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The title compound, C
18H
14Cl
2N
2O
2S, was synthesized by the reaction of 1,4,5,6-tetrahydropyrimidine-2-thiol and 2-chlorobenzoyl chloride. The dihedral angle between the two chlorobenzene rings is 76.2 (1)°. The ring carbon (and attached H atoms) opposite the C=S group are disordered over two sites. In the crystal structure, there is one intermolecular C—H
O and one intramolecular C—H
N hydrogen bond.
Supporting information
CCDC reference: 621525
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- Disorder in main residue
- R factor = 0.053
- wR factor = 0.186
- Data-to-parameter ratio = 24.7
checkCIF/PLATON results
No syntax errors found
Alert level B
CRYSS02_ALERT_3_B The value of _exptl_crystal_size_min is > 0.6
Minimum crystal size given = 0.640
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.66 mm
PLAT301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
1,3-Bis(2-chlorobenzoyl)-3,4,5,6-tetrahydropyrimidine-2(1
H)-thione
top
Crystal data top
C18H14Cl2N2O2S | F(000) = 808 |
Mr = 393.28 | Dx = 1.467 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ybc | Cell parameters from 5913 reflections |
a = 11.361 (5) Å | θ = 2.4–28.6° |
b = 12.917 (5) Å | µ = 0.50 mm−1 |
c = 12.186 (5) Å | T = 293 K |
β = 95.399 (5)° | Block, translucent dark green |
V = 1780.4 (13) Å3 | 0.66 × 0.64 × 0.64 mm |
Z = 4 | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 3082 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.034 |
Graphite monochromator | θmax = 31.7°, θmin = 1.8° |
φ and ω scans | h = −16→14 |
20918 measured reflections | k = −19→19 |
5828 independent reflections | l = −17→18 |
Refinement top
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.186 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0706P)2 + 0.7185P] where P = (Fo2 + 2Fc2)/3 |
5828 reflections | (Δ/σ)max < 0.001 |
236 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Special details top
Experimental. IR (KBr) (t, cm-1): 2923 (aliphatic C—H), 1705 (C=O), 1677 (C=C),
1585 (C=N), 640 (C—Cl); 1H NMR (CHCl3-d, 90 MHz, p.p.m.): δ 2.42
(p, CH2, 2H, J= 6 Hz), 3.93 (t, 2xCH2, 4H, J=7 Hz), 7.42–7.72 (m, 8H,
aromatic protons). |
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cl1 | 0.09208 (8) | −0.08743 (7) | 0.92252 (7) | 0.0834 (3) | |
