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The title compound, C38H32BrNO6, is a new photochromic tetra­hydro­azepinoiso­quinoline (THAI). The longest spiro bond [1.589 (4) Å] can be broken very easily by UV light, leading to ring opening. This explains the photochromic behaviour.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270104015860/sk1741sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270104015860/sk1741Isup2.hkl
Contains datablock I

CCDC reference: 251331

Comment top

Photochromism has been the subject of extensive investigation, due to its wide range of applications (Dürr, 1998). Tan et al. (2001) found a new photochromic system, the azaheptatriene tetrahydroazepinoisoquinoline (THAI), which constitutes a new class of molecules with interesting properties. In order to study the relationship between the substituting group and the structural and photophysical properties, we have synthesized several new THAI compounds using the method of Tan et al. (2001). The title compound, (I), is one of these and was investigated further with regard to its photochromic properties. The spectrum was also obtained (Feng, 2003). \sch

The molecular structure of (I) and the atom-labelling scheme are shown in Fig. 1. As can be seen from the figure, compound (I) can be divided into three parts, namely fluorene, dihydroazepine and isoquinoline. The molecule can also be thought of as consisting of seven rings, A, B (the plane through C1/C2/C5), C (the plane through C1/C7/C12/C13), D, E, F (atoms C21—C26) and G (atoms C27—C32) (Fig. 1). For clarity and completeness, please provide definitions of rings A, D and E.

Due to the rigid tetrahedral arrangement around the C4 spiro atom (Aldoshin, 1998), the fluorene part of the molecule of (I) is nonplanar, with a dihedral angle between rings F and G of 5.20 (19)°. The dihedral angle between rings E and F is 37.02 (13)°, and that between rings E and G is 42.21 (12)°.

From the bond angles, it follows that the seven-membered dihydroazepine ring exists in a slightly distorted boat shape. Taking plane E as the base Please check rephrasing, atom C4 deviates slightly from this plane, by −0.198 (6) Å. The dihedral angle between the plane passing through atoms C2, C3 and C5 and E is 32.2 (3), that between the plane through atoms C2, C4 and C5 and E is 9.1 (2), and that between the C6—N1 bond and E is 96.6°. The deviations of atoms N1, C3, C4 and C6 from plane B are 0.720 (5), 0.657 (6), −0.198 (6) and 0.564 (5) Å, respectively. While the C1—C2—C3 and C2—C1—N1 bond angles of 123.1 (3) and 119.3 (3)°, respectively, exhibit standard values, the N1—C6—C5 and C4—C5—C6 angles of 128.7 (3) and 127.5 (3)°, respectively, are distorted by about 8°. Atoms C2 and N1 are sp2-hybridized, since the sums of the bond angles around them are about 360° (Dorweiler et al., 1985), while the spiro-bonded atom C3, as well as atom C4, exhibit sp3 configurations, with bond angles of 108.5 (2)° for C5—C4—C3 and 108.8 (2)° for C4—C3—C2.

The dihydroisoquinoline region is also nonplanar, the plane passing through C1/C13/C14 being 22.0 (4)° below and that through C1/C13/N1 being 13.3 (3)° above plane C. The vertical distance between atom N1 and plane C is −0.279 (6) Å and that between atom C14 and plane C is 0.465 (6) Å.

The bond distances in (I), especially those in the azepine ring (Table 1), are of interest. The four bonds C2—C3, C3—C4, C4—C5, C1—N1 in the seven-membered ring are incorporated as single bonds, with bond lengths of 1.499 (4), 1.589 (4), 1.530 (4) and 1.433 (4) Å, respectively. Due to the tension in the region of the dihydroazepine ring, the C3—C4 bond [1.589 (4) Å], almost 0.05 Å greater than the corresponding normal bond length (1.540 Å), is the weakest and most elongated single bond in the azepine ring. This long C3—C4 bond makes it easily broken during the photochromic process of (I) (Dorweiler et al., 1988). The C5—C6 and C1—C2 bonds of 1.360 (4) and 1.320 (4) Å, respectively, have double-bond character, in agreement with the NMR data (Feng, 2003). The short N1—C6 bond of 1.369 (4) Å probably results from a partially delocalized imine/enamine structure.

Experimental top

The title compound, (I), was synthesized as described by Tan et al. (2001). Recrystallization from dichloromethane-ether solution (Ratio?) gave colourless prisms of (I) (m.p. 423–425 K).

