#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/00/40/7004025.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_7004025
loop_
_publ_author_name
'Lu, Zhengliang'
'Costa, José Sánchez'
'Roubeau, Olivier'
'Mutikainen, Ilpo'
'Turpeinen, Urho'
'Teat, Simon J.'
'Gamez, Patrick'
'Reedijk, Jan'
_publ_section_title
;
 A copper complex bearing a TEMPO moiety as catalyst for the aerobic
 oxidation of primary alcohols
;
_journal_issue                   27
_journal_name_full               'Dalton Transactions'
_journal_page_first              3567
_journal_page_last               3573
_journal_paper_doi               10.1039/b802109k
_journal_year                    2008
_chemical_formula_moiety         'C25 H20 Cl N7 O'
_chemical_formula_sum            'C25 H20 Cl N7 O'
_chemical_formula_weight         469.93
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.31(3)
_cell_angle_beta                 93.73(3)
_cell_angle_gamma                102.40(3)
_cell_formula_units_Z            2
_cell_length_a                   8.500(2)
_cell_length_b                   9.483(2)
_cell_length_c                   15.043(3)
_cell_measurement_reflns_used    42
_cell_measurement_temperature    373(2)
_cell_measurement_theta_max      14.56
_cell_measurement_theta_min      4.22
_cell_volume                     1162.4(5)
_computing_cell_refinement       'DirAx (Duisenberg 1992)'
_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_data_reduction        'COLLECT/EVAL (Nonius, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1990)'
_computing_publication_material  'SHELXTL (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      373(2)
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       ω-scan
_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  0.1386
_diffrn_reflns_av_sigmaI/netI    0.3327
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11933
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         2.83
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.9863
_exptl_absorpt_correction_T_min  0.9616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.904
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4212
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.904
_refine_ls_R_factor_all          0.2916
_refine_ls_R_factor_gt           0.0642
_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)+(0.0803P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1931
_reflns_number_gt                1382
_reflns_number_total             4212
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b802109k.txt
_cod_data_source_block           zl002
_cod_original_cell_volume        1162.4(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7004025
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
N1 N 1.0862(5) 0.4912(4) 0.3603(3) 0.0306(12) Uani 1 1 d . . .
C2 C 1.1211(6) 0.3451(6) 0.3374(4) 0.0347(15) Uani 1 1 d . . .
C3 C 1.2224(6) 0.3206(6) 0.2712(4) 0.0402(16) Uani 1 1 d . . .
H3A H 1.2720 0.3967 0.2433 0.048 Uiso 1 1 calc R . .
C4 C 1.2490(6) 0.1791(7) 0.2467(4) 0.0438(17) Uani 1 1 d . . .
H4A H 1.3182 0.1617 0.2029 0.053 Uiso 1 1 calc R . .
C5 C 1.1737(7) 0.0654(6) 0.2870(4) 0.0447(17) Uani 1 1 d . . .
H5A H 1.1886 -0.0288 0.2686 0.054 Uiso 1 1 calc R . .
C6 C 1.0747(7) 0.0922(6) 0.3558(4) 0.0465(17) Uani 1 1 d . . .
H6A H 1.0265 0.0169 0.3847 0.056 Uiso 1 1 calc R . .
C7 C 1.0495(7) 0.2328(7) 0.3803(4) 0.0458(17) Uani 1 1 d . . .
H7A H 0.9839 0.2516 0.4259 0.055 Uiso 1 1 calc R . .
C8 C 1.1961(6) 0.6044(6) 0.4266(4) 0.0331(15) Uani 1 1 d . . .
C9 C 1.2921(6) 0.5612(6) 0.4921(4) 0.0369(16) Uani 1 1 d . . .
H9A H 1.2856 0.4621 0.4923 0.044 Uiso 1 1 calc R . .
C10 C 1.3987(7) 0.6688(7) 0.5579(4) 0.0444(17) Uani 1 1 d . . .
H10A H 1.4625 0.6398 0.6009 0.053 Uiso 1 1 calc R . .
C11 C 1.4093(7) 0.8169(7) 0.5590(4) 0.0499(18) Uani 1 1 d . . .
H11A H 1.4756 0.8872 0.6041 0.060 Uiso 1 1 calc R . .
C12 C 1.3193(7) 0.8586(7) 0.4917(5) 0.0439(17) Uani 1 1 d . . .
H12A H 1.3289 0.9579 0.4909 0.053 Uiso 1 1 calc R . .
C13 C 1.2144(6) 0.7546(6) 0.4250(4) 0.0349(15) Uani 1 1 d . . .
H13A H 1.1569 0.7850 0.3798 0.042 Uiso 1 1 calc R . .
C14 C 0.9369(6) 0.5038(6) 0.3241(4) 0.0318(15) Uani 1 1 d . . .
