The title compound, C19H19ClNO+·ClO4-, was synthesized and characterized by 1H NMR and X-ray diffraction techniques.
Supporting information
CCDC reference: 242361
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.042
- wR factor = 0.107
- Data-to-parameter ratio = 15.9
checkCIF/PLATON results
No syntax errors found
Alert level B
REFLT01_ALERT_1_B The number of symmetry-independent reflections cannot
exceed the total number of reflections measured
Number of symmetry-independent reflections = 4010
Total number of reflections = 3901
PLAT230_ALERT_2_B Hirshfeld Test Diff for C11 - C12 .. 7.90 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for C13 - C14 .. 8.40 su
Alert level C
PLAT021_ALERT_1_C Ratio Unique / Expected Reflections too High ... 1.03
PLAT030_ALERT_1_C _diffrn_reflns_number .LE. _reflns_number_total . ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for O4 - C5 .. 5.13 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C9 - C15 .. 5.85 su
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... Cl2
| Author Response: The perchlorate anion rotates in some extent around Cl2.
So oxygen atoms have higher Ueq compared with Cl2.
|
PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. Cl1 .. 3.34 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact O21 .. C5 .. 2.97 Ang.
0 ALERT level A = In general: serious problem
3 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
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).
2-(4–chlorophenyl)-5-methyl-7,8,9,10-tetrahydro-6
H-
cyclohepta[
e][1,3]oxazolo[3,2-
a]pyridin-11-ium perchlorate
top
Crystal data top
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 |
Data collection top
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 top
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 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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) | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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 | | |