Crystal structures of a manganese(I) and a rhenium(I) complex of a bi­pyridine ligand with a non-coordinating benzoic acid moiety

In the title Mn^I and Re^I complexes of the ligand 2-(2,2′-bipyridin-6-yl)benzoic acid, the o-benzoic acid substituent does not coordinate to the metal. In fac-[2-(2,2′-bipyridin-6-yl)benzoic acid-κ²N,N′]tri­carbonyl­chlorido­rhenium(I) tetra­hydro­furan monosolvate, the benzoic acid fragment is positioned near the axial carbonyl ligand, whereas in fac-[2-(2,2′-bipyridin-6-yl)benzoic acid-κ²N,N′]bromido­tri­carbonyl­manganese(I) tetra­hydro­furan monosolvate, the benzoic acid fragment is disordered, such that in the major component the benzoic fragment is positioned near the bromide ligand and in the minor fragment near the axial carbonyl ligand.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.041
• wR factor = 0.104
• Data-to-parameter ratio = 20.2

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor       O4       --H4A            Please Check

Alert level C
PLAT411_ALERT_2_C Short Inter H...H Contact  H11      ..H17A             2.13 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         26 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         18 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         18 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT014_ALERT_1_G N.O.K.   _shelx_fab_checksum Found in CIF ......     Please Check
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          1 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          1 Report
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Br1      --Mn1       .       23.5 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Mn1      --C1        .        5.1 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Mn1      --C2        .        6.2 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Mn1      --C3        .       12.0 s.u.
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        31% Note
PLAT432_ALERT_2_G Short Inter X...Y Contact  C11      ..C17A             3.09 Ang.
PLAT432_ALERT_2_G Short Inter X...Y Contact  C11      ..C16A             3.12 Ang.
PLAT605_ALERT_4_G Largest Solvent Accessible VOID in the Structure        242 A   3  
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          1 Note
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        149 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         24 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...         26 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  12 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
   5 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check




Datablock: II


Alert level C
PLAT220_ALERT_2_C Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range        3.1 Ratio
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          9 Report
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  0.72A   From Re1             1.63 eA-3
PLAT972_ALERT_2_C Check Calcd Resid. Dens.  0.70A   From Re1            -1.61 eA-3

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         10 Note
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          2 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          3 Report
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Re1      --N2        .        6.2 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Re1      --C1        .        5.6 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Re1      --C2        .        6.8 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Re1      --C3        .        8.1 s.u.
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )       100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  3  )       100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  4  )       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ...... Resd  2          8.74 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ...... Resd  3          2.63 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ...... Resd  4          1.64 Check
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O6             109.5 Degree
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O6A            108.3 Degree
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O6B            109.5 Degree
PLAT432_ALERT_2_G Short Inter X...Y Contact  O1       ..C23B             2.97 Ang.
PLAT432_ALERT_2_G Short Inter X...Y Contact  O3       ..C22B             2.91 Ang.
PLAT432_ALERT_2_G Short Inter X...Y Contact  O6A      ..C4               3.02 Ang.
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         27 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          8 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          9 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  16 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
   9 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

For both structures, data collection: APEX3 (Bruker, 2015); cell refinement: SAINT-Plus (Bruker, 2015); data reduction: SAINT-Plus (Bruker, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 2009).

fac-Bromido[2-(2,2'-bipyridin-6-yl)benzoic acid-κ²N,N']tricarbonylmanganese(I) tetrahydrofuran monosolvate (I)

Crystal data

[MnBr(C17H12N2O2)(CO)3]·C4H8O	F(000) = 984
Mr = 495.17	Dx = 1.434 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.525 (3) Å	Cell parameters from 9894 reflections
b = 18.187 (5) Å	θ = 2.2–28.9°
c = 12.459 (4) Å	µ = 2.35 mm^−1
β = 105.928 (13)°	T = 100 K
V = 2293.2 (12) Å^3	Needle, yellow
Z = 4	0.21 × 0.04 × 0.03 mm

Data collection

Bruker SMART APEXIII area detector diffractometer	6992 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	5393 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.048
Detector resolution: 7.9 pixels mm^-1	θmax = 30.6°, θmin = 2.0°
0.5° ω and 0.5° φ scans	h = −15→15
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −26→25
Tmin = 0.673, Tmax = 0.802	l = −17→17
51901 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.0415P)^2 + 3.4283P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
6992 reflections	Δρmax = 0.59 e Å^−3
346 parameters	Δρmin = −0.76 e Å^−3
149 restraints

