Crystal structure of (1S,2S,2′R,3a′S,5R)-2′-[(5-bromo-1H-indol-3-yl)meth­yl]-2-isopropyl-5,5′-dimethyl­dihydro-2′H-spiro­[cyclo­hexane-1,6′-imidazo[1,5-b]isoxazol]-4′(5′H)-one

The absolute structure for the title compound, which has five chiral centres has been determined in this analysis. The supra­molecular architecture comprises parallel zigzag chains formed through N—H...N and C—H...O hydrogen bonds, as well as intra­molecular C—H...O, C—H...N and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.053
• wR factor = 0.135
• Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C20 Check
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............       0.01 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported Hn1    ..  O1      ..       2.66 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          3 Report
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         86 %

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2 Note
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT180_ALERT_4_G Check Cell Rounding: # of Values Ending with 0 =          3 Note
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C24 Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          1 Note
PLAT791_ALERT_4_G The Model has Chirality at C10     (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C12     (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C14     (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C16     (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C19     (Chiral SPGR)          S Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          2 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           1 Note

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
  10 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SIR2011 (Burla et al., 2012); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

(1S,2S,2'R,3a'S,5R)-2'-[(5-Bromo-1H-indol-3-yl)methyl]-2-isopropyl-5,5'-dimethyldihydro-2'H-spiro[cyclohexane-1,6'-imidazo[1,5-b]isoxazol]-4'(5'H)-one

Crystal data

C24H32BrN3O2	F(000) = 496
Mr = 474.43	Dx = 1.328 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 10.2640 (5) Å	Cell parameters from 8154 reflections
b = 9.6480 (5) Å	θ = 1.0–27.9°
c = 12.0480 (5) Å	µ = 1.76 mm^−1
β = 96.204 (5)°	T = 293 K
V = 1186.09 (10) Å^3	Plate, colorless
Z = 2	0.46 × 0.39 × 0.11 mm

Data collection

Oxford Diffraction Xcalibur Atlas Gemini Ultra CCD diffractometer	4337 independent reflections
Radiation source: Enhance (Mo) X-ray source)	2924 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.104
ω/2θ scans	θmax = 26.0°, θmin = 2.7°
Absorption correction: multi-scan (SCALEPACK; Otwinowski et al., 1997)	h = −12→12
Tmin = 0.455, Tmax = 0.802	k = −11→11
10653 measured reflections	l = −13→14

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.053	w = 1/[σ^2(Fo^2) + (0.0631P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.135	(Δ/σ)max < 0.001
S = 0.97	Δρmax = 0.31 e Å^−3
4337 reflections	Δρmin = −0.51 e Å^−3
272 parameters	Absolute structure: Flack x determined using 1005 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
2 restraints	Absolute structure parameter: −0.013 (13)

