Tetra­methyl-1-(4-chloro­benz­yl)-3a,7a-dihydro-1H-indole-2,3,3a,4-tetra­carboxyl­ate

In the title compound, C₂₃H₂₂ClNO₈, the core structure, which consists of fused cyclo­hexa­diene and pyrrole rings, is bent with a dihedral angle of 64.11 (5)° between the ring planes owing to a lack of π conjugation within the heterobicycle. Mol­ecules are linked by an extensive network of inter­molecular C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 446 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.036
• wR factor = 0.102
• Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........      \PC20

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C7     = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C8     = ...          R

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

   3 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

The reaction of N-(4-chlorobenzyl)-1H-pyrrole with dimethyl acetylenedicarboxylate (DMAD) leads to the formation of the title compound, (I), (Fig. 1), via initial Diels-Alder addition to form a 7-azanorbornadiene intermediate and subsequent Michael-type addition of the second molecule of DMAD (Acheson & Vernon, 1962; Jones & Bean, 1977; Lee et al., 1978).

The title compound, (I), crystallizes as a racemic mixture in the centrosymmetric space group P2₁/c and the C7-S and C8-R isomer is shown in Fig. 1. Owing to a lack of π-conjugation within the hetero-bicycle of (I), the core structure is bent. The dihedral angle between the cyclohexadiene and pyrrole rings is 64.11 (5)° compared to the indole compound which was planar (Roychowdhury & Basak, 1975). The torsion angles C4–C7–C8–C1 and C5–C7–C8–N1 are 31.1 (2) Å and 26.2 (1) Å, respectively, indicating a syn-configuration at chiral centers of the moiety hetero-bicycle, similar to that of the related compound reported by Preut et al. (1991). In pyrrole unit, the N1–C6 distance (1.351 (2) Å) is similar with that of C6–C5 (1.356 (2) Å) and the sum of the bond angle around N1 is 359.4°. These facts indicate that a lone pair of nitrogen atom (N1) is delocalized. The dihedral angle between the plane of the benzene ring and the plane of the ester group attached on C7 is 7.37 (9)°, indicating an almost face-to-face orientation.

The crystal packing of (I) is stabilized by weak intermolecular C–H···O hydrogen bonds, Table 1. The dihedral angle between the pyrrole and benzene rings is 81.19 (6)° and there is no evidence of π–π intermolecular interactions between benzene rings in the crystal packing.

Related literature

For details of the preparations of (I) and related compounds, see: Acheson & Vernon (1962); Jones & Bean (1977); Lee et al. (1978). For related structures, see: Roychowdhury & Basak (1975); Preut et al. (1991).

S2. Experimental

Compound (I) was prepared by literature methods (Lee et al., 1978). Crystals of (I) were obtained by slow evaporation of a methanol solution in a refrigerator.

S3. Refinement

All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.93 Å, U_iso=1.2U_eq (C) for aromatic 0.98 Å, U_iso = 1.2U_eq (C) for CH, 0.97 Å, U_iso = 1.2U_eq (C) for CH₂ and 0.96 Å, U_iso = 1.5U_eq (C) for CH₃ atoms.

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Bruker, 2000); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures

	Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level for non-H atoms. All H atoms except hydrogen atom at the chiral center are omitted for clarity.
	Fig. 2. The crystal packing in the title compound, viewed down the a axis. Dashed lines indicate C–H···O hydrogen bonds.

