Racemic 2,10-dibenz­yl­oxy-12-chloro-3,9-dimeth­oxy-5,8,13,13a-tetra­hydro-6H-dibenzo[a,g]quinolizine

The title compound, C₃₃H₃₂ClNO₄, prepared by methyl­ation of 12-chloro-2,10-dibenz­yl­oxy-9-hydroxy-3-methoxy­tetra­hydro­protoberberine with diazo­methane, contains a fused four-ring system in which the trans-fused rings both have half-chair conformations. No significant inter­molecular inter­actions are observed in the structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.063
• wR factor = 0.177
• Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT213_ALERT_2_B Atom C21     has ADP max/min Ratio .............       4.60 prolat
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C20
PLAT331_ALERT_2_B Small Average Phenyl C-C Dist.   C20    -C25           1.35 Ang.

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.705     0.930
            Tmin' and Tmax expected:      0.914     0.934
            RR' =      0.774
            Please check that your absorption correction is appropriate.
SHFSU01_ALERT_2_C  The absolute value of parameter shift to su ratio > 0.05
            Absolute value of the parameter shift to su ratio given   0.087
            Additional refinement cycles may be required.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.77
PLAT080_ALERT_2_C Maximum Shift/Error ............................       0.09
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT213_ALERT_2_C Atom C22     has ADP max/min Ratio .............       3.40 prolat
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.00 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C28    -   C29     ..       5.54 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C28    -   C33     ..       5.22 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C21
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C30
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C28
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C28    -C33           1.36 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  14 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker,2000); cell refinement: SAINT (Bruker,2000); data reduction: SHELXTL (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2,10-dibenzyloxy-12-chloro-3,9-dimethoxy-5,8,13,13a- tetrahydro-6H-dibenzo[a,g]quinolizine

Crystal data

C33H32ClNO4	F(000) = 2288
Mr = 542.05	Dx = 1.262 Mg m^−3
Monoclinic, C2/c	Melting point: 422 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 20.4833 (18) Å	Cell parameters from 3475 reflections
b = 21.6089 (18) Å	θ = 5.0–44.9°
c = 16.0523 (14) Å	µ = 0.17 mm^−1
β = 126.549 (2)°	T = 293 K
V = 5707.9 (9) Å^3	Block, yellow
Z = 8	0.51 × 0.42 × 0.40 mm

Data collection

Bruker SMART CCD area-detector diffractometer	6226 independent reflections
Radiation source: fine-focus sealed tube	3798 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
φ and ω scans	θmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −26→22
Tmin = 0.705, Tmax = 0.930	k = −27→25
16679 measured reflections	l = −13→20

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.177	H-atom parameters constrained
S = 0.96	w = 1/[σ^2(Fo^2) + (0.0924P)^2] where P = (Fo^2 + 2Fc^2)/3
6226 reflections	(Δ/σ)max = 0.087
366 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.33 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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

15.1676 (0.0195)x + 13.7611(0.0228) y - 4.3087 (0.0216) z=27.2131(0.0169)

* -0.0087 (0.0020) C28 * 0.0045 (0.0024) C29 * 0.0051 (0.0028) C30 * -0.0107 (0.0028) C31 * 0.0063 (0.0024) C32 * 0.0035 (0.0020) C33

Rms deviation of fitted atoms = 0.0069

-7.6364 (0.0472)x + 13.2850(0.0326) y + 12.5264 (0.0202)z =15.1988 (0.0544)

Angle to previous plane (with approximate e.s.d.) = 74.65 (0.14)

* 0.0105 (0.0032) C20 * -0.0074 (0.0047) C21 * -0.0078 (0.0050) C22 * 0.0202 (0.0040) C23 * -0.0169 (0.0032) C24 * 0.0016 (0.0029) C25

Rms deviation of fitted atoms = 0.0124

16.9152 (0.0113)x - 1.8882(0.0201)y - 15.0788 (0.0054)z =1.7426(0.0258)

Angle to previous plane (with approximate e.s.d.) = 41.51 (0.17)

* 0.0116 (0.0017) C9 * -0.0010 (0.0017) C10 * -0.0079 (0.0017) C11 * 0.0063 (0.0016) C12 * -0.0134 (0.0017) C17 * 0.0044 (0.0016) C18

