organic compounds
1-Chloro-3,4-dinitrobenzene–1,4-dioxane (1/1)
aDepartment of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ, England
*Correspondence e-mail: sarah.barnett@ucl.ac.uk
The solvate structure of 1-chloro-3,4-dinitrobenzene with 1,4-dioxane, C6H3ClN2O4·C4H8N2, is reported. Alternating molecules of 3,4-dinitro-1-chlorobenzene and 1,4-dioxane are linked by C—H⋯O hydrogen bonds into a continuous two-dimensional sheet.
Comment
The title compound, (I), was produced during an experimental crystallization polymorph screen on 1-chloro-3,4-dinitrobenzene (3,4-DNCB). Compound (I) crystallizes in the P with one molecule of 3,4-DNCB and one molecule of 1,4-dioxane in the (Fig. 1).
The is characterized by alternating molecules of 3,4-DNCB and 1,4-dioxane, linked by a series of C—H⋯O hydrogen bonds (Table 1) into a continuous two-dimensional sheet which lies parallel to the (11) plane (Fig. 2). Alternating 3,4-DNCB molecules and 1,4-dioxane are linked by pairwise C—H⋯O hydrogen bonds, forming a chain which runs parallel to the body diagonal (111). These chains are then hydrogen-bonded together, forming a sheet via two C—H⋯O interactions between two 3,4-DNCB molecules and one C—H⋯O interaction between the 3,4-DNCB molecule and a 1,4-dioxane molecule of the adjacent chain. Viewing the down the a axis reveals that there are alternating layers of 3,4-DNCB and 1,4-dioxane (Fig. 3).
of (I)Experimental
The title compound was recrystallized from 1,4-dioxane solution by slow evaporation at 298 K.
Crystal data
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Refinement
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H atoms were located in a difference Fourier map and refined freely [C—H = 0.938 (15)–0.996 (19) Å]. The three reflections with the greatest discrepancies were omitted from the refinement.
Data collection: SMART (Bruker, 2001); cell SAINT (Bruker, 2001); 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, 2000) and MERCURY (Bruno et al., 2002); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
Supporting information
https://doi.org/10.1107/S1600536806011226/wn2016sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536806011226/wn2016Isup2.hkl
Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); 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, 2000) and OLEX (Dolomanov et al., 2003); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).C6H3ClN2O4·C4H8O2 | Z = 2 |
Mr = 290.66 | F(000) = 300 |
Triclinic, P1 | Dx = 1.616 Mg m−3 |
a = 8.2976 (12) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.7112 (13) Å | Cell parameters from 3669 reflections |
c = 8.8015 (13) Å | θ = 2.5–28.2° |
