3-(Benzotriazol-1-yl) 5-ethyl 2,6-dimethyl-4-(3-nitro­phen­yl)-1,4-dihydro­pyridine-3,5-dicarboxyl­ate ethyl acetate hemisolvate

The title compound, C₂₃H₂₁N₅O₆·0.5C₄H₈O₂, is an important inter­mediate in the synthesis of nefidipine-type pharmaceuticals. The crystal packing is stabilized by inter­molecular N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 113 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in solvent or counterion
• R factor = 0.044
• wR factor = 0.120
• Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C26
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.19 Ratio

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

3-(Benzotriazol-1-yl)-5-ethyl-2,6-dimethyl-4-(3-nitrophenyl)- 1,4-dihydropyridine-3,5-dicarboxylate ethyl acetate hemisolvate

Crystal data

C23H21N5O6·0.5C4H8O2	Dx = 1.347 Mg m^−3
Mr = 507.50	Melting point = 459–460 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71070 Å
a = 10.2988 (13) Å	Cell parameters from 7583 reflections
b = 17.092 (2) Å	θ = 1.9–28.7°
c = 14.2211 (17) Å	µ = 0.10 mm^−1
β = 90.162 (4)°	T = 113 K
V = 2503.2 (5) Å^3	Block, colorless
Z = 4	0.22 × 0.18 × 0.14 mm
F(000) = 1064

Data collection

Rigaku Saturn diffractometer	5438 independent reflections
Radiation source: rotating anode	4048 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.046
Detector resolution: 7.31 pixels mm^-1	θmax = 27.0°, θmin = 1.9°
ω scans	h = −13→9
Absorption correction: multi-scan (Jacobson, 1998)	k = −21→21
Tmin = 0.973, Tmax = 0.986	l = −17→18
22057 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.120	w = 1/[σ^2(Fo^2) + (0.0708P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
5438 reflections	Δρmax = 0.29 e Å^−3
370 parameters	Δρmin = −0.32 e Å^−3
10 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0196 (16)

