Intra­molecular π–π stacking and bromine inter­actions in (2,2′-bipyridine-κ²N,N′)dibromo-cis-bis­[1,1-diphenyl­hydrazido­(2−)]molybdenum(VI)

Mol­ecules of the title compound, [Mo(C₁₂H₁₀N₂)₂Br₂(C₁₀H₈N₂)], are linked via several weak C—H...Br inter­actions. The crystal structure shows similar unit cell parameters and packing scheme to two analogous previously reported structures. All three structures exhibit an intra­molecular aromatic π–π inter­action.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.042
• wR factor = 0.100
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.03
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.75 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Mo1    -   Br1     ..       6.08 su
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2     ..  BR2     ..       2.95 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H33    ..  BR2     ..       3.06 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H19    ..  BR1     ..       3.03 Ang.

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

   0 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
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1994); software used to prepare material for publication: PLATON (Spek, 2003) and Mercury (Macrae et al., 2006).

(2,2'-bipyridine-κ²N,N')dibromo-cis-bis[1,1- diphenylhydrazido(2-)]molybdenum(VI)

Crystal data

[Mo(C12H10N2)2Br2(C10H8N2)]	Z = 2
Mr = 776.36	F(000) = 772
Triclinic, P1	Dx = 1.613 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7449 (11) Å	Cell parameters from 999 reflections
b = 10.6706 (12) Å	θ = 2.2–26.4°
c = 17.883 (2) Å	µ = 2.94 mm^−1
α = 96.731 (2)°	T = 298 K
β = 98.989 (2)°	Polyhedron, red
γ = 117.028 (2)°	0.38 × 0.28 × 0.12 mm
V = 1598.2 (3) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	4921 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.026
Absorption correction: multi-scan [SADABS (Sheldrick, 1996) in SAINT (Bruker, 2000)]	θmax = 26.4°, θmin = 2.2°
Tmin = 0.383, Tmax = 0.702	h = −12→12
12970 measured reflections	k = −13→13
6449 independent reflections	l = −22→22

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.100	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0517P)^2] where P = (Fo^2 + 2Fc^2)/3
