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_7708681
_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
'C51 H44 Cu N2 O P2, B F4, 0.5(C6 H12), 0.8[C3H6O1]'
_chemical_formula_sum            'C56.4 H54.8 B Cu F4 N2 O1.8 P2'
_chemical_formula_weight         1001.71
_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     dual
_audit_creation_date             2020-02-20
_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                67.326(3)
_cell_angle_beta                 77.613(3)
_cell_angle_gamma                85.130(3)
_cell_formula_units_Z            2
_cell_length_a                   11.0536(7)
_cell_length_b                   14.3637(9)
_cell_length_c                   18.0991(12)
_cell_measurement_reflns_used    9351
_cell_measurement_temperature    150
_cell_measurement_theta_max      69.986
_cell_measurement_theta_min      3.408
_cell_volume                     2589.8(3)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \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  0.0277
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            27941
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.199
_diffrn_reflns_theta_min         3.334
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.642
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0536 before and 0.0368 after correction.
The Ratio of minimum to maximum transmission is 0.9104.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       block
_exptl_crystal_F_000             1043
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of acetone and cyclohexane  by solvent layering'
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_refine_diff_density_max         2.280
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     587
_refine_ls_number_reflns         9439
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0583
_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^)+(0.1162P)^2^+3.3624P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1805
_refine_ls_wR_factor_ref         0.1842
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8700
_reflns_number_total             9439
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt03239a2.cif
_cod_data_source_block           mem043_150k_0m
_cod_original_formula_sum        'C56.40 H54.80 B Cu F4 N2 O1.80 P2'
_cod_database_code               7708681
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.894
_shelx_estimated_absorpt_t_min   0.840
_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
2. Restrained distances
 C55-C56 \\sim C57-C56 \\sim C57-C52 \\sim C53-C52 \\sim C53-C54 \\sim C55-C54
 with sigma of 0.02
 F1-F2 \\sim F1-F3 \\sim F1-F4 \\sim F2-F3 \\sim F2-F4 \\sim F3-F4
 with sigma of 0.04
 B1-F1 \\sim B1-F2 \\sim B1-F3 \\sim B1-F4
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C57) = Uanis(C52) = Uanis(C53) = Uanis(C54) = Uanis(C55) = Uanis(C56)
4. Others
 Fixed Sof: C55(0.5) H55A(0.5) H55B(0.5) C53(0.5) H53A(0.5) H53B(0.5) C57(0.5)
 H57A(0.5) H57B(0.5) C56(0.5) H56A(0.5) H56B(0.5) C52(0.5) H52A(0.5) H52B(0.5)
 C54(0.5) H54A(0.5) H54B(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C55(H55A,H55B), C53(H53A,H53B), C57(H57A,H57B), C56(H56A,H56B), C52(H52A,
 H52B), C54(H54A,H54B)
5.b Aromatic/amide H refined with riding coordinates:
 C28(H28), C30(H30), C14(H14), C35(H35), C29(H29), C18(H18), C10(H10),
 C21(H21), C20(H20), C16(H16), C17(H17), C22(H22), C15(H15), C47(H47), C24(H24),
  C9(H9), C36(H36), C37(H37), C5(H5), C41(H41), C8(H8), C23(H23), C3(H3),
 C51(H51), C45(H45), C4(H4), C48(H48), C42(H42), C43(H43), C49(H49), C50(H50),
 C44(H44)
5.c Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C12(H12A,H12B,H12C), C38(H38A,H38B,H38C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              68572
_shelx_hkl_checksum              76524
_shelx_fab_checksum              63378
_olex2_date_sample_data_collection 2020-02-19
_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 MEM043_150K
_olex2_submission_special_instructions 'No special instructions were received'