#------------------------------------------------------------------------------
#$Date: 2022-08-19 01:53:53 +0300 (Fri, 19 Aug 2022) $
#$Revision: 277312 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/10/7711011.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_7711011
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 H56 N2 O P2, 0.5(C6 H6)'
_chemical_formula_sum            'C58 H59 N2 O P2'
_chemical_formula_weight         862.01
_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   mixed
_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                 108.606(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8530(5)
_cell_length_b                   24.4713(9)
_cell_length_c                   16.8584(6)
_cell_measurement_reflns_used    9998
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.84
_cell_measurement_theta_min      2.68
_cell_volume                     4634.3(3)
_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 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 QUEST diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0895
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            106140
_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         30.999
_diffrn_reflns_theta_min         3.539
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.6753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       block
_exptl_crystal_F_000             1836
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     599
_refine_ls_number_reflns         14743
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0489
_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)+(0.0466P)²+2.6669P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1299
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10397
_reflns_number_total             14743
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt02229j2.cif
_cod_data_source_block           av_jrb18
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7711011
_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   0.985
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
N1 N 0.16644(11) 0.70912(5) 0.52562(8) 0.0167(2) Uani 1 1 d . . . . .
N2 N 0.32904(11) 0.75721(5) 0.59241(8) 0.0166(2) Uani 1 1 d . . . . .
O1 O 0.21411(10) 0.71596(4) 0.68194(7) 0.0210(2) Uani 1 1 d . . . . .
P1 P 0.31684(3) 0.68777(2) 0.56894(2) 0.01603(8) Uani 1 1 d . . . . .
P2 P 0.18770(3) 0.75964(2) 0.60185(2) 0.01730(8) Uani 1 1 d . . . . .
C1 C 0.06560(13) 0.67584(6) 0.48941(9) 0.0170(3) Uani 1 1 d . . . . .
C2 C 0.07629(13) 0.62983(6) 0.44154(9) 0.0184(3) Uani 1 1 d . . . . .
C3 C -0.02192(14) 0.59617(7) 0.40794(10) 0.0240(3) Uani 1 1 d . . . . .
H3 H -0.0139 0.5647 0.3772 0.029 Uiso 1 1 calc R U . . .
C4 C -0.13121(15) 0.60724(7) 0.41803(11) 0.0268(3) Uani 1 1 d . . . . .
H4 H -0.1966 0.5831 0.3963 0.032 Uiso 1 1 calc R U . . .
C5 C -0.14296(14) 0.65416(7) 0.46048(10) 0.0239(3) Uani 1 1 d . . . . .
H5 H -0.2184 0.6627 0.4658 0.029 Uiso 1 1 calc R U . . .
C6 C -0.04739(13) 0.68922(6) 0.49569(9) 0.0187(3) Uani 1 1 d . . . . .
C7 C 0.18930(13) 0.61727(6) 0.42387(9) 0.0184(3) Uani 1 1 d . . . . .
C8 C 0.22973(14) 0.65324(6) 0.37341(9) 0.0212(3) Uani 1 1 d . . . . .
C9 C 0.33824(15) 0.64299(7) 0.36070(10) 0.0255(3) Uani 1 1 d . . . . .
H9 H 0.3659 0.6677 0.3276 0.031 Uiso 1 1 calc R U . . .
C10 C 0.40717(15) 0.59772(7) 0.39495(11) 0.0278(4) Uani 1 1 d . . . . .
C11 C 0.36304(15) 0.56146(7) 0.44059(11) 0.0270(3) Uani 1 1 d . . . . .
H11 H 0.4080 0.5296 0.4627 0.032 Uiso 1 1 calc R U . . .
C12 C 0.25510(14) 0.56973(6) 0.45549(10) 0.0213(3) Uani 1 1 d . . . . .
C13 C 0.15730(16) 0.70187(7) 0.33194(11) 0.0283(4) Uani 1 1 d . . . . .
H13A H 0.1606 0.7300 0.3741 0.043 Uiso 1 1 calc R U . . .
H13B H 0.0745 0.6907 0.3051 0.043 Uiso 1 1 calc R U . . .
H13C H 0.1896 0.7167 0.2897 0.043 Uiso 1 1 calc R U . . .
C14 C 0.52485(18) 0.58764(9) 0.38086(14) 0.0405(5) Uani 1 1 d . . . . .
H14A H 0.5880 0.5852 0.4350 0.061 Uiso 1 1 calc R U . . .
H14B H 0.5421 0.6178 0.3483 0.061 Uiso 1 1 calc R U . . .
H14C H 0.5209 0.5533 0.3501 0.061 Uiso 1 1 calc R U . . .
