Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807030668/hb2457sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807030668/hb2457Isup2.hkl |
CCDC reference: 655055
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.005 Å
- Disorder in main residue
- R factor = 0.063
- wR factor = 0.183
- Data-to-parameter ratio = 14.4
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 36 Perc. PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C20 PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C21'
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 200 Deg. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.32 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.74 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C14 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C19 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18' PLAT301_ALERT_3_C Main Residue Disorder ......................... 14.00 Perc. PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C12 -C17 1.36 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C25 - C26 ... 1.43 Ang. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 43.80 Deg. C18 -N3 -C18' 1.555 1.555 1.555
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 83
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 10 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 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
checkCIF publication errors
Alert level G PUBL013_ALERT_1_G The _publ_section_comment (discussion of study) is missing. This is required for a full paper submission (but is optional for an electronic paper).
0 ALERT level A = Data missing that is essential or data in wrong format 1 ALERT level G = General alerts. Data that may be required is missing
For a related structure, see: Sun et al. (2006). For the synthesis, see: Ding et al. (2001).
The compound was synthesized according to a reported procedure (Ding et al., 2001) and yellow blocks of (I) were grown from a dichloromethane/ diethyl ether solution (1:1 v/v) in about 75% yield. Analysis calculated for C27H35N3O2: C 74.79, H 8.14, N 9.69%; found: C 74.85, H 8.36, N 9.79%.
It is analogous to the examples (Sun et al., 2006), the pentyl chain (C18 to C12) is disordered over two positions; the occupancy factors refined to 0.52 (1):0.48 (1). The pairs of 1,2-related and 1,3- related distances were restrained to be equal within 0.01 Å. The H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
