Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806041845/sa2014sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806041845/sa2014Isup2.hkl |
CCDC reference: 628382
Key indicators
- Single-crystal X-ray study
- T = 93 K
- Mean (C-C) = 0.003 Å
- R factor = 0.055
- wR factor = 0.146
- Data-to-parameter ratio = 11.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure.
C36H18N2O4 | F(000) = 560.00 |
Mr = 542.52 | Dx = 1.522 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54187 Å |
Hall symbol: -P 2ybc | Cell parameters from 4583 reflections |
a = 16.805 (2) Å | θ = 3.0–68.3° |
b = 3.8795 (5) Å | µ = 0.81 mm−1 |
c = 18.381 (2) Å | T = 93 K |
β = 98.953 (9)° | Block, red |
V = 1183.8 (2) Å3 | 0.20 × 0.05 × 0.04 mm |
Z = 2 |
Rigaku R-AXIS RAPID diffractometer | 1316 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.057 |
ω scans | θmax = 68.2° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −20→20 |
Tmin = 0.960, Tmax = 0.968 | k = −4→4 |
8862 measured reflections | l = −22→22 |
2107 independent reflections |
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.055 | w = 1/[σ2(Fo2) + (0.0948P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.146 | (Δ/σ)max < 0.001 |
S = 0.89 | Δρmax = 0.33 e Å−3 |
2107 reflections | Δρmin = −0.24 e Å−3 |
191 parameters |
Refinement. Refinement using reflections with F2 > -1σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
O1 | 0.31485 (8) | 0.3924 (4) | 0.18818 (6) | 0.0327 (4) | |
O2 | 0.16913 (9) | 0.9518 (4) | 0.34356 (8) | 0.0372 (4) | |
N1 | 0.23817 (10) | 0.6556 (5) | 0.26521 (9) | 0.0297 (4) | |
C1 | 0.30827 (12) | 0.4953 (6) | 0.25010 (11) | 0.0289 (5) | |
C2 | 0.37534 (12) | 0.4528 (6) | 0.31216 (11) | 0.0278 (5) | |
C3 | 0.44412 (12) | 0.2906 (6) | 0.29979 (11) | 0.0296 (5) | |
C4 | 0.50956 (12) | 0.2530 (6) | 0.35625 (12) | 0.0299 (5) | |
C5 | 0.50638 (12) | 0.3758 (5) | 0.42693 (11) | 0.0271 (5) | |
C6 | 0.43406 (12) | 0.5369 (6) | 0.44186 (11) | 0.0280 (5) | |
C7 | 0.42518 (12) | 0.6588 (6) | 0.51335 (11) | 0.0283 (5) | |
C8 | 0.35256 (12) | 0.8069 (6) | 0.52419 (11) | 0.0303 (5) | |
C9 | 0.28891 (12) | 0.8465 (6) | 0.46606 (11) | 0.0314 (5) | |
C10 | 0.29652 (12) | 0.7350 (6) | 0.39619 (12) | 0.0285 (5) | |
C11 | 0.22890 (12) | 0.7920 (6) | 0.33506 (12) | 0.0299 (5) | |
