A counterion study of a series of [Cu(P^P)(N^N)][A] compounds with bis(phosphane) and 6-methyl and 6,6'-dimethyl-substituted 2,2'-bipyridine ligands for light-emitting electrochemical cells
Meyer, Marco; Mardegan, Lorenzo; Tordera, Daniel; Prescimone, Alessandro; Sessolo, Michele; Bolink, Henk J.; Constable, Edwin C.; Housecroft, Catherine E.; Dalton Transactions  (2021) –; doi:10.1039/D1DT03239A

data_7708684
_publ_section_title
;
 A counterion study of a series of [Cu(P^P)(N^N)][A] compounds with
 bis(phosphane) and 6-methyl and 6,6'-dimethyl-substituted 2,2'-bipyridine
 ligands for light-emitting electrochemical cells
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D1DT03239A
_journal_year                    2021
_chemical_formula_moiety         'C48 H40 Cu N2 O P2, C32 H12 B F24'
_chemical_formula_sum            'C80 H52 B Cu F24 N2 O P2'
_chemical_formula_weight         1649.52
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-02-21
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-05-01 deposited with the CCDC.	2021-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                89.276(3)
_cell_angle_beta                 76.079(3)
_cell_angle_gamma                85.590(3)
_cell_formula_units_Z            2
_cell_length_a                   13.4775(10)
_cell_length_b                   13.7430(11)
_cell_length_c                   20.8898(16)
_cell_measurement_reflns_used    3811
_cell_measurement_temperature    150
_cell_measurement_theta_max      69.013
_cell_measurement_theta_min      3.902
_cell_volume                     3744.4(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            34371
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.381
_diffrn_reflns_theta_min         2.179
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.768
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0859 before and 0.0364 after correction.
The Ratio of minimum to maximum transmission is 0.8720.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_description       block
_exptl_crystal_F_000             1668
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of acetone and cyclohexane  by solvent layering'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.715
_refine_diff_density_min         -0.998
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1002
_refine_ls_number_reflns         13675
_refine_ls_number_restraints     112
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0633
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0805P)^2^+8.2490P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1633
_refine_ls_wR_factor_ref         0.1692
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12292
_reflns_number_total             13675
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt03239a2.cif
_cod_data_source_block           mem066_150k_0m
_cod_database_code               7708684
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.816
_shelx_estimated_absorpt_t_min   0.719
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C75-F22 \\sim C75-F23 \\sim C75-F24 \\sim F22-F23 \\sim F22-F24 \\sim F23-F24
 with sigma of 0.04
 C80-C75 \\sim C80-F22 \\sim C80-F23 \\sim C80-F24
 with sigma of 0.02
 F16-F17 \\sim F16-F19 \\sim F17-F19
 with sigma of 0.04
 C71-F16 \\sim C71-C69 \\sim C71-F17 \\sim C71-F19
 with sigma of 0.02
 C61-F18 \\sim C61-F20 \\sim C61-F21 \\sim F18-F20 \\sim F18-F21 \\sim F20-F21
 with sigma of 0.04
 C63-C61 \\sim C63-F18 \\sim C63-F20 \\sim C63-F21
 with sigma of 0.02
 F25-F26 \\sim F25-F27 \\sim F26-F27
 with sigma of 0.04
 C80-C75 \\sim C80-F25 \\sim C80-F26 \\sim C80-F27
 with sigma of 0.02
 F28-F29 \\sim F28-F30 \\sim F29-F30
 with sigma of 0.04
 C71-C69 \\sim C71-F28 \\sim C71-F29 \\sim C71-F30
 with sigma of 0.02
 F31-F32 \\sim F31-F33 \\sim F32-F33
 with sigma of 0.04
 C63-C61 \\sim C63-F31 \\sim C63-F32 \\sim C63-F33
 with sigma of 0.02
 F1-C63 \\sim F2-C63
 with sigma of 0.02
 F0AA-F2 \\sim F1AA-F1 \\sim F0AA-F2 \\sim F1AA-F1
 with sigma of 0.02
 F3-C63 \\sim F1-C63 \\sim F2-C63
 with sigma of 0.02
 F1-F2 \\sim F1-F3 \\sim F2-F3
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F22) = Uanis(F23) = Uanis(F24) = Uanis(F25) = Uanis(F26) = Uanis(F27)
Uanis(F16) = Uanis(F17) = Uanis(F19) = Uanis(F28) = Uanis(F29) = Uanis(F30)
Uanis(F18) = Uanis(F20) = Uanis(F21) = Uanis(F31) = Uanis(F32) = Uanis(F33)
Uanis(F18) = Uanis(F20) = Uanis(F21) = Uanis(F31) = Uanis(F32) = Uanis(F33) =
Uanis(F2) = Uanis(F1) = Uanis(F3)
4. Others
 Fixed Sof: F16(0.5) F17(0.5) F18(0.33333) F19(0.5) F20(0.33333) F21(0.33333)
 F22(0.5) F23(0.5) F24(0.5) F25(0.5) F26(0.5) F27(0.5) F28(0.5) F29(0.5)
 F30(0.5) F31(0.33333) F32(0.33333) F33(0.33333) F2(0.33333) F1(0.33333)
 F3(0.33333)
5.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C50(H50), C74(H74), C54(H54), C78(H78), C66(H66), C18(H18),
 C58(H58), C3(H3), C70(H70), C30(H30), C62(H62), C38(H38), C52(H52), C44(H44),
 C60(H60), C76(H76), C36(H36), C42(H42), C27(H27), C20(H20), C15(H15), C24(H24),
  C17(H17), C5(H5), C16(H16), C4(H4), C33(H33), C29(H29), C23(H23), C48(H48),
 C34(H34), C21(H21), C45(H45), C39(H39), C40(H40), C35(H35), C68(H68), C46(H46),
  C28(H28), C22(H22), C41(H41), C10(H10), C8(H8), C47(H47), C9(H9)
5.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              83673
_shelx_hkl_checksum              3133
_olex2_date_sample_data_collection 2020-02-20
_olex2_date_sample_submission    2020-01-24
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a mylar loop in perfluoroether oil'
_olex2_submission_original_sample_id MEM066_150K
_olex2_submission_special_instructions 'No special instructions were received'