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In the supramolecular structure of C
16H
15N
5O, weak C—H
O and C—H
N bonds combine to form molecular ladders, the former bonds acting as the rungs and the latter as the uprights.
Supporting information
CCDC reference: 203008
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.002 Å
- R factor = 0.041
- wR factor = 0.110
- Data-to-parameter ratio = 15.3
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
REFLT_03
From the CIF: _diffrn_reflns_theta_max 27.51
From the CIF: _reflns_number_total 3036
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 3241
Completeness (_total/calc) 93.67%
Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).
2-(Benzotriazol-1-ylmethyl)-1-phenyl-3-pyrazolidinone
top
Crystal data top
C16H15N5O | Z = 2 |
Mr = 293.33 | F(000) = 308 |
Triclinic, P1 | Dx = 1.382 Mg m−3 |
a = 6.4009 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.3596 (3) Å | Cell parameters from 3036 reflections |
c = 13.2794 (5) Å | θ = 3.0–27.5° |
α = 92.778 (1)° | µ = 0.09 mm−1 |
β = 94.382 (1)° | T = 120 K |
γ = 95.039 (3)° | Tablet, colourless |
V = 704.66 (4) Å3 | 0.36 × 0.26 × 0.10 mm |
Data collection top
Nonius KappaCCD diffractometer | 2538 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed X-ray tube | Rint = 0.050 |
Graphite monochromator | θmax = 27.5°, θmin = 3.0° |
φ scans and ω scans with κ offsets | h = −7→7 |
9646 measured reflections | k = −10→10 |
3036 independent reflections | l = −17→17 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0575P)2 + 0.1652P] where P = (Fo2 + 2Fc2)/3 |
3036 reflections | (Δ/σ)max < 0.001 |
199 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
Special details top
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm
(Fox & Holmes, 1966) which effectively corrects for absorption effects. High
redundancy data were used in the scaling program hence the 'multi-scan' code
word was used. No transmission coefficients are available from the program
(only scale factors for each frame). The scale factors in the experimental
table are calculated from the 'size' command in the SHELXL97 input
file. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.46083 (17) | 0.97118 (12) | 0.29183 (7) | 0.0188 (2) | |
N2 | 0.65163 (17) | 1.04830 (13) | 0.27855 (8) | 0.0222 (3) | |
N3 | 0.78900 (18) | 1.00706 (13) | 0.34788 (8) | 0.0241 (3) | |
C3A | 0.6864 (2) | 0.90057 (15) | 0.40813 (9) | 0.0208 (3) | |
C4 | 0.7625 (2) | 0.82226 (16) | 0.49297 (10) | 0.0257 (3) | |
C5 | 0.6180 (2) | 0.72137 (16) | 0.53663 (10) | 0.0276 (3) | |
C6 | 0.4059 (2) | 0.69693 (16) | 0.49882 (10) | 0.0263 (3) | |
