rac-Diethyl 5-oxo-2-[(2,4,4-trimethyl-pentan-2-yl)amino]-4,5-dihydro-pyrano[3,2-c]chromene-3,4-dicarboxyl-ate.

The title compound, C(26)H(33)NO(7), comprises a racemic mixture of asymmetric mol-ecules containing one stereogenic centre. The dihedral angle between the mean planes of the fused pyran ring and the coumarin ring system is 8.12 (14)°. The mol-ecular structure features a short N-H⋯O contact, which generates an S(6) ring motif. The crystal packing are stabilized by C-H⋯O inter-actions.

Related literature

For a related structure, see: Inglebert et al. (2011 ▶). For general background and applications of coumarin derivatives, see: Griffiths et al. (1995 ▶); Yu et al. (2006 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C26H33NO7

M = 471.53

Orthorhombic,

a = 11.6910 (17) Å

b = 18.786 (3) Å

c = 11.7305 (15) Å

V = 2576.3 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.974, T max = 0.983

10574 measured reflections

3699 independent reflections

2668 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.148

S = 1.09

3699 reflections

314 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAIn class="Chemical">NT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811051786/rk2310sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051786/rk2310Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811051786/rk2310Isup3.cml

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

C26H33NO7	F(000) = 1008
Mr = 471.53	Dx = 1.216 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3699 reflections
a = 11.6910 (17) Å	θ = 2.1–24.7°
b = 18.786 (3) Å	µ = 0.09 mm−1
c = 11.7305 (15) Å	T = 295 K
V = 2576.3 (6) Å3	Block, colourless
Z = 4	0.30 × 0.25 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	3699 independent reflections
Radiation source: fine-focus sealed tube	2668 reflections with I > 2σ(I)
graphite	Rint = 0.040
ω and φ scans	θmax = 24.7°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→12
Tmin = 0.974, Tmax = 0.983	k = −22→21
10574 measured reflections	l = −13→8

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.078P)2 + 0.3187P] where P = (Fo2 + 2Fc2)/3
3699 reflections	(Δ/σ)max < 0.001
314 parameters	Δρmax = 0.31 e Å−3
1 restraint	Δρmin = −0.25 e Å−3

