#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/54/7035438.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_7035438
loop_
_publ_author_name
'Laborde, Coralie'
'Wei, Muh-Mei'
'van der Lee, Arie'
'Deydier, Eric'
'Daran, Jean-Claude'
'Volle, Jean-Noël'
'Poli, Rinaldo'
'Pirat, Jean-Luc'
'Manoury, Eric'
'Virieux, David'
_publ_section_title
;
 Double [3 + 2]-dimerisation cascade synthesis of
 bis(triazolyl)bisphosphanes, a new scaffold for bidentate bisphosphanes.
;
_journal_issue                   28
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              12539
_journal_page_last               12545
_journal_paper_doi               10.1039/c5dt02197a
_journal_volume                  44
_journal_year                    2015
_chemical_formula_moiety         '2(C42 H34 N6 O2 P2), C2 H3 N'
_chemical_formula_sum            'C86 H71 N13 O4 P4'
_chemical_formula_weight         1474.44
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_update_record
;
2014-10-31 deposited with the CCDC.
2015-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.6830(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.8008(2)
_cell_length_b                   16.6628(3)
_cell_length_c                   17.8668(3)
_cell_measurement_reflns_used    31838
_cell_measurement_temperature    175
_cell_measurement_theta_max      28.9856
_cell_measurement_theta_min      2.8568
_cell_volume                     3756.65(11)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      175
_diffrn_detector_area_resol_mean 8.4205
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_details
;
  1 omega    3.00  101.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       19.4101   77.0000  120.0000 98

  2 omega  -14.00  101.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       19.4101   77.0000 -120.0000 115

  3 omega  -19.00   85.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       19.4101   77.0000   30.0000 104

  4 omega  -57.00   69.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5351   77.0000  120.0000 126

  5 omega  -61.00   50.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5351   77.0000    0.0000 111

  6 omega  -61.00   50.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5351   77.0000 -120.0000 111

  7 omega   34.00  118.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       19.4101  179.0000   30.0000 84

  8 omega  -59.00  -24.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5351   38.0000   90.0000 35

  9 omega  -59.00   67.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5351   38.0000 -150.0000 126

;
_diffrn_measurement_device       Serial
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0124929000
_diffrn_orient_matrix_UB_12      0.0381873000
_diffrn_orient_matrix_UB_13      -0.0166372000
_diffrn_orient_matrix_UB_21      0.0259241000
_diffrn_orient_matrix_UB_22      -0.0105436000
_diffrn_orient_matrix_UB_23      -0.0307026000
_diffrn_orient_matrix_UB_31      -0.0483052000
_diffrn_orient_matrix_UB_32      -0.0155360000
_diffrn_orient_matrix_UB_33      -0.0200684000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.023
_diffrn_reflns_av_sigmaI/netI    0.0559
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            64742
_diffrn_reflns_theta_full        26.726
_diffrn_reflns_theta_max         29.050
_diffrn_reflns_theta_min         2.863
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1540
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.49
_refine_diff_density_min         -0.67
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.8507
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     476
_refine_ls_number_reflns         9225
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.0008743
_refine_ls_shift/su_mean         0.0000359
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.10P)² + 3.94P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1425
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1425
_reflns_limit_h_max              16
_reflns_limit_h_min              -17
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                7926
_reflns_number_total             9225
_reflns_threshold_expression     I>2.0σ(I)
_oxford_refine_ls_scale          3.16(3)
_cod_data_source_file            c5dt02197a2.cif
_cod_data_source_block           8.1
_cod_depositor_comments
'Adding full bibliography for 7035438--7035443.cif.'
