#------------------------------------------------------------------------------
#$Date: 2016-03-23 02:35:23 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179191 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/33/4313386.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_4313386
loop_
_publ_author_name
'Artur Krężel'
'Rafał Latajka'
'Grzegorz D. Bujacz'
'Wojciech Bal'
_publ_section_title
;
 Coordination Properties of Tris(2-carboxyethyl)phosphine, a Newly
 Introduced Thiol Reductant, and Its Oxide
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1994
_journal_page_last               2003
_journal_paper_doi               10.1021/ic025969y
_journal_volume                  42
_journal_year                    2003
_chemical_formula_sum            'C9 H24 N O10 P Zn'
_chemical_formula_weight         402.63
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           173
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 6c'
_symmetry_space_group_name_H-M   'P 63'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            4
_cell_length_a                   11.528(2)
_cell_length_b                   11.528(2)
_cell_length_c                   15.168(7)
_cell_measurement_temperature    293(2)
_cell_volume                     1745.7(9)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0124
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1435
_diffrn_reflns_theta_max         74.80
_diffrn_reflns_theta_min         4.43
_exptl_absorpt_coefficient_mu    3.256
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_F_000             840
_refine_diff_density_max         0.710
_refine_diff_density_min         -0.670
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.13(10)
_refine_ls_extinction_coef       0.0047(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.120
_refine_ls_goodness_of_fit_obs   1.122
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         1249
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.176
_refine_ls_restrained_S_obs      1.180
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_obs          0.0287
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0510P)²+0.8318P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0816
_refine_ls_wR_factor_obs         0.0814
_reflns_number_observed          1239
_reflns_number_total             1252
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic025969ysi20021119_044203.cif
_cod_data_source_block           bal7pd
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0510P)^2^+0.8318P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0510P)^2^+0.8318P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4313386
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, z+1/2'
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Zn1A Zn 0.3333 0.6667 0.13592(6) 0.0215(2) Uani 1 d S .
P1A P 0.0000 0.0000 0.23164(12) 0.0196(3) Uani 1 d S .
C1A C 0.0895(4) 0.1666(4) 0.1798(3) 0.0333(8) Uani 1 d . .
H11A H 0.1849(4) 0.1986(4) 0.1816(3) 0.044 Uiso 1 calc R .
H12A H 0.0631(4) 0.1582(4) 0.1184(3) 0.044 Uiso 1 calc R .
C2A C 0.0631(5) 0.2699(4) 0.2237(3) 0.0357(9) Uani 1 d . .
H21A H -0.0328(5) 0.2350(4) 0.2271(3) 0.047 Uiso 1 calc R .
H22A H 0.0982(5) 0.2861(4) 0.2833(3) 0.047 Uiso 1 calc R .
C3A C 0.1276(4) 0.4009(3) 0.1730(3) 0.0293(8) Uani 1 d . .
O1A O 0.2457(3) 0.4892(3) 0.1952(2) 0.0366(6) Uani 1 d . .
O2A O 0.0664(3) 0.4158(3) 0.1121(2) 0.0492(8) Uani 1 d . .
Zn1B Zn 0.0000 0.0000 0.38890(6) 0.0220(2) Uani 1 d S .
P1B P 0.6667 0.3333 0.48052(11) 0.0191(3) Uani 1 d S .
C1B C 0.5069(3) 0.2836(4) 0.4292(3) 0.0259(7) Uani 1 d . .
H11B H 0.4776(3) 0.3457(4) 0.4471(3) 0.034 Uiso 1 calc R .
H12B H 0.5189(3) 0.2907(4) 0.3657(3) 0.034 Uiso 1 calc R .
C2B C 0.3978(3) 0.1426(3) 0.4517(3) 0.0290(7) Uani 1 d . .
H21B H 0.4188(3) 0.0788(3) 0.4249(3) 0.039 Uiso 1 calc R .
H22B H 0.3946(3) 0.1301(3) 0.5151(3) 0.039 Uiso 1 calc R .
