#------------------------------------------------------------------------------
#$Date: 2023-09-05 22:05:20 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286028 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/93/1569382.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_1569382
loop_
_publ_author_name
'Löwe, Pawel'
'Wünsche, Marius A'
'Purtscher, Felix R. S.'
'Gamper, Jakob'
'Hofer, Thomas S.'
'Wilm, Lukas F. B.'
'Röthel, Maike B'
'Dielmann, Fabian'
_publ_section_title
;
 Terminal methylene phosphonium ions: precursors for transient
 monosubstituted phosphinocarbenes.
;
_journal_issue                   29
_journal_name_full               'Chemical science'
_journal_page_first              7928
_journal_page_last               7935
_journal_paper_doi               10.1039/d3sc02899b
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C23 H47 N6 P'
_chemical_formula_sum            'C23 H47 N6 P'
_chemical_formula_weight         438.63
_chemical_name_systematic        (sItBuN)2PMe
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-02-23 deposited with the CCDC.	2023-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.6430(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9856(3)
_cell_length_b                   9.8313(2)
_cell_length_c                   20.5049(5)
_cell_measurement_reflns_used    9696
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.57
_cell_measurement_theta_min      2.31
_cell_volume                     2563.90(10)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_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  0.0326
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            41012
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.574
_diffrn_reflns_theta_min         2.028
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1262 before and 0.0550 after correction.
The Ratio of minimum to maximum transmission is 0.8442.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_preparation       'via EXP PL790'
_exptl_crystal_recrystallization_method
'crystallized out of a concentrated n-hexane solution at room temperature'
_exptl_crystal_size_max          0.742
_exptl_crystal_size_mid          0.589
_exptl_crystal_size_min          0.442
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         7191
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0557P)²+0.6406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1026
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6885
_reflns_number_total             7191
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc02899b2.cif
_cod_data_source_block           p21c_a
_cod_depositor_comments
'Adding full bibliography for 1569380--1569388.cif.'
_cod_database_code               1569382
_shelxl_version_number           2013-4
_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_max   0.946
_shelx_estimated_absorpt_t_min   0.911
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Others
 Sof(H1BD)=Sof(H1BE)=Sof(H1BF)=Sof(P1B)=1-FVAR(1)
 Sof(P1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C3(H3A,H3B), C7(H7A,H7B), C6(H6A,H6B)
3.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C23(H23A,H23B,H23C), C14(H14A,H14B,H14C), C11(H11A,H11B,
 H11C), C13(H13A,H13B,H13C), C18(H18A,H18B,H18C), C15(H15A,H15B,H15C), C21(H21A,
 H21B,H21C), C19(H19A,H19B,H19C), C17(H17A,H17B,H17C), C9(H9A,H9B,H9C),
 C22(H22A,H22B,H22C), C1(H1AA,H1AB,H1AC), C1(H1BD,H1BE,H1BF)
;
_olex2_exptl_crystal_mounting_method 'mounted on glass capillary'
_olex2_submission_original_sample_id PL790
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
P1A P 0.70743(2) 0.16114(2) 0.35477(2) 0.01048(8) Uani 0.9567(12) 1 d . . P A 1
N5 N 0.53863(5) 0.43932(7) 0.32244(4) 0.01289(14) Uani 1 1 d . . . . .
N2 N 0.99223(5) 0.15391(7) 0.39236(3) 0.01185(14) Uani 1 1 d . . . . .
N6 N 0.47403(5) 0.36432(7) 0.41023(4) 0.01231(13) Uani 1 1 d . . . . .
N3 N 0.96721(5) 0.26504(7) 0.48489(3) 0.01227(13) Uani 1 1 d . . . . .
N4 N 0.61603(6) 0.24165(7) 0.38812(4) 0.01396(14) Uani 1 1 d . . . . .
N1 N 0.81510(6) 0.19545(8) 0.41215(4) 0.01443(14) Uani 1 1 d . . . . .
