# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_6058
_database_code_depnum_ccdc_archive 'CCDC 1030235'

_audit_update_record             
;
2014-10-20 deposited with the CCDC.
2015-04-24 downloaded from the CCDC.
;
_audit_creation_method           'manual editing of SHELXL97.CIF'

#=====================================================================

_chemical_name_systematic        
;
Selective Endocytic Trafficking in Live Cells with Fluorescent Oxazoles 
and their Boron Complexes.

;


_chemical_formula_sum            'C22 H19 N O3'
_chemical_formula_weight         345.38
_cell_length_a                   17.7444(13)
_cell_length_b                   10.3307(6)
_cell_length_c                   18.7617(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3439.2(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_exptl_crystal_density_diffrn    1.334
_refine_ls_R_factor_gt           0.0599


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.09260(10) -0.2329(2) 0.85378(12) 0.0885(6) Uani 1 1 d . . .
H1 H 0.1061 -0.1796 0.8240 0.133 Uiso 1 1 calc R . .
O2 O 0.30965(8) -0.14147(13) 0.78183(7) 0.0531(4) Uani 1 1 d . A .
N1 N 0.18532(10) -0.10870(15) 0.76697(9) 0.0491(4) Uani 1 1 d . . .
C1 C 0.15229(14) -0.3017(2) 0.87559(13) 0.0607(6) Uani 1 1 d . . .
C2 C 0.13966(18) -0.4007(3) 0.92431(14) 0.0788(8) Uani 1 1 d . . .
H2 H 0.0910 -0.4178 0.9401 0.095 Uiso 1 1 calc R . .
C3 C 0.1988(2) -0.4732(2) 0.94914(15) 0.0810(8) Uani 1 1 d . . .
H3 H 0.1899 -0.5388 0.9820 0.097 Uiso 1 1 calc R . .
C4 C 0.27147(18) -0.4502(2) 0.92597(15) 0.0753(8) Uani 1 1 d . . .
H4 H 0.3112 -0.5003 0.9428 0.090 Uiso 1 1 calc R . .
C5 C 0.28441(15) -0.3524(2) 0.87771(13) 0.0632(6) Uani 1 1 d . . .
H5 H 0.3333 -0.3361 0.8622 0.076 Uiso 1 1 calc R . .
C6 C 0.22511(13) -0.27740(19) 0.85178(11) 0.0509(5) Uani 1 1 d . . .
C7 C 0.23734(12) -0.1755(2) 0.79993(11) 0.0483(5) Uani 1 1 d . . .
C8 C 0.22503(11) -0.02322(19) 0.72342(11) 0.0465(5) Uani 1 1 d . A .
C9 C 0.19939(11) 0.07241(18) 0.67535(11) 0.0475(5) Uani 1 1 d . . .
C10 C 0.12255(13) 0.0994(2) 0.66138(13) 0.0586(6) Uani 1 1 d . . .
H10 H 0.0853 0.0531 0.6851 0.070 Uiso 1 1 calc R . .
C11 C 0.10259(14) 0.1922(2) 0.61368(15) 0.0670(7) Uani 1 1 d . . .
H11 H 0.0519 0.2087 0.6049 0.080 Uiso 1 1 calc R . .
C12 C 0.15741(14) 0.2627(2) 0.57791(14) 0.0636(6) Uani 1 1 d . . .
