Crystal structures and Hirshfeld surface analysis of [κ²-P,N-{(C₆H₅)₂(C₅H₅N)P}Re(CO)₃Br]·2CHCl₃ and the product of its reaction with piperidine, [P-{(C₆H₅)₂(C₅H₅N)P}(C₅H₁₁N)Re(CO)₃Br]

The reaction of the ligand di­pyridyl­phosphine with (Re(CO)₃(OC₄H₈)Br)₂ followed by crystallization in chloro­form leads to [κ²-P,N-{(C₆H₅)₂(C₅H₅N)P}Re(CO)₃Br]·2CHCl₃. Reaction of this complex with piperidine leads to partial decoordination of the 2-pyridyl­phosphine in the product, [P-{(C₆H₅)₂(C₅H₅N)P}(C₅H₁₁N)Re(CO)₃Br], which displays an intra­molecular hydrogen bond between the piperidine aminic hydrogen atom and the uncoordinated pyridyl group, with D...A = 2.992 (9) Å.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.007 Å
• Mean [sigma](C-C) = 0.012 Å
• R factor = 0.026
• wR factor = 0.065
• Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Datablock: I-2CHCl3



Alert level C
PLAT244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of        C21 Check
PLAT244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of        C22 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including       Cl4      0.115 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          7 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT230_ALERT_2_G Hirshfeld Test Diff for    O2       --C2       .        5.3 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Re1      --Br1      .        8.7 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Re1      --C2       .        7.0 s.u.
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          8 Note

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: II


Alert level C
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0117 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.253 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          9 Report
PLAT977_ALERT_2_C Check Negative Difference Density on H16              -0.38 eA-3
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2 Note
PLAT014_ALERT_1_G N.O.K.   _shelx_fab_checksum Found in CIF ......     Please Check
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large       9.47 Why ?
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT605_ALERT_4_G Largest Solvent Accessible VOID in the Structure         83 A   3  
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT869_ALERT_4_G ALERTS Related to the Use of SQUEEZE Suppressed           ! Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          6 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          8 Note

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

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


checkCIF publication errors

Alert level A
PUBL022_ALERT_1_A There is a mismatched ~ on line 408
              I\\\\\\\\\\\\\\\\cdot2CHCl\\\\\\\~3\\\\\\\~
              If you require a ~ then it should be escaped
              with a \, i.e. \~
              Otherwise there must be a matching closing ~, e.g. C~2~H~4~

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

---

Computing details

For both structures, data collection: SMART (Bruker, 2012); cell refinement: SMART (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Bromidotricarbonyl[diphenyl(pyridin-2-yl)phosphane-κ²N,P]rhenium(I) chloroform disolvate, [ReBr(C₁₇H₁₄NP)(CO)₃]·2CHCl₃ (I-2CHCl3)

Crystal data

[ReBr(C17H14NP)(CO)3]·2CHCl3	F(000) = 1624
Mr = 852.14	Dx = 1.995 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.194 (4) Å	Cell parameters from 6313 reflections
b = 12.314 (4) Å	θ = 2.5–28.5°
c = 16.249 (5) Å	µ = 6.34 mm^−1
β = 92.701 (4)°	T = 150 K
V = 2836.7 (15) Å^3	Block, yellow
Z = 4	0.16 × 0.13 × 0.05 mm

Data collection

Bruker SMART CCD area detector diffractometer	4526 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.048
phi and ω scans	θmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −17→17
Tmin = 0.386, Tmax = 0.746	k = −15→15
19979 measured reflections	l = −19→20
5550 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.026	H-atom parameters constrained
wR(F^2) = 0.065	w = 1/[σ^2(Fo^2)] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max < 0.001
5550 reflections	Δρmax = 0.39 e Å^−3
317 parameters	Δρmin = −0.35 e Å^−3
0 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00027 (8)

