#------------------------------------------------------------------------------
#$Date: 2022-08-19 01:53:53 +0300 (Fri, 19 Aug 2022) $
#$Revision: 277312 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/10/7711012.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_7711012
loop_
_publ_author_name
'Rosenboom, Jan'
'Villinger, Alexander'
'Schulz, Axel'
'Bresien, Jonas'
_publ_section_title
;
 Concerted addition of aldehydes to the singlet biradical [P(μ-NTer)]2
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT02229J
_journal_year                    2022
_chemical_formula_moiety         'C55 H55 Cl N2 O P2'
_chemical_formula_sum            'C55 H55 Cl N2 O P2'
_chemical_formula_weight         857.40
_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-2014/7
_audit_update_record
;
2021-12-02 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.821(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.060(3)
_cell_length_b                   24.498(6)
_cell_length_c                   16.669(4)
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.93
_cell_measurement_theta_min      2.58
_cell_volume                     4603(2)
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_collection       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Apex Kappa-II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            91246
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         3.084
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_correction_T_min  0.6518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description       block
_exptl_crystal_F_000             1816
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     562
_refine_ls_number_reflns         13415
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0487
_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)+(0.0629P)²+1.1376P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1269
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9680
_reflns_number_total             13415
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt02229j2.cif
_cod_data_source_block           is_jrb23
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7711012
_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   0.957
_shelx_estimated_absorpt_t_max   0.968
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
Cl1 Cl 0.59078(4) 0.44778(2) 0.89129(3) 0.03296(11) Uani 1 1 d . . . . .
P1 P 0.38469(4) 0.75179(2) 0.72873(3) 0.01888(9) Uani 1 1 d . . . . .
P2 P 0.22501(3) 0.68138(2) 0.70459(2) 0.01724(9) Uani 1 1 d . . . . .
O1 O 0.43957(9) 0.70954(5) 0.81243(7) 0.0213(2) Uani 1 1 d . . . . .
N1 N 0.23907(11) 0.75110(5) 0.72565(8) 0.0178(3) Uani 1 1 d . . . . .
N2 N 0.32552(11) 0.70030(5) 0.65321(8) 0.0183(3) Uani 1 1 d . . . . .
C1 C 0.18321(13) 0.79017(6) 0.76137(9) 0.0172(3) Uani 1 1 d . . . . .
C2 C 0.12015(13) 0.77651(6) 0.81564(10) 0.0181(3) Uani 1 1 d . . . . .
C3 C 0.06991(14) 0.81794(7) 0.84905(10) 0.0220(3) Uani 1 1 d . . . . .
H3 H 0.0272 0.8087 0.8853 0.026 Uiso 1 1 calc R U . . .
C4 C 0.08118(15) 0.87218(7) 0.83043(11) 0.0239(3) Uani 1 1 d . . . . .
H4 H 0.0494 0.9001 0.8554 0.029 Uiso 1 1 calc R U . . .
C5 C 0.13934(14) 0.88529(7) 0.77488(10) 0.0221(3) Uani 1 1 d . . . . .
H5 H 0.1463 0.9225 0.7615 0.026 Uiso 1 1 calc R U . . .
C6 C 0.18777(13) 0.84521(6) 0.73822(10) 0.0187(3) Uani 1 1 d . . . . .
C7 C 0.10061(14) 0.71883(6) 0.83529(10) 0.0194(3) Uani 1 1 d . . . . .
C8 C 0.01767(14) 0.68660(7) 0.77267(11) 0.0230(3) Uani 1 1 d . . . . .
C9 C 0.00590(16) 0.63180(7) 0.79038(13) 0.0299(4) Uani 1 1 d . . . . .
H9 H -0.0486 0.6097 0.7475 0.036 Uiso 1 1 calc R U . . .
C10 C 0.07156(17) 0.60871(7) 0.86882(14) 0.0330(4) Uani 1 1 d . . . . .
C11 C 0.14657(17) 0.64237(7) 0.93231(12) 0.0298(4) Uani 1 1 d . . . . .
H11 H 0.1883 0.6275 0.9874 0.036 Uiso 1 1 calc R U . . .
C12 C 0.16218(15) 0.69700(7) 0.91742(10) 0.0235(3) Uani 1 1 d . . . . .
C13 C -0.05954(15) 0.71014(8) 0.68772(11) 0.0278(4) Uani 1 1 d . . . . .
