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In the racemic crystals of (1S,2R)- or (1R,2S)-1-[N-(chloro­acetyl)­carbamoyl­amino]-2,3-di­hydro-1H-inden-2-yl chloro­acetate, C14H14Cl2N2O4, (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 (—)-(1S,2R)-1-[N-(chloro­acetyl)­carbamoyl­amino]-2,3-di­hydro-1H-inden-2-yl chloro­acetate, C14H14Cl2N2O4, (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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010001129X/gg1022sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010001129X/gg1022Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010001129X/gg1022IIsup3.hkl
Contains datablock II

CCDC references: 153918; 153919

Computing details top

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.

(I) top
Crystal data top
C14H14Cl2N2O4Z = 2
Mr = 345.18Dx = 1.481 Mg m3
Triclinic, P1Melting point: 446 K
a = 10.017 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 16.575 (6) ÅCell parameters from 25 reflections
c = 4.883 (3) Åθ = 14.3–15.0°
α = 95.63 (3)°µ = 0.44 mm1
β = 90.84 (4)°T = 298 K
γ = 106.28 (3)°Needle, colourless
V = 773.8 (6) Å30.60 × 0.10 × 0.05 mm
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.021
ω scansθmax = 27.5°, θmin = 2.5°
Absorption correction: integration
(Coppens et al., 1965)
h = 1313
Tmin = 0.916, Tmax = 0.979k = 2222
3951 measured reflectionsl = 06
3536 independent reflections3 standard reflections every 150 reflections
2066 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2H 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 = 1.02Δρmax = 0.51 e Å3
3536 reflectionsΔρmin = 0.31 e Å3
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
xyzUiso*/Ueq
Cl10.1312 (1)1.01781 (6)0.7967 (2)0.0790 (3)
Cl20.3048 (1)0.76653 (8)0.2329 (3)0.1027 (4)
O30.4641 (2)0.8967 (1)0.1426 (4)0.0554 (5)
O40.1663 (2)0.8741 (1)0.4446 (5)0.0622 (6)
O50.0457 (2)0.7147 (1)0.1336 (4)0.0477 (5)
O60.1033 (3)0.6845 (2)0.5006 (5)0.0827 (8)
N70.2942 (3)0.8019 (1)0.0507 (5)0.0466 (6)
N80.3531 (2)0.9436 (1)0.2149 (5)0.0415 (5)
C90.1493 (3)0.6902 (2)0.3007 (5)0.0469 (7)
C100.1247 (3)0.5944 (2)0.3285 (6)0.0522 (7)
C110.2226 (3)0.5799 (2)0.1167 (6)0.0463 (7)
C120.2338 (4)0.5042 (2)0.0318 (7)0.0629 (9)
C130.3331 (5)0.5055 (2)0.1631 (9)0.078 (1)
C140.4248 (4)0.5806 (3)0.2763 (8)0.076 (1)
C150.4174 (3)0.6571 (2)0.1914 (7)0.0594 (8)
C160.3157 (3)0.6556 (2)0.0063 (6)0.0441 (6)
