#------------------------------------------------------------------------------
#$Date: 2023-12-22 17:07:40 +0200 (Fri, 22 Dec 2023) $
#$Revision: 288505 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/33/41/4334169.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_4334169
loop_
_publ_author_name
'Daniel Rosario-Amorin'
'Sabrina Ouizem'
'Diane A. Dickie'
'Yufeng Wen'
'Robert T. Paine'
'Jian Gao'
'John K. Grey'
'Ana de Bettencourt-Dias'
'Benjamin P. Hay'
'Laetitia H. Delmau'
_publ_section_title
;
 Synthesis, Lanthanide Coordination Chemistry, and Liquid-Liquid
 Extraction Performance of CMPO-Decorated Pyridine and Pyridine N-Oxide
 Platforms
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3063
_journal_page_last               3083
_journal_paper_doi               10.1021/ic3025342
_journal_volume                  52
_journal_year                    2013
_chemical_formula_sum            'C41 H45 N3 O5 P2'
_chemical_formula_weight         721.74
_space_group_IT_number           41
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'A 2 -2ab'
_symmetry_space_group_name_H-M   'A e a 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.2568(18)
_cell_length_b                   15.4841(13)
_cell_length_c                   10.8479(8)
_cell_measurement_reflns_used    9907
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.94
_cell_measurement_theta_min      2.63
_cell_volume                     3738.5(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            30689
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_T_max  0.9698
_exptl_absorpt_correction_T_min  0.9251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1528
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         4296
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0411P)²+1.1074P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0726
_refine_ls_wR_factor_ref         0.0757
_reflns_number_gt                3924
_reflns_number_total             4296
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic3025342_si_001_04.cif
_cod_data_source_block           aba2_Ligand_9S,S
_cod_depositor_comments
;

2021-11-23
Space group name changed to comply with IUCR recomendations
                 miguel

The following automatic conversions were performed:

data name '_iucr_refine_instruction_details' was replaced with
'_iucr_refine_instructions_details' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_sg_symbol_H-M      'A b a 2'
_cod_database_code               4334169
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/2, y+1, z+1/2'
'x+1/2, -y+1, 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
P1 P 0.605320(14) 0.30573(2) 0.51578(4) 0.02415(9) Uani 1 1 d .
O1 O 0.5000 0.5000 0.36899(13) 0.0286(3) Uani 1 2 d S
O2 O 0.63361(5) 0.29028(8) 0.63732(10) 0.0337(3) Uani 1 1 d .
O3 O 0.67385(6) 0.48622(9) 0.59546(12) 0.0423(3) Uani 1 1 d .
N1 N 0.5000 0.5000 0.49067(16) 0.0258(4) Uani 1 2 d S
N2 N 0.68622(6) 0.49239(9) 0.38954(14) 0.0322(3) Uani 1 1 d .
C1 C 0.54691(7) 0.46162(10) 0.55337(14) 0.0263(3) Uani 1 1 d .
C2 C 0.54662(8) 0.46171(12) 0.68100(15) 0.0364(4) Uani 1 1 d .
H2 H 0.5787 0.4353 0.7248 0.044 Uiso 1 1 calc R
C3 C 0.5000 0.5000 0.7453(2) 0.0418(6) Uani 1 2 d S
H3 H 0.5000 0.5000 0.8329 0.050 Uiso 1 2 calc SR
C4 C 0.59530(6) 0.42128(10) 0.47575(14) 0.0242(3) Uani 1 1 d .
H4 H 0.5830 0.4252 0.3873 0.029 Uiso 1 1 calc R
C5 C 0.65567(7) 0.46973(10) 0.49159(15) 0.0279(3) Uani 1 1 d .
C6 C 0.66853(8) 0.47546(11) 0.26126(16) 0.0338(4) Uani 1 1 d .
H6A H 0.6454 0.4209 0.2577 0.041 Uiso 1 1 calc R
H6B H 0.7051 0.4681 0.2103 0.041 Uiso 1 1 calc R
C7 C 0.63073(9) 0.54810(13) 0.20804(19) 0.0433(4) Uani 1 1 d .
H7A H 0.5926 0.5518 0.2530 0.065 Uiso 1 1 calc R
H7B H 0.6227 0.5365 0.1208 0.065 Uiso 1 1 calc R
H7C H 0.6525 0.6028 0.2160 0.065 Uiso 1 1 calc R
C8 C 0.74270(8) 0.54144(12) 0.4053(2) 0.0459(5) Uani 1 1 d .
H8A H 0.7410 0.5734 0.4843 0.055 Uiso 1 1 calc R
H8B H 0.7461 0.5844 0.3381 0.055 Uiso 1 1 calc R
C9 C 0.79791(8) 0.48500(15) 0.40462(19) 0.0479(5) Uani 1 1 d .
H9A H 0.7958 0.4439 0.4732 0.072 Uiso 1 1 calc R
H9B H 0.8338 0.5211 0.4136 0.072 Uiso 1 1 calc R
H9C H 0.8000 0.4533 0.3266 0.072 Uiso 1 1 calc R
C10 C 0.64928(7) 0.26515(10) 0.38895(16) 0.0299(3) Uani 1 1 d .
