Crystal structure and Hirshfeld surface analysis of isopropyl 4-[2-fluoro-5-(tri­fluoro­meth­yl)phen­yl]-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate

In the crystal, an infinite chain along the a-axis direction with a C(6) chain motif is formed by N—H...O hydrogen bonds. C—H...O and C—H...F inter­actions connect these chains, generating a three-dimensional network. In addition, C—H...π inter­actions connect the mol­ecules into layers parallel to the (100) plane.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.046
• wR factor = 0.129
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
            identifier.
            yellowish
CRYSC01_ALERT_1_C No recognised colour has been given for crystal colour.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -2.080 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          7 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          6 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          4 Report
PLAT177_ALERT_4_G The CIF-Embedded .res File Contains DELU Records          1 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT230_ALERT_2_G Hirshfeld Test Diff for    F2       --C23      .        7.2 s.u.
PLAT230_ALERT_2_G Hirshfeld Test Diff for    F4       --C23      .       12.1 s.u.
PLAT230_ALERT_2_G Hirshfeld Test Diff for    F2A      --C23      .        7.2 s.u.
PLAT242_ALERT_2_G Low    'MainMol' Ueq as Compared to Neighbors of        C23 Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        10% Note
PLAT432_ALERT_2_G Short Inter X...Y Contact  F4A      ..C16      .       2.96 Ang.
                                                -1+x,y,-1+z  =      1_454 Check
PLAT480_ALERT_4_G Long H...A H-Bond Reported H2A      ..F3       .       2.59 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H12B     ..F1       .       2.64 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H12B     ..O1       .       2.65 Ang.
PLAT793_ALERT_4_G Model has Chirality at C7          (Centro SPGR)          S Verify
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          2 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         48 Note
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        4.2 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         15 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  22 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   9 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX3 (Bruker, 2018); cell refinement: SAINT (Bruker, 2018); data reduction: SAINT (Bruker, 2018); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).

Propan-2-yl 4-[2-fluoro-5-(trifluoromethyl)phenyl]-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

Crystal data

C23H25F4NO3	F(000) = 920
Mr = 439.44	Dx = 1.383 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.4918 (3) Å	Cell parameters from 8405 reflections
b = 27.8140 (11) Å	θ = 2.5–28.2°
c = 10.2023 (4) Å	µ = 0.11 mm^−1
β = 97.053 (2)°	T = 100 K
V = 2109.84 (14) Å^3	Prism, yellowish
Z = 4	0.23 × 0.17 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer	3801 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.056
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θmax = 28.3°, θmin = 2.5°
Tmin = 0.663, Tmax = 0.746	h = −9→9
21749 measured reflections	k = −36→36
5221 independent reflections	l = −13→13

