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Hydrogen bonding between urea functionalities is a common structural motif employed in crystal-engineering studies. Crystallization of 1,3-bis(3-fluorophenyl)urea, C13H10F2N2O, from many solvents yielded concomitant mixtures of at least two polymorphs. In the monoclinic form, one-dimensional chains of hydrogen-bonded urea molecules align in an antiparallel orientation, as is typical of many diphenylureas. In the orthorhombic form, one-dimensional chains of hydrogen-bonded urea molecules have a parallel orientation rarely observed in symmetrically substituted diphenylureas.
Supporting information
CCDC references: 1500641; 1500640
Data collection: CrysAlis CCD (Oxford Diffraction, 2005) for (I); APEX2 (Bruker, 2014) for (II). Cell refinement: CrysAlis RED (Oxford Diffraction, 2005) for (I); APEX2 (Bruker, 2014) for (II). Data reduction: CrysAlis RED (Oxford Diffraction, 2005) for (I); SAINT (Bruker, 2014) for (II). Program(s) used to solve structure: SHELXTL (Sheldrick, 2008) for (I); SHELXT (Sheldrick, 2015a) for (II). For both compounds, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: SHELXTL (Bruker, 2014); software used to prepare material for publication: XCIF (Bruker, 2014) and publCIF (Westrip, 2010).
(I) 1,3-Bis(3-fluorophenyl)urea
top
Crystal data top
C13H10F2N2O | F(000) = 1024 |
Mr = 248.23 | Dx = 1.463 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 20.6614 (19) Å | Cell parameters from 2884 reflections |
b = 12.6052 (11) Å | θ = 1.9–28.6° |
c = 9.1691 (9) Å | µ = 0.12 mm−1 |
β = 109.284 (9)° | T = 110 K |
V = 2254.0 (4) Å3 | Prism, colorless |
Z = 8 | 0.23 × 0.09 × 0.03 mm |
Data collection top
Multiwire proportional diffractometer | 2858 independent reflections |
Radiation source: sealed tube | 2048 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
phi and ω scans | θmax = 28.6°, θmin = 3.9° |
Absorption correction: numerical (CrysAlis RED; Oxford Diffraction, 2005) | h = −27→27 |
Tmin = 0.957, Tmax = 0.993 | k = −16→16 |
12889 measured reflections | l = −12→12 |
Refinement top
Refinement on F2 | 2 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.145 | w = 1/[σ2(Fo2) + (0.0722P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.13 | (Δ/σ)max < 0.001 |
2858 reflections | Δρmax = 0.28 e Å−3 |
179 parameters | Δρmin = −0.24 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. |
Refinement. Structure was phased by direct methods (Sheldrick, 2015). Systematic
