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In the racemic crystals of (1
S,2
R)- or (1
R,2
S)-1-[
N-(chloroacetyl)carbamoylamino]-2,3-dihydro-1
H-inden-2-yl chloroacetate, C
14H
14Cl
2N
2O
4, (I), the enantiomeric molecules form a dimeric structure
via the N—H
O cyclic hydrogen bond of the carbamoyl moieties. In the chiral crystals of (—)-(1
S,2
R)-1-[
N-(chloroacetyl)carbamoylamino]-2,3-dihydro-1
H-inden-2-yl chloroacetate, C
14H
14Cl
2N
2O
4, (II), the N—H
O intermolecular hydrogen bond forms a zigzag chain around the twofold screw axis. The melting points and calculated densities of (I) and (II) are 446 and 396 K, and 1.481 and 1.445 Mg m
−3, respectively.
Supporting information
CCDC references: 153918; 153919
For both compounds, data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); 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
C14H14Cl2N2O4 | Z = 2 |
Mr = 345.18 | Dx = 1.481 Mg m−3 |
Triclinic, P1 | Melting point: 446 K |
a = 10.017 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 16.575 (6) Å | Cell parameters from 25 reflections |
c = 4.883 (3) Å | θ = 14.3–15.0° |
α = 95.63 (3)° | µ = 0.44 mm−1 |
β = 90.84 (4)° | T = 298 K |
γ = 106.28 (3)° | Needle, colourless |
V = 773.8 (6) Å3 | 0.60 × 0.10 × 0.05 mm |
Data collection top
Rigaku AFC-7R diffractometer | Rint = 0.021 |
ω scans | θmax = 27.5°, θmin = 2.5° |
Absorption correction: integration (Coppens et al., 1965) | h = −13→13 |
Tmin = 0.916, Tmax = 0.979 | k = −22→22 |
3951 measured reflections | l = 0→6 |
3536 independent reflections | 3 standard reflections every 150 reflections |
2066 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.051 | w = 1/[σ2(Fo2) + (0.0588P)2 + 0.3077P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.141 | (Δ/σ)max = 0.001 |
S = 1.02 | Δρmax = 0.51 e Å−3 |
3536 reflections | Δρmin = −0.31 e Å−3 |
208 parameters | |
Special details top
Refinement. Refinement was based on F2 against all reflections. The weighted
R-factor (wR) and goodness of fit (S) were based on
F2, and conventional R-factor (R) was calculated on
F, with F set to zero for negative F2. The threshold
expression of I > 2σ(I) was 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 | 0.1312 (1) | 1.01781 (6) | 0.7967 (2) | 0.0790 (3) | |
Cl2 | −0.3048 (1) | 0.76653 (8) | −0.2329 (3) | 0.1027 (4) | |
