Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055742/hb2615sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055742/hb2615Isup2.hkl |
CCDC reference: 674080
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- R factor = 0.034
- wR factor = 0.090
- Data-to-parameter ratio = 12.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.01 PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.06
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 25.02 From the CIF: _reflns_number_total 2181 Count of symmetry unique reflns 1230 Completeness (_total/calc) 177.32% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 951 Fraction of Friedel pairs measured 0.773 Are heavy atom types Z>Si present yes PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
A mixture of 4-chloroaniline (10.0 g, 65.7 mmol), 2-nitrobenzoyl chloride (10 ml, 86.9 mmol) and pyridine (20 ml) was left at 298 K for 15 h. Water (100 ml) was then added, and the resulting precipitate was collected. Recrystallization from benzene gave 12.6 g (75%) of (I) as yellow needles: mp 368–369 K, 1H NMR (CDCl3) δ 7.23–8.30 (m, 8H, Ar—Hs), 11.36 (br s, 1H, NH).
All H atoms were located in a difference map. Those bonded to C were relocated in idealized positions (C—H = 0.95 Å) and refined as riding with Uiso(H) = 1.2 Ueq(C). The H atom bonded to N was freely refined.
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); 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 (Sheldrick, 1997).
Fig. 1. The molecular structure of (I) with displacement ellipsoids for the non-hydrogen atoms at the 50% probability level. |
C13H9ClN2O3 | F(000) = 2272 |
Mr = 276.67 | Dx = 1.483 Mg m−3 |
Orthorhombic, Fdd2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: F 2 -2d | Cell parameters from 9190 reflections |
a = 23.8527 (15) Å | θ = 2.8–25.2° |
b = 40.936 (3) Å | µ = 0.31 mm−1 |
c = 5.0780 (4) Å | T = 173 K |
V = 4958.3 (6) Å3 | Needle, colourless |
Z = 16 | 0.33 × 0.12 × 0.11 mm |
STOE IPDS II two-circle- diffractometer | 2181 independent reflections |
Radiation source: fine-focus sealed tube | 2083 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.071 |
ω scans | θmax = 25.0°, θmin = 2.6° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −26→28 |
Tmin = 0.904, Tmax = 0.956 | k = −40→48 |
10236 measured reflections | l = −6→6 |
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)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.090 | w = 1/[σ2(Fo2) + (0.0698P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
2181 reflections | Δρmax = 0.16 e Å−3 |
176 parameters | Δρmin = −0.23 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 955 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.00 (6) |
C13H9ClN2O3 | V = 4958.3 (6) Å3 |
Mr = 276.67 | Z = 16 |
Orthorhombic, Fdd2 | Mo Kα radiation |
