Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807030929/bt2410sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807030929/bt2410Isup2.hkl |
CCDC reference: 655064
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.022
- wR factor = 0.052
- Data-to-parameter ratio = 12.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H2B .. CL6 .. 2.85 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C6 H4 Cl3 N PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C6 H4 Cl3 N
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 26.37 From the CIF: _reflns_number_total 2640 Count of symmetry unique reflns 1737 Completeness (_total/calc) 151.99% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 903 Fraction of Friedel pairs measured 0.520 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 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 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 1 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Andrianov et al. (1971); Gowda et al. (2000, 2004, 2006); Gowda, Foro & Fuess (2007); Gowda, Paulus, Svoboda & Fuess (2007); Schlemper & Konnert (1967).
Single crystals of the title compound were obtained from a slow evaporation of an ethanolic solution of the analytical grade commercial sample.
The H atoms were located in difference map and their positions refined, with Uiso(H) = 1.2 Ueq (parent atom).
In the present work, the structure of trichloroaniline has been determined at 100 K, as part of our study of the effect of ring and side chain substitutions on the solid state structures of chemically and biologically important compounds (Gowda et al., 2000; Gowda et al., 2004; Gowda et al., 2006; Gowda, Foro, Fuess, 2007; Gowda, Paulus, Svoboda & Fuess, 2007). The cell pararameters of the title compound have already been determined (Schlemper & Konnert, 1967; Andrianov et al., 1971). There are two molecules in the asymmetric unit. The molecules are linked through N—H···N and N—H···Cl hydrogen bonds (Table 1 & Fig. 2).
For related literature, see: Andrianov et al. (1971); Gowda et al. (2000, 2004, 2006); Gowda, Foro & Fuess (2007); Gowda, Paulus, Svoboda & Fuess (2007); Schlemper & Konnert (1967).
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C6H4Cl3N | F(000) = 392 |
Mr = 196.45 | Dx = 1.778 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 2998 reflections |
a = 13.1933 (9) Å | θ = 2.8–26.5° |
b = 3.7913 (3) Å | µ = 1.16 mm−1 |
c = 15.774 (1) Å | T = 100 K |
β = 111.546 (8)° | Needle, colourless |
V = 733.88 (9) Å3 | 0.40 × 0.06 × 0.04 mm |
Z = 4 |
Oxford Diffraction Xcalibur single-crystal X-ray diffractometer with a Sapphire CCD detector | 2640 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2394 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
Detector resolution: 8.4012 pixels mm-1 | θmax = 26.4°, θmin = 2.5° |
Rotation method data acquisition using ω and φ scans | h = −16→16 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | k = −3→4 |
Tmin = 0.654, Tmax = 0.955 | l = −19→19 |
6014 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.022 | Only H-atom coordinates refined |
wR(F2) = 0.052 | w = 1/[σ2(Fo2) + (0.0308P)2 + 0.0195P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
