Brucinium benzoate trihydrate

The title compound, C₂₃H₂₇N₂O₄⁺·C₇H₅O₂⁻·3H₂O contains two brucinium–benzoate ion pairs and six water mol­ecules in the asymmetric unit. In the crystal structure of (I), corrugated layers of brucinium cations, stabilized by weak C—H...O and C—H...π inter­actions, are separated by anionic/water sheets. The cationic and the anionic/water layers are linked by O—H...O, C—H...O and N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.083
• wR factor = 0.134
• Data-to-parameter ratio = 8.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H21W   ..  H31W    ..       2.05 Ang.

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.109
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.11
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          5
              H2 O

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           26.00
           From the CIF: _reflns_number_total               5934
           Count of symmetry unique reflns         5958
           Completeness (_total/calc)             99.60%
           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
PLAT791_ALERT_1_G Confirm the Absolute Configuration of N2     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of N2A    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7A    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8A    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11A   = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C18    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C18A   = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C19    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C19A   = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C21    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C21A   = .          S

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

  14 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
   3 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: 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.

brucinium benzoate trihydrate

Crystal data

C23H27N2O4^+·C7H5O2^−·3H2O	F(000) = 2432
Mr = 570.62	Dx = 1.385 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6452 reflections
a = 12.479 (2) Å	θ = 3.3–26.1°
b = 14.978 (2) Å	µ = 0.10 mm^−1
c = 29.272 (3) Å	T = 100 K
V = 5471.2 (13) Å^3	Plate, colourless
Z = 8	0.30 × 0.25 × 0.10 mm

Data collection

Kuma KM4CCD diffractometer	4492 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.109
Graphite monochromator	θmax = 26.0°, θmin = 3.3°
ω scan	h = −15→11
34091 measured reflections	k = −18→18
5934 independent reflections	l = −36→36

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)] = 0.083	Hydrogen site location: geom and difmap
wR(F^2) = 0.134	H-atom parameters constrained
S = 1.19	w = 1/[σ^2(Fo^2) + (0.0431P)^2] where P = (Fo^2 + 2Fc^2)/3
5934 reflections	(Δ/σ)max < 0.001
739 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.27 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
O1	0.3695 (3)	0.1096 (3)	0.59004 (13)	0.0244 (10)
O2	0.9168 (3)	0.1611 (3)	0.40645 (13)	0.0196 (10)
O3	1.0392 (3)	0.1278 (3)	0.47582 (13)	0.0204 (10)
O4	0.5308 (3)	0.1226 (3)	0.44501 (14)	0.0259 (11)
N1	0.6061 (3)	0.1673 (3)	0.51243 (15)	0.0150 (11)
N2	0.7165 (4)	0.1844 (3)	0.66210 (16)	0.0212 (12)
H2	0.7748	0.1947	0.6812	0.025*
C1	0.7568 (5)	0.1684 (4)	0.45360 (19)	0.0187 (14)
H1	0.7108	0.1758	0.4280	0.022*
C2	0.8660 (5)	0.1595 (4)	0.44818 (19)	0.0170 (14)
C3	0.9338 (4)	0.1458 (4)	0.4862 (2)	0.0190 (14)
C4	0.8935 (4)	0.1494 (4)	0.52996 (19)	0.0157 (13)
H4	0.9394	0.1431	0.5556	0.019*
C5	0.7829 (5)	0.1626 (4)	0.53570 (19)	0.0183 (14)
C6	0.7166 (5)	0.1662 (4)	0.4981 (2)	0.0203 (14)
C7	0.7189 (5)	0.1795 (4)	0.57894 (19)	0.0166 (14)