Special details

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	Occ. (<1)
O1	0.28657 (9)	0.45502 (6)	0.43373 (7)	0.0201 (2)
O2	0.13178 (11)	0.52817 (6)	0.35954 (8)	0.0301 (3)
O3	0.04282 (11)	0.16491 (7)	0.61631 (8)	0.0322 (3)
O4	0.23449 (10)	0.21671 (6)	0.57473 (7)	0.0228 (3)
O5	0.61363 (11)	0.30994 (7)	0.34904 (8)	0.0327 (3)
O6	0.62809 (11)	0.20348 (7)	0.26665 (9)	0.0377 (3)
N1	0.36996 (11)	0.51563 (7)	0.41517 (9)	0.0189 (3)
N2	0.38520 (12)	0.57294 (7)	0.47905 (8)	0.0211 (3)
N3	0.47897 (12)	0.61820 (7)	0.44871 (9)	0.0208 (3)
N4	−0.12128 (13)	0.33610 (8)	0.42691 (9)	0.0222 (3)
N5	0.56480 (12)	0.25306 (8)	0.30877 (9)	0.0233 (3)
C1	0.45383 (13)	0.52090 (8)	0.34167 (10)	0.0176 (3)
C2	0.52417 (14)	0.58817 (8)	0.36441 (10)	0.0179 (3)
C3	0.62195 (15)	0.61548 (9)	0.30419 (11)	0.0220 (3)
H3	0.6721	0.6605	0.3190	0.026*
C4	0.64152 (15)	0.57402 (9)	0.22281 (11)	0.0254 (4)
H4	0.7058	0.5913	0.1798	0.031*
C5	0.56860 (16)	0.50635 (9)	0.20131 (12)	0.0275 (4)
H5A	0.5855	0.4796	0.1441	0.033*
C6	0.47428 (15)	0.47766 (9)	0.25987 (11)	0.0243 (4)
H6A	0.4263	0.4316	0.2457	0.029*
C7	0.15788 (14)	0.46796 (8)	0.39854 (10)	0.0184 (3)
C8	−0.04865 (14)	0.39962 (9)	0.40125 (10)	0.0186 (3)
C9	0.08145 (14)	0.39931 (8)	0.41990 (10)	0.0169 (3)
C10	0.14803 (13)	0.32664 (8)	0.45939 (10)	0.0164 (3)
H10	0.2119	0.3441	0.5081	0.020*
C11	0.05066 (14)	0.27271 (8)	0.50695 (10)	0.0187 (3)
C12	−0.07737 (14)	0.27665 (9)	0.48529 (10)	0.0202 (3)
C13	−0.12437 (15)	0.46458 (9)	0.35544 (11)	0.0241 (4)
H13A	−0.2166	0.4506	0.3534	0.036*
H13B	−0.0926	0.4727	0.2913	0.036*
H13C	−0.1132	0.5129	0.3918	0.036*
C14	−0.18369 (16)	0.22246 (10)	0.51614 (12)	0.0289 (4)
H14A	−0.2051	0.1864	0.4648	0.043*
H14B	−0.2608	0.2530	0.5326	0.043*
H14C	−0.1546	0.1926	0.5711	0.043*
C15	0.22301 (14)	0.28247 (8)	0.38299 (10)	0.0162 (3)
C16	0.35766 (14)	0.28793 (8)	0.37917 (10)	0.0168 (3)
H16	0.4037	0.3199	0.4225	0.020*
C17	0.42318 (13)	0.24594 (8)	0.31116 (10)	0.0181 (3)
C18	0.36254 (15)	0.19751 (9)	0.24684 (11)	0.0242 (4)
H18	0.4108	0.1686	0.2019	0.029*