conditions suggested the unambiguous space group. The space group choice
was confirmed by successful convergence of the full-matrix least-squares
refinement on F2. The final map had no significant features. A final
analysis of variance between observed and calculated structure factors
showed some dependence on amplitude and little dependence on resolution. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.12765 (6) | 0.02147 (9) | 0.59284 (12) | 0.0251 (3) | |
N1 | 0.10058 (7) | −0.07341 (11) | 0.77665 (17) | 0.0246 (4) | |
H1 | 0.1032 (10) | −0.0784 (16) | 0.8748 (18) | 0.037* | |
N2 | 0.14840 (7) | 0.09098 (11) | 0.83494 (16) | 0.0240 (3) | |
H2 | 0.1430 (10) | 0.0760 (16) | 0.9273 (19) | 0.036* | |
F1 | 0.07380 (7) | −0.44765 (9) | 0.73146 (14) | 0.0499 (4) | |
F2 | 0.24104 (8) | 0.35311 (11) | 0.57553 (16) | 0.0404 (5) | 0.806 (4) |
F2' | 0.1802 (3) | 0.4426 (5) | 0.9954 (7) | 0.045 (2) | 0.194 (4) |
C1 | 0.12571 (8) | 0.01375 (13) | 0.72571 (18) | 0.0206 (4) | |
C2 | 0.07261 (9) | −0.16392 (13) | 0.6848 (2) | 0.0235 (4) | |
C3 | 0.08879 (9) | −0.26293 (14) | 0.7515 (2) | 0.0279 (4) | |
H3 | 0.1196 | −0.2706 | 0.8540 | 0.033* | |
C4 | 0.05883 (10) | −0.35044 (14) | 0.6648 (2) | 0.0317 (4) | |
C5 | 0.01393 (10) | −0.34403 (15) | 0.5156 (2) | 0.0335 (5) | |
H5 | −0.0058 | −0.4059 | 0.4591 | 0.040* | |
C6 | −0.00125 (9) | −0.24426 (14) | 0.4516 (2) | 0.0294 (4) | |
H6 | −0.0318 | −0.2372 | 0.3488 | 0.035* | |
C7 | 0.02722 (9) | −0.15437 (14) | 0.5345 (2) | 0.0264 (4) | |
H7 | 0.0158 | −0.0862 | 0.4890 | 0.032* | |
C8 | 0.17014 (8) | 0.19427 (13) | 0.81364 (18) | 0.0223 (4) | |
C9 | 0.19741 (9) | 0.22055 (15) | 0.6986 (2) | 0.0269 (4) | |
H9 | 0.2027 | 0.1686 | 0.6283 | 0.032* | |
C10 | 0.21657 (9) | 0.32459 (16) | 0.6900 (2) | 0.0308 (4) | |
H10 | 0.2352 | 0.3428 | 0.6115 | 0.037* | 0.194 (4) |
C11 | 0.21032 (9) | 0.40341 (15) | 0.7879 (2) | 0.0311 (4) | |
H11 | 0.2235 | 0.4744 | 0.7773 | 0.037* | |
C12 | 0.18407 (9) | 0.37474 (15) | 0.9026 (2) | 0.0289 (4) | |
H12 | 0.1795 | 0.4270 | 0.9732 | 0.035* | 0.806 (4) |
C13 | 0.16428 (8) | 0.27157 (14) | 0.91671 (19) | 0.0239 (4) | |
H13A | 0.1466 | 0.2535 | 0.9969 | 0.029* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0324 (7) | 0.0267 (7) | 0.0168 (6) | 0.0021 (5) | 0.0089 (5) | −0.0002 (5) |
N1 | 0.0333 (8) | 0.0238 (8) | 0.0177 (7) | −0.0039 (6) | 0.0097 (6) | −0.0033 (6) |