Refinement top

The H atoms were added geometrically and treated as riding, with C—H distances in the range 0.93–0.98 Å, and with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for other H atoms. Please check added text.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SHELXTL (Sheldrick, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A view of the molecule of (I), with the atomic numbering scheme. Displacement ellipsoids are drawn at the 10% probability level and H atoms have been omitted for clarity.
Dimethyl 2-(4-bromophenyl)-10,11-dimethoxy-2,3,7,8-tetrahydrospiro[6- azacyclohepta[a]isoquinoline-3,9'-fluorene]-4,5-dicarboxylate top
Crystal data top
C38H32BrNO6F(000) = 2800
Mr = 678.56Dx = 1.437 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2541 reflections
a = 21.137 (4) Åθ = 2.4–21.9°
b = 9.1906 (16) ŵ = 1.36 mm1
c = 32.459 (6) ÅT = 298 K
β = 95.746 (3)°Prism, colourless
V = 6273.7 (19) Å30.45 × 0.30 × 0.05 mm
Z = 8
Data collection top
Bruker Smart APEX CCD area-detector
diffractometer
6150 independent reflections
Radiation source: fine-focus sealed tube3325 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.067
ϕ and ω scansθmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2426
Tmin = 0.580, Tmax = 0.935k = 1110
14103 measured reflectionsl = 3740
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H-atom parameters constrained
S = 0.83 w = 1/[σ2(Fo2) + (0.0292P)2]
where P = (Fo2 + 2Fc2)/3
6150 reflections(Δ/σ)max = 0.001
419 parametersΔρmax = 0.53 e Å3
0 restraintsΔρmin = 0.50 e Å3
Crystal data top
C38H32BrNO6V = 6273.7 (19) Å3
Mr = 678.56Z = 8
Monoclinic, C2/cMo Kα radiation
a = 21.137 (4) ŵ = 1.36 mm1
b = 9.1906 (16) ÅT = 298 K
c = 32.459 (6) Å0.45 × 0.30 × 0.05 mm
β = 95.746 (3)°
Data collection top
Bruker Smart APEX CCD area-detector
diffractometer
6150 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3325 reflections with I > 2σ(I)
Tmin = 0.580, Tmax = 0.935Rint = 0.067
14103 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.092H-atom parameters constrained
S = 0.83Δρmax = 0.53 e Å3
6150 reflectionsΔρmin = 0.50 e Å3
419 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
xyzUiso*/Ueq
Br10.320192 (17)0.60433 (4)1.004313 (12)0.06025 (15)
N10.64501 (11)0.1922 (3)0.89172 (8)0.0386 (7)
O10.64212 (10)0.7058 (3)0.77167 (7)0.0522 (6)
O20.75019 (10)0.6061 (2)0.75600 (7)0.0497 (6)
O30.46874 (10)0.0951 (2)0.84540 (7)0.0466 (6)
O40.54845 (10)0.2137 (3)0.88110 (8)0.0605 (7)
O50.65973 (10)0.1055 (3)0.93212 (8)0.0604 (7)
O60.68004 (11)0.1201 (3)0.86571 (8)0.0640 (7)
C10.62042 (14)0.3316 (3)0.87832 (10)0.0341 (8)
C20.56626 (13)0.3770 (3)0.89079 (9)0.0361 (8)
H20.55200.46990.88320.043*
C30.52659 (13)0.2859 (3)0.91659 (9)0.0322 (8)
H30.55570.24030.93820.039*
C40.49484 (13)0.1583 (3)0.88867 (9)0.0328 (8)
C50.54656 (14)0.0485 (3)0.88056 (9)0.0357 (8)
C60.61063 (15)0.0659 (3)0.88776 (10)0.0369 (8)
C70.65813 (13)0.4064 (3)0.84855 (9)0.0346 (8)
C80.63330 (14)0.5286 (3)0.82645 (10)0.0390 (8)
H80.59480.56770.83270.047*
C90.66452 (14)0.5917 (4)0.79584 (10)0.0379 (8)