N15 N 0.8823(5) 0.6272(5) 0.3558(3) 0.0366(13) Uani 1 1 d . . .
C16 C 0.7335(7) 0.6191(6) 0.3159(4) 0.0348(15) Uani 1 1 d . . .
N17 N 0.6384(5) 0.5143(5) 0.2519(3) 0.0371(13) Uani 1 1 d . . .
C18 C 0.7113(7) 0.4028(6) 0.2255(4) 0.0344(15) Uani 1 1 d . . .
N19 N 0.8544(6) 0.3897(5) 0.2585(3) 0.0336(12) Uani 1 1 d . . .
Cl20 Cl 0.65393(18) 0.76988(17) 0.35693(11) 0.0591(6) Uani 1 1 d . . .
O21 O 0.6212(4) 0.2955(4) 0.1605(3) 0.0408(11) Uani 1 1 d . . .
C22 C 0.6958(6) 0.1741(5) 0.1266(4) 0.0372(16) Uani 1 1 d . . .
H22B H 0.6123 0.0901 0.0966 0.045 Uiso 1 1 calc R . .
H22A H 0.7508 0.1456 0.1770 0.045 Uiso 1 1 calc R . .
C23 C 0.8171(6) 0.2200(6) 0.0599(4) 0.0390(16) Uani 1 1 d . . .
H23A H 0.8933 0.3103 0.0881 0.047 Uiso 1 1 calc R . .
H23B H 0.8777 0.1448 0.0459 0.047 Uiso 1 1 calc R . .
N24 N 0.7360(5) 0.2425(5) -0.0251(3) 0.0328(12) Uani 1 1 d . . .
N25 N 0.6655(6) 0.1170(5) -0.0890(4) 0.0450(14) Uani 1 1 d . . .
C26 C 0.5941(7) 0.1672(7) -0.1551(4) 0.0463(18) Uani 1 1 d . . .
H26A H 0.5374 0.1079 -0.2077 0.056 Uiso 1 1 calc R . .
C27 C 0.6146(7) 0.3202(7) -0.1358(4) 0.0400(16) Uani 1 1 d . . .
H27A H 0.5754 0.3780 -0.1722 0.048 Uiso 1 1 calc R . .
C28 C 0.7053(6) 0.3691(6) -0.0510(4) 0.0312(15) Uani 1 1 d . . .
C29 C 0.7589(7) 0.5204(6) 0.0007(4) 0.0358(16) Uani 1 1 d . . .
N30 N 0.8732(6) 0.5496(5) 0.0726(3) 0.0412(14) Uani 1 1 d . . .
C31 C 0.9225(6) 0.6905(7) 0.1169(4) 0.0419(16) Uani 1 1 d . . .
H31A H 1.0000 0.7111 0.1666 0.050 Uiso 1 1 calc R . .
C32 C 0.8628(7) 0.8074(6) 0.0917(5) 0.0460(17) Uani 1 1 d . . .
H32A H 0.9015 0.9030 0.1230 0.055 Uiso 1 1 calc R . .
C33 C 0.7445(8) 0.7758(7) 0.0187(4) 0.0520(19) Uani 1 1 d . . .
H33A H 0.7006 0.8498 0.0008 0.062 Uiso 1 1 calc R . .
C34 C 0.6925(7) 0.6316(6) -0.0272(4) 0.0419(17) Uani 1 1 d . . .
H34A H 0.6138 0.6088 -0.0764 0.050 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'
Cl Cl 0.1484 0.1585 '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
C14 N1 C8 124.5(4) . . ?
C14 N1 C2 115.4(4) . . ?
C8 N1 C2 119.6(4) . . ?
C7 C2 C3 120.7(5) . . ?
C7 C2 N1 120.0(5) . . ?
C3 C2 N1 119.3(5) . . ?
C2 C3 C4 119.0(5) . . ?
C2 C3 H3A 120.5 . . ?
C4 C3 H3A 120.5 . . ?
C5 C4 C3 120.7(5) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 119.9(5) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C7 C6 C5 119.2(6) . . ?
C7 C6 H6A 120.4 . . ?
C5 C6 H6A 120.4 . . ?
C2 C7 C6 120.5(5) . . ?
C2 C7 H7A 119.7 . . ?
C6 C7 H7A 119.7 . . ?
C13 C8 C9 118.9(5) . . ?
C13 C8 N1 122.4(5) . . ?
C9 C8 N1 118.7(5) . . ?
C8 C9 C10 119.9(5) . . ?
C8 C9 H9A 120.1 . . ?
C10 C9 H9A 120.1 . . ?
C11 C10 C9 120.8(6) . . ?
C11 C10 H10A 119.6 . . ?
