Two fluorine-substituted 1,4,5,6-tetrahydrobenzo[h]quinazolin-2-amine (BQA) derivatives, namely 2-amino-4-(2-fluorophenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, (8), and 2-amino-4-(4-fluorophenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, (9), both C19H19FN3O+·Cl−, were generated by Michael addition reactions between guanidine hydrochloride and the α,β-unsaturated ketones (E)-2-(2-fluorobenzylidene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, C18H15FO2, (6), and (E)-2-(4-fluorobenzylidene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, (7). Because both sides of α,β-unsaturated ketones (6) or (7) can be attacked by guanidine, we obtained a pair of isomers in (8) and (9). Single-crystal X-ray diffraction indicates that each isomer has a chiral C atom and both (8) and (9) crystallize in the achiral space group P21/c. The chloride ion, as a hydrogen-bond acceptor, plays an important role in the formation of multiple hydrogen bonds. Thus, adjacent molecules are connected through intermolecular hydrogen bonds to generate a banded structure. Furthermore, these bands are linked into an interesting 3D network via hydrogen bonds and π–π interactions. Fortunately, the solubilities of (8) and (9) were distinctly improved and can exceed 50 mg ml−1 in water or PBS buffer system (pH 7.4) at room temperature. In addition, the results of an investigation of anti-inflammatory activity show that (8) and (9), with o- and p-fluoro substituents, respectively, display more potential for inhibitory effects on LPS-induced NO secretion than starting ketones (6) and (7).
Supporting information
CCDC references: 1938473; 1938474; 1938475
For all structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for 2-F; SHELXT2017 (Sheldrick, 2015a) for (2F), 4HF. For all structures, program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
(
E)-2-(2-Fluorobenzylidene)-7-methoxy-3,4-dihydronaphthalen-1(2
H)-one (2-F)
top
Crystal data top
C18H15FO2 | Z = 2 |
Mr = 282.30 | F(000) = 296 |
Triclinic, P1 | Dx = 1.407 Mg m−3 |
a = 7.3336 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.9301 (7) Å | Cell parameters from 3078 reflections |
c = 12.5780 (12) Å | θ = 2.9–28.8° |
α = 107.140 (8)° | µ = 0.10 mm−1 |
β = 104.982 (7)° | T = 100 K |
γ = 94.285 (7)° | Block, colourless |
V = 666.16 (11) Å3 | 0.14 × 0.13 × 0.11 mm |
Data collection top
Rigaku OD SuperNova Dual source diffractometer with an AtlasS2 detector | 2483 independent reflections |
Radiation source: micro-focus sealed X-ray tube | 2111 reflections with I > 2σ(I) |
Detector resolution: 5.2684 pixels mm-1 | Rint = 0.027 |
CCD plate scans | θmax = 25.5°, θmin = 2.7° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | h = −8→8 |
Tmin = 0.434, Tmax = 1.000 | k = −9→9 |
4966 measured reflections | l = −12→15 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.046P)2 + 0.1085P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
2483 reflections | Δρmax = 0.20 e Å−3 |
191 parameters | Δρmin = −0.26 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.7219 (2) | 0.36064 (18) | 0.51141 (12) | 0.0160 (3) | |
H1 | 0.771228 | 0.397728 | 0.459412 | 0.019* | |
C2 | 0.8376 (2) | 0.38741 (18) | 0.62270 (12) | 0.0159 (3) | |
C3 | 0.7621 (2) | 0.3348 (2) | 0.70103 (13) | 0.0190 (3) | |
H3 | 0.838697 | 0.353096 | 0.776307 | 0.023* | |
C4 | 0.5723 (2) | 0.25518 (19) | 0.66611 (13) | 0.0193 (3) | |
H4 | 0.522910 | 0.221566 | 0.719243 | 0.023* | |
C5 | 0.2523 (2) | 0.12430 (19) | 0.51545 (12) | 0.0177 (3) | |
H5A | 0.198841 | 0.156389 | 0.580286 | 0.021* | |
H5B | 0.255855 | −0.003073 | 0.494067 | 0.021* | |
C6 | 0.1213 (2) | 0.1631 (2) | 0.41247 (12) | 0.0177 (3) | |
H6A | 0.003819 | 0.077116 | 0.381316 | 0.021* | |
H6B | 0.088339 | 0.281330 | 0.439371 | 0.021* | |
C7 | 0.2127 (2) | 0.15410 (19) | 0.31732 (12) | 0.0166 (3) | |
C8 | 0.4169 (2) | 0.24318 (19) | 0.35363 (12) | 0.0172 (3) | |
C9 | 0.5314 (2) | 0.27827 (18) | 0.47650 (12) | 0.0149 (3) | |
C10 | 0.4534 (2) | 0.22389 (18) | 0.55411 (12) | 0.0164 (3) | |
C11 | 0.1335 (2) | 0.0673 (2) | 0.20364 (13) | 0.0187 (3) | |
H11 | 0.209750 | 0.074230 | 0.155901 | 0.022* | |
C12 | −0.0593 (2) | −0.0379 (2) | 0.14472 (12) | 0.0185 (3) | |
C13 | −0.0863 (2) | −0.1965 (2) | 0.05371 (13) | 0.0223 (4) | |
C14 | −0.2605 (2) | −0.3018 (2) | −0.00726 (13) | 0.0284 (4) | |
H14 | −0.270830 | −0.407259 | −0.067319 | 0.034* | |
C15 | −0.4207 (2) | −0.2480 (2) | 0.02229 (13) | 0.0288 (4) | |
H15 | −0.540278 | −0.318152 | −0.017339 | 0.035* | |
C16 | −0.4029 (2) | −0.0899 (2) | 0.11074 (13) | 0.0249 (4) | |
H16 | −0.511128 | −0.052936 | 0.129795 | 0.030* | |
C17 | −0.2249 (2) | 0.0139 (2) | 0.17129 (13) | 0.0215 (4) | |
H17 | −0.215211 | 0.120052 | 0.230704 | 0.026* | |
C18 | 1.1507 (2) | 0.4830 (2) | 0.75923 (13) | 0.0237 (4) | |
H18A | 1.107737 | 0.560376 | 0.819054 | 0.036* | |
H18B | 1.277251 | 0.533148 | 0.764463 | 0.036* | |
H18C | 1.152546 | 0.367514 | 0.769061 | 0.036* | |
F1 | 0.07165 (13) | −0.25142 (13) | 0.02496 (8) | 0.0327 (3) | |
O1 | 1.02370 (14) | 0.46497 (13) | 0.64784 (8) | 0.0189 (3) | |
O2 | 0.48946 (15) | 0.27890 (15) | 0.28387 (9) | 0.0244 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0173 (8) | 0.0128 (7) | 0.0207 (7) | 0.0034 (6) | 0.0092 (6) | 0.0061 (6) |
