Tautomerism troubles: proton transfer modifies the stereochemical assignments in diastereoisomeric structures of spiro­cyclic 5-methyl-2H-imidazol-4-amine dimers

Single-crystal structure analysis was required to correctly identify the mol­ecular structure and stereochemistry assignment of unexpected impurities in the preparation of a novel pharmaceutical spiro­cyclic imidazole-amine compound.

Key indicators

Structure: 2

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.022
• wR factor = 0.056
• Data-to-parameter ratio = 13.4

Structure: 1

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.024
• wR factor = 0.057
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Datablock: 2


Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         17 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          2 Report
PLAT142_ALERT_4_G s.u. on b - Axis Small or Missing ..............    0.00005 Ang.
PLAT143_ALERT_4_G s.u. on c - Axis Small or Missing ..............    0.00014 Ang.
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          1 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          9 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        36% Note
PLAT793_ALERT_4_G Model has Chirality at C4          (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C22         (Centro SPGR)          R Verify
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         15 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          5 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         19 Info

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

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




Datablock: 1


Alert level C
PLAT220_ALERT_2_C NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range        3.8 Ratio
PLAT222_ALERT_3_C NonSolvent Resd 1  H   Uiso(max)/Uiso(min) Range        4.5 Ratio
PLAT411_ALERT_2_C Short Inter H...H Contact  H6       ..H14A     .       2.12 Ang.
                                         1/2-x,-1/2+y,3/2-z  =      2_546 Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2 Note
PLAT013_ALERT_1_G N.O.K.   _shelx_hkl_checksum Found in CIF ......     Please Check
PLAT142_ALERT_4_G s.u. on b - Axis Small or Missing ..............    0.00008 Ang.
PLAT143_ALERT_4_G s.u. on c - Axis Small or Missing ..............    0.00008 Ang.
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT793_ALERT_4_G Model has Chirality at C4          (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C22         (Centro SPGR)          R Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         19 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
  10 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   5 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

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Computing details

For both structures, data collection: CrysAlis PRO (Rigaku OD, 2019); cell refinement: CrysAlis PRO (Rigaku OD, 2019); data reduction: CrysAlis PRO (Rigaku OD, 2019); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

(R,R)/(S,S)-(1r,1'S,4S,E)-6'-Bromo-N-[(1r,1'S,4S)-6'-bromo-4-methoxy-4''-methyl-3'H-dispiro[cyclohexane-1,2'-indene-1',2''-imidazol-5''-yl]-4-methoxy-4''-methyl-3'H-dispiro[cyclohexane-1,2'-indene-1',2''-imidazol]-5''-imine (2)

Crystal data

C36H41Br2N5O2	F(000) = 1512
Mr = 735.56	Dx = 1.474 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
a = 10.18956 (5) Å	Cell parameters from 82488 reflections
b = 13.92084 (5) Å	θ = 3.2–70.3°
c = 25.48643 (14) Å	µ = 3.42 mm^−1
β = 113.5742 (7)°	T = 100 K
V = 3313.47 (3) Å^3	Block, colourless
Z = 4	0.18 × 0.05 × 0.03 mm

Data collection

Rigaku 007HF equipped with Varimax confocal mirrors and an AFC11 goniometer and HyPix 6000 detector diffractometer	6068 independent reflections
Radiation source: Rotating anode, Rigaku 007 HF	5967 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.031
Detector resolution: 10 pixels mm^-1	θmax = 68.2°, θmin = 3.7°
profile data from ω–scans	h = −12→12
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2019)	k = −16→16
Tmin = 0.621, Tmax = 1.000	l = −30→30
118177 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.022	w = 1/[σ^2(Fo^2) + (0.0259P)^2 + 2.2368P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.056	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.33 e Å^−3
6068 reflections	Δρmin = −0.39 e Å^−3
454 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
15 restraints	Extinction coefficient: 0.00013 (2)
Primary atom site location: dual

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.