C15 C 0.21284(16) 0.52736(7) 0.50430(11) 0.0280(4) Uani 1 1 d . . . . .
H15A H 0.1622 0.5007 0.4656 0.042 Uiso 1 1 calc R U . . .
H15B H 0.1671 0.5452 0.5363 0.042 Uiso 1 1 calc R U . . .
H15C H 0.2817 0.5086 0.5428 0.042 Uiso 1 1 calc R U . . .
C16 C -0.07196(13) 0.74253(6) 0.53060(10) 0.0207(3) Uani 1 1 d . . . . .
C17 C -0.08796(14) 0.74724(7) 0.60936(10) 0.0249(3) Uani 1 1 d . . . . .
C18 C -0.10724(15) 0.79908(8) 0.63713(12) 0.0308(4) Uani 1 1 d . . . . .
H18 H -0.1157 0.8026 0.6911 0.037 Uiso 1 1 calc R U . . .
C19 C -0.11452(16) 0.84556(8) 0.58909(13) 0.0329(4) Uani 1 1 d . . . . .
C20 C -0.10722(15) 0.83953(7) 0.50923(12) 0.0298(4) Uani 1 1 d . . . . .
H20 H -0.1169 0.8707 0.4742 0.036 Uiso 1 1 calc R U . . .
C21 C -0.08608(14) 0.78908(7) 0.47899(10) 0.0236(3) Uani 1 1 d . . . . .
C22 C -0.08457(16) 0.69951(8) 0.66583(11) 0.0311(4) Uani 1 1 d . . . . .
H22A H -0.0039 0.6954 0.7053 0.047 Uiso 1 1 calc R U . . .
H22B H -0.1069 0.6662 0.6322 0.047 Uiso 1 1 calc R U . . .
H22C H -0.1406 0.7057 0.6969 0.047 Uiso 1 1 calc R U . . .
C23 C -0.1308(2) 0.90120(9) 0.62297(16) 0.0482(6) Uani 1 1 d . . . . .
H23A H -0.2141 0.9058 0.6202 0.072 Uiso 1 1 calc R U . . .
H23B H -0.1094 0.9296 0.5894 0.072 Uiso 1 1 calc R U . . .
H23C H -0.0794 0.9042 0.6813 0.072 Uiso 1 1 calc R U . . .
C24 C -0.07659(16) 0.78545(7) 0.39236(11) 0.0283(4) Uani 1 1 d . . . . .
H24A H -0.1139 0.8176 0.3600 0.042 Uiso 1 1 calc R U . . .
H24B H -0.1172 0.7524 0.3647 0.042 Uiso 1 1 calc R U . . .
H24C H 0.0075 0.7840 0.3959 0.042 Uiso 1 1 calc R U . . .
C25 C 0.42423(13) 0.79401(6) 0.62600(9) 0.0162(3) Uani 1 1 d . . . . .
C26 C 0.40171(13) 0.84981(6) 0.60525(9) 0.0177(3) Uani 1 1 d . . . . .
C27 C 0.49096(14) 0.88812(6) 0.63940(10) 0.0223(3) Uani 1 1 d . . . . .
H27 H 0.4754 0.9257 0.6265 0.027 Uiso 1 1 calc R U . . .
C28 C 0.60208(14) 0.87236(6) 0.69189(10) 0.0236(3) Uani 1 1 d . . . . .
H28 H 0.6613 0.8990 0.7163 0.028 Uiso 1 1 calc R U . . .
C29 C 0.62570(14) 0.81753(6) 0.70833(10) 0.0212(3) Uani 1 1 d . . . . .
H29 H 0.7029 0.8067 0.7425 0.025 Uiso 1 1 calc R U . . .
C30 C 0.53929(13) 0.77764(6) 0.67603(9) 0.0172(3) Uani 1 1 d . . . . .
C31 C 0.28886(13) 0.86957(6) 0.54279(9) 0.0191(3) Uani 1 1 d . . . . .
C32 C 0.26684(14) 0.85830(6) 0.45729(10) 0.0214(3) Uani 1 1 d . . . . .
C33 C 0.16688(15) 0.88089(7) 0.39854(10) 0.0254(3) Uani 1 1 d . . . . .
H33 H 0.1510 0.8725 0.3410 0.031 Uiso 1 1 calc R U . . .
C34 C 0.09002(15) 0.91531(7) 0.42176(11) 0.0266(3) Uani 1 1 d . . . . .
C35 C 0.11299(15) 0.92603(7) 0.50630(11) 0.0257(3) Uani 1 1 d . . . . .
H35 H 0.0608 0.9495 0.5230 0.031 Uiso 1 1 calc R U . . .
