Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807013189/sj2257sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807013189/sj2257Isup2.hkl |
CCDC reference: 643659
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.001 Å
- R factor = 0.044
- wR factor = 0.127
- Data-to-parameter ratio = 23.0
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.725 0.978 Tmin(prime) and Tmax expected: 0.949 0.977 RR(prime) = 0.763 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.76 PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) . 10 Ang. PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 6 PLAT333_ALERT_2_C Large Average Benzene C-C Dist. C11 -C20 1.45 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 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
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); 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).
C23H15NO4 | Z = 2 |
Mr = 369.36 | F(000) = 384 |
Triclinic, P1 | Dx = 1.503 Mg m−3 |
Hall symbol: -P 1 | Melting point = 511–513 K |
a = 7.0913 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.5435 (1) Å | Cell parameters from 7314 reflections |
c = 11.2808 (1) Å | θ = 2.0–32.5° |
α = 79.550 (1)° | µ = 0.10 mm−1 |
β = 86.680 (1)° | T = 100 K |
γ = 79.737 (1)° | Block, yellow |
V = 815.89 (2) Å3 | 0.49 × 0.35 × 0.22 mm |
Bruker SMART APEXII CCD area-detector diffractometer | 5861 independent reflections |
Radiation source: fine-focus sealed tube | 5199 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
Detector resolution: 8.33 pixels mm-1 | θmax = 32.5°, θmin = 2.0° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −15→15 |
Tmin = 0.725, Tmax = 0.978 | l = −16→17 |
11945 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)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.0751P)2 + 0.2183P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
5861 reflections | Δρmax = 0.54 e Å−3 |
255 parameters | Δρmin = −0.29 e Å−3 |
0 restraints | Extinction correction: SHELXTL (Sheldrick, 1998), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.088 (7) |
Experimental. The data were collected using 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 | ||
O1 | 0.41352 (9) | 0.75927 (6) | −0.24460 (6) | 0.01458 (13) | |
O2 | 0.09286 (10) | 0.79122 (7) | −0.25816 (6) | 0.01638 (14) | |
O3 | 0.17552 (11) | 0.43053 (7) | 0.29997 (6) | 0.01881 (15) | |
O4 | 0.19806 (11) | 0.89083 (6) | −0.00694 (6) | 0.01698 (14) | |
N1 | 0.24201 (10) | 0.44546 (7) | 0.03308 (6) | 0.01065 (13) | |