Refinement. This diastereoisomer has crystallised in the centrosymmetric space group P2₁/n; meaning that both RS and SR forms of the API must be present in equal amounts within the crystal. The atoms of both methoxy groups (O1, C18 and O2, C36), have been modelled as single sites with large thermal ellipsoids. This was found to be the most appropriate model; however, these large ellipsoids result in two checkCIF C-alerts. The N2-H2 bond length has been restrained, otherwise it refined to an unrealistic value.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1A	0.94977 (8)	−0.13936 (5)	0.43736 (3)	0.0374 (2)	0.892 (3)
Br1B	0.9408 (7)	−0.1378 (3)	0.4382 (2)	0.0172 (9)*	0.108 (3)
Br2	1.07263 (2)	−0.11819 (2)	0.78926 (2)	0.02647 (6)
C1	0.53448 (14)	0.13684 (9)	0.50383 (6)	0.0145 (3)
C2	0.43133 (15)	0.12704 (10)	0.44275 (6)	0.0165 (3)
C3	0.27976 (15)	0.09625 (11)	0.42505 (6)	0.0202 (3)
H3A	0.229686	0.101766	0.383384	0.030*
H3B	0.232780	0.137362	0.443573	0.030*
H3C	0.277007	0.029346	0.436529	0.030*
C4	0.63956 (15)	0.17633 (11)	0.44190 (6)	0.0193 (3)
C5A	0.7365 (5)	0.1160 (3)	0.4219 (2)	0.0222 (4)	0.892 (3)
C5B	0.726 (5)	0.1225 (19)	0.4235 (19)	0.0203 (18)*	0.108 (3)
C6B	0.779 (5)	0.0303 (19)	0.4395 (18)	0.0203 (18)*	0.108 (3)
H6B	0.758545	−0.003496	0.467690	0.024*	0.108 (3)
C7B	0.862 (4)	−0.0124 (15)	0.4141 (16)	0.0203 (18)*	0.108 (3)
C8B	0.892 (3)	0.0371 (14)	0.3728 (13)	0.0203 (18)*	0.108 (3)
H8B	0.949075	0.007835	0.355409	0.024*	0.108 (3)
C9B	0.839 (4)	0.1293 (14)	0.3568 (14)	0.0203 (18)*	0.108 (3)
H9B	0.859224	0.163089	0.328615	0.024*	0.108 (3)
C10B	0.756 (5)	0.1720 (15)	0.3822 (17)	0.0203 (18)*	0.108 (3)
C6A	0.7881 (6)	0.0251 (3)	0.4394 (2)	0.0232 (4)	0.892 (3)
H6A	0.764777	−0.009365	0.466683	0.028*	0.892 (3)
C7A	0.8764 (5)	−0.0138 (2)	0.41507 (19)	0.0295 (6)	0.892 (3)
C8A	0.9095 (4)	0.0346 (3)	0.37454 (17)	0.0378 (7)	0.892 (3)
H8A	0.969356	0.005467	0.358518	0.045*	0.892 (3)
C9A	0.8551 (5)	0.1254 (3)	0.35756 (19)	0.0400 (8)	0.892 (3)
H9A	0.877176	0.159069	0.329666	0.048*	0.892 (3)
C10A	0.7676 (6)	0.1679 (2)	0.3814 (2)	0.0308 (6)	0.892 (3)
C11A	0.6999 (8)	0.2652 (3)	0.3726 (2)	0.0333 (7)	0.892 (3)
H11A	0.608818	0.266382	0.338153	0.040*	0.892 (3)
H11B	0.764944	0.314851	0.368599	0.040*	0.892 (3)
C11B	0.697 (6)	0.273 (2)	0.3769 (19)	0.0203 (18)*	0.108 (3)
H11C	0.613084	0.281278	0.340010	0.024*	0.108 (3)
H11D	0.770694	0.320734	0.378786	0.024*	0.108 (3)
C12A	0.6733 (3)	0.28113 (17)	0.42800 (14)	0.0223 (6)	0.892 (3)
C12B	0.651 (3)	0.2870 (12)	0.4280 (12)	0.0203 (18)*	0.108 (3)
C13A	0.5515 (2)	0.3498 (3)	0.42170 (15)	0.0284 (6)	0.892 (3)
H13A	0.528888	0.344473	0.455909	0.034*	0.892 (3)
H13B	0.465152	0.330764	0.387914	0.034*	0.892 (3)
C13B	0.518 (3)	0.349 (2)	0.4150 (15)	0.0203 (18)*	0.108 (3)
H13C	0.483509	0.338398	0.445655	0.024*	0.108 (3)
H13D	0.442776	0.326030	0.378784	0.024*	0.108 (3)
C14A	0.5885 (2)	0.45441 (16)	0.41473 (9)	0.0307 (5)	0.892 (3)
H14A	0.603163	0.461269	0.378796	0.037*	0.892 (3)
H14B	0.507726	0.496456	0.412131	0.037*	0.892 (3)
C14B	0.535 (2)	0.4608 (14)	0.4093 (8)	0.0203 (18)*	0.108 (3)
H14C	0.548316	0.474167	0.373635	0.024*	0.108 (3)
H14D	0.445952	0.493368	0.406538	0.024*	0.108 (3)
C15A	0.7235 (3)	0.48558 (15)	0.46518 (8)	0.0267 (4)	0.892 (3)
H15A	0.706406	0.480777	0.501104	0.032*	0.892 (3)
C15B	0.654 (2)	0.4996 (12)	0.4572 (7)	0.0203 (18)*	0.108 (3)
H15B	0.635274	0.492084	0.492578	0.024*	0.108 (3)
C16A	0.8469 (2)	0.42084 (16)	0.47028 (8)	0.0261 (4)	0.892 (3)
H16A	0.933141	0.440372	0.503969	0.031*	0.892 (3)
H16B	0.867971	0.428206	0.435805	0.031*	0.892 (3)
C16B	0.791 (3)	0.4494 (14)	0.4659 (7)	0.0203 (18)*	0.108 (3)
H16C	0.868915	0.476239	0.500163	0.024*	0.108 (3)
H16D	0.814573	0.461434	0.432469	0.024*	0.108 (3)
C17A	0.8131 (2)	0.31553 (15)	0.47662 (9)	0.0215 (5)	0.892 (3)
H17A	0.804927	0.306878	0.513749	0.026*	0.892 (3)
H17B	0.893491	0.275115	0.477054	0.026*	0.892 (3)
C17B	0.781 (2)	0.3407 (15)	0.4737 (10)	0.0203 (18)*	0.108 (3)
H17C	0.779365	0.329361	0.511730	0.024*	0.108 (3)
H17D	0.870363	0.311012	0.474303	0.024*	0.108 (3)
C18A	0.6803 (3)	0.65329 (16)	0.46879 (12)	0.0413 (6)	0.892 (3)
H18A	0.583914	0.650527	0.438231	0.062*	0.892 (3)
H18B	0.722462	0.716483	0.468597	0.062*	0.892 (3)
H18C	0.674585	0.642820	0.505843	0.062*	0.892 (3)
C18B	0.7490 (18)	0.6576 (11)	0.4964 (7)	0.0203 (18)*	0.108 (3)
H18D	0.754713	0.724310	0.485220	0.030*	0.108 (3)
H18E	0.845719	0.630669	0.514422	0.030*	0.108 (3)
H18F	0.702936	0.655535	0.523542	0.030*	0.108 (3)
C19	0.60745 (14)	0.15389 (9)	0.60063 (6)	0.0138 (3)
C20	0.57460 (14)	0.16738 (9)	0.65227 (6)	0.0144 (3)
C21	0.43197 (15)	0.15223 (11)	0.65370 (6)	0.0188 (3)
H21A	0.398441	0.087093	0.640470	0.028*
H21B	0.363969	0.199100	0.628608	0.028*
H21C	0.439273	0.160477	0.692959	0.028*
C22	0.80075 (14)	0.20290 (10)	0.67386 (6)	0.0144 (3)
C23	0.93006 (14)	0.14103 (10)	0.70748 (6)	0.0152 (3)
C24	0.93173 (15)	0.05021 (10)	0.72998 (6)	0.0170 (3)
H24	0.845787	0.018643	0.726256	0.020*
C25	1.06528 (16)	0.00721 (11)	0.75835 (6)	0.0195 (3)
