1,4-Bis(8-tert-butyl-6-methyl-4H-1,3-benzoxazin-3-yl)benzene

The solid-state structure of the title compound, C₃₂H₄₀N₂O₂, is characterized by benzoxazine units with a cisoid geometry, and with the N atoms displaced from the planes of the heterocycles. The two benzoxazine groups are nearly coplanar.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.062
• wR factor = 0.160
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C33
PLAT480_ALERT_4_C Long H...A H-Bond Reported H23B   ..  CG1     ..       2.95 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1,4-Bis(8-tert-butyl-6-methyl-4H-1,3-benzoxazin-3-yl)benzene

Crystal data

C32H40N2O2	F(000) = 1048
Mr = 484.66	Dx = 1.134 Mg m^−3
Monoclinic, P21/c	Melting point = 424–426 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.267 (1) Å	Cell parameters from 5532 reflections
b = 15.443 (2) Å	θ = 2.3–24.6°
c = 17.913 (2) Å	µ = 0.07 mm^−1
β = 92.098 (2)°	T = 294 K
V = 2838.3 (6) Å^3	Block, colorless
Z = 4	0.25 × 0.23 × 0.12 mm

Data collection

Bruker SMART APEX CCD diffractometer	5180 independent reflections
Radiation source: fine-focus sealed tube	3379 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
Detector resolution: 0.661 pixels mm^-1	θmax = 25.4°, θmin = 1.7°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	k = −18→18
Tmin = 0.965, Tmax = 0.996	l = −21→21
21975 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.160	H-atom parameters not refined
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0696P)^2 + 0.5199P] where P = (Fo^2 + 2Fc^2)/3
5180 reflections	(Δ/σ)max < 0.001
333 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

Experimental. ¹H NMR (300 MHz, CDCl₃): δ 7.04 (s, 4H, phenylene CH), 6.89 (s, 2H, aromatic CH), 6.63 (s, 2H, aromatic CH), 5.25 (s, 4H, N–CH₂–O), 4.51 (s, 4H, N—CH₂—C), 2.22 (s, 6H, CH₃), 1.34 (s, 18H, C(CH₃)₃); FAB MS: m/z 484 (M⁺, 98%). IR (KBr, ν, cm^-1) 3421, 3040, 2998, 2958, 2910, 2863, 1742, 1608, 1571, 1513, 1476, 1445, 1387, 1362, 1322, 1252, 1222, 1176, 1133, 1098, 948, 939, 919, 856, 836, 750, 659, 610, 562, 522

