4-{[1-(Methoxycarbonyl)ethylamino](phen­yl)methyl­idene}-3-meth­yl-1-phenyl­-1H-pyrazol-5(4H)-one

The title compound, C₂₁H₂₁N₃O₃, is a neutral potentially tridentate ligand in an enamine-keto form, stabilized by an intra­molecular N—H...O hydrogen bond. There are two mol­ecules in the asymmetric unit.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.042
• wR factor = 0.110
• Data-to-parameter ratio = 7.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.33
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.55 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C2     -   C3      ..       5.86 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C35
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C18
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C20
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C33
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C33    -C38           1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

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           25.03
           From the CIF: _reflns_number_total               3620
           Count of symmetry unique reflns         3640
           Completeness (_total/calc)             99.45%
           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

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

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

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Computing details

Data collection: APEX2 (Bruker, 2003); cell refinement: APEX2; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

4-{[(2-alanine methyl ester)amino](phenyl)methylidene} -3-methyl-1-phenylpyrazol-5-one

Crystal data

C21H21N3O3	F(000) = 768
Mr = 363.41	Dx = 1.234 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1621 reflections
a = 8.8118 (18) Å	θ = 2.3–17.6°
b = 12.430 (3) Å	µ = 0.08 mm^−1
c = 18.031 (4) Å	T = 293 K
β = 97.749 (2)°	Block, pale yellow
V = 1956.9 (7) Å^3	0.38 × 0.32 × 0.20 mm
Z = 4

Data collection

Bruker APEX2 CCD area detector diffractometer	3620 independent reflections
Radiation source: fine-focus sealed tube	2191 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.934, Tmax = 0.987	k = −14→14
10774 measured reflections	l = −21→17

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)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0458P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
3620 reflections	Δρmax = 0.13 e Å^−3
494 parameters	Δρmin = −0.15 e Å^−3
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (2)

