#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/91/4509112.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_4509112
loop_
_publ_author_name
'Sonnauer, Andreas'
'Feyand, Mark'
'Stock, Norbert'
_publ_section_title
;
 Synthesis of 4-Phosphonobutanesulfonic Acid and Systematic Investigation
 of Copper Phosphonatobutanesulfonates by High-Throughput Methods
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              586
_journal_paper_doi               10.1021/cg8008865
_journal_volume                  9
_journal_year                    2009
_chemical_formula_moiety         'C4 H12.3 Cu1.50 O8.15 P S'
_chemical_formula_sum            'C4 H12.3 Cu1.5 O8.15 P S'
_chemical_formula_weight         349.09
_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                108.388(11)
_cell_angle_beta                 95.656(11)
_cell_angle_gamma                93.521(11)
_cell_formula_units_Z            2
_cell_length_a                   5.1197(5)
_cell_length_b                   10.5328(10)
_cell_length_c                   10.8003(10)
_cell_measurement_temperature    293(2)
_cell_volume                     547.33(10)
_computing_data_reduction        XPrep
_computing_molecular_graphics    Diamond
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'STOE IPDS I'
_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  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_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            5965
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    3.300
_exptl_absorpt_correction_T_max  0.6506
_exptl_absorpt_correction_T_min  0.5043
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 Absorption correction with XRed, rev 1.09, STOE (Darmstadt, Germany) 
;
_exptl_crystal_colour            'lightly blue'
_exptl_crystal_density_diffrn    2.117
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             351
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.756
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2531
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0286
_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)+(0.0482P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0750
_reflns_number_gt                2103
_reflns_number_total             2531
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg8008865sup1.cif
_cod_data_source_block           '[Cu1.5(O3P-C4H8-SO3)(H2O)]1.15H2O'
_cod_original_cell_volume        547.3(1)
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C4 H12.3 Cu1.50 O8.15 P S'
_cod_database_code               4509112
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 0.0000 0.0000 0.0000 0.01033(13) Uani 1 2 d S
Cu2 Cu 0.47353(7) 0.22474(3) -0.02663(3) 0.01066(11) Uani 1 1 d .
S1 S 0.91877(13) 0.30504(6) -0.15562(6) 0.01142(15) Uani 1 1 d .
P1 P 0.55993(13) 0.07763(6) -0.82411(6) 0.00768(15) Uani 1 1 d .
O1 O 0.3461(4) 0.11254(17) -0.91804(17) 0.0096(4) Uani 1 1 d .
O2 O 0.5068(4) -0.06704(18) -0.82730(18) 0.0150(4) Uani 1 1 d .
O3 O 0.8337(4) 0.11125(19) -0.85853(18) 0.0128(4) Uani 1 1 d .
O4 O 0.6492(4) 0.33330(19) -0.12283(19) 0.0135(4) Uani 1 1 d .
O5 O 1.0738(5) 0.4245(2) -0.1535(2) 0.0241(5) Uani 1 1 d .
O6 O 1.0415(4) 0.2341(2) -0.0716(2) 0.0185(4) Uani 1 1 d .
O7 O 0.5091(5) 0.3820(2) 0.1304(2) 0.0215(5) Uani 1 1 d .
H5 H 0.392(9) 0.389(4) 0.179(4) 0.033(12) Uiso 1 1 d .
H6 H 0.565(11) 0.446(5) 0.139(5) 0.052(16) Uiso 1 1 d .
O8 O 0.0975(6) 0.3756(3) 0.2609(3) 0.0325(6) Uani 1 1 d .
H7 H -0.003(15) 0.408(8) 0.224(7) 0.10(3) Uiso 1 1 d .
H8 H 0.028(12) 0.287(7) 0.219(6) 0.074(18) Uiso 1 1 d .
C1 C 0.5422(6) 0.1828(3) -0.6591(3) 0.0144(5) Uani 1 1 d .
H1B H 0.5888 0.2757 -0.6521 0.017 Uiso 1 1 calc R
H1A H 0.3621 0.1751 -0.6396 0.017 Uiso 1 1 calc R
C2 C 0.7255(6) 0.1461(3) -0.5572(3) 0.0197(6) Uani 1 1 d .
H2B H 0.6719 0.0551 -0.5604 0.024 Uiso 1 1 calc R
H2A H 0.9040 0.1483 -0.5799 0.024 Uiso 1 1 calc R
C3 C 0.7232(7) 0.2409(3) -0.4178(3) 0.0231(7) Uani 1 1 d .
H3B H 0.7946 0.3305 -0.4114 0.028 Uiso 1 1 calc R
H3A H 0.5432 0.2455 -0.3971 0.028 Uiso 1 1 calc R
C4 C 0.8877(6) 0.1916(3) -0.3190(3) 0.0169(6) Uani 1 1 d .
H4B H 1.0623 0.1784 -0.3456 0.020 Uiso 1 1 calc R
H4A H 0.8064 0.1053 -0.3207 0.020 Uiso 1 1 calc R
O9 O 0.764(3) 0.5406(15) -0.5346(13) 0.023(3) Uani 0.15 1 d P
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'
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'
S S 0.1246 0.1234 '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
O3 Cu1 O3 180.00(13) 2_654 1_456
O3 Cu1 O1 91.12(8) 2_654 1_556
O3 Cu1 O1 88.88(8) 1_456 1_556
O3 Cu1 O1 88.88(8) 2_654 2_554
O3 Cu1 O1 91.12(8) 1_456 2_554
O1 Cu1 O1 180.00(16) 1_556 2_554
O3 Cu1 O6 96.83(7) 2_654 1_455
O3 Cu1 O6 83.17(7) 1_456 1_455
O1 Cu1 O6 68.90(7) 1_556 1_455
O1 Cu1 O6 111.10(7) 2_554 1_455
O2 Cu2 O7 171.23(10) 2_654 .
