#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/76/1517642.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_1517642
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         'C18 H18 Cu N2 O6 P2, 2(H2 O)'
_chemical_formula_sum            'C18 H22 Cu N2 O8 P2'
_chemical_formula_weight         519.86
_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                110.062(2)
_cell_angle_beta                 108.237(2)
_cell_angle_gamma                91.260(2)
_cell_formula_units_Z            2
_cell_length_a                   9.9436(13)
_cell_length_b                   10.0660(14)
_cell_length_c                   11.3028(15)
_cell_measurement_reflns_used    1927
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      24.98
_cell_measurement_theta_min      2.37
_cell_volume                     998.6(2)
_computing_cell_refinement       'Bruker SMART (Bruker, 2002)'
_computing_data_collection       'Bruker SMART (Bruker, 2002)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2002)'
_computing_molecular_graphics    'CrystalMaker (Palmer, 2006)'
_computing_publication_material  'Bruker SHELXTL (Bruker, 2002)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX CCD area detector'
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0910
_diffrn_reflns_av_sigmaI/netI    0.1064
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7492
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.04
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0.001
_exptl_absorpt_coefficient_mu    1.306
_exptl_absorpt_correction_T_max  0.9496
_exptl_absorpt_correction_T_min  0.7802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS SHELXL-97 (Sheldrick, 1997)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             534
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.555
_refine_diff_density_min         -0.965
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         3501
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0179P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1108
_reflns_number_gt                2606
_reflns_number_total             3501
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ICA-2013-403-63-77-8.cif
_cod_data_source_block           compound_8
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1517642
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 0.24705(6) 0.13110(6) 0.04477(6) 0.01477(18) Uani 1 1 d .
P1 P 0.31786(12) 0.41617(14) 0.34623(12) 0.0171(3) Uani 1 1 d .
P2 P 0.06563(12) -0.01222(14) 0.16699(12) 0.0149(3) Uani 1 1 d .
O1 O 0.0657(3) 0.1253(3) -0.0932(3) 0.0171(8) Uani 1 1 d .
O2 O 0.1682(3) -0.0147(3) 0.0915(3) 0.0150(7) Uani 1 1 d .
O3 O 0.2138(3) 0.3114(3) 0.2149(3) 0.0180(8) Uani 1 1 d .
O4 O 0.0164(3) 0.1382(3) 0.2129(3) 0.0179(8) Uani 1 1 d .
H4' H 0.0759 0.1991 0.2173 0.021 Uiso 1 1 calc R
O5 O 0.4470(3) 0.4767(4) 0.3224(3) 0.0212(8) Uani 1 1 d .
H5' H 0.5120 0.5154 0.3943 0.025 Uiso 1 1 calc R
O6 O 0.3662(3) 0.3496(3) 0.4537(3) 0.0211(8) Uani 1 1 d .
O90 O 0.5006(12) 0.8459(11) 0.4407(13) 0.180(4) Uani 1 1 d D
H90A H 0.436(12) 0.766(9) 0.386(12) 0.216 Uiso 1 1 d D
H90B H 0.563(12) 0.807(13) 0.495(14) 0.216 Uiso 1 1 d D
O91 O 0.0449(7) 0.6111(6) 0.9654(5) 0.0760(17) Uani 1 1 d D
H91A H 0.089(7) 0.617(8) 0.915(5) 0.091 Uiso 1 1 d D
H91B H 0.083(8) 0.668(7) 1.046(3) 0.091 Uiso 1 1 d D
N1 N 0.3553(4) 0.2366(4) -0.0261(4) 0.0163(9) Uani 1 1 d .
N2 N 0.4471(4) 0.1152(4) 0.1472(4) 0.0144(9) Uani 1 1 d .
C1 C 0.2986(5) 0.2938(5) -0.1182(5) 0.0190(11) Uani 1 1 d .
H1 H 0.2002 0.2942 -0.1473 0.023 Uiso 1 1 calc R
C2 C 0.3804(5) 0.3520(5) -0.1716(5) 0.0245(13) Uani 1 1 d .
H2 H 0.3376 0.3915 -0.2351 0.029 Uiso 1 1 calc R
C3 C 0.5261(5) 0.3513(5) -0.1302(5) 0.0259(13) Uani 1 1 d .
H3 H 0.5826 0.3887 -0.1664 0.031 Uiso 1 1 calc R
C4 C 0.5868(5) 0.2945(5) -0.0348(5) 0.0214(12) Uani 1 1 d .
