11-(4-Meth-oxy-phen-yl)-3,3-dimethyl-2,3,4,5,10,11-hexa-hydro-1H-dibenzo[b,e][1,4]diazepin-1-one monohydrate.

In the title compound, C(22)H(24)N(2)O(2)·H(2)O, the co-crystallized water mol-ecule inter-acts with the N and O atoms of the mol-ecule through O(w)-H⋯N, O(w)-H⋯O(meth-yl) and N-H⋯O(w) hydrogen-bonding inter-actions. These hydrogen bonds, along with the inter-molecular N-H⋯O=C hydrogen-bonding inter-actions, connect the mol-ecules into a three-dimensional network. The dihedral angle between the two aromatic rings is 65.46 (10)°.

Related literature

For details of the synthesis, see: Hanze et al. (1963 ▶); Rashed et al. (1993 ▶); Kolos et al. (2004 ▶); Cortés et al. (2007 ▶); Ajani et al. (2010 ▶). For the biological activity of dibenzo[b,e][1,4]diazepinones, see: Beccalli et al. (2005 ▶); Farnet et al. (2005 ▶); Joergensen et al. (1996 ▶); McAlpine et al. (2008 ▶); McGowan et al. (2009 ▶).

Experimental

Crystal data

C22H24N2O2·H2O

M = 366.45

Monoclinic,

a = 10.684 (7) Å

b = 16.973 (12) Å

c = 11.174 (8) Å

β = 101.490 (9)°

V = 1986 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.04 × 0.02 × 0.01 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.244, T max = 0.323

22692 measured reflections

4529 independent reflections

2187 reflections with I > 2σ(I)

R int = 0.087

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.106

S = 0.83

4529 reflections

257 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812016194/ff2060sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016194/ff2060Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812016194/ff2060Isup3.cml

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

C22H24N2O2·H2O	F(000) = 784
Mr = 366.45	Dx = 1.226 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2566 reflections
a = 10.684 (7) Å	θ = 2.2–21.4°
b = 16.973 (12) Å	µ = 0.08 mm−1
c = 11.174 (8) Å	T = 296 K
β = 101.490 (9)°	Rectangular tablet, light yellow
V = 1986 (2) Å3	0.04 × 0.02 × 0.01 mm
Z = 4

Bruker APEXII CCD diffractometer	4529 independent reflections
Radiation source: fine-focus sealed tube	2187 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.087
φ and ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −13→13
Tmin = 0.244, Tmax = 0.323	k = −21→22
22692 measured reflections	l = −14→14

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 atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0442P)2] where P = (Fo2 + 2Fc2)/3
S = 0.83	(Δ/σ)max < 0.001
4529 reflections	Δρmax = 0.19 e Å−3
257 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0082 (9)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.

