Cilansetron hydro­chloride monohydrate, modification A (monoclinic)

The absolute configuration of the monoclinic form of the title compound, (-)-5,6,9,10-tetra­hydro-10-[(2-methyl-1H-imid­a­zol-1-yl)­methyl]-4H-pyrido­[3,2,1-jk]­carbazol-11(8H)-one mono­hydro­chloride monohydrate, C₂₀H₂₂N₃O⁺·Cl^-·H₂O, was established as R at the asymmetric carbon adjacent to the carbonyl function. This form [cf. the orthorhombic form; Jones et al. (2003). Acta Cryst. E59, o41-o43] involves two independent formula units with different ring conformations of the six-membered N-heterocycle, and somewhat different orientations of the imidazole ring. Each independent formula unit forms a helical hydrogen-bonded chain of alternating water and chloride residues; the cations are hydrogen bonded laterally to the chlorides.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.046
• wR factor = 0.103
• Data-to-parameter ratio = 10.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_353  Alert C Long    N-H Bond (0.87A)   N3'    -   H3'    =       1.03 Ang.

PLAT_353  Alert C Long    N-H Bond (0.87A)   N23'   -   H23'   =       1.03 Ang.

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.00
         From the CIF: _reflns_number_total               5297
         Count of symmetry unique reflns         3545
         Completeness (_total/calc)            149.42%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      1752
         Fraction of Friedel pairs measured     0.494
         Are heavy atom types Z>Si present          yes
          WARNING: Large fraction of Friedel related reflns may
                   be needed to determine absolute structure


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

---

Computing details

Data collection: XSCANS (Fait, 1991); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

R-(-)-5,6,9,10-tetrahydro-10- [(2-methyl-1H-imidazol-1-yl)-methyl]-4H-pyrido[3,2,1-jk]-carbazol-11(8H)-one monohydrochloride monohydrate

Crystal data

C20H22N3O^+·Cl^−·H2O	F(000) = 792
Mr = 373.87	Dx = 1.342 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 15.403 (3) Å	Cell parameters from 62 reflections
b = 7.3835 (14) Å	θ = 4–12.5°
c = 16.281 (3) Å	µ = 0.23 mm^−1
β = 92.438 (12)°	T = 173 K
V = 1849.9 (6) Å^3	Lath, colourless
Z = 4	0.7 × 0.3 × 0.1 mm

Data collection

Siemens P4 diffractometer	Rint = 0.041
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 3.0°
Graphite monochromator	h = −18→18
ω scans	k = −8→5
5792 measured reflections	l = −19→14
5297 independent reflections	3 standard reflections every 247 reflections
3621 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0468P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.90	(Δ/σ)max = 0.001
5297 reflections	Δρmax = 0.26 e Å^−3
505 parameters	Δρmin = −0.26 e Å^−3
39 restraints	Absolute structure: Flack (1983), 1772 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.07 (8)