C2 | 0.0139 (7) | 0.0124 (7) | 0.0215 (7) | 0.0020 (6) | 0.0072 (6) | 0.0040 (6) |
C3 | 0.0192 (8) | 0.0199 (8) | 0.0172 (7) | 0.0036 (6) | 0.0042 (6) | 0.0058 (6) |
C4 | 0.0222 (8) | 0.0188 (8) | 0.0217 (8) | 0.0039 (6) | 0.0124 (6) | 0.0082 (6) |
C5 | 0.0182 (8) | 0.0165 (7) | 0.0221 (8) | 0.0027 (6) | 0.0118 (6) | 0.0067 (6) |
C6 | 0.0130 (7) | 0.0180 (8) | 0.0214 (8) | −0.0002 (6) | 0.0069 (6) | 0.0047 (6) |
C7 | 0.0151 (8) | 0.0155 (7) | 0.0218 (8) | 0.0037 (6) | 0.0067 (6) | 0.0084 (6) |
C8 | 0.0173 (8) | 0.0151 (7) | 0.0218 (8) | 0.0048 (6) | 0.0090 (6) | 0.0065 (6) |
C9 | 0.0151 (7) | 0.0118 (7) | 0.0197 (7) | 0.0044 (6) | 0.0083 (6) | 0.0046 (6) |
C10 | 0.0159 (8) | 0.0132 (7) | 0.0222 (7) | 0.0047 (6) | 0.0091 (6) | 0.0055 (6) |
C11 | 0.0164 (8) | 0.0210 (8) | 0.0224 (8) | 0.0043 (6) | 0.0081 (6) | 0.0102 (6) |
C12 | 0.0175 (8) | 0.0216 (8) | 0.0187 (7) | 0.0031 (6) | 0.0049 (6) | 0.0102 (6) |
C13 | 0.0219 (9) | 0.0285 (9) | 0.0189 (8) | 0.0049 (7) | 0.0076 (6) | 0.0097 (7) |
C14 | 0.0316 (10) | 0.0290 (9) | 0.0177 (8) | −0.0037 (7) | 0.0032 (7) | 0.0032 (7) |
C15 | 0.0200 (9) | 0.0374 (10) | 0.0237 (8) | −0.0072 (7) | −0.0020 (7) | 0.0127 (8) |
C16 | 0.0154 (8) | 0.0357 (10) | 0.0258 (8) | 0.0038 (7) | 0.0046 (7) | 0.0146 (7) |
C17 | 0.0197 (8) | 0.0224 (8) | 0.0235 (8) | 0.0038 (6) | 0.0052 (7) | 0.0099 (7) |
C18 | 0.0159 (8) | 0.0309 (9) | 0.0201 (8) | −0.0015 (7) | 0.0011 (6) | 0.0072 (7) |
F1 | 0.0287 (6) | 0.0381 (6) | 0.0277 (5) | 0.0066 (4) | 0.0133 (4) | 0.0010 (4) |
O1 | 0.0128 (5) | 0.0234 (6) | 0.0196 (5) | −0.0010 (4) | 0.0032 (4) | 0.0079 (4) |
O2 | 0.0188 (6) | 0.0348 (7) | 0.0208 (6) | −0.0032 (5) | 0.0071 (5) | 0.0112 (5) |
Geometric parameters (Å, º) top
C1—C2 | 1.381 (2) | C8—C9 | 1.487 (2) |
C1—C9 | 1.396 (2) | C9—C10 | 1.402 (2) |
C1—H1 | 0.9300 | C11—C12 | 1.470 (2) |
C2—O1 | 1.3704 (17) | C11—H11 | 0.9300 |
C2—C3 | 1.393 (2) | C12—C13 | 1.389 (2) |
C3—C4 | 1.385 (2) | C12—C17 | 1.399 (2) |
C3—H3 | 0.9300 | C13—F1 | 1.3642 (18) |
C4—C10 | 1.391 (2) | C13—C14 | 1.369 (2) |
C4—H4 | 0.9300 | C14—C15 | 1.381 (2) |
C5—C10 | 1.5048 (19) | C14—H14 | 0.9300 |
C5—C6 | 1.527 (2) | C15—C16 | 1.380 (2) |
C5—H5A | 0.9700 | C15—H15 | 0.9300 |
C5—H5B | 0.9700 | C16—C17 | 1.385 (2) |
C6—C7 | 1.5030 (19) | C16—H16 | 0.9300 |
C6—H6A | 0.9700 | C17—H17 | 0.9300 |
C6—H6B | 0.9700 | C18—O1 | 1.4277 (17) |
C7—C11 | 1.337 (2) | C18—H18A | 0.9600 |
C7—C8 | 1.499 (2) | C18—H18B | 0.9600 |
C8—O2 | 1.2243 (17) | C18—H18C | 0.9600 |
| | | |
C2—C1—C9 | 120.41 (13) | C10—C9—C8 | 121.19 (13) |
C2—C1—H1 | 119.8 | C4—C10—C9 | 117.60 (13) |
C9—C1—H1 | 119.8 | C4—C10—C5 | 121.03 (13) |
O1—C2—C1 | 116.13 (12) | C9—C10—C5 | 121.24 (13) |
O1—C2—C3 | 124.25 (13) | C7—C11—C12 | 128.04 (14) |
C1—C2—C3 | 119.62 (13) | C7—C11—H11 | 116.0 |
C4—C3—C2 | 119.58 (13) | C12—C11—H11 | 116.0 |
C4—C3—H3 | 120.2 | C13—C12—C17 | 115.84 (14) |
C2—C3—H3 | 120.2 | C13—C12—C11 | 119.95 (14) |
C3—C4—C10 | 122.07 (14) | C17—C12—C11 | 124.17 (13) |
C3—C4—H4 | 119.0 | F1—C13—C14 | 118.31 (14) |
C10—C4—H4 | 119.0 | F1—C13—C12 | 117.63 (13) |
C10—C5—C6 | 113.30 (12) | C14—C13—C12 | 124.05 (15) |
C10—C5—H5A | 108.9 | C13—C14—C15 | 118.61 (15) |
C6—C5—H5A | 108.9 | C13—C14—H14 | 120.7 |
C10—C5—H5B | 108.9 | C15—C14—H14 | 120.7 |
C6—C5—H5B | 108.9 | C16—C15—C14 | 119.87 (15) |
H5A—C5—H5B | 107.7 | C16—C15—H15 | 120.1 |
C7—C6—C5 | 112.34 (12) | C14—C15—H15 | 120.1 |
C7—C6—H6A | 109.1 | C15—C16—C17 | 120.38 (15) |
C5—C6—H6A | 109.1 | C15—C16—H16 | 119.8 |
C7—C6—H6B | 109.1 | C17—C16—H16 | 119.8 |
C5—C6—H6B | 109.1 | C16—C17—C12 | 121.22 (14) |
H6A—C6—H6B | 107.9 | C16—C17—H17 | 119.4 |
C11—C7—C8 | 116.35 (13) | C12—C17—H17 | 119.4 |
C11—C7—C6 | 126.58 (13) | O1—C18—H18A | 109.5 |
C8—C7—C6 | 116.99 (12) | O1—C18—H18B | 109.5 |
O2—C8—C9 | 121.03 (13) | H18A—C18—H18B | 109.5 |
O2—C8—C7 | 121.45 (13) | O1—C18—H18C | 109.5 |
C9—C8—C7 | 117.45 (12) | H18A—C18—H18C | 109.5 |
C1—C9—C10 | 120.70 (13) | H18B—C18—H18C | 109.5 |
C1—C9—C8 | 118.05 (13) | C2—O1—C18 | 117.62 (11) |
| | | |
C9—C1—C2—O1 | 178.32 (12) | C1—C9—C10—C5 | −175.98 (13) |
C9—C1—C2—C3 | −1.2 (2) | C8—C9—C10—C5 | 1.4 (2) |
O1—C2—C3—C4 | −179.08 (13) | C6—C5—C10—C4 | 157.80 (13) |
C1—C2—C3—C4 | 0.5 (2) | C6—C5—C10—C9 | −26.33 (19) |
C2—C3—C4—C10 | 0.6 (2) | C8—C7—C11—C12 | 176.97 (14) |
C10—C5—C6—C7 | 46.60 (17) | C6—C7—C11—C12 | 0.4 (3) |
C5—C6—C7—C11 | 132.15 (15) | C7—C11—C12—C13 | −140.31 (16) |
C5—C6—C7—C8 | −44.41 (17) | C7—C11—C12—C17 | 42.1 (2) |
C11—C7—C8—O2 | 20.0 (2) | C17—C12—C13—F1 | 179.87 (13) |
C6—C7—C8—O2 | −163.05 (14) | C11—C12—C13—F1 | 2.1 (2) |
C11—C7—C8—C9 | −156.89 (13) | C17—C12—C13—C14 | −1.2 (2) |
C6—C7—C8—C9 | 20.02 (18) | C11—C12—C13—C14 | −179.02 (14) |
C2—C1—C9—C10 | 1.0 (2) | F1—C13—C14—C15 | 179.26 (14) |
C2—C1—C9—C8 | −176.44 (12) | C12—C13—C14—C15 | 0.3 (2) |
O2—C8—C9—C1 | 2.9 (2) | C13—C14—C15—C16 | 0.8 (2) |
C7—C8—C9—C1 | 179.80 (12) | C14—C15—C16—C17 | −1.0 (2) |
O2—C8—C9—C10 | −174.57 (13) | C15—C16—C17—C12 | 0.0 (2) |
C7—C8—C9—C10 | 2.4 (2) | C13—C12—C17—C16 | 1.0 (2) |
C3—C4—C10—C9 | −0.8 (2) | C11—C12—C17—C16 | 178.71 (13) |
C3—C4—C10—C5 | 175.18 (13) | C1—C2—O1—C18 | −175.63 (12) |
C1—C9—C10—C4 | 0.0 (2) | C3—C2—O1—C18 | 3.9 (2) |
C8—C9—C10—C4 | 177.40 (12) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18B···O2i | 0.96 | 2.49 | 3.3795 (19) | 154 |
