Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807009427/sq3066sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807009427/sq3066Isup2.hkl |
CCDC reference: 643116
Key indicators
- Single-crystal X-ray study
- T = 103 K
- Mean (C-C) = 0.001 Å
- R factor = 0.027
- wR factor = 0.072
- Data-to-parameter ratio = 93.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) . 100 Ang. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 52.30 From the CIF: _reflns_number_total 16560 Count of symmetry unique reflns 9541 Completeness (_total/calc) 173.57% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 7019 Fraction of Friedel pairs measured 0.736 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: HKL-2000 (Otwinowski & Minor, 1997); cell refinement: HKL-2000; data reduction: HKL-2000; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990) and HKL-3000SM (Minor et al., 2006); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) and HKL-3000SM; molecular graphics: HKL-3000SM, ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: HKL-3000SM.
C13H16ClN2S+·I− | F(000) = 776 |
Mr = 394.69 | Dx = 1.736 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71074 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 107797 reflections |
a = 7.761 (1) Å | θ = 2.3–52.3° |
b = 9.659 (1) Å | µ = 2.42 mm−1 |
c = 20.145 (1) Å | T = 103 K |
V = 1510.1 (3) Å3 | Block, yellow |
Z = 4 | 0.53 × 0.26 × 0.26 mm |
Rigaku R-AXIS RAPID diffractometer | 16521 independent reflections |
Radiation source: fine-focus sealed tube | 14434 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
Detector resolution: 10 pixels mm-1 | θmax = 52.3°, θmin = 2.3° |
ω scans with χ offset | h = −16→16 |
Absorption correction: multi-scan (Otwinowski et al., 2003) | k = −21→21 |
Tmin = 0.47, Tmax = 0.53 | l = −44→44 |
107797 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.027 | w = 1/[σ2(Fo2) + (0.0474P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.072 | (Δ/σ)max = 0.001 |
S = 1.01 | Δρmax = 1.24 e Å−3 |
16517 reflections | Δρmin = −0.98 e Å−3 |
176 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0111 (5) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 7019 Friedel pairs? |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.001 (6) |