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	0.7418 (4)	0.6456 (3)	0.39995 (19)	0.0855 (9)
O2	0.5539 (5)	0.8983 (3)	0.4527 (2)	0.1185 (14)
O3	0.5837 (4)	1.0731 (3)	0.4333 (2)	0.1065 (12)
O4	0.2892 (3)	0.6953 (2)	0.11451 (16)	0.0673 (8)
O5	0.0729 (4)	0.4449 (3)	0.0422 (2)	0.0908 (10)
O6	0.1036 (4)	0.2685 (2)	0.06132 (19)	0.0844 (9)
N1	0.9688 (5)	0.5559 (3)	0.3845 (2)	0.0742 (10)
N2	1.1069 (5)	0.5800 (3)	0.3584 (2)	0.0778 (11)
N3	0.7633 (4)	0.8544 (3)	0.3588 (2)	0.0774 (11)
H3	0.7179	0.8033	0.3793	0.093*
N4	0.5313 (4)	0.7738 (2)	0.12058 (19)	0.0601 (9)
N5	0.6849 (4)	0.7412 (3)	0.1375 (2)	0.0670 (10)
N6	0.3183 (4)	0.4833 (3)	0.1498 (2)	0.0655 (9)
H6	0.2624	0.5398	0.1409	0.079*
C1	1.0678 (7)	0.3802 (5)	0.4208 (3)	0.1020 (17)
H1	1.1614	0.3998	0.4064	0.122*
C2	1.0477 (9)	0.2774 (5)	0.4486 (3)	0.114 (2)
H2	1.1282	0.2283	0.4526	0.137*
C3	0.9112 (10)	0.2481 (5)	0.4699 (3)	0.114 (2)
H3A	0.8973	0.1790	0.4875	0.137*
C4	0.7964 (8)	0.3202 (5)	0.4653 (3)	0.112 (2)
H4	0.7041	0.3004	0.4810	0.134*
C5	0.8124 (7)	0.4239 (4)	0.4377 (3)	0.0953 (16)
H5	0.7318	0.4727	0.4350	0.114*
C6	0.9488 (7)	0.4528 (4)	0.4146 (2)	0.0757 (13)
C7	1.0980 (5)	0.6807 (4)	0.3363 (2)	0.0719 (12)
C8	1.2313 (6)	0.7295 (4)	0.3057 (3)	0.0948 (16)
H8A	1.3110	0.6769	0.3059	0.142*
H8B	1.2689	0.7897	0.3362	0.142*
H8C	1.1997	0.7535	0.2554	0.142*
C9	0.9534 (5)	0.7273 (4)	0.3476 (2)	0.0687 (12)
C10	0.8719 (6)	0.6428 (4)	0.3803 (3)	0.0739 (12)
C11	0.8967 (5)	0.8301 (4)	0.3374 (2)	0.0620 (11)
C12	0.9803 (5)	0.9150 (3)	0.3015 (2)	0.0601 (11)
C13	1.0778 (5)	0.9850 (4)	0.3428 (3)	0.0808 (14)
H13	1.0910	0.9817	0.3948	0.097*
C14	1.1569 (6)	1.0611 (4)	0.3064 (4)	0.0929 (16)
H14	1.2226	1.1093	0.3341	0.111*
C15	1.1385 (6)	1.0653 (4)	0.2301 (4)	0.0875 (16)
H15	1.1946	1.1146	0.2061	0.105*
C16	1.0387 (5)	0.9979 (4)	0.1888 (3)	0.0773 (13)
H16	1.0244	1.0025	0.1369	0.093*
C17	0.9588 (5)	0.9228 (3)	0.2245 (3)	0.0672 (11)
H17	0.8899	0.8771	0.1964	0.081*
C18	0.6845 (5)	0.9565 (4)	0.3519 (3)	0.0699 (12)
H18	0.7602	1.0142	0.3516	0.084*
C19	0.5713 (6)	0.9635 (5)	0.2807 (3)	0.1013 (17)
H19A	0.6260	0.9667	0.2382	0.152*
H19B	0.5098	1.0271	0.2822	0.152*
H19C	0.5063	0.9012	0.2768	0.152*
C20	0.6019 (5)	0.9709 (4)	0.4181 (3)	0.0793 (14)
C21	0.4987 (9)	1.0981 (6)	0.4945 (4)	0.153 (3)
H21A	0.4035	1.0594	0.4881	0.229*
H21B	0.4785	1.1739	0.4951	0.229*
H21C	0.5577	1.0774	0.5410	0.229*
C22	0.3566 (5)	0.9234 (3)	0.0893 (2)	0.0671 (12)
H22	0.2777	0.8856	0.1069	0.081*
C23	0.3325 (6)	1.0260 (3)	0.0609 (3)	0.0764 (13)
H23	0.2363	1.0573	0.0598	0.092*
C24	0.4470 (6)	1.0830 (3)	0.0343 (2)	0.0749 (13)