H12 H 0.1431 0.3257 0.5452 0.076 Uiso 1 1 calc R . .
C13 C 0.23256(13) 0.2404(2) 0.59022(12) 0.0550(6) Uani 1 1 d . . .
H13 H 0.2686 0.2889 0.5662 0.066 Uiso 1 1 calc R . .
C14 C 0.25527(11) 0.14482(19) 0.63889(11) 0.0475(5) Uani 1 1 d . . .
C15 C 0.33386(12) 0.1192(2) 0.65253(11) 0.0523(5) Uani 1 1 d . . .
O3 O 0.38145(9) 0.19680(17) 0.61477(10) 0.0761(6) Uani 1 1 d . A .
C18 C 0.46185(12) 0.1756(2) 0.62045(13) 0.0545(6) Uani 1 1 d . . .
C20 C 0.44028(13) 0.0019(3) 0.71217(15) 0.0800(8) Uani 1 1 d . . .
C16 C 0.35826(12) 0.0260(2) 0.69914(11) 0.0515(5) Uani 1 1 d . A .
C17 C 0.30041(12) -0.04260(19) 0.73311(10) 0.0474(5) Uani 1 1 d . . .
C19B C 0.4845(2) 0.1387(4) 0.6935(2) 0.0591(12) Uani 0.555(4) 1 d P A 1
H19C H 0.4702 0.2057 0.7271 0.071 Uiso 0.555(4) 1 calc PR A 1
H19D H 0.5386 0.1265 0.6961 0.071 Uiso 0.555(4) 1 calc PR A 1
C21B C 0.4747(3) 0.0817(5) 0.5634(3) 0.0734(14) Uani 0.555(4) 1 d P A 1
H21D H 0.4447 0.0060 0.5719 0.110 Uiso 0.555(4) 1 calc PR A 1
H21E H 0.5270 0.0581 0.5625 0.110 Uiso 0.555(4) 1 calc PR A 1
H21F H 0.4609 0.1194 0.5185 0.110 Uiso 0.555(4) 1 calc PR A 1
C22B C 0.4987(3) 0.3101(4) 0.5996(3) 0.0708(14) Uani 0.555(4) 1 d P A 1
H22D H 0.4771 0.3405 0.5558 0.106 Uiso 0.555(4) 1 calc PR A 1
H22E H 0.5520 0.2993 0.5937 0.106 Uiso 0.555(4) 1 calc PR A 1
H22F H 0.4892 0.3720 0.6368 0.106 Uiso 0.555(4) 1 calc PR A 1
C19A C 0.4833(3) 0.0284(4) 0.6402(3) 0.0558(14) Uani 0.445(4) 1 d P A 2
H19A H 0.4667 -0.0306 0.6032 0.067 Uiso 0.445(4) 1 calc PR A 2
H19B H 0.5373 0.0189 0.6465 0.067 Uiso 0.445(4) 1 calc PR A 2
C21A C 0.4973(3) 0.2116(6) 0.5519(3) 0.0748(19) Uani 0.445(4) 1 d P A 2
H21A H 0.4778 0.1573 0.5146 0.112 Uiso 0.445(4) 1 calc PR A 2
H21B H 0.5509 0.2003 0.5552 0.112 Uiso 0.445(4) 1 calc PR A 2
H21C H 0.4862 0.3005 0.5413 0.112 Uiso 0.445(4) 1 calc PR A 2
C22A C 0.4816(3) 0.2598(5) 0.6813(3) 0.0726(18) Uani 0.445(4) 1 d P A 2
H22A H 0.4628 0.3455 0.6729 0.109 Uiso 0.445(4) 1 calc PR A 2
H22B H 0.5354 0.2628 0.6865 0.109 Uiso 0.445(4) 1 calc PR A 2
H22C H 0.4595 0.2257 0.7241 0.109 Uiso 0.445(4) 1 calc PR A 2
H20C H 0.4581 -0.0658 0.6819 0.076 Uiso 0.445(4) 1 d P A 1
H20D H 0.4483 -0.0202 0.7614 0.076 Uiso 0.445(4) 1 d P A 1
H20A H 0.4481 -0.0844 0.7280 0.076 Uiso 0.555(4) 1 d P A 2
H20B H 0.4580 0.0622 0.7486 0.076 Uiso 0.555(4) 1 d P A 2


