Methyl 2-amino-4-(3-fluoro­phen­yl)-4H-benzo[h]chromene-3-carboxyl­ate methanol solvate

The title compound, C₂₁H₁₆FNO₃·CH₃OH, was synthesized by the reaction of 1-naphthol with methyl cyano­acetate and 3-fluoro­benzaldehyde in methanol under microwave irradiation. The pyran rings of the two independent mol­ecules in the asymmetric unit adopt boat conformations. The crystal packing is stabilized by inter­molecular N—H...O, O—H...O and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.065
• wR factor = 0.193
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)        3000 Deg.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

Alert level G
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
   4 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL.

Methyl 2-amino-4-(3-fluorophenyl)-4H-benzo[h]chromene-3-carboxylate methanol solvate

Crystal data

C21H16FNO3·CH4O	Z = 4
Mr = 381.39	F(000) = 800
Triclinic, P1	Dx = 1.290 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.225 (2) Å	Cell parameters from 25 reflections
b = 11.375 (2) Å	θ = 10–12°
c = 17.283 (4) Å	µ = 0.10 mm^−1
α = 76.26 (3)°	T = 293 K
β = 71.80 (3)°	Block, colourless
γ = 71.50 (3)°	0.40 × 0.30 × 0.30 mm
V = 1964.4 (8) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	4171 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 26.0°, θmin = 1.3°
ω/2θ scans	h = −12→13
Absorption correction: ψ scan (North et al., 1968)	k = −13→14
Tmin = 0.962, Tmax = 0.972	l = 0→21
7688 measured reflections	3 standard reflections every 200 reflections
7688 independent reflections	intensity decay: none

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.193	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
7688 reflections	(Δ/σ)max = 0.001
506 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

Experimental. ¹H NMR (CDCl₃): δ 7.95 (d, 1H),7.77(d, 2H), 7.43 (d, 2H), 7.29 (m, 1H), 7.09 (d, 2H), 6.99 (m, 1H), 6.75 (m, 1H), 6.30 (m, 1H), 5.60 (s, 1H), 3.73(s, 3H).

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
F1	−0.2564 (6)	0.4151 (5)	0.3817 (4)	0.149 (2)
O1	0.2548 (3)	−0.0661 (3)	0.16499 (17)	0.0652 (10)
O2	−0.0570 (3)	−0.0254 (3)	0.09241 (17)	0.1087 (18)
O3	−0.1881 (3)	0.0810 (4)	0.1963 (2)	0.0651 (10)
O4	0.4695 (4)	0.7903 (5)	0.9942 (3)	0.1108 (18)
H4B	0.4861	0.7166	1.0157	0.166*
