3-tert-Butyl-4-oxo-3,4-dihydro-phthalazin-1-yl 3,5-dimethyl-benzoate.

The title compound, C(21)H(22)N(2)O(3), was synthesized by the reaction of tert-butyl-hydrazine with phthalic anhydride and further O-benzoyl-ation of the resulting inter-mediate by 3,5-dimethyl-benzoyl chloride. Inter-molecular C-H⋯O=C inter-actions link the mol-ecules into layers.

Related literature

For ecdysone agonists, see: Wing (1988 ▶). For the synthesis, see: Hou et al. (2002 ▶). For C—N bond lengths, see: Sasada (1984 ▶).

Experimental

Crystal data

C21H22N2O3

M = 350.41

Monoclinic,

a = 8.7974 (2) Å

b = 18.7622 (4) Å

c = 11.7405 (3) Å

β = 92.634 (2)°

V = 1935.82 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 (2) K

0.54 × 0.52 × 0.48 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: none

14969 measured reflections

3804 independent reflections

2879 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.137

S = 1.06

3804 reflections

241 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 1997 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807061089/ln2004sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807061089/ln2004Isup2.hkl

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

C21H22N2O3	F000 = 744
Mr = 350.41	Dx = 1.202 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4673 reflections
a = 8.7974 (2) Å	θ = 2.6–26.8º
b = 18.7622 (4) Å	µ = 0.08 mm−1
c = 11.7405 (3) Å	T = 296 (2) K
β = 92.634 (2)º	Block, colourless
V = 1935.82 (8) Å3	0.54 × 0.52 × 0.48 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2879 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Monochromator: graphite	θmax = 26.0º
T = 296(2) K	θmin = 2.2º
phi and ω scans	h = −8→10
Absorption correction: none	k = −23→23
14969 measured reflections	l = −14→14
3804 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.043	w = 1/[σ2(Fo2) + (0.0654P)2 + 0.3695P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.137	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.23 e Å−3
3804 reflections	Δρmin = −0.21 e Å−3
241 parameters	Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.020 (2)
Secondary atom site location: difference Fourier map

