate trihydrate

Crystal data

C23H27N2O4^+·C8H5O4^−·3H2O	Dx = 1.395 Mg m^−3
Mr = 614.63	Melting point = 454.6–457.6 K
Orthorhombic, P21212	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 2302 reflections
a = 12.4560 (9) Å	θ = 2.6–21.4°
b = 29.3559 (19) Å	µ = 0.11 mm^−1
c = 8.0020 (5) Å	T = 130 K
V = 2926.0 (3) Å^3	Prismatic, colourless
Z = 4	0.48 × 0.17 × 0.11 mm
F(000) = 1304

Data collection

Bruker Model CCD area-detector diffractometer	2474 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.098
Graphite monochromator	θmax = 27.5°, θmin = 1.8°
φ and ω scans	h = −15→16
18440 measured reflections	k = −35→37
3815 independent reflections	l = −7→10

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 0.85	w = 1/[σ^2(Fo^2) + (0.0105P)^2] where P = (Fo^2 + 2Fc^2)/3
3815 reflections	(Δ/σ)max = 0.006
410 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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)
O2	0.47613 (15)	0.77114 (6)	0.8091 (3)	0.0247 (7)
O3	0.36765 (15)	0.84513 (6)	0.8584 (3)	0.0237 (7)
O24	−0.22072 (15)	0.68994 (6)	0.7313 (3)	0.0276 (7)
O25	−0.03119 (17)	0.82700 (6)	0.7690 (3)	0.0306 (7)
N9	0.0335 (2)	0.75550 (7)	0.8097 (3)	0.0200 (8)
N19	0.11324 (19)	0.60176 (7)	0.7499 (3)	0.0213 (8)
C1	0.3133 (2)	0.72514 (9)	0.7920 (4)	0.0197 (9)
C2	0.3663 (2)	0.76619 (9)	0.8105 (4)	0.0193 (9)
C3	0.3070 (2)	0.80646 (9)	0.8353 (4)	0.0202 (9)
C4	0.1956 (2)	0.80605 (9)	0.8335 (4)	0.0218 (10)
C5	0.1454 (2)	0.76422 (9)	0.8101 (4)	0.0187 (9)
C6	0.2018 (2)	0.72453 (9)	0.7920 (4)	0.0198 (9)
C7	0.1289 (2)	0.68403 (8)	0.7975 (4)	0.0197 (9)
C8	0.0151 (2)	0.70575 (8)	0.7804 (4)	0.0183 (9)
C10	−0.0460 (2)	0.78527 (10)	0.7705 (4)	0.0240 (10)
C11	−0.1549 (2)	0.76490 (9)	0.7334 (4)	0.0280 (10)
C12	−0.1554 (2)	0.71983 (9)	0.6356 (4)	0.0228 (9)
C13	−0.0404 (2)	0.70268 (8)	0.6102 (4)	0.0186 (9)
C14	−0.0225 (2)	0.65689 (9)	0.5252 (4)	0.0219 (9)
C15	0.0992 (2)	0.65227 (10)	0.4996 (4)	0.0236 (10)
C16	0.1523 (2)	0.64611 (8)	0.6686 (4)	0.0200 (9)
C17	0.1413 (2)	0.65774 (9)	0.9626 (4)	0.0225 (10)
C18	0.0870 (2)	0.61258 (9)	0.9290 (4)	0.0234 (10)