C1 | 0.24795 (12) | 0.31201 (8) | 0.07331 (8) | 0.01235 (15) | |
H1A | 0.2247 | 0.2803 | 0.1543 | 0.015* | |
C2 | 0.28782 (13) | 0.22918 (8) | −0.00662 (8) | 0.01381 (15) | |
H2A | 0.2932 | 0.1399 | 0.0204 | 0.017* | |
C3 | 0.32215 (12) | 0.27594 (8) | −0.13241 (8) | 0.01245 (15) | |
C4 | 0.36546 (13) | 0.18835 (9) | −0.21475 (8) | 0.01560 (16) | |
H4A | 0.3752 | 0.0988 | −0.1874 | 0.019* | |
C5 | 0.39345 (14) | 0.23508 (9) | −0.33595 (8) | 0.01672 (17) | |
H5A | 0.4221 | 0.1767 | −0.3898 | 0.020* | |
C6 | 0.37890 (14) | 0.37010 (9) | −0.37836 (8) | 0.01609 (17) | |
H6A | 0.3971 | 0.4007 | −0.4601 | 0.019* | |
C7 | 0.33762 (13) | 0.45779 (8) | −0.29914 (8) | 0.01424 (16) | |
H7A | 0.3285 | 0.5471 | −0.3278 | 0.017* | |
C8 | 0.30928 (12) | 0.41209 (8) | −0.17480 (7) | 0.01149 (15) | |
C9 | 0.26685 (12) | 0.49918 (8) | −0.08825 (7) | 0.01083 (15) | |
C10 | 0.24443 (12) | 0.63503 (8) | −0.09672 (7) | 0.01086 (14) | |
C11 | 0.20917 (12) | 0.66228 (8) | 0.02069 (7) | 0.01111 (14) | |
C12 | 0.18228 (12) | 0.78886 (8) | 0.06206 (7) | 0.01185 (15) | |
C13 | 0.13789 (12) | 0.78356 (8) | 0.19364 (7) | 0.01181 (15) | |
C14 | 0.09389 (13) | 0.90051 (8) | 0.23892 (8) | 0.01376 (15) | |
H14A | 0.0899 | 0.9801 | 0.1869 | 0.017* | |
C15 | 0.05599 (13) | 0.89813 (9) | 0.36174 (8) | 0.01474 (16) | |
H15A | 0.0270 | 0.9763 | 0.3914 | 0.018* | |
C16 | 0.06134 (13) | 0.77918 (9) | 0.44050 (8) | 0.01467 (16) | |
H16A | 0.0381 | 0.7779 | 0.5227 | 0.018* | |
C17 | 0.10168 (13) | 0.66215 (9) | 0.39566 (8) | 0.01370 (15) | |
H17A | 0.1035 | 0.5829 | 0.4480 | 0.016* | |
C18 | 0.13925 (12) | 0.66312 (8) | 0.27281 (7) | 0.01180 (15) | |
C19 | 0.17588 (12) | 0.53431 (8) | 0.22967 (7) | 0.01221 (15) | |
C20 | 0.20749 (12) | 0.54474 (8) | 0.10029 (7) | 0.01105 (14) | |
C21 | 0.23822 (12) | 0.73651 (8) | −0.20768 (7) | 0.01118 (15) | |
C22 | 0.42074 (13) | 0.86031 (9) | −0.35030 (8) | 0.01533 (16) | |
H22A | 0.3328 | 0.9395 | −0.3398 | 0.018* | |
H22B | 0.3855 | 0.8310 | −0.4214 | 0.018* | |
C23 | 0.62385 (13) | 0.88583 (9) | −0.36364 (9) | 0.01744 (17) | |
H23A | 0.6368 | 0.9489 | −0.4352 | 0.026* | |
H23B | 0.7098 | 0.8057 | −0.3695 | 0.026* | |
H23C | 0.6545 | 0.9191 | −0.2947 | 0.026* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0128 (3) | 0.0154 (3) | 0.0137 (3) | −0.0035 (2) | 0.0003 (2) | 0.0032 (2) |
O2 | 0.0141 (3) | 0.0184 (3) | 0.0149 (3) | −0.0029 (2) | −0.0013 (2) | 0.0021 (2) |
O3 | 0.0296 (4) | 0.0126 (3) | 0.0124 (3) | −0.0020 (3) | 0.0017 (3) | 0.0004 (2) |
