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In the crystals of trans-4-methylcinnamamide, C10H11NO (I), trans-4-chlorocinnamamide, C9H8ClNO (II), trans-3-(2-thienyl)acrylamide, C7H7NOS (III), and trans-cinnamamide, C9H9NO (IV), the shortest intermolecular C...C distances between the C=C double bonds are 3.670 (2), 3.632 (2), 3.762 (3) and 4.120 (2) Å, respectively, for the pair of molecules related by a center of symmetry. The structure analysis was also carried out for trans-2-(p-chlorophenyl)-cis-4-(p-chlorophenyl)-1-trans-3-diamidocyclobutane, C18H16Cl2­N2O2 (V), which is the α-type photodimer of (II). The N—H...O hydrogen-bond networks in (I)–(III) are composed of two-dimensional pleated sheets, and those in (IV) and (V) of one-dimensional flat ribbons. The single crystals of (I), (II) and (IV) were photoirradiated with a 250 W ultra-high-pressure mercury lamp through a band-pass filter or a long-pass filter for 2–5 h. The photodimer was produced in each crystal with retention of the single-crystal form. The populations of the dimers were converged to 86.2 (4), 48.4 (6) and 4.5 (2)% in the refinement of the crystals after photoirradiation, (I^{\prime}), (II^{\prime}) and (IV^{\prime}), respectively. Although the intermolecular N—H...O hydrogen-bond network remained in (I^{\prime}) and (II^{\prime}), the network was partly broken in (IV^{\prime}) in the process of photoreaction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768100002329/oa0024sup1.cif
Contains datablocks amide, I, I', II, II', III, IV, IV', V

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100002329/oa0024Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100002329/oa0024I'sup3.hkl
Contains datablock I'

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100002329/oa0024IIsup4.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100002329/oa0024II'sup5.hkl
Contains datablock II'

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100002329/oa0024IIIsup6.hkl
Contains datablock III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100002329/oa0024IVsup7.hkl
Contains datablock IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100002329/oa0024IV'sup8.hkl
Contains datablock IV'

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100002329/oa0024Vsup9.hkl
Contains datablock V

CCDC references: 148910; 148911; 148912; 148913; 148914; 148915; 148916; 148917

Computing details top

For all 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, 1998); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-II (Johnson, 1976); software used to prepare material for publication: TEXSAN.

(I) top
Crystal data top
C10H11NOZ = 8
Mr = 161.20Dx = 1.209 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 25 reflections
a = 23.599 (3) Åθ = 13.2–15.0°
b = 9.148 (3) ŵ = 0.08 mm1
c = 8.208 (3) ÅT = 298 K
β = 87.69 (2)°Plate-like, colourless
V = 1770.5 (8) Å30.8 × 0.5 × 0.2 mm
Data collection top
Rigaku AFC7R
diffractometer
θmax = 27.5°, θmin = 2.5°
θ–2θ scansh = 031
2080 measured reflectionsk = 120
2034 independent reflectionsl = 1111
1420 reflections with I > 2σ(I)3 standard reflections every 150 reflections
Rint = 0.030 intensity decay: none
Refinement top
Refinement on F2All H-atom parameters refined
R[F2 > 2σ(F2)] = 0.038 w = 1/[σ2(Fo2) + (0.052P)2 + 0.6818P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.116(Δ/σ)max = 0.0001
S = 1.03Δρmax = 0.16 e Å3
2034 reflectionsΔρmin = 0.16 e Å3
165 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*/UeqOcc. (<1)
O10.28647 (5)0.6568 (1)0.1656 (1)0.0589 (3)
N20.25085 (6)0.8849 (1)0.1677 (2)0.0523 (3)
C30.28094 (6)0.7779 (1)0.2318 (2)0.0434 (3)
C40.30864 (6)0.8131 (2)0.3862 (2)0.0454 (3)
C50.33932 (6)0.7144 (2)0.4615 (2)0.0463 (3)
C60.37090 (6)0.7337 (2)0.6105 (2)0.0442 (3)
C70.37877 (7)0.8691 (2)0.6831 (2)0.0513 (4)
C80.41025 (7)0.8816 (2)0.8210 (2)0.0564 (4)
C90.43477 (6)0.7602 (2)0.8916 (2)0.0534 (4)
C100.42683 (7)0.6257 (2)0.8195 (2)0.0556 (4)
C110.39536 (7)0.6118 (2)0.6812 (2)0.0516 (4)
C120.4694 (1)0.7748 (3)1.0417 (3)0.0745 (6)
H2A0.2341 (7)0.868 (2)0.066 (2)0.07000 (6)*
H2B0.2434 (7)0.971 (2)0.224 (2)0.07516 (7)*
H40.3039 (6)0.912 (2)0.424 (2)0.05154 (5)*
H50.3412 (6)0.616 (2)0.416 (2)0.05081 (5)*
H70.3628 (7)0.958 (2)0.635 (2)0.06280 (6)*
H80.4155 (7)0.980 (2)0.865 (2)0.07000 (6)*
H100.4442 (7)0.537 (2)0.863 (2)0.06353 (6)*
H110.3902 (7)0.516 (2)0.633 (2)0.06900 (6)*
H12A0.491 (2)0.680 (4)1.063 (4)0.0534 (1)*0.50
H12B0.439 (1)0.778 (5)1.135 (5)0.0573 (1)*0.50
H12C0.488 (2)0.873 (5)1.045 (5)0.0673 (1)*0.50
H12*A0.458 (2)0.870 (5)1.107 (5)0.0748 (1)*0.50
H12*B0.514 (2)0.771 (5)1.011 (5)0.0862 (2)*0.50
H12*C0.457 (2)0.699 (5)1.123 (6)0.0856 (2)*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0886 (8)0.0380 (5)0.0520 (6)0.0056 (5)0.0269 (5)0.0031 (4)
N20.0692 (8)0.0396 (6)0.0497 (7)0.0046 (6)0.0216 (6)0.0021 (5)
C30.0530 (8)0.0366 (6)0.0414 (7)0.0046 (6)0.0103 (6)0.0025 (5)
C40.0537 (8)0.0414 (7)0.0417 (7)0.0020 (6)0.0092 (6)0.0026 (6)
C50.0537 (8)0.0438 (7)0.0420 (7)0.0012 (6)0.0099 (6)0.0011 (6)
C60.0448 (7)0.0497 (7)0.0385 (7)0.0000 (6)0.0054 (6)0.0014 (6)
C70.0588 (9)0.0509 (8)0.0449 (7)0.0063 (7)0.0122 (6)0.0012 (6)
C80.0641 (10)0.0580 (9)0.0482 (8)0.0016 (7)0.0143 (7)0.0088 (7)
C90.0496 (8)0.0690 (10)0.0424 (7)0.0015 (7)0.0102 (6)0.0012 (7)
C100.0582 (9)0.0599 (9)0.0494 (8)0.0060 (7)0.0125 (7)0.0087 (7)
C110.0594 (9)0.0482 (8)0.0479 (8)0.0011 (7)0.0096 (6)0.0019 (6)
C120.078 (1)0.089 (2)0.059 (1)0.004 (1)0.031 (1)0.002 (1)
Geometric parameters (Å, º) top
O1—C31.239 (2)C8—C91.390 (2)
N2—C31.330 (2)C8—H80.98 (2)
N2—H2A0.95 (2)C9—C101.381 (2)
N2—H2B0.92 (2)C9—C121.512 (3)
C3—C41.484 (2)C10—C111.387 (2)
C4—C51.325 (2)C10—H100.98 (2)
C4—H40.96 (2)C11—H110.97 (2)
C5—C61.469 (2)C12—H12A1.02 (4)
C5—H50.97 (2)C12—H12B1.02 (4)
C6—C71.390 (2)C12—H12C1.00 (4)
C6—C111.392 (2)C12—H12*A1.06 (4)
C7—C81.383 (2)C12—H12*B1.07 (5)
C7—H70.99 (2)C12—H12*C1.00 (5)
C3—N2—H2A118.5 (10)C8—C9—C10117.9 (1)
C3—N2—H2B121.3 (11)C8—C9—C12121.1 (2)
H2A—N2—H2B119.9 (15)C10—C9—C12121.0 (2)
O1—C3—N2122.2 (1)C9—C10—C11121.2 (1)
O1—C3—C4121.8 (1)C9—C10—H10121.1 (10)
N2—C3—C4116.0 (1)C11—C10—H10117.7 (10)
C3—C4—C5121.2 (1)C6—C11—C10120.8 (1)
C3—C4—H4115.6 (9)C6—C11—H11119.7 (10)
C5—C4—H4123.2 (9)C10—C11—H11119.5 (10)
C4—C5—C6127.7 (1)C9—C12—H12A111 (2)
C4—C5—H5118.0 (9)C9—C12—H12B103 (2)
C6—C5—H5114.3 (9)C9—C12—H12C111 (2)
C5—C6—C7123.0 (1)C9—C12—H12*A110 (3)
C5—C6—C11118.9 (1)C9—C12—H12*B111 (2)
C7—C6—C11118.0 (1)C9—C12—H12*C109 (3)
C6—C7—C8120.7 (1)H12A—C12—H12B103 (3)
C6—C7—H7120.3 (10)H12A—C12—H12C123 (3)
C8—C7—H7119.0 (10)H12B—C12—H12C104 (3)
C7—C8—C9121.4 (1)H12*A—C12—H12*B113 (4)
C7—C8—H8117.5 (10)H12*A—C12—H12*C100 (4)
C9—C8—H8121.1 (10)H12*B—C12—H12*C113 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.95 (2)1.99 (2)2.932 (2)169.1 (15)
N2—H2B···O1ii0.92 (2)2.04 (2)2.956 (2)170.4 (16)
Symmetry codes: (i) x+1/2, y+3/2, z; (ii) x+1/2, y+1/2, z+1/2.