C20	0.0184 (2)	0.58062 (8)	0.6604 (4)	0.0246 (10)
C21	−0.0639 (2)	0.61590 (9)	0.6226 (4)	0.0230 (10)
C22	−0.1638 (2)	0.61203 (10)	0.6747 (4)	0.0287 (10)
C23	−0.2486 (2)	0.64796 (9)	0.6502 (4)	0.0343 (11)
C26	0.5377 (2)	0.73012 (9)	0.7844 (4)	0.0283 (10)
C27	0.3109 (3)	0.88789 (8)	0.8610 (5)	0.0363 (11)
O111	0.24779 (17)	1.03436 (6)	0.2520 (3)	0.0287 (7)
O121	0.24696 (17)	1.04780 (6)	0.5241 (3)	0.0307 (7)
O311	−0.09600 (18)	0.87597 (6)	0.1842 (3)	0.0372 (8)
O321	−0.03598 (18)	0.93398 (6)	0.0288 (3)	0.0325 (8)
C31	0.0249 (2)	0.92875 (9)	0.3078 (4)	0.0231 (10)
C41	0.0121 (2)	0.90960 (9)	0.4666 (4)	0.0274 (11)
C51	0.0657 (2)	0.92810 (10)	0.6025 (4)	0.0305 (11)
C61	0.1311 (2)	0.96599 (10)	0.5814 (4)	0.0275 (10)
C111	0.1476 (2)	0.98419 (9)	0.4227 (4)	0.0228 (10)
C121	0.2184 (2)	1.02511 (9)	0.3997 (4)	0.0239 (10)
C211	0.0935 (2)	0.96539 (8)	0.2872 (4)	0.0214 (9)
C321	−0.0422 (2)	0.91037 (9)	0.1684 (4)	0.0260 (10)
O1W	0.8285 (2)	0.90173 (8)	0.8034 (3)	0.0322 (8)
O2W	0.1094 (3)	0.48785 (8)	0.9534 (4)	0.0526 (10)
O3WB	0.4056 (7)	1.0247 (6)	0.7312 (11)	0.061 (4)	0.43 (2)
O3WA	0.3926 (5)	0.9942 (5)	0.7094 (8)	0.063 (3)	0.57 (2)
H1	0.35270	0.69760	0.77950	0.0240*
H4	0.15530	0.83320	0.84770	0.0260*
H8	−0.03330	0.69330	0.86900	0.0220*
H11A	−0.19710	0.7875	0.66930	0.0340*
H11B	−0.19250	0.75990	0.84080	0.0340*
H12	−0.18960	0.72490	0.52410	0.0270*
H13	−0.00440	0.72580	0.53760	0.0220*
H14	−0.05820	0.65740	0.41320	0.0260*
H15A	0.11480	0.62570	0.42740	0.0280*
H15B	0.12770	0.67990	0.44420	0.0280*
H16	0.23170	0.64410	0.65190	0.0240*
H17A	0.21810	0.65330	0.99060	0.0270*
H17B	0.10580	0.67410	1.05570	0.0270*
H18A	0.11510	0.58870	1.00450	0.0280*
H18B	0.00840	0.61510	0.94520	0.0280*
H19	0.161 (3)	0.5787 (11)	0.740 (5)	0.081 (12)*
H20A	0.04300	0.56630	0.55510	0.0290*
H20B	−0.01360	0.55660	0.73150	0.0290*
H22	−0.18360	0.58490	0.73130	0.0340*
H23A	−0.25830	0.65360	0.52910	0.0410*
H23B	−0.31770	0.63680	0.69550	0.0410*
H26A	0.51730	0.70750	0.86870	0.0430*
H26B	0.61440	0.73700	0.79510	0.0430*
H26C	0.52340	0.71790	0.67260	0.0430*
