3-Ethyl-2-phenyl­sulfonyl-1,2,3,3a,10,10a,11,11a-octa­hydro-5H-pyrrolo[3,4:2′,3′]pyrrolo[1,5-b]isoquinolin-5-one

In the title mol­ecule, C₂₂H₂₄N₂O₃S, the fused pyridinone ring adopts a half-chair conformation while the pyrrolidine rings adopt envelope and twist conformations. C—H...O inter­actions link the mol­ecules into a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.001 Å
• Disorder in main residue
• R factor = 0.044
• wR factor = 0.131
• Data-to-parameter ratio = 44.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT301_ALERT_3_C Main Residue  Disorder .........................       3.00 Perc.

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

   0 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
   1 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

---

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

3-Ethyl-2-phenylsulfonyl-1,2,3,3a,10,10a,11,11a-octahydro- 5H-pyrrolo[3,4:2',3']pyrrolo[1,5-b]isoquinolin-5-one

Crystal data

C22H24N2O3S	F(000) = 840
Mr = 396.49	Dx = 1.383 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7955 reflections
a = 10.7021 (2) Å	θ = 2.2–43.5°
b = 11.8115 (2) Å	µ = 0.20 mm^−1
c = 15.7264 (3) Å	T = 100 K
β = 106.660 (1)°	Block, yellow
V = 1904.49 (6) Å^3	0.58 × 0.55 × 0.45 mm
Z = 4