For a related structure, see: Sun et al. (2006). For the synthesis, see: Ding et al. (2001).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.
Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level. H atoms are drawn as spheres of arbitrary radius. |
C27H35N3O2 | Z = 2 |
Mr = 433.58 | F(000) = 468 |
Triclinic, P1 | Dx = 1.150 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.4091 (8) Å | Cell parameters from 1232 reflections |
b = 11.4405 (9) Å | θ = 2.6–19.1° |
c = 11.9354 (10) Å | µ = 0.07 mm−1 |
α = 90.080 (2)° | T = 292 K |
β = 94.746 (2)° | Block, yellow |
γ = 102.044 (2)° | 0.20 × 0.10 × 0.10 mm |
V = 1251.96 (18) Å3 |
Bruker SMART CCD diffractometer | 1734 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.085 |
Graphite monochromator | θmax = 26.0°, θmin = 1.7° |
ω scans | h = −11→11 |
10980 measured reflections | k = −14→14 |
4871 independent reflections | l = −14→14 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.183 | H-atom parameters constrained |
S = 0.82 | w = 1/[σ2(Fo2) + (0.0792P)2] where P = (Fo2 + 2Fc2)/3 |
4871 reflections | (Δ/σ)max = 0.001 |
339 parameters | Δρmax = 0.19 e Å−3 |
83 restraints | Δρmin = −0.16 e Å−3 |
C27H35N3O2 | γ = 102.044 (2)° |
Mr = 433.58 | V = 1251.96 (18) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.4091 (8) Å | Mo Kα radiation |
b = 11.4405 (9) Å | µ = 0.07 mm−1 |
c = 11.9354 (10) Å | T = 292 K |
α = 90.080 (2)° | 0.20 × 0.10 × 0.10 mm |
β = 94.746 (2)° |
Bruker SMART CCD diffractometer | 1734 reflections with I > 2σ(I) |
10980 measured reflections | Rint = 0.085 |
4871 independent reflections |
R[F2 > 2σ(F2)] = 0.063 | 83 restraints |
wR(F2) = 0.183 | H-atom parameters constrained |
S = 0.82 | Δρmax = 0.19 e Å−3 |
4871 reflections | Δρmin = −0.16 e Å−3 |
339 parameters |
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 | Occ. (<1) | |
C1 | 0.3373 (4) | −0.0641 (3) | 0.0797 (3) | 0.1419 (15) | |
H1A | 0.4238 | −0.0957 | 0.0775 | 0.213* | |
H1B | 0.2829 | −0.0752 | 0.0075 | 0.213* | |
H1C | 0.2784 | −0.1050 | 0.1354 | 0.213* | |
C2 | 0.4595 (4) | 0.0944 (3) | 0.2069 (3) | 0.0871 (9) | |
C3 | 0.5044 (4) | 0.0181 (3) | 0.2825 (3) | 0.0984 (10) | |
H3 | 0.4800 | −0.0639 | 0.2682 | 0.118* | |
C4 | 0.4948 (3) | 0.2159 (3) | 0.2300 (3) | 0.0904 (9) | |
H4 | 0.4625 | 0.2683 | 0.1792 | 0.108* | |
C5 | 0.5858 (4) | 0.0625 (3) | 0.3799 (3) | 0.0947 (10) | |
H5 | 0.6155 | 0.0090 | 0.4308 | 0.114* | |
C6 | 0.5773 (3) | 0.2601 (2) | 0.3273 (3) | 0.0832 (9) | |
