#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/00/11/7001160.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_7001160
loop_
_publ_author_name
'Lu, Zhengliang'
'Ladrak, Tim'
'Roubeau, Olivier'
'van der Toorn, John'
'Teat, Simon J.'
'Massera, Chiara'
'Gamez, Patrick'
'Reedijk, Jan'
_publ_section_title
;
 Selective, catalytic aerobic oxidation of alcohols using CuBr2 and
 bifunctional triazine-based ligands containing both a bipyridine and a
 TEMPO group
;
_journal_issue                   18
_journal_name_full               'Dalton Transactions'
_journal_page_first              3559
_journal_page_last               3570
_journal_paper_doi               10.1039/b820554j
_journal_year                    2009
_chemical_formula_sum            'C28 H23 Cl N6 O'
_chemical_formula_weight         494.97
_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                75.296(2)
_cell_angle_beta                 78.660(2)
_cell_angle_gamma                70.606(2)
_cell_formula_units_Z            2
_cell_length_a                   9.8067(8)
_cell_length_b                   10.8773(9)
_cell_length_c                   12.7401(11)
_cell_measurement_reflns_used    7095
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.04
_cell_measurement_theta_min      1.67
_cell_volume                     1230.46(18)
_computing_data_collection       SMART
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Giacovazzo et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean '8.192 pixels/mm'
_diffrn_measured_fraction_theta_full 0.912
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device_type  'Bruker AXS Smart 1000'
_diffrn_measurement_method       omega-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15197
_diffrn_reflns_theta_full        29.04
_diffrn_reflns_theta_max         29.04
_diffrn_reflns_theta_min         1.67
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  1.0000000
_exptl_absorpt_correction_T_min  0.654762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER AXS SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         6001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0860P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1460
_reflns_number_gt                3730
_reflns_number_total             6001
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b820554j.txt
_cod_data_source_block           zl08
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7001160
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 -0.07093(15) 0.34929(15) 0.74758(11) 0.0668(4) Uani 1 1 d . . .
N2 N 0.04750(14) 0.26058(13) 0.90869(10) 0.0604(3) Uani 1 1 d . . .
N3 N 0.11137(13) 0.43572(13) 0.77284(10) 0.0574(3) Uani 1 1 d . . .
N4 N 0.21902(14) 0.35217(13) 0.93127(10) 0.0572(3) Uani 1 1 d . . .
N5 N 0.45171(17) 0.76003(15) 0.36543(11) 0.0701(4) Uani 1 1 d . . .
N6 N 0.67661(17) 0.87187(16) 0.48968(12) 0.0741(4) Uani 1 1 d . . .
O1 O -0.01185(12) 0.51400(12) 0.62254(9) 0.0718(3) Uani 1 1 d . . .
Cl1 Cl -0.14493(6) 0.15765(6) 0.88668(4) 0.0873(2) Uani 1 1 d . . .
C1 C -0.04456(17) 0.26901(17) 0.84208(14) 0.0621(4) Uani 1 1 d . . .
C2 C 0.01274(17) 0.43100(16) 0.71766(13) 0.0594(4) Uani 1 1 d . . .
C3 C 0.12344(16) 0.34911(15) 0.86857(12) 0.0538(3) Uani 1 1 d . . .
C4 C 0.24525(16) 0.26201(15) 1.03451(12) 0.0551(4) Uani 1 1 d . . .
C5 C 0.30818(19) 0.12736(18) 1.04053(16) 0.0688(4) Uani 1 1 d . . .
C6 C 0.3408(2) 0.0451(2) 1.14071(17) 0.0759(5) Uani 1 1 d . . .
C7 C 0.31171(19) 0.0966(2) 1.23299(16) 0.0747(5) Uani 1 1 d . . .
C8 C 0.2479(2) 0.2301(2) 1.22719(15) 0.0728(5) Uani 1 1 d . . .
C9 C 0.21432(18) 0.3130(2) 1.12806(13) 0.0628(4) Uani 1 1 d . . .
C10 C 0.29238(16) 0.45347(16) 0.90040(12) 0.0546(4) Uani 1 1 d . . .