Experimental. NMR spectra were recorded using a Varian-300 spectrometer for 1H (300 MHz) and 13C (75 MHz). Chemical shifts (δ) are given in p.p.m. downfield from tetramethylsilane as internal standard, and coupling constants (J values) are in hertz. Mass spectra data were collected on a Finnigan MAT LC—Q mass spectrometer system using electrospray ionization (ESI). Elemental analyses were performed by Atlantic Microlabs. Melting points were obtained using an electrothermal digital melting point apparatus and are uncorrected. All purifications by flash chromatography were performed using Geduran silica gel 60, 35–75µm (VWR). For (1): 1H NMR (CDCl3) δ 2.28 (s, 3H), 7.33 (d, J = 8.1 Hz), 7.49 (d, J = 8.1 Hz), 7.57 (s, 1H), 9.81 (s, 1H). For (2): 1H NMR (CDCl3) δ 0.88 (t, J = 7.2, 6.9 Hz, 3H), 1.28 - 1.40 (m, 2H), 1.65 - 1.94 (m, 3H), 2.37 (s, 3H), 4.58 - 4.63 (m, 1H), 7.08 - 7.15 (m, 1H), 7.16 - 7.33 (m, 2H). For (3): 1H NMR (CDCl3) δ 0.88 (t, J = 7.2, 7.2 Hz, 3H), 1.26 - 1.39 (m, 2H), 1.57 - 1.67 (m, 2H), 2.32 (s, 3H), 2.83 (t, J = 6.9, 7.8 Hz, 2H), 7.29 (d, J = 8.1 Hz, 1H), 7.61 (d, J = 8.1 Hz, 1H), 7.73 (s, 1H); 13C NMR (CDCl3) δ 13.94, 20.03, 22.45, 26.37, 38.23, 126.77, 129.16, 130.40, 135.44, 136.36, 139.28, 199.27; APCI m/z 211 [M+H]+. For (I): 1H NMR (DMSO-d6) δ 0.86 (t, J = 7.5, 7.2 Hz, 3H), 1.48 - 1.60 (m, 2H), 2.39 (s, 3H), 2.62 (t, J = 7.5, 7.5 Hz, 2H), 7.34 (dd, J = 2.1, 2.1 Hz, 1H), 7.49 (d, J = 1.8 Hz, 1H), 7.57 (d, J = 8.4 Hz, 1H), 8.80 (br s, 2H); APCI m/z 395 [M+H]+; Anal. Calcd. for C13H16ClIN2S: C, 39.56; H, 4.09; N, 7.10. Found: C, 39.64; H, 4.14; N, 7.06. |
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) | |
I1 | 0.435396 (9) | 0.147814 (6) | 0.129970 (3) | 0.02266 (2) | |
S1 | 0.66083 (3) | 0.59544 (2) | 0.176000 (11) | 0.02010 (4) | |
Cl1 | 0.68767 (4) | 0.90064 (3) | −0.220879 (12) | 0.02924 (5) | |
C7 | 0.61921 (12) | 0.66781 (9) | −0.05937 (4) | 0.01859 (11) | |
H7 | 0.5837 | 0.5784 | −0.0490 | 0.022* | |
N1 | 0.60319 (11) | 0.81119 (8) | 0.10852 (3) | 0.01909 (11) | |
C5 | 0.69493 (12) | 0.58856 (9) | 0.08993 (4) | 0.01833 (11) | |
C6 | 0.66899 (11) | 0.75651 (9) | −0.00818 (4) | 0.01716 (10) | |
C4 | 0.65752 (11) | 0.71285 (8) | 0.06174 (4) | 0.01732 (11) | |
C9 | 0.68185 (12) | 0.84269 (10) | −0.13947 (4) | 0.02040 (12) | |
C12 | 0.75770 (13) | 0.45677 (9) | 0.05918 (5) | 0.02171 (13) | |
H12A | 0.8290 | 0.4793 | 0.0211 | 0.026* | |
H12B | 0.6592 | 0.4047 | 0.0432 | 0.026* | |
C2 | 0.59492 (12) | 0.76502 (9) | 0.17101 (4) | 0.01943 (12) | |
