#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/76/1517637.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_1517637
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         'C16 H14 Cu N2 O4 P, 3(H2 O)'
_chemical_formula_sum            'C16 H20 Cu N2 O7 P'
_chemical_formula_weight         446.85
_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                116.021(3)
_cell_angle_beta                 93.494(3)
_cell_angle_gamma                95.651(3)
_cell_formula_units_Z            2
_cell_length_a                   6.8782(12)
_cell_length_b                   11.792(2)
_cell_length_c                   11.808(2)
_cell_measurement_reflns_used    6382
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      27.08
_cell_measurement_theta_min      3.34
_cell_volume                     850.6(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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9097
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    1.423
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS SHELXL-97 (Sheldrick, 2008)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.107
_refine_diff_density_min         -1.204
_refine_diff_density_rms         0.176
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         2967
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0534
_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)+(0.0990P)²+4.4541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1603
_refine_ls_wR_factor_ref         0.1677
_reflns_number_gt                2546
_reflns_number_total             2967
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ICA-2013-403-63-77-3.cif
_cod_data_source_block           compound_3
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1517637
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 0.65130(9) 0.81049(5) -0.00535(6) 0.0127(2) Uani 1 1 d .
P1 P 0.45801(18) 1.04564(12) 0.17554(11) 0.0103(3) Uani 1 1 d .
O1 O 0.5197(5) 0.8545(3) -0.1259(3) 0.0158(8) Uani 1 1 d .
O2 O 0.9629(6) 0.8478(5) -0.0454(4) 0.0398(13) Uani 1 1 d .
H2A' H 0.9828 0.7883 -0.1144 0.048 Uiso 1 1 calc R
H2B' H 1.0565 0.8776 0.0153 0.048 Uiso 1 1 d R
O3 O 0.6275(5) 0.9648(3) 0.1441(3) 0.0145(8) Uani 1 1 d .
O4 O 0.2576(5) 0.9682(4) 0.1408(4) 0.0206(8) Uani 1 1 d .
O90 O 0.0141(8) 0.8965(5) 0.7276(9) 0.091(3) Uani 1 1 d D
H90A H -0.041(15) 0.943(10) 0.702(12) 0.109 Uiso 1 1 d D
H90B H 0.127(8) 0.936(9) 0.764(10) 0.109 Uiso 1 1 d D
O91 O 0.9573(14) 0.6403(7) 0.5383(6) 0.087(3) Uani 1 1 d D
H91A H 0.862(12) 0.651(10) 0.495(10) 0.104 Uiso 1 1 d D
H91B H 1.002(16) 0.718(4) 0.594(8) 0.104 Uiso 1 1 d D
O92 O 0.1710(15) 0.6956(11) 0.7716(10) 0.108(3) Uani 1 1 d D
H92A H 0.148(19) 0.662(13) 0.686(3) 0.130 Uiso 1 1 d D
H92B H 0.289(11) 0.742(12) 0.785(11) 0.130 Uiso 1 1 d D
N1 N 0.6415(6) 0.6281(4) -0.1424(4) 0.0165(9) Uani 1 1 d .
N2 N 0.7357(7) 0.7271(4) 0.1039(5) 0.0189(10) Uani 1 1 d .
C1 C 0.6005(9) 0.5822(6) -0.2671(6) 0.0263(13) Uani 1 1 d .
H1 H 0.5648 0.6381 -0.3007 0.032 Uiso 1 1 calc R
C2 C 0.6076(10) 0.4561(6) -0.3501(7) 0.0374(16) Uani 1 1 d .
H2 H 0.5828 0.4275 -0.4391 0.045 Uiso 1 1 calc R
C3 C 0.6509(10) 0.3728(6) -0.3030(7) 0.0401(18) Uani 1 1 d .
H3 H 0.6530 0.2857 -0.3594 0.048 Uiso 1 1 calc R
C4 C 0.6918(8) 0.4154(5) -0.1728(7) 0.0314(15) Uani 1 1 d .
