#------------------------------------------------------------------------------
#$Date: 2020-02-28 02:23:35 +0200 (Fri, 28 Feb 2020) $
#$Revision: 248502 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/79/4037968.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_4037968
loop_
_publ_author_name
'Tendyck, Jonas C.'
'Klöcker, Hans'
'Schürmann, Lina'
'Würthwein, Ernst-Ulrich'
'Hepp, Alexander'
'Layh, Marcus'
'Uhl, Werner'
_publ_section_title
;
 Aspects of phosphaallene chemistry - heat induced formation of
 1,2-dihydrophosphetes by intramolecular nucleophilic aromatic
 substitution and photochemical generation of tricyclic phosphiranes.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03056
_journal_year                    2020
_chemical_formula_sum            'C29 H39 P'
_chemical_formula_weight         418.57
_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-2014/7
_cell_angle_alpha                85.785(2)
_cell_angle_beta                 66.306(2)
_cell_angle_gamma                69.680(3)
_cell_formula_units_Z            2
_cell_length_a                   11.0637(8)
_cell_length_b                   11.4975(8)
_cell_length_c                   12.0726(9)
_cell_measurement_reflns_used    8210
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.910
_cell_measurement_theta_min      2.196
_cell_volume                     1314.82(17)
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17144
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.963
_diffrn_reflns_theta_min         2.196
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6300
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.057
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         6217
_refine_ls_number_restraints     114
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0560
_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)+(0.0904P)²+0.1814P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1567
_refine_ls_wR_factor_ref         0.1701
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4443
_reflns_number_total             6217
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b03056_si_001.cif
_cod_data_source_block           sad_a_compound_5a
_cod_database_code               4037968
_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   0.968
_shelx_estimated_absorpt_t_max   0.991
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
P1 P 0.28932(5) 0.23911(4) 0.55585(4) 0.04417(16) Uani 1 1 d . . . . .
C1 C 0.09594(18) 0.27177(16) 0.60792(15) 0.0417(4) Uani 1 1 d . . . . .
C2 C -0.02216(19) 0.31776(17) 0.70614(15) 0.0448(4) Uani 1 1 d . . . . .
H2 H -0.1046 0.3173 0.6993 0.054 Uiso 1 1 calc R U . . .
C3 C -0.0462(2) 0.3707(2) 0.82693(17) 0.0550(5) Uani 1 1 d . . . . .
C31 C 0.0877(3) 0.3527(4) 0.8414(2) 0.1004(10) Uani 1 1 d . . . . .
H31A H 0.1460 0.2643 0.8261 0.120 Uiso 1 1 calc R U . . .
H31B H 0.0651 0.3814 0.9241 0.120 Uiso 1 1 calc R U . . .
H31C H 0.1391 0.4006 0.7833 0.120 Uiso 1 1 calc R U . . .
C32 C -0.1309(5) 0.5089(3) 0.8392(3) 0.1220(13) Uani 1 1 d . . . . .
H32A H -0.0761 0.5505 0.7754 0.146 Uiso 1 1 calc R U . . .
H32B H -0.1522 0.5449 0.9189 0.146 Uiso 1 1 calc R U . . .
H32C H -0.2190 0.5204 0.8313 0.146 Uiso 1 1 calc R U . . .
C33 C -0.1348(4) 0.3105(3) 0.9270(2) 0.1041(11) Uani 1 1 d . . . . .
H33A H -0.2220 0.3221 0.9174 0.125 Uiso 1 1 calc R U . . .
H33B H -0.1576 0.3491 1.0060 0.125 Uiso 1 1 calc R U . . .
H33C H -0.0820 0.2214 0.9224 0.125 Uiso 1 1 calc R U . . .
C4 C 0.26329(18) 0.20095(16) 0.42299(16) 0.0428(4) Uani 1 1 d . . . . .
C5 C 0.33020(18) 0.15660(17) 0.30145(16) 0.0455(4) Uani 1 1 d D . . . .