C19	0.22839 (16)	0.19299 (10)	0.25078 (11)	0.0283 (4)
H19	0.1829	0.1609	0.2072	0.034*
C20	0.15983 (15)	0.23490 (9)	0.31783 (10)	0.0231 (4)
H20	0.0678	0.2311	0.3193	0.028*
C21	0.10319 (15)	0.21264 (9)	0.57118 (11)	0.0212 (3)
C22	0.29988 (16)	0.16085 (10)	0.63541 (12)	0.0307 (4)
H22A	0.2764	0.1068	0.6172	0.037*
H22B	0.2741	0.1692	0.7017	0.037*
C23	0.44317 (16)	0.17342 (10)	0.62439 (13)	0.0351 (4)
H23A	0.4678	0.1642	0.5588	0.053*
H23B	0.4904	0.1370	0.6653	0.053*
H23C	0.4650	0.2273	0.6419	0.053*
O7	0.3476 (3)	0.9531 (2)	0.5426 (2)	0.0735 (10)	0.50
O8	0.5451 (5)	0.9963 (3)	0.4967 (4)	0.0479 (15)	0.50
C24	0.3546 (7)	1.0284 (6)	0.4006 (5)	0.067 (2)	0.50
H24A	0.2630	1.0178	0.3987	0.100*	0.50
H24B	0.3684	1.0837	0.4070	0.100*	0.50
H24C	0.3939	1.0104	0.3434	0.100*	0.50
C25	0.4145 (8)	0.9875 (6)	0.4850 (6)	0.066 (3)	0.50
C26	0.5988 (7)	0.9633 (5)	0.5803 (5)	0.0466 (16)	0.50
H26A	0.5923	0.9073	0.5785	0.056*	0.50
H26B	0.5527	0.9822	0.6343	0.056*	0.50
C27	0.7416 (6)	0.9884 (5)	0.5822 (6)	0.109 (3)	0.50
H27A	0.7814	0.9674	0.6378	0.164*	0.50
H27B	0.7862	0.9693	0.5276	0.164*	0.50
H27C	0.7464	1.0445	0.5837	0.164*	0.50
H4A	−0.2027 (19)	0.3390 (12)	0.4154 (13)	0.042 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0137 (5)	0.0167 (5)	0.0298 (6)	−0.0044 (4)	−0.0008 (4)	0.0045 (4)
O2	0.0231 (6)	0.0228 (6)	0.0442 (7)	−0.0014 (5)	−0.0039 (5)	0.0122 (5)
O3	0.0275 (6)	0.0284 (6)	0.0407 (7)	−0.0014 (5)	0.0069 (5)	0.0149 (5)
O4	0.0195 (6)	0.0244 (6)	0.0246 (6)	0.0020 (4)	−0.0004 (4)	0.0079 (5)
O5	0.0170 (6)	0.0484 (8)	0.0328 (7)	−0.0064 (5)	−0.0009 (5)	−0.0110 (6)
O6	0.0260 (7)	0.0379 (7)	0.0492 (8)	0.0133 (5)	0.0110 (6)	−0.0049 (6)
N1	0.0162 (6)	0.0161 (6)	0.0244 (7)	−0.0043 (5)	0.0022 (5)	−0.0010 (5)
N2	0.0202 (7)	0.0216 (7)	0.0215 (7)	−0.0036 (5)	−0.0013 (5)	−0.0028 (5)
N3	0.0178 (7)	0.0222 (7)	0.0223 (7)	−0.0042 (5)	0.0000 (5)	−0.0008 (5)
N4	0.0120 (7)	0.0278 (7)	0.0268 (7)	−0.0030 (5)	−0.0014 (5)	0.0041 (6)
N5	0.0178 (7)	0.0295 (7)	0.0225 (7)	0.0037 (6)	0.0028 (6)	0.0005 (6)
