Buy article online - an online subscription or single-article purchase is required to access this article.
share
share
Issue contentsclose
Statistics
close
Download citation
closeDownload citation
Format BIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Text
Plain Text
Download PDF of article
Download PDF of articleclose
Acta Cryst. (2005). B61, 80-88
https://doi.org/10.1107/S0108768104031143
Download PDF of article
Download PDF of articleclose
Download citation
closeDownload citation
Format BIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Text
Plain Text
Statistics
close
Issue contentsclose
share
link to html

Structure determination of forms I and II of phenobarbital from X-ray powder diffraction

C. Platteau, J. Lefebvre, S. Hemon, C. Baehtz, F. Danede and D. Prevost
From pure powders of forms I and II of phenobarbital, X-ray diffraction patterns were recorded at room temperature. The starting crystal structural models were found by a Monte-Carlo simulated annealing method. The structures of the two forms were obtained through Rietveld refinements. Soft restraints were applied on bond lengths and bond angles, all H-atom positions were calculated. The cell of form I is monoclinic with the space group P21/n, Z = 12, Z′ = 3. Form II has a triclinic cell, with the space group P\bar 1, Z = 6, Z′ = 3. For both forms, the crystal cohesion is achieved by networks of N—H...O hydrogen bonds along [101]. The broadening of the Bragg peak profiles is interpreted in terms of isotropic strain effects and anisotropic size effects.
Keywords: X-ray powder diffraction; annealing method; phenobarbital.
Read articleSimilar articles

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768104031143/lc5012sup1.cif
Contains datablocks global, Phenobarbital_Form_I, Phenobarbital_Form_II

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768104031143/lc5012Isup2.rtv
Contains datablock I

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768104031143/lc5012IIsup3.rtv
Contains datablock powder

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768104031143/lc5012sup4.pdf
Geometric parameters for forms I and II of phenobarbital

CCDC references: 263169; 263170

Computing details top

For both compounds, data collection: PEAKOC; program(s) used to solve structure: FOX; program(s) used to refine structure: FULLPROF; molecular graphics: ORTEP-3; software used to prepare material for publication: SHELX97 and PARST.