C5 C 0.7393(9) 0.3370(6) -0.1145(8) 0.0366(17) Uani 1 1 d .
H5 H 0.7389 0.2483 -0.1654 0.044 Uiso 1 1 calc R
C6 C 0.7857(9) 0.3882(7) 0.0142(9) 0.0396(19) Uani 1 1 d .
H6 H 0.8168 0.3344 0.0514 0.048 Uiso 1 1 calc R
C7 C 0.7882(8) 0.5223(6) 0.0941(7) 0.0270(14) Uani 1 1 d .
C8 C 0.8375(9) 0.5818(7) 0.2267(7) 0.0331(16) Uani 1 1 d .
H8 H 0.8709 0.5331 0.2693 0.040 Uiso 1 1 calc R
C9 C 0.8369(9) 0.7110(7) 0.2940(7) 0.0313(15) Uani 1 1 d .
H9 H 0.8713 0.7524 0.3834 0.038 Uiso 1 1 calc R
C10 C 0.7849(8) 0.7809(6) 0.2295(6) 0.0226(12) Uani 1 1 d .
H10 H 0.7847 0.8701 0.2769 0.027 Uiso 1 1 calc R
C11 C 0.7386(7) 0.6000(5) 0.0385(6) 0.0194(12) Uani 1 1 d .
C12 C 0.6892(7) 0.5464(5) -0.0958(6) 0.0203(12) Uani 1 1 d .
C13 C 0.4956(9) 1.1400(5) 0.3478(5) 0.0187(11) Uani 1 1 d .
H13A H 0.6221 1.1971 0.3706 0.022 Uiso 1 1 calc R
H13B H 0.3902 1.1948 0.3731 0.022 Uiso 1 1 calc R
C14 C 0.4978(9) 1.0667(5) 0.4249(5) 0.0210(12) Uani 1 1 d .
C15 C 0.6739(9) 1.0538(5) 0.4802(5) 0.0223(12) Uani 1 1 d .
H15 H 0.7947 1.0904 0.4672 0.027 Uiso 1 1 calc R
C16 C 0.6770(9) 0.9883(5) 0.5541(5) 0.0231(13) Uani 1 1 d .
H16 H 0.7993 0.9812 0.5905 0.028 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
O1 Cu1 O3 96.68(14) . .
O1 Cu1 N2 165.75(17) . .
O3 Cu1 N2 90.67(17) . .
O1 Cu1 N1 90.14(16) . .
O3 Cu1 N1 166.90(17) . .
N2 Cu1 N1 80.41(19) . .
O1 Cu1 O2 97.46(17) . .
O3 Cu1 O2 102.68(16) . .
N2 Cu1 O2 92.78(19) . .
N1 Cu1 O2 87.43(17) . .
O4 P1 O1 114.2(2) . 2_675
O4 P1 O3 113.8(2) . .
O1 P1 O3 111.3(2) 2_675 .
O4 P1 C13 107.8(2) . .
O1 P1 C13 103.7(2) 2_675 .
O3 P1 C13 104.9(2) . .
P1 O1 Cu1 140.1(2) 2_675 .
Cu1 O2 H2A' 109.5 . .
Cu1 O2 H2B' 119.5 . .
H2A' O2 H2B' 117.4 . .
P1 O3 Cu1 129.7(2) . .
H90A O90 H90B 107(5) . .
H91A O91 H91B 102(5) . .
H92A O92 H92B 100(4) . .
C1 N1 C12 117.9(5) . .
C1 N1 Cu1 128.8(4) . .
C12 N1 Cu1 113.3(4) . .
C10 N2 C11 117.5(5) . .
C10 N2 Cu1 128.4(4) . .
C11 N2 Cu1 114.0(4) . .
N1 C1 C2 122.6(6) . .
N1 C1 H1 118.7 . .
C2 C1 H1 118.7 . .
C3 C2 C1 119.5(7) . .
C3 C2 H2 120.3 . .
