3-(3,5-Dimethoxy­phen­yl)-1-(3-nitro­phen­yl)prop-2-enone

In the title mol­ecule, C₁₇H₁₅NO₅, all bond lengths and angles show normal values. There are two molecules in the asymmetric unit. The dihedral angles between the benzene rings are 9.0 (2) and 11.7 (2)° in the two molecules. The crystal packing is stabilized by van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.052
• wR factor = 0.142
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         43 Perc.
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ......       3.12 Sigma
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.31
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.10
PLAT432_ALERT_2_C Short Inter X...Y Contact  O8     ..  C33     ..       3.01 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   3 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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.

3-(3,5-Dimethoxyphenyl)-1-(3-nitrophenyl)-prop-2-enone

Crystal data

C17H15NO5	F(000) = 1312
Mr = 313.30	Dx = 1.388 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3627 reflections
a = 8.2658 (3) Å	θ = 4.2–26°
b = 15.8334 (4) Å	µ = 0.10 mm^−1
c = 22.9084 (7) Å	T = 298 K
β = 90.747 (2)°	Block, yellow
V = 2997.90 (16) Å^3	0.28 × 0.17 × 0.06 mm
Z = 8

Data collection

Bruker SMART APEX area-detector diffractometer	5873 independent reflections
Radiation source: fine-focus sealed tube	2540 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
ω scans	θmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
Tmin = 0.975, Tmax = 0.991	k = −17→19
16559 measured reflections	l = −24→28

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.142	w = 1/[σ^2(Fo^2) + (0.0642P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.86	(Δ/σ)max < 0.001
5873 reflections	Δρmax = 0.16 e Å^−3
420 parameters	Δρmin = −0.17 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00053 (17)

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
O1	0.3419 (3)	0.76125 (11)	0.45129 (9)	0.0801 (6)
O9	−0.2287 (2)	0.66776 (10)	0.70541 (7)	0.0695 (6)
O6	0.1115 (3)	1.05383 (11)	0.57107 (8)	0.0783 (6)
O5	0.5112 (3)	1.26091 (11)	0.39296 (8)	0.0786 (6)
O4	0.3680 (3)	1.28399 (11)	0.46961 (8)	0.0756 (6)
C20	0.3957 (3)	1.14522 (14)	0.43813 (10)	0.0477 (6)
O8	1.0258 (3)	0.17443 (11)	0.11923 (8)	0.0846 (7)
C30	−0.0541 (3)	0.62676 (15)	0.63220 (11)	0.0552 (7)
H30	−0.0792	0.5710	0.6412	0.066*