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
Re1	0.29082 (2)	0.42455 (2)	0.08046 (2)	0.06954 (7)
Br1	0.45807 (3)	0.36073 (4)	0.13313 (3)	0.07781 (13)
P1	0.25501 (8)	0.23375 (8)	0.04434 (7)	0.0705 (3)
N1	0.3373 (3)	0.3742 (3)	−0.0392 (2)	0.0722 (9)
C1	0.2470 (3)	0.4367 (3)	0.1897 (3)	0.0742 (11)
O1	0.2190 (3)	0.4391 (3)	0.2547 (2)	0.0860 (9)
C2	0.1733 (4)	0.4761 (3)	0.0367 (3)	0.0779 (11)
O2	0.1045 (3)	0.5103 (3)	0.0100 (2)	0.0879 (9)
C3	0.3368 (4)	0.5732 (4)	0.0793 (3)	0.0792 (11)
O3	0.3635 (3)	0.6583 (3)	0.0772 (2)	0.0949 (10)
C4	0.3826 (3)	0.4234 (4)	−0.0986 (3)	0.0783 (11)
H4	0.3974	0.4967	−0.0932	0.094*
C5	0.4076 (4)	0.3694 (4)	−0.1669 (3)	0.0861 (13)
H5	0.4382	0.4061	−0.2079	0.103*
C6	0.3879 (4)	0.2598 (4)	−0.1759 (3)	0.0855 (13)
H6	0.4053	0.2222	−0.2224	0.103*
C7	0.3422 (3)	0.2081 (4)	−0.1148 (3)	0.0792 (11)
H7	0.3283	0.1344	−0.1189	0.095*
C8	0.3171 (3)	0.2667 (3)	−0.0476 (3)	0.0701 (10)
C9	0.3085 (3)	0.1116 (3)	0.0857 (3)	0.0735 (11)
C10	0.4032 (4)	0.0890 (3)	0.0778 (3)	0.0788 (12)
H10	0.4404	0.1362	0.0486	0.095*
C11	0.4429 (4)	−0.0041 (4)	0.1134 (3)	0.0860 (13)
H11	0.5066	−0.0187	0.1080	0.103*
C12	0.3890 (4)	−0.0741 (4)	0.1561 (3)	0.0896 (14)
H12	0.4161	−0.1365	0.1793	0.108*
C13	0.2950 (4)	−0.0530 (4)	0.1651 (3)	0.0873 (14)
H13	0.2586	−0.1006	0.1946	0.105*
C14	0.2549 (4)	0.0392 (4)	0.1300 (3)	0.0812 (12)
H14	0.1912	0.0532	0.1360	0.097*
C15	0.1366 (3)	0.1951 (3)	0.0108 (3)	0.0723 (10)
C16	0.1182 (4)	0.1207 (4)	−0.0506 (3)	0.0830 (12)
H16	0.1680	0.0861	−0.0750	0.100*
C17	0.0272 (4)	0.0967 (4)	−0.0765 (3)	0.0912 (14)
H17	0.0156	0.0465	−0.1185	0.109*
C18	−0.0466 (4)	0.1470 (4)	−0.0402 (4)	0.0987 (16)
H18	−0.1084	0.1319	−0.0583	0.118*
C19	−0.0293 (4)	0.2190 (4)	0.0223 (4)	0.1030 (17)
H19	−0.0794	0.2512	0.0480	0.124*
C20	0.0622 (4)	0.2446 (4)	0.0478 (4)	0.0910 (14)
H20	0.0736	0.2950	0.0897	0.109*
C21	0.3309 (4)	0.7174 (4)	0.3787 (3)	0.0853 (13)
H21	0.3903	0.7468	0.4026	0.102*
Cl1	0.24667 (11)	0.82254 (11)	0.37214 (10)	0.1001 (4)
Cl2	0.29219 (12)	0.61431 (11)	0.44304 (10)	0.1061 (4)
Cl3	0.35045 (12)	0.66739 (12)	0.28107 (9)	0.1034 (4)
C22	0.0251 (4)	0.0957 (4)	0.3284 (4)	0.0959 (15)
H22	0.0155	0.1018	0.3876	0.115*
Cl4	0.02810 (13)	−0.04155 (12)	0.30240 (11)	0.1102 (4)
Cl5	0.13277 (12)	0.15706 (16)	0.30768 (12)	0.1288 (6)
Cl6	−0.06727 (13)	0.16078 (13)	0.27497 (13)	0.1261 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Re1	0.06848 (12)	0.06853 (9)	0.07162 (11)	0.00019 (7)	0.00347 (7)	0.00016 (7)
