(3aS,5aR,10aS,11aR)-2,2-Di­methyl-3a,9,10,10a,11,11a-hexa­hydro-5aH-1,3-dioxolo­[4,5:3′,4′]­furo­[2′,3′-f]­indolizin-8(4H)-one

In the crystal structure of the title compound, C₁₃H₁₉NO₄, there are two mol­ecules in the asymmetric unit. The crystal which was used for collecting intensity data was twinned. The furoindolizine ring system adopts a fused envelope–chair–envelope conformation. The packing is stabilized by intermolecular C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 183 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.082
• Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size .......       0.85 mm
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.82 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.41 Ratio

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C13 H19 N O4

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           32.94
           From the CIF: _reflns_number_total               4637
           Count of symmetry unique reflns         4823
           Completeness (_total/calc)             96.14%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

(3aS,5aR,10aS,11aR)-2,2-Dimethyl-3a,9,10,10a,11,11a-hexahydro- 5aH-1,3-dioxolo[4,5:3',4']furo[2',3'-f]indolizin-8(4H)-one

Crystal data

C13H19NO4	F(000) = 544
Mr = 253.29	Dx = 1.343 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 5.9465 (1) Å	Cell parameters from 6898 reflections
b = 17.7167 (3) Å	θ = 3.2–30.9°
c = 11.8918 (2) Å	µ = 0.10 mm^−1
β = 90.037 (1)°	T = 183 K
V = 1252.83 (4) Å^3	Needle, colorless
Z = 4	0.85 × 0.10 × 0.08 mm

Data collection

Siemens SMART CCD diffractometer	4637 independent reflections
Radiation source: fine-focus sealed tube	4190 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
ω scans	θmax = 32.9°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −9→9
Tmin = 0.920, Tmax = 0.992	k = −27→26
22580 measured reflections	l = −17→18

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.082	Only H-atom displacement parameters refined
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0447P)^2 + 0.0464P] where P = (Fo^2 + 2Fc^2)/3
4637 reflections	(Δ/σ)max = 0.001
368 parameters	Δρmax = 0.21 e Å^−3
1 restraint	Δρmin = −0.18 e Å^−3

