Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804012462/fl6103sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804012462/fl61032sup2.hkl |
CCDC reference: 242361
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C19H19ClNO+·ClO4− | F(000) = 856 |
Mr = 412.25 | Dx = 1.442 Mg m−3 |
Monoclinic, P21/c | Melting point: 573 K |
Hall symbol: -P 2ybc | Cu Kα radiation, λ = 1.5418 Å |
a = 7.894 (3) Å | Cell parameters from 25 reflections |
b = 18.492 (3) Å | θ = 33–35° |
c = 13.271 (2) Å | µ = 3.35 mm−1 |
β = 101.46 (2)° | T = 293 K |
V = 1898.6 (8) Å3 | Prism, colourless |
Z = 4 | 0.20 × 0.20 × 0.20 mm |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.004 |
Radiation source: fine–focus sealed tube | θmax = 75.0°, θmin = 4.2° |
Graphite monochromator | h = −9→9 |
non–profiled ω scans | k = 0→23 |
4010 measured reflections | l = 0→16 |
3901 independent reflections | 1 standard reflections every 200 reflections |
3310 reflections with I > 2σ(I) | intensity decay: 4% |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0892P)2] where P = (Fo2 + 2Fc2)/3 |
3901 reflections | (Δ/σ)max = 0.001 |
246 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
Experimental. 1H NMR spectrum was recorded on a Bruker AMX–400. |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.86781 (4) | 0.52453 (3) | 0.07797 (3) | 0.06898 (15) | |
O4 | 0.17048 (11) | 0.47536 (4) | 0.28891 (6) | 0.0436 (2) | |
N1 | 0.01358 (12) | 0.37622 (5) | 0.26746 (7) | 0.0390 (2) | |
C2 | 0.14658 (15) | 0.36759 (7) | 0.21245 (9) | 0.0441 (3) | |
H2 | 0.1656 | 0.3275 | 0.1740 | 0.053* | |
C3 | 0.24131 (15) | 0.42855 (6) | 0.22603 (9) | 0.0416 (3) | |
C5 | 0.03369 (14) | 0.44152 (6) | 0.31243 (8) | 0.0395 (2) | |
C6 | −0.07625 (17) | 0.46718 (7) | 0.37331 (10) | 0.0465 (3) | |
H6 | −0.0635 | 0.5134 | 0.4014 | 0.056* | |
C7 | −0.20462 (16) | 0.42191 (7) | 0.39065 (9) | 0.0461 (3) | |
C8 | −0.22535 (15) | 0.35241 (7) | 0.34296 (9) | 0.0463 (3) | |
C9 | −0.11806 (15) | 0.32975 (7) | 0.28018 (9) | 0.0427 (3) | |
C10 | −0.3221 (2) | 0.44627 (9) | 0.46173 (12) | 0.0631 (4) | |
H10A | −0.2840 | 0.4250 | 0.5284 | 0.095* | |
H10B | −0.4384 | 0.4312 | 0.4341 | 0.095* | |
H10C | −0.3181 | 0.4980 | 0.4677 | 0.095* | |
C11 | −0.3639 (2) | 0.30041 (8) | 0.36231 (13) | 0.0601 (3) | |
H11A | −0.4313 | 0.2845 | 0.2969 | 0.072* | |