(I') top
Crystal data top
C10H11NOZ = 8
Mr = 161.20Dx = 1.160 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 25 reflections
a = 22.444 (1) Åθ = 12.0–14.6°
b = 9.557 (2) ŵ = 0.08 mm1
c = 8.632 (1) ÅT = 298 K
β = 94.50 (1)°Plate-like, colourless
V = 1845.9 (5) Å30.7 × 0.4 × 0.2 mm
Data collection top
Rigaku AFC7R
diffractometer
θmax = 27.5°, θmin = 2.5°
θ–2θ scansh = 029
2404 measured reflectionsk = 125
2128 independent reflectionsl = 1111
1294 reflections with I > 2σ(I)3 standard reflections every 150 reflections
Rint = 0.017 intensity decay: none
Refinement top
Refinement on F2H atoms riding
R[F2 > 2σ(F2)] = 0.062 w = 1/[σ2(Fo2) + (0.0648P)2 + 2.4674P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.212(Δ/σ)max = 0.0001
S = 1.19Δρmax = 0.30 e Å3
2128 reflectionsΔρmin = 0.22 e Å3
110 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*/UeqOcc. (<1)
O10.28650.65670.16570.0574*0.138 (4)
O1*0.2713 (1)0.6544 (2)0.1924 (2)0.0493 (7)0.862 (4)
N20.25070.88450.16790.0506*0.138 (4)
N2*0.2574 (2)0.8828 (2)0.1439 (3)0.0535 (8)0.862 (4)
C30.28090.77820.23210.0424*0.138 (4)
C3*0.2672 (1)0.7753 (3)0.2392 (3)0.0382 (7)0.862 (4)
C40.30860.81290.38620.0443*0.138 (4)
C4*0.2701 (1)0.8123 (3)0.4104 (3)0.0391 (8)0.862 (4)
C50.33940.71440.46140.0450*0.138 (4)
C5*0.2940 (1)0.6959 (3)0.5221 (3)0.0384 (7)0.862 (4)
C60.37090.73370.61050.0436*0.138 (4)
C6*0.3472 (2)0.7218 (3)0.6381 (3)0.0429 (8)0.862 (4)
C70.37880.86930.68290.0502*0.138 (4)
C7*0.3657 (2)0.8512 (3)0.6893 (4)0.061 (1)0.862 (4)
C80.41030.88190.82110.0554*0.138 (4)
C8*0.4099 (2)0.8659 (4)0.8100 (6)0.083 (1)0.862 (4)
C90.43480.76060.89160.0529*0.138 (4)
C9*0.4379 (2)0.7538 (6)0.8820 (5)0.081 (1)0.862 (4)
C100.42690.62530.81950.0547*0.138 (4)
C10*0.4200 (2)0.6247 (5)0.8307 (5)0.080 (1)0.862 (4)
C110.39540.61150.68110.0506*0.138 (4)
C11*0.3761 (2)0.6082 (3)0.7094 (4)0.0593 (10)0.862 (4)
C120.46960.77451.04140.0750*0.138 (4)
C12*0.4859 (2)0.7711 (4)1.0137 (5)0.128 (3)0.862 (4)
H2A0.23040.87470.06640.0607*0.138 (4)
H2B0.24900.97160.22270.0607*0.138 (4)
H2*A0.25500.86910.03450.0623*0.862 (4)
H2*B0.25340.97470.18460.0623*0.862 (4)
H40.30440.90420.43050.0532*0.138 (4)
H4*0.28960.90220.43190.0441*0.862 (4)
H50.34090.62390.41370.0540*0.138 (4)
H5*0.30060.61220.46420.0432*0.862 (4)
H70.36150.95070.63210.0603*0.138 (4)
H7*0.34760.93260.64170.0714*0.862 (4)
H80.41590.97160.87020.0664*0.138 (4)
H8*0.42110.95750.84530.0986*0.862 (4)
H100.44430.54410.87060.0657*0.138 (4)
H10*0.43770.54310.87960.0938*0.862 (4)
H110.38980.52170.63230.0607*0.138 (4)
H11*0.36550.51600.67370.0684*0.862 (4)
H12A0.48340.68401.07640.0901*0.138 (4)
H12B0.50330.83451.03000.0901*0.138 (4)
H12C0.44490.81411.11610.0901*0.138 (4)
H12*A0.52210.72840.98730.1498*0.862 (4)
H12*B0.47340.72791.10520.1498*0.862 (4)
H12*C0.49300.86791.03360.1498*0.862 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1*0.088 (2)0.035 (1)0.0240 (9)0.003 (1)0.000 (1)0.0004 (8)
N2*0.098 (2)0.037 (1)0.024 (1)0.001 (1)0.003 (1)0.003 (1)
C3*0.050 (2)0.038 (1)0.026 (1)0.009 (1)0.001 (1)0.004 (1)
C4*0.058 (2)0.032 (1)0.026 (1)0.006 (1)0.005 (1)0.000 (1)
C5*0.056 (2)0.033 (1)0.025 (1)0.001 (1)0.006 (1)0.001 (1)
C6*0.052 (2)0.047 (2)0.029 (1)0.001 (1)0.001 (1)0.001 (1)
C7*0.067 (2)0.050 (2)0.062 (2)0.002 (2)0.019 (2)0.006 (2)
C8*0.080 (3)0.076 (3)0.086 (3)0.006 (2)0.032 (2)0.026 (2)
C9*0.060 (3)0.114 (4)0.064 (2)0.002 (3)0.026 (2)0.000 (3)
C10*0.072 (3)0.090 (3)0.073 (3)0.008 (2)0.022 (2)0.028 (2)
C11*0.066 (2)0.057 (2)0.053 (2)0.001 (2)0.008 (2)0.009 (2)
C12*0.086 (4)0.185 (7)0.102 (4)0.006 (4)0.058 (3)0.006 (4)
Geometric parameters (Å, º) top
O1—C31.305C7—H70.96
O1*—C3*1.229 (4)C7*—C8*1.390 (6)
N2—C31.319C7*—H7*0.96
N2—H2A0.96C8—C91.401
N2—H2B0.96C8—H80.96
N2*—C3*1.324 (4)C8*—C9*1.366 (7)
N2*—H2*A0.95C8*—H8*0.95
N2*—H2*B0.95C9—C101.440
C3—C41.462C9—C121.463
C3*—C4*1.516 (4)C9*—C10*1.361 (7)
C4—C51.310C9*—C12*1.513 (6)
C4—H40.96C10—C111.346
C4*—C5*1.540 (4)C10—H100.96
C4*—C5*i1.595 (4)C10*—C11*1.389 (6)
C4*—H4*0.98C10*—H10*0.96
C5—C61.431C11—H110.96
C5—H50.96C11*—H11*0.96
C5*—C6*1.517 (4)C12—H12A0.96
C5*—H5*0.96C12—H12B0.96
C6—C71.444C12—H12C0.96
C6—C111.409C12*—H12*A0.95
C6*—C7*1.367 (5)C12*—H12*B0.95
C6*—C11*1.385 (4)C12*—H12*C0.95
C7—C81.344
C3—N2—H2A120C6*—C7*—C8*121.0 (3)
C3—N2—H2B120C6*—C7*—H7*119
H2A—N2—H2B120C8*—C7*—H7*120
C3*—N2*—H2*A120C7—C8—C9118.2
C3*—N2*—H2*B120C7—C8—H8121
H2*A—N2*—H2*B120C9—C8—H8121
O1—C3—N2124.4C7*—C8*—C9*122.5 (4)
O1—C3—C4123.6C7*—C8*—H8*119
N2—C3—C4112.1C9*—C8*—H8*118
O1*—C3*—N2*122.6 (2)C8—C9—C10121.6
O1*—C3*—C4*122.7 (2)C8—C9—C12118.2
N2*—C3*—C4*114.6 (2)C10—C9—C12120.2
C3—C4—C5117.3C8*—C9*—C10*116.7 (4)
C3—C4—H4121C8*—C9*—C12*122.1 (4)
C5—C4—H4121C10*—C9*—C12*121.2 (4)
C3*—C4*—C5*115.3 (2)C9—C10—C11120.7
C3*—C4*—C5*i112.0 (2)C9—C10—H10120
C3*—C4*—H4*112C11—C10—H10120
C5*—C4*—C5*i90.9 (2)C9*—C10*—C11*121.5 (4)
C5*—C4*—H4*113C9*—C10*—H10*120
C5*i—C4*—H4*112C11*—C10*—H10*119
C4—C5—C6123.9C6—C11—C10117.6
C4—C5—H5118C6—C11—H11121
C6—C5—H5118C10—C11—H11121
C4*—C5*—C4*i89.1 (2)C6*—C11*—C10*121.7 (3)
C4*—C5*—C6*120.8 (2)C6*—C11*—H11*120
C4*—C5*—H5*110C10*—C11*—H11*119
C4*i—C5*—C6*116.9 (2)C9—C12—H12A110
C4*i—C5*—H5*109C9—C12—H12B110
C6*—C5*—H5*110C9—C12—H12C109
C5—C6—C7122.7H12A—C12—H12B110
C5—C6—C11115.5H12A—C12—H12C109
C7—C6—C11121.8H12B—C12—H12C110
C5*—C6*—C7*124.4 (3)C9*—C12*—H12*A110
C5*—C6*—C11*118.9 (3)C9*—C12*—H12*B110
C7*—C6*—C11*116.5 (3)C9*—C12*—H12*C110
C6—C7—C8120.2H12*A—C12*—H12*B109
C6—C7—H7120H12*A—C12*—H12*C109
C8—C7—H7120H12*B—C12*—H12*C109
Symmetry code: (i) x+1/2, y+3/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1ii0.962.032.961162
N2—H2B···O1iii0.962.193.117161
N2*—H2*A···O1*ii0.952.012.946 (3)166
N2*—H2*B···O1*iii0.952.123.049 (3)166
Symmetry codes: (ii) x+1/2, y+3/2, z; (iii) x+1/2, y+1/2, z+1/2.
