Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803005324/ob6222sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803005324/ob6222Isup2.hkl |
CCDC reference: 209953
Key indicators
- Single-crystal X-ray study
- T = 93 K
- Mean (C-C) = 0.004 Å
- R factor = 0.042
- wR factor = 0.075
- Data-to-parameter ratio = 13.0
checkCIF results
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The title compound (I) was prepared according to the method described in the literature (Zambounis et al., 1996). Single crystals of (I) were grown from an acetonitrile solution.
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: TEXSAN; molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: TEXSAN.
Fig. 1. A view of the molecular structure of (I), showing ellipsoids at the 50% probability level for non-H atoms. |
C30H28N2O6 | F(000) = 540 |
Mr = 512.56 | Dx = 1.373 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.5418 Å |
a = 14.020 (2) Å | Cell parameters from 8483 reflections |
b = 6.5225 (8) Å | θ = 3.3–68.1° |
c = 14.153 (2) Å | µ = 0.79 mm−1 |
β = 106.704 (9)° | T = 93 K |
V = 1239.6 (3) Å3 | Hexagonal, colorless |
Z = 2 | 0.15 × 0.15 × 0.10 mm |
Rigaku R-AXIS RAPID Imaging Plate diffractometer | 1276 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.043 |
48 frames, delta ω = 15 deg scans | θmax = 68.1° |
Absorption correction: multi-scan (Higashi, 1995) | h = −16→16 |
Tmin = 0.791, Tmax = 0.924 | k = −7→7 |
10974 measured reflections | l = −17→16 |
2242 independent reflections |
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.042 | w = 1/[σ2(Fo2) + (0.015P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.075 | (Δ/σ)max = 0.001 |
S = 1.22 | Δρmax = 0.22 e Å−3 |
2240 reflections | Δρmin = −0.30 e Å−3 |
172 parameters |
C30H28N2O6 | V = 1239.6 (3) Å3 |
Mr = 512.56 | Z = 2 |
Monoclinic, P21/n | Cu Kα radiation |
a = 14.020 (2) Å | µ = 0.79 mm−1 |
b = 6.5225 (8) Å | T = 93 K |
c = 14.153 (2) Å | 0.15 × 0.15 × 0.10 mm |
β = 106.704 (9)° |
Rigaku R-AXIS RAPID Imaging Plate diffractometer | 2242 independent reflections |
Absorption correction: multi-scan (Higashi, 1995) | 1276 reflections with F2 > 2σ(F2) |
Tmin = 0.791, Tmax = 0.924 | Rint = 0.043 |
10974 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 172 parameters |
wR(F2) = 0.075 | H-atom parameters constrained |
S = 1.22 | Δρmax = 0.22 e Å−3 |
2240 reflections | Δρmin = −0.30 e Å−3 |
Refinement. Refinement using reflections with F2 > −10.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
