Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803027314/ci6311sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803027314/ci6311IVsup2.hkl |
CCDC reference: 232140
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.044
- wR factor = 0.105
- Data-to-parameter ratio = 16.6
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: 0.840 1.000 Tmin' and Tmax expected: 0.928 0.958 RR' = 0.868 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.87 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96 PLAT480_ALERT_4_C Long H...A H-Bond Reported H12B .. CL1 = 2.91 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.03 From the CIF: _reflns_number_total 3092 Count of symmetry unique reflns 1819 Completeness (_total/calc) 169.98% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1273 Fraction of Friedel pairs measured 0.700 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 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 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1998).
C17H28NO+·Cl− | F(000) = 648 |
Mr = 297.85 | Dx = 1.124 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 827 reflections |
a = 5.882 (2) Å | θ = 3.3–22.8° |
b = 12.187 (5) Å | µ = 0.21 mm−1 |
c = 24.553 (10) Å | T = 293 K |
V = 1760.1 (12) Å3 | Block, colorless |
Z = 4 | 0.34 × 0.32 × 0.20 mm |
Bruker SMART 1000 diffractometer | 2288 reflections with I > 2σ(I) |
ω scans | Rint = 0.033 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | θmax = 25.0°, θmin = 2.4° |
Tmin = 0.841, Tmax = 1.000 | h = −5→7 |
7868 measured reflections | k = −14→13 |
3092 independent reflections | l = −29→14 |
Refinement on F2 | w = 1/[σ2(Fo2) + (0.0567P)2] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.044 | (Δ/σ)max = 0.001 |
wR(F2) = 0.105 | Δρmax = 0.17 e Å−3 |
S = 1.02 | Δρmin = −0.16 e Å−3 |
3092 reflections | Absolute structure: Flack (1983); 1275 Friedel pairs |
186 parameters | Absolute structure parameter: −0.11 (8) |
H-atom parameters constrained |
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. Full-MATRIX |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.67538 (12) | 0.38671 (5) | 0.76206 (3) | 0.0619 (2) | |
N1 | 0.0416 (3) | 0.10464 (15) | 0.73289 (8) | 0.0427 (5) | |
H1 | 0.1204 | 0.0405 | 0.7311 | 0.051* | |
O1 | 0.1507 (3) | −0.04949 (14) | 0.62543 (7) | 0.0561 (5) | |
H1A | 0.1922 | −0.0712 | 0.6554 | 0.084* | |
C1 | 0.2624 (4) | 0.0475 (2) | 0.61293 (10) | 0.0451 (6) | |
C2 | 0.1876 (5) | 0.1429 (2) | 0.63841 (10) | 0.0501 (6) | |
C3 | 0.2985 (5) | 0.2407 (2) | 0.62721 (12) | 0.0632 (8) | |
H3 | 0.2494 | 0.3047 | 0.6441 | 0.076* | |
C4 | 0.4796 (5) | 0.2453 (2) | 0.59167 (12) | 0.0609 (8) | |