Rms deviation of fitted atoms = 0.0085

-10.8629 (0.0199) x + 11.1742 (0.0354)y + 13.7331(0.0162)z =10.9624(0.0308)

Angle to previous plane (with approximate e.s.d.) = 30.97 (0.12)

* 0.0037 (0.0007) C5 * -0.0039 (0.0007) C14 * 0.0082 (0.0015) C15 * -0.0080 (0.0015) C16 0.2671 (0.0044) N7 - 0.4964 (0.0052) C6

Rms deviation of fitted atoms = 0.0063

-11.0853(0.0168) x + 11.3381(0.0181)y + 13.6474(0.0084)z =10.9062(0.0217)

Angle to previous plane (with approximate e.s.d.) = 1.13 (0.21)

* -0.0019 (0.0017) C1 * -0.0022 (0.0017) C2 * 0.0054 (0.0017) C3 * -0.0044 (0.0018) C4 * 0.0030 (0.0016) C15 * 0.0002 (0.0017) C16

Rms deviation of fitted atoms = 0.0033

16.9152(0.0113) x - 1.8882 (0.0201)y - 15.0788(0.0054)z =1.7426(0.0258)

Angle to previous plane (with approximate e.s.d.) = 30.81 (0.09)

* 0.0116 (0.0017) C9 * -0.0010 (0.0017) C10 * -0.0079 (0.0017) C11 * 0.0063 (0.0016) C12 * -0.0134 (0.0017) C17 * 0.0044 (0.0016) C18

