Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805018453/lh6447sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805018453/lh6447Isup2.hkl |
CCDC reference: 277723
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.009 Å
- R factor = 0.071
- wR factor = 0.136
- Data-to-parameter ratio = 11.7
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 62.50 Deg.
Author Response: ...' see _exptl_special_details section' |
Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.94 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C15 PLAT331_ALERT_2_B Small Average Phenyl C-C Dist. C15 -C20 1.36 Ang.
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 62.50 From the CIF: _diffrn_reflns_theta_full 62.50 From the CIF: _reflns_number_total 2259 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2391 Completeness (_total/calc) 94.48% THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5753 PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.94 PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6]..... 62.50 Deg. PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.83 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C15 - C16 .. 5.65 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C16 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C17 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C19 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.03 PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
1 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 ALERT type 2 Indicator that the structure model may be wrong or deficient 8 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: Picker Manual (Picker, 1967); cell refinement: Picker Manual; data reduction: DATRDN in The X-ray System (Stewart, 1976); 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: SHELXL97.
C15H14N4S | F(000) = 592 |
Mr = 282.36 | Dx = 1.253 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 13.886 (3) Å | Cell parameters from 32 reflections |
b = 9.898 (2) Å | θ = 19–38° |
c = 10.896 (2) Å | µ = 1.88 mm−1 |
β = 91.46 (2)° | T = 294 K |
V = 1497.1 (5) Å3 | Needle, colorless |
Z = 4 | 0.25 × 0.07 × 0.04 mm |
Picker FACS-1 four-circle diffractometer | 1111 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Ni filtered radiation monochromator | θmax = 62.5°, θmin = 3.2° |
θ/2θ scans | h = 0→15 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→11 |
Tmin = 0.851, Tmax = 0.926 | l = −9→12 |
2259 measured reflections | 3 standard reflections every 100 reflections |
2259 independent reflections | intensity decay: 2.3% |
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)] = 0.071 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.136 | w = 1/[σ2(Fo2) + (0.0477P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.89 | (Δ/σ)max < 0.001 |
2259 reflections | Δρmax = 0.28 e Å−3 |
193 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0014 (3) |
Experimental. Generally no observable reflections above θ = 60° due to poor quality of the crystal and high anisotropic temperature displacement parameters. A few visible reflections from the region θ = 60–65° have been identified on the Weissenberg photographs and duly collected. |
