Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805000899/kp6027sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805000899/kp6027Isup2.hkl |
CCDC reference: 263706
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.042
- wR factor = 0.116
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293 PLAT480_ALERT_4_C Long H...A H-Bond Reported H9 .. O1 .. 2.69 Ang. PLAT748_ALERT_1_C D-H..A Calc 178(2), Rep 178.00 ...... Missing su N2 -H2A -CL1 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 0 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: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLUTON (Spek, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).
C12H14FN2O+·Cl− | F(000) = 536 |
Mr = 256.70 | Dx = 1.425 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 998 reflections |
a = 13.020 (6) Å | θ = 7–55° |
b = 6.608 (3) Å | µ = 0.32 mm−1 |
c = 15.119 (7) Å | T = 293 K |
β = 113.109 (7)° | Needle, colorless |
V = 1196.4 (9) Å3 | 0.5 × 0.2 × 0.08 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 2854 independent reflections |
Radiation source: fine-focus sealed tube | 2554 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
ω scans | θmax = 28.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→17 |
Tmin = 0.971, Tmax = 0.984 | k = −8→8 |
13392 measured reflections | l = −19→19 |
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: difference Fourier map |
wR(F2) = 0.116 | All H-atom parameters refined |
S = 1.10 | w = 1/[σ2(Fo2) + (0.068P)2 + 0.2204P] where P = (Fo2 + 2Fc2)/3 |
2854 reflections | (Δ/σ)max < 0.001 |
210 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
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. Weighted least-squares planes through the starred atoms (Nardelli, Musatti, Domiano & Andreetti Ric·Sci.(1965),15(II—A),807). Equation of the plane: m1*X+m2*Y+m3*Z=d Plane 1 m1 = 0.61410(0.00027) m2 = -0.25002(0.00040) m3 = -0.74858(0.00020) D = -2.21287(0.00292) Atom d s d/s (d/s)**2 N1 * 0.0047 0.0013 3.493 12.198 O1 * -0.0104 0.0012 - 8.611 74.149 C1 * -0.0145 0.0015 - 9.441 89.129 C2 * -0.0320 0.0015 - 21.630 467.864 C3 * -0.0120 0.0015 - 8.135 66.178 C4 * 0.0445 0.0015 30.006 900.372 C9 * -0.0363 0.0016 - 22.465 504.691 C10 * -0.0034 0.0018 - 1.905 3.629 C11 * 0.0487 0.0017 28.368 804.716 C12 * 0.0281 0.0018 15.936 253.954 C5 - 1.2323 0.0017 - 704.210 495911.938 C8 0.2742 0.0017 160.592 25789.936 ============ Sum((d/s)**2) for starred atoms 3176.879 Chi-squared at 95% for 7 degrees of freedom: 14.10 The group of atoms deviates significantly from planarity Ring puckering coordinates following Cremer D. & Pople J·A., JACS (1975).97,1354 Ring 1 Atom Internal Cartesian coordinates X Y Z N2 0.0000(0.0000) 1.4193(0.0015) -0.2194(0.0011) C6 1.2428(0.0019) 0.7305(0.0022) 0.2248(0.0012) C5 1.2541(0.0016) -0.7118(0.0022) -0.2390(0.0014) C4 - 0.0055(0.0021) -1.4496(0.0015) 0.2478(0.0013) C8 - 1.2460(0.0018) -0.7141(0.0022) -0.2425(0.0012) C7 - 1.2453(0.0021) 0.7257(0.0021) 0.2283(0.0012) q2 = 0.0248(0.0015) q3 = -0.5723(0.0018) phi2 = 8.23 (4.02) Total puckering amplitude: QT = 0.5728(0.0018) Spherical polar angles: Theta2 = 177.51 (0.15) Asymmetry parameters Following Nardelli M., Acta Cryst.(1983). C39, 1141 N2 C6 C5 C4 C8 C7 DS(N2) =0.0027(0.0009) DS(N2 –C7) =0.3207(0.0007) D2(N2) =0.2535(0.0006) D2(N2 –C7) =0.0080(0.0007) DS(C6) =0.0114(0.0009) DS(C6 –N2) =0.3208(0.0007) D2(C6) =0.2535(0.0006) D2(C6 –N2) =0.0043(0.0008) DS(C5) =0.0141(0.0009) DS(C5 –C6) =0.3206(0.0007) D2(C5) =0.2536(0.0006) D2(C5 –C6) =0.0121(0.0007) |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.90572 (3) | 0.80225 (6) | 0.81904 (3) | 0.04445 (14) | |
F1 | 0.19378 (8) | 0.68630 (18) | 0.17792 (10) | 0.0722 (4) | |
O1 | 0.51737 (9) | 0.37273 (16) | 0.40873 (8) | 0.0458 (3) | |
N1 | 0.62713 (10) | 0.45145 (18) | 0.46085 (9) | 0.0420 (3) | |
N2 | 0.91903 (11) | 0.9547 (2) | 0.62951 (9) | 0.0431 (3) | |
H2A | 0.9155 (18) | 0.904 (4) | 0.6879 (17) | 0.071 (6)* | |
H2B | 0.983 (2) | 1.043 (4) | 0.6486 (17) | 0.074 (7)* | |
C1 | 0.45417 (12) | 0.5255 (2) | 0.35510 (10) | 0.0365 (3) | |
C2 | 0.51628 (11) | 0.7022 (2) | 0.37091 (10) | 0.0327 (3) | |
C3 | 0.62493 (11) | 0.6419 (2) | 0.43840 (10) | 0.0334 (3) | |
C4 | 0.72809 (11) | 0.7697 (2) | 0.47804 (10) | 0.0339 (3) | |
H4 | 0.7355 (15) | 0.829 (2) | 0.4222 (12) | 0.039 (4)* | |
C5 | 0.71414 (13) | 0.9426 (2) | 0.54063 (12) | 0.0422 (3) | |
H5A | 0.7055 (16) | 0.886 (3) | 0.5957 (14) | 0.051 (5)* | |
H5B | 0.6486 (17) | 1.022 (3) | 0.5055 (15) | 0.055 (5)* | |
C6 | 0.81693 (14) | 1.0762 (2) | 0.57675 (13) | 0.0472 (4) | |
H6A | 0.8106 (18) | 1.177 (3) | 0.6212 (16) | 0.065 (6)* | |
H6B | 0.8283 (18) | 1.134 (3) | 0.5254 (16) | 0.062 (6)* | |
C7 | 0.93497 (13) | 0.7844 (3) | 0.57111 (13) | 0.0470 (4) | |
H7A | 1.0038 (19) | 0.710 (3) | 0.6136 (16) | 0.067 (6)* | |
H7B | 0.9503 (16) | 0.845 (3) | 0.5148 (14) | 0.052 (5)* | |
C8 | 0.83286 (12) | 0.6491 (2) | 0.53548 (12) | 0.0406 (3) | |
H8A | 0.8232 (14) | 0.580 (3) | 0.5899 (13) | 0.049 (5)* | |
H8B | 0.8450 (16) | 0.551 (3) | 0.4961 (15) | 0.057 (5)* | |
C9 | 0.46733 (12) | 0.8796 (2) | 0.32252 (11) | 0.0379 (3) | |
H9 | 0.5063 (14) | 1.001 (3) | 0.3321 (12) | 0.042 (4)* | |
C10 | 0.35717 (13) | 0.8715 (3) | 0.25845 (12) | 0.0447 (4) | |