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)
Br1	0.81210 (3)	0.58497 (2)	0.67241 (2)	0.03094 (8)
Mn1	0.79215 (3)	0.67459 (2)	0.51236 (3)	0.02312 (9)
O1	0.8538 (2)	0.79491 (12)	0.6780 (2)	0.0465 (6)
O2	1.08314 (18)	0.67387 (11)	0.57136 (18)	0.0358 (4)
O3	0.7716 (2)	0.77396 (12)	0.32364 (19)	0.0422 (5)
N1	0.7657 (2)	0.58451 (10)	0.41253 (18)	0.0250 (4)
N2	0.58835 (19)	0.66090 (10)	0.47642 (18)	0.0231 (4)
C1	0.8213 (2)	0.74942 (14)	0.6135 (2)	0.0312 (6)
C2	0.9700 (2)	0.67300 (13)	0.5454 (2)	0.0276 (5)
C3	0.7791 (2)	0.73615 (14)	0.3956 (3)	0.0319 (6)
C4	0.8611 (3)	0.55066 (14)	0.3774 (2)	0.0320 (6)
H4	0.9461	0.5727	0.3938	0.038*
C5	0.8408 (3)	0.48547 (15)	0.3187 (2)	0.0365 (6)
H5	0.9105	0.4628	0.2960	0.044*
C6	0.7168 (3)	0.45389 (15)	0.2939 (3)	0.0399 (7)
H6	0.7000	0.4089	0.2538	0.048*
C7	0.6172 (3)	0.48852 (15)	0.3280 (3)	0.0361 (6)
H7	0.5313	0.4676	0.3113	0.043*
C8	0.6446 (2)	0.55402 (13)	0.3867 (2)	0.0265 (5)
C9	0.5448 (2)	0.59597 (12)	0.4244 (2)	0.0247 (5)
C10	0.4168 (3)	0.57149 (15)	0.4078 (3)	0.0352 (6)
H10	0.3897	0.5259	0.3714	0.042*
C11	0.3283 (3)	0.61409 (16)	0.4449 (3)	0.0415 (7)
H11	0.2408	0.5973	0.4370	0.050*
C12	0.3689 (3)	0.68058 (15)	0.4929 (3)	0.0365 (6)
H12	0.3088	0.7114	0.5166	0.044*
C13	0.4982 (2)	0.70278 (13)	0.5069 (2)	0.0276 (5)
O4	0.5438 (3)	0.69265 (14)	0.7265 (2)	0.0426 (7)	0.748 (3)
H4A	0.5453	0.6705	0.7860	0.064*	0.748 (3)
O5	0.5472 (3)	0.79126 (15)	0.8336 (2)	0.0375 (7)	0.748 (3)
C14	0.5363 (3)	0.78182 (19)	0.5386 (3)	0.0255 (7)	0.748 (3)
C15	0.5461 (5)	0.8292 (2)	0.4543 (4)	0.0335 (10)	0.748 (3)
H15	0.5330	0.8108	0.3807	0.040*	0.748 (3)
C16	0.5748 (5)	0.9035 (2)	0.4753 (4)	0.0411 (9)	0.748 (3)
H16	0.5847	0.9351	0.4174	0.049*	0.748 (3)
C17	0.5889 (4)	0.9309 (2)	0.5823 (4)	0.0393 (9)	0.748 (3)
H17	0.6067	0.9816	0.5975	0.047*	0.748 (3)
C18	0.5768 (4)	0.8846 (2)	0.6650 (4)	0.0300 (9)	0.748 (3)
H18	0.5873	0.9037	0.7379	0.036*	0.748 (3)
C19	0.5495 (3)	0.80940 (17)	0.6456 (3)	0.0260 (7)	0.748 (3)
C20	0.5467 (5)	0.7646 (2)	0.7440 (4)	0.0277 (8)	0.748 (3)
O4A	0.4563 (8)	0.8099 (4)	0.3602 (6)	0.0343 (19)	0.252 (3)
H4AA	0.4104	0.8358	0.3080	0.051*	0.252 (3)
O5A	0.5901 (11)	0.9062 (5)	0.3988 (8)	0.053 (3)	0.252 (3)
C14A	0.5335 (9)	0.7683 (5)	0.5909 (9)	0.024 (2)	0.252 (3)
C15A	0.5520 (14)	0.7576 (7)	0.7034 (10)	0.027 (3)	0.252 (3)
H15A	0.5446	0.7098	0.7319	0.033*	0.252 (3)
C16A	0.5818 (10)	0.8179 (5)	0.7748 (8)	0.028 (2)	0.252 (3)
H16A	0.5914	0.8127	0.8525	0.034*	0.252 (3)
C17A	0.5970 (11)	0.8861 (5)	0.7292 (9)	0.029 (2)	0.252 (3)
H17A	0.6121	0.9277	0.7772	0.035*	0.252 (3)
C18A	0.5916 (11)	0.8967 (6)	0.6210 (9)	0.024 (2)	0.252 (3)
H18A	0.6125	0.9429	0.5947	0.029*	0.252 (3)
C19A	0.5536 (8)	0.8360 (4)	0.5484 (7)	0.0224 (18)	0.252 (3)
C20A	0.5423 (17)	0.8528 (7)	0.4324 (10)	0.034 (3)	0.252 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02879 (13)	0.02479 (12)	0.04266 (16)	−0.00564 (9)	0.01555 (11)	0.00050 (10)
Mn1	0.02055 (17)	0.01701 (15)	0.0360 (2)	−0.00424 (12)	0.01480 (15)	−0.00188 (14)
O1	0.0328 (10)	0.0387 (11)	0.0734 (16)	−0.0104 (9)	0.0234 (11)	−0.0271 (11)
O2	0.0229 (9)	0.0385 (10)	0.0490 (12)	−0.0039 (7)	0.0148 (8)	0.0071 (9)
O3	0.0390 (11)	0.0416 (11)	0.0484 (13)	−0.0009 (9)	0.0160 (10)	0.0083 (10)
N1	0.0253 (10)	0.0208 (9)	0.0327 (11)	−0.0001 (7)	0.0144 (9)	0.0007 (8)
N2	0.0218 (9)	0.0171 (8)	0.0340 (11)	−0.0034 (7)	0.0139 (8)	−0.0027 (8)
C1	0.0220 (11)	0.0286 (12)	0.0481 (16)	−0.0055 (9)	0.0183 (11)	−0.0071 (11)
C2	0.0281 (12)	0.0219 (10)	0.0378 (14)	−0.0031 (9)	0.0172 (11)	0.0031 (10)
C3	0.0239 (12)	0.0224 (11)	0.0532 (17)	−0.0046 (9)	0.0173 (12)	−0.0046 (11)
C4	0.0303 (13)	0.0305 (12)	0.0402 (15)	0.0029 (10)	0.0182 (12)	0.0009 (11)
C5	0.0420 (15)	0.0334 (13)	0.0394 (15)	0.0132 (11)	0.0200 (13)	−0.0015 (11)
C6	0.0484 (17)	0.0271 (13)	0.0469 (17)	0.0033 (12)	0.0178 (14)	−0.0119 (12)
C7	0.0363 (14)	0.0267 (12)	0.0473 (17)	−0.0057 (10)	0.0151 (13)	−0.0132 (11)
C8	0.0287 (12)	0.0197 (10)	0.0347 (13)	−0.0025 (9)	0.0150 (10)	−0.0049 (9)
C9	0.0247 (11)	0.0197 (10)	0.0330 (13)	−0.0044 (8)	0.0134 (10)	−0.0038 (9)
C10	0.0296 (13)	0.0276 (12)	0.0539 (18)	−0.0117 (10)	0.0206 (13)	−0.0121 (12)
C11	0.0260 (13)	0.0384 (14)	0.068 (2)	−0.0138 (11)	0.0261 (14)	−0.0121 (14)
C12	0.0284 (13)	0.0325 (13)	0.0559 (18)	−0.0017 (10)	0.0237 (13)	−0.0102 (12)
C13	0.0257 (11)	0.0217 (10)	0.0387 (14)	−0.0012 (9)	0.0143 (10)	−0.0060 (10)
O4	0.068 (2)	0.0295 (13)	0.0364 (15)	0.0106 (12)	0.0239 (15)	0.0043 (11)
O5	0.0448 (16)	0.0388 (14)	0.0356 (15)	−0.0106 (12)	0.0223 (12)	−0.0067 (11)
C14	0.0217 (15)	0.0238 (16)	0.0346 (19)	0.0003 (12)	0.0137 (15)	−0.0061 (14)
C15	0.041 (2)	0.026 (2)	0.036 (2)	−0.0005 (17)	0.0158 (19)	−0.0044 (16)
C16	0.056 (3)	0.0269 (17)	0.043 (2)	−0.0034 (16)	0.0183 (19)	−0.0004 (15)
C17	0.055 (3)	0.0223 (17)	0.044 (2)	−0.0020 (16)	0.0189 (19)	−0.0034 (16)
C18	0.034 (2)	0.0257 (17)	0.034 (2)	0.0016 (14)	0.016 (2)	−0.0077 (17)
C19	0.0243 (15)	0.0233 (14)	0.0327 (17)	0.0036 (11)	0.0117 (13)	−0.0038 (13)
C20	0.0226 (17)	0.0299 (18)	0.034 (2)	0.0031 (13)	0.0132 (18)	0.0016 (16)
O4A	0.047 (4)	0.030 (3)	0.021 (3)	−0.016 (3)	0.002 (3)	0.004 (3)
O5A	0.076 (7)	0.043 (4)	0.038 (5)	−0.033 (4)	0.015 (4)	0.007 (4)
C14A	0.022 (4)	0.022 (4)	0.035 (5)	−0.004 (3)	0.017 (4)	0.000 (3)
C15A	0.023 (5)	0.028 (4)	0.036 (5)	−0.003 (3)	0.017 (4)	−0.007 (4)
C16A	0.033 (5)	0.024 (4)	0.031 (4)	−0.002 (3)	0.014 (4)	−0.003 (3)
C17A	0.039 (6)	0.019 (4)	0.037 (5)	0.001 (3)	0.021 (5)	−0.006 (3)
C18A	0.027 (5)	0.017 (4)	0.031 (5)	−0.003 (3)	0.014 (4)	−0.001 (3)
C19A	0.025 (4)	0.018 (3)	0.029 (4)	−0.004 (3)	0.014 (3)	0.000 (3)
C20A	0.046 (7)	0.033 (6)	0.026 (4)	−0.017 (5)	0.015 (4)	0.001 (3)