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 | ||
S1 | 0.29751 (10) | 0.10959 (11) | 0.65738 (10) | 0.0663 (5) | |
C2 | 0.3943 (3) | 0.1980 (4) | 0.7163 (4) | 0.0554 (12) | |
N3 | 0.4067 (3) | 0.3187 (4) | 0.6690 (3) | 0.0672 (11) | |
N4 | 0.3356 (3) | 0.3456 (4) | 0.5818 (3) | 0.0659 (11) | |
C5 | 0.2746 (3) | 0.2488 (4) | 0.5631 (4) | 0.0546 (12) | |
N6 | 0.4544 (3) | 0.1436 (4) | 0.8035 (3) | 0.0712 (12) | |
N7 | 0.4229 (4) | 0.0191 (4) | 0.8514 (4) | 0.0691 (13) | |
C8 | 0.5231 (4) | 0.2243 (6) | 0.8746 (5) | 0.0957 (19) | |
H8A | 0.5403 | 0.3028 | 0.8283 | 0.143 (15)* | |
H8B | 0.5798 | 0.1716 | 0.8925 | 0.143 (15)* | |
H8C | 0.4947 | 0.2518 | 0.9500 | 0.143 (15)* | |
C9 | 0.1910 (4) | 0.2645 (4) | 0.4771 (4) | 0.0654 (14) | |
C10 | 0.1511 (4) | 0.1594 (5) | 0.4071 (4) | 0.0695 (14) | |
C11 | 0.0748 (4) | 0.1868 (6) | 0.3240 (5) | 0.100 (2) | |
H11 | 0.0471 | 0.1168 | 0.2783 | 0.123 (7)* | |
C12 | 0.0408 (5) | 0.3162 (7) | 0.3097 (6) | 0.125 (3) | |
H12 | −0.0080 | 0.3339 | 0.2519 | 0.123 (7)* | |
C13 | 0.0781 (5) | 0.4192 (6) | 0.3795 (6) | 0.123 (2) | |
H13 | 0.0527 | 0.5058 | 0.3716 | 0.123 (7)* | |
C14 | 0.1534 (4) | 0.3947 (5) | 0.4618 (5) | 0.0907 (17) | |
H14 | 0.1795 | 0.4656 | 0.5076 | 0.123 (7)* | |
C15 | 0.1850 (4) | 0.0177 (5) | 0.4161 (5) | 0.0659 (14) | |
C16 | 0.2673 (6) | −0.0234 (8) | 0.3623 (6) | 0.126 (3) | |
H16 | 0.3051 | 0.0392 | 0.3218 | 0.123 (7)* | |
C17 | 0.2961 (7) | −0.1603 (10) | 0.3672 (7) | 0.154 (4) | |
H17 | 0.3505 | −0.1886 | 0.3264 | 0.123 (7)* | |
C18 | 0.2457 (7) | −0.2468 (8) | 0.4293 (9) | 0.141 (3) | |
H18 | 0.2657 | −0.3363 | 0.4344 | 0.123 (7)* | |
C19 | 0.1665 (6) | −0.2092 (7) | 0.4852 (9) | 0.147 (4) | |
H19 | 0.1305 | −0.2724 | 0.5274 | 0.123 (7)* | |
C20 | 0.1374 (4) | −0.0762 (6) | 0.4807 (6) | 0.107 (2) | |
H20 | 0.0833 | −0.0503 | 0.5235 | 0.123 (7)* | |
H71 | 0.396 (5) | 0.029 (7) | 0.934 (6) | 0.15 (3)* | |
H72 | 0.477 (5) | −0.033 (7) | 0.854 (5) | 0.13 (3)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0930 (10) | 0.0403 (6) | 0.0643 (8) | −0.0036 (7) | −0.0231 (6) | 0.0088 (6) |
C2 | 0.061 (3) | 0.048 (3) | 0.057 (3) | 0.004 (2) | −0.010 (2) | −0.001 (2) |
N3 | 0.085 (3) | 0.052 (2) | 0.065 (3) | −0.014 (2) | −0.008 (2) | 0.000 (2) |
N4 | 0.093 (3) | 0.048 (2) | 0.055 (2) | −0.010 (2) | −0.017 (2) | 0.0016 (18) |
C5 | 0.076 (3) | 0.042 (3) | 0.045 (3) | 0.002 (2) | −0.006 (3) | 0.003 (2) |
N6 | 0.089 (3) | 0.061 (3) | 0.063 (3) | −0.002 (2) | −0.024 (2) | 0.000 (2) |
N7 | 0.095 (4) | 0.051 (3) | 0.060 (3) | 0.008 (2) | −0.018 (3) | 0.005 (2) |
C8 | 0.114 (5) | 0.101 (4) | 0.071 (4) | −0.023 (4) | −0.023 (4) | 0.006 (3) |
C9 | 0.088 (4) | 0.039 (3) | 0.068 (3) | −0.005 (2) | −0.015 (3) | 0.008 (2) |
C10 | 0.098 (4) | 0.048 (3) | 0.062 (3) | −0.004 (3) | −0.017 (3) | 0.012 (2) |
C11 | 0.120 (5) | 0.067 (4) | 0.109 (5) | −0.009 (4) | −0.058 (4) | 0.008 (3) |
C12 | 0.136 (6) | 0.083 (4) | 0.153 (6) | −0.005 (4) | −0.081 (5) | 0.031 (4) |