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)
Cl1	0.39395 (8)	0.95511 (19)	0.53975 (8)	0.0383 (4)
Cl2	0.40424 (8)	0.52389 (17)	0.04001 (7)	0.0334 (4)
C1	1.0234 (3)	0.5638 (7)	0.1427 (3)	0.0265 (12)
H1	0.9929	0.5656	0.1922	0.032*
C2	1.1142 (3)	0.5571 (8)	0.1441 (3)	0.0308 (13)
H2	1.1458	0.5544	0.1955	0.037*
C3	1.1594 (3)	0.5542 (7)	0.0718 (3)	0.0278 (12)
H3	1.2211	0.5496	0.0754	0.033*
C3A	1.1175 (3)	0.5579 (7)	−0.0050 (3)	0.0251 (11)
C4	1.1575 (3)	0.5488 (8)	−0.0872 (3)	0.0342 (13)
H4A	1.1717	0.4213	−0.0998	0.041*	0.781 (14)
H4B	1.2123	0.6189	−0.0853	0.041*	0.781 (14)
H4A*	1.1803	0.6702	−0.1004	0.041*	0.219 (14)
H4B*	1.2075	0.4647	−0.0831	0.041*	0.219 (14)
C5	1.0969 (4)	0.6236 (13)	−0.1549 (4)	0.036 (2)	0.781 (14)
H5A	1.0954	0.7571	−0.1496	0.043*	0.781 (14)
H5B	1.1217	0.5952	−0.2085	0.043*	0.781 (14)
C6	1.0052 (3)	0.5549 (8)	−0.1563 (3)	0.0307 (12)
H6A	0.9681	0.6302	−0.1940	0.037*	0.781 (14)
H6B	1.0033	0.4287	−0.1769	0.037*	0.781 (14)
H6A*	1.0011	0.6769	−0.1815	0.037*	0.219 (14)
H6B*	0.9690	0.4713	−0.1908	0.037*	0.219 (14)
C5*	1.1000 (9)	0.491 (4)	−0.1544 (11)	0.028 (6)*	0.219 (14)
H5A*	1.0996	0.3568	−0.1547	0.033*	0.219 (14)
H5B*	1.1255	0.5306	−0.2061	0.033*	0.219 (14)
N7	0.9720 (2)	0.5615 (6)	−0.0736 (2)	0.0228 (9)
C7A	0.8894 (3)	0.5575 (7)	−0.0490 (3)	0.0215 (11)
C8	0.8096 (3)	0.5503 (7)	−0.1048 (3)	0.0222 (11)
H8A	0.8028	0.4272	−0.1283	0.027*
H8B	0.8153	0.6369	−0.1507	0.027*
C9	0.7297 (3)	0.5980 (7)	−0.0569 (2)	0.0286 (12)
H9A	0.6770	0.5628	−0.0899	0.034*
H9B	0.7279	0.7309	−0.0490	0.034*
C10	0.7281 (3)	0.5058 (6)	0.0269 (3)	0.0243 (12)
H10	0.7268	0.3720	0.0174	0.029*
C11	0.8102 (3)	0.5490 (7)	0.0808 (3)	0.0239 (11)
C11A	0.8896 (3)	0.5630 (7)	0.0363 (3)	0.0194 (10)
C11B	0.9793 (3)	0.5676 (6)	0.0660 (3)	0.0197 (11)
C11C	1.0273 (3)	0.5641 (7)	−0.0044 (3)	0.0226 (11)
C12	0.6453 (3)	0.5569 (8)	0.0699 (3)	0.0319 (13)
H12A	0.6471	0.6879	0.0827	0.038*
H12B	0.5948	0.5355	0.0316	0.038*
O1	0.80890 (18)	0.5650 (5)	0.15573 (19)	0.0307 (9)
N1'	0.6325 (2)	0.4567 (6)	0.1457 (2)	0.0273 (9)
C2'	0.6319 (3)	0.5245 (7)	0.2216 (3)	0.0282 (12)
N3'	0.6219 (2)	0.3900 (6)	0.2738 (2)	0.0334 (9)
H3'	0.618 (2)	0.411 (5)	0.336 (2)	0.024 (11)*
C4'	0.6169 (3)	0.2295 (8)	0.2318 (3)	0.0375 (13)
H4'	0.6103	0.1123	0.2547	0.045*
C5'	0.6232 (3)	0.2704 (7)	0.1513 (3)	0.0332 (12)
H5'	0.6216	0.1870	0.1068	0.040*
C13	0.6420 (3)	0.7176 (7)	0.2439 (3)	0.0355 (12)
H13A	0.6350	0.7322	0.3031	0.043*
H13B	0.5977	0.7893	0.2136	0.043*
H13C	0.6999	0.7594	0.2299	0.043*
C21	−0.0212 (3)	0.3905 (7)	0.3514 (3)	0.0248 (11)
H21	0.0090	0.3892	0.3017	0.030*
C22	−0.1111 (3)	0.3970 (7)	0.3504 (3)	0.0268 (12)
H22	−0.1425	0.3993	0.2989	0.032*
C23	−0.1574 (3)	0.4005 (7)	0.4227 (3)	0.0286 (12)
H23	−0.2190	0.4075	0.4192	0.034*
C23A	−0.1142 (3)	0.3938 (7)	0.5000 (3)	0.0263 (11)
C24	−0.1551 (3)	0.4028 (8)	0.5825 (3)	0.0330 (13)
H24A	−0.2100	0.3331	0.5802	0.040*	0.838 (12)