N1	0.1966 (4)	−0.0615 (5)	0.0592 (3)	0.0714 (13)
H1A	0.2782	−0.0867	0.0362	0.086*
H1B	0.1405	−0.0490	0.0317	0.086*
C1	0.0407 (2)	0.3724 (4)	0.2171 (3)	0.106 (3)
H1C	0.0964	0.4188	0.1813	0.128*
C2	−0.0682 (2)	0.4288 (4)	0.2751 (3)	0.107 (3)
H2A	−0.0861	0.5132	0.2786	0.128*
C3	−0.1454 (3)	0.3596 (4)	0.3249 (3)	0.091 (2)
C4	−0.1250 (2)	0.2379 (3)	0.3226 (3)	0.0669 (15)
H4A	−0.1826	0.1935	0.3584	0.080*
C5	−0.0173 (2)	0.1786 (2)	0.2664 (3)	0.0527 (12)
C6	0.0646 (2)	0.2462 (3)	0.2136 (3)	0.0761 (17)
H6A	0.1366	0.2075	0.1752	0.091*
C7	0.0103 (2)	0.0371 (2)	0.2663 (3)	0.0469 (10)
H7A	−0.0667	0.0106	0.3017	0.056*
C8	0.0333 (2)	0.0065 (2)	0.1816 (3)	0.0507 (11)
C9	0.1575 (3)	−0.0423 (2)	0.1364 (3)	0.0487 (11)
C10	0.2407 (3)	−0.0880 (2)	0.2535 (3)	0.0507 (11)
C11	0.3485 (3)	−0.1572 (2)	0.2845 (3)	0.0583 (13)
C12	0.4708 (4)	−0.2120 (2)	0.2337 (3)	0.0727 (16)
H12A	0.4823	−0.2004	0.1770	0.087*
C13	0.5734 (4)	−0.2827 (3)	0.2674 (3)	0.088 (2)
H13A	0.6537	−0.3175	0.2336	0.106*
C14	0.5544 (4)	−0.3011 (3)	0.3532 (3)	0.089 (2)
H14A	0.6230	−0.3482	0.3762	0.106*
C15	0.4384 (4)	−0.2513 (2)	0.4026 (3)	0.0820 (18)
H15A	0.4279	−0.2670	0.4594	0.098*
C16	0.3327 (4)	−0.1765 (2)	0.3710 (3)	0.0624 (14)
C17	0.2104 (3)	−0.1223 (2)	0.4209 (4)	0.0767 (16)
H17A	0.1990	−0.1334	0.4776	0.092*
C18	0.1108 (2)	−0.0555 (2)	0.3893 (3)	0.0626 (13)
H18A	0.0320	−0.0212	0.4246	0.075*
C19	0.1209 (3)	−0.0347 (2)	0.3023 (3)	0.0489 (11)
C20	−0.0746 (2)	0.0270 (2)	0.1482 (3)	0.0531 (12)
C21	−0.3012 (4)	0.1015 (3)	0.1676 (2)	0.086 (2)
H21A	−0.3771	0.1415	0.2062	0.130*
H21B	−0.3096	0.0225	0.1624	0.130*
H21C	−0.2925	0.1542	0.1149	0.130*
C22	0.5776 (5)	0.8160 (5)	0.9426 (6)	0.182 (6)
H22A	0.5583	0.9023	0.9173	0.273*
H22B	0.6110	0.7630	0.9007	0.273*
H22C	0.6414	0.8011	0.9725	0.273*
F2	0.6167 (4)	0.0926 (3)	0.4294 (3)	0.1062 (14)
O5	0.1703 (3)	0.6173 (3)	0.2181 (2)	0.0580 (9)
O6	0.5473 (3)	0.5256 (4)	0.0651 (2)	0.0743 (11)
O7	0.6211 (3)	0.4393 (3)	0.1777 (2)	0.0627 (10)
O8	1.0305 (5)	0.7351 (5)	0.0521 (4)	0.1151 (19)
H8A	1.0062	0.8076	0.0613	0.173*
N2	0.2812 (4)	0.5989 (5)	0.0906 (3)	0.0695 (13)
H2B	0.2069	0.6336	0.0798	0.083*
H2C	0.3496	0.5784	0.0513	0.083*
C23	0.4574 (7)	0.0844 (5)	0.3717 (4)	0.0741 (16)
H23A	0.4720	−0.0014	0.3906	0.089*
C24	0.5255 (4)	0.1515 (3)	0.3864 (4)	0.0628 (14)