Geometry. All s.u.'s (except the s.u.'s in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.6377 (3)	−0.0116 (2)	0.3451 (3)	0.0508 (10)
C2	0.6418 (4)	0.0147 (3)	0.2347 (4)	0.0644 (12)
H2	0.6107	−0.0109	0.1743	0.077*
C3	0.6927 (4)	0.0791 (3)	0.2170 (4)	0.0755 (14)
H3	0.6946	0.0975	0.1435	0.091*
C4	0.7414 (4)	0.1179 (3)	0.3041 (4)	0.0683 (13)
H4	0.7766	0.1614	0.2894	0.082*
C5	0.7370 (3)	0.0910 (2)	0.4138 (3)	0.0541 (10)
H5	0.7691	0.1167	0.4736	0.065*
C6	0.6849 (3)	0.02601 (18)	0.4351 (3)	0.0423 (9)
C7	0.6755 (3)	−0.00743 (18)	0.5456 (3)	0.0394 (8)
C8	0.6263 (3)	−0.07045 (18)	0.5616 (3)	0.0395 (8)
C9	0.5766 (3)	−0.1081 (2)	0.4650 (4)	0.0538 (10)
C10	0.6226 (3)	−0.10563 (18)	0.6758 (3)	0.0427 (8)
H10	0.5457	−0.1252	0.6872	0.051*
C11	0.6445 (3)	−0.05068 (18)	0.7671 (3)	0.0385 (8)
C12	0.6961 (3)	0.01298 (17)	0.7433 (3)	0.0402 (8)
C13	0.7083 (4)	−0.1669 (2)	0.6807 (4)	0.0573 (10)
C14	0.9084 (5)	−0.1933 (3)	0.6863 (6)	0.108 (2)
H14A	0.9755	−0.1771	0.6450	0.129*
H14B	0.8860	−0.2391	0.6553	0.129*
C15	0.9368 (6)	−0.2013 (4)	0.8074 (7)	0.123 (2)
H15A	0.9581	−0.1559	0.8383	0.184*
H15B	0.9994	−0.2340	0.8155	0.184*
H15C	0.8714	−0.2192	0.8478	0.184*
C16	0.6163 (3)	−0.06638 (19)	0.8839 (3)	0.0493 (9)
C17	0.5375 (5)	−0.1526 (3)	1.0102 (4)	0.0780 (14)
H17A	0.5140	−0.1114	1.0541	0.094*
H17B	0.4738	−0.1857	1.0074	0.094*
C18	0.6319 (7)	−0.1854 (4)	1.0635 (7)	0.147 (3)
H18A	0.6500	−0.2289	1.0245	0.221*
H18B	0.6133	−0.1957	1.1415	0.221*
H18C	0.6966	−0.1540	1.0608	0.221*
C19	0.7794 (3)	0.13287 (19)	0.8039 (3)	0.0497 (9)
C20	0.6949 (3)	0.1798 (2)	0.7392 (5)	0.0683 (12)
H20A	0.6810	0.1598	0.6652	0.102*
H20B	0.7262	0.2268	0.7310	0.102*
H20C	0.6242	0.1824	0.7807	0.102*
C21	0.8934 (3)	0.13309 (19)	0.7391 (4)	0.0559 (10)
H21A	0.9180	0.1824	0.7360	0.067*
H21B	0.8756	0.1195	0.6614	0.067*
C22	0.7911 (5)	0.1623 (2)	0.9242 (4)	0.0801 (15)
H22A	0.7166	0.1721	0.9547	0.120*
H22B	0.8352	0.2054	0.9224	0.120*
H22C	0.8290	0.1279	0.9715	0.120*
C23	1.0000 (4)	0.0895 (3)	0.7732 (5)	0.0871 (16)
C24	1.0869 (5)	0.1021 (5)	0.6791 (9)	0.166 (3)
H24A	1.1541	0.0742	0.6936	0.249*
H24B	1.1070	0.1517	0.6770	0.249*
H24C	1.0545	0.0885	0.6071	0.249*
C25	1.0573 (6)	0.1221 (5)	0.8796 (8)	0.177 (4)
H25A	1.1344	0.1050	0.8856	0.266*
H25B	1.0152	0.1086	0.9465	0.266*
H25C	1.0579	0.1731	0.8730	0.266*
C26	0.9782 (6)	0.0111 (3)	0.7841 (11)	0.197 (5)
H26A	0.9416	−0.0060	0.7161	0.295*
H26B	0.9297	0.0024	0.8486	0.295*
H26C	1.0496	−0.0133	0.7944	0.295*
O1	0.5851 (3)	−0.07650 (15)	0.3600 (2)	0.0612 (7)
O2	0.5283 (3)	−0.16455 (17)	0.4702 (3)	0.0809 (9)
O3	0.7213 (2)	0.03244 (13)	0.6328 (2)	0.0469 (6)
O4	0.6857 (3)	−0.22770 (16)	0.6899 (4)	0.0995 (12)
O5	0.8155 (3)	−0.14240 (16)	0.6705 (3)	0.0857 (11)
O6	0.6299 (3)	−0.02675 (14)	0.9658 (2)	0.0674 (8)
O7	0.5678 (3)	−0.13089 (14)	0.8956 (2)	0.0648 (8)
N1	0.7291 (3)	0.06126 (16)	0.8183 (3)	0.0531 (8)
H1	0.7195	0.0488	0.8881	0.064*

