#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:18:46 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257792 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/96/7059669.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_7059669
loop_
_publ_author_name
'Ling, Irene'
'Skelton, Brian W.'
'Sobolev, Alexandre N.'
'Alias, Yatimah'
'Khor, Zong Chin'
'Raston, Colin L.'
_publ_section_title
;
 Effect of anions on the solid-state interplay of symmetric and
 unsymmetric phosphonium cations
;
_journal_issue                   25
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10220
_journal_page_last               10228
_journal_paper_doi               10.1039/D0NJ01975E
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C25 H22 P, C2 N3'
_chemical_formula_sum            'C27 H22 N3 P'
_chemical_formula_weight         419.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-12-02 deposited with the CCDC.	2020-05-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.094(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2149(4)
_cell_length_b                   16.9072(5)
_cell_length_c                   11.7093(5)
_cell_measurement_reflns_used    8759
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.2
_cell_measurement_theta_min      3.8
_cell_volume                     2207.68(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'X-Seed v. 4.0 (Barbour, 2001)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2015/1 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4738
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-R Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24169
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.315
_diffrn_reflns_theta_max         67.315
_diffrn_reflns_theta_min         4.611
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.239
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       plate
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3959
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0421
_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)+(0.0500P)²+1.4500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1091
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3298
_reflns_number_total             3959
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj01975e1.cif
_cod_data_source_block           090720g
_cod_depositor_comments
;Adding full bibliography for 7059666--7059672.cif.

 Adding full bibliography for 7059666--7059672.cif.
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7059669
_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.
;
_shelx_estimated_absorpt_t_min   0.657
_shelx_estimated_absorpt_t_max   0.918
loop_
_space_group_symop_operation_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_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
P1 P 0.29988(4) 0.25707(3) 0.30497(4) 0.02191(14) Uani 1 1 d . . . . .
C10 C 0.36007(16) 0.26450(11) 0.45442(16) 0.0251(4) Uani 1 1 d . . . . .
H10A H 0.447976 0.272121 0.459022 0.030 Uiso 1 1 calc R U . . .
H10B H 0.325269 0.311443 0.489035 0.030 Uiso 1 1 calc R U . . .
C11 C 0.36664(16) 0.17302(11) 0.24374(15) 0.0242(4) Uani 1 1 d . . . . .
C12 C 0.4705(2) 0.18412(13) 0.18995(19) 0.0374(5) Uani 1 1 d . . . . .
H12 H 0.501375 0.235856 0.181346 0.045 Uiso 1 1 calc R U . . .
C13 C 0.5284(2) 0.11933(14) 0.1492(2) 0.0438(6) Uani 1 1 d . . . . .
H13 H 0.599763 0.126568 0.113411 0.053 Uiso 1 1 calc R U . . .
C14 C 0.4826(2) 0.04397(13) 0.16038(19) 0.0400(5) Uani 1 1 d . . . . .
H14 H 0.520982 -0.000113 0.129697 0.048 Uiso 1 1 calc R U . . .
C15 C 0.38145(19) 0.03275(12) 0.2160(2) 0.0379(5) Uani 1 1 d . . . . .
H15 H 0.350896 -0.019096 0.224329 0.045 Uiso 1 1 calc R U . . .
C16 C 0.32438(17) 0.09694(11) 0.25958(18) 0.0304(4) Uani 1 1 d . . . . .
H16 H 0.256443 0.088987 0.300264 0.036 Uiso 1 1 calc R U . . .
C21 C 0.13929(16) 0.24945(11) 0.29774(15) 0.0228(4) Uani 1 1 d . . . . .
C22 C 0.08110(17) 0.30468(11) 0.36176(17) 0.0274(4) Uani 1 1 d . . . . .
H22 H 0.125453 0.345541 0.402549 0.033 Uiso 1 1 calc R U . . .
C23 C -0.04194(17) 0.29910(12) 0.36500(17) 0.0296(4) Uani 1 1 d . . . . .
H23 H -0.082104 0.336480 0.407897 0.035 Uiso 1 1 calc R U . . .
C24 C -0.10664(16) 0.23907(12) 0.30577(17) 0.0283(4) Uani 1 1 d . . . . .
H24 H -0.190376 0.234376 0.310582 0.034 Uiso 1 1 calc R U . . .
C25 C -0.04939(17) 0.18605(11) 0.23972(17) 0.0278(4) Uani 1 1 d . . . . .
H25 H -0.094336 0.145969 0.197732 0.033 Uiso 1 1 calc R U . . .
C26 C 0.07381(16) 0.19135(11) 0.23471(16) 0.0253(4) Uani 1 1 d . . . . .
H26 H 0.112906 0.155499 0.188525 0.030 Uiso 1 1 calc R U . . .
C31 C 0.33975(16) 0.34473(11) 0.23047(16) 0.0253(4) Uani 1 1 d . . . . .
C32 C 0.40151(16) 0.40605(11) 0.28815(17) 0.0269(4) Uani 1 1 d . . . . .