6449 reflections	(Δ/σ)max = 0.001
388 parameters	Δρmax = 0.63 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
Mo1	0.06731 (4)	0.03946 (3)	0.22582 (2)	0.0380 (1)
Br1	0.34224 (5)	0.22853 (5)	0.31331 (2)	0.0561 (2)
Br2	−0.17049 (5)	−0.17927 (4)	0.12868 (3)	0.0584 (2)
N1	0.1981 (3)	−0.0127 (3)	0.14091 (17)	0.0426 (10)
N2	0.1599 (4)	−0.1094 (3)	0.26951 (19)	0.0480 (11)
N3	−0.0411 (3)	0.0208 (3)	0.29760 (18)	0.0456 (10)
N4	−0.1274 (4)	0.0224 (3)	0.34753 (19)	0.0510 (11)
N5	0.0569 (3)	0.1743 (3)	0.18040 (18)	0.0408 (10)
N6	0.0403 (3)	0.2802 (3)	0.15762 (18)	0.0430 (10)
C1	0.2037 (5)	0.0295 (4)	0.0740 (2)	0.0518 (16)
C2	0.2651 (5)	−0.0130 (5)	0.0185 (3)	0.0620 (17)
C3	0.3225 (5)	−0.1063 (5)	0.0327 (3)	0.0677 (17)
C4	0.3212 (5)	−0.1489 (4)	0.1017 (3)	0.0590 (17)
C5	0.2576 (4)	−0.1018 (4)	0.1549 (2)	0.0450 (12)
C6	0.2501 (4)	−0.1434 (4)	0.2303 (2)	0.0463 (14)
C7	0.3293 (5)	−0.2114 (5)	0.2606 (3)	0.0668 (17)
C8	0.3179 (6)	−0.2440 (5)	0.3326 (3)	0.081 (2)
C9	0.2268 (6)	−0.2097 (5)	0.3717 (3)	0.0746 (19)
C10	0.1493 (5)	−0.1429 (4)	0.3387 (3)	0.0611 (17)
C11	−0.2055 (4)	−0.1033 (4)	0.3774 (2)	0.0493 (14)
C12	−0.2706 (5)	−0.2367 (5)	0.3304 (3)	0.0648 (17)
C13	−0.3435 (6)	−0.3573 (5)	0.3597 (3)	0.081 (2)
C14	−0.3521 (7)	−0.3459 (7)	0.4351 (4)	0.093 (3)
C15	−0.2859 (7)	−0.2142 (7)	0.4818 (3)	0.095 (3)
C16	−0.2116 (6)	−0.0917 (5)	0.4541 (3)	0.0692 (17)
C17	−0.1365 (5)	0.1511 (4)	0.3705 (2)	0.0502 (14)
C18	−0.2720 (6)	0.1432 (6)	0.3885 (3)	0.0718 (19)
C19	−0.2776 (8)	0.2691 (8)	0.4106 (3)	0.090 (3)
C20	−0.1520 (10)	0.3969 (8)	0.4121 (3)	0.107 (3)
C21	−0.0200 (8)	0.4040 (6)	0.3940 (3)	0.095 (3)
C22	−0.0103 (6)	0.2806 (5)	0.3731 (3)	0.0671 (17)
C23	−0.0850 (4)	0.3048 (4)	0.1729 (2)	0.0389 (11)
C24	−0.2207 (4)	0.1941 (4)	0.1835 (2)	0.0456 (12)
C25	−0.3409 (5)	0.2204 (5)	0.1989 (2)	0.0578 (16)
C26	−0.3266 (6)	0.3550 (5)	0.2030 (3)	0.0674 (19)
C27	−0.1914 (6)	0.4645 (5)	0.1927 (3)	0.0643 (17)
C28	−0.0698 (5)	0.4412 (4)	0.1786 (2)	0.0507 (14)
C29	0.1549 (4)	0.3702 (4)	0.1195 (2)	0.0403 (11)
C30	0.1079 (5)	0.3982 (4)	0.0498 (2)	0.0574 (14)
C31	0.2205 (6)	0.4853 (5)	0.0146 (3)	0.0645 (19)
