Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
Conformational analyses and structural comparison of the title spiro­pyrazole­barbiturate, C19H16N4O4·C3H6O·H2O, and the related structure 3-bromo-1,4-diphenyl-1,2,7,9-tetraazaspiro­[5.4]dec-2-ene-6,8,10-trione acetone solvate [Bruno, Rotondo, Nicoló, Foti, Grassi & Risitano (2005). Acta Cryst. E61, o142-o144], are presented. Both compounds were synthesized by cyclo­addition of C-H and C-Br nitrilimines, generated in situ, starting from the same substrate [Foti, Grassi & Risitano (2005). Synlett. Submitted]. However, different experimental conditions led to products with reverse regioselectivity.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804032817/rz6024sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804032817/rz6024Isup2.hkl
Contains datablock I

CCDC reference: 262474

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.055
  • wR factor = 0.170
  • Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing .. ?
Alert level C DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.626 Test value = 0.600 DIFMX02_ALERT_1_C The minimum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.33 PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.63 e/A   3 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C24 PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........ O5 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 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 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Siemens, 1989); cell refinement: XSCANS; data reduction: XPREPW (Bruker, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XPW (Bruker, 1997); software used to prepare material for publication: PARST97 (Nardelli, 1995) and WinGX-PC (Version 1.6.4.05; Farrugia, 1999).

4-(4-Methoxyphenyl)-3-phenyl-2,4,8,10-tetraazaspiro[5.4]dec-1-ene-6,8,10-trione acetone solvate monohydrate top
Crystal data top
C19H16N4O4·C3H6O·H2OF(000) = 928
Mr = 440.45Dx = 1.298 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 61 reflections
a = 6.1539 (10) Åθ = 5.7–20.5°
b = 10.7908 (17) ŵ = 0.10 mm1
c = 34.057 (6) ÅT = 298 K
β = 94.504 (14)°Prismatic, colourless
V = 2254.6 (6) Å30.58 × 0.48 × 0.34 mm
Z = 4
Data collection top
Bruker P4
diffractometer
Rint = 0.022
ω scansθmax = 25°, θmin = 2.2°
Absorption correction: ψ scan
(North et al., 1968)
h = 16
Tmin = 0.873, Tmax = 0.964k = 1212
10362 measured reflectionsl = 4040
3815 independent reflections3 standard reflections every 197 reflections
2715 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0825P)2 + 1.0558P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.055(Δ/σ)max = 0.004
wR(F2) = 0.17Δρmax = 0.63 e Å3
S = 1.05Δρmin = 0.19 e Å3
3815 reflectionsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
297 parametersExtinction coefficient: 0.0082 (16)