Figures top
[Figure 1] Fig. 1. : Final Rietveld plot of the form I of phenobarbital. Observed data points are indicated by dots, the best fit profile (upper trace) and the difference pattern (lower trace) are solid lines. The vertical bars correspond to the position of Bragg peaks.
[Figure 2] Fig. 2. : Final Rietveld plot of the form II of phenobarbital. Same captions as Fig. 1.
[Figure 3] Fig. 3. : Atomic numbering and structure of the molecule of phenobarbital.
[Figure 4] Fig. 4. : Projection in the (a, b) plane of the unit cell of the form I of phenobarbital. Black dashed lines show the H-bonding network between molecules 1 of the asymmetric unit, blue dashed lines correspond to the H-bonding networks between molecules 2 and the red dashed are the H bonds between molecules 3 and 1 of the asymmetric unit.
[Figure 5] Fig. 5. : Projection in the (a, b) plane of the unit cell of the form II of phenobarbital. Same captions as Fig. 4.
[Figure 6] Fig. 6. : Projection in the (a, c) plane of the unit cell of the form I of phenobarbital: a) y = 0.0, b) y = 1/4, c) y = 1/2, d) y = 0.75. Same captions as Fig. 4.
[Figure 7] Fig. 7. : Projection in the (a, c) plane of the unit cell of the form II of phenobarbital: a) y = 0.0, b) y = 0.5. Same captions as Fig. 4.
[Figure 8] Fig. 8. : Average shape in the (a, c) plane of the crystallites of the form I of phenobarbital. The dotted circle indicates the average diameter.
[Figure 9] Fig. 9. : Average shape in the (a, a?b*) plane of the crystallites of the form II of phenobarbital.
(Phenobarbital_Form_I) 5-ethyl-5-phenylbarbituric acid top
Crystal data top
C12H12N2O3β = 94.1849 (8)°
Mr = 2786.83V = 3416.76 (13) Å3
Monoclinic, P21/NZ = 12
Hall symbol: -P 2ynCu Kα radiation, λ = 1.540560 Å
a = 10.6907 (2) ÅT = 293 K
b = 47.1248 (11) Å?, ? × ? × ? mm
c = 6.80017 (15) Å
Data collection top
Enraf Nonius FR 590
diffractometer		Quartz (curved monochromator)
Radiation source: sealed X-ray tubeScan method: Stationary detector
Refinement top
Rp = 3.067Profile function: pseudo-Voigt
Rwp = 4.000205 parameters
Rexp = 1.818117 restraints
RBragg = 2.822
χ2 = NOT FOUNDBackground function: linear interpolation between 29 points
3946 data pointsPreferred orientation correction: March-Dollase function, axis [0, 1, 0], G1 = 1.083 (5), G2 = 0
Excluded region(s): 0.315 to 7.0 : no Bragg peaks 80.00 to 114.720 : peak intensities too low
Crystal data top
C12H12N2O3β = 94.1849 (8)°
Mr = 2786.83V = 3416.76 (13) Å3
Monoclinic, P21/NZ = 12
a = 10.6907 (2) ÅCu Kα radiation, λ = 1.540560 Å
b = 47.1248 (11) ÅT = 293 K
c = 6.80017 (15) Å?, ? × ? × ? mm
Data collection top
Enraf Nonius FR 590
diffractometer		Scan method: Stationary detector
Refinement top
Rp = 3.067χ2 = NOT FOUND
Rwp = 4.0003946 data points
Rexp = 1.818205 parameters
RBragg = 2.822117 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Na10.1857 (14)0.2446 (2)0.641 (3)0.025 (2)*
Ca20.2828 (15)0.22915 (17)0.734 (4)0.025 (2)*
Na30.3803 (12)0.2452 (2)0.822 (3)0.025 (2)*
Ca40.3793 (15)0.27407 (18)0.848 (3)0.025 (2)*
Ca50.2697 (8)0.29083 (18)0.7446 (12)0.025 (2)*
Ca60.1656 (12)0.27325 (18)0.638 (4)0.025 (2)*
Oa20.2945 (16)0.20361 (19)0.718 (3)0.025 (2)*
Oa40.4677 (12)0.2842 (4)0.946 (2)0.025 (2)*
Oa60.0678 (11)0.2850 (3)0.587 (2)0.025 (2)*
Ha10.1182 (14)0.2328 (2)0.563 (3)0.025 (2)*
Ha30.4604 (12)0.2345 (2)0.872 (3)0.025 (2)*
Ca90.3208 (16)0.3115 (3)0.592 (3)0.025 (2)*
Ca100.2625 (16)0.3368 (3)0.530 (3)0.025 (2)*
Ca110.3065 (15)0.3570 (3)0.403 (3)0.025 (2)*
Ca120.4130 (15)0.3482 (3)0.318 (3)0.025 (2)*
Ca130.4724 (18)0.3225 (3)0.365 (3)0.025 (2)*
Ca140.4293 (14)0.3036 (3)0.501 (3)0.025 (2)*
Ha100.1782 (16)0.3407 (3)0.582 (3)0.025 (2)*
Ha110.2652 (15)0.3760 (3)0.377 (3)0.025 (2)*
Ha120.4493 (15)0.3609 (3)0.217 (3)0.025 (2)*
Ha130.5505 (18)0.3176 (3)0.297 (3)0.025 (2)*
Ha140.4736 (14)0.2851 (3)0.533 (3)0.025 (2)*
Ca70.216 (2)0.3090 (2)0.908 (2)0.025 (2)*
Ca80.1644 (18)0.2902 (4)1.064 (2)0.025 (2)*
Ha7a0.147 (2)0.3216 (2)0.849 (2)0.025 (2)*
Ha7b0.285 (2)0.3215 (2)0.972 (2)0.025 (2)*
Ha8a0.1983 (18)0.2704 (4)1.047 (2)0.025 (2)*
Ha8b0.0699 (18)0.2904 (4)1.043 (2)0.025 (2)*
Ha8c0.1931 (18)0.2982 (4)1.198 (2)0.025 (2)*
Nb10.1362 (12)0.0048 (3)0.218 (2)0.013 (2)*
Cb20.2128 (12)0.0174 (3)0.366 (3)0.013 (2)*
Nb30.3297 (11)0.0047 (3)0.385 (3)0.013 (2)*
Cb40.3719 (9)−0.0202 (3)0.311 (4)0.013 (2)*
Cb50.2703 (8)−0.03730 (18)0.1910 (12)0.013 (2)*
Cb60.1623 (13)−0.0184 (3)0.104 (2)0.013 (2)*
Ob20.1814 (14)0.0402 (2)0.430 (2)0.013 (2)*
Ob40.4818 (9)−0.0269 (4)0.330 (2)0.013 (2)*
Ob60.0840 (12)−0.0294 (4)−0.007 (2)0.013 (2)*
Hb10.0491 (12)0.0139 (3)0.189 (2)0.013 (2)*
Hb30.3966 (11)0.0160 (3)0.469 (3)0.013 (2)*
Cb90.2250 (13)−0.0587 (4)0.343 (3)0.013 (2)*
Cb100.1079 (12)−0.0586 (4)0.426 (3)0.013 (2)*
Cb110.0786 (15)−0.0783 (4)0.568 (3)0.013 (2)*
Cb120.1604 (10)−0.1010 (3)0.615 (3)0.013 (2)*
Cb130.2800 (11)−0.1002 (4)0.547 (3)0.013 (2)*
Cb140.3050 (16)−0.0817 (4)0.393 (3)0.013 (2)*
Hb100.0438 (12)−0.0437 (4)0.382 (3)0.013 (2)*
Hb11−0.0014 (15)−0.0763 (4)0.637 (3)0.013 (2)*
Hb120.1331 (10)−0.1175 (3)0.696 (3)0.013 (2)*
Hb130.3482 (11)−0.1130 (4)0.607 (3)0.013 (2)*
Hb140.3819 (16)−0.0848 (4)0.318 (3)0.013 (2)*
Cb70.3261 (19)−0.0532 (2)0.0193 (18)0.013 (2)*
Cb80.3651 (19)−0.0309 (4)−0.127 (2)0.013 (2)*
Hb7a0.2617 (19)−0.0665 (2)−0.0464 (18)0.013 (2)*
Hb7b0.4009 (19)−0.0649 (2)0.0695 (18)0.013 (2)*
Hb8a0.2937 (19)−0.0285 (4)−0.231 (2)0.013 (2)*
Hb8b0.4428 (19)−0.0381 (4)−0.187 (2)0.013 (2)*
Hb8c0.3827 (19)−0.0127 (4)−0.052 (2)0.013 (2)*
Nc10.1612 (12)0.1747 (3)0.324 (3)0.037 (2)*
Cc20.2531 (14)0.1887 (3)0.230 (4)0.037 (2)*
Nc30.3661 (12)0.1757 (2)0.209 (3)0.037 (2)*
Cc40.4012 (11)0.1485 (3)0.256 (4)0.037 (2)*
Cc50.2995 (8)0.13091 (18)0.3466 (12)0.037 (2)*
Cc60.1854 (14)0.1481 (3)0.401 (4)0.037 (2)*
Oc20.2398 (17)0.2137 (2)0.186 (3)0.037 (2)*
Oc40.5066 (9)0.1400 (4)0.234 (3)0.037 (2)*
Oc60.1015 (13)0.1365 (4)0.483 (2)0.037 (2)*
Hc10.0751 (12)0.1841 (3)0.337 (3)0.037 (2)*
Hc30.4334 (12)0.1880 (2)0.150 (3)0.037 (2)*
Cc90.2606 (14)0.1081 (4)0.192 (3)0.037 (2)*
Cc100.3407 (15)0.0870 (4)0.134 (3)0.037 (2)*
Cc110.3196 (13)0.0665 (4)−0.013 (3)0.037 (2)*
Cc120.2013 (11)0.0682 (4)−0.114 (3)0.037 (2)*
Cc130.1137 (12)0.0875 (4)−0.054 (3)0.037 (2)*
Cc140.1511 (15)0.1097 (4)0.069 (3)0.037 (2)*
Hc100.4262 (15)0.0865 (4)0.207 (3)0.037 (2)*
Hc110.3839 (13)0.0518 (4)−0.043 (3)0.037 (2)*
Hc120.1798 (11)0.0554 (4)−0.231 (3)0.037 (2)*
Hc130.0223 (12)0.0852 (4)−0.100 (3)0.037 (2)*
Hc140.0983 (15)0.1275 (4)0.069 (3)0.037 (2)*
Cc70.360 (2)0.1160 (3)0.5349 (17)0.037 (2)*
Cc80.4115 (18)0.1342 (4)0.707 (2)0.037 (2)*
Hc7a0.294 (2)0.1030 (3)0.5858 (17)0.037 (2)*
Hc7b0.431 (2)0.1038 (3)0.4932 (17)0.037 (2)*
Hc8a0.4229 (18)0.1541 (4)0.657 (2)0.037 (2)*
Hc8b0.3489 (18)0.1338 (4)0.812 (2)0.037 (2)*
Hc8c0.4944 (18)0.1258 (4)0.759 (2)0.037 (2)*
Geometric parameters (Å, º) top
Na1—Ca61.366 (13)Cb10—Hb101.01
Na1—Ca21.381 (2)Cb11—Cb121.40 (2)
Na1—Ha11.03Cb11—Hb111.01
Ca2—Oa21.216 (13)Cb12—Cb131.391 (18)
Ca2—Na31.39 (2)Cb12—Hb121.01
Na3—Ca41.370 (13)Cb13—Cb141.40 (3)
Na3—Ha31.03Cb13—Hb131.01
