{2-[(1,5-Di­methyl-2-phenyl-3-oxo-2,3-di­hydro-1H-pyrazol-4-yl­imino)­methyl]­phenoxy}acetic acid methanol hemisolvate

The title compound, C₂₀H₁₉N₃O₄·0.5CH₃OH, has been synth­esized and characterized by elemental analysis and single-crystal X-ray diffraction. The dihedral angles between the pyrazoline ring and the unsubstituted ­phenyl ring are different [80.9 (2) and 55.7 (2)°, respectively] in the two crystallographically independent mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• R factor = 0.068
• wR factor = 0.123
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         38 Perc.
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors ....        C28

Alert level C
CELLV02_ALERT_1_C  The supplied cell volume s.u. differs from that
            calculated from the cell parameter s.u.'s by > 2
            Calculated cell volume su =      10.14
            Cell volume su given      =       7.00
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.95
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
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C10    -   C11     ..       5.44 su
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         O1
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C8
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C35    -C40           1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

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

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

{2-[(1,5-Dimethyl-2-phenyl-3-oxo-2,3-dihydro-1H-pyrazol-4- ylimino)methyl]phenoxy}acetic acid–methanol (2/1)

Crystal data

C20H19N3O4·0.5CH4O	Z = 4
Mr = 381.41	F(000) = 804
Triclinic, P1	Dx = 1.314 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.264 (2) Å	Cell parameters from 3180 reflections
b = 12.324 (3) Å	θ = 2.8–23.1°
c = 16.137 (3) Å	µ = 0.09 mm^−1
α = 98.05 (3)°	T = 293 K
β = 110.25 (3)°	Block, yellow
γ = 107.55 (3)°	0.31 × 0.22 × 0.13 mm
V = 1927.6 (7) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	7577 independent reflections
Radiation source: fine-focus sealed tube	2902 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
φ and ω scans	θmax = 26.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→13
Tmin = 0.971, Tmax = 0.988	k = −15→15