C25	0.5053 (4)	0.2797 (3)	0.3599 (3)	0.0570 (12)
H25A	0.5537	0.3232	0.3715	0.068*
C26	0.4142 (4)	0.3418 (3)	0.3170 (3)	0.0476 (11)
C27	0.3439 (3)	0.2736 (2)	0.3012 (3)	0.0583 (12)
H27A	0.2814	0.3147	0.2721	0.070*
C28	0.3646 (4)	0.1466 (2)	0.3277 (3)	0.0704 (15)
H28A	0.3167	0.1024	0.3162	0.084*
C29	0.3871 (4)	0.4827 (4)	0.2892 (3)	0.0483 (11)
H29A	0.4520	0.5111	0.3016	0.058*
C30	0.3985 (4)	0.5207 (4)	0.1973 (3)	0.0501 (11)
C31	0.2905 (4)	0.5768 (4)	0.1682 (3)	0.0508 (11)
C32	0.1560 (3)	0.6115 (4)	0.3020 (3)	0.0509 (11)
C33	0.0296 (2)	0.6755 (4)	0.3443 (3)	0.0581 (13)
C34	−0.0692 (2)	0.7446 (5)	0.3058 (4)	0.0678 (15)
H34A	−0.0551	0.7485	0.2494	0.081*
C35	−0.1865 (3)	0.8066 (6)	0.3508 (4)	0.086 (2)
H35A	−0.2509	0.8532	0.3242	0.103*
C36	−0.2121 (7)	0.8018 (6)	0.4358 (6)	0.103 (3)
H36A	−0.2927	0.8439	0.4657	0.123*
C37	−0.1189 (3)	0.7357 (7)	0.4733 (5)	0.099 (3)
H37A	−0.1366	0.7323	0.5300	0.118*
C38	0.0067 (2)	0.6701 (5)	0.4308 (4)	0.0726 (17)
C39	0.1084 (2)	0.6014 (6)	0.4686 (4)	0.0822 (19)
H39A	0.0935	0.5958	0.5252	0.099*
C40	0.2269 (3)	0.5435 (5)	0.4245 (3)	0.0659 (14)
H40A	0.2918	0.4994	0.4513	0.079*
C41	0.2538 (3)	0.5488 (4)	0.3385 (3)	0.0525 (12)
C42	0.5226 (4)	0.4960 (5)	0.1404 (3)	0.0518 (11)
C43	0.7488 (5)	0.4164 (6)	0.1246 (3)	0.087 (2)
H43A	0.8108	0.3764	0.1567	0.130*
H43B	0.7652	0.4945	0.0941	0.130*
H43C	0.7566	0.3628	0.0869	0.130*
C44	0.9358 (8)	0.7060 (7)	0.0402 (2)	0.144 (4)
H44A	0.9642	0.6210	0.0295	0.217*
H44B	0.9088	0.7614	−0.0061	0.217*
H44C	0.8641	0.7138	0.0885	0.217*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.120 (5)	0.107 (3)	0.141 (5)	0.042 (3)	−0.061 (4)	−0.081 (3)
O1	0.042 (2)	0.056 (3)	0.059 (2)	−0.0116 (18)	−0.0184 (17)	−0.0118 (18)
O2	0.077 (3)	0.115 (5)	0.080 (3)	−0.039 (3)	0.002 (2)	−0.054 (3)
O3	0.0463 (19)	0.089 (3)	0.060 (2)	−0.0076 (18)	−0.0133 (16)	−0.0269 (19)
O4	0.070 (3)	0.091 (3)	0.119 (4)	0.000 (2)	0.011 (3)	0.004 (3)
N1	0.050 (2)	0.109 (4)	0.056 (3)	−0.012 (2)	−0.010 (2)	−0.029 (2)
C1	0.097 (5)	0.072 (4)	0.180 (8)	−0.035 (4)	−0.083 (6)	0.006 (5)
C2	0.122 (6)	0.046 (3)	0.188 (9)	0.007 (4)	−0.108 (7)	−0.031 (5)
C3	0.100 (5)	0.066 (4)	0.120 (6)	0.020 (4)	−0.067 (5)	−0.046 (4)
C4	0.067 (3)	0.068 (3)	0.066 (3)	0.003 (3)	−0.031 (3)	−0.020 (3)
C5	0.050 (3)	0.052 (3)	0.063 (3)	−0.008 (2)	−0.025 (2)	−0.015 (2)