H24B	−0.1690	0.5303	0.5954	0.040*	0.838 (12)
H24C	−0.2044	0.4889	0.5787	0.040*	0.162 (12)
H24D	−0.1788	0.2820	0.5954	0.040*	0.162 (12)
C25	−0.0937 (3)	0.3256 (10)	0.6503 (3)	0.0272 (18)	0.838 (12)
H25A	−0.1176	0.3550	0.7042	0.033*	0.838 (12)
H25B	−0.0931	0.1920	0.6451	0.033*	0.838 (12)
C26	−0.0018 (3)	0.3927 (8)	0.6500 (3)	0.0282 (12)
H26A	0.0005	0.5195	0.6696	0.034*	0.838 (12)
H26B	0.0352	0.3184	0.6881	0.034*	0.838 (12)
H26C	0.0354	0.4752	0.6840	0.034*	0.162 (12)
H26D	0.0016	0.2709	0.6755	0.034*	0.162 (12)
C25*	−0.0951 (10)	0.459 (5)	0.6501 (14)	0.025 (7)*	0.162 (12)
H25C	−0.1199	0.4191	0.7022	0.030*	0.162 (12)
H25D	−0.0938	0.5931	0.6509	0.030*	0.162 (12)
N27	0.0315 (2)	0.3830 (6)	0.5676 (2)	0.0230 (9)
C27A	0.1149 (3)	0.3862 (7)	0.5432 (3)	0.0213 (10)
C28	0.1939 (3)	0.3889 (8)	0.5977 (3)	0.0276 (12)
H28A	0.2074	0.2647	0.6172	0.033*
H28B	0.1841	0.4658	0.6462	0.033*
C29	0.2703 (3)	0.4633 (6)	0.5511 (2)	0.0261 (11)
H29A	0.3249	0.4393	0.5836	0.031*
H29B	0.2639	0.5962	0.5456	0.031*
C30	0.2775 (3)	0.3805 (7)	0.4651 (2)	0.0231 (10)
H30	0.2908	0.2488	0.4725	0.028*
C31	0.1930 (3)	0.3946 (7)	0.4136 (3)	0.0211 (11)
C31A	0.1150 (3)	0.3879 (7)	0.4577 (2)	0.0205 (10)
C31B	0.0239 (3)	0.3858 (7)	0.4282 (3)	0.0226 (11)
C31C	−0.0243 (3)	0.3864 (7)	0.4986 (3)	0.0225 (11)
C32	0.3547 (3)	0.4666 (7)	0.4258 (3)	0.0253 (11)
H32A	0.3428	0.5974	0.4181	0.030*
H32B	0.4061	0.4550	0.4640	0.030*
O2	0.19298 (19)	0.4058 (5)	0.33775 (18)	0.0313 (9)
N21'	0.3759 (2)	0.3878 (6)	0.3457 (2)	0.0243 (8)
C22'	0.3711 (3)	0.4736 (7)	0.2729 (3)	0.0270 (12)
N23'	0.3923 (2)	0.3540 (6)	0.2159 (2)	0.0295 (9)
H23'	0.394 (3)	0.393 (7)	0.155 (2)	0.072 (18)*
C24'	0.4092 (3)	0.1918 (7)	0.2511 (3)	0.0328 (12)
H24'	0.4253	0.0844	0.2235	0.039*
C25'	0.3988 (3)	0.2096 (7)	0.3333 (3)	0.0305 (11)
H25'	0.4059	0.1178	0.3739	0.037*
C33	0.3473 (3)	0.6649 (7)	0.2586 (3)	0.0344 (12)
H33A	0.3454	0.6900	0.1994	0.041*
H33B	0.3906	0.7434	0.2864	0.041*
H33C	0.2900	0.6883	0.2804	0.041*
O1W	0.5055 (2)	0.8102 (6)	0.3947 (2)	0.0503 (10)
H1A	0.543 (3)	0.719 (6)	0.410 (3)	0.065 (19)*
H1B	0.473 (3)	0.864 (6)	0.433 (2)	0.044 (15)*
O2W	0.4839 (2)	0.8951 (5)	0.1126 (2)	0.0410 (9)
H2A	0.516 (3)	0.918 (8)	0.069 (2)	0.08 (2)*
H2B	0.458 (3)	0.797 (6)	0.089 (3)	0.066 (19)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0332 (7)	0.0481 (10)	0.0341 (8)	0.0018 (6)	0.0075 (6)	0.0068 (6)
Cl2	0.0314 (7)	0.0420 (10)	0.0270 (7)	−0.0044 (6)	0.0042 (5)	0.0046 (6)
C1	0.034 (3)	0.025 (3)	0.020 (3)	−0.003 (2)	−0.001 (2)	0.003 (2)
C2	0.030 (3)	0.035 (3)	0.027 (3)	0.003 (3)	−0.006 (2)	0.003 (3)
C3	0.017 (2)	0.030 (3)	0.037 (3)	0.002 (2)	−0.003 (2)	−0.006 (3)
C3A	0.025 (2)	0.025 (3)	0.026 (3)	0.001 (2)	0.007 (2)	0.004 (2)
C4	0.031 (3)	0.040 (4)	0.032 (3)	0.003 (3)	0.014 (2)	−0.003 (3)
C5	0.044 (4)	0.045 (6)	0.021 (3)	−0.020 (4)	0.014 (3)	−0.002 (3)
C6	0.041 (3)	0.032 (3)	0.020 (3)	−0.002 (3)	0.007 (2)	−0.002 (3)
