New methanesulfonic acid salt forms of the anticonvulsant and analgesic active pharmaceutical ingredient carbamazepine and its closely related structural analogue 10,11-dihydrocarbamazepine have been prepared and characterized by single-crystal X-ray diffraction at 120 and 100 K, respectively {namely [(5H-dibenzo[b,f]azepin-5-yl)(hydroxy)methylidene]azanium methanesulfonate, C15H13N2O+·CH3SO3-, and [(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)(hydroxy)methylidene]azanium methanesulfonate, C15H15N2O+·CH3SO3-}. In light of the structural information obtained, the crystal structure of the carbamazepine trifluoroacetic acid monosolvate [dibenzo[b,f]azepine-5-carboxamide-trifluoroacetic acid (1/1), C15H12N2O·CF3COOH] was redetermined at 100 and 270 K, and from this data it was concluded that the protonation state for this solvate species is best described as in an `intermediate state' with the acidic proton located almost at the mid-point between the acid and base.
Supporting information
CCDC references: 967049; 967050; 967051; 967052
Data collection: SMART (Bruker, 1999) for (3); CrysAlis PRO (Agilent, 2011) for (4), (5), (6). Cell refinement: SMART and SAINT (Bruker, 1999) for (3); CrysAlis PRO (Agilent, 2011) for (4), (5), (6). Data reduction: SAINT (Bruker, 1999) and SHELXTL (Sheldrick, 2008) for (3); CrysAlis PRO (Agilent, 2011) for (4), (5), (6). For all compounds, program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008).
(3) [(5
H-Dibenzo[
b,
f]azepin-5-yl)(hydroxy)methylidene]azanium
methanesulfonate
top
Crystal data top
C15H13N2O+·CH3O3S− | F(000) = 696 |
Mr = 332.37 | Dx = 1.404 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 5.5673 (7) Å | Cell parameters from 876 reflections |
b = 15.7196 (19) Å | θ = 2.6–27.9° |
c = 18.125 (2) Å | µ = 0.23 mm−1 |
β = 97.641 (4)° | T = 120 K |
V = 1572.1 (3) Å3 | Prism, colourless |
Z = 4 | 0.35 × 0.18 × 0.10 mm |
Data collection top
Bruker SMART 1K CCD area-detector diffractometer | 2626 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.033 |
Graphite monochromator | θmax = 26.4°, θmin = 1.7° |
Detector resolution: 8.192 pixels mm-1 | h = −6→6 |
ω scans | k = −19→19 |
13272 measured reflections | l = −22→22 |
3203 independent reflections | |
Refinement top
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.098 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.053P)2 + 0.750P] where P = (Fo2 + 2Fc2)/3 |
3203 reflections | (Δ/σ)max = 0.001 |
221 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
Special details top
Experimental. Single-crystal X-ray data for (3) was measured at 120 K on a Bruker
SMART 1 K X-ray diffractometer equipped with an Oxford Cryosystems Cryostream
cooler using graphite-monochromated Mo Kα (λ = 0.71073 Å) radiation. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.7116 (2) | 0.68279 (8) | 0.37938 (6) | 0.0228 (3) | |
H1A | 0.784 (5) | 0.6329 (19) | 0.3586 (15) | 0.061 (8)* | |
N1 | 0.5566 (3) | 0.73258 (9) | 0.47872 (8) | 0.0194 (3) | |
N2 | 0.8099 (3) | 0.61525 (10) | 0.49083 (9) | 0.0244 (3) | |
H2B | 0.916 (4) | 0.5868 (15) | 0.4709 (13) | 0.036 (6)* | |
H2C | 0.799 (4) | 0.6132 (15) | 0.5370 (14) | 0.039 (6)* | |
C1 | 0.4652 (3) | 0.80545 (11) | 0.43571 (10) | 0.0221 (4) | |
C2 | 0.2549 (3) | 0.79903 (13) | 0.38618 (10) | 0.0261 (4) | |
H2A | 0.1664 | 0.7472 | 0.3815 | 0.031* | |
C3 | 0.1743 (4) | 0.86908 (14) | 0.34326 (11) | 0.0333 (5) | |
H3A | 0.0305 | 0.8654 | 0.3087 | 0.040* | |
C4 | 0.3046 (4) | 0.94449 (14) | 0.35096 (12) | 0.0365 (5) | |
H4A | 0.2497 | 0.9924 | 0.3215 | 0.044* | |
C5 | 0.5133 (4) | 0.95038 (13) | 0.40107 (12) | 0.0342 (5) | |
H5A | 0.6005 | 1.0025 | 0.4056 | 0.041* | |
C6 | 0.5995 (4) | 0.88092 (12) | 0.44550 (10) | 0.0260 (4) | |
C7 | 0.8218 (4) | 0.88805 (12) | 0.49865 (11) | 0.0297 (4) | |
H7A | 0.9445 | 0.9242 | 0.4844 | 0.036* | |
C8 | 0.8718 (4) | 0.84968 (12) | 0.56468 (11) | 0.0288 (4) | |
H8A | 1.0266 | 0.8608 | 0.5918 | 0.035* | |
C9 | 0.7130 (3) | 0.79217 (12) | 0.59973 (10) | 0.0237 (4) | |
C10 | 0.7161 (4) | 0.79098 (13) | 0.67723 (10) | 0.0294 (4) | |
H10A | 0.8281 | 0.8259 | 0.7076 | 0.035* | |
C11 | 0.5587 (4) | 0.73972 (13) | 0.70993 (10) | 0.0302 (4) | |
H11A | 0.5626 | 0.7402 | 0.7625 | 0.036* | |
C12 | 0.3952 (4) | 0.68761 (13) | 0.66703 (10) | 0.0278 (4) | |
H12A | 0.2854 | 0.6534 | 0.6899 | 0.033* | |
C13 | 0.3928 (3) | 0.68570 (12) | 0.59029 (10) | 0.0235 (4) | |
H13A | 0.2829 | 0.6496 | 0.5603 | 0.028* | |
C14 | 0.5517 (3) | 0.73682 (11) | 0.55793 (9) | 0.0205 (4) | |
C15 | 0.6949 (3) | 0.67510 (11) | 0.44989 (9) | 0.0197 (4) | |
S1 | 1.11791 (7) | 0.52090 (3) | 0.34676 (2) | 0.01901 (13) | |
O2 | 0.8898 (2) | 0.56267 (8) | 0.31431 (7) | 0.0261 (3) | |
O3 | 1.0868 (2) | 0.43046 (8) | 0.35405 (7) | 0.0289 (3) | |
O4 | 1.2186 (2) | 0.56268 (9) | 0.41551 (7) | 0.0278 (3) | |
C16 | 1.3180 (4) | 0.53606 (15) | 0.28087 (12) | 0.0344 (5) | |
H16A | 1.4767 | 0.5120 | 0.2998 | 0.052* | |
H16B | 1.3353 | 0.5971 | 0.2717 | 0.052* | |
H16C | 1.2540 | 0.5076 | 0.2343 | 0.052* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0302 (7) | 0.0229 (7) | 0.0155 (6) | 0.0044 (5) | 0.0041 (5) | 0.0004 (5) |
N1 | 0.0259 (8) | 0.0173 (7) | 0.0150 (7) | 0.0002 (6) | 0.0025 (6) | −0.0008 (6) |
N2 | 0.0309 (9) | 0.0258 (8) | 0.0163 (8) | 0.0070 (7) | 0.0026 (6) | −0.0002 (7) |
