1-Methyl-3-(2-methyl-phen-yl)-3a-nitro-1,2,3,3a,4,9b-hexa-hydro-chromeno[4,3-b]pyrrole.

The asymmetric unit of the title compound, C(19)H(20)N(2)O(3), contains two independent mol-ecules in both of which the pyrrolidine ring adopts an envelope conformation, but with a C atom as the flap in one mol-ecule and the N atom in the other. The pyran ring adopts a half-chair conformation in both mol-ecules. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds and C-H⋯π inter-actions.

Related literature

For a related structure, see: Chitra Devi et al. (2011 ▶). For ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C19H20N2O3

M = 324.37

Monoclinic,

a = 17.8782 (13) Å

b = 8.0447 (6) Å

c = 23.4660 (17) Å

β = 97.605 (2)°

V = 3345.3 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.24 × 0.23 × 0.2 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.979, T max = 0.983

30608 measured reflections

8190 independent reflections

5303 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.149

S = 1.00

8190 reflections

437 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.24 e Å−3

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812020338/bt5906sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020338/bt5906Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812020338/bt5906Isup3.cml

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

C19H20N2O3	F(000) = 1376
Mr = 324.37	Dx = 1.288 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1223 reflections
a = 17.8782 (13) Å	θ = 1.4–28.4°
b = 8.0447 (6) Å	µ = 0.09 mm−1
c = 23.4660 (17) Å	T = 293 K
β = 97.605 (2)°	Block, colourless
V = 3345.3 (4) Å3	0.24 × 0.23 × 0.2 mm
Z = 8

Bruker SMART APEXII area-detector diffractometer	8190 independent reflections
Radiation source: fine-focus sealed tube	5303 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω and φ scans	θmax = 28.4°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −23→23
Tmin = 0.979, Tmax = 0.983	k = −10→10
30608 measured reflections	l = −31→31

