#------------------------------------------------------------------------------
#$Date: 2020-12-19 04:23:18 +0100 (Sat 19 de Dec de 2020) $
#$Revision: 259993 $
#$URL: svn://www.crystallography.net/cod/cif/7/70/61/7706117.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_7706117
loop_
_publ_author_name
'Cicač-Hudi, Mario'
'Feil, Christoph M.'
'Birchall, Nicholas'
'Nieger, Martin'
'Gudat, Dietrich'
_publ_section_title
;
 Proton transfer vs. oligophosphine formation by P-C/P-H σ-bond
 metathesis: decoding the competing Brønsted and Lewis type reactivities
 of imidazolio-phosphines.
;
_journal_issue                   47
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              17401
_journal_page_last               17413
_journal_paper_doi               10.1039/d0dt03633a
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C22 H28 N2 P, B F4'
_chemical_formula_sum            'C22 H28 B F4 N2 P'
_chemical_formula_weight         438.24
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-03-23 deposited with the CCDC.	2020-11-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.181(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.6034(5)
_cell_length_b                   27.3731(13)
_cell_length_c                   16.1467(7)
_cell_measurement_reflns_used    7252
_cell_measurement_temperature    135(2)
_cell_measurement_theta_max      28.334
_cell_measurement_theta_min      1.464
_cell_volume                     4685.6(4)
_computing_cell_refinement       'Bruker ApexII Software Suite, 2008'
_computing_data_collection       'Bruker ApexII Software Suite, 2008'
_computing_data_reduction        'Bruker ApexII Software Suite, 2008'
_computing_molecular_graphics    'SHELX plus XP (Sheldrick, 1991)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      135(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker Kappa ApexII Duo'
_diffrn_measurement_method       'Omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            41082
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.334
_diffrn_reflns_theta_min         1.464
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BLESSING 1995'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_description       plate
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.639
_exptl_crystal_size_mid          0.503
_exptl_crystal_size_min          0.194
_refine_diff_density_max         1.173
_refine_diff_density_min         -1.030
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     562
_refine_ls_number_reflns         11552
_refine_ls_number_restraints     721
_refine_ls_restrained_S_all      1.204
_refine_ls_R_factor_all          0.1427
_refine_ls_R_factor_gt           0.0944
_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)+(0.1130P)²+9.5711P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2370
_refine_ls_wR_factor_ref         0.2697
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7251
_reflns_number_total             11552
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt03633a2.cif
_cod_data_source_block           g579_mn_1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7706117
_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   0.905
_shelx_estimated_absorpt_t_max   0.970
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
C1A C 0.8030(7) 0.1294(3) 0.0362(4) 0.0626(16) Uiso 0.75 1 d D . P A 1
H1A1 H 0.7522 0.1515 0.0015 0.094 Uiso 0.75 1 calc R U P A 1
H1A2 H 0.8915 0.1397 0.0359 0.094 Uiso 0.75 1 calc R U P A 1
H1A3 H 0.7959 0.0960 0.0145 0.094 Uiso 0.75 1 calc R U P A 1
C1B C 0.737(2) 0.1076(7) 0.0384(7) 0.0626(16) Uiso 0.25 1 d D . P A 2
H1B1 H 0.6794 0.1279 0.0049 0.094 Uiso 0.25 1 calc R U P A 2
H1B2 H 0.8212 0.1082 0.0145 0.094 Uiso 0.25 1 calc R U P A 2
H1B3 H 0.7058 0.0739 0.0392 0.094 Uiso 0.25 1 calc R U P A 2
P1 P 0.74565(10) 0.13100(4) 0.14299(7) 0.0413(3) Uani 1 1 d D U . . .
H1PA H 0.650(2) 0.1045(12) 0.135(2) 0.050 Uiso 0.75 1 d D U P B 1
H1PB H 0.817(4) 0.1670(11) 0.135(3) 0.050 Uiso 0.25 1 d D U P C 2
C2 C 0.8562(3) 0.08742(12) 0.1901(2) 0.0296(7) Uani 1 1 d D U . . .
N1 N 0.9705(3) 0.09851(11) 0.22251(17) 0.0314(6) Uani 1 1 d . U . . .
N2 N 0.8372(3) 0.03970(11) 0.20548(18) 0.0330(6) Uani 1 1 d . U . . .
C3 C 1.0228(4) 0.05730(15) 0.2584(3) 0.0431(9) Uani 1 1 d . U . . .
H3 H 1.1031 0.0552 0.2854 0.052 Uiso 1 1 calc R U . . .
C4 C 0.9403(4) 0.02098(15) 0.2483(3) 0.0422(9) Uani 1 1 d . U . . .
