The title compound, C
20H
14FN
3, contains one conventional N—H
N hydrogen bond which links the molecules into spiral chains running parallel to the
c axis; the conformation of this chain appears to be stabilized by an antiparallel C—H
F contact. The structure also contains non-localized solvent in isolated cavities which lie along the crystallographic threefold axis.
Supporting information
CCDC reference: 227016
Key indicators
- Single-crystal X-ray study
- T = 120 K
- R factor = 0.057
- wR factor = 0.162
- Data-to-parameter ratio = 17.3
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT601_ALERT_2_A Structure Contains Solvent Accessible VOIDS of . 257.00 A 3
| Author Response: ...The difference map also revealed several peaks lying in
voids
on and around the 3-fold axis. These could not be resolved to give a
sensible
molecules and the SQUEEZE option in PLATON, Spek, 2003, was used to
remove
the contribution of electron density from these solvent accessible
voids.
|
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.105
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).
6-(4-fluorophenyl)-5,6-dihydrobenzimidazo[1,2-
c]quinazoline
top
Crystal data top
C20H14FN3 | Melting point: 477 K |
Mr = 315.34 | Mo Kα radiation, λ = 0.71073 Å |
Trigonal, R3 | Cell parameters from 3780 reflections |
a = 22.3211 (8) Å | θ = 3.0–27.5° |
c = 17.2220 (9) Å | µ = 0.09 mm−1 |
V = 7431.0 (5) Å3 | T = 120 K |
Z = 18 | Plate, colourless |
F(000) = 2952 | 0.26 × 0.20 × 0.06 mm |
Dx = 1.268 Mg m−3 | |
Data collection top
Nonius KappaCCD diffractometer | 3780 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2552 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.105 |
φ scans and ω scans with κ offsets | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | h = −28→28 |
Tmin = 0.978, Tmax = 0.995 | k = −28→28 |
28120 measured reflections | l = −19→22 |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.162 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0894P)2 + 1.7404P] where P = (Fo2 + 2Fc2)/3 |
3780 reflections | (Δ/σ)max < 0.001 |
218 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
Special details top
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm
(Fox & Holmes, 1966) which effectively corrects for absorption effects. High
redundancy data were used in the scaling program hence the 'multi-scan' code
word was used. No transmission coefficients are available from the program
(only scale factors for each frame). The scale factors in the experimental
table are calculated from the 'size' command in the SHELXL97 input
file. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
F24 | 0.18149 (7) | −0.04499 (8) | 0.51008 (7) | 0.0563 (4) | |
N1 | 0.38847 (8) | 0.06017 (8) | 0.23125 (9) | 0.0276 (4) | |
N2A | 0.29815 (8) | 0.07012 (8) | 0.17526 (9) | 0.0243 (4) | |
N7 | 0.28403 (8) | 0.07132 (8) | 0.04651 (9) | 0.0274 (4) | |
