Cilansetron hydro­chloride monohydrate, modification B (orthorhombic)

The absolute configuration of the orthorhombic 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 monoclinic form; Jones et al. (2003). Acta Cryst. E59, o38-o40] also involves two independent formula units with different ring conformations of the six-membered N-heterocycle, and somewhat different orientations of the imidazole ring. Classical hydrogen bonding leads to a helical chain of alternating water and chloride residues, with cations hydrogen bonded laterally to the water molecules.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.058
• wR factor = 0.105
• Data-to-parameter ratio = 13.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



RINTA_01  Alert C The value of Rint is greater than 0.10
          Rint given   0.112

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.12
         From the CIF: _reflns_number_total               6553
         Count of symmetry unique reflns         3745
         Completeness (_total/calc)            174.98%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      2808
         Fraction of Friedel pairs measured     0.750
         Are heavy atom types Z>Si present          yes
          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.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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	Dx = 1.348 Mg m^−3
Mr = 373.87	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 5470 reflections
a = 7.396 (2) Å	θ = 2–25°
b = 16.460 (3) Å	µ = 0.23 mm^−1
c = 30.263 (6) Å	T = 123 K
V = 3684.2 (14) Å^3	Lath, colourless
Z = 8	0.70 × 0.23 × 0.04 mm
F(000) = 1584

Data collection

Stoe-Huber-Siemens area-detector diffractometer	5335 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.112
Graphite monochromator	θmax = 25.1°, θmin = 2.4°
Detector resolution: 8.192 pixels mm^-1	h = −8→8
φ–scan	k = 0→19
61630 measured reflections	l = 0→36
6553 independent reflections

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)] = 0.058	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.105	w = 1/[σ^2(Fo^2) + (0.018P)^2 + 3.9789P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max < 0.001
6553 reflections	Δρmax = 0.36 e Å^−3
500 parameters	Δρmin = −0.27 e Å^−3
15 restraints	Absolute structure: Flack (1983), 2820 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.03 (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)
C1	0.5799 (5)	0.1127 (2)	0.51381 (13)	0.0208 (9)
H1	0.5764	0.0623	0.4986	0.025*
C2	0.5867 (5)	0.1151 (2)	0.55962 (13)	0.0220 (9)
H2	0.5908	0.0656	0.5757	0.026*
C3	0.5877 (5)	0.1892 (2)	0.58271 (13)	0.0245 (9)
H3	0.5894	0.1888	0.6141	0.029*
C3A	0.5862 (5)	0.2629 (2)	0.56062 (13)	0.0214 (9)
