The effects of introducing terminal alkenyl substituents into the 2,2'-bipyridine domain in [Cu(N^N)(P^P)]+ coordination compounds
Wöhler, Jannika; Meyer, Marco; Prescimone, Alessandro; Constable, Edwin C.; Housecroft, Catherine E.; Dalton Transactions  (2022) –; doi:10.1039/D2DT01799G

data_7710954
_publ_section_title
;
 The effects of introducing terminal alkenyl substituents into the
 2,2'-bipyridine domain in [Cu(N^N)(P^P)]+ coordination compounds
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT01799G
_journal_year                    2022
_chemical_formula_moiety         'C51 H44 Cu N2 O P2, F4.8 P, 1.2(F)'
_chemical_formula_sum            'C51 H44 Cu F6 N2 O P3'
_chemical_formula_weight         971.33
_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             2022-02-01
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-05-06 deposited with the CCDC.	2022-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.489(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0520(6)
_cell_length_b                   20.4008(11)
_cell_length_c                   15.9262(6)
_cell_measurement_reflns_used    56901
_cell_measurement_temperature    150
_cell_measurement_theta_max      73.49
_cell_measurement_theta_min      3.16
_cell_volume                     4557.1(4)
_computing_cell_refinement       'X-Area Recipe 1.37.0.0 (STOE, 2021)'
_computing_data_collection       'X-Area Pilatus3_SV 1.31.175.0 (STOE, 2021)'
_computing_data_reduction
;
X-Area Integrate 2.5.1.0 (STOE, 2021)
X-Area LANA 2.6.2.0 (STOE, 2021)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (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_detector                 'EIGER2 1M'
_diffrn_detector_area_resol_mean 13.33
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
 1961 frames, detector distance = 40 mm
;
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  Basel-Cu-Stoe
_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  270
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            39183
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         73.274
_diffrn_reflns_theta_min         3.525
_diffrn_source                   'Axo Cu'
_diffrn_source_current           1.00
_diffrn_source_power             0.050
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    2.226
_exptl_absorpt_correction_T_max  0.3653
_exptl_absorpt_correction_T_min  0.0886
_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    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2000
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of DCM and Et2O  by solvent layering'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.213
_exptl_crystal_size_min          0.17
_exptl_crystal_size_rad          0.210
_refine_diff_density_max         0.961
_refine_diff_density_min         -1.213
_refine_diff_density_rms         0.123
_refine_ls_extinction_coef       0.0023(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         8875
_refine_ls_number_restraints     195
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0844
_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^)+(0.1000P)^2^+16.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2064
_refine_ls_wR_factor_ref         0.2139
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8015
_reflns_number_total             8875
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt01799g2.cif
_cod_data_source_block           woj094_150k
_cod_database_code               7710954
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.703
_shelx_estimated_absorpt_t_min   0.606
_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
 P3-F12
 1.59 with sigma of 0.005
 P3-F7
 1.59 with sigma of 0.005
 P3-F4
 1.59 with sigma of 0.005
 P3-F2
 1.59 with sigma of 0.005
 P3-F8 = P3-F9
 1.59 with sigma of 0.005
 P3-F2 = P3-F11
 1.59 with sigma of 0.005
 F1-F4 \\sim F1-F6 \\sim F1-F2 \\sim F1-F5 \\sim F4-F6 \\sim F4-F3 \\sim F4-F2
\\sim F6-F3 \\sim F6-F5 \\sim F3-F2
