N'-[1-(2-Hy-droxy-phen-yl)ethyl-idene]-2-meth-oxy-benzohydrazide.

There are two independent mol-ecules in the asymmetric unit of the title compound, C(16)H(16)N(2)O(3), in which the dihedral angles between the two aromatic rings are 13.0 (3) and 6.4 (3)°. Intra-molecular O-H⋯N and N-H⋯O hydrogen bonds are observed in both mol-ecules, forming S(6) rings in all cases.

Related literature

For related structures, see: Lu et al. (2008a ▶,b ▶,c ▶); Xiao & Wei (2009 ▶); He (2008 ▶); Shi et al. (2007 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H16N2O3

M = 284.31

Monoclinic,

a = 11.5610 (12) Å

b = 10.8074 (11) Å

c = 22.544 (2) Å

β = 92.244 (5)°

V = 2814.6 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.20 × 0.17 × 0.17 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.981, T max = 0.984

16351 measured reflections

6065 independent reflections

3390 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.146

S = 1.01

6065 reflections

391 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.22 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 datablocks global, I. DOI: 10.1107/S1600536810020477/wn2390sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020477/wn2390Isup2.hkl

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

C16H16N2O3	F(000) = 1200
Mr = 284.31	Dx = 1.342 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.5610 (12) Å	Cell parameters from 3247 reflections
b = 10.8074 (11) Å	θ = 2.5–24.5°
c = 22.544 (2) Å	µ = 0.09 mm−1
β = 92.244 (5)°	T = 298 K
V = 2814.6 (5) Å3	Block, colourless
Z = 8	0.20 × 0.17 × 0.17 mm

Bruker APEXII CCD area-detector diffractometer	6065 independent reflections
Radiation source: fine-focus sealed tube	3390 reflections with I > 2σ(I)
graphite	Rint = 0.032
ω scans	θmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −14→14
Tmin = 0.981, Tmax = 0.984	k = −13→13
16351 measured reflections	l = −28→28

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0661P)2 + 0.2197P] where P = (Fo2 + 2Fc2)/3
6065 reflections	(Δ/σ)max < 0.001
391 parameters	Δρmax = 0.18 e Å−3
2 restraints	Δρmin = −0.22 e Å−3

