SUPPORTING INFORMATIONStructural and Spectral Characterization of a Chromium(III) Picolinate Complex:Introducing a New Redox Reaction

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Printed in the Republic of Korea http://dx.doi.org/10.5012/jkcs.2013.57.6.1

SUPPORTING INFORMATION

Structural and Spectral Characterization of a Chromium(III) Picolinate Complex:

Introducing a New Redox Reaction

Mohammad Hakimi*

Chemistry Department, Payame Noor University, 19395-4697 Tehran, I. R. Iran.

*E-mail: [email protected]

(Received August 21, 2013; Accepted September 22, 2013)

Computing Details

Program (s) used to solve structure: SHELXS97 (Sheldrick, 1990); program (s) used to refine structure: SHELXL97 (Sheldrick, 1997).

(hkm015cr)

Crystal Data C

₁₈

H

₁₄

CrN

₃

O

₇

M

_r

= 436.32 Monoclinic, C2/c a = 30.143 (7) Å b = 8.4769 (19) Å c = 13.870 (3) Å β = 95.479 (3)°

V = 3528.0 (14) Å

³

Z = 8

F(000) = 1784 D

x

= 1.643 Mg mc

³

Mo K

α radiation, λ = 0.71073 Å

µ = 0.70 mm

⁻¹

T = 296 K

0.20 × 0.10 × 0.10 mm

Data Collection

Radiation source: fine-focus sealed tube graphite

8031 measured reflections 3053 independent reflections 2276 reflections with I > 2 σ(I) R

_int

= 0.048

θ

max

= 24.8

^o

, θ

min

= 1.4

^o

h = −30→35

k = −9→10 l = −14→16

Refinement Refinement on F

²

Least-squares matrix: full R[F

²

> 2 σ(F

²

)] = 0.038 wR(F

²

) = 0.112

S = 1.10 3053 reflections 270 parameters 0 restraints

Primary atom site location: structure-invariant direct methods Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H atoms treated by a mixture of independent and con-

strained refinement

w = 1/[ σ

²

(F

_o²

) + (0.0453P)

²

+ 4.9735P]

where P = (F

o2

+ 2F

c2

)/3 ( ∆/σ)

max

< 0.001

∆ρ

max

= 0.30 e Å

⁻³

∆ρ

min

= −0.35 e Å

⁻³

Special Details

Geometry: All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement: Refinement of F

²

against ALL reflections.

The weighted R-factor wR and goodness of fit S are based on F

²

, conventional R-factors R are based on F, with F set to zero for negative F

²

. The threshold expression of F

²

>

2sigma (F

²

) is used only for calculating R-factors (gt) etc.

and is not relevant to the choice of reflections for refine-

ment. R-factors based on F

²

are statistically about twice as

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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 (Å

²

)

x y z Uiso*/Ueq

Cr1 0.112775 (18) 0.28233 (7) 0.12580 (4) 0.01405 (18)

O1 0.11514 (8) 0.2819 (3) 0.26705 (16) 0.0180 (6)

C1 0.15073 (12) 0.3390 (4) 0.3135 (3) 0.0178 (8)

O2 0.16055 (9) 0.3295 (3) 0.40078 (18) 0.0271 (7)

C2 0.18124 (11) 0.4258 (4) 0.2521 (2) 0.0154 (8)

N1 0.16787 (9) 0.4246 (3) 0.1559 (2) 0.0150 (7)

C3 0.19248 (12) 0.5033 (4) 0.0963 (3) 0.0200 (9)

H3A 0.1835 0.5033 0.0303 0.024*

C4 0.23039 (12) 0.5840 (5) 0.1288 (3) 0.0255 (9)

H4A 0.2464 0.6397 0.0859 0.031*

C5 0.24441 (12) 0.5808 (5) 0.2271 (3) 0.0252 (9)

H5A 0.2704 0.6324 0.2508 0.030*

C6 0.21945 (12) 0.5005 (4) 0.2891 (3) 0.0202 (8)

H6A 0.2284 0.4970 0.3551 0.024*

O3 0.15236 (8) 0.1005 (3) 0.13058 (17) 0.0175 (6)

