Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801001404/ci6006sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801001404/ci6006Isup2.hkl |
CCDC reference: 159748
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.004 Å
- R factor = 0.052
- wR factor = 0.131
- Data-to-parameter ratio = 15.2
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.47 From the CIF: _reflns_number_total 2076 Count of symmetry unique reflns 1285 Completeness (_total/calc) 161.56% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 791 Fraction of Friedel pairs measured 0.616 Are heavy atom types Z>Si present yes 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.
The title compound, (I), was prepared by Spa Contract Synthesis. Crystals of (I) were grown from an acetone solution.
All H atoms were included in the refinement at calculated positions as riding models with C—H set to 0.95 (Ar—H) and 0.98 Å (CH3). The number of Friedel pairs is 560.
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.
Fig. 1. The molecular configuration and atom numbering scheme for (I), showing 50% probability ellipsoids. |
C11H8ClNO2 | Dx = 1.499 Mg m−3 |
Mr = 221.63 | Melting point: 413-413.5 K K |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.473 (2) Å | Cell parameters from 4247 reflections |
b = 24.303 (5) Å | θ = 2.9–39.4° |
c = 3.8594 (8) Å | µ = 0.36 mm−1 |
V = 982.3 (3) Å3 | T = 150 K |
Z = 4 | Needle, yellow |
F(000) = 456 | 0.55 × 0.05 × 0.05 mm |
Enraf Nonius KappaCCD area-detector diffractometer | 2076 independent reflections |
Radiation source: Enraf Nonius FR591 rotating anode | 1583 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.091 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.2° |
ϕ and ω scans | h = 0→13 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = 0→31 |
Tmin = 0.825, Tmax = 0.982 | l = −4→4 |
6579 measured reflections |
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)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.131 | w = 1/[σ2(Fo2) + (0.0742P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
2076 reflections | Δρmax = 0.49 e Å−3 |
137 parameters | Δρmin = −0.37 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.28 (11) |
C11H8ClNO2 | V = 982.3 (3) Å3 |
Mr = 221.63 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 10.473 (2) Å | µ = 0.36 mm−1 |
b = 24.303 (5) Å | T = 150 K |
c = 3.8594 (8) Å | 0.55 × 0.05 × 0.05 mm |
Enraf Nonius KappaCCD area-detector diffractometer | 2076 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | 1583 reflections with I > 2σ(I) |
Tmin = 0.825, Tmax = 0.982 | Rint = 0.091 |
6579 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.131 | Δρmax = 0.49 e Å−3 |
S = 1.00 | Δρmin = −0.37 e Å−3 |
2076 reflections | Absolute structure: Flack (1983) |
137 parameters | Absolute structure parameter: 0.28 (11) |
1 restraint |
Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. |
Geometry. Mean plane data ex SHELXL97 ########################### Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 0.9742 (0.0184) x + 9.8588 (0.0416) y + 3.5093 (0.0032) z = 6.8087 (0.0172) * 0.0050 (0.0021) N1 * -0.0016 (0.0021) C2 * -0.0025 (0.0024) C3 * 0.0054 (0.0024) C4 * -0.0062 (0.0021) C5 Rms deviation of fitted atoms = 0.0045 2.9354 (0.0144) x + 8.5212 (0.0291) y - 3.4487 (0.0025) z = 2.0297 (0.0144) Angle to previous plane (with approximate e.s.d.) = 49.89 (0.09) * 0.0015 (0.0022) C6 * 0.0015 (0.0023) C7 * -0.0036 (0.0023) C8 * 0.0027 (0.0023) C9 * 0.0002 (0.0026) C10 * -0.0023 (0.0024) C11 Rms deviation of fitted atoms = 0.0022 |