	x	y	z	Uiso*/Ueq
N1	0.69308 (13)	−0.00644 (8)	0.04879 (12)	0.0381 (4)
H1A	0.6703	−0.0509	0.0142	0.046*
N2	0.68575 (13)	0.12181 (9)	0.21811 (13)	0.0341 (4)
H2C	0.6841 (17)	0.1561 (10)	0.2848 (17)	0.053 (6)*
O1	0.68552 (12)	0.26436 (7)	−0.07109 (11)	0.0459 (4)
O2	1.28931 (13)	0.17001 (10)	0.27104 (13)	0.0787 (5)
O1W	1.41964 (16)	0.15384 (8)	0.07513 (13)	0.0520 (4)
H1C	1.371 (2)	0.1659 (14)	0.140 (2)	0.104 (9)*
H1B	1.506 (3)	0.1427 (15)	0.120 (2)	0.124 (11)*
C1	0.66212 (16)	0.19349 (11)	−0.09321 (15)	0.0346 (4)
C2	0.59266 (18)	0.16858 (11)	−0.21814 (15)	0.0425 (5)
H2A	0.6057	0.2081	−0.2772	0.051*
H2B	0.5019	0.1661	−0.2186	0.051*
C3	0.63682 (17)	0.08909 (11)	−0.25676 (15)	0.0401 (5)
C4	0.61823 (18)	0.03053 (10)	−0.15837 (15)	0.0398 (5)
H4A	0.5275	0.0210	−0.1658	0.048*
H4B	0.6577	−0.0190	−0.1732	0.048*
C5	0.67258 (15)	0.05645 (10)	−0.02950 (15)	0.0318 (4)
C6	0.69591 (15)	0.13400 (10)	0.00061 (15)	0.0307 (4)
C7	0.77701 (19)	0.09265 (13)	−0.26960 (18)	0.0574 (6)
H7A	0.8292	0.1086	−0.1933	0.086*
H7B	0.7859	0.1300	−0.3318	0.086*
H7C	0.8036	0.0416	−0.2917	0.086*
C8	0.5557 (2)	0.06348 (13)	−0.37901 (17)	0.0596 (6)
H8A	0.4676	0.0610	−0.3724	0.089*
H8B	0.5832	0.0125	−0.4005	0.089*
H8C	0.5655	0.1009	−0.4410	0.089*
C9	0.74429 (16)	−0.01265 (10)	0.17528 (15)	0.0361 (4)
C10	0.74023 (16)	0.04797 (10)	0.25838 (15)	0.0349 (4)
C11	0.74741 (16)	0.16327 (10)	0.12753 (15)	0.0322 (4)
H11A	0.7198	0.2183	0.1283	0.039*
C12	0.79555 (19)	−0.08505 (11)	0.21730 (17)	0.0506 (5)
H12A	0.7985	−0.1254	0.1617	0.061*
C13	0.8421 (2)	−0.09834 (13)	0.33978 (19)	0.0606 (6)
H13A	0.8757	−0.1473	0.3666	0.073*
C14	0.8386 (2)	−0.03852 (13)	0.42190 (18)	0.0567 (6)
H14A	0.8694	−0.0469	0.5048	0.068*
C15	0.78916 (18)	0.03402 (11)	0.38124 (16)	0.0451 (5)
H15A	0.7886	0.0744	0.4374	0.054*
C16	0.89251 (16)	0.16503 (10)	0.16580 (15)	0.0319 (4)
C17	0.94955 (17)	0.19550 (11)	0.27789 (16)	0.0423 (5)
H17A	0.8978	0.2149	0.3290	0.051*
C18	1.08113 (18)	0.19834 (11)	0.31741 (17)	0.0439 (5)
H18A	1.1167	0.2191	0.3936	0.053*
C19	1.15759 (18)	0.17016 (13)	0.24243 (18)	0.0508 (5)
C20	1.1030 (2)	0.14011 (16)	0.1304 (2)	0.0809 (9)
H20A	1.1548	0.1213	0.0791	0.097*
C21	0.97209 (19)	0.13747 (14)	0.09301 (18)	0.0625 (7)
H21A	0.9370	0.1166	0.0168	0.075*
C22	1.35131 (19)	0.19213 (14)	0.38866 (18)	0.0643 (7)
H22A	1.4421	0.1892	0.3946	0.096*
H22B	1.3265	0.1572	0.4474	0.096*
H22C	1.3278	0.2451	0.4046	0.096*