C36 C 0.21052(14) 0.90333(6) 0.56753(10) 0.0218(3) Uani 1 1 d . . . . .
C37 C 0.35099(16) 0.82341(7) 0.42822(11) 0.0271(3) Uani 1 1 d . . . . .
H37A H 0.3440 0.7852 0.4435 0.041 Uiso 1 1 calc R U . . .
H37B H 0.4329 0.8360 0.4549 0.041 Uiso 1 1 calc R U . . .
H37C H 0.3308 0.8263 0.3673 0.041 Uiso 1 1 calc R U . . .
C38 C -0.01659(17) 0.94019(8) 0.35711(12) 0.0359(4) Uani 1 1 d . . . . .
H38A H 0.0088 0.9719 0.3316 0.054 Uiso 1 1 calc R U . . .
H38B H -0.0747 0.9518 0.3840 0.054 Uiso 1 1 calc R U . . .
H38C H -0.0530 0.9130 0.3138 0.054 Uiso 1 1 calc R U . . .
C39 C 0.22590(17) 0.91369(7) 0.65835(11) 0.0288(4) Uani 1 1 d . . . . .
H39A H 0.1673 0.9407 0.6628 0.043 Uiso 1 1 calc R U . . .
H39B H 0.3063 0.9276 0.6864 0.043 Uiso 1 1 calc R U . . .
H39C H 0.2141 0.8795 0.6850 0.043 Uiso 1 1 calc R U . . .
C40 C 0.57505(13) 0.71923(6) 0.69298(10) 0.0191(3) Uani 1 1 d . . . . .
C41 C 0.59704(14) 0.69728(6) 0.77364(10) 0.0230(3) Uani 1 1 d . . . . .
C42 C 0.63117(15) 0.64265(7) 0.78742(12) 0.0298(4) Uani 1 1 d . . . . .
H42 H 0.6470 0.6278 0.8420 0.036 Uiso 1 1 calc R U . . .
C43 C 0.64266(15) 0.60928(7) 0.72406(13) 0.0330(4) Uani 1 1 d . . . . .
C44 C 0.62558(15) 0.63229(7) 0.64586(12) 0.0305(4) Uani 1 1 d . . . . .
H44 H 0.6357 0.6102 0.6023 0.037 Uiso 1 1 calc R U . . .
C45 C 0.59390(13) 0.68704(6) 0.62948(10) 0.0228(3) Uani 1 1 d . . . . .
C46 C 0.58331(17) 0.73100(7) 0.84463(10) 0.0290(4) Uani 1 1 d . . . . .
H46A H 0.5963 0.7078 0.8942 0.043 Uiso 1 1 calc R U . . .
H46B H 0.5029 0.7464 0.8285 0.043 Uiso 1 1 calc R U . . .
H46C H 0.6419 0.7607 0.8575 0.043 Uiso 1 1 calc R U . . .
C47 C 0.67008(19) 0.54901(8) 0.73876(17) 0.0491(6) Uani 1 1 d . . . . .
H47A H 0.5981 0.5277 0.7116 0.074 Uiso 1 1 calc R U . . .
H47B H 0.6972 0.5416 0.7990 0.074 Uiso 1 1 calc R U . . .
H47C H 0.7327 0.5388 0.7152 0.074 Uiso 1 1 calc R U . . .
C48 C 0.58625(15) 0.71108(7) 0.54566(11) 0.0276(3) Uani 1 1 d . . . . .
H48A H 0.6571 0.7334 0.5513 0.041 Uiso 1 1 calc R U . . .
H48B H 0.5149 0.7340 0.5256 0.041 Uiso 1 1 calc R U . . .
H48C H 0.5818 0.6815 0.5055 0.041 Uiso 1 1 calc R U . . .
C49 C 0.29427(14) 0.67307(6) 0.67416(10) 0.0192(3) Uani 1 1 d . . . . .
C50 C 0.25289(14) 0.61674(6) 0.68648(9) 0.0204(3) Uani 1 1 d . . . . .
C51 C 0.33808(16) 0.57698(7) 0.72002(11) 0.0278(4) Uani 1 1 d . . . . .
H51 H 0.4200 0.5858 0.7328 0.033 Uiso 1 1 calc R U . . .
C52 C 0.30551(17) 0.52460(7) 0.73515(12) 0.0322(4) Uani 1 1 d . . . . .
H52 H 0.3649 0.4977 0.7579 0.039 Uiso 1 1 calc R U . . .
C53 C 0.18672(17) 0.51148(7) 0.71720(10) 0.0294(4) Uani 1 1 d . . . . .
H53 H 0.1642 0.4760 0.7293 0.035 Uiso 1 1 calc R U . . .
