#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:31:45 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179451 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/48/4334837.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_4334837
loop_
_publ_author_name
'Rui Li'
'Yanxia Zhao'
'Shaoguang Li'
'Peiju Yang'
'Xiaojuan Huang'
'Xiao-Juan Yang'
'Biao Wu'
_publ_contact_author_address
; Lanzhou Institute of Chemical Physics, 
Chinese Academy of Sciences, Lanzhou 730000, P. R. China
;
_publ_contact_author_email       yangxj@lzb.ac.cn
_publ_contact_author_fax         +86-931-4968286
_publ_contact_author_name        'Xiao-Juan, Yang'
_publ_contact_author_phone       +86-931-4968286
_publ_section_title
;
 Tris Chelating Phosphate Complexes of Bis(thio)urea Ligands
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5851
_journal_page_last               5860
_journal_paper_doi               10.1021/ic3028012
_journal_volume                  52
_journal_year                    2013
_chemical_formula_sum            'C41 H76 N10 O7'
_chemical_formula_weight         821.12
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.893(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.123(2)
_cell_length_b                   20.426(5)
_cell_length_c                   13.377(4)
_cell_measurement_temperature    153(2)
_cell_volume                     2372.2(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scan'
_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  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15911
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9804
_exptl_absorpt_correction_T_min  0.9766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4277
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.1324
_refine_ls_R_factor_gt           0.0924
_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)+(0.0000P)²+2.8371P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1540
_refine_ls_wR_factor_ref         0.1711
_reflns_number_gt                2515
_reflns_number_total             4277
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic3028012_si_002_7.cif
_cod_data_source_block           4
_cod_original_cell_volume        2372.1(11)
_cod_database_code               4334837
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.7899(4) 0.16176(16) 0.2827(2) 0.1076(11) Uani 1 1 d .
O2 O 0.9666(7) 0.1360(2) 0.7837(4) 0.249(3) Uani 1 1 d .
O3 O 0.5854(7) 0.0401(3) 0.5053(6) 0.174(3) Uani 0.75 1 d P
O4 O 0.5335(6) -0.0048(4) 0.6078(5) 0.195(3) Uani 0.75 1 d P
N1 N 0.6486(4) 0.07048(18) 0.2786(3) 0.1008(12) Uani 1 1 d .
H1 H 0.5823 0.0502 0.3037 0.121 Uiso 1 1 calc R
N2 N 0.6734(3) 0.14373(15) 0.4084(2) 0.0765(10) Uani 1 1 d .
H2 H 0.6069 0.1188 0.4263 0.092 Uiso 1 1 calc R
N3 N 0.7955(4) 0.12695(16) 0.6241(2) 0.0820(10) Uani 1 1 d .
H3 H 0.7416 0.0975 0.5800 0.098 Uiso 1 1 calc R
N4 N 0.8089(5) 0.0497(2) 0.7442(3) 0.1321(17) Uani 1 1 d .
H4 H 0.7401 0.0288 0.6935 0.158 Uiso 1 1 calc R
N5 N 0.2688(3) 0.18631(16) 0.5284(3) 0.0812(10) Uani 1 1 d .
C1 C 0.5928(19) 0.0001(7) 0.1308(10) 0.465(12) Uani 1 1 d D
H1A H 0.5343 0.0221 0.0657 0.697 Uiso 1 1 calc R
H1B H 0.5219 -0.0154 0.1679 0.697 Uiso 1 1 calc R
H1C H 0.6484 -0.0373 0.1141 0.697 Uiso 1 1 calc R
C2 C 0.6921(11) 0.0415(4) 0.1911(6) 0.212(4) Uani 1 1 d D
H2A H 0.7091 0.0775 0.1463 0.254 Uiso 1 1 calc R
H2B H 0.7916 0.0185 0.2205 0.254 Uiso 1 1 calc R
C3 C 0.7099(4) 0.1278(2) 0.3203(3) 0.0772(11) Uani 1 1 d .
C4 C 0.7363(4) 0.19802(19) 0.4727(3) 0.0695(10) Uani 1 1 d .
C5 C 0.7339(5) 0.2598(2) 0.4299(3) 0.0866(12) Uani 1 1 d .
H5 H 0.6867 0.2659 0.3566 0.104 Uiso 1 1 calc R
C6 C 0.7987(6) 0.3126(2) 0.4914(4) 0.1026(15) Uani 1 1 d .
H6 H 0.7978 0.3546 0.4609 0.123 Uiso 1 1 calc R
C7 C 0.8644(5) 0.3038(2) 0.5973(4) 0.1015(15) Uani 1 1 d .
H7 H 0.9105 0.3400 0.6400 0.122 Uiso 1 1 calc R
C8 C 0.8650(4) 0.2430(2) 0.6434(3) 0.0839(12) Uani 1 1 d .
H8 H 0.9097 0.2380 0.7171 0.101 Uiso 1 1 calc R
C9 C 0.8007(4) 0.18977(18) 0.5822(3) 0.0692(10) Uani 1 1 d .