C1	0.0139 (7)	0.0164 (7)	0.0225 (8)	0.0008 (6)	−0.0003 (6)	0.0029 (6)
C2	0.0138 (7)	0.0175 (7)	0.0224 (8)	0.0006 (6)	−0.0032 (6)	0.0018 (6)
C3	0.0173 (8)	0.0186 (7)	0.0301 (9)	−0.0017 (6)	0.0003 (6)	0.0030 (6)
C4	0.0218 (8)	0.0247 (8)	0.0298 (9)	0.0011 (7)	0.0076 (7)	0.0038 (7)
C5	0.0314 (9)	0.0236 (8)	0.0276 (9)	0.0025 (7)	0.0071 (7)	−0.0048 (7)
C6	0.0261 (9)	0.0175 (7)	0.0295 (9)	−0.0008 (6)	0.0021 (7)	−0.0042 (6)
C7	0.0146 (7)	0.0201 (7)	0.0206 (8)	0.0017 (6)	0.0004 (6)	0.0004 (6)
C8	0.0165 (8)	0.0221 (8)	0.0172 (7)	−0.0002 (6)	0.0009 (6)	0.0000 (6)
C9	0.0143 (7)	0.0185 (7)	0.0180 (7)	−0.0006 (6)	0.0007 (6)	0.0000 (6)
C10	0.0139 (7)	0.0168 (7)	0.0185 (7)	−0.0024 (6)	−0.0011 (6)	0.0004 (6)
C11	0.0188 (8)	0.0189 (7)	0.0185 (7)	−0.0021 (6)	0.0026 (6)	0.0000 (6)
C12	0.0180 (8)	0.0217 (8)	0.0209 (8)	−0.0035 (6)	0.0024 (6)	−0.0001 (6)
C13	0.0185 (8)	0.0285 (9)	0.0252 (8)	0.0025 (7)	−0.0018 (6)	0.0031 (7)
C14	0.0198 (8)	0.0331 (9)	0.0337 (9)	−0.0091 (7)	0.0003 (7)	0.0065 (7)
C15	0.0167 (8)	0.0150 (7)	0.0168 (7)	−0.0009 (6)	0.0000 (6)	0.0028 (6)
C16	0.0151 (7)	0.0164 (7)	0.0189 (7)	−0.0014 (6)	−0.0022 (6)	0.0000 (6)
C17	0.0132 (7)	0.0191 (7)	0.0219 (8)	0.0005 (6)	0.0014 (6)	0.0022 (6)
C18	0.0276 (9)	0.0221 (8)	0.0230 (8)	−0.0012 (7)	0.0047 (7)	−0.0055 (6)
C19	0.0257 (9)	0.0313 (9)	0.0278 (9)	−0.0091 (7)	−0.0009 (7)	−0.0097 (7)
C20	0.0167 (8)	0.0276 (8)	0.0250 (8)	−0.0069 (6)	0.0000 (6)	−0.0017 (7)
C21	0.0210 (8)	0.0199 (7)	0.0227 (8)	−0.0012 (6)	0.0041 (6)	−0.0004 (6)
C22	0.0291 (9)	0.0317 (9)	0.0313 (9)	0.0100 (7)	0.0026 (7)	0.0112 (7)
C23	0.0281 (10)	0.0305 (9)	0.0466 (11)	0.0074 (7)	−0.0061 (8)	0.0053 (8)
O7	0.071 (2)	0.084 (3)	0.066 (2)	−0.011 (2)	0.0232 (19)	0.0087 (19)
O8	0.084 (5)	0.031 (3)	0.029 (2)	0.011 (3)	0.005 (3)	0.005 (2)
C24	0.074 (7)	0.074 (5)	0.051 (4)	0.013 (5)	−0.030 (4)	0.004 (4)
C25	0.096 (7)	0.048 (4)	0.053 (4)	0.004 (4)	0.016 (4)	−0.020 (3)
C26	0.067 (5)	0.037 (3)	0.035 (3)	0.005 (3)	−0.023 (3)	0.008 (2)
C27	0.083 (5)	0.112 (6)	0.132 (6)	−0.038 (4)	−0.066 (5)	0.025 (4)