H24	0.4291	1.1523	0.0157	0.090*
C25	0.5864 (6)	1.0369 (4)	0.0355 (2)	0.0730 (12)
H25	0.6644	1.0750	0.0173	0.088*
C26	0.6148 (5)	0.9345 (3)	0.0632 (2)	0.0633 (11)
H26	0.7109	0.9037	0.0629	0.076*
C27	0.5007 (5)	0.8776 (3)	0.0911 (2)	0.0539 (10)
C28	0.4307 (5)	0.6910 (3)	0.1287 (2)	0.0554 (10)
C29	0.5272 (4)	0.6008 (3)	0.1534 (2)	0.0520 (10)
C30	0.6805 (5)	0.6390 (3)	0.1584 (2)	0.0618 (11)
C31	0.8291 (5)	0.5815 (4)	0.1785 (3)	0.0847 (15)
H31A	0.9116	0.6325	0.1826	0.127*
H31B	0.8422	0.5298	0.1403	0.127*
H31C	0.8290	0.5452	0.2255	0.127*
C32	0.4695 (5)	0.4988 (3)	0.1615 (2)	0.0565 (10)
C33	0.5680 (4)	0.4040 (3)	0.1815 (2)	0.0565 (10)
C34	0.5924 (6)	0.3663 (4)	0.2521 (3)	0.0916 (16)
H34	0.5472	0.4012	0.2892	0.110*
C35	0.6832 (8)	0.2769 (5)	0.2709 (4)	0.1138 (19)
H35	0.6986	0.2518	0.3199	0.137*
C36	0.7490 (6)	0.2266 (4)	0.2172 (5)	0.1009 (18)
H36	0.8103	0.1666	0.2294	0.121*
C37	0.7268 (6)	0.2624 (4)	0.1454 (4)	0.0907 (16)
H37	0.7730	0.2273	0.1088	0.109*
C38	0.6347 (5)	0.3518 (4)	0.1269 (3)	0.0719 (12)
H38	0.6183	0.3762	0.0777	0.086*
C39	0.2379 (4)	0.3814 (3)	0.1505 (2)	0.0615 (11)
H39	0.3123	0.3225	0.1533	0.074*
C40	0.1488 (5)	0.3748 (4)	0.2181 (3)	0.0839 (14)
H40A	0.2196	0.3682	0.2633	0.126*
H40B	0.0824	0.3132	0.2129	0.126*
H40C	0.0887	0.4388	0.2204	0.126*
C41	0.1296 (5)	0.3717 (4)	0.0793 (3)	0.0664 (11)
C42	−0.0004 (6)	0.2460 (5)	−0.0078 (3)	0.1021 (17)
H42A	−0.0913	0.2889	−0.0087	0.153*
H42B	−0.0276	0.1712	−0.0093	0.153*
H42C	0.0496	0.2634	−0.0503	0.153*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.094 (2)	0.071 (2)	0.100 (3)	−0.0092 (17)	0.043 (2)	0.0039 (16)
O2	0.149 (3)	0.095 (3)	0.129 (3)	−0.008 (3)	0.080 (3)	0.001 (2)
O3	0.126 (3)	0.078 (3)	0.130 (3)	−0.012 (2)	0.067 (3)	−0.026 (2)
O4	0.0565 (17)	0.0520 (16)	0.092 (2)	0.0026 (14)	0.0061 (15)	0.0060 (15)
O5	0.091 (2)	0.069 (2)	0.106 (3)	0.0088 (18)	−0.0097 (19)	0.011 (2)
O6	0.088 (2)	0.060 (2)	0.101 (3)	−0.0025 (17)	−0.0034 (18)	−0.0037 (18)
N1	0.096 (3)	0.057 (2)	0.075 (3)	0.001 (2)	0.029 (2)	−0.002 (2)
N2	0.094 (3)	0.067 (3)	0.078 (3)	0.009 (2)	0.030 (2)	0.000 (2)
N3	0.079 (2)	0.065 (3)	0.095 (3)	−0.004 (2)	0.038 (2)	0.007 (2)
N4	0.057 (2)	0.046 (2)	0.076 (2)	0.0003 (17)	0.0039 (17)	−0.0026 (18)
N5	0.054 (2)	0.059 (2)	0.084 (3)	−0.0006 (17)	−0.0040 (18)	−0.0033 (18)
N6	0.059 (2)	0.047 (2)	0.089 (3)	0.0081 (18)	0.0047 (19)	0.0074 (17)
C1	0.140 (5)	0.082 (4)	0.085 (4)	0.007 (4)	0.022 (3)	0.016 (3)
C2	0.151 (6)	0.084 (4)	0.110 (5)	0.022 (4)	0.031 (4)	0.029 (4)
C3	0.186 (7)	0.070 (4)	0.080 (4)	−0.001 (5)	−0.003 (4)	0.015 (3)