N2 | 0.0315 (8) | 0.0248 (8) | 0.0157 (7) | −0.0046 (6) | 0.0077 (6) | −0.0015 (6) |
F1 | 0.0621 (9) | 0.0234 (6) | 0.0516 (8) | 0.0004 (6) | 0.0017 (6) | 0.0049 (5) |
F2 | 0.0503 (9) | 0.0424 (9) | 0.0381 (9) | −0.0132 (7) | 0.0274 (7) | 0.0032 (6) |
F2' | 0.051 (4) | 0.037 (4) | 0.047 (4) | −0.004 (3) | 0.015 (3) | −0.014 (3) |
C1 | 0.0207 (8) | 0.0242 (9) | 0.0160 (8) | 0.0032 (7) | 0.0046 (6) | 0.0000 (6) |
C2 | 0.0245 (9) | 0.0243 (9) | 0.0229 (9) | 0.0001 (7) | 0.0096 (7) | −0.0030 (7) |
C3 | 0.0284 (9) | 0.0283 (10) | 0.0251 (9) | −0.0017 (8) | 0.0065 (7) | −0.0007 (7) |
C4 | 0.0361 (11) | 0.0211 (9) | 0.0364 (11) | 0.0015 (8) | 0.0100 (8) | 0.0022 (8) |
C5 | 0.0361 (11) | 0.0259 (10) | 0.0348 (11) | −0.0035 (8) | 0.0067 (9) | −0.0086 (8) |
C6 | 0.0269 (9) | 0.0320 (10) | 0.0261 (9) | 0.0012 (8) | 0.0043 (7) | −0.0034 (8) |
C7 | 0.0273 (9) | 0.0263 (9) | 0.0245 (9) | 0.0036 (7) | 0.0072 (7) | −0.0014 (7) |
C8 | 0.0200 (8) | 0.0230 (9) | 0.0204 (8) | −0.0022 (7) | 0.0020 (7) | 0.0013 (7) |
C9 | 0.0267 (9) | 0.0321 (10) | 0.0220 (9) | −0.0023 (8) | 0.0083 (7) | −0.0011 (7) |
C10 | 0.0281 (10) | 0.0387 (11) | 0.0263 (9) | −0.0073 (8) | 0.0099 (7) | 0.0056 (8) |
C11 | 0.0295 (10) | 0.0269 (10) | 0.0334 (10) | −0.0048 (8) | 0.0054 (8) | 0.0042 (8) |
C12 | 0.0284 (10) | 0.0271 (9) | 0.0272 (10) | −0.0009 (8) | 0.0035 (8) | −0.0021 (8) |
C13 | 0.0227 (8) | 0.0288 (9) | 0.0191 (8) | −0.0017 (7) | 0.0055 (7) | 0.0004 (7) |
Geometric parameters (Å, º) top
O1—C1 | 1.2360 (18) | C5—H5 | 0.9500 |
N1—C1 | 1.362 (2) | C6—C7 | 1.383 (2) |
N1—C2 | 1.423 (2) | C6—H6 | 0.9500 |
N1—H1 | 0.886 (15) | C7—H7 | 0.9500 |
N2—C1 | 1.364 (2) | C8—C9 | 1.390 (2) |
N2—C8 | 1.412 (2) | C8—C13 | 1.390 (2) |
N2—H2 | 0.909 (15) | C9—C10 | 1.380 (3) |
F1—C4 | 1.359 (2) | C9—H9 | 0.9500 |
F2—C10 | 1.355 (2) | C10—C11 | 1.374 (3) |
F2'—C12 | 1.227 (6) | C10—H10 | 0.9500 |
C2—C3 | 1.382 (2) | C11—C12 | 1.381 (3) |
C2—C7 | 1.392 (2) | C11—H11 | 0.9500 |
C3—C4 | 1.381 (3) | C12—C13 | 1.382 (2) |
C3—H3 | 0.9500 | C12—H12 | 0.9500 |
C4—C5 | 1.379 (3) | C13—H13A | 0.9500 |
C5—C6 | 1.379 (3) | | |
| | | |
C1—N1—C2 | 124.76 (14) | C6—C7—H7 | 120.1 |
C1—N1—H1 | 120.2 (13) | C2—C7—H7 | 120.1 |
C2—N1—H1 | 114.9 (13) | C9—C8—C13 | 119.79 (16) |
C1—N2—C8 | 127.19 (14) | C9—C8—N2 | 123.51 (16) |
C1—N2—H2 | 114.7 (13) | C13—C8—N2 | 116.69 (15) |
C8—N2—H2 | 117.6 (13) | C10—C9—C8 | 117.79 (17) |
O1—C1—N1 | 122.80 (15) | C10—C9—H9 | 121.1 |
O1—C1—N2 | 123.54 (15) | C8—C9—H9 | 121.1 |
