#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:37:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178434 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/55/4025502.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_4025502
loop_
_publ_author_name
'Daniel J. St-Cyr'
'Marie S. T. Morin'
'Francine Bélanger-Gariépy'
'Bruce A. Arndtsen'
'Elizabeth H. Krenske'
'K. N. Houk'
_publ_contact_author_address
;
      University of McGill
      Department of Chemistry
      Otto Maass Chemistry Building
      801 Sherbrooke St. West
      Montréal, Québec
      Canada H3A 2K6
;
_publ_contact_author_email       bruce.arndtsen@mcgill.ca
_publ_contact_author_fax         '+1 514 398 3797'
_publ_contact_author_name        'Dr. Bruce Arndtsen'
_publ_contact_author_phone       '+1 514 398 6903'
_publ_section_title
;
 Phospha-Münchnones: Electronic Structures and 1,3-Dipolar
 Cycloadditions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4261
_journal_page_last               4273
_journal_paper_doi               10.1021/jo1008383
_journal_volume                  75
_journal_year                    2010
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C27 H22 N O3 P, C6 H6'
_chemical_formula_sum            'C33 H28 N O3 P'
_chemical_formula_weight         517.53
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 123.410(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.216(5)
_cell_length_b                   10.1336(14)
_cell_length_c                   20.831(3)
_cell_measurement_reflns_used    5076
_cell_measurement_temperature    150
_cell_measurement_theta_max      71.94
_cell_measurement_theta_min      3.50
_cell_volume                     5324.4(14)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_data_collection       'APEX2 v2.1-0 (Bruker AXS, 2006a)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2004)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker Smart 6000'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Montel 200 optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.065
_diffrn_reflns_av_sigmaI/netI    0.1149
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            35907
_diffrn_reflns_theta_full        72.83
_diffrn_reflns_theta_max         72.83
_diffrn_reflns_theta_min         3.50
_diffrn_standards_decay_%        3.00
_diffrn_standards_interval_time  900
_diffrn_standards_number         215
_exptl_absorpt_coefficient_mu    1.194
_exptl_absorpt_correction_T_max  0.9534
_exptl_absorpt_correction_T_min  0.7302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2007)'
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.00067(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         5245
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1300
_refine_ls_R_factor_gt           0.0606
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0722P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1692
_reflns_number_gt                2847
_reflns_number_total             5245
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo1008383_si_003.cif
_cod_data_source_block           arst31
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_angle_publ_flag' value 'Y' changed to 'y'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (65
times).

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
the built-in table from CIF Core dictionary named 'cif_core.dic'
version 2.4.1 from 2010-06-29 (47 times).

'_geom_torsion_publ_flag'
value 'Y' changed to 'y' according to the built-in table from CIF
Core dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29
(91 time).

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        5324.5(13)
_cod_database_code               4025502
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.65385(3) 0.12811(7) 0.65385(4) 0.0351(3) Uani 1 1 d . . .
O1 O 0.66164(7) 0.15661(18) 0.57883(10) 0.0352(5) Uani 1 1 d . . .
O2 O 0.61413(7) 0.26018(17) 0.62852(10) 0.0351(5) Uani 1 1 d . . .
O3 O 0.64600(8) 0.11239(17) 0.73260(11) 0.0361(5) Uani 1 1 d . . .
N1 N 0.73273(10) 0.1140(2) 0.79741(13) 0.0356(6) Uani 1 1 d . . .
C1 C 0.60985(11) -0.0120(3) 0.60533(17) 0.0339(7) Uani 1 1 d . . .
C2 C 0.61184(13) -0.1236(3) 0.64625(18) 0.0436(8) Uani 1 1 d . . .
H2 H 0.6375 -0.1283 0.7000 0.052 Uiso 1 1 calc R . .
C3 C 0.57698(15) -0.2272(3) 0.6097(2) 0.0509(9) Uani 1 1 d . . .
H3 H 0.5792 -0.3025 0.6384 0.061 Uiso 1 1 calc R . .
C4 C 0.53898(13) -0.2222(3) 0.5318(2) 0.0469(9) Uani 1 1 d . . .
H4 H 0.5141 -0.2919 0.5073 0.056 Uiso 1 1 calc R . .
C5 C 0.53753(13) -0.1148(3) 0.49005(19) 0.0463(8) Uani 1 1 d . . .