C1 C2 H2 120.3 . .
C2 C3 C4 120.2(6) . .
C2 C3 H3 119.9 . .
C4 C3 H3 119.9 . .
C3 C4 C12 116.3(6) . .
C3 C4 C5 124.6(6) . .
C12 C4 C5 119.0(7) . .
C6 C5 C4 120.6(6) . .
C6 C5 H5 119.7 . .
C4 C5 H5 119.7 . .
C5 C6 C7 121.2(6) . .
C5 C6 H6 119.4 . .
C7 C6 H6 119.4 . .
C11 C7 C8 116.9(6) . .
C11 C7 C6 118.8(6) . .
C8 C7 C6 124.3(6) . .
C9 C8 C7 119.6(5) . .
C9 C8 H8 120.2 . .
C7 C8 H8 120.2 . .
C8 C9 C10 119.3(6) . .
C8 C9 H9 120.3 . .
C10 C9 H9 120.3 . .
N2 C10 C9 122.6(6) . .
N2 C10 H10 118.7 . .
C9 C10 H10 118.7 . .
N2 C11 C7 124.1(6) . .
N2 C11 C12 115.9(5) . .
C7 C11 C12 120.0(5) . .
N1 C12 C4 123.3(6) . .
N1 C12 C11 116.4(5) . .
C4 C12 C11 120.3(5) . .
C14 C13 P1 116.4(4) . .
C14 C13 H13A 108.2 . .
P1 C13 H13A 108.2 . .
C14 C13 H13B 108.2 . .
P1 C13 H13B 108.2 . .
H13A C13 H13B 107.3 . .
C15 C14 C16 117.7(5) . 2_676
C15 C14 C13 121.2(5) . .
C16 C14 C13 121.1(5) 2_676 .
C14 C15 C16 121.5(6) . .
C14 C15 H15 119.2 . .
C16 C15 H15 119.2 . .
C15 C16 C14 120.8(6) . 2_676
C15 C16 H16 119.6 . .
C14 C16 H16 119.6 2_676 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.924(4) .
Cu1 O3 1.931(3) .
Cu1 N2 2.026(4) .
Cu1 N1 2.038(4) .
Cu1 O2 2.265(4) .
P1 O4 1.502(4) .
P1 O1 1.528(4) 2_675
P1 O3 1.538(4) .
P1 C13 1.826(5) .
O1 P1 1.528(4) 2_675
O2 H2A' 0.8400 .
O2 H2B' 0.8543 .
O90 H90A 0.85(2) .
O90 H90B 0.85(2) .
O91 H91A 0.87(2) .
O91 H91B 0.87(2) .
O92 H92A 0.90(2) .
O92 H92B 0.90(2) .
N1 C1 1.327(7) .
N1 C12 1.358(7) .
N2 C10 1.337(8) .
N2 C11 1.355(7) .
C1 C2 1.384(8) .
C1 H1 0.9500 .
C2 C3 1.371(10) .
C2 H2 0.9500 .
C3 C4 1.391(11) .
C3 H3 0.9500 .
C4 C12 1.410(8) .
C4 C5 1.423(10) .
C5 C6 1.369(11) .
C5 H5 0.9500 .
C6 C7 1.440(10) .
C6 H6 0.9500 .
C7 C11 1.397(8) .
C7 C8 1.407(10) .
C8 C9 1.375(10) .
C8 H8 0.9500 .
C9 C10 1.401(8) .
C9 H9 0.9500 .
C10 H10 0.9500 .
C11 C12 1.428(9) .
C13 C14 1.507(7) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.394(9) .
C14 C16 1.397(9) 2_676
C15 C16 1.396(8) .
C15 H15 0.9500 .
C16 C14 1.397(9) 2_676
C16 H16 0.9500 .
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
O3 Cu1 O1 P1 62.4(4) . 2_675
N2 Cu1 O1 P1 -177.0(6) . 2_675
N1 Cu1 O1 P1 -128.8(4) . 2_675
O2 Cu1 O1 P1 -41.4(4) . 2_675
O4 P1 O3 Cu1 42.9(3) . .