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
Br	0.17985 (7)	0.23216 (8)	0.27079 (6)	0.0716 (3)
O1	0.4307 (4)	0.4046 (5)	0.6482 (4)	0.0455 (11)
N3	0.3297 (6)	0.6276 (6)	0.8208 (5)	0.0559 (16)
O2	0.5063 (6)	0.6393 (6)	0.9554 (4)	0.0728 (16)
N2	0.3578 (5)	0.4065 (6)	0.7471 (4)	0.0419 (12)
N1	0.6516 (6)	0.6022 (6)	0.3324 (5)	0.0521 (15)
C14	0.2644 (7)	0.5267 (7)	0.7427 (5)	0.0447 (15)
C6	0.4147 (7)	0.3475 (8)	0.3841 (6)	0.0472 (16)
H6	0.4007	0.2871	0.4418	0.057*
C9	0.6468 (6)	0.4016 (8)	0.5952 (5)	0.0478 (16)
H9A	0.7375	0.4153	0.6248	0.057*
H9B	0.6317	0.3025	0.5885	0.057*
C1	0.3301 (7)	0.3486 (8)	0.2869 (6)	0.0523 (18)
C11	0.5918 (7)	0.4126 (9)	0.7977 (6)	0.0513 (18)
H11A	0.6196	0.3164	0.8013	0.062*
H11B	0.6594	0.4698	0.8372	0.062*
C10	0.5591 (6)	0.4605 (7)	0.6774 (5)	0.0426 (15)
H10	0.5572	0.5619	0.6734	0.051*
C8	0.6248 (6)	0.4659 (7)	0.4806 (5)	0.0439 (15)
C13	0.4388 (7)	0.5769 (8)	0.8831 (6)	0.0523 (18)
C19	0.1319 (7)	0.4750 (8)	0.7834 (5)	0.0485 (17)
H19	0.0774	0.5582	0.7854	0.058*
C5	0.5213 (6)	0.4378 (7)	0.3948 (5)	0.0428 (15)
C12	0.4609 (6)	0.4315 (8)	0.8439 (5)	0.0471 (16)
H12	0.4518	0.3648	0.9039	0.057*
C16	0.1585 (6)	0.4977 (7)	0.5389 (5)	0.0472 (16)
H16	0.2112	0.4153	0.5275	0.057*
C15	0.2358 (7)	0.5914 (7)	0.6262 (6)	0.0500 (17)
H15A	0.3184	0.6159	0.5992	0.060*
H15B	0.1867	0.6764	0.6328	0.060*
C7	0.6991 (6)	0.5668 (8)	0.4386 (6)	0.0503 (17)
H7	0.7730	0.6064	0.4776	0.060*
C4	0.5407 (7)	0.5268 (7)	0.3039 (6)	0.0459 (16)
C18	0.0585 (7)	0.3816 (8)	0.6964 (6)	0.0544 (18)
H18A	−0.0241	0.3541	0.7220	0.065*
H18B	0.1096	0.2983	0.6884	0.065*
C3	0.4561 (8)	0.5248 (8)	0.2046 (6)	0.056 (2)
H3	0.4705	0.5828	0.1455	0.068*
C17	0.0316 (6)	0.4521 (9)	0.5829 (6)	0.0574 (19)
H17A	−0.0146	0.3883	0.5302	0.069*
H17B	−0.0241	0.5322	0.5896	0.069*
C21	0.1702 (8)	0.2603 (9)	0.9120 (6)	0.071 (2)
H21A	0.2474	0.2388	0.8770	0.107*
H21B	0.1833	0.2340	0.9892	0.107*
H21C	0.0968	0.2105	0.8754	0.107*
C2	0.3522 (8)	0.4357 (8)	0.1965 (6)	0.061 (2)
H2	0.2954	0.4324	0.1309	0.073*
C20	0.1432 (7)	0.4168 (9)	0.9030 (6)	0.0554 (18)
H20	0.2168	0.4641	0.9457	0.066*
C23	0.1317 (8)	0.5741 (9)	0.4278 (6)	0.068 (2)
H23A	0.2133	0.6015	0.4022	0.102*
H23B	0.0854	0.5139	0.3736	0.102*
H23C	0.0796	0.6549	0.4376	0.102*
C22	0.0205 (10)	0.4502 (13)	0.9589 (8)	0.097 (3)