C2 | 0.34037 (10) | 0.08491 (10) | 0.24630 (11) | 0.0263 (4) | |
C21 | 0.29767 (10) | 0.04971 (10) | 0.31700 (11) | 0.0264 (4) | |
C22 | 0.29940 (11) | 0.08895 (11) | 0.38019 (12) | 0.0356 (5) | |
C23 | 0.26068 (12) | 0.05709 (13) | 0.44604 (12) | 0.0423 (6) | |
C24 | 0.22083 (11) | −0.01334 (12) | 0.44567 (12) | 0.0372 (5) | |
C25 | 0.21763 (10) | −0.05384 (11) | 0.38510 (11) | 0.0337 (5) | |
C26 | 0.25657 (10) | −0.02187 (10) | 0.32011 (12) | 0.0292 (4) | |
C2B | 0.23286 (9) | 0.06239 (9) | 0.16472 (11) | 0.0251 (4) | |
C3 | 0.18229 (10) | 0.05797 (10) | 0.21555 (12) | 0.0303 (5) | |
C4 | 0.12350 (10) | 0.05297 (10) | 0.18223 (12) | 0.0339 (5) | |
C5 | 0.11532 (10) | 0.05256 (10) | 0.10223 (13) | 0.0351 (5) | |
C6 | 0.16498 (10) | 0.05669 (10) | 0.05210 (12) | 0.0331 (5) | |
C6A | 0.22490 (10) | 0.06211 (9) | 0.08405 (11) | 0.0272 (4) | |
C7A | 0.32670 (10) | 0.07739 (9) | 0.10287 (10) | 0.0250 (4) | |
C7B | 0.39741 (10) | 0.09219 (9) | 0.09691 (11) | 0.0254 (4) | |
C8 | 0.43463 (10) | 0.11331 (10) | 0.02767 (12) | 0.0317 (5) | |
C9 | 0.50144 (11) | 0.12489 (11) | 0.02453 (13) | 0.0372 (5) | |
C10 | 0.53137 (11) | 0.11564 (11) | 0.09091 (13) | 0.0374 (5) | |
C11 | 0.49543 (10) | 0.09520 (10) | 0.16012 (12) | 0.0323 (5) | |
C11A | 0.42795 (9) | 0.08351 (9) | 0.16397 (11) | 0.0265 (4) | |
H1 | 0.4088 | 0.0601 | 0.2782 | 0.033* | |
H2 | 0.3669 | 0.1360 | 0.2552 | 0.032* | |
H22 | 0.3272 | 0.1379 | 0.3784 | 0.043* | |
H23 | 0.2619 | 0.0834 | 0.4900 | 0.051* | |
H25 | 0.1894 | −0.1027 | 0.3875 | 0.040* | |
H26 | 0.2553 | −0.0490 | 0.2770 | 0.035* | |
H3 | 0.1878 | 0.0584 | 0.2703 | 0.036* | |
H4 | 0.0878 | 0.0497 | 0.2150 | 0.041* | |
H5 | 0.0743 | 0.0493 | 0.0817 | 0.042* | |
H6 | 0.1588 | 0.0559 | −0.0025 | 0.040* | |
H8 | 0.4140 | 0.1197 | −0.0174 | 0.038* | |
H9 | 0.5268 | 0.1391 | −0.0227 | 0.045* | |
H10 | 0.5773 | 0.1235 | 0.0886 | 0.045* | |
H11 | 0.5166 | 0.0891 | 0.2050 | 0.039* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F24 | 0.0521 (9) | 0.0728 (10) | 0.0336 (7) | 0.0233 (7) | 0.0135 (6) | 0.0123 (7) |
N1 | 0.0268 (8) | 0.0321 (9) | 0.0262 (8) | 0.0165 (7) | −0.0008 (7) | 0.0019 (7) |
N2A | 0.0248 (8) | 0.0245 (8) | 0.0250 (8) | 0.0134 (7) | −0.0006 (6) | −0.0002 (6) |
N7 | 0.0299 (9) | 0.0259 (8) | 0.0276 (9) | 0.0150 (7) | −0.0030 (7) | −0.0021 (7) |
C2 | 0.0271 (10) | 0.0249 (10) | 0.0263 (10) | 0.0125 (8) | −0.0023 (8) | −0.0022 (8) |
C21 | 0.0271 (10) | 0.0299 (10) | 0.0239 (9) | 0.0155 (8) | −0.0023 (8) | −0.0013 (8) |
C22 | 0.0379 (12) | 0.0325 (11) | 0.0319 (11) | 0.0143 (9) | −0.0020 (9) | −0.0049 (9) |
C23 | 0.0491 (13) | 0.0510 (14) | 0.0261 (11) | 0.0246 (12) | 0.0019 (10) | −0.0099 (10) |
C24 | 0.0330 (11) | 0.0520 (14) | 0.0252 (11) | 0.0201 (10) | 0.0050 (9) | 0.0087 (9) |
C25 | 0.0296 (11) | 0.0354 (11) | 0.0339 (11) | 0.0147 (9) | −0.0013 (9) | 0.0048 (9) |
