9-Phenyl-4,5-diaza-9H-fluoren-9-ol monohydrate

Yin, G.-J.; Yang, G.-B.; Wang, S.-M.

doi:10.1107/S1600536812021940

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1817

doi:10.1107/S1600536812021940

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9-Phenyl-4,5-diaza-9H-fluoren-9-ol monohydrate

Guo-Jie Yin,^a ^* Gang-Bin Yang ^a and Shi-Min Wang ^b

^aDepartment of Environment Engineering and Chemistry, Luoyang Institute of Science and Technology, 471023 Luoyang, People's Republic of China, and ^bChemistry Department, Zhengzhou University, 450052 Zhengzhou, People's Republic of China
^*Correspondence e-mail: yinguojie000000@yahoo.com.cn

(Received 30 March 2012; accepted 15 May 2012; online 19 May 2012)

The title compound, C₁₇H₁₂N₂O·H₂O, was synthesized by the reaction of 4,5-diazafluoren-9-one with a Grignard reagent in ether (the reaction mixture being hydrolysed with saturated NH₄Cl solution), and crystallizes with two organic molecules and two water molecules in the asymmetric unit. The 4,5-diazafluorene fragment is approximately planar, with r.m.s. deviations of 0.0448 and 0.0198 Å in the two molecules. The dihedral angles between the 4,5-diazafluorene planes and the phenyl ring are 80.49 (6) and 76.57 (7)°. The crystal packing features O—H⋯N and O—H⋯O hydrogen bonds involving the bridging solvent water molecules, which link the molecules into a three-dimensional network.

Related literature

For the synthesis of the title compound, see: Wong et al. (2001 ).

Experimental

Crystal data

C₁₇H₁₂N₂O·H₂O
M_r = 278.30
Triclinic, $[P \overline 1]$
a = 8.8703 (13) Å
b = 9.1691 (18) Å
c = 18.643 (3) Å
α = 86.745 (14)°
β = 86.943 (12)°
γ = 67.798 (16)°
V = 1400.8 (4) Å³
Z = 4
Cu Kα radiation
μ = 0.71 mm⁻¹
T = 291 K
0.24 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.848, T_max = 0.871
10727 measured reflections
4893 independent reflections
3755 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.151
S = 1.04
4893 reflections
375 parameters
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2	0.82	1.85	2.668 (2)	173
O3—H3A⋯O4ⁱ	0.82	1.89	2.705 (2)	174
O4—H4B⋯N3ⁱⁱ	0.85	2.01	2.839 (2)	164
O2—H2B⋯N2ⁱⁱⁱ	0.85	1.91	2.749 (2)	171
Symmetry codes: (i) x, y, z-1; (ii) -x, -y, -z+1; (iii) -x+2, -y, -z+1.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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 global, I. DOI: 10.1107/S1600536812021940/ez2292sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812021940/ez2292Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812021940/ez2292Isup3.cml

checkCIF report

Comment top

The title compound, containing two N atoms and a hydroxyl group, is a valuable intermediate in the preparation of medicinal compounds and an important ligand for the synthesis of functional metal-organic frameworks (MOFS). It was synthesized utilising a Grignard reagent to produce the target compound according to a literature reaction (Wong et al., 2001).

The title compound crystallizes with two molecules in the asymmetric unit, as shown in Fig. 1. Moreover, the 4,5-diazafluorene fragment is approximately planar, with r.m.s. deviations of 0.0448 Å and 0.0198 Å, respectively, and the dihedral angle between the 4,5-diazafluorene plane and the phenyl fragment are 80.49 (6)° and 76.57 (7)°. As shown in Fig. 2, due to the existence of the bridging solvent water molecules the crystal packing is stabilized through O—H···N and O—H···O hydrogen bonds, which link the molecules into a three-dimensional network.

Related literature top

For the synthesis of the title compound, see: Wong et al. (2001).