a = 23.8527 (15) Å | µ = 0.31 mm−1 |
b = 40.936 (3) Å | T = 173 K |
c = 5.0780 (4) Å | 0.33 × 0.12 × 0.11 mm |
STOE IPDS II two-circle- diffractometer | 2181 independent reflections |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | 2083 reflections with I > 2σ(I) |
Tmin = 0.904, Tmax = 0.956 | Rint = 0.071 |
10236 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.090 | Δρmax = 0.16 e Å−3 |
S = 1.04 | Δρmin = −0.23 e Å−3 |
2181 reflections | Absolute structure: Flack (1983), 955 Friedel pairs |
176 parameters | Absolute structure parameter: 0.00 (6) |
1 restraint |
Experimental. ; |
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 | ||
Cl1 | 0.67478 (2) | 0.239794 (13) | 0.39083 (13) | 0.03892 (17) | |
C1 | 0.41096 (8) | 0.18013 (4) | 0.1564 (4) | 0.0221 (4) | |
O1 | 0.42715 (6) | 0.18287 (4) | −0.0713 (3) | 0.0355 (4) | |
N1 | 0.44331 (7) | 0.18661 (4) | 0.3687 (3) | 0.0215 (3) | |
H1 | 0.4295 (10) | 0.1826 (6) | 0.526 (6) | 0.026 (6)* | |
N2 | 0.35978 (7) | 0.12292 (4) | −0.0872 (4) | 0.0269 (4) | |
O2 | 0.40437 (7) | 0.11395 (4) | 0.0044 (4) | 0.0413 (4) | |
O3 | 0.34094 (7) | 0.11341 (5) | −0.2990 (4) | 0.0481 (5) | |
C11 | 0.35158 (8) | 0.17038 (5) | 0.2139 (3) | 0.0222 (4) | |
C12 | 0.32552 (8) | 0.14551 (5) | 0.0699 (4) | 0.0220 (4) | |
C13 | 0.26869 (9) | 0.13956 (5) | 0.0811 (4) | 0.0296 (5) | |
H13 | 0.2520 | 0.1232 | −0.0258 | 0.036* | |
C14 | 0.23644 (9) | 0.15811 (6) | 0.2528 (5) | 0.0360 (5) | |
H14 | 0.1973 | 0.1542 | 0.2658 | 0.043* | |
C15 | 0.26085 (9) | 0.18207 (6) | 0.4040 (6) | 0.0401 (5) | |
H15 | 0.2385 | 0.1944 | 0.5228 | 0.048* | |
C16 | 0.31833 (9) | 0.18851 (5) | 0.3848 (5) | 0.0320 (5) | |
H16 | 0.3347 | 0.2053 | 0.4886 | 0.038* | |
C21 | 0.49942 (7) | 0.19862 (4) | 0.3606 (4) | 0.0197 (4) | |
C22 | 0.53631 (8) | 0.18872 (5) | 0.5573 (4) | 0.0240 (4) | |
H22 | 0.5244 | 0.1735 | 0.6867 | 0.029* | |
C23 | 0.59041 (9) | 0.20106 (5) | 0.5651 (4) | 0.0267 (4) | |
H23 | 0.6157 | 0.1943 | 0.6990 | 0.032* | |
C24 | 0.60706 (8) | 0.22331 (4) | 0.3755 (4) | 0.0251 (4) | |
C25 | 0.57105 (8) | 0.23332 (5) | 0.1771 (4) | 0.0260 (4) | |
H25 | 0.5833 | 0.2485 | 0.0476 | 0.031* | |
C26 | 0.51674 (8) | 0.22091 (4) | 0.1699 (4) | 0.0230 (4) | |
H26 | 0.4916 | 0.2276 | 0.0354 | 0.028* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0231 (3) | 0.0424 (3) | 0.0512 (3) | −0.0075 (2) | −0.0017 (2) | 0.0032 (3) |
C1 | 0.0232 (9) | 0.0261 (9) | 0.0170 (9) | −0.0025 (7) | 0.0021 (8) | −0.0016 (8) |
O1 | 0.0297 (8) | 0.0608 (10) | 0.0161 (8) | −0.0190 (7) | 0.0022 (6) | −0.0030 (7) |
N1 | 0.0236 (8) | 0.0275 (8) | 0.0134 (8) | −0.0042 (6) | 0.0022 (7) | 0.0016 (7) |
N2 | 0.0248 (8) | 0.0264 (8) | 0.0296 (9) | −0.0019 (7) | −0.0011 (8) | −0.0049 (7) |
O2 | 0.0273 (9) | 0.0520 (10) | 0.0445 (10) | 0.0115 (7) | −0.0022 (7) | −0.0088 (8) |
