N-(5-Benzoyl-2-oxo-4-phenyl-1,2-di­hydro­pyrimidin-1-yl)­benz­amide

Akkurt, M.; Öztürk, S.; Önal, Z.; Altural, B.; Büyükgüngör, O.

doi:10.1107/S1600536804023050

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N-(5-Benzoyl-2-oxo-4-phenyl-1,2-dihydropyrimidin-1-yl)benzamide

M. Akkurt, S. Öztürk, Z. Önal, B. Altural and O. Büyükgüngör

The molecule of the title compound, C₂₄H₁₇N₃O₃, is non-planar. The pyrimidine ring is almost planar and makes dihedral angles of 72.47 (6), 64.77 (6) and 39.83 (5)° with the phenyl rings of the molecule. The molecules are linked through C—H

O and N—H

O interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804023050/ww6292sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804023050/ww6292Isup2.hkl Contains datablock I

CCDC reference: 253021

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.002 Å
R factor = 0.032
wR factor = 0.085
Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

N-(5-Benzoyl-2-oxo-4-phenyl-1,2-dihydropyrimidin-1-yl)benzamide top

Crystal data top

C₂₄H₁₇N₃O₃	F(000) = 824
M_r = 395.41	D_x = 1.379 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4211 reflections
a = 8.9688 (5) Å	θ = 1.9–27.3°
b = 10.9081 (4) Å	µ = 0.09 mm⁻¹
c = 19.8159 (11) Å	T = 150 K
β = 100.841 (4)°	Plate, yellow
V = 1904.04 (17) Å³	0.58 × 0.40 × 0.16 mm
Z = 4

Data collection top

Stoe IPDS-II diffractometer	4211 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3172 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.038
Detector resolution: 6.67 pixels mm^-1	θ_max = 27.2°, θ_min = 2.1°
ω scans	h = −11→11
Absorption correction: integration STOE X-RED32 (Stoe & Cie, 2002)	k = −13→13
T_min = 0.955, T_max = 0.985	l = −25→25
29930 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.032	All H-atom parameters refined
wR(F²) = 0.085	w = 1/[σ²(F_o²) + (0.052P)² + 0.0168P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
4211 reflections	Δρ_max = 0.18 e Å⁻³
340 parameters	Δρ_min = −0.13 e Å⁻³
0 restraints	Extinction correction: SHELXL97, FC^*=KFC[1.001XFC²Λ³/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0145 (13)

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^{2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted} ^R^-factors ^wR ^{and all goodnesses of fit} ^S ^{are based on} ^F2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of} ^F2 > σ(F^{2) is used only for calculating -}^R^-factor-obs ^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

