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In the crystal structure of the title compound, 2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidin-1-ium 3-chlorobenzoate, C
12H
14ClN
4+·C
7H
4ClO
2−, the cation interacts with the carboxylate group of the anion through a pair of N—H
O hydrogen bonds, forming a cyclic hydrogen-bonded motif [graph-set notation
R22(8)]. This motif self-assembles through a complementary
DDAA array of quadruple hydrogen bonds. The pyrimethamine cations are paired about inversion centers through N—H
N hydrogen bonds involving a pyrimidine N atom and the 4-amino group of the pyrimethamine cations. Concurrent with hydrogen bonding are Cl
Cl and sandwich stacking interactions.
Supporting information
CCDC reference: 256151
Key indicators
- Single-crystal X-ray study
- T = 170 K
- Mean (C-C) = 0.004 Å
- R factor = 0.044
- wR factor = 0.122
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - C15 .. 5.11 su
PLAT420_ALERT_2_C D-H Without Acceptor N4 - H4B ... ?
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C12 H14 Cl N4
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: PLATON (Spek, 2003}.
2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidin-1-ium 3-chlorobenzoate
top
Crystal data top
C12H14ClN4+·C7H4ClO2− | Z = 2 |
Mr = 405.27 | F(000) = 420 |
Triclinic, P1 | Dx = 1.444 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.139 (2) Å | Cell parameters from 2044 reflections |
b = 10.337 (2) Å | θ = 3.1–26.1° |
c = 11.121 (2) Å | µ = 0.37 mm−1 |
α = 65.90 (3)° | T = 170 K |
β = 82.80 (3)° | Prism, colourless |
γ = 76.45 (3)° | 0.4 × 0.3 × 0.1 mm |
V = 931.8 (4) Å3 | |
Data collection top
Kuma KM-4-CCD κ-geometry diffractometer | 3616 independent reflections |
Radiation source: fine-focus sealed tube | 2359 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
ω scans | θmax = 26.1°, θmin = 3.1° |
Absorption correction: numerical (CrysAlis RED; Clark & Reid, 1995; Oxford Diffraction, 2004) | h = −11→9 |
Tmin = 0.770, Tmax = 0.924 | k = −12→12 |
7913 measured reflections | l = −12→13 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0619P)2] where P = (Fo2 + 2Fc2)/3 |
3616 reflections | (Δ/σ)max < 0.001 |
245 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All e.s.d.'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 | |
Cl1 | 0.77459 (8) | −0.74814 (7) | 0.65211 (8) | 0.0471 (3) | |
N1 | 0.6618 (2) | 0.1332 (2) | 0.26512 (19) | 0.0269 (7) | |
