#------------------------------------------------------------------------------
#$Date: 2020-10-06 02:25:31 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257185 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/88/4038870.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_4038870
loop_
_publ_author_name
'Musina, Elvira I.'
'Wittmann, Tatiana I.'
'Musin, Lenar'
'Balueva, Anna S.'
'Shpagina, Alena S.'
'Litvinov, Igor A.'
'Lönnecke, Peter'
'Hey-Hawkins, Evamarie'
'Karasik, Andrey A.'
'Sinyashin, Oleg G.'
_publ_section_title
;
 Dynamic covalent chemistry approach toward 18-membered
 P₄N₂ macrocycles and their nickel(II) complexes.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01317
_journal_year                    2020
_chemical_formula_moiety         'C48 H58 N6 O4 P4 [+ solvent]'
_chemical_formula_sum            'C24 H29 N3 O2 P2'
_chemical_formula_weight         453.44
_chemical_melting_point          486
_chemical_name_systematic
;
1,10-Di(4?-methylbenzyl)-3,8,12,17-(RSSR)-tetra(pyridine-2?-yl)-3,8,12,17-
tetraoxo-1,10-diaza?3,8,12,17?tetraphosphacyclooctadecane
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                113.230(16)
_cell_angle_beta                 104.32(2)
_cell_angle_gamma                98.18(2)
_cell_formula_units_Z            2
_cell_length_a                   10.11(3)
_cell_length_b                   11.896(16)
_cell_length_c                   12.699(17)
_cell_measurement_reflns_used    637
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      16.56
_cell_measurement_theta_min      2.86
_cell_volume                     1310(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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1789
_diffrn_reflns_av_unetI/netI     0.2882
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13809
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         1.934
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.5752
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_description       formless
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.891
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         5120
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.891
_refine_ls_R_factor_all          0.2882
_refine_ls_R_factor_gt           0.0788
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0931P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1697
_refine_ls_wR_factor_ref         0.2549
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1336
_reflns_number_total             5120
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01317_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4038870
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2471(7) 0.7017(7) 0.3875(6) 0.079(2) Uani 1 1 d . . . . .
H1A H 0.295570 0.756367 0.473508 0.095 Uiso 1 1 calc R U . . .
H1B H 0.220346 0.615244 0.376750 0.095 Uiso 1 1 calc R U . . .
C2 C 0.4376(7) 0.6249(6) 0.3250(6) 0.073(2) Uani 1 1 d . . . . .
H2A H 0.463598 0.627359 0.404892 0.087 Uiso 1 1 calc R U . . .
H2B H 0.523944 0.656859 0.313514 0.087 Uiso 1 1 calc R U . . .
C3 C 0.3440(9) 0.4545(8) 0.0685(6) 0.103(3) Uani 1 1 d . . . . .
H3A H 0.417844 0.523337 0.078506 0.124 Uiso 1 1 calc R U . . .
H3B H 0.362869 0.375619 0.021126 0.124 Uiso 1 1 calc R U . . .
C4 C 0.2102(10) 0.4593(9) -0.0017(8) 0.136(4) Uani 1 1 d . . . . .
H4A H 0.220643 0.544574 0.005534 0.163 Uiso 1 1 calc R U . . .
H4B H 0.140016 0.444565 0.034834 0.163 Uiso 1 1 calc R U . . .
C5 C -0.1527(9) 0.6336(7) 0.1359(6) 0.097(3) Uani 1 1 d . . . . .
H5A H -0.147197 0.719360 0.145518 0.117 Uiso 1 1 calc R U . . .
H5B H -0.216291 0.614450 0.176223 0.117 Uiso 1 1 calc R U . . .
C6 C -0.0070(8) 0.6246(7) 0.1934(6) 0.087(2) Uani 1 1 d . . . . .
H6A H 0.048210 0.623377 0.140585 0.104 Uiso 1 1 calc R U . . .
H6B H -0.017168 0.544430 0.197842 0.104 Uiso 1 1 calc R U . . .
C7 C 0.4278(8) 0.8409(7) 0.3705(7) 0.086(2) Uani 1 1 d . . . . .
H7A H 0.495162 0.865091 0.449973 0.104 Uiso 1 1 calc R U . . .
