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Acta Cryst. (2023). E79, 982-987
https://doi.org/10.1107/S2056989023008514
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Unusual reaction of (E)-2-[(benzo[d]thia­zol-2-yl­imino)­meth­yl]-5-(di­ethyl­amino)­phenol with tri­phenyl­borane: crystal structures and optical properties

H. Le Thi Hong, T. Le Phuong, T. Van Pham, H. Minh Thi Nguyen and L. Van Meervelt
The mol­ecular and crystal structure of (E)-2-[(benzo[d]thia­zol-2-yl­imino)­meth­yl]-5-(di­ethyl­amino)­phenol and its reaction product with tri­phenyl­borane are described. In compound Et2N-Bz, one of the ethyl groups and the benzo­thia­zole ring are disordered over two sets of atomic sites with major occupancy components of 0.822 (5) and 0.843 (2), respectively.
Keywords: crystal structure; benzo­thia­zole; boranils; fluorescence; aggregation-induced emission.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989023008514/pk2698sup1.cif
Contains datablocks Et2N-Bz, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989023008514/pk2698Et2N-Bzsup2.hkl
Contains datablock Et2N-Bz

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989023008514/pk2698Isup3.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989023008514/pk2698Et2N-Bzsup4.cml
Supplementary material

png

Portable Network Graphics (PNG) image https://doi.org/10.1107/S2056989023008514/pk2698sup5.png
Fig. S1

CCDC references: 2297768; 2297767

checkCIF report

Key indicators

Structure: Et2N-Bz
  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.053
  • wR factor = 0.138
  • Data-to-parameter ratio = 14.8
Structure: I
  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.069
  • wR factor = 0.196
  • Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Datablock: Et2N-Bz




Alert level C
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........        S1C Check
                    S1C         C2
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........       S1BD Check
                    S1BD        C2
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........        N3C Check
                    N3C         C2
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........       N3BD Check
                    N3BD        C2
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........       S1BD Check
                    S1BD        C4
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........        N3C Check
                    N3C         C4
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........        S1C Check
                    S1C         C9
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........       N3BD Check
                    N3BD        C9
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........       C20A Check
                    C20A        H20A
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........       C20A Check
                    C20A        H20B
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........      C20BB Check
                    C20BB       H20C
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........      C20BB Check
                    C20BB       H20D
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........       C20A Check
                    C20A        C21
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........       C21A Check
                    C21A        H21A
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........       C21A Check
                    C21A        H21B
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........       C21A Check
                    C21A        H21C
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........      C20BB Check
                    C20BB       C21B
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........      C21BB Check
                    C21BB       H21D
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........      C21BB Check
                    C21BB       H21E
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........      C21BB Check
                    C21BB       H21F
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C21BB Check
                    C21BB       C20BB       N19
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........       C21A Check
                    C21A        C20A        H20A
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      H20AA Check
                    H20AA       C20A        H20B
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........       C21A Check
                    C21A        C20A        H20B
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C21BB Check
                    C21BB       C20BB       H20C
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C21BB Check
                    C21BB       C20BB       H20D
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      H20CB Check
                    H20CB       C20BB       H20D
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........       C20A Check
                    C20A        C21A        H21A
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........       C20A Check
                    C20A        C21A        H21B
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      H21AA Check
                    H21AA       C21A        H21B
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      H21BA Check
                    H21BA       C21A        H21C
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........       C20A Check
                    C20A        C21A        H21C
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      H21AA Check
                    H21AA       C21A        H21C
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C20BB Check
                    C20BB       C21BB       H21D
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      H21DB Check
                    H21DB       C21BB       H21E
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C20BB Check
                    C20BB       C21BB       H21E
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C20BB Check
                    C20BB       C21BB       H21F
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      H21DB Check
                    H21DB       C21BB       H21F
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      H21EB Check
                    H21EB       C21BB       H21F
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........        N3C Check
                    N3C         C2          S1
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........       N3BD Check
                    N3BD        C2          S1B
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........        N3C Check
                    N3C         C2          N10
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........       N3BD Check
                    N3BD        C2          N10
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........        N3C Check
                    C2          N3C         C4
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........       N3BD Check
                    C2          N3BD        C9
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........       S1BD Check
                    C4          S1BD        C2
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........        S1C Check
                    C9          S1C         C2
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........       C20A Check
                    N19         C20A        H20A
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........       C20A Check
                    N19         C20A        H20B
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C20BB Check
                    N19         C20BB       H20C
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C20BB Check
                    N19         C20BB       H20D
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........       C20A Check
                    N19         C20A        C21
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........        N3C Check
                    C4          N3C         C2          N10
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........        N3C Check
                    N3C         C4          C9          S1C
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........        S1C Check
                    C5          C4          C9          S1C
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........       S1BD Check
                    C4          S1BD        C2          N10
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........       N3BD Check
                    C9          N3BD        C2          N10
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........       N3BD Check
                    C5          C4          C9          N3BD
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........       S1BD Check
                    S1BD        C4          C9          N3BD
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........       S1BD Check
                    C4          S1BD        C2          N3BD
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........        N3C Check
                    C4          N3C         C2          S1C
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........        S1C Check
                    C9          S1C         C2          N10
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........        S1C Check
                    C7          C8          C9          S1C
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........       N3BD Check
                    C7          C8          C9          N3BD
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........       C20A Check
                    C14         C15         N19         C20A
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........        S1C Check
                    C9          S1C         C2          N3C
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........      C20BB Check
                    C14         C15         N19         C20BB
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........       C20A Check
                    C16         C15         N19         C20A
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........      C20BB Check
                    C16         C15         N19         C20BB
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........       N3BD Check
                    C9          N3BD        C2          S1BD
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........        N3C Check
                    C2          N3C         C4          C5
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........       S1BD Check
                    C2          S1BD        C4          C5
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........       S1BD Check
                    C2          S1BD        C4          C9
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........        N3C Check
                    C2          N3C         C4          C9
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........       S1BD Check
                    S1BD        C4          C5          C6
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........        N3C Check
                    N3C         C4          C5          C6
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........        S1C Check
                    C2          S1C         C9          C4
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........       N3BD Check
                    C2          N3BD        C9          C4
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........        N3C Check
                    N3C         C4          C9          C8
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........       S1BD Check
                    S1BD        C4          C9          C8
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........       N3BD Check
                    C2          N3BD        C9          C8
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........        S1C Check
                    C2          S1C         C9          C8
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........        S1C Check
                    S1C         C2          N10         C11
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........       N3BD Check
                    N3BD        C2          N10         C11
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........        N3C Check
                    N3C         C2          N10         C11
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........       S1BD Check
                    S1BD        C2          N10         C11
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........       C20A Check
                    C20A        N19         C22         C23
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........      C20BB Check
                    C20BB       N19         C22         C23
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........       C20A Check
                    C15         N19         C20A        C21A
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........      C20BB Check
                    C15         N19         C20BB       C21BB
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........      C20BB Check
                    C22         N19         C20BB       C21BB
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........       C20A Check
                    C22         N19         C20A        C21A
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.776 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          7 Report


Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         12 Note
PLAT073_ALERT_1_G H-atoms ref, but _hydrogen_treatment Reported as     constr Check
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          4 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          5 Report
PLAT191_ALERT_3_G A Non-default SADI Restraint Value has been used     0.0100 Report
PLAT191_ALERT_3_G A Non-default SADI Restraint Value has been used     0.0100 Report
PLAT191_ALERT_3_G A Non-default SADI Restraint Value has been used     0.0100 Report
PLAT230_ALERT_2_G Hirshfeld Test Diff for    S1       --C9       .        6.7 s.u.
PLAT230_ALERT_2_G Hirshfeld Test Diff for    S1B      --C4       .        7.8 s.u.
PLAT230_ALERT_2_G Hirshfeld Test Diff for    N19      --C20B     .        6.7 s.u.
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        17% Note
PLAT410_ALERT_2_G Short Intra H...H Contact  H16      ..H20B     .       2.09 Ang.
                                                      x,y,z  =      1_555 Check
PLAT412_ALERT_2_G Short Intra XH3 .. XHn     H23C     ..H20C     .       2.04 Ang.
                                                      x,y,z  =      1_555 Check
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters         12 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          5 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          7 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
   0 ALERT level B = A potentially serious problem, consider carefully
  94 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  18 ALERT level G = General information/check it is not something unexpected

  93 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   8 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





Datablock: I



Alert level C
PLAT220_ALERT_2_C NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range        3.6 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1       --C22      .        6.7 s.u.
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         C3 Check
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         C4 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C20 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C22 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00479 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     14.550 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.245 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          7 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report


Alert level G
PLAT045_ALERT_1_G Calculated and Reported Z Differ by a Factor ...          2 Check
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          6 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        4.0 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info
PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by          2 Check


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

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

Data collection: CrysAlis PRO 1.171.42.73a (Rigaku OD, 2022) for Et2N-Bz; CrysAlis PRO 1.171.40.25a (Rigaku OD, 2022) for (I). Cell refinement: CrysAlis PRO 1.171.42.73a (Rigaku OD, 2022) for Et2N-Bz; CrysAlis PRO 1.171.40.25a (Rigaku OD, 2022) for (I). Data reduction: CrysAlis PRO 1.171.42.73a (Rigaku OD, 2022) for Et2N-Bz; CrysAlis PRO 1.171.40.25a (Rigaku OD, 2022) for (I). For both structures, program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016/4 (Sheldrick, 2015b); molecular graphics: Olex2 1.3 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 1.3 (Dolomanov et al., 2009).