N2 | 0.5194 (2) | 0.3155 (2) | 0.0992 (2) | 0.0311 (7) | |
N3 | 0.5327 (2) | 0.0799 (2) | 0.12575 (19) | 0.0248 (7) | |
N4 | 0.5461 (2) | −0.1560 (2) | 0.1608 (2) | 0.0302 (7) | |
C2 | 0.5702 (3) | 0.1749 (3) | 0.1636 (2) | 0.0247 (8) | |
C4 | 0.5780 (3) | −0.0617 (2) | 0.2018 (2) | 0.0236 (8) | |
C5 | 0.6600 (2) | −0.1108 (2) | 0.3193 (2) | 0.0233 (8) | |
C6 | 0.7077 (3) | −0.0093 (3) | 0.3440 (2) | 0.0251 (8) | |
C7 | 0.8112 (3) | −0.0420 (3) | 0.4525 (3) | 0.0327 (9) | |
C8 | 0.7296 (3) | −0.0655 (3) | 0.5859 (3) | 0.0460 (11) | |
C9 | 0.6923 (3) | −0.2685 (2) | 0.4057 (2) | 0.0245 (8) | |
C10 | 0.5939 (3) | −0.3272 (3) | 0.5105 (2) | 0.0295 (8) | |
C11 | 0.6181 (3) | −0.4734 (3) | 0.5874 (3) | 0.0313 (8) | |
C12 | 0.7421 (3) | −0.5629 (3) | 0.5590 (3) | 0.0294 (8) | |
C13 | 0.8415 (3) | −0.5086 (3) | 0.4559 (3) | 0.0299 (8) | |
C14 | 0.8170 (3) | −0.3615 (3) | 0.3805 (2) | 0.0282 (8) | |
Cl2 | 0.93722 (9) | 0.94582 (8) | −0.11886 (7) | 0.0502 (3) | |
O1 | 0.80158 (19) | 0.33299 (18) | 0.25822 (18) | 0.0381 (6) | |
O2 | 0.63366 (18) | 0.52881 (17) | 0.14315 (16) | 0.0323 (6) | |
C15 | 0.7665 (3) | 0.4624 (3) | 0.1799 (2) | 0.0296 (9) | |
C16 | 0.8918 (3) | 0.5475 (3) | 0.1271 (2) | 0.0258 (8) | |
C17 | 0.8624 (3) | 0.6897 (3) | 0.0353 (2) | 0.0275 (8) | |
C18 | 0.9749 (3) | 0.7684 (3) | −0.0036 (2) | 0.0309 (9) | |
C19 | 1.1169 (3) | 0.7081 (3) | 0.0459 (3) | 0.0372 (10) | |
C20 | 1.1480 (3) | 0.5662 (3) | 0.1333 (3) | 0.0367 (10) | |
C21 | 1.0369 (3) | 0.4844 (3) | 0.1737 (2) | 0.0310 (8) | |
H1 | 0.69170 | 0.19790 | 0.28030 | 0.0320* | |
H2A | 0.46250 | 0.34540 | 0.03320 | 0.0370* | |
H2B | 0.54330 | 0.37670 | 0.12340 | 0.0370* | |
H4A | 0.49890 | −0.12560 | 0.08910 | 0.0360* | |
H4B | 0.57280 | −0.24740 | 0.20610 | 0.0360* | |
H7A | 0.86280 | 0.03750 | 0.42860 | 0.0390* | |
H7B | 0.88680 | −0.12820 | 0.46050 | 0.0390* | |
H8A | 0.65190 | 0.01780 | 0.57810 | 0.0690* | |
H8B | 0.80010 | −0.07980 | 0.64950 | 0.0690* | |
H8C | 0.68550 | −0.14930 | 0.61390 | 0.0690* | |
H10 | 0.51000 | −0.26630 | 0.52870 | 0.0350* | |
H11 | 0.55200 | −0.51090 | 0.65720 | 0.0380* | |
H13 | 0.92430 | −0.57050 | 0.43730 | 0.0360* | |
H14 | 0.88480 | −0.32440 | 0.31210 | 0.0340* | |
H17 | 0.76730 | 0.73150 | 0.00030 | 0.0330* | |
H19 | 1.19120 | 0.76300 | 0.02050 | 0.0450* | |
H20 | 1.24430 | 0.52450 | 0.16560 | 0.0440* | |
H21 | 1.05910 | 0.38790 | 0.23170 | 0.0370* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0595 (5) | 0.0213 (4) | 0.0498 (5) | −0.0079 (3) | −0.0113 (4) | −0.0009 (3) |