C100.72274 (14)0.5354 (4)0.78671 (10)0.0376 (8)
C110.74743 (14)0.4174 (4)0.80807 (10)0.0422 (9)
H110.78620.37980.80190.051*
C120.71614 (14)0.3516 (3)0.83889 (10)0.0383 (8)
C130.74569 (14)0.2221 (4)0.86201 (10)0.0480 (9)
H13A0.74150.13690.84430.058*
H13B0.79070.24010.86920.058*
C140.71431 (13)0.1935 (4)0.90063 (10)0.0442 (9)
H14A0.72850.10050.91220.053*
H14B0.72660.26840.92090.053*
C150.47803 (13)0.3695 (3)0.93828 (10)0.0329 (8)
C160.43970 (14)0.4754 (4)0.91827 (10)0.0429 (9)
H160.44540.50020.89110.052*
C170.39311 (15)0.5448 (3)0.93795 (11)0.0445 (9)
H170.36800.61620.92420.053*
C180.38422 (14)0.5086 (4)0.97741 (11)0.0396 (8)
C190.42203 (14)0.4041 (4)0.99906 (10)0.0419 (8)
H190.41620.38011.02630.050*
C200.46835 (14)0.3377 (3)0.97866 (10)0.0390 (8)
H200.49420.26840.99280.047*
C210.45366 (14)0.2243 (3)0.85203 (10)0.0382 (8)
C220.47138 (17)0.2972 (4)0.81790 (11)0.0512 (10)
H220.51390.30190.81290.061*
C230.4251 (2)0.3632 (4)0.79132 (12)0.0734 (13)
H230.43620.41130.76790.088*
C240.3619 (2)0.3578 (5)0.79952 (14)0.0825 (14)
H240.33140.40800.78240.099*
C250.34352 (18)0.2809 (4)0.83207 (13)0.0651 (12)
H250.30080.27540.83660.078*
C260.38958 (15)0.2106 (4)0.85834 (10)0.0425 (9)
C270.38388 (14)0.1219 (4)0.89462 (10)0.0403 (8)
C280.33141 (15)0.0691 (4)0.91251 (13)0.0571 (11)
H280.29050.09080.90090.068*
C290.34042 (18)0.0152 (4)0.94749 (13)0.0629 (11)
H290.30530.04940.95970.075*
C300.40031 (18)0.0498 (4)0.96469 (12)0.0569 (11)
H300.40550.10580.98870.068*
C310.45354 (15)0.0018 (4)0.94663 (10)0.0433 (9)
H310.49420.02830.95760.052*
C320.44461 (14)0.0858 (3)0.91218 (10)0.0346 (8)
C330.58332 (15)0.7675 (4)0.77944 (12)0.0644 (12)
H33A0.55120.69320.77760.097*
H33B0.57170.84170.75930.097*
H33C0.58700.80940.80670.097*
C340.80846 (15)0.5486 (4)0.74473 (11)0.0650 (12)
H34A0.83970.55010.76830.097*
H34B0.82310.60670.72300.097*
H34C0.80200.45030.73520.097*
C350.52343 (15)0.1004 (4)0.87053 (10)0.0404 (8)
C360.43495 (16)0.2292 (4)0.83861 (12)0.0625 (11)
H36A0.46380.30390.83160.094*
H36B0.40190.21740.81630.094*
H36C0.41650.25630.86340.094*
C370.65310 (15)0.0670 (4)0.89251 (13)0.0466 (9)
C380.70090 (18)0.2282 (4)0.94238 (15)0.0980 (17)
H38A0.68290.31380.92890.147*
H38B0.70520.24270.97180.147*
H38C0.74190.20980.93320.147*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0548 (2)0.0645 (3)0.0660 (3)0.0144 (2)0.02862 (19)0.0024 (2)
N10.0294 (15)0.0370 (18)0.0494 (18)0.0019 (13)0.0042 (13)0.0055 (14)
O10.0480 (14)0.0471 (16)0.0647 (17)0.0088 (12)0.0212 (12)0.0184 (13)
O20.0430 (13)0.0558 (16)0.0536 (15)0.0004 (13)0.0207 (11)0.0071 (13)
O30.0462 (14)0.0362 (14)0.0569 (16)0.0048 (12)0.0032 (12)0.0031 (12)
O40.0499 (15)0.0364 (16)0.096 (2)0.0073 (13)0.0086 (14)0.0042 (15)
O50.0544 (15)0.0546 (17)0.0717 (19)0.0174 (14)0.0039 (14)0.0220 (15)
O60.0512 (15)0.0559 (18)0.089 (2)0.0108 (13)0.0283 (14)0.0164 (16)
C10.0315 (18)0.0292 (19)0.041 (2)0.0005 (15)0.0020 (15)0.0019 (16)
C20.0369 (18)0.029 (2)0.043 (2)0.0008 (16)0.0064 (15)0.0017 (16)
C30.0300 (17)0.0340 (19)0.0330 (19)0.0050 (15)0.0052 (14)0.0046 (15)