Refinement

Refinement on F^2	48 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.129	w = 1/[σ^2(Fo^2) + (0.044P)^2 + 1.2617P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
5221 reflections	Δρmax = 0.35 e Å^−3
318 parameters	Δρmin = −0.37 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
F1	0.83123 (14)	0.59076 (4)	0.35900 (11)	0.0285 (3)
F2	0.0433 (2)	0.58544 (9)	0.09930 (16)	0.0425 (7)	0.763 (5)
F3	0.1611 (9)	0.62597 (14)	−0.0465 (4)	0.0398 (9)	0.763 (5)
F4	0.1702 (3)	0.54913 (6)	−0.04875 (18)	0.0370 (5)	0.763 (5)
F2A	0.0323 (7)	0.6241 (3)	0.0914 (6)	0.056 (2)	0.237 (5)
F3A	0.167 (3)	0.6171 (5)	−0.0756 (14)	0.049 (4)	0.237 (5)
F4A	0.0756 (10)	0.5551 (2)	0.0171 (8)	0.059 (3)	0.237 (5)
O1	0.81859 (16)	0.71304 (4)	0.41408 (13)	0.0227 (3)
O2	0.38263 (18)	0.57179 (5)	0.71526 (13)	0.0288 (3)
O3	0.60880 (16)	0.56439 (4)	0.58997 (12)	0.0199 (3)
N1	0.20965 (19)	0.69030 (5)	0.46495 (15)	0.0207 (3)
H1N	0.099 (3)	0.7016 (8)	0.459 (2)	0.031 (6)*
C1	0.3454 (2)	0.71772 (6)	0.42567 (16)	0.0190 (3)
C2	0.2984 (2)	0.76895 (6)	0.3917 (2)	0.0255 (4)
H2A	0.285175	0.786980	0.473603	0.031*
H2B	0.181746	0.770062	0.334509	0.031*
C3	0.4424 (2)	0.79280 (6)	0.32062 (18)	0.0232 (4)
H3A	0.419816	0.827862	0.315943	0.028*
H3B	0.432982	0.780416	0.229056	0.028*
C4	0.6335 (2)	0.78392 (6)	0.38858 (17)	0.0190 (3)
C5	0.6655 (2)	0.72984 (6)	0.40730 (16)	0.0175 (3)
C6	0.5124 (2)	0.69908 (5)	0.42489 (15)	0.0170 (3)
C7	0.5444 (2)	0.64570 (5)	0.45008 (16)	0.0164 (3)
H7A	0.668292	0.641386	0.497582	0.020*
C8	0.4092 (2)	0.62727 (5)	0.53860 (16)	0.0170 (3)
C9	0.2458 (2)	0.64791 (6)	0.53611 (16)	0.0185 (3)
C10	0.6615 (3)	0.80687 (7)	0.52669 (19)	0.0293 (4)
H10A	0.783401	0.799820	0.568766	0.044*
H10B	0.573604	0.793666	0.580624	0.044*
H10C	0.645383	0.841759	0.518702	0.044*
C11	0.7685 (2)	0.80522 (6)	0.30387 (19)	0.0261 (4)
H11A	0.756447	0.789038	0.217908	0.039*
H11B	0.890814	0.800633	0.348417	0.039*
H11C	0.744789	0.839655	0.290953	0.039*
C12	0.0930 (2)	0.63118 (6)	0.60675 (18)	0.0223 (3)
H12A	0.092211	0.595962	0.609755	0.033*
H12B	−0.020875	0.642682	0.559688	0.033*
H12C	0.107879	0.643951	0.696950	0.033*
C13	0.4600 (2)	0.58570 (6)	0.62451 (17)	0.0197 (3)
C14	0.6800 (2)	0.52376 (6)	0.67080 (18)	0.0233 (4)
H14A	0.579391	0.502405	0.690737	0.028*
C15	0.8005 (3)	0.49721 (7)	0.5873 (2)	0.0320 (4)
H15A	0.732182	0.488837	0.502190	0.048*
H15B	0.845165	0.467797	0.632940	0.048*
H15C	0.902333	0.517761	0.572403	0.048*
C16	0.7809 (3)	0.54265 (7)	0.79772 (19)	0.0321 (4)
H16A	0.698202	0.560747	0.846536	0.048*
H16B	0.878266	0.563824	0.777245	0.048*
H16C	0.831503	0.515642	0.851701	0.048*
C17	0.5305 (2)	0.61730 (5)	0.32111 (16)	0.0180 (3)
C18	0.6711 (2)	0.59070 (6)	0.28216 (17)	0.0221 (3)
C19	0.6575 (3)	0.56336 (6)	0.16787 (19)	0.0297 (4)