(II) top
Crystal data top
C9H8ClNOZ = 4
Mr = 181.62Dx = 1.404 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 11.037 (1) Åθ = 12.2–14.8°
b = 9.075 (2) ŵ = 0.39 mm1
c = 9.042 (2) ÅT = 298 K
β = 108.42 (1)°Plate-like, colourless
V = 859.3 (2) Å30.6 × 0.6 × 0.1 mm
Data collection top
Rigaku AFC7R
diffractometer
Rint = 0.015
θ–2θ scansθmax = 27.5°, θmin = 2.5°
Absorption correction: integration
(Coppens et al., 1965)
h = 1414
Tmin = 0.799, Tmax = 0.961k = 012
2101 measured reflectionsl = 120
1977 independent reflections3 standard reflections every 150 reflections
1360 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2All H-atom parameters refined
R[F2 > 2σ(F2)] = 0.038 w = 1/[σ2(Fo2) + (0.0518P)2 + 0.3386P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.115(Δ/σ)max = 0.0001
S = 1.02Δρmax = 0.27 e Å3
1977 reflectionsΔρmin = 0.21 e Å3
141 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
Cl10.93953 (7)0.02271 (7)0.14460 (7)0.0704 (2)
O20.5741 (2)0.0971 (2)0.8706 (2)0.0534 (4)
N30.4869 (2)0.1302 (2)0.8370 (2)0.0488 (4)
C40.5552 (2)0.0230 (2)0.8019 (2)0.0410 (4)
C50.6096 (2)0.0568 (2)0.6750 (2)0.0423 (4)
C60.6905 (2)0.0348 (2)0.6409 (2)0.0425 (4)
C70.7533 (2)0.0155 (2)0.5210 (2)0.0401 (4)
C80.7562 (2)0.1189 (2)0.4470 (2)0.0471 (5)
C90.8138 (2)0.1314 (2)0.3330 (2)0.0510 (5)
C100.8694 (2)0.0085 (2)0.2913 (2)0.0447 (4)
C110.8706 (2)0.1247 (2)0.3635 (2)0.0475 (5)
C120.8127 (2)0.1361 (2)0.4775 (2)0.0458 (4)
H3A0.453 (2)0.112 (2)0.911 (2)0.04934 (7)*
H3B0.469 (2)0.209 (3)0.780 (3)0.05813 (8)*
H50.583 (2)0.148 (2)0.618 (2)0.04806 (7)*
H60.713 (2)0.125 (3)0.697 (3)0.05497 (8)*
H80.720 (2)0.203 (3)0.475 (3)0.06668 (9)*
H90.820 (2)0.223 (3)0.284 (2)0.05567 (8)*
H110.908 (2)0.209 (3)0.334 (3)0.06794 (9)*
H120.810 (2)0.231 (2)0.528 (2)0.05114 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0959 (5)0.0668 (4)0.0691 (4)0.0169 (3)0.0557 (4)0.0111 (3)
O20.077 (1)0.0363 (7)0.0594 (9)0.0067 (7)0.0394 (8)0.0056 (6)
N30.064 (1)0.0369 (9)0.055 (1)0.0047 (8)0.0333 (9)0.0024 (8)
C40.0457 (10)0.0365 (9)0.0433 (9)0.0043 (8)0.0176 (8)0.0046 (8)
C50.050 (1)0.0381 (10)0.0416 (10)0.0008 (8)0.0187 (9)0.0019 (8)
C60.050 (1)0.0374 (10)0.0422 (9)0.0006 (8)0.0179 (8)0.0028 (8)
C70.0425 (10)0.0388 (9)0.0400 (9)0.0016 (8)0.0144 (8)0.0006 (8)
C80.058 (1)0.0368 (10)0.051 (1)0.0068 (9)0.0241 (10)0.0021 (8)
C90.067 (1)0.040 (1)0.052 (1)0.0012 (9)0.027 (1)0.0065 (9)
C100.050 (1)0.048 (1)0.0421 (9)0.0062 (9)0.0227 (8)0.0057 (8)
C110.054 (1)0.041 (1)0.051 (1)0.0030 (9)0.0223 (10)0.0058 (9)
C120.056 (1)0.0348 (10)0.051 (1)0.0053 (8)0.0219 (9)0.0037 (8)
Geometric parameters (Å, º) top
Cl1—C101.739 (2)C7—C81.396 (3)
O2—C41.240 (2)C7—C121.394 (3)
N3—C41.329 (3)C8—C91.377 (4)
N3—H3A0.88 (3)C8—H80.94 (3)
N3—H3B0.87 (2)C9—C101.382 (3)
C4—C51.486 (3)C9—H90.95 (2)
C5—C61.326 (3)C10—C111.372 (3)
C5—H50.97 (2)C11—C121.378 (4)
C6—C71.470 (3)C11—H110.94 (3)
C6—H60.95 (2)C12—H120.98 (2)
C4—N3—H3A117 (1)C7—C8—C9121.1 (2)
C4—N3—H3B120 (2)C7—C8—H8121 (2)
H3A—N3—H3B123 (2)C9—C8—H8118 (2)
O2—C4—N3122.8 (2)C8—C9—C10119.2 (2)
O2—C4—C5121.6 (2)C8—C9—H9122 (2)
N3—C4—C5115.6 (2)C10—C9—H9119 (2)
C4—C5—C6121.1 (2)Cl1—C10—C9119.4 (2)
C4—C5—H5117 (1)Cl1—C10—C11119.2 (2)
C6—C5—H5121 (1)C9—C10—C11121.4 (2)
C5—C6—C7127.3 (2)C10—C11—C12119.0 (2)
C5—C6—H6120 (2)C10—C11—H11121 (2)
C7—C6—H6113 (2)C12—C11—H11120 (2)
C6—C7—C8123.0 (2)C7—C12—C11121.5 (2)
C6—C7—C12119.2 (2)C7—C12—H12118 (1)
C8—C7—C12117.8 (2)C11—C12—H12120 (1)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O2i0.88 (3)2.09 (2)2.941 (3)163 (2)
N3—H3B···O2ii0.87 (2)2.18 (2)3.050 (2)178 (2)
Symmetry codes: (i) x+1, y, z+2; (ii) x+1, y+1/2, z+3/2.
