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The title compound, C18H20N+·Cl-·H2O, contains a tetraalkylammonium chloride functionality bound to an anthryl moiety. There are two formula units in the asymmetric unit of the crystal structure, with a dihedral angle of 22.55 (1)° between the anthryl planes.
Supporting information
CCDC reference: 214862
Key indicators
- Single-crystal X-ray study
- T = 148 K
- Mean (C-C) = 0.008 Å
- R factor = 0.044
- wR factor = 0.054
- Data-to-parameter ratio = 8.3
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.800 0.970
Tmin' and Tmax expected: 0.946 0.972
RR' = 0.847
Please check that your absorption correction is appropriate.
THETM_01 Alert C The value of sine(theta_max)/wavelength is less than 0.590
Calculated sin(theta_max)/wavelength = 0.5884
PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . CL1
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 24.72
From the CIF: _reflns_number_total 4282
Count of symmetry unique reflns 2932
Completeness (_total/calc) 146.04%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1350
Fraction of Friedel pairs measured 0.460
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
3 Alert Level C = Please check
The synthesis of (I) has been described in the literature (Takagi, 1983). Suitable crystals were obtained by slow evaporation of a saturated solution of (I) in wet acetonitrile. The water H atoms were located in the difference Fourier map and their postitions were refined. All other H atoms were calculated geometrically and not refined. Assignment of the correct enantiomorph was accomplished by comparison of the intensities of Friedel pairs of reflections. The correct enantiomorph of the space group is shown in Fig. 1.
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1992); program(s) used to refine structure: TEXSAN; molecular graphics: TEXSAN; software used to prepare material for publication: TEXSAN.
Crystal data top
C18H20N+·Cl−·H2O | F(000) = 648.00 |
Mr = 303.83 | Dx = 1.249 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.7107 Å |
a = 8.1368 (6) Å | Cell parameters from 3212 reflections |
b = 10.2645 (8) Å | θ = 2.5–24.3° |
c = 19.351 (2) Å | µ = 0.24 mm−1 |
β = 92.088 (1)° | T = 148 K |
V = 1615.1 (2) Å3 | Tablet, yellow |
Z = 4 | 0.23 × 0.15 × 0.12 mm |
Data collection top
SMART 1K CCD diffractometer | 4282 independent reflections |
Radiation source: X-ray tube | 3143 reflections with F2 > 3σ(F2) |
Graphite monochromator | Rint = 0.057 |
ω scans | θmax = 24.7°, θmin = 2.5° |
Absorption correction: empirical (using intensity measurements) (Blessing, 1995) | h = −9→8 |
Tmin = 0.80, Tmax = 0.97 | k = −11→10 |
