Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680502773X/su6228sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680502773X/su6228Isup2.hkl |
CCDC reference: 287729
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.007 Å
- R factor = 0.041
- wR factor = 0.109
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.65 mm PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C16 PLAT480_ALERT_4_C Long H...A H-Bond Reported H1N .. BR1 .. 3.11 Ang.
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 67.96 From the CIF: _reflns_number_total 2997 Count of symmetry unique reflns 1779 Completeness (_total/calc) 168.47% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1218 Fraction of Friedel pairs measured 0.685 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 4 ALERT type 4 Improvement, methodology, query or suggestion
Compound (I) was prepared according to the literature procedure (Xue et al., 2000). Suitable crystals were obtained by recrystallization from methanol-dichloromethane (1:1).
The H atoms were included in idealized positions and refined as riding atoms with Uiso(H) = 1.2Ueq(parent atom), and N—H = 0.86 Å and C—H = 0.93 Å (0.96 Å for methyl groups).
Data collection: Nonius Diffractometer Control Software (Nonius, 1996); cell refinement: Nonius Diffractometer Control Software; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
Fig. 1. Molecular structure of (I), showing the atom labeling and displacement ellipsoids drawn at the 50% probability level. | |
Fig. 2. The packing of (I), with hydrogen bonding shown as dashed lines. |
C16H12Br2N2O2S | F(000) = 896 |
Mr = 456.16 | Dx = 1.825 Mg m−3 |
Orthorhombic, P212121 | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
a = 4.939 (1) Å | θ = 5.3–18.8° |
b = 16.595 (3) Å | µ = 7.46 mm−1 |
c = 20.254 (4) Å | T = 299 K |
V = 1660.1 (6) Å3 | Long needle, light brown |
Z = 4 | 0.65 × 0.08 × 0.05 mm |
Nonius CAD-4 diffractometer | 2758 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.019 |
Graphite monochromator | θmax = 68.0°, θmin = 3.4° |
ω/2θ scans | h = 0→5 |
Absorption correction: psi-scan (North et al., 1968) | k = 0→19 |
Tmin = 0.486, Tmax = 0.708 | l = −24→24 |
3465 measured reflections | 3 standard reflections every 120 min |
2997 independent reflections | intensity decay: 1.0% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.041 | w = 1/[σ2(Fo2) + (0.076P)2 + 0.4357P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.109 | (Δ/σ)max < 0.001 |
S = 1.08 | Δρmax = 0.69 e Å−3 |