	x	y	z	U_iso*/U_eq
O1	0.85676 (9)	0.62582 (7)	0.14423 (5)	0.0418 (3)
O2	0.50863 (10)	0.79559 (7)	0.30215 (4)	0.0409 (3)
O3	0.51146 (9)	0.64217 (7)	0.00892 (4)	0.0340 (2)
N1	0.67126 (10)	0.49045 (9)	0.10232 (5)	0.0314 (3)
N2	0.56556 (10)	0.57348 (8)	0.11919 (5)	0.0293 (3)
N3	0.38932 (10)	0.73350 (8)	0.08702 (5)	0.0301 (3)
C1	0.93002 (12)	0.44978 (10)	0.08708 (6)	0.0313 (3)
C2	1.08293 (14)	0.48082 (12)	0.10497 (7)	0.0413 (4)
C3	1.19166 (14)	0.41050 (12)	0.08226 (8)	0.0453 (4)
C4	1.14950 (14)	0.31089 (11)	0.04040 (7)	0.0412 (4)
C5	0.99821 (15)	0.27883 (12)	0.02245 (7)	0.0436 (4)
C6	0.88851 (13)	0.34726 (11)	0.04636 (6)	0.0383 (4)
C7	0.81985 (12)	0.53149 (10)	0.11268 (6)	0.0315 (3)
C8	0.55249 (12)	0.58260 (10)	0.18591 (6)	0.0303 (3)
C9	0.45887 (12)	0.66850 (10)	0.20525 (6)	0.0295 (3)
C10	0.46216 (12)	0.69555 (10)	0.28015 (6)	0.0306 (3)
C11	0.40679 (12)	0.60336 (10)	0.32422 (6)	0.0309 (3)
C12	0.35090 (12)	0.48935 (10)	0.29950 (6)	0.0337 (3)
C13	0.29858 (14)	0.40736 (12)	0.34322 (7)	0.0427 (4)
C14	0.29861 (17)	0.44028 (14)	0.41039 (8)	0.0532 (5)
C15	0.35242 (18)	0.55333 (14)	0.43505 (8)	0.0530 (5)
C16	0.40732 (15)	0.63468 (12)	0.39257 (6)	0.0406 (4)
C17	0.37499 (11)	0.74296 (10)	0.15193 (6)	0.0290 (3)
C18	0.26569 (12)	0.83595 (10)	0.16714 (6)	0.0306 (3)
C19	0.17098 (12)	0.81260 (11)	0.21388 (6)	0.0355 (3)
C20	0.07216 (14)	0.90172 (13)	0.22835 (7)	0.0423 (4)
C21	0.06821 (15)	1.01514 (13)	0.19706 (7)	0.0463 (4)
C22	0.16080 (15)	1.03925 (12)	0.15042 (7)	0.0439 (4)
C23	0.25845 (13)	0.94976 (11)	0.13456 (6)	0.0358 (3)
C24	0.48910 (11)	0.65173 (10)	0.06797 (5)	0.0292 (3)
H1	0.6324 (17)	0.4439 (13)	0.0661 (8)	0.046 (4)*
H2	1.1109 (17)	0.5564 (14)	0.1362 (8)	0.055 (4)*
H3	1.2977 (18)	0.4316 (14)	0.0962 (8)	0.057 (4)*
H4	1.2265 (17)	0.2618 (13)	0.0215 (8)	0.052 (4)*
H5	0.9661 (16)	0.2080 (14)	−0.0076 (8)	0.053 (4)*
H6	0.7820 (16)	0.3241 (12)	0.0330 (7)	0.044 (4)*
H8	0.6153 (14)	0.5256 (11)	0.2173 (7)	0.033 (3)*
H12	0.3487 (14)	0.4633 (12)	0.2511 (7)	0.040 (3)*
H13	0.2583 (15)	0.3283 (14)	0.3261 (7)	0.047 (4)*
H14	0.2595 (19)	0.3819 (15)	0.4406 (9)	0.065 (5)*
H15	0.354 (2)	0.5763 (16)	0.4826 (9)	0.072 (5)*
H16	0.4509 (17)	0.7166 (15)	0.4092 (8)	0.059 (4)*
H19	0.1726 (14)	0.7301 (12)	0.2357 (7)	0.039 (3)*
H20	0.0047 (17)	0.8817 (13)	0.2613 (8)	0.052 (4)*