C26 | 0.0287 (10) | 0.0294 (10) | 0.0302 (10) | 0.0151 (8) | −0.0038 (8) | −0.0040 (8) |
C2B | 0.0249 (9) | 0.0187 (9) | 0.0317 (10) | 0.0109 (8) | −0.0018 (8) | 0.0001 (7) |
C3 | 0.0293 (10) | 0.0289 (10) | 0.0340 (11) | 0.0156 (8) | 0.0017 (8) | 0.0023 (8) |
C4 | 0.0248 (10) | 0.0289 (10) | 0.0471 (13) | 0.0127 (9) | 0.0050 (9) | 0.0027 (9) |
C5 | 0.0250 (10) | 0.0283 (10) | 0.0498 (13) | 0.0116 (9) | −0.0062 (9) | 0.0003 (9) |
C6 | 0.0308 (10) | 0.0276 (10) | 0.0383 (11) | 0.0126 (9) | −0.0078 (9) | −0.0007 (9) |
C6A | 0.0271 (10) | 0.0212 (9) | 0.0326 (10) | 0.0115 (8) | −0.0025 (8) | −0.0019 (8) |
C7A | 0.0293 (10) | 0.0212 (9) | 0.0248 (10) | 0.0129 (8) | 0.0000 (8) | −0.0007 (7) |
C7B | 0.0282 (10) | 0.0227 (9) | 0.0255 (10) | 0.0129 (8) | 0.0009 (8) | −0.0022 (7) |
C8 | 0.0344 (11) | 0.0315 (11) | 0.0304 (11) | 0.0173 (9) | 0.0048 (8) | 0.0016 (8) |
C9 | 0.0353 (11) | 0.0366 (12) | 0.0361 (12) | 0.0152 (10) | 0.0099 (9) | 0.0001 (9) |
C10 | 0.0260 (10) | 0.0385 (12) | 0.0467 (13) | 0.0154 (9) | 0.0033 (9) | −0.0066 (10) |
C11 | 0.0292 (10) | 0.0342 (11) | 0.0353 (11) | 0.0171 (9) | −0.0029 (9) | −0.0032 (9) |
C11A | 0.0267 (10) | 0.0221 (9) | 0.0292 (10) | 0.0110 (8) | 0.0018 (8) | −0.0013 (8) |
Geometric parameters (Å, º) top
F24—C24 | 1.371 (2) | C2B—C3 | 1.392 (3) |
N1—C11A | 1.390 (2) | C2B—C6A | 1.400 (3) |
N1—C2 | 1.455 (2) | C3—C4 | 1.385 (3) |
N1—H1 | 0.93 | C3—H3 | 0.95 |
N2A—C7A | 1.372 (2) | C4—C5 | 1.389 (3) |
N2A—C2B | 1.391 (2) | C4—H4 | 0.95 |
N2A—C2 | 1.477 (2) | C5—C6 | 1.371 (3) |
N7—C7A | 1.319 (2) | C5—H5 | 0.95 |
N7—C6A | 1.390 (2) | C6—C6A | 1.394 (3) |
C2—C21 | 1.503 (3) | C6—H6 | 0.95 |
C2—H2 | 1.00 | C7A—C7B | 1.445 (3) |
C21—C22 | 1.385 (3) | C7B—C8 | 1.394 (3) |
C21—C26 | 1.390 (3) | C7B—C11A | 1.403 (3) |
C22—C23 | 1.387 (3) | C8—C9 | 1.381 (3) |
C22—H22 | 0.95 | C8—H8 | 0.95 |
C23—C24 | 1.365 (3) | C9—C10 | 1.391 (3) |
C23—H23 | 0.95 | C9—H9 | 0.95 |
C24—C25 | 1.359 (3) | C10—C11 | 1.381 (3) |
C25—C26 | 1.377 (3) | C10—H10 | 0.95 |
C25—H25 | 0.95 | C11—C11A | 1.396 (3) |
C26—H26 | 0.95 | C11—H11 | 0.95 |
| | | |
C11A—N1—C2 | 117.13 (15) | C4—C3—H3 | 121.7 |
C11A—N1—H1 | 120.6 | C2B—C3—H3 | 121.7 |
C2—N1—H1 | 107.5 | C3—C4—C5 | 121.85 (19) |
C7A—N2A—C2B | 106.98 (15) | C3—C4—H4 | 119.1 |
C7A—N2A—C2 | 121.27 (15) | C5—C4—H4 | 119.1 |
C2B—N2A—C2 | 130.35 (15) | C6—C5—C4 | 121.65 (19) |
C7A—N7—C6A | 104.87 (15) | C6—C5—H5 | 119.2 |
N1—C2—N2A | 106.08 (14) | C4—C5—H5 | 119.2 |
N1—C2—C21 | 109.94 (15) | C5—C6—C6A | 117.74 (19) |
N2A—C2—C21 | 112.77 (15) | C5—C6—H6 | 121.1 |
N1—C2—H2 | 109.3 | C6A—C6—H6 | 121.1 |
N2A—C2—H2 | 109.3 | N7—C6A—C6 | 128.91 (18) |
C21—C2—H2 | 109.3 | N7—C6A—C2B | 110.61 (16) |
C22—C21—C26 | 119.35 (18) | C6—C6A—C2B | 120.40 (18) |
C22—C21—C2 | 119.73 (17) | N7—C7A—N2A | 112.80 (16) |
C26—C21—C2 | 120.92 (17) | N7—C7A—C7B | 128.41 (17) |
C21—C22—C23 | 120.3 (2) | N2A—C7A—C7B | 118.75 (16) |
