4,11-Bis(4-methoxy­phenyl)-3,10-bis(2,6-di­chloro­phenyl)-1,8-dioxa-2,9-di­aza­di­spiro­[4.1.4.3]­tetra­deca-2,9-dien-6-one-chloro­form-methanol (2/2/1)

The title compound, C₃₆H₂₈Cl₄N₂O₅·CHCl₃·0.5CH₄O, was synthesized by the intermolecular [3+2]-cyclo­addition of 2,6-di­chloro­benzo­nitrile oxide and 2,6-bis(4-methoxy­benzyl­idene)­cyclo­hexanone. There are three rings linked by two spiro-C atoms. The cyclo­hexane ring has a chair conformation and the two five-membered isoxazoline rings have envelope conformations.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in solvent or counterion
• R factor = 0.068
• wR factor = 0.232
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.99
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.07 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.66 Ratio
PLAT244_ALERT_4_C Low Solvent  U(eq) as Compared to Neighbors ....        C37
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      17.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

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

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

---

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

4,11-Bis(4-methoxyphenyl)-3,10-bis(2,6-dichlorophenyl)-1,8-dioxa-2,9- diazadispiro[4.1.4.3]tetradeca-2,9-dien-6-one–chloroform–water (2/2/1)

Crystal data

C36H28Cl4N2O5·CHCl3·0.5CH4O	Z = 2
Mr = 845.79	F(000) = 866
Triclinic, P1	Dx = 1.443 Mg m^−3
Hall symbol: -P 1	Melting point = 521–522 K
a = 11.293 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.955 (4) Å	Cell parameters from 956 reflections
c = 15.027 (4) Å	θ = 3.5–23.5°
α = 114.946 (4)°	µ = 0.56 mm^−1
β = 96.953 (5)°	T = 293 K
γ = 96.393 (5)°	Block, colorless
V = 1946.2 (10) Å^3	0.38 × 0.36 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer	6824 independent reflections
Radiation source: fine-focus sealed tube	4415 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −13→13
Tmin = 0.732, Tmax = 0.856	k = −13→15
10073 measured reflections	l = −17→10

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.068	w = 1/[σ^2(Fo^2) + (0.084P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.232	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.64 e Å^−3