O3 | 0.4641 (2) | 0.8967 (1) | −0.1426 (4) | 0.0554 (5) | |
O4 | 0.1663 (2) | 0.8741 (1) | 0.4446 (5) | 0.0622 (6) | |
O5 | 0.0457 (2) | 0.7147 (1) | −0.1336 (4) | 0.0477 (5) | |
O6 | −0.1033 (3) | 0.6845 (2) | −0.5006 (5) | 0.0827 (8) | |
N7 | 0.2942 (3) | 0.8019 (1) | 0.0507 (5) | 0.0466 (6) | |
N8 | 0.3531 (2) | 0.9436 (1) | 0.2149 (5) | 0.0415 (5) | |
C9 | 0.1493 (3) | 0.6902 (2) | −0.3007 (5) | 0.0469 (7) | |
C10 | 0.1247 (3) | 0.5944 (2) | −0.3285 (6) | 0.0522 (7) | |
C11 | 0.2226 (3) | 0.5799 (2) | −0.1167 (6) | 0.0463 (7) | |
C12 | 0.2338 (4) | 0.5042 (2) | −0.0318 (7) | 0.0629 (9) | |
C13 | 0.3331 (5) | 0.5055 (2) | 0.1631 (9) | 0.078 (1) | |
C14 | 0.4248 (4) | 0.5806 (3) | 0.2763 (8) | 0.076 (1) | |
C15 | 0.4174 (3) | 0.6571 (2) | 0.1914 (7) | 0.0594 (8) | |
C16 | 0.3157 (3) | 0.6556 (2) | −0.0063 (6) | 0.0441 (6) | |
C17 | 0.2915 (3) | 0.7286 (2) | −0.1413 (5) | 0.0442 (6) | |
C18 | 0.3745 (3) | 0.8790 (2) | 0.0269 (5) | 0.0387 (6) | |
C19 | 0.2519 (3) | 0.9386 (2) | 0.4008 (6) | 0.0431 (6) | |
C20 | 0.2573 (4) | 1.0246 (2) | 0.5479 (7) | 0.0580 (8) | |
C21 | −0.0721 (4) | 0.7148 (2) | −0.2672 (7) | 0.0579 (8) | |
C22 | −0.1534 (4) | 0.7566 (3) | −0.0749 (9) | 0.084 (1) | |
H7 | 0.235 (3) | 0.801 (2) | 0.154 (6) | 0.0499 (1)* | |
H8 | 0.405 (3) | 0.990 (2) | 0.195 (6) | 0.0516 (1)* | |
H9 | 0.1499 | 0.7108 | −0.4778 | 0.0561* | |
H10A | 0.0304 | 0.5656 | −0.2971 | 0.0631* | |
H10B | 0.1454 | 0.5743 | −0.5106 | 0.0631* | |
H12 | 0.1711 | 0.4514 | −0.1101 | 0.0769* | |
H13 | 0.3403 | 0.4538 | 0.2255 | 0.0945* | |
H14 | 0.4969 | 0.5804 | 0.4116 | 0.0910* | |
H15 | 0.4808 | 0.7096 | 0.2701 | 0.0734* | |
H17 | 0.3622 | 0.7451 | −0.2711 | 0.0523* | |
H20A | 0.3476 | 1.0496 | 0.6332 | 0.0712* | |
H20B | 0.2421 | 1.0603 | 0.4137 | 0.0712* | |
H22A | −0.0960 | 0.8118 | −0.0041 | 0.1013* | |
H22B | −0.1784 | 0.7242 | 0.0794 | 0.1013* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0800 (6) | 0.0874 (6) | 0.0719 (6) | 0.0342 (5) | 0.0158 (5) | −0.0135 (5) |
Cl2 | 0.0599 (6) | 0.1116 (9) | 0.141 (1) | 0.0236 (5) | −0.0187 (6) | 0.0410 (8) |
O3 | 0.053 (1) | 0.0318 (9) | 0.073 (1) | −0.0011 (8) | 0.025 (1) | −0.0020 (9) |
O4 | 0.069 (1) | 0.039 (1) | 0.071 (1) | 0.0019 (10) | 0.028 (1) | 0.0015 (10) |
O5 | 0.058 (1) | 0.045 (1) | 0.039 (1) | 0.0157 (9) | −0.0066 (9) | −0.0010 (8) |
O6 | 0.097 (2) | 0.087 (2) | 0.056 (1) | 0.019 (1) | −0.029 (1) | −0.006 (1) |