Experimental top

Reagents and solvents were of commercially available quality and the synthetic route (Wong et al., 2001) to the title compound is shown in Fig. 3. The Grignard reagents were prepared from magnesium powder (0.486 g, 20 mmol) in Et₂O (5 ml) and the corresponding arylbromide (20 mmol) in Et₂O (15 ml). The cooled Grignard solution was diluted with dry Et₂O (20 ml) and 4,5-diazafluoren-9-one (1.82 g, 10 mmol) was added to the Grignard solution. The mixture was refluxed for 2–6 h and then stirred for another 2 h at room temperature. The reaction mixture, was hydrolyzed with saturated NH₄Cl solution, extracted with Et₂O, washed with brine, dried over MgSO₄. Evaporation of the solvent under reduced pressure yielded the crude product. Purification was effected by column chromatography (SiO₂, EtOAc/Hexane = 1/5) and recrystallization from CH₂Cl₂ and hexane yielded colorless crystal.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 molecule of the title compound, with displacement ellipsoids for non-H atoms drawn at the 30% probability level.
	Fig. 2. A packing diagram of the title compound, viewed down the b axis, with hydrogen bonding shown as dashed lines.
	Fig. 3. The synthetic route to the title compound.

9-Phenyl-4,5-diaza-9H-fluoren-9-ol monohydrate top

Crystal data top

C₁₇H₁₂N₂O·H₂O	Z = 4
M_r = 278.30	F(000) = 584
Triclinic, P1	D_x = 1.320 Mg m⁻³
a = 8.8703 (13) Å	Cu Kα radiation, λ = 1.54184 Å
b = 9.1691 (18) Å	θ = 0.9–0.9°
c = 18.643 (3) Å	µ = 0.71 mm⁻¹
α = 86.745 (14)°	T = 291 K
β = 86.943 (12)°	Prismatic, colorless
γ = 67.798 (16)°	0.24 × 0.22 × 0.20 mm
V = 1400.8 (4) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	4893 independent reflections
Radiation source: fine-focus sealed tube	3755 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
phi and ω scans	θ_max = 66.6°, θ_min = 4.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −10→10
T_min = 0.848, T_max = 0.871	k = −10→9
10727 measured reflections	l = −22→20

