#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/76/1517640.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_1517640
loop_
_publ_author_name
'Tiffany M. Smith'
'Jose Vargas'
'Diona Symester'
'Michael Tichenor'
'Charles J. O-Connor'
'Jon Zubieta'
_publ_section_title
;
 Metal-organophosphonate chemistry: Hydrothermal syntheses and structures
 of copper(II)-xylyldiphosphonates with organonitrogen coligands
;
_journal_name_full
;
Inorganica Chimica Acta
;
_journal_page_first              63
_journal_page_last               77
_journal_volume                  403
_journal_year                    2013
_chemical_formula_moiety         'C20 H18 Cu N2 O6 P2'
_chemical_formula_sum            'C20 H18 Cu N2 O6 P2'
_chemical_formula_weight         507.84
_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
_cell_angle_alpha                116.331(2)
_cell_angle_beta                 111.017(3)
_cell_angle_gamma                92.971(3)
_cell_formula_units_Z            2
_cell_length_a                   9.7161(16)
_cell_length_b                   11.3506(18)
_cell_length_c                   11.3710(18)
_cell_measurement_reflns_used    9896
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      34.40
_cell_measurement_theta_min      2.32
_cell_volume                     1015.3(3)
_computing_cell_refinement       'Bruker SAINT (Bruker, 2011)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2011)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2011)'
_computing_molecular_graphics    'CrystalMaker (Palmer, 2010)'
_computing_publication_material  'Bruker SHELXTL (Bruker, 2011)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0141
_diffrn_reflns_av_sigmaI/netI    0.0119
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_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            13422
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    1.276
_exptl_absorpt_correction_T_max  0.747
_exptl_absorpt_correction_T_min  0.639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS SHELXL-97 (Sheldrick, 2008)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             518
_exptl_crystal_size_max          0.335
_exptl_crystal_size_mid          0.312
_exptl_crystal_size_min          0.214
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0205
_refine_ls_R_factor_gt           0.0200
_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)+(0.0302P)²+1.0333P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0572
_refine_ls_wR_factor_ref         0.0576
_reflns_number_gt                3503
_reflns_number_total             3584
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ICA-2013-403-63-77-6.cif
_cod_data_source_block           compound_6
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1517640
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 0.62974(2) 0.874531(19) 0.88516(2) 0.00917(7) Uani 1 1 d .
P1 P 0.66742(5) 1.01908(4) 1.20998(4) 0.00938(10) Uani 1 1 d .
P2 P 0.74479(5) 1.20007(4) 0.99268(4) 0.01027(10) Uani 1 1 d .
O1 O 0.74848(13) 1.05874(11) 0.96972(12) 0.0125(2) Uani 1 1 d .
O2 O 0.60160(13) 0.90592(11) 1.05372(12) 0.0110(2) Uani 1 1 d .
O3 O 0.61947(13) 1.14989(11) 1.23313(12) 0.0116(2) Uani 1 1 d .
O4 O 0.62228(13) 0.96303(12) 1.29851(12) 0.0137(2) Uani 1 1 d .
H4' H 0.5386 0.9084 1.2468 0.021 Uiso 1 1 calc R
O5 O 0.63611(13) 1.20754(12) 0.86426(13) 0.0152(3) Uani 1 1 d .
O6 O 0.72145(14) 1.28784(12) 1.13424(13) 0.0151(3) Uani 1 1 d .
H6' H 0.6879 1.2374 1.1569 0.023 Uiso 1 1 calc R
N1 N 0.62713(15) 0.67929(14) 0.83640(15) 0.0118(3) Uani 1 1 d .
N2 N 0.66825(15) 0.81256(14) 0.70695(15) 0.0119(3) Uani 1 1 d .
C1 C 0.68082(19) 0.88168(18) 0.64123(18) 0.0148(3) Uani 1 1 d .
H1 H 0.6701 0.9702 0.6783 0.018 Uiso 1 1 calc R
C2 C 0.7098(2) 0.82520(19) 0.51745(19) 0.0181(4) Uani 1 1 d .
H2 H 0.7157 0.8752 0.4723 0.022 Uiso 1 1 calc R
C3 C 0.7293(2) 0.69576(19) 0.46357(19) 0.0186(4) Uani 1 1 d .
H3 H 0.7508 0.6584 0.3830 0.022 Uiso 1 1 calc R
C4 C 0.71658(19) 0.61941(18) 0.53079(18) 0.0159(4) Uani 1 1 d .
C5 C 0.7293(2) 0.48167(19) 0.48180(19) 0.0200(4) Uani 1 1 d .
H5 H 0.7525 0.4387 0.4027 0.024 Uiso 1 1 calc R
C6 C 0.7084(2) 0.41306(18) 0.5483(2) 0.0200(4) Uani 1 1 d .
