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#$Date: 2024-12-06 22:50:34 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296709 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/90/7249080.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_7249080
loop_
_publ_author_name
'Odubo, Favour E.'
'Muthuramesh, Snehashree'
'Zeller, Matthias'
'Rosokha, Sergiy V.'
_publ_section_title
;
 Anion-π interaction with alkenes: persistent complexes vs.
 irreversible reactions of anions with tetracyanoethylene.
;
_journal_issue                   31
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              21030
_journal_page_last               21039
_journal_paper_doi               10.1039/d4cp02573c
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C19 H18 P, C6 N4, Br'
_chemical_formula_sum            'C25 H18 Br N4 P'
_chemical_formula_weight         485.31
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-05-05 deposited with the CCDC.	2024-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                118.266(2)
_cell_angle_beta                 90.146(2)
_cell_angle_gamma                115.285(2)
_cell_formula_units_Z            2
_cell_length_a                   10.8503(4)
_cell_length_b                   11.6951(4)
_cell_length_c                   12.0077(4)
_cell_measurement_reflns_used    9831
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.8370
_cell_measurement_theta_min      2.5269
_cell_volume                     1172.64(8)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       'Apex4 v2022.10-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_structure_refinement
;  
SHELXL-2019/2 (Sheldrick, 2015a, 2019), 
SHELXLE Rev1573 (Hübschle et al., 2011)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015b)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_detector_type
'PhotonII charge-integrating pixel array (CPAD)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            67705
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.184
_diffrn_reflns_theta_min         2.527
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    1.840
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.5937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       plate
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         8967
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0263P)²+0.3971P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0630
_refine_ls_wR_factor_ref         0.0684
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7045
_reflns_number_total             8967
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cp02573c2.cif
_cod_data_source_block           RS237_0m
_cod_depositor_comments
'Adding full bibliography for 7249077--7249082.cif.'
_cod_database_code               7249080
_shelx_shelxl_version_number     2019/3
_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.
;
_shelx_estimated_absorpt_t_min   0.542
_shelx_estimated_absorpt_t_max   0.796
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
Br1 Br 0.34342(2) 0.16627(2) 0.51804(2) 0.02570(4) Uani 1 1 d . . . . .
P1 P 0.39556(3) 0.81173(3) 0.16074(3) 0.01802(6) Uani 1 1 d . . . . .
N1 N 0.6109(2) 0.30262(19) 0.33074(16) 0.0520(4) Uani 1 1 d . . . . .
N2 N 0.2059(2) 0.31185(19) 0.3324(2) 0.0602(5) Uani 1 1 d . . . . .
N3 N 0.06965(17) 0.27015(19) 0.76001(15) 0.0522(4) Uani 1 1 d . . . . .
N4 N -0.10433(17) 0.09367(19) 0.34578(16) 0.0526(4) Uani 1 1 d . . . . .
C1 C 0.5449(2) 0.35605(18) 0.38192(16) 0.0388(4) Uani 1 1 d . . . . .
C2 C 0.46666(18) 0.43131(16) 0.44547(16) 0.0343(3) Uani 1 1 d . . . . .
C3 C 0.3205(2) 0.36179(19) 0.38354(18) 0.0420(4) Uani 1 1 d . . . . .
C4 C 0.03660(17) 0.1781(2) 0.65258(16) 0.0393(3) Uani 1 1 d . . . . .
C5 C -0.00640(15) 0.06050(18) 0.51761(14) 0.0332(3) Uani 1 1 d . . . . .
C6 C -0.06193(16) 0.07875(19) 0.42206(16) 0.0385(3) Uani 1 1 d . . . . .
C7 C 0.52746(13) 0.97438(13) 0.30302(12) 0.0228(2) Uani 1 1 d . . . . .
H7A H 0.597917 1.037863 0.277563 0.034 Uiso 1 1 calc R U . . .
H7B H 0.573305 0.946047 0.348153 0.034 Uiso 1 1 calc R U . . .
H7C H 0.483767 1.028770 0.361676 0.034 Uiso 1 1 calc R U . . .
C8 C 0.27020(13) 0.69479(13) 0.20913(12) 0.0200(2) Uani 1 1 d . . . . .
C9 C 0.28797(16) 0.73576(17) 0.33963(14) 0.0334(3) Uani 1 1 d . . . . .
H9 H 0.365780 0.827463 0.404617 0.040 Uiso 1 1 calc R U . . .
C10 C 0.19177(18) 0.6424(2) 0.37477(16) 0.0408(4) Uani 1 1 d . . . . .