C4	0.147 (5)	0.078 (4)	0.109 (5)	−0.022 (4)	0.010 (4)	0.012 (3)
C5	0.118 (4)	0.067 (3)	0.105 (4)	−0.012 (3)	0.029 (3)	0.010 (3)
C6	0.117 (4)	0.056 (3)	0.054 (3)	0.004 (3)	0.013 (3)	−0.005 (2)
C7	0.091 (3)	0.067 (3)	0.062 (3)	0.000 (3)	0.023 (2)	0.000 (2)
C8	0.096 (4)	0.087 (4)	0.111 (4)	0.004 (3)	0.046 (3)	0.007 (3)
C9	0.081 (3)	0.062 (3)	0.068 (3)	−0.005 (2)	0.029 (2)	−0.001 (2)
C10	0.097 (4)	0.062 (3)	0.067 (3)	−0.006 (3)	0.024 (3)	−0.005 (2)
C11	0.067 (3)	0.062 (3)	0.059 (3)	−0.003 (2)	0.017 (2)	−0.003 (2)
C12	0.061 (2)	0.056 (3)	0.066 (3)	−0.004 (2)	0.019 (2)	−0.003 (2)
C13	0.085 (3)	0.085 (4)	0.075 (3)	−0.018 (3)	0.020 (3)	−0.012 (3)
C14	0.083 (3)	0.079 (4)	0.118 (5)	−0.018 (3)	0.018 (3)	−0.016 (4)
C15	0.084 (4)	0.062 (3)	0.123 (5)	−0.003 (3)	0.040 (3)	0.006 (3)
C16	0.081 (3)	0.072 (3)	0.085 (4)	0.002 (3)	0.035 (3)	0.013 (3)
C17	0.074 (3)	0.062 (3)	0.068 (3)	−0.004 (2)	0.019 (2)	0.006 (2)
C18	0.068 (3)	0.060 (3)	0.086 (4)	0.000 (2)	0.027 (3)	0.001 (2)
C19	0.094 (4)	0.118 (5)	0.095 (4)	0.008 (3)	0.024 (3)	0.000 (3)
C20	0.076 (3)	0.073 (4)	0.094 (4)	−0.012 (3)	0.029 (3)	−0.014 (3)
C21	0.174 (6)	0.135 (6)	0.175 (6)	−0.007 (5)	0.118 (5)	−0.056 (5)
C22	0.071 (3)	0.054 (3)	0.078 (3)	0.007 (2)	0.018 (2)	0.008 (2)
C23	0.091 (3)	0.055 (3)	0.086 (3)	0.019 (3)	0.021 (3)	0.013 (2)
C24	0.106 (4)	0.051 (3)	0.071 (3)	0.003 (3)	0.020 (3)	0.006 (2)
C25	0.088 (3)	0.067 (3)	0.064 (3)	−0.011 (3)	0.011 (2)	0.006 (2)
C26	0.062 (3)	0.062 (3)	0.065 (3)	0.002 (2)	0.006 (2)	−0.005 (2)
C27	0.067 (3)	0.043 (2)	0.052 (3)	0.001 (2)	0.008 (2)	−0.0058 (18)
C28	0.057 (3)	0.050 (2)	0.059 (3)	0.003 (2)	0.006 (2)	0.000 (2)
C29	0.055 (2)	0.043 (2)	0.057 (3)	0.0051 (19)	−0.0005 (19)	−0.0004 (18)
C30	0.061 (3)	0.051 (3)	0.070 (3)	0.003 (2)	−0.008 (2)	−0.008 (2)
C31	0.059 (3)	0.073 (3)	0.114 (4)	0.000 (2)	−0.018 (3)	−0.007 (3)
C32	0.064 (3)	0.050 (2)	0.051 (3)	0.008 (2)	−0.004 (2)	−0.0042 (18)
C33	0.063 (2)	0.043 (2)	0.060 (3)	0.0038 (19)	−0.005 (2)	−0.002 (2)
C34	0.122 (4)	0.081 (3)	0.067 (4)	0.038 (3)	−0.008 (3)	0.001 (3)
C35	0.153 (5)	0.093 (4)	0.089 (4)	0.044 (4)	−0.008 (4)	0.025 (3)
C36	0.083 (4)	0.064 (4)	0.152 (6)	0.015 (3)	0.004 (4)	0.010 (4)
C37	0.085 (4)	0.071 (4)	0.119 (5)	0.011 (3)	0.023 (3)	−0.021 (3)
C38	0.076 (3)	0.061 (3)	0.078 (3)	0.012 (2)	0.008 (2)	−0.009 (2)
C39	0.057 (2)	0.046 (2)	0.079 (3)	0.002 (2)	0.002 (2)	0.013 (2)
C40	0.092 (3)	0.070 (3)	0.091 (4)	−0.006 (3)	0.017 (3)	0.016 (3)
C41	0.060 (3)	0.059 (3)	0.082 (3)	0.007 (2)	0.015 (2)	0.005 (3)
C42	0.096 (3)	0.097 (4)	0.103 (4)	−0.021 (3)	−0.026 (3)	−0.009 (3)