H27A	0.26830	0.89100	0.75860	0.0550*
H27B	0.36250	0.91300	0.86790	0.0550*
H27C	0.26310	0.88880	0.95830	0.0550*
H41	−0.03330	0.88390	0.48150	0.0330*
H51	0.05780	0.91480	0.71000	0.0370*
H61	0.16460	0.97960	0.67570	0.0330*
H211	0.10370	0.97790	0.17890	0.0260*
H321	−0.082 (5)	0.923 (2)	−0.051 (6)	0.076 (12)*
H31W	0.344 (5)	1.011 (2)	0.650 (9)	0.10 (2)*	0.570
H32W	0.373 (5)	0.991 (2)	0.817 (9)	0.11 (2)*	0.570
H33W	0.353 (5)	1.033 (2)	0.661 (9)	0.11 (3)*	0.430
H34W	0.401 (5)	1.013 (2)	0.834 (9)	0.11 (3)*	0.430
H11W	0.867 (2)	0.8773 (9)	0.770 (4)	0.037 (10)*
H12W	0.805 (3)	0.9175 (10)	0.715 (4)	0.045 (13)*
H21W	0.164 (4)	0.4830 (15)	0.892 (6)	0.093 (15)*
H22W	0.054 (7)	0.470 (4)	0.970 (10)	0.093 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0179 (11)	0.0212 (10)	0.0349 (13)	0.0012 (9)	−0.0008 (10)	−0.0010 (10)
O3	0.0249 (12)	0.0170 (10)	0.0293 (13)	0.0012 (9)	−0.0017 (10)	−0.0024 (10)
O24	0.0194 (11)	0.0267 (10)	0.0368 (14)	−0.0020 (9)	0.0025 (11)	0.0012 (11)
O25	0.0272 (12)	0.0158 (10)	0.0487 (15)	0.0024 (9)	−0.0039 (12)	0.0024 (10)
N9	0.0186 (13)	0.0165 (11)	0.0248 (15)	0.0016 (10)	0.0020 (12)	−0.0008 (11)
N19	0.0210 (14)	0.0184 (12)	0.0245 (14)	−0.0012 (11)	−0.0023 (12)	−0.0002 (11)
C1	0.0199 (16)	0.0150 (14)	0.0242 (17)	0.0059 (12)	0.0001 (14)	0.0022 (14)
C2	0.0181 (16)	0.0246 (15)	0.0153 (16)	0.0024 (13)	−0.0010 (13)	0.0004 (14)
C3	0.0275 (18)	0.0163 (14)	0.0168 (17)	0.0001 (13)	−0.0022 (14)	0.0001 (14)
C4	0.0226 (18)	0.0164 (14)	0.0264 (19)	0.0053 (13)	0.0000 (15)	0.0034 (14)
C5	0.0137 (15)	0.0246 (15)	0.0177 (16)	0.0019 (13)	−0.0023 (13)	0.0043 (14)
C6	0.0191 (16)	0.0200 (14)	0.0203 (17)	0.0005 (12)	−0.0026 (14)	−0.0011 (14)
C7	0.0172 (16)	0.0194 (14)	0.0224 (17)	0.0002 (12)	−0.0015 (14)	0.0004 (14)
C8	0.0169 (16)	0.0178 (14)	0.0202 (17)	−0.0024 (11)	0.0014 (13)	0.0031 (13)
C10	0.0210 (17)	0.0335 (17)	0.0175 (17)	0.0049 (14)	0.0028 (14)	0.0033 (14)
C11	0.0201 (17)	0.0290 (16)	0.035 (2)	0.0052 (14)	−0.0005 (16)	−0.0010 (16)
C12	0.0185 (16)	0.0230 (15)	0.0270 (18)	0.0008 (13)	−0.0049 (14)	0.0061 (14)