H5 H 0.5123 -0.1120 0.4361 0.056 Uiso 1 1 calc R . .
C6 C 0.57272(12) -0.0106(3) 0.52647(17) 0.0407(8) Uani 1 1 d . . .
H6 H 0.5713 0.0627 0.4970 0.049 Uiso 1 1 calc R . .
C7 C 0.64011(12) 0.2749(3) 0.54355(16) 0.0348(7) Uani 1 1 d . . .
C8 C 0.61192(12) 0.3334(3) 0.57063(16) 0.0356(7) Uani 1 1 d . . .
C9 C 0.58586(12) 0.4518(3) 0.54185(16) 0.0408(8) Uani 1 1 d . . .
H9 H 0.5663 0.4909 0.5603 0.049 Uiso 1 1 calc R . .
C10 C 0.58939(13) 0.5117(3) 0.48470(17) 0.0460(9) Uani 1 1 d . . .
H10 H 0.5718 0.5933 0.4635 0.055 Uiso 1 1 calc R . .
C11 C 0.61787(13) 0.4551(3) 0.45838(17) 0.0463(8) Uani 1 1 d . . .
H11 H 0.6198 0.4984 0.4196 0.056 Uiso 1 1 calc R . .
C12 C 0.64395(12) 0.3351(3) 0.48772(16) 0.0411(8) Uani 1 1 d . . .
H12 H 0.6638 0.2962 0.4697 0.049 Uiso 1 1 calc R . .
C13 C 0.69061(13) 0.1108(3) 0.80105(17) 0.0349(7) Uani 1 1 d . . .
C14 C 0.72056(12) 0.1229(3) 0.72058(16) 0.0345(7) Uani 1 1 d . . .
C15 C 0.78738(12) 0.1353(3) 0.86403(17) 0.0476(8) Uani 1 1 d . . .
H15A H 0.7865 0.1685 0.9075 0.071 Uiso 1 1 calc R . .
H15B H 0.8051 0.2000 0.8505 0.071 Uiso 1 1 calc R . .
H15C H 0.8069 0.0517 0.8783 0.071 Uiso 1 1 calc R . .
C16 C 0.68853(12) 0.1075(3) 0.86953(16) 0.0340(7) Uani 1 1 d . . .
C17 C 0.64600(12) 0.1679(3) 0.86577(17) 0.0407(8) Uani 1 1 d . . .
H17 H 0.6200 0.2124 0.8201 0.049 Uiso 1 1 calc R . .
C18 C 0.64120(14) 0.1640(3) 0.92811(19) 0.0478(9) Uani 1 1 d . . .
H18 H 0.6124 0.2075 0.9255 0.057 Uiso 1 1 calc R . .
C19 C 0.67803(15) 0.0971(3) 0.99397(19) 0.0498(9) Uani 1 1 d . . .
H19 H 0.6743 0.0937 1.0363 0.060 Uiso 1 1 calc R . .
C20 C 0.72030(14) 0.0352(3) 0.99857(17) 0.0508(9) Uani 1 1 d . . .
H20 H 0.7457 -0.0106 1.0441 0.061 Uiso 1 1 calc R . .
C21 C 0.72572(13) 0.0398(3) 0.93685(17) 0.0445(8) Uani 1 1 d . . .
H21 H 0.7548 -0.0033 0.9401 0.053 Uiso 1 1 calc R . .
C22 C 0.76457(12) 0.1155(3) 0.70937(16) 0.0336(7) Uani 1 1 d . . .
C23 C 0.79812(12) 0.0062(3) 0.73421(16) 0.0386(8) Uani 1 1 d . . .
H23 H 0.7914 -0.0657 0.7570 0.046 Uiso 1 1 calc R . .
C24 C 0.84099(13) -0.0012(3) 0.72680(17) 0.0447(8) Uani 1 1 d . . .
H24 H 0.8636 -0.0761 0.7453 0.054 Uiso 1 1 calc R . .
C25 C 0.85044(13) 0.1024(3) 0.69191(17) 0.0445(8) Uani 1 1 d . . .
H25 H 0.8795 0.0986 0.6862 0.053 Uiso 1 1 calc R . .
C26 C 0.81725(12) 0.2103(3) 0.66573(16) 0.0418(8) Uani 1 1 d . . .
H26 H 0.8232 0.2801 0.6410 0.050 Uiso 1 1 calc R . .
C27 C 0.77536(12) 0.2187(3) 0.67490(16) 0.0385(8) Uani 1 1 d . . .