C5 | 0.5403 (5) | 0.1493 (2) | 0.56519 (11) | 0.0552 (7) | |
H5 | 0.6569 | 0.1524 | 0.5397 | 0.066* | |
C6 | 0.4373 (4) | 0.0489 (2) | 0.57453 (10) | 0.0437 (6) | |
C7 | −0.0151 (5) | 0.1392 (2) | 0.67555 (11) | 0.0559 (7) | |
H7A | −0.1259 | 0.0885 | 0.6606 | 0.067* | |
H7B | −0.0846 | 0.2114 | 0.6765 | 0.067* | |
C8 | 0.1879 (5) | 0.18707 (18) | 0.76109 (10) | 0.0498 (6) | |
H8A | 0.1092 | 0.2569 | 0.7627 | 0.060* | |
H8B | 0.3273 | 0.1974 | 0.7406 | 0.060* | |
C9 | 0.2442 (5) | 0.1498 (3) | 0.81782 (11) | 0.0677 (9) | |
H9A | 0.3374 | 0.2049 | 0.8356 | 0.081* | |
H9B | 0.3312 | 0.0823 | 0.8161 | 0.081* | |
C10 | 0.0319 (7) | 0.1310 (3) | 0.85084 (13) | 0.0844 (11) | |
H10A | 0.0720 | 0.1042 | 0.8868 | 0.101* | |
H10B | −0.0500 | 0.1996 | 0.8551 | 0.101* | |
C11 | −0.1158 (6) | 0.0486 (3) | 0.82230 (14) | 0.0780 (10) | |
H11A | −0.2560 | 0.0394 | 0.8426 | 0.094* | |
H11B | −0.0385 | −0.0217 | 0.8214 | 0.094* | |
C12 | −0.1715 (4) | 0.0839 (2) | 0.76430 (13) | 0.0592 (7) | |
H12A | −0.2594 | 0.0270 | 0.7465 | 0.071* | |
H12B | −0.2628 | 0.1502 | 0.7651 | 0.071* | |
C13 | 0.6082 (8) | 0.3504 (2) | 0.58199 (16) | 0.0943 (12) | |
H13A | 0.5045 | 0.4064 | 0.5701 | 0.141* | |
H13B | 0.7215 | 0.3387 | 0.5545 | 0.141* | |
H13C | 0.6804 | 0.3731 | 0.6152 | 0.141* | |
C14 | 0.5142 (5) | −0.0558 (2) | 0.54409 (11) | 0.0509 (7) | |
C15 | 0.6119 (5) | −0.1378 (2) | 0.58547 (12) | 0.0654 (8) | |
H15A | 0.6568 | −0.2037 | 0.5669 | 0.098* | |
H15B | 0.4983 | −0.1549 | 0.6122 | 0.098* | |
H15C | 0.7418 | −0.1060 | 0.6031 | 0.098* | |
C16 | 0.3126 (5) | −0.1083 (2) | 0.51392 (11) | 0.0664 (8) | |
H16A | 0.2502 | −0.0564 | 0.4886 | 0.100* | |
H16B | 0.1979 | −0.1291 | 0.5398 | 0.100* | |
H16C | 0.3638 | −0.1721 | 0.4946 | 0.100* | |
C17 | 0.6975 (6) | −0.0308 (3) | 0.50233 (13) | 0.0760 (9) | |
H17A | 0.7412 | −0.0974 | 0.4842 | 0.114* | |
H17B | 0.8273 | 0.0003 | 0.5203 | 0.114* | |
H17C | 0.6398 | 0.0204 | 0.4761 | 0.114* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0646 (4) | 0.0410 (3) | 0.0800 (5) | −0.0074 (3) | −0.0032 (4) | −0.0008 (3) |
N1 | 0.0351 (11) | 0.0367 (10) | 0.0564 (13) | 0.0030 (9) | 0.0010 (10) | −0.0057 (10) |
O1 | 0.0510 (11) | 0.0573 (11) | 0.0599 (11) | −0.0117 (10) | −0.0002 (10) | −0.0092 (10) |
C1 | 0.0438 (15) | 0.0449 (14) | 0.0465 (14) | 0.0021 (12) | −0.0102 (12) | −0.0016 (12) |
C2 | 0.0549 (16) | 0.0486 (15) | 0.0468 (14) | 0.0093 (14) | −0.0023 (14) | −0.0017 (12) |
C3 | 0.082 (2) | 0.0441 (15) | 0.0637 (18) | 0.0150 (16) | −0.0036 (19) | 0.0003 (13) |
C4 | 0.075 (2) | 0.0465 (16) | 0.0612 (18) | −0.0002 (16) | −0.0067 (18) | 0.0110 (14) |
C5 | 0.0526 (17) | 0.0613 (18) | 0.0518 (15) | 0.0011 (14) | 0.0019 (14) | 0.0116 (14) |