C7 | 0.3287 (2) | 0.77324 (15) | 0.41609 (9) | 0.0218 (3) | |
C7A | 0.4761 (2) | 0.87677 (14) | 0.37223 (9) | 0.0187 (3) | |
C1 | 0.2764 (2) | 0.99623 (15) | 0.22680 (9) | 0.0203 (3) | |
N11 | 0.27827 (16) | 0.72806 (12) | 0.14005 (8) | 0.0188 (2) | |
C21 | 0.09810 (19) | 0.63799 (14) | 0.17436 (9) | 0.0176 (3) | |
C22 | 0.1303 (2) | 0.48582 (15) | 0.20789 (10) | 0.0218 (3) | |
C23 | −0.0315 (2) | 0.39448 (15) | 0.24759 (10) | 0.0242 (3) | |
C24 | −0.2250 (2) | 0.45464 (16) | 0.25485 (9) | 0.0231 (3) | |
C25 | −0.2565 (2) | 0.60552 (15) | 0.22169 (10) | 0.0222 (3) | |
C26 | −0.0958 (2) | 0.69801 (15) | 0.18079 (9) | 0.0199 (3) | |
N12 | 0.25576 (17) | 0.89584 (12) | 0.13512 (8) | 0.0192 (2) | |
C13 | 0.24836 (19) | 0.95018 (16) | 0.04031 (9) | 0.0217 (3) | |
O13 | 0.24812 (15) | 1.09172 (11) | 0.02140 (7) | 0.0284 (2) | |
C14 | 0.2407 (2) | 0.80448 (17) | −0.03131 (10) | 0.0273 (3) | |
C15 | 0.3325 (2) | 0.68101 (16) | 0.03570 (10) | 0.0248 (3) | |
H4 | 0.9058 | 0.8381 | 0.5188 | 0.031* | |
H5 | 0.6631 | 0.6665 | 0.5942 | 0.033* | |
H6 | 0.3126 | 0.6254 | 0.5314 | 0.032* | |
H7 | 0.1854 | 0.7568 | 0.3905 | 0.026* | |
H1A | 0.1497 | 0.9742 | 0.2640 | 0.024* | |
H1B | 0.2837 | 1.1103 | 0.2095 | 0.024* | |
H22 | 0.2633 | 0.4448 | 0.2035 | 0.026* | |
H23 | −0.0098 | 0.2905 | 0.2699 | 0.029* | |
H24 | −0.3358 | 0.3924 | 0.2825 | 0.028* | |
H25 | −0.3893 | 0.6465 | 0.2269 | 0.027* | |
H26 | −0.1188 | 0.8012 | 0.1575 | 0.024* | |
H14A | 0.3271 | 0.8259 | −0.0887 | 0.033* | |
H14B | 0.0945 | 0.7685 | −0.0578 | 0.033* | |
H15A | 0.2693 | 0.5711 | 0.0143 | 0.030* | |
H15B | 0.4869 | 0.6846 | 0.0328 | 0.030* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0209 (6) | 0.0175 (5) | 0.0175 (5) | −0.0028 (4) | 0.0033 (4) | 0.0018 (4) |
N2 | 0.0225 (6) | 0.0217 (5) | 0.0214 (5) | −0.0052 (4) | 0.0043 (4) | 0.0002 (4) |
N3 | 0.0234 (6) | 0.0266 (6) | 0.0214 (5) | −0.0034 (4) | 0.0036 (4) | −0.0010 (4) |
C3A | 0.0222 (7) | 0.0201 (6) | 0.0196 (6) | 0.0002 (5) | 0.0034 (5) | −0.0031 (5) |
C4 | 0.0275 (8) | 0.0264 (7) | 0.0226 (6) | 0.0051 (5) | −0.0019 (5) | −0.0030 (5) |
C5 | 0.0398 (9) | 0.0227 (7) | 0.0206 (6) | 0.0057 (6) | 0.0001 (6) | 0.0026 (5) |
C6 | 0.0378 (8) | 0.0204 (6) | 0.0209 (6) | −0.0014 (5) | 0.0065 (6) | 0.0024 (5) |
C7 | 0.0230 (7) | 0.0206 (6) | 0.0216 (6) | −0.0014 (5) | 0.0040 (5) | 0.0003 (5) |
C7A | 0.0235 (7) | 0.0167 (6) | 0.0160 (6) | 0.0016 (5) | 0.0033 (5) | −0.0011 (4) |
C1 | 0.0217 (7) | 0.0178 (6) | 0.0216 (6) | 0.0018 (5) | 0.0029 (5) | 0.0021 (5) |
N11 | 0.0202 (6) | 0.0142 (5) | 0.0225 (5) | 0.0008 (4) | 0.0041 (4) | 0.0023 (4) |