H6 H 0.7166 0.3238 0.5136 0.024 Uiso 1 1 calc R
C7 C 0.67358(19) 0.47594(17) 0.67189(19) 0.0157(4) Uani 1 1 d .
C8 C 0.64836(19) 0.41183(18) 0.7467(2) 0.0177(4) Uani 1 1 d .
H8 H 0.6545 0.3224 0.7175 0.021 Uiso 1 1 calc R
C9 C 0.6147(2) 0.48219(18) 0.8629(2) 0.0178(4) Uani 1 1 d .
H9 H 0.5987 0.4408 0.9132 0.021 Uiso 1 1 calc R
C10 C 0.60454(19) 0.61681(17) 0.90527(19) 0.0149(3) Uani 1 1 d .
H10 H 0.5813 0.6635 0.9837 0.018 Uiso 1 1 calc R
C11 C 0.66141(18) 0.61050(17) 0.72215(18) 0.0122(3) Uani 1 1 d .
C12 C 0.68353(18) 0.68307(17) 0.65179(18) 0.0124(3) Uani 1 1 d .
C13 C 0.87365(18) 1.05750(17) 1.28703(18) 0.0125(3) Uani 1 1 d .
H13A H 0.9109 1.1140 1.2556 0.015 Uiso 1 1 calc R
H13B H 0.9141 1.1084 1.3920 0.015 Uiso 1 1 calc R
C14 C 0.93020(18) 0.92986(17) 1.24190(18) 0.0125(3) Uani 1 1 d .
C15 C 0.97192(18) 0.88326(17) 1.12654(18) 0.0127(3) Uani 1 1 d .
H15 H 0.9695 0.9339 1.0805 0.015 Uiso 1 1 calc R
C16 C 1.01711(18) 0.76217(17) 1.07907(18) 0.0129(3) Uani 1 1 d .
C17 C 1.02157(19) 0.68798(18) 1.14997(19) 0.0157(4) Uani 1 1 d .
H17 H 1.0519 0.6073 1.1199 0.019 Uiso 1 1 calc R
C18 C 0.9810(2) 0.73349(19) 1.2653(2) 0.0179(4) Uani 1 1 d .
H18 H 0.9847 0.6834 1.3121 0.021 Uiso 1 1 calc R
C19 C 0.93509(19) 0.85348(18) 1.31069(19) 0.0159(4) Uani 1 1 d .
H19 H 0.9074 0.8832 1.3875 0.019 Uiso 1 1 calc R
C20 C 0.93600(19) 1.28724(17) 1.04474(18) 0.0139(3) Uani 1 1 d .
H20A H 0.9427 1.3837 1.0835 0.017 Uiso 1 1 calc R
H20B H 1.0072 1.2751 1.1214 0.017 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'
P P 0.1023 0.0942 '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
O2 Cu1 O1 95.35(5) . .
O2 Cu1 N2 170.28(5) . .
O1 Cu1 N2 91.42(5) . .
O2 Cu1 N1 89.14(5) . .
O1 Cu1 N1 148.31(5) . .
N2 Cu1 N1 81.46(6) . .
O2 Cu1 O3 89.91(5) . 2_677
O1 Cu1 O3 111.94(5) . 2_677
N2 Cu1 O3 94.03(5) . 2_677
N1 Cu1 O3 99.39(5) . 2_677
O2 P1 O3 115.11(7) . .
O2 P1 O4 107.58(7) . .
O3 P1 O4 110.53(7) . .
O2 P1 C13 109.81(7) . .
O3 P1 C13 108.43(7) . .
O4 P1 C13 104.89(7) . .
O5 P2 O1 115.79(7) . .
O5 P2 O6 112.11(7) . .
O1 P2 O6 110.29(7) . .
O5 P2 C20 108.83(8) . .
O1 P2 C20 107.44(7) . .
O6 P2 C20 101.27(7) . .
P2 O1 Cu1 146.28(8) . .
P1 O2 Cu1 135.29(7) . .
P1 O3 Cu1 115.52(6) . 2_677
P1 O4 H4' 109.5 . .
P2 O6 H6' 109.5 . .
C10 N1 C11 118.70(15) . .
C10 N1 Cu1 128.46(12) . .
C11 N1 Cu1 112.73(11) . .
C1 N2 C12 118.61(15) . .
C1 N2 Cu1 128.36(12) . .
C12 N2 Cu1 113.02(11) . .
N2 C1 C2 122.05(16) . .
N2 C1 H1 119.0 . .
C2 C1 H1 119.0 . .
C3 C2 C1 119.57(16) . .
C3 C2 H2 120.2 . .
C1 C2 H2 120.2 . .
C2 C3 C4 119.82(16) . .
C2 C3 H3 120.1 . .
C4 C3 H3 120.1 . .
