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The crystal structure of the nanocrystalline α phase of Pigment Yellow 213 (P.Y. 213) was solved by a combination of single-crystal electron diffraction and X-ray powder diffraction, despite the poor crystallinity of the material. The molecules form an efficient dense packing, which explains the observed insolubility and weather fastness of the pigment. The pair-distribution function (PDF) of the α phase is consistent with the determined crystal structure. The β phase of P.Y. 213 shows even lower crystal quality, so extracting any structural information directly from the diffraction data is not possible. PDF analysis indicates the β phase to have a columnar structure with a similar local structure as the α phase and a domain size in column direction of approximately 4 nm.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768109003759/og5034sup1.cif
Contains datablocks global, PY213

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768109003759/og5034PY213sup2.rtv
Contains datablock PY213

txt

Text file https://doi.org/10.1107/S0108768109003759/og5034sup3.txt
Powder data in .xye format

CCDC reference: 737338

Computing details top

Data collection: STOE WINXPOW (STOE & CIE GmbH, 2004); cell refinement: TOPAS (A.A.Coelho, 2007); data reduction: DASH (W.I.F.David et al., 2006); program(s) used to solve structure: DASH (W.I.F.David et al., 2006); program(s) used to refine structure: TOPAS (A.A.Coelho, 2007); molecular graphics: Mercury (C.F. Macrae et al., 2008); software used to prepare material for publication: DASH, TOPAS, Mercury.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
[Figure 11]
[Figure 12]
(PY213) top
Crystal data top
C23H21N5O9Z = 2
Mr = 511.45F(000) = 532
Triclinic, P1Dx = 1.513 Mg m3
a = 6.9006 (3) ÅSynchrotron radiation, λ = 0.40007 Å
b = 11.8347 (6) ŵ = 0.03 mm1
c = 14.0592 (7) ÅT = 293 K
α = 81.811 (4)°Particle morphology: no specific habit
β = 81.032 (9)°yellow
γ = 87.541 (10)°cylinder, 10 × 0.5 mm
V = 1122.31 (10) Å3Specimen preparation: Prepared at 293 K and 0.00 kPa
Data collection top
High resolution
diffractometer (ID31, ESRF)
Scan method: continuous
Double crystal Si 111 monochromator2θmin = 1.300°, 2θmax = 18.750°, 2θstep = 0.005°
Data collection mode: transmission
Refinement top
Refinement on Inet1375 parameters
Least-squares matrix: full with fixed elements per cycle159 restraints
Rp = 0.2610 constraints
Rwp = 0.175H-atom parameters not refined
Rexp = 0.130Weighting scheme based on measured s.u.'s w = 1/σ[Yobs]2
χ2 = 1.346
5356 data pointsBackground function: Chebyshev polynomial with 25 terms
Profile function: modified Thompson-Cox-Hastings pseudo-Voigt (Young, 1993)Preferred orientation correction: none
Crystal data top
C23H21N5O9γ = 87.541 (10)°
Mr = 511.45V = 1122.31 (10) Å3
Triclinic, P1Z = 2
a = 6.9006 (3) ÅSynchrotron radiation, λ = 0.40007 Å
b = 11.8347 (6) ŵ = 0.03 mm1
c = 14.0592 (7) ÅT = 293 K
α = 81.811 (4)°cylinder, 10 × 0.5 mm
β = 81.032 (9)°
Data collection top
High resolution
diffractometer (ID31, ESRF)
Scan method: continuous
Data collection mode: transmission2θmin = 1.300°, 2θmax = 18.750°, 2θstep = 0.005°
Refinement top
Rp = 0.2615356 data points
Rwp = 0.1751375 parameters
Rexp = 0.130159 restraints
χ2 = 1.346H-atom parameters not refined
Special details top