6824 reflections	Δρmin = −0.77 e Å^−3
480 parameters

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)
Cl1	−0.22458 (14)	0.49499 (12)	0.11480 (12)	0.0782 (4)
Cl2	−0.36036 (14)	0.88541 (14)	0.11735 (12)	0.0831 (5)
Cl3	0.31732 (16)	1.34688 (13)	0.46191 (11)	0.0914 (5)
Cl4	−0.09293 (14)	1.02722 (17)	0.35206 (14)	0.0962 (5)
N1	−0.0862 (3)	0.7395 (3)	0.1614 (2)	0.0439 (8)
N2	0.1180 (3)	1.1893 (3)	0.2564 (3)	0.0496 (9)
O1	−0.0800 (3)	0.9843 (2)	0.0931 (2)	0.0514 (7)
O2	0.0202 (2)	0.7709 (2)	0.1308 (2)	0.0429 (7)
O3	−0.2306 (4)	0.3279 (3)	−0.3501 (2)	0.0710 (10)
O4	0.1361 (3)	1.1193 (2)	0.1592 (2)	0.0476 (7)
O5	0.6309 (3)	0.9759 (4)	0.3962 (3)	0.0730 (10)
C1	0.0021 (3)	0.9346 (3)	0.0962 (3)	0.0350 (8)
C2	−0.0150 (3)	0.8014 (3)	0.0488 (3)	0.0369 (8)
C3	0.0753 (4)	0.7636 (4)	−0.0215 (3)	0.0490 (10)
H3A	0.0681	0.6801	−0.0505	0.059*
H3B	0.0570	0.7852	−0.0754	0.059*
C4	0.2040 (4)	0.8205 (4)	0.0351 (3)	0.0491 (10)
H4A	0.2218	0.7983	0.0887	0.059*
H4B	0.2605	0.7928	−0.0098	0.059*
C5	0.2221 (4)	0.9503 (4)	0.0783 (3)	0.0438 (9)
H5A	0.2132	0.9726	0.0242	0.053*
H5B	0.3041	0.9826	0.1162	0.053*
C6	0.1326 (3)	1.0016 (3)	0.1464 (3)	0.0382 (9)
C7	−0.1496 (3)	0.7436 (3)	0.0086 (3)	0.0369 (8)
H7	−0.1964	0.7991	−0.0001	0.044*
C8	−0.1783 (3)	0.7262 (3)	0.0977 (3)	0.0394 (9)
C9	−0.3001 (4)	0.6861 (4)	0.1111 (3)	0.0465 (10)
C10	−0.3302 (4)	0.5837 (4)	0.1190 (3)	0.0582 (12)
C11	−0.4454 (5)	0.5472 (6)	0.1301 (4)	0.0783 (17)
H11	−0.4626	0.4784	0.1354	0.094*
C12	−0.5329 (5)	0.6118 (7)	0.1331 (4)	0.088 (2)
H12	−0.6105	0.5861	0.1390	0.105*
C13	−0.5072 (5)	0.7153 (7)	0.1276 (4)	0.0804 (18)
H13	−0.5670	0.7601	0.1308	0.096*
C14	−0.3919 (4)	0.7523 (5)	0.1172 (3)	0.0585 (12)
C15	−0.1772 (3)	0.6322 (3)	−0.0865 (3)	0.0369 (8)
C16	−0.2437 (4)	0.6257 (4)	−0.1719 (3)	0.0469 (10)
H16	−0.2761	0.6895	−0.1697	0.056*
C17	−0.2639 (4)	0.5259 (4)	−0.2619 (3)	0.0545 (11)
H17	−0.3083	0.5237	−0.3192	0.065*
C18	−0.2179 (4)	0.4305 (4)	−0.2656 (3)	0.0484 (10)
C19	−0.1537 (4)	0.4339 (4)	−0.1808 (3)	0.0477 (10)
H19	−0.1235	0.3691	−0.1830	0.057*
C20	−0.1337 (4)	0.5337 (4)	−0.0917 (3)	0.0452 (10)