H22A	0.0032	0.5479	0.9535	0.145*
H22B	−0.0527	0.4001	0.9222	0.145*
H22C	0.0338	0.4236	1.0361	0.145*
C24	0.2777 (9)	0.7638 (8)	0.8427 (8)	0.081 (3)
H24A	0.2015	0.7815	0.7912	0.121*
H24B	0.2542	0.7668	0.9177	0.121*
H24C	0.3431	0.8329	0.8338	0.121*
HN1	0.6758	0.6699	0.2885	0.07 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br	0.0695 (5)	0.0753 (5)	0.0667 (5)	−0.0179 (5)	−0.0081 (3)	0.0009 (5)
O1	0.042 (3)	0.058 (3)	0.036 (3)	−0.003 (2)	0.0033 (19)	0.000 (2)
N3	0.066 (4)	0.049 (4)	0.052 (4)	−0.006 (3)	0.004 (3)	−0.008 (3)
O2	0.078 (4)	0.092 (4)	0.047 (3)	−0.029 (3)	−0.001 (3)	−0.015 (3)
N2	0.042 (3)	0.053 (3)	0.031 (3)	−0.002 (3)	0.002 (2)	0.001 (2)
N1	0.059 (4)	0.049 (4)	0.049 (4)	−0.007 (3)	0.012 (3)	0.004 (3)
C14	0.051 (4)	0.046 (4)	0.037 (4)	0.000 (3)	0.002 (3)	−0.003 (3)
C6	0.058 (4)	0.048 (4)	0.037 (4)	−0.004 (3)	0.009 (3)	0.005 (3)
C9	0.043 (4)	0.056 (4)	0.045 (4)	0.012 (3)	0.006 (3)	0.011 (3)
C1	0.067 (5)	0.047 (4)	0.042 (4)	−0.001 (4)	−0.001 (3)	−0.007 (3)
C11	0.045 (4)	0.070 (5)	0.037 (4)	0.003 (4)	−0.002 (3)	0.007 (4)
C10	0.040 (3)	0.049 (4)	0.038 (4)	−0.006 (3)	0.003 (3)	0.000 (3)
C8	0.042 (3)	0.049 (4)	0.041 (4)	0.000 (3)	0.009 (3)	−0.001 (3)
C13	0.058 (4)	0.062 (5)	0.038 (4)	−0.013 (4)	0.008 (3)	−0.001 (3)
C19	0.048 (4)	0.052 (4)	0.046 (4)	0.009 (3)	0.006 (3)	0.002 (3)
C5	0.048 (4)	0.043 (4)	0.038 (4)	0.004 (3)	0.008 (3)	−0.003 (3)
C12	0.046 (4)	0.060 (5)	0.034 (3)	−0.009 (3)	0.003 (3)	0.003 (3)
C16	0.051 (4)	0.044 (4)	0.045 (4)	0.006 (3)	−0.003 (3)	0.004 (3)
C15	0.058 (4)	0.037 (4)	0.054 (5)	0.008 (3)	0.003 (3)	0.008 (3)
C7	0.047 (4)	0.054 (4)	0.051 (4)	−0.005 (4)	0.009 (3)	−0.004 (3)
C4	0.057 (4)	0.038 (4)	0.043 (4)	0.001 (3)	0.011 (3)	−0.003 (3)
C18	0.044 (4)	0.067 (5)	0.050 (4)	−0.002 (3)	0.000 (3)	−0.003 (4)
C3	0.075 (5)	0.055 (5)	0.039 (4)	0.003 (4)	0.009 (4)	0.003 (3)
C17	0.048 (4)	0.069 (5)	0.052 (4)	0.003 (4)	−0.007 (3)	−0.001 (4)
C21	0.073 (5)	0.085 (7)	0.057 (5)	−0.006 (5)	0.015 (4)	0.015 (4)
C2	0.082 (5)	0.061 (5)	0.036 (4)	−0.007 (4)	−0.008 (3)	0.000 (4)
C20	0.051 (4)	0.072 (5)	0.045 (4)	0.002 (4)	0.012 (3)	−0.002 (4)
C23	0.090 (6)	0.065 (5)	0.045 (4)	0.011 (5)	−0.011 (4)	0.006 (4)
C22	0.087 (6)	0.139 (9)	0.071 (6)	0.021 (7)	0.037 (5)	0.009 (6)
C24	0.104 (6)	0.063 (7)	0.075 (6)	0.002 (5)	0.009 (5)	−0.021 (5)