C8	0.6017 (5)	0.1597 (4)	0.56324 (18)	0.0166 (14)
H8	0.5519	0.2057	0.5759	0.020*
C9	0.5245 (5)	0.1311 (4)	0.4871 (2)	0.0201 (14)
C10	0.4250 (5)	0.1055 (4)	0.5128 (2)	0.0220 (15)
H10A	0.3832	0.0637	0.4936	0.026*
H10B	0.3810	0.1598	0.5171	0.026*
C11	0.4421 (5)	0.0614 (4)	0.56025 (19)	0.0180 (14)
H11	0.4194	−0.0026	0.5587	0.022*
C12	0.3610 (5)	0.0723 (5)	0.6351 (2)	0.0291 (17)
H12A	0.3713	0.0069	0.6336	0.035*
H12B	0.2884	0.0840	0.6475	0.035*
C13	0.4433 (5)	0.1123 (4)	0.6663 (2)	0.0221 (15)
H13	0.4204	0.1489	0.6910	0.027*
C14	0.5475 (5)	0.0978 (4)	0.6604 (2)	0.0214 (15)
C15	0.6300 (5)	0.1403 (4)	0.69049 (19)	0.0221 (15)
H15A	0.6625	0.0943	0.7104	0.027*
H15B	0.5953	0.1855	0.7103	0.027*
C16	0.6811 (5)	0.2741 (4)	0.6432 (2)	0.0240 (15)
H16A	0.7092	0.3238	0.6620	0.029*
H16B	0.6020	0.2783	0.6420	0.029*
C17	0.7292 (5)	0.2759 (4)	0.59526 (19)	0.0203 (14)
H17A	0.8052	0.2948	0.5961	0.024*
H17B	0.6887	0.3170	0.5751	0.024*
C18	0.5599 (5)	0.0659 (4)	0.5746 (2)	0.0198 (15)
H18	0.5987	0.0246	0.5534	0.024*
C19	0.5901 (5)	0.0356 (4)	0.6226 (2)	0.0188 (14)
H19	0.5609	−0.0258	0.6277	0.023*
C20	0.7121 (5)	0.0322 (4)	0.6260 (2)	0.0202 (15)
H20A	0.7415	−0.0056	0.6013	0.024*
H20B	0.7336	0.0061	0.6557	0.024*
C21	0.7566 (5)	0.1276 (4)	0.62178 (18)	0.0198 (14)
H21	0.8367	0.1255	0.6223	0.024*
C22	0.8503 (5)	0.1797 (4)	0.3676 (2)	0.0260 (16)
H22A	0.8941	0.1791	0.3398	0.039*
H22B	0.8172	0.2387	0.3712	0.039*
H22C	0.7942	0.1342	0.3653	0.039*
C23	1.1081 (5)	0.1049 (4)	0.5137 (2)	0.0286 (16)
H23A	1.1808	0.0935	0.5024	0.043*
H23B	1.0806	0.0513	0.5288	0.043*
H23C	1.1097	0.1545	0.5355	0.043*
O5	0.8627 (3)	0.1867 (3)	0.72977 (14)	0.0239 (10)
O6	0.8372 (3)	0.3336 (3)	0.72609 (14)	0.0264 (10)
C24	0.8783 (5)	0.2646 (4)	0.7445 (2)	0.0220 (15)
C25	0.9486 (5)	0.2770 (4)	0.78585 (19)	0.0191 (14)
C26	0.9903 (4)	0.2031 (4)	0.8086 (2)	0.0201 (15)
H26	0.9765	0.1448	0.7973	0.024*
C27	1.0525 (5)	0.2138 (5)	0.8480 (2)	0.0250 (16)
H27	1.0792	0.1630	0.8637	0.030*
C28	1.0750 (5)	0.2990 (4)	0.8641 (2)	0.0215 (15)
H28	1.1168	0.3067	0.8909	0.026*
C29	1.0366 (5)	0.3720 (4)	0.8410 (2)	0.0247 (15)
H29	1.0530	0.4302	0.8518	0.030*
C30	0.9735 (5)	0.3621 (4)	0.8018 (2)	0.0241 (15)
H30	0.9477	0.4133	0.7862	0.029*
O1A	−0.2475 (3)	0.8770 (3)	0.40617 (14)	0.0256 (10)
O2A	0.3107 (3)	0.8565 (3)	0.58529 (13)	0.0206 (10)
O3A	0.4323 (3)	0.8559 (3)	0.51327 (13)	0.0207 (10)
O4A	−0.0770 (3)	0.9160 (3)	0.54782 (13)	0.0232 (10)
N1A	−0.0070 (4)	0.8525 (3)	0.48394 (15)	0.0174 (11)
N2A	0.0938 (4)	0.8045 (3)	0.33372 (16)	0.0203 (12)
H2A	0.1524	0.7909	0.3154	0.024*
C1A	0.1466 (4)	0.8567 (4)	0.54006 (19)	0.0170 (13)
H1A	0.1016	0.8610	0.5661	0.020*
C2A	0.2587 (4)	0.8553 (4)	0.54444 (19)	0.0170 (13)
C3A	0.3241 (5)	0.8522 (4)	0.5054 (2)	0.0217 (15)
C4A	0.2779 (4)	0.8431 (4)	0.4622 (2)	0.0176 (14)
H4A	0.3220	0.8374	0.4359	0.021*
C5A	0.1667 (5)	0.8425 (4)	0.45797 (19)	0.0202 (14)
C6A	0.1041 (4)	0.8514 (4)	0.49646 (19)	0.0166 (13)
C7A	0.1003 (4)	0.8209 (4)	0.41653 (19)	0.0161 (14)
C8A	−0.0162 (4)	0.8453 (4)	0.43307 (18)	0.0165 (14)
H8A	−0.0666	0.7958	0.4250	0.020*
C9A	−0.0864 (5)	0.8926 (4)	0.5078 (2)	0.0179 (14)
C10A	−0.1909 (5)	0.9045 (4)	0.4816 (2)	0.0234 (15)
H10C	−0.2355	0.9483	0.4983	0.028*
H10D	−0.2297	0.8468	0.4821	0.028*
C11A	−0.1821 (5)	0.9354 (4)	0.4315 (2)	0.0194 (14)
H11A	−0.2108	0.9976	0.4288	0.023*
C12A	−0.2635 (5)	0.9035 (4)	0.3596 (2)	0.0265 (16)
H12C	−0.2621	0.9694	0.3576	0.032*
H12D	−0.3350	0.8830	0.3493	0.032*
C13A	−0.1792 (5)	0.8656 (4)	0.3286 (2)	0.0267 (16)
H13A	−0.2001	0.8250	0.3053	0.032*
C14A	−0.0761 (5)	0.8870 (4)	0.3326 (2)	0.0242 (15)
C15A	0.0082 (5)	0.8441 (4)	0.3034 (2)	0.0258 (15)
H15C	0.0404	0.8891	0.2827	0.031*
H15D	−0.0244	0.7966	0.2844	0.031*
C16A	0.0580 (5)	0.7197 (4)	0.35626 (19)	0.0195 (14)
H16C	0.0833	0.6671	0.3389	0.023*
H16D	−0.0212	0.7175	0.3583	0.023*