N1—C1—N2 | 113.66 (14) | F2—C10—C11 | 117.00 (17) |
C3—C2—C7 | 120.11 (16) | F2—C10—C9 | 118.97 (18) |
C3—C2—N1 | 118.08 (16) | C11—C10—C9 | 123.99 (17) |
C7—C2—N1 | 121.72 (16) | C11—C10—H10 | 118.0 |
C4—C3—C2 | 118.01 (17) | C9—C10—H10 | 118.0 |
C4—C3—H3 | 121.0 | C10—C11—C12 | 117.00 (17) |
C2—C3—H3 | 121.0 | C10—C11—H11 | 121.5 |
F1—C4—C5 | 118.55 (16) | C12—C11—H11 | 121.5 |
F1—C4—C3 | 117.99 (17) | F2'—C12—C11 | 118.5 (3) |
C5—C4—C3 | 123.46 (17) | F2'—C12—C13 | 120.1 (3) |
C4—C5—C6 | 117.35 (17) | C11—C12—C13 | 121.35 (17) |
C4—C5—H5 | 121.3 | C11—C12—H12 | 119.3 |
C6—C5—H5 | 121.3 | C13—C12—H12 | 119.3 |
C5—C6—C7 | 121.17 (17) | C12—C13—C8 | 120.07 (16) |
C5—C6—H6 | 119.4 | C12—C13—H13A | 120.0 |
C7—C6—H6 | 119.4 | C8—C13—H13A | 120.0 |
C6—C7—C2 | 119.89 (17) | | |
| | | |
C2—N1—C1—O1 | −1.3 (3) | N1—C2—C7—C6 | −177.02 (16) |
C2—N1—C1—N2 | 178.71 (15) | C1—N2—C8—C9 | −26.6 (3) |
C8—N2—C1—O1 | 7.5 (3) | C1—N2—C8—C13 | 154.41 (16) |
C8—N2—C1—N1 | −172.58 (16) | C13—C8—C9—C10 | −1.2 (2) |
C1—N1—C2—C3 | 139.16 (17) | N2—C8—C9—C10 | 179.85 (16) |
C1—N1—C2—C7 | −44.3 (2) | C8—C9—C10—F2 | −177.69 (15) |
C7—C2—C3—C4 | 0.1 (3) | C8—C9—C10—C11 | 0.0 (3) |
N1—C2—C3—C4 | 176.76 (16) | F2—C10—C11—C12 | 178.72 (16) |
C2—C3—C4—F1 | −178.85 (16) | C9—C10—C11—C12 | 1.0 (3) |
C2—C3—C4—C5 | 0.1 (3) | C10—C11—C12—F2' | 177.4 (4) |
F1—C4—C5—C6 | 178.96 (17) | C10—C11—C12—C13 | −0.7 (3) |
C3—C4—C5—C6 | 0.0 (3) | F2'—C12—C13—C8 | −178.5 (4) |
C4—C5—C6—C7 | −0.4 (3) | C11—C12—C13—C8 | −0.4 (3) |
C5—C6—C7—C2 | 0.7 (3) | C9—C8—C13—C12 | 1.5 (2) |
C3—C2—C7—C6 | −0.5 (3) | N2—C8—C13—C12 | −179.55 (15) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1i | 0.91 (2) | 2.06 (2) | 2.9076 (18) | 155 (2) |
N1—H1···O1i | 0.89 (2) | 2.02 (2) | 2.8417 (18) | 153 (2) |
Symmetry code: (i) x, −y, z+1/2. |
(II) 1,3-Bis(3-fluorophenyl)urea
top
Crystal data top
C13H10F2N2O | Dx = 1.492 Mg m−3 |
Mr = 248.23 | Melting point = 143.8–147.6 K |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
a = 23.5797 (19) Å | Cell parameters from 4113 reflections |
b = 10.1792 (8) Å | θ = 2.6–27.4° |
c = 4.6031 (4) Å | µ = 0.12 mm−1 |
V = 1104.85 (16) Å3 | T = 100 K |
Z = 4 | Needle, colorless |
F(000) = 512 | 0.60 × 0.10 × 0.06 mm |
Data collection top
Bruker APEXII SMART platform CCD diffractometer | 2624 independent reflections |
Radiation source: fine-focus sealed tube | 2443 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ω scans | θmax = 28.2°, θmin = 1.7° |