C4	0.5962 (5)	0.3469 (2)	0.58063 (13)	0.0271 (9)
H4A	0.7239	0.3604	0.5871	0.033*
H4B	0.5283	0.3477	0.6088	0.033*
C5	0.5173 (6)	0.4106 (3)	0.54923 (14)	0.0333 (11)
H5A	0.3843	0.4038	0.5483	0.040*
H5B	0.5427	0.4652	0.5614	0.040*
C6	0.5887 (5)	0.4070 (2)	0.50259 (14)	0.0255 (9)
H6A	0.5154	0.4427	0.4833	0.031*
H6B	0.7152	0.4267	0.5019	0.031*
N7	0.5811 (4)	0.32330 (18)	0.48615 (10)	0.0211 (7)
C7A	0.5853 (5)	0.2956 (2)	0.44388 (13)	0.0196 (8)
C8	0.5921 (5)	0.3460 (2)	0.40364 (12)	0.0234 (8)
H8A	0.7152	0.3686	0.3999	0.028*
H8B	0.5062	0.3918	0.4064	0.028*
C9	0.5428 (5)	0.2944 (2)	0.36339 (13)	0.0258 (9)
H9A	0.5761	0.3244	0.3362	0.031*
H9B	0.4103	0.2860	0.3629	0.031*
C10	0.6374 (5)	0.2111 (2)	0.36299 (12)	0.0200 (8)
H10	0.7708	0.2208	0.3617	0.024*
C11	0.5978 (5)	0.1635 (2)	0.40515 (12)	0.0204 (8)
O1	0.5855 (4)	0.08844 (15)	0.40521 (9)	0.0254 (6)
C11A	0.5822 (5)	0.2108 (2)	0.44469 (12)	0.0177 (8)
C11B	0.5783 (5)	0.1859 (2)	0.49066 (12)	0.0184 (8)
C11C	0.5796 (5)	0.2582 (2)	0.51502 (12)	0.0188 (8)
C12	0.5820 (6)	0.1668 (2)	0.32048 (12)	0.0275 (9)
H12A	0.4495	0.1586	0.3210	0.033*
H12B	0.6099	0.2025	0.2950	0.033*
C13	0.3995 (5)	−0.0009 (3)	0.32620 (12)	0.0260 (8)
H13A	0.3754	0.0122	0.3572	0.031*
H13B	0.3739	−0.0585	0.3209	0.031*
H13C	0.3220	0.0324	0.3072	0.031*
N1'	0.6692 (4)	0.0878 (2)	0.31312 (11)	0.0231 (8)
C2'	0.5909 (5)	0.0160 (2)	0.31600 (12)	0.0231 (9)
N3'	0.7150 (5)	−0.0401 (2)	0.30683 (11)	0.0287 (8)
H3'	0.689 (7)	−0.092 (2)	0.3064 (18)	0.08 (2)*
C4'	0.8770 (5)	−0.0030 (3)	0.29733 (13)	0.0328 (10)
H4'	0.9872	−0.0292	0.2897	0.039*
C5'	0.8491 (6)	0.0786 (3)	0.30102 (14)	0.0325 (12)
H5'	0.9351	0.1205	0.2963	0.039*
C21	0.7671 (5)	0.1054 (2)	−0.01679 (12)	0.0206 (8)
H21	0.7644	0.0544	−0.0021	0.025*
C22	0.7743 (5)	0.1094 (2)	−0.06242 (12)	0.0243 (9)
H22	0.7764	0.0603	−0.0790	0.029*
C23	0.7786 (5)	0.1839 (2)	−0.08498 (12)	0.0233 (9)
H23	0.7860	0.1842	−0.1163	0.028*
C23A	0.7723 (5)	0.2575 (2)	−0.06235 (11)	0.0204 (8)
C24	0.7767 (5)	0.3422 (2)	−0.08171 (12)	0.0273 (9)
H24A	0.7049	0.3432	−0.1093	0.033*	0.767 (12)
H24B	0.9029	0.3567	−0.0892	0.033*	0.767 (12)
H24C	0.8633	0.3427	−0.1067	0.033*	0.233 (12)
H24D	0.6556	0.3548	−0.0938	0.033*	0.233 (12)
C25	0.6996 (8)	0.4054 (3)	−0.04893 (17)	0.0251 (17)	0.767 (12)
H25A	0.7274	0.4604	−0.0603	0.030*	0.767 (12)
H25B	0.5664	0.3997	−0.0483	0.030*	0.767 (12)
C26	0.7678 (6)	0.3997 (2)	−0.00283 (13)	0.0291 (9)
H26A	0.8940	0.4197	−0.0016	0.035*	0.767 (12)
H26B	0.6932	0.4344	0.0167	0.035*	0.767 (12)
H26C	0.8542	0.4307	0.0157	0.035*	0.233 (12)
H26D	0.6470	0.4248	0.0006	0.035*	0.233 (12)
C25"	0.826 (2)	0.4052 (9)	−0.0514 (4)	0.014 (5)*	0.233 (12)
H25C	0.7782	0.4569	−0.0633	0.017*	0.233 (12)
