#------------------------------------------------------------------------------
#$Date: 2016-03-26 19:45:27 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180447 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/16/7211635.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_7211635
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 Cu2 N2 O10'
_chemical_formula_weight         521.37
_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                102.71(3)
_cell_angle_beta                 105.21(2)
_cell_angle_gamma                106.870(16)
_cell_formula_units_Z            2
_cell_length_a                   7.6284(11)
_cell_length_b                   11.058(2)
_cell_length_c                   11.284(5)
_cell_measurement_temperature    123(2)
_cell_volume                     832.6(5)
_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      123(2)
_diffrn_measured_fraction_theta_full 0.939
_diffrn_measured_fraction_theta_max 0.939
_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  0.0457
_diffrn_reflns_av_sigmaI/netI    0.1143
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5997
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    2.622
_exptl_absorpt_correction_T_max  0.8377
_exptl_absorpt_correction_T_min  0.6496
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            pale-green
_exptl_crystal_density_diffrn    2.080
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       sheet-like
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.492
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3076
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0563
_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)+(0.0919P)²+0.6856P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1593
_refine_ls_wR_factor_ref         0.1810
_reflns_number_gt                1848
_reflns_number_total             3076
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b911463g.txt
_cod_data_source_block           2a
_cod_original_cell_volume        832.6(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7211635
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 0.04544(14) 0.65614(9) 0.73873(9) 0.0219(3) Uani 1 1 d .
Cu2 Cu 0.52307(14) 1.43359(9) 1.26605(9) 0.0218(3) Uani 1 1 d .
O1W O -0.1022(8) 0.4681(5) 0.6512(5) 0.0277(13) Uani 1 1 d .
H1WA H -0.1620 0.4436 0.5699 0.033 Uiso 1 1 d R
H1WB H -0.1806 0.4383 0.6885 0.033 Uiso 1 1 d R
O2W O 0.3294(8) 1.3367(5) 1.3295(5) 0.0243(13) Uani 1 1 d .
H2WA H 0.3586 1.3557 1.4112 0.029 Uiso 1 1 d R
H2WB H 0.2979 1.2531 1.2975 0.029 Uiso 1 1 d R
O1 O 0.1746(8) 0.6623(5) 0.6116(5) 0.0295(14) Uani 1 1 d .
O2 O 0.3540(9) 0.8083(6) 0.5387(6) 0.0386(16) Uani 1 1 d .
O3 O 0.4521(8) 1.2810(5) 1.1155(5) 0.0209(12) Uani 1 1 d .
O4 O 0.2480(9) 1.1114(5) 1.1521(6) 0.0304(14) Uani 1 1 d .
O5 O 0.8658(9) 1.7909(5) 1.5089(6) 0.0348(15) Uani 1 1 d .
O6 O 0.6356(8) 1.5886(5) 1.4187(5) 0.0237(13) Uani 1 1 d .
O7 O 0.7279(8) 1.4701(5) 0.8342(5) 0.0244(13) Uani 1 1 d .
O8 O 0.9992(8) 1.6547(5) 0.8993(5) 0.0197(12) Uani 1 1 d .
N1 N 0.1928(9) 0.8506(6) 0.8064(6) 0.0194(15) Uani 1 1 d .
N2 N 0.7041(9) 1.5507(6) 1.2029(6) 0.0211(15) Uani 1 1 d .
C1 C 0.2925(11) 0.8959(7) 0.7326(7) 0.0183(17) Uani 1 1 d .
C2 C 0.4088(11) 1.0299(8) 0.7621(8) 0.0262(19) Uani 1 1 d .
C3 C 0.4186(11) 1.1151(8) 0.8802(7) 0.0202(17) Uani 1 1 d .
H3 H 0.4947 1.2076 0.9065 0.024 Uiso 1 1 calc R
C4 C 0.3216(12) 1.0683(8) 0.9578(7) 0.0237(18) Uani 1 1 d .
C5 C 0.2072(12) 0.9352(8) 0.9168(7) 0.0225(18) Uani 1 1 d .
