Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802022031/cf6225sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802022031/cf62253sup2.hkl |
CCDC reference: 203007
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.005 Å
- R factor = 0.085
- wR factor = 0.287
- Data-to-parameter ratio = 15.1
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level B:
DIFMX_01 Alert B The maximum difference density is > 0.1*ZMAX*1.00 _refine_diff_density_max given = 0.904 Test value = 0.800
Alert Level C:
DIFMX_02 Alert C The minimum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. RFACR_01 Alert C The value of the weighted R factor is > 0.25 Weighted R factor given 0.287 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 30 C6 -C5 -C9 -N2 4.00 0.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 31 C1 -C5 -C9 -N2 16.00 0.00 1.555 1.555 1.555 1.555
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
4 Alert Level C = Please check
Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C18H22N2O | Dx = 1.153 Mg m−3 |
Mr = 282.38 | Melting point = 381.5–383.5 K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.543 (3) Å | Cell parameters from 25 reflections |
b = 10.614 (4) Å | θ = 2–12° |
c = 14.570 (3) Å | µ = 0.07 mm−1 |
β = 93.68 (2)° | T = 295 K |
V = 1627.2 (8) Å3 | Rectangular block, colorless |
Z = 4 | 0.8 × 0.6 × 0.5 mm |
F(000) = 608 |
Enraf-Nonius CAD-4 diffractometer | θmax = 25.0°, θmin = 2.3° |
ω/2θ scans | h = −1→12 |
6534 measured reflections | k = −12→12 |
2863 independent reflections | l = −17→17 |
2336 reflections with I > 2σ(I) | 3 standard reflections every 120 min |
Rint = 0.067 | intensity decay: 3% |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.085 | w = 1/[σ2(Fo2) + (0.1715P)2 + 0.8378P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.287 | (Δ/σ)max = 0.013 |
S = 1.04 | Δρmax = 0.90 e Å−3 |
2863 reflections | Δρmin = −0.38 e Å−3 |
190 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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.2164 (2) | 0.2828 (2) | 0.38453 (16) | 0.0485 (6) | |
C2 | 0.2704 (3) | 0.3378 (3) | 0.29658 (18) | 0.0592 (7) | |
H2A | 0.2577 | 0.4282 | 0.2936 | 0.071* | |
H2B | 0.3606 | 0.3202 | 0.2956 | 0.071* | |
C3 | 0.1978 (4) | 0.2734 (4) | 0.2175 (2) | 0.0822 (10) | |
H3A | 0.1828 | 0.3309 | 0.1662 | 0.099* | |
H3B | 0.2443 | 0.2009 | 0.197 | 0.099* | |
C4 | 0.0761 (4) | 0.2339 (4) | 0.2543 (2) | 0.0854 (11) | |
H4A | 0.0145 | 0.3019 | 0.2502 | 0.102* | |
H4B | 0.0408 | 0.1613 | 0.2213 | 0.102* | |
C5 | 0.1819 (2) | 0.3896 (2) | 0.45188 (19) | 0.0552 (7) | |
H5 | 0.1342 | 0.3516 | 0.5004 | 0.066* | |
C6 | 0.3106 (3) | 0.4340 (3) | 0.4958 (2) | 0.0663 (8) | |
H6 | 0.3476 | 0.4932 | 0.4533 | 0.08* | |
C7 | 0.3884 (3) | 0.3150 (3) | 0.4977 (2) | 0.0705 (9) | |
C8 | 0.3166 (3) | 0.2121 (3) | 0.4469 (2) | 0.0662 (8) | |
H8 | 0.2701 | 0.1663 | 0.4924 | 0.079* | |
C9 | 0.1046 (3) | 0.4897 (3) | 0.4099 (2) | 0.0694 (8) | |
