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_7708680
_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, 0.7(C3 H6 O), C24 H20 B'
_chemical_formula_sum            'C77.1 H68.2 B Cu N2 O1.7 P2'
_chemical_formula_weight         1186.22
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-12
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.7566(8)
_cell_length_b                   14.3706(4)
_cell_length_c                   30.3845(10)
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    150
_cell_measurement_theta_max      69.245
_cell_measurement_theta_min      3.074
_cell_volume                     12556.4(6)
_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 0.980
_diffrn_measured_fraction_theta_max 0.943
_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  0.0895
_diffrn_reflns_av_unetI/netI     0.0931
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            48359
_diffrn_reflns_point_group_measured_fraction_full 0.826
_diffrn_reflns_point_group_measured_fraction_max 0.793
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.005
_diffrn_reflns_theta_min         3.733
_diffrn_source_current           0.6
_diffrn_source_power             0.03
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.345
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5416
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1127 before and 0.0805 after correction.
The Ratio of minimum to maximum transmission is 0.7190.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       plate
_exptl_crystal_F_000             4979
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.776
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.10(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1507
_refine_ls_number_reflns         18870
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0592
_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^)+(0.0820P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1509
_reflns_Friedel_coverage         0.648
_reflns_Friedel_fraction_full    0.667
_reflns_Friedel_fraction_max     0.636
_reflns_number_gt                15392
_reflns_number_total             18870
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt03239a2.cif
_cod_data_source_block           mem054_150k
_cod_original_formula_sum        'C77.10 H68.20 B Cu N2 O1.70 P2'
_cod_database_code               7708680
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.889
_shelx_estimated_absorpt_t_min   0.747
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.90(3)
 0.10(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 O4-C154
 1.2 with sigma of 0.02
 C155-C154 = C156-C154
 1.48 with sigma of 0.005
 C155-C156
 2.58 with sigma of 0.02
 O4-C155 \\sim O4-C156
 with sigma of 0.02
 C155-C154 \\sim C156-C154
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C24) = Uanis(C23) = Uanis(C22) = Uanis(C21) = Uanis(C20) = Uanis(C19)
Uiso(O4) = Uiso(C154) = Uiso(C155) = Uiso(C156)
5. Others
 Fixed Sof: C154(0.4) C155(0.4) H15G(0.4) H15H(0.4) H15I(0.4) O4(0.4)
 C156(0.4) H15J(0.4) H15K(0.4) H15L(0.4)
6.a Riding coordinates:
 C155(H15G,H15H,H15I), C156(H15J,H15K,H15L)
6.b Aromatic/amide H refined with riding coordinates:
 C88(H88), C68(H68), C86(H86), C55(H55), C69(H69), C66(H66), C34(H34),
 C54(H54), C116(H116), C67(H67), C42(H42), C43(H43), C47(H47), C100(H100),
 C79(H79), C41(H41), C26(H26), C9(H9), C45(H45), C48(H48), C71(H71), C146(H146),
  C87(H87), C2(H2), C114(H114), C81(H81), C75(H75), C28(H28), C119(H119),
 C148(H148), C120(H120), C149(H149), C80(H80), C101(H101), C53(H53), C74(H74),
 C117(H117), C4(H4), C118(H118), C113(H113), C129(H129), C60(H60), C98(H98),
 C110(H110), C32(H32), C58(H58), C59(H59), C122(H122), C92(H92), C33(H33),
 C27(H27), C112(H112), C111(H111), C130(H130), C8(H8), C44(H44), C3(H3),
 C102(H102), C99(H99), C147(H147), C140(H140), C126(H126), C128(H128),
 C137(H137), C14(H14), C7(H7), C49(H49), C93(H93), C65(H65), C51(H51),
 C104(H104), C73(H73), C106(H106), C18(H18), C134(H134), C150(H150), C136(H136),
  C138(H138), C144(H144), C72(H72), C105(H105), C50(H50), C132(H132), C96(H96),
 C108(H108), C141(H141), C107(H107), C135(H135), C131(H131), C20(H20), C94(H94),
  C123(H123), C95(H95), C125(H125), C142(H142), C124(H124), C143(H143),
 C17(H17), C24(H24), C15(H15), C16(H16), C21(H21), C22(H22), C23(H23)
6.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C38(H38A,H38B,H38C), C62(H62A,H62B,H62C), C89(H89A,H89B,
 H89C), C63(H63A,H63B,H63C), C90(H90A,H90B,H90C), C37(H37A,H37B,H37C), C12(H12A,
 H12B,H12C), C152(H15A,H15B,H15C), C153(H15D,H15E,H15F)
;
_shelx_res_checksum              22391
_shelx_hkl_checksum              45681
_olex2_date_sample_data_collection 2021-03-10
_olex2_date_sample_submission    2021-03-05
_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 MEM054_150K
_olex2_submission_special_instructions 'No special instructions were received'