Data collection

Bruker SMART APEX2 CCD diffractometer	11737 independent reflections
Radiation source: fine-focus sealed tube	9292 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 8.33 pixels mm^-1	θmax = 40.0°, θmin = 2.2°
ω scans	h = −19→19
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −18→21
Tmin = 0.890, Tmax = 0.917	l = −28→28
40101 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0592P)^2 + 0.5945P] where P = (Fo^2 + 2Fc^2)/3
11737 reflections	(Δ/σ)max = 0.001
262 parameters	Δρmax = 0.55 e Å^−3
7 restraints	Δρmin = −0.94 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	Occ. (<1)
S1	0.122829 (19)	0.679726 (18)	0.222115 (12)	0.01568 (4)
O1	0.06150 (7)	0.75641 (7)	0.15153 (4)	0.02251 (13)
O2	0.11433 (7)	0.55979 (6)	0.20688 (5)	0.02319 (13)
O3	0.33795 (7)	0.57132 (6)	0.53319 (5)	0.02572 (14)
N1	0.06049 (7)	0.70539 (6)	0.30275 (4)	0.01494 (11)
N2	0.2604 (5)	0.7479 (4)	0.4966 (3)	0.0117 (5)	0.50
N2A	0.2628 (5)	0.7484 (5)	0.4864 (3)	0.0279 (10)	0.50
C1	0.04348 (9)	0.82495 (7)	0.32505 (5)	0.01875 (13)
H1A	−0.0428	0.8537	0.2899	0.022*
H1B	0.1123	0.8730	0.3130	0.022*
C2	0.05405 (8)	0.82496 (7)	0.42485 (5)	0.01620 (12)
H2	−0.0339	0.8289	0.4350	0.019*
C3	0.12436 (7)	0.71334 (7)	0.46057 (5)	0.01482 (11)
H3	0.0906	0.6823	0.5089	0.018*	0.50
H3A	0.0983	0.6839	0.5098	0.018*	0.50
C4	0.09620 (7)	0.63044 (7)	0.38232 (5)	0.01371 (11)
H4	0.1777	0.5880	0.3839	0.016*
C5	0.14440 (8)	0.91804 (7)	0.47604 (6)	0.01750 (13)
H5A	0.1292	0.9319	0.5344	0.021*
H5B	0.1313	0.9897	0.4419	0.021*
C6	0.28137 (8)	0.87040 (7)	0.48735 (5)	0.01543 (12)
H6	0.3089	0.8850	0.4327	0.019*	0.50
H6A	0.3075	0.8907	0.4358	0.019*	0.50
C7	0.38606 (8)	0.91112 (8)	0.56898 (6)	0.01929 (14)
H7A	0.4087	0.9907	0.5604	0.023*
H7B	0.3524	0.9080	0.6214	0.023*
C8	0.50613 (8)	0.83827 (7)	0.58508 (5)	0.01705 (13)
C9	0.49159 (8)	0.72356 (7)	0.56271 (5)	0.01625 (12)
C10	0.35838 (8)	0.67342 (7)	0.52867 (5)	0.01556 (12)
C11	0.63166 (9)	0.88082 (8)	0.62269 (6)	0.02205 (15)
H11	0.6429	0.9580	0.6402	0.026*
C12	0.74033 (9)	0.81158 (9)	0.63476 (7)	0.02558 (18)
H12	0.8252	0.8417	0.6599	0.031*
C13	0.72513 (9)	0.69814 (9)	0.61005 (7)	0.02550 (17)
H13	0.7995	0.6512	0.6172	0.031*
C14	0.60051 (9)	0.65379 (8)	0.57484 (6)	0.02146 (15)
H14	0.5896	0.5760	0.5590	0.026*
C15	0.29003 (8)	0.71553 (7)	0.25948 (5)	0.01721 (13)
C16	0.33037 (9)	0.82220 (8)	0.24108 (7)	0.02233 (15)
H16	0.2691	0.8751	0.2073	0.027*
C17	0.46201 (10)	0.85062 (10)	0.27281 (8)	0.0295 (2)
H17	0.4911	0.9230	0.2601	0.035*
C18	0.55084 (10)	0.77294 (12)	0.32309 (8)	0.0321 (2)
H18	0.6401	0.7933	0.3457	0.039*
