# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2009
data_global
_journal_name_full 'Dalton Trans.'
_journal_coden_Cambridge 0222
_publ_contact_author_name 'Evgenia Spodine'
_publ_contact_author_email ESPODINE@UCHILE.CL
_publ_section_title
;
[Cu(H2btec)(bipy)]\/Y: Novel Metal Organic Framework
(MOF) as Heterogeneous Catalyst for the Oxidation of Olefins
;
loop_
_publ_author_name
'Evgenia Spodine'
'Pedro A Aguirre'
'Ricardo F Baggio'
'Kareen Brown'
'Miguel A Novak'
;
V.Paredes-Garcia
;
'Diego Venegas-Yazigi'
'Santiago Zolezzi'
# Attachment 'Cu_H2btec__bipy_-CIF.cif'
data_tmp
_database_code_depnum_ccdc_archive 'CCDC 682181'
_audit_update_record
;
2007-04-20 # Formatted by publCIF
;
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
Catena-Poly [(2,2'-bipyridine-\k^2^N,N')
copper(II)-\m~2~-1,4'-benzene-tetracarboxylate-k^2^ O^1^:O^2^)]
;
_chemical_name_common
;
Catena-Poly ((2,2'-bipyridine-kappa$2!N,N') copper(ii)-mu!2$-
1,4'-benzene-tetracarboxylate-k$2! O$1!:O$2!))
;
_chemical_melting_point ?
_chemical_formula_moiety 'C20 H12 Cu N2 O8'
_chemical_formula_sum 'C20 H12 Cu N2 O8'
_chemical_formula_weight 471.86
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M ' C 2/c '
_symmetry_space_group_name_Hall '-C 2yc '
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'
_cell_length_a 10.1810(18)
_cell_length_b 14.4360(18)
_cell_length_c 12.894(3)
_cell_angle_alpha 90.00
_cell_angle_beta 112.94(3)
_cell_angle_gamma 90.00
_cell_volume 1745.2(7)
_cell_formula_units_Z 4
_cell_measurement_temperature 294(2)
_cell_measurement_reflns_used 1828
_cell_measurement_theta_min 2.577
_cell_measurement_theta_max 22.079
_exptl_crystal_description Plate
_exptl_crystal_colour Blue
_exptl_crystal_size_max 0.60
_exptl_crystal_size_mid 0.25
_exptl_crystal_size_min 0.10
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.796
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 956
_exptl_absorpt_coefficient_mu 1.310
_exptl_absorpt_correction_T_min 0.68
_exptl_absorpt_correction_T_max 0.88
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'SADABS (Sheldrick, 2001)'
_diffrn_ambient_temperature 294(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 7220
_diffrn_reflns_av_R_equivalents 0.0360
_diffrn_reflns_av_sigmaI/netI 0.0360
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -18
_diffrn_reflns_limit_k_max 18
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_theta_min 2.59
_diffrn_reflns_theta_max 27.89
_reflns_number_total 1972
_reflns_number_gt 1664
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'SMART-NT (Bruker, 2001)'
_computing_cell_refinement 'SAINT-NT (Bruker, 2001 )'
_computing_data_reduction 'SAINT-NT (Bruker, 2001 )'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'SHELXTL-NT (Bruker, 2001)'
_computing_publication_material
'SHELXTL-NT (Bruker, 2001), PLATON (Spek, 2003)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0774P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 1972
_refine_ls_number_parameters 146
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0515
_refine_ls_R_factor_gt 0.0420
_refine_ls_wR_factor_ref 0.1179
_refine_ls_wR_factor_gt 0.1121
_refine_ls_goodness_of_fit_ref 1.054
_refine_ls_restrained_S_all 1.054
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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 0.5000 0.19461(3) 0.2500 0.02938(18) Uani 1 2 d S . .
O1 O 0.5477(2) 0.28961(13) 0.36461(17) 0.0411(5) Uani 1 1 d . . .
O2 O 0.3237(3) 0.29128(15) 0.3498(2) 0.0591(7) Uani 1 1 d . . .
O3 O 0.5547(3) 0.25988(13) 0.60272(17) 0.0554(6) Uani 1 1 d . . .
O4 O 0.6949(2) 0.35270(15) 0.73635(17) 0.0521(6) Uani 1 1 d . . .
H4A H 0.729(4) 0.303(2) 0.764(4) 0.057(11) Uiso 1 1 d . . .