_geom_special_details            
;
 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.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.340(3) . ?
O1 H1 0.8200 . ?
O2 C7 1.373(2) . ?
O2 C17 1.380(2) . ?
N1 C7 1.308(3) . ?
N1 C8 1.394(2) . ?
C1 C6 1.390(3) . ?
C1 C2 1.390(3) . ?
C2 C3 1.372(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.450(3) . ?
C8 C17 1.365(3) . ?
C8 C9 1.413(3) . ?
C9 C10 1.416(3) . ?
C9 C14 1.418(3) . ?
C10 C11 1.358(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.388(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.404(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.442(3) . ?
C15 O3 1.363(3) . ?
C15 C16 1.371(3) . ?
O3 C18 1.447(3) . ?
C18 C21B 1.462(5) . ?
C18 C22A 1.478(6) . ?
C18 C19B 1.478(5) . ?
C18 C21A 1.480(6) . ?
C18 C22B 1.585(5) . ?
C18 C19A 1.611(5) . ?
C20 C16 1.497(3) . ?
C20 C19A 1.575(5) . ?
C20 C19B 1.655(5) . ?
C20 H20C 0.955(3) . ?
C20 H20D 0.961(3) . ?
C20 H20A 0.950(3) . ?
C20 H20B 0.978(3) . ?
C16 C17 1.401(3) . ?
C19B H19C 0.9700 . ?
C19B H19D 0.9700 . ?
C19B H20B 1.384(4) . ?
C21B H21D 0.9600 . ?
C21B H21E 0.9600 . ?
C21B H21F 0.9600 . ?
C22B H22D 0.9600 . ?
C22B H22E 0.9600 . ?
C22B H22F 0.9600 . ?
C19A H19A 0.9700 . ?
C19A H19B 0.9700 . ?
C19A H20C 1.326(5) . ?
C21A H21A 0.9600 . ?
C21A H21B 0.9600 . ?
C21A H21C 0.9600 . ?
C22A H22A 0.9600 . ?
C22A H22B 0.9600 . ?
C22A H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C7 O2 C17 104.02(16) . . ?
C7 N1 C8 104.75(17) . . ?
O1 C1 C6 122.8(2) . . ?
O1 C1 C2 117.6(2) . . ?
C6 C1 C2 119.6(3) . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 119.3(2) . . ?
C1 C6 C7 119.1(2) . . ?
C5 C6 C7 121.6(2) . . ?
N1 C7 O2 114.04(18) . . ?
N1 C7 C6 126.50(19) . . ?
O2 C7 C6 119.46(19) . . ?
C17 C8 N1 108.93(18) . . ?
C17 C8 C9 120.21(19) . . ?
N1 C8 C9 130.86(19) . . ?
C8 C9 C10 124.5(2) . . ?
C8 C9 C14 116.85(18) . . ?
C10 C9 C14 118.7(2) . . ?
C11 C10 C9 120.8(2) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.4(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C9 118.95(19) . . ?
C13 C14 C15 121.5(2) . . ?
C9 C14 C15 119.59(19) . . ?
O3 C15 C16 123.3(2) . . ?
O3 C15 C14 113.51(18) . . ?
C16 C15 C14 123.19(19) . . ?
C15 O3 C18 118.91(17) . . ?
O3 C18 C21B 101.6(3) . . ?
O3 C18 C22A 101.6(3) . . ?
C21B C18 C22A 156.8(3) . . ?
O3 C18 C19B 112.0(2) . . ?