C19	0.51001 (10)	0.66601 (11)	0.34045 (7)	0.0298 (2)
H19	0.5713	0.6133	0.3744	0.036*
C20	0.37913 (9)	0.63622 (9)	0.30808 (7)	0.02290 (16)
H20	0.3507	0.5628	0.3189	0.027*
C21	−0.01279 (8)	0.54639 (7)	0.38050 (5)	0.01737 (13)
H21A	−0.0294	0.5005	0.3257	0.021*
H21B	0.0175	0.4943	0.4316	0.021*
C22	−0.14100 (9)	0.59989 (9)	0.38381 (7)	0.02276 (16)
H22A	−0.2046	0.5402	0.3838	0.034*
H22B	−0.1746	0.6486	0.3318	0.034*
H22C	−0.1262	0.6453	0.4380	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01894 (8)	0.01591 (9)	0.01317 (7)	−0.00133 (6)	0.00620 (6)	0.00022 (6)
O1	0.0233 (3)	0.0286 (3)	0.0155 (2)	0.0014 (2)	0.0053 (2)	0.0066 (2)
O2	0.0335 (3)	0.0179 (3)	0.0217 (3)	−0.0058 (2)	0.0135 (3)	−0.0052 (2)
O3	0.0279 (3)	0.0185 (3)	0.0289 (3)	0.0003 (2)	0.0052 (3)	0.0018 (3)
N1	0.0176 (2)	0.0147 (3)	0.0132 (2)	0.0011 (2)	0.00556 (19)	0.0012 (2)
N2	0.0149 (9)	0.0104 (11)	0.0102 (5)	−0.0011 (7)	0.0040 (6)	−0.0003 (5)
N2A	0.0185 (13)	0.0110 (12)	0.046 (2)	0.0018 (9)	−0.0043 (14)	0.0041 (15)
C1	0.0234 (3)	0.0156 (3)	0.0162 (3)	0.0053 (3)	0.0040 (3)	0.0018 (2)
C2	0.0173 (3)	0.0146 (3)	0.0166 (3)	0.0028 (2)	0.0048 (2)	−0.0003 (2)
C3	0.0167 (3)	0.0129 (3)	0.0143 (3)	0.0004 (2)	0.0036 (2)	−0.0004 (2)
C4	0.0155 (2)	0.0134 (3)	0.0128 (2)	0.0003 (2)	0.0050 (2)	0.0005 (2)
C5	0.0210 (3)	0.0131 (3)	0.0185 (3)	0.0025 (2)	0.0058 (2)	−0.0004 (2)
C6	0.0196 (3)	0.0111 (3)	0.0156 (3)	0.0005 (2)	0.0051 (2)	0.0011 (2)
C7	0.0209 (3)	0.0158 (3)	0.0196 (3)	−0.0010 (3)	0.0033 (3)	−0.0032 (3)
C8	0.0189 (3)	0.0153 (3)	0.0161 (3)	−0.0023 (2)	0.0035 (2)	0.0009 (2)
C9	0.0176 (3)	0.0147 (3)	0.0150 (3)	−0.0004 (2)	0.0024 (2)	0.0012 (2)
C10	0.0178 (3)	0.0119 (3)	0.0156 (3)	0.0003 (2)	0.0025 (2)	0.0009 (2)
C11	0.0208 (3)	0.0195 (4)	0.0237 (4)	−0.0054 (3)	0.0028 (3)	0.0005 (3)
C12	0.0188 (3)	0.0279 (5)	0.0272 (4)	−0.0040 (3)	0.0021 (3)	0.0024 (3)
C13	0.0186 (3)	0.0284 (5)	0.0264 (4)	0.0033 (3)	0.0016 (3)	0.0012 (3)
C14	0.0199 (3)	0.0192 (4)	0.0221 (3)	0.0035 (3)	0.0010 (3)	0.0005 (3)
C15	0.0182 (3)	0.0162 (3)	0.0189 (3)	0.0015 (2)	0.0080 (2)	0.0008 (3)
C16	0.0215 (3)	0.0174 (4)	0.0303 (4)	−0.0002 (3)	0.0108 (3)	0.0013 (3)
C17	0.0244 (4)	0.0258 (5)	0.0419 (6)	−0.0060 (3)	0.0149 (4)	−0.0069 (4)
C18	0.0194 (3)	0.0422 (6)	0.0357 (5)	−0.0017 (4)	0.0096 (3)	−0.0088 (5)
C19	0.0209 (4)	0.0409 (6)	0.0283 (4)	0.0098 (4)	0.0084 (3)	0.0036 (4)
C20	0.0226 (3)	0.0235 (4)	0.0252 (4)	0.0072 (3)	0.0111 (3)	0.0056 (3)
C21	0.0203 (3)	0.0162 (3)	0.0171 (3)	−0.0035 (2)	0.0077 (2)	−0.0013 (2)
C22	0.0182 (3)	0.0260 (4)	0.0257 (4)	−0.0033 (3)	0.0090 (3)	−0.0010 (3)