C32	0.3766 (6)	0.5440 (4)	0.0479 (3)	0.0651 (19)
C33	0.4233 (5)	0.5155 (5)	0.1167 (3)	0.078 (2)
C34	0.3124 (5)	0.4294 (5)	0.1532 (3)	0.0620 (16)
H1	0.16350	0.09160	0.06420	0.0620*
H2	0.26800	0.02010	−0.02740	0.0740*
H3	0.36180	−0.14010	−0.00430	0.0820*
H4	0.36290	−0.20950	0.11270	0.0700*
H7	0.39020	−0.23530	0.23280	0.0800*
H8	0.37200	−0.28890	0.35400	0.0970*
H9	0.21720	−0.23120	0.42020	0.0900*
H10	0.08670	−0.11990	0.36560	0.0730*
H12	−0.26530	−0.24560	0.27870	0.0780*
H13	−0.38770	−0.44800	0.32760	0.0980*
H14	−0.40320	−0.42820	0.45440	0.1110*
H15	−0.29070	−0.20640	0.53360	0.1130*
H16	−0.16570	−0.00150	0.48690	0.0830*
H18	−0.35880	0.05430	0.38580	0.0860*
H19	−0.36720	0.26570	0.42430	0.1090*
H20	−0.15680	0.48140	0.42580	0.1280*
H21	0.06540	0.49320	0.39560	0.1140*
H22	0.08120	0.28580	0.36090	0.0810*
H24	−0.23140	0.10240	0.18040	0.0550*
H25	−0.43250	0.14610	0.20660	0.0700*
H26	−0.40860	0.37160	0.21260	0.0810*
H27	−0.18180	0.55580	0.19530	0.0780*
H28	0.02290	0.51700	0.17290	0.0610*
H30	0.00070	0.35850	0.02650	0.0690*
H31	0.18880	0.50390	−0.03280	0.0770*
H32	0.45180	0.60380	0.02390	0.0780*
H33	0.53080	0.55440	0.13920	0.0930*
H34	0.34490	0.41170	0.20070	0.0740*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mo1	0.0425 (2)	0.0354 (2)	0.0443 (2)	0.0212 (1)	0.0191 (2)	0.0155 (1)
Br1	0.0498 (2)	0.0577 (3)	0.0530 (3)	0.0184 (2)	0.0120 (2)	0.0165 (2)
Br2	0.0582 (3)	0.0458 (2)	0.0586 (3)	0.0148 (2)	0.0128 (2)	0.0114 (2)
N1	0.0435 (17)	0.0433 (17)	0.0466 (19)	0.0229 (15)	0.0164 (15)	0.0131 (15)
N2	0.056 (2)	0.0448 (18)	0.053 (2)	0.0285 (16)	0.0183 (16)	0.0205 (16)
N3	0.0449 (18)	0.0424 (17)	0.0468 (19)	0.0175 (15)	0.0158 (15)	0.0089 (15)
N4	0.062 (2)	0.0464 (19)	0.050 (2)	0.0260 (17)	0.0274 (17)	0.0111 (16)
N5	0.0349 (16)	0.0371 (16)	0.053 (2)	0.0177 (14)	0.0133 (14)	0.0136 (14)
N6	0.0416 (17)	0.0425 (17)	0.058 (2)	0.0252 (15)	0.0205 (15)	0.0245 (15)
C1	0.059 (3)	0.054 (2)	0.051 (3)	0.031 (2)	0.019 (2)	0.018 (2)
C2	0.067 (3)	0.074 (3)	0.050 (3)	0.033 (3)	0.028 (2)	0.016 (2)
C3	0.067 (3)	0.070 (3)	0.066 (3)	0.032 (3)	0.030 (2)	0.000 (3)
C4	0.062 (3)	0.055 (3)	0.068 (3)	0.036 (2)	0.018 (2)	0.005 (2)