Geometric parameters (Å, º)

Br1—Mn1	2.5391 (7)	C13—C14A	1.562 (10)
Mn1—N1	2.029 (2)	O4—H4A	0.8400
Mn1—N2	2.082 (2)	O4—C20	1.326 (5)
Mn1—C1	1.822 (3)	O5—C20	1.215 (5)
Mn1—C2	1.803 (3)	C14—C15	1.384 (6)
Mn1—C3	1.810 (3)	C14—C19	1.395 (5)
O1—C1	1.139 (3)	C15—H15	0.9500
O2—C2	1.145 (3)	C15—C16	1.394 (5)
O3—C3	1.116 (3)	C16—H16	0.9500
N1—C4	1.349 (3)	C16—C17	1.392 (6)
N1—C8	1.345 (3)	C17—H17	0.9500
N2—C9	1.364 (3)	C17—C18	1.364 (6)
N2—C13	1.350 (3)	C18—H18	0.9500
C4—H4	0.9500	C18—C19	1.405 (5)
C4—C5	1.378 (4)	C19—C20	1.479 (5)
C5—H5	0.9500	O4A—H4AA	0.8400
C5—C6	1.381 (4)	O4A—C20A	1.338 (13)
C6—H6	0.9500	O5A—C20A	1.220 (12)
C6—C7	1.386 (4)	C14A—C15A	1.375 (13)
C7—H7	0.9500	C14A—C19A	1.378 (10)
C7—C8	1.386 (3)	C15A—H15A	0.9500
C8—C9	1.476 (3)	C15A—C16A	1.393 (12)
C9—C10	1.379 (3)	C16A—H16A	0.9500
C10—H10	0.9500	C16A—C17A	1.391 (12)
C10—C11	1.384 (4)	C17A—H17A	0.9500
C11—H11	0.9500	C17A—C18A	1.346 (12)
C11—C12	1.365 (4)	C18A—H18A	0.9500
C12—H12	0.9500	C18A—C19A	1.414 (11)
C12—C13	1.384 (4)	C19A—C20A	1.449 (12)
C13—C14	1.515 (4)
N1—Mn1—Br1	86.05 (6)	C13—C12—H12	120.3
N1—Mn1—N2	79.15 (8)	N2—C13—C12	122.9 (2)
N2—Mn1—Br1	87.16 (6)	N2—C13—C14	117.0 (2)
C1—Mn1—Br1	88.54 (9)	N2—C13—C14A	124.3 (4)
C1—Mn1—N1	174.43 (11)	C12—C13—C14	119.3 (2)
C1—Mn1—N2	101.88 (9)	C12—C13—C14A	110.6 (4)
C2—Mn1—Br1	87.32 (8)	C20—O4—H4A	109.5
C2—Mn1—N1	94.95 (10)	C15—C14—C13	117.5 (3)
C2—Mn1—N2	172.18 (9)	C15—C14—C19	119.5 (3)
C2—Mn1—C1	83.50 (11)	C19—C14—C13	122.7 (3)
C3—Mn1—Br1	178.20 (8)	C14—C15—H15	119.4
C3—Mn1—N1	92.27 (11)	C14—C15—C16	121.3 (4)
C3—Mn1—N2	93.14 (10)	C16—C15—H15	119.4
C3—Mn1—C1	93.13 (13)	C15—C16—H16	120.4
C3—Mn1—C2	92.21 (11)	C15—C16—C17	119.2 (4)
C4—N1—Mn1	125.32 (18)	C17—C16—H16	120.4
C8—N1—Mn1	116.16 (16)	C16—C17—H17	120.2
C8—N1—C4	118.3 (2)	C18—C17—C16	119.7 (4)
C9—N2—Mn1	113.44 (15)	C18—C17—H17	120.2
C13—N2—Mn1	129.34 (16)	C17—C18—H18	119.1
C13—N2—C9	116.8 (2)	C17—C18—C19	121.9 (4)
O1—C1—Mn1	172.5 (2)	C19—C18—H18	119.1
O2—C2—Mn1	176.5 (2)	C14—C19—C18	118.5 (4)
O3—C3—Mn1	179.7 (3)	C14—C19—C20	125.1 (3)
N1—C4—H4	118.5	C18—C19—C20	116.3 (4)
N1—C4—C5	122.9 (3)	O4—C20—C19	114.3 (4)
C5—C4—H4	118.5	O5—C20—O4	122.6 (4)
C4—C5—H5	120.8	O5—C20—C19	123.1 (4)
C4—C5—C6	118.5 (2)	C20A—O4A—H4AA	109.5
C6—C5—H5	120.8	C15A—C14A—C13	121.1 (8)
C5—C6—H6	120.3	C15A—C14A—C19A	121.6 (9)
C5—C6—C7	119.3 (3)	C19A—C14A—C13	117.2 (8)
C7—C6—H6	120.3	C14A—C15A—H15A	120.5
C6—C7—H7	120.4	C14A—C15A—C16A	118.9 (11)
C6—C7—C8	119.1 (3)	C16A—C15A—H15A	120.5
C8—C7—H7	120.4	C15A—C16A—H16A	120.9
N1—C8—C7	121.8 (2)	C17A—C16A—C15A	118.2 (9)
N1—C8—C9	114.9 (2)	C17A—C16A—H16A	120.9
C7—C8—C9	123.3 (2)	C16A—C17A—H17A	118.1
N2—C9—C8	115.0 (2)	C18A—C17A—C16A	123.9 (9)
N2—C9—C10	122.5 (2)	C18A—C17A—H17A	118.1
C10—C9—C8	122.5 (2)	C17A—C18A—H18A	121.4
C9—C10—H10	120.4	C17A—C18A—C19A	117.1 (10)
C9—C10—C11	119.2 (2)	C19A—C18A—H18A	121.4
C11—C10—H10	120.4	C14A—C19A—C18A	119.8 (9)
C10—C11—H11	120.5	C14A—C19A—C20A	126.3 (9)
C12—C11—C10	118.9 (2)	C18A—C19A—C20A	113.8 (8)
C12—C11—H11	120.5	O4A—C20A—C19A	113.7 (9)
C11—C12—H12	120.3	O5A—C20A—O4A	120.0 (10)
C11—C12—C13	119.5 (2)	O5A—C20A—C19A	125.6 (11)
