Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In the structure of the title compound, C16H18N2O4, inter­molecular N—H...O [N...O = 2.866 (3) Å] and O—H...O [O...O = 2.611 (3) Å] hydrogen bonds link mol­ecules into a two-dimensional framework. The crystal structure is further stabilized by weak inter­molecular C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806003515/lh6559sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806003515/lh6559Isup2.hkl
Contains datablock I

CCDC reference: 270414

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.056
  • wR factor = 0.150
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.02 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT351_ALERT_3_C Long C-H Bond (0.96A) C12 - H12B ... 1.12 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 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 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2003); software used to prepare material for publication: SHELXTL.

4-[(1,3-Dioxo-2-azaspiro[4.5]decan-2-yl)amino]benzoic acid top
Crystal data top
C16H18N2O4F(000) = 1280
Mr = 302.32Dx = 1.358 Mg m3
Monoclinic, C2/cCu Kα radiation, λ = 1.54178 Å
a = 18.740 (4) ÅCell parameters from 930 reflections
b = 6.1600 (12) Åθ = 12.3–43.6°
c = 25.637 (5) ŵ = 0.82 mm1
β = 92.54 (3)°T = 293 K
V = 2956.6 (10) Å3Block, colorless
Z = 80.3 × 0.2 × 0.05 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2777 independent reflections
Radiation source: fine-focus sealed tube2073 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω scansθmax = 70.1°, θmin = 3.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 2222
Tmin = 0.784, Tmax = 0.940k = 77
15719 measured reflectionsl = 3031
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.150 w = 1/[σ2(Fo2) + (0.0671P)2 + 2.2235P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2777 reflectionsΔρmax = 0.22 e Å3
200 parametersΔρmin = 0.30 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00
Special details top