C9 C10 H10A 119.6 . . ?
C12 C11 C10 118.9(6) . . ?
C12 C11 H11A 120.5 . . ?
C10 C11 H11A 120.5 . . ?
C11 C12 C13 121.5(6) . . ?
C11 C12 H12A 119.3 . . ?
C13 C12 H12A 119.3 . . ?
C12 C13 C8 119.9(6) . . ?
C12 C13 H13A 120.1 . . ?
C8 C13 H13A 120.1 . . ?
N19 C14 N15 125.0(5) . . ?
N19 C14 N1 116.3(5) . . ?
N15 C14 N1 118.7(5) . . ?
C16 N15 C14 110.9(5) . . ?
N15 C16 N17 130.4(5) . . ?
N15 C16 Cl20 113.1(4) . . ?
N17 C16 Cl20 116.5(4) . . ?
C16 N17 C18 111.6(5) . . ?
N19 C18 N17 126.6(5) . . ?
N19 C18 O21 119.5(5) . . ?
N17 C18 O21 113.8(5) . . ?
C18 N19 C14 115.4(5) . . ?
C18 O21 C22 116.5(4) . . ?
O21 C22 C23 110.4(4) . . ?
O21 C22 H22B 109.6 . . ?
C23 C22 H22B 109.6 . . ?
O21 C22 H22A 109.6 . . ?
C23 C22 H22A 109.6 . . ?
H22B C22 H22A 108.1 . . ?
N24 C23 C22 111.9(4) . . ?
N24 C23 H23A 109.2 . . ?
C22 C23 H23A 109.2 . . ?
N24 C23 H23B 109.2 . . ?
C22 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C28 N24 N25 112.1(5) . . ?
C28 N24 C23 130.8(5) . . ?
N25 N24 C23 116.9(5) . . ?
C26 N25 N24 104.4(5) . . ?
N25 C26 C27 112.0(6) . . ?
N25 C26 H26A 124.0 . . ?
C27 C26 H26A 124.0 . . ?
C26 C27 C28 106.9(5) . . ?
C26 C27 H27A 126.6 . . ?
C28 C27 H27A 126.6 . . ?
N24 C28 C27 104.6(5) . . ?
N24 C28 C29 126.7(5) . . ?
C27 C28 C29 128.7(5) . . ?
N30 C29 C34 121.5(5) . . ?
N30 C29 C28 119.5(5) . . ?
C34 C29 C28 119.0(6) . . ?
C31 N30 C29 117.8(5) . . ?
N30 C31 C32 123.6(6) . . ?
N30 C31 H31A 118.2 . . ?
C32 C31 H31A 118.2 . . ?
C33 C32 C31 118.0(6) . . ?
C33 C32 H32A 121.0 . . ?
C31 C32 H32A 121.0 . . ?
C32 C33 C34 119.0(6) . . ?
C32 C33 H33A 120.5 . . ?
C34 C33 H33A 120.5 . . ?
C33 C34 C29 120.1(6) . . ?
C33 C34 H34A 119.9 . . ?
C29 C34 H34A 119.9 . . ?
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
N1 C14 1.385(6) . ?
N1 C8 1.456(6) . ?
N1 C2 1.470(6) . ?
C2 C7 1.384(7) . ?
C2 C3 1.382(6) . ?
C3 C4 1.404(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.380(7) . ?
C4 H4A 0.9300 . ?
C5 C6 1.401(7) . ?
C5 H5A 0.9300 . ?
C6 C7 1.391(7) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 C13 1.404(7) . ?
C8 C9 1.405(7) . ?
C9 C10 1.414(7) . ?
C9 H9A 0.9300 . ?
C10 C11 1.385(7) . ?
C10 H10A 0.9300 . ?
C11 C12 1.387(7) . ?
C11 H11A 0.9300 . ?
C12 C13 1.400(7) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 N19 1.368(6) . ?
C14 N15 1.377(6) . ?
N15 C16 1.345(6) . ?
C16 N17 1.346(6) . ?
C16 Cl20 1.751(5) . ?
N17 C18 1.355(6) . ?
C18 N19 1.323(6) . ?
C18 O21 1.350(6) . ?
O21 C22 1.467(5) . ?
C22 C23 1.531(6) . ?
C22 H22B 0.9700 . ?
C22 H22A 0.9700 . ?
C23 N24 1.482(6) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
N24 C28 1.390(6) . ?
N24 N25 1.395(5) . ?
N25 C26 1.335(6) . ?
C26 C27 1.402(7) . ?
C26 H26A 0.9300 . ?
C27 C28 1.401(7) . ?
C27 H27A 0.9300 . ?
C28 C29 1.477(7) . ?
C29 N30 1.358(6) . ?