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
C1	−0.1890 (3)	−0.01591 (13)	0.3028 (2)	0.0934 (7)
H1A	−0.2610	−0.0137	0.2389	0.140*
H1B	−0.2406	−0.0080	0.3720	0.140*
H1C	−0.1417	−0.0620	0.3055	0.140*
C2	−0.06900 (19)	0.04061 (9)	0.29032 (15)	0.0586 (4)
C3	−0.0157 (2)	0.08071 (10)	0.38294 (14)	0.0628 (5)
H3	−0.0547	0.0720	0.4539	0.075*
C4	0.0936 (2)	0.13334 (9)	0.37380 (13)	0.0563 (4)
C5	0.1455 (3)	0.17747 (12)	0.47572 (16)	0.0809 (6)
H5A	0.0757	0.1714	0.5354	0.121*
H5B	0.1487	0.2268	0.4543	0.121*
H5C	0.2452	0.1623	0.5022	0.121*
C6	0.15174 (18)	0.14558 (8)	0.26761 (13)	0.0484 (4)
H6	0.2263	0.1801	0.2594	0.058*
C7	0.09907 (16)	0.10652 (8)	0.17396 (12)	0.0438 (3)
C8	−0.01108 (17)	0.05444 (9)	0.18535 (14)	0.0509 (4)
H8	−0.0461	0.0287	0.1218	0.061*
C9	0.15521 (17)	0.11830 (8)	0.05858 (13)	0.0463 (4)
C10	0.33337 (17)	0.17600 (8)	−0.04896 (12)	0.0468 (4)
C11	0.26329 (16)	0.22905 (8)	−0.12040 (12)	0.0463 (4)
C12	0.14226 (19)	0.27236 (10)	−0.09065 (14)	0.0578 (4)
H12	0.1017	0.2681	−0.0192	0.069*
C13	0.0840 (2)	0.32105 (11)	−0.16753 (17)	0.0676 (5)
H13	0.0035	0.3500	−0.1478	0.081*
C14	0.1433 (2)	0.32802 (10)	−0.27457 (17)	0.0662 (5)
H14	0.1015	0.3610	−0.3262	0.079*
C15	0.26313 (19)	0.28648 (9)	−0.30426 (14)	0.0561 (4)
H15	0.3034	0.2916	−0.3757	0.067*
C16	0.32475 (16)	0.23645 (8)	−0.22752 (12)	0.0465 (4)
C17	0.45363 (18)	0.19228 (9)	−0.25804 (13)	0.0536 (4)
C18	0.65359 (19)	0.10239 (10)	−0.19097 (16)	0.0624 (5)
C19	0.6200 (3)	0.04906 (15)	−0.2852 (2)	0.1083 (9)
H19A	0.7114	0.0237	−0.3011	0.163*
H19B	0.5830	0.0736	−0.3526	0.163*
H19C	0.5443	0.0160	−0.2618	0.163*
C20	0.7848 (2)	0.15067 (13)	−0.2199 (3)	0.0987 (8)
H20A	0.8019	0.1851	−0.1602	0.148*
H20B	0.7603	0.1749	−0.2904	0.148*
H20C	0.8750	0.1226	−0.2275	0.148*
C21	0.6985 (3)	0.06425 (15)	−0.0799 (2)	0.1006 (8)
H21A	0.7924	0.0391	−0.0883	0.151*
H21B	0.6202	0.0310	−0.0619	0.151*
H21C	0.7112	0.0986	−0.0196	0.151*
N1	0.44872 (15)	0.13807 (7)	−0.07117 (11)	0.0521 (3)
N2	0.51350 (15)	0.14770 (7)	−0.17419 (11)	0.0531 (4)
O1	0.10477 (15)	0.09179 (7)	−0.02755 (9)	0.0687 (4)
O2	0.27700 (12)	0.16353 (6)	0.05844 (8)	0.0525 (3)
O3	0.50744 (16)	0.19522 (9)	−0.35226 (10)	0.0811 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0836 (15)	0.1065 (17)	0.0913 (15)	−0.0374 (13)	0.0168 (12)	0.0187 (13)
C2	0.0530 (9)	0.0635 (10)	0.0599 (10)	−0.0050 (8)	0.0100 (8)	0.0118 (8)
C3	0.0667 (11)	0.0748 (12)	0.0481 (9)	0.0025 (9)	0.0174 (8)	0.0133 (9)
C4	0.0660 (11)	0.0594 (10)	0.0438 (8)	0.0052 (8)	0.0057 (7)	0.0035 (7)
C5	0.1118 (17)	0.0858 (14)	0.0454 (10)	−0.0070 (12)	0.0064 (10)	−0.0040 (9)
C6	0.0504 (9)	0.0490 (8)	0.0461 (8)	−0.0003 (7)	0.0052 (6)	0.0036 (7)
C7	0.0421 (8)	0.0469 (8)	0.0428 (7)	0.0039 (6)	0.0067 (6)	0.0030 (6)
C8	0.0482 (9)	0.0533 (9)	0.0516 (9)	−0.0023 (7)	0.0051 (7)	0.0016 (7)
C9	0.0461 (8)	0.0484 (8)	0.0448 (8)	−0.0023 (6)	0.0054 (6)	−0.0002 (7)
C10	0.0441 (8)	0.0591 (9)	0.0379 (7)	−0.0071 (7)	0.0091 (6)	−0.0019 (7)
C11	0.0410 (8)	0.0560 (9)	0.0423 (8)	−0.0064 (6)	0.0072 (6)	−0.0055 (7)
C12	0.0516 (9)	0.0696 (11)	0.0533 (9)	0.0013 (8)	0.0153 (7)	−0.0044 (8)
C13	0.0540 (10)	0.0737 (12)	0.0757 (12)	0.0110 (9)	0.0101 (9)	−0.0027 (10)
C14	0.0611 (11)	0.0718 (11)	0.0650 (11)	0.0046 (9)	−0.0037 (9)	0.0100 (9)
C15	0.0551 (10)	0.0677 (10)	0.0459 (8)	−0.0044 (8)	0.0046 (7)	0.0018 (8)
C16	0.0420 (8)	0.0576 (9)	0.0401 (7)	−0.0058 (7)	0.0060 (6)	−0.0031 (7)
C17	0.0480 (9)	0.0685 (10)	0.0452 (8)	−0.0028 (8)	0.0126 (7)	−0.0021 (8)
C18	0.0509 (10)	0.0663 (11)	0.0710 (11)	0.0090 (8)	0.0148 (8)	−0.0055 (9)
C19	0.0810 (16)	0.1075 (18)	0.136 (2)	0.0210 (14)	0.0026 (15)	−0.0579 (17)
C20	0.0515 (12)	0.0989 (17)	0.148 (2)	0.0077 (11)	0.0250 (13)	0.0081 (16)
C21	0.0916 (17)	0.1129 (19)	0.0984 (17)	0.0488 (15)	0.0183 (13)	0.0172 (14)
N1	0.0488 (8)	0.0610 (8)	0.0472 (7)	−0.0021 (6)	0.0103 (6)	0.0013 (6)
N2	0.0481 (8)	0.0622 (8)	0.0501 (7)	0.0044 (6)	0.0150 (6)	0.0003 (6)
O1	0.0797 (9)	0.0804 (9)	0.0463 (6)	−0.0271 (7)	0.0065 (6)	−0.0067 (6)
O2	0.0512 (6)	0.0686 (7)	0.0383 (5)	−0.0120 (5)	0.0102 (4)	−0.0012 (5)
O3	0.0777 (9)	0.1161 (11)	0.0520 (7)	0.0211 (8)	0.0310 (6)	0.0112 (7)

