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Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804020689/bt6501sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536804020689/bt65014sup2.hkl |
CCDC reference: 238053
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.035
- wR factor = 0.083
- Data-to-parameter ratio = 12.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT420_ALERT_2_C D-H Without Acceptor N3 - H031 ... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6
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 1 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 2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Fait, 1991); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.
C16H14ClN5O·C2H6O | F(000) = 784 |
Mr = 373.84 | Dx = 1.382 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.6757 (10) Å | Cell parameters from 63 reflections |
b = 7.7798 (9) Å | θ = 4.5–12.5° |
c = 21.919 (2) Å | µ = 0.24 mm−1 |
β = 99.14 (1)° | T = 173 K |
V = 1797.3 (3) Å3 | Tablet, colourless |
Z = 4 | 0.4 × 0.4 × 0.3 mm |
Siemens P4 diffractometer | Rint = 0.022 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 3.2° |
Graphite monochromator | h = −12→12 |
ω scans | k = −9→4 |
4927 measured reflections | l = 0→25 |
3167 independent reflections | 3 standard reflections every 247 reflections |
2349 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.083 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.93 | w = 1/[σ2(Fo2) + (0.0484P)2] where P = (Fo2 + 2Fc2)/3 |
3167 reflections | (Δ/σ)max = 0.001 |
260 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 6.7737 (0.0015) x + 2.0537 (0.0022) y + 13.5119 (0.0046) z = 9.4223 (0.0013) * -0.0203 (0.0014) C3 * 0.0704 (0.0015) C4 * 0.0405 (0.0015) C5 * 0.0243 (0.0015) C12 * 0.1520 (0.0015) C13 * 0.1260 (0.0015) C14 * -0.0298 (0.0015) C15 * -0.1946 (0.0016) C16 * -0.1700 (0.0016) C17 * -0.0418 (0.0014) N1 * -0.0890 (0.0013) N2 * 0.0324 (0.0014) N3 * -0.1171 (0.0012) N4 * 0.0803 (0.0014) N5 * 0.1400 (0.0011) O1 * -0.0034 (0.0008) Cl Rms deviation of fitted atoms = 0.1015 - 6.6383 (0.0052) x + 4.4211 (0.0049) y + 13.8267 (0.0091) z = 2.9976 (0.0042) Angle to previous plane (with approximate e.s.d.) = 81.55 (0.03) * -0.0056 (0.0010) N4 * -0.0037 (0.0014) C18 * 0.0061 (0.0014) C19 * 0.0040 (0.0013) C20 * -0.0108 (0.0014) C21 * 0.0017 (0.0013) C22 * 0.0084 (0.0014) C23 Rms deviation of fitted atoms = 0.0064 ============================================================================ Contacts: 3.6286 (0.0011) Cl - Cl_$5 101.82 (0.07) C15 - Cl - Cl_$5 $5 - x, -y + 2, -z + 1 |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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. |