8968 measured reflections	l = −20→14

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	w = 1/[σ^2(Fo^2) + (0.0273P)^2] where P = (Fo^2 + 2Fc^2)/3
7577 reflections	(Δ/σ)max < 0.001
513 parameters	Δρmax = 0.18 e Å^−3
1 restraint	Δρmin = −0.18 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	0.3384 (3)	0.5134 (2)	0.47778 (18)	0.0800 (9)
O2	0.3570 (3)	0.3700 (2)	0.65947 (16)	0.0920 (9)
H2A	0.3663	0.3167	0.6289	0.138*
O3	0.3570 (3)	0.5470 (3)	0.6533 (2)	0.0979 (10)
O4	0.6156 (2)	0.80798 (19)	0.42363 (16)	0.0649 (7)
O5	0.5176 (3)	0.3186 (2)	0.86532 (18)	0.0851 (9)
O6	0.6741 (3)	0.4877 (2)	1.03009 (19)	0.0984 (11)
O7	0.6615 (3)	0.6293 (2)	0.96342 (18)	0.1229 (13)
H7C	0.7192	0.6724	1.0139	0.184*
O8	0.1949 (3)	0.0312 (2)	0.88442 (18)	0.0853 (9)
O9	0.1598 (4)	0.2271 (3)	0.8804 (2)	0.1250 (13)
N1	0.3152 (3)	0.7943 (2)	0.38448 (17)	0.0491 (8)
N2	0.6312 (3)	0.9875 (2)	0.39129 (19)	0.0588 (9)
N3	0.5489 (3)	1.0523 (2)	0.37423 (18)	0.0533 (8)
N4	0.4522 (3)	−0.0153 (3)	0.87472 (18)	0.0589 (9)
N5	0.1226 (3)	−0.1683 (3)	0.87198 (19)	0.0594 (9)
N6	0.1708 (3)	−0.2577 (3)	0.85894 (18)	0.0575 (8)
C1	0.2001 (3)	0.6066 (3)	0.3982 (2)	0.0465 (9)
C2	0.2084 (4)	0.5140 (3)	0.4375 (2)	0.0567 (10)
C3	0.0923 (4)	0.4298 (3)	0.4348 (2)	0.0634 (11)
H3A	0.0990	0.3695	0.4628	0.076*
C4	−0.0328 (4)	0.4359 (3)	0.3905 (3)	0.0672 (12)
H4A	−0.1109	0.3794	0.3886	0.081*
C5	−0.0438 (4)	0.5243 (4)	0.3491 (2)	0.0718 (12)
H5A	−0.1291	0.5269	0.3179	0.086*
C6	0.0716 (4)	0.6085 (3)	0.3542 (2)	0.0595 (11)
H6A	0.0636	0.6692	0.3271	0.071*
C7	0.3551 (4)	0.4251 (3)	0.5238 (3)	0.0690 (12)
H7A	0.4399	0.4163	0.5291	0.083*
H7B	0.2808	0.3500	0.4876	0.083*
C8	0.3572 (4)	0.4553 (4)	0.6184 (3)	0.0623 (11)
C9	0.3213 (3)	0.6986 (3)	0.4023 (2)	0.0525 (10)
H9A	0.4032	0.6869	0.4181	0.063*
C10	0.4290 (3)	0.8811 (3)	0.3851 (2)	0.0434 (9)
C11	0.5613 (4)	0.8810 (3)	0.4015 (2)	0.0523 (10)
C12	0.4258 (4)	0.9866 (3)	0.3675 (2)	0.0483 (9)
C13	0.3110 (3)	1.0280 (3)	0.3470 (2)	0.0671 (11)
H13A	0.2949	1.0513	0.2911	0.101*
H13B	0.3334	1.0943	0.3964	0.101*
H13C	0.2303	0.9651	0.3403	0.101*
C14	0.5909 (3)	1.1631 (3)	0.3508 (2)	0.0694 (12)
H14A	0.5259	1.1996	0.3483	0.104*
H14B	0.5951	1.1480	0.2921	0.104*
H14C	0.6793	1.2150	0.3967	0.104*
C15	0.7715 (4)	1.0352 (3)	0.4077 (3)	0.0490 (10)
C16	0.8666 (4)	1.1112 (3)	0.4915 (3)	0.0591 (11)