Absorption correction: multi-scan SADABS V2014/4 (Bruker, 2014) | h = −31→31 |
Tmin = 0.932, Tmax = 0.993 | k = −12→13 |
9603 measured reflections | l = −6→6 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.030 | w = 1/[σ2(Fo2) + (0.034P)2 + 0.2739P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.072 | (Δ/σ)max < 0.001 |
S = 1.05 | Δρmax = 0.22 e Å−3 |
2624 reflections | Δρmin = −0.17 e Å−3 |
179 parameters | Absolute structure: Flack x determined using 989 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
3 restraints | Absolute structure parameter: −0.4 (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. |
Refinement. Structure was phased by direct methods (Sheldrick, 2015). Systematic
conditions suggested the unambiguous space group. The space group
choice was confirmed by successful convergence of the full-matrix
least-squares refinement on F2. The final map had no significant
features. A final analysis of variance between observed and calculated
structure factors showed little dependence on amplitude and resolution. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.37757 (6) | 1.07011 (12) | 0.6264 (3) | 0.0167 (3) | |
N1 | 0.35674 (7) | 1.17231 (15) | 1.0544 (4) | 0.0155 (3) | |
H1 | 0.3632 (10) | 1.168 (2) | 1.239 (5) | 0.023* | |
N2 | 0.40708 (7) | 0.98087 (15) | 1.0560 (4) | 0.0151 (3) | |
H2 | 0.4080 (10) | 0.995 (2) | 1.238 (5) | 0.023* | |
F1 | 0.22284 (5) | 1.37274 (13) | 0.4117 (3) | 0.0311 (3) | |
F2 | 0.41590 (5) | 0.60920 (12) | 0.4201 (3) | 0.0238 (4) | 0.932 (4) |
F2' | 0.5579 (8) | 0.6757 (17) | 1.074 (5) | 0.033 (6) | 0.068 (4) |
C1 | 0.37987 (7) | 1.07346 (17) | 0.8938 (4) | 0.0133 (3) | |
C2 | 0.33047 (7) | 1.28461 (17) | 0.9336 (4) | 0.0143 (3) | |
C3 | 0.28907 (8) | 1.27192 (19) | 0.7186 (4) | 0.0173 (4) | |
H3 | 0.2790 | 1.1883 | 0.6430 | 0.021* | |
C4 | 0.26326 (8) | 1.38512 (19) | 0.6199 (4) | 0.0200 (4) | |
C5 | 0.27633 (9) | 1.5085 (2) | 0.7213 (5) | 0.0223 (4) | |
H5 | 0.2578 | 1.5842 | 0.6469 | 0.027* | |
C6 | 0.31752 (8) | 1.51897 (18) | 0.9358 (5) | 0.0206 (4) | |
H6 | 0.3271 | 1.6029 | 1.0113 | 0.025* | |
C7 | 0.34474 (8) | 1.40791 (18) | 1.0408 (5) | 0.0175 (4) | |
H7 | 0.3731 | 1.4161 | 1.1861 | 0.021* | |
C8 | 0.43509 (7) | 0.86969 (17) | 0.9403 (4) | 0.0143 (4) | |
C9 | 0.41038 (8) | 0.79368 (17) | 0.7222 (4) | 0.0159 (4) | |
H9 | 0.3748 | 0.8166 | 0.6399 | 0.019* | |
C10 | 0.43970 (8) | 0.68379 (18) | 0.6308 (4) | 0.0182 (4) | |