0 restraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.6797 (3)0.7143 (2)0.09216 (6)0.0686 (6)
O20.2571 (3)0.4425 (2)0.02063 (6)0.0700 (6)
O30.0064 (3)0.8323 (2)0.03206 (6)0.0697 (6)
C10.5025 (4)0.6899 (3)0.07625 (7)0.0525 (7)
N20.4623 (3)0.5767 (2)0.05858 (6)0.0563 (6)
H20.56130.52080.06230.068*
C30.2785 (4)0.5455 (3)0.03557 (8)0.0552 (7)
N40.1231 (3)0.6350 (2)0.02953 (6)0.0579 (6)
H40.0060.61470.01550.069*
C50.1349 (4)0.7539 (3)0.04354 (8)0.0529 (7)
C60.3094 (4)0.7770 (2)0.07688 (7)0.0494 (6)
C70.3824 (5)0.9102 (3)0.07878 (8)0.0595 (7)
H70.44330.94930.05790.071*
N80.3547 (4)0.9653 (2)0.11101 (7)0.0562 (6)
N90.2653 (3)0.88387 (19)0.13655 (6)0.0496 (5)
C100.1973 (4)0.7664 (2)0.11719 (7)0.0451 (6)
H100.03860.76710.11160.054*
C110.1520 (4)0.9336 (2)0.16715 (8)0.0506 (6)
C120.0110 (5)0.8662 (3)0.18369 (9)0.0621 (8)
H120.04960.78820.17380.075*
C130.1150 (6)0.9143 (3)0.21460 (10)0.0747 (9)
H130.22410.86850.22530.09*
C140.0599 (6)1.0294 (3)0.23004 (10)0.0801 (10)
H140.12851.06070.25130.096*
C150.0981 (6)1.0966 (3)0.21334 (9)0.0775 (10)
H150.13341.17520.2230.093*
C160.2059 (5)1.0503 (3)0.18249 (9)0.0643 (8)
H160.31451.09680.1720.077*
C170.2602 (4)0.6541 (2)0.14201 (7)0.0448 (6)
C180.1324 (4)0.5477 (3)0.13891 (8)0.0562 (7)
H180.00460.54740.12240.067*
C190.1932 (5)0.4428 (3)0.15998 (9)0.0640 (8)
H190.10630.37230.15760.077*
C200.3833 (5)0.4418 (3)0.18469 (8)0.0580 (7)
C210.5100 (5)0.5472 (3)0.18857 (8)0.0593 (7)
H210.63670.54770.20530.071*
C220.4472 (4)0.6521 (2)0.16731 (8)0.0526 (7)
H220.53280.72310.17010.063*
O40.4295 (4)0.33269 (19)0.20402 (7)0.0783 (7)
C230.6243 (6)0.3266 (4)0.22933 (12)0.0954 (12)
H23A0.63560.24640.24160.143*
H23B0.62110.38930.24930.143*
H23C0.74770.33990.21430.143*
O60.4508 (4)0.1929 (3)0.00438 (9)0.1016 (9)
H6A0.31450.15340.00330.152*
H6B0.4110.27360.01330.152*
O50.7859 (4)0.3853 (3)0.06342 (8)0.1055 (9)
C240.7947 (6)0.2704 (5)0.08364 (12)0.0941 (12)
C250.6377 (11)0.2547 (6)0.11286 (19)0.167 (3)
H25A0.50030.22920.10010.25*
H25B0.61960.33180.12630.25*
H25C0.68920.19270.13150.25*
C260.9403 (11)0.1750 (6)0.07292 (17)0.173 (3)
H26A0.91280.15640.04540.259*
H26B0.91770.10190.08810.259*
H26C1.08810.20260.0780.259*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0349 (10)0.0963 (15)0.0727 (13)0.0060 (10)0.0066 (9)0.0200 (11)
O20.0532 (12)0.0738 (14)0.0807 (14)0.0064 (10)0.0080 (10)0.0338 (12)
O30.0610 (12)0.0781 (14)0.0670 (12)0.0164 (11)0.0131 (10)0.0059 (11)
C10.0362 (14)0.0731 (18)0.0477 (14)0.0027 (12)0.0002 (11)0.0123 (13)
N20.0355 (12)0.0699 (15)0.0621 (13)0.0079 (10)0.0045 (10)0.0193 (12)
C30.0396 (15)0.0704 (18)0.0548 (15)0.0018 (13)0.0008 (12)0.0162 (14)
N40.0385 (12)0.0717 (15)0.0610 (13)0.0050 (11)0.0121 (10)0.0224 (12)
C50.0427 (15)0.0665 (17)0.0491 (14)0.0026 (13)0.0008 (12)0.0093 (13)
C60.0382 (14)0.0609 (16)0.0485 (14)0.0021 (12)0.0003 (11)0.0103 (12)