C19	0.3078 (3)	1.11628 (13)	0.48438 (10)	0.0484 (6)
H19	0.2718	1.1538	0.5126	0.058*
C27	0.0182 (3)	0.79292 (14)	0.60388 (10)	0.0468 (6)
C18	0.2725 (3)	1.03032 (14)	0.48882 (10)	0.0473 (6)
O3	0.6845 (3)	0.55979 (11)	0.25462 (8)	0.0932 (8)
C6	0.4716 (3)	0.47821 (15)	0.38058 (11)	0.0618 (8)
H6	0.4787	0.4204	0.3737	0.074*
C11	0.7495 (3)	0.23442 (15)	0.26198 (10)	0.0534 (7)
H11	0.6866	0.2460	0.2944	0.064*
O7	0.7436 (2)	0.09255 (11)	0.28926 (7)	0.0745 (6)
C3	0.4476 (3)	0.64726 (14)	0.40099 (11)	0.0500 (7)
C1	0.5430 (3)	0.53444 (15)	0.34197 (10)	0.0524 (7)
C24	0.1734 (3)	1.00151 (15)	0.53930 (11)	0.0537 (7)
C13	0.8876 (3)	0.13399 (15)	0.20226 (11)	0.0564 (7)
H13	0.9183	0.0787	0.1945	0.068*
O2	0.5079 (3)	0.78752 (11)	0.38154 (9)	0.0792 (6)
O10	0.1313 (2)	0.58380 (10)	0.55595 (8)	0.0770 (6)
C32	−0.0893 (3)	0.77556 (14)	0.64908 (10)	0.0501 (7)
H32	−0.1367	0.8194	0.6697	0.060*
N2	0.4269 (3)	1.23669 (13)	0.43343 (10)	0.0561 (6)
N1	0.4316 (3)	0.73879 (13)	0.41185 (10)	0.0600 (6)
C4	0.3778 (3)	0.59260 (16)	0.43954 (11)	0.0608 (7)
H4	0.3232	0.6125	0.4720	0.073*
C2	0.5295 (3)	0.62085 (14)	0.35283 (10)	0.0533 (7)
H2	0.5755	0.6599	0.3277	0.064*
C10	0.7968 (3)	0.29933 (14)	0.22561 (11)	0.0495 (6)
C7	0.6363 (4)	0.50714 (16)	0.28914 (12)	0.0626 (8)
C14	0.9343 (3)	0.19920 (16)	0.16561 (11)	0.0580 (7)
C26	0.0530 (3)	0.88188 (14)	0.59015 (11)	0.0529 (7)
H26	0.0013	0.9223	0.6127	0.063*
C31	−0.1242 (3)	0.69236 (15)	0.66273 (10)	0.0517 (7)
C9	0.7538 (3)	0.38761 (15)	0.23726 (11)	0.0575 (7)
H9	0.7895	0.4274	0.2105	0.069*
C8	0.6702 (3)	0.41676 (15)	0.28144 (11)	0.0634 (8)
H8	0.6312	0.3787	0.3088	0.076*
C15	0.8902 (3)	0.28168 (15)	0.17683 (11)	0.0553 (7)
H15	0.9225	0.3250	0.1521	0.066*
C12	0.7956 (3)	0.15210 (15)	0.25014 (10)	0.0524 (7)
C23	0.3298 (3)	0.97691 (15)	0.44569 (11)	0.0583 (7)
H23	0.3080	0.9194	0.4479	0.070*
C21	0.4524 (3)	1.09228 (16)	0.39531 (11)	0.0580 (7)
H21	0.5119	1.1133	0.3643	0.070*
C22	0.4185 (4)	1.00732 (16)	0.39961 (11)	0.0638 (8)
H22	0.4556	0.9703	0.3713	0.077*
C29	0.0530 (3)	0.64459 (15)	0.58840 (11)	0.0569 (7)
C25	0.1498 (3)	0.91033 (15)	0.54915 (11)	0.0557 (7)
H25	0.2045	0.8719	0.5259	0.067*
C28	0.0904 (3)	0.72742 (14)	0.57395 (11)	0.0544 (7)
H28	0.1634	0.7388	0.5444	0.065*
C5	0.3909 (4)	0.50699 (16)	0.42870 (11)	0.0696 (8)
H5	0.3446	0.4685	0.4542	0.083*
C34	−0.2945 (4)	0.73100 (16)	0.74207 (12)	0.0700 (8)
H34A	−0.2082	0.7612	0.7612	0.105*
H34B	−0.3617	0.7050	0.7708	0.105*