H19A	0.757188	0.545153	0.146365	0.036*
C20	0.4966 (3)	0.56302 (7)	0.08575 (18)	0.0310 (4)
H20A	0.484741	0.545016	0.006024	0.037*
C21	0.3531 (3)	0.58922 (7)	0.12102 (17)	0.0261 (4)
C22	0.3689 (2)	0.61593 (6)	0.23693 (17)	0.0216 (3)
H22A	0.268204	0.633535	0.259244	0.026*
C23	0.1789 (3)	0.58922 (8)	0.03321 (19)	0.0355 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0201 (5)	0.0332 (6)	0.0326 (6)	0.0071 (4)	0.0043 (4)	−0.0038 (5)
F2	0.0219 (8)	0.0783 (19)	0.0270 (8)	−0.0104 (9)	0.0018 (6)	−0.0014 (9)
F3	0.0451 (19)	0.0281 (10)	0.0418 (19)	−0.0055 (10)	−0.0127 (16)	0.0106 (11)
F4	0.0431 (12)	0.0323 (8)	0.0324 (9)	−0.0078 (7)	−0.0088 (8)	−0.0090 (7)
F2A	0.025 (3)	0.098 (6)	0.041 (3)	0.019 (3)	−0.011 (2)	−0.028 (4)
F3A	0.037 (5)	0.073 (8)	0.037 (6)	0.002 (6)	0.012 (5)	0.026 (5)
F4A	0.051 (4)	0.042 (3)	0.073 (6)	−0.023 (3)	−0.033 (4)	0.020 (4)
O1	0.0149 (6)	0.0213 (6)	0.0324 (7)	0.0021 (5)	0.0044 (5)	0.0027 (5)
O2	0.0299 (7)	0.0294 (6)	0.0297 (7)	0.0054 (5)	0.0138 (6)	0.0089 (5)
O3	0.0180 (6)	0.0186 (5)	0.0236 (6)	0.0031 (4)	0.0045 (5)	0.0039 (5)
N1	0.0119 (7)	0.0219 (7)	0.0285 (8)	0.0021 (5)	0.0039 (6)	0.0045 (6)
C1	0.0152 (8)	0.0202 (8)	0.0216 (8)	0.0017 (6)	0.0031 (6)	0.0013 (6)
C2	0.0171 (8)	0.0226 (8)	0.0372 (10)	0.0054 (6)	0.0055 (7)	0.0084 (7)
C3	0.0187 (9)	0.0198 (8)	0.0312 (9)	0.0051 (6)	0.0041 (7)	0.0068 (7)
C4	0.0168 (8)	0.0164 (7)	0.0238 (8)	0.0016 (6)	0.0029 (6)	0.0021 (6)
C5	0.0167 (8)	0.0187 (7)	0.0172 (7)	0.0013 (6)	0.0023 (6)	0.0000 (6)
C6	0.0161 (8)	0.0176 (7)	0.0171 (7)	0.0005 (6)	0.0016 (6)	0.0013 (6)
C7	0.0135 (7)	0.0177 (7)	0.0179 (7)	0.0012 (6)	0.0014 (6)	−0.0006 (6)
C8	0.0166 (8)	0.0172 (7)	0.0172 (7)	−0.0010 (6)	0.0019 (6)	−0.0013 (6)
C9	0.0182 (8)	0.0191 (7)	0.0181 (7)	−0.0018 (6)	0.0015 (6)	−0.0015 (6)
C10	0.0331 (11)	0.0224 (8)	0.0322 (10)	0.0024 (7)	0.0035 (8)	−0.0053 (7)
C11	0.0208 (9)	0.0215 (8)	0.0369 (10)	−0.0006 (7)	0.0071 (8)	0.0058 (7)
C12	0.0167 (8)	0.0245 (8)	0.0266 (9)	−0.0009 (6)	0.0068 (7)	0.0013 (7)
C13	0.0177 (8)	0.0198 (7)	0.0217 (8)	0.0008 (6)	0.0029 (6)	−0.0015 (6)
C14	0.0201 (9)	0.0186 (8)	0.0314 (9)	0.0017 (6)	0.0036 (7)	0.0077 (7)
C15	0.0261 (10)	0.0225 (9)	0.0485 (12)	0.0055 (7)	0.0082 (9)	0.0031 (8)
C16	0.0314 (11)	0.0334 (10)	0.0298 (10)	−0.0021 (8)	−0.0026 (8)	0.0104 (8)
C17	0.0205 (8)	0.0161 (7)	0.0178 (7)	−0.0029 (6)	0.0044 (6)	0.0013 (6)
C18	0.0220 (9)	0.0213 (8)	0.0237 (8)	−0.0006 (6)	0.0055 (7)	0.0002 (6)
C19	0.0375 (11)	0.0234 (9)	0.0311 (10)	−0.0030 (8)	0.0157 (9)	−0.0056 (7)
C20	0.0448 (12)	0.0281 (9)	0.0220 (9)	−0.0142 (8)	0.0109 (8)	−0.0067 (7)
C21	0.0305 (10)	0.0294 (9)	0.0181 (8)	−0.0139 (7)	0.0012 (7)	0.0030 (7)
C22	0.0221 (9)	0.0240 (8)	0.0190 (8)	−0.0048 (7)	0.0034 (7)	0.0032 (6)
C23	0.0409 (12)	0.0448 (11)	0.0196 (9)	−0.0198 (9)	−0.0006 (8)	0.0048 (8)