x | y | z | Uiso*/Ueq | ||
N1 | 0.6048 (3) | 0.34814 (10) | 0.7957 (7) | 0.0263 (7) | |
C2 | 0.6172 (3) | 0.29531 (13) | 0.9388 (9) | 0.0265 (7) | |
O2 | 0.5295 (2) | 0.26786 (9) | 1.0459 (7) | 0.0329 (6) | |
C3 | 0.7553 (3) | 0.28254 (13) | 0.9360 (10) | 0.0300 (8) | |
H3 | 0.7927 | 0.2493 | 1.0174 | 0.038* | |
C4 | 0.8180 (3) | 0.32409 (15) | 0.8042 (9) | 0.0358 (9) | |
H4 | 0.9080 | 0.3260 | 0.7769 | 0.045* | |
C5 | 0.7259 (3) | 0.36778 (15) | 0.7037 (10) | 0.0334 (8) | |
O5 | 0.7472 (2) | 0.41149 (10) | 0.5664 (8) | 0.0452 (7) | |
C6 | 0.4875 (3) | 0.37742 (12) | 0.7585 (9) | 0.0234 (7) | |
C7 | 0.3849 (3) | 0.35109 (12) | 0.6061 (8) | 0.0242 (7) | |
H7 | 0.3931 | 0.3145 | 0.5218 | 0.030* | |
C8 | 0.2704 (3) | 0.37884 (12) | 0.5787 (8) | 0.0241 (7) | |
Cl8 | 0.14304 (7) | 0.34360 (3) | 0.3922 (3) | 0.0320 (2) | |
C9 | 0.2546 (3) | 0.43270 (13) | 0.6965 (8) | 0.0262 (7) | |
C10 | 0.3599 (3) | 0.45747 (13) | 0.8481 (9) | 0.0257 (7) | |
H10 | 0.3522 | 0.4941 | 0.9320 | 0.032* | |
C11 | 0.4767 (3) | 0.43050 (11) | 0.8816 (10) | 0.0275 (7) | |
H11 | 0.5474 | 0.4483 | 0.9871 | 0.034* | |
C12 | 0.1308 (3) | 0.46269 (16) | 0.6597 (10) | 0.0355 (9) | |
H121 | 0.1087 | 0.4657 | 0.4137 | 0.044* | |
H122 | 0.1390 | 0.4996 | 0.7594 | 0.044* | |
H123 | 0.0635 | 0.4425 | 0.7819 | 0.044* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0243 (15) | 0.0187 (14) | 0.0359 (19) | 0.0001 (10) | 0.0013 (11) | 0.0037 (11) |
C2 | 0.0348 (19) | 0.0190 (16) | 0.0258 (18) | 0.0012 (14) | 0.0020 (14) | −0.0002 (14) |
O2 | 0.0312 (13) | 0.0221 (12) | 0.0455 (13) | −0.0001 (11) | 0.0054 (10) | 0.0060 (10) |
C3 | 0.0289 (17) | 0.0222 (16) | 0.039 (2) | 0.0068 (14) | −0.0007 (15) | 0.0023 (14) |
C4 | 0.0275 (19) | 0.032 (2) | 0.048 (3) | 0.0034 (15) | 0.0025 (15) | 0.0066 (16) |
C5 | 0.033 (2) | 0.0281 (19) | 0.0394 (19) | −0.0001 (16) | 0.0007 (16) | 0.0051 (15) |
O5 | 0.0360 (15) | 0.0275 (14) | 0.0722 (19) | −0.0013 (11) | 0.0068 (14) | 0.0197 (13) |
C6 | 0.0239 (17) | 0.0203 (15) | 0.0262 (16) | 0.0023 (14) | 0.0019 (13) | 0.0037 (11) |
C7 | 0.0286 (18) | 0.0196 (17) | 0.0243 (18) | 0.0000 (13) | 0.0019 (13) | 0.0002 (13) |
C8 | 0.0267 (17) | 0.0224 (16) | 0.0233 (16) | −0.0044 (14) | 0.0001 (13) | 0.0003 (12) |
Cl8 | 0.0281 (4) | 0.0350 (4) | 0.0330 (4) | −0.0040 (3) | −0.0014 (4) | −0.0035 (4) |
C9 | 0.0299 (19) | 0.0240 (17) | 0.0248 (17) | 0.0024 (14) | 0.0049 (14) | 0.0037 (14) |
C10 | 0.0317 (18) | 0.0184 (14) | 0.0269 (19) | 0.0018 (13) | 0.0062 (13) | 0.0015 (13) |
C11 | 0.0324 (17) | 0.0215 (15) | 0.0286 (16) | −0.0042 (13) | 0.0000 (16) | 0.0009 (15) |
C12 | 0.040 (2) | 0.029 (2) | 0.037 (2) | 0.0099 (16) | −0.0013 (15) | 0.0003 (14) |
N1—C5 | 1.401 (4) | C7—C8 | 1.380 (4) |
N1—C2 | 1.404 (4) | C7—H7 | 0.95 |
N1—C6 | 1.427 (4) | C8—C9 | 1.396 (4) |
C2—O2 | 1.208 (4) | C8—Cl8 | 1.741 (3) |
C2—C3 | 1.480 (4) | C9—C10 | 1.386 (5) |
C3—C4 | 1.307 (5) | C9—C12 | 1.494 (4) |
C3—H3 | 0.95 | C10—C11 | 1.393 (4) |
C4—C5 | 1.486 (5) | C10—H10 | 0.95 |