H10A | 0.4233 | 0.6316 | 0.4817 | 0.022* | 0.068 (4) |
C11 | 0.49123 (8) | 0.64515 (18) | 0.7422 (5) | 0.0190 (4) | |
H11 | 0.5099 | 0.5687 | 0.6729 | 0.023* | |
C12 | 0.51479 (8) | 0.72211 (18) | 0.9597 (4) | 0.0194 (4) | |
H12 | 0.5501 | 0.6976 | 1.0426 | 0.023* | 0.932 (4) |
C13 | 0.48738 (8) | 0.83459 (18) | 1.0582 (4) | 0.0164 (4) | |
H13 | 0.5042 | 0.8873 | 1.2051 | 0.020* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0219 (7) | 0.0183 (6) | 0.0099 (7) | 0.0035 (5) | 0.0000 (5) | −0.0003 (5) |
N1 | 0.0220 (8) | 0.0153 (7) | 0.0091 (7) | 0.0034 (6) | −0.0019 (6) | 0.0004 (6) |
N2 | 0.0215 (8) | 0.0149 (7) | 0.0090 (7) | 0.0035 (6) | −0.0011 (6) | −0.0024 (6) |
F1 | 0.0274 (6) | 0.0424 (7) | 0.0236 (7) | 0.0102 (5) | −0.0115 (6) | −0.0018 (6) |
F2 | 0.0286 (7) | 0.0203 (6) | 0.0225 (7) | −0.0011 (5) | −0.0044 (6) | −0.0096 (6) |
F2' | 0.033 (11) | 0.024 (10) | 0.041 (12) | 0.005 (8) | −0.001 (10) | 0.001 (9) |
C1 | 0.0131 (8) | 0.0145 (8) | 0.0125 (9) | −0.0023 (6) | 0.0004 (7) | 0.0000 (7) |
C2 | 0.0147 (8) | 0.0167 (8) | 0.0116 (8) | 0.0024 (6) | 0.0026 (7) | 0.0011 (7) |
C3 | 0.0179 (9) | 0.0203 (9) | 0.0139 (9) | 0.0005 (7) | 0.0002 (7) | −0.0024 (7) |
C4 | 0.0162 (9) | 0.0303 (10) | 0.0135 (9) | 0.0049 (8) | −0.0018 (7) | 0.0005 (8) |
C5 | 0.0253 (10) | 0.0225 (10) | 0.0190 (10) | 0.0104 (8) | 0.0030 (8) | 0.0053 (8) |
C6 | 0.0245 (9) | 0.0153 (8) | 0.0220 (10) | 0.0012 (7) | 0.0039 (8) | −0.0009 (8) |
C7 | 0.0169 (8) | 0.0198 (9) | 0.0158 (9) | 0.0014 (7) | −0.0006 (8) | −0.0014 (7) |
C8 | 0.0177 (8) | 0.0133 (8) | 0.0119 (8) | 0.0001 (6) | 0.0032 (7) | 0.0019 (7) |
C9 | 0.0174 (8) | 0.0168 (8) | 0.0133 (9) | −0.0007 (7) | −0.0010 (7) | 0.0007 (7) |
C10 | 0.0252 (10) | 0.0151 (8) | 0.0143 (9) | −0.0041 (7) | 0.0013 (8) | −0.0025 (7) |
C11 | 0.0240 (9) | 0.0145 (8) | 0.0185 (9) | 0.0033 (7) | 0.0045 (8) | −0.0006 (7) |
C12 | 0.0186 (9) | 0.0200 (9) | 0.0197 (10) | 0.0032 (7) | 0.0011 (8) | 0.0016 (8) |
C13 | 0.0186 (9) | 0.0169 (9) | 0.0136 (9) | −0.0010 (7) | −0.0014 (7) | −0.0006 (7) |
Geometric parameters (Å, º) top
O1—C1 | 1.232 (2) | C5—H5 | 0.9500 |
N1—C1 | 1.362 (2) | C6—C7 | 1.387 (3) |
N1—C2 | 1.414 (2) | C6—H6 | 0.9500 |
N1—H1 | 0.86 (2) | C7—H7 | 0.9500 |
N2—C1 | 1.363 (2) | C8—C13 | 1.394 (3) |
N2—C8 | 1.415 (2) | C8—C9 | 1.395 (3) |
N2—H2 | 0.85 (2) | C9—C10 | 1.381 (3) |
F1—C4 | 1.358 (2) | C9—H9 | 0.9500 |
F2—C10 | 1.354 (2) | C10—C11 | 1.376 (3) |
F2'—C12 | 1.238 (19) | C10—H10A | 0.9500 |