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.6625 (2)	0.41329 (15)	−0.00776 (13)	0.0482 (6)
C2	0.6983 (3)	0.40315 (17)	−0.08103 (14)	0.0641 (7)
H2	0.6655	0.3565	−0.1087	0.077*
C3	0.7809 (3)	0.46027 (17)	−0.11361 (16)	0.0695 (8)
H3	0.8042	0.4509	−0.1626	0.083*
C4	0.8306 (2)	0.53166 (16)	−0.07542 (15)	0.0569 (7)
C5	0.7945 (2)	0.54223 (16)	−0.00240 (15)	0.0582 (7)
H5	0.8255	0.5896	0.0249	0.070*
C6	0.7126 (2)	0.48312 (16)	0.03095 (14)	0.0559 (6)
H6	0.6913	0.4911	0.0805	0.067*
O7	0.59445 (15)	0.37658 (10)	0.15518 (9)	0.0533 (4)
C8	0.5102 (2)	0.37703 (18)	0.08829 (14)	0.0617 (7)
H8A	0.4383	0.3375	0.0955	0.074*
H8B	0.4739	0.4346	0.0816	0.074*
N9	0.57328 (19)	0.35311 (14)	0.02219 (11)	0.0563 (6)
C10	0.6188 (3)	0.26361 (16)	0.02997 (13)	0.0614 (7)
H10A	0.6751	0.2499	−0.0107	0.074*
H10B	0.5445	0.2248	0.0267	0.074*
C11	0.7772 (2)	0.18056 (15)	0.11305 (14)	0.0556 (7)
H11	0.7858	0.1412	0.0742	0.067*
C12	0.8498 (2)	0.16847 (15)	0.17873 (14)	0.0546 (6)
C13	0.8349 (2)	0.22912 (15)	0.23478 (13)	0.0498 (6)
H13	0.8839	0.2220	0.2791	0.060*
C14	0.7519 (2)	0.29970 (14)	0.22915 (12)	0.0423 (5)
C15	0.6782 (2)	0.30746 (14)	0.16179 (12)	0.0423 (5)
C16	0.6922 (2)	0.24957 (14)	0.10343 (12)	0.0458 (6)
C17	0.9459 (3)	0.09546 (18)	0.18823 (18)	0.0839 (9)
H17A	0.9005	0.0412	0.1850	0.126*
H17B	0.9904	0.1002	0.2361	0.126*
H17C	1.0081	0.0985	0.1496	0.126*
C18	0.7437 (2)	0.36676 (15)	0.29172 (13)	0.0536 (6)
C19	0.7824 (3)	0.45603 (17)	0.26273 (17)	0.0738 (8)
H19A	0.8667	0.4526	0.2415	0.111*
H19B	0.7852	0.4967	0.3033	0.111*
H19C	0.7194	0.4748	0.2252	0.111*
C20	0.6057 (3)	0.37000 (19)	0.32141 (15)	0.0693 (8)
H20A	0.5449	0.3848	0.2815	0.104*
H20B	0.6021	0.4128	0.3601	0.104*
H20C	0.5836	0.3144	0.3413	0.104*
C21	0.8366 (3)	0.3447 (2)	0.35820 (16)	0.0861 (10)
H21A	0.8152	0.2886	0.3773	0.129*
H21B	0.8278	0.3873	0.3967	0.129*
H21C	0.9247	0.3444	0.3421	0.129*
O22	0.90470 (15)	0.72024 (11)	−0.03936 (10)	0.0609 (5)
C23	0.9857 (3)	0.65030 (18)	−0.0664 (2)	0.0763 (9)
H23A	1.0549	0.6752	−0.0950	0.092*
H23B	1.0260	0.6207	−0.0238	0.092*
N24	0.9178 (2)	0.58853 (14)	−0.11160 (14)	0.0693 (6)
C25	0.8657 (3)	0.63163 (18)	−0.17882 (16)	0.0772 (9)
H25A	0.8070	0.5926	−0.2059	0.093*
H25B	0.9367	0.6456	−0.2110	0.093*
C26	0.7030 (3)	0.74920 (18)	−0.21014 (14)	0.0643 (7)
H26	0.6908	0.7240	−0.2570	0.077*
C27	0.6306 (3)	0.82064 (17)	−0.19300 (14)	0.0602 (7)
C28	0.6500 (2)	0.85536 (15)	−0.12190 (13)	0.0522 (6)
H28	0.6000	0.9030	−0.1091	0.063*
C29	0.7394 (2)	0.82343 (14)	−0.06882 (12)	0.0438 (5)
C30	0.8132 (2)	0.75184 (15)	−0.09020 (13)	0.0478 (6)
C31	0.7940 (2)	0.71313 (16)	−0.15998 (14)	0.0554 (6)
C32	0.5316 (3)	0.8596 (2)	−0.24780 (17)	0.0910 (11)
H32A	0.5582	0.8494	−0.2979	0.137*
H32B	0.5256	0.9208	−0.2392	0.137*
H32C	0.4481	0.8334	−0.2411	0.137*
C33	0.7567 (2)	0.86609 (16)	0.00844 (13)	0.0532 (6)
C34	0.8933 (3)	0.9063 (2)	0.01510 (17)	0.0778 (9)
H34A	0.9006	0.9512	−0.0215	0.117*
H34B	0.9574	0.8624	0.0068	0.117*
H34C	0.9073	0.9303	0.0642	0.117*
C35	0.6578 (3)	0.93859 (19)	0.01977 (16)	0.0782 (8)