C51 C 0.4866(7) 0.1277(6) 0.2228(5) 0.0544(17) Uani 0.658(3) 1 d D U P A 1
C511 C 0.5656(4) 0.1436(7) 0.2942(4) 0.102(2) Uani 0.658(3) 1 d D U P A 1
H51A H 0.5292 0.2308 0.3252 0.123 Uiso 0.658(3) 1 calc R U P A 1
H51B H 0.6660 0.1197 0.2414 0.123 Uiso 0.658(3) 1 calc R U P A 1
H51C H 0.5528 0.0907 0.3624 0.123 Uiso 0.658(3) 1 calc R U P A 1
C512 C 0.5038(4) 0.2091(5) 0.1168(5) 0.108(2) Uani 0.658(3) 1 d D U P A 1
H51D H 0.4482 0.2004 0.0740 0.129 Uiso 0.658(3) 1 calc R U P A 1
H51E H 0.6033 0.1832 0.0610 0.129 Uiso 0.658(3) 1 calc R U P A 1
H51F H 0.4711 0.2961 0.1469 0.129 Uiso 0.658(3) 1 calc R U P A 1
C513 C 0.5614(4) -0.0076(4) 0.1679(4) 0.0887(11) Uani 0.658(3) 1 d D U P A 1
H51G H 0.5507 -0.0641 0.2333 0.106 Uiso 0.658(3) 1 calc R U P A 1
H51H H 0.6617 -0.0224 0.1204 0.106 Uiso 0.658(3) 1 calc R U P A 1
H51I H 0.5196 -0.0227 0.1151 0.106 Uiso 0.658(3) 1 calc R U P A 1
C5A C 0.4888(10) 0.1427(11) 0.2279(11) 0.062(4) Uani 0.342(3) 1 d D U P A 2
C51A C 0.5672(8) 0.0488(8) 0.2915(10) 0.092(3) Uani 0.342(3) 1 d D U P A 2
H51J H 0.6687 0.0265 0.2441 0.110 Uiso 0.342(3) 1 calc R U P A 2
H51K H 0.5415 -0.0258 0.2996 0.110 Uiso 0.342(3) 1 calc R U P A 2
H51L H 0.5422 0.0847 0.3722 0.110 Uiso 0.342(3) 1 calc R U P A 2
C51B C 0.5082(7) 0.2656(7) 0.2292(8) 0.079(2) Uani 0.342(3) 1 d D U P A 2
H51M H 0.6061 0.2567 0.1778 0.094 Uiso 0.342(3) 1 calc R U P A 2
H51N H 0.4859 0.2925 0.3124 0.094 Uiso 0.342(3) 1 calc R U P A 2
H51O H 0.4454 0.3278 0.1980 0.094 Uiso 0.342(3) 1 calc R U P A 2
C51C C 0.5350(7) 0.0859(9) 0.1014(7) 0.0887(11) Uani 0.342(3) 1 d D U P A 2
H51P H 0.4883 0.1466 0.0568 0.106 Uiso 0.342(3) 1 calc R U P A 2
H51Q H 0.5092 0.0116 0.1074 0.106 Uiso 0.342(3) 1 calc R U P A 2
H51R H 0.6373 0.0629 0.0582 0.106 Uiso 0.342(3) 1 calc R U P A 2
C6 C 0.24462(18) 0.13601(17) 0.25143(16) 0.0448(4) Uani 1 1 d . . . . .
H6 H 0.2865 0.1075 0.1681 0.054 Uiso 1 1 calc R U . . .
C7 C 0.10141(18) 0.15452(16) 0.31568(15) 0.0410(4) Uani 1 1 d D . . . .
C71 C 0.01267(19) 0.12841(17) 0.25715(16) 0.0473(4) Uani 1 1 d D . . . .
C711 C -0.1122(3) 0.2470(2) 0.2695(2) 0.0732(7) Uani 1 1 d D . . . .
H71A H -0.1710 0.2296 0.2349 0.088 Uiso 1 1 calc R U . . .
H71B H -0.0772 0.3119 0.2261 0.088 Uiso 1 1 calc R U . . .
H71C H -0.1681 0.2755 0.3555 0.088 Uiso 1 1 calc R U . . .