N7 | 0.058 (1) | 0.028 (1) | 0.045 (1) | −0.0016 (10) | 0.017 (1) | −0.0017 (9) |
N8 | 0.044 (1) | 0.024 (1) | 0.050 (1) | 0.0001 (9) | 0.006 (1) | 0.0003 (9) |
C9 | 0.066 (2) | 0.034 (1) | 0.034 (1) | 0.004 (1) | 0.008 (1) | 0.000 (1) |
C10 | 0.060 (2) | 0.034 (1) | 0.051 (2) | −0.003 (1) | 0.012 (1) | −0.007 (1) |
C11 | 0.057 (2) | 0.030 (1) | 0.047 (2) | 0.006 (1) | 0.019 (1) | −0.002 (1) |
C12 | 0.084 (2) | 0.033 (1) | 0.069 (2) | 0.013 (1) | 0.023 (2) | −0.002 (1) |
C13 | 0.105 (3) | 0.056 (2) | 0.087 (3) | 0.041 (2) | 0.017 (2) | 0.014 (2) |
C14 | 0.080 (2) | 0.079 (3) | 0.080 (3) | 0.041 (2) | −0.001 (2) | 0.005 (2) |
C15 | 0.058 (2) | 0.055 (2) | 0.061 (2) | 0.014 (1) | 0.006 (2) | −0.005 (2) |
C16 | 0.051 (2) | 0.034 (1) | 0.043 (1) | 0.007 (1) | 0.015 (1) | −0.003 (1) |
C17 | 0.053 (2) | 0.029 (1) | 0.043 (1) | −0.001 (1) | 0.015 (1) | −0.001 (1) |
C18 | 0.037 (1) | 0.028 (1) | 0.046 (1) | 0.0025 (10) | 0.001 (1) | 0.001 (1) |
C19 | 0.048 (1) | 0.035 (1) | 0.044 (1) | 0.009 (1) | 0.002 (1) | 0.003 (1) |
C20 | 0.073 (2) | 0.044 (2) | 0.057 (2) | 0.018 (1) | 0.011 (2) | −0.003 (1) |
C21 | 0.071 (2) | 0.041 (2) | 0.056 (2) | 0.009 (1) | −0.016 (2) | 0.007 (1) |
C22 | 0.086 (3) | 0.085 (3) | 0.091 (3) | 0.049 (2) | −0.031 (2) | −0.014 (2) |
Geometric parameters (Å, º) top
Cl1—C20 | 1.754 (4) | C11—C12 | 1.392 (4) |
Cl2—C22 | 1.747 (5) | C11—C16 | 1.391 (3) |
O3—C18 | 1.224 (3) | C12—C13 | 1.360 (6) |
O4—C19 | 1.208 (3) | C12—H12 | 0.962 |
O5—C9 | 1.450 (4) | C13—C14 | 1.381 (5) |
O5—C21 | 1.341 (4) | C13—H13 | 0.959 |
O6—C21 | 1.199 (4) | C14—C15 | 1.393 (6) |
N7—C17 | 1.454 (3) | C14—H14 | 0.972 |
N7—C18 | 1.323 (3) | C15—C16 | 1.386 (4) |
N7—H7 | 0.79 (3) | C15—H15 | 0.962 |
N8—C18 | 1.406 (3) | C16—C17 | 1.507 (4) |
N8—C19 | 1.361 (4) | C17—H17 | 0.957 |
N8—H8 | 0.81 (3) | C19—C20 | 1.519 (4) |
C9—C10 | 1.529 (4) | C20—H20A | 0.953 |
C9—C17 | 1.550 (4) | C20—H20B | 0.963 |
C9—H9 | 0.960 | C21—C22 | 1.495 (6) |
C10—C11 | 1.497 (4) | C22—H22A | 0.961 |
C10—H10A | 0.953 | C22—H22B | 0.963 |
C10—H10B | 0.965 | | |
| | | |
C9—O5—C21 | 116.2 (2) | C14—C15—H15 | 120.6 |
C17—N7—C18 | 123.7 (2) | C16—C15—H15 | 121.1 |
C17—N7—H7 | 122 (2) | C11—C16—C15 | 121.0 (3) |
C18—N7—H7 | 113 (2) | C11—C16—C17 | 110.5 (2) |
C18—N8—C19 | 128.5 (2) | C15—C16—C17 | 128.4 (2) |
C18—N8—H8 | 113 (2) | N7—C17—C9 | 113.0 (2) |