C12 | 0.36802 (12) | 0.5754 (6) | 0.38324 (11) | 0.0276 (5) | |
C13 | 0.16877 (12) | 0.6765 (6) | 0.20592 (11) | 0.0299 (5) | |
C14 | 0.17791 (12) | 0.8328 (6) | 0.13966 (11) | 0.0324 (5) | |
C15 | 0.11226 (13) | 0.8425 (6) | 0.08382 (12) | 0.0359 (6) | |
C16 | 0.03935 (13) | 0.7033 (6) | 0.09504 (12) | 0.0382 (6) | |
C17 | 0.03105 (13) | 0.5521 (6) | 0.16139 (12) | 0.0355 (6) | |
C18 | 0.09679 (12) | 0.5362 (6) | 0.21726 (12) | 0.0327 (6) | |
H3 | 0.4475 | 0.2022 | 0.2522 | 0.036* | |
H4 | 0.5570 | 0.1416 | 0.3463 | 0.036* | |
H8 | 0.3461 | 0.8827 | 0.5721 | 0.036* | |
H9 | 0.2401 | 0.9509 | 0.4747 | 0.038* | |
H14 | 0.2280 | 0.9307 | 0.1328 | 0.039* | |
H15 | 0.1173 | 0.9448 | 0.0378 | 0.043* | |
H16 | −0.0055 | 0.7119 | 0.0566 | 0.046* | |
H17 | −0.0194 | 0.4593 | 0.1688 | 0.043* | |
H18 | 0.0920 | 0.4293 | 0.2629 | 0.039* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0342 (8) | 0.0409 (11) | 0.0219 (7) | 0.0001 (7) | 0.0006 (6) | −0.0022 (7) |
O2 | 0.0344 (9) | 0.0470 (12) | 0.0288 (8) | 0.0077 (8) | 0.0008 (6) | −0.0017 (7) |
N1 | 0.0284 (10) | 0.0361 (13) | 0.0229 (9) | 0.0003 (9) | −0.0016 (7) | 0.0001 (8) |
C1 | 0.0293 (11) | 0.0303 (15) | 0.0256 (11) | −0.0044 (10) | −0.0003 (9) | 0.0018 (10) |
C2 | 0.0286 (11) | 0.0301 (15) | 0.0242 (11) | −0.0029 (10) | 0.0019 (9) | 0.0015 (10) |
C3 | 0.0348 (12) | 0.0313 (15) | 0.0217 (11) | −0.0046 (11) | 0.0013 (9) | −0.0004 (10) |
C4 | 0.0281 (11) | 0.0319 (15) | 0.0290 (11) | 0.0011 (10) | 0.0021 (9) | 0.0015 (10) |
C5 | 0.0318 (12) | 0.0238 (14) | 0.0256 (11) | −0.0031 (10) | 0.0037 (9) | 0.0014 (10) |
C6 | 0.0288 (11) | 0.0298 (15) | 0.0248 (11) | −0.0037 (10) | 0.0021 (9) | 0.0028 (10) |
C7 | 0.0308 (11) | 0.0281 (15) | 0.0251 (11) | −0.0032 (10) | 0.0021 (9) | 0.0020 (10) |
C8 | 0.0335 (12) | 0.0337 (15) | 0.0232 (11) | −0.0009 (11) | 0.0023 (9) | 0.0002 (10) |
C9 | 0.0305 (12) | 0.0339 (16) | 0.0295 (11) | 0.0027 (11) | 0.0035 (9) | 0.0015 (11) |
C10 | 0.0315 (12) | 0.0261 (15) | 0.0270 (11) | −0.0027 (10) | 0.0021 (9) | 0.0006 (10) |
C11 | 0.0291 (12) | 0.0344 (15) | 0.0253 (11) | −0.0012 (11) | 0.0014 (9) | 0.0015 (10) |
C12 | 0.0284 (11) | 0.0279 (15) | 0.0256 (11) | −0.0033 (10) | 0.0013 (9) | 0.0016 (10) |
C13 | 0.0303 (11) | 0.0319 (15) | 0.0250 (11) | 0.0041 (10) | −0.0033 (9) | −0.0014 (10) |