C1 | 0.0304 (10) | 0.0188 (9) | 0.0189 (9) | 0.0039 (7) | 0.0102 (7) | 0.0005 (7) |
C2 | 0.0276 (10) | 0.0311 (10) | 0.0210 (9) | 0.0047 (8) | 0.0082 (7) | 0.0020 (8) |
C3 | 0.0344 (11) | 0.0426 (13) | 0.0245 (10) | 0.0155 (9) | 0.0099 (8) | 0.0054 (9) |
C4 | 0.0508 (13) | 0.0317 (11) | 0.0302 (11) | 0.0186 (10) | 0.0173 (10) | 0.0101 (9) |
C5 | 0.0535 (13) | 0.0215 (10) | 0.0315 (11) | 0.0043 (9) | 0.0197 (10) | 0.0029 (8) |
C6 | 0.0365 (10) | 0.0212 (9) | 0.0227 (9) | 0.0029 (8) | 0.0130 (8) | −0.0002 (7) |
C7 | 0.0388 (11) | 0.0207 (9) | 0.0319 (11) | −0.0100 (8) | 0.0135 (9) | −0.0064 (8) |
C8 | 0.0316 (10) | 0.0252 (10) | 0.0296 (10) | −0.0077 (8) | 0.0043 (8) | −0.0072 (8) |
C9 | 0.0277 (10) | 0.0218 (9) | 0.0220 (9) | −0.0009 (7) | 0.0046 (7) | −0.0043 (7) |
C10 | 0.0374 (11) | 0.0287 (10) | 0.0215 (9) | −0.0026 (8) | 0.0018 (8) | −0.0089 (8) |
C11 | 0.0401 (11) | 0.0357 (11) | 0.0154 (9) | 0.0014 (9) | 0.0059 (8) | −0.0032 (8) |
C12 | 0.0307 (10) | 0.0324 (11) | 0.0219 (10) | −0.0007 (8) | 0.0088 (8) | 0.0003 (8) |
C13 | 0.0239 (9) | 0.0251 (10) | 0.0214 (9) | −0.0016 (7) | 0.0023 (7) | −0.0012 (7) |
C14 | 0.0247 (9) | 0.0211 (9) | 0.0155 (8) | 0.0033 (7) | 0.0023 (7) | −0.0020 (7) |
C15 | 0.0220 (8) | 0.0190 (9) | 0.0176 (8) | −0.0038 (7) | 0.0006 (7) | −0.0020 (7) |
S1 | 0.0188 (2) | 0.0212 (2) | 0.0170 (2) | 0.00055 (16) | 0.00206 (15) | −0.00143 (16) |
O2 | 0.0258 (7) | 0.0319 (7) | 0.0196 (6) | 0.0080 (5) | −0.0009 (5) | −0.0044 (5) |
O3 | 0.0359 (8) | 0.0240 (7) | 0.0257 (7) | −0.0002 (6) | 0.0006 (6) | 0.0002 (5) |
O4 | 0.0261 (7) | 0.0329 (8) | 0.0228 (7) | 0.0017 (6) | −0.0024 (5) | −0.0066 (6) |
C16 | 0.0296 (11) | 0.0449 (13) | 0.0308 (11) | −0.0090 (9) | 0.0114 (8) | −0.0047 (9) |
Geometric parameters (Å, º) top
O1—C15 | 1.299 (2) | C7—H7A | 0.9500 |
O1—H1A | 0.98 (3) | C8—C9 | 1.467 (3) |
N1—C15 | 1.338 (2) | C8—H8A | 0.9500 |
N1—C1 | 1.440 (2) | C9—C14 | 1.399 (2) |
N1—C14 | 1.441 (2) | C9—C10 | 1.403 (3) |
N2—C15 | 1.311 (2) | C10—C11 | 1.381 (3) |
N2—H2B | 0.86 (3) | C10—H10A | 0.9500 |
N2—H2C | 0.85 (3) | C11—C12 | 1.384 (3) |
C1—C2 | 1.381 (3) | C11—H11A | 0.9500 |
C1—C6 | 1.401 (3) | C12—C13 | 1.390 (3) |
C2—C3 | 1.388 (3) | C12—H12A | 0.9500 |
C2—H2A | 0.9500 | C13—C14 | 1.382 (3) |
C3—C4 | 1.387 (3) | C13—H13A | 0.9500 |
C3—H3A | 0.9500 | S1—O3 | 1.4404 (14) |
C4—C5 | 1.380 (3) | S1—O4 | 1.4534 (13) |
C4—H4A | 0.9500 | S1—O2 | 1.4803 (13) |
C5—C6 | 1.403 (3) | S1—C16 | 1.754 (2) |
C5—H5A | 0.9500 | C16—H16A | 0.9800 |
C6—C7 | 1.468 (3) | C16—H16B | 0.9800 |
C7—C8 | 1.336 (3) | C16—H16C | 0.9800 |
| | | |
C15—O1—H1A | 113.0 (16) | C14—C9—C8 | 121.97 (16) |
C15—N1—C1 | 120.41 (14) | C10—C9—C8 | 120.93 (17) |
C15—N1—C14 | 120.56 (14) | C11—C10—C9 | 120.90 (18) |
C1—N1—C14 | 116.77 (13) | C11—C10—H10A | 119.5 |
C15—N2—H2B | 116.6 (15) | C9—C10—H10A | 119.5 |
C15—N2—H2C | 119.4 (16) | C10—C11—C12 | 120.78 (17) |
H2B—N2—H2C | 123 (2) | C10—C11—H11A | 119.6 |
C2—C1—C6 | 122.42 (17) | C12—C11—H11A | 119.6 |
C2—C1—N1 | 120.11 (16) | C11—C12—C13 | 119.56 (18) |
C6—C1—N1 | 117.46 (16) | C11—C12—H12A | 120.2 |
C1—C2—C3 | 119.30 (19) | C13—C12—H12A | 120.2 |
C1—C2—H2A | 120.4 | C14—C13—C12 | 119.38 (17) |
C3—C2—H2A | 120.4 | C14—C13—H13A | 120.3 |
C4—C3—C2 | 119.7 (2) | C12—C13—H13A | 120.3 |
C4—C3—H3A | 120.1 | C13—C14—C9 | 122.21 (16) |
C2—C3—H3A | 120.1 | C13—C14—N1 | 119.58 (16) |
C5—C4—C3 | 120.47 (19) | C9—C14—N1 | 118.20 (15) |
C5—C4—H4A | 119.8 | O1—C15—N2 | 122.00 (16) |
C3—C4—H4A | 119.8 | O1—C15—N1 | 116.21 (15) |
C4—C5—C6 | 121.3 (2) | N2—C15—N1 | 121.78 (16) |
C4—C5—H5A | 119.4 | O3—S1—O4 | 113.88 (8) |
C6—C5—H5A | 119.4 | O3—S1—O2 | 111.52 (8) |
C1—C6—C5 | 116.78 (19) | O4—S1—O2 | 110.66 (8) |
C1—C6—C7 | 122.47 (17) | O3—S1—C16 | 106.95 (10) |
C5—C6—C7 | 120.75 (18) | O4—S1—C16 | 108.35 (9) |
C8—C7—C6 | 127.61 (18) | O2—S1—C16 | 104.96 (9) |
C8—C7—H7A | 116.2 | S1—C16—H16A | 109.5 |
C6—C7—H7A | 116.2 | S1—C16—H16B | 109.5 |
C7—C8—C9 | 126.90 (18) | H16A—C16—H16B | 109.5 |
C7—C8—H8A | 116.6 | S1—C16—H16C | 109.5 |
C9—C8—H8A | 116.6 | H16A—C16—H16C | 109.5 |
C14—C9—C10 | 117.10 (17) | H16B—C16—H16C | 109.5 |
| | | |
C15—N1—C1—C2 | 84.2 (2) | C14—C9—C10—C11 | −2.7 (3) |
C14—N1—C1—C2 | −112.73 (18) | C8—C9—C10—C11 | 176.96 (19) |
C15—N1—C1—C6 | −94.7 (2) | C9—C10—C11—C12 | 0.6 (3) |
C14—N1—C1—C6 | 68.3 (2) | C10—C11—C12—C13 | 1.2 (3) |
C6—C1—C2—C3 | 1.2 (3) | C11—C12—C13—C14 | −0.9 (3) |
N1—C1—C2—C3 | −177.70 (16) | C12—C13—C14—C9 | −1.3 (3) |
C1—C2—C3—C4 | −0.4 (3) | C12—C13—C14—N1 | 177.54 (16) |
C2—C3—C4—C5 | −0.1 (3) | C10—C9—C14—C13 | 3.0 (3) |
C3—C4—C5—C6 | −0.1 (3) | C8—C9—C14—C13 | −176.56 (18) |
C2—C1—C6—C5 | −1.4 (3) | C10—C9—C14—N1 | −175.83 (16) |
N1—C1—C6—C5 | 177.55 (15) | C8—C9—C14—N1 | 4.6 (3) |
C2—C1—C6—C7 | 179.41 (17) | C15—N1—C14—C13 | −86.7 (2) |
N1—C1—C6—C7 | −1.7 (3) | C1—N1—C14—C13 | 110.34 (19) |
C4—C5—C6—C1 | 0.8 (3) | C15—N1—C14—C9 | 92.3 (2) |
C4—C5—C6—C7 | −179.96 (18) | C1—N1—C14—C9 | −70.7 (2) |
C1—C6—C7—C8 | −34.2 (3) | C1—N1—C15—O1 | −9.3 (2) |
C5—C6—C7—C8 | 146.6 (2) | C14—N1—C15—O1 | −171.65 (15) |
C6—C7—C8—C9 | −0.9 (3) | C1—N1—C15—N2 | 169.74 (16) |
C7—C8—C9—C14 | 33.7 (3) | C14—N1—C15—N2 | 7.4 (3) |
C7—C8—C9—C10 | −145.9 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2 | 0.98 (3) | 1.53 (3) | 2.5004 (18) | 171 (3) |
N2—H2C···O3i | 0.85 (3) | 2.11 (3) | 2.885 (2) | 152 (2) |