N1 N 0.5669(2) 0.09132(15) 0.35828(18) 0.0320(5) Uani 1 1 d . . .
C1 C 0.6412(3) 0.0989(2) 0.4691(2) 0.0420(7) Uani 1 1 d . . .
H1 H 0.6605 0.1575 0.5015 0.050 Uiso 1 1 calc R . .
C2 C 0.6899(3) 0.0224(3) 0.5365(3) 0.0551(9) Uani 1 1 d . . .
H2 H 0.7409 0.0290 0.6136 0.066 Uiso 1 1 calc R . .
C3 C 0.6626(4) -0.0639(3) 0.4888(3) 0.0584(9) Uani 1 1 d . . .
H3 H 0.6944 -0.1165 0.5332 0.070 Uiso 1 1 calc R . .
C4 C 0.5881(3) -0.0720(2) 0.3752(3) 0.0484(8) Uani 1 1 d . . .
H4 H 0.5698 -0.1302 0.3416 0.058 Uiso 1 1 calc R . .
C5 C 0.5404(3) 0.00670(17) 0.3111(2) 0.0333(6) Uani 1 1 d . . .
C6 C 0.4747(3) 0.41273(16) 0.4485(2) 0.0281(5) Uani 1 1 d . . .
C7 C 0.5476(3) 0.42041(16) 0.5648(2) 0.0285(5) Uani 1 1 d . . .
C8 C 0.5713(3) 0.50781(17) 0.6141(2) 0.0309(5) Uani 1 1 d . . .
H8 H 0.6196 0.5127 0.6917 0.037 Uiso 1 1 calc R . .
C9 C 0.4452(3) 0.32233(17) 0.3842(2) 0.0341(6) Uani 1 1 d . . .
C10 C 0.5975(3) 0.33555(19) 0.6354(2) 0.0337(6) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0404(3) 0.0205(3) 0.0256(3) 0.000 0.0110(2) 0.000
O1 0.0568(13) 0.0276(10) 0.0378(11) -0.0082(8) 0.0171(10) 0.0001(8)
O2 0.0500(14) 0.0441(13) 0.0716(17) -0.0319(11) 0.0109(12) -0.0137(10)
O3 0.0927(17) 0.0223(10) 0.0383(12) 0.0006(8) 0.0114(11) -0.0062(10)
O4 0.0675(14) 0.0302(11) 0.0337(11) 0.0091(8) -0.0074(10) -0.0004(10)
N1 0.0363(11) 0.0275(11) 0.0304(11) 0.0016(9) 0.0110(9) 0.0036(9)
C1 0.0417(15) 0.0501(17) 0.0290(14) 0.0009(12) 0.0083(12) 0.0048(13)
C2 0.0459(17) 0.082(3) 0.0362(16) 0.0208(16) 0.0151(14) 0.0125(17)
C3 0.059(2) 0.056(2) 0.065(2) 0.0338(18) 0.0287(18) 0.0177(16)
C4 0.0554(18) 0.0286(15) 0.068(2) 0.0148(14) 0.0315(17) 0.0063(13)
C5 0.0373(13) 0.0249(13) 0.0419(15) 0.0046(11) 0.0199(12) 0.0015(10)
C6 0.0326(12) 0.0226(12) 0.0239(12) -0.0040(9) 0.0054(10) -0.0022(9)
C7 0.0342(13) 0.0202(11) 0.0248(12) -0.0016(9) 0.0046(10) 0.0001(9)
C8 0.0372(13) 0.0271(13) 0.0203(11) -0.0034(9) 0.0024(10) -0.0020(10)
C9 0.0483(16) 0.0223(12) 0.0233(12) -0.0041(9) 0.0050(11) -0.0020(11)
C10 0.0443(15) 0.0258(12) 0.0288(13) 0.0022(10) 0.0118(11) 0.0014(11)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O1 1.9341(19) 2_655 ?
Cu1 O1 1.9342(19) . y
Cu1 N1 1.973(2) . y
Cu1 N1 1.974(2) 2_655 ?
O1 C9 1.257(4) . ?
O2 C9 1.225(4) . ?
O3 C10 1.190(3) . ?
O4 C10 1.316(3) . ?
O4 H4A 0.82(3) . ?
N1 C1 1.336(3) . ?
N1 C5 1.344(3) . ?
C1 C2 1.373(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.368(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(4) . ?