C1—C2	1.508 (3)	C12—C13	1.367 (3)
C1—H1A	0.9600	C12—H12	0.9300
C1—H1B	0.9600	C13—C14	1.389 (3)
C1—H1C	0.9600	C13—H13	0.9300
C2—C8	1.380 (2)	C14—C15	1.369 (2)
C2—C3	1.386 (3)	C14—H14	0.9300
C3—C4	1.386 (2)	C15—C16	1.393 (2)
C3—H3	0.9300	C15—H15	0.9300
C4—C6	1.388 (2)	C16—C17	1.462 (2)
C4—C5	1.509 (3)	C17—O3	1.2243 (18)
C5—H5A	0.9600	C17—N2	1.378 (2)
C5—H5B	0.9600	C18—C19	1.511 (3)
C5—H5C	0.9600	C18—N2	1.517 (2)
C6—C7	1.383 (2)	C18—C20	1.518 (3)
C6—H6	0.9300	C18—C21	1.523 (3)
C7—C8	1.387 (2)	C19—H19A	0.9600
C7—C9	1.4796 (19)	C19—H19B	0.9600
C8—H8	0.9300	C19—H19C	0.9600
C9—O1	1.1939 (18)	C20—H20A	0.9600
C9—O2	1.3668 (18)	C20—H20B	0.9600
C10—N1	1.276 (2)	C20—H20C	0.9600
C10—O2	1.3958 (17)	C21—H21A	0.9600
C10—C11	1.424 (2)	C21—H21B	0.9600
C11—C16	1.3985 (19)	C21—H21C	0.9600
C11—C12	1.397 (2)	N1—N2	1.3725 (17)
C2—C1—H1A	109.5	C12—C13—H13	119.5
C2—C1—H1B	109.5	C14—C13—H13	119.5
H1A—C1—H1B	109.5	C15—C14—C13	120.16 (17)
C2—C1—H1C	109.5	C15—C14—H14	119.9
H1A—C1—H1C	109.5	C13—C14—H14	119.9
H1B—C1—H1C	109.5	C14—C15—C16	120.01 (15)
C8—C2—C3	118.23 (15)	C14—C15—H15	120.0
C8—C2—C1	120.53 (17)	C16—C15—H15	120.0
C3—C2—C1	121.24 (16)	C15—C16—C11	119.56 (14)
C2—C3—C4	122.48 (15)	C15—C16—C17	120.42 (14)
C2—C3—H3	118.8	C11—C16—C17	120.02 (14)
C4—C3—H3	118.8	O3—C17—N2	121.47 (15)
C3—C4—C6	118.23 (15)	O3—C17—C16	122.15 (16)
C3—C4—C5	121.03 (16)	N2—C17—C16	116.37 (13)
C6—C4—C5	120.73 (16)	C19—C18—N2	109.48 (15)
C4—C5—H5A	109.5	C19—C18—C20	110.88 (19)
C4—C5—H5B	109.5	N2—C18—C20	108.96 (15)
H5A—C5—H5B	109.5	C19—C18—C21	110.5 (2)
C4—C5—H5C	109.5	N2—C18—C21	109.42 (14)
H5A—C5—H5C	109.5	C20—C18—C21	107.58 (19)
H5B—C5—H5C	109.5	C18—C19—H19A	109.5
C7—C6—C4	120.15 (15)	C18—C19—H19B	109.5
C7—C6—H6	119.9	H19A—C19—H19B	109.5
C4—C6—H6	119.9	C18—C19—H19C	109.5
C6—C7—C8	120.43 (14)	H19A—C19—H19C	109.5
C6—C7—C9	122.33 (13)	H19B—C19—H19C	109.5
C8—C7—C9	117.24 (13)	C18—C20—H20A	109.5
C2—C8—C7	120.47 (15)	C18—C20—H20B	109.5
C2—C8—H8	119.8	H20A—C20—H20B	109.5
C7—C8—H8	119.8	C18—C20—H20C	109.5
O1—C9—O2	121.23 (13)	H20A—C20—H20C	109.5