Geometric parameters (Å, º)

O1—N1	1.3718 (14)	C14—H14B	0.9800
O1—C7	1.4326 (17)	C14—H14C	0.9800
O2—C7	1.1991 (17)	C15—C16	1.3910 (19)
O3—C21	1.2109 (18)	C15—C20	1.393 (2)
O4—C21	1.3548 (18)	C16—C17	1.3819 (19)
O4—C22	1.4514 (19)	C16—H16	0.9500
O5—N5	1.2346 (17)	C17—C18	1.382 (2)
O6—N5	1.2263 (16)	C18—C19	1.385 (2)
N1—N2	1.3448 (17)	C18—H18	0.9500
N1—C1	1.3608 (18)	C19—C20	1.387 (2)
N2—N3	1.3113 (17)	C19—H19	0.9500
N3—C2	1.3859 (19)	C20—H20	0.9500
N4—C8	1.3685 (19)	C22—C23	1.500 (2)
N4—C12	1.3872 (19)	C22—H22A	0.9900
N4—H4A	0.86 (2)	C22—H22B	0.9900
N5—C17	1.4641 (18)	C23—H23A	0.9800
C1—C6	1.395 (2)	C23—H23B	0.9800
C1—C2	1.3963 (19)	C23—H23C	0.9800
C2—C3	1.404 (2)	O7—C25	1.223 (8)
C3—C4	1.372 (2)	O7—O8^i	1.511 (6)
C3—H3	0.9500	O8—C25^i	0.563 (9)
C4—C5	1.412 (2)	O8—O8^i	0.943 (11)
C4—H4	0.9500	O8—C25	1.364 (6)
C5—C6	1.372 (2)	O8—C26	1.425 (6)
C5—H5A	0.9500	O8—O7^i	1.511 (6)
C6—H6A	0.9500	O8—C24^i	1.835 (8)
C7—C9	1.4458 (19)	C24—C26^i	0.569 (8)
C8—C9	1.365 (2)	C24—C27^i	1.060 (10)
C8—C13	1.504 (2)	C24—C25	1.519 (7)
C9—C10	1.5250 (19)	C24—O8^i	1.836 (8)
C10—C11	1.5221 (19)	C24—H24A	0.9600
C10—C15	1.5335 (19)	C24—H24B	0.9600
C10—H10	1.0000	C24—H24C	0.9599
C11—C12	1.355 (2)	C26—C27	1.532 (6)
C11—C21	1.476 (2)	C26—H26A	0.9600
C12—C14	1.501 (2)	C26—H26B	0.9600
C13—H13A	0.9800	C27—H27A	0.9600
C13—H13B	0.9800	C27—H27B	0.9601
C13—H13C	0.9800	C27—H27C	0.9600
C14—H14A	0.9800
N1—O1—C7	113.28 (10)	H14A—C14—H14B	109.5
C21—O4—C22	116.73 (12)	C12—C14—H14C	109.5
N2—N1—C1	113.42 (11)	H14A—C14—H14C	109.5
N2—N1—O1	119.47 (11)	H14B—C14—H14C	109.5
C1—N1—O1	126.65 (12)	C16—C15—C20	118.50 (13)
N3—N2—N1	106.98 (11)	C16—C15—C10	119.91 (12)
N2—N3—C2	108.40 (11)	C20—C15—C10	121.57 (13)
C8—N4—C12	124.28 (13)	C17—C16—C15	118.77 (13)
C8—N4—H4A	116.1 (14)	C17—C16—H16	120.6
C12—N4—H4A	118.3 (14)	C15—C16—H16	120.6
O6—N5—O5	123.66 (13)	C18—C17—C16	123.63 (14)
O6—N5—C17	119.00 (13)	C18—C17—N5	118.88 (13)
O5—N5—C17	117.33 (12)	C16—C17—N5	117.49 (13)
N1—C1—C6	134.69 (14)	C17—C18—C19	117.11 (14)
N1—C1—C2	101.93 (12)	C17—C18—H18	121.4
C6—C1—C2	123.37 (14)	C19—C18—H18	121.4
N3—C2—C1	109.27 (12)	C18—C19—C20	120.58 (14)
N3—C2—C3	130.38 (13)	C18—C19—H19	119.7
C1—C2—C3	120.34 (14)	C20—C19—H19	119.7
C4—C3—C2	116.75 (14)	C19—C20—C15	121.40 (14)
C4—C3—H3	121.6	C19—C20—H20	119.3
C2—C3—H3	121.6	C15—C20—H20	119.3
C3—C4—C5	121.75 (15)	O3—C21—O4	121.92 (14)
C3—C4—H4	119.1	O3—C21—C11	127.51 (15)
C5—C4—H4	119.1	O4—C21—C11	110.57 (12)
C6—C5—C4	122.57 (15)	O4—C22—C23	107.37 (13)
C6—C5—H5A	118.7	O4—C22—H22A	110.2
C4—C5—H5A	118.7	C23—C22—H22A	110.2
C5—C6—C1	115.20 (14)	O4—C22—H22B	110.2
C5—C6—H6A	122.4	C23—C22—H22B	110.2
C1—C6—H6A	122.4	H22A—C22—H22B	108.5
O2—C7—O1	120.01 (13)	C22—C23—H23A	109.5
O2—C7—C9	132.24 (14)	C22—C23—H23B	109.5
O1—C7—C9	107.75 (12)	H23A—C23—H23B	109.5
C9—C8—N4	118.81 (13)	C22—C23—H23C	109.5
C9—C8—C13	126.47 (13)	H23A—C23—H23C	109.5
N4—C8—C13	114.71 (13)	H23B—C23—H23C	109.5