N1 | 0.0345 (11) | 0.0220 (11) | 0.0271 (12) | −0.0088 (9) | −0.0086 (10) | −0.0088 (10) |
N2 | 0.0371 (12) | 0.0219 (11) | 0.0348 (13) | −0.0059 (9) | −0.0144 (10) | −0.0080 (10) |
N3 | 0.0275 (11) | 0.0219 (11) | 0.0250 (12) | −0.0074 (9) | −0.0041 (9) | −0.0071 (9) |
N4 | 0.0423 (12) | 0.0223 (11) | 0.0273 (12) | −0.0076 (9) | −0.0127 (10) | −0.0072 (10) |
C2 | 0.0252 (13) | 0.0249 (13) | 0.0223 (14) | −0.0072 (10) | −0.0004 (11) | −0.0066 (11) |
C4 | 0.0252 (13) | 0.0228 (13) | 0.0240 (14) | −0.0076 (10) | −0.0008 (11) | −0.0090 (11) |
C5 | 0.0267 (13) | 0.0216 (13) | 0.0206 (14) | −0.0043 (10) | −0.0023 (11) | −0.0072 (11) |
C6 | 0.0282 (13) | 0.0253 (13) | 0.0216 (14) | −0.0065 (10) | −0.0015 (11) | −0.0081 (11) |
C7 | 0.0387 (15) | 0.0246 (14) | 0.0359 (16) | −0.0060 (11) | −0.0122 (12) | −0.0101 (12) |
C8 | 0.0587 (19) | 0.0499 (19) | 0.0323 (18) | −0.0084 (15) | −0.0113 (14) | −0.0176 (15) |
C9 | 0.0319 (13) | 0.0217 (13) | 0.0207 (14) | −0.0062 (10) | −0.0096 (11) | −0.0062 (11) |
C10 | 0.0325 (14) | 0.0267 (14) | 0.0279 (15) | −0.0040 (11) | −0.0026 (12) | −0.0098 (12) |
C11 | 0.0354 (15) | 0.0297 (14) | 0.0264 (15) | −0.0116 (12) | −0.0005 (12) | −0.0060 (12) |
C12 | 0.0408 (15) | 0.0183 (13) | 0.0279 (15) | −0.0058 (11) | −0.0140 (12) | −0.0044 (11) |
C13 | 0.0339 (14) | 0.0263 (14) | 0.0302 (15) | −0.0008 (11) | −0.0070 (12) | −0.0130 (12) |
C14 | 0.0342 (14) | 0.0271 (14) | 0.0236 (14) | −0.0082 (11) | −0.0039 (11) | −0.0083 (12) |
Cl2 | 0.0711 (5) | 0.0346 (4) | 0.0417 (5) | −0.0234 (4) | −0.0111 (4) | −0.0024 (3) |
O1 | 0.0519 (11) | 0.0224 (10) | 0.0400 (12) | −0.0112 (8) | −0.0178 (9) | −0.0057 (9) |
O2 | 0.0340 (10) | 0.0286 (10) | 0.0333 (11) | −0.0072 (8) | −0.0081 (8) | −0.0088 (9) |
C15 | 0.0438 (16) | 0.0259 (14) | 0.0244 (15) | −0.0094 (12) | −0.0062 (12) | −0.0125 (12) |
C16 | 0.0345 (14) | 0.0247 (13) | 0.0229 (14) | −0.0051 (11) | −0.0039 (11) | −0.0136 (12) |
C17 | 0.0326 (14) | 0.0271 (14) | 0.0258 (15) | −0.0057 (11) | −0.0038 (11) | −0.0129 (12) |
C18 | 0.0411 (16) | 0.0294 (14) | 0.0250 (15) | −0.0116 (12) | −0.0009 (12) | −0.0110 (12) |
C19 | 0.0367 (16) | 0.0465 (18) | 0.0334 (17) | −0.0170 (13) | 0.0036 (13) | −0.0174 (14) |
C20 | 0.0310 (15) | 0.0487 (18) | 0.0349 (17) | −0.0044 (13) | −0.0038 (13) | −0.0220 (15) |
C21 | 0.0387 (15) | 0.0264 (14) | 0.0276 (15) | −0.0001 (11) | −0.0052 (12) | −0.0127 (12) |
Geometric parameters (Å, º) top
Cl1—C12 | 1.737 (3) | C11—C12 | 1.378 (4) |