H5 H 0.1364 0.9021 0.9681 0.027 Uiso 1 1 calc R
C6 C 0.2760(12) 0.7846(8) 0.6168(8) 0.0241(18) Uani 1 1 d .
C7 C 0.5079(12) 1.0862(8) 0.6778(7) 0.026(2) Uani 1 1 d .
H7A H 0.5911 1.0378 0.6577 0.040 Uiso 1 1 calc R
H7B H 0.5885 1.1808 0.7233 0.040 Uiso 1 1 calc R
H7C H 0.4093 1.0771 0.5972 0.040 Uiso 1 1 calc R
C8 C 0.3373(11) 1.1603(7) 1.0839(7) 0.0170(17) Uani 1 1 d .
C9 C 0.8058(10) 1.6740(7) 1.2901(7) 0.0167(16) Uani 1 1 d .
C10 C 0.9306(11) 1.7752(7) 1.2618(7) 0.0185(17) Uani 1 1 d .
C11 C 0.9497(11) 1.7399(8) 1.1395(8) 0.0250(19) Uani 1 1 d .
H11 H 1.0334 1.8055 1.1165 0.030 Uiso 1 1 calc R
C12 C 0.8491(11) 1.6113(8) 1.0511(7) 0.0185(17) Uani 1 1 d .
C13 C 0.7233(11) 1.5182(8) 1.0874(7) 0.0197(17) Uani 1 1 d .
H13 H 0.6503 1.4304 1.0285 0.024 Uiso 1 1 calc R
C14 C 0.7722(12) 1.6912(7) 1.4183(8) 0.0226(18) Uani 1 1 d .
C15 C 1.0325(11) 1.9184(7) 1.3487(7) 0.0228(18) Uani 1 1 d .
H15A H 0.9386 1.9496 1.3781 0.034 Uiso 1 1 calc R
H15B H 1.0866 1.9739 1.3004 0.034 Uiso 1 1 calc R
H15C H 1.1386 1.9248 1.4239 0.034 Uiso 1 1 calc R
C16 C 0.8582(11) 1.5753(7) 0.9171(8) 0.0191(17) 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
O1W Cu1 O8 94.7(2) . 1_445
O1W Cu1 O1 90.4(2) . .
O8 Cu1 O1 161.4(2) 1_445 .
O1W Cu1 N1 172.8(3) . .
O8 Cu1 N1 92.1(2) 1_445 .
O1 Cu1 N1 83.8(3) . .
O1W Cu1 O2W 81.3(2) . 2_577
O8 Cu1 O2W 80.8(2) 1_445 2_577
O1 Cu1 O2W 117.6(2) . 2_577
N1 Cu1 O2W 97.6(2) . 2_577
O6 Cu2 O3 171.0(2) . .
O6 Cu2 O2W 93.4(2) . .
O3 Cu2 O2W 92.9(2) . .
O6 Cu2 N2 82.8(3) . .
O3 Cu2 N2 91.6(2) . .
O2W Cu2 N2 172.3(2) . .
O6 Cu2 O7 89.3(2) . 2_687
O3 Cu2 O7 97.40(19) . 2_687
O2W Cu2 O7 87.4(2) . 2_687
N2 Cu2 O7 85.8(2) . 2_687
Cu1 O1W H1WA 117.3 . .
Cu1 O1W H1WB 110.1 . .
H1WA O1W H1WB 110.2 . .
Cu2 O2W H2WA 117.4 . .
Cu2 O2W H2WB 110.5 . .
H2WA O2W H2WB 108.0 . .
C6 O1 Cu1 114.5(5) . .
C8 O3 Cu2 131.1(5) . .
C14 O6 Cu2 116.8(5) . .
C16 O8 Cu1 128.9(5) . 1_665
C5 N1 C1 119.8(7) . .
C5 N1 Cu1 126.6(6) . .
C1 N1 Cu1 113.5(5) . .
C13 N2 C9 121.5(7) . .
C13 N2 Cu2 126.2(5) . .