H35A	0.6700	0.9833	−0.0166	0.117*
H35B	0.6704	0.9622	0.0691	0.117*
H35C	0.5711	0.9157	0.0139	0.117*
C36	0.7376 (3)	0.7997 (2)	0.07079 (15)	0.0802 (9)
H36A	0.7455	0.8280	0.1184	0.120*
H36B	0.8028	0.7553	0.0681	0.120*
H36C	0.6527	0.7741	0.0648	0.120*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0420 (13)	0.0522 (14)	0.0501 (14)	−0.0046 (11)	−0.0042 (11)	0.0114 (11)
C2	0.0821 (19)	0.0564 (16)	0.0540 (16)	−0.0141 (14)	0.0050 (14)	0.0009 (13)
C3	0.092 (2)	0.0534 (16)	0.0651 (17)	−0.0041 (15)	0.0276 (15)	−0.0016 (14)
C4	0.0490 (14)	0.0491 (15)	0.0736 (18)	0.0031 (12)	0.0172 (13)	0.0083 (13)
C5	0.0610 (16)	0.0496 (15)	0.0637 (17)	−0.0079 (12)	−0.0029 (13)	0.0038 (12)
C6	0.0612 (16)	0.0581 (16)	0.0487 (14)	−0.0041 (13)	0.0042 (12)	0.0078 (12)
O7	0.0473 (9)	0.0562 (10)	0.0567 (10)	0.0077 (8)	0.0048 (8)	0.0060 (8)
C8	0.0382 (13)	0.0785 (19)	0.0683 (18)	−0.0026 (12)	0.0005 (13)	0.0222 (14)
N9	0.0493 (12)	0.0653 (14)	0.0539 (13)	−0.0118 (10)	−0.0053 (10)	0.0164 (10)
C10	0.0754 (17)	0.0581 (17)	0.0502 (15)	−0.0245 (14)	−0.0045 (13)	0.0040 (12)
C11	0.0749 (17)	0.0399 (13)	0.0530 (15)	−0.0076 (13)	0.0165 (13)	−0.0052 (11)
C12	0.0619 (16)	0.0443 (14)	0.0583 (16)	0.0074 (12)	0.0149 (13)	0.0043 (11)
C13	0.0504 (14)	0.0509 (14)	0.0480 (14)	−0.0002 (12)	0.0000 (11)	0.0062 (11)
C14	0.0399 (12)	0.0392 (12)	0.0484 (13)	−0.0070 (10)	0.0068 (10)	−0.0028 (10)
C15	0.0386 (12)	0.0407 (13)	0.0478 (13)	−0.0035 (10)	0.0041 (10)	0.0035 (10)
C16	0.0495 (13)	0.0410 (13)	0.0471 (13)	−0.0123 (11)	0.0027 (11)	0.0029 (11)
C17	0.103 (2)	0.0634 (18)	0.087 (2)	0.0324 (17)	0.0247 (18)	0.0126 (16)
C18	0.0487 (14)	0.0560 (15)	0.0561 (15)	−0.0072 (12)	0.0024 (12)	−0.0142 (12)
C19	0.0719 (18)	0.0556 (16)	0.095 (2)	−0.0125 (14)	0.0131 (16)	−0.0246 (15)
C20	0.0653 (17)	0.080 (2)	0.0631 (17)	−0.0041 (15)	0.0158 (14)	−0.0216 (14)
C21	0.081 (2)	0.110 (3)	0.0667 (19)	0.0034 (19)	−0.0178 (16)	−0.0319 (18)
O22	0.0475 (9)	0.0584 (11)	0.0764 (12)	−0.0012 (8)	−0.0060 (9)	0.0109 (9)
C23	0.0432 (15)	0.0606 (17)	0.126 (3)	0.0001 (14)	0.0186 (16)	0.0158 (18)
N24	0.0592 (13)	0.0526 (13)	0.0981 (18)	−0.0023 (11)	0.0302 (13)	0.0076 (13)
C25	0.100 (2)	0.0589 (18)	0.076 (2)	−0.0052 (16)	0.0450 (18)	0.0025 (15)
C26	0.088 (2)	0.0623 (18)	0.0424 (14)	−0.0272 (16)	0.0057 (14)	0.0047 (13)
C27	0.0695 (17)	0.0586 (17)	0.0517 (16)	−0.0256 (14)	−0.0094 (13)	0.0125 (13)
C28	0.0529 (14)	0.0476 (14)	0.0560 (15)	−0.0083 (11)	−0.0003 (12)	0.0088 (12)
C29	0.0405 (12)	0.0464 (13)	0.0446 (13)	−0.0121 (11)	0.0012 (10)	0.0070 (10)
C30	0.0416 (12)	0.0508 (14)	0.0512 (14)	−0.0096 (11)	0.0047 (11)	0.0113 (11)
C31	0.0649 (16)	0.0496 (15)	0.0529 (15)	−0.0158 (13)	0.0189 (13)	0.0012 (12)
C32	0.101 (2)	0.092 (2)	0.077 (2)	−0.0339 (19)	−0.0380 (19)	0.0272 (18)
C33	0.0548 (15)	0.0566 (15)	0.0481 (14)	−0.0082 (12)	−0.0002 (12)	0.0017 (12)
C34	0.0734 (19)	0.087 (2)	0.0719 (19)	−0.0232 (16)	−0.0123 (15)	−0.0134 (16)
C35	0.089 (2)	0.073 (2)	0.073 (2)	0.0014 (17)	0.0101 (16)	−0.0144 (15)
C36	0.098 (2)	0.091 (2)	0.0518 (16)	−0.0082 (18)	0.0090 (16)	0.0103 (15)