_cod_original_cell_volume        3756.64(11)
_cod_original_sg_symbol_H-M      'P 21/n '
_cod_database_code               7035438
#BEGIN Tags that were not found in dictionaries:
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE P(1,X'S, U'S) UNTIL C(20) 
CONT  C(21,X'S, U'S) UNTIL C(26) 
CONT  C(27,X'S, U'S) UNTIL C(33) 
CONT  C(34,X'S, U'S) UNTIL C(40) 
CONT  C(41,X'S, U'S) UNTIL C(46) 
CONT  C(47,X'S, U'S) UNTIL C(52) 
CONT  C(53,X'S) UNTIL N(54) 
EQUIV C(53,U[ISO]) N(54,U[ISO]) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 272,X'S) H   ( 271,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) 
RIDE C   (  34,X'S) H   ( 342,X'S) H   ( 341,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) 
RIDE C   (  40,X'S) H   ( 401,X'S) 
RIDE C   (  42,X'S) H   ( 421,X'S) 
RIDE C   (  43,X'S) H   ( 431,X'S) 
RIDE C   (  44,X'S) H   ( 441,X'S) 
RIDE C   (  45,X'S) H   ( 451,X'S) 
RIDE C   (  46,X'S) H   ( 461,X'S) 
RIDE C   (  48,X'S) H   ( 481,X'S) 
RIDE C   (  49,X'S) H   ( 491,X'S) 
RIDE C   (  50,X'S) H   ( 501,X'S) 
RIDE C   (  51,X'S) H   ( 511,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) 
RIDE C   (  53,X'S) H   ( 531,X'S) H   ( 532,X'S) H   ( 533,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
DIST  1.08 , .01 =      C(53) TO N(54) 
DIST  1.47 , .01 =      C(53) TO C(53,-1,1,1,1) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,-y+1/2,z+1/2
-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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
P1 P 0.48697(3) 0.66183(2) 0.29645(2) 0.0206 1.0000 Uani .
O2 O 0.59269(9) 0.69755(7) 0.29319(7) 0.0250 1.0000 Uani .
C3 C 0.38623(12) 0.72613(9) 0.24610(9) 0.0208 1.0000 Uani .
N4 N 0.27921(11) 0.71586(9) 0.24064(9) 0.0270 1.0000 Uani .
N5 N 0.23094(11) 0.77880(9) 0.20772(9) 0.0280 1.0000 Uani .
N6 N 0.30575(11) 0.83023(8) 0.19184(8) 0.0223 1.0000 Uani .
C7 C 0.40390(12) 0.79973(9) 0.21469(8) 0.0192 1.0000 Uani .
C8 C 0.50267(12) 0.83923(9) 0.20498(8) 0.0192 1.0000 Uani .
N9 N 0.56466(11) 0.81154(8) 0.15590(8) 0.0219 1.0000 Uani .
N10 N 0.65510(12) 0.85402(9) 0.16180(8) 0.0266 1.0000 Uani .
N11 N 0.65213(12) 0.90950(9) 0.21336(8) 0.0263 1.0000 Uani .
C12 C 0.55909(13) 0.90239(10) 0.24125(9) 0.0212 1.0000 Uani .
P13 P 0.52744(3) 0.96110(3) 0.31884(2) 0.0218 1.0000 Uani .
O14 O 0.41441(10) 0.95052(8) 0.32668(7) 0.0302 1.0000 Uani .
C15 C 0.56194(13) 1.06335(10) 0.30239(9) 0.0229 1.0000 Uani .
C16 C 0.66417(14) 1.08319(11) 0.29018(11) 0.0290 1.0000 Uani .
C17 C 0.69025(15) 1.16238(11) 0.27897(11) 0.0319 1.0000 Uani .
C18 C 0.61599(16) 1.22233(11) 0.28275(11) 0.0329 1.0000 Uani .
C19 C 0.51527(15) 1.20355(11) 0.29571(11) 0.0324 1.0000 Uani .
C20 C 0.48738(14) 1.12386(11) 0.30480(10) 0.0281 1.0000 Uani .
H201 H 0.4174 1.1113 0.3144 0.0323 1.0000 Uiso R
H191 H 0.4637 1.2450 0.2967 0.0367 1.0000 Uiso R
H181 H 0.6334 1.2782 0.2778 0.0396 1.0000 Uiso R
H171 H 0.7561 1.1742 0.2671 0.0380 1.0000 Uiso R
H161 H 0.7176 1.0418 0.2865 0.0336 1.0000 Uiso R
C21 C 0.62157(14) 0.92985(10) 0.40040(10) 0.0258 1.0000 Uani .
C22 C 0.68918(16) 0.86460(12) 0.39983(11) 0.0343 1.0000 Uani .
C23 C 0.7569(2) 0.84275(14) 0.46620(13) 0.0464 1.0000 Uani .
C24 C 0.7550(2) 0.88420(16) 0.53289(13) 0.0499 1.0000 Uani .
C25 C 0.6876(2) 0.94871(16) 0.53390(12) 0.0482 1.0000 Uani .
C26 C 0.62222(17) 0.97217(13) 0.46778(11) 0.0378 1.0000 Uani .