H10 | 0.3207 (16) | 0.987 (3) | 0.2229 (14) | 0.056 (5)* | |
C11 | 0.30041 (12) | 0.6883 (3) | 0.24399 (12) | 0.0457 (4) | |
C12 | 0.34323 (13) | 0.5108 (3) | 0.29069 (12) | 0.0439 (3) | |
H12 | 0.3020 (16) | 0.400 (3) | 0.2766 (13) | 0.051 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0414 (2) | 0.0431 (2) | 0.0450 (2) | 0.00619 (14) | 0.01274 (16) | 0.00682 (14) |
F1 | 0.0307 (5) | 0.0748 (8) | 0.0844 (8) | 0.0021 (5) | −0.0064 (5) | 0.0028 (6) |
O1 | 0.0383 (6) | 0.0342 (5) | 0.0538 (6) | −0.0058 (4) | 0.0063 (5) | 0.0036 (5) |
N1 | 0.0338 (6) | 0.0351 (6) | 0.0473 (7) | −0.0031 (5) | 0.0054 (5) | 0.0024 (5) |
N2 | 0.0392 (7) | 0.0433 (7) | 0.0377 (6) | −0.0123 (5) | 0.0053 (5) | 0.0000 (5) |
C1 | 0.0331 (7) | 0.0354 (7) | 0.0385 (7) | −0.0026 (5) | 0.0113 (6) | 0.0000 (5) |
C2 | 0.0303 (6) | 0.0333 (7) | 0.0331 (6) | −0.0014 (5) | 0.0107 (5) | −0.0014 (5) |
C3 | 0.0311 (6) | 0.0326 (6) | 0.0334 (6) | −0.0012 (5) | 0.0095 (5) | −0.0009 (5) |
C4 | 0.0307 (6) | 0.0333 (6) | 0.0332 (6) | −0.0024 (5) | 0.0076 (5) | 0.0015 (5) |
C5 | 0.0364 (8) | 0.0353 (7) | 0.0491 (8) | −0.0003 (6) | 0.0104 (6) | −0.0050 (6) |
C6 | 0.0494 (9) | 0.0346 (7) | 0.0492 (9) | −0.0067 (7) | 0.0102 (7) | −0.0039 (7) |
C7 | 0.0313 (7) | 0.0483 (9) | 0.0539 (10) | −0.0047 (6) | 0.0086 (7) | −0.0031 (7) |
C8 | 0.0297 (7) | 0.0366 (7) | 0.0486 (8) | −0.0012 (5) | 0.0079 (6) | −0.0030 (6) |
C9 | 0.0352 (7) | 0.0345 (7) | 0.0417 (7) | 0.0006 (6) | 0.0128 (6) | 0.0024 (6) |
C10 | 0.0380 (8) | 0.0443 (8) | 0.0461 (8) | 0.0080 (6) | 0.0105 (6) | 0.0060 (7) |
C11 | 0.0267 (7) | 0.0568 (9) | 0.0462 (8) | 0.0020 (6) | 0.0064 (6) | −0.0031 (7) |
C12 | 0.0319 (7) | 0.0444 (8) | 0.0514 (9) | −0.0081 (6) | 0.0119 (6) | −0.0047 (7) |
F1—C11 | 1.3553 (18) | C5—C6 | 1.515 (2) |
O1—C1 | 1.3529 (18) | C5—H5A | 0.96 (2) |
O1—N1 | 1.4317 (17) | C5—H5B | 0.96 (2) |
N1—C3 | 1.3007 (19) | C6—H6A | 0.97 (2) |
N2—C6 | 1.489 (2) | C6—H6B | 0.93 (2) |
N2—C7 | 1.494 (2) | C7—C8 | 1.515 (2) |
N2—H2A | 0.96 (2) | C7—H7A | 1.00 (2) |
N2—H2B | 0.96 (3) | C7—H7B | 1.03 (2) |
C1—C2 | 1.387 (2) | C8—H8A | 0.991 (19) |
C1—C12 | 1.393 (2) | C8—H8B | 0.93 (2) |
C2—C9 | 1.396 (2) | C9—C10 | 1.381 (2) |
C2—C3 | 1.4382 (19) | C9—H9 | 0.930 (18) |
C3—C4 | 1.4984 (19) | C10—C11 | 1.390 (2) |
C4—C8 | 1.523 (2) | C10—H10 | 0.95 (2) |
C4—C5 | 1.539 (2) | C11—C12 | 1.370 (2) |
C4—H4 | 0.970 (17) | C12—H12 | 0.88 (2) |
C1—O1—N1 | 107.44 (11) | N2—C6—H6A | 107.4 (13) |
C3—N1—O1 | 107.03 (11) | C5—C6—H6A | 110.2 (13) |
C6—N2—C7 | 113.05 (12) | N2—C6—H6B | 105.6 (14) |
C6—N2—H2A | 108.9 (14) | C5—C6—H6B | 110.3 (14) |