C3B C 0.2625(3) 0.1158(4) 0.4194(3) 0.0270(7) Uani 1 d . .
O1B O 0.1604(2) 0.0094(3) 0.4482(2) 0.0317(6) Uani 1 d . .
O2B O 0.2536(3) 0.1915(3) 0.3655(3) 0.0448(8) Uani 1 d . .
N1 N 0.2239(16) 0.3839(19) 0.5187(17) 0.059(4) Uani 0.67 d P 1
H11N H 0.1546(16) 0.3069(19) 0.4985(17) 0.078 Uiso 0.67 d PR 1
H12N H 0.2807(16) 0.3646(19) 0.5472(17) 0.078 Uiso 0.67 d PR 1
H13N H 0.1941(16) 0.4243(19) 0.5556(17) 0.078 Uiso 0.67 d PR 1
H14N H 0.2662(16) 0.4397(19) 0.4734(17) 0.078 Uiso 0.67 d PR 1
O1 O 0.1934(40) 0.3687(44) 0.5371(33) 0.097(13) Uani 0.33 d P 2
H11 H 0.1270(40) 0.2950(44) 0.5070(33) 0.129 Uiso 0.33 d PR 2
H12 H 0.2648(40) 0.3628(44) 0.5604(33) 0.129 Uiso 0.33 d PR 2
O2 O 0.4741(17) 0.3589(15) 0.1611(12) 0.182(6) Uani 0.67 d PU 3
H21 H 0.5073(17) 0.4485(15) 0.1469(12) 0.242 Uiso 0.67 d PR 3
H22 H 0.5478(17) 0.3464(15) 0.1591(12) 0.242 Uiso 0.67 d PR 3
O2' O 0.5732(34) 0.3560(36) 0.1478(25) 0.191(13) Uani 0.33 d PU 4
H21' H 0.5295(34) 0.3816(36) 0.1881(25) 0.254 Uiso 0.33 d PR 4
H22' H 0.5055(34) 0.2986(36) 0.1097(25) 0.254 Uiso 0.33 d PR 4
O3 O 0.4224(8) 0.4394(9) 0.2872(8) 0.109(3) Uani 0.67 d PU 5
H31 H 0.3626(8) 0.4561(9) 0.2563(8) 0.146 Uiso 0.67 d PR 5
H32 H 0.3659(8) 0.3570(9) 0.3133(8) 0.146 Uiso 0.67 d PR 5
O4 O 0.3997(20) 0.5916(19) 0.4195(13) 0.099(5) Uani 0.33 d PU 5
H41 H 0.4069(20) 0.5403(19) 0.3748(13) 0.131 Uiso 0.33 d PR 5
H42 H 0.3350(20) 0.5245(19) 0.4549(13) 0.131 Uiso 0.33 d PR 5
O3' O 0.3945(19) 0.5027(23) 0.3521(13) 0.108(6) Uani 0.33 d PU 6
H31' H 0.3358(19) 0.5305(23) 0.3716(13) 0.143 Uiso 0.33 d PR 6
H32' H 0.3527(19) 0.4099(23) 0.3561(13) 0.143 Uiso 0.33 d PR 6
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
_geom_angle_publ_flag
O1A Zn1A O1A 101.09(14) 3_565 2_665 ?
O1A Zn1A O1A 101.09(14) 3_565 . ?
O1A Zn1A O1A 101.09(14) 2_665 . ?
O1A Zn1A P1B 116.93(11) 3_565 4_664 ?
O1A Zn1A P1B 116.93(11) 2_665 4_664 ?
O1A Zn1A P1B 116.93(11) . 4_664 ?
C1A P1A C1A 103.1(2) 2 3 ?
C1A P1A C1A 103.1(2) 2 . ?
C1A P1A C1A 103.1(2) 3 . ?
C1A P1A Zn1B 115.3(2) 2 . ?
C1A P1A Zn1B 115.3(2) 3 . ?
C1A P1A Zn1B 115.3(2) . . ?