C712 C -0.0434(3) 0.0282(2) 0.3223(2) 0.0761(7) Uani 1 1 d D . . . .
H71D H 0.0356 -0.0475 0.3171 0.091 Uiso 1 1 calc R U . . .
H71E H -0.0989 0.0101 0.2843 0.091 Uiso 1 1 calc R U . . .
H71F H -0.1030 0.0571 0.4077 0.091 Uiso 1 1 calc R U . . .
C713 C 0.0952(3) 0.0855(3) 0.1223(2) 0.0818(8) Uani 1 1 d D . . . .
H71G H 0.1761 0.0098 0.1118 0.098 Uiso 1 1 calc R U . . .
H71H H 0.1283 0.1510 0.0782 0.098 Uiso 1 1 calc R U . . .
H71I H 0.0340 0.0683 0.0904 0.098 Uiso 1 1 calc R U . . .
C8 C 0.03817(17) 0.19813(16) 0.43770(15) 0.0414(4) Uani 1 1 d . . . . .
H8 H -0.0584 0.2106 0.4847 0.050 Uiso 1 1 calc R U . . .
C9 C 0.11923(18) 0.22273(16) 0.48850(15) 0.0407(4) Uani 1 1 d . . . . .
C10 C 0.2190(2) 0.4819(2) 0.4649(2) 0.0635(6) Uani 1 1 d . . . . .
H10A H 0.2399 0.5592 0.4539 0.076 Uiso 1 1 calc R U . . .
H10B H 0.1179 0.5009 0.5126 0.076 Uiso 1 1 calc R U . . .
H10C H 0.2460 0.4420 0.3854 0.076 Uiso 1 1 calc R U . . .
C11 C 0.30057(19) 0.39559(17) 0.53057(16) 0.0460(4) Uani 1 1 d . . . . .
C12 C 0.37289(19) 0.43498(17) 0.57542(17) 0.0486(4) Uani 1 1 d . . . . .
H12 H 0.3678 0.5187 0.5625 0.058 Uiso 1 1 calc R U . . .
C13 C 0.45969(19) 0.36837(18) 0.64220(17) 0.0496(4) Uani 1 1 d . . . . .
C14 C 0.4429(3) 0.4275(3) 0.7463(2) 0.0756(7) Uani 1 1 d . . . . .
H14 H 0.3760 0.5090 0.7733 0.091 Uiso 1 1 calc R U . . .
C15 C 0.5233(3) 0.3681(4) 0.8113(3) 0.0962(9) Uani 1 1 d . . . . .
H15 H 0.5094 0.4084 0.8836 0.115 Uiso 1 1 calc R U . . .
C16 C 0.6223(3) 0.2519(3) 0.7714(3) 0.0869(8) Uani 1 1 d . . . . .
H16 H 0.6765 0.2115 0.8164 0.104 Uiso 1 1 calc R U . . .
C17 C 0.6436(3) 0.1938(2) 0.6670(2) 0.0734(7) Uani 1 1 d . . . . .
H17 H 0.7138 0.1138 0.6387 0.088 Uiso 1 1 calc R U . . .
C18 C 0.5626(2) 0.2517(2) 0.6024(2) 0.0571(5) Uani 1 1 d . . . . .
H18 H 0.5779 0.2108 0.5299 0.068 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'
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
C11 P1 C4 103.29(8) . . ?
C11 P1 C1 102.29(8) . . ?
C4 P1 C1 73.66(8) . . ?
C2 C1 C9 130.25(16) . . ?
C2 C1 P1 139.29(14) . . ?
C9 C1 P1 90.45(11) . . ?
C1 C2 C3 130.17(17) . . ?
C1 C2 H2 114.9 . . ?
C3 C2 H2 114.9 . . ?
C31 C3 C2 113.46(18) . . ?
C31 C3 C33 109.5(2) . . ?
C2 C3 C33 108.76(17) . . ?
C31 C3 C32 109.6(2) . . ?
C2 C3 C32 107.76(18) . . ?
C33 C3 C32 107.6(3) . . ?