N2—H2B···O4 | 0.86 (3) | 2.11 (3) | 2.924 (2) | 159 (2) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
(4) [(9,10-Dihydro-5
H-dibenzo[
b,
f]azepin-5-yl)(hydroxy)methylidene]azanium methanesulfonate
top
Crystal data top
C15H15N2O+·CH3O3S− | F(000) = 704 |
Mr = 334.38 | Dx = 1.410 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 5.4477 (2) Å | Cell parameters from 3424 reflections |
b = 15.7340 (7) Å | θ = 3.3–29.5° |
c = 18.5034 (8) Å | µ = 0.23 mm−1 |
β = 96.647 (4)° | T = 100 K |
V = 1575.34 (11) Å3 | Lath, colourless |
Z = 4 | 0.30 × 0.20 × 0.12 mm |
Data collection top
Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer | 3215 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 2783 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.021 |
Detector resolution: 10.5598 pixels mm-1 | θmax = 26.4°, θmin = 1.7° |
ω scans | h = −6→6 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | k = −19→18 |
Tmin = 0.766, Tmax = 1.000 | l = −23→22 |
7104 measured reflections | |
Refinement top
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.090 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0485P)2 + 0.7P] where P = (Fo2 + 2Fc2)/3 |
3215 reflections | (Δ/σ)max = 0.001 |
221 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.44 e Å−3 |
Special details top
Experimental. Absorption correction: CrysAlisPro, Agilent Technologies,
Version 1.171.35.8 (release 07-03-2011 CrysAlis171 .NET)
(compiled Mar 7 2011,18:06:32)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. Single-crystal X-ray data for structures (4), (5) and (6)
were measured at 100 K [270 K for structure (6)], on an Oxford
Diffraction (Agilent Technologies) SuperNova X-ray diffractometer equipped
with an Oxford Cryosystems Cobra low-temperature device using either
Mo Kα (λ = 0.71073 Å) radiation from a SuperNova Mo X-ray
microsource (Nova) for (4) or Cu Kα (λ = 1.54173 Å)
radiation from a SuperNova Cu X-ray microsource (Nova) for (5) and
(6) and focusing mirror optics (Agilent, 2011). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.73850 (19) | 0.67537 (7) | 0.37232 (5) | 0.0155 (2) | |
H1A | 0.816 (4) | 0.6288 (17) | 0.3548 (14) | 0.056 (7)* | |
N1 | 0.5897 (2) | 0.73580 (8) | 0.46781 (6) | 0.0129 (3) | |
N2 | 0.8547 (2) | 0.62104 (8) | 0.48580 (7) | 0.0159 (3) | |
H2B | 0.959 (3) | 0.5867 (12) | 0.4689 (10) | 0.019 (4)* | |
H2C | 0.848 (3) | 0.6210 (11) | 0.5304 (11) | 0.017 (4)* | |
C1 | 0.4756 (3) | 0.80112 (10) | 0.42031 (8) | 0.0141 (3) | |
C2 | 0.2727 (3) | 0.77834 (10) | 0.37107 (8) | 0.0162 (3) | |
H2A | 0.2165 | 0.7211 | 0.3687 | 0.019* | |
C3 | 0.1533 (3) | 0.83903 (10) | 0.32569 (8) | 0.0187 (3) | |
H3A | 0.0153 | 0.8238 | 0.2920 | 0.022* | |
C4 | 0.2370 (3) | 0.92249 (10) | 0.32975 (8) | 0.0194 (3) | |
H4A | 0.1570 | 0.9646 | 0.2986 | 0.023* | |
C5 | 0.4381 (3) | 0.94424 (10) | 0.37942 (8) | 0.0173 (3) | |
H5A | 0.4923 | 1.0017 | 0.3819 | 0.021* | |
C7 | 0.7832 (3) | 0.91600 (10) | 0.47730 (8) | 0.0167 (3) | |
H7A | 0.7252 | 0.9644 | 0.5050 | 0.020* | |
H7B | 0.9061 | 0.9389 | 0.4470 | 0.020* | |
C8 | 0.9199 (3) | 0.85443 (10) | 0.53251 (8) | 0.0182 (3) | |
H8A | 1.0093 | 0.8120 | 0.5059 | 0.022* | |
H8B | 1.0443 | 0.8867 | 0.5648 | 0.022* | |
C6 | 0.5634 (3) | 0.88445 (9) | 0.42593 (8) | 0.0140 (3) | |
C9 | 0.7518 (3) | 0.80844 (10) | 0.57854 (8) | 0.0158 (3) | |
C10 | 0.7465 (3) | 0.82293 (10) | 0.65272 (8) | 0.0203 (3) | |
H10A | 0.8565 | 0.8631 | 0.6774 | 0.024* | |
C11 | 0.5815 (3) | 0.77906 (10) | 0.69067 (8) | 0.0219 (3) | |
H11A | 0.5794 | 0.7896 | 0.7411 | 0.026* | |
C12 | 0.4196 (3) | 0.72000 (10) | 0.65603 (8) | 0.0195 (3) | |
H12A | 0.3063 | 0.6908 | 0.6825 | 0.023* | |
C13 | 0.4238 (3) | 0.70375 (10) | 0.58226 (8) | 0.0162 (3) | |
H13A | 0.3159 | 0.6628 | 0.5579 | 0.019* | |
C14 | 0.5882 (3) | 0.74844 (9) | 0.54505 (8) | 0.0137 (3) | |
C15 | 0.7298 (2) | 0.67538 (9) | 0.44226 (8) | 0.0129 (3) | |
S1 | 1.14613 (6) | 0.50621 (2) | 0.351758 (19) | 0.01365 (11) | |
O2 | 0.95704 (19) | 0.56144 (7) | 0.31122 (5) | 0.0181 (2) | |
O3 | 1.0521 (2) | 0.42143 (7) | 0.36193 (6) | 0.0201 (2) | |
O4 | 1.25031 (19) | 0.54714 (7) | 0.41908 (6) | 0.0203 (2) | |
C16 | 1.3818 (3) | 0.49719 (11) | 0.29503 (9) | 0.0213 (3) | |
H16A | 1.5215 | 0.4660 | 0.3205 | 0.032* | |
H16B | 1.4364 | 0.5540 | 0.2823 | 0.032* | |
H16C | 1.3190 | 0.4666 | 0.2506 | 0.032* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0183 (5) | 0.0182 (5) | 0.0099 (5) | 0.0029 (4) | 0.0014 (4) | −0.0011 (4) |
N1 | 0.0144 (6) | 0.0143 (6) | 0.0097 (6) | 0.0004 (5) | 0.0005 (5) | −0.0005 (5) |
N2 | 0.0192 (6) | 0.0185 (7) | 0.0099 (6) | 0.0047 (5) | 0.0011 (5) | 0.0000 (5) |
C1 | 0.0142 (7) | 0.0177 (7) | 0.0109 (7) | 0.0028 (6) | 0.0038 (5) | 0.0010 (6) |
C2 | 0.0139 (7) | 0.0200 (8) | 0.0150 (7) | −0.0011 (6) | 0.0026 (6) | −0.0010 (6) |
C3 | 0.0153 (7) | 0.0285 (9) | 0.0122 (7) | 0.0020 (6) | 0.0002 (6) | 0.0002 (6) |
C4 | 0.0203 (7) | 0.0249 (8) | 0.0136 (7) | 0.0077 (6) | 0.0037 (6) | 0.0049 (6) |
C5 | 0.0212 (7) | 0.0169 (7) | 0.0151 (7) | 0.0015 (6) | 0.0070 (6) | 0.0021 (6) |
C7 | 0.0184 (7) | 0.0163 (7) | 0.0155 (7) | −0.0030 (6) | 0.0026 (6) | −0.0003 (6) |
C8 | 0.0153 (7) | 0.0211 (8) | 0.0174 (7) | −0.0029 (6) | −0.0011 (6) | −0.0015 (6) |
C6 | 0.0145 (7) | 0.0175 (7) | 0.0108 (7) | 0.0012 (6) | 0.0050 (5) | −0.0003 (6) |
