Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027365/lh2409sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027365/lh2409Isup2.hkl |
CCDC reference: 654978
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.032
- wR factor = 0.081
- Data-to-parameter ratio = 39.4
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.338 0.507 Tmin and Tmax expected: 0.257 0.462 RR = 1.197 Please check that your absorption correction is appropriate. PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.21 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.91 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.30 PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. Cl1 .. 3.58 Ang.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.911 Tmax scaled 0.462 Tmin scaled 0.308 REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 37.50 From the CIF: _reflns_number_total 6780 Count of symmetry unique reflns 3572 Completeness (_total/calc) 189.81% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3208 Fraction of Friedel pairs measured 0.898 Are heavy atom types Z>Si present yes PLAT033_ALERT_2_G Flack Parameter Value Deviates 2 * su from zero. 0.06 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For general background and related literature, see: Uchida et al. (1998); Watson et al. (1993); Patil, Dharmaprakash et al. (2006). For our previous work on related compounds, see: Patil, Teh, Fun, Babu et al. (2007); Patil, Teh, Fun, Razak et al. (2007).
The experimental procedure is comparable with that reported previously (Patil, Teh, Fun, Babu et al.,2007; Patil, Teh, Fun, Razak et al., 2007). The actual quantities used for preparation of (I) were: 2-chloro-6-fluorobenzaldehyde (0.01 mol), 4-bromoacetophenone (0.01 mol), methanol 960 ml) and 5 ml of 10% of NaOH aqueous solution. Crystal suitable for X-ray analysis were grown by slow evaporation of an acetone solution at room temperature.
All H atoms were refined using a riding model, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C).
Chalcones with appropriate subtituents are a class of nonlinear optical materials (Patil et al., 2006; Patil, Dharmaprakash et al., 2007). As a part of our on-going work on the synthesis and structure determination of subtituted chalcones (Patil, Teh, Fun, Babu et al., 2007, Patil, Teh, Fun, Razak et al., 2007) the crystal structure of the title compound (I) was determined (Fig. 1). The title compound can potentially exhibit second-order NLO properties as it crystallizes in a non-centrosymmetric space group.
All bond lengths and angles in (I) show normal values (Allen et al., 1987) and are comparable to those of a related structure (Patil, Teh, Fun, Babu et al.,2007; Patil, Teh, Fun, Razak et al., 2007). The dihedral angle between the benzene rings is 22.7 (1)°. The least-squares plane through the enone group (O1/C7–C9) makes dihedral angles of 13.6 (1) and 9.4 (1)° with the C1–C6 and C10–C15 benzene rings, respectively.
Three intramolecular hydrogen bonds are observed in the molecular structure (Table 1). The intramolecular structure generates S(5) ring motifs for the C9—H9A···O1 and C9—H9A···Cl1 interactions and an S(6) ring motif for an C8—H8A···F1 interaction (Bernstein et al., 1995). The molecules are stacked along the b axis and the structure is stabilized by C4—H4A···F1i intermolecular interactions. Short Br1···Cl1(1 - x, 2 - y, -1/2 + z) contacts [3.579 (1) Å] also contribute to the stabilization of the crystal structure.