C26	1.19161 (16)	0.05226 (11)	0.76421 (6)	0.0218 (3)
H26	1.280946	0.021263	0.784060	0.026*
C27	1.18686 (15)	0.14333 (11)	0.74081 (6)	0.0201 (3)
H27	1.272763	0.174655	0.744257	0.024*
C28	1.05525 (15)	0.18787 (10)	0.71239 (6)	0.0173 (3)
C29	1.02117 (15)	0.28508 (10)	0.68463 (6)	0.0189 (3)
H29A	1.022639	0.283712	0.646033	0.023*
H29B	1.090366	0.333869	0.708176	0.023*
C30	0.86808 (14)	0.30664 (10)	0.68100 (6)	0.0158 (3)
C31	0.78163 (17)	0.37358 (10)	0.63154 (6)	0.0215 (3)
H31A	0.682777	0.379223	0.629414	0.026*
H31B	0.776406	0.345604	0.595042	0.026*
C32	0.84940 (17)	0.47367 (11)	0.63930 (6)	0.0237 (3)
H32A	0.945356	0.468505	0.638376	0.028*
H32B	0.789723	0.515270	0.607076	0.028*
C33	0.86370 (16)	0.51995 (10)	0.69566 (6)	0.0199 (3)
H33	0.766053	0.534957	0.693902	0.024*
C34	0.94019 (15)	0.45383 (10)	0.74631 (6)	0.0184 (3)
H34A	0.935315	0.482069	0.781137	0.022*
H34B	1.042379	0.449010	0.752665	0.022*
C35	0.87464 (15)	0.35300 (10)	0.73697 (6)	0.0166 (3)
H35A	0.776587	0.356845	0.735909	0.020*
H35B	0.932251	0.311634	0.769691	0.020*
C36	0.86287 (19)	0.68719 (11)	0.67521 (7)	0.0294 (4)
H36A	0.785107	0.699087	0.687764	0.044*
H36B	0.822439	0.673693	0.634040	0.044*
H36C	0.924525	0.744030	0.683035	0.044*
N1	0.50182 (12)	0.12806 (8)	0.54828 (5)	0.0145 (2)
N2	0.65823 (13)	0.16116 (9)	0.50079 (5)	0.0158 (2)
H2	0.730 (2)	0.1702 (12)	0.5305 (8)	0.019*
N3	0.48867 (13)	0.15027 (9)	0.40810 (5)	0.0197 (3)
N4	0.74130 (12)	0.17302 (8)	0.61310 (5)	0.0144 (2)
N5	0.68690 (12)	0.19542 (8)	0.69490 (5)	0.0147 (2)
O1A	0.76650 (15)	0.58132 (9)	0.45969 (6)	0.0329 (4)	0.892 (3)
O1B	0.6675 (12)	0.6029 (8)	0.4471 (4)	0.0203 (18)*	0.108 (3)
O2	0.94500 (11)	0.60694 (7)	0.70543 (5)	0.0233 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1A	0.01661 (19)	0.0563 (3)	0.0367 (2)	−0.00006 (10)	0.00794 (11)	−0.02513 (17)
Br2	0.03585 (10)	0.02105 (9)	0.02360 (9)	0.00887 (6)	0.01305 (7)	0.00352 (6)
C1	0.0141 (6)	0.0122 (6)	0.0154 (7)	−0.0012 (5)	0.0039 (5)	0.0001 (5)
C2	0.0167 (7)	0.0152 (7)	0.0149 (7)	−0.0023 (5)	0.0034 (6)	0.0001 (5)
C3	0.0160 (7)	0.0228 (7)	0.0185 (7)	−0.0044 (6)	0.0035 (6)	−0.0001 (6)
C4	0.0179 (7)	0.0278 (8)	0.0105 (6)	−0.0081 (6)	0.0039 (5)	−0.0001 (6)
C5A	0.0174 (13)	0.0380 (12)	0.0125 (8)	−0.0138 (8)	0.0075 (8)	−0.0092 (9)
C6A	0.0165 (12)	0.0382 (11)	0.0161 (8)	−0.0104 (8)	0.0078 (8)	−0.0112 (8)
C7A	0.0149 (13)	0.0498 (12)	0.0238 (10)	−0.0120 (8)	0.0078 (9)	−0.0208 (8)
C8A	0.0242 (15)	0.0683 (16)	0.0288 (11)	−0.0214 (11)	0.0189 (11)	−0.0257 (10)
C9A	0.038 (2)	0.0692 (16)	0.0227 (10)	−0.0302 (12)	0.0220 (12)	−0.0168 (10)
C10A	0.0292 (16)	0.0499 (13)	0.0153 (8)	−0.0223 (9)	0.0109 (9)	−0.0089 (9)
C11A	0.0400 (13)	0.0461 (15)	0.0131 (13)	−0.0225 (12)	0.0099 (9)	−0.0006 (11)
C12A	0.0217 (13)	0.0293 (10)	0.0141 (8)	−0.0120 (8)	0.0051 (9)	0.0022 (7)
C13A	0.0226 (14)	0.0294 (10)	0.0242 (13)	−0.0090 (12)	−0.0001 (13)	0.0075 (9)
C14A	0.0251 (10)	0.0287 (10)	0.0314 (11)	−0.0038 (10)	0.0040 (10)	0.0105 (8)
C15A	0.0267 (11)	0.0229 (10)	0.0268 (10)	−0.0069 (9)	0.0068 (9)	0.0058 (7)
C16A	0.0220 (9)	0.0262 (10)	0.0255 (10)	−0.0090 (8)	0.0046 (8)	0.0025 (7)
C17A	0.0193 (11)	0.0241 (12)	0.0177 (8)	−0.0075 (7)	0.0040 (8)	0.0014 (8)
C18A	0.0414 (13)	0.0270 (11)	0.0520 (15)	0.0018 (9)	0.0149 (12)	0.0051 (11)
C19	0.0157 (6)	0.0112 (6)	0.0143 (6)	0.0003 (5)	0.0059 (5)	0.0009 (5)
C20	0.0154 (6)	0.0130 (6)	0.0150 (6)	0.0011 (5)	0.0061 (5)	0.0003 (5)
C21	0.0150 (7)	0.0248 (7)	0.0173 (7)	−0.0013 (6)	0.0071 (6)	−0.0019 (6)
C22	0.0142 (6)	0.0172 (7)	0.0126 (6)	−0.0025 (5)	0.0060 (5)	−0.0018 (5)
C23	0.0144 (7)	0.0199 (7)	0.0113 (6)	−0.0001 (5)	0.0051 (5)	−0.0035 (5)
C24	0.0173 (7)	0.0203 (7)	0.0149 (7)	−0.0005 (5)	0.0081 (6)	−0.0023 (5)
C25	0.0240 (7)	0.0213 (7)	0.0137 (6)	0.0044 (6)	0.0080 (6)	−0.0023 (5)
C26	0.0175 (7)	0.0289 (8)	0.0171 (7)	0.0063 (6)	0.0048 (6)	−0.0061 (6)
C27	0.0143 (7)	0.0272 (8)	0.0198 (7)	−0.0022 (6)	0.0078 (6)	−0.0086 (6)
C28	0.0171 (7)	0.0214 (7)	0.0155 (7)	−0.0033 (6)	0.0087 (6)	−0.0062 (5)
C29	0.0179 (7)	0.0208 (7)	0.0213 (7)	−0.0046 (6)	0.0115 (6)	−0.0046 (6)
C30	0.0162 (7)	0.0162 (7)	0.0147 (7)	−0.0026 (5)	0.0059 (5)	−0.0018 (5)
C31	0.0262 (8)	0.0189 (7)	0.0152 (7)	−0.0035 (6)	0.0039 (6)	−0.0006 (6)
C32	0.0318 (8)	0.0190 (7)	0.0169 (7)	−0.0045 (6)	0.0062 (6)	0.0005 (6)
C33	0.0198 (7)	0.0166 (7)	0.0207 (7)	−0.0043 (5)	0.0055 (6)	−0.0021 (6)
C34	0.0188 (7)	0.0191 (7)	0.0155 (7)	−0.0016 (6)	0.0051 (6)	−0.0026 (5)
C35	0.0171 (7)	0.0177 (7)	0.0145 (7)	−0.0002 (5)	0.0058 (6)	−0.0014 (5)
C36	0.0350 (9)	0.0188 (8)	0.0263 (8)	−0.0046 (7)	0.0038 (7)	0.0016 (6)
N1	0.0144 (6)	0.0151 (6)	0.0135 (6)	−0.0013 (4)	0.0050 (5)	−0.0004 (4)
N2	0.0139 (6)	0.0221 (6)	0.0101 (5)	−0.0041 (5)	0.0033 (5)	−0.0004 (5)
N3	0.0185 (6)	0.0228 (6)	0.0149 (6)	−0.0070 (5)	0.0034 (5)	0.0003 (5)
N4	0.0145 (5)	0.0151 (5)	0.0132 (6)	−0.0011 (4)	0.0052 (5)	−0.0010 (4)
N5	0.0142 (5)	0.0152 (6)	0.0157 (6)	0.0003 (4)	0.0071 (5)	0.0002 (4)
O1A	0.0323 (9)	0.0226 (7)	0.0399 (8)	−0.0063 (6)	0.0105 (6)	0.0047 (6)
O2	0.0238 (5)	0.0174 (5)	0.0239 (5)	−0.0050 (4)	0.0045 (4)	−0.0010 (4)