C17A	0.1073 (4)	0.7217 (4)	0.40319 (19)	0.0185 (14)
H17C	0.1826	0.7010	0.4024	0.022*
H17D	0.0664	0.6839	0.4248	0.022*
C18A	−0.0627 (4)	0.9345 (4)	0.41673 (19)	0.0168 (14)
H18A	−0.0267	0.9815	0.4355	0.020*
C19A	−0.0348 (5)	0.9560 (4)	0.3668 (2)	0.0197 (15)
H19A	−0.0646	1.0159	0.3588	0.024*
C20A	0.0879 (5)	0.9599 (4)	0.3645 (2)	0.0214 (15)
H20C	0.1107	0.9835	0.3345	0.026*
H20D	0.1155	1.0003	0.3886	0.026*
C21A	0.1326 (5)	0.8680 (4)	0.37129 (19)	0.0169 (14)
H21A	0.2125	0.8715	0.3699	0.020*
C22A	0.2443 (5)	0.8534 (4)	0.62532 (19)	0.0253 (15)
H22D	0.2896	0.8553	0.6527	0.038*
H22E	0.2025	0.7981	0.6253	0.038*
H22F	0.1957	0.9048	0.6254	0.038*
C23A	0.5000 (4)	0.8565 (4)	0.4739 (2)	0.0249 (15)
H23D	0.5751	0.8597	0.4835	0.037*
H23E	0.4829	0.9085	0.4549	0.037*
H23F	0.4885	0.8017	0.4562	0.037*
O5A	0.2400 (3)	0.7536 (3)	0.27631 (14)	0.0261 (11)
O6A	0.2666 (3)	0.8999 (3)	0.26967 (14)	0.0258 (10)
C24A	0.2817 (5)	0.8191 (5)	0.2561 (2)	0.0217 (15)
C25A	0.3476 (4)	0.8025 (4)	0.2146 (2)	0.0193 (14)
C26A	0.3854 (5)	0.8731 (4)	0.1882 (2)	0.0263 (16)
H26A	0.3726	0.9327	0.1978	0.032*
C27A	0.4419 (5)	0.8573 (4)	0.1478 (2)	0.0233 (15)
H27A	0.4674	0.9059	0.1300	0.028*
C28A	0.4606 (5)	0.7706 (4)	0.1338 (2)	0.0271 (16)
H28A	0.4972	0.7592	0.1060	0.033*
C29A	0.4251 (5)	0.6996 (4)	0.1611 (2)	0.0232 (15)
H29A	0.4406	0.6399	0.1523	0.028*
C30A	0.3681 (5)	0.7152 (4)	0.2005 (2)	0.0227 (15)
H30A	0.3426	0.6665	0.2182	0.027*
O1W	1.1387 (3)	0.5148 (3)	0.73744 (16)	0.0384 (13)
H11W	1.1463	0.5683	0.7495	0.058*
H12W	1.0752	0.5037	0.7257	0.058*
O2W	0.3173 (3)	0.4230 (3)	0.76760 (16)	0.0348 (12)
H21W	0.2996	0.3664	0.7705	0.052*
H22W	0.2608	0.4528	0.7581	0.052*
O3W	0.5108 (4)	0.3468 (3)	0.73231 (15)	0.0433 (13)
H31W	0.4507	0.3696	0.7429	0.065*
H32W	0.5661	0.3762	0.7434	0.065*
O4W	0.6861 (3)	0.4417 (3)	0.76895 (15)	0.0370 (12)
H41W	0.7360	0.4038	0.7603	0.056*
H42W	0.7110	0.4915	0.7570	0.056*
O5W	0.8763 (4)	0.4878 (3)	0.60387 (15)	0.0381 (13)
H51W	0.8975	0.4360	0.5930	0.057*
H52W	0.8918	0.4885	0.6332	0.057*
O6W	0.9305 (3)	0.4881 (3)	0.69924 (14)	0.0273 (11)
H61W	0.8816	0.5284	0.7059	0.041*
H62W	0.9010	0.4374	0.7078	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.024 (2)	0.027 (3)	0.022 (2)	−0.001 (2)	0.005 (2)	−0.003 (2)
O2	0.017 (2)	0.023 (2)	0.019 (2)	−0.0002 (19)	0.0010 (19)	−0.0032 (19)
O3	0.015 (2)	0.030 (3)	0.016 (2)	0.0007 (19)	−0.0012 (17)	−0.0011 (19)
O4	0.025 (2)	0.033 (3)	0.019 (2)	−0.006 (2)	−0.0029 (19)	−0.005 (2)
N1	0.007 (2)	0.025 (3)	0.013 (3)	0.000 (2)	−0.001 (2)	−0.001 (2)
N2	0.023 (3)	0.024 (3)	0.017 (3)	0.009 (2)	−0.004 (2)	−0.003 (2)
C1	0.025 (4)	0.019 (3)	0.012 (3)	0.002 (3)	0.003 (3)	0.001 (3)
C2	0.018 (3)	0.016 (3)	0.017 (3)	−0.004 (3)	0.004 (3)	0.001 (3)
C3	0.010 (3)	0.019 (3)	0.028 (4)	0.002 (3)	−0.001 (3)	−0.001 (3)
C4	0.019 (3)	0.013 (3)	0.015 (3)	−0.005 (3)	−0.002 (3)	0.001 (3)
C5	0.023 (3)	0.014 (3)	0.018 (3)	0.001 (3)	0.005 (3)	0.001 (3)
C6	0.021 (3)	0.017 (3)	0.023 (4)	−0.002 (3)	0.001 (3)	0.003 (3)
C7	0.016 (3)	0.012 (3)	0.021 (3)	0.002 (3)	−0.003 (3)	−0.002 (3)
C8	0.017 (3)	0.017 (3)	0.016 (3)	−0.005 (3)	−0.001 (3)	−0.004 (3)
C9	0.020 (3)	0.018 (3)	0.022 (4)	0.005 (3)	0.001 (3)	−0.002 (3)
C10	0.022 (3)	0.018 (3)	0.026 (4)	−0.003 (3)	−0.001 (3)	0.003 (3)
C11	0.014 (3)	0.018 (3)	0.023 (4)	−0.003 (3)	0.000 (3)	−0.002 (3)
C12	0.029 (4)	0.028 (4)	0.030 (4)	−0.006 (3)	0.009 (3)	−0.001 (3)
C13	0.023 (4)	0.020 (4)	0.024 (4)	0.005 (3)	0.004 (3)	0.004 (3)
C14	0.030 (4)	0.015 (3)	0.020 (3)	0.000 (3)	0.002 (3)	0.004 (3)
C15	0.026 (3)	0.028 (4)	0.012 (3)	0.000 (3)	0.004 (3)	0.001 (3)
C16	0.026 (4)	0.026 (4)	0.020 (4)	0.004 (3)	−0.001 (3)	−0.003 (3)
C17	0.022 (3)	0.024 (4)	0.015 (3)	−0.002 (3)	−0.004 (3)	−0.002 (3)
C18	0.021 (3)	0.012 (3)	0.026 (4)	0.003 (3)	0.005 (3)	−0.003 (3)
C19	0.020 (3)	0.019 (3)	0.017 (3)	0.000 (3)	0.004 (3)	0.005 (3)
