#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:40:15 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178958 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/87/4118793.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_4118793
loop_
_publ_author_name
'Raymond T. Gephart'
'Claire L. McMullin'
'Nicholas G. Sapiezynski'
'Eun Sil Jang'
'Mae Joanne B. Aguila'
'Thomas R. Cundari'
'Timothy H. Warren'
_publ_contact_author             'Timothy H. Warren'
_publ_contact_author_email       thw@georgetown.edu
_publ_section_title
;
 Reaction of CuIwith Dialkyl Peroxides: CuII-Alkoxides, Alkoxy Radicals,
 and Catalytic C-H Etherification
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17350
_journal_page_last               17353
_journal_paper_doi               10.1021/ja3053688
_journal_volume                  134
_journal_year                    2012
_chemical_formula_moiety         'C35 H35 Cl4 Cu N2 O2'
_chemical_formula_sum            'C35 H35 Cl4 Cu N2 O2'
_chemical_formula_weight         720.99
_chemical_name_common            '[Cl2NNCu]-OCMe2Ph'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 104.291(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.735(2)
_cell_length_b                   8.2314(11)
_cell_length_c                   27.148(4)
_cell_measurement_reflns_used    3364
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.021
_cell_measurement_theta_min      2.377
_cell_volume                     3407.4(8)
_computing_cell_refinement       'Bruker APEXII'
_computing_data_collection       'Bruker APEXII'
_computing_data_reduction        'Bruker APEXII'
_computing_molecular_graphics
'ORTEP-3 for Windows; Ferrugia L J (1997), J. Appl. Cryst. 30, 565'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'APEXII platform CCD, Bruker'
_diffrn_measurement_method       'omega 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  0.0747
_diffrn_reflns_av_sigmaI/netI    0.0745
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            27971
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    0.988
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6299
_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            brown
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       plate
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.857
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         7433
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0475
_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)+(0.0419P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0970
_reflns_number_gt                5038
_reflns_number_total             7433
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3053688_si_003.cif
_cod_data_source_block           cmpd_3
_cod_original_cell_volume        3407.5(8)
_cod_database_code               4118793
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cu1 Cu 0.01004(2) 0.17967(4) 0.140376(12) 0.01589(10) Uani 1 1 d .
Cl1 Cl -0.20404(5) 0.42364(9) 0.07491(3) 0.02426(18) Uani 1 1 d .
O1 O 0.01837(13) 0.1301(2) 0.20550(7) 0.0196(5) Uani 1 1 d .
N1 N -0.07693(14) 0.1504(3) 0.07918(8) 0.0141(5) Uani 1 1 d .
C1 C -0.06541(18) 0.1773(3) 0.03280(10) 0.0161(6) Uani 1 1 d .
Cl2 Cl -0.09968(5) -0.20173(9) 0.10083(3) 0.02556(18) Uani 1 1 d .
O2 O 0.04206(12) 0.0424(2) 0.50041(7) 0.0221(5) Uani 1 1 d .
N2 N 0.09539(15) 0.2689(3) 0.11050(8) 0.0164(5) Uani 1 1 d .
C2 C 0.01267(19) 0.2388(4) 0.02451(11) 0.0208(7) Uani 1 1 d .
H10 H 0.0148 0.2503 -0.0100 0.025 Uiso 1 1 calc R
Cl3 Cl 0.22257(5) 0.00353(10) 0.14992(3) 0.02936(19) Uani 1 1 d .
C3 C 0.08801(19) 0.2852(3) 0.06095(11) 0.0193(7) Uani 1 1 d .
Cl4 Cl 0.10515(6) 0.62134(10) 0.13999(3) 0.0362(2) Uani 1 1 d .
C4 C -0.13916(19) 0.1389(4) -0.01293(10) 0.0232(7) Uani 1 1 d .
H19A H -0.1618 0.0299 -0.0092 0.035 Uiso 1 1 calc R
H19B H -0.1173 0.1431 -0.0437 0.035 Uiso 1 1 calc R
H19C H -0.1863 0.2187 -0.0156 0.035 Uiso 1 1 calc R
C5 C 0.1637(2) 0.3549(4) 0.04316(12) 0.0297(8) Uani 1 1 d .
H33A H 0.1725 0.4687 0.0539 0.044 Uiso 1 1 calc R
H33B H 0.1510 0.3487 0.0060 0.044 Uiso 1 1 calc R
H33C H 0.2170 0.2928 0.0580 0.044 Uiso 1 1 calc R
C6 C -0.16121(18) 0.1055(3) 0.08485(10) 0.0154(6) Uani 1 1 d .
C7 C -0.22751(19) 0.2202(3) 0.08328(10) 0.0173(6) Uani 1 1 d .
C8 C -0.30946(19) 0.1785(4) 0.08922(11) 0.0233(7) Uani 1 1 d .
H13 H -0.3536 0.2589 0.0867 0.028 Uiso 1 1 calc R
C9 C -0.3263(2) 0.0192(4) 0.09885(12) 0.0269(8) Uani 1 1 d .