C9 | 0.0152 (7) | 0.0167 (7) | 0.0148 (7) | 0.0026 (6) | −0.0010 (6) | 0.0010 (6) |
C10 | 0.0246 (8) | 0.0187 (8) | 0.0162 (8) | 0.0014 (6) | −0.0035 (6) | −0.0023 (6) |
C11 | 0.0315 (8) | 0.0230 (8) | 0.0114 (7) | 0.0067 (7) | 0.0024 (6) | −0.0005 (6) |
C12 | 0.0214 (7) | 0.0230 (8) | 0.0151 (7) | 0.0048 (6) | 0.0068 (6) | 0.0042 (6) |
C13 | 0.0149 (7) | 0.0168 (7) | 0.0164 (7) | 0.0012 (6) | −0.0001 (6) | 0.0013 (6) |
C14 | 0.0146 (7) | 0.0156 (7) | 0.0109 (7) | 0.0043 (6) | 0.0009 (5) | 0.0001 (5) |
C15 | 0.0120 (6) | 0.0139 (7) | 0.0126 (7) | −0.0032 (5) | 0.0006 (5) | −0.0010 (5) |
S1 | 0.01256 (18) | 0.0164 (2) | 0.01192 (19) | 0.00119 (13) | 0.00112 (14) | −0.00096 (13) |
O2 | 0.0180 (5) | 0.0222 (6) | 0.0136 (5) | 0.0051 (4) | −0.0008 (4) | −0.0021 (4) |
O3 | 0.0220 (5) | 0.0204 (6) | 0.0179 (5) | −0.0028 (4) | 0.0023 (4) | 0.0019 (4) |
O4 | 0.0183 (5) | 0.0247 (6) | 0.0169 (5) | 0.0033 (4) | −0.0028 (4) | −0.0040 (5) |
C16 | 0.0162 (7) | 0.0262 (9) | 0.0227 (8) | −0.0004 (6) | 0.0078 (6) | −0.0010 (7) |
Geometric parameters (Å, º) top
O1—C15 | 1.3005 (17) | C7—H7B | 0.9900 |
O1—H1A | 0.92 (3) | C8—C9 | 1.506 (2) |
N1—C15 | 1.3390 (19) | C8—H8A | 0.9900 |
N1—C14 | 1.4440 (18) | C8—H8B | 0.9900 |
N1—C1 | 1.4452 (18) | C9—C14 | 1.394 (2) |
N2—C15 | 1.3101 (19) | C9—C10 | 1.395 (2) |
N2—H2B | 0.87 (2) | C10—C11 | 1.387 (2) |
N2—H2C | 0.830 (19) | C10—H10A | 0.9500 |
C1—C2 | 1.395 (2) | C11—C12 | 1.386 (2) |
C1—C6 | 1.396 (2) | C11—H11A | 0.9500 |
C2—C3 | 1.383 (2) | C12—C13 | 1.392 (2) |
C2—H2A | 0.9500 | C12—H12A | 0.9500 |
C3—C4 | 1.389 (2) | C13—C14 | 1.383 (2) |
C3—H3A | 0.9500 | C13—H13A | 0.9500 |
C4—C5 | 1.389 (2) | S1—O3 | 1.4489 (11) |
C4—H4A | 0.9500 | S1—O4 | 1.4578 (11) |
C5—C6 | 1.399 (2) | S1—O2 | 1.4833 (11) |
C5—H5A | 0.9500 | S1—C16 | 1.7556 (15) |
C7—C6 | 1.523 (2) | C16—H16A | 0.9800 |
C7—C8 | 1.536 (2) | C16—H16B | 0.9800 |
C7—H7A | 0.9900 | C16—H16C | 0.9800 |
| | | |
C15—O1—H1A | 114.8 (16) | C1—C6—C7 | 126.21 (13) |
C15—N1—C14 | 121.07 (12) | C5—C6—C7 | 117.22 (13) |
C15—N1—C1 | 120.84 (12) | C14—C9—C10 | 117.59 (14) |
C14—N1—C1 | 116.91 (11) | C14—C9—C8 | 118.27 (13) |
C15—N2—H2B | 119.9 (12) | C10—C9—C8 | 124.13 (14) |
C15—N2—H2C | 122.2 (12) | C11—C10—C9 | 120.35 (14) |
H2B—N2—H2C | 117.6 (17) | C11—C10—H10A | 119.8 |
C2—C1—C6 | 121.93 (14) | C9—C10—H10A | 119.8 |
C2—C1—N1 | 117.83 (13) | C12—C11—C10 | 120.98 (14) |
C6—C1—N1 | 120.21 (13) | C12—C11—H11A | 119.5 |
C3—C2—C1 | 120.02 (14) | C10—C11—H11A | 119.5 |
C3—C2—H2A | 120.0 | C11—C12—C13 | 119.65 (14) |
C1—C2—H2A | 120.0 | C11—C12—H12A | 120.2 |
C2—C3—C4 | 119.42 (14) | C13—C12—H12A | 120.2 |
C2—C3—H3A | 120.3 | C14—C13—C12 | 118.68 (14) |
C4—C3—H3A | 120.3 | C14—C13—H13A | 120.7 |
C5—C4—C3 | 119.85 (14) | C12—C13—H13A | 120.7 |
C5—C4—H4A | 120.1 | C13—C14—C9 | 122.75 (13) |
C3—C4—H4A | 120.1 | C13—C14—N1 | 120.05 (13) |
C4—C5—C6 | 122.21 (14) | C9—C14—N1 | 117.17 (13) |
C4—C5—H5A | 118.9 | O1—C15—N2 | 122.38 (13) |
C6—C5—H5A | 118.9 | O1—C15—N1 | 116.06 (13) |
C6—C7—C8 | 119.66 (13) | N2—C15—N1 | 121.53 (13) |
C6—C7—H7A | 107.4 | O3—S1—O4 | 113.84 (7) |
C8—C7—H7A | 107.4 | O3—S1—O2 | 111.70 (6) |
C6—C7—H7B | 107.4 | O4—S1—O2 | 110.63 (6) |
C8—C7—H7B | 107.4 | O3—S1—C16 | 107.30 (7) |
H7A—C7—H7B | 106.9 | O4—S1—C16 | 107.90 (7) |
C9—C8—C7 | 113.54 (12) | O2—S1—C16 | 104.95 (7) |
C9—C8—H8A | 108.9 | S1—C16—H16A | 109.5 |
C7—C8—H8A | 108.9 | S1—C16—H16B | 109.5 |
C9—C8—H8B | 108.9 | H16A—C16—H16B | 109.5 |
C7—C8—H8B | 108.9 | S1—C16—H16C | 109.5 |
H8A—C8—H8B | 107.7 | H16A—C16—H16C | 109.5 |
C1—C6—C5 | 116.57 (13) | H16B—C16—H16C | 109.5 |
| | | |
C15—N1—C1—C2 | 73.83 (17) | C14—C9—C10—C11 | −0.5 (2) |
C14—N1—C1—C2 | −118.42 (14) | C8—C9—C10—C11 | 178.48 (14) |
C15—N1—C1—C6 | −108.14 (16) | C9—C10—C11—C12 | 0.2 (2) |
C14—N1—C1—C6 | 59.61 (17) | C10—C11—C12—C13 | 0.6 (2) |
C6—C1—C2—C3 | 0.4 (2) | C11—C12—C13—C14 | −1.1 (2) |
N1—C1—C2—C3 | 178.40 (13) | C12—C13—C14—C9 | 0.7 (2) |
C1—C2—C3—C4 | −0.1 (2) | C12—C13—C14—N1 | −177.29 (13) |
C2—C3—C4—C5 | −0.4 (2) | C10—C9—C14—C13 | 0.1 (2) |
C3—C4—C5—C6 | 0.6 (2) | C8—C9—C14—C13 | −179.01 (13) |
C6—C7—C8—C9 | −52.33 (18) | C10—C9—C14—N1 | 178.13 (13) |
C2—C1—C6—C5 | −0.2 (2) | C8—C9—C14—N1 | −0.93 (19) |
N1—C1—C6—C5 | −178.17 (12) | C15—N1—C14—C13 | −88.80 (17) |
C2—C1—C6—C7 | −179.67 (13) | C1—N1—C14—C13 | 103.48 (15) |
N1—C1—C6—C7 | 2.4 (2) | C15—N1—C14—C9 | 93.07 (16) |
C4—C5—C6—C1 | −0.3 (2) | C1—N1—C14—C9 | −74.65 (16) |
C4—C5—C6—C7 | 179.23 (13) | C14—N1—C15—O1 | −172.74 (12) |
C8—C7—C6—C1 | −3.8 (2) | C1—N1—C15—O1 | −5.50 (19) |
C8—C7—C6—C5 | 176.77 (13) | C14—N1—C15—N2 | 5.7 (2) |
C7—C8—C9—C14 | 68.68 (18) | C1—N1—C15—N2 | 172.91 (13) |
C7—C8—C9—C10 | −110.31 (16) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2 | 0.92 (3) | 1.58 (3) | 2.4941 (15) | 168 (2) |
N2—H2C···O3i | 0.830 (19) | 2.112 (19) | 2.8830 (17) | 154.4 (17) |
N2—H2B···O4 | 0.87 (2) | 2.02 (2) | 2.8523 (17) | 159.5 (17) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
(5) Dibenzo[
b,
f]azepine-5-carboxamide–trifluoroacetic acid (1/1)
top
Crystal data top
C15H12N2O·C2HF3O2 | F(000) = 720 |
Mr = 350.29 | Dx = 1.493 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54178 Å |
a = 14.9968 (12) Å | Cell parameters from 3607 reflections |
b = 5.2660 (3) Å | θ = 3.0–75.6° |
c = 20.1911 (12) Å | µ = 1.10 mm−1 |
