Interplay between packing, dimer interaction energy and morphology in a series of tricyclic imide crystals

Crystal morphology is a very important feature in many industrial applications. Tricyclic imides, derivatives of 10-oxa-4-azatricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione with differing small hydrophobic groups (Me, Et), were studied and grouped based on Etter's rule. Using experimental X-ray studies, dimer energy calculations, framework analysis and periodic DFT-D calculations, it is shown that knowledge of the hydrogen-bond pattern can be used to determine the final crystal shape. Molecules forming a ring hydrogen-bond motif crystallize as plate crystals with the {100} facet as the slowest growing, whereas those molecules forming an infinite hydrogen-bond motif in the crystal structure crystallize as needles with the {101} facet having the largest surface area.

Computing details

For all structures, program(s) used to refine structure: MoPro (J. Appl. Cryst. 2005, 38, 38-54).

10-oxa-4-azatricyclo[5.2.1.0^{2,6}]dec-8-ene-3,5-dione (P7_1)

Crystal data

C8H7NO3	F(000) = 344
Mr = 165.14	Dx = 1.571 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.7958 (2) Å	Cell parameters from 6000 reflections
b = 7.5909 (2) Å	θ = 3–35.0°
c = 10.8134 (3) Å	µ = 0.12 mm^−1
β = 104.722 (1)°	T = 100 K
V = 698.29 (3) Å^3	Block, colorless
Z = 4	0.2 × 0.1 × 0.1 mm

Data collection

Bruker Apex II Ultra diffractometer	5590 reflections with I > 2.0σ(I)
Radiation source: rotating anode	Rint = 0.030
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38	θmax = 48.5°, θmin = 3.3°
Tmin = 0.882, Tmax = 0.997	h = −18→17
35114 measured reflections	k = 0→15
6512 independent reflections	l = 0→22

Refinement

Refinement on F^2	14 restraints
Least-squares matrix: full	Primary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.025	Secondary atom site location: difference Fourier map
wR(F^2) = 0.058	Hydrogen site location: difference Fourier map
S = 1.28	All H-atom parameters refined
6512 reflections	Weighting scheme based on measured s.u.'s
137 parameters	(Δ/σ)max = −0.002

Special details

Refinement. Refinement of F² against reflections. The threshold expression of F² > 2sigma(F²) is used for calculating R-factors(gt) 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
O2	0.87512 (3)	0.55971 (3)	0.13236 (2)	0.01630 (2)
O1	1.21114 (3)	0.44109 (3)	0.51846 (2)	0.01623 (2)
O3	1.27034 (3)	0.72857 (3)	0.24908 (2)	0.01478 (2)
N1	1.01515 (3)	0.49754 (3)	0.33751 (2)	0.01322 (2)
H1	0.9273 (5)	0.5204 (8)	0.3828 (5)	0.0204 (3)*
C1	1.16634 (3)	0.45550 (3)	0.40243 (2)	0.01230 (2)
C8	1.26557 (3)	0.43591 (3)	0.30786 (2)	0.01196 (2)
H8	1.3257 (5)	0.3082 (4)	0.3233 (5)	0.0147 (2)*
C2	0.99529 (3)	0.51161 (4)	0.20653 (2)	0.01197 (2)
C3	1.14953 (3)	0.46647 (3)	0.17597 (2)	0.01149 (2)
H3	1.1352 (7)	0.3585 (5)	0.1064 (4)	0.01420 (19)*
C4	1.21935 (3)	0.63549 (4)	0.12982 (3)	0.01323 (2)
H4	1.1328 (5)	0.7098 (6)	0.0576 (4)	0.0165 (2)*
C7	1.37930 (3)	0.59637 (4)	0.31359 (3)	0.01436 (3)
H7	1.4426 (6)	0.6365 (7)	0.4105 (2)	0.0175 (2)*
C6	1.47341 (3)	0.55691 (4)	0.21702 (3)	0.01617 (3)
H6	1.5907 (3)	0.5021 (7)	0.2427 (6)	0.0202 (3)*
C5	1.37314 (3)	0.58201 (4)	0.10239 (3)	0.01588 (3)
H5	1.3852 (7)	0.5536 (7)	0.0073 (2)	0.0201 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.01251 (7)	0.02299 (10)	0.01302 (8)	0.00201 (6)	0.00255 (6)	0.00306 (6)
O1	0.01501 (8)	0.02290 (10)	0.01058 (7)	0.00275 (7)	0.00287 (6)	0.00019 (6)
O3	0.01475 (8)	0.01065 (7)	0.01958 (8)	−0.00040 (6)	0.00557 (6)	−0.00180 (6)
N1	0.01182 (7)	0.01750 (9)	0.01079 (7)	0.00146 (6)	0.00372 (6)	0.00069 (6)
C1	0.01268 (8)	0.01398 (9)	0.01030 (8)	0.00109 (7)	0.00304 (6)	0.00003 (6)
C8	0.01203 (8)	0.01225 (9)	0.01187 (8)	0.00132 (6)	0.00355 (6)	0.00010 (6)
C2	0.01129 (8)	0.01386 (9)	0.01075 (8)	−0.00005 (7)	0.00277 (6)	0.00054 (6)
C3	0.01191 (8)	0.01186 (8)	0.01111 (8)	−0.00011 (6)	0.00367 (6)	−0.00059 (6)
C4	0.01272 (9)	0.01303 (9)	0.01477 (9)	0.00069 (7)	0.00502 (7)	0.00213 (7)
C7	0.01191 (8)	0.01521 (10)	0.01558 (10)	−0.00098 (7)	0.00279 (7)	−0.00153 (7)
C6	0.01165 (9)	0.01812 (11)	0.01935 (11)	0.00050 (7)	0.00509 (8)	0.00086 (8)
C5	0.01361 (9)	0.01860 (11)	0.01707 (10)	0.00047 (8)	0.00692 (8)	0.00145 (8)

Geometric parameters (Å, º)

O2—C2	1.2095 (3)	C2—C3	1.5149 (4)
O1—C1	1.2207 (3)	C3—C4	1.5582 (4)
O3—C4	1.4385 (4)	C3—H3	1.0977 (13)
O3—C7	1.4396 (4)	C4—C5	1.5121 (4)
N1—C1	1.3743 (4)	C4—H4	1.0976 (13)
N1—C2	1.3864 (3)	C7—C6	1.5181 (4)
N1—H1	1.0289 (14)	C7—H7	1.0975 (13)
C1—C8	1.5111 (4)	C6—C5	1.3398 (4)
C8—C7	1.5674 (4)	C6—H6	1.0810 (13)
C8—C3	1.5458 (4)	C5—H5	1.0822 (13)
C8—H8	1.0967 (13)
C4—O3—C7	96.29 (2)	C4—C3—H3	112.4 (3)
C1—N1—C2	113.21 (2)	C8—C3—H3	117.0 (2)
C1—N1—H1	122.8 (3)	O3—C4—C3	100.13 (2)
C2—N1—H1	123.9 (3)	O3—C4—C5	102.54 (2)
O1—C1—N1	124.31 (2)	O3—C4—H4	112.8 (3)
O1—C1—C8	126.56 (2)	C3—C4—C5	106.67 (2)
N1—C1—C8	109.12 (2)	C3—C4—H4	113.1 (3)
C1—C8—C7	111.68 (2)	C5—C4—H4	119.5 (3)
C1—C8—C3	104.48 (2)	O3—C7—C8	100.54 (2)
C1—C8—H8	108.9 (3)	O3—C7—C6	102.50 (2)
C7—C8—C3	100.659 (19)	O3—C7—H7	112.5 (3)
C7—C8—H8	113.7 (3)	C8—C7—C6	105.88 (2)
C3—C8—H8	117.0 (2)	C8—C7—H7	114.7 (3)
O2—C2—N1	124.24 (2)	C6—C7—H7	118.6 (3)
O2—C2—C3	127.14 (2)	C7—C6—C5	105.22 (2)
N1—C2—C3	108.55 (2)	C7—C6—H6	123.4 (3)
C2—C3—C4	109.35 (2)	C5—C6—H6	130.8 (2)
C2—C3—C8	104.514 (19)	C4—C5—C6	105.55 (2)
C2—C3—H3	111.4 (3)	C4—C5—H5	123.3 (3)
C4—C3—C8	101.390 (19)	C6—C5—H5	130.6 (2)
O2—C2—N1—C1	−174.44 (4)	C8—C7—O3—C4	−60.07 (5)
O2—C2—N1—H1	3.4 (5)	C8—C7—C6—C5	73.64 (5)
O2—C2—C3—C4	65.50 (4)	C8—C7—C6—H6	−98.5 (6)
O2—C2—C3—C8	173.39 (4)	C8—C3—C4—C5	69.45 (4)
O2—C2—C3—H3	−59.4 (6)	C8—C3—C4—H4	−157.3 (6)
O1—C1—N1—C2	177.98 (4)	H8—C8—C7—C6	54.9 (6)
O1—C1—N1—H1	0.1 (6)	H8—C8—C7—H7	−77.8 (8)
O1—C1—C8—C7	−72.29 (4)	H8—C8—C3—C2	123.6 (6)
O1—C1—C8—C3	179.76 (4)	H8—C8—C3—C4	−122.8 (6)
O1—C1—C8—H8	54.1 (6)	H8—C8—C3—H3	−0.1 (7)
O3—C4—C3—C2	72.95 (4)	C2—C3—C4—C5	179.43 (4)
O3—C4—C3—C8	−37.03 (6)	C2—C3—C4—H4	−47.3 (6)
O3—C4—C3—H3	−162.8 (6)	C2—C3—C8—C7	−112.71 (4)
O3—C4—C5—C6	31.75 (7)	C3—C4—O3—C7	60.60 (4)
O3—C4—C5—H5	−156.3 (7)	C3—C4—C5—C6	−73.00 (5)
O3—C7—C8—C1	−75.02 (4)	C3—C4—C5—H5	98.9 (6)
O3—C7—C8—C3	35.39 (6)	C3—C8—C7—C6	−70.98 (4)
O3—C7—C8—H8	161.3 (6)	C3—C8—C7—H7	156.3 (7)
O3—C7—C6—C5	−31.30 (7)	H3—C3—C4—C5	−56.3 (6)
O3—C7—C6—H6	156.6 (7)	H3—C3—C4—H4	77.0 (8)
N1—C1—C8—C7	106.12 (4)	H3—C3—C8—C7	123.6 (6)
N1—C1—C8—C3	−1.83 (4)	C4—O3—C7—C6	48.98 (5)
N1—C1—C8—H8	−127.5 (5)	C4—O3—C7—H7	177.5 (5)
N1—C2—C3—C4	−111.48 (5)	C4—C3—C8—C7	0.95 (4)
N1—C2—C3—C8	−3.60 (4)	C4—C5—C6—C7	−0.24 (4)
N1—C2—C3—H3	123.7 (5)	C4—C5—C6—H6	171.0 (6)
H1—N1—C1—C8	−178.4 (4)	H4—C4—O3—C7	−178.9 (5)
H1—N1—C2—C3	−179.5 (4)	H4—C4—C5—C6	157.3 (6)
C1—N1—C2—C3	2.65 (4)	H4—C4—C5—H5	−30.8 (8)
C1—C8—C7—C6	178.61 (4)	C7—O3—C4—C5	−49.17 (5)
C1—C8—C7—H7	45.9 (6)	C7—C6—C5—H5	−171.4 (6)
C1—C8—C3—C2	3.20 (4)	H7—C7—C6—C5	−155.9 (7)
C1—C8—C3—C4	116.85 (5)	H7—C7—C6—H6	32.0 (9)
C1—C8—C3—H3	−120.5 (6)	H6—C6—C5—H5	−0.1 (7)
C8—C1—N1—C2	−0.46 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2^i	1.08 (1)	2.55 (1)	3.0906 (4)	110 (1)
N1—H1···O1^ii	1.03 (1)	1.84 (1)	2.8601 (3)	173 (1)
N1—H1···C1^ii	1.03 (1)	2.66 (1)	3.5868 (4)	150 (1)