H10 H 0.203525 0.670927 0.464112 0.049 Uiso 1 1 calc R U . . .
C11 C 0.07931(17) 0.50861(18) 0.28100(16) 0.0359(3) Uani 1 1 d . . . . .
H11 H 0.014215 0.444798 0.305594 0.043 Uiso 1 1 calc R U . . .
C12 C 0.06137(16) 0.46731(16) 0.15072(15) 0.0331(3) Uani 1 1 d . . . . .
H12 H -0.015979 0.374910 0.086012 0.040 Uiso 1 1 calc R U . . .
C13 C 0.15556(14) 0.56005(15) 0.11460(13) 0.0273(3) Uani 1 1 d . . . . .
H13 H 0.142185 0.531966 0.025350 0.033 Uiso 1 1 calc R U . . .
C14 C 0.30296(13) 0.86256(13) 0.08425(12) 0.0212(2) Uani 1 1 d . . . . .
C15 C 0.31060(15) 0.84424(16) -0.03831(14) 0.0293(3) Uani 1 1 d . . . . .
H15 H 0.369092 0.807023 -0.083723 0.035 Uiso 1 1 calc R U . . .
C16 C 0.23204(17) 0.8808(2) -0.09383(17) 0.0377(3) Uani 1 1 d . . . . .
H16 H 0.234591 0.865791 -0.178580 0.045 Uiso 1 1 calc R U . . .
C17 C 0.15036(17) 0.93880(19) -0.02600(17) 0.0387(3) Uani 1 1 d . . . . .
H17 H 0.097168 0.963900 -0.064330 0.046 Uiso 1 1 calc R U . . .
C18 C 0.14514(18) 0.96084(18) 0.09766(16) 0.0375(3) Uani 1 1 d . . . . .
H18 H 0.090121 1.002705 0.144437 0.045 Uiso 1 1 calc R U . . .
C19 C 0.22056(15) 0.92154(16) 0.15284(13) 0.0294(3) Uani 1 1 d . . . . .
H19 H 0.216077 0.934722 0.236821 0.035 Uiso 1 1 calc R U . . .
C20 C 0.47454(14) 0.71620(13) 0.04741(12) 0.0218(2) Uani 1 1 d . . . . .
C21 C 0.61723(16) 0.76419(17) 0.08340(15) 0.0332(3) Uani 1 1 d . . . . .
H21 H 0.673246 0.847526 0.167860 0.040 Uiso 1 1 calc R U . . .
C22 C 0.6778(2) 0.6897(2) -0.00475(18) 0.0436(4) Uani 1 1 d . . . . .
H22 H 0.775571 0.722494 0.019545 0.052 Uiso 1 1 calc R U . . .
C23 C 0.5966(2) 0.56818(18) -0.12757(16) 0.0392(4) Uani 1 1 d . . . . .
H23 H 0.638931 0.518563 -0.187767 0.047 Uiso 1 1 calc R U . . .
C24 C 0.4547(2) 0.51890(17) -0.16287(15) 0.0391(4) Uani 1 1 d . . . . .
H24 H 0.398924 0.434113 -0.246758 0.047 Uiso 1 1 calc R U . . .
C25 C 0.39275(17) 0.59255(16) -0.07643(14) 0.0337(3) Uani 1 1 d . . . . .
H25 H 0.294871 0.558964 -0.101393 0.040 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'
Br Br -0.2901 2.4595 '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
C7 P1 C20 110.26(6) . . ?
C7 P1 C8 108.74(6) . . ?
C20 P1 C8 111.04(6) . . ?
C7 P1 C14 109.52(6) . . ?
C20 P1 C14 109.51(6) . . ?
C8 P1 C14 107.71(6) . . ?
N1 C1 C2 176.36(17) . . ?
C2 C2 C3 121.48(18) 2_666 . ?
C2 C2 C1 120.3(2) 2_666 . ?
C3 C2 C1 117.99(15) . . ?
N2 C3 C2 176.40(18) . . ?
N3 C4 C5 179.2(2) . . ?
C5 C5 C6 121.36(18) 2_556 . ?
C5 C5 C4 121.32(17) 2_556 . ?
C6 C5 C4 117.31(15) . . ?
N4 C6 C5 179.09(19) . . ?
P1 C7 H7A 109.5 . . ?
P1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
P1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 119.60(12) . . ?
C9 C8 P1 120.65(10) . . ?
C13 C8 P1 119.74(9) . . ?