Geometric parameters (Å, º)

C1—C6	1.372 (3)	C20—H20A	0.9600
C1—C2	1.385 (3)	C20—H20B	0.9600
C1—N9	1.424 (3)	C20—H20C	0.9600
C2—C3	1.369 (3)	C21—H21A	0.9600
C2—H2	0.9300	C21—H21B	0.9600
C3—C4	1.385 (4)	C21—H21C	0.9600
C3—H3	0.9300	O22—C30	1.374 (3)
C4—C5	1.382 (3)	O22—C23	1.457 (3)
C4—N24	1.427 (3)	C23—N24	1.417 (4)
C5—C6	1.391 (3)	C23—H23A	0.9700
C5—H5	0.9300	C23—H23B	0.9700
C6—H6	0.9300	N24—C25	1.460 (4)
O7—C15	1.373 (3)	C25—C31	1.503 (4)
O7—C8	1.452 (3)	C25—H25A	0.9700
C8—N9	1.419 (3)	C25—H25B	0.9700
C8—H8A	0.9700	C26—C27	1.372 (4)
C8—H8B	0.9700	C26—C31	1.389 (3)
N9—C10	1.464 (3)	C26—H26	0.9300
C10—C16	1.508 (3)	C27—C28	1.389 (3)
C10—H10A	0.9700	C27—C32	1.512 (4)
C10—H10B	0.9700	C28—C29	1.388 (3)
C11—C12	1.382 (3)	C28—H28	0.9300
C11—C16	1.385 (3)	C29—C30	1.402 (3)
C11—H11	0.9300	C29—C33	1.537 (3)
C12—C13	1.386 (3)	C30—C31	1.393 (3)
C12—C17	1.504 (3)	C32—H32A	0.9600
C13—C14	1.385 (3)	C32—H32B	0.9600
C13—H13	0.9300	C32—H32C	0.9600
C14—C15	1.406 (3)	C33—C35	1.530 (4)
C14—C18	1.531 (3)	C33—C36	1.534 (3)
C15—C16	1.387 (3)	C33—C34	1.534 (3)
C17—H17A	0.9600	C34—H34A	0.9600
C17—H17B	0.9600	C34—H34B	0.9600
C17—H17C	0.9600	C34—H34C	0.9600
C18—C19	1.531 (4)	C35—H35A	0.9600
C18—C20	1.533 (3)	C35—H35B	0.9600
C18—C21	1.536 (4)	C35—H35C	0.9600
C19—H19A	0.9600	C36—H36A	0.9600
C19—H19B	0.9600	C36—H36B	0.9600
C19—H19C	0.9600	C36—H36C	0.9600
C6—C1—C2	117.4 (2)	C18—C20—H20C	109.5
C6—C1—N9	123.8 (2)	H20A—C20—H20C	109.5
C2—C1—N9	118.7 (2)	H20B—C20—H20C	109.5
C3—C2—C1	121.4 (2)	C18—C21—H21A	109.5
C3—C2—H2	119.3	C18—C21—H21B	109.5
C1—C2—H2	119.3	H21A—C21—H21B	109.5
C2—C3—C4	121.7 (2)	C18—C21—H21C	109.5
C2—C3—H3	119.2	H21A—C21—H21C	109.5
C4—C3—H3	119.2	H21B—C21—H21C	109.5
C5—C4—C3	117.0 (2)	C30—O22—C23	115.3 (2)
C5—C4—N24	123.5 (2)	N24—C23—O22	114.5 (2)
C3—C4—N24	119.5 (2)	N24—C23—H23A	108.6
C4—C5—C6	121.1 (2)	O22—C23—H23A	108.6
C4—C5—H5	119.5	N24—C23—H23B	108.6
C6—C5—H5	119.5	O22—C23—H23B	108.6
C1—C6—C5	121.3 (2)	H23A—C23—H23B	107.6
C1—C6—H6	119.3	C23—N24—C4	117.3 (2)
C5—C6—H6	119.3	C23—N24—C25	108.8 (2)
C15—O7—C8	115.29 (18)	C4—N24—C25	116.0 (2)
N9—C8—O7	114.25 (19)	N24—C25—C31	111.4 (2)
N9—C8—H8A	108.7	N24—C25—H25A	109.4
O7—C8—H8A	108.7	C31—C25—H25A	109.4
N9—C8—H8B	108.7	N24—C25—H25B	109.4
O7—C8—H8B	108.7	C31—C25—H25B	109.4
H8A—C8—H8B	107.6	H25A—C25—H25B	108.0