2997 reflections | Δρmin = −0.92 e Å−3 |
209 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0012 (2) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.01 (3) |
C16H12Br2N2O2S | V = 1660.1 (6) Å3 |
Mr = 456.16 | Z = 4 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 4.939 (1) Å | µ = 7.46 mm−1 |
b = 16.595 (3) Å | T = 299 K |
c = 20.254 (4) Å | 0.65 × 0.08 × 0.05 mm |
Nonius CAD-4 diffractometer | 2758 reflections with I > 2σ(I) |
Absorption correction: psi-scan (North et al., 1968) | Rint = 0.019 |
Tmin = 0.486, Tmax = 0.708 | 3 standard reflections every 120 min |
3465 measured reflections | intensity decay: 1.0% |
2997 independent reflections |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.109 | Δρmax = 0.69 e Å−3 |
S = 1.08 | Δρmin = −0.92 e Å−3 |
2997 reflections | Absolute structure: Flack (1983) |
209 parameters | Absolute structure parameter: −0.01 (3) |
0 restraints |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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 | ||
Br1 | 0.67032 (15) | 0.06168 (3) | 0.17545 (3) | 0.0739 (2) | |
Br2 | 0.72224 (16) | 0.34697 (5) | 0.03074 (3) | 0.0822 (3) | |
S1 | 0.45127 (18) | 0.15331 (5) | 0.33555 (5) | 0.0360 (3) | |
O1 | 0.7323 (5) | 0.14564 (17) | 0.31743 (15) | 0.0460 (8) | |
O2 | 0.3241 (7) | 0.09229 (18) | 0.37390 (16) | 0.0534 (10) | |
N1 | 0.2761 (6) | 0.15936 (18) | 0.26682 (15) | 0.0364 (9) | |
N2 | 0.0963 (8) | 0.3138 (2) | 0.24236 (19) | 0.0459 (11) | |
C1 | 0.3804 (8) | 0.2041 (2) | 0.21271 (19) | 0.0368 (10) | |
C2 | 0.5625 (10) | 0.1704 (3) | 0.1682 (2) | 0.0470 (12) | |
C3 | 0.6661 (11) | 0.2144 (3) | 0.1149 (2) | 0.0543 (16) | |
C4 | 0.5827 (10) | 0.2916 (3) | 0.1050 (2) | 0.0510 (16) | |
C5 | 0.3953 (9) | 0.3298 (2) | 0.1475 (2) | 0.0443 (12) | |
C6 | 0.3020 (13) | 0.4095 (3) | 0.1402 (2) | 0.0600 (14) | |
C7 | 0.1102 (12) | 0.4385 (3) | 0.1829 (3) | 0.0650 (16) | |
C8 | 0.0162 (12) | 0.3887 (3) | 0.2315 (3) | 0.0603 (17) | |
C9 | 0.2905 (8) | 0.2838 (2) | 0.20064 (19) | 0.0397 (11) | |
C10 | 0.4153 (8) | 0.2452 (2) | 0.37766 (18) | 0.0369 (10) | |
C11 | 0.5991 (9) | 0.3069 (3) | 0.3663 (2) | 0.0470 (12) | |
C12 | 0.5790 (11) | 0.3769 (3) | 0.4025 (2) | 0.0537 (16) | |
C13 | 0.3806 (11) | 0.3870 (3) | 0.4501 (2) | 0.0553 (16) | |
C14 | 0.1963 (11) | 0.3243 (3) | 0.4598 (2) | 0.0581 (15) | |
C15 | 0.2108 (9) | 0.2538 (3) | 0.4241 (2) | 0.0483 (12) | |
C16 | 0.3710 (16) | 0.4613 (4) | 0.4915 (3) | 0.080 (2) | |
H1N | 0.12190 | 0.13560 | 0.26360 | 0.0440* | |
H3 | 0.79130 | 0.19110 | 0.08650 | 0.0650* | |