H25D	0.9596	0.4095	−0.0518	0.017*	0.233 (12)
N27	0.7609 (4)	0.31583 (16)	0.01259 (9)	0.0184 (6)
C27A	0.7618 (5)	0.2865 (2)	0.05449 (11)	0.0188 (8)
C28	0.7631 (5)	0.3363 (2)	0.09559 (11)	0.0208 (8)
H28A	0.6388	0.3546	0.1026	0.025*
H28B	0.8397	0.3850	0.0913	0.025*
C29	0.8375 (5)	0.2850 (2)	0.13354 (13)	0.0211 (9)
H29A	0.8159	0.3140	0.1617	0.025*
H29B	0.9698	0.2793	0.1298	0.025*
C30	0.7533 (5)	0.2000 (2)	0.13663 (11)	0.0183 (7)
H30	0.6221	0.2068	0.1438	0.022*
C31	0.7670 (5)	0.1530 (2)	0.09276 (11)	0.0180 (7)
O2	0.7765 (4)	0.07851 (14)	0.09180 (8)	0.0248 (6)
C31A	0.7633 (5)	0.2021 (2)	0.05346 (11)	0.0168 (8)
C31B	0.7638 (5)	0.1786 (2)	0.00754 (11)	0.0177 (7)
C31C	0.7640 (5)	0.2510 (2)	−0.01673 (11)	0.0189 (8)
C32	0.8427 (5)	0.1569 (2)	0.17555 (12)	0.0202 (8)
H32A	0.9741	0.1529	0.1697	0.024*
H32B	0.8269	0.1908	0.2023	0.024*
C33	1.0553 (5)	−0.0035 (3)	0.16752 (12)	0.0237 (9)
H33A	1.0686	0.0105	0.1362	0.028*
H33B	1.0930	−0.0599	0.1722	0.028*
H33C	1.1309	0.0327	0.1854	0.028*
N21'	0.7736 (4)	0.07546 (17)	0.18488 (9)	0.0180 (7)
C22'	0.8645 (5)	0.0059 (3)	0.18070 (11)	0.0197 (8)
N23'	0.7529 (5)	−0.0544 (2)	0.19179 (10)	0.0239 (7)
H23'	0.785 (6)	−0.106 (2)	0.1950 (14)	0.042 (14)*
C24'	0.5871 (5)	−0.0225 (2)	0.20293 (13)	0.0269 (10)
H24'	0.4835	−0.0523	0.2120	0.032*
C25'	0.5987 (5)	0.0581 (2)	0.19870 (13)	0.0233 (9)
H25'	0.5051	0.0963	0.2041	0.028*
Cl1	0.75471 (13)	0.34232 (6)	0.25214 (3)	0.0264 (2)
Cl2	1.22607 (12)	0.15229 (6)	0.24328 (3)	0.0255 (2)
O1W	1.4041 (5)	0.30365 (19)	0.19926 (11)	0.0353 (7)
H01	1.354 (6)	0.265 (2)	0.2129 (15)	0.057 (18)*
H02	1.501 (5)	0.313 (3)	0.2129 (15)	0.065 (19)*
O2W	1.0985 (4)	0.29336 (18)	0.30276 (10)	0.0296 (7)
H03	0.998 (4)	0.301 (3)	0.2899 (14)	0.044 (15)*
H04	1.154 (6)	0.258 (3)	0.2875 (16)	0.07 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.019 (2)	0.015 (2)	0.029 (2)	0.0009 (16)	−0.0006 (18)	0.0008 (17)
C2	0.020 (2)	0.024 (2)	0.022 (2)	0.0008 (17)	0.0027 (18)	0.0086 (18)
C3	0.022 (2)	0.030 (2)	0.022 (2)	−0.0021 (18)	0.0019 (17)	−0.0021 (18)
C3A	0.016 (2)	0.024 (2)	0.025 (2)	−0.0013 (17)	−0.0007 (17)	−0.0014 (18)
C4	0.029 (2)	0.028 (2)	0.025 (2)	0.000 (2)	−0.0036 (18)	−0.0085 (19)
C5	0.035 (2)	0.026 (2)	0.039 (3)	−0.005 (2)	0.006 (2)	−0.009 (2)
C6	0.028 (2)	0.0122 (19)	0.036 (3)	−0.0013 (18)	0.004 (2)	−0.0040 (18)
N7	0.0238 (17)	0.0170 (18)	0.0225 (18)	−0.0027 (14)	0.0034 (14)	0.0013 (14)
C7A	0.0168 (19)	0.016 (2)	0.026 (2)	−0.0008 (16)	0.0009 (17)	0.0000 (17)
C8	0.025 (2)	0.016 (2)	0.029 (2)	0.0012 (18)	0.0023 (18)	0.0080 (19)
C9	0.030 (2)	0.025 (2)	0.023 (2)	0.0016 (18)	−0.0020 (18)	0.0095 (19)
C10	0.021 (2)	0.025 (2)	0.0142 (19)	−0.0023 (17)	−0.0013 (16)	0.0010 (17)
C11	0.0160 (19)	0.020 (2)	0.025 (2)	−0.0010 (16)	−0.0053 (16)	0.0061 (18)
