Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806000353/ci6733sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806000353/ci6733Isup2.hkl |
CCDC reference: 298391
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.020 Å
- Disorder in main residue
- R factor = 0.047
- wR factor = 0.138
- Data-to-parameter ratio = 8.4
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 24.93 Deg.
Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C1' PLAT341_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 20
Alert level C PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2 PLAT301_ALERT_3_C Main Residue Disorder ......................... 21.00 Perc. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 7
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 24.93 From the CIF: _reflns_number_total 1072 Count of symmetry unique reflns 1074 Completeness (_total/calc) 99.81% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software; 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: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
C9H14N+·Br− | F(000) = 440 |
Mr = 216.12 | Dx = 1.370 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
a = 8.3040 (17) Å | θ = 10–13° |
b = 10.783 (2) Å | µ = 3.87 mm−1 |
c = 11.699 (2) Å | T = 293 K |
V = 1047.6 (3) Å3 | Block, colourless |
Z = 4 | 0.40 × 0.30 × 0.20 mm |
Enraf–Nonius CAD-4 diffractometer | 641 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 24.9°, θmin = 2.6° |
ω/2θ scans | h = 0→9 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→12 |
Tmin = 0.276, Tmax = 0.461 | l = 0→13 |
1072 measured reflections | 3 standard reflections every 200 reflections |
1072 independent reflections | intensity decay: none |
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)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.138 | w = 1/[σ2(Fo2) + (0.0758P)2 + 0.5P] where P = (Fo2 + 2Fc2)/3 |
S = 0.95 | (Δ/σ)max = 0.001 |
1072 reflections | Δρmax = 0.36 e Å−3 |
127 parameters | Δρmin = −0.51 e Å−3 |
42 restraints | Absolute structure: Flack (1983); 0 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.02 (6) |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Br1 | 0.97562 (13) | 0.28210 (12) | 0.39186 (10) | 0.0616 (4) | |
N1 | 0.6028 (12) | 0.4970 (10) | 0.2147 (9) | 0.057 (3) | |
C1 | 0.750 (4) | 0.267 (3) | −0.089 (3) | 0.088 (10) | 0.50 |
H1A | 0.6703 | 0.2496 | −0.1463 | 0.132* | 0.50 |
H1B | 0.7754 | 0.1924 | −0.0483 | 0.132* | 0.50 |
H1C | 0.8449 | 0.2994 | −0.1245 | 0.132* | 0.50 |
C2 | 0.683 (3) | 0.363 (2) | −0.0055 (17) | 0.070 (7) | 0.50 |
H2A | 0.5828 | 0.3325 | 0.0269 | 0.084* | 0.50 |
H2B | 0.6601 | 0.4393 | −0.0459 | 0.084* | 0.50 |
C3 | 0.804 (3) | 0.388 (2) | 0.090 (2) | 0.072 (9) | 0.50 |
H3A | 0.8096 | 0.3143 | 0.1379 | 0.086* | 0.50 |