H13A H -0.0174 0.7084 0.6472 0.042 Uiso 1 1 calc R U . . .
H13B H -0.0782 0.7482 0.6956 0.042 Uiso 1 1 calc R U . . .
H13C H -0.1332 0.6891 0.6651 0.042 Uiso 1 1 calc R U . . .
C14 C 0.0663(2) 0.54817(8) 0.88276(18) 0.0502(6) Uani 1 1 d . . . . .
H14A H -0.0163 0.5358 0.8586 0.075 Uiso 1 1 calc R U . . .
H14B H 0.0982 0.5403 0.9444 0.075 Uiso 1 1 calc R U . . .
H14C H 0.1134 0.5290 0.8543 0.075 Uiso 1 1 calc R U . . .
C15 C 0.24618(16) 0.73149(8) 0.98738(11) 0.0302(4) Uani 1 1 d . . . . .
H15A H 0.3055 0.7478 0.9670 0.045 Uiso 1 1 calc R U . . .
H15B H 0.2860 0.7087 1.0377 0.045 Uiso 1 1 calc R U . . .
H15C H 0.2018 0.7605 1.0031 0.045 Uiso 1 1 calc R U . . .
C16 C 0.23308(14) 0.86275(6) 0.66934(10) 0.0192(3) Uani 1 1 d . . . . .
C17 C 0.33846(14) 0.89261(6) 0.68847(10) 0.0210(3) Uani 1 1 d . . . . .
C18 C 0.36971(15) 0.91268(7) 0.62127(11) 0.0234(3) Uani 1 1 d . . . . .
H18 H 0.4416 0.9326 0.6344 0.028 Uiso 1 1 calc R U . . .
C19 C 0.29960(15) 0.90466(7) 0.53593(11) 0.0248(3) Uani 1 1 d . . . . .
C20 C 0.19578(15) 0.87464(7) 0.51805(10) 0.0252(3) Uani 1 1 d . . . . .
H20 H 0.1471 0.8684 0.4599 0.030 Uiso 1 1 calc R U . . .
C21 C 0.16120(14) 0.85350(7) 0.58295(10) 0.0214(3) Uani 1 1 d . . . . .
C22 C 0.42129(15) 0.90155(7) 0.77962(11) 0.0273(4) Uani 1 1 d . . . . .
H22A H 0.4686 0.8685 0.8007 0.041 Uiso 1 1 calc R U . . .
H22B H 0.3749 0.9097 0.8160 0.041 Uiso 1 1 calc R U . . .
H22C H 0.4742 0.9323 0.7814 0.041 Uiso 1 1 calc R U . . .
C23 C 0.33616(18) 0.92705(8) 0.46489(12) 0.0338(4) Uani 1 1 d . . . . .
H23A H 0.3154 0.9008 0.4174 0.051 Uiso 1 1 calc R U . . .
H23B H 0.4220 0.9333 0.4866 0.051 Uiso 1 1 calc R U . . .
H23C H 0.2948 0.9616 0.4444 0.051 Uiso 1 1 calc R U . . .
C24 C 0.04747(15) 0.82129(7) 0.55995(11) 0.0266(4) Uani 1 1 d . . . . .
H24A H 0.0037 0.8240 0.4981 0.040 Uiso 1 1 calc R U . . .
H24B H -0.0011 0.8360 0.5911 0.040 Uiso 1 1 calc R U . . .
H24C H 0.0660 0.7829 0.5757 0.040 Uiso 1 1 calc R U . . .
C25 C 0.38267(14) 0.66604(7) 0.61144(10) 0.0200(3) Uani 1 1 d . . . . .
C26 C 0.49847(15) 0.67788(7) 0.61252(10) 0.0231(3) Uani 1 1 d . . . . .
C27 C 0.55144(17) 0.64165(8) 0.57262(12) 0.0312(4) Uani 1 1 d . . . . .
H27 H 0.6296 0.6490 0.5744 0.037 Uiso 1 1 calc R U . . .
C28 C 0.49417(19) 0.59560(8) 0.53077(13) 0.0359(4) Uani 1 1 d . . . . .
H28 H 0.5333 0.5708 0.5059 0.043 Uiso 1 1 calc R U . . .
C29 C 0.37856(18) 0.58595(8) 0.52553(12) 0.0316(4) Uani 1 1 d . . . . .
