N,N′-Bis(2,5-dimethoxy­phen­yl)oxamide

The title compound, C₁₈H₂₀N₂O₆, has two independent mol­ecules in the asymmetric unit. Intra­molecular N—H...O and C—H...O hydrogen bonds make the mol­ecules essentially planar. The crystal packing is stabilized by C—H...O and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.064
• wR factor = 0.109
• Data-to-parameter ratio = 7.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.70
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.81 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.05 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C7     -   C8     ...       1.55 Ang.

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           26.12
           From the CIF: _reflns_number_total               3611
           Count of symmetry unique reflns         3652
           Completeness (_total/calc)             98.88%
           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
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   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 (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

N,N'-Bis(2,5-dimethoxyphenyl)oxamide

Crystal data

C18H20N2O6	F(000) = 760
Mr = 360.36	Dx = 1.350 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 618 reflections
a = 6.597 (3) Å	θ = 2.7–18.9°
b = 17.427 (7) Å	µ = 0.10 mm^−1
c = 15.433 (6) Å	T = 293 K
β = 91.496 (9)°	Needle, colourless
V = 1773.7 (13) Å^3	0.46 × 0.06 × 0.05 mm
Z = 4

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	3611 independent reflections
Radiation source: fine-focus sealed tube	1861 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.089
Detector resolution: 8.33 pixels mm^-1	θmax = 26.1°, θmin = 1.3°
ω scans	h = −8→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −21→21
Tmin = 0.954, Tmax = 0.995	l = −19→9
10019 measured reflections

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.028P)^2] where P = (Fo^2 + 2Fc^2)/3
3611 reflections	(Δ/σ)max = 0.001
469 parameters	Δρmax = 0.19 e Å^−3
1 restraint	Δρmin = −0.19 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.