H6 | 0.6012 | 0.3422 | 0.3410 | 0.100* | |
C7 | 0.6254 (3) | 0.1840 (2) | 0.4055 (2) | 0.0731 (8) | |
C8 | 0.7086 (3) | 0.2258 (3) | 0.5116 (2) | 0.0807 (8) | |
H8 | 0.7259 | 0.1663 | 0.5607 | 0.097* | |
C9 | 0.7640 (3) | 0.3391 (3) | 0.5486 (2) | 0.0752 (8) | |
C10 | 0.8344 (3) | 0.3676 (3) | 0.6628 (3) | 0.0859 (9) | |
C11 | 0.8180 (3) | 0.5311 (3) | 0.5639 (2) | 0.0794 (8) | |
C12 | 0.9303 (4) | 0.5560 (2) | 0.7692 (2) | 0.0768 (8) | |
C13 | 0.8467 (4) | 0.5797 (3) | 0.8493 (3) | 0.1260 (14) | |
H13 | 0.7455 | 0.5582 | 0.8379 | 0.151* | |
C14 | 0.9134 (6) | 0.6367 (4) | 0.9495 (3) | 0.1468 (18) | |
H14 | 0.8568 | 0.6538 | 1.0052 | 0.176* | |
C15 | 1.0587 (7) | 0.6665 (3) | 0.9650 (3) | 0.1258 (15) | |
H15 | 1.1035 | 0.7024 | 1.0325 | 0.151* | |
C16 | 1.1403 (5) | 0.6449 (3) | 0.8832 (4) | 0.1293 (14) | |
H16 | 1.2412 | 0.6694 | 0.8933 | 0.155* | |
C17 | 1.0779 (4) | 0.5880 (3) | 0.7863 (3) | 0.1041 (11) | |
H17 | 1.1359 | 0.5708 | 0.7317 | 0.125* | |
C18' | 0.8293 (7) | 0.7435 (5) | 0.6198 (5) | 0.087 (2) | 0.48 |
H18C | 0.8159 | 0.7106 | 0.6939 | 0.104* | 0.48 |
H18D | 0.7496 | 0.7828 | 0.5982 | 0.104* | 0.48 |
C19' | 0.9726 (10) | 0.8314 (6) | 0.6210 (8) | 0.125 (3) | 0.48 |
H19C | 1.0468 | 0.7937 | 0.6578 | 0.150* | 0.48 |
H19D | 0.9954 | 0.8440 | 0.5436 | 0.150* | 0.48 |
C20' | 0.9882 (14) | 0.9510 (7) | 0.6752 (8) | 0.138 (4) | 0.48 |
H20C | 1.0740 | 1.0027 | 0.6492 | 0.165* | 0.48 |
H20D | 0.9047 | 0.9834 | 0.6476 | 0.165* | 0.48 |
C21' | 1.0005 (15) | 0.9595 (9) | 0.7999 (6) | 0.179 (6) | 0.48 |
H21C | 1.0571 | 0.9026 | 0.8288 | 0.215* | 0.48 |
H21D | 0.9035 | 0.9350 | 0.8251 | 0.215* | 0.48 |
C22' | 1.0690 (16) | 1.0806 (11) | 0.8523 (10) | 0.127 (5) | 0.48 |
H22D | 1.0833 | 1.0734 | 0.9324 | 0.191* | 0.48 |
H22E | 1.0059 | 1.1352 | 0.8350 | 0.191* | 0.48 |
H22F | 1.1614 | 1.1100 | 0.8228 | 0.191* | 0.48 |
C18 | 0.9372 (8) | 0.7502 (5) | 0.5874 (6) | 0.098 (2) | 0.52 |
H18A | 0.9942 | 0.7232 | 0.6497 | 0.118* | 0.52 |
H18B | 1.0036 | 0.7828 | 0.5318 | 0.118* | 0.52 |
C19 | 0.8732 (10) | 0.8431 (6) | 0.6270 (8) | 0.123 (3) | 0.52 |
H19A | 0.8397 | 0.8795 | 0.5592 | 0.148* | 0.52 |
H19B | 0.7857 | 0.8015 | 0.6590 | 0.148* | 0.52 |
C20 | 0.9297 (13) | 0.9400 (13) | 0.7014 (16) | 0.240 (10) | 0.52 |
H20A | 0.9033 | 1.0073 | 0.6617 | 0.288* | 0.52 |
H20B | 0.8665 | 0.9254 | 0.7623 | 0.288* | 0.52 |
C21 | 1.0651 (13) | 0.9887 (14) | 0.7559 (12) | 0.208 (6) | 0.52 |
H21A | 1.1263 | 1.0165 | 0.6957 | 0.249* | 0.52 |