O1	0.0365 (16)	0.0186 (15)	0.0210 (15)	−0.0015 (13)	−0.0020 (13)	0.0003 (12)
C11A	0.0168 (19)	0.019 (2)	0.018 (2)	−0.0014 (16)	−0.0025 (16)	−0.0016 (16)
C11B	0.0099 (18)	0.019 (2)	0.026 (2)	−0.0002 (15)	0.0023 (16)	0.0004 (17)
C11C	0.0173 (19)	0.016 (2)	0.023 (2)	0.0017 (17)	0.0041 (16)	−0.0007 (17)
C12	0.034 (2)	0.028 (2)	0.021 (2)	−0.006 (2)	−0.0038 (18)	0.0032 (18)
C13	0.027 (2)	0.023 (2)	0.028 (2)	−0.005 (2)	0.0007 (17)	−0.001 (2)
N1'	0.0235 (18)	0.027 (2)	0.0192 (19)	−0.0045 (15)	−0.0002 (14)	−0.0008 (16)
C2'	0.032 (2)	0.026 (2)	0.011 (2)	−0.0028 (19)	−0.0047 (17)	−0.0008 (17)
N3'	0.031 (2)	0.031 (2)	0.0239 (19)	0.0002 (18)	−0.0032 (16)	−0.0042 (16)
C4'	0.029 (2)	0.042 (3)	0.028 (2)	−0.001 (2)	0.0036 (18)	−0.006 (2)
C5'	0.025 (2)	0.057 (3)	0.016 (2)	−0.013 (2)	0.0024 (18)	−0.001 (2)
C21	0.018 (2)	0.017 (2)	0.026 (2)	−0.0004 (18)	−0.0013 (19)	−0.0012 (15)
C22	0.022 (2)	0.024 (2)	0.027 (2)	0.0020 (19)	−0.0004 (19)	−0.0099 (17)
C23	0.021 (2)	0.033 (2)	0.0156 (19)	0.0011 (18)	0.0017 (17)	−0.0006 (16)
C23A	0.0162 (19)	0.023 (2)	0.022 (2)	−0.0014 (18)	−0.0028 (17)	0.0029 (16)
C24	0.023 (2)	0.033 (2)	0.026 (2)	0.003 (2)	0.0033 (18)	0.0114 (19)
C25	0.022 (3)	0.019 (3)	0.035 (3)	−0.003 (2)	−0.003 (2)	0.009 (2)
C26	0.037 (2)	0.017 (2)	0.033 (2)	−0.001 (2)	0.006 (2)	0.0072 (17)
N27	0.0204 (16)	0.0140 (15)	0.0208 (16)	0.0000 (15)	−0.0016 (15)	−0.0005 (12)
C27A	0.0157 (18)	0.0195 (19)	0.0211 (19)	0.0005 (18)	0.0031 (18)	−0.0012 (15)
C28	0.0232 (19)	0.0115 (18)	0.0278 (19)	−0.0012 (18)	−0.0009 (19)	−0.0021 (16)
C29	0.023 (2)	0.020 (2)	0.021 (2)	0.0004 (16)	0.0012 (17)	−0.0066 (18)
C30	0.0131 (17)	0.0201 (19)	0.0218 (18)	−0.0005 (17)	−0.0014 (18)	0.0021 (15)
C31	0.0118 (17)	0.021 (2)	0.0211 (18)	0.0003 (18)	−0.0015 (17)	−0.0011 (17)
O2	0.0375 (16)	0.0140 (14)	0.0229 (14)	0.0013 (13)	−0.0020 (14)	0.0004 (11)
C31A	0.0178 (18)	0.0117 (18)	0.0211 (19)	0.0026 (17)	0.0011 (18)	−0.0023 (14)
C31B	0.0135 (17)	0.0189 (18)	0.0208 (18)	0.0023 (17)	−0.0029 (17)	0.0019 (15)
C31C	0.0145 (18)	0.0204 (19)	0.0217 (19)	0.0026 (18)	−0.0014 (17)	−0.0014 (15)
C32	0.024 (2)	0.016 (2)	0.021 (2)	−0.0013 (16)	−0.0018 (16)	0.0004 (18)
C33	0.027 (2)	0.021 (2)	0.023 (2)	0.002 (2)	0.0014 (16)	0.0035 (19)
N21'	0.0181 (17)	0.0182 (16)	0.0176 (16)	−0.0023 (15)	0.0013 (15)	0.0014 (12)
C22'	0.027 (2)	0.023 (2)	0.0088 (17)	−0.0026 (19)	−0.0019 (15)	0.0002 (18)
N23'	0.031 (2)	0.0212 (18)	0.0191 (17)	−0.0015 (18)	−0.0020 (18)	0.0018 (14)
C24'	0.023 (2)	0.034 (3)	0.023 (2)	−0.0072 (19)	0.0049 (18)	−0.0015 (18)
C25'	0.018 (2)	0.033 (2)	0.019 (2)	0.0028 (18)	0.0068 (18)	0.0000 (18)
Cl1	0.0266 (5)	0.0304 (5)	0.0221 (5)	0.0052 (5)	0.0005 (5)	−0.0019 (4)
Cl2	0.0222 (5)	0.0237 (5)	0.0305 (5)	0.0016 (4)	−0.0030 (4)	−0.0050 (4)