H4 H 0.6852 0.2951 -0.0039 0.026 Uiso 1 1 calc R
C5 C 0.4996(5) 0.2364(5) 0.0147(4) 0.0150(11) Uani 1 1 d .
C6 C 0.5517(5) 0.1695(5) 0.1158(4) 0.0149(11) Uani 1 1 d .
C7 C 0.6943(5) 0.1583(5) 0.1732(5) 0.0180(11) Uani 1 1 d .
H7 H 0.7645 0.1919 0.1479 0.022 Uiso 1 1 calc R
C8 C 0.7304(5) 0.0963(5) 0.2686(5) 0.0195(12) Uani 1 1 d .
H8 H 0.8255 0.0889 0.3092 0.023 Uiso 1 1 calc R
C9 C 0.6245(5) 0.0456(5) 0.3029(5) 0.0199(12) Uani 1 1 d .
H9 H 0.6472 0.0053 0.3682 0.024 Uiso 1 1 calc R
C10 C 0.4839(5) 0.0552(5) 0.2391(4) 0.0193(11) Uani 1 1 d .
H10 H 0.4123 0.0187 0.2611 0.023 Uiso 1 1 calc R
C11 C 0.1646(5) -0.0375(6) 0.3199(4) 0.0186(12) Uani 1 1 d .
H11A H 0.1915 -0.1328 0.2972 0.022 Uiso 1 1 calc R
H11B H 0.2520 0.0305 0.3652 0.022 Uiso 1 1 calc R
C12 C 0.0814(5) -0.0192(5) 0.4152(4) 0.0174(11) Uani 1 1 d .
C13 C -0.0014(4) -0.1354(5) 0.4122(4) 0.0159(11) Uani 1 1 d .
H13 H -0.0028 -0.2267 0.3529 0.019 Uiso 1 1 calc R
C14 C -0.0815(5) -0.1164(5) 0.4964(4) 0.0162(11) Uani 1 1 d .
H14 H -0.1354 -0.1950 0.4935 0.019 Uiso 1 1 calc R
C15 C 0.2301(5) 0.5666(5) 0.4104(5) 0.0231(12) Uani 1 1 d .
H15A H 0.3013 0.6403 0.4855 0.028 Uiso 1 1 calc R
H15B H 0.1920 0.6055 0.3411 0.028 Uiso 1 1 calc R
C16 C 0.1092(5) 0.5325(5) 0.4560(5) 0.0215(12) Uani 1 1 d .
C17 C 0.1403(5) 0.5341(5) 0.5850(5) 0.0198(11) Uani 1 1 d .
H17 H 0.2349 0.5560 0.6425 0.024 Uiso 1 1 calc R
C18 C 0.0335(5) 0.5037(5) 0.6293(5) 0.0220(12) Uani 1 1 d .
H18 H 0.0565 0.5074 0.7167 0.026 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'
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'
H H 0.0000 0.0000 '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 93.61(12) . .
O2 Cu1 N1 164.04(15) . .
O1 Cu1 N1 91.26(13) . .
O2 Cu1 N2 91.26(14) . .
O1 Cu1 N2 166.11(15) . .
N1 Cu1 N2 80.75(15) . .
O2 Cu1 O3 92.61(12) . .
O1 Cu1 O3 96.49(12) . .
N1 Cu1 O3 101.93(14) . .
N2 Cu1 O3 96.27(13) . .
O3 P1 O6 112.25(18) . .
O3 P1 O5 110.11(18) . .
O6 P1 O5 111.47(18) . .
O3 P1 C15 108.9(2) . .
O6 P1 C15 107.2(2) . .
O5 P1 C15 106.6(2) . .
O1 P2 O2 115.49(18) 2 .
O1 P2 O4 108.82(18) 2 .
O2 P2 O4 111.26(19) . .
O1 P2 C11 108.2(2) 2 .
O2 P2 C11 107.10(19) . .
O4 P2 C11 105.5(2) . .
P2 O1 Cu1 130.71(19) 2 .
P2 O2 Cu1 132.3(2) . .
P1 O3 Cu1 132.05(19) . .
P2 O4 H4' 109.5 . .
P1 O5 H5' 109.5 . .
H90A O90 H90B 99(4) . .
H91A O91 H91B 114(5) . .
C1 N1 C5 117.8(4) . .
C1 N1 Cu1 126.3(3) . .
C5 N1 Cu1 115.5(3) . .
C10 N2 C6 118.9(4) . .
C10 N2 Cu1 126.0(3) . .