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

(P1_2)

Crystal data

C10H11NO3	F(000) = 408
Mr = 193.19	Dx = 1.373 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.740 (2) Å	Cell parameters from 3500 reflections
b = 10.989 (2) Å	θ = 3–35°
c = 9.736 (2) Å	T = 100 K
β = 90.75 (3)°	Block, colorless
V = 935.0 (3) Å^3	0.2 × 0.2 × 0.1 mm
Z = 4

Data collection

Bruker ApexII Ultra diffractometer	Rint = 0.037
Radiation source: rotating anode	θmax = 51.2°, θmin = 2.8°
180912 measured reflections	h = −19→19
9849 independent reflections	k = 0→23
9298 reflections with I > 2.0σ(I)	l = 0→21

Refinement

Refinement on F^2	22 restraints
Least-squares matrix: full	Primary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.017	Secondary atom site location: difference Fourier map
wR(F^2) = 0.040	Hydrogen site location: difference Fourier map
S = 1.77	All H-atom parameters refined
9849 reflections	Weighting scheme based on measured s.u.'s
171 parameters	(Δ/σ)max = −0.002

Special details

Refinement. Refinement of F² against reflections. The threshold expression of F² > 2sigma(F²) is used for calculating R-factors(gt) 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
O1	0.422915 (16)	0.160750 (12)	0.609425 (16)	0.014678 (10)
O2	0.637245 (16)	0.469960 (11)	0.355803 (14)	0.013093 (9)
O3	0.839040 (14)	0.194663 (11)	0.532867 (12)	0.010116 (8)
N1	0.514792 (16)	0.333568 (12)	0.500645 (15)	0.011031 (9)
H1	0.4543 (5)	0.3981 (3)	0.5539 (5)	0.0175 (3)*
C4	0.862822 (16)	0.235625 (12)	0.391320 (14)	0.009062 (9)
C5	0.917984 (19)	0.117975 (14)	0.321001 (17)	0.011854 (10)
H5	0.9853 (5)	0.1159 (4)	0.2285 (3)	0.0154 (3)*
C6	0.84988 (2)	0.025543 (14)	0.389088 (18)	0.012926 (11)
H6	0.8460 (6)	−0.07093 (18)	0.3674 (5)	0.0166 (3)*
C7	0.751748 (18)	0.085999 (13)	0.500023 (16)	0.010785 (10)
H7	0.7216 (5)	0.0342 (4)	0.5922 (3)	0.0137 (2)*
C1	0.503756 (17)	0.207949 (13)	0.521753 (16)	0.010221 (9)
C2	0.614717 (17)	0.364931 (13)	0.395339 (15)	0.009650 (9)
C3	0.690904 (17)	0.249618 (12)	0.341062 (14)	0.009051 (9)
H3	0.6862 (5)	0.2462 (4)	0.22829 (18)	0.0114 (2)*
C8	0.611772 (17)	0.144003 (13)	0.421076 (16)	0.009946 (9)
H8	0.5505 (5)	0.0750 (3)	0.3601 (4)	0.0126 (2)*
C9	0.964170 (19)	0.347897 (15)	0.383506 (18)	0.012578 (10)
H9B	0.9575 (6)	0.3831 (4)	0.2789 (2)	0.0163 (3)*
H9A	0.9173 (5)	0.4186 (3)	0.4499 (4)	0.0161 (3)*
C10	1.13127 (2)	0.32278 (2)	0.42342 (3)	0.018876 (14)
H10C	1.1844 (6)	0.2599 (4)	0.3535 (4)	0.0253 (4)*
H10B	1.2003 (5)	0.4039 (3)	0.4181 (6)	0.0248 (4)*
H10A	1.1431 (6)	0.2894 (5)	0.5269 (3)	0.0246 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.01282 (4)	0.01214 (4)	0.01922 (5)	−0.00092 (3)	0.00576 (4)	0.00177 (3)
O2	0.01572 (5)	0.00808 (3)	0.01557 (4)	0.00165 (3)	0.00387 (4)	0.00138 (3)
O3	0.01043 (4)	0.01095 (4)	0.00896 (3)	0.00098 (3)	−0.00011 (3)	0.00033 (3)
N1	0.01077 (4)	0.00854 (4)	0.01386 (4)	0.00116 (3)	0.00316 (3)	0.00000 (3)
C4	0.00921 (4)	0.00840 (4)	0.00960 (4)	0.00036 (3)	0.00098 (3)	0.00006 (3)
C5	0.01272 (5)	0.00991 (4)	0.01304 (5)	0.00173 (4)	0.00378 (4)	−0.00051 (3)
C6	0.01368 (5)	0.00837 (4)	0.01683 (5)	0.00204 (4)	0.00405 (4)	−0.00009 (4)
C7	0.01147 (5)	0.00873 (4)	0.01222 (5)	0.00151 (3)	0.00220 (4)	0.00180 (3)
C1	0.00857 (4)	0.00902 (4)	0.01311 (5)	−0.00031 (3)	0.00145 (3)	0.00020 (3)
C2	0.01019 (4)	0.00778 (4)	0.01100 (4)	0.00089 (3)	0.00071 (3)	0.00033 (3)
C3	0.01004 (4)	0.00824 (4)	0.00887 (4)	0.00070 (3)	0.00012 (3)	−0.00031 (3)
C8	0.00982 (4)	0.00801 (4)	0.01202 (4)	−0.00031 (3)	0.00064 (3)	−0.00096 (3)
C9	0.01039 (5)	0.01067 (4)	0.01668 (5)	−0.00140 (3)	0.00042 (4)	0.00095 (4)
C10	0.01103 (5)	0.01900 (7)	0.02653 (8)	−0.00115 (5)	−0.00213 (5)	−0.00005 (6)

Geometric parameters (Å, º)