Br1	0.0707 (3)	0.0804 (2)	0.0822 (3)	−0.00035 (19)	0.0024 (2)	0.0055 (2)
P1	0.0706 (7)	0.0695 (5)	0.0717 (7)	0.0009 (5)	0.0046 (5)	−0.0012 (5)
N1	0.069 (2)	0.0740 (18)	0.074 (2)	0.0018 (16)	0.0066 (17)	0.0004 (16)
C1	0.071 (3)	0.071 (2)	0.079 (3)	−0.0012 (19)	−0.005 (2)	0.000 (2)
O1	0.088 (2)	0.097 (2)	0.074 (2)	0.0047 (17)	0.0056 (17)	−0.0020 (16)
C2	0.088 (3)	0.070 (2)	0.077 (3)	0.000 (2)	0.012 (2)	−0.003 (2)
O2	0.078 (2)	0.092 (2)	0.092 (2)	0.0048 (17)	−0.0031 (18)	0.0046 (17)
C3	0.083 (3)	0.079 (2)	0.074 (3)	0.005 (2)	−0.006 (2)	−0.005 (2)
O3	0.111 (3)	0.0759 (18)	0.097 (3)	−0.0122 (18)	0.000 (2)	0.0000 (16)
C4	0.073 (3)	0.080 (2)	0.083 (3)	0.002 (2)	0.009 (2)	0.008 (2)
C5	0.076 (3)	0.099 (3)	0.083 (3)	0.002 (2)	0.013 (2)	0.010 (2)
C6	0.080 (3)	0.100 (3)	0.077 (3)	0.005 (2)	0.007 (2)	−0.002 (2)
C7	0.074 (3)	0.083 (2)	0.081 (3)	−0.001 (2)	0.002 (2)	−0.006 (2)
C8	0.064 (3)	0.071 (2)	0.074 (3)	0.0006 (17)	0.001 (2)	0.0005 (18)
C9	0.080 (3)	0.071 (2)	0.069 (3)	−0.0015 (19)	0.002 (2)	−0.0065 (18)
C10	0.080 (3)	0.071 (2)	0.085 (3)	0.001 (2)	−0.003 (2)	−0.003 (2)
C11	0.083 (3)	0.079 (2)	0.095 (4)	0.011 (2)	−0.005 (3)	−0.004 (2)
C12	0.101 (4)	0.076 (2)	0.090 (3)	0.006 (3)	−0.010 (3)	−0.002 (2)
C13	0.104 (4)	0.077 (2)	0.079 (3)	−0.003 (2)	−0.005 (3)	0.008 (2)
C14	0.081 (3)	0.081 (2)	0.082 (3)	0.003 (2)	0.003 (2)	−0.001 (2)
C15	0.072 (3)	0.0675 (19)	0.078 (3)	−0.0029 (18)	0.004 (2)	0.0041 (18)
C16	0.080 (3)	0.087 (3)	0.083 (3)	−0.010 (2)	0.006 (2)	0.000 (2)
C17	0.087 (4)	0.100 (3)	0.087 (4)	−0.015 (3)	0.001 (3)	0.000 (3)
C18	0.078 (4)	0.093 (3)	0.123 (5)	−0.014 (3)	−0.009 (3)	0.010 (3)
C19	0.073 (4)	0.090 (3)	0.146 (5)	−0.003 (3)	0.014 (3)	−0.006 (3)
C20	0.079 (3)	0.081 (3)	0.115 (4)	−0.003 (2)	0.018 (3)	−0.013 (3)
C21	0.085 (3)	0.088 (3)	0.084 (3)	−0.008 (2)	0.007 (3)	0.006 (2)
Cl1	0.1005 (10)	0.0898 (7)	0.1106 (10)	0.0026 (6)	0.0119 (8)	0.0115 (7)
Cl2	0.1271 (13)	0.0897 (7)	0.1023 (10)	−0.0028 (7)	0.0146 (9)	0.0158 (7)
Cl3	0.1147 (11)	0.1028 (8)	0.0938 (9)	−0.0140 (8)	0.0153 (8)	−0.0114 (7)
C22	0.087 (4)	0.108 (3)	0.092 (4)	−0.008 (3)	−0.001 (3)	−0.006 (3)
Cl4	0.1192 (12)	0.1039 (8)	0.1067 (11)	0.0020 (8)	−0.0035 (9)	0.0022 (8)
Cl5	0.1014 (12)	0.1516 (14)	0.1350 (14)	−0.0353 (10)	0.0217 (10)	−0.0418 (11)
Cl6	0.1167 (13)	0.1064 (9)	0.1519 (16)	−0.0004 (9)	−0.0286 (11)	0.0013 (9)