C20	0.022 (3)	0.028 (4)	0.011 (3)	0.006 (3)	0.001 (3)	−0.003 (3)
C21	0.027 (4)	0.017 (3)	0.015 (3)	0.008 (3)	0.003 (3)	0.002 (3)
C22	0.029 (4)	0.033 (4)	0.016 (3)	0.000 (3)	−0.002 (3)	0.002 (3)
C23	0.013 (3)	0.035 (4)	0.038 (4)	0.002 (3)	0.003 (3)	0.005 (3)
O5	0.025 (2)	0.022 (3)	0.025 (2)	−0.001 (2)	−0.003 (2)	−0.002 (2)
O6	0.027 (2)	0.022 (3)	0.031 (3)	0.002 (2)	−0.003 (2)	0.001 (2)
C24	0.019 (4)	0.025 (4)	0.022 (4)	−0.004 (3)	0.008 (3)	0.001 (3)
C25	0.023 (3)	0.022 (4)	0.013 (3)	0.000 (3)	0.006 (3)	0.000 (3)
C26	0.016 (3)	0.027 (4)	0.017 (3)	−0.006 (3)	0.001 (3)	−0.005 (3)
C27	0.022 (4)	0.038 (4)	0.014 (3)	0.005 (3)	0.000 (3)	0.001 (3)
C28	0.016 (3)	0.027 (4)	0.022 (4)	−0.002 (3)	−0.004 (3)	−0.008 (3)
C29	0.025 (4)	0.021 (4)	0.028 (4)	−0.005 (3)	0.000 (3)	−0.006 (3)
C30	0.026 (4)	0.025 (4)	0.022 (4)	0.000 (3)	−0.002 (3)	0.002 (3)
O1A	0.023 (2)	0.031 (3)	0.023 (2)	−0.002 (2)	−0.008 (2)	0.002 (2)
O2A	0.018 (2)	0.030 (3)	0.014 (2)	−0.002 (2)	0.0009 (18)	0.005 (2)
O3A	0.013 (2)	0.026 (2)	0.023 (2)	0.000 (2)	0.0014 (18)	−0.001 (2)
O4A	0.021 (2)	0.033 (3)	0.015 (2)	0.002 (2)	0.0047 (19)	−0.001 (2)
N1A	0.012 (3)	0.020 (3)	0.020 (3)	−0.001 (2)	0.000 (2)	0.000 (2)
N2A	0.019 (3)	0.027 (3)	0.015 (3)	0.002 (2)	−0.003 (2)	−0.003 (2)
C1A	0.017 (3)	0.022 (4)	0.012 (3)	0.003 (3)	0.004 (3)	−0.002 (3)
C2A	0.021 (3)	0.017 (3)	0.013 (3)	0.002 (3)	−0.003 (3)	0.005 (3)
C3A	0.014 (3)	0.020 (4)	0.031 (4)	0.008 (3)	0.003 (3)	−0.006 (3)
C4A	0.007 (3)	0.019 (3)	0.026 (4)	0.002 (3)	0.002 (3)	0.003 (3)
C5A	0.028 (4)	0.018 (4)	0.015 (3)	0.006 (3)	0.003 (3)	−0.001 (3)
C6A	0.014 (3)	0.016 (3)	0.020 (3)	−0.002 (3)	0.003 (3)	0.005 (3)
C7A	0.013 (3)	0.020 (3)	0.016 (3)	0.002 (3)	−0.005 (3)	0.000 (3)
C8A	0.017 (3)	0.017 (3)	0.015 (3)	−0.003 (3)	0.000 (3)	−0.001 (3)
C9A	0.014 (3)	0.017 (3)	0.023 (4)	−0.003 (3)	0.005 (3)	0.004 (3)
C10A	0.017 (3)	0.028 (4)	0.025 (4)	0.005 (3)	0.002 (3)	0.001 (3)
C11A	0.017 (3)	0.018 (3)	0.024 (4)	−0.003 (3)	−0.008 (3)	−0.002 (3)
C12A	0.021 (4)	0.032 (4)	0.026 (4)	−0.002 (3)	−0.003 (3)	0.000 (3)
C13A	0.033 (4)	0.030 (4)	0.017 (3)	0.001 (3)	−0.015 (3)	−0.003 (3)
C14A	0.031 (4)	0.024 (4)	0.018 (3)	0.004 (3)	−0.009 (3)	0.000 (3)
C15A	0.030 (4)	0.032 (4)	0.016 (3)	0.004 (3)	−0.004 (3)	−0.001 (3)
C16A	0.024 (4)	0.016 (3)	0.019 (3)	−0.001 (3)	0.003 (3)	0.004 (3)
C17A	0.012 (3)	0.027 (4)	0.017 (3)	−0.005 (3)	0.002 (3)	−0.003 (3)
C18A	0.017 (3)	0.017 (3)	0.017 (3)	0.003 (3)	−0.003 (3)	−0.005 (3)
C19A	0.026 (4)	0.009 (3)	0.024 (4)	−0.001 (3)	−0.004 (3)	−0.007 (3)
C20A	0.019 (4)	0.026 (4)	0.019 (4)	−0.003 (3)	0.000 (3)	0.000 (3)
C21A	0.014 (3)	0.014 (3)	0.022 (3)	0.000 (3)	0.000 (3)	0.002 (3)
C22A	0.022 (3)	0.033 (4)	0.020 (3)	0.001 (3)	−0.005 (3)	−0.003 (3)
C23A	0.013 (3)	0.038 (4)	0.024 (4)	−0.004 (3)	0.005 (3)	0.003 (3)
O5A	0.033 (3)	0.019 (2)	0.026 (3)	−0.004 (2)	0.009 (2)	−0.001 (2)
O6A	0.027 (2)	0.023 (2)	0.027 (3)	−0.002 (2)	0.001 (2)	−0.002 (2)
C24A	0.015 (3)	0.031 (4)	0.019 (3)	−0.005 (3)	−0.006 (3)	0.000 (3)
C25A	0.011 (3)	0.029 (4)	0.017 (3)	−0.001 (3)	−0.001 (3)	0.002 (3)
C26A	0.028 (4)	0.025 (4)	0.025 (4)	0.000 (3)	−0.010 (3)	−0.001 (3)
C27A	0.021 (3)	0.024 (4)	0.025 (4)	−0.004 (3)	0.001 (3)	0.001 (3)
C28A	0.031 (4)	0.036 (4)	0.014 (3)	0.002 (3)	0.006 (3)	0.000 (3)
C29A	0.020 (3)	0.026 (4)	0.024 (4)	0.005 (3)	0.004 (3)	−0.002 (3)
C30A	0.017 (3)	0.026 (4)	0.024 (4)	−0.006 (3)	−0.004 (3)	0.002 (3)
O1W	0.027 (3)	0.026 (3)	0.063 (3)	0.000 (2)	−0.014 (3)	−0.003 (3)
O2W	0.032 (3)	0.020 (3)	0.052 (3)	−0.001 (2)	−0.016 (2)	−0.001 (2)
O3W	0.029 (3)	0.046 (3)	0.055 (3)	−0.006 (3)	−0.005 (2)	−0.017 (3)
O4W	0.032 (3)	0.035 (3)	0.044 (3)	0.002 (2)	0.007 (2)	0.001 (2)
O5W	0.048 (3)	0.037 (3)	0.030 (3)	0.009 (3)	0.000 (2)	0.002 (2)
O6W	0.026 (2)	0.021 (2)	0.035 (3)	−0.001 (2)	0.002 (2)	−0.001 (2)

