Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051410/tk2199sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051410/tk2199Isup2.hkl |
CCDC reference: 667428
Key indicators
- Single-crystal X-ray study
- T = 193 K
- Mean (C-C)= 0.003 Å
- R factor = 0.049
- wR factor = 0.111
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
For general background, see: Hu et al. (2005). For related structures, see: Meng et al. (2007); Shi (2005).
4-Chlorobenzaldehyde (7 g, 0.1 mol) and ethyl hydrazinecarboxylate (5.2 g 0.05 mol) were dissolved in a stirred methanol (50 ml) solution and left to stand for 3 h at room temperature. The resulting solid was filtered off and recrystallized from an ethanol solution to yield (I) in 80% yield. Crystals suitable for X-ray analysis were obtained by the slow evaporation of an ethanol solution of (I) held at room temperature; m.p. 463–465 K.
The H atoms were included in the riding model approximation with N—H = 0.88 Å and C—H = 0.95–0.99 Å, and with Uiso(H) = 1.2–1.5Ueq(N, C).
Chlorobenzaldehydehydrazone derivatives are important intermediates in the synthesis of 1,4-dihydrotetrazines, which demonstrate anti-tumour activity (Hu et al., 2005). A representative crystal structure, namely methyl (E)-2-(4-chlorobenzylidene)hydrazinecarboxylate has been reported recently (Meng et al., 2007). Herein, the crystal structure of the title compound, C10H11ClN3O2 (I), is described.
Compound (I) crystallizes with two chemically equivalent but crystallographically independent molecules in the asymmetric unit (Fig. 1). Each essentially planar molecule is in an E-conformation with respect to the N=C double bond. The bond lengths and angles defining the C=N—N(H)—C groups are close to those of the reported literature (Shi, 2005).
Intermolecular N—H···O hydrogen bonds (Table 1) serve to link molecules into a 1-D chain aligned along the (101) direction (Fig. 2).
For general background, see: Hu et al. (2005). For related structures, see: Meng et al. (2007); Shi (2005).
Data collection: CrystalClear (Rigaku, 2001); cell refinement: CrystalClear (Rigaku, 2001); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL (Bruker, 1998).
C10H11ClN2O2 | F(000) = 944 |
Mr = 226.66 | Dx = 1.364 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: -P 2yn | Cell parameters from 7392 reflections |
a = 16.317 (4) Å | θ = 3.3–25.3° |
b = 8.3488 (16) Å | µ = 0.33 mm−1 |
c = 18.035 (4) Å | T = 193 K |
β = 116.014 (4)° | Block, colourless |
V = 2207.9 (8) Å3 | 0.60 × 0.58 × 0.34 mm |
Z = 8 |
Rigaku Mercury diffractometer | 4011 independent reflections |