O1W	0.039 (2)	0.0326 (19)	0.0345 (19)	−0.0074 (16)	−0.0041 (16)	0.0073 (15)
O2W	0.0290 (17)	0.0280 (17)	0.0318 (18)	0.0078 (15)	−0.0094 (15)	−0.0071 (14)

Geometric parameters (Å, º)

C1—C2	1.388 (5)	C23—C23A	1.392 (5)
C1—C11B	1.394 (5)	C23—H23	0.9500
C1—H1	0.9500	C23A—C31C	1.386 (5)
C2—C3	1.406 (5)	C23A—C24	1.513 (5)
C2—H2	0.9500	C24—C25	1.547 (6)
C3—C3A	1.385 (5)	C24—H24A	0.9900
C3—H3	0.9500	C24—H24B	0.9900
C3A—C11C	1.383 (5)	C24—H24C	0.9900
C3A—C4	1.511 (5)	C24—H24D	0.9900
C4—C5	1.531 (6)	C25—C26	1.487 (6)
C4—H4A	0.9900	C25—H25A	0.9900
C4—H4B	0.9900	C25—H25B	0.9900
C5—C6	1.508 (6)	C26—N27	1.458 (4)
C5—H5A	0.9900	C26—H26A	0.9900
C5—H5B	0.9900	C26—H26B	0.9900
C6—N7	1.467 (5)	C26—H26C	0.9900
C6—H6A	0.9900	C26—H26D	0.9900
C6—H6B	0.9900	C25"—H25C	0.9900
N7—C7A	1.359 (5)	C25"—H25D	0.9900
N7—C11C	1.383 (5)	N27—C27A	1.357 (4)
C7A—C11A	1.396 (5)	N27—C31C	1.387 (4)
C7A—C8	1.474 (5)	C27A—C31A	1.390 (5)
C8—C9	1.529 (5)	C27A—C28	1.490 (5)
C8—H8A	0.9900	C28—C29	1.529 (5)
C8—H8B	0.9900	C28—H28A	0.9900
C9—C10	1.540 (5)	C28—H28B	0.9900
C9—H9A	0.9900	C29—C30	1.534 (5)
C9—H9B	0.9900	C29—H29A	0.9900
C10—C11	1.525 (5)	C29—H29B	0.9900
C10—C12	1.534 (5)	C30—C32	1.526 (5)
C10—H10	1.0000	C30—C31	1.540 (5)
C11—O1	1.239 (4)	C30—H30	1.0000
C11—C11A	1.432 (5)	C31—O2	1.228 (4)
C11A—C11B	1.450 (5)	C31—C31A	1.438 (5)
C11B—C11C	1.400 (5)	C31A—C31B	1.442 (5)
C12—N1'	1.468 (5)	C31B—C31C	1.400 (5)
C12—H12A	0.9900	C32—N21'	1.462 (5)
C12—H12B	0.9900	C32—H32A	0.9900
C13—C2'	1.475 (5)	C32—H32B	0.9900
C13—H13A	0.9800	C33—C22'	1.474 (5)
C13—H13B	0.9800	C33—H33A	0.9800
C13—H13C	0.9800	C33—H33B	0.9800
N1'—C2'	1.319 (5)	C33—H33C	0.9800
N1'—C5'	1.389 (5)	N21'—C22'	1.334 (5)
C2'—N3'	1.331 (5)	N21'—C25'	1.389 (5)
N3'—C4'	1.375 (5)	C22'—N23'	1.334 (5)
N3'—H3'	0.88 (4)	N23'—C24'	1.376 (5)
C4'—C5'	1.364 (7)	N23'—H23'	0.88 (4)
C4'—H4'	0.9500	C24'—C25'	1.335 (6)
C5'—H5'	0.9500	C24'—H24'	0.9500
C21—C22	1.383 (5)	C25'—H25'	0.9500
C21—C31B	1.413 (5)	O1W—H01	0.84 (3)
C21—H21	0.9500	O1W—H02	0.84 (3)
C22—C23	1.405 (5)	O2W—H03	0.85 (3)
C22—H22	0.9500	O2W—H04	0.84 (3)
C2—C1—C11B	118.6 (4)	C31C—C23A—C24	117.2 (3)
C2—C1—H1	120.7	C23—C23A—C24	127.6 (3)
C11B—C1—H1	120.7	C25"—C24—C23A	115.1 (7)
C1—C2—C3	121.4 (4)	C23A—C24—C25	111.3 (3)
C1—C2—H2	119.3	C23A—C24—H24A	109.4
C3—C2—H2	119.3	C25—C24—H24A	109.4
C3A—C3—C2	121.3 (4)	C23A—C24—H24B	109.4
C3A—C3—H3	119.3	C25—C24—H24B	109.4
C2—C3—H3	119.3	H24A—C24—H24B	108.0
C11C—C3A—C3	115.6 (4)	C25"—C24—H24C	108.5
C11C—C3A—C4	116.9 (3)	C23A—C24—H24C	108.5
C3—C3A—C4	127.4 (3)	C25"—C24—H24D	108.5
C3A—C4—C5	111.1 (3)	C23A—C24—H24D	108.5
C3A—C4—H4A	109.4	H24C—C24—H24D	107.5
C5—C4—H4A	109.4	C26—C25—C24	115.7 (4)
C3A—C4—H4B	109.4	C26—C25—H25A	108.3
