Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100015730/qa0454sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100015730/qa0454Isup2.hkl |
CCDC reference: 156216
All H atoms were included in the refinement, at calculated positions, as riding models with C—H set to 0.95 (Ar—H) and 0.99 Å (CH2).
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); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C14H12ClNO2 | Dx = 1.462 Mg m−3 |
Mr = 261.70 | Melting point: 371 - 373 K K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.2926 (6) Å | Cell parameters from 6683 reflections |
b = 10.4429 (4) Å | θ = 2.9–27.5° |
c = 11.2028 (4) Å | µ = 0.31 mm−1 |
β = 115.829 (15)° | T = 150 K |
V = 1189.14 (9) Å3 | Prism, red |
Z = 4 | 0.20 × 0.17 × 0.10 mm |
F(000) = 544 |
Enraf Nonius KappaCCD area-detector diffractometer | 2729 independent reflections |
Radiation source: Enraf Nonius FR591 rotating anode | 1779 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.109 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.7° |
ϕ and ω scans | h = −14→14 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −13→13 |
Tmin = 0.940, Tmax = 0.969 | l = −14→14 |
18192 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0635P)2] where P = (Fo2 + 2Fc2)/3 |
2729 reflections | (Δ/σ)max < 0.001 |
163 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
C14H12ClNO2 | V = 1189.14 (9) Å3 |
Mr = 261.70 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.2926 (6) Å | µ = 0.31 mm−1 |
b = 10.4429 (4) Å | T = 150 K |
c = 11.2028 (4) Å | 0.20 × 0.17 × 0.10 mm |
β = 115.829 (15)° |
Enraf Nonius KappaCCD area-detector diffractometer | 2729 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | 1779 reflections with I > 2σ(I) |
Tmin = 0.940, Tmax = 0.969 | Rint = 0.109 |
18192 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 0.97 | Δρmax = 0.21 e Å−3 |
2729 reflections | Δρmin = −0.28 e Å−3 |
163 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.72406 (19) | 0.57168 (17) | 0.20910 (17) | 0.0340 (4) | |
O1 | 0.80999 (13) | 0.49279 (13) | 0.27202 (13) | 0.0455 (4) | |
C2 | 0.58666 (18) | 0.54950 (15) | 0.17490 (17) | 0.0311 (4) | |
Cl2 | 0.55843 (5) | 0.39676 (4) | 0.21805 (5) | 0.04187 (19) | |
C3 | 0.48609 (18) | 0.63550 (15) | 0.10887 (16) | 0.0295 (4) | |
N31 | 0.36071 (15) | 0.62397 (13) | 0.09139 (14) | 0.0333 (4) | |
C32 | 0.24495 (18) | 0.69738 (19) | −0.00469 (19) | 0.0400 (5) | |
H321 | 0.2378 | 0.6911 | −0.0958 | 0.050* | |