Mn1—N1—C4—C5	173.4 (2)	C12—C13—C14—C19	73.9 (4)
Mn1—N1—C8—C7	−173.9 (2)	C12—C13—C14A—C15A	72.9 (10)
Mn1—N1—C8—C9	6.8 (3)	C12—C13—C14A—C19A	−111.1 (7)
Mn1—N2—C9—C8	−9.8 (3)	C13—N2—C9—C8	176.6 (2)
Mn1—N2—C9—C10	170.4 (2)	C13—N2—C9—C10	−3.2 (4)
Mn1—N2—C13—C12	−168.8 (2)	C13—C14—C15—C16	177.1 (4)
Mn1—N2—C13—C14	21.9 (4)	C13—C14—C19—C18	−176.0 (3)
Mn1—N2—C13—C14A	−7.7 (6)	C13—C14—C19—C20	8.8 (5)
N1—C4—C5—C6	0.7 (4)	C13—C14A—C15A—C16A	−179.2 (9)
N1—C8—C9—N2	2.3 (3)	C13—C14A—C19A—C18A	−177.2 (8)
N1—C8—C9—C10	−178.0 (3)	C13—C14A—C19A—C20A	1.5 (15)
N2—C9—C10—C11	0.2 (5)	C14—C15—C16—C17	−2.5 (7)
N2—C13—C14—C15	69.6 (4)	C14—C19—C20—O4	6.6 (6)
N2—C13—C14—C19	−116.4 (3)	C14—C19—C20—O5	−173.5 (4)
N2—C13—C14A—C15A	−90.2 (10)	C15—C14—C19—C18	−2.1 (5)
N2—C13—C14A—C19A	85.7 (8)	C15—C14—C19—C20	−177.3 (4)
C4—N1—C8—C7	1.6 (4)	C15—C16—C17—C18	1.2 (7)
C4—N1—C8—C9	−177.7 (2)	C16—C17—C18—C19	−0.5 (7)
C4—C5—C6—C7	0.2 (5)	C17—C18—C19—C14	0.9 (6)
C5—C6—C7—C8	−0.2 (5)	C17—C18—C19—C20	176.6 (4)
C6—C7—C8—N1	−0.7 (4)	C18—C19—C20—O4	−168.7 (4)
C6—C7—C8—C9	178.5 (3)	C18—C19—C20—O5	11.2 (6)
C7—C8—C9—N2	−177.1 (3)	C19—C14—C15—C16	2.9 (7)
C7—C8—C9—C10	2.7 (4)	C14A—C15A—C16A—C17A	−2.7 (17)
C8—N1—C4—C5	−1.7 (4)	C14A—C19A—C20A—O4A	29 (2)
C8—C9—C10—C11	−179.6 (3)	C14A—C19A—C20A—O5A	−160.9 (15)
C9—N2—C13—C12	3.6 (4)	C15A—C14A—C19A—C18A	−1.3 (15)
C9—N2—C13—C14	−165.7 (3)	C15A—C14A—C19A—C20A	177.4 (13)
C9—N2—C13—C14A	164.7 (5)	C15A—C16A—C17A—C18A	−3.7 (17)
C9—C10—C11—C12	2.6 (5)	C16A—C17A—C18A—C19A	7.3 (17)
C10—C11—C12—C13	−2.2 (5)	C17A—C18A—C19A—C14A	−4.8 (15)
C11—C12—C13—N2	−1.0 (5)	C17A—C18A—C19A—C20A	176.4 (12)
C11—C12—C13—C14	168.0 (3)	C18A—C19A—C20A—O4A	−152.6 (12)
C11—C12—C13—C14A	−164.4 (5)	C18A—C19A—C20A—O5A	18 (2)
C12—C13—C14—C15	−100.1 (4)	C19A—C14A—C15A—C16A	5.0 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Br1^i	0.95	2.87	3.685 (3)	144

Symmetry code: (i) −x+1, −y+1, −z+1.

fac-[2-(2,2'-Bipyridin-6-yl)benzoic acid-κ²N,N']tricarbonylchloridorhenium(I) tetrahydrofuran monosolvate (II)

Crystal data

[ReCl(C17H12N2O2)(CO)3]·C4H8O	F(000) = 1272
Mr = 654.07	Dx = 1.867 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.462 (4) Å	Cell parameters from 9101 reflections
b = 11.370 (3) Å	θ = 2.6–31.8°
c = 13.370 (3) Å	µ = 5.38 mm^−1
β = 98.023 (10)°	T = 100 K
V = 2327.4 (10) Å^3	Block, yellow
Z = 4	0.28 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEXIII area detector diffractometer	7944 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	7361 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.027
Detector resolution: 7.9 pixels mm^-1	θmax = 31.9°, θmin = 1.3°
0.5° ω and 0.5° φ scans	h = −22→22
Absorption correction: analytical (SADABS; Krause et al., 2015)	k = −16→16
Tmin = 0.285, Tmax = 0.526	l = −19→19
70522 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)] = 0.016	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.039	w = 1/[σ^2(Fo^2) + (0.0182P)^2 + 2.0257P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.003
7944 reflections	Δρmax = 1.63 e Å^−3
342 parameters	Δρmin = −1.64 e Å^−3
27 restraints