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0745P)2 + 0.4617P] where P = (Fo2 + 2Fc2)/3
8190 reflections	(Δ/σ)max < 0.001
437 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.02218 (11)	0.2127 (2)	−0.20011 (6)	0.0595 (4)
C2	−0.04495 (16)	0.2582 (3)	−0.23344 (8)	0.0828 (7)
H2	−0.0427	0.3143	−0.2678	0.099*
C3	−0.11375 (15)	0.2233 (3)	−0.21748 (9)	0.0950 (8)
H3	−0.1575	0.2571	−0.2405	0.114*
C4	−0.11849 (11)	0.1391 (3)	−0.16774 (8)	0.0814 (6)
H4	−0.1653	0.1120	−0.1572	0.098*
C5	−0.05315 (9)	0.0942 (2)	−0.13315 (7)	0.0579 (4)
H5	−0.0566	0.0378	−0.0990	0.070*
C6	0.01721 (8)	0.13101 (18)	−0.14794 (6)	0.0453 (3)
C7	0.08806 (8)	0.08815 (19)	−0.10752 (6)	0.0451 (3)
H7	0.1301	0.0877	−0.1304	0.054*
C8	0.08968 (10)	−0.0800 (2)	−0.07584 (6)	0.0566 (4)
H8A	0.0398	−0.1295	−0.0804	0.068*
H8B	0.1241	−0.1562	−0.0911	0.068*
C9	0.15975 (7)	0.10856 (19)	−0.01373 (6)	0.0421 (3)
H9	0.2080	0.0871	−0.0279	0.051*
C10	0.10890 (8)	0.21210 (18)	−0.05732 (6)	0.0430 (3)
C11	0.04311 (8)	0.2785 (2)	−0.03001 (6)	0.0478 (4)
H11A	0.0113	0.3449	−0.0580	0.057*
H11B	0.0132	0.1859	−0.0192	0.057*
C12	0.12604 (8)	0.32064 (19)	0.05721 (6)	0.0456 (3)
C13	0.17300 (8)	0.19351 (19)	0.04372 (6)	0.0437 (3)
C14	0.23511 (9)	0.1557 (2)	0.08367 (7)	0.0633 (5)
H14	0.2687	0.0740	0.0751	0.076*
C15	0.24807 (12)	0.2370 (3)	0.13589 (8)	0.0778 (6)
H15	0.2894	0.2083	0.1624	0.093*
C16	0.19997 (11)	0.3598 (3)	0.14866 (7)	0.0712 (5)
H16	0.2085	0.4139	0.1839	0.085*
C17	0.13908 (10)	0.4035 (2)	0.10942 (7)	0.0586 (4)
H17	0.1068	0.4880	0.1178	0.070*
C18	0.15600 (10)	−0.1859 (2)	0.01335 (7)	0.0574 (4)
H18A	0.2014	−0.2047	−0.0035	0.086*
H18B	0.1248	−0.2834	0.0086	0.086*
H18C	0.1686	−0.1622	0.0536	0.086*
C19	0.09576 (14)	0.2474 (3)	−0.22223 (8)	0.0878 (7)
H19A	0.1217	0.1447	−0.2265	0.132*
H19B	0.1264	0.3176	−0.1955	0.132*
H19C	0.0862	0.3022	−0.2588	0.132*
N1	0.11522 (6)	−0.04540 (15)	−0.01501 (5)	0.0435 (3)
N2	0.15168 (10)	0.3563 (2)	−0.07917 (5)	0.0635 (4)
O1	0.11776 (11)	0.48303 (19)	−0.09268 (7)	0.1014 (5)
O2	0.21817 (9)	0.3339 (2)	−0.08460 (7)	0.0966 (5)
O3	0.06649 (6)	0.37738 (15)	0.01962 (4)	0.0589 (3)
C1'	0.55207 (10)	0.7413 (2)	0.25226 (7)	0.0575 (4)
C2'	0.62524 (12)	0.7853 (3)	0.27581 (8)	0.0763 (6)
H2'	0.6326	0.8360	0.3117	0.092*
C3'	0.68625 (12)	0.7563 (4)	0.24788 (10)	0.0930 (7)
H3'	0.7343	0.7873	0.2646	0.112*
C4'	0.67598 (11)	0.6809 (3)	0.19500 (9)	0.0865 (7)
H4'	0.7172	0.6615	0.1755	0.104*
C5'	0.60464 (10)	0.6338 (3)	0.17073 (7)	0.0665 (5)
H5'	0.5983	0.5821	0.1350	0.080*
C6'	0.54199 (9)	0.6622 (2)	0.19867 (6)	0.0516 (4)