C19—N8—H8 | 119 (2) | N7—C17—C16 | 113.9 (2) |
O5—C9—C10 | 111.2 (2) | N7—C17—H17 | 108.6 |
O5—C9—C17 | 106.8 (2) | C9—C17—C16 | 104.0 (2) |
O5—C9—H9 | 110.2 | C9—C17—H17 | 108.8 |
C10—C9—C17 | 106.0 (2) | C16—C17—H17 | 108.4 |
C10—C9—H9 | 111.3 | O3—C18—N7 | 124.7 (2) |
C17—C9—H9 | 111.2 | O3—C18—N8 | 119.4 (2) |
C9—C10—C11 | 104.8 (2) | N7—C18—N8 | 115.8 (2) |
C9—C10—H10A | 111.4 | O4—C19—N8 | 124.8 (3) |
C9—C10—H10B | 110.8 | O4—C19—C20 | 123.2 (3) |
C11—C10—H10A | 111.4 | N8—C19—C20 | 112.0 (2) |
C11—C10—H10B | 110.5 | Cl1—C20—C19 | 112.1 (2) |
H10A—C10—H10B | 107.9 | Cl1—C20—H20A | 109.6 |
C10—C11—C12 | 129.4 (2) | Cl1—C20—H20B | 109.1 |
C10—C11—C16 | 111.1 (2) | C19—C20—H20A | 109.1 |
C12—C11—C16 | 119.4 (3) | C19—C20—H20B | 108.7 |
C11—C12—C13 | 119.6 (3) | H20A—C20—H20B | 108.1 |
C11—C12—H12 | 119.9 | O5—C21—O6 | 123.7 (3) |
C13—C12—H12 | 120.5 | O5—C21—C22 | 108.4 (3) |
C12—C13—C14 | 121.3 (4) | O6—C21—C22 | 127.9 (4) |
C12—C13—H13 | 120.1 | Cl2—C22—C21 | 112.6 (3) |
C14—C13—H13 | 118.5 | Cl2—C22—H22A | 109.1 |
C13—C14—C15 | 120.2 (4) | Cl2—C22—H22B | 108.9 |
C13—C14—H14 | 120.3 | C21—C22—H22A | 109.3 |
C15—C14—H14 | 119.5 | C21—C22—H22B | 109.3 |
C14—C15—C16 | 118.4 (3) | H22A—C22—H22B | 107.4 |
| | | |
C9—O5—C21—C22 | −169.5 (2) | C17—N7—C18—N8 | 173.7 (3) |
C9—C17—N7—C18 | −115.3 (3) | C17—C9—O5—C21 | 157.2 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N7—H7···O4 | 0.79 (3) | 2.02 (3) | 2.694 (3) | 143 (3) |
N8—H8···O3i | 0.81 (3) | 2.01 (3) | 2.823 (3) | 179 (3) |
Symmetry code: (i) −x+1, −y+2, −z. |
Crystal data top
C14H14Cl2N2O4 | Dx = 1.445 Mg m−3 |
Mr = 345.18 | Melting point: 392 K |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.409 (2) Å | Cell parameters from 22 reflections |
b = 4.595 (2) Å | θ = 10.4–14.5° |
c = 15.667 (1) Å | µ = 0.43 mm−1 |
β = 105.079 (9)° | T = 298 K |
V = 793.1 (3) Å3 | Needle, colourless |
Z = 2 | 0.70 × 0.02 × 0.01 mm |
Data collection top
Rigaku AFC-7R diffractometer | Rint = 0.029 |
ω scans | θmax = 27.5°, θmin = 2.5° |
Absorption correction: integration (Coppens et al., 1965) | h = 0→15 |
Tmin = 0.956, Tmax = 0.991 | k = −6→0 |
2130 measured reflections | l = −20→20 |
2031 independent reflections | 3 standard reflections every 150 reflections |
831 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | w = 1/[σ2(Fo2) + (0.0468P)2 + ] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.057 | (Δ/σ)max = 0.001 |
