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In the title compound, C
17H
13NO
2, the hydroxamate group adopts a
trans conformation. The crystal packing is stabilized by intermolecular O—H
O hydrogen bonds and C—H
π interactions.
Supporting information
CCDC reference: 642919
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean (C-C) = 0.002 Å
- R factor = 0.051
- wR factor = 0.121
- Data-to-parameter ratio = 14.5
checkCIF/PLATON results
No syntax errors found
Alert level C
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 27.48
From the CIF: _diffrn_reflns_theta_full 27.50
From the CIF: _reflns_number_total 2692
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 2857
Completeness (_total/calc) 94.22%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.94
PLAT028_ALERT_3_C _diffrn_measured_fraction_theta_max Low ....... 0.94
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.21 Ratio
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 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
4 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2006); program(s) used to solve structure: SIR2002 (Burla et al., 2002); program(s) used to refine structure: SHELXL97 (Sheldrick 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Version 1.3; Bruno et
al., 2002); software used to prepare material for publication: CrystalStructure.
N-Hydroxy-
N-phenylnaphthalene-2-carboxamide
top
Crystal data top
C17H13NO2 | F(000) = 552.00 |
Mr = 263.30 | Dx = 1.405 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: -P 2ybc | Cell parameters from 2692 reflections |
a = 27.643 (15) Å | θ = 3.1–27.5° |
b = 5.638 (3) Å | µ = 0.09 mm−1 |
c = 8.018 (4) Å | T = 123 K |
β = 95.1601 (18)° | Prism, silver |
V = 1244.6 (11) Å3 | 0.20 × 0.15 × 0.10 mm |
Z = 4 | |
Data collection top
Rigaku Saturn CCD diffractometer | Rint = 0.048 |
ω scans | θmax = 27.5°, θmin = 4.2° |
11623 measured reflections | h = −35→35 |
2692 independent reflections | k = −7→6 |
2423 reflections with I > 2σ(I) | l = −10→7 |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.051 | w = 1/[σ2(Fo2) + (0.0447P)2 + 0.6927P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.121 | (Δ/σ)max < 0.001 |
S = 1.13 | Δρmax = 0.28 e Å−3 |
2692 reflections | Δρmin = −0.23 e Å−3 |
186 parameters | |
Special details top
Refinement. Refinement was performed using all reflections. 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). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.70302 (4) | 0.2416 (2) | 0.10352 (16) | 0.0223 (2) | |
O2 | 0.72152 (4) | 0.8111 (2) | −0.04283 (17) | 0.0267 (3) | |
