1-Benzyl-4-phenyl-1H-1,5-benzodiazepin-2(3H)-one

In the title mol­ecule, C₂₂H₁₈N₂O, the seven-membered ring adopts a boat conformation with the planes of the pendant phenyl rings nearly perpendicular to the plane of the aromatic portion of the benzodiazepine core. Pairwise C—H...π(ring) inter­actions form inversion dimers which pack in zigzag layers associated through weak C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.044
• wR factor = 0.139
• Data-to-parameter ratio = 18.9

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         12 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   0 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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

1-Benzyl-4-phenyl-1H-1,5-benzodiazepin-2(3H)-one

Crystal data

C22H18N2O	F(000) = 688
Mr = 326.38	Dx = 1.258 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.6973 (7) Å	Cell parameters from 9683 reflections
b = 5.9179 (3) Å	θ = 2.4–27.5°
c = 19.8537 (9) Å	µ = 0.08 mm^−1
β = 93.461 (1)°	T = 296 K
V = 1723.67 (14) Å^3	Block, colourless
Z = 4	0.43 × 0.30 × 0.22 mm

Data collection

Bruker SMART APEX CCD diffractometer	4261 independent reflections
Radiation source: fine-focus sealed tube	3110 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 8.3333 pixels mm^-1	θmax = 28.3°, θmin = 2.1°
φ and ω scans	h = −19→19
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −7→7
Tmin = 0.87, Tmax = 0.98	l = −26→25
30265 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.139	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0823P)^2 + 0.065P] where P = (Fo^2 + 2Fc^2)/3
4261 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

Special details

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, collected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = –30.00 and 210.00°. The scan time was 15 sec/frame.

