#------------------------------------------------------------------------------
#$Date: 2016-03-23 00:05:14 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179092 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/54/4305455.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_4305455
loop_
_publ_author_name
'Anna Młodzianowska'
'Lechosław Latos-Grażyński'
'Ludmiła Szterenberg'
_publ_section_title
;
Phosphorus Complexes of N-Fused Porphyrin and Its Reduced Derivatives: New
Isomers of Porphyrin Stabilized via Coordination
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              6364
_journal_page_last               6374
_journal_paper_doi               10.1021/ic800437y
_journal_volume                  47
_journal_year                    2008
_chemical_formula_moiety         'C44 H27 N4 O P, C Cl2'
_chemical_formula_sum            'C45 H27 Cl2 N4 O P'
_chemical_formula_weight         741.58
_chemical_name_systematic
; 
 ? 
;
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.91(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.968(5)
_cell_length_b                   10.148(3)
_cell_length_c                   22.786(7)
_cell_measurement_reflns_used    23521
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      38.4
_cell_measurement_theta_min      4.0
_cell_volume                     3533(2)
_computing_cell_refinement       'CrysalisRED (Oxford Diffraction,2006)'
_computing_data_collection       'CrysalisRED (Oxford Diffraction,2006)'
_computing_data_reduction        'CrysalisRED (Oxford Diffraction,2006)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'Xcalibur PX kappa-geometry diffractometer with CCD Onyx camera'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0830
_diffrn_reflns_av_sigmaI/netI    0.0884
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            54082
_diffrn_reflns_theta_full        27.0
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         4.12
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1528
_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_min          0.083
_refine_diff_density_max         0.827
_refine_diff_density_min         -0.872
_refine_diff_density_rms         0.063
_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     497
_refine_ls_number_reflns         7663
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0519
_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)+(0.0600P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1288
_reflns_number_gt                4283
_reflns_number_total             7663
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic800437y-file001.cif
_cod_data_source_block           aml1
_cod_original_cell_volume        3532.7(19)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4305455
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P P 0.18843(4) 0.13330(7) 0.45766(3) 0.02137(17) Uani 1 1 d . . .
O O 0.20544(11) 0.27123(17) 0.44790(7) 0.0258(4) Uani 1 1 d . . .
N21 N -0.02233(13) 0.1728(2) 0.37947(9) 0.0209(5) Uani 1 1 d . . .
N22 N 0.12373(12) 0.0601(2) 0.39557(9) 0.0202(5) Uani 1 1 d . . .
N23 N 0.26704(13) 0.0228(2) 0.47095(9) 0.0224(5) Uani 1 1 d . . .
N24 N 0.14937(12) 0.1057(2) 0.51711(9) 0.0206(5) Uani 1 1 d . . .
C1 C -0.04411(15) 0.2312(2) 0.42891(11) 0.0208(6) Uani 1 1 d . . .
C2 C -0.12744(16) 0.2977(2) 0.39907(11) 0.0225(6) Uani 1 1 d . . .
H2 H -0.1585 0.3514 0.4198 0.027 Uiso 1 1 calc R . .
C3 C -0.15384(16) 0.2728(2) 0.33882(12) 0.0237(6) Uani 1 1 d . . .
H3 H -0.2067 0.3034 0.3108 0.028 Uiso 1 1 calc R . .
C4 C -0.08937(16) 0.1921(2) 0.32333(11) 0.0227(6) Uani 1 1 d . . .
C5 C -0.06765(16) 0.1314(2) 0.27547(11) 0.0216(6) Uani 1 1 d . . .
C6 C 0.01888(16) 0.0741(2) 0.30298(11) 0.0217(6) Uani 1 1 d . . .
C7 C 0.09373(16) 0.0132(2) 0.29291(11) 0.0224(6) Uani 1 1 d . . .
H7 H 0.0984 -0.0178 0.2546 0.027 Uiso 1 1 calc R . .
C8 C 0.15870(16) 0.0069(2) 0.34842(11) 0.0226(6) Uani 1 1 d . . .
C9 C 0.04077(16) 0.1011(2) 0.36502(11) 0.0209(6) Uani 1 1 d . . .
C10 C 0.24783(16) -0.0352(2) 0.36413(12) 0.0233(6) Uani 1 1 d . . .