C170.2915 (3)0.7286 (2)0.1413 (5)0.0442 (6)
C180.3745 (3)0.8790 (2)0.0269 (5)0.0387 (6)
C190.2519 (3)0.9386 (2)0.4008 (6)0.0431 (6)
C200.2573 (4)1.0246 (2)0.5479 (7)0.0580 (8)
C210.0721 (4)0.7148 (2)0.2672 (7)0.0579 (8)
C220.1534 (4)0.7566 (3)0.0749 (9)0.084 (1)
H70.235 (3)0.801 (2)0.154 (6)0.0499 (1)*
H80.405 (3)0.990 (2)0.195 (6)0.0516 (1)*
H90.14990.71080.47780.0561*
H10A0.03040.56560.29710.0631*
H10B0.14540.57430.51060.0631*
H120.17110.45140.11010.0769*
H130.34030.45380.22550.0945*
H140.49690.58040.41160.0910*
H150.48080.70960.27010.0734*
H170.36220.74510.27110.0523*
H20A0.34761.04960.63320.0712*
H20B0.24211.06030.41370.0712*
H22A0.09600.81180.00410.1013*
H22B0.17840.72420.07940.1013*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0800 (6)0.0874 (6)0.0719 (6)0.0342 (5)0.0158 (5)0.0135 (5)
Cl20.0599 (6)0.1116 (9)0.141 (1)0.0236 (5)0.0187 (6)0.0410 (8)
O30.053 (1)0.0318 (9)0.073 (1)0.0011 (8)0.025 (1)0.0020 (9)
O40.069 (1)0.039 (1)0.071 (1)0.0019 (10)0.028 (1)0.0015 (10)
O50.058 (1)0.045 (1)0.039 (1)0.0157 (9)0.0066 (9)0.0010 (8)
O60.097 (2)0.087 (2)0.056 (1)0.019 (1)0.029 (1)0.006 (1)
N70.058 (1)0.028 (1)0.045 (1)0.0016 (10)0.017 (1)0.0017 (9)
N80.044 (1)0.024 (1)0.050 (1)0.0001 (9)0.006 (1)0.0003 (9)
C90.066 (2)0.034 (1)0.034 (1)0.004 (1)0.008 (1)0.000 (1)
C100.060 (2)0.034 (1)0.051 (2)0.003 (1)0.012 (1)0.007 (1)
C110.057 (2)0.030 (1)0.047 (2)0.006 (1)0.019 (1)0.002 (1)
C120.084 (2)0.033 (1)0.069 (2)0.013 (1)0.023 (2)0.002 (1)
C130.105 (3)0.056 (2)0.087 (3)0.041 (2)0.017 (2)0.014 (2)
C140.080 (2)0.079 (3)0.080 (3)0.041 (2)0.001 (2)0.005 (2)
C150.058 (2)0.055 (2)0.061 (2)0.014 (1)0.006 (2)0.005 (2)
C160.051 (2)0.034 (1)0.043 (1)0.007 (1)0.015 (1)0.003 (1)
C170.053 (2)0.029 (1)0.043 (1)0.001 (1)0.015 (1)0.001 (1)
C180.037 (1)0.028 (1)0.046 (1)0.0025 (10)0.001 (1)0.001 (1)
C190.048 (1)0.035 (1)0.044 (1)0.009 (1)0.002 (1)0.003 (1)
C200.073 (2)0.044 (2)0.057 (2)0.018 (1)0.011 (2)0.003 (1)
C210.071 (2)0.041 (2)0.056 (2)0.009 (1)0.016 (2)0.007 (1)
C220.086 (3)0.085 (3)0.091 (3)0.049 (2)0.031 (2)0.014 (2)
Geometric parameters (Å, º) top
Cl1—C201.754 (4)C11—C121.392 (4)
Cl2—C221.747 (5)C11—C161.391 (3)
O3—C181.224 (3)C12—C131.360 (6)
O4—C191.208 (3)C12—H120.962
O5—C91.450 (4)C13—C141.381 (5)
O5—C211.341 (4)C13—H130.959
O6—C211.199 (4)C14—C151.393 (6)
N7—C171.454 (3)C14—H140.972
N7—C181.323 (3)C15—C161.386 (4)
N7—H70.79 (3)C15—H150.962
N8—C181.406 (3)C16—C171.507 (4)