Experimental. Ratio of minimum to maximum apparent transmission: 0.833802

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.13506 (9)1.1635 (3)0.73558 (7)0.0556 (5)
N20.14030 (10)1.2142 (3)0.78776 (7)0.0616 (5)
H20.17791.30200.79680.092*
O10.22834 (10)0.9273 (3)0.73393 (7)0.0801 (6)
O20.05954 (13)1.4441 (4)0.71304 (9)0.1206 (9)
O30.04721 (12)0.7383 (3)0.99221 (7)0.0932 (7)
H30.03330.64501.02170.140*
O40.00159 (11)0.5054 (3)0.93407 (7)0.0811 (6)
C20.18287 (12)1.0320 (4)0.71091 (9)0.0566 (6)
C30.16898 (11)1.0515 (3)0.65251 (9)0.0535 (5)
C40.10175 (13)1.1952 (4)0.64757 (10)0.0681 (7)
H4A0.06171.10920.63980.102*
H4B0.10071.31670.61980.102*
C50.09320 (13)1.2883 (5)0.70050 (10)0.0697 (7)
C110.15979 (15)0.8282 (4)0.62709 (10)0.0703 (7)
H11A0.20250.73100.64000.105*
H11B0.11680.75340.64050.105*
C120.15394 (17)0.8444 (5)0.56800 (10)0.0811 (8)
H12A0.15120.70090.54980.122*
H12B0.10520.94430.55810.122*
C130.21869 (16)0.9589 (5)0.54687 (11)0.0848 (8)
H13A0.20790.95060.50640.127*
H13B0.26060.86580.55680.127*
C140.22885 (16)1.1797 (5)0.57083 (11)0.0823 (8)
H14A0.27231.25080.56020.123*
H14B0.18231.26580.55900.123*
C150.23393 (13)1.1689 (4)0.63024 (10)0.0655 (6)
H15B0.23591.30740.64690.098*
H15A0.27891.07990.64430.098*
C210.11277 (10)1.0753 (4)0.82450 (9)0.0512 (5)
C220.07991 (11)0.8783 (4)0.81204 (9)0.0577 (6)
H220.07760.83200.77720.086*
C230.05473 (12)0.7499 (4)0.85147 (9)0.0591 (6)
H230.02970.62210.84220.089*
C240.06134 (11)0.8142 (4)0.90322 (9)0.0553 (5)
C250.09286 (13)1.0142 (4)0.91502 (9)0.0617 (6)
H250.09461.05690.95200.093*
C260.11778 (12)1.1428 (4)0.87621 (9)0.0609 (6)
H260.14041.28270.88420.091*
C270.03537 (13)0.6767 (4)0.94527 (9)0.0620 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0507 (9)0.0607 (11)0.0557 (11)0.0015 (9)0.0071 (8)0.0046 (9)
N20.0621 (11)0.0660 (12)0.0571 (12)0.0110 (10)0.0093 (9)0.0012 (9)
O10.0808 (12)0.0920 (13)0.0672 (11)0.0343 (11)0.0021 (9)0.0102 (9)
O20.1284 (18)0.138 (2)0.0962 (16)0.0829 (17)0.0160 (13)0.0040 (14)
O30.1299 (17)0.0919 (14)0.0573 (11)0.0404 (13)0.0000 (10)0.0070 (10)
O40.1008 (14)0.0711 (12)0.0718 (12)0.0256 (11)0.0082 (10)0.0020 (9)
C20.0531 (12)0.0538 (12)0.0631 (14)0.0038 (11)0.0053 (10)0.0081 (11)
C30.0535 (12)0.0505 (12)0.0568 (13)0.0015 (10)0.0049 (9)0.0075 (10)
C40.0602 (14)0.0758 (16)0.0679 (16)0.0105 (13)0.0007 (11)0.0086 (13)
C50.0571 (13)0.0796 (17)0.0731 (17)0.0165 (13)0.0124 (12)0.0101 (14)
C110.0843 (17)0.0554 (14)0.0715 (17)0.0070 (13)0.0058 (13)0.0034 (12)
C120.102 (2)0.0710 (17)0.0695 (17)0.0081 (16)0.0006 (15)0.0085 (14)
C130.0901 (19)0.105 (2)0.0600 (16)0.0044 (18)0.0076 (14)0.0018 (15)
C140.0786 (17)0.099 (2)0.0705 (17)0.0212 (16)0.0144 (13)0.0161 (16)
C150.0631 (14)0.0665 (15)0.0674 (15)0.0089 (12)0.0078 (11)0.0028 (12)
C210.0419 (10)0.0552 (12)0.0566 (13)0.0009 (10)0.0030 (9)0.0019 (10)
C220.0550 (12)0.0640 (13)0.0541 (13)0.0058 (11)0.0038 (10)0.0039 (11)
C230.0553 (13)0.0583 (13)0.0636 (14)0.0078 (11)0.0017 (10)0.0001 (11)
C240.0513 (12)0.0583 (13)0.0562 (13)0.0010 (11)0.0009 (10)0.0052 (10)
C250.0693 (14)0.0629 (14)0.0527 (13)0.0070 (12)0.0004 (11)0.0012 (11)
C260.0645 (14)0.0568 (13)0.0614 (14)0.0093 (12)0.0019 (11)0.0018 (11)
C270.0632 (14)0.0633 (14)0.0592 (15)0.0069 (12)0.0014 (11)0.0036 (11)
Geometric parameters (Å, º) top
N1—N21.373 (2)C12—H12A0.9999
N1—C21.382 (3)C12—H12B1.1213