C11 C 0.2144(2) 0.58339(18) 0.90396(14) 0.0667(4) Uani 1 1 d . . .
C12 C 0.2861(3) 0.6787(2) 0.88155(15) 0.0786(5) Uani 1 1 d . . .
C13 C 0.4345(3) 0.6431(2) 0.85622(15) 0.0825(6) Uani 1 1 d . . .
C14 C 0.5120(2) 0.5146(3) 0.85174(16) 0.0815(6) Uani 1 1 d . . .
C15 C 0.44060(19) 0.4178(2) 0.87375(14) 0.0674(4) Uani 1 1 d . . .
C16 C 0.07408(19) 0.60731(18) 0.58166(16) 0.0681(4) Uani 1 1 d . . .
C17 C 0.2227(2) 0.53929(19) 0.52949(15) 0.0678(4) Uani 1 1 d . . .
C18 C 0.31945(18) 0.62908(17) 0.50120(13) 0.0622(4) Uani 1 1 d . . .
C19 C 0.3583(2) 0.68829(19) 0.39497(14) 0.0717(5) Uani 1 1 d . . .
C20 C 0.47250(19) 0.72846(19) 0.55358(14) 0.0678(4) Uani 1 1 d . . .
C21 C 0.51063(17) 0.77786(15) 0.44490(12) 0.0569(4) Uani 1 1 d . . .
C22 C 0.3778(2) 0.6538(2) 0.58172(14) 0.0707(5) Uani 1 1 d . . .
C23 C 0.62145(16) 0.85008(15) 0.41001(12) 0.0575(4) Uani 1 1 d . . .
C24 C 0.66843(19) 0.89030(17) 0.30096(14) 0.0644(4) Uani 1 1 d . . .
C25 C 0.7732(2) 0.95507(19) 0.27283(16) 0.0706(4) Uani 1 1 d . . .
C26 C 0.83128(19) 0.97942(18) 0.35258(16) 0.0712(5) Uani 1 1 d . . .
C27 C 0.7778(2) 0.9353(2) 0.45897(17) 0.0785(5) Uani 1 1 d . . .
C28 C 0.9476(3) 1.0485(3) 0.3271(2) 0.0989(7) Uani 1 1 d . . .
H28A H 1.0381 0.9855 0.3475 0.155(6) Uiso 1 1 calc R . .
H28B H 0.9198 1.1185 0.3673 0.155(6) Uiso 1 1 calc R . .
H28C H 0.9590 1.0856 0.2502 0.155(6) Uiso 1 1 calc R . .
H5 H 0.3264(19) 0.0932(17) 0.9768(14) 0.068(5) Uiso 1 1 d . . .
H6 H 0.385(2) -0.040(2) 1.1447(17) 0.088(6) Uiso 1 1 d . . .
H7 H 0.337(2) 0.038(2) 1.3014(17) 0.086(6) Uiso 1 1 d . . .
H8 H 0.229(2) 0.267(2) 1.2870(18) 0.096(7) Uiso 1 1 d . . .
H9 H 0.170(2) 0.3993(19) 1.1240(14) 0.072(5) Uiso 1 1 d . . .
H11 H 0.115(2) 0.6077(19) 0.9201(15) 0.081(6) Uiso 1 1 d . . .
H12 H 0.224(2) 0.769(2) 0.8868(16) 0.090(6) Uiso 1 1 d . . .
H13 H 0.485(2) 0.709(2) 0.8404(15) 0.086(6) Uiso 1 1 d . . .
H14 H 0.617(3) 0.485(2) 0.8315(18) 0.106(7) Uiso 1 1 d . . .
H15 H 0.495(2) 0.324(2) 0.8674(15) 0.081(6) Uiso 1 1 d . . .
H16A H 0.0210(19) 0.6775(18) 0.5254(15) 0.071(5) Uiso 1 1 d . . .
H16B H 0.0799(19) 0.6447(17) 0.6468(15) 0.074(5) Uiso 1 1 d . . .
H17A H 0.2696(19) 0.4537(18) 0.5819(14) 0.068(5) Uiso 1 1 d . . .