H21	0.0019 (17)	1.0821 (15)	0.2075 (8)	0.058 (4)*
H22	0.1636 (17)	1.1216 (15)	0.1289 (8)	0.057 (4)*
H23	0.3284 (15)	0.9652 (12)	0.1018 (7)	0.039 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0381 (4)	0.0358 (5)	0.0523 (5)	−0.0030 (3)	0.0107 (4)	−0.0107 (4)
O2	0.0515 (5)	0.0348 (4)	0.0364 (5)	−0.0071 (4)	0.0084 (4)	−0.0047 (4)
O3	0.0376 (4)	0.0379 (4)	0.0272 (4)	−0.0007 (3)	0.0082 (3)	−0.0016 (3)
N1	0.0299 (4)	0.0328 (5)	0.0319 (5)	0.0028 (4)	0.0072 (4)	−0.0046 (4)
N2	0.0293 (4)	0.0306 (5)	0.0285 (5)	0.0026 (3)	0.0066 (3)	−0.0009 (4)
N3	0.0302 (4)	0.0315 (5)	0.0287 (5)	−0.0005 (4)	0.0058 (4)	−0.0006 (4)
C1	0.0330 (5)	0.0319 (6)	0.0293 (6)	0.0022 (4)	0.0066 (4)	0.0037 (4)
C2	0.0364 (6)	0.0383 (6)	0.0504 (8)	−0.0033 (5)	0.0115 (5)	−0.0034 (6)
C3	0.0334 (6)	0.0439 (7)	0.0606 (9)	−0.0015 (5)	0.0142 (6)	0.0011 (6)
C4	0.0420 (6)	0.0405 (7)	0.0441 (7)	0.0102 (5)	0.0155 (5)	0.0057 (5)
C5	0.0443 (7)	0.0425 (7)	0.0433 (7)	0.0080 (5)	0.0065 (5)	−0.0074 (6)
C6	0.0340 (6)	0.0394 (6)	0.0400 (7)	0.0033 (5)	0.0031 (5)	−0.0049 (5)
C7	0.0334 (5)	0.0309 (6)	0.0302 (6)	0.0002 (4)	0.0062 (4)	0.0011 (4)
C8	0.0319 (5)	0.0311 (5)	0.0277 (6)	−0.0012 (4)	0.0049 (4)	0.0004 (4)
C9	0.0310 (5)	0.0297 (5)	0.0284 (5)	−0.0029 (4)	0.0068 (4)	−0.0004 (4)
C10	0.0319 (5)	0.0296 (5)	0.0300 (6)	0.0024 (4)	0.0053 (4)	−0.0017 (4)
C11	0.0321 (5)	0.0317 (5)	0.0295 (6)	0.0050 (4)	0.0077 (4)	0.0019 (4)
C12	0.0335 (5)	0.0314 (6)	0.0370 (7)	0.0042 (4)	0.0084 (5)	0.0030 (5)
C13	0.0397 (6)	0.0347 (6)	0.0556 (8)	0.0043 (5)	0.0137 (6)	0.0112 (6)
C14	0.0590 (8)	0.0532 (8)	0.0529 (9)	0.0121 (7)	0.0245 (7)	0.0234 (7)
C15	0.0709 (9)	0.0575 (9)	0.0348 (7)	0.0142 (7)	0.0210 (7)	0.0105 (6)
C16	0.0505 (7)	0.0419 (7)	0.0296 (6)	0.0088 (5)	0.0083 (5)	0.0005 (5)
C17	0.0283 (5)	0.0287 (5)	0.0299 (6)	−0.0047 (4)	0.0056 (4)	−0.0009 (4)
C18	0.0292 (5)	0.0325 (6)	0.0292 (6)	−0.0005 (4)	0.0030 (4)	−0.0032 (4)
C19	0.0320 (5)	0.0392 (6)	0.0360 (6)	0.0007 (5)	0.0082 (5)	−0.0006 (5)
C20	0.0346 (6)	0.0520 (8)	0.0413 (7)	0.0046 (5)	0.0095 (5)	−0.0055 (6)
C21	0.0402 (7)	0.0472 (7)	0.0500 (8)	0.0123 (6)	0.0047 (6)	−0.0080 (6)
C22	0.0470 (7)	0.0358 (7)	0.0462 (8)	0.0077 (5)	0.0021 (6)	0.0007 (6)
C23	0.0377 (6)	0.0357 (6)	0.0330 (6)	0.0018 (5)	0.0042 (5)	0.0004 (5)
C24	0.0291 (5)	0.0305 (5)	0.0276 (6)	−0.0033 (4)	0.0043 (4)	−0.0005 (4)

