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The crystal structure of a new cocrystal of carbamazepine (systematic name: 5H-dibenzo[b,f]azepine-5-carboxamide, C15H12N2O) and DL-tartaric acid (C4H6O6), obtained by liquid-assisted grinding, was solved by powder X-ray diffraction (PXRD). The high-resolution PXRD pattern of this new phase was recorded at room temperature thanks to synchrotron experiments at the European Synchrotron Radiation Facility (Grenoble, France). The starting structural model was generated by a Monte-Carlo simulated annealing method. The final structure was obtained through Rietveld refinement and an energy minimization simulation was used to estimate the H-atom positions. The stability of the proposed structure as a function of temperature was also assessed from mol­ecular dynamics simulations. The symmetry is monoclinic (space group P21/c) and contains eight mol­ecules per unit cell, namely, four DL-tartaric acid and four carbamazepine mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229620000868/yo3068sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620000868/yo3068Isup2.hkl
Contains datablock I

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S2053229620000868/yo3068Isup3.rtv
Contains datablock I

CCDC reference: 1979490

Computing details top

Data collection: WinPlotr (Roisnel & Rodriguez-Carvajal, 2002); cell refinement: DICVOL (Boultif & Louër, 2004); program(s) used to solve structure: DASH (David et al., 2006); program(s) used to refine structure: MAUD (Luterotti, 2010) and JANA2006 (Petříček et al., 2014); molecular graphics: Mercury (Macrae et al., 2020).