Geometric parameters (Å, º)

Re1—C2	1.892 (6)	C11—C12	1.364 (7)
Re1—C1	1.914 (5)	C11—H11	0.9300
Re1—C3	1.943 (5)	C12—C13	1.373 (8)
Re1—N1	2.173 (4)	C12—H12	0.9300
Re1—P1	2.4687 (13)	C13—C14	1.382 (6)
Re1—Br1	2.6066 (8)	C13—H13	0.9300
P1—C9	1.800 (5)	C14—H14	0.9300
P1—C15	1.806 (5)	C15—C16	1.370 (6)
P1—C8	1.815 (5)	C15—C20	1.382 (6)
N1—C4	1.330 (5)	C16—C17	1.371 (7)
N1—C8	1.360 (5)	C16—H16	0.9300
C1—O1	1.147 (5)	C17—C18	1.374 (8)
C2—O2	1.131 (6)	C17—H17	0.9300
C3—O3	1.116 (5)	C18—C19	1.362 (8)
C4—C5	1.355 (7)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.381 (8)
C5—C6	1.384 (7)	C19—H19	0.9300
C5—H5	0.9300	C20—H20	0.9300
C6—C7	1.368 (7)	C21—Cl3	1.737 (5)
C6—H6	0.9300	C21—Cl2	1.749 (5)
C7—C8	1.370 (6)	C21—Cl1	1.762 (5)
C7—H7	0.9300	C21—H21	0.9800
C9—C10	1.385 (6)	C22—Cl6	1.735 (6)
C9—C14	1.394 (6)	C22—Cl4	1.743 (6)
C10—C11	1.392 (6)	C22—Cl5	1.751 (6)
C10—H10	0.9300	C22—H22	0.9800
C2—Re1—C1	90.2 (2)	C9—C10—C11	120.2 (5)
C2—Re1—C3	88.3 (2)	C9—C10—H10	119.9
C1—Re1—C3	93.39 (19)	C11—C10—H10	119.9
C2—Re1—N1	93.39 (17)	C12—C11—C10	120.5 (5)
C1—Re1—N1	167.89 (15)	C12—C11—H11	119.8
C3—Re1—N1	98.27 (17)	C10—C11—H11	119.8
C2—Re1—P1	93.56 (13)	C11—C12—C13	120.3 (5)
C1—Re1—P1	102.86 (12)	C11—C12—H12	119.9
C3—Re1—P1	163.62 (15)	C13—C12—H12	119.9
N1—Re1—P1	65.39 (9)	C12—C13—C14	119.8 (5)
C2—Re1—Br1	176.20 (14)	C12—C13—H13	120.1
C1—Re1—Br1	92.84 (14)	C14—C13—H13	120.1
C3—Re1—Br1	89.22 (15)	C13—C14—C9	120.9 (5)
N1—Re1—Br1	84.11 (10)	C13—C14—H14	119.5
P1—Re1—Br1	88.01 (3)	C9—C14—H14	119.5
C9—P1—C15	105.2 (2)	C16—C15—C20	119.2 (5)
C9—P1—C8	106.3 (2)	C16—C15—P1	122.6 (4)
C15—P1—C8	106.9 (2)	C20—C15—P1	118.2 (4)
C9—P1—Re1	128.88 (16)	C15—C16—C17	120.8 (5)
C15—P1—Re1	120.04 (14)	C15—C16—H16	119.6
C8—P1—Re1	83.14 (13)	C17—C16—H16	119.6
C4—N1—C8	118.5 (4)	C16—C17—C18	119.8 (5)
C4—N1—Re1	134.2 (3)	C16—C17—H17	120.1
C8—N1—Re1	107.2 (3)	C18—C17—H17	120.1
O1—C1—Re1	176.7 (4)	C19—C18—C17	119.9 (5)
O2—C2—Re1	177.7 (4)	C19—C18—H18	120.1
O3—C3—Re1	178.8 (5)	C17—C18—H18	120.1
N1—C4—C5	121.7 (4)	C18—C19—C20	120.5 (5)
N1—C4—H4	119.2	C18—C19—H19	119.8
C5—C4—H4	119.2	C20—C19—H19	119.8
C4—C5—C6	120.3 (5)	C19—C20—C15	119.7 (5)
C4—C5—H5	119.8	C19—C20—H20	120.1
C6—C5—H5	119.8	C15—C20—H20	120.1
C7—C6—C5	118.6 (5)	Cl3—C21—Cl2	110.9 (3)
C7—C6—H6	120.7	Cl3—C21—Cl1	110.0 (3)
C5—C6—H6	120.7	Cl2—C21—Cl1	109.8 (3)
C6—C7—C8	118.9 (4)	Cl3—C21—H21	108.7
C6—C7—H7	120.6	Cl2—C21—H21	108.7
C8—C7—H7	120.6	Cl1—C21—H21	108.7
N1—C8—C7	122.0 (4)	Cl6—C22—Cl4	110.7 (3)
N1—C8—P1	104.1 (3)	Cl6—C22—Cl5	110.5 (3)
C7—C8—P1	133.9 (3)	Cl4—C22—Cl5	109.9 (3)
C10—C9—C14	118.4 (4)	Cl6—C22—H22	108.6
C10—C9—P1	121.8 (3)	Cl4—C22—H22	108.6
C14—C9—P1	119.7 (4)	Cl5—C22—H22	108.6
C8—N1—C4—C5	0.8 (7)	C14—C9—C10—C11	0.1 (7)
Re1—N1—C4—C5	176.3 (4)	P1—C9—C10—C11	177.4 (4)
N1—C4—C5—C6	−1.2 (8)	C9—C10—C11—C12	0.2 (8)
C4—C5—C6—C7	0.5 (8)	C10—C11—C12—C13	−0.5 (8)
C5—C6—C7—C8	0.4 (7)	C11—C12—C13—C14	0.5 (8)
C4—N1—C8—C7	0.2 (7)	C12—C13—C14—C9	−0.2 (8)
Re1—N1—C8—C7	−176.4 (4)	C10—C9—C14—C13	−0.1 (7)
C4—N1—C8—P1	−179.2 (3)	P1—C9—C14—C13	−177.5 (4)
Re1—N1—C8—P1	4.2 (3)	C9—P1—C15—C16	−63.3 (4)
C6—C7—C8—N1	−0.8 (7)	C8—P1—C15—C16	49.5 (4)
C6—C7—C8—P1	178.3 (4)	Re1—P1—C15—C16	141.4 (3)
C9—P1—C8—N1	−132.1 (3)	C9—P1—C15—C20	118.0 (4)
C15—P1—C8—N1	115.8 (3)	C8—P1—C15—C20	−129.2 (4)
Re1—P1—C8—N1	−3.5 (3)	Re1—P1—C15—C20	−37.3 (4)
C9—P1—C8—C7	48.6 (5)	C20—C15—C16—C17	1.3 (7)
C15—P1—C8—C7	−63.4 (5)	P1—C15—C16—C17	−177.4 (4)
Re1—P1—C8—C7	177.2 (5)	C15—C16—C17—C18	−0.5 (8)
C15—P1—C9—C10	145.3 (4)	C16—C17—C18—C19	−1.2 (9)
C8—P1—C9—C10	32.1 (4)	C17—C18—C19—C20	2.1 (9)
Re1—P1—C9—C10	−62.3 (4)	C18—C19—C20—C15	−1.3 (9)
C15—P1—C9—C14	−37.4 (4)	C16—C15—C20—C19	−0.3 (8)
C8—P1—C9—C14	−150.6 (4)	P1—C15—C20—C19	178.4 (4)
Re1—P1—C9—C14	115.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···Br1^i	0.98	2.66	3.490 (5)	143
C4—H4···Br1^ii	0.93	2.80	3.552 (5)	139