7199 measured reflections | l = −22→22 |
Refinement top
Refinement on F | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.044 | Weighting scheme based on measured s.u.'s |
wR(F2) = 0.054 | (Δ/σ)max = 0.007 |
S = 1.54 | Δρmax = 0.70 e Å−3 |
3143 reflections | Δρmin = −0.26 e Å−3 |
378 parameters | |
Crystal data top
C18H20N+·Cl−·H2O | V = 1615.1 (2) Å3 |
Mr = 303.83 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 8.1368 (6) Å | µ = 0.24 mm−1 |
b = 10.2645 (8) Å | T = 148 K |
c = 19.351 (2) Å | 0.23 × 0.15 × 0.12 mm |
β = 92.088 (1)° | |
Data collection top
SMART 1K CCD diffractometer | 4282 independent reflections |
Absorption correction: empirical (using intensity measurements) (Blessing, 1995) | 3143 reflections with F2 > 3σ(F2) |
Tmin = 0.80, Tmax = 0.97 | Rint = 0.057 |
7199 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.54 | Δρmax = 0.70 e Å−3 |
3143 reflections | Δρmin = −0.26 e Å−3 |
378 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | −0.8729 (2) | −0.4608 | 0.01010 (7) | 0.0317 (4) | |
Cl2 | −0.3544 (2) | −0.5452 (2) | −0.48686 (7) | 0.0313 (4) | |
O1 | −1.1640 (5) | −0.2587 (5) | 0.0326 (3) | 0.072 (2) | |
O2 | −0.3419 (4) | −0.8532 (4) | −0.5084 (2) | 0.042 (1) | |
N1 | −0.6536 (5) | −0.1345 (5) | −0.0504 (2) | 0.015 (1) | |
N2 | −0.1511 (4) | −0.1949 (4) | −0.4454 (2) | 0.020 (1) | |
C1 | −0.7789 (5) | −0.1706 (5) | −0.1725 (2) | 0.027 (1) | |
C2 | −0.7310 (6) | −0.2876 (5) | −0.2058 (2) | 0.014 (1) | |
C3 | −0.7174 (6) | −0.4108 (6) | −0.1715 (3) | 0.022 (2) | |
C4 | −0.6697 (7) | −0.5203 (5) | −0.2061 (3) | 0.030 (2) | |
C5 | −0.6338 (7) | −0.5128 (6) | −0.2771 (3) | 0.036 (2) | |
C6 | −0.6475 (7) | −0.3996 (7) | −0.3117 (3) | 0.030 (2) | |
C7 | −0.6967 (6) | −0.2831 (6) | −0.2779 (3) | 0.021 (2) | |
C8 | −0.7114 (6) | −0.1665 (6) | −0.3142 (2) | 0.018 (2) | |
C9 | −0.7655 (6) | −0.0540 (6) | −0.2826 (2) | 0.022 (1) | |
C10 | −0.7884 (6) | 0.0645 (6) | −0.3216 (3) | 0.022 (2) | |
C11 | −0.8482 (7) | 0.1723 (6) | −0.2925 (3) | 0.030 (2) | |
C12 | −0.8874 (6) | 0.1709 (6) | −0.2223 (3) | 0.039 (2) | |
C13 | −0.8671 (6) | 0.0627 (5) | −0.1832 (2) | 0.022 (2) | |
C14 | −0.8034 (5) | −0.0554 (6) | −0.2111 (2) | 0.019 (1) | |
C15 | −0.8060 (5) | −0.1706 (5) | −0.0958 (2) | 0.018 (1) | |
C16 | −0.5764 (6) | −0.0094 (5) | −0.0707 (3) | 0.032 (2) | |
C17 | −0.7066 (7) | −0.1240 (6) | 0.0226 (3) | 0.028 (2) | |
C18 | −0.5271 (6) | −0.2408 (5) | −0.0539 (3) | 0.018 (2) | |
C19 | −0.2742 (5) | −0.1882 (6) | −0.3243 (2) | 0.017 (1) | |
C20 | −0.3007 (6) | −0.0623 (5) | −0.2971 (2) | 0.022 (1) | |
C21 | −0.3583 (6) | 0.0449 (6) | −0.3389 (2) | 0.024 (2) | |