C5—C4—H4B	109.4	C24—C25—H25A	108.3
H4A—C4—H4B	108.0	C26—C25—H25B	108.3
C6—C5—C4	114.9 (3)	C24—C25—H25B	108.3
C6—C5—H5A	108.5	H25A—C25—H25B	107.4
C4—C5—H5A	108.5	N27—C26—C25	110.4 (4)
C6—C5—H5B	108.5	N27—C26—C25"	111.8 (6)
C4—C5—H5B	108.5	N27—C26—H26A	109.6
H5A—C5—H5B	107.5	C25—C26—H26A	109.6
N7—C6—C5	109.9 (3)	N27—C26—H26B	109.6
N7—C6—H6A	109.7	C25—C26—H26B	109.6
C5—C6—H6A	109.7	H26A—C26—H26B	108.1
N7—C6—H6B	109.7	N27—C26—H26C	109.3
C5—C6—H6B	109.7	C25"—C26—H26C	109.3
H6A—C6—H6B	108.2	N27—C26—H26D	109.3
C7A—N7—C11C	109.6 (3)	C25"—C26—H26D	109.3
C7A—N7—C6	129.4 (3)	H26C—C26—H26D	107.9
C11C—N7—C6	121.0 (3)	C24—C25"—C26	120.0 (10)
N7—C7A—C11A	108.6 (3)	C24—C25"—H25C	107.3
N7—C7A—C8	126.1 (3)	C26—C25"—H25C	107.3
C11A—C7A—C8	125.3 (4)	C24—C25"—H25D	107.3
C7A—C8—C9	109.7 (3)	C26—C25"—H25D	107.3
C7A—C8—H8A	109.7	H25C—C25"—H25D	106.9
C9—C8—H8A	109.7	C27A—N27—C31C	108.9 (3)
C7A—C8—H8B	109.7	C27A—N27—C26	129.5 (3)
C9—C8—H8B	109.7	C31C—N27—C26	121.5 (3)
H8A—C8—H8B	108.2	N27—C27A—C31A	109.6 (3)
C8—C9—C10	113.1 (3)	N27—C27A—C28	125.7 (3)
C8—C9—H9A	109.0	C31A—C27A—C28	124.7 (3)
C10—C9—H9A	109.0	C27A—C28—C29	109.0 (3)
C8—C9—H9B	109.0	C27A—C28—H28A	109.9
C10—C9—H9B	109.0	C29—C28—H28A	109.9
H9A—C9—H9B	107.8	C27A—C28—H28B	109.9
C11—C10—C12	114.0 (3)	C29—C28—H28B	109.9
C11—C10—C9	111.3 (3)	H28A—C28—H28B	108.3
C12—C10—C9	107.9 (3)	C28—C29—C30	113.8 (3)
C11—C10—H10	107.8	C28—C29—H29A	108.8
C12—C10—H10	107.8	C30—C29—H29A	108.8
C9—C10—H10	107.8	C28—C29—H29B	108.8
O1—C11—C11A	122.3 (3)	C30—C29—H29B	108.8
O1—C11—C10	121.8 (3)	H29A—C29—H29B	107.7
C11A—C11—C10	115.8 (3)	C32—C30—C29	107.2 (3)
C7A—C11A—C11	121.8 (4)	C32—C30—C31	113.8 (3)
C7A—C11A—C11B	107.4 (3)	C29—C30—C31	112.3 (3)
C11—C11A—C11B	130.6 (3)	C32—C30—H30	107.8
C1—C11B—C11C	118.0 (3)	C29—C30—H30	107.8
C1—C11B—C11A	136.5 (3)	C31—C30—H30	107.8
C11C—C11B—C11A	105.4 (3)	O2—C31—C31A	122.8 (3)
N7—C11C—C3A	125.9 (3)	O2—C31—C30	121.7 (3)
N7—C11C—C11B	109.0 (3)	C31A—C31—C30	115.4 (3)
C3A—C11C—C11B	125.0 (4)	C27A—C31A—C31	122.9 (3)
N1'—C12—C10	115.5 (3)	C27A—C31A—C31B	106.8 (3)
N1'—C12—H12A	108.4	C31—C31A—C31B	130.3 (3)
C10—C12—H12A	108.4	C31C—C31B—C21	116.9 (3)
N1'—C12—H12B	108.4	C31C—C31B—C31A	106.1 (3)
C10—C12—H12B	108.4	C21—C31B—C31A	136.9 (3)
H12A—C12—H12B	107.5	C23A—C31C—N27	125.4 (3)
C2'—C13—H13A	109.5	C23A—C31C—C31B	126.0 (3)
C2'—C13—H13B	109.5	N27—C31C—C31B	108.6 (3)
H13A—C13—H13B	109.5	N21'—C32—C30	115.1 (3)
C2'—C13—H13C	109.5	N21'—C32—H32A	108.5
H13A—C13—H13C	109.5	C30—C32—H32A	108.5
H13B—C13—H13C	109.5	N21'—C32—H32B	108.5
C2'—N1'—C5'	109.9 (4)	C30—C32—H32B	108.5
C2'—N1'—C12	126.2 (3)	H32A—C32—H32B	107.5
C5'—N1'—C12	123.9 (4)	C22'—C33—H33A	109.5
N1'—C2'—N3'	107.8 (4)	C22'—C33—H33B	109.5
N1'—C2'—C13	127.1 (4)	H33A—C33—H33B	109.5