Geometric parameters (Å, º)

Br—C1	1.901 (7)	C5—C4	1.423 (9)
O1—C10	1.432 (7)	C12—H12	0.9800
O1—N2	1.475 (6)	C16—C17	1.523 (10)
N3—C13	1.369 (10)	C16—C23	1.526 (10)
N3—C24	1.453 (10)	C16—C15	1.540 (10)
N3—C14	1.465 (9)	C16—H16	0.9800
O2—C13	1.212 (9)	C15—H15A	0.9700
N2—C14	1.502 (9)	C15—H15B	0.9700
N2—C12	1.507 (8)	C7—H7	0.9300
N1—C7	1.362 (9)	C4—C3	1.401 (11)
N1—C4	1.362 (9)	C18—C17	1.526 (10)
N1—HN1	0.8929	C18—H18A	0.9700
C14—C15	1.535 (9)	C18—H18B	0.9700
C14—C19	1.576 (10)	C3—C2	1.365 (11)
C6—C1	1.381 (10)	C3—H3	0.9300
C6—C5	1.394 (10)	C17—H17A	0.9700
C6—H6	0.9300	C17—H17B	0.9700
C9—C8	1.508 (9)	C21—C20	1.537 (12)
C9—C10	1.519 (9)	C21—H21A	0.9600
C9—H9A	0.9700	C21—H21B	0.9600
C9—H9B	0.9700	C21—H21C	0.9600
C1—C2	1.413 (11)	C2—H2	0.9300
C11—C12	1.519 (9)	C20—C22	1.525 (10)
C11—C10	1.524 (9)	C20—H20	0.9800
C11—H11A	0.9700	C23—H23A	0.9600
C11—H11B	0.9700	C23—H23B	0.9600
C10—H10	0.9800	C23—H23C	0.9600
C8—C7	1.368 (9)	C22—H22A	0.9600
C8—C5	1.426 (9)	C22—H22B	0.9600
C13—C12	1.506 (11)	C22—H22C	0.9600
C19—C18	1.519 (10)	C24—H24A	0.9600
C19—C20	1.540 (10)	C24—H24B	0.9600
C19—H19	0.9800	C24—H24C	0.9600
C10—O1—N2	109.3 (4)	C17—C16—H16	108.6
C13—N3—C24	121.2 (7)	C23—C16—H16	108.6
C13—N3—C14	113.9 (6)	C15—C16—H16	108.6
C24—N3—C14	124.5 (7)	C14—C15—C16	114.8 (5)
O1—N2—C14	111.0 (5)	C14—C15—H15A	108.6
O1—N2—C12	104.6 (4)	C16—C15—H15A	108.6
C14—N2—C12	107.2 (5)	C14—C15—H15B	108.6
C7—N1—C4	107.9 (6)	C16—C15—H15B	108.6
C7—N1—HN1	130.2	H15A—C15—H15B	107.5
C4—N1—HN1	121.3	N1—C7—C8	111.6 (6)
N3—C14—N2	104.1 (5)	N1—C7—H7	124.2
N3—C14—C15	110.2 (5)	C8—C7—H7	124.2
N2—C14—C15	113.9 (5)	N1—C4—C3	130.3 (7)
N3—C14—C19	111.1 (5)	N1—C4—C5	108.1 (6)
N2—C14—C19	108.3 (5)	C3—C4—C5	121.6 (7)
C15—C14—C19	109.1 (5)	C19—C18—C17	112.5 (6)
C1—C6—C5	119.2 (6)	C19—C18—H18A	109.1
C1—C6—H6	120.4	C17—C18—H18A	109.1
C5—C6—H6	120.4	C19—C18—H18B	109.1
C8—C9—C10	113.7 (5)	C17—C18—H18B	109.1
C8—C9—H9A	108.8	H18A—C18—H18B	107.8
C10—C9—H9A	108.8	C2—C3—C4	118.5 (7)