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)
Re1	0.25443 (2)	0.56361 (2)	0.41243 (2)	0.01643 (2)
Cl1	0.12745 (2)	0.69931 (3)	0.37941 (3)	0.02075 (7)
O1	0.38542 (11)	0.75829 (16)	0.48236 (17)	0.0571 (5)
O2	0.31136 (12)	0.60610 (14)	0.20431 (13)	0.0469 (4)
O3	0.40094 (9)	0.38300 (14)	0.46361 (13)	0.0395 (3)
O4	0.25774 (8)	0.21703 (11)	0.31781 (9)	0.0263 (2)
O5	0.31281 (9)	0.16759 (12)	0.17689 (11)	0.0295 (3)
H5	0.339 (2)	0.111 (3)	0.218 (2)	0.064 (9)*
N1	0.20926 (9)	0.54664 (12)	0.55735 (10)	0.0189 (2)
N2	0.15082 (8)	0.42971 (10)	0.38837 (9)	0.0141 (2)
C1	0.33623 (12)	0.68554 (17)	0.45436 (17)	0.0336 (4)
C2	0.28734 (13)	0.58568 (16)	0.28011 (16)	0.0295 (4)
C3	0.34552 (11)	0.44986 (15)	0.44347 (15)	0.0260 (3)
C4	0.24129 (12)	0.60914 (17)	0.63982 (14)	0.0298 (4)
H4	0.2891	0.6606	0.6359	0.036*
C5	0.20740 (15)	0.6013 (2)	0.72977 (15)	0.0386 (5)
H5A	0.2321	0.6456	0.7870	0.046*
C6	0.13710 (14)	0.5282 (2)	0.73522 (13)	0.0365 (5)
H6	0.1123	0.5219	0.7961	0.044*
C7	0.10326 (12)	0.46437 (17)	0.65100 (13)	0.0271 (3)
H7	0.0542	0.4145	0.6530	0.033*
C8	0.14155 (10)	0.47363 (13)	0.56311 (11)	0.0178 (3)
C9	0.11021 (9)	0.40700 (13)	0.47062 (11)	0.0163 (2)
C10	0.04153 (11)	0.32791 (14)	0.46733 (14)	0.0256 (3)
H10	0.0159	0.3116	0.5264	0.031*
C11	0.01085 (12)	0.27318 (16)	0.37729 (17)	0.0313 (4)
H11	−0.0374	0.2207	0.3729	0.038*
C12	0.05092 (11)	0.29564 (15)	0.29444 (14)	0.0272 (3)
H12	0.0306	0.2587	0.2318	0.033*
C13	0.12151 (10)	0.37260 (13)	0.30166 (11)	0.0185 (3)
C14	0.15673 (11)	0.39961 (15)	0.20576 (12)	0.0236 (3)
C15	0.11602 (16)	0.4894 (2)	0.14585 (15)	0.0413 (5)
H15	0.0723	0.5356	0.1704	0.050*
C16	0.13830 (19)	0.5124 (2)	0.05091 (16)	0.0514 (7)
H16	0.1110	0.5752	0.0116	0.062*
C17	0.20068 (16)	0.4436 (2)	0.01340 (14)	0.0395 (5)
H17	0.2160	0.4589	−0.0518	0.047*
C18	0.24041 (12)	0.35285 (17)	0.07105 (12)	0.0274 (3)
H18	0.2825	0.3052	0.0448	0.033*
C19	0.21945 (10)	0.33025 (14)	0.16769 (12)	0.0206 (3)
C20	0.26432 (10)	0.23343 (14)	0.23004 (13)	0.0204 (3)
O6	0.4105 (3)	0.0039 (5)	0.2725 (3)	0.0444 (9)	0.672 (3)
C21	0.4761 (3)	−0.0296 (4)	0.2093 (3)	0.0412 (10)	0.672 (3)
H21A	0.5111	0.0390	0.1931	0.049*	0.672 (3)
H21B	0.4492	−0.0674	0.1458	0.049*	0.672 (3)
C22	0.5303 (3)	−0.1156 (4)	0.2774 (4)	0.0535 (11)	0.672 (3)
H22A	0.5900	−0.1222	0.2591	0.064*	0.672 (3)
H22B	0.5029	−0.1945	0.2737	0.064*	0.672 (3)
C23	0.5321 (2)	−0.0610 (4)	0.3845 (3)	0.0523 (11)	0.672 (3)
H23A	0.5304	−0.1234	0.4358	0.063*	0.672 (3)
H23B	0.5856	−0.0134	0.4028	0.063*	0.672 (3)
C24	0.4518 (3)	0.0153 (4)	0.3778 (3)	0.0467 (9)	0.672 (3)
H24A	0.4122	−0.0126	0.4249	0.056*	0.672 (3)
H24B	0.4678	0.0981	0.3940	0.056*	0.672 (3)
O6A	0.4080 (11)	−0.0019 (17)	0.2447 (7)	0.0339 (13)	0.202 (3)
C24A	0.4408 (8)	−0.0269 (14)	0.3488 (8)	0.0339 (13)	0.202 (3)
H24C	0.3953	−0.0664	0.3821	0.041*	0.202 (3)
H24D	0.4579	0.0469	0.3857	0.041*	0.202 (3)
C23A	0.5209 (7)	−0.1082 (11)	0.3488 (8)	0.0339 (13)	0.202 (3)
H23C	0.5763	−0.0639	0.3632	0.041*	0.202 (3)
H23D	0.5207	−0.1731	0.3981	0.041*	0.202 (3)
C22A	0.5060 (8)	−0.1537 (11)	0.2397 (8)	0.0339 (13)	0.202 (3)
H22C	0.5610	−0.1829	0.2184	0.041*	0.202 (3)
H22D	0.4617	−0.2171	0.2311	0.041*	0.202 (3)
C21A	0.4733 (14)	−0.0426 (17)	0.1815 (10)	0.0339 (13)	0.202 (3)
H21C	0.5206	0.0156	0.1796	0.041*	0.202 (3)
H21D	0.4461	−0.0610	0.1117	0.041*	0.202 (3)
O6B	0.4356 (8)	0.0219 (9)	0.2593 (10)	0.0298 (18)*	0.126 (3)
C21B	0.4661 (11)	−0.0418 (14)	0.1775 (7)	0.0298 (18)*	0.126 (3)