H30 H -0.3825 -0.0106 0.1030 0.032 Uiso 1 1 calc R
C10 C -0.2619(2) -0.0979(4) 0.10256(11) 0.0242(7) Uani 1 1 d .
H34 H -0.2734 -0.2076 0.1098 0.029 Uiso 1 1 calc R
C11 C -0.18082(19) -0.0543(4) 0.09574(11) 0.0184(6) Uani 1 1 d .
C12 C 0.17309(18) 0.3184(4) 0.14652(10) 0.0187(6) Uani 1 1 d .
C13 C 0.23747(19) 0.2053(4) 0.16893(11) 0.0204(7) Uani 1 1 d .
C14 C 0.3110(2) 0.2486(4) 0.20616(11) 0.0251(7) Uani 1 1 d .
H37 H 0.3539 0.1695 0.2205 0.030 Uiso 1 1 calc R
C15 C 0.3214(2) 0.4080(4) 0.22233(12) 0.0284(8) Uani 1 1 d .
H14 H 0.3718 0.4390 0.2478 0.034 Uiso 1 1 calc R
C16 C 0.2585(2) 0.5225(4) 0.20147(12) 0.0280(8) Uani 1 1 d .
H36 H 0.2655 0.6322 0.2126 0.034 Uiso 1 1 calc R
C17 C 0.18553(19) 0.4763(4) 0.16442(11) 0.0217(7) Uani 1 1 d .
C18 C -0.02523(19) 0.2070(4) 0.23852(11) 0.0204(7) Uani 1 1 d .
C19 C -0.0789(2) 0.3525(4) 0.21231(12) 0.0275(8) Uani 1 1 d .
H20A H -0.0393 0.4339 0.2039 0.041 Uiso 1 1 calc R
H20B H -0.1113 0.4006 0.2352 0.041 Uiso 1 1 calc R
H20C H -0.1203 0.3159 0.1811 0.041 Uiso 1 1 calc R
C20 C 0.0436(2) 0.2663(4) 0.28540(11) 0.0274(8) Uani 1 1 d .
H22A H 0.0755 0.1729 0.3034 0.041 Uiso 1 1 calc R
H22B H 0.0145 0.3248 0.3081 0.041 Uiso 1 1 calc R
H22C H 0.0849 0.3392 0.2747 0.041 Uiso 1 1 calc R
C21 C -0.08515(19) 0.0815(4) 0.25504(10) 0.0192(7) Uani 1 1 d .
C22 C -0.08605(19) -0.0788(4) 0.23904(11) 0.0216(7) Uani 1 1 d .
H27 H -0.0503 -0.1102 0.2171 0.026 Uiso 1 1 calc R
C23 C -0.1383(2) -0.1937(4) 0.25454(12) 0.0288(8) Uani 1 1 d .
H38 H -0.1379 -0.3028 0.2432 0.035 Uiso 1 1 calc R
C24 C -0.1910(2) -0.1514(4) 0.28620(12) 0.0300(8) Uani 1 1 d .
H39 H -0.2264 -0.2308 0.2969 0.036 Uiso 1 1 calc R
C25 C -0.1916(2) 0.0070(4) 0.30216(12) 0.0281(8) Uani 1 1 d .
H25 H -0.2278 0.0374 0.3239 0.034 Uiso 1 1 calc R
C26 C -0.13934(19) 0.1227(4) 0.28660(11) 0.0238(7) Uani 1 1 d .
H35 H -0.1407 0.2319 0.2977 0.029 Uiso 1 1 calc R
C27 C 0.04874(19) 0.0413(4) 0.44829(11) 0.0210(7) Uani 1 1 d .
C28 C -0.0272(2) 0.1361(4) 0.41560(11) 0.0246(7) Uani 1 1 d .
H28A H -0.0821 0.0771 0.4136 0.037 Uiso 1 1 calc R
H28B H -0.0182 0.1491 0.3814 0.037 Uiso 1 1 calc R
H28C H -0.0305 0.2433 0.4307 0.037 Uiso 1 1 calc R
C29 C 0.1355(2) 0.1299(4) 0.45225(12) 0.0254(7) Uani 1 1 d .
H11A H 0.1320 0.2392 0.4660 0.038 Uiso 1 1 calc R
H11B H 0.1469 0.1380 0.4184 0.038 Uiso 1 1 calc R
H11C H 0.1831 0.0695 0.4749 0.038 Uiso 1 1 calc R
C30 C 0.05728(19) -0.1329(4) 0.43103(11) 0.0191(7) Uani 1 1 d .
C31 C 0.0235(2) -0.1819(4) 0.38116(11) 0.0236(7) Uani 1 1 d .
H18 H -0.0093 -0.1075 0.3571 0.028 Uiso 1 1 calc R
C32 C 0.0372(2) -0.3392(4) 0.36622(12) 0.0266(7) Uani 1 1 d .
H12 H 0.0140 -0.3717 0.3320 0.032 Uiso 1 1 calc R
C33 C 0.0846(2) -0.4486(4) 0.40101(12) 0.0279(8) Uani 1 1 d .
H32 H 0.0944 -0.5558 0.3907 0.033 Uiso 1 1 calc R
C34 C 0.1175(2) -0.4009(4) 0.45095(12) 0.0275(8) Uani 1 1 d .