C4 H4 0.9300 . ?
C5 C5 1.466(6) 2_655 ?
C6 C8 1.375(3) 5_666 ?
C6 C7 1.394(3) . ?
C6 C9 1.513(3) . ?
C7 C8 1.391(3) . ?
C7 C10 1.492(3) . ?
C8 C6 1.375(3) 5_666 ?
C8 H8 0.9300 . ?
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
O1 Cu1 O1 89.69(12) 2_655 . ?
O1 Cu1 N1 172.24(8) 2_655 . ?
O1 Cu1 N1 94.62(9) . . y
O1 Cu1 N1 94.62(9) 2_655 2_655 ?
O1 Cu1 N1 172.24(8) . 2_655 y
N1 Cu1 N1 81.86(13) . 2_655 y
C9 O1 Cu1 116.01(18) . . ?
C10 O4 H4A 107(3) . . ?
C1 N1 C5 119.3(2) . . ?
C1 N1 Cu1 126.2(2) . . ?
C5 N1 Cu1 114.41(17) . . ?
N1 C1 C2 121.7(3) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 119.4(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 121.1(3) . . ?
N1 C5 C5 114.58(14) . 2_655 ?
C4 C5 C5 124.34(18) . 2_655 ?
C8 C6 C7 118.8(2) 5_666 . ?
C8 C6 C9 116.6(2) 5_666 . ?
C7 C6 C9 124.6(2) . . ?
C8 C7 C6 119.3(2) . . ?
C8 C7 C10 120.6(2) . . ?
C6 C7 C10 120.2(2) . . ?
C6 C8 C7 122.0(2) 5_666 . ?
C6 C8 H8 119.0 5_666 . ?
C7 C8 H8 119.0 . . ?
O2 C9 O1 126.2(2) . . ?
O2 C9 C6 118.1(3) . . ?
O1 C9 C6 115.6(2) . . ?
O3 C10 O4 123.6(3) . . ?
O3 C10 C7 123.2(2) . . ?
O4 C10 C7 113.3(2) . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4A O2 0.82(3) 1.78(4) 2.585(3) 167(4) 8_556
C1 H1 O3 0.93 2.48 3.214(4) 136 .
C4 H4 O3 0.93 2.52 3.142(4) 125 5_656
loop_
_publ_manuscript_incl_extra_item
'_geom_extra_tableA_col_1'
'_geom_extra_tableA_col_2'
'_geom_extra_tableA_col_3'
'_geom_extra_tableA_col_4'
'_geom_extra_tableA_col_5'
'_geom_extra_table_head_A'
'_geom_table_footnote_A'
_geom_extra_table_head_A
;
\p-\p contacts (\%A, \%) for (1)
;
loop_
_geom_extra_tableA_col_1
_geom_extra_tableA_col_2
_geom_extra_tableA_col_3
_geom_extra_tableA_col_4
_geom_extra_tableA_col_5
Group1-Group2 ? ipd(\%A) ccd(\%A) sa(\%)
'Cg1 -> Cg1#1' ? 3.629(2) 22.3(1) 3.36(1)
'Cg1 -> Cg2#2' ? 3.656(2) 23.4(2) 3.37(2)
? ? ? ? ?
_geom_table_footnote_A
;
Group codes.- Cg1: N1,C1,C2,C3,C4,C5, Cg2: C6,C7,C8,C6,C7,C8
Symmetry codes.- #1 = 1-x,-y,1-z; #2 = 1/2+x,-1/2+y,z
ipd: interplanar distance (Distance from one plane to the
neighbouring centroid); ccd: center-to-center distance (Distance
between ring centroids); sa: slippage angle (Angle subtended by
the intercentroid vector to the plane normal).
For details, see Janiak 2000)
;
_diffrn_measured_fraction_theta_max 0.941
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max 0.541
_refine_diff_density_min -0.278
_refine_diff_density_rms 0.103
_publ_section_references
;
Allen, F. H. (2002). Acta Cryst. B58, 380--388.
Bruker (2001). SMART-NT (Version 5.624), SAINT-NT (Version 6.04)
and SHELXTL-NT (Version 6.10) for Windows NT. Bruker AXS Inc., Madison,
Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876--881.
Sheldrick, G. M. (2001). SADABS (Version 2.05). University of
G\"ottingen, Germany.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of
G\"ottingen, Germany.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7--?13.
;