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#$Date: 2024-08-05 21:12:58 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293778 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/20/1572041.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_1572041
loop_
_publ_author_name
'Nascimento, Mitchell A.'
'LaPierre, Etienne A.'
'Patrick, Brian O.'
'Watson, Jade E. T.'
'Watanabe, Lara'
'Rawson, Jeremy'
'Hering-Junghans, Christian'
'Manners, Ian'
_publ_section_title
;
 1,3-Dipolar cyclisation reactions of nitriles with sterically encumbered
 cyclic triphosphanes: synthesis and electronic structure of
 phosphorus-rich heterocycles with tunable colour.
;
_journal_issue                   30
_journal_name_full               'Chemical science'
_journal_page_first              12006
_journal_page_last               12016
_journal_paper_doi               10.1039/d4sc02497d
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C43 H56 N1 P3'
_chemical_formula_sum            'C43 H56 N P3'
_chemical_formula_weight         679.79
_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
_audit_update_record
;
2023-09-05 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                86.071(2)
_cell_angle_beta                 89.119(3)
_cell_angle_gamma                79.852(2)
_cell_formula_units_Z            2
_cell_length_a                   8.7516(4)
_cell_length_b                   11.3824(5)
_cell_length_c                   20.2888(11)
_cell_measurement_reflns_used    9994
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.43
_cell_measurement_theta_min      2.36
_cell_volume                     1984.75(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'LinXTL v. 5.9.9 (Spasyuk, 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_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  0.0308
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            28331
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.431
_diffrn_reflns_theta_min         1.006
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  .7238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         8107
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0373
_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)+(0.0373P)²+0.7620P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0925
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6576
_reflns_number_total             8107
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc02497d4.cif
_cod_data_source_block           im024_a
_cod_depositor_comments
'Adding full bibliography for 1572027--1572043.cif.'
_cod_database_code               1572041
_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   0.958
_shelx_estimated_absorpt_t_max   0.988
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 0.27625(17) 0.66284(13) 0.17307(8) 0.0195(3) Uani 1 1 d . . . . .
C2 C 0.27374(19) 0.60490(15) 0.10910(8) 0.0260(4) Uani 1 1 d . . . . .
C3 C 0.1938(3) 0.66799(18) 0.05535(10) 0.0433(5) Uani 1 1 d . . . . .
H3 H 0.143288 0.746239 0.059277 0.052 Uiso 1 1 calc R U . . .
C4 C 0.1886(3) 0.6155(2) -0.00393(11) 0.0608(7) Uani 1 1 d . . . . .
H4 H 0.134816 0.658661 -0.039523 0.073 Uiso 1 1 calc R U . . .
C5 C 0.2627(3) 0.4994(2) -0.01052(11) 0.0559(6) Uani 1 1 d . . . . .
H5 H 0.259376 0.464531 -0.050482 0.067 Uiso 1 1 calc R U . . .
C6 C 0.3415(2) 0.43556(18) 0.04230(10) 0.0455(5) Uani 1 1 d . . . . .
H6 H 0.390644 0.357047 0.038123 0.055 Uiso 1 1 calc R U . . .
C7 C 0.3479(2) 0.48766(16) 0.10171(9) 0.0333(4) Uani 1 1 d . . . . .
H7 H 0.402237 0.443982 0.137022 0.040 Uiso 1 1 calc R U . . .
C8 C 0.18295(18) 0.98410(13) 0.24012(8) 0.0233(3) Uani 1 1 d . . . . .
C9 C 0.20663(19) 1.04753(14) 0.17939(9) 0.0276(4) Uani 1 1 d . . . . .
C10 C 0.2295(2) 1.16592(15) 0.18093(10) 0.0378(5) Uani 1 1 d . . . . .
H10 H 0.247879 1.207971 0.141522 0.045 Uiso 1 1 calc R U . . .
C11 C 0.2257(2) 1.22183(16) 0.23902(11) 0.0418(5) Uani 1 1 d . . . . .
