(1S,2R,8R)-11-Amino-2,2-di­chloro-3,7,7,10-tetra­methyl­tri­cyclo­[6.4.0.0^1,3]dodec-10-en-9-one

The title compound, C₁₆H₂₃Cl₂NO, crystallizes in the monoclinic space group P2₁ with two independent mol­ecules (A and B) in the asymmetric unit. They have essentially the same conformation. Each mol­ecule is built up from fused six- and seven-membered rings and an additional three-membered ring. The six-membered ring has an envelope conformation, with the C atom belonging to the three-membered ring forming the flap, while the seven-membered ring displays a boat conformation. In the crystal, mol­ecules are linked into chains propagating along the a-axis direction by N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.038
• wR factor = 0.094
• Data-to-parameter ratio = 22.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00433 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N1     --  H1A    ...     Please Check
PLAT420_ALERT_2_C D-H Without Acceptor       N2     --  H2A    ...     Please Check

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT791_ALERT_4_G The Model has Chirality at C1      (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C3      (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C8      (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C17     (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C19     (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C24     (Chiral SPGR)          R Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           3 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          5 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  10 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

(1S,2R,8R)-11-Amino-2,2-dichloro-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3]dodec-10-en-9-one

Crystal data

C16H23Cl2NO	F(000) = 672
Mr = 316.25	Dx = 1.296 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 6.9962 (13) Å	Cell parameters from 6632 reflections
b = 18.654 (4) Å	θ = 1.6–26.4°
c = 12.426 (3) Å	µ = 0.40 mm^−1
β = 91.273 (5)°	T = 296 K
V = 1621.4 (5) Å^3	Prismatic, colourless
Z = 4	0.24 × 0.2 × 0.15 mm