C1—H1···O1i | 0.93 | 2.63 | 3.5475 (18) | 168 |
Symmetry code: (i) −x+2, −y+1, −z+1. |
2-Amino-4-(2-fluorophenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[
h]quinazolin-3-ium chloride (2F)
top
Crystal data top
C19H19FN3O+·Cl− | F(000) = 1504 |
Mr = 359.82 | Dx = 1.390 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 17.1415 (7) Å | Cell parameters from 6100 reflections |
b = 11.7917 (4) Å | θ = 2.5–29.3° |
c = 17.3364 (7) Å | µ = 0.25 mm−1 |
β = 101.165 (4)° | T = 100 K |
V = 3437.8 (2) Å3 | Block, colourless |
Z = 8 | 0.12 × 0.11 × 0.10 mm |
Data collection top
Rigaku OD SuperNova Dual source diffractometer with an AtlasS2 detector | 6394 independent reflections |
Radiation source: micro-focus sealed X-ray tube | 5203 reflections with I > 2σ(I) |
Detector resolution: 5.2684 pixels mm-1 | Rint = 0.032 |
CCD plate scans | θmax = 25.5°, θmin = 2.1° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | h = −20→15 |
Tmin = 0.920, Tmax = 1.000 | k = −14→12 |
16601 measured reflections | l = −21→20 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.102 | w = 1/[σ2(Fo2) + (0.0392P)2 + 1.8116P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
6394 reflections | Δρmax = 0.60 e Å−3 |
453 parameters | Δρmin = −0.28 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.77318 (12) | 0.68934 (17) | 0.87615 (12) | 0.0197 (5) | |
H1 | 0.822058 | 0.665648 | 0.866287 | 0.024* | |
C2 | 0.72156 (12) | 0.61056 (17) | 0.89837 (12) | 0.0198 (5) | |
C3 | 0.64969 (13) | 0.64515 (19) | 0.91558 (12) | 0.0236 (5) | |
H3 | 0.615754 | 0.593103 | 0.932339 | 0.028* | |
C4 | 0.62915 (13) | 0.75944 (18) | 0.90730 (12) | 0.0232 (5) | |
H4 | 0.580599 | 0.782682 | 0.918238 | 0.028* | |
C5 | 0.65264 (13) | 0.96060 (18) | 0.86533 (13) | 0.0252 (5) | |
H5A | 0.613909 | 0.981150 | 0.896951 | 0.030* | |
H5B | 0.626756 | 0.965871 | 0.810505 | 0.030* | |
C6 | 0.72072 (13) | 1.04455 (18) | 0.88095 (13) | 0.0237 (5) | |
H6A | 0.703336 | 1.116648 | 0.856616 | 0.028* | |
H6B | 0.736690 | 1.056702 | 0.937131 | 0.028* | |
C7 | 0.79053 (12) | 1.00131 (17) | 0.84858 (11) | 0.0175 (4) | |
C8 | 0.80470 (11) | 0.89048 (17) | 0.84464 (11) | 0.0153 (4) | |
C9 | 0.75244 (12) | 0.80355 (17) | 0.86850 (11) | 0.0163 (4) | |
C10 | 0.67840 (12) | 0.83951 (17) | 0.88340 (11) | 0.0183 (5) | |
C11 | 0.84269 (12) | 1.08906 (17) | 0.82115 (12) | 0.0188 (5) | |
H11 | 0.810265 | 1.131345 | 0.777813 | 0.023* | |
C12 | 0.92182 (12) | 0.92333 (16) | 0.79180 (11) | 0.0152 (4) | |
C13 | 0.87880 (12) | 1.17351 (17) | 0.88404 (11) | 0.0171 (4) | |
C14 | 0.88441 (13) | 1.28725 (18) | 0.86723 (12) | 0.0205 (5) | |
C15 | 0.92037 (13) | 1.36660 (18) | 0.92082 (13) | 0.0241 (5) | |
H15 | 0.922498 | 1.442551 | 0.906908 | 0.029* | |
C16 | 0.95314 (12) | 1.33021 (19) | 0.99574 (13) | 0.0236 (5) | |
H16 | 0.978218 | 1.381891 | 1.032952 | 0.028* | |
C17 | 0.94881 (14) | 1.21712 (19) | 1.01567 (13) | 0.0278 (5) | |
H17 | 0.970606 | 1.193086 | 1.066357 | 0.033* | |
C18 | 0.91214 (14) | 1.13964 (18) | 0.96039 (13) | 0.0255 (5) | |
H18 | 0.909683 | 1.063769 | 0.974375 | 0.031* | |
C19 | 0.69762 (13) | 0.41609 (18) | 0.92465 (13) | 0.0267 (5) | |
H19A | 0.689195 | 0.433220 | 0.976552 | 0.040* | |
H19B | 0.722416 | 0.343067 | 0.924789 | 0.040* | |
H19C | 0.647455 | 0.415299 | 0.888629 | 0.040* | |
C1A | 0.72808 (12) | 0.87082 (16) | 0.64295 (11) | 0.0156 (4) | |
H1B | 0.683683 | 0.892306 | 0.662887 | 0.019* | |
C2A | 0.77900 (12) | 0.95314 (16) | 0.62342 (11) | 0.0171 (4) | |
C3A | 0.84551 (13) | 0.92214 (17) | 0.59422 (12) | 0.0205 (5) | |
H3A | 0.879949 | 0.977038 | 0.581655 | 0.025* | |
C4A | 0.86009 (13) | 0.80776 (18) | 0.58395 (12) | 0.0217 (5) | |
H4A | 0.904591 | 0.786989 | 0.563925 | 0.026* | |
C5A | 0.82410 (13) | 0.60003 (17) | 0.58813 (13) | 0.0225 (5) | |
H5A1 | 0.880318 | 0.587741 | 0.589567 | 0.027* | |
H5A2 | 0.795591 | 0.579814 | 0.536021 | 0.027* | |
C6A | 0.79705 (12) | 0.52306 (17) | 0.64831 (12) | 0.0199 (5) | |
H6A1 | 0.794683 | 0.445421 | 0.629513 | 0.024* | |
H6A2 | 0.835513 | 0.526316 | 0.697308 | 0.024* | |
C7A | 0.71688 (12) | 0.55736 (16) | 0.66291 (11) | 0.0156 (4) | |
C8A | 0.69295 (11) | 0.66559 (16) | 0.65483 (11) | 0.0139 (4) | |
C9A | 0.74323 (11) | 0.75667 (16) | 0.63281 (11) | 0.0149 (4) | |
C10A | 0.81041 (12) | 0.72371 (17) | 0.60261 (11) | 0.0172 (4) | |
C11A | 0.66786 (12) | 0.46817 (16) | 0.69303 (11) | 0.0156 (4) | |
H11A | 0.702632 | 0.427119 | 0.735434 | 0.019* | |
C12A | 0.57782 (12) | 0.62533 (17) | 0.70959 (11) | 0.0153 (4) | |
C13A | 0.63176 (12) | 0.38173 (16) | 0.63043 (11) | 0.0152 (4) | |
C14A | 0.62156 (12) | 0.26950 (17) | 0.64953 (11) | 0.0176 (4) | |
C15A | 0.58783 (12) | 0.18847 (17) | 0.59644 (12) | 0.0201 (5) | |
H15A | 0.582958 | 0.113709 | 0.611933 | 0.024* | |
C16A | 0.56140 (12) | 0.22144 (18) | 0.51938 (12) | 0.0217 (5) | |
H16A | 0.537891 | 0.168657 | 0.482179 | 0.026* | |
C17A | 0.56983 (14) | 0.33282 (19) | 0.49746 (13) | 0.0269 (5) | |
H17A | 0.551799 | 0.354816 | 0.445549 | 0.032* | |
C18A | 0.60494 (13) | 0.41159 (18) | 0.55236 (12) | 0.0234 (5) | |
H18A | 0.610722 | 0.486051 | 0.536698 | 0.028* | |
C19A | 0.80734 (13) | 1.15122 (17) | 0.61430 (13) | 0.0229 (5) | |
H19D | 0.860523 | 1.143334 | 0.643874 | 0.034* | |
H19E | 0.786463 | 1.223793 | 0.625118 | 0.034* | |
H19F | 0.807905 | 1.145484 | 0.559170 | 0.034* | |