wR(F2) = 0.126 | Δρmax = 0.24 e Å−3 |
S = 0.97 | Δρmin = −0.24 e Å−3 |
2031 reflections | Absolute structure: Flack (1983) |
208 parameters | Absolute structure parameter: 0.2 (2) |
H atoms treated by a mixture of independent and constrained refinement | |
Special details top
Refinement. Refinement was based on F2 against all reflections. The weighted
R-factor (wR) and goodness of fit (S) were based on
F2, and conventional R-factor (R) was calculated on
F, with F set to zero for negative F2. The threshold
expression of I > 2σ(I) was 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 | 0.8787 (1) | −0.2517 (5) | −0.0263 (1) | 0.0793 (7) | |
Cl2 | 1.2476 (2) | 0.8432 (8) | 0.2536 (1) | 0.129 (1) | |
O3 | 0.5315 (4) | 0.601 (1) | 0.0979 (2) | 0.079 (2) | |
O4 | 0.8493 (4) | 0.142 (1) | 0.1132 (3) | 0.067 (2) | |
O5 | 0.9233 (4) | 0.701 (1) | 0.2743 (2) | 0.066 (1) | |
O6 | 1.0494 (4) | 1.067 (1) | 0.3267 (4) | 0.086 (2) | |
N7 | 0.7191 (4) | 0.507 (1) | 0.1864 (3) | 0.051 (2) | |
N8 | 0.6554 (4) | 0.294 (2) | 0.0483 (3) | 0.055 (2) | |
C9 | 0.8306 (5) | 0.821 (2) | 0.3107 (4) | 0.059 (2) | |
C10 | 0.8519 (6) | 0.733 (3) | 0.4082 (4) | 0.095 (3) | |
C11 | 0.7438 (6) | 0.546 (2) | 0.4114 (4) | 0.064 (2) | |
C12 | 0.7188 (7) | 0.411 (2) | 0.4832 (4) | 0.086 (3) | |
C13 | 0.6164 (8) | 0.244 (3) | 0.4725 (5) | 0.099 (3) | |
C14 | 0.5370 (6) | 0.225 (3) | 0.3902 (6) | 0.103 (3) | |
C15 | 0.5595 (7) | 0.362 (2) | 0.3181 (4) | 0.080 (3) | |
C16 | 0.6638 (6) | 0.522 (2) | 0.3286 (4) | 0.060 (2) | |
C17 | 0.7075 (5) | 0.688 (2) | 0.2590 (4) | 0.054 (2) | |
C18 | 0.6303 (6) | 0.476 (2) | 0.1124 (4) | 0.052 (2) | |
C19 | 0.7592 (6) | 0.139 (2) | 0.0516 (4) | 0.053 (2) | |
C20 | 0.7527 (6) | −0.030 (2) | −0.0331 (4) | 0.068 (2) | |
C21 | 1.0263 (6) | 0.853 (2) | 0.2851 (5) | 0.063 (2) | |
C22 | 1.1012 (6) | 0.711 (3) | 0.2308 (5) | 0.101 (3) | |
H7 | 0.789 (5) | 0.36 (2) | 0.182 (4) | 0.0786 (3)* | |
H8 | 0.594 (5) | 0.28 (2) | 0.007 (4) | 0.0791 (3)* | |
H9 | 0.8287 | 1.0404 | 0.3053 | 0.0709* | |
H10A | 0.8558 | 0.9148 | 0.4443 | 0.1125* | |
H10B | 0.9250 | 0.6392 | 0.4274 | 0.1125* | |
H12 | 0.7727 | 0.4470 | 0.5403 | 0.1036* | |
H13 | 0.6003 | 0.1588 | 0.5214 | 0.1167* | |
H14 | 0.4645 | 0.1300 | 0.3831 | 0.1216* | |
H15 | 0.5035 | 0.3593 | 0.2615 | 0.0961* | |