C5	0.041 (2)	0.039 (2)	0.053 (2)	0.0196 (17)	0.0090 (18)	0.0043 (18)
C6	0.047 (2)	0.038 (2)	0.056 (3)	0.0224 (18)	0.0106 (19)	0.0118 (18)
C7	0.072 (3)	0.063 (3)	0.082 (3)	0.046 (3)	0.016 (3)	0.020 (3)
C8	0.092 (4)	0.077 (3)	0.093 (4)	0.056 (3)	0.011 (3)	0.036 (3)
C9	0.091 (4)	0.066 (3)	0.073 (3)	0.040 (3)	0.015 (3)	0.034 (3)
C10	0.077 (3)	0.060 (3)	0.060 (3)	0.038 (2)	0.024 (2)	0.030 (2)
C11	0.049 (2)	0.051 (2)	0.053 (3)	0.023 (2)	0.024 (2)	0.018 (2)
C12	0.079 (3)	0.055 (3)	0.067 (3)	0.030 (2)	0.036 (3)	0.022 (2)
C13	0.095 (4)	0.050 (3)	0.105 (4)	0.028 (3)	0.053 (3)	0.032 (3)
C14	0.111 (5)	0.088 (4)	0.112 (5)	0.053 (4)	0.064 (4)	0.063 (4)
C15	0.117 (5)	0.127 (5)	0.069 (4)	0.066 (4)	0.049 (4)	0.058 (4)
C16	0.081 (3)	0.078 (3)	0.054 (3)	0.037 (3)	0.030 (3)	0.020 (3)
C17	0.061 (3)	0.057 (2)	0.040 (2)	0.035 (2)	0.0128 (19)	0.0078 (19)
C18	0.071 (3)	0.092 (4)	0.060 (3)	0.051 (3)	0.009 (2)	0.002 (3)
C19	0.105 (5)	0.137 (5)	0.065 (3)	0.096 (5)	0.008 (3)	0.004 (4)
C20	0.176 (7)	0.112 (5)	0.072 (4)	0.112 (6)	0.006 (4)	0.006 (4)
C21	0.138 (6)	0.062 (3)	0.084 (4)	0.053 (4)	0.018 (4)	0.004 (3)
C22	0.087 (3)	0.053 (3)	0.061 (3)	0.033 (3)	0.022 (3)	0.008 (2)
C23	0.0377 (19)	0.046 (2)	0.039 (2)	0.0234 (17)	0.0104 (16)	0.0144 (17)
C24	0.038 (2)	0.045 (2)	0.054 (2)	0.0193 (18)	0.0114 (18)	0.0136 (18)
C25	0.044 (2)	0.076 (3)	0.059 (3)	0.029 (2)	0.021 (2)	0.022 (2)
C26	0.069 (3)	0.093 (4)	0.075 (3)	0.060 (3)	0.033 (3)	0.031 (3)
C27	0.082 (3)	0.070 (3)	0.076 (3)	0.057 (3)	0.035 (3)	0.032 (3)
C28	0.057 (2)	0.046 (2)	0.061 (3)	0.029 (2)	0.024 (2)	0.023 (2)
C29	0.041 (2)	0.0383 (19)	0.050 (2)	0.0225 (17)	0.0185 (18)	0.0147 (17)
C30	0.053 (2)	0.055 (2)	0.058 (3)	0.021 (2)	0.011 (2)	0.015 (2)
C31	0.087 (4)	0.064 (3)	0.053 (3)	0.038 (3)	0.031 (3)	0.024 (2)
C32	0.075 (3)	0.054 (3)	0.098 (4)	0.040 (3)	0.060 (3)	0.038 (3)
C33	0.048 (3)	0.081 (3)	0.124 (5)	0.033 (3)	0.039 (3)	0.059 (3)
C34	0.046 (2)	0.067 (3)	0.083 (3)	0.029 (2)	0.018 (2)	0.041 (3)

Geometric parameters (Å, º)

Mo1—Br1	2.5950 (7)	C24—C25	1.381 (7)
Mo1—Br2	2.5906 (6)	C25—C26	1.370 (7)
Mo1—N1	2.300 (3)	C26—C27	1.365 (8)
Mo1—N2	2.307 (4)	C27—C28	1.370 (8)
Mo1—N3	1.760 (3)	C29—C30	1.373 (5)
Mo1—N5	1.767 (3)	C29—C34	1.363 (7)