Geometric parameters (Å, º)

Br1A—C7A	1.897 (2)	C16A—H16A	0.9900
Br1B—C7B	1.916 (9)	C16A—H16B	0.9900
Br2—C25	1.9043 (15)	C16A—C17A	1.529 (3)
C1—C2	1.4959 (19)	C16B—H16C	0.9900
C1—N1	1.3081 (18)	C16B—H16D	0.9900
C1—N2	1.3374 (18)	C16B—C17B	1.53 (3)
C2—C3	1.4884 (19)	C17A—H17A	0.9900
C2—N3	1.2800 (19)	C17A—H17B	0.9900
C3—H3A	0.9800	C17B—H17C	0.9900
C3—H3B	0.9800	C17B—H17D	0.9900
C3—H3C	0.9800	C18A—H18A	0.9800
C4—C5A	1.530 (3)	C18A—H18B	0.9800
C4—C5B	1.370 (18)	C18A—H18C	0.9800
C4—C12A	1.572 (3)	C18A—O1A	1.411 (3)
C4—C12B	1.597 (18)	C18B—H18D	0.9800
C4—N2	1.4509 (17)	C18B—H18E	0.9800
C4—N3	1.4759 (18)	C18B—H18F	0.9800
C5A—C6A	1.375 (3)	C18B—O1B	1.418 (19)
C5A—C10A	1.395 (2)	C19—C20	1.4940 (18)
C5B—C6B	1.3900	C19—N1	1.3853 (18)
C5B—C10B	1.3900	C19—N4	1.2983 (18)
C6B—H6B	0.9500	C20—C21	1.4833 (19)
C6B—C7B	1.3900	C20—N5	1.2837 (18)
C7B—C8B	1.3900	C21—H21A	0.9800
C8B—H8B	0.9500	C21—H21B	0.9800
C8B—C9B	1.3900	C21—H21C	0.9800
C9B—H9B	0.9500	C22—C23	1.5196 (19)
C9B—C10B	1.3900	C22—C30	1.5778 (18)
C10B—C11B	1.516 (17)	C22—N4	1.4791 (17)
C6A—H6A	0.9500	C22—N5	1.4635 (17)
C6A—C7A	1.390 (2)	C23—C24	1.386 (2)
C7A—C8A	1.384 (3)	C23—C28	1.3930 (19)
C8A—H8A	0.9500	C24—H24	0.9500
C8A—C9A	1.379 (3)	C24—C25	1.395 (2)
C9A—H9A	0.9500	C25—C26	1.385 (2)
C9A—C10A	1.397 (3)	C26—H26	0.9500
C10A—C11A	1.496 (4)	C26—C27	1.394 (2)
C11A—H11A	0.9900	C27—H27	0.9500
C11A—H11B	0.9900	C27—C28	1.389 (2)
C11A—C12A	1.557 (3)	C28—C29	1.502 (2)
C11B—H11C	0.9900	C29—H29A	0.9900
C11B—H11D	0.9900	C29—H29B	0.9900
C11B—C12B	1.558 (18)	C29—C30	1.5544 (19)
C12A—C13A	1.523 (3)	C30—C31	1.531 (2)
C12A—C17A	1.543 (3)	C30—C35	1.5427 (18)
C12B—C13B	1.531 (18)	C31—H31A	0.9900
C12B—C17B	1.560 (18)	C31—H31B	0.9900
C13A—H13A	0.9900	C31—C32	1.532 (2)
C13A—H13B	0.9900	C32—H32A	0.9900
C13A—C14A	1.532 (4)	C32—H32B	0.9900
C13B—H13C	0.9900	C32—C33	1.527 (2)
C13B—H13D	0.9900	C33—H33	1.0000
C13B—C14B	1.58 (4)	C33—C34	1.522 (2)
C14A—H14A	0.9900	C33—O2	1.4318 (17)
C14A—H14B	0.9900	C34—H34A	0.9900
C14A—C15A	1.523 (3)	C34—H34B	0.9900
C14B—H14C	0.9900	C34—C35	1.5316 (19)
C14B—H14D	0.9900	C35—H35A	0.9900
C14B—C15B	1.44 (2)	C35—H35B	0.9900
C15A—H15A	1.0000	C36—H36A	0.9800
C15A—C16A	1.510 (3)	C36—H36B	0.9800
C15A—O1A	1.427 (2)	C36—H36C	0.9800
C15B—H15B	1.0000	C36—O2	1.4232 (19)
C15B—C16B	1.49 (3)	N2—H2	0.826 (19)
C15B—O1B	1.477 (19)
N1—C1—C2	125.21 (12)	C15B—C16B—H16C	109.1
N1—C1—N2	130.25 (13)	C15B—C16B—H16D	109.1
N2—C1—C2	104.43 (12)	C15B—C16B—C17B	112.3 (16)
C3—C2—C1	123.63 (12)	H16C—C16B—H16D	107.9
N3—C2—C1	111.73 (12)	C17B—C16B—H16C	109.1
N3—C2—C3	124.63 (13)	C17B—C16B—H16D	109.1
C2—C3—H3A	109.5	C12A—C17A—H17A	109.0
C2—C3—H3B	109.5	C12A—C17A—H17B	109.0
C2—C3—H3C	109.5	C16A—C17A—C12A	112.77 (17)
H3A—C3—H3B	109.5	C16A—C17A—H17A	109.0
H3A—C3—H3C	109.5	C16A—C17A—H17B	109.0
H3B—C3—H3C	109.5	H17A—C17A—H17B	107.8
C5A—C4—C12A	101.9 (2)	C12B—C17B—H17C	108.1
C5B—C4—C12B	109.6 (18)	C12B—C17B—H17D	108.1
C5B—C4—N2	115.9 (15)	C16B—C17B—C12B	116.9 (16)
C5B—C4—N3	109 (2)	C16B—C17B—H17C	108.1
N2—C4—C5A	115.42 (19)	C16B—C17B—H17D	108.1
N2—C4—C12A	114.73 (16)	H17C—C17B—H17D	107.3
N2—C4—C12B	112.3 (10)	H18A—C18A—H18B	109.5
N2—C4—N3	104.06 (11)	H18A—C18A—H18C	109.5
N3—C4—C5A	109.3 (2)	H18B—C18A—H18C	109.5
N3—C4—C12A	111.57 (14)	O1A—C18A—H18A	109.5
N3—C4—C12B	105.2 (9)	O1A—C18A—H18B	109.5
C6A—C5A—C4	127.7 (2)	O1A—C18A—H18C	109.5
C6A—C5A—C10A	123.04 (17)	H18D—C18B—H18E	109.5
C10A—C5A—C4	109.2 (2)	H18D—C18B—H18F	109.5
C4—C5B—C6B	129.4 (15)	H18E—C18B—H18F	109.5
C4—C5B—C10B	110.6 (15)	O1B—C18B—H18D	109.5
C6B—C5B—C10B	120.0	O1B—C18B—H18E	109.5
C5B—C6B—H6B	120.0	O1B—C18B—H18F	109.5
C5B—C6B—C7B	120.0	N1—C19—C20	121.30 (12)
C7B—C6B—H6B	120.0	N4—C19—C20	110.01 (12)
C6B—C7B—Br1B	119.7 (7)	N4—C19—N1	128.65 (12)
C6B—C7B—C8B	120.0	C21—C20—C19	124.80 (12)
C8B—C7B—Br1B	120.3 (7)	N5—C20—C19	110.24 (12)
C7B—C8B—H8B	120.0	N5—C20—C21	124.96 (12)
C9B—C8B—C7B	120.0	C20—C21—H21A	109.5
C9B—C8B—H8B	120.0	C20—C21—H21B	109.5
C8B—C9B—H9B	120.0	C20—C21—H21C	109.5
C8B—C9B—C10B	120.0	H21A—C21—H21B	109.5
C10B—C9B—H9B	120.0	H21A—C21—H21C	109.5
C5B—C10B—C11B	109.3 (18)	H21B—C21—H21C	109.5
C9B—C10B—C5B	120.0	C23—C22—C30	102.40 (11)
C9B—C10B—C11B	130.5 (19)	N4—C22—C23	109.30 (11)
C5A—C6A—H6A	121.8	N4—C22—C30	110.81 (10)
C5A—C6A—C7A	116.49 (17)	N5—C22—C23	112.87 (11)
C7A—C6A—H6A	121.8	N5—C22—C30	113.26 (11)
C6A—C7A—Br1A	118.23 (17)	N5—C22—N4	108.11 (10)
C8A—C7A—Br1A	119.18 (18)	C24—C23—C22	127.95 (12)
C8A—C7A—C6A	122.6 (2)	C24—C23—C28	122.05 (13)
C7A—C8A—H8A	120.2	C28—C23—C22	109.99 (12)
C9A—C8A—C7A	119.57 (18)	C23—C24—H24	121.5
C9A—C8A—H8A	120.2	C23—C24—C25	117.00 (13)
C8A—C9A—H9A	120.1	C25—C24—H24	121.5
C8A—C9A—C10A	119.84 (19)	C24—C25—Br2	118.46 (11)
C10A—C9A—H9A	120.1	C26—C25—Br2	119.30 (11)
C5A—C10A—C9A	118.5 (2)	C26—C25—C24	122.24 (14)
C5A—C10A—C11A	110.7 (3)	C25—C26—H26	120.2
C9A—C10A—C11A	130.8 (3)	C25—C26—C27	119.60 (13)
C10A—C11A—H11A	111.1	C27—C26—H26	120.2
C10A—C11A—H11B	111.1	C26—C27—H27	120.3
C10A—C11A—C12A	103.2 (3)	C28—C27—C26	119.34 (13)
H11A—C11A—H11B	109.1	C28—C27—H27	120.3
C12A—C11A—H11A	111.1	C23—C28—C29	110.39 (12)
C12A—C11A—H11B	111.1	C27—C28—C23	119.76 (14)
C10B—C11B—H11C	110.5	C27—C28—C29	129.84 (13)
C10B—C11B—H11D	110.5	C28—C29—H29A	111.0
C10B—C11B—C12B	106.1 (18)	C28—C29—H29B	111.0
H11C—C11B—H11D	108.7	C28—C29—C30	103.86 (11)
C12B—C11B—H11C	110.5	H29A—C29—H29B	109.0
C12B—C11B—H11D	110.5	C30—C29—H29A	111.0
C11A—C12A—C4	101.9 (2)	C30—C29—H29B	111.0
C13A—C12A—C4	111.3 (2)	C29—C30—C22	102.12 (11)
C13A—C12A—C11A	115.1 (3)	C31—C30—C22	112.43 (11)
C13A—C12A—C17A	110.0 (2)	C31—C30—C29	113.56 (12)
C17A—C12A—C4	108.8 (2)	C31—C30—C35	107.73 (11)
C17A—C12A—C11A	109.5 (3)	C35—C30—C22	110.21 (11)
C11B—C12B—C4	98.0 (15)	C35—C30—C29	110.76 (11)
C11B—C12B—C17B	104 (3)	C30—C31—H31A	109.3
C13B—C12B—C4	117 (2)	C30—C31—H31B	109.3
C13B—C12B—C11B	115 (2)	C30—C31—C32	111.46 (12)
C13B—C12B—C17B	107.8 (18)	H31A—C31—H31B	108.0
C17B—C12B—C4	114.4 (18)	C32—C31—H31A	109.3
C12A—C13A—H13A	109.1	C32—C31—H31B	109.3
C12A—C13A—H13B	109.1	C31—C32—H32A	109.2
C12A—C13A—C14A	112.4 (2)	C31—C32—H32B	109.2
H13A—C13A—H13B	107.9	H32A—C32—H32B	107.9
C14A—C13A—H13A	109.1	C33—C32—C31	111.93 (12)
C14A—C13A—H13B	109.1	C33—C32—H32A	109.2
C12B—C13B—H13C	108.0	C33—C32—H32B	109.2
C12B—C13B—H13D	108.0	C32—C33—H33	109.1