For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For general background and related literature, see: Uchida et al. (1998); Watson et al. (1993); Patil, Dharmaprakash et al. (2006). For our previous work on related compounds, see: Patil, Teh, Fun, Babu et al. (2007); Patil, Teh, Fun, Razak et al. (2007).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
C15H9BrClFO | F(000) = 672 |
Mr = 339.58 | Dx = 1.729 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 8121 reflections |
a = 27.8814 (4) Å | θ = 2.3–37.5° |
b = 3.9300 (1) Å | µ = 3.35 mm−1 |
c = 11.9065 (2) Å | T = 100 K |
V = 1304.64 (4) Å3 | Block, colourless |
Z = 4 | 0.59 × 0.35 × 0.23 mm |
Bruker SMART APEXII CCD area-detector diffractometer | 6780 independent reflections |
Radiation source: fine-focus sealed tube | 5407 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
Detector resolution: 8.33 pixels mm-1 | θmax = 37.5°, θmin = 1.5° |
ω scans | h = −47→46 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −6→6 |
Tmin = 0.338, Tmax = 0.507 | l = −20→19 |
31202 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.081 | w = 1/[σ2(Fo2) + (0.0227P)2 + 0.4581P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
6780 reflections | Δρmax = 0.69 e Å−3 |
172 parameters | Δρmin = −0.30 e Å−3 |
1 restraint | Absolute structure: Flack (1983), with 3224 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.057 (6) |
C15H9BrClFO | V = 1304.64 (4) Å3 |
Mr = 339.58 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 27.8814 (4) Å | µ = 3.35 mm−1 |
b = 3.9300 (1) Å | T = 100 K |
c = 11.9065 (2) Å | 0.59 × 0.35 × 0.23 mm |
Bruker SMART APEXII CCD area-detector diffractometer | 6780 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 5407 reflections with I > 2σ(I) |
Tmin = 0.338, Tmax = 0.507 | Rint = 0.047 |
31202 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.081 | Δρmax = 0.69 e Å−3 |
S = 1.05 | Δρmin = −0.30 e Å−3 |
6780 reflections | Absolute structure: Flack (1983), with 3224 Friedel pairs |
172 parameters | Absolute structure parameter: 0.057 (6) |
1 restraint |
Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment. |
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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.338269 (6) | 1.70184 (5) | 0.72708 (2) | 0.02248 (5) | |
Cl1 | 0.684369 (18) | 0.41618 (14) | 0.93374 (4) | 0.02392 (10) | |
F1 | 0.62050 (5) | 0.9222 (4) | 0.57020 (10) | 0.0244 (3) | |
O1 | 0.54265 (6) | 1.0720 (5) | 0.95820 (13) | 0.0264 (3) | |
C1 | 0.47189 (7) | 1.2413 (5) | 0.70906 (16) | 0.0180 (4) | |
H1A | 0.4909 | 1.1394 | 0.6544 | 0.022* | |
C2 | 0.42735 (7) | 1.3755 (5) | 0.67974 (18) | 0.0197 (3) | |
H2A | 0.4163 | 1.3642 | 0.6061 | 0.024* | |
C3 | 0.39995 (7) | 1.5256 (5) | 0.76281 (17) | 0.0178 (3) | |