C21B C18 C19B 117.7(3) . . ?
C22A C18 C19B 51.0(3) . . ?
O3 C18 C21A 108.5(3) . . ?
C21B C18 C21A 57.6(3) . . ?
C22A C18 C21A 115.0(4) . . ?
C19B C18 C21A 139.1(3) . . ?
O3 C18 C22B 104.8(2) . . ?
C21B C18 C22B 109.7(3) . . ?
C22A C18 C22B 64.9(3) . . ?
C19B C18 C22B 110.0(3) . . ?
C21A C18 C22B 52.4(3) . . ?
O3 C18 C19A 113.1(2) . . ?
C21B C18 C19A 60.3(3) . . ?
C22A C18 C19A 108.7(3) . . ?
C19B C18 C19A 58.6(3) . . ?
C21A C18 C19A 109.7(3) . . ?
C22B C18 C19A 141.9(3) . . ?
C16 C20 C19A 107.6(3) . . ?
C16 C20 C19B 106.5(2) . . ?
C19A C20 C19B 55.9(2) . . ?
C16 C20 H20C 110.2(2) . . ?
C19A C20 H20C 57.1(2) . . ?
C19B C20 H20C 110.1(2) . . ?
C16 C20 H20D 109.9(2) . . ?
C19A C20 H20D 142.4(3) . . ?
C19B C20 H20D 109.6(3) . . ?
H20C C20 H20D 110.5(2) . . ?
C16 C20 H20A 110.5(2) . . ?
C19A C20 H20A 111.1(3) . . ?
C19B C20 H20A 143.0(3) . . ?
H20C C20 H20A 56.70(17) . . ?
H20D C20 H20A 57.00(14) . . ?
C16 C20 H20B 108.7(2) . . ?
C19A C20 H20B 109.4(3) . . ?
C19B C20 H20B 56.65(19) . . ?
H20C C20 H20B 141.0(3) . . ?
H20D C20 H20B 55.37(16) . . ?
H20A C20 H20B 109.4(3) . . ?
C15 C16 C17 114.47(19) . . ?
C15 C16 C20 121.9(2) . . ?
C17 C16 C20 123.6(2) . . ?
C8 C17 O2 108.24(17) . . ?
C8 C17 C16 125.7(2) . . ?
O2 C17 C16 126.06(19) . . ?
C18 C19B C20 106.7(3) . . ?
C18 C19B H19C 110.4 . . ?
C20 C19B H19C 110.4 . . ?
C18 C19B H19D 110.4 . . ?
C20 C19B H19D 110.4 . . ?
H19C C19B H19D 108.6 . . ?
C18 C19B H20B 138.4(3) . . ?
C20 C19B H20B 36.17(14) . . ?
H19C C19B H20B 80.4 . . ?
H19D C19B H20B 103.0 . . ?
C18 C21B H21D 109.5 . . ?
C18 C21B H21E 109.5 . . ?
C18 C21B H21F 109.5 . . ?
C18 C22B H22D 109.5 . . ?
C18 C22B H22E 109.5 . . ?
C18 C22B H22F 109.5 . . ?
C20 C19A C18 104.3(3) . . ?
C20 C19A H19A 110.9 . . ?
C18 C19A H19A 110.9 . . ?
C20 C19A H19B 110.9 . . ?
C18 C19A H19B 110.9 . . ?
H19A C19A H19B 108.9 . . ?
C20 C19A H20C 37.20(17) . . ?
C18 C19A H20C 138.5(3) . . ?
H19A C19A H20C 81.8 . . ?
H19B C19A H20C 100.8 . . ?
C18 C21A H21A 109.5 . . ?
C18 C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
C18 C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C18 C22A H22A 109.5 . . ?
C18 C22A H22B 109.5 . . ?
H22A C22A H22B 109.5 . . ?
C18 C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.041
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelxl_6626
_database_code_depnum_ccdc_archive 'CCDC 1030236'