Cl1 | 0.96307 (3) | 0.62076 (4) | 0.80113 (3) | 0.01843 (13) | |
Cl1A | 0.51642 (3) | 0.92160 (4) | 0.67382 (3) | 0.01800 (13) | |
F1 | 0.85466 (8) | 1.32268 (10) | 0.79223 (7) | 0.0348 (3) | |
F1A | 0.64645 (8) | 0.23764 (10) | 0.72615 (7) | 0.0288 (3) | |
N1 | 0.87236 (10) | 0.85180 (13) | 0.81748 (10) | 0.0169 (4) | |
H1A | 0.881602 | 0.783543 | 0.812344 | 0.025* | |
N2 | 0.90769 (10) | 1.03351 (14) | 0.79089 (10) | 0.0191 (4) | |
H2A | 0.940904 | 1.073117 | 0.774138 | 0.029* | |
N3 | 0.98608 (10) | 0.88383 (14) | 0.76880 (10) | 0.0191 (4) | |
H3B | 0.990159 | 0.814864 | 0.765967 | 0.029* | |
H3C | 1.012553 | 0.927153 | 0.745400 | 0.029* | |
N1A | 0.61863 (10) | 0.69642 (13) | 0.67234 (9) | 0.0164 (4) | |
H1AA | 0.600447 | 0.759068 | 0.663802 | 0.025* | |
N2A | 0.60446 (10) | 0.52113 (13) | 0.72611 (9) | 0.0168 (4) | |
H2AA | 0.578269 | 0.481653 | 0.751346 | 0.025* | |
N3A | 0.51041 (10) | 0.65949 (14) | 0.72898 (10) | 0.0191 (4) | |
H3AC | 0.486887 | 0.612044 | 0.758321 | 0.029* | |
H3AB | 0.499668 | 0.725795 | 0.722589 | 0.029* | |
O1 | 0.74783 (9) | 0.50027 (12) | 0.90086 (9) | 0.0257 (4) | |
O1A | 0.75840 (8) | 1.06343 (11) | 0.63623 (8) | 0.0204 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0142 (11) | 0.0231 (11) | 0.0225 (11) | 0.0005 (9) | 0.0049 (9) | 0.0014 (9) |
C2 | 0.0193 (11) | 0.0180 (11) | 0.0206 (11) | −0.0005 (9) | 0.0003 (9) | 0.0006 (9) |
C3 | 0.0187 (12) | 0.0300 (13) | 0.0230 (11) | −0.0075 (10) | 0.0062 (9) | 0.0003 (10) |
C4 | 0.0160 (11) | 0.0293 (12) | 0.0257 (12) | −0.0033 (9) | 0.0074 (9) | −0.0085 (10) |
C5 | 0.0195 (12) | 0.0259 (12) | 0.0303 (12) | 0.0034 (10) | 0.0054 (10) | −0.0066 (10) |
C6 | 0.0261 (13) | 0.0198 (11) | 0.0260 (12) | 0.0059 (9) | 0.0070 (10) | 0.0005 (9) |
C7 | 0.0184 (11) | 0.0179 (10) | 0.0163 (10) | 0.0042 (9) | 0.0037 (8) | 0.0018 (9) |
C8 | 0.0133 (10) | 0.0199 (11) | 0.0119 (9) | 0.0016 (8) | 0.0005 (8) | −0.0008 (8) |
C9 | 0.0160 (11) | 0.0188 (11) | 0.0137 (10) | −0.0006 (8) | 0.0015 (8) | −0.0008 (8) |
C10 | 0.0161 (11) | 0.0226 (11) | 0.0156 (10) | −0.0015 (9) | 0.0016 (8) | −0.0048 (9) |
C11 | 0.0212 (12) | 0.0166 (10) | 0.0191 (10) | 0.0054 (9) | 0.0054 (9) | 0.0032 (9) |
C12 | 0.0187 (11) | 0.0153 (10) | 0.0114 (9) | −0.0001 (8) | 0.0024 (8) | 0.0003 (8) |
C13 | 0.0182 (11) | 0.0170 (11) | 0.0180 (10) | 0.0045 (9) | 0.0082 (9) | 0.0009 (9) |
C14 | 0.0225 (12) | 0.0223 (11) | 0.0178 (11) | 0.0046 (9) | 0.0067 (9) | 0.0061 (9) |
C15 | 0.0249 (12) | 0.0191 (11) | 0.0302 (12) | −0.0005 (9) | 0.0103 (10) | −0.0028 (10) |
C16 | 0.0180 (12) | 0.0288 (12) | 0.0256 (12) | −0.0014 (9) | 0.0082 (9) | −0.0094 (10) |
C17 | 0.0326 (14) | 0.0318 (13) | 0.0184 (11) | 0.0055 (11) | 0.0035 (10) | −0.0007 (10) |
C18 | 0.0326 (13) | 0.0193 (11) | 0.0242 (12) | 0.0057 (10) | 0.0046 (10) | 0.0046 (10) |
C19 | 0.0241 (12) | 0.0232 (12) | 0.0311 (12) | −0.0080 (10) | 0.0010 (10) | 0.0079 (10) |
C1A | 0.0128 (10) | 0.0187 (10) | 0.0153 (10) | 0.0010 (8) | 0.0031 (8) | 0.0002 (8) |
C2A | 0.0199 (11) | 0.0151 (10) | 0.0145 (10) | 0.0000 (9) | −0.0009 (8) | −0.0006 (8) |
C3A | 0.0198 (11) | 0.0204 (11) | 0.0222 (11) | −0.0080 (9) | 0.0064 (9) | −0.0004 (9) |
C4A | 0.0178 (11) | 0.0250 (12) | 0.0244 (11) | −0.0015 (9) | 0.0088 (9) | −0.0038 (10) |
C5A | 0.0185 (12) | 0.0217 (11) | 0.0282 (12) | −0.0019 (9) | 0.0068 (9) | −0.0067 (10) |
C6A | 0.0172 (11) | 0.0144 (10) | 0.0270 (11) | 0.0003 (9) | 0.0018 (9) | −0.0044 (9) |
C7A | 0.0160 (11) | 0.0156 (10) | 0.0138 (10) | −0.0010 (8) | −0.0006 (8) | −0.0023 (8) |
C8A | 0.0127 (10) | 0.0164 (10) | 0.0117 (9) | 0.0008 (8) | −0.0002 (8) | −0.0012 (8) |
C9A | 0.0136 (10) | 0.0164 (10) | 0.0126 (10) | −0.0025 (8) | −0.0025 (8) | −0.0003 (8) |
C10A | 0.0147 (11) | 0.0194 (11) | 0.0177 (10) | −0.0004 (9) | 0.0031 (8) | −0.0030 (9) |
C11A | 0.0181 (11) | 0.0123 (10) | 0.0159 (10) | 0.0034 (8) | 0.0019 (8) | 0.0005 (8) |
C12A | 0.0167 (11) | 0.0164 (10) | 0.0115 (9) | −0.0014 (8) | −0.0002 (8) | −0.0020 (8) |
C13A | 0.0139 (10) | 0.0131 (10) | 0.0183 (10) | 0.0003 (8) | 0.0026 (8) | −0.0006 (8) |
C14A | 0.0180 (11) | 0.0190 (11) | 0.0165 (10) | 0.0031 (9) | 0.0048 (8) | 0.0017 (9) |
C15A | 0.0203 (12) | 0.0111 (10) | 0.0317 (12) | −0.0002 (9) | 0.0118 (9) | −0.0029 (9) |
C16A | 0.0172 (11) | 0.0240 (12) | 0.0257 (12) | −0.0061 (9) | 0.0088 (9) | −0.0109 (10) |
C17A | 0.0335 (14) | 0.0291 (13) | 0.0173 (11) | −0.0069 (10) | 0.0029 (10) | −0.0005 (10) |
C18A | 0.0308 (13) | 0.0166 (11) | 0.0217 (11) | −0.0061 (9) | 0.0020 (10) | 0.0017 (9) |
C19A | 0.0223 (12) | 0.0147 (11) | 0.0319 (12) | −0.0042 (9) | 0.0057 (10) | 0.0047 (9) |
Cl1 | 0.0190 (3) | 0.0133 (2) | 0.0242 (3) | 0.0006 (2) | 0.0072 (2) | −0.0026 (2) |
Cl1A | 0.0175 (3) | 0.0140 (2) | 0.0232 (3) | 0.0014 (2) | 0.0055 (2) | −0.0020 (2) |
F1 | 0.0510 (9) | 0.0230 (7) | 0.0269 (7) | −0.0016 (6) | −0.0008 (6) | 0.0078 (6) |
F1A | 0.0418 (8) | 0.0191 (6) | 0.0231 (7) | −0.0035 (6) | 0.0005 (6) | 0.0069 (5) |
N1 | 0.0159 (9) | 0.0107 (8) | 0.0256 (9) | 0.0010 (7) | 0.0082 (7) | −0.0018 (7) |
N2 | 0.0232 (10) | 0.0138 (9) | 0.0238 (9) | 0.0012 (7) | 0.0135 (8) | 0.0034 (7) |
N3 | 0.0196 (10) | 0.0118 (8) | 0.0293 (10) | 0.0007 (7) | 0.0132 (8) | 0.0023 (7) |
N1A | 0.0159 (9) | 0.0106 (8) | 0.0233 (9) | 0.0009 (7) | 0.0051 (7) | 0.0031 (7) |