C11 C 0.30021(16) -0.0288(2) 0.42408(12) 0.0245(6) Uani 1 1 d . . .
C12 C 0.38240(16) -0.0871(3) 0.45618(12) 0.0270(6) Uani 1 1 d . . .
H12 H 0.4228 -0.1242 0.4374 0.032 Uiso 1 1 calc R . .
C13 C 0.39372(17) -0.0811(3) 0.51721(13) 0.0287(6) Uani 1 1 d . . .
H13 H 0.4432 -0.1140 0.5479 0.034 Uiso 1 1 calc R . .
C14 C 0.31976(16) -0.0177(3) 0.52885(11) 0.0235(6) Uani 1 1 d . . .
C15 C 0.28945(16) -0.0061(2) 0.57888(11) 0.0230(6) Uani 1 1 d . . .
C16 C 0.20492(16) 0.0504(2) 0.57325(11) 0.0214(6) Uani 1 1 d . . .
C17 C 0.16117(16) 0.0635(2) 0.61649(12) 0.0238(6) Uani 1 1 d . . .
H17 H 0.1816 0.0335 0.6577 0.029 Uiso 1 1 calc R . .
C18 C 0.08221(16) 0.1276(2) 0.59060(11) 0.0230(6) Uani 1 1 d . . .
H18 H 0.0405 0.1484 0.6116 0.028 Uiso 1 1 calc R . .
C19 C 0.07320(16) 0.1569(2) 0.52928(11) 0.0196(6) Uani 1 1 d . . .
C20 C -0.00317(15) 0.2249(2) 0.49054(11) 0.0206(6) Uani 1 1 d . . .
C21 C -0.12038(17) 0.1241(2) 0.21131(11) 0.0248(6) Uani 1 1 d . . .
C22 C -0.21119(18) 0.1198(3) 0.19578(12) 0.0307(7) Uani 1 1 d . . .
H22 H -0.2393 0.1224 0.2272 0.037 Uiso 1 1 calc R . .
C23 C -0.2612(2) 0.1116(3) 0.13503(14) 0.0412(8) Uani 1 1 d . . .
H23 H -0.3233 0.1098 0.1252 0.049 Uiso 1 1 calc R . .
C24 C -0.2215(2) 0.1061(3) 0.08867(14) 0.0468(9) Uani 1 1 d . . .
H24 H -0.2559 0.0987 0.0471 0.056 Uiso 1 1 calc R . .
C25 C -0.1316(3) 0.1115(3) 0.10324(14) 0.0518(9) Uani 1 1 d . . .
H25 H -0.1041 0.1096 0.0715 0.062 Uiso 1 1 calc R . .
C26 C -0.0806(2) 0.1197(3) 0.16437(12) 0.0372(7) Uani 1 1 d . . .
H26 H -0.0186 0.1223 0.1740 0.045 Uiso 1 1 calc R . .
C27 C 0.28336(17) -0.0862(3) 0.31520(12) 0.0255(6) Uani 1 1 d . . .
C28 C 0.23897(18) -0.1826(3) 0.27439(12) 0.0307(7) Uani 1 1 d . . .
H28 H 0.1870 -0.2204 0.2793 0.037 Uiso 1 1 calc R . .
C29 C 0.2703(2) -0.2238(3) 0.22665(13) 0.0374(7) Uani 1 1 d . . .
H29 H 0.2393 -0.2892 0.1989 0.045 Uiso 1 1 calc R . .
C30 C 0.3458(2) -0.1710(3) 0.21914(14) 0.0397(8) Uani 1 1 d . . .
H30 H 0.3663 -0.1983 0.1859 0.048 Uiso 1 1 calc R . .
C31 C 0.39134(19) -0.0784(3) 0.26003(14) 0.0381(7) Uani 1 1 d . . .
H31 H 0.4444 -0.0433 0.2557 0.046 Uiso 1 1 calc R . .
C32 C 0.36016(17) -0.0356(3) 0.30793(13) 0.0315(7) Uani 1 1 d . . .
H32 H 0.3919 0.0289 0.3358 0.038 Uiso 1 1 calc R . .
C33 C 0.33909(15) -0.0638(3) 0.63918(11) 0.0237(6) Uani 1 1 d . . .
