##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2005-09-20
_journal_date_accepted     2005-10-11
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue     11
_journal_page_first     o3679
_journal_page_last     o3681
_journal_paper_category     EO
_journal_coeditor_code     CI6662
_publ_contact_author_name     'Prof. De-Qing Shi'
_publ_contact_author_address
;
Key Laboratory of Pesticide and Chemical Biology
College of Chemistry
Central China Normal University
Wuhan  430079
HuBei
People's Republic of China
;
_publ_contact_author_email     chshidq@yahoo.com.cn
_publ_contact_author_fax     ?
_publ_contact_author_phone     '86-27-67867958(office)'
_publ_section_title
;\
cis-Ethyl
5-amino-1-[4-chlorophenyl-3-(6-chloro-3-pyridylmethylamino)-5,5-dimethyl-2-\
oxo-1,3,2-dioxaphosphinan-1-yl]pyrazole-4-carboxylate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Zai-Gang Luo' .
;
Key Laboratory of Pesticide and Chemical Biology of Ministry of Education
College of Chemistry
Central China Normal University
Wuhan 430079
Hubei
People's Republic of China
;
    'De-Qing Shi' .
;
Key Laboratory of Pesticide and Chemical Biology of Ministry of Education
College of Chemistry
Central China Normal University
Wuhan 430079
Hubei
People's Republic of China
;
    'Xiang-Gao Meng ' .
;
College of Chemistry
Central China Normal University
Wuhan 430079
Hubei
People's Republic of China
;
data_I
_chemical_name_systematic
;
cis-Ethyl
5-amino-1-[4-chlorophenyl-3-(6-chloro-3-pyridylmethylamino)-5,5-dimethyl-2-oxo-
1,3,2-dioxaphosphinan-1-yl]pyrazole-4-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C23 H26 Cl2 N5 O5 P'
_chemical_formula_sum     'C23 H26 Cl2 N5 O5 P'
_chemical_formula_iupac     'C23 H26 Cl2 N5 O5 P'
_chemical_formula_weight     554.36
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
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'
_cell_length_a     12.4196(11)
_cell_length_b     12.1995(11)
_cell_length_c     17.5992(15)
_cell_angle_alpha     90.00
_cell_angle_beta     107.198(2)
_cell_angle_gamma     90.00
_cell_volume     2547.3(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5782
_cell_measurement_theta_min     2.39
_cell_measurement_theta_max     22.87
_cell_measurement_temperature     292(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.446
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1152
_exptl_absorpt_coefficient_mu     0.362
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2000)'
_exptl_absorpt_correction_T_min     0.8991
_exptl_absorpt_correction_T_max     0.9377
_exptl_special_details
;
;
_diffrn_ambient_temperature     292(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     21527
_diffrn_reflns_av_R_equivalents     0.0311
_diffrn_reflns_av_sigmaI/netI     0.0332
_diffrn_reflns_theta_min     1.78
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     22
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     0