(E)-2-[(Benzo[d]thiazol-2-ylimino)methyl]-5-(diethylamino)phenol (Et2N-Bz) top
Crystal data top
C18H19N3OSF(000) = 688
Mr = 325.42Dx = 1.309 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 7.2881 (2) ÅCell parameters from 10518 reflections
b = 22.0453 (8) Åθ = 2.9–28.1°
c = 10.2761 (3) ŵ = 0.20 mm−1
β = 90.280 (3)°T = 294 K
V = 1651.02 (9) Å3Plate, orange
Z = 40.45 × 0.3 × 0.05 mm
Data collection top
SuperNova, Single source at offset/far, Eos
diffractometer		3366 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source2650 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.039
Detector resolution: 15.9631 pixels mm-1θmax = 26.4°, θmin = 2.7°
ω scansh = −9→9
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2022)		k = −27→27
Tmin = 0.395, Tmax = 1.000l = −12→12
33381 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H-atom parameters constrained
wR(F2) = 0.138 w = 1/[σ2(Fo2) + (0.0472P)2 + 1.010P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
3366 reflectionsΔρmax = 0.40 e Å−3
227 parametersΔρmin = −0.27 e Å−3
5 restraints
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.22145 (11)0.35862 (4)0.49674 (8)0.0589 (3)0.843 (2)
N30.5480 (4)0.33979 (12)0.4072 (3)0.0509 (6)0.843 (2)
S1B0.6141 (8)0.3376 (3)0.3866 (6)0.0589 (3)0.157 (2)
N3B0.2914 (14)0.3507 (6)0.4767 (13)0.0509 (6)0.157 (2)
C20.4561 (3)0.37408 (9)0.48618 (19)0.0476 (5)
C40.4325 (3)0.29811 (10)0.3439 (2)0.0555 (6)
C50.4808 (4)0.25480 (12)0.2522 (3)0.0741 (8)
H50.6018600.2511920.2251750.089*
C60.3495 (6)0.21786 (14)0.2026 (3)0.0910 (10)
H60.3819880.1888900.1411230.109*
C70.1721 (6)0.22200 (14)0.2403 (3)0.0915 (10)
H70.0860040.1957630.2040730.110*
C80.1154 (4)0.26439 (14)0.3316 (3)0.0819 (8)
H8−0.0065680.2671260.3572110.098*
C90.2508 (4)0.30300 (11)0.3837 (2)0.0599 (6)
N100.5154 (2)0.42027 (8)0.56646 (16)0.0485 (4)
C110.6886 (3)0.43504 (9)0.57170 (19)0.0466 (5)
H110.7715600.4146360.5189840.056*
C120.7534 (3)0.48131 (9)0.65551 (18)0.0426 (5)
C130.6334 (3)0.51562 (9)0.7349 (2)0.0441 (5)
C140.6985 (3)0.55958 (10)0.8176 (2)0.0487 (5)
H140.6159340.5812850.8682380.058*
C150.8867 (3)0.57262 (10)0.8276 (2)0.0507 (5)
C161.0081 (3)0.53789 (11)0.7490 (2)0.0566 (6)
H161.1338040.5447470.7540320.068*
C170.9420 (3)0.49499 (11)0.6671 (2)0.0519 (5)
H171.0246810.4735320.6160780.062*
O180.45128 (19)0.50579 (8)0.73184 (17)0.0593 (4)
H180.4263 (9)0.4748 (14)0.678 (3)0.089*
N190.9503 (3)0.61697 (10)0.9084 (2)0.0656 (6)
C201.1470 (4)0.63271 (18)0.9180 (4)0.0757 (11)0.822 (5)
H20A1.1597410.6743930.9468690.091*0.822 (5)
H20B1.2030610.6292110.8329330.091*0.822 (5)
C20B1.1347 (19)0.6014 (8)0.9781 (17)0.0757 (11)0.178 (5)
H20C1.1275500.6069731.0715690.091*0.178 (5)
H20D1.1756300.5605080.9588300.091*0.178 (5)
C211.2439 (5)0.5911 (2)1.0127 (4)0.1063 (16)0.822 (5)
H21A1.2364290.5501000.9817550.159*0.822 (5)
H21B1.1866080.5939611.0963480.159*0.822 (5)
H21C1.3703790.6028741.0200400.159*0.822 (5)
C21B1.253 (2)0.6487 (10)0.9142 (18)0.1063 (16)0.178 (5)
H21D1.2604910.6406530.8225780.159*0.178 (5)
H21E1.3740320.6475800.9516880.159*0.178 (5)
H21F1.2004600.6881370.9276490.159*0.178 (5)
C220.8250 (3)0.65065 (12)0.9929 (2)0.0645 (7)
H22A0.7144480.6601610.9440810.077*
H22B0.8824880.6886931.0173380.077*
C230.7730 (4)0.61722 (15)1.1136 (3)0.0833 (9)
H23A0.7145270.5797061.0903750.125*
H23B0.6899850.6415231.1636620.125*
H23C0.8811840.6089421.1642250.125*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0620 (5)0.0571 (5)0.0577 (5)−0.0060 (4)0.0067 (4)−0.0146 (3)
N30.0554 (16)0.0500 (14)0.0473 (14)0.0042 (13)−0.0004 (12)0.0006 (10)
S1B0.0620 (5)0.0571 (5)0.0577 (5)−0.0060 (4)0.0067 (4)−0.0146 (3)
N3B0.0554 (16)0.0500 (14)0.0473 (14)0.0042 (13)−0.0004 (12)0.0006 (10)
C20.0601 (13)0.0421 (11)0.0404 (10)0.0015 (9)−0.0025 (9)0.0023 (9)
C40.0757 (16)0.0406 (12)0.0501 (12)0.0028 (11)−0.0060 (11)0.0037 (10)
C50.100 (2)0.0544 (15)0.0685 (16)0.0111 (14)0.0075 (15)−0.0057 (13)
C60.144 (3)0.0584 (17)0.0705 (18)−0.0063 (19)0.009 (2)−0.0179 (14)
C70.128 (3)0.073 (2)0.0736 (19)−0.035 (2)−0.0106 (19)−0.0159 (16)
C80.0814 (19)0.088 (2)0.0765 (18)−0.0213 (16)0.0033 (15)0.0036 (16)
C90.0785 (17)0.0535 (14)0.0478 (12)−0.0060 (12)−0.0003 (11)0.0006 (10)
N100.0563 (11)0.0436 (10)0.0455 (9)−0.0018 (8)−0.0026 (8)−0.0019 (8)
C110.0555 (12)0.0435 (11)0.0409 (10)0.0086 (9)0.0009 (9)0.0028 (9)
C120.0442 (11)0.0435 (11)0.0402 (10)0.0050 (8)−0.0002 (8)0.0013 (8)
C130.0372 (10)0.0465 (11)0.0484 (11)0.0013 (8)0.0006 (8)0.0006 (9)
C140.0408 (11)0.0538 (13)0.0516 (12)0.0051 (9)0.0031 (9)−0.0079 (10)
C150.0432 (11)0.0589 (13)0.0499 (12)0.0006 (10)−0.0027 (9)−0.0063 (10)
C160.0357 (10)0.0760 (16)0.0579 (13)0.0012 (10)0.0019 (9)−0.0095 (12)
C170.0423 (11)0.0642 (14)0.0492 (11)0.0090 (10)0.0065 (9)−0.0046 (10)
O180.0365 (8)0.0677 (11)0.0737 (11)−0.0037 (7)0.0048 (7)−0.0206 (9)
N190.0486 (11)0.0791 (15)0.0689 (13)−0.0058 (10)−0.0028 (9)−0.0229 (11)
C200.0567 (18)0.090 (3)0.081 (3)−0.0225 (19)0.0038 (18)−0.022 (2)
C20B0.0567 (18)0.090 (3)0.081 (3)−0.0225 (19)0.0038 (18)−0.022 (2)
C210.059 (2)0.181 (5)0.079 (2)0.019 (3)−0.0123 (19)−0.016 (3)
C21B0.059 (2)0.181 (5)0.079 (2)0.019 (3)−0.0123 (19)−0.016 (3)
C220.0664 (15)0.0600 (15)0.0670 (15)−0.0030 (12)−0.0060 (12)−0.0161 (12)
C230.085 (2)0.099 (2)0.0665 (17)0.0015 (17)−0.0003 (14)−0.0042 (16)
Geometric parameters (Å, º) top
S1c—C21.748 (2)C7—C81.389 (4)
S1Bd—C21.741 (5)C8—H80.9300
N3c—C21.298 (3)C8—C91.407 (4)
N3Bd—C21.310 (9)N10—C111.304 (3)