Cl2 | 0.33651 (9) | 0.40535 (8) | 1.00332 (8) | 0.0932 (4) | |
S1 | 0.33063 (6) | 0.11111 (5) | 0.81197 (6) | 0.0574 (2) | |
O1 | 0.1565 (3) | −0.11204 (18) | 0.6044 (2) | 0.0879 (9) | |
O2 | 0.1127 (3) | 0.2938 (2) | 0.9430 (2) | 0.0986 (10) | |
N1 | 0.13281 (19) | 0.03135 (15) | 0.70529 (15) | 0.0506 (6) | |
N2 | 0.11184 (18) | 0.18083 (16) | 0.80244 (16) | 0.0512 (6) | |
C1 | 0.2270 (3) | −0.1343 (2) | 0.8845 (3) | 0.0612 (9) | |
C2 | 0.2942 (3) | −0.1907 (3) | 0.9630 (3) | 0.0861 (14) | |
C3 | 0.3992 (4) | −0.2316 (3) | 0.9367 (4) | 0.1037 (18) | |
C4 | 0.4345 (3) | −0.2183 (3) | 0.8332 (5) | 0.1013 (19) | |
C5 | 0.3649 (3) | −0.1622 (2) | 0.7543 (3) | 0.0777 (11) | |
C6 | 0.2604 (2) | −0.11710 (18) | 0.7795 (2) | 0.0588 (8) | |
C7 | 0.1837 (3) | −0.0660 (2) | 0.6889 (2) | 0.0582 (8) | |
C8 | 0.1869 (2) | 0.10767 (16) | 0.77198 (18) | 0.0447 (6) | |
C9 | 0.0204 (3) | 0.0545 (3) | 0.6371 (2) | 0.0714 (10) | |
C10A | −0.0507 (8) | 0.1322 (10) | 0.6711 (12) | 0.077 (3) | 0.52 (2) |
C11 | −0.0167 (3) | 0.1628 (3) | 0.7948 (3) | 0.0826 (11) | |
C12 | 0.1546 (2) | 0.2723 (2) | 0.8590 (2) | 0.0572 (8) | |
C13 | 0.2333 (2) | 0.34165 (18) | 0.8021 (2) | 0.0542 (8) | |
C14 | 0.3123 (2) | 0.4107 (2) | 0.8595 (3) | 0.0642 (9) | |
C15 | 0.3750 (3) | 0.4814 (3) | 0.8057 (4) | 0.0855 (13) | |
C16 | 0.3602 (3) | 0.4857 (3) | 0.6927 (4) | 0.0969 (16) | |
C17 | 0.2845 (3) | 0.4189 (3) | 0.6324 (3) | 0.0831 (12) | |
C18 | 0.2218 (3) | 0.3473 (2) | 0.6871 (2) | 0.0636 (9) | |
C10B | −0.0670 (8) | 0.0966 (9) | 0.7197 (13) | 0.076 (3) | 0.48 (2) |
H3 | 0.44670 | −0.26860 | 0.98930 | 0.1250* | |
H4 | 0.50540 | −0.24700 | 0.81570 | 0.1210* | |
H5 | 0.38890 | −0.15490 | 0.68380 | 0.0930* | |
H9A | 0.03990 | 0.07170 | 0.56350 | 0.0860* | |
H9B | −0.02600 | −0.00860 | 0.63130 | 0.0860* | |
H10A | −0.13240 | 0.10950 | 0.66230 | 0.0920* | 0.52 (2) |
H2 | 0.26890 | −0.20080 | 1.03260 | 0.1030* | |
H11A | −0.05820 | 0.22500 | 0.81370 | 0.0990* | |
H11B | −0.03580 | 0.10740 | 0.84380 | 0.0990* | |
H15 | 0.42730 | 0.52620 | 0.84510 | 0.1030* | |
H16 | 0.40210 | 0.53450 | 0.65590 | 0.1170* | |
H17 | 0.27590 | 0.42230 | 0.55590 | 0.1000* | |
H18 | 0.17090 | 0.30190 | 0.64680 | 0.0760* | |