	U11	U22	U33	U12	U13	U23
C1	0.047 (2)	0.065 (3)	0.041 (2)	0.0145 (19)	0.0032 (19)	0.0016 (19)
C2	0.061 (3)	0.097 (3)	0.035 (2)	0.022 (2)	0.000 (2)	0.005 (2)
C3	0.080 (3)	0.104 (4)	0.043 (3)	0.029 (3)	0.017 (2)	0.026 (3)
C4	0.069 (3)	0.079 (3)	0.057 (3)	0.013 (2)	0.019 (2)	0.029 (3)
C5	0.057 (2)	0.060 (2)	0.046 (3)	0.004 (2)	0.0088 (19)	0.0084 (19)
C6	0.0436 (19)	0.050 (2)	0.034 (2)	0.0126 (17)	0.0063 (16)	0.0075 (17)
C7	0.0359 (19)	0.0484 (19)	0.034 (2)	0.0050 (16)	0.0016 (16)	−0.0002 (17)
C8	0.0358 (19)	0.0450 (19)	0.038 (2)	0.0029 (16)	−0.0019 (16)	0.0002 (15)
C9	0.062 (3)	0.055 (2)	0.045 (2)	0.004 (2)	−0.012 (2)	−0.003 (2)
C10	0.044 (2)	0.045 (2)	0.038 (2)	−0.0045 (16)	−0.0007 (17)	0.0013 (15)
C11	0.0355 (18)	0.0477 (19)	0.032 (2)	−0.0039 (16)	0.0013 (15)	0.0071 (15)
C12	0.0406 (19)	0.0470 (19)	0.033 (2)	−0.0018 (16)	−0.0018 (18)	0.0036 (17)
C13	0.076 (3)	0.046 (2)	0.050 (2)	0.003 (2)	−0.001 (2)	0.0082 (18)
C14	0.097 (4)	0.095 (4)	0.131 (5)	0.052 (3)	0.024 (4)	0.031 (4)
C15	0.109 (5)	0.119 (5)	0.140 (6)	0.028 (4)	−0.011 (4)	0.025 (4)
C16	0.055 (2)	0.051 (2)	0.042 (2)	−0.0062 (18)	0.0017 (19)	0.0048 (18)
C17	0.092 (4)	0.078 (3)	0.063 (3)	−0.022 (3)	0.001 (3)	0.022 (2)
C18	0.143 (6)	0.158 (7)	0.140 (7)	0.025 (5)	−0.016 (5)	0.066 (6)
C19	0.053 (2)	0.047 (2)	0.049 (2)	−0.0072 (18)	0.0023 (19)	−0.0012 (17)
C20	0.059 (3)	0.058 (2)	0.088 (3)	0.001 (2)	0.007 (3)	0.004 (2)
C21	0.051 (2)	0.053 (2)	0.064 (3)	−0.0103 (17)	−0.010 (2)	0.0040 (19)
C22	0.100 (4)	0.075 (3)	0.065 (3)	−0.033 (3)	0.003 (3)	−0.015 (2)
C23	0.056 (3)	0.080 (3)	0.126 (5)	−0.003 (2)	−0.016 (3)	0.011 (3)
C24	0.068 (4)	0.217 (9)	0.214 (9)	0.036 (5)	0.029 (5)	0.018 (7)
C25	0.116 (6)	0.229 (9)	0.188 (9)	0.017 (6)	−0.090 (6)	−0.013 (8)
C26	0.086 (4)	0.079 (4)	0.425 (17)	0.010 (3)	−0.060 (7)	0.042 (7)
O1	0.0684 (18)	0.0741 (19)	0.0410 (17)	−0.0001 (15)	−0.0120 (14)	−0.0039 (14)
O2	0.103 (2)	0.0674 (18)	0.072 (2)	−0.0260 (18)	−0.026 (2)	−0.0017 (17)
O3	0.0557 (15)	0.0522 (14)	0.0328 (14)	−0.0126 (12)	0.0012 (12)	0.0036 (12)
O4	0.109 (3)	0.0437 (17)	0.145 (3)	0.0013 (18)	−0.018 (2)	0.0142 (18)
O5	0.065 (2)	0.0698 (18)	0.122 (3)	0.0217 (17)	0.0166 (19)	0.0305 (18)
O6	0.096 (2)	0.0688 (17)	0.0373 (17)	−0.0171 (16)	0.0010 (16)	0.0005 (14)
O7	0.0885 (19)	0.0589 (16)	0.0470 (17)	−0.0158 (15)	0.0058 (15)	0.0127 (13)
N1	0.067 (2)	0.0570 (19)	0.0351 (17)	−0.0181 (16)	−0.0014 (16)	−0.0014 (15)