N7	0.029 (2)	0.022 (3)	0.017 (2)	−0.0008 (19)	0.0016 (16)	−0.0002 (18)
C7A	0.024 (2)	0.022 (3)	0.018 (2)	0.002 (2)	0.0014 (18)	−0.004 (2)
C8	0.024 (2)	0.022 (3)	0.020 (2)	0.002 (2)	−0.0033 (19)	0.002 (2)
C9	0.024 (2)	0.036 (3)	0.025 (2)	0.003 (2)	−0.010 (2)	0.003 (2)
C10	0.023 (2)	0.027 (3)	0.022 (2)	−0.001 (2)	−0.0048 (17)	−0.005 (2)
C11	0.021 (2)	0.026 (3)	0.024 (3)	0.002 (2)	−0.0035 (19)	0.001 (2)
C11A	0.020 (2)	0.018 (3)	0.020 (2)	0.006 (2)	0.0014 (18)	−0.003 (2)
C11B	0.027 (2)	0.015 (3)	0.017 (2)	−0.002 (2)	0.0019 (19)	−0.001 (2)
C11C	0.031 (3)	0.016 (3)	0.021 (2)	−0.002 (2)	0.001 (2)	0.001 (2)
C12	0.024 (2)	0.047 (4)	0.025 (3)	0.006 (3)	−0.001 (2)	−0.004 (2)
O1	0.0235 (16)	0.049 (3)	0.0193 (19)	0.0032 (17)	0.0007 (14)	0.0023 (17)
N1'	0.0222 (18)	0.034 (3)	0.027 (2)	−0.0027 (18)	0.0040 (15)	−0.0067 (19)
C2'	0.022 (2)	0.035 (3)	0.028 (3)	0.006 (2)	0.002 (2)	−0.002 (3)
N3'	0.032 (2)	0.043 (3)	0.025 (2)	−0.002 (2)	0.0066 (17)	0.002 (2)
C4'	0.033 (3)	0.028 (3)	0.052 (3)	−0.004 (2)	0.008 (2)	0.001 (3)
C5'	0.028 (2)	0.028 (3)	0.044 (3)	−0.008 (2)	0.009 (2)	−0.012 (2)
C13	0.036 (3)	0.037 (3)	0.033 (3)	0.001 (3)	0.001 (2)	−0.010 (2)
C21	0.029 (3)	0.023 (3)	0.022 (3)	0.000 (2)	−0.002 (2)	0.001 (2)
C22	0.032 (3)	0.023 (3)	0.025 (3)	−0.007 (2)	−0.005 (2)	0.005 (2)
C23	0.027 (3)	0.026 (3)	0.033 (3)	−0.002 (2)	−0.001 (2)	0.008 (3)
C23A	0.030 (3)	0.017 (3)	0.031 (3)	−0.003 (2)	0.006 (2)	0.004 (3)
C24	0.031 (3)	0.029 (3)	0.040 (3)	0.004 (3)	0.011 (2)	0.010 (3)
C25	0.032 (3)	0.027 (4)	0.023 (3)	−0.007 (3)	0.009 (2)	−0.002 (3)
C26	0.035 (3)	0.032 (3)	0.017 (2)	0.000 (3)	0.006 (2)	0.000 (2)
N27	0.029 (2)	0.023 (2)	0.017 (2)	−0.002 (2)	0.0021 (16)	0.000 (2)
C27A	0.019 (2)	0.020 (3)	0.025 (2)	−0.004 (2)	0.0003 (18)	0.000 (2)
C28	0.030 (3)	0.038 (3)	0.015 (2)	−0.002 (3)	0.0001 (19)	−0.003 (2)
C29	0.026 (2)	0.031 (3)	0.020 (2)	−0.001 (2)	−0.0048 (18)	0.001 (2)
C30	0.026 (2)	0.026 (3)	0.017 (2)	0.000 (2)	0.0009 (17)	−0.003 (2)
C31	0.025 (2)	0.018 (3)	0.020 (2)	0.004 (2)	−0.0002 (19)	0.001 (2)
C31A	0.024 (2)	0.022 (3)	0.015 (2)	−0.001 (2)	−0.0019 (18)	0.004 (2)
C31B	0.028 (2)	0.014 (3)	0.026 (3)	0.003 (2)	0.002 (2)	0.003 (2)
C31C	0.024 (2)	0.025 (3)	0.019 (2)	−0.001 (2)	−0.0004 (19)	0.001 (2)
C32	0.023 (2)	0.032 (3)	0.021 (2)	0.000 (2)	0.0040 (19)	−0.005 (2)
O2	0.0292 (18)	0.049 (3)	0.0157 (18)	−0.0008 (18)	0.0013 (14)	0.0007 (17)
N21'	0.0219 (18)	0.027 (2)	0.025 (2)	−0.0008 (19)	0.0020 (15)	0.001 (2)
C22'	0.025 (2)	0.035 (3)	0.021 (3)	−0.003 (2)	0.004 (2)	0.003 (2)
N23'	0.030 (2)	0.036 (3)	0.023 (2)	−0.0025 (19)	0.0053 (16)	0.000 (2)
C24'	0.037 (3)	0.033 (3)	0.028 (3)	0.003 (2)	0.003 (2)	−0.004 (2)
C25'	0.029 (2)	0.031 (3)	0.033 (3)	0.004 (2)	0.006 (2)	0.004 (2)
C33	0.035 (3)	0.041 (4)	0.027 (3)	−0.004 (2)	0.004 (2)	0.009 (2)
O1W	0.049 (2)	0.060 (3)	0.043 (2)	0.007 (2)	0.0089 (19)	−0.005 (2)
O2W	0.045 (2)	0.039 (2)	0.040 (2)	−0.0051 (19)	0.0112 (16)	−0.0030 (19)