H20	−0.0906	0.5349	−0.0343	0.054*
C21	−0.2875 (8)	0.3205 (6)	−0.4423 (4)	0.107 (2)
H21A	−0.3691	0.3339	−0.4385	0.161*
H21B	−0.2889	0.2449	−0.4945	0.161*
H21C	−0.2432	0.3778	−0.4565	0.161*
C22	0.1580 (3)	1.0144 (3)	0.2553 (3)	0.0373 (8)
H22	0.0980	0.9581	0.2614	0.045*
C23	0.1279 (4)	1.1338 (3)	0.3083 (3)	0.0423 (9)
C24	0.1128 (4)	1.1867 (4)	0.4140 (3)	0.0532 (11)
C25	0.1923 (6)	1.2829 (4)	0.4895 (4)	0.0685 (14)
C26	0.1762 (8)	1.3301 (6)	0.5878 (4)	0.091 (2)
H26	0.2300	1.3943	0.6366	0.110*
C27	0.0801 (9)	1.2805 (8)	0.6114 (5)	0.107 (3)
H27	0.0702	1.3107	0.6776	0.129*
C28	−0.0031 (7)	1.1870 (7)	0.5406 (5)	0.093 (2)
H28	−0.0695	1.1556	0.5580	0.111*
C29	0.0151 (5)	1.1412 (5)	0.4425 (4)	0.0673 (14)
C30	0.2832 (3)	1.0044 (3)	0.2951 (3)	0.0372 (9)
C31	0.2993 (4)	0.9149 (3)	0.3194 (3)	0.0416 (9)
H31	0.2318	0.8623	0.3130	0.050*
C32	0.4139 (4)	0.9014 (4)	0.3534 (3)	0.0494 (10)
H32	0.4228	0.8399	0.3687	0.059*
C33	0.5146 (4)	0.9795 (4)	0.3642 (3)	0.0503 (11)
C34	0.4993 (4)	1.0699 (4)	0.3399 (3)	0.0522 (11)
H34	0.5668	1.1224	0.3464	0.063*
C35	0.3862 (4)	1.0827 (4)	0.3065 (3)	0.0450 (10)
H35	0.3778	1.1443	0.2911	0.054*
C36	0.6530 (5)	0.8812 (5)	0.4150 (4)	0.0759 (16)
H36A	0.6078	0.8777	0.4641	0.114*
H36B	0.7380	0.8907	0.4394	0.114*
H36C	0.6282	0.8109	0.3543	0.114*
C37	0.6634 (10)	0.2806 (7)	0.2190 (6)	0.130 (3)
H37	0.7136	0.3337	0.2019	0.156*
Cl5	0.6127 (4)	0.3611 (2)	0.3255 (2)	0.1736 (12)
Cl6	0.5396 (3)	0.2068 (4)	0.1217 (2)	0.1893 (14)
Cl7	0.7472 (3)	0.1841 (3)	0.2289 (3)	0.1951 (14)
C38	0.9830 (18)	0.4317 (14)	0.3849 (11)	0.171 (10)	0.50
H38A	1.0697	0.4500	0.4052	0.257*	0.50
H38B	0.9518	0.3673	0.3964	0.257*	0.50
H38C	0.9485	0.4975	0.4228	0.257*	0.50
O6	0.9519 (10)	0.4021 (10)	0.2805 (9)	0.120 (4)	0.50
H6	0.9972	0.4250	0.2488	0.144*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0866 (10)	0.0596 (8)	0.1011 (11)	0.0131 (7)	0.0337 (8)	0.0434 (8)
Cl2	0.0794 (10)	0.0859 (10)	0.0982 (11)	0.0481 (8)	0.0356 (8)	0.0409 (9)
Cl3	0.1083 (12)	0.0645 (9)	0.0688 (9)	−0.0088 (8)	0.0066 (8)	0.0073 (7)
Cl4	0.0682 (9)	0.1178 (13)	0.1119 (13)	0.0067 (9)	0.0399 (9)	0.0557 (11)