5H-Dibenzo[b,f]azepine-5-carboxamide–DL-tartaric acid (1/1) top
Crystal data top
C15H12N2O·C4H6O6β = 92.959 (2)°
Mr = 386.4V = 1761.03 (10) Å3
Monoclinic, P21/cZ = 4
Hall symbol: -P 2ycbF(000) = 808
a = 4.96273 (12) ÅDx = 1.457 Mg m3
b = 9.3760 (3) ÅSynchrotron radiation
c = 37.8971 (13) ÅT = 293 K
Data collection top
Synchrotron
diffractometer
2θmin = 0.501°, 2θmax = 14.998°
Refinement top
Rp = 0.12177 restraints
Rwp = 0.17387 constraints
Rexp = 0.073H atoms treated by a mixture of independent and constrained refinement
R(F) = 0.175Weighting scheme based on measured s.u.'s
9666 data points(Δ/σ)max = 0.035
Excluded region(s): from 1.68 to 1.710, from 2.27 to 2.300, from 2.58 to 2.590, from 5.05 to 5.070, from 5.58 to 5.590, from 8.36 to 8.380, from 8.99 to 9.000, from 9.37 to 9.380Background function: Manual background
Profile function: Pseudo-VoigtPreferred orientation correction: none
106 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1b0.143 (2)0.9642 (10)0.38043 (18)0.0314 (16)*
N1b0.3043 (11)0.7706 (8)0.34986 (9)0.0314 (16)*
N2b0.0655 (19)0.7444 (12)0.40339 (14)0.0314 (16)*
H1b0.13200.64240.40420.0314 (16)*
H2b0.03750.78700.42490.0314 (16)*
C1b0.663 (2)1.0317 (10)0.2906 (3)0.0314 (16)*
H3b0.8037291.0968520.2914360.0314 (16)*
C2b0.5924 (16)0.9497 (9)0.3199 (2)0.0314 (16)*
H4b0.6859710.9598940.3403440.0314 (16)*
C3b0.3835 (14)0.8524 (8)0.31894 (13)0.0314 (16)*
C4b0.3377 (13)0.6191 (8)0.34740 (11)0.0314 (16)*
C5b0.1763 (16)0.5405 (7)0.32527 (16)0.0314 (16)*
C6b0.209 (2)0.3926 (7)0.3251 (2)0.0314 (16)*
H5b0.10420.3374580.3107010.0314 (16)*
C7b0.391 (3)0.3260 (9)0.3458 (3)0.0314 (16)*
H6b0.4086160.2272350.3451890.0314 (16)*
C8b0.525 (3)1.0171 (10)0.2602 (3)0.0314 (16)*
H7b0.5725641.0723330.2404750.0314 (16)*
C9b0.318 (3)0.9207 (10)0.25918 (18)0.0314 (16)*
H8b0.2260430.9115160.2385290.0314 (16)*
C10b0.2409 (18)0.8357 (8)0.28832 (13)0.0314 (16)*
C11b0.1717 (14)0.8339 (10)0.37852 (13)0.0314 (16)*
C12b0.5215 (16)0.5517 (11)0.36822 (17)0.0314 (16)*
H9b0.6274020.6054530.3827860.0314 (16)*
C13b0.548 (2)0.4052 (12)0.3674 (2)0.0314 (16)*
H10b0.6707580.3601920.3813210.0314 (16)*
C14b0.0098 (16)0.6071 (9)0.30167 (17)0.0314 (16)*
H11b0.1659850.5564590.2973980.0314 (16)*
C15b0.0209 (17)0.7332 (9)0.28555 (14)0.0314 (16)*
H12b0.1145420.7590780.2707220.0314 (16)*
C1a0.3917 (16)0.4532 (9)0.93122 (15)0.0314 (16)*
O1a0.379 (3)0.5801 (9)0.9456 (3)0.0314 (16)*
H1a0.09670.47990.90080.0314 (16)*
O2a0.248 (2)0.4111 (14)0.9064 (3)0.0314 (16)*
C2a0.6180 (14)0.3639 (8)0.94855 (18)0.0314 (16)*
H2a0.7299270.3322570.9312320.0314 (16)*
O3a0.785 (2)0.4441 (10)0.9722 (4)0.0314 (16)*
H3a0.68390.53410.97540.0314 (16)*
C3a0.4937 (15)0.2330 (6)0.9665 (2)0.0314 (16)*
H4a0.3620390.1945860.9509470.0314 (16)*
O4a0.374 (2)0.2691 (11)0.9979 (3)0.0314 (16)*
H5a0.52210.29851.01680.0314 (16)*
C4a0.7217 (19)0.1295 (8)0.9760 (2)0.0314 (16)*
O5a0.849 (3)0.0676 (14)0.9540 (3)0.0314 (16)*
O6a0.760 (2)0.1141 (14)1.0102 (3)0.0314 (16)*
H6a0.91850.05731.0170.0314 (16)*
Geometric parameters (Å, º) top
O1b—C11b1.232 (13)C8b—C9b1.372 (16)
N1b—C3b1.438 (8)C9b—H8b0.93
N1b—C4b1.433 (11)C9b—C10b1.399 (10)
N1b—C11b1.375 (8)C10b—C15b1.463 (12)
N2b—H1b0.86C12b—H9b0.93
N2b—H2b0.86C12b—C13b1.380 (8)
N2b—C11b1.349 (11)C13b—H10b0.93