O1 | 0.4729 (1) | 0.2002 (3) | 0.7325 (1) | 0.0310 (5) | |
O2 | 0.6930 (1) | 0.5357 (3) | 0.4293 (1) | 0.0311 (5) | |
O3 | 0.7469 (1) | 0.2143 (2) | 0.4809 (1) | 0.0248 (5) | |
N1 | 0.6229 (1) | 0.3498 (3) | 0.5324 (1) | 0.0226 (6) | |
C1 | 0.5124 (2) | 0.2518 (4) | 0.6691 (2) | 0.0248 (7) | |
C2 | 0.5692 (2) | 0.4438 (4) | 0.6753 (2) | 0.0232 (7) | |
C3 | 0.5717 (2) | 0.5818 (4) | 0.7523 (2) | 0.0272 (8) | |
C4 | 0.6264 (2) | 0.7592 (4) | 0.7642 (2) | 0.0281 (7) | |
C5 | 0.6807 (2) | 0.8019 (4) | 0.6975 (2) | 0.0272 (7) | |
C6 | 0.6798 (2) | 0.6708 (4) | 0.6210 (2) | 0.0258 (7) | |
C7 | 0.6224 (2) | 0.4897 (4) | 0.6082 (2) | 0.0240 (7) | |
C8 | 0.5619 (2) | 0.1732 (4) | 0.5160 (2) | 0.0228 (7) | |
C9 | 0.5527 (2) | 0.0484 (4) | 0.4339 (2) | 0.0246 (7) | |
C10 | 0.5076 (2) | 0.1237 (4) | 0.5820 (2) | 0.0211 (7) | |
C11 | 0.6905 (2) | 0.3809 (4) | 0.4740 (2) | 0.0266 (8) | |
C12 | 0.8130 (2) | 0.1908 (4) | 0.4146 (2) | 0.0276 (7) | |
C13 | 0.8959 (2) | 0.3490 (4) | 0.4427 (2) | 0.0362 (8) | |
C14 | 0.7512 (2) | 0.2046 (4) | 0.3082 (2) | 0.0314 (7) | |
C15 | 0.8531 (2) | −0.0251 (4) | 0.4405 (2) | 0.0333 (8) | |
H1 | 0.5347 | 0.5495 | 0.7988 | 0.0352* | |
H2 | 0.6274 | 0.8518 | 0.8172 | 0.0383* | |
H3 | 0.7214 | 0.9279 | 0.7051 | 0.0381* | |
H4 | 0.7186 | 0.7042 | 0.5754 | 0.0367* | |
H5 | 0.5909 | 0.0809 | 0.3877 | 0.0325* | |
H6 | 0.9329 | 0.3359 | 0.5094 | 0.0459* | |
H7 | 0.8658 | 0.4860 | 0.4339 | 0.0459* | |
H8 | 0.9378 | 0.3399 | 0.4013 | 0.0459* | |
H9 | 0.7179 | 0.3357 | 0.2947 | 0.0413* | |
H10 | 0.7913 | 0.1902 | 0.2639 | 0.0413* | |
H11 | 0.7006 | 0.1005 | 0.2919 | 0.0413* | |
H12 | 0.8964 | −0.0631 | 0.4020 | 0.0411* | |
H13 | 0.7992 | −0.1225 | 0.4270 | 0.0411* | |
H14 | 0.8890 | −0.0347 | 0.5085 | 0.0411* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.036 (1) | 0.035 (1) | 0.0247 (9) | −0.0042 (9) | 0.0127 (8) | −0.0023 (9) |
O2 | 0.034 (1) | 0.029 (1) | 0.0327 (10) | −0.0014 (9) | 0.0135 (8) | 0.0048 (9) |
O3 | 0.0224 (9) | 0.029 (1) | 0.0231 (9) | 0.0021 (9) | 0.0073 (7) | 0.0001 (8) |
N1 | 0.021 (1) | 0.026 (1) | 0.021 (1) | −0.001 (1) | 0.0079 (9) | −0.0022 (9) |
C1 | 0.021 (1) | 0.028 (2) | 0.022 (1) | 0.006 (1) | 0.001 (1) | 0.002 (1) |
C2 | 0.021 (1) | 0.026 (2) | 0.020 (1) | −0.001 (1) | 0.003 (1) | 0.000 (1) |
C3 | 0.025 (1) | 0.032 (2) | 0.022 (1) | 0.003 (1) | 0.004 (1) | 0.002 (1) |
C4 | 0.028 (1) | 0.031 (2) | 0.022 (1) | 0.000 (1) | 0.002 (1) | −0.005 (1) |
C5 | 0.023 (1) | 0.028 (2) | 0.025 (1) | 0.001 (1) | −0.002 (1) | 0.000 (1) |