S1Bd—C41.642 (6)C11—H110.9300
N3c—C41.403 (3)C11—C121.415 (3)
S1c—C91.703 (2)C12—C131.418 (3)
N3Bd—C91.450 (9)C12—C171.412 (3)
C20a—H20A0.9700C13—C141.372 (3)
C20a—H20B0.9700C13—O181.345 (2)
C20Bb—H20C0.9700C14—H140.9300
C20Bb—H20D0.9700C14—C151.405 (3)
C20a—C211.510 (6)C15—C161.424 (3)
C21a—H21A0.9600C15—N191.363 (3)
C21a—H21B0.9600C16—H160.9300
C21a—H21C0.9600C16—C171.353 (3)
C20Bb—C21B1.508 (17)C17—H170.9300
C21Bb—H21D0.9600O18—H180.90 (3)
C21Bb—H21E0.9600N19—C201.477 (4)
C21Bb—H21F0.9600N19—C20B1.558 (15)
C2—N101.379 (3)N19—C221.465 (3)
C4—C51.388 (3)C22—H22A0.9700
C4—C91.392 (3)C22—H22B0.9700
C5—H50.9300C22—C231.493 (4)
C5—C61.354 (4)C23—H23A0.9600
C6—H60.9300C23—H23B0.9600
C6—C71.355 (5)C23—H23C0.9600
C7—H70.9300
C21Bb—C20Bb—N1998.2 (13)C8—C9—S1127.2 (2)
N10—C2—S1114.26 (15)C8—C9—N3B146.0 (5)
N10—C2—S1B119.1 (3)C9—S1c—C288.38 (12)
C21a—C20a—H20A109.5C11—N10—C2120.64 (19)
H20Aa—C20a—H20B108.1N10—C11—H11119.1
C21a—C20a—H20B109.5N10—C11—C12121.70 (19)
C21Bb—C20Bb—H20C112.1C12—C11—H11119.1
C21Bb—C20Bb—H20D112.1C11—C12—C13121.98 (19)
H20Cb—C20Bb—H20D109.8C17—C12—C11121.86 (19)
C20a—C21a—H21A109.5C17—C12—C13116.15 (18)
C20a—C21a—H21B109.5C14—C13—C12121.39 (18)
H21Aa—C21a—H21B109.5O18—C13—C12120.82 (18)
H21Ba—C21a—H21C109.5O18—C13—C14117.79 (18)
C20a—C21a—H21C109.5C13—C14—H14119.2
H21Aa—C21a—H21C109.5C13—C14—C15121.63 (19)
C20Bb—C21Bb—H21D109.5C15—C14—H14119.2
H21Db—C21Bb—H21E109.5C14—C15—C16117.2 (2)
C20Bb—C21Bb—H21E109.5N19—C15—C14121.4 (2)
C20Bb—C21Bb—H21F109.5N19—C15—C16121.38 (19)
H21Db—C21Bb—H21F109.5C15—C16—H16119.7
H21Eb—C21Bb—H21F109.5C17—C16—C15120.6 (2)
N3c—C2—S1115.66 (19)C17—C16—H16119.7
N3Bd—C2—S1B112.5 (5)C12—C17—H17118.5
N3c—C2—N10130.1 (2)C16—C17—C12123.0 (2)
N3Bd—C2—N10128.3 (5)C16—C17—H17118.5
C2—N3c—C4111.2 (3)C13—O18—H18109.5
C2—N3Bd—C9121.2 (8)C15—N19—C20122.4 (2)
C4—S1Bd—C282.4 (3)C15—N19—C20B114.3 (7)
C5—C4—N3127.7 (3)C15—N19—C22120.89 (19)
C5—C4—S1B109.8 (3)C22—N19—C20116.7 (2)
C5—C4—C9119.8 (2)N19—C20a—H20A109.5
C9—C4—N3112.5 (2)N19—C20a—H20B109.5
C9—C4—S1B130.3 (3)N19—C20Bb—H20C112.1
C4—C5—H5120.4N19—C20Bb—H20D112.1
C6—C5—C4119.2 (3)N19—C20a—C21110.6 (3)
C6—C5—H5120.4C22—N19—C20B112.2 (7)
C5—C6—H6119.2N19—C22—H22A108.8
C5—C6—C7121.7 (3)N19—C22—H22B108.8
C7—C6—H6119.2N19—C22—C23113.8 (2)
C6—C7—H7119.1H22A—C22—H22B107.7
C6—C7—C8121.8 (3)C23—C22—H22A108.8
C8—C7—H7119.1C23—C22—H22B108.8
C7—C8—H8121.5C22—C23—H23A109.5
C7—C8—C9117.0 (3)C22—C23—H23B109.5
C9—C8—H8121.5C22—C23—H23C109.5
C4—C9—S1112.27 (18)H23A—C23—H23B109.5
C4—C9—N3B93.4 (5)H23A—C23—H23C109.5
C4—C9—C8120.5 (2)H23B—C23—H23C109.5
C4—N3c—C2—N10179.9 (2)S1Bd—C4—C9—C8178.8 (4)
N3c—C4—C9—S1c0.5 (3)C2—N3Bd—C9—C8−178.8 (4)
C5—C4—C9—S1c179.79 (18)C2—S1c—C9—C8−179.8 (2)
C4—S1Bd—C2—N10179.3 (2)S1c—C2—N10—C11177.55 (15)
C9—N3Bd—C2—N10178.2 (6)N3Bd—C2—N10—C11174.4 (9)
C5—C4—C9—N3Bd177.7 (6)N3c—C2—N10—C11−0.6 (4)
S1Bd—C4—C9—N3Bd−3.4 (7)S1Bd—C2—N10—C11−2.6 (4)
C2—N10—C11—C12−178.51 (18)C20a—N19—C22—C23−99.1 (3)
C4—S1Bd—C2—N3Bd1.8 (9)C20Bb—N19—C22—C23−60.2 (7)
C4—N3c—C2—S1c1.7 (3)C9—C4—C5—C60.1 (4)
C9—S1c—C2—N10−179.71 (16)N10—C11—C12—C13−2.3 (3)
C4—C5—C6—C7−0.1 (5)N10—C11—C12—C17176.20 (19)
C5—C4—C9—C80.0 (4)C11—C12—C13—C14178.74 (19)
C5—C6—C7—C80.1 (5)C11—C12—C13—O18−0.9 (3)
C6—C7—C8—C9−0.1 (5)C11—C12—C17—C16−178.2 (2)
C7—C8—C9—S1c−179.8 (2)C12—C13—C14—C150.0 (3)
C7—C8—C9—N3Bd−175.9 (11)C13—C12—C17—C160.4 (3)
C7—C8—C9—C40.0 (4)C13—C14—C15—C16−0.5 (3)
C14—C15—N19—C20a−178.3 (3)C13—C14—C15—N19179.0 (2)
C9—S1c—C2—N3c−1.3 (2)C14—C15—C16—C171.1 (3)
C14—C15—N19—C20Bb142.1 (7)C14—C15—N19—C223.1 (4)
C16—C15—N19—C20a1.3 (4)C15—C16—C17—C12−1.0 (4)
C16—C15—N19—C20Bb−38.4 (8)C15—N19—C20a—C21a−84.6 (4)
C9—N3Bd—C2—S1Bd−4.7 (15)C15—N19—C20Bb—C21Bb114.0 (11)
C2—N3c—C4—C5179.3 (2)C15—N19—C22—C2379.6 (3)
C2—S1Bd—C4—C5−179.7 (2)C16—C15—N19—C22−177.4 (2)
C2—S1Bd—C4—C91.3 (5)C17—C12—C13—C140.1 (3)
C2—N3c—C4—C9−1.4 (3)C17—C12—C13—O18−179.50 (19)
S1Bd—C4—C5—C6−179.0 (3)O18—C13—C14—C15179.6 (2)
N3c—C4—C5—C6179.3 (3)N19—C15—C16—C17−178.5 (2)
C2—S1c—C9—C40.37 (18)C22—N19—C20Bb—C21Bb−103.5 (12)
C2—N3Bd—C9—C44.7 (12)C22—N19—C20a—C21a94.1 (3)
N3c—C4—C9—C8−179.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O18—H18···N100.90 (3)1.79 (3)2.582 (2)147 (1)
C16—H16···O18i0.932.483.312 (3)149
Symmetry code: (i) x+1, y, z.
7-(Diethylamino)-2,2-diphenyl-1,3-dioxa-2-borata-1,2-dihydronaphthalene (I) top
Crystal data top
C23H24BNO2Z = 4
Mr = 362.24F(000) = 760
Triclinic, P1Dx = 1.162 Mg m−3
a = 10.6725 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.8934 (4) ÅCell parameters from 7067 reflections
c = 16.1411 (7) Åθ = 2.9–22.8°
α = 86.207 (3)°µ = 0.07 mm−1
β = 87.553 (4)°T = 293 K
γ = 88.394 (3)°Needle, brown
V = 2041.82 (15) Å30.5 × 0.15 × 0.15 mm
Data collection top
SuperNova, Single source at offset/far, Eos
diffractometer		8340 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source4623 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.046
Detector resolution: 15.9631 pixels mm-1θmax = 26.4°, θmin = 2.5°
ω scansh = −13→13
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2022)		k = −14→14
Tmin = 0.839, Tmax = 1.000l = −20→20
33181 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.069H-atom parameters constrained
wR(F2) = 0.196 w = 1/[σ2(Fo2) + (0.0636P)2 + 0.750P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
8340 reflectionsΔρmax = 0.18 e Å−3
491 parametersΔρmin = −0.18 e Å−3
0 restraints
Special details top