Geometric parameters (Å, º)

C1—C11B	1.396 (6)	C21—H21	0.9500
C1—C2	1.398 (6)	C22—C23	1.402 (7)
C1—H1	0.9500	C22—H22	0.9500
C2—C3	1.394 (6)	C23—C23A	1.399 (6)
C2—H2	0.9500	C23—H23	0.9500
C3—C3A	1.383 (6)	C23A—C31C	1.387 (6)
C3—H3	0.9500	C23A—C24	1.508 (6)
C3A—C11C	1.390 (6)	C24—C25*	1.467 (14)
C3A—C4	1.499 (6)	C24—C25	1.533 (7)
C4—C5*	1.442 (13)	C24—H24A	0.9900
C4—C5	1.518 (7)	C24—H24B	0.9900
C4—H4A	0.9900	C24—H24C	0.9900
C4—H4B	0.9900	C24—H24D	0.9900
C4—H4A*	0.9900	C25—C26	1.499 (6)
C4—H4B*	0.9900	C25—H25A	0.9900
C5—C6	1.500 (7)	C25—H25B	0.9900
C5—H5A	0.9900	C26—N27	1.459 (5)
C5—H5B	0.9900	C26—C25*	1.517 (15)
C6—N7	1.462 (5)	C26—H26A	0.9900
C6—C5*	1.534 (13)	C26—H26B	0.9900
C6—H6A	0.9900	C26—H26C	0.9900
C6—H6B	0.9900	C26—H26D	0.9900
C6—H6A*	0.9900	C25*—H25C	0.9900
C6—H6B*	0.9900	C25*—H25D	0.9900
C5*—H5A*	0.9900	N27—C27A	1.360 (5)
C5*—H5B*	0.9900	N27—C31C	1.384 (5)
N7—C7A	1.349 (5)	C27A—C31A	1.392 (6)
N7—C11C	1.384 (5)	C27A—C28	1.475 (6)
C7A—C11A	1.391 (5)	C28—C29	1.530 (6)
C7A—C8	1.498 (6)	C28—H28A	0.9900
C8—C9	1.524 (6)	C28—H28B	0.9900
C8—H8A	0.9900	C29—C30	1.536 (6)
C8—H8B	0.9900	C29—H29A	0.9900
C9—C10	1.527 (6)	C29—H29B	0.9900
C9—H9A	0.9900	C30—C32	1.513 (6)
C9—H9B	0.9900	C30—C31	1.522 (5)
C10—C12	1.528 (6)	C30—H30	1.0000
C10—C11	1.542 (6)	C31—O2	1.238 (5)
C10—H10	1.0000	C31—C31A	1.426 (6)
C11—O1	1.226 (5)	C31A—C31B	1.464 (6)
C11—C11A	1.451 (6)	C31B—C31C	1.392 (6)
C11A—C11B	1.444 (6)	C32—N21'	1.477 (5)
C11B—C11C	1.391 (6)	C32—H32A	0.9900
C12—N1'	1.459 (6)	C32—H32B	0.9900
C12—H12A	0.9900	N21'—C22'	1.343 (6)
C12—H12B	0.9900	N21'—C25'	1.379 (6)
N1'—C2'	1.333 (6)	C22'—N23'	1.332 (6)
N1'—C5'	1.386 (6)	C22'—C33	1.475 (7)
C2'—N3'	1.321 (6)	N23'—C24'	1.348 (6)
C2'—C13	1.478 (7)	N23'—H23'	1.03 (3)
N3'—C4'	1.369 (6)	C24'—C25'	1.360 (6)
N3'—H3'	1.02 (3)	C24'—H24'	0.9500
C4'—C5'	1.352 (6)	C25'—H25'	0.9500
C4'—H4'	0.9500	C33—H33A	0.9800
C5'—H5'	0.9500	C33—H33B	0.9800
C13—H13A	0.9800	C33—H33C	0.9800
C13—H13B	0.9800	O1W—H1A	0.92 (3)
C13—H13C	0.9800	O1W—H1B	0.91 (3)
C21—C22	1.385 (6)	O2W—H2A	0.90 (3)
C21—C31B	1.405 (6)	O2W—H2B	0.91 (3)
C11B—C1—C2	117.7 (4)	C22—C21—H21	121.1
C11B—C1—H1	121.2	C31B—C21—H21	121.1
C2—C1—H1	121.2	C21—C22—C23	122.3 (5)
C3—C2—C1	121.5 (4)	C21—C22—H22	118.8
C3—C2—H2	119.3	C23—C22—H22	118.8
C1—C2—H2	119.3	C23A—C23—C22	121.0 (4)
C3A—C3—C2	122.2 (4)	C23A—C23—H23	119.5
C3A—C3—H3	118.9	C22—C23—H23	119.5
C2—C3—H3	118.9	C31C—C23A—C23	115.0 (4)
C3—C3A—C11C	115.0 (4)	C31C—C23A—C24	118.1 (4)
C3—C3A—C4	127.8 (4)	C23—C23A—C24	126.7 (4)
C11C—C3A—C4	117.2 (4)	C25*—C24—C23A	114.0 (11)
C5*—C4—C3A	115.3 (9)	C23A—C24—C25	110.9 (4)
C3A—C4—C5	111.6 (4)	C23A—C24—H24A	109.5
C3A—C4—H4A	109.3	C25—C24—H24A	109.5
C5—C4—H4A	109.3	C23A—C24—H24B	109.5
C3A—C4—H4B	109.3	C25—C24—H24B	109.5
C5—C4—H4B	109.3	H24A—C24—H24B	108.1
