11-(4-Meth­oxy­phen­yl)-3,3-dimethyl-2,3,4,5,10,11-hexa­hydro-1H-dibenzo[b,e][1,4]diazepin-1-one monohydrate

Fadare, O.A.; Adelani, P.O.; Ikotun, A.A.; Obafemi, C.A.

doi:10.1107/S1600536812016194

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1508-o1509

doi:10.1107/S1600536812016194

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11-(4-Methoxyphenyl)-3,3-dimethyl-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one monohydrate

Olatomide A. Fadare,^a Pius O. Adelani,^b Adebomi A. Ikotun ^c and Craig A. Obafemi ^a ^*

^aChemistry Department, Obafemi Awolowo University, Ile-ife, Nigeria, ^bDepartment of Civil Engineering and Geological Sciences, and Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA, and ^cChemistry and Industrial Chemistry Department, Bowen University, Iwo, Nigeria
^*Correspondence e-mail: adeyemi01@yahoo.com

(Received 18 March 2012; accepted 13 April 2012; online 25 April 2012)

In the title compound, C₂₂H₂₄N₂O₂·H₂O, the co-crystallized water molecule interacts with the N and O atoms of the molecule through O_w—H⋯N, O_w—H⋯O(methyl) and N—H⋯O_w hydrogen-bonding interactions. These hydrogen bonds, along with the intermolecular N—H⋯O=C hydrogen-bonding interactions, connect the molecules 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_r = 366.45
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.043
wR(F²) = 0.106
S = 0.83
4529 reflections
257 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.16 e Å⁻³

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) -x+2, -y, -z; (ii) x+1, y, z; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812016194/ff2060sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812016194/ff2060Isup3.cml

checkCIF report

Comment top

Dibenzo[b,e][1,4]diazepinones are useful intermediates in the synthesis of pharmaceuticals. For example, dibenzo[b,e][1,4]diazepin-11-ones are useful intermediates in the preparation of dibenzo[1,4]diazepines (Hanze et al., 1963). They display wide variety of biological properties, including antidepressant (Beccalli et al., 2005), antimicrobial (Farnet et al., 2005), analgesic and anti-inflammatory (Joergensen et al., 1996), antitumor (McAlpine et al., 2008) activities, while the dibenzodiazepin-1-ones are hepatitis C virus (HCV) NS5B polymerase inhibitors (McGowan et al., 2009). In view of our interest in bioactivity of nitrogen-containing heterocyclic compounds (see: Ajani et al., 2010), we report here the microwave-assisted synthesis and the crystal structure of the title compound 1.

Related literature top

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 top

A mixture of dimedone (2.0 g, 14.3 mmol) and o-phenylenediamine (1.54 g, 14.3 mmol) in absolute ethanol (30 ml), containing acetic acid (0.5 ml), in a beaker was pulse irradiated in a microwave oven for 5 min. and left to stand at room temperature for 1 h. Anisaldehyde (1.95 g, 14.3 mmol) was added to the reaction mixture and then subjected to microwave irradiation for 5 min. (TLC monitored). Evaporation of the solvent afforded a gummy product. Cold aqueous ethanol was added with scratching to give yellow precipitate (melting point 202–205 ^o C). Crystals of 1 suitable for X-ray analysis were obtained by slow evaporation of ethanol solution of the product.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing the labelled atoms; thermal ellipsoids are drawn at the 20% probability level.
	Fig. 2. The packing diagram (ball and stick model) of the title compound, viewed along c-direction. Hydrogen bonds are drawn as dashed lines.
	Fig. 3. Reaction scheme of synthesis of the title compound.

11-(4-Methoxyphenyl)-3,3-dimethyl-2,3,4,5,10,11-hexahydro-1H- dibenzo[b,e][1,4]diazepin-1-one monohydrate top

Crystal data top

C₂₂H₂₄N₂O₂·H₂O	F(000) = 784
M_r = 366.45	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0442P)²] where P = (F_o² + 2F_c²)/3
S = 0.83	(Δ/σ)_max < 0.001
4529 reflections	Δρ_max = 0.19 e Å⁻³
257 parameters	Δρ_min = −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)

Crystal data top

C₂₂H₂₄N₂O₂·H₂O	V = 1986 (2) Å³
M_r = 366.45	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.684 (7) Å	µ = 0.08 mm⁻¹
b = 16.973 (12) Å	T = 296 K
c = 11.174 (8) Å	0.04 × 0.02 × 0.01 mm
β = 101.490 (9)°

Data collection top

Bruker APEXII CCD diffractometer	4529 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2187 reflections with I > 2σ(I)
T_min = 0.244, T_max = 0.323	R_int = 0.087
22692 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 0.83	Δρ_max = 0.19 e Å⁻³
4529 reflections	Δρ_min = −0.16 e Å⁻³
257 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y, −z; (ii) x+1, y, z; (iii) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₄N₂O₂·H₂O
M_r	366.45
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.684 (7), 16.973 (12), 11.174 (8)
β (°)	101.490 (9)
V (Å³)	1986 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.04 × 0.02 × 0.01

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.244, 0.323
No. of measured, independent and observed [I > 2σ(I)] reflections	22692, 4529, 2187
R_int	0.087
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.106, 0.83
No. of reflections	4529
No. of parameters	257
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.16

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y, −z; (ii) x+1, y, z; (iii) x, −y+1/2, z+1/2.

Acknowledgements

We thank the Central Science Laboratory, Obafemi Awolowo University, Ile-ife, for supporting this study.

References

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Volume 68| Part 5| May 2012| Pages o1508-o1509

doi:10.1107/S1600536812016194

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

11-(4-Meth­­oxy­phen­yl)-3,3-di­methyl-2,3,4,5,10,11-hexa­hydro-1H-dibenzo[b,e][1,4]diazepin-1-one monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

11-(4-Methoxyphenyl)-3,3-dimethyl-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one monohydrate