C12 C4 C3 116.57(16) . .
C12 C4 C5 118.32(16) . .
C3 C4 C5 125.07(16) . .
C6 C5 C4 121.48(16) . .
C6 C5 H5 119.3 . .
C4 C5 H5 119.3 . .
C5 C6 C7 121.16(17) . .
C5 C6 H6 119.4 . .
C7 C6 H6 119.4 . .
C11 C7 C8 116.61(16) . .
C11 C7 C6 118.40(16) . .
C8 C7 C6 124.99(16) . .
C9 C8 C7 119.69(16) . .
C9 C8 H8 120.2 . .
C7 C8 H8 120.2 . .
C8 C9 C10 119.67(17) . .
C8 C9 H9 120.2 . .
C10 C9 H9 120.2 . .
N1 C10 C9 121.84(16) . .
N1 C10 H10 119.1 . .
C9 C10 H10 119.1 . .
N1 C11 C7 123.48(16) . .
N1 C11 C12 116.06(15) . .
C7 C11 C12 120.45(15) . .
N2 C12 C4 123.32(16) . .
N2 C12 C11 116.48(15) . .
C4 C12 C11 120.19(15) . .
C14 C13 P1 111.75(11) . .
C14 C13 H13A 109.3 . .
P1 C13 H13A 109.3 . .
C14 C13 H13B 109.3 . .
P1 C13 H13B 109.3 . .
H13A C13 H13B 107.9 . .
C19 C14 C15 118.87(15) . .
C19 C14 C13 120.44(15) . .
C15 C14 C13 120.63(15) . .
C16 C15 C14 121.29(15) . .
C16 C15 H15 119.4 . .
C14 C15 H15 119.4 . .
C17 C16 C15 118.73(16) . .
C17 C16 C20 120.07(15) . 2_777
C15 C16 C20 121.18(15) . 2_777
C18 C17 C16 120.58(16) . .
C18 C17 H17 119.7 . .
C16 C17 H17 119.7 . .
C19 C18 C17 120.13(16) . .
C19 C18 H18 119.9 . .
C17 C18 H18 119.9 . .
C18 C19 C14 120.40(16) . .
C18 C19 H19 119.8 . .
C14 C19 H19 119.8 . .
C16 C20 P2 113.54(12) 2_777 .
C16 C20 H20A 108.9 2_777 .
P2 C20 H20A 108.9 . .
C16 C20 H20B 108.9 2_777 .
P2 C20 H20B 108.9 . .
H20A C20 H20B 107.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O2 1.9120(12) .
Cu1 O1 1.9489(12) .
Cu1 N2 2.0119(14) .
Cu1 N1 2.0282(14) .
Cu1 O3 2.2388(12) 2_677
P1 O2 1.5136(12) .
P1 O3 1.5179(12) .
P1 O4 1.5704(12) .
P1 C13 1.8122(17) .
P2 O5 1.5059(13) .
P2 O1 1.5112(12) .
P2 O6 1.5804(12) .
P2 C20 1.8117(17) .
O3 Cu1 2.2388(12) 2_677
O4 H4' 0.8200 .
O6 H6' 0.8200 .
N1 C10 1.328(2) .
N1 C11 1.359(2) .
N2 C1 1.328(2) .
N2 C12 1.359(2) .
C1 C2 1.405(2) .
C1 H1 0.9300 .
C2 C3 1.373(3) .
C2 H2 0.9300 .
C3 C4 1.412(3) .
C3 H3 0.9300 .
C4 C12 1.406(2) .
C4 C5 1.438(3) .
C5 C6 1.355(3) .
C5 H5 0.9300 .
C6 C7 1.440(3) .
C6 H6 0.9300 .
C7 C11 1.402(2) .
C7 C8 1.412(3) .
C8 C9 1.375(3) .
C8 H8 0.9300 .
C9 C10 1.405(2) .
C9 H9 0.9300 .
C10 H10 0.9300 .
C11 C12 1.433(2) .
C13 C14 1.513(2) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 C19 1.395(2) .
C14 C15 1.397(2) .
C15 C16 1.396(2) .
C15 H15 0.9300 .
C16 C17 1.394(2) .
C16 C20 1.513(2) 2_777
C17 C18 1.390(3) .
C17 H17 0.9300 .
C18 C19 1.388(3) .
C18 H18 0.9300 .
C19 H19 0.9300 .
C20 C16 1.513(2) 2_777
C20 H20A 0.9700 .
C20 H20B 0.9700 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O5 P2 O1 Cu1 -40.77(15) . .
O6 P2 O1 Cu1 87.86(14) . .
C20 P2 O1 Cu1 -162.60(12) . .
O2 Cu1 O1 P2 -90.92(13) . .
N2 Cu1 O1 P2 96.06(13) . .