H322 | 0.2505 | 0.7887 | 0.0208 | 0.050* | |
C33 | 0.1295 (2) | 0.6316 (2) | 0.0057 (2) | 0.0495 (5) | |
H331 | 0.0534 | 0.6902 | −0.0198 | 0.062* | |
H332 | 0.1018 | 0.5540 | −0.0505 | 0.062* | |
C34 | 0.1864 (2) | 0.5978 (2) | 0.1514 (2) | 0.0500 (6) | |
H341 | 0.1319 | 0.5330 | 0.1688 | 0.062* | |
H342 | 0.1948 | 0.6745 | 0.2065 | 0.062* | |
C35 | 0.3197 (2) | 0.54435 (19) | 0.17666 (19) | 0.0405 (5) | |
H351 | 0.3826 | 0.5529 | 0.2713 | 0.051* | |
H352 | 0.3132 | 0.4530 | 0.1511 | 0.051* | |
C4 | 0.52273 (18) | 0.75446 (16) | 0.05398 (16) | 0.0312 (4) | |
O4 | 0.43884 (13) | 0.83136 (11) | −0.01240 (13) | 0.0410 (4) | |
C5 | 0.6960 (2) | 0.88599 (16) | 0.03419 (19) | 0.0389 (5) | |
H5 | 0.6298 | 0.9448 | −0.0189 | 0.049* | |
C6 | 0.8252 (2) | 0.90886 (18) | 0.0622 (2) | 0.0461 (5) | |
H6 | 0.8479 | 0.9830 | 0.0276 | 0.058* | |
C7 | 0.9229 (2) | 0.82417 (19) | 0.1408 (2) | 0.0476 (5) | |
H7 | 1.0123 | 0.8411 | 0.1613 | 0.060* | |
C8 | 0.88945 (19) | 0.71527 (19) | 0.1892 (2) | 0.0434 (5) | |
H8 | 0.9561 | 0.6567 | 0.2421 | 0.054* | |
C9 | 0.75917 (18) | 0.69085 (16) | 0.16107 (17) | 0.0339 (4) | |
C10 | 0.66167 (18) | 0.77668 (16) | 0.08350 (17) | 0.0312 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0365 (12) | 0.0342 (9) | 0.0304 (10) | 0.0066 (8) | 0.0137 (9) | −0.0013 (8) |
O1 | 0.0406 (8) | 0.0440 (7) | 0.0480 (8) | 0.0154 (6) | 0.0156 (7) | 0.0106 (6) |
C2 | 0.0383 (11) | 0.0274 (9) | 0.0292 (9) | 0.0021 (8) | 0.0162 (8) | 0.0017 (7) |
Cl2 | 0.0555 (4) | 0.0306 (3) | 0.0446 (3) | 0.0030 (2) | 0.0265 (3) | 0.00587 (19) |
C3 | 0.0338 (11) | 0.0302 (9) | 0.0260 (9) | 0.0006 (7) | 0.0144 (8) | −0.0036 (7) |
N31 | 0.0307 (9) | 0.0378 (8) | 0.0313 (8) | 0.0018 (6) | 0.0133 (7) | −0.0002 (7) |
C32 | 0.0324 (11) | 0.0472 (11) | 0.0353 (11) | 0.0054 (9) | 0.0100 (9) | −0.0002 (8) |
C33 | 0.0314 (12) | 0.0703 (14) | 0.0444 (12) | −0.0009 (10) | 0.0143 (10) | −0.0043 (10) |
C34 | 0.0349 (12) | 0.0737 (15) | 0.0435 (12) | −0.0062 (10) | 0.0190 (10) | −0.0048 (11) |
C35 | 0.0379 (12) | 0.0514 (12) | 0.0348 (10) | −0.0034 (9) | 0.0182 (9) | 0.0010 (9) |
C4 | 0.0381 (11) | 0.0284 (9) | 0.0288 (9) | 0.0035 (8) | 0.0161 (8) | −0.0028 (7) |
O4 | 0.0414 (8) | 0.0355 (7) | 0.0453 (8) | 0.0106 (6) | 0.0183 (7) | 0.0082 (6) |
C5 | 0.0467 (13) | 0.0322 (10) | 0.0401 (11) | −0.0013 (8) | 0.0210 (10) | −0.0011 (8) |
C6 | 0.0540 (15) | 0.0407 (11) | 0.0502 (13) | −0.0127 (10) | 0.0288 (11) | −0.0071 (9) |
C7 | 0.0376 (13) | 0.0502 (12) | 0.0579 (14) | −0.0092 (10) | 0.0234 (11) | −0.0097 (10) |
