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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802022481/bt6215sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802022481/bt6215Isup2.hkl
Contains datablock I

CCDC reference: 202994

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


Yellow Alert 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 top

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 top
Crystal data top
C20H22N3O+·Cl·H2ODx = 1.348 Mg m3
Mr = 373.87Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 5470 reflections
a = 7.396 (2) Åθ = 2–25°
b = 16.460 (3) ŵ = 0.23 mm1
c = 30.263 (6) ÅT = 123 K
V = 3684.2 (14) Å3Lath, colourless
Z = 80.70 × 0.23 × 0.04 mm
F(000) = 1584
Data collection top
Stoe-Huber-Siemens area-detector
diffractometer
5335 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.112
Graphite monochromatorθmax = 25.1°, θmin = 2.4°
Detector resolution: 8.192 pixels mm-1h = 88
φ–scank = 019
61630 measured reflectionsl = 036
6553 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.105 w = 1/[σ2(Fo2) + (0.018P)2 + 3.9789P]
where P = (Fo2 + 2Fc2)/3
S = 1.15(Δ/σ)max < 0.001
6553 reflectionsΔρmax = 0.36 e Å3
500 parametersΔρmin = 0.27 e Å3
15 restraintsAbsolute structure: Flack (1983), 2820 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (9)
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.5799 (5)0.1127 (2)0.51381 (13)0.0208 (9)
H10.57640.06230.49860.025*
C20.5867 (5)0.1151 (2)0.55962 (13)0.0220 (9)
H20.59080.06560.57570.026*
C30.5877 (5)0.1892 (2)0.58271 (13)0.0245 (9)
H30.58940.18880.61410.029*
C3A0.5862 (5)0.2629 (2)0.56062 (13)0.0214 (9)
C40.5962 (5)0.3469 (2)0.58063 (13)0.0271 (9)
H4A0.72390.36040.58710.033*
H4B0.52830.34770.60880.033*
C50.5173 (6)0.4106 (3)0.54923 (14)0.0333 (11)
H5A0.38430.40380.54830.040*
H5B0.54270.46520.56140.040*
C60.5887 (5)0.4070 (2)0.50259 (14)0.0255 (9)
H6A0.51540.44270.48330.031*
H6B0.71520.42670.50190.031*
N70.5811 (4)0.32330 (18)0.48615 (10)0.0211 (7)
C7A0.5853 (5)0.2956 (2)0.44388 (13)0.0196 (8)
C80.5921 (5)0.3460 (2)0.40364 (12)0.0234 (8)
H8A0.71520.36860.39990.028*
H8B0.50620.39180.40640.028*
C90.5428 (5)0.2944 (2)0.36339 (13)0.0258 (9)
H9A0.57610.32440.33620.031*