C40.0303 (17)0.0342 (19)0.0341 (19)0.0076 (15)0.0048 (15)0.0021 (15)
C50.037 (2)0.0298 (19)0.041 (2)0.0033 (16)0.0080 (16)0.0017 (15)
C60.037 (2)0.033 (2)0.042 (2)0.0080 (16)0.0108 (16)0.0021 (16)
C70.0298 (17)0.034 (2)0.040 (2)0.0007 (16)0.0049 (15)0.0015 (17)
C80.0295 (18)0.038 (2)0.051 (2)0.0023 (16)0.0109 (16)0.0007 (17)
C90.0362 (19)0.035 (2)0.044 (2)0.0041 (17)0.0085 (16)0.0006 (17)
C100.0352 (19)0.042 (2)0.038 (2)0.0052 (17)0.0123 (16)0.0025 (17)
C110.0257 (17)0.048 (2)0.054 (2)0.0020 (17)0.0106 (16)0.0010 (19)
C120.0315 (18)0.042 (2)0.042 (2)0.0011 (16)0.0050 (16)0.0000 (17)
C130.0310 (19)0.058 (3)0.055 (2)0.0079 (18)0.0058 (17)0.007 (2)
C140.0288 (19)0.048 (2)0.055 (2)0.0026 (17)0.0005 (16)0.0054 (19)
C150.0313 (17)0.030 (2)0.038 (2)0.0006 (15)0.0041 (15)0.0015 (16)
C160.044 (2)0.046 (2)0.040 (2)0.0066 (18)0.0123 (17)0.0050 (18)
C170.046 (2)0.037 (2)0.053 (2)0.0131 (17)0.0125 (18)0.0026 (18)
C180.0349 (19)0.039 (2)0.047 (2)0.0008 (17)0.0132 (17)0.0042 (18)
C190.045 (2)0.043 (2)0.038 (2)0.0045 (18)0.0110 (17)0.0004 (18)
C200.0373 (19)0.036 (2)0.044 (2)0.0027 (16)0.0039 (16)0.0063 (17)
C210.039 (2)0.036 (2)0.040 (2)0.0066 (16)0.0054 (16)0.0015 (17)
C220.058 (2)0.051 (2)0.044 (2)0.001 (2)0.001 (2)0.0050 (19)
C230.090 (3)0.074 (3)0.053 (3)0.004 (3)0.013 (3)0.021 (2)
C240.075 (3)0.083 (4)0.081 (4)0.013 (3)0.027 (3)0.026 (3)
C250.051 (2)0.072 (3)0.069 (3)0.010 (2)0.011 (2)0.000 (2)
C260.037 (2)0.043 (2)0.045 (2)0.0070 (17)0.0056 (17)0.0043 (18)
C270.036 (2)0.035 (2)0.050 (2)0.0001 (17)0.0042 (17)0.0109 (18)
C280.030 (2)0.062 (3)0.080 (3)0.0007 (19)0.008 (2)0.013 (2)
C290.050 (3)0.061 (3)0.082 (3)0.020 (2)0.030 (2)0.004 (3)
C300.065 (3)0.051 (3)0.057 (3)0.013 (2)0.018 (2)0.006 (2)
C310.040 (2)0.040 (2)0.052 (2)0.0010 (17)0.0128 (17)0.0021 (19)
C320.0329 (18)0.031 (2)0.040 (2)0.0022 (16)0.0057 (15)0.0017 (16)
C330.050 (2)0.069 (3)0.076 (3)0.016 (2)0.021 (2)0.028 (2)
C340.060 (3)0.075 (3)0.065 (3)0.004 (2)0.034 (2)0.010 (2)
C350.036 (2)0.039 (2)0.048 (2)0.0027 (18)0.0158 (17)0.0010 (19)
C360.051 (2)0.050 (3)0.087 (3)0.017 (2)0.011 (2)0.006 (2)
C370.036 (2)0.037 (2)0.067 (3)0.0022 (17)0.008 (2)0.000 (2)
C380.069 (3)0.064 (3)0.156 (5)0.029 (3)0.014 (3)0.044 (3)
Geometric parameters (Å, º) top
Br1—C181.899 (3)C15—C161.386 (4)
N1—C61.369 (4)C16—C171.382 (4)
N1—C11.433 (4)C16—H160.9300
N1—C141.464 (3)C17—C181.355 (4)
O1—C91.366 (4)C17—H170.9300
O1—C331.411 (3)C18—C191.394 (4)
O2—C101.367 (4)C19—C201.378 (4)
O2—C341.421 (3)C19—H190.9300
O3—C351.347 (4)C20—H200.9300
O3—C361.430 (4)C21—C221.378 (4)
O4—C351.202 (4)C21—C261.396 (4)
O5—C371.327 (4)C22—C231.378 (4)
O5—C381.443 (4)C22—H220.9300
O6—C371.191 (4)C23—C241.389 (5)
C1—C21.320 (4)C23—H230.9300
C1—C71.482 (4)C24—C251.360 (5)
C2—C31.499 (4)C24—H240.9300
C2—H20.9300C25—C261.388 (4)
C3—C151.511 (4)C25—H250.9300
C3—C41.589 (4)C26—C271.447 (4)
C3—H30.9800C27—C281.390 (4)
C4—C321.522 (4)C27—C321.392 (4)
C4—C211.527 (4)C28—C291.372 (5)
C4—C51.530 (4)C28—H280.9300
C5—C61.360 (4)C29—C301.369 (5)
C5—C351.478 (4)C29—H290.9300
C6—C371.514 (4)C30—C311.392 (4)
C7—C121.390 (4)C30—H300.9300
