The structure of the title compound, C12H11ClN2O2, prepared in a synthetic study on spicamycin derivatives, has been determined. In the crystal structure, the molecules lie on mirror planes and form a herring-bone structure.
Supporting information
CCDC reference: 200751
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.009 Å
- R factor = 0.141
- wR factor = 0.417
- Data-to-parameter ratio = 14.3
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level B:
RFACR_01 Alert B The value of the weighted R factor is > 0.35
Weighted R factor given 0.417
| Author response: Please see the _publ_section_exptl_refinement section.
|
Alert Level C:
RFACG_01 Alert C The value of the R factor is > 0.10
R factor given 0.141
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software (Rigaku, 1999); data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.
Crystal data top
C12H11ClN2O2 | Dx = 1.401 Mg m−3 |
Mr = 250.68 | Mo Kα radiation, λ = 0.7107 Å |
Orthorhombic, Pnma | Cell parameters from 25 reflections |
a = 12.311 (2) Å | θ = 12.0–12.5° |
b = 6.788 (2) Å | µ = 0.31 mm−1 |
c = 14.222 (2) Å | T = 299 K |
V = 1188.5 (4) Å3 | Prism, colourless |
Z = 4 | 0.50 × 0.50 × 0.50 mm |
F(000) = 520.0 | |
Data collection top
Rigaku AFC-7R diffractometer | Rint = 0.024 |
ω–2θ scans | θmax = 27.5° |
Absorption correction: integration (Coppens et al., 1965) | h = −6→15 |
Tmin = 0.861, Tmax = 0.875 | k = −3→8 |
1660 measured reflections | l = 0→18 |
1477 independent reflections | 3 standard reflections every 150 reflections |
1017 reflections with I > 2σ(I) | intensity decay: 3.9% |
Refinement top
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.141 | w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.417 | (Δ/σ)max < 0.001 |
S = 1.79 | Δρmax = 0.43 e Å−3 |
1477 reflections | Δρmin = −1.06 e Å−3 |
103 parameters | |
Special details top
Refinement. X-ray intensity data were measured for +h, +k, +l (θ < 27.5°). Additionally,
the intensity data of +h, -k, +l; -h, -k, +l; and -h, +k, +l were measured (θ
< 11°). However, the crystal specimen moved a little before completing the
data collection, and the reorientation procedure for the setting parameters
failed unfortunately by a shutter error. The observed intensities of almost
all the +h, -k, +l reflections were apparently smaller than the equivalent
reflections. Therefore, the +h, -k, +l reflections were omitted from the
analysis. All the independent reflections were used in the refinement. The
weighted R-factor (wR) and goodness of fit (S) are based
on F2. R-factor (gt) are based on F. The threshold
expression of F2 2.0 σ(F2) is used only for calculating
R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.4717 (2) | 0.2500 | 0.9021 (1) | 0.127 (1) | |
O2 | 0.5141 (3) | 0.2500 | 0.5594 (3) | 0.075 (1) | |
O3 | 0.2294 (5) | 0.2500 | 0.1856 (4) | 0.115 (2) | |
N4 | 0.4988 (4) | 0.2500 | 0.7204 (3) | 0.071 (1) | |
N5 | 0.6569 (4) | 0.2500 | 0.8166 (4) | 0.081 (1) | |
C6 | 0.5531 (4) | 0.2500 | 0.8012 (4) | 0.076 (2) | |
C7 | 0.7173 (5) | 0.2500 | 0.7386 (4) | 0.080 (2) | |
C8 | 0.6717 (5) | 0.2500 | 0.6499 (4) | 0.076 (1) | |
C9 | 0.5605 (4) | 0.2500 | 0.6453 (3) | 0.064 (1) | |
C10 | 0.3984 (5) | 0.2500 | 0.5571 (4) | 0.077 (2) | |
C11 | 0.3607 (4) | 0.2500 | 0.4552 (4) | 0.066 (1) | |
C12 | 0.4306 (5) | 0.2500 | 0.3788 (4) | 0.072 (1) | |
C13 | 0.3895 (5) | 0.2500 | 0.2868 (4) | 0.074 (1) | |
C14 | 0.2801 (6) | 0.2500 | 0.2722 (4) | 0.080 (2) | |
C15 | 0.2087 (6) | 0.2500 | 0.3488 (5) | 0.087 (2) | |