C22 | −0.3825 (7) | 0.1656 (6) | −0.3106 (3) | 0.028 (2) | |
C23 | −0.3581 (6) | 0.1857 (6) | −0.2388 (3) | 0.025 (2) | |
C24 | −0.3038 (7) | 0.0875 (6) | −0.1968 (3) | 0.022 (2) | |
C25 | −0.2765 (6) | −0.0394 (6) | −0.2248 (2) | 0.023 (1) | |
C26 | −0.2247 (6) | −0.1398 (6) | −0.1814 (2) | 0.030 (2) | |
C27 | −0.2019 (6) | −0.2662 (5) | −0.2057 (2) | 0.017 (2) | |
C28 | −0.1522 (6) | −0.3686 (6) | −0.1603 (3) | 0.038 (2) | |
C29 | −0.1259 (7) | −0.4893 (6) | −0.1845 (3) | 0.032 (2) | |
C30 | −0.1535 (7) | −0.5175 (5) | −0.2552 (3) | 0.034 (2) | |
C31 | −0.2037 (6) | −0.4235 (6) | −0.3002 (3) | 0.017 (2) | |
C32 | −0.2261 (6) | −0.2920 (5) | −0.2789 (2) | 0.009 (1) | |
C33 | −0.3010 (5) | −0.2135 (5) | −0.4006 (2) | 0.017 (1) | |
C34 | −0.0254 (6) | −0.2980 (5) | −0.4307 (3) | 0.028 (2) | |
C35 | −0.2098 (7) | −0.2058 (6) | −0.5197 (2) | 0.047 (2) | |
C36 | −0.0711 (6) | −0.0654 (6) | −0.4348 (2) | 0.027 (2) | |
H1 | −0.7416 | −0.4167 | −0.1239 | 0.0259 | |
H2 | −0.6611 | −0.6011 | −0.1824 | 0.0360 | |
H3 | −0.5994 | −0.5886 | −0.3006 | 0.0427 | |
H4 | −0.6242 | −0.3970 | −0.3595 | 0.0356 | |
H5 | −0.6833 | −0.1634 | −0.3615 | 0.0210 | |
H6 | −0.7599 | 0.0664 | −0.3688 | 0.0268 | |
H7 | −0.8648 | 0.2496 | −0.3193 | 0.0357 | |
H8 | −0.9288 | 0.2481 | −0.2019 | 0.0471 | |
H9 | −0.8959 | 0.0652 | −0.1361 | 0.0262 | |
H10 | −0.8907 | −0.1097 | −0.0867 | 0.0217 | |
H11 | −0.8404 | −0.2553 | −0.0829 | 0.0217 | |
H12 | −0.5388 | −0.0163 | −0.1165 | 0.0389 | |
H13 | −0.4859 | 0.0095 | −0.0399 | 0.0389 | |
H14 | −0.6550 | 0.0590 | −0.0688 | 0.0389 | |
H15 | −0.7836 | −0.0549 | 0.0260 | 0.0336 | |
H16 | −0.6135 | −0.1069 | 0.0522 | 0.0336 | |
H17 | −0.7562 | −0.2035 | 0.0357 | 0.0336 | |
H18 | −0.5744 | −0.3210 | −0.0407 | 0.0214 | |
H19 | −0.4364 | −0.2207 | −0.0233 | 0.0214 | |
H20 | −0.4902 | −0.2473 | −0.0998 | 0.0214 | |
H21 | −0.3804 | 0.0322 | −0.3868 | 0.0283 | |
H22 | −0.4158 | 0.2366 | −0.3396 | 0.0337 | |
H23 | −0.3801 | 0.2691 | −0.2197 | 0.0305 | |
H24 | −0.2844 | 0.1032 | −0.1487 | 0.0266 | |
H25 | −0.2041 | −0.1220 | −0.1337 | 0.0362 | |
H26 | −0.1371 | −0.3515 | −0.1122 | 0.0461 | |
H27 | −0.0883 | −0.5556 | −0.1537 | 0.0388 | |
H28 | −0.1370 | −0.6035 | −0.2715 | 0.0407 | |
H29 | −0.2246 | −0.4455 | −0.3473 | 0.0200 | |
H30 | −0.3373 | −0.3008 | −0.4059 | 0.0209 | |
H31 | −0.3849 | −0.1558 | −0.4172 | 0.0209 | |
H32 | −0.0744 | −0.3812 | −0.4367 | 0.0338 | |
H33 | 0.0166 | −0.2891 | −0.3845 | 0.0338 | |
H34 | 0.0620 | −0.2887 | −0.4616 | 0.0338 | |
H35 | −0.2866 | −0.1381 | −0.5302 | 0.0569 | |
H36 | −0.2611 | −0.2878 | −0.5270 | 0.0569 | |
H37 | −0.1188 | −0.1979 | −0.5488 | 0.0569 | |
H38 | 0.0166 | −0.0562 | −0.4656 | 0.0322 | |