Geometric parameters (Å, º)

O1—C10	1.245 (5)	C16—H16	0.930
O2—C20	1.206 (5)	C17—H17	0.930
O3—C20	1.313 (6)	C18—C20	1.490 (6)
O3—C21	1.450 (6)	C18—C19	1.518 (6)
O4—C28	1.240 (4)	C18—H18	0.980
O5—C41	1.198 (5)	C19—H19A	0.960
O6—C41	1.336 (5)	C19—H19B	0.960
O6—C42	1.470 (6)	C19—H19C	0.960
N1—C10	1.373 (6)	C21—H21A	0.960
N1—N2	1.395 (5)	C21—H21B	0.960
N1—C6	1.412 (6)	C21—H21C	0.960
N2—C7	1.312 (6)	C22—C23	1.380 (6)
N3—C11	1.321 (5)	C22—C27	1.388 (5)
N3—C18	1.444 (5)	C22—H22	0.930
N3—H3	0.860	C23—C24	1.371 (6)
N4—C28	1.379 (5)	C23—H23	0.930
N4—N5	1.406 (4)	C24—C25	1.353 (6)
N4—C27	1.408 (5)	C24—H24	0.930
N5—C30	1.327 (5)	C25—C26	1.378 (6)
N6—C32	1.335 (5)	C25—H25	0.930
N6—C39	1.452 (5)	C26—C27	1.379 (5)
N6—H6	0.860	C26—H26	0.930
C1—C6	1.376 (7)	C28—C29	1.441 (5)
C1—C2	1.394 (8)	C29—C32	1.381 (5)
C1—H1	0.930	C29—C30	1.423 (5)
C2—C3	1.361 (8)	C30—C31	1.492 (6)
C2—H2	0.930	C31—H31A	0.960
C3—C4	1.344 (8)	C31—H31B	0.960
C3—H3A	0.930	C31—H31C	0.960
C4—C5	1.396 (8)	C32—C33	1.479 (5)
C4—H4	0.930	C33—C34	1.347 (6)
C5—C6	1.372 (7)	C33—C38	1.376 (6)
C5—H5	0.930	C34—C35	1.384 (7)
C7—C9	1.440 (6)	C34—H34	0.930
C7—C8	1.492 (6)	C35—C36	1.348 (8)
C8—H8A	0.960	C35—H35	0.930
C8—H8B	0.960	C36—C37	1.357 (7)
C8—H8C	0.960	C36—H36	0.930
C9—C11	1.376 (6)	C37—C38	1.389 (7)
C9—C10	1.441 (6)	C37—H37	0.930
C11—C12	1.484 (6)	C38—H38	0.930
C12—C13	1.370 (6)	C39—C41	1.497 (6)
C12—C17	1.380 (5)	C39—C40	1.539 (6)
C13—C14	1.391 (7)	C39—H39	0.980
C13—H13	0.930	C40—H40A	0.960
C14—C15	1.364 (7)	C40—H40B	0.960
C14—H14	0.930	C40—H40C	0.960
C15—C16	1.361 (7)	C42—H42A	0.960
C15—H15	0.930	C42—H42B	0.960
C16—C17	1.379 (6)	C42—H42C	0.960
C20—O3—C21	117.2 (4)	O2—C20—C18	124.6 (5)
C41—O6—C42	117.1 (4)	O3—C20—C18	111.7 (4)
C10—N1—N2	112.2 (4)	O3—C21—H21A	109.5
C10—N1—C6	128.8 (4)	O3—C21—H21B	109.5
N2—N1—C6	119.0 (4)	H21A—C21—H21B	109.5
C7—N2—N1	106.8 (4)	O3—C21—H21C	109.5
C11—N3—C18	127.8 (4)	H21A—C21—H21C	109.5