H11B | −0.4410 | 0.3256 | 0.3989 | 0.072* | |
C12 | −0.2889 (3) | 0.23431 (11) | 0.42463 (16) | 0.0835 (6) | |
H12A | −0.1955 | 0.2500 | 0.4793 | 0.100* | |
H12B | −0.3779 | 0.2133 | 0.4565 | 0.100* | |
C13 | −0.2212 (3) | 0.17667 (11) | 0.36238 (18) | 0.0860 (6) | |
H13A | −0.1783 | 0.1372 | 0.4086 | 0.103* | |
H13B | −0.3186 | 0.1581 | 0.3128 | 0.103* | |
C14 | −0.0819 (2) | 0.19621 (8) | 0.30499 (14) | 0.0675 (4) | |
H14A | −0.0550 | 0.1540 | 0.2678 | 0.081* | |
H14B | 0.0216 | 0.2092 | 0.3543 | 0.081* | |
C15 | −0.1293 (2) | 0.25860 (8) | 0.22896 (11) | 0.0564 (3) | |
H15A | −0.0523 | 0.2581 | 0.1804 | 0.068* | |
H15B | −0.2462 | 0.2515 | 0.1906 | 0.068* | |
C16 | 0.39450 (14) | 0.45278 (7) | 0.19029 (9) | 0.0420 (3) | |
C17 | 0.47217 (16) | 0.51882 (7) | 0.22247 (10) | 0.0447 (3) | |
H17 | 0.4257 | 0.5480 | 0.2672 | 0.054* | |
C18 | 0.61820 (18) | 0.54115 (7) | 0.18808 (11) | 0.0524 (3) | |
H18 | 0.6709 | 0.5849 | 0.2100 | 0.063* | |
C19 | 0.68460 (15) | 0.49772 (8) | 0.12091 (9) | 0.0477 (3) | |
C20 | 0.60781 (17) | 0.43204 (8) | 0.08811 (10) | 0.0520 (3) | |
H20 | 0.6543 | 0.4035 | 0.0427 | 0.062* | |
C21 | 0.46330 (16) | 0.40891 (7) | 0.12229 (10) | 0.0482 (3) | |
H21 | 0.4121 | 0.3648 | 0.1006 | 0.058* | |
Cl2 | 0.27549 (5) | 0.181340 (18) | 0.06047 (3) | 0.05835 (13) | |
O21 | 0.2643 (3) | 0.14812 (11) | −0.03242 (15) | 0.1139 (5) | |
O22 | 0.2463 (3) | 0.25404 (11) | 0.04550 (16) | 0.1247 (6) | |
O23 | 0.1430 (3) | 0.15310 (11) | 0.10492 (15) | 0.1154 (6) | |
O24 | 0.4455 (3) | 0.16810 (12) | 0.11568 (16) | 0.1191 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0431 (2) | 0.1020 (3) | 0.0675 (2) | −0.00954 (16) | 0.02445 (16) | 0.00796 (18) |
O4 | 0.0388 (4) | 0.0462 (4) | 0.0498 (5) | 0.0000 (3) | 0.0186 (3) | −0.0045 (3) |
N1 | 0.0341 (4) | 0.0471 (5) | 0.0381 (4) | 0.0041 (4) | 0.0127 (4) | −0.0010 (4) |
C2 | 0.0415 (6) | 0.0472 (6) | 0.0484 (6) | 0.0074 (5) | 0.0201 (5) | 0.0000 (5) |
C3 | 0.0381 (6) | 0.0459 (6) | 0.0431 (6) | 0.0088 (4) | 0.0132 (4) | −0.0014 (4) |
C5 | 0.0360 (5) | 0.0467 (6) | 0.0378 (5) | 0.0071 (4) | 0.0126 (4) | 0.0020 (4) |
C6 | 0.0467 (6) | 0.0497 (6) | 0.0479 (6) | 0.0080 (5) | 0.0211 (5) | 0.0002 (5) |
C7 | 0.0415 (6) | 0.0552 (7) | 0.0441 (6) | 0.0119 (5) | 0.0148 (5) | 0.0040 (5) |
C8 | 0.0367 (6) | 0.0584 (7) | 0.0466 (6) | 0.0043 (5) | 0.0150 (5) | 0.0060 (5) |