Ca4—Oa41.21 (2)Cb14—Hb141.01
Ca4—Ca51.539 (18)Cb7—Cb81.52 (2)
Ca5—Ca61.527 (17)Cb7—Hb7a1.01
Ca5—Ca71.546 (17)Cb7—Hb7b1.01
Ca5—Ca91.55 (2)Cb8—Hb8a1.01
Ca6—Oa61.210 (18)Cb8—Hb8b1.01
Ca9—Ca101.40 (2)Cb8—Hb8c1.01
Ca9—Ca141.40 (3)Nc1—Cc61.37 (2)
Ca10—Ca111.39 (3)Nc1—Cc21.38 (3)
Ca10—Ha101.01Nc1—Hc11.03
Ca11—Ca121.38 (3)Cc2—Oc21.222 (17)
Ca11—Ha111.01Cc2—Nc31.37 (2)
Ca12—Ca131.39 (2)Nc3—Cc41.366 (18)
Ca12—Ha121.01Nc3—Hc31.03
Ca13—Ca141.390 (3)Cc4—Oc41.215 (17)
Ca13—Ha131.01Cc4—Cc51.531 (18)
Ca14—Ha141.01Cc5—Cc61.533 (18)
Ca7—Ca81.51 (2)Cc5—Cc91.54 (2)
Ca7—Ha7a1.01Cc5—Cc71.558 (16)
Ca7—Ha7b1.01Cc6—Oc61.22 (2)
Ca8—Ha8a1.01Cc9—Cc141.39 (2)
Ca8—Ha8b1.01Cc9—Cc101.39 (3)
Ca8—Ha8c1.01Cc10—Cc111.40 (3)
Nb1—Cb61.38 (2)Cc10—Hc101.01
Nb1—Cb21.38 (2)Cc11—Cc121.394 (19)
Nb1—Hb11.03Cc11—Hc111.01
Cb2—Ob21.22 (2)Cc12—Cc131.39 (2)
Cb2—Nb31.384 (18)Cc12—Hc121.01
Nb3—Cb41.36 (2)Cc13—Cc141.38 (3)
Nb3—Hb31.03Cc13—Hc131.01
Cb4—Ob41.213 (14)Cc14—Hc141.01
Cb4—Cb51.538 (18)Cc7—Cc81.52 (2)
Cb5—Cb61.540 (16)Cc7—Hc7a1.01
Cb5—Cb71.544 (16)Cc7—Hc7b1.01
Cb6—Ob61.20 (2)Cc8—Hc8a1.01
Cb9—Cb141.40 (2)Cc8—Hc8b1.01
Cb9—Cb101.41 (2)Cc8—Hc8c1.01
Cb10—Cb111.39 (3)
Oa6···Ca13i3.37 (2)Oc2···Na3vii3.34 (2)
Ob2···Cb10ii3.42 (2)Oc2···Oa2vii3.32 (3)
Ob2···Cb11iii3.31 (2)Oc4···Ca10viii3.34 (2)
Ob4···Ob4iv3.43 (2)Oc4···Ca7viii3.44 (2)
Ob6···Cb6v3.49 (2)Oc6···Ca12ix3.23 (2)
Ob6···Ob6v3.31 (2)Oc4···Cb13iv3.23 (2)
Nc1···Oa23.24 (2)Oc6···Cb11ii3.35 (2)
Nc1···Ca14vi3.35 (2)Oc6···Cb12ii3.29 (2)
Cc2···Oa23.39 (3)Cc12···Ob2vii3.36 (2)
Oc2···Ca2vii3.23 (3)Cc13···Ob6v3.50 (2)
Ca6—Na1—Ca2129.8 (10)Cb9—Cb10—Hb10119
Ca6—Na1—Ha1115Cb10—Cb11—Cb12119.9 (16)
Ca2—Na1—Ha1115Cb10—Cb11—Hb11120
Oa2—Ca2—Na1124.1 (10)Cb12—Cb11—Hb11120
Oa2—Ca2—Na3120.0 (9)Cb13—Cb12—Cb11118.5 (12)
Na1—Ca2—Na3115.0 (15)Cb13—Cb12—Hb12121
Ca4—Na3—Ca2125.8 (9)Cb11—Cb12—Hb12121
Ca4—Na3—Ha3117Cb12—Cb13—Cb14119.6 (14)
Ca2—Na3—Ha3117Cb12—Cb13—Hb13120
Oa4—Ca4—Na3116.6 (12)Cb14—Cb13—Hb13120
Oa4—Ca4—Ca5125.9 (15)Cb13—Cb14—Cb9121.0 (16)
Na3—Ca4—Ca5117.5 (8)Cb13—Cb14—Hb14120
Ca6—Ca5—Ca4116.2 (10)Cb9—Cb14—Hb14120
Ca6—Ca5—Ca7110.3 (8)Cb8—Cb7—Cb5107.4 (11)
Ca4—Ca5—Ca7105.4 (9)Cb8—Cb7—Hb7a110
Ca6—Ca5—Ca9107.6 (9)Cb5—Cb7—Hb7a110
Ca4—Ca5—Ca9109.5 (9)Cb8—Cb7—Hb7b110
Ca7—Ca5—Ca9107.6 (10)Cb5—Cb7—Hb7b110
Oa6—Ca6—Na1125.9 (11)Hb7a—Cb7—Hb7b108
Oa6—Ca6—Ca5118.2 (12)Cb7—Cb8—Hb8a108
Na1—Ca6—Ca5114.8 (8)Cb7—Cb8—Hb8b108
Ca10—Ca9—Ca14117.2 (15)Hb8a—Cb8—Hb8b111
Ca10—Ca9—Ca5124.5 (14)Cb7—Cb8—Hb8c108
Ca14—Ca9—Ca5118.2 (15)Hb8a—Cb8—Hb8c111
Ca11—Ca10—Ca9127.6 (15)Hb8b—Cb8—Hb8c111
Ca11—Ca10—Ha10116Cc6—Nc1—Cc2119.4 (13)
Ca9—Ca10—Ha10116Cc6—Nc1—Hc1120
Ca12—Ca11—Ca10112.3 (19)Cc2—Nc1—Hc1120
Ca12—Ca11—Ha11124Oc2—Cc2—Nc3119.6 (12)
Ca10—Ca11—Ha11124Oc2—Cc2—Nc1120.1 (13)
Ca11—Ca12—Ca13122.9 (15)Nc3—Cc2—Nc1119.9 (13)
Ca11—Ca12—Ha12119Cc4—Nc3—Cc2128.5 (12)
Ca13—Ca12—Ha12119Cc4—Nc3—Hc3116
Ca14—Ca13—Ca12122.8 (14)Cc2—Nc3—Hc3116
Ca14—Ca13—Ha13119Oc4—Cc4—Nc3121.3 (12)
Ca12—Ca13—Ha13119Oc4—Cc4—Cc5124.4 (11)
Ca13—Ca14—Ca9116.7 (16)Nc3—Cc4—Cc5114.3 (10)
Ca13—Ca14—Ha14122Cc4—Cc5—Cc6114.3 (9)
Ca9—Ca14—Ha14122Cc4—Cc5—Cc9105.4 (9)
Ca8—Ca7—Ca5110.7 (11)Cc6—Cc5—Cc9110.7 (10)
Ca8—Ca7—Ha7a110Cc4—Cc5—Cc7108.2 (10)
Ca5—Ca7—Ha7a110Cc6—Cc5—Cc7109.1 (10)
Ca8—Ca7—Ha7b110Cc9—Cc5—Cc7108.8 (10)
Ca5—Ca7—Ha7b110Oc6—Cc6—Nc1117.2 (15)
Ha7a—Ca7—Ha7b108Oc6—Cc6—Cc5119.9 (14)
Ca7—Ca8—Ha8a108Nc1—Cc6—Cc5121.5 (11)
Ca7—Ca8—Ha8b108Cc14—Cc9—Cc10112.2 (15)
Ha8a—Ca8—Ha8b111Cc14—Cc9—Cc5123.2 (15)
Ca7—Ca8—Ha8c108Cc10—Cc9—Cc5123.5 (16)
Ha8a—Ca8—Ha8c111Cc9—Cc10—Cc11128.9 (18)
Ha8b—Ca8—Ha8c111Cc9—Cc10—Hc10116
Cb6—Nb1—Cb2127.9 (14)Cc11—Cc10—Hc10116
Cb6—Nb1—Hb1116Cc12—Cc11—Cc10114.0 (15)
Cb2—Nb1—Hb1116Cc12—Cc11—Hc11123
Ob2—Cb2—Nb1118.4 (16)Cc10—Cc11—Hc11123
Ob2—Cb2—Nb3128.3 (14)Cc13—Cc12—Cc11120.0 (12)
Nb1—Cb2—Nb3111.4 (12)Cc13—Cc12—Hc12120
Cb4—Nb3—Cb2131.2 (12)Cc11—Cc12—Hc12120
Cb4—Nb3—Hb3114Cc14—Cc13—Cc12120.2 (17)
Cb2—Nb3—Hb3114Cc14—Cc13—Hc13120
Ob4—Cb4—Nb3121.7 (12)Cc12—Cc13—Hc13120
Ob4—Cb4—Cb5124.2 (10)Cc13—Cc14—Cc9121.1 (16)
Nb3—Cb4—Cb5113.9 (13)Cc13—Cc14—Hc14119
Cb4—Cb5—Cb6112.4 (8)Cc9—Cc14—Hc14119
Cb4—Cb5—Cb7111.1 (10)Cc8—Cc7—Cc5118.9 (11)
Cb6—Cb5—Cb7108.1 (9)Cc8—Cc7—Hc7a107
Cb4—Cb5—Cb9103.3 (9)Cc5—Cc7—Hc7a107
Cb6—Cb5—Cb9111.7 (10)Cc8—Cc7—Hc7b107
Cb7—Cb5—Cb9110.2 (10)Cc5—Cc7—Hc7b107
Ob6—Cb6—Nb1122.3 (15)Hc7a—Cc7—Hc7b108
Ob6—Cb6—Cb5117.4 (13)Cc7—Cc8—HC8a108
Nb1—Cb6—Cb5114.8 (11)Cc7—Cc8—Hc8b108
Cb14—Cb9—Cb10116.7 (13)Hc8a—Cc8—Hc8b111
Cb14—Cb9—Cb5116.8 (14)Cc7—Cc8—Hc8c108
Cb10—Cb9—Cb5126.4 (13)Hc8a—Cc8—Hc8c111
Cb11—Cb10—Cb9121.6 (15)Hc8b—Cc8—Hc8c111
Cb11—Cb10—Hb10119
Ca6—Na1—Ca2—Oa2−175.8 (18)Cb9—Cb5—Cb6—Nb183.4 (14)
Ca6—Na1—Ca2—Na3−7 (3)Cb4—Cb5—Cb9—Cb14−75.1 (17)
Oa2—Ca2—Na3—Ca4179.6 (17)Cb6—Cb5—Cb9—Cb14163.9 (14)
Na1—Ca2—Na3—Ca410 (3)Cb7—Cb5—Cb9—Cb1443.6 (18)
Ca2—Na3—Ca4—Oa4172.5 (17)Cb4—Cb5—Cb9—Cb10109.4 (18)
Ca2—Na3—Ca4—Ca5−10 (2)Cb6—Cb5—Cb9—Cb10−12 (2)
Oa4—Ca4—Ca5—Ca6−177.0 (17)Cb7—Cb5—Cb9—Cb10−131.9 (17)
Na3—Ca4—Ca5—Ca65.5 (19)Cb14—Cb9—Cb10—Cb117 (3)
Oa4—Ca4—Ca5—Ca7−55 (2)Cb5—Cb9—Cb10—Cb11−177.5 (15)
Na3—Ca4—Ca5—Ca7127.9 (14)Cb9—Cb10—Cb11—Cb12−7 (3)
Oa4—Ca4—Ca5—Ca961 (2)Cb10—Cb11—Cb12—Cb1312 (2)
Na3—Ca4—Ca5—Ca9−116.6 (15)Cb11—Cb12—Cb13—Cb14−17 (2)
Ca2—Na1—Ca6—Oa6−164.5 (15)Cb12—Cb13—Cb14—Cb917 (3)
Ca2—Na1—Ca6—Ca53 (3)Cb10—Cb9—Cb14—Cb13−12 (3)
Ca4—Ca5—Ca6—Oa6166.4 (15)Cb5—Cb9—Cb14—Cb13172.1 (14)
Ca7—Ca5—Ca6—Oa646.6 (19)Cb4—Cb5—Cb7—Cb8−67.7 (14)
Ca9—Ca5—Ca6—Oa6−70.5 (18)Cb6—Cb5—Cb7—Cb856.1 (14)
Ca4—Ca5—Ca6—Na1−2.5 (18)Cb9—Cb5—Cb7—Cb8178.4 (12)
Ca7—Ca5—Ca6—Na1−122.2 (14)Cc6—Nc1—Cc2—Oc2169.6 (18)
Ca9—Ca5—Ca6—Na1120.6 (15)Cc6—Nc1—Cc2—Nc3−2 (3)
Ca6—Ca5—Ca9—Ca1079.3 (19)Oc2—Cc2—Nc3—Cc4−177.3 (18)
Ca4—Ca5—Ca9—Ca10−153.6 (16)Nc1—Cc2—Nc3—Cc4−6 (3)
Ca7—Ca5—Ca9—Ca10−40 (2)Cc2—Nc3—Cc4—Oc4177.8 (19)
Ca6—Ca5—Ca9—Ca14−97.1 (16)Cc2—Nc3—Cc4—Cc51 (3)
Ca4—Ca5—Ca9—Ca1430.1 (19)Oc4—Cc4—Cc5—Cc6−166.9 (17)
Ca7—Ca5—Ca9—Ca14144.1 (15)Nc3—Cc4—Cc5—Cc69.9 (19)
Ca14—Ca9—Ca10—Ca11−8 (3)Oc4—Cc4—Cc5—Cc971 (2)
Ca5—Ca9—Ca10—Ca11175.7 (16)Nc3—Cc4—Cc5—Cc9−111.9 (15)
Ca9—Ca10—Ca11—Ca128 (3)Oc4—Cc4—Cc5—Cc7−45 (2)
Ca10—Ca11—Ca12—Ca13−4 (3)Nc3—Cc4—Cc5—Cc7131.8 (14)
Ca11—Ca12—Ca13—Ca140 (3)Cc2—Nc1—Cc6—Oc6179.8 (18)
Ca12—Ca13—Ca14—Ca90 (3)Cc2—Nc1—Cc6—Cc514 (3)
Ca10—Ca9—Ca14—Ca133 (3)Cc4—Cc5—Cc6—Oc6176.7 (16)
Ca5—Ca9—Ca14—Ca13179.9 (14)Cc9—Cc5—Cc6—Oc6−64 (2)
Ca6—Ca5—Ca7—Ca863.0 (15)Cc7—Cc5—Cc6—Oc655 (2)
Ca4—Ca5—Ca7—Ca8−63.2 (15)Cc4—Cc5—Cc6—Nc1−18 (2)
Ca9—Ca5—Ca7—Ca8−179.9 (13)Cc9—Cc5—Cc6—Nc1101.3 (17)
Cb6—Nb1—Cb2—Ob2169.3 (16)Cc7—Cc5—Cc6—Nc1−138.9 (16)
Cb6—Nb1—Cb2—Nb34 (2)Cc4—Cc5—Cc9—Cc14102.5 (18)
Ob2—Cb2—Nb3—Cb4−177.4 (18)Cc6—Cc5—Cc9—Cc14−22 (2)
Nb1—Cb2—Nb3—Cb4−14 (3)Cc7—Cc5—Cc9—Cc14−141.6 (16)
Cb2—Nb3—Cb4—Ob4173.8 (17)Cc4—Cc5—Cc9—Cc10−64.6 (19)
Cb2—Nb3—Cb4—Cb5−2 (3)Cc6—Cc5—Cc9—Cc10171.3 (16)
Ob4—Cb4—Cb5—Cb6−151.0 (16)Cc7—Cc5—Cc9—Cc1051 (2)
Nb3—Cb4—Cb5—Cb624.5 (17)Cc14—Cc9—Cc10—Cc117 (3)
Ob4—Cb4—Cb5—Cb7−30 (2)Cc5—Cc9—Cc10—Cc11175.3 (16)
Nb3—Cb4—Cb5—Cb7145.8 (13)Cc9—Cc10—Cc11—Cc12−1 (3)
Ob4—Cb4—Cb5—Cb988.4 (19)Cc10—Cc11—Cc12—Cc135 (2)
Nb3—Cb4—Cb5—Cb9−96.1 (15)Cc11—Cc12—Cc13—Cc14−17 (3)
Cb2—Nb1—Cb6—Ob6172.3 (16)Cc12—Cc13—Cc14—Cc924 (3)
Cb2—Nb1—Cb6—Cb519 (2)Cc10—Cc9—Cc14—Cc13−18 (3)
Cb4—Cb5—Cb6—Ob6173.2 (14)Cc5—Cc9—Cc14—Cc13173.5 (15)