H29 H 0.3376 0.5550 0.4947 0.038 Uiso 1 1 calc R U . . .
C30 C 0.32086(15) 0.62063(7) 0.56443(10) 0.0230(3) Uani 1 1 d . . . . .
C31 C 0.56170(14) 0.73002(7) 0.64739(11) 0.0238(3) Uani 1 1 d . . . . .
C32 C 0.52735(15) 0.77744(7) 0.59675(11) 0.0258(4) Uani 1 1 d . . . . .
C33 C 0.58500(16) 0.82614(8) 0.62673(12) 0.0305(4) Uani 1 1 d . . . . .
H33 H 0.5616 0.8578 0.5919 0.037 Uiso 1 1 calc R U . . .
C34 C 0.67587(16) 0.83035(8) 0.70586(13) 0.0339(4) Uani 1 1 d . . . . .
C35 C 0.71204(16) 0.78298(8) 0.75338(12) 0.0326(4) Uani 1 1 d . . . . .
H35 H 0.7757 0.7849 0.8070 0.039 Uiso 1 1 calc R U . . .
C36 C 0.65876(15) 0.73280(8) 0.72569(11) 0.0278(4) Uani 1 1 d . . . . .
C37 C 0.42798(17) 0.77602(8) 0.51026(11) 0.0309(4) Uani 1 1 d . . . . .
H37A H 0.4390 0.8056 0.4742 0.046 Uiso 1 1 calc R U . . .
H37B H 0.3518 0.7807 0.5181 0.046 Uiso 1 1 calc R U . . .
H37C H 0.4288 0.7409 0.4824 0.046 Uiso 1 1 calc R U . . .
C38 C 0.7344(2) 0.88436(10) 0.73891(17) 0.0499(6) Uani 1 1 d . . . . .
H38A H 0.8178 0.8830 0.7438 0.075 Uiso 1 1 calc R U . . .
H38B H 0.7298 0.8917 0.7954 0.075 Uiso 1 1 calc R U . . .
H38C H 0.6937 0.9135 0.6990 0.075 Uiso 1 1 calc R U . . .
C39 C 0.70708(16) 0.68388(9) 0.78188(12) 0.0346(4) Uani 1 1 d . . . . .
H39A H 0.6932 0.6510 0.7463 0.052 Uiso 1 1 calc R U . . .
H39B H 0.6671 0.6803 0.8235 0.052 Uiso 1 1 calc R U . . .
H39C H 0.7925 0.6886 0.8124 0.052 Uiso 1 1 calc R U . . .
C40 C 0.19427(15) 0.60959(7) 0.55358(10) 0.0231(3) Uani 1 1 d . . . . .
C41 C 0.16251(15) 0.56409(7) 0.59203(11) 0.0256(3) Uani 1 1 d . . . . .
C42 C 0.04421(16) 0.55673(8) 0.58353(12) 0.0303(4) Uani 1 1 d . . . . .
H42 H 0.0233 0.5260 0.6100 0.036 Uiso 1 1 calc R U . . .
C43 C -0.04374(16) 0.59287(8) 0.53758(11) 0.0314(4) Uani 1 1 d . . . . .
C44 C -0.01196(16) 0.63626(8) 0.49738(11) 0.0311(4) Uani 1 1 d . . . . .
H44 H -0.0719 0.6607 0.4643 0.037 Uiso 1 1 calc R U . . .
C45 C 0.10467(16) 0.64542(7) 0.50355(10) 0.0269(4) Uani 1 1 d . . . . .
C46 C 0.25191(17) 0.52300(7) 0.64496(12) 0.0306(4) Uani 1 1 d . . . . .
H46A H 0.2285 0.4863 0.6215 0.046 Uiso 1 1 calc R U . . .
H46B H 0.2550 0.5242 0.7045 0.046 Uiso 1 1 calc R U . . .
H46C H 0.3303 0.5317 0.6432 0.046 Uiso 1 1 calc R U . . .
C47 C -0.17027(17) 0.58475(10) 0.53274(14) 0.0441(5) Uani 1 1 d . . . . .
H47A H -0.2243 0.6034 0.4819 0.066 Uiso 1 1 calc R U . . .
H47B H -0.1797 0.5999 0.5844 0.066 Uiso 1 1 calc R U . . .