Geometric parameters (Å, º)

S1—O2	1.4353 (8)	C7—H7A	0.99
S1—O1	1.4372 (7)	C7—H7B	0.99
S1—N1	1.6218 (7)	C8—C11	1.3971 (12)
S1—C15	1.7673 (8)	C8—C9	1.3972 (12)
O3—C10	1.2313 (11)	C9—C14	1.3952 (12)
N1—C1	1.4789 (11)	C9—C10	1.4941 (11)
N1—C4	1.4904 (10)	C11—C12	1.3896 (14)
N2—C10	1.351 (5)	C11—H11	0.95
N2—C3	1.460 (5)	C12—C13	1.3915 (16)
N2—C6	1.478 (5)	C12—H12	0.95
N2A—C10	1.372 (5)	C13—C14	1.3915 (13)
N2A—C6	1.454 (6)	C13—H13	0.95
N2A—C3	1.479 (6)	C14—H14	0.95
C1—C2	1.5408 (12)	C15—C16	1.3889 (13)
C1—H1A	0.99	C15—C20	1.3976 (12)
C1—H1B	0.99	C16—C17	1.3940 (14)
C2—C5	1.5315 (12)	C16—H16	0.95
C2—C3	1.5420 (11)	C17—C18	1.3928 (18)
C2—H2	1.00	C17—H17	0.95
C3—C4	1.5335 (11)	C18—C19	1.3889 (19)
C3—H3	1.00	C18—H18	0.95
C3—H3A	0.96	C19—C20	1.3914 (15)
C4—C21	1.5257 (11)	C19—H19	0.95
C4—H4	1.00	C20—H20	0.95
C5—C6	1.5322 (11)	C21—C22	1.5251 (12)
C5—H5A	0.99	C21—H21A	0.99
C5—H5B	0.99	C21—H21B	0.99
C6—C7	1.5198 (11)	C22—H22A	0.98
C6—H6	1.00	C22—H22B	0.98
C6—H6A	0.96	C22—H22C	0.98
C7—C8	1.5064 (12)
O2—S1—O1	120.00 (5)	N2—C6—H6A	114.6
O2—S1—N1	107.12 (4)	C7—C6—H6A	108.1
O1—S1—N1	106.68 (4)	C5—C6—H6A	108.1
O2—S1—C15	107.54 (4)	C8—C7—C6	110.36 (7)
O1—S1—C15	107.50 (4)	C8—C7—H7A	109.6
N1—S1—C15	107.43 (4)	C6—C7—H7A	109.6
C1—N1—C4	112.79 (6)	C8—C7—H7B	109.6
C1—N1—S1	118.04 (6)	C6—C7—H7B	109.6
C4—N1—S1	118.78 (5)	H7A—C7—H7B	108.1
C10—N2—C3	123.0 (4)	C11—C8—C9	118.66 (8)
C10—N2—C6	123.4 (4)	C11—C8—C7	122.42 (8)
C3—N2—C6	113.5 (3)	C9—C8—C7	118.92 (7)
C10—N2A—C6	123.6 (4)	C14—C9—C8	120.66 (8)
C10—N2A—C3	120.1 (4)	C14—C9—C10	119.26 (8)
C6—N2A—C3	113.8 (4)	C8—C9—C10	120.03 (7)
N1—C1—C2	105.28 (6)	O3—C10—N2	121.8 (2)
N1—C1—H1A	110.7	O3—C10—N2A	122.7 (3)
C2—C1—H1A	110.7	O3—C10—C9	122.31 (7)
N1—C1—H1B	110.7	N2—C10—C9	115.8 (2)
C2—C1—H1B	110.7	N2A—C10—C9	114.8 (3)
H1A—C1—H1B	108.8	C12—C11—C8	120.77 (9)
C5—C2—C1	112.73 (7)	C12—C11—H11	119.6
C5—C2—C3	104.70 (6)	C8—C11—H11	119.6
C1—C2—C3	104.88 (6)	C11—C12—C13	120.15 (9)
C5—C2—H2	111.4	C11—C12—H12	119.9
C1—C2—H2	111.4	C13—C12—H12	119.9
C3—C2—H2	111.4	C14—C13—C12	119.71 (9)
N2—C3—C4	115.73 (17)	C14—C13—H13	120.1