O1—C1	1.2299 (2)	C7—C8	1.5714 (2)
O2—C2	1.2333 (2)	C7—H7	1.0979 (18)
O3—C4	1.4671 (2)	C1—C8	1.5395 (2)
O3—C7	1.4505 (2)	C2—C3	1.5289 (2)
N1—C2	1.3986 (2)	C3—C8	1.5641 (2)
N1—C1	1.3992 (2)	C3—H3	1.0989 (17)
N1—H1	1.0288 (18)	C8—H8	1.0982 (18)
C4—C3	1.5816 (2)	C9—C10	1.5314 (3)
C4—C9	1.5213 (2)	C9—H9B	1.0907 (18)
C4—C5	1.5431 (2)	C9—H9A	1.0936 (18)
C5—C6	1.3549 (2)	C10—H10A	1.0758 (18)
C5—H5	1.0828 (18)	C10—H10B	1.0782 (18)
C6—C7	1.5388 (2)	C10—H10C	1.0789 (18)
C6—H6	1.0814 (18)
C4—O3—C7	97.243 (10)	O2—C2—C3	126.564 (11)
C2—N1—C1	113.310 (11)	N1—C2—C3	109.153 (11)
C2—N1—H1	122.0 (2)	C2—C3—C4	112.951 (11)
C1—N1—H1	124.7 (2)	C2—C3—C8	104.207 (10)
O3—C4—C3	100.063 (10)	C2—C3—H3	111.3 (2)
O3—C4—C9	112.677 (11)	C4—C3—C8	101.435 (11)
O3—C4—C5	102.041 (11)	C4—C3—H3	109.2 (2)
C3—C4—C9	117.200 (11)	C8—C3—H3	117.5 (2)
C3—C4—C5	104.197 (11)	C1—C8—C7	110.715 (11)
C9—C4—C5	118.149 (11)	C1—C8—C3	104.908 (11)
C4—C5—C6	105.618 (12)	C1—C8—H8	111.1 (2)
C4—C5—H5	124.3 (2)	C7—C8—C3	101.427 (11)
C6—C5—H5	129.7 (2)	C7—C8—H8	110.8 (2)
C7—C6—C5	105.796 (12)	C3—C8—H8	117.3 (2)
C7—C6—H6	123.0 (2)	C4—C9—C10	113.274 (13)
C5—C6—H6	130.7 (2)	C4—C9—H9B	108.1 (2)
O3—C7—C8	100.241 (11)	C4—C9—H9A	108.9 (2)
O3—C7—C6	102.344 (11)	C10—C9—H9B	109.9 (2)
O3—C7—H7	112.2 (2)	C10—C9—H9A	110.0 (2)
C8—C7—C6	105.625 (12)	H9B—C9—H9A	106.5 (3)
C8—C7—H7	114.6 (2)	C9—C10—H10A	112.2 (3)
C6—C7—H7	119.5 (2)	C9—C10—H10B	111.8 (3)
O1—C1—N1	124.011 (12)	C9—C10—H10C	111.8 (3)
O1—C1—C8	127.737 (12)	H10A—C10—H10B	106.3 (4)
N1—C1—C8	108.227 (11)	H10A—C10—H10C	109.6 (4)
O2—C2—N1	124.276 (12)	H10B—C10—H10C	104.7 (4)
O1—C1—N1—C2	179.72 (2)	C5—C4—C3—C8	71.18 (2)
O1—C1—N1—H1	−2.0 (5)	C5—C4—C3—H3	−53.5 (5)
O1—C1—C8—C7	−68.06 (3)	C5—C4—C9—C10	−49.39 (3)
O1—C1—C8—C3	−176.72 (2)	C5—C4—C9—H9B	72.6 (5)
O1—C1—C8—H8	55.6 (5)	C5—C4—C9—H9A	−172.1 (3)
O2—C2—N1—C1	177.07 (2)	C5—C6—C7—C8	72.90 (3)
O2—C2—N1—H1	−1.3 (5)	C5—C6—C7—H7	−156.2 (6)
O2—C2—C3—C4	74.34 (2)	H5—C5—C4—C3	99.4 (5)
O2—C2—C3—C8	−176.43 (2)	H5—C5—C4—C9	−32.7 (5)
O2—C2—C3—H3	−48.9 (5)	H5—C5—C6—C7	−171.9 (5)
O3—C4—C3—C2	76.85 (2)	H5—C5—C6—H6	−0.4 (5)
O3—C4—C3—C8	−34.10 (3)	C6—C7—C8—C1	180.00 (2)
O3—C4—C3—H3	−158.8 (6)	C6—C7—C8—C3	−69.10 (2)
O3—C4—C9—C10	69.30 (3)	C6—C7—C8—H8	56.2 (5)
O3—C4—C9—H9B	−169 (1)	C6—C5—C4—C3	−73.61 (3)
O3—C4—C9—H9A	−53.4 (5)	C6—C5—C4—C9	154.31 (6)
O3—C4—C5—C6	30.17 (4)	H6—C6—C7—C8	−99.5 (5)
O3—C4—C5—H5	−156.8 (6)	H6—C6—C7—H7	31.4 (7)
O3—C7—C8—C1	−73.99 (2)	C7—O3—C4—C3	58.87 (2)
O3—C7—C8—C3	36.93 (3)	C7—O3—C4—C9	−175.87 (2)
O3—C7—C8—H8	162.2 (7)	C7—C8—C3—C2	−118.84 (3)
O3—C7—C6—C5	−31.59 (4)	C7—C8—C3—H3	117.6 (5)
O3—C7—C6—H6	156.0 (6)	H7—C7—C8—C1	46.4 (5)
N1—C2—C3—C4	−104.73 (2)	H7—C7—C8—C3	157.3 (6)
N1—C2—C3—C8	4.50 (2)	H7—C7—C8—H8	−77.4 (7)
N1—C2—C3—H3	132.0 (5)	C1—N1—C2—C3	−3.84 (2)
N1—C1—C8—C7	110.19 (2)	C1—C8—C3—C2	−3.55 (2)
N1—C1—C8—C3	1.54 (2)	C1—C8—C3—H3	−127.2 (5)
N1—C1—C8—H8	−126.2 (5)	C2—N1—C1—C8	1.38 (2)
H1—N1—C2—C3	177.8 (3)	C2—C3—C4—C9	−45.25 (2)
H1—N1—C1—C8	179.7 (4)	C2—C3—C8—H8	120.3 (5)
C4—O3—C7—C8	−60.05 (2)	C3—C4—C9—C10	−175.38 (2)
C4—O3—C7—C6	48.60 (3)	C3—C4—C9—H9B	−53.4 (5)
C4—O3—C7—H7	177.9 (4)	C3—C4—C9—H9A	61.9 (5)
C4—C3—C8—C1	113.94 (2)	H3—C3—C4—C9	79.1 (5)
C4—C3—C8—C7	−1.35 (2)	H3—C3—C8—H8	−3.3 (6)
C4—C3—C8—H8	−122.2 (5)	C8—C3—C4—C9	−156.20 (5)
C4—C9—C10—H10A	−60.1 (6)	H9B—C9—C10—H10A	178.9 (7)
C4—C9—C10—H10B	−179.36 (6)	H9B—C9—C10—H10B	59.6 (8)
C4—C9—C10—H10C	63.6 (6)	H9B—C9—C10—H10C	−57.4 (8)
C4—C5—C6—C7	0.57 (2)	H9A—C9—C10—H10A	62.0 (8)
C4—C5—C6—H6	172.2 (5)	H9A—C9—C10—H10B	−57.3 (8)
C5—C4—O3—C7	−48.14 (3)	H9A—C9—C10—H10C	−174.3 (7)
C5—C4—C3—C2	−177.87 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3^i	1.10 (1)	2.43 (1)	3.3401 (2)	140 (1)
C3—H3···C1^i	1.10 (1)	2.60 (1)	3.5248 (2)	141 (1)
C6—H6···O1^ii	1.08 (1)	2.56 (1)	3.1427 (2)	113 (1)
C8—H8···O1^ii	1.10 (1)	2.62 (1)	3.3754 (2)	125 (1)
N1—H1···O2^iii	1.03 (1)	1.88 (1)	2.9033 (2)	173 (1)

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

(P5_4)

Crystal data

C20H22N2O6	Z = 2
Mr = 386.38	F(000) = 408
Triclinic, P1	Dx = 1.388 Mg m^−3
a = 7.8898 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.5729 (6) Å	Cell parameters from 10000 reflections
c = 14.2922 (11) Å	θ = 3.4–27.9°
α = 88.333 (6)°	µ = 0.10 mm^−1
β = 89.646 (7)°	T = 100 K
γ = 73.099 (7)°	Block, colorless
V = 924.56 (12) Å^3	0.3 × 0.1 × 0.1 mm

Data collection

KUMA4 CCD diffractometer	3534 reflections with I > 2.0σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 28.7°, θmin = 3.4°
Absorption correction: multi-scan CrysAlis	h = −10→10
Tmin = 0.988, Tmax = 0.990	k = −11→11
20070 measured reflections	l = 0→18
4123 independent reflections

Refinement

Refinement on F^2	42 restraints
Least-squares matrix: full	Primary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.030	Secondary atom site location: difference Fourier map
wR(F^2) = 0.062	Hydrogen site location: difference Fourier map
S = 1.33	All H-atom parameters refined
4123 reflections	Weighting scheme based on measured s.u.'s
341 parameters	(Δ/σ)max = −0.001