C6	0.061 (3)	0.058 (3)	0.113 (5)	−0.019 (3)	−0.036 (3)	0.003 (3)
C7	0.045 (2)	0.046 (2)	0.047 (2)	−0.013 (2)	−0.008 (2)	−0.0075 (19)
C8	0.049 (3)	0.050 (3)	0.055 (3)	−0.017 (2)	−0.009 (2)	−0.011 (2)
C9	0.043 (2)	0.060 (3)	0.048 (3)	−0.012 (2)	−0.018 (2)	−0.010 (2)
C10	0.054 (3)	0.046 (2)	0.057 (3)	−0.016 (2)	−0.018 (2)	−0.008 (2)
C11	0.064 (3)	0.041 (2)	0.078 (4)	−0.016 (2)	−0.027 (3)	−0.009 (2)
C12	0.059 (3)	0.067 (3)	0.098 (4)	−0.008 (3)	−0.028 (3)	−0.026 (3)
C13	0.069 (4)	0.071 (4)	0.135 (6)	0.002 (3)	−0.044 (4)	−0.037 (4)
C14	0.090 (5)	0.063 (4)	0.128 (6)	−0.006 (3)	−0.072 (5)	−0.005 (4)
C15	0.101 (5)	0.056 (3)	0.101 (5)	−0.017 (3)	−0.060 (4)	0.006 (3)
C16	0.078 (4)	0.040 (3)	0.077 (4)	−0.015 (2)	−0.042 (3)	0.003 (2)
C17	0.096 (5)	0.071 (4)	0.061 (3)	−0.020 (3)	−0.027 (3)	0.001 (3)
C18	0.070 (3)	0.068 (3)	0.049 (3)	−0.017 (3)	−0.020 (3)	−0.003 (2)
C19	0.058 (3)	0.043 (2)	0.050 (3)	−0.019 (2)	−0.016 (2)	−0.0045 (19)
C20	0.048 (3)	0.065 (3)	0.044 (2)	−0.008 (2)	−0.010 (2)	−0.015 (2)
C21	0.047 (3)	0.129 (6)	0.082 (4)	−0.004 (3)	−0.020 (3)	−0.036 (4)
C22	0.089 (6)	0.217 (13)	0.194 (12)	−0.062 (7)	−0.005 (7)	0.040 (10)
F2	0.107 (4)	0.072 (2)	0.107 (3)	−0.003 (2)	−0.070 (3)	0.010 (2)
O5	0.0443 (18)	0.068 (2)	0.0507 (19)	−0.0036 (15)	−0.0076 (15)	−0.0115 (16)
O6	0.051 (2)	0.104 (3)	0.050 (2)	−0.003 (2)	−0.0114 (16)	−0.0031 (19)
O7	0.0445 (18)	0.082 (2)	0.055 (2)	−0.0110 (17)	−0.0171 (16)	−0.0013 (17)
O8	0.093 (3)	0.092 (3)	0.177 (6)	−0.004 (3)	−0.078 (4)	−0.023 (3)
N2	0.047 (2)	0.098 (3)	0.050 (2)	0.002 (2)	−0.0152 (19)	−0.011 (2)
C23	0.097 (4)	0.047 (3)	0.065 (3)	−0.015 (3)	−0.010 (3)	−0.003 (2)
C24	0.074 (3)	0.053 (3)	0.053 (3)	−0.002 (3)	−0.025 (3)	−0.001 (2)
C25	0.067 (3)	0.057 (3)	0.049 (3)	−0.016 (2)	−0.020 (2)	−0.005 (2)
C26	0.050 (3)	0.047 (2)	0.040 (2)	−0.014 (2)	−0.002 (2)	−0.0060 (18)
C27	0.057 (3)	0.052 (3)	0.068 (3)	−0.016 (2)	−0.018 (3)	−0.010 (2)
C28	0.071 (4)	0.059 (3)	0.081 (4)	−0.023 (3)	−0.009 (3)	−0.017 (3)
C29	0.050 (3)	0.051 (3)	0.046 (2)	−0.015 (2)	−0.015 (2)	−0.0049 (19)
C30	0.049 (3)	0.048 (2)	0.049 (3)	−0.012 (2)	−0.010 (2)	−0.005 (2)
C31	0.047 (3)	0.048 (3)	0.053 (3)	−0.010 (2)	−0.011 (2)	−0.004 (2)
C32	0.051 (3)	0.044 (2)	0.058 (3)	−0.018 (2)	−0.006 (2)	−0.013 (2)
C33	0.057 (3)	0.038 (2)	0.070 (3)	−0.016 (2)	0.003 (3)	−0.014 (2)