C9 | 0.0397 (6) | 0.0498 (6) | 0.0405 (5) | 0.0005 (4) | 0.0123 (4) | 0.0020 (4) |
C10 | 0.0594 (8) | 0.0776 (9) | 0.0626 (8) | 0.0030 (7) | 0.0368 (7) | −0.0104 (7) |
C11 | 0.0546 (8) | 0.0598 (8) | 0.0749 (9) | −0.0028 (6) | 0.0343 (7) | 0.0033 (7) |
C12 | 0.0945 (14) | 0.0835 (12) | 0.0861 (12) | 0.0028 (10) | 0.0505 (11) | 0.0177 (9) |
C13 | 0.0966 (14) | 0.0739 (11) | 0.0939 (14) | 0.0047 (10) | 0.0344 (11) | 0.0064 (9) |
C14 | 0.0807 (10) | 0.0474 (7) | 0.0808 (10) | 0.0059 (7) | 0.0317 (9) | 0.0006 (7) |
C15 | 0.0580 (8) | 0.0618 (8) | 0.0541 (7) | −0.0041 (6) | 0.0224 (6) | −0.0060 (6) |
C16 | 0.0322 (5) | 0.0492 (6) | 0.0449 (6) | 0.0065 (4) | 0.0084 (4) | 0.0052 (5) |
C17 | 0.0396 (6) | 0.0494 (6) | 0.0479 (6) | 0.0053 (5) | 0.0151 (5) | 0.0003 (5) |
C18 | 0.0454 (7) | 0.0528 (7) | 0.0611 (7) | −0.0050 (5) | 0.0158 (6) | −0.0001 (6) |
C19 | 0.0317 (5) | 0.0682 (8) | 0.0453 (6) | −0.0002 (5) | 0.0124 (5) | 0.0075 (5) |
C20 | 0.0439 (6) | 0.0650 (8) | 0.0509 (7) | 0.0033 (6) | 0.0185 (5) | −0.0053 (6) |
C21 | 0.0438 (6) | 0.0524 (7) | 0.0509 (6) | −0.0008 (5) | 0.0157 (5) | −0.0051 (5) |
Cl2 | 0.0605 (2) | 0.0551 (2) | 0.0608 (2) | 0.00105 (13) | 0.01539 (16) | −0.00297 (13) |
O21 | 0.1156 (13) | 0.1140 (13) | 0.1132 (12) | 0.0003 (10) | 0.0259 (10) | −0.0127 (10) |
O22 | 0.1493 (18) | 0.1004 (12) | 0.1267 (14) | −0.0064 (11) | 0.0333 (13) | −0.0066 (10) |
O23 | 0.1184 (14) | 0.1116 (13) | 0.1256 (14) | 0.0025 (11) | 0.0472 (11) | 0.0062 (10) |
O24 | 0.1067 (13) | 0.1331 (16) | 0.1135 (13) | 0.0039 (10) | 0.0124 (11) | 0.0062 (10) |
Cl1—C19 | 1.729 (1) | C12—H12A | 0.9700 |
O4—C5 | 1.337 (1) | C12—H12B | 0.9700 |
O4—C3 | 1.394 (1) | C13—C14 | 1.501 (3) |
N1—C5 | 1.342 (1) | C13—H13A | 0.9700 |
N1—C9 | 1.384 (1) | C13—H13B | 0.9700 |
N1—C2 | 1.402 (1) | C14—C15 | 1.529 (2) |
C2—C3 | 1.345 (2) | C14—H14A | 0.9700 |
C2—H2 | 0.9300 | C14—H14B | 0.9700 |
C3—C16 | 1.455 (2) | C15—H15A | 0.9700 |
C5—C6 | 1.382 (2) | C15—H15B | 0.9700 |
C6—C7 | 1.369 (2) | C16—C17 | 1.3949 (18) |
C6—H6 | 0.9300 | C16—C21 | 1.4008 (17) |
C7—C8 | 1.427 (2) | C17—C18 | 1.3844 (18) |
C7—C10 | 1.517 (2) | C17—H17 | 0.9300 |
C8—C9 | 1.367 (2) | C18—C19 | 1.3785 (19) |
C8—C11 | 1.516 (2) | C18—H18 | 0.9300 |
C9—C15 | 1.476 (2) | C19—C20 | 1.388 (2) |