Geometric parameters (Å, º) top

O1—C7	1.2171 (14)	C14—C15	1.380 (2)
O2—C10	1.2191 (13)	C15—C16	1.376 (2)
O3—C24	1.2282 (13)	C17—C18	1.4805 (15)
N1—N2	1.3964 (13)	C18—C23	1.3952 (16)
N1—C7	1.3841 (14)	C18—C19	1.3929 (16)
N2—C8	1.3528 (15)	C19—C20	1.3814 (18)
N2—C24	1.4026 (14)	C20—C21	1.381 (2)
N3—C17	1.3205 (15)	C21—C22	1.3790 (19)
N3—C24	1.3660 (14)	C22—C23	1.3865 (18)
N1—H1	0.895 (15)	C2—H2	1.033 (16)
C1—C2	1.3922 (17)	C3—H3	0.967 (16)
C1—C6	1.3883 (16)	C4—H4	1.001 (15)
C1—C7	1.4888 (16)	C5—H5	0.985 (15)
C2—C3	1.3809 (19)	C6—H6	0.975 (14)
C3—C4	1.3761 (19)	C8—H8	0.979 (13)
C4—C5	1.3815 (19)	C12—H12	0.997 (14)
C5—C6	1.3875 (18)	C13—H13	0.971 (15)
C8—C9	1.3605 (16)	C14—H14	0.983 (17)
C9—C10	1.5081 (16)	C15—H15	0.973 (18)
C9—C17	1.4293 (16)	C16—H16	1.006 (16)
C10—C11	1.4777 (16)	C19—H19	0.997 (13)
C11—C16	1.3960 (17)	C20—H20	0.994 (16)
C11—C12	1.3948 (16)	C21—H21	0.988 (16)
C12—C13	1.3869 (17)	C22—H22	0.997 (16)
C13—C14	1.379 (2)	C23—H23	0.998 (14)