Cb7—Cb5—Cb6—Ob650.3 (16)Cc4—Cc5—Cc7—Cc8−63.2 (16)
Cb9—Cb5—Cb6—Ob6−71.2 (16)Cc6—Cc5—Cc7—Cc861.7 (17)
Cb4—Cb5—Cb6—Nb1−32.3 (16)Cc9—Cc5—Cc7—Cc8−177.3 (14)
Cb7—Cb5—Cb6—Nb1−155.2 (12)
Symmetry codes: (i) x, y, z+1; (ii) −x, −y, −z+1; (iii) −x+1, −y+1, −z; (iv) −x+1, −y, −z+1; (v) −x, −y, −z; (vi) x−1/2, −y+1/2, z−1/2; (vii) x, y, z−1; (viii) x+1/2, −y+1/2, z−1/2; (ix) x−1/2, −y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
Na1—Ha1···Oa4vi1.031.92 (2)2.93 (2)167.5 (14)
Na3—Ha3···Oa6x1.032.02 (2)2.97 (2)151.6 (13)
Nb1—Hb1···Ob6v1.031.958 (19)2.906 (19)151.6 (14)
Nb3—Hb3···Ob4iv1.031.887 (19)2.887 (19)162.9 (14)
Nc1—Hc1···Oa4xi1.032.06 (2)3.00 (2)150.4 (14)
Nc3—Hc3···Oa6xii1.031.989 (19)3.006 (19)168.9 (13)
Symmetry codes: (iv) −x+1, −y, −z+1; (v) −x, −y, −z; (vi) x−1/2, −y+1/2, z−1/2; (x) x+1/2, −y+1/2, z+1/2; (xi) −x−1/2, y+1/2, −z−1/2; (xii) −x+1/2, y+1/2, −z+3/2.
(Phenobarbital_Form_II) 5-ethyl-5-phenylbarbituric acid top
Crystal data top
C12H12N2O3β = 94.4757 (9)°
Mr = 2786.83γ = 88.1533 (12)°
Triclinic, P1V = 1705.13 (8) Å3
Hall symbol: -P 1Z = 6
a = 10.7313 (3) ÅCu Kα radiation, λ = 1.540560 Å
b = 23.5112 (7) ÅT = 293 K
c = 6.78309 (18) Å?, ? × ? × ? mm
α = 90.9687 (9)°
Data collection top
Enraf Nonius FR 590
diffractometer		Quartz (curved monochromator)
Radiation source: sealed X-ray tubeScan method: Stationary detector
Refinement top
Rp = 2.9323946 data points
Rwp = 3.771Excluded region(s): 0.315 to 7.0 : no Bragg peaks 80.00 to 114.720 : peak intensities too low
Rexp = 1.889204 parameters
RBragg = 2.410117 restraints
χ2 = NOT FOUND
Crystal data top
C12H12N2O3β = 94.4757 (9)°
Mr = 2786.83γ = 88.1533 (12)°
Triclinic, P1V = 1705.13 (8) Å3
a = 10.7313 (3) ÅZ = 6
b = 23.5112 (7) ÅCu Kα radiation, λ = 1.540560 Å
c = 6.78309 (18) ÅT = 293 K
α = 90.9687 (9)°?, ? × ? × ? mm
Data collection top
Enraf Nonius FR 590
diffractometer		Scan method: Stationary detector
Refinement top
Rp = 2.932χ2 = NOT FOUND
Rwp = 3.7713946 data points
Rexp = 1.889204 parameters
RBragg = 2.410117 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Na10.1505 (12)0.4872 (4)0.673 (3)0.007 (2)*
Ca20.2453 (13)0.4559 (4)0.768 (3)0.007 (2)*
Na30.3407 (14)0.4890 (4)0.844 (3)0.007 (2)*
Ca40.3567 (12)0.5456 (4)0.822 (4)0.007 (2)*
Ca50.2544 (8)0.5839 (4)0.7249 (12)0.007 (2)*
Ca60.1569 (13)0.5437 (4)0.634 (3)0.007 (2)*
Oa20.2463 (15)0.4045 (4)0.786 (2)0.007 (2)*
Oa40.4541 (11)0.5642 (7)0.895 (2)0.007 (2)*
Oa60.0663 (11)0.5673 (7)0.542 (2)0.007 (2)*
Ha10.0678 (12)0.4676 (4)0.631 (3)0.007 (2)*
Ha30.4097 (14)0.4674 (4)0.929 (3)0.007 (2)*
Ca90.2161 (17)0.6255 (7)0.888 (3)0.007 (2)*
Ca100.2773 (14)0.6749 (6)0.949 (3)0.007 (2)*
Ca110.2216 (12)0.7084 (8)1.090 (3)0.007 (2)*
Ca120.1030 (12)0.6992 (6)1.151 (3)0.007 (2)*
Ca130.0582 (17)0.6451 (5)1.109 (3)0.007 (2)*
Ca140.1099 (15)0.6087 (7)0.973 (3)0.007 (2)*
Ha100.3584 (14)0.6867 (6)0.898 (3)0.007 (2)*
Ha110.2683 (12)0.7411 (8)1.156 (3)0.007 (2)*
Ha120.0498 (12)0.7294 (6)1.215 (3)0.007 (2)*
Ha13−0.0101 (17)0.6295 (5)1.185 (3)0.007 (2)*
Ha140.0707 (15)0.5717 (7)0.928 (3)0.007 (2)*
Ca70.3200 (18)0.6127 (5)0.5581 (19)0.007 (2)*
Ca80.3648 (17)0.5715 (8)0.404 (2)0.007 (2)*
Ha7a0.3921 (18)0.6350 (5)0.6208 (19)0.007 (2)*
Ha7b0.2576 (18)0.6406 (5)0.4908 (19)0.007 (2)*
Ha8a0.3219 (17)0.5341 (8)0.412 (2)0.007 (2)*
Ha8b0.4582 (17)0.5663 (8)0.433 (2)0.007 (2)*
Ha8c0.3447 (17)0.5893 (8)0.270 (2)0.007 (2)*
Nb10.3322 (10)0.0097 (6)0.387 (3)0.020 (3)*
Cb20.2113 (11)0.0309 (7)0.372 (3)0.020 (3)*
Nb30.1369 (14)0.0125 (6)0.209 (2)0.020 (3)*
Cb40.1682 (15)−0.0369 (6)0.112 (3)0.020 (3)*
Cb50.2764 (8)−0.0754 (4)0.1982 (12)0.020 (3)*
Cb60.3770 (9)−0.0398 (7)0.309 (4)0.020 (3)*
Ob20.1765 (14)0.0766 (5)0.440 (2)0.020 (3)*
Ob40.0942 (13)−0.0589 (8)−0.010 (2)0.020 (3)*
Ob60.4860 (9)−0.0579 (8)0.331 (3)0.020 (3)*
Hb10.3965 (10)0.0339 (6)0.469 (3)0.020 (3)*
Hb30.0577 (14)0.0357 (6)0.160 (2)0.020 (3)*
Cb90.2248 (12)−0.1184 (7)0.339 (3)0.020 (3)*
Cb100.1113 (12)−0.1196 (7)0.426 (3)0.020 (3)*
Cb110.0808 (11)−0.1635 (7)0.548 (3)0.020 (3)*
Cb120.1779 (10)−0.2002 (8)0.620 (3)0.020 (3)*
Cb130.2923 (12)−0.1994 (9)0.536 (3)0.020 (3)*
Cb140.3131 (14)−0.1620 (7)0.387 (3)0.020 (3)*
Hb100.0477 (12)−0.0877 (7)0.398 (3)0.020 (3)*
Hb11−0.0067 (11)−0.1686 (7)0.589 (3)0.020 (3)*
Hb120.1678 (10)−0.2273 (8)0.731 (3)0.020 (3)*
Hb130.3616 (12)−0.2272 (9)0.583 (3)0.020 (3)*
Hb140.3918 (14)−0.1646 (7)0.314 (3)0.020 (3)*
Cb70.3337 (19)−0.1064 (5)0.0228 (18)0.020 (3)*
Cb80.380 (2)−0.0698 (8)−0.140 (2)0.020 (3)*
Hb7a0.2672 (19)−0.1313 (5)−0.0427 (18)0.020 (3)*
Hb7b0.4043 (19)−0.1319 (5)0.0803 (18)0.020 (3)*
Hb8a0.308 (2)−0.0577 (8)−0.236 (2)0.020 (3)*
Hb8b0.442 (2)−0.0951 (8)−0.209 (2)0.020 (3)*
Hb8c0.422 (2)−0.0357 (8)−0.076 (2)0.020 (3)*
Nc10.1507 (14)0.3514 (4)0.372 (3)0.049 (3)*
Cc20.2420 (15)0.3817 (6)0.289 (5)0.049 (3)*
Nc30.3500 (14)0.3539 (5)0.238 (3)0.049 (3)*
Cc40.3843 (12)0.2979 (5)0.275 (4)0.049 (3)*
Cc50.2830 (8)0.2635 (4)0.3613 (12)0.049 (3)*
Cc60.1599 (16)0.2940 (5)0.413 (4)0.049 (3)*
Oc20.2118 (16)0.4300 (5)0.239 (3)0.049 (3)*
Oc40.4841 (12)0.2738 (8)0.248 (3)0.049 (3)*
Oc60.0820 (14)0.2719 (8)0.506 (2)0.049 (3)*
Hc10.0684 (14)0.3728 (4)0.399 (3)0.049 (3)*
Hc30.4104 (14)0.3768 (5)0.163 (3)0.049 (3)*
Cc90.2487 (13)0.2152 (8)0.211 (3)0.049 (3)*
Cc100.3283 (16)0.1715 (8)0.151 (3)0.049 (3)*
Cc110.2952 (12)0.1362 (9)−0.009 (3)0.049 (3)*
Cc120.1763 (11)0.1380 (9)−0.113 (3)0.049 (3)*
Cc130.0992 (14)0.1810 (9)−0.040 (3)0.049 (3)*
Cc140.1331 (14)0.2217 (9)0.105 (3)0.049 (3)*
Hc100.4173 (16)0.1692 (8)0.211 (3)0.049 (3)*
Hc110.3549 (12)0.1039 (9)−0.040 (3)0.049 (3)*
Hc120.1529 (11)0.1149 (9)−0.236 (3)0.049 (3)*
Hc130.0064 (14)0.1782 (9)−0.075 (3)0.049 (3)*
Hc140.0830 (14)0.2587 (9)0.113 (3)0.049 (3)*
Cc70.329 (2)0.2325 (5)0.5555 (17)0.049 (3)*
Cc80.386 (2)0.2699 (9)0.724 (3)0.049 (3)*
Hc7a0.392 (2)0.2020 (5)0.5234 (17)0.049 (3)*
Hc7b0.254 (2)0.2132 (5)0.6027 (17)0.049 (3)*
Hc8a0.466 (2)0.2501 (9)0.779 (3)0.049 (3)*
Hc8b0.324 (2)0.2738 (9)0.827 (3)0.049 (3)*
Hc8c0.404 (2)0.3083 (9)0.669 (3)0.049 (3)*
Geometric parameters (Å, º) top
Na1—Ca21.36 (2)Cb7—Hb7b1.01
Na1—Ca61.364 (14)Cb8—Hb8a1.01
Na1—Ha11.03Cb8—Hb8b1.01
Ca2—Na31.370 (19)Cb8—Hb8c1.01
Ca2—Oa21.217 (13)Cb9—Cb101.39 (2)
Na3—Ca41.357 (14)Cb9—Cb41.40 (2)
Na3—Ha31.03Cb10—Cb111.40 (3)
Ca4—Cai51.516 (16)Cb10—Hb101.01
Ca4—Oa41.211 (19)Cb11—Cb121.39 (2)
Ca5—Ca61.519 (15)Cb11—Hb111.01
Ca5—Ca71.554 (18)Cb12—Cb131.39 (2)
Ca5—Ca91.54 (2)Cb12—Hb121.01
Ca6—Oa61.234 (19)Cb13—Cb141.39 (3)
Ca7—Ca81.51 (2)Cb13—Hb131.01
Ca7—Ha7a1.01Cb14—Hb141.01
Ca7—Ha7b1.01Nc1—Cc21.39 (3)
Ca8—Ha8a1.01Nc1—Cc61.381 (17)
Ca8—Ha8b1.01Nc1—Hc11.03
Ca8—Ha8c1.01Cc2—Nc31.38 (2)
Ca9—Ca101.39 (2)Cc2—Oc21.217 (19)
Ca9—Ca141.39 (3)Nc3—Cc41.375 (17)
Ca10—Ca111.39 (2)Nc3—Hc31.03
Ca10—Ha101.01Cc4—Cc51.53 (2)
Ca11—Ca121.39 (2)Cc4—Oc41.22 (2)
Ca11—Ha111.01Cc5—Cc61.54 (2)
Ca12—Ca131.393 (19)Cc5—Cc71.554 (15)
Ca12—Ha121.01Cc5—Cc91.55 (2)
Ca13—Ca141.39 (2)Cc6—Oc61.22 (3)
Ca13—Ha131.01Cc7—Cc81.53 (2)
Ca14—Ha141.01Cc7—Hc7a1.01
Nb1—Cb21.372 (17)Cc7—Hc7b1.01
Nb1—Cb61.36 (2)Cc8—Hc8a1.01
Nb1—Hb11.03Cc8—Hc8b1.01
Cb2—Nb31.38 (2)Cc8—Hc8c1.01