H27 H 0.7536 0.2952 0.6577 0.046 Uiso 1 1 calc R . .
C31 C 0.4970(8) 0.2486(5) 0.7625(9) 0.064(6) Uani 0.50 1 d PG A -1
H31 H 0.4951 0.1570 0.7703 0.077 Uiso 0.50 1 calc PR A -1
C32 C 0.5149(6) 0.2908(7) 0.7171(7) 0.064(5) Uani 0.50 1 d PG A -1
H32 H 0.5252 0.2280 0.6939 0.076 Uiso 0.50 1 calc PR A -1
C33 C 0.5178(8) 0.4249(8) 0.7058(10) 0.062(4) Uani 0.50 1 d PG A -1
H33 H 0.5300 0.4537 0.6748 0.075 Uiso 0.50 1 calc PR A -1
C34 C 0.5027(10) 0.5168(6) 0.7399(13) 0.062(5) Uani 0.50 1 d PG A -1
H34 H 0.5047 0.6085 0.7321 0.075 Uiso 0.50 1 calc PR A -1
C35 C 0.4848(8) 0.4746(6) 0.7853(10) 0.058(5) Uani 0.50 1 d PG A -1
H35 H 0.4746 0.5375 0.8086 0.070 Uiso 0.50 1 calc PR A -1
C36 C 0.4820(8) 0.3405(6) 0.7966(8) 0.069(4) Uani 0.50 1 d PG A -1
H36 H 0.4698 0.3117 0.8276 0.082 Uiso 0.50 1 calc PR A -1
C41 C 0.54738(15) 0.8867(3) 0.8216(2) 0.0544(9) Uani 1 1 d . . .
H41 H 0.5799 0.8859 0.8706 0.065 Uiso 1 1 calc R . .
C42 C 0.54723(16) 0.8878(3) 0.7556(2) 0.0616(10) Uani 1 1 d . . .
H42 H 0.5799 0.8894 0.7590 0.074 Uiso 1 1 calc R . .
C43 C 0.50005(17) 0.8867(3) 0.6843(2) 0.0614(10) Uani 1 1 d . . .
H43 H 0.5005 0.8859 0.6390 0.074 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 P1 C14 . . . 126.90(12) y
O2 P1 O1 . . . 90.71(9) y
C14 P1 O1 . . . 93.09(11) y
O2 P1 O3 . . . 85.77(9) y
C14 P1 O3 . . . 86.78(11) y
O1 P1 O3 . . . 175.48(9) y
O2 P1 C1 . . . 105.66(12) y
C14 P1 C1 . . . 126.96(13) y
O1 P1 C1 . . . 92.85(11) y
O3 P1 C1 . . . 90.83(11) y
C7 O1 P1 . . . 111.77(15) y
C8 O2 P1 . . . 112.60(17) y
C13 O3 P1 . . . 114.86(17) y
C13 N1 C14 . . . 113.8(3) y
C13 N1 C15 . . . 124.5(2) y
C14 N1 C15 . . . 120.5(2) y
C6 C1 C2 . . . 117.7(3) y
C6 C1 P1 . . . 121.0(2) y
C2 C1 P1 . . . 121.2(2) y
C3 C2 C1 . . . 121.0(3) y
C3 C2 H2 . . . 119.5 ?
C1 C2 H2 . . . 119.5 ?
C4 C3 C2 . . . 120.6(3) y
C4 C3 H3 . . . 119.7 ?
C2 C3 H3 . . . 119.7 ?
C3 C4 C5 . . . 119.2(3) y
C3 C4 H4 . . . 120.4 ?
C5 C4 H4 . . . 120.4 ?
C4 C5 C6 . . . 120.4(3) y
C4 C5 H5 . . . 119.8 ?
C6 C5 H5 . . . 119.8 ?
C1 C6 C5 . . . 121.0(3) y
C1 C6 H6 . . . 119.5 ?
C5 C6 H6 . . . 119.5 ?
O1 C7 C12 . . . 127.4(3) y
O1 C7 C8 . . . 111.9(2) y
C12 C7 C8 . . . 120.8(3) y
C9 C8 O2 . . . 125.9(3) y
C9 C8 C7 . . . 121.8(3) y
O2 C8 C7 . . . 112.3(3) y
C8 C9 C10 . . . 117.2(3) y
C8 C9 H9 . . . 121.4 ?