β = 102.191 (7)° | T = 100 K |
V = 1558.60 (18) Å3 | Lath, colourless |
Z = 4 | 0.45 × 0.20 × 0.10 mm |
Data collection top
SuperNova, Dual, Cu at zero, Atlas diffractometer | 3189 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 2937 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.030 |
Detector resolution: 10.5598 pixels mm-1 | θmax = 74.5°, θmin = 3.4° |
ω scans | h = −18→18 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | k = −3→6 |
Tmin = 0.650, Tmax = 1.000 | l = −25→25 |
7053 measured reflections | |
Refinement top
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0945P)2 + 0.550P] where P = (Fo2 + 2Fc2)/3 |
3189 reflections | (Δ/σ)max = 0.001 |
266 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
Special details top
Experimental. Absorption correction: CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. Single-crystal X-ray data for structures (4), (5) and (6)
were measured at 100 K [270 K for structure (6)], on an Oxford
Diffraction (Agilent Technologies) SuperNova X-ray diffractometer equipped
with an Oxford Cryosystems Cobra low-temperature device using either
Mo Kα (λ = 0.71073 Å) radiation from a SuperNova Mo X-ray
microsource (Nova) for (4) or Cu Kα (λ = 1.54173 Å)
radiation from a SuperNova Cu X-ray microsource (Nova) for (5) and
(6) and focusing mirror optics (Agilent, 2011). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
N1 | 1.01040 (8) | 0.3899 (2) | −0.19315 (5) | 0.0204 (3) | |
N2 | 1.13634 (9) | 0.1950 (3) | −0.22083 (6) | 0.0247 (3) | |
H2B | 1.1857 (14) | 0.109 (4) | −0.2068 (10) | 0.029 (5)* | |
H2C | 1.1209 (13) | 0.258 (4) | −0.2615 (11) | 0.030 (5)* | |
O1 | 1.11508 (7) | 0.1982 (2) | −0.11242 (5) | 0.0244 (2) | |
C1 | 0.95601 (9) | 0.4422 (3) | −0.14367 (6) | 0.0197 (3) | |
C2 | 0.97975 (10) | 0.6438 (3) | −0.09929 (7) | 0.0230 (3) | |
H2A | 1.0290 | 0.7522 | −0.1033 | 0.028* | |
C3 | 0.93124 (10) | 0.6866 (3) | −0.04891 (7) | 0.0249 (3) | |
H3A | 0.9468 | 0.8254 | −0.0186 | 0.030* | |
C4 | 0.85989 (10) | 0.5256 (3) | −0.04289 (7) | 0.0256 (3) | |
H4A | 0.8276 | 0.5520 | −0.0078 | 0.031* | |
C5 | 0.83597 (9) | 0.3273 (3) | −0.08796 (7) | 0.0243 (3) | |
H5A | 0.7872 | 0.2182 | −0.0833 | 0.029* | |
C6 | 0.88225 (9) | 0.2835 (3) | −0.14061 (7) | 0.0208 (3) | |
C7 | 0.85101 (9) | 0.0800 (3) | −0.18921 (7) | 0.0232 (3) | |
H7A | 0.8226 | −0.0608 | −0.1727 | 0.028* | |
C8 | 0.85782 (9) | 0.0688 (3) | −0.25451 (7) | 0.0233 (3) | |
H8A | 0.8345 | −0.0801 | −0.2786 | 0.028* | |
C9 | 0.89710 (9) | 0.2598 (3) | −0.29261 (7) | 0.0215 (3) | |
C10 | 0.86126 (10) | 0.2862 (3) | −0.36231 (7) | 0.0248 (3) | |
H10A | 0.8153 | 0.1720 | −0.3841 | 0.030* | |
C11 | 0.89142 (10) | 0.4749 (3) | −0.40005 (7) | 0.0266 (3) | |
H11A | 0.8658 | 0.4899 | −0.4471 | 0.032* | |
C12 | 0.95892 (10) | 0.6419 (3) | −0.36917 (7) | 0.0269 (3) | |
H12A | 0.9787 | 0.7735 | −0.3949 | 0.032* | |
C13 | 0.99757 (10) | 0.6168 (3) | −0.30068 (7) | 0.0242 (3) | |
H13A | 1.0442 | 0.7300 | −0.2794 | 0.029* | |
C14 | 0.96744 (9) | 0.4245 (3) | −0.26327 (6) | 0.0204 (3) | |
C15 | 1.08910 (9) | 0.2580 (3) | −0.17442 (7) | 0.0204 (3) | |
O2 | 1.23590 (7) | −0.1025 (2) | −0.06761 (5) | 0.0278 (3) | |
H2D | 1.1757 (19) | 0.053 (6) | −0.0964 (13) | 0.067 (8)* | |
O3 | 1.28746 (8) | −0.1351 (3) | −0.16402 (6) | 0.0371 (3) | |
C16 | 1.28569 (10) | −0.1916 (3) | −0.10585 (7) | 0.0253 (3) | |
C17A | 1.35264 (11) | −0.3987 (3) | −0.07195 (8) | 0.0311 (4) | 0.738 (15) |
F1A | 1.3372 (3) | −0.4807 (8) | −0.01191 (14) | 0.0412 (7) | 0.738 (15) |
F2A | 1.34620 (19) | −0.6059 (4) | −0.11052 (17) | 0.0452 (8) | 0.738 (15) |
F3A | 1.4373 (2) | −0.3211 (7) | −0.0597 (3) | 0.0433 (8) | 0.738 (15) |
C17B | 1.35264 (11) | −0.3987 (3) | −0.07195 (8) | 0.0311 (4) | 0.262 (15) |
F1B | 1.3244 (10) | −0.536 (3) | −0.0352 (13) | 0.084 (5) | 0.262 (15) |
F2B | 1.3867 (17) | −0.507 (5) | −0.1213 (4) | 0.109 (9) | 0.262 (15) |
F3B | 1.4281 (7) | −0.257 (3) | −0.0392 (8) | 0.060 (3) | 0.262 (15) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0196 (5) | 0.0241 (6) | 0.0183 (5) | 0.0002 (4) | 0.0055 (4) | 0.0007 (4) |
N2 | 0.0222 (6) | 0.0325 (6) | 0.0202 (6) | 0.0037 (5) | 0.0064 (5) | 0.0020 (5) |
O1 | 0.0245 (5) | 0.0302 (5) | 0.0189 (5) | 0.0061 (4) | 0.0057 (4) | 0.0013 (4) |
C1 | 0.0203 (6) | 0.0212 (6) | 0.0178 (6) | 0.0035 (5) | 0.0048 (5) | 0.0035 (5) |
C2 | 0.0255 (7) | 0.0220 (6) | 0.0210 (6) | −0.0005 (5) | 0.0035 (5) | 0.0021 (5) |
C3 | 0.0298 (7) | 0.0244 (7) | 0.0196 (6) | 0.0051 (6) | 0.0028 (5) | −0.0011 (5) |
C4 | 0.0241 (6) | 0.0337 (7) | 0.0198 (6) | 0.0082 (6) | 0.0066 (5) | 0.0018 (5) |
C5 | 0.0201 (6) | 0.0307 (7) | 0.0227 (6) | 0.0020 (5) | 0.0057 (5) | 0.0045 (5) |
C6 | 0.0207 (6) | 0.0213 (6) | 0.0203 (6) | 0.0036 (5) | 0.0042 (5) | 0.0038 (5) |
C7 | 0.0209 (6) | 0.0219 (6) | 0.0273 (7) | −0.0015 (5) | 0.0060 (5) | 0.0033 (5) |
C8 | 0.0222 (6) | 0.0211 (6) | 0.0259 (7) | −0.0022 (5) | 0.0035 (5) | −0.0019 (5) |
C9 | 0.0223 (6) | 0.0207 (6) | 0.0220 (6) | 0.0024 (5) | 0.0063 (5) | −0.0009 (5) |
C10 | 0.0228 (7) | 0.0291 (7) | 0.0225 (6) | 0.0014 (6) | 0.0045 (5) | −0.0036 (5) |
C11 | 0.0276 (7) | 0.0339 (8) | 0.0183 (6) | 0.0056 (6) | 0.0048 (5) | 0.0019 (5) |
C12 | 0.0307 (7) | 0.0275 (7) | 0.0242 (7) | 0.0024 (6) | 0.0099 (6) | 0.0048 (5) |
C13 | 0.0257 (7) | 0.0239 (7) | 0.0240 (7) | −0.0009 (5) | 0.0073 (5) | 0.0000 (5) |
