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_4088172
_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_formula_moiety         'C29 H40 Cu N3 O, 0.5(C2 H3 N)'
_chemical_formula_sum            'C30 H41.5 Cu N3.5 O'
_chemical_formula_weight         530.73
_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'
_audit_creation_date             2013-03-12
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.964(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.9466(13)
_cell_length_b                   15.9116(11)
_cell_length_c                   19.9904(13)
_cell_measurement_reflns_used    9704
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.45
_cell_volume                     5872.9(7)
_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
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_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 0.9999
_diffrn_measured_fraction_theta_max 0.9999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            89263
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.34
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.770
_exptl_absorpt_correction_T_max  0.7241
_exptl_absorpt_correction_T_min  0.6647
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0388 before and 0.0356 after correction.
The Ratio of minimum to maximum transmission is 0.9180.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2004
_exptl_crystal_description       block
_exptl_crystal_F_000             2267.3871
_exptl_crystal_preparation       'soaked in perfluoropolyether oil'
_exptl_crystal_recrystallization_method 'from acetonitrile'
_exptl_crystal_size_max          0.801
_exptl_crystal_size_mid          0.69
_exptl_crystal_size_min          0.585
_refine_diff_density_max         0.5352
_refine_diff_density_min         -0.5058
_refine_diff_density_rms         0.1619
_refine_ls_d_res_high            0.8106
_refine_ls_d_res_low             15.2128
_refine_ls_goodness_of_fit_ref   1.0521
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    137
_refine_ls_number_parameters     681
_refine_ls_number_reflns         11563
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0521
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0282
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0626P)^2^+2.6058P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0983
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -23
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              -14
_reflns_number_gt                10387
_reflns_number_total             11563
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            om5b00904_si_005.cif
_cod_data_source_block           13S023
_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               4088172
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H8b of C8b, H18b of C18b, H6a of C6a, H6b of C6b, H7a of C7a, H14a of C14a,
  H19a of C19a, {H11b,H11a} of C11a, H7b of C7b, H26a of C26a, H20b of C20b,
  H21a of C21a, H10b of C10b, H23a of C23a, H25d of C25b, H20a of C20a, H22b of
  C22b, H2a of C2a, H2b of C2b, H3aa of C3a, H19b of C19b, H3ba of C3b, H13g of
  C13b, H8a of C8a
 At 1.5 times of:
  {H13d,H13e,H13f} of C13a1, {H24a,H24b,H24c} of C24a, {H27a,H27b,H27c} of
  C27a, {H28a,H28b,H28c} of C28a, {H12a,H12b,H12c} of C12a2, {H12g,H12h,H12i}
  of C12b, {H13a,H13b,H13c} of C13a2, {H2sa,H2sb,H2sc} of C2s, {H12d,H12e,H12f}
  of C12a1, {H25a,H25b,H25c} of C25a, {H11c,H11d,H11e} of C11b, {H24d,H24e,
  H24f} of C24b, {H15d,H15e,H15f} of C15b, {H23b,H23c,H23d} of C23b, {H16a,H16b,
  H16c} of C16a, {H29a,H29b,H29c} of C29b, {H26b,H26c,H26d} of C26b, {H14b,H14c,
  H14d} of C14b, {H30a,H30b,H30c} of C30a, {H15a,H15b,H15c} of C15a, {H27d,H27e,
  H27f} of C27b
2. Others
 Sof(H11b)=1-Sof(H11a)=Sof(C13a2)=Sof(H13a)=Sof(H13b)=Sof(H13c)=Sof(C12a2)=
 Sof(H12a)=Sof(H12b)=Sof(H12c)=1-Sof(H11a)=1-Sof(H11a)=1-Sof(H11a)=1-Sof(H11a)=
 1-Sof(H11a)=1-Sof(H11a)=1-Sof(H11a)=1-Sof(H11a)
3.a Riding coordinates:
 N3b(H3b), N3a(H3a)
3.b Ternary CH refined with riding coordinates:
 C13b(H13g), C22b(H22b), C14a(H14a), C11a(H11b), C11a(H11a), C26a(H26a),
 C10b(H10b), C23a(H23a), C25b(H25d)
3.c Aromatic/amide H refined with riding coordinates:
 C3b(H3ba), C19b(H19b), C8a(H8a), C3a(H3aa), C2a(H2a), C2b(H2b), C8b(H8b),
 C18b(H18b), C6a(H6a), C6b(H6b), C7a(H7a), C19a(H19a), C7b(H7b), C20b(H20b),
 C21a(H21a), C20a(H20a)
3.d Idealised Me refined as rotating group:
 C23b(H23b,H23c,H23d), C16a(H16a,H16b,H16c), C29b(H29a,H29b,H29c), C26b(H26b,
 H26c,H26d), C14b(H14b,H14c,H14d), C30a(H30a,H30b,H30c), C15a(H15a,H15b,H15c),
 C27b(H27d,H27e,H27f), C15b(H15d,H15e,H15f), C28a(H28a,H28b,H28c), C25a(H25a,
 H25b,H25c), C24b(H24d,H24e,H24f), C27a(H27a,H27b,H27c), C2s(H2sa,H2sb,H2sc),
 C24a(H24a,H24b,H24c), C12b(H12g,H12h,H12i), C11b(H11c,H11d,H11e), C13a2(H13a,
 H13b,H13c), C12a2(H12a,H12b,H12c), C13a1(H13d,H13e,H13f), C12a1(H12d,H12e,H12f)
;