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. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.99 Å). All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.24295 (7)	0.5688 (2)	0.31026 (6)	0.0954 (4)
N1	0.40947 (6)	0.15215 (15)	0.42752 (5)	0.0473 (2)
N2	0.22089 (6)	0.26574 (17)	0.37616 (4)	0.0514 (3)
C1	0.24093 (7)	0.13976 (19)	0.43604 (5)	0.0458 (3)
C2	0.16861 (8)	0.0487 (2)	0.46964 (6)	0.0577 (3)
H2	0.1091	0.0767	0.4532	0.069*
C3	0.18363 (10)	−0.0813 (2)	0.52644 (7)	0.0663 (4)
H3	0.1346	−0.1407	0.5481	0.080*
C4	0.27189 (10)	−0.1238 (3)	0.55135 (7)	0.0663 (4)
H4	0.2823	−0.2090	0.5904	0.080*
C5	0.34419 (9)	−0.0404 (2)	0.51839 (6)	0.0565 (3)
H5	0.4033	−0.0731	0.5349	0.068*
C6	0.33060 (7)	0.09273 (18)	0.46054 (5)	0.0449 (3)
C7	0.41683 (7)	0.35018 (18)	0.40285 (6)	0.0459 (3)
C8	0.34347 (8)	0.5261 (2)	0.40845 (7)	0.0596 (3)
H8A	0.3241	0.5320	0.4543	0.071*
H8B	0.3663	0.6739	0.3968	0.071*
C9	0.26510 (8)	0.4603 (2)	0.36051 (7)	0.0602 (3)
C10	0.49709 (7)	0.40460 (19)	0.36411 (6)	0.0466 (3)
C11	0.53994 (8)	0.6133 (2)	0.36959 (7)	0.0624 (3)
H11	0.5181	0.7232	0.3980	0.075*
C12	0.61486 (9)	0.6586 (2)	0.33306 (8)	0.0720 (4)
H12	0.6442	0.7974	0.3379	0.086*
C13	0.64630 (8)	0.5000 (3)	0.28976 (7)	0.0673 (4)
H13	0.6957	0.5331	0.2643	0.081*
C14	0.60475 (8)	0.2924 (3)	0.28393 (6)	0.0627 (3)
H14	0.6264	0.1845	0.2548	0.075*
C15	0.53077 (7)	0.2438 (2)	0.32134 (6)	0.0522 (3)
H15	0.5034	0.1022	0.3178	0.063*
C16	0.14258 (8)	0.1991 (3)	0.33137 (6)	0.0593 (3)
H16A	0.1336	0.0375	0.3358	0.071*
H16B	0.1571	0.2284	0.2852	0.071*
C17	0.05352 (7)	0.3175 (2)	0.34414 (5)	0.0513 (3)
C18	0.04870 (9)	0.5022 (2)	0.38589 (7)	0.0662 (4)
H18	0.1013	0.5564	0.4088	0.079*
C19	−0.03416 (9)	0.6081 (3)	0.39392 (8)	0.0759 (4)
H19	−0.0369	0.7328	0.4223	0.091*
C20	−0.11235 (9)	0.5294 (3)	0.36009 (8)	0.0704 (4)
H20	−0.1677	0.6016	0.3651	0.084*
C21	−0.10814 (8)	0.3448 (3)	0.31912 (7)	0.0668 (4)
H21	−0.1609	0.2900	0.2966	0.080*
C22	−0.02581 (8)	0.2394 (2)	0.31100 (6)	0.0595 (3)
H22	−0.0236	0.1141	0.2829	0.071*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0594 (6)	0.1204 (9)	0.1077 (8)	0.0146 (6)	0.0168 (5)	0.0682 (8)
N1	0.0425 (5)	0.0469 (5)	0.0521 (5)	0.0025 (4)	−0.0001 (4)	−0.0024 (4)
N2	0.0423 (5)	0.0628 (6)	0.0491 (5)	0.0057 (4)	0.0040 (4)	0.0092 (4)
C1	0.0478 (6)	0.0463 (6)	0.0433 (6)	0.0023 (4)	0.0036 (4)	−0.0003 (4)
C2	0.0487 (6)	0.0674 (8)	0.0574 (7)	−0.0014 (5)	0.0064 (5)	0.0068 (6)
C3	0.0657 (8)	0.0745 (9)	0.0599 (8)	−0.0073 (7)	0.0126 (6)	0.0125 (7)
C4	0.0775 (9)	0.0708 (9)	0.0499 (7)	−0.0024 (7)	−0.0010 (6)	0.0141 (6)
C5	0.0583 (7)	0.0589 (7)	0.0510 (6)	0.0010 (5)	−0.0066 (5)	0.0023 (5)
C6	0.0467 (6)	0.0418 (5)	0.0458 (6)	0.0002 (4)	0.0011 (4)	−0.0044 (5)
C7	0.0418 (5)	0.0434 (6)	0.0524 (6)	0.0024 (4)	0.0010 (4)	−0.0064 (5)
C8	0.0548 (7)	0.0426 (6)	0.0835 (9)	0.0056 (5)	0.0222 (6)	−0.0005 (6)
C9	0.0434 (6)	0.0668 (8)	0.0720 (8)	0.0152 (5)	0.0177 (5)	0.0207 (7)
C10	0.0374 (5)	0.0482 (6)	0.0539 (6)	0.0029 (4)	−0.0006 (4)	−0.0008 (5)
C11	0.0507 (7)	0.0514 (7)	0.0857 (9)	−0.0045 (5)	0.0089 (6)	−0.0081 (6)
C12	0.0495 (7)	0.0635 (8)	0.1033 (11)	−0.0066 (6)	0.0073 (7)	0.0098 (8)
C13	0.0400 (6)	0.0891 (10)	0.0731 (8)	0.0042 (6)	0.0065 (5)	0.0194 (8)
C14	0.0490 (6)	0.0831 (9)	0.0564 (7)	0.0137 (6)	0.0056 (5)	−0.0032 (6)
C15	0.0456 (6)	0.0552 (7)	0.0554 (6)	0.0037 (5)	−0.0007 (5)	−0.0048 (5)
C16	0.0504 (6)	0.0810 (9)	0.0461 (6)	0.0112 (6)	0.0013 (5)	−0.0011 (6)
C17	0.0446 (6)	0.0645 (7)	0.0447 (6)	0.0044 (5)	0.0023 (4)	0.0066 (5)
C18	0.0435 (6)	0.0796 (9)	0.0752 (8)	0.0022 (6)	0.0003 (6)	−0.0129 (7)
C19	0.0575 (8)	0.0770 (9)	0.0942 (11)	0.0082 (7)	0.0112 (7)	−0.0135 (8)
C20	0.0439 (6)	0.0825 (10)	0.0852 (10)	0.0103 (6)	0.0087 (6)	0.0155 (8)
C21	0.0440 (6)	0.0875 (10)	0.0680 (8)	−0.0048 (6)	−0.0034 (5)	0.0127 (7)
C22	0.0543 (7)	0.0705 (8)	0.0531 (7)	−0.0039 (6)	−0.0012 (5)	0.0025 (6)