H11 H 0.246013 1.299350 0.238842 0.050 Uiso 1 1 calc R U . . .
C12 C 0.1918(2) 1.16274(15) 0.29754(10) 0.0360(4) Uani 1 1 d . . . . .
H12 H 0.185507 1.202134 0.336424 0.043 Uiso 1 1 calc R U . . .
C13 C 0.16668(19) 1.04518(14) 0.29945(9) 0.0265(4) Uani 1 1 d . . . . .
C14 C 0.1918(2) 0.99770(16) 0.11276(9) 0.0352(4) Uani 1 1 d . . . . .
H14 H 0.245036 0.914247 0.115330 0.042 Uiso 1 1 calc R U . . .
C15 C 0.2607(3) 1.06392(19) 0.05443(11) 0.0554(6) Uani 1 1 d . . . . .
H15A H 0.196820 1.140760 0.045166 0.083 Uiso 1 1 calc R U . . .
H15B H 0.264994 1.018108 0.016233 0.083 Uiso 1 1 calc R U . . .
H15C H 0.363635 1.074361 0.065366 0.083 Uiso 1 1 calc R U . . .
C16 C 0.0194(2) 0.99905(19) 0.09947(11) 0.0481(5) Uani 1 1 d . . . . .
H16A H -0.023805 0.955854 0.135314 0.072 Uiso 1 1 calc R U . . .
H16B H 0.008942 0.961926 0.059084 0.072 Uiso 1 1 calc R U . . .
H16C H -0.034858 1.080214 0.095687 0.072 Uiso 1 1 calc R U . . .
C17 C 0.1113(2) 0.98966(15) 0.36421(9) 0.0307(4) Uani 1 1 d . . . . .
H17 H 0.161082 0.905346 0.368205 0.037 Uiso 1 1 calc R U . . .
C18 C 0.1515(3) 1.04752(18) 0.42642(10) 0.0480(5) Uani 1 1 d . . . . .
H18A H 0.258098 1.057708 0.424292 0.072 Uiso 1 1 calc R U . . .
H18B H 0.135770 0.996928 0.464845 0.072 Uiso 1 1 calc R U . . .
H18C H 0.085798 1.124078 0.428987 0.072 Uiso 1 1 calc R U . . .
C19 C -0.0647(2) 0.99389(18) 0.36285(11) 0.0438(5) Uani 1 1 d . . . . .
H19A H -0.116772 1.075653 0.360958 0.066 Uiso 1 1 calc R U . . .
H19B H -0.096162 0.952189 0.402060 0.066 Uiso 1 1 calc R U . . .
H19C H -0.091351 0.956460 0.324673 0.066 Uiso 1 1 calc R U . . .
C20 C 0.30583(17) 0.68288(13) 0.38579(7) 0.0187(3) Uani 1 1 d . . . . .
C21 C 0.38934(18) 0.71094(14) 0.44048(8) 0.0247(4) Uani 1 1 d . . . . .
C22 C 0.3242(2) 0.70349(17) 0.50324(9) 0.0354(4) Uani 1 1 d . . . . .
H22 H 0.376336 0.724522 0.539011 0.043 Uiso 1 1 calc R U . . .
C23 C 0.1844(2) 0.66576(18) 0.51363(9) 0.0379(4) Uani 1 1 d . . . . .
H23 H 0.140477 0.664768 0.555654 0.046 Uiso 1 1 calc R U . . .
C24 C 0.1099(2) 0.62952(15) 0.46152(8) 0.0294(4) Uani 1 1 d . . . . .
H24 H 0.018805 0.599308 0.469390 0.035 Uiso 1 1 calc R U . . .
C25 C 0.16740(18) 0.63684(13) 0.39708(8) 0.0210(3) Uani 1 1 d . . . . .
C26 C 0.5489(2) 0.74756(17) 0.43354(9) 0.0340(4) Uani 1 1 d . . . . .