H3B | 0.9088 | 0.3994 | 0.0559 | 0.086* | 0.50 |
C1' | 0.743 (6) | 0.229 (4) | −0.056 (3) | 0.118 (16) | 0.50 |
H1'A | 0.7228 | 0.1426 | −0.0439 | 0.178* | 0.50 |
H1'B | 0.8441 | 0.2398 | −0.0942 | 0.178* | 0.50 |
H1'C | 0.6582 | 0.2640 | −0.1017 | 0.178* | 0.50 |
C2' | 0.748 (4) | 0.296 (2) | 0.060 (2) | 0.087 (9) | 0.50 |
H2'A | 0.8271 | 0.2549 | 0.1076 | 0.104* | 0.50 |
H2'B | 0.6439 | 0.2867 | 0.0962 | 0.104* | 0.50 |
C3' | 0.789 (4) | 0.434 (2) | 0.0534 (18) | 0.084 (11) | 0.50 |
H3'A | 0.8993 | 0.4430 | 0.0272 | 0.101* | 0.50 |
H3'B | 0.7193 | 0.4733 | −0.0022 | 0.101* | 0.50 |
C4 | 0.7704 (18) | 0.4987 (15) | 0.1678 (13) | 0.095 (5) | |
H4A | 0.8466 | 0.4982 | 0.2307 | 0.114* | 0.50 |
H4B | 0.7865 | 0.5747 | 0.1249 | 0.114* | 0.50 |
H4C | 0.8437 | 0.4615 | 0.2212 | 0.114* | 0.50 |
H4D | 0.8018 | 0.5836 | 0.1568 | 0.114* | 0.50 |
C5 | 0.5695 (16) | 0.4232 (12) | 0.3036 (10) | 0.058 (3) | |
H5 | 0.6517 | 0.3759 | 0.3355 | 0.069* | |
C6 | 0.4214 (19) | 0.4156 (13) | 0.3480 (11) | 0.073 (4) | |
H6 | 0.3995 | 0.3653 | 0.4107 | 0.087* | |
C7 | 0.3030 (18) | 0.4854 (15) | 0.2971 (13) | 0.082 (4) | |
H7 | 0.1979 | 0.4807 | 0.3241 | 0.099* | |
C8 | 0.3378 (19) | 0.5613 (15) | 0.2078 (14) | 0.085 (5) | |
H8 | 0.2583 | 0.6115 | 0.1762 | 0.103* | |
C9 | 0.490 (2) | 0.5631 (11) | 0.1651 (10) | 0.074 (4) | |
H9 | 0.5136 | 0.6109 | 0.1012 | 0.089* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0563 (6) | 0.0669 (7) | 0.0617 (6) | −0.0017 (6) | −0.0001 (6) | −0.0046 (7) |
N1 | 0.049 (6) | 0.057 (7) | 0.067 (7) | −0.015 (6) | 0.014 (6) | −0.011 (6) |
C1 | 0.090 (13) | 0.088 (13) | 0.086 (13) | 0.009 (9) | 0.003 (9) | 0.002 (10) |
C2 | 0.076 (11) | 0.064 (11) | 0.069 (10) | −0.005 (9) | 0.006 (9) | 0.000 (9) |
C3 | 0.063 (11) | 0.084 (12) | 0.068 (11) | −0.002 (9) | 0.005 (9) | 0.007 (9) |
C1' | 0.116 (18) | 0.123 (18) | 0.116 (18) | 0.004 (10) | 0.016 (10) | 0.000 (10) |
C2' | 0.087 (11) | 0.091 (12) | 0.083 (12) | 0.003 (9) | 0.007 (9) | −0.005 (9) |
C3' | 0.080 (14) | 0.083 (14) | 0.089 (14) | 0.000 (9) | 0.007 (9) | 0.012 (10) |
C4 | 0.074 (11) | 0.097 (11) | 0.115 (13) | −0.040 (9) | 0.021 (10) | −0.022 (11) |
C5 | 0.073 (9) | 0.055 (8) | 0.045 (7) | 0.000 (7) | −0.009 (7) | 0.012 (6) |
C6 | 0.099 (11) | 0.071 (10) | 0.048 (8) | −0.024 (8) | 0.019 (7) | 0.017 (7) |
C7 | 0.065 (11) | 0.096 (12) | 0.086 (10) | −0.018 (9) | 0.007 (9) | −0.027 (10) |
C8 | 0.075 (11) | 0.088 (12) | 0.093 (11) | 0.018 (9) | −0.027 (9) | −0.015 (10) |
C9 | 0.110 (13) | 0.051 (8) | 0.060 (7) | 0.023 (10) | −0.007 (9) | 0.015 (6) |
N1—C9 | 1.314 (15) | C2'—H2'A | 0.97 |
N1—C5 | 1.339 (15) | C2'—H2'B | 0.97 |
N1—C4 | 1.496 (16) | C3'—C4 | 1.519 (10) |
C1—C2 | 1.523 (10) | C3'—H3'A | 0.97 |
C1—H1A | 0.96 | C3'—H3'B | 0.97 |
C1—H1B | 0.96 | C4—H4A | 0.97 |
C1—H1C | 0.96 | C4—H4B | 0.97 |