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	0.32094 (13)	0.29578 (16)	0.92231 (7)	0.0578 (4)
N2	0.34893 (13)	0.35212 (17)	0.97530 (7)	0.0597 (4)
N3	0.16718 (12)	0.07857 (14)	0.00747 (7)	0.0541 (4)
N4	0.17677 (13)	0.16075 (15)	0.05364 (7)	0.0563 (4)
O1	0.17630 (13)	0.27945 (15)	0.83520 (7)	0.0765 (5)
H1	0.2056	0.3111	0.8652	0.115*
O2	0.21621 (14)	0.50002 (16)	0.95829 (7)	0.0969 (6)
O3	0.47037 (12)	0.36530 (14)	1.07416 (6)	0.0750 (4)
O4	0.23773 (13)	−0.12009 (15)	−0.03935 (7)	0.0826 (5)
H4	0.2346	−0.0665	−0.0137	0.124*
O5	0.31539 (14)	0.04667 (16)	0.10021 (7)	0.0888 (5)
O6	0.11005 (11)	0.36046 (13)	0.10849 (6)	0.0684 (4)
C1	0.33944 (15)	0.14134 (19)	0.85116 (8)	0.0549 (5)
C2	0.24499 (17)	0.1865 (2)	0.81688 (9)	0.0602 (5)
C3	0.2162 (2)	0.1340 (2)	0.76206 (10)	0.0767 (6)
H3	0.1532	0.1645	0.7397	0.092*
C4	0.2791 (2)	0.0384 (2)	0.74065 (10)	0.0797 (7)
H4A	0.2583	0.0035	0.7041	0.096*
C5	0.3730 (2)	−0.0064 (2)	0.77297 (10)	0.0780 (6)
H5	0.4165	−0.0709	0.7581	0.094*
C6	0.40240 (18)	0.0440 (2)	0.82710 (10)	0.0710 (6)
H6	0.4662	0.0127	0.8486	0.085*
C7	0.37168 (15)	0.1933 (2)	0.90977 (8)	0.0563 (5)
C8	0.45543 (18)	0.1287 (2)	0.95166 (9)	0.0759 (6)
H8A	0.5221	0.1802	0.9590	0.114*
H8B	0.4789	0.0519	0.9344	0.114*
H8C	0.4190	0.1126	0.9884	0.114*
C9	0.29454 (16)	0.4577 (2)	0.98954 (9)	0.0606 (5)
C10	0.33544 (15)	0.52031 (19)	1.04600 (8)	0.0569 (5)
C11	0.41947 (15)	0.4758 (2)	1.08692 (8)	0.0577 (5)
C12	0.44709 (18)	0.5422 (2)	1.13798 (9)	0.0729 (6)
H12	0.5020	0.5115	1.1654	0.087*
C13	0.3940 (2)	0.6530 (3)	1.14833 (11)	0.0827 (7)
H13	0.4127	0.6967	1.1829	0.099*
C14	0.3136 (2)	0.6999 (2)	1.10817 (12)	0.0865 (7)
H14	0.2788	0.7759	1.1150	0.104*
C15	0.28485 (19)	0.6335 (2)	1.05760 (11)	0.0733 (6)
H15	0.2300	0.6655	1.0305	0.088*
C16	0.56308 (19)	0.3193 (3)	1.11158 (10)	0.0882 (8)
H16A	0.6237	0.3799	1.1146	0.132*
H16B	0.5926	0.2444	1.0950	0.132*
H16C	0.5353	0.3026	1.1504	0.132*
C17	0.08689 (14)	0.00942 (18)	−0.08365 (8)	0.0505 (5)
C18	0.15800 (15)	−0.09596 (19)	−0.08333 (9)	0.0607 (5)
C19	0.14807 (18)	−0.1806 (2)	−0.12944 (11)	0.0790 (7)
H19	0.1947	−0.2508	−0.1284	0.095*
C20	0.07172 (17)	−0.1636 (2)	−0.17628 (10)	0.0748 (6)
H20	0.0673	−0.2208	−0.2071	0.090*
