Ethyl 2-(4-carb-oxy-benzyl-idene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-thia-zolo[3,2-a]pyrimidine-6-carboxyl-ate-N,N-dimethyl-formamide (1/1).

In the title compound, C(24)H(20)N(2)O(5)S·C(3)H(7)NO, a benzene ring is positioned axially to the pyrimidine ring, which adopts a twist-boat conformation, and is inclined to its mean plane by 85.36 (7)°. In the crystal, inter-molecular C-H⋯O inter-actions result in centrosymmetric head-to-head dimers with an R(2) (2)(14) graph-set motif along the b axis. Pairs of C-H⋯O and O-H⋯O hydrogen bonds form centrosymmetric head-to-head dimers about inversion centres, corresponding to an R(2) (2)(7) graph-set motif along the a axis.

Related literature

For pharmacological properties of pyrimidine derivatives and general background, see: Alam et al. (2010 ▶). For a related structure, see: Jotani et al. (2010 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C24H20N2O5S·C3H7NO

M = 521.58

Triclinic,

a = 8.4146 (4) Å

b = 12.0699 (5) Å

c = 14.0185 (6) Å

α = 71.799 (2)°

β = 78.753 (2)°

γ = 86.488 (2)°

V = 1326.56 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.17 mm−1

T = 296 K

0.20 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEX CCD detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.967, T max = 0.975

23685 measured reflections

5788 independent reflections

3560 reflections with I > 2σ(I)’

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.178

S = 1.04

5788 reflections

339 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and CAMERON (Watkin et al., 1996 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812000050/pv2495sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000050/pv2495Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000050/pv2495Isup3.cml

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

C24H20N2O5S·C3H7NO	Z = 2
Mr = 521.58	F(000) = 548
Triclinic, P1	Dx = 1.306 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4146 (4) Å	Cell parameters from 5788 reflections
b = 12.0699 (5) Å	θ = 1.6–27.0°
c = 14.0185 (6) Å	µ = 0.17 mm−1
α = 71.799 (2)°	T = 296 K
β = 78.753 (2)°	Block, yellow
γ = 86.488 (2)°	0.20 × 0.20 × 0.15 mm
V = 1326.56 (10) Å3

Bruker SMART APEX CCD detector diffractometer	5788 independent reflections
Radiation source: fine-focus sealed tube	3560 reflections with I > 2σ(I)'
graphite	Rint = 0.033
ω scans	θmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −10→8
Tmin = 0.967, Tmax = 0.975	k = −15→14
23685 measured reflections	l = −17→17