H47C H -0.1888 0.5457 0.5288 0.066 Uiso 1 1 calc R U . . .
C48 C 0.13312(18) 0.69267(8) 0.45666(12) 0.0343(4) Uani 1 1 d . . . . .
H48A H 0.1785 0.6796 0.4220 0.051 Uiso 1 1 calc R U . . .
H48B H 0.1802 0.7197 0.4983 0.051 Uiso 1 1 calc R U . . .
H48C H 0.0592 0.7096 0.4191 0.051 Uiso 1 1 calc R U . . .
C49 C 0.35348(14) 0.66736(6) 0.81003(10) 0.0199(3) Uani 1 1 d . . . . .
H49 H 0.3241 0.6748 0.8580 0.024 Uiso 1 1 calc R U . . .
C50 C 0.40815(14) 0.61136(7) 0.82417(10) 0.0198(3) Uani 1 1 d . . . . .
C51 C 0.49264(15) 0.59520(7) 0.78962(10) 0.0239(3) Uani 1 1 d . . . . .
H51 H 0.5133 0.6193 0.7525 0.029 Uiso 1 1 calc R U . . .
C52 C 0.54699(15) 0.54452(7) 0.80853(11) 0.0255(3) Uani 1 1 d . . . . .
H52 H 0.6055 0.5342 0.7855 0.031 Uiso 1 1 calc R U . . .
C53 C 0.51501(15) 0.50931(7) 0.86133(10) 0.0239(3) Uani 1 1 d . . . . .
C54 C 0.42691(15) 0.52288(7) 0.89278(11) 0.0264(4) Uani 1 1 d . . . . .
H54 H 0.4023 0.4975 0.9263 0.032 Uiso 1 1 calc R U . . .
C55 C 0.37489(15) 0.57421(7) 0.87459(11) 0.0246(3) Uani 1 1 d . . . . .
H55 H 0.3155 0.5841 0.8970 0.029 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'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 '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
O1 P1 N1 96.58(6) . . ?
O1 P1 N2 95.36(6) . . ?
N1 P1 N2 79.74(6) . . ?
O1 P1 P2 76.23(4) . . ?
N1 P1 P2 43.86(4) . . ?
N2 P1 P2 45.07(4) . . ?
N1 P2 N2 78.87(6) . . ?
N1 P2 C49 90.10(7) . . ?
N2 P2 C49 91.21(7) . . ?
N1 P2 P1 43.82(4) . . ?
N2 P2 P1 44.08(4) . . ?
C49 P2 P1 69.63(5) . . ?
C49 O1 P1 110.45(9) . . ?
C1 N1 P1 127.36(11) . . ?
C1 N1 P2 136.12(11) . . ?
P1 N1 P2 92.33(6) . . ?
C25 N2 P1 129.59(11) . . ?
C25 N2 P2 128.11(11) . . ?
P1 N2 P2 90.85(6) . . ?
C6 C1 C2 118.95(14) . . ?
C6 C1 N1 117.42(13) . . ?
C2 C1 N1 123.58(14) . . ?
C3 C2 C1 119.47(15) . . ?
C3 C2 C7 118.53(14) . . ?
C1 C2 C7 121.93(13) . . ?
C4 C3 C2 121.22(15) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 119.16(15) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 121.49(15) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 119.48(14) . . ?
C5 C6 C16 117.31(14) . . ?
C1 C6 C16 122.98(14) . . ?
C8 C7 C12 119.90(15) . . ?
C8 C7 C2 119.81(14) . . ?
C12 C7 C2 120.25(14) . . ?
C9 C8 C7 118.94(16) . . ?
C9 C8 C13 119.54(16) . . ?
C7 C8 C13 121.51(15) . . ?
C10 C9 C8 121.76(17) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C9 C10 C11 118.33(17) . . ?
C9 C10 C14 120.4(2) . . ?
C11 C10 C14 121.2(2) . . ?
C12 C11 C10 121.91(17) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C7 118.80(16) . . ?
C11 C12 C15 120.05(16) . . ?
C7 C12 C15 121.13(15) . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 119.66(15) . . ?
C17 C16 C6 121.55(14) . . ?
C21 C16 C6 118.48(14) . . ?
C18 C17 C16 118.96(15) . . ?
C18 C17 C22 119.16(15) . . ?
C16 C17 C22 121.82(15) . . ?