H34C	−0.3580	0.7696	0.7190	0.105*
C16	0.7899 (4)	0.00696 (15)	0.28047 (12)	0.0889 (11)
H16A	0.7474	−0.0125	0.2437	0.133*
H16B	0.7478	−0.0273	0.3113	0.133*
H16C	0.9058	0.0029	0.2805	0.133*
C17	1.0832 (4)	0.23691 (17)	0.08058 (12)	0.0817 (10)
H17A	0.9931	0.2659	0.0629	0.123*
H17B	1.1465	0.2107	0.0508	0.123*
H17C	1.1491	0.2766	0.1018	0.123*
C33	0.1007 (4)	0.49751 (14)	0.57025 (12)	0.0723 (9)
H33A	0.1278	0.4878	0.6106	0.108*
H33B	0.1653	0.4616	0.5462	0.108*
H33C	−0.0118	0.4851	0.5636	0.108*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.1040 (17)	0.0554 (12)	0.0817 (14)	0.0161 (12)	0.0337 (13)	−0.0138 (10)
O9	0.0900 (15)	0.0484 (10)	0.0710 (12)	−0.0066 (10)	0.0377 (12)	0.0021 (9)
O6	0.1143 (18)	0.0433 (11)	0.0783 (13)	−0.0044 (11)	0.0459 (13)	0.0015 (10)
O5	0.0939 (16)	0.0582 (12)	0.0846 (14)	−0.0133 (11)	0.0358 (13)	0.0193 (10)
O4	0.1058 (17)	0.0433 (11)	0.0782 (14)	−0.0086 (11)	0.0237 (13)	−0.0016 (10)
C20	0.0519 (17)	0.0378 (14)	0.0535 (15)	−0.0028 (12)	0.0077 (14)	0.0068 (12)
O8	0.1176 (18)	0.0499 (11)	0.0879 (14)	0.0032 (11)	0.0607 (14)	−0.0037 (10)
C30	0.0686 (19)	0.0366 (14)	0.0607 (17)	−0.0083 (13)	0.0134 (15)	0.0082 (12)
C19	0.0555 (17)	0.0360 (13)	0.0539 (16)	−0.0018 (12)	0.0100 (14)	0.0021 (12)
C27	0.0500 (16)	0.0388 (14)	0.0516 (15)	−0.0042 (12)	0.0011 (13)	0.0074 (12)
C18	0.0529 (17)	0.0371 (14)	0.0519 (15)	0.0023 (12)	0.0045 (13)	0.0034 (12)
O3	0.150 (2)	0.0480 (12)	0.0827 (14)	0.0100 (13)	0.0566 (15)	0.0024 (10)
C6	0.077 (2)	0.0397 (15)	0.0696 (18)	−0.0008 (14)	0.0175 (17)	−0.0051 (13)
C11	0.0588 (18)	0.0501 (16)	0.0515 (16)	0.0066 (14)	0.0110 (14)	−0.0103 (13)
O7	0.1095 (17)	0.0499 (11)	0.0650 (12)	0.0041 (11)	0.0311 (12)	0.0018 (9)
C3	0.0570 (17)	0.0374 (14)	0.0558 (16)	0.0006 (13)	0.0085 (14)	−0.0057 (12)
C1	0.0617 (18)	0.0398 (14)	0.0560 (16)	0.0015 (13)	0.0078 (14)	−0.0039 (12)
C24	0.0606 (19)	0.0436 (15)	0.0570 (16)	−0.0027 (14)	0.0137 (15)	0.0091 (13)
C13	0.0695 (19)	0.0398 (14)	0.0605 (17)	−0.0007 (13)	0.0189 (15)	−0.0089 (13)
O2	0.1064 (17)	0.0411 (11)	0.0907 (14)	−0.0046 (11)	0.0302 (13)	−0.0003 (10)
O10	0.1030 (16)	0.0418 (10)	0.0872 (14)	0.0000 (11)	0.0438 (12)	0.0039 (10)
C32	0.0559 (17)	0.0410 (14)	0.0538 (16)	−0.0013 (13)	0.0092 (14)	0.0039 (12)
N2	0.0622 (16)	0.0460 (14)	0.0602 (15)	−0.0071 (12)	0.0045 (13)	0.0098 (12)
N1	0.0681 (17)	0.0458 (14)	0.0664 (15)	0.0041 (12)	0.0120 (14)	−0.0070 (12)
C4	0.069 (2)	0.0547 (17)	0.0596 (17)	0.0024 (15)	0.0206 (15)	−0.0069 (14)