Special details

Refinement. Data were collected at 183 K using a Siemens SMART CCD diffractometer equipped witha Siemens LT-2 A low temperature device. A sphere of reciprocal space was scanned by 0.3° steps in ω with a crystal–to–detector distance of 3.97 cm. Preliminary orientation matrix was obtained from the first 100 frames using SMART (Siemens, 1995). Exposure time was 20 sec per frame. The collected frames were integrated using the preliminary orientation matrix which was updated every 100 frames. Final cell parameters were obtained by refinement on the position of 6898 reflections with I>10σ(I) after integration of all the frames data using SAINT(Siemens, 1995). The data were empirically corrected for absorption and other effects using SADABS (Sheldrick, 2002) based on the multiscan method of Blessing (1995). The structure was solved by direct method (Bruker, 1997) and refined by full-matrix least squares on all F² data using SHELXL97 (Sheldrick, 1997).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.9206 (3)	0.64388 (9)	0.92727 (14)	0.0299 (3)
O2	0.9283 (4)	0.57366 (14)	0.50274 (15)	0.0484 (5)
O3	0.4540 (3)	0.58764 (8)	1.06008 (12)	0.0294 (3)
O4	0.7013 (3)	0.50139 (9)	0.98841 (13)	0.0299 (3)
N1	0.7057 (3)	0.56903 (11)	0.65957 (15)	0.0275 (4)
C1	0.7115 (4)	0.67844 (12)	0.96419 (19)	0.0275 (4)
H1A	0.6738	0.7221	0.9158	0.032 (7)*
H1B	0.7256	0.6962	1.0428	0.029 (7)*
C2	0.5281 (4)	0.61781 (11)	0.95537 (17)	0.0234 (4)
H2	0.3980	0.6363	0.9098	0.038 (8)*
C3	0.6461 (3)	0.55059 (11)	0.89650 (16)	0.0222 (3)
C4	0.5104 (4)	0.50483 (11)	0.81155 (18)	0.0248 (4)
H4A	0.5839	0.4552	0.8013	0.027 (6)*
H4B	0.3586	0.4956	0.8428	0.039 (8)*
C5	0.4860 (4)	0.54238 (12)	0.69740 (18)	0.0267 (4)
H5	0.3780	0.5855	0.7022	0.035 (7)*
C6	0.4157 (5)	0.48807 (15)	0.6018 (2)	0.0376 (6)
H6A	0.4443	0.4350	0.6234	0.050 (9)*
H6B	0.2541	0.4940	0.5839	0.046 (9)*
C7	0.5606 (5)	0.51042 (15)	0.50131 (19)	0.0374 (5)
H7A	0.6142	0.4651	0.4607	0.063 (11)*
H7B	0.4744	0.5425	0.4485	0.063 (11)*
C8	0.7566 (4)	0.55379 (14)	0.55085 (18)	0.0315 (4)
C9	0.8283 (4)	0.62005 (12)	0.73153 (18)	0.0281 (4)
H9A	0.7447	0.6682	0.7381	0.017 (6)*
H9B	0.9767	0.6311	0.6976	0.047 (9)*
C10	0.8621 (3)	0.58576 (13)	0.84957 (18)	0.0251 (4)
H10	0.9841	0.5469	0.8472	0.022 (6)*
C11	0.5965 (4)	0.52572 (12)	1.09060 (18)	0.0288 (4)