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     5812
_reflns_number_gt     3999
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0713
_refine_ls_R_factor_gt     0.0461
_refine_ls_wR_factor_gt     0.1130
_refine_ls_wR_factor_ref     0.1268
_refine_ls_goodness_of_fit_ref     1.022
_refine_ls_restrained_S_all     1.022
_refine_ls_number_reflns     5812
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.0617P)²+0.368P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.303
_refine_diff_density_min     -0.267
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'Cl' 'Cl' 0.1484 0.1585
                         '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'
_computing_data_collection     'SMART (Bruker, 2000)'
_computing_cell_refinement     'SAINT (Bruker, 2000)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1997)'
_computing_publication_material     'SHELXTL'
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    C1 1.06761(18) 0.7043(2) 0.36768(13) 0.0610(6) Uani d . 1 . . C
    C2 1.0501(2) 0.5940(2) 0.36607(15) 0.0700(7) Uani d . 1 . . C
    H2 1.0952 0.5461 0.3477 0.084 Uiso calc R 1 . . H
    C3 0.9637(2) 0.5561(2) 0.39242(15) 0.0640(6) Uani d . 1 . . C
    H3 0.9494 0.4813 0.3921 0.077 Uiso calc R 1 . . H
    C4 0.89754(17) 0.62823(17) 0.41939(12) 0.0488(5) Uani d . 1 . . C
    C5 0.92332(19) 0.73703(18) 0.41740(14) 0.0572(6) Uani d . 1 . . C
    H5 0.8794 0.7871 0.4349 0.069 Uiso calc R 1 . . H
    C6 0.80286(19) 0.58806(19) 0.44928(14) 0.0592(6) Uani d . 1 . . C
    H6A 0.7606 0.5333 0.4125 0.071 Uiso calc R 1 . . H
    H6B 0.8353 0.5521 0.5001 0.071 Uiso calc R 1 . . H
    C7 0.64604(17) 0.71098(18) 0.39535(12) 0.0486(5) Uani d . 1 . . C
    C8 0.55524(16) 0.78234(17) 0.39665(12) 0.0468(5) Uani d . 1 . . C
    C9 0.49503(16) 0.79750(17) 0.31806(12) 0.0448(5) Uani d . 1 . . C
    C10 0.52539(18) 0.83047(18) 0.46267(12) 0.0505(5) Uani d . 1 . . C
    C11 0.5914(2) 0.8615(2) 0.60365(14) 0.0681(7) Uani d . 1 . . C
    H11A 0.5578 0.8096 0.6317 0.082 Uiso calc R 1 . . H
    H11B 0.5428 0.9253 0.5902 0.082 Uiso calc R 1 . . H
    C12 0.7045(2) 0.8938(3) 0.65389(16) 0.0940(10) Uani d . 1 . . C
    H12A 0.7533 0.8311 0.6635 0.141 Uiso calc R 1 . . H
    H12B 0.6993 0.9218 0.7036 0.141 Uiso calc R 1 . . H
    H12C 0.7344 0.9494 0.6273 0.141 Uiso calc R 1 . . H
    C13 0.57560(19) 0.56549(18) 0.10016(13) 0.0541(5) Uani d . 1 . . C
    H13A 0.5292 0.5843 0.0470 0.065 Uiso calc R 1 . . H
    H13B 0.5781 0.4862 0.1042 0.065 Uiso calc R 1 . . H
    C14 0.69496(17) 0.60818(16) 0.11151(12) 0.0473(5) Uani d . 1 . . C
    C15 0.7319(2) 0.56104(19) 0.04167(14) 0.0629(6) Uani d . 1 . . C
    H15A 0.8064 0.5867 0.0453 0.094 Uiso calc R 1 . . H
    H15B 0.6803 0.5847 -0.0078 0.094 Uiso calc R 1 . . H
    H15C 0.7321 0.4824 0.0441 0.094 Uiso calc R 1 . . H
    C16 0.7752(2) 0.57043(19) 0.19067(13) 0.0618(6) Uani d . 1 . . C
    H16A 0.7512 0.6001 0.2335 0.093 Uiso calc R 1 . . H