H4 H 0.9506 -0.0117 0.2671 0.051 Uiso 1 1 calc R U . . .
C5 C 1.0276(3) 0.14619(13) 0.2235(2) 0.0314(7) Uani 1 1 d . U . . .
C6 C 1.1152(3) 0.15747(13) 0.1628(2) 0.0329(7) Uani 1 1 d . U . . .
C7 C 1.1739(4) 0.20253(14) 0.1687(2) 0.0385(8) Uani 1 1 d . U . . .
H7 H 1.2331 0.2115 0.1280 0.046 Uiso 1 1 calc R U . . .
C8 C 1.1490(4) 0.23498(14) 0.2323(2) 0.0405(9) Uani 1 1 d . U . . .
C9 C 1.0611(4) 0.22234(15) 0.2908(2) 0.0425(9) Uani 1 1 d . U . . .
H9 H 1.0425 0.2448 0.3337 0.051 Uiso 1 1 calc R U . . .
C10 C 0.9995(3) 0.17757(14) 0.2884(2) 0.0365(8) Uani 1 1 d . U . . .
C11 C 0.7230(4) 0.01315(13) 0.1849(2) 0.0379(8) Uani 1 1 d . U . . .
C12 C 0.6237(4) 0.01682(14) 0.2387(3) 0.0423(9) Uani 1 1 d . U . . .
C13 C 0.5129(4) -0.00786(16) 0.2170(4) 0.0593(12) Uani 1 1 d . U . . .
H13 H 0.4423 -0.0057 0.2521 0.071 Uiso 1 1 calc R U . . .
C14 C 0.5039(5) -0.03533(17) 0.1455(4) 0.0721(14) Uani 1 1 d . U . . .
C15 C 0.6057(6) -0.03848(18) 0.0949(4) 0.0724(14) Uani 1 1 d . U . . .
H15 H 0.5987 -0.0578 0.0461 0.087 Uiso 1 1 calc R U . . .
C16 C 0.7186(5) -0.01452(15) 0.1121(3) 0.0546(11) Uani 1 1 d . U . . .
C17 C 1.1484(4) 0.12188(16) 0.0958(2) 0.0460(10) Uani 1 1 d . U . . .
H17A H 1.1947 0.1389 0.0525 0.069 Uiso 1 1 calc R U . . .
H17B H 1.0709 0.1078 0.0718 0.069 Uiso 1 1 calc R U . . .
H17C H 1.2011 0.0958 0.1194 0.069 Uiso 1 1 calc R U . . .
C18 C 1.2205(5) 0.28274(16) 0.2400(3) 0.0582(12) Uani 1 1 d . U . . .
H18A H 1.3037 0.2767 0.2656 0.087 Uiso 1 1 calc R U . . .
H18B H 1.1733 0.3054 0.2747 0.087 Uiso 1 1 calc R U . . .
H18C H 1.2308 0.2970 0.1849 0.087 Uiso 1 1 calc R U . . .
C19 C 0.9080(4) 0.16301(18) 0.3542(3) 0.0516(11) Uani 1 1 d . U . . .
H19A H 0.8235 0.1594 0.3293 0.077 Uiso 1 1 calc R U . . .
H19B H 0.9063 0.1883 0.3972 0.077 Uiso 1 1 calc R U . . .
H19C H 0.9346 0.1319 0.3791 0.077 Uiso 1 1 calc R U . . .
C20 C 0.6336(4) 0.04644(16) 0.3169(3) 0.0482(10) Uani 1 1 d . U . . .
H20A H 0.7122 0.0382 0.3468 0.072 Uiso 1 1 calc R U . . .
H20B H 0.5616 0.0391 0.3519 0.072 Uiso 1 1 calc R U . . .
H20C H 0.6335 0.0813 0.3030 0.072 Uiso 1 1 calc R U . . .
C21 C 0.3814(7) -0.0615(2) 0.1246(6) 0.118(3) Uani 1 1 d . U . . .
H21A H 0.3709 -0.0891 0.1624 0.177 Uiso 1 1 calc R U . . .
H21B H 0.3833 -0.0734 0.0674 0.177 Uiso 1 1 calc R U . . .
H21C H 0.3106 -0.0388 0.1305 0.177 Uiso 1 1 calc R U . . .
C22 C 0.8293(6) -0.0187(2) 0.0572(3) 0.0737(15) Uani 1 1 d . U . . .
H22A H 0.8639 0.0138 0.0469 0.111 Uiso 1 1 calc R U . . .
H22B H 0.8029 -0.0337 0.0045 0.111 Uiso 1 1 calc R U . . .
