Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805016557/rz6078sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805016557/rz6078Isup2.hkl |
CCDC reference: 274620
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.004 Å
- R factor = 0.043
- wR factor = 0.100
- Data-to-parameter ratio = 16.9
checkCIF/PLATON results
No syntax errors found
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 27.50 From the CIF: _reflns_number_total 1928 Count of symmetry unique reflns 1191 Completeness (_total/calc) 161.88% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 737 Fraction of Friedel pairs measured 0.619 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C7H5Cl2NO2 | F(000) = 416 |
Mr = 206.02 | Dx = 1.625 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1332 reflections |
a = 4.9893 (8) Å | θ = 3.0–21.4° |
b = 6.3013 (10) Å | µ = 0.72 mm−1 |
c = 26.790 (4) Å | T = 292 K |
V = 842.2 (2) Å3 | Plate, colorless |
Z = 4 | 0.40 × 0.20 × 0.08 mm |
Bruker SMART CCD area-detector diffractometer | 1928 independent reflections |
Radiation source: fine-focus sealed tube | 1607 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
φ and ω scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −6→6 |
Tmin = 0.761, Tmax = 0.944 | k = −8→6 |
5081 measured reflections | l = −33→34 |
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)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.100 | w = 1/[σ2(Fo2) + (0.0483P)2 + 0.0861P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
1928 reflections | Δρmax = 0.29 e Å−3 |
114 parameters | Δρmin = −0.22 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 741 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.01 (10) |
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 | 0.7674 (5) | 0.7780 (4) | 0.09519 (9) | 0.0367 (6) | |
C2 | 0.8967 (5) | 0.7890 (4) | 0.14153 (9) | 0.0399 (6) | |
C3 | 0.8407 (6) | 0.6472 (5) | 0.17903 (10) | 0.0457 (7) | |
H3 | 0.9275 | 0.6570 | 0.2097 | 0.055* | |
C4 | 0.6544 (6) | 0.4904 (4) | 0.17063 (9) | 0.0458 (7) | |
C5 | 0.5244 (6) | 0.4722 (5) | 0.12565 (10) | 0.0531 (8) | |
H5 | 0.4001 | 0.3646 | 0.1203 | 0.064* | |
C6 | 0.5825 (6) | 0.6175 (5) | 0.08838 (10) | 0.0478 (7) | |
H6 | 0.4944 | 0.6066 | 0.0579 | 0.057* | |
C7 | 0.8232 (5) | 0.9288 (4) | 0.05337 (9) | 0.0367 (6) | |
Cl1 | 1.12555 (18) | 0.98806 (14) | 0.15413 (3) | 0.0667 (3) | |
Cl2 | 0.5816 (2) | 0.31197 (15) | 0.21809 (3) | 0.0750 (3) | |
N1 | 0.6057 (4) | 1.0107 (4) | 0.03270 (8) | 0.0418 (5) | |
O2 | 0.6347 (4) | 1.1148 (3) | −0.01257 (7) | 0.0514 (5) | |
H2 | 0.5797 | 1.2369 | −0.0099 | 0.077* | |
O1 | 1.0503 (3) | 0.9707 (3) | 0.03846 (7) | 0.0492 (5) | |
H1 | 0.446 (5) | 0.974 (4) | 0.0409 (8) | 0.033 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0273 (13) | 0.0379 (14) | 0.0449 (14) | −0.0030 (11) | 0.0030 (11) | 0.0010 (12) |