C8—C9—H9B	108.8	C2—C3—H3	120.7
C10—C9—H9B	108.8	C4—C3—H3	120.7
H9A—C9—H9B	107.7	C16—C17—C18	111.2 (5)
C6—C1—C2	121.4 (7)	C16—C17—H17A	109.4
C6—C1—Br	120.7 (6)	C18—C17—H17A	109.4
C2—C1—Br	117.9 (6)	C16—C17—H17B	109.4
C12—C11—C10	101.5 (5)	C18—C17—H17B	109.4
C12—C11—H11A	111.5	H17A—C17—H17B	108.0
C10—C11—H11A	111.5	C20—C21—H21A	109.5
C12—C11—H11B	111.5	C20—C21—H21B	109.5
C10—C11—H11B	111.5	H21A—C21—H21B	109.5
H11A—C11—H11B	109.3	C20—C21—H21C	109.5
O1—C10—C9	107.0 (5)	H21A—C21—H21C	109.5
O1—C10—C11	102.8 (5)	H21B—C21—H21C	109.5
C9—C10—C11	114.9 (5)	C3—C2—C1	120.5 (7)
O1—C10—H10	110.6	C3—C2—H2	119.7
C9—C10—H10	110.6	C1—C2—H2	119.7
C11—C10—H10	110.6	C22—C20—C21	109.1 (8)
C7—C8—C5	105.6 (6)	C22—C20—C19	110.7 (7)
C7—C8—C9	126.7 (6)	C21—C20—C19	114.7 (6)
C5—C8—C9	127.7 (6)	C22—C20—H20	107.3
O2—C13—N3	125.9 (8)	C21—C20—H20	107.3
O2—C13—C12	126.4 (7)	C19—C20—H20	107.3
N3—C13—C12	107.6 (6)	C16—C23—H23A	109.5
C18—C19—C20	114.3 (6)	C16—C23—H23B	109.5
C18—C19—C14	110.7 (6)	H23A—C23—H23B	109.5
C20—C19—C14	115.3 (6)	C16—C23—H23C	109.5
C18—C19—H19	105.2	H23A—C23—H23C	109.5
C20—C19—H19	105.2	H23B—C23—H23C	109.5
C14—C19—H19	105.2	C20—C22—H22A	109.5
C6—C5—C4	118.7 (6)	C20—C22—H22B	109.5
C6—C5—C8	134.6 (6)	H22A—C22—H22B	109.5
C4—C5—C8	106.7 (6)	C20—C22—H22C	109.5
C13—C12—N2	105.9 (6)	H22A—C22—H22C	109.5
C13—C12—C11	113.3 (6)	H22B—C22—H22C	109.5
N2—C12—C11	105.8 (5)	N3—C24—H24A	109.5
C13—C12—H12	110.5	N3—C24—H24B	109.5
N2—C12—H12	110.5	H24A—C24—H24B	109.5
C11—C12—H12	110.5	N3—C24—H24C	109.5
C17—C16—C23	111.4 (6)	H24A—C24—H24C	109.5
C17—C16—C15	109.2 (6)	H24B—C24—H24C	109.5
C23—C16—C15	110.3 (6)
C10—O1—N2—C12	−14.5 (6)	C8—C5—C6—C1	179.1 (7)
C10—O1—N2—C14	100.9 (5)	C4—C5—C8—C7	−0.1 (7)
N2—O1—C10—C9	155.8 (5)	C4—C5—C8—C9	178.3 (6)
N2—O1—C10—C11	34.4 (6)	C6—C5—C8—C7	179.7 (8)
C7—N1—C4—C3	−179.9 (8)	C6—C5—C8—C9	−1.9 (13)
C7—N1—C4—C5	−2.0 (8)	N1—C7—C8—C5	−1.2 (8)
C4—N1—C7—C8	2.0 (8)	N1—C7—C8—C9	−179.6 (6)
O1—N2—C12—C11	−11.6 (7)	C5—C8—C9—C10	−78.1 (9)