N2A | 0.0227 (10) | 0.0131 (9) | 0.0162 (9) | 0.0001 (7) | 0.0076 (7) | 0.0029 (7) |
N3A | 0.0197 (10) | 0.0135 (9) | 0.0261 (10) | −0.0006 (7) | 0.0091 (8) | 0.0018 (7) |
O1 | 0.0208 (8) | 0.0184 (8) | 0.0397 (9) | −0.0029 (6) | 0.0101 (7) | 0.0052 (7) |
O1A | 0.0191 (8) | 0.0128 (7) | 0.0306 (8) | −0.0023 (6) | 0.0080 (6) | 0.0012 (6) |
Geometric parameters (Å, º) top
C1—C2 | 1.388 (3) | C2A—C3A | 1.383 (3) |
C1—C9 | 1.393 (3) | C3A—C4A | 1.389 (3) |
C1—H1 | 0.9300 | C3A—H3A | 0.9300 |
C2—O1 | 1.374 (2) | C4A—C10A | 1.385 (3) |
C2—C3 | 1.384 (3) | C4A—H4A | 0.9300 |
C3—C4 | 1.393 (3) | C5A—C10A | 1.506 (3) |
C3—H3 | 0.9300 | C5A—C6A | 1.521 (3) |
C4—C10 | 1.383 (3) | C5A—H5A1 | 0.9700 |
C4—H4 | 0.9300 | C5A—H5A2 | 0.9700 |
C5—C10 | 1.509 (3) | C6A—C7A | 1.500 (3) |
C5—C6 | 1.514 (3) | C6A—H6A1 | 0.9700 |
C5—H5A | 0.9700 | C6A—H6A2 | 0.9700 |
C5—H5B | 0.9700 | C7A—C8A | 1.340 (3) |
C6—C7 | 1.506 (3) | C7A—C11A | 1.502 (3) |
C6—H6A | 0.9700 | C8A—N1A | 1.413 (2) |
C6—H6B | 0.9700 | C8A—C9A | 1.473 (3) |
C7—C8 | 1.333 (3) | C9A—C10A | 1.409 (3) |
C7—C11 | 1.504 (3) | C11A—N2A | 1.463 (2) |
C8—N1 | 1.409 (2) | C11A—C13A | 1.530 (3) |
C8—C9 | 1.472 (3) | C11A—H11A | 0.9800 |
C9—C10 | 1.409 (3) | C12A—N2A | 1.323 (3) |
C11—N2 | 1.474 (2) | C12A—N3A | 1.327 (3) |
C11—C13 | 1.517 (3) | C12A—N1A | 1.336 (2) |
C11—H11 | 0.9800 | C13A—C14A | 1.383 (3) |
C12—N2 | 1.321 (2) | C13A—C18A | 1.388 (3) |
C12—N3 | 1.327 (2) | C14A—F1A | 1.367 (2) |
C12—N1 | 1.332 (2) | C14A—C15A | 1.374 (3) |
C13—C14 | 1.380 (3) | C15A—C16A | 1.381 (3) |
C13—C18 | 1.395 (3) | C15A—H15A | 0.9300 |
C14—F1 | 1.367 (2) | C16A—C17A | 1.383 (3) |
C14—C15 | 1.377 (3) | C16A—H16A | 0.9300 |
C15—C16 | 1.380 (3) | C17A—C18A | 1.382 (3) |
C15—H15 | 0.9300 | C17A—H17A | 0.9300 |
C16—C17 | 1.383 (3) | C18A—H18A | 0.9300 |
C16—H16 | 0.9300 | C19A—O1A | 1.430 (2) |
C17—C18 | 1.384 (3) | C19A—H19D | 0.9600 |
C17—H17 | 0.9300 | C19A—H19E | 0.9600 |
C18—H18 | 0.9300 | C19A—H19F | 0.9600 |
C19—O1 | 1.426 (2) | N1—H1A | 0.8285 |
C19—H19A | 0.9600 | N2—H2A | 0.8310 |
C19—H19B | 0.9600 | N3—H3B | 0.8185 |
C19—H19C | 0.9600 | N3—H3C | 0.8383 |
C1A—C9A | 1.388 (3) | N1A—H1AA | 0.8043 |
C1A—C2A | 1.390 (3) | N2A—H2AA | 0.8280 |
C1A—H1B | 0.9300 | N3A—H3AC | 0.9021 |
C2A—O1A | 1.377 (2) | N3A—H3AB | 0.8059 |
| | | |
C2—C1—C9 | 120.61 (19) | C10A—C4A—H4A | 119.0 |
C2—C1—H1 | 119.7 | C3A—C4A—H4A | 119.0 |
C9—C1—H1 | 119.7 | C10A—C5A—C6A | 112.67 (17) |
O1—C2—C3 | 124.89 (19) | C10A—C5A—H5A1 | 109.1 |
O1—C2—C1 | 114.81 (18) | C6A—C5A—H5A1 | 109.1 |
C3—C2—C1 | 120.30 (19) | C10A—C5A—H5A2 | 109.1 |
C2—C3—C4 | 118.7 (2) | C6A—C5A—H5A2 | 109.1 |
C2—C3—H3 | 120.6 | H5A1—C5A—H5A2 | 107.8 |
C4—C3—H3 | 120.6 | C7A—C6A—C5A | 111.45 (17) |
C10—C4—C3 | 122.3 (2) | C7A—C6A—H6A1 | 109.3 |
C10—C4—H4 | 118.8 | C5A—C6A—H6A1 | 109.3 |
C3—C4—H4 | 118.8 | C7A—C6A—H6A2 | 109.3 |
C10—C5—C6 | 113.39 (18) | C5A—C6A—H6A2 | 109.3 |
C10—C5—H5A | 108.9 | H6A1—C6A—H6A2 | 108.0 |
C6—C5—H5A | 108.9 | C8A—C7A—C6A | 120.74 (18) |
C10—C5—H5B | 108.9 | C8A—C7A—C11A | 121.53 (18) |
C6—C5—H5B | 108.9 | C6A—C7A—C11A | 117.55 (17) |
H5A—C5—H5B | 107.7 | C7A—C8A—N1A | 119.55 (18) |
C7—C6—C5 | 110.65 (17) | C7A—C8A—C9A | 122.62 (18) |
C7—C6—H6A | 109.5 | N1A—C8A—C9A | 117.72 (16) |
C5—C6—H6A | 109.5 | C1A—C9A—C10A | 120.06 (18) |
C7—C6—H6B | 109.5 | C1A—C9A—C8A | 122.75 (18) |
C5—C6—H6B | 109.5 | C10A—C9A—C8A | 117.16 (17) |
H6A—C6—H6B | 108.1 | C4A—C10A—C9A | 118.23 (18) |
C8—C7—C11 | 122.20 (18) | C4A—C10A—C5A | 122.09 (18) |
C8—C7—C6 | 121.12 (19) | C9A—C10A—C5A | 119.62 (18) |
C11—C7—C6 | 116.68 (17) | N2A—C11A—C7A | 110.22 (15) |
C7—C8—N1 | 120.28 (18) | N2A—C11A—C13A | 109.47 (16) |
C7—C8—C9 | 122.77 (18) | C7A—C11A—C13A | 113.38 (16) |
N1—C8—C9 | 116.95 (17) | N2A—C11A—H11A | 107.9 |
C1—C9—C10 | 119.73 (19) | C7A—C11A—H11A | 107.9 |
C1—C9—C8 | 122.83 (18) | C13A—C11A—H11A | 107.9 |
C10—C9—C8 | 117.43 (18) | N2A—C12A—N3A | 120.54 (18) |
C4—C10—C9 | 118.27 (19) | N2A—C12A—N1A | 119.77 (18) |
C4—C10—C5 | 122.49 (19) | N3A—C12A—N1A | 119.68 (18) |
C9—C10—C5 | 118.98 (18) | C14A—C13A—C18A | 116.28 (18) |
N2—C11—C7 | 110.10 (16) | C14A—C13A—C11A | 121.35 (17) |
N2—C11—C13 | 108.43 (17) | C18A—C13A—C11A | 122.34 (17) |
C7—C11—C13 | 114.15 (16) | F1A—C14A—C15A | 118.13 (17) |
N2—C11—H11 | 108.0 | F1A—C14A—C13A | 117.73 (17) |
C7—C11—H11 | 108.0 | C15A—C14A—C13A | 124.13 (19) |
C13—C11—H11 | 108.0 | C14A—C15A—C16A | 117.97 (19) |
N2—C12—N3 | 120.18 (18) | C14A—C15A—H15A | 121.0 |
N2—C12—N1 | 119.97 (18) | C16A—C15A—H15A | 121.0 |
N3—C12—N1 | 119.83 (17) | C15A—C16A—C17A | 120.1 (2) |
C14—C13—C18 | 116.50 (19) | C15A—C16A—H16A | 120.0 |
C14—C13—C11 | 121.44 (18) | C17A—C16A—H16A | 120.0 |
C18—C13—C11 | 121.95 (18) | C18A—C17A—C16A | 120.3 (2) |
F1—C14—C15 | 118.03 (18) | C18A—C17A—H17A | 119.9 |
F1—C14—C13 | 118.00 (18) | C16A—C17A—H17A | 119.9 |
C15—C14—C13 | 123.94 (19) | C17A—C18A—C13A | 121.27 (19) |
C14—C15—C16 | 118.1 (2) | C17A—C18A—H18A | 119.4 |
C14—C15—H15 | 120.9 | C13A—C18A—H18A | 119.4 |
C16—C15—H15 | 120.9 | O1A—C19A—H19D | 109.5 |
C15—C16—C17 | 120.2 (2) | O1A—C19A—H19E | 109.5 |
C15—C16—H16 | 119.9 | H19D—C19A—H19E | 109.5 |
C17—C16—H16 | 119.9 | O1A—C19A—H19F | 109.5 |
C16—C17—C18 | 120.2 (2) | H19D—C19A—H19F | 109.5 |
C16—C17—H17 | 119.9 | H19E—C19A—H19F | 109.5 |
C18—C17—H17 | 119.9 | C12—N1—C8 | 121.66 (17) |
