#------------------------------------------------------------------------------
#$Date: 2017-09-07 03:14:02 +0300 (Thu, 07 Sep 2017) $
#$Revision: 200244 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/63/4126365.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4126365
loop_
_publ_author_name
'Kundu, Subrata'
'Greene, Christine'
'Williams, Kamille D.'
'Salvador, Tolani K.'
'Bertke, Jeffery A.'
'Cundari, Thomas R.'
'Warren, Timothy H.'
_publ_contact_author             'Timothy H. Warren'
_publ_section_title
;
 Three-Coordinate Copper(II) Aryls: Key Intermediates in C-O Bond
 Formation.
;
_journal_issue                   27
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9112
_journal_page_last               9115
_journal_paper_doi               10.1021/jacs.7b04046
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C27 H19 Cu F11 N2'
_chemical_formula_sum            'C27 H19 Cu F11 N2'
_chemical_formula_weight         643.98
_chemical_name_systematic        '[Me2NNF6]Cu-C6F5'
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 102.5220(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6083(2)
_cell_length_b                   24.5638(6)
_cell_length_c                   14.4862(4)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3825
_cell_measurement_theta_min      2.865
_cell_volume                     2642.91(12)
_computing_cell_refinement       'Bruker APEXII'
_computing_data_collection       'Bruker APEXII'
_computing_data_reduction        'Bruker APEXII'
_computing_molecular_graphics
'XSEED; Barbour, L. J. (2001) J. Supramol. Chem. 1, 189-191.'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            31630
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        28.000
_diffrn_reflns_theta_max         28.419
_diffrn_reflns_theta_min         1.658
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.924
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6386
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS based on Blessing's method; Blessing, Acta Cryst. (1995) A51 33-38'
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1292
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         6634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0281
_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/[σ²(Fo²)+(0.0400P)²+0.9996P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0744
_refine_ls_wR_factor_ref         0.0778
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5515
_reflns_number_total             6634
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b04046_si_005.cif
_cod_data_source_block           3Me
_cod_database_code               4126365
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.806
_shelx_estimated_absorpt_t_max   0.894
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Cu1 Cu 0.46991(2) 0.14759(2) 0.29910(2) 0.01649(6) Uani 1 1 d . .
F1 F 0.87916(14) 0.02485(4) 0.55417(7) 0.0343(2) Uani 1 1 d . .
F2 F 0.86574(14) 0.10870(4) 0.58968(7) 0.0348(2) Uani 1 1 d . .
F3 F 0.64499(14) 0.05569(5) 0.59669(8) 0.0402(3) Uani 1 1 d . .
F4 F 0.75925(17) -0.04181(4) 0.26740(8) 0.0427(3) Uani 1 1 d . .
F5 F 0.48129(15) -0.03513(4) 0.19504(10) 0.0444(3) Uani 1 1 d . .
F6 F 0.68587(15) 0.00725(4) 0.14360(7) 0.0333(2) Uani 1 1 d . .
F7 F 0.12045(13) 0.20423(4) 0.34277(7) 0.0291(2) Uani 1 1 d . .
F8 F 0.03960(14) 0.31104(4) 0.34629(8) 0.0374(3) Uani 1 1 d . .
F9 F 0.26977(15) 0.38689(4) 0.30361(8) 0.0388(3) Uani 1 1 d . .
F10 F 0.58238(14) 0.35533(4) 0.25693(8) 0.0312(2) Uani 1 1 d . .
F11 F 0.66031(13) 0.24874(4) 0.24920(7) 0.0271(2) Uani 1 1 d . .
N1 N 0.58706(16) 0.12612(5) 0.42517(9) 0.0171(2) Uani 1 1 d . .
N2 N 0.50677(17) 0.08196(5) 0.24193(9) 0.0182(2) Uani 1 1 d . .
C1 C 0.67936(19) 0.08070(6) 0.44358(11) 0.0186(3) Uani 1 1 d . .
C2 C 0.6999(2) 0.04109(6) 0.37692(11) 0.0208(3) Uani 1 1 d . .
H2 H 0.7804 0.0118 0.3977 0.025 Uiso 1 1 calc R U
C3 C 0.6106(2) 0.04181(6) 0.28255(11) 0.0194(3) Uani 1 1 d . .
C4 C 0.7678(2) 0.06760(7) 0.54641(12) 0.0242(3) Uani 1 1 d . .