Tetramethyl-1-(4-chlorobenzyl)-3a,7a-dihydro-1H-indole-2,3,3a,4- tetracarboxylate

Crystal data

C23H22ClNO8	F(000) = 992
Mr = 475.87	Dx = 1.402 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6747 reflections
a = 12.8844 (8) Å	θ = 2.4–28.2°
b = 12.3350 (7) Å	µ = 0.22 mm^−1
c = 15.3485 (9) Å	T = 446 K
β = 112.471 (1)°	Block, yellow
V = 2254.1 (2) Å^3	0.50 × 0.35 × 0.35 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	3989 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 27.5°, θmin = 1.8°
φ and ω scans	h = −16→16
13936 measured reflections	k = −15→14
5132 independent reflections	l = −19→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.102	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0471P)^2 + 0.7066P] where P = (Fo^2 + 2Fc^2)/3
5132 reflections	(Δ/σ)max < 0.001
298 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.34 e Å^−3

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
Cl1	0.81143 (4)	0.32249 (4)	0.20324 (3)	0.04669 (13)
O1	0.45128 (10)	0.85362 (10)	−0.04992 (8)	0.0398 (3)
O2	0.33449 (9)	0.91151 (9)	−0.19189 (8)	0.0325 (3)
O3	0.69018 (9)	0.76987 (9)	0.03583 (7)	0.0326 (3)
O4	0.55635 (9)	0.64221 (9)	−0.01694 (7)	0.0311 (2)
O5	0.77351 (9)	0.98920 (9)	−0.13061 (8)	0.0353 (3)
O6	0.59618 (9)	0.98517 (8)	−0.13705 (8)	0.0305 (2)
O7	0.89923 (10)	0.81442 (11)	−0.20986 (8)	0.0422 (3)
O8	0.95022 (9)	0.81130 (10)	−0.05262 (8)	0.0352 (3)
N1	0.74121 (10)	0.65145 (10)	−0.15598 (9)	0.0271 (3)
C1	0.55594 (13)	0.62580 (13)	−0.28022 (11)	0.0290 (3)
H1	0.5841	0.5799	−0.3140	0.035*
C2	0.46045 (13)	0.67819 (13)	−0.32558 (10)	0.0297 (3)
H2	0.4229	0.6680	−0.3901	0.036*
C3	0.41351 (12)	0.75158 (12)	−0.27551 (10)	0.0252 (3)
H3	0.3411	0.7780	−0.3066	0.030*
C4	0.47138 (11)	0.78200 (11)	−0.18640 (10)	0.0216 (3)
C5	0.68261 (11)	0.82092 (12)	−0.14121 (10)	0.0235 (3)
C6	0.76738 (12)	0.75793 (12)	−0.14440 (9)	0.0247 (3)
C7	0.59195 (11)	0.74492 (11)	−0.13385 (9)	0.0209 (3)