2640 reflections | Δρmax = 0.31 e Å−3 |
205 parameters | Δρmin = −0.20 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 909 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.05 (6) |
C6H4Cl3N | V = 733.88 (9) Å3 |
Mr = 196.45 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 13.1933 (9) Å | µ = 1.16 mm−1 |
b = 3.7913 (3) Å | T = 100 K |
c = 15.774 (1) Å | 0.40 × 0.06 × 0.04 mm |
β = 111.546 (8)° |
Oxford Diffraction Xcalibur single-crystal X-ray diffractometer with a Sapphire CCD detector | 2640 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | 2394 reflections with I > 2σ(I) |
Tmin = 0.654, Tmax = 0.955 | Rint = 0.020 |
6014 measured reflections |
R[F2 > 2σ(F2)] = 0.022 | Only H-atom coordinates refined |
wR(F2) = 0.052 | Δρmax = 0.31 e Å−3 |
S = 1.06 | Δρmin = −0.20 e Å−3 |
2640 reflections | Absolute structure: Flack (1983), 909 Friedel pairs |
205 parameters | Absolute structure parameter: 0.05 (6) |
1 restraint |
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 | ||
C1 | −0.17763 (17) | 0.1364 (8) | −0.48017 (15) | 0.0136 (5) | |
C2 | −0.15064 (17) | 0.1814 (7) | −0.38618 (15) | 0.0136 (5) | |
C3 | −0.21934 (19) | 0.0893 (7) | −0.34146 (16) | 0.0161 (5) | |
H3 | −0.1964 (19) | 0.127 (8) | −0.2782 (16) | 0.019* | |
C4 | −0.32004 (18) | −0.0566 (7) | −0.39203 (16) | 0.0145 (5) | |
C5 | −0.35067 (17) | −0.1116 (8) | −0.48459 (15) | 0.0139 (5) | |
H5 | −0.4162 (19) | −0.201 (7) | −0.5161 (16) | 0.017* | |
C6 | −0.27979 (18) | −0.0155 (7) | −0.52667 (14) | 0.0145 (5) | |
C7 | 0.18568 (16) | −0.1233 (8) | −0.04221 (14) | 0.0123 (5) | |
C8 | 0.26254 (17) | −0.2849 (7) | −0.07128 (14) | 0.0137 (5) | |
C9 | 0.36317 (17) | −0.4004 (8) | −0.01229 (14) | 0.0130 (5) | |
H9 | 0.4118 (18) | −0.505 (7) | −0.0361 (15) | 0.016* | |
C10 | 0.38899 (16) | −0.3535 (7) | 0.08034 (14) | 0.0129 (5) | |
C11 | 0.31648 (17) | −0.1988 (7) | 0.11387 (15) | 0.0124 (5) | |
H11 | 0.3328 (18) | −0.175 (7) | 0.1782 (16) | 0.015* | |
C12 | 0.21624 (17) | −0.0889 (7) | 0.05230 (15) | 0.0127 (5) | |
N1 | −0.10582 (16) | 0.2177 (6) | −0.52298 (15) | 0.0183 (5) | |
H1A | −0.058 (2) | 0.357 (9) | −0.4968 (17) | 0.022* | |
H1B | −0.138 (2) | 0.262 (7) | −0.5786 (17) | 0.022* | |
N2 | 0.08434 (16) | −0.0177 (6) | −0.10248 (14) | 0.0167 (5) | |
H2A | 0.077 (2) | 0.014 (8) | −0.1578 (18) | 0.020* | |
H2B | 0.0519 (19) | 0.132 (8) | −0.0836 (16) | 0.020* | |
Cl1 | −0.02316 (4) | 0.36022 (18) | −0.32306 (4) | 0.01969 (14) | |
Cl2 | −0.40873 (4) | −0.17199 (18) | −0.33787 (4) | 0.01946 (15) | |
Cl3 | −0.31863 (5) | −0.09196 (19) | −0.64317 (4) | 0.02145 (16) | |
Cl4 | 0.22936 (4) | −0.34462 (19) | −0.18807 (3) | 0.01808 (15) | |
Cl5 | 0.51505 (4) | −0.49705 (17) | 0.15626 (4) | 0.01731 (15) | |
Cl6 | 0.12272 (4) | 0.09515 (17) | 0.09410 (4) | 0.01712 (15) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0135 (10) | 0.0103 (14) | 0.0163 (11) | 0.0037 (11) | 0.0047 (9) | 0.0008 (10) |
C2 | 0.0108 (10) | 0.0084 (14) | 0.0167 (11) | −0.0006 (11) | −0.0007 (9) | 0.0011 (10) |
C3 | 0.0191 (11) | 0.0136 (15) | 0.0128 (11) | 0.0024 (11) | 0.0027 (9) | 0.0003 (11) |
C4 | 0.0155 (11) | 0.0084 (15) | 0.0228 (12) | 0.0008 (11) | 0.0105 (10) | 0.0019 (10) |