H39 | −0.0290 | −0.0585 | −0.3885 | 0.0322 | |
H40 | −0.1495 | 0.0019 | −0.4436 | 0.0322 | |
H41 | −0.4565 | −0.9074 | −0.5019 | 0.0592 | |
H42 | −0.3636 | −0.7705 | −0.4995 | 0.0592 | |
H43 | −1.0685 | −0.2843 | 0.0273 | 0.0592 | |
H44 | −1.1298 | −0.1784 | 0.0028 | 0.0592 | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0449 (9) | 0.045 (1) | 0.0363 (8) | −0.0122 (7) | −0.0028 (7) | 0.0137 (7) |
Cl2 | 0.0409 (8) | 0.0380 (10) | 0.0464 (8) | −0.0033 (8) | 0.0019 (7) | −0.0083 (8) |
O1 | 0.030 (2) | 0.091 (4) | 0.105 (4) | −0.003 (2) | 0.004 (2) | 0.051 (3) |
O2 | 0.032 (2) | 0.045 (3) | 0.049 (2) | 0.005 (2) | 0.005 (2) | 0.006 (2) |
N1 | 0.025 (2) | 0.030 (3) | 0.020 (2) | −0.005 (2) | −0.005 (2) | 0.001 (2) |
N2 | 0.022 (2) | 0.026 (3) | 0.024 (2) | 0.002 (2) | 0.006 (2) | −0.004 (2) |
C1 | 0.018 (3) | 0.023 (3) | 0.020 (3) | −0.002 (2) | 0.003 (2) | −0.003 (2) |
C2 | 0.019 (3) | 0.023 (3) | 0.028 (3) | 0.000 (2) | −0.003 (2) | −0.002 (2) |
C3 | 0.027 (3) | 0.023 (3) | 0.038 (3) | 0.001 (3) | −0.002 (2) | 0.001 (3) |
C4 | 0.028 (3) | 0.019 (4) | 0.055 (4) | 0.004 (3) | −0.001 (3) | −0.004 (3) |
C5 | 0.028 (3) | 0.027 (4) | 0.065 (4) | 0.006 (3) | 0.008 (3) | −0.017 (3) |
C6 | 0.027 (3) | 0.045 (4) | 0.040 (4) | 0.003 (3) | 0.004 (3) | −0.018 (3) |
C7 | 0.020 (3) | 0.029 (4) | 0.030 (3) | −0.002 (2) | −0.001 (2) | −0.007 (3) |
C8 | 0.025 (3) | 0.046 (4) | 0.018 (3) | −0.005 (3) | 0.000 (2) | 0.000 (3) |
C9 | 0.023 (3) | 0.024 (3) | 0.023 (3) | −0.007 (3) | −0.001 (2) | 0.002 (3) |
C10 | 0.033 (3) | 0.042 (4) | 0.029 (3) | −0.012 (3) | −0.008 (2) | 0.010 (3) |
C11 | 0.041 (4) | 0.027 (4) | 0.039 (4) | −0.005 (3) | −0.009 (3) | 0.013 (3) |
C12 | 0.028 (3) | 0.026 (4) | 0.042 (4) | 0.004 (3) | −0.008 (3) | 0.000 (3) |
C13 | 0.028 (3) | 0.027 (4) | 0.030 (3) | 0.004 (3) | 0.000 (2) | −0.002 (3) |
C14 | 0.015 (2) | 0.023 (3) | 0.027 (3) | −0.002 (2) | −0.004 (2) | 0.002 (2) |
C15 | 0.016 (2) | 0.021 (3) | 0.034 (3) | 0.001 (2) | −0.001 (2) | 0.000 (2) |
C16 | 0.032 (3) | 0.036 (4) | 0.029 (3) | −0.005 (3) | −0.007 (2) | −0.002 (2) |
C17 | 0.036 (3) | 0.047 (4) | 0.025 (3) | −0.004 (3) | 0.001 (2) | −0.005 (3) |
C18 | 0.031 (3) | 0.030 (4) | 0.037 (3) | 0.007 (3) | −0.008 (2) | 0.003 (2) |
C19 | 0.016 (3) | 0.024 (3) | 0.025 (3) | −0.002 (2) | 0.002 (2) | 0.001 (2) |
C20 | 0.018 (3) | 0.025 (3) | 0.028 (3) | 0.000 (2) | 0.004 (2) | 0.002 (3) |
C21 | 0.030 (3) | 0.029 (4) | 0.024 (3) | 0.007 (3) | 0.003 (2) | −0.003 (3) |
C22 | 0.040 (4) | 0.022 (4) | 0.039 (3) | 0.006 (3) | 0.009 (3) | 0.005 (3) |
C23 | 0.027 (3) | 0.025 (4) | 0.045 (4) | 0.002 (3) | 0.013 (3) | −0.005 (3) |