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 (Å2) top
xyzUiso*/Ueq
O10.53603 (19)−0.09682 (14)0.73035 (12)0.0662 (5)
N10.8206 (3)0.1521 (2)0.42080 (15)0.0827 (8)
C10.5824 (3)−0.1290 (2)0.66118 (19)0.0762 (9)
H10.572647−0.2038350.6498760.091*
B10.5754 (3)0.0205 (2)0.75708 (19)0.0552 (8)
O20.59385 (18)0.09724 (13)0.67987 (11)0.0602 (5)
N20.3505 (2)0.6467 (2)0.95420 (14)0.0666 (6)
B20.7059 (3)0.5222 (2)0.66826 (19)0.0524 (7)
O30.65253 (18)0.40191 (14)0.66678 (12)0.0650 (5)
O40.60878 (15)0.59518 (13)0.71133 (10)0.0535 (5)
C240.5782 (3)0.3668 (2)0.72724 (17)0.0596 (7)
H240.5581920.2909860.7309690.072*
C250.5264 (2)0.4334 (2)0.78661 (16)0.0524 (6)
C260.4490 (3)0.3909 (2)0.85421 (18)0.0649 (8)
H260.4363440.3137400.8610570.078*
C270.3929 (3)0.4591 (3)0.90907 (18)0.0678 (8)
H270.3447520.4280830.9537680.081*
C280.4068 (2)0.5784 (2)0.89925 (16)0.0542 (6)
C290.4804 (2)0.6220 (2)0.83050 (15)0.0501 (6)
H290.4879680.6996600.8217330.060*
C300.5411 (2)0.5527 (2)0.77622 (15)0.0465 (6)
C310.8321 (3)0.5120 (2)0.71860 (16)0.0581 (7)
C320.9044 (3)0.4135 (3)0.7290 (2)0.0870 (10)
H320.8747400.3466630.7113730.104*
C331.0206 (5)0.4131 (5)0.7654 (3)0.1164 (16)
H331.0675310.3461840.7715360.140*
C341.0660 (4)0.5099 (6)0.7922 (3)0.1203 (18)
H341.1439840.5092660.8157940.144*
C350.9976 (4)0.6054 (4)0.7842 (2)0.1055 (13)
H351.0276740.6711920.8034190.127*
C360.8826 (3)0.6077 (3)0.7477 (2)0.0795 (9)
H360.8373990.6755850.7424860.095*
C370.7232 (3)0.5703 (2)0.57312 (16)0.0529 (6)
C380.8380 (3)0.5875 (3)0.53268 (19)0.0810 (10)
H380.9105600.5714970.5616500.097*
C390.8491 (4)0.6280 (3)0.4501 (2)0.0946 (11)
H390.9280810.6376330.4244010.114*
C400.7446 (4)0.6536 (3)0.4067 (2)0.0833 (10)
H400.7514500.6814880.3515100.100*
C410.6304 (4)0.6378 (3)0.4449 (2)0.0820 (9)
H410.5583120.6553470.4157340.098*
C420.6199 (3)0.5962 (2)0.52636 (19)0.0695 (8)
H420.5403740.5850470.5507790.083*
C430.2803 (3)0.6019 (3)1.02979 (19)0.0863 (10)
H43A0.2849600.6548401.0727240.104*
H43B0.3200420.5315851.0498030.104*
C440.1453 (4)0.5818 (4)1.0156 (2)0.1313 (17)
H44A0.1397490.5300150.9728390.197*
H44B0.1040130.6518790.9988070.197*
H44C0.1054630.5506421.0661150.197*
C450.3515 (3)0.7704 (3)0.9396 (2)0.0747 (9)
H45A0.4353590.7925520.9208210.090*
H45B0.3317270.8043840.9916590.090*
C460.2599 (3)0.8153 (3)0.8763 (3)0.1022 (12)
H46A0.2794440.7827550.8242720.153*
H46B0.2655740.8958250.8689170.153*
H46C0.1762860.7961090.8952830.153*
C20.6454 (3)−0.0609 (2)0.60257 (18)0.0752 (9)
C30.7001 (5)−0.1017 (3)0.5287 (2)0.1132 (15)
H30.697501−0.1783850.5207800.136*
C40.7556 (4)−0.0329 (3)0.4695 (2)0.1091 (14)
H40.790806−0.0626570.4217040.131*
C50.7612 (3)0.0854 (3)0.47927 (18)0.0736 (9)
C60.7043 (3)0.1275 (2)0.55203 (16)0.0640 (8)
H60.7040110.2045560.5588610.077*
C70.6496 (3)0.0568 (2)0.61259 (16)0.0595 (7)
C80.7027 (3)0.0022 (2)0.80481 (17)0.0607 (7)
C90.7525 (3)−0.1014 (3)0.83307 (19)0.0749 (9)
H90.710055−0.1664180.8239030.090*
C100.8643 (4)−0.1113 (4)0.8748 (2)0.0990 (12)
H100.896208−0.1820340.8923400.119*
C110.9272 (4)−0.0162 (5)0.8900 (2)0.1057 (13)
H111.001230−0.0225990.9185130.127*
C120.8820 (4)0.0869 (4)0.8635 (3)0.1111 (14)
H120.9251090.1512700.8733400.133*
C130.7716 (3)0.0957 (3)0.8218 (2)0.0878 (10)
H130.7415210.1670750.8042790.105*
C140.4570 (2)0.0692 (2)0.80939 (16)0.0516 (6)
C150.4528 (3)0.0731 (2)0.89529 (16)0.0577 (7)
H150.5231630.0495530.9244710.069*
C160.3469 (3)0.1109 (2)0.93871 (19)0.0686 (8)
H160.3469430.1128590.9962140.082*
C170.2422 (3)0.1453 (3)0.8971 (2)0.0777 (9)
H170.1707080.1700220.9262560.093*
C180.2428 (3)0.1432 (3)0.8124 (2)0.0801 (9)
H180.1717880.1668230.7839910.096*
C190.3491 (3)0.1058 (2)0.76901 (19)0.0669 (8)
H190.3483980.1052270.7114520.080*
C200.8804 (4)0.1091 (3)0.3436 (2)0.1040 (13)
H20A0.8828250.1695800.3002280.125*
H20B0.8302990.0495680.3250290.125*
C211.0107 (6)0.0647 (5)0.3574 (3)0.185 (3)
H21A1.0472920.0397310.3061990.278*
H21B1.0082220.0025400.3984640.278*
H21C1.0602960.1232540.3763360.278*
C220.8287 (4)0.2749 (3)0.4276 (2)0.0998 (12)
H22A0.8329080.2908730.4855170.120*
H22B0.9044460.3019530.3983840.120*
C230.7185 (5)0.3336 (4)0.3917 (4)0.151 (2)