α = 103.661 (2)° | µ = 0.35 mm−1 |
β = 103.909 (2)° | T = 150 K |
γ = 91.718 (2)° | Block, yellow |
V = 597.52 (15) Å3 | 0.86 × 0.67 × 0.45 mm |
Bruker SMART APEX diffractometer | 2650 independent reflections |
Radiation source: fine-focus sealed tube | 2529 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
Narrow–frame ω scans | θmax = 28.2°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −10→10 |
Tmin = 0.738, Tmax = 0.856 | k = −11→11 |
4424 measured reflections | l = −11→11 |
Refinement on F2 | Primary atom site location: Direct methods |
Least-squares matrix: full | Secondary atom site location: Difference Fourier synthesis |
R[F2 > 2σ(F2)] = 0.031 | Hydrogen site location: Found from delta-F |
wR(F2) = 0.084 | All H-atom parameters refined |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0478P)2 + 0.1587P] where P = (Fo2 + 2Fc2)/3 |
2647 reflections | (Δ/σ)max < 0.001 |
216 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
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 | 0.01692 (14) | 0.14991 (13) | 0.38735 (13) | 0.0189 (2) | |
C2 | 0.13820 (13) | 0.25986 (13) | 0.49998 (13) | 0.0182 (2) | |
C3 | 0.09882 (14) | 0.37166 (13) | 0.62157 (13) | 0.0198 (2) | |
H3 | 0.1791 (19) | 0.4482 (18) | 0.6968 (18) | 0.024 (4)* | |
C4 | −0.06714 (14) | 0.36928 (13) | 0.62793 (13) | 0.0205 (2) | |
C5 | −0.18948 (14) | 0.25951 (15) | 0.51873 (14) | 0.0233 (2) | |
H5 | −0.304 (2) | 0.262 (2) | 0.526 (2) | 0.035 (4)* | |
C6 | −0.14693 (14) | 0.14773 (14) | 0.39675 (14) | 0.0218 (2) | |
H6 | −0.2275 (19) | 0.0712 (18) | 0.3186 (18) | 0.022 (3)* | |
Cl1 | −0.11770 (4) | 0.50731 (4) | 0.78178 (4) | 0.02978 (11) | |
N1 | 0.05511 (12) | 0.04236 (11) | 0.24729 (11) | 0.0204 (2) | |
O1 | −0.00297 (12) | −0.09537 (10) | 0.21122 (11) | 0.0300 (2) | |
O2 | 0.13920 (12) | 0.09876 (11) | 0.17386 (10) | 0.0295 (2) | |
N2 | 0.31546 (12) | 0.25335 (12) | 0.50183 (11) | 0.0217 (2) | |
O3 | 0.36588 (11) | 0.12279 (11) | 0.46586 (11) | 0.0301 (2) | |
O4 | 0.40217 (11) | 0.37924 (11) | 0.54379 (12) | 0.0318 (2) | |
C7 | 0.50812 (15) | 0.71687 (15) | 0.86037 (14) | 0.0265 (3) | |
H7A | 0.512 (2) | 0.821 (2) | 0.8349 (19) | 0.034 (4)* | |
H7B | 0.533 (2) | 0.635 (2) | 0.772 (2) | 0.036 (4)* | |
C8 | 0.62967 (15) | 0.72245 (16) | 1.01944 (15) | 0.0264 (3) | |
H8A | 0.6304 (19) | 0.6196 (19) | 1.0408 (18) | 0.026 (4)* | |
H8B | 0.746 (2) | 0.756 (2) | 1.020 (2) | 0.040 (4)* | |
C9 | 0.42101 (16) | 0.79512 (16) | 1.15303 (14) | 0.0273 (3) | |
H9A | 0.414 (2) | 0.695 (2) | 1.1806 (18) | 0.029 (4)* | |
H9B | 0.398 (2) | 0.875 (2) | 1.237 (2) | 0.039 (4)* | |
C10 | 0.29983 (16) | 0.78846 (16) | 0.99319 (15) | 0.0272 (3) | |