x | y | z | Uiso*/Ueq | ||
Cl | 0.04477 (5) | 0.81766 (7) | 0.55036 (2) | 0.04214 (16) | |
O1 | 0.43047 (11) | 0.18838 (16) | 0.46327 (5) | 0.0275 (3) | |
N1 | 0.68056 (14) | 0.0993 (2) | 0.33798 (7) | 0.0285 (4) | |
H01 | 0.7241 (17) | 0.008 (3) | 0.3254 (8) | 0.033 (5)* | |
N2 | 0.67822 (13) | 0.25984 (19) | 0.31126 (6) | 0.0265 (4) | |
C3 | 0.60229 (15) | 0.3501 (2) | 0.34070 (7) | 0.0220 (4) | |
C4 | 0.55412 (15) | 0.2524 (2) | 0.38640 (7) | 0.0216 (4) | |
N3 | 0.59107 (18) | −0.0588 (2) | 0.41236 (8) | 0.0336 (4) | |
H031 | 0.638 (2) | −0.137 (3) | 0.4083 (10) | 0.047 (7)* | |
H032 | 0.5647 (19) | −0.052 (3) | 0.4476 (10) | 0.050 (7)* | |
N4 | 0.57055 (14) | 0.5226 (2) | 0.32321 (6) | 0.0240 (3) | |
H04 | 0.6374 (18) | 0.585 (2) | 0.3201 (8) | 0.030 (5)* | |
C5 | 0.60714 (16) | 0.0899 (2) | 0.38230 (7) | 0.0240 (4) | |
N5 | 0.41956 (13) | 0.4604 (2) | 0.42298 (7) | 0.0245 (3) | |
H05 | 0.4529 (17) | 0.525 (3) | 0.4001 (9) | 0.035 (6)* | |
C6 | 0.46426 (15) | 0.2960 (2) | 0.42783 (7) | 0.0219 (4) | |
C12 | 0.32742 (15) | 0.5377 (2) | 0.45327 (7) | 0.0220 (4) | |
C13 | 0.30879 (16) | 0.7143 (2) | 0.44522 (8) | 0.0262 (4) | |
H13 | 0.3569 | 0.7760 | 0.4196 | 0.031* | |
C14 | 0.22138 (16) | 0.8007 (2) | 0.47397 (8) | 0.0280 (4) | |
H14 | 0.2094 | 0.9210 | 0.4682 | 0.034* | |
C15 | 0.15153 (16) | 0.7103 (3) | 0.51121 (8) | 0.0281 (4) | |
C16 | 0.16619 (17) | 0.5353 (3) | 0.51826 (8) | 0.0309 (4) | |
H16 | 0.1159 | 0.4740 | 0.5430 | 0.037* | |
C17 | 0.25357 (16) | 0.4478 (3) | 0.48956 (8) | 0.0291 (4) | |
H17 | 0.2632 | 0.3270 | 0.4946 | 0.035* | |
C18 | 0.47317 (15) | 0.5411 (2) | 0.27066 (7) | 0.0238 (4) | |
C19 | 0.47697 (17) | 0.6765 (2) | 0.22992 (8) | 0.0296 (4) | |
H19 | 0.5442 | 0.7578 | 0.2368 | 0.036* | |
C20 | 0.38189 (18) | 0.6928 (3) | 0.17892 (8) | 0.0341 (5) | |
H20 | 0.3846 | 0.7859 | 0.1511 | 0.041* | |
C21 | 0.28401 (18) | 0.5762 (3) | 0.16814 (9) | 0.0337 (5) | |
H21 | 0.2204 | 0.5871 | 0.1328 | 0.040* | |
C22 | 0.27925 (18) | 0.4431 (3) | 0.20932 (9) | 0.0361 (5) | |
H22 | 0.2113 | 0.3630 | 0.2026 | 0.043* | |
C23 | 0.37284 (17) | 0.4255 (3) | 0.26036 (8) | 0.0307 (4) | |
H23 | 0.3685 | 0.3337 | 0.2886 | 0.037* | |
C98 | 0.52162 (19) | 0.1041 (3) | 0.16055 (9) | 0.0384 (5) | |
