#------------------------------------------------------------------------------
#$Date: 2016-03-24 17:09:42 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179679 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/01/7000139.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_7000139
loop_
_publ_author_name
'Boldron, Christophe'
'Ozalp-Yaman, Seniz'
'Gamez, Patrick'
'Tooke, Duncan M.'
'Spek, Anthony L.'
'Reedijk, Jan'
_publ_section_title
;
 Selective copper(II)-mediated oxidative coupling of a nucleophilic
 reagent to the para-methyl group of 2,4,6-trimethylphenol.
;
_journal_issue                   21
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3535
_journal_page_last               3541
_journal_paper_doi               10.1039/b507199b
_journal_year                    2005
_chemical_formula_moiety         'C21 H19 Cl3 Cu2 N4 O'
_chemical_formula_sum            'C21 H19 Cl3 Cu2 N4 O'
_chemical_formula_weight         576.83
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 114.620(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.4463(10)
_cell_length_b                   7.7606(10)
_cell_length_c                   18.5145(9)
_cell_measurement_reflns_used    27
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      18.872
_cell_measurement_theta_min      6.271
_cell_volume                     2148.2(3)
_computing_cell_refinement       'DIRAX (Duisenberg, 1992)'
_computing_data_collection       'Nonius Collect (Hooft, 1998)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'Omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            28223
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    2.376
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            'dark green-blue'
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         2462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0417P)²+3.4028P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0818
_reflns_number_gt                1965
_reflns_number_total             2462
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b507199b.txt
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7000139
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.06968(2) 0.33250(4) 0.344141(18) 0.02199(11) Uani 1 1 d . . .
Cl2 Cl -0.01076(4) 0.22851(10) 0.41030(4) 0.03000(18) Uani 1 1 d . . .
Cl3 Cl 0.0000 0.58417(12) 0.2500 0.0265(2) Uani 1 2 d S . .
O4 O 0.0000 0.2061(3) 0.2500 0.0231(6) Uani 1 2 d S . .
N6 N 0.18783(14) 0.2968(3) 0.33347(13) 0.0212(5) Uani 1 1 d . . .
N17 N 0.15388(14) 0.4608(3) 0.44031(13) 0.0234(5) Uani 1 1 d . . .
C5 C 0.0000 0.0258(5) 0.2500 0.0317(9) Uani 1 2 d S . .
H5A H -0.0588 -0.0163 0.2437 0.038 Uiso 0.50 1 d PR . .
H5B H 0.0459 -0.0163 0.3004 0.038 Uiso 0.50 1 d PR . .
H5C H 0.0129 -0.0163 0.2059 0.038 Uiso 0.50 1 d PR . .
C7 C 0.19795(18) 0.2153(4) 0.27417(15) 0.0247(6) Uani 1 1 d . . .
H7 H 0.1466 0.1713 0.2313 0.030 Uiso 1 1 calc R . .
C8 C 0.28130(18) 0.1931(4) 0.27330(16) 0.0267(6) Uani 1 1 d . . .
H8 H 0.2869 0.1330 0.2309 0.032 Uiso 1 1 calc R . .
C9 C 0.35616(18) 0.2596(4) 0.33502(16) 0.0281(6) Uani 1 1 d . . .
H9 H 0.4138 0.2449 0.3357 0.034 Uiso 1 1 calc R . .
C10 C 0.34590(18) 0.3475(4) 0.39560(16) 0.0254(6) Uani 1 1 d . . .
H10 H 0.3962 0.3967 0.4379 0.030 Uiso 1 1 calc R . .
C11 C 0.26081(17) 0.3628(3) 0.39367(15) 0.0202(5) Uani 1 1 d . . .
C12 C 0.24168(17) 0.4508(3) 0.45563(15) 0.0213(5) Uani 1 1 d . . .
C13 C 0.30728(18) 0.5194(4) 0.52406(15) 0.0259(6) Uani 1 1 d . . .
H13 H 0.3686 0.5110 0.5338 0.031 Uiso 1 1 calc R . .
C14 C 0.2821(2) 0.6005(4) 0.57829(16) 0.0295(6) Uani 1 1 d . . .
H14 H 0.3260 0.6482 0.6257 0.035 Uiso 1 1 calc R . .
C15 C 0.1928(2) 0.6112(4) 0.56267(16) 0.0292(6) Uani 1 1 d . . .
H15 H 0.1743 0.6666 0.5990 0.035 Uiso 1 1 calc R . .
C16 C 0.13068(19) 0.5400(4) 0.49323(17) 0.0289(6) Uani 1 1 d . . .
H16 H 0.0691 0.5476 0.4826 0.035 Uiso 1 1 calc R . .
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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
O4 Cu1 N17 174.00(6) . . ?
O4 Cu1 N6 94.30(6) . . ?
N17 Cu1 N6 79.70(9) . . ?
O4 Cu1 Cl2 92.66(4) . . ?
N17 Cu1 Cl2 92.24(6) . . ?
N6 Cu1 Cl2 141.68(6) . . ?
O4 Cu1 Cl3 80.90(7) . . ?
N17 Cu1 Cl3 100.02(7) . . ?
N6 Cu1 Cl3 102.20(6) . . ?
Cl2 Cu1 Cl3 116.10(2) . . ?