Cbi2—Ob21.22 (2)Cc9—Cc101.39 (3)
Nbi3—Cb41.37 (2)Cc9—Cc141.39 (2)
Nb3—Hb31.03Cc10—Cc111.38 (3)
Cb4—Cb51.533 (17)Cc10—Hc101.01
Cb4—Ob41.22 (2)Cc11—Cc121.41 (2)
Cb5—Cb61.529 (18)Cc11—Hc111.01
Cb5—Cb71.542 (17)Cc12—Cc131.40 (3)
Cb5—Cb91.55 (2)Cc12—Hc121.01
Cb6—Ob61.230 (15)Cc13—Cc141.40 (3)
Cb7—Cb81.54 (2)Cc13—Hc131.01
Cb7—Hb7a1.01Cc14—Hc141.01
Oa6···Ca13i3.48 (2)Oc2···Oa2i3.17 (2)
Ob2···Cb10ii3.41 (2)Oc2···Oa6iv3.43 (2)
Ob2···Cb11ii3.39 (2)Oc4···Ca10v3.25 (2)
Ob4···Ob4iii3.38 (2)Oc6···Ca12vi3.22 (2)
Nc1···Oa23.16 (2)Cc8···Oa23.49 (2)
Cc2···Oa23.40 (3)Cc14···Ca12iv3.47 (2)
Cc2···Oa2i3.47 (3)Oc4···Cb13vii3.20 (2)
Nc3···Oa2i3.40 (3)Oc6···Cb11ii3.14 (2)
Oc2···Na13.32 (2)Oc6···Cb12ii3.35 (2)
Oc2···Ca2i3.31 (3)Cc12···Ob2i3.34 (3)
Oc2···Na3i3.44 (2)
Ca2—Na1—Ca6123.8 (10)Hb7a—Cb7—Hb7b108
Ca2—Na1—Ha1119Cb7—Cb8—Hb8a110
Ca6—Na1—Ha1118Cb7—Cb8—Hb8b105
Na1—Ca2—Na3112.3 (14)Cb7—Cb8—Hb8c108
Na1—Ca2—Oa2124.7 (10)Hb8a—Cb8—Hb8b111
Na3—Ca2—Oa2123.0 (10)Hb8a—Cb8—Hb8c111
Ca2—Na3—Ca4129.4 (10)Hb8b—Cb8—Hb8c111
Ca2—Na3—Ha3114Cb5—Cb9—Cb10131.7 (13)
Ca4—Na3—Ha3116Cb5—Cb9—Cb14110.9 (14)
Na3—Ca4—Ca5121.5 (9)Cb10—Cb9—Cb14117.4 (13)
Na3—Ca4—Oa4116.6 (12)Cb9—Cb10—Cb11123.1 (14)
Ca5—Ca4—Oa4121.9 (13)Cb9—Cb10—Hb10119
Ca4—Ca5—Ca6105.1 (9)Cb11—Cb10—Hb10118
Ca4—Ca5—Ca7103.4 (9)Cb10—Cb11—Cb12117.2 (16)
Ca4—Ca5—Ca9105.5 (9)Cb10—Cb11—Hb11123
Ca6—Ca5—Ca7109.6 (9)Cb12—Cb11—Hb11120
Ca6—Ca5—Ca9118.1 (10)Cb11—Cb12—Cb13119.1 (11)
Ca7—Ca5—Ca9113.5 (10)Cb11—Cb12—Hb12122
Na1—Ca6—Ca5126.1 (9)Cb13—Cb12—Hb12119
Na1—Ca6—Oa6118.1 (12)Cb2—Cb13—Cb14121.7 (14)
Ca5—Ca6—Oa6114.7 (13)Cb12—Cb13—Hb13119
Ca5—Ca7—Ca8113.9 (11)Cb14—Cb13—Hb13119
Ca5—Ca7—Ha7a108Cb9—Cb14—Cb13119.3 (16)
Ca5—Ca7—Ha7b108Cb9—Cb14—Hb14119
Ca8—Ca7—Ha7a110Cb13—Cb14—Hb14122
Ca8—Ca7—Ha7b108Cc2—Nc1—Cc6124.7 (12)
Ha7a—Ca7—Ha7b108Cc2—Nc1—Hc1118
Ca7—Ca8—Ha8a110Cc6—Nc1—Hc1118
Ca7—Ca8—Ha8b106Nc1—Cc2—Nc3119.6 (15)
Ca7—Ca8—Ha8c108Nc1—Cc2—Oc2115.9 (13)
Ha8a—Ca8—Ha8b111Nc3—Cc2—Oc2123.5 (14)
Ha8a—Ca8—Ha8c111Cc2—Nc3—Cc4126.5 (12)
Ha8b—Ca8—Ha8c111Cc2—Nc3—Hc3117
Ca5—Ca9—Ca10126.1 (15)Cc4—Nc3—Hc3117
Ca5—Ca9—Ca14112.0 (15)Nc3—Cc4—Cc5114.3 (10)
Ca10—Ca9—Ca14121.9 (16)Nc3—Cc4—Oc4127.6 (13)
Ca9—Ca10—Ca11116.4 (15)Cc5—Cc4—Oc4118.1 (12)
Ca9—Ca10—Ha10124Cc4—Cc5—Cc6119.2 (10)
Ca11—Ca10—Ha10120Cc4—Cc5—Cc7113.8 (10)
Ca10—Ca11—Ca12123.6 (14)Cc4—Cc5—Cc9107.0 (9)
Ca10—Ca11—Ha11120Cc6—Cc5—Cc7103.4 (11)
Ca12—Ca11—Ha11117Cc6—Cc5—Cc9107.6 (10)
Ca11—Ca12—Ca13115.0 (13)Cc7—Cc5—Cc9104.9 (10)
Ca11—Ca12—Ha12124Nc1—Cc6—Cc5115.3 (10)
Ca13—Ca12—Ha12121Nc1—Cc6—Oc6120.6 (14)
Ca12—Ca13—Ca14122.2 (13)Cc5—Cc6—Oc6123.5 (16)
Ca12—Ca13—Ha13121Cc5—Cc7—Cc8116.2 (10)
Ca14—Ca13—Ha13117Cc5—Cc7—Hc7a108
Ca9—Ca14—Ca13118.1 (16)Cc5—Cc7—Hc7b107
Ca9—Ca14—Ha14119Cc8—Cc7—Hc7a108
Ca13—Ca14—Ha14122Cc8—Cc7—Hc7b109
Cb2—Nb1—Cb6127.7 (12)Hc7a—Cc7—Hc7b108
Cbi2—Nb1—Hb1116Cc7—Cc8—Hc8a108
Cbi6—Nb1—Hb1116Cc7—Cc8—Hc8b107
Nb1—Cb2—Nb3115.8 (13)Cc7—Cc8—Hc8c109
Nb1—Cb2—Ob2125.1 (14)Hc8a—Cc8—Hci8b111
Nb3—Ci2—Ob2113.6 (16)Hc8a—Cc8—Hci8c111
Cb2—Nb3—Cb4120.0 (14)Hc8b—Cc8—Hc8c111
Cb2—Nb3—Hb3120Cc5—Cc9—Cc10126.4 (16)
Cb4—Nb3—Hb3120Cc5—Cc9—Cc14115.5 (15)
Nb3—Cb4—Cb5119.9 (12)Cc10—Cc9—Cc14117.3 (15)
Nb3—Cb4—Ob4121.0 (15)Cc9—Cc10—Cc11121.8 (18)
Cb5—Cb4—Ob4116.4 (14)Cc9—Cc10—Hc10119
Cb4—Cb5—Cb6110.6 (9)Cc11—Cc10—Hc10118
Cb4—Cb5—Cb7107.2 (10)Cc10—Cc11—Cc12123.6 (15)
Cb4—Cb5—Cb9109.0 (10)Cc10—Cc11—Hc11118
Cb6—Cb5—Cb7108.8 (10)Cc12—Cc11—Hc11118
Cb6—Cb5—Cb9110.4 (9)Cc11—Cc12—Cc13111.6 (13)
Cb7—Cb5—Cb9110.9 (10)Cc11—Cc12—Hc12125
Nb1—Cb6—Cb5113.8 (13)Cc13—Cc12—Hc12123
Nb1—Cb6—Ob6125.5 (12)Cc12—Cc13—Cc14126.7 (19)
Cb5—Cb6—Ob6120.6 (10)Cc12—Cc13—Hc13117
Cb5—Cb7—Cb8110.9 (14)Cc14—Cc13—Hc13115
Cb5—Cb7—Hb7a107Cc9—Cc14—Cc13118.2 (17)
Cb5—Cb7—Hb7b107Cc9—Cc14—Hc14120
Cb8—Cb7—Hb7a107Cc13—Cc14—Hc14120
Cb8—Cb7—Hb7b110
Ca6—Na1—Ca2—Na38 (2)Cb9—Cb5—Cb6—Ob6−38 (2)
Ca6—Na1—Ca2—Oa2−172.1 (17)Cb4—Cb5—Cb7—Cb856.5 (16)
Ca2—Na1—Ca6—Ca5−14 (2)Cb6—Cb5—Cb7—Cb8−63.1 (16)
Ca2—Na1—Ca6—Oa6178.2 (16)Cb9—Cb5—Cb7—Cb8175.3 (13)
Na1—Ca2—Na3—Ca4−6 (3)Cb4—Cb5—Cb9—Cb10−15 (2)
Oa2—Ca2—Na3—Ca4174.5 (17)Cb4—Cb5—Cb9—Cb14166.7 (13)
Ca2—Na3—Ca4—Ca58 (3)Cb6—Cb5—Cb9—Cb10106 (2)
Ca2—Na3—Ca4—Oa4−175.5 (17)Cb6—Cb5—Cb9—Cb14−71.6 (16)
Na3—Ca4—Ca5—Ca6−10.4 (18)Cb7—Cb5—Cb9—Cb10−132.9 (18)
Na3—Ca4—Ca5—Ca7115.2 (16)Cb7—Cb5—Cb9—Cb1449.0 (16)
Na3—Ca4—Ca5—Ca9−125.4 (15)Cb5—Cb9—Cb10—Cb11178.8 (16)
Oa4—Ca4—Ca5—Ca6173.7 (16)Cb14—Cb9—Cb10—Cb11−3 (3)
Oa4—Ca4—Ca5—Ca7−60.7 (19)Cb5—Cb9—Cb14—Cb13169.4 (14)
Oa4—Ca4—Ca5—Ca958.8 (18)Cb10—Cb9—Cb14—Cb13−9 (3)
Ca4—Ca5—Ca6—Na113.8 (18)Cb9—Cb10—Cb11—Cb1214 (3)
Ca4—Ca5—Ca6—Oa6−178.3 (14)Cb10—Cb11—Cb12—Cb13−13 (2)
Ca7—Cai5—Ca6—Na1−103.5 (17)Cb11—Cb12—Cb13—Cb142 (3)
Ca7—Ca5—Ca6—Oa664.3 (17)Cb12—Cb13—Cb14—Cb910 (3)
Ca9—Ca5—Ca6—Na1−124.4 (15)Cc6—Nc1—Cc2—Nc31 (3)
Ca9—Ca5—Ca6—Oa6−67.8 (16)Cc6—Nc1—Cc2—Oc2170.4 (19)
Ca4—Ca5—Ca7—Ca862.7 (14)Cc2—Nc1—Cc6—Cc51 (3)
Ca6—Ca5—Ca7—Ca8−49.0 (15)Cc2—Nc1—Cc6—Oc6172 (2)
Ca9—Ca5—Ca7—Ca8176.5 (13)Nc1—Cc2—Nc3—Cc4−5 (3)
Ca4—Ca5—Ca9—Ca1081.9 (19)Oc2—Cc2—Nc3—Cc4−174 (2)
Ca4—Ca5—Ca9—Ca14−98.0 (15)Cc2—Nc3—Cc4—Cc57 (3)
Ca6—Ca5—Ca9—Ca10−161.0 (16)Cc2—Nc3—Cc4—Oc4−172 (2)
Ca6—Ca5—Ca9—Ca1419.1 (19)Nc3—Cc4—Cc5—Cc6−4 (1)
Ca7—Ca5—Ca9—Ca10−31 (2)Nc3—Cc4—Cc5—Cc7118.0 (16)
Ca7—Ca5—Ca9—Ca14149.4 (13)Nc3—Cc4—Cc5—Cc9−126.6 (15)
Ca5—Ca9—Ca10—Ca11175.8 (15)Oc4—Cc4—Cc5—Cc6175.0 (17)
Ca14—Ca9—Ca10—Ca11−4 (3)Oc4—Cc4—Cc5—Cc7−63 (2)
Ci5—Ci9—Ci14—Ca13−174.2 (14)Oc4—Cc4—Cc5—Cc953 (2)
Ca10—Ca9—Ca14—Ca136 (3)Cc4—Cc5—Cc6—Nc11 (2)
Ca9—Ca10—Ca11—Ca12−9 (3)Cc4—Cc5—Cc6—Oc6−169.9 (18)
Ca10—Ca11—Ca12—Ca1319 (2)Cc7—Cc5—Cc6—Nc1−121.0 (17)
Ca11—Ca12—Ca13—Ca14−17 (2)Cc7—Cc5—Cc6—Oc668 (2)
Ca12—Ca13—Ca14—Ca95 (3)Cc9—Cc5—Cc6—Nc1128.4 (16)
Cb6—Nb1—Cb2—Nb3−25 (3)Cc9—Cc5—Cc6—Oc6−42 (2)
Cb6—Nb1—Cb2—Ob2−177.7 (18)Cc4—Cc5—Cc7—Cc855.1 (18)
Cb2—Nb1—Cb6—Cb5−2 (3)Cc6—Cc5—Cc7—Cc8−75.7 (16)
Cb2—Nb1—Cb6—Ob6−177.9 (18)Cc9—Cc5—Cc7—Cc8171.7 (14)
Nb1—Cb2—Nb3—Cb422 (2)Cc4—Cc5—Cc9—Cc1062 (2)
Ob2—Cb2—Nb3—Cb4177.0 (15)Cc4—Cc5—Cc9—Cc14−107.2 (17)
Cb2—Nb3—Cb4—Cb57 (2)Cc6—Cc5—Cc9—Cc10−168.4 (18)
Cb2—Nb3—Cb4—Ob4167.6 (16)Cc6—Cc5—Cc9—Cc1422 (2)
Nb3—Cb4—Cb5—Cb6−32.1 (18)Cc7—Cc5—Cc9—Cc10−59 (2)
Nb3—Cb4—Cb5—Cb789.4 (16)Cc7—Cc5—Cc9—Cc14131.6 (16)
Nb3—Cb4—Cb5—Cb9−150.5 (14)Cc5—Cc9—Cc10—Cc11−168.8 (16)
Ob4—Cb4—Cb5—Cb6166.6 (15)Cc14—Cc9—Cc10—Cc111 (3)
Ob4—Cb4—Cb5—Cb7−71.9 (17)Cc5—Cc9—Cc14—Cc13177.0 (15)
Ob4—Cb4—Cb5—Cb948.2 (17)Cc10—Cc9—Cc14—Cc136 (3)
Cb4—Cb5—Cb6—Nb128.4 (18)Cc9—Cc10—Cc11—Cc12−6 (3)
Cb4—Cb5—Cb6—Ob6−155.2 (16)Cc10—Cc11—Cc12—Cc132 (3)
Cb7—Cb5—Cb6—Nb1−92.3 (16)Cc11—Cc12—Cc13—Cc145 (3)
Cb7—Cb5—Cb6—Ob684.1 (19)Cc12—Cc13—Cc14—Cc9−10 (3)
Cb9—Cb5—Cb6—Nb1145.8 (14)
Symmetry codes: (i) x, y, z−1; (ii) −x, −y, −z+1; (iii) −x, −y, −z; (iv) −x, −y+1, −z+1; (v) −x+1, −y+1, −z+1; (vi) −x, −y+1, −z+2; (vii) −x+1, −y, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
Na1—Ha1···Oa6iv1.031.979 (19)2.964 (19)159.2 (13)
Na3—Ha3···Oa4viii1.031.95 (2)2.98 (2)172.6 (15)
Nb1—Hb1···Ob6vii1.031.87 (2)2.87 (2)161.8 (14)
Nb3—Hb3···Ob4iii1.031.92 (2)2.92 (2)161.6 (16)
Nc1—Hc1···Oa6iv1.032.041 (19)3.049 (19)165.5 (13)
Nc3—Hc3···Oa4v1.032.10 (2)3.09 (2)160.3 (14)
Symmetry codes: (iii) −x, −y, −z; (iv) −x, −y+1, −z+1; (v) −x+1, −y+1, −z+1; (vii) −x+1, −y, −z+1; (viii) −x+1, −y+1, −z+2.