C13	0.0198 (16)	0.0164 (15)	0.0196 (16)	−0.0050 (13)	−0.0001 (14)	0.0053 (13)
C14	0.0182 (17)	0.0281 (16)	0.0193 (16)	−0.0001 (14)	−0.0043 (14)	0.0021 (14)
C15	0.0285 (18)	0.0210 (16)	0.0213 (18)	−0.0005 (14)	0.0046 (15)	0.0028 (14)
C16	0.0184 (16)	0.0156 (14)	0.0261 (18)	−0.0022 (12)	0.0021 (14)	0.0006 (14)
C17	0.0249 (18)	0.0203 (16)	0.0223 (17)	0.0045 (14)	0.0001 (14)	0.0008 (14)
C18	0.0269 (18)	0.0215 (16)	0.0217 (18)	0.0032 (14)	0.0044 (14)	0.0047 (14)
C20	0.0260 (18)	0.0193 (14)	0.0284 (18)	−0.0055 (13)	0.0034 (16)	−0.0011 (14)
C21	0.0239 (18)	0.0189 (15)	0.0262 (18)	−0.0010 (13)	−0.0079 (15)	−0.0050 (14)
C22	0.0247 (18)	0.0263 (16)	0.035 (2)	−0.0099 (14)	−0.0053 (16)	−0.0020 (16)
C23	0.0220 (18)	0.0330 (17)	0.048 (2)	−0.0078 (16)	−0.0043 (18)	0.0026 (17)
C26	0.0204 (17)	0.0286 (16)	0.036 (2)	0.0069 (14)	−0.0010 (16)	0.0017 (16)
C27	0.042 (2)	0.0130 (15)	0.054 (2)	0.0019 (15)	−0.0128 (19)	−0.0046 (17)
O111	0.0335 (13)	0.0240 (10)	0.0285 (13)	−0.0130 (10)	0.0006 (12)	0.0023 (10)
O121	0.0262 (13)	0.0319 (12)	0.0341 (13)	−0.0026 (10)	−0.0020 (12)	−0.0081 (11)
O311	0.0428 (14)	0.0213 (10)	0.0476 (15)	−0.0117 (10)	−0.0024 (13)	0.0015 (11)
O321	0.0387 (14)	0.0289 (12)	0.0299 (13)	−0.0094 (11)	0.0035 (12)	0.0043 (11)
C31	0.0179 (16)	0.0186 (14)	0.0328 (19)	0.0022 (13)	0.0033 (15)	0.0035 (14)
C41	0.0211 (19)	0.0200 (16)	0.041 (2)	0.0016 (13)	0.0051 (16)	0.0088 (16)
C51	0.0271 (19)	0.0334 (18)	0.031 (2)	0.0025 (15)	0.0017 (16)	0.0125 (16)
C61	0.0234 (18)	0.0331 (17)	0.0261 (19)	0.0030 (15)	0.0003 (15)	0.0000 (15)
C111	0.0201 (18)	0.0168 (15)	0.0314 (19)	0.0056 (13)	0.0025 (15)	0.0027 (14)
C121	0.0186 (17)	0.0201 (16)	0.033 (2)	0.0019 (13)	−0.0011 (15)	−0.0023 (15)
C211	0.0185 (16)	0.0195 (14)	0.0262 (18)	0.0026 (13)	0.0024 (15)	0.0018 (14)
C321	0.0201 (17)	0.0220 (16)	0.036 (2)	0.0044 (14)	0.0071 (16)	−0.0047 (16)
O1W	0.0331 (14)	0.0315 (13)	0.0319 (15)	0.0041 (11)	0.0016 (12)	0.0055 (13)
O2W	0.063 (2)	0.0312 (14)	0.0635 (19)	−0.0076 (15)	−0.0202 (17)	0.0021 (14)
O3WB	0.070 (5)	0.058 (10)	0.057 (5)	0.017 (5)	−0.001 (4)	0.011 (5)