C7'	0.46479 (9)	0.6026 (2)	0.17122 (7)	0.0526 (4)
H7'	0.4334	0.5847	0.2019	0.063*
C8'	0.46583 (10)	0.4408 (2)	0.13662 (7)	0.0598 (4)
H8'1	0.5135	0.3833	0.1461	0.072*
H8'2	0.4253	0.3675	0.1443	0.072*
C9'	0.39224 (8)	0.61203 (18)	0.07478 (6)	0.0468 (3)
H9'	0.3470	0.5529	0.0832	0.056*
C10'	0.42164 (8)	0.72296 (19)	0.12586 (7)	0.0503 (4)
C11'	0.47021 (10)	0.8579 (2)	0.10545 (8)	0.0618 (4)
H11C	0.4893	0.9281	0.1377	0.074*
H11D	0.5131	0.8076	0.0907	0.074*
C12'	0.39385 (9)	0.8719 (2)	0.01524 (7)	0.0526 (4)
C13'	0.37439 (8)	0.70552 (19)	0.01904 (7)	0.0478 (3)
C14'	0.33460 (9)	0.6325 (2)	−0.02933 (7)	0.0607 (4)
H14'	0.3195	0.5222	−0.0275	0.073*
C15'	0.31695 (11)	0.7189 (3)	−0.07995 (8)	0.0711 (5)
H15'	0.2916	0.6663	−0.1122	0.085*
C16'	0.33701 (11)	0.8836 (3)	−0.08254 (8)	0.0721 (5)
H16'	0.3250	0.9429	−0.1165	0.086*
C17'	0.37472 (10)	0.9603 (2)	−0.03502 (8)	0.0648 (5)
H17'	0.3874	1.0722	−0.0366	0.078*
C18'	0.44213 (11)	0.3545 (2)	0.03745 (8)	0.0638 (5)
H18D	0.4828	0.2763	0.0449	0.096*
H18E	0.4392	0.3937	−0.0014	0.096*
H18F	0.3955	0.3013	0.0429	0.096*
C19'	0.48834 (12)	0.7791 (3)	0.28559 (8)	0.0723 (5)
H19D	0.5081	0.8218	0.3227	0.108*
H19E	0.4603	0.6792	0.2901	0.108*
H19F	0.4557	0.8603	0.2653	0.108*
N1'	0.45555 (7)	0.49419 (15)	0.07680 (6)	0.0503 (3)
N2'	0.35723 (10)	0.8038 (2)	0.15211 (7)	0.0708 (4)
O1'	0.36829 (10)	0.9366 (2)	0.17476 (8)	0.1120 (6)
O2'	0.29936 (10)	0.7331 (3)	0.15009 (11)	0.1409 (9)
O3'	0.42965 (8)	0.95748 (14)	0.06165 (5)	0.0702 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0953 (12)	0.0420 (9)	0.0390 (7)	−0.0038 (9)	0.0005 (8)	−0.0055 (7)
C2	0.137 (2)	0.0639 (13)	0.0399 (8)	0.0232 (14)	−0.0154 (11)	−0.0052 (8)
C3	0.1028 (17)	0.112 (2)	0.0596 (12)	0.0460 (15)	−0.0303 (12)	−0.0294 (12)
C4	0.0604 (10)	0.1124 (18)	0.0670 (11)	0.0170 (11)	−0.0083 (9)	−0.0338 (12)
C5	0.0572 (9)	0.0653 (11)	0.0493 (8)	0.0002 (8)	−0.0003 (7)	−0.0102 (8)
C6	0.0576 (8)	0.0379 (8)	0.0386 (7)	−0.0013 (7)	−0.0003 (6)	−0.0057 (6)
C7	0.0500 (8)	0.0423 (8)	0.0422 (7)	−0.0030 (7)	0.0029 (6)	−0.0060 (6)
C8	0.0681 (10)	0.0417 (9)	0.0557 (9)	0.0025 (8)	−0.0074 (7)	−0.0034 (7)
C9	0.0373 (7)	0.0445 (8)	0.0444 (7)	0.0040 (6)	0.0046 (5)	−0.0028 (6)
C10	0.0505 (8)	0.0381 (8)	0.0396 (7)	−0.0048 (6)	0.0027 (6)	0.0006 (6)
C11	0.0508 (8)	0.0433 (8)	0.0463 (7)	0.0108 (7)	−0.0050 (6)	−0.0044 (6)
C12	0.0487 (8)	0.0437 (8)	0.0427 (7)	0.0020 (7)	0.0001 (6)	−0.0002 (6)
C13	0.0426 (7)	0.0434 (8)	0.0435 (7)	0.0007 (6)	0.0002 (6)	−0.0010 (6)
C14	0.0545 (9)	0.0682 (12)	0.0620 (9)	0.0129 (9)	−0.0115 (7)	−0.0090 (9)