Data collection

Bruker X8 APEX diffractometer	6511 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.053
φ and ω scans	θmax = 28.7°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→8
Tmin = 0.629, Tmax = 0.747	k = −25→25
58110 measured reflections	l = −16→16
8375 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.038	w = 1/[σ^2(Fo^2) + (0.0442P)^2 + 0.1774P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.094	(Δ/σ)max = 0.001
S = 1.02	Δρmax = 0.26 e Å^−3
8375 reflections	Δρmin = −0.18 e Å^−3
369 parameters	Absolute structure: Flack x determined using 2672 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.010 (18)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.3670 (4)	0.62609 (15)	0.5109 (2)	0.0342 (6)
C2	0.3868 (5)	0.69648 (17)	0.5700 (2)	0.0469 (7)
C3	0.3294 (5)	0.63016 (17)	0.6324 (2)	0.0452 (7)
C4	0.4790 (6)	0.59418 (18)	0.7054 (2)	0.0540 (8)
H4A	0.4594	0.6086	0.7793	0.065*
H4B	0.6054	0.6099	0.6852	0.065*
C5	0.4675 (6)	0.51212 (19)	0.6972 (3)	0.0610 (10)
H5A	0.5883	0.4923	0.7228	0.073*
H5B	0.3694	0.4955	0.7452	0.073*
C6	0.4241 (5)	0.48237 (17)	0.5853 (2)	0.0497 (8)
H6A	0.2932	0.4951	0.5664	0.060*
H6B	0.4292	0.4305	0.5902	0.060*
C7	0.5494 (4)	0.50495 (15)	0.4912 (2)	0.0419 (7)
C8	0.5481 (4)	0.58915 (14)	0.4760 (2)	0.0336 (6)
H8	0.6508	0.6076	0.5232	0.040*
C9	0.5984 (4)	0.61206 (16)	0.3623 (2)	0.0375 (6)
C10	0.4512 (4)	0.63564 (15)	0.2889 (2)	0.0345 (6)
C11	0.2637 (4)	0.63392 (14)	0.3179 (2)	0.0321 (5)
C12	0.2033 (4)	0.61729 (17)	0.4302 (2)	0.0374 (6)
H12A	0.1563	0.5684	0.4330	0.045*
H12B	0.0996	0.6490	0.4493	0.045*
C13	0.1274 (6)	0.6244 (2)	0.6731 (3)	0.0649 (10)
H13A	0.1181	0.6502	0.7396	0.097*
H13B	0.0963	0.5749	0.6846	0.097*
H13C	0.0397	0.6445	0.6208	0.097*
C14	0.7561 (6)	0.4808 (2)	0.5124 (4)	0.0719 (11)
H14A	0.7604	0.4294	0.5177	0.108*
H14B	0.8032	0.5014	0.5786	0.108*
H14C	0.8343	0.4962	0.4543	0.108*
C15	0.4721 (6)	0.46588 (19)	0.3904 (3)	0.0609 (9)
H15A	0.5429	0.4807	0.3290	0.091*
H15B	0.3395	0.4775	0.3791	0.091*
H15C	0.4857	0.4151	0.4002	0.091*
C16	0.5071 (5)	0.65700 (18)	0.1765 (2)	0.0463 (7)
H16A	0.4695	0.6200	0.1267	0.069*
H16B	0.6431	0.6636	0.1746	0.069*
H16C	0.4442	0.7010	0.1569	0.069*
C17	−0.0333 (4)	0.41311 (14)	−0.0173 (2)	0.0318 (6)
C18	−0.0172 (4)	0.49436 (15)	−0.0174 (2)	0.0393 (6)
C19	−0.0796 (4)	0.45709 (16)	0.0835 (2)	0.0415 (7)
C20	0.0609 (6)	0.45095 (18)	0.1779 (2)	0.0522 (8)
H20A	0.0326	0.4878	0.2303	0.063*
H20B	0.1892	0.4593	0.1528	0.063*