(II') top
Crystal data top
C9H8ClNOZ = 4
Mr = 181.62Dx = 1.379 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 11.398 (3) Åθ = 10.7–14.8°
b = 9.330 (4) ŵ = 0.38 mm1
c = 8.698 (3) ÅT = 298 K
β = 108.95 (2)°Plate-like, colourless
V = 874.8 (5) Å30.6 × 0.6 × 0.1 mm
Data collection top
Rigaku AFC7R
diffractometer
Rint = 0.026
ω scansθmax = 27.5°, θmin = 2.5°
Absorption correction: integration
(Coppens et al., 1965)
h = 1414
Tmin = 0.812, Tmax = 0.962k = 012
2138 measured reflectionsl = 120
2006 independent reflections3 standard reflections every 150 reflections
1148 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2H atoms riding
R[F2 > 2σ(F2)] = 0.049 w = 1/[σ2(Fo2) + (0.0526P)2 + 0.2095P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.145(Δ/σ)max = 0.0001
S = 1.11Δρmax = 0.15 e Å3
2006 reflectionsΔρmin = 0.14 e Å3
218 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*/UeqOcc. (<1)
Cl10.9389 (6)0.0251 (6)0.1346 (6)0.105 (2)0.516 (6)
Cl1*0.9768 (5)0.0172 (8)0.1967 (7)0.114 (2)0.484 (6)
O20.545 (1)0.089 (1)0.831 (1)0.055 (2)0.516 (6)
O2*0.580 (2)0.101 (2)0.874 (2)0.072 (3)0.484 (6)
N30.511 (1)0.1298 (5)0.859 (1)0.077 (3)0.516 (6)
N3*0.4989 (7)0.1395 (6)0.8377 (7)0.070 (4)0.484 (6)
C40.548 (1)0.027 (2)0.793 (1)0.066 (6)0.516 (6)
C4*0.551 (1)0.026 (1)0.790 (2)0.063 (6)0.484 (6)
C50.6165 (7)0.0586 (4)0.6765 (7)0.054 (1)0.516 (6)
C5*0.5415 (7)0.0651 (5)0.6105 (8)0.056 (2)0.484 (6)
C60.6908 (5)0.0347 (4)0.6373 (6)0.059 (2)0.516 (6)
C6*0.5906 (5)0.0544 (4)0.5241 (6)0.054 (2)0.484 (6)
C70.7531 (7)0.0158 (9)0.5191 (8)0.052 (2)0.516 (6)
C7*0.7013 (8)0.029 (1)0.4628 (9)0.053 (2)0.484 (6)
C80.766 (2)0.101 (1)0.457 (2)0.070 (4)0.516 (6)
C8*0.739 (2)0.1194 (9)0.428 (2)0.052 (3)0.484 (6)
C90.822 (2)0.1216 (9)0.346 (3)0.087 (7)0.516 (6)
C9*0.824 (2)0.1288 (8)0.340 (2)0.065 (6)0.484 (6)
C100.859 (2)0.004 (3)0.278 (2)0.054 (3)0.516 (6)
C10*0.889 (2)0.007 (4)0.316 (2)0.060 (4)0.484 (6)
C110.846 (2)0.119 (2)0.327 (2)0.073 (4)0.516 (6)
C11*0.862 (2)0.134 (2)0.367 (2)0.060 (3)0.484 (6)
C120.803 (2)0.131 (1)0.468 (2)0.075 (3)0.516 (6)
C12*0.763 (2)0.1493 (9)0.426 (2)0.074 (4)0.484 (6)
H3A0.46640.11150.93380.1013*0.516 (6)
H3B0.53730.22480.84540.1013*0.516 (6)
H3*A0.49440.14060.94600.0760*0.484 (6)
H3*B0.46530.21720.76480.0760*0.484 (6)
H50.61460.15560.63830.0620*0.516 (6)
H5*0.58260.15400.60680.0710*0.484 (6)
H60.70180.12630.68980.0627*0.516 (6)
H6*0.60450.14020.58780.0685*0.484 (6)
H80.73630.18660.49400.0679*0.516 (6)
H8*0.70320.20180.46210.0579*0.484 (6)
H90.84990.21800.33970.1231*0.516 (6)
H9*0.83530.21840.29300.0650*0.484 (6)
H110.86910.20720.28550.0759*0.516 (6)
H11*0.91500.21410.36700.1080*0.484 (6)
H120.80910.21940.52630.0882*0.516 (6)
H12*0.73820.24400.44600.0846*0.484 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.143 (4)0.104 (2)0.110 (3)0.014 (2)0.097 (3)0.007 (2)
Cl1*0.100 (3)0.153 (3)0.123 (4)0.012 (2)0.085 (3)0.005 (3)
O20.088 (7)0.044 (3)0.043 (4)0.005 (4)0.035 (4)0.004 (3)
O2*0.097 (9)0.065 (4)0.070 (7)0.015 (4)0.049 (6)0.019 (4)
N30.149 (8)0.050 (5)0.049 (4)0.007 (4)0.055 (4)0.003 (3)
N3*0.082 (5)0.077 (7)0.079 (6)0.004 (4)0.063 (5)0.003 (4)
C40.10 (1)0.08 (1)0.040 (5)0.043 (6)0.049 (6)0.019 (5)
C4*0.071 (9)0.038 (7)0.09 (1)0.006 (6)0.042 (7)0.013 (6)
C50.074 (4)0.047 (2)0.052 (3)0.006 (3)0.035 (3)0.001 (2)
C5*0.073 (4)0.059 (3)0.049 (3)0.013 (3)0.038 (3)0.013 (2)
C60.079 (4)0.054 (2)0.059 (3)0.004 (2)0.039 (3)0.002 (2)
C6*0.079 (4)0.049 (2)0.049 (3)0.004 (2)0.039 (3)0.002 (2)
C70.070 (5)0.051 (3)0.039 (4)0.001 (4)0.025 (3)0.002 (3)
C7*0.073 (6)0.054 (3)0.034 (4)0.009 (4)0.021 (3)0.007 (3)
C80.099 (9)0.069 (6)0.050 (6)0.037 (4)0.035 (7)0.012 (5)
C8*0.067 (6)0.041 (3)0.059 (7)0.018 (4)0.034 (6)0.024 (3)
C90.10 (2)0.07 (1)0.09 (2)0.009 (10)0.03 (1)0.001 (10)
C9*0.08 (1)0.064 (9)0.08 (1)0.006 (8)0.06 (1)0.006 (8)
C100.040 (7)0.080 (6)0.046 (7)0.008 (6)0.019 (6)0.006 (7)
C10*0.044 (8)0.093 (7)0.040 (7)0.018 (7)0.007 (5)0.012 (7)
C110.092 (8)0.081 (7)0.058 (9)0.013 (5)0.042 (6)0.000 (6)
C11*0.080 (6)0.060 (4)0.045 (7)0.009 (4)0.026 (5)0.002 (5)
C120.12 (1)0.052 (4)0.069 (6)0.001 (4)0.048 (6)0.002 (4)
C12*0.11 (1)0.053 (4)0.087 (8)0.011 (4)0.066 (7)0.018 (4)
Geometric parameters (Å, º) top
Cl1—C101.78 (2)C7—C81.24 (2)
Cl1*—C10*1.67 (2)C7—C121.36 (2)
O2—C41.14 (2)C7*—C8*1.51 (2)
O2*—C4*1.38 (2)C7*—C12*1.41 (2)
N3—C41.26 (2)C8—C91.35 (3)
N3—H3A0.96C8—H80.96
N3—H3B0.96C8*—C9*1.41 (3)
N3*—C4*1.35 (2)C8*—H8*0.96
N3*—H3*A0.96C9—C101.37 (3)
N3*—H3*B0.96C9—H90.96
C4—C51.50 (2)C9*—C10*1.41 (4)
C4*—C5*1.57 (2)C9*—H9*0.96
C5—C61.334 (9)C10—C111.25 (3)
C5—H50.96C10*—C11*1.45 (4)
C5*—C6*1.548 (9)C11—C121.47 (3)
C5*—C6*i1.582 (8)C11—H110.96
C5*—H5*0.96C11*—C12*1.39 (3)
C6—C71.44 (1)C11*—H11*0.96
C6—H60.96C12—H120.96
C6*—C7*1.54 (1)C12*—H12*0.96
C6*—H6*0.96
C4—N3—H3A120C6*—C7*—C8*122.0 (10)
C4—N3—H3B119C6*—C7*—C12*118.6 (9)
H3A—N3—H3B121C8*—C7*—C12*119 (1)
C4*—N3*—H3*A119C7—C8—C9126 (1)
C4*—N3*—H3*B121C7—C8—H8119
H3*A—N3*—H3*B120C9—C8—H8115
O2—C4—N3122 (1)C7*—C8*—C9*117 (1)
O2—C4—C5117 (1)C7*—C8*—H8*119
N3—C4—C5118 (1)C9*—C8*—H8*124
O2*—C4*—N3*124 (1)C8—C9—C10118 (1)
O2*—C4*—C5*131 (1)C8—C9—H9115
N3*—C4*—C5*103.3 (9)C10—C9—H9125
C4—C5—C6123.9 (7)C8*—C9*—C10*120 (1)
C4—C5—H5118C8*—C9*—H9*120
C6—C5—H5118C10*—C9*—H9*119
C4*—C5*—C6*113.3 (6)Cl1—C10—C9120 (2)
C4*—C5*—C6*i117.7 (8)Cl1—C10—C11118 (2)
C4*—C5*—H5*111C9—C10—C11120 (2)
C6*—C5*—C6*i90.2 (4)Cl1*—C10*—C9*119 (2)
C6*—C5*—H5*110Cl1*—C10*—C11*118 (2)
C6*i—C5*—H5*113C9*—C10*—C11*120 (1)
C5—C6—C7127.2 (5)C10—C11—C12117 (1)
C5—C6—H6117C10—C11—H11125
C7—C6—H6116C12—C11—H11117
C5*—C6*—C5*i89.8 (4)C10*—C11*—C12*118 (1)
C5*—C6*—C7*121.6 (5)C10*—C11*—H11*120.3
C5*—C6*—H6*110C12*—C11*—H11*120.6
C5*i—C6*—C7*116.3 (5)C7—C12—C11120 (1)
C5*i—C6*—H6*108C7—C12—H12118
C7*—C6*—H6*109C11—C12—H12121
C6—C7—C8124 (1)C7*—C12*—C11*121 (1)
C6—C7—C12119.6 (9)C7*—C12*—H12*120
C8—C7—C12115 (1)C11*—C12*—H12*119
Symmetry code: (i) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O2ii0.962.102.98 (2)153
N3—H3B···O2iii0.962.303.06 (1)135
N3*—H3*A···O2*ii0.962.042.94 (2)157
N3*—H3*B···O2*iii0.962.053.00 (2)171
Symmetry codes: (ii) x+1, y, z+2; (iii) x+1, y+1/2, z+3/2.