_audit_update_record             
;
2014-10-20 deposited with the CCDC.
2015-04-24 downloaded from the CCDC.
;
_audit_creation_method           'manual editing of SHELXL97.CIF'

#=====================================================================

_chemical_name_systematic        
;
Selective Endocytic Trafficking in Live Cells with Fluorescent Oxazoles 
and their Boron Complexes.

;

_chemical_formula_sum            'C22 H18 B F2 N O3'
_chemical_formula_weight         392.18
_cell_length_a                   8.671(2)
_cell_length_b                   10.289(2)
_cell_length_c                   11.776(2)
_cell_angle_alpha                70.09(3)
_cell_angle_beta                 88.30(2)
_cell_angle_gamma                68.38(3)
_cell_volume                     912.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_exptl_crystal_density_diffrn    1.427
_refine_ls_R_factor_gt           0.0505


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.33872(17) -0.28952(13) 0.46643(13) 0.0494(4) Uani 1 1 d . . .
O2 O 0.15498(13) 0.14204(12) 0.45474(9) 0.0282(3) Uani 1 1 d . . .
O3 O -0.26858(13) 0.56401(11) 0.15323(10) 0.0283(3) Uani 1 1 d . . .
N1 N 0.15074(16) -0.02420(14) 0.37656(11) 0.0267(3) Uani 1 1 d . . .
F2 F 0.08173(13) -0.22726(11) 0.36802(10) 0.0449(3) Uani 1 1 d . . .
F1 F 0.27961(14) -0.17369(12) 0.25689(10) 0.0521(3) Uani 1 1 d . . .
B1 B 0.2145(2) -0.1846(2) 0.36573(18) 0.0327(4) Uani 1 1 d . . .
C1 C 0.4040(2) -0.25886(19) 0.55052(16) 0.0358(4) Uani 1 1 d . . .
C2 C 0.5314(2) -0.3736(2) 0.63813(18) 0.0463(5) Uani 1 1 d . . .
H2 H 0.5708 -0.4704 0.6373 0.056 Uiso 1 1 calc R . .
C3 C 0.5977(2) -0.3430(2) 0.72501(17) 0.0477(5) Uani 1 1 d . . .
H3 H 0.6827 -0.4200 0.7826 0.057 Uiso 1 1 calc R . .
C4 C 0.5420(2) -0.2003(2) 0.72981(17) 0.0443(5) Uani 1 1 d . . .
H4 H 0.5885 -0.1824 0.7903 0.053 Uiso 1 1 calc R . .
C5 C 0.4172(2) -0.0855(2) 0.64429(15) 0.0371(4) Uani 1 1 d . . .
H5 H 0.3790 0.0107 0.6464 0.045 Uiso 1 1 calc R . .
C6 C 0.34817(19) -0.11424(18) 0.55448(14) 0.0299(4) Uani 1 1 d . . .
C7 C 0.21852(19) -0.00115(17) 0.46239(14) 0.0276(3) Uani 1 1 d . . .
C8 C 0.03567(18) 0.21639(17) 0.35395(13) 0.0253(3) Uani 1 1 d . . .
C9 C 0.03150(18) 0.11540(16) 0.30432(14) 0.0245(3) Uani 1 1 d . . .
C10 C -0.07922(18) 0.16311(16) 0.19897(13) 0.0236(3) Uani 1 1 d . . .
C11 C -0.0951(2) 0.07071(17) 0.13832(14) 0.0278(3) Uani 1 1 d . . .
H11 H -0.0303 -0.0312 0.1683 0.033 Uiso 1 1 calc R . .
C12 C -0.2049(2) 0.12994(18) 0.03584(15) 0.0306(4) Uani 1 1 d . . .
H12 H -0.2142 0.0679 -0.0031 0.037 Uiso 1 1 calc R . .
C13 C -0.3032(2) 0.28281(18) -0.01079(15) 0.0303(4) Uani 1 1 d . . .
H13 H -0.3775 0.3218 -0.0804 0.036 Uiso 1 1 calc R . .
C14 C -0.29045(19) 0.37516(17) 0.04544(14) 0.0272(3) Uani 1 1 d . . .
H14 H -0.3561 0.4768 0.0133 0.033 Uiso 1 1 calc R . .
C15 C -0.17924(18) 0.31892(16) 0.15149(13) 0.0233(3) Uani 1 1 d . . .
C16 C -0.16678(18) 0.41807(16) 0.20868(14) 0.0242(3) Uani 1 1 d . . .
C17 C -0.06017(19) 0.36949(16) 0.31186(14) 0.0253(3) Uani 1 1 d . . .
C18 C -0.0507(2) 0.47223(17) 0.37358(15) 0.0311(4) Uani 1 1 d . . .
H18A H 0.0544 0.4858 0.3622 0.037 Uiso 1 1 calc R . .
H18B H -0.0554 0.4286 0.4601 0.037 Uiso 1 1 calc R . .
C19 C -0.1948(2) 0.62264(17) 0.32100(15) 0.0309(4) Uani 1 1 d . . .
H19A H -0.1710 0.6966 0.3429 0.037 Uiso 1 1 calc R . .
H19B H -0.2955 0.6151 0.3556 0.037 Uiso 1 1 calc R . .
C20 C -0.22380(19) 0.67349(17) 0.18345(15) 0.0281(3) Uani 1 1 d . . .
C21 C -0.3737(2) 0.81864(18) 0.13067(18) 0.0380(4) Uani 1 1 d . . .
H21A H -0.3954 0.8413 0.0452 0.057 Uiso 1 1 calc R . .
H21B H -0.3515 0.8979 0.1431 0.057 Uiso 1 1 calc R . .
H21C H -0.4693 0.8088 0.1703 0.057 Uiso 1 1 calc R . .
C22 C -0.0701(2) 0.68372(19) 0.12167(17) 0.0372(4) Uani 1 1 d . . .
H22A H 0.0170 0.5859 0.1454 0.056 Uiso 1 1 calc R . .
H22B H -0.0328 0.7486 0.1455 0.056 Uiso 1 1 calc R . .
H22C H -0.0974 0.7231 0.0351 0.056 Uiso 1 1 calc R . .


