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_7708687
_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         'C47 H38 Cu N2 O P2, C32 H12 B F24, C6 H12'
_chemical_formula_sum            'C85 H62 B Cu F24 N2 O P2'
_chemical_formula_weight         1719.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-05-01 deposited with the CCDC.	2021-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.048(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2327(4)
_cell_length_b                   30.8018(9)
_cell_length_c                   18.4314(5)
_cell_measurement_reflns_used    9644
_cell_measurement_temperature    150
_cell_measurement_theta_max      69.596
_cell_measurement_theta_min      4.811
_cell_volume                     8060.0(4)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.947
_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           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            58689
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.110
_diffrn_reflns_theta_min         2.799
_diffrn_source_current           0.6
_diffrn_source_power             0.03
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.665
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1091 before and 0.0479 after correction.
The Ratio of minimum to maximum transmission is 0.8903.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       plate
_exptl_crystal_F_000             3496
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.617
_refine_diff_density_min         -1.120
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     962
_refine_ls_number_reflns         14521
_refine_ls_number_restraints     95
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0865
_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^)+(0.0788P)^2^+30.6555P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2089
_refine_ls_wR_factor_ref         0.2156
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12748
_reflns_number_total             14521
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt03239a2.cif
_cod_data_source_block           mem067_150k_0m
_cod_database_code               7708687
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.921
_shelx_estimated_absorpt_t_min   0.711
_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
 C75-C73 \\sim C75-F3 \\sim C75-F25 \\sim C75-F13
 with sigma of 0.02
 F3-F25 \\sim F3-F13 \\sim F25-F13
 with sigma of 0.04
 C75-F29 \\sim C75-F30 \\sim C75-F28 \\sim C75-C73
 with sigma of 0.02
 F29-F30 \\sim F29-F28 \\sim F30-F28
 with sigma of 0.04
 F21-F7 \\sim F21-F23 \\sim F7-F23
 with sigma of 0.04
 C59-F21 \\sim C59-F7 \\sim C59-F23 \\sim C59-C57
 with sigma of 0.02
 C85-C57 \\sim C85-F31 \\sim C85-F32 \\sim C85-F33
 with sigma of 0.02
 F31-F32 \\sim F32-F33
 with sigma of 0.04
 C85-C57 \\sim C59-C57
 with sigma of 0.02
 F14-F2 \\sim F14-F5 \\sim F2-F5
 with sigma of 0.04
 C76-F14 \\sim C76-F2 \\sim C76-C71 \\sim C76-F5
 with sigma of 0.02
 C76-F35 \\sim C76-F36 \\sim C76-F34 \\sim C76-C71
 with sigma of 0.02
 F35-F36 \\sim F35-F34 \\sim F36-F34
 with sigma of 0.04
 F11-F15 \\sim F11-F17 \\sim F15-F17
 with sigma of 0.04
 C60-F11 \\sim C60-F15 \\sim C60-C55 \\sim C60-F17
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(N1) = Uanis(C5) = Uanis(C4) = Uanis(C3) = Uanis(C2) = Uanis(C1) =
Uanis(N3) = Uanis(C12) = Uanis(C13) = Uanis(C14) = Uanis(C15) = Uanis(C16) =
Uanis(C22) = Uanis(N2) = Uanis(C10) = Uanis(C9) = Uanis(C8) = Uanis(C7) =
Uanis(C6) = Uanis(C11) = Uanis(N4) = Uanis(C21) = Uanis(C20) = Uanis(C19) =
Uanis(C18) = Uanis(C17)
Uiso(C85) = Uiso(C59)
Uanis(F31) = Uanis(F23) = Uanis(F32) = Uanis(F7) = Uanis(F33) = Uanis(F21)
Uiso(F2) = Uiso(F36) = Uiso(F5) = Uiso(F35) = Uiso(F34) = Uiso(F14)
4. Others
 Fixed Sof: F14(0.5) N1(0.5) C5(0.5) C4(0.5) H4(0.5) C3(0.5) H3(0.5) C2(0.5)
 H2(0.5) C1(0.5) H1(0.5) F24(0.4) N2(0.5) C10(0.5) C9(0.5) H9(0.5) C8(0.5)
 H8(0.5) C7(0.5) H7(0.5) C6(0.5) F7(0.65) F2(0.5) F9(0.4) F19(0.4) F5(0.5)
 F21(0.65) F23(0.65) C59(0.65) C11(0.5) H11A(0.5) H11B(0.5) H11C(0.5) N3(0.5)
 C12(0.5) C13(0.5) H13(0.5) C14(0.5) H14(0.5) C15(0.5) H15(0.5) C16(0.5)
 N4(0.5) C21(0.5) H21(0.5) C20(0.5) H20(0.5) C19(0.5) H19(0.5) C18(0.5)
 H18(0.5) C17(0.5) C22(0.5) H22A(0.5) H22B(0.5) H22C(0.5) F3(0.4) F25(0.4)
 F13(0.4) F29(0.2) F30(0.2) F28(0.2) F31(0.35) F32(0.35) C85(0.35) F33(0.35)
 F35(0.5) F36(0.5) F34(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C02X(H02A,H02B), C031(H03A,H03B), C032(H03C,H03D), C033(H03E,H03F), C034(H03G,
 H03H), C035(H03I,H03J)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C2(H2), C1(H1), C62(H62), C40(H40), C37(H37), C66(H66),
 C24(H24), C64(H64), C9(H9), C8(H8), C7(H7), C78(H78), C012(H012), C70(H70),
 C82(H82), C30(H30), C74(H74), C80(H80), C39(H39), C01H(H01H), C38(H38),
 C01L(H01L), C28(H28), C01N(H01N), C48(H48), C72(H72), C42(H42), C54(H54),
 C31(H31), C46(H46), C25(H25), C32(H32), C27(H27), C58(H58), C26(H26), C34(H34),
  C49(H49), C52(H52), C56(H56), C33(H33), C45(H45), C44(H44), C51(H51),
 C50(H50), C43(H43), C13(H13), C14(H14), C15(H15), C21(H21), C20(H20), C19(H19),
  C18(H18)
5.c Fitted hexagon refined as free rotating group:
 N1(C5,C4,C3,C2,C1), N2(C10,C9,C8,C7,C6), N3(C12,C13,C14,C15,C16), N4(C21,C20,
 C19,C18,C17)
5.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              71470
_shelx_hkl_checksum              24548
_olex2_date_sample_data_collection 2021-03-12
_olex2_date_sample_submission    2021-03-06
_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 MEM067_150K
_olex2_submission_special_instructions 'No special instructions were received'