C10 C 0.8623(6) 0.1064(3) 0.7225(4) 0.1232(19) Uani 1 1 d .
C11 C 0.8595(10) 0.0204(4) 0.8488(5) 0.213(4) Uani 1 1 d U
H11A H 0.9732 0.0238 0.8750 0.256 Uiso 1 1 calc R
H11B H 0.8189 0.0479 0.8952 0.256 Uiso 1 1 calc R
C12 C 0.8252(11) -0.0376(4) 0.8612(6) 0.250(5) Uani 1 1 d .
H12A H 0.7132 -0.0431 0.8336 0.376 Uiso 1 1 calc R
H12B H 0.8601 -0.0484 0.9363 0.376 Uiso 1 1 calc R
H12C H 0.8753 -0.0668 0.8236 0.376 Uiso 1 1 calc R
C13 C 0.5000 0.0000 0.5000 0.0860(17) Uani 1 2 d S
C14 C 0.4042(5) 0.1619(2) 0.6172(4) 0.1087(15) Uani 1 1 d .
H14A H 0.4208 0.1151 0.6049 0.130 Uiso 1 1 calc R
H14B H 0.4974 0.1861 0.6155 0.130 Uiso 1 1 calc R
C15 C 0.3867(7) 0.1690(3) 0.7252(4) 0.143(2) Uani 1 1 d .
H15A H 0.3744 0.2154 0.7397 0.215 Uiso 1 1 calc R
H15B H 0.4786 0.1516 0.7777 0.215 Uiso 1 1 calc R
H15C H 0.2958 0.1446 0.7285 0.215 Uiso 1 1 calc R
C16 C 0.1223(5) 0.1513(2) 0.5280(4) 0.0996(14) Uani 1 1 d .
H16A H 0.1042 0.1595 0.5962 0.119 Uiso 1 1 calc R
H16B H 0.0353 0.1710 0.4726 0.119 Uiso 1 1 calc R
C17 C 0.1199(6) 0.0792(3) 0.5104(4) 0.135(2) Uani 1 1 d .
H17A H 0.1358 0.0702 0.4426 0.202 Uiso 1 1 calc R
H17B H 0.0200 0.0615 0.5105 0.202 Uiso 1 1 calc R
H17C H 0.2021 0.0586 0.5667 0.202 Uiso 1 1 calc R
C18 C 0.3053(5) 0.1738(2) 0.4271(4) 0.1031(15) Uani 1 1 d .
H18A H 0.4021 0.1968 0.4305 0.124 Uiso 1 1 calc R
H18B H 0.3237 0.1263 0.4219 0.124 Uiso 1 1 calc R
C19 C 0.1829(6) 0.1949(3) 0.3290(4) 0.141(2) Uani 1 1 d .
H19A H 0.0885 0.1698 0.3215 0.211 Uiso 1 1 calc R
H19B H 0.2184 0.1870 0.2680 0.211 Uiso 1 1 calc R
H19C H 0.1618 0.2417 0.3336 0.211 Uiso 1 1 calc R
C20 C 0.2430(6) 0.2586(2) 0.5421(4) 0.1141(17) Uani 1 1 d .
H20A H 0.2212 0.2647 0.6096 0.137 Uiso 1 1 calc R
H20B H 0.1504 0.2726 0.4852 0.137 Uiso 1 1 calc R
C21 C 0.3775(8) 0.3035(3) 0.5413(5) 0.151(2) Uani 1 1 d .
H21A H 0.4740 0.2851 0.5869 0.226 Uiso 1 1 calc R
H21B H 0.3613 0.3470 0.5669 0.226 Uiso 1 1 calc R
H21C H 0.3829 0.3071 0.4694 0.226 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'
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 O3 C13 0.0(9) 1 .
O3 O3 O4 0(10) 1 3_656
C13 O3 O4 53.1(3) . 3_656
O4 O4 C13 0.0(5) 1 .
O4 O4 O3 0(10) 1 3_656
C13 O4 O3 40.3(3) . 3_656
C3 N1 C2 120.1(4) . .
C3 N1 H1 119.9 . .
C2 N1 H1 119.9 . .
C3 N2 C4 123.7(3) . .
C3 N2 H2 118.2 . .
C4 N2 H2 118.2 . .
C10 N3 C9 128.2(4) . .
C10 N3 H3 115.9 . .
C9 N3 H3 115.9 . .
C10 N4 C11 122.7(5) . .
C10 N4 H4 118.7 . .
C11 N4 H4 118.7 . .
C14 N5 C18 107.2(3) . .
C14 N5 C16 110.8(3) . .
C18 N5 C16 110.7(3) . .
C14 N5 C20 110.2(4) . .
C18 N5 C20 111.0(3) . .
C16 N5 C20 106.9(3) . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C1 C2 N1 116.3(8) . .
C1 C2 H2A 108.2 . .
N1 C2 H2A 108.2 . .
C1 C2 H2B 108.2 . .
N1 C2 H2B 108.2 . .
H2A C2 H2B 107.4 . .