C19 C18 C17 122.31(15) . . ?
C19 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
C18 C19 C20 118.00(15) . . ?
C18 C19 C23 120.85(16) . . ?
C20 C19 C23 121.15(16) . . ?
C19 C20 C21 121.78(15) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C20 C21 C16 119.28(15) . . ?
C20 C21 C24 119.61(14) . . ?
C16 C21 C24 121.12(15) . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C23 H23A 109.5 . . ?
C19 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C19 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C30 C25 N2 119.13(14) . . ?
C30 C25 C26 119.40(14) . . ?
N2 C25 C26 121.40(15) . . ?
C27 C26 C25 118.66(16) . . ?
C27 C26 C31 118.23(15) . . ?
C25 C26 C31 122.87(14) . . ?
C28 C27 C26 122.13(18) . . ?
C28 C27 H27 118.9 . . ?
C26 C27 H27 118.9 . . ?
C27 C28 C29 118.95(17) . . ?
C27 C28 H28 120.5 . . ?
C29 C28 H28 120.5 . . ?
C28 C29 C30 121.57(18) . . ?
C28 C29 H29 119.2 . . ?
C30 C29 H29 119.2 . . ?
C29 C30 C25 119.06(16) . . ?
C29 C30 C40 119.31(16) . . ?
C25 C30 C40 121.62(14) . . ?
C32 C31 C36 119.00(17) . . ?
C32 C31 C26 118.08(15) . . ?
C36 C31 C26 122.78(15) . . ?
C33 C32 C31 119.49(17) . . ?
C33 C32 C37 119.40(16) . . ?
C31 C32 C37 121.12(16) . . ?
C32 C33 C34 122.28(18) . . ?
C32 C33 H33 118.9 . . ?
C34 C33 H33 118.9 . . ?
C35 C34 C33 117.60(18) . . ?
C35 C34 C38 120.97(19) . . ?
C33 C34 C38 121.44(19) . . ?
C34 C35 C36 122.51(18) . . ?
C34 C35 H35 118.7 . . ?
C36 C35 H35 118.7 . . ?
C35 C36 C31 118.95(17) . . ?
C35 C36 C39 117.85(17) . . ?
C31 C36 C39 123.19(17) . . ?
C32 C37 H37A 109.5 . . ?
C32 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C32 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C34 C38 H38A 109.5 . . ?
C34 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C34 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C41 C40 C45 119.16(16) . . ?
C41 C40 C30 121.33(15) . . ?
C45 C40 C30 119.51(16) . . ?
C42 C41 C40 119.41(16) . . ?
C42 C41 C46 117.75(17) . . ?
C40 C41 C46 122.81(16) . . ?
C43 C42 C41 121.90(18) . . ?
C43 C42 H42 119.0 . . ?
C41 C42 H42 119.0 . . ?
C44 C43 C42 118.04(17) . . ?
C44 C43 C47 121.60(18) . . ?
C42 C43 C47 120.36(19) . . ?
C43 C44 C45 122.39(17) . . ?
C43 C44 H44 118.8 . . ?
C45 C44 H44 118.8 . . ?
C44 C45 C40 118.99(17) . . ?
C44 C45 C48 119.82(16) . . ?
C40 C45 C48 121.18(17) . . ?
C41 C46 H46A 109.5 . . ?
C41 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C41 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C43 C47 H47A 109.5 . . ?
C43 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C43 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C45 C48 H48A 109.5 . . ?
C45 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C45 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
O1 C49 C50 112.00(13) . . ?
O1 C49 P2 103.55(10) . . ?
C50 C49 P2 118.27(11) . . ?
O1 C49 H49 107.5 . . ?
C50 C49 H49 107.5 . . ?
P2 C49 H49 107.5 . . ?
C55 C50 C51 118.29(15) . . ?
C55 C50 C49 119.14(14) . . ?
C51 C50 C49 122.57(14) . . ?
C52 C51 C50 121.07(16) . . ?
C52 C51 H51 119.5 . . ?
C50 C51 H51 119.5 . . ?
C53 C52 C51 119.16(16) . . ?
C53 C52 H52 120.4 . . ?
C51 C52 H52 120.4 . . ?
C52 C53 C54 121.18(15) . . ?
C52 C53 Cl1 119.10(13) . . ?
C54 C53 Cl1 119.69(13) . . ?