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.103P)2] where P = (Fo2 + 2Fc2)/3
5788 reflections	(Δ/σ)max < 0.001
339 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Geometry. All s.u.'s (except the s.u. 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 > 2σ(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
N22	0.6187 (3)	0.93566 (19)	0.32137 (16)	0.0806 (6)
C81	0.4744 (4)	0.9872 (3)	0.3273 (2)	0.0860 (8)
H81	0.4495	1.0414	0.2685	0.103*
C82	0.7324 (4)	0.9640 (3)	0.2250 (2)	0.1124 (11)
H82A	0.6825	1.0170	0.1725	0.169*
H82B	0.7631	0.8939	0.2074	0.169*
H82C	0.8270	0.9997	0.2315	0.169*
C83	0.6722 (5)	0.8554 (3)	0.4099 (3)	0.1303 (14)
H83A	0.6222	0.8755	0.4699	0.195*
H83B	0.7878	0.8600	0.4014	0.195*
H83C	0.6420	0.7774	0.4170	0.195*
O11	0.3700 (2)	0.96682 (18)	0.40786 (15)	0.1004 (6)
S1	0.30622 (7)	0.34995 (5)	0.35943 (4)	0.0618 (2)
N1	0.1227 (2)	0.48407 (14)	0.24302 (12)	0.0505 (4)
N2	0.0013 (2)	0.40960 (16)	0.41686 (12)	0.0610 (5)
O1	−0.29300 (18)	0.64562 (14)	0.17146 (12)	0.0718 (5)
O2	−0.4299 (2)	0.5986 (2)	0.33005 (16)	0.1173 (8)
O3	0.27644 (19)	0.52114 (14)	0.08332 (11)	0.0702 (5)
O5	1.2299 (2)	0.16084 (16)	0.22813 (13)	0.0837 (5)
O4	1.0939 (2)	0.07417 (16)	0.38392 (13)	0.0839 (5)
H4	1.1835	0.0469	0.3928	0.126*
C1	0.5294 (3)	0.38515 (19)	0.17748 (16)	0.0588 (6)
H1	0.5440	0.4212	0.1073	0.071*
C2	0.3822 (3)	0.40097 (18)	0.22858 (15)	0.0538 (5)
C3	0.2609 (3)	0.47380 (18)	0.17423 (15)	0.0536 (5)
C4	0.1213 (3)	0.42052 (18)	0.34338 (15)	0.0527 (5)
C5	−0.0051 (2)	0.56909 (17)	0.21469 (15)	0.0514 (5)
H5	−0.0318	0.5646	0.1510	0.062*
C6	−0.1543 (3)	0.53676 (19)	0.29785 (16)	0.0562 (5)
C7	−0.1450 (3)	0.46191 (19)	0.39185 (15)	0.0579 (6)
C8	−0.2833 (3)	0.4227 (2)	0.47932 (17)	0.0775 (7)
H8A	−0.2833	0.4658	0.5264	0.116*
H8B	−0.2722	0.3410	0.5135	0.116*
H8C	−0.3834	0.4361	0.4543	0.116*
C9	−0.3069 (3)	0.5942 (2)	0.27206 (18)	0.0668 (6)
C10	−0.4341 (3)	0.7095 (2)	0.1380 (2)	0.0848 (8)
H10A	−0.4629	0.7697	0.1708	0.102*
H10B	−0.5257	0.6572	0.1556	0.102*
C11	−0.3925 (5)	0.7620 (4)	0.0270 (3)	0.1493 (17)
H11A	−0.2973	0.8093	0.0103	0.224*
H11B	−0.4809	0.8097	0.0030	0.224*
H11C	−0.3721	0.7015	−0.0049	0.224*
C12	0.6698 (3)	0.32199 (18)	0.21211 (15)	0.0565 (5)
C13	0.6715 (3)	0.2478 (2)	0.31156 (17)	0.0687 (6)
H13	0.5766	0.2368	0.3602	0.082*
C14	0.8092 (3)	0.1918 (2)	0.33831 (17)	0.0662 (6)
H14	0.8070	0.1426	0.4045	0.079*
C15	0.9529 (3)	0.20750 (18)	0.26740 (16)	0.0575 (5)
C16	0.9541 (3)	0.2815 (2)	0.16903 (16)	0.0626 (6)
H16	1.0498	0.2931	0.1210	0.075*
C17	0.8164 (3)	0.3372 (2)	0.14224 (16)	0.0631 (6)
H17	0.8198	0.3865	0.0760	0.076*
C18	1.1052 (3)	0.1454 (2)	0.29103 (18)	0.0642 (6)
C19	0.0875 (3)	0.7233 (2)	0.2777 (2)	0.0732 (7)
H19	0.0673	0.6714	0.3436	0.088*
C20	0.1494 (4)	0.8341 (2)	0.2594 (3)	0.0925 (9)
H20	0.1719	0.8557	0.3136	0.111*
C21	0.1769 (3)	0.9101 (3)	0.1647 (3)	0.0941 (9)
H21	0.2184	0.9836	0.1536	0.113*
C22	0.1446 (4)	0.8801 (2)	0.0860 (3)	0.0948 (9)
H22	0.1636	0.9335	0.0207	0.114*
C23	0.0835 (3)	0.7708 (2)	0.10042 (18)	0.0736 (7)
H123	0.0609	0.7513	0.0453	0.088*
C24	0.0565 (2)	0.69169 (18)	0.19627 (16)	0.0563 (5)