H17B H 0.218(2) 0.5080(18) 0.4629(16) 0.078(5) Uiso 1 1 d . . .
H19 H 0.317(2) 0.6710(19) 0.3383(16) 0.086(6) Uiso 1 1 d . . .
H20 H 0.513(2) 0.745(2) 0.6083(18) 0.102(7) Uiso 1 1 d . . .
H22 H 0.3530(19) 0.6178(17) 0.6554(16) 0.072(5) Uiso 1 1 d . . .
H24 H 0.633(2) 0.869(2) 0.2491(17) 0.093(6) Uiso 1 1 d . . .
H25 H 0.809(2) 0.9758(17) 0.1984(15) 0.073(5) Uiso 1 1 d . . .
H27 H 0.815(2) 0.953(2) 0.5162(17) 0.094(6) Uiso 1 1 d . . .
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
C1 N1 C2 111.83(12) . . ?
C1 N2 C3 112.02(13) . . ?
C2 N3 C3 113.98(13) . . ?
C3 N4 C4 122.56(12) . . ?
C3 N4 C10 120.95(12) . . ?
C4 N4 C10 116.35(10) . . ?
C19 N5 C21 117.62(14) . . ?
C27 N6 C23 117.11(15) . . ?
C2 O1 C16 117.93(12) . . ?
N1 C1 N2 129.65(14) . . ?
N1 C1 Cl1 115.34(11) . . ?
N2 C1 Cl1 115.01(13) . . ?
N3 C2 O1 119.79(14) . . ?
N3 C2 N1 126.90(15) . . ?
O1 C2 N1 113.31(12) . . ?
N3 C3 N2 125.61(12) . . ?
N3 C3 N4 116.99(13) . . ?
N2 C3 N4 117.39(13) . . ?
C5 C4 C9 119.66(15) . . ?
C5 C4 N4 121.21(14) . . ?
C9 C4 N4 119.02(15) . . ?
C4 C5 C6 119.33(18) . . ?
C4 C5 H5 119.1(11) . . ?
C6 C5 H5 121.6(11) . . ?
C7 C6 C5 120.69(19) . . ?
C7 C6 H6 119.2(14) . . ?
C5 C6 H6 120.0(14) . . ?
C8 C7 C6 119.96(18) . . ?
C8 C7 H7 120.5(12) . . ?
C6 C7 H7 119.5(12) . . ?
C7 C8 C9 119.91(19) . . ?
C7 C8 H8 121.8(14) . . ?
C9 C8 H8 118.3(14) . . ?
C4 C9 C8 120.44(19) . . ?
C4 C9 H9 119.0(11) . . ?
C8 C9 H9 120.5(11) . . ?
C15 C10 C11 120.55(15) . . ?
C15 C10 N4 119.55(15) . . ?
C11 C10 N4 119.79(14) . . ?
C10 C11 C12 119.73(19) . . ?
C10 C11 H11 120.5(12) . . ?
C12 C11 H11 119.7(12) . . ?
C13 C12 C11 119.9(2) . . ?
C13 C12 H12 124.8(12) . . ?
C11 C12 H12 115.3(12) . . ?
C14 C13 C12 120.50(18) . . ?
C14 C13 H13 119.3(12) . . ?
C12 C13 H13 120.2(12) . . ?
C13 C14 C15 120.04(19) . . ?
C13 C14 H14 123.7(14) . . ?
C15 C14 H14 116.3(14) . . ?
C10 C15 C14 119.27(19) . . ?
C10 C15 H15 119.5(11) . . ?
C14 C15 H15 121.2(11) . . ?
O1 C16 C17 110.60(14) . . ?
O1 C16 H16A 106.0(10) . . ?
C17 C16 H16A 108.9(10) . . ?
O1 C16 H16B 107.5(10) . . ?
C17 C16 H16B 112.0(10) . . ?
H16A C16 H16B 111.7(14) . . ?
C16 C17 C18 110.98(14) . . ?
C16 C17 H17A 109.6(10) . . ?
C18 C17 H17A 109.4(9) . . ?
C16 C17 H17B 112.3(11) . . ?