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0787P)² + 0.165P] where P = (F_o² + 2F_c²)/3
4893 reflections	(Δ/σ)_max < 0.001
375 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₇H₁₂N₂O·H₂O	γ = 67.798 (16)°
M_r = 278.30	V = 1400.8 (4) Å³
Triclinic, P1	Z = 4
a = 8.8703 (13) Å	Cu Kα radiation
b = 9.1691 (18) Å	µ = 0.71 mm⁻¹
c = 18.643 (3) Å	T = 291 K
α = 86.745 (14)°	0.24 × 0.22 × 0.20 mm
β = 86.943 (12)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4893 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	3755 reflections with I > 2σ(I)
T_min = 0.848, T_max = 0.871	R_int = 0.034
10727 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 1.04	Δρ_max = 0.63 e Å⁻³
4893 reflections	Δρ_min = −0.37 e Å⁻³
375 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
O1	0.57816 (17)	0.33453 (18)	0.42450 (9)	0.0548 (4)
H1A	0.5908	0.2525	0.4479	0.082*
O3	0.2007 (2)	0.3172 (2)	0.04084 (9)	0.0590 (4)
H3A	0.1708	0.2943	0.0037	0.089*
N4	−0.1757 (2)	0.0898 (2)	0.10802 (11)	0.0527 (4)
N1	1.1101 (2)	−0.0146 (2)	0.37662 (12)	0.0560 (5)
C12	0.7024 (2)	0.4852 (2)	0.35363 (12)	0.0469 (5)
N2	1.1083 (2)	0.1802 (2)	0.50497 (11)	0.0550 (5)
C6	0.9881 (2)	0.2098 (2)	0.45896 (12)	0.0470 (5)
C5	0.9891 (2)	0.1169 (2)	0.39702 (12)	0.0465 (5)
N3	0.1634 (2)	−0.1697 (2)	0.07988 (11)	0.0535 (4)
C22	0.1298 (2)	−0.0174 (2)	0.08946 (11)	0.0461 (5)
C11	0.7318 (2)	0.3365 (2)	0.40160 (12)	0.0466 (5)
C4	0.8405 (2)	0.1867 (2)	0.36401 (12)	0.0477 (5)
C24	−0.0120 (2)	0.2490 (2)	0.10714 (11)	0.0452 (4)
C23	−0.0324 (2)	0.1074 (2)	0.10219 (11)	0.0451 (4)
C7	0.8388 (2)	0.3341 (2)	0.46360 (11)	0.0453 (4)
C28	0.1679 (2)	0.2274 (2)	0.09947 (12)	0.0474 (5)
C27	−0.3054 (3)	0.2230 (3)	0.11991 (14)	0.0596 (6)
H27	−0.4074	0.2162	0.1250	0.071*
C21	0.2462 (2)	0.0511 (2)	0.08844 (11)	0.0469 (5)
C25	−0.1472 (3)	0.3845 (3)	0.11780 (14)	0.0561 (5)
H25	−0.1385	0.4820	0.1201	0.067*
C29	0.2253 (2)	0.2752 (2)	0.16648 (12)	0.0476 (5)
C10	1.0747 (3)	0.2791 (3)	0.55871 (13)	0.0596 (6)
H10	1.1552	0.2628	0.5917	0.072*
C3	0.8106 (3)	0.1166 (3)	0.30651 (13)	0.0575 (5)
H3	0.7123	0.1595	0.2832	0.069*
C17	0.5615 (3)	0.6152 (3)	0.36287 (18)	0.0709 (7)
H17	0.4828	0.6115	0.3972	0.085*
C1	1.0770 (3)	−0.0803 (3)	0.32010 (15)	0.0611 (6)
H1	1.1571	−0.1726	0.3038	0.073*
C30	0.2676 (3)	0.1754 (3)	0.22721 (15)	0.0665 (6)
H30	0.2599	0.0770	0.2274	0.080*