C15	0.0794 (12)	0.0815 (14)	0.0628 (11)	0.0130 (11)	−0.0267 (9)	−0.0120 (10)
C16	0.0909 (13)	0.0687 (12)	0.0485 (9)	0.0011 (11)	−0.0121 (9)	−0.0154 (9)
C17	0.0725 (10)	0.0512 (10)	0.0505 (8)	0.0064 (8)	0.0025 (7)	−0.0093 (7)
C18	0.0648 (10)	0.0470 (9)	0.0595 (9)	0.0186 (8)	0.0050 (7)	0.0040 (8)
C19	0.1280 (18)	0.0886 (16)	0.0490 (9)	−0.0409 (14)	0.0193 (11)	0.0009 (10)
N1	0.0453 (6)	0.0355 (6)	0.0481 (6)	0.0064 (5)	0.0005 (5)	0.0005 (5)
N2	0.0918 (11)	0.0550 (10)	0.0434 (7)	−0.0256 (9)	0.0074 (7)	−0.0029 (7)
O1	0.1657 (16)	0.0489 (8)	0.0896 (10)	−0.0124 (10)	0.0174 (10)	0.0192 (8)
O2	0.0892 (10)	0.1105 (13)	0.0938 (10)	−0.0478 (10)	0.0260 (8)	0.0015 (9)
O3	0.0655 (7)	0.0546 (7)	0.0520 (6)	0.0232 (6)	−0.0089 (5)	−0.0131 (5)
C1'	0.0753 (11)	0.0482 (9)	0.0495 (8)	0.0097 (8)	0.0102 (8)	0.0058 (7)
C2'	0.0899 (14)	0.0777 (14)	0.0581 (10)	−0.0002 (11)	−0.0018 (9)	−0.0064 (10)
C3'	0.0700 (13)	0.122 (2)	0.0840 (14)	−0.0153 (13)	−0.0001 (11)	−0.0111 (14)
C4'	0.0569 (11)	0.121 (2)	0.0831 (13)	−0.0001 (12)	0.0162 (9)	−0.0044 (13)
C5'	0.0613 (10)	0.0808 (13)	0.0586 (9)	0.0073 (10)	0.0120 (8)	−0.0063 (9)
C6'	0.0564 (9)	0.0486 (9)	0.0504 (8)	0.0075 (7)	0.0094 (7)	0.0045 (7)
C7'	0.0547 (8)	0.0450 (9)	0.0597 (9)	0.0052 (7)	0.0134 (7)	0.0044 (7)
C8'	0.0667 (10)	0.0389 (8)	0.0731 (10)	0.0055 (8)	0.0069 (8)	0.0052 (8)
C9'	0.0464 (8)	0.0317 (7)	0.0635 (9)	−0.0029 (6)	0.0116 (6)	−0.0035 (7)
C10'	0.0513 (8)	0.0364 (8)	0.0631 (9)	0.0057 (7)	0.0079 (7)	−0.0049 (7)
C11'	0.0714 (10)	0.0366 (8)	0.0728 (10)	−0.0094 (8)	−0.0074 (8)	0.0014 (8)
C12'	0.0550 (9)	0.0368 (8)	0.0657 (9)	0.0025 (7)	0.0064 (7)	−0.0025 (7)
C13'	0.0453 (7)	0.0366 (8)	0.0621 (9)	0.0034 (6)	0.0089 (6)	−0.0047 (7)
C14'	0.0602 (10)	0.0477 (10)	0.0731 (11)	−0.0001 (8)	0.0045 (8)	−0.0128 (9)
C15'	0.0782 (12)	0.0709 (13)	0.0621 (10)	0.0071 (10)	0.0010 (9)	−0.0137 (10)
C16'	0.0832 (13)	0.0721 (13)	0.0612 (10)	0.0139 (11)	0.0107 (9)	0.0044 (10)
C17'	0.0777 (11)	0.0460 (9)	0.0713 (11)	0.0043 (9)	0.0119 (9)	0.0064 (9)
C18'	0.0774 (11)	0.0334 (8)	0.0827 (12)	0.0009 (8)	0.0189 (9)	−0.0100 (8)
C19'	0.0963 (14)	0.0680 (12)	0.0558 (9)	0.0215 (11)	0.0220 (9)	0.0034 (9)
N1'	0.0574 (7)	0.0292 (6)	0.0654 (8)	0.0036 (6)	0.0122 (6)	−0.0013 (6)
N2'	0.0712 (10)	0.0674 (11)	0.0719 (9)	0.0242 (9)	0.0024 (8)	−0.0161 (8)
O1'	0.1246 (13)	0.0847 (11)	0.1221 (13)	0.0457 (10)	−0.0010 (10)	−0.0476 (11)
O2'	0.0779 (11)	0.1486 (18)	0.208 (2)	−0.0084 (12)	0.0644 (13)	−0.0781 (17)
O3'	0.0954 (9)	0.0313 (6)	0.0773 (8)	−0.0069 (6)	−0.0131 (7)	0.0029 (6)