N1	0.0428 (19)	0.0419 (19)	0.0457 (19)	0.0044 (15)	0.0061 (16)	0.0193 (16)
N2	0.061 (2)	0.045 (2)	0.042 (2)	0.0076 (17)	0.0098 (16)	0.0181 (17)
O1	0.0490 (17)	0.0445 (16)	0.0578 (19)	0.0153 (14)	0.0026 (14)	0.0202 (14)
O2	0.0339 (14)	0.0442 (16)	0.0558 (17)	0.0065 (12)	0.0005 (12)	0.0293 (14)
O3	0.099 (3)	0.0472 (19)	0.0476 (19)	−0.0015 (18)	0.0059 (18)	0.0089 (15)
O4	0.0665 (19)	0.0389 (15)	0.0398 (15)	0.0035 (13)	0.0106 (13)	0.0207 (13)
O5	0.0445 (19)	0.103 (3)	0.089 (3)	0.0165 (18)	0.0050 (17)	0.061 (2)
C1	0.040 (2)	0.040 (2)	0.0284 (18)	0.0113 (17)	0.0082 (15)	0.0170 (17)
C2	0.035 (2)	0.036 (2)	0.039 (2)	0.0071 (16)	0.0035 (16)	0.0164 (17)
C3	0.042 (2)	0.044 (2)	0.052 (3)	0.0105 (18)	0.0139 (19)	0.011 (2)
C4	0.038 (2)	0.058 (3)	0.049 (2)	0.0111 (19)	0.0144 (18)	0.019 (2)
C5	0.039 (2)	0.053 (2)	0.040 (2)	0.0000 (18)	0.0071 (17)	0.0223 (19)
C6	0.043 (2)	0.036 (2)	0.037 (2)	0.0002 (17)	0.0025 (17)	0.0197 (17)
C7	0.0316 (19)	0.037 (2)	0.041 (2)	0.0079 (16)	0.0065 (16)	0.0155 (17)
C8	0.038 (2)	0.039 (2)	0.040 (2)	0.0111 (17)	0.0068 (17)	0.0146 (17)
C9	0.041 (2)	0.055 (3)	0.035 (2)	0.0069 (19)	0.0104 (17)	0.0117 (19)
C10	0.056 (3)	0.066 (3)	0.043 (2)	−0.005 (2)	0.012 (2)	0.018 (2)
C11	0.069 (4)	0.090 (4)	0.065 (3)	−0.012 (3)	0.021 (3)	0.027 (3)
C12	0.053 (3)	0.127 (6)	0.066 (4)	−0.007 (4)	0.022 (3)	0.030 (4)
C13	0.044 (3)	0.131 (6)	0.057 (3)	0.024 (3)	0.017 (2)	0.029 (3)
C14	0.045 (3)	0.079 (3)	0.045 (3)	0.017 (2)	0.014 (2)	0.019 (2)
C15	0.0309 (19)	0.039 (2)	0.041 (2)	0.0033 (16)	0.0062 (16)	0.0179 (17)
C16	0.053 (3)	0.043 (2)	0.047 (2)	0.0054 (19)	0.005 (2)	0.025 (2)
C17	0.065 (3)	0.052 (3)	0.040 (2)	−0.003 (2)	−0.004 (2)	0.021 (2)
C18	0.059 (3)	0.037 (2)	0.041 (2)	−0.0041 (19)	0.006 (2)	0.0130 (19)
C19	0.052 (3)	0.039 (2)	0.052 (3)	0.0089 (19)	0.008 (2)	0.020 (2)
C20	0.045 (2)	0.045 (2)	0.042 (2)	0.0081 (19)	0.0006 (18)	0.019 (2)
C21	0.161 (7)	0.082 (4)	0.045 (3)	0.007 (4)	−0.010 (4)	0.008 (3)
C22	0.039 (2)	0.037 (2)	0.036 (2)	−0.0005 (16)	0.0047 (16)	0.0183 (17)
C23	0.045 (2)	0.044 (2)	0.039 (2)	0.0069 (18)	0.0090 (18)	0.0197 (19)
C24	0.071 (3)	0.052 (3)	0.045 (2)	0.027 (2)	0.019 (2)	0.024 (2)