H9B0.41030.28600.36290.031*
C100.6374 (5)0.2111 (2)0.36299 (12)0.0200 (8)
H100.77080.22080.36170.024*
C110.5978 (5)0.1635 (2)0.40515 (12)0.0204 (8)
O10.5855 (4)0.08844 (15)0.40521 (9)0.0254 (6)
C11A0.5822 (5)0.2108 (2)0.44469 (12)0.0177 (8)
C11B0.5783 (5)0.1859 (2)0.49066 (12)0.0184 (8)
C11C0.5796 (5)0.2582 (2)0.51502 (12)0.0188 (8)
C120.5820 (6)0.1668 (2)0.32048 (12)0.0275 (9)
H12A0.44950.15860.32100.033*
H12B0.60990.20250.29500.033*
C130.3995 (5)0.0009 (3)0.32620 (12)0.0260 (8)
H13A0.37540.01220.35720.031*
H13B0.37390.05850.32090.031*
H13C0.32200.03240.30720.031*
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)
H4'0.98720.02920.28970.039*
C5'0.8491 (6)0.0786 (3)0.30102 (14)0.0325 (12)
H5'0.93510.12050.29630.039*
C210.7671 (5)0.1054 (2)0.01679 (12)0.0206 (8)
H210.76440.05440.00210.025*
C220.7743 (5)0.1094 (2)0.06242 (12)0.0243 (9)
H220.77640.06030.07900.029*
C230.7786 (5)0.1839 (2)0.08498 (12)0.0233 (9)
H230.78600.18420.11630.028*
C23A0.7723 (5)0.2575 (2)0.06235 (11)0.0204 (8)
C240.7767 (5)0.3422 (2)0.08171 (12)0.0273 (9)
H24A0.70490.34320.10930.033*0.767 (12)
H24B0.90290.35670.08920.033*0.767 (12)
H24C0.86330.34270.10670.033*0.233 (12)
H24D0.65560.35480.09380.033*0.233 (12)
C250.6996 (8)0.4054 (3)0.04893 (17)0.0251 (17)0.767 (12)
H25A0.72740.46040.06030.030*0.767 (12)
H25B0.56640.39970.04830.030*0.767 (12)
C260.7678 (6)0.3997 (2)0.00283 (13)0.0291 (9)
H26A0.89400.41970.00160.035*0.767 (12)
H26B0.69320.43440.01670.035*0.767 (12)
H26C0.85420.43070.01570.035*0.233 (12)
H26D0.64700.42480.00060.035*0.233 (12)
C25"0.826 (2)0.4052 (9)0.0514 (4)0.014 (5)*0.233 (12)
H25C0.77820.45690.06330.017*0.233 (12)
H25D0.95960.40950.05180.017*0.233 (12)
N270.7609 (4)0.31583 (16)0.01259 (9)0.0184 (6)
C27A0.7618 (5)0.2865 (2)0.05449 (11)0.0188 (8)
C280.7631 (5)0.3363 (2)0.09559 (11)0.0208 (8)
H28A0.63880.35460.10260.025*
H28B0.83970.38500.09130.025*
C290.8375 (5)0.2850 (2)0.13354 (13)0.0211 (9)
H29A0.81590.31400.16170.025*
H29B0.96980.27930.12980.025*
C300.7533 (5)0.2000 (2)0.13663 (11)0.0183 (7)
H300.62210.20680.14380.022*
C310.7670 (5)0.1530 (2)0.09276 (11)0.0180 (7)
O20.7765 (4)0.07851 (14)0.09180 (8)0.0248 (6)
C31A0.7633 (5)0.2021 (2)0.05346 (11)0.0168 (8)