O3WA	0.059 (4)	0.055 (7)	0.075 (4)	0.010 (3)	−0.022 (3)	0.003 (4)

Geometric parameters (Å, º)

O2—C2	1.376 (3)	C15—C16	1.516 (4)
O2—C26	1.441 (3)	C17—C18	1.512 (4)
O3—C3	1.376 (3)	C20—C21	1.488 (4)
O3—C27	1.441 (3)	C21—C22	1.317 (4)
O24—C12	1.421 (3)	C22—C23	1.506 (4)
O24—C23	1.435 (3)	C1—H1	0.9500
O25—C10	1.239 (3)	C4—H4	0.9500
O111—C121	1.267 (4)	C8—H8	1.0000
O121—C121	1.250 (4)	C11—H11B	0.9900
O3WA—H31W	0.91 (6)	C11—H11A	0.9900
O3WA—H32W	0.90 (7)	C12—H12	1.0000
O3WB—H33W	0.90 (7)	C13—H13	1.0000
O3WB—H34W	0.89 (6)	C14—H14	1.0000
O311—C321	1.219 (3)	C15—H15B	0.9900
O321—C321	1.317 (4)	C15—H15A	0.9900
O321—H321	0.92 (5)	C16—H16	1.0000
O1W—H11W	0.90 (3)	C17—H17A	0.9900
O1W—H12W	0.90 (3)	C17—H17B	0.9900
O2W—H21W	0.85 (5)	C18—H18B	0.9900
O2W—H22W	0.85 (9)	C18—H18A	0.9900
N9—C5	1.417 (4)	C20—H20A	0.9900
N9—C8	1.497 (3)	C20—H20B	0.9900
N9—C10	1.358 (4)	C22—H22	0.9500
N19—C16	1.535 (3)	C23—H23A	0.9900
N19—C20	1.515 (4)	C23—H23B	0.9900
N19—C18	1.504 (4)	C26—H26B	0.9800
N19—H19	0.91 (3)	C26—H26A	0.9800
C1—C6	1.389 (4)	C26—H26C	0.9800
C1—C2	1.382 (4)	C27—H27C	0.9800
C2—C3	1.408 (4)	C27—H27A	0.9800
C3—C4	1.388 (4)	C27—H27B	0.9800
C4—C5	1.391 (4)	C31—C211	1.384 (4)
C5—C6	1.368 (4)	C31—C321	1.495 (4)
C6—C7	1.497 (4)	C31—C41	1.399 (4)
C7—C17	1.538 (4)	C41—C51	1.387 (4)
C7—C16	1.545 (4)	C51—C61	1.389 (4)
C7—C8	1.560 (4)	C61—C111	1.393 (4)
C8—C13	1.530 (4)	C111—C211	1.391 (4)
C10—C11	1.512 (4)	C111—C121	1.502 (4)
C11—C12	1.537 (4)	C41—H41	0.9500
C12—C13	1.532 (4)	C51—H51	0.9500
C13—C14	1.523 (4)	C61—H61	0.9500
C14—C21	1.524 (4)	C211—H211	0.9500
C14—C15	1.536 (4)
C2—O2—C26	116.23 (19)	H11A—C11—H11B	107.00
C3—O3—C27	116.8 (2)	O24—C12—H12	109.00
C12—O24—C23	115.2 (2)	C13—C12—H12	109.00
H31W—O3WA—H32W	112 (7)	C11—C12—H12	109.00
H33W—O3WB—H34W	129 (6)	C14—C13—H13	106.00
C321—O321—H321	112 (4)	C8—C13—H13	106.00
H11W—O1W—H12W	111 (3)	C12—C13—H13	106.00
H21W—O2W—H22W	127 (8)	C15—C14—H14	109.00
C5—N9—C10	127.0 (2)	C21—C14—H14	109.00
C5—N9—C8	109.1 (2)	C13—C14—H14	109.00
C8—N9—C10	118.7 (2)	C16—C15—H15A	110.00
C16—N19—C18	107.1 (2)	C14—C15—H15A	110.00