H21E	0.4967	0.0119	0.1359	0.036*	0.126 (3)
H21F	0.4164	−0.0783	0.1338	0.036*	0.126 (3)
C22B	0.5288 (9)	−0.1366 (12)	0.2266 (9)	0.0298 (18)*	0.126 (3)
H22E	0.5892	−0.1061	0.2424	0.036*	0.126 (3)
H22F	0.5288	−0.2068	0.1828	0.036*	0.126 (3)
C23B	0.4892 (9)	−0.1641 (9)	0.3233 (9)	0.0298 (18)*	0.126 (3)
H23E	0.4393	−0.2192	0.3098	0.036*	0.126 (3)
H23F	0.5333	−0.1975	0.3765	0.036*	0.126 (3)
C24B	0.4593 (9)	−0.0416 (11)	0.3526 (7)	0.0298 (18)*	0.126 (3)
H24E	0.4085	−0.0480	0.3899	0.036*	0.126 (3)
H24F	0.5071	−0.0007	0.3959	0.036*	0.126 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Re1	0.01365 (3)	0.01547 (3)	0.02146 (3)	−0.00104 (2)	0.00704 (2)	−0.00100 (2)
Cl1	0.02042 (15)	0.01814 (15)	0.02561 (17)	0.00341 (12)	0.00999 (12)	0.00509 (13)
O1	0.0344 (8)	0.0381 (9)	0.0991 (15)	−0.0196 (7)	0.0102 (9)	−0.0154 (9)
O2	0.0676 (11)	0.0336 (8)	0.0500 (9)	−0.0017 (7)	0.0453 (9)	0.0034 (7)
O3	0.0222 (6)	0.0359 (8)	0.0597 (10)	0.0097 (6)	0.0029 (6)	−0.0023 (7)
O4	0.0279 (6)	0.0249 (6)	0.0258 (6)	0.0039 (5)	0.0025 (5)	0.0017 (5)
O5	0.0250 (6)	0.0258 (6)	0.0395 (7)	0.0063 (5)	0.0105 (5)	−0.0027 (5)
N1	0.0201 (6)	0.0206 (6)	0.0159 (5)	0.0042 (5)	0.0022 (4)	−0.0032 (4)
N2	0.0152 (5)	0.0137 (5)	0.0142 (5)	0.0023 (4)	0.0046 (4)	0.0000 (4)
C1	0.0223 (8)	0.0249 (8)	0.0550 (12)	−0.0057 (7)	0.0106 (7)	−0.0059 (8)
C2	0.0330 (9)	0.0223 (7)	0.0385 (10)	0.0010 (6)	0.0234 (8)	0.0013 (7)
C3	0.0171 (7)	0.0261 (8)	0.0355 (9)	−0.0004 (6)	0.0062 (6)	−0.0043 (6)
C4	0.0297 (8)	0.0322 (9)	0.0258 (8)	0.0064 (7)	−0.0017 (6)	−0.0135 (7)
C5	0.0413 (11)	0.0496 (12)	0.0227 (8)	0.0188 (9)	−0.0034 (7)	−0.0165 (8)
C6	0.0434 (11)	0.0513 (12)	0.0160 (7)	0.0246 (10)	0.0085 (7)	0.0002 (7)
C7	0.0334 (9)	0.0310 (8)	0.0196 (7)	0.0122 (7)	0.0128 (6)	0.0070 (6)
C8	0.0215 (6)	0.0177 (6)	0.0151 (6)	0.0060 (5)	0.0061 (5)	0.0019 (5)
C9	0.0169 (6)	0.0148 (6)	0.0185 (6)	0.0019 (5)	0.0069 (5)	0.0013 (5)
C10	0.0230 (7)	0.0198 (7)	0.0370 (9)	−0.0019 (6)	0.0148 (6)	0.0016 (6)
C11	0.0215 (7)	0.0208 (7)	0.0525 (11)	−0.0063 (6)	0.0084 (7)	−0.0063 (7)
C12	0.0235 (7)	0.0229 (7)	0.0339 (9)	−0.0003 (6)	−0.0002 (6)	−0.0115 (6)
C13	0.0188 (6)	0.0177 (6)	0.0185 (6)	0.0043 (5)	0.0015 (5)	−0.0038 (5)
C14	0.0287 (8)	0.0259 (7)	0.0159 (6)	0.0078 (6)	0.0021 (6)	−0.0033 (6)
C15	0.0574 (13)	0.0442 (11)	0.0242 (9)	0.0312 (10)	0.0117 (8)	0.0077 (8)
C16	0.0722 (17)	0.0596 (15)	0.0237 (9)	0.0390 (14)	0.0119 (10)	0.0149 (9)
C17	0.0532 (13)	0.0509 (13)	0.0155 (7)	0.0185 (10)	0.0084 (8)	0.0037 (7)
C18	0.0319 (8)	0.0321 (9)	0.0182 (7)	0.0052 (7)	0.0037 (6)	−0.0051 (6)
C19	0.0226 (7)	0.0208 (7)	0.0176 (6)	0.0031 (5)	0.0004 (5)	−0.0046 (5)
C20	0.0148 (6)	0.0188 (6)	0.0273 (7)	−0.0012 (5)	0.0013 (5)	−0.0033 (6)
O6	0.0276 (13)	0.0409 (15)	0.061 (2)	0.0138 (11)	−0.0072 (19)	0.001 (2)
C21	0.0222 (14)	0.0421 (19)	0.058 (3)	0.0132 (13)	0.001 (2)	0.009 (2)
C22	0.0369 (19)	0.053 (2)	0.071 (3)	0.0202 (18)	0.010 (2)	0.022 (2)
C23	0.0303 (16)	0.080 (3)	0.049 (2)	0.0020 (18)	0.0129 (16)	0.028 (2)
C24	0.046 (2)	0.044 (2)	0.048 (2)	−0.0090 (17)	0.0000 (17)	0.0119 (17)
O6A	0.032 (3)	0.049 (3)	0.020 (2)	0.007 (2)	0.0013 (19)	0.008 (2)
C24A	0.032 (3)	0.049 (3)	0.020 (2)	0.007 (2)	0.0013 (19)	0.008 (2)
C23A	0.032 (3)	0.049 (3)	0.020 (2)	0.007 (2)	0.0013 (19)	0.008 (2)
C22A	0.032 (3)	0.049 (3)	0.020 (2)	0.007 (2)	0.0013 (19)	0.008 (2)
C21A	0.032 (3)	0.049 (3)	0.020 (2)	0.007 (2)	0.0013 (19)	0.008 (2)