C34 C 0.36514(17) -0.1951(3) 0.64321(12) 0.0278(6) Uani 1 1 d . . .
H34 H 0.3523 -0.2474 0.6071 0.033 Uiso 1 1 calc R . .
C35 C 0.40951(18) -0.2510(3) 0.69908(13) 0.0357(7) Uani 1 1 d . . .
H35 H 0.4277 -0.3404 0.7009 0.043 Uiso 1 1 calc R . .
C36 C 0.42737(18) -0.1771(3) 0.75224(13) 0.0349(7) Uani 1 1 d . . .
H36 H 0.4572 -0.2158 0.7906 0.042 Uiso 1 1 calc R . .
C37 C 0.40163(17) -0.0468(3) 0.74937(12) 0.0322(7) Uani 1 1 d . . .
H37 H 0.4137 0.0042 0.7859 0.039 Uiso 1 1 calc R . .
C38 C 0.35800(16) 0.0102(3) 0.69321(12) 0.0285(6) Uani 1 1 d . . .
H38 H 0.3409 0.1001 0.6916 0.034 Uiso 1 1 calc R . .
C39 C -0.05168(16) 0.2965(2) 0.52898(11) 0.0213(6) Uani 1 1 d . . .
C40 C -0.01744(16) 0.4115(2) 0.56043(11) 0.0218(6) Uani 1 1 d . . .
H40 H 0.0365 0.4458 0.5573 0.026 Uiso 1 1 calc R . .
C41 C -0.06120(16) 0.4755(3) 0.59588(11) 0.0243(6) Uani 1 1 d . . .
H41 H -0.0373 0.5539 0.6170 0.029 Uiso 1 1 calc R . .
C42 C -0.14011(17) 0.4265(3) 0.60113(12) 0.0281(6) Uani 1 1 d . . .
H42 H -0.1698 0.4706 0.6260 0.034 Uiso 1 1 calc R . .
C43 C -0.17485(17) 0.3132(3) 0.56986(12) 0.0296(7) Uani 1 1 d . . .
H43 H -0.2288 0.2794 0.5731 0.036 Uiso 1 1 calc R . .
C44 C -0.13114(17) 0.2485(3) 0.53359(12) 0.0257(6) Uani 1 1 d . . .
H44 H -0.1557 0.1712 0.5119 0.031 Uiso 1 1 calc R . .
Cl1 Cl 0.35471(7) 0.56998(9) 0.36767(5) 0.0697(3) Uani 1 1 d . A 1
C1R C 0.3653(5) 0.4585(7) 0.4337(3) 0.056(2) Uiso 0.60 1 d P A 1
Cl2 Cl 0.43892(14) 0.3289(2) 0.39300(15) 0.0649(7) Uani 0.40 1 d P A 1
Cl3 Cl 0.4123(3) 0.5349(6) 0.4714(3) 0.0790(15) Uani 0.20 1 d P B 2
C2R C 0.3606(5) 0.4379(8) 0.4100(4) 0.034(2) Uiso 0.40 1 d P C 3
Cl4 Cl 0.45218(15) 0.3465(2) 0.44613(12) 0.0578(6) Uani 0.40 1 d P C 3
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'
Cl Cl 0.1484 0.1585 '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
O P N23 121.18(11) . . ?
O P N22 113.37(10) . . ?
N23 P N22 95.96(11) . . ?
O P N24 114.54(10) . . ?
N23 P N24 100.44(10) . . ?
N22 P N24 109.18(10) . . ?
C9 N21 C1 142.7(2) . . ?
C9 N21 C4 105.8(2) . . ?
C1 N21 C4 111.5(2) . . ?
C9 N22 C8 105.08(19) . . ?
C9 N22 P 124.46(17) . . ?
C8 N22 P 121.19(16) . . ?
C14 N23 C11 110.2(2) . . ?
C14 N23 P 126.12(17) . . ?
C11 N23 P 122.94(17) . . ?
C19 N24 C16 108.05(19) . . ?
C19 N24 P 129.68(17) . . ?
C16 N24 P 120.40(16) . . ?
C20 C1 N21 130.4(2) . . ?
C20 C1 C2 126.5(2) . . ?
N21 C1 C2 103.0(2) . . ?
C3 C2 C1 111.1(2) . . ?
C3 C2 H2 124.4 . . ?