C7 0.16927 (11) 0.0589 (4) 0.0511 (3) 0.0171 (8)

O4 0.19952 (8) −0.0336 (3) 0.04522 (18) 0.0252 (6)

C8 0.14751 (11) 0.1408 (4) −0.0387 (3) 0.0159 (8)

N2 0.11840 (9) 0.2563 (3) −0.0198 (2) 0.0143 (7)

C9 0.09687 (12) 0.3336 (4) −0.0950 (3) 0.0164 (8)

H9A 0.0766 0.4122 −0.0830 0.020*

C10 0.10406 (12) 0.2992 (4) −0.1898 (3) 0.0196 (8)

H10A 0.0887 0.3541 −0.2406 0.023*

C11 0.13407 (12) 0.1833 (4) −0.2085 (3) 0.0214 (9)

H11A 0.1395 0.1600 −0.2718 0.026*

C12 0.15606 (12) 0.1017 (5) −0.1312 (3) 0.0205 (9)

H12A 0.1762 0.0221 −0.1419 0.025*

O5 0.07266 (7) 0.4637 (3) 0.10998 (17) 0.0174 (6)

C13 0.03003 (12) 0.4395 (4) 0.1153 (2) 0.0163 (8)

O6 0.00209 (8) 0.5426 (3) 0.1170 (2) 0.0262 (6)

C14 0.01801 (11) 0.2671 (4) 0.1198 (2) 0.0157 (8)

N3 0.05288 (9) 0.1675 (3) 0.1181 (2) 0.0140 (7)

C15 0.04564 (12) 0.0115 (4) 0.1202 (2) 0.0177 (8)

H15A 0.0696 −0.0572 0.1183 0.021*

C16 0.00320 (12) −0.0495 (5) 0.1250 (3) 0.0203 (9)

H16A −0.0013 −0.1580 0.1262 0.024*

C17 −0.03238 (12) 0.0528 (5) 0.1280 (3) 0.0223 (9)

H17A −0.0610 0.0138 0.1319 0.027*

C18 −0.02494 (12) 0.2136 (5) 0.1251 (2) 0.0190 (8)

H18A −0.0484 0.2844 0.1266 0.023*

O7 0.10957 (10) 0.7571 (4) 0.0529 (2) 0.0302 (7)

H7A 0.1291 (17) 0.728 (6) 0.001 (4) 0.069 (17)*

H7B 0.0970 (17) 0.666 (6) 0.061 (4) 0.063 (18)*

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Atomic displacement parameters (Å

²

)

Geometric parameters (Å, º)

U¹¹ U²² U³³ U¹² U¹³ U²³

Cr1 0.0125 (3) 0.0165 (3) 0.0131 (3) −0.0005 (3) 0.0007 (2) −0.0002 (3) O1 0.0163 (13) 0.0236 (14) 0.0142 (13) −0.0037 (11) 0.0014 (10) −0.0013 (11)

C1 0.023 (2) 0.016 (2) 0.015 (2) 0.0019 (16) 0.0016 (16) −0.0022 (16)

O2 0.0320 (16) 0.0356 (17) 0.0131 (14) −0.0069 (13) −0.0003 (12) 0.0011 (12) C2 0.0165 (19) 0.015 (2) 0.0145 (19) 0.0028 (16) 0.0023 (15) −0.0033 (15) N1 0.0128 (15) 0.0164 (17) 0.0159 (16) 0.0011 (13) 0.0018 (13) 0.0012 (13)

C3 0.020 (2) 0.024 (2) 0.016 (2) 0.0004 (17) 0.0015 (16) 0.0056 (17)

C4 0.022 (2) 0.025 (2) 0.030 (2) −0.0027 (18) 0.0088 (18) 0.0037 (18)

C5 0.016 (2) 0.029 (2) 0.030 (2) −0.0041 (17) 0.0002 (18) −0.0017 (18)

C6 0.021 (2) 0.022 (2) 0.017 (2) 0.0017 (17) −0.0020 (16) −0.0026 (16)