C1—O1	1.377 (5)	C16—O7	1.345 (4)
C1—C6	1.385 (5)	C17—C18	1.409 (8)
C1—C2	1.386 (6)	C17—O7	1.449 (5)
C2—C3	1.364 (6)	C17—H17A	0.9700
C2—H2	0.9300	C17—H17B	0.9700
C3—C4	1.378 (7)	C18—H18A	0.9600
C3—H3	0.9300	C18—H18B	0.9600
C4—C5	1.383 (6)	C18—H18C	0.9600
C4—H4	0.9300	C19—N1	1.478 (5)
C5—C6	1.388 (5)	C19—C22	1.522 (6)
C5—H5	0.9300	C19—C20	1.526 (6)
C6—C7	1.445 (5)	C19—C21	1.535 (6)
C7—C8	1.329 (4)	C20—H20A	0.9600
C7—O3	1.376 (4)	C20—H20B	0.9600
C8—C9	1.457 (5)	C20—H20C	0.9600
C8—C10	1.494 (5)	C21—C23	1.543 (6)
C9—O2	1.203 (4)	C21—H21A	0.9700
C9—O1	1.372 (5)	C21—H21B	0.9700
C10—C11	1.509 (5)	C22—H22A	0.9600
C10—C13	1.528 (5)	C22—H22B	0.9600
C10—H10	0.9800	C22—H22C	0.9600
C11—C12	1.368 (5)	C23—C26	1.500 (8)
C11—C16	1.440 (5)	C23—C24	1.520 (10)
C12—N1	1.321 (5)	C23—C25	1.543 (10)
C12—O3	1.378 (4)	C24—H24A	0.9600
C13—O4	1.177 (4)	C24—H24B	0.9600
C13—O5	1.340 (5)	C24—H24C	0.9600
C14—O5	1.459 (5)	C25—H25A	0.9600
C14—C15	1.467 (9)	C25—H25B	0.9600
C14—H14A	0.9700	C25—H25C	0.9600
C14—H14B	0.9700	C26—H26A	0.9600
C15—H15A	0.9600	C26—H26B	0.9600
C15—H15B	0.9600	C26—H26C	0.9600
C15—H15C	0.9600	N1—H1	0.8600
C16—O6	1.226 (5)
O1—C1—C6	122.2 (3)	H17A—C17—H17B	108.2
O1—C1—C2	116.7 (4)	C17—C18—H18A	109.5
C6—C1—C2	121.1 (4)	C17—C18—H18B	109.5
C3—C2—C1	118.2 (4)	H18A—C18—H18B	109.5
C3—C2—H2	120.9	C17—C18—H18C	109.5
C1—C2—H2	120.9	H18A—C18—H18C	109.5
C2—C3—C4	122.5 (4)	H18B—C18—H18C	109.5
C2—C3—H3	118.8	N1—C19—C22	105.1 (3)
C4—C3—H3	118.8	N1—C19—C20	109.0 (3)
C3—C4—C5	118.7 (4)	C22—C19—C20	108.1 (4)
C3—C4—H4	120.6	N1—C19—C21	113.9 (3)
C5—C4—H4	120.6	C22—C19—C21	112.3 (4)
C4—C5—C6	120.4 (4)	C20—C19—C21	108.3 (3)
C4—C5—H5	119.8	C19—C20—H20A	109.5
C6—C5—H5	119.8	C19—C20—H20B	109.5
C1—C6—C5	119.1 (4)	H20A—C20—H20B	109.5
C1—C6—C7	115.6 (3)	C19—C20—H20C	109.5
C5—C6—C7	125.3 (3)	H20A—C20—H20C	109.5