H16A	0.8393	1.1343	0.5370	0.071*
C17	1.0025 (4)	1.1527 (3)	0.5073 (3)	0.0695 (13)
H17A	1.0675	1.2039	0.5639	0.083*
C18	1.0430 (4)	1.1191 (3)	0.4403 (3)	0.0700 (13)
H18A	1.1352	1.1463	0.4517	0.084*
C19	0.9463 (4)	1.0447 (3)	0.3557 (3)	0.0721 (12)
H19A	0.9730	1.0227	0.3097	0.087*
C20	0.8108 (4)	1.0034 (3)	0.3400 (3)	0.0659 (12)
H20A	0.7455	0.9535	0.2830	0.079*
C21	0.6052 (4)	0.1687 (3)	0.8784 (2)	0.0593 (11)
C22	0.6233 (5)	0.2837 (4)	0.8688 (3)	0.0672 (12)
C23	0.7411 (5)	0.3521 (4)	0.8629 (3)	0.0863 (15)
H23A	0.7532	0.4283	0.8570	0.104*
C24	0.8395 (5)	0.3079 (5)	0.8657 (3)	0.0964 (16)
H24A	0.9178	0.3540	0.8609	0.116*
C25	0.8247 (5)	0.1965 (4)	0.8756 (3)	0.0892 (14)
H25A	0.8929	0.1675	0.8785	0.107*
C26	0.7083 (4)	0.1287 (4)	0.8810 (2)	0.0753 (13)
H26A	0.6980	0.0527	0.8868	0.090*
C27	0.5375 (4)	0.4397 (4)	0.8705 (3)	0.0876 (14)
H27A	0.4501	0.4483	0.8542	0.105*
H27B	0.5729	0.4632	0.8261	0.105*
C28	0.6343 (4)	0.5203 (4)	0.9643 (3)	0.0722 (13)
C29	0.4805 (4)	0.0966 (3)	0.8836 (2)	0.0619 (11)
H29A	0.4216	0.1308	0.8933	0.074*
C30	0.3306 (4)	−0.0879 (3)	0.8751 (2)	0.0526 (10)
C31	0.3003 (4)	−0.2065 (3)	0.8668 (2)	0.0523 (10)
C32	0.2174 (4)	−0.0621 (3)	0.8789 (2)	0.0575 (11)
C33	0.3888 (4)	−0.2739 (3)	0.8665 (2)	0.0741 (12)
H33A	0.3453	−0.3366	0.8106	0.111*
H33B	0.4037	−0.3067	0.9180	0.111*
H33C	0.4749	−0.2220	0.8707	0.111*
C34	0.1174 (3)	−0.3653 (3)	0.8845 (2)	0.0694 (12)
H34A	0.1701	−0.4130	0.8818	0.104*
H34B	0.0237	−0.4090	0.8427	0.104*
H34C	0.1232	−0.3445	0.9458	0.104*
C35	−0.0188 (4)	−0.1951 (4)	0.8470 (3)	0.0572 (11)
C36	−0.0609 (5)	−0.1419 (3)	0.9049 (3)	0.0761 (13)
H36A	0.0034	−0.0867	0.9599	0.091*
C37	−0.1974 (5)	−0.1690 (4)	0.8827 (4)	0.0902 (15)
H37A	−0.2258	−0.1315	0.9220	0.108*
C38	−0.2916 (5)	−0.2516 (5)	0.8022 (4)	0.0888 (16)
H38A	−0.3844	−0.2711	0.7873	0.107*
C39	−0.2505 (5)	−0.3053 (4)	0.7441 (3)	0.0910 (15)
H39A	−0.3149	−0.3610	0.6893	0.109*
C40	−0.1132 (5)	−0.2770 (4)	0.7663 (3)	0.0817 (14)
H40A	−0.0848	−0.3136	0.7266	0.098*
C41	0.1441 (4)	0.2554 (4)	0.7992 (3)	0.1163 (19)
H41A	0.1316	0.3294	0.8026	0.174*
H41B	0.0656	0.1945	0.7500	0.174*
H41C	0.2240	0.2622	0.7880	0.174*
H9B	0.159 (5)	0.1529 (19)	0.873 (3)	0.17 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0709 (18)	0.0682 (19)	0.138 (3)	0.0368 (15)	0.0605 (18)	0.0683 (18)