C7—C81.406 (4)C31—C321.375 (4)
C8—C91.375 (4)C31—H310.9300
C8—H80.9300C33—H33A0.9600
C9—C101.394 (4)C33—H33B0.9600
C10—C111.363 (4)C33—H33C0.9600
C11—C121.391 (4)C34—H34A0.9600
C11—H110.9300C34—H34B0.9600
C12—C131.508 (4)C34—H34C0.9600
C13—C141.499 (4)C36—H36A0.9600
C13—H13A0.9700C36—H36B0.9600
C13—H13B0.9700C36—H36C0.9600
C14—H14A0.9700C38—H38A0.9600
C14—H14B0.9700C38—H38B0.9600
C15—C201.378 (4)C38—H38C0.9600
C6—N1—C1123.8 (2)C20—C19—C18117.5 (3)
C6—N1—C14122.4 (3)C20—C19—H19121.2
C1—N1—C14112.2 (3)C18—C19—H19121.2
C9—O1—C33117.8 (3)C15—C20—C19122.9 (3)
C10—O2—C34116.9 (3)C15—C20—H20118.5
C35—O3—C36116.6 (3)C19—C20—H20118.5
C37—O5—C38115.8 (3)C22—C21—C26120.5 (3)
C2—C1—N1119.3 (3)C22—C21—C4129.7 (3)
C2—C1—C7126.4 (3)C26—C21—C4109.6 (3)
N1—C1—C7114.2 (3)C21—C22—C23118.9 (4)
C1—C2—C3123.1 (3)C21—C22—H22120.5
C1—C2—H2118.5C23—C22—H22120.5
C3—C2—H2118.5C22—C23—C24120.0 (4)
C2—C3—C15114.9 (3)C22—C23—H23120.0
C2—C3—C4108.8 (2)C24—C23—H23120.0
C15—C3—C4111.9 (2)C25—C24—C23121.5 (4)
C2—C3—H3107.0C25—C24—H24119.3
C15—C3—H3107.0C23—C24—H24119.3
C4—C3—H3107.0C24—C25—C26118.8 (4)
C32—C4—C21101.1 (2)C24—C25—H25120.6
C32—C4—C5110.1 (2)C26—C25—H25120.6
C21—C4—C5119.3 (3)C25—C26—C21120.0 (4)
C32—C4—C3108.3 (2)C25—C26—C27130.7 (3)
C21—C4—C3109.1 (2)C21—C26—C27109.4 (3)
C3—C4—C5108.5 (2)C28—C27—C32119.2 (3)
C6—C5—C35116.6 (3)C28—C27—C26132.2 (3)
C4—C5—C6127.5 (3)C32—C27—C26108.6 (3)
C35—C5—C4115.0 (3)C29—C28—C27119.5 (3)
C5—C6—N1128.7 (3)C29—C28—H28120.2
C5—C6—C37119.5 (3)C27—C28—H28120.2
N1—C6—C37111.8 (3)C30—C29—C28121.0 (3)
C12—C7—C8117.8 (3)C30—C29—H29119.5
C12—C7—C1121.6 (3)C28—C29—H29119.5
C8—C7—C1120.4 (3)C29—C30—C31120.5 (4)
C9—C8—C7121.6 (3)C29—C30—H30119.7
C9—C8—H8119.2C31—C30—H30119.7
C7—C8—H8119.2C32—C31—C30118.5 (3)
O1—C9—C8125.1 (3)C32—C31—H31120.8
O1—C9—C10115.2 (3)C30—C31—H31120.8
C8—C9—C10119.7 (3)C31—C32—C27121.2 (3)
C11—C10—O2125.5 (3)C31—C32—C4128.2 (3)
C11—C10—C9119.2 (3)C27—C32—C4110.5 (3)
O2—C10—C9115.3 (3)O1—C33—H33A109.5
C10—C11—C12121.8 (3)O1—C33—H33B109.5
C10—C11—H11119.1H33A—C33—H33B109.5
C12—C11—H11119.1O1—C33—H33C109.5
C7—C12—C11119.9 (3)H33A—C33—H33C109.5
C7—C12—C13120.3 (3)H33B—C33—H33C109.5
C11—C12—C13119.8 (3)O2—C34—H34A109.5
C14—C13—C12111.0 (3)O2—C34—H34B109.5
C14—C13—H13A109.4H34A—C34—H34B109.5
C12—C13—H13A109.4O2—C34—H34C109.5
C14—C13—H13B109.4H34A—C34—H34C109.5
C12—C13—H13B109.4H34B—C34—H34C109.5
H13A—C13—H13B108.0O4—C35—O3122.0 (3)
N1—C14—C13110.7 (3)O4—C35—C5127.8 (3)
N1—C14—H14A109.5O3—C35—C5110.2 (3)
C13—C14—H14A109.5O3—C36—H36A109.5
N1—C14—H14B109.5O3—C36—H36B109.5
C13—C14—H14B109.5H36A—C36—H36B109.5
H14A—C14—H14B108.1O3—C36—H36C109.5
C20—C15—C16117.3 (3)H36A—C36—H36C109.5
C20—C15—C3120.5 (3)H36B—C36—H36C109.5
C16—C15—C3122.1 (3)O6—C37—O5125.9 (3)
C17—C16—C15121.2 (3)O6—C37—C6125.3 (4)
C17—C16—H16119.4O5—C37—C6108.5 (3)
C15—C16—H16119.4O5—C38—H38A109.5
C18—C17—C16119.7 (3)O5—C38—H38B109.5
C18—C17—H17120.1H38A—C38—H38B109.5
C16—C17—H17120.1O5—C38—H38C109.5
C17—C18—C19121.3 (3)H38A—C38—H38C109.5
C17—C18—Br1119.6 (3)H38B—C38—H38C109.5
C19—C18—Br1119.1 (3)