Geometric parameters (Å, º)

Re1—Cl1	2.4875 (6)	C18—C19	1.399 (2)
Re1—N1	2.1580 (14)	C19—C20	1.492 (2)
Re1—N2	2.2008 (13)	O6—C21	1.458 (5)
Re1—C1	1.9074 (19)	O6—C24	1.469 (5)
Re1—C2	1.9244 (19)	C21—H21A	0.9900
Re1—C3	1.9146 (18)	C21—H21B	0.9900
O1—C1	1.150 (2)	C21—C22	1.508 (5)
O2—C2	1.151 (2)	C22—H22A	0.9900
O3—C3	1.149 (2)	C22—H22B	0.9900
O4—C20	1.206 (2)	C22—C23	1.558 (7)
O5—H5	0.90 (3)	C23—H23A	0.9900
O5—C20	1.333 (2)	C23—H23B	0.9900
N1—C4	1.347 (2)	C23—C24	1.507 (5)
N1—C8	1.347 (2)	C24—H24A	0.9900
N2—C9	1.3648 (18)	C24—H24B	0.9900
N2—C13	1.3506 (19)	O6A—C24A	1.441 (11)
C4—H4	0.9500	O6A—C21A	1.478 (13)
C4—C5	1.380 (3)	C24A—H24C	0.9900
C5—H5A	0.9500	C24A—H24D	0.9900
C5—C6	1.378 (4)	C24A—C23A	1.546 (12)
C6—H6	0.9500	C23A—H23C	0.9900
C6—C7	1.380 (3)	C23A—H23D	0.9900
C7—H7	0.9500	C23A—C22A	1.534 (13)
C7—C8	1.392 (2)	C22A—H22C	0.9900
C8—C9	1.473 (2)	C22A—H22D	0.9900
C9—C10	1.388 (2)	C22A—C21A	1.533 (13)
C10—H10	0.9500	C21A—H21C	0.9900
C10—C11	1.379 (3)	C21A—H21D	0.9900
C11—H11	0.9500	O6B—C21B	1.4432
C11—C12	1.367 (3)	O6B—C24B	1.4435
C12—H12	0.9500	C21B—H21E	0.9900
C12—C13	1.392 (2)	C21B—H21F	0.9900
C13—C14	1.493 (2)	C21B—C22B	1.5350
C14—C15	1.393 (2)	C22B—H22E	0.9900
C14—C19	1.400 (2)	C22B—H22F	0.9900
C15—H15	0.9500	C22B—C23B	1.5390
C15—C16	1.386 (3)	C23B—H23E	0.9900
C16—H16	0.9500	C23B—H23F	0.9900
C16—C17	1.389 (3)	C23B—C24B	1.5350
C17—H17	0.9500	C24B—H24E	0.9900
C17—C18	1.380 (3)	C24B—H24F	0.9900
C18—H18	0.9500
N1—Re1—Cl1	82.45 (4)	C21—O6—C24	109.5 (3)
N1—Re1—N2	75.48 (5)	O6—C21—H21A	111.6
N2—Re1—Cl1	82.11 (4)	O6—C21—H21B	111.6
C1—Re1—Cl1	94.36 (6)	O6—C21—C22	101.1 (3)
C1—Re1—N1	94.91 (8)	H21A—C21—H21B	109.4
C1—Re1—N2	170.08 (7)	C22—C21—H21A	111.6
C1—Re1—C2	85.75 (9)	C22—C21—H21B	111.6
C1—Re1—C3	89.41 (8)	C21—C22—H22A	111.1
C2—Re1—Cl1	93.41 (6)	C21—C22—H22B	111.1
C2—Re1—N1	175.84 (7)	C21—C22—C23	103.5 (3)
C2—Re1—N2	103.67 (7)	H22A—C22—H22B	109.0
C3—Re1—Cl1	174.86 (5)	C23—C22—H22A	111.1
C3—Re1—N1	93.76 (7)	C23—C22—H22B	111.1
C3—Re1—N2	93.61 (6)	C22—C23—H23A	110.7
C3—Re1—C2	90.36 (8)	C22—C23—H23B	110.7
C20—O5—H5	109 (2)	H23A—C23—H23B	108.8
C4—N1—Re1	124.05 (13)	C24—C23—C22	105.4 (3)
C8—N1—Re1	117.26 (10)	C24—C23—H23A	110.7
C8—N1—C4	118.58 (15)	C24—C23—H23B	110.7
C9—N2—Re1	114.86 (10)	O6—C24—C23	104.5 (4)
C13—N2—Re1	127.46 (10)	O6—C24—H24A	110.8
C13—N2—C9	117.63 (13)	O6—C24—H24B	110.8
O1—C1—Re1	178.1 (2)	C23—C24—H24A	110.8
O2—C2—Re1	174.45 (19)	C23—C24—H24B	110.8
O3—C3—Re1	178.65 (18)	H24A—C24—H24B	108.9
N1—C4—H4	118.7	C24A—O6A—C21A	108.4 (10)
N1—C4—C5	122.6 (2)	O6A—C24A—H24C	110.3
C5—C4—H4	118.7	O6A—C24A—H24D	110.3
C4—C5—H5A	120.6	O6A—C24A—C23A	106.9 (9)
C6—C5—C4	118.87 (18)	H24C—C24A—H24D	108.6
C6—C5—H5A	120.6	C23A—C24A—H24C	110.3
C5—C6—H6	120.5	C23A—C24A—H24D	110.3
C5—C6—C7	119.08 (17)	C24A—C23A—H23C	111.6
C7—C6—H6	120.5	C24A—C23A—H23D	111.6
C6—C7—H7	120.3	H23C—C23A—H23D	109.4
C6—C7—C8	119.45 (19)	C22A—C23A—C24A	100.9 (8)
C8—C7—H7	120.3	C22A—C23A—H23C	111.6
N1—C8—C7	121.38 (15)	C22A—C23A—H23D	111.6
N1—C8—C9	115.86 (13)	C23A—C22A—H22C	111.5
C7—C8—C9	122.76 (15)	C23A—C22A—H22D	111.5
N2—C9—C8	116.40 (13)	H22C—C22A—H22D	109.3
N2—C9—C10	122.22 (14)	C21A—C22A—C23A	101.5 (9)
C10—C9—C8	121.36 (14)	C21A—C22A—H22C	111.5
C9—C10—H10	120.4	C21A—C22A—H22D	111.5
C11—C10—C9	119.24 (16)	O6A—C21A—C22A	99.9 (11)