O2 Cu2 O4 88.65(8) 2_654 .
O7 Cu2 O4 90.13(10) . .
O2 Cu2 O1 91.46(8) 2_654 1_556
O7 Cu2 O1 88.56(9) . 1_556
O4 Cu2 O1 172.09(8) . 1_556
O2 Cu2 O6 95.26(9) 2_654 1_455
O7 Cu2 O6 93.43(10) . 1_455
O4 Cu2 O6 105.55(8) . 1_455
O1 Cu2 O6 82.31(8) 1_556 1_455
O5 S1 O6 114.08(13) . .
O5 S1 O4 111.67(13) . .
O6 S1 O4 109.99(12) . .
O5 S1 C4 107.11(14) . .
O6 S1 C4 106.03(13) . .
O4 S1 C4 107.56(14) . .
O2 P1 O3 114.07(12) . .
O2 P1 O1 110.72(11) . .
O3 P1 O1 109.01(10) . .
O2 P1 C1 107.04(12) . .
O3 P1 C1 107.13(13) . .
O1 P1 C1 108.67(12) . .
P1 O1 Cu1 125.07(10) . 1_554
P1 O1 Cu2 116.79(11) . 1_554
Cu1 O1 Cu2 112.88(8) 1_554 1_554
P1 O2 Cu2 126.31(12) . 2_654
P1 O3 Cu1 125.38(12) . 1_654
S1 O4 Cu2 117.97(11) . .
S1 O6 Cu2 126.03(13) . 1_655
C2 C1 P1 112.70(19) . .
C3 C2 C1 112.7(2) . .
C4 C3 C2 110.4(2) . .
C3 C4 S1 113.0(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O3 1.919(2) 2_654
Cu1 O3 1.919(2) 1_456
Cu1 O1 2.025(2) 1_556
Cu1 O1 2.025(2) 2_554
Cu1 O6 2.810(2) 1_455
Cu2 O2 1.912(2) 2_654
Cu2 O7 1.945(2) .
Cu2 O4 2.0008(19) .
Cu2 O1 2.0319(18) 1_556
Cu2 O6 2.232(2) 1_455
S1 O5 1.439(2) .
S1 O6 1.4658(19) .
S1 O4 1.483(2) .
S1 C4 1.777(3) .
P1 O2 1.5203(19) .
P1 O3 1.534(2) .
P1 O1 1.5584(18) .
P1 C1 1.792(3) .
O1 Cu1 2.025(2) 1_554
O1 Cu2 2.0319(18) 1_554
O2 Cu2 1.912(2) 2_654
O3 Cu1 1.919(2) 1_654
O6 Cu2 2.232(2) 1_655
O8 O9 2.808(14) 2_665
C1 C2 1.533(4) .
C2 C3 1.524(4) .
C3 C4 1.531(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
O7 H6 O5 0.69(5) 2.19(6) 2.795(3) 147(5) 2_765
O7 H5 O8 0.83(5) 1.84(5) 2.657(4) 168(4) 1
O8 H7 O5 0.78(7) 2.17(7) 2.848(4) 146(8) 2_665
O8 H8 O3 0.93(7) 1.94(7) 2.859(4) 171(6) 1_456
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 P1 O1 Cu1 13.52(17) . 1_554
O3 P1 O1 Cu1 139.79(12) . 1_554
C1 P1 O1 Cu1 -103.77(15) . 1_554
O2 P1 O1 Cu2 -138.94(11) . 1_554
O3 P1 O1 Cu2 -12.67(14) . 1_554
C1 P1 O1 Cu2 103.77(14) . 1_554
O3 P1 O2 Cu2 -56.49(18) . 2_654
O1 P1 O2 Cu2 66.90(18) . 2_654
C1 P1 O2 Cu2 -174.81(15) . 2_654
O2 P1 O3 Cu1 43.69(17) . 1_654
O1 P1 O3 Cu1 -80.63(15) . 1_654
C1 P1 O3 Cu1 161.95(13) . 1_654
O5 S1 O4 Cu2 -147.34(13) . .
O6 S1 O4 Cu2 -19.63(17) . .
C4 S1 O4 Cu2 95.41(15) . .
O2 Cu2 O4 S1 -61.68(14) 2_654 .
O7 Cu2 O4 S1 109.64(15) . .
O6 Cu2 O4 S1 -156.76(12) 1_455 .
O5 S1 O6 Cu2 -32.0(2) . 1_655
O4 S1 O6 Cu2 -158.37(13) . 1_655
C4 S1 O6 Cu2 85.62(18) . 1_655
O2 P1 C1 C2 54.4(2) . .
O3 P1 C1 C2 -68.4(2) . .
O1 P1 C1 C2 174.0(2) . .
P1 C1 C2 C3 176.5(2) . .
C1 C2 C3 C4 174.4(3) . .
C2 C3 C4 S1 174.7(2) . .
O5 S1 C4 C3 -66.9(3) . .
O6 S1 C4 C3 170.9(2) . .
O4 S1 C4 C3 53.2(3) . .