Rms deviation of fitted atoms = 0.0085

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
Cl	1.03774 (4)	1.09641 (3)	0.90831 (5)	0.0657 (2)
O1	1.19607 (10)	0.90460 (8)	1.11709 (13)	0.0676 (5)
O2	1.06818 (11)	0.82930 (8)	0.98098 (14)	0.0705 (5)
O3	0.66678 (10)	1.10771 (9)	0.42038 (14)	0.0794 (6)
O4	0.53848 (10)	1.05153 (9)	0.36682 (13)	0.0695 (5)
N7	0.84259 (11)	0.90284 (8)	0.74953 (15)	0.0545 (5)
C1	0.75440 (13)	1.03225 (10)	0.55417 (17)	0.0476 (5)
H1	0.8010	1.0536	0.5740	0.057*
C2	0.68022 (14)	1.05509 (11)	0.47500 (17)	0.0522 (6)
C3	0.60890 (14)	1.02331 (11)	0.44409 (18)	0.0533 (6)
C4	0.61610 (15)	0.96945 (12)	0.49381 (19)	0.0563 (6)
C5	0.69690 (15)	0.88684 (12)	0.6282 (2)	0.0693 (8)
H5A	0.6872	0.8955	0.6793	0.083*
H5B	0.6553	0.8583	0.5778	0.083*
C6	0.77916 (15)	0.85759 (12)	0.6806 (2)	0.0693 (8)
H6A	0.7837	0.8219	0.7205	0.083*
H6B	0.7860	0.8436	0.6288	0.083*
C8	0.92052 (16)	0.87195 (12)	0.8126 (2)	0.0612 (7)
C9	1.06352 (14)	0.89219 (10)	0.96494 (18)	0.0534 (6)
C10	1.12769 (14)	0.93120 (11)	1.03296 (18)	0.0540 (6)
C11	1.11841 (14)	0.99458 (11)	1.01508 (18)	0.0540 (6)
H11	1.1606	1.0216	1.0600	0.065*
C12	1.04563 (14)	1.01670 (10)	0.92968 (17)	0.0489 (5)
C13	0.90082 (13)	1.00399 (10)	0.76794 (17)	0.0479 (5)
H13A	0.9120	1.0340	0.7331	0.058*
H13B	0.8725	1.0252	0.7911	0.058*
C14	0.84592 (13)	0.95368 (10)	0.69120 (17)	0.0469 (5)
H14	0.8708	0.9378	0.6589	0.056*
C15	0.76219 (13)	0.97748 (10)	0.60642 (16)	0.0460 (5)
C16	0.69133 (14)	0.94619 (11)	0.57454 (19)	0.0518 (6)
C17	0.98993 (14)	0.91580 (10)	0.88105 (18)	0.0507 (6)
C18	0.97998 (13)	0.97912 (10)	0.86085 (17)	0.0461 (5)
C19	0.73114 (15)	1.14429 (13)	0.4454 (2)	0.0726 (8)
H19A	0.7691	1.1204	0.4410	0.087*
H19B	0.7595	1.1598	0.5156	0.087*
C20	0.69804 (16)	1.19715 (12)	0.3701 (2)	0.0664 (7)
C21	0.6184 (2)	1.2105 (2)	0.3057 (4)	0.119 (3)
H21	0.5815	1.1865	0.3074	0.124*
C22	0.5904 (3)	1.2596 (3)	0.2370 (5)	0.127 (4)
H22	0.5350	1.2679	0.1929	0.130*
C23	0.6416 (3)	1.29480 (18)	0.2331 (3)	0.1180 (14)
H23	0.6230	1.3289	0.1892	0.122*
C24	0.7201 (3)	1.28028 (17)	0.2933 (3)	0.1080 (12)
H24	0.7562	1.3029	0.2882	0.130*
C25	0.74877 (19)	1.23216 (15)	0.3634 (3)	0.0903 (10)
H25	0.8042	1.2239	0.4066	0.108*
C26	0.46454 (15)	1.02098 (15)	0.3301 (2)	0.0822 (9)
H26A	0.4634	0.9813	0.3023	0.123*
H26B	0.4196	1.0455	0.2768	0.123*
H26C	0.4606	1.0155	0.3863	0.123*
C27	1.27051 (15)	0.93765 (13)	1.1696 (2)	0.0728 (8)
H27A	1.2685	0.9737	1.2040	0.087*
H27B	1.2807	0.9514	1.1207	0.087*
C28	1.33600 (14)	0.89479 (11)	1.2471 (2)	0.0568 (6)
C29	1.3690 (2)	0.85104 (17)	1.2202 (3)	0.0929 (10)
H29	1.3525	0.8487	1.1524	0.111*
C30	1.4279 (2)	0.80974 (18)	1.2957 (4)	0.1152 (13)
H30	1.4504	0.7800	1.2779	0.128*
C31	1.4515 (2)	0.81338 (18)	1.3938 (4)	0.1018 (12)
H31	1.4895	0.7854	1.4431	0.122*
C32	1.42108 (19)	0.85657 (16)	1.4213 (3)	0.0888 (10)
H32	1.4387	0.8594	1.4896	0.107*
C33	1.36345 (16)	0.89685 (12)	1.3474 (2)	0.0683 (7)
H33	1.3424	0.9267	1.3671	0.082*
C34	1.1295 (2)	0.79681 (14)	0.9841 (3)	0.0951 (10)
H34A	1.1061	0.7615	0.9392	0.123*
H34B	1.1704	0.7833	1.0538	0.123*
H34C	1.1536	0.8235	0.9615	0.123*