Special details

Refinement. Refinement of F² against reflections. The threshold expression of F² > 2sigma(F²) is used for calculating R-factors(gt) 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
C1	0.35748 (12)	0.23071 (11)	0.58065 (6)	0.01283 (12)
C2	0.47323 (12)	0.33965 (11)	0.45548 (6)	0.01331 (12)
C3	0.28335 (12)	0.36117 (11)	0.42828 (6)	0.01300 (12)
H3	0.2186 (11)	0.4894 (3)	0.4084 (6)	0.0153 (2)*
C4	0.26999 (13)	0.24136 (11)	0.34904 (6)	0.01459 (13)
C5	0.07088 (13)	0.28271 (12)	0.32902 (7)	0.01926 (14)
C6	0.00321 (13)	0.22101 (12)	0.40224 (7)	0.01952 (14)
H6	−0.1342 (4)	0.2388 (12)	0.4204 (6)	0.0244 (3)*
C7	0.15772 (12)	0.14510 (12)	0.46688 (6)	0.01422 (13)
H7	0.1479 (12)	0.0506 (7)	0.5184 (4)	0.0176 (2)*
C8	0.20498 (12)	0.29074 (11)	0.51263 (6)	0.01287 (12)
H8	0.0897 (7)	0.3717 (9)	0.5477 (5)	0.0152 (2)*
C9	0.39413 (15)	0.22666 (13)	0.26769 (7)	0.02162 (16)
H9A	0.5301 (4)	0.1799 (12)	0.2900 (6)	0.0273 (4)*
H9B	0.3737 (13)	0.3453 (5)	0.2348 (5)	0.0274 (4)*
H9C	0.3674 (11)	0.1463 (8)	0.2170 (4)	0.0274 (4)*
C10	−0.01876 (16)	0.38706 (15)	0.24823 (8)	0.03308 (18)
H10A	−0.1593 (3)	0.4043 (13)	0.2522 (8)	0.0414 (5)*
H10B	0.0337 (13)	0.3341 (11)	0.1829 (4)	0.0414 (5)*
H10C	0.0078 (12)	0.5035 (5)	0.2458 (8)	0.0414 (5)*
N1	0.50670 (10)	0.25471 (10)	0.54073 (5)	0.01411 (11)
H1	0.6299 (5)	0.2259 (13)	0.5717 (6)	0.0212 (3)*
O1	0.35153 (8)	0.17137 (8)	0.65866 (4)	0.01658 (10)
O2	0.58150 (8)	0.38688 (8)	0.41203 (4)	0.01844 (10)
O3	0.30213 (8)	0.09184 (7)	0.40328 (4)	0.01404 (9)
C1A	−0.12300 (12)	0.17711 (11)	0.70205 (6)	0.01251 (12)
C2A	0.02013 (12)	0.11047 (11)	0.84417 (6)	0.01540 (13)
C3A	−0.17219 (12)	0.12372 (11)	0.86515 (6)	0.01354 (13)
H3A	−0.1796 (12)	0.0136 (6)	0.9042 (5)	0.0161 (2)*
C4A	−0.26870 (12)	0.28223 (11)	0.91943 (6)	0.01482 (13)
C5A	−0.45515 (13)	0.26901 (11)	0.93675 (6)	0.01647 (13)
C6A	−0.53669 (13)	0.29981 (12)	0.85376 (7)	0.01679 (13)
H6A	−0.6652 (5)	0.2915 (11)	0.8327 (6)	0.0196 (3)*
C7A	−0.40190 (12)	0.33049 (11)	0.78584 (6)	0.01384 (13)
H7A	−0.4492 (11)	0.4029 (9)	0.7216 (3)	0.0160 (2)*
C8A	−0.26551 (12)	0.16100 (11)	0.76919 (6)	0.01305 (13)
H8A	−0.3311 (9)	0.0748 (7)	0.7419 (6)	0.0159 (2)*
C9A	−0.17284 (15)	0.32682 (13)	0.99985 (7)	0.02230 (15)
H9AA	−0.0519 (6)	0.3503 (10)	0.9774 (6)	0.0266 (3)*
H9AB	−0.1447 (13)	0.2298 (7)	1.0522 (4)	0.0266 (3)*
H9AC	−0.2545 (10)	0.4351 (6)	1.0318 (6)	0.0267 (3)*
C10A	−0.51836 (15)	0.22050 (14)	1.02819 (7)	0.02350 (16)
H10D	−0.6461 (5)	0.2000 (10)	1.0216 (7)	0.0275 (4)*
H10E	−0.5230 (13)	0.3121 (7)	1.0789 (4)	0.0275 (4)*
H10F	−0.4295 (10)	0.1072 (6)	1.0543 (6)	0.0274 (4)*
N1A	0.03517 (11)	0.14507 (10)	0.74919 (5)	0.01510 (11)
H1A	0.1510 (18)	0.1488 (15)	0.7176 (9)	0.029 (3)*
O1A	−0.14257 (8)	0.21573 (8)	0.61909 (4)	0.01546 (9)
O2A	0.14261 (9)	0.07737 (9)	0.89834 (5)	0.02312 (10)
O3A	−0.29824 (8)	0.40196 (7)	0.84372 (4)	0.01480 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0114 (5)	0.0149 (5)	0.0119 (5)	−0.0036 (4)	0.0010 (4)	0.0001 (4)
C2	0.0127 (5)	0.0149 (5)	0.0121 (4)	−0.0038 (4)	0.0008 (4)	0.0007 (4)
C3	0.0141 (5)	0.0112 (5)	0.0129 (5)	−0.0024 (4)	−0.0007 (4)	0.0003 (4)
C4	0.0205 (5)	0.0127 (5)	0.0113 (4)	−0.0061 (4)	−0.0006 (4)	0.0010 (4)
C5	0.0200 (5)	0.0207 (5)	0.0179 (5)	−0.0075 (4)	−0.0076 (4)	0.0033 (4)
C6	0.0179 (5)	0.0248 (5)	0.0180 (5)	−0.0096 (5)	−0.0034 (4)	0.0004 (4)
C7	0.0145 (5)	0.0154 (5)	0.0138 (5)	−0.0059 (4)	0.0007 (4)	−0.0005 (4)
C8	0.0116 (5)	0.0135 (5)	0.0126 (5)	−0.0023 (4)	0.0003 (4)	−0.0005 (4)
C9	0.0350 (6)	0.0198 (5)	0.0130 (5)	−0.0128 (5)	0.0060 (4)	−0.0002 (4)
C10	0.0384 (7)	0.0347 (7)	0.0287 (6)	−0.0156 (6)	−0.0181 (5)	0.0127 (5)
N1	0.0114 (4)	0.0180 (4)	0.0129 (4)	−0.0045 (3)	−0.0001 (3)	0.0024 (3)
O1	0.0129 (3)	0.0254 (4)	0.0112 (3)	−0.0055 (3)	0.0003 (3)	0.0032 (3)
O2	0.0154 (4)	0.0234 (4)	0.0172 (4)	−0.0074 (3)	0.0015 (3)	0.0048 (3)
O3	0.0189 (3)	0.0111 (3)	0.0123 (3)	−0.0046 (3)	0.0024 (3)	−0.0005 (2)
C1A	0.0116 (5)	0.0141 (5)	0.0119 (5)	−0.0041 (4)	0.0012 (4)	−0.0003 (4)
C2A	0.0150 (5)	0.0170 (5)	0.0130 (5)	−0.0031 (4)	−0.0009 (4)	0.0027 (4)
C3A	0.0160 (5)	0.0129 (5)	0.0113 (4)	−0.0038 (4)	0.0008 (4)	0.0020 (4)
C4A	0.0189 (5)	0.0128 (5)	0.0114 (4)	−0.0026 (4)	−0.0001 (4)	0.0006 (4)
C5A	0.0176 (5)	0.0178 (5)	0.0118 (5)	−0.0015 (4)	0.0036 (4)	−0.0007 (4)
C6A	0.0144 (5)	0.0210 (5)	0.0131 (5)	−0.0025 (4)	0.0010 (4)	0.0006 (4)
C7A	0.0142 (5)	0.0142 (5)	0.0116 (4)	−0.0017 (4)	0.0003 (4)	0.0000 (4)
C8A	0.0145 (5)	0.0127 (5)	0.0122 (5)	−0.0046 (4)	0.0009 (4)	0.0003 (4)
C9A	0.0270 (6)	0.0225 (6)	0.0165 (5)	−0.0054 (5)	−0.0036 (4)	−0.0033 (4)
C10A	0.0264 (6)	0.0262 (6)	0.0152 (5)	−0.0038 (5)	0.0049 (4)	0.0016 (4)
N1A	0.0125 (4)	0.0197 (4)	0.0128 (4)	−0.0044 (3)	−0.0002 (3)	0.0019 (3)
O1A	0.0141 (3)	0.0215 (4)	0.0115 (3)	−0.0064 (3)	0.0006 (3)	0.0017 (3)
O2A	0.0163 (4)	0.0335 (4)	0.0176 (4)	−0.0048 (3)	−0.0041 (3)	0.0063 (3)
O3A	0.0184 (4)	0.0110 (3)	0.0149 (3)	−0.0041 (3)	−0.0003 (3)	−0.0003 (3)

Geometric parameters (Å, º)