C54 C 0.10039(16) 0.55034(7) 0.68145(10) 0.0278(3) Uani 1 1 d . . . . .
H54 H 0.0185 0.5412 0.6678 0.033 Uiso 1 1 calc R U . . .
C55 C 0.13342(15) 0.60267(7) 0.66551(10) 0.0237(3) Uani 1 1 d . . . . .
H55 H 0.0739 0.6290 0.6401 0.028 Uiso 1 1 calc R U . . .
H49 H 0.3700(18) 0.6799(8) 0.7142(12) 0.026(5) Uiso 1 1 d . . . . .
C56 C 0.4623(14) 0.5392(8) 0.9434(10) 0.0331(14) Uani 0.5 1 d G U P A -1
H56 H 0.4421 0.5669 0.9017 0.040 Uiso 0.5 1 calc R U P A -1
C57 C 0.3731(14) 0.5099(8) 0.9614(10) 0.0369(16) Uani 0.5 1 d G U P A -1
H57 H 0.2918 0.5174 0.9319 0.044 Uiso 0.5 1 calc R U P A -1
C58 C 0.4026(14) 0.4695(8) 1.0225(10) 0.0388(18) Uani 0.5 1 d G U P A -1
H58 H 0.3416 0.4494 1.0348 0.047 Uiso 0.5 1 calc R U P A -1
C59 C 0.5214(14) 0.4584(8) 1.0656(10) 0.041(2) Uani 0.5 1 d G U P A -1
H59 H 0.5416 0.4308 1.1074 0.049 Uiso 0.5 1 calc R U P A -1
C60 C 0.6107(14) 0.4878(8) 1.0477(10) 0.0383(18) Uani 0.5 1 d G U P A -1
H60 H 0.6919 0.4802 1.0771 0.046 Uiso 0.5 1 calc R U P A -1
C61 C 0.5811(14) 0.5282(8) 0.9866(10) 0.0362(16) Uani 0.5 1 d G U P A -1
H61 H 0.6421 0.5483 0.9743 0.043 Uiso 0.5 1 calc R U P A -1
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'
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
C1 N1 P2 129.09(10) . . ?
C1 N1 P1 127.41(10) . . ?
P2 N1 P1 90.88(6) . . ?
C25 N2 P2 127.78(10) . . ?
C25 N2 P1 135.33(10) . . ?
P2 N2 P1 92.40(6) . . ?
C49 O1 P2 110.44(9) . . ?
N2 P1 N1 78.81(6) . . ?
N2 P1 C49 89.93(6) . . ?
N1 P1 C49 91.01(6) . . ?
N2 P1 P2 43.70(4) . . ?
N1 P1 P2 44.02(4) . . ?
C49 P1 P2 69.53(5) . . ?
O1 P2 N2 96.59(6) . . ?
O1 P2 N1 95.04(6) . . ?
N2 P2 N1 79.90(6) . . ?
O1 P2 P1 76.11(4) . . ?
N2 P2 P1 43.90(4) . . ?
N1 P2 P1 45.09(4) . . ?
N1 C1 C2 119.19(13) . . ?
N1 C1 C6 121.62(13) . . ?
C2 C1 C6 119.08(13) . . ?
C3 C2 C1 119.23(14) . . ?
C3 C2 C7 118.96(13) . . ?
C1 C2 C7 121.79(13) . . ?
C4 C3 C2 121.86(15) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C5 C4 C3 118.56(15) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 121.93(15) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C1 119.06(14) . . ?
C5 C6 C16 118.04(14) . . ?
C1 C6 C16 122.57(13) . . ?
C12 C7 C8 119.38(14) . . ?
C12 C7 C2 121.22(14) . . ?
C8 C7 C2 119.39(13) . . ?
C9 C8 C7 119.27(15) . . ?
C9 C8 C13 119.31(15) . . ?
C7 C8 C13 121.42(15) . . ?
C10 C9 C8 121.98(16) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C11 C10 C9 117.83(16) . . ?
C11 C10 C14 121.08(17) . . ?
C9 C10 C14 121.07(17) . . ?
C10 C11 C12 122.62(16) . . ?
C10 C11 H11 118.7 . . ?
C12 C11 H11 118.7 . . ?
C11 C12 C7 118.74(15) . . ?
C11 C12 C15 118.87(15) . . ?
C7 C12 C15 122.39(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 119.45(15) . . ?
C17 C16 C6 123.02(15) . . ?
C21 C16 C6 117.43(14) . . ?
C18 C17 C16 118.52(17) . . ?
C18 C17 C22 117.98(16) . . ?
C16 C17 C22 123.50(15) . . ?