C21 | 0.0191 (7) | 0.0173 (6) | 0.0156 (5) | −0.0010 (4) | 0.0007 (5) | 0.0005 (4) |
C22 | 0.0189 (7) | 0.0190 (6) | 0.0277 (7) | 0.0025 (5) | 0.0010 (5) | 0.0027 (5) |
C23 | 0.0261 (7) | 0.0182 (6) | 0.0279 (7) | −0.0003 (5) | −0.0012 (5) | 0.0051 (5) |
C24 | 0.0237 (7) | 0.0242 (7) | 0.0206 (6) | −0.0045 (5) | 0.0040 (5) | 0.0022 (5) |
C25 | 0.0185 (7) | 0.0239 (6) | 0.0243 (6) | 0.0019 (5) | 0.0029 (5) | −0.0013 (5) |
C26 | 0.0211 (7) | 0.0173 (6) | 0.0213 (6) | 0.0023 (5) | 0.0001 (5) | 0.0017 (5) |
N12 | 0.0234 (6) | 0.0150 (5) | 0.0191 (5) | −0.0005 (4) | 0.0011 (4) | 0.0034 (4) |
C13 | 0.0144 (7) | 0.0290 (7) | 0.0213 (6) | −0.0017 (5) | −0.0003 (5) | 0.0078 (5) |
O13 | 0.0265 (6) | 0.0272 (5) | 0.0317 (5) | −0.0012 (4) | 0.0002 (4) | 0.0143 (4) |
C14 | 0.0250 (8) | 0.0358 (8) | 0.0200 (6) | −0.0035 (5) | 0.0024 (5) | 0.0009 (5) |
C15 | 0.0260 (7) | 0.0239 (7) | 0.0247 (7) | −0.0006 (5) | 0.0088 (5) | −0.0018 (5) |
Geometric parameters (Å, º) top
N1—N2 | 1.3579 (15) | N11—C15 | 1.4968 (16) |
N1—C7A | 1.3608 (15) | C21—C26 | 1.3862 (17) |
N1—C1 | 1.4451 (16) | C21—C22 | 1.3950 (17) |
N2—N3 | 1.3038 (16) | C22—C23 | 1.3846 (18) |
N3—C3A | 1.3821 (16) | C22—H22 | 0.9500 |
C3A—C7A | 1.388 (2) | C23—C24 | 1.385 (2) |
C3A—C4 | 1.4066 (18) | C23—H23 | 0.9500 |
C4—C5 | 1.377 (2) | C24—C25 | 1.3821 (18) |
C4—H4 | 0.9500 | C24—H24 | 0.9500 |
C5—C6 | 1.405 (2) | C25—C26 | 1.3916 (18) |
C5—H5 | 0.9500 | C25—H25 | 0.9500 |
C6—C7 | 1.3777 (18) | C26—H26 | 0.9500 |
C6—H6 | 0.9500 | N12—C13 | 1.3578 (16) |
C7—C7A | 1.4026 (17) | C13—O13 | 1.2216 (16) |
C7—H7 | 0.9500 | C13—C14 | 1.504 (2) |
C1—N12 | 1.4355 (16) | C14—C15 | 1.523 (2) |
C1—H1A | 0.9900 | C14—H14A | 0.9900 |
C1—H1B | 0.9900 | C14—H14B | 0.9900 |
N11—N12 | 1.4266 (14) | C15—H15A | 0.9900 |
N11—C21 | 1.4372 (15) | C15—H15B | 0.9900 |
| | | |
N2—N1—C7A | 110.17 (10) | C22—C21—N11 | 116.17 (11) |
N2—N1—C1 | 121.20 (10) | C23—C22—C21 | 120.03 (12) |
C7A—N1—C1 | 128.63 (11) | C23—C22—H22 | 120.0 |
N3—N2—N1 | 108.80 (10) | C21—C22—H22 | 120.0 |
N2—N3—C3A | 108.13 (11) | C22—C23—C24 | 120.05 (12) |
N3—C3A—C7A | 108.50 (11) | C22—C23—H23 | 120.0 |
N3—C3A—C4 | 130.63 (13) | C24—C23—H23 | 120.0 |
C7A—C3A—C4 | 120.88 (12) | C25—C24—C23 | 119.82 (12) |
C5—C4—C3A | 116.38 (13) | C25—C24—H24 | 120.1 |
C5—C4—H4 | 121.8 | C23—C24—H24 | 120.1 |
C3A—C4—H4 | 121.8 | C24—C25—C26 | 120.73 (12) |
C4—C5—C6 | 122.17 (12) | C24—C25—H25 | 119.6 |
C4—C5—H5 | 118.9 | C26—C25—H25 | 119.6 |
C6—C5—H5 | 118.9 | C21—C26—C25 | 119.31 (11) |
C7—C6—C5 | 122.17 (12) | C21—C26—H26 | 120.3 |
C7—C6—H6 | 118.9 | C25—C26—H26 | 120.3 |