C1—O1	1.2183 (11)	C1A—O1A	1.2203 (11)
C1—N1	1.3710 (11)	C1A—N1A	1.3737 (11)
C1—C8	1.5109 (12)	C1A—C8A	1.5078 (12)
C2—O2	1.2080 (11)	C2A—O2A	1.2045 (11)
C2—N1	1.3874 (11)	C2A—N1A	1.3929 (12)
C2—C3	1.5072 (12)	C2A—C3A	1.5170 (13)
C3—C4	1.5751 (12)	C3A—C4A	1.5749 (13)
C3—C8	1.5381 (12)	C3A—C8A	1.5412 (12)
C3—H3	1.0990 (13)	C3A—H3A	1.0988 (13)
C4—O3	1.4366 (11)	C4A—O3A	1.4416 (11)
C4—C5	1.5334 (13)	C4A—C5A	1.5261 (13)
C4—C9	1.4998 (14)	C4A—C9A	1.4979 (13)
C5—C6	1.3361 (14)	C5A—C6A	1.3352 (13)
C5—C10	1.4886 (14)	C5A—C10A	1.4868 (13)
C6—C7	1.5102 (13)	C6A—C7A	1.5092 (13)
C6—H6	1.0812 (13)	C6A—H6A	1.0816 (13)
C7—O3	1.4288 (11)	C7A—O3A	1.4345 (10)
C7—C8	1.5642 (12)	C7A—C8A	1.5601 (13)
C7—H7	1.0980 (13)	C7A—H7A	1.0974 (13)
C8—H8	1.0990 (13)	C8A—H8A	1.0988 (13)
C9—H9B	1.0768 (13)	C9A—H9AA	1.0765 (13)
C9—H9C	1.0768 (13)	C9A—H9AC	1.0765 (13)
C9—H9A	1.0770 (13)	C9A—H9AB	1.0767 (13)
C10—H10A	1.0768 (13)	C10A—H10E	1.0769 (13)
C10—H10B	1.0768 (13)	C10A—H10F	1.0770 (13)
C10—H10C	1.0771 (13)	C10A—H10D	1.0773 (13)
N1—H1	1.0304 (13)	N1A—H1A	1.025 (13)
O1—C1—N1	124.65 (7)	O1A—C1A—N1A	124.26 (7)
O1—C1—C8	126.51 (7)	O1A—C1A—C8A	126.35 (7)
N1—C1—C8	108.84 (7)	N1A—C1A—C8A	109.37 (7)
O2—C2—N1	124.23 (7)	O2A—C2A—N1A	123.93 (7)
O2—C2—C3	127.10 (7)	O2A—C2A—C3A	127.60 (7)
N1—C2—C3	108.67 (7)	N1A—C2A—C3A	108.47 (7)
C2—C3—C4	111.41 (7)	C2A—C3A—C4A	112.74 (7)
C2—C3—C8	104.48 (7)	C2A—C3A—C8A	104.54 (7)
C2—C3—H3	109.9 (4)	C2A—C3A—H3A	109.3 (4)
C4—C3—C8	101.66 (7)	C4A—C3A—C8A	101.28 (7)
C4—C3—H3	112.4 (4)	C4A—C3A—H3A	111.0 (4)
C8—C3—H3	116.6 (4)	C8A—C3A—H3A	117.7 (4)
O3—C4—C3	99.98 (6)	O3A—C4A—C3A	100.09 (6)
O3—C4—C5	101.85 (7)	O3A—C4A—C5A	101.86 (7)
O3—C4—C9	112.44 (7)	O3A—C4A—C9A	112.10 (7)
C3—C4—C5	104.18 (7)	C3A—C4A—C5A	104.48 (7)
C3—C4—C9	117.40 (7)	C3A—C4A—C9A	117.84 (7)
C5—C4—C9	118.39 (8)	C5A—C4A—C9A	117.91 (7)
C4—C5—C6	105.41 (8)	C4A—C5A—C6A	105.56 (8)
C4—C5—C10	123.82 (8)	C4A—C5A—C10A	124.30 (7)
C6—C5—C10	130.43 (8)	C6A—C5A—C10A	130.03 (8)
C7—C6—C5	105.65 (8)	C7A—C6A—C5A	105.80 (8)
C7—C6—H6	124.6 (4)	C7A—C6A—H6A	123.5 (4)
C5—C6—H6	128.8 (4)	C5A—C6A—H6A	130.3 (4)
O3—C7—C8	100.70 (6)	O3A—C7A—C8A	100.18 (6)
O3—C7—C6	102.68 (7)	O3A—C7A—C6A	102.52 (7)
O3—C7—H7	113.6 (4)	O3A—C7A—H7A	112.9 (4)
C8—C7—C6	105.88 (7)	C8A—C7A—C6A	106.21 (7)
C8—C7—H7	112.7 (4)	C8A—C7A—H7A	114.3 (4)
C6—C7—H7	119.2 (4)	C6A—C7A—H7A	118.6 (4)
C1—C8—C7	111.22 (7)	C1A—C8A—C7A	110.85 (7)
C1—C8—C3	104.71 (7)	C1A—C8A—C3A	104.65 (7)
C1—C8—H8	110.2 (4)	C1A—C8A—H8A	109.5 (4)
C7—C8—C3	100.86 (7)	C7A—C8A—C3A	101.31 (7)
C7—C8—H8	111.5 (4)	C7A—C8A—H8A	111.1 (4)
C3—C8—H8	117.9 (4)	C3A—C8A—H8A	119.0 (4)
C4—C9—H9B	108.8 (5)	C4A—C9A—H9AA	111.4 (5)
C4—C9—H9C	110.2 (4)	C4A—C9A—H9AC	110.3 (5)
C4—C9—H9A	111.2 (5)	C4A—C9A—H9AB	109.5 (4)
H9B—C9—H9C	108.4 (6)	H9AA—C9A—H9AC	108.0 (7)
H9B—C9—H9A	109.3 (7)	H9AA—C9A—H9AB	110.0 (7)
H9C—C9—H9A	108.8 (7)	H9AC—C9A—H9AB	107.6 (6)
C5—C10—H10A	109.6 (6)	C5A—C10A—H10E	110.0 (4)
C5—C10—H10B	110.9 (5)	C5A—C10A—H10F	110.5 (5)
C5—C10—H10C	111.9 (5)	C5A—C10A—H10D	111.5 (5)
H10A—C10—H10B	110.9 (8)	H10E—C10A—H10F	107.9 (6)
H10A—C10—H10C	110.0 (7)	H10E—C10A—H10D	110.6 (7)
H10B—C10—H10C	103.4 (8)	H10F—C10A—H10D	106.2 (7)
C1—N1—C2	112.90 (7)	C1A—N1A—C2A	112.85 (7)
C1—N1—H1	125.5 (4)	C1A—N1A—H1A	123.2 (7)
C2—N1—H1	121.2 (5)	C2A—N1A—H1A	123.9 (7)
C4—O3—C7	97.31 (6)	C4A—O3A—C7A	97.10 (6)
C1—N1—C2—O2	173.20 (13)	C1A—N1A—C2A—O2A	179.25 (12)
C1—N1—C2—C3	−6.78 (13)	C1A—N1A—C2A—C3A	−1.29 (13)
C1—C8—C7—O3	−74.22 (13)	C1A—C8A—C7A—O3A	−73.45 (13)
C1—C8—C7—C6	179.17 (14)	C1A—C8A—C7A—C6A	−179.81 (14)
C1—C8—C7—H7	47.2 (10)	C1A—C8A—C7A—H7A	47.5 (10)
C1—C8—C3—C2	−1.30 (13)	C1A—C8A—C3A—C2A	−3.59 (13)
C1—C8—C3—C4	114.69 (15)	C1A—C8A—C3A—C4A	113.73 (15)
C1—C8—C3—H3	−122.8 (9)	C1A—C8A—C3A—H3A	−125.1 (9)
C2—N1—C1—O1	−173.68 (13)	C2A—N1A—C1A—O1A	177.44 (12)
C2—N1—C1—C8	5.88 (13)	C2A—N1A—C1A—C8A	−1.16 (13)
C2—C3—C4—O3	76.25 (13)	C2A—C3A—C4A—O3A	76.97 (13)
C2—C3—C4—C5	−178.71 (14)	C2A—C3A—C4A—C5A	−177.86 (14)
C2—C3—C4—C9	−45.60 (16)	C2A—C3A—C4A—C9A	−44.77 (16)
C2—C3—C8—C7	−116.85 (15)	C2A—C3A—C8A—C7A	−118.89 (16)
C2—C3—C8—H8	121.6 (9)	C2A—C3A—C8A—H8A	119.0 (8)
C3—C2—N1—H1	179.3 (7)	C3A—C2A—N1A—H1A	177.5 (9)
C3—C4—O3—C7	58.87 (14)	C3A—C4A—O3A—C7A	59.07 (14)
C3—C4—C5—C6	−73.53 (15)	C3A—C4A—C5A—C6A	−73.30 (15)
C3—C4—C5—C10	100.32 (16)	C3A—C4A—C5A—C10A	103.19 (15)
C3—C4—C9—H9B	−58.3 (9)	C3A—C4A—C9A—H9AA	61.7 (10)
C3—C4—C9—H9C	−177.1 (4)	C3A—C4A—C9A—H9AC	−178.4 (4)
C3—C4—C9—H9A	62 (1)	C3A—C4A—C9A—H9AB	−60.2 (9)
C3—C8—C1—O1	177.03 (12)	C3A—C8A—C1A—O1A	−175.54 (12)
C3—C8—C1—N1	−2.53 (13)	C3A—C8A—C1A—N1A	3.02 (13)
C3—C8—C7—O3	36.38 (19)	C3A—C8A—C7A—O3A	37.17 (18)
C3—C8—C7—C6	−70.23 (14)	C3A—C8A—C7A—C6A	−69.19 (14)
C3—C8—C7—H7	157.8 (10)	C3A—C8A—C7A—H7A	158 (1)
H3—C3—C2—O2	−49.5 (10)	H3A—C3A—C2A—O2A	−50.6 (9)
H3—C3—C2—N1	130.5 (10)	H3A—C3A—C2A—N1A	130.0 (9)
H3—C3—C4—O3	−160 (1)	H3A—C3A—C4A—O3A	−160.0 (10)
H3—C3—C4—C5	−54.9 (10)	H3A—C3A—C4A—C5A	−54.8 (9)
H3—C3—C4—C9	78.2 (10)	H3A—C3A—C4A—C9A	78.3 (9)
H3—C3—C8—C7	121.7 (9)	H3A—C3A—C8A—C7A	119.6 (9)
H3—C3—C8—H8	0 (1)	H3A—C3A—C8A—H8A	−2 (1)
C4—O3—C7—C8	−60.09 (14)	C4A—O3A—C7A—C8A	−60.47 (15)
C4—O3—C7—C6	49.05 (17)	C4A—O3A—C7A—C6A	48.83 (17)
C4—O3—C7—H7	179.2 (7)	C4A—O3A—C7A—H7A	177.6 (8)
C4—C3—C2—O2	75.72 (14)	C4A—C3A—C2A—O2A	73.38 (15)
C4—C3—C2—N1	−104.30 (14)	C4A—C3A—C2A—N1A	−106.05 (14)
C4—C3—C8—C7	−0.86 (13)	C4A—C3A—C8A—C7A	−1.58 (13)
C4—C3—C8—H8	−122.4 (9)	C4A—C3A—C8A—H8A	−123.7 (8)
C4—C5—C6—C7	0.79 (14)	C4A—C5A—C6A—C7A	0.39 (13)
C4—C5—C6—H6	170.1 (9)	C4A—C5A—C6A—H6A	173.1 (9)
C4—C5—C10—H10A	−176.2 (8)	C4A—C5A—C10A—H10E	66 (1)
C4—C5—C10—H10B	61 (1)	C4A—C5A—C10A—H10F	−53 (1)
C4—C5—C10—H10C	−53.9 (10)	C4A—C5A—C10A—H10D	−170.6 (8)
C5—C4—O3—C7	−48.05 (18)	C5A—C4A—O3A—C7A	−48.21 (17)
C5—C4—C3—C8	70.49 (14)	C5A—C4A—C3A—C8A	70.97 (14)
C5—C4—C9—H9B	68 (1)	C5A—C4A—C9A—H9AA	−171.4 (5)
C5—C4—C9—H9C	−50.7 (10)	C5A—C4A—C9A—H9AC	−52 (1)
C5—C4—C9—H9A	−171.4 (6)	C5A—C4A—C9A—H9AB	67 (1)
C5—C6—C7—O3	−31.8 (2)	C5A—C6A—C7A—O3A	−31.5 (2)
C5—C6—C7—C8	73.42 (15)	C5A—C6A—C7A—C8A	73.19 (15)
C5—C6—C7—H7	−158.4 (10)	C5A—C6A—C7A—H7A	−157 (1)
C6—C7—C8—H8	55.7 (9)	C6A—C7A—C8A—H8A	58.2 (9)
C6—C5—C4—O3	30.1 (2)	C6A—C5A—C4A—O3A	30.5 (2)
C6—C5—C4—C9	153.9 (3)	C6A—C5A—C4A—C9A	153.6 (3)
C6—C5—C10—H10A	−4 (1)	C6A—C5A—C10A—H10E	−118.0 (9)
C6—C5—C10—H10B	−127 (1)	C6A—C5A—C10A—H10F	123 (1)
C6—C5—C10—H10C	118 (1)	C6A—C5A—C10A—H10D	5 (1)
H6—C6—C7—O3	158 (1)	H6A—C6A—C7A—O3A	155.2 (10)
H6—C6—C7—C8	−96 (1)	H6A—C6A—C7A—C8A	−100.1 (9)
H6—C6—C7—H7	32 (1)	H6A—C6A—C7A—H7A	30 (1)
H6—C6—C5—C10	−3.2 (9)	H6A—C6A—C5A—C10A	−3.2 (9)
C7—O3—C4—C9	−175.81 (14)	C7A—O3A—C4A—C9A	−175.18 (14)
C7—C8—C1—O1	−74.86 (14)	C7A—C8A—C1A—O1A	−67.08 (14)
C7—C8—C1—N1	105.59 (14)	C7A—C8A—C1A—N1A	111.48 (15)
C7—C6—C5—C10	−172.49 (16)	C7A—C6A—C5A—C10A	−175.82 (15)
H7—C7—C8—H8	−76 (1)	H7A—C7A—C8A—H8A	−74 (1)
C8—C1—N1—H1	179.5 (8)	C8A—C1A—N1A—H1A	−180.0 (9)
C8—C3—C2—O2	−175.29 (12)	C8A—C3A—C2A—O2A	−177.48 (13)
C8—C3—C2—N1	4.69 (13)	C8A—C3A—C2A—N1A	3.08 (13)
C8—C3—C4—O3	−34.6 (2)	C8A—C3A—C4A—O3A	−34.2 (2)
C8—C3—C4—C9	−156.4 (3)	C8A—C3A—C4A—C9A	−155.9 (3)
H8—C8—C1—O1	49.3 (9)	H8A—C8A—C1A—O1A	55.8 (9)
H8—C8—C1—N1	−130.2 (9)	H8A—C8A—C1A—N1A	−125.6 (8)
H8—C8—C7—O3	162 (1)	H8A—C8A—C7A—O3A	164.6 (10)
C9—C4—C5—C10	−32.22 (18)	C9A—C4A—C5A—C10A	−29.87 (16)
H9A—C9—C4—O3	−53 (1)	H9AA—C9A—C4A—O3A	−53.6 (9)
H9B—C9—C4—O3	−173.5 (4)	H9AB—C9A—C4A—O3A	−175.6 (3)
H9C—C9—C4—O3	67.7 (9)	H9AC—C9A—C4A—O3A	66.2 (10)
C10—C5—C4—O3	−156.1 (3)	C10A—C5A—C4A—O3A	−153.0 (2)
H1—N1—C1—O1	−0.1 (10)	H1A—N1A—C1A—O1A	−1 (1)
H1—N1—C2—O2	−1 (1)	H1A—N1A—C2A—O2A	−2 (1)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2^i	1.08 (1)	2.24 (1)	3.2198 (12)	150 (1)
N1A—H1A···O1	1.02 (1)	1.84 (1)	2.8680 (10)	176 (1)
C8A—H8A···O3^ii	1.10 (1)	2.53 (1)	3.3973 (11)	136 (1)
C10A—H10F···O2A^iii	1.08 (1)	2.44 (1)	3.4486 (13)	155 (1)
C3—H3···O1A^iv	1.10 (1)	2.44 (1)	3.5175 (11)	166 (1)
C9—H9B···O3A^iv	1.08 (1)	2.33 (1)	3.4006 (12)	173 (1)
N1—H1···O1A^v	1.03 (1)	1.90 (1)	2.9159 (9)	168 (1)