O1 P1 O3 Cu1 -87.9(3) 2_675 .
C13 P1 O3 Cu1 160.5(3) . .
O1 Cu1 O3 P1 36.5(3) . .
N2 Cu1 O3 P1 -131.3(3) . .
N1 Cu1 O3 P1 -84.5(7) . .
O2 Cu1 O3 P1 135.7(3) . .
O1 Cu1 N1 C1 13.6(5) . .
O3 Cu1 N1 C1 135.2(7) . .
N2 Cu1 N1 C1 -177.1(5) . .
O2 Cu1 N1 C1 -83.8(5) . .
O1 Cu1 N1 C12 -168.2(4) . .
O3 Cu1 N1 C12 -46.6(9) . .
N2 Cu1 N1 C12 1.1(3) . .
O2 Cu1 N1 C12 94.4(4) . .
O1 Cu1 N2 C10 -131.8(7) . .
O3 Cu1 N2 C10 -10.5(5) . .
N1 Cu1 N2 C10 179.1(5) . .
O2 Cu1 N2 C10 92.2(5) . .
O1 Cu1 N2 C11 47.3(9) . .
O3 Cu1 N2 C11 168.6(4) . .
N1 Cu1 N2 C11 -1.8(4) . .
O2 Cu1 N2 C11 -88.7(4) . .
C12 N1 C1 C2 -1.0(8) . .
Cu1 N1 C1 C2 177.1(5) . .
N1 C1 C2 C3 2.7(10) . .
C1 C2 C3 C4 -1.5(10) . .
C2 C3 C4 C12 -1.1(9) . .
C2 C3 C4 C5 -179.6(6) . .
C3 C4 C5 C6 177.2(6) . .
C12 C4 C5 C6 -1.2(9) . .
C4 C5 C6 C7 -0.1(9) . .
C5 C6 C7 C11 1.2(8) . .
C5 C6 C7 C8 -178.9(6) . .
C11 C7 C8 C9 -0.7(8) . .
C6 C7 C8 C9 179.4(5) . .
C7 C8 C9 C10 0.7(9) . .
C11 N2 C10 C9 -0.5(8) . .
Cu1 N2 C10 C9 178.6(4) . .
C8 C9 C10 N2 -0.1(9) . .
C10 N2 C11 C7 0.5(8) . .
Cu1 N2 C11 C7 -178.7(4) . .
C10 N2 C11 C12 -178.7(5) . .
Cu1 N2 C11 C12 2.1(6) . .
C8 C7 C11 N2 0.1(8) . .
C6 C7 C11 N2 180.0(5) . .
C8 C7 C11 C12 179.3(5) . .
C6 C7 C11 C12 -0.9(8) . .
C1 N1 C12 C4 -1.8(8) . .
Cu1 N1 C12 C4 179.7(4) . .
C1 N1 C12 C11 178.1(5) . .
Cu1 N1 C12 C11 -0.3(6) . .
C3 C4 C12 N1 2.9(8) . .
C5 C4 C12 N1 -178.5(5) . .
C3 C4 C12 C11 -177.0(5) . .
C5 C4 C12 C11 1.6(8) . .
N2 C11 C12 N1 -1.2(7) . .
C7 C11 C12 N1 179.6(5) . .
N2 C11 C12 C4 178.7(5) . .
C7 C11 C12 C4 -0.5(8) . .
O4 P1 C13 C14 63.1(5) . .
O1 P1 C13 C14 -175.4(4) 2_675 .
O3 P1 C13 C14 -58.5(5) . .
P1 C13 C14 C15 102.2(5) . .
P1 C13 C14 C16 -79.3(6) . 2_676
C16 C14 C15 C16 0.0(9) 2_676 .
C13 C14 C15 C16 178.6(5) . .
C14 C15 C16 C14 0.0(9) . 2_676