Experimental. specimen was rotated in its plane

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzBiso*/Beq
C10.6787 (17)0.6583 (4)0.9909 (3)4.5
C20.7340 (17)0.5427 (4)1.0186 (4)4.5
C30.6212 (17)0.7362 (4)1.0593 (4)4.5
N40.706 (3)0.7056 (5)0.8965 (4)4.5
O50.798 (4)0.4785 (8)0.9554 (6)4.5
N60.705 (2)0.4938 (4)1.1119 (3)4.5
C70.5520 (8)0.8567 (4)1.0365 (3)4.5
O80.577 (3)0.6993 (10)1.1475 (5)4.5
N90.744 (2)0.6544 (4)0.8201 (3)4.5
C100.747 (2)0.3872 (4)1.1535 (4)4.5
H110.679 (4)0.5485 (16)1.1572 (12)5.4
H120.398 (3)0.8643 (17)1.0669 (14)5.4
H130.634 (3)0.913 (2)1.0690 (15)5.4
H140.567 (4)0.8874 (16)0.9592 (14)5.4
H150.750 (5)0.5719 (17)0.8303 (13)5.4
C160.766 (2)0.7065 (4)0.7267 (3)4.5
C170.8114 (19)0.2954 (4)1.1017 (4)4.5
C180.700 (2)0.3659 (4)1.2555 (4)4.5
C190.815 (2)0.6412 (4)0.6488 (3)4.5
C200.7335 (19)0.8254 (4)0.7061 (3)4.5
C210.8401 (18)0.1854 (4)1.1509 (3)4.5
H220.837 (4)0.3078 (16)1.0279 (15)5.4
C230.7358 (18)0.2568 (4)1.3049 (4)4.5
O240.6400 (14)0.4559 (6)1.3033 (4)4.5
C250.837 (2)0.6999 (4)0.5529 (3)4.5
C260.8430 (19)0.5215 (4)0.6615 (3)4.5
C270.755 (2)0.8834 (4)0.6104 (3)4.5
H280.699 (4)0.8716 (17)0.7625 (12)5.4
C290.8052 (17)0.1670 (4)1.2532 (3)4.5
N300.9011 (18)0.0952 (4)1.1029 (3)4.5
H310.715 (4)0.2430 (17)1.3790 (12)5.4
C320.6596 (8)0.4738 (4)1.3998 (4)4.5
C330.8074 (19)0.8177 (4)0.5342 (3)4.5
H340.875 (6)0.6570 (15)0.4946 (16)5.4
O350.831 (4)0.4625 (8)0.5953 (6)4.5
O360.8788 (16)0.4648 (5)0.7482 (5)4.5
C370.7094 (18)1.0008 (4)0.5907 (4)4.5
N380.8397 (17)0.0616 (4)1.3000 (3)4.5
C390.941 (2)0.0097 (4)1.1500 (4)4.5
H400.925 (4)0.1060 (15)1.0323 (15)5.4
H410.582 (4)0.4083 (16)1.4529 (14)5.4
H420.596 (4)0.558 (2)1.4118 (14)5.4
H430.815 (4)0.4719 (19)1.4077 (13)5.4
H440.824 (4)0.8550 (15)0.4635 (14)5.4
C450.9248 (8)0.3454 (4)0.7683 (4)4.5
O460.730 (4)1.0514 (10)0.5059 (6)4.5
O470.6300 (15)1.0623 (5)0.6617 (5)4.5
C480.9061 (18)0.0274 (4)1.2524 (3)4.5
H490.817 (4)0.0489 (17)1.3700 (13)5.4
O500.996 (5)0.0883 (7)1.1008 (6)4.5
H511.080 (4)0.3328 (17)0.7741 (13)5.4
H520.839 (4)0.3105 (15)0.8371 (12)5.4
H530.891 (4)0.301 (2)0.7105 (14)5.4
C540.5988 (8)1.1843 (4)0.6474 (4)4.5
O550.918 (4)0.1248 (7)1.3010 (7)4.5
H560.445 (3)1.2059 (15)0.6697 (13)5.4
H570.643 (5)1.2184 (15)0.5710 (12)5.4
H580.688 (4)1.2232 (17)0.6909 (14)5.4
Geometric parameters (Å, º) top
C1—C21.420 (8)C23—H311.02 (2)
C1—C31.425 (8)O24—C321.429 (8)
C1—N41.353 (7)C25—C331.394 (7)
C2—O51.27 (1)C25—H341.02 (2)
C2—N61.344 (6)C26—O351.25 (1)
C3—C71.491 (7)C26—O361.357 (9)
C3—O81.250 (9)C27—C331.406 (7)
N4—N91.294 (8)C27—C371.409 (8)
N6—C101.351 (8)C29—N381.354 (7)
N6—H110.96 (2)N30—C391.359 (9)
C7—H121.09 (2)N30—H400.97 (2)
C7—H131.09 (2)C32—H411.09 (2)
C7—H141.09 (2)C32—H421.10 (2)
N9—H150.97 (2)C32—H431.09 (3)
N9—C161.357 (6)C33—H441.02 (2)
C10—C171.412 (8)O36—C451.433 (7)
C10—C181.409 (7)C37—O461.246 (9)
C16—C191.418 (7)C37—O471.352 (9)
C16—C201.411 (7)N38—C481.354 (8)
C17—C211.406 (7)N38—H490.96 (2)
C17—H221.01 (2)C39—C481.408 (7)
C18—C231.407 (7)C39—O501.25 (1)
C18—O241.356 (9)C45—H511.09 (2)