Geometric parameters (Å, º)

O1—C9	1.2139 (15)	C11—C12	1.3808 (18)
N1—C7	1.2773 (14)	C11—H11	0.9300
N1—C6	1.4103 (13)	C12—C13	1.372 (2)
N2—C9	1.3672 (16)	C12—H12	0.9300
N2—C1	1.4190 (14)	C13—C14	1.374 (2)
N2—C16	1.4653 (15)	C13—H13	0.9300
C1—C2	1.3969 (16)	C14—C15	1.3836 (17)
C1—C6	1.4048 (15)	C14—H14	0.9300
C2—C3	1.3719 (18)	C15—H15	0.9300
C2—H2	0.9300	C16—C17	1.5193 (16)
C3—C4	1.383 (2)	C16—H16A	0.9700
C3—H3	0.9300	C16—H16B	0.9700
C4—C5	1.3731 (19)	C17—C18	1.3766 (18)
C4—H4	0.9300	C17—C22	1.3832 (17)
C5—C6	1.3971 (16)	C18—C19	1.3873 (18)
C5—H5	0.9300	C18—H18	0.9300
C7—C10	1.4820 (15)	C19—C20	1.377 (2)
C7—C8	1.5078 (15)	C19—H19	0.9300
C8—C9	1.5007 (19)	C20—C21	1.366 (2)
C8—H8A	0.9700	C20—H20	0.9300
C8—H8B	0.9700	C21—C22	1.3795 (18)
C10—C15	1.3865 (15)	C21—H21	0.9300
C10—C11	1.3879 (17)	C22—H22	0.9300
C7—N1—C6	119.87 (9)	C12—C11—H11	119.9
C9—N2—C1	123.75 (10)	C10—C11—H11	119.9
C9—N2—C16	117.08 (10)	C13—C12—C11	120.40 (13)
C1—N2—C16	118.87 (10)	C13—C12—H12	119.8
C2—C1—C6	118.89 (10)	C11—C12—H12	119.8
C2—C1—N2	118.52 (10)	C12—C13—C14	119.99 (12)
C6—C1—N2	122.49 (10)	C12—C13—H13	120.0
C3—C2—C1	121.31 (12)	C14—C13—H13	120.0
C3—C2—H2	119.3	C13—C14—C15	120.03 (12)
C1—C2—H2	119.3	C13—C14—H14	120.0
C2—C3—C4	119.79 (12)	C15—C14—H14	120.0
C2—C3—H3	120.1	C14—C15—C10	120.48 (12)
C4—C3—H3	120.1	C14—C15—H15	119.8
C5—C4—C3	120.02 (12)	C10—C15—H15	119.8
C5—C4—H4	120.0	N2—C16—C17	115.33 (10)
C3—C4—H4	120.0	N2—C16—H16A	108.4
C4—C5—C6	121.21 (11)	C17—C16—H16A	108.4
C4—C5—H5	119.4	N2—C16—H16B	108.4
C6—C5—H5	119.4	C17—C16—H16B	108.4
C5—C6—C1	118.75 (10)	H16A—C16—H16B	107.5
C5—C6—N1	116.23 (9)	C18—C17—C22	118.64 (11)
C1—C6—N1	124.74 (10)	C18—C17—C16	122.87 (11)
N1—C7—C10	119.13 (9)	C22—C17—C16	118.47 (11)
N1—C7—C8	121.86 (10)	C17—C18—C19	120.36 (12)
C10—C7—C8	118.90 (10)	C17—C18—H18	119.8
C9—C8—C7	107.40 (10)	C19—C18—H18	119.8
C9—C8—H8A	110.2	C20—C19—C18	120.24 (14)