C31B0.7638 (5)0.1786 (2)0.00754 (11)0.0177 (7)
C31C0.7640 (5)0.2510 (2)0.01673 (11)0.0189 (8)
C320.8427 (5)0.1569 (2)0.17555 (12)0.0202 (8)
H32A0.97410.15290.16970.024*
H32B0.82690.19080.20230.024*
C331.0553 (5)0.0035 (3)0.16752 (12)0.0237 (9)
H33A1.06860.01050.13620.028*
H33B1.09300.05990.17220.028*
H33C1.13090.03270.18540.028*
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)
H24'0.48350.05230.21200.032*
C25'0.5987 (5)0.0581 (2)0.19870 (13)0.0233 (9)
H25'0.50510.09630.20410.028*
Cl10.75471 (13)0.34232 (6)0.25214 (3)0.0264 (2)
Cl21.22607 (12)0.15229 (6)0.24328 (3)0.0255 (2)
O1W1.4041 (5)0.30365 (19)0.19926 (11)0.0353 (7)
H011.354 (6)0.265 (2)0.2129 (15)0.057 (18)*
H021.501 (5)0.313 (3)0.2129 (15)0.065 (19)*
O2W1.0985 (4)0.29336 (18)0.30276 (10)0.0296 (7)
H030.998 (4)0.301 (3)0.2899 (14)0.044 (15)*
H041.154 (6)0.258 (3)0.2875 (16)0.07 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.019 (2)0.015 (2)0.029 (2)0.0009 (16)0.0006 (18)0.0008 (17)
C20.020 (2)0.024 (2)0.022 (2)0.0008 (17)0.0027 (18)0.0086 (18)
C30.022 (2)0.030 (2)0.022 (2)0.0021 (18)0.0019 (17)0.0021 (18)
C3A0.016 (2)0.024 (2)0.025 (2)0.0013 (17)0.0007 (17)0.0014 (18)
C40.029 (2)0.028 (2)0.025 (2)0.000 (2)0.0036 (18)0.0085 (19)
C50.035 (2)0.026 (2)0.039 (3)0.005 (2)0.006 (2)0.009 (2)
C60.028 (2)0.0122 (19)0.036 (3)0.0013 (18)0.004 (2)0.0040 (18)
N70.0238 (17)0.0170 (18)0.0225 (18)0.0027 (14)0.0034 (14)0.0013 (14)
C7A0.0168 (19)0.016 (2)0.026 (2)0.0008 (16)0.0009 (17)0.0000 (17)
C80.025 (2)0.016 (2)0.029 (2)0.0012 (18)0.0023 (18)0.0080 (19)
C90.030 (2)0.025 (2)0.023 (2)0.0016 (18)0.0020 (18)0.0095 (19)
C100.021 (2)0.025 (2)0.0142 (19)0.0023 (17)0.0013 (16)0.0010 (17)
C110.0160 (19)0.020 (2)0.025 (2)0.0010 (16)0.0053 (16)0.0061 (18)
O10.0365 (16)0.0186 (15)0.0210 (15)0.0015 (13)0.0020 (13)0.0003 (12)
C11A0.0168 (19)0.019 (2)0.018 (2)0.0014 (16)0.0025 (16)0.0016 (16)
C11B0.0099 (18)0.019 (2)0.026 (2)0.0002 (15)0.0023 (16)0.0004 (17)
C11C0.0173 (19)0.016 (2)0.023 (2)0.0017 (17)0.0041 (16)0.0007 (17)
C120.034 (2)0.028 (2)0.021 (2)0.006 (2)0.0038 (18)0.0032 (18)
C130.027 (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)
C210.018 (2)0.017 (2)0.026 (2)0.0004 (18)0.0013 (19)0.0012 (15)