H4A—C4—H4B	108.0	C25*—C24—H24C	108.8
C5*—C4—H4A*	108.4	C23A—C24—H24C	108.8
C3A—C4—H4A*	108.4	C25*—C24—H24D	108.8
C5*—C4—H4B*	108.4	C23A—C24—H24D	108.8
C3A—C4—H4B*	108.4	H24C—C24—H24D	107.7
H4A*—C4—H4B*	107.5	C26—C25—C24	115.3 (5)
C6—C5—C4	116.0 (5)	C26—C25—H25A	108.4
C6—C5—H5A	108.3	C24—C25—H25A	108.4
C4—C5—H5A	108.3	C26—C25—H25B	108.4
C6—C5—H5B	108.3	C24—C25—H25B	108.4
C4—C5—H5B	108.3	H25A—C25—H25B	107.5
H5A—C5—H5B	107.4	N27—C26—C25	110.8 (4)
N7—C6—C5	109.9 (4)	N27—C26—C25*	112.7 (10)
N7—C6—C5*	111.2 (8)	N27—C26—H26A	109.5
N7—C6—H6A	109.7	C25—C26—H26A	109.5
C5—C6—H6A	109.7	N27—C26—H26B	109.5
N7—C6—H6B	109.7	C25—C26—H26B	109.5
C5—C6—H6B	109.7	H26A—C26—H26B	108.1
H6A—C6—H6B	108.2	N27—C26—H26C	109.0
N7—C6—H6A*	109.4	C25*—C26—H26C	109.0
C5*—C6—H6A*	109.4	N27—C26—H26D	109.0
N7—C6—H6B*	109.4	C25*—C26—H26D	109.0
C5*—C6—H6B*	109.4	H26C—C26—H26D	107.8
H6A*—C6—H6B*	108.0	C24—C25*—C26	118.3 (13)
C4—C5*—C6	118.6 (12)	C24—C25*—H25C	107.7
C4—C5*—H5A*	107.7	C26—C25*—H25C	107.7
C6—C5*—H5A*	107.7	C24—C25*—H25D	107.7
C4—C5*—H5B*	107.7	C26—C25*—H25D	107.7
C6—C5*—H5B*	107.7	H25C—C25*—H25D	107.1
H5A*—C5*—H5B*	107.1	C27A—N27—C31C	108.9 (4)
C7A—N7—C11C	108.4 (4)	C27A—N27—C26	129.8 (4)
C7A—N7—C6	130.0 (4)	C31C—N27—C26	121.0 (4)
C11C—N7—C6	121.5 (4)	N27—C27A—C31A	109.5 (4)
N7—C7A—C11A	109.5 (4)	N27—C27A—C28	126.2 (4)
N7—C7A—C8	125.5 (4)	C31A—C27A—C28	124.3 (4)
C11A—C7A—C8	125.0 (4)	C27A—C28—C29	109.9 (4)
C7A—C8—C9	110.0 (3)	C27A—C28—H28A	109.7
C7A—C8—H8A	109.7	C29—C28—H28A	109.7
C9—C8—H8A	109.7	C27A—C28—H28B	109.7
C7A—C8—H8B	109.7	C29—C28—H28B	109.7
C9—C8—H8B	109.7	H28A—C28—H28B	108.2
H8A—C8—H8B	108.2	C28—C29—C30	113.3 (4)
C8—C9—C10	113.5 (4)	C28—C29—H29A	108.9
C8—C9—H9A	108.9	C30—C29—H29A	108.9
C10—C9—H9A	108.9	C28—C29—H29B	108.9
C8—C9—H9B	108.9	C30—C29—H29B	108.9
C10—C9—H9B	108.9	H29A—C29—H29B	107.7
H9A—C9—H9B	107.7	C32—C30—C31	114.0 (4)
C9—C10—C12	110.2 (4)	C32—C30—C29	107.9 (4)
C9—C10—C11	111.9 (4)	C31—C30—C29	112.4 (4)
C12—C10—C11	111.6 (4)	C32—C30—H30	107.4
C9—C10—H10	107.6	C31—C30—H30	107.4
C12—C10—H10	107.6	C29—C30—H30	107.4
C11—C10—H10	107.6	O2—C31—C31A	122.7 (4)
O1—C11—C11A	122.6 (4)	O2—C31—C30	121.2 (4)
O1—C11—C10	122.6 (4)	C31A—C31—C30	116.1 (4)
C11A—C11—C10	114.8 (4)	C27A—C31A—C31	122.8 (4)
C7A—C11A—C11B	107.2 (4)	C27A—C31A—C31B	106.6 (4)
C7A—C11A—C11	122.1 (4)	C31—C31A—C31B	130.7 (4)
C11B—C11A—C11	130.5 (4)	C31C—C31B—C21	118.2 (4)
C11C—C11B—C1	118.7 (4)	C31C—C31B—C31A	105.5 (4)
C11C—C11B—C11A	105.0 (4)	C21—C31B—C31A	136.3 (4)
C1—C11B—C11A	136.2 (4)	N27—C31C—C23A	125.0 (4)
N7—C11C—C3A	125.1 (4)	N27—C31C—C31B	109.5 (4)
N7—C11C—C11B	109.9 (4)	C23A—C31C—C31B	125.6 (4)
C3A—C11C—C11B	125.0 (4)	N21'—C32—C30	114.5 (4)
N1'—C12—C10	114.1 (4)	N21'—C32—H32A	108.6
N1'—C12—H12A	108.7	C30—C32—H32A	108.6
C10—C12—H12A	108.7	N21'—C32—H32B	108.6