C8 | 0.0319 (12) | 0.0469 (11) | 0.0463 (12) | 0.0019 (9) | 0.0124 (10) | −0.0047 (9) |
C9 | 0.0355 (12) | 0.0344 (9) | 0.0323 (10) | 0.0013 (8) | 0.0151 (9) | −0.0041 (8) |
C10 | 0.0358 (11) | 0.0301 (9) | 0.0278 (9) | 0.0003 (8) | 0.0140 (8) | −0.0039 (7) |
C1—O1 | 1.233 (2) | C34—H341 | 0.9900 |
C1—C2 | 1.446 (3) | C34—H342 | 0.9900 |
C1—C9 | 1.477 (3) | C35—H351 | 0.9900 |
C2—C3 | 1.383 (2) | C35—H352 | 0.9900 |
C2—Cl2 | 1.7361 (17) | C4—O4 | 1.217 (2) |
C3—N31 | 1.348 (2) | C4—C10 | 1.474 (3) |
C3—C4 | 1.521 (2) | C5—C6 | 1.373 (3) |
N31—C35 | 1.484 (2) | C5—C10 | 1.395 (3) |
N31—C32 | 1.493 (2) | C5—H5 | 0.9500 |
C32—C33 | 1.523 (3) | C6—C7 | 1.389 (3) |
C32—H321 | 0.9900 | C6—H6 | 0.9500 |
C32—H322 | 0.9900 | C7—C8 | 1.381 (3) |
C33—C34 | 1.512 (3) | C7—H7 | 0.9500 |
C33—H331 | 0.9900 | C8—C9 | 1.387 (3) |
C33—H332 | 0.9900 | C8—H8 | 0.9500 |
C34—C35 | 1.513 (3) | C9—C10 | 1.392 (2) |
O1—C1—C2 | 122.06 (17) | H341—C34—H342 | 109.2 |
O1—C1—C9 | 120.12 (18) | N31—C35—C34 | 103.70 (15) |
C2—C1—C9 | 117.77 (15) | N31—C35—H351 | 111.0 |
C3—C2—C1 | 125.05 (16) | C34—C35—H351 | 111.0 |
C3—C2—Cl2 | 122.55 (15) | N31—C35—H352 | 111.0 |
C1—C2—Cl2 | 112.30 (13) | C34—C35—H352 | 111.0 |
N31—C3—C2 | 125.86 (17) | H351—C35—H352 | 109.0 |
N31—C3—C4 | 117.90 (15) | O4—C4—C10 | 120.15 (16) |
C2—C3—C4 | 116.23 (16) | O4—C4—C3 | 120.62 (17) |
C3—N31—C35 | 123.99 (15) | C10—C4—C3 | 119.22 (15) |
C3—N31—C32 | 126.39 (15) | C6—C5—C10 | 120.20 (18) |
C35—N31—C32 | 109.33 (15) | C6—C5—H5 | 119.9 |
N31—C32—C33 | 102.90 (15) | C10—C5—H5 | 119.9 |
N31—C32—H321 | 111.2 | C5—C6—C7 | 120.36 (19) |
C33—C32—H321 | 111.2 | C5—C6—H6 | 119.8 |
N31—C32—H322 | 111.2 | C7—C6—H6 | 119.8 |
C33—C32—H322 | 111.2 | C8—C7—C6 | 119.7 (2) |
H321—C32—H322 | 109.1 | C8—C7—H7 | 120.1 |
C34—C33—C32 | 102.27 (16) | C6—C7—H7 | 120.1 |
C34—C33—H331 | 111.3 | C7—C8—C9 | 120.42 (19) |
C32—C33—H331 | 111.3 | C7—C8—H8 | 119.8 |
C34—C33—H332 | 111.3 | C9—C8—H8 | 119.8 |
C32—C33—H332 | 111.3 | C8—C9—C10 | 119.71 (18) |
H331—C33—H332 | 109.2 | C8—C9—C1 | 119.91 (17) |
C33—C34—C35 | 102.05 (16) | C10—C9—C1 | 120.34 (17) |
C33—C34—H341 | 111.4 | C9—C10—C5 | 119.58 (18) |
C35—C34—H341 | 111.4 | C9—C10—C4 | 120.93 (16) |
C33—C34—H342 | 111.4 | C5—C10—C4 | 119.49 (16) |
C35—C34—H342 | 111.4 | ||
O1—C1—C2—C3 | 177.58 (17) | N31—C3—C4—C10 | 173.60 (15) |
C9—C1—C2—C3 | −5.0 (3) | C2—C3—C4—C10 | −5.3 (2) |
O1—C1—C2—Cl2 | −5.8 (2) | C10—C5—C6—C7 | −0.6 (3) |
