#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/00/40/7004024.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_7004024
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_sum            'C25 H20 Cl N7 O'
_chemical_formula_weight         469.93
_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                 97.61(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.644(5)
_cell_length_b                   8.9425(18)
_cell_length_c                   19.223(4)
_cell_measurement_reflns_used    17372
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      0.998
_cell_volume                     4539.8(16)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_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  0.0718
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            28018
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         3.25
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Mulabs, Platon'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5398
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0430
_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)+(0.0482P)²+3.2373P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1104
_reflns_number_gt                4085
_reflns_number_total             5398
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b802109k.txt
_cod_data_source_block           test
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7004024
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
Cl1 Cl 0.235078(16) 0.38201(4) 0.05416(2) 0.03178(12) Uani 1 1 d . . .
O20 O 0.26508(4) 0.87998(12) 0.14730(6) 0.0251(3) Uani 1 1 d . . .
N4 N 0.19930(5) 0.85768(14) 0.05810(7) 0.0197(3) Uani 1 1 d . . .
N2 N 0.18062(5) 0.61189(14) 0.01263(7) 0.0210(3) Uani 1 1 d . . .
N7 N 0.13109(5) 0.81511(14) -0.02645(7) 0.0202(3) Uani 1 1 d . . .
N6 N 0.25107(5) 0.65148(14) 0.10164(7) 0.0215(3) Uani 1 1 d . . .
C8 C 0.12186(5) 0.97445(16) -0.03017(8) 0.0197(3) Uani 1 1 d . . .
N24 N 0.32762(5) 1.21914(15) 0.26435(7) 0.0261(3) Uani 1 1 d . . .
C5 C 0.23680(5) 0.79532(16) 0.09985(8) 0.0192(3) Uani 1 1 d . . .
C3 C 0.17140(5) 0.75990(16) 0.01580(7) 0.0184(3) Uani 1 1 d . . .
C25 C 0.37255(6) 1.20021(18) 0.30399(8) 0.0233(3) Uani 1 1 d . . .
N29 N 0.45375(5) 1.28898(16) 0.35310(8) 0.0325(3) Uani 1 1 d . . .
C28 C 0.40971(6) 1.32282(19) 0.31395(8) 0.0246(3) Uani 1 1 d . . .
C15 C 0.05170(6) 0.67656(18) -0.04266(9) 0.0244(3) Uani 1 1 d . . .
H15A H 0.0448 0.7121 0.0016 0.029 Uiso 1 1 calc R . .
C14 C 0.09613(5) 0.71717(16) -0.06812(8) 0.0192(3) Uani 1 1 d . . .
C33 C 0.39940(7) 1.4639(2) 0.28518(9) 0.0316(4) Uani 1 1 d . . .
H33A H 0.3677 1.4843 0.2580 0.038 Uiso 1 1 calc R . .
N23 N 0.30425(5) 1.08557(16) 0.26667(7) 0.0262(3) Uani 1 1 d . . .
C1 C 0.22061(6) 0.57047(17) 0.05620(8) 0.0212(3) Uani 1 1 d . . .
C16 C 0.01749(6) 0.58335(18) -0.08266(9) 0.0275(4) Uani 1 1 d . . .
H16A H -0.0129 0.5549 -0.0655 0.033 Uiso 1 1 calc R . .
C12 C 0.12676(6) 1.20670(19) -0.09072(10) 0.0327(4) Uani 1 1 d . . .
H12A H 0.1343 1.2610 -0.1305 0.039 Uiso 1 1 calc R . .
C9 C 0.10248(7) 1.04711(19) 0.02372(9) 0.0303(4) Uani 1 1 d . . .
H9A H 0.0935 0.9922 0.0625 0.036 Uiso 1 1 calc R . .
C19 C 0.10652(6) 0.66580(18) -0.13254(8) 0.0248(3) Uani 1 1 d . . .
H19A H 0.1370 0.6936 -0.1496 0.030 Uiso 1 1 calc R . .
C18 C 0.07186(7) 0.57306(19) -0.17204(9) 0.0296(4) Uani 1 1 d . . .
H18A H 0.0787 0.5377 -0.2164 0.035 Uiso 1 1 calc R . .
C17 C 0.02733(6) 0.53182(18) -0.14713(9) 0.0284(4) Uani 1 1 d . . .
H17A H 0.0037 0.4684 -0.1743 0.034 Uiso 1 1 calc R . .