H26 H 0.597770 0.713665 0.393674 0.041 Uiso 1 1 calc R U . . .
C27 C 0.5375(2) 0.8825(2) 0.42468(13) 0.0551(6) Uani 1 1 d . . . . .
H27A H 0.478886 0.912445 0.385617 0.083 Uiso 1 1 calc R U . . .
H27B H 0.639906 0.901699 0.420428 0.083 Uiso 1 1 calc R U . . .
H27C H 0.486669 0.918681 0.462415 0.083 Uiso 1 1 calc R U . . .
C28 C 0.6553(2) 0.6978(2) 0.49199(11) 0.0595(7) Uani 1 1 d . . . . .
H28A H 0.614819 0.734442 0.531314 0.089 Uiso 1 1 calc R U . . .
H28B H 0.757553 0.714875 0.483189 0.089 Uiso 1 1 calc R U . . .
H28C H 0.660343 0.612778 0.498042 0.089 Uiso 1 1 calc R U . . .
C29 C 0.08067(18) 0.58598(13) 0.34443(8) 0.0219(3) Uani 1 1 d . . . . .
H29 H 0.119572 0.611409 0.301182 0.026 Uiso 1 1 calc R U . . .
C30 C 0.1177(2) 0.44961(14) 0.35200(9) 0.0314(4) Uani 1 1 d . . . . .
H30A H 0.227417 0.423405 0.346825 0.047 Uiso 1 1 calc R U . . .
H30B H 0.063235 0.417118 0.318896 0.047 Uiso 1 1 calc R U . . .
H30C H 0.085888 0.422525 0.395058 0.047 Uiso 1 1 calc R U . . .
C31 C -0.09438(19) 0.62947(16) 0.34566(9) 0.0312(4) Uani 1 1 d . . . . .
H31A H -0.137097 0.598284 0.385635 0.047 Uiso 1 1 calc R U . . .
H31B H -0.140673 0.602196 0.308279 0.047 Uiso 1 1 calc R U . . .
H31C H -0.115567 0.715298 0.343828 0.047 Uiso 1 1 calc R U . . .
C32 C 0.60401(17) 0.56123(14) 0.20960(8) 0.0205(3) Uani 1 1 d . . . . .
C33 C 0.67852(18) 0.65480(14) 0.18366(8) 0.0245(4) Uani 1 1 d . . . . .
C34 C 0.8358(2) 0.62872(17) 0.16715(9) 0.0323(4) Uani 1 1 d . . . . .
H34 H 0.886028 0.690047 0.150576 0.039 Uiso 1 1 calc R U . . .
C35 C 0.9180(2) 0.51355(18) 0.17499(10) 0.0383(5) Uani 1 1 d . . . . .
H35 H 1.023056 0.498018 0.164373 0.046 Uiso 1 1 calc R U . . .
C36 C 0.8445(2) 0.42158(17) 0.19855(9) 0.0337(4) Uani 1 1 d . . . . .
H36 H 0.900414 0.343998 0.202561 0.040 Uiso 1 1 calc R U . . .
C37 C 0.68862(19) 0.44226(14) 0.21644(8) 0.0245(4) Uani 1 1 d . . . . .
C38 C 0.6168(2) 0.33686(14) 0.24426(9) 0.0306(4) Uani 1 1 d . . . . .
H38 H 0.504505 0.358252 0.237405 0.037 Uiso 1 1 calc R U . . .
C39 C 0.6724(3) 0.22113(18) 0.21032(13) 0.0592(7) Uani 1 1 d . . . . .
H39A H 0.656482 0.235517 0.163538 0.089 Uiso 1 1 calc R U . . .
H39B H 0.614708 0.161097 0.227068 0.089 Uiso 1 1 calc R U . . .
H39C H 0.780829 0.194060 0.219012 0.089 Uiso 1 1 calc R U . . .