H23A0.7239360.4131350.3973320.227*
H23B0.6435850.3063890.4204680.227*
H23C0.7159120.3195420.3339210.227*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0925 (15)0.0455 (10)0.0604 (12)−0.0145 (9)0.0079 (10)−0.0031 (9)
N10.112 (2)0.0756 (18)0.0584 (15)−0.0104 (15)0.0241 (15)−0.0058 (13)
C10.120 (3)0.0468 (16)0.0630 (19)−0.0167 (17)−0.0004 (18)−0.0103 (14)
B10.063 (2)0.0452 (16)0.0575 (18)−0.0090 (14)0.0031 (15)−0.0031 (14)
O20.0827 (13)0.0440 (10)0.0532 (11)−0.0112 (9)0.0139 (9)−0.0054 (8)
N20.0601 (15)0.0826 (18)0.0561 (14)−0.0031 (12)0.0089 (12)−0.0027 (12)
B20.0564 (18)0.0409 (15)0.0593 (18)0.0003 (13)0.0050 (15)−0.0045 (13)
O30.0817 (14)0.0476 (10)0.0655 (12)−0.0067 (9)0.0066 (11)−0.0067 (9)
O40.0563 (11)0.0435 (9)0.0586 (11)−0.0032 (8)0.0111 (9)0.0036 (8)
C240.0701 (19)0.0446 (15)0.0642 (18)−0.0079 (13)−0.0086 (15)0.0028 (13)
C250.0535 (15)0.0445 (14)0.0585 (16)−0.0050 (12)−0.0050 (13)0.0045 (12)
C260.0685 (19)0.0525 (16)0.0717 (19)−0.0119 (14)0.0004 (15)0.0133 (14)
C270.0657 (19)0.0707 (19)0.0639 (18)−0.0080 (15)0.0100 (15)0.0143 (15)
C280.0471 (15)0.0621 (17)0.0527 (15)−0.0036 (12)−0.0014 (12)0.0028 (13)
C290.0499 (15)0.0432 (13)0.0563 (15)−0.0023 (11)0.0017 (12)0.0016 (12)
C300.0408 (13)0.0469 (14)0.0514 (14)−0.0048 (11)−0.0041 (11)0.0038 (11)
C310.0614 (17)0.0638 (17)0.0472 (15)0.0045 (14)0.0063 (13)0.0036 (13)
C320.092 (3)0.092 (2)0.074 (2)0.035 (2)0.0040 (19)−0.0008 (18)
C330.098 (3)0.158 (5)0.087 (3)0.067 (3)0.001 (2)0.009 (3)
C340.064 (3)0.226 (6)0.068 (3)0.012 (3)0.0014 (19)0.009 (3)
C350.081 (3)0.150 (4)0.087 (3)−0.032 (3)−0.014 (2)0.002 (3)
C360.075 (2)0.083 (2)0.081 (2)−0.0115 (18)−0.0165 (18)0.0019 (18)
C370.0593 (17)0.0441 (14)0.0552 (15)−0.0008 (12)−0.0014 (13)−0.0037 (11)
C380.068 (2)0.107 (3)0.0634 (19)0.0043 (18)0.0069 (16)0.0151 (17)
C390.090 (3)0.120 (3)0.068 (2)0.003 (2)0.019 (2)0.016 (2)
C400.121 (3)0.075 (2)0.0520 (18)−0.001 (2)0.000 (2)0.0031 (15)
C410.097 (3)0.086 (2)0.065 (2)−0.0049 (19)−0.0242 (19)−0.0045 (17)
C420.070 (2)0.075 (2)0.0646 (19)−0.0096 (15)−0.0085 (16)−0.0056 (15)
C430.085 (2)0.119 (3)0.0552 (18)−0.007 (2)0.0077 (17)−0.0071 (18)
C440.081 (3)0.222 (5)0.089 (3)−0.042 (3)0.018 (2)0.004 (3)
C450.067 (2)0.075 (2)0.084 (2)−0.0118 (16)0.0163 (17)−0.0291 (17)
C460.075 (2)0.070 (2)0.161 (4)0.0040 (18)−0.010 (2)0.001 (2)
C20.124 (3)0.0470 (16)0.0546 (17)−0.0147 (16)0.0106 (17)−0.0072 (13)
C30.218 (5)0.0530 (19)0.068 (2)−0.019 (2)0.026 (3)−0.0160 (17)
C40.201 (4)0.066 (2)0.058 (2)−0.003 (2)0.031 (2)−0.0157 (17)
C50.104 (2)0.0641 (19)0.0519 (17)−0.0083 (17)0.0107 (16)−0.0035 (14)
C60.088 (2)0.0499 (15)0.0541 (16)−0.0097 (14)0.0108 (15)−0.0047 (13)
C70.080 (2)0.0506 (16)0.0479 (15)−0.0087 (14)0.0052 (14)−0.0071 (12)
C80.0573 (17)0.0616 (17)0.0621 (17)0.0040 (14)0.0142 (14)−0.0098 (14)
C90.072 (2)0.082 (2)0.068 (2)0.0098 (17)0.0097 (17)0.0014 (16)
C100.084 (3)0.122 (3)0.086 (3)0.032 (2)0.010 (2)0.009 (2)
C110.065 (2)0.161 (4)0.092 (3)0.022 (3)−0.004 (2)−0.025 (3)
C120.063 (2)0.129 (4)0.146 (4)0.005 (2)−0.011 (2)−0.046 (3)
C130.065 (2)0.084 (2)0.118 (3)0.0039 (18)−0.010 (2)−0.026 (2)
C140.0516 (15)0.0459 (14)0.0561 (16)−0.0074 (11)0.0000 (12)0.0067 (11)
C150.0536 (16)0.0622 (17)0.0550 (16)0.0028 (13)0.0038 (13)0.0078 (13)
C160.068 (2)0.0730 (19)0.0616 (18)0.0023 (15)0.0165 (15)0.0040 (15)
C170.058 (2)0.073 (2)0.097 (3)0.0061 (15)0.0165 (18)0.0113 (18)
C180.0563 (19)0.080 (2)0.102 (3)0.0042 (16)−0.0100 (18)0.0170 (19)
C190.0656 (19)0.0669 (18)0.0668 (18)−0.0041 (15)−0.0071 (15)0.0095 (14)
C200.152 (4)0.102 (3)0.055 (2)−0.004 (3)0.021 (2)−0.0012 (18)
C210.173 (5)0.236 (7)0.130 (4)0.085 (5)0.069 (4)0.022 (4)
C220.117 (3)0.100 (3)0.081 (2)−0.040 (2)0.033 (2)−0.008 (2)
C230.154 (5)0.105 (4)0.189 (5)0.016 (3)0.040 (4)−0.002 (3)
Geometric parameters (Å, º) top
O1—C11.279 (3)C43—H43B0.9700
O1—B11.562 (3)C43—C441.497 (5)
N1—C51.341 (4)C44—H44A0.9600
N1—C201.490 (4)C44—H44B0.9600
N1—C221.477 (4)C44—H44C0.9600
C1—H10.9300C45—H45A0.9700
C1—C21.370 (4)C45—H45B0.9700
B1—O21.504 (3)C45—C461.507 (5)
B1—C81.593 (4)C46—H46A0.9600
B1—C141.606 (4)C46—H46B0.9600
O2—C71.328 (3)C46—H46C0.9600