H6 | 0.37000 | 0.44210 | 0.10680 | 0.0720* | |
H7 | 0.04530 | 0.49090 | 0.17890 | 0.0780* | |
H8 | −0.11600 | 0.40930 | 0.25950 | 0.0720* | |
H11 | 0.73420 | 0.30100 | 0.33470 | 0.0560* | |
H12 | 0.70150 | 0.41840 | 0.39470 | 0.0650* | |
H14 | 0.06040 | 0.33020 | 0.49120 | 0.0700* | |
H15 | 0.08570 | 0.21280 | 0.43090 | 0.0580* | |
H16A | 0.34950 | 0.50760 | 0.46360 | 0.0960* | |
H16B | 0.53630 | 0.46610 | 0.51610 | 0.0960* | |
H16C | 0.22090 | 0.45800 | 0.52150 | 0.0960* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.1012 (5) | 0.0548 (3) | 0.0657 (3) | 0.0222 (3) | 0.0097 (3) | −0.0118 (2) |
Br2 | 0.0905 (5) | 0.1038 (5) | 0.0522 (3) | −0.0254 (4) | 0.0097 (3) | 0.0225 (3) |
S1 | 0.0288 (4) | 0.0363 (4) | 0.0428 (5) | 0.0004 (3) | 0.0020 (3) | 0.0059 (4) |
O1 | 0.0222 (12) | 0.0534 (15) | 0.0623 (16) | 0.0042 (11) | 0.0014 (12) | −0.0051 (13) |
O2 | 0.0516 (18) | 0.0503 (15) | 0.0582 (17) | −0.0002 (14) | 0.0007 (15) | 0.0177 (14) |
N1 | 0.0285 (15) | 0.0374 (15) | 0.0434 (15) | −0.0033 (13) | −0.0042 (13) | 0.0023 (13) |
N2 | 0.0404 (19) | 0.0442 (18) | 0.053 (2) | 0.0040 (15) | −0.0017 (16) | 0.0005 (15) |
C1 | 0.0359 (19) | 0.0389 (18) | 0.0355 (17) | −0.0026 (15) | −0.0017 (15) | −0.0044 (14) |
C2 | 0.052 (2) | 0.045 (2) | 0.044 (2) | 0.0047 (18) | 0.003 (2) | −0.0028 (18) |
C3 | 0.058 (3) | 0.064 (3) | 0.041 (2) | 0.000 (2) | 0.010 (2) | −0.0023 (19) |
C4 | 0.053 (3) | 0.065 (3) | 0.035 (2) | −0.012 (2) | −0.0020 (18) | 0.0078 (19) |
C5 | 0.047 (2) | 0.042 (2) | 0.044 (2) | −0.0095 (16) | −0.0116 (17) | 0.0056 (16) |
C6 | 0.074 (3) | 0.051 (2) | 0.055 (2) | −0.012 (2) | −0.011 (3) | 0.017 (2) |
C7 | 0.075 (3) | 0.043 (2) | 0.077 (3) | 0.004 (2) | −0.019 (3) | 0.009 (2) |
C8 | 0.063 (3) | 0.049 (3) | 0.069 (3) | 0.007 (2) | −0.003 (3) | 0.000 (2) |
C9 | 0.0370 (19) | 0.0425 (19) | 0.0397 (18) | −0.0062 (17) | −0.0089 (16) | 0.0006 (15) |
C10 | 0.0319 (18) | 0.0452 (19) | 0.0336 (17) | 0.0004 (15) | −0.0018 (14) | 0.0053 (15) |
C11 | 0.041 (2) | 0.048 (2) | 0.052 (2) | −0.0017 (18) | 0.0074 (18) | 0.0003 (18) |
C12 | 0.052 (3) | 0.050 (2) | 0.059 (3) | −0.002 (2) | −0.006 (2) | −0.004 (2) |
C13 | 0.068 (3) | 0.056 (3) | 0.042 (2) | 0.019 (2) | −0.013 (2) | −0.0046 (19) |
C14 | 0.056 (3) | 0.081 (3) | 0.0374 (19) | 0.010 (3) | 0.007 (2) | −0.002 (2) |
C15 | 0.037 (2) | 0.062 (2) | 0.046 (2) | 0.0037 (19) | 0.0098 (18) | 0.0038 (19) |
C16 | 0.107 (5) | 0.071 (3) | 0.061 (3) | 0.024 (3) | −0.015 (3) | −0.019 (3) |
Br1—C2 | 1.887 (5) | C10—C15 | 1.388 (6) |
