C‒H Activation of Fluoroarenes: Synthesis, Structure, and Luminescence Properties of Copper(I) and Gold(I) Complexes Bearing 2-Phenylpyridine Ligands
Molteni, Roberto; Edkins, Katharina; Haehnel, Martin; Steffen, Andreas; Organometallics 35 (2016) 629–; doi:10.1021/acs.organomet.5b00904

data_4088169
_publ_section_title
;
 C--H Activation of Fluoroarenes: Synthesis, Structure, and Luminescence
 Properties of Copper(I) and Gold(I) Complexes Bearing 2-Phenylpyridine
 Ligands
;
_journal_issue                   5
_journal_name_full               Organometallics
_journal_page_first              629
_journal_paper_doi               10.1021/acs.organomet.5b00904
_journal_volume                  35
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C38 H40 Cu F4 N3, 0.8(C4 H8 O)'
_chemical_formula_sum            'C41.2 H46.4 Cu F4 N3 O0.8'
_chemical_formula_weight         735.99
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_Int_Tables_number      4
_atom_sites_solution_primary     direct
_audit_creation_date             2013-09-02
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2013.08.21 svn.r2771 for OlexSys, GUI svn.r4586)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.772(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4322(4)
_cell_length_b                   16.8917(6)
_cell_length_c                   18.3072(7)
_cell_measurement_reflns_used    9474
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.76
_cell_measurement_theta_min      2.23
_cell_volume                     3817.7(2)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
'L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation (2013)'
_computing_structure_solution
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9995
_diffrn_measurement_device       'three-circle diffractometer'
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            92146
_diffrn_reflns_theta_full        25.9979
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.12
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_T_max  0.9124
_exptl_absorpt_correction_T_min  0.8504
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0521 before and 0.0494 after correction.
The Ratio of minimum to maximum transmission is 0.9320.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.2804
_exptl_crystal_description       block
_exptl_crystal_F_000             1546.0742
_exptl_crystal_preparation
'cut from a red prism and soaked in perfluoro polyether oil'
_exptl_crystal_recrystallization_method
'crystallised from THF and diethyl ether'
_exptl_crystal_size_max          0.358
_exptl_crystal_size_mid          0.301
_exptl_crystal_size_min          0.208
_refine_diff_density_max         1.3933
_refine_diff_density_min         -0.6208
_refine_diff_density_rms         0.0935
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.43(3)
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             18.1795
_refine_ls_goodness_of_fit_ref   1.0518
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    152
_refine_ls_number_parameters     884
_refine_ls_number_reflns         14992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0518
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0.0034
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0610P)^2^+6.3199P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1367
_reflns_Friedel_coverage         1.000
_reflns_limit_h_max              15
_reflns_limit_h_min              -15
_reflns_limit_k_max              20
_reflns_limit_k_min              -20
_reflns_limit_l_max              22
_reflns_limit_l_min              -22
_reflns_number_gt                12079
_reflns_number_total             14992
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            om5b00904_si_004.cif
_cod_data_source_block           13S108
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4088169
_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. Others
 Fixed Sof: C6S(0.6) H6Sa(0.6) H6Sb(0.6) O2S(0.6) C8S(0.6) H8Sa(0.6) H8Sb(0.6)
 C7S(0.6) H7Sa(0.6) H7Sb(0.6) C5S(0.6) H5Sa(0.6) H5Sb(0.6)
3.a Ternary CH refined with riding coordinates:
 C33A(H33A), C24A(H24A), C36A(H36A), C21A(H21A), C21B(H21B), C33B(H33B),
 C36B(H36B), C24B(H24B)
3.b Secondary CH2 refined with riding coordinates:
 C3S(H3Sa,H3Sb), C4S(H4Sa,H4Sb), C6S(H6Sa,H6Sb), C1S(H1Sa,H1Sb), C8S(H8Sa,
 H8Sb), C7S(H7Sa,H7Sb), C5S(H5Sa,H5Sb), C2S(H2Sa,H2Sb)
3.c Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C14A(H14A), C1A(H1A), C4A(H4A), C2A(H2A), C31A(H31A), C19A(H19A),
 C17A(H17A), C29A(H29A), C30A(H30A), C18A(H18A), C13A(H13A), C4B(H4B), C1B(H1B),
  C3B(H3B), C29B(H29B), C2B(H2B), C19B(H19B), C31B(H31B), C30B(H30B),
 C18B(H18B), C14B(H14B), C17B(H17B), C13B(H13B)
3.d Idealised Me refined as rotating group:
 C23A(H23a,H23b,H23c), C25A(H25a,H25b,H25c), C22A(H22a,H22b,H22c), C35A(H35a,
 H35b,H35c), C26A(H26a,H26b,H26c), C37A(H37a,H37b,H37c), C34A(H34a,H34b,H34c),
 C38A(H38a,H38b,H38c), C35B(H35d,H35e,H35f), C37B(H37d,H37e,H37f), C22B(H22d,
 H22e,H22f), C38B(H38d,H38e,H38f), C23B(H23d,H23e,H23f), C26B(H26d,H26e,H26f),
 C25B(H25d,H25e,H25f), C34B(H34d,H34e,H34f)
;