Experimental details

Crystal data
Chemical formulaC38H32BrNO6
Mr678.56
Crystal system, space groupMonoclinic, C2/c
Temperature (K)298
a, b, c (Å)21.137 (4), 9.1906 (16), 32.459 (6)
β (°) 95.746 (3)
V3)6273.7 (19)
Z8
Radiation typeMo Kα
µ (mm1)1.36
Crystal size (mm)0.45 × 0.30 × 0.05
Data collection
DiffractometerBruker Smart APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.580, 0.935
No. of measured, independent and
observed [I > 2σ(I)] reflections
14103, 6150, 3325
Rint0.067
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.092, 0.83
No. of reflections6150
No. of parameters419
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.53, 0.50

Computer programs: SMART (Bruker, 2001), SMART, SHELXTL (Sheldrick, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL.

Selected geometric parameters (Å, º) top
Br1—C181.899 (3)C2—C31.499 (4)
N1—C61.369 (4)C3—C41.589 (4)
N1—C11.433 (4)C4—C51.530 (4)
C1—C21.320 (4)C5—C61.360 (4)
C2—C1—N1119.3 (3)C3—C4—C5108.5 (2)
C1—C2—C3123.1 (3)C4—C5—C6127.5 (3)
C2—C3—C4108.8 (2)C5—C6—N1128.7 (3)
 

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