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	0.0963 (6)	0.5206 (2)	0.3587 (3)	0.0499 (13)
O2	−0.0475 (6)	0.7127 (3)	0.3808 (3)	0.0480 (13)
O3	0.7043 (6)	0.4066 (3)	0.4727 (3)	0.0613 (14)
O4	0.4993 (6)	0.7093 (2)	0.5196 (3)	0.0479 (13)
O5	−0.4385 (6)	0.5239 (3)	0.2147 (3)	0.0522 (13)
O6	−0.6562 (7)	0.8249 (3)	0.2676 (3)	0.0607 (14)
N1	0.2550 (7)	0.6197 (3)	0.4299 (3)	0.0383 (15)
H1A	0.2383	0.6675	0.4412	0.046*
N2	−0.2047 (7)	0.6132 (3)	0.3089 (3)	0.0358 (14)
H2A	−0.1872	0.5654	0.2975	0.043*
C1	0.4891 (10)	0.5103 (4)	0.4519 (4)	0.0420 (18)
H1	0.4076	0.4786	0.4172	0.050*
C2	0.6620 (11)	0.4825 (4)	0.4898 (5)	0.046 (2)
C3	0.7906 (10)	0.5291 (4)	0.5394 (5)	0.051 (2)
H3	0.9087	0.5093	0.5649	0.061*
C4	0.7396 (9)	0.6061 (4)	0.5503 (4)	0.0422 (19)
H4	0.8248	0.6381	0.5828	0.051*
C5	0.5655 (10)	0.6348 (4)	0.5134 (4)	0.0410 (18)
C6	0.4349 (9)	0.5859 (4)	0.4651 (4)	0.0316 (16)
C7	0.1100 (8)	0.5873 (4)	0.3820 (4)	0.0316 (16)
C8	−0.0567 (10)	0.6464 (4)	0.3568 (4)	0.0391 (17)
C9	−0.3855 (9)	0.6459 (4)	0.2745 (4)	0.0356 (17)
C10	−0.5117 (9)	0.5978 (4)	0.2246 (4)	0.0341 (16)
C11	−0.6871 (10)	0.6262 (4)	0.1893 (4)	0.045 (2)
H11	−0.7714	0.5940	0.1565	0.053*
C12	−0.7430 (10)	0.7022 (4)	0.2014 (4)	0.0446 (19)
H12	−0.8623	0.7212	0.1762	0.054*
C13	−0.6196 (10)	0.7486 (4)	0.2511 (5)	0.0408 (18)
C14	−0.4390 (8)	0.7218 (4)	0.2882 (4)	0.0378 (18)
H14	−0.3559	0.7541	0.3214	0.045*
C15	0.8739 (12)	0.3721 (4)	0.5163 (5)	0.083 (3)
H15A	0.8737	0.3179	0.5052	0.125*
H15B	0.8657	0.3809	0.5775	0.125*
H15C	0.9968	0.3943	0.4956	0.125*
C16	0.6344 (11)	0.7639 (4)	0.5571 (6)	0.073 (3)
H16A	0.5730	0.8138	0.5547	0.109*
H16B	0.7579	0.7645	0.5255	0.109*
H16C	0.6638	0.7503	0.6163	0.109*
C17	−0.5735 (12)	0.4696 (4)	0.1749 (6)	0.087 (3)
H17A	−0.5130	0.4195	0.1770	0.131*
H17B	−0.5997	0.4839	0.1156	0.131*
H17C	−0.6987	0.4689	0.2052	0.131*
C18	−0.8358 (10)	0.8574 (4)	0.2288 (5)	0.081 (3)
H18A	−0.8415	0.9111	0.2420	0.122*
H18B	−0.9528	0.8322	0.2512	0.122*
H18C	−0.8337	0.8506	0.1671	0.122*
O7	0.4509 (6)	0.0885 (3)	0.1340 (3)	0.0485 (13)
O8	0.5941 (6)	0.2808 (2)	0.1082 (3)	0.0472 (13)
O9	−0.1468 (7)	0.0002 (2)	0.2712 (3)	0.0568 (14)