    H16B 0.8500 0.5955 0.1951 0.093 Uiso calc R 1 . . H
    H16C 0.7748 0.4918 0.1932 0.093 Uiso calc R 1 . . H
    C17 0.68698(16) 0.73341(15) 0.10412(11) 0.0429(4) Uani d . 1 . . C
    H17 0.6377 0.7509 0.0508 0.052 Uiso calc R 1 . . H
    C18 0.79555(15) 0.79676(16) 0.11654(11) 0.0418(4) Uani d . 1 . . C
    C19 0.83358(16) 0.82185(17) 0.05196(12) 0.0473(5) Uani d . 1 . . C
    H19 0.7932 0.7973 0.0016 0.057 Uiso calc R 1 . . H
    C20 0.93045(17) 0.88279(18) 0.06135(13) 0.0545(5) Uani d . 1 . . C
    H20 0.9563 0.8981 0.0180 0.065 Uiso calc R 1 . . H
    C21 0.98784(18) 0.92036(18) 0.13579(14) 0.0558(5) Uani d . 1 . . C
    C22 0.95201(18) 0.89758(19) 0.20090(13) 0.0576(6) Uani d . 1 . . C
    H22 0.9921 0.9235 0.2510 0.069 Uiso calc R 1 . . H
    C23 0.85580(17) 0.83580(17) 0.19092(12) 0.0506(5) Uani d . 1 . . C
    H23 0.8310 0.8201 0.2347 0.061 Uiso calc R 1 . . H
    Cl1 1.17870(6) 0.75548(8) 0.33639(5) 0.0925(3) Uani d . 1 . . Cl
    Cl2 1.10930(6) 0.99888(7) 0.14842(5) 0.0940(3) Uani d . 1 . . Cl
    N1 1.00751(17) 0.77686(17) 0.39191(12) 0.0650(5) Uani d . 1 . . N
    N2 0.72573(15) 0.67033(16) 0.45914(10) 0.0613(5) Uani d . 1 . . N
    H2A 0.7301 0.6940 0.5060 0.074 Uiso calc R 1 . . H
    N3 0.64482(14) 0.68384(15) 0.32262(10) 0.0544(5) Uani d . 1 . . N
    N4 0.54844(14) 0.73886(14) 0.27325(10) 0.0488(4) Uani d . 1 . . N
    N5 0.40164(15) 0.85715(16) 0.28622(11) 0.0614(5) Uani d . 1 . . N
    H5A 0.3725 0.8598 0.2354 0.074 Uiso calc R 1 . . H
    H5B 0.3710 0.8926 0.3166 0.074 Uiso calc R 1 . . H
    O1 0.43998(13) 0.88196(14) 0.45657(9) 0.0653(4) Uani d . 1 . . O
    O2 0.60505(13) 0.81176(14) 0.53196(9) 0.0617(4) Uani d . 1 . . O
    O3 0.42205(12) 0.79473(13) 0.13597(8) 0.0580(4) Uani d . 1 . . O
    O4 0.52307(12) 0.60854(11) 0.15726(8) 0.0530(4) Uani d . 1 . . O
    O5 0.63461(11) 0.77825(11) 0.16207(8) 0.0497(4) Uani d . 1 . . O
    P1 0.52406(4) 0.73340(4) 0.17534(3) 0.04469(15) Uani d . 1 . . P
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    C1 N1 . 1.308(3) ?
    C1 C2 . 1.362(4) ?
    C1 Cl1 . 1.745(2) ?
    C2 C3 . 1.370(3) ?
    C2 H2 . 0.93 ?
    C3 C4 . 1.380(3) ?
    C3 H3 . 0.93 ?
    C4 C5 . 1.368(3) ?
    C4 C6 . 1.505(3) ?
    C5 N1 . 1.345(3) ?
    C5 H5 . 0.93 ?
    C6 N2 . 1.433(3) ?
    C6 H6A . 0.97 ?
    C6 H6B . 0.97 ?
    C7 N3 . 1.318(3) ?
    C7 N2 . 1.352(3) ?
    C7 C8 . 1.430(3) ?
    C8 C9 . 1.377(3) ?
    C8 C10 . 1.445(3) ?
    C9 N5 . 1.343(3) ?
    C9 N4 . 1.372(2) ?
    C10 O1 . 1.210(2) ?
    C10 O2 . 1.343(3) ?
    C11 O2 . 1.454(3) ?
    C11 C12 . 1.474(4) ?
    C11 H11A . 0.97 ?
    C11 H11B . 0.97 ?
    C12 H12A . 0.96 ?
    C12 H12B . 0.96 ?
    C12 H12C . 0.96 ?
    C13 O4 . 1.449(2) ?
    C13 C14 . 1.528(3) ?
    C13 H13A . 0.97 ?
    C13 H13B . 0.97 ?
    C14 C16 . 1.525(3) ?
    C14 C17 . 1.534(3) ?
    C14 C15 . 1.545(3) ?
    C15 H15A . 0.96 ?
    C15 H15B . 0.96 ?
    C15 H15C . 0.96 ?
    C16 H16A . 0.96 ?