C1b—H3b0.93C14b—H11b0.93
C1b—C2b1.379 (10)C14b—C15b1.337 (11)
C1b—C8b1.376 (11)C15b—H12b0.93
C2b—H4b0.93C1a—O1a1.312 (9)
C2b—C3b1.383 (11)C1a—O2a1.215 (13)
C3b—C10b1.399 (9)C1a—C2a1.523 (10)
C4b—C5b1.399 (9)C2a—H2a0.93
C4b—C12b1.389 (10)C2a—O3a1.408 (13)
C5b—C6b1.396 (10)C2a—C3a1.546 (10)
C5b—C14b1.459 (10)C3a—H4a0.93
C6b—H5b0.93C3a—O4a1.401 (14)
C6b—C7b1.378 (9)C3a—C4a1.520 (11)
C7b—H6b0.93C4a—O5a1.219 (16)
C7b—C13b1.373 (8)C4a—O6a1.308 (13)
C8b—H7b0.93
C3b—N1b—C4b116.7 (5)C9b—C10b—C15b119.5 (7)
C3b—N1b—C11b120.9 (7)O1b—C11b—N1b121.6 (7)
C4b—N1b—C11b121.9 (6)O1b—C11b—N2b122.4 (7)
H1b—N2b—H2b120N1b—C11b—N2b115.9 (8)
H1b—N2b—C11b120C4b—C12b—H9b119.9
H2b—N2b—C11b120C4b—C12b—C13b120.2 (8)
H3b—C1b—C2b119.97H9b—C12b—C13b119.89
H3b—C1b—C8b119.97C7b—C13b—C12b119.8 (9)
C2b—C1b—C8b120.1 (10)C7b—C13b—H10b120.09
C1b—C2b—H4b119.76C12b—C13b—H10b120.09
C1b—C2b—C3b120.5 (8)C5b—C14b—H11b116.63
H4b—C2b—C3b119.76C5b—C14b—C15b126.7 (7)
N1b—C3b—C2b120.3 (6)H11b—C14b—C15b116.63
N1b—C3b—C10b119.2 (6)C10b—C15b—C14b128.1 (7)
C2b—C3b—C10b120.4 (6)C10b—C15b—H12b115.96
N1b—C4b—C5b119.6 (6)C14b—C15b—H12b115.96
N1b—C4b—C12b119.4 (6)O1a—C1a—O2a125.3 (10)
C5b—C4b—C12b120.9 (8)O1a—C1a—C2a111.8 (7)
C4b—C5b—C6b117.1 (7)O2a—C1a—C2a123.0 (9)
C4b—C5b—C14b122.8 (6)C1a—C2a—H2a108.98
C6b—C5b—C14b120.0 (7)C1a—C2a—O3a112.2 (7)
C5b—C6b—H5b119.09C1a—C2a—C3a108.9 (6)
C5b—C6b—C7b121.8 (8)H2a—C2a—O3a105.39
H5b—C6b—C7b119.09H2a—C2a—C3a108.91
C6b—C7b—H6b119.95O3a—C2a—C3a112.3 (7)
C6b—C7b—C13b120.1 (8)C2a—C3a—H4a108.17
H6b—C7b—C13b119.95C2a—C3a—O4a112.3 (6)
C1b—C8b—H7b120.17C2a—C3a—C4a107.6 (6)
C1b—C8b—C9b119.7 (9)H4a—C3a—O4a108.45
H7b—C8b—C9b120.17H4a—C3a—C4a113.12
C8b—C9b—H8b119.08O4a—C3a—C4a107.3 (8)
C8b—C9b—C10b121.8 (8)C3a—C4a—O5a123.3 (9)
H8b—C9b—C10b119.08C3a—C4a—O6a112.0 (9)
C3b—C10b—C9b117.5 (8)O5a—C4a—O6a124.8 (10)
C3b—C10b—C15b123.0 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2b—H1b···C4b0.862.472.722 (9)97.60
Lattice unit-cell parameters comparisons between carbamazepine phase III, the cocrystal obtained after solvent evaporation (MOXWIG; Childs et al., 2009) and the new cocrystal obtained by liquid-assisted grinding (LAG cocrystal) top
Crystal data
Chemical formulaC19H18N2O7
Mr386.4
Cell setting, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)4.96273 (12), 9.3760 (3), 37.8971 (13)
β (°)92.959 (2)
V3)1761.03 (10)
Z4
F(000)808
µ (mm-1)0.043
Specimen shape, size (mm)Cylinder, 0.5
2θ range (°)0.5–27.9
Data collection
BeamlineID22 (ESRF)
Specimen mounting0.5 mm diameter Lindemann capillary
Data collection modeTransmission (Debye–Scherrer geometry)
Scan methodContinuous scan
Radiation typeSynchrotron 31 KeV, λ = 0.39997 Å
Binning size (2θ, °)0.0015
Refinement
R factors and goodness of fitR = 0.1207, Rwpnb = 0.1725, Rexp = 0.0732
No. of refined parameters108
Crystallographic data, profile and structural parameters for CBZ/DL-TA cocrystal obtained after Rietveld refinements top
Structurea (Å)b (Å)c (Å)β (°)V3)SymmetryReference
CBZ Phase III7.550011.18613.95492.9381176.9Monoclinic P21/nEccles et al. (2011)
MOXWIG10.300626.9725.0718104.2351365.82Monoclinic P21/cChilds et al. (2009)
LAG cocrystal4.962739.376037.897192.9591761.03Monoclinic P21/cThis work
 

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