C21—C22—H22 | 119.8 | C8—C7B—C11A | 120.16 (18) |
C23—C22—H22 | 119.8 | C8—C7B—C7A | 122.42 (18) |
C24—C23—C22 | 117.8 (2) | C11A—C7B—C7A | 117.41 (16) |
C24—C23—H23 | 121.1 | C9—C8—C7B | 120.14 (19) |
C22—C23—H23 | 121.1 | C9—C8—H8 | 119.9 |
C25—C24—C23 | 123.85 (19) | C7B—C8—H8 | 119.9 |
C25—C24—F24 | 118.1 (2) | C8—C9—C10 | 119.59 (19) |
C23—C24—F24 | 118.04 (19) | C8—C9—H9 | 120.2 |
C24—C25—C26 | 118.00 (19) | C10—C9—H9 | 120.2 |
C24—C25—H25 | 121.0 | C11—C10—C9 | 121.05 (19) |
C26—C25—H25 | 121.0 | C11—C10—H10 | 119.5 |
C25—C26—C21 | 120.65 (18) | C9—C10—H10 | 119.5 |
C25—C26—H26 | 119.7 | C10—C11—C11A | 119.82 (19) |
C21—C26—H26 | 119.7 | C10—C11—H11 | 120.1 |
N2A—C2B—C3 | 133.53 (18) | C11A—C11—H11 | 120.1 |
N2A—C2B—C6A | 104.64 (16) | N1—C11A—C11 | 122.17 (17) |
C3—C2B—C6A | 121.79 (17) | N1—C11A—C7B | 118.51 (16) |
C4—C3—C2B | 116.57 (19) | C11—C11A—C7B | 119.24 (17) |
| | | |
C11A—N1—C2—N2A | 52.6 (2) | C7A—N7—C6A—C2B | −0.3 (2) |
C11A—N1—C2—C21 | 174.86 (15) | C5—C6—C6A—N7 | −175.52 (18) |
C7A—N2A—C2—N1 | −37.9 (2) | C5—C6—C6A—C2B | 0.8 (3) |
C2B—N2A—C2—N1 | 157.44 (17) | N2A—C2B—C6A—N7 | −1.63 (19) |
C7A—N2A—C2—C21 | −158.32 (15) | C3—C2B—C6A—N7 | 176.32 (16) |
C2B—N2A—C2—C21 | 37.0 (2) | N2A—C2B—C6A—C6 | −178.55 (16) |
N1—C2—C21—C22 | 120.81 (19) | C3—C2B—C6A—C6 | −0.6 (3) |
N2A—C2—C21—C22 | −121.04 (19) | C6A—N7—C7A—N2A | 2.3 (2) |
N1—C2—C21—C26 | −58.9 (2) | C6A—N7—C7A—C7B | −175.74 (17) |
N2A—C2—C21—C26 | 59.2 (2) | C2B—N2A—C7A—N7 | −3.4 (2) |
C26—C21—C22—C23 | 0.2 (3) | C2—N2A—C7A—N7 | −171.20 (15) |
C2—C21—C22—C23 | −179.48 (19) | C2B—N2A—C7A—C7B | 174.86 (16) |
C21—C22—C23—C24 | −0.7 (3) | C2—N2A—C7A—C7B | 7.0 (2) |
C22—C23—C24—C25 | 0.8 (3) | N7—C7A—C7B—C8 | 10.5 (3) |
C22—C23—C24—F24 | −178.83 (19) | N2A—C7A—C7B—C8 | −167.43 (17) |
C23—C24—C25—C26 | −0.4 (3) | N7—C7A—C7B—C11A | −168.53 (18) |
F24—C24—C25—C26 | 179.25 (18) | N2A—C7A—C7B—C11A | 13.5 (2) |
C24—C25—C26—C21 | −0.1 (3) | C11A—C7B—C8—C9 | 0.9 (3) |
C22—C21—C26—C25 | 0.2 (3) | C7A—C7B—C8—C9 | −178.13 (18) |
C2—C21—C26—C25 | 179.91 (17) | C7B—C8—C9—C10 | −0.3 (3) |
C7A—N2A—C2B—C3 | −174.7 (2) | C8—C9—C10—C11 | −0.2 (3) |
C2—N2A—C2B—C3 | −8.4 (3) | C9—C10—C11—C11A | 0.0 (3) |
C7A—N2A—C2B—C6A | 2.88 (18) | C2—N1—C11A—C11 | 146.28 (18) |
C2—N2A—C2B—C6A | 169.19 (17) | C2—N1—C11A—C7B | −36.9 (2) |
N2A—C2B—C3—C4 | 177.54 (19) | C10—C11—C11A—N1 | 177.31 (18) |
C6A—C2B—C3—C4 | 0.3 (3) | C10—C11—C11A—C7B | 0.5 (3) |
C2B—C3—C4—C5 | −0.2 (3) | C8—C7B—C11A—N1 | −177.87 (17) |
C3—C4—C5—C6 | 0.4 (3) | C7A—C7B—C11A—N1 | 1.2 (2) |
C4—C5—C6—C6A | −0.7 (3) | C8—C7B—C11A—C11 | −1.0 (3) |
C7A—N7—C6A—C6 | 176.26 (19) | C7A—C7B—C11A—C11 | 178.05 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N7i | 0.93 | 2.09 | 3.016 (3) | 173 |
C8—H8···F24ii | 0.95 | 2.49 | 3.274 (2) | 140 |
Symmetry codes: (i) −x+y+2/3, −x+1/3, z+1/3; (ii) −x+y+2/3, −x+1/3, z−2/3. |