N1—C1	1.327 (5)	C30—C31	1.375 (7)
N1—C5	1.347 (5)	C31—C32	1.351 (8)
N2—C6	1.349 (6)	C32—C33	1.361 (7)
N2—C10	1.334 (6)	C33—C34	1.377 (7)
N3—N4	1.323 (5)	C1—H1	0.9300
N4—C11	1.425 (5)	C2—H2	0.9300
N4—C17	1.433 (5)	C3—H3	0.9300
N5—N6	1.312 (4)	C4—H4	0.9300
N6—C23	1.419 (5)	C7—H7	0.9300
N6—C29	1.432 (5)	C8—H8	0.9300
C1—C2	1.370 (7)	C9—H9	0.9300
C2—C3	1.375 (7)	C10—H10	0.9300
C3—C4	1.364 (7)	C12—H12	0.9300
C4—C5	1.377 (7)	C13—H13	0.9300
C5—C6	1.470 (5)	C14—H14	0.9300
C6—C7	1.373 (7)	C15—H15	0.9300
C7—C8	1.381 (7)	C16—H16	0.9300
C8—C9	1.357 (9)	C18—H18	0.9300
C9—C10	1.369 (8)	C19—H19	0.9300
C11—C12	1.367 (6)	C20—H20	0.9300
C11—C16	1.376 (6)	C21—H21	0.9300
C12—C13	1.371 (7)	C22—H22	0.9300
C13—C14	1.359 (9)	C24—H24	0.9300
C14—C15	1.350 (9)	C25—H25	0.9300
C15—C16	1.372 (8)	C26—H26	0.9300
C17—C18	1.376 (8)	C27—H27	0.9300
C17—C22	1.359 (7)	C28—H28	0.9300
C18—C19	1.383 (10)	C30—H30	0.9300
C19—C20	1.350 (11)	C31—H31	0.9300
C20—C21	1.346 (13)	C32—H32	0.9300
C21—C22	1.375 (9)	C33—H33	0.9300
C23—C24	1.375 (6)	C34—H34	0.9300
C23—C28	1.384 (6)
Mo1···C22	3.864 (6)	C4···H25^i	3.0900
Mo1···C24	3.874 (4)	C4···H7	2.7200
Mo1···H12	3.6500	C5···H25^i	2.8800
Mo1···H22	3.2900	C7···H28^v	3.0600
Mo1···H24	3.2800	C7···H4	2.7200
Br1···N1	3.407 (3)	C9···H21^v	2.9500
Br1···N2	3.139 (3)	C11···H18	2.7200
Br1···N3	3.309 (3)	C11···H10	2.9700
Br1···N5	3.141 (3)	C12···H10	3.0400
Br1···C6	3.705 (4)	C16···H18	2.8100
Br1···C10	3.656 (4)	C17···H16	2.7600
Br1···C19^i	3.646 (8)	C18···H16	2.8400
Br2···N2	3.480 (4)	C23···H30	2.9100
Br2···N3	3.182 (3)	C27···H31^x	2.9200
Br2···N5	3.308 (3)	C28···H31^x	2.9200
Br2···C1	3.668 (5)	C28···H30	3.0400
Br2···C31^ii	3.697 (5)	C29···H28	2.6200
Br2···N1	3.158 (3)	C29···H1	3.0600
Br1···H15^iii	2.8800	C30···H28	2.8300
Br1···H34	2.9600	C31···H4^xi	3.0700
Br1···H19^i	3.0300	C32···H4^xi	2.8200
Br1···H22	3.0900	C32···H32^ix	3.0900
Br1···H26^i	3.1800	H1···N5	2.6900
Br1···H13^iv	3.2000	H1···C29	3.0600
Br2···H27^v	3.1600	H2···Br2^ii	2.9500
Br2···H33^vi	3.0600	H4···C7	2.7200
Br2···H12	3.0300	H4···C31^v	3.0700
Br2···H2^ii	2.9500	H4···C32^v	2.8200
N1···Br1	3.407 (3)	H4···H7	2.1900
N1···Br2	3.158 (3)	H7···C4	2.7200
N1···N2	2.640 (4)	H7···H4	2.1900