C10—H10A | 0.9600 | C20—C21 | 1.3769 (18) |
C10—H10B | 0.9600 | C20—H20 | 0.9300 |
C10—H10C | 0.9600 | C21—H21 | 0.9300 |
C11—C12 | 1.528 (3) | Cl2—O21 | 1.364 (2) |
C11—H11A | 0.9700 | Cl2—O22 | 1.372 (2) |
C11—H11B | 0.9700 | Cl2—O23 | 1.400 (2) |
C12—C13 | 1.510 (3) | Cl2—O24 | 1.417 (2) |
C5—O4—C3 | 106.7 (1) | C14—C13—C12 | 118.85 (17) |
C5—N1—C9 | 122.0 (1) | C14—C13—H13A | 107.6 |
C5—N1—C2 | 107.4 (1) | C12—C13—H13A | 107.6 |
C9—N1—C2 | 130.6 (1) | C14—C13—H13B | 107.6 |
C3—C2—N1 | 106.8 (1) | C12—C13—H13B | 107.6 |
C3—C2—H2 | 126.6 | H13A—C13—H13B | 107.0 |
N1—C2—H2 | 126.6 | C13—C14—C15 | 114.09 (15) |
C2—C3—O4 | 108.8 (1) | C13—C14—H14A | 108.7 |
C2—C3—C16 | 133.7 (1) | C15—C14—H14A | 108.7 |
O4—C3—C16 | 117.5 (1) | C13—C14—H14B | 108.7 |
O4—C5—N1 | 110.3 (1) | C15—C14—H14B | 108.7 |
O4—C5—C6 | 127.3 (1) | H14A—C14—H14B | 107.6 |
N1—C5—C6 | 122.4 (1) | C9—C15—C14 | 112.61 (12) |
C7—C6—C5 | 117.4 (1) | C9—C15—H15A | 109.1 |
C7—C6—H6 | 121.3 | C14—C15—H15A | 109.1 |
C5—C6—H6 | 121.3 | C9—C15—H15B | 109.1 |
C6—C7—C8 | 120.0 (1) | C14—C15—H15B | 109.1 |
C6—C7—C10 | 119.2 (1) | H15A—C15—H15B | 107.8 |
C8—C7—C10 | 120.9 (1) | C17—C16—C21 | 120.08 (11) |
C9—C8—C7 | 121.1 (1) | C17—C16—C3 | 120.87 (11) |
C9—C8—C11 | 117.6 (1) | C21—C16—C3 | 119.05 (11) |
C7—C8—C11 | 121.3 (1) | C18—C17—C16 | 120.29 (11) |
C8—C9—N1 | 117.1 (1) | C18—C17—H17 | 119.9 |
C8—C9—C15 | 124.5 (1) | C16—C17—H17 | 119.9 |
N1—C9—C15 | 118.4 (1) | C19—C18—C17 | 119.20 (12) |
C7—C10—H10A | 109.5 | C19—C18—H18 | 120.4 |
C7—C10—H10B | 109.5 | C17—C18—H18 | 120.4 |
H10A—C10—H10B | 109.5 | C18—C19—C20 | 120.94 (11) |
C7—C10—H10C | 109.5 | C18—C19—Cl1 | 119.76 (11) |
H10A—C10—H10C | 109.5 | C20—C19—Cl1 | 119.29 (10) |
H10B—C10—H10C | 109.5 | C21—C20—C19 | 120.48 (12) |
C8—C11—C12 | 112.6 (1) | C21—C20—H20 | 119.8 |
C8—C11—H11A | 109.1 | C19—C20—H20 | 119.8 |
C12—C11—H11A | 109.1 | C20—C21—C16 | 119.01 (12) |
C8—C11—H11B | 109.1 | C20—C21—H21 | 120.5 |
C12—C11—H11B | 109.1 | C16—C21—H21 | 120.5 |
H11A—C11—H11B | 107.8 | O21—Cl2—O22 | 109.36 (12) |
C13—C12—C11 | 114.19 (16) | O21—Cl2—O23 | 107.03 (12) |
C13—C12—H12A | 108.7 | O22—Cl2—O23 | 107.98 (13) |
C11—C12—H12A | 108.7 | O21—Cl2—O24 | 105.92 (12) |
C13—C12—H12B | 108.7 | O22—Cl2—O24 | 111.02 (13) |
C11—C12—H12B | 108.7 | O23—Cl2—O24 | 115.34 (13) |
H12A—C12—H12B | 107.6 |