#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:45:44 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179862 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/58/7015871.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_7015871
loop_
_publ_author_name
'Eckenhoff, William T.'
'Pintauer, Tomislav'
_publ_section_title
;
 Atom transfer radical addition (ATRA) catalyzed by copper complexes
 with tris[2-(dimethylamino)ethyl]amine (Me6TREN) ligand in the
 presence of free-radical diazo initiator AIBN.
;
_journal_issue                   18
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4909
_journal_page_last               4917
_journal_paper_doi               10.1039/c1dt10189g
_journal_volume                  40
_journal_year                    2011
_chemical_formula_moiety         'C12 H30 Br Cu N4, Br'
_chemical_formula_sum            'C12 H30 Br2 Cu N4'
_chemical_formula_weight         453.76
_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                   12.0512(3)
_cell_length_b                   12.0512(3)
_cell_length_c                   12.0512(3)
_cell_measurement_reflns_used    8713
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.502
_cell_measurement_theta_min      2.39
_cell_volume                     1750.21(8)
_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 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23236
_diffrn_reflns_theta_full        32.94
_diffrn_reflns_theta_max         32.94
_diffrn_reflns_theta_min         2.39
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         2153
_exptl_absorpt_coefficient_mu    5.808
_exptl_absorpt_correction_T_max  0.473
_exptl_absorpt_correction_T_min  0.244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.722
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rhomboids
_exptl_crystal_F_000             916
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.129
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.006(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     60
_refine_ls_number_reflns         2153
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0227
_refine_ls_R_factor_gt           0.0185
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0231P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0433
_refine_ls_wR_factor_ref         0.0443
_reflns_number_gt                1994
_reflns_number_total             2153
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1dt10189g.txt
_cod_data_source_block           '[Cu(Me6TREN)Br][Br]'
_cod_database_code               7015871
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.117707(12) 0.117707(12) 0.117707(12) 0.02311(6) Uani 1 3 d S . .
Cu1 Cu 0.232761(15) 0.232761(15) 0.232761(15) 0.01639(6) Uani 1 3 d S . .
C1 C 0.43121(13) 0.36419(13) 0.26614(14) 0.0227(3) Uani 1 1 d . . .
H1A H 0.4881 0.3077 0.2735 0.027 Uiso 1 1 calc R . .
H1B H 0.4605 0.4332 0.2954 0.027 Uiso 1 1 calc R . .
N2 N 0.34725(11) 0.27628(11) 0.10274(11) 0.0214(3) Uani 1 1 d . . .
C2 C 0.40151(14) 0.37884(14) 0.14480(13) 0.0237(3) Uani 1 1 d . . .
H2A H 0.3516 0.4414 0.1364 0.028 Uiso 1 1 calc R . .
H2B H 0.4681 0.3938 0.1021 0.028 Uiso 1 1 calc R . .
N1 N 0.33078(10) 0.33078(10) 0.33078(10) 0.0186(4) Uani 1 3 d S . .
C3 C 0.29758(16) 0.29887(14) -0.00706(14) 0.0289(3) Uani 1 1 d . . .
H3A H 0.2441 0.3576 -0.0004 0.043 Uiso 1 1 calc R . .
H3B H 0.2616 0.2331 -0.0340 0.043 Uiso 1 1 calc R . .
H3C H 0.3547 0.3206 -0.0581 0.043 Uiso 1 1 calc R . .
C4 C 0.43152(15) 0.18723(15) 0.08787(15) 0.0287(4) Uani 1 1 d . . .
H4A H 0.3956 0.1206 0.0631 0.043 Uiso 1 1 calc R . .
H4B H 0.4681 0.1735 0.1573 0.043 Uiso 1 1 calc R . .
H4C H 0.4851 0.2102 0.0336 0.043 Uiso 1 1 calc R . .
Br2 Br 0.683701(15) 0.183701(15) 0.316299(15) 0.02710(7) Uani 1 3 d S . .
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
Br1 0.02311(6) 0.02311(6) 0.02311(6) -0.00332(5) -0.00332(5) -0.00332(5)
Cu1 0.01639(6) 0.01639(6) 0.01639(6) -0.00039(6) -0.00039(6) -0.00039(6)
C1 0.0198(6) 0.0226(7) 0.0255(7) -0.0021(6) 0.0014(6) -0.0051(5)
N2 0.0244(6) 0.0190(6) 0.0207(6) 0.0001(5) 0.0039(5) -0.0036(5)
C2 0.0264(8) 0.0196(7) 0.0251(7) -0.0005(6) 0.0054(6) -0.0045(6)
N1 0.0186(4) 0.0186(4) 0.0186(4) -0.0011(4) -0.0011(4) -0.0011(4)
C3 0.0368(9) 0.0301(8) 0.0197(7) 0.0032(6) 0.0022(6) -0.0048(7)
C4 0.0306(8) 0.0244(7) 0.0309(8) -0.0047(7) 0.0089(7) -0.0002(7)
Br2 0.02710(7) 0.02710(7) 0.02710(7) -0.00204(7) -0.00204(7) 0.00204(7)
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
_geom_angle_publ_flag
N1 Cu1 N2 84.81(4) . 9 ?
N1 Cu1 N2 84.81(4) . 5 ?
N2 Cu1 N2 119.192(11) 9 5 ?
N1 Cu1 N2 84.81(4) . . ?
N2 Cu1 N2 119.191(11) 9 . ?
N2 Cu1 N2 119.191(11) 5 . ?
N1 Cu1 Br1 180.00(4) . . ?
N2 Cu1 Br1 95.19(4) 9 . ?
N2 Cu1 Br1 95.19(4) 5 . ?
N2 Cu1 Br1 95.19(4) . . ?
N1 C1 C2 110.06(13) . . ?
N1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.2 . . ?
C3 N2 C2 109.28(13) . . ?
C3 N2 C4 107.55(13) . . ?
C2 N2 C4 109.89(13) . . ?
C3 N2 Cu1 115.92(10) . . ?
C2 N2 Cu1 103.66(9) . . ?
C4 N2 Cu1 110.45(10) . . ?
N2 C2 C1 109.62(13) . . ?
N2 C2 H2A 109.7 . . ?
C1 C2 H2A 109.7 . . ?
N2 C2 H2B 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C1 N1 C1 110.14(9) . 9 ?
C1 N1 C1 110.14(9) . 5 ?
C1 N1 C1 110.14(9) 9 5 ?
C1 N1 Cu1 108.79(10) . . ?
C1 N1 Cu1 108.79(10) 9 . ?
C1 N1 Cu1 108.79(10) 5 . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Cu1 2.4016(4) . ?
Cu1 N1 2.046(2) . ?
Cu1 N2 2.1527(13) 9 ?
Cu1 N2 2.1527(13) 5 ?
Cu1 N2 2.1527(13) . ?
C1 N1 1.4946(16) . ?
C1 C2 1.516(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
N2 C3 1.478(2) . ?
N2 C2 1.487(2) . ?
N2 C4 1.488(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
N1 C1 1.4946(16) 9 ?
N1 C1 1.4946(16) 5 ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