N1···N5	2.974 (5)	H9···H21^v	2.5600
N1···C6	2.381 (5)	H10···N3	2.6300
N2···Br1	3.139 (3)	H10···C11	2.9700
N2···Br2	3.480 (4)	H10···C12	3.0400
N2···N1	2.640 (4)	H12···Mo1	3.6500
N2···N3	2.939 (5)	H12···Br2	3.0300
N2···C5	2.386 (5)	H12···N3	2.6200
N3···Br1	3.309 (3)	H13···Br1^vi	3.2000
N3···Br2	3.182 (3)	H13···H26^v	2.5600
N3···N2	2.939 (5)	H15···Br1^iii	2.8800
N3···N5	2.828 (4)	H16···C17	2.7600
N3···C10	3.139 (6)	H16···C18	2.8400
N5···C1	3.198 (6)	H18···C11	2.7200
N5···Br2	3.308 (3)	H18···C16	2.8100
N5···N1	2.974 (5)	H19···Br1^vii	3.0300
N5···Br1	3.141 (3)	H21···C9^xi	2.9500
N5···N3	2.828 (4)	H21···H9^xi	2.5600
N3···H12	2.6200	H22···Mo1	3.2900
N3···H22	2.5400	H22···Br1	3.0900
N3···H10	2.6300	H22···N3	2.5400
N5···H1	2.6900	H24···Mo1	3.2800
N5···H24	2.5500	H24···N5	2.5500
N5···H34	2.7300	H25···C4^vii	3.0900
C16···C18	3.134 (8)	H25···C5^vii	2.8800
C17···C24	3.451 (5)	H26···Br1^vii	3.1800
C18···C16	3.134 (8)	H26···H13^xi	2.5600
C19···Br1^vii	3.646 (8)	H27···Br2^xi	3.1600
C20···C21^viii	3.545 (8)	H28···C7^xi	3.0600
C21···C20^viii	3.545 (8)	H28···C29	2.6200
C22···C24	3.453 (6)	H28···C30	2.8300
C22···Mo1	3.864 (6)	H30···C23	2.9100
C24···C17	3.451 (5)	H30···C28	3.0400
C24···C22	3.453 (6)	H30···C3^ii	2.9800
C24···Mo1	3.874 (4)	H31···C27^x	2.9200
C28···C30	3.199 (6)	H31···C28^x	2.9200
C30···C28	3.199 (6)	H32···C32^ix	3.0900
C31···Br2^ii	3.697 (5)	H33···Br2^iv	3.0600
C32···C32^ix	3.545 (8)	H34···Br1	2.9600
C3···H30^ii	2.9800	H34···N5	2.7300
Br1—Mo1—Br2	166.50 (2)	C23—C28—C27	119.9 (4)
Br1—Mo1—N1	87.98 (8)	N6—C29—C30	120.8 (4)
Br1—Mo1—N2	79.40 (8)	N6—C29—C34	119.5 (4)
Br1—Mo1—N3	97.03 (10)	C30—C29—C34	119.8 (4)
Br1—Mo1—N5	90.07 (10)	C29—C30—C31	119.5 (5)
Br2—Mo1—N1	80.18 (8)	C30—C31—C32	120.8 (5)
Br2—Mo1—N2	90.37 (8)	C31—C32—C33	119.7 (5)
Br2—Mo1—N3	91.99 (10)	C32—C33—C34	120.4 (5)
Br2—Mo1—N5	96.97 (10)	C29—C34—C33	119.8 (5)
N1—Mo1—N2	69.91 (12)	N1—C1—H1	118.00
N1—Mo1—N3	159.64 (12)	C2—C1—H1	118.00
N1—Mo1—N5	93.03 (13)	C1—C2—H2	121.00
N2—Mo1—N3	91.55 (14)	C3—C2—H2	121.00
N2—Mo1—N5	160.06 (14)	C2—C3—H3	120.00
N3—Mo1—N5	106.63 (15)	C4—C3—H3	120.00
Mo1—N1—C1	122.5 (3)	C3—C4—H4	120.00
Mo1—N1—C5	119.4 (2)	C5—C4—H4	120.00