O2	0.126 (2)	0.091 (2)	0.0621 (19)	0.0524 (19)	0.0292 (17)	0.0275 (17)
O3	0.088 (2)	0.064 (2)	0.116 (3)	0.0305 (18)	0.0230 (18)	−0.0098 (19)
O4	0.0572 (16)	0.0453 (15)	0.092 (2)	0.0220 (13)	0.0229 (14)	0.0336 (15)
O5	0.083 (2)	0.0525 (19)	0.110 (2)	0.0181 (17)	0.0338 (18)	0.0246 (17)
O6	0.151 (3)	0.071 (2)	0.079 (2)	0.0513 (19)	0.037 (2)	0.0388 (18)
O7	0.186 (3)	0.058 (2)	0.091 (2)	0.034 (2)	0.023 (2)	0.0353 (18)
O8	0.098 (2)	0.0459 (18)	0.119 (2)	0.0344 (16)	0.0478 (18)	0.0213 (17)
O9	0.178 (3)	0.067 (3)	0.105 (3)	0.056 (2)	0.025 (2)	0.016 (2)
N1	0.0498 (18)	0.0407 (18)	0.051 (2)	0.0120 (15)	0.0160 (15)	0.0178 (16)
N2	0.049 (2)	0.046 (2)	0.081 (2)	0.0177 (17)	0.0216 (17)	0.0288 (18)
N3	0.053 (2)	0.0383 (18)	0.073 (2)	0.0183 (16)	0.0248 (17)	0.0281 (17)
N4	0.063 (2)	0.048 (2)	0.053 (2)	0.0160 (18)	0.0142 (17)	0.0106 (18)
N5	0.063 (2)	0.044 (2)	0.075 (2)	0.0246 (19)	0.0295 (18)	0.0143 (18)
N6	0.065 (2)	0.046 (2)	0.066 (2)	0.0221 (18)	0.0291 (18)	0.0180 (17)
C1	0.045 (2)	0.038 (2)	0.048 (2)	0.0069 (18)	0.0186 (19)	0.0090 (19)
C2	0.060 (3)	0.045 (2)	0.077 (3)	0.017 (2)	0.042 (2)	0.022 (2)
C3	0.074 (3)	0.046 (2)	0.085 (3)	0.022 (2)	0.046 (3)	0.024 (2)
C4	0.057 (3)	0.054 (3)	0.072 (3)	−0.006 (2)	0.034 (2)	0.006 (2)
C5	0.051 (3)	0.076 (3)	0.070 (3)	0.008 (2)	0.019 (2)	0.013 (3)
C6	0.054 (2)	0.055 (3)	0.054 (3)	0.011 (2)	0.014 (2)	0.011 (2)
C7	0.076 (3)	0.055 (3)	0.109 (4)	0.035 (2)	0.057 (3)	0.046 (3)
C8	0.047 (2)	0.054 (3)	0.066 (3)	0.011 (2)	0.011 (2)	0.006 (3)
C9	0.048 (2)	0.051 (2)	0.061 (3)	0.018 (2)	0.0224 (19)	0.023 (2)
C10	0.044 (2)	0.041 (2)	0.042 (2)	0.0132 (19)	0.0158 (18)	0.0166 (18)
C11	0.057 (3)	0.039 (2)	0.052 (3)	0.013 (2)	0.015 (2)	0.021 (2)
C12	0.049 (2)	0.051 (2)	0.047 (2)	0.018 (2)	0.0212 (19)	0.016 (2)
C13	0.064 (3)	0.060 (3)	0.089 (3)	0.028 (2)	0.036 (2)	0.034 (2)
C14	0.075 (3)	0.052 (2)	0.093 (3)	0.026 (2)	0.038 (2)	0.040 (2)
C15	0.039 (2)	0.040 (2)	0.061 (3)	0.0098 (19)	0.014 (2)	0.023 (2)
C16	0.067 (3)	0.043 (2)	0.060 (3)	0.010 (2)	0.026 (2)	0.017 (2)
C17	0.063 (3)	0.050 (3)	0.069 (3)	0.003 (2)	0.013 (3)	0.017 (2)
C18	0.048 (3)	0.046 (3)	0.107 (4)	0.008 (2)	0.026 (3)	0.032 (3)
C19	0.073 (3)	0.069 (3)	0.082 (4)	0.025 (3)	0.041 (3)	0.023 (3)
C20	0.057 (3)	0.063 (3)	0.061 (3)	0.011 (2)	0.016 (2)	0.014 (2)