C1 C2 H2 124.4 . . ?
C2 C3 C4 109.0(2) . . ?
C2 C3 H3 125.5 . . ?
C4 C3 H3 125.5 . . ?
C5 C4 N21 110.6(2) . . ?
C5 C4 C3 144.1(2) . . ?
N21 C4 C3 105.2(2) . . ?
C4 C5 C21 127.5(2) . . ?
C4 C5 C6 105.2(2) . . ?
C21 C5 C6 127.3(2) . . ?
C9 C6 C7 106.1(2) . . ?
C9 C6 C5 106.6(2) . . ?
C7 C6 C5 146.9(2) . . ?
C8 C7 C6 108.3(2) . . ?
C8 C7 H7 125.8 . . ?
C6 C7 H7 125.8 . . ?
C7 C8 C10 132.1(2) . . ?
C7 C8 N22 108.2(2) . . ?
C10 C8 N22 119.7(2) . . ?
N21 C9 N22 135.7(2) . . ?
N21 C9 C6 111.7(2) . . ?
N22 C9 C6 112.3(2) . . ?
C11 C10 C8 120.4(2) . . ?
C11 C10 C27 120.4(2) . . ?
C8 C10 C27 119.2(2) . . ?
C10 C11 N23 120.6(2) . . ?
C10 C11 C12 133.5(2) . . ?
N23 C11 C12 104.8(2) . . ?
C13 C12 C11 109.6(2) . . ?
C13 C12 H12 125.2 . . ?
C11 C12 H12 125.2 . . ?
C12 C13 C14 109.8(2) . . ?
C12 C13 H13 125.1 . . ?
C14 C13 H13 125.1 . . ?
C15 C14 N23 119.8(2) . . ?
C15 C14 C13 134.6(2) . . ?
N23 C14 C13 105.0(2) . . ?
C14 C15 C16 120.7(2) . . ?
C14 C15 C33 120.8(2) . . ?
C16 C15 C33 118.2(2) . . ?
C17 C16 C15 129.5(2) . . ?
C17 C16 N24 106.8(2) . . ?
C15 C16 N24 123.6(2) . . ?
C16 C17 C18 109.3(2) . . ?
C16 C17 H17 125.4 . . ?
C18 C17 H17 125.4 . . ?
C17 C18 C19 110.0(2) . . ?
C17 C18 H18 125.0 . . ?
C19 C18 H18 125.0 . . ?
C18 C19 N24 105.8(2) . . ?
C18 C19 C20 122.2(2) . . ?
N24 C19 C20 132.0(2) . . ?
C1 C20 C19 135.3(2) . . ?
C1 C20 C39 113.6(2) . . ?
C19 C20 C39 110.9(2) . . ?
C22 C21 C26 118.5(2) . . ?
C22 C21 C5 120.7(2) . . ?
C26 C21 C5 120.7(2) . . ?
C23 C22 C21 120.8(3) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C24 C23 C22 120.4(3) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 C23 119.5(3) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 120.5(3) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 120.2(3) . . ?
C21 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C32 C27 C28 118.5(2) . . ?
C32 C27 C10 120.4(2) . . ?
C28 C27 C10 121.0(2) . . ?
C29 C28 C27 120.4(3) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C30 C29 C28 120.6(3) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C31 C30 C29 119.5(3) . . ?
C31 C30 H30 120.2 . . ?
C29 C30 H30 120.2 . . ?
C30 C31 C32 120.3(3) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C27 C32 C31 120.6(3) . . ?
C27 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C34 C33 C38 118.2(2) . . ?
C34 C33 C15 120.4(2) . . ?
C38 C33 C15 121.4(2) . . ?
C35 C34 C33 121.0(3) . . ?
C35 C34 H34 119.5 . . ?
C33 C34 H34 119.5 . . ?
C36 C35 C34 120.3(3) . . ?
C36 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C37 C36 C35 119.7(3) . . ?
C37 C36 H36 120.2 . . ?
C35 C36 H36 120.2 . . ?
C36 C37 C38 120.3(3) . . ?
C36 C37 H37 119.9 . . ?
C38 C37 H37 119.9 . . ?
C37 C38 C33 120.6(3) . . ?
C37 C38 H38 119.7 . . ?