Experimental details

(Phenobarbital_Form_I)(Phenobarbital_Form_II)
Crystal data
Chemical formulaC12H12N2O3C12H12N2O3
Mr2786.832786.83
Crystal system, space groupMonoclinic, P21/NTriclinic, P1
Temperature (K)293293
a, b, c (Å)10.6907 (2), 47.1248 (11), 6.80017 (15)10.7313 (3), 23.5112 (7), 6.78309 (18)
α, β, γ (°)90, 94.1849 (8), 9090.9687 (9), 94.4757 (9), 88.1533 (12)
V (Å3)3416.76 (13)1705.13 (8)
Z126
Radiation typeCu Kα, λ = 1.540560 ÅCu Kα, λ = 1.540560 Å
Specimen shape, size (mm)?, ? × ? × ??, ? × ? × ?
Data collection
DiffractometerEnraf Nonius FR 590
diffractometer		Enraf Nonius FR 590
diffractometer
Specimen mounting??
Data collection mode??
Scan methodStationary detectorStationary detector
2θ values (°)2θfixed = ?2θfixed = ?
Refinement
R factors and goodness of fitRp = 3.067, Rwp = 4.000, Rexp = 1.818, RBragg = 2.822, χ2 = NOT FOUNDRp = 2.932, Rwp = 3.771, Rexp = 1.889, RBragg = 2.410, χ2 = NOT FOUND
No. of data points39463946
No. of parameters205204
No. of restraints117117

Computer programs: PEAKOC, FOX, FULLPROF, ORTEP-3, SHELX97 and PARST.