C6 | 0.0418 (14) | 0.0481 (15) | 0.0412 (14) | 0.0058 (12) | −0.0045 (12) | −0.0005 (12) |
C7 | 0.0480 (16) | 0.0648 (18) | 0.0548 (16) | 0.0143 (14) | −0.0064 (14) | −0.0095 (14) |
C8 | 0.0487 (14) | 0.0427 (13) | 0.0580 (15) | −0.0064 (12) | 0.0038 (16) | −0.0068 (12) |
C9 | 0.069 (2) | 0.079 (2) | 0.0548 (17) | −0.0063 (16) | −0.0068 (16) | −0.0108 (15) |
C10 | 0.097 (3) | 0.098 (3) | 0.0581 (19) | 0.006 (2) | 0.011 (2) | 0.0047 (19) |
C11 | 0.064 (2) | 0.081 (2) | 0.090 (2) | 0.0074 (19) | 0.0260 (18) | 0.032 (2) |
C12 | 0.0355 (14) | 0.0537 (15) | 0.089 (2) | −0.0017 (13) | 0.0097 (17) | 0.0049 (15) |
C13 | 0.116 (3) | 0.0552 (18) | 0.112 (3) | −0.0128 (19) | 0.006 (2) | 0.0209 (19) |
C14 | 0.0469 (15) | 0.0580 (16) | 0.0477 (15) | 0.0053 (14) | −0.0022 (13) | −0.0067 (13) |
C15 | 0.0618 (19) | 0.0656 (19) | 0.0687 (19) | 0.0218 (15) | −0.0073 (15) | −0.0084 (15) |
C16 | 0.0648 (18) | 0.0756 (18) | 0.0588 (17) | 0.0082 (19) | −0.0110 (16) | −0.0234 (16) |
C17 | 0.069 (2) | 0.086 (2) | 0.073 (2) | 0.013 (2) | 0.0170 (19) | −0.0082 (17) |
N1—C8 | 1.493 (3) | C9—H9B | 0.97 |
N1—C12 | 1.493 (3) | C10—C11 | 1.502 (5) |
N1—C7 | 1.507 (3) | C10—H10A | 0.97 |
N1—H1 | 0.91 | C10—H10B | 0.97 |
O1—C1 | 1.387 (3) | C11—C12 | 1.523 (4) |
O1—H1A | 0.82 | C11—H11A | 0.97 |
C1—C2 | 1.391 (3) | C11—H11B | 0.97 |
C1—C6 | 1.395 (3) | C12—H12A | 0.97 |
C2—C3 | 1.386 (4) | C12—H12B | 0.97 |
C2—C7 | 1.501 (4) | C13—H13A | 0.96 |
C3—C4 | 1.378 (4) | C13—H13B | 0.96 |
C3—H3 | 0.93 | C13—H13C | 0.96 |
C4—C5 | 1.386 (4) | C14—C17 | 1.518 (4) |
C4—C13 | 1.507 (4) | C14—C15 | 1.536 (4) |
C5—C6 | 1.384 (4) | C14—C16 | 1.538 (4) |
C5—H5 | 0.93 | C15—H15A | 0.96 |
C6—C14 | 1.546 (4) | C15—H15B | 0.96 |
C7—H7A | 0.97 | C15—H15C | 0.96 |
C7—H7B | 0.97 | C16—H16A | 0.96 |
C8—C9 | 1.502 (4) | C16—H16B | 0.96 |
C8—H8A | 0.97 | C16—H16C | 0.96 |
C8—H8B | 0.97 | C17—H17A | 0.96 |
C9—C10 | 1.506 (5) | C17—H17B | 0.96 |
C9—H9A | 0.97 | C17—H17C | 0.96 |
C8—N1—C12 | 110.98 (19) | C11—C10—H10B | 109.8 |
C8—N1—C7 | 111.88 (19) | C9—C10—H10B | 109.8 |
C12—N1—C7 | 110.1 (2) | H10A—C10—H10B | 108.3 |
C8—N1—H1 | 107.9 | C10—C11—C12 | 111.8 (3) |
C12—N1—H1 | 107.9 | C10—C11—H11A | 109.3 |
C7—N1—H1 | 107.9 | C12—C11—H11A | 109.3 |
C1—O1—H1A | 109.5 | C10—C11—H11B | 109.3 |
O1—C1—C2 | 117.6 (2) | C12—C11—H11B | 109.3 |
O1—C1—C6 | 120.6 (2) | H11A—C11—H11B | 107.9 |
C2—C1—C6 | 121.8 (2) | N1—C12—C11 | 110.5 (2) |
C3—C2—C1 | 118.7 (3) | N1—C12—H12A | 109.6 |
C3—C2—C7 | 121.3 (2) | C11—C12—H12A | 109.6 |
C1—C2—C7 | 120.0 (2) | N1—C12—H12B | 109.6 |
C4—C3—C2 | 121.6 (3) | C11—C12—H12B | 109.6 |
C4—C3—H3 | 119.2 | H12A—C12—H12B | 108.1 |