C8	0.61985 (11)	0.63855 (12)	−0.17588 (10)	0.0242 (3)
H8	0.6078	0.5753	−0.1423	0.029*
C9	0.42044 (12)	0.85190 (12)	−0.13475 (10)	0.0253 (3)
C10	0.27820 (17)	0.97607 (16)	−0.14419 (15)	0.0472 (5)
H10A	0.2180	1.0161	−0.1899	0.071*
H10B	0.3308	1.0256	−0.1017	0.071*
H10C	0.2485	0.9293	−0.1094	0.071*
C11	0.61854 (12)	0.72414 (12)	−0.02791 (10)	0.0239 (3)
C12	0.57395 (16)	0.61703 (15)	0.07972 (11)	0.0397 (4)
H12A	0.5260	0.5580	0.0810	0.060*
H12B	0.5565	0.6795	0.1089	0.060*
H12C	0.6510	0.5969	0.1135	0.060*
C13	0.69099 (12)	0.93752 (12)	−0.13481 (10)	0.0243 (3)
C14	0.59806 (16)	1.10186 (13)	−0.13296 (13)	0.0374 (4)
H14A	0.5269	1.1279	−0.1352	0.056*
H14B	0.6122	1.1303	−0.1856	0.056*
H14C	0.6564	1.1251	−0.0753	0.056*
C15	0.87881 (12)	0.79818 (13)	−0.14117 (10)	0.0275 (3)
C16	1.05624 (14)	0.86206 (17)	−0.04081 (14)	0.0451 (4)
H16A	1.1019	0.8681	0.0252	0.068*
H16B	1.0425	0.9330	−0.0687	0.068*
H16C	1.0946	0.8187	−0.0711	0.068*
C17	0.81662 (13)	0.55840 (13)	−0.13847 (11)	0.0309 (3)
H17A	0.8915	0.5832	−0.1293	0.037*
H17B	0.7909	0.5106	−0.1928	0.037*
C18	0.82047 (12)	0.49683 (12)	−0.05216 (10)	0.0273 (3)
C19	0.75483 (14)	0.40459 (13)	−0.06175 (12)	0.0367 (4)
H19	0.7134	0.3777	−0.1217	0.044*
C20	0.75027 (15)	0.35201 (14)	0.01665 (12)	0.0385 (4)
H20	0.7047	0.2915	0.0097	0.046*
C21	0.81471 (13)	0.39120 (13)	0.10511 (11)	0.0307 (3)
C22	0.88103 (13)	0.48238 (13)	0.11721 (11)	0.0298 (3)
H22	0.9239	0.5076	0.1774	0.036*
C23	0.88276 (12)	0.53567 (13)	0.03828 (11)	0.0286 (3)
H23	0.9259	0.5980	0.0457	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0551 (3)	0.0451 (3)	0.0408 (2)	−0.0104 (2)	0.0193 (2)	0.00712 (19)
O1	0.0433 (7)	0.0506 (7)	0.0282 (6)	0.0109 (6)	0.0167 (5)	−0.0020 (5)
O2	0.0314 (6)	0.0317 (6)	0.0380 (6)	0.0096 (5)	0.0173 (5)	0.0041 (5)
O3	0.0308 (6)	0.0401 (6)	0.0207 (5)	−0.0090 (5)	0.0029 (4)	−0.0025 (4)
O4	0.0368 (6)	0.0330 (6)	0.0227 (5)	−0.0092 (5)	0.0105 (5)	0.0017 (4)
O5	0.0313 (6)	0.0327 (6)	0.0439 (7)	−0.0088 (5)	0.0166 (5)	−0.0001 (5)