C21	0.055 (3)	0.056 (3)	0.054 (3)	0.011 (2)	0.021 (2)	0.007 (2)
C22	0.071 (3)	0.055 (3)	0.066 (3)	0.018 (3)	0.025 (2)	0.012 (2)
C23	0.097 (4)	0.064 (3)	0.093 (4)	0.012 (3)	0.049 (3)	0.022 (3)
C24	0.109 (4)	0.086 (4)	0.090 (4)	0.011 (3)	0.063 (3)	0.008 (3)
C25	0.078 (3)	0.088 (4)	0.097 (4)	0.023 (3)	0.044 (3)	0.010 (3)
C26	0.068 (3)	0.073 (3)	0.082 (3)	0.017 (3)	0.038 (3)	0.016 (3)
C27	0.099 (3)	0.062 (3)	0.080 (4)	0.020 (3)	0.019 (3)	0.022 (3)
C28	0.094 (3)	0.050 (3)	0.076 (4)	0.027 (3)	0.034 (3)	0.030 (3)
C29	0.059 (3)	0.058 (3)	0.053 (3)	0.015 (2)	0.014 (2)	0.007 (2)
C30	0.048 (2)	0.051 (3)	0.050 (3)	0.017 (2)	0.012 (2)	0.015 (2)
C31	0.056 (3)	0.051 (3)	0.051 (3)	0.023 (2)	0.021 (2)	0.013 (2)
C32	0.068 (3)	0.041 (3)	0.059 (3)	0.020 (2)	0.022 (2)	0.014 (2)
C33	0.073 (3)	0.064 (3)	0.097 (3)	0.033 (2)	0.040 (2)	0.026 (2)
C34	0.087 (3)	0.051 (3)	0.075 (3)	0.026 (2)	0.037 (2)	0.024 (2)
C35	0.060 (3)	0.059 (3)	0.060 (3)	0.026 (2)	0.029 (3)	0.017 (2)
C36	0.081 (4)	0.071 (3)	0.082 (4)	0.036 (3)	0.037 (3)	0.013 (3)
C37	0.098 (4)	0.100 (4)	0.111 (5)	0.058 (3)	0.064 (3)	0.042 (4)
C38	0.072 (3)	0.110 (5)	0.105 (5)	0.043 (3)	0.041 (4)	0.061 (4)
C39	0.071 (4)	0.123 (4)	0.064 (4)	0.026 (3)	0.023 (3)	0.017 (3)
C40	0.068 (3)	0.103 (4)	0.067 (3)	0.024 (3)	0.030 (3)	0.013 (3)
C41	0.132 (4)	0.088 (4)	0.094 (4)	0.048 (3)	0.003 (3)	0.021 (3)

Geometric parameters (Å, º)

O1—C2	1.383 (4)	C14—H14C	0.96
O1—C7	1.423 (3)	C15—C20	1.365 (5)
O2—C8	1.320 (4)	C15—C16	1.375 (4)
O2—H2A	0.82	C16—C17	1.376 (5)
O3—C8	1.191 (4)	C16—H16A	0.93
O4—C11	1.258 (4)	C17—C18	1.370 (5)
O5—C22	1.369 (4)	C17—H17A	0.93
O5—C27	1.427 (4)	C18—C19	1.381 (5)
O6—C28	1.179 (4)	C18—H18A	0.93
O7—C28	1.288 (4)	C19—C20	1.371 (5)
O7—H7C	0.82	C19—H19A	0.93
O8—C32	1.247 (4)	C20—H20A	0.93
O9—C41	1.370 (4)	C21—C26	1.382 (5)
O9—H9B	0.90 (3)	C21—C22	1.408 (5)
N1—C9	1.268 (3)	C21—C29	1.456 (4)
N1—C10	1.396 (4)	C22—C23	1.384 (5)
N2—C11	1.378 (4)	C23—C24	1.366 (5)
N2—N3	1.379 (3)	C23—H23A	0.93
N2—C15	1.422 (4)	C24—C25	1.371 (5)
N3—C12	1.336 (4)	C24—H24A	0.93
N3—C14	1.453 (3)	C25—C26	1.365 (5)
N4—C29	1.293 (4)	C25—H25A	0.93
N4—C30	1.394 (4)	C26—H26A	0.93
N5—C32	1.379 (4)	C27—C28	1.501 (5)
N5—N6	1.389 (3)	C27—H27A	0.97
N5—C35	1.417 (4)	C27—H27B	0.97
N6—C31	1.354 (4)	C29—H29A	0.93
N6—C34	1.461 (4)	C30—C31	1.372 (4)