Radiation source: fine-focus sealed tube | 3479 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
Detector resolution: 7.31 pixels mm-1 | θmax = 25.4°, θmin = 3.3° |
ω scans | h = −19→19 |
Absorption correction: multi-scan (Jacobson, 1998) | k = −10→10 |
Tmin = 0.815, Tmax = 0.895 | l = −19→21 |
20629 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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.16 | w = 1/[σ2(Fo2) + (0.0427P)2 + 0.8029P] where P = (Fo2 + 2Fc2)/3 |
4011 reflections | (Δ/σ)max = 0.001 |
274 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
C10H11ClN2O2 | V = 2207.9 (8) Å3 |
Mr = 226.66 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 16.317 (4) Å | µ = 0.33 mm−1 |
b = 8.3488 (16) Å | T = 193 K |
c = 18.035 (4) Å | 0.60 × 0.58 × 0.34 mm |
β = 116.014 (4)° |
Rigaku Mercury diffractometer | 4011 independent reflections |
Absorption correction: multi-scan (Jacobson, 1998) | 3479 reflections with I > 2σ(I) |
Tmin = 0.815, Tmax = 0.895 | Rint = 0.033 |
20629 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.16 | Δρmax = 0.18 e Å−3 |
4011 reflections | Δρmin = −0.28 e Å−3 |
274 parameters |
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 | 0.25050 (5) | 0.58597 (9) | 0.64513 (4) | 0.0635 (2) | |
Cl2 | 0.45783 (5) | 0.27646 (10) | 0.86369 (4) | 0.0694 (2) | |
O1 | 0.51197 (9) | 0.07441 (18) | 0.36647 (8) | 0.0386 (4) | |
O2 | 0.66600 (9) | 0.06493 (19) | 0.42539 (8) | 0.0406 (4) | |
O3 | 0.78957 (10) | 0.28077 (19) | 0.58583 (9) | 0.0439 (4) | |
O4 | 0.94280 (9) | 0.30084 (18) | 0.65519 (8) | 0.0399 (4) | |
N1 | 0.52594 (11) | 0.2415 (2) | 0.50250 (10) | 0.0335 (4) | |
N2 | 0.60003 (11) | 0.1871 (2) | 0.49262 (10) | 0.0356 (4) | |
H2A | 0.6558 | 0.2044 | 0.5309 | 0.043* | |
N3 | 0.78486 (11) | 0.2701 (2) | 0.73588 (10) | 0.0344 (4) | |
N4 | 0.86403 (11) | 0.2841 (2) | 0.72690 (10) | 0.0355 (4) | |
H4 | 0.9173 | 0.2903 | 0.7704 | 0.043* | |
C1 | 0.47229 (13) | 0.3898 (2) | 0.58521 (12) | 0.0324 (5) | |
C2 | 0.49353 (14) | 0.4774 (3) | 0.65635 (12) | 0.0372 (5) | |
H2B | 0.5557 | 0.4960 | 0.6930 | 0.045* | |
C3 | 0.42629 (15) | 0.5386 (3) | 0.67540 (13) | 0.0421 (5) | |
H3 | 0.4419 | 0.5977 | 0.7248 | 0.051* | |
C4 | 0.33623 (15) | 0.5122 (3) | 0.62145 (13) | 0.0410 (5) | |
C5 | 0.31250 (15) | 0.4279 (3) | 0.54926 (14) | 0.0439 (5) | |
H5 | 0.2502 | 0.4120 | 0.5123 | 0.053* | |
C6 | 0.38014 (14) | 0.3673 (3) | 0.53144 (13) | 0.0394 (5) | |
H6 | 0.3640 | 0.3090 | 0.4817 | 0.047* | |
C7 | 0.54462 (14) | 0.3241 (2) | 0.56740 (12) | 0.0348 (5) | |
H7 | 0.6065 | 0.3431 | 0.6047 | 0.042* | |