C53 C54 C55 118.89(16) . . ?
C53 C54 H54 120.6 . . ?
C55 C54 H54 120.6 . . ?
C54 C55 C50 121.27(16) . . ?
C54 C55 H55 119.4 . . ?
C50 C55 H55 119.4 . . ?
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
Cl1 C53 1.7412(17) . ?
P1 O1 1.6732(12) . ?
P1 N1 1.7387(14) . ?
P1 N2 1.7456(14) . ?
P1 P2 2.5091(7) . ?
P2 N1 1.7398(14) . ?
P2 N2 1.7765(14) . ?
P2 C49 1.9162(16) . ?
O1 C49 1.4553(19) . ?
N1 C1 1.4176(19) . ?
N2 C25 1.416(2) . ?
C1 C6 1.409(2) . ?
C1 C2 1.414(2) . ?
C2 C3 1.395(2) . ?
C2 C7 1.488(2) . ?
C3 C4 1.382(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(2) . ?
C5 H5 0.9500 . ?
C6 C16 1.499(2) . ?
C7 C8 1.404(2) . ?
C7 C12 1.410(2) . ?
C8 C9 1.392(2) . ?
C8 C13 1.506(2) . ?
C9 C10 1.386(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(3) . ?
C10 C14 1.506(3) . ?
C11 C12 1.386(2) . ?
C11 H11 0.9500 . ?
C12 C15 1.504(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.401(2) . ?
C16 C21 1.410(2) . ?
C17 C18 1.392(2) . ?
C17 C22 1.508(2) . ?
C18 C19 1.386(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.390(2) . ?
C19 C23 1.506(2) . ?
C20 C21 1.390(2) . ?
C20 H20 0.9500 . ?
C21 C24 1.509(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C30 1.411(2) . ?
C25 C26 1.420(2) . ?
C26 C27 1.393(2) . ?
C26 C31 1.495(2) . ?
C27 C28 1.376(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.386(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.395(2) . ?
C29 H29 0.9500 . ?
C30 C40 1.497(2) . ?
C31 C32 1.409(2) . ?
C31 C36 1.411(2) . ?
C32 C33 1.382(3) . ?
C32 C37 1.513(2) . ?
C33 C34 1.387(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.385(3) . ?
C34 C38 1.509(3) . ?
C35 C36 1.388(3) . ?
C35 H35 0.9500 . ?
C36 C39 1.505(3) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 C41 1.405(2) . ?
C40 C45 1.412(2) . ?
C41 C42 1.394(3) . ?
C41 C46 1.509(2) . ?
C42 C43 1.385(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.382(3) . ?
C43 C47 1.512(3) . ?
C44 C45 1.392(3) . ?
C44 H44 0.9500 . ?
C45 C48 1.503(3) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 C50 1.504(2) . ?
C49 H49 1.0000 . ?
C50 C55 1.391(2) . ?
C50 C51 1.394(2) . ?
C51 C52 1.387(2) . ?
C51 H51 0.9500 . ?
C52 C53 1.382(2) . ?
C52 H52 0.9500 . ?
C53 C54 1.382(2) . ?
C54 C55 1.390(2) . ?
C54 H54 0.9500 . ?
C55 H55 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
N1 P1 O1 C49 36.20(11) . . . . ?
N2 P1 O1 C49 -44.06(10) . . . . ?
P2 P1 O1 C49 -2.94(9) . . . . ?
O1 P1 N1 C1 97.58(13) . . . . ?
N2 P1 N1 C1 -168.14(14) . . . . ?
P2 P1 N1 C1 159.81(16) . . . . ?
O1 P1 N1 P2 -62.23(6) . . . . ?
N2 P1 N1 P2 32.05(6) . . . . ?
N2 P2 N1 C1 171.79(16) . . . . ?
C49 P2 N1 C1 -97.00(15) . . . . ?
P1 P2 N1 C1 -156.68(18) . . . . ?
N2 P2 N1 P1 -31.53(6) . . . . ?
C49 P2 N1 P1 59.69(7) . . . . ?
O1 P1 N2 C25 -79.97(14) . . . . ?
N1 P1 N2 C25 -175.71(14) . . . . ?
P2 P1 N2 C25 -144.42(16) . . . . ?
O1 P1 N2 P2 64.45(6) . . . . ?
N1 P1 N2 P2 -31.29(6) . . . . ?