O3 0.0188 (13) 0.0180 (14) 0.0155 (14) 0.0011 (11) 0.0009 (11) 0.0015 (11) C7 0.0144 (19) 0.018 (2) 0.018 (2) −0.0030 (16) 0.0000 (16) 0.0031 (16) O4 0.0202 (14) 0.0272 (16) 0.0273 (16) 0.0104 (13) −0.0015 (11) −0.0008 (13) C8 0.0144 (19) 0.017 (2) 0.0160 (19) −0.0016 (16) 0.0007 (15) −0.0010 (16) N2 0.0112 (15) 0.0141 (17) 0.0170 (16) −0.0016 (12) −0.0007 (12) 0.0000 (13) C9 0.0185 (19) 0.0124 (19) 0.017 (2) 0.0005 (15) −0.0015 (15) 0.0007 (15) C10 0.021 (2) 0.020 (2) 0.0161 (19) 0.0060 (17) −0.0045 (15) 0.0012 (16)

C11 0.023 (2) 0.026 (2) 0.015 (2) 0.0067 (17) 0.0038 (16) −0.0046 (17)

C12 0.0170 (19) 0.023 (2) 0.022 (2) 0.0017 (17) 0.0037 (16) −0.0033 (17) O5 0.0147 (13) 0.0166 (14) 0.0212 (14) −0.0005 (11) 0.0032 (10) −0.0020 (11) C13 0.0150 (19) 0.022 (2) 0.0115 (19) −0.0003 (17) 0.0010 (15) −0.0020 (15) O6 0.0190 (15) 0.0214 (16) 0.0385 (17) 0.0043 (12) 0.0051 (12) −0.0037 (13) C14 0.0151 (18) 0.018 (2) 0.0133 (18) 0.0004 (16) 0.0011 (14) −0.0014 (15) N3 0.0136 (16) 0.0162 (17) 0.0122 (16) 0.0005 (13) 0.0003 (12) 0.0005 (13) C15 0.020 (2) 0.018 (2) 0.0146 (19) 0.0036 (16) 0.0021 (15) −0.0002 (16) C16 0.027 (2) 0.016 (2) 0.017 (2) −0.0044 (17) −0.0024 (16) 0.0022 (16) C17 0.018 (2) 0.032 (2) 0.017 (2) −0.0070 (18) 0.0007 (16) −0.0006 (17) C18 0.0157 (19) 0.023 (2) 0.018 (2) 0.0002 (17) 0.0004 (15) −0.0023 (17) O7 0.0330 (17) 0.0233 (18) 0.0359 (18) −0.0004 (14) 0.0118 (14) −0.0060 (14)

Cr1—O3 1.946 (2) N2—C9 1.345 (4)

Cr1—O1 1.954 (2) C9—C10 1.384 (5)

Cr1—O5 1.956 (2) C9—H9A 0.9300

Cr1—N3 2.045 (3) C10—C11 1.377 (5)

Cr1—N2 2.054 (3) C10—H10A 0.9300

Cr1—N1 2.062 (3) C11—C12 1.390 (5)

O1—C1 1.292 (4) C11—H11A 0.9300

C1—O2 1.221 (4) C12—H12A 0.9300

C1—C2 1.504 (5) O5—C13 1.311 (4)

C2—N1 1.357 (4) C13—O6 1.216 (4)

C2—C6 1.370 (5) C13—C14 1.508 (5)

N1—C3 1.339 (4) C14—N3 1.351 (4)

C3—C4 1.371 (5) C14—C18 1.380 (5)

C3—H3A 0.9300 N3—C15 1.340 (5)

C4—C5 1.388 (5) C15—C16 1.388 (5)

C4—H4A 0.9300 C15—H15A 0.9300

C5—C6 1.376 (5) C16—C17 1.383 (5)

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C5—H5A 0.9300 C16—H16A 0.9300

C6—H6A 0.9300 C17—C18 1.383 (5)

O3—C7 1.307 (4) C17—H17A 0.9300

C7—O4 1.211 (4) C18—H18A 0.9300

C7—C8 1.519 (5) O7—H7A 1.00 (6)

C8—N2 1.358 (4) O7—H7B 0.87 (5)