O6	0.0300 (5)	0.0242 (5)	0.0386 (6)	−0.0011 (4)	0.0147 (5)	−0.0027 (4)
O7	0.0346 (6)	0.0659 (9)	0.0307 (6)	−0.0049 (6)	0.0176 (5)	0.0026 (6)
O8	0.0209 (5)	0.0550 (7)	0.0267 (6)	−0.0030 (5)	0.0059 (4)	−0.0013 (5)
N1	0.0206 (6)	0.0286 (7)	0.0306 (7)	0.0043 (5)	0.0079 (5)	0.0017 (5)
C1	0.0287 (8)	0.0320 (8)	0.0265 (8)	−0.0002 (6)	0.0107 (6)	−0.0079 (6)
C2	0.0291 (8)	0.0369 (8)	0.0195 (7)	−0.0016 (6)	0.0053 (6)	−0.0054 (6)
C3	0.0199 (6)	0.0299 (8)	0.0233 (7)	0.0017 (6)	0.0052 (5)	0.0020 (6)
C4	0.0194 (6)	0.0227 (7)	0.0221 (7)	−0.0011 (5)	0.0072 (5)	0.0020 (5)
C5	0.0202 (7)	0.0286 (7)	0.0204 (7)	−0.0015 (6)	0.0065 (5)	0.0021 (5)
C6	0.0217 (7)	0.0332 (8)	0.0175 (6)	0.0002 (6)	0.0056 (5)	0.0030 (6)
C7	0.0191 (6)	0.0228 (7)	0.0195 (6)	−0.0010 (5)	0.0058 (5)	−0.0003 (5)
C8	0.0213 (7)	0.0253 (7)	0.0245 (7)	0.0008 (5)	0.0071 (6)	0.0000 (6)
C9	0.0230 (7)	0.0260 (7)	0.0285 (8)	−0.0021 (6)	0.0117 (6)	0.0003 (6)
C10	0.0501 (11)	0.0436 (10)	0.0625 (12)	0.0198 (9)	0.0379 (10)	0.0090 (9)
C11	0.0216 (7)	0.0255 (7)	0.0232 (7)	0.0013 (6)	0.0070 (6)	0.0011 (5)
C12	0.0509 (10)	0.0430 (10)	0.0263 (8)	−0.0086 (8)	0.0159 (8)	0.0056 (7)
C13	0.0258 (7)	0.0288 (7)	0.0180 (6)	−0.0035 (6)	0.0080 (5)	0.0002 (5)
C14	0.0479 (10)	0.0251 (8)	0.0403 (9)	0.0016 (7)	0.0180 (8)	−0.0034 (7)
C15	0.0219 (7)	0.0350 (8)	0.0256 (7)	0.0023 (6)	0.0089 (6)	0.0020 (6)
C16	0.0218 (8)	0.0564 (12)	0.0529 (11)	−0.0061 (8)	0.0095 (8)	−0.0097 (9)
C17	0.0293 (8)	0.0363 (8)	0.0270 (8)	0.0114 (7)	0.0107 (6)	0.0015 (6)
C18	0.0256 (7)	0.0278 (8)	0.0265 (7)	0.0097 (6)	0.0078 (6)	−0.0001 (6)
C19	0.0400 (9)	0.0294 (8)	0.0291 (8)	0.0020 (7)	0.0002 (7)	−0.0047 (7)
C20	0.0395 (9)	0.0263 (8)	0.0392 (9)	−0.0054 (7)	0.0031 (7)	−0.0002 (7)
C21	0.0319 (8)	0.0282 (8)	0.0313 (8)	0.0028 (6)	0.0113 (7)	0.0026 (6)
C22	0.0300 (8)	0.0307 (8)	0.0257 (8)	−0.0011 (6)	0.0074 (6)	−0.0043 (6)
C23	0.0256 (7)	0.0279 (8)	0.0302 (8)	−0.0005 (6)	0.0085 (6)	−0.0017 (6)