C220.022 (2)0.024 (2)0.027 (2)0.0020 (19)0.0004 (19)0.0099 (17)
C230.021 (2)0.033 (2)0.0156 (19)0.0011 (18)0.0017 (17)0.0006 (16)
C23A0.0162 (19)0.023 (2)0.022 (2)0.0014 (18)0.0028 (17)0.0029 (16)
C240.023 (2)0.033 (2)0.026 (2)0.003 (2)0.0033 (18)0.0114 (19)
C250.022 (3)0.019 (3)0.035 (3)0.003 (2)0.003 (2)0.009 (2)
C260.037 (2)0.017 (2)0.033 (2)0.001 (2)0.006 (2)0.0072 (17)
N270.0204 (16)0.0140 (15)0.0208 (16)0.0000 (15)0.0016 (15)0.0005 (12)
C27A0.0157 (18)0.0195 (19)0.0211 (19)0.0005 (18)0.0031 (18)0.0012 (15)
C280.0232 (19)0.0115 (18)0.0278 (19)0.0012 (18)0.0009 (19)0.0021 (16)
C290.023 (2)0.020 (2)0.021 (2)0.0004 (16)0.0012 (17)0.0066 (18)
C300.0131 (17)0.0201 (19)0.0218 (18)0.0005 (17)0.0014 (18)0.0021 (15)
C310.0118 (17)0.021 (2)0.0211 (18)0.0003 (18)0.0015 (17)0.0011 (17)
O20.0375 (16)0.0140 (14)0.0229 (14)0.0013 (13)0.0020 (14)0.0004 (11)
C31A0.0178 (18)0.0117 (18)0.0211 (19)0.0026 (17)0.0011 (18)0.0023 (14)
C31B0.0135 (17)0.0189 (18)0.0208 (18)0.0023 (17)0.0029 (17)0.0019 (15)
C31C0.0145 (18)0.0204 (19)0.0217 (19)0.0026 (18)0.0014 (17)0.0014 (15)
C320.024 (2)0.016 (2)0.021 (2)0.0013 (16)0.0018 (16)0.0004 (18)
C330.027 (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)
Cl10.0266 (5)0.0304 (5)0.0221 (5)0.0052 (5)0.0005 (5)0.0019 (4)
Cl20.0222 (5)0.0237 (5)0.0305 (5)0.0016 (4)0.0030 (4)0.0050 (4)
O1W0.039 (2)0.0326 (19)0.0345 (19)0.0074 (16)0.0041 (16)0.0073 (15)
O2W0.0290 (17)0.0280 (17)0.0318 (18)0.0078 (15)0.0094 (15)0.0071 (14)
Geometric parameters (Å, º) top
C1—C21.388 (5)C23—C23A1.392 (5)
C1—C11B1.394 (5)C23—H230.9500
C1—H10.9500C23A—C31C1.386 (5)
C2—C31.406 (5)C23A—C241.513 (5)
C2—H20.9500C24—C251.547 (6)
C3—C3A1.385 (5)C24—H24A0.9900
C3—H30.9500C24—H24B0.9900
C3A—C11C1.383 (5)C24—H24C0.9900
C3A—C41.511 (5)C24—H24D0.9900
C4—C51.531 (6)C25—C261.487 (6)
C4—H4A0.9900C25—H25A0.9900
C4—H4B0.9900C25—H25B0.9900
C5—C61.508 (6)C26—N271.458 (4)
C5—H5A0.9900C26—H26A0.9900
C5—H5B0.9900C26—H26B0.9900
C6—N71.467 (5)C26—H26C0.9900
C6—H6A0.9900C26—H26D0.9900
C6—H6B0.9900C25"—H25C0.9900
N7—C7A1.359 (5)C25"—H25D0.9900
N7—C11C1.383 (5)N27—C27A1.357 (4)
C7A—C11A1.396 (5)N27—C31C1.387 (4)
C7A—C81.474 (5)C27A—C31A1.390 (5)
C8—C91.529 (5)C27A—C281.490 (5)
C8—H8A0.9900C28—C291.529 (5)