Cl2—C18 | 1.738 (3) | C12—C13 | 1.381 (4) |
O1—C15 | 1.252 (3) | C13—C14 | 1.383 (4) |
O2—C15 | 1.272 (3) | C7—H7A | 0.9696 |
N1—C6 | 1.365 (4) | C7—H7B | 0.9703 |
N1—C2 | 1.353 (3) | C8—H8C | 0.9600 |
N2—C2 | 1.326 (4) | C8—H8A | 0.9598 |
N3—C2 | 1.338 (4) | C8—H8B | 0.9599 |
N3—C4 | 1.350 (3) | C10—H10 | 0.9296 |
N4—C4 | 1.331 (3) | C11—H11 | 0.9296 |
N1—H1 | 0.8602 | C13—H13 | 0.9310 |
N2—H2A | 0.8601 | C14—H14 | 0.9298 |
N2—H2B | 0.8596 | C15—C16 | 1.520 (4) |
N4—H4A | 0.8595 | C16—C17 | 1.390 (4) |
N4—H4B | 0.8603 | C16—C21 | 1.394 (4) |
C4—C5 | 1.433 (3) | C17—C18 | 1.378 (4) |
C5—C9 | 1.495 (3) | C18—C19 | 1.377 (4) |
C5—C6 | 1.359 (4) | C19—C20 | 1.374 (5) |
C6—C7 | 1.506 (4) | C20—C21 | 1.388 (4) |
C7—C8 | 1.526 (4) | C17—H17 | 0.9301 |
C9—C14 | 1.389 (4) | C19—H19 | 0.9298 |
C9—C10 | 1.397 (3) | C20—H20 | 0.9297 |
C10—C11 | 1.378 (4) | C21—H21 | 0.9299 |
| | | |
Cl1···Cl2i | 3.2969 (13) | C21···C17xi | 3.405 (4) |
Cl1···N4ii | 3.471 (2) | C21···C13vi | 3.430 (4) |
Cl2···Cl2iii | 3.6526 (14) | C21···C16xi | 3.461 (3) |
Cl2···Cl1iv | 3.2969 (13) | C2···H19xi | 2.7968 |
Cl2···H8Bv | 3.1303 | C4···H4Aix | 3.0863 |
O1···C13vi | 3.327 (4) | C5···H8Aviii | 3.0245 |
O1···N1 | 2.643 (3) | C9···H4B | 2.5036 |
O2···N2vii | 2.856 (3) | C9···H8C | 3.0234 |
O2···N2 | 2.877 (3) | C9···H7B | 2.7992 |
O2···N4vi | 3.249 (3) | C10···H8C | 2.8451 |
O1···H2B | 2.8032 | C11···H20xiii | 2.9623 |
O1···H21 | 2.5027 | C13···H13xii | 2.9851 |
O1···H1 | 1.8259 | C14···H13xii | 3.0738 |
O1···H7A | 2.8234 | C14···H4B | 2.8490 |
O2···H2B | 2.0343 | C15···H2B | 2.6388 |
O2···H4Bvi | 2.6025 | C15···H2Avii | 3.0648 |
O2···H17 | 2.5298 | C15···H1 | 2.7168 |
O2···H11viii | 2.5904 | C16···H14vi | 2.8535 |
O2···H2Avii | 2.0306 | C17···H14vi | 3.0523 |
N1···O1 | 2.643 (3) | C21···H14vi | 2.9779 |
N2···O2 | 2.877 (3) | C21···H13vi | 2.8519 |
N2···O2vii | 2.856 (3) | H1···O1 | 1.8259 |
N2···C15 | 3.382 (4) | H1···H2B | 2.2550 |
N3···N4ix | 3.091 (3) | H1···H7A | 2.2611 |
N4···C17x | 3.390 (4) | H1···C15 | 2.7168 |
N4···C14 | 3.380 (3) | H2A···O2vii | 2.0306 |
N4···Cl1ii | 3.471 (2) | H2A···H17vii | 2.5301 |
N4···O2x | 3.249 (3) | H2A···C15vii | 3.0648 |
N4···N3ix | 3.091 (3) | H2B···O1 | 2.8032 |
N2···H19xi | 2.9016 | H2B···H1 | 2.2550 |
N3···H4Aix | 2.2810 | H2B···C15 | 2.6388 |
N4···H17x | 2.8834 | H2B···O2 | 2.0343 |
C2···C19xi | 3.566 (4) | H4A···N3ix | 2.2810 |
C8···C9 | 3.532 (4) | H4A···H4Aix | 2.5461 |
C9···C8 | 3.532 (4) | H4A···C4ix | 3.0863 |