H22C H 0.8941 -0.0391 0.0842 0.111 Uiso 1 1 calc R U . . .
B1 B 0.4536(4) 0.19179(15) 0.9932(2) 0.0416(10) Uani 1 1 d D U . . .
F1 F 0.5480(3) 0.18486(12) 0.93746(18) 0.0750(9) Uani 1 1 d D U . . .
F2 F 0.3392(3) 0.18514(14) 0.95515(18) 0.0800(10) Uani 1 1 d D U . . .
F3 F 0.4702(3) 0.16071(13) 1.05911(17) 0.0830(10) Uani 1 1 d D U . . .
F4 F 0.4578(4) 0.23943(13) 1.0213(3) 0.1072(13) Uani 1 1 d D U . . .
C23A C 0.3082(7) 0.2493(3) 0.5165(5) 0.0655(17) Uiso 0.75 1 d D . P D 1
H23A H 0.2553 0.2775 0.5019 0.098 Uiso 0.75 1 calc R U P D 1
H23B H 0.3325 0.2510 0.5753 0.098 Uiso 0.75 1 calc R U P D 1
H23C H 0.3841 0.2496 0.4829 0.098 Uiso 0.75 1 calc R U P D 1
P2A P 0.22067(13) 0.19362(5) 0.49692(8) 0.0368(3) Uani 0.75 1 d D U P D 1
H2PA H 0.151(3) 0.1923(14) 0.5588(17) 0.044 Uiso 0.75 1 d D U P E 1
C23B C 0.267(2) 0.2330(7) 0.4377(8) 0.0655(17) Uiso 0.25 1 d D . P D 2
H23D H 0.2431 0.2675 0.4370 0.098 Uiso 0.25 1 calc R U P D 2
H23E H 0.3447 0.2286 0.4064 0.098 Uiso 0.25 1 calc R U P D 2
H23F H 0.1994 0.2134 0.4122 0.098 Uiso 0.25 1 calc R U P D 2
P2B P 0.2936(6) 0.21342(16) 0.5425(3) 0.0582(13) Uani 0.25 1 d D U P D 2
H2PB H 0.402(2) 0.2296(15) 0.559(3) 0.070 Uiso 0.25 1 d D U P F 2
C24 C 0.3377(3) 0.14763(12) 0.52850(19) 0.0277(7) Uani 1 1 d D U . . .
N3 N 0.4391(2) 0.13477(10) 0.48461(16) 0.0259(6) Uani 1 1 d . U . . .
N4 N 0.3255(3) 0.11346(10) 0.58748(16) 0.0278(6) Uani 1 1 d . U . . .
C25 C 0.4899(4) 0.09289(15) 0.5162(2) 0.0418(9) Uani 1 1 d . U . . .
H25 H 0.5619 0.0762 0.4965 0.050 Uiso 1 1 calc R U . . .
C26 C 0.4195(4) 0.07956(15) 0.5804(2) 0.0415(9) Uani 1 1 d . U . . .
H26 H 0.4325 0.0517 0.6146 0.050 Uiso 1 1 calc R U . . .
C27 C 0.4857(3) 0.16243(12) 0.41556(19) 0.0264(6) Uani 1 1 d . U . . .
C28 C 0.4320(3) 0.15457(12) 0.33735(19) 0.0254(6) Uani 1 1 d . U . . .
C29 C 0.4759(3) 0.18321(12) 0.2726(2) 0.0302(7) Uani 1 1 d . U . . .
H29 H 0.4419 0.1782 0.2183 0.036 Uiso 1 1 calc R U . . .
C30 C 0.5673(4) 0.21860(13) 0.2850(2) 0.0337(8) Uani 1 1 d . U . . .
C31 C 0.6192(3) 0.22458(13) 0.3640(2) 0.0355(8) Uani 1 1 d . U . . .
H31 H 0.6824 0.2488 0.3729 0.043 Uiso 1 1 calc R U . . .
C32 C 0.5815(3) 0.19623(14) 0.4305(2) 0.0338(8) Uani 1 1 d . U . . .
C33 C 0.2329(3) 0.11424(13) 0.65218(19) 0.0292(7) Uani 1 1 d . U . . .
C34 C 0.2727(3) 0.13007(13) 0.7302(2) 0.0309(7) Uani 1 1 d . U . . .
C35 C 0.1821(4) 0.13127(14) 0.7920(2) 0.0366(8) Uani 1 1 d . U . . .
H35 H 0.2067 0.1409 0.8466 0.044 Uiso 1 1 calc R U . . .
C36 C 0.0583(4) 0.11878(14) 0.7756(2) 0.0400(9) Uani 1 1 d . U . . .