C34	0.053 (3)	0.047 (3)	0.089 (4)	−0.011 (2)	0.000 (3)	−0.013 (3)
C35	0.064 (4)	0.059 (3)	0.107 (5)	−0.014 (3)	0.009 (4)	−0.008 (3)
C36	0.071 (4)	0.062 (4)	0.128 (7)	0.000 (3)	0.027 (4)	−0.021 (4)
C37	0.104 (5)	0.073 (4)	0.085 (5)	−0.027 (4)	0.040 (4)	−0.030 (4)
C38	0.082 (4)	0.047 (3)	0.070 (4)	−0.014 (3)	0.010 (3)	−0.018 (3)
C39	0.110 (5)	0.072 (4)	0.055 (3)	−0.027 (4)	0.005 (3)	−0.023 (3)
C40	0.080 (4)	0.058 (3)	0.056 (3)	−0.019 (3)	−0.011 (3)	−0.011 (2)
C41	0.063 (3)	0.044 (2)	0.052 (3)	−0.022 (2)	−0.005 (2)	−0.012 (2)
C42	0.043 (2)	0.061 (3)	0.048 (3)	−0.011 (2)	−0.012 (2)	−0.005 (2)
C43	0.044 (3)	0.122 (6)	0.078 (4)	−0.014 (3)	−0.013 (3)	−0.002 (4)
C44	0.129 (8)	0.126 (8)	0.202 (11)	−0.048 (6)	−0.064 (8)	−0.021 (7)

Geometric parameters (Å, º)

F1—C3	1.395 (9)	F2—C24	1.362 (6)
O1—C9	1.264 (5)	O5—C31	1.358 (5)
O1—C10	1.456 (5)	O5—C32	1.396 (6)
O2—C20	1.185 (5)	O6—C42	1.227 (6)
O3—C20	1.333 (5)	O7—C42	1.361 (5)
O3—C21	1.436 (6)	O7—C43	1.422 (6)
O4—C22	1.333 (9)	O8—C44	1.294 (10)
O4—H4B	0.82	O8—H8A	0.82
N1—C9	1.318 (6)	N2—C31	1.336 (6)
N1—H1A	0.86	N2—H2B	0.86
N1—H1B	0.86	N2—H2C	0.86
C1—C6	1.387 (9)	C23—C24	1.348 (8)
C1—C2	1.398 (12)	C23—C28	1.391 (8)
C1—H1C	0.93	C23—H23A	0.93
C2—C3	1.325 (11)	C24—C25	1.387 (7)
C2—H2A	0.93	C25—C26	1.364 (7)
C3—C4	1.338 (9)	C25—H25A	0.93
C4—C5	1.385 (7)	C26—C27	1.386 (7)
C4—H4A	0.93	C26—C29	1.520 (6)
C5—C6	1.364 (8)	C27—C28	1.375 (7)
C5—C7	1.540 (6)	C27—H27A	0.93
C6—H6A	0.93	C28—H28A	0.93
C7—C19	1.481 (6)	C29—C30	1.518 (6)
C7—C8	1.510 (6)	C29—C41	1.524 (7)
C7—H7A	0.98	C29—H29A	0.98
C8—C9	1.376 (6)	C30—C31	1.367 (6)
C8—C20	1.431 (7)	C30—C42	1.420 (6)
C10—C19	1.380 (7)	C32—C41	1.354 (7)
C10—C11	1.404 (7)	C32—C33	1.424 (7)
C11—C12	1.418 (8)	C33—C34	1.396 (8)
C11—C16	1.420 (8)	C33—C38	1.425 (8)
C12—C13	1.386 (8)	C34—C35	1.367 (8)
C12—H12A	0.93	C34—H34A	0.93
C13—C14	1.405 (10)	C35—C36	1.397 (11)
C13—H13A	0.93	C35—H35A	0.93
C14—C15	1.347 (10)	C36—C37	1.331 (11)
C14—H14A	0.93	C36—H36A	0.93
C15—C16	1.405 (8)	C37—C38	1.424 (9)
C15—H15A	0.93	C37—H37A	0.93
C16—C17	1.409 (8)	C38—C39	1.413 (9)
C17—C18	1.331 (8)	C39—C40	1.355 (8)
C17—H17A	0.93	C39—H39A	0.93
C18—C19	1.438 (7)	C40—C41	1.413 (7)
C18—H18A	0.93	C40—H40A	0.93
C21—H21A	0.96	C43—H43A	0.96
C21—H21B	0.96	C43—H43B	0.96
C21—H21C	0.96	C43—H43C	0.96