C18—N19—C20	111.6 (2)	C14—C15—H15B	110.00
C16—N19—C20	113.2 (2)	C16—C15—H15B	110.00
C16—N19—H19	113 (2)	H15A—C15—H15B	108.00
C20—N19—H19	100 (2)	C7—C16—H16	109.00
C18—N19—H19	113 (3)	C15—C16—H16	109.00
C2—C1—C6	119.3 (2)	N19—C16—H16	109.00
O2—C2—C1	124.5 (2)	C18—C17—H17A	111.00
O2—C2—C3	115.7 (2)	C18—C17—H17B	111.00
C1—C2—C3	119.8 (2)	H17A—C17—H17B	109.00
C2—C3—C4	121.1 (2)	C7—C17—H17B	111.00
O3—C3—C2	115.1 (2)	C7—C17—H17A	111.00
O3—C3—C4	123.9 (2)	C17—C18—H18A	111.00
C3—C4—C5	117.3 (2)	N19—C18—H18A	111.00
C4—C5—C6	122.4 (2)	N19—C18—H18B	111.00
N9—C5—C4	127.0 (2)	C17—C18—H18B	111.00
N9—C5—C6	110.6 (2)	H18A—C18—H18B	109.00
C1—C6—C7	128.1 (2)	N19—C20—H20B	110.00
C1—C6—C5	120.2 (2)	N19—C20—H20A	110.00
C5—C6—C7	111.2 (2)	C21—C20—H20B	110.00
C6—C7—C8	102.94 (19)	C21—C20—H20A	110.00
C16—C7—C17	101.1 (2)	H20A—C20—H20B	108.00
C6—C7—C17	111.3 (2)	C21—C22—H22	118.00
C8—C7—C16	114.0 (2)	C23—C22—H22	118.00
C8—C7—C17	111.8 (2)	C22—C23—H23B	109.00
C6—C7—C16	116.0 (2)	O24—C23—H23B	109.00
C7—C8—C13	117.7 (2)	O24—C23—H23A	109.00
N9—C8—C7	104.2 (2)	C22—C23—H23A	109.00
N9—C8—C13	105.4 (2)	H23A—C23—H23B	108.00
O25—C10—C11	121.5 (2)	H26B—C26—H26C	109.00
O25—C10—N9	122.0 (2)	H26A—C26—H26C	109.00
N9—C10—C11	116.4 (2)	O2—C26—H26B	110.00
C10—C11—C12	116.4 (2)	O2—C26—H26C	110.00
O24—C12—C11	105.0 (2)	O2—C26—H26A	109.00
C11—C12—C13	110.3 (2)	H26A—C26—H26B	109.00
O24—C12—C13	113.8 (2)	H27B—C27—H27C	109.00
C8—C13—C12	106.6 (2)	H27A—C27—H27C	109.00
C12—C13—C14	119.1 (2)	O3—C27—H27C	109.00
C8—C13—C14	112.5 (2)	O3—C27—H27A	110.00
C13—C14—C15	106.4 (2)	O3—C27—H27B	110.00
C15—C14—C21	109.4 (2)	H27A—C27—H27B	109.00
C13—C14—C21	114.8 (2)	C211—C31—C321	122.5 (3)
C14—C15—C16	108.8 (2)	C41—C31—C211	119.4 (3)
N19—C16—C15	109.9 (2)	C41—C31—C321	118.0 (2)
C7—C16—C15	115.3 (2)	C31—C41—C51	120.0 (2)
N19—C16—C7	105.6 (2)	C41—C51—C61	120.0 (3)
C7—C17—C18	104.0 (2)	C51—C61—C111	120.3 (3)
N19—C18—C17	104.9 (2)	C121—C111—C211	120.4 (3)
N19—C20—C21	110.4 (2)	C61—C111—C121	120.4 (3)
C14—C21—C22	123.4 (2)	C61—C111—C211	119.2 (2)
C20—C21—C22	121.8 (3)	O111—C121—C111	117.1 (3)