O10	0.0723 (7)	0.3042 (2)	0.2465 (3)	0.0536 (13)
O11	0.9768 (6)	0.0643 (2)	−0.0009 (3)	0.0495 (13)
O12	1.1908 (7)	0.3674 (3)	−0.0315 (3)	0.0675 (16)
N3	0.3008 (7)	0.1994 (3)	0.1788 (3)	0.0376 (14)
H3A	0.3181	0.2483	0.1782	0.045*
N4	0.7457 (7)	0.1697 (3)	0.0631 (3)	0.0383 (14)
H4A	0.7269	0.1208	0.0631	0.046*
C19	0.0684 (9)	0.0978 (4)	0.2276 (4)	0.0400 (18)
H19	0.1481	0.0599	0.2032	0.048*
C20	−0.1059 (9)	0.0778 (4)	0.2706 (5)	0.0397 (18)
C21	−0.2227 (10)	0.1345 (4)	0.3064 (4)	0.0431 (18)
H21	−0.3405	0.1218	0.3349	0.052*
C22	−0.1643 (9)	0.2100 (4)	0.3000 (5)	0.0439 (19)
H22	−0.2427	0.2479	0.3253	0.053*
C23	0.0061 (9)	0.2307 (4)	0.2573 (4)	0.0399 (18)
C24	0.1232 (9)	0.1735 (4)	0.2213 (4)	0.0331 (16)
C25	0.4431 (9)	0.1587 (4)	0.1401 (4)	0.0357 (18)
C26	0.6028 (9)	0.2107 (4)	0.1025 (5)	0.0392 (18)
C27	0.9218 (8)	0.1945 (4)	0.0217 (4)	0.0345 (17)
C28	1.0439 (10)	0.1386 (4)	−0.0120 (4)	0.0361 (17)
C29	1.2167 (10)	0.1579 (4)	−0.0537 (4)	0.048 (2)
H29	1.2984	0.1196	−0.0761	0.057*
C30	1.2709 (10)	0.2350 (4)	−0.0627 (5)	0.0438 (19)
H30	1.3866	0.2483	−0.0924	0.053*
C31	1.1550 (10)	0.2897 (4)	−0.0282 (5)	0.0458 (19)
C32	0.9742 (10)	0.2716 (4)	0.0137 (4)	0.0431 (18)
H32	0.8919	0.3100	0.0354	0.052*
C33	−0.3286 (11)	−0.0235 (4)	0.3114 (5)	0.070 (3)
H33A	−0.3340	−0.0786	0.3130	0.105*
H33B	−0.4436	−0.0043	0.2788	0.105*
H33C	−0.3305	−0.0037	0.3694	0.105*
C34	−0.0659 (11)	0.3657 (4)	0.2633 (6)	0.079 (3)
H34A	0.0013	0.4140	0.2551	0.119*
H34B	−0.1104	0.3622	0.3219	0.119*
H34C	−0.1809	0.3622	0.2241	0.119*
C35	1.1113 (11)	0.0038 (4)	−0.0232 (6)	0.076 (3)
H35A	1.0502	−0.0447	−0.0103	0.114*
H35B	1.2362	0.0090	0.0096	0.114*
H35C	1.1382	0.0064	−0.0840	0.114*
C36	1.3657 (12)	0.3916 (5)	−0.0769 (5)	0.080 (3)
H36A	1.3718	0.4466	−0.0775	0.120*
H36B	1.3573	0.3728	−0.1354	0.120*
H36C	1.4855	0.3715	−0.0485	0.120*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.039 (3)	0.043 (3)	0.068 (4)	0.001 (2)	−0.014 (3)	−0.013 (3)
O2	0.041 (3)	0.048 (3)	0.054 (4)	0.006 (2)	−0.008 (2)	−0.010 (3)
O3	0.054 (3)	0.053 (3)	0.076 (4)	0.013 (3)	−0.018 (3)	0.009 (3)
O4	0.042 (3)	0.046 (3)	0.056 (3)	0.000 (2)	−0.007 (2)	−0.013 (3)