N2—C281.353 (3)C2—C31.414 (4)
N2—C431.481 (4)C2—C71.422 (4)
N2—C451.474 (4)C3—H30.9300
B2—O31.557 (3)C3—C41.345 (5)
B2—O41.510 (3)C4—H40.9300
B2—C311.600 (4)C4—C51.430 (4)
B2—C371.608 (4)C5—C61.414 (4)
O3—C241.286 (3)C6—H60.9300
O4—C301.327 (3)C6—C71.369 (3)
C24—H240.9300C8—C91.386 (4)
C24—C251.372 (4)C8—C131.398 (4)
C25—C261.415 (4)C9—H90.9300
C25—C301.430 (3)C9—C101.394 (5)
C26—H260.9300C10—H100.9300
C26—C271.350 (4)C10—C111.372 (6)
C27—H270.9300C11—H110.9300
C27—C281.428 (4)C11—C121.354 (6)
C28—C291.411 (3)C12—H120.9300
C29—H290.9300C12—C131.380 (5)
C29—C301.373 (3)C13—H130.9300
C31—C321.389 (4)C14—C151.389 (4)
C31—C361.390 (4)C14—C191.392 (4)
C32—H320.9300C15—H150.9300
C32—C331.395 (6)C15—C161.385 (4)
C33—H330.9300C16—H160.9300
C33—C341.364 (6)C16—C171.367 (4)
C34—H340.9300C17—H170.9300
C34—C351.336 (6)C17—C181.368 (4)
C35—H350.9300C18—H180.9300
C35—C361.383 (5)C18—C191.386 (4)
C36—H360.9300C19—H190.9300
C37—C381.378 (4)C20—H20A0.9700
C37—C421.378 (4)C20—H20B0.9700
C38—H380.9300C20—C211.494 (6)
C38—C391.389 (4)C21—H21A0.9600
C39—H390.9300C21—H21B0.9600
C39—C401.358 (5)C21—H21C0.9600
C40—H400.9300C22—H22A0.9700
C40—C411.355 (5)C22—H22B0.9700
C41—H410.9300C22—C231.471 (6)
C41—C421.376 (4)C23—H23A0.9600
C42—H420.9300C23—H23B0.9600
C43—H43A0.9700C23—H23C0.9600
C1—O1—B1117.3 (2)H44A—C44—H44C109.5
C5—N1—C20123.0 (3)H44B—C44—H44C109.5
C5—N1—C22122.1 (3)N2—C45—H45A108.9
C22—N1—C20114.9 (3)N2—C45—H45B108.9
O1—C1—H1117.7N2—C45—C46113.3 (3)
O1—C1—C2124.6 (3)H45A—C45—H45B107.7
C2—C1—H1117.7C46—C45—H45A108.9
O1—B1—C8107.7 (2)C46—C45—H45B108.9
O1—B1—C14105.8 (2)C45—C46—H46A109.5
O2—B1—O1108.1 (2)C45—C46—H46B109.5
O2—B1—C8111.0 (2)C45—C46—H46C109.5
O2—B1—C14107.4 (2)H46A—C46—H46B109.5
C8—B1—C14116.4 (2)H46A—C46—H46C109.5
C7—O2—B1119.3 (2)H46B—C46—H46C109.5
C28—N2—C43122.1 (3)C1—C2—C3122.5 (3)
C28—N2—C45121.3 (2)C1—C2—C7119.6 (3)
C45—N2—C43116.5 (2)C3—C2—C7117.8 (3)
O3—B2—C31107.8 (2)C2—C3—H3119.1
O3—B2—C37106.8 (2)C4—C3—C2121.9 (3)
O4—B2—O3107.9 (2)C4—C3—H3119.1
O4—B2—C31110.8 (2)C3—C4—H4119.6
O4—B2—C37108.3 (2)C3—C4—C5120.7 (3)
C31—B2—C37115.0 (2)C5—C4—H4119.6
C24—O3—B2118.3 (2)N1—C5—C4119.8 (3)
C30—O4—B2120.12 (19)N1—C5—C6122.3 (3)
O3—C24—H24117.7C6—C5—C4117.8 (3)
O3—C24—C25124.6 (2)C5—C6—H6119.4
C25—C24—H24117.7C7—C6—C5121.1 (3)
C24—C25—C26123.0 (2)C7—C6—H6119.4
C24—C25—C30118.9 (2)O2—C7—C2118.6 (2)
C26—C25—C30117.8 (2)O2—C7—C6120.8 (2)
C25—C26—H26119.0C6—C7—C2120.6 (2)
C27—C26—C25121.9 (3)C9—C8—B1125.0 (3)
C27—C26—H26119.0C9—C8—C13115.4 (3)
C26—C27—H27119.6C13—C8—B1119.6 (3)
C26—C27—C28120.8 (2)C8—C9—H9119.0
C28—C27—H27119.6C8—C9—C10122.0 (3)
N2—C28—C27120.8 (2)C10—C9—H9119.0
N2—C28—C29121.4 (2)C9—C10—H10120.1
C29—C28—C27117.8 (2)C11—C10—C9119.8 (4)
C28—C29—H29119.2C11—C10—H10120.1
C30—C29—C28121.6 (2)C10—C11—H11119.9
C30—C29—H29119.2C12—C11—C10120.3 (4)
O4—C30—C25119.0 (2)C12—C11—H11119.9
O4—C30—C29120.8 (2)C11—C12—H12120.3
C29—C30—C25120.0 (2)C11—C12—C13119.5 (4)
C32—C31—B2124.0 (3)C13—C12—H12120.3
C32—C31—C36115.6 (3)C8—C13—H13118.5
C36—C31—B2120.0 (3)C12—C13—C8123.0 (4)
C31—C32—H32119.4C12—C13—H13118.5
C31—C32—C33121.2 (4)C15—C14—B1123.5 (2)
C33—C32—H32119.4C15—C14—C19116.5 (2)
C32—C33—H33119.7C19—C14—B1119.9 (2)
C34—C33—C32120.6 (4)C14—C15—H15119.0
C34—C33—H33119.7C16—C15—C14121.9 (3)
C33—C34—H34120.2C16—C15—H15119.0
C35—C34—C33119.5 (5)C15—C16—H16120.0
C35—C34—H34120.2C17—C16—C15120.0 (3)
C34—C35—H35119.7C17—C16—H16120.0
C34—C35—C36120.7 (4)C16—C17—H17120.1
C36—C35—H35119.7C16—C17—C18119.8 (3)
C31—C36—H36118.8C18—C17—H17120.1
C35—C36—C31122.3 (4)C17—C18—H18120.0
C35—C36—H36118.8C17—C18—C19120.1 (3)
C38—C37—B2123.9 (3)C19—C18—H18120.0
C38—C37—C42115.7 (3)C14—C19—H19119.2
C42—C37—B2120.4 (2)C18—C19—C14121.7 (3)
C37—C38—H38118.9C18—C19—H19119.2
C37—C38—C39122.2 (3)N1—C20—H20A109.3
C39—C38—H38118.9N1—C20—H20B109.3
C38—C39—H39120.0N1—C20—C21111.6 (3)
C40—C39—C38120.1 (3)H20A—C20—H20B108.0
C40—C39—H39120.0C21—C20—H20A109.3
C39—C40—H40120.5C21—C20—H20B109.3
C41—C40—C39119.1 (3)C20—C21—H21A109.5
C41—C40—H40120.5C20—C21—H21B109.5
C40—C41—H41119.7C20—C21—H21C109.5
C40—C41—C42120.6 (3)H21A—C21—H21B109.5