C12	0.4467 (5)	0.46353 (15)	1.1358 (2)	0.0386 (6)
H12A	0.3291	0.4520	1.0807	0.046 (9)*
H12B	0.3771	0.4802	1.2063	0.082 (14)*
H12C	0.5370	0.4182	1.1498	0.066 (11)*
C13	0.7779 (5)	0.55064 (16)	1.1732 (2)	0.0383 (5)
H13A	0.8652	0.5066	1.1974	0.049 (9)*
H13B	0.7072	0.5743	1.2388	0.044 (8)*
H13C	0.8779	0.5871	1.1366	0.050 (9)*
O5	1.4318 (3)	0.69273 (9)	0.33766 (15)	0.0324 (3)
O6	1.4017 (4)	0.76190 (12)	0.76339 (16)	0.0469 (5)
O7	0.9630 (3)	0.74030 (8)	0.19978 (13)	0.0278 (3)
O8	1.2014 (3)	0.83107 (9)	0.26841 (12)	0.0293 (3)
N2	1.1992 (3)	0.77089 (11)	0.60012 (15)	0.0280 (4)
C14	1.2286 (4)	0.65535 (12)	0.30098 (19)	0.0281 (4)
H14A	1.1947	0.6120	0.3506	0.043 (9)*
H14B	1.2466	0.6365	0.2231	0.039 (8)*
C15	1.0378 (4)	0.71366 (11)	0.30636 (17)	0.0229 (4)
H15	0.9090	0.6944	0.3522	0.031 (7)*
C16	1.1465 (3)	0.78348 (11)	0.36218 (17)	0.0228 (4)
C17	1.0040 (4)	0.82996 (11)	0.44336 (17)	0.0256 (4)
H17A	0.8529	0.8373	0.4101	0.022 (6)*
H17B	1.0736	0.8804	0.4523	0.025 (6)*
C18	0.9777 (4)	0.79384 (12)	0.55952 (18)	0.0272 (4)
H18	0.8757	0.7491	0.5549	0.030 (7)*
C19	0.8971 (5)	0.84802 (17)	0.6527 (2)	0.0405 (6)
H19A	0.9294	0.9011	0.6325	0.061 (11)*
H19B	0.7335	0.8424	0.6657	0.064 (11)*
C20	1.0305 (5)	0.82445 (15)	0.7570 (2)	0.0361 (5)
H20A	1.0770	0.8692	0.8010	0.055 (10)*
H20B	0.9396	0.7910	0.8057	0.097 (15)*
C21	1.2346 (4)	0.78284 (14)	0.71150 (19)	0.0331 (5)
C22	1.3297 (4)	0.71904 (13)	0.53083 (18)	0.0279 (4)
H22A	1.2502	0.6701	0.5255	0.070 (12)*
H22B	1.4778	0.7100	0.5664	0.041 (8)*
C23	1.3640 (4)	0.75154 (13)	0.41246 (18)	0.0257 (4)
H23	1.4818	0.7918	0.4146	0.022 (6)*
C24	1.0986 (4)	0.80329 (11)	0.16642 (17)	0.0240 (4)
C25	1.2801 (5)	0.78075 (15)	0.0852 (2)	0.0362 (5)
H25A	1.3787	0.7433	0.1206	0.041 (8)*
H25B	1.3683	0.8253	0.0643	0.046 (9)*
H25C	1.2115	0.7589	0.0176	0.057 (10)*
C26	0.9411 (5)	0.86188 (14)	0.1180 (2)	0.0367 (6)
H26A	0.8671	0.8414	0.0510	0.037 (7)*
H26B	1.0268	0.9071	0.0975	0.022 (6)*
H26C	0.8272	0.8752	0.1742	0.067 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0239 (7)	0.0322 (7)	0.0335 (7)	−0.0043 (7)	−0.0042 (6)	−0.0056 (6)
O2	0.0464 (11)	0.0657 (13)	0.0331 (9)	−0.0068 (10)	0.0114 (8)	−0.0002 (9)
O3	0.0330 (8)	0.0275 (7)	0.0277 (7)	0.0067 (7)	0.0086 (6)	0.0020 (6)
O4	0.0356 (8)	0.0277 (7)	0.0265 (7)	0.0095 (7)	0.0039 (6)	0.0040 (6)