C2 | 0.0314 (14) | 0.0378 (14) | 0.0504 (14) | −0.0079 (11) | −0.0016 (12) | −0.0047 (12) |
C3 | 0.0441 (16) | 0.0532 (16) | 0.0398 (13) | −0.0071 (13) | −0.0041 (12) | −0.0001 (13) |
C4 | 0.0558 (17) | 0.0426 (14) | 0.0390 (13) | −0.0111 (14) | 0.0047 (12) | 0.0039 (12) |
C5 | 0.0619 (19) | 0.0480 (18) | 0.0494 (15) | −0.0247 (16) | −0.0008 (14) | 0.0022 (13) |
C6 | 0.0492 (17) | 0.0530 (17) | 0.0412 (14) | −0.0166 (15) | −0.0070 (13) | 0.0015 (13) |
C7 | 0.0254 (13) | 0.0390 (13) | 0.0457 (14) | 0.0002 (10) | 0.0018 (10) | 0.0032 (11) |
Cl1 | 0.0664 (5) | 0.0680 (5) | 0.0658 (5) | −0.0366 (5) | −0.0135 (4) | 0.0018 (4) |
Cl2 | 0.1028 (7) | 0.0697 (6) | 0.0526 (4) | −0.0325 (5) | 0.0003 (5) | 0.0203 (4) |
N1 | 0.0237 (11) | 0.0501 (13) | 0.0514 (12) | 0.0005 (11) | 0.0041 (10) | 0.0142 (12) |
O2 | 0.0425 (12) | 0.0518 (11) | 0.0598 (11) | 0.0109 (10) | 0.0058 (10) | 0.0196 (10) |
O1 | 0.0236 (9) | 0.0610 (12) | 0.0629 (12) | −0.0018 (9) | 0.0048 (8) | 0.0232 (11) |
C1—C6 | 1.381 (4) | C5—C6 | 1.385 (4) |
C1—C2 | 1.401 (3) | C5—H5 | 0.9300 |
C1—C7 | 1.495 (3) | C6—H6 | 0.9300 |
C2—C3 | 1.374 (4) | C7—O1 | 1.230 (3) |
C2—Cl1 | 1.729 (3) | C7—N1 | 1.323 (3) |
C3—C4 | 1.375 (4) | N1—O2 | 1.386 (3) |
C3—H3 | 0.9300 | N1—H1 | 0.86 (3) |
C4—C5 | 1.373 (4) | O2—H2 | 0.8200 |
C4—Cl2 | 1.736 (3) | ||
C6—C1—C2 | 117.4 (2) | C4—C5—H5 | 120.7 |
C6—C1—C7 | 119.4 (2) | C6—C5—H5 | 120.7 |
C2—C1—C7 | 123.1 (2) | C1—C6—C5 | 121.9 (2) |
C3—C2—C1 | 121.5 (2) | C1—C6—H6 | 119.0 |
C3—C2—Cl1 | 117.63 (19) | C5—C6—H6 | 119.0 |
C1—C2—Cl1 | 120.9 (2) | O1—C7—N1 | 122.4 (2) |
C2—C3—C4 | 119.1 (2) | O1—C7—C1 | 123.5 (2) |
C2—C3—H3 | 120.5 | N1—C7—C1 | 114.1 (2) |
C4—C3—H3 | 120.5 | C7—N1—O2 | 117.7 (2) |
C5—C4—C3 | 121.5 (2) | C7—N1—H1 | 123.3 (16) |
C5—C4—Cl2 | 119.3 (2) | O2—N1—H1 | 116.6 (16) |
C3—C4—Cl2 | 119.1 (2) | N1—O2—H2 | 109.5 |
C4—C5—C6 | 118.6 (3) | ||
C6—C1—C2—C3 | −0.6 (4) | C2—C1—C6—C5 | 0.2 (4) |
C7—C1—C2—C3 | −179.8 (3) | C7—C1—C6—C5 | 179.4 (3) |
C6—C1—C2—Cl1 | −178.5 (2) | C4—C5—C6—C1 | 0.4 (5) |
C7—C1—C2—Cl1 | 2.3 (4) | C6—C1—C7—O1 | −129.2 (3) |
C1—C2—C3—C4 | 0.4 (4) | C2—C1—C7—O1 | 50.1 (4) |
Cl1—C2—C3—C4 | 178.3 (2) | C6—C1—C7—N1 | 49.3 (4) |
C2—C3—C4—C5 | 0.3 (4) | C2—C1—C7—N1 | −131.4 (3) |
C2—C3—C4—Cl2 | −179.6 (2) | O1—C7—N1—O2 | 12.1 (4) |
C3—C4—C5—C6 | −0.6 (5) | C1—C7—N1—O2 | −166.5 (2) |
Cl2—C4—C5—C6 | 179.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O2i | 0.82 | 2.48 | 3.095 (3) | 132 |
O2—H2···O1i | 0.82 | 2.00 | 2.735 (3) | 149 |
N1—H1···O1ii | 0.86 (3) | 1.98 (3) | 2.787 (3) | 157 (2) |
C6—H6···O2iii | 0.93 | 2.58 | 3.355 (3) | 142 |
Symmetry codes: (i) x−1/2, −y+5/2, −z; (ii) x−1, y, z; (iii) x−1/2, −y+3/2, −z. |
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