C24 | 0.036 (3) | 0.031 (4) | 0.028 (3) | −0.009 (3) | 0.005 (2) | −0.009 (3) |
C25 | 0.019 (2) | 0.024 (3) | 0.028 (3) | −0.004 (3) | 0.004 (2) | 0.001 (3) |
C26 | 0.025 (3) | 0.034 (4) | 0.023 (3) | −0.007 (3) | 0.001 (2) | −0.005 (3) |
C27 | 0.017 (3) | 0.030 (4) | 0.027 (3) | 0.001 (2) | −0.001 (2) | 0.003 (3) |
C28 | 0.026 (3) | 0.032 (4) | 0.037 (3) | −0.005 (3) | 0.002 (3) | 0.007 (3) |
C29 | 0.031 (3) | 0.041 (4) | 0.042 (3) | 0.008 (3) | 0.007 (3) | 0.014 (3) |
C30 | 0.032 (3) | 0.018 (4) | 0.045 (3) | 0.003 (3) | 0.007 (3) | 0.004 (3) |
C31 | 0.025 (3) | 0.030 (4) | 0.033 (3) | −0.004 (3) | 0.004 (2) | −0.002 (3) |
C32 | 0.019 (3) | 0.025 (3) | 0.026 (3) | −0.001 (2) | 0.004 (2) | −0.002 (2) |
C33 | 0.022 (3) | 0.022 (3) | 0.025 (3) | 0.000 (2) | 0.005 (2) | −0.003 (2) |
C34 | 0.033 (3) | 0.025 (3) | 0.039 (3) | 0.006 (3) | 0.006 (2) | −0.006 (3) |
C35 | 0.053 (4) | 0.049 (4) | 0.020 (3) | 0.002 (3) | 0.003 (3) | −0.006 (3) |
C36 | 0.024 (3) | 0.031 (4) | 0.036 (3) | −0.002 (3) | 0.004 (2) | −0.002 (3) |
Geometric parameters (Å, º) top
N1—C15 | 1.539 (6) | O1—H44 | 1.0494 (1) |
N1—C16 | 1.488 (6) | O2—H41 | 1.0967 (1) |
N1—C17 | 1.495 (6) | O2—H42 | 0.8857 (1) |
N1—C18 | 1.503 (6) | C3—H1 | 0.9500 (1) |
N2—C33 | 1.535 (6) | C4—H2 | 0.9500 (1) |
N2—C34 | 1.492 (7) | C5—H3 | 0.9500 (1) |
N2—C35 | 1.503 (6) | C6—H4 | 0.9500 (1) |
N2—C36 | 1.490 (7) | C8—H5 | 0.9500 (1) |
C1—C2 | 1.423 (7) | C10—H6 | 0.9500 (1) |
C1—C14 | 1.408 (7) | C11—H7 | 0.9500 (1) |
C1—C15 | 1.510 (6) | C12—H8 | 0.9500 (1) |
C2—C3 | 1.430 (7) | C13—H9 | 0.9500 (1) |
C2—C7 | 1.434 (7) | C15—H10 | 0.9500 (1) |
C3—C4 | 1.372 (7) | C15—H11 | 0.9500 (1) |
C4—C5 | 1.418 (8) | C16—H12 | 0.9500 (1) |
C5—C6 | 1.343 (8) | C16—H13 | 0.9500 (1) |
C6—C7 | 1.428 (8) | C16—H14 | 0.9500 (1) |
C7—C8 | 1.391 (7) | C17—H15 | 0.9500 (1) |
C8—C9 | 1.387 (7) | C17—H16 | 0.9500 (1) |
C9—C10 | 1.440 (8) | C17—H17 | 0.9500 (1) |
C9—C14 | 1.427 (6) | C18—H18 | 0.9500 (1) |
C10—C11 | 1.341 (8) | C18—H19 | 0.9500 (1) |
C11—C12 | 1.407 (7) | C18—H20 | 0.9500 (1) |
C12—C13 | 1.350 (7) | C21—H21 | 0.9500 (1) |
C13—C14 | 1.432 (7) | C22—H22 | 0.9500 (1) |
C19—C20 | 1.416 (7) | C23—H23 | 0.9500 (1) |
C19—C32 | 1.427 (7) | C24—H24 | 0.9500 (1) |
C19—C33 | 1.505 (7) | C26—H25 | 0.9500 (1) |
C20—C21 | 1.434 (7) | C28—H26 | 0.9500 (1) |
C20—C25 | 1.424 (7) | C29—H27 | 0.9500 (1) |
C21—C22 | 1.371 (8) | C30—H28 | 0.9500 (1) |
C22—C23 | 1.412 (7) | C31—H29 | 0.9500 (1) |
C23—C24 | 1.359 (8) | C33—H30 | 0.9500 (1) |
C24—C25 | 1.431 (7) | C33—H31 | 0.9500 (1) |
C25—C26 | 1.385 (7) | C34—H32 | 0.9500 (1) |
C26—C27 | 1.395 (7) | C34—H33 | 0.9500 (1) |
C27—C28 | 1.419 (7) | C34—H34 | 0.9500 (1) |