C19 C18 C17 122.50(17) . . ?
C19 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
C18 C19 C20 118.07(16) . . ?
C18 C19 C23 120.72(19) . . ?
C20 C19 C23 121.21(19) . . ?
C19 C20 C21 121.75(18) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C20 C21 C16 119.43(16) . . ?
C20 C21 C24 119.18(16) . . ?
C16 C21 C24 121.39(14) . . ?
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 . . ?
N2 C25 C30 123.60(13) . . ?
N2 C25 C26 116.93(13) . . ?
C30 C25 C26 119.44(13) . . ?
C27 C26 C25 119.28(14) . . ?
C27 C26 C31 117.68(13) . . ?
C25 C26 C31 122.87(13) . . ?
C28 C27 C26 121.20(14) . . ?
C28 C27 H27 119.4 . . ?
C26 C27 H27 119.4 . . ?
C29 C28 C27 119.27(14) . . ?
C29 C28 H28 120.4 . . ?
C27 C28 H28 120.4 . . ?
C28 C29 C30 121.71(14) . . ?
C28 C29 H29 119.1 . . ?
C30 C29 H29 119.1 . . ?
C29 C30 C25 118.91(13) . . ?
C29 C30 C40 117.88(13) . . ?
C25 C30 C40 123.15(13) . . ?
C36 C31 C32 119.73(14) . . ?
C36 C31 C26 120.66(14) . . ?
C32 C31 C26 119.34(14) . . ?
C33 C32 C31 119.21(15) . . ?
C33 C32 C37 119.60(15) . . ?
C31 C32 C37 121.18(14) . . ?
C34 C33 C32 121.79(15) . . ?
C34 C33 H33 119.1 . . ?
C32 C33 H33 119.1 . . ?
C33 C34 C35 118.27(15) . . ?
C33 C34 C38 121.05(16) . . ?
C35 C34 C38 120.68(16) . . ?
C34 C35 C36 121.93(16) . . ?
C34 C35 H35 119.0 . . ?
C36 C35 H35 119.0 . . ?
C35 C36 C31 119.04(15) . . ?
C35 C36 C39 119.22(15) . . ?
C31 C36 C39 121.69(14) . . ?
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 . . ?
C45 C40 C41 119.84(14) . . ?
C45 C40 C30 119.75(14) . . ?
C41 C40 C30 120.30(14) . . ?
C42 C41 C40 118.78(16) . . ?
C42 C41 C46 119.50(15) . . ?
C40 C41 C46 121.71(14) . . ?
C43 C42 C41 122.09(17) . . ?
C43 C42 H42 119.0 . . ?
C41 C42 H42 119.0 . . ?
C42 C43 C44 118.22(15) . . ?
C42 C43 C47 121.13(19) . . ?
C44 C43 C47 120.64(19) . . ?
C43 C44 C45 121.75(17) . . ?
C43 C44 H44 119.1 . . ?
C45 C44 H44 119.1 . . ?
C44 C45 C40 119.11(16) . . ?
C44 C45 C48 119.51(15) . . ?
C40 C45 C48 121.32(14) . . ?
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 113.59(13) . . ?
O1 C49 P1 103.76(9) . . ?
C50 C49 P1 116.77(11) . . ?
O1 C49 H49 107.9(12) . . ?
C50 C49 H49 109.8(12) . . ?
P1 C49 H49 104.3(12) . . ?
C51 C50 C55 118.73(15) . . ?
C51 C50 C49 118.28(14) . . ?
C55 C50 C49 122.99(14) . . ?
C52 C51 C50 120.99(16) . . ?
C52 C51 H51 119.5 . . ?
C50 C51 H51 119.5 . . ?
C53 C52 C51 119.96(17) . . ?
C53 C52 H52 120.0 . . ?
C51 C52 H52 120.0 . . ?
C52 C53 C54 119.71(15) . . ?
C52 C53 H53 120.1 . . ?
C54 C53 H53 120.1 . . ?
C53 C54 C55 120.12(16) . . ?
C53 C54 H54 119.9 . . ?
C55 C54 H54 119.9 . . ?
C50 C55 C54 120.42(16) . . ?
C50 C55 H55 119.8 . . ?
C54 C55 H55 119.8 . . ?
C57 C56 C61 120.0 . . ?
C57 C56 H56 120.0 . . ?
C61 C56 H56 120.0 . . ?
C58 C57 C56 120.0 . . ?
C58 C57 H57 120.0 . . ?
C56 C57 H57 120.0 . . ?
C57 C58 C59 120.0 . . ?
C57 C58 H58 120.0 . . ?
C59 C58 H58 120.0 . . ?