C10 C9 H9 . . . 121.4 ?
C11 C10 C9 . . . 121.2(3) y
C11 C10 H10 . . . 119.4 ?
C9 C10 H10 . . . 119.4 ?
C10 C11 C12 . . . 121.1(3) y
C10 C11 H11 . . . 119.5 ?
C12 C11 H11 . . . 119.5 ?
C7 C12 C11 . . . 117.9(3) y
C7 C12 H12 . . . 121.1 ?
C11 C12 H12 . . . 121.1 ?
N1 C13 O3 . . . 112.5(2) y
N1 C13 C16 . . . 128.2(3) y
O3 C13 C16 . . . 119.2(3) y
N1 C14 C22 . . . 118.3(3) y
N1 C14 P1 . . . 111.9(2) y
C22 C14 P1 . . . 129.6(2) y
N1 C15 H15A . . . 109.5 ?
N1 C15 H15B . . . 109.5 ?
H15A C15 H15B . . . 109.5 ?
N1 C15 H15C . . . 109.5 ?
H15A C15 H15C . . . 109.5 ?
H15B C15 H15C . . . 109.5 ?
C17 C16 C21 . . . 118.7(3) y
C17 C16 C13 . . . 118.1(3) y
C21 C16 C13 . . . 123.1(3) y
C18 C17 C16 . . . 120.5(3) y
C18 C17 H17 . . . 119.8 ?
C16 C17 H17 . . . 119.8 ?
C19 C18 C17 . . . 120.3(3) y
C19 C18 H18 . . . 119.9 ?
C17 C18 H18 . . . 119.9 ?
C18 C19 C20 . . . 120.2(3) y
C18 C19 H19 . . . 119.9 ?
C20 C19 H19 . . . 119.9 ?
C19 C20 C21 . . . 120.0(3) y
C19 C20 H20 . . . 120 ?
C21 C20 H20 . . . 120 ?
C20 C21 C16 . . . 120.4(3) y
C20 C21 H21 . . . 119.8 ?
C16 C21 H21 . . . 119.8 ?
C23 C22 C27 . . . 117.0(3) y
C23 C22 C14 . . . 121.2(2) y
C27 C22 C14 . . . 121.8(3) y
C24 C23 C22 . . . 122.3(3) y
C24 C23 H23 . . . 118.9 ?
C22 C23 H23 . . . 118.9 ?
C23 C24 C25 . . . 119.3(3) y
C23 C24 H24 . . . 120.3 ?
C25 C24 H24 . . . 120.3 ?
C26 C25 C24 . . . 119.4(3) y
C26 C25 H25 . . . 120.3 ?
C24 C25 H25 . . . 120.3 ?
C25 C26 C27 . . . 121.1(3) y
C25 C26 H26 . . . 119.5 ?
C27 C26 H26 . . . 119.5 ?
C26 C27 C22 . . . 120.9(3) y
C26 C27 H27 . . . 119.6 ?
C22 C27 H27 . . . 119.6 ?
C32 C31 C36 . . . 120 y
C32 C31 H31 . . . 120 ?
C36 C31 H31 . . . 120 ?
C33 C32 C31 . . . 120 y
C33 C32 H32 . . . 120 ?
C31 C32 H32 . . . 120 ?
C32 C33 C34 . . . 120 y
C32 C33 H33 . . . 120 ?
C34 C33 H33 . . . 120 ?
C35 C34 C33 . . . 120 y
C35 C34 H34 . . . 120 ?
C33 C34 H34 . . . 120 ?
C34 C35 C36 . . . 120 y
C34 C35 H35 . . . 120 ?
C36 C35 H35 . . . 120 ?
C35 C36 C31 . . . 120 y
C35 C36 H36 . . . 120 ?
C31 C36 H36 . . . 120 ?
C43 C41 C42 2_656 . . 119.0(4) y
C43 C41 H41 2_656 . . 120.5 ?
C42 C41 H41 . . . 120.5 ?
C41 C42 C43 . . . 120.6(3) y
C41 C42 H42 . . . 119.7 ?
C43 C42 H42 . . . 119.7 ?
C41 C43 C42 2_656 . . 120.4(3) y
C41 C43 H43 2_656 . . 119.8 ?