C5 C 0.6339(2) -0.00760(6) 0.22228(13) 0.0254(3) Uani 1 1 d . .
C6 C 0.55273(19) 0.16409(6) 0.49502(10) 0.0171(3) Uani 1 1 d . .
C7 C 0.3974(2) 0.15654(6) 0.53112(11) 0.0205(3) Uani 1 1 d . .
C8 C 0.3547(2) 0.19644(7) 0.59080(11) 0.0262(3) Uani 1 1 d . .
H8 H 0.2529 0.1917 0.6180 0.031 Uiso 1 1 calc R U
C9 C 0.4582(2) 0.24288(7) 0.61108(12) 0.0291(4) Uani 1 1 d . .
H9 H 0.4257 0.2701 0.6509 0.035 Uiso 1 1 calc R U
C10 C 0.6095(2) 0.24995(7) 0.57343(12) 0.0259(3) Uani 1 1 d . .
H10 H 0.6793 0.2822 0.5875 0.031 Uiso 1 1 calc R U
C11 C 0.6608(2) 0.21063(6) 0.51542(11) 0.0209(3) Uani 1 1 d . .
C12 C 0.38982(19) 0.08175(6) 0.14996(11) 0.0185(3) Uani 1 1 d . .
C13 C 0.4461(2) 0.10718(6) 0.07443(11) 0.0224(3) Uani 1 1 d . .
C14 C 0.3251(2) 0.10858(7) -0.01303(12) 0.0277(3) Uani 1 1 d . .
H14 H 0.3606 0.1247 -0.0657 0.033 Uiso 1 1 calc R U
C15 C 0.1541(2) 0.08677(7) -0.02400(12) 0.0297(4) Uani 1 1 d . .
H15 H 0.0738 0.0877 -0.0842 0.036 Uiso 1 1 calc R U
C16 C 0.0995(2) 0.06366(7) 0.05217(12) 0.0276(3) Uani 1 1 d . .
H16 H -0.0189 0.0493 0.0438 0.033 Uiso 1 1 calc R U
C17 C 0.2145(2) 0.06104(6) 0.14076(12) 0.0233(3) Uani 1 1 d . .
C18 C 0.2745(2) 0.10840(7) 0.50363(12) 0.0270(3) Uani 1 1 d . .
H18A H 0.1975 0.1041 0.5493 0.040 Uiso 1 1 calc R U
H18B H 0.3468 0.0754 0.5032 0.040 Uiso 1 1 calc R U
H18C H 0.1992 0.1144 0.4404 0.040 Uiso 1 1 calc R U
C19 C 0.8263(2) 0.21869(7) 0.47579(12) 0.0272(3) Uani 1 1 d . .
H19A H 0.8585 0.2574 0.4786 0.041 Uiso 1 1 calc R U
H19B H 0.8019 0.2064 0.4099 0.041 Uiso 1 1 calc R U
H19C H 0.9262 0.1976 0.5131 0.041 Uiso 1 1 calc R U
C20 C 0.6300(2) 0.13265(8) 0.08678(13) 0.0314(4) Uani 1 1 d . .
H20A H 0.6514 0.1430 0.0248 0.047 Uiso 1 1 calc R U
H20B H 0.7217 0.1064 0.1168 0.047 Uiso 1 1 calc R U
H20C H 0.6363 0.1651 0.1267 0.047 Uiso 1 1 calc R U
C21 C 0.1513(2) 0.03721(8) 0.22388(13) 0.0313(4) Uani 1 1 d . .
H21A H 0.2336 0.0081 0.2524 0.047 Uiso 1 1 calc R U
H21B H 0.0299 0.0223 0.2024 0.047 Uiso 1 1 calc R U
H21C H 0.1492 0.0657 0.2709 0.047 Uiso 1 1 calc R U
C22 C 0.3949(2) 0.22266(6) 0.29750(10) 0.0184(3) Uani 1 1 d . .
C23 C 0.2395(2) 0.24090(6) 0.32183(11) 0.0211(3) Uani 1 1 d . .
C24 C 0.1947(2) 0.29530(7) 0.32374(12) 0.0252(3) Uani 1 1 d . .
C25 C 0.3099(2) 0.33369(6) 0.30165(12) 0.0259(3) Uani 1 1 d . .
C26 C 0.4678(2) 0.31776(6) 0.27738(11) 0.0230(3) Uani 1 1 d . .