N1 Cu1 O1 P2 172.02(11) . .
O3 Cu1 O1 P2 1.15(15) 2_677 .
O3 P1 O2 Cu1 69.66(11) . .
O4 P1 O2 Cu1 -166.64(9) . .
C13 P1 O2 Cu1 -53.02(12) . .
O1 Cu1 O2 P1 -10.77(10) . .
N2 Cu1 O2 P1 123.2(3) . .
N1 Cu1 O2 P1 137.80(10) . .
O3 Cu1 O2 P1 -122.80(10) 2_677 .
O2 P1 O3 Cu1 46.46(9) . 2_677
O4 P1 O3 Cu1 -75.65(8) . 2_677
C13 P1 O3 Cu1 169.88(7) . 2_677
O2 Cu1 N1 C10 3.06(15) . .
O1 Cu1 N1 C10 101.87(16) . .
N2 Cu1 N1 C10 -179.41(15) . .
O3 Cu1 N1 C10 -86.71(15) 2_677 .
O2 Cu1 N1 C11 -173.24(11) . .
O1 Cu1 N1 C11 -74.44(15) . .
N2 Cu1 N1 C11 4.29(11) . .
O3 Cu1 N1 C11 96.99(11) 2_677 .
O2 Cu1 N2 C1 -168.9(3) . .
O1 Cu1 N2 C1 -34.72(15) . .
N1 Cu1 N2 C1 176.30(15) . .
O3 Cu1 N2 C1 77.39(14) 2_677 .
O2 Cu1 N2 C12 10.5(4) . .
O1 Cu1 N2 C12 144.77(11) . .
N1 Cu1 N2 C12 -4.21(11) . .
O3 Cu1 N2 C12 -103.12(11) 2_677 .
C12 N2 C1 C2 -0.2(2) . .
Cu1 N2 C1 C2 179.25(12) . .
N2 C1 C2 C3 -1.5(3) . .
C1 C2 C3 C4 1.5(3) . .
C2 C3 C4 C12 0.1(2) . .
C2 C3 C4 C5 177.75(17) . .
C12 C4 C5 C6 0.9(3) . .
C3 C4 C5 C6 -176.75(17) . .
C4 C5 C6 C7 -0.5(3) . .
C5 C6 C7 C11 0.1(3) . .
C5 C6 C7 C8 179.26(17) . .
C11 C7 C8 C9 -0.3(2) . .
C6 C7 C8 C9 -179.49(17) . .
C7 C8 C9 C10 0.5(3) . .
C11 N1 C10 C9 -0.2(2) . .
Cu1 N1 C10 C9 -176.30(12) . .
C8 C9 C10 N1 -0.2(3) . .
C10 N1 C11 C7 0.4(2) . .
Cu1 N1 C11 C7 177.06(13) . .
C10 N1 C11 C12 179.62(15) . .
Cu1 N1 C11 C12 -3.68(18) . .
C8 C7 C11 N1 -0.1(2) . .
C6 C7 C11 N1 179.11(15) . .
C8 C7 C11 C12 -179.32(15) . .
C6 C7 C11 C12 -0.1(2) . .
C1 N2 C12 C4 2.0(2) . .
Cu1 N2 C12 C4 -177.59(13) . .
C1 N2 C12 C11 -176.96(15) . .
Cu1 N2 C12 C11 3.50(18) . .
C3 C4 C12 N2 -1.9(2) . .
C5 C4 C12 N2 -179.70(15) . .
C3 C4 C12 C11 176.98(15) . .
C5 C4 C12 C11 -0.8(2) . .
N1 C11 C12 N2 0.1(2) . .
C7 C11 C12 N2 179.43(15) . .
N1 C11 C12 C4 -178.80(14) . .
C7 C11 C12 C4 0.5(2) . .
O2 P1 C13 C14 -41.64(14) . .
O3 P1 C13 C14 -168.19(11) . .
O4 P1 C13 C14 73.70(13) . .
P1 C13 C14 C19 -79.34(18) . .
P1 C13 C14 C15 97.80(16) . .
C19 C14 C15 C16 0.4(2) . .
C13 C14 C15 C16 -176.80(15) . .
C14 C15 C16 C17 -0.6(2) . .
C14 C15 C16 C20 -179.28(15) . 2_777
C15 C16 C17 C18 0.3(3) . .
C20 C16 C17 C18 178.99(16) 2_777 .
C16 C17 C18 C19 0.2(3) . .
C17 C18 C19 C14 -0.5(3) . .
C15 C14 C19 C18 0.2(3) . .
C13 C14 C19 C18 177.35(16) . .
O5 P2 C20 C16 -53.24(14) . 2_777
O1 P2 C20 C16 72.83(13) . 2_777
O6 P2 C20 C16 -171.50(12) . 2_777