Geometric parameters (Å, º)

O1—C12	1.437 (7)	O4A—C9A	1.228 (7)
O1—C11	1.450 (7)	N1A—C9A	1.352 (7)
O2—C2	1.376 (6)	N1A—C6A	1.434 (7)
O2—C22	1.435 (6)	N1A—C8A	1.498 (7)
O3—C3	1.376 (6)	N2A—C16A	1.499 (7)
O3—C23	1.443 (7)	N2A—C15A	1.510 (7)
O4—C9	1.240 (7)	N2A—C21A	1.532 (7)
N1—C9	1.371 (7)	N2A—H2A	0.9300
N1—C6	1.441 (7)	C1A—C6A	1.384 (7)
N1—C8	1.493 (6)	C1A—C2A	1.405 (7)
N2—C15	1.514 (7)	C1A—H1A	0.9500
N2—C16	1.519 (7)	C2A—C3A	1.404 (8)
N2—C21	1.539 (7)	C3A—C4A	1.398 (8)
N2—H2	0.9300	C4A—C5A	1.394 (7)
C1—C2	1.378 (8)	C4A—H4A	0.9500
C1—C6	1.397 (8)	C5A—C6A	1.378 (7)
C1—H1	0.9500	C5A—C7A	1.504 (8)
C2—C3	1.412 (8)	C7A—C17A	1.539 (8)
C3—C4	1.379 (8)	C7A—C21A	1.554 (8)
C4—C5	1.404 (8)	C7A—C8A	1.576 (8)
C4—H4	0.9500	C8A—C18A	1.533 (8)
C5—C6	1.378 (8)	C8A—H8A	1.0000
C5—C7	1.518 (8)	C9A—C10A	1.523 (8)
C7—C17	1.527 (8)	C10A—C11A	1.541 (8)
C7—C21	1.549 (8)	C10A—H10C	0.9900
C7—C8	1.562 (8)	C10A—H10D	0.9900
C8—C18	1.534 (8)	C11A—C18A	1.551 (8)
C8—H8	1.0000	C11A—H11A	1.0000
C9—C10	1.503 (8)	C12A—C13A	1.502 (8)
C10—C11	1.552 (8)	C12A—H12C	0.9900
C10—H10A	0.9900	C12A—H12D	0.9900
C10—H10B	0.9900	C13A—C14A	1.332 (8)
C11—C18	1.530 (8)	C13A—H13A	0.9500
C11—H11	1.0000	C14A—C15A	1.501 (8)
C12—C13	1.499 (8)	C14A—C19A	1.528 (8)
C12—H12A	0.9900	C15A—H15C	0.9900
C12—H12B	0.9900	C15A—H15D	0.9900
C13—C14	1.330 (8)	C16A—C17A	1.506 (8)
C13—H13	0.9500	C16A—H16C	0.9900
C14—C15	1.497 (8)	C16A—H16D	0.9900
C14—C19	1.541 (8)	C17A—H17C	0.9900
C15—H15A	0.9900	C17A—H17D	0.9900
C15—H15B	0.9900	C18A—C19A	1.536 (8)
C16—C17	1.525 (8)	C18A—H18A	1.0000
C16—H16A	0.9900	C19A—C20A	1.534 (8)
C16—H16B	0.9900	C19A—H19A	1.0000
C17—H17A	0.9900	C20A—C21A	1.497 (8)
C17—H17B	0.9900	C20A—H20C	0.9900
C18—C19	1.525 (8)	C20A—H20D	0.9900
C18—H18	1.0000	C21A—H21A	1.0000
C19—C20	1.526 (8)	C22A—H22D	0.9800
C19—H19	1.0000	C22A—H22E	0.9800
C20—C21	1.537 (8)	C22A—H22F	0.9800
C20—H20A	0.9900	C23A—H23D	0.9800
C20—H20B	0.9900	C23A—H23E	0.9800
C21—H21	1.0000	C23A—H23F	0.9800
C22—H22A	0.9800	O5A—C24A	1.258 (7)
C22—H22B	0.9800	O6A—C24A	1.288 (7)
C22—H22C	0.9800	C24A—C25A	1.488 (8)
C23—H23A	0.9800	C25A—C26A	1.392 (8)
C23—H23B	0.9800	C25A—C30A	1.393 (8)
C23—H23C	0.9800	C26A—C27A	1.399 (8)
O5—C24	1.259 (7)	C26A—H26A	0.9500
O6—C24	1.273 (7)	C27A—C28A	1.380 (8)
C24—C25	1.506 (8)	C27A—H27A	0.9500
C25—C30	1.394 (8)	C28A—C29A	1.403 (8)
C25—C26	1.393 (8)	C28A—H28A	0.9500
C26—C27	1.399 (8)	C29A—C30A	1.375 (8)
C26—H26	0.9500	C29A—H29A	0.9500
C27—C28	1.388 (8)	C30A—H30A	0.9500
C27—H27	0.9500	O1W—H11W	0.8800
C28—C29	1.371 (8)	O1W—H12W	0.8800
C28—H28	0.9500	O2W—H21W	0.8800
C29—C30	1.399 (8)	O2W—H22W	0.8800
C29—H29	0.9500	O3W—H31W	0.8800
C30—H30	0.9500	O3W—H32W	0.8800
O1A—C11A	1.409 (7)	O4W—H41W	0.8800
O1A—C12A	1.434 (7)	O4W—H42W	0.8801
O2A—C2A	1.360 (6)	O5W—H51W	0.8799
O2A—C22A	1.436 (6)	O5W—H52W	0.8801
O3A—C3A	1.371 (7)	O6W—H61W	0.8801
O3A—C23A	1.429 (6)	O6W—H62W	0.8800
C12—O1—C11	113.9 (5)	C9A—N1A—C6A	125.5 (5)
C2—O2—C22	116.1 (4)	C9A—N1A—C8A	119.3 (5)
C3—O3—C23	116.6 (4)	C6A—N1A—C8A	109.1 (4)
C9—N1—C6	123.2 (5)	C16A—N2A—C15A	112.3 (5)
C9—N1—C8	118.8 (5)	C16A—N2A—C21A	107.7 (4)
C6—N1—C8	109.0 (4)	C15A—N2A—C21A	113.7 (5)
C15—N2—C16	112.2 (5)	C16A—N2A—H2A	107.6
C15—N2—C21	114.3 (5)	C15A—N2A—H2A	107.6
C16—N2—C21	107.7 (4)	C21A—N2A—H2A	107.6
C15—N2—H2	107.4	C6A—C1A—C2A	117.7 (5)
C16—N2—H2	107.4	C6A—C1A—H1A	121.1
C21—N2—H2	107.4	C2A—C1A—H1A	121.1
C2—C1—C6	117.4 (5)	O2A—C2A—C3A	116.0 (5)
C2—C1—H1	121.3	O2A—C2A—C1A	123.7 (5)
C6—C1—H1	121.3	C3A—C2A—C1A	120.3 (5)
O2—C2—C1	123.8 (5)	O3A—C3A—C4A	124.1 (5)
O2—C2—C3	115.2 (5)	O3A—C3A—C2A	115.8 (5)
C1—C2—C3	121.1 (5)	C4A—C3A—C2A	120.1 (5)
O3—C3—C4	124.1 (5)	C5A—C4A—C3A	119.4 (5)
O3—C3—C2	115.4 (5)	C5A—C4A—H4A	120.3
C4—C3—C2	120.5 (5)	C3A—C4A—H4A	120.3
C3—C4—C5	118.4 (5)	C6A—C5A—C4A	119.5 (6)