C21	0.0535 (7)	0.3772 (2)	0.2327 (3)	0.0652 (10)
H21A	0.1744	0.3691	0.2705	0.078*
H21B	−0.0455	0.3783	0.2861	0.078*
C22	0.0149 (6)	0.31356 (18)	0.1570 (3)	0.0562 (9)
H22A	−0.1151	0.3182	0.1292	0.067*
H22B	0.0194	0.2703	0.2004	0.067*
C23	0.1448 (5)	0.30144 (16)	0.0602 (2)	0.0447 (7)
C24	0.1500 (4)	0.36961 (14)	−0.0151 (2)	0.0324 (6)
H24	0.2501	0.4011	0.0148	0.039*
C25	0.2082 (4)	0.35152 (15)	−0.1298 (2)	0.0348 (6)
C26	0.0656 (4)	0.34250 (15)	−0.2124 (2)	0.0342 (6)
C27	−0.1239 (4)	0.35081 (14)	−0.1896 (2)	0.0306 (5)
C28	−0.1911 (4)	0.37905 (15)	−0.0838 (2)	0.0337 (6)
H28A	−0.2459	0.3400	−0.0433	0.040*
H28B	−0.2910	0.4142	−0.0971	0.040*
C29	−0.2869 (5)	0.4639 (2)	0.1167 (3)	0.0613 (9)
H29A	−0.3029	0.5074	0.1567	0.092*
H29B	−0.3201	0.4237	0.1608	0.092*
H29C	−0.3686	0.4648	0.0536	0.092*
C30	0.3499 (6)	0.2850 (3)	0.0979 (4)	0.0789 (13)
H30A	0.3518	0.2413	0.1386	0.118*
H30B	0.3970	0.3236	0.1423	0.118*
H30C	0.4296	0.2799	0.0365	0.118*
C31	0.0658 (6)	0.23478 (18)	−0.0001 (3)	0.0628 (10)
H31A	0.0671	0.1944	0.0478	0.094*
H31B	0.1441	0.2247	−0.0607	0.094*
H31C	−0.0629	0.2440	−0.0247	0.094*
C32	0.1267 (5)	0.31821 (19)	−0.3219 (2)	0.0491 (8)
H32A	0.0893	0.2692	−0.3330	0.074*
H32B	0.2631	0.3222	−0.3266	0.074*
H32C	0.0668	0.3478	−0.3762	0.074*
N1	0.1202 (4)	0.64687 (15)	0.24803 (19)	0.0442 (6)
H1A	0.1440	0.6567	0.1821	0.053*
H1B	0.0039	0.6453	0.2690	0.053*
N2	−0.2662 (3)	0.33465 (14)	−0.25976 (19)	0.0419 (6)
H2A	−0.2403	0.3182	−0.3224	0.050*
H2B	−0.3832	0.3407	−0.2420	0.050*
O1	0.7681 (3)	0.60721 (15)	0.3360 (2)	0.0583 (6)
O2	0.3815 (3)	0.34305 (14)	−0.14593 (19)	0.0532 (6)
Cl1	0.20775 (13)	0.53695 (4)	−0.02330 (7)	0.0559 (2)
Cl2	−0.18423 (14)	0.54562 (5)	−0.09233 (7)	0.0629 (2)
Cl3	0.61389 (17)	0.73707 (5)	0.58908 (8)	0.0714 (3)
Cl4	0.21570 (18)	0.76477 (5)	0.54750 (8)	0.0734 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0363 (15)	0.0378 (14)	0.0286 (12)	−0.0006 (11)	0.0015 (10)	0.0034 (10)
C2	0.064 (2)	0.0387 (16)	0.0383 (16)	0.0063 (14)	−0.0031 (14)	0.0014 (12)
C3	0.063 (2)	0.0415 (16)	0.0313 (14)	0.0066 (14)	0.0002 (13)	−0.0024 (12)
C4	0.081 (2)	0.0484 (18)	0.0322 (15)	0.0021 (17)	−0.0087 (15)	0.0000 (13)
C5	0.095 (3)	0.0488 (19)	0.0386 (17)	0.0041 (18)	−0.0074 (17)	0.0117 (14)
C6	0.066 (2)	0.0350 (15)	0.0483 (17)	−0.0053 (14)	0.0016 (15)	0.0064 (13)
C7	0.0438 (18)	0.0338 (14)	0.0480 (17)	−0.0002 (12)	−0.0011 (13)	0.0021 (12)
C8	0.0306 (15)	0.0324 (13)	0.0375 (14)	−0.0032 (11)	−0.0042 (11)	0.0023 (11)