N3'—C2'—C13	125.1 (4)	C22'—C33—H33C	109.5
C2'—N3'—C4'	109.7 (4)	H33A—C33—H33C	109.5
C2'—N3'—H3'	122 (4)	H33B—C33—H33C	109.5
C4'—N3'—H3'	128 (4)	C22'—N21'—C25'	108.7 (3)
C5'—C4'—N3'	106.7 (4)	C22'—N21'—C32	126.3 (3)
C5'—C4'—H4'	126.6	C25'—N21'—C32	124.9 (3)
N3'—C4'—H4'	126.6	N21'—C22'—N23'	107.7 (3)
C4'—C5'—N1'	105.9 (4)	N21'—C22'—C33	126.7 (4)
C4'—C5'—H5'	127.0	N23'—C22'—C33	125.6 (4)
N1'—C5'—H5'	127.0	C22'—N23'—C24'	109.1 (3)
C22—C21—C31B	118.7 (3)	C22'—N23'—H23'	125 (3)
C22—C21—H21	120.6	C24'—N23'—H23'	125 (3)
C31B—C21—H21	120.6	C25'—C24'—N23'	107.4 (4)
C21—C22—C23	121.8 (3)	C25'—C24'—H24'	126.3
C21—C22—H22	119.1	N23'—C24'—H24'	126.3
C23—C22—H22	119.1	C24'—C25'—N21'	107.1 (4)
C23A—C23—C22	121.3 (3)	C24'—C25'—H25'	126.5
C23A—C23—H23	119.3	N21'—C25'—H25'	126.5
C22—C23—H23	119.3	H01—O1W—H02	106 (5)
C31C—C23A—C23	115.2 (3)	H03—O2W—H04	106 (5)
C11B—C1—C2—C3	1.5 (6)	C22—C23—C23A—C24	179.7 (4)
C1—C2—C3—C3A	−1.5 (6)	C31C—C23A—C24—C25"	18.0 (9)
C2—C3—C3A—C11C	1.4 (6)	C23—C23A—C24—C25"	−160.8 (8)
C2—C3—C3A—C4	−176.8 (4)	C31C—C23A—C24—C25	−21.6 (5)
C11C—C3A—C4—C5	24.5 (5)	C23—C23A—C24—C25	159.5 (4)
C3—C3A—C4—C5	−157.4 (4)	C23A—C24—C25—C26	47.0 (6)
C3A—C4—C5—C6	−50.0 (5)	C24—C25—C26—N27	−47.5 (6)
C4—C5—C6—N7	48.8 (5)	C23A—C24—C25"—C26	−34.9 (16)
C5—C6—N7—C7A	160.7 (4)	N27—C26—C25"—C24	32.9 (15)
C5—C6—N7—C11C	−23.5 (5)	C25—C26—N27—C27A	−160.0 (4)
C11C—N7—C7A—C11A	1.4 (4)	C25"—C26—N27—C27A	161.2 (8)
C6—N7—C7A—C11A	177.5 (4)	C25—C26—N27—C31C	24.4 (6)
C11C—N7—C7A—C8	−178.6 (4)	C25"—C26—N27—C31C	−14.4 (9)
C6—N7—C7A—C8	−2.5 (6)	C31C—N27—C27A—C31A	−0.7 (5)
N7—C7A—C8—C9	−164.4 (4)	C26—N27—C27A—C31A	−176.7 (4)
C11A—C7A—C8—C9	15.6 (5)	C31C—N27—C27A—C28	178.6 (4)
C7A—C8—C9—C10	−45.0 (4)	C26—N27—C27A—C28	2.6 (7)
C8—C9—C10—C11	56.1 (4)	N27—C27A—C28—C29	−157.9 (4)
C8—C9—C10—C12	−178.1 (3)	C31A—C27A—C28—C29	21.4 (5)
C12—C10—C11—O1	24.5 (5)	C27A—C28—C29—C30	−47.4 (4)
C9—C10—C11—O1	146.9 (3)	C28—C29—C30—C32	179.5 (3)
C12—C10—C11—C11A	−157.6 (3)	C28—C29—C30—C31	53.9 (4)
C9—C10—C11—C11A	−35.2 (4)	C32—C30—C31—O2	28.7 (5)
N7—C7A—C11A—C11	−175.7 (3)	C29—C30—C31—O2	150.6 (3)
C8—C7A—C11A—C11	4.3 (6)	C32—C30—C31—C31A	−152.7 (3)
N7—C7A—C11A—C11B	−0.8 (4)	C29—C30—C31—C31A	−30.8 (4)
C8—C7A—C11A—C11B	179.2 (3)	N27—C27A—C31A—C31	179.2 (3)
O1—C11—C11A—C7A	−176.0 (4)	C28—C27A—C31A—C31	−0.2 (6)
C10—C11—C11A—C7A	6.1 (5)	N27—C27A—C31A—C31B	0.1 (5)
O1—C11—C11A—C11B	10.4 (6)	C28—C27A—C31A—C31B	−179.2 (4)
C10—C11—C11A—C11B	−167.5 (4)	O2—C31—C31A—C27A	−176.6 (4)
C2—C1—C11B—C11C	−1.4 (5)	C30—C31—C31A—C27A	4.8 (5)
C2—C1—C11B—C11A	175.7 (4)	O2—C31—C31A—C31B	2.1 (6)
C7A—C11A—C11B—C1	−177.5 (4)	C30—C31—C31A—C31B	−176.4 (4)
C11—C11A—C11B—C1	−3.2 (7)	C22—C21—C31B—C31C	1.4 (5)
C7A—C11A—C11B—C11C	−0.1 (4)	C22—C21—C31B—C31A	−177.2 (4)