C3—C4—H4	120.8	C6A—C5A—C7A	111.6 (5)
C5—C4—H4	120.8	C4A—C5A—C7A	128.4 (5)
C6—C5—C4	120.0 (5)	C5A—C6A—C1A	122.8 (5)
C6—C5—C7	110.1 (5)	C5A—C6A—N1A	109.9 (5)
C4—C5—C7	129.8 (5)	C1A—C6A—N1A	127.3 (5)
C5—C6—C1	122.0 (6)	C5A—C7A—C17A	112.4 (5)
C5—C6—N1	110.0 (5)	C5A—C7A—C21A	116.5 (5)
C1—C6—N1	128.0 (5)	C17A—C7A—C21A	102.0 (4)
C5—C7—C17	112.0 (5)	C5A—C7A—C8A	102.1 (4)
C5—C7—C21	115.6 (5)	C17A—C7A—C8A	110.7 (5)
C17—C7—C21	101.3 (4)	C21A—C7A—C8A	113.3 (5)
C5—C7—C8	102.4 (4)	N1A—C8A—C18A	106.0 (4)
C17—C7—C8	110.5 (5)	N1A—C8A—C7A	104.6 (4)
C21—C7—C8	115.3 (5)	C18A—C8A—C7A	117.1 (5)
N1—C8—C18	107.3 (4)	N1A—C8A—H8A	109.6
N1—C8—C7	104.1 (4)	C18A—C8A—H8A	109.6
C18—C8—C7	115.4 (5)	C7A—C8A—H8A	109.6
N1—C8—H8	109.9	O4A—C9A—N1A	123.3 (5)
C18—C8—H8	109.9	O4A—C9A—C10A	121.9 (5)
C7—C8—H8	109.9	N1A—C9A—C10A	114.8 (5)
O4—C9—N1	122.1 (5)	C9A—C10A—C11A	116.9 (5)
O4—C9—C10	121.6 (5)	C9A—C10A—H10C	108.1
N1—C9—C10	116.3 (5)	C11A—C10A—H10C	108.1
C9—C10—C11	116.3 (5)	C9A—C10A—H10D	108.1
C9—C10—H10A	108.2	C11A—C10A—H10D	108.1
C11—C10—H10A	108.2	H10C—C10A—H10D	107.3
C9—C10—H10B	108.2	O1A—C11A—C10A	105.8 (5)
C11—C10—H10B	108.2	O1A—C11A—C18A	113.8 (5)
H10A—C10—H10B	107.4	C10A—C11A—C18A	109.4 (5)
O1—C11—C18	114.5 (5)	O1A—C11A—H11A	109.3
O1—C11—C10	103.9 (5)	C10A—C11A—H11A	109.3
C18—C11—C10	111.0 (5)	C18A—C11A—H11A	109.3
O1—C11—H11	109.1	O1A—C12A—C13A	111.9 (5)
C18—C11—H11	109.1	O1A—C12A—H12C	109.2
C10—C11—H11	109.1	C13A—C12A—H12C	109.2
O1—C12—C13	110.7 (5)	O1A—C12A—H12D	109.2
O1—C12—H12A	109.5	C13A—C12A—H12D	109.2
C13—C12—H12A	109.5	H12C—C12A—H12D	107.9
O1—C12—H12B	109.5	C14A—C13A—C12A	122.1 (6)
C13—C12—H12B	109.5	C14A—C13A—H13A	118.9
H12A—C12—H12B	108.1	C12A—C13A—H13A	118.9
C14—C13—C12	121.7 (6)	C13A—C14A—C15A	121.5 (6)
C14—C13—H13	119.2	C13A—C14A—C19A	123.2 (6)
C12—C13—H13	119.2	C15A—C14A—C19A	115.3 (5)
C13—C14—C15	121.7 (6)	C14A—C15A—N2A	109.2 (5)
C13—C14—C19	122.0 (6)	C14A—C15A—H15C	109.8
C15—C14—C19	116.3 (5)	N2A—C15A—H15C	109.8
C14—C15—N2	110.6 (5)	C14A—C15A—H15D	109.8
C14—C15—H15A	109.5	N2A—C15A—H15D	109.8
N2—C15—H15A	109.5	H15C—C15A—H15D	108.3
C14—C15—H15B	109.5	N2A—C16A—C17A	105.3 (5)
N2—C15—H15B	109.5	N2A—C16A—H16C	110.7
H15A—C15—H15B	108.1	C17A—C16A—H16C	110.7
N2—C16—C17	103.7 (5)	N2A—C16A—H16D	110.7
N2—C16—H16A	111.0	C17A—C16A—H16D	110.7
C17—C16—H16A	111.0	H16C—C16A—H16D	108.8
N2—C16—H16B	111.0	C16A—C17A—C7A	103.1 (5)
C17—C16—H16B	111.0	C16A—C17A—H17C	111.1
H16A—C16—H16B	109.0	C7A—C17A—H17C	111.1
C16—C17—C7	103.7 (5)	C16A—C17A—H17D	111.1
C16—C17—H17A	111.0	C7A—C17A—H17D	111.1
C7—C17—H17A	111.0	H17C—C17A—H17D	109.1
C16—C17—H17B	111.0	C8A—C18A—C19A	113.2 (5)
C7—C17—H17B	111.0	C8A—C18A—C11A	106.5 (5)
H17A—C17—H17B	109.0	C19A—C18A—C11A	118.8 (5)
C19—C18—C11	118.5 (5)	C8A—C18A—H18A	105.8
C19—C18—C8	112.8 (5)	C19A—C18A—H18A	105.8
C11—C18—C8	107.9 (5)	C11A—C18A—H18A	105.8
C19—C18—H18	105.5	C14A—C19A—C20A	109.5 (5)
C11—C18—H18	105.5	C14A—C19A—C18A	113.9 (5)
C8—C18—H18	105.5	C20A—C19A—C18A	106.0 (5)
C18—C19—C20	108.4 (5)	C14A—C19A—H19A	109.1
C18—C19—C14	113.3 (5)	C20A—C19A—H19A	109.1
C20—C19—C14	108.5 (5)	C18A—C19A—H19A	109.1
C18—C19—H19	108.8	C21A—C20A—C19A	109.3 (5)
C20—C19—H19	108.8	C21A—C20A—H20C	109.8
C14—C19—H19	108.8	C19A—C20A—H20C	109.8
C19—C20—C21	109.0 (5)	C21A—C20A—H20D	109.8
C19—C20—H20A	109.9	C19A—C20A—H20D	109.8
C21—C20—H20A	109.9	H20C—C20A—H20D	108.3
C19—C20—H20B	109.9	C20A—C21A—N2A	111.0 (5)
C21—C20—H20B	109.9	C20A—C21A—C7A	115.7 (5)
H20A—C20—H20B	108.3	N2A—C21A—C7A	104.3 (4)
C20—C21—N2	109.6 (5)	C20A—C21A—H21A	108.5
C20—C21—C7	114.9 (5)	N2A—C21A—H21A	108.5
N2—C21—C7	104.2 (4)	C7A—C21A—H21A	108.5
C20—C21—H21	109.3	O2A—C22A—H22D	109.5
N2—C21—H21	109.3	O2A—C22A—H22E	109.5
C7—C21—H21	109.3	H22D—C22A—H22E	109.5
O2—C22—H22A	109.5	O2A—C22A—H22F	109.5
O2—C22—H22B	109.5	H22D—C22A—H22F	109.5
H22A—C22—H22B	109.5	H22E—C22A—H22F	109.5