_geom_special_details            
; 
 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. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.334(2) . ?
O1 B1 1.442(2) . ?
O2 C7 1.3404(18) . ?
O2 C8 1.3912(17) . ?
O3 C16 1.3601(17) . ?
O3 C20 1.4662(18) . ?
N1 C7 1.313(2) . ?
N1 C9 1.4076(19) . ?
N1 B1 1.585(2) . ?
F2 B1 1.372(2) . ?
F1 B1 1.371(2) . ?
C1 C2 1.398(2) . ?
C1 C6 1.402(2) . ?
C2 C3 1.366(3) . ?
C3 C4 1.387(3) . ?
C4 C5 1.376(2) . ?
C5 C6 1.395(2) . ?
C6 C7 1.429(2) . ?
C8 C9 1.366(2) . ?
C8 C17 1.395(2) . ?
C9 C10 1.418(2) . ?
C10 C11 1.413(2) . ?
C10 C15 1.424(2) . ?
C11 C12 1.369(2) . ?
C12 C13 1.398(2) . ?
C13 C14 1.365(2) . ?
C14 C15 1.412(2) . ?
C15 C16 1.435(2) . ?
C16 C17 1.376(2) . ?
C17 C18 1.498(2) . ?
C18 C19 1.519(2) . ?
C19 C20 1.520(2) . ?
C20 C21 1.514(2) . ?
C20 C22 1.520(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 B1 127.05(14) . . ?
C7 O2 C8 105.25(11) . . ?
C16 O3 C20 116.17(11) . . ?
C7 N1 C9 106.54(13) . . ?
C7 N1 B1 120.88(13) . . ?
C9 N1 B1 132.48(13) . . ?
F1 B1 F2 109.76(16) . . ?
F1 B1 O1 111.30(15) . . ?
F2 B1 O1 110.03(15) . . ?
F1 B1 N1 107.74(14) . . ?
F2 B1 N1 108.88(14) . . ?
O1 B1 N1 109.07(14) . . ?
O1 C1 C2 119.54(17) . . ?
O1 C1 C6 121.93(15) . . ?
C2 C1 C6 118.53(18) . . ?
C3 C2 C1 119.76(19) . . ?
C2 C3 C4 121.90(17) . . ?
C5 C4 C3 119.37(19) . . ?
C4 C5 C6 119.64(18) . . ?
C5 C6 C1 120.79(15) . . ?
C5 C6 C7 123.02(16) . . ?
C1 C6 C7 116.19(15) . . ?
N1 C7 O2 112.98(13) . . ?
N1 C7 C6 124.64(15) . . ?
O2 C7 C6 122.38(14) . . ?
C9 C8 O2 108.69(13) . . ?
C9 C8 C17 126.87(14) . . ?
O2 C8 C17 124.43(13) . . ?
C8 C9 N1 106.54(13) . . ?
C8 C9 C10 120.06(13) . . ?
N1 C9 C10 133.39(14) . . ?
C11 C10 C9 125.74(14) . . ?
C11 C10 C15 118.85(13) . . ?
C9 C10 C15 115.40(13) . . ?
C12 C11 C10 120.56(14) . . ?
C11 C12 C13 120.64(15) . . ?
C14 C13 C12 120.24(14) . . ?
C13 C14 C15 121.06(14) . . ?
C14 C15 C10 118.65(13) . . ?
C14 C15 C16 120.20(13) . . ?
C10 C15 C16 121.15(13) . . ?
O3 C16 C17 122.41(13) . . ?
O3 C16 C15 114.92(13) . . ?
C17 C16 C15 122.66(13) . . ?
C16 C17 C8 113.84(13) . . ?
C16 C17 C18 122.67(13) . . ?
C8 C17 C18 123.49(13) . . ?
C17 C18 C19 109.90(13) . . ?
C18 C19 C20 111.40(13) . . ?
O3 C20 C21 104.40(12) . . ?
O3 C20 C22 107.89(13) . . ?
C21 C20 C22 111.12(14) . . ?
O3 C20 C19 108.12(12) . . ?
C21 C20 C19 111.90(14) . . ?
C22 C20 C19 112.92(14) . . ?

_diffrn_measured_fraction_theta_max 0.865
_diffrn_reflns_theta_full        29.90
_diffrn_measured_fraction_theta_full 0.865
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.046

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ENSJ187
_database_code_depnum_ccdc_archive 'CCDC 1030237'

_audit_update_record             
;
2014-10-20 deposited with the CCDC.
2015-04-24 downloaded from the CCDC.
;
_audit_creation_method           'manual editing of SHELXL97.CIF'

#=====================================================================

_chemical_name_systematic        
;
Selective Endocytic Trafficking in Live Cells with Fluorescent Oxazoles 
and their Boron Complexes.