H29 H 0.1496 -0.4760 0.4751 0.033 Uiso 1 1 calc R
C35 C 0.1040(2) -0.2450(4) 0.46590(12) 0.0232(7) Uani 1 1 d .
H23 H 0.1268 -0.2135 0.5003 0.028 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'
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'
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_3
O1 Cu1 N2 129.03(9) .
O1 Cu1 N1 134.51(9) .
N2 Cu1 N1 96.32(10) .
C18 O1 Cu1 126.84(17) .
C1 N1 C6 119.6(2) .
C1 N1 Cu1 124.82(19) .
C6 N1 Cu1 115.52(17) .
N1 C1 C2 122.8(2) .
N1 C1 C4 119.1(2) .
C2 C1 C4 118.1(2) .
C27 O2 O2 105.1(2) 3_556
C3 N2 C12 120.8(2) .
C3 N2 Cu1 125.65(19) .
C12 N2 Cu1 113.53(17) .
C3 C2 C1 127.7(3) .
N2 C3 C2 122.4(3) .
N2 C3 C5 119.0(3) .
C2 C3 C5 118.5(3) .
C11 C6 C7 116.0(3) .
C11 C6 N1 121.8(3) .
C7 C6 N1 122.0(3) .
C8 C7 C6 122.6(3) .
C8 C7 Cl1 119.2(2) .
C6 C7 Cl1 118.2(2) .
C9 C8 C7 119.2(3) .
C8 C9 C10 120.4(3) .
C11 C10 C9 119.5(3) .
C10 C11 C6 122.1(3) .
C10 C11 Cl2 119.4(2) .
C6 C11 Cl2 118.4(2) .
C17 C12 C13 116.6(3) .
C17 C12 N2 122.2(3) .
C13 C12 N2 121.0(3) .
C14 C13 C12 122.1(3) .
C14 C13 Cl3 119.4(2) .
C12 C13 Cl3 118.5(2) .
C15 C14 C13 119.4(3) .
C14 C15 C16 120.1(3) .
C17 C16 C15 119.6(3) .
C16 C17 C12 122.3(3) .
C16 C17 Cl4 118.9(2) .
C12 C17 Cl4 118.8(2) .
O1 C18 C20 108.4(2) .
O1 C18 C19 110.8(2) .
C20 C18 C19 109.4(3) .
O1 C18 C21 108.3(2) .
C20 C18 C21 109.3(2) .
C19 C18 C21 110.6(2) .
C22 C21 C26 117.6(3) .
C22 C21 C18 120.5(3) .
C26 C21 C18 121.9(3) .
C23 C22 C21 121.0(3) .
C24 C23 C22 120.7(3) .
C25 C24 C23 119.2(3) .
C24 C25 C26 120.2(3) .
C25 C26 C21 121.2(3) .
O2 C27 C28 109.4(2) .
O2 C27 C30 109.9(2) .
C28 C27 C30 114.9(2) .
O2 C27 C29 102.0(2) .
C28 C27 C29 110.9(3) .
C30 C27 C29 109.0(2) .
C31 C30 C35 118.7(3) .
C31 C30 C27 122.2(3) .
C35 C30 C27 119.0(3) .
C30 C31 C32 120.4(3) .
C33 C32 C31 120.3(3) .
C32 C33 C34 119.5(3) .
C35 C34 C33 120.4(3) .
C34 C35 C30 120.7(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.7875(19) .
Cu1 N2 1.881(2) .
Cu1 N1 1.889(2) .
Cl1 C7 1.742(3) .
O1 C18 1.407(3) .
N1 C1 1.334(3) .
N1 C6 1.421(3) .
C1 C2 1.397(4) .
C1 C4 1.509(4) .
Cl2 C11 1.742(3) .
O2 C27 1.445(3) .
O2 O2 1.492(4) 3_556
N2 C3 1.328(3) .
N2 C12 1.424(3) .
C2 C3 1.397(4) .
Cl3 C13 1.738(3) .
C3 C5 1.505(4) .
Cl4 C17 1.746(3) .
C6 C11 1.400(4) .
C6 C7 1.400(4) .
C7 C8 1.382(4) .
C8 C9 1.375(4) .
C9 C10 1.385(4) .
C10 C11 1.381(4) .
C12 C17 1.384(4) .
C12 C13 1.400(4) .
C13 C14 1.381(4) .
C14 C15 1.380(4) .
C15 C16 1.383(5) .
C16 C17 1.380(4) .
C18 C20 1.533(4) .
C18 C19 1.535(4) .
C18 C21 1.538(4) .
C21 C22 1.388(4) .
C21 C26 1.392(4) .
C22 C23 1.386(4) .
C23 C24 1.377(4) .
C24 C25 1.375(4) .
C25 C26 1.391(4) .
C27 C28 1.517(4) .
C27 C30 1.524(4) .
C27 C29 1.528(4) .
C30 C31 1.387(4) .
C30 C35 1.395(4) .
C31 C32 1.389(4) .
C32 C33 1.382(4) .
C33 C34 1.383(4) .
C34 C35 1.378(4) .