N1	0.0270 (9)	0.0289 (9)	0.0267 (8)	−0.0030 (8)	0.0034 (7)	−0.0011 (7)
C1	0.0302 (10)	0.0236 (9)	0.0286 (10)	−0.0001 (8)	−0.0017 (8)	−0.0027 (7)
C2	0.0254 (10)	0.0212 (8)	0.0235 (8)	0.0017 (8)	0.0017 (7)	−0.0010 (7)
C3	0.0216 (9)	0.0199 (8)	0.0251 (9)	0.0007 (7)	0.0013 (7)	−0.0001 (7)
C4	0.0221 (9)	0.0208 (8)	0.0314 (10)	−0.0041 (8)	0.0022 (8)	0.0000 (7)
C5	0.0221 (9)	0.0256 (9)	0.0324 (10)	−0.0023 (8)	−0.0024 (8)	−0.0002 (8)
C6	0.0350 (13)	0.0396 (14)	0.0383 (12)	−0.0087 (11)	−0.0080 (10)	−0.0059 (10)
C7	0.0454 (14)	0.0363 (12)	0.0306 (11)	0.0058 (11)	−0.0091 (10)	−0.0041 (9)
C8	0.0386 (12)	0.0307 (10)	0.0252 (9)	0.0044 (9)	0.0003 (9)	0.0033 (8)
C9	0.0266 (10)	0.0270 (9)	0.0308 (10)	−0.0060 (8)	0.0036 (8)	0.0012 (8)
C10	0.0187 (8)	0.0262 (9)	0.0305 (9)	−0.0021 (8)	0.0003 (7)	−0.0016 (8)
C11	0.0333 (11)	0.0249 (9)	0.0281 (9)	0.0025 (8)	0.0021 (9)	0.0020 (7)
C12	0.0431 (14)	0.0337 (12)	0.0389 (12)	−0.0038 (11)	0.0083 (11)	0.0064 (10)
C13	0.0419 (14)	0.0369 (12)	0.0360 (12)	−0.0004 (11)	−0.0068 (11)	0.0019 (10)
O5	0.0246 (7)	0.0378 (8)	0.0349 (8)	0.0072 (7)	0.0053 (7)	−0.0028 (7)
O6	0.0542 (12)	0.0518 (11)	0.0348 (9)	0.0032 (10)	−0.0152 (9)	−0.0010 (8)
O7	0.0321 (8)	0.0243 (6)	0.0269 (7)	−0.0061 (6)	−0.0051 (6)	0.0039 (5)
O8	0.0350 (8)	0.0274 (7)	0.0256 (7)	−0.0121 (7)	−0.0015 (6)	0.0039 (6)
N2	0.0249 (9)	0.0353 (10)	0.0239 (8)	0.0028 (8)	−0.0005 (7)	−0.0015 (7)
C14	0.0328 (11)	0.0238 (9)	0.0277 (9)	0.0049 (8)	0.0022 (8)	−0.0002 (8)
C15	0.0251 (9)	0.0203 (7)	0.0233 (8)	−0.0027 (7)	0.0011 (7)	0.0006 (7)
C16	0.0202 (8)	0.0219 (8)	0.0262 (9)	−0.0030 (8)	−0.0007 (7)	0.0021 (7)
C17	0.0232 (9)	0.0238 (8)	0.0297 (9)	0.0022 (8)	−0.0009 (8)	−0.0022 (8)
C18	0.0211 (9)	0.0310 (10)	0.0293 (9)	0.0001 (8)	0.0015 (8)	−0.0031 (8)
C19	0.0382 (13)	0.0477 (15)	0.0357 (12)	0.0059 (12)	0.0091 (11)	−0.0100 (11)
C20	0.0430 (13)	0.0359 (11)	0.0295 (10)	−0.0070 (11)	0.0051 (9)	−0.0063 (9)
C21	0.0374 (11)	0.0307 (10)	0.0311 (10)	−0.0073 (10)	−0.0013 (9)	−0.0014 (9)
C22	0.0240 (10)	0.0318 (10)	0.0279 (10)	0.0054 (8)	−0.0024 (8)	−0.0005 (8)
C23	0.0192 (8)	0.0299 (9)	0.0280 (9)	0.0001 (8)	0.0002 (7)	0.0010 (8)
C24	0.0264 (10)	0.0206 (8)	0.0251 (9)	−0.0003 (7)	−0.0012 (8)	0.0018 (7)
C25	0.0397 (13)	0.0376 (12)	0.0314 (11)	0.0010 (11)	0.0073 (10)	0.0000 (9)
C26	0.0366 (13)	0.0245 (10)	0.0490 (14)	0.0011 (9)	−0.0069 (11)	0.0085 (9)