O4 | 0.0246 (3) | 0.0114 (3) | 0.0144 (3) | −0.0039 (2) | 0.0013 (2) | −0.0005 (2) |
N1 | 0.0123 (3) | 0.0099 (3) | 0.0097 (3) | −0.0021 (2) | 0.0000 (2) | −0.0016 (2) |
C1 | 0.0139 (3) | 0.0099 (3) | 0.0126 (3) | −0.0017 (3) | −0.0008 (3) | −0.0004 (3) |
C2 | 0.0159 (4) | 0.0111 (3) | 0.0140 (3) | −0.0019 (3) | −0.0006 (3) | −0.0014 (3) |
C3 | 0.0124 (3) | 0.0118 (3) | 0.0133 (3) | −0.0016 (3) | −0.0008 (3) | −0.0027 (3) |
C4 | 0.0173 (4) | 0.0136 (3) | 0.0165 (4) | −0.0018 (3) | −0.0003 (3) | −0.0052 (3) |
C5 | 0.0183 (4) | 0.0163 (4) | 0.0169 (4) | −0.0023 (3) | 0.0008 (3) | −0.0073 (3) |
C6 | 0.0181 (4) | 0.0177 (4) | 0.0132 (3) | −0.0031 (3) | 0.0014 (3) | −0.0051 (3) |
C7 | 0.0174 (4) | 0.0136 (3) | 0.0120 (3) | −0.0033 (3) | 0.0008 (3) | −0.0029 (3) |
C8 | 0.0114 (3) | 0.0121 (3) | 0.0112 (3) | −0.0020 (3) | 0.0001 (3) | −0.0028 (3) |
C9 | 0.0119 (3) | 0.0111 (3) | 0.0092 (3) | −0.0022 (3) | 0.0003 (2) | −0.0010 (2) |
C10 | 0.0125 (3) | 0.0104 (3) | 0.0095 (3) | −0.0025 (3) | 0.0006 (3) | −0.0011 (2) |
C11 | 0.0121 (3) | 0.0105 (3) | 0.0105 (3) | −0.0022 (3) | 0.0002 (3) | −0.0012 (2) |
C12 | 0.0128 (3) | 0.0113 (3) | 0.0115 (3) | −0.0021 (3) | −0.0005 (3) | −0.0022 (3) |
C13 | 0.0120 (3) | 0.0125 (3) | 0.0113 (3) | −0.0025 (3) | 0.0000 (3) | −0.0028 (3) |
C14 | 0.0152 (4) | 0.0133 (3) | 0.0137 (3) | −0.0030 (3) | 0.0001 (3) | −0.0043 (3) |
C15 | 0.0150 (4) | 0.0162 (4) | 0.0145 (4) | −0.0028 (3) | 0.0002 (3) | −0.0067 (3) |
C16 | 0.0141 (4) | 0.0185 (4) | 0.0123 (3) | −0.0029 (3) | 0.0002 (3) | −0.0052 (3) |
C17 | 0.0146 (3) | 0.0155 (4) | 0.0108 (3) | −0.0024 (3) | −0.0003 (3) | −0.0021 (3) |
C18 | 0.0120 (3) | 0.0122 (3) | 0.0112 (3) | −0.0020 (3) | −0.0001 (3) | −0.0023 (3) |
C19 | 0.0131 (3) | 0.0125 (3) | 0.0106 (3) | −0.0014 (3) | −0.0001 (3) | −0.0018 (3) |
C20 | 0.0125 (3) | 0.0108 (3) | 0.0099 (3) | −0.0020 (3) | 0.0001 (3) | −0.0021 (2) |
C21 | 0.0134 (3) | 0.0106 (3) | 0.0100 (3) | −0.0030 (3) | 0.0011 (3) | −0.0024 (2) |
C22 | 0.0153 (4) | 0.0163 (4) | 0.0130 (3) | −0.0050 (3) | −0.0006 (3) | 0.0036 (3) |
C23 | 0.0152 (4) | 0.0178 (4) | 0.0179 (4) | −0.0053 (3) | −0.0003 (3) | 0.0031 (3) |
O1—C21 | 1.3366 (10) | C10—C11 | 1.4048 (11) |
O1—C22 | 1.4529 (10) | C10—C21 | 1.4891 (11) |
O2—C21 | 1.2068 (11) | C11—C20 | 1.3938 (11) |
O3—C19 | 1.2297 (10) | C11—C12 | 1.4698 (11) |
O4—C12 | 1.2262 (10) | C12—C13 | 1.4924 (12) |
N1—C20 | 1.3805 (10) | C13—C14 | 1.3969 (12) |
N1—C1 | 1.3918 (10) | C13—C18 | 1.4127 (11) |
N1—C9 | 1.3969 (10) | C14—C15 | 1.3926 (12) |