    C16 H16B . 0.96 ?
    C16 H16C . 0.96 ?
    C17 O5 . 1.468(2) ?
    C17 C18 . 1.513(3) ?
    C17 H17 . 0.98 ?
    C18 C23 . 1.386(3) ?
    C18 C19 . 1.388(3) ?
    C19 C20 . 1.382(3) ?
    C19 H19 . 0.93 ?
    C20 C21 . 1.372(3) ?
    C20 H20 . 0.93 ?
    C21 C22 . 1.375(3) ?
    C21 Cl2 . 1.745(2) ?
    C22 C23 . 1.379(3) ?
    C22 H22 . 0.93 ?
    C23 H23 . 0.93 ?
    N2 H2A . 0.86 ?
    N3 N4 . 1.422(2) ?
    N4 P1 . 1.6604(17) ?
    N5 H5A . 0.86 ?
    N5 H5B . 0.86 ?
    O3 P1 . 1.4581(15) ?
    O4 P1 . 1.5554(15) ?
    O5 P1 . 1.5584(13) ?
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_3
    _geom_angle
    _geom_angle_publ_flag
    N1 C1 C2 . . 124.9(2) ?
    N1 C1 Cl1 . . 116.2(2) ?
    C2 C1 Cl1 . . 118.9(2) ?
    C1 C2 C3 . . 117.5(2) ?
    C1 C2 H2 . . 121.2 ?
    C3 C2 H2 . . 121.2 ?
    C2 C3 C4 . . 120.5(2) ?
    C2 C3 H3 . . 119.8 ?
    C4 C3 H3 . . 119.8 ?
    C5 C4 C3 . . 116.2(2) ?
    C5 C4 C6 . . 122.5(2) ?
    C3 C4 C6 . . 121.2(2) ?
    N1 C5 C4 . . 124.8(2) ?
    N1 C5 H5 . . 117.6 ?
    C4 C5 H5 . . 117.6 ?
    N2 C6 C4 . . 115.70(19) ?
    N2 C6 H6A . . 108.4 ?
    C4 C6 H6A . . 108.4 ?
    N2 C6 H6B . . 108.4 ?
    C4 C6 H6B . . 108.4 ?
    H6A C6 H6B . . 107.4 ?
    N3 C7 N2 . . 120.63(19) ?
    N3 C7 C8 . . 112.69(18) ?
    N2 C7 C8 . . 126.65(19) ?
    C9 C8 C7 . . 105.22(17) ?
    C9 C8 C10 . . 124.14(19) ?
    C7 C8 C10 . . 130.6(2) ?
    N5 C9 N4 . . 123.18(18) ?
    N5 C9 C8 . . 129.60(18) ?
    N4 C9 C8 . . 107.22(17) ?
    O1 C10 O2 . . 124.04(19) ?
    O1 C10 C8 . . 124.5(2) ?
    O2 C10 C8 . . 111.46(18) ?
    O2 C11 C12 . . 107.3(2) ?
    O2 C11 H11A . . 110.3 ?
    C12 C11 H11A . . 110.3 ?
    O2 C11 H11B . . 110.3 ?
    C12 C11 H11B . . 110.3 ?
    H11A C11 H11B . . 108.5 ?
    C11 C12 H12A . . 109.5 ?
    C11 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    C11 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    O4 C13 C14 . . 113.85(16) ?
    O4 C13 H13A . . 108.8 ?
    C14 C13 H13A . . 108.8 ?
    O4 C13 H13B . . 108.8 ?
    C14 C13 H13B . . 108.8 ?
    H13A C13 H13B . . 107.7 ?
    C16 C14 C13 . . 111.29(17) ?
    C16 C14 C17 . . 112.75(17) ?
    C13 C14 C17 . . 107.01(17) ?
    C16 C14 C15 . . 110.30(18) ?
    C13 C14 C15 . . 105.92(17) ?
    C17 C14 C15 . . 109.29(16) ?
    C14 C15 H15A . . 109.5 ?
    C14 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    C14 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    C14 C16 H16A . . 109.5 ?