N1'—C12—H12B	108.7	C30—C32—H32B	108.6
C10—C12—H12B	108.7	H32A—C32—H32B	107.6
H12A—C12—H12B	107.6	C22'—N21'—C25'	109.0 (4)
C2'—N1'—C5'	107.9 (4)	C22'—N21'—C32	126.0 (4)
C2'—N1'—C12	126.9 (4)	C25'—N21'—C32	124.9 (4)
C5'—N1'—C12	125.2 (4)	N23'—C22'—N21'	107.2 (5)
N3'—C2'—N1'	108.6 (5)	N23'—C22'—C33	126.3 (5)
N3'—C2'—C13	125.5 (5)	N21'—C22'—C33	126.5 (5)
N1'—C2'—C13	125.8 (5)	C22'—N23'—C24'	109.9 (4)
C2'—N3'—C4'	109.6 (4)	C22'—N23'—H23'	120 (3)
C2'—N3'—H3'	122 (2)	C24'—N23'—H23'	130 (3)
C4'—N3'—H3'	128 (2)	N23'—C24'—C25'	107.7 (5)
C5'—C4'—N3'	106.7 (5)	N23'—C24'—H24'	126.1
C5'—C4'—H4'	126.7	C25'—C24'—H24'	126.1
N3'—C4'—H4'	126.7	C24'—C25'—N21'	106.1 (4)
C4'—C5'—N1'	107.2 (4)	C24'—C25'—H25'	127.0
C4'—C5'—H5'	126.4	N21'—C25'—H25'	127.0
N1'—C5'—H5'	126.4	C22'—C33—H33A	109.5
C2'—C13—H13A	109.5	C22'—C33—H33B	109.5
C2'—C13—H13B	109.5	H33A—C33—H33B	109.5
H13A—C13—H13B	109.5	C22'—C33—H33C	109.5
C2'—C13—H13C	109.5	H33A—C33—H33C	109.5
H13A—C13—H13C	109.5	H33B—C33—H33C	109.5
H13B—C13—H13C	109.5	H1A—O1W—H1B	119 (5)
C22—C21—C31B	117.9 (4)	H2A—O2W—H2B	93 (5)
C11B—C1—C2—C3	0.0 (8)	C31B—C21—C22—C23	0.5 (8)
C1—C2—C3—C3A	0.0 (9)	C21—C22—C23—C23A	−1.3 (8)
C2—C3—C3A—C11C	−0.2 (8)	C22—C23—C23A—C31C	0.9 (8)
C2—C3—C3A—C4	−177.6 (5)	C22—C23—C23A—C24	177.8 (5)
C3—C3A—C4—C5*	158.7 (13)	C31C—C23A—C24—C25*	18.1 (16)
C11C—C3A—C4—C5*	−18.7 (14)	C23—C23A—C24—C25*	−158.7 (15)
C3—C3A—C4—C5	−159.2 (6)	C31C—C23A—C24—C25	−23.3 (7)
C11C—C3A—C4—C5	23.4 (8)	C23—C23A—C24—C25	159.9 (5)
C3A—C4—C5—C6	−48.4 (8)	C23A—C24—C25—C26	47.5 (7)
C4—C5—C6—N7	46.9 (8)	C24—C25—C26—N27	−47.9 (7)
C3A—C4—C5*—C6	38 (2)	C23A—C24—C25*—C26	−37 (3)
N7—C6—C5*—C4	−37 (2)	N27—C26—C25*—C24	37 (3)
C5—C6—N7—C7A	161.4 (6)	C25—C26—N27—C27A	−161.7 (5)
C5*—C6—N7—C7A	−158.2 (12)	C25*—C26—N27—C27A	157.1 (15)
C5—C6—N7—C11C	−22.1 (7)	C25—C26—N27—C31C	24.8 (7)
C5*—C6—N7—C11C	18.3 (13)	C25*—C26—N27—C31C	−16.4 (15)
C11C—N7—C7A—C11A	1.8 (6)	C31C—N27—C27A—C31A	−1.2 (6)
C6—N7—C7A—C11A	178.7 (5)	C26—N27—C27A—C31A	−175.3 (5)
C11C—N7—C7A—C8	−178.8 (5)	C31C—N27—C27A—C28	178.3 (5)
C6—N7—C7A—C8	−1.9 (9)	C26—N27—C27A—C28	4.2 (9)
N7—C7A—C8—C9	−164.9 (5)	N27—C27A—C28—C29	−158.5 (5)
C11A—C7A—C8—C9	14.4 (7)	C31A—C27A—C28—C29	21.0 (8)
C7A—C8—C9—C10	−44.3 (6)	C27A—C28—C29—C30	−46.2 (6)
C8—C9—C10—C12	−178.6 (4)	C28—C29—C30—C32	179.4 (4)
C8—C9—C10—C11	56.5 (5)	C28—C29—C30—C31	52.9 (5)
C9—C10—C11—O1	145.9 (5)	C32—C30—C31—O2	27.4 (7)
C12—C10—C11—O1	21.9 (7)	C29—C30—C31—O2	150.5 (5)
C9—C10—C11—C11A	−36.2 (6)	C32—C30—C31—C31A	−154.7 (4)
C12—C10—C11—C11A	−160.2 (4)	C29—C30—C31—C31A	−31.5 (6)
N7—C7A—C11A—C11B	−1.0 (6)	N27—C27A—C31A—C31	178.9 (5)
C8—C7A—C11A—C11B	179.6 (5)	C28—C27A—C31A—C31	−0.7 (9)
N7—C7A—C11A—C11	−176.0 (5)	N27—C27A—C31A—C31B	0.0 (6)
C8—C7A—C11A—C11	4.6 (8)	C28—C27A—C31A—C31B	−179.5 (5)