C4—H4 | 0.95 | C11—H11 | 0.95 |
C5—O5 | 1.208 (4) | C12—H121 | 0.98 |
C6—C11 | 1.380 (4) | C12—H122 | 0.98 |
C6—C7 | 1.382 (5) | C12—H123 | 0.98 |
C5—N1—C2 | 109.1 (3) | C6—C7—H7 | 120.6 |
C5—N1—C6 | 125.7 (3) | C7—C8—C9 | 122.4 (3) |
C2—N1—C6 | 125.1 (3) | C7—C8—Cl8 | 117.2 (2) |
O2—C2—N1 | 124.7 (3) | C9—C8—Cl8 | 120.4 (2) |
O2—C2—C3 | 129.0 (3) | C10—C9—C8 | 116.8 (3) |
N1—C2—C3 | 106.2 (3) | C10—C9—C12 | 121.2 (3) |
C4—C3—C2 | 109.4 (3) | C8—C9—C12 | 121.9 (3) |
C4—C3—H3 | 125.3 | C9—C10—C11 | 122.2 (3) |
C2—C3—H3 | 125.3 | C9—C10—H10 | 118.9 |
C3—C4—C5 | 109.2 (3) | C11—C10—H10 | 118.9 |
C3—C4—H4 | 125.4 | C6—C11—C10 | 118.7 (3) |
C5—C4—H4 | 125.4 | C6—C11—H11 | 120.6 |
O5—C5—N1 | 125.3 (3) | C10—C11—H11 | 120.6 |
O5—C5—C4 | 128.6 (3) | C9—C12—H121 | 109.5 |
N1—C5—C4 | 106.1 (3) | C9—C12—H122 | 109.5 |
C11—C6—C7 | 121.0 (3) | H121—C12—H122 | 109.5 |
C11—C6—N1 | 120.2 (3) | C9—C12—H123 | 109.5 |
C7—C6—N1 | 118.8 (3) | H121—C12—H123 | 109.5 |
C8—C7—C6 | 118.8 (3) | H122—C12—H123 | 109.5 |
C8—C7—H7 | 120.6 | ||
C5—N1—C2—O2 | 179.2 (3) | C5—N1—C6—C7 | 131.6 (3) |
C6—N1—C2—O2 | 0.6 (5) | C2—N1—C6—C7 | −50.0 (5) |
C5—N1—C2—C3 | 0.6 (4) | C11—C6—C7—C8 | 0.0 (5) |
C6—N1—C2—C3 | −178.0 (3) | N1—C6—C7—C8 | 178.2 (3) |
O2—C2—C3—C4 | −178.4 (4) | C6—C7—C8—C9 | 0.6 (5) |
N1—C2—C3—C4 | 0.1 (4) | C6—C7—C8—Cl8 | −178.9 (2) |
C2—C3—C4—C5 | −0.8 (4) | C7—C8—C9—C10 | −0.7 (5) |
C2—N1—C5—O5 | 178.1 (4) | Cl8—C8—C9—C10 | 178.7 (3) |
C6—N1—C5—O5 | −3.3 (6) | C7—C8—C9—C12 | 178.9 (3) |
C2—N1—C5—C4 | −1.0 (4) | Cl8—C8—C9—C12 | −1.7 (4) |
C6—N1—C5—C4 | 177.6 (3) | C8—C9—C10—C11 | 0.3 (5) |
C3—C4—C5—O5 | −178.0 (4) | C12—C9—C10—C11 | −179.3 (3) |
C3—C4—C5—N1 | 1.1 (4) | C7—C6—C11—C10 | −0.3 (5) |
C5—N1—C6—C11 | −50.1 (5) | N1—C6—C11—C10 | −178.6 (3) |
C2—N1—C6—C11 | 128.3 (3) | C9—C10—C11—C6 | 0.2 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O2i | 0.95 | 2.52 | 3.150 (4) | 124 |
C7—H7···O2ii | 0.95 | 2.59 | 3.325 (4) | 135 |
C10—H10···O5iii | 0.95 | 2.57 | 3.480 (4) | 160 |
Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) x, y, z−1; (iii) −x+1, −y+1, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C11H8ClNO2 |
Mr | 221.63 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 150 |
a, b, c (Å) | 10.473 (2), 24.303 (5), 3.8594 (8) |
V (Å3) | 982.3 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.36 |
Crystal size (mm) | 0.55 × 0.05 × 0.05 |
Data collection | |
Diffractometer | Enraf Nonius KappaCCD area-detector diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995) |
Tmin, Tmax | 0.825, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6579, 2076, 1583 |
Rint | 0.091 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.131, 1.00 |
No. of reflections | 2076 |
No. of parameters | 137 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.49, −0.37 |
Absolute structure | Flack (1983) |
Absolute structure parameter | 0.28 (11) |
Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON97 (Spek, 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O2i | 0.95 | 2.52 | 3.150 (4) | 124 |
C7—H7···O2ii | 0.95 | 2.59 | 3.325 (4) | 135 |
C10—H10···O5iii | 0.95 | 2.57 | 3.480 (4) | 160 |
Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) x, y, z−1; (iii) −x+1, −y+1, z+1/2. |
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