 \\sim F3-F5 \\sim F2-F5
 with sigma of 0.04
 P3-F1 \\sim P3-F4 \\sim P3-F6 \\sim P3-F3 \\sim P3-F2 \\sim P3-F5
 with sigma of 0.02
 P3-F8 \\sim P3-F10 \\sim P3-F1 \\sim P3-F3 \\sim P3-F9 \\sim P3-F7
 with sigma of 0.02
 F8-F10 \\sim F8-F9 \\sim F10-F7 \\sim F9-F7
 with sigma of 0.04
 P3-F11 \\sim P3-F12 \\sim P3-F13 \\sim P3-F14
 with sigma of 0.02
 F14-F13 \\sim F14-F11
 with sigma of 0.04
 P3-F14 \\sim P3-F1 \\sim P3-F3 \\sim P3-F13 \\sim P3-F11
 with sigma of 0.02
3. Rigid bond restraints
 C15, C14, C13, C12
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C15 \\sim C14 \\sim C13 \\sim C12: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
Uanis(F4) = Uanis(F2) = Uanis(F5) = Uanis(F6)
Uanis(F7) = Uanis(F8) = Uanis(F9) = Uanis(F10)
Uanis(F14) = Uanis(F13) = Uanis(F12) = Uanis(F11)
5. Others
 Fixed Sof: F4(0.6) F6(0.6) F2(0.6) F5(0.6) F7(0.25) F10(0.25) F8(0.25)
 F9(0.25) F11(0.15) F14(0.15) F12(0.15) F13(0.15)
6.a Riding coordinates:
 C15(H15A,H15B)
6.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
6.c Aromatic/amide H refined with riding coordinates:
 C23(H23), C36(H36), C4(H4), C47(H47), C39(H39), C27(H27), C42(H42), C37(H37),
 C3(H3), C33(H33), C51(H51), C32(H32), C30(H30), C48(H48), C31(H31), C38(H38),
 C2(H2), C41(H41), C7(H7), C9(H9), C45(H45), C26(H26), C43(H43), C50(H50),
 C8(H8), C24(H24), C17(H17), C44(H44), C49(H49), C19(H19), C18(H18), C25(H25),
 C21(H21), C20(H20), C14(H14)
6.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              77294
_olex2_date_sample_data_collection 2022-01-28
_olex2_date_sample_submission    2022-01-21
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a mylar loop in perfluoroether oil'
_olex2_submission_original_sample_id WOJ094_150K
_olex2_submission_special_instructions 'No special instructions were received'
_stoe_detector_distance          '40.0 mm'
_stoe_detector_pixelsize_x       '0.075 mm'
_stoe_detector_pixelsize_y       '0.075 mm'
_stoe_detector_size_x            '8.0 cm'
_stoe_detector_size_y            '7.7 cm'
_stoe_evaluation_integration_a   7.2
_stoe_evaluation_integration_b   -0.1
_stoe_evaluation_integration_ems 0.014
_stoe_evaluation_lana_bis_l_even_max -
_stoe_evaluation_lana_bis_l_odd_max -
_stoe_evaluation_lana_bos_l_even_max 4
_stoe_evaluation_lana_bos_l_odd_max 1
_stoe_evaluation_lana_completeness 97.2
_stoe_evaluation_lana_dxs_max_order 1
_stoe_evaluation_lana_dys_max_order 1
_stoe_evaluation_lana_fs_max_order 3
_stoe_evaluation_lana_max_2theta_available 146.6
_stoe_evaluation_lana_max_2theta_desired 146.6
_stoe_evaluation_lana_mean_redundancy 4.4
_stoe_evaluation_lana_number_refls_after_or 39200
_stoe_evaluation_lana_number_refls_outliers 16400
_stoe_evaluation_lana_number_refls_total 55600
_stoe_evaluation_lana_number_refls_unique 8886
_stoe_evaluation_lana_number_refls_written 39200
_stoe_evaluation_lana_or_c1      0.035
_stoe_evaluation_lana_or_c2      0
_stoe_evaluation_lana_or_c3      0
_stoe_evaluation_lana_or_c4      0.7
_stoe_evaluation_lana_point_group 2/m
_stoe_evaluation_lana_table
;
2Theta          12.8   28.6   44.4   60.2   76.0   91.8  107.6  123.4  139.2
<Resolution>    5.39   2.93   2.00   1.50   1.25   1.08   0.95   0.88   0.83
N(total)          69   1000   2828   6707  12471  13331   8551   7134   3509
<Redundancy>     1.4    2.6    3.3    4.8    6.7    6.0    3.8    3.4    2.6
Complet. [%%]    66.7   98.5  100.0  100.0  100.0   99.9   99.8   99.6   82.4
<I/sigma>      263.1  144.5   83.2   43.1   29.1   21.1   15.0   11.7    7.9
R(int)         0.047  0.051  0.052  0.058  0.063  0.070  0.084  0.099  0.201
;
_stoe_measurement_identifier     WOJ094_150K
_stoe_measurement_max_exposure_per_frame '6.0 s'
_stoe_measurement_mean_exposure_per_frame '5.9 s'
_stoe_measurement_min_exposure_per_frame '2.0 s'
_stoe_measurement_total_exposure_time '3.2 h'
_stoe_measurement_total_frame_number 1961
_stoe_measurement_total_run_number 32
_stoe_measurement_tube_power     '50.0 W'