C25	0.104 (4)	0.058 (3)	0.042 (3)	0.032 (3)	0.013 (3)	0.016 (2)
C26	0.146 (6)	0.081 (4)	0.046 (3)	0.039 (4)	0.022 (4)	0.020 (3)
C27	0.177 (8)	0.117 (6)	0.053 (4)	0.079 (6)	0.049 (5)	0.042 (4)
C28	0.126 (6)	0.110 (5)	0.084 (5)	0.062 (5)	0.067 (4)	0.061 (4)
C29	0.077 (4)	0.078 (4)	0.068 (3)	0.035 (3)	0.033 (3)	0.043 (3)
C30	0.043 (2)	0.037 (2)	0.0295 (19)	0.0026 (17)	0.0056 (16)	0.0144 (16)
C31	0.044 (2)	0.039 (2)	0.042 (2)	0.0017 (17)	0.0086 (17)	0.0199 (18)
C32	0.056 (3)	0.051 (3)	0.052 (3)	0.017 (2)	0.013 (2)	0.031 (2)
C33	0.043 (2)	0.067 (3)	0.042 (2)	0.011 (2)	0.0090 (19)	0.025 (2)
C34	0.042 (2)	0.059 (3)	0.053 (3)	−0.007 (2)	0.0043 (19)	0.027 (2)
C35	0.049 (2)	0.042 (2)	0.047 (2)	0.0012 (18)	0.0069 (19)	0.0241 (19)
C36	0.060 (3)	0.100 (4)	0.079 (4)	0.027 (3)	0.006 (3)	0.049 (3)
C37	0.191 (9)	0.093 (5)	0.109 (6)	0.006 (6)	0.048 (6)	0.047 (5)
Cl5	0.259 (4)	0.1184 (19)	0.137 (2)	0.048 (2)	0.080 (2)	0.0351 (16)
Cl6	0.145 (2)	0.254 (4)	0.131 (2)	0.001 (2)	0.0345 (18)	0.055 (2)
Cl7	0.186 (3)	0.184 (3)	0.252 (4)	0.077 (3)	0.079 (3)	0.110 (3)
C38	0.133 (16)	0.078 (11)	0.28 (3)	0.045 (11)	−0.005 (17)	0.067 (15)
O6	0.108 (8)	0.135 (9)	0.110 (8)	−0.019 (6)	0.030 (6)	0.054 (7)

Geometric parameters (Å, º)

Cl1—C10	1.734 (6)	C16—H16	0.9300
Cl2—C14	1.721 (6)	C17—C18	1.376 (6)
Cl3—C25	1.738 (6)	C17—H17	0.9300
Cl4—C29	1.738 (6)	C18—C19	1.368 (6)
N1—C8	1.269 (5)	C19—C20	1.384 (6)
N1—O2	1.416 (4)	C19—H19	0.9300
N2—C23	1.267 (5)	C20—H20	0.9300
N2—O4	1.412 (4)	C21—H21A	0.9600
O1—C1	1.193 (4)	C21—H21B	0.9600
O2—C2	1.469 (4)	C21—H21C	0.9600
O3—C18	1.374 (5)	C22—C30	1.508 (5)
O3—C21	1.415 (7)	C22—C23	1.512 (6)
O4—C6	1.450 (5)	C22—H22	0.9800
O5—C33	1.357 (5)	C23—C24	1.482 (6)
O5—C36	1.410 (7)	C24—C29	1.391 (7)
C1—C2	1.542 (5)	C24—C25	1.399 (7)
C1—C6	1.545 (5)	C25—C26	1.385 (7)
C2—C3	1.527 (5)	C26—C27	1.358 (11)
C2—C7	1.542 (5)	C26—H26	0.9300
C3—C4	1.521 (6)	C27—C28	1.378 (11)
C3—H3A	0.9700	C27—H27	0.9300
C3—H3B	0.9700	C28—C29	1.388 (8)
C4—C5	1.503 (6)	C28—H28	0.9300
C4—H4A	0.9700	C30—C31	1.378 (5)
C4—H4B	0.9700	C30—C35	1.398 (5)
C5—C6	1.529 (6)	C31—C32	1.390 (6)
C5—H5A	0.9700	C31—H31	0.9300
C5—H5B	0.9700	C32—C33	1.380 (6)