C1—C6	1.383 (4)	C30—C32	1.423 (5)
C1—C2	1.393 (4)	C31—C33	1.479 (4)
C1—C9	1.462 (4)	C33—H33A	0.96
C2—C3	1.385 (4)	C33—H33B	0.96
C3—C4	1.372 (4)	C33—H33C	0.96
C3—H3A	0.93	C34—H34A	0.96
C4—C5	1.370 (4)	C34—H34B	0.96
C4—H4A	0.93	C34—H34C	0.96
C5—C6	1.365 (4)	C35—C36	1.360 (5)
C5—H5A	0.93	C35—C40	1.367 (4)
C6—H6A	0.93	C36—C37	1.371 (5)
C7—C8	1.509 (5)	C36—H36A	0.93
C7—H7A	0.97	C37—C38	1.369 (5)
C7—H7B	0.97	C37—H37A	0.93
C9—H9A	0.93	C38—C39	1.358 (5)
C10—C12	1.377 (4)	C38—H38A	0.93
C10—C11	1.421 (4)	C39—C40	1.377 (5)
C12—C13	1.480 (4)	C39—H39A	0.93
C13—H13A	0.96	C40—H40A	0.93
C13—H13B	0.96	C41—H41A	0.96
C13—H13C	0.96	C41—H41B	0.96
C14—H14A	0.96	C41—H41C	0.96
C14—H14B	0.96
C2—O1—C7	118.1 (3)	C20—C19—C18	119.8 (4)
C8—O2—H2A	109.5	C20—C19—H19A	120.1
C22—O5—C27	118.2 (3)	C18—C19—H19A	120.1
C28—O7—H7C	109.5	C15—C20—C19	120.1 (4)
C41—O9—H9B	108 (3)	C15—C20—H20A	119.9
C9—N1—C10	120.9 (3)	C19—C20—H20A	119.9
C11—N2—N3	109.4 (3)	C26—C21—C22	117.3 (4)
C11—N2—C15	127.4 (3)	C26—C21—C29	122.8 (4)
N3—N2—C15	122.6 (3)	C22—C21—C29	119.9 (4)
C12—N3—N2	108.7 (3)	O5—C22—C23	124.8 (4)
C12—N3—C14	128.9 (3)	O5—C22—C21	115.2 (4)
N2—N3—C14	121.4 (3)	C23—C22—C21	120.1 (4)
C29—N4—C30	121.0 (3)	C24—C23—C22	120.0 (5)
C32—N5—N6	109.2 (3)	C24—C23—H23A	120.0
C32—N5—C35	126.2 (3)	C22—C23—H23A	120.0
N6—N5—C35	120.7 (3)	C23—C24—C25	121.0 (5)
C31—N6—N5	107.7 (3)	C23—C24—H24A	119.5
C31—N6—C34	125.8 (3)	C25—C24—H24A	119.5
N5—N6—C34	118.4 (3)	C26—C25—C24	119.0 (5)
C6—C1—C2	117.4 (3)	C26—C25—H25A	120.5
C6—C1—C9	120.6 (3)	C24—C25—H25A	120.5
C2—C1—C9	122.0 (3)	C25—C26—C21	122.6 (4)
O1—C2—C3	124.0 (3)	C25—C26—H26A	118.7
O1—C2—C1	115.3 (3)	C21—C26—H26A	118.7
C3—C2—C1	120.7 (4)	O5—C27—C28	112.4 (3)
C4—C3—C2	119.5 (4)	O5—C27—H27A	109.1
C4—C3—H3A	120.2	C28—C27—H27A	109.1
C2—C3—H3A	120.2	O5—C27—H27B	109.1
C5—C4—C3	120.7 (4)	C28—C27—H27B	109.1
C5—C4—H4A	119.6	H27A—C27—H27B	107.8
C3—C4—H4A	119.6	O6—C28—O7	125.2 (5)
C6—C5—C4	119.3 (4)	O6—C28—C27	124.3 (4)
C6—C5—H5A	120.4	O7—C28—C27	110.4 (4)
C4—C5—H5A	120.4	N4—C29—C21	119.6 (4)
C5—C6—C1	122.3 (4)	N4—C29—H29A	120.2
C5—C6—H6A	118.9	C21—C29—H29A	120.2
C1—C6—H6A	118.9	C31—C30—N4	121.5 (4)
O1—C7—C8	112.1 (3)	C31—C30—C32	107.9 (3)
O1—C7—H7A	109.2	N4—C30—C32	130.5 (4)
C8—C7—H7A	109.2	N6—C31—C30	109.1 (3)
O1—C7—H7B	109.2	N6—C31—C33	122.6 (3)