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

Bromidotricarbonyl[diphenyl(pyridin-2-yl)phosphane-κP](piperidine-κN)rhenium(I) (II)

Crystal data

[ReBr(C5H11N)(C17H14NP)(CO)3]·[+solvent]	Z = 2
Mr = 698.55	F(000) = 676.0
Triclinic, P1	Dx = 1.778 Mg m^−3
a = 9.1384 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8348 (18) Å	Cell parameters from 4721 reflections
c = 15.671 (3) Å	θ = 2.4–22.8°
α = 82.956 (2)°	µ = 6.28 mm^−1
β = 82.047 (2)°	T = 150 K
γ = 69.765 (2)°	Stick, orange
V = 1304.5 (4) Å^3	0.07 × 0.04 × 0.03 mm

Data collection

Bruker SMART CCD area detector diffractometer	4493 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.042
phi and ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: numerical (SADABS; Bruker, 2012)	h = −11→11
Tmin = 0.560, Tmax = 0.858	k = −12→12
10214 measured reflections	l = −19→19
5113 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.082	w = 1/[σ^2(Fo^2) + 9.4699P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max = 0.001
5113 reflections	Δρmax = 1.96 e Å^−3
303 parameters	Δρmin = −1.79 e Å^−3
1 restraint	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00125 (18)