	U11	U22	U33	U12	U13	U23
N22	0.0713 (15)	0.0885 (15)	0.0760 (14)	0.0075 (11)	−0.0098 (11)	−0.0205 (12)
C81	0.0765 (19)	0.099 (2)	0.0758 (18)	0.0023 (16)	−0.0131 (15)	−0.0185 (15)
C82	0.096 (2)	0.136 (3)	0.093 (2)	−0.003 (2)	0.0108 (18)	−0.035 (2)
C83	0.138 (3)	0.138 (3)	0.092 (2)	0.052 (2)	−0.030 (2)	−0.007 (2)
O11	0.0815 (14)	0.1229 (17)	0.0802 (13)	0.0172 (11)	−0.0075 (11)	−0.0152 (11)
S1	0.0619 (4)	0.0721 (4)	0.0442 (3)	0.0072 (3)	−0.0036 (2)	−0.0126 (3)
N1	0.0504 (10)	0.0541 (10)	0.0437 (9)	0.0008 (8)	−0.0037 (7)	−0.0136 (7)
N2	0.0576 (12)	0.0769 (13)	0.0442 (10)	−0.0033 (9)	0.0006 (8)	−0.0182 (9)
O1	0.0460 (9)	0.0916 (12)	0.0690 (10)	0.0024 (8)	−0.0089 (7)	−0.0137 (8)
O2	0.0598 (12)	0.172 (2)	0.0863 (13)	0.0252 (12)	0.0123 (10)	−0.0116 (13)
O3	0.0627 (10)	0.0922 (12)	0.0420 (8)	0.0120 (8)	0.0000 (7)	−0.0091 (8)
O5	0.0639 (11)	0.1041 (14)	0.0731 (11)	0.0089 (9)	−0.0061 (9)	−0.0185 (9)
O4	0.0758 (12)	0.0851 (12)	0.0725 (11)	0.0157 (10)	−0.0111 (9)	−0.0025 (9)
C1	0.0627 (14)	0.0618 (13)	0.0480 (11)	0.0066 (10)	−0.0040 (10)	−0.0163 (10)
C2	0.0579 (13)	0.0552 (12)	0.0446 (11)	0.0009 (10)	−0.0025 (9)	−0.0144 (9)
C3	0.0528 (12)	0.0596 (13)	0.0449 (11)	0.0011 (9)	−0.0006 (9)	−0.0167 (10)
C4	0.0566 (13)	0.0578 (13)	0.0428 (11)	−0.0036 (10)	−0.0052 (9)	−0.0162 (9)
C5	0.0454 (11)	0.0616 (13)	0.0460 (10)	−0.0023 (9)	−0.0043 (9)	−0.0170 (9)
C6	0.0476 (12)	0.0684 (14)	0.0536 (12)	−0.0072 (10)	−0.0014 (9)	−0.0234 (11)
C7	0.0493 (13)	0.0750 (15)	0.0512 (12)	−0.0068 (10)	−0.0005 (9)	−0.0260 (11)
C8	0.0581 (15)	0.111 (2)	0.0544 (13)	−0.0087 (13)	0.0049 (11)	−0.0200 (13)
C9	0.0487 (13)	0.0808 (16)	0.0644 (14)	−0.0059 (11)	−0.0017 (11)	−0.0171 (12)
C10	0.0514 (15)	0.0922 (19)	0.099 (2)	0.0032 (13)	−0.0153 (13)	−0.0124 (16)
C11	0.096 (3)	0.213 (4)	0.095 (2)	0.045 (3)	−0.021 (2)	0.009 (3)
C12	0.0574 (13)	0.0597 (13)	0.0496 (11)	0.0056 (10)	−0.0006 (10)	−0.0197 (10)
C13	0.0628 (15)	0.0707 (15)	0.0581 (13)	0.0114 (11)	0.0076 (11)	−0.0127 (11)
C14	0.0710 (16)	0.0635 (14)	0.0541 (13)	0.0105 (11)	−0.0035 (11)	−0.0111 (11)
C15	0.0604 (14)	0.0545 (13)	0.0604 (13)	0.0045 (10)	−0.0100 (10)	−0.0232 (10)
C16	0.0619 (14)	0.0734 (15)	0.0491 (12)	0.0004 (11)	0.0002 (10)	−0.0205 (11)
C17	0.0643 (15)	0.0748 (15)	0.0456 (11)	0.0054 (11)	−0.0046 (10)	−0.0161 (10)
C18	0.0657 (16)	0.0651 (15)	0.0643 (14)	0.0028 (11)	−0.0126 (12)	−0.0238 (12)
C19	0.0745 (17)	0.0701 (16)	0.0810 (17)	−0.0003 (12)	−0.0282 (13)	−0.0235 (13)
C20	0.094 (2)	0.0787 (19)	0.121 (3)	−0.0065 (16)	−0.0330 (19)	−0.0448 (19)
C21	0.079 (2)	0.0646 (18)	0.132 (3)	−0.0110 (14)	0.0014 (18)	−0.0317 (19)
C22	0.101 (2)	0.0659 (18)	0.091 (2)	−0.0015 (15)	0.0207 (17)	−0.0094 (15)
C23	0.0810 (17)	0.0666 (16)	0.0605 (14)	−0.0029 (13)	0.0094 (12)	−0.0148 (12)
C24	0.0385 (11)	0.0596 (13)	0.0665 (13)	0.0034 (9)	−0.0004 (9)	−0.0197 (11)