;
_chemical_formula_sum            'C21 H16 B F2 N O3'
_chemical_formula_weight         378.15
_cell_length_a                   13.1650(4)
_cell_length_b                   7.1780(7)
_cell_length_c                   17.9760(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1698.70(2)
_symmetry_space_group_name_H-M   'P n m a'
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_exptl_crystal_density_diffrn    1.476
_refine_ls_R_factor_gt           0.066


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F F 0.94872(13) 0.0935(3) 0.34000(9) 0.0517(5) Uani 1 1 d . . .
O1 O 1.3739(2) 0.2500 0.57361(14) 0.0421(8) Uani 1 2 d S . .
O2 O 1.01362(18) 0.2500 0.57679(13) 0.0307(6) Uani 1 2 d S . .
C9 C 1.2015(3) 0.2500 0.58132(19) 0.0299(9) Uani 1 2 d S . .
N N 0.9925(2) 0.2500 0.45456(16) 0.0278(7) Uani 1 2 d S . .
C10 C 1.1084(3) 0.2500 0.54462(19) 0.0274(8) Uani 1 2 d S . .
C11 C 0.9471(3) 0.2500 0.52002(19) 0.0284(8) Uani 1 2 d S . .
O3 O 0.8178(2) 0.2500 0.40016(15) 0.0440(8) Uani 1 2 d S . .
C16 C 0.6738(3) 0.2500 0.4787(2) 0.0385(10) Uani 1 2 d S . .
H16 H 0.6311 0.2500 0.4375 0.046 Uiso 1 2 calc SR . .
C2 C 1.1846(3) 0.2500 0.42055(19) 0.0281(8) Uani 1 2 d S . .
C17 C 0.7784(3) 0.2500 0.4686(2) 0.0305(9) Uani 1 2 d S . .
C1 C 1.0975(3) 0.2500 0.46853(19) 0.0280(8) Uani 1 2 d S . .
C12 C 0.8403(3) 0.2500 0.5322(2) 0.0298(9) Uani 1 2 d S . .
C4 C 1.2695(3) 0.2500 0.3019(2) 0.0363(10) Uani 1 2 d S . .
H4 H 1.2662 0.2500 0.2502 0.044 Uiso 1 2 calc SR . .
C14 C 0.6942(3) 0.2500 0.6116(2) 0.0429(11) Uani 1 2 d S . .
H14 H 0.6652 0.2500 0.6587 0.052 Uiso 1 2 calc SR . .
C3 C 1.1814(3) 0.2500 0.34232(19) 0.0319(9) Uani 1 2 d S . .
H3 H 1.1190 0.2500 0.3180 0.038 Uiso 1 2 calc SR . .
C8 C 1.2844(3) 0.2500 0.5363(2) 0.0303(9) Uani 1 2 d S . .
C7 C 1.2816(3) 0.2500 0.4566(2) 0.0302(9) Uani 1 2 d S . .
C6 C 1.3695(3) 0.2500 0.4129(2) 0.0355(9) Uani 1 2 d S . .
H6 H 1.4327 0.2500 0.4360 0.043 Uiso 1 2 calc SR . .
C5 C 1.3647(3) 0.2500 0.3371(2) 0.0369(10) Uani 1 2 d S . .
H5 H 1.4240 0.2500 0.3089 0.044 Uiso 1 2 calc SR . .
C13 C 0.7976(3) 0.2500 0.6034(2) 0.0364(10) Uani 1 2 d S . .
H13 H 0.8393 0.2500 0.6452 0.044 Uiso 1 2 calc SR . .
C19 C 1.3518(3) 0.2500 0.65463(19) 0.0337(9) Uani 1 2 d S . .
C18 C 1.2342(3) 0.2500 0.6610(2) 0.0424(11) Uani 1 2 d S . .
H18A H 1.2100 0.1399 0.6867 0.051 Uiso 0.50 1 calc PR . .
H18B H 1.2100 0.3601 0.6867 0.051 Uiso 0.50 1 calc PR . .
C20 C 1.3995(2) 0.4230(5) 0.68580(17) 0.0513(9) Uani 1 1 d . . .
H20A H 1.3670 0.5307 0.6649 0.077 Uiso 1 1 calc R . .
H20B H 1.4705 0.4249 0.6736 0.077 Uiso 1 1 calc R . .
H20C H 1.3916 0.4243 0.7389 0.077 Uiso 1 1 calc R . .
C15 C 0.6330(3) 0.2500 0.5486(2) 0.0435(11) Uani 1 2 d S . .
H15 H 0.5627 0.2500 0.5541 0.052 Uiso 1 2 calc SR . .
B B 0.9253(4) 0.2500 0.3802(2) 0.0369(11) Uani 1 2 d S . .