C20	0.4076 (3)	−0.0435 (3)	0.07687 (14)	0.0579 (6)
H20	0.4888	−0.0024	0.0767	0.069*
C13	0.8185 (3)	0.4965 (3)	0.30300 (13)	0.0585 (5)
H13	0.9151	0.4098	0.2965	0.070*
C9	0.9288 (3)	0.4035 (3)	0.56844 (13)	0.0607 (6)
H9	0.9124	0.4673	0.6075	0.073*
C26	−0.2968 (3)	0.3690 (3)	0.12501 (15)	0.0625 (6)
H26	−0.3911	0.4569	0.1333	0.075*
C8	0.8065 (3)	0.4337 (3)	0.52010 (13)	0.0539 (5)
H8	0.7070	0.5173	0.5254	0.065*
C34	0.2348 (3)	0.4217 (3)	0.16785 (15)	0.0620 (6)
H34	0.2041	0.4912	0.1282	0.074*
C16	0.5362 (3)	0.7527 (3)	0.3209 (2)	0.0881 (10)
H16	0.4397	0.8395	0.3272	0.106*
C2	0.9330 (3)	−0.0211 (3)	0.28446 (14)	0.0623 (6)
H2	0.9180	−0.0732	0.2457	0.075*
C32	0.3354 (3)	0.3644 (4)	0.28715 (16)	0.0728 (8)
H32	0.3758	0.3932	0.3268	0.087*
C31	0.3208 (4)	0.2207 (4)	0.28722 (16)	0.0765 (8)
H31	0.3469	0.1536	0.3279	0.092*
C18	0.3210 (3)	−0.2570 (3)	0.06740 (15)	0.0625 (6)
H18	0.3487	−0.3634	0.0594	0.075*
C14	0.7941 (4)	0.6334 (3)	0.26199 (14)	0.0682 (7)
H14	0.8739	0.6386	0.2287	0.082*
C33	0.2895 (4)	0.4657 (3)	0.22770 (18)	0.0739 (7)
H33	0.2956	0.5647	0.2280	0.089*
C19	0.4451 (3)	−0.2013 (3)	0.06554 (16)	0.0674 (7)
H19	0.5525	−0.2686	0.0568	0.081*
C15	0.65056 (16)	0.76264 (14)	0.27072 (8)	0.0752 (8)
H15	0.6320	0.8548	0.2429	0.090*
O4	0.12630 (16)	0.23352 (14)	0.91460 (8)	0.0639 (4)
H4A	0.1958	0.1556	0.8933	0.077*
H4B	0.0329	0.2298	0.9103	0.077*
O2	0.61191 (16)	0.08322 (14)	0.51118 (8)	0.1338 (13)
H2A	0.5490	0.0608	0.5420	0.161*
H2B	0.7032	0.0086	0.5039	0.161*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0393 (7)	0.0561 (8)	0.0680 (10)	−0.0176 (6)	−0.0035 (7)	0.0057 (7)
O3	0.0694 (10)	0.0672 (10)	0.0527 (9)	−0.0409 (8)	−0.0022 (8)	0.0071 (7)
N4	0.0444 (9)	0.0561 (10)	0.0614 (11)	−0.0231 (8)	−0.0028 (8)	−0.0020 (8)
N1	0.0481 (9)	0.0473 (9)	0.0674 (12)	−0.0126 (8)	0.0029 (8)	−0.0026 (9)
C12	0.0439 (10)	0.0470 (10)	0.0501 (11)	−0.0167 (8)	−0.0089 (8)	−0.0005 (9)
N2	0.0476 (9)	0.0579 (10)	0.0601 (11)	−0.0207 (8)	−0.0108 (8)	0.0064 (9)
C6	0.0425 (10)	0.0480 (10)	0.0508 (11)	−0.0183 (8)	−0.0047 (8)	0.0058 (9)
C5	0.0424 (10)	0.0432 (10)	0.0535 (12)	−0.0163 (8)	−0.0005 (8)	0.0030 (9)
N3	0.0522 (10)	0.0471 (9)	0.0624 (11)	−0.0207 (8)	0.0016 (8)	−0.0012 (8)
C22	0.0451 (10)	0.0487 (11)	0.0449 (11)	−0.0187 (9)	−0.0006 (8)	0.0019 (8)
C11	0.0377 (9)	0.0475 (10)	0.0526 (12)	−0.0136 (8)	−0.0040 (8)	−0.0006 (9)