Symmetry codes: (i) x−1, y, z; (ii) −x, −y, −z+1; (iii) −x, −y, −z+2; (iv) −x, −y+1, −z+1; (v) x+1, y, z.

(P9_5)

Crystal data

C18H18N2O8	F(000) = 816
Mr = 390.33	Dx = 1.549 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.6065 (4) Å	Cell parameters from 3424 reflections
b = 7.3059 (3) Å	θ = 2.2–29.2°
c = 20.0511 (8) Å	µ = 0.12 mm^−1
β = 99.977 (4)°	T = 100 K
V = 1674.55 (12) Å^3	Block, colorless
Z = 4	0.3 × 0.2 × 0.1 mm

Data collection

SuperNova, Single source at offset, Eos diffractometer	2994 reflections with I > 2.0σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Detector resolution: 16.0026 pixels mm^-1	θmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan CrysAlisPro 1.171.38.43c (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −15→14
Tmin = 0.647, Tmax = 1.000	k = 0→9
9481 measured reflections	l = 0→26
3787 independent reflections

Refinement

Refinement on F^2	36 restraints
Least-squares matrix: full	Primary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.036	Secondary atom site location: difference Fourier map
wR(F^2) = 0.242	Hydrogen site location: difference Fourier map
S = 1.87	All H-atom parameters refined
3786 reflections	Weighting scheme based on measured s.u.'s
325 parameters	(Δ/σ)max = −0.001

Special details

Refinement. Refinement of F² against reflections. The threshold expression of F² > 2sigma(F²) is used for calculating R-factors(gt) 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
O3	0.59672 (8)	0.55483 (16)	0.38585 (5)	0.00917 (14)
O2A	0.69046 (8)	0.40865 (16)	0.52946 (5)	0.01110 (15)
O3A	0.80527 (8)	0.81940 (16)	0.64303 (5)	0.01036 (14)
O4A	0.96586 (8)	0.46812 (16)	0.56478 (5)	0.01269 (14)
O4	0.81961 (8)	0.34628 (17)	0.42738 (5)	0.01211 (15)
H4	0.7808 (7)	0.366 (3)	0.4659 (3)	0.0179 (2)*
O1	0.29555 (8)	0.62535 (17)	0.29486 (5)	0.01607 (16)
O1A	0.50087 (8)	0.92397 (17)	0.57640 (5)	0.01457 (15)
O2	0.52856 (9)	0.14362 (17)	0.26124 (5)	0.01627 (15)
N1A	0.57603 (10)	0.6449 (2)	0.55434 (6)	0.01110 (17)
H1A	0.5090 (6)	0.5679 (13)	0.5673 (6)	0.0170 (2)*
N1	0.39090 (10)	0.3592 (2)	0.27679 (7)	0.01337 (18)
H1	0.3203 (6)	0.2722 (11)	0.2736 (9)	0.0199 (2)*
C2A	0.67620 (12)	0.5718 (2)	0.53717 (7)	0.0094 (2)
C4	0.67142 (11)	0.4835 (2)	0.34126 (7)	0.0086 (2)
C4A	0.86408 (11)	0.7365 (2)	0.59296 (7)	0.00844 (19)
C2	0.50159 (12)	0.3007 (3)	0.26930 (7)	0.0117 (2)
C3	0.58092 (12)	0.4676 (2)	0.27301 (7)	0.0103 (2)
H3	0.6231 (7)	0.467 (2)	0.2280 (3)	0.01239 (15)*
C1A	0.57802 (12)	0.8338 (2)	0.55919 (7)	0.0106 (2)
C7A	0.77008 (12)	0.9848 (2)	0.60591 (8)	0.0117 (2)
H7A	0.7238 (8)	1.0813 (11)	0.6339 (4)	0.01374 (17)*
C5A	0.94113 (12)	0.8927 (2)	0.57614 (8)	0.0129 (2)
H5A	1.0199 (5)	0.866 (2)	0.5557 (5)	0.01532 (18)*
C5	0.74497 (12)	0.6506 (3)	0.33164 (8)	0.0125 (2)
H5	0.8290 (4)	0.638 (2)	0.3156 (5)	0.01514 (18)*
C8A	0.69238 (11)	0.9028 (2)	0.54145 (7)	0.0106 (2)
H8A	0.6733 (12)	1.0002 (10)	0.4992 (3)	0.01258 (15)*
C9	0.73355 (12)	0.3112 (2)	0.36934 (8)	0.0112 (2)
H9A	0.6698 (6)	0.2118 (11)	0.3810 (6)	0.01359 (16)*
H9B	0.7784 (7)	0.2531 (16)	0.3307 (3)	0.01359 (16)*
C3A	0.76068 (12)	0.7264 (2)	0.53040 (7)	0.0097 (2)
H3A	0.7936 (8)	0.713 (2)	0.4824 (3)	0.01166 (14)*
C1	0.38257 (12)	0.5466 (2)	0.28446 (7)	0.0116 (2)
C9A	0.92238 (12)	0.5575 (2)	0.61758 (7)	0.0105 (2)
H9AA	0.9917 (6)	0.583 (2)	0.6607 (3)	0.01242 (15)*
H9AB	0.8610 (6)	0.4670 (12)	0.6369 (5)	0.01242 (15)*
C8	0.50002 (12)	0.6320 (2)	0.27952 (7)	0.0110 (2)
H8	0.4877 (12)	0.7318 (10)	0.2379 (3)	0.01327 (16)*
C7	0.55964 (12)	0.7179 (2)	0.34743 (8)	0.0114 (2)
H7	0.5039 (7)	0.8072 (12)	0.3723 (5)	0.01348 (16)*
C6A	0.88315 (13)	1.0467 (3)	0.58460 (8)	0.0147 (2)
H6A	0.9039 (11)	1.1870 (6)	0.5741 (7)	0.0175 (2)*
C6	0.67533 (13)	0.7954 (2)	0.33522 (8)	0.0155 (2)
H6	0.6889 (12)	0.9398 (5)	0.3274 (8)	0.0184 (2)*
H4A	1.0394 (5)	0.5272 (15)	0.5612 (7)	0.0193 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0084 (4)	0.0108 (6)	0.0083 (5)	0.0000 (5)	0.0012 (4)	−0.0013 (5)
O2A	0.0096 (5)	0.0098 (6)	0.0145 (5)	−0.0013 (5)	0.0036 (4)	−0.0017 (5)
O3A	0.0101 (5)	0.0112 (6)	0.0095 (5)	0.0002 (5)	0.0011 (4)	−0.0010 (5)
O4A	0.0119 (5)	0.0089 (6)	0.0178 (6)	0.0002 (5)	0.0040 (4)	−0.0011 (5)
O4	0.0084 (4)	0.0138 (7)	0.0138 (5)	0.0022 (5)	0.0007 (4)	0.0003 (5)
O1	0.0099 (5)	0.0185 (7)	0.0204 (6)	0.0037 (5)	0.0043 (4)	0.0025 (6)
O1A	0.0105 (5)	0.0146 (7)	0.0192 (6)	0.0022 (5)	0.0042 (4)	−0.0034 (5)
O2	0.0141 (5)	0.0124 (7)	0.0214 (6)	−0.0002 (5)	0.0004 (4)	−0.0063 (6)
N1A	0.0086 (5)	0.0104 (8)	0.0149 (7)	−0.0009 (6)	0.0039 (5)	−0.0015 (7)
N1	0.0083 (5)	0.0146 (8)	0.0168 (7)	−0.0012 (6)	0.0011 (5)	−0.0008 (7)
C2A	0.0078 (6)	0.0112 (9)	0.0094 (7)	0.0005 (7)	0.0022 (5)	−0.0022 (7)
C4	0.0079 (6)	0.0088 (9)	0.0096 (7)	−0.0002 (7)	0.0029 (5)	−0.0020 (7)
C4A	0.0073 (6)	0.0087 (9)	0.0090 (7)	0.0005 (6)	0.0006 (5)	−0.0012 (7)
C2	0.0092 (6)	0.0127 (10)	0.0128 (7)	0.0000 (7)	0.0005 (5)	−0.0028 (7)
C3	0.0099 (6)	0.0105 (9)	0.0105 (7)	−0.0002 (7)	0.0021 (5)	0.0004 (7)
C1A	0.0085 (6)	0.0115 (9)	0.0115 (7)	0.0023 (7)	0.0010 (5)	−0.0005 (7)
C7A	0.0107 (7)	0.0094 (9)	0.0142 (8)	0.0003 (7)	0.0003 (6)	−0.0013 (7)
C5A	0.0085 (6)	0.0098 (9)	0.0199 (8)	−0.0010 (7)	0.0007 (6)	0.0000 (8)
C5	0.0102 (6)	0.0094 (9)	0.0182 (8)	−0.0007 (7)	0.0031 (6)	0.0008 (8)
C8A	0.0101 (6)	0.0093 (9)	0.0120 (8)	0.0007 (7)	0.0006 (6)	0.0009 (7)
C9	0.0090 (6)	0.0087 (9)	0.0162 (8)	0.0017 (7)	0.0028 (6)	0.0007 (7)
C3A	0.0074 (6)	0.0104 (9)	0.0114 (7)	0.0019 (6)	0.0019 (5)	0.0005 (7)
C1	0.0098 (7)	0.0135 (9)	0.0114 (7)	0.0005 (7)	0.0010 (5)	0.0019 (8)
C9A	0.0096 (6)	0.0090 (9)	0.0124 (7)	0.0012 (7)	0.0007 (5)	0.0009 (8)
C8	0.0099 (6)	0.0115 (9)	0.0118 (7)	0.0011 (7)	0.0020 (6)	0.0019 (7)
C7	0.0109 (7)	0.0065 (9)	0.0162 (8)	0.0012 (7)	0.0008 (6)	−0.0009 (7)
C6A	0.0106 (7)	0.0082 (9)	0.0249 (8)	0.0010 (7)	0.0016 (6)	0.0000 (8)
C6	0.0138 (7)	0.0089 (9)	0.0232 (9)	0.0002 (7)	0.0016 (6)	0.0014 (8)