H21B | 1.0999 | 0.9205 | 0.7870 | 0.249* | 0.52 |
C22 | 1.108 (2) | 1.0790 (17) | 0.8408 (15) | 0.242 (10) | 0.52 |
H22A | 1.1578 | 1.1512 | 0.8086 | 0.363* | 0.52 |
H22B | 1.1710 | 1.0534 | 0.8985 | 0.363* | 0.52 |
H22C | 1.0224 | 1.0937 | 0.8729 | 0.363* | 0.52 |
C23 | 0.7827 (4) | 0.6700 (3) | 0.4173 (3) | 0.1040 (11) | |
H23A | 0.8301 | 0.7500 | 0.3974 | 0.125* | |
H23B | 0.8116 | 0.6138 | 0.3674 | 0.125* | |
C24 | 0.6236 (4) | 0.6580 (3) | 0.4021 (3) | 0.1162 (12) | |
H24A | 0.5943 | 0.7109 | 0.4553 | 0.139* | |
H24B | 0.5764 | 0.5767 | 0.4180 | 0.139* | |
C25 | 0.5719 (4) | 0.6892 (4) | 0.2796 (3) | 0.1317 (13) | |
H25A | 0.4689 | 0.6902 | 0.2780 | 0.158* | |
H25B | 0.6225 | 0.7701 | 0.2653 | 0.158* | |
C26 | 0.5905 (5) | 0.6148 (4) | 0.1874 (4) | 0.1422 (14) | |
H26A | 0.5425 | 0.5329 | 0.2005 | 0.171* | |
H26B | 0.6937 | 0.6168 | 0.1839 | 0.171* | |
C27 | 0.5287 (5) | 0.6542 (4) | 0.0760 (3) | 0.1611 (17) | |
H27A | 0.4270 | 0.6538 | 0.0796 | 0.242* | |
H27B | 0.5400 | 0.6004 | 0.0173 | 0.242* | |
H27C | 0.5798 | 0.7335 | 0.0606 | 0.242* | |
N1 | 0.7605 (3) | 0.4446 (2) | 0.49258 (18) | 0.0801 (7) | |
N2 | 0.8658 (3) | 0.4919 (2) | 0.66852 (19) | 0.0875 (7) | |
N3 | 0.8318 (3) | 0.6467 (2) | 0.5371 (2) | 0.0950 (8) | |
O1 | 0.3769 (3) | 0.06040 (19) | 0.10780 (19) | 0.1136 (8) | |
O2 | 0.8609 (3) | 0.30362 (19) | 0.73927 (19) | 0.1186 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.166 (4) | 0.101 (3) | 0.138 (3) | −0.005 (3) | −0.017 (3) | −0.050 (2) |
C2 | 0.091 (2) | 0.080 (2) | 0.087 (2) | 0.0093 (19) | 0.0058 (19) | −0.0139 (19) |
C3 | 0.111 (3) | 0.070 (2) | 0.110 (3) | 0.0121 (19) | 0.002 (2) | −0.021 (2) |
C4 | 0.107 (3) | 0.081 (2) | 0.079 (2) | 0.0159 (18) | −0.0001 (19) | −0.0028 (16) |
C5 | 0.111 (3) | 0.069 (2) | 0.105 (3) | 0.0264 (18) | 0.000 (2) | −0.0029 (17) |
C6 | 0.101 (2) | 0.0652 (18) | 0.079 (2) | 0.0088 (17) | 0.0034 (18) | −0.0037 (16) |
C7 | 0.078 (2) | 0.0677 (18) | 0.074 (2) | 0.0152 (16) | 0.0118 (16) | −0.0046 (15) |
C8 | 0.095 (2) | 0.076 (2) | 0.0747 (19) | 0.0267 (17) | 0.0086 (17) | 0.0047 (15) |
C9 | 0.085 (2) | 0.074 (2) | 0.0669 (18) | 0.0194 (16) | 0.0024 (16) | −0.0043 (15) |
C10 | 0.103 (2) | 0.080 (2) | 0.073 (2) | 0.0230 (19) | −0.0073 (18) | −0.0016 (17) |
C11 | 0.102 (2) | 0.070 (2) | 0.0651 (19) | 0.0179 (17) | −0.0036 (17) | −0.0034 (16) |
C12 | 0.080 (2) | 0.083 (2) | 0.0642 (19) | 0.0133 (18) | −0.0056 (17) | −0.0074 (15) |
C13 | 0.098 (3) | 0.143 (3) | 0.128 (3) | −0.005 (2) | 0.032 (3) | −0.053 (3) |