C1—C2	1.392 (3)	C1'—C2'	1.396 (3)
C1—C6	1.402 (2)	C1'—C6'	1.399 (2)
C1—C19	1.503 (3)	C1'—C19'	1.496 (2)
C2—C3	1.361 (3)	C2'—C3'	1.365 (3)
C2—H2	0.9300	C2'—H2'	0.9300
C3—C4	1.362 (3)	C3'—C4'	1.372 (3)
C3—H3	0.9300	C3'—H3'	0.9300
C4—C5	1.379 (2)	C4'—C5'	1.379 (3)
C4—H4	0.9300	C4'—H4'	0.9300
C5—C6	1.381 (2)	C5'—C6'	1.390 (2)
C5—H5	0.9300	C5'—H5'	0.9300
C6—C7	1.5183 (19)	C6'—C7'	1.521 (2)
C7—C8	1.542 (2)	C7'—C8'	1.535 (2)
C7—C10	1.5507 (19)	C7'—C10'	1.565 (2)
C7—H7	0.9800	C7'—H7'	0.9800
C8—N1	1.4666 (18)	C8'—N1'	1.456 (2)
C8—H8A	0.9700	C8'—H8'1	0.9700
C8—H8B	0.9700	C8'—H8'2	0.9700
C9—N1	1.4705 (19)	C9'—N1'	1.4724 (19)
C9—C13	1.5020 (19)	C9'—C13'	1.506 (2)
C9—C10	1.5234 (19)	C9'—C10'	1.531 (2)
C9—H9	0.9800	C9'—H9'	0.9800
C10—C11	1.510 (2)	C10'—C11'	1.507 (2)
C10—N2	1.516 (2)	C10'—N2'	1.522 (2)
C11—O3	1.4266 (17)	C11'—O3'	1.424 (2)
C11—H11A	0.9700	C11'—H11C	0.9700
C11—H11B	0.9700	C11'—H11D	0.9700
C12—O3	1.3679 (16)	C12'—O3'	1.3730 (19)
C12—C13	1.386 (2)	C12'—C17'	1.381 (2)
C12—C17	1.387 (2)	C12'—C13'	1.389 (2)
C13—C14	1.389 (2)	C13'—C14'	1.388 (2)
C14—C15	1.381 (2)	C14'—C15'	1.376 (3)
C14—H14	0.9300	C14'—H14'	0.9300
C15—C16	1.369 (3)	C15'—C16'	1.376 (3)
C15—H15	0.9300	C15'—H15'	0.9300
C16—C17	1.375 (2)	C16'—C17'	1.371 (3)
C16—H16	0.9300	C16'—H16'	0.9300
C17—H17	0.9300	C17'—H17'	0.9300
C18—N1	1.4576 (19)	C18'—N1'	1.454 (2)
C18—H18A	0.9600	C18'—H18D	0.9600
C18—H18B	0.9600	C18'—H18E	0.9600
C18—H18C	0.9600	C18'—H18F	0.9600
C19—H19A	0.9600	C19'—H19D	0.9600
C19—H19B	0.9600	C19'—H19E	0.9600
C19—H19C	0.9600	C19'—H19F	0.9600
N2—O1	1.207 (2)	N2'—O2'	1.176 (2)
N2—O2	1.226 (2)	N2'—O1'	1.198 (2)
C2—C1—C6	117.65 (19)	C2'—C1'—C6'	118.24 (16)
C2—C1—C19	119.08 (18)	C2'—C1'—C19'	118.69 (17)
C6—C1—C19	123.24 (16)	C6'—C1'—C19'	123.06 (17)
C3—C2—C1	122.31 (19)	C3'—C2'—C1'	122.21 (18)
C3—C2—H2	118.8	C3'—C2'—H2'	118.9
C1—C2—H2	118.8	C1'—C2'—H2'	118.9
C2—C3—C4	119.94 (18)	C2'—C3'—C4'	119.36 (19)
C2—C3—H3	120.0	C2'—C3'—H3'	120.3
C4—C3—H3	120.0	C4'—C3'—H3'	120.3
C3—C4—C5	119.4 (2)	C3'—C4'—C5'	120.05 (19)
C3—C4—H4	120.3	C3'—C4'—H4'	120.0
C5—C4—H4	120.3	C5'—C4'—H4'	120.0
C4—C5—C6	121.66 (18)	C4'—C5'—C6'	121.26 (17)
C4—C5—H5	119.2	C4'—C5'—H5'	119.4
C6—C5—H5	119.2	C6'—C5'—H5'	119.4
C5—C6—C1	119.01 (15)	C5'—C6'—C1'	118.87 (15)
C5—C6—C7	120.46 (13)	C5'—C6'—C7'	119.41 (14)
C1—C6—C7	120.51 (14)	C1'—C6'—C7'	121.70 (14)