H4	0.5676 (14)	0.9475 (11)	0.4693 (18)	0.060 (7)*
H8A	0.9205 (15)	0.8414 (12)	0.855 (2)	0.068 (7)*
H8B	0.9368 (15)	0.8515 (12)	0.774 (2)	0.069 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.0634 (4)	0.0405 (3)	0.0764 (5)	−0.0063 (3)	0.0325 (4)	0.0030 (3)
O1	0.0522 (10)	0.0613 (11)	0.0614 (11)	−0.0078 (8)	0.0187 (9)	0.0206 (8)
O2	0.0623 (11)	0.0461 (10)	0.0817 (13)	0.0004 (8)	0.0313 (10)	0.0218 (9)
O3	0.0514 (10)	0.0816 (14)	0.0710 (12)	−0.0103 (9)	0.0179 (9)	0.0346 (10)
O4	0.0439 (10)	0.0803 (13)	0.0620 (11)	−0.0062 (9)	0.0194 (9)	0.0130 (9)
N7	0.0523 (11)	0.0412 (11)	0.0561 (12)	−0.0081 (9)	0.0248 (10)	0.0083 (9)
C1	0.0447 (13)	0.0511 (13)	0.0464 (13)	−0.0080 (10)	0.0268 (11)	0.0007 (10)
C2	0.0517 (14)	0.0551 (14)	0.0452 (13)	−0.0056 (11)	0.0263 (12)	0.0063 (11)
C3	0.0477 (13)	0.0607 (15)	0.0454 (13)	−0.0061 (11)	0.0245 (11)	−0.0004 (11)
C4	0.0475 (14)	0.0590 (15)	0.0581 (15)	−0.0137 (12)	0.0291 (13)	−0.0021 (12)
C5	0.0582 (16)	0.0582 (16)	0.0769 (19)	−0.0160 (13)	0.0323 (14)	0.0085 (13)
C6	0.0650 (17)	0.0469 (15)	0.0735 (18)	−0.0136 (12)	0.0291 (14)	0.0077 (12)
C8	0.0637 (16)	0.0395 (13)	0.0635 (17)	−0.0066 (12)	0.0287 (14)	0.0072 (12)
C9	0.0581 (14)	0.0429 (13)	0.0518 (14)	−0.0036 (11)	0.0287 (12)	0.0119 (10)
C10	0.0542 (14)	0.0542 (14)	0.0482 (14)	−0.0033 (11)	0.0275 (12)	0.0133 (11)
C11	0.0535 (14)	0.0518 (14)	0.0521 (14)	−0.0093 (11)	0.0289 (12)	0.0017 (11)
C12	0.0562 (14)	0.0398 (12)	0.0517 (14)	−0.0034 (10)	0.0327 (12)	0.0053 (10)
C13	0.0519 (13)	0.0404 (12)	0.0484 (13)	−0.0047 (10)	0.0282 (11)	0.0033 (10)
C14	0.0525 (13)	0.0408 (12)	0.0491 (13)	−0.0037 (10)	0.0311 (11)	0.0029 (10)
C15	0.0500 (13)	0.0449 (12)	0.0442 (13)	−0.0056 (10)	0.0287 (11)	−0.0025 (10)
C16	0.0530 (14)	0.0492 (13)	0.0534 (14)	−0.0101 (11)	0.0318 (12)	−0.0006 (11)
C17	0.0561 (14)	0.0431 (13)	0.0509 (14)	−0.0036 (10)	0.0308 (12)	0.0068 (10)
C18	0.0510 (13)	0.0435 (12)	0.0460 (13)	−0.0031 (10)	0.0302 (11)	0.0061 (10)
C19	0.0569 (16)	0.0638 (17)	0.083 (2)	−0.0004 (13)	0.0338 (15)	0.0218 (14)
C20	0.0639 (17)	0.0572 (16)	0.0805 (19)	0.0070 (13)	0.0443 (15)	0.0196 (13)
C21	0.089 (3)	0.126 (5)	0.196 (6)	0.054 (3)	0.100 (3)	0.137 (5)
C22	0.104 (3)	0.158 (6)	0.199 (8)	0.086 (4)	0.115 (4)	0.148 (6)
C23	0.127 (3)	0.109 (3)	0.139 (3)	0.039 (3)	0.091 (3)	0.076 (3)
C24	0.113 (3)	0.089 (3)	0.136 (3)	−0.004 (2)	0.082 (3)	0.041 (2)
C25	0.075 (2)	0.082 (2)	0.108 (3)	−0.0010 (17)	0.0517 (19)	0.0312 (19)
C26	0.0470 (15)	0.109 (2)	0.077 (2)	−0.0103 (15)	0.0297 (14)	0.0095 (17)
C27	0.0579 (16)	0.0665 (18)	0.0680 (18)	−0.0119 (13)	0.0234 (14)	0.0127 (13)
C28	0.0510 (14)	0.0561 (15)	0.0580 (16)	−0.0061 (11)	0.0295 (13)	0.0004 (12)
C29	0.094 (2)	0.103 (3)	0.088 (2)	0.002 (2)	0.058 (2)	−0.008 (2)
C30	0.103 (3)	0.101 (3)	0.147 (4)	0.031 (2)	0.078 (3)	−0.009 (3)
C31	0.067 (2)	0.090 (3)	0.113 (3)	0.0219 (18)	0.035 (2)	0.015 (2)
C32	0.075 (2)	0.087 (2)	0.071 (2)	0.0041 (18)	0.0259 (17)	0.0098 (17)
C33	0.0618 (16)	0.0637 (17)	0.0673 (19)	0.0048 (13)	0.0320 (15)	0.0026 (13)
C34	0.102 (3)	0.0593 (19)	0.121 (3)	0.0042 (17)	0.065 (2)	0.0042 (18)