Br2—C4 | 1.893 (4) | C10—C11 | 1.388 (6) |
S1—O1 | 1.441 (3) | C11—C12 | 1.377 (7) |
S1—O2 | 1.422 (3) | C12—C13 | 1.385 (7) |
S1—N1 | 1.642 (3) | C13—C16 | 1.492 (8) |
S1—C10 | 1.756 (4) | C13—C14 | 1.396 (7) |
N1—C1 | 1.421 (5) | C14—C15 | 1.377 (7) |
N2—C8 | 1.323 (6) | C3—H3 | 0.9300 |
N2—C9 | 1.372 (5) | C6—H6 | 0.9300 |
N1—H1N | 0.8600 | C7—H7 | 0.9300 |
C1—C2 | 1.391 (6) | C8—H8 | 0.9300 |
C1—C9 | 1.416 (5) | C11—H11 | 0.9300 |
C2—C3 | 1.400 (6) | C12—H12 | 0.9300 |
C3—C4 | 1.361 (7) | C14—H14 | 0.9300 |
C4—C5 | 1.414 (6) | C15—H15 | 0.9300 |
C5—C6 | 1.408 (6) | C16—H16A | 0.9600 |
C5—C9 | 1.417 (5) | C16—H16B | 0.9600 |
C6—C7 | 1.370 (8) | C16—H16C | 0.9600 |
C7—C8 | 1.367 (8) | ||
Br1···S1 | 3.7413 (14) | C15···C14vii | 3.600 (7) |
Br1···O1 | 3.210 (3) | C8···H11v | 2.9000 |
Br1···N1 | 3.137 (3) | C10···H14vii | 3.0200 |
Br1···C7i | 3.686 (6) | C11···H8ii | 3.0900 |
Br1···C12i | 3.662 (5) | C12···H14ii | 3.0800 |
Br1···H1Nii | 3.1100 | C13···H15vii | 3.0900 |
Br1···H16Ai | 2.9600 | C14···H15vii | 3.0000 |
Br2···H6 | 2.8100 | C15···H11v | 3.0700 |
S1···Br1 | 3.7413 (14) | C15···H14vii | 2.8000 |
O1···Br1 | 3.210 (3) | C16···H6viii | 3.0700 |
O1···N1ii | 2.884 (4) | H1N···Br1v | 3.1100 |
O1···C2 | 3.164 (5) | H1N···O1v | 2.2200 |
O1···H1Nii | 2.2200 | H6···Br2 | 2.8100 |
O1···H11 | 2.6000 | H6···C16ix | 3.0700 |
O1···H7i | 2.7900 | H6···H16Cix | 2.4400 |
O2···H15 | 2.5900 | H7···O1vi | 2.7900 |
O2···H16Biii | 2.8100 | H7···O2x | 2.7000 |
O2···H7iv | 2.7000 | H8···C11v | 3.0900 |
N1···Br1 | 3.137 (3) | H8···H11v | 2.4700 |
N1···O1v | 2.884 (4) | H11···O1 | 2.6000 |
N1···N2 | 2.757 (5) | H11···N2ii | 2.6000 |
N2···N1 | 2.757 (5) | H11···C8ii | 2.9000 |
N2···C10 | 3.360 (5) | H11···C15ii | 3.0700 |
N2···H11v | 2.6000 | H11···H8ii | 2.4700 |
C2···O1 | 3.164 (5) | H14···C12v | 3.0800 |
C7···Br1vi | 3.686 (6) | H14···H16C | 2.3500 |
C10···N2 | 3.360 (5) | H14···C10iii | 3.0200 |
C11···C14ii | 3.517 (7) | H14···C15iii | 2.8000 |
C11···C15ii | 3.358 (6) | H15···O2 | 2.5900 |
C12···Br1vi | 3.662 (5) | H15···C13iii | 3.0900 |
C12···C14ii | 3.377 (7) | H15···C14iii | 3.0000 |
C14···C15iii | 3.600 (7) | H16A···Br1vi | 2.9600 |
C14···C11v | 3.517 (7) | H16B···O2vii | 2.8100 |
C14···C12v | 3.377 (7) | H16C···H14 | 2.3500 |
C15···C11v | 3.358 (6) | H16C···H6viii | 2.4400 |
O1—S1—O2 | 120.09 (19) | S1—C10—C15 | 119.5 (3) |
O1—S1—N1 | 107.27 (17) | C10—C11—C12 | 119.1 (4) |
O1—S1—C10 | 107.32 (18) | C11—C12—C13 | 121.6 (5) |
O2—S1—N1 | 105.89 (18) | C12—C13—C16 | 120.9 (5) |
O2—S1—C10 | 107.96 (18) | C12—C13—C14 | 118.0 (4) |