C2	0.0637 (19)	0.0416 (15)	0.0548 (16)	0.0018 (13)	0.0142 (14)	−0.0013 (12)
C10	0.0548 (17)	0.0413 (14)	0.0525 (15)	0.0037 (13)	0.0042 (14)	−0.0061 (12)
C7	0.083 (2)	0.0443 (16)	0.0613 (18)	0.0037 (15)	0.0169 (16)	−0.0039 (14)
C14	0.0647 (19)	0.0504 (16)	0.0595 (17)	−0.0002 (14)	0.0221 (15)	−0.0120 (13)
C26	0.0600 (18)	0.0418 (15)	0.0570 (16)	−0.0044 (13)	0.0080 (15)	0.0030 (12)
C31	0.0577 (18)	0.0456 (15)	0.0520 (16)	−0.0064 (13)	0.0112 (14)	0.0067 (13)
C9	0.070 (2)	0.0447 (16)	0.0577 (17)	0.0073 (14)	0.0115 (15)	−0.0039 (13)
C8	0.087 (2)	0.0401 (15)	0.0636 (18)	0.0047 (15)	0.0186 (17)	−0.0049 (13)
C15	0.0674 (19)	0.0424 (14)	0.0564 (16)	0.0019 (14)	0.0139 (15)	−0.0036 (12)
C12	0.0619 (18)	0.0484 (16)	0.0474 (15)	−0.0024 (14)	0.0148 (14)	−0.0007 (12)
C23	0.068 (2)	0.0389 (14)	0.0679 (18)	−0.0010 (14)	0.0135 (16)	0.0016 (14)
C21	0.0643 (19)	0.0544 (16)	0.0557 (17)	0.0007 (15)	0.0177 (15)	0.0053 (14)
C22	0.078 (2)	0.0491 (17)	0.0651 (18)	0.0027 (15)	0.0198 (17)	−0.0042 (14)
C29	0.0670 (19)	0.0449 (15)	0.0593 (17)	0.0004 (14)	0.0148 (15)	0.0037 (13)
C25	0.0605 (18)	0.0402 (14)	0.0666 (18)	0.0006 (13)	0.0098 (15)	0.0071 (13)
C28	0.0635 (19)	0.0427 (15)	0.0575 (16)	−0.0048 (14)	0.0150 (14)	0.0087 (13)
C5	0.089 (2)	0.0480 (17)	0.0722 (19)	−0.0045 (16)	0.0301 (18)	−0.0013 (14)
C34	0.081 (2)	0.0608 (18)	0.0684 (18)	−0.0016 (16)	0.0267 (17)	−0.0063 (15)
C16	0.146 (3)	0.0363 (16)	0.085 (2)	0.0088 (18)	0.029 (2)	0.0004 (15)
C17	0.103 (3)	0.0638 (19)	0.080 (2)	−0.0004 (18)	0.0452 (19)	0.0055 (16)
C33	0.090 (2)	0.0385 (15)	0.089 (2)	−0.0007 (15)	0.0210 (18)	0.0053 (14)

Geometric parameters (Å, º)

O1—N1	1.229 (2)	O2—N1	1.219 (2)
O9—C31	1.370 (3)	O10—C29	1.382 (3)
O9—C34	1.420 (3)	O10—C33	1.428 (3)
O6—C24	1.220 (3)	C32—C31	1.385 (3)
O5—N2	1.228 (2)	C32—H32	0.9300
O4—N2	1.223 (2)	C4—C5	1.383 (3)
C20—C19	1.372 (3)	C4—H4	0.9300
C20—C21	1.377 (3)	C2—H2	0.9300
C20—N2	1.475 (3)	C10—C15	1.395 (3)
O8—C14	1.369 (3)	C10—C9	1.468 (3)
O8—C17	1.414 (3)	C7—C8	1.469 (3)
C30—C29	1.376 (3)	C14—C15	1.381 (3)
C30—C31	1.384 (3)	C26—C25	1.321 (3)
C30—H30	0.9300	C26—H26	0.9300
C19—C18	1.396 (3)	C9—C8	1.316 (3)
C19—H19	0.9300	C9—H9	0.9300
C27—C28	1.383 (3)	C8—H8	0.9300
C27—C32	1.400 (3)	C15—H15	0.9300
C27—C26	1.472 (3)	C23—C22	1.379 (3)
C18—C23	1.388 (3)	C23—H23	0.9300
C18—C24	1.497 (3)	C21—C22	1.378 (3)
O3—C7	1.220 (3)	C21—H21	0.9300
C6—C5	1.374 (3)	C22—H22	0.9300