C10 C9 C8 119.83(13) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C11 C10 C9 120.47(14) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 119.86(14) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 120.25(13) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 119.99(12) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C15 C14 C19 120.31(12) . . ?
C15 C14 P1 122.56(10) . . ?
C19 C14 P1 117.13(10) . . ?
C16 C15 C14 119.52(13) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 120.08(14) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.64(13) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C19 119.80(14) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C14 119.62(13) . . ?
C18 C19 H19 120.2 . . ?
C14 C19 H19 120.2 . . ?
C21 C20 C25 119.76(12) . . ?
C21 C20 P1 119.89(10) . . ?
C25 C20 P1 120.35(10) . . ?
C20 C21 C22 119.63(14) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C23 C22 C21 120.35(16) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C24 C23 C22 120.18(13) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 120.21(14) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C20 119.85(15) . . ?
C24 C25 H25 120.1 . . ?
C20 C25 H25 120.1 . . ?
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
P1 C7 1.7803(12) . ?
P1 C20 1.7939(12) . ?
P1 C8 1.7960(13) . ?
P1 C14 1.7970(12) . ?
N1 C1 1.141(2) . ?
N2 C3 1.141(2) . ?
N3 C4 1.142(2) . ?
N4 C6 1.140(2) . ?
C1 C2 1.443(2) . ?
C2 C2 1.352(3) 2_666 ?
C2 C3 1.432(3) . ?
C4 C5 1.440(2) . ?
C5 C5 1.342(3) 2_556 ?
C5 C6 1.436(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.3895(18) . ?
C8 C13 1.3940(18) . ?
C9 C10 1.387(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.378(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.3913(18) . ?
C14 C19 1.3950(18) . ?
C15 C16 1.3899(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.3881(19) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.3868(19) . ?
C20 C25 1.3965(18) . ?
C21 C22 1.389(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.382(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.374(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.387(2) . ?
C24 H24 0.9500 . ?
C25 H25 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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 P1 C8 C9 -1.69(13) . . . . ?
C20 P1 C8 C9 119.80(12) . . . . ?
C14 P1 C8 C9 -120.30(12) . . . . ?
C7 P1 C8 C13 179.71(10) . . . . ?
C20 P1 C8 C13 -58.80(12) . . . . ?
C14 P1 C8 C13 61.10(11) . . . . ?
C13 C8 C9 C10 0.1(2) . . . . ?
P1 C8 C9 C10 -178.53(13) . . . . ?
C8 C9 C10 C11 0.6(3) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C10 C11 C12 C13 -0.2(2) . . . . ?
C11 C12 C13 C8 0.9(2) . . . . ?
C9 C8 C13 C12 -0.8(2) . . . . ?
P1 C8 C13 C12 177.83(11) . . . . ?
C7 P1 C14 C15 113.68(11) . . . . ?
C20 P1 C14 C15 -7.35(13) . . . . ?
C8 P1 C14 C15 -128.22(11) . . . . ?
C7 P1 C14 C19 -66.71(12) . . . . ?
C20 P1 C14 C19 172.26(10) . . . . ?
C8 P1 C14 C19 51.40(12) . . . . ?
C19 C14 C15 C16 -2.0(2) . . . . ?
P1 C14 C15 C16 177.60(12) . . . . ?
C14 C15 C16 C17 1.9(2) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C16 C17 C18 C19 -1.3(3) . . . . ?
C17 C18 C19 C14 1.1(2) . . . . ?
C15 C14 C19 C18 0.5(2) . . . . ?
P1 C14 C19 C18 -179.11(12) . . . . ?
C7 P1 C20 C21 6.54(13) . . . . ?
C8 P1 C20 C21 -114.06(11) . . . . ?
C14 P1 C20 C21 127.12(11) . . . . ?
C7 P1 C20 C25 -174.23(11) . . . . ?
C8 P1 C20 C25 65.17(12) . . . . ?
C14 P1 C20 C25 -53.65(12) . . . . ?
C25 C20 C21 C22 0.7(2) . . . . ?
P1 C20 C21 C22 179.96(12) . . . . ?
C20 C21 C22 C23 -0.2(3) . . . . ?
C21 C22 C23 C24 -0.8(3) . . . . ?
C22 C23 C24 C25 1.3(2) . . . . ?
C23 C24 C25 C20 -0.7(2) . . . . ?
C21 C20 C25 C24 -0.3(2) . . . . ?
P1 C20 C25 C24 -179.52(12) . . . . ?