C8 | 0.58569 (13) | 0.1065 (2) | 0.42305 (12) | 0.0334 (5) | |
C9 | 0.66132 (15) | −0.0179 (3) | 0.35306 (13) | 0.0456 (6) | |
H9A | 0.6314 | 0.0506 | 0.3036 | 0.055* | |
H9B | 0.6256 | −0.1180 | 0.3440 | 0.055* | |
C10 | 0.75707 (17) | −0.0554 (4) | 0.36796 (16) | 0.0643 (8) | |
H10A | 0.7922 | 0.0442 | 0.3785 | 0.096* | |
H10B | 0.7564 | −0.1086 | 0.3193 | 0.096* | |
H10C | 0.7852 | −0.1263 | 0.4159 | 0.096* | |
C11 | 0.71148 (13) | 0.2927 (2) | 0.82341 (12) | 0.0323 (5) | |
C12 | 0.70356 (15) | 0.3895 (3) | 0.88275 (13) | 0.0415 (5) | |
H12 | 0.7520 | 0.4600 | 0.9147 | 0.050* | |
C13 | 0.62641 (16) | 0.3846 (3) | 0.89583 (13) | 0.0452 (6) | |
H13 | 0.6210 | 0.4527 | 0.9356 | 0.054* | |
C14 | 0.55750 (15) | 0.2798 (3) | 0.85064 (13) | 0.0420 (5) | |
C15 | 0.56525 (15) | 0.1782 (3) | 0.79387 (13) | 0.0404 (5) | |
H15 | 0.5182 | 0.1033 | 0.7646 | 0.049* | |
C16 | 0.64155 (14) | 0.1859 (3) | 0.77987 (13) | 0.0360 (5) | |
H16 | 0.6464 | 0.1174 | 0.7400 | 0.043* | |
C17 | 0.79131 (14) | 0.3070 (2) | 0.80711 (13) | 0.0364 (5) | |
H17 | 0.8477 | 0.3436 | 0.8491 | 0.044* | |
C18 | 0.85828 (13) | 0.2881 (2) | 0.64994 (12) | 0.0342 (5) | |
C19 | 0.94907 (16) | 0.3227 (3) | 0.57822 (14) | 0.0495 (6) | |
H19A | 0.9280 | 0.4313 | 0.5559 | 0.059* | |
H19B | 0.9106 | 0.2430 | 0.5370 | 0.059* | |
C20 | 1.04581 (19) | 0.3012 (5) | 0.59608 (18) | 0.0784 (10) | |
H20A | 1.0833 | 0.3787 | 0.6381 | 0.118* | |
H20B | 1.0531 | 0.3184 | 0.5456 | 0.118* | |
H20C | 1.0652 | 0.1922 | 0.6164 | 0.118* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0598 (4) | 0.0750 (5) | 0.0709 (4) | 0.0098 (3) | 0.0425 (4) | −0.0035 (3) |
Cl2 | 0.0548 (4) | 0.0933 (6) | 0.0770 (5) | 0.0089 (4) | 0.0444 (4) | 0.0090 (4) |
O1 | 0.0262 (8) | 0.0470 (9) | 0.0341 (8) | 0.0033 (6) | 0.0054 (6) | −0.0007 (7) |
O2 | 0.0273 (7) | 0.0576 (10) | 0.0337 (8) | 0.0065 (7) | 0.0105 (6) | −0.0048 (7) |
O3 | 0.0292 (8) | 0.0578 (10) | 0.0349 (8) | −0.0052 (7) | 0.0049 (7) | 0.0003 (7) |
O4 | 0.0271 (8) | 0.0544 (10) | 0.0362 (8) | 0.0003 (7) | 0.0119 (6) | 0.0004 (7) |
N1 | 0.0278 (9) | 0.0369 (10) | 0.0332 (9) | 0.0025 (7) | 0.0110 (7) | 0.0022 (8) |
N2 | 0.0222 (8) | 0.0480 (11) | 0.0309 (9) | 0.0025 (8) | 0.0065 (7) | −0.0023 (8) |
N3 | 0.0256 (9) | 0.0348 (10) | 0.0391 (10) | −0.0003 (7) | 0.0108 (7) | 0.0035 (8) |
N4 | 0.0236 (9) | 0.0441 (11) | 0.0337 (10) | −0.0005 (7) | 0.0076 (7) | 0.0030 (8) |
C1 | 0.0319 (11) | 0.0303 (11) | 0.0326 (11) | −0.0002 (9) | 0.0120 (9) | 0.0034 (9) |
C2 | 0.0355 (11) | 0.0365 (12) | 0.0332 (11) | −0.0007 (9) | 0.0092 (9) | −0.0003 (9) |