C33 C38 H38 119.7 . . ?
C44 C39 C40 118.9(2) . . ?
C44 C39 C20 120.5(2) . . ?
C40 C39 C20 120.6(2) . . ?
C41 C40 C39 120.4(2) . . ?
C41 C40 H40 119.8 . . ?
C39 C40 H40 119.8 . . ?
C40 C41 C42 120.6(2) . . ?
C40 C41 H41 119.7 . . ?
C42 C41 H41 119.7 . . ?
C43 C42 C41 119.4(2) . . ?
C43 C42 H42 120.3 . . ?
C41 C42 H42 120.3 . . ?
C42 C43 C44 120.2(2) . . ?
C42 C43 H43 119.9 . . ?
C44 C43 H43 119.9 . . ?
C39 C44 C43 120.4(2) . . ?
C39 C44 H44 119.8 . . ?
C43 C44 H44 119.8 . . ?
Cl1 C1R Cl2 87.4(3) . . ?
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
P O 1.4553(18) . ?
P N23 1.645(2) . ?
P N22 1.664(2) . ?
P N24 1.672(2) . ?
N21 C9 1.359(3) . ?
N21 C1 1.403(3) . ?
N21 C4 1.423(3) . ?
N22 C9 1.370(3) . ?
N22 C8 1.451(3) . ?
N23 C14 1.404(3) . ?
N23 C11 1.423(3) . ?
N24 C19 1.422(3) . ?
N24 C16 1.441(3) . ?
C1 C20 1.367(3) . ?
C1 C2 1.470(3) . ?
C2 C3 1.338(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.437(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(3) . ?
C5 C21 1.462(3) . ?
C5 C6 1.462(3) . ?
C6 C9 1.381(3) . ?
C6 C7 1.422(3) . ?
C7 C8 1.385(3) . ?
C7 H7 0.9500 . ?
C8 C10 1.428(3) . ?
C10 C11 1.380(4) . ?
C10 C27 1.484(3) . ?
C11 C12 1.431(3) . ?
C12 C13 1.350(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.436(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.367(3) . ?
C15 C16 1.437(3) . ?
C15 C33 1.492(3) . ?
C16 C17 1.370(3) . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.395(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.455(3) . ?
C20 C39 1.513(3) . ?
C21 C22 1.390(4) . ?
C21 C26 1.394(4) . ?
C22 C23 1.385(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.377(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.397(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C32 1.383(4) . ?
C27 C28 1.393(4) . ?
C28 C29 1.387(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.375(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.373(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.394(4) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C34 1.391(4) . ?
C33 C38 1.398(4) . ?
C34 C35 1.385(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.382(4) . ?
C35 H35 0.9500 . ?
C36 C37 1.381(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.392(4) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 C44 1.391(3) . ?
C39 C40 1.395(3) . ?
C40 C41 1.375(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.392(4) . ?
C41 H41 0.9500 . ?
C42 C43 1.381(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.392(4) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?
Cl1 C1R 1.850(7) . ?
C1R Cl2 2.147(8) . ?
C2R Cl4 1.725(8) . ?
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
O P N22 C9 -58.2(2) . . . . ?
N23 P N22 C9 174.0(2) . . . . ?
N24 P N22 C9 70.8(2) . . . . ?
O P N22 C8 83.4(2) . . . . ?
N23 P N22 C8 -44.3(2) . . . . ?
N24 P N22 C8 -147.59(18) . . . . ?
O P N23 C14 92.7(2) . . . . ?
N22 P N23 C14 -145.4(2) . . . . ?
N24 P N23 C14 -34.6(2) . . . . ?
O P N23 C11 -76.4(2) . . . . ?
N22 P N23 C11 45.6(2) . . . . ?
N24 P N23 C11 156.37(19) . . . . ?
O P N24 C19 57.2(2) . . . . ?
N23 P N24 C19 -171.2(2) . . . . ?
N22 P N24 C19 -71.1(2) . . . . ?
O P N24 C16 -105.22(19) . . . . ?
N23 P N24 C16 26.3(2) . . . . ?
N22 P N24 C16 126.44(18) . . . . ?
C9 N21 C1 C20 -6.4(5) . . . . ?
C4 N21 C1 C20 172.6(3) . . . . ?
C9 N21 C1 C2 176.9(3) . . . . ?