C21	0.00145 (18)	−0.0615 (2)	−0.17773 (10)	0.0701 (6)
H21	−0.0511	−0.0493	−0.2095	0.084*
C22	0.00875 (16)	0.0225 (2)	−0.13226 (9)	0.0627 (5)
H22	−0.0401	0.0909	−0.1337	0.075*
C23	0.09365 (15)	0.10144 (17)	−0.03562 (8)	0.0516 (5)
C24	0.01927 (17)	0.2152 (2)	−0.03747 (10)	0.0704 (6)
H24A	−0.0360	0.2105	−0.0069	0.106*
H24B	−0.0208	0.2209	−0.0755	0.106*
H24C	0.0670	0.2871	−0.0313	0.106*
C25	0.25190 (16)	0.1365 (2)	0.09986 (9)	0.0572 (5)
C26	0.25187 (15)	0.22604 (17)	0.15067 (8)	0.0524 (5)
C27	0.18211 (15)	0.33129 (18)	0.15560 (9)	0.0552 (5)
C28	0.18812 (18)	0.4015 (2)	0.20709 (10)	0.0680 (6)
H28	0.1409	0.4706	0.2105	0.082*
C29	0.2635 (2)	0.3694 (2)	0.25311 (10)	0.0747 (6)
H29	0.2664	0.4168	0.2876	0.090*
C30	0.33427 (19)	0.2686 (2)	0.24897 (10)	0.0744 (6)
H30	0.3862	0.2483	0.2800	0.089*
C31	0.32742 (17)	0.1977 (2)	0.19816 (9)	0.0640 (6)
H31	0.3749	0.1286	0.1956	0.077*
C32	0.0333 (2)	0.4636 (2)	0.11268 (11)	0.0884 (7)
H32A	−0.0163	0.4512	0.1453	0.133*
H32B	−0.0129	0.4708	0.0765	0.133*
H32C	0.0776	0.5379	0.1190	0.133*
H2	0.4078 (13)	0.330 (2)	1.0002 (8)	0.080*
H4B	0.1314 (15)	0.2279 (14)	0.0561 (9)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0546 (9)	0.0627 (11)	0.0555 (10)	0.0014 (8)	−0.0037 (8)	0.0059 (8)
N2	0.0567 (10)	0.0669 (11)	0.0546 (10)	0.0094 (9)	−0.0078 (8)	0.0061 (9)
N3	0.0520 (9)	0.0543 (10)	0.0559 (10)	0.0033 (8)	0.0014 (8)	0.0039 (8)
N4	0.0548 (9)	0.0540 (10)	0.0599 (10)	0.0068 (8)	−0.0006 (8)	0.0027 (9)
O1	0.0811 (10)	0.0791 (11)	0.0680 (10)	0.0200 (9)	−0.0146 (8)	0.0047 (8)
O2	0.0924 (11)	0.0879 (12)	0.1065 (12)	0.0312 (10)	−0.0459 (10)	−0.0091 (10)
O3	0.0696 (9)	0.0887 (11)	0.0652 (9)	0.0255 (8)	−0.0161 (7)	0.0016 (8)
O4	0.0723 (9)	0.0714 (10)	0.1018 (12)	0.0242 (8)	−0.0265 (9)	−0.0125 (9)
O5	0.0913 (11)	0.0879 (11)	0.0855 (11)	0.0431 (10)	−0.0196 (9)	−0.0160 (9)
O6	0.0639 (8)	0.0594 (9)	0.0810 (10)	0.0151 (7)	−0.0093 (7)	0.0014 (8)
C1	0.0500 (10)	0.0588 (12)	0.0562 (11)	−0.0027 (9)	0.0049 (9)	0.0117 (10)
C2	0.0605 (12)	0.0613 (13)	0.0590 (13)	0.0002 (11)	0.0038 (10)	0.0109 (10)
C3	0.0808 (15)	0.0853 (17)	0.0629 (14)	0.0030 (14)	−0.0124 (12)	0.0035 (13)
C4	0.0867 (16)	0.0848 (17)	0.0674 (14)	−0.0089 (14)	−0.0005 (13)	−0.0085 (13)