Cu1 Cl3 Cu1 80.01(3) 2 . ?
C5 O4 Cu1 120.91(7) . 2 ?
C5 O4 Cu1 120.91(7) . . ?
Cu1 O4 Cu1 118.19(13) 2 . ?
C7 N6 C11 119.0(2) . . ?
C7 N6 Cu1 126.16(18) . . ?
C11 N6 Cu1 114.86(17) . . ?
C16 N17 C12 118.5(2) . . ?
C16 N17 Cu1 125.12(18) . . ?
C12 N17 Cu1 116.07(18) . . ?
O4 C5 H5A 109.5 . . ?
O4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N6 C7 C8 122.0(3) . . ?
N6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C9 C8 C7 119.1(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 119.1(2) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 118.9(2) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
N6 C11 C10 121.8(2) . . ?
N6 C11 C12 114.3(2) . . ?
C10 C11 C12 123.9(2) . . ?
N17 C12 C13 121.8(2) . . ?
N17 C12 C11 114.7(2) . . ?
C13 C12 C11 123.5(2) . . ?
C12 C13 C14 118.9(2) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 119.3(3) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 118.9(3) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
N17 C16 C15 122.6(3) . . ?
N17 C16 H16 118.7 . . ?
C15 C16 H16 118.7 . . ?
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
Cu1 O4 1.9105(13) . ?
Cu1 N17 2.006(2) . ?
Cu1 N6 2.052(2) . ?
Cu1 Cl2 2.2917(7) . ?
Cu1 Cl3 2.5498(8) . ?
O4 C5 1.399(5) . ?
N6 C7 1.336(3) . ?
N6 C11 1.353(3) . ?
N17 C16 1.340(3) . ?
N17 C12 1.353(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9799 . ?
C7 C8 1.388(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.477(4) . ?
C12 C13 1.383(4) . ?
C13 C14 1.387(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.375(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 Cu1 Cl3 Cu1 0.0 . . . 2 ?
N17 Cu1 Cl3 Cu1 173.99(6) . . . 2 ?
N6 Cu1 Cl3 Cu1 92.47(6) . . . 2 ?
Cl2 Cu1 Cl3 Cu1 -88.50(3) . . . 2 ?
N6 Cu1 O4 C5 78.31(6) . . . . ?
Cl2 Cu1 O4 C5 -63.98(2) . . . . ?
Cl3 Cu1 O4 C5 180.0 . . . . ?
N6 Cu1 O4 Cu1 -101.69(6) . . . 2 ?
Cl2 Cu1 O4 Cu1 116.02(2) . . . 2 ?
Cl3 Cu1 O4 Cu1 0.0 . . . 2 ?
O4 Cu1 N6 C7 2.5(2) . . . . ?
N17 Cu1 N6 C7 -177.2(2) . . . . ?
Cl2 Cu1 N6 C7 102.3(2) . . . . ?
Cl3 Cu1 N6 C7 -79.1(2) . . . . ?
O4 Cu1 N6 C11 -176.93(18) . . . . ?
N17 Cu1 N6 C11 3.33(17) . . . . ?
Cl2 Cu1 N6 C11 -77.1(2) . . . . ?
Cl3 Cu1 N6 C11 101.47(17) . . . . ?
N6 Cu1 N17 C16 -179.0(2) . . . . ?
Cl2 Cu1 N17 C16 -36.7(2) . . . . ?
Cl3 Cu1 N17 C16 80.3(2) . . . . ?
N6 Cu1 N17 C12 -5.49(18) . . . . ?
Cl2 Cu1 N17 C12 136.78(18) . . . . ?
Cl3 Cu1 N17 C12 -106.22(18) . . . . ?
C11 N6 C7 C8 1.4(4) . . . . ?
Cu1 N6 C7 C8 -178.03(19) . . . . ?
N6 C7 C8 C9 -1.0(4) . . . . ?
C7 C8 C9 C10 -0.5(4) . . . . ?
C8 C9 C10 C11 1.6(4) . . . . ?
C7 N6 C11 C10 -0.2(4) . . . . ?
Cu1 N6 C11 C10 179.25(19) . . . . ?
C7 N6 C11 C12 179.7(2) . . . . ?
Cu1 N6 C11 C12 -0.8(3) . . . . ?
C9 C10 C11 N6 -1.3(4) . . . . ?
C9 C10 C11 C12 178.9(2) . . . . ?
C16 N17 C12 C13 0.2(4) . . . . ?
Cu1 N17 C12 C13 -173.7(2) . . . . ?
C16 N17 C12 C11 -179.4(2) . . . . ?
Cu1 N17 C12 C11 6.6(3) . . . . ?
N6 C11 C12 N17 -3.7(3) . . . . ?
C10 C11 C12 N17 176.2(2) . . . . ?
N6 C11 C12 C13 176.6(2) . . . . ?
C10 C11 C12 C13 -3.5(4) . . . . ?
N17 C12 C13 C14 0.0(4) . . . . ?
C11 C12 C13 C14 179.6(2) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C12 N17 C16 C15 -0.2(4) . . . . ?
Cu1 N17 C16 C15 173.1(2) . . . . ?
C14 C15 C16 N17 0.0(4) . . . . ?