Geometric parameters (Å, º)

O1—C10	1.426 (3)	O5—C23	1.428 (3)
O1—C1	1.454 (3)	O5—C14	1.445 (3)
O2—C8	1.222 (3)	O6—C21	1.227 (3)
O3—C2	1.425 (2)	O7—C15	1.423 (3)
O3—C11	1.433 (3)	O7—C24	1.433 (3)
O4—C11	1.432 (3)	O8—C16	1.436 (2)
O4—C3	1.436 (2)	O8—C24	1.444 (2)
N1—C8	1.355 (3)	N2—C21	1.358 (3)
N1—C9	1.442 (3)	N2—C22	1.458 (3)
N1—C5	1.461 (3)	N2—C18	1.460 (3)
C1—C2	1.534 (3)	C14—C15	1.536 (3)
C1—H1A	0.990	C14—H14A	0.990
C1—H1B	0.990	C14—H14B	0.990
C2—C3	1.550 (3)	C15—C16	1.545 (3)
C2—H2	1.000	C15—H15	1.000
C3—C4	1.526 (3)	C16—C17	1.526 (3)
C3—C10	1.533 (3)	C16—C23	1.533 (3)
C4—C5	1.519 (3)	C17—C18	1.530 (3)
C4—H4A	0.990	C17—H17A	0.990
C4—H4B	0.990	C17—H17B	0.990
C5—C6	1.547 (3)	C18—C19	1.543 (3)
C5—H5	1.000	C18—H18	1.000
C6—C7	1.526 (4)	C19—C20	1.529 (4)
C6—H6A	0.990	C19—H19A	0.990
C6—H6B	0.990	C19—H19B	0.990
C7—C8	1.515 (4)	C20—C21	1.519 (4)
C7—H7A	0.990	C20—H20A	0.990
C7—H7B	0.990	C20—H20B	0.990
C9—C10	1.543 (3)	C22—C23	1.535 (3)
C9—H9A	0.990	C22—H22A	0.990
C9—H9B	0.990	C22—H22B	0.990
C10—H10	1.000	C23—H23	1.000
C11—C12	1.516 (3)	C24—C25	1.503 (3)
C11—C13	1.524 (3)	C24—C26	1.512 (3)
C12—H12A	0.980	C25—H25A	0.980
C12—H12B	0.980	C25—H25B	0.980
C12—H12C	0.980	C25—H25C	0.980
C13—H13A	0.980	C26—H26A	0.980
C13—H13B	0.980	C26—H26B	0.980
C13—H13C	0.980	C26—H26C	0.980
C10—O1—C1	106.96 (16)	C23—O5—C14	106.61 (16)
C2—O3—C11	109.00 (15)	C15—O7—C24	109.21 (15)
C11—O4—C3	111.34 (15)	C16—O8—C24	110.85 (15)
C8—N1—C9	125.3 (2)	C21—N2—C22	124.6 (2)
C8—N1—C5	115.5 (2)	C21—N2—C18	114.72 (19)
C9—N1—C5	118.15 (17)	C22—N2—C18	117.96 (16)
O1—C1—C2	107.00 (16)	O5—C14—C15	107.27 (16)
O1—C1—H1A	110.3	O5—C14—H14A	110.3
C2—C1—H1A	110.3	C15—C14—H14A	110.3
O1—C1—H1B	110.3	O5—C14—H14B	110.3
C2—C1—H1B	110.3	C15—C14—H14B	110.3
H1A—C1—H1B	108.6	H14A—C14—H14B	108.5
O3—C2—C1	115.02 (18)	O7—C15—C14	114.60 (17)
O3—C2—C3	104.28 (15)	O7—C15—C16	104.33 (15)
C1—C2—C3	104.30 (17)	C14—C15—C16	104.32 (17)
O3—C2—H2	110.9	O7—C15—H15	111.1
C1—C2—H2	110.9	C14—C15—H15	111.1
C3—C2—H2	110.9	C16—C15—H15	111.1
O4—C3—C4	107.58 (16)	O8—C16—C17	107.52 (16)
O4—C3—C10	109.43 (16)	O8—C16—C23	109.14 (17)
C4—C3—C10	114.70 (16)	C17—C16—C23	114.91 (17)
O4—C3—C2	103.05 (15)	O8—C16—C15	103.40 (15)
C4—C3—C2	117.91 (16)	C17—C16—C15	118.10 (16)
C10—C3—C2	103.40 (16)	C23—C16—C15	102.99 (16)
C5—C4—C3	114.17 (16)	C16—C17—C18	113.73 (16)
C5—C4—H4A	108.7	C16—C17—H17A	108.8
C3—C4—H4A	108.7	C18—C17—H17A	108.8
C5—C4—H4B	108.7	C16—C17—H17B	108.8
C3—C4—H4B	108.7	C18—C17—H17B	108.8