Geometric parameters (Å, º)

Cl1—C21	1.7428 (16)	C7—C11	1.5495 (19)
O1—C9	1.2074 (18)	C7—C8	1.5634 (19)
O2—C9	1.3393 (18)	C8—H8	0.9800
O2—C10	1.4499 (19)	C10—H10A	0.9600
O3—C11	1.1988 (17)	C10—H10B	0.9600
O4—C11	1.3397 (18)	C10—H10C	0.9600
O4—C12	1.4464 (18)	C12—H12A	0.9600
O5—C13	1.2201 (17)	C12—H12B	0.9600
O6—C13	1.3441 (18)	C12—H12C	0.9600
O6—C14	1.4405 (19)	C14—H14A	0.9600
O7—C15	1.1971 (18)	C14—H14B	0.9600
O8—C15	1.3281 (18)	C14—H14C	0.9600
O8—C16	1.450 (2)	C16—H16A	0.9600
N1—C6	1.351 (2)	C16—H16B	0.9600
N1—C17	1.4608 (19)	C16—H16C	0.9600
N1—C8	1.4827 (18)	C17—C18	1.511 (2)
C1—C2	1.327 (2)	C17—H17A	0.9700
C1—C8	1.503 (2)	C17—H17B	0.9700
C1—H1	0.9300	C18—C19	1.392 (2)
C2—C3	1.460 (2)	C18—C23	1.396 (2)
C2—H2	0.9300	C19—C20	1.388 (2)
C3—C4	1.337 (2)	C19—H19	0.9300
C3—H3	0.9300	C20—C21	1.380 (2)
C4—C9	1.483 (2)	C20—H20	0.9300
C4—C7	1.5216 (18)	C21—C22	1.381 (2)
C5—C6	1.356 (2)	C22—C23	1.386 (2)
C5—C13	1.443 (2)	C22—H22	0.9300
C5—C7	1.5352 (19)	C23—H23	0.9300
C6—C15	1.502 (2)
C9—O2—C10	114.76 (13)	O4—C12—H12A	109.5
C11—O4—C12	115.10 (12)	O4—C12—H12B	109.5
C13—O6—C14	115.84 (12)	H12A—C12—H12B	109.5
C15—O8—C16	115.57 (13)	O4—C12—H12C	109.5
C6—N1—C17	128.67 (13)	H12A—C12—H12C	109.5
C6—N1—C8	108.78 (11)	H12B—C12—H12C	109.5
C17—N1—C8	121.90 (12)	O5—C13—O6	122.55 (14)
C2—C1—C8	121.90 (13)	O5—C13—C5	124.43 (14)
C2—C1—H1	119.0	O6—C13—C5	112.99 (12)
C8—C1—H1	119.0	O6—C14—H14A	109.5
C1—C2—C3	120.89 (13)	O6—C14—H14B	109.5
C1—C2—H2	119.6	H14A—C14—H14B	109.5
C3—C2—H2	119.6	O6—C14—H14C	109.5
C4—C3—C2	122.09 (13)	H14A—C14—H14C	109.5
C4—C3—H3	119.0	H14B—C14—H14C	109.5
C2—C3—H3	119.0	O7—C15—O8	125.55 (14)
C3—C4—C9	121.48 (13)	O7—C15—C6	123.73 (14)
C3—C4—C7	121.00 (12)	O8—C15—C6	110.71 (12)
C9—C4—C7	117.52 (12)	O8—C16—H16A	109.5
C6—C5—C13	122.22 (13)	O8—C16—H16B	109.5
C6—C5—C7	107.38 (12)	H16A—C16—H16B	109.5
C13—C5—C7	130.01 (12)	O8—C16—H16C	109.5
N1—C6—C5	113.44 (13)	H16A—C16—H16C	109.5
N1—C6—C15	120.87 (13)	H16B—C16—H16C	109.5
C5—C6—C15	125.60 (14)	N1—C17—C18	110.66 (12)
C4—C7—C5	115.39 (11)	N1—C17—H17A	109.5
C4—C7—C11	112.18 (11)	C18—C17—H17A	109.5
C5—C7—C11	107.99 (11)	N1—C17—H17B	109.5
C4—C7—C8	112.51 (11)	C18—C17—H17B	109.5
C5—C7—C8	100.41 (11)	H17A—C17—H17B	108.1
C11—C7—C8	107.50 (11)	C19—C18—C23	118.75 (14)
N1—C8—C1	109.62 (12)	C19—C18—C17	120.20 (14)
N1—C8—C7	102.46 (11)	C23—C18—C17	120.86 (14)
C1—C8—C7	114.12 (12)	C20—C19—C18	121.05 (15)
N1—C8—H8	110.1	C20—C19—H19	119.5
C1—C8—H8	110.1	C18—C19—H19	119.5
C7—C8—H8	110.1	C21—C20—C19	118.71 (16)
O1—C9—O2	123.05 (14)	C21—C20—H20	120.6
O1—C9—C4	123.78 (14)	C19—C20—H20	120.6