Geometric parameters (Å, º)

O3—C4	1.4460 (17)	C2—C3	1.521 (2)
O3—C7	1.4434 (19)	C3—C8	1.544 (2)
O2A—C2A	1.217 (2)	C3—H3	1.0989 (12)
O3A—C4A	1.4414 (18)	C1A—C8A	1.519 (2)
O3A—C7A	1.4410 (19)	C7A—C8A	1.562 (2)
O4A—C9A	1.4096 (18)	C7A—C6A	1.518 (2)
O4A—H4A	0.9700 (12)	C7A—H7A	1.0979 (12)
O4—C9	1.4194 (17)	C5A—C6A	1.337 (2)
O4—H4	0.9700 (12)	C5A—H5A	1.0819 (12)
O1—C1	1.2116 (18)	C5—C6	1.341 (2)
O1A—C1A	1.2093 (18)	C5—H5	1.0819 (12)
O2—C2	1.208 (2)	C8A—C3A	1.549 (2)
N1A—C2A	1.3764 (18)	C8A—H8A	1.0990 (12)
N1A—C1A	1.383 (2)	C9—H9A	1.0909 (12)
N1A—H1A	1.0299 (12)	C9—H9B	1.0911 (12)
N1—C1	1.383 (2)	C3A—H3A	1.0989 (12)
N1—C2	1.3864 (19)	C1—C8	1.518 (2)
N1—H1	1.0299 (12)	C9A—H9AB	1.0910 (12)
C2A—C3A	1.517 (2)	C9A—H9AA	1.0911 (12)
C4—C9	1.511 (2)	C8—C7	1.549 (2)
C4—C3	1.5784 (19)	C8—H8	1.0989 (12)
C4—C5	1.521 (2)	C7—C6	1.516 (2)
C4A—C9A	1.516 (2)	C7—H7	1.0978 (12)
C4A—C3A	1.5804 (18)	C6A—H6A	1.0818 (12)
C4A—C5A	1.523 (2)	C6—H6	1.0819 (12)
C4—O3—C7	97.04 (11)	C4—C5—H5	121.7 (8)
C4A—O3A—C7A	96.82 (11)	C6—C5—H5	131.7 (7)
C9A—O4A—H4A	106.5 (9)	C1A—C8A—C7A	109.65 (11)
C9—O4—H4	108.8 (6)	C1A—C8A—C3A	104.30 (12)
C2A—N1A—C1A	113.60 (13)	C1A—C8A—H8A	109.2 (7)
C2A—N1A—H1A	124.0 (6)	C7A—C8A—C3A	101.62 (11)
C1A—N1A—H1A	122.1 (6)	C7A—C8A—H8A	113.5 (5)
C1—N1—C2	113.64 (13)	C3A—C8A—H8A	117.9 (6)
C1—N1—H1	123.2 (5)	O4—C9—C4	112.20 (11)
C2—N1—H1	123.0 (5)	O4—C9—H9A	110.6 (6)
O2A—C2A—N1A	123.46 (13)	O4—C9—H9B	107.3 (5)
O2A—C2A—C3A	127.84 (13)	C4—C9—H9A	109.7 (5)
N1A—C2A—C3A	108.69 (12)	C4—C9—H9B	108.3 (6)
O3—C4—C9	111.62 (11)	H9A—C9—H9B	108.5 (9)
O3—C4—C3	100.51 (10)	C2A—C3A—C4A	112.19 (11)
O3—C4—C5	101.49 (11)	C2A—C3A—C8A	104.59 (12)
C9—C4—C3	117.68 (11)	C2A—C3A—H3A	110.0 (8)
C9—C4—C5	118.30 (12)	C4A—C3A—C8A	100.63 (11)
C3—C4—C5	104.67 (11)	C4A—C3A—H3A	111.6 (5)
O3A—C4A—C9A	111.97 (11)	C8A—C3A—H3A	117.5 (7)
O3A—C4A—C3A	100.75 (10)	O1—C1—N1	124.47 (13)
O3A—C4A—C5A	101.93 (11)	O1—C1—C8	126.93 (12)
C9A—C4A—C3A	116.92 (11)	N1—C1—C8	108.58 (13)
C9A—C4A—C5A	118.19 (12)	O4A—C9A—C4A	110.66 (12)
C3A—C4A—C5A	104.70 (11)	O4A—C9A—H9AB	109.1 (6)
O2—C2—N1	125.00 (13)	O4A—C9A—H9AA	111.4 (6)
O2—C2—C3	126.80 (14)	C4A—C9A—H9AB	110.9 (5)
N1—C2—C3	108.19 (12)	C4A—C9A—H9AA	109.5 (8)
C2—C3—C4	114.07 (11)	H9AB—C9A—H9AA	105.2 (8)
C2—C3—C8	104.80 (12)	C1—C8—C7	112.24 (11)
C2—C3—H3	108.1 (8)	C1—C8—C3	104.59 (12)
C4—C3—C8	101.08 (11)	C1—C8—H8	108.8 (7)
C4—C3—H3	112.8 (4)	C7—C8—C3	101.77 (11)
C8—C3—H3	115.8 (8)	C7—C8—H8	112.2 (5)
O1A—C1A—N1A	124.03 (13)	C3—C8—H8	117.0 (6)
O1A—C1A—C8A	127.33 (12)	O3—C7—C8	100.43 (11)
N1A—C1A—C8A	108.62 (12)	O3—C7—C6	101.77 (11)
O3A—C7A—C8A	100.18 (11)	O3—C7—H7	113.1 (5)
O3A—C7A—C6A	102.34 (11)	C8—C7—C6	106.42 (11)
O3A—C7A—H7A	113.2 (5)	C8—C7—H7	115.6 (5)
C8A—C7A—C6A	106.55 (11)	C6—C7—H7	117.4 (5)
C8A—C7A—H7A	114.0 (5)	C7A—C6A—C5A	105.29 (13)
C6A—C7A—H7A	118.4 (5)	C7A—C6A—H6A	124.7 (6)
C4A—C5A—C6A	105.94 (13)	C5A—C6A—H6A	129.7 (6)
C4A—C5A—H5A	121.2 (7)	C7—C6—C5	105.86 (13)
C6A—C5A—H5A	132.4 (7)	C7—C6—H6	122.9 (7)
C4—C5—C6	105.63 (14)	C5—C6—H6	131.1 (6)
O3—C4—C9—O4	−69.7 (2)	C4—C5—C6—C7	0.3 (2)
O3—C4—C9—H9A	54 (1)	C4—C5—C6—H6	−175 (1)
O3—C4—C9—H9B	172.0 (5)	C4A—O3A—C7A—C8A	60.4 (2)
O3—C4—C3—C2	−78.5 (2)	C4A—O3A—C7A—C6A	−49.2 (3)
O3—C4—C3—C8	33.3 (3)	C4A—O3A—C7A—H7A	−177.9 (9)
O3—C4—C3—H3	158 (2)	C4A—C9A—O4A—H4A	80 (1)
O3—C4—C5—C6	−31.7 (4)	C4A—C3A—C8A—C1A	−112.1 (2)
O3—C4—C5—H5	159 (1)	C4A—C3A—C8A—C7A	1.9 (2)
O3—C7—C8—C1	73.8 (2)	C4A—C3A—C8A—H8A	127 (1)
O3—C7—C8—C3	−37.5 (3)	C4A—C5A—C6A—C7A	−0.6 (2)
O3—C7—C8—H8	−163 (1)	C4A—C5A—C6A—H6A	−175 (1)
O3—C7—C6—C5	31.3 (4)	C2—N1—C1—C8	2.1 (3)
O3—C7—C6—H6	−153 (2)	C2—C3—C4—C9	42.8 (3)
O2A—C2A—N1A—C1A	−178.87 (19)	C2—C3—C4—C5	176.5 (2)
O2A—C2A—N1A—H1A	7 (1)	C2—C3—C8—C1	4.2 (2)
O2A—C2A—C3A—C4A	−75.3 (2)	C2—C3—C8—C7	121.2 (3)
O2A—C2A—C3A—C8A	176.6 (2)	C2—C3—C8—H8	−116 (1)
O2A—C2A—C3A—H3A	50 (2)	C3—C2—N1—C1	0.7 (2)
O3A—C4A—C9A—O4A	172.34 (19)	C3—C4—O3—C7	−58.1 (2)
O3A—C4A—C9A—H9AB	51 (1)	C3—C4—C9—H9A	−62 (1)
O3A—C4A—C9A—H9AA	−64 (1)	C3—C4—C9—H9B	56.6 (10)
