Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014985/cv2219sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014985/cv2219Isup2.hkl |
CCDC reference: 647176
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.004 Å
- R factor = 0.059
- wR factor = 0.165
- Data-to-parameter ratio = 15.5
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.92
Author Response: This problem has arisen because there is not good quality crystals and the ata collected with a R-AXIS-IV. Hence the precision of the structure is lowered. Validation issues a number of other alerts which are related to this issue. |
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 27.00 From the CIF: _diffrn_reflns_theta_full 27.00 From the CIF: _reflns_number_total 3655 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3957 Completeness (_total/calc) 92.37% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.92 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C4 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C21 H18 N4 O
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 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 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: RAXIS (Rigaku, 1996); cell refinement: RAXIS; data reduction: RAXIS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN (Molecular Structure Corporation, 1999); software used to prepare material for publication: TEXSAN.
C21H18N4O | F(000) = 720 |
Mr = 342.39 | Dx = 1.254 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 396 reflections |
a = 12.935 (3) Å | θ = 2–25.1° |
b = 7.1220 (14) Å | µ = 0.08 mm−1 |
c = 20.465 (4) Å | T = 291 K |
β = 105.88 (3)° | Prismatic, orange |
V = 1813.4 (6) Å3 | 0.20 × 0.18 × 0.17 mm |
Z = 4 |
Rigaku R-AXIS-IV diffractometer | 3655 independent reflections |
Radiation source: fine-focus sealed tube | 2472 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
Detector resolution: 0 pixels mm-1 | θmax = 27.0°, θmin = 1.7° |
Oscillation frames scans | h = 0→16 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −8→8 |
Tmin = 0.984, Tmax = 0.987 | l = −26→24 |
5958 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.059 | H-atom parameters constrained |
wR(F2) = 0.165 | w = 1/[σ2(Fo2) + (0.082P)2 + 0.249P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
3655 reflections | Δρmax = 0.29 e Å−3 |
236 parameters | Δρmin = −0.24 e Å−3 |
0 restraints | Extinction correction: SHELXL97 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0102 (18) |
Experimental. Analysis calculated for C21H18N4O1: C, 73.67; H, 5.30; N, 16.36. Found (%): C, 73.58; H, 5.26; N, 16.11. |
