Synthesis, crystal structure and Hirshfeld surface analysis of 3-(4,4-dimethyl-2,3,4,5-tetra­hydro-1H-1,5-benzodiazepin-2-yl­idene)-6-methyl-3,4-di­hydro-2H-pyran-2,4-dione

The title compound is built up from the benzodiazepine ring system linked to the pyridyl and pendant di­hydro­pyran rings. In the crystal, N—H...O and C—H...O hydrogen bonds link the mol­ecules into a three-dimensional network. A weak C—H ... π inter­action is also observed.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.112
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5       ..O2       .       2.72 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.021 Check

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         30 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         12 Info

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 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

---

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015b); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015a); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

3-(4,4-Dimethyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-ylidene)-6-methyl-3,4-dihydro-2H-pyran-2,4-dione

Crystal data

C17H18N2O3	F(000) = 632
Mr = 298.33	Dx = 1.300 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 5.5373 (1) Å	Cell parameters from 4280 reflections
b = 24.0197 (4) Å	θ = 3.8–71.5°
c = 11.7815 (3) Å	µ = 0.74 mm^−1
β = 103.488 (2)°	T = 296 K
V = 1523.77 (6) Å^3	Prism, yellow
Z = 4	0.42 × 0.38 × 0.16 mm

Data collection

Rigaku Oxford Diffraction diffractometer	2934 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	2519 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 16.0416 pixels mm^-1	θmax = 71.3°, θmin = 3.7°
ω scans	h = −5→6
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD 2015)	k = −27→29
Tmin = 0.700, Tmax = 1.000	l = −14→14
9860 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.040	w = 1/[σ^2(Fo^2) + (0.0578P)^2 + 0.3037P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.112	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.20 e Å^−3
2934 reflections	Δρmin = −0.16 e Å^−3
203 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015a), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0020 (3)
Primary atom site location: dual

Special details

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.