C4 N21 C1 C2 -4.1(3) . . . . ?
C20 C1 C2 C3 -173.1(2) . . . . ?
N21 C1 C2 C3 3.7(3) . . . . ?
C1 C2 C3 C4 -2.0(3) . . . . ?
C9 N21 C4 C5 0.7(3) . . . . ?
C1 N21 C4 C5 -178.7(2) . . . . ?
C9 N21 C4 C3 -177.6(2) . . . . ?
C1 N21 C4 C3 3.1(3) . . . . ?
C2 C3 C4 C5 -177.8(3) . . . . ?
C2 C3 C4 N21 -0.6(3) . . . . ?
N21 C4 C5 C21 177.5(2) . . . . ?
C3 C4 C5 C21 -5.4(5) . . . . ?
N21 C4 C5 C6 -1.6(3) . . . . ?
C3 C4 C5 C6 175.6(3) . . . . ?
C4 C5 C6 C9 1.8(3) . . . . ?
C21 C5 C6 C9 -177.2(2) . . . . ?
C4 C5 C6 C7 -168.9(4) . . . . ?
C21 C5 C6 C7 12.0(6) . . . . ?
C9 C6 C7 C8 -0.9(3) . . . . ?
C5 C6 C7 C8 169.9(4) . . . . ?
C6 C7 C8 C10 -175.0(3) . . . . ?
C6 C7 C8 N22 2.3(3) . . . . ?
C9 N22 C8 C7 -2.8(3) . . . . ?
P N22 C8 C7 -150.78(18) . . . . ?
C9 N22 C8 C10 174.9(2) . . . . ?
P N22 C8 C10 26.9(3) . . . . ?
C1 N21 C9 N22 -8.1(5) . . . . ?
C4 N21 C9 N22 172.9(3) . . . . ?
C1 N21 C9 C6 179.6(3) . . . . ?
C4 N21 C9 C6 0.6(3) . . . . ?
C8 N22 C9 N21 -170.0(3) . . . . ?
P N22 C9 N21 -23.4(4) . . . . ?
C8 N22 C9 C6 2.3(3) . . . . ?
P N22 C9 C6 148.95(19) . . . . ?
C7 C6 C9 N21 173.3(2) . . . . ?
C5 C6 C9 N21 -1.5(3) . . . . ?
C7 C6 C9 N22 -1.0(3) . . . . ?
C5 C6 C9 N22 -175.7(2) . . . . ?
C7 C8 C10 C11 178.6(3) . . . . ?
N22 C8 C10 C11 1.7(4) . . . . ?
C7 C8 C10 C27 -1.5(4) . . . . ?
N22 C8 C10 C27 -178.5(2) . . . . ?
C8 C10 C11 N23 -1.6(4) . . . . ?
C27 C10 C11 N23 178.6(2) . . . . ?
C8 C10 C11 C12 164.2(3) . . . . ?
C27 C10 C11 C12 -15.7(4) . . . . ?
C14 N23 C11 C10 161.4(2) . . . . ?
P N23 C11 C10 -28.0(3) . . . . ?
C14 N23 C11 C12 -8.0(3) . . . . ?
P N23 C11 C12 162.65(17) . . . . ?
C10 C11 C12 C13 -162.3(3) . . . . ?
N23 C11 C12 C13 5.0(3) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C11 N23 C14 C15 -164.7(2) . . . . ?
P N23 C14 C15 25.0(3) . . . . ?
C11 N23 C14 C13 7.7(3) . . . . ?
P N23 C14 C13 -162.51(18) . . . . ?
C12 C13 C14 C15 166.3(3) . . . . ?
C12 C13 C14 N23 -4.5(3) . . . . ?
N23 C14 C15 C16 -1.6(4) . . . . ?
C13 C14 C15 C16 -171.3(3) . . . . ?
N23 C14 C15 C33 172.1(2) . . . . ?
C13 C14 C15 C33 2.4(4) . . . . ?
C14 C15 C16 C17 175.8(3) . . . . ?
C33 C15 C16 C17 1.9(4) . . . . ?
C14 C15 C16 N24 -4.2(4) . . . . ?
C33 C15 C16 N24 -178.1(2) . . . . ?
C19 N24 C16 C17 2.5(3) . . . . ?