_geom_special_details            
;
 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.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F B 1.371(3) . ?
O1 C8 1.356(4) . ?
O1 C19 1.485(4) . ?
O2 C11 1.345(4) . ?
O2 C10 1.376(4) . ?
C9 C8 1.359(5) . ?
C9 C10 1.391(5) . ?
C9 C18 1.495(5) . ?
N C11 1.320(4) . ?
N C1 1.405(5) . ?
N B 1.602(5) . ?
C10 C1 1.375(5) . ?
C11 C12 1.423(5) . ?
O3 C17 1.335(5) . ?
O3 B 1.460(5) . ?
C16 C15 1.367(6) . ?
C16 C17 1.388(5) . ?
C16 H16 0.9300 . ?
C2 C3 1.407(5) . ?
C2 C7 1.432(5) . ?
C2 C1 1.435(5) . ?
C17 C12 1.405(5) . ?
C12 C13 1.398(5) . ?
C4 C3 1.369(5) . ?
C4 C5 1.405(6) . ?
C4 H4 0.9300 . ?
C14 C13 1.369(5) . ?
C14 C15 1.389(6) . ?
C14 H14 0.9300 . ?
C3 H3 0.9300 . ?
C8 C7 1.433(5) . ?
C7 C6 1.400(5) . ?
C6 C5 1.364(5) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
C13 H13 0.9300 . ?
C19 C20 1.500(4) . ?
C19 C20 1.500(4) 8_565 ?
C19 C18 1.552(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C15 H15 0.9300 . ?
B F 1.371(3) 8_565 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C19 108.3(3) . . ?
C11 O2 C10 105.8(3) . . ?
C8 C9 C10 115.2(3) . . ?
C8 C9 C18 109.8(3) . . ?
C10 C9 C18 135.1(3) . . ?
C11 N C1 106.6(3) . . ?
C11 N B 119.6(3) . . ?
C1 N B 133.8(3) . . ?
C1 C10 O2 108.9(3) . . ?
C1 C10 C9 124.3(3) . . ?
O2 C10 C9 126.8(3) . . ?
N C11 O2 112.4(3) . . ?
N C11 C12 125.8(3) . . ?
O2 C11 C12 121.8(3) . . ?
C17 O3 B 127.1(3) . . ?
C15 C16 C17 120.7(4) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C3 C2 C7 118.7(3) . . ?
C3 C2 C1 125.2(3) . . ?
C7 C2 C1 116.2(3) . . ?
O3 C17 C16 120.4(3) . . ?
O3 C17 C12 121.6(3) . . ?
C16 C17 C12 118.0(4) . . ?
C10 C1 N 106.3(3) . . ?
C10 C1 C2 120.9(3) . . ?
N C1 C2 132.8(3) . . ?
C13 C12 C17 120.8(4) . . ?
C13 C12 C11 122.6(3) . . ?
C17 C12 C11 116.6(3) . . ?
C3 C4 C5 121.2(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C13 C14 C15 119.4(4) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C4 C3 C2 120.3(4) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
O1 C8 C9 113.8(3) . . ?
O1 C8 C7 121.1(3) . . ?
C9 C8 C7 125.1(3) . . ?
C6 C7 C2 118.9(3) . . ?
C6 C7 C8 122.7(3) . . ?
C2 C7 C8 118.4(3) . . ?
C5 C6 C7 121.5(4) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C5 C4 119.4(4) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C14 C13 C12 119.8(4) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
O1 C19 C20 106.5(2) . . ?
O1 C19 C20 106.5(2) . 8_565 ?
C20 C19 C20 111.7(4) . 8_565 ?
O1 C19 C18 105.5(3) . . ?
C20 C19 C18 113.0(2) . . ?
C20 C19 C18 113.0(2) 8_565 . ?
C9 C18 C19 102.6(3) . . ?
C9 C18 H18A 111.3 . . ?
C19 C18 H18A 111.3 . . ?
C9 C18 H18B 111.3 . . ?
C19 C18 H18B 111.3 . . ?
H18A C18 H18B 109.2 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C15 C14 121.4(4) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
F B F 110.0(3) . 8_565 ?
F B O3 110.3(2) . . ?
F B O3 110.3(2) 8_565 . ?
F B N 108.4(2) . . ?
F B N 108.4(2) 8_565 . ?
O3 B N 109.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.061