C4 | 0.41570 (7) | 1.5506 (5) | 0.87334 (17) | 0.0196 (4) | |
H4A | 0.3968 | 1.6558 | 0.9275 | 0.024* | |
C5 | 0.45975 (7) | 1.4168 (5) | 0.90101 (17) | 0.0190 (3) | |
H5A | 0.4707 | 1.4320 | 0.9746 | 0.023* | |
C6 | 0.48825 (7) | 1.2585 (5) | 0.82009 (16) | 0.0160 (3) | |
C7 | 0.53423 (7) | 1.1020 (5) | 0.85802 (16) | 0.0174 (3) | |
C8 | 0.56942 (7) | 0.9878 (5) | 0.77217 (17) | 0.0188 (3) | |
H8A | 0.5645 | 1.0334 | 0.6964 | 0.023* | |
C9 | 0.60856 (7) | 0.8172 (5) | 0.80645 (16) | 0.0168 (3) | |
H9A | 0.6100 | 0.7720 | 0.8830 | 0.020* | |
C10 | 0.64912 (6) | 0.6927 (5) | 0.74095 (18) | 0.0167 (3) | |
C11 | 0.68697 (7) | 0.5114 (5) | 0.79113 (17) | 0.0190 (3) | |
C12 | 0.72672 (6) | 0.3974 (5) | 0.7325 (2) | 0.0236 (3) | |
H12A | 0.7509 | 0.2791 | 0.7694 | 0.028* | |
C13 | 0.73008 (8) | 0.4611 (6) | 0.6183 (2) | 0.0259 (4) | |
H13A | 0.7567 | 0.3860 | 0.5784 | 0.031* | |
C14 | 0.69366 (8) | 0.6376 (6) | 0.56320 (19) | 0.0238 (4) | |
H14A | 0.6954 | 0.6803 | 0.4865 | 0.029* | |
C15 | 0.65495 (7) | 0.7471 (5) | 0.62546 (19) | 0.0198 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.01427 (7) | 0.02028 (8) | 0.03290 (9) | 0.00260 (6) | −0.00130 (9) | −0.00051 (11) |
Cl1 | 0.0223 (2) | 0.0247 (2) | 0.0248 (2) | 0.00264 (17) | −0.00752 (18) | 0.00313 (18) |
F1 | 0.0225 (6) | 0.0322 (7) | 0.0186 (5) | 0.0032 (5) | −0.0009 (4) | 0.0036 (5) |
O1 | 0.0253 (7) | 0.0362 (9) | 0.0177 (7) | 0.0073 (7) | −0.0018 (5) | 0.0010 (6) |
C1 | 0.0159 (7) | 0.0196 (9) | 0.0186 (10) | 0.0026 (5) | 0.0006 (6) | −0.0008 (6) |
C2 | 0.0165 (8) | 0.0233 (10) | 0.0194 (8) | 0.0013 (6) | −0.0011 (6) | −0.0007 (7) |
C3 | 0.0141 (7) | 0.0163 (8) | 0.0230 (8) | −0.0004 (6) | 0.0002 (6) | 0.0014 (6) |
C4 | 0.0184 (8) | 0.0197 (9) | 0.0206 (9) | 0.0012 (6) | 0.0044 (6) | −0.0028 (7) |
C5 | 0.0191 (8) | 0.0205 (9) | 0.0173 (8) | 0.0003 (7) | 0.0008 (6) | −0.0020 (6) |
C6 | 0.0152 (7) | 0.0160 (9) | 0.0167 (8) | 0.0003 (6) | 0.0014 (6) | 0.0002 (6) |
C7 | 0.0158 (7) | 0.0188 (9) | 0.0175 (8) | 0.0009 (6) | −0.0014 (6) | 0.0003 (6) |
C8 | 0.0166 (8) | 0.0222 (9) | 0.0175 (8) | 0.0025 (6) | −0.0002 (6) | 0.0013 (6) |
C9 | 0.0155 (8) | 0.0169 (8) | 0.0181 (8) | 0.0005 (6) | 0.0000 (6) | 0.0007 (6) |
C10 | 0.0126 (6) | 0.0164 (7) | 0.0212 (10) | −0.0017 (5) | −0.0015 (6) | −0.0002 (6) |
C11 | 0.0159 (8) | 0.0160 (8) | 0.0252 (9) | −0.0013 (6) | −0.0025 (6) | −0.0004 (6) |
C12 | 0.0139 (7) | 0.0184 (7) | 0.0384 (10) | 0.0005 (5) | −0.0014 (9) | −0.0013 (10) |
C13 | 0.0170 (8) | 0.0227 (10) | 0.0380 (11) | −0.0037 (7) | 0.0069 (8) | −0.0069 (8) |
C14 | 0.0230 (9) | 0.0231 (11) | 0.0252 (10) | −0.0023 (7) | 0.0059 (8) | −0.0040 (7) |
C15 | 0.0176 (8) | 0.0189 (10) | 0.0229 (9) | −0.0012 (6) | 0.0001 (6) | −0.0007 (6) |