C8—C7—H7B	109.2	C30—C31—C33	128.3 (4)
H7A—C7—H7B	107.9	O8—C32—N5	122.1 (4)
O3—C8—O2	122.1 (5)	O8—C32—C30	132.2 (4)
O3—C8—C7	123.7 (4)	N5—C32—C30	105.6 (3)
O2—C8—C7	114.1 (4)	C31—C33—H33A	109.5
N1—C9—C1	120.3 (3)	C31—C33—H33B	109.5
N1—C9—H9A	119.9	H33A—C33—H33B	109.5
C1—C9—H9A	119.9	C31—C33—H33C	109.5
C12—C10—N1	122.0 (3)	H33A—C33—H33C	109.5
C12—C10—C11	108.3 (3)	H33B—C33—H33C	109.5
N1—C10—C11	129.7 (3)	N6—C34—H34A	109.5
O4—C11—N2	122.7 (3)	N6—C34—H34B	109.5
O4—C11—C10	132.4 (3)	H34A—C34—H34B	109.5
N2—C11—C10	104.9 (3)	N6—C34—H34C	109.5
N3—C12—C10	108.6 (3)	H34A—C34—H34C	109.5
N3—C12—C13	123.0 (3)	H34B—C34—H34C	109.5
C10—C12—C13	128.4 (3)	C36—C35—C40	119.9 (4)
C12—C13—H13A	109.5	C36—C35—N5	119.8 (4)
C12—C13—H13B	109.5	C40—C35—N5	120.3 (4)
H13A—C13—H13B	109.5	C35—C36—C37	120.5 (4)
C12—C13—H13C	109.5	C35—C36—H36A	119.7
H13A—C13—H13C	109.5	C37—C36—H36A	119.7
H13B—C13—H13C	109.5	C38—C37—C36	119.5 (5)
N3—C14—H14A	109.5	C38—C37—H37A	120.3
N3—C14—H14B	109.5	C36—C37—H37A	120.3
H14A—C14—H14B	109.5	C39—C38—C37	120.4 (5)
N3—C14—H14C	109.5	C39—C38—H38A	119.8
H14A—C14—H14C	109.5	C37—C38—H38A	119.8
H14B—C14—H14C	109.5	C38—C39—C40	119.9 (5)
C20—C15—C16	120.6 (4)	C38—C39—H39A	120.0
C20—C15—N2	119.3 (4)	C40—C39—H39A	120.0
C16—C15—N2	120.1 (4)	C35—C40—C39	119.9 (4)
C15—C16—C17	119.3 (4)	C35—C40—H40A	120.1
C15—C16—H16A	120.4	C39—C40—H40A	120.1
C17—C16—H16A	120.4	O9—C41—H41A	109.5
C18—C17—C16	120.5 (4)	O9—C41—H41B	109.5
C18—C17—H17A	119.8	H41A—C41—H41B	109.5
C16—C17—H17A	119.8	O9—C41—H41C	109.5
C17—C18—C19	119.7 (4)	H41A—C41—H41C	109.5
C17—C18—H18A	120.1	H41B—C41—H41C	109.5
C19—C18—H18A	120.1
C11—N2—N3—C12	−3.9 (4)	C17—C18—C19—C20	−1.1 (6)
C15—N2—N3—C12	−176.0 (3)	C16—C15—C20—C19	1.7 (5)
C11—N2—N3—C14	−173.3 (3)	N2—C15—C20—C19	−177.4 (3)
C15—N2—N3—C14	14.6 (5)	C18—C19—C20—C15	−0.3 (6)
C32—N5—N6—C31	6.0 (4)	C27—O5—C22—C23	−10.4 (6)
C35—N5—N6—C31	165.2 (3)	C27—O5—C22—C21	170.2 (3)
C32—N5—N6—C34	156.8 (3)	C26—C21—C22—O5	179.1 (3)
C35—N5—N6—C34	−44.1 (4)	C29—C21—C22—O5	0.1 (5)
C7—O1—C2—C3	−3.8 (5)	C26—C21—C22—C23	−0.3 (5)
C7—O1—C2—C1	176.4 (3)	C29—C21—C22—C23	−179.4 (3)
C6—C1—C2—O1	177.7 (3)	O5—C22—C23—C24	−178.9 (4)
C9—C1—C2—O1	−2.0 (5)	C21—C22—C23—C24	0.5 (6)
C6—C1—C2—C3	−2.1 (5)	C22—C23—C24—C25	−0.9 (7)
C9—C1—C2—C3	178.2 (3)	C23—C24—C25—C26	1.1 (7)