C10 | 0.3062 (4) | 0.4982 (4) | 0.5887 (3) | 0.0988 (13) | |
H10A | 0.3903 | 0.5238 | 0.61 | 0.148* | |
H10B | 0.2733 | 0.4406 | 0.6321 | 0.148* | |
H10C | 0.2521 | 0.5709 | 0.5829 | 0.148* | |
C11 | 0.3990 (5) | 0.1151 (5) | 0.4008 (3) | 0.1150 (17) | |
H11A | 0.4582 | 0.0786 | 0.446 | 0.172* | |
H11B | 0.4447 | 0.1557 | 0.3542 | 0.172* | |
H11C | 0.3458 | 0.0502 | 0.3733 | 0.172* | |
C12 | 0.0052 (3) | 0.1803 (4) | 0.4063 (3) | 0.0825 (10) | |
H12A | −0.0486 | 0.2545 | 0.4051 | 0.099* | |
H12B | 0.0374 | 0.1667 | 0.4694 | 0.099* | |
C13 | −0.0731 (3) | 0.0678 (3) | 0.3740 (2) | 0.0670 (8) | |
C14 | −0.2073 (4) | 0.0809 (3) | 0.3622 (3) | 0.0822 (10) | |
H14 | −0.2453 | 0.1578 | 0.3741 | 0.099* | |
C15 | −0.2815 (3) | −0.0209 (4) | 0.3329 (3) | 0.0837 (10) | |
H15 | −0.3696 | −0.0136 | 0.3265 | 0.1* | |
C16 | −0.2250 (4) | −0.1302 (4) | 0.3138 (3) | 0.0826 (10) | |
H16 | −0.2754 | −0.1977 | 0.2934 | 0.099* | |
C17 | −0.0990 (4) | −0.1458 (4) | 0.3230 (3) | 0.0854 (11) | |
H17 | −0.0625 | −0.2227 | 0.309 | 0.103* | |
C18 | −0.0257 (3) | −0.0480 (3) | 0.3529 (2) | 0.0760 (9) | |
H18 | 0.0618 | −0.0599 | 0.3596 | 0.091* | |
N1 | 0.1116 (2) | 0.2026 (2) | 0.34948 (14) | 0.0513 (6) | |
N2 | 0.0445 (3) | 0.5688 (3) | 0.3777 (3) | 0.1058 (12) | |
O1 | 0.4945 (2) | 0.3060 (3) | 0.5344 (2) | 0.1051 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0490 (13) | 0.0520 (13) | 0.0450 (13) | 0.0070 (10) | 0.0067 (10) | 0.0024 (10) |
C2 | 0.0535 (14) | 0.0706 (17) | 0.0549 (15) | 0.0018 (13) | 0.0146 (11) | 0.0056 (13) |
C3 | 0.106 (3) | 0.095 (2) | 0.0472 (15) | −0.022 (2) | 0.0118 (16) | 0.0103 (15) |
C4 | 0.092 (2) | 0.103 (3) | 0.0591 (18) | −0.020 (2) | −0.0108 (17) | 0.0081 (18) |
C5 | 0.0534 (14) | 0.0557 (15) | 0.0578 (15) | 0.0014 (11) | 0.0123 (11) | −0.0030 (12) |
C6 | 0.0645 (17) | 0.0719 (18) | 0.0627 (16) | −0.0064 (14) | 0.0056 (13) | −0.0088 (14) |
C7 | 0.0626 (17) | 0.095 (2) | 0.0538 (15) | 0.0079 (16) | −0.0021 (13) | 0.0032 (15) |
C8 | 0.0720 (18) | 0.0681 (17) | 0.0574 (16) | 0.0195 (14) | −0.0038 (14) | 0.0039 (13) |
C9 | 0.0622 (17) | 0.0617 (17) | 0.086 (2) | 0.0098 (14) | 0.0163 (15) | −0.0060 (15) |
C10 | 0.111 (3) | 0.107 (3) | 0.078 (2) | −0.013 (2) | 0.005 (2) | −0.036 (2) |
C11 | 0.119 (3) | 0.109 (3) | 0.112 (3) | 0.071 (3) | −0.023 (3) | −0.019 (3) |
C12 | 0.077 (2) | 0.091 (2) | 0.082 (2) | −0.0125 (18) | 0.0216 (17) | −0.0146 (18) |
C13 | 0.0784 (19) | 0.0647 (17) | 0.0604 (16) | −0.0170 (15) | 0.0224 (14) | −0.0022 (13) |
C14 | 0.086 (2) | 0.0650 (18) | 0.097 (3) | 0.0084 (17) | 0.0178 (19) | 0.0006 (17) |
C15 | 0.0594 (18) | 0.088 (2) | 0.104 (3) | −0.0090 (17) | 0.0089 (17) | −0.001 (2) |
C16 | 0.089 (2) | 0.078 (2) | 0.083 (2) | −0.0117 (19) | 0.0256 (18) | 0.0053 (18) |
C17 | 0.113 (3) | 0.067 (2) | 0.079 (2) | 0.010 (2) | 0.025 (2) | 0.0073 (17) |
C18 | 0.076 (2) | 0.083 (2) | 0.0699 (19) | 0.0119 (17) | 0.0169 (15) | 0.0052 (17) |