C11—C10—H10	120.4	O6A—C21A—H21C	111.8
C10—C11—H11	120.5	O6A—C21A—H21D	111.8
C12—C11—C10	118.92 (16)	C22A—C21A—H21C	111.8
C12—C11—H11	120.5	C22A—C21A—H21D	111.8
C11—C12—H12	120.0	H21C—C21A—H21D	109.5
C11—C12—C13	120.07 (16)	C21B—O6B—C24B	109.5
C13—C12—H12	120.0	O6B—C21B—H21E	110.4
N2—C13—C12	121.85 (15)	O6B—C21B—H21F	110.4
N2—C13—C14	121.29 (14)	O6B—C21B—C22B	106.4
C12—C13—C14	116.49 (14)	H21E—C21B—H21F	108.6
C15—C14—C13	117.06 (15)	C22B—C21B—H21E	110.4
C15—C14—C19	118.97 (16)	C22B—C21B—H21F	110.4
C19—C14—C13	123.40 (15)	C21B—C22B—H22E	111.5
C14—C15—H15	119.5	C21B—C22B—H22F	111.5
C16—C15—C14	121.01 (18)	C21B—C22B—C23B	101.5
C16—C15—H15	119.5	H22E—C22B—H22F	109.3
C15—C16—H16	120.1	C23B—C22B—H22E	111.5
C15—C16—C17	119.87 (19)	C23B—C22B—H22F	111.5
C17—C16—H16	120.1	C22B—C23B—H23E	111.5
C16—C17—H17	120.1	C22B—C23B—H23F	111.5
C18—C17—C16	119.80 (18)	H23E—C23B—H23F	109.3
C18—C17—H17	120.1	C24B—C23B—C22B	101.5
C17—C18—H18	119.6	C24B—C23B—H23E	111.5
C17—C18—C19	120.72 (17)	C24B—C23B—H23F	111.5
C19—C18—H18	119.6	O6B—C24B—C23B	106.4
C14—C19—C20	120.28 (14)	O6B—C24B—H24E	110.4
C18—C19—C14	119.60 (15)	O6B—C24B—H24F	110.4
C18—C19—C20	120.12 (15)	C23B—C24B—H24E	110.4
O4—C20—O5	124.18 (16)	C23B—C24B—H24F	110.4
O4—C20—C19	124.17 (15)	H24E—C24B—H24F	108.6
O5—C20—C19	111.64 (14)
Re1—N1—C4—C5	175.99 (14)	C13—N2—C9—C10	0.4 (2)
Re1—N1—C8—C7	−174.60 (12)	C13—C14—C15—C16	−173.3 (2)
Re1—N1—C8—C9	4.26 (17)	C13—C14—C19—C18	171.61 (16)
Re1—N2—C9—C8	−0.54 (16)	C13—C14—C19—C20	−8.9 (2)
Re1—N2—C9—C10	177.80 (12)	C14—C15—C16—C17	1.5 (4)
Re1—N2—C13—C12	−175.22 (11)	C14—C19—C20—O4	−8.5 (2)
Re1—N2—C13—C14	−2.4 (2)	C14—C19—C20—O5	171.69 (15)
N1—C4—C5—C6	−1.1 (3)	C15—C14—C19—C18	0.5 (3)
N1—C8—C9—N2	−2.41 (19)	C15—C14—C19—C20	179.93 (18)
N1—C8—C9—C10	179.23 (14)	C15—C16—C17—C18	−0.2 (4)
N2—C9—C10—C11	−2.4 (2)	C16—C17—C18—C19	−0.9 (4)
N2—C13—C14—C15	−88.2 (2)	C17—C18—C19—C14	0.8 (3)
N2—C13—C14—C19	100.55 (19)	C17—C18—C19—C20	−178.70 (18)
C4—N1—C8—C7	1.7 (2)	C18—C19—C20—O4	170.91 (16)
C4—N1—C8—C9	−179.42 (14)	C18—C19—C20—O5	−8.9 (2)
C4—C5—C6—C7	0.6 (3)	C19—C14—C15—C16	−1.6 (4)
C5—C6—C7—C8	1.0 (3)	O6—C21—C22—C23	−37.5 (4)
C6—C7—C8—N1	−2.2 (2)	C21—O6—C24—C23	−24.1 (5)
C6—C7—C8—C9	179.01 (15)	C21—C22—C23—C24	24.2 (4)
C7—C8—C9—N2	176.43 (14)	C22—C23—C24—O6	−1.0 (5)
C7—C8—C9—C10	−1.9 (2)	C24—O6—C21—C22	39.3 (5)
C8—N1—C4—C5	−0.1 (3)	O6A—C24A—C23A—C22A	−18.3 (16)
C8—C9—C10—C11	175.90 (15)	C24A—O6A—C21A—C22A	36.3 (19)
C9—N2—C13—C12	1.8 (2)	C24A—C23A—C22A—C21A	39.9 (14)
C9—N2—C13—C14	174.62 (13)	C23A—C22A—C21A—O6A	−46.9 (16)
C9—C10—C11—C12	2.1 (3)	C21A—O6A—C24A—C23A	−11.4 (19)
C10—C11—C12—C13	0.0 (3)	O6B—C21B—C22B—C23B	31.5
C11—C12—C13—N2	−2.1 (2)	C21B—O6B—C24B—C23B	−12.4
C11—C12—C13—C14	−175.19 (16)	C21B—C22B—C23B—C24B	−37.4
C12—C13—C14—C15	85.0 (2)	C22B—C23B—C24B—O6B	31.5
C12—C13—C14—C19	−86.3 (2)	C24B—O6B—C21B—C22B	−12.3
C13—N2—C9—C8	−177.94 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O6	0.90 (3)	1.74 (4)	2.615 (4)	164 (3)
O5—H5···O6A	0.90 (3)	1.68 (4)	2.516 (15)	154 (3)
O5—H5···O6B	0.90 (3)	1.83 (4)	2.642 (9)	150 (3)
C5—H5A···Cl1^i	0.95	2.80	3.371 (2)	120
C10—H10···Cl1^ii	0.95	2.70	3.552 (2)	149
C12—H12···Cl1^iii	0.95	2.76	3.524 (2)	138

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