C8—C12 1.373 (5)

O3—Cr1—O1 90.04 (10) N2—C8—C12 122.5 (3)

O3—Cr1—O5 175.53 (10) N2—C8—C7 114.0 (3)

O1—Cr1—O5 94.42 (10) C12—C8—C7 123.4 (3)

O3—Cr1—N3 99.21 (11) C9—N2—C8 118.3 (3)

O1—Cr1—N3 89.93 (10) C9—N2—Cr1 129.1 (2)

O5—Cr1—N3 80.52 (11) C8—N2—Cr1 112.5 (2)

O3—Cr1—N2 80.83 (10) N2—C9—C10 121.8 (3)

O1—Cr1—N2 170.74 (11) N2—C9—H9A 119.1

O5—Cr1—N2 94.72 (10) C10—C9—H9A 119.1

N3—Cr1—N2 93.04 (11) C11—C10—C9 119.6 (3)

O3—Cr1—N1 88.67 (11) C11—C10—H10A 120.2

O1—Cr1—N1 81.19 (10) C9—C10—H10A 120.2

O5—Cr1—N1 92.30 (11) C10—C11—C12 118.9 (4)

N3—Cr1—N1 168.16 (12) C10—C11—H11A 120.6

N2—Cr1—N1 96.95 (11) C12—C11—H11A 120.6

C1—O1—Cr1 116.7 (2) C8—C12—C11 118.9 (4)

O2—C1—O1 125.5 (3) C8—C12—H12A 120.6

O2—C1—C2 119.3 (3) C11—C12—H12A 120.6

O1—C1—C2 115.1 (3) C13—O5—Cr1 118.0 (2)

N1—C2—C6 122.1 (3) O6—C13—O5 125.0 (3)

N1—C2—C1 114.4 (3) O6—C13—C14 121.8 (3)

C6—C2—C1 123.5 (3) O5—C13—C14 113.3 (3)

C3—N1—C2 118.2 (3) N3—C14—C18 122.1 (3)

C3—N1—Cr1 130.5 (2) N3—C14—C13 114.5 (3)

C2—N1—Cr1 111.2 (2) C18—C14—C13 123.4 (3)

N1—C3—C4 122.6 (3) C15—N3—C14 119.2 (3)

N1—C3—H3A 118.7 C15—N3—Cr1 127.8 (2)

C4—C3—H3A 118.7 C14—N3—Cr1 112.7 (2)

C3—C4—C5 118.7 (4) N3—C15—C16 121.4 (3)

C3—C4—H4A 120.7 N3—C15—H15A 119.3

C5—C4—H4A 120.7 C16—C15—H15A 119.3

C6—C5—C4 119.3 (4) C17—C16—C15 119.3 (4)

C6—C5—H5A 120.3 C17—C16—H16A 120.4

C4—C5—H5A 120.3 C15—C16—H16A 120.4

C2—C6—C5 119.0 (3) C16—C17—C18 119.3 (3)

C2—C6—H6A 120.5 C16—C17—H17A 120.4

C5—C6—H6A 120.5 C18—C17—H17A 120.4

C7—O3—Cr1 118.2 (2) C14—C18—C17 118.8 (3)

O4—C7—O3 126.0 (3) C14—C18—H18A 120.6

O4—C7—C8 120.7 (3) C17—C18—H18A 120.6

O3—C7—C8 113.3 (3) H7A—O7—H7B 100 (4)

O3—Cr1—O1—C1 O5—Cr1—O1—C1 N3—Cr1—O1—C1

77.2 (3)

−103.1 (3) 176.4 (3)

O1—Cr1—N2—C9 O5—Cr1—N2—C9 N3—Cr1—N2—C9

−176.4 (6)

−5.7 (3) 75.0 (3)

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N2—Cr1—O1—C1 N1—Cr1—O1—C1 Cr1—O1—C1—O2

67.7 (7)

−11.4 (2)

−169.8 (3)

N1—Cr1—N2—C9 O3—Cr1—N2—C8 O1—Cr1—N2—C8

−98.6 (3)

−4.3 (2) 5.4 (8)