H7B H 0.364370 0.895337 0.381264 0.104 Uiso 1 1 calc R U . . .
C8 C 0.5062(10) 0.8637(7) 0.2929(8) 0.077(2) Uani 1 1 d . . . . .
C9 C 0.6491(9) 0.9232(7) 0.3363(8) 0.084(2) Uani 1 1 d . . . . .
H9 H 0.701302 0.949216 0.417198 0.101 Uiso 1 1 calc R U . . .
C10 C 0.7151(8) 0.9444(7) 0.2602(9) 0.087(2) Uani 1 1 d . . . . .
H10 H 0.812194 0.982263 0.290776 0.104 Uiso 1 1 calc R U . . .
C11 C 0.6424(12) 0.9115(8) 0.1412(10) 0.093(3) Uani 1 1 d . . . . .
C12 C 0.5015(12) 0.8523(8) 0.0981(8) 0.096(3) Uani 1 1 d . . . . .
H12 H 0.450384 0.826710 0.016986 0.116 Uiso 1 1 calc R U . . .
C13 C 0.4322(9) 0.8291(7) 0.1718(9) 0.095(3) Uani 1 1 d . . . . .
H13 H 0.335329 0.790101 0.140212 0.114 Uiso 1 1 calc R U . . .
C14 C 0.7186(10) 0.9418(8) 0.0634(8) 0.134(4) Uani 1 1 d . . . . .
H14A H 0.816808 0.983401 0.110546 0.201 Uiso 1 1 calc R U . . .
H14B H 0.710663 0.864596 -0.005113 0.201 Uiso 1 1 calc R U . . .
H14C H 0.676798 0.996798 0.035303 0.201 Uiso 1 1 calc R U . . .
C15 C 0.4954(11) 0.3852(10) 0.2401(6) 0.080(2) Uani 1 1 d . . . . .
C16 C 0.4634(10) 0.2815(10) 0.2617(7) 0.098(3) Uani 1 1 d . . . . .
H16 H 0.376105 0.254050 0.268016 0.118 Uiso 1 1 calc R U . . .
C17 C 0.5693(16) 0.2210(10) 0.2735(8) 0.117(3) Uani 1 1 d . . . . .
H17 H 0.553568 0.149340 0.286502 0.141 Uiso 1 1 calc R U . . .
C18 C 0.6965(13) 0.2661(11) 0.2661(8) 0.110(3) Uani 1 1 d . . . . .
H18 H 0.767922 0.225815 0.274849 0.132 Uiso 1 1 calc R U . . .
C19 C 0.7186(11) 0.3690(11) 0.2461(8) 0.112(3) Uani 1 1 d . . . . .
H19 H 0.806204 0.399112 0.241798 0.135 Uiso 1 1 calc R U . . .
C21 C -0.0073(7) 0.7353(8) 0.4374(6) 0.068(2) Uani 1 1 d . . . . .
C22 C -0.0652(8) 0.8275(7) 0.4915(7) 0.080(2) Uani 1 1 d . . . . .
H22 H -0.057807 0.899079 0.477851 0.096 Uiso 1 1 calc R U . . .
C23 C -0.1363(9) 0.8138(9) 0.5681(8) 0.100(3) Uani 1 1 d . . . . .
H23 H -0.176336 0.877126 0.606698 0.120 Uiso 1 1 calc R U . . .
C24 C -0.1477(9) 0.7101(10) 0.5871(8) 0.102(3) Uani 1 1 d . . . . .
H24 H -0.195267 0.699619 0.638019 0.122 Uiso 1 1 calc R U . . .
C25 C -0.0872(10) 0.6220(9) 0.5290(9) 0.112(3) Uani 1 1 d . . . . .
H25 H -0.094086 0.549631 0.541354 0.135 Uiso 1 1 calc R U . . .
N1 N 0.3452(6) 0.7095(6) 0.3215(5) 0.0727(17) Uani 1 1 d . . . . .
N20 N 0.6176(10) 0.4300(6) 0.2320(6) 0.098(2) Uani 1 1 d . . . . .
N26 N -0.0172(7) 0.6318(7) 0.4539(6) 0.094(2) Uani 1 1 d . . . . .
O1 O 0.2230(5) 0.4064(4) 0.2225(4) 0.0956(17) Uani 1 1 d . . . . .