C5 | 0.0109 (10) | 0.0118 (15) | 0.0165 (11) | −0.0002 (12) | 0.0020 (9) | 0.0004 (11) |
C6 | 0.0173 (11) | 0.0131 (15) | 0.0100 (10) | 0.0032 (11) | 0.0014 (9) | −0.0015 (10) |
C7 | 0.0127 (10) | 0.0080 (13) | 0.0165 (11) | −0.0026 (11) | 0.0059 (9) | 0.0025 (10) |
C8 | 0.0162 (11) | 0.0142 (15) | 0.0117 (10) | −0.0056 (11) | 0.0061 (9) | −0.0018 (10) |
C9 | 0.0132 (10) | 0.0106 (14) | 0.0178 (11) | −0.0026 (11) | 0.0087 (9) | −0.0017 (10) |
C10 | 0.0091 (10) | 0.0115 (14) | 0.0162 (11) | 0.0002 (11) | 0.0024 (9) | 0.0027 (11) |
C11 | 0.0144 (11) | 0.0091 (15) | 0.0132 (11) | −0.0030 (10) | 0.0047 (9) | −0.0001 (10) |
C12 | 0.0135 (10) | 0.0093 (15) | 0.0194 (11) | −0.0017 (11) | 0.0109 (9) | −0.0009 (10) |
N1 | 0.0165 (10) | 0.0214 (15) | 0.0166 (10) | −0.0027 (10) | 0.0056 (9) | −0.0021 (10) |
N2 | 0.0134 (10) | 0.0205 (14) | 0.0165 (10) | 0.0031 (10) | 0.0060 (8) | 0.0023 (10) |
Cl1 | 0.0148 (3) | 0.0204 (4) | 0.0189 (3) | −0.0034 (3) | 0.0004 (2) | 0.0003 (3) |
Cl2 | 0.0201 (3) | 0.0214 (4) | 0.0196 (3) | −0.0022 (3) | 0.0105 (2) | 0.0010 (3) |
Cl3 | 0.0260 (3) | 0.0255 (4) | 0.0116 (3) | −0.0037 (3) | 0.0056 (2) | −0.0032 (3) |
Cl4 | 0.0162 (3) | 0.0254 (4) | 0.0120 (3) | −0.0030 (3) | 0.0044 (2) | −0.0027 (3) |
Cl5 | 0.0130 (3) | 0.0201 (4) | 0.0163 (3) | 0.0027 (3) | 0.0025 (2) | 0.0003 (2) |
Cl6 | 0.0166 (3) | 0.0168 (4) | 0.0220 (3) | 0.0013 (3) | 0.0119 (2) | −0.0020 (3) |
C1—N1 | 1.385 (3) | C7—C12 | 1.400 (3) |
C1—C6 | 1.400 (3) | C8—C9 | 1.383 (3) |
C1—C2 | 1.402 (3) | C8—Cl4 | 1.745 (2) |
C2—C3 | 1.382 (3) | C9—C10 | 1.385 (3) |
C2—Cl1 | 1.746 (2) | C9—H9 | 0.94 (2) |
C3—C4 | 1.389 (3) | C10—C11 | 1.382 (3) |
C3—H3 | 0.94 (2) | C10—Cl5 | 1.742 (2) |
C4—C5 | 1.380 (3) | C11—C12 | 1.386 (3) |
C4—Cl2 | 1.739 (2) | C11—H11 | 0.96 (2) |
C5—C6 | 1.380 (3) | C12—Cl6 | 1.744 (2) |
C5—H5 | 0.89 (2) | N1—H1A | 0.81 (3) |
C6—Cl3 | 1.741 (2) | N1—H1B | 0.84 (2) |
C7—N2 | 1.385 (3) | N2—H2A | 0.85 (3) |
C7—C8 | 1.398 (3) | N2—H2B | 0.83 (3) |
N1—C1—C6 | 122.4 (2) | C9—C8—C7 | 123.41 (19) |
N1—C1—C2 | 122.3 (2) | C9—C8—Cl4 | 118.41 (17) |
C6—C1—C2 | 115.2 (2) | C7—C8—Cl4 | 118.17 (16) |
C3—C2—C1 | 123.3 (2) | C8—C9—C10 | 118.2 (2) |
C3—C2—Cl1 | 118.81 (17) | C8—C9—H9 | 119.4 (14) |
C1—C2—Cl1 | 117.87 (18) | C10—C9—H9 | 122.4 (14) |
C2—C3—C4 | 118.4 (2) | C11—C10—C9 | 121.4 (2) |
C2—C3—H3 | 119.1 (15) | C11—C10—Cl5 | 119.34 (16) |
C4—C3—H3 | 122.4 (15) | C9—C10—Cl5 | 119.23 (17) |
C5—C4—C3 | 121.0 (2) | C10—C11—C12 | 118.41 (19) |
C5—C4—Cl2 | 119.55 (18) | C10—C11—H11 | 121.7 (14) |
C3—C4—Cl2 | 119.49 (17) | C12—C11—H11 | 119.8 (14) |
C6—C5—C4 | 118.8 (2) | C11—C12—C7 | 123.1 (2) |
C6—C5—H5 | 121.5 (15) | C11—C12—Cl6 | 118.73 (17) |
C4—C5—H5 | 119.6 (15) | C7—C12—Cl6 | 118.21 (16) |
C5—C6—C1 | 123.3 (2) | C1—N1—H1A | 116.0 (18) |
C5—C6—Cl3 | 118.36 (17) | C1—N1—H1B | 112.1 (17) |
C1—C6—Cl3 | 118.35 (17) | H1A—N1—H1B | 114 (3) |
N2—C7—C8 | 122.3 (2) | C7—N2—H2A | 117.7 (17) |
N2—C7—C12 | 122.1 (2) | C7—N2—H2B | 116.6 (17) |
C8—C7—C12 | 115.46 (19) | H2A—N2—H2B | 113 (3) |
N1—C1—C2—C3 | −177.4 (3) | N2—C7—C8—C9 | −178.4 (3) |
C6—C1—C2—C3 | −0.9 (4) | C12—C7—C8—C9 | −1.0 (4) |
N1—C1—C2—Cl1 | 2.1 (4) | N2—C7—C8—Cl4 | 1.5 (4) |