C70.0579 (17)0.0667 (18)0.0548 (16)0.0119 (14)0.0093 (13)0.0045 (14)
N80.0557 (14)0.0551 (13)0.0587 (14)0.0117 (11)0.0101 (11)0.0052 (11)
N90.0508 (13)0.0454 (12)0.0531 (12)0.0082 (10)0.0085 (10)0.0077 (10)
C100.0337 (13)0.0517 (14)0.0496 (14)0.0036 (11)0.0007 (10)0.0102 (11)
C110.0510 (15)0.0489 (15)0.0521 (14)0.0013 (12)0.0044 (12)0.0042 (12)
C120.0593 (18)0.0575 (17)0.0714 (18)0.0068 (14)0.0163 (14)0.0115 (14)
C130.073 (2)0.074 (2)0.082 (2)0.0015 (17)0.0337 (17)0.0009 (17)
C140.103 (3)0.067 (2)0.075 (2)0.013 (2)0.035 (2)0.0078 (17)
C150.111 (3)0.0526 (17)0.072 (2)0.0004 (18)0.025 (2)0.0134 (15)
C160.083 (2)0.0500 (15)0.0619 (17)0.0090 (15)0.0162 (15)0.0082 (14)
C170.0381 (13)0.0463 (14)0.0495 (13)0.0036 (11)0.0011 (11)0.0103 (11)
C180.0469 (15)0.0560 (16)0.0641 (16)0.0088 (13)0.0052 (13)0.0064 (13)
C190.0613 (18)0.0509 (16)0.079 (2)0.0143 (14)0.0010 (15)0.0051 (15)
C200.0611 (18)0.0516 (16)0.0618 (17)0.0045 (14)0.0081 (14)0.0003 (13)
C210.0516 (16)0.0634 (18)0.0610 (16)0.0013 (14)0.0075 (13)0.0016 (14)
C220.0474 (15)0.0495 (15)0.0595 (16)0.0091 (12)0.0059 (12)0.0044 (12)
O40.0859 (16)0.0577 (12)0.0904 (16)0.0035 (11)0.0008 (13)0.0128 (11)
C230.087 (3)0.088 (3)0.110 (3)0.021 (2)0.001 (2)0.031 (2)
O60.0757 (17)0.128 (2)0.0986 (19)0.0208 (16)0.0058 (14)0.0228 (17)
O50.0818 (17)0.137 (2)0.0973 (19)0.0265 (17)0.0048 (14)0.0056 (18)
C240.071 (2)0.135 (4)0.076 (2)0.018 (2)0.0027 (19)0.036 (3)
C250.184 (6)0.149 (5)0.181 (6)0.051 (4)0.102 (5)0.037 (4)
C260.181 (6)0.204 (7)0.132 (4)0.111 (5)0.003 (4)0.004 (4)
Geometric parameters (Å, º) top
O1—C11.208 (3)C15—H150.93
O2—C31.225 (3)C16—H160.93
O3—C51.202 (3)C17—C221.383 (3)
C1—N21.376 (3)C17—C181.391 (4)
C1—C61.517 (4)C18—C191.376 (4)
N2—C31.367 (3)C18—H180.93
N2—H20.86C19—C201.386 (4)
C3—N41.364 (3)C19—H190.93
N4—C51.369 (3)C20—O41.368 (3)
N4—H40.86C20—C211.379 (4)
C5—C61.521 (3)C21—C221.382 (4)
C6—C71.506 (4)C21—H210.93
C6—C101.589 (3)C22—H220.93
C7—N81.272 (3)O4—C231.422 (4)
C7—H70.93C23—H23A0.96
N8—N91.381 (3)C23—H23B0.96
N9—C111.405 (3)C23—H23C0.96
N9—C101.475 (3)O6—H6A0.9595
C10—C171.510 (4)O6—H6B0.9595
C10—H100.98O5—C241.417 (5)
C11—C121.393 (4)C24—C261.432 (6)
C11—C161.393 (4)C24—C251.450 (6)
C12—C131.376 (4)C25—H25A0.96
C12—H120.93C25—H25B0.96
C13—C141.381 (5)C25—H25C0.96
C13—H130.93C26—H26A0.96
C14—C151.372 (5)C26—H26B0.96
C14—H140.93C26—H26C0.96
C15—C161.380 (4)
O1—C1—N2121.0 (3)C14—C15—H15119.2
O1—C1—C6122.6 (2)C16—C15—H15119.2
N2—C1—C6116.3 (2)C15—C16—C11119.9 (3)
C3—N2—C1125.6 (2)C15—C16—H16120.1
C3—N2—H2117.2C11—C16—H16120.1
C1—N2—H2117.2C22—C17—C18118.2 (2)
O2—C3—N4121.9 (2)C22—C17—C10121.7 (2)
O2—C3—N2121.3 (3)C18—C17—C10120.1 (2)
N4—C3—N2116.8 (2)C19—C18—C17120.7 (2)
C3—N4—C5126.5 (2)C19—C18—H18119.6
C3—N4—H4116.8C17—C18—H18119.6
C5—N4—H4116.8C18—C19—C20120.3 (3)
O3—C5—N4122.1 (2)C18—C19—H19119.8
O3—C5—C6122.4 (2)C20—C19—H19119.8