C14 | 0.182 (5) | 0.133 (3) | 0.109 (3) | −0.027 (3) | 0.066 (3) | −0.044 (3) |
C15 | 0.174 (5) | 0.110 (3) | 0.071 (3) | −0.011 (3) | −0.018 (3) | −0.005 (2) |
C16 | 0.115 (3) | 0.141 (3) | 0.123 (4) | 0.021 (3) | −0.028 (3) | −0.028 (3) |
C17 | 0.091 (3) | 0.113 (3) | 0.104 (3) | 0.016 (2) | −0.002 (2) | −0.030 (2) |
C18' | 0.096 (5) | 0.085 (5) | 0.083 (4) | 0.027 (4) | 0.006 (4) | −0.003 (4) |
C19' | 0.132 (7) | 0.102 (6) | 0.139 (7) | 0.024 (6) | 0.000 (6) | −0.019 (5) |
C20' | 0.140 (7) | 0.104 (6) | 0.147 (7) | −0.014 (5) | −0.015 (6) | −0.067 (5) |
C21' | 0.149 (10) | 0.233 (14) | 0.144 (11) | 0.007 (10) | 0.032 (9) | 0.084 (11) |
C22' | 0.146 (9) | 0.113 (8) | 0.106 (7) | 0.003 (7) | −0.023 (6) | −0.074 (7) |
C18 | 0.118 (6) | 0.084 (4) | 0.085 (4) | 0.005 (4) | 0.006 (4) | −0.008 (4) |
C19 | 0.149 (7) | 0.081 (5) | 0.133 (6) | 0.008 (5) | 0.021 (5) | −0.049 (4) |
C20 | 0.209 (12) | 0.205 (13) | 0.206 (13) | 0.041 (8) | 0.050 (9) | −0.004 (9) |
C21 | 0.229 (10) | 0.221 (10) | 0.167 (9) | 0.020 (8) | 0.049 (8) | −0.038 (8) |
C22 | 0.228 (16) | 0.228 (15) | 0.253 (16) | −0.017 (11) | 0.079 (12) | 0.059 (12) |
C23 | 0.129 (3) | 0.075 (2) | 0.106 (3) | 0.016 (2) | 0.016 (2) | 0.0037 (17) |
C24 | 0.108 (3) | 0.117 (3) | 0.128 (3) | 0.035 (2) | 0.008 (3) | 0.005 (2) |
C25 | 0.130 (3) | 0.153 (4) | 0.119 (3) | 0.050 (3) | −0.003 (3) | 0.021 (3) |
C26 | 0.168 (4) | 0.136 (3) | 0.123 (3) | 0.041 (3) | −0.012 (3) | −0.014 (3) |
C27 | 0.207 (5) | 0.170 (4) | 0.098 (3) | 0.040 (3) | −0.040 (3) | 0.008 (3) |
N1 | 0.1053 (19) | 0.0673 (15) | 0.0648 (14) | 0.0161 (13) | −0.0039 (13) | −0.0020 (13) |
N2 | 0.113 (2) | 0.0755 (17) | 0.0702 (16) | 0.0211 (14) | −0.0194 (14) | −0.0090 (13) |
N3 | 0.136 (2) | 0.0739 (18) | 0.0695 (17) | 0.0192 (16) | −0.0171 (15) | −0.0067 (13) |
O1 | 0.1251 (19) | 0.1029 (17) | 0.1018 (17) | 0.0084 (14) | −0.0134 (14) | −0.0250 (13) |
O2 | 0.169 (2) | 0.0942 (16) | 0.0889 (16) | 0.0336 (15) | −0.0292 (15) | 0.0069 (13) |
C1—O1 | 1.427 (3) | C19'—H19D | 0.9700 |
C1—H1A | 0.9600 | C20'—C21' | 1.485 (8) |
C1—H1B | 0.9600 | C20'—H20C | 0.9700 |
C1—H1C | 0.9600 | C20'—H20D | 0.9700 |
C2—C3 | 1.359 (4) | C21'—C22' | 1.511 (8) |
C2—O1 | 1.370 (3) | C21'—H21C | 0.9700 |
C2—C4 | 1.382 (4) | C21'—H21D | 0.9700 |
C3—C5 | 1.373 (4) | C22'—H22D | 0.9600 |
C3—H3 | 0.9300 | C22'—H22E | 0.9600 |
C4—C6 | 1.376 (4) | C22'—H22F | 0.9600 |
C4—H4 | 0.9300 | C18—C19 | 1.424 (7) |
C5—C7 | 1.389 (4) | C18—N3 | 1.469 (6) |