C2A C1A P1A 113.8(3) . . ?
C2A C1A H11A 108.8(2) . . ?
P1A C1A H11A 108.81(13) . . ?
C2A C1A H12A 108.8(2) . . ?
P1A C1A H12A 108.8(2) . . ?
H11A C1A H12A 107.7 . . ?
C3A C2A C1A 111.5(3) . . ?
C3A C2A H21A 109.3(2) . . ?
C1A C2A H21A 109.3(2) . . ?
C3A C2A H22A 109.3(2) . . ?
C1A C2A H22A 109.3(2) . . ?
H21A C2A H22A 108.0 . . ?
O2A C3A O1A 123.3(3) . . ?
O2A C3A C2A 119.4(4) . . ?
O1A C3A C2A 117.3(4) . . ?
C3A O1A Zn1A 119.6(3) . . ?
O1B Zn1B O1B 101.50(12) 2 . ?
O1B Zn1B O1B 101.50(12) 2 3 ?
O1B Zn1B O1B 101.50(12) . 3 ?
O1B Zn1B P1A 116.59(10) 2 . ?
O1B Zn1B P1A 116.59(10) . . ?
O1B Zn1B P1A 116.59(10) 3 . ?
C1B P1B C1B 102.8(2) 2_655 3_665 ?
C1B P1B C1B 102.8(2) 2_655 . ?
C1B P1B C1B 102.8(2) 3_665 . ?
C1B P1B Zn1A 115.49(15) 2_655 4_665 ?
C1B P1B Zn1A 115.49(15) 3_665 4_665 ?
C1B P1B Zn1A 115.49(15) . 4_665 ?
C2B C1B P1B 114.2(3) . . ?
C2B C1B H11B 108.7(2) . . ?
P1B C1B H11B 108.70(12) . . ?
C2B C1B H12B 108.7(2) . . ?
P1B C1B H12B 108.70(15) . . ?
H11B C1B H12B 107.6 . . ?
C3B C2B C1B 111.3(3) . . ?
C3B C2B H21B 109.4(2) . . ?
C1B C2B H21B 109.4(2) . . ?
C3B C2B H22B 109.4(2) . . ?
C1B C2B H22B 109.4(2) . . ?
H21B C2B H22B 108.0 . . ?
O2B C3B O1B 122.7(3) . . ?
O2B C3B C2B 120.8(3) . . ?
O1B C3B C2B 116.4(3) . . ?
C3B O1B Zn1B 106.2(2) . . ?
H11N N1 H12N 108.4 . . ?
H11N N1 H13N 110.0 . . ?
H12N N1 H13N 110.0 . . ?
H11N N1 H14N 110.0 . . ?
H12N N1 H14N 110.0 . . ?
H13N N1 H14N 108.4 . . ?
H11 N1 H12 107.0(58) . . ?
H11N O1 H12N 100.2(57) . . ?
H11N O1 H13N 143.5(80) . . ?
H12N O1 H13N 114.6(73) . . ?
H11N O1 H14N 85.3(56) . . ?
H12N O1 H14N 78.4(37) . . ?
H13N O1 H14N 90.7(58) . . ?
H11 O1 H12 118.3 . . ?
H21 O2 H22 105.3 . . ?
H21' O2 H22' 96.6(32) . . ?
H21' O2' H22' 103.8 . . ?
H31 O3 H32 102.3 . . ?
H41 O4 H42 100.5 . . ?
H31' O3' H32' 109.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1A O1A 1.987(3) 3_565 ?
Zn1A O1A 1.987(3) 2_665 ?
Zn1A O1A 1.987(3) . ?
Zn1A P1B 2.357(2) 4_664 ?
P1A C1A 1.841(4) 2 ?
P1A C1A 1.841(4) 3 ?
P1A C1A 1.841(4) . ?
P1A Zn1B 2.385(2) . ?
C1A C2A 1.522(6) . ?
C1A H11A 0.97 . ?
C1A H12A 0.97 . ?