C5 C 0.55182(6) 0.34086(8) 0.37272(4) 0.01118(15) Uani 1 1 d . . . . .
C2 C 0.91454(6) 0.20321(8) 0.42564(4) 0.01068(14) Uani 1 1 d . . . . .
C8 C 0.97587(7) 0.14520(9) 0.31829(4) 0.01313(15) Uani 1 1 d . . . . .
C4 C 1.07585(6) 0.21747(9) 0.49855(4) 0.01505(16) Uani 1 1 d . . . . .
H4A H 1.0833 0.1294 0.5224 0.018 Uiso 1 1 calc R U . . .
H4B H 1.1240 0.2850 0.5245 0.018 Uiso 1 1 calc R U . . .
C10 C 0.90658(7) 0.02264(9) 0.29277(4) 0.01682(16) Uani 1 1 d . . . . .
H10A H 0.9388 -0.0604 0.3142 0.025 Uiso 1 1 calc R U . . .
H10B H 0.8997 0.0149 0.2444 0.025 Uiso 1 1 calc R U . . .
H10C H 0.8368 0.0349 0.3033 0.025 Uiso 1 1 calc R U . . .
C23 C 0.36361(7) 0.32878(9) 0.49186(5) 0.01851(17) Uani 1 1 d . . . . .
H23A H 0.3882 0.4174 0.5107 0.028 Uiso 1 1 calc R U . . .
H23B H 0.3499 0.2690 0.5274 0.028 Uiso 1 1 calc R U . . .
H23C H 0.2988 0.3409 0.4584 0.028 Uiso 1 1 calc R U . . .
C14 C 0.86914(7) 0.16337(9) 0.56573(4) 0.01762(17) Uani 1 1 d . . . . .
H14A H 0.8145 0.1259 0.5303 0.026 Uiso 1 1 calc R U . . .
H14B H 0.8388 0.1844 0.6046 0.026 Uiso 1 1 calc R U . . .
H14C H 0.9257 0.0966 0.5782 0.026 Uiso 1 1 calc R U . . .
C11 C 0.92772(7) 0.27745(9) 0.28626(5) 0.01856(17) Uani 1 1 d . . . . .
H11A H 0.8566 0.2882 0.2948 0.028 Uiso 1 1 calc R U . . .
H11B H 0.9245 0.2740 0.2381 0.028 Uiso 1 1 calc R U . . .
H11C H 0.9712 0.3547 0.3054 0.028 Uiso 1 1 calc R U . . .
C13 C 0.99479(8) 0.35630(10) 0.59774(4) 0.01976(18) Uani 1 1 d . . . . .
H13A H 1.0497 0.2893 0.6143 0.030 Uiso 1 1 calc R U . . .
H13B H 0.9601 0.3833 0.6340 0.030 Uiso 1 1 calc R U . . .
H13C H 1.0264 0.4364 0.5812 0.030 Uiso 1 1 calc R U . . .
C18 C 0.72653(7) 0.51162(9) 0.34126(4) 0.01611(16) Uani 1 1 d . . . . .
H18A H 0.7150 0.5731 0.3767 0.024 Uiso 1 1 calc R U . . .
H18B H 0.7804 0.5500 0.3193 0.024 Uiso 1 1 calc R U . . .
H18C H 0.7501 0.4229 0.3605 0.024 Uiso 1 1 calc R U . . .
C20 C 0.44815(6) 0.26467(8) 0.45905(4) 0.01353(15) Uani 1 1 d . . . . .
C12 C 0.91357(6) 0.29351(8) 0.54102(4) 0.01276(15) Uani 1 1 d . . . . .
C3 C 1.09436(6) 0.20302(9) 0.42848(4) 0.01499(16) Uani 1 1 d . . . . .
H3A H 1.1127 0.2914 0.4107 0.018 Uiso 1 1 calc R U . . .