    C14 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C14 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    O5 C17 C18 . . 105.56(14) ?
    O5 C17 C14 . . 110.06(15) ?
    C18 C17 C14 . . 117.65(17) ?
    O5 C17 H17 . . 107.7 ?
    C18 C17 H17 . . 107.7 ?
    C14 C17 H17 . . 107.7 ?
    C23 C18 C19 . . 118.57(18) ?
    C23 C18 C17 . . 121.41(17) ?
    C19 C18 C17 . . 119.93(17) ?
    C20 C19 C18 . . 121.05(19) ?
    C20 C19 H19 . . 119.5 ?
    C18 C19 H19 . . 119.5 ?
    C21 C20 C19 . . 118.8(2) ?
    C21 C20 H20 . . 120.6 ?
    C19 C20 H20 . . 120.6 ?
    C20 C21 C22 . . 121.6(2) ?
    C20 C21 Cl2 . . 119.38(18) ?
    C22 C21 Cl2 . . 119.05(17) ?
    C21 C22 C23 . . 119.08(19) ?
    C21 C22 H22 . . 120.5 ?
    C23 C22 H22 . . 120.5 ?
    C22 C23 C18 . . 120.89(19) ?
    C22 C23 H23 . . 119.6 ?
    C18 C23 H23 . . 119.6 ?
    C1 N1 C5 . . 116.0(2) ?
    C7 N2 C6 . . 120.51(18) ?
    C7 N2 H2A . . 119.7 ?
    C6 N2 H2A . . 119.7 ?
    C7 N3 N4 . . 103.93(16) ?
    C9 N4 N3 . . 110.94(16) ?
    C9 N4 P1 . . 130.28(14) ?
    N3 N4 P1 . . 118.51(12) ?
    C9 N5 H5A . . 120.0 ?
    C9 N5 H5B . . 120.0 ?
    H5A N5 H5B . . 120.0 ?
    C10 O2 C11 . . 118.25(18) ?
    C13 O4 P1 . . 121.26(12) ?
    C17 O5 P1 . . 124.35(12) ?
    O3 P1 O4 . . 116.88(9) y
    O3 P1 O5 . . 115.40(9) y
    O4 P1 O5 . . 105.50(7) y
    O3 P1 N4 . . 109.80(9) y
    O4 P1 N4 . . 103.86(8) y
    O5 P1 N4 . . 104.06(8) y
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
    N1 C1 C2 C3 . . . . -0.6(4) ?
    Cl1 C1 C2 C3 . . . . 178.77(18) ?
    C1 C2 C3 C4 . . . . 0.0(4) ?
    C2 C3 C4 C5 . . . . 0.4(3) ?
    C2 C3 C4 C6 . . . . -179.4(2) ?
    C3 C4 C5 N1 . . . . -0.5(3) ?
    C6 C4 C5 N1 . . . . 179.4(2) ?
    C5 C4 C6 N2 . . . . 13.2(3) ?
    C3 C4 C6 N2 . . . . -166.9(2) ?
    N3 C7 C8 C9 . . . . 0.6(2) ?
    N2 C7 C8 C9 . . . . -177.8(2) ?
    N3 C7 C8 C10 . . . . 179.7(2) ?
    N2 C7 C8 C10 . . . . 1.2(4) ?
    C7 C8 C9 N5 . . . . 179.8(2) ?
    C10 C8 C9 N5 . . . . 0.7(3) ?
    C7 C8 C9 N4 . . . . -0.5(2) ?
    C10 C8 C9 N4 . . . . -179.62(18) ?
    C9 C8 C10 O1 . . . . 6.1(3) ?
    C7 C8 C10 O1 . . . . -172.8(2) ?
    C9 C8 C10 O2 . . . . -173.37(18) ?
    C7 C8 C10 O2 . . . . 7.7(3) ?
    O4 C13 C14 C16 . . . . 64.7(2) ?
    O4 C13 C14 C17 . . . . -58.9(2) ?
    O4 C13 C14 C15 . . . . -175.43(17) ?
    C16 C14 C17 O5 . . . . -66.1(2) ?