C3 | 0.0510 (14) | 0.0383 (12) | 0.0353 (12) | 0.0012 (10) | 0.0174 (10) | −0.0024 (10) |
C4 | 0.0439 (13) | 0.0397 (12) | 0.0443 (13) | 0.0059 (10) | 0.0239 (11) | 0.0053 (10) |
C5 | 0.0328 (12) | 0.0509 (14) | 0.0458 (13) | −0.0012 (10) | 0.0152 (10) | −0.0011 (11) |
C6 | 0.0356 (12) | 0.0455 (13) | 0.0336 (11) | −0.0016 (10) | 0.0119 (9) | −0.0050 (10) |
C7 | 0.0291 (11) | 0.0370 (12) | 0.0320 (11) | −0.0009 (9) | 0.0077 (9) | 0.0029 (9) |
C8 | 0.0275 (11) | 0.0364 (11) | 0.0330 (11) | 0.0041 (9) | 0.0102 (9) | 0.0055 (9) |
C9 | 0.0393 (13) | 0.0608 (15) | 0.0342 (12) | 0.0097 (11) | 0.0140 (10) | −0.0017 (11) |
C10 | 0.0471 (15) | 0.095 (2) | 0.0555 (16) | 0.0135 (14) | 0.0271 (13) | −0.0069 (15) |
C11 | 0.0288 (10) | 0.0314 (11) | 0.0312 (10) | 0.0001 (9) | 0.0080 (8) | 0.0035 (9) |
C12 | 0.0407 (12) | 0.0396 (13) | 0.0348 (11) | −0.0039 (10) | 0.0078 (10) | −0.0029 (10) |
C13 | 0.0535 (14) | 0.0468 (14) | 0.0364 (12) | 0.0077 (11) | 0.0206 (11) | −0.0016 (10) |
C14 | 0.0378 (12) | 0.0498 (14) | 0.0420 (12) | 0.0069 (10) | 0.0206 (10) | 0.0090 (11) |
C15 | 0.0340 (12) | 0.0414 (13) | 0.0436 (12) | −0.0045 (10) | 0.0149 (10) | 0.0019 (10) |
C16 | 0.0343 (11) | 0.0341 (12) | 0.0376 (11) | −0.0012 (9) | 0.0140 (9) | 0.0000 (9) |
C17 | 0.0300 (11) | 0.0365 (12) | 0.0350 (12) | −0.0032 (9) | 0.0072 (9) | 0.0020 (9) |
C18 | 0.0262 (11) | 0.0328 (11) | 0.0378 (12) | 0.0005 (8) | 0.0087 (9) | 0.0012 (9) |
C19 | 0.0460 (14) | 0.0630 (16) | 0.0424 (13) | −0.0040 (12) | 0.0221 (11) | 0.0002 (11) |
C20 | 0.0536 (17) | 0.128 (3) | 0.0668 (18) | 0.0082 (18) | 0.0388 (15) | 0.0068 (18) |
Cl1—C4 | 1.744 (2) | C6—H6 | 0.9500 |
Cl2—C14 | 1.743 (2) | C7—H7 | 0.9500 |
O1—C8 | 1.218 (2) | C9—C10 | 1.498 (3) |
O2—C8 | 1.338 (2) | C9—H9A | 0.9900 |
O2—C9 | 1.449 (3) | C9—H9B | 0.9900 |
O3—C18 | 1.209 (2) | C10—H10A | 0.9800 |
O4—C18 | 1.344 (2) | C10—H10B | 0.9800 |
O4—C19 | 1.447 (3) | C10—H10C | 0.9800 |
N1—C7 | 1.275 (3) | C11—C16 | 1.388 (3) |
N1—N2 | 1.374 (2) | C11—C12 | 1.392 (3) |
N2—C8 | 1.350 (3) | C11—C17 | 1.460 (3) |
N2—H2A | 0.8800 | C12—C13 | 1.379 (3) |
N3—C17 | 1.280 (3) | C12—H12 | 0.9500 |
N3—N4 | 1.376 (2) | C13—C14 | 1.375 (3) |
N4—C18 | 1.350 (3) | C13—H13 | 0.9500 |
N4—H4 | 0.8800 | C14—C15 | 1.377 (3) |
C1—C2 | 1.383 (3) | C15—C16 | 1.376 (3) |
C1—C6 | 1.399 (3) | C15—H15 | 0.9500 |
C1—C7 | 1.459 (3) | C16—H16 | 0.9500 |
C2—C3 | 1.383 (3) | C17—H17 | 0.9500 |
C2—H2B | 0.9500 | C19—C20 | 1.477 (3) |
C3—C4 | 1.378 (3) | C19—H19A | 0.9900 |
C3—H3 | 0.9500 | C19—H19B | 0.9900 |
C4—C5 | 1.378 (3) | C20—H20A | 0.9800 |
C5—C6 | 1.374 (3) | C20—H20B | 0.9800 |
