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_7708683
_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
'C50 H42 Cu N2 O P2, B F4, 1[C1H2Cl2], 1[C4H10O1]'
_chemical_formula_sum            'C55 H54 B Cl2 Cu F4 N2 O2 P2'
_chemical_formula_weight         1058.19
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-02-17
_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                109.7369(15)
_cell_angle_beta                 93.2992(17)
_cell_angle_gamma                110.6852(16)
_cell_formula_units_Z            2
_cell_length_a                   10.8320(5)
_cell_length_b                   14.9163(6)
_cell_length_c                   18.2441(8)
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    150
_cell_measurement_theta_max      70.337
_cell_measurement_theta_min      3.429
_cell_volume                     2542.8(2)
_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)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            33057
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.256
_diffrn_reflns_theta_min         2.626
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.649
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0743 before and 0.0382 after correction.
The Ratio of minimum to maximum transmission is 0.8576.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of DCM and Et2O  by solvent layering'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.213
_refine_diff_density_min         -1.552
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     547
_refine_ls_number_reflns         9409
_refine_ls_number_restraints     85
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0610
_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^)+(0.1031P)^2^+4.0797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1758
_refine_ls_wR_factor_ref         0.1805
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8707
_reflns_number_total             9409
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt03239a2.cif
_cod_data_source_block           mem041_150k_0m
_cod_original_cell_volume        2542.84(19)
_cod_database_code               7708683
_shelx_shelxl_version_number     2018/3
_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
 F1-F2 \\sim F1-F3 \\sim F1-F4 \\sim F2-F3 \\sim F3-F4
 with sigma of 0.01
 B1-F1 \\sim B1-F2 \\sim B1-F3 \\sim B1-F4
 with sigma of 0.005
 F5-F6 \\sim F5-F7 \\sim F5-F8 \\sim F6-F7 \\sim F6-F8 \\sim F7-F8
 with sigma of 0.01
 B1-F5 \\sim B1-F6 \\sim B1-F7 \\sim B1-F8
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F4) \\sim
Ueq, Uanis(F5) \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F7) \\sim Ueq, Uanis(F8)
\\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(F1) = Uanis(F2) = Uanis(F3) = Uanis(F4) = Uanis(F5) = Uanis(F6) =
Uanis(F7) = Uanis(F8)
4. Others
 Fixed Sof: F1(0.5) F2(0.5) F3(0.5) F4(0.5) F5(0.5) F6(0.5) F7(0.5) F8(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C25(H25), C40(H40), C34(H34), C27(H27), C46(H46), C41(H41), C50(H50),
 C36(H36), C19(H19), C11(H11), C35(H35), C44(H44), C42(H42), C26(H26), C49(H49),
  C43(H43), C13(H13), C47(H47), C48(H48), C23(H23), C20(H20), C16(H16),
 C14(H14), C17(H17), C8(H8), C5(H5), C22(H22), C21(H21), C3(H3), C15(H15),
 C10(H10), C9(H9), C4(H4)
5.b Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C1(H1A,H1B,H1C), C37(H37A,H37B,H37C)
;
_shelx_res_checksum              59603
_shelx_hkl_checksum              23255
_shelx_fab_checksum              73288
_olex2_date_sample_data_collection 2020-02-15
_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 MEM041_150K
_olex2_submission_special_instructions 'No special instructions were received'