C2—C7 | 1.390 (3) | C11—C12 | 1.387 (3) |
C2—C3 | 1.396 (3) | C11—H11 | 0.9500 |
C3—C4 | 1.380 (3) | C12—C13 | 1.391 (3) |
C3—H3 | 0.9500 | C12—H12 | 0.9500 |
C4—C5 | 1.375 (3) | C13—H13 | 0.9500 |
C5—C6 | 1.389 (3) | | |
| | | |
C1—N1—C2 | 123.99 (16) | C6—C7—H7 | 120.0 |
C1—N1—H1 | 115.4 (16) | C2—C7—H7 | 120.0 |
C2—N1—H1 | 120.1 (16) | C13—C8—C9 | 120.50 (16) |
C1—N2—C8 | 124.53 (16) | C13—C8—N2 | 118.14 (17) |
C1—N2—H2 | 115.5 (16) | C9—C8—N2 | 121.31 (16) |
C8—N2—H2 | 119.9 (16) | C10—C9—C8 | 117.35 (17) |
O1—C1—N1 | 122.99 (17) | C10—C9—H9 | 121.3 |
O1—C1—N2 | 123.28 (16) | C8—C9—H9 | 121.3 |
N1—C1—N2 | 113.70 (16) | F2—C10—C11 | 118.22 (17) |
C7—C2—C3 | 120.31 (18) | F2—C10—C9 | 117.73 (17) |
C7—C2—N1 | 118.95 (17) | C11—C10—C9 | 124.05 (18) |
C3—C2—N1 | 120.69 (17) | C11—C10—H10A | 118.0 |
C4—C3—C2 | 117.68 (18) | C9—C10—H10A | 118.0 |
C4—C3—H3 | 121.2 | C10—C11—C12 | 117.47 (17) |
C2—C3—H3 | 121.2 | C10—C11—H11 | 121.3 |
F1—C4—C5 | 118.79 (17) | C12—C11—H11 | 121.3 |
F1—C4—C3 | 117.68 (17) | F2'—C12—C11 | 114.9 (9) |
C5—C4—C3 | 123.53 (18) | F2'—C12—C13 | 123.8 (10) |
C4—C5—C6 | 117.89 (17) | C11—C12—C13 | 120.92 (17) |
C4—C5—H5 | 121.1 | C11—C12—H12 | 119.5 |
C6—C5—H5 | 121.1 | C13—C12—H12 | 119.5 |
C7—C6—C5 | 120.59 (18) | C12—C13—C8 | 119.70 (18) |
C7—C6—H6 | 119.7 | C12—C13—H13 | 120.2 |
C5—C6—H6 | 119.7 | C8—C13—H13 | 120.2 |
C6—C7—C2 | 120.01 (19) | | |
| | | |
C2—N1—C1—O1 | −3.6 (3) | N1—C2—C7—C6 | −176.84 (18) |
C2—N1—C1—N2 | 174.72 (16) | C1—N2—C8—C13 | 137.98 (19) |
C8—N2—C1—O1 | −0.9 (3) | C1—N2—C8—C9 | −44.5 (3) |
C8—N2—C1—N1 | −179.16 (17) | C13—C8—C9—C10 | 0.1 (3) |
C1—N1—C2—C7 | −132.70 (19) | N2—C8—C9—C10 | −177.35 (17) |
C1—N1—C2—C3 | 50.0 (3) | C8—C9—C10—F2 | 179.73 (17) |
C7—C2—C3—C4 | −0.2 (3) | C8—C9—C10—C11 | 0.3 (3) |
N1—C2—C3—C4 | 177.02 (17) | F2—C10—C11—C12 | −179.47 (17) |
C2—C3—C4—F1 | −179.75 (17) | C9—C10—C11—C12 | 0.0 (3) |
C2—C3—C4—C5 | 0.2 (3) | C10—C11—C12—F2' | 172.5 (11) |
F1—C4—C5—C6 | 179.54 (18) | C10—C11—C12—C13 | −0.6 (3) |
C3—C4—C5—C6 | −0.4 (3) | F2'—C12—C13—C8 | −171.5 (12) |
C4—C5—C6—C7 | 0.6 (3) | C11—C12—C13—C8 | 1.0 (3) |
C5—C6—C7—C2 | −0.7 (3) | C9—C8—C13—C12 | −0.7 (3) |
C3—C2—C7—C6 | 0.5 (3) | N2—C8—C13—C12 | 176.81 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 (2) | 2.07 (2) | 2.874 (2) | 154 (2) |
N2—H2···O1i | 0.85 (2) | 2.07 (2) | 2.864 (2) | 155 (2) |
Symmetry code: (i) x, y, z+1. |
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