O1···N2	2.6279 (12)	C23···C11ⁱ	3.4009 (16)
O1···C8	3.0330 (14)	C23···C12ⁱ	3.5281 (16)
O1···C24	3.3708 (13)	C24···O1	3.3708 (13)
O1···C13ⁱ	3.4007 (15)	C1···H20ⁱⁱ	3.043 (16)
O1···C21ⁱⁱ	3.3174 (17)	C2···H20ⁱⁱ	3.097 (15)
O2···C8ⁱ	3.1948 (13)	C4···H22^xii	2.697 (16)
O2···C18	3.1474 (14)	C5···H22^xii	2.901 (16)
O2···C19	3.2050 (14)	C6···H1	2.623 (15)
O2···C12ⁱ	3.3266 (14)	C7···H8	3.016 (13)
O3···C4ⁱⁱⁱ	3.4032 (15)	C8···H12	2.755 (13)
O3···C16^iv	3.3620 (15)	C8···H3^vii	3.093 (16)
O3···O3^v	3.1241 (11)	C9···H19	2.827 (13)
O3···N1^v	2.8772 (13)	C9···H12	2.674 (13)
O3···C7	3.3461 (14)	C10···H19	2.608 (13)
O3···N1	2.6871 (13)	C11···H23ⁱⁱ	2.958 (14)
O1···H13ⁱ	2.553 (15)	C11···H19	2.831 (13)
O1···H2	2.435 (16)	C16···H23ⁱⁱ	2.992 (14)
O2···H12ⁱ	2.570 (13)	C17···H2^vii	3.094 (15)
O2···H16	2.434 (16)	C20···H13^xi	3.064 (14)
O2···H3^vi	2.821 (16)	C21···H8ⁱ	3.023 (13)
O2···H8ⁱ	2.742 (12)	C22···H8ⁱ	2.991 (14)
O3···H1^v	2.009 (15)	C23···H8ⁱ	3.055 (14)
O3···H4ⁱⁱⁱ	2.742 (15)	C24···H3^vii	3.064 (16)
O3···H6^v	2.633 (14)	C24···H1^v	2.871 (15)
O3···H1	2.584 (15)	C24···H6^v	2.856 (14)
O3···H16^iv	2.484 (16)	H1···O3	2.584 (15)
N1···O3	2.6871 (13)	H1···C6	2.623 (15)
N1···O3^v	2.8772 (13)	H1···H6	2.07 (2)
N2···O1	2.6279 (12)	H1···O3^v	2.009 (15)
N3···C6^v	3.3902 (15)	H1···C24^v	2.871 (15)
N3···C13ⁱ	3.4478 (16)	H2···O1	2.435 (16)
N1···H6	2.584 (14)	H2···C17^xiii	3.094 (15)
N2···H3^vii	2.822 (16)	H3···N2^xiii	2.822 (16)
N3···H23	2.614 (13)	H3···C8^xiii	3.093 (16)
N3···H6^v	2.653 (14)	H3···C24^xiii	3.064 (16)
N3···H15^iv	2.905 (18)	H3···O2^xiv	2.821 (16)
C2···C6ⁱⁱⁱ	3.5866 (18)	H4···O3ⁱⁱⁱ	2.742 (15)
C4···O3ⁱⁱⁱ	3.4032 (15)	H4···H14^xv	2.30 (2)
C4···C7ⁱⁱⁱ	3.5422 (18)	H6···N1	2.584 (14)
C6···C2ⁱⁱⁱ	3.5866 (18)	H6···H1	2.07 (2)
C6···N3^v	3.3902 (15)	H6···O3^v	2.633 (15)
C7···O3	3.3461 (14)	H6···N3^v	2.653 (14)
C7···C4ⁱⁱⁱ	3.5422 (18)	H6···C24^v	2.856 (14)
C7···C20ⁱⁱ	3.4231 (18)	H8···C7	3.016 (13)
C8···O1	3.0330 (14)	H8···O2ⁱⁱ	2.742 (12)
C8···O2ⁱⁱ	3.1948 (13)	H8···C21ⁱⁱ	3.023 (13)
C8···C12	3.3017 (16)	H8···C22ⁱⁱ	2.991 (13)
C10···C19	2.9807 (16)	H8···C23ⁱⁱ	3.055 (14)
C11···C23ⁱⁱ	3.4009 (16)	H12···C8	2.755 (13)
C11···C19	3.5670 (16)	H12···C9	2.674 (13)
C12···C23ⁱⁱ	3.5281 (16)	H12···O2ⁱⁱ	2.570 (13)
C12···O2ⁱⁱ	3.3266 (14)	H13···O1ⁱⁱ	2.553 (15)
C12···C8	3.3017 (16)	H13···C20^viii	3.064 (14)
C13···C17ⁱⁱ	3.4192 (17)	H14···H4^xvi	2.30 (2)
C13···C21^viii	3.4429 (19)	H15···N3^x	2.905 (17)
C13···C20^viii	3.3612 (18)	H15···H23^x	2.46 (2)
C13···O1ⁱⁱ	3.4007 (15)	H16···O2	2.434 (16)
C13···N3ⁱⁱ	3.4478 (16)	H16···O3^x	2.484 (16)
C15···C15^ix	3.525 (2)	H19···C9	2.827 (13)
C16···O3^x	3.3620 (15)	H19···C10	2.608 (13)
C17···C13ⁱ	3.4192 (17)	H19···C11	2.831 (13)
C18···O2	3.1474 (14)	H20···C1ⁱ	3.043 (16)
C19···C10	2.9807 (16)	H20···C2ⁱ	3.097 (15)
C19···O2	3.2050 (14)	H22···C4^xvii	2.697 (16)
C19···C11	3.5670 (16)	H22···C5^xvii	2.901 (16)
C20···C13^xi	3.3612 (18)	H23···N3	2.614 (13)
C20···C7ⁱ	3.4231 (18)	H23···C11ⁱ	2.958 (14)
C21···C13^xi	3.4429 (19)	H23···C16ⁱ	2.992 (14)
C21···O1ⁱ	3.3174 (17)	H23···H15^iv	2.46 (2)