H98A | 0.5779 | 0.0086 | 0.1540 | 0.046* | |
H98B | 0.4420 | 0.0940 | 0.1316 | 0.046* | |
H98C | 0.5037 | 0.1003 | 0.2030 | 0.046* | |
C99 | 0.58476 (17) | 0.2714 (2) | 0.14991 (8) | 0.0319 (4) | |
H99A | 0.5936 | 0.2805 | 0.1058 | 0.038* | |
H99B | 0.5305 | 0.3675 | 0.1597 | 0.038* | |
O99 | 0.70842 (12) | 0.28640 (17) | 0.18736 (6) | 0.0300 (3) | |
H099 | 0.7003 (19) | 0.283 (3) | 0.2245 (10) | 0.043 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl | 0.0427 (3) | 0.0409 (3) | 0.0476 (3) | 0.0088 (2) | 0.0218 (2) | −0.0045 (3) |
O1 | 0.0332 (7) | 0.0255 (7) | 0.0255 (6) | 0.0013 (6) | 0.0100 (5) | 0.0066 (6) |
N1 | 0.0345 (9) | 0.0246 (9) | 0.0285 (8) | 0.0100 (7) | 0.0114 (7) | 0.0031 (7) |
N2 | 0.0312 (8) | 0.0240 (9) | 0.0258 (8) | 0.0042 (7) | 0.0093 (6) | 0.0048 (7) |
C3 | 0.0220 (8) | 0.0225 (10) | 0.0215 (8) | −0.0003 (7) | 0.0027 (7) | −0.0011 (7) |
C4 | 0.0240 (8) | 0.0210 (10) | 0.0198 (8) | −0.0007 (7) | 0.0035 (7) | 0.0003 (7) |
N3 | 0.0480 (11) | 0.0241 (10) | 0.0316 (9) | 0.0073 (9) | 0.0150 (8) | 0.0060 (8) |
N4 | 0.0255 (8) | 0.0204 (9) | 0.0268 (8) | −0.0021 (7) | 0.0066 (6) | 0.0033 (7) |
C5 | 0.0281 (9) | 0.0234 (10) | 0.0206 (8) | 0.0031 (8) | 0.0043 (7) | 0.0018 (8) |
N5 | 0.0280 (8) | 0.0234 (9) | 0.0242 (8) | −0.0001 (7) | 0.0108 (6) | 0.0042 (7) |
C6 | 0.0217 (8) | 0.0246 (10) | 0.0186 (8) | −0.0027 (8) | 0.0010 (7) | 0.0007 (8) |
C12 | 0.0213 (8) | 0.0254 (10) | 0.0197 (8) | −0.0007 (8) | 0.0041 (7) | 0.0003 (8) |
C13 | 0.0262 (9) | 0.0278 (11) | 0.0256 (9) | −0.0042 (8) | 0.0070 (7) | 0.0032 (8) |
C14 | 0.0294 (9) | 0.0226 (10) | 0.0316 (9) | 0.0018 (8) | 0.0034 (8) | 0.0015 (8) |
C15 | 0.0267 (9) | 0.0307 (12) | 0.0276 (9) | 0.0037 (8) | 0.0068 (7) | −0.0044 (9) |
C16 | 0.0304 (10) | 0.0324 (12) | 0.0323 (10) | 0.0012 (9) | 0.0127 (8) | 0.0045 (9) |
C17 | 0.0316 (10) | 0.0241 (11) | 0.0335 (10) | 0.0026 (8) | 0.0105 (8) | 0.0045 (8) |
C18 | 0.0248 (9) | 0.0238 (10) | 0.0249 (9) | 0.0042 (8) | 0.0109 (7) | 0.0004 (8) |
C19 | 0.0335 (10) | 0.0245 (10) | 0.0327 (10) | 0.0004 (8) | 0.0110 (8) | 0.0045 (9) |
C20 | 0.0448 (11) | 0.0283 (11) | 0.0312 (10) | 0.0116 (10) | 0.0118 (9) | 0.0098 (9) |
C21 | 0.0336 (11) | 0.0360 (12) | 0.0308 (10) | 0.0112 (9) | 0.0028 (8) | 0.0013 (9) |
C22 | 0.0298 (10) | 0.0404 (13) | 0.0375 (11) | −0.0038 (9) | 0.0034 (8) | 0.0039 (10) |
C23 | 0.0321 (10) | 0.0320 (12) | 0.0285 (10) | −0.0035 (9) | 0.0061 (8) | 0.0090 (9) |