Geometric parameters (Å, º)

Cl—C12	1.745 (2)	C14—C15	1.509 (3)
O1—C10	1.365 (3)	C14—H14	0.9800
O1—C27	1.419 (3)	C15—C16	1.393 (3)
O2—C9	1.376 (3)	C17—C18	1.393 (3)
O2—C34	1.413 (3)	C19—C20	1.499 (3)
O3—C2	1.360 (3)	C19—H19A	0.9700
O3—C19	1.376 (3)	C19—H19B	0.9700
O4—C3	1.364 (3)	C20—C25	1.341 (4)
O4—C26	1.419 (3)	C20—C21	1.344 (4)
N7—C8	1.447 (3)	C21—C22	1.384 (5)
N7—C6	1.468 (3)	C21—H21	0.9300
N7—C14	1.471 (3)	C22—C23	1.327 (5)
C1—C2	1.367 (3)	C22—H22	0.9300
C1—C15	1.404 (3)	C23—C24	1.329 (5)
C1—H1	0.9300	C23—H23	0.9300
C2—C3	1.410 (3)	C24—C25	1.380 (4)
C3—C4	1.369 (3)	C24—H24	0.9300
C4—C16	1.389 (3)	C25—H25	0.9300
C4—H4	0.95 (2)	C26—H26A	0.9600
C5—C6	1.503 (4)	C26—H26B	0.9600
C5—C16	1.511 (3)	C26—H26C	0.9600
C5—H5A	0.9700	C27—C28	1.489 (4)
C5—H5B	0.9700	C27—H27A	0.9700
C6—H6A	0.9700	C27—H27B	0.9700
C6—H6B	0.9700	C28—C33	1.354 (4)
C8—C17	1.506 (3)	C28—C29	1.372 (4)
C8—H8A	0.95 (3)	C29—C30	1.407 (5)
C8—H8B	0.97 (3)	C29—H29	0.9300
C9—C10	1.386 (3)	C30—C31	1.347 (5)
C9—C17	1.389 (3)	C30—H30	0.9300
C10—C11	1.389 (3)	C31—C32	1.335 (5)
C11—C12	1.377 (3)	C31—H31	0.9300
C11—H11	0.9300	C32—C33	1.375 (4)
C12—C18	1.385 (3)	C32—H32	0.9300
C13—C18	1.504 (3)	C33—H33	0.9300
C13—C14	1.521 (3)	C34—H34A	0.9600
C13—H13A	0.9700	C34—H34B	0.9600
C13—H13B	0.9700	C34—H34C	0.9600
C10—O1—C27	118.81 (18)	C9—C17—C18	120.7 (2)
C9—O2—C34	117.3 (2)	C9—C17—C8	119.0 (2)
C2—O3—C19	120.08 (19)	C18—C17—C8	120.3 (2)
C3—O4—C26	117.3 (2)	C12—C18—C17	116.9 (2)
C8—N7—C6	109.42 (19)	C12—C18—C13	122.88 (19)
C8—N7—C14	109.85 (19)	C17—C18—C13	120.3 (2)
C6—N7—C14	111.92 (18)	O3—C19—C20	107.9 (2)
C2—C1—C15	121.9 (2)	O3—C19—H19A	110.1
C2—C1—H1	119.1	C20—C19—H19A	110.1
C15—C1—H1	119.1	O3—C19—H19B	110.1
O3—C2—C1	126.0 (2)	C20—C19—H19B	110.1
O3—C2—C3	114.3 (2)	H19A—C19—H19B	108.4
C1—C2—C3	119.8 (2)	C25—C20—C21	117.4 (3)
O4—C3—C4	126.8 (2)	C25—C20—C19	119.6 (2)
O4—C3—C2	114.5 (2)	C21—C20—C19	122.9 (3)
C4—C3—C2	118.7 (2)	C20—C21—C22	121.0 (3)
C3—C4—C16	121.8 (2)	C20—C21—H21	119.5
C3—C4—H4	117.4 (14)	C22—C21—H21	119.5