C4	0.0460 (10)	0.0446 (10)	0.0527 (12)	−0.0178 (8)	−0.0004 (9)	0.0011 (9)
C24	0.0442 (10)	0.0497 (11)	0.0440 (10)	−0.0203 (8)	−0.0068 (8)	0.0047 (8)
C23	0.0445 (10)	0.0505 (11)	0.0425 (10)	−0.0207 (8)	−0.0029 (8)	0.0020 (8)
C7	0.0412 (10)	0.0481 (10)	0.0468 (11)	−0.0176 (8)	−0.0009 (8)	0.0022 (8)
C28	0.0463 (10)	0.0510 (11)	0.0500 (11)	−0.0245 (9)	−0.0021 (8)	0.0027 (9)
C27	0.0399 (10)	0.0682 (14)	0.0724 (16)	−0.0220 (10)	−0.0043 (10)	−0.0030 (12)
C21	0.0462 (10)	0.0528 (11)	0.0443 (11)	−0.0219 (9)	0.0009 (8)	−0.0003 (9)
C25	0.0556 (12)	0.0486 (11)	0.0644 (14)	−0.0194 (10)	−0.0081 (10)	−0.0005 (10)
C29	0.0393 (9)	0.0532 (11)	0.0536 (12)	−0.0213 (8)	0.0005 (8)	−0.0023 (9)
C10	0.0610 (13)	0.0718 (15)	0.0536 (13)	−0.0333 (12)	−0.0128 (10)	0.0058 (11)
C3	0.0611 (13)	0.0555 (12)	0.0587 (14)	−0.0242 (10)	−0.0104 (10)	−0.0001 (10)
C17	0.0443 (11)	0.0556 (13)	0.106 (2)	−0.0134 (10)	0.0038 (12)	0.0110 (13)
C1	0.0630 (13)	0.0463 (11)	0.0705 (15)	−0.0170 (10)	0.0095 (11)	−0.0099 (11)
C30	0.0804 (17)	0.0634 (14)	0.0623 (15)	−0.0338 (13)	−0.0138 (13)	0.0038 (12)
C20	0.0456 (11)	0.0644 (13)	0.0646 (14)	−0.0232 (10)	0.0043 (10)	0.0019 (11)
C13	0.0656 (13)	0.0520 (12)	0.0546 (13)	−0.0190 (10)	0.0051 (10)	−0.0052 (10)
C9	0.0651 (14)	0.0745 (15)	0.0495 (12)	−0.0338 (12)	−0.0007 (10)	−0.0061 (11)
C26	0.0443 (11)	0.0578 (13)	0.0785 (17)	−0.0110 (10)	−0.0050 (11)	−0.0018 (12)
C8	0.0513 (11)	0.0561 (12)	0.0533 (12)	−0.0195 (9)	0.0040 (9)	−0.0054 (10)
C34	0.0651 (14)	0.0554 (13)	0.0695 (15)	−0.0269 (11)	−0.0035 (12)	−0.0042 (11)
C16	0.0540 (14)	0.0560 (14)	0.143 (3)	−0.0101 (12)	−0.0166 (17)	0.0245 (17)
C2	0.0764 (16)	0.0549 (13)	0.0598 (14)	−0.0290 (12)	0.0008 (12)	−0.0085 (11)
C32	0.0537 (13)	0.094 (2)	0.0728 (17)	−0.0255 (13)	−0.0082 (12)	−0.0264 (15)
C31	0.0817 (18)	0.0847 (19)	0.0600 (16)	−0.0257 (15)	−0.0219 (14)	0.0006 (14)
C18	0.0596 (13)	0.0492 (12)	0.0726 (16)	−0.0151 (10)	0.0071 (11)	−0.0011 (11)
C14	0.0915 (19)	0.0644 (15)	0.0554 (14)	−0.0379 (14)	0.0036 (13)	−0.0015 (11)
C33	0.0756 (16)	0.0710 (16)	0.086 (2)	−0.0376 (14)	−0.0002 (14)	−0.0241 (15)
C19	0.0484 (12)	0.0633 (14)	0.0816 (18)	−0.0131 (11)	0.0123 (11)	−0.0009 (12)
C15	0.0812 (18)	0.0612 (15)	0.087 (2)	−0.0315 (13)	−0.0240 (15)	0.0240 (14)
O4	0.0665 (10)	0.0683 (10)	0.0674 (11)	−0.0373 (8)	−0.0043 (8)	−0.0011 (8)
O2	0.0964 (17)	0.0766 (14)	0.195 (3)	−0.0078 (13)	0.0435 (19)	0.0445 (17)