C1—N1—C5	117.7 (3)	C6—C7—H7	120.00
Mo1—N2—C6	118.8 (2)	C8—C7—H7	120.00
Mo1—N2—C10	121.7 (3)	C7—C8—H8	120.00
C6—N2—C10	118.6 (4)	C9—C8—H8	120.00
Mo1—N3—N4	170.9 (3)	C8—C9—H9	120.00
N3—N4—C11	118.6 (3)	C10—C9—H9	121.00
N3—N4—C17	118.8 (3)	N2—C10—H10	119.00
C11—N4—C17	122.6 (4)	C9—C10—H10	119.00
Mo1—N5—N6	169.6 (3)	C11—C12—H12	120.00
N5—N6—C23	120.1 (3)	C13—C12—H12	120.00
N5—N6—C29	117.6 (3)	C12—C13—H13	120.00
C23—N6—C29	122.3 (3)	C14—C13—H13	120.00
N1—C1—C2	123.9 (4)	C13—C14—H14	120.00
C1—C2—C3	117.9 (5)	C15—C14—H14	120.00
C2—C3—C4	119.3 (5)	C14—C15—H15	119.00
C3—C4—C5	119.6 (4)	C16—C15—H15	120.00
N1—C5—C4	121.5 (4)	C11—C16—H16	120.00
N1—C5—C6	115.3 (3)	C15—C16—H16	120.00
C4—C5—C6	123.2 (4)	C17—C18—H18	120.00
N2—C6—C5	115.6 (4)	C19—C18—H18	120.00
N2—C6—C7	120.9 (4)	C18—C19—H19	120.00
C5—C6—C7	123.5 (4)	C20—C19—H19	120.00
C6—C7—C8	119.6 (5)	C19—C20—H20	119.00
C7—C8—C9	119.2 (5)	C21—C20—H20	119.00
C8—C9—C10	119.0 (5)	C20—C21—H21	120.00
N2—C10—C9	122.7 (5)	C22—C21—H21	120.00
N4—C11—C12	120.0 (4)	C17—C22—H22	121.00
N4—C11—C16	120.5 (4)	C21—C22—H22	120.00
C12—C11—C16	119.5 (4)	C23—C24—H24	120.00
C11—C12—C13	119.8 (5)	C25—C24—H24	120.00
C12—C13—C14	120.8 (5)	C24—C25—H25	120.00
C13—C14—C15	119.5 (6)	C26—C25—H25	120.00
C14—C15—C16	121.0 (5)	C25—C26—H26	120.00
C11—C16—C15	119.5 (5)	C27—C26—H26	120.00
N4—C17—C18	120.4 (4)	C26—C27—H27	120.00
N4—C17—C22	119.0 (5)	C28—C27—H27	120.00
C18—C17—C22	120.7 (5)	C23—C28—H28	120.00
C17—C18—C19	119.2 (6)	C27—C28—H28	120.00
C18—C19—C20	119.5 (8)	C29—C30—H30	120.00
C19—C20—C21	121.1 (8)	C31—C30—H30	120.00
C20—C21—C22	120.6 (6)	C30—C31—H31	120.00
C17—C22—C21	119.0 (6)	C32—C31—H31	120.00
N6—C23—C24	120.3 (4)	C31—C32—H32	120.00
N6—C23—C28	120.0 (4)	C33—C32—H32	120.00
C24—C23—C28	119.7 (4)	C32—C33—H33	120.00
C23—C24—C25	119.4 (4)	C34—C33—H33	120.00
C24—C25—C26	120.7 (5)	C29—C34—H34	120.00
C25—C26—C27	119.6 (6)	C33—C34—H34	120.00
C26—C27—C28	120.6 (5)
Br1—Mo1—N1—C1	−105.9 (3)	N1—C1—C2—C3	0.8 (7)
Br1—Mo1—N1—C5	81.3 (3)	C1—C2—C3—C4	−2.2 (7)
Br2—Mo1—N1—C1	80.7 (3)	C2—C3—C4—C5	2.2 (7)
Br2—Mo1—N1—C5	−92.2 (3)	C3—C4—C5—N1	−0.9 (7)
N2—Mo1—N1—C1	174.7 (3)	C3—C4—C5—C6	179.5 (4)
N2—Mo1—N1—C5	1.8 (3)	N1—C5—C6—C7	−167.9 (4)