C5—H5 | 0.9300 | C18—H18A | 0.9700 |
C6—C7 | 1.389 (4) | C18—H18B | 0.9700 |
C6—H6 | 0.9300 | C19—C20 | 1.404 (6) |
C7—C8 | 1.457 (4) | C19—H19A | 0.9700 |
C8—C9 | 1.351 (3) | C19—H19B | 0.9700 |
C8—H8 | 0.9300 | C20—C21 | 1.387 (8) |
C9—N1 | 1.385 (3) | C20—H20A | 0.9700 |
C9—C10 | 1.470 (4) | C20—H20B | 0.9700 |
C10—O2 | 1.213 (3) | C21—C22 | 1.419 (8) |
C10—N2 | 1.392 (3) | C21—H21A | 0.9700 |
C11—N1 | 1.302 (3) | C21—H21B | 0.9700 |
C11—N3 | 1.343 (3) | C22—H22A | 0.9600 |
C11—N2 | 1.398 (3) | C22—H22B | 0.9600 |
C12—C13 | 1.348 (4) | C22—H22C | 0.9600 |
C12—C17 | 1.359 (4) | C23—C24 | 1.471 (4) |
C12—N2 | 1.429 (3) | C23—N3 | 1.508 (4) |
C13—C14 | 1.398 (5) | C23—H23A | 0.9700 |
C13—H13 | 0.9300 | C23—H23B | 0.9700 |
C14—C15 | 1.336 (5) | C24—C25 | 1.569 (5) |
C14—H14 | 0.9300 | C24—H24A | 0.9700 |
C15—C16 | 1.344 (5) | C24—H24B | 0.9700 |
C15—H15 | 0.9300 | C25—C26 | 1.434 (5) |
C16—C17 | 1.353 (4) | C25—H25A | 0.9700 |
C16—H16 | 0.9300 | C25—H25B | 0.9700 |
C17—H17 | 0.9300 | C26—C27 | 1.515 (5) |
C18'—N3 | 1.488 (6) | C26—H26A | 0.9700 |
C18'—C19' | 1.503 (7) | C26—H26B | 0.9700 |
C18'—H18C | 0.9700 | C27—H27A | 0.9600 |
C18'—H18D | 0.9700 | C27—H27B | 0.9600 |
C19'—C20' | 1.487 (7) | C27—H27C | 0.9600 |
C19'—H19C | 0.9700 | ||
O1—C1—H1A | 109.5 | C20'—C21'—H21D | 108.1 |
O1—C1—H1B | 109.5 | C22'—C21'—H21D | 108.1 |
H1A—C1—H1B | 109.5 | H21C—C21'—H21D | 107.3 |
O1—C1—H1C | 109.5 | C21'—C22'—H22D | 109.5 |
H1A—C1—H1C | 109.5 | C21'—C22'—H22E | 109.5 |
H1B—C1—H1C | 109.5 | H22D—C22'—H22E | 109.5 |
C3—C2—O1 | 124.9 (3) | C21'—C22'—H22F | 109.5 |
C3—C2—C4 | 119.4 (3) | H22D—C22'—H22F | 109.5 |
O1—C2—C4 | 115.7 (3) | H22E—C22'—H22F | 109.5 |
C2—C3—C5 | 119.8 (3) | C19—C18—N3 | 114.4 (6) |
C2—C3—H3 | 120.1 | C19—C18—H18A | 108.7 |
C5—C3—H3 | 120.1 | N3—C18—H18A | 108.7 |
C6—C4—C2 | 120.6 (3) | C19—C18—H18B | 108.7 |
C6—C4—H4 | 119.7 | N3—C18—H18B | 108.7 |
C2—C4—H4 | 119.7 | H18A—C18—H18B | 107.6 |
C3—C5—C7 | 122.6 (3) | C20—C19—C18 | 131.3 (7) |
C3—C5—H5 | 118.7 | C20—C19—H19A | 104.4 |
C7—C5—H5 | 118.7 | C18—C19—H19A | 104.4 |
C4—C6—C7 | 121.1 (3) | C20—C19—H19B | 104.4 |
C4—C6—H6 | 119.5 | C18—C19—H19B | 104.4 |
C7—C6—H6 | 119.5 | H19A—C19—H19B | 105.6 |
C6—C7—C5 | 116.5 (3) | C21—C20—C19 | 135.7 (9) |
C6—C7—C8 | 123.3 (3) | C21—C20—H20A | 103.3 |
C5—C7—C8 | 120.2 (3) | C19—C20—H20A | 103.3 |
C9—C8—C7 | 128.9 (3) | C21—C20—H20B | 103.3 |
C9—C8—H8 | 115.5 | C19—C20—H20B | 103.3 |
C7—C8—H8 | 115.5 | H20A—C20—H20B | 105.2 |