C6—C7—C8	117.47 (13)	C6'—C7'—C8'	114.66 (13)
C6—C7—C10	115.17 (12)	C6'—C7'—C10'	115.53 (13)
C8—C7—C10	102.16 (11)	C8'—C7'—C10'	101.78 (12)
C6—C7—H7	107.1	C6'—C7'—H7'	108.2
C8—C7—H7	107.1	C8'—C7'—H7'	108.2
C10—C7—H7	107.1	C10'—C7'—H7'	108.2
N1—C8—C7	106.62 (12)	N1'—C8'—C7'	104.55 (13)
N1—C8—H8A	110.4	N1'—C8'—H8'1	110.8
C7—C8—H8A	110.4	C7'—C8'—H8'1	110.8
N1—C8—H8B	110.4	N1'—C8'—H8'2	110.8
C7—C8—H8B	110.4	C7'—C8'—H8'2	110.8
H8A—C8—H8B	108.6	H8'1—C8'—H8'2	108.9
N1—C9—C13	114.98 (11)	N1'—C9'—C13'	115.03 (12)
N1—C9—C10	99.98 (10)	N1'—C9'—C10'	99.63 (11)
C13—C9—C10	111.29 (12)	C13'—C9'—C10'	113.60 (12)
N1—C9—H9	110.1	N1'—C9'—H9'	109.4
C13—C9—H9	110.1	C13'—C9'—H9'	109.4
C10—C9—H9	110.1	C10'—C9'—H9'	109.4
C11—C10—N2	109.22 (13)	C11'—C10'—N2'	108.64 (14)
C11—C10—C9	109.73 (11)	C11'—C10'—C9'	108.88 (13)
N2—C10—C9	111.27 (12)	N2'—C10'—C9'	111.49 (12)
C11—C10—C7	115.32 (11)	C11'—C10'—C7'	114.13 (13)
N2—C10—C7	108.45 (11)	N2'—C10'—C7'	108.68 (13)
C9—C10—C7	102.74 (11)	C9'—C10'—C7'	105.03 (12)
O3—C11—C10	112.54 (11)	O3'—C11'—C10'	112.02 (13)
O3—C11—H11A	109.1	O3'—C11'—H11C	109.2
C10—C11—H11A	109.1	C10'—C11'—H11C	109.2
O3—C11—H11B	109.1	O3'—C11'—H11D	109.2
C10—C11—H11B	109.1	C10'—C11'—H11D	109.2
H11A—C11—H11B	107.8	H11C—C11'—H11D	107.9
O3—C12—C13	122.84 (12)	O3'—C12'—C17'	117.13 (14)
O3—C12—C17	115.78 (13)	O3'—C12'—C13'	121.77 (14)
C13—C12—C17	121.33 (13)	C17'—C12'—C13'	121.03 (15)
C12—C13—C14	117.51 (14)	C14'—C13'—C12'	117.46 (15)
C12—C13—C9	120.82 (12)	C14'—C13'—C9'	121.72 (14)
C14—C13—C9	121.55 (14)	C12'—C13'—C9'	120.74 (14)
C15—C14—C13	121.36 (17)	C15'—C14'—C13'	121.74 (17)
C15—C14—H14	119.3	C15'—C14'—H14'	119.1
C13—C14—H14	119.3	C13'—C14'—H14'	119.1
C16—C15—C14	119.96 (16)	C16'—C15'—C14'	119.55 (17)
C16—C15—H15	120.0	C16'—C15'—H15'	120.2
C14—C15—H15	120.0	C14'—C15'—H15'	120.2
C15—C16—C17	120.16 (16)	C17'—C16'—C15'	120.04 (18)
C15—C16—H16	119.9	C17'—C16'—H16'	120.0
C17—C16—H16	119.9	C15'—C16'—H16'	120.0
C16—C17—C12	119.64 (16)	C16'—C17'—C12'	120.13 (17)
C16—C17—H17	120.2	C16'—C17'—H17'	119.9
C12—C17—H17	120.2	C12'—C17'—H17'	119.9
N1—C18—H18A	109.5	N1'—C18'—H18D	109.5
N1—C18—H18B	109.5	N1'—C18'—H18E	109.5
H18A—C18—H18B	109.5	H18D—C18'—H18E	109.5
N1—C18—H18C	109.5	N1'—C18'—H18F	109.5
H18A—C18—H18C	109.5	H18D—C18'—H18F	109.5
H18B—C18—H18C	109.5	H18E—C18'—H18F	109.5