N1—S1—C10 | 107.78 (17) | C14—C13—C16 | 121.1 (5) |
S1—N1—C1 | 119.7 (3) | C13—C14—C15 | 121.7 (4) |
C8—N2—C9 | 116.6 (4) | C10—C15—C14 | 118.8 (4) |
C1—N1—H1N | 120.00 | C2—C3—H3 | 120.00 |
S1—N1—H1N | 120.00 | C4—C3—H3 | 120.00 |
C2—C1—C9 | 117.8 (4) | C5—C6—H6 | 120.00 |
N1—C1—C9 | 120.5 (3) | C7—C6—H6 | 120.00 |
N1—C1—C2 | 121.6 (3) | C6—C7—H7 | 121.00 |
Br1—C2—C1 | 121.1 (3) | C8—C7—H7 | 121.00 |
Br1—C2—C3 | 117.1 (3) | N2—C8—H8 | 117.00 |
C1—C2—C3 | 121.8 (4) | C7—C8—H8 | 117.00 |
C2—C3—C4 | 119.6 (4) | C10—C11—H11 | 120.00 |
C3—C4—C5 | 122.0 (4) | C12—C11—H11 | 120.00 |
Br2—C4—C3 | 117.7 (3) | C11—C12—H12 | 119.00 |
Br2—C4—C5 | 120.3 (3) | C13—C12—H12 | 119.00 |
C4—C5—C6 | 124.8 (4) | C13—C14—H14 | 119.00 |
C4—C5—C9 | 117.4 (3) | C15—C14—H14 | 119.00 |
C6—C5—C9 | 117.8 (4) | C10—C15—H15 | 121.00 |
C5—C6—C7 | 119.3 (4) | C14—C15—H15 | 121.00 |
C6—C7—C8 | 118.5 (5) | C13—C16—H16A | 110.00 |
N2—C8—C7 | 125.9 (5) | C13—C16—H16B | 109.00 |
N2—C9—C5 | 121.8 (3) | C13—C16—H16C | 109.00 |
C1—C9—C5 | 121.3 (3) | H16A—C16—H16B | 109.00 |
N2—C9—C1 | 116.9 (3) | H16A—C16—H16C | 109.00 |
C11—C10—C15 | 120.9 (4) | H16B—C16—H16C | 109.00 |
S1—C10—C11 | 119.6 (3) | ||
O1—S1—N1—C1 | −38.8 (3) | C2—C3—C4—Br2 | −178.3 (4) |
O2—S1—N1—C1 | −168.2 (3) | C2—C3—C4—C5 | 0.7 (7) |
C10—S1—N1—C1 | 76.5 (3) | Br2—C4—C5—C9 | 177.5 (3) |
N1—S1—C10—C11 | −90.6 (3) | C3—C4—C5—C9 | −1.5 (7) |
O1—S1—C10—C15 | −152.4 (3) | Br2—C4—C5—C6 | −1.3 (7) |
O2—S1—C10—C15 | −21.6 (4) | C3—C4—C5—C6 | 179.7 (5) |
N1—S1—C10—C15 | 92.4 (3) | C6—C5—C9—N2 | 2.7 (6) |
O1—S1—C10—C11 | 24.7 (4) | C6—C5—C9—C1 | −177.9 (4) |
O2—S1—C10—C11 | 155.5 (3) | C4—C5—C6—C7 | 176.9 (5) |
S1—N1—C1—C2 | 84.2 (4) | C9—C5—C6—C7 | −1.9 (7) |
S1—N1—C1—C9 | −99.0 (4) | C4—C5—C9—C1 | 3.2 (6) |
C8—N2—C9—C1 | 179.0 (4) | C4—C5—C9—N2 | −176.2 (4) |
C8—N2—C9—C5 | −1.6 (6) | C5—C6—C7—C8 | 0.2 (8) |
C9—N2—C8—C7 | −0.3 (8) | C6—C7—C8—N2 | 1.0 (9) |
N1—C1—C9—N2 | −1.5 (5) | S1—C10—C15—C14 | 175.8 (3) |
N1—C1—C9—C5 | 179.0 (4) | C15—C10—C11—C12 | 0.9 (6) |
C9—C1—C2—C3 | 3.2 (6) | S1—C10—C11—C12 | −176.1 (3) |
C2—C1—C9—C5 | −4.0 (6) | C11—C10—C15—C14 | −1.2 (6) |
N1—C1—C2—Br1 | 2.5 (6) | C10—C11—C12—C13 | 0.3 (7) |
C2—C1—C9—N2 | 175.4 (4) | C11—C12—C13—C14 | −1.1 (7) |
N1—C1—C2—C3 | −179.9 (4) | C11—C12—C13—C16 | 176.5 (5) |
C9—C1—C2—Br1 | −174.4 (3) | C16—C13—C14—C15 | −176.9 (5) |
Br1—C2—C3—C4 | 176.1 (4) | C12—C13—C14—C15 | 0.8 (7) |