N22—C81	1.330 (3)	C6—C9	1.475 (3)
N22—C83	1.447 (3)	C7—C8	1.493 (3)
N22—C82	1.450 (3)	C8—H8A	0.9600
C81—O11	1.254 (3)	C8—H8B	0.9600
C81—H81	0.9300	C8—H8C	0.9600
C82—H82A	0.9600	C10—C11	1.463 (4)
C82—H82B	0.9600	C10—H10A	0.9700
C82—H82C	0.9600	C10—H10B	0.9700
C83—H83A	0.9600	C11—H11A	0.9600
C83—H83B	0.9600	C11—H11B	0.9600
C83—H83C	0.9600	C11—H11C	0.9600
S1—C2	1.743 (2)	C12—C17	1.399 (3)
S1—C4	1.747 (2)	C12—C13	1.404 (3)
N1—C4	1.374 (2)	C13—C14	1.363 (3)
N1—C3	1.384 (2)	C13—H13	0.9300
N1—C5	1.464 (3)	C14—C15	1.388 (3)
N2—C4	1.274 (3)	C14—H14	0.9300
N2—C7	1.404 (3)	C15—C16	1.388 (3)
O1—C9	1.336 (3)	C15—C18	1.486 (3)
O1—C10	1.451 (3)	C16—C17	1.362 (3)
O2—C9	1.194 (3)	C16—H16	0.9300
O3—C3	1.207 (2)	C17—H17	0.9300
O5—C18	1.214 (3)	C19—C24	1.384 (3)
O4—C18	1.306 (3)	C19—C20	1.395 (3)
O4—H4	0.8200	C19—H19	0.9300
C1—C2	1.339 (3)	C20—C21	1.343 (4)
C1—C12	1.447 (3)	C20—H20	0.9300
C1—H1	0.9300	C21—C22	1.342 (4)
C2—C3	1.473 (3)	C21—H21	0.9300
C5—C6	1.514 (3)	C22—C23	1.387 (4)
C5—C24	1.526 (3)	C22—H22	0.9300
C5—H5	0.9800	C23—C24	1.369 (3)
C6—C7	1.359 (3)	C23—H123	0.9300
C81—N22—C83	122.3 (3)	O2—C9—O1	121.6 (2)
C81—N22—C82	120.1 (2)	O2—C9—C6	127.1 (2)
C83—N22—C82	117.5 (3)	O1—C9—C6	111.30 (19)
O11—C81—N22	123.6 (3)	O1—C10—C11	107.4 (2)
O11—C81—H81	118.2	O1—C10—H10A	110.2
N22—C81—H81	118.2	C11—C10—H10A	110.2
N22—C82—H82A	109.5	O1—C10—H10B	110.2
N22—C82—H82B	109.5	C11—C10—H10B	110.2
H82A—C82—H82B	109.5	H10A—C10—H10B	108.5
N22—C82—H82C	109.5	C10—C11—H11A	109.5
H82A—C82—H82C	109.5	C10—C11—H11B	109.5
H82B—C82—H82C	109.5	H11A—C11—H11B	109.5
N22—C83—H83A	109.5	C10—C11—H11C	109.5
N22—C83—H83B	109.5	H11A—C11—H11C	109.5
H83A—C83—H83B	109.5	H11B—C11—H11C	109.5
N22—C83—H83C	109.5	C17—C12—C13	117.0 (2)
H83A—C83—H83C	109.5	C17—C12—C1	117.96 (19)