N1 P2 N2 C25 176.63(14) . . . . ?
C49 P2 N2 C25 86.76(13) . . . . ?
P1 P2 N2 C25 145.26(16) . . . . ?
N1 P2 N2 P1 31.37(6) . . . . ?
C49 P2 N2 P1 -58.50(7) . . . . ?
P1 N1 C1 C6 53.67(18) . . . . ?
P2 N1 C1 C6 -156.17(13) . . . . ?
P1 N1 C1 C2 -128.85(14) . . . . ?
P2 N1 C1 C2 21.3(2) . . . . ?
C6 C1 C2 C3 -3.7(2) . . . . ?
N1 C1 C2 C3 178.82(14) . . . . ?
C6 C1 C2 C7 173.38(14) . . . . ?
N1 C1 C2 C7 -4.1(2) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C7 C2 C3 C4 -177.55(15) . . . . ?
C2 C3 C4 C5 2.6(2) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C4 C5 C6 C1 -3.4(2) . . . . ?
C4 C5 C6 C16 171.29(15) . . . . ?
C2 C1 C6 C5 5.5(2) . . . . ?
N1 C1 C6 C5 -176.86(14) . . . . ?
C2 C1 C6 C16 -168.79(14) . . . . ?
N1 C1 C6 C16 8.8(2) . . . . ?
C3 C2 C7 C8 103.09(18) . . . . ?
C1 C2 C7 C8 -74.05(19) . . . . ?
C3 C2 C7 C12 -74.81(19) . . . . ?
C1 C2 C7 C12 108.05(17) . . . . ?
C12 C7 C8 C9 -6.0(2) . . . . ?
C2 C7 C8 C9 176.08(14) . . . . ?
C12 C7 C8 C13 173.14(15) . . . . ?
C2 C7 C8 C13 -4.8(2) . . . . ?
C7 C8 C9 C10 1.7(2) . . . . ?
C13 C8 C9 C10 -177.46(16) . . . . ?
C8 C9 C10 C11 3.2(3) . . . . ?
C8 C9 C10 C14 -173.59(17) . . . . ?
C9 C10 C11 C12 -3.8(3) . . . . ?
C14 C10 C11 C12 172.89(17) . . . . ?
C10 C11 C12 C7 -0.4(2) . . . . ?
C10 C11 C12 C15 -178.67(16) . . . . ?
C8 C7 C12 C11 5.4(2) . . . . ?
C2 C7 C12 C11 -176.73(14) . . . . ?
C8 C7 C12 C15 -176.38(15) . . . . ?
C2 C7 C12 C15 1.5(2) . . . . ?
C5 C6 C16 C17 73.1(2) . . . . ?
C1 C6 C16 C17 -112.45(18) . . . . ?
C5 C6 C16 C21 -100.46(18) . . . . ?
C1 C6 C16 C21 74.0(2) . . . . ?
C21 C16 C17 C18 0.2(2) . . . . ?
C6 C16 C17 C18 -173.33(14) . . . . ?
C21 C16 C17 C22 -177.23(15) . . . . ?
C6 C16 C17 C22 9.3(2) . . . . ?
C16 C17 C18 C19 0.7(2) . . . . ?
C22 C17 C18 C19 178.14(16) . . . . ?
C17 C18 C19 C20 -1.1(3) . . . . ?
C17 C18 C19 C23 179.90(16) . . . . ?
C18 C19 C20 C21 0.7(3) . . . . ?
C23 C19 C20 C21 179.70(16) . . . . ?
C19 C20 C21 C16 0.1(3) . . . . ?
C19 C20 C21 C24 179.88(16) . . . . ?
C17 C16 C21 C20 -0.5(2) . . . . ?
C6 C16 C21 C20 173.15(15) . . . . ?
C17 C16 C21 C24 179.69(15) . . . . ?
C6 C16 C21 C24 -6.6(2) . . . . ?
P1 N2 C25 C30 168.52(12) . . . . ?
P2 N2 C25 C30 36.2(2) . . . . ?
P1 N2 C25 C26 -14.5(2) . . . . ?
P2 N2 C25 C26 -146.81(13) . . . . ?
C30 C25 C26 C27 -5.1(2) . . . . ?
N2 C25 C26 C27 177.93(15) . . . . ?
C30 C25 C26 C31 169.06(15) . . . . ?