C14 | 0.0333 (12) | 0.0329 (15) | 0.0298 (11) | −0.0003 (11) | 0.0009 (9) | −0.0023 (10) |
C15 | 0.0422 (14) | 0.0376 (17) | 0.0255 (11) | 0.0064 (12) | −0.0017 (10) | 0.0013 (11) |
C16 | 0.0396 (13) | 0.0400 (17) | 0.0309 (12) | 0.0054 (12) | −0.0074 (10) | −0.0085 (11) |
C17 | 0.0306 (12) | 0.0383 (16) | 0.0364 (13) | 0.0020 (11) | 0.0011 (10) | −0.0054 (11) |
C18 | 0.0357 (12) | 0.0336 (16) | 0.0280 (11) | 0.0031 (11) | 0.0024 (9) | −0.0025 (10) |
O1—C1 | 1.227 (2) | C8—C9 | 1.398 (2) |
O2—C11 | 1.211 (2) | C8—H8 | 0.950 |
N1—C1 | 1.398 (2) | C9—C10 | 1.380 (3) |
N1—C11 | 1.419 (2) | C9—H9 | 0.950 |
N1—C13 | 1.469 (2) | C10—C11 | 1.485 (2) |
C1—C2 | 1.483 (2) | C10—C12 | 1.405 (3) |
C2—C3 | 1.366 (3) | C13—C14 | 1.390 (3) |
C2—C12 | 1.414 (3) | C13—C18 | 1.372 (3) |
C3—C4 | 1.397 (2) | C14—C15 | 1.385 (2) |
C3—H3 | 0.950 | C14—H14 | 0.950 |
C4—C5 | 1.393 (3) | C15—C16 | 1.383 (3) |
C4—H4 | 0.950 | C15—H15 | 0.950 |
C5—C6 | 1.431 (3) | C16—C17 | 1.380 (3) |
C5—C7i | 1.467 (2) | C16—H16 | 0.950 |
C6—C7 | 1.426 (3) | C17—C18 | 1.388 (2) |
C6—C12 | 1.429 (2) | C17—H17 | 0.950 |
C7—C8 | 1.391 (3) | C18—H18 | 0.950 |
O1···H8ii | 2.437 | H4···H3vi | 2.478 |
O1···H14iii | 2.431 | H8···O1vii | 2.437 |
O2···H17iv | 2.491 | H14···O1viii | 2.431 |
H3···H4v | 2.478 | H17···O2ix | 2.491 |
C1—N1—C11 | 124.06 (16) | C10—C9—H9 | 119.8 |
C1—N1—C13 | 118.26 (16) | C9—C10—C11 | 119.1 (2) |
C11—N1—C13 | 117.65 (17) | C9—C10—C12 | 120.10 (18) |
O1—C1—N1 | 121.96 (17) | C11—C10—C12 | 120.76 (19) |
O1—C1—C2 | 120.7 (2) | O2—C11—N1 | 121.17 (18) |
N1—C1—C2 | 117.38 (18) | O2—C11—C10 | 122.1 (2) |
C1—C2—C3 | 119.00 (19) | N1—C11—C10 | 116.76 (19) |
C1—C2—C12 | 120.57 (19) | C2—C12—C6 | 119.5 (2) |
C3—C2—C12 | 120.43 (18) | C2—C12—C10 | 120.31 (18) |
C2—C3—C4 | 120.87 (19) | C6—C12—C10 | 120.17 (19) |
C2—C3—H3 | 119.6 | N1—C13—C14 | 119.39 (19) |
C4—C3—H3 | 119.6 | N1—C13—C18 | 118.84 (18) |
C3—C4—C5 | 121.1 (2) | C14—C13—C18 | 121.77 (18) |
C3—C4—H4 | 119.4 | C13—C14—C15 | 118.5 (2) |
C5—C4—H4 | 119.4 | C13—C14—H14 | 120.8 |
C4—C5—C6 | 119.05 (18) | C15—C14—H14 | 120.8 |
C4—C5—C7i | 121.8 (2) | C14—C15—C16 | 120.0 (2) |
C6—C5—C7i | 119.14 (18) | C14—C15—H15 | 120.0 |
C5—C6—C7 | 122.37 (17) | C16—C15—H15 | 120.0 |
C5—C6—C12 | 118.96 (18) | C15—C16—C17 | 120.8 (2) |
C7—C6—C12 | 118.7 (2) | C15—C16—H16 | 119.6 |