C8—N9—C1	117.7 (2)	C27—C26—C31	122.4 (2)
C8—N9—C10	108.66 (19)	C27—C26—H26	118.8
C1—N9—C10	116.4 (2)	C31—C26—H26	118.8
N9—C10—C16	111.5 (2)	C26—C27—C28	117.0 (2)
N9—C10—H10A	109.3	C26—C27—C32	122.2 (3)
C16—C10—H10A	109.3	C28—C27—C32	120.8 (3)
N9—C10—H10B	109.3	C29—C28—C27	124.1 (2)
C16—C10—H10B	109.3	C29—C28—H28	118.0
H10A—C10—H10B	108.0	C27—C28—H28	118.0
C12—C11—C16	121.9 (2)	C28—C29—C30	116.3 (2)
C12—C11—H11	119.1	C28—C29—C33	121.1 (2)
C16—C11—H11	119.1	C30—C29—C33	122.6 (2)
C11—C12—C13	117.1 (2)	O22—C30—C31	120.9 (2)
C11—C12—C17	121.9 (2)	O22—C30—C29	117.6 (2)
C13—C12—C17	120.9 (2)	C31—C30—C29	121.6 (2)
C14—C13—C12	124.3 (2)	C26—C31—C30	118.6 (2)
C14—C13—H13	117.9	C26—C31—C25	120.9 (2)
C12—C13—H13	117.9	C30—C31—C25	120.4 (2)
C13—C14—C15	116.1 (2)	C27—C32—H32A	109.5
C13—C14—C18	122.0 (2)	C27—C32—H32B	109.5
C15—C14—C18	121.9 (2)	H32A—C32—H32B	109.5
O7—C15—C16	121.2 (2)	C27—C32—H32C	109.5
O7—C15—C14	117.14 (19)	H32A—C32—H32C	109.5
C16—C15—C14	121.6 (2)	H32B—C32—H32C	109.5
C11—C16—C15	119.0 (2)	C35—C33—C36	106.9 (2)
C11—C16—C10	120.8 (2)	C35—C33—C34	107.6 (2)
C15—C16—C10	120.2 (2)	C36—C33—C34	110.7 (2)
C12—C17—H17A	109.5	C35—C33—C29	112.2 (2)
C12—C17—H17B	109.5	C36—C33—C29	110.8 (2)
H17A—C17—H17B	109.5	C34—C33—C29	108.6 (2)
C12—C17—H17C	109.5	C33—C34—H34A	109.5
H17A—C17—H17C	109.5	C33—C34—H34B	109.5
H17B—C17—H17C	109.5	H34A—C34—H34B	109.5
C14—C18—C19	109.8 (2)	C33—C34—H34C	109.5
C14—C18—C20	110.64 (19)	H34A—C34—H34C	109.5
C19—C18—C20	110.0 (2)	H34B—C34—H34C	109.5
C14—C18—C21	111.6 (2)	C33—C35—H35A	109.5
C19—C18—C21	107.6 (2)	C33—C35—H35B	109.5
C20—C18—C21	107.1 (2)	H35A—C35—H35B	109.5
C18—C19—H19A	109.5	C33—C35—H35C	109.5
C18—C19—H19B	109.5	H35A—C35—H35C	109.5
H19A—C19—H19B	109.5	H35B—C35—H35C	109.5
C18—C19—H19C	109.5	C33—C36—H36A	109.5
H19A—C19—H19C	109.5	C33—C36—H36B	109.5
H19B—C19—H19C	109.5	H36A—C36—H36B	109.5
C18—C20—H20A	109.5	C33—C36—H36C	109.5
C18—C20—H20B	109.5	H36A—C36—H36C	109.5
H20A—C20—H20B	109.5	H36B—C36—H36C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···Cg3^i	0.97	2.66	3.608 (3)	166
C8—H8B···Cg1^i	0.97	2.75	3.592 (3)	145
C23—H23A···Cg2^ii	0.97	2.68	3.650 (3)	174
C23—H23B···Cg1^ii	0.97	2.95	3.807 (3)	148
C32—H32C···Cg2^i	0.96	2.80	3.712 (3)	160

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