C29 C34 1.404(7) . ?
N30 C31 1.357(6) . ?
C31 C32 1.408(7) . ?
C31 H31A 0.9300 . ?
C32 C33 1.388(7) . ?
C32 H32A 0.9300 . ?
C33 C34 1.392(7) . ?
C33 H33A 0.9300 . ?
C34 H34A 0.9300 . ?
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
C14 N1 C2 C7 -76.3(6) . . . . ?
C8 N1 C2 C7 95.9(6) . . . . ?
C14 N1 C2 C3 102.0(6) . . . . ?
C8 N1 C2 C3 -85.8(6) . . . . ?
C7 C2 C3 C4 1.3(8) . . . . ?
N1 C2 C3 C4 -177.0(5) . . . . ?
C2 C3 C4 C5 0.9(8) . . . . ?
C3 C4 C5 C6 -2.7(9) . . . . ?
C4 C5 C6 C7 2.2(8) . . . . ?
C3 C2 C7 C6 -1.7(8) . . . . ?
N1 C2 C7 C6 176.6(5) . . . . ?
C5 C6 C7 C2 0.0(8) . . . . ?
C14 N1 C8 C13 -36.4(7) . . . . ?
C2 N1 C8 C13 152.2(5) . . . . ?
C14 N1 C8 C9 146.3(5) . . . . ?
C2 N1 C8 C9 -25.2(7) . . . . ?
C13 C8 C9 C10 3.2(7) . . . . ?
N1 C8 C9 C10 -179.3(4) . . . . ?
C8 C9 C10 C11 0.4(8) . . . . ?
C9 C10 C11 C12 -3.1(8) . . . . ?
C10 C11 C12 C13 2.2(8) . . . . ?
C11 C12 C13 C8 1.4(8) . . . . ?
C9 C8 C13 C12 -4.1(7) . . . . ?
N1 C8 C13 C12 178.6(4) . . . . ?
C8 N1 C14 N19 176.2(4) . . . . ?
C2 N1 C14 N19 -12.0(7) . . . . ?
C8 N1 C14 N15 -4.0(7) . . . . ?
C2 N1 C14 N15 167.8(4) . . . . ?
N19 C14 N15 C16 2.0(7) . . . . ?
N1 C14 N15 C16 -177.8(5) . . . . ?
C14 N15 C16 N17 -1.3(8) . . . . ?
C14 N15 C16 Cl20 177.5(3) . . . . ?
N15 C16 N17 C18 -0.9(8) . . . . ?
Cl20 C16 N17 C18 -179.6(4) . . . . ?
C16 N17 C18 N19 2.7(7) . . . . ?
C16 N17 C18 O21 -179.2(5) . . . . ?
N17 C18 N19 C14 -2.1(8) . . . . ?
O21 C18 N19 C14 179.9(4) . . . . ?
N15 C14 N19 C18 -0.6(7) . . . . ?
N1 C14 N19 C18 179.2(4) . . . . ?
N19 C18 O21 C22 -3.9(7) . . . . ?
N17 C18 O21 C22 177.9(4) . . . . ?
C18 O21 C22 C23 -78.1(6) . . . . ?
O21 C22 C23 N24 -68.1(5) . . . . ?
C22 C23 N24 C28 94.4(6) . . . . ?
C22 C23 N24 N25 -79.8(5) . . . . ?
C28 N24 N25 C26 1.2(5) . . . . ?
C23 N24 N25 C26 176.4(4) . . . . ?
N24 N25 C26 C27 -0.5(6) . . . . ?
N25 C26 C27 C28 -0.2(6) . . . . ?
N25 N24 C28 C27 -1.3(5) . . . . ?
C23 N24 C28 C27 -175.7(4) . . . . ?
N25 N24 C28 C29 179.0(4) . . . . ?
C23 N24 C28 C29 4.6(8) . . . . ?
C26 C27 C28 N24 0.9(5) . . . . ?
C26 C27 C28 C29 -179.4(5) . . . . ?
N24 C28 C29 N30 13.1(7) . . . . ?
C27 C28 C29 N30 -166.5(5) . . . . ?
N24 C28 C29 C34 -168.3(5) . . . . ?
C27 C28 C29 C34 12.1(8) . . . . ?
C34 C29 N30 C31 -0.3(7) . . . . ?
C28 C29 N30 C31 178.3(4) . . . . ?
C29 N30 C31 C32 -0.7(7) . . . . ?
N30 C31 C32 C33 1.5(8) . . . . ?
C31 C32 C33 C34 -1.2(8) . . . . ?
C32 C33 C34 C29 0.3(8) . . . . ?
N30 C29 C34 C33 0.5(8) . . . . ?
C28 C29 C34 C33 -178.1(5) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25935174
