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
CCDC reference: 202994
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean (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
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-1
H-imidazol-1-yl)-methyl]-4
H-pyrido[3,2,1-jk]-carbazol-11(8
H)-one monohydrochloride monohydrate
top
Crystal data top
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) Å3 | Lath, colourless |
Z = 8 | 0.70 × 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 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 top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.058 | H 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 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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3′—H3′···O1Wi | 0.88 (4) | 1.85 (4) | 2.724 (5) | 170 (5) |
N23′—H23′···O2Wi | 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···Cl1ii | 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···Cl1iii | 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′···Cl1iii | 0.95 | 2.70 | 3.632 (4) | 167 |
C12—H12A···Cl2iv | 0.99 | 2.88 | 3.528 (4) | 124 |
C13—H13C···Cl2iv | 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′···Cl2iv | 0.95 | 2.55 | 3.438 (4) | 155 |
C5—H5A···O1v | 0.99 | 2.62 | 3.479 (5) | 145 |
C2—H2···O2vi | 0.95 | 2.61 | 3.482 (5) | 152 |
C25—H25B···O2vii | 0.99 | 2.54 | 3.398 (6) | 145 |
C3—H3···O2Wv | 0.95 | 2.53 | 3.479 (5) | 173 |
C23—H23···O1Wvii | 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. |