	U11	U22	U33	U12	U13	U23
N1	0.0504 (10)	0.0309 (9)	0.0314 (9)	−0.0015 (7)	0.0045 (7)	−0.0035 (7)
N2	0.0364 (9)	0.0381 (9)	0.0299 (8)	−0.0002 (7)	0.0113 (7)	−0.0040 (7)
O1	0.0576 (9)	0.0375 (8)	0.0420 (8)	−0.0038 (7)	0.0082 (6)	0.0037 (6)
O2	0.0309 (8)	0.1414 (15)	0.0598 (11)	0.0007 (9)	−0.0007 (7)	−0.0285 (10)
O1W	0.0470 (9)	0.0548 (9)	0.0536 (10)	−0.0013 (7)	0.0083 (8)	−0.0027 (7)
C1	0.0310 (10)	0.0394 (11)	0.0342 (11)	−0.0007 (8)	0.0083 (8)	0.0025 (9)
C2	0.0436 (12)	0.0475 (12)	0.0343 (11)	−0.0036 (9)	0.0031 (9)	0.0068 (9)
C3	0.0414 (11)	0.0503 (12)	0.0273 (10)	−0.0052 (9)	0.0034 (8)	−0.0031 (9)
C4	0.0459 (11)	0.0398 (11)	0.0315 (10)	−0.0048 (9)	0.0026 (8)	−0.0033 (8)
C5	0.0302 (10)	0.0372 (11)	0.0277 (10)	−0.0007 (8)	0.0050 (8)	0.0011 (8)
C6	0.0273 (9)	0.0363 (11)	0.0285 (10)	0.0012 (8)	0.0055 (7)	0.0005 (8)
C7	0.0547 (14)	0.0787 (16)	0.0417 (12)	−0.0058 (12)	0.0164 (10)	−0.0086 (11)
C8	0.0718 (15)	0.0698 (15)	0.0315 (11)	−0.0090 (12)	−0.0035 (10)	−0.0008 (10)
C9	0.0406 (11)	0.0384 (11)	0.0289 (10)	−0.0023 (9)	0.0057 (8)	0.0017 (8)
C10	0.0337 (10)	0.0414 (11)	0.0301 (10)	−0.0037 (8)	0.0075 (8)	0.0003 (9)
C11	0.0325 (10)	0.0330 (10)	0.0317 (10)	0.0009 (8)	0.0076 (8)	−0.0014 (8)
C12	0.0680 (15)	0.0400 (12)	0.0413 (12)	0.0052 (10)	0.0053 (10)	0.0018 (10)
C13	0.0780 (17)	0.0504 (14)	0.0476 (14)	0.0080 (12)	−0.0010 (12)	0.0123 (11)
C14	0.0714 (16)	0.0598 (15)	0.0342 (12)	−0.0066 (12)	−0.0011 (10)	0.0102 (11)
C15	0.0541 (13)	0.0500 (13)	0.0298 (11)	−0.0085 (10)	0.0052 (9)	−0.0001 (9)
C16	0.0310 (10)	0.0342 (10)	0.0300 (10)	0.0004 (8)	0.0049 (8)	−0.0010 (8)
C17	0.0358 (11)	0.0522 (12)	0.0390 (12)	−0.0019 (9)	0.0077 (9)	−0.0100 (9)
C18	0.0419 (12)	0.0506 (12)	0.0367 (11)	−0.0049 (10)	0.0019 (9)	−0.0064 (9)
C19	0.0284 (11)	0.0751 (15)	0.0464 (13)	−0.0006 (10)	0.0017 (9)	−0.0082 (11)
C20	0.0339 (13)	0.153 (3)	0.0556 (15)	0.0073 (14)	0.0094 (11)	−0.0419 (15)
C21	0.0357 (12)	0.1076 (19)	0.0418 (13)	0.0026 (12)	0.0020 (10)	−0.0293 (12)
C22	0.0390 (13)	0.0911 (18)	0.0553 (15)	−0.0085 (12)	−0.0084 (11)	0.0041 (13)

