10,10'-Methyl-enebis[2,3-dihydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-5,11(10H,11aH)-dione] dihydrate.

The organic mol-ecule and uncoordinated water mol-ecule in the crystal of the title compound, C(25)H(24)N(4)O(4)·2H(2)O, both lie on special positions of twofold symmetry. A twofold rotation axis passes through the methyl-ene C atom connecting the two dihydro-benzopyrrolodiazepindionyl parts. The seven-membered C(5)N(2) ring adopts a boat conformation.

Related literature

Pyrrolo[2,1-c][1,4]benzodiazepines are a group of potent chemicals produced by Streptomyces species. For their anti-cancer activity, see: Bose et al. (1992 ▶); Cargill et al. (1974 ▶); Gregson et al. (2004 ▶).

Experimental

Crystal data

C25H24N4O4·2H2O

M = 480.51

Trigonal,

a = 11.9901 (2) Å

c = 13.6054 (2) Å

V = 1693.90 (4) Å3

Z = 3

Mo Kα radiation

μ = 0.10 mm−1

T = 193 K

0.20 × 0.20 × 0.10 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: none

23041 measured reflections

1572 independent reflections

1472 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.126

S = 1.18

1572 reflections

159 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.48 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809040501/tk2545sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040501/tk2545Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C25H24N4O4·2H2O	Dx = 1.413 Mg m−3
Mr = 480.51	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P3121	Cell parameters from 9284 reflections
Hall symbol: P 31 2"	θ = 5.0–28.3°
a = 11.9901 (2) Å	µ = 0.10 mm−1
c = 13.6054 (2) Å	T = 193 K
V = 1693.90 (4) Å3	Block, colorless
Z = 3	0.20 × 0.20 × 0.10 mm
F(000) = 762

Bruker APEXII diffractometer	1472 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.043
graphite	θmax = 28.3°, θmin = 5.2°
φ and ω scans	h = −13→0
23041 measured reflections	k = 0→15
1572 independent reflections	l = 0→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.126	w = 1/[σ2(Fo2) + (0.0716P)2 + 0.3837P] where P = (Fo2 + 2Fc2)/3
S = 1.18	(Δ/σ)max = 0.001
1572 reflections	Δρmax = 0.46 e Å−3
159 parameters	Δρmin = −0.48 e Å−3
0 restraints	Absolute structure: nd
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.57170 (18)	0.14709 (17)	0.22350 (11)	0.0274 (4)
O2	0.7198 (2)	0.0623 (2)	0.57106 (13)	0.0362 (5)
O1W	0.9339 (4)	0.0162 (4)	0.5795 (2)	0.0819 (10)
H1W1	0.8758	0.0349	0.5692	0.123*
H1W2	1.0069	0.0798	0.5645	0.123*
N1	0.47771 (19)	0.1028 (2)	0.37359 (13)	0.0219 (4)
N2	0.7341 (2)	0.16144 (19)	0.42630 (14)	0.0235 (4)
C1	0.4814 (2)	0.1364 (2)	0.47532 (15)	0.0233 (5)
C2	0.3891 (3)	0.1666 (3)	0.50682 (18)	0.0303 (5)
H2	0.3310	0.1689	0.4606	0.036*
C3	0.3812 (3)	0.1934 (3)	0.60537 (19)	0.0361 (6)
H3	0.3195	0.2160	0.6261	0.043*
C4	0.4645 (3)	0.1867 (3)	0.67300 (18)	0.0382 (7)
H4	0.4581	0.2019	0.7407	0.046*
C5	0.5571 (3)	0.1577 (2)	0.64133 (16)	0.0303 (6)
H5	0.6133	0.1529	0.6882	0.036*
C6	0.5699 (2)	0.1355 (2)	0.54191 (16)	0.0243 (5)
C7	0.3561 (3)	0.0000	0.3333	0.0239 (6)
H7A	0.2900	−0.0353	0.3858	0.029*	0.50
H7B	0.3253	0.0353	0.2809	0.029*	0.50
C8	0.5813 (2)	0.1646 (2)	0.31219 (16)	0.0224 (5)
C9	0.7077 (2)	0.2487 (2)	0.36580 (15)	0.0225 (5)
H9	0.7020	0.3141	0.4078	0.027*
C10	0.8238 (2)	0.3128 (3)	0.29721 (17)	0.0296 (5)
H10A	0.8938	0.3930	0.3265	0.036*
H10B	0.7997	0.3332	0.2329	0.036*
C11	0.8645 (3)	0.2109 (3)	0.28641 (18)	0.0320 (6)
H11A	0.9549	0.2499	0.2641	0.038*
H11B	0.8080	0.1425	0.2397	0.038*
C12	0.8482 (3)	0.1579 (3)	0.39173 (18)	0.0317 (6)
H12A	0.8334	0.0690	0.3918	0.038*
H12B	0.9245	0.2133	0.4327	0.038*
C13	0.6801 (2)	0.1157 (2)	0.51428 (16)	0.0251 (5)