N1 | 0.69303 (5) | 0.4406 (2) | 0.00038 (17) | 0.0179 (3) | |
C1 | 0.64310 (6) | 0.4731 (2) | −0.0571 (2) | 0.0171 (3) | |
C2 | 0.60908 (6) | 0.3149 (2) | −0.0036 (2) | 0.0206 (3) | |
C3 | 0.56045 (6) | 0.3380 (3) | −0.0632 (2) | 0.0245 (3) | |
C4 | 0.54540 (6) | 0.5166 (3) | −0.1743 (2) | 0.0243 (3) | |
C5 | 0.57958 (6) | 0.6729 (3) | −0.2276 (2) | 0.0234 (3) | |
C6 | 0.62841 (6) | 0.6523 (2) | −0.1709 (2) | 0.0211 (3) | |
C7 | 0.72925 (6) | 0.6046 (2) | 0.0020 (2) | 0.0179 (3) | |
C8 | 0.80907 (5) | 0.6742 (2) | 0.15485 (19) | 0.0155 (3) | |
C9 | 0.77979 (6) | 0.5226 (2) | 0.0568 (2) | 0.0162 (3) | |
C10 | 0.79874 (6) | 0.3050 (2) | 0.0010 (2) | 0.0168 (3) | |
C11 | 0.84592 (6) | 0.2435 (2) | 0.04807 (19) | 0.0155 (3) | |
C12 | 0.87658 (6) | 0.3946 (2) | 0.15196 (19) | 0.0148 (3) | |
C13 | 0.92557 (6) | 0.3349 (2) | 0.2030 (2) | 0.0174 (3) | |
C14 | 0.95426 (6) | 0.4847 (2) | 0.3033 (2) | 0.0195 (3) | |
C15 | 0.93555 (6) | 0.7027 (2) | 0.3568 (2) | 0.0192 (3) | |
C16 | 0.88868 (6) | 0.7662 (2) | 0.3081 (2) | 0.0169 (3) | |
C17 | 0.85793 (5) | 0.6139 (2) | 0.20544 (19) | 0.0146 (3) | |
H1 | 0.7050 (10) | 0.112 (4) | 0.027 (3) | 0.061 (7)* | |
H2 | 0.6190 | 0.1920 | 0.0731 | 0.025* | |
H3 | 0.5373 | 0.2295 | −0.0271 | 0.029* | |
H4 | 0.5121 | 0.5321 | −0.2136 | 0.029* | |
H5 | 0.5695 | 0.7958 | −0.3039 | 0.028* | |
H6 | 0.6516 | 0.7591 | −0.2092 | 0.025* | |
H7 | 0.7964 | 0.8212 | 0.1891 | 0.019* | |
H8 | 0.7787 | 0.2022 | −0.0690 | 0.020* | |
H9 | 0.8583 | 0.0975 | 0.0106 | 0.019* | |
H10 | 0.9386 | 0.1895 | 0.1672 | 0.021* | |
H11 | 0.9869 | 0.4421 | 0.3372 | 0.023* | |
H12 | 0.9557 | 0.8053 | 0.4268 | 0.023* | |
H13 | 0.8766 | 0.9138 | 0.3435 | 0.020* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0197 (5) | 0.0174 (5) | 0.0296 (6) | 0.0001 (4) | 0.0008 (4) | 0.0091 (4) |
O2 | 0.0214 (6) | 0.0145 (5) | 0.0432 (8) | 0.0005 (4) | −0.0023 (5) | 0.0046 (5) |
N1 | 0.0179 (6) | 0.0138 (6) | 0.0219 (7) | −0.0000 (4) | 0.0013 (5) | 0.0046 (5) |
C1 | 0.0176 (7) | 0.0156 (7) | 0.0183 (8) | 0.0024 (5) | 0.0023 (5) | −0.0030 (5) |
C2 | 0.0204 (7) | 0.0192 (7) | 0.0221 (8) | −0.0005 (5) | 0.0018 (6) | 0.0019 (6) |
C3 | 0.0197 (8) | 0.0279 (8) | 0.0258 (9) | −0.0059 (6) | 0.0024 (6) | −0.0004 (6) |
C4 | 0.0167 (7) | 0.0292 (9) | 0.0267 (9) | 0.0018 (6) | −0.0004 (6) | −0.0028 (7) |
C5 | 0.0223 (8) | 0.0223 (8) | 0.0251 (9) | 0.0034 (6) | −0.0015 (6) | 0.0022 (6) |
C6 | 0.0202 (8) | 0.0192 (7) | 0.0242 (8) | 0.0006 (6) | 0.0033 (6) | 0.0022 (6) |
C7 | 0.0189 (7) | 0.0148 (7) | 0.0201 (8) | 0.0004 (5) | 0.0019 (6) | −0.0006 (5) |
C8 | 0.0189 (7) | 0.0117 (6) | 0.0164 (7) | 0.0005 (5) | 0.0051 (5) | 0.0007 (5) |