H10A | 0.297 (2) | 0.891 (2) | 0.970 (2) | 0.037 (4)* | |
H10B | 0.186 (2) | 0.757 (2) | 0.991 (2) | 0.035 (4)* | |
O5 | 0.34241 (11) | 0.67501 (10) | 0.86581 (10) | 0.0258 (2) | |
O6 | 0.58807 (11) | 0.83433 (11) | 1.14873 (10) | 0.0273 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0205 (5) | 0.0180 (5) | 0.0177 (5) | 0.0016 (4) | 0.0039 (4) | 0.0044 (4) |
C2 | 0.0155 (5) | 0.0194 (5) | 0.0203 (5) | 0.0011 (4) | 0.0046 (4) | 0.0058 (4) |
C3 | 0.0193 (5) | 0.0190 (5) | 0.0204 (5) | 0.0002 (4) | 0.0045 (4) | 0.0046 (4) |
C4 | 0.0223 (5) | 0.0211 (5) | 0.0207 (5) | 0.0051 (4) | 0.0083 (4) | 0.0068 (4) |
C5 | 0.0170 (5) | 0.0298 (6) | 0.0248 (5) | 0.0025 (4) | 0.0055 (4) | 0.0099 (5) |
C6 | 0.0179 (5) | 0.0246 (6) | 0.0211 (5) | −0.0012 (4) | 0.0014 (4) | 0.0067 (4) |
Cl1 | 0.02999 (17) | 0.03041 (18) | 0.02956 (17) | 0.00620 (12) | 0.01481 (12) | 0.00096 (12) |
N1 | 0.0198 (4) | 0.0199 (5) | 0.0190 (4) | 0.0023 (3) | 0.0018 (3) | 0.0031 (4) |
O1 | 0.0339 (5) | 0.0195 (4) | 0.0312 (4) | −0.0023 (3) | 0.0049 (4) | 0.0000 (3) |
O2 | 0.0367 (5) | 0.0284 (5) | 0.0260 (4) | 0.0016 (4) | 0.0151 (4) | 0.0047 (3) |
N2 | 0.0168 (4) | 0.0261 (5) | 0.0198 (4) | 0.0005 (4) | 0.0047 (3) | 0.0017 (4) |
O3 | 0.0229 (4) | 0.0300 (5) | 0.0334 (5) | 0.0083 (3) | 0.0067 (4) | 0.0005 (4) |
O4 | 0.0217 (4) | 0.0307 (5) | 0.0390 (5) | −0.0074 (4) | 0.0089 (4) | 0.0010 (4) |
C7 | 0.0261 (6) | 0.0276 (6) | 0.0228 (5) | −0.0011 (5) | 0.0077 (5) | −0.0002 (5) |
C8 | 0.0224 (6) | 0.0268 (6) | 0.0258 (6) | 0.0001 (5) | 0.0058 (4) | −0.0009 (5) |
C9 | 0.0252 (6) | 0.0327 (7) | 0.0218 (5) | −0.0001 (5) | 0.0070 (5) | 0.0017 (5) |
C10 | 0.0240 (6) | 0.0301 (6) | 0.0242 (6) | 0.0034 (5) | 0.0061 (5) | 0.0002 (5) |
O5 | 0.0224 (4) | 0.0267 (4) | 0.0223 (4) | −0.0012 (3) | 0.0034 (3) | −0.0027 (3) |
O6 | 0.0239 (4) | 0.0292 (5) | 0.0225 (4) | −0.0033 (3) | 0.0045 (3) | −0.0036 (3) |
C1—C6 | 1.3816 (16) | N2—O3 | 1.2210 (14) |
C1—C2 | 1.3881 (15) | C7—O5 | 1.4267 (14) |
C1—N1 | 1.4691 (14) | C7—C8 | 1.5052 (18) |
C2—C3 | 1.3768 (15) | C7—H7A | 0.982 (17) |
C2—N2 | 1.4700 (14) | C7—H7B | 0.990 (17) |
C3—C4 | 1.3913 (15) | C8—O6 | 1.4314 (14) |
C3—H3 | 0.938 (15) | C8—H8A | 0.958 (16) |
C4—C5 | 1.3811 (16) | C8—H8B | 0.996 (19) |
C4—Cl1 | 1.7291 (11) | C9—O6 | 1.4292 (15) |
C5—C6 | 1.3908 (17) | C9—C10 | 1.5071 (17) |
C5—H5 | 0.969 (17) | C9—H9A | 0.962 (17) |
C6—H6 | 0.949 (15) | C9—H9B | 0.951 (18) |
N1—O1 | 1.2184 (13) | C10—O5 | 1.4306 (14) |
N1—O2 | 1.2215 (13) | C10—H10A | 0.964 (18) |
N2—O4 | 1.2208 (13) | C10—H10B | 0.973 (17) |
C6—C1—C2 | 120.56 (10) | O5—C7—H7A | 108.9 (10) |
C6—C1—N1 | 117.89 (10) | C8—C7—H7A | 110.4 (10) |
