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#$Date: 2017-09-02 05:52:45 +0300 (Sat, 02 Sep 2017) $
#$Revision: 200107 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/40/7044078.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_7044078
loop_
_publ_author_name
'Wittmann, T. I.'
'Musina, E. I.'
'Krivolapov, D. B.'
'Litvinov, I. A.'
'Kondrashova, S. A.'
'Latypov, Sh. K.'
'Karasik, A. A.'
'Sinyashin, O. G.'
_publ_section_title
;
 Covalent self-assembly of the specific RSSR isomer of 14-membered
 tetrakisphosphine
;
_journal_name_full               'Dalton Trans.'
_journal_paper_doi               10.1039/C7DT03010J
_journal_year                    2017
_chemical_formula_sum            'C42 H58 N2 P4'
_chemical_formula_weight         714.78
_chemical_name_systematic
1,8-di(iso-pentyl)-3,6,10,13-tetraphenyl-1,8-diaza-3,6,10,13-tetraphosphacyclotetradecane
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-07-07 deposited with the CCDC.
2017-08-21 downloaded from the CCDC.
;
_cell_angle_alpha                112.941(10)
_cell_angle_beta                 95.282(11)
_cell_angle_gamma                96.975(11)
_cell_formula_units_Z            1
_cell_length_a                   5.623(5)
_cell_length_b                   13.319(11)
_cell_length_c                   14.842(13)
_cell_measurement_reflns_used    1558
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.35
_cell_measurement_theta_min      2.68
_cell_volume                     1004.2(15)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.986
_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  0.0609
_diffrn_reflns_av_unetI/netI     0.0960
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8329
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_min         1.507
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3873
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0643
_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)+(0.0928P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1526
_refine_ls_wR_factor_ref         0.1827
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2293
_reflns_number_total             3873
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7dt03010j2.cif
_cod_data_source_block           shelx
_cod_database_code               7044078
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.919
_shelx_estimated_absorpt_t_max   0.972
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
P1 P 0.27664(16) 0.24895(8) 0.42538(7) 0.0430(3) Uani 1 1 d . .
P2 P 0.51334(16) 0.47992(7) 0.64087(7) 0.0415(3) Uani 1 1 d . .
C13 C -0.0713(10) -0.1159(4) 0.3260(4) 0.0769(14) Uani 1 1 d . .
H13 H -0.1363 -0.1902 0.3060 0.092 Uiso 1 1 calc R U
C14 C 0.1505(12) -0.0739(4) 0.3793(5) 0.116(2) Uani 1 1 d . .
H14 H 0.2384 -0.1191 0.3983 0.140 Uiso 1 1 calc R U
C15 C 0.2498(9) 0.0353(4) 0.4063(4) 0.0843(16) Uani 1 1 d . .
H15 H 0.4062 0.0616 0.4413 0.101 Uiso 1 1 calc R U
C10 C 0.1280(7) 0.1048(3) 0.3836(3) 0.0470(9) Uani 1 1 d . .
C2 C 0.1295(6) 0.2999(3) 0.3372(3) 0.0417(8) Uani 1 1 d . .
H2A H -0.0276 0.2530 0.3083 0.050 Uiso 1 1 calc R U
H2B H 0.0993 0.3735 0.3761 0.050 Uiso 1 1 calc R U
N1 N 0.2495(5) 0.3061(2) 0.2555(2) 0.0407(7) Uani 1 1 d . .
C1 C 0.4928(6) 0.3702(3) 0.2909(3) 0.0461(9) Uani 1 1 d . .
H1A H 0.5789 0.3599 0.2351 0.055 Uiso 1 1 calc R U
H1B H 0.5797 0.3436 0.3343 0.055 Uiso 1 1 calc R U
C4 C 0.1921(6) 0.4395(3) 0.5834(3) 0.0428(9) Uani 1 1 d . .
H4A H 0.0928 0.4682 0.6347 0.051 Uiso 1 1 calc R U
H4B H 0.1665 0.4741 0.5375 0.051 Uiso 1 1 calc R U
C3 C 0.1062(6) 0.3154(3) 0.5283(3) 0.0450(9) Uani 1 1 d . .
H3A H -0.0643 0.3020 0.5018 0.054 Uiso 1 1 calc R U
H3B H 0.1222 0.2810 0.5749 0.054 Uiso 1 1 calc R U
C19 C 0.5082(10) 0.3479(4) 0.8850(3) 0.0745(13) Uani 1 1 d . .
H19 H 0.5095 0.3202 0.9337 0.089 Uiso 1 1 calc R U
C20 C 0.3477(8) 0.4131(4) 0.8790(3) 0.0688(12) Uani 1 1 d . .
H20 H 0.2383 0.4304 0.9239 0.083 Uiso 1 1 calc R U
C21 C 0.3436(7) 0.4545(3) 0.8076(3) 0.0545(10) Uani 1 1 d . .
H21 H 0.2317 0.4995 0.8045 0.065 Uiso 1 1 calc R U
C16 C 0.5059(6) 0.4295(3) 0.7393(3) 0.0426(8) Uani 1 1 d . .