Geometric parameters (Å, º)

F1—C18	1.350 (2)	C8—C13	1.472 (2)
F2—C23	1.291 (3)	C9—C12	1.500 (2)
F3—C23	1.303 (4)	C10—H10A	0.9800
F4—C23	1.390 (3)	C10—H10B	0.9800
F2A—C23	1.632 (6)	C10—H10C	0.9800
F3A—C23	1.348 (13)	C11—H11A	0.9800
F4A—C23	1.223 (6)	C11—H11B	0.9800
O1—C5	1.233 (2)	C11—H11C	0.9800
O2—C13	1.215 (2)	C12—H12A	0.9800
O3—C13	1.3470 (19)	C12—H12B	0.9800
O3—C14	1.4607 (19)	C12—H12C	0.9800
N1—C1	1.370 (2)	C14—C15	1.508 (3)
N1—C9	1.394 (2)	C14—C16	1.511 (3)
N1—H1N	0.88 (2)	C14—H14A	1.0000
C1—C6	1.355 (2)	C15—H15A	0.9800
C1—C2	1.498 (2)	C15—H15B	0.9800
C2—C3	1.523 (2)	C15—H15C	0.9800
C2—H2A	0.9900	C16—H16A	0.9800
C2—H2B	0.9900	C16—H16B	0.9800
C3—C4	1.532 (2)	C16—H16C	0.9800
C3—H3A	0.9900	C17—C18	1.385 (2)
C3—H3B	0.9900	C17—C22	1.396 (2)
C4—C11	1.528 (2)	C18—C19	1.385 (2)
C4—C5	1.531 (2)	C19—C20	1.381 (3)
C4—C10	1.538 (2)	C19—H19A	0.9500
C5—C6	1.459 (2)	C20—C21	1.383 (3)
C6—C7	1.521 (2)	C20—H20A	0.9500
C7—C8	1.526 (2)	C21—C22	1.389 (2)
C7—C17	1.527 (2)	C21—C23	1.489 (3)
C7—H7A	1.0000	C22—H22A	0.9500
C8—C9	1.350 (2)
C13—O3—C14	116.69 (13)	C9—C12—H12B	109.5
C1—N1—C9	121.29 (14)	H12A—C12—H12B	109.5
C1—N1—H1N	120.3 (14)	C9—C12—H12C	109.5
C9—N1—H1N	117.5 (14)	H12A—C12—H12C	109.5
C6—C1—N1	120.53 (15)	H12B—C12—H12C	109.5
C6—C1—C2	123.60 (15)	O2—C13—O3	123.17 (15)
N1—C1—C2	115.80 (14)	O2—C13—C8	126.25 (15)
C1—C2—C3	111.35 (14)	O3—C13—C8	110.58 (13)
C1—C2—H2A	109.4	O3—C14—C15	105.20 (14)
C3—C2—H2A	109.4	O3—C14—C16	108.92 (14)
C1—C2—H2B	109.4	C15—C14—C16	112.55 (16)
C3—C2—H2B	109.4	O3—C14—H14A	110.0
H2A—C2—H2B	108.0	C15—C14—H14A	110.0
C2—C3—C4	113.03 (14)	C16—C14—H14A	110.0
C2—C3—H3A	109.0	C14—C15—H15A	109.5
C4—C3—H3A	109.0	C14—C15—H15B	109.5
C2—C3—H3B	109.0	H15A—C15—H15B	109.5
C4—C3—H3B	109.0	C14—C15—H15C	109.5
H3A—C3—H3B	107.8	H15A—C15—H15C	109.5
C11—C4—C5	110.31 (13)	H15B—C15—H15C	109.5
C11—C4—C3	109.16 (14)	C14—C16—H16A	109.5
C5—C4—C3	109.75 (13)	C14—C16—H16B	109.5