C6 N2 Cu1 115.2(3) . .
N1 C1 C2 122.5(5) . .
N1 C1 H1 118.7 . .
C2 C1 H1 118.7 . .
C3 C2 C1 119.4(5) . .
C3 C2 H2 120.3 . .
C1 C2 H2 120.3 . .
C2 C3 C4 119.1(5) . .
C2 C3 H3 120.5 . .
C4 C3 H3 120.5 . .
C3 C4 C5 119.2(5) . .
C3 C4 H4 120.4 . .
C5 C4 H4 120.4 . .
N1 C5 C4 122.0(4) . .
N1 C5 C6 113.7(4) . .
C4 C5 C6 124.3(4) . .
N2 C6 C7 121.3(4) . .
N2 C6 C5 114.5(4) . .
C7 C6 C5 124.2(4) . .
C8 C7 C6 119.0(4) . .
C8 C7 H7 120.5 . .
C6 C7 H7 120.5 . .
C9 C8 C7 119.4(4) . .
C9 C8 H8 120.3 . .
C7 C8 H8 120.3 . .
C8 C9 C10 119.1(4) . .
C8 C9 H9 120.4 . .
C10 C9 H9 120.4 . .
N2 C10 C9 122.3(4) . .
N2 C10 H10 118.8 . .
C9 C10 H10 118.8 . .
C12 C11 P2 113.4(3) . .
C12 C11 H11A 108.9 . .
P2 C11 H11A 108.9 . .
C12 C11 H11B 108.9 . .
P2 C11 H11B 108.9 . .
H11A C11 H11B 107.7 . .
C14 C12 C13 118.7(5) 2_556 .
C14 C12 C11 119.6(4) 2_556 .
C13 C12 C11 121.6(5) . .
C14 C13 C12 121.1(5) . .
C14 C13 H13 119.5 . .
C12 C13 H13 119.5 . .
C12 C14 C13 120.2(5) 2_556 .
C12 C14 H14 119.9 2_556 .
C13 C14 H14 119.9 . .
C16 C15 P1 115.1(3) . .
C16 C15 H15A 108.5 . .
P1 C15 H15A 108.5 . .
C16 C15 H15B 108.5 . .
P1 C15 H15B 108.5 . .
H15A C15 H15B 107.5 . .
C17 C16 C18 118.3(4) . 2_566
C17 C16 C15 119.6(4) . .
C18 C16 C15 122.1(5) 2_566 .
C18 C17 C16 121.0(5) . .
C18 C17 H17 119.5 . .
C16 C17 H17 119.5 . .
C17 C18 C16 120.7(5) . 2_566
C17 C18 H18 119.7 . .
C16 C18 H18 119.7 2_566 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O2 1.946(3) .
Cu1 O1 1.965(3) .
Cu1 N1 2.000(4) .
Cu1 N2 2.006(4) .
Cu1 O3 2.266(3) .
P1 O3 1.517(3) .
P1 O6 1.537(3) .
P1 O5 1.545(3) .
P1 C15 1.811(5) .
P2 O1 1.516(3) 2
P2 O2 1.516(3) .
P2 O4 1.566(4) .
P2 C11 1.808(4) .
O1 P2 1.516(3) 2
O4 H4' 0.8200 .
O5 H5' 0.8200 .
O90 H90A 0.91(2) .
O90 H90B 0.92(2) .
O91 H91A 0.84(2) .
O91 H91B 0.84(2) .
N1 C1 1.339(6) .
N1 C5 1.363(6) .
N2 C10 1.335(6) .
N2 C6 1.358(6) .
C1 C2 1.378(7) .
C1 H1 0.9300 .
C2 C3 1.377(7) .
C2 H2 0.9300 .
C3 C4 1.373(7) .
C3 H3 0.9300 .
C4 C5 1.384(7) .
C4 H4 0.9300 .
C5 C6 1.483(6) .
C6 C7 1.388(6) .
C7 C8 1.382(6) .
C7 H7 0.9300 .
C8 C9 1.373(7) .
C8 H8 0.9300 .
C9 C10 1.381(6) .
C9 H9 0.9300 .
C10 H10 0.9300 .
C11 C12 1.519(6) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C14 1.388(7) 2_556
C12 C13 1.399(6) .
C13 C14 1.391(7) .
C13 H13 0.9300 .
C14 C12 1.388(7) 2_556
C14 H14 0.9300 .
C15 C16 1.524(7) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C17 1.386(7) .
C16 C18 1.398(6) 2_566
C17 C18 1.377(7) .