H10B | −0.04380 | 0.19260 | 0.62490 | 0.0920* | 0.52 (2) |
H10C | −0.13260 | 0.13110 | 0.67790 | 0.0910* | 0.48 (2) |
H10D | −0.09880 | 0.03850 | 0.75760 | 0.0910* | 0.48 (2) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0818 (5) | 0.0931 (6) | 0.0793 (5) | 0.0165 (4) | 0.0285 (4) | 0.0257 (4) |
Cl2 | 0.0868 (6) | 0.0992 (7) | 0.0871 (6) | 0.0137 (5) | −0.0258 (5) | −0.0335 (5) |
S1 | 0.0510 (3) | 0.0419 (3) | 0.0774 (4) | 0.0011 (2) | −0.0032 (3) | −0.0063 (3) |
O1 | 0.122 (2) | 0.0679 (13) | 0.0734 (14) | −0.0098 (13) | 0.0069 (13) | −0.0295 (11) |
O2 | 0.119 (2) | 0.0935 (18) | 0.0892 (16) | −0.0158 (15) | 0.0405 (15) | −0.0420 (14) |
N1 | 0.0622 (12) | 0.0458 (10) | 0.0431 (10) | −0.0085 (8) | 0.0019 (8) | −0.0022 (8) |
N2 | 0.0493 (11) | 0.0471 (10) | 0.0567 (11) | 0.0002 (8) | 0.0028 (9) | −0.0048 (8) |
C1 | 0.0648 (16) | 0.0433 (12) | 0.0764 (17) | −0.0011 (11) | 0.0115 (13) | 0.0065 (12) |
C2 | 0.095 (3) | 0.0669 (19) | 0.097 (2) | 0.0105 (17) | 0.0129 (19) | 0.0263 (18) |
C3 | 0.096 (3) | 0.074 (2) | 0.141 (4) | 0.028 (2) | 0.010 (3) | 0.025 (2) |
C4 | 0.073 (2) | 0.0618 (19) | 0.171 (5) | 0.0158 (16) | 0.022 (3) | −0.012 (2) |
C5 | 0.080 (2) | 0.0518 (15) | 0.105 (2) | −0.0011 (14) | 0.0290 (18) | −0.0132 (16) |
C6 | 0.0628 (15) | 0.0343 (10) | 0.0807 (18) | −0.0067 (10) | 0.0143 (13) | −0.0085 (11) |
C7 | 0.0730 (17) | 0.0449 (12) | 0.0580 (14) | −0.0148 (11) | 0.0132 (12) | −0.0119 (11) |
C8 | 0.0525 (12) | 0.0387 (10) | 0.0426 (10) | −0.0035 (9) | 0.0030 (9) | −0.0007 (8) |
C9 | 0.080 (2) | 0.0722 (18) | 0.0570 (15) | −0.0163 (15) | −0.0191 (14) | 0.0107 (14) |
C10A | 0.058 (4) | 0.074 (6) | 0.093 (7) | 0.003 (4) | −0.024 (4) | −0.003 (5) |
C11 | 0.0524 (16) | 0.094 (2) | 0.103 (2) | −0.0031 (16) | 0.0165 (16) | −0.013 (2) |
C12 | 0.0619 (15) | 0.0469 (12) | 0.0621 (15) | 0.0080 (11) | 0.0025 (12) | −0.0122 (11) |
C13 | 0.0542 (14) | 0.0401 (11) | 0.0660 (15) | 0.0089 (10) | −0.0070 (11) | −0.0035 (10) |
C14 | 0.0553 (15) | 0.0472 (13) | 0.0859 (19) | 0.0088 (11) | −0.0150 (13) | −0.0116 (12) |
C15 | 0.070 (2) | 0.0567 (17) | 0.125 (3) | −0.0079 (14) | −0.0157 (19) | −0.0045 (18) |
C16 | 0.079 (2) | 0.069 (2) | 0.142 (4) | −0.0165 (18) | 0.007 (2) | 0.025 (2) |
C17 | 0.087 (2) | 0.080 (2) | 0.081 (2) | −0.0049 (18) | 0.0011 (18) | 0.0202 (17) |