C98 | 0.0408 (12) | 0.0338 (12) | 0.0400 (11) | −0.0057 (10) | 0.0045 (9) | 0.0019 (10) |
C99 | 0.0388 (11) | 0.0286 (11) | 0.0294 (10) | 0.0023 (9) | 0.0090 (8) | 0.0012 (9) |
O99 | 0.0338 (7) | 0.0310 (8) | 0.0281 (7) | −0.0050 (6) | 0.0138 (6) | −0.0002 (6) |
Cl—C15 | 1.7448 (17) | C15—C16 | 1.376 (3) |
O1—C6 | 1.234 (2) | C16—C17 | 1.384 (3) |
N1—C5 | 1.344 (2) | C16—H16 | 0.9500 |
N1—N2 | 1.378 (2) | C17—H17 | 0.9500 |
N1—H01 | 0.92 (2) | C18—C19 | 1.385 (2) |
N2—C3 | 1.316 (2) | C18—C23 | 1.390 (2) |
C3—C4 | 1.417 (2) | C19—C20 | 1.391 (3) |
C3—N4 | 1.422 (2) | C19—H19 | 0.9500 |
C4—C5 | 1.394 (2) | C20—C21 | 1.376 (3) |
C4—C6 | 1.462 (2) | C20—H20 | 0.9500 |
N3—C5 | 1.356 (2) | C21—C22 | 1.380 (3) |
N3—H031 | 0.81 (2) | C21—H21 | 0.9500 |
N3—H032 | 0.87 (2) | C22—C23 | 1.383 (2) |
N4—C18 | 1.431 (2) | C22—H22 | 0.9500 |
N4—H04 | 0.876 (19) | C23—H23 | 0.9500 |
N5—C6 | 1.363 (2) | C98—C99 | 1.501 (3) |
N5—C12 | 1.406 (2) | C98—H98A | 0.9800 |
N5—H05 | 0.83 (2) | C98—H98B | 0.9800 |
C12—C17 | 1.393 (2) | C98—H98C | 0.9800 |
C12—C13 | 1.396 (2) | C99—O99 | 1.444 (2) |
C13—C14 | 1.381 (2) | C99—H99A | 0.9900 |
C13—H13 | 0.9500 | C99—H99B | 0.9900 |
C14—C15 | 1.383 (2) | O99—H099 | 0.83 (2) |
C14—H14 | 0.9500 | ||
C5—N1—N2 | 112.53 (15) | C15—C16—C17 | 120.53 (17) |
C5—N1—H01 | 123.9 (12) | C15—C16—H16 | 119.7 |
N2—N1—H01 | 123.5 (12) | C17—C16—H16 | 119.7 |
C3—N2—N1 | 104.24 (14) | C16—C17—C12 | 119.77 (18) |
N2—C3—C4 | 112.42 (16) | C16—C17—H17 | 120.1 |
N2—C3—N4 | 120.68 (15) | C12—C17—H17 | 120.1 |
C4—C3—N4 | 126.79 (15) | C19—C18—C23 | 119.23 (16) |
C5—C4—C3 | 104.13 (14) | C19—C18—N4 | 120.23 (16) |
C5—C4—C6 | 124.33 (15) | C23—C18—N4 | 120.54 (16) |
C3—C4—C6 | 131.45 (16) | C18—C19—C20 | 119.65 (17) |
C5—N3—H031 | 117.6 (16) | C18—C19—H19 | 120.2 |
C5—N3—H032 | 117.7 (15) | C20—C19—H19 | 120.2 |
H031—N3—H032 | 116 (2) | C21—C20—C19 | 121.02 (18) |
C3—N4—C18 | 115.06 (14) | C21—C20—H20 | 119.5 |
C3—N4—H04 | 112.5 (12) | C19—C20—H20 | 119.5 |
C18—N4—H04 | 112.2 (12) | C20—C21—C22 | 119.23 (17) |
N1—C5—N3 | 122.07 (17) | C20—C21—H21 | 120.4 |
N1—C5—C4 | 106.67 (15) | C22—C21—H21 | 120.4 |
N3—C5—C4 | 131.20 (16) | C21—C22—C23 | 120.43 (18) |
C6—N5—C12 | 128.81 (15) | C21—C22—H22 | 119.8 |
C6—N5—H05 | 116.0 (14) | C23—C22—H22 | 119.8 |
C12—N5—H05 | 115.1 (14) | C22—C23—C18 | 120.41 (17) |
O1—C6—N5 | 123.50 (15) | C22—C23—H23 | 119.8 |
O1—C6—C4 | 121.29 (16) | C18—C23—H23 | 119.8 |
N5—C6—C4 | 115.19 (15) | C99—C98—H98A | 109.5 |
C17—C12—C13 | 118.93 (16) | C99—C98—H98B | 109.5 |