N2 C25 C26 C31 -7.9(2) . . . . ?
C25 C26 C27 C28 1.5(3) . . . . ?
C31 C26 C27 C28 -172.95(17) . . . . ?
C26 C27 C28 C29 2.3(3) . . . . ?
C27 C28 C29 C30 -2.5(3) . . . . ?
C28 C29 C30 C25 -1.1(3) . . . . ?
C28 C29 C30 C40 177.42(17) . . . . ?
N2 C25 C30 C29 -178.03(14) . . . . ?
C26 C25 C30 C29 4.9(2) . . . . ?
N2 C25 C30 C40 3.5(2) . . . . ?
C26 C25 C30 C40 -173.59(14) . . . . ?
C27 C26 C31 C32 97.67(19) . . . . ?
C25 C26 C31 C32 -76.5(2) . . . . ?
C27 C26 C31 C36 -78.0(2) . . . . ?
C25 C26 C31 C36 107.85(19) . . . . ?
C36 C31 C32 C33 -3.4(2) . . . . ?
C26 C31 C32 C33 -179.25(15) . . . . ?
C36 C31 C32 C37 176.88(15) . . . . ?
C26 C31 C32 C37 1.1(2) . . . . ?
C31 C32 C33 C34 -0.4(3) . . . . ?
C37 C32 C33 C34 179.26(16) . . . . ?
C32 C33 C34 C35 3.1(3) . . . . ?
C32 C33 C34 C38 -177.58(18) . . . . ?
C33 C34 C35 C36 -1.8(3) . . . . ?
C38 C34 C35 C36 178.80(18) . . . . ?
C34 C35 C36 C31 -2.0(3) . . . . ?
C34 C35 C36 C39 178.82(17) . . . . ?
C32 C31 C36 C35 4.6(2) . . . . ?
C26 C31 C36 C35 -179.81(15) . . . . ?
C32 C31 C36 C39 -176.25(16) . . . . ?
C26 C31 C36 C39 -0.6(2) . . . . ?
C29 C30 C40 C41 69.3(2) . . . . ?
C25 C30 C40 C41 -112.24(18) . . . . ?
C29 C30 C40 C45 -110.54(19) . . . . ?
C25 C30 C40 C45 68.0(2) . . . . ?
C45 C40 C41 C42 -3.1(2) . . . . ?
C30 C40 C41 C42 177.06(15) . . . . ?
C45 C40 C41 C46 178.65(15) . . . . ?
C30 C40 C41 C46 -1.1(2) . . . . ?
C40 C41 C42 C43 0.5(3) . . . . ?
C46 C41 C42 C43 178.77(16) . . . . ?
C41 C42 C43 C44 2.0(3) . . . . ?
C41 C42 C43 C47 -177.57(17) . . . . ?
C42 C43 C44 C45 -1.8(3) . . . . ?
C47 C43 C44 C45 177.77(17) . . . . ?
C43 C44 C45 C40 -0.9(3) . . . . ?
C43 C44 C45 C48 178.65(16) . . . . ?
C41 C40 C45 C44 3.3(2) . . . . ?
C30 C40 C45 C44 -176.87(15) . . . . ?
C41 C40 C45 C48 -176.19(15) . . . . ?
C30 C40 C45 C48 3.6(2) . . . . ?
P1 O1 C49 C50 132.37(11) . . . . ?
P1 O1 C49 P2 3.85(11) . . . . ?
O1 C49 C50 C55 140.14(15) . . . . ?
P2 C49 C50 C55 -99.58(16) . . . . ?
O1 C49 C50 C51 -38.9(2) . . . . ?
P2 C49 C50 C51 81.35(18) . . . . ?
C55 C50 C51 C52 -3.4(2) . . . . ?
C49 C50 C51 C52 175.71(15) . . . . ?
C50 C51 C52 C53 1.1(3) . . . . ?
C51 C52 C53 C54 2.5(3) . . . . ?
C51 C52 C53 Cl1 -175.39(13) . . . . ?
C52 C53 C54 C55 -3.7(3) . . . . ?
Cl1 C53 C54 C55 174.17(13) . . . . ?
C53 C54 C55 C50 1.3(3) . . . . ?
C51 C50 C55 C54 2.1(2) . . . . ?
C49 C50 C55 C54 -176.99(15) . . . . ?