C6—C1	1.392 (3)	C29—C28	1.389 (3)
C6—H6	0.9300	C25—H25	0.9300
C11—C10	1.383 (3)	C28—H28	0.9300
C11—C12	1.386 (3)	C5—H5	0.9300
C11—H11	0.9300	C34—H34A	0.9600
O7—C12	1.374 (3)	C34—H34B	0.9600
O7—C16	1.423 (3)	C34—H34C	0.9600
C3—C2	1.367 (3)	C16—H16A	0.9600
C3—C4	1.369 (3)	C16—H16B	0.9600
C3—N1	1.477 (3)	C16—H16C	0.9600
C1—C2	1.395 (3)	C17—H17A	0.9600
C1—C7	1.507 (3)	C17—H17B	0.9600
C24—C25	1.475 (3)	C17—H17C	0.9600
C13—C12	1.373 (3)	C33—H33A	0.9600
C13—C14	1.389 (3)	C33—H33B	0.9600
C13—H13	0.9300	C33—H33C	0.9600
C31—O9—C34	118.13 (19)	C25—C26—H26	116.6
C19—C20—C21	122.4 (2)	C27—C26—H26	116.6
C19—C20—N2	118.6 (2)	O9—C31—C30	114.8 (2)
C21—C20—N2	119.0 (2)	O9—C31—C32	124.6 (2)
C14—O8—C17	118.6 (2)	C30—C31—C32	120.6 (2)
C29—C30—C31	119.5 (2)	C8—C9—C10	127.2 (2)
C29—C30—H30	120.3	C8—C9—H9	116.4
C31—C30—H30	120.3	C10—C9—H9	116.4
C20—C19—C18	119.7 (2)	C9—C8—C7	122.5 (3)
C20—C19—H19	120.2	C9—C8—H8	118.8
C18—C19—H19	120.2	C7—C8—H8	118.8
C28—C27—C32	120.1 (2)	C14—C15—C10	119.3 (2)
C28—C27—C26	121.7 (2)	C14—C15—H15	120.4
C32—C27—C26	118.2 (2)	C10—C15—H15	120.4
C23—C18—C19	118.0 (2)	C13—C12—O7	124.0 (2)
C23—C18—C24	124.0 (2)	C13—C12—C11	120.6 (2)
C19—C18—C24	118.0 (2)	O7—C12—C11	115.4 (2)
C5—C6—C1	120.8 (2)	C22—C23—C18	121.4 (2)
C5—C6—H6	119.6	C22—C23—H23	119.3
C1—C6—H6	119.6	C18—C23—H23	119.3
C10—C11—C12	120.0 (2)	C20—C21—C22	118.2 (2)
C10—C11—H11	120.0	C20—C21—H21	120.9
C12—C11—H11	120.0	C22—C21—H21	120.9
C12—O7—C16	118.3 (2)	C21—C22—C23	120.4 (2)
C2—C3—C4	123.0 (2)	C21—C22—H22	119.8
C2—C3—N1	118.8 (2)	C23—C22—H22	119.8
C4—C3—N1	118.2 (2)	C30—C29—O10	124.0 (2)
C6—C1—C2	118.6 (2)	C30—C29—C28	121.0 (2)
C6—C1—C7	123.5 (2)	O10—C29—C28	115.0 (2)
C2—C1—C7	117.9 (2)	C26—C25—C24	121.7 (2)
O6—C24—C25	121.1 (2)	C26—C25—H25	119.2
O6—C24—C18	119.5 (2)	C24—C25—H25	119.2
C25—C24—C18	119.4 (2)	C27—C28—C29	119.4 (2)
C12—C13—C14	119.3 (2)	C27—C28—H28	120.3
C12—C13—H13	120.4	C29—C28—H28	120.3
C14—C13—H13	120.4	C6—C5—C4	120.6 (2)
C29—O10—C33	117.2 (2)	C6—C5—H5	119.7
C31—C32—C27	119.3 (2)	C4—C5—H5	119.7
C31—C32—H32	120.3	O9—C34—H34A	109.5
C27—C32—H32	120.3	O9—C34—H34B	109.5
O4—N2—O5	123.7 (2)	H34A—C34—H34B	109.5
O4—N2—C20	118.7 (2)	O9—C34—H34C	109.5
O5—N2—C20	117.6 (2)	H34A—C34—H34C	109.5
O2—N1—O1	123.9 (2)	H34B—C34—H34C	109.5
O2—N1—C3	118.5 (2)	O7—C16—H16A	109.5
O1—N1—C3	117.7 (2)	O7—C16—H16B	109.5
C3—C4—C5	118.0 (2)	H16A—C16—H16B	109.5
C3—C4—H4	121.0	O7—C16—H16C	109.5