O5	0.040 (3)	0.049 (3)	0.067 (4)	−0.003 (2)	−0.001 (3)	−0.017 (3)
O6	0.061 (3)	0.045 (3)	0.075 (4)	0.015 (3)	−0.008 (3)	0.001 (3)
N1	0.033 (3)	0.037 (3)	0.045 (4)	0.007 (3)	−0.006 (3)	−0.007 (3)
N2	0.033 (3)	0.038 (3)	0.037 (4)	−0.001 (2)	−0.003 (3)	−0.002 (3)
C1	0.041 (4)	0.040 (4)	0.044 (5)	−0.005 (3)	−0.004 (4)	0.008 (4)
C2	0.058 (5)	0.036 (4)	0.046 (5)	−0.002 (4)	0.001 (4)	0.009 (4)
C3	0.042 (4)	0.055 (5)	0.055 (6)	0.001 (4)	−0.015 (4)	0.000 (4)
C4	0.030 (4)	0.057 (5)	0.039 (5)	−0.003 (3)	−0.007 (4)	−0.002 (4)
C5	0.047 (4)	0.047 (5)	0.029 (4)	−0.002 (4)	−0.004 (4)	−0.020 (4)
C6	0.037 (4)	0.038 (4)	0.019 (4)	0.000 (3)	0.000 (3)	0.008 (3)
C7	0.026 (4)	0.032 (4)	0.038 (4)	0.002 (3)	0.000 (3)	0.000 (4)
C8	0.038 (4)	0.050 (5)	0.029 (4)	−0.006 (4)	0.001 (3)	−0.003 (4)
C9	0.027 (4)	0.045 (4)	0.035 (5)	0.006 (3)	0.003 (3)	0.002 (4)
C10	0.026 (4)	0.047 (4)	0.029 (4)	0.004 (3)	0.004 (3)	0.001 (4)
C11	0.046 (5)	0.052 (5)	0.035 (5)	−0.004 (4)	−0.004 (4)	0.004 (4)
C12	0.034 (4)	0.061 (5)	0.038 (5)	0.017 (4)	0.000 (4)	0.009 (4)
C13	0.040 (4)	0.045 (5)	0.037 (5)	0.005 (4)	0.002 (4)	−0.004 (4)
C14	0.026 (3)	0.045 (4)	0.042 (5)	−0.004 (3)	−0.003 (3)	0.001 (4)
C15	0.105 (7)	0.060 (6)	0.083 (7)	0.040 (5)	−0.030 (6)	0.004 (5)
C16	0.049 (5)	0.056 (5)	0.113 (8)	−0.003 (4)	−0.013 (5)	−0.029 (5)
C17	0.074 (6)	0.046 (5)	0.141 (9)	−0.007 (5)	−0.018 (6)	−0.022 (6)
C18	0.060 (5)	0.081 (6)	0.102 (8)	0.032 (5)	−0.014 (5)	0.007 (6)
O7	0.040 (3)	0.040 (3)	0.066 (4)	0.003 (2)	0.012 (3)	−0.001 (3)
O8	0.038 (3)	0.046 (3)	0.058 (4)	−0.003 (2)	0.007 (2)	−0.002 (3)
O9	0.053 (3)	0.046 (3)	0.072 (4)	−0.003 (3)	0.022 (3)	0.009 (3)
O10	0.051 (3)	0.040 (3)	0.071 (4)	0.000 (2)	0.013 (3)	−0.006 (3)
O11	0.038 (3)	0.040 (3)	0.071 (4)	0.000 (2)	0.015 (3)	−0.008 (3)
O12	0.064 (4)	0.046 (3)	0.093 (4)	−0.003 (3)	0.029 (3)	0.013 (3)
N3	0.028 (3)	0.040 (3)	0.045 (4)	0.007 (3)	0.003 (3)	−0.002 (3)
N4	0.034 (3)	0.034 (3)	0.047 (4)	−0.003 (3)	0.010 (3)	0.000 (3)
C19	0.035 (4)	0.040 (4)	0.045 (5)	0.004 (3)	0.001 (4)	−0.004 (4)
C20	0.033 (4)	0.045 (5)	0.042 (5)	−0.003 (4)	0.008 (4)	0.008 (4)