N2—N1—C7	115.65 (9)	C19—C20—C21	120.03 (12)
N1—N2—C8	117.98 (9)	C20—C21—C22	120.25 (13)
N1—N2—C24	118.88 (9)	C21—C22—C23	120.22 (12)
C8—N2—C24	122.82 (9)	C18—C23—C22	119.87 (11)
C17—N3—C24	120.60 (9)	N2—C24—N3	117.00 (9)
C7—N1—H1	121.4 (10)	O3—C24—N2	119.51 (10)
N2—N1—H1	112.4 (10)	O3—C24—N3	123.47 (10)
C2—C1—C7	116.92 (10)	C1—C2—H2	117.6 (9)
C2—C1—C6	119.18 (11)	C3—C2—H2	122.1 (9)
C6—C1—C7	123.90 (10)	C2—C3—H3	119.5 (9)
C1—C2—C3	120.27 (12)	C4—C3—H3	120.3 (9)
C2—C3—C4	120.28 (12)	C3—C4—H4	121.2 (9)
C3—C4—C5	120.02 (12)	C5—C4—H4	118.8 (9)
C4—C5—C6	120.08 (12)	C4—C5—H5	121.0 (9)
C1—C6—C5	120.13 (11)	C6—C5—H5	118.9 (9)
O1—C7—N1	120.72 (10)	C1—C6—H6	120.6 (8)
N1—C7—C1	115.98 (10)	C5—C6—H6	119.3 (8)
O1—C7—C1	123.18 (10)	N2—C8—H8	115.4 (8)
N2—C8—C9	119.83 (10)	C9—C8—H8	124.8 (8)
C8—C9—C17	116.75 (10)	C11—C12—H12	122.2 (8)
C10—C9—C17	121.77 (10)	C13—C12—H12	118.0 (8)
C8—C9—C10	120.87 (10)	C12—C13—H13	120.1 (8)
C9—C10—C11	120.13 (10)	C14—C13—H13	120.1 (8)
O2—C10—C9	117.98 (10)	C13—C14—H14	119.0 (10)
O2—C10—C11	121.88 (10)	C15—C14—H14	120.3 (10)
C12—C11—C16	119.63 (11)	C14—C15—H15	120.9 (10)
C10—C11—C12	122.53 (10)	C16—C15—H15	119.0 (10)
C10—C11—C16	117.82 (10)	C11—C16—H16	117.8 (9)
C11—C12—C13	119.81 (11)	C15—C16—H16	122.3 (9)
C12—C13—C14	119.77 (12)	C18—C19—H19	119.5 (8)
C13—C14—C15	120.75 (14)	C20—C19—H19	120.2 (8)
C14—C15—C16	120.08 (14)	C19—C20—H20	118.4 (8)
C11—C16—C15	119.95 (12)	C21—C20—H20	121.6 (8)
C9—C17—C18	121.03 (10)	C20—C21—H21	122.3 (9)
N3—C17—C18	116.19 (10)	C22—C21—H21	117.5 (9)
N3—C17—C9	122.79 (10)	C21—C22—H22	121.7 (9)
C17—C18—C19	121.34 (10)	C23—C22—H22	118.0 (9)
C17—C18—C23	119.37 (10)	C18—C23—H23	118.1 (8)
C19—C18—C23	119.29 (10)	C22—C23—H23	122.0 (8)
C18—C19—C20	120.31 (11)