C5	0.0758 (15)	0.0801 (16)	0.0784 (15)	0.0034 (13)	0.0076 (13)	−0.0091 (13)
C6	0.0620 (12)	0.0771 (16)	0.0738 (15)	0.0055 (12)	0.0013 (11)	0.0023 (13)
C7	0.0484 (10)	0.0649 (13)	0.0557 (12)	0.0010 (10)	0.0036 (9)	0.0140 (10)
C8	0.0722 (14)	0.0903 (17)	0.0645 (13)	0.0219 (13)	−0.0069 (11)	0.0079 (12)
C9	0.0521 (11)	0.0626 (13)	0.0665 (13)	0.0036 (10)	−0.0057 (10)	0.0109 (11)
C10	0.0504 (10)	0.0592 (13)	0.0611 (12)	−0.0015 (10)	0.0018 (9)	0.0094 (10)
C11	0.0492 (11)	0.0680 (14)	0.0560 (12)	−0.0017 (10)	0.0051 (9)	0.0073 (10)
C12	0.0639 (13)	0.0939 (18)	0.0607 (13)	−0.0043 (13)	−0.0005 (10)	0.0002 (13)
C13	0.0853 (16)	0.0885 (19)	0.0746 (16)	−0.0078 (15)	0.0056 (13)	−0.0140 (14)
C14	0.0950 (18)	0.0719 (16)	0.0931 (18)	0.0080 (14)	0.0084 (15)	−0.0084 (15)
C15	0.0737 (14)	0.0649 (15)	0.0810 (16)	0.0070 (12)	−0.0010 (12)	0.0020 (12)
C16	0.0708 (14)	0.109 (2)	0.0834 (16)	0.0260 (14)	−0.0206 (12)	0.0132 (15)
C17	0.0426 (9)	0.0536 (11)	0.0557 (11)	−0.0009 (9)	0.0060 (8)	0.0085 (9)
C18	0.0443 (10)	0.0618 (13)	0.0758 (14)	0.0031 (10)	−0.0020 (10)	0.0009 (11)
C19	0.0604 (13)	0.0698 (15)	0.1064 (18)	0.0114 (12)	−0.0043 (13)	−0.0211 (14)
C20	0.0588 (13)	0.0823 (17)	0.0833 (16)	−0.0042 (12)	0.0015 (12)	−0.0186 (13)
C21	0.0653 (13)	0.0808 (16)	0.0640 (13)	−0.0014 (12)	−0.0014 (10)	0.0029 (12)
C22	0.0615 (12)	0.0649 (13)	0.0615 (12)	0.0060 (11)	0.0022 (10)	0.0097 (11)
C23	0.0459 (10)	0.0524 (11)	0.0569 (11)	0.0018 (9)	0.0082 (9)	0.0099 (9)
C24	0.0713 (13)	0.0676 (14)	0.0717 (14)	0.0174 (11)	−0.0035 (11)	0.0031 (11)
C25	0.0501 (11)	0.0600 (13)	0.0614 (12)	0.0036 (10)	−0.0003 (9)	0.0036 (10)
C26	0.0461 (10)	0.0505 (11)	0.0605 (12)	−0.0033 (9)	0.0023 (9)	0.0054 (10)
C27	0.0477 (10)	0.0529 (12)	0.0647 (12)	−0.0042 (9)	0.0003 (9)	0.0055 (10)
C28	0.0673 (13)	0.0553 (13)	0.0815 (15)	−0.0005 (11)	0.0033 (12)	−0.0061 (12)
C29	0.0824 (15)	0.0703 (15)	0.0708 (15)	−0.0098 (13)	−0.0035 (12)	−0.0101 (12)
C30	0.0778 (14)	0.0761 (16)	0.0679 (14)	−0.0004 (13)	−0.0138 (11)	0.0008 (13)
C31	0.0610 (12)	0.0641 (13)	0.0663 (13)	0.0025 (10)	−0.0038 (10)	0.0064 (11)
C32	0.0823 (15)	0.0685 (15)	0.113 (2)	0.0279 (13)	−0.0103 (14)	0.0000 (14)