C9	0.0280 (15)	0.0396 (15)	0.0450 (15)	−0.0056 (12)	0.0046 (12)	0.0011 (12)
C10	0.0317 (15)	0.0381 (14)	0.0339 (13)	−0.0042 (11)	0.0042 (11)	0.0034 (11)
C11	0.0319 (15)	0.0307 (13)	0.0337 (13)	−0.0025 (10)	0.0006 (11)	0.0022 (10)
C12	0.0305 (14)	0.0486 (16)	0.0334 (13)	0.0018 (12)	0.0043 (11)	0.0030 (11)
C13	0.082 (3)	0.072 (2)	0.0418 (18)	0.012 (2)	0.0242 (17)	0.0027 (17)
C14	0.055 (2)	0.050 (2)	0.111 (3)	0.0146 (17)	0.002 (2)	0.015 (2)
C15	0.086 (3)	0.0411 (18)	0.0554 (19)	−0.0044 (18)	0.0070 (18)	−0.0075 (15)
C16	0.0466 (19)	0.0526 (18)	0.0400 (16)	−0.0035 (14)	0.0112 (13)	0.0070 (13)
C17	0.0338 (15)	0.0302 (13)	0.0314 (13)	−0.0025 (11)	0.0028 (11)	−0.0043 (10)
C18	0.0471 (17)	0.0319 (14)	0.0385 (15)	−0.0022 (12)	−0.0060 (12)	−0.0032 (11)
C19	0.0534 (19)	0.0340 (14)	0.0374 (14)	−0.0024 (13)	0.0043 (12)	−0.0089 (12)
C20	0.079 (2)	0.0444 (17)	0.0331 (14)	−0.0099 (16)	−0.0053 (14)	−0.0059 (13)
C21	0.105 (3)	0.055 (2)	0.0358 (17)	−0.013 (2)	−0.0030 (18)	0.0026 (15)
C22	0.084 (3)	0.0430 (18)	0.0419 (17)	−0.0079 (17)	0.0071 (17)	0.0063 (13)
C23	0.0509 (19)	0.0364 (15)	0.0468 (17)	−0.0008 (13)	0.0002 (14)	0.0063 (13)
C24	0.0300 (14)	0.0326 (13)	0.0346 (13)	−0.0033 (11)	−0.0029 (11)	−0.0023 (10)
C25	0.0276 (15)	0.0336 (13)	0.0432 (15)	−0.0025 (11)	0.0049 (11)	−0.0008 (11)
C26	0.0316 (15)	0.0363 (14)	0.0351 (13)	−0.0040 (11)	0.0053 (11)	−0.0061 (11)
C27	0.0307 (14)	0.0290 (12)	0.0323 (12)	−0.0040 (10)	0.0011 (10)	−0.0028 (10)
C28	0.0252 (13)	0.0375 (14)	0.0386 (14)	−0.0015 (11)	0.0040 (11)	−0.0087 (11)
C29	0.067 (2)	0.059 (2)	0.059 (2)	0.0056 (19)	0.0206 (17)	−0.0196 (18)
C30	0.071 (3)	0.081 (3)	0.084 (3)	0.017 (2)	−0.016 (2)	0.030 (2)
C31	0.091 (3)	0.0307 (15)	0.067 (2)	0.0023 (17)	0.012 (2)	−0.0013 (15)
C32	0.0436 (18)	0.060 (2)	0.0441 (17)	−0.0082 (15)	0.0144 (14)	−0.0128 (15)
N1	0.0338 (14)	0.0620 (17)	0.0367 (13)	−0.0003 (12)	−0.0009 (10)	0.0118 (12)
N2	0.0331 (13)	0.0545 (15)	0.0379 (12)	−0.0010 (11)	−0.0001 (10)	−0.0134 (11)
O1	0.0245 (11)	0.0809 (18)	0.0700 (15)	−0.0016 (11)	0.0104 (10)	0.0140 (13)
O2	0.0244 (11)	0.0735 (16)	0.0620 (14)	0.0005 (10)	0.0066 (9)	−0.0087 (12)
Cl1	0.0660 (5)	0.0450 (4)	0.0565 (4)	−0.0231 (4)	−0.0068 (4)	0.0036 (4)
Cl2	0.0772 (6)	0.0421 (4)	0.0684 (5)	0.0142 (4)	−0.0204 (4)	−0.0017 (4)
Cl3	0.0953 (8)	0.0444 (4)	0.0734 (6)	−0.0183 (5)	−0.0224 (5)	−0.0053 (4)
Cl4	0.1074 (8)	0.0535 (5)	0.0593 (5)	0.0355 (5)	0.0064 (5)	0.0030 (4)