C58 C59 C60 120.0 . . ?
C58 C59 H59 120.0 . . ?
C60 C59 H59 120.0 . . ?
C61 C60 C59 120.0 . . ?
C61 C60 H60 120.0 . . ?
C59 C60 H60 120.0 . . ?
C60 C61 C56 120.0 . . ?
C60 C61 H61 120.0 . . ?
C56 C61 H61 120.0 . . ?
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
N1 C1 1.4138(18) . ?
N1 P2 1.7426(13) . ?
N1 P1 1.7759(13) . ?
N2 C25 1.4133(18) . ?
N2 P2 1.7337(13) . ?
N2 P1 1.7401(12) . ?
O1 C49 1.4493(19) . ?
O1 P2 1.6715(11) . ?
P1 C49 1.9105(16) . ?
P1 P2 2.5071(5) . ?
C1 C2 1.414(2) . ?
C1 C6 1.415(2) . ?
C2 C3 1.391(2) . ?
C2 C7 1.494(2) . ?
C3 C4 1.386(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(2) . ?
C5 H5 0.9500 . ?
C6 C16 1.497(2) . ?
C7 C12 1.407(2) . ?
C7 C8 1.410(2) . ?
C8 C9 1.393(2) . ?
C8 C13 1.503(2) . ?
C9 C10 1.388(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(3) . ?
C10 C14 1.508(3) . ?
C11 C12 1.395(2) . ?
C11 H11 0.9500 . ?
C12 C15 1.505(2) . ?
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 1.405(2) . ?
C16 C21 1.411(2) . ?
C17 C18 1.396(2) . ?
C17 C22 1.499(3) . ?
C18 C19 1.383(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.384(3) . ?
C19 C23 1.513(3) . ?
C20 C21 1.389(2) . ?
C20 H20 0.9500 . ?
C21 C24 1.503(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 1.413(2) . ?
C25 C26 1.414(2) . ?
C26 C27 1.393(2) . ?
C26 C31 1.494(2) . ?
C27 C28 1.387(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.381(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.394(2) . ?
C29 H29 0.9500 . ?
C30 C40 1.492(2) . ?
C31 C36 1.402(2) . ?
C31 C32 1.408(2) . ?
C32 C33 1.393(2) . ?
C32 C37 1.509(2) . ?
C33 C34 1.386(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.388(2) . ?
C34 C38 1.509(2) . ?
C35 C36 1.396(2) . ?
C35 H35 0.9500 . ?
C36 C39 1.505(2) . ?
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 C45 1.403(2) . ?
C40 C41 1.407(2) . ?
C41 C42 1.395(2) . ?
C41 C46 1.505(2) . ?
C42 C43 1.385(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.388(3) . ?
C43 C47 1.514(2) . ?
C44 C45 1.395(2) . ?
C44 H44 0.9500 . ?
C45 C48 1.506(2) . ?
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 1.500(2) . ?
C49 H49 0.95(2) . ?
C50 C51 1.386(2) . ?
C50 C55 1.389(2) . ?
C51 C52 1.386(2) . ?
C51 H51 0.9500 . ?
C52 C53 1.380(3) . ?
C52 H52 0.9500 . ?
C53 C54 1.386(3) . ?
C53 H53 0.9500 . ?
C54 C55 1.390(2) . ?
C54 H54 0.9500 . ?
C55 H55 0.9500 . ?
C56 C57 1.3900 . ?
C56 C61 1.3900 . ?
C56 H56 0.9500 . ?
C57 C58 1.3900 . ?
C57 H57 0.9500 . ?
C58 C59 1.3900 . ?
C58 H58 0.9500 . ?
C59 C60 1.3900 . ?
C59 H59 0.9500 . ?
C60 C61 1.3900 . ?
C60 H60 0.9500 . ?
C61 H61 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
C25 N2 P1 N1 -172.49(15) . . . . ?
P2 N2 P1 N1 31.36(6) . . . . ?
C25 N2 P1 C49 96.47(15) . . . . ?
P2 N2 P1 C49 -59.68(7) . . . . ?
C25 N2 P1 P2 156.14(18) . . . . ?
C1 N1 P1 N2 -174.83(13) . . . . ?
P2 N1 P1 N2 -31.16(6) . . . . ?
C1 N1 P1 C49 -85.10(13) . . . . ?
P2 N1 P1 C49 58.57(6) . . . . ?
C1 N1 P1 P2 -143.67(15) . . . . ?
C49 O1 P2 N2 -35.92(10) . . . . ?
C49 O1 P2 N1 44.46(10) . . . . ?
C49 O1 P2 P1 3.21(8) . . . . ?