C8—H8B0.9900C28—H28A0.9900
C9—C101.540 (5)C28—H28B0.9900
C9—H9A0.9900C29—C301.534 (5)
C9—H9B0.9900C29—H29A0.9900
C10—C111.525 (5)C29—H29B0.9900
C10—C121.534 (5)C30—C321.526 (5)
C10—H101.0000C30—C311.540 (5)
C11—O11.239 (4)C30—H301.0000
C11—C11A1.432 (5)C31—O21.228 (4)
C11A—C11B1.450 (5)C31—C31A1.438 (5)
C11B—C11C1.400 (5)C31A—C31B1.442 (5)
C12—N1'1.468 (5)C31B—C31C1.400 (5)
C12—H12A0.9900C32—N21'1.462 (5)
C12—H12B0.9900C32—H32A0.9900
C13—C2'1.475 (5)C32—H32B0.9900
C13—H13A0.9800C33—C22'1.474 (5)
C13—H13B0.9800C33—H33A0.9800
C13—H13C0.9800C33—H33B0.9800
N1'—C2'1.319 (5)C33—H33C0.9800
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'—H4'0.9500C24'—C25'1.335 (6)
C5'—H5'0.9500C24'—H24'0.9500
C21—C221.383 (5)C25'—H25'0.9500
C21—C31B1.413 (5)O1W—H010.84 (3)
C21—H210.9500O1W—H020.84 (3)
C22—C231.405 (5)O2W—H030.85 (3)
C22—H220.9500O2W—H040.84 (3)
C2—C1—C11B118.6 (4)C31C—C23A—C24117.2 (3)
C2—C1—H1120.7C23—C23A—C24127.6 (3)
C11B—C1—H1120.7C25"—C24—C23A115.1 (7)
C1—C2—C3121.4 (4)C23A—C24—C25111.3 (3)
C1—C2—H2119.3C23A—C24—H24A109.4
C3—C2—H2119.3C25—C24—H24A109.4
C3A—C3—C2121.3 (4)C23A—C24—H24B109.4
C3A—C3—H3119.3C25—C24—H24B109.4
C2—C3—H3119.3H24A—C24—H24B108.0
C11C—C3A—C3115.6 (4)C25"—C24—H24C108.5
C11C—C3A—C4116.9 (3)C23A—C24—H24C108.5
C3—C3A—C4127.4 (3)C25"—C24—H24D108.5
C3A—C4—C5111.1 (3)C23A—C24—H24D108.5
C3A—C4—H4A109.4H24C—C24—H24D107.5
C5—C4—H4A109.4C26—C25—C24115.7 (4)
C3A—C4—H4B109.4C26—C25—H25A108.3
C5—C4—H4B109.4C24—C25—H25A108.3
H4A—C4—H4B108.0C26—C25—H25B108.3
C6—C5—C4114.9 (3)C24—C25—H25B108.3
C6—C5—H5A108.5H25A—C25—H25B107.4
C4—C5—H5A108.5N27—C26—C25110.4 (4)
C6—C5—H5B108.5N27—C26—C25"111.8 (6)
C4—C5—H5B108.5N27—C26—H26A109.6
H5A—C5—H5B107.5C25—C26—H26A109.6
N7—C6—C5109.9 (3)N27—C26—H26B109.6
N7—C6—H6A109.7C25—C26—H26B109.6
C5—C6—H6A109.7H26A—C26—H26B108.1
N7—C6—H6B109.7N27—C26—H26C109.3
C5—C6—H6B109.7C25"—C26—H26C109.3
H6A—C6—H6B108.2N27—C26—H26D109.3
C7A—N7—C11C109.6 (3)C25"—C26—H26D109.3
C7A—N7—C6129.4 (3)H26C—C26—H26D107.9
C11C—N7—C6121.0 (3)C24—C25"—C26120.0 (10)
N7—C7A—C11A108.6 (3)C24—C25"—H25C107.3
N7—C7A—C8126.1 (3)C26—C25"—H25C107.3
C11A—C7A—C8125.3 (4)C24—C25"—H25D107.3
C7A—C8—C9109.7 (3)C26—C25"—H25D107.3
C7A—C8—H8A109.7H25C—C25"—H25D106.9