C6—C1—C2—Cl1 | 178.57 (19) | C12—C7—C8—Cl4 | 178.84 (19) |
C1—C2—C3—C4 | 0.3 (4) | C7—C8—C9—C10 | 0.0 (4) |
Cl1—C2—C3—C4 | −179.3 (2) | Cl4—C8—C9—C10 | −179.8 (2) |
C2—C3—C4—C5 | 0.6 (4) | C8—C9—C10—C11 | 0.6 (4) |
C2—C3—C4—Cl2 | −179.5 (2) | C8—C9—C10—Cl5 | 179.9 (2) |
C3—C4—C5—C6 | −0.7 (4) | C9—C10—C11—C12 | −0.2 (4) |
Cl2—C4—C5—C6 | 179.4 (2) | Cl5—C10—C11—C12 | −179.51 (19) |
C4—C5—C6—C1 | −0.1 (4) | C10—C11—C12—C7 | −0.8 (4) |
C4—C5—C6—Cl3 | 179.1 (2) | C10—C11—C12—Cl6 | 178.2 (2) |
N1—C1—C6—C5 | 177.3 (3) | N2—C7—C12—C11 | 178.8 (2) |
C2—C1—C6—C5 | 0.8 (4) | C8—C7—C12—C11 | 1.4 (4) |
N1—C1—C6—Cl3 | −1.9 (4) | N2—C7—C12—Cl6 | −0.3 (4) |
C2—C1—C6—Cl3 | −178.4 (2) | C8—C7—C12—Cl6 | −177.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···N1i | 0.81 (3) | 2.48 (3) | 3.229 (3) | 155 (2) |
N1—H1A···Cl1 | 0.81 (3) | 2.61 (3) | 2.983 (2) | 110 (2) |
N1—H1B···Cl3 | 0.84 (3) | 2.60 (3) | 2.991 (2) | 110 (2) |
N2—H2A···Cl1 | 0.85 (3) | 2.78 (3) | 3.542 (2) | 150 (2) |
N2—H2B···Cl6ii | 0.83 (3) | 2.85 (3) | 3.626 (2) | 156 (2) |
Symmetry codes: (i) −x, y+1/2, −z−1; (ii) −x, y+1/2, −z. |
Experimental details
Crystal data | |
Chemical formula | C6H4Cl3N |
Mr | 196.45 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 100 |
a, b, c (Å) | 13.1933 (9), 3.7913 (3), 15.774 (1) |
β (°) | 111.546 (8) |
V (Å3) | 733.88 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.16 |
Crystal size (mm) | 0.40 × 0.06 × 0.04 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur single-crystal X-ray diffractometer with a Sapphire CCD detector |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2006) |
Tmin, Tmax | 0.654, 0.955 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6014, 2640, 2394 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.022, 0.052, 1.06 |
No. of reflections | 2640 |
No. of parameters | 205 |
No. of restraints | 1 |
H-atom treatment | Only H-atom coordinates refined |
Δρmax, Δρmin (e Å−3) | 0.31, −0.20 |
Absolute structure | Flack (1983), 909 Friedel pairs |
Absolute structure parameter | 0.05 (6) |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), CrysAlis RED, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···N1i | 0.81 (3) | 2.48 (3) | 3.229 (3) | 155 (2) |
N1—H1A···Cl1 | 0.81 (3) | 2.61 (3) | 2.983 (2) | 110 (2) |
N1—H1B···Cl3 | 0.84 (3) | 2.60 (3) | 2.991 (2) | 110 (2) |
N2—H2A···Cl1 | 0.85 (3) | 2.78 (3) | 3.542 (2) | 150 (2) |
N2—H2B···Cl6ii | 0.83 (3) | 2.85 (3) | 3.626 (2) | 156 (2) |
Symmetry codes: (i) −x, y+1/2, −z−1; (ii) −x, y+1/2, −z. |
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In the present work, the structure of trichloroaniline has been determined at 100 K, as part of our study of the effect of ring and side chain substitutions on the solid state structures of chemically and biologically important compounds (Gowda et al., 2000; Gowda et al., 2004; Gowda et al., 2006; Gowda, Foro, Fuess, 2007; Gowda, Paulus, Svoboda & Fuess, 2007). The cell pararameters of the title compound have already been determined (Schlemper & Konnert, 1967; Andrianov et al., 1971). There are two molecules in the asymmetric unit. The molecules are linked through N—H···N and N—H···Cl hydrogen bonds (Table 1 & Fig. 2).