O2—C22—H22C	109.5	O3A—C23A—H23D	109.5
H22A—C22—H22C	109.5	O3A—C23A—H23E	109.5
H22B—C22—H22C	109.5	H23D—C23A—H23E	109.5
O3—C23—H23A	109.5	O3A—C23A—H23F	109.5
O3—C23—H23B	109.5	H23D—C23A—H23F	109.5
H23A—C23—H23B	109.5	H23E—C23A—H23F	109.5
O3—C23—H23C	109.5	O5A—C24A—O6A	121.8 (6)
H23A—C23—H23C	109.5	O5A—C24A—C25A	118.8 (6)
H23B—C23—H23C	109.5	O6A—C24A—C25A	119.4 (6)
O5—C24—O6	123.0 (6)	C26A—C25A—C30A	119.1 (6)
O5—C24—C25	118.6 (6)	C26A—C25A—C24A	120.8 (6)
O6—C24—C25	118.4 (6)	C30A—C25A—C24A	120.0 (6)
C30—C25—C26	118.9 (5)	C25A—C26A—C27A	120.8 (6)
C30—C25—C24	120.8 (6)	C25A—C26A—H26A	119.6
C26—C25—C24	120.3 (6)	C27A—C26A—H26A	119.6
C25—C26—C27	120.7 (6)	C28A—C27A—C26A	119.6 (6)
C25—C26—H26	119.7	C28A—C27A—H27A	120.2
C27—C26—H26	119.7	C26A—C27A—H27A	120.2
C28—C27—C26	119.8 (6)	C27A—C28A—C29A	119.4 (6)
C28—C27—H27	120.1	C27A—C28A—H28A	120.3
C26—C27—H27	120.1	C29A—C28A—H28A	120.3
C29—C28—C27	119.7 (6)	C30A—C29A—C28A	120.8 (6)
C29—C28—H28	120.2	C30A—C29A—H29A	119.6
C27—C28—H28	120.2	C28A—C29A—H29A	119.6
C28—C29—C30	121.1 (6)	C29A—C30A—C25A	120.2 (6)
C28—C29—H29	119.5	C29A—C30A—H30A	119.9
C30—C29—H29	119.5	C25A—C30A—H30A	119.9
C25—C30—C29	119.8 (6)	H11W—O1W—H12W	115.2
C25—C30—H30	120.1	H21W—O2W—H22W	108.6
C29—C30—H30	120.1	H31W—O3W—H32W	110.1
C11A—O1A—C12A	114.2 (5)	H41W—O4W—H42W	100.5
C2A—O2A—C22A	116.2 (4)	H51W—O5W—H52W	107.2
C3A—O3A—C23A	116.6 (4)	H61W—O6W—H62W	103.9
C22—O2—C2—C1	4.7 (8)	C22A—O2A—C2A—C3A	−175.9 (5)
C22—O2—C2—C3	−176.8 (5)	C22A—O2A—C2A—C1A	4.0 (8)
C6—C1—C2—O2	−179.5 (5)	C6A—C1A—C2A—O2A	−177.4 (5)
C6—C1—C2—C3	2.0 (9)	C6A—C1A—C2A—C3A	2.4 (9)
C23—O3—C3—C4	4.8 (8)	C23A—O3A—C3A—C4A	4.4 (9)
C23—O3—C3—C2	−174.2 (5)	C23A—O3A—C3A—C2A	−177.6 (5)
O2—C2—C3—O3	−5.7 (8)	O2A—C2A—C3A—O3A	−3.5 (8)
C1—C2—C3—O3	172.8 (5)	C1A—C2A—C3A—O3A	176.6 (5)
O2—C2—C3—C4	175.3 (5)	O2A—C2A—C3A—C4A	174.6 (5)
C1—C2—C3—C4	−6.2 (9)	C1A—C2A—C3A—C4A	−5.3 (9)
O3—C3—C4—C5	−175.8 (5)	O3A—C3A—C4A—C5A	−178.3 (6)
C2—C3—C4—C5	3.1 (9)	C2A—C3A—C4A—C5A	3.8 (9)
C3—C4—C5—C6	3.9 (9)	C3A—C4A—C5A—C6A	0.4 (9)
C3—C4—C5—C7	−172.4 (6)	C3A—C4A—C5A—C7A	−170.6 (6)
C4—C5—C6—C1	−8.2 (9)	C4A—C5A—C6A—C1A	−3.4 (10)
C7—C5—C6—C1	168.7 (5)	C7A—C5A—C6A—C1A	169.1 (5)
C4—C5—C6—N1	171.8 (5)	C4A—C5A—C6A—N1A	177.7 (6)
C7—C5—C6—N1	−11.2 (7)	C7A—C5A—C6A—N1A	−9.9 (7)
C2—C1—C6—C5	5.1 (9)	C2A—C1A—C6A—C5A	1.9 (9)
C2—C1—C6—N1	−174.9 (6)	C2A—C1A—C6A—N1A	−179.4 (6)
C9—N1—C6—C5	−149.2 (5)	C9A—N1A—C6A—C5A	−153.2 (6)
C8—N1—C6—C5	−2.7 (7)	C8A—N1A—C6A—C5A	−1.1 (7)
C9—N1—C6—C1	30.9 (9)	C9A—N1A—C6A—C1A	28.0 (10)
C8—N1—C6—C1	177.4 (6)	C8A—N1A—C6A—C1A	−179.9 (6)
C6—C5—C7—C17	−98.9 (6)	C6A—C5A—C7A—C17A	−103.0 (6)
C4—C5—C7—C17	77.7 (8)	C4A—C5A—C7A—C17A	68.6 (8)
C6—C5—C7—C21	145.8 (5)	C6A—C5A—C7A—C21A	139.8 (5)
C4—C5—C7—C21	−37.6 (9)	C4A—C5A—C7A—C21A	−48.7 (9)
C6—C5—C7—C8	19.6 (6)	C6A—C5A—C7A—C8A	15.8 (6)
C4—C5—C7—C8	−163.9 (6)	C4A—C5A—C7A—C8A	−172.7 (6)
C9—N1—C8—C18	40.1 (7)	C9A—N1A—C8A—C18A	40.4 (6)
C6—N1—C8—C18	−108.1 (5)	C6A—N1A—C8A—C18A	−113.7 (5)
C9—N1—C8—C7	162.8 (5)	C9A—N1A—C8A—C7A	164.8 (5)
C6—N1—C8—C7	14.7 (6)	C6A—N1A—C8A—C7A	10.7 (6)
C5—C7—C8—N1	−19.9 (6)	C5A—C7A—C8A—N1A	−15.3 (6)
C17—C7—C8—N1	99.5 (5)	C17A—C7A—C8A—N1A	104.6 (5)
C21—C7—C8—N1	−146.3 (5)	C21A—C7A—C8A—N1A	−141.4 (5)
C5—C7—C8—C18	97.4 (5)	C5A—C7A—C8A—C18A	101.7 (5)
C17—C7—C8—C18	−143.1 (5)	C17A—C7A—C8A—C18A	−138.4 (5)
C21—C7—C8—C18	−29.0 (7)	C21A—C7A—C8A—C18A	−24.5 (7)
C6—N1—C9—O4	−25.1 (9)	C6A—N1A—C9A—O4A	−16.6 (9)
C8—N1—C9—O4	−168.6 (5)	C8A—N1A—C9A—O4A	−166.2 (5)
C6—N1—C9—C10	157.1 (5)	C6A—N1A—C9A—C10A	165.1 (5)
C8—N1—C9—C10	13.7 (7)	C8A—N1A—C9A—C10A	15.6 (7)
O4—C9—C10—C11	142.2 (6)	O4A—C9A—C10A—C11A	139.5 (6)
N1—C9—C10—C11	−40.1 (7)	N1A—C9A—C10A—C11A	−42.3 (8)
C12—O1—C11—C18	−66.6 (6)	C12A—O1A—C11A—C10A	170.5 (5)
C12—O1—C11—C10	172.2 (5)	C12A—O1A—C11A—C18A	−69.4 (6)