C37 C 0.0228(4) 0.10358(15) 0.6965(3) 0.0417(9) Uani 1 1 d . U . . .
H37 H -0.0629 0.0954 0.6851 0.050 Uiso 1 1 calc R U . . .
C38 C 0.1105(3) 0.09998(15) 0.6332(2) 0.0383(8) Uani 1 1 d . U . . .
C39 C 0.3307(3) 0.11719(13) 0.3221(2) 0.0324(7) Uani 1 1 d . U . . .
H39A H 0.3468 0.0887 0.3574 0.049 Uiso 1 1 calc R U . . .
H39B H 0.3308 0.1072 0.2638 0.049 Uiso 1 1 calc R U . . .
H39C H 0.2485 0.1313 0.3351 0.049 Uiso 1 1 calc R U . . .
C40 C 0.6106(5) 0.24962(14) 0.2139(3) 0.0464(10) Uani 1 1 d . U . . .
H40A H 0.5852 0.2342 0.1614 0.070 Uiso 1 1 calc R U . . .
H40B H 0.7027 0.2528 0.2167 0.070 Uiso 1 1 calc R U . . .
H40C H 0.5721 0.2821 0.2174 0.070 Uiso 1 1 calc R U . . .
C41 C 0.6428(4) 0.20155(19) 0.5154(2) 0.0538(12) Uani 1 1 d . U . . .
H41A H 0.5789 0.2111 0.5554 0.081 Uiso 1 1 calc R U . . .
H41B H 0.7085 0.2267 0.5137 0.081 Uiso 1 1 calc R U . . .
H41C H 0.6806 0.1703 0.5323 0.081 Uiso 1 1 calc R U . . .
C42 C 0.4046(4) 0.14744(16) 0.7472(2) 0.0427(9) Uani 1 1 d . U . . .
H42A H 0.4641 0.1211 0.7353 0.064 Uiso 1 1 calc R U . . .
H42B H 0.4136 0.1570 0.8055 0.064 Uiso 1 1 calc R U . . .
H42C H 0.4223 0.1756 0.7119 0.064 Uiso 1 1 calc R U . . .
C43 C -0.0386(5) 0.1233(2) 0.8426(3) 0.0606(13) Uani 1 1 d . U . . .
H43A H 0.0025 0.1185 0.8969 0.091 Uiso 1 1 calc R U . . .
H43B H -0.1041 0.0984 0.8340 0.091 Uiso 1 1 calc R U . . .
H43C H -0.0770 0.1558 0.8402 0.091 Uiso 1 1 calc R U . . .
C44 C 0.0719(5) 0.0813(2) 0.5485(3) 0.0649(14) Uani 1 1 d . U . . .
H44A H 0.0690 0.1086 0.5092 0.097 Uiso 1 1 calc R U . . .
H44B H -0.0117 0.0662 0.5511 0.097 Uiso 1 1 calc R U . . .
H44C H 0.1333 0.0571 0.5302 0.097 Uiso 1 1 calc R U . . .
B2 B -0.2607(4) 0.02464(15) 0.5978(3) 0.0599(15) Uani 1 1 d D . . . .
F5A F -0.3734(3) 0.00042(16) 0.5954(2) 0.0519(9) Uiso 0.75 1 d D U P G 1
F6A F -0.2383(4) 0.04452(14) 0.5163(2) 0.0649(9) Uiso 0.75 1 d D U P G 1
F7A F -0.1603(3) -0.00095(14) 0.6199(2) 0.0657(10) Uiso 0.75 1 d D U P G 1
F8A F -0.2802(4) 0.06658(16) 0.6438(3) 0.0831(12) Uiso 0.75 1 d D U P G 1
F5B F -0.2415(9) 0.0314(3) 0.6856(4) 0.0519(9) Uiso 0.25 1 d D U P G 2
F6B F -0.2340(10) 0.0655(3) 0.5599(6) 0.0649(9) Uiso 0.25 1 d D U P G 2
F7B F -0.1761(9) -0.0157(3) 0.5885(7) 0.0657(10) Uiso 0.25 1 d D U P G 2
F8B F -0.3744(9) 0.0027(6) 0.5793(10) 0.0831(12) Uiso 0.25 1 d D U P G 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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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
P1 C1A H1A1 109.5 . . ?
P1 C1A H1A2 109.5 . . ?
H1A1 C1A H1A2 109.5 . . ?
P1 C1A H1A3 109.5 . . ?
H1A1 C1A H1A3 109.5 . . ?
H1A2 C1A H1A3 109.5 . . ?
P1 C1B H1B1 109.5 . . ?
P1 C1B H1B2 109.5 . . ?
H1B1 C1B H1B2 109.5 . . ?