C11 C 0.71079(7) 0.28538(11) 0.38901(19) 0.0374(4) Uani 1 1 d .
H11 H 0.7280 0.3141 0.4579 0.045 Uiso 1 1 calc R
C12 C 0.74644(10) 0.26363(13) 0.2890(2) 0.0502(5) Uani 1 1 d .
H12 H 0.7877 0.2793 0.2878 0.060 Uiso 1 1 calc R
C13 C 0.72212(11) 0.21981(14) 0.1927(2) 0.0557(6) Uani 1 1 d .
H13 H 0.7468 0.2052 0.1243 0.067 Uiso 1 1 calc R
C14 C 0.66204(12) 0.19594(14) 0.1919(2) 0.0571(6) Uani 1 1 d .
H14 H 0.6461 0.1636 0.1251 0.069 Uiso 1 1 calc R
C15 C 0.62500(9) 0.22000(12) 0.29096(19) 0.0429(4) Uani 1 1 d .
H15 H 0.5836 0.2053 0.2906 0.051 Uiso 1 1 calc R
C16 C 0.53161(6) 0.25797(10) 0.50336(15) 0.0278(3) Uani 1 1 d .
C17 C 0.48799(7) 0.28329(12) 0.41834(17) 0.0374(4) Uani 1 1 d .
H17 H 0.4950 0.3315 0.3661 0.045 Uiso 1 1 calc R
C18 C 0.43439(8) 0.23792(15) 0.4102(2) 0.0503(5) Uani 1 1 d .
H18 H 0.4048 0.2547 0.3519 0.060 Uiso 1 1 calc R
C19 C 0.42409(9) 0.16817(15) 0.4871(2) 0.0545(5) Uani 1 1 d .
H19 H 0.3874 0.1371 0.4807 0.065 Uiso 1 1 calc R
C20 C 0.46620(10) 0.14336(14) 0.5726(2) 0.0499(5) Uani 1 1 d .
H20 H 0.4585 0.0958 0.6256 0.060 Uiso 1 1 calc R
C21 C 0.52041(9) 0.18829(11) 0.58115(17) 0.0373(4) Uani 1 1 d .
H21 H 0.5497 0.1713 0.6401 0.045 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'
P P 0.1023 0.0942 '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 P1 C10 113.13(7) . .
O2 P1 C16 112.76(7) . .
C10 P1 C16 107.09(8) . .
O2 P1 C4 114.56(7) . .
C10 P1 C4 102.88(7) . .
C16 P1 C4 105.58(7) . .
O1 N1 C1 119.52(9) . .
O1 N1 C1 119.52(9) . 2_665
C1 N1 C1 120.96(18) . 2_665
C5 N2 C6 126.65(14) . .
C5 N2 C8 117.94(15) . .
C6 N2 C8 115.39(14) . .
N1 C1 C2 119.26(14) . .
N1 C1 C4 116.41(13) . .
C2 C1 C4 124.32(14) . .
C3 C2 C1 120.53(16) . .
C3 C2 H2 119.7 . .
C1 C2 H2 119.7 . .
C2 C3 C2 119.5(2) 2_665 .
C2 C3 H3 120.3 2_665 .
C2 C3 H3 120.3 . .
C1 C4 C5 111.00(12) . .
C1 C4 P1 110.85(10) . .
C5 C4 P1 109.70(9) . .
C1 C4 H4 108.4 . .
C5 C4 H4 108.4 . .
P1 C4 H4 108.4 . .
O3 C5 N2 122.40(14) . .
O3 C5 C4 119.34(14) . .
N2 C5 C4 118.26(14) . .
N2 C6 C7 112.10(15) . .
N2 C6 H6A 109.2 . .
C7 C6 H6A 109.2 . .
N2 C6 H6B 109.2 . .
C7 C6 H6B 109.2 . .
H6A C6 H6B 107.9 . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
N2 C8 C9 113.24(15) . .
N2 C8 H8A 108.9 . .
C9 C8 H8A 108.9 . .
N2 C8 H8B 108.9 . .
C9 C8 H8B 108.9 . .
H8A C8 H8B 107.7 . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C15 C10 C11 119.62(17) . .
C15 C10 P1 123.47(13) . .
C11 C10 P1 116.83(14) . .
C12 C11 C10 120.2(2) . .
C12 C11 H11 119.9 . .
C10 C11 H11 119.9 . .
C13 C12 C11 119.7(2) . .
C13 C12 H12 120.2 . .
C11 C12 H12 120.2 . .
C12 C13 C14 121.45(19) . .
C12 C13 H13 119.3 . .
C14 C13 H13 119.3 . .
C13 C14 C15 119.4(2) . .
C13 C14 H14 120.3 . .
C15 C14 H14 120.3 . .
C10 C15 C14 119.54(19) . .
C10 C15 H15 120.2 . .
C14 C15 H15 120.2 . .
C21 C16 C17 119.59(15) . .
C21 C16 P1 115.78(12) . .
C17 C16 P1 124.53(13) . .
C18 C17 C16 119.88(18) . .