C21	0.037 (4)	0.058 (5)	0.034 (5)	0.002 (4)	0.005 (3)	0.004 (4)
C22	0.038 (4)	0.044 (5)	0.049 (5)	0.001 (4)	0.005 (4)	−0.009 (4)
C23	0.031 (4)	0.047 (5)	0.042 (5)	−0.005 (3)	0.006 (3)	0.010 (4)
C24	0.030 (4)	0.046 (4)	0.023 (4)	0.006 (3)	0.009 (3)	−0.004 (3)
C25	0.032 (4)	0.040 (5)	0.034 (5)	0.001 (3)	0.002 (3)	0.006 (4)
C26	0.031 (4)	0.042 (5)	0.044 (5)	0.000 (4)	−0.003 (3)	−0.005 (4)
C27	0.022 (3)	0.050 (5)	0.032 (4)	0.006 (3)	−0.003 (3)	−0.001 (4)
C28	0.033 (4)	0.047 (5)	0.029 (4)	0.006 (4)	0.001 (3)	0.000 (4)
C29	0.048 (5)	0.051 (5)	0.044 (5)	0.004 (4)	0.010 (4)	−0.005 (4)
C30	0.035 (4)	0.052 (5)	0.045 (5)	−0.004 (4)	0.016 (4)	−0.005 (4)
C31	0.048 (5)	0.042 (5)	0.048 (5)	−0.012 (4)	0.009 (4)	−0.003 (4)
C32	0.037 (4)	0.048 (5)	0.045 (5)	0.005 (3)	0.010 (4)	0.003 (4)
C33	0.069 (6)	0.061 (5)	0.082 (7)	−0.022 (4)	0.022 (5)	−0.003 (5)
C34	0.068 (6)	0.053 (5)	0.117 (8)	0.006 (5)	0.028 (6)	−0.023 (6)
C35	0.075 (6)	0.035 (5)	0.119 (8)	0.001 (4)	0.028 (6)	−0.026 (5)
C36	0.075 (6)	0.079 (6)	0.088 (7)	−0.031 (5)	0.037 (5)	0.013 (5)

Geometric parameters (Å, º)

O1—C7	1.219 (7)	O7—C25	1.227 (7)
O2—C8	1.213 (7)	O8—C26	1.227 (7)
O3—C2	1.379 (7)	O9—C20	1.379 (7)
O3—C15	1.423 (7)	O9—C33	1.426 (7)
O4—C5	1.374 (7)	O10—C23	1.365 (7)
O4—C16	1.417 (7)	O10—C34	1.435 (7)
O5—C10	1.385 (7)	O11—C28	1.382 (7)
O5—C17	1.427 (7)	O11—C35	1.426 (7)
O6—C13	1.376 (7)	O12—C31	1.375 (7)
O6—C18	1.431 (7)	O12—C36	1.429 (8)
N1—C7	1.320 (7)	N3—C25	1.330 (7)
N1—C6	1.420 (7)	N3—C24	1.430 (8)
N1—H1A	0.86	N3—H3A	0.86
N2—C8	1.341 (7)	N4—C26	1.341 (8)
N2—C9	1.412 (7)	N4—C27	1.408 (7)
N2—H2A	0.86	N4—H4A	0.86
C1—C2	1.358 (8)	C19—C24	1.373 (8)
C1—C6	1.383 (8)	C19—C20	1.386 (8)
C1—H1	0.93	C19—H19	0.93
C2—C3	1.390 (8)	C20—C21	1.378 (9)
C3—C4	1.395 (9)	C21—C22	1.375 (8)
C3—H3	0.93	C21—H21	0.93
C4—C5	1.363 (9)	C22—C23	1.366 (8)
C4—H4	0.93	C22—H22	0.93
C5—C6	1.411 (8)	C23—C24	1.387 (8)
C7—C8	1.549 (7)	C25—C26	1.517 (8)
C9—C14	1.386 (8)	C27—C28	1.375 (8)
C9—C10	1.400 (8)	C27—C32	1.393 (8)
C10—C11	1.359 (8)	C28—C29	1.365 (8)
C11—C12	1.389 (8)	C29—C30	1.399 (8)
C11—H11	0.93	C29—H29	0.93
C12—C13	1.369 (8)	C30—C31	1.342 (8)
C12—H12	0.93	C30—H30	0.93