C7—C8—H8A	110.2	C20—C19—H19	119.9
C9—C8—H8B	110.2	C18—C19—H19	119.9
C7—C8—H8B	110.2	C21—C20—C19	119.65 (12)
H8A—C8—H8B	108.5	C21—C20—H20	120.2
O1—C9—N2	121.64 (14)	C19—C20—H20	120.2
O1—C9—C8	122.78 (13)	C20—C21—C22	120.21 (12)
N2—C9—C8	115.56 (10)	C20—C21—H21	119.9
C15—C10—C11	118.80 (11)	C22—C21—H21	119.9
C15—C10—C7	119.57 (10)	C21—C22—C17	120.89 (13)
C11—C10—C7	121.63 (10)	C21—C22—H22	119.6
C12—C11—C10	120.27 (13)	C17—C22—H22	119.6
C9—N2—C1—C2	139.33 (12)	C7—C8—C9—N2	66.58 (13)
C16—N2—C1—C2	−34.13 (15)	N1—C7—C10—C15	38.62 (15)
C9—N2—C1—C6	−44.34 (16)	C8—C7—C10—C15	−137.79 (12)
C16—N2—C1—C6	142.19 (11)	N1—C7—C10—C11	−141.23 (12)
C6—C1—C2—C3	1.24 (19)	C8—C7—C10—C11	42.37 (16)
N2—C1—C2—C3	177.70 (12)	C15—C10—C11—C12	−0.15 (19)
C1—C2—C3—C4	0.1 (2)	C7—C10—C11—C12	179.70 (11)
C2—C3—C4—C5	−1.5 (2)	C10—C11—C12—C13	1.6 (2)
C3—C4—C5—C6	1.6 (2)	C11—C12—C13—C14	−1.8 (2)
C4—C5—C6—C1	−0.32 (18)	C12—C13—C14—C15	0.5 (2)
C4—C5—C6—N1	−174.53 (12)	C13—C14—C15—C10	1.00 (18)
C2—C1—C6—C5	−1.09 (17)	C11—C10—C15—C14	−1.16 (17)
N2—C1—C6—C5	−177.40 (10)	C7—C10—C15—C14	178.99 (10)
C2—C1—C6—N1	172.58 (11)	C9—N2—C16—C17	−81.50 (13)
N2—C1—C6—N1	−3.73 (17)	C1—N2—C16—C17	92.40 (13)
C7—N1—C6—C5	−140.63 (11)	N2—C16—C17—C18	11.36 (18)
C7—N1—C6—C1	45.55 (15)	N2—C16—C17—C22	−170.31 (11)
C6—N1—C7—C10	−175.68 (9)	C22—C17—C18—C19	−0.5 (2)
C6—N1—C7—C8	0.61 (16)	C16—C17—C18—C19	177.85 (13)
N1—C7—C8—C9	−73.35 (14)	C17—C18—C19—C20	−0.1 (2)
C10—C7—C8—C9	102.95 (11)	C18—C19—C20—C21	0.7 (2)
C1—N2—C9—O1	−176.47 (11)	C19—C20—C21—C22	−0.8 (2)
C16—N2—C9—O1	−2.89 (17)	C20—C21—C22—C17	0.2 (2)
C1—N2—C9—C8	4.97 (16)	C18—C17—C22—C21	0.41 (19)
C16—N2—C9—C8	178.55 (9)	C16—C17—C22—C21	−177.99 (12)
C7—C8—C9—O1	−111.96 (14)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1^i	0.93	2.47	3.2808 (17)	145
C4—H4···Cg1^ii	0.93	2.98	3.767 (2)	143

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y, −z+1.