C13 C 0.13393(6) 1.05306(19) -0.08768(9) 0.0277(4) Uani 1 1 d . . .
H13A H 0.1470 1.0023 -0.1248 0.033 Uiso 1 1 calc R . .
C11 C 0.10869(7) 1.28089(19) -0.03632(10) 0.0336(4) Uani 1 1 d . . .
H11A H 0.1048 1.3865 -0.0379 0.040 Uiso 1 1 calc R . .
C27 C 0.33274(6) 0.9850(2) 0.30626(9) 0.0301(4) Uani 1 1 d . . .
H27A H 0.3238 0.8846 0.3150 0.036 Uiso 1 1 calc R . .
C10 C 0.09625(7) 1.2011(2) 0.02063(10) 0.0375(4) Uani 1 1 d . . .
H10A H 0.0834 1.2520 0.0578 0.045 Uiso 1 1 calc R . .
C30 C 0.48860(7) 1.3982(2) 0.36308(11) 0.0386(5) Uani 1 1 d . . .
H30A H 0.5201 1.3757 0.3903 0.046 Uiso 1 1 calc R . .
C21 C 0.25025(7) 1.03443(19) 0.15425(10) 0.0352(4) Uani 1 1 d . . .
H21A H 0.2154 1.0502 0.1304 0.042 Uiso 1 1 calc R . .
H21B H 0.2734 1.1013 0.1325 0.042 Uiso 1 1 calc R . .
C26 C 0.37722(6) 1.05506(19) 0.33155(9) 0.0285(4) Uani 1 1 d . . .
H26A H 0.4051 1.0141 0.3613 0.034 Uiso 1 1 calc R . .
C22 C 0.25278(6) 1.0686(2) 0.23152(10) 0.0357(4) Uani 1 1 d . . .
H22A H 0.2338 1.1620 0.2373 0.043 Uiso 1 1 calc R . .
H22B H 0.2360 0.9870 0.2544 0.043 Uiso 1 1 calc R . .
C31 C 0.48155(7) 1.5404(2) 0.33650(10) 0.0368(4) Uani 1 1 d . . .
H31A H 0.5074 1.6137 0.3453 0.044 Uiso 1 1 calc R . .
C32 C 0.43595(8) 1.5739(2) 0.29661(10) 0.0381(4) Uani 1 1 d . . .
H32A H 0.4298 1.6711 0.2774 0.046 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'
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
C5 O20 C21 117.82(12) . . ?
C5 N4 C3 113.91(13) . . ?
C1 N2 C3 112.56(12) . . ?
C3 N7 C14 121.04(12) . . ?
C3 N7 C8 120.40(12) . . ?
C14 N7 C8 118.55(11) . . ?
C1 N6 C5 111.14(13) . . ?
C9 C8 C13 120.69(15) . . ?
C9 C8 N7 120.33(14) . . ?
C13 C8 N7 118.95(14) . . ?
C25 N24 N23 104.49(13) . . ?
N4 C5 O20 119.22(13) . . ?
N4 C5 N6 127.62(13) . . ?
O20 C5 N6 113.16(12) . . ?
N4 C3 N2 125.06(13) . . ?
N4 C3 N7 117.15(13) . . ?
N2 C3 N7 117.79(13) . . ?
N24 C25 C26 111.07(14) . . ?
N24 C25 C28 120.91(15) . . ?
C26 C25 C28 128.02(15) . . ?
C28 N29 C30 116.90(16) . . ?
N29 C28 C33 122.66(15) . . ?
N29 C28 C25 115.34(15) . . ?
C33 C28 C25 122.00(15) . . ?
C14 C15 C16 119.30(15) . . ?
C14 C15 H15A 120.3 . . ?
C16 C15 H15A 120.3 . . ?
C19 C14 C15 120.68(14) . . ?
C19 C14 N7 120.54(14) . . ?
C15 C14 N7 118.79(14) . . ?
C32 C33 C28 119.03(16) . . ?
C32 C33 H33A 120.5 . . ?
C28 C33 H33A 120.5 . . ?
C27 N23 N24 112.44(13) . . ?
C27 N23 C22 128.30(15) . . ?
N24 N23 C22 119.17(14) . . ?
N2 C1 N6 129.62(14) . . ?
N2 C1 Cl1 115.03(11) . . ?
N6 C1 Cl1 115.35(11) . . ?
C17 C16 C15 120.57(15) . . ?
C17 C16 H16A 119.7 . . ?
C15 C16 H16A 119.7 . . ?