H32 H 0.423910 0.402387 0.368528 0.032 Uiso 1 1 calc R U . . .
C33 C 0.43076(18) 0.47312(11) 0.22822(19) 0.0318(4) Uani 1 1 d . . . . .
H33 H 0.473547 0.515273 0.267459 0.038 Uiso 1 1 calc R U . . .
C34 C 0.39737(19) 0.47822(12) 0.1114(2) 0.0362(5) Uani 1 1 d . . . . .
H34 H 0.417124 0.524089 0.070527 0.043 Uiso 1 1 calc R U . . .
C35 C 0.3352(2) 0.41682(13) 0.05361(19) 0.0382(5) Uani 1 1 d . . . . .
H35 H 0.312756 0.420842 -0.026719 0.046 Uiso 1 1 calc R U . . .
C36 C 0.30566(19) 0.34966(12) 0.11219(18) 0.0319(4) Uani 1 1 d . . . . .
H36 H 0.262907 0.307587 0.072699 0.038 Uiso 1 1 calc R U . . .
C41 C 0.33354(16) 0.19193(11) 0.52224(16) 0.0253(4) Uani 1 1 d . . . . .
C42 C 0.4160(2) 0.13072(13) 0.53585(18) 0.0347(5) Uani 1 1 d . . . . .
H42 H 0.488310 0.133898 0.500586 0.042 Uiso 1 1 calc R U . . .
C43 C 0.3933(2) 0.06468(13) 0.60087(19) 0.0436(6) Uani 1 1 d . . . . .
H43 H 0.449606 0.022530 0.608800 0.052 Uiso 1 1 calc R U . . .
C44 C 0.2897(2) 0.06008(13) 0.65382(18) 0.0422(5) Uani 1 1 d . . . . .
H44 H 0.275355 0.015332 0.699512 0.051 Uiso 1 1 calc R U . . .
C45 C 0.2067(2) 0.12026(13) 0.64060(18) 0.0377(5) Uani 1 1 d . . . . .
H45 H 0.134951 0.116893 0.676718 0.045 Uiso 1 1 calc R U . . .
C46 C 0.22803(18) 0.18595(12) 0.57442(17) 0.0302(4) Uani 1 1 d . . . . .
H46 H 0.170137 0.227087 0.564704 0.036 Uiso 1 1 calc R U . . .
N1 N 0.66152(15) 0.29661(11) 0.43797(16) 0.0362(4) Uani 1 1 d . . . . .
N2 N 0.72693(16) 0.55571(11) 0.45248(16) 0.0360(4) Uani 1 1 d . . . . .
N3 N 0.63141(16) 0.43194(10) 0.50685(15) 0.0334(4) Uani 1 1 d . . . . .
C1 C 0.65342(16) 0.36197(12) 0.46620(16) 0.0275(4) Uani 1 1 d . . . . .
C2 C 0.68545(17) 0.49532(12) 0.47396(17) 0.0284(4) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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
C11 P1 C21 112.54(9) . . ?
C11 P1 C31 108.87(9) . . ?
C21 P1 C31 109.59(8) . . ?
C11 P1 C10 108.23(8) . . ?
C21 P1 C10 108.60(8) . . ?
C31 P1 C10 108.95(9) . . ?
C41 C10 P1 112.21(13) . . ?
C41 C10 H10A 109.2 . . ?
P1 C10 H10A 109.2 . . ?
C41 C10 H10B 109.2 . . ?
P1 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C16 C11 C12 119.85(18) . . ?
C16 C11 P1 121.19(14) . . ?
C12 C11 P1 118.60(15) . . ?
C13 C12 C11 119.6(2) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 120.2(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 120.17(19) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.1(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 119.90(19) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
C26 C21 C22 120.32(17) . . ?
C26 C21 P1 123.05(14) . . ?
C22 C21 P1 116.62(14) . . ?
C23 C22 C21 119.37(18) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 120.27(18) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C25 C24 C23 120.19(17) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 120.19(18) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C21 C26 C25 119.58(17) . . ?
C21 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C32 C31 C36 120.58(17) . . ?
C32 C31 P1 121.20(15) . . ?
C36 C31 P1 118.21(15) . . ?
C31 C32 C33 119.84(19) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
C34 C33 C32 119.8(2) . . ?
C34 C33 H33 120.1 . . ?
C32 C33 H33 120.1 . . ?
C33 C34 C35 120.40(19) . . ?
C33 C34 H34 119.8 . . ?
C35 C34 H34 119.8 . . ?
C36 C35 C34 120.4(2) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C35 C36 C31 119.0(2) . . ?
C35 C36 H36 120.5 . . ?
C31 C36 H36 120.5 . . ?
C42 C41 C46 118.89(18) . . ?
C42 C41 C10 120.11(17) . . ?
C46 C41 C10 120.98(17) . . ?
C41 C42 C43 120.3(2) . . ?
C41 C42 H42 119.9 . . ?
C43 C42 H42 119.9 . . ?