C11—C4—C10	109.38 (15)	H16A—C16—H16B	109.5
C5—C4—C10	106.97 (14)	C14—C16—H16C	109.5
C3—C4—C10	111.26 (14)	H16A—C16—H16C	109.5
O1—C5—C6	120.70 (14)	H16B—C16—H16C	109.5
O1—C5—C4	120.64 (14)	C18—C17—C22	116.21 (15)
C6—C5—C4	118.56 (14)	C18—C17—C7	123.34 (15)
C1—C6—C5	121.08 (14)	C22—C17—C7	120.43 (15)
C1—C6—C7	119.93 (14)	F1—C18—C17	119.05 (15)
C5—C6—C7	118.91 (14)	F1—C18—C19	117.23 (16)
C6—C7—C8	109.00 (13)	C17—C18—C19	123.71 (18)
C6—C7—C17	111.51 (13)	C20—C19—C18	118.87 (18)
C8—C7—C17	110.85 (13)	C20—C19—H19A	120.6
C6—C7—H7A	108.5	C18—C19—H19A	120.6
C8—C7—H7A	108.5	C19—C20—C21	119.17 (17)
C17—C7—H7A	108.5	C19—C20—H20A	120.4
C9—C8—C13	120.85 (15)	C21—C20—H20A	120.4
C9—C8—C7	120.83 (14)	C20—C21—C22	121.04 (18)
C13—C8—C7	118.31 (14)	C20—C21—C23	119.70 (17)
C8—C9—N1	119.18 (14)	C22—C21—C23	119.26 (18)
C8—C9—C12	127.09 (15)	C21—C22—C17	120.99 (17)
N1—C9—C12	113.69 (14)	C21—C22—H22A	119.5
C4—C10—H10A	109.5	C17—C22—H22A	119.5
C4—C10—H10B	109.5	F2—C23—F3	111.3 (3)
H10A—C10—H10B	109.5	F4A—C23—F3A	111.0 (8)
C4—C10—H10C	109.5	F2—C23—F4	105.48 (18)
H10A—C10—H10C	109.5	F3—C23—F4	105.1 (2)
H10B—C10—H10C	109.5	F4A—C23—C21	125.0 (3)
C4—C11—H11A	109.5	F2—C23—C21	111.93 (16)
C4—C11—H11B	109.5	F3—C23—C21	113.0 (3)
H11A—C11—H11B	109.5	F3A—C23—C21	117.5 (9)
C4—C11—H11C	109.5	F4—C23—C21	109.55 (19)
H11A—C11—H11C	109.5	F4A—C23—F2A	93.9 (5)
H11B—C11—H11C	109.5	F3A—C23—F2A	88.7 (8)
C9—C12—H12A	109.5	C21—C23—F2A	111.1 (2)
C9—N1—C1—C6	16.7 (2)	C14—O3—C13—C8	177.28 (13)
C9—N1—C1—C2	−160.28 (16)	C9—C8—C13—O2	−14.5 (3)
C6—C1—C2—C3	16.0 (3)	C7—C8—C13—O2	166.88 (17)
N1—C1—C2—C3	−167.16 (16)	C9—C8—C13—O3	166.01 (15)
C1—C2—C3—C4	−47.4 (2)	C7—C8—C13—O3	−12.6 (2)
C2—C3—C4—C11	174.92 (14)	C13—O3—C14—C15	161.43 (15)
C2—C3—C4—C5	53.91 (19)	C13—O3—C14—C16	−77.70 (18)
C2—C3—C4—C10	−64.28 (19)	C6—C7—C17—C18	119.37 (17)
C11—C4—C5—O1	33.3 (2)	C8—C7—C17—C18	−118.98 (17)
C3—C4—C5—O1	153.65 (15)	C6—C7—C17—C22	−62.54 (19)