H83B—C83—H83C	109.5	C13—C12—C1	125.00 (19)
C2—S1—C4	91.62 (10)	C14—C13—C12	121.4 (2)
C4—N1—C3	115.96 (18)	C14—C13—H13	119.3
C4—N1—C5	120.81 (16)	C12—C13—H13	119.3
C3—N1—C5	122.69 (16)	C13—C14—C15	120.5 (2)
C4—N2—C7	116.87 (17)	C13—C14—H14	119.8
C9—O1—C10	115.94 (19)	C15—C14—H14	119.8
C18—O4—H4	109.5	C16—C15—C14	119.0 (2)
C2—C1—C12	131.4 (2)	C16—C15—C18	118.1 (2)
C2—C1—H1	114.3	C14—C15—C18	122.9 (2)
C12—C1—H1	114.3	C17—C16—C15	120.5 (2)
C1—C2—C3	120.46 (19)	C17—C16—H16	119.7
C1—C2—S1	128.94 (18)	C15—C16—H16	119.7
C3—C2—S1	110.56 (14)	C16—C17—C12	121.5 (2)
O3—C3—N1	123.1 (2)	C16—C17—H17	119.2
O3—C3—C2	126.56 (19)	C12—C17—H17	119.2
N1—C3—C2	110.27 (17)	O5—C18—O4	123.2 (2)
N2—C4—N1	125.9 (2)	O5—C18—C15	121.9 (2)
N2—C4—S1	122.68 (16)	O4—C18—C15	114.9 (2)
N1—C4—S1	111.41 (15)	C24—C19—C20	119.0 (3)
N1—C5—C6	108.64 (16)	C24—C19—H19	120.5
N1—C5—C24	109.51 (16)	C20—C19—H19	120.5
C6—C5—C24	113.05 (16)	C21—C20—C19	120.8 (3)
N1—C5—H5	108.5	C21—C20—H20	119.6
C6—C5—H5	108.5	C19—C20—H20	119.6
C24—C5—H5	108.5	C22—C21—C20	120.2 (3)
C7—C6—C9	122.49 (19)	C22—C21—H21	119.9
C7—C6—C5	121.1 (2)	C20—C21—H21	119.9
C9—C6—C5	116.33 (19)	C21—C22—C23	121.0 (3)
C6—C7—N2	122.32 (18)	C21—C22—H22	119.5
C6—C7—C8	126.0 (2)	C23—C22—H22	119.5
N2—C7—C8	111.64 (19)	C24—C23—C22	119.6 (3)
C7—C8—H8A	109.5	C24—C23—H123	120.2
C7—C8—H8B	109.5	C22—C23—H123	120.2
H8A—C8—H8B	109.5	C23—C24—C19	119.3 (2)
C7—C8—H8C	109.5	C23—C24—C5	121.2 (2)
H8A—C8—H8C	109.5	C19—C24—C5	119.48 (19)
H8B—C8—H8C	109.5
C83—N22—C81—O11	−3.7 (5)	C10—O1—C9—O2	1.9 (4)
C82—N22—C81—O11	179.8 (3)	C10—O1—C9—C6	−177.28 (19)
C12—C1—C2—C3	177.9 (2)	C7—C6—C9—O2	12.6 (4)
C12—C1—C2—S1	0.5 (4)	C5—C6—C9—O2	−165.1 (3)
C4—S1—C2—C1	178.1 (2)	C7—C6—C9—O1	−168.28 (19)
C4—S1—C2—C3	0.47 (15)	C5—C6—C9—O1	14.0 (3)