N2A—C3—C4	110.5 (2)	C12—C13—H13	120.1
N2—C3—C2	103.3 (2)	C13—C14—C9	119.99 (9)
N2A—C3—C2	101.9 (2)	C13—C14—H14	120.0
C4—C3—C2	106.88 (6)	C9—C14—H14	120.0
N2—C3—H3	110.2	C16—C15—C20	121.19 (8)
N2A—C3—H3	116.5	C16—C15—S1	119.56 (7)
C4—C3—H3	110.2	C20—C15—S1	119.24 (7)
C2—C3—H3	110.2	C15—C16—C17	119.11 (9)
N2—C3—H3A	106.0	C15—C16—H16	120.4
N2A—C3—H3A	112.3	C17—C16—H16	120.4
C4—C3—H3A	112.3	C18—C17—C16	119.99 (10)
C2—C3—H3A	112.3	C18—C17—H17	120.0
N1—C4—C21	111.11 (6)	C16—C17—H17	120.0
N1—C4—C3	103.81 (6)	C19—C18—C17	120.57 (10)
C21—C4—C3	113.81 (6)	C19—C18—H18	119.7
N1—C4—H4	109.3	C17—C18—H18	119.7
C21—C4—H4	109.3	C18—C19—C20	119.90 (10)
C3—C4—H4	109.3	C18—C19—H19	120.1
C2—C5—C6	103.66 (6)	C20—C19—H19	120.1
C2—C5—H5A	111.0	C19—C20—C15	119.21 (10)
C6—C5—H5A	111.0	C19—C20—H20	120.4
C2—C5—H5B	111.0	C15—C20—H20	120.4
C6—C5—H5B	111.0	C22—C21—C4	114.85 (7)
H5A—C5—H5B	109.0	C22—C21—H21A	108.6
N2A—C6—C7	112.8 (2)	C4—C21—H21A	108.6
N2—C6—C7	108.85 (19)	C22—C21—H21B	108.6
N2A—C6—C5	103.8 (2)	C4—C21—H21B	108.6
N2—C6—C5	101.75 (19)	H21A—C21—H21B	107.5
C7—C6—C5	115.52 (7)	C21—C22—H22A	109.5
N2A—C6—H6	103.6	C21—C22—H22B	109.5
N2—C6—H6	110.1	H22A—C22—H22B	109.5
C7—C6—H6	110.1	C21—C22—H22C	109.5
C5—C6—H6	110.1	H22A—C22—H22C	109.5
N2A—C6—H6A	108.1	H22B—C22—H22C	109.5
O2—S1—N1—C1	−173.15 (6)	C2—C5—C6—N2	−33.83 (16)
O1—S1—N1—C1	−43.48 (7)	C2—C5—C6—C7	−151.53 (7)
C15—S1—N1—C1	71.55 (7)	N2A—C6—C7—C8	46.8 (2)
O2—S1—N1—C4	44.33 (7)	N2—C6—C7—C8	52.37 (18)
O1—S1—N1—C4	174.01 (6)	C5—C6—C7—C8	166.03 (7)
C15—S1—N1—C4	−70.96 (7)	C6—C7—C8—C11	148.04 (8)
C4—N1—C1—C2	−6.54 (9)	C6—C7—C8—C9	−32.81 (11)
S1—N1—C1—C2	−151.19 (6)	C11—C8—C9—C14	−2.19 (12)
N1—C1—C2—C5	132.95 (7)	C7—C8—C9—C14	178.62 (8)
N1—C1—C2—C3	19.63 (8)	C11—C8—C9—C10	175.46 (8)
C10—N2—C3—N2A	−96 (4)	C7—C8—C9—C10	−3.73 (11)
C6—N2—C3—N2A	79 (4)	C3—N2—C10—O3	−3.3 (4)
C10—N2—C3—C4	−58.1 (3)	C6—N2—C10—O3	−177.90 (18)
C6—N2—C3—C4	116.9 (2)	C3—N2—C10—N2A	96 (4)
C10—N2—C3—C2	−174.6 (2)	C6—N2—C10—N2A	−79 (4)
C6—N2—C3—C2	0.5 (2)	C3—N2—C10—C9	179.86 (19)
C10—N2A—C3—N2	72 (4)	C6—N2—C10—C9	5.3 (3)