C11···C11ii | 3.350 (4) | H4B···C9 | 2.5036 |
C13···C14xii | 3.510 (4) | H4B···C14 | 2.8490 |
C13···C15x | 3.370 (4) | H4B···O2x | 2.6025 |
C13···C21x | 3.430 (4) | H7A···O1 | 2.8234 |
C13···C13xii | 3.238 (4) | H7A···H1 | 2.2611 |
C13···C16x | 3.448 (4) | H7B···C9 | 2.7992 |
C13···O1x | 3.327 (4) | H8A···H10viii | 2.5232 |
C14···N4 | 3.380 (3) | H8A···C5viii | 3.0245 |
C14···C13xii | 3.510 (4) | H8B···Cl2xiv | 3.1303 |
C14···C15x | 3.532 (4) | H8C···C9 | 3.0234 |
C14···C21x | 3.493 (4) | H8C···C10 | 2.8451 |
C14···C16x | 3.267 (4) | H10···H8Aviii | 2.5232 |
C15···C14vi | 3.532 (4) | H11···O2viii | 2.5904 |
C15···C13vi | 3.370 (4) | H13···C14xii | 3.0738 |
C15···C19xi | 3.551 (4) | H13···C21x | 2.8519 |
C15···N2 | 3.382 (4) | H13···C13xii | 2.9851 |
C15···C20xi | 3.589 (4) | H14···C17x | 3.0523 |
C16···C16xi | 3.581 (4) | H14···C21x | 2.9779 |
C16···C21xi | 3.461 (3) | H14···C16x | 2.8535 |
C16···C13vi | 3.448 (4) | H17···O2 | 2.5298 |
C16···C14vi | 3.267 (4) | H17···N4vi | 2.8834 |
C17···N4vi | 3.390 (4) | H17···H2Avii | 2.5301 |
C17···C21xi | 3.405 (4) | H19···N2xi | 2.9016 |
C19···C15xi | 3.551 (4) | H19···C2xi | 2.7968 |
C19···C2xi | 3.566 (4) | H20···C11xiii | 2.9623 |
C20···C15xi | 3.589 (4) | H21···O1 | 2.5027 |
C21···C14vi | 3.493 (4) | | |
| | | |
C2—N1—C6 | 121.4 (2) | H7A—C7—H7B | 107.74 |
C2—N3—C4 | 116.9 (2) | C7—C8—H8A | 109.46 |
C2—N1—H1 | 119.30 | C7—C8—H8B | 109.45 |
C6—N1—H1 | 119.28 | C7—C8—H8C | 109.44 |
C2—N2—H2A | 119.93 | H8A—C8—H8B | 109.50 |
C2—N2—H2B | 120.03 | H8A—C8—H8C | 109.47 |
H2A—N2—H2B | 120.04 | H8B—C8—H8C | 109.51 |
H4A—N4—H4B | 120.01 | C9—C10—H10 | 119.25 |
C4—N4—H4A | 120.03 | C11—C10—H10 | 119.22 |
C4—N4—H4B | 119.96 | C10—C11—H11 | 120.60 |
N1—C2—N3 | 122.3 (3) | C12—C11—H11 | 120.62 |
N2—C2—N3 | 119.9 (2) | C12—C13—H13 | 120.30 |
N1—C2—N2 | 117.8 (3) | C14—C13—H13 | 120.27 |
N3—C4—N4 | 116.7 (2) | C9—C14—H14 | 119.60 |
N3—C4—C5 | 122.6 (2) | C13—C14—H14 | 119.62 |
N4—C4—C5 | 120.6 (2) | O1—C15—O2 | 125.0 (3) |
C4—C5—C6 | 117.1 (2) | O1—C15—C16 | 117.5 (2) |
C4—C5—C9 | 119.44 (19) | O2—C15—C16 | 117.5 (2) |
C6—C5—C9 | 123.5 (2) | C15—C16—C17 | 120.7 (3) |
N1—C6—C5 | 118.9 (2) | C15—C16—C21 | 119.9 (2) |
N1—C6—C7 | 116.4 (3) | C17—C16—C21 | 119.4 (3) |
C5—C6—C7 | 124.7 (3) | C16—C17—C18 | 119.7 (3) |
C6—C7—C8 | 113.3 (2) | Cl2—C18—C17 | 119.3 (2) |
C5—C9—C10 | 120.7 (2) | Cl2—C18—C19 | 119.6 (2) |
C5—C9—C14 | 121.0 (2) | C17—C18—C19 | 121.1 (3) |
C10—C9—C14 | 118.2 (2) | C18—C19—C20 | 119.5 (3) |