C13—C14	1.389 (8)	C31—C32	1.407 (9)
C14—H14	0.93	C32—H32	0.93
C15—H15A	0.96	C33—H33A	0.96
C15—H15B	0.96	C33—H33B	0.96
C15—H15C	0.96	C33—H33C	0.96
C16—H16A	0.96	C34—H34A	0.96
C16—H16B	0.96	C34—H34B	0.96
C16—H16C	0.96	C34—H34C	0.96
C17—H17A	0.96	C35—H35A	0.96
C17—H17B	0.96	C35—H35B	0.96
C17—H17C	0.96	C35—H35C	0.96
C18—H18A	0.96	C36—H36A	0.96
C18—H18B	0.96	C36—H36B	0.96
C18—H18C	0.96	C36—H36C	0.96
C2—O3—C15	118.4 (6)	C20—O9—C33	117.0 (5)
C5—O4—C16	117.7 (5)	C23—O10—C34	118.2 (5)
C10—O5—C17	116.6 (5)	C28—O11—C35	117.4 (5)
C13—O6—C18	116.9 (6)	C31—O12—C36	116.7 (6)
C7—N1—C6	128.6 (6)	C25—N3—C24	129.3 (5)
C7—N1—H1A	115.7	C25—N3—H3A	115.3
C6—N1—H1A	115.7	C24—N3—H3A	115.3
C8—N2—C9	128.9 (6)	C26—N4—C27	129.8 (6)
C8—N2—H2A	115.5	C26—N4—H4A	115.1
C9—N2—H2A	115.5	C27—N4—H4A	115.1
C2—C1—C6	119.6 (7)	C24—C19—C20	120.0 (6)
C2—C1—H1	120.2	C24—C19—H19	120.0
C6—C1—H1	120.2	C20—C19—H19	120.0
C1—C2—O3	115.6 (6)	O9—C20—C21	126.1 (6)
C1—C2—C3	121.5 (6)	O9—C20—C19	114.5 (6)
O3—C2—C3	122.8 (6)	C21—C20—C19	119.4 (6)
C2—C3—C4	118.9 (6)	C22—C21—C20	119.8 (7)
C2—C3—H3	120.6	C22—C21—H21	120.1
C4—C3—H3	120.6	C20—C21—H21	120.1
C5—C4—C3	120.4 (7)	C23—C22—C21	121.5 (7)
C5—C4—H4	119.8	C23—C22—H22	119.2
C3—C4—H4	119.8	C21—C22—H22	119.2
C4—C5—O4	125.7 (6)	C22—C23—O10	125.2 (6)
C4—C5—C6	119.7 (6)	C22—C23—C24	118.6 (6)
O4—C5—C6	114.6 (6)	O10—C23—C24	116.2 (6)
C1—C6—C5	119.8 (6)	C19—C24—C23	120.8 (6)
C1—C6—N1	123.7 (6)	C19—C24—N3	123.8 (6)
C5—C6—N1	116.5 (6)	C23—C24—N3	115.4 (6)
O1—C7—N1	128.2 (6)	O7—C25—N3	126.6 (6)
O1—C7—C8	120.9 (5)	O7—C25—C26	122.4 (6)
N1—C7—C8	110.8 (5)	N3—C25—C26	111.0 (5)
O2—C8—N2	127.5 (6)	O8—C26—N4	126.8 (6)
O2—C8—C7	121.8 (6)	O8—C26—C25	122.2 (6)
N2—C8—C7	110.7 (6)	N4—C26—C25	111.0 (5)
C14—C9—C10	120.4 (6)	C28—C27—C32	120.0 (6)
C14—C9—N2	123.0 (6)	C28—C27—N4	116.9 (6)
C10—C9—N2	116.7 (6)	C32—C27—N4	123.1 (6)
C11—C10—O5	126.2 (6)	C29—C28—C27	120.6 (7)
C11—C10—C9	119.3 (6)	C29—C28—O11	124.3 (6)
O5—C10—C9	114.5 (5)	C27—C28—O11	115.1 (6)
C10—C11—C12	121.3 (7)	C28—C29—C30	120.1 (7)
C10—C11—H11	119.3	C28—C29—H29	119.9
C12—C11—H11	119.3	C30—C29—H29	119.9
C13—C12—C11	118.9 (6)	C31—C30—C29	119.6 (7)