C6—N2A—C3—N2	−91 (4)	C6—N2A—C10—O3	174.0 (3)
C10—N2A—C3—C4	−72.0 (4)	C3—N2A—C10—O3	12.9 (5)
C6—N2A—C3—C4	125.2 (3)	C6—N2A—C10—N2	89 (4)
C10—N2A—C3—C2	174.7 (3)	C3—N2A—C10—N2	−72 (4)
C6—N2A—C3—C2	11.9 (3)	C6—N2A—C10—C9	−10.6 (5)
C5—C2—C3—N2	−22.19 (16)	C3—N2A—C10—C9	−171.6 (3)
C1—C2—C3—N2	96.70 (15)	C14—C9—C10—O3	20.09 (13)
C5—C2—C3—N2A	−28.8 (2)	C8—C9—C10—O3	−157.60 (9)
C1—C2—C3—N2A	90.1 (2)	C14—C9—C10—N2	−163.13 (17)
C5—C2—C3—C4	−144.74 (6)	C8—C9—C10—N2	19.18 (19)
C1—C2—C3—C4	−25.85 (8)	C14—C9—C10—N2A	−155.4 (2)
C1—N1—C4—C21	113.35 (7)	C8—C9—C10—N2A	27.0 (3)
S1—N1—C4—C21	−102.29 (7)	C9—C8—C11—C12	2.26 (14)
C1—N1—C4—C3	−9.37 (8)	C7—C8—C11—C12	−178.58 (9)
S1—N1—C4—C3	134.99 (6)	C8—C11—C12—C13	−0.55 (15)
N2—C3—C4—N1	−92.8 (2)	C11—C12—C13—C14	−1.27 (16)
N2A—C3—C4—N1	−88.5 (2)	C12—C13—C14—C9	1.33 (15)
C2—C3—C4—N1	21.60 (7)	C8—C9—C14—C13	0.41 (13)
N2—C3—C4—C21	146.3 (2)	C10—C9—C14—C13	−177.25 (8)
N2A—C3—C4—C21	150.6 (2)	O2—S1—C15—C16	150.31 (7)
C2—C3—C4—C21	−99.32 (8)	O1—S1—C15—C16	19.81 (9)
C1—C2—C5—C6	−78.11 (8)	N1—S1—C15—C16	−94.67 (8)
C3—C2—C5—C6	35.32 (8)	O2—S1—C15—C20	−30.50 (8)
C10—N2A—C6—N2	−80 (4)	O1—S1—C15—C20	−161.00 (7)
C3—N2A—C6—N2	82 (3)	N1—S1—C15—C20	84.52 (8)
C10—N2A—C6—C7	−26.5 (5)	C20—C15—C16—C17	−0.81 (14)
C3—N2A—C6—C7	135.5 (3)	S1—C15—C16—C17	178.37 (8)
C10—N2A—C6—C5	−152.4 (3)	C15—C16—C17—C18	−0.74 (16)
C3—N2A—C6—C5	9.7 (4)	C16—C17—C18—C19	1.41 (17)
C10—N2—C6—N2A	87 (3)	C17—C18—C19—C20	−0.53 (17)
C3—N2—C6—N2A	−88 (4)	C18—C19—C20—C15	−0.99 (15)
C10—N2—C6—C7	−41.4 (3)	C16—C15—C20—C19	1.68 (14)
C3—N2—C6—C7	143.58 (18)	S1—C15—C20—C19	−177.50 (8)
C10—N2—C6—C5	−163.8 (2)	N1—C4—C21—C22	−62.92 (9)
C3—N2—C6—C5	21.2 (2)	C3—C4—C21—C22	53.83 (9)
C2—C5—C6—N2A	−27.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2^i	0.99	2.56	3.2113 (11)	124
C3—H3···O1^ii	1.00	2.46	3.2798 (10)	139
C4—H4···O3	1.00	2.49	3.0481 (11)	115
C14—H14···O3^iii	0.95	2.52	3.3214 (12)	141
C16—H16···O1	0.95	2.56	2.9229 (13)	103
C22—H22A···O3^iv	0.98	2.56	3.4371 (13)	149

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