C19—C251.414 (6)C45—H521.09 (2)
C19—C261.412 (7)C45—H531.09 (2)
C20—C271.409 (6)O47—C541.440 (7)
C20—H281.02 (2)C48—O551.26 (1)
C21—C291.408 (6)C54—H561.09 (2)
C21—N301.361 (8)C54—H571.09 (2)
C23—C291.398 (8)C54—H581.09 (2)
C2—C1—C3123.0 (4)C33—C25—H34117 (1)
C2—C1—N4121.0 (6)C19—C26—O35122.2 (7)
C3—C1—N4115.3 (5)C19—C26—O36120.6 (5)
C1—C2—O5121.1 (6)O35—C26—O36117.1 (7)
C1—C2—N6121.8 (6)C20—C27—C33117.4 (4)
O5—C2—N6116.8 (6)C20—C27—C37121.8 (5)
C1—C3—C7126.2 (5)C33—C27—C37120.6 (5)
C1—C3—O8119.9 (7)C21—C29—C23119.9 (5)
C7—C3—O8111.6 (8)C21—C29—N38119.0 (5)
C1—N4—N9128.1 (5)C23—C29—N38121.0 (4)
C2—N6—C10131.4 (6)C21—N30—C39122.4 (5)
C2—N6—H11113 (1)C21—N30—H40120 (1)
C10—N6—H11114 (1)C39—N30—H40118 (1)
C3—C7—H12109 (1)O24—C32—H41110 (1)
C3—C7—H13110 (1)O24—C32—H42108 (1)
C3—C7—H14114 (1)O24—C32—H43110 (1)
H12—C7—H13108 (1)H41—C32—H42109 (2)
H12—C7—H14108 (2)H41—C32—H43110 (2)
H13—C7—H14107 (2)H42—C32—H43109 (2)
N4—N9—H15117 (1)C25—C33—C27121.0 (4)
N4—N9—C16125.5 (5)C25—C33—H44118 (1)
H15—N9—C16117 (1)C27—C33—H44121 (1)
N6—C10—C17124.6 (5)C26—O36—C45126.0 (6)
N6—C10—C18116.1 (6)C27—C37—O46121.2 (7)
C17—C10—C18118.9 (4)C27—C37—O47121.9 (5)
N9—C16—C19120.2 (4)O46—C37—O47116.7 (8)
N9—C16—C20120.3 (5)C29—N38—C48122.6 (4)
C19—C16—C20119.4 (4)C29—N38—H49119 (1)
C10—C17—C21120.9 (4)C48—N38—H49118 (1)
C10—C17—H22120 (1)N30—C39—C48118.8 (6)
C21—C17—H22119 (1)N30—C39—O50118.6 (6)
C10—C18—C23120.0 (5)C48—C39—O50122.5 (6)
C10—C18—O24117.6 (5)O36—C45—H51110 (1)
C23—C18—O24122.1 (5)O36—C45—H52109 (1)
C16—C19—C25117.9 (5)O36—C45—H53110 (1)
C16—C19—C26123.8 (4)H51—C45—H52109 (2)
C25—C19—C26118.2 (4)H51—C45—H53109 (2)
C16—C20—C27122.4 (4)H52—C45—H53109 (2)
C16—C20—H28119 (1)C37—O47—C54124.2 (5)
C27—C20—H28119 (1)N38—C48—C39118.6 (5)
C17—C21—C29119.4 (5)N38—C48—O55118.6 (7)
C17—C21—N30122.2 (4)C39—C48—O55122.5 (6)
C29—C21—N30118.3 (4)O47—C54—H56110 (1)
C18—C23—C29120.5 (4)O47—C54—H57110 (1)
C18—C23—H31120 (1)O47—C54—H58109 (1)
C29—C23—H31119 (1)H56—C54—H57109 (2)
C18—O24—C32129.6 (6)H56—C54—H58109 (1)
C19—C25—C33121.8 (5)H57—C54—H58108 (2)
C19—C25—H34121 (1)

Experimental details

Crystal data
Chemical formulaC23H21N5O9
Mr511.45
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)6.9006 (3), 11.8347 (6), 14.0592 (7)
α, β, γ (°)81.811 (4), 81.032 (9), 87.541 (10)
V3)1122.31 (10)
Z2
Radiation typeSynchrotron, λ = 0.40007 Å
µ (mm1)0.03
Specimen shape, size (mm)Cylinder, 10 × 0.5
Data collection
DiffractometerHigh resolution
diffractometer (ID31, ESRF)
Specimen mounting?
Data collection modeTransmission
Scan methodContinuous
2θ values (°)2θmin = 1.300 2θmax = 18.750 2θstep = 0.005
Refinement
R factors and goodness of fitRp = 0.261, Rwp = 0.175, Rexp = 0.130, χ2 = 1.346
No. of data points5356
No. of parameters1375
No. of restraints159
H-atom treatmentH-atom parameters not refined

Computer programs: STOE WINXPOW (STOE & CIE GmbH, 2004), TOPAS (A.A.Coelho, 2007), DASH (W.I.F.David et al., 2006), Mercury (C.F. Macrae et al., 2008), DASH, TOPAS, Mercury.

 

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