C22—H22A	0.96	C44—H44A	0.96
C22—H22B	0.96	C44—H44B	0.96
C22—H22C	0.96	C44—H44C	0.96
C9—O1—C10	120.9 (3)	C31—O5—C32	119.4 (4)
C20—O3—C21	116.3 (4)	C42—O7—C43	116.0 (4)
C22—O4—H4B	109.5	C44—O8—H8A	109.5
C9—N1—H1A	120.0	C31—N2—H2B	120.0
C9—N1—H1B	120.0	C31—N2—H2C	120.0
H1A—N1—H1B	120.0	H2B—N2—H2C	120.0
C6—C1—C2	119.0 (7)	C24—C23—C28	118.3 (5)
C6—C1—H1C	120.5	C24—C23—H23A	120.9
C2—C1—H1C	120.5	C28—C23—H23A	120.9
C3—C2—C1	118.8 (6)	C23—C24—F2	119.3 (5)
C3—C2—H2A	120.6	C23—C24—C25	122.4 (5)
C1—C2—H2A	120.6	F2—C24—C25	118.3 (5)
C2—C3—C4	123.4 (7)	C26—C25—C24	119.8 (5)
C2—C3—F1	119.5 (7)	C26—C25—H25A	120.1
C4—C3—F1	117.1 (8)	C24—C25—H25A	120.1
C3—C4—C5	119.4 (7)	C25—C26—C27	118.3 (4)
C3—C4—H4A	120.3	C25—C26—C29	121.1 (4)
C5—C4—H4A	120.3	C27—C26—C29	120.5 (4)
C6—C5—C4	119.2 (5)	C28—C27—C26	121.5 (5)
C6—C5—C7	121.1 (5)	C28—C27—H27A	119.3
C4—C5—C7	119.7 (5)	C26—C27—H27A	119.3
C5—C6—C1	120.1 (7)	C27—C28—C23	119.7 (5)
C5—C6—H6A	119.9	C27—C28—H28A	120.1
C1—C6—H6A	119.9	C23—C28—H28A	120.1
C19—C7—C8	110.9 (4)	C30—C29—C26	113.4 (4)
C19—C7—C5	110.7 (4)	C30—C29—C41	110.5 (4)
C8—C7—C5	112.6 (4)	C26—C29—C41	110.2 (4)
C19—C7—H7A	107.5	C30—C29—H29A	107.5
C8—C7—H7A	107.5	C26—C29—H29A	107.5
C5—C7—H7A	107.5	C41—C29—H29A	107.5
C9—C8—C20	119.6 (4)	C31—C30—C42	119.1 (4)
C9—C8—C7	120.5 (4)	C31—C30—C29	121.0 (4)
C20—C8—C7	119.9 (4)	C42—C30—C29	119.9 (4)
O1—C9—N1	109.7 (4)	N2—C31—O5	108.7 (4)
O1—C9—C8	121.6 (4)	N2—C31—C30	128.4 (4)
N1—C9—C8	128.5 (4)	O5—C31—C30	122.8 (4)
C19—C10—C11	123.5 (5)	C41—C32—O5	122.3 (4)
C19—C10—O1	117.2 (4)	C41—C32—C33	124.2 (5)
C11—C10—O1	119.3 (4)	O5—C32—C33	113.5 (4)
C10—C11—C12	122.9 (5)	C34—C33—C32	124.0 (5)
C10—C11—C16	118.4 (5)	C34—C33—C38	119.4 (5)
C12—C11—C16	118.7 (5)	C32—C33—C38	116.6 (5)
C13—C12—C11	120.9 (6)	C35—C34—C33	120.1 (6)
C13—C12—H12A	119.6	C35—C34—H34A	119.9
C11—C12—H12A	119.6	C33—C34—H34A	119.9
C14—C13—C12	119.1 (6)	C34—C35—C36	121.7 (7)
C14—C13—H13A	120.4	C34—C35—H35A	119.2
C12—C13—H13A	120.4	C36—C35—H35A	119.2
C15—C14—C13	120.8 (6)	C37—C36—C35	118.7 (6)
C15—C14—H14A	119.6	C37—C36—H36A	120.6
C13—C14—H14A	119.6	C35—C36—H36A	120.6
C14—C15—C16	121.9 (7)	C36—C37—C38	123.2 (7)
C14—C15—H15A	119.0	C36—C37—H37A	118.4
C16—C15—H15A	119.0	C38—C37—H37A	118.4
C15—C16—C17	123.3 (6)	C39—C38—C37	124.4 (6)
C15—C16—C11	118.5 (6)	C39—C38—C33	118.7 (5)