C6—C22	1.561 (5)	C32—H32	0.9300
C7—C15	1.508 (5)	C33—C34	1.386 (6)
C7—C8	1.513 (5)	C34—C35	1.369 (6)
C7—H7	0.9800	C34—H34	0.9300
C8—C9	1.482 (6)	C35—H35	0.9300
C9—C10	1.391 (7)	C36—H36A	0.9600
C9—C14	1.405 (6)	C36—H36B	0.9600
C10—C11	1.388 (7)	C36—H36C	0.9600
C11—C12	1.357 (9)	C37—Cl7	1.693 (10)
C11—H11	0.9300	C37—Cl5	1.710 (9)
C12—C13	1.379 (9)	C37—Cl6	1.742 (10)
C12—H12	0.9300	C37—H37	0.9800
C13—C14	1.387 (7)	C38—O6	1.435 (10)
C13—H13	0.9300	C38—H38A	0.9600
C15—C16	1.371 (5)	C38—H38B	0.9600
C15—C20	1.393 (6)	C38—H38C	0.9600
C16—C17	1.392 (6)	O6—H6	0.8499
C8—N1—O2	109.4 (3)	O3—C18—C17	124.9 (4)
C23—N2—O4	108.9 (3)	C18—C19—C20	120.1 (4)
N1—O2—C2	108.5 (3)	C18—C19—H19	119.9
C18—O3—C21	118.6 (4)	C20—C19—H19	119.9
N2—O4—C6	109.1 (3)	C19—C20—C15	121.1 (4)
C33—O5—C36	118.0 (4)	C19—C20—H20	119.5
O1—C1—C2	122.3 (3)	C15—C20—H20	119.5
O1—C1—C6	121.1 (3)	O3—C21—H21A	109.5
C2—C1—C6	116.5 (3)	O3—C21—H21B	109.5
O2—C2—C3	107.1 (3)	H21A—C21—H21B	109.5
O2—C2—C1	106.3 (3)	O3—C21—H21C	109.5
C3—C2—C1	108.1 (3)	H21A—C21—H21C	109.5
O2—C2—C7	103.9 (3)	H21B—C21—H21C	109.5
C3—C2—C7	118.4 (3)	C30—C22—C23	113.6 (3)
C1—C2—C7	112.2 (3)	C30—C22—C6	117.5 (3)
C4—C3—C2	110.2 (3)	C23—C22—C6	98.1 (3)
C4—C3—H3A	109.6	C30—C22—H22	109.0
C2—C3—H3A	109.6	C23—C22—H22	109.0
C4—C3—H3B	109.6	C6—C22—H22	109.0
C2—C3—H3B	109.6	N2—C23—C24	120.6 (4)
H3A—C3—H3B	108.1	N2—C23—C22	115.4 (3)
C5—C4—C3	112.1 (4)	C24—C23—C22	124.0 (3)
C5—C4—H4A	109.2	C29—C24—C25	116.5 (4)
C3—C4—H4A	109.2	C29—C24—C23	120.0 (4)
C5—C4—H4B	109.2	C25—C24—C23	123.5 (4)
C3—C4—H4B	109.2	C26—C25—C24	122.2 (6)
H4A—C4—H4B	107.9	C26—C25—Cl3	117.6 (5)
C4—C5—C6	113.0 (3)	C24—C25—Cl3	120.3 (4)
C4—C5—H5A	109.0	C27—C26—C25	118.6 (7)
C6—C5—H5A	109.0	C27—C26—H26	120.7
C4—C5—H5B	109.0	C25—C26—H26	120.7
C6—C5—H5B	109.0	C26—C27—C28	122.3 (6)
H5A—C5—H5B	107.8	C26—C27—H27	118.9
O4—C6—C5	106.9 (3)	C28—C27—H27	118.9
O4—C6—C1	107.7 (3)	C27—C28—C29	118.0 (7)
C5—C6—C1	110.5 (3)	C27—C28—H28	121.0
O4—C6—C22	104.1 (3)	C29—C28—H28	121.0
C5—C6—C22	118.2 (3)	C28—C29—C24	122.4 (6)
C1—C6—C22	108.8 (3)	C28—C29—Cl4	118.2 (5)
C15—C7—C8	112.5 (3)	C24—C29—Cl4	119.3 (4)
C15—C7—C2	116.6 (3)	C31—C30—C35	117.9 (4)