N8—C191.361 (4)C17—H170.957
N8—H80.81 (3)C19—C201.519 (4)
C9—C101.529 (4)C20—H20A0.953
C9—C171.550 (4)C20—H20B0.963
C9—H90.960C21—C221.495 (6)
C10—C111.497 (4)C22—H22A0.961
C10—H10A0.953C22—H22B0.963
C10—H10B0.965
C9—O5—C21116.2 (2)C14—C15—H15120.6
C17—N7—C18123.7 (2)C16—C15—H15121.1
C17—N7—H7122 (2)C11—C16—C15121.0 (3)
C18—N7—H7113 (2)C11—C16—C17110.5 (2)
C18—N8—C19128.5 (2)C15—C16—C17128.4 (2)
C18—N8—H8113 (2)N7—C17—C9113.0 (2)
C19—N8—H8119 (2)N7—C17—C16113.9 (2)
O5—C9—C10111.2 (2)N7—C17—H17108.6
O5—C9—C17106.8 (2)C9—C17—C16104.0 (2)
O5—C9—H9110.2C9—C17—H17108.8
C10—C9—C17106.0 (2)C16—C17—H17108.4
C10—C9—H9111.3O3—C18—N7124.7 (2)
C17—C9—H9111.2O3—C18—N8119.4 (2)
C9—C10—C11104.8 (2)N7—C18—N8115.8 (2)
C9—C10—H10A111.4O4—C19—N8124.8 (3)
C9—C10—H10B110.8O4—C19—C20123.2 (3)
C11—C10—H10A111.4N8—C19—C20112.0 (2)
C11—C10—H10B110.5Cl1—C20—C19112.1 (2)
H10A—C10—H10B107.9Cl1—C20—H20A109.6
C10—C11—C12129.4 (2)Cl1—C20—H20B109.1
C10—C11—C16111.1 (2)C19—C20—H20A109.1
C12—C11—C16119.4 (3)C19—C20—H20B108.7
C11—C12—C13119.6 (3)H20A—C20—H20B108.1
C11—C12—H12119.9O5—C21—O6123.7 (3)
C13—C12—H12120.5O5—C21—C22108.4 (3)
C12—C13—C14121.3 (4)O6—C21—C22127.9 (4)
C12—C13—H13120.1Cl2—C22—C21112.6 (3)
C14—C13—H13118.5Cl2—C22—H22A109.1
C13—C14—C15120.2 (4)Cl2—C22—H22B108.9
C13—C14—H14120.3C21—C22—H22A109.3
C15—C14—H14119.5C21—C22—H22B109.3
C14—C15—C16118.4 (3)H22A—C22—H22B107.4
C9—O5—C21—C22169.5 (2)C17—N7—C18—N8173.7 (3)
C9—C17—N7—C18115.3 (3)C17—C9—O5—C21157.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N7—H7···O40.79 (3)2.02 (3)2.694 (3)143 (3)
N8—H8···O3i0.81 (3)2.01 (3)2.823 (3)179 (3)
Symmetry code: (i) x+1, y+2, z.
(II) top
Crystal data top
C14H14Cl2N2O4Dx = 1.445 Mg m3
Mr = 345.18Melting point: 392 K
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 11.409 (2) ÅCell parameters from 22 reflections
b = 4.595 (2) Åθ = 10.4–14.5°
c = 15.667 (1) ŵ = 0.43 mm1
β = 105.079 (9)°T = 298 K
V = 793.1 (3) Å3Needle, colourless
Z = 20.70 × 0.02 × 0.01 mm
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.029
ω scansθmax = 27.5°, θmin = 2.5°
Absorption correction: integration
(Coppens et al., 1965)
h = 015
Tmin = 0.956, Tmax = 0.991k = 60
2130 measured reflectionsl = 2020
2031 independent reflections3 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) = 0.126Δρmax = 0.24 e Å3
S = 0.97Δρmin = 0.24 e Å3
2031 reflectionsAbsolute structure: Flack (1983)