H17 | 0.6524 | 0.8565 | 0.2368 | 0.0661* | |
H20A | 0.6821 | −0.1339 | −0.0453 | 0.0816* | |
H20B | 0.7470 | 0.1198 | −0.0798 | 0.0816* | |
H22A | 1.0628 | 0.7583 | 0.1699 | 0.1218* | |
H22B | 1.1042 | 0.5222 | 0.2422 | 0.1218* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.066 (1) | 0.089 (2) | 0.084 (1) | −0.002 (1) | 0.0206 (9) | −0.015 (1) |
Cl2 | 0.062 (1) | 0.229 (4) | 0.094 (1) | −0.029 (2) | 0.0181 (10) | −0.025 (2) |
O3 | 0.045 (2) | 0.136 (6) | 0.046 (2) | 0.020 (3) | −0.003 (2) | 0.002 (3) |
O4 | 0.050 (2) | 0.098 (5) | 0.046 (2) | 0.008 (3) | −0.003 (2) | −0.005 (3) |
O5 | 0.047 (2) | 0.080 (4) | 0.061 (3) | −0.001 (3) | 0.000 (2) | −0.013 (3) |
O6 | 0.074 (3) | 0.086 (5) | 0.094 (4) | −0.026 (3) | 0.013 (3) | −0.033 (4) |
N7 | 0.043 (3) | 0.068 (4) | 0.034 (3) | 0.003 (3) | −0.004 (2) | −0.013 (3) |
N8 | 0.033 (3) | 0.091 (6) | 0.034 (3) | 0.000 (4) | −0.002 (2) | −0.004 (4) |
C9 | 0.051 (4) | 0.069 (7) | 0.051 (4) | 0.003 (4) | 0.001 (3) | 0.001 (4) |
C10 | 0.072 (4) | 0.155 (9) | 0.049 (4) | −0.029 (7) | 0.001 (3) | 0.002 (6) |
C11 | 0.061 (4) | 0.084 (6) | 0.041 (4) | 0.011 (5) | 0.006 (3) | 0.003 (4) |
C12 | 0.086 (5) | 0.133 (9) | 0.040 (4) | −0.002 (6) | 0.015 (4) | 0.001 (5) |
C13 | 0.107 (6) | 0.126 (8) | 0.072 (5) | −0.017 (8) | 0.040 (5) | −0.009 (7) |
C14 | 0.082 (5) | 0.151 (10) | 0.086 (6) | −0.033 (8) | 0.041 (5) | −0.032 (8) |
C15 | 0.073 (5) | 0.110 (8) | 0.062 (5) | −0.013 (6) | 0.025 (4) | −0.028 (5) |
C16 | 0.051 (4) | 0.074 (6) | 0.054 (4) | 0.007 (4) | 0.014 (3) | −0.014 (4) |
C17 | 0.047 (3) | 0.062 (6) | 0.045 (4) | 0.008 (4) | 0.000 (3) | −0.003 (4) |
C18 | 0.049 (4) | 0.070 (6) | 0.033 (3) | −0.008 (4) | 0.004 (3) | 0.005 (4) |
C19 | 0.046 (4) | 0.072 (6) | 0.041 (4) | −0.017 (4) | 0.008 (3) | −0.002 (4) |
C20 | 0.066 (4) | 0.087 (7) | 0.048 (4) | −0.003 (5) | 0.007 (3) | 0.002 (5) |
C21 | 0.053 (4) | 0.070 (7) | 0.056 (4) | −0.013 (5) | −0.003 (4) | −0.006 (5) |
C22 | 0.061 (4) | 0.150 (10) | 0.094 (5) | −0.026 (7) | 0.024 (4) | −0.048 (7) |
Geometric parameters (Å, º) top
Cl1—C20 | 1.741 (8) | C11—C12 | 1.38 (1) |
Cl2—C22 | 1.726 (8) | C11—C16 | 1.383 (8) |
O3—C18 | 1.231 (8) | C12—C13 | 1.37 (1) |
O4—C19 | 1.214 (6) | C12—H12 | 0.959 |
O5—C9 | 1.435 (8) | C13—C14 | 1.37 (1) |
O5—C21 | 1.339 (9) | C13—H13 | 0.920 |
O6—C21 | 1.17 (1) | C14—C15 | 1.37 (1) |
