2-(Benzotriazol-1-yl­methyl)-1-phenyl-3-pyrazolidinone: two weak hydrogen bonds combine to form molecular ladders

In the supramolecular structure of C₁₆H₁₅N₅O, 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.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](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

---

Computing details

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

Crystal data

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) Å^3	0.36 × 0.26 × 0.10 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0575P)^2 + 0.1652P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···O13^i	0.99	2.58	3.3084 (16)	130
C25—H25···N11^ii	0.95	2.51	3.3530 (17)	149

Symmetry codes: (i) −x+1, −y+2, −z; (ii) x−1, y, z.