Geometric parameters (Å, º)

C1—C2	1.509 (4)	C17—C18	1.520 (4)
C1—C8	1.514 (4)	C17—C19	1.538 (4)
C1—C12	1.515 (4)	C18—C19	1.506 (4)
C1—C3	1.540 (4)	C18—Cl2	1.760 (3)
C2—C3	1.519 (4)	C18—Cl1	1.766 (3)
C2—Cl4	1.766 (3)	C19—C20	1.518 (4)
C2—Cl3	1.771 (4)	C19—C29	1.522 (5)
C3—C13	1.515 (5)	C20—C21	1.536 (5)
C3—C4	1.525 (4)	C20—H20A	0.9700
C4—C5	1.536 (5)	C20—H20B	0.9700
C4—H4A	0.9700	C21—C22	1.534 (5)
C4—H4B	0.9700	C21—H21A	0.9700
C5—C6	1.521 (4)	C21—H21B	0.9700
C5—H5A	0.9700	C22—C23	1.541 (5)
C5—H5B	0.9700	C22—H22A	0.9700
C6—C7	1.536 (4)	C22—H22B	0.9700
C6—H6A	0.9700	C23—C30	1.530 (5)
C6—H6B	0.9700	C23—C31	1.547 (5)
C7—C14	1.533 (5)	C23—C24	1.580 (4)
C7—C15	1.537 (5)	C24—C25	1.529 (4)
C7—C8	1.582 (4)	C24—H24	0.9800
C8—C9	1.524 (4)	C25—O2	1.243 (3)
C8—H8	0.9800	C25—C26	1.425 (4)
C9—O1	1.241 (3)	C26—C27	1.371 (4)
C9—C10	1.430 (4)	C26—C32	1.506 (4)
C10—C11	1.369 (4)	C27—N2	1.343 (3)
C10—C16	1.512 (4)	C27—C28	1.501 (3)
C11—N1	1.335 (3)	C28—H28A	0.9700
C11—C12	1.499 (4)	C28—H28B	0.9700
C12—H12A	0.9700	C29—H29A	0.9600
C12—H12B	0.9700	C29—H29B	0.9600
C13—H13A	0.9600	C29—H29C	0.9600
C13—H13B	0.9600	C30—H30A	0.9600
C13—H13C	0.9600	C30—H30B	0.9600
C14—H14A	0.9600	C30—H30C	0.9600
C14—H14B	0.9600	C31—H31A	0.9600
C14—H14C	0.9600	C31—H31B	0.9600
C15—H15A	0.9600	C31—H31C	0.9600
C15—H15B	0.9600	C32—H32A	0.9600
C15—H15C	0.9600	C32—H32B	0.9600
C16—H16A	0.9600	C32—H32C	0.9600
C16—H16B	0.9600	N1—H1A	0.8600
C16—H16C	0.9600	N1—H1B	0.8600
C17—C28	1.505 (4)	N2—H2A	0.8600
C17—C24	1.517 (4)	N2—H2B	0.8600
C2—C1—C8	117.9 (2)	C28—C17—C19	120.5 (2)
C2—C1—C12	118.4 (3)	C24—C17—C19	117.7 (2)
C8—C1—C12	112.7 (2)	C18—C17—C19	59.03 (18)
C2—C1—C3	59.76 (19)	C19—C18—C17	61.08 (18)
C8—C1—C3	117.8 (2)	C19—C18—Cl2	119.3 (2)
C12—C1—C3	120.8 (2)	C17—C18—Cl2	119.6 (2)
C1—C2—C3	61.13 (19)	C19—C18—Cl1	121.2 (2)
C1—C2—Cl4	119.8 (2)	C17—C18—Cl1	121.0 (2)
C3—C2—Cl4	118.8 (2)	Cl2—C18—Cl1	108.38 (16)
C1—C2—Cl3	120.6 (2)	C18—C19—C20	118.9 (3)
C3—C2—Cl3	121.7 (2)	C18—C19—C29	118.9 (3)
Cl4—C2—Cl3	108.40 (18)	C20—C19—C29	113.6 (3)
C13—C3—C2	119.1 (3)	C18—C19—C17	59.90 (17)
C13—C3—C4	113.8 (3)	C20—C19—C17	116.4 (3)
C2—C3—C4	118.4 (3)	C29—C19—C17	119.0 (3)
C13—C3—C1	120.3 (3)	C19—C20—C21	112.5 (3)
C2—C3—C1	59.10 (19)	C19—C20—H20A	109.1
C4—C3—C1	115.5 (3)	C21—C20—H20A	109.1
C3—C4—C5	111.4 (3)	C19—C20—H20B	109.1
C3—C4—H4A	109.3	C21—C20—H20B	109.1
C5—C4—H4A	109.3	H20A—C20—H20B	107.8
C3—C4—H4B	109.3	C22—C21—C20	115.4 (3)
C5—C4—H4B	109.3	C22—C21—H21A	108.4
H4A—C4—H4B	108.0	C20—C21—H21A	108.4
C6—C5—C4	115.7 (3)	C22—C21—H21B	108.4
C6—C5—H5A	108.4	C20—C21—H21B	108.4
C4—C5—H5A	108.4	H21A—C21—H21B	107.5