C9 | 0.0175 (7) | 0.0144 (7) | 0.0172 (7) | −0.0002 (5) | 0.0044 (5) | 0.0029 (5) |
C10 | 0.0199 (7) | 0.0142 (7) | 0.0166 (7) | −0.0027 (5) | 0.0031 (6) | −0.0008 (5) |
C11 | 0.0201 (7) | 0.0121 (6) | 0.0149 (7) | −0.0001 (5) | 0.0051 (5) | −0.0002 (5) |
C12 | 0.0201 (7) | 0.0129 (6) | 0.0118 (7) | −0.0003 (5) | 0.0045 (5) | 0.0031 (5) |
C13 | 0.0198 (7) | 0.0158 (7) | 0.0169 (7) | 0.0013 (5) | 0.0033 (6) | 0.0018 (5) |
C14 | 0.0161 (7) | 0.0232 (8) | 0.0189 (8) | 0.0000 (5) | 0.0010 (6) | 0.0034 (6) |
C15 | 0.0235 (8) | 0.0193 (7) | 0.0148 (7) | −0.0054 (5) | 0.0012 (6) | −0.0002 (6) |
C16 | 0.0239 (7) | 0.0127 (7) | 0.0145 (7) | −0.0026 (5) | 0.0033 (5) | −0.0000 (5) |
C17 | 0.0188 (7) | 0.0131 (6) | 0.0122 (7) | −0.0010 (5) | 0.0039 (5) | 0.0019 (5) |
Geometric parameters (Å, º) top
O1—N1 | 1.4063 (17) | C13—C14 | 1.369 (2) |
O2—C7 | 1.2320 (19) | C14—C15 | 1.415 (2) |
N1—C1 | 1.427 (2) | C15—C16 | 1.367 (2) |
N1—C7 | 1.362 (2) | C16—C17 | 1.419 (2) |
C1—C2 | 1.392 (2) | O1—H1 | 0.96 (2) |
C1—C6 | 1.397 (2) | C2—H2 | 0.950 |
C2—C3 | 1.392 (2) | C3—H3 | 0.950 |
C3—C4 | 1.384 (2) | C4—H4 | 0.950 |
C4—C5 | 1.387 (2) | C5—H5 | 0.950 |
C5—C6 | 1.390 (2) | C6—H6 | 0.950 |
C7—C9 | 1.499 (2) | C8—H7 | 0.950 |
C8—C9 | 1.374 (2) | C10—H8 | 0.950 |
C8—C17 | 1.4163 (19) | C11—H9 | 0.950 |
C9—C10 | 1.422 (2) | C13—H10 | 0.950 |
C10—C11 | 1.369 (2) | C14—H11 | 0.950 |
C11—C12 | 1.418 (2) | C15—H12 | 0.950 |
C12—C13 | 1.420 (2) | C16—H13 | 0.950 |
C12—C17 | 1.420 (2) | | |
| | | |
O1···O2i | 2.7637 (16) | H3···H5i | 3.472 |
O1···N1ii | 3.3787 (18) | H3···H5vii | 3.156 |
O1···C1ii | 3.525 (2) | H3···H5ii | 3.533 |
O2···O1iii | 2.7637 (16) | H3···H5vi | 3.297 |
O2···C8iv | 3.5770 (19) | H4···C3ix | 3.091 |
O2···C10iii | 3.5068 (18) | H4···C3viii | 3.207 |
N1···O1v | 3.3787 (18) | H4···C4vii | 3.394 |
C1···O1v | 3.525 (2) | H4···C4ix | 3.247 |
C8···O2vi | 3.5770 (19) | H4···C5vii | 3.245 |
C8···C11iii | 3.497 (2) | H4···H3ix | 2.629 |
C10···O2i | 3.5068 (18) | H4···H3viii | 2.805 |
C11···C8i | 3.497 (2) | H4···H3v | 3.048 |
C11···C12v | 3.449 (2) | H4···H4vii | 2.944 |
C11···C16i | 3.542 (2) | H4···H4ix | 2.944 |
C11···C17v | 3.447 (2) | H4···H4viii | 3.567 |
C12···C11ii | 3.449 (2) | H4···H5vii | 2.633 |
C12···C16iv | 3.396 (2) | H5···C1iv | 3.272 |
C13···C16i | 3.491 (2) | H5···C2iv | 2.983 |
C16···C11iii | 3.542 (2) | H5···C3iv | 2.925 |
C16···C12vi | 3.396 (2) | H5···C4ix | 3.400 |
C16···C13iii | 3.491 (2) | H5···C4iv | 3.166 |
C16···C17vi | 3.437 (2) | H5···C5iv | 3.438 |
C17···C11ii | 3.447 (2) | H5···C6iv | 3.502 |