C6 | 0.021 (1) | 0.030 (2) | 0.023 (1) | 0.002 (1) | 0.002 (1) | 0.002 (1) |
C7 | 0.023 (1) | 0.026 (2) | 0.020 (1) | 0.003 (1) | 0.001 (1) | −0.001 (1) |
C8 | 0.018 (1) | 0.024 (1) | 0.024 (1) | 0.003 (1) | 0.002 (1) | 0.002 (1) |
C9 | 0.019 (1) | 0.032 (2) | 0.022 (1) | 0.002 (1) | 0.004 (1) | 0.003 (1) |
C10 | 0.020 (1) | 0.025 (1) | 0.018 (1) | 0.003 (1) | 0.004 (1) | 0.000 (1) |
C11 | 0.024 (1) | 0.033 (2) | 0.020 (1) | −0.005 (1) | 0.002 (1) | −0.005 (1) |
C12 | 0.025 (1) | 0.034 (2) | 0.026 (1) | −0.004 (1) | 0.010 (1) | −0.003 (1) |
C13 | 0.029 (2) | 0.043 (2) | 0.039 (2) | −0.006 (1) | 0.013 (1) | −0.007 (1) |
C14 | 0.034 (1) | 0.034 (2) | 0.027 (1) | −0.001 (1) | 0.011 (1) | −0.001 (1) |
C15 | 0.032 (2) | 0.033 (2) | 0.035 (2) | 0.004 (1) | 0.010 (1) | 0.000 (1) |
O1—C1 | 1.229 (3) | C6—H4 | 0.981 |
O2—C11 | 1.198 (3) | C8—C9 | 1.393 (3) |
O3—C11 | 1.331 (3) | C8—C10 | 1.403 (3) |
O3—C12 | 1.504 (3) | C9—C10i | 1.384 (3) |
N1—C7 | 1.410 (3) | C9—H5 | 0.980 |
N1—C8 | 1.413 (3) | C12—C13 | 1.520 (3) |
N1—C11 | 1.439 (3) | C12—C14 | 1.509 (3) |
C1—C2 | 1.474 (3) | C12—C15 | 1.522 (3) |
C1—C10 | 1.474 (3) | C13—H6 | 0.940 |
C2—C3 | 1.406 (3) | C13—H7 | 0.981 |
C2—C7 | 1.398 (3) | C13—H8 | 0.944 |
C3—C4 | 1.371 (3) | C14—H9 | 0.966 |
C3—H1 | 0.972 | C14—H10 | 0.960 |
C4—C5 | 1.401 (3) | C14—H11 | 0.961 |
C4—H2 | 0.960 | C15—H12 | 0.958 |
C5—C6 | 1.377 (3) | C15—H13 | 0.963 |
C5—H3 | 0.989 | C15—H14 | 0.951 |
C6—C7 | 1.411 (3) | ||
O1···O2ii | 3.249 (2) | C4···C10vi | 3.551 (3) |
O1···C13iii | 3.460 (3) | C5···C10vi | 3.269 (3) |
O1···C4iv | 3.543 (3) | C5···C9ii | 3.409 (3) |
O2···C1ii | 3.138 (3) | C5···C7vii | 3.510 (3) |
O2···C2ii | 3.550 (3) | C5···C8vi | 3.575 (3) |
O2···C10ii | 3.552 (3) | C6···C8ii | 3.535 (3) |
O3···C4v | 3.545 (3) | C6···C10ii | 3.551 (3) |
N1···C7ii | 3.598 (3) | C7···C8ii | 3.462 (3) |
C2···C5v | 3.572 (3) | C13···C13viii | 3.509 (5) |
C4···C9ii | 3.420 (3) | ||
C11—O3—C12 | 119.8 (2) | C1—C10—C8 | 121.5 (2) |
C7—N1—C8 | 121.2 (2) | C1—C10—C9i | 118.4 (2) |
C7—N1—C11 | 119.6 (2) | C8—C10—C9i | 120.1 (2) |
C8—N1—C11 | 119.2 (2) | O2—C11—O3 | 128.3 (2) |
O1—C1—C2 | 122.6 (2) | O2—C11—N1 | 123.2 (2) |
O1—C1—C10 | 122.2 (2) | O3—C11—N1 | 108.5 (2) |
C2—C1—C10 | 115.2 (2) | O3—C12—C13 | 109.2 (2) |
C1—C2—C3 | 118.9 (2) | O3—C12—C14 | 109.7 (2) |
C1—C2—C7 | 121.8 (2) | O3—C12—C15 | 101.3 (2) |
C3—C2—C7 | 119.4 (2) | C13—C12—C14 | 113.4 (2) |
C2—C3—C4 | 121.6 (2) | C13—C12—C15 | 111.3 (2) |
C2—C3—H1 | 119.1 | C14—C12—C15 | 111.2 (2) |