C8—C9—N1 | 128.3 (3) | C20—C21—C22 | 131.1 (12) |
C8—C9—C10 | 122.5 (3) | C20—C21—H21A | 104.5 |
N1—C9—C10 | 109.1 (2) | C22—C21—H21A | 104.5 |
O2—C10—N2 | 124.6 (3) | C20—C21—H21B | 104.5 |
O2—C10—C9 | 131.3 (3) | C22—C21—H21B | 104.5 |
N2—C10—C9 | 104.0 (3) | H21A—C21—H21B | 105.6 |
N1—C11—N3 | 122.3 (3) | C24—C23—N3 | 111.1 (3) |
N1—C11—N2 | 113.7 (2) | C24—C23—H23A | 109.4 |
N3—C11—N2 | 124.0 (3) | N3—C23—H23A | 109.4 |
C13—C12—C17 | 120.0 (3) | C24—C23—H23B | 109.4 |
C13—C12—N2 | 120.7 (3) | N3—C23—H23B | 109.4 |
C17—C12—N2 | 119.2 (3) | H23A—C23—H23B | 108.0 |
C12—C13—C14 | 119.4 (4) | C23—C24—C25 | 111.7 (3) |
C12—C13—H13 | 120.3 | C23—C24—H24A | 109.3 |
C14—C13—H13 | 120.3 | C25—C24—H24A | 109.3 |
C15—C14—C13 | 119.7 (4) | C23—C24—H24B | 109.3 |
C15—C14—H14 | 120.1 | C25—C24—H24B | 109.3 |
C13—C14—H14 | 120.1 | H24A—C24—H24B | 107.9 |
C14—C15—C16 | 120.1 (4) | C26—C25—C24 | 119.1 (3) |
C14—C15—H15 | 120.0 | C26—C25—H25A | 107.5 |
C16—C15—H15 | 120.0 | C24—C25—H25A | 107.5 |
C15—C16—C17 | 121.0 (4) | C26—C25—H25B | 107.5 |
C15—C16—H16 | 119.5 | C24—C25—H25B | 107.5 |
C17—C16—H16 | 119.5 | H25A—C25—H25B | 107.0 |
C16—C17—C12 | 119.7 (3) | C25—C26—C27 | 112.2 (4) |
C16—C17—H17 | 120.1 | C25—C26—H26A | 109.2 |
C12—C17—H17 | 120.1 | C27—C26—H26A | 109.2 |
N3—C18'—C19' | 107.7 (6) | C25—C26—H26B | 109.2 |
N3—C18'—H18C | 110.2 | C27—C26—H26B | 109.2 |
C19'—C18'—H18C | 110.2 | H26A—C26—H26B | 107.9 |
N3—C18'—H18D | 110.2 | C26—C27—H27A | 109.5 |
C19'—C18'—H18D | 110.2 | C26—C27—H27B | 109.5 |
H18C—C18'—H18D | 108.5 | H27A—C27—H27B | 109.5 |
C20'—C19'—C18' | 119.3 (8) | C26—C27—H27C | 109.5 |
C20'—C19'—H19C | 107.5 | H27A—C27—H27C | 109.5 |
C18'—C19'—H19C | 107.5 | H27B—C27—H27C | 109.5 |
C20'—C19'—H19D | 107.5 | C11—N1—C9 | 106.4 (2) |
C18'—C19'—H19D | 107.5 | C10—N2—C11 | 106.7 (2) |
H19C—C19'—H19D | 107.0 | C10—N2—C12 | 121.7 (2) |
C21'—C20'—C19' | 118.4 (8) | C11—N2—C12 | 131.5 (2) |
C21'—C20'—H20C | 107.7 | C11—N3—C18 | 128.1 (4) |
C19'—C20'—H20C | 107.7 | C11—N3—C18' | 123.8 (3) |
C21'—C20'—H20D | 107.7 | C18—N3—C18' | 43.8 (3) |
C19'—C20'—H20D | 107.7 | C11—N3—C23 | 115.7 (2) |
H20C—C20'—H20D | 107.1 | C18—N3—C23 | 111.2 (3) |
C20'—C21'—C22' | 116.6 (9) | C18'—N3—C23 | 115.3 (3) |
C20'—C21'—H21C | 108.1 | C2—O1—C1 | 118.0 (3) |
C22'—C21'—H21C | 108.1 | ||
O1—C2—C3—C5 | −179.3 (3) | C24—C25—C26—C27 | 177.4 (4) |
C4—C2—C3—C5 | −0.9 (5) | N3—C11—N1—C9 | −179.9 (3) |
C3—C2—C4—C6 | 1.4 (5) | N2—C11—N1—C9 | 1.3 (3) |