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
Re1	0.83162 (3)	0.70525 (3)	0.70289 (2)	0.01774 (10)
Br1	0.80946 (9)	0.74617 (8)	0.86842 (5)	0.03004 (19)
P1	0.7341 (2)	0.49823 (19)	0.75160 (12)	0.0202 (4)
O1	0.8277 (7)	0.6670 (7)	0.5117 (4)	0.0422 (15)
O3	1.1681 (6)	0.4948 (6)	0.6944 (4)	0.0390 (14)
C1	0.8293 (9)	0.6804 (8)	0.5867 (5)	0.0311 (18)
C3	1.0438 (9)	0.5701 (8)	0.6993 (5)	0.0262 (17)
O2	0.9776 (6)	0.9453 (6)	0.6454 (4)	0.0403 (14)
C2	0.9177 (8)	0.8584 (8)	0.6688 (5)	0.0272 (17)
N1	0.4375 (7)	0.6604 (7)	0.8008 (5)	0.0404 (18)
C10	0.5477 (8)	0.5329 (8)	0.8209 (5)	0.0258 (16)
C12	0.8652 (8)	0.3427 (7)	0.8099 (4)	0.0212 (15)
C4	0.7011 (8)	0.4161 (7)	0.6619 (5)	0.0226 (15)
C13	0.8598 (9)	0.2025 (8)	0.8069 (5)	0.0294 (17)
H13	0.7924	0.1883	0.7722	0.035*
C5	0.5513 (8)	0.4262 (8)	0.6451 (5)	0.0271 (17)
H5	0.4635	0.4741	0.6812	0.032*
C6	0.8295 (9)	0.3428 (9)	0.6070 (5)	0.0329 (19)
H6	0.9298	0.3356	0.6175	0.039*
C14	0.9678 (8)	0.3586 (8)	0.8629 (5)	0.0288 (17)
H14	0.9738	0.4502	0.8667	0.035*
C15	0.9527 (9)	0.0861 (8)	0.8545 (5)	0.035 (2)
H15	0.9469	−0.0058	0.8516	0.042*
C11	0.5179 (9)	0.4359 (9)	0.8863 (5)	0.037 (2)
H11	0.5958	0.3487	0.9002	0.044*
C7	0.8101 (10)	0.2809 (9)	0.5372 (5)	0.038 (2)
H7	0.8971	0.2322	0.5009	0.045*
C8	0.5355 (10)	0.3635 (9)	0.5731 (5)	0.038 (2)
H8	0.4361	0.3716	0.5607	0.046*
N2	0.5893 (6)	0.8705 (7)	0.7094 (4)	0.0267 (14)
C20	1.0531 (8)	0.1025 (8)	0.9058 (5)	0.0312 (19)
H20	1.1158	0.0226	0.9375	0.037*
C22	0.5748 (8)	1.0155 (7)	0.7304 (5)	0.0265 (17)
H22A	0.6209	1.0630	0.6815	0.032*
H22B	0.6333	1.0066	0.7791	0.032*
C21	1.0610 (9)	0.2390 (9)	0.9101 (5)	0.0330 (19)
H21	1.1293	0.2509	0.9451	0.040*
C16	0.6639 (11)	0.2905 (10)	0.5211 (6)	0.042 (2)
H16	0.6518	0.2470	0.4743	0.050*
C18	0.2572 (9)	0.5974 (9)	0.9089 (5)	0.038 (2)
H18	0.1558	0.6203	0.9366	0.046*
C17	0.2958 (9)	0.6904 (10)	0.8455 (7)	0.052 (3)
H17	0.2198	0.7794	0.8325	0.063*
C23	0.4992 (9)	0.8828 (9)	0.6357 (6)	0.038 (2)
H23A	0.5059	0.7862	0.6237	0.045*
H23B	0.5463	0.9251	0.5848	0.045*
C19	0.3699 (10)	0.4708 (10)	0.9308 (6)	0.046 (2)
H19	0.3477	0.4074	0.9756	0.056*
C24	0.4037 (9)	1.1105 (9)	0.7526 (6)	0.037 (2)
H24A	0.3600	1.0682	0.8047	0.045*
H24B	0.3999	1.2067	0.7637	0.045*
C25	0.3279 (9)	0.9750 (9)	0.6520 (6)	0.043 (2)
H25A	0.2777	0.9872	0.5996	0.052*
H25B	0.2763	0.9245	0.6966	0.052*
C27	0.3068 (9)	1.1232 (9)	0.6799 (6)	0.042 (2)
H3A	0.3377	1.1818	0.6312	0.051*
H3B	0.1971	1.1717	0.6986	0.051*
H2N	0.567 (8)	0.828 (5)	0.755 (2)	0.08 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Re1	0.01153 (15)	0.01837 (15)	0.02204 (17)	−0.00440 (10)	−0.00090 (10)	0.00044 (10)
Br1	0.0329 (4)	0.0300 (4)	0.0260 (4)	−0.0077 (3)	−0.0048 (3)	−0.0040 (3)
P1	0.0141 (9)	0.0199 (9)	0.0252 (10)	−0.0052 (7)	−0.0009 (7)	0.0008 (8)
O1	0.042 (4)	0.057 (4)	0.028 (3)	−0.018 (3)	−0.009 (3)	0.004 (3)
O3	0.013 (3)	0.045 (3)	0.051 (4)	−0.001 (3)	0.000 (2)	−0.005 (3)
C1	0.023 (4)	0.034 (4)	0.033 (5)	−0.009 (3)	0.003 (3)	0.001 (4)
C3	0.031 (4)	0.025 (4)	0.025 (4)	−0.012 (4)	−0.003 (3)	−0.002 (3)
O2	0.031 (3)	0.035 (3)	0.061 (4)	−0.022 (3)	0.001 (3)	−0.001 (3)
C2	0.023 (4)	0.024 (4)	0.032 (4)	−0.005 (3)	0.000 (3)	−0.004 (3)
N1	0.018 (3)	0.031 (4)	0.060 (5)	−0.002 (3)	0.013 (3)	0.009 (3)
C10	0.018 (4)	0.028 (4)	0.030 (4)	−0.008 (3)	0.002 (3)	−0.006 (3)
C12	0.017 (3)	0.021 (4)	0.023 (4)	−0.005 (3)	0.002 (3)	0.001 (3)
C4	0.019 (4)	0.021 (4)	0.028 (4)	−0.006 (3)	−0.005 (3)	0.002 (3)
C13	0.027 (4)	0.026 (4)	0.032 (4)	−0.006 (3)	−0.002 (3)	−0.001 (3)
C5	0.023 (4)	0.025 (4)	0.032 (4)	−0.008 (3)	−0.006 (3)	0.003 (3)
C6	0.032 (4)	0.047 (5)	0.023 (4)	−0.016 (4)	0.003 (3)	−0.011 (4)
C14	0.026 (4)	0.031 (4)	0.025 (4)	−0.005 (3)	0.001 (3)	−0.005 (3)
C15	0.030 (4)	0.014 (4)	0.050 (5)	0.001 (3)	0.002 (4)	0.004 (3)
C11	0.026 (4)	0.038 (5)	0.040 (5)	−0.007 (4)	0.006 (4)	0.002 (4)
C7	0.042 (5)	0.039 (5)	0.032 (5)	−0.012 (4)	0.002 (4)	−0.013 (4)
C8	0.037 (5)	0.048 (5)	0.039 (5)	−0.025 (4)	−0.018 (4)	0.010 (4)
N2	0.011 (3)	0.028 (3)	0.039 (4)	−0.008 (3)	−0.002 (3)	0.007 (3)
C20	0.021 (4)	0.028 (4)	0.029 (4)	0.006 (3)	0.002 (3)	0.005 (3)
C22	0.024 (4)	0.020 (4)	0.036 (4)	−0.007 (3)	−0.006 (3)	−0.002 (3)
C21	0.027 (4)	0.040 (5)	0.026 (4)	−0.002 (4)	−0.005 (3)	−0.001 (4)
C16	0.058 (6)	0.048 (5)	0.031 (5)	−0.029 (5)	−0.021 (4)	0.000 (4)
C18	0.024 (4)	0.046 (5)	0.043 (5)	−0.014 (4)	0.014 (4)	−0.012 (4)
C17	0.021 (4)	0.039 (5)	0.076 (7)	0.005 (4)	0.019 (4)	−0.001 (5)
C23	0.022 (4)	0.040 (5)	0.051 (6)	−0.004 (4)	−0.014 (4)	−0.010 (4)
C19	0.033 (5)	0.055 (6)	0.042 (5)	−0.014 (4)	0.013 (4)	0.006 (4)
C24	0.022 (4)	0.032 (4)	0.048 (5)	0.003 (3)	−0.001 (4)	−0.003 (4)
C25	0.032 (5)	0.035 (5)	0.063 (6)	−0.007 (4)	−0.021 (4)	0.004 (4)
C27	0.023 (4)	0.034 (5)	0.061 (6)	0.000 (4)	−0.008 (4)	0.003 (4)