N7—C17 | 1.441 (9) | C14—H14 | 0.917 |
N7—C18 | 1.333 (7) | C15—C16 | 1.37 (1) |
N7—H7 | 1.05 (7) | C15—H15 | 0.949 |
N8—C18 | 1.394 (10) | C16—C17 | 1.52 (1) |
N8—C19 | 1.371 (9) | C17—H17 | 1.002 |
N8—H8 | 0.82 (5) | C19—C20 | 1.522 (10) |
C9—C10 | 1.537 (9) | C20—H20A | 0.912 |
C9—C17 | 1.552 (8) | C20—H20B | 0.996 |
C9—H9 | 1.013 | C21—C22 | 1.50 (1) |
C10—C11 | 1.51 (1) | C22—H22A | 0.966 |
C10—H10A | 1.005 | C22—H22B | 0.883 |
C10—H10B | 0.917 | | |
| | | |
C9—O5—C21 | 117.6 (6) | C14—C15—H15 | 122.6 |
C17—N7—C18 | 122.9 (6) | C16—C15—H15 | 118.1 |
C17—N7—H7 | 130 (3) | C11—C16—C15 | 119.8 (7) |
C18—N7—H7 | 107 (3) | C11—C16—C17 | 111.9 (6) |
C18—N8—C19 | 128.6 (5) | C15—C16—C17 | 128.3 (5) |
C18—N8—H8 | 109 (5) | N7—C17—C9 | 112.5 (5) |
C19—N8—H8 | 123 (5) | N7—C17—C16 | 113.1 (6) |
O5—C9—C10 | 110.6 (5) | N7—C17—H17 | 110.5 |
O5—C9—C17 | 107.6 (5) | C9—C17—C16 | 104.1 (5) |
O5—C9—H9 | 110.5 | C9—C17—H17 | 106.2 |
C10—C9—C17 | 107.7 (6) | C16—C17—H17 | 110.1 |
C10—C9—H9 | 109.9 | O3—C18—N7 | 124.2 (6) |
C17—C9—H9 | 110.6 | O3—C18—N8 | 119.8 (5) |
C9—C10—C11 | 105.2 (5) | N7—C18—N8 | 116.0 (6) |
C9—C10—H10A | 108.2 | O4—C19—N8 | 124.6 (6) |
C9—C10—H10B | 110.1 | O4—C19—C20 | 122.6 (6) |
C11—C10—H10A | 111.7 | N8—C19—C20 | 112.8 (5) |
C11—C10—H10B | 113.8 | Cl1—C20—C19 | 113.2 (4) |
H10A—C10—H10B | 107.6 | Cl1—C20—H20A | 112.3 |
C10—C11—C12 | 128.8 (5) | Cl1—C20—H20B | 110.2 |
C10—C11—C16 | 111.1 (6) | C19—C20—H20A | 106.8 |
C12—C11—C16 | 120.1 (7) | C19—C20—H20B | 105.4 |
C11—C12—C13 | 120.2 (6) | H20A—C20—H20B | 108.7 |
C11—C12—H12 | 117.6 | O5—C21—O6 | 124.8 (7) |
C13—C12—H12 | 122.1 | O5—C21—C22 | 108.1 (7) |
C12—C13—C14 | 119.0 (9) | O6—C21—C22 | 127.0 (8) |
C12—C13—H13 | 118.9 | Cl2—C22—C21 | 113.1 (7) |
C14—C13—H13 | 122.0 | Cl2—C22—H22A | 106.8 |
C13—C14—C15 | 121.7 (9) | Cl2—C22—H22B | 108.6 |
C13—C14—H14 | 119.9 | C21—C22—H22A | 106.4 |
C15—C14—H14 | 118.3 | C21—C22—H22B | 108.1 |
C14—C15—C16 | 119.2 (6) | H22A—C22—H22B | 113.9 |
| | | |
C9—O5—C21—C22 | −171.7 (6) | C17—N7—C18—N8 | 180.0 (7) |
C9—C17—N7—C18 | −149.4 (7) | C17—C9—O5—C21 | 156.6 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N7—H7···O4 | 1.05 (7) | 1.75 (7) | 2.688 (8) | 146 (4) |
N8—H8···O3i | 0.82 (5) | 2.05 (6) | 2.837 (6) | 159 (8) |
Symmetry code: (i) −x+1, y−1/2, −z. |
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