C16—C4—H4	120.8 (14)	C23—C22—C21	120.9 (4)
C6—C5—C16	110.8 (2)	C23—C22—H22	119.6
C6—C5—H5A	109.5	C21—C22—H22	119.6
C16—C5—H5A	109.5	C22—C23—C24	118.5 (3)
C6—C5—H5B	109.5	C22—C23—H23	120.7
C16—C5—H5B	109.5	C24—C23—H23	120.7
H5A—C5—H5B	108.1	C23—C24—C25	121.0 (3)
N7—C6—C5	109.6 (2)	C23—C24—H24	119.5
N7—C6—H6A	109.7	C25—C24—H24	119.5
C5—C6—H6A	109.7	C20—C25—C24	121.1 (3)
N7—C6—H6B	109.7	C20—C25—H25	119.4
C5—C6—H6B	109.7	C24—C25—H25	119.5
H6A—C6—H6B	108.2	O4—C26—H26A	109.5
N7—C8—C17	112.9 (2)	O4—C26—H26B	109.5
N7—C8—H8A	110.5 (15)	H26A—C26—H26B	109.5
C17—C8—H8A	108.4 (16)	O4—C26—H26C	109.5
N7—C8—H8B	114.8 (15)	H26A—C26—H26C	109.5
C17—C8—H8B	102.7 (15)	H26B—C26—H26C	109.5
H8A—C8—H8B	107 (2)	O1—C27—C28	107.3 (2)
O2—C9—C10	121.7 (2)	O1—C27—H27A	110.3
O2—C9—C17	117.3 (2)	C28—C27—H27A	110.3
C10—C9—C17	120.9 (2)	O1—C27—H27B	110.2
O1—C10—C9	117.1 (2)	C28—C27—H27B	110.2
O1—C10—C11	123.6 (2)	H27A—C27—H27B	108.5
C9—C10—C11	119.2 (2)	C33—C28—C29	117.6 (3)
C12—C11—C10	118.8 (2)	C33—C28—C27	120.2 (2)
C12—C11—H11	120.6	C29—C28—C27	122.2 (3)
C10—C11—H11	120.6	C28—C29—C30	119.8 (3)
C11—C12—C18	123.5 (2)	C28—C29—H29	120.1
C11—C12—Cl	117.19 (17)	C30—C29—H29	120.1
C18—C12—Cl	119.31 (17)	C31—C30—C29	119.8 (3)
C18—C13—C14	112.84 (18)	C31—C30—H30	120.1
C18—C13—H13A	109.0	C29—C30—H30	120.1
C14—C13—H13A	109.0	C32—C31—C30	121.0 (3)
C18—C13—H13B	109.0	C32—C31—H31	119.5
C14—C13—H13B	109.0	C30—C31—H31	119.5
H13A—C13—H13B	107.8	C31—C32—C33	119.1 (3)
N7—C14—C15	111.71 (18)	C31—C32—H32	120.4
N7—C14—C13	108.09 (18)	C33—C32—H32	120.4
C15—C14—C13	112.45 (18)	C28—C33—C32	122.7 (3)
N7—C14—H14	108.2	C28—C33—H33	118.6
C15—C14—H14	108.2	C32—C33—H33	118.6
C13—C14—H14	108.2	O2—C34—H34A	109.5
C16—C15—C1	117.8 (2)	O2—C34—H34B	109.5
C16—C15—C14	122.8 (2)	H34A—C34—H34B	109.5
C1—C15—C14	119.33 (19)	O2—C34—H34C	109.5
C4—C16—C15	120.1 (2)	H34A—C34—H34C	109.5
C4—C16—C5	120.3 (2)	H34B—C34—H34C	109.5
C15—C16—C5	119.6 (2)
C19—O3—C2—C1	−2.1 (4)	C14—C15—C16—C4	−178.0 (2)
C19—O3—C2—C3	177.6 (2)	C1—C15—C16—C5	179.7 (2)