C16 | 0.2504 (5) | 0.2500 | 0.4400 (4) | 0.080 (2) | |
C17 | 0.2978 (10) | 0.2500 | 0.1051 (5) | 0.121 (3) | |
H7 | 0.7942 | 0.2500 | 0.7444 | 0.0959* | |
H8 | 0.7153 | 0.2500 | 0.5948 | 0.0912* | |
H10A | 0.3717 | 0.1357 | 0.5880 | 0.0917* | |
H12 | 0.5069 | 0.2500 | 0.3888 | 0.0858* | |
H13 | 0.4378 | 0.2500 | 0.2348 | 0.0882* | |
H15 | 0.1324 | 0.2500 | 0.3388 | 0.1042* | |
H16 | 0.2021 | 0.2500 | 0.4920 | 0.0965* | |
H17A | 0.3424 | 0.1357 | 0.1058 | 0.1453* | |
H17B | 0.2545 | 0.2500 | 0.0498 | 0.1453* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.074 (1) | 0.259 (3) | 0.049 (1) | 0.0000 | 0.0030 (6) | 0.0000 |
O2 | 0.066 (2) | 0.106 (3) | 0.054 (2) | 0.0000 | −0.004 (2) | 0.0000 |
O3 | 0.112 (4) | 0.174 (6) | 0.059 (3) | 0.0000 | −0.027 (3) | 0.0000 |
N4 | 0.066 (2) | 0.096 (3) | 0.052 (2) | 0.0000 | 0.000 (2) | 0.0000 |
N5 | 0.069 (2) | 0.117 (4) | 0.056 (3) | 0.0000 | −0.007 (2) | 0.0000 |
C6 | 0.061 (3) | 0.114 (4) | 0.052 (3) | 0.0000 | −0.001 (2) | 0.0000 |
C7 | 0.060 (3) | 0.120 (5) | 0.059 (3) | 0.0000 | −0.004 (2) | 0.0000 |
C8 | 0.064 (3) | 0.103 (4) | 0.061 (3) | 0.0000 | 0.003 (2) | 0.0000 |
C9 | 0.070 (3) | 0.077 (3) | 0.045 (2) | 0.0000 | −0.006 (2) | 0.0000 |
C10 | 0.062 (3) | 0.109 (4) | 0.059 (3) | 0.0000 | −0.007 (2) | 0.0000 |
C11 | 0.070 (3) | 0.075 (3) | 0.052 (3) | 0.0000 | −0.002 (2) | 0.0000 |
C12 | 0.078 (3) | 0.081 (3) | 0.055 (3) | 0.0000 | −0.005 (2) | 0.0000 |
C13 | 0.083 (4) | 0.082 (3) | 0.056 (3) | 0.0000 | 0.005 (2) | 0.0000 |
C14 | 0.085 (4) | 0.101 (4) | 0.055 (3) | 0.0000 | −0.013 (3) | 0.0000 |
C15 | 0.071 (3) | 0.120 (5) | 0.069 (4) | 0.0000 | −0.011 (3) | 0.0000 |
C16 | 0.071 (3) | 0.114 (5) | 0.056 (3) | 0.0000 | −0.006 (3) | 0.0000 |
C17 | 0.158 (9) | 0.158 (7) | 0.047 (4) | 0.0000 | −0.022 (4) | 0.0000 |
Geometric parameters (Å, º) top
Cl1—C6 | 1.751 (6) | C10—H10Ai | 0.950 |
O2—C9 | 1.349 (6) | C11—C12 | 1.386 (8) |
O2—C10 | 1.426 (7) | C11—C16 | 1.375 (8) |
O3—C14 | 1.381 (8) | C12—C13 | 1.403 (8) |
O3—C17 | 1.42 (1) | C12—H12 | 0.950 |
N4—C6 | 1.330 (7) | C13—C14 | 1.362 (9) |
N4—C9 | 1.310 (6) | C13—H13 | 0.950 |
N5—C6 | 1.296 (8) | C14—C15 | 1.400 (9) |
N5—C7 | 1.336 (8) | C15—C16 | 1.394 (9) |
C7—C8 | 1.381 (8) | C15—H15 | 0.949 |
C7—H7 | 0.950 | C16—H16 | 0.950 |
C8—C9 | 1.370 (8) | C17—H17A | 0.950 |
C8—H8 | 0.950 | C17—H17Ai | 0.950 |
C10—C11 | 1.522 (8) | C17—H17B | 0.950 |
C10—H10A | 0.950 | | |
| | | |
C9—O2—C10 | 116.4 (4) | C10—C11—C16 | 116.8 (5) |
C14—O3—C17 | 116.8 (7) | C12—C11—C16 | 119.3 (5) |
C6—N4—C9 | 114.4 (5) | C11—C12—C13 | 120.5 (6) |
C6—N5—C7 | 114.1 (5) | C11—C12—H12 | 119.8 |
Cl1—C6—N4 | 114.9 (4) | C13—C12—H12 | 119.8 |
Cl1—C6—N5 | 115.2 (4) | C12—C13—C14 | 119.9 (5) |
N4—C6—N5 | 129.9 (5) | C12—C13—H13 | 120.0 |
N5—C7—C8 | 122.2 (5) | C14—C13—H13 | 120.1 |
N5—C7—H7 | 118.9 | O3—C14—C13 | 125.6 (6) |
C8—C7—H7 | 118.9 | O3—C14—C15 | 114.2 (6) |
C7—C8—C9 | 116.7 (5) | C13—C14—C15 | 120.2 (6) |
C7—C8—H8 | 121.6 | C14—C15—C16 | 119.5 (6) |
C9—C8—H8 | 121.7 | C14—C15—H15 | 120.3 |
O2—C9—N4 | 119.5 (5) | C16—C15—H15 | 120.3 |
O2—C9—C8 | 117.8 (5) | C11—C16—C15 | 120.7 (6) |
N4—C9—C8 | 122.7 (5) | C11—C16—H16 | 119.7 |
O2—C10—C11 | 109.1 (5) | C15—C16—H16 | 119.6 |
O2—C10—H10A | 109.5 | O3—C17—H17A | 109.5 |
O2—C10—H10Ai | 109.5 | O3—C17—H17Ai | 109.5 |
C11—C10—H10A | 109.6 | O3—C17—H17B | 109.5 |
C11—C10—H10Ai | 109.6 | H17A—C17—H17Ai | 109.4 |
H10A—C10—H10Ai | 109.4 | H17A—C17—H17B | 109.5 |
C10—C11—C12 | 123.9 (5) | H17Ai—C17—H17B | 109.5 |
Symmetry code: (i) x, −y+1/2, z. |