H261 H 0.5769 1.0161 0.4675 0.0441 1.0000 Uiso R
H251 H 0.6836 0.9779 0.5786 0.0566 1.0000 Uiso R
H241 H 0.7978 0.8685 0.5779 0.0576 1.0000 Uiso R
H231 H 0.8017 0.7979 0.4663 0.0545 1.0000 Uiso R
H221 H 0.6855 0.8343 0.3551 0.0410 1.0000 Uiso R
C27 C 0.54863(15) 0.74049(10) 0.10632(10) 0.0289 1.0000 Uani .
C28 C 0.57834(14) 0.75676(11) 0.02955(10) 0.0276 1.0000 Uani .
C29 C 0.51093(16) 0.80245(12) -0.02281(11) 0.0337 1.0000 Uani .
C30 C 0.5356(2) 0.81913(14) -0.09386(12) 0.0428 1.0000 Uani .
C31 C 0.62912(19) 0.79018(16) -0.11207(12) 0.0480 1.0000 Uani .
C32 C 0.69614(18) 0.74526(19) -0.06138(14) 0.0554 1.0000 Uani .
C33 C 0.67146(17) 0.72824(17) 0.01041(12) 0.0456 1.0000 Uani .
H331 H 0.7171 0.6971 0.0452 0.0542 1.0000 Uiso R
H321 H 0.7582 0.7231 -0.0746 0.0642 1.0000 Uiso R
H311 H 0.6483 0.8021 -0.1610 0.0570 1.0000 Uiso R
H301 H 0.4856 0.8519 -0.1299 0.0504 1.0000 Uiso R
H291 H 0.4424 0.8232 -0.0105 0.0403 1.0000 Uiso R
H272 H 0.4730 0.7271 0.1003 0.0340 1.0000 Uiso R
H271 H 0.5933 0.6961 0.1327 0.0338 1.0000 Uiso R
C34 C 0.27404(14) 0.90953(10) 0.15986(10) 0.0270 1.0000 Uani .
C35 C 0.28922(13) 0.92000(10) 0.07877(10) 0.0236 1.0000 Uani .
C36 C 0.23681(14) 0.87090(11) 0.02183(10) 0.0301 1.0000 Uani .
C37 C 0.24493(16) 0.88523(13) -0.05368(11) 0.0354 1.0000 Uani .
C38 C 0.30455(17) 0.94897(13) -0.07223(11) 0.0385 1.0000 Uani .
C39 C 0.35720(18) 0.99768(13) -0.01607(12) 0.0408 1.0000 Uani .
C40 C 0.35025(16) 0.98313(12) 0.05934(11) 0.0343 1.0000 Uani .
H401 H 0.3918 1.0163 0.0976 0.0410 1.0000 Uiso R
H391 H 0.3994 1.0391 -0.0295 0.0486 1.0000 Uiso R
H381 H 0.3095 0.9595 -0.1236 0.0442 1.0000 Uiso R
H371 H 0.2109 0.8503 -0.0922 0.0425 1.0000 Uiso R
H361 H 0.1959 0.8273 0.0340 0.0363 1.0000 Uiso R
H342 H 0.3144 0.9480 0.1913 0.0322 1.0000 Uiso R
H341 H 0.1992 0.9131 0.1644 0.0313 1.0000 Uiso R
C41 C 0.47110(13) 0.56355(10) 0.25486(10) 0.0245 1.0000 Uani .
C42 C 0.37382(14) 0.52982(11) 0.22335(10) 0.0295 1.0000 Uani .
C43 C 0.37013(17) 0.45311(12) 0.19273(12) 0.0373 1.0000 Uani .
C44 C 0.4629(2) 0.41023(12) 0.19339(14) 0.0455 1.0000 Uani .
C45 C 0.55980(19) 0.44308(13) 0.22466(16) 0.0482 1.0000 Uani .
C46 C 0.56405(16) 0.51966(11) 0.25567(13) 0.0362 1.0000 Uani .
H461 H 0.6292 0.5428 0.2759 0.0416 1.0000 Uiso R
H451 H 0.6207 0.4141 0.2269 0.0558 1.0000 Uiso R
H441 H 0.4591 0.3599 0.1743 0.0528 1.0000 Uiso R
H431 H 0.3069 0.4316 0.1698 0.0424 1.0000 Uiso R
H421 H 0.3141 0.5591 0.2218 0.0326 1.0000 Uiso R
C47 C 0.45861(13) 0.65532(10) 0.39161(9) 0.0243 1.0000 Uani .
C48 C 0.42232(18) 0.58616(13) 0.42173(11) 0.0385 1.0000 Uani .
C49 C 0.4065(2) 0.58483(15) 0.49710(12) 0.0472 1.0000 Uani .