(III) top
Crystal data top
C7H7NOSDx = 1.359 Mg m3
Mr = 153.20Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 25 reflections
Hall symbol: -P 2ac 2abθ = 14.3–14.9°
a = 20.243 (3) ŵ = 0.36 mm1
b = 9.087 (2) ÅT = 298 K
c = 8.137 (2) ÅPlate-like, colorless
V = 1496.9 (4) Å30.7 × 0.3 × 0.05 mm
Z = 8
Data collection top
Rigaku AFC7R
diffractometer
Rint = 0.024
θ–2θ scansθmax = 30°, θmin = 2.5°
Absorption correction: integration
(Coppens et al., 1965)
h = 1428
Tmin = 0.735, Tmax = 0.975k = 012
2476 measured reflectionsl = 011
2188 independent reflections3 standard reflections every 150 reflections
1074 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2H atoms: see text
R[F2 > 2σ(F2)] = 0.049 w = 1/[σ2(Fo2) + (0.0521P)2 + 0.5253P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.142(Δ/σ)max = 0.0001
S = 0.99Δρmax = 0.21 e Å3
2188 reflectionsΔρmin = 0.17 e Å3
116 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*/UeqOcc. (<1)
S10.14123 (4)0.36940 (8)0.2684 (1)0.0751 (3)0.825 (3)
S1*0.1854 (1)0.6366 (2)0.2971 (2)0.0751 (8)0.175 (3)
O20.04607 (9)0.5978 (2)0.8368 (2)0.0613 (5)
N30.0005 (1)0.3727 (2)0.8248 (3)0.0556 (5)
C40.0372 (1)0.4794 (2)0.7633 (3)0.0491 (5)
C50.0685 (1)0.4496 (3)0.6026 (3)0.0504 (5)
C60.1091 (1)0.5451 (3)0.5332 (3)0.0512 (5)
C70.1437 (1)0.5264 (2)0.3782 (3)0.0513 (5)
C80.1889 (2)0.4360 (4)0.1204 (4)0.090 (1)
C90.2089 (2)0.5724 (4)0.1476 (4)0.0841 (9)
C100.1854 (1)0.6366 (2)0.2971 (2)0.0751 (8)0.825 (3)
C10*0.14123 (4)0.36940 (8)0.2684 (1)0.0751 (3)0.175 (3)
H3A0.020 (1)0.382 (3)0.925 (3)0.0745 (1)*
H3B0.013 (1)0.286 (3)0.766 (3)0.0899 (1)*
H50.058 (1)0.355 (3)0.552 (3)0.05255 (8)*
H60.118 (1)0.634 (3)0.585 (3)0.06064 (9)*
H80.200 (2)0.377 (3)0.034 (4)0.1098 (1)*
H90.238 (2)0.624 (4)0.077 (4)0.1233 (2)*
H100.19460.73250.33710.0901*0.825 (3)
H10*0.12030.27700.28520.0901*0.175 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0862 (6)0.0618 (5)0.0773 (6)0.0042 (4)0.0240 (5)0.0149 (4)
S1*0.084 (1)0.073 (1)0.069 (1)0.002 (1)0.0009 (10)0.0079 (10)
O20.088 (1)0.0424 (8)0.0530 (9)0.0058 (8)0.0110 (9)0.0035 (7)
N30.070 (1)0.0427 (10)0.054 (1)0.0030 (10)0.013 (1)0.0010 (10)
C40.059 (1)0.0397 (10)0.049 (1)0.0068 (10)0.001 (1)0.0029 (10)
C50.060 (1)0.042 (1)0.049 (1)0.004 (1)0.000 (1)0.0015 (10)
C60.056 (1)0.048 (1)0.050 (1)0.002 (1)0.002 (1)0.002 (1)
C70.050 (1)0.055 (1)0.049 (1)0.003 (1)0.003 (1)0.003 (1)
C80.103 (2)0.098 (2)0.068 (2)0.025 (2)0.019 (2)0.011 (2)
C90.081 (2)0.102 (2)0.069 (2)0.002 (2)0.016 (2)0.023 (2)
C100.084 (1)0.073 (1)0.069 (1)0.002 (1)0.0009 (10)0.0079 (10)
C10*0.0862 (6)0.0618 (5)0.0773 (6)0.0042 (4)0.0240 (5)0.0149 (4)
Geometric parameters (Å, º) top
S1—C71.684 (2)C6—C71.452 (3)
S1—C81.658 (4)C6—H60.93 (2)
S1*—C71.466 (3)C7—C101.466 (3)
S1*—C91.431 (4)C7—C10*1.684 (2)
O2—C41.244 (3)C8—C91.322 (5)
N3—C41.331 (3)C8—C10*1.658 (4)
N3—H3A0.91 (3)C8—H80.91 (3)
N3—H3B0.96 (3)C9—H90.94 (3)
C4—C51.478 (3)C9—C101.431 (4)
C5—C61.321 (3)C10—H100.95
C5—H50.98 (2)C10*—H10*0.95
C7—S1—C893.4 (2)S1*—C7—C6126.1 (2)
C7—S1*—C9107.2 (2)C10—C7—C6126.1 (2)
C4—N3—H3A121 (1)S1—C8—C9113.5 (3)
C4—N3—H3B124 (1)C10*—C8—C9113.5 (3)
H3A—N3—H3B114 (2)S1—C8—H8118 (2)
O2—C4—N3122.1 (2)C10*—C8—H8118 (2)
O2—C4—C5121.4 (2)C9—C8—H8127 (2)
N3—C4—C5116.5 (2)S1*—C9—C8115.0 (3)
C4—C5—C6121.7 (2)C10—C9—C8115.0 (3)
C4—C5—H5116 (1)S1*—C9—H9121 (2)
C6—C5—H5122 (1)C10—C9—H9121 (2)
C5—C6—C7126.5 (2)C8—C9—H9123 (2)
C5—C6—H6119 (1)C7—C10—C9107.2 (2)
C7—C6—H6113 (1)C7—C10—H10126
S1—C7—C10110.9 (2)C9—C10—H10127
S1*—C7—C10*110.9 (2)C7—C10*—C893.4 (2)
S1—C7—C6123.0 (2)C7—C10*—H10*133
C10*—C7—C6123.0 (2)C8—C10*—H10*133
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O2i0.91 (3)2.01 (3)2.916 (3)169 (2)
N3—H3B···O2ii0.96 (3)2.02 (3)2.970 (3)173 (2)
Symmetry codes: (i) x, y+1, z+2; (ii) x, y1/2, z+3/2.