C40 C 0.6438(3) 0.3172(2) 0.31876(11) 0.0573(6) Uani 1 1 d . . . . .
H40A H 0.753277 0.299318 0.327386 0.086 Uiso 1 1 calc R U . . .
H40B H 0.596153 0.251671 0.335923 0.086 Uiso 1 1 calc R U . . .
H40C H 0.598903 0.388374 0.339752 0.086 Uiso 1 1 calc R U . . .
C41 C 0.5970(2) 0.78360(15) 0.17006(9) 0.0307(4) Uani 1 1 d . . . . .
H41 H 0.488713 0.788409 0.184396 0.037 Uiso 1 1 calc R U . . .
C42 C 0.6689(3) 0.87068(18) 0.20914(13) 0.0528(6) Uani 1 1 d . . . . .
H42A H 0.664631 0.848047 0.255503 0.079 Uiso 1 1 calc R U . . .
H42B H 0.611985 0.950304 0.200585 0.079 Uiso 1 1 calc R U . . .
H42C H 0.775060 0.868209 0.195808 0.079 Uiso 1 1 calc R U . . .
C43 C 0.5968(3) 0.8168(2) 0.09571(11) 0.0549(6) Uani 1 1 d . . . . .
H43A H 0.701757 0.806658 0.079658 0.082 Uiso 1 1 calc R U . . .
H43B H 0.547747 0.898737 0.087344 0.082 Uiso 1 1 calc R U . . .
H43C H 0.540802 0.765982 0.073459 0.082 Uiso 1 1 calc R U . . .
N1 N 0.18340(15) 0.76152(11) 0.18064(7) 0.0222(3) Uani 1 1 d . . . . .
P1 P 0.15720(5) 0.82519(3) 0.25413(2) 0.01973(10) Uani 1 1 d . . . . .
P2 P 0.38086(5) 0.73301(3) 0.30442(2) 0.01906(10) Uani 1 1 d . . . . .
P3 P 0.40142(5) 0.58143(3) 0.24144(2) 0.01890(10) 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'
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 C2 118.73(14) . . ?
N1 C1 P3 122.45(12) . . ?
C2 C1 P3 118.58(11) . . ?
C3 C2 C7 118.30(16) . . ?
C3 C2 C1 119.81(15) . . ?
C7 C2 C1 121.88(15) . . ?
C4 C3 C2 120.65(19) . . ?
C5 C4 C3 120.4(2) . . ?
C6 C5 C4 119.68(19) . . ?
C5 C6 C7 120.31(19) . . ?
C6 C7 C2 120.67(18) . . ?
C9 C8 C13 119.60(14) . . ?
C9 C8 P1 128.02(13) . . ?
C13 C8 P1 112.27(12) . . ?
C10 C9 C8 118.15(16) . . ?
C10 C9 C14 118.52(16) . . ?
C8 C9 C14 123.02(15) . . ?
C11 C10 C9 121.89(17) . . ?
C10 C11 C12 119.86(16) . . ?
C11 C12 C13 121.15(18) . . ?
C12 C13 C8 118.93(16) . . ?
C12 C13 C17 118.50(16) . . ?
C8 C13 C17 122.41(14) . . ?
C9 C14 C15 114.98(17) . . ?
C9 C14 C16 108.63(15) . . ?
C15 C14 C16 109.10(17) . . ?
C13 C17 C19 110.53(15) . . ?
C13 C17 C18 114.64(15) . . ?
C19 C17 C18 108.52(16) . . ?
C25 C20 C21 119.44(14) . . ?
C25 C20 P2 126.33(12) . . ?
C21 C20 P2 113.63(12) . . ?
C22 C21 C20 118.77(15) . . ?
C22 C21 C26 118.32(15) . . ?
C20 C21 C26 122.90(15) . . ?
C23 C22 C21 121.51(16) . . ?
C24 C23 C22 119.58(17) . . ?
C23 C24 C25 121.77(16) . . ?