C5—C4—H4	121.0	H16A—C16—H16C	109.5
C3—C2—C1	119.0 (2)	H16B—C16—H16C	109.5
C3—C2—H2	120.5	O8—C17—H17A	109.5
C1—C2—H2	120.5	O8—C17—H17B	109.5
C11—C10—C15	119.9 (2)	H17A—C17—H17B	109.5
C11—C10—C9	121.8 (2)	O8—C17—H17C	109.5
C15—C10—C9	118.3 (2)	H17A—C17—H17C	109.5
O3—C7—C8	121.6 (2)	H17B—C17—H17C	109.5
O3—C7—C1	120.0 (2)	O10—C33—H33A	109.5
C8—C7—C1	118.4 (2)	O10—C33—H33B	109.5
O8—C14—C15	124.4 (2)	H33A—C33—H33B	109.5
O8—C14—C13	114.6 (2)	O10—C33—H33C	109.5
C15—C14—C13	121.0 (2)	H33A—C33—H33C	109.5
C25—C26—C27	126.9 (2)	H33B—C33—H33C	109.5
C21—C20—C19—C18	−0.3 (4)	C34—O9—C31—C32	−6.3 (4)
N2—C20—C19—C18	178.1 (2)	C29—C30—C31—O9	−179.9 (2)
C20—C19—C18—C23	0.4 (4)	C29—C30—C31—C32	0.9 (4)
C20—C19—C18—C24	−178.8 (2)	C27—C32—C31—O9	−179.1 (2)
C5—C6—C1—C2	−0.6 (4)	C27—C32—C31—C30	0.0 (4)
C5—C6—C1—C7	178.6 (3)	C11—C10—C9—C8	0.6 (4)
C23—C18—C24—O6	−171.0 (3)	C15—C10—C9—C8	−178.4 (3)
C19—C18—C24—O6	8.1 (4)	C10—C9—C8—C7	179.1 (3)
C23—C18—C24—C25	7.9 (4)	O3—C7—C8—C9	0.0 (5)
C19—C18—C24—C25	−173.0 (2)	C1—C7—C8—C9	−178.5 (3)
C28—C27—C32—C31	−1.0 (4)	O8—C14—C15—C10	−179.9 (2)
C26—C27—C32—C31	179.8 (2)	C13—C14—C15—C10	−0.3 (4)
C19—C20—N2—O4	−2.9 (4)	C11—C10—C15—C14	−0.1 (4)
C21—C20—N2—O4	175.6 (2)	C9—C10—C15—C14	179.0 (2)
C19—C20—N2—O5	177.3 (2)	C14—C13—C12—O7	−179.7 (3)
C21—C20—N2—O5	−4.3 (4)	C14—C13—C12—C11	0.1 (4)
C2—C3—N1—O2	−8.6 (4)	C16—O7—C12—C13	1.2 (4)
C4—C3—N1—O2	172.1 (2)	C16—O7—C12—C11	−178.6 (2)
C2—C3—N1—O1	171.6 (2)	C10—C11—C12—C13	−0.4 (4)
C4—C3—N1—O1	−7.7 (4)	C10—C11—C12—O7	179.4 (2)
C2—C3—C4—C5	−0.3 (4)	C19—C18—C23—C22	−0.2 (4)
N1—C3—C4—C5	179.0 (2)	C24—C18—C23—C22	178.9 (2)
C4—C3—C2—C1	0.1 (4)	C19—C20—C21—C22	0.1 (4)
N1—C3—C2—C1	−179.1 (2)	N2—C20—C21—C22	−178.3 (2)
C6—C1—C2—C3	0.3 (4)	C20—C21—C22—C23	0.1 (4)
C7—C1—C2—C3	−179.0 (2)	C18—C23—C22—C21	−0.1 (4)
C12—C11—C10—C15	0.4 (4)	C31—C30—C29—O10	179.0 (2)
C12—C11—C10—C9	−178.6 (2)	C31—C30—C29—C28	−0.7 (4)
C6—C1—C7—O3	174.1 (3)	C33—O10—C29—C30	−1.5 (4)
C2—C1—C7—O3	−6.6 (4)	C33—O10—C29—C28	178.2 (2)
C6—C1—C7—C8	−7.4 (4)	C27—C26—C25—C24	179.4 (2)
C2—C1—C7—C8	171.9 (2)	O6—C24—C25—C26	4.4 (4)
C17—O8—C14—C15	1.6 (4)	C18—C24—C25—C26	−174.5 (2)
C17—O8—C14—C13	−178.0 (3)	C32—C27—C28—C29	1.2 (4)
C12—C13—C14—O8	179.9 (2)	C26—C27—C28—C29	−179.7 (2)
C12—C13—C14—C15	0.3 (4)	C30—C29—C28—C27	−0.3 (4)
C28—C27—C26—C25	1.2 (4)	O10—C29—C28—C27	180.0 (2)
C32—C27—C26—C25	−179.7 (3)	C1—C6—C5—C4	0.5 (5)
C34—O9—C31—C30	174.5 (2)	C3—C4—C5—C6	−0.1 (4)