O3 | 0.0438 (10) | 0.0580 (10) | 0.0424 (10) | −0.0010 (8) | −0.0110 (8) | −0.0273 (8) |
C11 | 0.0236 (10) | 0.0245 (9) | 0.0185 (10) | −0.0012 (7) | 0.0005 (7) | 0.0015 (7) |
C12 | 0.0230 (10) | 0.0232 (8) | 0.0198 (9) | 0.0006 (7) | 0.0011 (8) | 0.0013 (7) |
C13 | 0.0220 (10) | 0.0316 (10) | 0.0352 (12) | −0.0020 (7) | −0.0041 (9) | 0.0046 (9) |
C14 | 0.0201 (10) | 0.0446 (12) | 0.0432 (13) | 0.0004 (9) | 0.0032 (9) | 0.0062 (10) |
C15 | 0.0303 (11) | 0.0447 (12) | 0.0453 (14) | 0.0078 (10) | 0.0136 (11) | −0.0048 (11) |
C16 | 0.0320 (11) | 0.0348 (10) | 0.0294 (11) | −0.0002 (8) | 0.0055 (9) | −0.0071 (10) |
C21 | 0.0223 (9) | 0.0194 (8) | 0.0173 (8) | −0.0013 (7) | −0.0001 (7) | −0.0028 (7) |
C22 | 0.0270 (10) | 0.0256 (8) | 0.0196 (9) | 0.0012 (8) | 0.0014 (7) | 0.0030 (7) |
C23 | 0.0240 (10) | 0.0310 (10) | 0.0252 (10) | 0.0043 (8) | −0.0037 (8) | 0.0010 (8) |
C24 | 0.0205 (9) | 0.0251 (9) | 0.0298 (11) | −0.0016 (7) | 0.0029 (8) | −0.0055 (8) |
C25 | 0.0295 (10) | 0.0233 (8) | 0.0252 (11) | −0.0040 (7) | 0.0036 (8) | 0.0009 (8) |
C26 | 0.0272 (9) | 0.0233 (8) | 0.0185 (9) | −0.0026 (7) | −0.0001 (8) | −0.0001 (7) |
Cl1—C24 | 1.7522 (19) | C14—H14 | 0.9500 |
C1—O1 | 1.224 (3) | C15—C16 | 1.400 (3) |
C1—N1 | 1.352 (3) | C15—H15 | 0.9500 |
C1—C11 | 1.500 (3) | C16—H16 | 0.9500 |
N1—C21 | 1.426 (2) | C21—C22 | 1.392 (3) |
N1—H1 | 0.88 (3) | C21—C26 | 1.393 (3) |
N2—O2 | 1.218 (2) | C22—C23 | 1.386 (3) |
N2—O3 | 1.229 (3) | C22—H22 | 0.9500 |
N2—C12 | 1.469 (3) | C23—C24 | 1.384 (3) |
C11—C16 | 1.390 (3) | C23—H23 | 0.9500 |
C11—C12 | 1.399 (3) | C24—C25 | 1.386 (3) |
C12—C13 | 1.379 (3) | C25—C26 | 1.392 (3) |
C13—C14 | 1.389 (3) | C25—H25 | 0.9500 |
C13—H13 | 0.9500 | C26—H26 | 0.9500 |
C14—C15 | 1.375 (4) | ||
O1—C1—N1 | 123.72 (17) | C16—C15—H15 | 119.7 |
O1—C1—C11 | 120.40 (17) | C11—C16—C15 | 120.1 (2) |
N1—C1—C11 | 115.83 (17) | C11—C16—H16 | 119.9 |
C1—N1—C21 | 125.47 (16) | C15—C16—H16 | 119.9 |
C1—N1—H1 | 118.3 (16) | C22—C21—C26 | 120.14 (16) |
C21—N1—H1 | 116.2 (16) | C22—C21—N1 | 118.19 (16) |
O2—N2—O3 | 123.93 (19) | C26—C21—N1 | 121.59 (17) |
O2—N2—C12 | 117.93 (17) | C23—C22—C21 | 120.22 (17) |
O3—N2—C12 | 118.10 (17) | C23—C22—H22 | 119.9 |
C16—C11—C12 | 117.46 (18) | C21—C22—H22 | 119.9 |
C16—C11—C1 | 121.20 (18) | C24—C23—C22 | 119.14 (18) |
C12—C11—C1 | 120.75 (17) | C24—C23—H23 | 120.4 |
C13—C12—C11 | 122.96 (18) | C22—C23—H23 | 120.4 |
C13—C12—N2 | 117.26 (17) | C23—C24—C25 | 121.51 (17) |
C11—C12—N2 | 119.64 (16) | C23—C24—Cl1 | 119.15 (16) |
C12—C13—C14 | 118.3 (2) | C25—C24—Cl1 | 119.33 (15) |
C12—C13—H13 | 120.9 | C24—C25—C26 | 119.21 (18) |
C14—C13—H13 | 120.9 | C24—C25—H25 | 120.4 |
C15—C14—C13 | 120.4 (2) | C26—C25—H25 | 120.4 |
C15—C14—H14 | 119.8 | C25—C26—C21 | 119.78 (18) |
C13—C14—H14 | 119.8 | C25—C26—H26 | 120.1 |
C14—C15—C16 | 120.7 (2) | C21—C26—H26 | 120.1 |