C14 | 0.0213 (6) | 0.0215 (6) | 0.0193 (6) | 0.0028 (5) | 0.0062 (5) | 0.0001 (5) |
C15 | 0.0204 (6) | 0.0206 (6) | 0.0208 (6) | −0.0030 (5) | 0.0053 (5) | −0.0013 (5) |
O2 | 0.0280 (5) | 0.0332 (6) | 0.0238 (5) | 0.0095 (4) | 0.0094 (4) | 0.0020 (4) |
O3 | 0.0386 (6) | 0.0493 (7) | 0.0260 (5) | 0.0165 (5) | 0.0129 (5) | 0.0021 (5) |
C16 | 0.0240 (7) | 0.0279 (7) | 0.0246 (7) | 0.0026 (6) | 0.0061 (5) | −0.0040 (5) |
C17A | 0.0282 (7) | 0.0329 (8) | 0.0335 (8) | 0.0054 (6) | 0.0091 (6) | −0.0017 (6) |
F1A | 0.0432 (14) | 0.0448 (14) | 0.0396 (12) | 0.0211 (11) | 0.0180 (9) | 0.0185 (8) |
F2A | 0.0524 (13) | 0.0290 (10) | 0.0523 (12) | 0.0110 (9) | 0.0066 (8) | −0.0112 (7) |
F3A | 0.0210 (8) | 0.0354 (13) | 0.0723 (19) | 0.0016 (8) | 0.0071 (10) | 0.0129 (11) |
C17B | 0.0282 (7) | 0.0329 (8) | 0.0335 (8) | 0.0054 (6) | 0.0091 (6) | −0.0017 (6) |
F1B | 0.056 (5) | 0.059 (7) | 0.141 (13) | 0.012 (5) | 0.032 (8) | 0.063 (8) |
F2B | 0.139 (14) | 0.134 (14) | 0.049 (3) | 0.117 (13) | 0.009 (5) | −0.008 (5) |
F3B | 0.036 (3) | 0.068 (5) | 0.067 (6) | 0.019 (3) | −0.007 (3) | 0.011 (4) |
Geometric parameters (Å, º) top
N1—C15 | 1.3529 (18) | C7—H7A | 0.9500 |
N1—C14 | 1.4380 (16) | C8—C9 | 1.4636 (19) |
N1—C1 | 1.4433 (16) | C8—H8A | 0.9500 |
N2—C15 | 1.3306 (18) | C9—C14 | 1.3971 (19) |
N2—H2B | 0.86 (2) | C9—C10 | 1.4034 (19) |
N2—H2C | 0.87 (2) | C10—C11 | 1.385 (2) |
O1—C15 | 1.2696 (17) | C10—H10A | 0.9500 |
O1—H2D | 1.18 (3) | C11—C12 | 1.386 (2) |
C1—C2 | 1.3865 (19) | C11—H11A | 0.9500 |
C1—C6 | 1.3980 (19) | C12—C13 | 1.388 (2) |
C2—C3 | 1.388 (2) | C12—H12A | 0.9500 |
C2—H2A | 0.9500 | C13—C14 | 1.3944 (19) |
C3—C4 | 1.390 (2) | C13—H13A | 0.9500 |
C3—H3A | 0.9500 | O2—C16 | 1.2718 (18) |
C4—C5 | 1.382 (2) | O2—H2D | 1.27 (3) |
C4—H4A | 0.9500 | O3—C16 | 1.2174 (19) |
C5—C6 | 1.4059 (19) | C16—C17A | 1.541 (2) |
C5—H5A | 0.9500 | C17A—F3A | 1.306 (3) |
C6—C7 | 1.4618 (19) | C17A—F2A | 1.332 (3) |
C7—C8 | 1.345 (2) | C17A—F1A | 1.352 (4) |
| | | |
C15—N1—C14 | 121.55 (11) | C14—C9—C10 | 117.30 (12) |
C15—N1—C1 | 119.45 (11) | C14—C9—C8 | 123.75 (12) |
C14—N1—C1 | 117.14 (10) | C10—C9—C8 | 118.92 (12) |
C15—N2—H2B | 116.5 (13) | C11—C10—C9 | 121.48 (13) |
C15—N2—H2C | 119.6 (13) | C11—C10—H10A | 119.3 |
H2B—N2—H2C | 123.3 (18) | C9—C10—H10A | 119.3 |
C15—O1—H2D | 119.3 (13) | C10—C11—C12 | 120.01 (13) |
C2—C1—C6 | 121.78 (12) | C10—C11—H11A | 120.0 |
C2—C1—N1 | 119.21 (12) | C12—C11—H11A | 120.0 |
C6—C1—N1 | 118.99 (12) | C11—C12—C13 | 119.97 (13) |
C1—C2—C3 | 119.67 (13) | C11—C12—H12A | 120.0 |
C1—C2—H2A | 120.2 | C13—C12—H12A | 120.0 |
C3—C2—H2A | 120.2 | C12—C13—C14 | 119.59 (13) |
C2—C3—C4 | 119.82 (13) | C12—C13—H13A | 120.2 |
C2—C3—H3A | 120.1 | C14—C13—H13A | 120.2 |
C4—C3—H3A | 120.1 | C13—C14—C9 | 121.55 (12) |
C5—C4—C3 | 120.05 (13) | C13—C14—N1 | 119.75 (12) |
C5—C4—H4A | 120.0 | C9—C14—N1 | 118.68 (12) |
C3—C4—H4A | 120.0 | O1—C15—N2 | 122.30 (13) |
C4—C5—C6 | 121.39 (13) | O1—C15—N1 | 118.10 (12) |
C4—C5—H5A | 119.3 | N2—C15—N1 | 119.60 (12) |
C6—C5—H5A | 119.3 | C16—O2—H2D | 114.4 (12) |
C1—C6—C5 | 117.20 (13) | O3—C16—O2 | 129.11 (14) |
C1—C6—C7 | 123.57 (12) | O3—C16—C17A | 117.16 (13) |
C5—C6—C7 | 119.23 (12) | O2—C16—C17A | 113.73 (12) |
C8—C7—C6 | 127.61 (13) | F3A—C17A—F2A | 108.4 (2) |
C8—C7—H7A | 116.2 | F3A—C17A—F1A | 105.9 (3) |
C6—C7—H7A | 116.2 | F2A—C17A—F1A | 104.9 (2) |
C7—C8—C9 | 127.39 (13) | F3A—C17A—C16 | 112.24 (19) |
C7—C8—H8A | 116.3 | F2A—C17A—C16 | 111.09 (16) |
C9—C8—H8A | 116.3 | F1A—C17A—C16 | 113.91 (19) |
| | | |
C15—N1—C1—C2 | 81.15 (16) | C10—C11—C12—C13 | 1.3 (2) |
C14—N1—C1—C2 | −114.12 (14) | C11—C12—C13—C14 | −0.6 (2) |
C15—N1—C1—C6 | −97.09 (15) | C12—C13—C14—C9 | −1.9 (2) |
C14—N1—C1—C6 | 67.64 (16) | C12—C13—C14—N1 | 176.91 (12) |
C6—C1—C2—C3 | 2.0 (2) | C10—C9—C14—C13 | 3.5 (2) |
N1—C1—C2—C3 | −176.17 (12) | C8—C9—C14—C13 | −174.75 (13) |
C1—C2—C3—C4 | 0.6 (2) | C10—C9—C14—N1 | −175.30 (11) |
C2—C3—C4—C5 | −1.5 (2) | C8—C9—C14—N1 | 6.4 (2) |
C3—C4—C5—C6 | −0.2 (2) | C15—N1—C14—C13 | −82.35 (17) |
C2—C1—C6—C5 | −3.64 (19) | C1—N1—C14—C13 | 113.26 (14) |
N1—C1—C6—C5 | 174.56 (11) | C15—N1—C14—C9 | 96.48 (15) |
C2—C1—C6—C7 | 175.64 (12) | C1—N1—C14—C9 | −67.91 (16) |
N1—C1—C6—C7 | −6.17 (19) | C14—N1—C15—O1 | −168.32 (12) |
C4—C5—C6—C1 | 2.7 (2) | C1—N1—C15—O1 | −4.28 (19) |
C4—C5—C6—C7 | −176.59 (12) | C14—N1—C15—N2 | 11.6 (2) |
C1—C6—C7—C8 | −28.7 (2) | C1—N1—C15—N2 | 175.60 (12) |
C5—C6—C7—C8 | 150.59 (15) | O3—C16—C17A—F3A | 69.8 (3) |
C6—C7—C8—C9 | −0.9 (2) | O2—C16—C17A—F3A | −109.9 (3) |
C7—C8—C9—C14 | 29.8 (2) | O3—C16—C17A—F2A | −51.7 (3) |
C7—C8—C9—C10 | −148.46 (15) | O2—C16—C17A—F2A | 128.6 (2) |
C14—C9—C10—C11 | −2.8 (2) | O3—C16—C17A—F1A | −169.9 (2) |
C8—C9—C10—C11 | 175.55 (13) | O2—C16—C17A—F1A | 10.4 (3) |
C9—C10—C11—C12 | 0.5 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···O3 | 0.86 (2) | 2.04 (2) | 2.8941 (18) | 169.1 (18) |
N2—H2C···O3i | 0.87 (2) | 2.31 (2) | 2.9383 (16) | 129.1 (16) |
O1—H2D···O2 | 1.18 (3) | 1.27 (3) | 2.4322 (14) | 168 (2) |
O1—H2D···O3 | 1.18 (3) | 2.57 (3) | 3.4622 (15) | 130.9 (17) |
Symmetry code: (i) −x+5/2, y+1/2, −z−1/2. |
(6) Dibenzo[
b,
f]azepine-5-carboxamide–trifluoroacetic acid (1/1)
top
Crystal data top
C15H12N2O·C2HF3O2 | F(000) = 720 |
Mr = 350.29 | Dx = 1.442 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54178 Å |