C11—N3—H3	116.1	H21B—C21—H21C	109.5
C18—N3—H3	116.1	C23—C22—C27	118.8 (4)
C28—N4—N5	112.1 (3)	C23—C22—H22	120.6
C28—N4—C27	129.1 (3)	C27—C22—H22	120.6
N5—N4—C27	118.4 (3)	C24—C23—C22	121.5 (4)
C30—N5—N4	105.9 (3)	C24—C23—H23	119.2
C32—N6—C39	127.1 (3)	C22—C23—H23	119.2
C32—N6—H6	116.5	C25—C24—C23	119.0 (4)
C39—N6—H6	116.5	C25—C24—H24	120.5
C6—C1—C2	119.9 (6)	C23—C24—H24	120.5
C6—C1—H1	120.0	C24—C25—C26	121.1 (4)
C2—C1—H1	120.0	C24—C25—H25	119.4
C3—C2—C1	120.4 (6)	C26—C25—H25	119.4
C3—C2—H2	119.8	C25—C26—C27	120.0 (4)
C1—C2—H2	119.8	C25—C26—H26	120.0
C4—C3—C2	119.4 (6)	C27—C26—H26	120.0
C4—C3—H3A	120.3	C26—C27—C22	119.4 (4)
C2—C3—H3A	120.3	C26—C27—N4	119.7 (4)
C3—C4—C5	121.7 (6)	C22—C27—N4	120.9 (4)
C3—C4—H4	119.1	O4—C28—N4	126.1 (4)
C5—C4—H4	119.1	O4—C28—C29	129.3 (4)
C6—C5—C4	119.0 (6)	N4—C28—C29	104.6 (3)
C6—C5—H5	120.5	C32—C29—C30	131.2 (4)
C4—C5—H5	120.5	C32—C29—C28	122.5 (4)
C5—C6—C1	119.5 (5)	C30—C29—C28	106.0 (3)
C5—C6—N1	121.0 (5)	N5—C30—C29	111.4 (3)
C1—C6—N1	119.5 (5)	N5—C30—C31	118.0 (4)
N2—C7—C9	111.0 (4)	C29—C30—C31	130.6 (4)
N2—C7—C8	118.9 (4)	C30—C31—H31A	109.5
C9—C7—C8	130.2 (5)	C30—C31—H31B	109.5
C7—C8—H8A	109.5	H31A—C31—H31B	109.5
C7—C8—H8B	109.5	C30—C31—H31C	109.5
H8A—C8—H8B	109.5	H31A—C31—H31C	109.5
C7—C8—H8C	109.5	H31B—C31—H31C	109.5
H8A—C8—H8C	109.5	N6—C32—C29	119.3 (3)
H8B—C8—H8C	109.5	N6—C32—C33	117.6 (4)
C11—C9—C7	131.8 (4)	C29—C32—C33	123.0 (4)
C11—C9—C10	122.7 (4)	C34—C33—C38	118.9 (4)
C7—C9—C10	105.4 (4)	C34—C33—C32	121.5 (4)
O1—C10—N1	126.6 (4)	C38—C33—C32	119.6 (4)
O1—C10—C9	128.7 (4)	C33—C34—C35	121.6 (5)
N1—C10—C9	104.7 (4)	C33—C34—H34	119.2
N3—C11—C9	119.6 (4)	C35—C34—H34	119.2
N3—C11—C12	118.5 (4)	C36—C35—C34	119.1 (6)
C9—C11—C12	121.8 (4)	C36—C35—H35	120.4
C13—C12—C17	119.6 (4)	C34—C35—H35	120.4
C13—C12—C11	121.8 (4)	C35—C36—C37	120.8 (5)
C17—C12—C11	118.6 (4)	C35—C36—H36	119.6