C3 C31 H31A 109.5 . . ?
C3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C3 C32 H32A 109.5 . . ?
C3 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C3 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C3 C33 H33A 109.5 . . ?
C3 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C3 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C5 C4 C9 120.93(16) . . ?
C5 C4 P1 144.90(14) . . ?
C9 C4 P1 93.96(12) . . ?
C4 C5 C6 115.57(15) . . ?
C4 C5 C51 125.0(3) . . ?
C6 C5 C51 119.4(3) . . ?
C4 C5 C5A 119.7(5) . . ?
C6 C5 C5A 124.5(5) . . ?
C511 C51 C512 110.7(5) . . ?
C511 C51 C5 112.3(4) . . ?
C512 C51 C5 109.6(4) . . ?
C511 C51 C513 105.1(5) . . ?
C512 C51 C513 106.4(5) . . ?
C5 C51 C513 112.4(4) . . ?
C51 C511 H51A 109.5 . . ?
C51 C511 H51B 109.5 . . ?
H51A C511 H51B 109.5 . . ?
C51 C511 H51C 109.5 . . ?
H51A C511 H51C 109.5 . . ?
H51B C511 H51C 109.5 . . ?
C51 C512 H51D 109.5 . . ?
C51 C512 H51E 109.5 . . ?
H51D C512 H51E 109.5 . . ?
C51 C512 H51F 109.5 . . ?
H51D C512 H51F 109.5 . . ?
H51E C512 H51F 109.5 . . ?
C51 C513 H51G 109.5 . . ?
C51 C513 H51H 109.5 . . ?
H51G C513 H51H 109.5 . . ?
C51 C513 H51I 109.5 . . ?
H51G C513 H51I 109.5 . . ?
H51H C513 H51I 109.5 . . ?
C51B C5A C51A 111.5(9) . . ?
C51B C5A C51C 113.8(9) . . ?
C51A C5A C51C 107.9(9) . . ?
C51B C5A C5 110.5(7) . . ?
C51A C5A C5 104.7(8) . . ?
C51C C5A C5 107.9(8) . . ?
C5A C51A H51J 109.5 . . ?
C5A C51A H51K 109.5 . . ?
H51J C51A H51K 109.5 . . ?
C5A C51A H51L 109.5 . . ?
H51J C51A H51L 109.5 . . ?
H51K C51A H51L 109.5 . . ?
C5A C51B H51M 109.5 . . ?
C5A C51B H51N 109.5 . . ?
H51M C51B H51N 109.5 . . ?
C5A C51B H51O 109.5 . . ?
H51M C51B H51O 109.5 . . ?
H51N C51B H51O 109.5 . . ?
C5A C51C H51P 109.5 . . ?
C5A C51C H51Q 109.5 . . ?
H51P C51C H51Q 109.5 . . ?
C5A C51C H51R 109.5 . . ?
H51P C51C H51R 109.5 . . ?
H51Q C51C H51R 109.5 . . ?
C5 C6 C7 124.50(16) . . ?
C5 C6 H6 117.8 . . ?
C7 C6 H6 117.8 . . ?
C8 C7 C6 118.30(15) . . ?
C8 C7 C71 119.22(15) . . ?
C6 C7 C71 122.49(15) . . ?
C712 C71 C713 108.45(19) . . ?
C712 C71 C711 108.73(19) . . ?
C713 C71 C711 107.84(18) . . ?
C712 C71 C7 109.18(16) . . ?
C713 C71 C7 113.13(16) . . ?
C711 C71 C7 109.41(15) . . ?
C71 C711 H71A 109.5 . . ?
C71 C711 H71B 109.5 . . ?
H71A C711 H71B 109.5 . . ?
C71 C711 H71C 109.5 . . ?
H71A C711 H71C 109.5 . . ?
H71B C711 H71C 109.5 . . ?
C71 C712 H71D 109.5 . . ?
C71 C712 H71E 109.5 . . ?
H71D C712 H71E 109.5 . . ?
C71 C712 H71F 109.5 . . ?