C17···C16iv | 3.437 (2) | H5···H2v | 3.264 |
O1···H1ii | 3.49 (2) | H5···H2iv | 3.381 |
O1···H6ii | 3.554 | H5···H3iii | 3.472 |
O1···H6vi | 3.548 | H5···H3ix | 3.156 |
O1···H7i | 3.526 | H5···H3v | 3.533 |
O1···H8ii | 3.222 | H5···H3iv | 3.297 |
O2···H1iii | 1.85 (2) | H5···H4ix | 2.633 |
O2···H6vi | 3.461 | H6···O1v | 3.554 |
O2···H7iv | 3.203 | H6···O1iv | 3.548 |
O2···H8iii | 2.731 | H6···O2iv | 3.461 |
N1···H6vi | 3.175 | H6···N1iv | 3.175 |
C1···H2v | 3.122 | H6···C1iv | 3.162 |
C1···H5vi | 3.272 | H6···C2iv | 3.496 |
C1···H6vi | 3.162 | H6···C7iv | 3.385 |
C2···H2v | 3.430 | H6···H1iii | 3.036 |
C2···H5vi | 2.983 | H6···H1v | 3.406 |
C2···H6vi | 3.496 | H6···H2iii | 3.502 |
C3···H2v | 3.464 | H6···H2v | 3.169 |
C3···H4vii | 3.091 | H7···O1iii | 3.526 |
C3···H4viii | 3.207 | H7···O2vi | 3.203 |
C3···H5vi | 2.925 | H7···C7vi | 3.279 |
C4···H2v | 3.219 | H7···C9vi | 3.149 |
C4···H3ix | 3.377 | H7···C10iii | 3.121 |
C4···H3viii | 3.247 | H7···C10vi | 3.267 |
C4···H3v | 3.141 | H7···C11iii | 3.017 |
C4···H4vii | 3.247 | H7···H1iii | 3.189 |
C4···H4ix | 3.394 | H7···H8iii | 2.993 |
C4···H5vii | 3.400 | H7···H8ii | 3.589 |
C4···H5vi | 3.166 | H7···H8vi | 3.376 |
C5···H2v | 2.878 | H7···H9iii | 2.801 |
C5···H3v | 3.432 | H8···O1v | 3.222 |
C5···H4ix | 3.245 | H8···O2i | 2.731 |
C5···H5vi | 3.438 | H8···C8i | 3.538 |
C6···H2v | 2.820 | H8···C8v | 3.232 |
C6···H5vi | 3.502 | H8···C9v | 3.260 |
C7···H1iii | 2.95 (2) | H8···C10v | 3.542 |
C7···H6vi | 3.385 | H8···C17v | 3.458 |
C7···H7iv | 3.279 | H8···H7i | 2.993 |
C8···H8iii | 3.538 | H8···H7v | 3.589 |
C8···H8ii | 3.232 | H8···H7iv | 3.376 |
C8···H9iii | 3.028 | H8···H13iv | 3.584 |
C8···H9ii | 3.411 | H9···C8i | 3.028 |
C8···H13iv | 3.286 | H9···C8v | 3.411 |
C9···H7iv | 3.149 | H9···C12v | 2.965 |
C9···H8ii | 3.260 | H9···C13v | 3.243 |
C9···H13iv | 3.322 | H9···C14v | 3.288 |
C10···H7i | 3.121 | H9···C15v | 3.070 |
C10···H7iv | 3.267 | H9···C16i | 3.087 |
C10···H8ii | 3.542 | H9···C16v | 2.792 |
C10···H13iv | 3.037 | H9···C17i | 3.143 |
C11···H7i | 3.017 | H9···C17v | 2.721 |
C11···H13i | 3.070 | H9···H7i | 2.801 |
C11···H13iv | 2.719 | H9···H13i | 2.865 |
C12···H9ii | 2.965 | H9···H13v | 3.238 |
C12···H12iv | 3.408 | H9···H13iv | 3.125 |
C12···H13i | 3.116 | H10···C14x | 3.168 |
C12···H13iv | 2.699 | H10···C14v | 3.145 |
C13···H9ii | 3.243 | H10···C15i | 3.142 |
C13···H11x | 3.317 | H10···C15x | 3.503 |
C13···H12i | 3.544 | H10···C15v | 3.325 |
C13···H12x | 3.536 | H10···C16i | 3.026 |
C13···H12iv | 3.169 | H10···H11x | 2.491 |
C13···H13i | 3.003 | H10···H11v | 3.158 |
C13···H13iv | 3.384 | H10···H12i | 3.012 |