C2—C3—H3 | 119.2 | C4—C13—H13A | 109.5 |
C3—C4—C5 | 117.5 (3) | C4—C13—H13B | 109.5 |
C3—C4—C13 | 121.5 (3) | H13A—C13—H13B | 109.5 |
C5—C4—C13 | 121.0 (3) | C4—C13—H13C | 109.5 |
C6—C5—C4 | 123.8 (3) | H13A—C13—H13C | 109.5 |
C6—C5—H5 | 118.1 | H13B—C13—H13C | 109.5 |
C4—C5—H5 | 118.1 | C17—C14—C15 | 108.1 (2) |
C5—C6—C1 | 116.4 (2) | C17—C14—C16 | 107.8 (2) |
C5—C6—C14 | 121.4 (2) | C15—C14—C16 | 109.7 (2) |
C1—C6—C14 | 122.2 (2) | C17—C14—C6 | 111.6 (2) |
C2—C7—N1 | 113.6 (2) | C15—C14—C6 | 109.0 (2) |
C2—C7—H7A | 108.8 | C16—C14—C6 | 110.5 (2) |
N1—C7—H7A | 108.8 | C14—C15—H15A | 109.5 |
C2—C7—H7B | 108.8 | C14—C15—H15B | 109.5 |
N1—C7—H7B | 108.8 | H15A—C15—H15B | 109.5 |
H7A—C7—H7B | 107.7 | C14—C15—H15C | 109.5 |
N1—C8—C9 | 110.7 (2) | H15A—C15—H15C | 109.5 |
N1—C8—H8A | 109.5 | H15B—C15—H15C | 109.5 |
C9—C8—H8A | 109.5 | C14—C16—H16A | 109.5 |
N1—C8—H8B | 109.5 | C14—C16—H16B | 109.5 |
C9—C8—H8B | 109.5 | H16A—C16—H16B | 109.5 |
H8A—C8—H8B | 108.1 | C14—C16—H16C | 109.5 |
C8—C9—C10 | 111.2 (3) | H16A—C16—H16C | 109.5 |
C8—C9—H9A | 109.4 | H16B—C16—H16C | 109.5 |
C10—C9—H9A | 109.4 | C14—C17—H17A | 109.5 |
C8—C9—H9B | 109.4 | C14—C17—H17B | 109.5 |
C10—C9—H9B | 109.4 | H17A—C17—H17B | 109.5 |
H9A—C9—H9B | 108.0 | C14—C17—H17C | 109.5 |
C11—C10—C9 | 109.3 (3) | H17A—C17—H17C | 109.5 |
C11—C10—H10A | 109.8 | H17B—C17—H17C | 109.5 |
C9—C10—H10A | 109.8 | ||
O1—C1—C2—C3 | 179.1 (2) | C1—C2—C7—N1 | 84.0 (3) |
C6—C1—C2—C3 | −3.4 (4) | C8—N1—C7—C2 | 66.1 (3) |
O1—C1—C2—C7 | −3.2 (3) | C12—N1—C7—C2 | −170.0 (2) |
C6—C1—C2—C7 | 174.3 (2) | C12—N1—C8—C9 | 57.3 (3) |
C1—C2—C3—C4 | 0.0 (4) | C7—N1—C8—C9 | −179.2 (2) |
C7—C2—C3—C4 | −177.7 (3) | N1—C8—C9—C10 | −58.3 (3) |
C2—C3—C4—C5 | 3.2 (4) | C8—C9—C10—C11 | 57.1 (4) |
C2—C3—C4—C13 | −176.5 (3) | C9—C10—C11—C12 | −56.0 (4) |
C3—C4—C5—C6 | −3.4 (4) | C8—N1—C12—C11 | −55.7 (3) |
C13—C4—C5—C6 | 176.3 (3) | C7—N1—C12—C11 | 179.8 (2) |
C4—C5—C6—C1 | 0.3 (4) | C10—C11—C12—N1 | 55.9 (3) |
C4—C5—C6—C14 | −179.4 (3) | C5—C6—C14—C17 | −3.7 (3) |
O1—C1—C6—C5 | −179.3 (2) | C1—C6—C14—C17 | 176.7 (2) |
C2—C1—C6—C5 | 3.2 (3) | C5—C6—C14—C15 | 115.8 (3) |
O1—C1—C6—C14 | 0.3 (3) | C1—C6—C14—C15 | −63.9 (3) |
C2—C1—C6—C14 | −177.2 (2) | C5—C6—C14—C16 | −123.6 (3) |
C3—C2—C7—N1 | −98.4 (3) | C1—C6—C14—C16 | 56.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Cl1i | 0.91 | 2.23 | 3.137 (3) | 173 |
O1—H1A···Cl1i | 0.82 | 2.23 | 3.047 (3) | 174 |
C12—H12B···Cl1ii | 0.97 | 2.91 | 3.799 (4) | 153 |
C15—H15C···O1iii | 0.96 | 2.56 | 3.487 (3) | 162 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x−1, y, z; (iii) x+1, y, z. |
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