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

	x	y	z	Uiso*/Ueq
O1	0.9607 (2)	0.55040 (5)	0.34659 (11)	0.0620 (4)
O2	0.3736 (2)	0.69299 (4)	0.35380 (9)	0.0499 (3)
O3	0.45601 (19)	0.62933 (4)	0.48899 (9)	0.0430 (3)
N1	0.8514 (2)	0.61406 (5)	0.17042 (11)	0.0406 (3)
H1	0.9435	0.5909	0.2170	0.049*
N2	0.7655 (3)	0.71643 (5)	0.01003 (11)	0.0478 (3)
H2	0.7686	0.7426	−0.0394	0.057*
C1	0.6776 (2)	0.63806 (5)	0.21295 (12)	0.0350 (3)
C2	0.5128 (2)	0.67882 (6)	0.13633 (12)	0.0382 (3)
H2A	0.3856	0.6910	0.1752	0.046*
H2B	0.4303	0.6602	0.0648	0.046*
C3	0.6492 (2)	0.73059 (5)	0.10487 (11)	0.0342 (3)
C4	0.8700 (2)	0.66752 (6)	−0.01123 (12)	0.0377 (3)
C5	0.9507 (3)	0.66471 (7)	−0.11604 (14)	0.0491 (4)
H5	0.9191	0.6948	−0.1670	0.059*
C6	1.0733 (4)	0.61968 (8)	−0.14591 (17)	0.0644 (5)
H6	1.1245	0.6198	−0.2157	0.077*
C7	1.1215 (4)	0.57393 (8)	−0.0726 (2)	0.0733 (6)
H7	1.2073	0.5434	−0.0917	0.088*
C8	1.0400 (4)	0.57462 (7)	0.02874 (18)	0.0597 (5)
H8	1.0711	0.5439	0.0780	0.072*
C9	0.9117 (3)	0.62000 (6)	0.06068 (13)	0.0406 (3)
C10	0.6538 (2)	0.62144 (5)	0.32672 (12)	0.0355 (3)
C11	0.7997 (3)	0.57556 (6)	0.38662 (13)	0.0434 (3)
C12	0.7494 (3)	0.55810 (6)	0.49603 (13)	0.0483 (4)
H12	0.8365	0.5281	0.5357	0.058*
C13	0.5820 (3)	0.58377 (6)	0.54124 (13)	0.0429 (3)
C14	0.4890 (2)	0.65029 (5)	0.38391 (11)	0.0360 (3)
C15	0.5058 (4)	0.56883 (8)	0.65044 (15)	0.0594 (4)
H15A	0.5417	0.5993	0.7045	0.089*
H15B	0.5957	0.5364	0.6845	0.089*
H15C	0.3309	0.5611	0.6327	0.089*
C16	0.8401 (3)	0.75272 (6)	0.20995 (13)	0.0459 (4)
H16A	0.9684	0.7255	0.2348	0.069*
H16B	0.7605	0.7602	0.2725	0.069*
H16C	0.9118	0.7864	0.1888	0.069*
C17	0.4561 (3)	0.77557 (6)	0.05783 (13)	0.0457 (4)
H17A	0.5355	0.8065	0.0297	0.069*
H17B	0.3814	0.7880	0.1192	0.069*
H17C	0.3303	0.7605	−0.0049	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0764 (8)	0.0527 (7)	0.0685 (8)	0.0335 (6)	0.0406 (6)	0.0244 (6)
O2	0.0595 (7)	0.0469 (6)	0.0441 (6)	0.0227 (5)	0.0136 (5)	0.0028 (4)
O3	0.0484 (6)	0.0432 (5)	0.0407 (5)	0.0071 (4)	0.0171 (4)	0.0020 (4)
N1	0.0468 (7)	0.0331 (6)	0.0463 (7)	0.0048 (5)	0.0197 (5)	0.0062 (5)
N2	0.0655 (8)	0.0409 (6)	0.0456 (7)	0.0080 (6)	0.0304 (6)	0.0104 (5)
C1	0.0371 (7)	0.0296 (6)	0.0400 (7)	−0.0031 (5)	0.0122 (5)	0.0007 (5)
C2	0.0335 (6)	0.0443 (7)	0.0373 (7)	−0.0013 (5)	0.0095 (5)	0.0056 (6)
C3	0.0351 (7)	0.0353 (7)	0.0338 (6)	0.0037 (5)	0.0110 (5)	0.0048 (5)
C4	0.0371 (7)	0.0405 (7)	0.0375 (7)	−0.0075 (5)	0.0131 (5)	−0.0052 (5)
C5	0.0563 (9)	0.0541 (9)	0.0424 (8)	−0.0096 (7)	0.0225 (7)	−0.0055 (6)
C6	0.0835 (13)	0.0615 (10)	0.0630 (11)	−0.0134 (9)	0.0472 (10)	−0.0181 (9)
C7	0.0968 (15)	0.0455 (9)	0.0989 (15)	−0.0026 (9)	0.0660 (13)	−0.0179 (9)
C8	0.0756 (12)	0.0344 (7)	0.0830 (12)	−0.0005 (7)	0.0469 (10)	−0.0019 (7)
C9	0.0441 (7)	0.0350 (7)	0.0486 (8)	−0.0060 (5)	0.0223 (6)	−0.0053 (6)
C10	0.0395 (7)	0.0297 (6)	0.0389 (7)	0.0018 (5)	0.0125 (6)	0.0026 (5)
C11	0.0495 (8)	0.0355 (7)	0.0492 (8)	0.0087 (6)	0.0197 (6)	0.0079 (6)
C12	0.0584 (9)	0.0408 (7)	0.0483 (8)	0.0116 (6)	0.0178 (7)	0.0142 (6)
C13	0.0509 (8)	0.0389 (7)	0.0398 (7)	−0.0001 (6)	0.0128 (6)	0.0038 (6)
C14	0.0378 (7)	0.0342 (6)	0.0351 (6)	0.0023 (5)	0.0067 (5)	−0.0004 (5)
C15	0.0751 (11)	0.0606 (10)	0.0477 (9)	0.0014 (8)	0.0251 (8)	0.0077 (7)
C16	0.0445 (8)	0.0412 (8)	0.0490 (8)	0.0001 (6)	0.0048 (6)	−0.0002 (6)
C17	0.0462 (8)	0.0482 (8)	0.0437 (8)	0.0121 (6)	0.0127 (6)	0.0121 (6)

Geometric parameters (Å, º)

O1—C11	1.2569 (18)	C6—H6	0.9300
O2—C14	1.2167 (17)	C6—C7	1.385 (3)
O3—C13	1.3649 (18)	C7—H7	0.9300
O3—C14	1.3874 (16)	C7—C8	1.372 (3)
N1—H1	0.8600	C8—H8	0.9300
N1—C1	1.3168 (18)	C8—C9	1.400 (2)
N1—C9	1.4158 (18)	C10—C11	1.4487 (18)
N2—H2	0.8600	C10—C14	1.4331 (18)
N2—C3	1.4542 (17)	C11—C12	1.443 (2)
N2—C4	1.3584 (19)	C12—H12	0.9300
C1—C2	1.4907 (18)	C12—C13	1.324 (2)
C1—C10	1.4338 (18)	C13—C15	1.488 (2)
C2—H2A	0.9700	C15—H15A	0.9600
C2—H2B	0.9700	C15—H15B	0.9600
C2—C3	1.5444 (18)	C15—H15C	0.9600
C3—C16	1.524 (2)	C16—H16A	0.9600
C3—C17	1.5301 (18)	C16—H16B	0.9600
C4—C5	1.4094 (19)	C16—H16C	0.9600
C4—C9	1.408 (2)	C17—H17A	0.9600
C5—H5	0.9300	C17—H17B	0.9600
C5—C6	1.366 (2)	C17—H17C	0.9600
O1···N1	2.5351 (18)	C6···H2B^iv	2.95
O1···C12^i	3.379 (2)	C7···H2B^iv	2.92
O2···N2^ii	2.9990 (16)	C8···H2B^iv	2.94
O2···C2	2.8628 (17)	C9···H2B	2.85
O1···H12^i	2.45	C11···H1	2.35
O1···H1	1.79	C14···H2A	2.58
O2···H2A	2.12	C14···H17C^iii	2.95
O2···H2^ii	2.16	C16···O2^iv	3.3648 (19)
O2···H5^ii	2.72	H1···H8	2.24
O2···H17C^iii	2.91	H2···H5	2.21
N1···N2	3.0698 (17)	H2···H17A	2.27
N1···C16	3.3656 (19)	H2···H17C	2.59
N2···N1	3.0698 (17)	H2A···H17B	2.42
N1···H16A	2.8152	H2B···H17C	2.57
C4···C2^iv	3.5887 (17)	H5···H16B^v	2.42
C9···C2^iv	3.533 (2)	H5···H17B^v	2.51
C14···C17^iii	3.404 (2)	H12···H15B	2.45
C1···H16A	2.62	H12···H12^i	2.55
C4···H2B	2.79	H16A···O2^iv	2.48
C5···H2B^iv	2.99	H16B···H17B	2.52
C5···H16B^v	2.99	H16C···H17A	2.50
C13—O3—C14	122.24 (11)	C4—C9—N1	126.21 (12)
C1—N1—H1	114.6	C8—C9—N1	114.18 (14)
C1—N1—C9	130.71 (12)	C8—C9—C4	119.45 (14)
C9—N1—H1	114.6	C1—C10—C11	120.32 (12)
C3—N2—H2	115.5	C14—C10—C1	120.82 (12)
C4—N2—H2	115.5	C14—C10—C11	118.85 (12)
C4—N2—C3	128.91 (11)	O1—C11—C10	123.15 (13)
N1—C1—C2	117.10 (12)	O1—C11—C12	119.80 (13)
N1—C1—C10	117.94 (12)	C12—C11—C10	117.03 (12)
C10—C1—C2	124.90 (12)	C11—C12—H12	119.2
C1—C2—H2A	108.7	C13—C12—C11	121.53 (13)
C1—C2—H2B	108.7	C13—C12—H12	119.2
C1—C2—C3	114.17 (11)	O3—C13—C15	111.40 (13)
H2A—C2—H2B	107.6	C12—C13—O3	121.61 (13)
C3—C2—H2A	108.7	C12—C13—C15	126.99 (14)
C3—C2—H2B	108.7	O2—C14—O3	113.36 (12)
N2—C3—C2	108.97 (11)	O2—C14—C10	128.26 (13)
N2—C3—C16	110.99 (12)	O3—C14—C10	118.35 (11)
N2—C3—C17	106.51 (11)	C13—C15—H15A	109.5
C16—C3—C2	111.80 (11)	C13—C15—H15B	109.5
C16—C3—C17	109.98 (12)	C13—C15—H15C	109.5
C17—C3—C2	108.41 (11)	H15A—C15—H15B	109.5
N2—C4—C5	116.02 (13)	H15A—C15—H15C	109.5
N2—C4—C9	127.38 (12)	H15B—C15—H15C	109.5
C9—C4—C5	116.58 (13)	C3—C16—H16A	109.5
C4—C5—H5	118.6	C3—C16—H16B	109.5
C6—C5—C4	122.80 (16)	C3—C16—H16C	109.5
C6—C5—H5	118.6	H16A—C16—H16B	109.5
C5—C6—H6	119.9	H16A—C16—H16C	109.5
C5—C6—C7	120.20 (15)	H16B—C16—H16C	109.5
C7—C6—H6	119.9	C3—C17—H17A	109.5
C6—C7—H7	120.7	C3—C17—H17B	109.5
C8—C7—C6	118.58 (16)	C3—C17—H17C	109.5
C8—C7—H7	120.7	H17A—C17—H17B	109.5
C7—C8—H8	118.9	H17A—C17—H17C	109.5
C7—C8—C9	122.30 (17)	H17B—C17—H17C	109.5
C9—C8—H8	118.9
C9—N1—C1—C10	177.02 (13)	C1—N1—C9—C8	−157.26 (15)
C9—N1—C1—C2	−0.3 (2)	C1—N1—C9—C4	27.4 (2)
N1—C1—C2—C3	−63.12 (16)	N1—C1—C10—C14	172.65 (12)
C10—C1—C2—C3	119.73 (14)	C2—C1—C10—C14	−10.2 (2)
C4—N2—C3—C16	88.57 (18)	N1—C1—C10—C11	−6.4 (2)
C4—N2—C3—C17	−151.73 (15)	C2—C1—C10—C11	170.76 (13)
C4—N2—C3—C2	−35.0 (2)	C14—C10—C11—O1	−175.06 (15)
C1—C2—C3—N2	80.67 (14)	C1—C10—C11—O1	4.0 (2)
C1—C2—C3—C16	−42.38 (16)	C14—C10—C11—C12	6.4 (2)
C1—C2—C3—C17	−163.79 (12)	C1—C10—C11—C12	−174.60 (13)
C3—N2—C4—C9	−6.6 (3)	O1—C11—C12—C13	179.64 (16)
C3—N2—C4—C5	174.97 (14)	C10—C11—C12—C13	−1.7 (2)
N2—C4—C5—C6	175.76 (16)	C11—C12—C13—O3	−2.6 (3)
C9—C4—C5—C6	−2.8 (2)	C11—C12—C13—C15	177.58 (16)
C4—C5—C6—C7	0.6 (3)	C14—O3—C13—C12	2.2 (2)
C5—C6—C7—C8	1.1 (3)	C14—O3—C13—C15	−177.94 (13)
C6—C7—C8—C9	−0.4 (3)	C13—O3—C14—O2	−175.69 (13)
C7—C8—C9—C4	−1.9 (3)	C13—O3—C14—C10	2.60 (19)
C7—C8—C9—N1	−177.57 (18)	C1—C10—C14—O2	−7.8 (2)
N2—C4—C9—C8	−174.98 (16)	C11—C10—C14—O2	171.19 (14)
C5—C4—C9—C8	3.4 (2)	C1—C10—C14—O3	174.15 (12)
N2—C4—C9—N1	0.1 (2)	C11—C10—C14—O3	−6.81 (19)
C5—C4—C9—N1	178.49 (14)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x−1/2, −y+3/2, z+1/2; (iii) x+1/2, −y+3/2, z+1/2; (iv) x+1, y, z; (v) x+1/2, −y+3/2, z−1/2.

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.79	2.5351 (18)	143
N2—H2···O2^v	0.86	2.16	2.9990 (16)	166
C2—H2A···O2	0.97	2.12	2.8628 (17)	132
C5—H5···O2^v	0.93	2.72	3.453 (2)	136
C12—H12···O1^i	0.93	2.45	3.3789 (18)	174
C16—H16A···O2^iv	0.96	2.48	3.3646 (18)	154
C2—H2B···Cg^vi	0.97	2.63	3.4428 (15)	141

Symmetry codes: (i) −x+2, −y+1, −z+1; (iv) x+1, y, z; (v) x+1/2, −y+3/2, z−1/2; (vi) x−1, y, z.