O2 O 0.1112(5) 0.8763(4) 0.3441(4) 0.0914(16) Uani 1 1 d . . . . .
P1 P 0.3591(2) 0.46471(19) 0.21380(17) 0.0778(7) Uani 1 1 d . . . . .
P2 P 0.0878(2) 0.7470(2) 0.33862(17) 0.0729(7) Uani 1 1 d . . . . .
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
_geom_angle_publ_flag
N1 C1 P2 113.6(5) . . ?
N1 C2 P1 114.0(5) . . ?
C4 C3 P1 117.2(7) . . ?
C3 C4 C5 116.7(8) . 2_565 ?
C6 C5 C4 110.1(7) . 2_565 ?
C5 C6 P2 115.2(5) . . ?
N1 C7 C8 114.1(6) . . ?
C9 C8 C13 117.6(8) . . ?
C9 C8 C7 123.2(9) . . ?
C13 C8 C7 119.2(9) . . ?
C8 C9 C10 120.4(8) . . ?
C11 C10 C9 122.2(8) . . ?
C12 C11 C10 117.5(9) . . ?
C12 C11 C14 122.4(10) . . ?
C10 C11 C14 120.1(10) . . ?
C11 C12 C13 121.7(9) . . ?
C12 C13 C8 120.6(8) . . ?
N20 C15 C16 125.1(9) . . ?
N20 C15 P1 116.0(9) . . ?
C16 C15 P1 118.8(9) . . ?
C15 C16 C17 115.7(10) . . ?
C18 C17 C16 120.2(11) . . ?
C19 C18 C17 119.9(11) . . ?
C18 C19 N20 122.1(10) . . ?
N26 C21 C22 122.1(7) . . ?
N26 C21 P2 116.6(7) . . ?
C22 C21 P2 121.3(7) . . ?
C21 C22 C23 118.7(7) . . ?
C24 C23 C22 120.6(8) . . ?
C23 C24 C25 116.9(8) . . ?
C24 C25 N26 124.2(9) . . ?
C7 N1 C1 110.1(6) . . ?
C7 N1 C2 111.5(6) . . ?
C1 N1 C2 111.0(6) . . ?
C15 N20 C19 117.0(9) . . ?
C21 N26 C25 117.5(7) . . ?
O1 P1 C3 113.8(4) . . ?
O1 P1 C2 113.1(3) . . ?
C3 P1 C2 109.3(4) . . ?
O1 P1 C15 112.5(5) . . ?
C3 P1 C15 103.3(4) . . ?
C2 P1 C15 103.9(4) . . ?
O2 P2 C6 113.8(3) . . ?
O2 P2 C21 110.8(4) . . ?
C6 P2 C21 107.3(4) . . ?
O2 P2 C1 115.5(3) . . ?
C6 P2 C1 104.6(4) . . ?
C21 P2 C1 104.0(4) . . ?
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
C1 N1 1.463(8) . ?
C1 P2 1.813(8) . ?
C2 N1 1.474(8) . ?
C2 P1 1.774(7) . ?
C3 C4 1.446(10) . ?
C3 P1 1.767(7) . ?
C4 C5 1.518(10) 2_565 ?
C5 C6 1.514(10) . ?
C6 P2 1.746(7) . ?
C7 N1 1.460(8) . ?
C7 C8 1.486(10) . ?
C8 C9 1.378(10) . ?
C8 C13 1.392(10) . ?
C9 C10 1.380(9) . ?
C10 C11 1.372(11) . ?
C11 C12 1.360(10) . ?
C11 C14 1.509(10) . ?
C12 C13 1.385(10) . ?
C15 N20 1.319(10) . ?
C15 C16 1.378(10) . ?
C15 P1 1.816(9) . ?
C16 C17 1.383(12) . ?
C17 C18 1.362(11) . ?
C18 C19 1.345(11) . ?
C19 N20 1.350(11) . ?
C21 N26 1.323(8) . ?
C21 C22 1.344(9) . ?
C21 P2 1.792(8) . ?
C22 C23 1.389(10) . ?
C23 C24 1.342(10) . ?
C24 C25 1.348(10) . ?
C25 N26 1.349(10) . ?
O1 P1 1.501(6) . ?
O2 P2 1.493(5) . ?