C12—C13—C14	119.5 (5)	C37—C36—H36	119.6
C12—C13—H13	120.3	C36—C37—C38	119.7 (5)
C14—C13—H13	120.3	C36—C37—H37	120.1
C15—C14—C13	120.2 (5)	C38—C37—H37	120.1
C15—C14—H14	119.9	C33—C38—C37	119.8 (5)
C13—C14—H14	119.9	C33—C38—H38	120.1
C16—C15—C14	120.5 (5)	C37—C38—H38	120.1
C16—C15—H15	119.7	N6—C39—C41	108.5 (3)
C14—C15—H15	119.7	N6—C39—C40	110.8 (4)
C15—C16—C17	119.6 (5)	C41—C39—C40	109.9 (3)
C15—C16—H16	120.2	N6—C39—H39	109.2
C17—C16—H16	120.2	C41—C39—H39	109.2
C16—C17—C12	120.5 (4)	C40—C39—H39	109.2
C16—C17—H17	119.8	C39—C40—H40A	109.5
C12—C17—H17	119.8	C39—C40—H40B	109.5
N3—C18—C20	108.6 (4)	H40A—C40—H40B	109.5
N3—C18—C19	112.1 (4)	C39—C40—H40C	109.5
C20—C18—C19	109.5 (4)	H40A—C40—H40C	109.5
N3—C18—H18	108.9	H40B—C40—H40C	109.5
C20—C18—H18	108.9	O5—C41—O6	123.3 (4)
C19—C18—H18	108.9	O5—C41—C39	126.0 (4)
C18—C19—H19A	109.5	O6—C41—C39	110.7 (4)
C18—C19—H19B	109.5	O6—C42—H42A	109.5
H19A—C19—H19B	109.5	O6—C42—H42B	109.5
C18—C19—H19C	109.5	H42A—C42—H42B	109.5
H19A—C19—H19C	109.5	O6—C42—H42C	109.5
H19B—C19—H19C	109.5	H42A—C42—H42C	109.5
O2—C20—O3	123.7 (4)	H42B—C42—H42C	109.5
C10—N1—N2—C7	−1.1 (5)	N3—C18—C20—O3	153.0 (4)
C6—N1—N2—C7	−177.7 (4)	C19—C18—C20—O3	−84.3 (5)
C28—N4—N5—C30	−1.8 (4)	C27—C22—C23—C24	0.4 (7)
C27—N4—N5—C30	−175.3 (4)	C22—C23—C24—C25	0.5 (7)
C6—C1—C2—C3	−0.2 (9)	C23—C24—C25—C26	−0.3 (7)
C1—C2—C3—C4	−1.3 (9)	C24—C25—C26—C27	−0.8 (6)
C2—C3—C4—C5	1.4 (9)	C25—C26—C27—C22	1.7 (6)
C3—C4—C5—C6	0.1 (9)	C25—C26—C27—N4	−178.8 (4)
C4—C5—C6—C1	−1.6 (7)	C23—C22—C27—C26	−1.4 (6)
C4—C5—C6—N1	178.4 (5)	C23—C22—C27—N4	179.1 (4)
C2—C1—C6—C5	1.7 (8)	C28—N4—C27—C26	−156.8 (4)
C2—C1—C6—N1	−178.4 (5)	N5—N4—C27—C26	15.3 (5)
C10—N1—C6—C5	7.1 (7)	C28—N4—C27—C22	22.7 (6)
N2—N1—C6—C5	−176.9 (4)	N5—N4—C27—C22	−165.1 (4)
C10—N1—C6—C1	−172.9 (5)	N5—N4—C28—O4	−176.7 (4)
N2—N1—C6—C1	3.1 (6)	C27—N4—C28—O4	−4.1 (7)
N1—N2—C7—C9	0.4 (5)	N5—N4—C28—C29	0.8 (4)
N1—N2—C7—C8	179.6 (4)	C27—N4—C28—C29	173.4 (4)