C44 C43 C42 120.3(2) . . ?
C44 C43 H43 119.9 . . ?
C42 C43 H43 119.9 . . ?
C45 C44 C43 120.0(2) . . ?
C45 C44 H44 120.0 . . ?
C43 C44 H44 120.0 . . ?
C44 C45 C46 120.0(2) . . ?
C44 C45 H45 120.0 . . ?
C46 C45 H45 120.0 . . ?
C45 C46 C41 120.49(19) . . ?
C45 C46 H46 119.8 . . ?
C41 C46 H46 119.8 . . ?
C1 N3 C2 121.47(17) . . ?
N1 C1 N3 171.4(2) . . ?
N2 C2 N3 173.1(2) . . ?
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 C11 1.7911(18) . ?
P1 C21 1.7986(18) . ?
P1 C31 1.8000(18) . ?
P1 C10 1.8120(19) . ?
C10 C41 1.508(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.390(3) . ?
C11 C12 1.395(3) . ?
C12 C13 1.384(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.391(3) . ?
C21 C22 1.401(3) . ?
C22 C23 1.388(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.385(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.392(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C32 1.383(3) . ?
C31 C36 1.400(3) . ?
C32 C33 1.391(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.382(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.386(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.385(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C42 1.386(3) . ?
C41 C46 1.392(3) . ?
C42 C43 1.390(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.377(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.376(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.389(3) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
N1 C1 1.160(3) . ?
N2 C2 1.161(3) . ?
N3 C1 1.308(3) . ?
N3 C2 1.309(3) . ?
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
C11 P1 C10 C41 -60.06(15) . . . . ?
C21 P1 C10 C41 62.39(15) . . . . ?
C31 P1 C10 C41 -178.30(12) . . . . ?
C21 P1 C11 C16 -39.18(18) . . . . ?
C31 P1 C11 C16 -160.88(15) . . . . ?
C10 P1 C11 C16 80.83(17) . . . . ?
C21 P1 C11 C12 147.67(16) . . . . ?
C31 P1 C11 C12 25.98(19) . . . . ?
C10 P1 C11 C12 -92.31(17) . . . . ?
C16 C11 C12 C13 2.2(3) . . . . ?
P1 C11 C12 C13 175.47(18) . . . . ?
C11 C12 C13 C14 0.8(4) . . . . ?
C12 C13 C14 C15 -2.4(4) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C14 C15 C16 C11 2.3(3) . . . . ?
C12 C11 C16 C15 -3.8(3) . . . . ?
P1 C11 C16 C15 -176.85(16) . . . . ?
C11 P1 C21 C26 -10.06(18) . . . . ?
C31 P1 C21 C26 111.23(16) . . . . ?
C10 P1 C21 C26 -129.86(16) . . . . ?
C11 P1 C21 C22 168.55(14) . . . . ?
C31 P1 C21 C22 -70.17(16) . . . . ?
C10 P1 C21 C22 48.74(16) . . . . ?
C26 C21 C22 C23 2.3(3) . . . . ?
P1 C21 C22 C23 -176.33(15) . . . . ?
C21 C22 C23 C24 0.3(3) . . . . ?
C22 C23 C24 C25 -2.3(3) . . . . ?
C23 C24 C25 C26 1.7(3) . . . . ?
C22 C21 C26 C25 -2.9(3) . . . . ?
P1 C21 C26 C25 175.62(14) . . . . ?
C24 C25 C26 C21 0.9(3) . . . . ?
C11 P1 C31 C32 -120.77(15) . . . . ?
C21 P1 C31 C32 115.76(16) . . . . ?
C10 P1 C31 C32 -2.93(17) . . . . ?
C11 P1 C31 C36 59.77(17) . . . . ?
C21 P1 C31 C36 -63.71(17) . . . . ?
C10 P1 C31 C36 177.60(14) . . . . ?
C36 C31 C32 C33 -0.4(3) . . . . ?
P1 C31 C32 C33 -179.83(14) . . . . ?
C31 C32 C33 C34 0.3(3) . . . . ?
C32 C33 C34 C35 -0.2(3) . . . . ?
C33 C34 C35 C36 0.1(3) . . . . ?
C34 C35 C36 C31 -0.1(3) . . . . ?
C32 C31 C36 C35 0.3(3) . . . . ?
P1 C31 C36 C35 179.76(15) . . . . ?
P1 C10 C41 C42 93.24(19) . . . . ?
P1 C10 C41 C46 -88.37(19) . . . . ?
C46 C41 C42 C43 -0.2(3) . . . . ?
C10 C41 C42 C43 178.26(19) . . . . ?
C41 C42 C43 C44 -1.0(3) . . . . ?
C42 C43 C44 C45 1.3(3) . . . . ?
C43 C44 C45 C46 -0.4(3) . . . . ?
C44 C45 C46 C41 -0.8(3) . . . . ?
C42 C41 C46 C45 1.1(3) . . . . ?
C10 C41 C46 C45 -177.35(18) . . . . ?