C1—C2 | 1.3504 (12) | C14—H14A | 0.9300 |
C1—H1A | 0.9300 | C15—C16 | 1.3952 (13) |
C2—C3 | 1.4370 (12) | C15—H15A | 0.9300 |
C2—H2A | 0.9300 | C16—C17 | 1.3943 (12) |
C3—C4 | 1.4096 (12) | C16—H16A | 0.9300 |
C3—C8 | 1.4167 (12) | C17—C18 | 1.3945 (11) |
C4—C5 | 1.3821 (13) | C17—H17A | 0.9300 |
C4—H4A | 0.9300 | C18—C19 | 1.4993 (12) |
C5—C6 | 1.4045 (13) | C19—C20 | 1.4509 (11) |
C5—H5A | 0.9300 | C22—C23 | 1.5059 (13) |
C6—C7 | 1.3828 (12) | C22—H22A | 0.9700 |
C6—H6A | 0.9300 | C22—H22B | 0.9700 |
C7—C8 | 1.4130 (11) | C23—H23A | 0.9600 |
C7—H7A | 0.9300 | C23—H23B | 0.9600 |
C8—C9 | 1.4421 (11) | C23—H23C | 0.9600 |
C9—C10 | 1.3989 (11) | ||
C21—O1—C22 | 115.45 (7) | C14—C13—C18 | 119.56 (8) |
C20—N1—C1 | 127.96 (7) | C14—C13—C12 | 119.04 (7) |
C20—N1—C9 | 109.22 (7) | C18—C13—C12 | 121.39 (7) |
C1—N1—C9 | 122.81 (7) | C15—C14—C13 | 120.17 (8) |
C2—C1—N1 | 119.22 (8) | C15—C14—H14A | 119.9 |
C2—C1—H1A | 120.4 | C13—C14—H14A | 119.9 |
N1—C1—H1A | 120.4 | C14—C15—C16 | 120.36 (8) |
C1—C2—C3 | 121.46 (8) | C14—C15—H15A | 119.8 |
C1—C2—H2A | 119.3 | C16—C15—H15A | 119.8 |
C3—C2—H2A | 119.3 | C17—C16—C15 | 119.79 (8) |
C4—C3—C8 | 119.43 (8) | C17—C16—H16A | 120.1 |
C4—C3—C2 | 120.92 (8) | C15—C16—H16A | 120.1 |
C8—C3—C2 | 119.64 (8) | C16—C17—C18 | 120.44 (8) |
C5—C4—C3 | 120.24 (8) | C16—C17—H17A | 119.8 |
C5—C4—H4A | 119.9 | C18—C17—H17A | 119.8 |
C3—C4—H4A | 119.9 | C17—C18—C13 | 119.65 (8) |
C4—C5—C6 | 120.43 (8) | C17—C18—C19 | 117.89 (7) |
C4—C5—H5A | 119.8 | C13—C18—C19 | 122.45 (7) |
C6—C5—H5A | 119.8 | O3—C19—C20 | 124.32 (8) |
C7—C6—C5 | 120.33 (8) | O3—C19—C18 | 121.47 (8) |
C7—C6—H6A | 119.8 | C20—C19—C18 | 114.20 (7) |
C5—C6—H6A | 119.8 | N1—C20—C11 | 107.38 (7) |
C6—C7—C8 | 120.17 (8) | N1—C20—C19 | 128.28 (7) |
C6—C7—H7A | 119.9 | C11—C20—C19 | 124.34 (7) |
C8—C7—H7A | 119.9 | O2—C21—O1 | 124.20 (8) |
C7—C8—C3 | 119.39 (8) | O2—C21—C10 | 124.16 (8) |
C7—C8—C9 | 122.44 (8) | O1—C21—C10 | 111.64 (7) |
C3—C8—C9 | 118.17 (7) | O1—C22—C23 | 106.69 (7) |
N1—C9—C10 | 107.55 (7) | O1—C22—H22A | 110.4 |
N1—C9—C8 | 118.61 (7) | C23—C22—H22A | 110.4 |
C10—C9—C8 | 133.84 (7) | O1—C22—H22B | 110.4 |
C9—C10—C11 | 107.20 (7) | C23—C22—H22B | 110.4 |
C9—C10—C21 | 128.11 (7) | H22A—C22—H22B | 108.6 |
C11—C10—C21 | 124.43 (7) | C22—C23—H23A | 109.5 |
C20—C11—C10 | 108.65 (7) | C22—C23—H23B | 109.5 |
C20—C11—C12 | 122.18 (7) | H23A—C23—H23B | 109.5 |
C10—C11—C12 | 129.15 (7) | C22—C23—H23C | 109.5 |
O4—C12—C11 | 121.98 (8) | H23A—C23—H23C | 109.5 |
O4—C12—C13 | 122.78 (8) | H23B—C23—H23C | 109.5 |