C18 | 0.0643 (16) | 0.0542 (14) | 0.0700 (17) | −0.0013 (12) | −0.0060 (13) | 0.0060 (12) |
C10B | 0.058 (4) | 0.069 (5) | 0.096 (7) | −0.008 (3) | −0.015 (4) | 0.020 (4) |
Geometric parameters (Å, º) top
Cl1—C1 | 1.751 (4) | C13—C18 | 1.397 (3) |
Cl2—C14 | 1.750 (4) | C13—C14 | 1.404 (4) |
S1—C8 | 1.660 (2) | C14—C15 | 1.364 (5) |
O1—C7 | 1.204 (4) | C15—C16 | 1.373 (7) |
O2—C12 | 1.201 (4) | C16—C17 | 1.380 (5) |
N1—C7 | 1.406 (3) | C17—C18 | 1.377 (5) |
N1—C8 | 1.384 (3) | C2—H2 | 0.9300 |
N1—C9 | 1.487 (4) | C3—H3 | 0.9300 |
N2—C8 | 1.348 (3) | C4—H4 | 0.9300 |
N2—C11 | 1.473 (4) | C5—H5 | 0.9300 |
N2—C12 | 1.430 (3) | C9—H9A | 0.9700 |
C1—C2 | 1.375 (5) | C9—H9B | 0.9700 |
C1—C6 | 1.386 (4) | C10A—H10A | 0.9700 |
C2—C3 | 1.370 (6) | C10A—H10B | 0.9700 |
C3—C4 | 1.370 (8) | C10B—H10D | 0.9700 |
C4—C5 | 1.390 (6) | C10B—H10C | 0.9700 |
C5—C6 | 1.383 (4) | C11—H11B | 0.9700 |
C6—C7 | 1.494 (4) | C11—H11A | 0.9700 |
C9—C10A | 1.376 (12) | C15—H15 | 0.9300 |
C9—C10B | 1.576 (13) | C16—H16 | 0.9300 |
C10A—C11 | 1.571 (15) | C17—H17 | 0.9300 |
C10B—C11 | 1.341 (14) | C18—H18 | 0.9300 |
C12—C13 | 1.483 (3) | | |
| | | |
Cl1···N1 | 3.132 (2) | C13···S1 | 3.175 (3) |
Cl1···C8 | 3.354 (3) | C16···C4v | 3.553 (5) |
Cl2···O2 | 2.955 (4) | C18···C8 | 3.299 (4) |
Cl2···C7i | 3.630 (3) | C18···S1 | 3.577 (3) |
Cl1···H10Bii | 2.9400 | C1···H10Bii | 3.0500 |
Cl1···H11B | 3.0200 | C7···H11Aii | 3.0500 |
Cl1···H11Biii | 2.9900 | C8···H18 | 2.9300 |
Cl2···H3iv | 3.0300 | C9···H9Ax | 2.9600 |
S1···C1 | 3.523 (3) | C13···H10Dviii | 3.0200 |
S1···C5 | 3.628 (3) | C17···H10Dviii | 3.0300 |
S1···C6 | 3.070 (3) | C18···H10Dviii | 2.9500 |
S1···C13 | 3.175 (3) | H2···O1xi | 2.9100 |
S1···C18 | 3.577 (3) | H3···Cl2iv | 3.0300 |
S1···H4v | 3.1300 | H4···S1vi | 3.1300 |
S1···H16vi | 3.1800 | H5···O1 | 2.7800 |
S1···H17i | 3.1200 | H9A···O1 | 2.7400 |
O2···C9i | 3.317 (4) | H9A···C9x | 2.9600 |
O2···Cl2 | 2.955 (4) | H9A···H9Ax | 2.5300 |
O1···H5 | 2.7800 | H9A···H9Bx | 2.5000 |
O1···H11Aii | 2.6200 | H9A···O2ix | 2.4700 |
O1···H2vii | 2.9100 | H9B···O1 | 2.5100 |
O1···H9B | 2.5100 | H9B···O2ii | 2.8500 |
O1···H9A | 2.7400 | H9B···H9Ax | 2.5000 |
O2···H11A | 2.5400 | H10B···Cl1viii | 2.9400 |
O2···H9Bviii | 2.8500 | H10B···C1viii | 3.0500 |