N2 | 0.54162 (15) | 0.84122 (9) | 0.22153 (4) | 0.02564 (15) | |
C8 | 0.62112 (12) | 0.70931 (9) | −0.12589 (4) | 0.01944 (11) | |
C13 | 0.86102 (13) | 0.36576 (10) | 0.10630 (5) | 0.02203 (13) | |
H13A | 0.7871 | 0.3348 | 0.1422 | 0.026* | |
H13B | 0.9540 | 0.4196 | 0.1255 | 0.026* | |
C15 | 0.55685 (17) | 0.61508 (12) | −0.17990 (5) | 0.02696 (17) | |
H15A | 0.5209 | 0.5287 | −0.1609 | 0.040* | 0.50 |
H15B | 0.6476 | 0.5987 | −0.2113 | 0.040* | 0.50 |
H15C | 0.4610 | 0.6577 | −0.2020 | 0.040* | 0.50 |
H15D | 0.5655 | 0.6614 | −0.2219 | 0.040* | 0.50 |
H15E | 0.4387 | 0.5914 | −0.1715 | 0.040* | 0.50 |
H15F | 0.6253 | 0.5323 | −0.1808 | 0.040* | 0.50 |
C11 | 0.72521 (12) | 0.89064 (9) | −0.02353 (4) | 0.01973 (12) | |
H11 | 0.7564 | 0.9511 | 0.0103 | 0.024* | |
C14 | 0.9360 (2) | 0.24007 (13) | 0.07063 (7) | 0.0350 (2) | |
H14A | 1.0002 | 0.1849 | 0.1016 | 0.052* | 0.50 |
H14B | 1.0108 | 0.2705 | 0.0356 | 0.052* | 0.50 |
H14C | 0.8440 | 0.1857 | 0.0522 | 0.052* | 0.50 |
H14D | 0.9032 | 0.2425 | 0.0247 | 0.052* | 0.50 |
H14E | 0.8925 | 0.1569 | 0.0907 | 0.052* | 0.50 |
H14F | 1.0593 | 0.2417 | 0.0741 | 0.052* | 0.50 |
C10 | 0.73433 (13) | 0.93341 (10) | −0.08942 (5) | 0.02122 (13) | |
H10 | 0.7749 | 1.0213 | −0.1000 | 0.025* | |
H1 | 0.560 (2) | 0.888 (2) | 0.0987 (9) | 0.022 (4)* | |
H2 | 0.509 (3) | 0.917 (2) | 0.2157 (9) | 0.025 (4)* | |
H3 | 0.563 (2) | 0.815 (3) | 0.2619 (10) | 0.034 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.02939 (3) | 0.01897 (2) | 0.01962 (2) | −0.00002 (2) | −0.00221 (2) | −0.00087 (2) |
S1 | 0.02722 (9) | 0.01763 (7) | 0.01543 (6) | 0.00181 (7) | 0.00103 (6) | 0.00167 (5) |
Cl1 | 0.03470 (12) | 0.03387 (12) | 0.01915 (7) | 0.00243 (10) | 0.00104 (8) | 0.00982 (8) |
C7 | 0.0230 (3) | 0.0174 (3) | 0.0154 (2) | −0.0003 (2) | 0.0000 (2) | 0.00054 (18) |
N1 | 0.0260 (3) | 0.0161 (2) | 0.0152 (2) | 0.0017 (2) | 0.0016 (2) | 0.00017 (17) |
C5 | 0.0232 (3) | 0.0159 (2) | 0.0159 (2) | 0.0005 (2) | 0.0009 (2) | 0.00060 (18) |
C6 | 0.0198 (3) | 0.0164 (2) | 0.0153 (2) | 0.0002 (2) | 0.0003 (2) | 0.00057 (18) |
C4 | 0.0215 (3) | 0.0158 (2) | 0.0146 (2) | 0.0004 (2) | 0.0008 (2) | −0.00011 (18) |
C9 | 0.0218 (3) | 0.0222 (3) | 0.0173 (2) | 0.0033 (3) | 0.0011 (2) | 0.0044 (2) |
C12 | 0.0279 (4) | 0.0175 (3) | 0.0198 (3) | 0.0034 (3) | −0.0001 (3) | −0.0010 (2) |