H4A—C4—H4B	107.6	H17A—C17—H17B	107.7
N1—C5—C4	109.38 (18)	N2—C18—C17	108.80 (17)
N1—C5—C6	102.45 (19)	N2—C18—C19	102.50 (18)
C4—C5—C6	114.23 (18)	C17—C18—C19	114.9 (2)
N1—C5—H5	110.2	N2—C18—H18	110.1
C4—C5—H5	110.2	C17—C18—H18	110.1
C6—C5—H5	110.2	C19—C18—H18	110.1
C7—C6—C5	105.2 (2)	C20—C19—C18	104.5 (2)
C7—C6—H6A	110.7	C20—C19—H19A	110.8
C5—C6—H6A	110.7	C18—C19—H19A	110.8
C7—C6—H6B	110.7	C20—C19—H19B	110.8
C5—C6—H6B	110.7	C18—C19—H19B	110.8
H6A—C6—H6B	108.8	H19A—C19—H19B	108.9
C8—C7—C6	105.18 (19)	C21—C20—C19	104.96 (19)
C8—C7—H7A	110.7	C21—C20—H20A	110.8
C6—C7—H7A	110.7	C19—C20—H20A	110.8
C8—C7—H7B	110.7	C21—C20—H20B	110.8
C6—C7—H7B	110.7	C19—C20—H20B	110.8
H7A—C7—H7B	108.8	H20A—C20—H20B	108.8
O2—C8—N1	125.2 (2)	O6—C21—N2	124.6 (2)
O2—C8—C7	127.3 (2)	O6—C21—C20	127.9 (2)
N1—C8—C7	107.4 (2)	N2—C21—C20	107.4 (2)
N1—C9—C10	111.02 (17)	N2—C22—C23	110.68 (17)
N1—C9—H9A	109.4	N2—C22—H22A	109.5
C10—C9—H9A	109.4	C23—C22—H22A	109.5
N1—C9—H9B	109.4	N2—C22—H22B	109.5
C10—C9—H9B	109.4	C23—C22—H22B	109.5
H9A—C9—H9B	108.0	H22A—C22—H22B	108.1
O1—C10—C3	105.16 (16)	O5—C23—C16	105.36 (16)
O1—C10—C9	109.68 (18)	O5—C23—C22	109.60 (18)
C3—C10—C9	112.49 (17)	C16—C23—C22	112.57 (17)
O1—C10—H10	109.8	O5—C23—H23	109.7
C3—C10—H10	109.8	C16—C23—H23	109.7
C9—C10—H10	109.8	C22—C23—H23	109.7
O4—C11—O3	105.84 (17)	O7—C24—O8	105.71 (15)
O4—C11—C12	109.77 (19)	O7—C24—C25	112.06 (18)
O3—C11—C12	107.39 (19)	O8—C24—C25	109.09 (18)
O4—C11—C13	109.04 (19)	O7—C24—C26	106.94 (18)
O3—C11—C13	111.08 (19)	O8—C24—C26	110.33 (19)
C12—C11—C13	113.4 (2)	C25—C24—C26	112.5 (2)
C11—C12—H12A	109.5	C24—C25—H25A	109.5
C11—C12—H12B	109.5	C24—C25—H25B	109.5
H12A—C12—H12B	109.5	H25A—C25—H25B	109.5
C11—C12—H12C	109.5	C24—C25—H25C	109.5
H12A—C12—H12C	109.5	H25A—C25—H25C	109.5
H12B—C12—H12C	109.5	H25B—C25—H25C	109.5
C11—C13—H13A	109.5	C24—C26—H26A	109.5
C11—C13—H13B	109.5	C24—C26—H26B	109.5
H13A—C13—H13B	109.5	H26A—C26—H26B	109.5
C11—C13—H13C	109.5	C24—C26—H26C	109.5
H13A—C13—H13C	109.5	H26A—C26—H26C	109.5
H13B—C13—H13C	109.5	H26B—C26—H26C	109.5
C10—O1—C1—C2	28.0 (2)	C23—O5—C14—C15	27.7 (2)
C11—O3—C2—C1	−87.4 (2)	C24—O7—C15—C14	−87.3 (2)
C11—O3—C2—C3	26.2 (2)	C24—O7—C15—C16	26.2 (2)
O1—C1—C2—O3	106.57 (19)	O5—C14—C15—O7	107.01 (19)
O1—C1—C2—C3	−7.0 (2)	O5—C14—C15—C16	−6.4 (2)
C11—O4—C3—C4	−115.45 (18)	C24—O8—C16—C17	−114.75 (18)
C11—O4—C3—C10	119.34 (19)	C24—O8—C16—C23	120.00 (17)
C11—O4—C3—C2	9.8 (2)	C24—O8—C16—C15	10.9 (2)
O3—C2—C3—O4	−21.56 (19)	O7—C15—C16—O8	−22.2 (2)