C8—C7—O3	123.2 (3)	H20B—C20—H20C	109.5
C8—C7—C6	123.1 (3)	C19—C21—C23	124.8 (4)
O3—C7—C6	113.6 (3)	C19—C21—H21A	106.1
C7—C8—C9	119.7 (3)	C23—C21—H21A	106.1
C7—C8—C10	122.2 (3)	C19—C21—H21B	106.1
C9—C8—C10	118.1 (3)	C23—C21—H21B	106.1
O2—C9—O1	117.4 (4)	H21A—C21—H21B	106.3
O2—C9—C8	125.2 (4)	C19—C22—H22A	109.5
O1—C9—C8	117.4 (3)	C19—C22—H22B	109.5
C8—C10—C11	109.2 (3)	H22A—C22—H22B	109.5
C8—C10—C13	110.3 (3)	C19—C22—H22C	109.5
C11—C10—C13	112.2 (3)	H22A—C22—H22C	109.5
C8—C10—H10	108.3	H22B—C22—H22C	109.5
C11—C10—H10	108.3	C26—C23—C24	109.2 (7)
C13—C10—H10	108.3	C26—C23—C21	114.0 (4)
C12—C11—C16	118.3 (3)	C24—C23—C21	105.6 (5)
C12—C11—C10	121.9 (3)	C26—C23—C25	113.2 (7)
C16—C11—C10	119.8 (3)	C24—C23—C25	103.6 (6)
N1—C12—C11	126.4 (3)	C21—C23—C25	110.5 (5)
N1—C12—O3	112.4 (3)	C23—C24—H24A	109.5
C11—C12—O3	121.2 (3)	C23—C24—H24B	109.5
O4—C13—O5	123.5 (4)	H24A—C24—H24B	109.5
O4—C13—C10	126.0 (4)	C23—C24—H24C	109.5
O5—C13—C10	110.5 (3)	H24A—C24—H24C	109.5
O5—C14—C15	111.0 (5)	H24B—C24—H24C	109.5
O5—C14—H14A	109.4	C23—C25—H25A	109.5
C15—C14—H14A	109.4	C23—C25—H25B	109.5
O5—C14—H14B	109.4	H25A—C25—H25B	109.5
C15—C14—H14B	109.4	C23—C25—H25C	109.5
H14A—C14—H14B	108.0	H25A—C25—H25C	109.5
C14—C15—H15A	109.5	H25B—C25—H25C	109.5
C14—C15—H15B	109.5	C23—C26—H26A	109.5
H15A—C15—H15B	109.5	C23—C26—H26B	109.5
C14—C15—H15C	109.5	H26A—C26—H26B	109.5
H15A—C15—H15C	109.5	C23—C26—H26C	109.5
H15B—C15—H15C	109.5	H26A—C26—H26C	109.5
O6—C16—O7	121.4 (3)	H26B—C26—H26C	109.5
O6—C16—C11	126.3 (3)	C9—O1—C1	122.0 (3)
O7—C16—C11	112.2 (3)	C7—O3—C12	118.1 (2)
C18—C17—O7	110.1 (5)	C13—O5—C14	117.3 (4)
C18—C17—H17A	109.6	C16—O7—C17	116.9 (3)
O7—C17—H17A	109.6	C12—N1—C19	131.7 (3)
C18—C17—H17B	109.6	C12—N1—H1	114.2
O7—C17—H17B	109.6	C19—N1—H1	114.2
O1—C1—C2—C3	179.6 (3)	C10—C11—C12—O3	5.9 (5)
C6—C1—C2—C3	−0.6 (6)	C8—C10—C13—O4	−114.4 (5)