C2 | 0.0261 (4) | 0.0176 (3) | 0.0146 (2) | 0.0004 (2) | 0.0006 (2) | 0.00009 (19) |
N2 | 0.0404 (4) | 0.0202 (3) | 0.0164 (2) | 0.0038 (3) | 0.0039 (2) | −0.0012 (2) |
C8 | 0.0229 (3) | 0.0203 (3) | 0.0151 (2) | 0.0027 (2) | −0.0002 (2) | −0.0001 (2) |
C13 | 0.0236 (3) | 0.0178 (3) | 0.0248 (3) | 0.0013 (2) | −0.0005 (3) | 0.0013 (2) |
C15 | 0.0350 (5) | 0.0273 (4) | 0.0186 (3) | 0.0033 (4) | −0.0041 (3) | −0.0035 (3) |
C11 | 0.0226 (3) | 0.0173 (3) | 0.0193 (3) | −0.0008 (2) | −0.0001 (2) | 0.0012 (2) |
C14 | 0.0429 (6) | 0.0236 (4) | 0.0385 (6) | 0.0130 (5) | −0.0009 (5) | −0.0018 (4) |
C10 | 0.0236 (3) | 0.0191 (3) | 0.0209 (3) | −0.0006 (3) | 0.0008 (2) | 0.0047 (2) |
S1—C2 | 1.719 (1) | N2—H3 | 0.87 (2) |
S1—C5 | 1.755 (1) | C8—C15 | 1.5037 (13) |
Cl1—C9 | 1.733 (1) | C13—C14 | 1.5260 (15) |
C7—C6 | 1.395 (1) | C13—H13A | 0.9700 |
C7—C8 | 1.399 (1) | C13—H13B | 0.9700 |
C7—H7 | 0.9300 | C15—H15A | 0.9600 |
N1—C2 | 1.337 (1) | C15—H15B | 0.9600 |
N1—C4 | 1.403 (1) | C15—H15C | 0.9600 |
N1—H1 | 0.835 (19) | C15—H15D | 0.9600 |
C5—C4 | 1.359 (1) | C15—H15E | 0.9600 |
C5—C12 | 1.4971 (12) | C15—H15F | 0.9600 |
C6—C11 | 1.4016 (12) | C11—C10 | 1.3919 (12) |
C6—C4 | 1.473 (1) | C11—H11 | 0.9300 |
C9—C10 | 1.3965 (14) | C14—H14A | 0.9600 |
C9—C8 | 1.3989 (13) | C14—H14B | 0.9600 |
C12—C13 | 1.5222 (13) | C14—H14C | 0.9600 |
C12—H12A | 0.9700 | C14—H14D | 0.9600 |
C12—H12B | 0.9700 | C14—H14E | 0.9600 |
C2—N2 | 1.322 (1) | C14—H14F | 0.9600 |
N2—H2 | 0.78 (2) | C10—H10 | 0.9300 |
C2—S1—C5 | 91.33 (4) | H15A—C15—H15C | 109.5 |
C6—C7—C8 | 121.95 (8) | H15B—C15—H15C | 109.5 |
C6—C7—H7 | 119.0 | C8—C15—H15D | 109.5 |
C8—C7—H7 | 119.0 | H15A—C15—H15D | 141.1 |
C2—N1—C4 | 114.90 (7) | H15B—C15—H15D | 56.3 |
C2—N1—H1 | 119.9 (12) | H15C—C15—H15D | 56.3 |
C4—N1—H1 | 124.1 (12) | C8—C15—H15E | 109.5 |
C4—C5—C12 | 130.36 (7) | H15A—C15—H15E | 56.3 |
C4—C5—S1 | 110.30 (6) | H15B—C15—H15E | 141.1 |
C12—C5—S1 | 119.34 (6) | H15C—C15—H15E | 56.3 |
C7—C6—C11 | 119.39 (7) | H15D—C15—H15E | 109.5 |
C7—C6—C4 | 120.94 (7) | C8—C15—H15F | 109.5 |
C11—C6—C4 | 119.63 (7) | H15A—C15—H15F | 56.3 |
C5—C4—N1 | 112.43 (7) | H15B—C15—H15F | 56.3 |
C5—C4—C6 | 129.74 (7) | H15C—C15—H15F | 141.1 |
N1—C4—C6 | 117.82 (7) | H15D—C15—H15F | 109.5 |
C10—C9—C8 | 122.34 (7) | H15E—C15—H15F | 109.5 |
C10—C9—Cl1 | 118.22 (7) | C10—C11—C6 | 120.04 (8) |
C8—C9—Cl1 | 119.42 (7) | C10—C11—H11 | 120.0 |
C5—C12—C13 | 113.85 (8) | C6—C11—H11 | 120.0 |