C13—C12—H12	120.6	C31—C30—H30	120.2
C11—C12—H12	120.6	C29—C30—H30	120.2
C12—C13—O6	124.8 (6)	C30—C31—O12	125.8 (6)
C12—C13—C14	121.6 (6)	C30—C31—C32	121.4 (6)
O6—C13—C14	113.7 (6)	O12—C31—C32	112.8 (6)
C9—C14—C13	118.5 (6)	C27—C32—C31	118.2 (6)
C9—C14—H14	120.7	C27—C32—H32	120.9
C13—C14—H14	120.7	C31—C32—H32	120.9
O3—C15—H15A	109.5	O9—C33—H33A	109.5
O3—C15—H15B	109.5	O9—C33—H33B	109.5
H15A—C15—H15B	109.5	H33A—C33—H33B	109.5
O3—C15—H15C	109.5	O9—C33—H33C	109.5
H15A—C15—H15C	109.5	H33A—C33—H33C	109.5
H15B—C15—H15C	109.5	H33B—C33—H33C	109.5
O4—C16—H16A	109.5	O10—C34—H34A	109.5
O4—C16—H16B	109.5	O10—C34—H34B	109.5
H16A—C16—H16B	109.5	H34A—C34—H34B	109.5
O4—C16—H16C	109.5	O10—C34—H34C	109.5
H16A—C16—H16C	109.5	H34A—C34—H34C	109.5
H16B—C16—H16C	109.5	H34B—C34—H34C	109.5
O5—C17—H17A	109.5	O11—C35—H35A	109.5
O5—C17—H17B	109.5	O11—C35—H35B	109.5
H17A—C17—H17B	109.5	H35A—C35—H35B	109.5
O5—C17—H17C	109.5	O11—C35—H35C	109.5
H17A—C17—H17C	109.5	H35A—C35—H35C	109.5
H17B—C17—H17C	109.5	H35B—C35—H35C	109.5
O6—C18—H18A	109.5	O12—C36—H36A	109.5
O6—C18—H18B	109.5	O12—C36—H36B	109.5
H18A—C18—H18B	109.5	H36A—C36—H36B	109.5
O6—C18—H18C	109.5	O12—C36—H36C	109.5
H18A—C18—H18C	109.5	H36A—C36—H36C	109.5
H18B—C18—H18C	109.5	H36B—C36—H36C	109.5
C6—C1—C2—O3	−179.7 (6)	C33—O9—C20—C21	1.2 (10)
C6—C1—C2—C3	−2.4 (11)	C33—O9—C20—C19	−177.5 (6)
C15—O3—C2—C1	−174.8 (7)	C24—C19—C20—O9	178.9 (6)
C15—O3—C2—C3	7.9 (10)	C24—C19—C20—C21	0.0 (10)
C1—C2—C3—C4	0.2 (11)	O9—C20—C21—C22	−179.3 (7)
O3—C2—C3—C4	177.3 (6)	C19—C20—C21—C22	−0.6 (10)
C2—C3—C4—C5	0.6 (11)	C20—C21—C22—C23	1.2 (11)
C3—C4—C5—O4	179.9 (7)	C21—C22—C23—O10	178.6 (6)
C3—C4—C5—C6	0.9 (11)	C21—C22—C23—C24	−1.1 (10)
C16—O4—C5—C4	9.2 (11)	C34—O10—C23—C22	−14.7 (10)
C16—O4—C5—C6	−171.8 (6)	C34—O10—C23—C24	165.0 (6)
C2—C1—C6—C5	3.8 (10)	C20—C19—C24—C23	0.0 (10)
C2—C1—C6—N1	−178.5 (6)	C20—C19—C24—N3	179.6 (6)
C4—C5—C6—C1	−3.1 (10)	C22—C23—C24—C19	0.5 (10)
O4—C5—C6—C1	177.7 (6)	O10—C23—C24—C19	−179.2 (5)
C4—C5—C6—N1	179.0 (6)	C22—C23—C24—N3	−179.1 (6)
O4—C5—C6—N1	−0.1 (9)	O10—C23—C24—N3	1.1 (9)
C7—N1—C6—C1	1.5 (10)	C25—N3—C24—C19	−1.0 (11)
