Utility of tris(4-bromopyridyl) europium complexes as versatile intermediates in the divergent synthesis of emissive chiral probes.
Butler, Stephen J.; Delbianco, Martina; Evans, Nicholas H.; Frawley, Andrew T.; Pal, Robert; Parker, David; Puckrin, Robert S.; Yufit, Dmitry S.; Dalton transactions (Cambridge, England : 2003) 43 (2014) 5721–5730; doi:10.1039/c4dt00253a

data_7029447
_publ_section_title
;
 Utility of tris(4-bromopyridyl) europium complexes as versatile
 intermediates in the divergent synthesis of emissive chiral probes.
;
_journal_issue                   15
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5721
_journal_page_last               5730
_journal_paper_doi               10.1039/c4dt00253a
_journal_volume                  43
_journal_year                    2014
_chemical_formula_moiety         'C54 H57 Eu N15 O9 P3, 2(H2 O)'
_chemical_formula_sum            'C54 H61 Eu N15 O11 P3'
_chemical_formula_weight         1341.05
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-07-10
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.310(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   59.156(4)
_cell_length_b                   13.3370(10)
_cell_length_c                   18.5660(10)
_cell_measurement_reflns_used    8294
_cell_measurement_temperature    100
_cell_measurement_theta_max      21.57
_cell_measurement_theta_min      2.26
_cell_volume                     14311.1(16)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Rigaku CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'Bruker APEX2'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 0.0350
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       ' 'CrystalLogic Kappa (4 circle)'
_diffrn_measurement_device_type  'Kappa Rigaku Saturn724+'
_diffrn_measurement_method       'omega rotation'
_diffrn_radiation_collimation    '0.3 x 1.5 Double Pinhole'
_diffrn_radiation_monochromator  Synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.688900
_diffrn_reflns_av_R_equivalents  0.0892
_diffrn_reflns_av_unetI/netI     0.0753
_diffrn_reflns_limit_h_max       70
_diffrn_reflns_limit_h_min       -70
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            56723
_diffrn_reflns_theta_full        23.50
_diffrn_reflns_theta_max         24.29
_diffrn_reflns_theta_min         0.68
_diffrn_source                   Synchrotron
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.926
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0730 before and 0.0571 after correction.
The Ratio of minimum to maximum transmission is 0.8701.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             5488
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.869
_refine_diff_density_min         -0.774
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     725
_refine_ls_number_reflns         11499
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1309
_reflns_number_gt                7477
_reflns_number_total             11499
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4dt00253a2.cif
_cod_data_source_block           ne201
_cod_database_code               7029447
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
O3A \\sim O3: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
N5 \\sim N5A: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
C22 \\sim C22A: within 1.7A with sigma of 0.005 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: O3(0.5) O3A(0.5) N5(0.5) N5A(0.5) N6(0.5) N6A(0.5) N7(0.5)
 N7A(0.5) C14(0.5) H14(0.5) C14A(0.5) H14A(0.5) C15(0.5) C15A(0.5) C16(0.5)
 C21(0.5) H21(0.5) C20(0.5) H20(0.5) C19(0.5) C18(0.5) H18(0.5) C17(0.5)
 H17(0.5) C16A(0.5) C21A(0.5) H21A(0.5) C20A(0.5) H20A(0.5) C19A(0.5) C18A(0.5)
 H18A(0.5) C17A(0.5) H17A(0.5) C22(0.5) H22A(0.5) H22B(0.5) H22C(0.5) C22A(0.5)
 H22D(0.5) H22E(0.5) H22F(0.5)
4.a Riding coordinates:
 C22(H22A,H22B,H22C), C22A(H22D,H22E,H22F), O1W(H1WA,H1WB), O2W(H2WA,H2WB)
4.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C23(H23A,H23B), C39(H39A,H39B)
4.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C14(H14), C14A(H14A), C21(H21), C20(H20), C18(H18),
 C17(H17), C21A(H21A), C20A(H20A), C18A(H18A), C17A(H17A), C25(H25), C27(H27),
 C30(H30), C33(H33), C34(H34), C36(H36), C37(H37), C41(H41), C43(H43), C46(H46),
  C49(H49), C50(H50), C52(H52), C53(H53)
4.d Fitted hexagon refined as free rotating group:
 C16(C21,C20,C19,C18,C17), C16A(C21A,C20A,C19A,C18A,C17A)
4.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C29(H29A,H29B,H29C), C38(H38A,H38B,H38C), C45(H45A,H45B,
 H45C), C54(H54A,H54B,H54C)
;