O1 C3 N1 123.3(4) . .
O1 C3 N2 124.0(4) . .
N1 C3 N2 112.8(4) . .
C5 C4 C9 119.2(4) . .
C5 C4 N2 120.8(3) . .
C9 C4 N2 120.0(3) . .
C6 C5 C4 121.2(4) . .
C6 C5 H5 119.4 . .
C4 C5 H5 119.4 . .
C7 C6 C5 119.1(4) . .
C7 C6 H6 120.4 . .
C5 C6 H6 120.4 . .
C6 C7 C8 121.2(4) . .
C6 C7 H7 119.4 . .
C8 C7 H7 119.4 . .
C9 C8 C7 120.0(4) . .
C9 C8 H8 120.0 . .
C7 C8 H8 120.0 . .
C8 C9 N3 122.9(4) . .
C8 C9 C4 119.2(4) . .
N3 C9 C4 118.0(3) . .
O2 C10 N4 123.8(5) . .
O2 C10 N3 122.3(5) . .
N4 C10 N3 113.8(4) . .
C12 C11 N4 119.9(7) . .
C12 C11 H11A 107.4 . .
N4 C11 H11A 107.4 . .
C12 C11 H11B 107.4 . .
N4 C11 H11B 107.4 . .
H11A C11 H11B 106.9 . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
O3 C13 O3 0.0(8) 1 .
O3 C13 O3 179.997(1) 1 3_656
O3 C13 O3 179.997(1) . 3_656
O3 C13 O4 86.6(4) 1 3_656
O3 C13 O4 86.6(4) . 3_656
O3 C13 O4 93.4(4) 3_656 3_656
O3 C13 O4 93.4(4) 1 1
O3 C13 O4 93.4(4) . 1
O3 C13 O4 86.6(4) 3_656 1
O4 C13 O4 180.000(1) 3_656 1
O3 C13 O4 93.4(4) 1 .
O3 C13 O4 93.4(4) . .
O3 C13 O4 86.6(4) 3_656 .
O4 C13 O4 180.000(1) 3_656 .
O4 C13 O4 0.0(8) 1 .
C15 C14 N5 114.8(4) . .
C15 C14 H14A 108.6 . .
N5 C14 H14A 108.6 . .
C15 C14 H14B 108.6 . .
N5 C14 H14B 108.6 . .
H14A C14 H14B 107.5 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C17 C16 N5 116.0(4) . .
C17 C16 H16A 108.3 . .
N5 C16 H16A 108.3 . .
C17 C16 H16B 108.3 . .
N5 C16 H16B 108.3 . .
H16A C16 H16B 107.4 . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C19 C18 N5 115.1(4) . .
C19 C18 H18A 108.5 . .
N5 C18 H18A 108.5 . .
C19 C18 H18B 108.5 . .
N5 C18 H18B 108.5 . .
H18A C18 H18B 107.5 . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
N5 C20 C21 115.3(4) . .
N5 C20 H20A 108.4 . .
C21 C20 H20A 108.4 . .
N5 C20 H20B 108.4 . .
C21 C20 H20B 108.4 . .
H20A C20 H20B 107.5 . .
C20 C21 H21A 109.5 . .
C20 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C20 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C3 1.221(4) .
O2 C10 1.210(5) .
O3 O3 0.000(10) 1
O3 C13 1.118(5) .
O3 O4 1.726(8) 3_656
O4 O4 0.00(2) 1
O4 C13 1.383(7) .
O4 O3 1.726(8) 3_656
N1 C3 1.343(5) .
N1 C2 1.471(6) .
N1 H1 0.8800 .
N2 C3 1.358(4) .
N2 C4 1.413(4) .
N2 H2 0.8800 .
N3 C10 1.337(5) .
N3 C9 1.407(4) .
N3 H3 0.8800 .
N4 C10 1.322(6) .
N4 C11 1.461(7) .
N4 H4 0.8800 .
N5 C14 1.511(5) .
N5 C18 1.513(5) .
N5 C16 1.514(5) .
N5 C20 1.515(5) .
C1 C2 1.317(9) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C4 C5 1.383(5) .
C4 C9 1.410(5) .
C5 C6 1.374(6) .
C5 H5 0.9500 .
C6 C7 1.370(6) .
C6 H6 0.9500 .
C7 C8 1.385(6) .
C7 H7 0.9500 .
C8 C9 1.379(5) .
C8 H8 0.9500 .
C11 C12 1.250(8) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 O3 1.118(5) 1
C13 O3 1.118(5) 3_656
C13 O4 1.383(7) 3_656
C13 O4 1.383(7) 1
C14 C15 1.509(6) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 C17 1.490(6) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 C19 1.502(6) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 C21 1.534(7) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
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
N1 H1 O4 0.88 2.04 2.901(7) 167.4 3_656
N4 H4 O4 0.88 2.00 2.839(7) 158.5 1
N3 H3 O3 0.88 1.88 2.734(6) 163.8 1
N2 H2 O3 0.88 1.97 2.728(6) 144.2 1