C10—C4—C5—O1	−85.53 (19)	C8—C7—C17—C22	59.10 (19)
C11—C4—C5—C6	−150.30 (15)	C22—C17—C18—F1	179.63 (14)
C3—C4—C5—C6	−30.0 (2)	C7—C17—C18—F1	−2.2 (2)
C10—C4—C5—C6	90.83 (18)	C22—C17—C18—C19	−0.7 (2)
N1—C1—C6—C5	−168.50 (15)	C7—C17—C18—C19	177.43 (16)
C2—C1—C6—C5	8.2 (3)	F1—C18—C19—C20	−178.98 (15)
N1—C1—C6—C7	8.1 (2)	C17—C18—C19—C20	1.4 (3)
C2—C1—C6—C7	−175.12 (16)	C18—C19—C20—C21	−1.2 (3)
O1—C5—C6—C1	175.91 (16)	C19—C20—C21—C22	0.4 (3)
C4—C5—C6—C1	−0.4 (2)	C19—C20—C21—C23	179.90 (17)
O1—C5—C6—C7	−0.8 (2)	C20—C21—C22—C17	0.3 (3)
C4—C5—C6—C7	−177.12 (14)	C23—C21—C22—C17	−179.26 (15)
C1—C6—C7—C8	−28.8 (2)	C18—C17—C22—C21	−0.1 (2)
C5—C6—C7—C8	147.86 (14)	C7—C17—C22—C21	−178.31 (15)
C1—C6—C7—C17	93.87 (18)	C20—C21—C23—F4A	71.2 (7)
C5—C6—C7—C17	−89.42 (17)	C22—C21—C23—F4A	−109.2 (7)
C6—C7—C8—C9	29.1 (2)	C20—C21—C23—F2	137.6 (2)
C17—C7—C8—C9	−93.96 (18)	C22—C21—C23—F2	−42.9 (3)
C6—C7—C8—C13	−152.26 (14)	C20—C21—C23—F3	−95.8 (3)
C17—C7—C8—C13	84.64 (18)	C22—C21—C23—F3	83.7 (3)
C13—C8—C9—N1	172.97 (15)	C20—C21—C23—F3A	−77.8 (8)
C7—C8—C9—N1	−8.5 (2)	C22—C21—C23—F3A	101.8 (8)
C13—C8—C9—C12	−4.9 (3)	C20—C21—C23—F4	21.0 (2)
C7—C8—C9—C12	173.69 (15)	C22—C21—C23—F4	−159.50 (17)
C1—N1—C9—C8	−16.5 (2)	C20—C21—C23—F2A	−177.7 (4)
C1—N1—C9—C12	161.63 (15)	C22—C21—C23—F2A	1.8 (4)
C14—O3—C13—O2	−2.2 (2)

Hydrogen-bond geometry (Å, º)

Cg3 is the centroid of the C17–C22 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.88 (2)	2.12 (2)	2.9798 (19)	165 (2)
C2—H2A···F3^ii	0.99	2.59	3.187 (4)	119
C12—H12B···F1^i	0.98	2.64	3.206 (2)	117
C12—H12B···O1^i	0.98	2.65	3.505 (2)	145
C12—H12C···F3A^iii	0.98	2.43	3.243 (15)	141
C16—H16A···O2	0.98	2.59	3.106 (2)	113
C16—H16C···F4A^iv	0.98	2.43	3.409 (6)	174
C19—H19A···F2^v	0.95	2.52	3.117 (3)	121
C10—H10C···Cg3^ii	0.98	2.93	3.631 (2)	130
C14—H14A···Cg3^iv	1.00	2.91	3.7707 (18)	145

Symmetry codes: (i) x−1, y, z; (ii) x, −y+3/2, z+1/2; (iii) x, y, z+1; (iv) −x+1, −y+1, −z+1; (v) x+1, y, z.