C9—C10—C11 | 121.5 (3) | C19—C20—C21 | 120.5 (3) |
C10—C11—C12 | 118.8 (3) | C16—C21—C20 | 119.7 (3) |
Cl1—C12—C11 | 120.1 (2) | C16—C17—H17 | 120.18 |
Cl1—C12—C13 | 118.7 (2) | C18—C17—H17 | 120.16 |
C11—C12—C13 | 121.2 (3) | C18—C19—H19 | 120.29 |
C12—C13—C14 | 119.4 (3) | C20—C19—H19 | 120.20 |
C9—C14—C13 | 120.8 (2) | C19—C20—H20 | 119.78 |
C6—C7—H7A | 108.93 | C21—C20—H20 | 119.68 |
C6—C7—H7B | 108.91 | C16—C21—H21 | 120.12 |
C8—C7—H7A | 108.90 | C20—C21—H21 | 120.14 |
C8—C7—H7B | 108.87 | | |
| | | |
C6—N1—C2—N2 | 173.9 (2) | C14—C9—C10—C11 | −0.3 (4) |
C6—N1—C2—N3 | −7.4 (4) | C5—C9—C14—C13 | −176.1 (2) |
C2—N1—C6—C5 | 0.1 (4) | C10—C9—C14—C13 | 1.1 (4) |
C2—N1—C6—C7 | 179.2 (2) | C9—C10—C11—C12 | −0.3 (4) |
C4—N3—C2—N1 | 6.5 (4) | C10—C11—C12—C13 | 0.2 (5) |
C4—N3—C2—N2 | −174.8 (2) | C10—C11—C12—Cl1 | −179.0 (2) |
C2—N3—C4—N4 | −177.2 (2) | C11—C12—C13—C14 | 0.6 (5) |
C2—N3—C4—C5 | 1.1 (3) | Cl1—C12—C13—C14 | 179.8 (2) |
N4—C4—C5—C9 | −8.0 (3) | C12—C13—C14—C9 | −1.3 (4) |
N3—C4—C5—C6 | −7.9 (3) | O1—C15—C16—C17 | 177.1 (2) |
N3—C4—C5—C9 | 173.7 (2) | O1—C15—C16—C21 | −4.8 (4) |
N4—C4—C5—C6 | 170.4 (2) | O2—C15—C16—C17 | −4.2 (4) |
C9—C5—C6—N1 | −174.6 (2) | O2—C15—C16—C21 | 173.9 (2) |
C9—C5—C6—C7 | 6.3 (4) | C15—C16—C17—C18 | 175.0 (2) |
C4—C5—C9—C10 | −92.0 (3) | C21—C16—C17—C18 | −3.1 (4) |
C4—C5—C6—C7 | −172.0 (2) | C15—C16—C21—C20 | −174.8 (3) |
C4—C5—C6—N1 | 7.0 (3) | C17—C16—C21—C20 | 3.3 (4) |
C4—C5—C9—C14 | 85.1 (3) | C16—C17—C18—Cl2 | 179.8 (2) |
C6—C5—C9—C10 | 89.7 (3) | C16—C17—C18—C19 | 0.7 (4) |
C6—C5—C9—C14 | −93.2 (3) | Cl2—C18—C19—C20 | −177.6 (2) |
C5—C6—C7—C8 | −83.2 (4) | C17—C18—C19—C20 | 1.4 (4) |
N1—C6—C7—C8 | 97.7 (3) | C18—C19—C20—C21 | −1.2 (5) |
C5—C9—C10—C11 | 176.9 (2) | C19—C20—C21—C16 | −1.2 (4) |
Symmetry codes: (i) x, y−2, z+1; (ii) −x+1, −y−1, −z+1; (iii) −x+2, −y+2, −z; (iv) x, y+2, z−1; (v) x, y+1, z−1; (vi) x, y+1, z; (vii) −x+1, −y+1, −z; (viii) −x+1, −y, −z+1; (ix) −x+1, −y, −z; (x) x, y−1, z; (xi) −x+2, −y+1, −z; (xii) −x+2, −y−1, −z+1; (xiii) −x+2, −y, −z+1; (xiv) x, y−1, z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.86 | 1.83 | 2.643 (3) | 158 |
N2—H2A···O2vii | 0.86 | 2.03 | 2.856 (3) | 161 |
N2—H2B···O2 | 0.86 | 2.03 | 2.877 (3) | 167 |
N4—H4A···N3ix | 0.86 | 2.28 | 3.091 (3) | 157 |
C11—H11···O2viii | 0.93 | 2.59 | 3.477 (4) | 160 |
Symmetry codes: (vii) −x+1, −y+1, −z; (viii) −x+1, −y, −z+1; (ix) −x+1, −y, −z. |
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