C9—C8—H8A109.7C27A—N27—C31C108.9 (3)
C7A—C8—H8B109.7C27A—N27—C26129.5 (3)
C9—C8—H8B109.7C31C—N27—C26121.5 (3)
H8A—C8—H8B108.2N27—C27A—C31A109.6 (3)
C8—C9—C10113.1 (3)N27—C27A—C28125.7 (3)
C8—C9—H9A109.0C31A—C27A—C28124.7 (3)
C10—C9—H9A109.0C27A—C28—C29109.0 (3)
C8—C9—H9B109.0C27A—C28—H28A109.9
C10—C9—H9B109.0C29—C28—H28A109.9
H9A—C9—H9B107.8C27A—C28—H28B109.9
C11—C10—C12114.0 (3)C29—C28—H28B109.9
C11—C10—C9111.3 (3)H28A—C28—H28B108.3
C12—C10—C9107.9 (3)C28—C29—C30113.8 (3)
C11—C10—H10107.8C28—C29—H29A108.8
C12—C10—H10107.8C30—C29—H29A108.8
C9—C10—H10107.8C28—C29—H29B108.8
O1—C11—C11A122.3 (3)C30—C29—H29B108.8
O1—C11—C10121.8 (3)H29A—C29—H29B107.7
C11A—C11—C10115.8 (3)C32—C30—C29107.2 (3)
C7A—C11A—C11121.8 (4)C32—C30—C31113.8 (3)
C7A—C11A—C11B107.4 (3)C29—C30—C31112.3 (3)
C11—C11A—C11B130.6 (3)C32—C30—H30107.8
C1—C11B—C11C118.0 (3)C29—C30—H30107.8
C1—C11B—C11A136.5 (3)C31—C30—H30107.8
C11C—C11B—C11A105.4 (3)O2—C31—C31A122.8 (3)
N7—C11C—C3A125.9 (3)O2—C31—C30121.7 (3)
N7—C11C—C11B109.0 (3)C31A—C31—C30115.4 (3)
C3A—C11C—C11B125.0 (4)C27A—C31A—C31122.9 (3)
N1'—C12—C10115.5 (3)C27A—C31A—C31B106.8 (3)
N1'—C12—H12A108.4C31—C31A—C31B130.3 (3)
C10—C12—H12A108.4C31C—C31B—C21116.9 (3)
N1'—C12—H12B108.4C31C—C31B—C31A106.1 (3)
C10—C12—H12B108.4C21—C31B—C31A136.9 (3)
H12A—C12—H12B107.5C23A—C31C—N27125.4 (3)
C2'—C13—H13A109.5C23A—C31C—C31B126.0 (3)
C2'—C13—H13B109.5N27—C31C—C31B108.6 (3)
H13A—C13—H13B109.5N21'—C32—C30115.1 (3)
C2'—C13—H13C109.5N21'—C32—H32A108.5
H13A—C13—H13C109.5C30—C32—H32A108.5
H13B—C13—H13C109.5N21'—C32—H32B108.5
C2'—N1'—C5'109.9 (4)C30—C32—H32B108.5
C2'—N1'—C12126.2 (3)H32A—C32—H32B107.5
C5'—N1'—C12123.9 (4)C22'—C33—H33A109.5
N1'—C2'—N3'107.8 (4)C22'—C33—H33B109.5
N1'—C2'—C13127.1 (4)H33A—C33—H33B109.5
N3'—C2'—C13125.1 (4)C22'—C33—H33C109.5
C2'—N3'—C4'109.7 (4)H33A—C33—H33C109.5
C2'—N3'—H3'122 (4)H33B—C33—H33C109.5
C4'—N3'—H3'128 (4)C22'—N21'—C25'108.7 (3)
C5'—C4'—N3'106.7 (4)C22'—N21'—C32126.3 (3)
C5'—C4'—H4'126.6C25'—N21'—C32124.9 (3)
N3'—C4'—H4'126.6N21'—C22'—N23'107.7 (3)
C4'—C5'—N1'105.9 (4)N21'—C22'—C33126.7 (4)
C4'—C5'—H5'127.0N23'—C22'—C33125.6 (4)
N1'—C5'—H5'127.0C22'—N23'—C24'109.1 (3)
C22—C21—C31B118.7 (3)C22'—N23'—H23'125 (3)