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. |
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 | ||
O1 | 1.34005 (14) | 0.8905 (2) | 0.12424 (9) | 0.0633 (5) | |
N1 | 1.39316 (16) | 1.3260 (2) | 0.20062 (10) | 0.0499 (5) | |
N2 | 1.42553 (15) | 1.1592 (2) | 0.17535 (10) | 0.0491 (5) | |
N3 | 1.13568 (15) | 1.1294 (2) | 0.12529 (9) | 0.0470 (5) | |
N4 | 0.96369 (15) | 0.7576 (2) | 0.05078 (10) | 0.0482 (5) | |
C1 | 1.33445 (18) | 1.0529 (3) | 0.14400 (11) | 0.0466 (5) | |
C2 | 1.24482 (18) | 1.1698 (3) | 0.14559 (11) | 0.0423 (5) | |
C3 | 1.28438 (18) | 1.3342 (3) | 0.17756 (11) | 0.0441 (5) | |
C4 | 1.2224 (2) | 1.5018 (3) | 0.18759 (13) | 0.0607 (7) | |
H4A | 1.2709 | 1.5964 | 0.2116 | 0.091* | |
H4B | 1.1735 | 1.4675 | 0.2134 | 0.091* | |
H4C | 1.1826 | 1.5500 | 0.1442 | 0.091* | |
C5 | 1.4653 (2) | 1.4871 (3) | 0.20993 (14) | 0.0649 (7) | |
H5A | 1.4338 | 1.5911 | 0.2273 | 0.097* | |
H5B | 1.4770 | 1.5210 | 0.1671 | 0.097* | |
H5C | 1.5328 | 1.4552 | 0.2415 | 0.097* | |
C6 | 1.52433 (18) | 1.0716 (3) | 0.21057 (11) | 0.0446 (5) | |
C7 | 1.56376 (19) | 1.0780 (3) | 0.28059 (12) | 0.0528 (6) | |
H7A | 1.5284 | 1.1477 | 0.3063 | 0.063* | |
C8 | 1.6556 (2) | 0.9801 (4) | 0.31174 (14) | 0.0622 (7) | |
H8A | 1.6830 | 0.9846 | 0.3587 | 0.075* | |
C9 | 1.7075 (2) | 0.8751 (4) | 0.27347 (16) | 0.0692 (8) | |
H9A | 1.7691 | 0.8076 | 0.2948 | 0.083* | |
C10 | 1.6680 (2) | 0.8704 (4) | 0.20377 (16) | 0.0701 (8) | |
H10A | 1.7033 | 0.8002 | 0.1781 | 0.084* | |
C11 | 1.5770 (2) | 0.9684 (3) | 0.17212 (14) | 0.0595 (6) | |
H11A | 1.5508 | 0.9657 | 0.1250 | 0.071* | |
C12 | 1.10228 (18) | 0.9729 (3) | 0.09698 (11) | 0.0481 (5) | |
H12A | 1.1515 | 0.8871 | 0.0889 | 0.058* | |
C13 | 0.98779 (18) | 0.9264 (3) | 0.07711 (11) | 0.0439 (5) | |
C14 | 0.9095 (2) | 1.0564 (3) | 0.08537 (13) | 0.0544 (6) | |
H14A | 0.9301 | 1.1739 | 0.1043 | 0.065* | |
C15 | 0.8048 (2) | 1.0080 (3) | 0.06554 (13) | 0.0598 (7) | |
H15A | 0.7526 | 1.0922 | 0.0708 | 0.072* | |
C16 | 0.77453 (19) | 0.8293 (3) | 0.03683 (11) | 0.0505 (6) | |
C17 | 0.85733 (19) | 0.7074 (3) | 0.03051 (11) | 0.0469 (5) | |
C18 | 0.8308 (2) | 0.5280 (3) | 0.00129 (12) | 0.0560 (6) | |
H18A | 0.8848 | 0.4478 | −0.0038 | 0.067* | |
C19 | 0.7264 (2) | 0.4724 (4) | −0.01941 (13) | 0.0654 (7) | |
H19A | 0.7096 | 0.3532 | −0.0378 | 0.078* | |
C20 | 0.6438 (2) | 0.5923 (4) | −0.01339 (14) | 0.0691 (8) | |
H20A | 0.5727 | 0.5526 | −0.0282 | 0.083* | |
C21 | 0.6669 (2) | 0.7667 (4) | 0.01404 (14) | 0.0640 (7) | |
H21A | 0.6114 | 0.8453 | 0.0178 | 0.077* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0595 (11) | 0.0411 (8) | 0.0806 (13) | 0.0016 (7) | 0.0045 (9) | −0.0197 (8) |