C18 C17 H17B 110.3(10) . . ?
H17A C17 H17B 104.0(14) . . ?
C19 C18 C22 116.04(16) . . ?
C19 C18 C17 122.75(14) . . ?
C22 C18 C17 121.19(15) . . ?
N5 C19 C18 124.85(15) . . ?
N5 C19 H19 119.0(11) . . ?
C18 C19 H19 116.0(11) . . ?
C22 C20 C21 119.66(15) . . ?
C22 C20 H20 120.3(13) . . ?
C21 C20 H20 120.0(13) . . ?
N5 C21 C20 121.55(15) . . ?
N5 C21 C23 116.81(13) . . ?
C20 C21 C23 121.62(13) . . ?
C20 C22 C18 120.13(16) . . ?
C20 C22 H22 120.4(11) . . ?
C18 C22 H22 119.5(11) . . ?
N6 C23 C24 121.51(15) . . ?
N6 C23 C21 116.73(14) . . ?
C24 C23 C21 121.74(13) . . ?
C25 C24 C23 119.52(16) . . ?
C25 C24 H24 121.3(13) . . ?
C23 C24 H24 119.1(13) . . ?
C24 C25 C26 120.32(17) . . ?
C24 C25 H25 118.4(11) . . ?
C26 C25 H25 121.1(11) . . ?
C25 C26 C27 115.93(17) . . ?
C25 C26 C28 122.86(18) . . ?
C27 C26 C28 121.21(17) . . ?
N6 C27 C26 125.61(17) . . ?
N6 C27 H27 117.1(12) . . ?
C26 C27 H27 117.3(12) . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
N1 C1 1.311(2) . ?
N1 C2 1.3408(19) . ?
N2 C1 1.3231(19) . ?
N2 C3 1.3491(19) . ?
N3 C2 1.3233(18) . ?
N3 C3 1.337(2) . ?
N4 C3 1.3588(18) . ?
N4 C4 1.4382(19) . ?
N4 C10 1.4428(18) . ?
N5 C19 1.334(2) . ?
N5 C21 1.3419(19) . ?
N6 C27 1.334(2) . ?
N6 C23 1.342(2) . ?
O1 C2 1.3254(19) . ?
O1 C16 1.462(2) . ?
Cl1 C1 1.7267(16) . ?
C4 C5 1.376(2) . ?
C4 C9 1.379(2) . ?
C5 C6 1.387(3) . ?
C5 H5 0.939(18) . ?
C6 C7 1.369(3) . ?
C6 H6 0.87(2) . ?
C7 C8 1.366(3) . ?
C7 H7 0.96(2) . ?
C8 C9 1.380(2) . ?
C8 H8 0.91(2) . ?
C9 H9 0.888(19) . ?
C10 C15 1.370(2) . ?
C10 C11 1.373(2) . ?
C11 C12 1.380(2) . ?
C11 H11 0.92(2) . ?
C12 C13 1.370(3) . ?
C12 H12 0.98(2) . ?
C13 C14 1.361(3) . ?
C13 H13 0.96(2) . ?
C14 C15 1.392(3) . ?
C14 H14 0.98(2) . ?
C15 H15 1.00(2) . ?
C16 C17 1.505(3) . ?
C16 H16A 0.986(18) . ?
C16 H16B 1.031(18) . ?
C17 C18 1.512(2) . ?
C17 H17A 1.023(18) . ?
C17 H17B 1.006(19) . ?
C18 C19 1.382(2) . ?
C18 C22 1.387(2) . ?
C19 H19 0.98(2) . ?
C20 C22 1.369(2) . ?
C20 C21 1.378(2) . ?
C20 H20 0.95(2) . ?
C21 C23 1.482(2) . ?
C22 H22 0.938(18) . ?
C23 C24 1.381(2) . ?
C24 C25 1.374(2) . ?
C24 H24 0.91(2) . ?
C25 C26 1.375(3) . ?
C25 H25 0.942(18) . ?
C26 C27 1.378(3) . ?
C26 C28 1.507(3) . ?
C27 H27 0.96(2) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25945467