	U11	U22	U33	U12	U13	U23
O1	0.0330 (9)	0.0290 (9)	0.0170 (7)	0.0132 (8)	−0.0008 (6)	0.0000 (6)
O2	0.0427 (11)	0.0404 (11)	0.0284 (9)	0.0229 (9)	−0.0039 (8)	0.0068 (8)
O1W	0.082 (2)	0.126 (3)	0.0681 (18)	0.075 (2)	−0.0051 (16)	0.0110 (19)
N1	0.0235 (9)	0.0246 (9)	0.0173 (8)	0.0117 (8)	−0.0014 (7)	−0.0033 (7)
N2	0.0260 (10)	0.0253 (10)	0.0196 (8)	0.0131 (8)	−0.0018 (7)	0.0005 (7)
C1	0.0273 (11)	0.0201 (10)	0.0184 (9)	0.0088 (9)	0.0018 (9)	−0.0020 (8)
C2	0.0304 (13)	0.0304 (12)	0.0296 (12)	0.0148 (11)	0.0025 (9)	−0.0054 (10)
C3	0.0323 (13)	0.0361 (14)	0.0334 (13)	0.0122 (12)	0.0061 (11)	−0.0124 (11)
C4	0.0365 (15)	0.0363 (14)	0.0242 (11)	0.0050 (12)	0.0091 (11)	−0.0074 (10)
C5	0.0330 (13)	0.0259 (12)	0.0178 (10)	0.0042 (10)	0.0009 (9)	0.0005 (9)
C6	0.0267 (11)	0.0209 (10)	0.0181 (10)	0.0064 (9)	0.0014 (8)	−0.0009 (8)
C7	0.0248 (11)	0.0276 (16)	0.0203 (13)	0.0138 (8)	−0.0021 (6)	−0.0041 (12)
C8	0.0271 (11)	0.0212 (10)	0.0206 (10)	0.0134 (9)	−0.0005 (8)	0.0010 (8)
C9	0.0271 (11)	0.0212 (10)	0.0173 (9)	0.0106 (9)	−0.0013 (8)	0.0014 (8)
C10	0.0287 (12)	0.0278 (12)	0.0247 (10)	0.0084 (10)	0.0034 (9)	0.0017 (9)
C11	0.0294 (12)	0.0387 (14)	0.0277 (12)	0.0168 (11)	0.0022 (10)	−0.0014 (11)
C12	0.0299 (13)	0.0382 (14)	0.0287 (12)	0.0183 (11)	−0.0029 (10)	−0.0031 (10)
C13	0.0293 (12)	0.0227 (11)	0.0193 (9)	0.0099 (9)	−0.0037 (9)	0.0002 (8)