C50 C 0.42777(19) 0.65177(15) 0.54191(12) 0.0433 1.0000 Uani .
C51 C 0.46499(19) 0.72107(14) 0.51278(12) 0.0426 1.0000 Uani .
C52 C 0.47985(16) 0.72295(12) 0.43742(11) 0.0345 1.0000 Uani .
H521 H 0.5056 0.7705 0.4190 0.0413 1.0000 Uiso R
H511 H 0.4745 0.7678 0.5417 0.0528 1.0000 Uiso R
H501 H 0.4167 0.6499 0.5931 0.0494 1.0000 Uiso R
H491 H 0.3807 0.5379 0.5199 0.0555 1.0000 Uiso R
H481 H 0.4107 0.5406 0.3911 0.0462 1.0000 Uiso R
C53 C 0.5343(4) 0.5252(3) 0.0274(3) 0.1155(14) 1.0000 Uiso D
N54 N 0.5923(6) 0.5556(5) 0.0724(5) 0.1155(14) 0.5000 Uiso D
H531 H 0.5542 0.4930 0.0714 0.0600 0.5000 Uiso R
H532 H 0.5958 0.5402 0.0076 0.0600 0.5000 Uiso R
H533 H 0.4989 0.5720 0.0404 0.0600 0.5000 Uiso R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O2 . P1 C3 108.82(7) yes
O2 . P1 C41 112.88(8) yes
C3 . P1 C41 108.35(8) yes
O2 . P1 C47 112.96(7) yes
C3 . P1 C47 105.48(7) yes
C41 . P1 C47 108.00(8) yes
P1 . C3 N4 125.94(12) yes
P1 . C3 C7 125.39(12) yes
N4 . C3 C7 108.19(14) yes
C3 . N4 N5 108.91(14) yes
N4 . N5 N6 107.80(13) yes
N5 . N6 C7 110.71(13) yes
N5 . N6 C34 119.54(14) yes
C7 . N6 C34 129.55(14) yes
C3 . C7 N6 104.39(13) yes
C3 . C7 C8 130.64(14) yes
N6 . C7 C8 124.97(14) yes
C7 . C8 N9 122.33(14) yes
C7 . C8 C12 133.22(14) yes
N9 . C8 C12 104.27(13) yes
C8 . N9 N10 111.04(13) yes
C8 . N9 C27 128.61(14) yes
N10 . N9 C27 120.07(13) yes
N9 . N10 N11 107.45(13) yes
N10 . N11 C12 108.92(13) yes
C8 . C12 N11 108.31(14) yes
C8 . C12 P13 127.68(12) yes
N11 . C12 P13 123.73(12) yes
C12 . P13 O14 110.92(7) yes
C12 . P13 C15 107.24(7) yes
O14 . P13 C15 113.43(8) yes
C12 . P13 C21 105.03(8) yes
O14 . P13 C21 114.69(8) yes
C15 . P13 C21 104.87(8) yes
P13 . C15 C16 120.71(13) yes
P13 . C15 C20 119.50(13) yes
C16 . C15 C20 119.74(16) yes
C15 . C16 C17 120.11(16) yes
C15 . C16 H161 121.6 no
C17 . C16 H161 118.2 no
C16 . C17 C18 119.69(17) yes
C16 . C17 H171 119.2 no
C18 . C17 H171 121.1 no
C17 . C18 C19 120.69(17) yes
C17 . C18 H181 121.3 no
C19 . C18 H181 118.0 no
C18 . C19 C20 119.99(17) yes
C18 . C19 H191 120.3 no
C20 . C19 H191 119.7 no
C15 . C20 C19 119.75(16) yes
C15 . C20 H201 120.7 no
C19 . C20 H201 119.5 no
P13 . C21 C22 123.47(14) yes
P13 . C21 C26 117.23(14) yes
C22 . C21 C26 119.25(17) yes
C21 . C22 C23 119.77(18) yes
C21 . C22 H221 119.0 no
C23 . C22 H221 121.1 no
C22 . C23 C24 120.3(2) yes
C22 . C23 H231 120.0 no
C24 . C23 H231 119.6 no
C23 . C24 C25 120.1(2) yes
C23 . C24 H241 120.8 no
C25 . C24 H241 119.0 no
C24 . C25 C26 119.9(2) yes
C24 . C25 H251 122.4 no
C26 . C25 H251 117.8 no
C21 . C26 C25 120.6(2) yes
C21 . C26 H261 118.6 no
C25 . C26 H261 120.8 no