C2A C3A 1.517(5) . ?
C2A H21A 0.97 . ?
C2A H22A 0.97 . ?
C3A O2A 1.226(5) . ?
C3A O1A 1.272(5) . ?
Zn1B O1B 2.011(3) 2 ?
Zn1B O1B 2.011(3) . ?
Zn1B O1B 2.011(3) 3 ?
P1B C1B 1.809(4) 2_655 ?
P1B C1B 1.809(4) 3_665 ?
P1B C1B 1.809(4) . ?
P1B Zn1A 2.357(2) 4_665 ?
C1B C2B 1.515(5) . ?
C1B H11B 0.97 . ?
C1B H12B 0.97 . ?
C2B C3B 1.512(5) . ?
C2B H21B 0.97 . ?
C2B H22B 0.97 . ?
C3B O2B 1.238(5) . ?
C3B O1B 1.279(5) . ?
N1 H11N 0.90 . ?
N1 H12N 0.90 . ?
N1 H13N 0.90 . ?
N1 H14N 0.90 . ?
N1 H11 1.09(6) . ?
N1 H12 0.89(6) . ?
O1 H11 0.93 . ?
O1 H12 0.93 . ?
O2 H21 0.93 . ?
O2 H22 0.93 . ?
O2 H21' 0.69(4) . ?
O2 H22' 1.21(4) . ?
O2' H21' 0.93 . ?
O2' H22' 0.93 . ?
O3 H31 0.93 . ?
O3 H32 0.93 . ?
O3 H32' 1.26(2) . ?
O4 H41 0.93 . ?
O4 H42 0.93 . ?
O4 H31' 1.02(3) . ?
O3' H31' 0.93 . ?
O3' H32' 0.93 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1A P1A C1A C2A 83.9(5) 2 . . . ?
C1A P1A C1A C2A -169.1(3) 3 . . . ?
Zn1B P1A C1A C2A -42.6(4) . . . . ?
P1A C1A C2A C3A -174.2(3) . . . . ?
C1A C2A C3A O2A 86.7(5) . . . . ?
C1A C2A C3A O1A -91.4(5) . . . . ?
O2A C3A O1A Zn1A 4.9(5) . . . . ?
C2A C3A O1A Zn1A -177.0(3) . . . . ?
O1A Zn1A O1A C3A 77.2(4) 3_565 . . . ?
O1A Zn1A O1A C3A -179.0(3) 2_665 . . . ?
P1B Zn1A O1A C3A -50.9(3) 4_664 . . . ?
C1A P1A Zn1B O1B -84.6(2) 2 . . 2 ?
C1A P1A Zn1B O1B 155.4(2) 3 . . 2 ?
C1A P1A Zn1B O1B 35.4(2) . . . 2 ?
C1A P1A Zn1B O1B 155.4(2) 2 . . . ?
C1A P1A Zn1B O1B 35.4(2) 3 . . . ?
C1A P1A Zn1B O1B -84.6(2) . . . . ?
C1A P1A Zn1B O1B 35.4(2) 2 . . 3 ?
C1A P1A Zn1B O1B -84.6(2) 3 . . 3 ?
C1A P1A Zn1B O1B 155.4(2) . . . 3 ?
C1B P1B C1B C2B 65.9(4) 2_655 . . . ?
C1B P1B C1B C2B 172.5(2) 3_665 . . . ?
Zn1A P1B C1B C2B -60.8(3) 4_665 . . . ?
P1B C1B C2B C3B 170.5(3) . . . . ?
C1B C2B C3B O2B 14.6(5) . . . . ?
C1B C2B C3B O1B -167.9(3) . . . . ?
O2B C3B O1B Zn1B 0.0(4) . . . . ?
C2B C3B O1B Zn1B -177.5(3) . . . . ?
O1B Zn1B O1B C3B -70.7(3) 2 . . . ?
O1B Zn1B O1B C3B -175.1(2) 3 . . . ?
P1A Zn1B O1B C3B 57.1(2) . . . . ?