C13 | 0.139 (6) | 0.067 (4) | 0.160 (6) | 0.005 (4) | −0.062 (5) | 0.021 (4) |
C14 | 0.111 (5) | 0.049 (3) | 0.111 (4) | 0.007 (3) | −0.030 (4) | 0.006 (3) |
C15 | 0.073 (4) | 0.059 (3) | 0.066 (3) | −0.013 (3) | −0.010 (3) | −0.002 (3) |
C16 | 0.178 (8) | 0.102 (6) | 0.099 (5) | 0.007 (5) | 0.045 (5) | 0.022 (4) |
C17 | 0.205 (10) | 0.128 (7) | 0.131 (7) | 0.063 (7) | 0.073 (6) | −0.013 (6) |
C18 | 0.162 (9) | 0.060 (4) | 0.200 (10) | 0.018 (6) | −0.019 (8) | −0.015 (5) |
C19 | 0.112 (6) | 0.062 (5) | 0.268 (11) | −0.007 (4) | 0.011 (7) | 0.042 (5) |
C20 | 0.082 (5) | 0.065 (4) | 0.174 (6) | −0.002 (3) | 0.008 (4) | 0.018 (4) |
S1—C2 | 1.715 (4) | C11—C12 | 1.373 (8) |
S1—C5 | 1.743 (4) | C11—H11 | 0.9300 |
C2—N3 | 1.314 (5) | C12—C13 | 1.366 (8) |
C2—N6 | 1.361 (5) | C12—H12 | 0.9300 |
N3—N4 | 1.378 (5) | C13—C14 | 1.382 (7) |
N4—C5 | 1.292 (5) | C13—H13 | 0.9300 |
C5—C9 | 1.482 (6) | C14—H14 | 0.9300 |
N6—N7 | 1.412 (5) | C15—C20 | 1.349 (7) |
N6—C8 | 1.453 (6) | C15—C16 | 1.360 (8) |
N7—H71 | 0.99 (6) | C16—C17 | 1.413 (10) |
N7—H72 | 0.91 (6) | C16—H16 | 0.9300 |
C8—H8A | 0.9600 | C17—C18 | 1.306 (10) |
C8—H8B | 0.9600 | C17—H17 | 0.9300 |
C8—H8C | 0.9600 | C18—C19 | 1.324 (11) |
C9—C14 | 1.399 (6) | C18—H18 | 0.9300 |
C9—C10 | 1.396 (6) | C19—C20 | 1.377 (8) |
C10—C11 | 1.402 (6) | C19—H19 | 0.9300 |
C10—C15 | 1.482 (7) | C20—H20 | 0.9300 |
C2—S1—C5 | 86.9 (2) | C12—C11—H11 | 119.8 |
N3—C2—N6 | 123.4 (4) | C13—C12—C11 | 120.6 (5) |
N3—C2—S1 | 115.2 (3) | C13—C12—H12 | 119.7 |
N6—C2—S1 | 121.4 (3) | C11—C12—H12 | 119.7 |
C2—N3—N4 | 110.3 (3) | C12—C13—C14 | 120.0 (5) |
C5—N4—N3 | 114.9 (3) | C12—C13—H13 | 120.0 |
N4—C5—C9 | 121.5 (4) | C14—C13—H13 | 120.0 |
N4—C5—S1 | 112.6 (3) | C13—C14—C9 | 120.9 (5) |
C9—C5—S1 | 125.7 (3) | C13—C14—H14 | 119.6 |
C2—N6—N7 | 114.4 (4) | C9—C14—H14 | 119.6 |
C2—N6—C8 | 122.5 (4) | C20—C15—C16 | 116.5 (6) |
N7—N6—C8 | 119.2 (4) | C20—C15—C10 | 121.8 (6) |
N6—N7—H71 | 112 (4) | C16—C15—C10 | 121.7 (6) |
N6—N7—H72 | 104 (4) | C17—C16—C15 | 120.7 (7) |
H71—N7—H72 | 111 (5) | C17—C16—H16 | 119.7 |
N6—C8—H8A | 109.5 | C15—C16—H16 | 119.7 |
N6—C8—H8B | 109.5 | C18—C17—C16 | 119.6 (8) |
H8A—C8—H8B | 109.5 | C18—C17—H17 | 120.2 |
N6—C8—H8C | 109.5 | C16—C17—H17 | 120.2 |
H8A—C8—H8C | 109.5 | C17—C18—C19 | 121.1 (8) |
H8B—C8—H8C | 109.5 | C17—C18—H18 | 119.5 |
C14—C9—C10 | 118.7 (4) | C19—C18—H18 | 119.5 |
C14—C9—C5 | 117.1 (4) | C18—C19—C20 | 119.9 (8) |
C10—C9—C5 | 124.1 (4) | C18—C19—H19 | 120.0 |
C11—C10—C9 | 119.4 (4) | C20—C19—H19 | 120.0 |
C11—C10—C15 | 117.3 (4) | C15—C20—C19 | 122.0 (7) |
C9—C10—C15 | 123.2 (4) | C15—C20—H20 | 119.0 |
C10—C11—C12 | 120.4 (5) | C19—C20—H20 | 119.0 |
C10—C11—H11 | 119.8 |
D—H···A | D—H | H···A | D···A | D—H···A |
N7—H71···N4i | 0.99 (6) | 2.21 (7) | 3.118 (7) | 151 (5) |
N7—H72···N3ii | 0.91 (6) | 2.20 (7) | 3.100 (7) | 169 (5) |
C16—H16···N3iii | 0.93 | 2.62 | 3.534 (8) | 168 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y−1/2, −z+3/2; (iii) x, −y+1/2, z−1/2. |
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