C17—C18—C13 | 121.1 (2) | C12—N1—H1A | 115.6 |
C17—C18—H18 | 119.5 | C8—N1—H1A | 122.5 |
C13—C18—H18 | 119.5 | C12—N2—C11 | 125.61 (17) |
O1—C19—H19A | 109.5 | C12—N2—H2A | 114.9 |
O1—C19—H19B | 109.5 | C11—N2—H2A | 119.4 |
H19A—C19—H19B | 109.5 | C12—N3—H3B | 116.9 |
O1—C19—H19C | 109.5 | C12—N3—H3C | 119.4 |
H19A—C19—H19C | 109.5 | H3B—N3—H3C | 121.1 |
H19B—C19—H19C | 109.5 | C12A—N1A—C8A | 121.38 (16) |
C9A—C1A—C2A | 120.30 (18) | C12A—N1A—H1AA | 116.4 |
C9A—C1A—H1B | 119.9 | C8A—N1A—H1AA | 122.0 |
C2A—C1A—H1B | 119.9 | C12A—N2A—C11A | 124.26 (16) |
O1A—C2A—C3A | 124.33 (18) | C12A—N2A—H2AA | 115.9 |
O1A—C2A—C1A | 115.31 (18) | C11A—N2A—H2AA | 119.1 |
C3A—C2A—C1A | 120.35 (18) | C12A—N3A—H3AC | 117.4 |
C2A—C3A—C4A | 119.01 (19) | C12A—N3A—H3AB | 116.5 |
C2A—C3A—H3A | 120.5 | H3AC—N3A—H3AB | 124.3 |
C4A—C3A—H3A | 120.5 | C2—O1—C19 | 117.09 (17) |
C10A—C4A—C3A | 122.04 (19) | C2A—O1A—C19A | 117.32 (16) |
| | | |
C9—C1—C2—O1 | 177.65 (18) | C6A—C7A—C8A—C9A | −1.0 (3) |
C9—C1—C2—C3 | −2.0 (3) | C11A—C7A—C8A—C9A | 173.92 (17) |
O1—C2—C3—C4 | −177.24 (19) | C2A—C1A—C9A—C10A | 0.0 (3) |
C1—C2—C3—C4 | 2.4 (3) | C2A—C1A—C9A—C8A | 177.95 (18) |
C2—C3—C4—C10 | −0.7 (3) | C7A—C8A—C9A—C1A | −163.65 (19) |
C10—C5—C6—C7 | 45.2 (2) | N1A—C8A—C9A—C1A | 12.6 (3) |
C5—C6—C7—C8 | −30.5 (3) | C7A—C8A—C9A—C10A | 14.4 (3) |
C5—C6—C7—C11 | 149.43 (19) | N1A—C8A—C9A—C10A | −169.42 (17) |
C11—C7—C8—N1 | 3.0 (3) | C3A—C4A—C10A—C9A | 0.1 (3) |
C6—C7—C8—N1 | −177.12 (18) | C3A—C4A—C10A—C5A | 177.21 (19) |
C11—C7—C8—C9 | −177.63 (18) | C1A—C9A—C10A—C4A | 0.2 (3) |
C6—C7—C8—C9 | 2.3 (3) | C8A—C9A—C10A—C4A | −177.87 (18) |
C2—C1—C9—C10 | 0.0 (3) | C1A—C9A—C10A—C5A | −177.02 (18) |
C2—C1—C9—C8 | −179.60 (19) | C8A—C9A—C10A—C5A | 4.9 (3) |
C7—C8—C9—C1 | −169.7 (2) | C6A—C5A—C10A—C4A | 148.3 (2) |
N1—C8—C9—C1 | 9.7 (3) | C6A—C5A—C10A—C9A | −34.6 (3) |
C7—C8—C9—C10 | 10.7 (3) | C8A—C7A—C11A—N2A | −12.2 (3) |
N1—C8—C9—C10 | −169.86 (17) | C6A—C7A—C11A—N2A | 162.94 (16) |
C3—C4—C10—C9 | −1.2 (3) | C8A—C7A—C11A—C13A | 110.9 (2) |
C3—C4—C10—C5 | 172.8 (2) | C6A—C7A—C11A—C13A | −74.0 (2) |
C1—C9—C10—C4 | 1.6 (3) | N2A—C11A—C13A—C14A | −90.2 (2) |
C8—C9—C10—C4 | −178.80 (18) | C7A—C11A—C13A—C14A | 146.27 (19) |
C1—C9—C10—C5 | −172.61 (19) | N2A—C11A—C13A—C18A | 87.5 (2) |
C8—C9—C10—C5 | 7.0 (3) | C7A—C11A—C13A—C18A | −36.0 (3) |
C6—C5—C10—C4 | 150.5 (2) | C18A—C13A—C14A—F1A | −179.22 (18) |
C6—C5—C10—C9 | −35.5 (3) | C11A—C13A—C14A—F1A | −1.4 (3) |
C8—C7—C11—N2 | 0.2 (3) | C18A—C13A—C14A—C15A | 0.6 (3) |
C6—C7—C11—N2 | −179.68 (17) | C11A—C13A—C14A—C15A | 178.40 (19) |
C8—C7—C11—C13 | −122.0 (2) | F1A—C14A—C15A—C16A | 178.81 (17) |
C6—C7—C11—C13 | 58.1 (2) | C13A—C14A—C15A—C16A | −1.0 (3) |
N2—C11—C13—C14 | 97.3 (2) | C14A—C15A—C16A—C17A | 0.6 (3) |
C7—C11—C13—C14 | −139.5 (2) | C15A—C16A—C17A—C18A | 0.2 (3) |
N2—C11—C13—C18 | −78.8 (2) | C16A—C17A—C18A—C13A | −0.6 (3) |
C7—C11—C13—C18 | 44.3 (3) | C14A—C13A—C18A—C17A | 0.3 (3) |
C18—C13—C14—F1 | 177.89 (18) | C11A—C13A—C18A—C17A | −177.5 (2) |
C11—C13—C14—F1 | 1.5 (3) | N2—C12—N1—C8 | −0.4 (3) |
C18—C13—C14—C15 | 0.0 (3) | N3—C12—N1—C8 | 178.09 (17) |
C11—C13—C14—C15 | −176.4 (2) | C7—C8—N1—C12 | −3.1 (3) |
F1—C14—C15—C16 | −177.56 (18) | C9—C8—N1—C12 | 177.50 (17) |
C13—C14—C15—C16 | 0.4 (3) | N3—C12—N2—C11 | −174.38 (18) |
C14—C15—C16—C17 | −0.6 (3) | N1—C12—N2—C11 | 4.1 (3) |
C15—C16—C17—C18 | 0.5 (3) | C7—C11—N2—C12 | −3.9 (3) |
C16—C17—C18—C13 | −0.2 (3) | C13—C11—N2—C12 | 121.6 (2) |
C14—C13—C18—C17 | −0.1 (3) | N2A—C12A—N1A—C8A | −4.5 (3) |
C11—C13—C18—C17 | 176.3 (2) | N3A—C12A—N1A—C8A | 176.21 (17) |
C9A—C1A—C2A—O1A | −179.72 (17) | C7A—C8A—N1A—C12A | 11.9 (3) |
C9A—C1A—C2A—C3A | −0.4 (3) | C9A—C8A—N1A—C12A | −164.50 (17) |
O1A—C2A—C3A—C4A | 179.90 (18) | N3A—C12A—N2A—C11A | 166.43 (18) |
C1A—C2A—C3A—C4A | 0.7 (3) | N1A—C12A—N2A—C11A | −12.8 (3) |
C2A—C3A—C4A—C10A | −0.5 (3) | C7A—C11A—N2A—C12A | 20.3 (3) |
C10A—C5A—C6A—C7A | 45.0 (2) | C13A—C11A—N2A—C12A | −105.1 (2) |
C5A—C6A—C7A—C8A | −29.1 (3) | C3—C2—O1—C19 | −1.4 (3) |
C5A—C6A—C7A—C11A | 155.78 (17) | C1—C2—O1—C19 | 178.97 (18) |
C6A—C7A—C8A—N1A | −177.20 (17) | C3A—C2A—O1A—C19A | 3.0 (3) |
C11A—C7A—C8A—N1A | −2.2 (3) | C1A—C2A—O1A—C19A | −177.73 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3A—H3AB···Cl1A | 0.81 | 2.49 | 3.2427 (17) | 155 |
N3A—H3AC···Cl1Ai | 0.90 | 2.54 | 3.3496 (17) | 150 |
N2A—H2AA···Cl1Ai | 0.83 | 2.37 | 3.1736 (17) | 163 |
N1A—H1AA···Cl1A | 0.80 | 2.42 | 3.1841 (17) | 158 |
N3—H3C···Cl1ii | 0.84 | 2.48 | 3.2318 (17) | 149 |
N3—H3B···Cl1 | 0.82 | 2.44 | 3.1903 (17) | 154 |
N2—H2A···Cl1ii | 0.83 | 2.36 | 3.1433 (17) | 158 |
N1—H1A···Cl1 | 0.83 | 2.40 | 3.1766 (16) | 156 |
C15A—H15A···Cl1Aiii | 0.93 | 2.84 | 3.720 (2) | 159 |
C1A—H1B···Cl1A | 0.93 | 2.93 | 3.816 (2) | 160 |
C19—H19C···Cl1Ai | 0.96 | 2.81 | 3.736 (2) | 162 |
C15—H15···Cl1iv | 0.93 | 2.96 | 3.796 (2) | 151 |
C11—H11···O1A | 0.98 | 2.57 | 3.265 (3) | 128 |
C1—H1···Cl1 | 0.93 | 2.91 | 3.818 (2) | 167 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+2, y+1/2, −z+3/2; (iii) x, y−1, z; (iv) x, y+1, z. |
2-Amino-4-(4-fluorophenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[
h]quinazolin-3-ium chloride (4HF)
top
Crystal data top
C19H19FN3O+·Cl− | F(000) = 752 |
Mr = 359.82 | Dx = 1.366 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.7725 (9) Å | Cell parameters from 3293 reflections |