C22—C21—H21120.6C24'—N23'—H23'125 (3)
C31B—C21—H21120.6C25'—C24'—N23'107.4 (4)
C21—C22—C23121.8 (3)C25'—C24'—H24'126.3
C21—C22—H22119.1N23'—C24'—H24'126.3
C23—C22—H22119.1C24'—C25'—N21'107.1 (4)
C23A—C23—C22121.3 (3)C24'—C25'—H25'126.5
C23A—C23—H23119.3N21'—C25'—H25'126.5
C22—C23—H23119.3H01—O1W—H02106 (5)
C31C—C23A—C23115.2 (3)H03—O2W—H04106 (5)
C11B—C1—C2—C31.5 (6)C22—C23—C23A—C24179.7 (4)
C1—C2—C3—C3A1.5 (6)C31C—C23A—C24—C25"18.0 (9)
C2—C3—C3A—C11C1.4 (6)C23—C23A—C24—C25"160.8 (8)
C2—C3—C3A—C4176.8 (4)C31C—C23A—C24—C2521.6 (5)
C11C—C3A—C4—C524.5 (5)C23—C23A—C24—C25159.5 (4)
C3—C3A—C4—C5157.4 (4)C23A—C24—C25—C2647.0 (6)
C3A—C4—C5—C650.0 (5)C24—C25—C26—N2747.5 (6)
C4—C5—C6—N748.8 (5)C23A—C24—C25"—C2634.9 (16)
C5—C6—N7—C7A160.7 (4)N27—C26—C25"—C2432.9 (15)
C5—C6—N7—C11C23.5 (5)C25—C26—N27—C27A160.0 (4)
C11C—N7—C7A—C11A1.4 (4)C25"—C26—N27—C27A161.2 (8)
C6—N7—C7A—C11A177.5 (4)C25—C26—N27—C31C24.4 (6)
C11C—N7—C7A—C8178.6 (4)C25"—C26—N27—C31C14.4 (9)
C6—N7—C7A—C82.5 (6)C31C—N27—C27A—C31A0.7 (5)
N7—C7A—C8—C9164.4 (4)C26—N27—C27A—C31A176.7 (4)
C11A—C7A—C8—C915.6 (5)C31C—N27—C27A—C28178.6 (4)
C7A—C8—C9—C1045.0 (4)C26—N27—C27A—C282.6 (7)
C8—C9—C10—C1156.1 (4)N27—C27A—C28—C29157.9 (4)
C8—C9—C10—C12178.1 (3)C31A—C27A—C28—C2921.4 (5)
C12—C10—C11—O124.5 (5)C27A—C28—C29—C3047.4 (4)
C9—C10—C11—O1146.9 (3)C28—C29—C30—C32179.5 (3)
C12—C10—C11—C11A157.6 (3)C28—C29—C30—C3153.9 (4)
C9—C10—C11—C11A35.2 (4)C32—C30—C31—O228.7 (5)
N7—C7A—C11A—C11175.7 (3)C29—C30—C31—O2150.6 (3)
C8—C7A—C11A—C114.3 (6)C32—C30—C31—C31A152.7 (3)
N7—C7A—C11A—C11B0.8 (4)C29—C30—C31—C31A30.8 (4)
C8—C7A—C11A—C11B179.2 (3)N27—C27A—C31A—C31179.2 (3)
O1—C11—C11A—C7A176.0 (4)C28—C27A—C31A—C310.2 (6)
C10—C11—C11A—C7A6.1 (5)N27—C27A—C31A—C31B0.1 (5)
O1—C11—C11A—C11B10.4 (6)C28—C27A—C31A—C31B179.2 (4)
C10—C11—C11A—C11B167.5 (4)O2—C31—C31A—C27A176.6 (4)
C2—C1—C11B—C11C1.4 (5)C30—C31—C31A—C27A4.8 (5)
C2—C1—C11B—C11A175.7 (4)O2—C31—C31A—C31B2.1 (6)
C7A—C11A—C11B—C1177.5 (4)C30—C31—C31A—C31B176.4 (4)
C11—C11A—C11B—C13.2 (7)C22—C21—C31B—C31C1.4 (5)
C7A—C11A—C11B—C11C0.1 (4)C22—C21—C31B—C31A177.2 (4)
C11—C11A—C11B—C11C174.2 (4)C27A—C31A—C31B—C31C0.5 (4)
C7A—N7—C11C—C3A175.9 (4)C31—C31A—C31B—C31C178.4 (4)