N1—C5	1.370 (2)	C8—H8B	0.9600
N1—C9	1.414 (2)	C8—H8C	0.9600
N1—H1A	0.8600	C9—C12	1.389 (2)
N2—C10	1.417 (2)	C9—C10	1.392 (2)
N2—C11	1.490 (2)	C10—C15	1.388 (2)
N2—H2C	0.949 (19)	C11—C16	1.524 (2)
O1—C1	1.243 (2)	C11—H11A	0.9800
O2—C19	1.380 (2)	C12—C13	1.378 (3)
O2—C22	1.400 (2)	C12—H12A	0.9300
O1W—H1C	1.00 (3)	C13—C14	1.374 (3)
O1W—H1B	0.97 (3)	C13—H13A	0.9300
C1—C6	1.449 (2)	C14—C15	1.380 (3)
C1—C2	1.505 (2)	C14—H14A	0.9300
C2—C3	1.520 (3)	C15—H15A	0.9300
C2—H2A	0.9700	C16—C21	1.371 (2)
C2—H2B	0.9700	C16—C17	1.380 (2)
C3—C4	1.524 (2)	C17—C18	1.388 (3)
C3—C8	1.528 (2)	C17—H17A	0.9300
C3—C7	1.534 (3)	C18—C19	1.368 (3)
C4—C5	1.507 (2)	C18—H18A	0.9300
C4—H4A	0.9700	C19—C20	1.369 (3)
C4—H4B	0.9700	C20—C21	1.378 (3)
C5—C6	1.369 (2)	C20—H20A	0.9300
C6—C11	1.500 (2)	C21—H21A	0.9300
C7—H7A	0.9600	C22—H22A	0.9600
C7—H7B	0.9600	C22—H22B	0.9600
C7—H7C	0.9600	C22—H22C	0.9600
C8—H8A	0.9600
C5—N1—C9	132.62 (15)	C12—C9—N1	116.87 (16)
C5—N1—H1A	113.7	C10—C9—N1	123.65 (16)
C9—N1—H1A	113.7	C15—C10—C9	118.53 (17)
C10—N2—C11	115.11 (14)	C15—C10—N2	120.98 (16)
C10—N2—H2C	111.4 (11)	C9—C10—N2	120.48 (16)
C11—N2—H2C	108.9 (11)	N2—C11—C6	110.93 (14)
C19—O2—C22	119.15 (16)	N2—C11—C16	112.42 (14)
H1C—O1W—H1B	104 (2)	C6—C11—C16	115.65 (14)
O1—C1—C6	121.29 (16)	N2—C11—H11A	105.7
O1—C1—C2	119.90 (16)	C6—C11—H11A	105.7
C6—C1—C2	118.76 (16)	C16—C11—H11A	105.7
C1—C2—C3	112.89 (15)	C13—C12—C9	121.37 (19)
C1—C2—H2A	109.0	C13—C12—H12A	119.3
C3—C2—H2A	109.0	C9—C12—H12A	119.3
C1—C2—H2B	109.0	C14—C13—C12	119.3 (2)
C3—C2—H2B	109.0	C14—C13—H13A	120.3
H2A—C2—H2B	107.8	C12—C13—H13A	120.3
C2—C3—C4	106.36 (15)	C13—C14—C15	119.93 (19)
C2—C3—C8	110.71 (15)	C13—C14—H14A	120.0
C4—C3—C8	109.11 (16)	C15—C14—H14A	120.0
C2—C3—C7	110.83 (15)	C14—C15—C10	121.43 (18)
C4—C3—C7	111.29 (16)	C14—C15—H15A	119.3
C8—C3—C7	108.53 (16)	C10—C15—H15A	119.3
C5—C4—C3	114.71 (15)	C21—C16—C17	116.91 (17)
C5—C4—H4A	108.6	C21—C16—C11	122.92 (16)
C3—C4—H4A	108.6	C17—C16—C11	120.17 (15)
C5—C4—H4B	108.6	C16—C17—C18	122.55 (17)
C3—C4—H4B	108.6	C16—C17—H17A	118.7
H4A—C4—H4B	107.6	C18—C17—H17A	118.7
C6—C5—N1	126.45 (16)	C19—C18—C17	118.93 (18)
C6—C5—C4	122.15 (15)	C19—C18—H18A	120.5
N1—C5—C4	111.40 (15)	C17—C18—H18A	120.5
C5—C6—C1	119.04 (16)	C18—C19—C20	119.49 (19)
C5—C6—C11	124.43 (15)	C18—C19—O2	124.40 (18)
C1—C6—C11	116.42 (16)	C20—C19—O2	116.12 (18)
C3—C7—H7A	109.5	C19—C20—C21	120.7 (2)
C3—C7—H7B	109.5	C19—C20—H20A	119.6
H7A—C7—H7B	109.5	C21—C20—H20A	119.6
C3—C7—H7C	109.5	C16—C21—C20	121.38 (19)
H7A—C7—H7C	109.5	C16—C21—H21A	119.3
H7B—C7—H7C	109.5	C20—C21—H21A	119.3
C3—C8—H8A	109.5	O2—C22—H22A	109.5
C3—C8—H8B	109.5	O2—C22—H22B	109.5
H8A—C8—H8B	109.5	H22A—C22—H22B	109.5
C3—C8—H8C	109.5	O2—C22—H22C	109.5
H8A—C8—H8C	109.5	H22A—C22—H22C	109.5
H8B—C8—H8C	109.5	H22B—C22—H22C	109.5
C12—C9—C10	119.41 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1Wi	0.86	2.14	2.994 (3)	170
O1W—H1B···N2ii	0.98 (3)	2.04 (3)	3.020 (3)	178.2 (14)
O1W—H1C···O2	0.99 (2)	1.85 (2)	2.832 (3)	170 (2)
N2—H2C···O1iii	0.949 (18)	2.099 (18)	3.047 (3)	177.4 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1Wi	0.86	2.14	2.994 (3)	170
O1W—H1B⋯N2ii	0.98 (3)	2.04 (3)	3.020 (3)	178.2 (14)
O1W—H1C⋯O2	0.99 (2)	1.85 (2)	2.832 (3)	170 (2)
N2—H2C⋯O1iii	0.949 (18)	2.099 (18)	3.047 (3)	177.4 (13)

Symmetry codes: (i) ; (ii) ; (iii) .