C17—C16—C11	118.1 (5)	C37—C38—C33	116.9 (7)
C18—C17—C16	121.9 (5)	C40—C39—C38	121.7 (6)
C18—C17—H17A	119.1	C40—C39—H39A	119.1
C16—C17—H17A	119.1	C38—C39—H39A	119.1
C17—C18—C19	122.3 (5)	C39—C40—C41	121.1 (6)
C17—C18—H18A	118.9	C39—C40—H40A	119.4
C19—C18—H18A	118.9	C41—C40—H40A	119.4
C10—C19—C18	115.8 (5)	C32—C41—C40	117.6 (5)
C10—C19—C7	121.2 (4)	C32—C41—C29	121.4 (4)
C18—C19—C7	123.0 (4)	C40—C41—C29	120.9 (5)
O2—C20—O3	127.6 (4)	O6—C42—O7	119.8 (4)
O2—C20—C8	117.4 (4)	O6—C42—C30	127.2 (4)
O3—C20—C8	113.3 (4)	O7—C42—C30	112.9 (4)
O3—C21—H21A	109.5	O7—C43—H43A	109.5
O3—C21—H21B	109.5	O7—C43—H43B	109.5
H21A—C21—H21B	109.5	H43A—C43—H43B	109.5
O3—C21—H21C	109.5	O7—C43—H43C	109.5
H21A—C21—H21C	109.5	H43A—C43—H43C	109.5
H21B—C21—H21C	109.5	H43B—C43—H43C	109.5
O4—C22—H22A	109.5	O8—C44—H44A	109.5
O4—C22—H22B	109.5	O8—C44—H44B	109.5
H22A—C22—H22B	109.5	H44A—C44—H44B	109.5
O4—C22—H22C	109.5	O8—C44—H44C	109.5
H22A—C22—H22C	109.5	H44A—C44—H44C	109.5
H22B—C22—H22C	109.5	H44B—C44—H44C	109.5
C6—C1—C2—C3	−0.1 (10)	C28—C23—C24—F2	179.9 (5)
C1—C2—C3—C4	−0.3 (11)	C28—C23—C24—C25	0.7 (8)
C1—C2—C3—F1	−178.3 (6)	C23—C24—C25—C26	−0.5 (8)
C2—C3—C4—C5	0.9 (9)	F2—C24—C25—C26	−179.7 (5)
F1—C3—C4—C5	179.0 (5)	C24—C25—C26—C27	0.1 (7)
C3—C4—C5—C6	−1.1 (8)	C24—C25—C26—C29	178.3 (4)
C3—C4—C5—C7	177.0 (5)	C25—C26—C27—C28	−0.1 (7)
C4—C5—C6—C1	0.8 (8)	C29—C26—C27—C28	−178.3 (5)
C7—C5—C6—C1	−177.3 (5)	C26—C27—C28—C23	0.4 (8)
C2—C1—C6—C5	−0.2 (10)	C24—C23—C28—C27	−0.6 (8)
C6—C5—C7—C19	72.3 (6)	C25—C26—C29—C30	125.8 (5)
C4—C5—C7—C19	−105.9 (5)	C27—C26—C29—C30	−56.1 (6)
C6—C5—C7—C8	−52.5 (6)	C25—C26—C29—C41	−109.7 (5)
C4—C5—C7—C8	129.4 (5)	C27—C26—C29—C41	68.4 (5)
C19—C7—C8—C9	−22.0 (6)	C26—C29—C30—C31	107.7 (5)
C5—C7—C8—C9	102.7 (5)	C41—C29—C30—C31	−16.7 (6)
C19—C7—C8—C20	157.3 (4)	C26—C29—C30—C42	−71.3 (6)
C5—C7—C8—C20	−78.0 (5)	C41—C29—C30—C42	164.4 (4)
C10—O1—C9—N1	−162.1 (4)	C32—O5—C31—N2	−176.1 (4)
C10—O1—C9—C8	22.9 (7)	C32—O5—C31—C30	5.4 (7)
C20—C8—C9—O1	−177.3 (4)	C42—C30—C31—N2	9.9 (8)
C7—C8—C9—O1	2.0 (7)	C29—C30—C31—N2	−169.1 (5)
C20—C8—C9—N1	8.7 (8)	C42—C30—C31—O5	−171.9 (4)
C7—C8—C9—N1	−171.9 (5)	C29—C30—C31—O5	9.2 (7)
C9—O1—C10—C19	−25.4 (6)	C31—O5—C32—C41	−10.8 (6)
C9—O1—C10—C11	156.8 (4)	C31—O5—C32—C33	170.2 (4)
C19—C10—C11—C12	179.6 (5)	C41—C32—C33—C34	177.1 (5)