O1—C2—C3—C4	−177.8 (4)	C24—C25—C26—C21	−1.0 (6)
C1—C2—C3—C4	1.9 (6)	C22—C21—C26—C25	0.6 (6)
C2—C3—C4—C5	0.0 (6)	C29—C21—C26—C25	179.6 (3)
C3—C4—C5—C6	−1.6 (6)	C22—O5—C27—C28	−70.8 (4)
C4—C5—C6—C1	1.4 (6)	O5—C27—C28—O6	−10.7 (6)
C2—C1—C6—C5	0.5 (6)	O5—C27—C28—O7	172.7 (4)
C9—C1—C6—C5	−179.9 (3)	C30—N4—C29—C21	−177.0 (3)
C2—O1—C7—C8	−79.1 (4)	C26—C21—C29—N4	−12.2 (5)
O1—C7—C8—O3	−6.2 (6)	C22—C21—C29—N4	166.8 (3)
O1—C7—C8—O2	172.7 (3)	C29—N4—C30—C31	−179.2 (3)
C10—N1—C9—C1	−177.8 (3)	C29—N4—C30—C32	4.2 (5)
C6—C1—C9—N1	15.9 (5)	N5—N6—C31—C30	−6.2 (4)
C2—C1—C9—N1	−164.5 (3)	C34—N6—C31—C30	−154.2 (3)
C9—N1—C10—C12	−178.8 (3)	N5—N6—C31—C33	173.5 (3)
C9—N1—C10—C11	1.7 (5)	C34—N6—C31—C33	25.5 (5)
N3—N2—C11—O4	−175.2 (3)	N4—C30—C31—N6	−173.2 (3)
C15—N2—C11—O4	−3.5 (6)	C32—C30—C31—N6	4.1 (4)
N3—N2—C11—C10	2.9 (4)	N4—C30—C31—C33	7.1 (6)
C15—N2—C11—C10	174.6 (3)	C32—C30—C31—C33	−175.5 (3)
C12—C10—C11—O4	176.9 (4)	N6—N5—C32—O8	174.9 (3)
N1—C10—C11—O4	−3.6 (6)	C35—N5—C32—O8	17.2 (6)
C12—C10—C11—N2	−1.0 (4)	N6—N5—C32—C30	−3.4 (4)
N1—C10—C11—N2	178.6 (3)	C35—N5—C32—C30	−161.1 (3)
N2—N3—C12—C10	3.2 (4)	C31—C30—C32—O8	−178.4 (4)
C14—N3—C12—C10	171.6 (3)	N4—C30—C32—O8	−1.4 (7)
N2—N3—C12—C13	−178.4 (3)	C31—C30—C32—N5	−0.4 (4)
C14—N3—C12—C13	−10.0 (6)	N4—C30—C32—N5	176.6 (3)
N1—C10—C12—N3	179.0 (3)	C32—N5—C35—C36	−68.9 (5)
C11—C10—C12—N3	−1.4 (4)	N6—N5—C35—C36	135.7 (4)
N1—C10—C12—C13	0.8 (5)	C32—N5—C35—C40	113.3 (4)
C11—C10—C12—C13	−179.6 (3)	N6—N5—C35—C40	−42.1 (5)
C11—N2—C15—C20	85.1 (4)	C40—C35—C36—C37	−0.5 (6)
N3—N2—C15—C20	−104.3 (4)	N5—C35—C36—C37	−178.4 (3)
C11—N2—C15—C16	−94.1 (4)	C35—C36—C37—C38	1.0 (6)
N3—N2—C15—C16	76.6 (4)	C36—C37—C38—C39	−0.9 (7)
C20—C15—C16—C17	−1.7 (5)	C37—C38—C39—C40	0.4 (7)
N2—C15—C16—C17	177.4 (3)	C36—C35—C40—C39	0.0 (6)
C15—C16—C17—C18	0.3 (5)	N5—C35—C40—C39	177.9 (4)
C16—C17—C18—C19	1.1 (6)	C38—C39—C40—C35	0.1 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9B···O8	0.90 (3)	1.69 (4)	2.567 (5)	165 (4)
O7—H7C···O9^i	0.82	1.76	2.574 (5)	176
O2—H2A···O4^ii	0.82	1.75	2.564 (4)	171
C7—H7A···O1^ii	0.97	2.43	3.314 (6)	151
C9—H9A···O4	0.93	2.37	3.051 (5)	130
C29—H29A···O8	0.93	2.42	3.077 (6)	128
C33—H33B···O6^iii	0.96	2.51	3.340 (4)	145
C34—H34A···O6^iii	0.96	2.36	3.189 (5)	144

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