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_7708685
_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_absolute_configuration ad
_chemical_formula_moiety         'C51 H44 Cu N2 O P2, C32 H12 B F24'
_chemical_formula_sum            'C83 H56 B Cu F24 N2 O P2'
_chemical_formula_weight         1689.58
_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             2021-03-13
_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                79.4640(10)
_cell_angle_beta                 89.642(2)
_cell_angle_gamma                74.7590(10)
_cell_formula_units_Z            2
_cell_length_a                   10.7126(2)
_cell_length_b                   18.8554(4)
_cell_length_c                   19.4247(4)
_cell_measurement_reflns_used    79421
_cell_measurement_temperature    150
_cell_measurement_theta_max      57.01
_cell_measurement_theta_min      2.02
_cell_volume                     3718.16(13)
_computing_cell_refinement
;
X-Area Recipe 1.34.0.0 (STOE, 2019)
;
_computing_data_collection
;
X-Area Pilatus3_SV 1.31.154.0 (STOE, 2019)
;
_computing_data_reduction
;
X-Area Integrate 1.77.0.0 (STOE, 2019)
X-Area LANA 1.77.1.0 (STOE, 2019)
X-Area X-Red32 1.65.0.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.88, Darmstadt 2019
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150
_diffrn_detector                 Pilatus300K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS 300K'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_collimation    '1.2 0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34143
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            52347
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        53.597
_diffrn_reflns_theta_max         56.699
_diffrn_reflns_theta_min         2.015
_diffrn_source                   'Metaljet D2'
_diffrn_source_current           3.570
_diffrn_source_power             0.250
_diffrn_source_voltage           70
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.475
_exptl_absorpt_correction_T_max  0.2812
_exptl_absorpt_correction_T_min  0.0047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens in: F. R. Ahmed (Editor), "Crystallographic Computing", Munksgaard,
Copenhagen (1970), 255 - 270. Afterwards scaling of reflection intensities was
performed within STOE LANA. J. Koziskova, F. Hahn, J. Richter, J. Kozisek, Acta
Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Finally a spherical absorption correction was done within STOE LANA.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_description       block
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.972
_refine_diff_density_min         -1.233
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1037
_refine_ls_number_reflns         14623
_refine_ls_number_restraints     52
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0644
_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^)+(0.1117P)^2^+3.5908P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1716
_refine_ls_wR_factor_ref         0.1760
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13290
_reflns_number_total             14623
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt03239a2.cif
_cod_data_source_block           mem064_150k
_cod_database_code               7708685
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.693
_shelx_estimated_absorpt_t_min   0.588
_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
 F9-F11 \\sim F9-F23 \\sim F11-F23
 with sigma of 0.04
 C59-F9 \\sim C59-C54 \\sim C59-F11 \\sim C59-F23
 with sigma of 0.02
 C59-C54 \\sim C59-F3 \\sim C59-F25 \\sim C59-F13
 with sigma of 0.02
 F3-F25 \\sim F3-F13 \\sim F25-F13
 with sigma of 0.04
 C59-F7 \\sim C59-F29 \\sim C59-F27 \\sim C59-C54
 with sigma of 0.02
 F7-F29 \\sim F29-F27
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(F13) = Uanis(F11) = Uanis(F3) = Uanis(F23) = Uanis(F25) = Uanis(F9)
Uanis(F27) = Uanis(F11) = Uanis(F13) = Uanis(F29) = Uanis(F9) = Uanis(F25) =
Uanis(F7) = Uanis(F23) = Uanis(F3)
4. Others
 Fixed Sof: F9(0.5) F11(0.5) F23(0.5) F3(0.3) F25(0.3) F13(0.3) F27(0.2)
 F7(0.2) F29(0.2)
5.a Aromatic/amide H refined with riding coordinates:
 C77(H77), C81(H81), C69(H69), C53(H53), C20(H20), C57(H57), C24(H24),
 C73(H73), C61(H61), C37(H37), C79(H79), C38(H38), C33(H33), C39(H39), C32(H32),
  C14(H14), C55(H55), C65(H65), C18(H18), C34(H34), C63(H63), C41(H41),
 C23(H23), C45(H45), C71(H71), C22(H22), C47(H47), C49(H49), C21(H21), C51(H51),
  C48(H48), C2(H2), C17(H17), C42(H42), C4(H4), C9(H9), C15(H15), C16(H16),
 C50(H50), C7(H7), C8(H8), C43(H43), C44(H44), C3(H3)
5.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C36(H36A,H36B,H36C), C35(H35A,H35B,H35C), C11(H11A,H11B,
 H11C)
;
_shelx_res_checksum              37118
_shelx_hkl_checksum              44439
_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 MEM064_150K
_olex2_submission_special_instructions 'No special instructions were received'