C14···H9ii | 3.288 | H10···H12x | 3.153 |
C14···H10xi | 3.168 | H10···H12v | 3.448 |
C14···H10ii | 3.145 | H10···H12iv | 3.495 |
C14···H11xi | 3.300 | H10···H13i | 2.791 |
C14···H11xii | 3.206 | H11···C13xi | 3.317 |
C14···H12x | 3.384 | H11···C14x | 3.300 |
C14···H12xii | 3.548 | H11···C14xii | 3.206 |
C14···H12iv | 3.246 | H11···C15x | 3.072 |
C15···H9ii | 3.070 | H11···C15xii | 3.215 |
C15···H10iii | 3.142 | H11···H10xi | 2.491 |
C15···H10xi | 3.503 | H11···H10ii | 3.158 |
C15···H10ii | 3.325 | H11···H11x | 3.257 |
C15···H11xi | 3.072 | H11···H11xi | 3.257 |
C15···H11xii | 3.215 | H11···H11xii | 2.725 |
C15···H12iv | 3.542 | H11···H12x | 2.863 |
C16···H9iii | 3.087 | H11···H12xii | 2.740 |
C16···H9ii | 2.792 | H12···C12vi | 3.408 |
C16···H10iii | 3.026 | H12···C13iii | 3.544 |
C17···H8ii | 3.458 | H12···C13xi | 3.536 |
C17···H9iii | 3.143 | H12···C13vi | 3.169 |
C17···H9ii | 2.721 | H12···C14xi | 3.384 |
C17···H13iv | 2.997 | H12···C14xii | 3.548 |
H1···O1v | 3.49 (2) | H12···C14vi | 3.246 |
H1···O2i | 1.85 (2) | H12···C15vi | 3.542 |
H1···C7i | 2.95 (2) | H12···H10iii | 3.012 |
H1···H6i | 3.036 | H12···H10xi | 3.153 |
H1···H6ii | 3.406 | H12···H10ii | 3.448 |
H1···H7i | 3.189 | H12···H10vi | 3.495 |
H2···C1ii | 3.122 | H12···H11xi | 2.863 |
H2···C2ii | 3.430 | H12···H11xii | 2.740 |
H2···C3ii | 3.464 | H12···H12xiv | 3.420 |
H2···C4ii | 3.219 | H13···C8vi | 3.286 |
H2···C5ii | 2.878 | H13···C9vi | 3.322 |
H2···C6ii | 2.820 | H13···C10vi | 3.037 |
H2···H5ii | 3.264 | H13···C11iii | 3.070 |
H2···H5vi | 3.381 | H13···C11vi | 2.719 |
H2···H6i | 3.502 | H13···C12iii | 3.116 |
H2···H6ii | 3.169 | H13···C12vi | 2.699 |
H3···C4vii | 3.377 | H13···C13iii | 3.003 |
H3···C4viii | 3.247 | H13···C13vi | 3.384 |
H3···C4ii | 3.141 | H13···C17vi | 2.997 |
H3···C5ii | 3.432 | H13···H8vi | 3.584 |
H3···H3xiii | 3.360 | H13···H9iii | 2.865 |
H3···H4vii | 2.629 | H13···H9ii | 3.238 |
H3···H4viii | 2.805 | H13···H9vi | 3.125 |
H3···H4ii | 3.048 | H13···H10iii | 2.791 |
| | | |
O1—N1—C1 | 115.17 (11) | C8—C17—C16 | 121.81 (13) |
O1—N1—C7 | 115.50 (12) | C12—C17—C16 | 119.16 (13) |
C1—N1—C7 | 127.22 (12) | N1—O1—H1 | 104.5 (17) |
N1—C1—C2 | 118.62 (13) | C1—C2—H2 | 120.3 |
N1—C1—C6 | 121.30 (14) | C3—C2—H2 | 120.2 |
C2—C1—C6 | 120.01 (14) | C2—C3—H3 | 119.5 |
C1—C2—C3 | 119.51 (14) | C4—C3—H3 | 119.5 |
C2—C3—C4 | 120.96 (15) | C3—C4—H4 | 120.4 |
C3—C4—C5 | 119.13 (15) | C5—C4—H4 | 120.4 |
C4—C5—C6 | 120.99 (15) | C4—C5—H5 | 119.5 |
C1—C6—C5 | 119.38 (15) | C6—C5—H5 | 119.5 |
O2—C7—N1 | 122.06 (14) | C1—C6—H6 | 120.3 |
O2—C7—C9 | 120.62 (14) | C5—C6—H6 | 120.3 |
N1—C7—C9 | 117.30 (13) | C9—C8—H7 | 119.6 |