C9—C10—C11—O1	132.2 (5)	C9A—C10A—C11A—O1A	131.2 (5)
C9—C10—C11—C18	8.7 (7)	C9A—C10A—C11A—C18A	8.3 (7)
C11—O1—C12—C13	89.5 (6)	C11A—O1A—C12A—C13A	89.7 (6)
O1—C12—C13—C14	−66.7 (8)	O1A—C12A—C13A—C14A	−63.5 (8)
C12—C13—C14—C15	177.8 (5)	C12A—C13A—C14A—C15A	175.9 (6)
C12—C13—C14—C19	−3.1 (9)	C12A—C13A—C14A—C19A	−4.0 (10)
C13—C14—C15—N2	−130.1 (6)	C13A—C14A—C15A—N2A	−125.7 (6)
C19—C14—C15—N2	50.7 (7)	C19A—C14A—C15A—N2A	54.2 (7)
C16—N2—C15—C14	78.5 (6)	C16A—N2A—C15A—C14A	75.3 (6)
C21—N2—C15—C14	−44.5 (6)	C21A—N2A—C15A—C14A	−47.4 (6)
C15—N2—C16—C17	−141.4 (5)	C15A—N2A—C16A—C17A	−143.6 (5)
C21—N2—C16—C17	−14.7 (6)	C21A—N2A—C16A—C17A	−17.6 (6)
N2—C16—C17—C7	36.9 (6)	N2A—C16A—C17A—C7A	37.1 (6)
C5—C7—C17—C16	−168.2 (5)	C5A—C7A—C17A—C16A	−167.4 (5)
C21—C7—C17—C16	−44.4 (6)	C21A—C7A—C17A—C16A	−41.8 (5)
C8—C7—C17—C16	78.3 (6)	C8A—C7A—C17A—C16A	79.1 (5)
O1—C11—C18—C19	55.9 (7)	N1A—C8A—C18A—C19A	155.6 (4)
C10—C11—C18—C19	173.1 (5)	C7A—C8A—C18A—C19A	39.4 (7)
O1—C11—C18—C8	−73.9 (6)	N1A—C8A—C18A—C11A	−72.1 (5)
C10—C11—C18—C8	43.4 (6)	C7A—C8A—C18A—C11A	171.7 (5)
N1—C8—C18—C19	158.2 (5)	O1A—C11A—C18A—C8A	−71.9 (6)
C7—C8—C18—C19	42.7 (7)	C10A—C11A—C18A—C8A	46.2 (6)
N1—C8—C18—C11	−69.0 (6)	O1A—C11A—C18A—C19A	57.2 (7)
C7—C8—C18—C11	175.5 (5)	C10A—C11A—C18A—C19A	175.3 (5)
C11—C18—C19—C20	171.1 (5)	C13A—C14A—C19A—C20A	176.4 (6)
C8—C18—C19—C20	−61.5 (6)	C15A—C14A—C19A—C20A	−3.5 (7)
C11—C18—C19—C14	−68.4 (7)	C13A—C14A—C19A—C18A	57.9 (8)
C8—C18—C19—C14	59.0 (7)	C15A—C14A—C19A—C18A	−122.0 (6)
C13—C14—C19—C18	60.9 (8)	C8A—C18A—C19A—C14A	60.3 (7)
C15—C14—C19—C18	−119.9 (6)	C11A—C18A—C19A—C14A	−65.7 (7)
C13—C14—C19—C20	−178.7 (6)	C8A—C18A—C19A—C20A	−60.2 (6)
C15—C14—C19—C20	0.5 (7)	C11A—C18A—C19A—C20A	173.8 (5)
C18—C19—C20—C21	66.0 (6)	C14A—C19A—C20A—C21A	−54.3 (6)
C14—C19—C20—C21	−57.4 (6)	C18A—C19A—C20A—C21A	69.0 (6)
C19—C20—C21—N2	63.3 (6)	C19A—C20A—C21A—N2A	61.1 (6)
C19—C20—C21—C7	−53.6 (6)	C19A—C20A—C21A—C7A	−57.5 (6)
C15—N2—C21—C20	−10.4 (6)	C16A—N2A—C21A—C20A	−133.9 (5)
C16—N2—C21—C20	−135.8 (5)	C15A—N2A—C21A—C20A	−8.7 (7)
C15—N2—C21—C7	113.0 (5)	C16A—N2A—C21A—C7A	−8.6 (6)
C16—N2—C21—C7	−12.4 (6)	C15A—N2A—C21A—C7A	116.6 (5)
C5—C7—C21—C20	−84.4 (6)	C5A—C7A—C21A—C20A	−84.3 (6)
C17—C7—C21—C20	154.3 (5)	C17A—C7A—C21A—C20A	152.9 (5)
C8—C7—C21—C20	35.0 (7)	C8A—C7A—C21A—C20A	33.8 (7)
C5—C7—C21—N2	155.7 (5)	C5A—C7A—C21A—N2A	153.5 (5)
C17—C7—C21—N2	34.5 (6)	C17A—C7A—C21A—N2A	30.6 (5)
C8—C7—C21—N2	−84.9 (6)	C8A—C7A—C21A—N2A	−88.4 (5)
O5—C24—C25—C30	176.1 (6)	O5A—C24A—C25A—C26A	172.8 (6)
O6—C24—C25—C30	−4.0 (8)	O6A—C24A—C25A—C26A	−5.4 (8)
O5—C24—C25—C26	−3.5 (8)	O5A—C24A—C25A—C30A	−4.4 (8)
O6—C24—C25—C26	176.4 (5)	O6A—C24A—C25A—C30A	177.5 (6)
C30—C25—C26—C27	2.7 (8)	C30A—C25A—C26A—C27A	0.9 (9)
C24—C25—C26—C27	−177.6 (5)	C24A—C25A—C26A—C27A	−176.3 (5)
C25—C26—C27—C28	−1.5 (9)	C25A—C26A—C27A—C28A	−0.1 (9)
C26—C27—C28—C29	−0.3 (9)	C26A—C27A—C28A—C29A	−1.8 (9)
C27—C28—C29—C30	0.9 (9)	C27A—C28A—C29A—C30A	2.8 (9)
C26—C25—C30—C29	−2.1 (9)	C28A—C29A—C30A—C25A	−1.9 (9)
C24—C25—C30—C29	178.3 (5)	C26A—C25A—C30A—C29A	0.1 (9)
C28—C29—C30—C25	0.3 (9)	C24A—C25A—C30A—C29A	177.3 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O5	0.93	1.80	2.693 (6)	160
N2A—H2A···O5A	0.93	1.68	2.595 (6)	168
O1W—H11W···O5^i	0.88	1.88	2.748 (6)	169
O1W—H12W···O6W	0.88	1.98	2.857 (6)	176
O2W—H21W···O5A^ii	0.88	1.87	2.752 (6)	179
O2W—H22W···O1W^iii	0.88	1.88	2.764 (6)	179
O3W—H31W···O2W	0.88	1.98	2.864 (6)	179
O3W—H32W···O4W	0.88	1.94	2.822 (6)	179
O4W—H41W···O6	0.88	1.92	2.784 (6)	165
O4W—H42W···O6A^iv	0.88	1.93	2.813 (6)	179
O5W—H51W···O4^v	0.88	2.19	2.915 (6)	140
O5W—H52W···O6W	0.88	1.99	2.872 (6)	178
O6W—H61W···O6A^iv	0.88	1.93	2.798 (6)	168
O6W—H62W···O6	0.88	1.83	2.707 (6)	179
C28—H28···O4A^vi	0.95	2.48	3.118 (7)	125

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