C1—C19—H19A	109.5	C1'—C19'—H19D	109.5
C1—C19—H19B	109.5	C1'—C19'—H19E	109.5
H19A—C19—H19B	109.5	H19D—C19'—H19E	109.5
C1—C19—H19C	109.5	C1'—C19'—H19F	109.5
H19A—C19—H19C	109.5	H19D—C19'—H19F	109.5
H19B—C19—H19C	109.5	H19E—C19'—H19F	109.5
C18—N1—C8	111.69 (12)	C18'—N1'—C8'	111.94 (13)
C18—N1—C9	114.03 (11)	C18'—N1'—C9'	114.55 (12)
C8—N1—C9	106.14 (11)	C8'—N1'—C9'	102.66 (12)
O1—N2—O2	123.89 (18)	O2'—N2'—O1'	122.81 (19)
O1—N2—C10	118.48 (17)	O2'—N2'—C10'	119.06 (17)
O2—N2—C10	117.53 (17)	O1'—N2'—C10'	118.12 (18)
C12—O3—C11	117.34 (11)	C12'—O3'—C11'	115.47 (12)
C6—C1—C2—C3	−1.2 (3)	C6'—C1'—C2'—C3'	1.2 (3)
C19—C1—C2—C3	176.7 (2)	C19'—C1'—C2'—C3'	−179.5 (2)
C1—C2—C3—C4	−1.0 (3)	C1'—C2'—C3'—C4'	−0.3 (4)
C2—C3—C4—C5	1.9 (3)	C2'—C3'—C4'—C5'	−0.6 (4)
C3—C4—C5—C6	−0.7 (3)	C3'—C4'—C5'—C6'	0.5 (4)
C4—C5—C6—C1	−1.5 (3)	C4'—C5'—C6'—C1'	0.5 (3)
C4—C5—C6—C7	176.76 (16)	C4'—C5'—C6'—C7'	−177.83 (19)
C2—C1—C6—C5	2.4 (2)	C2'—C1'—C6'—C5'	−1.3 (3)
C19—C1—C6—C5	−175.46 (17)	C19'—C1'—C6'—C5'	179.42 (17)
C2—C1—C6—C7	−175.85 (15)	C2'—C1'—C6'—C7'	177.01 (16)
C19—C1—C6—C7	6.3 (2)	C19'—C1'—C6'—C7'	−2.3 (2)
C5—C6—C7—C8	40.3 (2)	C5'—C6'—C7'—C8'	33.4 (2)
C1—C6—C7—C8	−141.51 (15)	C1'—C6'—C7'—C8'	−144.85 (15)
C5—C6—C7—C10	−80.15 (18)	C5'—C6'—C7'—C10'	−84.50 (19)
C1—C6—C7—C10	98.06 (16)	C1'—C6'—C7'—C10'	97.23 (18)
C6—C7—C8—N1	−131.16 (13)	C6'—C7'—C8'—N1'	−103.29 (15)
C10—C7—C8—N1	−4.12 (16)	C10'—C7'—C8'—N1'	22.18 (15)
N1—C9—C10—C11	77.41 (13)	N1'—C9'—C10'—C11'	86.74 (14)
C13—C9—C10—C11	−44.51 (16)	C13'—C9'—C10'—C11'	−36.11 (17)
N1—C9—C10—N2	−161.60 (11)	N1'—C9'—C10'—N2'	−153.42 (13)
C13—C9—C10—N2	76.48 (15)	C13'—C9'—C10'—N2'	83.73 (16)
N1—C9—C10—C7	−45.74 (13)	N1'—C9'—C10'—C7'	−35.89 (14)
C13—C9—C10—C7	−167.66 (11)	C13'—C9'—C10'—C7'	−158.74 (12)
C6—C7—C10—C11	39.70 (18)	C6'—C7'—C10'—C11'	14.51 (19)
C8—C7—C10—C11	−88.80 (15)	C8'—C7'—C10'—C11'	−110.37 (15)
C6—C7—C10—N2	−83.10 (16)	C6'—C7'—C10'—N2'	−106.91 (15)
C8—C7—C10—N2	148.40 (14)	C8'—C7'—C10'—N2'	128.21 (14)
C6—C7—C10—C9	159.04 (12)	C6'—C7'—C10'—C9'	133.68 (13)
C8—C7—C10—C9	30.53 (14)	C8'—C7'—C10'—C9'	8.79 (15)
N2—C10—C11—O3	−63.92 (15)	N2'—C10'—C11'—O3'	−62.29 (18)
C9—C10—C11—O3	58.29 (16)	C9'—C10'—C11'—O3'	59.30 (18)
C7—C10—C11—O3	173.69 (12)	C7'—C10'—C11'—O3'	176.27 (13)
O3—C12—C13—C14	174.98 (15)	O3'—C12'—C13'—C14'	176.47 (15)