C25 N2 P2 O1 -96.86(13) . . . . ?
P1 N2 P2 O1 62.06(6) . . . . ?
C25 N2 P2 N1 169.18(13) . . . . ?
P1 N2 P2 N1 -31.91(6) . . . . ?
C25 N2 P2 P1 -158.92(15) . . . . ?
C1 N1 P2 O1 78.03(13) . . . . ?
P1 N1 P2 O1 -64.65(6) . . . . ?
C1 N1 P2 N2 173.85(13) . . . . ?
P1 N1 P2 N2 31.16(6) . . . . ?
C1 N1 P2 P1 142.68(15) . . . . ?
P2 N1 C1 C2 -166.86(11) . . . . ?
P1 N1 C1 C2 -36.60(19) . . . . ?
P2 N1 C1 C6 17.0(2) . . . . ?
P1 N1 C1 C6 147.22(12) . . . . ?
N1 C1 C2 C3 178.15(14) . . . . ?
C6 C1 C2 C3 -5.6(2) . . . . ?
N1 C1 C2 C7 -3.7(2) . . . . ?
C6 C1 C2 C7 172.57(13) . . . . ?
C1 C2 C3 C4 1.8(2) . . . . ?
C7 C2 C3 C4 -176.37(15) . . . . ?
C2 C3 C4 C5 2.2(3) . . . . ?
C3 C4 C5 C6 -2.4(3) . . . . ?
C4 C5 C6 C1 -1.4(2) . . . . ?
C4 C5 C6 C16 172.20(16) . . . . ?
N1 C1 C6 C5 -178.46(14) . . . . ?
C2 C1 C6 C5 5.4(2) . . . . ?
N1 C1 C6 C16 8.3(2) . . . . ?
C2 C1 C6 C16 -167.93(14) . . . . ?
C3 C2 C7 C12 -66.7(2) . . . . ?
C1 C2 C7 C12 115.12(16) . . . . ?
C3 C2 C7 C8 112.18(17) . . . . ?
C1 C2 C7 C8 -65.97(19) . . . . ?
C12 C7 C8 C9 -4.5(2) . . . . ?
C2 C7 C8 C9 176.61(13) . . . . ?
C12 C7 C8 C13 174.54(14) . . . . ?
C2 C7 C8 C13 -4.4(2) . . . . ?
C7 C8 C9 C10 1.3(2) . . . . ?
C13 C8 C9 C10 -177.76(15) . . . . ?
C8 C9 C10 C11 2.0(2) . . . . ?
C8 C9 C10 C14 -179.56(16) . . . . ?
C9 C10 C11 C12 -2.2(3) . . . . ?
C14 C10 C11 C12 179.41(16) . . . . ?
C10 C11 C12 C7 -1.0(2) . . . . ?
C10 C11 C12 C15 178.66(16) . . . . ?
C8 C7 C12 C11 4.3(2) . . . . ?
C2 C7 C12 C11 -176.78(14) . . . . ?
C8 C7 C12 C15 -175.31(14) . . . . ?
C2 C7 C12 C15 3.6(2) . . . . ?
C5 C6 C16 C17 79.1(2) . . . . ?
C1 C6 C16 C17 -107.52(18) . . . . ?
C5 C6 C16 C21 -97.15(18) . . . . ?
C1 C6 C16 C21 76.20(19) . . . . ?
C21 C16 C17 C18 -5.5(2) . . . . ?
C6 C16 C17 C18 178.28(14) . . . . ?
C21 C16 C17 C22 174.96(15) . . . . ?
C6 C16 C17 C22 -1.3(2) . . . . ?
C16 C17 C18 C19 1.9(3) . . . . ?
C22 C17 C18 C19 -178.55(16) . . . . ?
C17 C18 C19 C20 2.8(3) . . . . ?
C17 C18 C19 C23 -177.64(17) . . . . ?
C18 C19 C20 C21 -3.8(3) . . . . ?
C23 C19 C20 C21 176.58(17) . . . . ?
C19 C20 C21 C16 0.2(3) . . . . ?
C19 C20 C21 C24 -178.72(16) . . . . ?
C17 C16 C21 C20 4.5(2) . . . . ?
C6 C16 C21 C20 -179.05(14) . . . . ?
C17 C16 C21 C24 -176.56(15) . . . . ?
C6 C16 C21 C24 -0.1(2) . . . . ?
P2 N2 C25 C30 126.61(14) . . . . ?
P1 N2 C25 C30 -22.6(2) . . . . ?
P2 N2 C25 C26 -55.46(18) . . . . ?
P1 N2 C25 C26 155.29(12) . . . . ?
N2 C25 C26 C27 177.43(14) . . . . ?