b = 11.9161 (10) Å | θ = 2.9–29.2° |
c = 17.1473 (15) Å | µ = 0.24 mm−1 |
β = 102.626 (10)° | T = 100 K |
V = 1749.1 (3) Å3 | Block, yellow |
Z = 4 | 0.14 × 0.13 × 0.12 mm |
Data collection top
Rigaku OD SuperNova Dual source diffractometer with an AtlasS2 detector | 3252 independent reflections |
Radiation source: micro-focus sealed X-ray tube | 2698 reflections with I > 2σ(I) |
Detector resolution: 5.2684 pixels mm-1 | Rint = 0.038 |
CCD plate scans | θmax = 25.5°, θmin = 2.1° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | h = −6→10 |
Tmin = 0.623, Tmax = 1.000 | k = −14→12 |
7647 measured reflections | l = −20→19 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.126 | w = 1/[σ2(Fo2) + (0.0568P)2 + 0.5265P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
3252 reflections | Δρmax = 0.44 e Å−3 |
227 parameters | Δρmin = −0.28 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.7237 (3) | 0.41733 (18) | 0.01749 (12) | 0.0220 (5) | |
H1 | 0.685629 | 0.391456 | 0.060749 | 0.026* | |
C2 | 0.7722 (3) | 0.34112 (18) | −0.03294 (13) | 0.0240 (5) | |
C3 | 0.8267 (3) | 0.3780 (2) | −0.09863 (14) | 0.0298 (6) | |
H3 | 0.858213 | 0.327105 | −0.133078 | 0.036* | |
C4 | 0.8330 (3) | 0.4930 (2) | −0.11171 (14) | 0.0301 (6) | |
H4 | 0.869802 | 0.518080 | −0.155538 | 0.036* | |
C5 | 0.8048 (3) | 0.6958 (2) | −0.07423 (14) | 0.0287 (6) | |
H5A | 0.793537 | 0.710667 | −0.130825 | 0.034* | |
H5B | 0.909185 | 0.718567 | −0.047246 | 0.034* | |
C6 | 0.6859 (3) | 0.76604 (19) | −0.04282 (13) | 0.0268 (5) | |
H6A | 0.720334 | 0.843593 | −0.038034 | 0.032* | |
H6B | 0.586342 | 0.763266 | −0.080872 | 0.032* | |
C7 | 0.6646 (3) | 0.72529 (18) | 0.03717 (13) | 0.0223 (5) | |
C8 | 0.6820 (3) | 0.61643 (19) | 0.05654 (12) | 0.0208 (5) | |
C9 | 0.7312 (3) | 0.53259 (19) | 0.00423 (12) | 0.0217 (5) | |
C10 | 0.7867 (3) | 0.57126 (19) | −0.06215 (13) | 0.0243 (5) | |
C11 | 0.6067 (3) | 0.80917 (19) | 0.08976 (13) | 0.0235 (5) | |
H11 | 0.515783 | 0.847237 | 0.057131 | 0.028* | |
C12 | 0.5789 (3) | 0.64421 (19) | 0.17382 (13) | 0.0226 (5) | |
C13 | 0.7269 (3) | 0.89892 (18) | 0.12430 (12) | 0.0215 (5) | |
C14 | 0.8745 (3) | 0.86765 (19) | 0.16765 (14) | 0.0264 (5) | |
H14 | 0.899674 | 0.791916 | 0.174142 | 0.032* | |
C15 | 0.9841 (3) | 0.9475 (2) | 0.20118 (14) | 0.0299 (6) | |
H15 | 1.082311 | 0.926620 | 0.230247 | 0.036* | |
C16 | 0.9433 (3) | 1.0583 (2) | 0.19013 (14) | 0.0308 (6) | |
C17 | 0.7997 (3) | 1.0935 (2) | 0.14859 (14) | 0.0336 (6) | |
H17 | 0.775413 | 1.169412 | 0.142865 | 0.040* | |
C18 | 0.6917 (3) | 1.01208 (19) | 0.11531 (13) | 0.0282 (6) | |
H18 | 0.593781 | 1.034006 | 0.086438 | 0.034* | |
C19 | 0.8260 (3) | 0.1480 (2) | −0.05647 (15) | 0.0314 (6) | |
H19A | 0.771824 | 0.150163 | −0.111524 | 0.047* | |
H19B | 0.815415 | 0.074746 | −0.034969 | 0.047* | |
H19C | 0.934652 | 0.164097 | −0.052610 | 0.047* | |
Cl1 | 0.61929 (7) | 0.34193 (5) | 0.21592 (3) | 0.02544 (19) | |
F1 | 1.0514 (2) | 1.13792 (13) | 0.22292 (9) | 0.0471 (4) | |
N1 | 0.6463 (2) | 0.57731 (15) | 0.12857 (10) | 0.0233 (4) | |
H1A | 0.653950 | 0.506828 | 0.140628 | 0.035* | |
N2 | 0.5551 (2) | 0.75145 (16) | 0.15503 (11) | 0.0254 (5) | |
H2A | 0.510166 | 0.789471 | 0.188447 | 0.038* | |
N3 | 0.5390 (2) | 0.60322 (16) | 0.23876 (11) | 0.0262 (5) | |
H3A | 0.477973 | 0.652851 | 0.264895 | 0.039* | |
H3B | 0.534473 | 0.521451 | 0.242195 | 0.039* | |
O1 | 0.76094 (19) | 0.22971 (13) | −0.01237 (9) | 0.0278 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0224 (13) | 0.0237 (12) | 0.0212 (11) | −0.0021 (10) | 0.0078 (9) | 0.0007 (9) |
C2 | 0.0212 (12) | 0.0233 (12) | 0.0271 (12) | −0.0011 (10) | 0.0047 (9) | 0.0012 (10) |
C3 | 0.0354 (15) | 0.0292 (13) | 0.0279 (12) | −0.0022 (11) | 0.0135 (11) | −0.0073 (11) |
C4 | 0.0353 (15) | 0.0320 (14) | 0.0279 (12) | −0.0036 (11) | 0.0180 (11) | 0.0012 (11) |
C5 | 0.0334 (15) | 0.0286 (13) | 0.0267 (12) | −0.0064 (11) | 0.0125 (10) | 0.0004 (10) |
C6 | 0.0320 (14) | 0.0214 (12) | 0.0272 (12) | −0.0051 (10) | 0.0070 (10) | 0.0018 (10) |
C7 | 0.0203 (12) | 0.0212 (12) | 0.0258 (11) | −0.0026 (9) | 0.0060 (9) | 0.0001 (9) |
C8 | 0.0182 (12) | 0.0232 (12) | 0.0219 (11) | −0.0010 (9) | 0.0064 (9) | 0.0019 (10) |
C9 | 0.0166 (12) | 0.0252 (12) | 0.0238 (11) | −0.0006 (9) | 0.0052 (9) | 0.0013 (9) |
C10 | 0.0242 (13) | 0.0242 (12) | 0.0257 (11) | −0.0014 (10) | 0.0082 (10) | 0.0013 (10) |
C11 | 0.0213 (13) | 0.0210 (12) | 0.0290 (12) | 0.0035 (10) | 0.0073 (10) | 0.0059 (10) |
C12 | 0.0220 (13) | 0.0223 (12) | 0.0251 (11) | 0.0008 (10) | 0.0089 (10) | −0.0018 (10) |
C13 | 0.0239 (13) | 0.0202 (12) | 0.0240 (11) | 0.0022 (9) | 0.0129 (9) | 0.0014 (9) |
C14 | 0.0271 (14) | 0.0209 (12) | 0.0338 (12) | 0.0050 (10) | 0.0123 (10) | −0.0002 (10) |
C15 | 0.0253 (13) | 0.0341 (14) | 0.0323 (13) | 0.0001 (11) | 0.0109 (10) | −0.0085 (11) |
C16 | 0.0386 (16) | 0.0271 (13) | 0.0310 (13) | −0.0112 (12) | 0.0169 (11) | −0.0081 (11) |
C17 | 0.0536 (18) | 0.0153 (12) | 0.0344 (13) | 0.0005 (12) | 0.0151 (12) | 0.0008 (11) |
C18 | 0.0339 (14) | 0.0234 (12) | 0.0289 (12) | 0.0083 (11) | 0.0103 (10) | 0.0043 (10) |
C19 | 0.0329 (15) | 0.0271 (13) | 0.0362 (13) | 0.0030 (11) | 0.0118 (11) | −0.0048 (11) |
Cl1 | 0.0298 (4) | 0.0200 (3) | 0.0292 (3) | −0.0009 (2) | 0.0124 (2) | 0.0028 (2) |