C27 C 0.5048(2) 0.26287(6) 0.27501(11) 0.0199(3) Uani 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 Cu1 N1 95.82(5)
N2 Cu1 C22 153.56(6)
N1 Cu1 C22 110.39(6)
C1 N1 C6 125.25(13)
C1 N1 Cu1 122.85(10)
C6 N1 Cu1 111.83(9)
C3 N2 C12 127.08(13)
C3 N2 Cu1 125.61(11)
C12 N2 Cu1 107.09(9)
N1 C1 C2 125.68(14)
N1 C1 C4 118.61(13)
C2 C1 C4 115.67(13)
C3 C2 C1 124.38(14)
N2 C3 C2 124.51(14)
N2 C3 C5 118.12(14)
C2 C3 C5 117.36(13)
F2 C4 F3 107.23(14)
F2 C4 F1 106.04(12)
F3 C4 F1 106.70(13)
F2 C4 C1 112.51(13)
F3 C4 C1 111.41(13)
F1 C4 C1 112.55(13)
F5 C5 F4 108.15(14)
F5 C5 F6 106.68(14)
F4 C5 F6 106.17(13)
F5 C5 C3 111.83(13)
F4 C5 C3 112.36(14)
F6 C5 C3 111.31(13)
C11 C6 C7 122.11(14)
C11 C6 N1 119.26(13)
C7 C6 N1 118.11(13)
C8 C7 C6 117.84(15)
C8 C7 C18 120.15(14)
C6 C7 C18 121.96(14)
C9 C8 C7 121.01(15)
C8 C9 C10 120.21(15)
C9 C10 C11 121.05(16)
C10 C11 C6 117.75(14)
C10 C11 C19 120.42(14)
C6 C11 C19 121.83(14)
C13 C12 C17 121.99(14)
C13 C12 N2 119.34(13)
C17 C12 N2 118.32(13)
C14 C13 C12 117.75(15)
C14 C13 C20 120.66(15)
C12 C13 C20 121.59(14)
C15 C14 C13 120.88(16)
C16 C15 C14 120.32(16)
C15 C16 C17 121.22(16)
C16 C17 C12 117.73(15)
C16 C17 C21 120.61(15)
C12 C17 C21 121.66(14)
C27 C22 C23 115.16(13)
C27 C22 Cu1 119.64(11)
C23 C22 Cu1 125.12(11)
F7 C23 C22 119.45(13)
F7 C23 C24 117.24(14)
C22 C23 C24 123.29(15)
F8 C24 C25 119.80(14)
F8 C24 C23 121.05(15)
C25 C24 C23 119.14(14)
F9 C25 C24 120.24(15)
F9 C25 C26 119.72(16)
C24 C25 C26 120.04(14)
F10 C26 C25 120.20(14)
F10 C26 C27 121.28(14)
C25 C26 C27 118.52(15)
F11 C27 C22 119.37(13)
F11 C27 C26 116.79(14)
C22 C27 C26 123.84(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cu1 N2 1.8612(12)
Cu1 N1 1.9241(12)
Cu1 C22 1.9290(14)
F1 C4 1.3387(18)
F2 C4 1.329(2)
F3 C4 1.3356(19)
F4 C5 1.3313(19)
F5 C5 1.3278(19)
F6 C5 1.335(2)
F7 C23 1.3579(18)
F8 C24 1.3473(18)
F9 C25 1.3438(18)
F10 C26 1.3458(18)
F11 C27 1.3606(17)
N1 C1 1.3145(19)
N1 C6 1.4411(19)
N2 C3 1.3195(19)
N2 C12 1.4327(19)
C1 C2 1.403(2)
C1 C4 1.530(2)
C2 C3 1.389(2)
C3 C5 1.528(2)
C6 C11 1.402(2)
C6 C7 1.405(2)
C7 C8 1.391(2)
C7 C18 1.507(2)
C8 C9 1.381(3)
C9 C10 1.388(2)
C10 C11 1.390(2)
C11 C19 1.506(2)
C12 C13 1.405(2)
C12 C17 1.407(2)
C13 C14 1.396(2)
C13 C20 1.508(2)
C14 C15 1.384(3)
C15 C16 1.382(3)
C16 C17 1.389(2)
C17 C21 1.509(2)
C22 C27 1.378(2)
C22 C23 1.379(2)
C23 C24 1.381(2)
C24 C25 1.372(2)
C25 C26 1.379(2)
C26 C27 1.379(2)