P1 C1B H1B3 109.5 . . ?
H1B1 C1B H1B3 109.5 . . ?
H1B2 C1B H1B3 109.5 . . ?
C1B P1 C2 100.2(6) . . ?
C2 P1 C1A 98.8(2) . . ?
C2 P1 H1PA 100.1(19) . . ?
C1A P1 H1PA 100.0(18) . . ?
C1B P1 H1PB 102(2) . . ?
C2 P1 H1PB 100(2) . . ?
N1 C2 N2 106.5(3) . . ?
N1 C2 P1 125.4(3) . . ?
N2 C2 P1 127.8(3) . . ?
C2 N1 C3 109.3(3) . . ?
C2 N1 C5 125.8(3) . . ?
C3 N1 C5 124.9(3) . . ?
C2 N2 C4 109.4(3) . . ?
C2 N2 C11 125.0(3) . . ?
C4 N2 C11 125.4(3) . . ?
C4 C3 N1 107.6(3) . . ?
C4 C3 H3 126.2 . . ?
N1 C3 H3 126.2 . . ?
C3 C4 N2 107.2(3) . . ?
C3 C4 H4 126.4 . . ?
N2 C4 H4 126.4 . . ?
C10 C5 C6 123.2(3) . . ?
C10 C5 N1 118.1(3) . . ?
C6 C5 N1 118.5(3) . . ?
C7 C6 C5 116.9(3) . . ?
C7 C6 C17 121.0(3) . . ?
C5 C6 C17 122.0(3) . . ?
C6 C7 C8 122.0(4) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C9 C8 C7 119.1(4) . . ?
C9 C8 C18 120.1(4) . . ?
C7 C8 C18 120.8(4) . . ?
C8 C9 C10 121.6(4) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C9 C10 C5 117.2(4) . . ?
C9 C10 C19 121.5(4) . . ?
C5 C10 C19 121.2(4) . . ?
C12 C11 C16 123.7(4) . . ?
C12 C11 N2 117.7(3) . . ?
C16 C11 N2 118.6(4) . . ?
C11 C12 C13 117.1(4) . . ?
C11 C12 C20 121.8(3) . . ?
C13 C12 C20 121.1(4) . . ?
C14 C13 C12 121.2(5) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C15 C14 C13 119.4(5) . . ?
C15 C14 C21 121.3(6) . . ?
C13 C14 C21 119.3(7) . . ?
C14 C15 C16 122.5(5) . . ?
C14 C15 H15 118.7 . . ?
C16 C15 H15 118.7 . . ?
C15 C16 C11 115.9(5) . . ?
C15 C16 C22 122.1(5) . . ?
C11 C16 C22 121.9(4) . . ?
C6 C17 H17A 109.5 . . ?
C6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C8 C18 H18A 109.5 . . ?
C8 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C8 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C12 C20 H20A 109.5 . . ?
C12 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C12 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C14 C21 H21A 109.5 . . ?
C14 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C14 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 C22 H22A 109.5 . . ?
C16 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C16 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
F2 B1 F3 111.5(3) . . ?
F2 B1 F1 109.9(3) . . ?
F3 B1 F1 109.9(3) . . ?
F2 B1 F4 107.3(3) . . ?
F3 B1 F4 109.2(3) . . ?
F1 B1 F4 109.1(4) . . ?
P2A C23A H23A 109.5 . . ?
P2A C23A H23B 109.5 . . ?
H23A C23A H23B 109.5 . . ?
P2A C23A H23C 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
C23A P2A C24 100.9(3) . . ?
C23A P2A H2PA 101.1(18) . . ?
C24 P2A H2PA 99.4(18) . . ?
P2B C23B H23D 109.5 . . ?
P2B C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
P2B C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
C23B P2B C24 101.9(6) . . ?
C23B P2B H2PB 102(2) . . ?
C24 P2B H2PB 98(2) . . ?
N4 C24 N3 106.3(3) . . ?
N4 C24 P2A 127.0(2) . . ?
N3 C24 P2A 125.2(2) . . ?
N4 C24 P2B 123.7(3) . . ?
N3 C24 P2B 121.2(3) . . ?
C24 N3 C25 109.7(3) . . ?
C24 N3 C27 124.0(3) . . ?
C25 N3 C27 126.3(3) . . ?
C24 N4 C26 109.4(3) . . ?
C24 N4 C33 125.3(3) . . ?
C26 N4 C33 125.2(3) . . ?
C26 C25 N3 107.3(3) . . ?
C26 C25 H25 126.4 . . ?
N3 C25 H25 126.4 . . ?
C25 C26 N4 107.4(3) . . ?
C25 C26 H26 126.3 . . ?
