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_7708682
_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, F6 P, 0.5(C H2 Cl2), 0.3(C4 H10 O)'
_chemical_formula_sum            'C48.7 H41.7 Cl Cu F6 N2 O1.3 P3'
_chemical_formula_weight         981.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-05-03 deposited with the CCDC.	2021-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.379(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7279(9)
_cell_length_b                   16.4029(15)
_cell_length_c                   29.365(3)
_cell_measurement_reflns_used    9851
_cell_measurement_temperature    150
_cell_measurement_theta_max      70.264
_cell_measurement_theta_min      3.091
_cell_volume                     4656.6(8)
_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 0.975
_diffrn_measured_fraction_theta_max 0.951
_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           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            27579
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.291
_diffrn_reflns_theta_min         4.055
_diffrn_source_current           0.6
_diffrn_source_power             0.03
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.705
_exptl_absorpt_correction_T_max  0.7534
_exptl_absorpt_correction_T_min  0.6511
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0551 before and 0.0378 after correction.
The Ratio of minimum to maximum transmission is 0.8642.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       block
_exptl_crystal_F_000             2013
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of Et2O and DCM  by solvent layering'
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.697
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     615
_refine_ls_number_reflns         8442
_refine_ls_number_restraints     34
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0531
_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^)+(0.0571P)^2^+7.0759P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1414
_refine_ls_wR_factor_ref         0.1420
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8258
_reflns_number_total             8442
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt03239a2.cif
_cod_data_source_block           mem035_150k_0m
_cod_original_cell_volume        4656.6(7)
_cod_original_formula_sum        'C48.70 H41.70 Cl Cu F6 N2 O1.30 P3'
_cod_database_code               7708682
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.813
_shelx_estimated_absorpt_t_min   0.755
_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
 C52-C51 = C50-C49
 1.5 with sigma of 0.02
 C51-C52 \\sim C50-C49
 with sigma of 0.02
 O2-C49 \\sim O2-C51
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C50) \\sim Ueq, Uanis(C49) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C51)
\\sim Ueq, Uanis(C52) \\sim Ueq: with sigma of 0.005 and sigma for terminal
atoms of 0.01
Uanis(C52) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4. Others
 Fixed Sof: Cl1(0.5) Cl2(0.5) C48(0.5) H48A(0.5) H48B(0.5) O2(0.3) C49(0.3)
 H49A(0.3) H49B(0.3) C52(0.3) H52A(0.3) H52B(0.3) H52C(0.3) C50(0.3) H50A(0.3)
 H50B(0.3) H50C(0.3) C51(0.3) H51A(0.3) H51B(0.3)
5.a Riding coordinates:
 C50(H50A,H50B,H50C), C51(H51A,H51B)
5.b Secondary CH2 refined with riding coordinates:
 C48(H48A,H48B), C49(H49A,H49B)
5.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C32(H32), C35(H35), C43(H43), C19(H19), C37(H37), C23(H23),
 C14(H14), C26(H26), C29(H29), C11(H11), C47(H47), C17(H17), C21(H21), C15(H15),
  C33(H33), C44(H44), C45(H45), C8(H8), C20(H20), C3(H3), C27(H27), C22(H22),
 C34(H34), C9(H9), C28(H28), C46(H46), C10(H10), C16(H16), C38(H38), C41(H41),
 C5(H5), C4(H4), C39(H39), C40(H40)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C52(H52A,H52B,H52C)
;
_shelx_res_checksum              8021
_shelx_hkl_checksum              86777
_olex2_date_sample_data_collection 2020-02-26
_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 MEM035_150K
_olex2_submission_special_instructions 'No special instructions were received'