C11—C12—C13 | 115.23 (7) | ||
C20—N1—C1—C2 | −178.75 (8) | C11—C12—C13—C14 | −174.54 (7) |
C9—N1—C1—C2 | 3.07 (12) | O4—C12—C13—C18 | −173.67 (8) |
N1—C1—C2—C3 | −0.69 (13) | C11—C12—C13—C18 | 5.37 (12) |
C1—C2—C3—C4 | 179.38 (8) | C18—C13—C14—C15 | 1.48 (13) |
C1—C2—C3—C8 | −1.66 (13) | C12—C13—C14—C15 | −178.62 (8) |
C8—C3—C4—C5 | −0.56 (13) | C13—C14—C15—C16 | −0.09 (13) |
C2—C3—C4—C5 | 178.39 (8) | C14—C15—C16—C17 | −1.08 (13) |
C3—C4—C5—C6 | −0.06 (14) | C15—C16—C17—C18 | 0.86 (13) |
C4—C5—C6—C7 | 0.43 (14) | C16—C17—C18—C13 | 0.53 (13) |
C5—C6—C7—C8 | −0.15 (14) | C16—C17—C18—C19 | −178.22 (8) |
C6—C7—C8—C3 | −0.47 (13) | C14—C13—C18—C17 | −1.69 (12) |
C6—C7—C8—C9 | 179.69 (8) | C12—C13—C18—C17 | 178.40 (8) |
C4—C3—C8—C7 | 0.82 (12) | C14—C13—C18—C19 | 177.00 (8) |
C2—C3—C8—C7 | −178.15 (8) | C12—C13—C18—C19 | −2.91 (12) |
C4—C3—C8—C9 | −179.33 (7) | C17—C18—C19—O3 | −0.92 (13) |
C2—C3—C8—C9 | 1.70 (12) | C13—C18—C19—O3 | −179.63 (8) |
C20—N1—C9—C10 | −0.88 (9) | C17—C18—C19—C20 | 178.10 (7) |
C1—N1—C9—C10 | 177.61 (7) | C13—C18—C19—C20 | −0.61 (12) |
C20—N1—C9—C8 | 178.56 (7) | C1—N1—C20—C11 | −177.96 (8) |
C1—N1—C9—C8 | −2.96 (12) | C9—N1—C20—C11 | 0.42 (9) |
C7—C8—C9—N1 | −179.65 (7) | C1—N1—C20—C19 | 2.47 (14) |
C3—C8—C9—N1 | 0.50 (12) | C9—N1—C20—C19 | −179.15 (8) |
C7—C8—C9—C10 | −0.39 (15) | C10—C11—C20—N1 | 0.20 (9) |
C3—C8—C9—C10 | 179.76 (9) | C12—C11—C20—N1 | −178.30 (7) |
N1—C9—C10—C11 | 0.98 (9) | C10—C11—C20—C19 | 179.79 (8) |
C8—C9—C10—C11 | −178.34 (9) | C12—C11—C20—C19 | 1.29 (13) |
N1—C9—C10—C21 | −173.34 (8) | O3—C19—C20—N1 | −0.05 (15) |
C8—C9—C10—C21 | 7.34 (15) | C18—C19—C20—N1 | −179.05 (8) |
C9—C10—C11—C20 | −0.74 (9) | O3—C19—C20—C11 | −179.56 (8) |
C21—C10—C11—C20 | 173.85 (7) | C18—C19—C20—C11 | 1.45 (12) |
C9—C10—C11—C12 | 177.62 (8) | C22—O1—C21—O2 | 2.12 (12) |
C21—C10—C11—C12 | −7.79 (14) | C22—O1—C21—C10 | −178.03 (7) |
C20—C11—C12—O4 | 174.44 (8) | C9—C10—C21—O2 | 91.73 (11) |
C10—C11—C12—O4 | −3.72 (14) | C11—C10—C21—O2 | −81.69 (11) |
C20—C11—C12—C13 | −4.61 (12) | C9—C10—C21—O1 | −88.12 (10) |
C10—C11—C12—C13 | 177.23 (8) | C11—C10—C21—O1 | 98.46 (9) |
O4—C12—C13—C14 | 6.42 (13) | C21—O1—C22—C23 | 170.70 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O3 | 0.93 | 2.45 | 3.024 (1) | 120 |
C16—H16A···O2i | 0.93 | 2.56 | 3.446 (1) | 160 |
C23—H23B···O3ii | 0.96 | 2.47 | 3.350 (1) | 152 |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, −y+1, −z. |
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