C9—C1—C2—Cl2 | 171.59 (13) | C5—C6—C7—C8 | 1.1 (3) |
C1—C2—C3—N31 | −170.73 (16) | C6—C7—C8—C9 | −0.8 (3) |
Cl2—C2—C3—N31 | 13.0 (3) | C7—C8—C9—C10 | 0.1 (3) |
C1—C2—C3—C4 | 8.0 (3) | C7—C8—C9—C1 | 177.69 (17) |
Cl2—C2—C3—C4 | −168.27 (12) | O1—C1—C9—C8 | −1.4 (3) |
C2—C3—N31—C35 | 22.3 (3) | C2—C1—C9—C8 | −178.79 (16) |
C4—C3—N31—C35 | −156.50 (16) | O1—C1—C9—C10 | 176.27 (16) |
C2—C3—N31—C32 | −164.55 (17) | C2—C1—C9—C10 | −1.2 (2) |
C4—C3—N31—C32 | 16.7 (2) | C8—C9—C10—C5 | 0.4 (3) |
C3—N31—C32—C33 | 172.23 (16) | C1—C9—C10—C5 | −177.22 (16) |
C35—N31—C32—C33 | −13.74 (19) | C8—C9—C10—C4 | −178.88 (16) |
N31—C32—C33—C34 | 35.81 (19) | C1—C9—C10—C4 | 3.5 (3) |
C32—C33—C34—C35 | −44.7 (2) | C6—C5—C10—C9 | −0.1 (3) |
C3—N31—C35—C34 | 160.45 (16) | C6—C5—C10—C4 | 179.19 (16) |
C32—N31—C35—C34 | −13.76 (19) | O4—C4—C10—C9 | 178.93 (16) |
C33—C34—C35—N31 | 35.9 (2) | C3—C4—C10—C9 | −0.3 (2) |
N31—C3—C4—O4 | −5.6 (2) | O4—C4—C10—C5 | −0.4 (3) |
C2—C3—C4—O4 | 175.52 (16) | C3—C4—C10—C5 | −179.58 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O4i | 0.95 | 2.53 | 3.281 (2) | 136 |
C7—H7···O1ii | 0.95 | 2.41 | 3.254 (2) | 149 |
C35—H351···O4iii | 0.99 | 2.53 | 3.398 (2) | 146 |
C35—H352···Cl2 | 0.99 | 2.60 | 2.961 (2) | 101 |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+2, y+1/2, −z+1/2; (iii) x, −y+3/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H12ClNO2 |
Mr | 261.70 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 150 |
a, b, c (Å) | 11.2926 (6), 10.4429 (4), 11.2028 (4) |
β (°) | 115.829 (15) |
V (Å3) | 1189.14 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.31 |
Crystal size (mm) | 0.20 × 0.17 × 0.10 |
Data collection | |
Diffractometer | Enraf Nonius KappaCCD area-detector diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995) |
Tmin, Tmax | 0.940, 0.969 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18192, 2729, 1779 |
Rint | 0.109 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.118, 0.97 |
No. of reflections | 2729 |
No. of parameters | 163 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.28 |
Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O4i | 0.95 | 2.53 | 3.281 (2) | 135.6 |
C7—H7···O1ii | 0.95 | 2.41 | 3.254 (2) | 148.5 |
C35—H351···O4iii | 0.99 | 2.53 | 3.398 (2) | 146.4 |
C35—H352···Cl2 | 0.99 | 2.60 | 2.961 (2) | 101.4 |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+2, y+1/2, −z+1/2; (iii) x, −y+3/2, z+1/2. |
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