N1 | 0.0559 (13) | 0.0349 (9) | 0.0570 (12) | −0.0013 (8) | 0.0123 (9) | −0.0100 (8) |
N2 | 0.0492 (11) | 0.0366 (9) | 0.0568 (12) | 0.0012 (8) | 0.0062 (9) | −0.0109 (8) |
N3 | 0.0518 (12) | 0.0417 (9) | 0.0450 (11) | −0.0008 (8) | 0.0088 (9) | 0.0003 (8) |
N4 | 0.0538 (12) | 0.0412 (9) | 0.0479 (11) | −0.0019 (8) | 0.0113 (9) | −0.0008 (8) |
C1 | 0.0527 (14) | 0.0376 (10) | 0.0466 (13) | −0.0013 (9) | 0.0087 (10) | −0.0067 (9) |
C2 | 0.0475 (13) | 0.0374 (10) | 0.0395 (12) | −0.0002 (9) | 0.0076 (9) | −0.0011 (8) |
C3 | 0.0505 (14) | 0.0396 (10) | 0.0406 (12) | 0.0005 (9) | 0.0096 (10) | −0.0019 (9) |
C4 | 0.0675 (17) | 0.0477 (12) | 0.0661 (17) | 0.0059 (12) | 0.0171 (13) | −0.0126 (11) |
C5 | 0.0638 (16) | 0.0427 (12) | 0.0809 (19) | −0.0105 (12) | 0.0073 (14) | −0.0096 (12) |
C6 | 0.0446 (12) | 0.0382 (10) | 0.0501 (13) | −0.0037 (9) | 0.0116 (10) | −0.0039 (9) |
C7 | 0.0516 (14) | 0.0525 (12) | 0.0546 (15) | −0.0024 (11) | 0.0152 (11) | −0.0040 (10) |
C8 | 0.0565 (15) | 0.0646 (15) | 0.0610 (16) | −0.0019 (12) | 0.0085 (12) | 0.0054 (12) |
C9 | 0.0525 (16) | 0.0599 (15) | 0.090 (2) | 0.0081 (12) | 0.0114 (15) | 0.0088 (14) |
C10 | 0.0650 (18) | 0.0644 (15) | 0.086 (2) | 0.0132 (13) | 0.0291 (16) | −0.0068 (14) |
C11 | 0.0642 (16) | 0.0577 (14) | 0.0579 (15) | 0.0053 (12) | 0.0190 (13) | −0.0068 (11) |
C12 | 0.0508 (14) | 0.0418 (11) | 0.0491 (13) | 0.0001 (10) | 0.0090 (10) | −0.0009 (9) |
C13 | 0.0506 (13) | 0.0406 (10) | 0.0392 (12) | −0.0030 (9) | 0.0100 (10) | 0.0016 (9) |
C14 | 0.0574 (15) | 0.0419 (11) | 0.0639 (16) | −0.0014 (10) | 0.0164 (12) | −0.0083 (10) |
C15 | 0.0576 (16) | 0.0548 (13) | 0.0699 (17) | 0.0048 (12) | 0.0223 (13) | −0.0080 (12) |
C16 | 0.0526 (15) | 0.0565 (13) | 0.0441 (13) | −0.0051 (11) | 0.0160 (11) | −0.0020 (10) |
C17 | 0.0541 (15) | 0.0462 (11) | 0.0404 (12) | −0.0056 (10) | 0.0130 (10) | 0.0001 (9) |
C18 | 0.0661 (16) | 0.0485 (12) | 0.0537 (15) | −0.0081 (11) | 0.0168 (12) | −0.0076 (10) |
C19 | 0.0792 (19) | 0.0606 (15) | 0.0582 (16) | −0.0234 (14) | 0.0219 (14) | −0.0110 (12) |
C20 | 0.0599 (17) | 0.0872 (19) | 0.0617 (17) | −0.0279 (15) | 0.0190 (13) | −0.0123 (14) |
C21 | 0.0525 (16) | 0.0794 (17) | 0.0639 (17) | −0.0059 (13) | 0.0222 (13) | −0.0091 (13) |
O1—C1 | 1.234 (2) | C8—H8A | 0.9300 |
N1—C3 | 1.357 (3) | C9—C10 | 1.378 (4) |
N1—N2 | 1.404 (2) | C9—H9A | 0.9300 |
N1—C5 | 1.458 (3) | C10—C11 | 1.369 (4) |
N2—C1 | 1.400 (3) | C10—H10A | 0.9300 |
N2—C6 | 1.428 (3) | C11—H11A | 0.9300 |
N3—C12 | 1.276 (3) | C12—C13 | 1.462 (3) |
N3—C2 | 1.388 (3) | C12—H12A | 0.9300 |
N4—C13 | 1.319 (3) | C13—C14 | 1.416 (3) |