N2—C7—C9—C11	175.6 (5)	O4—C28—C29—C32	3.4 (6)
C8—C7—C9—C11	−3.5 (8)	N4—C28—C29—C32	−174.0 (4)
N2—C7—C9—C10	0.4 (5)	O4—C28—C29—C30	177.8 (4)
C8—C7—C9—C10	−178.7 (5)	N4—C28—C29—C30	0.4 (4)
N2—N1—C10—O1	−179.5 (4)	N4—N5—C30—C29	2.0 (5)
C6—N1—C10—O1	−3.3 (8)	N4—N5—C30—C31	178.7 (4)
N2—N1—C10—C9	1.3 (5)	C32—C29—C30—N5	172.2 (4)
C6—N1—C10—C9	177.5 (4)	C28—C29—C30—N5	−1.6 (5)
C11—C9—C10—O1	4.1 (8)	C32—C29—C30—C31	−3.9 (8)
C7—C9—C10—O1	179.9 (5)	C28—C29—C30—C31	−177.7 (5)
C11—C9—C10—N1	−176.8 (4)	C39—N6—C32—C29	175.3 (4)
C7—C9—C10—N1	−1.0 (5)	C39—N6—C32—C33	−3.7 (6)
C18—N3—C11—C9	−179.1 (4)	C30—C29—C32—N6	−176.3 (4)
C18—N3—C11—C12	−0.1 (7)	C28—C29—C32—N6	−3.4 (6)
C7—C9—C11—N3	−173.7 (4)	C30—C29—C32—C33	2.6 (7)
C10—C9—C11—N3	0.8 (7)	C28—C29—C32—C33	175.5 (4)
C7—C9—C11—C12	7.3 (8)	N6—C32—C33—C34	−81.3 (5)
C10—C9—C11—C12	−178.1 (4)	C29—C32—C33—C34	99.7 (6)
N3—C11—C12—C13	87.1 (5)	N6—C32—C33—C38	97.7 (5)
C9—C11—C12—C13	−93.9 (5)	C29—C32—C33—C38	−81.2 (5)
N3—C11—C12—C17	−93.2 (5)	C38—C33—C34—C35	0.3 (8)
C9—C11—C12—C17	85.8 (5)	C32—C33—C34—C35	179.3 (5)
C17—C12—C13—C14	−1.7 (7)	C33—C34—C35—C36	0.2 (9)
C11—C12—C13—C14	178.1 (4)	C34—C35—C36—C37	−0.2 (10)
C12—C13—C14—C15	−0.6 (8)	C35—C36—C37—C38	−0.2 (9)
C13—C14—C15—C16	2.4 (8)	C34—C33—C38—C37	−0.7 (6)
C14—C15—C16—C17	−1.8 (7)	C32—C33—C38—C37	−179.7 (4)
C15—C16—C17—C12	−0.5 (6)	C36—C37—C38—C33	0.7 (7)
C13—C12—C17—C16	2.3 (6)	C32—N6—C39—C41	−127.7 (4)
C11—C12—C17—C16	−177.5 (4)	C32—N6—C39—C40	111.5 (5)
C11—N3—C18—C20	−145.4 (4)	C42—O6—C41—O5	−0.1 (7)
C11—N3—C18—C19	93.5 (5)	C42—O6—C41—C39	−179.7 (4)
C21—O3—C20—O2	−1.1 (8)	N6—C39—C41—O5	−26.5 (6)
C21—O3—C20—C18	177.3 (5)	C40—C39—C41—O5	94.8 (5)
N3—C18—C20—O2	−28.6 (7)	N6—C39—C41—O6	153.2 (3)
C19—C18—C20—O2	94.1 (6)	C40—C39—C41—O6	−85.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	0.86	2.00	2.713 (5)	139
N6—H6···O4	0.86	2.01	2.715 (4)	138