6-(4-Fluoro­phenyl)-5,6-di­hydro­benzimidazo­[1,2-c]­quinazoline

The title compound, C₂₀H₁₄FN₃, 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.

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

---

Computing details

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

Crystal data

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) Å^3	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

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.162	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0894P)^2 + 1.7404P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N7^i	0.93	2.09	3.016 (3)	173
C8—H8···F24^ii	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.