N9 . C27 C28 111.82(14) yes
N9 . C27 H272 106.5 no
C28 . C27 H272 109.6 no
N9 . C27 H271 107.5 no
C28 . C27 H271 110.4 no
H272 . C27 H271 110.9 no
C27 . C28 C29 119.22(16) yes
C27 . C28 C33 121.62(18) yes
C29 . C28 C33 119.16(18) yes
C28 . C29 C30 121.01(19) yes
C28 . C29 H291 120.6 no
C30 . C29 H291 118.4 no
C29 . C30 C31 119.1(2) yes
C29 . C30 H301 118.9 no
C31 . C30 H301 122.1 no
C30 . C31 C32 120.7(2) yes
C30 . C31 H311 120.2 no
C32 . C31 H311 119.1 no
C31 . C32 C33 120.4(2) yes
C31 . C32 H321 120.8 no
C33 . C32 H321 118.7 no
C32 . C33 C28 119.7(2) yes
C32 . C33 H331 120.6 no
C28 . C33 H331 119.7 no
N6 . C34 C35 114.02(14) yes
N6 . C34 H342 106.9 no
C35 . C34 H342 110.3 no
N6 . C34 H341 103.5 no
C35 . C34 H341 111.1 no
H342 . C34 H341 110.8 no
C34 . C35 C36 120.86(16) yes
C34 . C35 C40 119.86(16) yes
C36 . C35 C40 119.11(16) yes
C35 . C36 C37 120.27(17) yes
C35 . C36 H361 120.3 no
C37 . C36 H361 119.4 no
C36 . C37 C38 119.96(18) yes
C36 . C37 H371 119.9 no
C38 . C37 H371 120.1 no
C37 . C38 C39 120.11(18) yes
C37 . C38 H381 120.4 no
C39 . C38 H381 119.5 no
C38 . C39 C40 120.13(18) yes
C38 . C39 H391 118.9 no
C40 . C39 H391 120.9 no
C35 . C40 C39 120.41(18) yes
C35 . C40 H401 121.5 no
C39 . C40 H401 118.1 no
P1 . C41 C42 124.43(14) yes
P1 . C41 C46 115.92(14) yes
C42 . C41 C46 119.66(17) yes
C41 . C42 C43 119.91(18) yes
C41 . C42 H421 119.2 no
C43 . C42 H421 120.9 no
C42 . C43 C44 119.99(19) yes
C42 . C43 H431 120.3 no
C44 . C43 H431 119.6 no
C43 . C44 C45 120.56(19) yes
C43 . C44 H441 119.0 no
C45 . C44 H441 120.4 no
C44 . C45 C46 119.8(2) yes
C44 . C45 H451 120.6 no
C46 . C45 H451 119.6 no
C41 . C46 C45 120.12(19) yes
C41 . C46 H461 119.4 no
C45 . C46 H461 120.4 no
P1 . C47 C48 123.44(14) yes
P1 . C47 C52 117.12(13) yes
C48 . C47 C52 119.36(17) yes
C47 . C48 C49 120.05(19) yes
C47 . C48 H481 118.7 no
C49 . C48 H481 121.3 no
C48 . C49 C50 120.2(2) yes
C48 . C49 H491 122.4 no
C50 . C49 H491 117.4 no
C49 . C50 C51 120.36(19) yes
C49 . C50 H501 119.2 no
C51 . C50 H501 120.5 no
C50 . C51 C52 119.6(2) yes
C50 . C51 H511 120.7 no
C52 . C51 H511 119.4 no
C47 . C52 C51 120.37(18) yes
C47 . C52 H521 121.5 no
C51 . C52 H521 118.1 no
C53 2_665 C53 N54 171.9(9) yes
C53 2_665 C53 H531 106.1 no
N54 . C53 H531 66.9 no
C53 2_665 C53 H532 110.0 no
N54 . C53 H532 69.9 no
H531 . C53 H532 109.5 no
C53 2_665 C53 H533 112.2 no
N54 . C53 H533 74.9 no
H531 . C53 H533 109.5 no
H532 . C53 H533 109.5 no
C53 . N54 H531 49.5 no
C53 . N54 H532 48.4 no
H531 . N54 H532 82.9 no
C53 . N54 H533 46.5 no
H531 . N54 H533 79.8 no
H532 . N54 H533 78.2 no
N54 . H531 C53 63.6 no