C12B—C13B—C14B	117 (2)	C34—C33—C32	111.51 (12)
H13C—C13B—H13D	107.2	C34—C33—H33	109.1
C14B—C13B—H13C	108.0	O2—C33—C32	110.57 (12)
C14B—C13B—H13D	108.0	O2—C33—H33	109.1
C13A—C14A—H14A	109.5	O2—C33—C34	107.43 (11)
C13A—C14A—H14B	109.5	C33—C34—H34A	109.2
H14A—C14A—H14B	108.1	C33—C34—H34B	109.2
C15A—C14A—C13A	110.71 (17)	C33—C34—C35	112.26 (11)
C15A—C14A—H14A	109.5	H34A—C34—H34B	107.9
C15A—C14A—H14B	109.5	C35—C34—H34A	109.2
C13B—C14B—H14C	109.2	C35—C34—H34B	109.2
C13B—C14B—H14D	109.2	C30—C35—H35A	109.1
H14C—C14B—H14D	107.9	C30—C35—H35B	109.1
C15B—C14B—C13B	112.1 (18)	C34—C35—C30	112.46 (11)
C15B—C14B—H14C	109.2	C34—C35—H35A	109.1
C15B—C14B—H14D	109.2	C34—C35—H35B	109.1
C14A—C15A—H15A	109.0	H35A—C35—H35B	107.8
C16A—C15A—C14A	110.03 (18)	H36A—C36—H36B	109.5
C16A—C15A—H15A	109.0	H36A—C36—H36C	109.5
O1A—C15A—C14A	113.11 (17)	H36B—C36—H36C	109.5
O1A—C15A—H15A	109.0	O2—C36—H36A	109.5
O1A—C15A—C16A	106.73 (18)	O2—C36—H36B	109.5
C14B—C15B—H15B	108.8	O2—C36—H36C	109.5
C14B—C15B—C16B	111.8 (14)	C1—N1—C19	116.17 (12)
C14B—C15B—O1B	108.8 (14)	C1—N2—C4	111.11 (12)
C16B—C15B—H15B	108.8	C1—N2—H2	119.9 (12)
O1B—C15B—H15B	108.8	C4—N2—H2	128.8 (12)
O1B—C15B—C16B	109.8 (13)	C2—N3—C4	108.41 (12)
C15A—C16A—H16A	109.3	C19—N4—C22	105.32 (11)
C15A—C16A—H16B	109.3	C20—N5—C22	106.28 (11)
C15A—C16A—C17A	111.51 (16)	C18A—O1A—C15A	114.26 (18)
H16A—C16A—H16B	108.0	C18B—O1B—C15B	115.5 (11)
C17A—C16A—H16A	109.3	C36—O2—C33	113.31 (11)
C17A—C16A—H16B	109.3
Br1A—C7A—C8A—C9A	179.2 (4)	C22—C23—C24—C25	178.69 (13)
Br1B—C7B—C8B—C9B	−178 (3)	C22—C23—C28—C27	−178.89 (12)
Br2—C25—C26—C27	178.87 (10)	C22—C23—C28—C29	1.91 (15)
C1—C2—N3—C4	1.44 (16)	C22—C30—C31—C32	−179.77 (12)
C2—C1—N1—C19	−170.60 (12)	C22—C30—C35—C34	179.62 (11)
C2—C1—N2—C4	5.17 (15)	C23—C22—C30—C29	31.83 (12)
C3—C2—N3—C4	−179.96 (13)	C23—C22—C30—C31	153.90 (11)
C4—C5A—C6A—C7A	−179.2 (5)	C23—C22—C30—C35	−85.90 (12)
C4—C5A—C10A—C9A	−180.0 (4)	C23—C22—N4—C19	125.11 (12)
C4—C5A—C10A—C11A	1.7 (5)	C23—C22—N5—C20	−122.43 (12)
C4—C5B—C6B—C7B	178 (5)	C23—C24—C25—Br2	−179.34 (10)
C4—C5B—C10B—C9B	−179 (4)	C23—C24—C25—C26	0.1 (2)
C4—C5B—C10B—C11B	7 (4)	C23—C28—C29—C30	19.18 (14)
C4—C12A—C13A—C14A	173.7 (2)	C24—C23—C28—C27	−0.3 (2)
C4—C12A—C17A—C16A	−173.89 (18)	C24—C23—C28—C29	−179.47 (12)
C4—C12B—C13B—C14B	172 (2)	C24—C25—C26—C27	−0.5 (2)
C4—C12B—C17B—C16B	−174.2 (17)	C25—C26—C27—C28	0.6 (2)
C5A—C4—C12A—C11A	34.2 (4)	C26—C27—C28—C23	−0.2 (2)
C5A—C4—C12A—C13A	157.4 (3)	C26—C27—C28—C29	178.82 (13)
C5A—C4—C12A—C17A	−81.3 (3)	C27—C28—C29—C30	−159.92 (14)
C5A—C4—N2—C1	−124.3 (3)	C28—C23—C24—C25	0.3 (2)
C5A—C4—N3—C2	125.48 (18)	C28—C29—C30—C22	−31.12 (13)
C5A—C6A—C7A—Br1A	−179.6 (4)	C28—C29—C30—C31	−152.41 (11)
C5A—C6A—C7A—C8A	−1.2 (2)	C28—C29—C30—C35	86.22 (13)
C5A—C10A—C11A—C12A	20.8 (5)	C29—C30—C31—C32	−64.44 (16)
C5B—C4—C12B—C11B	25 (3)	C29—C30—C35—C34	67.36 (15)
C5B—C4—C12B—C13B	149 (3)	C30—C22—C23—C24	159.75 (13)
C5B—C4—C12B—C17B	−84 (3)	C30—C22—C23—C28	−21.74 (14)
C5B—C4—N2—C1	−124 (2)	C30—C22—N4—C19	−122.77 (12)
C5B—C4—N3—C2	125.9 (11)	C30—C22—N5—C20	121.78 (12)
C5B—C6B—C7B—Br1B	178 (3)	C30—C31—C32—C33	−57.70 (17)
C5B—C6B—C7B—C8B	0.0	C31—C30—C35—C34	−57.38 (15)
C5B—C10B—C11B—C12B	10 (4)	C31—C32—C33—C34	52.46 (17)
C6B—C5B—C10B—C9B	0.0	C31—C32—C33—O2	171.92 (12)
C6B—C5B—C10B—C11B	−175 (4)	C32—C33—C34—C35	−50.88 (16)
C6B—C7B—C8B—C9B	0.0	C32—C33—O2—C36	81.23 (16)
C7B—C8B—C9B—C10B	0.0	C33—C34—C35—C30	54.70 (16)
C8B—C9B—C10B—C5B	0.0	C34—C33—O2—C36	−156.88 (12)
C8B—C9B—C10B—C11B	174 (5)	C35—C30—C31—C32	58.61 (16)
C9B—C10B—C11B—C12B	−164 (3)	N1—C1—C2—C3	−6.3 (2)
C10B—C5B—C6B—C7B	0.0	N1—C1—C2—N3	172.30 (13)
C10B—C11B—C12B—C4	−20 (4)	N1—C1—N2—C4	−171.09 (14)
C10B—C11B—C12B—C13B	−145 (3)	N1—C19—C20—C21	2.0 (2)
C10B—C11B—C12B—C17B	98 (4)	N1—C19—C20—N5	−176.99 (12)
C6A—C5A—C10A—C9A	0.1 (3)	N1—C19—N4—C22	175.98 (13)
C6A—C5A—C10A—C11A	−178.3 (5)	N2—C1—C2—C3	177.18 (13)
C6A—C7A—C8A—C9A	0.7 (3)	N2—C1—C2—N3	−4.21 (16)
C7A—C8A—C9A—C10A	0.2 (3)	N2—C1—N1—C19	5.0 (2)
C8A—C9A—C10A—C5A	−0.6 (3)	N2—C4—C5A—C6A	31.9 (4)
C8A—C9A—C10A—C11A	177.4 (6)	N2—C4—C5A—C10A	−148.1 (2)
C9A—C10A—C11A—C12A	−157.3 (4)	N2—C4—C5B—C6B	32 (4)
C10A—C5A—C6A—C7A	0.8 (2)	N2—C4—C5B—C10B	−149.3 (17)
C10A—C11A—C12A—C4	−33.7 (5)	N2—C4—C12A—C11A	159.7 (3)
C10A—C11A—C12A—C13A	−154.2 (4)	N2—C4—C12A—C13A	−77.2 (3)
C10A—C11A—C12A—C17A	81.4 (4)	N2—C4—C12A—C17A	44.1 (2)
C11A—C12A—C13A—C14A	−71.1 (4)	N2—C4—C12B—C11B	156 (2)
C11A—C12A—C17A—C16A	75.6 (2)	N2—C4—C12B—C13B	−81 (2)
C11B—C12B—C13B—C14B	−74 (3)	N2—C4—C12B—C17B	46 (2)
C11B—C12B—C17B—C16B	80 (2)	N2—C4—N3—C2	1.64 (16)
C12A—C4—C5A—C6A	156.9 (3)	N3—C4—C5A—C6A	−85.0 (4)
C12A—C4—C5A—C10A	−23.1 (3)	N3—C4—C5A—C10A	95.0 (3)
C12A—C4—N2—C1	117.70 (15)	N3—C4—C5B—C6B	−85 (3)
C12A—C4—N3—C2	−122.61 (16)	N3—C4—C5B—C10B	94 (2)
C12A—C13A—C14A—C15A	−57.2 (3)	N3—C4—C12A—C11A	−82.3 (3)
C12B—C4—C5B—C6B	161 (3)	N3—C4—C12A—C13A	40.8 (3)
C12B—C4—C5B—C10B	−21 (3)	N3—C4—C12A—C17A	162.13 (15)
C12B—C4—N2—C1	108.8 (10)	N3—C4—C12B—C11B	−92 (2)
C12B—C4—N3—C2	−116.6 (11)	N3—C4—C12B—C13B	31 (2)
C12B—C13B—C14B—C15B	−51 (3)	N3—C4—C12B—C17B	159.0 (16)
C13A—C12A—C17A—C16A	−51.7 (3)	N3—C4—N2—C1	−4.47 (16)
C13A—C14A—C15A—C16A	58.1 (3)	N4—C19—C20—C21	179.78 (13)
C13A—C14A—C15A—O1A	177.4 (2)	N4—C19—C20—N5	0.82 (16)
C13B—C12B—C17B—C16B	−42 (3)	N4—C19—N1—C1	−10.6 (2)
C13B—C14B—C15B—C16B	55 (2)	N4—C22—C23—C24	−82.71 (16)
C13B—C14B—C15B—O1B	176.8 (17)	N4—C22—C23—C28	95.80 (13)
C14A—C15A—C16A—C17A	−57.1 (2)	N4—C22—C30—C29	−84.63 (12)
C14A—C15A—O1A—C18A	74.0 (3)	N4—C22—C30—C31	37.44 (15)
C14B—C15B—C16B—C17B	−56 (2)	N4—C22—C30—C35	157.64 (11)
C14B—C15B—O1B—C18B	161.4 (13)	N4—C22—N5—C20	−1.40 (14)
C15A—C16A—C17A—C12A	54.7 (2)	N5—C22—C23—C24	37.64 (19)
C15B—C16B—C17B—C12B	51 (2)	N5—C22—C23—C28	−143.85 (12)
C16A—C15A—O1A—C18A	−164.90 (18)	N5—C22—C30—C29	153.68 (11)
C16B—C15B—O1B—C18B	−75.9 (16)	N5—C22—C30—C31	−84.25 (14)
C17A—C12A—C13A—C14A	53.0 (3)	N5—C22—C30—C35	35.95 (15)
C17B—C12B—C13B—C14B	41 (3)	N5—C22—N4—C19	1.89 (14)
C19—C20—N5—C22	0.43 (14)	O1A—C15A—C16A—C17A	179.84 (15)
C20—C19—N1—C1	166.76 (12)	O1B—C15B—C16B—C17B	−177.2 (14)
C20—C19—N4—C22	−1.62 (14)	O2—C33—C34—C35	−172.18 (11)
C21—C20—N5—C22	−178.53 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N4	0.826 (19)	2.064 (18)	2.6456 (16)	127.2 (15)