Selected geometric parameters (Å, º) for (Phenobarbital_Form_I) top
Na1—Ca61.366 (13)Cb6—Ob61.20 (2)
Na1—Ca21.381 (2)Cb9—Cb141.40 (2)
Ca2—Oa21.216 (13)Cb9—Cb101.41 (2)
Ca2—Na31.39 (2)Cb10—Cb111.39 (3)
Na3—Ca41.370 (13)Cb11—Cb121.40 (2)
Ca4—Oa41.21 (2)Cb12—Cb131.391 (18)
Ca4—Ca51.539 (18)Cb13—Cb141.40 (3)
Ca5—Ca61.527 (17)Cb7—Cb81.52 (2)
Ca5—Ca71.546 (17)Nc1—Cc61.37 (2)
Ca5—Ca91.55 (2)Nc1—Cc21.38 (3)
Ca6—Oa61.210 (18)Cc2—Oc21.222 (17)
Ca9—Ca101.40 (2)Cc2—Nc31.37 (2)
Ca9—Ca141.40 (3)Nc3—Cc41.366 (18)
Ca10—Ca111.39 (3)Cc4—Oc41.215 (17)
Ca11—Ca121.38 (3)Cc4—Cc51.531 (18)
Ca12—Ca131.39 (2)Cc5—Cc61.533 (18)
Ca13—Ca141.390 (3)Cc5—Cc91.54 (2)
Ca7—Ca81.51 (2)Cc5—Cc71.558 (16)
Nb1—Cb61.38 (2)Cc6—Oc61.22 (2)
Nb1—Cb21.38 (2)Cc9—Cc141.39 (2)
Cb2—Ob21.22 (2)Cc9—Cc101.39 (3)
Cb2—Nb31.384 (18)Cc10—Cc111.40 (3)
Nb3—Cb41.36 (2)Cc11—Cc121.394 (19)
Cb4—Ob41.213 (14)Cc12—Cc131.39 (2)
Cb4—Cb51.538 (18)Cc13—Cc141.38 (3)
Cb5—Cb61.540 (16)Cc7—Cc81.52 (2)
Cb5—Cb71.544 (16)
Oa6···Ca13i3.37 (2)Oc2···Na3vii3.34 (2)
Ob2···Cb10ii3.42 (2)Oc2···Oa2vii3.32 (3)
Ob2···Cb11iii3.31 (2)Oc4···Ca10viii3.34 (2)
Ob4···Ob4iv3.43 (2)Oc4···Ca7viii3.44 (2)
Ob6···Cb6v3.49 (2)Oc6···Ca12ix3.23 (2)
Ob6···Ob6v3.31 (2)Oc4···Cb13iv3.23 (2)
Nc1···Oa23.24 (2)Oc6···Cb11ii3.35 (2)
Nc1···Ca14vi3.35 (2)Oc6···Cb12ii3.29 (2)
Cc2···Oa23.39 (3)Cc12···Ob2vii3.36 (2)
Oc2···Ca2vii3.23 (3)Cc13···Ob6v3.50 (2)
Ca6—Na1—Ca2129.8 (10)Cb7—Cb5—Cb9110.2 (10)
Oa2—Ca2—Na1124.1 (10)Ob6—Cb6—Nb1122.3 (15)
Oa2—Ca2—Na3120.0 (9)Ob6—Cb6—Cb5117.4 (13)
Na1—Ca2—Na3115.0 (15)Nb1—Cb6—Cb5114.8 (11)
Ca4—Na3—Ca2125.8 (9)Cb14—Cb9—Cb10116.7 (13)
Oa4—Ca4—Na3116.6 (12)Cb14—Cb9—Cb5116.8 (14)
Oa4—Ca4—Ca5125.9 (15)Cb10—Cb9—Cb5126.4 (13)
Na3—Ca4—Ca5117.5 (8)Cb11—Cb10—Cb9121.6 (15)
Ca6—Ca5—Ca4116.2 (10)Cb10—Cb11—Cb12119.9 (16)
Ca6—Ca5—Ca7110.3 (8)Cb13—Cb12—Cb11118.5 (12)
Ca4—Ca5—Ca7105.4 (9)Cb12—Cb13—Cb14119.6 (14)
Ca6—Ca5—Ca9107.6 (9)Cb13—Cb14—Cb9121.0 (16)
Ca4—Ca5—Ca9109.5 (9)Cb8—Cb7—Cb5107.4 (11)
Ca7—Ca5—Ca9107.6 (10)Cc6—Nc1—Cc2119.4 (13)
Oa6—Ca6—Na1125.9 (11)Oc2—Cc2—Nc3119.6 (12)
Oa6—Ca6—Ca5118.2 (12)Oc2—Cc2—Nc1120.1 (13)
Na1—Ca6—Ca5114.8 (8)Nc3—Cc2—Nc1119.9 (13)
Ca10—Ca9—Ca14117.2 (15)Cc4—Nc3—Cc2128.5 (12)
Ca10—Ca9—Ca5124.5 (14)Oc4—Cc4—Nc3121.3 (12)
Ca14—Ca9—Ca5118.2 (15)Oc4—Cc4—Cc5124.4 (11)
Ca11—Ca10—Ca9127.6 (15)Nc3—Cc4—Cc5114.3 (10)
Ca12—Ca11—Ca10112.3 (19)Cc4—Cc5—Cc6114.3 (9)
Ca11—Ca12—Ca13122.9 (15)Cc4—Cc5—Cc9105.4 (9)
Ca14—Ca13—Ca12122.8 (14)Cc6—Cc5—Cc9110.7 (10)
Ca13—Ca14—Ca9116.7 (16)Cc4—Cc5—Cc7108.2 (10)
Ca8—Ca7—Ca5110.7 (11)Cc6—Cc5—Cc7109.1 (10)
Cb6—Nb1—Cb2127.9 (14)Cc9—Cc5—Cc7108.8 (10)
Ob2—Cb2—Nb1118.4 (16)Oc6—Cc6—Nc1117.2 (15)
Ob2—Cb2—Nb3128.3 (14)Oc6—Cc6—Cc5119.9 (14)
Nb1—Cb2—Nb3111.4 (12)Nc1—Cc6—Cc5121.5 (11)
Cb4—Nb3—Cb2131.2 (12)Cc14—Cc9—Cc10112.2 (15)
Ob4—Cb4—Nb3121.7 (12)Cc14—Cc9—Cc5123.2 (15)
Ob4—Cb4—Cb5124.2 (10)Cc10—Cc9—Cc5123.5 (16)
Nb3—Cb4—Cb5113.9 (13)Cc9—Cc10—Cc11128.9 (18)
Cb4—Cb5—Cb6112.4 (8)Cc12—Cc11—Cc10114.0 (15)
Cb4—Cb5—Cb7111.1 (10)Cc13—Cc12—Cc11120.0 (12)
Cb6—Cb5—Cb7108.1 (9)Cc14—Cc13—Cc12120.2 (17)
Cb4—Cb5—Cb9103.3 (9)Cc13—Cc14—Cc9121.1 (16)
Cb6—Cb5—Cb9111.7 (10)Cc8—Cc7—Cc5118.9 (11)
Ca6—Na1—Ca2—Oa2−175.8 (18)Cb9—Cb5—Cb6—Nb183.4 (14)
Ca6—Na1—Ca2—Na3−7 (3)Cb4—Cb5—Cb9—Cb14−75.1 (17)
Oa2—Ca2—Na3—Ca4179.6 (17)Cb6—Cb5—Cb9—Cb14163.9 (14)
Na1—Ca2—Na3—Ca410 (3)Cb7—Cb5—Cb9—Cb1443.6 (18)
Ca2—Na3—Ca4—Oa4172.5 (17)Cb4—Cb5—Cb9—Cb10109.4 (18)
Ca2—Na3—Ca4—Ca5−10 (2)Cb6—Cb5—Cb9—Cb10−12 (2)
Oa4—Ca4—Ca5—Ca6−177.0 (17)Cb7—Cb5—Cb9—Cb10−131.9 (17)
Na3—Ca4—Ca5—Ca65.5 (19)Cb14—Cb9—Cb10—Cb117 (3)
Oa4—Ca4—Ca5—Ca7−55 (2)Cb5—Cb9—Cb10—Cb11−177.5 (15)
Na3—Ca4—Ca5—Ca7127.9 (14)Cb9—Cb10—Cb11—Cb12−7 (3)
Oa4—Ca4—Ca5—Ca961 (2)Cb10—Cb11—Cb12—Cb1312 (2)
Na3—Ca4—Ca5—Ca9−116.6 (15)Cb11—Cb12—Cb13—Cb14−17 (2)
Ca2—Na1—Ca6—Oa6−164.5 (15)Cb12—Cb13—Cb14—Cb917 (3)
Ca2—Na1—Ca6—Ca53 (3)Cb10—Cb9—Cb14—Cb13−12 (3)
Ca4—Ca5—Ca6—Oa6166.4 (15)Cb5—Cb9—Cb14—Cb13172.1 (14)
Ca7—Ca5—Ca6—Oa646.6 (19)Cb4—Cb5—Cb7—Cb8−67.7 (14)
Ca9—Ca5—Ca6—Oa6−70.5 (18)Cb6—Cb5—Cb7—Cb856.1 (14)
Ca4—Ca5—Ca6—Na1−2.5 (18)Cb9—Cb5—Cb7—Cb8178.4 (12)
Ca7—Ca5—Ca6—Na1−122.2 (14)Cc6—Nc1—Cc2—Oc2169.6 (18)
Ca9—Ca5—Ca6—Na1120.6 (15)Cc6—Nc1—Cc2—Nc3−2 (3)
Ca6—Ca5—Ca9—Ca1079.3 (19)Oc2—Cc2—Nc3—Cc4−177.3 (18)
Ca4—Ca5—Ca9—Ca10−153.6 (16)Nc1—Cc2—Nc3—Cc4−6 (3)
Ca7—Ca5—Ca9—Ca10−40 (2)Cc2—Nc3—Cc4—Oc4177.8 (19)
Ca6—Ca5—Ca9—Ca14−97.1 (16)Cc2—Nc3—Cc4—Cc51 (3)
Ca4—Ca5—Ca9—Ca1430.1 (19)Oc4—Cc4—Cc5—Cc6−166.9 (17)
Ca7—Ca5—Ca9—Ca14144.1 (15)Nc3—Cc4—Cc5—Cc69.9 (19)
Ca14—Ca9—Ca10—Ca11−8 (3)Oc4—Cc4—Cc5—Cc971 (2)
Ca5—Ca9—Ca10—Ca11175.7 (16)Nc3—Cc4—Cc5—Cc9−111.9 (15)
Ca9—Ca10—Ca11—Ca128 (3)Oc4—Cc4—Cc5—Cc7−45 (2)
Ca10—Ca11—Ca12—Ca13−4 (3)Nc3—Cc4—Cc5—Cc7131.8 (14)
Ca11—Ca12—Ca13—Ca140 (3)Cc2—Nc1—Cc6—Oc6179.8 (18)
Ca12—Ca13—Ca14—Ca90 (3)Cc2—Nc1—Cc6—Cc514 (3)
Ca10—Ca9—Ca14—Ca133 (3)Cc4—Cc5—Cc6—Oc6176.7 (16)
Ca5—Ca9—Ca14—Ca13179.9 (14)Cc9—Cc5—Cc6—Oc6−64 (2)
Ca6—Ca5—Ca7—Ca863.0 (15)Cc7—Cc5—Cc6—Oc655 (2)
Ca4—Ca5—Ca7—Ca8−63.2 (15)Cc4—Cc5—Cc6—Nc1−18 (2)
Ca9—Ca5—Ca7—Ca8−179.9 (13)Cc9—Cc5—Cc6—Nc1101.3 (17)
Cb6—Nb1—Cb2—Ob2169.3 (16)Cc7—Cc5—Cc6—Nc1−138.9 (16)
Cb6—Nb1—Cb2—Nb34 (2)Cc4—Cc5—Cc9—Cc14102.5 (18)
Ob2—Cb2—Nb3—Cb4−177.4 (18)Cc6—Cc5—Cc9—Cc14−22 (2)
Nb1—Cb2—Nb3—Cb4−14 (3)Cc7—Cc5—Cc9—Cc14−141.6 (16)
Cb2—Nb3—Cb4—Ob4173.8 (17)Cc4—Cc5—Cc9—Cc10−64.6 (19)
Cb2—Nb3—Cb4—Cb5−2 (3)Cc6—Cc5—Cc9—Cc10171.3 (16)
Ob4—Cb4—Cb5—Cb6−151.0 (16)Cc7—Cc5—Cc9—Cc1051 (2)
Nb3—Cb4—Cb5—Cb624.5 (17)Cc14—Cc9—Cc10—Cc117 (3)
Ob4—Cb4—Cb5—Cb7−30 (2)Cc5—Cc9—Cc10—Cc11175.3 (16)
Nb3—Cb4—Cb5—Cb7145.8 (13)Cc9—Cc10—Cc11—Cc12−1 (3)
Ob4—Cb4—Cb5—Cb988.4 (19)Cc10—Cc11—Cc12—Cc135 (2)
Nb3—Cb4—Cb5—Cb9−96.1 (15)Cc11—Cc12—Cc13—Cc14−17 (3)
Cb2—Nb1—Cb6—Ob6172.3 (16)Cc12—Cc13—Cc14—Cc924 (3)
Cb2—Nb1—Cb6—Cb519 (2)Cc10—Cc9—Cc14—Cc13−18 (3)
Cb4—Cb5—Cb6—Ob6173.2 (14)Cc5—Cc9—Cc14—Cc13173.5 (15)
Cb7—Cb5—Cb6—Ob650.3 (16)Cc4—Cc5—Cc7—Cc8−63.2 (16)
Cb9—Cb5—Cb6—Ob6−71.2 (16)Cc6—Cc5—Cc7—Cc861.7 (17)
Cb4—Cb5—Cb6—Nb1−32.3 (16)Cc9—Cc5—Cc7—Cc8−177.3 (14)
Cb7—Cb5—Cb6—Nb1−155.2 (12)
Symmetry codes: (i) x, y, z+1; (ii) −x, −y, −z+1; (iii) −x+1, −y+1, −z; (iv) −x+1, −y, −z+1; (v) −x, −y, −z; (vi) x−1/2, −y+1/2, z−1/2; (vii) x, y, z−1; (viii) x+1/2, −y+1/2, z−1/2; (ix) x−1/2, −y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) for (Phenobarbital_Form_I) top
D—H···AD—HH···AD···AD—H···A
Na1—Ha1···Oa4vi1.031.917 (20)2.931 (20)167.5 (14)
Na3—Ha3···Oa6x1.032.016 (21)2.965 (20)151.6 (13)
Nb1—Hb1···Ob6v1.031.958 (19)2.906 (19)151.6 (14)
Nb3—Hb3···Ob4iv1.031.887 (19)2.887 (19)162.9 (14)
Nc1—Hc1···Oa4xi1.032.055 (22)2.995 (21)150.4 (14)
Nc3—Hc3···Oa6xii1.031.989 (19)3.006 (19)168.9 (13)
Symmetry codes: (iv) −x+1, −y, −z+1; (v) −x, −y, −z; (vi) x−1/2, −y+1/2, z−1/2; (x) x+1/2, −y+1/2, z+1/2; (xi) −x−1/2, y+1/2, −z−1/2; (xii) −x+1/2, y+1/2, −z+3/2.