C5—C12—H12A | 108.8 | C13—C14—H14A | 109.5 |
C13—C12—H12A | 108.8 | C13—C14—H14B | 109.5 |
C5—C12—H12B | 108.8 | H14A—C14—H14B | 109.5 |
C13—C12—H12B | 108.8 | C13—C14—H14C | 109.5 |
H12A—C12—H12B | 107.7 | H14A—C14—H14C | 109.5 |
N2—C2—N1 | 123.64 (8) | H14B—C14—H14C | 109.5 |
N2—C2—S1 | 125.34 (7) | C13—C14—H14D | 109.5 |
N1—C2—S1 | 111.02 (6) | H14A—C14—H14D | 141.1 |
C2—N2—H2 | 120.3 (14) | H14B—C14—H14D | 56.3 |
C2—N2—H3 | 119.9 (16) | H14C—C14—H14D | 56.3 |
H2—N2—H3 | 118 (2) | C13—C14—H14E | 109.5 |
C9—C8—C7 | 117.06 (8) | H14A—C14—H14E | 56.3 |
C9—C8—C15 | 121.85 (8) | H14B—C14—H14E | 141.1 |
C7—C8—C15 | 121.08 (9) | H14C—C14—H14E | 56.3 |
C12—C13—C14 | 111.50 (9) | H14D—C14—H14E | 109.5 |
C12—C13—H13A | 109.3 | C13—C14—H14F | 109.5 |
C14—C13—H13A | 109.3 | H14A—C14—H14F | 56.3 |
C12—C13—H13B | 109.3 | H14B—C14—H14F | 56.3 |
C14—C13—H13B | 109.3 | H14C—C14—H14F | 141.1 |
H13A—C13—H13B | 108.0 | H14D—C14—H14F | 109.5 |
C8—C15—H15A | 109.5 | H14E—C14—H14F | 109.5 |
C8—C15—H15B | 109.5 | C11—C10—C9 | 119.17 (8) |
H15A—C15—H15B | 109.5 | C11—C10—H10 | 120.4 |
C8—C15—H15C | 109.5 | C9—C10—H10 | 120.4 |
C2—S1—C5—C4 | 0.65 (8) | C4—N1—C2—N2 | −177.89 (10) |
C2—S1—C5—C12 | −179.66 (8) | C4—N1—C2—S1 | 1.71 (11) |
C8—C7—C6—C11 | −0.98 (14) | C5—S1—C2—N2 | 178.26 (10) |
C8—C7—C6—C4 | 176.87 (8) | C5—S1—C2—N1 | −1.33 (8) |
C12—C5—C4—N1 | −179.48 (10) | C10—C9—C8—C7 | −1.75 (13) |
S1—C5—C4—N1 | 0.16 (10) | Cl1—C9—C8—C7 | 179.99 (7) |
C12—C5—C4—C6 | −0.64 (17) | C10—C9—C8—C15 | 176.96 (10) |
S1—C5—C4—C6 | 179.01 (8) | Cl1—C9—C8—C15 | −1.30 (12) |
C2—N1—C4—C5 | −1.23 (12) | C6—C7—C8—C9 | 2.45 (14) |
C2—N1—C4—C6 | 179.78 (8) | C6—C7—C8—C15 | −176.26 (9) |
C7—C6—C4—C5 | 40.3 (1) | C5—C12—C13—C14 | −174.56 (10) |
C11—C6—C4—C5 | −141.9 (1) | C7—C6—C11—C10 | −1.29 (14) |
C7—C6—C4—N1 | −141.0 (1) | C4—C6—C11—C10 | −179.17 (8) |
C11—C6—C4—N1 | 36.9 (1) | C6—C11—C10—C9 | 1.97 (14) |
C4—C5—C12—C13 | 153.03 (10) | C8—C9—C10—C11 | −0.43 (14) |
S1—C5—C12—C13 | −26.59 (12) | Cl1—C9—C10—C11 | 177.85 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···I1i | 0.84 (2) | 2.77 (2) | 3.529 (1) | 153 (2) |
N2—H2···I1i | 0.78 (2) | 2.88 (2) | 3.585 (1) | 152 (2) |
N2—H3···I1ii | 0.87 (2) | 2.71 (2) | 3.531 (1) | 158 (2) |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, y+1/2, −z+1/2. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register