C1—C2—C3—O4	99.46 (18)	C14—C15—C16—O8	98.36 (18)
O3—C2—C3—C4	96.71 (19)	O7—C15—C16—C17	96.3 (2)
C1—C2—C3—C4	−142.27 (18)	C14—C15—C16—C17	−143.09 (18)
O3—C2—C3—C10	−135.54 (16)	O7—C15—C16—C23	−135.84 (17)
C1—C2—C3—C10	−14.5 (2)	C14—C15—C16—C23	−15.3 (2)
O4—C3—C4—C5	−166.15 (17)	O8—C16—C17—C18	−166.48 (16)
C10—C3—C4—C5	−44.2 (2)	C23—C16—C17—C18	−44.8 (2)
C2—C3—C4—C5	78.0 (2)	C15—C16—C17—C18	77.2 (2)
C8—N1—C5—C4	134.9 (2)	C21—N2—C18—C17	140.6 (2)
C9—N1—C5—C4	−56.4 (2)	C22—N2—C18—C17	−57.2 (2)
C8—N1—C5—C6	13.4 (3)	C21—N2—C18—C19	18.6 (3)
C9—N1—C5—C6	−177.93 (19)	C22—N2—C18—C19	−179.3 (2)
C3—C4—C5—N1	47.9 (2)	C16—C17—C18—N2	48.7 (2)
C3—C4—C5—C6	162.08 (19)	C16—C17—C18—C19	162.9 (2)
N1—C5—C6—C7	−19.7 (3)	N2—C18—C19—C20	−23.6 (3)
C4—C5—C6—C7	−137.8 (2)	C17—C18—C19—C20	−141.5 (2)
C5—C6—C7—C8	19.6 (3)	C18—C19—C20—C21	21.4 (3)
C9—N1—C8—O2	9.6 (4)	C22—N2—C21—O6	13.0 (4)
C5—N1—C8—O2	177.3 (2)	C18—N2—C21—O6	173.8 (2)
C9—N1—C8—C7	−168.8 (2)	C22—N2—C21—C20	−166.0 (2)
C5—N1—C8—C7	−1.1 (3)	C18—N2—C21—C20	−5.2 (3)
C6—C7—C8—O2	169.6 (3)	C19—C20—C21—O6	170.3 (3)
C6—C7—C8—N1	−12.1 (3)	C19—C20—C21—N2	−10.8 (3)
C8—N1—C9—C10	−136.6 (2)	C21—N2—C22—C23	−143.0 (2)
C5—N1—C9—C10	56.0 (3)	C18—N2—C22—C23	56.8 (2)
C1—O1—C10—C3	−37.6 (2)	C14—O5—C23—C16	−37.9 (2)
C1—O1—C10—C9	83.6 (2)	C14—O5—C23—C22	83.5 (2)
O4—C3—C10—O1	−77.48 (19)	O8—C16—C23—O5	−76.89 (19)
C4—C3—C10—O1	161.54 (16)	C17—C16—C23—O5	162.28 (16)
C2—C3—C10—O1	31.8 (2)	C15—C16—C23—O5	32.48 (19)
O4—C3—C10—C9	163.20 (17)	O8—C16—C23—C22	163.71 (17)
C4—C3—C10—C9	42.2 (2)	C17—C16—C23—C22	42.9 (2)
C2—C3—C10—C9	−87.5 (2)	C15—C16—C23—C22	−86.91 (19)
N1—C9—C10—O1	−162.63 (17)	N2—C22—C23—O5	−163.21 (17)
N1—C9—C10—C3	−46.0 (2)	N2—C22—C23—C16	−46.3 (2)
C3—O4—C11—O3	5.6 (2)	C15—O7—C24—O8	−19.7 (2)
C3—O4—C11—C12	121.2 (2)	C15—O7—C24—C25	99.0 (2)
C3—O4—C11—C13	−114.0 (2)	C15—O7—C24—C26	−137.31 (19)
C2—O3—C11—O4	−20.5 (2)	C16—O8—C24—O7	4.4 (2)
C2—O3—C11—C12	−137.70 (18)	C16—O8—C24—C25	−116.24 (19)
C2—O3—C11—C13	97.7 (2)	C16—O8—C24—C26	119.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O6^i	0.99	2.53	3.358 (3)	141
C1—H1B···O7^ii	0.99	2.47	3.359 (3)	150
C6—H6B···O2^i	0.99	2.58	3.476 (4)	150
C9—H9B···O2	0.99	2.55	2.904 (3)	101
C14—H14A···O2	0.99	2.50	3.324 (3)	141
C14—H14B···O3^iii	0.99	2.46	3.383 (3)	156
C22—H22A···O2	0.99	2.58	3.527 (3)	160
C22—H22B···O6	0.99	2.56	2.899 (3)	100
C26—H26B···O4^iv	0.98	2.54	3.498 (3)	166

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