Geometric parameters (Å, º)

Re1—C1	1.870 (8)	C7—C16	1.363 (11)
Re1—C2	1.918 (7)	C7—H7	0.9300
Re1—C3	1.932 (8)	C8—C16	1.361 (12)
Re1—N2	2.246 (6)	C8—H8	0.9300
Re1—P1	2.4915 (18)	N2—C22	1.460 (9)
Re1—Br1	2.6430 (9)	N2—C23	1.479 (10)
P1—C4	1.812 (7)	N2—H2N	0.8200 (10)
P1—C12	1.817 (7)	C20—C21	1.379 (11)
P1—C10	1.837 (7)	C20—H20	0.9300
O1—C1	1.202 (9)	C22—C24	1.536 (10)
O3—C3	1.120 (8)	C22—H22A	0.9700
O2—C2	1.164 (8)	C22—H22B	0.9700
N1—C17	1.338 (9)	C21—H21	0.9300
N1—C10	1.343 (9)	C16—H16	0.9300
C10—C11	1.377 (10)	C18—C19	1.354 (11)
C12—C14	1.394 (10)	C18—C17	1.361 (12)
C12—C13	1.404 (10)	C18—H18	0.9300
C4—C6	1.387 (10)	C17—H17	0.9300
C4—C5	1.398 (9)	C23—C25	1.517 (10)
C13—C15	1.371 (10)	C23—H23A	0.9700
C13—H13	0.9300	C23—H23B	0.9700
C5—C8	1.396 (11)	C19—H19	0.9300
C5—H5	0.9300	C24—C27	1.505 (12)
C6—C7	1.375 (10)	C24—H24A	0.9700
C6—H6	0.9300	C24—H24B	0.9700
C14—C21	1.387 (10)	C25—C27	1.514 (11)
C14—H14	0.9300	C25—H25A	0.9700
C15—C20	1.362 (11)	C25—H25B	0.9700
C15—H15	0.9300	C27—H3A	0.9700
C11—C19	1.382 (10)	C27—H3B	0.9700
C11—H11	0.9300
C1—Re1—C2	90.1 (3)	C16—C8—H8	119.6
C1—Re1—C3	89.4 (3)	C5—C8—H8	119.6
C2—Re1—C3	88.0 (3)	C22—N2—C23	109.6 (6)
C1—Re1—N2	92.3 (3)	C22—N2—Re1	116.4 (4)
C2—Re1—N2	89.6 (3)	C23—N2—Re1	116.1 (5)
C3—Re1—N2	177.1 (3)	C22—N2—H2N	106 (4)
C1—Re1—P1	91.6 (2)	C23—N2—H2N	118 (5)
C2—Re1—P1	176.6 (2)	Re1—N2—H2N	89 (5)
C3—Re1—P1	89.0 (2)	C15—C20—C21	119.3 (7)
N2—Re1—P1	93.28 (16)	C15—C20—H20	120.4
C1—Re1—Br1	175.3 (2)	C21—C20—H20	120.4
C2—Re1—Br1	92.1 (2)	N2—C22—C24	112.6 (6)
C3—Re1—Br1	94.9 (2)	N2—C22—H22A	109.1
N2—Re1—Br1	83.53 (17)	C24—C22—H22A	109.1
P1—Re1—Br1	86.44 (5)	N2—C22—H22B	109.1
C4—P1—C12	102.0 (3)	C24—C22—H22B	109.1
C4—P1—C10	102.6 (3)	H22A—C22—H22B	107.8
C12—P1—C10	102.6 (3)	C20—C21—C14	120.6 (8)
C4—P1—Re1	112.4 (2)	C20—C21—H21	119.7
C12—P1—Re1	116.4 (2)	C14—C21—H21	119.7
C10—P1—Re1	118.7 (2)	C8—C16—C7	120.3 (8)
O1—C1—Re1	178.8 (7)	C8—C16—H16	119.8
O3—C3—Re1	177.3 (7)	C7—C16—H16	119.8
O2—C2—Re1	175.9 (6)	C19—C18—C17	118.4 (7)
C17—N1—C10	118.0 (7)	C19—C18—H18	120.8
N1—C10—C11	121.6 (7)	C17—C18—H18	120.8
N1—C10—P1	114.4 (5)	N1—C17—C18	123.4 (8)
C11—C10—P1	124.0 (6)	N1—C17—H17	118.3
C14—C12—C13	117.5 (7)	C18—C17—H17	118.3
C14—C12—P1	121.7 (5)	N2—C23—C25	113.0 (7)
C13—C12—P1	120.7 (5)	N2—C23—H23A	109.0
C6—C4—C5	118.9 (7)	C25—C23—H23A	109.0