N3—Mo1—N1—C1	149.3 (4)	C4—C5—C6—N2	−168.7 (4)
N3—Mo1—N1—C5	−23.6 (5)	C4—C5—C6—C7	11.8 (7)
N5—Mo1—N1—C1	−15.9 (3)	N1—C5—C6—N2	11.6 (5)
N5—Mo1—N1—C5	171.3 (3)	N2—C6—C7—C8	−0.7 (7)
Br1—Mo1—N2—C6	−86.9 (3)	C5—C6—C7—C8	178.7 (4)
Br1—Mo1—N2—C10	81.8 (3)	C6—C7—C8—C9	0.8 (8)
Br2—Mo1—N2—C6	84.2 (3)	C7—C8—C9—C10	−0.3 (8)
Br2—Mo1—N2—C10	−107.1 (3)	C8—C9—C10—N2	−0.2 (7)
N1—Mo1—N2—C6	4.8 (3)	C12—C11—C16—C15	−1.4 (9)
N1—Mo1—N2—C10	173.5 (4)	N4—C11—C16—C15	−179.3 (5)
N3—Mo1—N2—C6	176.2 (3)	N4—C11—C12—C13	179.0 (5)
N3—Mo1—N2—C10	−15.1 (3)	C16—C11—C12—C13	1.1 (8)
Mo1—N1—C1—C2	−172.5 (4)	C11—C12—C13—C14	0.1 (9)
C5—N1—C1—C2	0.5 (6)	C12—C13—C14—C15	−1.0 (11)
Mo1—N1—C5—C6	−7.6 (4)	C13—C14—C15—C16	0.7 (11)
C1—N1—C5—C6	179.2 (4)	C14—C15—C16—C11	0.5 (11)
Mo1—N1—C5—C4	172.7 (3)	N4—C17—C18—C19	179.9 (4)
C1—N1—C5—C4	−0.5 (6)	C18—C17—C22—C21	0.0 (7)
Mo1—N2—C6—C7	169.2 (3)	C22—C17—C18—C19	−1.1 (7)
C6—N2—C10—C9	0.3 (6)	N4—C17—C22—C21	179.0 (4)
Mo1—N2—C10—C9	−168.4 (4)	C17—C18—C19—C20	1.8 (8)
Mo1—N2—C6—C5	−10.3 (4)	C18—C19—C20—C21	−1.4 (9)
C10—N2—C6—C7	0.2 (6)	C19—C20—C21—C22	0.3 (9)
C10—N2—C6—C5	−179.4 (4)	C20—C21—C22—C17	0.4 (8)
C17—N4—C11—C12	143.3 (5)	C28—C23—C24—C25	0.7 (5)
N3—N4—C11—C16	140.1 (5)	N6—C23—C28—C27	179.5 (4)
N3—N4—C11—C12	−37.8 (6)	N6—C23—C24—C25	179.5 (3)
C11—N4—C17—C22	147.8 (4)	C24—C23—C28—C27	−1.7 (6)
N3—N4—C17—C22	−31.1 (6)	C23—C24—C25—C26	0.6 (6)
C17—N4—C11—C16	−38.8 (6)	C24—C25—C26—C27	−0.8 (7)
C11—N4—C17—C18	−33.1 (6)	C25—C26—C27—C28	−0.2 (8)
N3—N4—C17—C18	148.0 (4)	C26—C27—C28—C23	1.5 (7)
N5—N6—C23—C28	154.0 (3)	N6—C29—C30—C31	179.8 (4)
C23—N6—C29—C34	127.0 (4)	N6—C29—C34—C33	179.7 (4)
C29—N6—C23—C28	−24.2 (5)	C30—C29—C34—C33	−0.8 (7)
C29—N6—C23—C24	157.0 (3)	C34—C29—C30—C31	0.3 (7)
C23—N6—C29—C30	−52.5 (5)	C29—C30—C31—C32	−0.3 (7)
N5—N6—C23—C24	−24.9 (5)	C30—C31—C32—C33	0.7 (8)
N5—N6—C29—C34	−51.2 (5)	C31—C32—C33—C34	−1.2 (8)
N5—N6—C29—C30	129.3 (4)	C32—C33—C34—C29	1.2 (8)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···Br1^iii	0.93	2.88	3.799 (6)	171
C2—H2···Br2^ii	0.93	2.95	3.770 (5)	147
C33—H33···Br2^iv	0.93	3.06	3.765 (5)	134
C19—H19···Br1^vii	0.93	3.03	3.646 (8)	126

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