Geometric parameters (Å, º) top

O1—C11	1.413 (2)	C10—H10	0.9300
O1—H1A	0.8200	C3—C2	1.385 (4)
O3—C28	1.415 (3)	C3—H3	0.9300
O3—H3A	0.8200	C17—C16	1.394 (4)
N4—C23	1.339 (3)	C17—H17	0.9300
N4—C27	1.343 (3)	C1—C2	1.376 (4)
N1—C5	1.334 (3)	C1—H1	0.9300
N1—C1	1.341 (3)	C30—C31	1.380 (4)
C12—C17	1.374 (3)	C30—H30	0.9300
C12—C13	1.388 (3)	C20—C19	1.383 (4)
C12—C11	1.531 (3)	C20—H20	0.9300
N2—C10	1.335 (3)	C13—C14	1.382 (4)
N2—C6	1.341 (3)	C13—H13	0.9300
C6—C7	1.385 (3)	C9—C8	1.384 (3)
C6—C5	1.471 (3)	C9—H9	0.9300
C5—C4	1.389 (3)	C26—H26	0.9300
N3—C22	1.334 (3)	C8—H8	0.9300
N3—C18	1.337 (3)	C34—C33	1.378 (4)
C22—C21	1.396 (3)	C34—H34	0.9300
C22—C23	1.478 (3)	C16—C15	1.368 (4)
C11—C7	1.528 (3)	C16—H16	0.9300
C11—C4	1.531 (3)	C2—H2	0.9300
C4—C3	1.368 (3)	C32—C31	1.372 (4)
C24—C25	1.377 (3)	C32—C33	1.379 (4)
C24—C23	1.386 (3)	C32—H32	0.9300
C24—C28	1.532 (3)	C31—H31	0.9300
C7—C8	1.380 (3)	C18—C19	1.377 (4)
C28—C29	1.520 (3)	C18—H18	0.9300
C28—C21	1.521 (3)	C14—C15	1.382 (3)
C27—C26	1.378 (3)	C14—H14	0.9300
C27—H27	0.9300	C33—H33	0.9300
C21—C20	1.377 (3)	C19—H19	0.9300
C25—C26	1.385 (3)	C15—H15	0.9300
C25—H25	0.9300	O4—H4A	0.8499
C29—C34	1.379 (3)	O4—H4B	0.8499
C29—C30	1.389 (3)	O2—H2A	0.8500
C10—C9	1.376 (4)	O2—H2B	0.8500