C6—C4—P1	118.6 (5)	N2—C23—H23B	109.0
C5—C4—P1	122.5 (6)	C25—C23—H23B	109.0
C15—C13—C12	120.9 (7)	H23A—C23—H23B	107.8
C15—C13—H13	119.6	C18—C19—C11	119.9 (8)
C12—C13—H13	119.6	C18—C19—H19	120.0
C8—C5—C4	119.0 (7)	C11—C19—H19	120.0
C8—C5—H5	120.5	C27—C24—C22	111.0 (7)
C4—C5—H5	120.5	C27—C24—H24A	109.4
C7—C6—C4	120.7 (7)	C22—C24—H24A	109.4
C7—C6—H6	119.7	C27—C24—H24B	109.4
C4—C6—H6	119.7	C22—C24—H24B	109.4
C21—C14—C12	120.5 (7)	H24A—C24—H24B	108.0
C21—C14—H14	119.7	C27—C25—C23	112.4 (7)
C12—C14—H14	119.7	C27—C25—H25A	109.1
C20—C15—C13	121.2 (8)	C23—C25—H25A	109.1
C20—C15—H15	119.4	C27—C25—H25B	109.1
C13—C15—H15	119.4	C23—C25—H25B	109.1
C10—C11—C19	118.6 (8)	H25A—C25—H25B	107.8
C10—C11—H11	120.7	C24—C27—C25	111.1 (7)
C19—C11—H11	120.7	C24—C27—H3A	109.4
C16—C7—C6	120.3 (8)	C25—C27—H3A	109.4
C16—C7—H7	119.8	C24—C27—H3B	109.4
C6—C7—H7	119.8	C25—C27—H3B	109.4
C16—C8—C5	120.8 (7)	H3A—C27—H3B	108.0
C17—N1—C10—C11	−0.9 (13)	P1—C4—C6—C7	−178.9 (6)
C17—N1—C10—P1	176.7 (7)	C13—C12—C14—C21	0.4 (10)
C4—P1—C10—N1	−86.6 (6)	P1—C12—C14—C21	176.7 (5)
C12—P1—C10—N1	167.9 (6)	C12—C13—C15—C20	−0.2 (12)
Re1—P1—C10—N1	37.9 (7)	N1—C10—C11—C19	1.1 (13)
C4—P1—C10—C11	90.9 (7)	P1—C10—C11—C19	−176.3 (7)
C12—P1—C10—C11	−14.6 (8)	C4—C6—C7—C16	−0.1 (13)
Re1—P1—C10—C11	−144.5 (6)	C4—C5—C8—C16	1.5 (11)
C4—P1—C12—C14	155.1 (6)	C13—C15—C20—C21	0.3 (12)
C10—P1—C12—C14	−98.9 (6)	C23—N2—C22—C24	58.2 (8)
Re1—P1—C12—C14	32.4 (7)	Re1—N2—C22—C24	−167.6 (5)
C4—P1—C12—C13	−28.7 (6)	C15—C20—C21—C14	0.0 (11)
C10—P1—C12—C13	77.3 (6)	C12—C14—C21—C20	−0.3 (11)
Re1—P1—C12—C13	−151.4 (5)	C5—C8—C16—C7	−1.7 (13)
C12—P1—C4—C6	−58.3 (6)	C6—C7—C16—C8	1.0 (13)
C10—P1—C4—C6	−164.3 (6)	C10—N1—C17—C18	−1.2 (15)
Re1—P1—C4—C6	67.1 (6)	C19—C18—C17—N1	3.1 (15)
C12—P1—C4—C5	123.0 (6)	C22—N2—C23—C25	−56.3 (8)
C10—P1—C4—C5	17.0 (7)	Re1—N2—C23—C25	169.3 (5)
Re1—P1—C4—C5	−111.6 (6)	C17—C18—C19—C11	−2.9 (14)
C14—C12—C13—C15	−0.1 (11)	C10—C11—C19—C18	0.8 (14)
P1—C12—C13—C15	−176.5 (6)	N2—C22—C24—C27	−56.7 (9)
C6—C4—C5—C8	−0.5 (11)	N2—C23—C25—C27	53.0 (10)
P1—C4—C5—C8	178.2 (6)	C22—C24—C27—C25	51.0 (9)
C5—C4—C6—C7	−0.2 (11)	C23—C25—C27—C24	−49.9 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···N1	0.82	2.34	2.992 (9)	138
C14—H14···Br1	0.93	2.78	3.586 (8)	146
C22—H22B···Br1	0.97	2.83	3.499 (7)	127