H3B H 1.1508 0.1365 0.4264 0.018 Uiso 1 1 calc R U . . .
C16 C 0.62352(6) 0.49418(9) 0.29012(4) 0.01328(15) Uani 1 1 d . . . . .
C7 C 0.38979(7) 0.44227(9) 0.36903(4) 0.01662(16) Uani 1 1 d . . . . .
H7A H 0.3518 0.4988 0.3965 0.020 Uiso 1 1 calc R U . . .
H7B H 0.3391 0.3823 0.3398 0.020 Uiso 1 1 calc R U . . .
C15 C 0.82646(7) 0.39893(9) 0.51991(4) 0.01723(17) Uani 1 1 d . . . . .
H15A H 0.8553 0.4787 0.5012 0.026 Uiso 1 1 calc R U . . .
H15B H 0.7982 0.4264 0.5588 0.026 Uiso 1 1 calc R U . . .
H15C H 0.7701 0.3592 0.4863 0.026 Uiso 1 1 calc R U . . .
C21 C 0.54444(7) 0.23891(10) 0.51455(4) 0.01896(17) Uani 1 1 d . . . . .
H21A H 0.5980 0.1900 0.4963 0.028 Uiso 1 1 calc R U . . .
H21B H 0.5237 0.1842 0.5497 0.028 Uiso 1 1 calc R U . . .
H21C H 0.5732 0.3261 0.5331 0.028 Uiso 1 1 calc R U . . .
C6 C 0.45104(7) 0.52891(9) 0.32926(5) 0.01815(17) Uani 1 1 d . . . . .
H6A H 0.4079 0.5528 0.2852 0.022 Uiso 1 1 calc R U . . .
H6B H 0.4767 0.6134 0.3534 0.022 Uiso 1 1 calc R U . . .
C19 C 0.59202(8) 0.63615(10) 0.26112(5) 0.02044(18) Uani 1 1 d . . . . .
H19A H 0.5254 0.6298 0.2288 0.031 Uiso 1 1 calc R U . . .
H19B H 0.6468 0.6708 0.2389 0.031 Uiso 1 1 calc R U . . .
H19C H 0.5838 0.6981 0.2971 0.031 Uiso 1 1 calc R U . . .
C17 C 0.63613(7) 0.40262(9) 0.23185(4) 0.01766(17) Uani 1 1 d . . . . .
H17A H 0.6549 0.3105 0.2483 0.026 Uiso 1 1 calc R U . . .
H17B H 0.6918 0.4389 0.2108 0.026 Uiso 1 1 calc R U . . .
H17C H 0.5698 0.3998 0.1991 0.026 Uiso 1 1 calc R U . . .
C9 C 1.08271(7) 0.12271(10) 0.29858(5) 0.01875(17) Uani 1 1 d . . . . .
H9A H 1.1274 0.2026 0.3112 0.028 Uiso 1 1 calc R U . . .
H9B H 1.0720 0.1090 0.2503 0.028 Uiso 1 1 calc R U . . .
H9C H 1.1168 0.0422 0.3216 0.028 Uiso 1 1 calc R U . . .
C22 C 0.40634(8) 0.13134(9) 0.42508(5) 0.01954(18) Uani 1 1 d . . . . .
H22A H 0.3443 0.1502 0.3903 0.029 Uiso 1 1 calc R U . . .
H22B H 0.3871 0.0694 0.4581 0.029 Uiso 1 1 calc R U . . .
H22C H 0.4609 0.0891 0.4051 0.029 Uiso 1 1 calc R U . . .
C1 C 0.68275(7) -0.01155(9) 0.38325(5) 0.02052(18) Uani 1 1 d . . . . .