C5—H5 | 0.9500 | C20—H20C | 0.9800 |
C8—O2—C9 | 115.55 (15) | C9—C10—H10B | 109.5 |
C18—O4—C19 | 116.37 (16) | H10A—C10—H10B | 109.5 |
C7—N1—N2 | 115.36 (16) | C9—C10—H10C | 109.5 |
C8—N2—N1 | 118.78 (16) | H10A—C10—H10C | 109.5 |
C8—N2—H2A | 120.6 | H10B—C10—H10C | 109.5 |
N1—N2—H2A | 120.6 | C16—C11—C12 | 118.5 (2) |
C17—N3—N4 | 115.44 (16) | C16—C11—C17 | 121.55 (19) |
C18—N4—N3 | 118.54 (16) | C12—C11—C17 | 119.93 (18) |
C18—N4—H4 | 120.7 | C13—C12—C11 | 120.9 (2) |
N3—N4—H4 | 120.7 | C13—C12—H12 | 119.5 |
C2—C1—C6 | 118.04 (19) | C11—C12—H12 | 119.5 |
C2—C1—C7 | 120.36 (18) | C14—C13—C12 | 119.2 (2) |
C6—C1—C7 | 121.60 (19) | C14—C13—H13 | 120.4 |
C1—C2—C3 | 121.51 (19) | C12—C13—H13 | 120.4 |
C1—C2—H2B | 119.2 | C13—C14—C15 | 121.0 (2) |
C3—C2—H2B | 119.2 | C13—C14—Cl2 | 119.94 (18) |
C4—C3—C2 | 118.8 (2) | C15—C14—Cl2 | 119.08 (18) |
C4—C3—H3 | 120.6 | C16—C15—C14 | 119.5 (2) |
C2—C3—H3 | 120.6 | C16—C15—H15 | 120.2 |
C5—C4—C3 | 121.3 (2) | C14—C15—H15 | 120.2 |
C5—C4—Cl1 | 119.24 (17) | C15—C16—C11 | 120.8 (2) |
C3—C4—Cl1 | 119.46 (17) | C15—C16—H16 | 119.6 |
C6—C5—C4 | 119.2 (2) | C11—C16—H16 | 119.6 |
C6—C5—H5 | 120.4 | N3—C17—C11 | 119.62 (18) |
C4—C5—H5 | 120.4 | N3—C17—H17 | 120.2 |
C5—C6—C1 | 121.2 (2) | C11—C17—H17 | 120.2 |
C5—C6—H6 | 119.4 | O3—C18—O4 | 124.32 (19) |
C1—C6—H6 | 119.4 | O3—C18—N4 | 126.83 (19) |
N1—C7—C1 | 120.97 (18) | O4—C18—N4 | 108.85 (16) |
N1—C7—H7 | 119.5 | O4—C19—C20 | 107.08 (19) |
C1—C7—H7 | 119.5 | O4—C19—H19A | 110.3 |
O1—C8—O2 | 124.26 (19) | C20—C19—H19A | 110.3 |
O1—C8—N2 | 126.37 (18) | O4—C19—H19B | 110.3 |
O2—C8—N2 | 109.37 (16) | C20—C19—H19B | 110.3 |
O2—C9—C10 | 107.41 (18) | H19A—C19—H19B | 108.6 |
O2—C9—H9A | 110.2 | C19—C20—H20A | 109.5 |
C10—C9—H9A | 110.2 | C19—C20—H20B | 109.5 |
O2—C9—H9B | 110.2 | H20A—C20—H20B | 109.5 |
C10—C9—H9B | 110.2 | C19—C20—H20C | 109.5 |
H9A—C9—H9B | 108.5 | H20A—C20—H20C | 109.5 |
C9—C10—H10A | 109.5 | H20B—C20—H20C | 109.5 |
C7—N1—N2—C8 | −176.30 (18) | C8—O2—C9—C10 | −179.4 (2) |
C17—N3—N4—C18 | −163.06 (19) | C16—C11—C12—C13 | −2.6 (3) |
C6—C1—C2—C3 | 1.4 (3) | C17—C11—C12—C13 | 176.24 (19) |
C7—C1—C2—C3 | −178.84 (19) | C11—C12—C13—C14 | 1.4 (3) |
C1—C2—C3—C4 | −0.6 (3) | C12—C13—C14—C15 | 1.2 (3) |
C2—C3—C4—C5 | −0.6 (3) | C12—C13—C14—Cl2 | −177.80 (17) |
C2—C3—C4—Cl1 | 179.09 (17) | C13—C14—C15—C16 | −2.5 (3) |
C3—C4—C5—C6 | 0.9 (3) | Cl2—C14—C15—C16 | 176.50 (16) |
Cl1—C4—C5—C6 | −178.77 (17) | C14—C15—C16—C11 | 1.2 (3) |
C4—C5—C6—C1 | 0.0 (3) | C12—C11—C16—C15 | 1.3 (3) |
C2—C1—C6—C5 | −1.1 (3) | C17—C11—C16—C15 | −177.55 (19) |
