#------------------------------------------------------------------------------
#$Date: 2016-03-23 22:52:40 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179494 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/91/4339107.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_4339107
loop_
_publ_author_name
'Eckenhoff, William T.'
'Pintauer, Tomislav'
_publ_section_title
;
 Atom transfer radical addition in the presence of catalytic amounts of
 copper(I/II) complexes with tris(2-pyridylmethyl)amine.
;
_journal_issue                   15
_journal_name_full               'Inorganic chemistry'
_journal_page_first              5844
_journal_page_last               5846
_journal_paper_doi               10.1021/ic700908m
_journal_volume                  46
_journal_year                    2007
_chemical_formula_moiety         'C18 H18 Cl Cu N4, Cl'
_chemical_formula_sum            'C18 H18 Cl2 Cu N4'
_chemical_formula_weight         424.81
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           198
_symmetry_cell_setting           cubic
_symmetry_space_group_name_Hall  'P 2ac 2ab 3'
_symmetry_space_group_name_H-M   'P 21 3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.41570(10)
_cell_length_b                   12.41570(10)
_cell_length_c                   12.41570(10)
_cell_measurement_reflns_used    9852
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.53
_cell_measurement_theta_min      2.32
_cell_volume                     1913.88(3)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Smart ApexII'
_diffrn_measurement_method       'φ and ω Scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            35485
_diffrn_reflns_theta_full        32.79
_diffrn_reflns_theta_max         32.79
_diffrn_reflns_theta_min         2.32
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         2342
_exptl_absorpt_coefficient_mu    1.428
_exptl_absorpt_correction_T_max  0.767
_exptl_absorpt_correction_T_min  0.545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rhomboids
_exptl_crystal_F_000             868
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.186
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.011(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         2342
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0184
_refine_ls_R_factor_gt           0.0170
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0260P)²+0.1634P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0455
_refine_ls_wR_factor_ref         0.0460
_reflns_number_gt                2253
_reflns_number_total             2342
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic700908m-file006.cif
_cod_data_source_block           CuTPMACl2
_cod_database_code               4339107
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'z, x, y'
'z+1/2, -x+1/2, -y'
'-z+1/2, -x, y+1/2'
'-z, x+1/2, -y+1/2'
'y, z, x'
'-y, z+1/2, -x+1/2'
'y+1/2, -z+1/2, -x'
'-y+1/2, -z, x+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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.83570(8) 0.47557(8) 0.02500(8) 0.02029(18) Uani 1 1 d .
H1A H 0.8093 0.4340 -0.0357 0.024 Uiso 1 1 calc R
H1B H 0.8752 0.5370 -0.0027 0.024 Uiso 1 1 calc R
Cu1 Cu 0.812686(9) 0.312686(9) 0.187314(9) 0.01698(5) Uani 1 3 d S
Cl2 Cl 0.080044(18) 0.580044(18) 0.919956(18) 0.01813(7) Uani 1 3 d S
Cl1 Cl 0.708668(18) 0.208668(18) 0.291333(18) 0.02607(9) Uani 1 3 d S
N1 N 0.90793(6) 0.40793(6) 0.09207(6) 0.0170(2) Uani 1 3 d S
N2 N 0.71054(6) 0.44387(6) 0.16961(6) 0.01757(15) Uani 1 1 d .
C3 C 0.69161(9) 0.61170(8) 0.07628(8) 0.02322(18) Uani 1 1 d .
H3 H 0.7158 0.6589 0.0234 0.028 Uiso 1 1 calc R
C5 C 0.56958(9) 0.56573(8) 0.21832(9) 0.02335(19) Uani 1 1 d .
H5 H 0.5104 0.5815 0.2615 0.028 Uiso 1 1 calc R
C2 C 0.74257(8) 0.51361(8) 0.09235(8) 0.01823(17) Uani 1 1 d .
C6 C 0.62499(8) 0.46917(8) 0.23082(8) 0.01959(18) Uani 1 1 d .
H6 H 0.6021 0.4207 0.2831 0.024 Uiso 1 1 calc R
C4 C 0.60384(9) 0.63842(9) 0.14032(9) 0.0254(2) Uani 1 1 d .