C4—C3—H1 | 119.3 | C12—C13—H6 | 111.2 |
C3—C4—C5 | 118.5 (2) | C12—C13—H7 | 108.5 |
C3—C4—H2 | 120.6 | C12—C13—H8 | 111.1 |
C5—C4—H2 | 120.8 | H6—C13—H7 | 107.7 |
C4—C5—C6 | 121.5 (2) | H6—C13—H8 | 110.8 |
C4—C5—H3 | 120.1 | H7—C13—H8 | 107.4 |
C6—C5—H3 | 118.5 | C12—C14—H9 | 110.9 |
C5—C6—C7 | 119.8 (2) | C12—C14—H10 | 111.7 |
C5—C6—H4 | 119.8 | C12—C14—H11 | 111.7 |
C7—C6—H4 | 120.3 | H9—C14—H10 | 107.3 |
N1—C7—C2 | 119.9 (2) | H9—C14—H11 | 107.2 |
N1—C7—C6 | 120.8 (2) | H10—C14—H11 | 107.8 |
C2—C7—C6 | 119.2 (2) | C12—C15—H12 | 110.7 |
N1—C8—C9 | 121.3 (2) | C12—C15—H13 | 110.4 |
N1—C8—C10 | 119.8 (2) | C12—C15—H14 | 110.8 |
C9—C8—C10 | 118.9 (2) | H12—C15—H13 | 107.8 |
C8—C9—C10i | 121.0 (2) | H12—C15—H14 | 108.8 |
C8—C9—H5 | 119.5 | H13—C15—H14 | 108.3 |
C10i—C9—H5 | 119.5 | ||
O1—C1—C2—C3 | −5.4 (3) | C2—C1—C10—C9i | −173.6 (2) |
O1—C1—C2—C7 | 173.1 (2) | C2—C3—C4—C5 | 0.0 (4) |
O1—C1—C10—C8 | −172.9 (2) | C2—C7—N1—C8 | 6.9 (3) |
O1—C1—C10—C9i | 7.4 (3) | C2—C7—N1—C11 | −169.6 (2) |
O2—C11—O3—C12 | −10.8 (4) | C2—C7—C6—C5 | −1.6 (3) |
O2—C11—N1—C7 | −56.1 (3) | C3—C2—C1—C10 | 175.6 (2) |
O2—C11—N1—C8 | 127.2 (2) | C3—C2—C7—C6 | 1.9 (3) |
O3—C11—N1—C7 | 122.9 (2) | C3—C4—C5—C6 | 0.2 (4) |
O3—C11—N1—C8 | −53.7 (3) | C4—C3—C2—C7 | −1.1 (3) |
N1—C7—C2—C1 | −0.3 (3) | C4—C5—C6—C7 | 0.6 (4) |
N1—C7—C2—C3 | 178.2 (2) | C6—C7—N1—C8 | −176.9 (2) |
N1—C7—C6—C5 | −177.9 (2) | C6—C7—N1—C11 | 6.6 (3) |
N1—C8—C9—C10i | −179.6 (2) | C7—N1—C8—C9 | 171.9 (2) |
N1—C8—C10—C1 | −0.1 (3) | C7—N1—C8—C10 | −6.7 (3) |
N1—C8—C10—C9i | 179.6 (2) | C7—C2—C1—C10 | −5.9 (3) |
N1—C11—O3—C12 | 170.3 (2) | C9—C8—N1—C11 | −11.5 (3) |
C1—C2—C3—C4 | 177.5 (2) | C10—C8—N1—C11 | 169.9 (2) |
C1—C2—C7—C6 | −176.6 (2) | C11—O3—C12—C13 | 68.2 (2) |
C1—C10—C8—C9 | −178.7 (2) | C11—O3—C12—C14 | −56.7 (3) |
C1—C10—C9i—C8i | 178.7 (2) | C11—O3—C12—C15 | −174.3 (2) |
C2—C1—C10—C8 | 6.1 (3) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x−1/2, −y+1/2, z+1/2; (iv) x, y−1, z; (v) −x+3/2, y−1/2, −z+3/2; (vi) x, y+1, z; (vii) −x+3/2, y+1/2, −z+3/2; (viii) −x+2, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C30H28N2O6 |
Mr | 512.56 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 93 |
a, b, c (Å) | 14.020 (2), 6.5225 (8), 14.153 (2) |
β (°) | 106.704 (9) |
V (Å3) | 1239.6 (3) |
Z | 2 |
Radiation type | Cu Kα |
µ (mm−1) | 0.79 |
Crystal size (mm) | 0.15 × 0.15 × 0.10 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID Imaging Plate diffractometer |
Absorption correction | Multi-scan (Higashi, 1995) |