C8—C7—C2	99.2 (3)	C31—C30—C22	120.2 (3)
C15—C7—H7	109.3	C35—C30—C22	121.9 (3)
C8—C7—H7	109.3	C30—C31—C32	121.6 (4)
C2—C7—H7	109.3	C30—C31—H31	119.2
N1—C8—C9	119.0 (4)	C32—C31—H31	119.2
N1—C8—C7	114.7 (3)	C33—C32—C31	119.7 (4)
C9—C8—C7	126.1 (3)	C33—C32—H32	120.1
C10—C9—C14	116.3 (4)	C31—C32—H32	120.1
C10—C9—C8	123.1 (4)	O5—C33—C32	125.5 (4)
C14—C9—C8	120.6 (4)	O5—C33—C34	115.4 (4)
C11—C10—C9	122.0 (5)	C32—C33—C34	119.1 (4)
C11—C10—Cl1	116.9 (4)	C35—C34—C33	120.9 (4)
C9—C10—Cl1	121.1 (4)	C35—C34—H34	119.5
C12—C11—C10	120.1 (6)	C33—C34—H34	119.5
C12—C11—H11	119.9	C34—C35—C30	120.8 (4)
C10—C11—H11	119.9	C34—C35—H35	119.6
C11—C12—C13	120.3 (5)	C30—C35—H35	119.6
C11—C12—H12	119.8	O5—C36—H36A	109.5
C13—C12—H12	119.8	O5—C36—H36B	109.5
C12—C13—C14	119.6 (6)	H36A—C36—H36B	109.5
C12—C13—H13	120.2	O5—C36—H36C	109.5
C14—C13—H13	120.2	H36A—C36—H36C	109.5
C13—C14—C9	121.6 (5)	H36B—C36—H36C	109.5
C13—C14—Cl2	118.5 (4)	Cl7—C37—Cl5	114.3 (5)
C9—C14—Cl2	119.8 (4)	Cl7—C37—Cl6	109.0 (5)
C16—C15—C20	117.7 (4)	Cl5—C37—Cl6	109.2 (6)
C16—C15—C7	120.7 (4)	Cl7—C37—H37	108.1
C20—C15—C7	121.6 (3)	Cl5—C37—H37	108.1
C15—C16—C17	121.5 (4)	Cl6—C37—H37	108.1
C15—C16—H16	119.2	O6—C38—H38A	109.5
C17—C16—H16	119.2	O6—C38—H38B	109.5
C18—C17—C16	119.6 (4)	H38A—C38—H38B	109.5
C18—C17—H17	120.2	O6—C38—H38C	109.5
C16—C17—H17	120.2	H38A—C38—H38C	109.5
C19—C18—O3	115.2 (4)	H38B—C38—H38C	109.5
C19—C18—C17	119.9 (4)	C38—O6—H6	124.1
C8—N1—O2—C2	12.2 (4)	C8—C7—C15—C20	−51.0 (5)
C23—N2—O4—C6	12.6 (4)	C2—C7—C15—C20	62.7 (5)
N1—O2—C2—C3	−146.1 (3)	C20—C15—C16—C17	−2.3 (6)
N1—O2—C2—C1	98.5 (3)	C7—C15—C16—C17	176.1 (4)
N1—O2—C2—C7	−20.1 (3)	C15—C16—C17—C18	1.0 (7)
O1—C1—C2—O2	−118.9 (4)	C21—O3—C18—C19	−175.1 (5)
C6—C1—C2—O2	62.3 (4)	C21—O3—C18—C17	4.7 (7)
O1—C1—C2—C3	126.4 (4)	C16—C17—C18—C19	0.7 (7)
C6—C1—C2—C3	−52.3 (4)	C16—C17—C18—O3	−179.2 (4)
O1—C1—C2—C7	−5.9 (5)	O3—C18—C19—C20	179.0 (4)
C6—C1—C2—C7	175.3 (3)	C17—C18—C19—C20	−0.9 (7)
O2—C2—C3—C4	−56.9 (4)	C18—C19—C20—C15	−0.5 (6)
C1—C2—C3—C4	57.3 (4)	C16—C15—C20—C19	2.1 (6)
C7—C2—C3—C4	−173.8 (3)	C7—C15—C20—C19	−176.3 (4)
C2—C3—C4—C5	−61.6 (5)	O4—C6—C22—C30	−103.2 (4)
C3—C4—C5—C6	56.1 (5)	C5—C6—C22—C30	15.2 (5)