C27—C32 | 1.447 (7) | C35—H35 | 0.9500 (1) |
C28—C29 | 1.344 (8) | C35—H36 | 0.9500 (1) |
C29—C30 | 1.409 (8) | C35—H37 | 0.9500 (1) |
C30—C31 | 1.352 (7) | C36—H38 | 0.9500 (1) |
C31—C32 | 1.425 (7) | C36—H39 | 0.9500 (1) |
O1—H43 | 0.8304 (1) | C36—H40 | 0.9500 (1) |
| | | |
C15—N1—C16 | 113.4 (3) | C11—C12—C13 | 121.5 (5) |
C15—N1—C17 | 107.6 (3) | C12—C13—C14 | 121.6 (5) |
C15—N1—C18 | 109.8 (4) | C1—C14—C9 | 119.3 (5) |
C16—N1—C17 | 109.0 (4) | C1—C14—C13 | 123.9 (4) |
C16—N1—C18 | 108.5 (4) | C9—C14—C13 | 116.8 (5) |
C17—N1—C18 | 108.4 (4) | N1—C15—C1 | 114.7 (3) |
C33—N2—C34 | 110.9 (4) | C20—C19—C32 | 119.6 (4) |
C33—N2—C35 | 107.5 (4) | C20—C19—C33 | 120.3 (4) |
C33—N2—C36 | 112.7 (4) | C32—C19—C33 | 120.1 (5) |
C34—N2—C35 | 108.7 (4) | C19—C20—C21 | 122.8 (4) |
C34—N2—C36 | 108.2 (4) | C19—C20—C25 | 119.9 (5) |
C35—N2—C36 | 108.7 (4) | C21—C20—C25 | 117.2 (5) |
C2—C1—C14 | 120.3 (4) | C20—C21—C22 | 121.1 (5) |
C2—C1—C15 | 119.8 (4) | C21—C22—C23 | 120.5 (5) |
C14—C1—C15 | 119.9 (4) | C22—C23—C24 | 120.7 (5) |
C1—C2—C3 | 123.7 (4) | C23—C24—C25 | 120.0 (5) |
C1—C2—C7 | 118.6 (5) | C20—C25—C24 | 120.3 (5) |
C3—C2—C7 | 117.7 (5) | C20—C25—C26 | 120.1 (5) |
C2—C3—C4 | 121.1 (5) | C24—C25—C26 | 119.6 (5) |
C3—C4—C5 | 120.0 (5) | C25—C26—C27 | 121.9 (5) |
C4—C5—C6 | 120.9 (5) | C26—C27—C28 | 121.3 (5) |
C5—C6—C7 | 121.1 (5) | C26—C27—C32 | 119.0 (5) |
C2—C7—C6 | 119.1 (5) | C28—C27—C32 | 119.7 (5) |
C2—C7—C8 | 120.2 (5) | C27—C28—C29 | 120.8 (5) |
C6—C7—C8 | 120.7 (5) | C28—C29—C30 | 120.4 (5) |
C7—C8—C9 | 121.1 (5) | C29—C30—C31 | 120.8 (5) |
C8—C9—C10 | 120.6 (5) | C30—C31—C32 | 122.0 (5) |
C8—C9—C14 | 120.2 (5) | C19—C32—C27 | 119.4 (5) |
C10—C9—C14 | 119.2 (5) | C19—C32—C31 | 124.4 (4) |
C9—C10—C11 | 121.3 (5) | C27—C32—C31 | 116.2 (5) |
C10—C11—C12 | 119.6 (5) | N2—C33—C19 | 116.3 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H43···Cl1 | 0.83 | 2.44 | 3.190 (5) | 150 |
O1—H44···Cl1i | 1.05 | 2.25 | 3.185 (5) | 148 |
O2—H41···Cl2ii | 1.10 | 2.10 | 3.159 (4) | 163 |
O2—H42···Cl2 | 0.89 | 2.33 | 3.191 (5) | 165 |
Symmetry codes: (i) −x−2, y+1/2, −z; (ii) −x−1, y−1/2, −z−1. |
Experimental details
Crystal data |
Chemical formula | C18H20N+·Cl−·H2O |
Mr | 303.83 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 148 |
a, b, c (Å) | 8.1368 (6), 10.2645 (8), 19.351 (2) |
β (°) | 92.088 (1) |
V (Å3) | 1615.1 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.23 × 0.15 × 0.12 |
|
Data collection |
Diffractometer | SMART 1K CCD diffractometer |
Absorption correction | Empirical (using intensity measurements) (Blessing, 1995) |
Tmin, Tmax | 0.80, 0.97 |
No. of measured, independent and observed [F2 > 3σ(F2)] reflections | 7199, 4282, 3143 |