H71D C712 H71F 109.5 . . ?
H71E C712 H71F 109.5 . . ?
C71 C713 H71G 109.5 . . ?
C71 C713 H71H 109.5 . . ?
H71G C713 H71H 109.5 . . ?
C71 C713 H71I 109.5 . . ?
H71G C713 H71I 109.5 . . ?
H71H C713 H71I 109.5 . . ?
C9 C8 C7 118.43(15) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C8 C9 C4 122.22(16) . . ?
C8 C9 C1 136.32(16) . . ?
C4 C9 C1 101.46(14) . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C10 120.12(17) . . ?
C12 C11 P1 120.89(14) . . ?
C10 C11 P1 118.88(14) . . ?
C11 C12 C13 129.88(17) . . ?
C11 C12 H12 115.1 . . ?
C13 C12 H12 115.1 . . ?
C18 C13 C14 118.2(2) . . ?
C18 C13 C12 123.01(18) . . ?
C14 C13 C12 118.72(19) . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 120.1(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 120.3(2) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 119.9(3) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C13 C18 C17 120.9(2) . . ?
C13 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
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
P1 C11 1.8411(19) . ?
P1 C4 1.8468(18) . ?
P1 C1 1.8733(18) . ?
C1 C2 1.327(3) . ?
C1 C9 1.477(2) . ?
C2 C3 1.508(2) . ?
C2 H2 0.9500 . ?
C3 C31 1.501(3) . ?
C3 C33 1.515(3) . ?
C3 C32 1.522(4) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C4 C5 1.391(2) . ?
C4 C9 1.403(2) . ?
C5 C6 1.398(2) . ?
C5 C51 1.527(7) . ?
C5 C5A 1.570(10) . ?
C51 C511 1.509(7) . ?
C51 C512 1.517(7) . ?
C51 C513 1.537(7) . ?
C511 H51A 0.9800 . ?
C511 H51B 0.9800 . ?
C511 H51C 0.9800 . ?
C512 H51D 0.9800 . ?
C512 H51E 0.9800 . ?
C512 H51F 0.9800 . ?
C513 H51G 0.9800 . ?
C513 H51H 0.9800 . ?
C513 H51I 0.9800 . ?
C5A C51B 1.504(12) . ?
C5A C51A 1.507(12) . ?
C5A C51C 1.519(12) . ?
C51A H51J 0.9800 . ?
C51A H51K 0.9800 . ?
C51A H51L 0.9800 . ?
C51B H51M 0.9800 . ?
C51B H51N 0.9800 . ?
C51B H51O 0.9800 . ?
C51C H51P 0.9800 . ?
C51C H51Q 0.9800 . ?
C51C H51R 0.9800 . ?
C6 C7 1.400(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.396(2) . ?
C7 C71 1.532(2) . ?
C71 C712 1.518(3) . ?
C71 C713 1.529(3) . ?
C71 C711 1.531(3) . ?
C711 H71A 0.9800 . ?
C711 H71B 0.9800 . ?
C711 H71C 0.9800 . ?
C712 H71D 0.9800 . ?
C712 H71E 0.9800 . ?
C712 H71F 0.9800 . ?
C713 H71G 0.9800 . ?
C713 H71H 0.9800 . ?
C713 H71I 0.9800 . ?
C8 C9 1.380(2) . ?
C8 H8 0.9500 . ?
C10 C11 1.505(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.332(3) . ?
C12 C13 1.476(3) . ?
C12 H12 0.9500 . ?
C13 C18 1.386(3) . ?
C13 C14 1.387(3) . ?
C14 C15 1.391(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.368(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.365(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C18 H18 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
C11 P1 C1 C2 -75.4(2) . . . . ?
C4 P1 C1 C2 -175.9(2) . . . . ?
C11 P1 C1 C9 104.89(11) . . . . ?
C4 P1 C1 C9 4.44(10) . . . . ?
C9 C1 C2 C3 -178.30(18) . . . . ?
P1 C1 C2 C3 2.1(4) . . . . ?
C1 C2 C3 C31 -8.7(3) . . . . ?