C17 C 0.6664(7) 0.3631(3) 0.7471(3) 0.0566(10) Uani 1 1 d . .
H17 H 0.7765 0.3449 0.7027 0.068 Uiso 1 1 calc R U
C18 C 0.6689(8) 0.3224(4) 0.8193(4) 0.0759(13) Uani 1 1 d . .
H18 H 0.7803 0.2775 0.8233 0.091 Uiso 1 1 calc R U
C5 C 0.2249(7) 0.2012(3) 0.1682(3) 0.0477(9) Uani 1 1 d . .
H5 H 0.0625 0.1604 0.1616 0.057 Uiso 1 1 calc R U
C6 C 0.2317(8) 0.2244(4) 0.0759(3) 0.0630(11) Uani 1 1 d . .
H6A H 0.3888 0.2672 0.0813 0.076 Uiso 1 1 calc R U
H6B H 0.2159 0.1546 0.0190 0.076 Uiso 1 1 calc R U
C8 C 0.0397(9) 0.2853(4) 0.0578(3) 0.0816(14) Uani 1 1 d . .
H8A H -0.1158 0.2483 0.0601 0.122 Uiso 1 1 calc R U
H8B H 0.0412 0.2872 -0.0061 0.122 Uiso 1 1 calc R U
H8C H 0.0701 0.3595 0.1079 0.122 Uiso 1 1 calc R U
C7 C 0.4026(7) 0.1268(3) 0.1758(3) 0.0577(11) Uani 1 1 d . .
H7A H 0.4334 0.1352 0.2440 0.069 Uiso 1 1 calc R U
H7B H 0.5549 0.1508 0.1584 0.069 Uiso 1 1 calc R U
C9 C 0.3141(10) 0.0047(4) 0.1094(4) 0.0926(16) Uani 1 1 d . .
H9A H 0.1654 -0.0204 0.1272 0.139 Uiso 1 1 calc R U
H9B H 0.4343 -0.0377 0.1177 0.139 Uiso 1 1 calc R U
H9C H 0.2870 -0.0048 0.0415 0.139 Uiso 1 1 calc R U
C12 C -0.1953(10) -0.0488(4) 0.3026(4) 0.102(2) Uani 1 1 d . .
H12 H -0.3493 -0.0764 0.2655 0.122 Uiso 1 1 calc R U
C11 C -0.0997(9) 0.0608(4) 0.3323(4) 0.0955(19) Uani 1 1 d . .
H11 H -0.1933 0.1065 0.3169 0.115 Uiso 1 1 calc R U
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'
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
C10 P1 C3 99.45(16) . .
C10 P1 C2 105.04(17) . .
C3 P1 C2 96.43(17) . .
C16 P2 C4 100.85(16) . .
C16 P2 C1 102.12(17) . 2_666
C4 P2 C1 96.68(16) . 2_666
C12 C13 C14 118.2(4) . .
C12 C13 H13 120.9 . .
C14 C13 H13 120.9 . .
C13 C14 C15 120.9(5) . .
C13 C14 H14 119.6 . .
C15 C14 H14 119.6 . .
C10 C15 C14 121.9(5) . .
C10 C15 H15 119.0 . .
C14 C15 H15 119.0 . .
C15 C10 C11 115.9(4) . .
C15 C10 P1 118.1(3) . .
C11 C10 P1 126.0(3) . .
N1 C2 P1 120.5(2) . .
N1 C2 H2A 107.2 . .
P1 C2 H2A 107.2 . .
N1 C2 H2B 107.2 . .
P1 C2 H2B 107.2 . .
H2A C2 H2B 106.8 . .
C1 N1 C2 111.5(3) . .
C1 N1 C5 115.8(3) . .
C2 N1 C5 115.4(3) . .
N1 C1 P2 111.5(2) . 2_666
N1 C1 H1A 109.3 . .
P2 C1 H1A 109.3 2_666 .
N1 C1 H1B 109.3 . .
P2 C1 H1B 109.3 2_666 .
H1A C1 H1B 108.0 . .
C3 C4 P2 114.7(2) . .
C3 C4 H4A 108.6 . .
P2 C4 H4A 108.6 . .
C3 C4 H4B 108.6 . .
P2 C4 H4B 108.6 . .
H4A C4 H4B 107.6 . .
C4 C3 P1 113.5(2) . .
C4 C3 H3A 108.9 . .
P1 C3 H3A 108.9 . .
C4 C3 H3B 108.9 . .
P1 C3 H3B 108.9 . .
H3A C3 H3B 107.7 . .
C20 C19 C18 119.8(4) . .
C20 C19 H19 120.1 . .
C18 C19 H19 120.1 . .
C19 C20 C21 120.8(4) . .
C19 C20 H20 119.6 . .
C21 C20 H20 119.6 . .
C20 C21 C16 120.6(4) . .
C20 C21 H21 119.7 . .
C16 C21 H21 119.7 . .
C17 C16 C21 117.3(4) . .
C17 C16 P2 118.9(3) . .
C21 C16 P2 123.8(3) . .