O2···H9Ai | 2.4700 | H10D···C18ii | 2.9500 |
O2···H18i | 2.8000 | H10D···C13ii | 3.0200 |
N1···Cl1 | 3.132 (2) | H10D···C17ii | 3.0300 |
N1···H11B | 2.8400 | H11A···O2 | 2.5400 |
N2···H18 | 2.5900 | H11A···O1viii | 2.6200 |
C1···S1 | 3.523 (3) | H11A···C7viii | 3.0500 |
C1···C8 | 3.426 (4) | H11B···Cl1 | 3.0200 |
C4···C16vi | 3.553 (5) | H11B···N1 | 2.8400 |
C5···S1 | 3.628 (3) | H11B···Cl1iii | 2.9900 |
C6···S1 | 3.070 (3) | H16···S1v | 3.1800 |
C7···Cl2ix | 3.630 (3) | H17···S1ix | 3.1200 |
C8···C1 | 3.426 (4) | H18···N2 | 2.5900 |
C8···Cl1 | 3.354 (3) | H18···C8 | 2.9300 |
C8···C18 | 3.299 (4) | H18···O2ix | 2.8000 |
C9···O2ix | 3.317 (4) | | |
| | | |
C7—N1—C8 | 123.7 (2) | C1—C2—H2 | 121.00 |
C7—N1—C9 | 116.3 (2) | C3—C2—H2 | 121.00 |
C8—N1—C9 | 119.7 (2) | C2—C3—H3 | 120.00 |
C8—N2—C11 | 121.4 (2) | C4—C3—H3 | 120.00 |
C8—N2—C12 | 121.1 (2) | C3—C4—H4 | 120.00 |
C11—N2—C12 | 116.8 (2) | C5—C4—H4 | 120.00 |
Cl1—C1—C2 | 116.2 (3) | C4—C5—H5 | 120.00 |
Cl1—C1—C6 | 120.8 (2) | C6—C5—H5 | 120.00 |
C2—C1—C6 | 123.0 (3) | N1—C9—H9A | 108.00 |
C1—C2—C3 | 118.7 (4) | N1—C9—H9B | 108.00 |
C2—C3—C4 | 120.3 (4) | C10A—C9—H9A | 108.00 |
C3—C4—C5 | 120.4 (4) | C10A—C9—H9B | 108.00 |
C4—C5—C6 | 120.7 (3) | H9A—C9—H9B | 107.00 |
C1—C6—C5 | 116.9 (3) | C10B—C9—H9A | 136.00 |
C1—C6—C7 | 124.2 (2) | C10B—C9—H9B | 88.00 |
C5—C6—C7 | 118.4 (2) | C9—C10A—H10A | 109.00 |
O1—C7—N1 | 119.2 (3) | C9—C10A—H10B | 109.00 |
O1—C7—C6 | 119.9 (3) | C11—C10A—H10A | 109.00 |
N1—C7—C6 | 120.6 (2) | C11—C10A—H10B | 109.00 |
S1—C8—N1 | 124.16 (17) | H10A—C10A—H10B | 108.00 |
S1—C8—N2 | 122.05 (17) | C9—C10B—H10C | 109.00 |
N1—C8—N2 | 113.8 (2) | C9—C10B—H10D | 109.00 |
N1—C9—C10A | 118.4 (6) | C11—C10B—H10C | 109.00 |
N1—C9—C10B | 105.8 (5) | C11—C10B—H10D | 109.00 |
C9—C10A—C11 | 112.0 (8) | H10C—C10B—H10D | 108.00 |
C9—C10B—C11 | 113.7 (7) | C10B—C11—H11A | 120.00 |
N2—C11—C10B | 120.0 (5) | C10B—C11—H11B | 81.00 |
N2—C11—C10A | 104.7 (4) | C10A—C11—H11A | 111.00 |
O2—C12—C13 | 124.3 (3) | N2—C11—H11A | 111.00 |
N2—C12—C13 | 117.8 (2) | N2—C11—H11B | 111.00 |
O2—C12—N2 | 117.3 (2) | C10A—C11—H11B | 111.00 |
C12—C13—C18 | 119.8 (2) | H11A—C11—H11B | 109.00 |
C14—C13—C18 | 117.5 (2) | C14—C15—H15 | 120.00 |
C12—C13—C14 | 122.4 (2) | C16—C15—H15 | 120.00 |