C1—C2—C3—C4	1.1 (6)	C11—C10—C13—O4	123.6 (5)
C2—C3—C4—C5	−1.0 (6)	C8—C10—C13—O5	64.3 (4)
C3—C4—C5—C6	0.3 (6)	C11—C10—C13—O5	−57.7 (4)
O1—C1—C6—C5	179.8 (3)	C12—C11—C16—O6	3.1 (6)
C2—C1—C6—C5	0.0 (5)	C10—C11—C16—O6	179.8 (4)
O1—C1—C6—C7	0.1 (5)	C12—C11—C16—O7	−179.0 (3)
C2—C1—C6—C7	−179.7 (3)	C10—C11—C16—O7	−2.3 (5)
C4—C5—C6—C1	0.1 (5)	N1—C19—C21—C23	−55.7 (5)
C4—C5—C6—C7	179.8 (3)	C22—C19—C21—C23	63.6 (5)
C1—C6—C7—C8	0.8 (5)	C20—C19—C21—C23	−177.1 (4)
C5—C6—C7—C8	−178.9 (3)	C19—C21—C23—C26	55.6 (8)
C1—C6—C7—O3	−178.7 (3)	C19—C21—C23—C24	175.4 (5)
C5—C6—C7—O3	1.7 (5)	C19—C21—C23—C25	−73.2 (6)
O3—C7—C8—C9	178.0 (3)	O2—C9—O1—C1	179.3 (3)
C6—C7—C8—C9	−1.4 (5)	C8—C9—O1—C1	−0.3 (5)
O3—C7—C8—C10	−3.7 (5)	C6—C1—O1—C9	−0.3 (5)
C6—C7—C8—C10	176.9 (3)	C2—C1—O1—C9	179.5 (4)
C7—C8—C9—O2	−178.4 (4)	C8—C7—O3—C12	−12.7 (4)
C10—C8—C9—O2	3.2 (6)	C6—C7—O3—C12	166.8 (3)
C7—C8—C9—O1	1.1 (5)	N1—C12—O3—C7	−169.8 (3)
C10—C8—C9—O1	−177.3 (3)	C11—C12—O3—C7	11.3 (4)
C7—C8—C10—C11	18.6 (4)	O4—C13—O5—C14	−7.9 (7)
C9—C8—C10—C11	−163.1 (3)	C10—C13—O5—C14	173.3 (4)
C7—C8—C10—C13	−105.2 (4)	C15—C14—O5—C13	−84.9 (6)
C9—C8—C10—C13	73.2 (4)	O6—C16—O7—C17	−2.9 (5)
C8—C10—C11—C12	−19.6 (4)	C11—C16—O7—C17	179.0 (4)
C13—C10—C11—C12	103.0 (4)	C18—C17—O7—C16	−86.8 (6)
C8—C10—C11—C16	163.8 (3)	C11—C12—N1—C19	−176.2 (3)
C13—C10—C11—C16	−73.6 (4)	O3—C12—N1—C19	4.9 (5)
C16—C11—C12—N1	3.8 (5)	C22—C19—N1—C12	176.9 (4)
C10—C11—C12—N1	−172.9 (3)	C20—C19—N1—C12	61.3 (5)
C16—C11—C12—O3	−177.4 (3)	C21—C19—N1—C12	−59.8 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6	0.86	1.99	2.659 (4)	135
C2—H2···O6i	0.93	2.47	3.252 (5)	141.
C4—H4···O4ii	0.93	2.43	3.306 (5)	157.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O6	0.86	1.99	2.659 (4)	135
C2—H2⋯O6i	0.93	2.47	3.252 (5)	141
C4—H4⋯O4ii	0.93	2.43	3.306 (5)	157

Symmetry codes: (i) ; (ii) .