O1—C8	1.220 (3)	C5—C6	1.402 (3)
O2—C13	1.240 (3)	C5—H5	0.9500
O1W—H1W1	0.8429	C6—C13	1.502 (4)
O1W—H1W2	0.8500	C7—N1i	1.466 (3)
N1—C8	1.367 (3)	C7—H7A	0.9900
N1—C1	1.436 (3)	C7—H7B	0.9900
N1—C7	1.466 (3)	C8—C9	1.522 (3)
N2—C13	1.341 (3)	C9—C10	1.526 (3)
N2—C12	1.466 (3)	C9—H9	1.0000
N2—C9	1.485 (3)	C10—C11	1.533 (4)
C1—C2	1.393 (3)	C10—H10A	0.9900
C1—C6	1.399 (3)	C10—H10B	0.9900
C2—C3	1.393 (3)	C11—C12	1.540 (3)
C2—H2	0.9500	C11—H11A	0.9900
C3—C4	1.389 (4)	C11—H11B	0.9900
C3—H3	0.9500	C12—H12A	0.9900
C4—C5	1.387 (4)	C12—H12B	0.9900
C4—H4	0.9500
H1W1—O1W—H1W2	109.8	O1—C8—N1	121.9 (2)
C8—N1—C1	122.97 (19)	O1—C8—C9	124.4 (2)
C8—N1—C7	118.68 (17)	N1—C8—C9	113.59 (18)
C1—N1—C7	118.32 (17)	N2—C9—C8	106.93 (18)
C13—N2—C12	122.8 (2)	N2—C9—C10	103.41 (19)
C13—N2—C9	123.6 (2)	C8—C9—C10	113.32 (18)
C12—N2—C9	111.90 (18)	N2—C9—H9	111.0
C2—C1—C6	120.4 (2)	C8—C9—H9	111.0
C2—C1—N1	116.9 (2)	C10—C9—H9	111.0
C6—C1—N1	122.6 (2)	C9—C10—C11	103.3 (2)
C1—C2—C3	120.7 (2)	C9—C10—H10A	111.1
C1—C2—H2	119.6	C11—C10—H10A	111.1
C3—C2—H2	119.6	C9—C10—H10B	111.1
C4—C3—C2	119.4 (3)	C11—C10—H10B	111.1
C4—C3—H3	120.3	H10A—C10—H10B	109.1
C2—C3—H3	120.3	C10—C11—C12	102.4 (2)
C5—C4—C3	119.8 (2)	C10—C11—H11A	111.3
C5—C4—H4	120.1	C12—C11—H11A	111.3
C3—C4—H4	120.1	C10—C11—H11B	111.3
C4—C5—C6	121.6 (2)	C12—C11—H11B	111.3
C4—C5—H5	119.2	H11A—C11—H11B	109.2
C6—C5—H5	119.2	N2—C12—C11	102.4 (2)
C1—C6—C5	117.9 (2)	N2—C12—H12A	111.3
C1—C6—C13	124.7 (2)	C11—C12—H12A	111.3
C5—C6—C13	117.4 (2)	N2—C12—H12B	111.3
N1i—C7—N1	109.8 (3)	C11—C12—H12B	111.3
N1i—C7—H7A	109.7	H12A—C12—H12B	109.2
N1—C7—H7A	109.7	O2—C13—N2	122.4 (2)
N1i—C7—H7B	109.7	O2—C13—C6	121.4 (2)
N1—C7—H7B	109.7	N2—C13—C6	116.2 (2)
H7A—C7—H7B	108.2
C8—N1—C1—C2	124.6 (2)	C12—N2—C9—C8	113.4 (2)
C7—N1—C1—C2	−53.5 (3)	C13—N2—C9—C10	158.9 (2)
C8—N1—C1—C6	−57.4 (3)	C12—N2—C9—C10	−6.5 (2)
C7—N1—C1—C6	124.5 (2)	O1—C8—C9—N2	−112.1 (2)
C6—C1—C2—C3	−1.6 (4)	N1—C8—C9—N2	64.2 (2)
N1—C1—C2—C3	176.4 (2)	O1—C8—C9—C10	1.1 (3)
C1—C2—C3—C4	−1.6 (4)	N1—C8—C9—C10	177.5 (2)
C2—C3—C4—C5	2.1 (4)	N2—C9—C10—C11	29.1 (2)
C3—C4—C5—C6	0.4 (4)	C8—C9—C10—C11	−86.3 (2)
C2—C1—C6—C5	4.0 (3)	C9—C10—C11—C12	−40.6 (2)
N1—C1—C6—C5	−173.9 (2)	C13—N2—C12—C11	175.9 (2)
C2—C1—C6—C13	−174.4 (2)	C9—N2—C12—C11	−18.6 (3)
N1—C1—C6—C13	7.7 (4)	C10—C11—C12—N2	35.9 (2)
C4—C5—C6—C1	−3.4 (4)	C12—N2—C13—O2	−3.0 (4)
C4—C5—C6—C13	175.1 (2)	C9—N2—C13—O2	−166.9 (2)
C8—N1—C7—N1i	59.77 (17)	C12—N2—C13—C6	175.5 (2)
C1—N1—C7—N1i	−122.0 (2)	C9—N2—C13—C6	11.7 (3)
C1—N1—C8—O1	−169.7 (2)	C1—C6—C13—O2	−148.6 (2)
C7—N1—C8—O1	8.4 (3)	C5—C6—C13—O2	33.0 (3)
C1—N1—C8—C9	13.9 (3)	C1—C6—C13—N2	32.9 (3)
C7—N1—C8—C9	−168.02 (19)	C5—C6—C13—N2	−145.5 (2)
C13—N2—C9—C8	−81.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w1···O2	0.84	2.06	2.886 (4)	168