C18 C17 H17 120.1 . .
C16 C17 H17 120.1 . .
C19 C18 C17 119.96(19) . .
C19 C18 H18 120.0 . .
C17 C18 H18 120.0 . .
C20 C19 C18 120.81(17) . .
C20 C19 H19 119.6 . .
C18 C19 H19 119.6 . .
C19 C20 C21 119.71(18) . .
C19 C20 H20 120.1 . .
C21 C20 H20 120.1 . .
C16 C21 C20 120.03(17) . .
C16 C21 H21 120.0 . .
C20 C21 H21 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 O2 1.4805(12) .
P1 C10 1.8013(17) .
P1 C16 1.8046(15) .
P1 C4 1.8547(15) .
O1 N1 1.320(2) .
O3 C5 1.224(2) .
N1 C1 1.3804(17) .
N1 C1 1.3804(17) 2_665
N2 C5 1.346(2) .
N2 C6 1.470(2) .
N2 C8 1.479(2) .
C1 C2 1.385(2) .
C1 C4 1.503(2) .
C2 C3 1.384(2) .
C2 H2 0.9500 .
C3 C2 1.384(2) 2_665
C3 H3 0.9500 .
C4 C5 1.548(2) .
C4 H4 1.0000 .
C6 C7 1.519(2) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 C9 1.508(3) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 C15 1.382(3) .
C10 C11 1.404(2) .
C11 C12 1.386(3) .
C11 H11 0.9500 .
C12 C13 1.358(3) .
C12 H12 0.9500 .
C13 C14 1.387(4) .
C13 H13 0.9500 .
C14 C15 1.404(3) .
C14 H14 0.9500 .
C15 H15 0.9500 .
C16 C21 1.392(2) .
C16 C17 1.395(2) .
C17 C18 1.387(2) .
C17 H17 0.9500 .
C18 C19 1.384(3) .
C18 H18 0.9500 .
C19 C20 1.373(3) .
C19 H19 0.9500 .
C20 C21 1.396(3) .
C20 H20 0.9500 .
C21 H21 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
O1 N1 C1 C2 -179.91(12) . .
C1 N1 C1 C2 0.09(12) 2_665 .
O1 N1 C1 C4 -0.43(15) . .
C1 N1 C1 C4 179.57(15) 2_665 .
N1 C1 C2 C3 -0.2(2) . .
C4 C1 C2 C3 -179.62(13) . .
C1 C2 C3 C2 0.09(13) . 2_665
N1 C1 C4 C5 114.22(14) . .
C2 C1 C4 C5 -66.3(2) . .
N1 C1 C4 P1 -123.61(11) . .
C2 C1 C4 P1 55.8(2) . .
O2 P1 C4 C1 -71.13(12) . .
C10 P1 C4 C1 165.67(11) . .
C16 P1 C4 C1 53.54(12) . .
O2 P1 C4 C5 51.80(12) . .
C10 P1 C4 C5 -71.40(12) . .
C16 P1 C4 C5 176.47(11) . .
C6 N2 C5 O3 179.75(16) . .
C8 N2 C5 O3 -2.0(2) . .
C6 N2 C5 C4 -0.4(2) . .
C8 N2 C5 C4 177.80(13) . .
C1 C4 C5 O3 48.33(19) . .
P1 C4 C5 O3 -74.51(16) . .
C1 C4 C5 N2 -131.50(14) . .
P1 C4 C5 N2 105.66(14) . .
C5 N2 C6 C7 90.11(19) . .
C8 N2 C6 C7 -88.15(18) . .
C5 N2 C8 C9 95.6(2) . .
C6 N2 C8 C9 -85.94(19) . .
O2 P1 C10 C15 136.09(15) . .
C16 P1 C10 C15 11.24(17) . .
C4 P1 C10 C15 -99.76(15) . .
O2 P1 C10 C11 -47.33(14) . .
C16 P1 C10 C11 -172.18(12) . .
C4 P1 C10 C11 76.81(13) . .
C15 C10 C11 C12 2.9(2) . .
P1 C10 C11 C12 -173.84(13) . .
C10 C11 C12 C13 -2.4(3) . .
C11 C12 C13 C14 -0.1(3) . .
C12 C13 C14 C15 2.1(3) . .
C11 C10 C15 C14 -0.8(3) . .
P1 C10 C15 C14 175.64(14) . .
C13 C14 C15 C10 -1.6(3) . .
O2 P1 C16 C21 -24.22(15) . .
C10 P1 C16 C21 100.85(14) . .
C4 P1 C16 C21 -150.01(13) . .
O2 P1 C16 C17 159.30(14) . .
C10 P1 C16 C17 -75.63(16) . .
C4 P1 C16 C17 33.51(16) . .
C21 C16 C17 C18 -1.3(3) . .
P1 C16 C17 C18 175.07(15) . .
C16 C17 C18 C19 0.6(3) . .
C17 C18 C19 C20 0.5(3) . .
C18 C19 C20 C21 -0.8(3) . .
C17 C16 C21 C20 1.0(3) . .
P1 C16 C21 C20 -175.69(14) . .
C19 C20 C21 C16 0.1(3) . .