C24 C25 C20 118.57(14) . . ?
C24 C25 C29 116.76(14) . . ?
C20 C25 C29 124.53(14) . . ?
C27 C26 C21 112.12(15) . . ?
C27 C26 C28 109.72(17) . . ?
C21 C26 C28 112.32(17) . . ?
C25 C29 C31 113.55(13) . . ?
C25 C29 C30 109.18(13) . . ?
C31 C29 C30 110.50(13) . . ?
C33 C32 C37 119.67(14) . . ?
C33 C32 P3 124.80(12) . . ?
C37 C32 P3 115.42(12) . . ?
C34 C33 C32 118.92(15) . . ?
C34 C33 C41 116.92(15) . . ?
C32 C33 C41 124.12(14) . . ?
C35 C34 C33 121.15(17) . . ?
C36 C35 C34 120.03(17) . . ?
C35 C36 C37 121.40(16) . . ?
C36 C37 C32 118.78(16) . . ?
C36 C37 C38 118.41(15) . . ?
C32 C37 C38 122.79(14) . . ?
C37 C38 C39 114.02(16) . . ?
C37 C38 C40 110.18(15) . . ?
C39 C38 C40 110.63(17) . . ?
C33 C41 C43 109.62(15) . . ?
C33 C41 C42 111.96(16) . . ?
C43 C41 C42 111.95(17) . . ?
C1 N1 P1 122.95(11) . . ?
N1 P1 C8 107.81(7) . . ?
N1 P1 P2 98.79(5) . . ?
C8 P1 P2 103.97(5) . . ?
C20 P2 P3 106.94(5) . . ?
C20 P2 P1 100.97(5) . . ?
P3 P2 P1 91.91(2) . . ?
C32 P3 C1 106.23(7) . . ?
C32 P3 P2 104.97(5) . . ?
C1 P3 P2 96.14(5) . . ?
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 1.2821(19) . ?
C1 C2 1.498(2) . ?
C1 P3 1.8697(16) . ?
C2 C3 1.391(3) . ?
C2 C7 1.394(2) . ?
C3 C4 1.384(3) . ?
C4 C5 1.379(3) . ?
C5 C6 1.375(3) . ?
C6 C7 1.385(3) . ?
C8 C9 1.416(2) . ?
C8 C13 1.424(2) . ?
C8 P1 1.8640(15) . ?
C9 C10 1.399(2) . ?
C9 C14 1.517(3) . ?
C10 C11 1.374(3) . ?
C11 C12 1.379(3) . ?
C12 C13 1.391(2) . ?
C13 C17 1.528(2) . ?
C14 C15 1.533(3) . ?
C14 C16 1.534(3) . ?
C17 C19 1.533(3) . ?
C17 C18 1.536(3) . ?
C20 C25 1.412(2) . ?
C20 C21 1.422(2) . ?
C20 P2 1.8579(16) . ?
C21 C22 1.391(2) . ?
C21 C26 1.528(2) . ?
C22 C23 1.375(3) . ?
C23 C24 1.374(2) . ?
C24 C25 1.396(2) . ?
C25 C29 1.522(2) . ?
C26 C27 1.520(3) . ?
C26 C28 1.533(3) . ?
C29 C31 1.525(2) . ?
C29 C30 1.526(2) . ?
C32 C33 1.412(2) . ?
C32 C37 1.423(2) . ?
C32 P3 1.8588(16) . ?
C33 C34 1.397(2) . ?
C33 C41 1.522(2) . ?
C34 C35 1.380(3) . ?
C35 C36 1.377(3) . ?
C36 C37 1.390(2) . ?
C37 C38 1.521(2) . ?
C38 C39 1.528(2) . ?
C38 C40 1.529(3) . ?
C41 C43 1.530(3) . ?
C41 C42 1.533(3) . ?
N1 P1 1.6970(14) . ?
P1 P2 2.2724(6) . ?
P2 P3 2.1972(5) . ?