C6—C5—H5B	108.4	C21—C22—C23	119.5 (3)
C4—C5—H5B	108.4	C21—C22—H22A	107.4
H5A—C5—H5B	107.4	C23—C22—H22A	107.4
C5—C6—C7	119.3 (3)	C21—C22—H22B	107.4
C5—C6—H6A	107.5	C23—C22—H22B	107.4
C7—C6—H6A	107.5	H22A—C22—H22B	107.0
C5—C6—H6B	107.5	C30—C23—C22	110.8 (3)
C7—C6—H6B	107.5	C30—C23—C31	108.1 (3)
H6A—C6—H6B	107.0	C22—C23—C31	106.6 (3)
C14—C7—C6	109.9 (3)	C30—C23—C24	108.0 (3)
C14—C7—C15	108.3 (3)	C22—C23—C24	111.5 (3)
C6—C7—C15	107.1 (3)	C31—C23—C24	111.9 (3)
C14—C7—C8	108.4 (3)	C17—C24—C25	110.1 (2)
C6—C7—C8	111.2 (2)	C17—C24—C23	114.2 (2)
C15—C7—C8	111.9 (3)	C25—C24—C23	112.6 (2)
C1—C8—C9	110.5 (2)	C17—C24—H24	106.4
C1—C8—C7	114.8 (2)	C25—C24—H24	106.4
C9—C8—C7	112.9 (2)	C23—C24—H24	106.4
C1—C8—H8	106.0	O2—C25—C26	122.6 (2)
C9—C8—H8	106.0	O2—C25—C24	117.3 (2)
C7—C8—H8	106.0	C26—C25—C24	120.0 (2)
O1—C9—C10	122.3 (3)	C27—C26—C25	120.2 (2)
O1—C9—C8	117.7 (3)	C27—C26—C32	121.1 (2)
C10—C9—C8	120.0 (2)	C25—C26—C32	118.5 (2)
C11—C10—C9	120.4 (2)	N2—C27—C26	123.2 (2)
C11—C10—C16	121.2 (3)	N2—C27—C28	113.9 (2)
C9—C10—C16	118.2 (2)	C26—C27—C28	122.9 (2)
N1—C11—C10	122.4 (2)	C27—C28—C17	112.9 (2)
N1—C11—C12	114.8 (2)	C27—C28—H28A	109.0
C10—C11—C12	122.8 (2)	C17—C28—H28A	109.0
C11—C12—C1	111.7 (2)	C27—C28—H28B	109.0
C11—C12—H12A	109.3	C17—C28—H28B	109.0
C1—C12—H12A	109.3	H28A—C28—H28B	107.8
C11—C12—H12B	109.3	C19—C29—H29A	109.5
C1—C12—H12B	109.3	C19—C29—H29B	109.5
H12A—C12—H12B	107.9	H29A—C29—H29B	109.5
C3—C13—H13A	109.5	C19—C29—H29C	109.5
C3—C13—H13B	109.5	H29A—C29—H29C	109.5
H13A—C13—H13B	109.5	H29B—C29—H29C	109.5
C3—C13—H13C	109.5	C23—C30—H30A	109.5
H13A—C13—H13C	109.5	C23—C30—H30B	109.5
H13B—C13—H13C	109.5	H30A—C30—H30B	109.5
C7—C14—H14A	109.5	C23—C30—H30C	109.5
C7—C14—H14B	109.5	H30A—C30—H30C	109.5
H14A—C14—H14B	109.5	H30B—C30—H30C	109.5
C7—C14—H14C	109.5	C23—C31—H31A	109.5
H14A—C14—H14C	109.5	C23—C31—H31B	109.5
H14B—C14—H14C	109.5	H31A—C31—H31B	109.5
C7—C15—H15A	109.5	C23—C31—H31C	109.5
C7—C15—H15B	109.5	H31A—C31—H31C	109.5
H15A—C15—H15B	109.5	H31B—C31—H31C	109.5
C7—C15—H15C	109.5	C26—C32—H32A	109.5
H15A—C15—H15C	109.5	C26—C32—H32B	109.5
H15B—C15—H15C	109.5	H32A—C32—H32B	109.5
C10—C16—H16A	109.5	C26—C32—H32C	109.5
C10—C16—H16B	109.5	H32A—C32—H32C	109.5
H16A—C16—H16B	109.5	H32B—C32—H32C	109.5
C10—C16—H16C	109.5	C11—N1—H1A	120.0
H16A—C16—H16C	109.5	C11—N1—H1B	120.0
H16B—C16—H16C	109.5	H1A—N1—H1B	120.0
C28—C17—C24	113.2 (2)	C27—N2—H2A	120.0
C28—C17—C18	118.3 (2)	C27—N2—H2B	120.0
C24—C17—C18	118.1 (2)	H2A—N2—H2B	120.0

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1^i	0.86	2.00	2.816 (3)	159
N2—H2B···O2^i	0.86	2.06	2.873 (3)	159

Symmetry code: (i) x−1, y, z.