a = 14.9970 (3) Å | Cell parameters from 3984 reflections |
b = 5.3712 (1) Å | θ = 3.0–75.8° |
c = 20.4441 (4) Å | µ = 1.06 mm−1 |
β = 101.529 (2)° | T = 270 K |
V = 1613.58 (5) Å3 | Lath, colourless |
Z = 4 | 0.45 × 0.25 × 0.18 mm |
Data collection top
SuperNova, Dual, Cu at zero, Atlas diffractometer | 3302 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 2957 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.021 |
Detector resolution: 10.5598 pixels mm-1 | θmax = 74.5°, θmin = 3.4° |
ω scans | h = −18→17 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | k = −4→6 |
Tmin = 0.738, Tmax = 1.000 | l = −24→25 |
7096 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.050 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.155 | w = 1/[σ2(Fo2) + (0.0975P)2 + 0.320P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
3302 reflections | Δρmax = 0.34 e Å−3 |
267 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0047 (7) |
Special details top
Experimental. CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. Single-crystal X-ray data for structures (4), (5) and (6)
were measured at 100 K [270 K for structure (6)], on an Oxford
Diffraction (Agilent Technologies) SuperNova X-ray diffractometer equipped
with an Oxford Cryosystems Cobra low-temperature device using either
Mo Kα (λ = 0.71073 Å) radiation from a SuperNova Mo X-ray
microsource (Nova) for (4) or Cu Kα (λ = 1.54173 Å)
radiation from a SuperNova Cu X-ray microsource (Nova) for (5) and
(6) and focusing mirror optics (Agilent, 2011). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
N1 | 1.00960 (8) | 0.3794 (2) | −0.19199 (6) | 0.0445 (3) | |
N2 | 1.13368 (10) | 0.1840 (3) | −0.22070 (7) | 0.0594 (4) | |
H2B | 1.1836 (16) | 0.095 (4) | −0.2079 (10) | 0.061 (5)* | |
H2C | 1.1187 (15) | 0.251 (4) | −0.2610 (12) | 0.068 (6)* | |
O1 | 1.11367 (8) | 0.1877 (2) | −0.11365 (5) | 0.0561 (3) | |
C1 | 0.95582 (9) | 0.4336 (3) | −0.14274 (7) | 0.0438 (3) | |
C2 | 0.97930 (12) | 0.6319 (3) | −0.09996 (8) | 0.0541 (4) | |
H2A | 1.0276 | 0.7349 | −0.1044 | 0.065* | |
C3 | 0.93064 (14) | 0.6769 (4) | −0.05025 (8) | 0.0626 (5) | |
H3A | 0.9458 | 0.8114 | −0.0215 | 0.075* | |
C4 | 0.85988 (12) | 0.5224 (4) | −0.04340 (8) | 0.0641 (5) | |
H4A | 0.8282 | 0.5502 | −0.0094 | 0.077* | |
C5 | 0.83609 (11) | 0.3274 (4) | −0.08673 (8) | 0.0595 (4) | |
H5A | 0.7883 | 0.2240 | −0.0815 | 0.071* | |
C6 | 0.88219 (10) | 0.2802 (3) | −0.13878 (7) | 0.0477 (3) | |
C7 | 0.85093 (11) | 0.0798 (3) | −0.18596 (9) | 0.0544 (4) | |
H7A | 0.8229 | −0.0541 | −0.1694 | 0.065* | |
C8 | 0.85761 (11) | 0.0651 (3) | −0.25014 (9) | 0.0533 (4) | |
H8A | 0.8347 | −0.0788 | −0.2727 | 0.064* | |
C9 | 0.89671 (10) | 0.2486 (3) | −0.28882 (7) | 0.0465 (3) | |
C10 | 0.86112 (11) | 0.2709 (3) | −0.35739 (8) | 0.0559 (4) | |
H10A | 0.8162 | 0.1608 | −0.3777 | 0.067* | |
C11 | 0.89126 (12) | 0.4521 (4) | −0.39514 (8) | 0.0610 (4) | |
H11A | 0.8669 | 0.4630 | −0.4406 | 0.073* | |
C12 | 0.95721 (14) | 0.6172 (4) | −0.36603 (9) | 0.0626 (4) | |
H12A | 0.9761 | 0.7428 | −0.3915 | 0.075* | |
C13 | 0.99580 (12) | 0.5967 (3) | −0.29858 (8) | 0.0550 (4) | |
H13A | 1.0412 | 0.7067 | −0.2789 | 0.066* | |
C14 | 0.96626 (9) | 0.4112 (3) | −0.26084 (7) | 0.0441 (3) | |
C15 | 1.08751 (9) | 0.2478 (3) | −0.17424 (7) | 0.0449 (3) | |
O2 | 1.23698 (9) | −0.0982 (3) | −0.06931 (6) | 0.0671 (4) | |
H2D | 1.179 (2) | 0.035 (5) | −0.0965 (13) | 0.098 (8)* | |
O3 | 1.28638 (13) | −0.1342 (4) | −0.16454 (7) | 0.0975 (6) | |
C16 | 1.28630 (12) | −0.1862 (4) | −0.10722 (9) | 0.0605 (4) | |
C17A | 1.35519 (16) | −0.3780 (5) | −0.07339 (12) | 0.0776 (6) | 0.505 (9) |
F1A | 1.3430 (5) | −0.4494 (14) | −0.0135 (3) | 0.118 (2) | 0.505 (9) |
F2A | 1.3469 (6) | −0.5914 (9) | −0.1084 (3) | 0.141 (3) | 0.505 (9) |
F3A | 1.4339 (3) | −0.3150 (14) | −0.0614 (6) | 0.152 (4) | 0.505 (9) |
C17B | 1.35519 (16) | −0.3780 (5) | −0.07339 (12) | 0.0776 (6) | 0.495 (9) |
F1B | 1.3224 (6) | −0.5483 (14) | −0.0464 (6) | 0.160 (5) | 0.495 (9) |
F2B | 1.4066 (4) | −0.4498 (14) | −0.11635 (19) | 0.112 (3) | 0.495 (9) |
F3B | 1.4203 (4) | −0.2479 (14) | −0.0311 (2) | 0.136 (3) | 0.495 (9) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0373 (6) | 0.0557 (7) | 0.0402 (6) | −0.0012 (5) | 0.0068 (4) | 0.0028 (5) |
N2 | 0.0486 (7) | 0.0859 (10) | 0.0458 (7) | 0.0122 (7) | 0.0141 (6) | 0.0052 (7) |
O1 | 0.0484 (6) | 0.0776 (8) | 0.0420 (5) | 0.0165 (5) | 0.0083 (4) | 0.0035 (5) |
C1 | 0.0400 (7) | 0.0505 (7) | 0.0403 (7) | 0.0070 (5) | 0.0063 (5) | 0.0077 (6) |
C2 | 0.0574 (9) | 0.0565 (8) | 0.0457 (8) | 0.0018 (7) | 0.0043 (6) | 0.0040 (6) |
C3 | 0.0728 (11) | 0.0676 (10) | 0.0448 (8) | 0.0186 (9) | 0.0054 (7) | −0.0014 (7) |
C4 | 0.0544 (9) | 0.0928 (13) | 0.0461 (8) | 0.0238 (9) | 0.0127 (7) | 0.0066 (8) |
C5 | 0.0423 (8) | 0.0840 (12) | 0.0539 (9) | 0.0081 (7) | 0.0137 (6) | 0.0154 (8) |
C6 | 0.0392 (7) | 0.0551 (8) | 0.0488 (8) | 0.0063 (6) | 0.0087 (6) | 0.0109 (6) |
C7 | 0.0464 (8) | 0.0545 (8) | 0.0624 (9) | −0.0065 (6) | 0.0114 (7) | 0.0101 (7) |
C8 | 0.0476 (8) | 0.0488 (8) | 0.0616 (9) | −0.0067 (6) | 0.0064 (7) | −0.0008 (7) |
C9 | 0.0409 (7) | 0.0494 (7) | 0.0481 (8) | 0.0023 (6) | 0.0065 (5) | −0.0009 (6) |
C10 | 0.0459 (8) | 0.0685 (10) | 0.0505 (8) | −0.0022 (7) | 0.0027 (6) | −0.0059 (7) |