Br1—C3 | 1.9021 (19) | C7—C8 | 1.486 (3) |
Cl1—C11 | 1.740 (2) | C8—C9 | 1.344 (3) |
F1—C15 | 1.353 (3) | C8—H8A | 0.9300 |
O1—C7 | 1.221 (2) | C9—C10 | 1.458 (3) |
C1—C2 | 1.394 (3) | C9—H9A | 0.9300 |
C1—C6 | 1.400 (3) | C10—C15 | 1.401 (3) |
C1—H1A | 0.9300 | C10—C11 | 1.407 (3) |
C2—C3 | 1.382 (3) | C11—C12 | 1.384 (3) |
C2—H2A | 0.9300 | C12—C13 | 1.385 (4) |
C3—C4 | 1.391 (3) | C12—H12A | 0.9300 |
C4—C5 | 1.376 (3) | C13—C14 | 1.394 (3) |
C4—H4A | 0.9300 | C13—H13A | 0.9300 |
C5—C6 | 1.395 (3) | C14—C15 | 1.378 (3) |
C5—H5A | 0.9300 | C14—H14A | 0.9300 |
C6—C7 | 1.492 (3) | ||
C2—C1—C6 | 120.57 (18) | C7—C8—H8A | 120.7 |
C2—C1—H1A | 119.7 | C8—C9—C10 | 129.38 (19) |
C6—C1—H1A | 119.7 | C8—C9—H9A | 115.3 |
C3—C2—C1 | 118.35 (19) | C10—C9—H9A | 115.3 |
C3—C2—H2A | 120.8 | C15—C10—C11 | 114.03 (18) |
C1—C2—H2A | 120.8 | C15—C10—C9 | 124.31 (18) |
C2—C3—C4 | 122.19 (18) | C11—C10—C9 | 121.64 (19) |
C2—C3—Br1 | 119.68 (15) | C12—C11—C10 | 123.4 (2) |
C4—C3—Br1 | 118.12 (15) | C12—C11—Cl1 | 117.14 (17) |
C5—C4—C3 | 118.77 (18) | C10—C11—Cl1 | 119.48 (16) |
C5—C4—H4A | 120.6 | C11—C12—C13 | 119.4 (2) |
C3—C4—H4A | 120.6 | C11—C12—H12A | 120.3 |
C4—C5—C6 | 120.89 (18) | C13—C12—H12A | 120.3 |
C4—C5—H5A | 119.6 | C12—C13—C14 | 120.18 (19) |
C6—C5—H5A | 119.6 | C12—C13—H13A | 119.9 |
C5—C6—C1 | 119.21 (18) | C14—C13—H13A | 119.9 |
C5—C6—C7 | 117.66 (17) | C15—C14—C13 | 118.2 (2) |
C1—C6—C7 | 123.08 (17) | C15—C14—H14A | 120.9 |
O1—C7—C8 | 121.04 (18) | C13—C14—H14A | 120.9 |
O1—C7—C6 | 120.04 (18) | F1—C15—C14 | 117.0 (2) |
C8—C7—C6 | 118.92 (16) | F1—C15—C10 | 118.21 (18) |
C9—C8—C7 | 118.54 (18) | C14—C15—C10 | 124.8 (2) |
C9—C8—H8A | 120.7 | ||
C6—C1—C2—C3 | 0.1 (3) | C8—C9—C10—C15 | 2.9 (3) |
C1—C2—C3—C4 | 0.9 (3) | C8—C9—C10—C11 | −178.8 (2) |
C1—C2—C3—Br1 | −178.45 (15) | C15—C10—C11—C12 | 0.3 (3) |
C2—C3—C4—C5 | −1.0 (3) | C9—C10—C11—C12 | −178.12 (18) |
Br1—C3—C4—C5 | 178.43 (15) | C15—C10—C11—Cl1 | −178.71 (15) |
C3—C4—C5—C6 | 0.0 (3) | C9—C10—C11—Cl1 | 2.8 (3) |
C4—C5—C6—C1 | 1.0 (3) | C10—C11—C12—C13 | −0.2 (3) |
C4—C5—C6—C7 | −176.51 (19) | Cl1—C11—C12—C13 | 178.82 (16) |
C2—C1—C6—C5 | −1.0 (3) | C11—C12—C13—C14 | −0.2 (3) |
C2—C1—C6—C7 | 176.34 (19) | C12—C13—C14—C15 | 0.5 (3) |
C5—C6—C7—O1 | 10.4 (3) | C13—C14—C15—F1 | 179.01 (19) |
C1—C6—C7—O1 | −167.0 (2) | C13—C14—C15—C10 | −0.4 (3) |
C5—C6—C7—C8 | −169.02 (18) | C11—C10—C15—F1 | −179.39 (18) |
C1—C6—C7—C8 | 13.6 (3) | C9—C10—C15—F1 | −1.0 (3) |
O1—C7—C8—C9 | 7.1 (3) | C11—C10—C15—C14 | 0.0 (3) |
C6—C7—C8—C9 | −173.55 (18) | C9—C10—C15—C14 | 178.4 (2) |
C7—C8—C9—C10 | −176.82 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···F1i | 0.93 | 2.42 | 3.287 (2) | 155 |
C8—H8A···F1 | 0.93 | 2.21 | 2.807 (2) | 121 |
C9—H9A···Cl1 | 0.93 | 2.57 | 3.041 (2) | 112 |