C11—O1—H1A	109.5	C4—C3—H3	121.5
C28—O3—H3A	109.5	C2—C3—H3	121.5
C23—N4—C27	114.86 (19)	C12—C17—C16	120.1 (3)
C5—N1—C1	114.2 (2)	C12—C17—H17	119.9
C17—C12—C13	118.2 (2)	C16—C17—H17	119.9
C17—C12—C11	119.8 (2)	N1—C1—C2	124.7 (2)
C13—C12—C11	121.89 (19)	N1—C1—H1	117.6
C10—N2—C6	115.3 (2)	C2—C1—H1	117.6
N2—C6—C7	124.5 (2)	C31—C30—C29	120.7 (2)
N2—C6—C5	126.85 (19)	C31—C30—H30	119.6
C7—C6—C5	108.60 (18)	C29—C30—H30	119.6
N1—C5—C4	125.3 (2)	C21—C20—C19	118.0 (2)
N1—C5—C6	126.14 (19)	C21—C20—H20	121.0
C4—C5—C6	108.49 (18)	C19—C20—H20	121.0
C22—N3—C18	115.15 (19)	C14—C13—C12	121.6 (2)
N3—C22—C21	124.5 (2)	C14—C13—H13	119.2
N3—C22—C23	127.28 (19)	C12—C13—H13	119.2
C21—C22—C23	108.21 (18)	C10—C9—C8	119.9 (2)
O1—C11—C7	113.44 (18)	C10—C9—H9	120.0
O1—C11—C12	107.74 (16)	C8—C9—H9	120.0
C7—C11—C12	109.78 (17)	C27—C26—C25	119.8 (2)
O1—C11—C4	113.06 (17)	C27—C26—H26	120.1
C7—C11—C4	100.59 (16)	C25—C26—H26	120.1
C12—C11—C4	112.20 (18)	C7—C8—C9	117.0 (2)
C3—C4—C5	119.0 (2)	C7—C8—H8	121.5
C3—C4—C11	130.0 (2)	C9—C8—H8	121.5
C5—C4—C11	110.99 (19)	C33—C34—C29	120.4 (3)
C25—C24—C23	119.08 (19)	C33—C34—H34	119.8
C25—C24—C28	129.28 (19)	C29—C34—H34	119.8
C23—C24—C28	111.64 (18)	C15—C16—C17	121.3 (2)
N4—C23—C24	124.93 (19)	C15—C16—H16	119.3
N4—C23—C22	126.92 (19)	C17—C16—H16	119.3
C24—C23—C22	108.14 (17)	C1—C2—C3	119.7 (2)
C8—C7—C6	119.0 (2)	C1—C2—H2	120.2
C8—C7—C11	129.77 (19)	C3—C2—H2	120.2
C6—C7—C11	111.19 (18)	C31—C32—C33	119.3 (2)
O3—C28—C29	106.99 (16)	C31—C32—H32	120.4
O3—C28—C21	112.36 (18)	C33—C32—H32	120.4
C29—C28—C21	112.57 (18)	C32—C31—C30	120.2 (3)
O3—C28—C24	112.88 (17)	C32—C31—H31	119.9
C29—C28—C24	111.63 (17)	C30—C31—H31	119.9
C21—C28—C24	100.50 (16)	N3—C18—C19	124.9 (2)
N4—C27—C26	124.2 (2)	N3—C18—H18	117.5
N4—C27—H27	117.9	C19—C18—H18	117.5
C26—C27—H27	117.9	C13—C14—C15	119.8 (2)
C20—C21—C22	118.6 (2)	C13—C14—H14	120.1
C20—C21—C28	129.95 (19)	C15—C14—H14	120.1
C22—C21—C28	111.49 (18)	C34—C33—C32	120.7 (3)
C24—C25—C26	117.1 (2)	C34—C33—H33	119.7
C24—C25—H25	121.5	C32—C33—H33	119.7
C26—C25—H25	121.5	C18—C19—C20	118.9 (2)
C34—C29—C30	118.6 (2)	C18—C19—H19	120.6
C34—C29—C28	119.7 (2)	C20—C19—H19	120.6
C30—C29—C28	121.70 (19)	C16—C15—C14	118.94 (18)
N2—C10—C9	124.2 (2)	C16—C15—H15	120.5
N2—C10—H10	117.9	C14—C15—H15	120.5
C9—C10—H10	117.9	H4A—O4—H4B	107.7
C4—C3—C2	117.1 (2)	H2A—O2—H2B	114.5