C15—C1—C2—O3	179.7 (2)	C14—C15—C16—C5	2.0 (4)
C15—C1—C2—C3	0.1 (4)	C6—C5—C16—C4	157.7 (2)
C26—O4—C3—C4	−3.1 (4)	C6—C5—C16—C15	−22.2 (4)
C26—O4—C3—C2	178.2 (2)	O2—C9—C17—C18	178.8 (2)
O3—C2—C3—O4	−1.8 (3)	C10—C9—C17—C18	2.7 (4)
C1—C2—C3—O4	177.9 (2)	O2—C9—C17—C8	−0.6 (4)
O3—C2—C3—C4	179.4 (2)	C10—C9—C17—C8	−176.7 (2)
C1—C2—C3—C4	−0.9 (4)	N7—C8—C17—C9	162.3 (2)
O4—C3—C4—C16	−177.5 (2)	N7—C8—C17—C18	−17.2 (4)
C2—C3—C4—C16	1.1 (4)	C11—C12—C18—C17	0.0 (3)
C8—N7—C6—C5	170.5 (2)	Cl—C12—C18—C17	179.34 (17)
C14—N7—C6—C5	−67.5 (3)	C11—C12—C18—C13	179.9 (2)
C16—C5—C6—N7	53.6 (3)	Cl—C12—C18—C13	−0.7 (3)
C6—N7—C8—C17	176.4 (2)	C9—C17—C18—C12	−1.9 (3)
C14—N7—C8—C17	53.2 (3)	C8—C17—C18—C12	177.6 (2)
C34—O2—C9—C10	−60.5 (3)	C9—C17—C18—C13	178.2 (2)
C34—O2—C9—C17	123.4 (3)	C8—C17—C18—C13	−2.4 (4)
C27—O1—C10—C9	160.1 (2)	C14—C13—C18—C12	166.5 (2)
C27—O1—C10—C11	−22.6 (4)	C14—C13—C18—C17	−13.6 (3)
O2—C9—C10—O1	−0.1 (4)	C2—O3—C19—C20	178.0 (2)
C17—C9—C10—O1	175.9 (2)	O3—C19—C20—C25	−165.9 (3)
O2—C9—C10—C11	−177.5 (2)	O3—C19—C20—C21	12.1 (5)
C17—C9—C10—C11	−1.5 (4)	C25—C20—C21—C22	−1.5 (9)
O1—C10—C11—C12	−177.6 (2)	C19—C20—C21—C22	−179.5 (6)
C9—C10—C11—C12	−0.4 (4)	C20—C21—C22—C23	−0.3 (11)
C10—C11—C12—C18	1.2 (4)	C21—C22—C23—C24	3.1 (10)
C10—C11—C12—Cl	−178.24 (18)	C22—C23—C24—C25	−4.2 (8)
C8—N7—C14—C15	166.6 (2)	C21—C20—C25—C24	0.4 (6)
C6—N7—C14—C15	44.8 (3)	C19—C20—C25—C24	178.5 (3)
C8—N7—C14—C13	−69.2 (2)	C23—C24—C25—C20	2.5 (6)
C6—N7—C14—C13	169.1 (2)	C10—O1—C27—C28	−171.9 (2)
C18—C13—C14—N7	47.9 (2)	O1—C27—C28—C33	−97.7 (3)
C18—C13—C14—C15	171.68 (18)	O1—C27—C28—C29	80.3 (3)
C2—C1—C15—C16	0.5 (3)	C33—C28—C29—C30	1.2 (5)
C2—C1—C15—C14	178.3 (2)	C27—C28—C29—C30	−176.9 (3)
N7—C14—C15—C16	−12.7 (3)	C28—C29—C30—C31	0.0 (6)
C13—C14—C15—C16	−134.4 (2)	C29—C30—C31—C32	−1.5 (6)
N7—C14—C15—C1	169.7 (2)	C30—C31—C32—C33	1.5 (6)
C13—C14—C15—C1	48.0 (3)	C29—C28—C33—C32	−1.2 (4)
C3—C4—C16—C15	−0.6 (4)	C27—C28—C33—C32	176.9 (3)
C3—C4—C16—C5	179.5 (2)	C31—C32—C33—C28	−0.2 (5)
C1—C15—C16—C4	−0.3 (3)