(IV) top
Crystal data top
C9H9NOZ = 4
Mr = 147.18Dx = 1.253 Mg m3
Monoclinic, P21/aMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yabCell parameters from 25 reflections
a = 16.047 (2) Åθ = 12.2–14.8°
b = 5.084 (2) ŵ = 0.08 mm1
c = 9.584 (2) ÅT = 298 K
β = 94.06 (1)°Prism, colourless
V = 779.9 (3) Å30.8 × 0.3 × 0.2 mm
Data collection top
Rigaku AFC7R
diffractometer
θmax = 27.5°, θmin = 2.5°
θ–2θ scansh = 021
1857 measured reflectionsk = 70
1790 independent reflectionsl = 1212
1259 reflections with I > 2σ(I)3 standard reflections every 150 reflections
Rint = 0.007 intensity decay: 0.8%
Refinement top
Refinement on F2 w = 1/[σ2(Fo2) + (0.0639P)2 + 0.0958P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.040(Δ/σ)max = 0.0001
wR(F2) = 0.121Δρmax = 0.12 e Å3
S = 1.02Δρmin = 0.15 e Å3
1790 reflectionsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
137 parametersExtinction coefficient: 0.066 (8)
All H-atom parameters refined
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
O10.95690 (8)0.7028 (2)1.3471 (1)0.0679 (4)
N20.93750 (9)0.2729 (3)1.3872 (1)0.0549 (4)
C30.93202 (9)0.4845 (3)1.3059 (1)0.0475 (4)
C40.8932 (1)0.4470 (3)1.1619 (1)0.0489 (4)
C50.89926 (9)0.6276 (3)1.0648 (1)0.0477 (3)
C60.86334 (8)0.6225 (3)0.9191 (1)0.0452 (3)
C70.8039 (1)0.4387 (3)0.8718 (2)0.0552 (4)
C80.7713 (1)0.4412 (4)0.7342 (2)0.0669 (5)
C90.7979 (1)0.6235 (4)0.6423 (2)0.0689 (5)
C100.8554 (1)0.8082 (4)0.6870 (2)0.0731 (5)
C110.8882 (1)0.8088 (4)0.8249 (2)0.0619 (4)
H2A0.968 (1)0.287 (4)1.469 (2)0.07089 (6)*
H2B0.929 (1)0.114 (4)1.351 (2)0.06032 (6)*
H40.8634 (10)0.281 (3)1.145 (2)0.05960 (6)*
H50.931 (1)0.784 (4)1.090 (2)0.06950 (6)*
H70.787 (1)0.302 (4)0.934 (2)0.06765 (6)*
H80.732 (1)0.306 (5)0.706 (2)0.09891 (9)*
H90.774 (1)0.621 (4)0.542 (3)0.09725 (8)*
H100.878 (1)0.938 (5)0.629 (2)0.09681 (9)*
H110.929 (1)0.932 (4)0.858 (2)0.07250 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1073 (9)0.0379 (5)0.0536 (6)0.0013 (6)0.0285 (6)0.0027 (5)
N20.0786 (9)0.0416 (7)0.0419 (6)0.0036 (6)0.0137 (6)0.0005 (5)
C30.0600 (8)0.0378 (7)0.0432 (7)0.0027 (6)0.0079 (6)0.0032 (6)
C40.0617 (8)0.0414 (7)0.0419 (7)0.0012 (6)0.0081 (6)0.0023 (6)
C50.0506 (8)0.0458 (7)0.0454 (7)0.0019 (6)0.0057 (6)0.0009 (6)
C60.0477 (7)0.0475 (7)0.0399 (7)0.0056 (6)0.0008 (5)0.0031 (6)
C70.0645 (9)0.0594 (9)0.0408 (7)0.0075 (7)0.0020 (6)0.0026 (7)
C80.078 (1)0.075 (1)0.0460 (8)0.0083 (9)0.0092 (8)0.0040 (8)
C90.081 (1)0.086 (1)0.0383 (8)0.009 (1)0.0037 (7)0.0048 (8)
C100.080 (1)0.087 (1)0.0524 (9)0.002 (1)0.0068 (8)0.0271 (9)
C110.0614 (9)0.066 (1)0.0578 (9)0.0067 (8)0.0016 (7)0.0151 (8)
Geometric parameters (Å, º) top
O1—C31.235 (2)C6—C111.387 (2)
N2—C31.327 (2)C7—C81.384 (2)
N2—H2A0.90 (2)C7—H70.97 (2)
N2—H2B0.89 (2)C8—C91.368 (3)
C3—C41.485 (2)C8—H80.96 (2)
C4—C51.316 (2)C9—C101.363 (3)
C4—H40.98 (2)C9—H91.01 (2)
C5—C61.472 (2)C10—C111.389 (2)
C5—H50.97 (2)C10—H100.95 (2)
C6—C71.388 (2)C11—H110.94 (2)
C3—N2—H2A117 (1)C6—C7—C8120.7 (2)
C3—N2—H2B120 (1)C6—C7—H7119 (1)
H2A—N2—H2B118 (1)C8—C7—H7119 (1)
O1—C3—N2122.3 (1)C7—C8—C9120.3 (2)
O1—C3—C4121.2 (1)C7—C8—H8117 (1)
N2—C3—C4116.6 (1)C9—C8—H8122 (1)
C3—C4—C5121.4 (1)C8—C9—C10120.0 (2)
C3—C4—H4115.6 (10)C8—C9—H9119 (1)
C5—C4—H4123.1 (10)C10—C9—H9120 (1)
C4—C5—C6127.9 (1)C9—C10—C11120.2 (2)
C4—C5—H5117 (1)C9—C10—H10124 (1)
C6—C5—H5114 (1)C11—C10—H10114 (1)
C5—C6—C7122.4 (1)C6—C11—C10120.7 (2)
C5—C6—C11119.6 (1)C6—C11—H11117 (1)
C7—C6—C11118.0 (1)C10—C11—H11121 (1)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.90 (2)2.07 (2)2.960 (2)176 (2)
N2—H2B···O1ii0.89 (2)2.14 (2)3.943 (2)151 (1)
Symmetry codes: (i) x+2, y+1, z+3; (ii) x, y1, z.
(IV') top
Crystal data top
C9H9NOZ = 4
Mr = 147.18Dx = 1.252 Mg m3
Monoclinic, P21/aMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yabCell parameters from 25 reflections
a = 16.191 (2) Åθ = 12.2–14.6°
b = 5.079 (2) ŵ = 0.08 mm1
c = 9.509 (2) ÅT = 298 K
β = 93.37 (2)°Prism, colourless
V = 780.7 (4) Å30.8 × 0.3 × 0.2 mm
Data collection top
Rigaku AFC7R
diffractometer
θmax = 27.5°, θmin = 2.5°
θ–2θ scansh = 021
1859 measured reflectionsk = 70
1793 independent reflectionsl = 1212
1163 reflections with I > 2σ(I)3 standard reflections every 150 reflections
Rint = 0.008 intensity decay: 1.3%
Refinement top
Refinement on F2H atoms: see text
R[F2 > 2σ(F2)] = 0.051 w = 1/[σ2(Fo2) + (0.0927P)2 + 0.0444P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.160(Δ/σ)max = 0.0001
S = 1.05Δρmax = 0.20 e Å3
1793 reflectionsΔρmin = 0.18 e Å3
137 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*/UeqOcc. (<1)
O10.9573 (1)0.7022 (2)1.3477 (2)0.0760 (5)0.955 (2)
O1*0.97630.71041.27570.0757*0.045 (2)
N20.9383 (1)0.2719 (3)1.3887 (2)0.0630 (5)0.955 (2)
N2*0.95770.29721.33330.0629*0.045 (2)
C30.9326 (1)0.4837 (3)1.3065 (2)0.0553 (5)0.955 (2)
C3*0.95880.48301.23210.0551*0.045 (2)
C40.8940 (1)0.4463 (3)1.1627 (2)0.0559 (5)0.955 (2)
C4*0.95790.41991.08020.0558*0.045 (2)
C50.8997 (1)0.6275 (3)1.0647 (2)0.0543 (4)0.955 (2)
C5*0.95350.64260.97340.0542*0.045 (2)
C60.8634 (1)0.6220 (3)0.9189 (2)0.0518 (4)0.955 (2)
C6*0.88600.66800.86280.0519*0.045 (2)
C70.8037 (1)0.4398 (4)0.8733 (2)0.0633 (5)0.955 (2)
C7*0.83590.44480.86520.0632*0.045 (2)
C80.7709 (2)0.4445 (5)0.7351 (2)0.0773 (7)0.955 (2)
C8*0.76770.42040.76930.0772*0.045 (2)
C90.7972 (2)0.6257 (5)0.6420 (2)0.0804 (7)0.955 (2)
C9*0.74960.61920.67110.0803*0.045 (2)
C100.8552 (2)0.8078 (6)0.6856 (2)0.0840 (7)0.955 (2)
C10*0.79970.84250.66870.0840*0.045 (2)
C110.8882 (2)0.8089 (5)0.8230 (2)0.0701 (6)0.955 (2)
C11*0.86790.86690.76460.0700*0.045 (2)
H2A0.967 (1)0.287 (4)1.476 (3)0.06603 (7)*0.955 (2)
H2B0.931 (1)0.117 (5)1.348 (2)0.06755 (7)*0.955 (2)
H2*A0.95830.34791.43060.0755*0.045 (2)
H2*B0.95620.11421.30800.0755*0.045 (2)
H40.862 (1)0.283 (5)1.146 (2)0.07358 (8)*0.955 (2)
H4*0.91930.28441.05530.0670*0.045 (2)
H50.932 (1)0.778 (5)1.091 (2)0.07779 (8)*0.955 (2)
H5*0.95720.80401.02390.0650*0.045 (2)
H70.789 (1)0.319 (4)0.936 (2)0.06496 (7)*0.955 (2)
H7*0.84830.30790.93270.0759*0.045 (2)
H80.738 (2)0.311 (6)0.709 (3)0.1086 (1)*0.955 (2)
H8*0.73320.26670.77100.0927*0.045 (2)
H90.771 (2)0.626 (6)0.541 (3)0.1138 (1)*0.955 (2)
H9*0.70270.60240.60520.0963*0.045 (2)
H100.875 (2)0.925 (6)0.629 (3)0.1029 (1)*0.955 (2)
H10*0.78720.97930.60120.1008*0.045 (2)
H110.933 (2)0.924 (5)0.856 (3)0.08534 (9)*0.955 (2)
H11*0.90231.02050.76290.0841*0.045 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.126 (1)0.0330 (6)0.0644 (8)0.0019 (7)0.0329 (8)0.0027 (5)
N20.099 (1)0.0357 (7)0.0521 (8)0.0034 (7)0.0146 (8)0.0008 (6)
C30.078 (1)0.0344 (8)0.0520 (10)0.0028 (7)0.0106 (8)0.0030 (6)
C40.076 (1)0.0389 (8)0.0511 (9)0.0018 (8)0.0104 (8)0.0027 (7)
C50.064 (1)0.0431 (8)0.0548 (9)0.0026 (8)0.0086 (8)0.0009 (7)
C60.060 (1)0.0459 (8)0.0490 (9)0.0052 (7)0.0016 (7)0.0035 (7)
C70.077 (1)0.060 (1)0.0525 (10)0.0084 (9)0.0051 (9)0.0034 (8)
C80.097 (2)0.076 (1)0.056 (1)0.010 (1)0.017 (1)0.0029 (10)
C90.105 (2)0.088 (2)0.0468 (10)0.010 (1)0.008 (1)0.005 (1)
C100.101 (2)0.091 (2)0.060 (1)0.001 (1)0.006 (1)0.027 (1)
C110.075 (1)0.068 (1)0.066 (1)0.007 (1)0.0018 (10)0.0172 (10)
Geometric parameters (Å, º) top
O1—C31.235 (2)C6*—C7*1.395
O1*—C3*1.254C6*—C11*1.395
N2—C31.330 (2)C7—C81.388 (3)
N2—H2A0.93 (2)C7—H70.89 (2)
N2—H2B0.88 (2)C7*—C8*1.395
N2*—C3*1.349C7*—H7*0.96
N2*—H2*A0.96C8—C91.363 (4)
N2*—H2*B0.96C8—H80.89 (3)
C3—C41.482 (2)C8*—C9*1.395
C3*—C4*1.478C8*—H8*0.96
C4—C51.316 (2)C9—C101.365 (4)
C4—H40.98 (2)C9—H91.03 (3)
C4*—C5*1.519C9*—C10*1.395
C4*—C5*i1.582C9*—H9*0.96
C4*—H4*0.95C10—C111.383 (3)
C5—C61.474 (2)C10—H100.87 (3)
C5—H50.95 (2)C10*—C11*1.395
C5*—C6*1.478C10*—H10*0.96
C5*—H5*0.95C11—H110.97 (3)
C6—C71.390 (3)C11*—H11*0.96
C6—C111.391 (3)
C3—N2—H2A118 (1)C5*—C6*—C7*108.9
C3—N2—H2B117 (1)C5*—C6*—C11*131.1
H2A—N2—H2B120 (1)C7*—C6*—C11*120.0
C3*—N2*—H2*A120C6—C7—C8120.3 (2)
C3*—N2*—H2*B120C6—C7—H7117 (1)
H2*A—N2*—H2*B120C8—C7—H7122 (1)
O1—C3—N2122.1 (2)C6*—C7*—C8*120.0
O1—C3—C4121.2 (1)C6*—C7*—H7*120
N2—C3—C4116.7 (1)C8*—C7*—H7*120
O1*—C3*—N2*114.9C7—C8—C9120.7 (2)
O1*—C3*—C4*120.8C7—C8—H8116 (1)
N2*—C3*—C4*123.0C9—C8—H8122 (1)
C3—C4—C5121.3 (2)C7*—C8*—C9*120.0
C3—C4—H4116 (1)C7*—C8*—H8*120
C5—C4—H4122 (1)C9*—C8*—H8*120
C3*—C4*—C5*119.3C8—C9—C10119.7 (2)
C3*—C4*—C5*i113.6C8—C9—H9118 (1)
C3*—C4*—H4*112C10—C9—H9121 (1)
C5*—C4*—C5*i86.6C8*—C9*—C10*120.0
C5*—C4*—H4*112C8*—C9*—H9*120
C5*i—C4*—H4*112C10*—C9*—H9*120
C4—C5—C6127.7 (2)C9—C10—C11120.7 (2)
C4—C5—H5115 (1)C9—C10—H10123 (1)
C6—C5—H5116 (1)C11—C10—H10116 (1)
C4*—C5*—C4*i93.4C9*—C10*—C11*120.0
C4*—C5*—C6*123.0C9*—C10*—H10*120
C4*—C5*—H5*108C11*—C10*—H10*120
C4*i—C5*—C6*115.8C6—C11—C10120.4 (2)
C4*i—C5*—H5*108C6—C11—H11115 (1)
C6*—C5*—H5*108C10—C11—H11123 (1)
C5—C6—C7122.5 (2)C6*—C11*—C10*120.0
C5—C6—C11119.3 (2)C6*—C11*—H11*120
C7—C6—C11118.2 (2)C10*—C11*—H11*120
Symmetry code: (i) x+2, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1ii0.93 (2)2.02 (2)2.943 (2)172 (2)
N2—H2B···O1iii0.88 (2)2.15 (2)2.939 (2)149 (2)
N2*—H2*A···O1ii0.962.463.257141
N2*—H2*B···O1iii0.962.133.025155
N2—H2A···O1*ii0.93 (2)2.483.404171
N2—H2B···O1*iii0.88 (2)2.313.122153
N2*—H2*A···O1*ii0.962.943.809151
N2*—H2*B···O1*iii0.962.103.049168
Symmetry codes: (ii) x+2, y+1, z+3; (iii) x, y1, z.