C2—C3 | 1.528 (10) | C4—H4C | 0.96 |
C2—H2A | 0.97 | C4—H4D | 0.96 |
C2—H2B | 0.97 | C5—C6 | 1.337 (18) |
C3—C4 | 1.525 (10) | C5—H5 | 0.93 |
C3—H3A | 0.97 | C6—C7 | 1.374 (19) |
C3—H3B | 0.97 | C6—H6 | 0.93 |
C1'—C2' | 1.528 (10) | C7—C8 | 1.36 (2) |
C1'—H1'A | 0.96 | C7—H7 | 0.93 |
C1'—H1'B | 0.96 | C8—C9 | 1.357 (17) |
C1'—H1'C | 0.96 | C8—H8 | 0.93 |
C2'—C3' | 1.528 (10) | C9—H9 | 0.93 |
C9—N1—C5 | 121.2 (10) | C2'—C3'—H3'A | 109.1 |
C9—N1—C4 | 119.8 (13) | C4—C3'—H3'B | 109.1 |
C5—N1—C4 | 119.0 (13) | C2'—C3'—H3'B | 109.1 |
C2—C1—H1A | 109.5 | H3'A—C3'—H3'B | 107.8 |
C2—C1—H1B | 109.5 | N1—C4—C3' | 114.3 (17) |
H1A—C1—H1B | 109.5 | N1—C4—C3 | 112.1 (14) |
C2—C1—H1C | 109.5 | N1—C4—H4A | 109.2 |
H1A—C1—H1C | 109.5 | C3'—C4—H4A | 126.8 |
H1B—C1—H1C | 109.5 | C3—C4—H4A | 109.2 |
C1—C2—C3 | 110.6 (19) | N1—C4—H4B | 109.2 |
C1—C2—H2A | 109.5 | C3'—C4—H4B | 85.4 |
C3—C2—H2A | 109.5 | C3—C4—H4B | 109.2 |
C1—C2—H2B | 109.5 | H4A—C4—H4B | 107.9 |
C3—C2—H2B | 109.5 | N1—C4—H4C | 110.3 |
H2A—C2—H2B | 108.1 | C3'—C4—H4C | 108.4 |
C4—C3—C2 | 117.2 (17) | C3—C4—H4C | 86.8 |
C4—C3—H3A | 108.0 | N1—C4—H4D | 108.3 |
C2—C3—H3A | 108.0 | C3'—C4—H4D | 107.1 |
C4—C3—H3B | 108.0 | C3—C4—H4D | 128.2 |
C2—C3—H3B | 108.0 | H4C—C4—H4D | 108.3 |
H3A—C3—H3B | 107.2 | C6—C5—N1 | 121.9 (12) |
C2'—C1'—H1'A | 109.5 | C6—C5—H5 | 119.1 |
C2'—C1'—H1'B | 109.5 | N1—C5—H5 | 119.1 |
H1'A—C1'—H1'B | 109.5 | C5—C6—C7 | 117.1 (12) |
C2'—C1'—H1'C | 109.5 | C5—C6—H6 | 121.4 |
H1'A—C1'—H1'C | 109.5 | C7—C6—H6 | 121.4 |
H1'B—C1'—H1'C | 109.5 | C8—C7—C6 | 120.8 (14) |
C1'—C2'—C3' | 115 (2) | C8—C7—H7 | 119.6 |
C1'—C2'—H2'A | 108.5 | C6—C7—H7 | 119.6 |
C3'—C2'—H2'A | 108.5 | C9—C8—C7 | 119.3 (14) |
C1'—C2'—H2'B | 108.5 | C9—C8—H8 | 120.3 |
C3'—C2'—H2'B | 108.5 | C7—C8—H8 | 120.3 |
H2'A—C2'—H2'B | 107.5 | N1—C9—C8 | 119.6 (12) |
C4—C3'—C2' | 112.6 (19) | N1—C9—H9 | 120.2 |
C4—C3'—H3'A | 109.1 | C8—C9—H9 | 120.2 |
C1—C2—C3—C4 | 168 (2) | C2—C3—C4—C3' | −49 (4) |
C1'—C2'—C3'—C4 | 172 (3) | C9—N1—C5—C6 | −2 (2) |
C9—N1—C4—C3' | −70 (2) | C4—N1—C5—C6 | −178.7 (12) |
C5—N1—C4—C3' | 107.0 (18) | N1—C5—C6—C7 | 1 (2) |
C9—N1—C4—C3 | −97.5 (19) | C5—C6—C7—C8 | −2 (2) |
C5—N1—C4—C3 | 79.5 (19) | C6—C7—C8—C9 | 3 (2) |
C2'—C3'—C4—N1 | −62 (3) | C5—N1—C9—C8 | 3.0 (19) |
C2'—C3'—C4—C3 | 29 (3) | C4—N1—C9—C8 | 179.9 (13) |
C2—C3—C4—N1 | 51 (3) | C7—C8—C9—N1 | −4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4D···Br1i | 0.96 | 2.88 | 3.778 (16) | 155 |
C6—H6···Br1ii | 0.93 | 2.87 | 3.743 (13) | 156 |
C8—H8···Br1iii | 0.93 | 2.79 | 3.715 (16) | 172 |
C9—H9···Br1iv | 0.93 | 2.71 | 3.618 (12) | 166 |
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) x−1/2, −y+1/2, −z+1; (iii) −x+1, y+1/2, −z+1/2; (iv) −x+3/2, −y+1, z−1/2. |
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