C8—C9—C7	119.38 (13)	C25—O8—C26	116.0 (4)
C8—C9—C10	120.98 (12)	C25—C24—H24A	109.4
C7—C9—C10	119.60 (12)	C25—C24—H24B	108.6
C11—C10—C9	111.15 (11)	H24A—C24—H24B	109.5
C11—C10—C15	110.52 (11)	C25—C24—H24C	110.5
C9—C10—C15	111.52 (11)	H24A—C24—H24C	109.5
C11—C10—H10	107.8	H24B—C24—H24C	109.5
C9—C10—H10	107.8	O7—C25—O8	121.9 (5)
C15—C10—H10	107.8	O7—C25—C24	121.5 (7)
C12—C11—C21	122.01 (13)	O8—C25—C24	116.4 (5)
C12—C11—C10	120.72 (13)	O8—C26—C27	105.9 (5)
C21—C11—C10	117.10 (13)	O8—C26—H26A	110.3
C11—C12—N4	119.20 (13)	C27—C26—H26A	110.3
C11—C12—C14	127.83 (14)	O8—C26—H26B	110.0
N4—C12—C14	112.96 (13)	C27—C26—H26B	111.6
C8—C13—H13A	109.5	H26A—C26—H26B	108.7
C8—C13—H13B	109.5	C26—C27—H27A	108.5
H13A—C13—H13B	109.5	C26—C27—H27B	110.6
C8—C13—H13C	109.5	H27A—C27—H27B	109.5
H13A—C13—H13C	109.5	C26—C27—H27C	109.3
H13B—C13—H13C	109.5	H27A—C27—H27C	109.5
C12—C14—H14A	109.5	H27B—C27—H27C	109.5
C12—C14—H14B	109.5
C7—O1—N1—N2	92.51 (14)	C9—C10—C11—C12	21.75 (19)
C7—O1—N1—C1	−95.77 (16)	C15—C10—C11—C12	−102.63 (16)
C1—N1—N2—N3	0.68 (16)	C9—C10—C11—C21	−162.93 (12)
O1—N1—N2—N3	173.44 (11)	C15—C10—C11—C21	72.69 (16)
N1—N2—N3—C2	−0.53 (15)	C21—C11—C12—N4	177.88 (13)
N2—N1—C1—C6	−178.83 (16)	C10—C11—C12—N4	−7.0 (2)
O1—N1—C1—C6	9.0 (3)	C21—C11—C12—C14	−3.0 (2)
N2—N1—C1—C2	−0.51 (16)	C10—C11—C12—C14	172.11 (14)
O1—N1—C1—C2	−172.66 (12)	C8—N4—C12—C11	−11.4 (2)
N2—N3—C2—C1	0.22 (17)	C8—N4—C12—C14	169.32 (14)
N2—N3—C2—C3	179.30 (15)	C11—C10—C15—C16	−131.81 (14)
N1—C1—C2—N3	0.17 (15)	C9—C10—C15—C16	104.02 (15)
C6—C1—C2—N3	178.74 (13)	C11—C10—C15—C20	46.58 (18)
N1—C1—C2—C3	−179.01 (13)	C9—C10—C15—C20	−77.59 (16)
C6—C1—C2—C3	−0.4 (2)	C20—C15—C16—C17	−0.1 (2)
N3—C2—C3—C4	−177.63 (15)	C10—C15—C16—C17	178.34 (13)
C1—C2—C3—C4	1.4 (2)	C15—C16—C17—C18	−0.9 (2)
C2—C3—C4—C5	−1.1 (2)	C15—C16—C17—N5	179.83 (12)
C3—C4—C5—C6	−0.1 (3)	O6—N5—C17—C18	−17.2 (2)
C4—C5—C6—C1	1.0 (2)	O5—N5—C17—C18	162.03 (14)
N1—C1—C6—C5	177.27 (16)	O6—N5—C17—C16	162.08 (14)
C2—C1—C6—C5	−0.8 (2)	O5—N5—C17—C16	−18.70 (19)
N1—O1—C7—O2	−1.81 (19)	C16—C17—C18—C19	1.4 (2)
N1—O1—C7—C9	178.20 (11)	N5—C17—C18—C19	−179.36 (13)
C12—N4—C8—C9	11.8 (2)	C17—C18—C19—C20	−0.9 (2)
C12—N4—C8—C13	−167.30 (14)	C18—C19—C20—C15	−0.1 (2)
N4—C8—C9—C7	−176.15 (13)	C16—C15—C20—C19	0.6 (2)
C13—C8—C9—C7	2.8 (2)	C10—C15—C20—C19	−177.83 (14)
N4—C8—C9—C10	6.2 (2)	C22—O4—C21—O3	0.1 (2)
C13—C8—C9—C10	−174.85 (13)	C22—O4—C21—C11	−179.99 (12)
O2—C7—C9—C8	−5.9 (3)	C12—C11—C21—O3	−5.5 (2)
O1—C7—C9—C8	174.07 (12)	C10—C11—C21—O3	179.21 (15)
O2—C7—C9—C10	171.77 (16)	C12—C11—C21—O4	174.51 (13)
O1—C7—C9—C10	−8.24 (17)	C10—C11—C21—O4	−0.75 (18)
C8—C9—C10—C11	−21.40 (18)	C21—O4—C22—C23	177.13 (13)
C7—C9—C10—C11	160.95 (13)	C26—O8—C25—O7	−0.1 (9)
C8—C9—C10—C15	102.41 (15)	C26—O8—C25—C24	174.9 (11)
C7—C9—C10—C15	−75.24 (16)	C25—O8—C26—C27	−174.1 (6)

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O5^ii	0.86 (2)	2.17 (2)	2.9770 (18)	157.4 (18)

Symmetry code: (ii) x−1, y, z.