C30 C25 C26 C27 -4.6(2) . . . . ?
N2 C25 C26 C31 -7.3(2) . . . . ?
C30 C25 C26 C31 170.67(14) . . . . ?
C25 C26 C27 C28 1.4(2) . . . . ?
C31 C26 C27 C28 -174.11(15) . . . . ?
C26 C27 C28 C29 2.1(3) . . . . ?
C27 C28 C29 C30 -2.4(3) . . . . ?
C28 C29 C30 C25 -0.8(2) . . . . ?
C28 C29 C30 C40 176.45(15) . . . . ?
N2 C25 C30 C29 -177.87(14) . . . . ?
C26 C25 C30 C29 4.3(2) . . . . ?
N2 C25 C30 C40 5.1(2) . . . . ?
C26 C25 C30 C40 -172.80(14) . . . . ?
C27 C26 C31 C36 -69.3(2) . . . . ?
C25 C26 C31 C36 115.35(17) . . . . ?
C27 C26 C31 C32 104.68(17) . . . . ?
C25 C26 C31 C32 -70.6(2) . . . . ?
C36 C31 C32 C33 -0.2(2) . . . . ?
C26 C31 C32 C33 -174.27(14) . . . . ?
C36 C31 C32 C37 178.32(14) . . . . ?
C26 C31 C32 C37 4.2(2) . . . . ?
C31 C32 C33 C34 1.7(2) . . . . ?
C37 C32 C33 C34 -176.88(16) . . . . ?
C32 C33 C34 C35 -1.6(3) . . . . ?
C32 C33 C34 C38 178.91(16) . . . . ?
C33 C34 C35 C36 0.1(3) . . . . ?
C38 C34 C35 C36 179.60(17) . . . . ?
C34 C35 C36 C31 1.3(2) . . . . ?
C34 C35 C36 C39 -176.08(16) . . . . ?
C32 C31 C36 C35 -1.2(2) . . . . ?
C26 C31 C36 C35 172.78(14) . . . . ?
C32 C31 C36 C39 176.06(15) . . . . ?
C26 C31 C36 C39 -9.9(2) . . . . ?
C29 C30 C40 C45 -103.81(17) . . . . ?
C25 C30 C40 C45 73.3(2) . . . . ?
C29 C30 C40 C41 72.26(19) . . . . ?
C25 C30 C40 C41 -110.66(17) . . . . ?
C45 C40 C41 C42 -3.5(2) . . . . ?
C30 C40 C41 C42 -179.52(14) . . . . ?
C45 C40 C41 C46 177.25(15) . . . . ?
C30 C40 C41 C46 1.2(2) . . . . ?
C40 C41 C42 C43 -0.8(2) . . . . ?
C46 C41 C42 C43 178.53(16) . . . . ?
C41 C42 C43 C44 3.5(3) . . . . ?
C41 C42 C43 C47 -175.00(17) . . . . ?
C42 C43 C44 C45 -2.0(3) . . . . ?
C47 C43 C44 C45 176.48(17) . . . . ?
C43 C44 C45 C40 -2.1(2) . . . . ?
C43 C44 C45 C48 175.04(15) . . . . ?
C41 C40 C45 C44 4.9(2) . . . . ?
C30 C40 C45 C44 -179.06(14) . . . . ?
C41 C40 C45 C48 -172.24(14) . . . . ?
C30 C40 C45 C48 3.8(2) . . . . ?
P2 O1 C49 C50 -132.01(11) . . . . ?
P2 O1 C49 P1 -4.21(11) . . . . ?
O1 C49 C50 C51 -149.43(14) . . . . ?
P1 C49 C50 C51 89.84(16) . . . . ?
O1 C49 C50 C55 30.8(2) . . . . ?
P1 C49 C50 C55 -89.89(17) . . . . ?
C55 C50 C51 C52 -2.1(3) . . . . ?
C49 C50 C51 C52 178.11(16) . . . . ?
C50 C51 C52 C53 -0.4(3) . . . . ?
C51 C52 C53 C54 2.2(3) . . . . ?
C52 C53 C54 C55 -1.5(3) . . . . ?
C51 C50 C55 C54 2.8(2) . . . . ?
C49 C50 C55 C54 -177.42(15) . . . . ?
C53 C54 C55 C50 -1.1(3) . . . . ?
C61 C56 C57 C58 0.0 . . . . ?
C56 C57 C58 C59 0.0 . . . . ?
C57 C58 C59 C60 0.0 . . . . ?
C58 C59 C60 C61 0.0 . . . . ?
C59 C60 C61 C56 0.0 . . . . ?
C57 C56 C61 C60 0.0 . . . . ?