C9 N2 Cu2 112.3(5) . .
N1 C1 C2 123.7(7) . .
N1 C1 C6 113.3(6) . .
C2 C1 C6 122.9(7) . .
C1 C2 C3 114.0(8) . .
C1 C2 C7 125.5(8) . .
C3 C2 C7 120.4(7) . .
C4 C3 C2 122.3(7) . .
C4 C3 H3 118.8 . .
C2 C3 H3 118.8 . .
C5 C4 C3 118.3(8) . .
C5 C4 C8 120.3(8) . .
C3 C4 C8 121.4(7) . .
N1 C5 C4 121.7(8) . .
N1 C5 H5 119.1 . .
C4 C5 H5 119.1 . .
O2 C6 O1 123.7(7) . .
O2 C6 C1 121.9(7) . .
O1 C6 C1 114.4(7) . .
C2 C7 H7A 109.5 . .
C2 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C2 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
O4 C8 O3 125.7(7) . .
O4 C8 C4 118.6(7) . .
O3 C8 C4 115.6(7) . .
N2 C9 C10 121.7(7) . .
N2 C9 C14 114.2(7) . .
C10 C9 C14 124.1(7) . .
C9 C10 C11 116.3(7) . .
C9 C10 C15 124.6(7) . .
C11 C10 C15 119.0(7) . .
C12 C11 C10 121.8(8) . .
C12 C11 H11 119.1 . .
C10 C11 H11 119.1 . .
C11 C12 C13 117.4(7) . .
C11 C12 C16 122.1(7) . .
C13 C12 C16 120.3(7) . .
N2 C13 C12 121.2(7) . .
N2 C13 H13 119.4 . .
C12 C13 H13 119.4 . .
O5 C14 O6 124.8(8) . .
O5 C14 C9 121.6(8) . .
O6 C14 C9 113.6(6) . .
C10 C15 H15A 109.5 . .
C10 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C10 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
O7 C16 O8 126.3(7) . .
O7 C16 C12 117.5(7) . .
O8 C16 C12 116.2(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1W 1.929(5) .
Cu1 O8 1.937(5) 1_445
Cu1 O1 1.944(6) .
Cu1 N1 1.973(6) .
Cu1 O2W 2.789(5) 2_577
Cu2 O6 1.927(5) .
Cu2 O3 1.937(5) .
Cu2 O2W 1.954(6) .
Cu2 N2 1.994(7) .
Cu2 O7 2.580(5) 2_687
O1W H1WA 0.8500 .
O1W H1WB 0.8499 .
O2W H2WA 0.8500 .
O2W H2WB 0.8500 .
O1 C6 1.329(10) .
O2 C6 1.219(10) .
O3 C8 1.275(9) .
O4 C8 1.262(10) .
O5 C14 1.198(9) .
O6 C14 1.301(10) .
O7 C16 1.256(9) .
O8 C16 1.269(9) .
O8 Cu1 1.937(5) 1_665
N1 C5 1.340(10) .
N1 C1 1.348(10) .
N2 C13 1.332(10) .
N2 C9 1.350(10) .
C1 C2 1.400(11) .
C1 C6 1.534(11) .
C2 C3 1.423(11) .
C2 C7 1.493(11) .
C3 C4 1.378(12) .
C3 H3 0.9500 .
C4 C5 1.374(11) .
C4 C8 1.509(11) .
C5 H5 0.9500 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C9 C10 1.400(11) .
C9 C14 1.516(11) .
C10 C11 1.406(11) .
C10 C15 1.509(10) .
C11 C12 1.396(11) .
C11 H11 0.9500 .
C12 C13 1.402(11) .
C12 C16 1.502(10) .
C13 H13 0.9500 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
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 O1 0.85 2.09 2.824(8) 144.9 2_566
O1W H1WB O7 0.85 1.95 2.710(8) 148.3 1_445
O2W H2WA O6 0.85 1.87 2.695(7) 164.5 2_688
O2W H2WB O4 0.85 1.87 2.618(8) 146.5 .