208 parametersAbsolute 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
xyzUiso*/Ueq
Cl10.8787 (1)0.2517 (5)0.0263 (1)0.0793 (7)
Cl21.2476 (2)0.8432 (8)0.2536 (1)0.129 (1)
O30.5315 (4)0.601 (1)0.0979 (2)0.079 (2)
O40.8493 (4)0.142 (1)0.1132 (3)0.067 (2)
O50.9233 (4)0.701 (1)0.2743 (2)0.066 (1)
O61.0494 (4)1.067 (1)0.3267 (4)0.086 (2)
N70.7191 (4)0.507 (1)0.1864 (3)0.051 (2)
N80.6554 (4)0.294 (2)0.0483 (3)0.055 (2)
C90.8306 (5)0.821 (2)0.3107 (4)0.059 (2)
C100.8519 (6)0.733 (3)0.4082 (4)0.095 (3)
C110.7438 (6)0.546 (2)0.4114 (4)0.064 (2)
C120.7188 (7)0.411 (2)0.4832 (4)0.086 (3)
C130.6164 (8)0.244 (3)0.4725 (5)0.099 (3)
C140.5370 (6)0.225 (3)0.3902 (6)0.103 (3)
C150.5595 (7)0.362 (2)0.3181 (4)0.080 (3)
C160.6638 (6)0.522 (2)0.3286 (4)0.060 (2)
C170.7075 (5)0.688 (2)0.2590 (4)0.054 (2)
C180.6303 (6)0.476 (2)0.1124 (4)0.052 (2)
C190.7592 (6)0.139 (2)0.0516 (4)0.053 (2)
C200.7527 (6)0.030 (2)0.0331 (4)0.068 (2)
C211.0263 (6)0.853 (2)0.2851 (5)0.063 (2)
C221.1012 (6)0.711 (3)0.2308 (5)0.101 (3)
H70.789 (5)0.36 (2)0.182 (4)0.0786 (3)*
H80.594 (5)0.28 (2)0.007 (4)0.0791 (3)*
H90.82871.04040.30530.0709*
H10A0.85580.91480.44430.1125*
H10B0.92500.63920.42740.1125*
H120.77270.44700.54030.1036*
H130.60030.15880.52140.1167*
H140.46450.13000.38310.1216*
H150.50350.35930.26150.0961*
H170.65240.85650.23680.0661*
H20A0.68210.13390.04530.0816*
H20B0.74700.11980.07980.0816*
H22A1.06280.75830.16990.1218*
H22B1.10420.52220.24220.1218*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.066 (1)0.089 (2)0.084 (1)0.002 (1)0.0206 (9)0.015 (1)
Cl20.062 (1)0.229 (4)0.094 (1)0.029 (2)0.0181 (10)0.025 (2)
O30.045 (2)0.136 (6)0.046 (2)0.020 (3)0.003 (2)0.002 (3)
O40.050 (2)0.098 (5)0.046 (2)0.008 (3)0.003 (2)0.005 (3)
O50.047 (2)0.080 (4)0.061 (3)0.001 (3)0.000 (2)0.013 (3)
O60.074 (3)0.086 (5)0.094 (4)0.026 (3)0.013 (3)0.033 (4)
N70.043 (3)0.068 (4)0.034 (3)0.003 (3)0.004 (2)0.013 (3)
N80.033 (3)0.091 (6)0.034 (3)0.000 (4)0.002 (2)0.004 (4)
C90.051 (4)0.069 (7)0.051 (4)0.003 (4)0.001 (3)0.001 (4)
C100.072 (4)0.155 (9)0.049 (4)0.029 (7)0.001 (3)0.002 (6)
C110.061 (4)0.084 (6)0.041 (4)0.011 (5)0.006 (3)0.003 (4)
C120.086 (5)0.133 (9)0.040 (4)0.002 (6)0.015 (4)0.001 (5)
C130.107 (6)0.126 (8)0.072 (5)0.017 (8)0.040 (5)0.009 (7)
C140.082 (5)0.151 (10)0.086 (6)0.033 (8)0.041 (5)0.032 (8)
C150.073 (5)0.110 (8)0.062 (5)0.013 (6)0.025 (4)0.028 (5)
C160.051 (4)0.074 (6)0.054 (4)0.007 (4)0.014 (3)0.014 (4)