C7—C1—C6—C5 | 179.2 (2) | N4—N3—C17—C11 | −178.62 (17) |
N2—N1—C7—C1 | 179.72 (17) | C16—C11—C17—N3 | 25.9 (3) |
C2—C1—C7—N1 | 179.19 (19) | C12—C11—C17—N3 | −152.9 (2) |
C6—C1—C7—N1 | −1.1 (3) | C19—O4—C18—O3 | 6.3 (3) |
C9—O2—C8—O1 | 2.5 (3) | C19—O4—C18—N4 | −174.11 (18) |
C9—O2—C8—N2 | −177.92 (18) | N3—N4—C18—O3 | 0.1 (3) |
N1—N2—C8—O1 | −0.7 (3) | N3—N4—C18—O4 | −179.55 (16) |
N1—N2—C8—O2 | 179.73 (16) | C18—O4—C19—C20 | −168.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O1i | 0.88 | 2.08 | 2.869 (2) | 149 |
N2—H2A···O3 | 0.88 | 2.06 | 2.905 (2) | 160 |
Symmetry code: (i) x+1/2, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C10H11ClN2O2 |
Mr | 226.66 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 193 |
a, b, c (Å) | 16.317 (4), 8.3488 (16), 18.035 (4) |
β (°) | 116.014 (4) |
V (Å3) | 2207.9 (8) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.33 |
Crystal size (mm) | 0.60 × 0.58 × 0.34 |
Data collection | |
Diffractometer | Rigaku Mercury |
Absorption correction | Multi-scan (Jacobson, 1998) |
Tmin, Tmax | 0.815, 0.895 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20629, 4011, 3479 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.604 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.111, 1.16 |
No. of reflections | 4011 |
No. of parameters | 274 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.28 |
Computer programs: CrystalClear (Rigaku, 2001), CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998).
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O1i | 0.88 | 2.08 | 2.869 (2) | 149 |
N2—H2A···O3 | 0.88 | 2.06 | 2.905 (2) | 160 |
Symmetry code: (i) x+1/2, −y+1/2, z+1/2. |
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Chlorobenzaldehydehydrazone derivatives are important intermediates in the synthesis of 1,4-dihydrotetrazines, which demonstrate anti-tumour activity (Hu et al., 2005). A representative crystal structure, namely methyl (E)-2-(4-chlorobenzylidene)hydrazinecarboxylate has been reported recently (Meng et al., 2007). Herein, the crystal structure of the title compound, C10H11ClN3O2 (I), is described.
Compound (I) crystallizes with two chemically equivalent but crystallographically independent molecules in the asymmetric unit (Fig. 1). Each essentially planar molecule is in an E-conformation with respect to the N=C double bond. The bond lengths and angles defining the C=N—N(H)—C groups are close to those of the reported literature (Shi, 2005).
Intermolecular N—H···O hydrogen bonds (Table 1) serve to link molecules into a 1-D chain aligned along the (101) direction (Fig. 2).