(R,S)/(S,R)-(1r,1'S,4S,E)-6'-Bromo-N-[(1r,1'S,4S)-6'-bromo-4-methoxy-4''-methyl-3'H-dispiro[cyclohexane-1,2'-indene-1',2''-imidazol-5''-yl]-4-methoxy-4''-methyl-3'H-dispiro[cyclohexane-1,2'-indene-1',2''-imidazol]-5''-imine (1)

Crystal data

C36H41Br2N5O2	F(000) = 1512
Mr = 735.56	Dx = 1.424 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
a = 13.19297 (6) Å	Cell parameters from 74158 reflections
b = 17.60010 (8) Å	θ = 2.5–70.4°
c = 15.25349 (8) Å	µ = 3.30 mm^−1
β = 104.4018 (5)°	T = 100 K
V = 3430.52 (3) Å^3	Block, colourless
Z = 4	0.31 × 0.07 × 0.05 mm

Data collection

Rigaku 007HF equipped with Varimax confocal mirrors and an AFC11 goniometer and HyPix 6000 detector diffractometer	6285 independent reflections
Radiation source: Rotating anode, Rigaku 007 HF	6257 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.023
Detector resolution: 10 pixels mm^-1	θmax = 68.3°, θmin = 3.9°
profile data from ω–scans	h = −15→15
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2019)	k = −21→21
Tmin = 0.654, Tmax = 1.000	l = −18→18
97773 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.024	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.057	w = 1/[σ^2(Fo^2) + (0.0248P)^2 + 2.9185P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
6285 reflections	Δρmax = 0.33 e Å^−3
413 parameters	Δρmin = −0.44 e Å^−3
1 restraint

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.

Refinement. This diastereoisomer has crystallised in the centrosymmetric space group P2₁/n; meaning that both SS and RR forms of the API must be present in equal amounts within the crystal.