O1—C2—C4—C6 | 179.9 (3) | C8—C9—N1—C11 | 175.6 (3) |
C2—C3—C5—C7 | −0.1 (5) | C10—C9—N1—C11 | −1.7 (3) |
C2—C4—C6—C7 | −0.9 (4) | O2—C10—N2—C11 | −179.8 (3) |
C4—C6—C7—C5 | −0.1 (4) | C9—C10—N2—C11 | −0.7 (3) |
C4—C6—C7—C8 | −177.8 (3) | O2—C10—N2—C12 | −1.7 (5) |
C3—C5—C7—C6 | 0.6 (4) | C9—C10—N2—C12 | 177.3 (3) |
C3—C5—C7—C8 | 178.3 (3) | N1—C11—N2—C10 | −0.3 (3) |
C6—C7—C8—C9 | −6.6 (5) | N3—C11—N2—C10 | −179.1 (3) |
C5—C7—C8—C9 | 175.8 (3) | N1—C11—N2—C12 | −178.1 (3) |
C7—C8—C9—N1 | −2.8 (5) | N3—C11—N2—C12 | 3.1 (5) |
C7—C8—C9—C10 | 174.1 (3) | C13—C12—N2—C10 | −86.3 (4) |
C8—C9—C10—O2 | 3.0 (5) | C17—C12—N2—C10 | 90.5 (4) |
N1—C9—C10—O2 | −179.5 (3) | C13—C12—N2—C11 | 91.3 (4) |
C8—C9—C10—N2 | −176.0 (2) | C17—C12—N2—C11 | −92.0 (4) |
N1—C9—C10—N2 | 1.5 (3) | N1—C11—N3—C18 | −155.0 (4) |
C17—C12—C13—C14 | −0.2 (5) | N2—C11—N3—C18 | 23.7 (6) |
N2—C12—C13—C14 | 176.5 (3) | N1—C11—N3—C18' | 150.4 (4) |
C12—C13—C14—C15 | −0.3 (6) | N2—C11—N3—C18' | −30.9 (5) |
C13—C14—C15—C16 | 1.9 (7) | N1—C11—N3—C23 | −2.8 (4) |
C14—C15—C16—C17 | −3.1 (7) | N2—C11—N3—C23 | 175.9 (3) |
C15—C16—C17—C12 | 2.5 (6) | C19—C18—N3—C11 | −125.9 (6) |
C13—C12—C17—C16 | −0.9 (5) | C19—C18—N3—C18' | −24.2 (6) |
N2—C12—C17—C16 | −177.6 (3) | C19—C18—N3—C23 | 80.8 (7) |
N3—C18'—C19'—C20' | 165.8 (7) | C19'—C18'—N3—C11 | 119.8 (6) |
C18'—C19'—C20'—C21' | 74.3 (14) | C19'—C18'—N3—C18 | 7.8 (6) |
C19'—C20'—C21'—C22' | 158.6 (11) | C19'—C18'—N3—C23 | −87.0 (6) |
N3—C18—C19—C20 | 162.9 (15) | C24—C23—N3—C11 | 81.5 (3) |
C18—C19—C20—C21 | 7 (4) | C24—C23—N3—C18 | −121.7 (4) |
C19—C20—C21—C22 | −171.2 (18) | C24—C23—N3—C18' | −73.9 (4) |
N3—C23—C24—C25 | 176.7 (3) | C3—C2—O1—C1 | −1.5 (5) |
C23—C24—C25—C26 | 65.0 (5) | C4—C2—O1—C1 | 180.0 (3) |
Experimental details
Crystal data | |
Chemical formula | C27H35N3O2 |
Mr | 433.58 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 292 |
a, b, c (Å) | 9.4091 (8), 11.4405 (9), 11.9354 (10) |
α, β, γ (°) | 90.080 (2), 94.746 (2), 102.044 (2) |
V (Å3) | 1251.96 (18) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.20 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10980, 4871, 1734 |
Rint | 0.085 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.183, 0.82 |
No. of reflections | 4871 |
No. of parameters | 339 |
No. of restraints | 83 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.16 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL.
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register