N2—O4—C6—C5	−146.0 (3)	C1—C6—C22—C30	142.2 (3)
N2—O4—C6—C1	95.2 (3)	O4—C6—C22—C23	18.8 (4)
N2—O4—C6—C22	−20.2 (4)	C5—C6—C22—C23	137.2 (3)
C4—C5—C6—O4	−164.0 (3)	C1—C6—C22—C23	−95.8 (3)
C4—C5—C6—C1	−47.1 (4)	O4—N2—C23—C24	−179.9 (4)
C4—C5—C6—C22	79.2 (4)	O4—N2—C23—C22	1.4 (5)
O1—C1—C6—O4	−15.3 (5)	C30—C22—C23—N2	111.7 (4)
C2—C1—C6—O4	163.5 (3)	C6—C22—C23—N2	−13.1 (4)
O1—C1—C6—C5	−131.8 (4)	C30—C22—C23—C24	−67.0 (5)
C2—C1—C6—C5	47.0 (4)	C6—C22—C23—C24	168.1 (4)
O1—C1—C6—C22	97.0 (4)	N2—C23—C24—C29	113.7 (5)
C2—C1—C6—C22	−84.3 (4)	C22—C23—C24—C29	−67.6 (6)
O2—C2—C7—C15	−102.0 (3)	N2—C23—C24—C25	−65.9 (6)
C3—C2—C7—C15	16.5 (5)	C22—C23—C24—C25	112.8 (5)
C1—C2—C7—C15	143.6 (3)	C29—C24—C25—C26	0.8 (7)
O2—C2—C7—C8	19.0 (3)	C23—C24—C25—C26	−179.7 (5)
C3—C2—C7—C8	137.6 (3)	C29—C24—C25—Cl3	−179.9 (4)
C1—C2—C7—C8	−95.4 (3)	C23—C24—C25—Cl3	−0.3 (6)
O2—N1—C8—C9	176.4 (3)	C24—C25—C26—C27	0.4 (9)
O2—N1—C8—C7	1.6 (4)	Cl3—C25—C26—C27	−179.1 (5)
C15—C7—C8—N1	110.4 (4)	C25—C26—C27—C28	−1.6 (10)
C2—C7—C8—N1	−13.6 (4)	C26—C27—C28—C29	1.7 (10)
C15—C7—C8—C9	−63.9 (5)	C27—C28—C29—C24	−0.5 (9)
C2—C7—C8—C9	172.1 (4)	C27—C28—C29—Cl4	−177.3 (5)
N1—C8—C9—C10	−56.7 (6)	C25—C24—C29—C28	−0.7 (7)
C7—C8—C9—C10	117.4 (5)	C23—C24—C29—C28	179.7 (5)
N1—C8—C9—C14	122.8 (4)	C25—C24—C29—Cl4	176.1 (4)
C7—C8—C9—C14	−63.1 (5)	C23—C24—C29—Cl4	−3.5 (6)
C14—C9—C10—C11	1.5 (7)	C23—C22—C30—C31	130.6 (4)
C8—C9—C10—C11	−179.0 (4)	C6—C22—C30—C31	−115.8 (4)
C14—C9—C10—Cl1	−178.9 (3)	C23—C22—C30—C35	−50.9 (5)
C8—C9—C10—Cl1	0.6 (6)	C6—C22—C30—C35	62.7 (5)
C9—C10—C11—C12	0.2 (8)	C35—C30—C31—C32	−0.6 (6)
Cl1—C10—C11—C12	−179.4 (4)	C22—C30—C31—C32	178.0 (4)
C10—C11—C12—C13	−1.5 (9)	C30—C31—C32—C33	0.7 (6)
C11—C12—C13—C14	1.1 (9)	C36—O5—C33—C32	3.8 (7)
C12—C13—C14—C9	0.7 (8)	C36—O5—C33—C34	−175.4 (4)
C12—C13—C14—Cl2	−176.5 (4)	C31—C32—C33—O5	−179.9 (4)
C10—C9—C14—C13	−1.9 (6)	C31—C32—C33—C34	−0.6 (6)
C8—C9—C14—C13	178.6 (4)	O5—C33—C34—C35	179.9 (4)
C10—C9—C14—Cl2	175.3 (3)	C32—C33—C34—C35	0.6 (7)
C8—C9—C14—Cl2	−4.2 (6)	C33—C34—C35—C30	−0.5 (7)
C8—C7—C15—C16	130.7 (4)	C31—C30—C35—C34	0.5 (6)
C2—C7—C15—C16	−115.6 (4)	C22—C30—C35—C34	−178.0 (4)