C42—C41—H41119.7H21A—C21—H21C109.5
C37—C42—H42118.8H21B—C21—H21C109.5
C41—C42—C37122.4 (3)N1—C22—H22A109.6
C41—C42—H42118.8N1—C22—H22B109.6
N2—C43—H43A108.9H22A—C22—H22B108.1
N2—C43—H43B108.9C23—C22—N1110.2 (4)
N2—C43—C44113.3 (3)C23—C22—H22A109.6
H43A—C43—H43B107.7C23—C22—H22B109.6
C44—C43—H43A108.9C22—C23—H23A109.5
C44—C43—H43B108.9C22—C23—H23B109.5
C43—C44—H44A109.5C22—C23—H23C109.5
C43—C44—H44B109.5H23A—C23—H23B109.5
C43—C44—H44C109.5H23A—C23—H23C109.5
H44A—C44—H44B109.5H23B—C23—H23C109.5
O1—C1—C2—C3177.0 (4)C31—B2—O4—C30−79.9 (3)
O1—C1—C2—C7−7.5 (5)C31—B2—C37—C388.7 (4)
O1—B1—O2—C7−40.4 (3)C31—B2—C37—C42−172.0 (2)
O1—B1—C8—C9−13.0 (4)C31—C32—C33—C340.3 (6)
O1—B1—C8—C13167.9 (2)C32—C31—C36—C350.4 (4)
O1—B1—C14—C15105.6 (3)C32—C33—C34—C350.8 (7)
O1—B1—C14—C19−71.5 (3)C33—C34—C35—C36−1.3 (6)
N1—C5—C6—C7−176.8 (3)C34—C35—C36—C310.7 (5)
C1—O1—B1—O233.7 (3)C36—C31—C32—C33−0.9 (4)
C1—O1—B1—C8−86.4 (3)C37—B2—O3—C24−147.9 (2)
C1—O1—B1—C14148.5 (3)C37—B2—O4—C30153.1 (2)
C1—C2—C3—C4176.2 (4)C37—B2—C31—C32−96.0 (3)
C1—C2—C7—O21.3 (5)C37—B2—C31—C3677.3 (3)
C1—C2—C7—C6−175.3 (3)C37—C38—C39—C400.9 (6)
B1—O1—C1—C2−12.1 (5)C38—C37—C42—C41−0.8 (4)
B1—O2—C7—C224.8 (4)C38—C39—C40—C41−0.7 (6)
B1—O2—C7—C6−158.6 (3)C39—C40—C41—C42−0.2 (5)
B1—C8—C9—C10−179.7 (3)C40—C41—C42—C371.0 (5)
B1—C8—C13—C12179.4 (3)C42—C37—C38—C39−0.2 (5)
B1—C14—C15—C16−177.0 (2)C43—N2—C28—C274.5 (4)
B1—C14—C19—C18176.8 (3)C43—N2—C28—C29−175.7 (2)
O2—B1—C8—C9−131.1 (3)C43—N2—C45—C46−100.7 (3)
O2—B1—C8—C1349.8 (3)C45—N2—C28—C27−172.7 (3)
O2—B1—C14—C15−139.1 (2)C45—N2—C28—C297.1 (4)
O2—B1—C14—C1943.8 (3)C45—N2—C43—C4489.6 (4)
N2—C28—C29—C30177.7 (2)C2—C3—C4—C5−0.2 (7)
B2—O3—C24—C2510.8 (4)C3—C2—C7—O2177.0 (3)
B2—O4—C30—C25−22.6 (3)C3—C2—C7—C60.4 (5)
B2—O4—C30—C29160.8 (2)C3—C4—C5—N1177.8 (4)
B2—C31—C32—C33172.7 (3)C3—C4—C5—C6−1.3 (6)
B2—C31—C36—C35−173.4 (3)C4—C5—C6—C72.3 (5)
B2—C37—C38—C39179.2 (3)C5—N1—C20—C21−85.1 (5)
B2—C37—C42—C41179.8 (3)C5—N1—C22—C23−87.7 (4)
O3—B2—O4—C3037.9 (3)C5—C6—C7—O2−178.4 (3)
O3—B2—C31—C3223.0 (3)C5—C6—C7—C2−1.9 (5)
O3—B2—C31—C36−163.8 (2)C7—C2—C3—C40.6 (6)
O3—B2—C37—C38−110.8 (3)C8—B1—O2—C777.5 (3)
O3—B2—C37—C4268.5 (3)C8—B1—C14—C15−13.9 (4)
O3—C24—C25—C26−177.4 (3)C8—B1—C14—C19168.9 (2)
O3—C24—C25—C308.6 (4)C8—C9—C10—C111.0 (5)
O4—B2—O3—C24−31.6 (3)C9—C8—C13—C120.3 (5)
O4—B2—C31—C32140.8 (3)C9—C10—C11—C12−0.9 (6)
O4—B2—C31—C36−45.9 (3)C10—C11—C12—C130.6 (6)
O4—B2—C37—C38133.2 (3)C11—C12—C13—C8−0.3 (6)
O4—B2—C37—C42−47.5 (3)C13—C8—C9—C10−0.6 (4)
C24—C25—C26—C27−175.9 (3)C14—B1—O2—C7−154.2 (2)
C24—C25—C30—O4−2.8 (4)C14—B1—C8—C9105.5 (3)
C24—C25—C30—C29173.9 (2)C14—B1—C8—C13−73.5 (3)
C25—C26—C27—C282.0 (5)C14—C15—C16—C170.3 (4)
C26—C25—C30—O4−177.1 (2)C15—C14—C19—C18−0.6 (4)
C26—C25—C30—C29−0.5 (4)C15—C16—C17—C18−0.6 (5)
C26—C27—C28—N2180.0 (3)C16—C17—C18—C190.3 (5)
C26—C27—C28—C290.1 (4)C17—C18—C19—C140.3 (5)
C27—C28—C29—C30−2.5 (4)C19—C14—C15—C160.2 (4)
C28—N2—C43—C44−87.7 (4)C20—N1—C5—C41.3 (5)
C28—N2—C45—C4676.7 (3)C20—N1—C5—C6−179.7 (3)
C28—C29—C30—O4179.2 (2)C20—N1—C22—C2390.9 (4)
C28—C29—C30—C252.6 (4)C22—N1—C5—C4179.7 (4)
C30—C25—C26—C27−1.8 (4)C22—N1—C5—C6−1.2 (5)
C31—B2—O3—C2488.0 (3)C22—N1—C20—C2196.3 (4)
Hydrogen-bond geometry (Å, º) top
Cg3, Cg4, Cg7, Cg8 and Cg9 are the centroids of rings C3–C13, C14–C19, C25–C30, C31–C36 and C37–C42, respectively.
D—H···AD—HH···AD···AD—H···A
C24—H24···O20.932.513.343 (3)149
C1—H1···O4i0.932.553.334 (3)142
C3—H3···Cg9i0.932.593.510 (4)169
C23—H23A···Cg90.962.883.771 (5)155
C26—H26···Cg40.932.663.562 (3)164
C46—H46B···Cg4ii0.962.693.623 (4)164
C21—H21A···Cg3iii0.962.873.815 (5)168
C43—H43B···Cg7iv0.962.933.626 (3)129
C44—H44C···Cg8iv0.962.953.876 (4)162
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z; (iii) −x+2, −y, −z+1; (iv) −x+1, −y+1, −z+2.
Photophysical data of examined compounds (in CHCl3, 10 µM) top
CompoundAbsorptionEmissionStokes shift
λabs (nm) / (ε 103 M-1.cm-1)λem (nm)Intensity (a.u.)Δν (cm-1)
Et2N-CHO343 (111)425224-
Et2N-Bz436 (65); 504 (5)481 / 51019533 / 185163327
complex (I)347 (73)432273495670
 

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