N54 . H532 C53 61.7 no
C53 . H533 N54 58.7 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O2 . 1.4885(12) yes
P1 C3 . 1.7971(16) yes
P1 C41 . 1.7957(18) yes
P1 C47 . 1.8006(17) yes
C3 N4 . 1.368(2) yes
C3 C7 . 1.383(2) yes
N4 N5 . 1.306(2) yes
N5 N6 . 1.3503(19) yes
N6 C7 . 1.353(2) yes
N6 C34 . 1.469(2) yes
C7 C8 . 1.461(2) yes
C8 N9 . 1.359(2) yes
C8 C12 . 1.375(2) yes
N9 N10 . 1.3458(19) yes
N9 C27 . 1.472(2) yes
N10 N11 . 1.310(2) yes
N11 C12 . 1.371(2) yes
C12 P13 . 1.7977(16) yes
P13 O14 . 1.4874(12) yes
P13 C15 . 1.7965(17) yes
P13 C21 . 1.8044(18) yes
C15 C16 . 1.402(2) yes
C15 C20 . 1.394(2) yes
C16 C17 . 1.384(3) yes
C16 H161 . 0.981 no
C17 C18 . 1.388(3) yes
C17 H171 . 0.924 no
C18 C19 . 1.384(3) yes
C18 H181 . 0.966 no
C19 C20 . 1.392(3) yes
C19 H191 . 0.958 no
C20 H201 . 0.963 no
C21 C22 . 1.391(3) yes
C21 C26 . 1.394(2) yes
C22 C23 . 1.394(3) yes
C22 H221 . 0.940 no
C23 C24 . 1.381(3) yes
C23 H231 . 0.942 no
C24 C25 . 1.381(3) yes
C24 H241 . 0.930 no
C25 C26 . 1.384(3) yes
C25 H251 . 0.944 no
C26 H261 . 0.934 no
C27 C28 . 1.508(2) yes
C27 H272 . 0.982 no
C27 H271 . 1.003 no
C28 C29 . 1.388(3) yes
C28 C33 . 1.379(3) yes
C29 C30 . 1.387(3) yes
C29 H291 . 1.001 no
C30 C31 . 1.379(3) yes
C30 H301 . 0.992 no
C31 C32 . 1.362(4) yes
C31 H311 . 0.967 no
C32 C33 . 1.401(3) yes
C32 H321 . 0.942 no
C33 H331 . 0.935 no
C34 C35 . 1.504(2) yes
C34 H342 . 0.946 no
C34 H341 . 0.977 no
C35 C36 . 1.387(2) yes
C35 C40 . 1.389(2) yes
C36 C37 . 1.391(3) yes
C36 H361 . 0.942 no
C37 C38 . 1.380(3) yes
C37 H371 . 0.949 no
C38 C39 . 1.376(3) yes
C38 H381 . 0.947 no
C39 C40 . 1.386(3) yes
C39 H391 . 0.933 no
C40 H401 . 0.966 no
C41 C42 . 1.396(2) yes
C41 C46 . 1.395(3) yes
C42 C43 . 1.388(3) yes
C42 H421 . 0.903 no
C43 C44 . 1.384(3) yes
C43 H431 . 0.917 no
C44 C45 . 1.385(3) yes
C44 H441 . 0.903 no
C45 C46 . 1.389(3) yes
C45 H451 . 0.911 no
C46 H461 . 0.934 no
C47 C48 . 1.385(2) yes
C47 C52 . 1.392(3) yes
C48 C49 . 1.395(3) yes
C48 H481 . 0.933 no
C49 C50 . 1.373(3) yes
C49 H491 . 0.965 no
C50 C51 . 1.384(3) yes
C50 H501 . 0.950 no
C51 C52 . 1.391(3) yes
C51 H511 . 0.931 no
C52 H521 . 0.939 no
C53 C53 2_665 1.465(7) yes
C53 N54 . 1.119(7) yes
C53 H531 . 0.950 no
C53 H532 . 0.950 no
C53 H533 . 0.950 no
N54 H531 . 1.149 no
N54 H532 . 1.193 no
N54 H533 . 1.264 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C19 H191 N5 4_555 146 0.96 2.54 3.383(3) yes
C17 H171 O2 4_655 167 0.92 2.40 3.306(3) yes
C25 H251 O14 2_676 154 0.94 2.56 3.438(3) yes
C27 H271 N54 . 121 1.00 2.58 3.208(3) yes
C37 H371 O2 3_464 161 0.95 2.46 3.375(3) yes
C34 H342 O14 . 136 0.95 2.54 3.283(3) yes