Selected geometric parameters (Å, º) for (Phenobarbital_Form_II) top
Na1—Ca21.36 (2)Cb5—Cb91.55 (2)
Na1—Ca61.364 (14)Cb6—Ob61.230 (15)
Ca2—Na31.370 (19)Cb7—Cb81.54 (2)
Ca2—Oa21.217 (13)Cb9—Cb101.39 (2)
Na3—Ca41.357 (14)Cb9—Cb41.40 (2)
Ca4—Cai51.516 (16)Cb10—Cb111.40 (3)
Ca4—Oa41.211 (19)Cb11—Cb121.39 (2)
Ca5—Ca61.519 (15)Cb12—Cb131.39 (2)
Ca5—Ca71.554 (18)Cb13—Cb141.39 (3)
Ca5—Ca91.54 (2)Nc1—Cc21.39 (3)
Ca6—Oa61.234 (19)Nc1—Cc61.381 (17)
Ca7—Ca81.51 (2)Cc2—Nc31.38 (2)
Ca9—Ca101.39 (2)Cc2—Oc21.217 (19)
Ca9—Ca141.39 (3)Nc3—Cc41.375 (17)
Ca10—Ca111.39 (2)Cc4—Cc51.53 (2)
Ca11—Ca121.39 (2)Cc4—Oc41.22 (2)
Ca12—Ca131.393 (19)Cc5—Cc61.54 (2)
Ca13—Ca141.39 (2)Cc5—Cc71.554 (15)
Nb1—Cb21.372 (17)Cc5—Cc91.55 (2)
Nb1—Cb61.36 (2)Cc6—Oc61.22 (3)
Cb2—Nb31.38 (2)Cc7—Cc81.53 (2)
Cbi2—Ob21.22 (2)Cc9—Cc101.39 (3)
Nbi3—Cb41.37 (2)Cc9—Cc141.39 (2)
Cb4—Cb51.533 (17)Cc10—Cc111.38 (3)
Cb4—Ob41.22 (2)Cc11—Cc121.41 (2)
Cb5—Cb61.529 (18)Cc12—Cc131.40 (3)
Cb5—Cb71.542 (17)Cc13—Cc141.40 (3)
Oa6···Ca13i3.48 (2)Oc2···Oa2i3.17 (2)
Ob2···Cb10ii3.41 (2)Oc2···Oa6iv3.43 (2)
Ob2···Cb11ii3.39 (2)Oc4···Ca10v3.25 (2)
Ob4···Ob4iii3.38 (2)Oc6···Ca12vi3.22 (2)
Nc1···Oa23.16 (2)Cc8···Oa23.49 (2)
Cc2···Oa23.40 (3)Cc14···Ca12iv3.47 (2)
Cc2···Oa2i3.47 (3)Oc4···Cb13vii3.20 (2)
Nc3···Oa2i3.40 (3)Oc6···Cb11ii3.14 (2)
Oc2···Na13.32 (2)Oc6···Cb12ii3.35 (2)
Oc2···Ca2i3.31 (3)Cc12···Ob2i3.34 (3)
Oc2···Na3i3.44 (2)
Ca2—Na1—Ca6123.8 (10)Cb7—Cb5—Cb9110.9 (10)
Na1—Ca2—Na3112.3 (14)Nb1—Cb6—Cb5113.8 (13)
Na1—Ca2—Oa2124.7 (10)Nb1—Cb6—Ob6125.5 (12)
Na3—Ca2—Oa2123.0 (10)Cb5—Cb6—Ob6120.6 (10)
Ca2—Na3—Ca4129.4 (10)Cb5—Cb7—Cb8110.9 (14)
Na3—Ca4—Ca5121.5 (9)Cb5—Cb9—Cb10131.7 (13)
Na3—Ca4—Oa4116.6 (12)Cb5—Cb9—Cb14110.9 (14)
Ca5—Ca4—Oa4121.9 (13)Cb10—Cb9—Cb14117.4 (13)
Ca4—Ca5—Ca6105.1 (9)Cb9—Cb10—Cb11123.1 (14)
Ca4—Ca5—Ca7103.4 (9)Cb10—Cb11—Cb12117.2 (16)
Ca4—Ca5—Ca9105.5 (9)Cb11—Cb12—Cb13119.1 (11)
Ca6—Ca5—Ca7109.6 (9)Cb2—Cb13—Cb14121.7 (14)
Ca6—Ca5—Ca9118.1 (10)Cb9—Cb14—Cb13119.3 (16)
Ca7—Ca5—Ca9113.5 (10)Cc2—Nc1—Cc6124.7 (12)
Na1—Ca6—Ca5126.1 (9)Nc1—Cc2—Nc3119.6 (15)
Na1—Ca6—Oa6118.1 (12)Nc1—Cc2—Oc2115.9 (13)
Ca5—Ca6—Oa6114.7 (13)Nc3—Cc2—Oc2123.5 (14)
Ca5—Ca7—Ca8113.9 (11)Cc2—Nc3—Cc4126.5 (12)
Ca5—Ca9—Ca10126.1 (15)Nc3—Cc4—Cc5114.3 (10)
Ca5—Ca9—Ca14112.0 (15)Nc3—Cc4—Oc4127.6 (13)
Ca10—Ca9—Ca14121.9 (16)Cc5—Cc4—Oc4118.1 (12)
Ca9—Ca10—Ca11116.4 (15)Cc4—Cc5—Cc6119.2 (10)
Ca10—Ca11—Ca12123.6 (14)Cc4—Cc5—Cc7113.8 (10)
Ca11—Ca12—Ca13115.0 (13)Cc4—Cc5—Cc9107.0 (9)
Ca12—Ca13—Ca14122.2 (13)Cc6—Cc5—Cc7103.4 (11)
Ca9—Ca14—Ca13118.1 (16)Cc6—Cc5—Cc9107.6 (10)
Cb2—Nb1—Cb6127.7 (12)Cc7—Cc5—Cc9104.9 (10)
Nb1—Cb2—Nb3115.8 (13)Nc1—Cc6—Cc5115.3 (10)
Nb1—Cb2—Ob2125.1 (14)Nc1—Cc6—Oc6120.6 (14)
Nb3—Ci2—Ob2113.6 (16)Cc5—Cc6—Oc6123.5 (16)
Cb2—Nb3—Cb4120.0 (14)Cc5—Cc7—Cc8116.2 (10)
Nb3—Cb4—Cb5119.9 (12)Cc5—Cc9—Cc10126.4 (16)
Nb3—Cb4—Ob4121.0 (15)Cc5—Cc9—Cc14115.5 (15)
Cb5—Cb4—Ob4116.4 (14)Cc10—Cc9—Cc14117.3 (15)
Cb4—Cb5—Cb6110.6 (9)Cc9—Cc10—Cc11121.8 (18)
Cb4—Cb5—Cb7107.2 (10)Cc10—Cc11—Cc12123.6 (15)
Cb4—Cb5—Cb9109.0 (10)Cc11—Cc12—Cc13111.6 (13)
Cb6—Cb5—Cb7108.8 (10)Cc12—Cc13—Cc14126.7 (19)
Cb6—Cb5—Cb9110.4 (9)Cc9—Cc14—Cc13118.2 (17)
Ca6—Na1—Ca2—Na38 (2)Cb9—Cb5—Cb6—Ob6−38 (2)
Ca6—Na1—Ca2—Oa2−172.1 (17)Cb4—Cb5—Cb7—Cb856.5 (16)
Ca2—Na1—Ca6—Ca5−14 (2)Cb6—Cb5—Cb7—Cb8−63.1 (16)
Ca2—Na1—Ca6—Oa6178.2 (16)Cb9—Cb5—Cb7—Cb8175.3 (13)
Na1—Ca2—Na3—Ca4−6 (3)Cb4—Cb5—Cb9—Cb10−15 (2)
Oa2—Ca2—Na3—Ca4174.5 (17)Cb4—Cb5—Cb9—Cb14166.7 (13)
Ca2—Na3—Ca4—Ca58 (3)Cb6—Cb5—Cb9—Cb10106 (2)
Ca2—Na3—Ca4—Oa4−175.5 (17)Cb6—Cb5—Cb9—Cb14−71.6 (16)
Na3—Ca4—Ca5—Ca6−10.4 (18)Cb7—Cb5—Cb9—Cb10−132.9 (18)
Na3—Ca4—Ca5—Ca7115.2 (16)Cb7—Cb5—Cb9—Cb1449.0 (16)
Na3—Ca4—Ca5—Ca9−125.4 (15)Cb5—Cb9—Cb10—Cb11178.8 (16)
Oa4—Ca4—Ca5—Ca6173.7 (16)Cb14—Cb9—Cb10—Cb11−3 (3)
Oa4—Ca4—Ca5—Ca7−60.7 (19)Cb5—Cb9—Cb14—Cb13169.4 (14)
Oa4—Ca4—Ca5—Ca958.8 (18)Cb10—Cb9—Cb14—Cb13−9 (3)
Ca4—Ca5—Ca6—Na113.8 (18)Cb9—Cb10—Cb11—Cb1214 (3)
Ca4—Ca5—Ca6—Oa6−178.3 (14)Cb10—Cb11—Cb12—Cb13−13 (2)
Ca7—Cai5—Ca6—Na1−103.5 (17)Cb11—Cb12—Cb13—Cb142 (3)
Ca7—Ca5—Ca6—Oa664.3 (17)Cb12—Cb13—Cb14—Cb910 (3)
Ca9—Ca5—Ca6—Na1−124.4 (15)Cc6—Nc1—Cc2—Nc31 (3)
Ca9—Ca5—Ca6—Oa6−67.8 (16)Cc6—Nc1—Cc2—Oc2170.4 (19)
Ca4—Ca5—Ca7—Ca862.7 (14)Cc2—Nc1—Cc6—Cc51 (3)
Ca6—Ca5—Ca7—Ca8−49.0 (15)Cc2—Nc1—Cc6—Oc6172 (2)
Ca9—Ca5—Ca7—Ca8176.5 (13)Nc1—Cc2—Nc3—Cc4−5 (3)
Ca4—Ca5—Ca9—Ca1081.9 (19)Oc2—Cc2—Nc3—Cc4−174 (2)
Ca4—Ca5—Ca9—Ca14−98.0 (15)Cc2—Nc3—Cc4—Cc57 (3)
Ca6—Ca5—Ca9—Ca10−161.0 (16)Cc2—Nc3—Cc4—Oc4−172 (2)
Ca6—Ca5—Ca9—Ca1419.1 (19)Nc3—Cc4—Cc5—Cc6−4 (1)
Ca7—Ca5—Ca9—Ca10−31 (2)Nc3—Cc4—Cc5—Cc7118.0 (16)
Ca7—Ca5—Ca9—Ca14149.4 (13)Nc3—Cc4—Cc5—Cc9−126.6 (15)
Ca5—Ca9—Ca10—Ca11175.8 (15)Oc4—Cc4—Cc5—Cc6175.0 (17)
Ca14—Ca9—Ca10—Ca11−4 (3)Oc4—Cc4—Cc5—Cc7−63 (2)
Ci5—Ci9—Ci14—Ca13−174.2 (14)Oc4—Cc4—Cc5—Cc953 (2)
Ca10—Ca9—Ca14—Ca136 (3)Cc4—Cc5—Cc6—Nc11 (2)
Ca9—Ca10—Ca11—Ca12−9 (3)Cc4—Cc5—Cc6—Oc6−169.9 (18)
Ca10—Ca11—Ca12—Ca1319 (2)Cc7—Cc5—Cc6—Nc1−121.0 (17)
Ca11—Ca12—Ca13—Ca14−17 (2)Cc7—Cc5—Cc6—Oc668 (2)
Ca12—Ca13—Ca14—Ca95 (3)Cc9—Cc5—Cc6—Nc1128.4 (16)
Cb6—Nb1—Cb2—Nb3−25 (3)Cc9—Cc5—Cc6—Oc6−42 (2)
Cb6—Nb1—Cb2—Ob2−177.7 (18)Cc4—Cc5—Cc7—Cc855.1 (18)
Cb2—Nb1—Cb6—Cb5−2 (3)Cc6—Cc5—Cc7—Cc8−75.7 (16)
Cb2—Nb1—Cb6—Ob6−177.9 (18)Cc9—Cc5—Cc7—Cc8171.7 (14)
Nb1—Cb2—Nb3—Cb422 (2)Cc4—Cc5—Cc9—Cc1062 (2)
Ob2—Cb2—Nb3—Cb4177.0 (15)Cc4—Cc5—Cc9—Cc14−107.2 (17)
Cb2—Nb3—Cb4—Cb57 (2)Cc6—Cc5—Cc9—Cc10−168.4 (18)
Cb2—Nb3—Cb4—Ob4167.6 (16)Cc6—Cc5—Cc9—Cc1422 (2)
Nb3—Cb4—Cb5—Cb6−32.1 (18)Cc7—Cc5—Cc9—Cc10−59 (2)
Nb3—Cb4—Cb5—Cb789.4 (16)Cc7—Cc5—Cc9—Cc14131.6 (16)
Nb3—Cb4—Cb5—Cb9−150.5 (14)Cc5—Cc9—Cc10—Cc11−168.8 (16)
Ob4—Cb4—Cb5—Cb6166.6 (15)Cc14—Cc9—Cc10—Cc111 (3)
Ob4—Cb4—Cb5—Cb7−71.9 (17)Cc5—Cc9—Cc14—Cc13177.0 (15)
Ob4—Cb4—Cb5—Cb948.2 (17)Cc10—Cc9—Cc14—Cc136 (3)
Cb4—Cb5—Cb6—Nb128.4 (18)Cc9—Cc10—Cc11—Cc12−6 (3)
Cb4—Cb5—Cb6—Ob6−155.2 (16)Cc10—Cc11—Cc12—Cc132 (3)
Cb7—Cb5—Cb6—Nb1−92.3 (16)Cc11—Cc12—Cc13—Cc145 (3)
Cb7—Cb5—Cb6—Ob684.1 (19)Cc12—Cc13—Cc14—Cc9−10 (3)
Cb9—Cb5—Cb6—Nb1145.8 (14)
Symmetry codes: (i) x, y, z−1; (ii) −x, −y, −z+1; (iii) −x, −y, −z; (iv) −x, −y+1, −z+1; (v) −x+1, −y+1, −z+1; (vi) −x, −y+1, −z+2; (vii) −x+1, −y, −z+1.
Hydrogen-bond geometry (Å, º) for (Phenobarbital_Form_II) top
D—H···AD—HH···AD···AD—H···A
Na1—Ha1···Oa6iv1.031.979 (19)2.964 (19)159.2 (13)
Na3—Ha3···Oa4viii1.031.951 (20)2.975 (20)172.6 (15)
Nb1—Hb1···Ob6vii1.031.874 (21)2.871 (20)161.8 (14)
Nb3—Hb3···Ob4iii1.031.921 (20)2.916 (20)161.6 (16)
Nc1—Hc1···Oa6iv1.032.041 (19)3.049 (19)165.5 (13)
Nc3—Hc3···Oa4v1.032.103 (21)3.092 (21)160.3 (14)
Symmetry codes: (iii) −x, −y, −z; (iv) −x, −y+1, −z+1; (v) −x+1, −y+1, −z+1; (vii) −x+1, −y, −z+1; (viii) −x+1, −y+1, −z+2.
 

Subscribe to Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials

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