C10—N2—C6—C7	1.2 (3)	C23—N4—C27—C26	0.9 (4)
C10—N2—C6—C5	−177.4 (2)	N3—C22—C21—C20	−0.1 (3)
C1—N1—C5—C4	−1.1 (3)	C23—C22—C21—C20	−179.6 (2)
C1—N1—C5—C6	177.1 (2)	N3—C22—C21—C28	178.8 (2)
N2—C6—C5—N1	0.9 (3)	C23—C22—C21—C28	−0.8 (2)
C7—C6—C5—N1	−177.8 (2)	O3—C28—C21—C20	58.5 (3)
N2—C6—C5—C4	179.4 (2)	C29—C28—C21—C20	−62.3 (3)
C7—C6—C5—C4	0.6 (2)	C24—C28—C21—C20	178.8 (2)
C18—N3—C22—C21	−1.2 (3)	O3—C28—C21—C22	−120.1 (2)
C18—N3—C22—C23	178.3 (2)	C29—C28—C21—C22	118.99 (19)
C17—C12—C11—O1	26.8 (3)	C24—C28—C21—C22	0.1 (2)
C13—C12—C11—O1	−156.7 (2)	C23—C24—C25—C26	1.8 (3)
C17—C12—C11—C7	−97.1 (2)	C28—C24—C25—C26	−178.1 (2)
C13—C12—C11—C7	79.3 (3)	O3—C28—C29—C34	24.7 (3)
C17—C12—C11—C4	151.9 (2)	C21—C28—C29—C34	148.6 (2)
C13—C12—C11—C4	−31.7 (3)	C24—C28—C29—C34	−99.2 (2)
N1—C5—C4—C3	1.2 (3)	O3—C28—C29—C30	−155.8 (2)
C6—C5—C4—C3	−177.3 (2)	C21—C28—C29—C30	−31.9 (3)
N1—C5—C4—C11	−179.7 (2)	C24—C28—C29—C30	80.2 (3)
C6—C5—C4—C11	1.9 (2)	C6—N2—C10—C9	0.2 (3)
O1—C11—C4—C3	54.4 (3)	C5—C4—C3—C2	−0.4 (3)
C7—C11—C4—C3	175.7 (2)	C11—C4—C3—C2	−179.3 (2)
C12—C11—C4—C3	−67.7 (3)	C13—C12—C17—C16	1.4 (4)
O1—C11—C4—C5	−124.57 (19)	C11—C12—C17—C16	177.9 (3)
C7—C11—C4—C5	−3.3 (2)	C5—N1—C1—C2	0.3 (4)
C12—C11—C4—C5	113.3 (2)	C34—C29—C30—C31	−1.1 (4)
C27—N4—C23—C24	−0.4 (3)	C28—C29—C30—C31	179.4 (2)
C27—N4—C23—C22	179.7 (2)	C22—C21—C20—C19	1.2 (3)
C25—C24—C23—N4	−1.0 (3)	C28—C21—C20—C19	−177.4 (2)
C28—C24—C23—N4	178.9 (2)	C17—C12—C13—C14	−0.7 (4)
C25—C24—C23—C22	178.90 (19)	C11—C12—C13—C14	−177.2 (2)
C28—C24—C23—C22	−1.2 (2)	N2—C10—C9—C8	−1.0 (4)
N3—C22—C23—N4	1.6 (4)	N4—C27—C26—C25	−0.1 (4)
C21—C22—C23—N4	−178.9 (2)	C24—C25—C26—C27	−1.3 (4)
N3—C22—C23—C24	−178.3 (2)	C6—C7—C8—C9	1.1 (3)
C21—C22—C23—C24	1.2 (2)	C11—C7—C8—C9	−179.3 (2)
N2—C6—C7—C8	−1.9 (3)	C10—C9—C8—C7	0.2 (3)
C5—C6—C7—C8	176.88 (19)	C30—C29—C34—C33	1.8 (4)
N2—C6—C7—C11	178.37 (19)	C28—C29—C34—C33	−178.8 (2)
C5—C6—C7—C11	−2.8 (2)	C12—C17—C16—C15	−0.9 (5)
O1—C11—C7—C8	−55.0 (3)	N1—C1—C2—C3	0.4 (4)
C12—C11—C7—C8	65.6 (3)	C4—C3—C2—C1	−0.3 (4)
C4—C11—C7—C8	−176.0 (2)	C33—C32—C31—C30	2.8 (4)
O1—C11—C7—C6	124.70 (19)	C29—C30—C31—C32	−1.2 (5)
C12—C11—C7—C6	−114.7 (2)	C22—N3—C18—C19	1.4 (4)
C4—C11—C7—C6	3.7 (2)	C12—C13—C14—C15	−0.5 (4)
C25—C24—C28—O3	−59.5 (3)	C29—C34—C33—C32	−0.1 (4)
C23—C24—C28—O3	120.6 (2)	C31—C32—C33—C34	−2.2 (4)
C25—C24—C28—C29	61.0 (3)	N3—C18—C19—C20	−0.4 (4)
C23—C24—C28—C29	−118.9 (2)	C21—C20—C19—C18	−1.0 (4)
C25—C24—C28—C21	−179.4 (2)	C17—C16—C15—C14	−0.3 (4)
C23—C24—C28—C21	0.7 (2)	C13—C14—C15—C16	1.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2	0.82	1.85	2.668 (2)	173
O3—H3A···O4ⁱ	0.82	1.89	2.705 (2)	174
O4—H4B···N3ⁱⁱ	0.85	2.01	2.839 (2)	164
O2—H2B···N2ⁱⁱⁱ	0.85	1.91	2.749 (2)	171

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₂N₂O·H₂O
M_r	278.30
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	8.8703 (13), 9.1691 (18), 18.643 (3)
α, β, γ (°)	86.745 (14), 86.943 (12), 67.798 (16)
V (Å³)	1400.8 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.71
Crystal size (mm)	0.24 × 0.22 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.848, 0.871
No. of measured, independent and observed [I > 2σ(I)] reflections	10727, 4893, 3755
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.151, 1.04
No. of reflections	4893
No. of parameters	375
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.37

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), 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
O1—H1A···O2	0.82	1.85	2.668 (2)	172.5
O3—H3A···O4ⁱ	0.82	1.89	2.705 (2)	173.6
O4—H4B···N3ⁱⁱ	0.85	2.01	2.839 (2)	163.9
O2—H2B···N2ⁱⁱⁱ	0.85	1.91	2.749 (2)	170.7

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

Acknowledgements

This work was supported by a start-up grant from Luoyang Institute of Science and Technology.

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wong, K. T., Wang, Z. J., Chien, Y. Y. & Wang, C. L. (2001). Org. Lett. 15, 1037–1043. Google Scholar