H1AA H 0.6847 -0.0100 0.4313 0.031 Uiso 0.9567(12) 1 calc R U P A 1
H1AB H 0.7370 -0.0736 0.3738 0.031 Uiso 0.9567(12) 1 calc R U P A 1
H1AC H 0.6135 -0.0427 0.3598 0.031 Uiso 0.9567(12) 1 calc R U P A 1
H1BD H 0.6179 -0.0515 0.3922 0.031 Uiso 0.0433(12) 1 calc R U P A 2
H1BE H 0.7420 -0.0721 0.4002 0.031 Uiso 0.0433(12) 1 calc R U P A 2
H1BF H 0.6762 0.0005 0.3351 0.031 Uiso 0.0433(12) 1 calc R U P A 2
P1B P 0.7028(5) 0.1345(7) 0.4199(4) 0.0285(18) Uani 0.0433(12) 1 d . . P A 2
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
N4 P1A C1 97.03(4) . . ?
N1 P1A N4 100.23(4) . . ?
N1 P1A C1 97.88(4) . . ?
C5 N5 C16 125.73(7) . . ?
C5 N5 C6 109.09(7) . . ?
C6 N5 C16 118.70(7) . . ?
C2 N2 C8 122.82(7) . . ?
C2 N2 C3 107.75(6) . . ?
C3 N2 C8 117.50(7) . . ?
C5 N6 C20 123.02(7) . . ?
C5 N6 C7 107.88(7) . . ?
C7 N6 C20 119.43(7) . . ?
C2 N3 C4 108.07(6) . . ?
C2 N3 C12 121.86(7) . . ?
C4 N3 C12 119.84(7) . . ?
C5 N4 P1A 137.37(7) . . ?
C5 N4 P1B 169.1(3) . . ?
C2 N1 P1A 146.86(7) . . ?
C2 N1 P1B 154.5(2) . . ?
N5 C5 N6 107.14(7) . . ?
N4 C5 N5 133.27(8) . . ?
N4 C5 N6 119.58(7) . . ?
N3 C2 N2 107.18(7) . . ?
N1 C2 N2 132.03(8) . . ?
N1 C2 N3 120.73(7) . . ?
N2 C8 C10 110.23(7) . . ?
N2 C8 C11 110.45(7) . . ?
N2 C8 C9 108.96(7) . . ?
C10 C8 C11 111.13(7) . . ?
C10 C8 C9 107.24(7) . . ?
C11 C8 C9 108.74(7) . . ?
N3 C4 H4A 111.7 . . ?
N3 C4 H4B 111.7 . . ?
N3 C4 C3 100.42(6) . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4A 111.7 . . ?
C3 C4 H4B 111.7 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
N6 C20 C23 107.67(7) . . ?
N6 C20 C21 110.33(7) . . ?
N6 C20 C22 111.42(7) . . ?
C21 C20 C23 106.92(7) . . ?
C22 C20 C23 109.38(7) . . ?
C22 C20 C21 110.95(7) . . ?
N3 C12 C14 111.44(7) . . ?
N3 C12 C13 107.75(7) . . ?
N3 C12 C15 110.08(7) . . ?
C14 C12 C13 109.44(7) . . ?
C15 C12 C14 110.67(7) . . ?
C15 C12 C13 107.32(7) . . ?
N2 C3 C4 102.14(6) . . ?
N2 C3 H3A 111.3 . . ?
N2 C3 H3B 111.3 . . ?
C4 C3 H3A 111.3 . . ?
C4 C3 H3B 111.3 . . ?
H3A C3 H3B 109.2 . . ?
N5 C16 C18 110.87(6) . . ?
N5 C16 C19 109.62(7) . . ?
N5 C16 C17 109.76(7) . . ?
C18 C16 C19 106.84(7) . . ?
C17 C16 C18 112.55(7) . . ?
C17 C16 C19 107.06(7) . . ?
N6 C7 H7A 111.5 . . ?
N6 C7 H7B 111.5 . . ?
N6 C7 C6 101.18(7) . . ?
H7A C7 H7B 109.4 . . ?