C6—N7—C11C—C3A0.6 (6)C27A—C31A—C31B—C21179.2 (4)
C7A—N7—C11C—C11B1.5 (4)C31—C31A—C31B—C210.2 (8)
C6—N7—C11C—C11B178.0 (3)C23—C23A—C31C—N27178.4 (4)
C3—C3A—C11C—N7178.4 (4)C24—C23A—C31C—N270.5 (6)
C4—C3A—C11C—N70.0 (6)C23—C23A—C31C—C31B0.8 (6)
C3—C3A—C11C—C11B1.4 (6)C24—C23A—C31C—C31B178.2 (4)
C4—C3A—C11C—C11B176.9 (4)C27A—N27—C31C—C23A177.0 (4)
C1—C11B—C11C—N7178.9 (3)C26—N27—C31C—C23A0.5 (6)
C11A—C11B—C11C—N70.9 (4)C27A—N27—C31C—C31B1.0 (4)
C1—C11B—C11C—C3A1.5 (6)C26—N27—C31C—C31B177.4 (4)
C11A—C11B—C11C—C3A176.5 (4)C21—C31B—C31C—C23A1.9 (6)
C11—C10—C12—N1'59.5 (4)C31A—C31B—C31C—C23A177.0 (4)
C9—C10—C12—N1'176.3 (3)C21—C31B—C31C—N27179.9 (3)
C10—C12—N1'—C2'108.6 (4)C31A—C31B—C31C—N270.9 (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'—C13177.4 (4)C30—C32—N21'—C25'64.6 (5)
C12—N1'—C2'—C131.4 (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'—C33178.9 (3)
C2'—N3'—C4'—C5'0.1 (5)C32—N21'—C22'—C332.6 (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—C230.1 (6)N23'—C24'—C25'—N21'0.1 (5)
C21—C22—C23—C23A1.2 (6)C22'—N21'—C25'—C24'0.4 (4)
C22—C23—C23A—C31C0.8 (6)C32—N21'—C25'—C24'179.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O1Wi0.88 (4)1.85 (4)2.724 (5)170 (5)
N23—H23···O2Wi0.88 (4)1.87 (4)2.741 (5)167 (4)
O1W—H01···Cl20.84 (3)2.28 (3)3.117 (3)173 (5)
O1W—H02···Cl1ii0.84 (3)2.27 (3)3.113 (4)178 (5)
O2W—H03···Cl10.85 (3)2.24 (3)3.076 (3)170 (4)
O2W—H04···Cl20.84 (3)2.26 (3)3.086 (3)165 (5)
C9—H9A···Cl10.992.883.797 (4)154
C12—H12B···Cl10.992.853.775 (4)156
C13—H13B···Cl1iii0.982.913.685 (4)137
C29—H29A···Cl10.992.813.761 (4)161
C32—H32B···Cl10.992.963.887 (4)156
C24—H24···Cl1iii0.952.703.632 (4)167
C12—H12A···Cl2iv0.992.883.528 (4)124
C13—H13C···Cl2iv0.982.853.782 (4)159
C5—H5···Cl20.952.733.507 (4)139
C33—H33C···Cl20.982.733.665 (4)160
C25—H25···Cl2iv0.952.553.438 (4)155
C5—H5A···O1v0.992.623.479 (5)145
C2—H2···O2vi0.952.613.482 (5)152
C25—H25B···O2vii0.992.543.398 (6)145
C3—H3···O2Wv0.952.533.479 (5)173
C23—H23···O1Wvii0.952.673.586 (5)164
Symmetry codes: (i) x+2, y1/2, z+1/2; (ii) x+1, y, z; (iii) x+1, y1/2, z+1/2; (iv) x1, y, z; (v) x1/2, y+1/2, z+1; (vi) x+3/2, y, z+1/2; (vii) x1/2, y+1/2, z.
 

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