C42 C43 H43 . . . 119.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O2 . . 1.6772(19) y
P1 C14 . . 1.706(3) y
P1 O1 . . 1.7281(18) y
P1 O3 . . 1.7894(18) y
P1 C1 . . 1.824(3) y
O1 C7 . . 1.369(3) y
O2 C8 . . 1.386(3) y
O3 C13 . . 1.317(3) y
N1 C13 . . 1.316(3) y
N1 C14 . . 1.434(3) y
N1 C15 . . 1.475(4) y
C1 C6 . . 1.389(4) y
C1 C2 . . 1.397(4) y
C2 C3 . . 1.381(4) y
C2 H2 . . 0.95 ?
C3 C4 . . 1.378(4) y
C3 H3 . . 0.95 ?
C4 C5 . . 1.379(4) y
C4 H4 . . 0.95 ?
C5 C6 . . 1.390(4) y
C5 H5 . . 0.95 ?
C6 H6 . . 0.95 ?
C7 C12 . . 1.374(4) y
C7 C8 . . 1.387(4) y
C8 C9 . . 1.378(4) y
C9 C10 . . 1.392(4) y
C9 H9 . . 0.95 ?
C10 C11 . . 1.375(4) y
C10 H10 . . 0.95 ?
C11 C12 . . 1.394(4) y
C11 H11 . . 0.95 ?
C12 H12 . . 0.95 ?
C13 C16 . . 1.462(4) y
C14 C22 . . 1.473(4) y
C15 H15a . . 0.98 ?
C15 H15b . . 0.98 ?
C15 H15c . . 0.98 ?
C16 C17 . . 1.386(4) y
C16 C21 . . 1.402(4) y
C17 C18 . . 1.384(4) y
C17 H17 . . 0.95 ?
C18 C19 . . 1.378(4) y
C18 H18 . . 0.95 ?
C19 C20 . . 1.378(4) y
C19 H19 . . 0.95 ?
C20 C21 . . 1.384(4) y
C20 H20 . . 0.95 ?
C21 H21 . . 0.95 ?
C22 C23 . . 1.395(4) y
C22 C27 . . 1.405(4) y
C23 C24 . . 1.388(4) y
C23 H23 . . 0.95 ?
C24 C25 . . 1.393(4) y
C24 H24 . . 0.95 ?
C25 C26 . . 1.377(4) y
C25 H25 . . 0.95 ?
C26 C27 . . 1.383(4) y
C26 H26 . . 0.95 ?
C27 H27 . . 0.95 ?
C31 C32 . . 1.39 y
C31 C36 . . 1.39 y
C31 H31 . . 0.95 ?
C32 C33 . . 1.39 y
C32 H32 . . 0.95 ?
C33 C34 . . 1.39 y
C33 H33 . . 0.95 ?
C34 C35 . . 1.39 y
C34 H34 . . 0.95 ?
C35 C36 . . 1.39 y
C35 H35 . . 0.95 ?
C36 H36 . . 0.95 ?
C41 C43 . 2_656 1.370(4) y
C41 C42 . . 1.372(4) y
C41 H41 . . 0.95 ?
C42 C43 . . 1.381(5) y
C42 H42 . . 0.95 ?
C43 C41 . 2_656 1.370(4) y
C43 H43 . . 0.95 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 P1 O1 C7 . . . . 8.46(18) y
C14 P1 O1 C7 . . . . -118.56(19) y
C1 P1 O1 C7 . . . . 114.17(19) y
C14 P1 O2 C8 . . . . 87.2(2) y
O1 P1 O2 C8 . . . . -7.21(18) y
O3 P1 O2 C8 . . . . 169.96(18) y
C1 P1 O2 C8 . . . . -100.36(19) y
O2 P1 O3 C13 . . . . -124.29(18) y
C14 P1 O3 C13 . . . . 3.09(19) y
C1 P1 O3 C13 . . . . 130.07(19) y
O2 P1 C1 C6 . . . . 53.4(2) y
C14 P1 C1 C6 . . . . -134.1(2) y
O1 P1 C1 C6 . . . . -38.1(2) y
O3 P1 C1 C6 . . . . 139.3(2) y
O2 P1 C1 C2 . . . . -125.7(2) y
C14 P1 C1 C2 . . . . 46.7(3) y
O1 P1 C1 C2 . . . . 142.8(2) y
O3 P1 C1 C2 . . . . -39.9(2) y
C6 C1 C2 C3 . . . . -1.8(4) y