C6 C7 H7A 111.5 . . ?
C6 C7 H7B 111.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N5 C6 C7 102.44(7) . . ?
N5 C6 H6A 111.3 . . ?
N5 C6 H6B 111.3 . . ?
C7 C6 H6A 111.3 . . ?
C7 C6 H6B 111.3 . . ?
H6A C6 H6B 109.2 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
P1A C1 H1AA 109.5 . . ?
P1A C1 H1AB 109.5 . . ?
P1A C1 H1AC 109.5 . . ?
H1AA C1 H1AB 109.5 . . ?
H1AA C1 H1AC 109.5 . . ?
H1AB C1 H1AC 109.5 . . ?
H1BD C1 H1BE 109.5 . . ?
H1BD C1 H1BF 109.5 . . ?
H1BE C1 H1BF 109.5 . . ?
P1B C1 H1BD 109.5 . . ?
P1B C1 H1BE 109.5 . . ?
P1B C1 H1BF 109.5 . . ?
N4 P1B N1 107.2(4) . . ?
N4 P1B C1 111.4(4) . . ?
N1 P1B C1 110.4(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
P1A N4 1.6824(8) . ?
P1A N1 1.6700(8) . ?
P1A C1 1.8444(9) . ?
N5 C5 1.3992(10) . ?
N5 C16 1.4967(10) . ?
N5 C6 1.4674(11) . ?
N2 C2 1.4128(10) . ?
N2 C8 1.4932(11) . ?
N2 C3 1.4642(10) . ?
N6 C5 1.4066(10) . ?
N6 C20 1.4869(11) . ?
N6 C7 1.4575(10) . ?
N3 C2 1.4065(10) . ?
N3 C4 1.4588(10) . ?
N3 C12 1.4871(10) . ?
N4 C5 1.2806(10) . ?
N4 P1B 1.583(7) . ?
N1 C2 1.2672(10) . ?
N1 P1B 1.613(7) . ?
C8 C10 1.5314(12) . ?
C8 C11 1.5320(12) . ?
C8 C9 1.5372(12) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.5106(12) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C23 C20 1.5340(11) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C14 C12 1.5313(12) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 C12 1.5334(12) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 C16 1.5337(12) . ?
C20 C21 1.5324(12) . ?
C20 C22 1.5315(12) . ?
C12 C15 1.5309(12) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C16 C19 1.5398(12) . ?
C16 C17 1.5309(12) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C6 1.5116(13) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C1 H1AA 0.9800 . ?
C1 H1AB 0.9800 . ?
C1 H1AC 0.9800 . ?
C1 H1BD 0.9800 . ?
C1 H1BE 0.9800 . ?
C1 H1BF 0.9800 . ?
C1 P1B 1.617(8) . ?
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
P1A N4 C5 N5 -9.25(16) . . . . ?
P1A N4 C5 N6 169.72(7) . . . . ?
P1A N4 P1B N1 56.7(3) . . . . ?
P1A N4 P1B C1 -64.1(4) . . . . ?
P1A N1 C2 N2 -15.01(19) . . . . ?
P1A N1 C2 N3 168.23(9) . . . . ?
P1A N1 P1B N4 -57.6(3) . . . . ?
P1A N1 P1B C1 63.9(3) . . . . ?
P1A C1 P1B N4 60.1(3) . . . . ?
P1A C1 P1B N1 -58.8(3) . . . . ?
N6 C7 C6 N5 32.54(8) . . . . ?
N3 C4 C3 N2 -36.63(8) . . . . ?
N4 P1A N1 C2 -160.05(12) . . . . ?
N4 P1A N1 P1B 50.5(3) . . . . ?
N4 P1A C1 P1B -49.9(3) . . . . ?
N1 P1A N4 C5 116.75(9) . . . . ?
N1 P1A N4 P1B -51.6(3) . . . . ?
N1 P1A C1 P1B 51.5(3) . . . . ?