N4—C5—C6115.4 (2)O4—C20—C21124.7 (3)
C7—C6—C1111.2 (2)O4—C20—C19115.6 (3)
C7—C6—C5112.3 (2)C21—C20—C19119.7 (3)
C1—C6—C5113.3 (2)C20—C21—C22119.5 (2)
C7—C6—C10100.4 (2)C20—C21—H21120.3
C1—C6—C10111.2 (2)C22—C21—H21120.3
C5—C6—C10107.7 (2)C21—C22—C17121.6 (2)
N8—C7—C6115.1 (3)C21—C22—H22119.2
N8—C7—H7122.5C17—C22—H22119.2
C6—C7—H7122.5C20—O4—C23117.7 (3)
C7—N8—N9109.4 (2)O4—C23—H23A109.5
N8—N9—C11118.0 (2)O4—C23—H23B109.5
N8—N9—C10112.29 (19)H23A—C23—H23B109.5
C11—N9—C10121.3 (2)O4—C23—H23C109.5
N9—C10—C17112.84 (19)H23A—C23—H23C109.5
N9—C10—C6101.33 (19)H23B—C23—H23C109.5
C17—C10—C6115.6 (2)H6A—O6—H6B104.5
N9—C10—H10108.9O5—C24—C26120.4 (4)
C17—C10—H10108.9O5—C24—C25115.7 (4)
C6—C10—H10108.9C26—C24—C25123.7 (6)
C12—C11—C16118.6 (3)C24—C25—H25A109.5
C12—C11—N9121.0 (2)C24—C25—H25B109.5
C16—C11—N9120.4 (2)H25A—C25—H25B109.5
C13—C12—C11120.3 (3)C24—C25—H25C109.5
C13—C12—H12119.8H25A—C25—H25C109.5
C11—C12—H12119.8H25B—C25—H25C109.5
C12—C13—C14121.0 (3)C24—C26—H26A109.5
C12—C13—H13119.5C24—C26—H26B109.5
C14—C13—H13119.5H26A—C26—H26B109.5
C15—C14—C13118.6 (3)C24—C26—H26C109.5
C15—C14—H14120.7H26A—C26—H26C109.5
C13—C14—H14120.7H26B—C26—H26C109.5
C14—C15—C16121.5 (3)
O1—C1—N2—C3171.0 (3)C5—C6—C10—N9127.9 (2)
C6—C1—N2—C313.0 (4)C7—C6—C10—C17132.7 (2)
C1—N2—C3—O2179.3 (3)C1—C6—C10—C1715.0 (3)
C1—N2—C3—N40.5 (4)C5—C6—C10—C17109.7 (2)
O2—C3—N4—C5177.3 (3)N8—N9—C11—C12154.0 (2)
N2—C3—N4—C51.5 (4)C10—N9—C11—C128.3 (4)
C3—N4—C5—O3168.4 (3)N8—N9—C11—C1628.2 (4)
C3—N4—C5—C616.4 (4)C10—N9—C11—C16173.9 (2)
O1—C1—C6—C730.4 (4)C16—C11—C12—C130.2 (4)
N2—C1—C6—C7153.7 (2)N9—C11—C12—C13177.6 (3)
O1—C1—C6—C5158.0 (3)C11—C12—C13—C140.4 (5)
N2—C1—C6—C526.1 (3)C12—C13—C14—C151.4 (6)
O1—C1—C6—C1080.6 (3)C13—C14—C15—C161.8 (6)
N2—C1—C6—C1095.4 (3)C14—C15—C16—C111.2 (5)
O3—C5—C6—C730.3 (4)C12—C11—C16—C150.2 (5)
N4—C5—C6—C7154.5 (2)N9—C11—C16—C15178.0 (3)
O3—C5—C6—C1157.3 (3)N9—C10—C17—C2232.3 (3)
N4—C5—C6—C127.5 (3)C6—C10—C17—C2283.7 (3)
O3—C5—C6—C1079.3 (3)N9—C10—C17—C18149.7 (2)
N4—C5—C6—C1095.9 (3)C6—C10—C17—C1894.3 (3)
C1—C6—C7—N8111.4 (3)C22—C17—C18—C191.1 (4)
C5—C6—C7—N8120.5 (3)C10—C17—C18—C19177.0 (2)
C10—C6—C7—N86.4 (3)C17—C18—C19—C200.0 (4)
C6—C7—N8—N91.1 (3)C18—C19—C20—O4179.5 (3)
C7—N8—N9—C11157.7 (2)C18—C19—C20—C211.0 (4)
C7—N8—N9—C109.1 (3)O4—C20—C21—C22179.7 (3)
N8—N9—C10—C17136.5 (2)C19—C20—C21—C220.9 (4)
C11—N9—C10—C1776.0 (3)C20—C21—C22—C170.3 (4)
N8—N9—C10—C612.3 (3)C18—C17—C22—C211.2 (4)
C11—N9—C10—C6159.7 (2)C10—C17—C22—C21176.8 (2)
C7—C6—C10—N910.3 (2)C21—C20—O4—C231.3 (5)
C1—C6—C10—N9107.4 (2)C19—C20—O4—C23179.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···O2i0.862.052.909 (3)175
O6—H6A···O3i0.962.142.997 (3)148
C10—H10···O1ii0.982.333.280 (3)164
O6—H6B···O20.962.083.014 (4)165
N2—H2···O50.862.012.865 (4)172
Symmetry codes: (i) x, y+1, z; (ii) x1, y, z.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds