Methyl 2-methyl-5-oxo-4-(2-thienyl)-1,5,7,8,9,10-hexa­hydro-4H-pyrido­[2′,3′:3,4]­pyrrolo­[1,2-a][1,3]­diazepine-3-carboxyl­ate

The crystal structure of the title compound, C₁₈H₁₉N₃O₃S, is formed by single mol­ecules linked by N—H...O hydrogen bonds into infinite linear chains along the ac diagonal. The thio­phene ring is nearly planar and is approximately perpendicular to the mean plane of the 1,4-di­hydro­pyridine ring. The ester group has a trans geometry with respect to the adjacent ring double bond. The di­hydro­pyridine and pyrrole rings are coplanar.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.058
• wR factor = 0.191
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C42    -   C43     ..      10.35 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C43    -   C44     ..       7.97 su

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S41    -   C41     ..       6.16 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C31     ..       6.00 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        S41
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C43
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C41

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: STADI4 (Stoe & Cie, 1991) and DIF4 (Stoe & Cie, 1991); cell refinement: STADI4 and DIF4; data reduction: REDU4 (Stoe & Cie, 1993); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Methyl 2-methyl-5-oxo-4-(2-thienyl)-1,5,7,8,9,10-hexahydro-4H- pyrido[2',3':3,4]pyrrolo[1,2-a][1,3]diazepine-3-carboxylate

Crystal data

C18H19N3O3S	F(000) = 752
Mr = 357.42	Dx = 1.363 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 43 reflections
a = 10.050 (3) Å	θ = 40.1–44.9°
b = 16.492 (5) Å	µ = 0.21 mm^−1
c = 10.737 (5) Å	T = 298 K
β = 101.94 (2)°	Prism, yellow
V = 1741.2 (11) Å^3	0.60 × 0.50 × 0.40 mm
Z = 4

Data collection

Stoe Stadi-4 diffractometer	2379 reflections with F^2 > 2σ(F^2)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 26.1°, θmin = 2.3°
profile data from θ/2θ scans	h = −12→12
Absorption correction: ψ scan (North et al., 1968)	k = 0→20
Tmin = 0.885, Tmax = 0.921	l = 0→13
3440 measured reflections	3 standard reflections every 120 min
3436 independent reflections	intensity decay: none

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.191	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0977P)^2 + 0.9592P] where P = (Fo^2 + 2Fc^2)/3
3436 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

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

	x	y	z	Uiso*/Ueq
S41	0.15313 (12)	0.21837 (9)	0.22074 (10)	0.0979 (4)
N1	0.1112 (2)	0.31172 (14)	0.5433 (2)	0.0470 (5)
H1	0.1698	0.3087	0.6139	0.056*
N6	−0.0997 (2)	0.13297 (14)	0.5031 (2)	0.0454 (5)
N71	0.0827 (2)	0.16296 (15)	0.6871 (2)	0.0498 (6)
O5	−0.2343 (2)	0.14951 (14)	0.30232 (19)	0.0628 (6)
O31	−0.0901 (3)	0.45074 (14)	0.1637 (2)	0.0756 (7)
O32	0.0784 (2)	0.51421 (14)	0.2909 (3)	0.0754 (7)
C2	0.1069 (3)	0.38010 (15)	0.4642 (3)	0.0464 (6)
C3	0.0230 (3)	0.38104 (16)	0.3462 (3)	0.0452 (6)
C4	−0.0574 (3)	0.30653 (16)	0.2881 (2)	0.0436 (6)
H4	−0.1506	0.3234	0.2505	0.052*
C5	−0.1430 (3)	0.17417 (17)	0.3881 (2)	0.0443 (6)
C7	0.0045 (2)	0.17772 (15)	0.5817 (2)	0.0399 (6)
C8	0.0218 (2)	0.25080 (15)	0.5065 (2)	0.0397 (5)
C9	−0.0619 (2)	0.24759 (15)	0.3920 (2)	0.0400 (6)
C21	0.2002 (4)	0.4459 (2)	0.5254 (3)	0.0686 (9)
H21A	0.1938	0.4913	0.4685	0.082*
H21B	0.2920	0.4261	0.5441	0.082*
H21C	0.1746	0.4626	0.6028	0.082*
C31	−0.0017 (3)	0.45093 (18)	0.2578 (3)	0.0543 (7)
C32	0.0493 (4)	0.5822 (2)	0.2038 (4)	0.0859 (12)
H32A	0.1113	0.6257	0.2334	0.103*
H32B	−0.0423	0.6003	0.1997	0.103*
H32C	0.0596	0.5656	0.1206	0.103*
C41	0.0053 (3)	0.27039 (17)	0.1849 (2)	0.0475 (6)
C42	−0.0480 (4)	0.27744 (19)	0.0449 (2)	0.0577 (8)
H42	−0.1268	0.3035	0.0032	0.069*
C43	0.0518 (6)	0.2341 (2)	−0.0118 (4)	0.0931 (14)
H43	0.0413	0.2289	−0.0995	0.112*
C44	0.1574 (5)	0.2028 (3)	0.0674 (4)	0.0904 (12)
H44	0.2270	0.1750	0.0408	0.108*
C61	−0.1916 (3)	0.0741 (2)	0.5450 (3)	0.0647 (8)
H61A	−0.2449	0.0477	0.4704	0.078*
H61B	−0.2543	0.1035	0.5861	0.078*
C62	−0.1233 (4)	0.0108 (2)	0.6338 (3)	0.0709 (9)
H62A	−0.0609	−0.0190	0.5929	0.085*
H62B	−0.1913	−0.0271	0.6505	0.085*
C63	−0.0439 (4)	0.0444 (2)	0.7617 (3)	0.0726 (9)
H63A	−0.1010	0.0831	0.7942	0.087*
H63B	−0.0245	0.0002	0.8223	0.087*
C64	0.0862 (4)	0.0848 (2)	0.7525 (3)	0.0646 (8)
H64A	0.1381	0.0922	0.8386	0.078*
H64B	0.1370	0.0473	0.7105	0.078*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S41	0.0912 (7)	0.1320 (11)	0.0700 (6)	0.0392 (7)	0.0156 (5)	−0.0126 (6)
N1	0.0497 (12)	0.0488 (13)	0.0373 (11)	−0.0064 (10)	−0.0031 (9)	0.0016 (10)
N6	0.0485 (11)	0.0473 (12)	0.0377 (11)	−0.0094 (10)	0.0026 (9)	0.0053 (9)
N71	0.0529 (12)	0.0557 (13)	0.0369 (11)	0.0015 (10)	0.0004 (10)	0.0075 (10)
O5	0.0614 (12)	0.0697 (14)	0.0475 (11)	−0.0203 (10)	−0.0111 (9)	0.0045 (10)
O31	0.0927 (16)	0.0542 (13)	0.0668 (14)	0.0028 (12)	−0.0140 (13)	0.0180 (11)
O32	0.0667 (13)	0.0600 (14)	0.0926 (17)	−0.0088 (11)	0.0007 (12)	0.0276 (13)
C2	0.0509 (14)	0.0388 (13)	0.0506 (15)	−0.0035 (11)	0.0132 (12)	−0.0038 (11)
C3	0.0491 (14)	0.0417 (14)	0.0460 (14)	0.0040 (11)	0.0125 (12)	0.0056 (11)
C4	0.0425 (13)	0.0480 (14)	0.0383 (13)	0.0028 (11)	0.0039 (10)	0.0075 (11)
C5	0.0442 (13)	0.0498 (14)	0.0364 (12)	−0.0022 (11)	0.0025 (11)	0.0024 (11)
C7	0.0425 (13)	0.0428 (13)	0.0337 (12)	−0.0008 (10)	0.0061 (10)	0.0007 (10)
C8	0.0431 (13)	0.0401 (13)	0.0354 (12)	0.0002 (10)	0.0068 (10)	0.0022 (10)
C9	0.0396 (12)	0.0465 (14)	0.0318 (12)	0.0002 (10)	0.0025 (10)	0.0031 (10)
C21	0.085 (2)	0.0564 (19)	0.0620 (19)	−0.0197 (17)	0.0088 (17)	−0.0079 (15)
C31	0.0517 (15)	0.0457 (15)	0.0644 (19)	0.0062 (12)	0.0098 (14)	0.0015 (13)
C32	0.067 (2)	0.061 (2)	0.125 (3)	−0.0015 (17)	0.010 (2)	0.038 (2)
C41	0.0572 (15)	0.0499 (15)	0.0343 (13)	−0.0043 (12)	0.0071 (11)	0.0065 (11)
C42	0.082 (2)	0.0600 (18)	0.0294 (13)	−0.0011 (15)	0.0069 (13)	0.0003 (12)
C43	0.166 (5)	0.077 (2)	0.0447 (18)	−0.011 (3)	0.040 (2)	−0.0068 (18)
C44	0.099 (3)	0.106 (3)	0.073 (3)	0.013 (3)	0.036 (2)	−0.013 (2)
C61	0.0641 (18)	0.0638 (19)	0.065 (2)	−0.0186 (15)	0.0112 (15)	0.0094 (15)
C62	0.073 (2)	0.0598 (19)	0.080 (2)	−0.0087 (16)	0.0175 (18)	0.0185 (17)
C63	0.087 (2)	0.075 (2)	0.0571 (19)	0.0017 (19)	0.0164 (17)	0.0251 (17)
C64	0.078 (2)	0.0630 (19)	0.0464 (16)	0.0045 (16)	−0.0013 (15)	0.0174 (14)

Geometric parameters (Å, º)

S41—C44	1.676 (4)	C21—H21A	0.9600
S41—C41	1.689 (3)	C21—H21B	0.9600
N1—C8	1.351 (3)	C21—H21C	0.9600
N1—C2	1.407 (3)	C32—H32A	0.9600
N1—H1	0.8600	C32—H32B	0.9600
N6—C5	1.398 (3)	C32—H32C	0.9600
N6—C7	1.410 (3)	C41—C42	1.492 (4)
N6—C61	1.473 (3)	C42—C43	1.463 (6)
N71—C7	1.261 (3)	C42—H42	0.9300
N71—C64	1.465 (4)	C43—C44	1.320 (6)
O5—C5	1.227 (3)	C43—H43	0.9300
O31—C31	1.200 (4)	C44—H44	0.9300
O32—C31	1.321 (4)	C61—C62	1.483 (5)
O32—C32	1.451 (4)	C61—H61A	0.9700
C2—C3	1.369 (4)	C61—H61B	0.9700
C2—C21	1.494 (4)	C62—C63	1.542 (5)
C3—C31	1.481 (4)	C62—H62A	0.9700
C3—C4	1.531 (4)	C62—H62B	0.9700
C4—C9	1.487 (3)	C63—C64	1.489 (5)
C4—C41	1.506 (4)	C63—H63A	0.9700
C4—H4	0.9800	C63—H63B	0.9700
C5—C9	1.456 (4)	C64—H64A	0.9700
C7—C8	1.481 (3)	C64—H64B	0.9700
C8—C9	1.339 (3)
C44—S41—C41	93.10 (19)	O32—C32—H32A	109.5
C8—N1—C2	119.0 (2)	O32—C32—H32B	109.5
C8—N1—H1	120.5	H32A—C32—H32B	109.5
C2—N1—H1	120.5	O32—C32—H32C	109.5
C5—N6—C7	109.3 (2)	H32A—C32—H32C	109.5
C5—N6—C61	119.3 (2)	H32B—C32—H32C	109.5
C7—N6—C61	126.7 (2)	C42—C41—C4	126.3 (3)
C7—N71—C64	123.3 (2)	C42—C41—S41	112.6 (2)
C31—O32—C32	114.0 (3)	C4—C41—S41	121.06 (19)
C3—C2—N1	120.2 (2)	C43—C42—C41	104.3 (3)
C3—C2—C21	127.5 (3)	C43—C42—H42	127.9
N1—C2—C21	112.3 (2)	C41—C42—H42	127.9
C2—C3—C31	126.3 (3)	C44—C43—C42	116.9 (3)
C2—C3—C4	122.7 (2)	C44—C43—H43	121.6
C31—C3—C4	111.0 (2)	C42—C43—H43	121.6
C9—C4—C41	112.0 (2)	C43—C44—S41	113.1 (3)
C9—C4—C3	108.3 (2)	C43—C44—H44	123.5
C41—C4—C3	110.6 (2)	S41—C44—H44	123.5
C9—C4—H4	108.6	N6—C61—C62	115.1 (3)
C41—C4—H4	108.6	N6—C61—H61A	108.5
C3—C4—H4	108.6	C62—C61—H61A	108.5
O5—C5—N6	123.4 (2)	N6—C61—H61B	108.5
O5—C5—C9	128.7 (2)	C62—C61—H61B	108.5
N6—C5—C9	108.0 (2)	H61A—C61—H61B	107.5
N71—C7—N6	133.1 (2)	C61—C62—C63	113.8 (3)
N71—C7—C8	121.7 (2)	C61—C62—H62A	108.8
N6—C7—C8	104.9 (2)	C63—C62—H62A	108.8
C9—C8—N1	123.4 (2)	C61—C62—H62B	108.8
C9—C8—C7	110.3 (2)	C63—C62—H62B	108.8
N1—C8—C7	126.3 (2)	H62A—C62—H62B	107.7
C8—C9—C5	107.5 (2)	C64—C63—C62	113.7 (3)
C8—C9—C4	123.5 (2)	C64—C63—H63A	108.8
C5—C9—C4	128.7 (2)	C62—C63—H63A	108.8
C2—C21—H21A	109.5	C64—C63—H63B	108.8
C2—C21—H21B	109.5	C62—C63—H63B	108.8
H21A—C21—H21B	109.5	H63A—C63—H63B	107.7
C2—C21—H21C	109.5	N71—C64—C63	119.4 (3)
H21A—C21—H21C	109.5	N71—C64—H64A	107.5
H21B—C21—H21C	109.5	C63—C64—H64A	107.5
O31—C31—O32	122.2 (3)	N71—C64—H64B	107.5
O31—C31—C3	122.3 (3)	C63—C64—H64B	107.5
O32—C31—C3	115.5 (3)	H64A—C64—H64B	107.0
C8—N1—C2—C3	−6.6 (4)	N6—C5—C9—C8	−2.3 (3)
C8—N1—C2—C21	173.0 (3)	O5—C5—C9—C4	−7.8 (5)
N1—C2—C3—C31	174.0 (2)	N6—C5—C9—C4	172.2 (2)
C21—C2—C3—C31	−5.6 (5)	C41—C4—C9—C8	105.4 (3)
N1—C2—C3—C4	−6.8 (4)	C3—C4—C9—C8	−16.8 (3)
C21—C2—C3—C4	173.6 (3)	C41—C4—C9—C5	−68.3 (3)
C2—C3—C4—C9	17.3 (3)	C3—C4—C9—C5	169.5 (2)
C31—C3—C4—C9	−163.5 (2)	C32—O32—C31—O31	0.0 (5)
C2—C3—C4—C41	−105.8 (3)	C32—O32—C31—C3	−178.6 (3)
C31—C3—C4—C41	73.4 (3)	C2—C3—C31—O31	−169.6 (3)
C7—N6—C5—O5	−179.0 (3)	C4—C3—C31—O31	11.2 (4)
C61—N6—C5—O5	−21.6 (4)	C2—C3—C31—O32	9.0 (4)
C7—N6—C5—C9	1.0 (3)	C4—C3—C31—O32	−170.2 (2)
C61—N6—C5—C9	158.4 (2)	C9—C4—C41—C42	134.6 (3)
C64—N71—C7—N6	4.4 (5)	C3—C4—C41—C42	−104.5 (3)
C64—N71—C7—C8	−167.9 (3)	C9—C4—C41—S41	−47.7 (3)
C5—N6—C7—N71	−172.7 (3)	C3—C4—C41—S41	73.2 (3)
C61—N6—C7—N71	32.0 (5)	C44—S41—C41—C42	0.1 (3)
C5—N6—C7—C8	0.5 (3)	C44—S41—C41—C4	−178.0 (3)
C61—N6—C7—C8	−154.8 (3)	C4—C41—C42—C43	178.3 (3)
C2—N1—C8—C9	7.5 (4)	S41—C41—C42—C43	0.4 (3)
C2—N1—C8—C7	−174.9 (2)	C41—C42—C43—C44	−0.9 (5)
N71—C7—C8—C9	172.1 (2)	C42—C43—C44—S41	1.1 (6)
N6—C7—C8—C9	−2.0 (3)	C41—S41—C44—C43	−0.7 (4)
N71—C7—C8—N1	−5.7 (4)	C5—N6—C61—C62	155.8 (3)
N6—C7—C8—N1	−179.9 (2)	C7—N6—C61—C62	−51.0 (4)
N1—C8—C9—C5	−179.4 (2)	N6—C61—C62—C63	62.8 (4)
C7—C8—C9—C5	2.6 (3)	C61—C62—C63—C64	−74.5 (4)
N1—C8—C9—C4	5.8 (4)	C7—N71—C64—C63	−44.8 (4)
C7—C8—C9—C4	−172.2 (2)	C62—C63—C64—N71	70.7 (4)
O5—C5—C9—C8	177.7 (3)