O1—C11—C11A—C7A	−175.3 (5)	O2—C31—C31A—C27A	−176.1 (5)
C10—C11—C11A—C7A	6.7 (7)	C30—C31—C31A—C27A	6.0 (8)
O1—C11—C11A—C11B	11.0 (9)	O2—C31—C31A—C31B	2.4 (9)
C10—C11—C11A—C11B	−167.0 (5)	C30—C31—C31A—C31B	−175.5 (5)
C2—C1—C11B—C11C	0.2 (7)	C22—C21—C31B—C31C	0.5 (8)
C2—C1—C11B—C11A	175.2 (6)	C22—C21—C31B—C31A	−176.1 (6)
C7A—C11A—C11B—C11C	−0.1 (6)	C27A—C31A—C31B—C31C	1.1 (6)
C11—C11A—C11B—C11C	174.3 (5)	C31—C31A—C31B—C31C	−177.6 (5)
C7A—C11A—C11B—C1	−175.6 (5)	C27A—C31A—C31B—C21	178.0 (6)
C11—C11A—C11B—C1	−1.2 (10)	C31—C31A—C31B—C21	−0.6 (11)
C7A—N7—C11C—C3A	176.1 (5)	C27A—N27—C31C—C23A	−176.6 (5)
C6—N7—C11C—C3A	−1.1 (8)	C26—N27—C31C—C23A	−1.9 (8)
C7A—N7—C11C—C11B	−1.9 (6)	C27A—N27—C31C—C31B	2.0 (6)
C6—N7—C11C—C11B	−179.1 (4)	C26—N27—C31C—C31B	176.7 (5)
C3—C3A—C11C—N7	−177.3 (5)	C23—C23A—C31C—N27	178.5 (5)
C4—C3A—C11C—N7	0.4 (8)	C24—C23A—C31C—N27	1.4 (8)
C3—C3A—C11C—C11B	0.3 (8)	C23—C23A—C31C—C31B	0.2 (8)
C4—C3A—C11C—C11B	178.1 (5)	C24—C23A—C31C—C31B	−177.0 (5)
C1—C11B—C11C—N7	177.6 (4)	C21—C31B—C31C—N27	−179.5 (5)
C11A—C11B—C11C—N7	1.2 (6)	C31A—C31B—C31C—N27	−1.9 (6)
C1—C11B—C11C—C3A	−0.3 (8)	C21—C31B—C31C—C23A	−0.9 (8)
C11A—C11B—C11C—C3A	−176.8 (5)	C31A—C31B—C31C—C23A	176.7 (5)
C9—C10—C12—N1'	172.4 (4)	C31—C30—C32—N21'	−60.3 (6)
C11—C10—C12—N1'	−62.7 (6)	C29—C30—C32—N21'	174.1 (4)
C10—C12—N1'—C2'	115.2 (5)	C30—C32—N21'—C22'	115.1 (5)
C10—C12—N1'—C5'	−61.2 (6)	C30—C32—N21'—C25'	−60.6 (6)
C5'—N1'—C2'—N3'	−0.7 (5)	C25'—N21'—C22'—N23'	−1.3 (5)
C12—N1'—C2'—N3'	−177.5 (4)	C32—N21'—C22'—N23'	−177.6 (4)
C5'—N1'—C2'—C13	178.6 (4)	C25'—N21'—C22'—C33	179.0 (4)
C12—N1'—C2'—C13	1.8 (7)	C32—N21'—C22'—C33	2.7 (7)
N1'—C2'—N3'—C4'	0.9 (5)	N21'—C22'—N23'—C24'	1.1 (5)
C13—C2'—N3'—C4'	−178.4 (4)	C33—C22'—N23'—C24'	−179.2 (4)
C2'—N3'—C4'—C5'	−0.7 (5)	C22'—N23'—C24'—C25'	−0.4 (5)
N3'—C4'—C5'—N1'	0.3 (5)	N23'—C24'—C25'—N21'	−0.4 (5)
C2'—N1'—C5'—C4'	0.2 (5)	C22'—N21'—C25'—C24'	1.1 (5)
C12—N1'—C5'—C4'	177.1 (4)	C32—N21'—C25'—C24'	177.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3′—H3′···Cl1^i	1.02 (3)	2.07 (3)	3.093 (4)	178 (3)
N23′—H23′···Cl2	1.03 (3)	2.12 (3)	3.138 (4)	169 (5)
O2W—H2A···Cl2^ii	0.90 (3)	2.33 (3)	3.227 (4)	171 (5)
O2W—H2B···Cl2	0.91 (3)	2.31 (3)	3.208 (4)	172 (5)
O1W—H1A···Cl1^i	0.92 (3)	2.31 (3)	3.205 (5)	166 (5)
O1W—H1B···Cl1	0.91 (3)	2.27 (3)	3.165 (4)	170 (4)
C23—H23···Cl1^iii	0.95	2.83	3.742 (5)	162
C30—H30···Cl1^iv	1.00	2.88	3.791 (5)	152
C3—H3···Cl2^v	0.95	2.91	3.834 (5)	165
C5′—H5′···Cl2^vi	0.95	2.69	3.616 (5)	165
C2—H2···O2^v	0.95	2.64	3.512 (6)	153
C25—H25B···O2^iii	0.99	2.64	3.465 (7)	141
C13—H13B···O2W	0.98	2.48	3.431 (6)	164
C24′—H24′···O2W^iv	0.95	2.48	3.381 (6)	158
C13—H13A···O1W	0.98	2.61	3.369 (6)	135
C33—H33B···O1W	0.98	2.49	3.398 (6)	153

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