C9—H9A···O1 | 0.93 | 2.39 | 2.765 (3) | 104 |
Symmetry code: (i) −x+1, −y+3, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H9BrClFO |
Mr | 339.58 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 100 |
a, b, c (Å) | 27.8814 (4), 3.9300 (1), 11.9065 (2) |
V (Å3) | 1304.64 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 3.35 |
Crystal size (mm) | 0.59 × 0.35 × 0.23 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.338, 0.507 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 31202, 6780, 5407 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.857 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.081, 1.05 |
No. of reflections | 6780 |
No. of parameters | 172 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.69, −0.30 |
Absolute structure | Flack (1983), with 3224 Friedel pairs |
Absolute structure parameter | 0.057 (6) |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SAINT, SHELXTL (Sheldrick, 1998), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···F1i | 0.93 | 2.423 | 3.287 (2) | 155 |
C8—H8A···F1 | 0.93 | 2.211 | 2.807 (2) | 121 |
C9—H9A···Cl1 | 0.93 | 2.573 | 3.041 (2) | 112 |
C9—H9A···O1 | 0.93 | 2.391 | 2.765 (3) | 104 |
Symmetry code: (i) −x+1, −y+3, z+1/2. |
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Chalcones with appropriate subtituents are a class of nonlinear optical materials (Patil et al., 2006; Patil, Dharmaprakash et al., 2007). As a part of our on-going work on the synthesis and structure determination of subtituted chalcones (Patil, Teh, Fun, Babu et al., 2007, Patil, Teh, Fun, Razak et al., 2007) the crystal structure of the title compound (I) was determined (Fig. 1). The title compound can potentially exhibit second-order NLO properties as it crystallizes in a non-centrosymmetric space group.
All bond lengths and angles in (I) show normal values (Allen et al., 1987) and are comparable to those of a related structure (Patil, Teh, Fun, Babu et al.,2007; Patil, Teh, Fun, Razak et al., 2007). The dihedral angle between the benzene rings is 22.7 (1)°. The least-squares plane through the enone group (O1/C7–C9) makes dihedral angles of 13.6 (1) and 9.4 (1)° with the C1–C6 and C10–C15 benzene rings, respectively.
Three intramolecular hydrogen bonds are observed in the molecular structure (Table 1). The intramolecular structure generates S(5) ring motifs for the C9—H9A···O1 and C9—H9A···Cl1 interactions and an S(6) ring motif for an C8—H8A···F1 interaction (Bernstein et al., 1995). The molecules are stacked along the b axis and the structure is stabilized by C4—H4A···F1i intermolecular interactions. Short Br1···Cl1(1 - x, 2 - y, -1/2 + z) contacts [3.579 (1) Å] also contribute to the stabilization of the crystal structure.