C1 C2 C3 C33 -130.8(3) . . . . ?
C1 C2 C3 C32 112.9(3) . . . . ?
C11 P1 C4 C5 82.1(3) . . . . ?
C1 P1 C4 C5 -178.8(3) . . . . ?
C11 P1 C4 C9 -103.83(12) . . . . ?
C1 P1 C4 C9 -4.69(11) . . . . ?
C9 C4 C5 C6 0.0(3) . . . . ?
P1 C4 C5 C6 173.11(18) . . . . ?
C9 C4 C5 C51 -178.8(3) . . . . ?
P1 C4 C5 C51 -5.7(5) . . . . ?
C9 C4 C5 C5A 175.4(5) . . . . ?
P1 C4 C5 C5A -11.5(6) . . . . ?
C4 C5 C51 C511 4.2(7) . . . . ?
C6 C5 C51 C511 -174.5(4) . . . . ?
C4 C5 C51 C512 -119.3(4) . . . . ?
C6 C5 C51 C512 61.9(6) . . . . ?
C4 C5 C51 C513 122.6(4) . . . . ?
C6 C5 C51 C513 -56.2(5) . . . . ?
C4 C5 C5A C51B -58.1(10) . . . . ?
C6 C5 C5A C51B 116.9(7) . . . . ?
C4 C5 C5A C51A 62.1(9) . . . . ?
C6 C5 C5A C51A -122.9(7) . . . . ?
C4 C5 C5A C51C 176.8(6) . . . . ?
C6 C5 C5A C51C -8.2(11) . . . . ?
C4 C5 C6 C7 -1.4(3) . . . . ?
C51 C5 C6 C7 177.5(3) . . . . ?
C5A C5 C6 C7 -176.6(6) . . . . ?
C5 C6 C7 C8 0.9(3) . . . . ?
C5 C6 C7 C71 -178.91(17) . . . . ?
C8 C7 C71 C712 -61.1(2) . . . . ?
C6 C7 C71 C712 118.7(2) . . . . ?
C8 C7 C71 C713 178.02(18) . . . . ?
C6 C7 C71 C713 -2.1(3) . . . . ?
C8 C7 C71 C711 57.8(2) . . . . ?
C6 C7 C71 C711 -122.4(2) . . . . ?
C6 C7 C8 C9 1.0(3) . . . . ?
C71 C7 C8 C9 -179.14(15) . . . . ?
C7 C8 C9 C4 -2.4(3) . . . . ?
C7 C8 C9 C1 177.69(18) . . . . ?
C5 C4 C9 C8 2.0(3) . . . . ?
P1 C4 C9 C8 -174.08(15) . . . . ?
C5 C4 C9 C1 -178.11(16) . . . . ?
P1 C4 C9 C1 5.83(13) . . . . ?
C2 C1 C9 C8 -5.6(3) . . . . ?
P1 C1 C9 C8 174.2(2) . . . . ?
C2 C1 C9 C4 174.53(19) . . . . ?
P1 C1 C9 C4 -5.73(13) . . . . ?
C4 P1 C11 C12 -152.58(16) . . . . ?
C1 P1 C11 C12 131.57(16) . . . . ?
C4 P1 C11 C10 31.26(17) . . . . ?
C1 P1 C11 C10 -44.60(17) . . . . ?
C10 C11 C12 C13 -179.94(19) . . . . ?
P1 C11 C12 C13 3.9(3) . . . . ?
C11 C12 C13 C18 49.6(3) . . . . ?
C11 C12 C13 C14 -133.9(2) . . . . ?
C18 C13 C14 C15 -2.9(3) . . . . ?
C12 C13 C14 C15 -179.6(2) . . . . ?
C13 C14 C15 C16 1.6(4) . . . . ?
C14 C15 C16 C17 0.5(4) . . . . ?
C15 C16 C17 C18 -1.3(4) . . . . ?
C14 C13 C18 C17 2.1(3) . . . . ?
C12 C13 C18 C17 178.65(19) . . . . ?
C16 C17 C18 C13 0.0(3) . . . . ?