C11 C12 C13 120.32(16) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C8 C9 C10 119.34(16) . . ?
C8 C9 H9A 120.3 . . ?
C10 C9 H9A 120.3 . . ?
C14 C19 C18 119.35(15) . . ?
C14 C19 H19A 120.3 . . ?
C18 C19 H19A 120.3 . . ?
C17 C18 C19 120.47(16) . . ?
C17 C18 H18A 119.8 . . ?
C19 C18 H18A 119.8 . . ?
C16 C17 C18 119.63(15) . . ?
C16 C17 H17A 120.2 . . ?
C18 C17 H17A 120.2 . . ?
C8 C13 C12 119.44(16) . . ?
C8 C13 H13A 120.3 . . ?
C12 C13 H13A 120.3 . . ?
C12 C11 C10 119.78(16) . . ?
C12 C11 H11A 120.1 . . ?
C10 C11 H11A 120.1 . . ?
N23 C27 C26 106.93(15) . . ?
N23 C27 H27A 126.5 . . ?
C26 C27 H27A 126.5 . . ?
C11 C10 C9 120.40(17) . . ?
C11 C10 H10A 119.8 . . ?
C9 C10 H10A 119.8 . . ?
N29 C30 C31 124.18(17) . . ?
N29 C30 H30A 117.9 . . ?
C31 C30 H30A 117.9 . . ?
O20 C21 C22 107.89(14) . . ?
O20 C21 H21A 110.1 . . ?
C22 C21 H21A 110.1 . . ?
O20 C21 H21B 110.1 . . ?
C22 C21 H21B 110.1 . . ?
H21A C21 H21B 108.4 . . ?
C27 C26 C25 105.08(15) . . ?
C27 C26 H26A 127.5 . . ?
C25 C26 H26A 127.5 . . ?
N23 C22 C21 113.25(15) . . ?
N23 C22 H22A 108.9 . . ?
C21 C22 H22A 108.9 . . ?
N23 C22 H22B 108.9 . . ?
C21 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
C30 C31 C32 118.33(16) . . ?
C30 C31 H31A 120.8 . . ?
C32 C31 H31A 120.8 . . ?
C31 C32 C33 118.89(18) . . ?
C31 C32 H32A 120.6 . . ?
C33 C32 H32A 120.6 . . ?
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
Cl1 C1 1.7305(16) . ?
O20 C5 1.3382(18) . ?
O20 C21 1.448(2) . ?
N4 C5 1.3195(19) . ?
N4 C3 1.3483(19) . ?
N2 C1 1.3181(19) . ?
N2 C3 1.3490(19) . ?
N7 C3 1.3513(18) . ?
N7 C14 1.4418(18) . ?
N7 C8 1.4462(19) . ?
N6 C1 1.326(2) . ?
N6 C5 1.3405(19) . ?
C8 C9 1.380(2) . ?
C8 C13 1.384(2) . ?
N24 C25 1.342(2) . ?
N24 N23 1.3505(19) . ?
C25 C26 1.401(2) . ?
C25 C28 1.473(2) . ?
N29 C28 1.342(2) . ?
N29 C30 1.344(2) . ?
C28 C33 1.390(2) . ?
C15 C14 1.388(2) . ?
C15 C16 1.390(2) . ?
C15 H15A 0.9500 . ?
C14 C19 1.383(2) . ?
C33 C32 1.382(2) . ?
C33 H33A 0.9500 . ?
N23 C27 1.346(2) . ?
N23 C22 1.454(2) . ?
C16 C17 1.380(2) . ?
C16 H16A 0.9500 . ?
C12 C11 1.378(3) . ?
C12 C13 1.387(2) . ?
C12 H12A 0.9500 . ?
C9 C10 1.387(2) . ?
C9 H9A 0.9500 . ?
C19 C18 1.390(2) . ?
C19 H19A 0.9500 . ?
C18 C17 1.387(2) . ?
C18 H18A 0.9500 . ?
C17 H17A 0.9500 . ?
C13 H13A 0.9500 . ?
C11 C10 1.383(3) . ?
C11 H11A 0.9500 . ?
C27 C26 1.371(2) . ?
C27 H27A 0.9500 . ?
C10 H10A 0.9500 . ?
C30 C31 1.374(3) . ?
C30 H30A 0.9500 . ?
C21 C22 1.509(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C26 H26A 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C31 C32 1.381(3) . ?
C31 H31A 0.9500 . ?
C32 H32A 0.9500 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25935173