Rint | 0.057 |
(sin θ/λ)max (Å−1) | 0.588 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.054, 1.54 |
No. of reflections | 3143 |
No. of parameters | 378 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.70, −0.26 |
Selected geometric parameters (Å, º) topN1—C15 | 1.539 (6) | N2—C33 | 1.535 (6) |
N1—C16 | 1.488 (6) | N2—C34 | 1.492 (7) |
N1—C17 | 1.495 (6) | N2—C35 | 1.503 (6) |
N1—C18 | 1.503 (6) | N2—C36 | 1.490 (7) |
| | | |
C15—N1—C16 | 113.4 (3) | C33—N2—C35 | 107.5 (4) |
C15—N1—C17 | 107.6 (3) | C33—N2—C36 | 112.7 (4) |
C15—N1—C18 | 109.8 (4) | C34—N2—C35 | 108.7 (4) |
C16—N1—C17 | 109.0 (4) | C34—N2—C36 | 108.2 (4) |
C16—N1—C18 | 108.5 (4) | C35—N2—C36 | 108.7 (4) |
C17—N1—C18 | 108.4 (4) | N1—C15—C1 | 114.7 (3) |
C33—N2—C34 | 110.9 (4) | N2—C33—C19 | 116.3 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H43···Cl1 | 0.83 | 2.44 | 3.190 (5) | 150 |
O1—H44···Cl1i | 1.05 | 2.25 | 3.185 (5) | 148 |
O2—H41···Cl2ii | 1.10 | 2.10 | 3.159 (4) | 163 |
O2—H42···Cl2 | 0.89 | 2.33 | 3.191 (5) | 165 |
Symmetry codes: (i) −x−2, y+1/2, −z; (ii) −x−1, y−1/2, −z−1. |
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The behavior of anthracene and its derivatives plays a large role in many areas of chemistry including nanoscience (Zhang et al., 2003), organometallic chemistry (Carano et al., 2001), asymmetric organic synthesis (Corey et al., 1997), and biochemical probes (Ihmels et al., 2000; Becker & Norden, 2000). The title compound, (I), has been synthesized from the substitution reaction of trimethyl amine and 9-(chloromethyl)anthracene (Takagi et al., 1983) and recrystallized from acetonitrile.
The compound crystallizes with two molecules of (I) in the asymmetric unit. The cationic N atoms have tetrahedral geometry and form ion pairs with the chloride counter-ions. The N···Cl distances (N1···Cl1 = 3.99 Å and N2···Cl2 = 4.03 Å) are consistent with reported values in similar compounds (for a recent example, see Corey et al., 1997). Each chloride ion is hydrogen bonded to two water molecules, one in the asymmetric unit and one symmetry-related water molecule with distances Cl1···O1 = 3.191 (5) Å, Cl1···O1' = 3.178 (6) Å, Cl2···O2 = 3.190 (5) Å and Cl2···O2'' = 3.158 (4) Å.
The closest contact between the two anthryl moieties within the asymmetric unit is C3···C29 of 3.427 (8) Å. The dihedral angle between anthracene planes is 22.55°, indicative of little or no π-stacking. A similar anthracene derivative has been reported (Le Magueres et al., 2000). This previously reported structure exhibits a dihedral angle between layers (23°) that is similar to that observed here between molecules.