C7—N1—C6—C5	179.2 (6)	C25—N3—C24—C23	178.6 (6)
C6—N1—C7—O1	1.7 (11)	C24—N3—C25—O7	−1.0 (12)
C6—N1—C7—C8	−179.2 (6)	C24—N3—C25—C26	179.2 (6)
C9—N2—C8—O2	−0.2 (12)	C27—N4—C26—O8	2.4 (12)
C9—N2—C8—C7	178.4 (5)	C27—N4—C26—C25	−178.4 (6)
O1—C7—C8—O2	178.6 (7)	O7—C25—C26—O8	179.6 (6)
N1—C7—C8—O2	−0.7 (9)	N3—C25—C26—O8	−0.5 (9)
O1—C7—C8—N2	−0.1 (8)	O7—C25—C26—N4	0.4 (9)
N1—C7—C8—N2	−179.4 (6)	N3—C25—C26—N4	−179.7 (6)
C8—N2—C9—C14	−1.2 (11)	C26—N4—C27—C28	178.8 (6)
C8—N2—C9—C10	178.5 (6)	C26—N4—C27—C32	−1.6 (11)
C17—O5—C10—C11	−10.0 (10)	C32—C27—C28—C29	−0.1 (9)
C17—O5—C10—C9	171.5 (6)	N4—C27—C28—C29	179.5 (6)
C14—C9—C10—C11	0.2 (10)	C32—C27—C28—O11	−179.5 (5)
N2—C9—C10—C11	−179.6 (6)	N4—C27—C28—O11	0.1 (8)
C14—C9—C10—O5	178.8 (6)	C35—O11—C28—C29	9.5 (9)
N2—C9—C10—O5	−0.9 (8)	C35—O11—C28—C27	−171.1 (6)
O5—C10—C11—C12	−178.0 (6)	C27—C28—C29—C30	−0.2 (10)
C9—C10—C11—C12	0.5 (10)	O11—C28—C29—C30	179.2 (6)
C10—C11—C12—C13	−1.1 (11)	C28—C29—C30—C31	1.7 (11)
C11—C12—C13—O6	179.5 (6)	C29—C30—C31—O12	179.5 (7)
C11—C12—C13—C14	1.1 (11)	C29—C30—C31—C32	−3.0 (11)
C18—O6—C13—C12	−0.7 (10)	C36—O12—C31—C30	1.0 (11)
C18—O6—C13—C14	177.7 (6)	C36—O12—C31—C32	−176.8 (6)
C10—C9—C14—C13	−0.1 (10)	C28—C27—C32—C31	−1.0 (9)
N2—C9—C14—C13	179.6 (6)	N4—C27—C32—C31	179.4 (6)
C12—C13—C14—C9	−0.5 (10)	C30—C31—C32—C27	2.6 (10)
O6—C13—C14—C9	−179.1 (6)	O12—C31—C32—C27	−179.5 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.86	2.23	2.665 (7)	112
N1—H1A···O4	0.86	2.20	2.615 (6)	109
N2—H2A···O1	0.86	2.22	2.657 (6)	112
N2—H2A···O5	0.86	2.19	2.607 (6)	110
N3—H3A···O8	0.86	2.21	2.656 (6)	112
N3—H3A···O10	0.86	2.19	2.604 (7)	110
N4—H4A···O7	0.86	2.22	2.663 (6)	112
N4—H4A···O11	0.86	2.18	2.599 (6)	110
C1—H1···O1	0.93	2.34	2.936 (7)	122
C14—H14···O2	0.93	2.32	2.923 (7)	122
C16—H16A···O3^i	0.96	2.47	3.367 (8)	155
C18—H18A···O9^ii	0.96	2.60	3.302 (8)	131
C19—H19···O7	0.93	2.34	2.945 (7)	122
C32—H32···O8	0.93	2.34	2.938 (7)	121
C34—H34A···O1	0.96	2.52	3.243 (8)	132
C35—H35A···O12^iii	0.96	2.31	3.228 (8)	160
C4—H4···Cg1^i	0.93	2.77	3.572	145
C12—H12···Cg2^iv	0.93	2.83	3.603	141

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