C17—C12—C13—C14	−2.1 (2)	C17'—C12'—C13'—C14'	−0.5 (2)
O3—C12—C13—C9	−0.9 (2)	O3'—C12'—C13'—C9'	−0.1 (2)
C17—C12—C13—C9	−177.98 (14)	C17'—C12'—C13'—C9'	−177.13 (15)
N1—C9—C13—C12	−94.95 (16)	N1'—C9'—C13'—C14'	78.02 (18)
C10—C9—C13—C12	17.80 (19)	C10'—C9'—C13'—C14'	−168.05 (14)
N1—C9—C13—C14	89.33 (18)	N1'—C9'—C13'—C12'	−105.52 (16)
C10—C9—C13—C14	−157.91 (15)	C10'—C9'—C13'—C12'	8.41 (19)
C12—C13—C14—C15	2.6 (3)	C12'—C13'—C14'—C15'	2.1 (2)
C9—C13—C14—C15	178.41 (17)	C9'—C13'—C14'—C15'	178.67 (15)
C13—C14—C15—C16	−1.3 (3)	C13'—C14'—C15'—C16'	−2.1 (3)
C14—C15—C16—C17	−0.5 (3)	C14'—C15'—C16'—C17'	0.4 (3)
C15—C16—C17—C12	1.0 (3)	C15'—C16'—C17'—C12'	1.1 (3)
O3—C12—C17—C16	−176.89 (16)	O3'—C12'—C17'—C16'	−178.20 (16)
C13—C12—C17—C16	0.4 (3)	C13'—C12'—C17'—C16'	−1.1 (3)
C7—C8—N1—C18	−150.02 (13)	C7'—C8'—N1'—C18'	−170.11 (13)
C7—C8—N1—C9	−25.18 (15)	C7'—C8'—N1'—C9'	−46.77 (15)
C13—C9—N1—C18	−73.23 (15)	C13'—C9'—N1'—C18'	−65.66 (17)
C10—C9—N1—C18	167.51 (12)	C10'—C9'—N1'—C18'	172.51 (13)
C13—C9—N1—C8	163.38 (12)	C13'—C9'—N1'—C8'	172.76 (12)
C10—C9—N1—C8	44.12 (13)	C10'—C9'—N1'—C8'	50.93 (14)
C11—C10—N2—O1	−27.39 (18)	C11'—C10'—N2'—O2'	150.5 (2)
C9—C10—N2—O1	−148.68 (15)	C9'—C10'—N2'—O2'	30.5 (3)
C7—C10—N2—O1	99.03 (17)	C7'—C10'—N2'—O2'	−84.8 (2)
C11—C10—N2—O2	156.01 (14)	C11'—C10'—N2'—O1'	−30.5 (2)
C9—C10—N2—O2	34.72 (18)	C9'—C10'—N2'—O1'	−150.48 (17)
C7—C10—N2—O2	−77.57 (16)	C7'—C10'—N2'—O1'	94.22 (19)
C13—C12—O3—C11	13.4 (2)	C17'—C12'—O3'—C11'	−160.04 (15)
C17—C12—O3—C11	−169.35 (14)	C13'—C12'—O3'—C11'	22.9 (2)
C10—C11—O3—C12	−42.60 (18)	C10'—C11'—O3'—C12'	−53.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1′i	0.93	2.60	3.282 (3)	131
C4′—H4′···O2ii	0.93	2.56	3.407 (3)	152
C14′—H14′···O2	0.93	2.59	3.327 (2)	136
C19′—H19F···O1′	0.96	2.54	3.391 (3)	148
C18—H18A···Cg11i	0.96	2.92	3.854 (2)	166
C19′—H19E···Cg3iii	0.96	2.94	3.811 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

Cg11 and Cg3 are the centroids of the C12′–C17′ and C1–C6 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O1′i	0.93	2.60	3.282 (3)	131
C4′—H4′⋯O2ii	0.93	2.56	3.407 (3)	152
C14′—H14′⋯O2	0.93	2.59	3.327 (2)	136
C19′—H19F⋯O1′	0.96	2.54	3.391 (3)	148
C18—H18A⋯Cg11i	0.96	2.92	3.854 (2)	166
C19′—H19E⋯Cg3iii	0.96	2.94	3.811 (3)	152

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