C9—C8—C17 | 120.79 (13) | C17—C8—H7 | 119.6 |
C7—C9—C8 | 117.48 (13) | C9—C10—H8 | 120.0 |
C7—C9—C10 | 122.24 (13) | C11—C10—H8 | 120.0 |
C8—C9—C10 | 120.12 (14) | C10—C11—H9 | 119.5 |
C9—C10—C11 | 120.01 (13) | C12—C11—H9 | 119.5 |
C10—C11—C12 | 120.93 (14) | C12—C13—H10 | 119.7 |
C11—C12—C13 | 122.08 (13) | C14—C13—H10 | 119.7 |
C11—C12—C17 | 119.09 (14) | C13—C14—H11 | 119.8 |
C13—C12—C17 | 118.82 (13) | C15—C14—H11 | 119.8 |
C12—C13—C14 | 120.68 (14) | C14—C15—H12 | 119.9 |
C13—C14—C15 | 120.38 (14) | C16—C15—H12 | 119.9 |
C14—C15—C16 | 120.28 (14) | C15—C16—H13 | 119.7 |
C15—C16—C17 | 120.68 (13) | C17—C16—H13 | 119.7 |
C8—C17—C12 | 119.03 (13) | | |
| | | |
O1—N1—C1—C2 | 2.1 (2) | C9—C8—C17—C12 | 0.6 (2) |
O1—N1—C1—C6 | −174.89 (14) | C9—C8—C17—C16 | −179.30 (15) |
O1—N1—C7—O2 | −159.62 (14) | C17—C8—C9—C7 | −177.22 (14) |
O1—N1—C7—C9 | 21.9 (2) | C17—C8—C9—C10 | −1.7 (2) |
C1—N1—C7—O2 | 2.9 (2) | C7—C9—C10—C11 | 176.81 (15) |
C1—N1—C7—C9 | −175.50 (14) | C8—C9—C10—C11 | 1.5 (2) |
C7—N1—C1—C2 | −160.51 (15) | C9—C10—C11—C12 | −0.2 (2) |
C7—N1—C1—C6 | 22.5 (2) | C10—C11—C12—C13 | 179.83 (15) |
N1—C1—C2—C3 | −177.55 (14) | C10—C11—C12—C17 | −0.8 (2) |
N1—C1—C6—C5 | 177.99 (15) | C11—C12—C13—C14 | 179.96 (12) |
C2—C1—C6—C5 | 1.0 (2) | C11—C12—C17—C8 | 0.6 (2) |
C6—C1—C2—C3 | −0.5 (2) | C11—C12—C17—C16 | −179.45 (14) |
C1—C2—C3—C4 | −0.3 (2) | C13—C12—C17—C8 | −179.99 (12) |
C2—C3—C4—C5 | 0.6 (2) | C13—C12—C17—C16 | −0.1 (2) |
C3—C4—C5—C6 | −0.1 (2) | C17—C12—C13—C14 | 0.6 (2) |
C4—C5—C6—C1 | −0.8 (2) | C12—C13—C14—C15 | −0.4 (2) |
O2—C7—C9—C8 | 40.8 (2) | C13—C14—C15—C16 | −0.3 (2) |
O2—C7—C9—C10 | −134.64 (17) | C14—C15—C16—C17 | 0.8 (2) |
N1—C7—C9—C8 | −140.73 (15) | C15—C16—C17—C8 | 179.28 (15) |
N1—C7—C9—C10 | 43.8 (2) | C15—C16—C17—C12 | −0.6 (2) |
Symmetry codes: (i) x, y−1, z; (ii) x, −y+1/2, z+1/2; (iii) x, y+1, z; (iv) x, −y+3/2, z−1/2; (v) x, −y+1/2, z−1/2; (vi) x, −y+3/2, z+1/2; (vii) −x+1, y−1/2, −z−1/2; (viii) −x+1, −y+1, −z; (ix) −x+1, y+1/2, −z−1/2; (x) −x+2, y−1/2, −z+1/2; (xi) −x+2, y+1/2, −z+1/2; (xii) −x+2, −y+1, −z+1; (xiii) −x+1, −y, −z; (xiv) −x+2, −y+2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.96 (2) | 1.85 (2) | 2.7637 (16) | 157 (2) |
C2—H2···Cg1ii | 0.95 | 2.84 | 3.618 (2) | 139 |
C5—H5···Cg1iv | 0.95 | 2.91 | 3.690 (2) | 141 |
C11—H9···Cg3v | 0.95 | 2.68 | 3.430 (2) | 137 |
C16—H13···Cg2vi | 0.95 | 2.67 | 3.394 (2) | 133 |
Symmetry codes: (i) x, y−1, z; (ii) x, −y+1/2, z+1/2; (iv) x, −y+3/2, z−1/2; (v) x, −y+1/2, z−1/2; (vi) x, −y+3/2, z+1/2. |
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