Cr1—O1—C1—C2 11.3 (4) O5—Cr1—N2—C8 176.1 (2)

O2—C1—C2—N1 O1—C1—C2—N1 O2—C1—C2—C6 O1—C1—C2—C6 C6—C2—N1—C3 C1—C2—N1—C3

177.9 (3)

−3.1 (4)

−2.1 (5) 176.9 (3)

−2.0 (5) 178.0 (3)

N3—Cr1—N2—C8 N1—Cr1—N2—C8 C8—N2—C9—C10 Cr1—N2—C9—C10 N2—C9—C10—C11 C9—C10—C11—C12

−103.1 (2) 83.2 (2)

−0.7 (5)

−178.8 (2)

−0.1 (5) 0.9 (5) C6—C2—N1—Cr1

C1—C2—N1—Cr1 O3—Cr1—N1—C3 O1—Cr1—N1—C3 O5—Cr1—N1—C3 N3—Cr1—N1—C3

174.1 (3)

−5.9 (4) 94.3 (3)

−175.5 (3)

−81.3 (3)

−133.6 (5)

N2—C8—C12—C11 C7—C8—C12—C11 C10—C11—C12—C8 O3—Cr1—O5—C13 O1—Cr1—O5—C13 N3—Cr1—O5—C13

−0.1 (5) 179.5 (3)

−0.8 (5) 96.1 (13)

−80.1 (2) 9.1 (2) N2—Cr1—N1—C3

O3—Cr1—N1—C2 O1—Cr1—N1—C2

13.7 (3)

−81.2 (2) 9.0 (2)

N2—Cr1—O5—C13 N1—Cr1—O5—C13 Cr1—O5—C13—O6

101.4 (2)

−161.4 (2) 172.0 (3)

O5—Cr1—N1—C2 103.2 (2) Cr1—O5—C13—C14 −7.9 (4)

N3—Cr1—N1—C2 N2—Cr1—N1—C2

50.9 (7)

−161.8 (2)

O6—C13—C14—N3 O5—C13—C14—N3

−179.5 (3) 0.4 (4) C2—N1—C3—C4

Cr1—N1—C3—C4 N1—C3—C4—C5 C3—C4—C5—C6 N1—C2—C6—C5 C1—C2—C6—C5

0.2 (5)

−175.1 (3) 1.6 (6)

−1.6 (6) 1.9 (5)

−178.0 (3)

O6—C13—C14—C18 O5—C13—C14—C18 C18—C14—N3—C15 C13—C14—N3—C15 C18—C14—N3—Cr1 C13—C14—N3—Cr1

0.6 (5)

−179.5 (3) 1.0 (5)

−178.9 (3)

−173.4 (3) 6.7 (4) C4—C5—C6—C2

O1—Cr1—O3—C7

−0.1 (6)

−169.1 (2)

O3—Cr1—N3—C15 O1—Cr1—N3—C15

2.4 (3)

−87.7 (3)

O5—Cr1—O3—C7 14.7 (14) O5—Cr1—N3—C15 177.8 (3)

N3—Cr1—O3—C7 100.9 (2) N2—Cr1—N3—C15 83.6 (3)

N2—Cr1—O3—C7 9.3 (2) N1—Cr1—N3—C15 −128.9 (5)

N1—Cr1—O3—C7 −87.9 (2) O3—Cr1—N3—C14 176.2 (2)

Cr1—O3—C7—O4 167.3 (3) O1—Cr1—N3—C14 86.2 (2)

Cr1—O3—C7—C8 −11.9 (4) O5—Cr1—N3—C14 −8.3 (2)

O4—C7—C8—N2 −171.5 (3) N2—Cr1—N3—C14 −102.6 (2)

O3—C7—C8—N2 7.7 (4) N1—Cr1—N3—C14 44.9 (7)

O4—C7—C8—C12 8.8 (5) C14—N3—C15—C16 −0.6 (5)

O3—C7—C8—C12 −171.9 (3) Cr1—N3—C15—C16 172.8 (2)

C12—C8—N2—C9 0.8 (5) N3—C15—C16—C17 −0.2 (5)

C7—C8—N2—C9 −178.8 (3) C15—C16—C17—C18 0.7 (5)

C12—C8—N2—Cr1 179.2 (3) N3—C14—C18—C17 −0.5 (5)

C7—C8—N2—Cr1 −0.4 (4) C13—C14—C18—C17 179.4 (3)

O3—Cr1—N2—C9 173.9 (3) C16—C17—C18—C14 −0.4 (5)

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Figure S1. FT-IR spectrum.