N1—C51.398 (3)C13—C141.501 (4)
N2—C211.389 (3)C13—H13A1.0504
N2—H20.9107C13—H13B0.9964
O1—C21.202 (3)C14—C151.523 (3)
O2—C51.200 (3)C14—H14A0.9742
O3—C271.272 (3)C14—H14B1.0533
O3—H30.9937C15—H15B0.9545
O4—C271.257 (3)C15—H15A1.0550
C2—C31.513 (3)C21—C261.389 (3)
C3—C111.529 (3)C21—C221.392 (3)
C3—C41.540 (3)C22—C231.383 (3)
C3—C151.547 (3)C22—H220.9374
C4—C51.488 (4)C23—C241.385 (3)
C4—H4A0.9337C23—H230.9419
C4—H4B1.0326C24—C251.394 (3)
C11—C121.517 (3)C24—C271.471 (3)
C11—H11A1.0422C25—C261.370 (3)
C11—H11B1.0020C25—H250.9822
C12—C131.524 (4)C26—H260.9781
N2—N1—C2124.02 (18)C14—C13—H13A117.6
N2—N1—C5121.05 (19)C12—C13—H13A102.0
C2—N1—C5112.63 (19)C14—C13—H13B109.5
N1—N2—C21120.53 (19)C12—C13—H13B105.9
N1—N2—H2113.8H13A—C13—H13B109.8
C21—N2—H2120.0C13—C14—C15111.8 (2)
C27—O3—H3120.4C13—C14—H14A112.7
O1—C2—N1123.3 (2)C15—C14—H14A106.4
O1—C2—C3128.0 (2)C13—C14—H14B104.5
N1—C2—C3108.65 (18)C15—C14—H14B108.8
C2—C3—C11111.19 (18)H14A—C14—H14B112.7
C2—C3—C4103.38 (19)C14—C15—C3112.0 (2)
C11—C3—C4114.0 (2)C14—C15—H15B114.1
C2—C3—C15107.38 (18)C3—C15—H15B105.5
C11—C3—C15109.81 (19)C14—C15—H15A112.3
C4—C3—C15110.79 (19)C3—C15—H15A105.0
C5—C4—C3105.49 (19)H15B—C15—H15A107.3
C5—C4—H4A107.2N2—C21—C26116.9 (2)
C3—C4—H4A109.8N2—C21—C22123.8 (2)
C5—C4—H4B110.5C26—C21—C22119.4 (2)
C3—C4—H4B117.7C23—C22—C21119.5 (2)
H4A—C4—H4B105.8C23—C22—H22121.4
O2—C5—N1123.7 (3)C21—C22—H22119.0
O2—C5—C4129.2 (3)C22—C23—C24121.2 (2)
N1—C5—C4107.1 (2)C22—C23—H23118.4
C12—C11—C3111.6 (2)C24—C23—H23120.3
C12—C11—H11A112.1C23—C24—C25118.7 (2)
C3—C11—H11A108.1C23—C24—C27121.3 (2)
C12—C11—H11B110.5C25—C24—C27120.1 (2)
C3—C11—H11B110.1C26—C25—C24120.5 (2)
H11A—C11—H11B104.1C26—C25—H25123.2
C11—C12—C13111.2 (2)C24—C25—H25116.2
C11—C12—H12A114.1C25—C26—C21120.6 (2)
C13—C12—H12A105.6C25—C26—H26121.1
C11—C12—H12B106.5C21—C26—H26118.2
C13—C12—H12B108.6O4—C27—O3122.1 (2)
H12A—C12—H12B110.8O4—C27—C24119.7 (2)
C14—C13—C12111.3 (2)O3—C27—C24118.2 (2)
C2—N1—N2—C2184.6 (3)C3—C11—C12—C1356.8 (3)
C5—N1—N2—C21113.9 (2)C11—C12—C13—C1456.3 (3)
N2—N1—C2—O19.8 (3)C12—C13—C14—C1555.1 (3)
C5—N1—C2—O1172.7 (2)C13—C14—C15—C354.6 (3)
N2—N1—C2—C3168.26 (18)C2—C3—C15—C14174.9 (2)
C5—N1—C2—C35.4 (3)C11—C3—C15—C1453.8 (3)
O1—C2—C3—C1154.0 (3)C4—C3—C15—C1472.9 (3)
N1—C2—C3—C11128.0 (2)N1—N2—C21—C26177.52 (19)
O1—C2—C3—C4176.7 (2)N1—N2—C21—C221.2 (3)
N1—C2—C3—C45.3 (2)N2—C21—C22—C23179.4 (2)
O1—C2—C3—C1566.2 (3)C26—C21—C22—C232.0 (3)
N1—C2—C3—C15111.8 (2)C21—C22—C23—C240.3 (3)
C2—C3—C4—C513.2 (2)C22—C23—C24—C251.2 (3)
C11—C3—C4—C5134.1 (2)C22—C23—C24—C27179.3 (2)
C15—C3—C4—C5101.5 (2)C23—C24—C25—C261.0 (3)
N2—N1—C5—O20.2 (4)C27—C24—C25—C26179.4 (2)
C2—N1—C5—O2163.7 (3)C24—C25—C26—C210.7 (4)
N2—N1—C5—C4177.70 (19)N2—C21—C26—C25179.1 (2)
C2—N1—C5—C414.3 (3)C22—C21—C26—C252.1 (3)
C3—C4—C5—O2161.0 (3)C23—C24—C27—O45.6 (3)
C3—C4—C5—N116.8 (3)C25—C24—C27—O4174.0 (2)
C2—C3—C11—C12173.8 (2)C23—C24—C27—O3175.5 (2)
C4—C3—C11—C1269.9 (3)C25—C24—C27—O35.0 (3)
C15—C3—C11—C1255.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.912.102.866 (3)141
O3—H3···O4ii0.991.622.611 (3)171
C4—H4B···O4iii1.032.593.380 (3)133
C23—H23···O2iv0.942.413.249 (3)149
C25—H25···O30.982.412.773 (3)101
Symmetry codes: (i) x+1/2, y+1/2, z+3/2; (ii) x, y+1, z+2; (iii) x, y+1, z+3/2; (iv) x, y1, z+3/2.
 

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