(V) top
Crystal data top
C18H16Cl2N2O2Z = 2
Mr = 363.24Dx = 1.432 Mg m3
Triclinic, P1Mo Kα radiation, λ = 0.71073 Å
a = 8.733 (3) ÅCell parameters from 25 reflections
b = 18.578 (9) Åθ = 10.8–14.4°
c = 5.210 (3) ŵ = 0.40 mm1
α = 91.86 (4)°T = 298 K
β = 93.04 (4)°Needle, colourless
γ = 93.21 (3)°0.4 × 0.1 × 0.05 mm
V = 842.2 (7) Å3
Data collection top
Rigaku AFC7R
diffractometer
Rint = 0.029
θ–2θ scansθmax = 25.0°, θmin = 2.5°
Absorption correction: Ψ-scan
(North et al., 1968)
h = 010
Tmin = 0.868, Tmax = 0.980k = 2222
3320 measured reflectionsl = 66
2961 independent reflections3 standard reflections every 150 reflections
1393 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2H-atom parameters not refined
R[F2 > 2σ(F2)] = 0.091 w = 1/[σ2(Fo2) + (0.050P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.221(Δ/σ)max = 0.0001
S = 1.60Δρmax = 0.85 e Å3
2961 reflectionsΔρmin = 0.39 e Å3
217 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
Cl10.2471 (3)0.1787 (1)0.1216 (5)0.0694 (8)
Cl510.9257 (3)0.3186 (1)0.7596 (6)0.091 (1)
O20.8142 (5)0.4996 (3)0.6610 (9)0.043 (1)
O520.1970 (5)0.0077 (3)0.686 (1)0.046 (1)
N30.8547 (6)0.5089 (4)0.238 (1)0.050 (2)
N530.1389 (7)0.0325 (4)0.275 (1)0.062 (2)
C40.7678 (8)0.5029 (4)0.434 (1)0.035 (2)
C50.5967 (7)0.5025 (4)0.368 (1)0.033 (2)
C60.5013 (7)0.4409 (4)0.500 (1)0.037 (2)
C70.4305 (7)0.3791 (4)0.335 (1)0.038 (2)
C80.5020 (8)0.3542 (4)0.126 (2)0.047 (2)
C90.4489 (8)0.2927 (4)0.020 (2)0.049 (2)
C100.3162 (9)0.2564 (4)0.057 (2)0.046 (2)
C110.2410 (8)0.2789 (4)0.264 (2)0.049 (2)
C120.2974 (8)0.3401 (4)0.402 (2)0.047 (2)
C540.2360 (7)0.0217 (4)0.468 (1)0.035 (2)
C550.4053 (7)0.0294 (4)0.409 (1)0.038 (2)
C560.5191 (7)0.0450 (4)0.643 (1)0.040 (2)
C570.6207 (7)0.1132 (4)0.660 (1)0.039 (2)
C580.6154 (8)0.1666 (4)0.479 (2)0.051 (2)
C590.7120 (9)0.2294 (4)0.509 (2)0.055 (2)
C600.8118 (9)0.2389 (4)0.719 (2)0.056 (2)
C610.8216 (9)0.1869 (5)0.899 (2)0.059 (2)
C620.7265 (8)0.1239 (4)0.869 (2)0.052 (2)
H3A0.96720.50990.26710.0581*
H3B0.81420.51200.06400.0581*
H50.57360.49970.17780.0366*
H60.57120.42090.62820.0422*
H80.59770.37930.07740.0496*
H90.50040.27580.16800.0610*
H110.14950.25150.30710.0571*
H120.24500.35420.55760.0526*
H53A0.02920.02920.29910.0655*
H53B0.17340.04570.10930.0655*
H550.42330.06310.27630.0457*
H560.46340.04210.79900.0444*
H580.54510.15960.32910.0584*
H590.70490.26640.38740.0672*
H610.89820.19341.04040.0702*
H620.73280.08801.00320.0562*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.073 (2)0.047 (1)0.087 (2)0.006 (1)0.007 (1)0.010 (1)
Cl510.065 (2)0.059 (1)0.144 (3)0.019 (1)0.006 (2)0.008 (2)
O20.033 (3)0.065 (3)0.031 (3)0.004 (2)0.002 (2)0.005 (3)
O520.031 (3)0.060 (3)0.046 (3)0.000 (2)0.007 (2)0.005 (3)
N30.027 (3)0.090 (5)0.034 (4)0.007 (3)0.007 (3)0.000 (4)
N530.031 (3)0.103 (6)0.052 (5)0.008 (3)0.002 (3)0.030 (4)
C40.039 (4)0.037 (4)0.029 (4)0.004 (3)0.000 (4)0.001 (3)
C50.022 (3)0.047 (4)0.031 (4)0.002 (3)0.000 (3)0.005 (3)
C60.025 (3)0.048 (4)0.038 (4)0.006 (3)0.001 (3)0.010 (4)
C70.028 (4)0.043 (4)0.044 (5)0.005 (3)0.005 (4)0.010 (4)
C80.043 (4)0.053 (5)0.044 (5)0.007 (4)0.007 (4)0.011 (4)
C90.039 (4)0.053 (5)0.058 (6)0.014 (4)0.012 (4)0.007 (4)
C100.044 (4)0.040 (4)0.054 (6)0.004 (3)0.004 (4)0.001 (4)
C110.043 (4)0.059 (5)0.045 (5)0.008 (4)0.008 (4)0.003 (4)
C120.035 (4)0.049 (5)0.055 (5)0.006 (4)0.009 (4)0.007 (4)
C540.031 (4)0.037 (4)0.038 (5)0.005 (3)0.001 (4)0.004 (4)
C550.030 (4)0.039 (4)0.043 (5)0.004 (3)0.001 (3)0.010 (4)
C560.032 (4)0.048 (4)0.039 (5)0.001 (3)0.003 (4)0.006 (4)
C570.022 (3)0.048 (4)0.047 (5)0.002 (3)0.005 (3)0.000 (4)
C580.044 (4)0.054 (5)0.053 (5)0.003 (4)0.001 (4)0.001 (4)
C590.057 (5)0.044 (5)0.063 (6)0.005 (4)0.001 (5)0.004 (4)
C600.043 (5)0.047 (5)0.077 (7)0.000 (4)0.004 (5)0.007 (5)
C610.043 (4)0.061 (5)0.072 (7)0.005 (4)0.011 (4)0.002 (5)
C620.044 (4)0.061 (5)0.049 (5)0.009 (4)0.009 (4)0.002 (4)
Geometric parameters (Å, º) top
Cl1—C101.750 (7)C9—H90.97
Cl51—C601.737 (8)C10—C111.361 (11)
O2—C41.236 (9)C11—C121.378 (11)
O52—C541.230 (9)C11—H110.96
N3—C41.305 (9)C12—H120.99
N3—H3A0.99C54—C551.527 (9)
N3—H3B0.96C55—C561.541 (9)
N53—C541.309 (9)C55—C56ii1.587 (10)
N53—H53A0.97C55—H550.96
N53—H53B0.97C56—C571.502 (10)
C4—C51.515 (9)C56—H560.97
C5—C61.574 (9)C57—C581.393 (11)
C5—C6i1.560 (10)C57—C621.393 (10)
C5—H51.00C58—C591.401 (11)
C6—C71.496 (9)C58—H580.97
C6—H60.98C59—C601.364 (12)
C7—C81.364 (11)C59—H590.95
C7—C121.402 (10)C60—C611.369 (13)
C8—C91.394 (11)C61—C621.397 (11)
C8—H80.98C61—H610.97
C9—C101.390 (11)C62—H620.98
C4—N3—H3A120C7—C12—C11121.5 (7)
C4—N3—H3B123C7—C12—H12120
H3A—N3—H3B117C11—C12—H12118
C54—N53—H53A120O52—C54—N53123.7 (6)
C54—N53—H53B122O52—C54—C55121.1 (6)
H53A—N53—H53B118N53—C54—C55115.2 (6)
O2—C4—N3125.5 (6)C54—C55—C56115.7 (6)
O2—C4—C5119.3 (6)C54—C55—C56ii114.2 (5)
N3—C4—C5115.2 (6)C54—C55—H55112
C4—C5—C6113.5 (5)C56—C55—C56ii89.5 (5)
C4—C5—C6i119.7 (5)C56—C55—H55111
C4—C5—H5112C56ii—C55—H55113
C6—C5—C6i89.0 (5)C55—C56—C55ii90.5 (5)
C6—C5—H5110C55—C56—C57120.0 (6)
C6i—C5—H5111C55—C56—H56109
C5—C6—C5i91.0 (5)C55ii—C56—C57118.6 (5)
C5—C6—C7118.5 (6)C55ii—C56—H56109
C5—C6—H6107C57—C56—H56109
C5i—C6—C7122.5 (5)C56—C57—C58123.9 (6)
C5i—C6—H6110C56—C57—C62118.3 (7)
C7—C6—H6107C58—C57—C62117.8 (6)
C6—C7—C8120.8 (6)C57—C58—C59120.8 (7)
C6—C7—C12121.7 (7)C57—C58—H58119
C8—C7—C12117.3 (6)C59—C58—H58120
C7—C8—C9123.1 (7)C58—C59—C60119.9 (8)
C7—C8—H8119C58—C59—H59120
C9—C8—H8118C60—C59—H59120
C8—C9—C10116.9 (7)Cl51—C60—C59119.2 (7)
C8—C9—H9122Cl51—C60—C61120.0 (7)
C10—C9—H9121C59—C60—C61120.8 (7)
Cl1—C10—C9118.0 (6)C60—C61—C62119.7 (8)
Cl1—C10—C11119.8 (6)C60—C61—H61119
C9—C10—C11122.2 (7)C62—C61—H61121
C10—C11—C12119.0 (7)C57—C62—C61121.0 (7)
C10—C11—H11118C57—C62—H62121
C12—C11—H11123C61—C62—H62118
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O2iii0.991.942.925 (7)173
N3—H3B···O2iv0.962.113.007 (8)156
N53—H53A···O52v0.972.063.005 (7)164
N53—H53B···O52iv0.972.323.163 (9)146
Symmetry codes: (iii) x+2, y+1, z+1; (iv) x, y, z1; (v) x, y, z+1.
 

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