N4 C26 H26 126.3 . . ?
C32 C27 C28 122.9(3) . . ?
C32 C27 N3 118.4(3) . . ?
C28 C27 N3 118.6(3) . . ?
C27 C28 C29 117.2(3) . . ?
C27 C28 C39 122.2(3) . . ?
C29 C28 C39 120.6(3) . . ?
C30 C29 C28 121.9(3) . . ?
C30 C29 H29 119.0 . . ?
C28 C29 H29 119.0 . . ?
C29 C30 C31 118.7(3) . . ?
C29 C30 C40 120.5(3) . . ?
C31 C30 C40 120.8(3) . . ?
C30 C31 C32 121.9(3) . . ?
C30 C31 H31 119.1 . . ?
C32 C31 H31 119.1 . . ?
C31 C32 C27 117.3(3) . . ?
C31 C32 C41 121.4(3) . . ?
C27 C32 C41 121.3(3) . . ?
C38 C33 C34 123.7(3) . . ?
C38 C33 N4 118.9(3) . . ?
C34 C33 N4 117.4(3) . . ?
C33 C34 C35 117.0(3) . . ?
C33 C34 C42 122.0(3) . . ?
C35 C34 C42 120.9(3) . . ?
C36 C35 C34 121.4(3) . . ?
C36 C35 H35 119.3 . . ?
C34 C35 H35 119.3 . . ?
C35 C36 C37 119.4(3) . . ?
C35 C36 C43 120.1(4) . . ?
C37 C36 C43 120.5(4) . . ?
C36 C37 C38 121.4(4) . . ?
C36 C37 H37 119.3 . . ?
C38 C37 H37 119.3 . . ?
C33 C38 C37 116.9(3) . . ?
C33 C38 C44 122.1(4) . . ?
C37 C38 C44 120.9(4) . . ?
C28 C39 H39A 109.5 . . ?
C28 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C28 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C30 C40 H40A 109.5 . . ?
C30 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C30 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C32 C41 H41A 109.5 . . ?
C32 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C32 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C34 C42 H42A 109.5 . . ?
C34 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C34 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C36 C43 H43A 109.5 . . ?
C36 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C36 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C38 C44 H44A 109.5 . . ?
C38 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C38 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
F7A B2 F5A 116.8(4) . . ?
F6B B2 F8B 117.9(8) . . ?
F7A B2 F8A 115.2(4) . . ?
F5A B2 F8A 106.1(4) . . ?
F6B B2 F7B 117.9(7) . . ?
F8B B2 F7B 100.8(7) . . ?
F6B B2 F5B 108.8(6) . . ?
F8B B2 F5B 112.2(7) . . ?
F7B B2 F5B 97.3(6) . . ?
F7A B2 F6A 107.4(4) . . ?
F5A B2 F6A 108.4(4) . . ?
F8A B2 F6A 101.8(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
C1A P1 1.840(6) . ?
C1A H1A1 0.9800 . ?
C1A H1A2 0.9800 . ?
C1A H1A3 0.9800 . ?
C1B P1 1.807(10) . ?
C1B H1B1 0.9800 . ?
C1B H1B2 0.9800 . ?
C1B H1B3 0.9800 . ?
P1 C2 1.828(3) . ?
P1 H1PA 1.251(11) . ?
P1 H1PB 1.251(12) . ?
C2 N1 1.344(4) . ?
C2 N2 1.345(4) . ?
N1 C3 1.379(5) . ?
N1 C5 1.439(5) . ?
N2 C4 1.380(5) . ?
N2 C11 1.446(5) . ?
C3 C4 1.331(6) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C5 C10 1.392(5) . ?
C5 C6 1.398(5) . ?
C6 C7 1.385(5) . ?
C6 C17 1.503(5) . ?
C7 C8 1.387(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(6) . ?
C8 C18 1.515(6) . ?
C9 C10 1.389(6) . ?
C9 H9 0.9500 . ?
C10 C19 1.508(6) . ?
C11 C12 1.382(6) . ?
C11 C16 1.399(6) . ?
C12 C13 1.394(6) . ?
C12 C20 1.502(6) . ?
C13 C14 1.380(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.370(9) . ?
C14 C21 1.515(7) . ?
C15 C16 1.389(7) . ?
C15 H15 0.9500 . ?
C16 C22 1.489(7) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
B1 F2 1.361(4) . ?
B1 F3 1.371(4) . ?
B1 F1 1.373(4) . ?
B1 F4 1.381(4) . ?
C23A P2A 1.809(7) . ?
C23A H23A 0.9800 . ?
C23A H23B 0.9800 . ?
C23A H23C 0.9800 . ?