C1—C2—C3—C4 | −1.6 (7) | C13—C14—C15—C10 | 0.4 (7) |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x+1, y, z; (iii) x−1/2, −y+1/2, −z+1; (iv) −x, y−1/2, −z+1/2; (v) x−1, y, z; (vi) −x+1, y+1/2, −z+1/2; (vii) x+1/2, −y+1/2, −z+1; (viii) −x+1/2, −y+1, z+1/2; (ix) −x+1/2, −y+1, z−1/2; (x) −x, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1v | 0.86 | 2.22 | 2.884 (4) | 134 |
N1—H1N···Br1v | 0.86 | 3.11 | 3.873 (3) | 149 |
C6—H6···Br2 | 0.93 | 2.81 | 3.209 (5) | 107 |
C11—H11···N2ii | 0.93 | 2.60 | 3.514 (6) | 169 |
C15—H15···O2 | 0.93 | 2.59 | 2.921 (6) | 101 |
Symmetry codes: (ii) x+1, y, z; (v) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C16H12Br2N2O2S |
Mr | 456.16 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 299 |
a, b, c (Å) | 4.939 (1), 16.595 (3), 20.254 (4) |
V (Å3) | 1660.1 (6) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 7.46 |
Crystal size (mm) | 0.65 × 0.08 × 0.05 |
Data collection | |
Diffractometer | Nonius CAD-4 diffractometer |
Absorption correction | Psi-scan (North et al., 1968) |
Tmin, Tmax | 0.486, 0.708 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3465, 2997, 2758 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.601 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.109, 1.08 |
No. of reflections | 2997 |
No. of parameters | 209 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.69, −0.92 |
Absolute structure | Flack (1983) |
Absolute structure parameter | −0.01 (3) |
Computer programs: Nonius Diffractometer Control Software (Nonius, 1996), Nonius Diffractometer Control Software, REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.86 | 2.22 | 2.884 (4) | 134 |
N1—H1N···Br1i | 0.86 | 3.11 | 3.873 (3) | 149 |
Symmetry code: (i) x−1, y, z. |
The investigation of the crystal structure of the title compound, (I), is part of our search for Zinquin Ester analogues (Kimber et al., 2000). This class of the compounds has been shown to be effective in the detection of zinc (II) in a range of mammalian cells (Pearce et al., 2001).
The molecular structure of the title compound (I) is illustrated in Fig. 1. The quinoline ring system is planar and inclined to the phenyl ring of the tosyl moiety [torsion angle C1—N1—S1—C10 being 76.5 (3)°].
The crystal packing of (I) is stabilized through a hydrogen-bonding network, as shown in Fig. 2. Details of the hydrogen bonding are given in Table 1. The H atom of the NH group has an intermolecular contact to atom O1, with an H···O distance of 2.22 Å, and is also connected to the bromine atom, indicating very weak N—H···Br hydrogen bonding, with an H···Br distance of 3.11 Å.