C5 N5 C16 C18 -38.38(11) . . . . ?
C5 N5 C16 C19 -156.10(8) . . . . ?
C5 N5 C16 C17 86.58(9) . . . . ?
C5 N5 C6 C7 -21.56(9) . . . . ?
C5 N6 C20 C23 177.55(7) . . . . ?
C5 N6 C20 C21 61.21(10) . . . . ?
C5 N6 C20 C22 -62.51(10) . . . . ?
C5 N6 C7 C6 -33.76(9) . . . . ?
C5 N4 P1B N1 -77.1(15) . . . . ?
C5 N4 P1B C1 162.1(10) . . . . ?
C2 N2 C8 C10 -76.79(9) . . . . ?
C2 N2 C8 C11 46.40(10) . . . . ?
C2 N2 C8 C9 165.79(7) . . . . ?
C2 N2 C3 C4 28.02(8) . . . . ?
C2 N3 C4 C3 33.97(8) . . . . ?
C2 N3 C12 C14 58.06(10) . . . . ?
C2 N3 C12 C13 178.14(7) . . . . ?
C2 N3 C12 C15 -65.12(10) . . . . ?
C2 N1 P1B N4 162.5(3) . . . . ?
C2 N1 P1B C1 -76.0(8) . . . . ?
C8 N2 C2 N3 -148.98(7) . . . . ?
C8 N2 C2 N1 33.92(13) . . . . ?
C8 N2 C3 C4 171.96(7) . . . . ?
C4 N3 C2 N2 -17.55(9) . . . . ?
C4 N3 C2 N1 159.94(8) . . . . ?
C4 N3 C12 C14 -82.96(9) . . . . ?
C4 N3 C12 C13 37.11(10) . . . . ?
C4 N3 C12 C15 153.85(7) . . . . ?
C20 N6 C5 N5 166.96(7) . . . . ?
C20 N6 C5 N4 -12.26(12) . . . . ?
C20 N6 C7 C6 179.15(7) . . . . ?
C12 N3 C2 N2 -162.53(7) . . . . ?
C12 N3 C2 N1 14.96(12) . . . . ?
C12 N3 C4 C3 179.78(7) . . . . ?
C3 N2 C2 N3 -7.40(9) . . . . ?
C3 N2 C2 N1 175.51(9) . . . . ?
C3 N2 C8 C10 145.07(7) . . . . ?
C3 N2 C8 C11 -91.74(9) . . . . ?
C3 N2 C8 C9 27.64(10) . . . . ?
C16 N5 C5 N6 152.05(7) . . . . ?
C16 N5 C5 N4 -28.89(14) . . . . ?
C16 N5 C6 C7 -174.92(7) . . . . ?
C7 N6 C5 N5 21.31(9) . . . . ?
C7 N6 C5 N4 -157.91(8) . . . . ?
C7 N6 C20 C23 -40.52(10) . . . . ?
C7 N6 C20 C21 -156.86(7) . . . . ?
C7 N6 C20 C22 79.42(9) . . . . ?
C6 N5 C5 N6 1.02(9) . . . . ?
C6 N5 C5 N4 -179.91(9) . . . . ?
C6 N5 C16 C18 110.16(8) . . . . ?
C6 N5 C16 C19 -7.55(10) . . . . ?
C6 N5 C16 C17 -124.88(8) . . . . ?
C1 P1A N4 C5 -143.89(9) . . . . ?
C1 P1A N4 P1B 47.8(3) . . . . ?
C1 P1A N1 C2 101.29(13) . . . . ?
C1 P1A N1 P1B -48.2(3) . . . . ?
P1B N4 C5 N5 116.4(13) . . . . ?
P1B N4 C5 N6 -64.6(14) . . . . ?
P1B N1 C2 N2 101.5(7) . . . . ?
P1B N1 C2 N3 -75.3(7) . . . . ?