N1—C7	1.290 (2)	C12—H12	0.9300
N1—N2	1.368 (2)	C13—C14	1.369 (3)
N2—C9	1.347 (3)	C13—H13	0.9300
N2—H2	0.896 (9)	C14—C15	1.377 (3)
N3—C23	1.289 (2)	C14—H14	0.9300
N3—N4	1.370 (2)	C15—H15	0.9300
N4—C25	1.356 (2)	C16—H16A	0.9600
N4—H4B	0.899 (9)	C16—H16B	0.9600
O1—C2	1.355 (2)	C16—H16C	0.9600
O1—H1	0.8200	C17—C22	1.400 (2)
O2—C9	1.215 (2)	C17—C18	1.405 (3)
O3—C11	1.367 (2)	C17—C23	1.470 (3)
O3—C16	1.427 (2)	C18—C19	1.386 (3)
O4—C18	1.352 (2)	C19—C20	1.362 (3)
O4—H4	0.8200	C19—H19	0.9300
O5—C25	1.217 (2)	C20—C21	1.370 (3)
O6—C27	1.361 (2)	C20—H20	0.9300
O6—C32	1.430 (2)	C21—C22	1.369 (3)
C1—C2	1.401 (3)	C21—H21	0.9300
C1—C6	1.401 (3)	C22—H22	0.9300
C1—C7	1.470 (3)	C23—C24	1.500 (3)
C2—C3	1.388 (3)	C24—H24A	0.9600
C3—C4	1.363 (3)	C24—H24B	0.9600
C3—H3	0.9300	C24—H24C	0.9600
C4—C5	1.372 (3)	C25—C26	1.499 (3)
C4—H4A	0.9300	C26—C31	1.389 (3)
C5—C6	1.367 (3)	C26—C27	1.401 (3)
C5—H5	0.9300	C27—C28	1.386 (3)
C6—H6	0.9300	C28—C29	1.373 (3)
C7—C8	1.498 (3)	C28—H28	0.9300
C8—H8A	0.9600	C29—C30	1.367 (3)
C8—H8B	0.9600	C29—H29	0.9300
C8—H8C	0.9600	C30—C31	1.378 (3)
C9—C10	1.502 (3)	C30—H30	0.9300
C10—C15	1.386 (3)	C31—H31	0.9300
C10—C11	1.399 (3)	C32—H32A	0.9600
C11—C12	1.383 (3)	C32—H32B	0.9600
C12—C13	1.370 (3)	C32—H32C	0.9600
C7—N1—N2	118.64 (16)	O3—C16—H16A	109.5
C9—N2—N1	119.21 (16)	O3—C16—H16B	109.5
C9—N2—H2	115.1 (14)	H16A—C16—H16B	109.5
N1—N2—H2	125.2 (14)	O3—C16—H16C	109.5
C23—N3—N4	118.66 (15)	H16A—C16—H16C	109.5
C25—N4—N3	119.30 (16)	H16B—C16—H16C	109.5
C25—N4—H4B	117.8 (14)	C22—C17—C18	116.45 (18)
N3—N4—H4B	122.7 (14)	C22—C17—C23	121.50 (17)
C2—O1—H1	109.5	C18—C17—C23	122.05 (17)
C11—O3—C16	119.98 (17)	O4—C18—C19	117.16 (18)
C18—O4—H4	109.5	O4—C18—C17	122.82 (19)
C27—O6—C32	119.43 (17)	C19—C18—C17	120.02 (19)
C2—C1—C6	116.99 (19)	C20—C19—C18	121.6 (2)
C2—C1—C7	121.85 (18)	C20—C19—H19	119.2
C6—C1—C7	121.17 (18)	C18—C19—H19	119.2
O1—C2—C3	116.81 (19)	C19—C20—C21	119.6 (2)
O1—C2—C1	122.93 (19)	C19—C20—H20	120.2
C3—C2—C1	120.2 (2)	C21—C20—H20	120.2
C4—C3—C2	120.8 (2)	C22—C21—C20	119.8 (2)
C4—C3—H3	119.6	C22—C21—H21	120.1
C2—C3—H3	119.6	C20—C21—H21	120.1
C3—C4—C5	120.1 (2)	C21—C22—C17	122.6 (2)
C3—C4—H4A	119.9	C21—C22—H22	118.7
C5—C4—H4A	119.9	C17—C22—H22	118.7
C6—C5—C4	119.8 (2)	N3—C23—C17	116.08 (16)
C6—C5—H5	120.1	N3—C23—C24	122.58 (18)
C4—C5—H5	120.1	C17—C23—C24	121.34 (16)
C5—C6—C1	122.0 (2)	C23—C24—H24A	109.5
C5—C6—H6	119.0	C23—C24—H24B	109.5
C1—C6—H6	119.0	H24A—C24—H24B	109.5
N1—C7—C1	115.04 (17)	C23—C24—H24C	109.5
N1—C7—C8	123.38 (19)	H24A—C24—H24C	109.5
C1—C7—C8	121.56 (19)	H24B—C24—H24C	109.5
C7—C8—H8A	109.5	O5—C25—N4	121.80 (19)
C7—C8—H8B	109.5	O5—C25—C26	121.87 (17)
H8A—C8—H8B	109.5	N4—C25—C26	116.32 (17)
C7—C8—H8C	109.5	C31—C26—C27	117.67 (18)
H8A—C8—H8C	109.5	C31—C26—C25	115.32 (17)
H8B—C8—H8C	109.5	C27—C26—C25	126.98 (17)
O2—C9—N2	121.67 (19)	O6—C27—C28	122.40 (18)
O2—C9—C10	121.6 (2)	O6—C27—C26	117.57 (18)
N2—C9—C10	116.69 (17)	C28—C27—C26	120.03 (18)
C15—C10—C11	117.8 (2)	C29—C28—C27	120.3 (2)
C15—C10—C9	115.91 (18)	C29—C28—H28	119.9
C11—C10—C9	126.25 (19)	C27—C28—H28	119.9
O3—C11—C12	122.77 (18)	C30—C29—C28	120.9 (2)
O3—C11—C10	117.10 (18)	C30—C29—H29	119.6
C12—C11—C10	120.1 (2)	C28—C29—H29	119.6
C13—C12—C11	120.3 (2)	C29—C30—C31	119.0 (2)
C13—C12—H12	119.8	C29—C30—H30	120.5
C11—C12—H12	119.8	C31—C30—H30	120.5
C14—C13—C12	120.6 (2)	C30—C31—C26	122.1 (2)
C14—C13—H13	119.7	C30—C31—H31	118.9
C12—C13—H13	119.7	C26—C31—H31	118.9
C13—C14—C15	119.3 (2)	O6—C32—H32A	109.5
C13—C14—H14	120.3	O6—C32—H32B	109.5
C15—C14—H14	120.3	H32A—C32—H32B	109.5
C14—C15—C10	121.8 (2)	O6—C32—H32C	109.5
C14—C15—H15	119.1	H32A—C32—H32C	109.5
C10—C15—H15	119.1	H32B—C32—H32C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.82	2.535 (2)	144
O4—H4···N3	0.82	1.82	2.541 (2)	145
N2—H2···O3	0.90 (1)	1.83 (2)	2.591 (2)	141 (2)
N4—H4B···O6	0.90 (1)	1.88 (2)	2.619 (2)	138 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.82	2.535 (2)	144
O4—H4⋯N3	0.82	1.82	2.541 (2)	145
N2—H2⋯O3	0.90 (1)	1.83 (2)	2.591 (2)	141 (2)
N4—H4B⋯O6	0.90 (1)	1.88 (2)	2.619 (2)	138 (2)