C170.047 (3)0.062 (6)0.045 (4)0.008 (4)0.000 (3)0.003 (4)
C180.049 (4)0.070 (6)0.033 (3)0.008 (4)0.004 (3)0.005 (4)
C190.046 (4)0.072 (6)0.041 (4)0.017 (4)0.008 (3)0.002 (4)
C200.066 (4)0.087 (7)0.048 (4)0.003 (5)0.007 (3)0.002 (5)
C210.053 (4)0.070 (7)0.056 (4)0.013 (5)0.003 (4)0.006 (5)
C220.061 (4)0.150 (10)0.094 (5)0.026 (7)0.024 (4)0.048 (7)
Geometric parameters (Å, º) top
Cl1—C201.741 (8)C11—C121.38 (1)
Cl2—C221.726 (8)C11—C161.383 (8)
O3—C181.231 (8)C12—C131.37 (1)
O4—C191.214 (6)C12—H120.959
O5—C91.435 (8)C13—C141.37 (1)
O5—C211.339 (9)C13—H130.920
O6—C211.17 (1)C14—C151.37 (1)
N7—C171.441 (9)C14—H140.917
N7—C181.333 (7)C15—C161.37 (1)
N7—H71.05 (7)C15—H150.949
N8—C181.394 (10)C16—C171.52 (1)
N8—C191.371 (9)C17—H171.002
N8—H80.82 (5)C19—C201.522 (10)
C9—C101.537 (9)C20—H20A0.912
C9—C171.552 (8)C20—H20B0.996
C9—H91.013C21—C221.50 (1)
C10—C111.51 (1)C22—H22A0.966
C10—H10A1.005C22—H22B0.883
C10—H10B0.917
C9—O5—C21117.6 (6)C14—C15—H15122.6
C17—N7—C18122.9 (6)C16—C15—H15118.1
C17—N7—H7130 (3)C11—C16—C15119.8 (7)
C18—N7—H7107 (3)C11—C16—C17111.9 (6)
C18—N8—C19128.6 (5)C15—C16—C17128.3 (5)
C18—N8—H8109 (5)N7—C17—C9112.5 (5)
C19—N8—H8123 (5)N7—C17—C16113.1 (6)
O5—C9—C10110.6 (5)N7—C17—H17110.5
O5—C9—C17107.6 (5)C9—C17—C16104.1 (5)
O5—C9—H9110.5C9—C17—H17106.2
C10—C9—C17107.7 (6)C16—C17—H17110.1
C10—C9—H9109.9O3—C18—N7124.2 (6)
C17—C9—H9110.6O3—C18—N8119.8 (5)
C9—C10—C11105.2 (5)N7—C18—N8116.0 (6)
C9—C10—H10A108.2O4—C19—N8124.6 (6)
C9—C10—H10B110.1O4—C19—C20122.6 (6)
C11—C10—H10A111.7N8—C19—C20112.8 (5)
C11—C10—H10B113.8Cl1—C20—C19113.2 (4)
H10A—C10—H10B107.6Cl1—C20—H20A112.3
C10—C11—C12128.8 (5)Cl1—C20—H20B110.2
C10—C11—C16111.1 (6)C19—C20—H20A106.8
C12—C11—C16120.1 (7)C19—C20—H20B105.4
C11—C12—C13120.2 (6)H20A—C20—H20B108.7
C11—C12—H12117.6O5—C21—O6124.8 (7)
C13—C12—H12122.1O5—C21—C22108.1 (7)
C12—C13—C14119.0 (9)O6—C21—C22127.0 (8)
C12—C13—H13118.9Cl2—C22—C21113.1 (7)
C14—C13—H13122.0Cl2—C22—H22A106.8
C13—C14—C15121.7 (9)Cl2—C22—H22B108.6
C13—C14—H14119.9C21—C22—H22A106.4
C15—C14—H14118.3C21—C22—H22B108.1
C14—C15—C16119.2 (6)H22A—C22—H22B113.9
C9—O5—C21—C22171.7 (6)C17—N7—C18—N8180.0 (7)
C9—C17—N7—C18149.4 (7)C17—C9—O5—C21156.6 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N7—H7···O41.05 (7)1.75 (7)2.688 (8)146 (4)
N8—H8···O3i0.82 (5)2.05 (6)2.837 (6)159 (8)
Symmetry code: (i) x+1, y1/2, z.
 

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