Cl2—C14—C15 | 117.9 (3) | C15—C16—H16 | 119.00 |
C13—C14—C15 | 121.6 (3) | C17—C16—H16 | 119.00 |
Cl2—C14—C13 | 120.4 (2) | C18—C17—H17 | 120.00 |
C14—C15—C16 | 119.3 (4) | C16—C17—H17 | 120.00 |
C15—C16—C17 | 121.3 (4) | C17—C18—H18 | 119.00 |
C16—C17—C18 | 119.1 (3) | C13—C18—H18 | 119.00 |
C13—C18—C17 | 121.1 (3) | | |
| | | |
C8—N1—C7—O1 | −153.1 (3) | C1—C2—C3—C4 | −1.6 (6) |
C9—N1—C7—O1 | 20.6 (4) | C2—C3—C4—C5 | 0.8 (6) |
C8—N1—C7—C6 | 33.5 (4) | C3—C4—C5—C6 | 1.4 (5) |
C9—N1—C7—C6 | −152.8 (2) | C4—C5—C6—C1 | −2.6 (4) |
C7—N1—C8—S1 | 18.8 (3) | C4—C5—C6—C7 | −174.5 (3) |
C9—N1—C8—S1 | −154.69 (19) | C1—C6—C7—O1 | −120.1 (3) |
C7—N1—C8—N2 | −161.3 (2) | C5—C6—C7—N1 | −135.4 (3) |
C9—N1—C8—N2 | 25.2 (3) | C1—C6—C7—N1 | 53.3 (4) |
C7—N1—C9—C10A | 160.8 (6) | C5—C6—C7—O1 | 51.2 (4) |
C8—N1—C9—C10A | −25.2 (7) | N1—C9—C10A—C11 | −15.9 (10) |
C11—N2—C8—S1 | −162.0 (2) | C9—C10A—C11—N2 | 50.8 (8) |
C12—N2—C8—N1 | −171.7 (2) | O2—C12—C13—C14 | 32.7 (4) |
C12—N2—C8—S1 | 8.2 (3) | O2—C12—C13—C18 | −140.8 (3) |
C11—N2—C8—N1 | 18.1 (3) | N2—C12—C13—C14 | −157.0 (2) |
C8—N2—C12—O2 | −128.3 (3) | N2—C12—C13—C18 | 29.6 (3) |
C8—N2—C11—C10A | −55.5 (6) | C12—C13—C14—Cl2 | 9.0 (3) |
C12—N2—C11—C10A | 133.8 (5) | C12—C13—C14—C15 | −173.1 (3) |
C11—N2—C12—C13 | −128.7 (3) | C18—C13—C14—Cl2 | −177.4 (2) |
C11—N2—C12—O2 | 42.4 (4) | C18—C13—C14—C15 | 0.5 (4) |
C8—N2—C12—C13 | 60.7 (3) | C12—C13—C18—C17 | 172.9 (3) |
C2—C1—C6—C7 | 173.2 (3) | C14—C13—C18—C17 | −0.9 (4) |
C2—C1—C6—C5 | 1.8 (4) | Cl2—C14—C15—C16 | 178.4 (3) |
C6—C1—C2—C3 | 0.2 (5) | C13—C14—C15—C16 | 0.4 (5) |
Cl1—C1—C6—C5 | −176.2 (2) | C14—C15—C16—C17 | −1.0 (5) |
Cl1—C1—C2—C3 | 178.3 (3) | C15—C16—C17—C18 | 0.7 (5) |
Cl1—C1—C6—C7 | −4.8 (4) | C16—C17—C18—C13 | 0.3 (5) |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x, y−1/2, −z+3/2; (iii) −x, −y, −z+2; (iv) −x+1, −y, −z+2; (v) −x+1, y+1/2, −z+3/2; (vi) −x+1, y−1/2, −z+3/2; (vii) x, −y−1/2, z−1/2; (viii) −x, y+1/2, −z+3/2; (ix) x, −y+1/2, z−1/2; (x) −x, −y, −z+1; (xi) x, −y−1/2, z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···O2ix | 0.97 | 2.47 | 3.317 (4) | 146 |
C18—H18···N2 | 0.93 | 2.59 | 2.914 (4) | 101 |
Symmetry code: (ix) x, −y+1/2, z−1/2. |
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