O1—N2—C12—C13	109.0 (5)	C7—C8—C9—C10	100.1 (8)
C14—N2—C12—C11	−129.6 (6)	C8—C9—C10—O1	74.7 (7)
C14—N2—C12—C13	−9.0 (6)	C8—C9—C10—C11	−171.8 (6)
O1—N2—C14—N3	−103.0 (5)	O1—C10—C11—C12	−39.7 (7)
O1—N2—C14—C15	17.2 (7)	C9—C10—C11—C12	−155.6 (6)
O1—N2—C14—C19	138.7 (5)	C10—C11—C12—N2	31.3 (7)
C12—N2—C14—N3	10.8 (6)	C10—C11—C12—C13	−84.4 (7)
C12—N2—C14—C15	130.9 (6)	N2—C12—C13—O2	−175.3 (7)
C12—N2—C14—C19	−107.6 (5)	N2—C12—C13—N3	3.5 (7)
C14—N3—C13—O2	−177.5 (7)	C11—C12—C13—O2	−59.8 (10)
C14—N3—C13—C12	3.6 (8)	C11—C12—C13—N3	119.1 (6)
C24—N3—C13—O2	−4.7 (12)	N2—C14—C15—C16	67.4 (8)
C24—N3—C13—C12	176.5 (6)	N3—C14—C15—C16	−176.0 (6)
C13—N3—C14—N2	−9.2 (7)	C19—C14—C15—C16	−53.7 (7)
C13—N3—C14—C15	−131.7 (6)	N2—C14—C19—C18	−71.8 (7)
C13—N3—C14—C19	107.2 (7)	N2—C14—C19—C20	59.8 (7)
C24—N3—C14—N2	178.3 (6)	N3—C14—C19—C18	174.4 (6)
C24—N3—C14—C15	55.8 (9)	N3—C14—C19—C20	−54.0 (8)
C24—N3—C14—C19	−65.3 (8)	C15—C14—C19—C18	52.6 (7)
Br—C1—C2—C3	177.9 (6)	C15—C14—C19—C20	−175.8 (6)
C6—C1—C2—C3	−2.2 (12)	C14—C15—C16—C17	55.4 (8)
Br—C1—C6—C5	−177.7 (5)	C14—C15—C16—C23	178.1 (6)
C2—C1—C6—C5	2.4 (11)	C15—C16—C17—C18	−55.5 (8)
C1—C2—C3—C4	0.6 (12)	C23—C16—C17—C18	−177.4 (6)
C2—C3—C4—N1	178.3 (7)	C16—C17—C18—C19	58.6 (8)
C2—C3—C4—C5	0.7 (11)	C17—C18—C19—C14	−56.6 (8)
N1—C4—C5—C6	−178.5 (6)	C17—C18—C19—C20	171.3 (6)
N1—C4—C5—C8	1.3 (8)	C14—C19—C20—C21	−89.9 (8)
C3—C4—C5—C6	−0.4 (10)	C14—C19—C20—C22	146.0 (7)
C3—C4—C5—C8	179.4 (7)	C18—C19—C20—C21	40.0 (9)
C4—C5—C6—C1	−1.1 (10)	C18—C19—C20—C22	−84.1 (9)

Hydrogen-bond geometry (Å, º)

Cg3 is the centroid of the N2/C12/C13/N3/C14 five-membered imidazolidinone ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···N2^i	0.89	2.34	3.087 (8)	141
C3—H3···O2^ii	0.93	2.42	3.292 (9)	156
C16—H16···O1	0.98	2.55	3.091 (8)	115
C20—H20···N3	0.98	2.54	3.032 (10)	111
C21—H21A···N2	0.96	2.60	3.236 (9)	124
N1—HN1···O1^i	0.89	2.66	3.053 (8)	108
C20—H20···Cg3	0.98	2.41	2.866 (8)	104

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