O1—C9—C7	125.91 (14)	H20B—C20—H20C	109.5
O2—C9—C7	112.86 (12)	C18—C21—H21A	109.5
N1—C10—O2	114.20 (14)	C18—C21—H21B	109.5
N1—C10—C11	126.62 (13)	H21A—C21—H21B	109.5
O2—C10—C11	119.16 (13)	C18—C21—H21C	109.5
C16—C11—C12	119.86 (15)	H21A—C21—H21C	109.5
C16—C11—C10	115.11 (13)	H21B—C21—H21C	109.5
C12—C11—C10	125.03 (14)	C10—N1—N2	118.22 (13)
C13—C12—C11	119.38 (15)	N1—N2—C17	123.30 (13)
C13—C12—H12	120.3	N1—N2—C18	114.41 (13)
C11—C12—H12	120.3	C17—N2—C18	122.24 (13)
C12—C13—C14	121.03 (17)	C9—O2—C10	114.60 (11)
C8—C2—C3—C4	−0.5 (3)	C12—C11—C16—C15	−0.8 (2)
C1—C2—C3—C4	−179.50 (18)	C10—C11—C16—C15	179.37 (14)
C2—C3—C4—C6	−0.4 (3)	C12—C11—C16—C17	178.66 (14)
C2—C3—C4—C5	178.11 (18)	C10—C11—C16—C17	−1.1 (2)
C3—C4—C6—C7	0.9 (2)	C15—C16—C17—O3	−3.2 (3)
C5—C4—C6—C7	−177.60 (16)	C11—C16—C17—O3	177.35 (16)
C4—C6—C7—C8	−0.6 (2)	C15—C16—C17—N2	175.80 (14)
C4—C6—C7—C9	178.92 (14)	C11—C16—C17—N2	−3.7 (2)
C3—C2—C8—C7	0.9 (2)	O2—C10—N1—N2	−178.84 (12)
C1—C2—C8—C7	179.90 (17)	C11—C10—N1—N2	−0.7 (2)
C6—C7—C8—C2	−0.4 (2)	C10—N1—N2—C17	−5.0 (2)
C9—C7—C8—C2	−179.87 (14)	C10—N1—N2—C18	177.70 (14)
C6—C7—C9—O1	−172.15 (16)	O3—C17—N2—N1	−174.04 (16)
C8—C7—C9—O1	7.3 (2)	C16—C17—N2—N1	7.0 (2)
C6—C7—C9—O2	8.7 (2)	O3—C17—N2—C18	3.0 (3)
C8—C7—C9—O2	−171.80 (13)	C16—C17—N2—C18	−175.93 (14)
N1—C10—C11—C16	3.6 (2)	C19—C18—N2—N1	113.71 (19)
O2—C10—C11—C16	−178.33 (13)	C20—C18—N2—N1	−124.88 (18)
N1—C10—C11—C12	−176.22 (16)	C21—C18—N2—N1	−7.5 (2)
O2—C10—C11—C12	1.9 (2)	C19—C18—N2—C17	−63.6 (2)
C16—C11—C12—C13	0.8 (2)	C20—C18—N2—C17	57.8 (2)
C10—C11—C12—C13	−179.44 (16)	C21—C18—N2—C17	175.19 (18)
C11—C12—C13—C14	0.0 (3)	O1—C9—O2—C10	0.8 (2)
C12—C13—C14—C15	−0.8 (3)	C7—C9—O2—C10	179.99 (12)
C13—C14—C15—C16	0.8 (3)	N1—C10—O2—C9	−97.91 (16)
C14—C15—C16—C11	0.1 (2)	C11—C10—O2—C9	83.76 (17)
C14—C15—C16—C17	−179.44 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1i	0.93	2.56	3.391 (2)	149
C12—H12···O3ii	0.93	2.27	3.149 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1i	0.93	2.56	3.391 (2)	149
C12—H12⋯O3ii	0.93	2.27	3.149 (2)	157

Symmetry codes: (i) ; (ii) .