C2—C1—N1 | 121.33 (10) | O5—C7—H7B | 107.0 (10) |
C3—C2—C1 | 121.33 (10) | C8—C7—H7B | 110.9 (10) |
C3—C2—N2 | 117.30 (9) | H7A—C7—H7B | 109.0 (13) |
C1—C2—N2 | 121.19 (10) | O6—C8—C7 | 110.89 (10) |
C2—C3—C4 | 117.37 (10) | O6—C8—H8A | 109.6 (9) |
C2—C3—H3 | 122.1 (9) | C7—C8—H8A | 110.3 (9) |
C4—C3—H3 | 120.5 (9) | O6—C8—H8B | 106.8 (10) |
C5—C4—C3 | 122.32 (10) | C7—C8—H8B | 111.9 (10) |
C5—C4—Cl1 | 119.85 (9) | H8A—C8—H8B | 107.3 (14) |
C3—C4—Cl1 | 117.82 (9) | O6—C9—C10 | 111.09 (10) |
C4—C5—C6 | 119.34 (10) | O6—C9—H9A | 109.7 (10) |
C4—C5—H5 | 120.1 (10) | C10—C9—H9A | 110.3 (9) |
C6—C5—H5 | 120.6 (10) | O6—C9—H9B | 106.5 (11) |
C1—C6—C5 | 119.06 (10) | C10—C9—H9B | 110.7 (11) |
C1—C6—H6 | 119.0 (9) | H9A—C9—H9B | 108.3 (14) |
C5—C6—H6 | 121.9 (9) | O5—C10—C9 | 110.50 (10) |
O1—N1—O2 | 125.13 (10) | O5—C10—H10A | 110.2 (10) |
O1—N1—C1 | 117.35 (9) | C9—C10—H10A | 110.8 (11) |
O2—N1—C1 | 117.50 (9) | O5—C10—H10B | 106.6 (10) |
O4—N2—O3 | 124.94 (10) | C9—C10—H10B | 113.0 (10) |
O4—N2—C2 | 117.27 (10) | H10A—C10—H10B | 105.5 (14) |
O3—N2—C2 | 117.76 (9) | C7—O5—C10 | 109.34 (9) |
O5—C7—C8 | 110.53 (10) | C9—O6—C8 | 109.74 (9) |
C6—C1—C2—C3 | −1.45 (17) | C2—C1—N1—O1 | 137.79 (11) |
N1—C1—C2—C3 | 173.08 (10) | C6—C1—N1—O2 | 130.77 (11) |
C6—C1—C2—N2 | 173.60 (10) | C2—C1—N1—O2 | −43.91 (15) |
N1—C1—C2—N2 | −11.86 (16) | C3—C2—N2—O4 | −37.51 (14) |
C1—C2—C3—C4 | 0.51 (17) | C1—C2—N2—O4 | 147.24 (11) |
N2—C2—C3—C4 | −174.73 (10) | C3—C2—N2—O3 | 140.47 (11) |
C2—C3—C4—C5 | 0.50 (17) | C1—C2—N2—O3 | −34.78 (15) |
C2—C3—C4—Cl1 | 179.11 (8) | O5—C7—C8—O6 | −58.54 (13) |
C3—C4—C5—C6 | −0.58 (18) | O6—C9—C10—O5 | 57.95 (14) |
Cl1—C4—C5—C6 | −179.16 (9) | C8—C7—O5—C10 | 58.67 (13) |
C2—C1—C6—C5 | 1.35 (17) | C9—C10—O5—C7 | −58.31 (13) |
N1—C1—C6—C5 | −173.37 (10) | C10—C9—O6—C8 | −56.48 (14) |
C4—C5—C6—C1 | −0.36 (17) | C7—C8—O6—C9 | 56.69 (13) |
C6—C1—N1—O1 | −47.53 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O5 | 0.938 (15) | 2.331 (15) | 3.2553 (14) | 168.3 (13) |
C5—H5···O4i | 0.969 (17) | 2.697 (18) | 3.6166 (16) | 158.7 (13) |
C6—H6···O6ii | 0.949 (15) | 2.468 (15) | 3.4017 (14) | 168.1 (12) |
C7—H7B···O4 | 0.990 (17) | 2.624 (17) | 3.4618 (16) | 142.5 (13) |
C8—H8B···O1iii | 0.996 (19) | 2.446 (18) | 3.2604 (16) | 138.6 (13) |
C9—H9B···O3iv | 0.951 (18) | 2.649 (18) | 3.5930 (16) | 172.3 (14) |
Symmetry codes: (i) x−1, y, z; (ii) x−1, y−1, z−1; (iii) x+1, y+1, z+1; (iv) x, y+1, z+1. |
Acknowledgements
The authors acknowledge the Research Councils UK Basic Technology Programme for supporting `Control and Prediction of the Organic Solid State' (URL: www.cposs.org.uk).
References
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