O2—C9—C4	113.15 (12)	C20—C21—C22	121.74 (15)
O2—C10—H10A	109.5	C20—C21—Cl1	118.40 (13)
O2—C10—H10B	109.5	C22—C21—Cl1	119.85 (12)
H10A—C10—H10B	109.5	C21—C22—C23	118.97 (14)
O2—C10—H10C	109.5	C21—C22—H22	120.5
H10A—C10—H10C	109.5	C23—C22—H22	120.5
H10B—C10—H10C	109.5	C22—C23—C18	120.74 (15)
O3—C11—O4	124.28 (13)	C22—C23—H23	119.6
O3—C11—C7	124.82 (13)	C18—C23—H23	119.6
O4—C11—C7	110.71 (11)
C8—C1—C2—C3	0.4 (2)	C3—C4—C9—O1	155.02 (15)
C1—C2—C3—C4	10.3 (2)	C7—C4—C9—O1	−24.3 (2)
C2—C3—C4—C9	−176.68 (13)	C3—C4—C9—O2	−23.48 (19)
C2—C3—C4—C7	2.6 (2)	C7—C4—C9—O2	157.18 (12)
C17—N1—C6—C5	−162.44 (14)	C12—O4—C11—O3	5.4 (2)
C8—N1—C6—C5	8.31 (16)	C12—O4—C11—C7	−179.31 (12)
C17—N1—C6—C15	20.7 (2)	C4—C7—C11—O3	−120.62 (15)
C8—N1—C6—C15	−168.60 (12)	C5—C7—C11—O3	7.64 (19)
C13—C5—C6—N1	−176.27 (13)	C8—C7—C11—O3	115.19 (16)
C7—C5—C6—N1	10.27 (16)	C4—C7—C11—O4	64.08 (15)
C13—C5—C6—C15	0.5 (2)	C5—C7—C11—O4	−167.66 (11)
C7—C5—C6—C15	−172.99 (13)	C8—C7—C11—O4	−60.11 (14)
C3—C4—C7—C5	91.32 (16)	C14—O6—C13—O5	−0.8 (2)
C9—C4—C7—C5	−89.34 (15)	C14—O6—C13—C5	−178.73 (12)
C3—C4—C7—C11	−144.44 (13)	C6—C5—C13—O5	−0.9 (2)
C9—C4—C7—C11	34.90 (17)	C7—C5—C13—O5	170.93 (14)
C3—C4—C7—C8	−23.09 (18)	C6—C5—C13—O6	177.00 (12)
C9—C4—C7—C8	156.26 (12)	C7—C5—C13—O6	−11.2 (2)
C6—C5—C7—C4	−144.05 (12)	C16—O8—C15—O7	7.9 (2)
C13—C5—C7—C4	43.2 (2)	C16—O8—C15—C6	−172.97 (14)
C6—C5—C7—C11	89.54 (13)	N1—C6—C15—O7	81.1 (2)
C13—C5—C7—C11	−83.23 (17)	C5—C6—C15—O7	−95.4 (2)
C6—C5—C7—C8	−22.86 (14)	N1—C6—C15—O8	−98.03 (16)
C13—C5—C7—C8	164.37 (14)	C5—C6—C15—O8	85.46 (17)
C6—N1—C8—C1	99.12 (14)	C6—N1—C17—C18	108.34 (17)
C17—N1—C8—C1	−89.38 (16)	C8—N1—C17—C18	−61.33 (18)
C6—N1—C8—C7	−22.42 (14)	N1—C17—C18—C19	97.88 (17)
C17—N1—C8—C7	149.08 (13)	N1—C17—C18—C23	−77.16 (17)
C2—C1—C8—N1	−135.62 (15)	C23—C18—C19—C20	0.4 (2)
C2—C1—C8—C7	−21.4 (2)	C17—C18—C19—C20	−174.75 (15)
C4—C7—C8—N1	149.46 (11)	C18—C19—C20—C21	−1.7 (3)
C5—C7—C8—N1	26.23 (13)	C19—C20—C21—C22	1.6 (3)
C11—C7—C8—N1	−86.55 (12)	C19—C20—C21—Cl1	−178.26 (13)
C4—C7—C8—C1	31.05 (16)	C20—C21—C22—C23	0.0 (2)
C5—C7—C8—C1	−92.18 (13)	Cl1—C21—C22—C23	179.79 (12)
C11—C7—C8—C1	155.04 (12)	C21—C22—C23—C18	−1.4 (2)
C10—O2—C9—O1	−2.0 (2)	C19—C18—C23—C22	1.2 (2)
C10—O2—C9—C4	176.49 (13)	C17—C18—C23—C22	176.28 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O5^i	0.93	2.56	3.441 (2)	159
C3—H3···O3^ii	0.93	2.53	3.220 (2)	132
C16—H16A···O5^iii	0.96	2.51	3.269 (2)	136
C17—H17B···O5^i	0.97	2.53	3.390 (2)	148
C19—H19···O7^i	0.93	2.56	3.485 (2)	177

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