C7—N1—N2—C8	−81.78 (12)	C10—C9—C17—C18	−11.22 (16)
C7—N1—N2—C24	92.00 (12)	C8—C9—C17—C18	177.70 (10)
N2—N1—C7—C1	−172.91 (9)	C8—C9—C10—O2	112.40 (13)
N2—N1—C7—O1	10.85 (16)	C17—C9—C10—C11	120.27 (12)
N1—N2—C24—N3	−178.50 (9)	C10—C9—C17—N3	168.89 (10)
C24—N2—C8—C9	1.77 (16)	C8—C9—C17—N3	−2.20 (16)
C8—N2—C24—O3	176.62 (10)	C9—C10—C11—C16	−177.78 (11)
C8—N2—C24—N3	−5.04 (15)	O2—C10—C11—C16	0.76 (17)
N1—N2—C24—O3	3.16 (15)	O2—C10—C11—C12	178.88 (11)
N1—N2—C8—C9	175.29 (10)	C9—C10—C11—C12	0.35 (16)
C17—N3—C24—O3	−177.13 (10)	C10—C11—C12—C13	−179.10 (11)
C24—N3—C17—C18	178.95 (9)	C10—C11—C16—C15	177.98 (12)
C17—N3—C24—N2	4.60 (15)	C12—C11—C16—C15	−0.21 (19)
C24—N3—C17—C9	−1.15 (16)	C16—C11—C12—C13	−1.01 (17)
C2—C1—C7—N1	−171.63 (11)	C11—C12—C13—C14	1.63 (19)
C7—C1—C6—C5	177.43 (11)	C12—C13—C14—C15	−1.0 (2)
C2—C1—C7—O1	4.51 (18)	C13—C14—C15—C16	−0.2 (2)
C7—C1—C2—C3	−179.01 (12)	C14—C15—C16—C11	0.8 (2)
C6—C1—C7—O1	−174.62 (12)	N3—C17—C18—C23	−40.68 (15)
C2—C1—C6—C5	−1.69 (18)	C9—C17—C18—C19	−39.91 (16)
C6—C1—C2—C3	0.17 (19)	C9—C17—C18—C23	139.41 (11)
C6—C1—C7—N1	9.24 (17)	N3—C17—C18—C19	140.00 (11)
C1—C2—C3—C4	1.6 (2)	C19—C18—C23—C22	1.87 (18)
C2—C3—C4—C5	−1.8 (2)	C23—C18—C19—C20	−0.71 (18)
C3—C4—C5—C6	0.3 (2)	C17—C18—C19—C20	178.62 (11)
C4—C5—C6—C1	1.49 (19)	C17—C18—C23—C22	−177.47 (11)
N2—C8—C9—C10	−169.35 (10)	C18—C19—C20—C21	−0.79 (19)
N2—C8—C9—C17	1.82 (16)	C19—C20—C21—C22	1.1 (2)
C8—C9—C10—C11	−69.01 (14)	C20—C21—C22—C23	0.1 (2)
C17—C9—C10—O2	−58.32 (15)	C21—C22—C23—C18	−1.55 (19)

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+2, −y+1, −z; (iv) x, −y+3/2, z−1/2; (v) −x+1, −y+1, −z; (vi) −x+2, y+1/2, −z+1/2; (vii) x−1, y, z; (viii) −x, y−1/2, −z+1/2; (ix) −x+1, −y+1, −z+1; (x) x, −y+3/2, z+1/2; (xi) −x, y+1/2, −z+1/2; (xii) x+1, y−1, z; (xiii) x+1, y, z; (xiv) −x+2, y−1/2, −z+1/2; (xv) x+1, −y+1/2, z−1/2; (xvi) x−1, −y+1/2, z+1/2; (xvii) x−1, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3^v	0.895 (15)	2.009 (15)	2.8772 (13)	163.4 (14)
C12—H12···O2ⁱⁱ	0.997 (14)	2.570 (13)	3.3266 (14)	132.6 (10)
C13—H13···O1ⁱⁱ	0.971 (15)	2.553 (15)	3.4007 (15)	145.9 (11)
C16—H16···O3^x	1.006 (16)	2.484 (16)	3.3620 (15)	145.6 (12)

Symmetry codes: (ii) −x+1, y−1/2, −z+1/2; (v) −x+1, −y+1, −z; (x) x, −y+3/2, z+1/2.

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