C17 H17 0.9300 .
C18 C16 1.398(6) 2_566
C18 H18 0.9300 .
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
O2 Cu1 O1 P2 -19.0(3) . 2
N1 Cu1 O1 P2 145.8(3) . 2
N2 Cu1 O1 P2 91.3(6) . 2
O3 Cu1 O1 P2 -112.1(3) . 2
O1 P2 O2 Cu1 125.2(2) 2 .
O4 P2 O2 Cu1 0.5(3) . .
C11 P2 O2 Cu1 -114.3(3) . .
O1 Cu1 O2 P2 -72.9(2) . .
N1 Cu1 O2 P2 179.6(4) . .
N2 Cu1 O2 P2 120.1(2) . .
O3 Cu1 O2 P2 23.8(2) . .
O6 P1 O3 Cu1 -79.8(3) . .
O5 P1 O3 Cu1 45.0(3) . .
C15 P1 O3 Cu1 161.6(2) . .
O2 Cu1 O3 P1 108.2(2) . .
O1 Cu1 O3 P1 -157.9(2) . .
N1 Cu1 O3 P1 -65.2(3) . .
N2 Cu1 O3 P1 16.6(3) . .
O2 Cu1 N1 C1 117.7(5) . .
O1 Cu1 N1 C1 9.9(4) . .
N2 Cu1 N1 C1 178.5(4) . .
O3 Cu1 N1 C1 -87.0(4) . .
O2 Cu1 N1 C5 -55.3(7) . .
O1 Cu1 N1 C5 -163.1(4) . .
N2 Cu1 N1 C5 5.5(3) . .
O3 Cu1 N1 C5 100.0(3) . .
O2 Cu1 N2 C10 -17.0(4) . .
O1 Cu1 N2 C10 -127.5(6) . .
N1 Cu1 N2 C10 176.9(4) . .
O3 Cu1 N2 C10 75.8(4) . .
O2 Cu1 N2 C6 161.9(3) . .
O1 Cu1 N2 C6 51.3(8) . .
N1 Cu1 N2 C6 -4.2(3) . .
O3 Cu1 N2 C6 -105.3(3) . .
C5 N1 C1 C2 -0.3(7) . .
Cu1 N1 C1 C2 -173.2(4) . .
N1 C1 C2 C3 0.4(8) . .
C1 C2 C3 C4 -1.1(8) . .
C2 C3 C4 C5 1.6(8) . .
C1 N1 C5 C4 0.8(7) . .
Cu1 N1 C5 C4 174.5(4) . .
C1 N1 C5 C6 -179.4(4) . .
Cu1 N1 C5 C6 -5.8(5) . .
C3 C4 C5 N1 -1.5(8) . .
C3 C4 C5 C6 178.8(5) . .
C10 N2 C6 C7 2.7(7) . .
Cu1 N2 C6 C7 -176.2(4) . .
C10 N2 C6 C5 -178.7(4) . .
Cu1 N2 C6 C5 2.3(5) . .
N1 C5 C6 N2 2.2(6) . .
C4 C5 C6 N2 -178.0(5) . .
N1 C5 C6 C7 -179.2(4) . .
C4 C5 C6 C7 0.5(8) . .
N2 C6 C7 C8 -2.9(7) . .
C5 C6 C7 C8 178.6(4) . .
C6 C7 C8 C9 0.9(7) . .
C7 C8 C9 C10 1.3(7) . .
C6 N2 C10 C9 -0.4(7) . .
Cu1 N2 C10 C9 178.4(4) . .
C8 C9 C10 N2 -1.6(8) . .
O1 P2 C11 C12 -62.1(4) 2 .
O2 P2 C11 C12 172.8(3) . .
O4 P2 C11 C12 54.2(4) . .
P2 C11 C12 C14 -85.0(5) . 2_556
P2 C11 C12 C13 92.0(5) . .
C14 C12 C13 C14 -0.5(7) 2_556 .
C11 C12 C13 C14 -177.5(4) . .
C12 C13 C14 C12 0.5(7) . 2_556
O3 P1 C15 C16 68.0(4) . .
O6 P1 C15 C16 -53.7(4) . .
O5 P1 C15 C16 -173.2(3) . .
P1 C15 C16 C17 85.4(5) . .
P1 C15 C16 C18 -93.2(5) . 2_566
C18 C16 C17 C18 -1.3(8) 2_566 .
C15 C16 C17 C18 -180.0(5) . .
C16 C17 C18 C16 1.4(8) . 2_566