C17—C12—N5 | 123.83 (17) | H98A—C98—H98B | 109.5 |
C13—C12—N5 | 117.23 (15) | C99—C98—H98C | 109.5 |
C14—C13—C12 | 120.98 (16) | H98A—C98—H98C | 109.5 |
C14—C13—H13 | 119.5 | H98B—C98—H98C | 109.5 |
C12—C13—H13 | 119.5 | O99—C99—C98 | 112.00 (15) |
C13—C14—C15 | 119.24 (17) | O99—C99—H99A | 109.2 |
C13—C14—H14 | 120.4 | C98—C99—H99A | 109.2 |
C15—C14—H14 | 120.4 | O99—C99—H99B | 109.2 |
C16—C15—C14 | 120.51 (16) | C98—C99—H99B | 109.2 |
C16—C15—Cl | 119.34 (14) | H99A—C99—H99B | 107.9 |
C14—C15—Cl | 120.15 (15) | C99—O99—H099 | 109.0 (14) |
C5—N1—N2—C3 | 0.60 (19) | C6—N5—C12—C13 | 173.07 (16) |
N1—N2—C3—C4 | −0.05 (18) | C17—C12—C13—C14 | 1.8 (3) |
N1—N2—C3—N4 | −176.45 (14) | N5—C12—C13—C14 | −179.13 (15) |
N2—C3—C4—C5 | −0.47 (19) | C12—C13—C14—C15 | 0.0 (3) |
N4—C3—C4—C5 | 175.67 (16) | C13—C14—C15—C16 | −1.8 (3) |
N2—C3—C4—C6 | −177.17 (16) | C13—C14—C15—Cl | 177.60 (13) |
N4—C3—C4—C6 | −1.0 (3) | C14—C15—C16—C17 | 1.8 (3) |
N2—C3—N4—C18 | 80.3 (2) | Cl—C15—C16—C17 | −177.61 (14) |
C4—C3—N4—C18 | −95.58 (19) | C15—C16—C17—C12 | 0.1 (3) |
N2—N1—C5—N3 | 176.73 (16) | C13—C12—C17—C16 | −1.8 (3) |
N2—N1—C5—C4 | −0.90 (19) | N5—C12—C17—C16 | 179.20 (16) |
C3—C4—C5—N1 | 0.80 (18) | C3—N4—C18—C19 | −145.85 (16) |
C6—C4—C5—N1 | 177.80 (15) | C3—N4—C18—C23 | 35.1 (2) |
C3—C4—C5—N3 | −176.53 (19) | C23—C18—C19—C20 | −1.1 (3) |
C6—C4—C5—N3 | 0.5 (3) | N4—C18—C19—C20 | 179.82 (16) |
C12—N5—C6—O1 | −2.6 (3) | C18—C19—C20—C21 | −0.2 (3) |
C12—N5—C6—C4 | 175.73 (15) | C19—C20—C21—C22 | 1.2 (3) |
C5—C4—C6—O1 | 1.0 (3) | C20—C21—C22—C23 | −1.0 (3) |
C3—C4—C6—O1 | 177.11 (16) | C21—C22—C23—C18 | −0.3 (3) |
C5—C4—C6—N5 | −177.41 (15) | C19—C18—C23—C22 | 1.4 (3) |
C3—C4—C6—N5 | −1.3 (3) | N4—C18—C23—C22 | −179.59 (16) |
C6—N5—C12—C17 | −8.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H032···O1 | 0.87 (2) | 2.41 (2) | 2.914 (2) | 117.4 (18) |
N5—H05···N4 | 0.83 (2) | 2.26 (2) | 2.955 (2) | 142.0 (18) |
N1—H01···O99i | 0.92 (2) | 1.90 (2) | 2.801 (2) | 165.6 (17) |
N3—H032···O1ii | 0.87 (2) | 2.22 (2) | 2.950 (2) | 142 (2) |
N4—H04···O99iii | 0.876 (19) | 2.30 (2) | 3.163 (2) | 170.7 (17) |
O99—H099···N2 | 0.83 (2) | 1.96 (2) | 2.7928 (19) | 176 (2) |
C17—H17···O1 | 0.95 | 2.28 | 2.884 (2) | 121 |
C21—H21···O1iv | 0.95 | 2.56 | 3.494 (2) | 167 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+1, −y, −z+1; (iii) −x+3/2, y+1/2, −z+1/2; (iv) −x+1/2, y+1/2, −z+1/2. |
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