C14—C15—H15 | 119.7 | ||
O1—C1—N1—C21 | 2.6 (3) | C13—C14—C15—C16 | 1.0 (4) |
C11—C1—N1—C21 | −175.00 (16) | C12—C11—C16—C15 | −1.3 (3) |
O1—C1—C11—C16 | −128.4 (2) | C1—C11—C16—C15 | 170.0 (2) |
N1—C1—C11—C16 | 49.3 (3) | C14—C15—C16—C11 | −0.8 (4) |
O1—C1—C11—C12 | 42.6 (3) | C1—N1—C21—C22 | −147.03 (19) |
N1—C1—C11—C12 | −139.74 (19) | C1—N1—C21—C26 | 36.1 (3) |
C16—C11—C12—C13 | 3.3 (3) | C26—C21—C22—C23 | 0.2 (3) |
C1—C11—C12—C13 | −168.00 (18) | N1—C21—C22—C23 | −176.74 (17) |
C16—C11—C12—N2 | −172.14 (18) | C21—C22—C23—C24 | 0.1 (3) |
C1—C11—C12—N2 | 16.5 (3) | C22—C23—C24—C25 | −0.5 (3) |
O2—N2—C12—C13 | −137.1 (2) | C22—C23—C24—Cl1 | 178.17 (15) |
O3—N2—C12—C13 | 40.6 (3) | C23—C24—C25—C26 | 0.6 (3) |
O2—N2—C12—C11 | 38.6 (3) | Cl1—C24—C25—C26 | −178.13 (14) |
O3—N2—C12—C11 | −143.7 (2) | C24—C25—C26—C21 | −0.2 (3) |
C11—C12—C13—C14 | −3.1 (3) | C22—C21—C26—C25 | −0.1 (3) |
N2—C12—C13—C14 | 172.42 (18) | N1—C21—C26—C25 | 176.67 (17) |
C12—C13—C14—C15 | 0.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.88 (3) | 2.05 (3) | 2.874 (2) | 157 (2) |
Symmetry code: (i) x, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | C13H9ClN2O3 |
Mr | 276.67 |
Crystal system, space group | Orthorhombic, Fdd2 |
Temperature (K) | 173 |
a, b, c (Å) | 23.8527 (15), 40.936 (3), 5.0780 (4) |
V (Å3) | 4958.3 (6) |
Z | 16 |
Radiation type | Mo Kα |
µ (mm−1) | 0.31 |
Crystal size (mm) | 0.33 × 0.12 × 0.11 |
Data collection | |
Diffractometer | STOE IPDS II two-circle- diffractometer |
Absorption correction | Multi-scan (MULABS; Spek, 2003; Blessing, 1995) |
Tmin, Tmax | 0.904, 0.956 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10236, 2181, 2083 |
Rint | 0.071 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.090, 1.04 |
No. of reflections | 2181 |
No. of parameters | 176 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.16, −0.23 |
Absolute structure | Flack (1983), 955 Friedel pairs |
Absolute structure parameter | 0.00 (6) |
Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.88 (3) | 2.05 (3) | 2.874 (2) | 157 (2) |
Symmetry code: (i) x, y, z+1. |
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
The benzanilide core is present in compounds with such a wide range of biological activities that it has been called a privileged structure (e.g. Makino et al., 2003; Igawa et al., 1999). As part of our studies in this area, the synthesis and structure of the title compound, (I), is now presented.
The geometric parameters for (I) are in the usual ranges. The dihedral angle between the two aromatic rings is 82.71 (6)°. The nitro group is twisted by 40.6 (2)° from the plane of the phenyl ring to which it is attached (Fig. 1). The crystal packing is stabilized by an N—H···O hydrogen bond (Table 1), leading to C(4) chains propagating in [001].