C5i—C7—C6 | 118.48 (19) | C17—C16—H16 | 119.6 |
C5i—C7—C8 | 122.26 (19) | C16—C17—C18 | 119.6 (2) |
C6—C7—C8 | 119.27 (17) | C16—C17—H17 | 120.2 |
C7—C8—C9 | 121.33 (19) | C18—C17—H17 | 120.2 |
C7—C8—H8 | 119.3 | C13—C18—C17 | 119.3 (2) |
C9—C8—H8 | 119.3 | C13—C18—H18 | 120.4 |
C8—C9—C10 | 120.4 (2) | C17—C18—H18 | 120.4 |
C8—C9—H9 | 119.8 | ||
C1—N1—C11—O2 | 174.2 (2) | C7i—C5—C6—C7 | −1.5 (3) |
C1—N1—C11—C10 | −4.6 (3) | C7i—C5—C6—C12 | 179.0 (2) |
C11—N1—C1—O1 | −177.2 (2) | C5—C6—C7—C5i | 1.5 (3) |
C11—N1—C1—C2 | 2.8 (3) | C5—C6—C7—C8 | −178.8 (2) |
C1—N1—C13—C14 | −56.5 (3) | C5—C6—C12—C2 | 0.3 (3) |
C1—N1—C13—C18 | 122.6 (2) | C5—C6—C12—C10 | −179.5 (2) |
C13—N1—C1—O1 | 4.6 (3) | C7—C6—C12—C2 | −179.3 (2) |
C13—N1—C1—C2 | −175.4 (2) | C7—C6—C12—C10 | 0.9 (3) |
C11—N1—C13—C14 | 125.2 (2) | C12—C6—C7—C5i | −179.0 (2) |
C11—N1—C13—C18 | −55.7 (3) | C12—C6—C7—C8 | 0.8 (3) |
C13—N1—C11—O2 | −7.6 (3) | C5i—C7—C8—C9 | 178.1 (2) |
C13—N1—C11—C10 | 173.7 (2) | C6—C7—C8—C9 | −1.6 (3) |
O1—C1—C2—C3 | −1.4 (3) | C7—C8—C9—C10 | 0.7 (3) |
O1—C1—C2—C12 | 179.2 (2) | C8—C9—C10—C11 | −177.8 (2) |
N1—C1—C2—C3 | 178.6 (2) | C8—C9—C10—C12 | 1.0 (3) |
N1—C1—C2—C12 | −0.8 (3) | C9—C10—C11—O2 | 4.6 (3) |
C1—C2—C3—C4 | 178.3 (2) | C9—C10—C11—N1 | −176.7 (2) |
C1—C2—C12—C6 | −178.9 (2) | C9—C10—C12—C2 | 178.4 (2) |
C1—C2—C12—C10 | 0.9 (3) | C9—C10—C12—C6 | −1.9 (3) |
C3—C2—C12—C6 | 1.7 (3) | C11—C10—C12—C2 | −2.7 (3) |
C3—C2—C12—C10 | −178.5 (2) | C11—C10—C12—C6 | 177.0 (2) |
C12—C2—C3—C4 | −2.2 (3) | C12—C10—C11—O2 | −174.3 (2) |
C2—C3—C4—C5 | 0.7 (3) | C12—C10—C11—N1 | 4.4 (3) |
C3—C4—C5—C6 | 1.3 (3) | N1—C13—C14—C15 | 178.5 (2) |
C3—C4—C5—C7i | −179.4 (2) | N1—C13—C18—C17 | −179.5 (2) |
C4—C5—C6—C7 | 177.9 (2) | C14—C13—C18—C17 | −0.4 (3) |
C4—C5—C6—C12 | −1.7 (3) | C18—C13—C14—C15 | −0.6 (3) |
C4—C5—C7i—C6i | −177.9 (2) | C13—C14—C15—C16 | 1.0 (3) |
C4—C5—C7i—C8i | 1.9 (3) | C14—C15—C16—C17 | −0.4 (3) |
C6—C5—C7i—C6i | 1.4 (3) | C15—C16—C17—C18 | −0.7 (3) |
C6—C5—C7i—C8i | −178.8 (2) | C16—C17—C18—C13 | 1.0 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z−1/2; (iii) x, y−1, z; (iv) −x, y+1/2, −z+1/2; (v) −x+1, y+1/2, −z+1/2; (vi) −x+1, y−1/2, −z+1/2; (vii) x, −y+3/2, z+1/2; (viii) x, y+1, z; (ix) −x, y−1/2, −z+1/2. |
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