C16 C17 C18 121.5(4) . .
C16 C17 H17 119.2 . .
C18 C17 H17 119.2 . .
C19 C18 C17 120.1(4) . .
C19 C18 H18 120.0 . .
C17 C18 H18 120.0 . .
N1 C5 C7 114.8(3) . .
N1 C5 C6 109.5(3) . .
C7 C5 C6 112.3(3) . .
N1 C5 H5 106.6 . .
C7 C5 H5 106.6 . .
C6 C5 H5 106.6 . .
C8 C6 C5 114.6(3) . .
C8 C6 H6A 108.6 . .
C5 C6 H6A 108.6 . .
C8 C6 H6B 108.6 . .
C5 C6 H6B 108.6 . .
H6A C6 H6B 107.6 . .
C6 C8 H8A 109.5 . .
C6 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C6 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C5 C7 C9 113.6(4) . .
C5 C7 H7A 108.8 . .
C9 C7 H7A 108.8 . .
C5 C7 H7B 108.8 . .
C9 C7 H7B 108.8 . .
H7A C7 H7B 107.7 . .
C7 C9 H9A 109.5 . .
C7 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C7 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C13 C12 C11 120.9(5) . .
C13 C12 H12 119.6 . .
C11 C12 H12 119.6 . .
C10 C11 C12 122.1(5) . .
C10 C11 H11 119.0 . .
C12 C11 H11 119.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C10 1.832(4) .
P1 C3 1.859(4) .
P1 C2 1.867(4) .
P2 C16 1.833(4) .
P2 C4 1.844(4) .
P2 C1 1.860(4) 2_666
C13 C12 1.325(7) .
C13 C14 1.341(7) .
C13 H13 0.9300 .
C14 C15 1.377(6) .
C14 H14 0.9300 .
C15 C10 1.338(6) .
C15 H15 0.9300 .
C10 C11 1.361(6) .
C2 N1 1.467(4) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
N1 C1 1.453(4) .
N1 C5 1.470(4) .
C1 P2 1.860(4) 2_666
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C4 C3 1.520(5) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C19 C20 1.347(6) .
C19 C18 1.364(6) .
C19 H19 0.9300 .
C20 C21 1.372(6) .
C20 H20 0.9300 .
C21 C16 1.397(5) .
C21 H21 0.9300 .
C16 C17 1.365(5) .
C17 C18 1.375(6) .
C17 H17 0.9300 .
C18 H18 0.9300 .
C5 C7 1.517(5) .
C5 C6 1.520(5) .
C5 H5 0.9800 .
C6 C8 1.491(6) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C7 C9 1.526(6) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C12 C11 1.370(6) .
C12 H12 0.9300 .
C11 H11 0.9300 .
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
C12 C13 C14 C15 -2.0(10) . .
C13 C14 C15 C10 2.2(10) . .
C14 C15 C10 C11 0.0(8) . .
C14 C15 C10 P1 178.9(5) . .
C3 P1 C10 C15 -105.6(4) . .
C2 P1 C10 C15 155.1(4) . .
C3 P1 C10 C11 73.2(4) . .
C2 P1 C10 C11 -26.1(5) . .
C10 P1 C2 N1 -100.2(3) . .
C3 P1 C2 N1 158.2(3) . .
P1 C2 N1 C1 -54.2(4) . .
P1 C2 N1 C5 80.6(3) . .
C2 N1 C1 P2 -71.0(3) . 2_666
C5 N1 C1 P2 154.4(2) . 2_666
C16 P2 C4 C3 -68.9(3) . .
C1 P2 C4 C3 -172.6(2) 2_666 .
P2 C4 C3 P1 -59.6(3) . .
C10 P1 C3 C4 178.1(3) . .
C2 P1 C3 C4 -75.4(3) . .
C18 C19 C20 C21 0.0(8) . .
C19 C20 C21 C16 0.1(7) . .
C20 C21 C16 C17 0.0(6) . .
C20 C21 C16 P2 179.6(3) . .
C4 P2 C16 C17 128.1(3) . .
C1 P2 C16 C17 -132.5(3) 2_666 .
C4 P2 C16 C21 -51.5(4) . .
C1 P2 C16 C21 47.8(3) 2_666 .
C21 C16 C17 C18 -0.1(6) . .
P2 C16 C17 C18 -179.8(3) . .
C20 C19 C18 C17 -0.2(8) . .
C16 C17 C18 C19 0.2(7) . .
C1 N1 C5 C7 50.5(4) . .
C2 N1 C5 C7 -82.3(4) . .
C1 N1 C5 C6 -76.9(4) . .
C2 N1 C5 C6 150.3(3) . .
N1 C5 C6 C8 -58.6(5) . .
C7 C5 C6 C8 172.7(4) . .
N1 C5 C7 C9 155.7(3) . .
C6 C5 C7 C9 -78.3(5) . .
C14 C13 C12 C11 -0.2(10) . .
C15 C10 C11 C12 -2.2(8) . .
P1 C10 C11 C12 178.9(4) . .
C13 C12 C11 C10 2.4(10) . .