N1 | 0.0536 (12) | 0.0570 (12) | 0.0439 (11) | −0.0008 (9) | 0.0076 (9) | 0.0052 (9) |
N2 | 0.098 (2) | 0.081 (2) | 0.140 (3) | 0.0355 (19) | 0.021 (2) | 0.016 (2) |
O1 | 0.0753 (16) | 0.141 (3) | 0.0951 (19) | 0.0097 (16) | −0.0264 (14) | −0.0022 (18) |
C1—N1 | 1.461 (3) | C7—C8 | 1.498 (5) |
C1—C8 | 1.543 (4) | C8—C11 | 1.529 (5) |
C1—C2 | 1.550 (3) | C9—N2 | 1.135 (4) |
C1—C5 | 1.558 (3) | C12—N1 | 1.456 (4) |
C2—C3 | 1.506 (4) | C12—C13 | 1.510 (5) |
C3—C4 | 1.482 (5) | C13—C18 | 1.369 (5) |
C4—N1 | 1.452 (4) | C13—C14 | 1.421 (5) |
C5—C9 | 1.450 (4) | C14—C15 | 1.386 (5) |
C5—C6 | 1.537 (4) | C15—C16 | 1.341 (5) |
C6—C7 | 1.505 (5) | C16—C17 | 1.337 (6) |
C6—C10 | 1.520 (5) | C17—C18 | 1.350 (5) |
C7—O1 | 1.212 (4) | ||
N1—C1—C8 | 113.4 (2) | C8—C7—C6 | 110.2 (2) |
N1—C1—C2 | 103.9 (2) | C7—C8—C11 | 115.1 (3) |
C8—C1—C2 | 113.3 (2) | C7—C8—C1 | 104.0 (2) |
N1—C1—C5 | 116.21 (19) | C11—C8—C1 | 117.1 (3) |
C8—C1—C5 | 99.3 (2) | N2—C9—C5 | 179.3 (4) |
C2—C1—C5 | 111.1 (2) | N1—C12—C13 | 112.2 (3) |
C3—C2—C1 | 105.4 (2) | C18—C13—C14 | 115.9 (3) |
C4—C3—C2 | 105.1 (3) | C18—C13—C12 | 125.4 (3) |
N1—C4—C3 | 103.6 (3) | C14—C13—C12 | 118.7 (3) |
C9—C5—C6 | 114.1 (2) | C15—C14—C13 | 119.9 (3) |
C9—C5—C1 | 114.5 (2) | C16—C15—C14 | 119.2 (3) |
C6—C5—C1 | 104.4 (2) | C17—C16—C15 | 122.6 (4) |
C7—C6—C10 | 114.0 (3) | C16—C17—C18 | 118.7 (4) |
C7—C6—C5 | 102.5 (2) | C17—C18—C13 | 123.6 (3) |
C10—C6—C5 | 115.6 (3) | C4—N1—C12 | 114.9 (3) |
O1—C7—C8 | 125.7 (3) | C4—N1—C1 | 110.1 (2) |
O1—C7—C6 | 124.1 (3) | C12—N1—C1 | 119.3 (2) |
N1—C1—C2—C3 | −5.2 (3) | N1—C1—C8—C11 | 69.4 (4) |
C8—C1—C2—C3 | 118.3 (3) | C2—C1—C8—C11 | −48.8 (4) |
C5—C1—C2—C3 | −130.9 (3) | C5—C1—C8—C11 | −166.7 (3) |
C1—C2—C3—C4 | 24.4 (4) | C6—C5—C9—N2 | −4E1 (4) |
C2—C3—C4—N1 | −34.3 (4) | C1—C5—C9—N2 | −16E1 (4) |
N1—C1—C5—C9 | −68.7 (3) | N1—C12—C13—C18 | 47.9 (5) |
C8—C1—C5—C9 | 169.3 (2) | N1—C12—C13—C14 | −130.8 (3) |
C2—C1—C5—C9 | 49.8 (3) | C18—C13—C14—C15 | 1.3 (5) |
N1—C1—C5—C6 | 165.8 (2) | C12—C13—C14—C15 | −179.8 (3) |
C8—C1—C5—C6 | 43.8 (3) | C13—C14—C15—C16 | −1.6 (6) |
C2—C1—C5—C6 | −75.7 (3) | C14—C15—C16—C17 | 0.8 (6) |
C9—C5—C6—C7 | −157.8 (2) | C15—C16—C17—C18 | 0.3 (6) |
C1—C5—C6—C7 | −32.0 (3) | C16—C17—C18—C13 | −0.6 (5) |
C9—C5—C6—C10 | 77.6 (4) | C14—C13—C18—C17 | −0.2 (5) |
C1—C5—C6—C10 | −156.6 (3) | C12—C13—C18—C17 | −179.0 (3) |
C10—C6—C7—O1 | −48.0 (5) | C3—C4—N1—C12 | 170.3 (3) |
C5—C6—C7—O1 | −173.6 (3) | C3—C4—N1—C1 | 32.3 (4) |
C10—C6—C7—C8 | 132.9 (3) | C13—C12—N1—C4 | 63.3 (4) |
C5—C6—C7—C8 | 7.3 (3) | C13—C12—N1—C1 | −162.8 (3) |
O1—C7—C8—C11 | −29.3 (5) | C8—C1—N1—C4 | −140.2 (3) |
C6—C7—C8—C11 | 149.7 (3) | C2—C1—N1—C4 | −16.7 (3) |
O1—C7—C8—C1 | −158.7 (3) | C5—C1—N1—C4 | 105.6 (3) |
C6—C7—C8—C1 | 20.3 (3) | C8—C1—N1—C12 | 83.9 (3) |
N1—C1—C8—C7 | −162.4 (2) | C2—C1—N1—C12 | −152.6 (3) |
C2—C1—C8—C7 | 79.5 (3) | C5—C1—N1—C12 | −30.3 (3) |
C5—C1—C8—C7 | −38.4 (3) |
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