H4 H 0.5686 0.7039 0.1312 0.031 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0208(4) 0.0221(4) 0.0179(4) 0.0062(3) 0.0021(3) -0.0001(3)
Cu1 0.01698(5) 0.01698(5) 0.01698(5) 0.00310(4) 0.00310(4) -0.00310(4)
Cl2 0.01813(7) 0.01813(7) 0.01813(7) 0.00125(7) 0.00125(7) -0.00125(7)
Cl1 0.02607(9) 0.02607(9) 0.02607(9) 0.00719(8) 0.00719(8) -0.00719(8)
N1 0.0170(2) 0.0170(2) 0.0170(2) 0.0018(3) 0.0018(3) -0.0018(3)
N2 0.0179(3) 0.0174(3) 0.0175(3) 0.0020(3) 0.0019(3) -0.0009(3)
C3 0.0249(4) 0.0200(4) 0.0248(4) 0.0057(3) -0.0009(4) 0.0001(4)
C5 0.0224(4) 0.0224(4) 0.0253(4) -0.0024(4) 0.0027(4) 0.0025(3)
C2 0.0182(4) 0.0187(4) 0.0179(4) 0.0032(3) -0.0001(3) -0.0012(3)
C6 0.0200(4) 0.0196(4) 0.0192(4) -0.0001(3) 0.0029(3) -0.0008(3)
C4 0.0259(5) 0.0199(4) 0.0306(5) 0.0013(4) -0.0027(4) 0.0041(4)
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 C1 C2 109.29(8) . .
N1 C1 H1A 109.8 . .
C2 C1 H1A 109.8 . .
N1 C1 H1B 109.8 . .
C2 C1 H1B 109.8 . .
H1A C1 H1B 108.3 . .
N1 Cu1 N2 80.71(2) . 11_556
N1 Cu1 N2 80.71(2) . 8_645
N2 Cu1 N2 117.448(12) 11_556 8_645
N1 Cu1 N2 80.71(2) . .
N2 Cu1 N2 117.447(12) 11_556 .
N2 Cu1 N2 117.447(12) 8_645 .
N1 Cu1 Cl1 180.000(19) . .
N2 Cu1 Cl1 99.29(2) 11_556 .
N2 Cu1 Cl1 99.29(2) 8_645 .
N2 Cu1 Cl1 99.29(2) . .
C1 N1 C1 111.31(6) . 11_556
C1 N1 C1 111.30(6) . 8_645
C1 N1 C1 111.31(6) 11_556 8_645
C1 N1 Cu1 107.57(6) . .
C1 N1 Cu1 107.57(6) 11_556 .
C1 N1 Cu1 107.57(6) 8_645 .
C6 N2 C2 118.96(8) . .
C6 N2 Cu1 127.34(6) . .
C2 N2 Cu1 113.45(6) . .
C2 C3 C4 119.02(9) . .
C2 C3 H3 120.5 . .
C4 C3 H3 120.5 . .
C4 C5 C6 119.07(10) . .
C4 C5 H5 120.5 . .
C6 C5 H5 120.5 . .
N2 C2 C3 122.03(9) . .
N2 C2 C1 114.82(8) . .
C3 C2 C1 123.14(9) . .
N2 C6 C5 121.97(9) . .
N2 C6 H6 119.0 . .
C5 C6 H6 119.0 . .
C3 C4 C5 118.93(9) . .
C3 C4 H4 120.5 . .
C5 C4 H4 120.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.4842(11) .
C1 C2 1.5031(14) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
Cu1 N1 2.0481(14) .
Cu1 N2 2.0759(8) 11_556
Cu1 N2 2.0759(8) 8_645
Cu1 N2 2.0759(8) .
Cu1 Cl1 2.2369(4) .
N1 C1 1.4842(11) 11_556
N1 C1 1.4843(11) 8_645
N2 C6 1.3432(12) .
N2 C2 1.3520(12) .
C3 C2 1.3869(14) .
C3 C4 1.3893(16) .
C3 H3 0.9300 .
C5 C4 1.3903(15) .
C5 C6 1.3910(14) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C4 H4 0.9300 .