Tmin, Tmax | 0.791, 0.924 |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 10974, 2242, 1276 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.075, 1.22 |
No. of reflections | 2240 |
No. of parameters | 172 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.30 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), PROCESS-AUTO, TEXSAN (Molecular Structure Corporation, 2001), SHELXS86 (Sheldrick, 1985), TEXSAN, ORTEPIII (Burnett & Johnson, 1996).
O1—C1 | 1.229 (3) | C2—C3 | 1.406 (3) |
O2—C11 | 1.198 (3) | C2—C7 | 1.398 (3) |
O3—C11 | 1.331 (3) | C3—C4 | 1.371 (3) |
O3—C12 | 1.504 (3) | C4—C5 | 1.401 (3) |
N1—C7 | 1.410 (3) | C5—C6 | 1.377 (3) |
N1—C8 | 1.413 (3) | C6—C7 | 1.411 (3) |
N1—C11 | 1.439 (3) | C8—C9 | 1.393 (3) |
C1—C2 | 1.474 (3) | C8—C10 | 1.403 (3) |
C1—C10 | 1.474 (3) | C9—C10i | 1.384 (3) |
O2—C11—N1—C7 | −56.1 (3) | N1—C7—C2—C3 | 178.2 (2) |
O2—C11—N1—C8 | 127.2 (2) | C1—C2—C7—C6 | −176.6 (2) |
O3—C11—N1—C7 | 122.9 (2) | C1—C10—C8—C9 | −178.7 (2) |
O3—C11—N1—C8 | −53.7 (3) |
Symmetry code: (i) −x+1, −y, −z+1. |
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The title compound, (I), is a soluble yellow precursor (`latent pigment') (Zambounis et al., 1996, 1997) of quinacridone pigments (QA) (Herbst & Hunger, 1997) that are known as industrially important red pigments. The soluble precursor is prepared by replacing the H atom of the NH group with a tert-butoxycarbonyl (t-BOC) group, hereafter called t-BOC QA. The insoluble parent QA can then be regenerated by thermochemical treatment of the precursor. The present `latent pigment technology' is a versatile and promising technique for the preparation of nano pigment particles, as well as transparent pigmented thin films, etc. The crystal structure of the parent QA has previously been reported by Potts et al. (1994) and by us (Mizuguchi et al., 2002). The present paper describes the crystal structure of t-BOC QA, (I).
The title compound crystallizes in space group P21/n and the molecule belongs to the molecular symmetry of Ci (Fig. 1). The t-BOC groups attached to the N atom of the acridine skeleton are symmetrically twisted to the heterocyclic ring by 55.57 (8)° (N1/C11/O2/O3 and N1/C1/C2/C7/C8/C10). The condensed ring system is not entirely planar. The dihedral angles between two condensed rings are 174.56 (6)° [N1/C1/C2/C7/C8/C10 and C8–C10/C8i–C10i; symmetry code: (i) 1 − x, −y, 1 − z] and 179.11 (8)° (N1/C1/C2/C7/C8/C10 and C2–C7). The molecules are stacked along the a axis.