C4—N1—C3—O3	177.18 (19)	C9—O1—C10—C11	178.0 (3)
C5—N1—C3—O3	−11.1 (3)	C2—C1—C12—C17	−169.5 (2)
C4—N1—C3—C2	−4.2 (2)	C2—C1—C12—C13	9.1 (4)
C5—N1—C3—C2	167.44 (16)	C17—C12—C13—C14	−1.0 (4)
C1—C2—C3—O3	2.6 (3)	C1—C12—C13—C14	−179.7 (2)
S1—C2—C3—O3	−179.55 (19)	C12—C13—C14—C15	0.5 (4)
C1—C2—C3—N1	−175.93 (19)	C13—C14—C15—C16	0.2 (4)
S1—C2—C3—N1	1.9 (2)	C13—C14—C15—C18	−177.7 (2)
C7—N2—C4—N1	3.8 (3)	C14—C15—C16—C17	−0.4 (3)
C7—N2—C4—S1	−174.05 (14)	C18—C15—C16—C17	177.6 (2)
C3—N1—C4—N2	−173.4 (2)	C15—C16—C17—C12	−0.1 (4)
C5—N1—C4—N2	14.7 (3)	C13—C12—C17—C16	0.8 (3)
C3—N1—C4—S1	4.6 (2)	C1—C12—C17—C16	179.59 (19)
C5—N1—C4—S1	−167.20 (14)	C16—C15—C18—O5	2.5 (3)
C2—S1—C4—N2	175.35 (19)	C14—C15—C18—O5	−179.6 (2)
C2—S1—C4—N1	−2.79 (15)	C16—C15—C18—O4	−177.68 (19)
C4—N1—C5—C6	−23.1 (2)	C14—C15—C18—O4	0.2 (3)
C3—N1—C5—C6	165.58 (17)	C24—C19—C20—C21	0.9 (4)
C4—N1—C5—C24	100.8 (2)	C19—C20—C21—C22	0.1 (5)
C3—N1—C5—C24	−70.5 (2)	C20—C21—C22—C23	−0.3 (5)
N1—C5—C6—C7	16.6 (3)	C21—C22—C23—C24	−0.5 (4)
C24—C5—C6—C7	−105.2 (2)	C22—C23—C24—C19	1.5 (4)
N1—C5—C6—C9	−165.65 (17)	C22—C23—C24—C5	−177.9 (2)
C24—C5—C6—C9	72.6 (2)	C20—C19—C24—C23	−1.6 (4)
C9—C6—C7—N2	−178.39 (19)	C20—C19—C24—C5	177.7 (2)
C5—C6—C7—N2	−0.8 (3)	N1—C5—C24—C23	111.4 (2)
C9—C6—C7—C8	3.0 (4)	C6—C5—C24—C23	−127.4 (2)
C5—C6—C7—C8	−179.4 (2)	N1—C5—C24—C19	−67.9 (2)
C4—N2—C7—C6	−10.7 (3)	C6—C5—C24—C19	53.3 (3)
C4—N2—C7—C8	168.12 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C81—H81···O5i	0.93	2.32	3.053 (3)	135
O4—H4···O11ii	0.82	1.81	2.618 (3)	170
C17—H17···O3iii	0.93	2.43	3.310 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C81—H81⋯O5i	0.93	2.32	3.053 (3)	135
O4—H4⋯O11ii	0.82	1.81	2.618 (3)	170
C17—H17⋯O3iii	0.93	2.43	3.310 (3)	157

Symmetry codes: (i) ; (ii) ; (iii) .