N4—C17 | 1.371 (3) | C14—C15 | 1.349 (4) |
C1—C2 | 1.435 (3) | C14—H14A | 0.9300 |
C2—C3 | 1.370 (3) | C15—C16 | 1.412 (3) |
C3—C4 | 1.484 (3) | C15—H15A | 0.9300 |
C4—H4A | 0.9600 | C16—C17 | 1.412 (3) |
C4—H4B | 0.9600 | C16—C21 | 1.414 (3) |
C4—H4C | 0.9600 | C17—C18 | 1.413 (3) |
C5—H5A | 0.9600 | C18—C19 | 1.359 (4) |
C5—H5B | 0.9600 | C18—H18A | 0.9300 |
C5—H5C | 0.9600 | C19—C20 | 1.399 (4) |
C6—C7 | 1.384 (3) | C19—H19A | 0.9300 |
C6—C11 | 1.385 (3) | C20—C21 | 1.362 (4) |
C7—C8 | 1.375 (3) | C20—H20A | 0.9300 |
C7—H7A | 0.9300 | C21—H21A | 0.9300 |
C8—C9 | 1.382 (4) | ||
C3—N1—N2 | 107.04 (16) | C10—C9—H9A | 120.0 |
C3—N1—C5 | 125.28 (18) | C8—C9—H9A | 120.0 |
N2—N1—C5 | 117.96 (19) | C11—C10—C9 | 120.3 (3) |
C1—N2—N1 | 109.14 (18) | C11—C10—H10A | 119.8 |
C1—N2—C6 | 121.35 (16) | C9—C10—H10A | 119.8 |
N1—N2—C6 | 119.97 (17) | C10—C11—C6 | 119.7 (2) |
C12—N3—C2 | 120.48 (19) | C10—C11—H11A | 120.2 |
C13—N4—C17 | 117.79 (19) | C6—C11—H11A | 120.2 |
O1—C1—N2 | 122.7 (2) | N3—C12—C13 | 121.0 (2) |
O1—C1—C2 | 132.2 (2) | N3—C12—H12A | 119.5 |
N2—C1—C2 | 105.06 (17) | C13—C12—H12A | 119.5 |
C3—C2—N3 | 122.44 (19) | N4—C13—C14 | 123.2 (2) |
C3—C2—C1 | 107.93 (19) | N4—C13—C12 | 115.4 (2) |
N3—C2—C1 | 129.40 (18) | C14—C13—C12 | 121.43 (19) |
N1—C3—C2 | 110.24 (18) | C15—C14—C13 | 119.3 (2) |
N1—C3—C4 | 122.30 (19) | C15—C14—H14A | 120.3 |
C2—C3—C4 | 127.5 (2) | C13—C14—H14A | 120.3 |
C3—C4—H4A | 109.5 | C14—C15—C16 | 119.8 (2) |
C3—C4—H4B | 109.5 | C14—C15—H15A | 120.1 |
H4A—C4—H4B | 109.5 | C16—C15—H15A | 120.1 |
C3—C4—H4C | 109.5 | C17—C16—C15 | 117.5 (2) |
H4A—C4—H4C | 109.5 | C17—C16—C21 | 118.6 (2) |
H4B—C4—H4C | 109.5 | C15—C16—C21 | 123.8 (2) |
N1—C5—H5A | 109.5 | N4—C17—C16 | 122.39 (19) |
N1—C5—H5B | 109.5 | N4—C17—C18 | 118.1 (2) |
H5A—C5—H5B | 109.5 | C16—C17—C18 | 119.5 (2) |
N1—C5—H5C | 109.5 | C19—C18—C17 | 120.1 (2) |
H5A—C5—H5C | 109.5 | C19—C18—H18A | 120.0 |
H5B—C5—H5C | 109.5 | C17—C18—H18A | 120.0 |
C7—C6—C11 | 120.4 (2) | C18—C19—C20 | 120.8 (2) |
C7—C6—N2 | 122.3 (2) | C18—C19—H19A | 119.6 |
C11—C6—N2 | 117.2 (2) | C20—C19—H19A | 119.6 |
C8—C7—C6 | 119.4 (2) | C21—C20—C19 | 120.4 (3) |
C8—C7—H7A | 120.3 | C21—C20—H20A | 119.8 |
C6—C7—H7A | 120.3 | C19—C20—H20A | 119.8 |
C7—C8—C9 | 120.3 (3) | C20—C21—C16 | 120.5 (3) |
C7—C8—H8A | 119.9 | C20—C21—H21A | 119.7 |
C9—C8—H8A | 119.9 | C16—C21—H21A | 119.7 |
C10—C9—C8 | 120.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12A···O1 | 0.93 | 2.35 | 3.029 (3) | 130 |
C19—H19A···O1i | 0.93 | 2.44 | 3.318 (3) | 159 |
Symmetry code: (i) −x+2, −y+1, −z. |
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