P2A C24 1.833(3) . ?
P2A H2PA 1.253(11) . ?
C23B P2B 1.792(10) . ?
C23B H23D 0.9800 . ?
C23B H23E 0.9800 . ?
C23B H23F 0.9800 . ?
P2B C24 1.876(5) . ?
P2B H2PB 1.251(12) . ?
C24 N4 1.343(4) . ?
C24 N3 1.346(4) . ?
N3 C25 1.362(5) . ?
N3 C27 1.444(4) . ?
N4 C26 1.368(5) . ?
N4 C33 1.449(4) . ?
C25 C26 1.340(5) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C32 1.391(5) . ?
C27 C28 1.392(4) . ?
C28 C29 1.395(5) . ?
C28 C39 1.500(5) . ?
C29 C30 1.382(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.388(5) . ?
C30 C40 1.507(5) . ?
C31 C32 1.390(5) . ?
C31 H31 0.9500 . ?
C32 C41 1.513(5) . ?
C33 C38 1.383(5) . ?
C33 C34 1.389(5) . ?
C34 C35 1.400(5) . ?
C34 C42 1.497(5) . ?
C35 C36 1.378(6) . ?
C35 H35 0.9500 . ?
C36 C37 1.387(6) . ?
C36 C43 1.512(5) . ?
C37 C38 1.399(5) . ?
C37 H37 0.9500 . ?
C38 C44 1.508(6) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
B2 F6B 1.310(6) . ?
B2 F7A 1.317(5) . ?
B2 F5A 1.367(5) . ?
B2 F8B 1.375(6) . ?
B2 F8A 1.385(5) . ?
B2 F7B 1.432(6) . ?
B2 F5B 1.439(6) . ?
B2 F6A 1.449(5) . ?
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
C1B P1 C2 N1 117.4(8) . . . . ?
C1A P1 C2 N1 87.8(4) . . . . ?
C1B P1 C2 N2 -68.5(8) . . . . ?
C1A P1 C2 N2 -98.1(4) . . . . ?
N2 C2 N1 C3 0.0(4) . . . . ?
P1 C2 N1 C3 175.1(3) . . . . ?
N2 C2 N1 C5 -177.3(3) . . . . ?
P1 C2 N1 C5 -2.1(5) . . . . ?
N1 C2 N2 C4 0.3(4) . . . . ?
P1 C2 N2 C4 -174.7(3) . . . . ?
N1 C2 N2 C11 176.7(3) . . . . ?
P1 C2 N2 C11 1.7(5) . . . . ?
C2 N1 C3 C4 -0.3(4) . . . . ?
C5 N1 C3 C4 177.0(3) . . . . ?
N1 C3 C4 N2 0.5(5) . . . . ?
C2 N2 C4 C3 -0.5(4) . . . . ?
C11 N2 C4 C3 -176.8(4) . . . . ?
C2 N1 C5 C10 86.1(4) . . . . ?
C3 N1 C5 C10 -90.8(4) . . . . ?
C2 N1 C5 C6 -98.3(4) . . . . ?
C3 N1 C5 C6 84.8(4) . . . . ?
C10 C5 C6 C7 -0.8(5) . . . . ?
N1 C5 C6 C7 -176.1(3) . . . . ?
C10 C5 C6 C17 177.0(3) . . . . ?
N1 C5 C6 C17 1.6(5) . . . . ?
C5 C6 C7 C8 0.8(5) . . . . ?
C17 C6 C7 C8 -177.0(4) . . . . ?
C6 C7 C8 C9 -1.1(5) . . . . ?
C6 C7 C8 C18 176.3(4) . . . . ?
C7 C8 C9 C10 1.4(6) . . . . ?
C18 C8 C9 C10 -176.0(4) . . . . ?
C8 C9 C10 C5 -1.4(5) . . . . ?
C8 C9 C10 C19 177.4(4) . . . . ?
C6 C5 C10 C9 1.1(5) . . . . ?
N1 C5 C10 C9 176.4(3) . . . . ?
C6 C5 C10 C19 -177.7(3) . . . . ?
N1 C5 C10 C19 -2.3(5) . . . . ?
C2 N2 C11 C12 -81.9(5) . . . . ?
C4 N2 C11 C12 93.8(4) . . . . ?
C2 N2 C11 C16 97.9(4) . . . . ?
C4 N2 C11 C16 -86.4(5) . . . . ?
C16 C11 C12 C13 -1.5(6) . . . . ?
N2 C11 C12 C13 178.3(3) . . . . ?
C16 C11 C12 C20 179.1(4) . . . . ?
N2 C11 C12 C20 -1.1(5) . . . . ?