P N24 C16 C17 168.34(17) . . . . ?
C19 N24 C16 C15 -177.6(2) . . . . ?
P N24 C16 C15 -11.7(3) . . . . ?
C15 C16 C17 C18 178.4(2) . . . . ?
N24 C16 C17 C18 -1.7(3) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C17 C18 C19 N24 1.3(3) . . . . ?
C17 C18 C19 C20 -179.6(2) . . . . ?
C16 N24 C19 C18 -2.3(3) . . . . ?
P N24 C19 C18 -166.41(18) . . . . ?
C16 N24 C19 C20 178.8(2) . . . . ?
P N24 C19 C20 14.7(4) . . . . ?
N21 C1 C20 C19 -2.4(5) . . . . ?
C2 C1 C20 C19 173.6(3) . . . . ?
N21 C1 C20 C39 -176.4(2) . . . . ?
C2 C1 C20 C39 -0.5(4) . . . . ?
C18 C19 C20 C1 -155.0(3) . . . . ?
N24 C19 C20 C1 23.8(5) . . . . ?
C18 C19 C20 C39 19.2(3) . . . . ?
N24 C19 C20 C39 -162.0(2) . . . . ?
C4 C5 C21 C22 -31.9(4) . . . . ?
C6 C5 C21 C22 146.9(3) . . . . ?
C4 C5 C21 C26 148.9(3) . . . . ?
C6 C5 C21 C26 -32.3(4) . . . . ?
C26 C21 C22 C23 -0.2(4) . . . . ?
C5 C21 C22 C23 -179.4(2) . . . . ?
C21 C22 C23 C24 0.7(4) . . . . ?
C22 C23 C24 C25 -1.3(4) . . . . ?
C23 C24 C25 C26 1.3(5) . . . . ?
C22 C21 C26 C25 0.2(4) . . . . ?
C5 C21 C26 C25 179.4(3) . . . . ?
C24 C25 C26 C21 -0.8(5) . . . . ?
C11 C10 C27 C32 -52.0(3) . . . . ?
C8 C10 C27 C32 128.2(3) . . . . ?
C11 C10 C27 C28 130.2(3) . . . . ?
C8 C10 C27 C28 -49.7(3) . . . . ?
C32 C27 C28 C29 -1.7(4) . . . . ?
C10 C27 C28 C29 176.2(2) . . . . ?
C27 C28 C29 C30 0.5(4) . . . . ?
C28 C29 C30 C31 1.2(4) . . . . ?
C29 C30 C31 C32 -1.7(4) . . . . ?
C28 C27 C32 C31 1.3(4) . . . . ?
C10 C27 C32 C31 -176.6(2) . . . . ?
C30 C31 C32 C27 0.4(4) . . . . ?
C14 C15 C33 C34 -51.8(3) . . . . ?
C16 C15 C33 C34 122.1(3) . . . . ?
C14 C15 C33 C38 130.5(3) . . . . ?
C16 C15 C33 C38 -55.6(3) . . . . ?
C38 C33 C34 C35 -0.7(4) . . . . ?
C15 C33 C34 C35 -178.5(2) . . . . ?
C33 C34 C35 C36 1.1(4) . . . . ?
C34 C35 C36 C37 -0.7(4) . . . . ?
C35 C36 C37 C38 -0.1(4) . . . . ?
C36 C37 C38 C33 0.5(4) . . . . ?
C34 C33 C38 C37 -0.1(4) . . . . ?
C15 C33 C38 C37 177.7(2) . . . . ?
C1 C20 C39 C44 69.0(3) . . . . ?
C19 C20 C39 C44 -106.6(3) . . . . ?
C1 C20 C39 C40 -111.1(3) . . . . ?
C19 C20 C39 C40 73.4(3) . . . . ?
C44 C39 C40 C41 0.6(4) . . . . ?
C20 C39 C40 C41 -179.3(2) . . . . ?
C39 C40 C41 C42 0.2(4) . . . . ?
C40 C41 C42 C43 -0.6(4) . . . . ?
C41 C42 C43 C44 0.2(4) . . . . ?
C40 C39 C44 C43 -1.1(4) . . . . ?
C20 C39 C44 C43 178.8(2) . . . . ?
C42 C43 C44 C39 0.7(4) . . . . ?
