#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:45:27 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180447 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/16/7211636.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_7211636
loop_
_publ_author_name
'Li, Cui-Jin'
'Lin, Zhuojia'
'Yun, Lei'
'Xie, Yu-Ling'
'Leng, Ji-Dong'
'Ou, Yong-Cong'
'Tong, Ming-Liang'
_publ_section_title
;
 Hydrothermal in situ ligand reaction: copper(II)-mediated stepwise
 oxidation of 2,3,5- and 2,4,6-trimethylpyridine to pyridinecarboxylates
;
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              425
_journal_paper_doi               10.1039/b911463g
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C16 H14 Cu4 N2 O22'
_chemical_formula_weight         840.45
_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                101.345(2)
_cell_angle_beta                 107.878(2)
_cell_angle_gamma                111.340(2)
_cell_formula_units_Z            1
_cell_length_a                   7.0602(7)
_cell_length_b                   9.5054(10)
_cell_length_c                   10.8957(11)
_cell_measurement_temperature    293(2)
_cell_volume                     607.69(11)
_computing_cell_refinement       'Bruker SMART (Bruker, 1998)'
_computing_data_collection       'Bruker SMART (Bruker, 1998)'
_computing_data_reduction        'Bruker SAINT + & SHELXTL (Bruker, 1998)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'φ and ω 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  0.0143
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3295
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    3.565
_exptl_absorpt_correction_T_max  0.7169
_exptl_absorpt_correction_T_min  0.4575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    2.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2332
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0304
_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)+(0.0454P)²+0.5933P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0843
_reflns_number_gt                2179
_reflns_number_total             2332
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b911463g.txt
_cod_data_source_block           4
_cod_original_sg_symbol_H-M      p-1
_cod_database_code               7211636
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
Cu1 Cu 0.68780(5) 1.40354(4) 0.09786(3) 0.01899(13) Uani 1 1 d .
Cu2 Cu -0.24071(5) 0.90212(4) -0.52403(3) 0.02244(13) Uani 1 1 d .
N1 N 0.3806(4) 1.2751(3) -0.0224(2) 0.0187(5) Uani 1 1 d .
O1 O 0.7101(3) 1.3603(2) -0.0881(2) 0.0223(4) Uani 1 1 d .
O2 O 0.5106(3) 1.2217(3) -0.30904(19) 0.0234(5) Uani 1 1 d .
O3 O -0.3901(3) 0.9021(3) -0.4056(2) 0.0262(5) Uani 1 1 d .
O4 O -0.4277(3) 0.9496(3) -0.2109(2) 0.0294(5) Uani 1 1 d .
O5 O 0.2275(4) 1.3303(3) 0.2512(2) 0.0273(5) Uani 1 1 d .
O6 O 0.5514(3) 1.4366(3) 0.2325(2) 0.0236(4) Uani 1 1 d .
O7 O 0.0509(3) 1.0408(3) -0.3779(2) 0.0283(5) Uani 1 1 d .
O1W O 0.7652(4) 1.2174(3) 0.1514(3) 0.0327(5) Uani 1 1 d .
H1WA H 0.6754 1.1639 0.1810 0.055(14) Uiso 1 1 d R
H1WB H 0.8978 1.2398 0.2021 0.042(12) Uiso 1 1 d R
O2W O 0.9801(3) 1.5745(3) 0.2005(2) 0.0284(5) Uani 1 1 d .
H2WA H 1.0489 1.6085 0.2876 0.034 Uiso 1 1 d R
H2WB H 1.0757 1.5883 0.1662 0.034 Uiso 1 1 d R
O3W O -0.2198(4) 0.6684(3) -0.5044(2) 0.0302(5) Uani 1 1 d .
H3WA H -0.3048 0.5871 -0.5773 0.049(12) Uiso 1 1 d R
H3WB H -0.2508 0.6504 -0.4381 0.052(13) Uiso 1 1 d R
O4W O 1.1657(8) 1.6514(7) 0.4666(5) 0.0354(11) Uani 0.50 1 d P
O4W' O 1.1603(9) 1.7568(10) 0.4572(6) 0.0548(17) Uani 0.50 1 d P
C1 C 0.3242(5) 1.2086(3) -0.1562(3) 0.0175(6) Uani 1 1 d .
C2 C 0.1010(5) 1.1044(3) -0.2465(3) 0.0186(6) Uani 1 1 d .
C3 C -0.0610(4) 1.0741(3) -0.1913(3) 0.0175(6) Uani 1 1 d .
C4 C 0.0080(4) 1.1485(3) -0.0513(3) 0.0175(5) Uani 1 1 d .
H4 H -0.0964 1.1303 -0.0135 0.021 Uiso 1 1 calc R
C5 C 0.2318(5) 1.2498(3) 0.0317(3) 0.0174(5) Uani 1 1 d .
C6 C 0.5254(5) 1.2645(3) -0.1890(3) 0.0190(6) Uani 1 1 d .
C7 C -0.3104(5) 0.9673(3) -0.2746(3) 0.0196(6) Uani 1 1 d .
C8 C 0.3401(5) 1.3454(3) 0.1847(3) 0.0195(6) Uani 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'
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_1
_geom_angle_site_symmetry_3
O2W Cu1 N1 164.54(10) . .