C14—C21—C20	114.9 (2)	O111—C121—O121	123.2 (2)
C21—C22—C23	124.1 (3)	O121—C121—C111	119.7 (3)
O24—C23—C22	111.9 (2)	C31—C41—H41	120.00
C6—C1—H1	120.00	C51—C41—H41	120.00
C2—C1—H1	120.00	C61—C51—H51	120.00
C3—C4—H4	121.00	C41—C51—H51	120.00
C5—C4—H4	121.00	C111—C61—H61	120.00
N9—C8—H8	110.00	C51—C61—H61	120.00
C7—C8—H8	110.00	C31—C211—C111	121.0 (3)
C13—C8—H8	110.00	C31—C211—H211	119.00
C10—C11—H11B	108.00	C111—C211—H211	120.00
C10—C11—H11A	108.00	O321—C321—C31	114.2 (2)
C12—C11—H11B	108.00	O311—C321—O321	123.8 (3)
C12—C11—H11A	108.00	O311—C321—C31	122.0 (3)
C26—O2—C2—C1	0.8 (4)	C17—C7—C8—N9	106.0 (2)
C26—O2—C2—C3	179.8 (3)	C17—C7—C8—C13	−137.7 (2)
C27—O3—C3—C2	171.6 (3)	C6—C7—C16—N19	151.5 (2)
C27—O3—C3—C4	−7.5 (5)	C6—C7—C16—C15	−86.9 (3)
C23—O24—C12—C11	169.6 (2)	C8—C7—C16—N19	−89.1 (3)
C23—O24—C12—C13	−69.7 (3)	C8—C7—C16—C15	32.4 (3)
C12—O24—C23—C22	86.1 (3)	C17—C7—C16—N19	31.0 (2)
C10—N9—C5—C6	−156.8 (3)	C17—C7—C16—C15	152.6 (2)
C5—N9—C8—C7	10.6 (3)	C16—C7—C8—C13	−23.7 (3)
C10—N9—C8—C7	166.9 (3)	C16—C7—C17—C18	−41.5 (2)
C10—N9—C8—C13	42.3 (3)	C16—C7—C8—N9	−140.0 (2)
C5—N9—C8—C13	−114.0 (2)	C7—C8—C13—C14	39.3 (3)
C10—N9—C5—C4	26.3 (5)	C7—C8—C13—C12	171.6 (2)
C8—N9—C5—C6	−3.0 (3)	N9—C8—C13—C12	−72.7 (2)
C8—N9—C10—O25	−169.6 (3)	N9—C8—C13—C14	155.0 (2)
C8—N9—C10—C11	12.1 (4)	N9—C10—C11—C12	−38.1 (4)
C8—N9—C5—C4	−179.9 (3)	O25—C10—C11—C12	143.6 (3)
C5—N9—C10—C11	163.7 (3)	C10—C11—C12—C13	5.3 (4)
C5—N9—C10—O25	−18.0 (5)	C10—C11—C12—O24	128.4 (3)
C18—N19—C16—C7	−9.6 (3)	O24—C12—C13—C8	−70.0 (3)
C18—N19—C16—C15	−134.5 (2)	O24—C12—C13—C14	58.6 (4)
C16—N19—C20—C21	−46.3 (3)	C11—C12—C13—C14	176.3 (3)
C18—N19—C20—C21	74.6 (3)	C11—C12—C13—C8	47.8 (3)
C20—N19—C16—C7	113.8 (2)	C8—C13—C14—C21	60.2 (3)
C16—N19—C18—C17	−16.5 (3)	C12—C13—C14—C15	173.3 (3)
C20—N19—C18—C17	−140.9 (2)	C12—C13—C14—C21	−65.5 (3)
C20—N19—C16—C15	−11.1 (3)	C8—C13—C14—C15	−61.0 (3)
C6—C1—C2—O2	−178.7 (3)	C21—C14—C15—C16	−55.2 (3)
C2—C1—C6—C7	−170.8 (3)	C13—C14—C21—C20	−123.0 (3)
C2—C1—C6—C5	0.0 (5)	C13—C14—C15—C16	69.4 (3)
C6—C1—C2—C3	2.4 (5)	C13—C14—C21—C22	55.1 (4)