F1 | 0.0534 (11) | 0.0371 (9) | 0.0523 (9) | −0.0186 (8) | 0.0149 (8) | −0.0149 (7) |
N1 | 0.0290 (11) | 0.0163 (9) | 0.0274 (10) | 0.0031 (8) | 0.0121 (8) | 0.0036 (8) |
N2 | 0.0297 (12) | 0.0180 (10) | 0.0335 (10) | 0.0019 (9) | 0.0177 (9) | 0.0021 (8) |
N3 | 0.0329 (12) | 0.0187 (10) | 0.0315 (10) | 0.0029 (9) | 0.0168 (9) | 0.0023 (8) |
O1 | 0.0329 (10) | 0.0205 (9) | 0.0340 (9) | 0.0023 (7) | 0.0163 (7) | −0.0026 (7) |
Geometric parameters (Å, º) top
C1—C2 | 1.383 (3) | C11—H11 | 0.9800 |
C1—C9 | 1.396 (3) | C12—N2 | 1.323 (3) |
C1—H1 | 0.9300 | C12—N3 | 1.331 (3) |
C2—O1 | 1.383 (3) | C12—N1 | 1.337 (3) |
C2—C3 | 1.388 (3) | C13—C18 | 1.384 (3) |
C3—C4 | 1.391 (3) | C13—C14 | 1.395 (3) |
C3—H3 | 0.9300 | C14—C15 | 1.386 (3) |
C4—C10 | 1.381 (3) | C14—H14 | 0.9300 |
C4—H4 | 0.9300 | C15—C16 | 1.370 (3) |
C5—C10 | 1.512 (3) | C15—H15 | 0.9300 |
C5—C6 | 1.524 (3) | C16—C17 | 1.370 (4) |
C5—H5A | 0.9700 | C16—F1 | 1.372 (3) |
C5—H5B | 0.9700 | C17—C18 | 1.389 (3) |
C6—C7 | 1.505 (3) | C17—H17 | 0.9300 |
C6—H6A | 0.9700 | C18—H18 | 0.9300 |
C6—H6B | 0.9700 | C19—O1 | 1.426 (3) |
C7—C8 | 1.339 (3) | C19—H19A | 0.9600 |
C7—C11 | 1.506 (3) | C19—H19B | 0.9600 |
C8—N1 | 1.418 (3) | C19—H19C | 0.9600 |
C8—C9 | 1.469 (3) | N1—H1A | 0.8640 |
C9—C10 | 1.410 (3) | N2—H2A | 0.8876 |
C11—N2 | 1.467 (3) | N3—H3A | 0.9707 |
C11—C13 | 1.527 (3) | N3—H3B | 0.9775 |
| | | |
C2—C1—C9 | 120.8 (2) | C7—C11—H11 | 107.7 |
C2—C1—H1 | 119.6 | C13—C11—H11 | 107.7 |
C9—C1—H1 | 119.6 | N2—C12—N3 | 120.1 (2) |
O1—C2—C1 | 115.0 (2) | N2—C12—N1 | 120.0 (2) |
O1—C2—C3 | 124.6 (2) | N3—C12—N1 | 119.8 (2) |
C1—C2—C3 | 120.5 (2) | C18—C13—C14 | 118.6 (2) |
C2—C3—C4 | 118.4 (2) | C18—C13—C11 | 121.4 (2) |
C2—C3—H3 | 120.8 | C14—C13—C11 | 120.1 (2) |
C4—C3—H3 | 120.8 | C15—C14—C13 | 121.1 (2) |
C10—C4—C3 | 122.6 (2) | C15—C14—H14 | 119.4 |
C10—C4—H4 | 118.7 | C13—C14—H14 | 119.4 |
C3—C4—H4 | 118.7 | C16—C15—C14 | 117.9 (2) |
C10—C5—C6 | 112.98 (19) | C16—C15—H15 | 121.1 |
C10—C5—H5A | 109.0 | C14—C15—H15 | 121.1 |
C6—C5—H5A | 109.0 | C17—C16—C15 | 123.3 (2) |
C10—C5—H5B | 109.0 | C17—C16—F1 | 118.4 (2) |
C6—C5—H5B | 109.0 | C15—C16—F1 | 118.2 (2) |
H5A—C5—H5B | 107.8 | C16—C17—C18 | 117.9 (2) |
C7—C6—C5 | 112.09 (19) | C16—C17—H17 | 121.1 |
C7—C6—H6A | 109.2 | C18—C17—H17 | 121.1 |
C5—C6—H6A | 109.2 | C13—C18—C17 | 121.3 (2) |
C7—C6—H6B | 109.2 | C13—C18—H18 | 119.4 |
C5—C6—H6B | 109.2 | C17—C18—H18 | 119.4 |
H6A—C6—H6B | 107.9 | O1—C19—H19A | 109.5 |
C8—C7—C6 | 120.5 (2) | O1—C19—H19B | 109.5 |
C8—C7—C11 | 122.0 (2) | H19A—C19—H19B | 109.5 |
C6—C7—C11 | 117.18 (18) | O1—C19—H19C | 109.5 |
C7—C8—N1 | 119.9 (2) | H19A—C19—H19C | 109.5 |
C7—C8—C9 | 122.71 (19) | H19B—C19—H19C | 109.5 |
N1—C8—C9 | 117.30 (18) | C12—N1—C8 | 121.30 (18) |
C1—C9—C10 | 119.3 (2) | C12—N1—H1A | 117.5 |
C1—C9—C8 | 122.63 (19) | C8—N1—H1A | 120.5 |
C10—C9—C8 | 118.0 (2) | C12—N2—C11 | 125.46 (19) |
C4—C10—C9 | 118.4 (2) | C12—N2—H2A | 113.8 |
C4—C10—C5 | 121.7 (2) | C11—N2—H2A | 120.5 |
C9—C10—C5 | 119.8 (2) | C12—N3—H3A | 115.8 |
N2—C11—C7 | 110.25 (18) | C12—N3—H3B | 116.0 |
N2—C11—C13 | 109.53 (18) | H3A—N3—H3B | 123.1 |
C7—C11—C13 | 113.74 (19) | C2—O1—C19 | 117.46 (18) |
N2—C11—H11 | 107.7 | | |
| | | |
C9—C1—C2—O1 | 179.0 (2) | C6—C7—C11—N2 | 165.84 (19) |
C9—C1—C2—C3 | −1.2 (3) | C8—C7—C11—C13 | 115.7 (2) |
O1—C2—C3—C4 | −179.4 (2) | C6—C7—C11—C13 | −70.7 (2) |
C1—C2—C3—C4 | 0.8 (4) | N2—C11—C13—C18 | −109.5 (2) |
C2—C3—C4—C10 | −0.2 (4) | C7—C11—C13—C18 | 126.6 (2) |
C10—C5—C6—C7 | 42.8 (3) | N2—C11—C13—C14 | 68.9 (3) |
C5—C6—C7—C8 | −30.8 (3) | C7—C11—C13—C14 | −55.0 (3) |
C5—C6—C7—C11 | 155.5 (2) | C18—C13—C14—C15 | 0.0 (3) |
C6—C7—C8—N1 | −173.6 (2) | C11—C13—C14—C15 | −178.4 (2) |
C11—C7—C8—N1 | −0.2 (3) | C13—C14—C15—C16 | −0.3 (3) |
C6—C7—C8—C9 | 3.7 (3) | C14—C15—C16—C17 | 0.7 (4) |
C11—C7—C8—C9 | 177.0 (2) | C14—C15—C16—F1 | −179.8 (2) |
C2—C1—C9—C10 | 1.0 (3) | C15—C16—C17—C18 | −0.9 (4) |
C2—C1—C9—C8 | −179.5 (2) | F1—C16—C17—C18 | 179.6 (2) |
C7—C8—C9—C1 | −168.7 (2) | C14—C13—C18—C17 | −0.2 (3) |
N1—C8—C9—C1 | 8.7 (3) | C11—C13—C18—C17 | 178.3 (2) |
C7—C8—C9—C10 | 10.8 (3) | C16—C17—C18—C13 | 0.6 (4) |
N1—C8—C9—C10 | −171.83 (19) | N2—C12—N1—C8 | −5.2 (3) |
C3—C4—C10—C9 | 0.1 (4) | N3—C12—N1—C8 | 176.32 (19) |
C3—C4—C10—C5 | 175.8 (2) | C7—C8—N1—C12 | 7.5 (3) |
C1—C9—C10—C4 | −0.4 (3) | C9—C8—N1—C12 | −170.0 (2) |
C8—C9—C10—C4 | −179.9 (2) | N3—C12—N2—C11 | 174.0 (2) |
C1—C9—C10—C5 | −176.2 (2) | N1—C12—N2—C11 | −4.5 (3) |
C8—C9—C10—C5 | 4.3 (3) | C7—C11—N2—C12 | 10.5 (3) |
C6—C5—C10—C4 | 153.1 (2) | C13—C11—N2—C12 | −115.4 (2) |
C6—C5—C10—C9 | −31.2 (3) | C1—C2—O1—C19 | −172.8 (2) |
C8—C7—C11—N2 | −7.8 (3) | C3—C2—O1—C19 | 7.3 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3B···Cl1 | 0.98 | 2.34 | 3.235 (2) | 152 |
N3—H3A···Cl1i | 0.97 | 2.46 | 3.331 (2) | 150 |
N2—H2A···Cl1i | 0.89 | 2.28 | 3.143 (2) | 165 |
N1—H1A···Cl1 | 0.86 | 2.41 | 3.2127 (19) | 155 |
C19—H19A···Cl1ii | 0.96 | 2.97 | 3.929 (3) | 177 |
C17—H17···Cl1iii | 0.93 | 2.90 | 3.661 (3) | 140 |
C15—H15···Cl1iv | 0.93 | 2.77 | 3.681 (3) | 167 |
C11—H11···O1v | 0.98 | 2.55 | 3.242 (3) | 127 |
C1—H1···Cl1 | 0.93 | 2.91 | 3.819 (2) | 168 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, −y+1/2, z−1/2; (iii) x, y+1, z; (iv) −x+2, y+1/2, −z+1/2; (v) −x+1, −y+1, −z. |