C5—C6—H6 | 118.9 | C13—N12—N11 | 114.75 (10) |
C6—C7—C7A | 115.51 (13) | C13—N12—C1 | 125.00 (10) |
C6—C7—H7 | 122.2 | N11—N12—C1 | 119.44 (9) |
C7A—C7—H7 | 122.2 | O13—C13—N12 | 124.33 (12) |
N1—C7A—C3A | 104.40 (11) | O13—C13—C14 | 129.11 (12) |
N1—C7A—C7 | 132.70 (12) | N12—C13—C14 | 106.56 (11) |
C3A—C7A—C7 | 122.89 (12) | C13—C14—C15 | 102.40 (10) |
N12—C1—N1 | 112.86 (10) | C13—C14—H14A | 111.3 |
N12—C1—H1A | 109.0 | C15—C14—H14A | 111.3 |
N1—C1—H1A | 109.0 | C13—C14—H14B | 111.3 |
N12—C1—H1B | 109.0 | C15—C14—H14B | 111.3 |
N1—C1—H1B | 109.0 | H14A—C14—H14B | 109.2 |
H1A—C1—H1B | 107.8 | N11—C15—C14 | 104.87 (10) |
N12—N11—C21 | 113.61 (9) | N11—C15—H15A | 110.8 |
N12—N11—C15 | 102.97 (9) | C14—C15—H15A | 110.8 |
C21—N11—C15 | 115.58 (10) | N11—C15—H15B | 110.8 |
C26—C21—C22 | 120.06 (11) | C14—C15—H15B | 110.8 |
C26—C21—N11 | 123.66 (11) | H15A—C15—H15B | 108.8 |
| | | |
C7A—N1—N2—N3 | −0.19 (13) | C15—N11—C21—C22 | 78.69 (14) |
C1—N1—N2—N3 | 178.80 (10) | C26—C21—C22—C23 | 0.0 (2) |
N1—N2—N3—C3A | −0.02 (13) | N11—C21—C22—C23 | 176.35 (11) |
N2—N3—C3A—C7A | 0.23 (14) | C21—C22—C23—C24 | −0.5 (2) |
N2—N3—C3A—C4 | −179.50 (13) | C22—C23—C24—C25 | 0.5 (2) |
N3—C3A—C4—C5 | −179.74 (13) | C23—C24—C25—C26 | 0.1 (2) |
C7A—C3A—C4—C5 | 0.56 (18) | C22—C21—C26—C25 | 0.53 (18) |
C3A—C4—C5—C6 | 0.2 (2) | N11—C21—C26—C25 | −175.49 (11) |
C4—C5—C6—C7 | −0.5 (2) | C24—C25—C26—C21 | −0.6 (2) |
C5—C6—C7—C7A | 0.0 (2) | C21—N11—N12—C13 | −113.83 (11) |
N2—N1—C7A—C3A | 0.32 (13) | C15—N11—N12—C13 | 11.92 (13) |
C1—N1—C7A—C3A | −178.58 (11) | C21—N11—N12—C1 | 75.98 (13) |
N2—N1—C7A—C7 | −179.13 (12) | C15—N11—N12—C1 | −158.27 (11) |
C1—N1—C7A—C7 | 2.0 (2) | N1—C1—N12—C13 | −121.06 (13) |
N3—C3A—C7A—N1 | −0.33 (13) | N1—C1—N12—N11 | 48.05 (14) |
C4—C3A—C7A—N1 | 179.43 (11) | N11—N12—C13—O13 | −173.31 (11) |
N3—C3A—C7A—C7 | 179.19 (11) | C1—N12—C13—O13 | −3.7 (2) |
C4—C3A—C7A—C7 | −1.05 (18) | N11—N12—C13—C14 | 6.76 (14) |
C6—C7—C7A—N1 | −179.91 (13) | C1—N12—C13—C14 | 176.32 (11) |
C6—C7—C7A—C3A | 0.73 (18) | O13—C13—C14—C15 | 158.04 (13) |
N2—N1—C1—N12 | 84.60 (13) | N12—C13—C14—C15 | −22.03 (13) |
C7A—N1—C1—N12 | −96.61 (14) | N12—N11—C15—C14 | −25.12 (12) |
N12—N11—C21—C26 | 13.60 (16) | C21—N11—C15—C14 | 99.35 (12) |
C15—N11—C21—C26 | −105.15 (13) | C13—C14—C15—N11 | 28.90 (13) |
N12—N11—C21—C22 | −162.57 (10) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15B···O13i | 0.99 | 2.58 | 3.3084 (16) | 130 |
C25—H25···N11ii | 0.95 | 2.51 | 3.3530 (17) | 149 |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) x−1, y, z. |
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