Figure S2. Raman spectrum.

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checkCIF/PLATON report

Structure factors have been supplied for datablock (s) hkm015cr No syntax errors found. CIF dictionary Interpreting this report

Alert level C

Datablock: hkm015cr

Bond precision C−C = 0.0055 A Wavelength = 0.71073

Cell a = 30.143(7) b = 8.4769(19) c = 13.870(3)

alpha = 90 beta = 95.479(3) gamma = 90

Temperature 296 K

Calculated Reported

Volume 3527.9(14) 3528.0(14)

Space group C 2/c C2/c

Hall group −C 2yc ?

Moiety formula C₁₈H₁₂CrN₃O₆, H₂O ?

Sum formula C₁₈H₁₄CrN₃O₇ C₁₈H₁₄CrN₃O₇

Mr 436.32 436.32

Dx, g cm⁻³ 1.643 1.643

Z 8 8

Mu (mm⁻¹) 0.699 0.699

F000 1784.0 1784.0

F000’ 1787.46

h, k, lmax 35, 10, 16 35, 10, 16

Nref 3059 3053

Tmin, Tmax 0.920, 0.932 0.873, 0.933

Tmin’ 0.870

Correction method = ?

Data completeness = 0.998 Theta(max) = 24.840

R(reflections) = 0.0380(2276) wR2(reflections) = 0.1116( 3053)

S = 1.096 Npar = 270

The following ALERTS were generated. Each ALERT has the format test-name_ALERT_alert-type_alert-level.

Click on the hyperlinks for more details of the test.

PLAT052_ALERT_1_C Info on Absorption Correction Method Missing ... ? Do !

Alert level G

PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF ? Do !

PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 4

N2 -CR1 -O1 -C1 67.70 0.70 1.555 1.555 1.555 1.555

O5 -CR1 -O3 -C7 14.70 1.40 1.555 1.555 1.555 1.555

O1 -CR1 -N2 -C9 -176.40 0.60 1.555 1.555 1.555 1.555

O1 -CR1 -N2 -C8 5.40 0.80 1.555 1.555 1.555 1.555

O3 -CR1 -O5 -C13 96.10 1.30 1.555 1.555 1.555 1.555

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It is advisable to attempt to resolve as many as possible of the alerts in all categories. Often the minor alerts point to easily fixed oversights, errors and omissions in your CIF or refinement strategy, so attention to these fine details can be worthwhile. In order to resolve some of the more serious problems it may be necessary to carry out additional measure- ments or structure refinements. However, the purpose of your study may justify the reported deviations and the more serious of these should normally be commented upon in the discussion or experimental section of a paper or in the "special_

details" fields of the CIF. checkCIF was carefully designed to identify outliers and unusual parameters, but every test has its limitations and alerts that are not important in a par- ticular case may appear. Conversely, the absence of alerts does not guarantee there are no aspects of the results need- ing attention. It is up to the individual to critically assess

their own results and, if necessary, seek expert advice.

Publication of your CIF in IUCr journals

A basic structural check has been run on your CIF.

These basic checks will be run on all CIFs submitted for publication in IUCr journals (Acta Crystallographica, Journal of Applied Crystallography, Journal of Synchro- tron Radiation); however, if you intend to submit to Acta Crystallographica Section C or E, you should make sure that full publication checks are run on the final version of your CIF prior to submission.

Publication of your CIF in other journals

Please refer to the Notes for Authors of the relevant jour- nal for any special instructions relating to CIF submission.

0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 6 ALERT level G = General information/check it is not something unexpected 1 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 0 ALERT type 3 Indicator that the structure quality may be low

5 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check