C11—C11A—C11B—C11C	174.2 (4)	C27A—C31A—C31B—C31C	0.5 (4)
C7A—N7—C11C—C3A	175.9 (4)	C31—C31A—C31B—C31C	−178.4 (4)
C6—N7—C11C—C3A	−0.6 (6)	C27A—C31A—C31B—C21	179.2 (4)
C7A—N7—C11C—C11B	−1.5 (4)	C31—C31A—C31B—C21	0.2 (8)
C6—N7—C11C—C11B	−178.0 (3)	C23—C23A—C31C—N27	178.4 (4)
C3—C3A—C11C—N7	−178.4 (4)	C24—C23A—C31C—N27	−0.5 (6)
C4—C3A—C11C—N7	0.0 (6)	C23—C23A—C31C—C31B	0.8 (6)
C3—C3A—C11C—C11B	−1.4 (6)	C24—C23A—C31C—C31B	−178.2 (4)
C4—C3A—C11C—C11B	176.9 (4)	C27A—N27—C31C—C23A	−177.0 (4)
C1—C11B—C11C—N7	178.9 (3)	C26—N27—C31C—C23A	−0.5 (6)
C11A—C11B—C11C—N7	0.9 (4)	C27A—N27—C31C—C31B	1.0 (4)
C1—C11B—C11C—C3A	1.5 (6)	C26—N27—C31C—C31B	177.4 (4)
C11A—C11B—C11C—C3A	−176.5 (4)	C21—C31B—C31C—C23A	−1.9 (6)
C11—C10—C12—N1'	−59.5 (4)	C31A—C31B—C31C—C23A	177.0 (4)
C9—C10—C12—N1'	176.3 (3)	C21—C31B—C31C—N27	−179.9 (3)
C10—C12—N1'—C2'	108.6 (4)	C31A—C31B—C31C—N27	−0.9 (4)
C10—C12—N1'—C5'	−72.7 (5)	C29—C30—C32—N21'	177.5 (3)
C5'—N1'—C2'—N3'	1.0 (4)	C31—C30—C32—N21'	−57.8 (4)
C12—N1'—C2'—N3'	179.8 (3)	C30—C32—N21'—C22'	113.7 (4)
C5'—N1'—C2'—C13	−177.4 (4)	C30—C32—N21'—C25'	−64.6 (5)
C12—N1'—C2'—C13	1.4 (6)	C25'—N21'—C22'—N23'	−0.5 (4)
N1'—C2'—N3'—C4'	−0.7 (4)	C32—N21'—C22'—N23'	−179.1 (3)
C13—C2'—N3'—C4'	177.7 (3)	C25'—N21'—C22'—C33	−178.9 (3)
C2'—N3'—C4'—C5'	0.1 (5)	C32—N21'—C22'—C33	2.6 (6)
N3'—C4'—C5'—N1'	0.5 (5)	N21'—C22'—N23'—C24'	0.5 (4)
C2'—N1'—C5'—C4'	−0.9 (5)	C33—C22'—N23'—C24'	178.8 (3)
C12—N1'—C5'—C4'	−179.7 (3)	C22'—N23'—C24'—C25'	−0.2 (5)
C31B—C21—C22—C23	0.1 (6)	N23'—C24'—C25'—N21'	−0.1 (5)
C21—C22—C23—C23A	−1.2 (6)	C22'—N21'—C25'—C24'	0.4 (4)
C22—C23—C23A—C31C	0.8 (6)	C32—N21'—C25'—C24'	179.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3′—H3′···O1W^i	0.88 (4)	1.85 (4)	2.724 (5)	170 (5)
N23′—H23′···O2W^i	0.88 (4)	1.87 (4)	2.741 (5)	167 (4)
O1W—H01···Cl2	0.84 (3)	2.28 (3)	3.117 (3)	173 (5)
O1W—H02···Cl1^ii	0.84 (3)	2.27 (3)	3.113 (4)	178 (5)
O2W—H03···Cl1	0.85 (3)	2.24 (3)	3.076 (3)	170 (4)
O2W—H04···Cl2	0.84 (3)	2.26 (3)	3.086 (3)	165 (5)
C9—H9A···Cl1	0.99	2.88	3.797 (4)	154
C12—H12B···Cl1	0.99	2.85	3.775 (4)	156
C13—H13B···Cl1^iii	0.98	2.91	3.685 (4)	137
C29—H29A···Cl1	0.99	2.81	3.761 (4)	161
C32—H32B···Cl1	0.99	2.96	3.887 (4)	156
C24′—H24′···Cl1^iii	0.95	2.70	3.632 (4)	167
C12—H12A···Cl2^iv	0.99	2.88	3.528 (4)	124
C13—H13C···Cl2^iv	0.98	2.85	3.782 (4)	159
C5′—H5′···Cl2	0.95	2.73	3.507 (4)	139
C33—H33C···Cl2	0.98	2.73	3.665 (4)	160
C25′—H25′···Cl2^iv	0.95	2.55	3.438 (4)	155
C5—H5A···O1^v	0.99	2.62	3.479 (5)	145
C2—H2···O2^vi	0.95	2.61	3.482 (5)	152
C25—H25B···O2^vii	0.99	2.54	3.398 (6)	145
C3—H3···O2W^v	0.95	2.53	3.479 (5)	173
C23—H23···O1W^vii	0.95	2.67	3.586 (5)	164

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