C1—C2—C3—O3	177.7 (3)	C15—C14—C21—C22	174.6 (3)
C1—C2—C3—C4	−3.2 (5)	C15—C14—C21—C20	−3.5 (4)
O2—C2—C3—O3	−1.4 (4)	C14—C15—C16—C7	−56.2 (3)
O2—C2—C3—C4	177.8 (3)	C14—C15—C16—N19	63.0 (3)
O3—C3—C4—C5	−179.5 (3)	C7—C17—C18—N19	36.5 (2)
C2—C3—C4—C5	1.4 (5)	N19—C20—C21—C22	−123.4 (3)
C3—C4—C5—N9	177.6 (3)	N19—C20—C21—C14	54.7 (3)
C3—C4—C5—C6	1.0 (5)	C20—C21—C22—C23	175.8 (3)
N9—C5—C6—C1	−178.9 (3)	C14—C21—C22—C23	−2.1 (5)
N9—C5—C6—C7	−6.6 (4)	C21—C22—C23—O24	−61.3 (4)
C4—C5—C6—C1	−1.8 (5)	C41—C31—C321—O311	−9.8 (4)
C4—C5—C6—C7	170.5 (3)	C211—C31—C41—C51	1.7 (4)
C1—C6—C7—C8	−175.8 (3)	C321—C31—C41—C51	−174.5 (2)
C1—C6—C7—C17	64.3 (4)	C211—C31—C321—O321	−4.6 (4)
C1—C6—C7—C16	−50.5 (4)	C41—C31—C211—C111	−1.7 (4)
C5—C6—C7—C8	12.7 (3)	C321—C31—C211—C111	174.3 (2)
C5—C6—C7—C16	138.0 (3)	C41—C31—C321—O321	171.5 (2)
C5—C6—C7—C17	−107.2 (3)	C211—C31—C321—O311	174.2 (3)
C6—C7—C8—N9	−13.5 (3)	C31—C41—C51—C61	0.8 (4)
C6—C7—C8—C13	102.8 (3)	C41—C51—C61—C111	−3.3 (4)
C6—C7—C17—C18	−165.3 (2)	C51—C61—C111—C121	−179.9 (2)
C8—C7—C17—C18	80.2 (2)	C51—C61—C111—C211	3.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N19—H19···O111^i	0.91 (3)	1.73 (3)	2.629 (3)	173 (4)
N19—H19···O121^i	0.91 (3)	2.57 (4)	3.217 (3)	129 (3)
O321—H321···O1W^ii	0.92 (6)	1.73 (6)	2.646 (3)	178 (7)
O1W—H11W···O25^iii	0.90 (3)	1.95 (3)	2.818 (3)	162 (4)
O1W—H12W···O121^iv	0.90 (3)	1.95 (3)	2.841 (3)	179 (4)
O2W—H21W···O111^i	0.85 (5)	2.19 (5)	2.780 (4)	126 (4)
O2W—H22W···O2W^v	0.85 (6)	2.42 (6)	2.817 (5)	110 (5)
O3WA—H31W···O121	0.91 (6)	1.91 (6)	2.822 (10)	178 (8)
O3WA—H32W···O2W^vi	0.90 (7)	1.85 (7)	2.705 (7)	157 (6)
O3WB—H33W···O121	0.90 (7)	1.77 (7)	2.667 (10)	179 (5)
O3WB—H34W···O2W^vi	0.89 (7)	1.86 (7)	2.752 (11)	179 (5)
C1—H1···O311^vii	0.95	2.27	3.182 (3)	160
C4—H4···O25	0.95	2.41	2.937 (3)	114
C8—H8···O24	1.00	2.58	3.000 (3)	105
C14—H14···O3^viii	1.00	2.36	3.361 (4)	176
C16—H16···O311^vii	1.00	2.58	3.411 (3)	140
C17—H17B···O2^ix	0.99	2.52	3.454 (3)	157
C26—H26B···O24^iii	0.98	2.53	3.260 (3)	131

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