    C13 C14 C17 O5 . . . . 56.6(2) ?
    C15 C14 C17 O5 . . . . 170.85(16) ?
    C16 C14 C17 C18 . . . . 54.8(2) ?
    C13 C14 C17 C18 . . . . 177.50(16) ?
    C15 C14 C17 C18 . . . . -68.2(2) ?
    O5 C17 C18 C23 . . . . 31.9(2) ?
    C14 C17 C18 C23 . . . . -91.3(2) ?
    O5 C17 C18 C19 . . . . -144.65(18) ?
    C14 C17 C18 C19 . . . . 92.1(2) ?
    C23 C18 C19 C20 . . . . 1.1(3) ?
    C17 C18 C19 C20 . . . . 177.80(18) ?
    C18 C19 C20 C21 . . . . -1.3(3) ?
    C19 C20 C21 C22 . . . . 0.9(3) ?
    C19 C20 C21 Cl2 . . . . -179.19(16) ?
    C20 C21 C22 C23 . . . . -0.2(3) ?
    Cl2 C21 C22 C23 . . . . 179.80(17) ?
    C21 C22 C23 C18 . . . . 0.1(3) ?
    C19 C18 C23 C22 . . . . -0.5(3) ?
    C17 C18 C23 C22 . . . . -177.12(19) ?
    C2 C1 N1 C5 . . . . 0.6(3) ?
    Cl1 C1 N1 C5 . . . . -178.79(16) ?
    C4 C5 N1 C1 . . . . 0.0(3) ?
    N3 C7 N2 C6 . . . . -6.7(3) ?
    C8 C7 N2 C6 . . . . 171.6(2) ?
    C4 C6 N2 C7 . . . . 77.0(3) ?
    N2 C7 N3 N4 . . . . 178.07(19) ?
    C8 C7 N3 N4 . . . . -0.5(2) ?
    N5 C9 N4 N3 . . . . 179.95(19) ?
    C8 C9 N4 N3 . . . . 0.2(2) ?
    N5 C9 N4 P1 . . . . 6.1(3) ?
    C8 C9 N4 P1 . . . . -173.61(15) ?
    C7 N3 N4 C9 . . . . 0.1(2) ?
    C7 N3 N4 P1 . . . . 174.80(14) ?
    O1 C10 O2 C11 . . . . -3.7(3) ?
    C8 C10 O2 C11 . . . . 175.73(18) ?
    C12 C11 O2 C10 . . . . -143.2(2) ?
    C14 C13 O4 P1 . . . . 48.4(2) ?
    C18 C17 O5 P1 . . . . -175.99(12) ?
    C14 C17 O5 P1 . . . . -48.1(2) ?
    C13 O4 P1 O3 . . . . 99.66(16) ?
    C13 O4 P1 O5 . . . . -30.10(17) ?
    C13 O4 P1 N4 . . . . -139.25(15) ?
    C17 O5 P1 O3 . . . . -99.29(16) ?
    C17 O5 P1 O4 . . . . 31.34(16) ?
    C17 O5 P1 N4 . . . . 140.35(15) ?
    C9 N4 P1 O3 . . . . -6.5(2) ?
    N3 N4 P1 O3 . . . . -179.92(14) ?
    C9 N4 P1 O4 . . . . -132.18(18) ?
    N3 N4 P1 O4 . . . . 54.36(16) ?
    C9 N4 P1 O5 . . . . 117.61(19) ?
    N3 N4 P1 O5 . . . . -55.86(16) ?
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_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    C11 H11B O1 3_676 0.97 2.52 3.290(3) 136 y
    C16 H16A N3 . 0.96 2.54 3.486(3) 167 y
    N2 H2A O2 . 0.86 2.26 2.829(2) 124 y
    N5 H5A O3 . 0.86 2.17 2.834(2) 134 y
    N5 H5B O1 . 0.86 2.36 2.909(2) 122 y
    C6 H6A Cg1 2_645 0.97 2.80 3.680(3) 152 y
    C11 H11A Cg1 4_576 0.97 2.89 3.753(3) 149 y