C11 C12 C13 C14 1.0(6) . . . . ?
C20 C12 C13 C14 -179.6(4) . . . . ?
C12 C13 C14 C15 0.1(7) . . . . ?
C12 C13 C14 C21 -180.0(5) . . . . ?
C13 C14 C15 C16 -0.7(8) . . . . ?
C21 C14 C15 C16 179.3(5) . . . . ?
C14 C15 C16 C11 0.3(7) . . . . ?
C14 C15 C16 C22 179.1(5) . . . . ?
C12 C11 C16 C15 0.9(6) . . . . ?
N2 C11 C16 C15 -178.9(4) . . . . ?
C12 C11 C16 C22 -178.0(4) . . . . ?
N2 C11 C16 C22 2.3(6) . . . . ?
C23A P2A C24 N4 121.2(4) . . . . ?
C23A P2A C24 N3 -74.9(4) . . . . ?
C23B P2B C24 N4 -156.7(8) . . . . ?
C23B P2B C24 N3 60.2(8) . . . . ?
N4 C24 N3 C25 -0.2(4) . . . . ?
P2A C24 N3 C25 -166.8(3) . . . . ?
P2B C24 N3 C25 148.5(4) . . . . ?
N4 C24 N3 C27 -179.2(3) . . . . ?
P2A C24 N3 C27 14.1(5) . . . . ?
P2B C24 N3 C27 -30.6(5) . . . . ?
N3 C24 N4 C26 0.3(4) . . . . ?
P2A C24 N4 C26 166.6(3) . . . . ?
P2B C24 N4 C26 -147.4(4) . . . . ?
N3 C24 N4 C33 176.2(3) . . . . ?
P2A C24 N4 C33 -17.5(5) . . . . ?
P2B C24 N4 C33 28.6(5) . . . . ?
C24 N3 C25 C26 0.0(5) . . . . ?
C27 N3 C25 C26 179.0(3) . . . . ?
N3 C25 C26 N4 0.2(5) . . . . ?
C24 N4 C26 C25 -0.3(4) . . . . ?
C33 N4 C26 C25 -176.2(3) . . . . ?
C24 N3 C27 C32 94.5(4) . . . . ?
C25 N3 C27 C32 -84.5(4) . . . . ?
C24 N3 C27 C28 -84.8(4) . . . . ?
C25 N3 C27 C28 96.3(4) . . . . ?
C32 C27 C28 C29 -1.6(5) . . . . ?
N3 C27 C28 C29 177.6(3) . . . . ?
C32 C27 C28 C39 178.6(3) . . . . ?
N3 C27 C28 C39 -2.2(5) . . . . ?
C27 C28 C29 C30 -1.1(5) . . . . ?
C39 C28 C29 C30 178.7(3) . . . . ?
C28 C29 C30 C31 2.0(5) . . . . ?
C28 C29 C30 C40 -178.7(3) . . . . ?
C29 C30 C31 C32 -0.3(5) . . . . ?
C40 C30 C31 C32 -179.6(4) . . . . ?
C30 C31 C32 C27 -2.2(5) . . . . ?
C30 C31 C32 C41 177.3(4) . . . . ?
C28 C27 C32 C31 3.2(5) . . . . ?
N3 C27 C32 C31 -176.0(3) . . . . ?
C28 C27 C32 C41 -176.3(4) . . . . ?
N3 C27 C32 C41 4.5(5) . . . . ?
C24 N4 C33 C38 79.0(4) . . . . ?
C26 N4 C33 C38 -105.7(4) . . . . ?
C24 N4 C33 C34 -100.2(4) . . . . ?
C26 N4 C33 C34 75.1(5) . . . . ?
C38 C33 C34 C35 0.1(5) . . . . ?
N4 C33 C34 C35 179.3(3) . . . . ?
C38 C33 C34 C42 -177.1(4) . . . . ?
N4 C33 C34 C42 2.1(5) . . . . ?
C33 C34 C35 C36 -2.0(5) . . . . ?
C42 C34 C35 C36 175.2(4) . . . . ?
C34 C35 C36 C37 1.5(6) . . . . ?
C34 C35 C36 C43 -176.5(4) . . . . ?
C35 C36 C37 C38 0.9(6) . . . . ?
C43 C36 C37 C38 178.9(4) . . . . ?
C34 C33 C38 C37 2.2(6) . . . . ?
N4 C33 C38 C37 -177.0(3) . . . . ?
C34 C33 C38 C44 -177.8(4) . . . . ?
N4 C33 C38 C44 3.0(6) . . . . ?
C36 C37 C38 C33 -2.7(6) . . . . ?
C36 C37 C38 C44 177.3(4) . . . . ?