P1 C1 C2 C3 . . . . 177.4(2) y
C1 C2 C3 C4 . . . . -0.7(5) y
C2 C3 C4 C5 . . . . 2.7(5) y
C3 C4 C5 C6 . . . . -2.3(5) y
C2 C1 C6 C5 . . . . 2.2(4) y
P1 C1 C6 C5 . . . . -177.0(2) y
C4 C5 C6 C1 . . . . -0.2(4) y
P1 O1 C7 C12 . . . . 172.6(3) y
P1 O1 C7 C8 . . . . -7.5(3) y
P1 O2 C8 C9 . . . . -175.0(2) y
P1 O2 C8 C7 . . . . 4.3(3) y
O1 C7 C8 C9 . . . . -178.5(3) y
C12 C7 C8 C9 . . . . 1.4(4) y
O1 C7 C8 O2 . . . . 2.2(3) y
C12 C7 C8 O2 . . . . -177.9(2) y
O2 C8 C9 C10 . . . . 178.5(3) y
C7 C8 C9 C10 . . . . -0.7(4) y
C8 C9 C10 C11 . . . . -0.2(4) y
C9 C10 C11 C12 . . . . 0.4(5) y
O1 C7 C12 C11 . . . . 178.7(3) y
C8 C7 C12 C11 . . . . -1.2(4) y
C10 C11 C12 C7 . . . . 0.3(4) y
C14 N1 C13 O3 . . . . 2.1(3) y
C15 N1 C13 O3 . . . . 169.4(2) y
C14 N1 C13 C16 . . . . -177.2(2) y
C15 N1 C13 C16 . . . . -9.9(4) y
P1 O3 C13 N1 . . . . -3.5(3) y
P1 O3 C13 C16 . . . . 175.81(18) y
C13 N1 C14 C22 . . . . -174.8(2) y
C15 N1 C14 C22 . . . . 17.3(4) y
C13 N1 C14 P1 . . . . 0.3(3) y
C15 N1 C14 P1 . . . . -167.6(2) y
O2 P1 C14 N1 . . . . 80.5(2) y
O1 P1 C14 N1 . . . . 173.67(18) y
O3 P1 C14 N1 . . . . -1.80(18) y
C1 P1 C14 N1 . . . . -90.4(2) y
O2 P1 C14 C22 . . . . -105.1(3) y
O1 P1 C14 C22 . . . . -11.9(3) y
O3 P1 C14 C22 . . . . 172.6(3) y
C1 P1 C14 C22 . . . . 84.0(3) y
N1 C13 C16 C17 . . . . 148.4(3) y
O3 C13 C16 C17 . . . . -30.8(4) y
N1 C13 C16 C21 . . . . -35.4(4) y
O3 C13 C16 C21 . . . . 145.3(3) y
C21 C16 C17 C18 . . . . 1.6(4) y
C13 C16 C17 C18 . . . . 177.9(3) y
C16 C17 C18 C19 . . . . -1.6(4) y
C17 C18 C19 C20 . . . . 0.8(5) y
C18 C19 C20 C21 . . . . -0.2(5) y
C19 C20 C21 C16 . . . . 0.2(5) y
C17 C16 C21 C20 . . . . -0.9(4) y
C13 C16 C21 C20 . . . . -177.0(3) y
N1 C14 C22 C23 . . . . 58.2(4) y
P1 C14 C22 C23 . . . . -115.9(3) y
N1 C14 C22 C27 . . . . -120.4(3) y
P1 C14 C22 C27 . . . . 65.5(4) y
C27 C22 C23 C24 . . . . 1.0(4) y
C14 C22 C23 C24 . . . . -177.7(3) y
C22 C23 C24 C25 . . . . -1.5(4) y
C23 C24 C25 C26 . . . . 0.3(4) y
C24 C25 C26 C27 . . . . 1.3(4) y
C25 C26 C27 C22 . . . . -1.8(4) y
C23 C22 C27 C26 . . . . 0.6(4) y
C14 C22 C27 C26 . . . . 179.3(3) y
C36 C31 C32 C33 . . . . 0 y
C31 C32 C33 C34 . . . . 0 y
C32 C33 C34 C35 . . . . 0 y
C33 C34 C35 C36 . . . . 0 y
C34 C35 C36 C31 . . . . 0 y
C32 C31 C36 C35 . . . . 0 y
C43 C41 C42 C43 2_656 . . . -1.1(4) y
C41 C42 C43 C41 . . . 2_656 1.1(5) y