C11 | 0.0580 (9) | 0.0786 (11) | 0.0441 (8) | 0.0077 (8) | 0.0048 (7) | 0.0052 (7) |
C12 | 0.0711 (11) | 0.0667 (10) | 0.0512 (9) | −0.0015 (8) | 0.0155 (8) | 0.0130 (7) |
C13 | 0.0564 (9) | 0.0580 (9) | 0.0509 (8) | −0.0092 (7) | 0.0114 (7) | 0.0037 (7) |
C14 | 0.0408 (7) | 0.0504 (7) | 0.0407 (7) | 0.0014 (5) | 0.0073 (5) | 0.0026 (5) |
C15 | 0.0386 (7) | 0.0540 (8) | 0.0420 (7) | −0.0033 (6) | 0.0077 (5) | 0.0003 (6) |
O2 | 0.0637 (7) | 0.0861 (9) | 0.0551 (7) | 0.0268 (7) | 0.0202 (6) | 0.0084 (6) |
O3 | 0.0980 (12) | 0.1415 (15) | 0.0589 (8) | 0.0577 (11) | 0.0295 (8) | 0.0087 (9) |
C16 | 0.0546 (9) | 0.0746 (11) | 0.0536 (9) | 0.0118 (8) | 0.0142 (7) | −0.0039 (8) |
C17A | 0.0693 (12) | 0.0863 (15) | 0.0803 (14) | 0.0246 (11) | 0.0225 (11) | 0.0025 (11) |
F1A | 0.122 (5) | 0.134 (5) | 0.104 (3) | 0.070 (4) | 0.037 (3) | 0.049 (3) |
F2A | 0.160 (6) | 0.082 (3) | 0.175 (5) | 0.039 (3) | 0.018 (4) | −0.033 (3) |
F3A | 0.0488 (17) | 0.137 (5) | 0.267 (10) | 0.008 (2) | 0.026 (4) | 0.089 (6) |
C17B | 0.0693 (12) | 0.0863 (15) | 0.0803 (14) | 0.0246 (11) | 0.0225 (11) | 0.0025 (11) |
F1B | 0.118 (4) | 0.102 (5) | 0.276 (13) | 0.035 (4) | 0.080 (7) | 0.099 (7) |
F2B | 0.107 (4) | 0.138 (5) | 0.094 (2) | 0.074 (4) | 0.031 (2) | −0.001 (2) |
F3B | 0.097 (4) | 0.216 (6) | 0.081 (2) | 0.072 (4) | −0.021 (2) | −0.028 (3) |
Geometric parameters (Å, º) top
N1—C15 | 1.3516 (19) | C7—H7A | 0.9300 |
N1—C14 | 1.4378 (18) | C8—C9 | 1.458 (2) |
N1—C1 | 1.4401 (18) | C8—H8A | 0.9300 |
N2—C15 | 1.327 (2) | C9—C14 | 1.393 (2) |
N2—H2B | 0.88 (2) | C9—C10 | 1.402 (2) |
N2—H2C | 0.89 (2) | C10—C11 | 1.374 (3) |
O1—C15 | 1.2643 (18) | C10—H10A | 0.9300 |
O1—H2D | 1.27 (3) | C11—C12 | 1.372 (3) |
C1—C2 | 1.378 (2) | C11—H11A | 0.9300 |
C1—C6 | 1.393 (2) | C12—C13 | 1.389 (2) |
C2—C3 | 1.386 (2) | C12—H12A | 0.9300 |
C2—H2A | 0.9300 | C13—C14 | 1.386 (2) |
C3—C4 | 1.376 (3) | C13—H13A | 0.9300 |
C3—H3A | 0.9300 | O2—C16 | 1.265 (2) |
C4—C5 | 1.372 (3) | O2—H2D | 1.17 (3) |
C4—H4A | 0.9300 | O3—C16 | 1.205 (2) |
C5—C6 | 1.403 (2) | C16—C17A | 1.524 (3) |
C5—H5A | 0.9300 | C17A—F3A | 1.205 (5) |
C6—C7 | 1.459 (2) | C17A—F1A | 1.331 (6) |
C7—C8 | 1.338 (2) | C17A—F2A | 1.344 (5) |
| | | |
C15—N1—C14 | 121.49 (12) | C14—C9—C10 | 117.47 (14) |
C15—N1—C1 | 119.54 (11) | C14—C9—C8 | 123.41 (14) |
C14—N1—C1 | 116.98 (11) | C10—C9—C8 | 119.09 (14) |
C15—N2—H2B | 117.4 (13) | C11—C10—C9 | 121.34 (16) |
C15—N2—H2C | 119.3 (15) | C11—C10—H10A | 119.3 |
H2B—N2—H2C | 123 (2) | C9—C10—H10A | 119.3 |
C15—O1—H2D | 120.3 (12) | C12—C11—C10 | 120.25 (15) |
C2—C1—C6 | 121.67 (14) | C12—C11—H11A | 119.9 |
C2—C1—N1 | 119.48 (14) | C10—C11—H11A | 119.9 |
C6—C1—N1 | 118.84 (13) | C11—C12—C13 | 120.03 (16) |
C1—C2—C3 | 119.67 (17) | C11—C12—H12A | 120.0 |
C1—C2—H2A | 120.2 | C13—C12—H12A | 120.0 |
C3—C2—H2A | 120.2 | C14—C13—C12 | 119.58 (16) |
C4—C3—C2 | 119.95 (17) | C14—C13—H13A | 120.2 |
C4—C3—H3A | 120.0 | C12—C13—H13A | 120.2 |
C2—C3—H3A | 120.0 | C13—C14—C9 | 121.25 (14) |
C5—C4—C3 | 120.06 (16) | C13—C14—N1 | 119.89 (13) |
C5—C4—H4A | 120.0 | C9—C14—N1 | 118.84 (13) |
C3—C4—H4A | 120.0 | O1—C15—N2 | 122.09 (14) |
C4—C5—C6 | 121.57 (17) | O1—C15—N1 | 118.60 (13) |
C4—C5—H5A | 119.2 | N2—C15—N1 | 119.31 (13) |
C6—C5—H5A | 119.2 | C16—O2—H2D | 113.8 (13) |
C1—C6—C5 | 116.98 (16) | O3—C16—O2 | 128.58 (18) |
C1—C6—C7 | 123.47 (14) | O3—C16—C17A | 117.77 (17) |
C5—C6—C7 | 119.53 (15) | O2—C16—C17A | 113.64 (16) |
C8—C7—C6 | 127.95 (15) | F3A—C17A—F1A | 101.7 (6) |
C8—C7—H7A | 116.0 | F3A—C17A—F2A | 109.3 (5) |
C6—C7—H7A | 116.0 | F1A—C17A—F2A | 103.3 (4) |
C7—C8—C9 | 127.52 (15) | F3A—C17A—C16 | 116.7 (3) |
C7—C8—H8A | 116.2 | F1A—C17A—C16 | 114.0 (3) |
C9—C8—H8A | 116.2 | F2A—C17A—C16 | 110.7 (3) |
| | | |
C15—N1—C1—C2 | 81.92 (18) | C10—C11—C12—C13 | 2.0 (3) |
C14—N1—C1—C2 | −113.89 (15) | C11—C12—C13—C14 | −1.0 (3) |
C15—N1—C1—C6 | −96.79 (16) | C12—C13—C14—C9 | −1.8 (3) |
C14—N1—C1—C6 | 67.40 (17) | C12—C13—C14—N1 | 176.28 (15) |
C6—C1—C2—C3 | 2.0 (2) | C10—C9—C14—C13 | 3.4 (2) |
N1—C1—C2—C3 | −176.65 (13) | C8—C9—C14—C13 | −174.33 (15) |
C1—C2—C3—C4 | 0.7 (2) | C10—C9—C14—N1 | −174.70 (13) |
C2—C3—C4—C5 | −1.5 (3) | C8—C9—C14—N1 | 7.6 (2) |
C3—C4—C5—C6 | −0.2 (3) | C15—N1—C14—C13 | −82.98 (19) |
C2—C1—C6—C5 | −3.6 (2) | C1—N1—C14—C13 | 113.15 (16) |
N1—C1—C6—C5 | 175.03 (13) | C15—N1—C14—C9 | 95.12 (17) |
C2—C1—C6—C7 | 175.40 (14) | C1—N1—C14—C9 | −68.75 (18) |
N1—C1—C6—C7 | −5.9 (2) | C14—N1—C15—O1 | −167.38 (14) |
C4—C5—C6—C1 | 2.7 (2) | C1—N1—C15—O1 | −3.9 (2) |
C4—C5—C6—C7 | −176.33 (15) | C14—N1—C15—N2 | 12.1 (2) |
C1—C6—C7—C8 | −28.7 (3) | C1—N1—C15—N2 | 175.53 (14) |
C5—C6—C7—C8 | 150.31 (18) | O3—C16—C17A—F3A | 70.1 (8) |
C6—C7—C8—C9 | −1.0 (3) | O2—C16—C17A—F3A | −108.5 (7) |
C7—C8—C9—C14 | 29.1 (3) | O3—C16—C17A—F1A | −171.6 (5) |
C7—C8—C9—C10 | −148.54 (18) | O2—C16—C17A—F1A | 9.8 (5) |
C14—C9—C10—C11 | −2.4 (2) | O3—C16—C17A—F2A | −55.7 (6) |
C8—C9—C10—C11 | 175.46 (16) | O2—C16—C17A—F2A | 125.7 (5) |
C9—C10—C11—C12 | −0.3 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···O3 | 0.88 (2) | 2.03 (2) | 2.904 (2) | 169.1 (19) |
N2—H2C···O3i | 0.89 (2) | 2.36 (2) | 3.003 (2) | 129.2 (19) |
O2—H2D···O1 | 1.17 (3) | 1.27 (3) | 2.4349 (16) | 168 (2) |
O1—H2D···O3 | 1.27 (3) | 2.50 (3) | 3.4435 (18) | 128.9 (17) |
Symmetry code: (i) −x+5/2, y+1/2, −z−1/2. |