O3A—C4A—C3A—C2A	−76.6 (2)	C3—C4—C5—C6	72.5 (2)
O3A—C4A—C3A—C8A	34.1 (3)	C3—C4—C5—H5	−97 (1)
O3A—C4A—C3A—H3A	160 (2)	C3—C8—C7—C6	68.1 (3)
O3A—C4A—C5A—C6A	−30.8 (4)	C3—C8—C7—H7	−160 (1)
O3A—C4A—C5A—H5A	156 (1)	H3—C3—C4—C9	−81 (2)
O3A—C7A—C8A—C1A	72.6 (2)	H3—C3—C4—C5	53 (2)
O3A—C7A—C8A—C3A	−37.4 (3)	H3—C3—C8—C1	123 (1)
O3A—C7A—C8A—H8A	−165 (1)	H3—C3—C8—C7	−120 (1)
O3A—C7A—C6A—C5A	31.8 (4)	H3—C3—C8—H8	3 (2)
O3A—C7A—C6A—H6A	−154 (2)	C1A—N1A—C2A—C3A	1.3 (2)
O4A—C9A—C4A—C3A	56.8 (2)	C1A—C8A—C7A—C6A	178.8 (2)
O4A—C9A—C4A—C5A	−69.7 (2)	C1A—C8A—C7A—H7A	−49 (1)
O4—C9—C4—C3	174.89 (18)	C1A—C8A—C3A—H3A	127 (1)
O4—C9—C4—C5	47.5 (2)	C7A—O3A—C4A—C9A	175.9 (2)
H4—O4—C9—C4	76 (2)	C7A—O3A—C4A—C3A	−59.1 (2)
H4—O4—C9—H9A	−47 (2)	C7A—O3A—C4A—C5A	48.6 (3)
H4—O4—C9—H9B	−165 (3)	C7A—C8A—C3A—H3A	−119 (1)
O1—C1—N1—C2	−176.4 (2)	C7A—C6A—C5A—H5A	172 (2)
O1—C1—N1—H1	8 (1)	H7A—C7A—C8A—C3A	−159 (1)
O1—C1—C8—C7	65.0 (2)	H7A—C7A—C8A—H8A	74 (2)
O1—C1—C8—C3	174.5 (2)	H7A—C7A—C6A—C5A	157 (1)
O1—C1—C8—H8	−60 (1)	H7A—C7A—C6A—H6A	−29 (2)
O1A—C1A—N1A—C2A	−176.8 (2)	C5A—C4A—C9A—H9AB	169 (2)
O1A—C1A—N1A—H1A	−3 (1)	C5A—C4A—C9A—H9AA	54 (1)
O1A—C1A—C8A—C7A	66.4 (2)	C5A—C4A—C3A—C8A	−71.4 (2)
O1A—C1A—C8A—C3A	174.6 (2)	C5A—C4A—C3A—H3A	54 (2)
O1A—C1A—C8A—H8A	−59 (1)	C5A—C6A—C7A—C8A	−72.9 (3)
O2—C2—N1—C1	−179.2 (2)	H5A—C5A—C4A—C9A	33 (2)
O2—C2—N1—H1	−3 (1)	H5A—C5A—C4A—C3A	−99 (1)
O2—C2—C3—C4	−73.5 (2)	H5A—C5A—C6A—H6A	−2 (2)
O2—C2—C3—C8	176.8 (2)	C5—C4—O3—C7	49.4 (3)
O2—C2—C3—H3	53 (2)	C5—C4—C9—H9A	170.8 (7)
N1A—C2A—C3A—C4A	104.6 (2)	C5—C4—C9—H9B	−71 (1)
N1A—C2A—C3A—C8A	−3.6 (2)	C5—C4—C3—C8	−71.6 (2)
N1A—C2A—C3A—H3A	−131 (1)	C5—C6—C7—C8	−73.5 (3)
N1A—C1A—C8A—C7A	−112.0 (3)	C5—C6—C7—H7	155 (1)
N1A—C1A—C8A—C3A	−3.8 (2)	H5—C5—C4—C9	36 (2)
N1A—C1A—C8A—H8A	123 (1)	H5—C5—C6—C7	168 (2)
H1A—N1A—C2A—C3A	−173 (1)	H5—C5—C6—H6	−7 (2)
H1A—N1A—C1A—C8A	175.7 (8)	C8A—C7A—C6A—H6A	101 (2)
N1—C1—C8—C7	−113.4 (3)	C8A—C3A—C4A—C9A	155.7 (5)
N1—C1—C8—C3	−3.9 (2)	H8A—C8A—C7A—C6A	−59 (2)
N1—C1—C8—H8	122 (1)	H8A—C8A—C3A—H3A	5 (2)
N1—C2—C3—C4	106.5 (2)	C9—C4—O3—C7	176.4 (2)
N1—C2—C3—C8	−3.2 (2)	C9—C4—C3—C8	154.7 (5)
N1—C2—C3—H3	−127 (1)	C9—C4—C5—C6	−154.2 (6)
H1—N1—C1—C8	−174 (1)	C3A—C4A—C9A—H9AB	−64 (1)
H1—N1—C2—C3	176.7 (8)	C3A—C4A—C9A—H9AA	−179.9 (7)
C2A—N1A—C1A—C8A	1.7 (2)	C3A—C4A—C5A—C6A	73.8 (2)
C2A—C3A—C4A—C9A	45.0 (3)	C3A—C8A—C7A—C6A	68.9 (2)
C2A—C3A—C4A—C5A	177.9 (2)	H3A—C3A—C4A—C9A	−79 (2)
C2A—C3A—C8A—C1A	4.4 (2)	C1—C8—C7—C6	179.4 (2)
C2A—C3A—C8A—C7A	118.4 (3)	C1—C8—C7—H7	−48 (1)
C2A—C3A—C8A—H8A	−117 (1)	C9A—C4A—C5A—C6A	−154.0 (6)
C4—O3—C7—C8	60.1 (2)	H9AA—C9A—O4A—H4A	−42 (2)
C4—O3—C7—C6	−49.3 (3)	H9AB—C9A—O4A—H4A	−158 (2)
C4—O3—C7—H7	−176.1 (10)	C8—C7—C6—H6	102 (2)
C4—C3—C8—C1	−114.6 (2)	H8—C8—C7—C6	−58 (2)
C4—C3—C8—C7	2.4 (2)	H8—C8—C7—H7	75 (2)
C4—C3—C8—H8	125 (1)	H7—C7—C6—H6	−29 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O3A^i	1.10 (1)	2.62 (1)	3.2530 (16)	116 (1)
N1—H1···O1^ii	1.03 (1)	2.05 (1)	2.9307 (16)	142 (1)
O4—H4···O2A	0.97 (1)	1.81 (1)	2.7761 (14)	172 (1)
O4—H4···C2A	0.97 (1)	2.52 (1)	3.4059 (18)	151 (1)
C9A—H9AA···O2^iii	1.09 (1)	2.59 (1)	3.2779 (19)	120 (1)
C6A—H6A···O4A^iv	1.08 (1)	2.19 (1)	3.270 (2)	172 (1)
C6—H6···O2^iv	1.08 (1)	2.57 (1)	3.271 (2)	122 (1)
C5—H5···O2^v	1.08 (1)	2.45 (1)	3.4751 (19)	158 (1)
N1A—H1A···O3^vi	1.03 (1)	1.89 (1)	2.9019 (16)	165 (1)
N1—H1···O3A^vi	1.03 (1)	2.49 (1)	3.2773 (17)	132 (1)
C9—H9A···O1A^vi	1.09 (1)	2.49 (1)	3.5445 (19)	161 (1)
C9A—H9AB···O1^vi	1.09 (1)	2.55 (1)	3.5781 (19)	157 (1)
C8A—H8A···O1A^vii	1.10 (1)	2.37 (1)	3.2218 (17)	133 (1)
C7—H7···O1A^vii	1.10 (1)	2.22 (1)	3.169 (2)	143 (1)
C5A—H5A···O4^viii	1.08 (1)	2.40 (1)	3.2912 (18)	138 (1)
O4A—H4A···O4A^viii	0.97 (1)	2.52 (1)	2.882 (2)	102 (1)
O4A—H4A···O4^viii	0.97 (1)	1.86 (1)	2.8157 (14)	168 (1)

Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x+1/2, −y+1/2, z+1/2; (iv) x, y+1, z; (v) −x+3/2, y+1/2, −z+1/2; (vi) −x+1, −y+1, −z+1; (vii) −x+1, −y+2, −z+1; (viii) −x+2, −y+1, −z+1.