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

	x	y	z	Uiso*/Ueq
Br1	0.57538 (2)	0.34738 (2)	0.89948 (2)	0.02177 (5)
Br2	0.14814 (2)	0.66375 (2)	0.24065 (2)	0.02990 (6)
C1	0.15668 (11)	0.50387 (8)	0.69473 (9)	0.0129 (3)
C2	0.13914 (11)	0.52942 (8)	0.78320 (10)	0.0144 (3)
C3	0.04172 (12)	0.51294 (10)	0.81180 (11)	0.0214 (3)
H3A	0.048466	0.532334	0.873213	0.032*
H3B	0.030082	0.457923	0.810962	0.032*
H3C	−0.017676	0.537693	0.770109	0.032*
C4	0.29513 (11)	0.57251 (8)	0.77417 (9)	0.0133 (3)
C5	0.39917 (11)	0.54110 (8)	0.82716 (9)	0.0140 (3)
C6	0.43135 (12)	0.46632 (9)	0.83361 (10)	0.0162 (3)
H6	0.388386	0.427279	0.800815	0.019*
C7	0.52897 (12)	0.45036 (9)	0.88989 (10)	0.0173 (3)
C8	0.59218 (12)	0.50677 (9)	0.93894 (10)	0.0185 (3)
H8	0.657774	0.494104	0.978454	0.022*
C9	0.55861 (12)	0.58207 (9)	0.92970 (10)	0.0176 (3)
H9	0.601620	0.621205	0.962229	0.021*
C10	0.46163 (12)	0.59959 (9)	0.87251 (10)	0.0157 (3)
C11	0.40713 (12)	0.67508 (9)	0.84824 (10)	0.0175 (3)
H11A	0.456675	0.714295	0.837849	0.021*
H11B	0.374767	0.692667	0.896646	0.021*
C12	0.32230 (11)	0.65767 (8)	0.75962 (10)	0.0136 (3)
C13	0.22456 (11)	0.70763 (8)	0.74388 (11)	0.0174 (3)
H13A	0.168199	0.684004	0.696541	0.021*
H13B	0.200517	0.709635	0.800360	0.021*
C14	0.24256 (13)	0.78862 (9)	0.71501 (13)	0.0251 (4)
H14A	0.175330	0.816570	0.701148	0.030*
H14B	0.291377	0.814993	0.765677	0.030*
C15	0.28730 (12)	0.78963 (9)	0.63259 (12)	0.0217 (3)
H15	0.236081	0.765257	0.580750	0.026*
C16	0.38937 (12)	0.74506 (8)	0.65217 (11)	0.0177 (3)
H16A	0.441114	0.769143	0.702812	0.021*
H16B	0.418255	0.745545	0.598164	0.021*
C17	0.36986 (11)	0.66312 (8)	0.67692 (10)	0.0145 (3)
H17A	0.436898	0.634951	0.690158	0.017*
H17B	0.321797	0.638505	0.624337	0.017*
C18	0.33503 (15)	0.87778 (11)	0.53124 (14)	0.0355 (4)
H18A	0.294890	0.844671	0.483397	0.053*
H18B	0.409455	0.864737	0.543539	0.053*
H18C	0.325097	0.930878	0.511642	0.053*
C19	0.12763 (11)	0.43884 (8)	0.56219 (9)	0.0124 (3)
C20	0.07361 (11)	0.38220 (8)	0.49353 (9)	0.0123 (3)
C21	−0.02914 (11)	0.34673 (8)	0.49334 (10)	0.0159 (3)
H21A	−0.085343	0.383654	0.471467	0.024*
H21B	−0.029155	0.330987	0.554960	0.024*
H21C	−0.040429	0.302236	0.453450	0.024*
C22	0.22276 (11)	0.41636 (8)	0.46271 (9)	0.0117 (3)
C23	0.23216 (11)	0.46484 (8)	0.38289 (9)	0.0123 (3)
C24	0.18603 (11)	0.53442 (8)	0.35623 (10)	0.0158 (3)
H24	0.141328	0.558250	0.388096	0.019*
C25	0.20823 (11)	0.56779 (9)	0.28060 (11)	0.0189 (3)
C26	0.27239 (12)	0.53353 (10)	0.23273 (11)	0.0212 (3)
H26	0.285223	0.557722	0.180869	0.025*
C27	0.31778 (12)	0.46373 (9)	0.26092 (10)	0.0196 (3)
H27	0.362047	0.439791	0.228716	0.023*
C28	0.29774 (11)	0.42925 (8)	0.33682 (9)	0.0138 (3)
C29	0.33843 (11)	0.35584 (8)	0.38287 (10)	0.0144 (3)
H29A	0.412775	0.347934	0.383041	0.017*
H29B	0.296824	0.312047	0.352846	0.017*
C30	0.32551 (11)	0.36684 (8)	0.48025 (9)	0.0118 (3)
C31	0.31641 (12)	0.29247 (8)	0.52930 (10)	0.0166 (3)
H31A	0.260115	0.261062	0.491214	0.020*
H31B	0.296945	0.303725	0.586573	0.020*
C32	0.41931 (12)	0.24756 (9)	0.55019 (11)	0.0196 (3)
H32A	0.411332	0.201096	0.584435	0.023*
H32B	0.435041	0.231742	0.492700	0.023*
C33	0.51027 (12)	0.29466 (9)	0.60523 (11)	0.0219 (3)
H33	0.497643	0.305715	0.665943	0.026*
C34	0.52114 (12)	0.36922 (9)	0.55827 (11)	0.0189 (3)
H34A	0.541834	0.358860	0.501331	0.023*
H34B	0.576778	0.400299	0.597697	0.023*
C35	0.41793 (11)	0.41339 (8)	0.53713 (10)	0.0152 (3)
H35A	0.426159	0.460335	0.503813	0.018*
H35B	0.401738	0.428523	0.594668	0.018*
C36	0.62272 (17)	0.19682 (12)	0.68103 (15)	0.0448 (5)
H36A	0.573730	0.155573	0.657157	0.067*
H36B	0.609719	0.215570	0.737741	0.067*
H36C	0.694655	0.177843	0.692376	0.067*
N1	0.09138 (9)	0.46044 (7)	0.63455 (8)	0.0131 (2)
N2	0.24915 (9)	0.53150 (7)	0.69163 (8)	0.0122 (2)
H2	0.2733 (13)	0.5217 (10)	0.6481 (11)	0.015*
N3	0.21762 (9)	0.56719 (7)	0.82906 (8)	0.0151 (3)
N4	0.21425 (9)	0.45973 (7)	0.54149 (8)	0.0124 (2)
N5	0.12793 (9)	0.36819 (7)	0.43652 (8)	0.0130 (2)
O1	0.29971 (10)	0.86771 (7)	0.61123 (9)	0.0308 (3)
O2	0.60841 (9)	0.25660 (7)	0.61737 (8)	0.0303 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02290 (9)	0.01996 (9)	0.02374 (9)	0.00478 (6)	0.00824 (7)	0.00669 (6)
Br2	0.02056 (9)	0.02260 (10)	0.04550 (12)	0.00515 (7)	0.00627 (8)	0.01708 (8)
C1	0.0132 (7)	0.0124 (7)	0.0139 (7)	0.0012 (5)	0.0048 (5)	−0.0003 (5)
C2	0.0155 (7)	0.0142 (7)	0.0147 (7)	0.0000 (5)	0.0063 (6)	−0.0019 (5)
C3	0.0190 (8)	0.0274 (8)	0.0211 (8)	−0.0053 (6)	0.0113 (6)	−0.0069 (7)
C4	0.0136 (7)	0.0146 (7)	0.0124 (7)	−0.0023 (5)	0.0047 (5)	−0.0039 (5)
C5	0.0144 (7)	0.0169 (7)	0.0117 (6)	−0.0030 (6)	0.0051 (5)	−0.0012 (5)
C6	0.0175 (7)	0.0166 (7)	0.0154 (7)	−0.0039 (6)	0.0056 (6)	−0.0005 (6)
C7	0.0187 (7)	0.0196 (8)	0.0159 (7)	0.0004 (6)	0.0086 (6)	0.0035 (6)
C8	0.0137 (7)	0.0288 (8)	0.0136 (7)	−0.0005 (6)	0.0046 (6)	0.0023 (6)
C9	0.0163 (7)	0.0232 (8)	0.0137 (7)	−0.0057 (6)	0.0045 (6)	−0.0030 (6)
C10	0.0167 (7)	0.0184 (7)	0.0130 (7)	−0.0037 (6)	0.0056 (6)	−0.0025 (6)
C11	0.0183 (7)	0.0163 (7)	0.0168 (7)	−0.0038 (6)	0.0026 (6)	−0.0059 (6)
C12	0.0139 (7)	0.0121 (7)	0.0153 (7)	−0.0013 (5)	0.0044 (6)	−0.0039 (5)
C13	0.0152 (7)	0.0157 (7)	0.0229 (7)	0.0009 (6)	0.0078 (6)	−0.0045 (6)
C14	0.0223 (8)	0.0148 (8)	0.0410 (10)	0.0037 (6)	0.0129 (7)	−0.0023 (7)
C15	0.0190 (8)	0.0123 (7)	0.0334 (9)	0.0004 (6)	0.0057 (7)	0.0040 (6)
C16	0.0165 (7)	0.0137 (7)	0.0237 (8)	−0.0008 (6)	0.0068 (6)	0.0007 (6)
C17	0.0144 (7)	0.0132 (7)	0.0171 (7)	0.0007 (5)	0.0062 (6)	−0.0012 (5)
C18	0.0284 (9)	0.0273 (10)	0.0515 (12)	0.0043 (8)	0.0111 (8)	0.0194 (9)
C19	0.0114 (7)	0.0118 (7)	0.0135 (7)	−0.0003 (5)	0.0020 (5)	0.0002 (5)
C20	0.0121 (7)	0.0122 (7)	0.0122 (6)	−0.0002 (5)	0.0021 (5)	0.0004 (5)
C21	0.0124 (7)	0.0169 (7)	0.0183 (7)	−0.0033 (6)	0.0040 (6)	−0.0031 (6)
C22	0.0119 (7)	0.0129 (7)	0.0106 (6)	−0.0026 (5)	0.0032 (5)	−0.0029 (5)
C23	0.0100 (6)	0.0149 (7)	0.0114 (6)	−0.0030 (5)	0.0014 (5)	−0.0005 (5)
C24	0.0109 (7)	0.0174 (7)	0.0190 (7)	−0.0005 (6)	0.0033 (6)	−0.0003 (6)
C25	0.0113 (7)	0.0187 (8)	0.0245 (8)	−0.0005 (6)	0.0005 (6)	0.0061 (6)
C26	0.0171 (7)	0.0278 (9)	0.0193 (7)	−0.0013 (6)	0.0055 (6)	0.0090 (6)
C27	0.0177 (7)	0.0271 (8)	0.0155 (7)	0.0024 (6)	0.0072 (6)	0.0024 (6)
C28	0.0128 (7)	0.0165 (7)	0.0117 (6)	−0.0011 (5)	0.0025 (5)	−0.0006 (5)
C29	0.0158 (7)	0.0157 (7)	0.0127 (7)	0.0015 (6)	0.0050 (5)	−0.0011 (5)
C30	0.0120 (7)	0.0122 (7)	0.0114 (6)	−0.0005 (5)	0.0033 (5)	−0.0004 (5)
C31	0.0183 (7)	0.0153 (7)	0.0171 (7)	−0.0015 (6)	0.0059 (6)	0.0021 (6)
C32	0.0223 (8)	0.0158 (7)	0.0204 (7)	0.0020 (6)	0.0050 (6)	0.0051 (6)
C33	0.0211 (8)	0.0235 (8)	0.0184 (7)	0.0055 (6)	−0.0002 (6)	0.0026 (6)
C34	0.0137 (7)	0.0205 (8)	0.0202 (7)	−0.0003 (6)	−0.0001 (6)	−0.0012 (6)
C35	0.0138 (7)	0.0153 (7)	0.0154 (7)	−0.0013 (6)	0.0017 (5)	−0.0018 (6)
C36	0.0391 (11)	0.0338 (11)	0.0487 (12)	0.0068 (9)	−0.0132 (9)	0.0160 (9)
N1	0.0121 (6)	0.0147 (6)	0.0133 (6)	−0.0017 (5)	0.0047 (5)	−0.0032 (5)
N2	0.0123 (6)	0.0135 (6)	0.0119 (6)	−0.0016 (5)	0.0050 (5)	−0.0042 (5)
N3	0.0166 (6)	0.0160 (6)	0.0144 (6)	−0.0010 (5)	0.0068 (5)	−0.0025 (5)
N4	0.0129 (6)	0.0133 (6)	0.0119 (6)	−0.0009 (5)	0.0046 (5)	−0.0021 (5)
N5	0.0112 (6)	0.0140 (6)	0.0130 (6)	−0.0023 (5)	0.0016 (5)	−0.0003 (5)
O1	0.0299 (6)	0.0148 (6)	0.0502 (8)	0.0034 (5)	0.0149 (6)	0.0090 (5)
O2	0.0235 (6)	0.0282 (7)	0.0333 (7)	0.0095 (5)	−0.0042 (5)	0.0053 (5)