C7—N2—H2A | 110.5 (14) | H6A—C6—H6B | 112.4 (19) |
C6—N2—H2B | 108.4 (14) | N2—C7—C8 | 110.39 (14) |
C7—N2—H2B | 109.4 (14) | N2—C7—H7A | 106.7 (13) |
H2A—N2—H2B | 106.4 (19) | C8—C7—H7A | 112.2 (13) |
O1—C1—C2 | 110.41 (12) | N2—C7—H7B | 108.1 (11) |
O1—C1—C12 | 125.93 (13) | C8—C7—H7B | 111.4 (11) |
C2—C1—C12 | 123.64 (14) | H7A—C7—H7B | 107.9 (16) |
C1—C2—C9 | 120.08 (13) | C7—C8—C4 | 111.01 (13) |
C1—C2—C3 | 103.50 (12) | C7—C8—H8A | 110.9 (11) |
C9—C2—C3 | 136.40 (13) | C4—C8—H8A | 109.7 (10) |
N1—C3—C2 | 111.60 (12) | C7—C8—H8B | 107.0 (12) |
N1—C3—C4 | 121.11 (13) | C4—C8—H8B | 109.7 (12) |
C2—C3—C4 | 127.24 (12) | H8A—C8—H8B | 108.5 (17) |
C3—C4—C8 | 113.24 (12) | C10—C9—C2 | 118.04 (14) |
C3—C4—C5 | 111.15 (12) | C10—C9—H9 | 119.7 (11) |
C8—C4—C5 | 109.47 (12) | C2—C9—H9 | 122.3 (11) |
C3—C4—H4 | 105.1 (11) | C9—C10—C11 | 119.04 (14) |
C8—C4—H4 | 109.6 (10) | C9—C10—H10 | 121.2 (12) |
C5—C4—H4 | 108.1 (10) | C11—C10—H10 | 119.7 (12) |
C6—C5—C4 | 110.70 (13) | F1—C11—C12 | 117.60 (15) |
C6—C5—H5A | 107.6 (12) | F1—C11—C10 | 116.88 (15) |
C4—C5—H5A | 109.1 (12) | C12—C11—C10 | 125.52 (14) |
C6—C5—H5B | 110.4 (12) | C11—C12—C1 | 113.64 (14) |
C4—C5—H5B | 110.9 (12) | C11—C12—H12 | 119.9 (13) |
H5A—C5—H5B | 108.1 (16) | C1—C12—H12 | 126.4 (13) |
N2—C6—C5 | 110.82 (13) | ||
C1—O1—N1—C3 | 0.97 (16) | C3—C4—C5—C6 | −177.53 (13) |
N1—O1—C1—C2 | −1.29 (16) | C8—C4—C5—C6 | 56.63 (17) |
N1—O1—C1—C12 | 177.14 (15) | C7—N2—C6—C5 | 55.83 (19) |
O1—C1—C2—C9 | 179.87 (13) | C4—C5—C6—N2 | −55.70 (18) |
C12—C1—C2—C9 | 1.4 (2) | C6—N2—C7—C8 | −55.94 (19) |
O1—C1—C2—C3 | 1.08 (16) | N2—C7—C8—C4 | 56.50 (19) |
C12—C1—C2—C3 | −177.39 (14) | C3—C4—C8—C7 | 178.20 (13) |
O1—N1—C3—C2 | −0.30 (16) | C5—C4—C8—C7 | −57.17 (18) |
O1—N1—C3—C4 | −177.88 (12) | C1—C2—C9—C10 | −0.9 (2) |
C1—C2—C3—N1 | −0.46 (16) | C3—C2—C9—C10 | 177.38 (15) |
C9—C2—C3—N1 | −178.94 (16) | C2—C9—C10—C11 | −0.8 (2) |
C1—C2—C3—C4 | 176.95 (13) | C9—C10—C11—F1 | −177.70 (14) |
C9—C2—C3—C4 | −1.5 (3) | C9—C10—C11—C12 | 2.2 (3) |
N1—C3—C4—C8 | 6.3 (2) | F1—C11—C12—C1 | 178.19 (14) |
C2—C3—C4—C8 | −170.84 (13) | C10—C11—C12—C1 | −1.7 (3) |
N1—C3—C4—C5 | −117.37 (15) | O1—C1—C12—C11 | −178.34 (15) |
C2—C3—C4—C5 | 65.45 (18) | C2—C1—C12—C11 | −0.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···Cl1 | 0.96 (3) | 2.15 (3) | 3.106 (2) | 178 |
N2—H2B···Cl1i | 0.96 (3) | 2.17 (2) | 3.113 (2) | 166 |
C7—H7A···F1ii | 1.00 (2) | 2.38 (2) | 3.119 (2) | 130 |
C9—H9···O1iii | 0.93 (2) | 2.69 (2) | 3.475 (2) | 142 |
Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) x+1, −y+3/2, z+1/2; (iii) x, y+1, z. |
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