O2W Cu1 O6 99.63(9) . .
N1 Cu1 O6 80.61(9) . .
O2W Cu1 O1 96.30(9) . .
N1 Cu1 O1 79.92(9) . .
O6 Cu1 O1 157.78(9) . .
O2W Cu1 O1W 96.23(10) . .
N1 Cu1 O1W 99.10(10) . .
O6 Cu1 O1W 96.67(9) . .
O1 Cu1 O1W 96.89(9) . .
O3 Cu2 O7 93.84(9) . .
O3 Cu2 O2 95.06(9) . 2_574
O7 Cu2 O2 170.01(9) . 2_574
O3 Cu2 O7 165.90(9) . 2_574
O7 Cu2 O7 76.92(9) . 2_574
O2 Cu2 O7 93.48(8) 2_574 2_574
O3 Cu2 O3W 92.03(9) . .
O7 Cu2 O3W 93.29(9) . .
O2 Cu2 O3W 90.90(9) 2_574 .
O7 Cu2 O3W 99.03(9) 2_574 .
O3 Cu2 Cu2 131.79(6) . 2_574
O7 Cu2 Cu2 38.80(6) . 2_574
O2 Cu2 Cu2 131.54(6) 2_574 2_574
O7 Cu2 Cu2 38.12(6) 2_574 2_574
O3W Cu2 Cu2 97.89(6) . 2_574
C5 N1 C1 122.8(2) . .
C5 N1 Cu1 118.25(19) . .
C1 N1 Cu1 118.88(19) . .
C6 O1 Cu1 113.69(18) . .
C6 O2 Cu2 127.18(18) . 2_574
C7 O3 Cu2 130.07(19) . .
C8 O6 Cu1 114.29(18) . .
C2 O7 Cu2 127.59(18) . .
C2 O7 Cu2 128.25(18) . 2_574
Cu2 O7 Cu2 103.08(9) . 2_574
Cu1 O1W H1WA 111.2 . .
Cu1 O1W H1WB 120.3 . .
H1WA O1W H1WB 110.0 . .
Cu1 O2W H2WA 124.8 . .
Cu1 O2W H2WB 119.3 . .
H2WA O2W H2WB 108.4 . .
Cu2 O3W H3WA 113.3 . .
Cu2 O3W H3WB 109.0 . .
H3WA O3W H3WB 110.1 . .
N1 C1 C2 120.5(3) . .
N1 C1 C6 111.1(2) . .
C2 C1 C6 128.4(3) . .
O7 C2 C1 119.0(2) . .
O7 C2 C3 123.1(3) . .
C1 C2 C3 117.9(2) . .
C4 C3 C2 118.8(2) . .
C4 C3 C7 116.3(2) . .
C2 C3 C7 124.8(2) . .
C5 C4 C3 120.1(2) . .
C5 C4 H4 120.0 . .
C3 C4 H4 120.0 . .
N1 C5 C4 119.9(2) . .
N1 C5 C8 111.8(2) . .
C4 C5 C8 128.3(3) . .
O2 C6 O1 121.9(3) . .
O2 C6 C1 122.1(2) . .
O1 C6 C1 116.0(2) . .
O4 C7 O3 122.7(3) . .
O4 C7 C3 116.8(2) . .
O3 C7 C3 120.4(2) . .
O5 C8 O6 125.8(3) . .
O5 C8 C5 120.0(3) . .
O6 C8 C5 114.1(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O2W 1.892(2) .
Cu1 N1 1.900(2) .
Cu1 O6 2.021(2) .
Cu1 O1 2.053(2) .
Cu1 O1W 2.164(2) .
Cu2 O3 1.900(2) .
Cu2 O7 1.923(2) .
Cu2 O2 1.9294(19) 2_574
Cu2 O7 1.952(2) 2_574
Cu2 O3W 2.325(2) .
Cu2 Cu2 3.0348(7) 2_574
N1 C5 1.327(4) .
N1 C1 1.335(4) .
O1 C6 1.264(3) .
O2 C6 1.251(3) .
O2 Cu2 1.9294(19) 2_574
O3 C7 1.282(3) .
O4 C7 1.222(3) .
O5 C8 1.220(4) .
O6 C8 1.285(4) .
O7 C2 1.316(3) .
O7 Cu2 1.952(2) 2_574
O1W H1WA 0.8485 .
O1W H1WB 0.8469 .
O2W H2WA 0.8500 .
O2W H2WB 0.8500 .
O3W H3WA 0.8467 .
O3W H3WB 0.8476 .
O4W O4W' 1.040(8) .
C1 C2 1.400(4) .
C1 C6 1.504(4) .
C2 C3 1.416(4) .
C3 C4 1.390(4) .
C3 C7 1.519(4) .
C4 C5 1.383(4) .
C4 H4 0.9300 .
C5 C8 1.519(4) .
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
O1W H1WA O4 0.85 1.86 2.687(3) 166.0 2_575
O1W H1WB O5 0.85 2.01 2.792(3) 153.2 1_655
O2W H2WB O1 0.85 1.91 2.762(3) 174.0 2_785
O3W H3WA O6 0.85 1.96 2.787(3) 163.6 1_444
O3W H3WB O5 0.85 1.96 2.773(3) 161.3 2_575