Geometric parameters (Å, º)

Br1—C7	1.9071 (16)	C19—C20	1.4925 (19)
Br2—C25	1.9005 (15)	C19—N1	1.3616 (18)
C1—C2	1.4940 (19)	C19—N4	1.3115 (18)
C1—N1	1.3327 (19)	C20—C21	1.4917 (19)
C1—N2	1.3250 (19)	C20—N5	1.2809 (19)
C2—C3	1.485 (2)	C21—H21A	0.9800
C2—N3	1.2818 (19)	C21—H21B	0.9800
C3—H3A	0.9800	C21—H21C	0.9800
C3—H3B	0.9800	C22—C23	1.5169 (19)
C3—H3C	0.9800	C22—C30	1.5775 (19)
C4—C5	1.514 (2)	C22—N4	1.4513 (17)
C4—C12	1.5697 (19)	C22—N5	1.4816 (17)
C4—N2	1.4471 (18)	C23—C24	1.383 (2)
C4—N3	1.4770 (17)	C23—C28	1.392 (2)
C5—C6	1.379 (2)	C24—H24	0.9500
C5—C10	1.390 (2)	C24—C25	1.389 (2)
C6—H6	0.9500	C25—C26	1.386 (2)
C6—C7	1.387 (2)	C26—H26	0.9500
C7—C8	1.389 (2)	C26—C27	1.387 (2)
C8—H8	0.9500	C27—H27	0.9500
C8—C9	1.393 (2)	C27—C28	1.390 (2)
C9—H9	0.9500	C28—C29	1.504 (2)
C9—C10	1.392 (2)	C29—H29A	0.9900
C10—C11	1.512 (2)	C29—H29B	0.9900
C11—H11A	0.9900	C29—C30	1.5489 (19)
C11—H11B	0.9900	C30—C31	1.5271 (19)
C11—C12	1.556 (2)	C30—C35	1.5441 (19)
C12—C13	1.530 (2)	C31—H31A	0.9900
C12—C17	1.545 (2)	C31—H31B	0.9900
C13—H13A	0.9900	C31—C32	1.534 (2)
C13—H13B	0.9900	C32—H32A	0.9900
C13—C14	1.528 (2)	C32—H32B	0.9900
C14—H14A	0.9900	C32—C33	1.527 (2)
C14—H14B	0.9900	C33—H33	1.0000
C14—C15	1.516 (2)	C33—C34	1.519 (2)
C15—H15	1.0000	C33—O2	1.4284 (19)
C15—C16	1.522 (2)	C34—H34A	0.9900
C15—O1	1.4311 (19)	C34—H34B	0.9900
C16—H16A	0.9900	C34—C35	1.531 (2)
C16—H16B	0.9900	C35—H35A	0.9900
C16—C17	1.529 (2)	C35—H35B	0.9900
C17—H17A	0.9900	C36—H36A	0.9800
C17—H17B	0.9900	C36—H36B	0.9800
C18—H18A	0.9800	C36—H36C	0.9800
C18—H18B	0.9800	C36—O2	1.412 (2)
C18—H18C	0.9800	N2—H2	0.823 (14)
C18—O1	1.421 (2)
N1—C1—C2	125.17 (13)	N5—C20—C21	125.43 (13)
N2—C1—C2	105.82 (12)	C20—C21—H21A	109.5
N2—C1—N1	128.98 (13)	C20—C21—H21B	109.5
C3—C2—C1	123.12 (13)	C20—C21—H21C	109.5
N3—C2—C1	111.32 (12)	H21A—C21—H21B	109.5
N3—C2—C3	125.56 (13)	H21A—C21—H21C	109.5
C2—C3—H3A	109.5	H21B—C21—H21C	109.5
C2—C3—H3B	109.5	C23—C22—C30	102.04 (11)
C2—C3—H3C	109.5	N4—C22—C23	114.04 (12)
H3A—C3—H3B	109.5	N4—C22—C30	112.98 (11)
H3A—C3—H3C	109.5	N4—C22—N5	106.87 (11)
H3B—C3—H3C	109.5	N5—C22—C23	109.73 (11)
C5—C4—C12	102.45 (11)	N5—C22—C30	111.22 (11)
N2—C4—C5	114.25 (12)	C24—C23—C22	128.04 (13)
N2—C4—C12	114.48 (12)	C24—C23—C28	122.24 (13)
N2—C4—N3	105.19 (11)	C28—C23—C22	109.71 (12)
N3—C4—C5	109.74 (11)	C23—C24—H24	121.6
N3—C4—C12	110.81 (11)	C23—C24—C25	116.76 (14)
C6—C5—C4	127.50 (13)	C25—C24—H24	121.6
C6—C5—C10	122.50 (14)	C24—C25—Br2	118.99 (12)
C10—C5—C4	109.99 (13)	C26—C25—Br2	118.59 (12)
C5—C6—H6	121.3	C26—C25—C24	122.42 (14)
C5—C6—C7	117.34 (14)	C25—C26—H26	120.2
C7—C6—H6	121.3	C25—C26—C27	119.68 (14)
C6—C7—Br1	118.08 (12)	C27—C26—H26	120.2
C6—C7—C8	121.94 (15)	C26—C27—H27	120.4
C8—C7—Br1	119.97 (12)	C26—C27—C28	119.21 (14)
C7—C8—H8	120.3	C28—C27—H27	120.4
C7—C8—C9	119.48 (14)	C23—C28—C29	110.20 (12)
C9—C8—H8	120.3	C27—C28—C23	119.68 (14)
C8—C9—H9	120.2	C27—C28—C29	130.11 (13)
C10—C9—C8	119.57 (14)	C28—C29—H29A	111.1
C10—C9—H9	120.2	C28—C29—H29B	111.1
C5—C10—C9	119.10 (14)	C28—C29—C30	103.23 (11)
C5—C10—C11	109.99 (13)	H29A—C29—H29B	109.1
C9—C10—C11	130.91 (14)	C30—C29—H29A	111.1
C10—C11—H11A	111.0	C30—C29—H29B	111.1
C10—C11—H11B	111.0	C29—C30—C22	101.61 (11)
C10—C11—C12	103.59 (11)	C31—C30—C22	112.81 (11)
H11A—C11—H11B	109.0	C31—C30—C29	113.80 (12)
C12—C11—H11A	111.0	C31—C30—C35	109.08 (12)
C12—C11—H11B	111.0	C35—C30—C22	109.10 (11)
C11—C12—C4	101.86 (11)	C35—C30—C29	110.20 (11)
C13—C12—C4	110.97 (12)	C30—C31—H31A	109.3
C13—C12—C11	114.79 (12)	C30—C31—H31B	109.3
C13—C12—C17	109.50 (12)	C30—C31—C32	111.72 (12)
C17—C12—C4	109.15 (11)	H31A—C31—H31B	107.9
C17—C12—C11	110.28 (12)	C32—C31—H31A	109.3
C12—C13—H13A	108.9	C32—C31—H31B	109.3
C12—C13—H13B	108.9	C31—C32—H32A	109.3
H13A—C13—H13B	107.7	C31—C32—H32B	109.3
C14—C13—C12	113.34 (12)	H32A—C32—H32B	108.0
C14—C13—H13A	108.9	C33—C32—C31	111.61 (13)
C14—C13—H13B	108.9	C33—C32—H32A	109.3
C13—C14—H14A	109.3	C33—C32—H32B	109.3
C13—C14—H14B	109.3	C32—C33—H33	109.0
H14A—C14—H14B	107.9	C34—C33—C32	111.30 (12)
C15—C14—C13	111.74 (13)	C34—C33—H33	109.0
C15—C14—H14A	109.3	O2—C33—C32	112.32 (13)
C15—C14—H14B	109.3	O2—C33—H33	109.0
C14—C15—H15	109.0	O2—C33—C34	106.11 (13)
C14—C15—C16	109.82 (13)	C33—C34—H34A	109.5
C16—C15—H15	109.0	C33—C34—H34B	109.5
O1—C15—C14	106.87 (13)	C33—C34—C35	110.78 (13)
O1—C15—H15	109.0	H34A—C34—H34B	108.1
O1—C15—C16	113.19 (13)	C35—C34—H34A	109.5
C15—C16—H16A	109.7	C35—C34—H34B	109.5
C15—C16—H16B	109.7	C30—C35—H35A	109.1
C15—C16—C17	109.84 (12)	C30—C35—H35B	109.1
H16A—C16—H16B	108.2	C34—C35—C30	112.68 (12)
C17—C16—H16A	109.7	C34—C35—H35A	109.1
C17—C16—H16B	109.7	C34—C35—H35B	109.1
C12—C17—H17A	109.0	H35A—C35—H35B	107.8
C12—C17—H17B	109.0	H36A—C36—H36B	109.5
C16—C17—C12	112.81 (12)	H36A—C36—H36C	109.5
C16—C17—H17A	109.0	H36B—C36—H36C	109.5
C16—C17—H17B	109.0	O2—C36—H36A	109.5
H17A—C17—H17B	107.8	O2—C36—H36B	109.5
H18A—C18—H18B	109.5	O2—C36—H36C	109.5
H18A—C18—H18C	109.5	C1—N1—C19	114.92 (12)
H18B—C18—H18C	109.5	C1—N2—C4	110.02 (12)
O1—C18—H18A	109.5	C1—N2—H2	119.8 (12)
O1—C18—H18B	109.5	C4—N2—H2	130.1 (12)
O1—C18—H18C	109.5	C2—N3—C4	107.61 (11)
N1—C19—C20	123.54 (12)	C19—N4—C22	107.66 (11)
N4—C19—C20	108.12 (12)	C20—N5—C22	106.51 (11)
N4—C19—N1	128.29 (13)	C18—O1—C15	113.31 (14)
C21—C20—C19	123.79 (12)	C36—O2—C33	113.60 (15)
N5—C20—C19	110.78 (12)
Br1—C7—C8—C9	178.42 (11)	C24—C23—C28—C29	178.36 (13)
Br2—C25—C26—C27	179.54 (12)	C24—C25—C26—C27	−0.7 (2)
C1—C2—N3—C4	1.52 (16)	C25—C26—C27—C28	0.2 (2)
C2—C1—N1—C19	−174.58 (13)	C26—C27—C28—C23	0.4 (2)
C2—C1—N2—C4	1.35 (16)	C26—C27—C28—C29	−178.16 (15)
C3—C2—N3—C4	−177.80 (14)	C27—C28—C29—C30	157.17 (15)
C4—C5—C6—C7	−177.07 (13)	C28—C23—C24—C25	−0.1 (2)
C4—C5—C10—C9	176.23 (13)	C28—C29—C30—C22	33.89 (13)
C4—C5—C10—C11	−3.85 (16)	C28—C29—C30—C31	155.44 (12)
C4—C12—C13—C14	−171.17 (13)	C28—C29—C30—C35	−81.68 (14)
C4—C12—C17—C16	174.63 (12)	C29—C30—C31—C32	68.08 (16)
C5—C4—C12—C11	−33.48 (13)	C29—C30—C35—C34	−69.81 (15)
C5—C4—C12—C13	−156.11 (12)	C30—C22—C23—C24	−156.70 (14)
C5—C4—C12—C17	83.12 (13)	C30—C22—C23—C28	22.73 (14)
C5—C4—N2—C1	119.89 (13)	C30—C22—N4—C19	−120.81 (13)
C5—C4—N3—C2	−124.03 (13)	C30—C22—N5—C20	123.30 (12)
C5—C6—C7—Br1	−179.74 (10)	C30—C31—C32—C33	56.31 (17)
C5—C6—C7—C8	0.6 (2)	C31—C30—C35—C34	55.79 (16)
C5—C10—C11—C12	−18.25 (16)	C31—C32—C33—C34	−55.19 (17)
C6—C5—C10—C9	−2.8 (2)	C31—C32—C33—O2	−174.01 (12)
C6—C5—C10—C11	177.14 (13)	C32—C33—C34—C35	54.55 (17)
C6—C7—C8—C9	−2.0 (2)	C32—C33—O2—C36	−74.54 (18)
C7—C8—C9—C10	0.9 (2)	C33—C34—C35—C30	−55.86 (16)
C8—C9—C10—C5	1.4 (2)	C34—C33—O2—C36	163.64 (15)
C8—C9—C10—C11	−178.53 (15)	C35—C30—C31—C32	−55.40 (16)
C9—C10—C11—C12	161.66 (15)	N1—C1—C2—C3	−4.1 (2)
C10—C5—C6—C7	1.8 (2)	N1—C1—C2—N3	176.53 (14)
C10—C11—C12—C4	31.57 (14)	N1—C1—N2—C4	−176.97 (14)
C10—C11—C12—C13	151.55 (12)	N1—C19—C20—C21	4.0 (2)
C10—C11—C12—C17	−84.21 (14)	N1—C19—C20—N5	−175.33 (13)
C11—C12—C13—C14	74.04 (17)	N1—C19—N4—C22	175.04 (14)
C11—C12—C17—C16	−74.26 (15)	N2—C1—C2—C3	177.46 (14)
C12—C4—C5—C6	−157.02 (14)	N2—C1—C2—N3	−1.88 (17)
C12—C4—C5—C10	24.03 (15)	N2—C1—N1—C19	3.4 (2)
C12—C4—N2—C1	−122.41 (13)	N2—C4—C5—C6	−32.6 (2)
C12—C4—N3—C2	123.55 (13)	N2—C4—C5—C10	148.42 (12)
C12—C13—C14—C15	54.37 (18)	N2—C4—C12—C11	−157.73 (12)
C13—C12—C17—C16	52.97 (16)	N2—C4—C12—C13	79.64 (15)
C13—C14—C15—C16	−57.49 (18)	N2—C4—C12—C17	−41.12 (16)
C13—C14—C15—O1	179.37 (13)	N2—C4—N3—C2	−0.68 (15)
C14—C15—C16—C17	59.04 (17)	N3—C4—C5—C6	85.21 (17)
C14—C15—O1—C18	−176.19 (14)	N3—C4—C5—C10	−93.74 (14)
C15—C16—C17—C12	−58.08 (17)	N3—C4—C12—C11	83.52 (13)
C16—C15—O1—C18	62.79 (19)	N3—C4—C12—C13	−39.11 (16)
C17—C12—C13—C14	−50.61 (17)	N3—C4—C12—C17	−159.88 (11)
C19—C20—N5—C22	−0.97 (15)	N3—C4—N2—C1	−0.52 (15)
C20—C19—N1—C1	171.64 (13)	N4—C19—C20—C21	−178.47 (13)
C20—C19—N4—C22	−2.37 (15)	N4—C19—C20—N5	2.22 (17)
C21—C20—N5—C22	179.73 (13)	N4—C19—N1—C1	−5.4 (2)
C22—C23—C24—C25	179.31 (13)	N4—C22—C23—C24	−34.6 (2)
C22—C23—C28—C27	−179.95 (13)	N4—C22—C23—C28	144.88 (12)
C22—C23—C28—C29	−1.11 (16)	N4—C22—C30—C29	−157.12 (11)
C22—C30—C31—C32	−176.82 (11)	N4—C22—C30—C31	80.65 (15)
C22—C30—C35—C34	179.43 (12)	N4—C22—C30—C35	−40.75 (15)
C23—C22—C30—C29	−34.24 (13)	N4—C22—N5—C20	−0.44 (15)
C23—C22—C30—C31	−156.47 (11)	N5—C22—C23—C24	85.28 (17)
C23—C22—C30—C35	82.13 (13)	N5—C22—C23—C28	−95.29 (14)
C23—C22—N4—C19	123.27 (13)	N5—C22—C30—C29	82.70 (13)
C23—C22—N5—C20	−124.56 (13)	N5—C22—C30—C31	−39.53 (15)
C23—C24—C25—Br2	−179.61 (10)	N5—C22—C30—C35	−160.93 (11)
C23—C24—C25—C26	0.7 (2)	N5—C22—N4—C19	1.84 (15)
C23—C28—C29—C30	−21.51 (15)	O1—C15—C16—C17	178.38 (13)
C24—C23—C28—C27	−0.5 (2)	O2—C33—C34—C35	177.03 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N4	0.82 (1)	1.95 (2)	2.5549 (16)	129 (2)