O1—C10—C11—C12	−2.7 (7)	O5—C32—C33—C34	−3.9 (7)
C19—C10—C11—C16	1.9 (7)	C41—C32—C33—C38	−0.9 (7)
O1—C10—C11—C16	179.5 (4)	O5—C32—C33—C38	178.1 (4)
C10—C11—C12—C13	−178.1 (5)	C32—C33—C34—C35	−177.8 (5)
C16—C11—C12—C13	−0.3 (8)	C38—C33—C34—C35	0.1 (8)
C11—C12—C13—C14	0.8 (9)	C33—C34—C35—C36	−0.9 (9)
C12—C13—C14—C15	0.2 (10)	C34—C35—C36—C37	0.6 (10)
C13—C14—C15—C16	−1.8 (10)	C35—C36—C37—C38	0.5 (11)
C14—C15—C16—C17	−179.4 (6)	C36—C37—C38—C39	178.6 (7)
C14—C15—C16—C11	2.3 (9)	C36—C37—C38—C33	−1.2 (10)
C10—C11—C16—C15	176.7 (5)	C34—C33—C38—C39	−179.0 (5)
C12—C11—C16—C15	−1.2 (7)	C32—C33—C38—C39	−0.9 (7)
C10—C11—C16—C17	−1.7 (7)	C34—C33—C38—C37	0.9 (8)
C12—C11—C16—C17	−179.6 (5)	C32—C33—C38—C37	178.9 (5)
C15—C16—C17—C18	−177.6 (5)	C37—C38—C39—C40	−178.3 (6)
C11—C16—C17—C18	0.7 (9)	C33—C38—C39—C40	1.5 (9)
C16—C17—C18—C19	0.2 (9)	C38—C39—C40—C41	−0.3 (9)
C11—C10—C19—C18	−0.9 (7)	O5—C32—C41—C40	−176.8 (4)
O1—C10—C19—C18	−178.6 (4)	C33—C32—C41—C40	2.1 (7)
C11—C10—C19—C7	−179.8 (4)	O5—C32—C41—C29	1.3 (7)
O1—C10—C19—C7	2.5 (6)	C33—C32—C41—C29	−179.8 (4)
C17—C18—C19—C10	−0.2 (7)	C39—C40—C41—C32	−1.4 (8)
C17—C18—C19—C7	178.7 (5)	C39—C40—C41—C29	−179.6 (5)
C8—C7—C19—C10	18.6 (6)	C30—C29—C41—C32	11.6 (6)
C5—C7—C19—C10	−107.1 (5)	C26—C29—C41—C32	−114.6 (5)
C8—C7—C19—C18	−160.2 (4)	C30—C29—C41—C40	−170.3 (4)
C5—C7—C19—C18	74.1 (6)	C26—C29—C41—C40	63.5 (6)
C21—O3—C20—O2	−14.2 (8)	C43—O7—C42—O6	−1.0 (8)
C21—O3—C20—C8	−178.5 (5)	C43—O7—C42—C30	−177.5 (5)
C9—C8—C20—O2	17.5 (7)	C31—C30—C42—O6	4.2 (8)
C7—C8—C20—O2	−161.8 (4)	C29—C30—C42—O6	−176.8 (5)
C9—C8—C20—O3	−176.5 (4)	C31—C30—C42—O7	−179.6 (4)
C7—C8—C20—O3	4.2 (6)	C29—C30—C42—O7	−0.7 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2C···O6	0.86	2.18	2.754 (6)	124
N1—H1B···O2	0.86	2.10	2.636 (5)	120
N1—H1A···O4^i	0.86	2.17	2.993 (6)	161
O4—H4B···O6^ii	0.82	2.11	2.929 (6)	175
N1—H1B···O2^iii	0.86	2.47	3.263 (6)	154
N2—H2B···O8^iv	0.86	2.09	2.945 (8)	174
N2—H2C···O6^v	0.86	2.37	3.130 (6)	148
O8—H8A···O2^vi	0.82	1.95	2.766 (6)	175
C21—H21A···Cg1^iv	0.96	2.73	3.671 (4)	166
C28—H28A···Cg2	0.93	2.76	3.616 (4)	153
C43—H43A···Cg3^vii	0.96	2.76	3.705 (6)	167

Symmetry codes: (i) x, y−1, z−1; (ii) x, y, z+1; (iii) −x, −y, −z; (iv) x−1, y, z; (v) −x+1, −y+1, −z; (vi) x+1, y+1, z; (vii) x+1, y, z.